EP2928296A1 - Use of substituted 1-(aryl ethynyl)-, 1-(heteroaryl ethynyl)-, 1-(heterocyclyl ethynyl)- and 1-(cyloalkenyl ethynyl)-cyclohexanols as active agents against abiotic plant stress - Google Patents
Use of substituted 1-(aryl ethynyl)-, 1-(heteroaryl ethynyl)-, 1-(heterocyclyl ethynyl)- and 1-(cyloalkenyl ethynyl)-cyclohexanols as active agents against abiotic plant stressInfo
- Publication number
- EP2928296A1 EP2928296A1 EP13798695.6A EP13798695A EP2928296A1 EP 2928296 A1 EP2928296 A1 EP 2928296A1 EP 13798695 A EP13798695 A EP 13798695A EP 2928296 A1 EP2928296 A1 EP 2928296A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- alkyl
- alkoxy
- aryl
- alkoxycarbonyl
- alkylaminocarbonyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 title abstract description 13
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 title abstract description 7
- 239000013543 active substance Substances 0.000 title description 2
- 230000001965 increasing effect Effects 0.000 claims abstract description 28
- 150000003839 salts Chemical class 0.000 claims abstract description 25
- 230000036579 abiotic stress Effects 0.000 claims abstract description 24
- 230000035882 stress Effects 0.000 claims abstract description 24
- -1 haloalkylthioalkyl Chemical group 0.000 claims description 513
- 125000000217 alkyl group Chemical group 0.000 claims description 488
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 260
- 125000003545 alkoxy group Chemical group 0.000 claims description 206
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 203
- 125000003118 aryl group Chemical group 0.000 claims description 191
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 144
- 125000001072 heteroaryl group Chemical group 0.000 claims description 141
- 239000001257 hydrogen Substances 0.000 claims description 135
- 229910052739 hydrogen Inorganic materials 0.000 claims description 135
- 125000000623 heterocyclic group Chemical group 0.000 claims description 124
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 101
- 150000002431 hydrogen Chemical class 0.000 claims description 100
- 229910052760 oxygen Inorganic materials 0.000 claims description 88
- 229910052736 halogen Inorganic materials 0.000 claims description 83
- 150000002367 halogens Chemical class 0.000 claims description 83
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 82
- 229910052717 sulfur Inorganic materials 0.000 claims description 80
- 239000000460 chlorine Substances 0.000 claims description 78
- 125000001188 haloalkyl group Chemical group 0.000 claims description 78
- 229910052801 chlorine Inorganic materials 0.000 claims description 72
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 72
- 125000004414 alkyl thio group Chemical group 0.000 claims description 70
- 229910052731 fluorine Inorganic materials 0.000 claims description 68
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims description 68
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 67
- 239000011737 fluorine Substances 0.000 claims description 66
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 66
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 64
- 229910052794 bromium Inorganic materials 0.000 claims description 64
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 63
- 125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 63
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 62
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 62
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 61
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 61
- 239000001301 oxygen Substances 0.000 claims description 61
- 239000011593 sulfur Substances 0.000 claims description 61
- 125000003342 alkenyl group Chemical group 0.000 claims description 59
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 58
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 50
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 46
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 45
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 43
- 239000007983 Tris buffer Substances 0.000 claims description 42
- 125000000304 alkynyl group Chemical group 0.000 claims description 42
- 150000001875 compounds Chemical class 0.000 claims description 42
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 41
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 40
- 125000004104 aryloxy group Chemical group 0.000 claims description 37
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 37
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 35
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 34
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 34
- 229920006395 saturated elastomer Polymers 0.000 claims description 33
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 31
- 229910052757 nitrogen Inorganic materials 0.000 claims description 31
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 30
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 29
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 28
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 28
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 28
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 25
- 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims description 25
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 24
- 125000005224 heteroarylcarbonylamino group Chemical group 0.000 claims description 24
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims description 23
- 125000003282 alkyl amino group Chemical group 0.000 claims description 23
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 23
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 23
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 22
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 21
- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 21
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims description 21
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 21
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 21
- 125000005141 aryl amino sulfonyl group Chemical group 0.000 claims description 20
- 125000005199 aryl carbonyloxy group Chemical group 0.000 claims description 20
- 125000005366 cycloalkylthio group Chemical group 0.000 claims description 20
- 239000003337 fertilizer Substances 0.000 claims description 20
- 125000005204 heteroarylcarbonyloxy group Chemical group 0.000 claims description 20
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 20
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 19
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 19
- 125000005167 cycloalkylaminocarbonyl group Chemical group 0.000 claims description 19
- 239000000243 solution Substances 0.000 claims description 19
- 125000004434 sulfur atom Chemical group 0.000 claims description 19
- 125000005089 alkenylaminocarbonyl group Chemical group 0.000 claims description 18
- 125000005225 alkynyloxycarbonyl group Chemical group 0.000 claims description 18
- 125000005110 aryl thio group Chemical group 0.000 claims description 18
- 125000005149 cycloalkylsulfinyl group Chemical group 0.000 claims description 18
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 18
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 17
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 17
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 17
- 125000004429 atom Chemical group 0.000 claims description 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
- 125000006416 CBr Chemical group BrC* 0.000 claims description 15
- 125000006414 CCl Chemical group ClC* 0.000 claims description 15
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 15
- 125000006598 aminocarbonylamino group Chemical group 0.000 claims description 15
- 125000004468 heterocyclylthio group Chemical group 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 14
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 14
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 14
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 14
- 125000005150 heteroarylsulfinyl group Chemical group 0.000 claims description 14
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 13
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical class OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 12
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 12
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 12
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 12
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 12
- 125000005125 aryl alkyl amino carbonyl group Chemical group 0.000 claims description 12
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 12
- 125000005226 heteroaryloxycarbonyl group Chemical group 0.000 claims description 12
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 11
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 11
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 11
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 11
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 11
- 239000007921 spray Substances 0.000 claims description 11
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 11
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 10
- 238000011282 treatment Methods 0.000 claims description 10
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 9
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 9
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 9
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 9
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 9
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims description 8
- 125000004946 alkenylalkyl group Chemical group 0.000 claims description 8
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 125000004994 halo alkoxy alkyl group Chemical group 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 7
- 125000006554 (C4-C8) cycloalkenyl group Chemical group 0.000 claims description 7
- 125000005038 alkynylalkyl group Chemical group 0.000 claims description 7
- 239000011575 calcium Substances 0.000 claims description 7
- 125000005347 halocycloalkyl group Chemical group 0.000 claims description 7
- 125000005368 heteroarylthio group Chemical group 0.000 claims description 7
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 7
- 235000015097 nutrients Nutrition 0.000 claims description 7
- 125000006648 (C1-C8) haloalkyl group Chemical group 0.000 claims description 6
- 229910014585 C2-Ce Inorganic materials 0.000 claims description 6
- 206010009944 Colon cancer Diseases 0.000 claims description 6
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 6
- 125000004949 alkyl amino carbonyl amino group Chemical group 0.000 claims description 6
- 125000005201 cycloalkylcarbonyloxy group Chemical group 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- 125000006799 (C2-C6) alkenylamino group Chemical group 0.000 claims description 5
- 125000006644 (C2-C6) haloalkynyl group Chemical group 0.000 claims description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 5
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 5
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 5
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 5
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 5
- 125000005169 cycloalkylcarbonylamino group Chemical group 0.000 claims description 5
- 239000004009 herbicide Substances 0.000 claims description 5
- 239000011574 phosphorus Substances 0.000 claims description 5
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 4
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 4
- 125000006323 alkenyl amino group Chemical group 0.000 claims description 4
- 125000004694 alkoxyaminocarbonyl group Chemical group 0.000 claims description 4
- 125000005145 cycloalkylaminosulfonyl group Chemical group 0.000 claims description 4
- 239000000417 fungicide Substances 0.000 claims description 4
- 239000003630 growth substance Substances 0.000 claims description 4
- 125000005221 halo alkyl carbonyl amino group Chemical group 0.000 claims description 4
- 125000004661 haloalkylaminosulfonyl group Chemical group 0.000 claims description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- 239000011707 mineral Substances 0.000 claims description 4
- 239000002689 soil Substances 0.000 claims description 4
- 125000006625 (C3-C8) cycloalkyloxy group Chemical group 0.000 claims description 3
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims description 3
- 125000005015 aryl alkynyl group Chemical group 0.000 claims description 3
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 3
- 230000008641 drought stress Effects 0.000 claims description 3
- 125000006809 haloalkylaminocarbonyl group Chemical group 0.000 claims description 3
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 3
- 239000002917 insecticide Substances 0.000 claims description 3
- 230000008723 osmotic stress Effects 0.000 claims description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
- 230000000895 acaricidal effect Effects 0.000 claims description 2
- 239000000642 acaricide Substances 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 125000004689 alkyl amino carbonyl alkyl group Chemical group 0.000 claims description 2
- 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims description 2
- 230000000844 anti-bacterial effect Effects 0.000 claims description 2
- 125000005126 aryl alkyl carbonyl amino group Chemical group 0.000 claims description 2
- 125000005324 aryloxy alkyloxy group Chemical group 0.000 claims description 2
- 239000005667 attractant Substances 0.000 claims description 2
- 239000003899 bactericide agent Substances 0.000 claims description 2
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 2
- 125000004690 haloalkylaminocarbonylalkyl group Chemical group 0.000 claims description 2
- 230000008642 heat stress Effects 0.000 claims description 2
- 239000005645 nematicide Substances 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 241000894007 species Species 0.000 claims description 2
- 125000005389 trialkylsiloxy group Chemical group 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 26
- 231100000252 nontoxic Toxicity 0.000 claims 2
- 230000003000 nontoxic effect Effects 0.000 claims 2
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 230000008645 cold stress Effects 0.000 claims 1
- 230000000875 corresponding effect Effects 0.000 claims 1
- 125000005326 heteroaryloxy alkyl group Chemical group 0.000 claims 1
- 230000004962 physiological condition Effects 0.000 claims 1
- 244000045561 useful plants Species 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 81
- 238000005160 1H NMR spectroscopy Methods 0.000 description 64
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 53
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 43
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
- 150000003254 radicals Chemical class 0.000 description 24
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 23
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 22
- 238000005481 NMR spectroscopy Methods 0.000 description 22
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 22
- 125000004432 carbon atom Chemical group C* 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 18
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 18
- 230000002829 reductive effect Effects 0.000 description 16
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 description 15
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 15
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
- 230000000694 effects Effects 0.000 description 13
- 239000008346 aqueous phase Substances 0.000 description 11
- 239000012043 crude product Substances 0.000 description 11
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 11
- 235000019341 magnesium sulphate Nutrition 0.000 description 11
- 239000012074 organic phase Substances 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 229910052786 argon Inorganic materials 0.000 description 9
- 238000011097 chromatography purification Methods 0.000 description 9
- 230000036541 health Effects 0.000 description 9
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 9
- 239000003880 polar aprotic solvent Substances 0.000 description 9
- 239000002585 base Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 125000001153 fluoro group Chemical group F* 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 125000006730 (C2-C5) alkynyl group Chemical group 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 235000013399 edible fruits Nutrition 0.000 description 7
- JLIDBLDQVAYHNE-YKALOCIXSA-N (+)-Abscisic acid Chemical compound OC(=O)/C=C(/C)\C=C\[C@@]1(O)C(C)=CC(=O)CC1(C)C JLIDBLDQVAYHNE-YKALOCIXSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 229940043279 diisopropylamine Drugs 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 6
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 6
- 125000006256 n-propyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC(*)=O 0.000 description 6
- 230000008635 plant growth Effects 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 108090000623 proteins and genes Proteins 0.000 description 6
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 5
- PQQOQXUYGRGYEK-UHFFFAOYSA-N 1-ethynyl-2,2,6-trimethylcyclohexan-1-ol Chemical compound CC1CCCC(C)(C)C1(O)C#C PQQOQXUYGRGYEK-UHFFFAOYSA-N 0.000 description 5
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 5
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 5
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- ZPVOLGVTNLDBFI-UHFFFAOYSA-N (±)-2,2,6-trimethylcyclohexanone Chemical compound CC1CCCC(C)(C)C1=O ZPVOLGVTNLDBFI-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical group [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 4
- 125000003636 chemical group Chemical group 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- 125000004043 oxo group Chemical group O=* 0.000 description 4
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 235000018102 proteins Nutrition 0.000 description 4
- 102000004169 proteins and genes Human genes 0.000 description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
- 125000003107 substituted aryl group Chemical group 0.000 description 4
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 4
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- 125000004751 (C1-C6) haloalkylaminosulfonyl group Chemical group 0.000 description 3
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
- NXFFJDQHYLNEJK-UHFFFAOYSA-N 2-[4-[(4-chlorophenyl)methyl]-7-fluoro-5-methylsulfonyl-2,3-dihydro-1h-cyclopenta[b]indol-3-yl]acetic acid Chemical compound C1=2C(S(=O)(=O)C)=CC(F)=CC=2C=2CCC(CC(O)=O)C=2N1CC1=CC=C(Cl)C=C1 NXFFJDQHYLNEJK-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- 235000002566 Capsicum Nutrition 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- BMXAEYUCMLOGFN-UHFFFAOYSA-N OC1(C(CCCC1C)(C)C)C#CC1=C(C(=O)O)C=CC=C1 Chemical compound OC1(C(CCCC1C)(C)C)C#CC1=C(C(=O)O)C=CC=C1 BMXAEYUCMLOGFN-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 3
- 244000046052 Phaseolus vulgaris Species 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000011054 acetic acid Nutrition 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 125000002837 carbocyclic group Chemical group 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 230000007123 defense Effects 0.000 description 3
- FCRACOPGPMPSHN-UHFFFAOYSA-N desoxyabscisic acid Natural products OC(=O)C=C(C)C=CC1C(C)=CC(=O)CC1(C)C FCRACOPGPMPSHN-UHFFFAOYSA-N 0.000 description 3
- 125000004663 dialkyl amino group Chemical group 0.000 description 3
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 3
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 229910052738 indium Inorganic materials 0.000 description 3
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 3
- MISWBHWTGCHVND-UHFFFAOYSA-N methyl 2-[2-(1-hydroxy-2,2,6-trimethylcyclohexyl)ethynyl]benzoate Chemical compound COC(=O)C1=CC=CC=C1C#CC1(O)C(C)(C)CCCC1C MISWBHWTGCHVND-UHFFFAOYSA-N 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 244000052769 pathogen Species 0.000 description 3
- 230000001717 pathogenic effect Effects 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
- 239000003642 reactive oxygen metabolite Substances 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 125000006413 ring segment Chemical group 0.000 description 3
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 3
- 229910052723 transition metal Inorganic materials 0.000 description 3
- 150000003624 transition metals Chemical class 0.000 description 3
- 125000002827 triflate group Chemical class FC(S(=O)(=O)O*)(F)F 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- 125000006624 (C1-C6) alkoxycarbonylamino group Chemical group 0.000 description 2
- 125000004750 (C1-C6) alkylaminosulfonyl group Chemical group 0.000 description 2
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 description 2
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 description 2
- LBEMYSKBSYEVAG-UHFFFAOYSA-N 1-(2-phenylethynyl)cyclohexan-1-ol Chemical class C=1C=CC=CC=1C#CC1(O)CCCCC1 LBEMYSKBSYEVAG-UHFFFAOYSA-N 0.000 description 2
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 2
- LLIDRMMQRLVSAV-UHFFFAOYSA-N 1-[2-(2-methoxyphenyl)ethynyl]-2,2,6-trimethylcyclohexan-1-ol Chemical compound COC1=CC=CC=C1C#CC1(O)C(C)(C)CCCC1C LLIDRMMQRLVSAV-UHFFFAOYSA-N 0.000 description 2
- UADWWWKOGCAZLN-UHFFFAOYSA-N 1-ethynyl-2,6-dimethylcyclohexan-1-ol Chemical compound CC1CCCC(C)C1(O)C#C UADWWWKOGCAZLN-UHFFFAOYSA-N 0.000 description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 2
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- 125000004487 4-tetrahydropyranyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 244000075850 Avena orientalis Species 0.000 description 2
- 235000007319 Avena orientalis Nutrition 0.000 description 2
- 235000016068 Berberis vulgaris Nutrition 0.000 description 2
- 241000335053 Beta vulgaris Species 0.000 description 2
- 240000007124 Brassica oleracea Species 0.000 description 2
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 2
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 2
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 2
- 125000006519 CCH3 Chemical group 0.000 description 2
- DASQIKOOFDJYKA-UHFFFAOYSA-N CCIF Chemical compound CCIF DASQIKOOFDJYKA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241000218631 Coniferophyta Species 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 241000219112 Cucumis Species 0.000 description 2
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 description 2
- 240000008067 Cucumis sativus Species 0.000 description 2
- 239000005696 Diammonium phosphate Substances 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 241000219146 Gossypium Species 0.000 description 2
- 102000002812 Heat-Shock Proteins Human genes 0.000 description 2
- 108010004889 Heat-Shock Proteins Proteins 0.000 description 2
- 240000005979 Hordeum vulgare Species 0.000 description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical group [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 244000070406 Malus silvestris Species 0.000 description 2
- 102000005431 Molecular Chaperones Human genes 0.000 description 2
- 108010006519 Molecular Chaperones Proteins 0.000 description 2
- LRSWPRWXDXQNFA-UHFFFAOYSA-N N#CS[S+]=C=NF Chemical compound N#CS[S+]=C=NF LRSWPRWXDXQNFA-UHFFFAOYSA-N 0.000 description 2
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 2
- 244000061176 Nicotiana tabacum Species 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000006002 Pepper Substances 0.000 description 2
- 102000004160 Phosphoric Monoester Hydrolases Human genes 0.000 description 2
- 108090000608 Phosphoric Monoester Hydrolases Proteins 0.000 description 2
- 241000722363 Piper Species 0.000 description 2
- 235000016761 Piper aduncum Nutrition 0.000 description 2
- 235000017804 Piper guineense Nutrition 0.000 description 2
- 235000008184 Piper nigrum Nutrition 0.000 description 2
- 102000012338 Poly(ADP-ribose) Polymerases Human genes 0.000 description 2
- 108010061844 Poly(ADP-ribose) Polymerases Proteins 0.000 description 2
- 102100032347 Poly(ADP-ribose) glycohydrolase Human genes 0.000 description 2
- 229920000776 Poly(Adenosine diphosphate-ribose) polymerase Polymers 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 241000220324 Pyrus Species 0.000 description 2
- 235000007238 Secale cereale Nutrition 0.000 description 2
- 244000082988 Secale cereale Species 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- 244000061458 Solanum melongena Species 0.000 description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- 102000040945 Transcription factor Human genes 0.000 description 2
- 108091023040 Transcription factor Proteins 0.000 description 2
- 235000019714 Triticale Nutrition 0.000 description 2
- 241000209140 Triticum Species 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 150000003529 abscisic acid derivatives Chemical class 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 125000001118 alkylidene group Chemical group 0.000 description 2
- 125000005282 allenyl group Chemical group 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- LFVGISIMTYGQHF-UHFFFAOYSA-N ammonium dihydrogen phosphate Chemical compound [NH4+].OP(O)([O-])=O LFVGISIMTYGQHF-UHFFFAOYSA-N 0.000 description 2
- 229910000387 ammonium dihydrogen phosphate Inorganic materials 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 235000021028 berry Nutrition 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- 238000013375 chromatographic separation Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- 244000038559 crop plants Species 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 229910000388 diammonium phosphate Inorganic materials 0.000 description 2
- 235000019838 diammonium phosphate Nutrition 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- VUPKGFBOKBGHFZ-UHFFFAOYSA-N dipropyl carbonate Chemical group CCCOC(=O)OCCC VUPKGFBOKBGHFZ-UHFFFAOYSA-N 0.000 description 2
- KVLJUFSHIVZRAU-UHFFFAOYSA-N ethyl 1-[2-[2-(1-hydroxy-2,2,6-trimethylcyclohexyl)ethynyl]benzoyl]piperidine-2-carboxylate Chemical compound CCOC(=O)C1CCCCN1C(=O)C1=CC=CC=C1C#CC1(O)C(C)(C)CCCC1C KVLJUFSHIVZRAU-UHFFFAOYSA-N 0.000 description 2
- ZFLPJHGXVFJDCI-UHFFFAOYSA-N ethyl 2-(trifluoromethylsulfonyloxy)cyclopentene-1-carboxylate Chemical compound CCOC(=O)C1=C(OS(=O)(=O)C(F)(F)F)CCC1 ZFLPJHGXVFJDCI-UHFFFAOYSA-N 0.000 description 2
- 125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000035784 germination Effects 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 description 2
- 230000008821 health effect Effects 0.000 description 2
- 125000005114 heteroarylalkoxy group Chemical group 0.000 description 2
- PSCMQHVBLHHWTO-UHFFFAOYSA-K indium(iii) chloride Chemical compound Cl[In](Cl)Cl PSCMQHVBLHHWTO-UHFFFAOYSA-K 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- ZNJFBWYDHIGLCU-HWKXXFMVSA-N jasmonic acid Chemical compound CC\C=C/C[C@@H]1[C@@H](CC(O)=O)CCC1=O ZNJFBWYDHIGLCU-HWKXXFMVSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- WMWSRIHFAVOHSW-UHFFFAOYSA-N lithium;ethane-1,2-diamine;ethyne Chemical compound [Li+].[C-]#C.NCCN WMWSRIHFAVOHSW-UHFFFAOYSA-N 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 230000001404 mediated effect Effects 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- DCVOWEJPSQVRER-UHFFFAOYSA-N methyl 2-[2-(1-acetyloxy-2,2,6-trimethylcyclohexyl)ethynyl]benzoate Chemical compound COC(=O)C1=CC=CC=C1C#CC1(OC(C)=O)C(C)(C)CCCC1C DCVOWEJPSQVRER-UHFFFAOYSA-N 0.000 description 2
- BXXLTVBTDZXPTN-UHFFFAOYSA-N methyl 2-iodobenzoate Chemical compound COC(=O)C1=CC=CC=C1I BXXLTVBTDZXPTN-UHFFFAOYSA-N 0.000 description 2
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 2
- 235000019837 monoammonium phosphate Nutrition 0.000 description 2
- 239000006012 monoammonium phosphate Substances 0.000 description 2
- 125000006682 monohaloalkyl group Chemical group 0.000 description 2
- 125000006257 n-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])OC(*)=O 0.000 description 2
- 125000005933 neopentyloxycarbonyl group Chemical group 0.000 description 2
- 150000002823 nitrates Chemical class 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 230000000065 osmolyte Effects 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- 230000029553 photosynthesis Effects 0.000 description 2
- 238000010672 photosynthesis Methods 0.000 description 2
- 108010078356 poly ADP-ribose glycohydrolase Proteins 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 159000000001 potassium salts Chemical class 0.000 description 2
- 239000003586 protic polar solvent Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 150000003248 quinolines Chemical class 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 229960004889 salicylic acid Drugs 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- 238000004611 spectroscopical analysis Methods 0.000 description 2
- 239000004575 stone Substances 0.000 description 2
- 238000005728 strengthening Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- 230000021918 systemic acquired resistance Effects 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- JKNHZOAONLKYQL-UHFFFAOYSA-K tribromoindigane Chemical compound Br[In](Br)Br JKNHZOAONLKYQL-UHFFFAOYSA-K 0.000 description 2
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 2
- CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 241000228158 x Triticosecale Species 0.000 description 2
- XRNXMVZXLFUIQI-RPMWBOEFSA-N (2z,4e)-5-[(1s,6s)-1-hydroxy-2,2,6-trimethylcyclohexyl]penta-2,4-dienoic acid Chemical compound C[C@H]1CCCC(C)(C)[C@@]1(O)\C=C\C=C/C(O)=O XRNXMVZXLFUIQI-RPMWBOEFSA-N 0.000 description 1
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 description 1
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 description 1
- 125000006531 (C2-C5) alkyl group Chemical group 0.000 description 1
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 description 1
- 125000006636 (C3-C8) cycloalkylcarbonyl group Chemical group 0.000 description 1
- SDVVLIIVFBKBMG-ONEGZZNKSA-N (E)-penta-2,4-dienoic acid Chemical compound OC(=O)\C=C\C=C SDVVLIIVFBKBMG-ONEGZZNKSA-N 0.000 description 1
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- 125000001607 1,2,3-triazol-1-yl group Chemical group [*]N1N=NC([H])=C1[H] 0.000 description 1
- 125000001359 1,2,3-triazol-4-yl group Chemical group [H]N1N=NC([*])=C1[H] 0.000 description 1
- 125000001766 1,2,4-oxadiazol-3-yl group Chemical group [H]C1=NC(*)=NO1 0.000 description 1
- 125000004505 1,2,4-oxadiazol-5-yl group Chemical group O1N=CN=C1* 0.000 description 1
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 description 1
- 125000001305 1,2,4-triazol-3-yl group Chemical group [H]N1N=C([*])N=C1[H] 0.000 description 1
- 125000001401 1,2,4-triazol-4-yl group Chemical group N=1N=C([H])N([*])C=1[H] 0.000 description 1
- 125000004509 1,3,4-oxadiazol-2-yl group Chemical group O1C(=NN=C1)* 0.000 description 1
- 125000004317 1,3,5-triazin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=N1 0.000 description 1
- 125000004227 1,3-benzoxazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)OC2=C1[H] 0.000 description 1
- 125000000196 1,4-pentadienyl group Chemical group [H]C([*])=C([H])C([H])([H])C([H])=C([H])[H] 0.000 description 1
- VMLKTERJLVWEJJ-UHFFFAOYSA-N 1,5-naphthyridine Chemical compound C1=CC=NC2=CC=CN=C21 VMLKTERJLVWEJJ-UHFFFAOYSA-N 0.000 description 1
- VSOSXKMEQPYESP-UHFFFAOYSA-N 1,6-naphthyridine Chemical compound C1=CN=CC2=CC=CN=C21 VSOSXKMEQPYESP-UHFFFAOYSA-N 0.000 description 1
- MXBVNILGVJVVMH-UHFFFAOYSA-N 1,7-naphthyridine Chemical compound C1=NC=CC2=CC=CN=C21 MXBVNILGVJVVMH-UHFFFAOYSA-N 0.000 description 1
- BAPDWOBBGGGGOC-UHFFFAOYSA-N 1,8-naphthyridine;2,6-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21.N1=CC=C2C=NC=CC2=C1 BAPDWOBBGGGGOC-UHFFFAOYSA-N 0.000 description 1
- OFXKISIOBRRYFP-UHFFFAOYSA-N 1-[2-(3-methoxyphenyl)ethynyl]-2,6-dimethylcyclohexan-1-ol Chemical compound COC1=CC=CC(C#CC2(O)C(CCCC2C)C)=C1 OFXKISIOBRRYFP-UHFFFAOYSA-N 0.000 description 1
- AWFABMMGRQSUOB-UHFFFAOYSA-N 1-[2-(4-methoxy-3-propan-2-ylphenyl)ethynyl]-2,2,6-trimethylcyclohexan-1-ol Chemical compound C1=C(C(C)C)C(OC)=CC=C1C#CC1(O)C(C)(C)CCCC1C AWFABMMGRQSUOB-UHFFFAOYSA-N 0.000 description 1
- BPQALNFEAWBTOV-UHFFFAOYSA-N 1-[2-(4-methoxyphenyl)ethynyl]-2,2,6-trimethylcyclohexan-1-ol Chemical compound C1=CC(OC)=CC=C1C#CC1(O)C(C)(C)CCCC1C BPQALNFEAWBTOV-UHFFFAOYSA-N 0.000 description 1
- 125000005939 1-azabicyclo[2.2.1]heptyl group Chemical group 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- QYLFHLNFIHBCPR-UHFFFAOYSA-N 1-ethynylcyclohexan-1-ol Chemical class C#CC1(O)CCCCC1 QYLFHLNFIHBCPR-UHFFFAOYSA-N 0.000 description 1
- DVQWNQBEUKXONL-UHFFFAOYSA-N 1-iodo-2-methoxybenzene Chemical compound COC1=CC=CC=C1I DVQWNQBEUKXONL-UHFFFAOYSA-N 0.000 description 1
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- STVOFKFJYAPPFA-UHFFFAOYSA-N 2,6-dimethyl-1-(2-phenylethynyl)cyclohexan-1-ol Chemical compound CC1CCCC(C)C1(O)C#CC1=CC=CC=C1 STVOFKFJYAPPFA-UHFFFAOYSA-N 0.000 description 1
- AILVYPLQKCQNJC-UHFFFAOYSA-N 2,6-dimethylcyclohexan-1-one Chemical compound CC1CCCC(C)C1=O AILVYPLQKCQNJC-UHFFFAOYSA-N 0.000 description 1
- ZUYKJZQOPXDNOK-UHFFFAOYSA-N 2-(ethylamino)-2-thiophen-2-ylcyclohexan-1-one;hydrochloride Chemical class Cl.C=1C=CSC=1C1(NCC)CCCCC1=O ZUYKJZQOPXDNOK-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- WDSPKJNTRYGSBV-UHFFFAOYSA-N 2-methyl-1-(2-phenylethynyl)cyclohexan-1-ol Chemical compound CC1CCCCC1(O)C#CC1=CC=CC=C1 WDSPKJNTRYGSBV-UHFFFAOYSA-N 0.000 description 1
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 1
- FMZVCQJWNJNKEW-UHFFFAOYSA-N 2-phenylethynyl cyclohexanecarboxylate Chemical compound C1(CCCCC1)C(=O)OC#CC1=CC=CC=C1 FMZVCQJWNJNKEW-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 description 1
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- MSBGDLOZNZOWIQ-UHFFFAOYSA-N 3,4,5,6-tetrahydropyridazine Chemical compound C1CCN=NC1 MSBGDLOZNZOWIQ-UHFFFAOYSA-N 0.000 description 1
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- OCCVYKKPZRENDP-UHFFFAOYSA-N 3-methyl-5-(1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-6-yl)penta-2,4-dienoic acid Chemical class C1CCC(C)(C)C2(C=CC(C)=CC(O)=O)C1(C)O2 OCCVYKKPZRENDP-UHFFFAOYSA-N 0.000 description 1
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- QRAOZQGIUIDZQZ-UHFFFAOYSA-N 4-methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1,4-benzoxazine Chemical compound C=1C=C2N(C)CCOC2=CC=1B1OC(C)(C)C(C)(C)O1 QRAOZQGIUIDZQZ-UHFFFAOYSA-N 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical class O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 description 1
- 241000218642 Abies Species 0.000 description 1
- 241000208140 Acer Species 0.000 description 1
- 241000157282 Aesculus Species 0.000 description 1
- 102000005369 Aldehyde Dehydrogenase Human genes 0.000 description 1
- 108020002663 Aldehyde Dehydrogenase Proteins 0.000 description 1
- 244000291564 Allium cepa Species 0.000 description 1
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000004254 Ammonium phosphate Substances 0.000 description 1
- 244000144725 Amygdalus communis Species 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 244000003416 Asparagus officinalis Species 0.000 description 1
- 235000005340 Asparagus officinalis Nutrition 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- 241000167854 Bourreria succulenta Species 0.000 description 1
- 241000219198 Brassica Species 0.000 description 1
- 235000003351 Brassica cretica Nutrition 0.000 description 1
- 240000002791 Brassica napus Species 0.000 description 1
- 235000006008 Brassica napus var napus Nutrition 0.000 description 1
- 235000003343 Brassica rupestris Nutrition 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
- 240000004160 Capsicum annuum Species 0.000 description 1
- 235000008534 Capsicum annuum var annuum Nutrition 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 101150065749 Churc1 gene Proteins 0.000 description 1
- 241000723347 Cinnamomum Species 0.000 description 1
- 241000723346 Cinnamomum camphora Species 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- 241001672694 Citrus reticulata Species 0.000 description 1
- 240000000560 Citrus x paradisi Species 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 240000007154 Coffea arabica Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 240000000491 Corchorus aestuans Species 0.000 description 1
- 235000011777 Corchorus aestuans Nutrition 0.000 description 1
- 235000010862 Corchorus capsularis Nutrition 0.000 description 1
- 235000009849 Cucumis sativus Nutrition 0.000 description 1
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 1
- 235000009854 Cucurbita moschata Nutrition 0.000 description 1
- 240000001980 Cucurbita pepo Species 0.000 description 1
- 235000009852 Cucurbita pepo Nutrition 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 102000018832 Cytochromes Human genes 0.000 description 1
- 108010052832 Cytochromes Proteins 0.000 description 1
- 235000002767 Daucus carota Nutrition 0.000 description 1
- 244000000626 Daucus carota Species 0.000 description 1
- 244000236655 Diospyros kaki Species 0.000 description 1
- 235000008597 Diospyros kaki Nutrition 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 244000080545 Eucalyptus sp Species 0.000 description 1
- 235000006914 Eucalyptus sp Nutrition 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 240000009088 Fragaria x ananassa Species 0.000 description 1
- 241001536358 Fraxinus Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 239000005562 Glyphosate Substances 0.000 description 1
- 229910003767 Gold(III) bromide Inorganic materials 0.000 description 1
- 229910003803 Gold(III) chloride Inorganic materials 0.000 description 1
- 239000007821 HATU Substances 0.000 description 1
- 241000208818 Helianthus Species 0.000 description 1
- 235000003222 Helianthus annuus Nutrition 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 235000008694 Humulus lupulus Nutrition 0.000 description 1
- 241000243251 Hydra Species 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 1
- 240000008415 Lactuca sativa Species 0.000 description 1
- 241000218195 Lauraceae Species 0.000 description 1
- 240000004322 Lens culinaris Species 0.000 description 1
- 235000014647 Lens culinaris subsp culinaris Nutrition 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 235000011430 Malus pumila Nutrition 0.000 description 1
- 235000015103 Malus silvestris Nutrition 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- 241000218231 Moraceae Species 0.000 description 1
- 235000008708 Morus alba Nutrition 0.000 description 1
- 240000005561 Musa balbisiana Species 0.000 description 1
- 231100000678 Mycotoxin Toxicity 0.000 description 1
- MMUOXEKRGPMSNR-UHFFFAOYSA-N O1NCCC=CC1 Chemical compound O1NCCC=CC1 MMUOXEKRGPMSNR-UHFFFAOYSA-N 0.000 description 1
- 241000207836 Olea <angiosperm> Species 0.000 description 1
- 240000001090 Papaver somniferum Species 0.000 description 1
- 235000008753 Papaver somniferum Nutrition 0.000 description 1
- 244000025272 Persea americana Species 0.000 description 1
- 235000008673 Persea americana Nutrition 0.000 description 1
- 241000218657 Picea Species 0.000 description 1
- 235000012570 Pinus sp Nutrition 0.000 description 1
- 241000758706 Piperaceae Species 0.000 description 1
- 235000010582 Pisum sativum Nutrition 0.000 description 1
- 240000004713 Pisum sativum Species 0.000 description 1
- 241000209466 Platanus Species 0.000 description 1
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 1
- 102000001253 Protein Kinase Human genes 0.000 description 1
- 240000005809 Prunus persica Species 0.000 description 1
- 235000006040 Prunus persica var persica Nutrition 0.000 description 1
- 235000014443 Pyrus communis Nutrition 0.000 description 1
- 240000000528 Ricinus communis Species 0.000 description 1
- 235000004443 Ricinus communis Nutrition 0.000 description 1
- 240000007651 Rubus glaucus Species 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 235000002597 Solanum melongena Nutrition 0.000 description 1
- 244000062793 Sorghum vulgare Species 0.000 description 1
- 235000009337 Spinacia oleracea Nutrition 0.000 description 1
- 244000300264 Spinacia oleracea Species 0.000 description 1
- 229930182692 Strobilurin Natural products 0.000 description 1
- 102000019259 Succinate Dehydrogenase Human genes 0.000 description 1
- 108010012901 Succinate Dehydrogenase Proteins 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 108010043934 Sucrose synthase Proteins 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 235000009470 Theobroma cacao Nutrition 0.000 description 1
- 241000921324 Tilia sp. Species 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical group [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 244000098345 Triticum durum Species 0.000 description 1
- 235000007264 Triticum durum Nutrition 0.000 description 1
- 240000003021 Tsuga heterophylla Species 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- 244000078534 Vaccinium myrtillus Species 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 241000219094 Vitaceae Species 0.000 description 1
- 229930003451 Vitamin B1 Natural products 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical group [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- JEDZLBFUGJTJGQ-UHFFFAOYSA-N [Na].COCCO[AlH]OCCOC Chemical compound [Na].COCCO[AlH]OCCOC JEDZLBFUGJTJGQ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- CWCGGQPNTDOHBA-UHFFFAOYSA-N acetonitrile;ruthenium Chemical compound [Ru].CC#N CWCGGQPNTDOHBA-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000012868 active agrochemical ingredient Substances 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 125000003670 adamantan-2-yl group Chemical group [H]C1([H])C(C2([H])[H])([H])C([H])([H])C3([H])C([*])([H])C1([H])C([H])([H])C2([H])C3([H])[H] 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 125000001980 alanyl group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000005108 alkenylthio group Chemical group 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- 125000002355 alkine group Chemical group 0.000 description 1
- 125000005103 alkyl silyl group Chemical group 0.000 description 1
- 125000005133 alkynyloxy group Chemical group 0.000 description 1
- 125000005109 alkynylthio group Chemical group 0.000 description 1
- 235000020224 almond Nutrition 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 description 1
- 235000019289 ammonium phosphates Nutrition 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 230000002180 anti-stress Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 1
- 235000021016 apples Nutrition 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 125000005018 aryl alkenyl group Chemical group 0.000 description 1
- 125000005104 aryl silyl group Chemical group 0.000 description 1
- NGLMYMJASOJOJY-UHFFFAOYSA-O azanium;calcium;nitrate Chemical compound [NH4+].[Ca].[O-][N+]([O-])=O NGLMYMJASOJOJY-UHFFFAOYSA-O 0.000 description 1
- 125000002785 azepinyl group Chemical group 0.000 description 1
- 235000021015 bananas Nutrition 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
- 235000021029 blackberry Nutrition 0.000 description 1
- 125000000707 boryl group Chemical group B* 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- WXMZPPIDLJRXNK-UHFFFAOYSA-N butyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(CCCC)C1=CC=CC=C1 WXMZPPIDLJRXNK-UHFFFAOYSA-N 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- 239000001511 capsicum annuum Substances 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 235000019693 cherries Nutrition 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 235000016213 coffee Nutrition 0.000 description 1
- 235000013353 coffee beverage Nutrition 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000001955 cumulated effect Effects 0.000 description 1
- 125000004465 cycloalkenyloxy group Chemical group 0.000 description 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 1
- 125000005357 cycloalkylalkynyl group Chemical group 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
- PYRZPBDTPRQYKG-UHFFFAOYSA-N cyclopentene-1-carboxylic acid Chemical compound OC(=O)C1=CCCC1 PYRZPBDTPRQYKG-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000008260 defense mechanism Effects 0.000 description 1
- 238000001784 detoxification Methods 0.000 description 1
- YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical compound Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 description 1
- 235000019621 digestibility Nutrition 0.000 description 1
- USKWPFJFWKHYJF-UHFFFAOYSA-L diiodoindium Chemical compound I[In]I USKWPFJFWKHYJF-UHFFFAOYSA-L 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000005712 elicitor Substances 0.000 description 1
- 230000013020 embryo development Effects 0.000 description 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- UPYTVYCVMAYLQD-UHFFFAOYSA-N ethyl 2-hydroxy-1,3-dimethyl-2-[2-(3-propan-2-ylphenyl)ethynyl]cyclohexane-1-carboxylate Chemical compound CCOC(=O)C1(C)CCCC(C)C1(O)C#CC1=CC=CC(C(C)C)=C1 UPYTVYCVMAYLQD-UHFFFAOYSA-N 0.000 description 1
- JHZPNBKZPAWCJD-UHFFFAOYSA-N ethyl 2-oxocyclopentane-1-carboxylate Chemical compound CCOC(=O)C1CCCC1=O JHZPNBKZPAWCJD-UHFFFAOYSA-N 0.000 description 1
- YSPVHAUJXLGZHP-UHFFFAOYSA-N ethyl piperidine-1-carboxylate Chemical compound CCOC(=O)N1CCCCC1 YSPVHAUJXLGZHP-UHFFFAOYSA-N 0.000 description 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 230000004883 flower formation Effects 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 1
- 229940097068 glyphosate Drugs 0.000 description 1
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- OVWPJGBVJCTEBJ-UHFFFAOYSA-K gold tribromide Chemical compound Br[Au](Br)Br OVWPJGBVJCTEBJ-UHFFFAOYSA-K 0.000 description 1
- RJHLTVSLYWWTEF-UHFFFAOYSA-K gold trichloride Chemical compound Cl[Au](Cl)Cl RJHLTVSLYWWTEF-UHFFFAOYSA-K 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 235000021021 grapes Nutrition 0.000 description 1
- 229910052735 hafnium Inorganic materials 0.000 description 1
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical group [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 150000002390 heteroarenes Chemical class 0.000 description 1
- 125000005312 heteroarylalkynyl group Chemical group 0.000 description 1
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 description 1
- 125000005844 heterocyclyloxy group Chemical group 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 description 1
- 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 description 1
- 125000000336 imidazol-5-yl group Chemical group [H]N1C([H])=NC([H])=C1[*] 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 150000002471 indium Chemical class 0.000 description 1
- 125000000593 indol-1-yl group Chemical group [H]C1=C([H])C([H])=C2N([*])C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 description 1
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 description 1
- 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 230000037427 ion transport Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 description 1
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 1
- 125000006262 isopropyl amino sulfonyl group Chemical group 0.000 description 1
- 125000004254 isoquinolin-1-yl group Chemical group [H]C1=C([H])C2=C([H])C([H])=C([H])C([H])=C2C(*)=N1 0.000 description 1
- 125000004551 isoquinolin-3-yl group Chemical group C1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 125000004552 isoquinolin-4-yl group Chemical group C1=NC=C(C2=CC=CC=C12)* 0.000 description 1
- 125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000001793 isothiazol-3-yl group Chemical group [H]C1=C([H])C(*)=NS1 0.000 description 1
- 125000004501 isothiazol-5-yl group Chemical group S1N=CC=C1* 0.000 description 1
- 125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 description 1
- 125000004498 isoxazol-4-yl group Chemical group O1N=CC(=C1)* 0.000 description 1
- 125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 description 1
- ZNJFBWYDHIGLCU-UHFFFAOYSA-N jasmonic acid Natural products CCC=CCC1C(CC(O)=O)CCC1=O ZNJFBWYDHIGLCU-UHFFFAOYSA-N 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- WABPQHHGFIMREM-UHFFFAOYSA-N lead(0) Chemical group [Pb] WABPQHHGFIMREM-UHFFFAOYSA-N 0.000 description 1
- 235000021374 legumes Nutrition 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical group [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 125000006261 methyl amino sulfonyl group Chemical group [H]N(C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 239000011785 micronutrient Substances 0.000 description 1
- 235000013369 micronutrients Nutrition 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000009456 molecular mechanism Effects 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- 239000002636 mycotoxin Substances 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- APVPOHHVBBYQAV-UHFFFAOYSA-N n-(4-aminophenyl)sulfonyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 APVPOHHVBBYQAV-UHFFFAOYSA-N 0.000 description 1
- IDEHCMNLNCJQST-UHFFFAOYSA-N n-(6-aminohexyl)-5-chloro-1-naphthalenesulfonamide Chemical compound C1=CC=C2C(S(=O)(=O)NCCCCCCN)=CC=CC2=C1Cl IDEHCMNLNCJQST-UHFFFAOYSA-N 0.000 description 1
- 125000006126 n-butyl sulfonyl group Chemical group 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000006124 n-propyl sulfonyl group Chemical group 0.000 description 1
- ZFIFHAKCBWOSRN-UHFFFAOYSA-N naphthalene-1-sulfonamide Chemical compound C1=CC=C2C(S(=O)(=O)N)=CC=CC2=C1 ZFIFHAKCBWOSRN-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000005146 naphthylsulfonyl group Chemical group C1(=CC=CC2=CC=CC=C12)S(=O)(=O)* 0.000 description 1
- 239000000618 nitrogen fertilizer Substances 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 235000014571 nuts Nutrition 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000003585 oxepinyl group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000036542 oxidative stress Effects 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 235000021017 pears Nutrition 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 229940112042 peripherally acting choline derivative muscle relaxants Drugs 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- 230000006461 physiological response Effects 0.000 description 1
- 229930195732 phytohormone Natural products 0.000 description 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
- 235000021018 plums Nutrition 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 230000010152 pollination Effects 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 125000006684 polyhaloalkyl group Polymers 0.000 description 1
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 108010007439 proline transporter Proteins 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 108060006633 protein kinase Proteins 0.000 description 1
- 150000003195 pteridines Chemical class 0.000 description 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
- YEYHFKBVNARCNE-UHFFFAOYSA-N pyrido[2,3-b]pyrazine Chemical compound N1=CC=NC2=CC=CN=C21 YEYHFKBVNARCNE-UHFFFAOYSA-N 0.000 description 1
- OHZYAOYVLLHTGW-UHFFFAOYSA-N pyrido[3,2-c]pyridazine Chemical compound C1=CN=NC2=CC=CN=C21 OHZYAOYVLLHTGW-UHFFFAOYSA-N 0.000 description 1
- 150000008518 pyridopyrimidines Chemical class 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- JOZPEVMCAKXSEY-UHFFFAOYSA-N pyrimido[5,4-d]pyrimidine Chemical compound N1=CN=CC2=NC=NC=C21 JOZPEVMCAKXSEY-UHFFFAOYSA-N 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 125000004159 quinolin-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C([H])C(*)=NC2=C1[H] 0.000 description 1
- 125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 description 1
- 125000004549 quinolin-4-yl group Chemical group N1=CC=C(C2=CC=CC=C12)* 0.000 description 1
- 125000004550 quinolin-6-yl group Chemical group N1=CC=CC2=CC(=CC=C12)* 0.000 description 1
- 235000021013 raspberries Nutrition 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000006808 response to salt stress Effects 0.000 description 1
- 230000021749 root development Effects 0.000 description 1
- 230000002786 root growth Effects 0.000 description 1
- 235000012045 salad Nutrition 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 125000005930 sec-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- 230000011664 signaling Effects 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- BABPEPRNSRIYFA-UHFFFAOYSA-N silyl trifluoromethanesulfonate Chemical compound FC(F)(F)S(=O)(=O)O[SiH3] BABPEPRNSRIYFA-UHFFFAOYSA-N 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000012419 sodium bis(2-methoxyethoxy)aluminum hydride Substances 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229940080262 sodium tetrachloroaurate Drugs 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 235000020354 squash Nutrition 0.000 description 1
- 125000003638 stannyl group Chemical group [H][Sn]([H])([H])* 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 235000021012 strawberries Nutrition 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229940065721 systemic for obstructive airway disease xanthines Drugs 0.000 description 1
- 235000013616 tea Nutrition 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 229960003495 thiamine Drugs 0.000 description 1
- DPJRMOMPQZCRJU-UHFFFAOYSA-M thiamine hydrochloride Chemical compound Cl.[Cl-].CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N DPJRMOMPQZCRJU-UHFFFAOYSA-M 0.000 description 1
- 125000003777 thiepinyl group Chemical group 0.000 description 1
- 125000001730 thiiranyl group Chemical group 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 125000000464 thioxo group Chemical group S=* 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 125000005208 trialkylammonium group Chemical group 0.000 description 1
- KKEOZWYTZSNYLJ-UHFFFAOYSA-O triazanium;nitrate;sulfate Chemical compound [NH4+].[NH4+].[NH4+].[O-][N+]([O-])=O.[O-]S([O-])(=O)=O KKEOZWYTZSNYLJ-UHFFFAOYSA-O 0.000 description 1
- YFSQOQQWMKPPMF-UHFFFAOYSA-N triethylsilyl methanesulfonate Chemical compound CC[Si](CC)(CC)OS(C)(=O)=O YFSQOQQWMKPPMF-UHFFFAOYSA-N 0.000 description 1
- STMPXDBGVJZCEX-UHFFFAOYSA-N triethylsilyl trifluoromethanesulfonate Chemical compound CC[Si](CC)(CC)OS(=O)(=O)C(F)(F)F STMPXDBGVJZCEX-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 239000011691 vitamin B1 Substances 0.000 description 1
- 235000010374 vitamin B1 Nutrition 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/06—Oxygen or sulfur directly attached to a cycloaliphatic ring system
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
- A01N31/14—Ethers
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-oxygen bonds
- A01N33/24—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-oxygen bonds only one oxygen atom attached to the nitrogen atom
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen
- A01N35/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen containing a carbon-to-nitrogen double bond
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/20—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom three- or four-membered rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
Definitions
- the invention relates to the use of substituted 1 - (arylethynyl) -, 1 -
- Germination inhibitors are described in US2010 / 0160166. It is also known that (2Z, 4E) -5 - [(1S, 6S) -1-hydroxy-2,2,6-trimethylcyclohexyl] penta-2,4-dienoic acid and (2Z, 4E) -5- [(1R.6R) -1 -Hydroxy-2,2,6-trimethylcyclohexyl] penta-2,4-dienoic acid interact with cytochrome P707A (see Current Med. Chem., 2010, 17, 3230).
- substituted l- (arylethynyl) -, 1- (heteroarylethynyl) -, 1- (heterocyclylethynyl) - and 1- (cycloalkenylethynyl) -cyclohexanols represent the use for increasing the stress tolerance in plants to abiotic stress, for strengthening plant growth and / or to increase the
- the signal chain genes of the abiotic stress reaction include transcription factors of the classes DREB and CBF (Jaglo-Ottosen et al., 1998, Science 280; 104-106).
- the response to salt stress involves phosphatases of the ATPK and MP2C types.
- salt stress the biosynthesis of osmolytes such as proline or sucrose is often activated.
- sucrose Synthase and proline transporters Hasegawa et al., 2000, Annu Rev Plant Physiol Plant Mol Biol 51: 463-499.
- Late Embryogenesis Abundant Proteins which include dehydrins as an important class, is known (Ingram and Bartels, 1996, Annu Rev Plant Physiol Plant Mol Biol 47: 277-403, Close, 1997, Physiol Plant 100: 291-296). These are chaperones that stabilize vesicles, proteins and membrane structures in stressed plants (Bray, 1993, Plant Physiol 103: 1035-1040). Moreover, induction of aldehyde dehydrogenases, which detoxify the reactive oxygen species (ROS) produced by oxidative stress, is often used (Kirch et al., 2005, Plant Mol Biol 57: 315-332).
- ROS reactive oxygen species
- HSF Heat Shock Factors
- HSP Heat Shock Proteins
- Substances or their stable synthetic derivatives and derived structures are also effective in external application to plants or seed dressing and activate defense reactions that result in an increased stress or pathogen tolerance of the plant [Sembdner, and Parthier, 1993, Ann. Rev. Plant Physiol. Plant Mol. Biol. 44: 569-589].
- osmolytes e.g. Glycine betaine or its biochemical precursors, e.g. Choline derivatives
- PARP poly-ADP-ribose polymerases
- PARG poly (ADP-ribose) glycohydrolases
- the object of the present invention was to provide further compounds which increase the tolerance to abiotic stress in plants, in particular to effect a strengthening of plant growth and / or contribute to increasing the plant yield.
- the present invention accordingly provides the use of substituted 1 - (arylethynyl) -, 1 - (heteroarylethynyl) -, l - (heterocyclylethynyl) - and 1 - (cycloalkenylethynyl) - cyclohexanols of the general formula (I) or salts thereof for increasing the
- R 17 , R 18 , R 19 , R 20 , R 22 , R 23 , R 24 , R 25 , R 26 , R 28 , R 29 and R 30 and A 1 to A 9 each have the meaning as defined below, and wherein the arrow represents a bond to the respective grouping CR 6 in the general formula (I),
- R 1 is alkyl, cycioalkyl, cycloalkenyl, alkenyl, alkynyl, alkenylalkyl, alkynylalkyl, aikoxyalkyl, hydroxyalkyl, haloalkyl, haloalkyl, haloalkynyl, haloalkoxyalkyl, alkoxyhaloalkyl, haloalkoxyhaloalkyl, alkylthioalkyl, haloalkylthioalkyl, aryl, heteroaryl, heterocyclyl,
- R 2 , R 3 and R 4 independently of one another are hydrogen, halogen, alkyl, cycioalkyl, cycloalkenyl, alkenyl, alkynyl, alkenylalkyl, alkynylalkyl, aikoxyalkyi,
- R 5 is hydroxy, alkoxy, aryloxy, cycloalkyloxy, alkenyloxy, alkenylalkyloxy,
- Trialkylsilylalkoxyalkyloxy for nitro, amino, hydroxy, hydrothio, thiocyanato, isothiocyanato, halogen, alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, arylalkynyl, trialkylsilylalkynyl, aryl, arylalkyl, arylalkoxy, heteroaryl, haloalkyl, halocycloalkyl, haloalkenyl, alkoxy, haloalkoxy, aryloxy, heteroaryloxy , Cycloalkyloxy, cycloalkylalkoxy, alkenyloxy, alkynylalkyloxy, hydroxyalkyl, alkoxyalkyl, aryloxyalkyl,
- Haloalkylcarbonylamino alkoxycarbonylamino, alkylaminocarbonylamino, alkyl (alkyl) aminocarbonylamino, alkylsulfonylamino, cycloalkylsulfonylamino, arylsulfonylamino, hetarylsulfonylamino, sulfonylhaloalkylamino,
- Amino-alkylsulfonyl amino-halo-alkylsulfonyl, alkylaminosulfonyl, aminosulfonyl, bisalkylaminosulfonyl, cycloalkylaminosulfonyl, haloalkylaminosulfonyl, heteroarylaminosulfonyl, arylaminosulfonyl, arylalkylaminosulfonyl,
- Alkoxyalkoxycarbonyl alkenyloxyalkoxycarbonyl, alkylaminoalkoxycarbonyl, trisalkylsilyloxyalkoxycarbonyl, bis-alkylaminoalkoxycarbonyl,
- Heterocyclylalkoxycarbonyl heterocyclyloxycarbonyl, alkenylalkoxycarbonyl, alkynylalkoxycarbonyl, arylalkynyloxycarbonyl, arylalkenyloxycarbonyl,
- Aminocarbonyl alkylaminocarbonyl, bisalkylaminocarbonyl,
- Alkoxyalkylaminocarbonyl alkenylaminocarbonyl, cycloalkylaminocarbonyl, Arylaminocarbonyl, arylalkylaminocarbonyl, heteroarylalkylaminocarbonyl, cyanoalkylaminocarbonyl, haloalkylaminocarbonyl, alkynylalkylaminocarbonyl, alkoxycarbonylaminocarbonyl, arylalkoxycarbonylaminocarbonyl,
- Alkylaminocarbonylalkyl aminocarbonylalkyl, bisalkylaminocarbonylalkyl, cycloalkylaminocarbonylalkyl, arylalkylaminocarbonylalkyl,
- Alkoxycarbonylalkyl (alkyl) aminocarbonyl
- Aminocarbonylalkylaminocarbonyl alkylaminocarbonylalkylaminocarbonyl, cycloalkylaminocarbonylalkylaminocarbonyl, cycloalkylalkylaminocarbonyl, cycloalkylalkylaminocarbonylalkyl,
- Alkoxycarbonylheterocyclyl alkenyloxycarbonylheterocyclyl,
- Arylalkylaminocarbonylheterocyclyl alkenylaminocarbonylheterocyclyl, Hydroxycarbonylheterocyclylalkyl, alkoxycarbonylheterocyclylalkyl,
- R 7 , R 8 , R 9 and R 10 are each independently hydrogen, halogen, nitro, amino, cyano, alkyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl, alkenyl, alkynyl, alkenylalkyl, alkynylalkyl, hydroxy, alkoxy, alkoxyalkoxy, alkoxyalkyl,
- Haloalkylcarbonylamino alkoxycarbonylamino, alkylaminocarbonylamino, (alkyl) aminocarbonylamino, alkylsulfonylamino, cycloalkylsulfonylamino, arylsulfonylamino, hetarylsulfonylamino, sulfonylhaloalkylamino,
- Aminoalkylsulfonyl aminohaloalkylsulfonyl, alkylaminosulfonyl,
- Arylalkoxycarbonyl alkenyloxycarbonyl, alkynyloxycarbonyl, aminocarbonyl, alkylaminocarbonyl, bisalkylaminocarbonyl, alkyl (alkyl) aminocarbonyl,
- a 1 , A 2 , A 3 and A 4 are the same or different and are independently N
- R 11 and R 12 independently of one another represent hydrogen, halogen, alkyl, aryl, heteroaryl, heterocyclyl, cycloalkyl, alkenyl, alkynyl, alkoxy, alkoxyalkyl, aryloxyalkyl, Haloalkoxy, haloalkyl, haloalkoxyalkyl, alkoxyhaloalkyl, haloalkoxyhaloalkyl, alkylthio, haloalkylthio, alkylthioalkyl, hydroxycarbonyl, alkoxycarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, aryloxycarbonyl,
- Arylalkoxycarbonyl alkenyloxycarbonyl, alkynyloxycarbonyl, aminocarbonyl, alkylaminocarbonyl, bisalkylaminocarbonyl, alkyl (alkyl) aminocarbonyl,
- R 13 , R 14 , R 17 and R 8 independently of one another represent hydrogen, alkyl, halogen,
- R 13 and R 17 with the atoms to which they are attached form a fully saturated or partially saturated, optionally further substituted 5 to 7-membered ring.
- R 15 and R 16 in the group CR 15 R 16 each have the same or different meanings as defined below, and R 15 and R 16 independently of one another are hydrogen, halogen, alkyl, aryl, heteroaryl, heterocyclyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl, aryloxyalkyl, haloalkoxy, haloalkyl, haloalkoxyalkyl, alkoxyhaloalkyl, haloalkoxyhaloalkyl, alkyoxyhaloalkyl, haloalkoxyhaloalkyl, alkylthio, haloalkylthio, alkylthioalkyl, hydroxycarbonyl, alkoxycarbonyl,
- Arylalkoxycarbonyl alkenyloxycarbonyl, alkynyloxycarbonyl, aminocarbonyl, alkylaminocarbonyl, bisalkylaminocarbonyl, alkyl (alkyl) aminocarbonyl, alkyl (alkoxy) aminocarbonyl, alkenylaminocarbonyl, cycloalkylaminocarbonyl, arylaminocarbonyl, arylalkylaminocarbonyl, amino, alkylamino,
- Cycloalkylamino bis-alkylamino, arylthio, cycloalkylthio, heterocyclylthio,
- Cycloalkylsuifonyl, Heterocyclyisulfonyl, R 19 , R 20 , R 22 and R 23 are each independently hydrogen, alkyl, halogen,
- Heterocyclylalkyl alkoxy, alkoxyalkoxy, alkoxyalkyl, haloalkyl, alkylthio, arylthio, cycloalkylthio, heterocyclylthio, alkylsulfinyl, arylsulfinyl,
- Heteroarylsulfinyl cycloalkylsulfinyl, heterocyclylsulfinyl, alkylsulfonyl,
- R 21 is hydrogen, halogen, alkyl, aryl, heteroaryl, heterocyclyl, cycloalkyl, alkenyl, alkynyl, heterocyclylalkyl, alkoxy, alkoxyalkyl, aryloxyalkyl, haloalkoxy, haloalkyl, alkoxyhaloalkyl, haloalkoxyhaloalkyl, alkylthio, haloalkylthio, alkylthioalkyl, hydroxycarbonyl, alkoxycarbonyl, cycloalkoxycarbonyl,
- Arylalkoxycarbonyl alkenyloxycarbonyl, alkynyloxycarbonyl, aminocarbonyl,
- Alkylaminocarbonyl bisalkylaminocarbonyl, alkyl (alkyl) aminocarbonyl, alkyl (alkoxy) aminocarbonyl, alkenylaminocarbonyl, cycloalkylaminocarbonyl, arylaminocarbonyl, arylalkylaminocarbonyl, amino, alkylamino,
- Cycloalkylamino bis-alkylamino, arylthio, cycloalkylthio, heterocyclylthio, Alkylsulfinyl, arylsulfinyl, heteroarylsulfinyl, cycloalkylsulfinyl, heterocyclylsulfinyl, alkylsulfonyl, arylsulfonyl, heteroarylsulfonyl,
- R 24 , R 25 , R 26 , R 28 , R 29 and R 30 are each independently hydrogen, alkyl
- Halogen cycloalkyl, aryl, heteroaryl, heterocyclyl, alkenyl, alkoxy,
- R 27 is hydrogen, halogen, alkyl, aryl, heteroaryl, heterocyclyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl, aryloxyalkyl, haloalkoxy, haloalkyl, alkylthio, haloalkylthio, hydroxycarbonyl, alkoxycarbonyl, cycloalkoxycarbonyl, arylalkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, aminocarbonyl, alkylaminocarbonyl, Bisalkylaminocarbonyl, alkyl (alkyl) aminocarbonyl, alkyl (alkoxy) aminocarbonyl, alkenylaminocarbonyl, cycloalkylaminocarbonyl, arylaminocarbonyl,
- Arylalkylaminocarbonyl amino, alkylamino, cycloalkylamino, bis-alkylamino, arylthio, cycloalkylthio, heterocyclylthio, alkylsulfinyl, arylsulfinyl,
- Heteroarylsulfinyl cycloalkylsulfinyl, heterocyclylsulfinyl, alkylsulfonyl,
- the compounds of general formula (I) may be prepared by addition of a suitable inorganic or organic acid such as, for example, mineral acids such as HCl, HBr, H 2 SO 4, H 3 PO 4 or HNO 3, or organic acids, e.g.
- a suitable inorganic or organic acid such as, for example, mineral acids such as HCl, HBr, H 2 SO 4, H 3 PO 4 or HNO 3, or organic acids, e.g.
- carboxylic acids such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid or sulfonic acids such as p-toluenesulfonic acid to form a basic group such as amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino, salts.
- These salts then contain the conjugate base of the acid as an anion.
- R 7 , R 8 , R 9 , R 1Ü , R 11 , R 12 , R 13 , R 14 , R 17 , R 18 , R 19 , R 20 , R 22 , R 23 , R 24 , R 25 , R 26 , R 28 , R 29 and R 30 and A 1 to A 9 are each as defined below, and wherein the arrow indicates a bond to the respective grouping CR 6 in the general formula (I), R 1 is (Ci-Cs) alkyl, (C 3 -C 8) cycloalkyl, (C 4 -C 8) cycloalkenyl, (C2-C8) alkenyl, (C 2 -C 8) alkynyl, (C 2 -C 8) alkenyl (-C 8) alkyl, (C 2 -C 8) alkynyl (Ci-C 8) alkyl, (Ci-C 8) alkoxy (CrC 8)
- R 2 , R 3 and R 4 independently of one another represent hydrogen, halogen, (C 1 -C 5) -alkyl,
- R 5 is hydroxy, (CRCs) alkoxy, Aryioxy, (C3-C8) cycloalkyloxy, (C 2 -C 8) alkenyloxy, (C 2 -C 8) alkenyl (Ci-C8) alkyloxy , (Ci-C 8) alkoxy (Ci-C8) alkyloxy, (Ci-C 8) - alkylcarbonyloxy, arylcarbonyloxy, heteroarylcarbonyloxy, (C3-C8) - cycloalkylcarbonyloxy, (Ci-C 8) alkoxycarbonyloxy, (C 2 -C 8) - Alkenyloxycarbonyloxy, aryloxy (Ci-C8) alkyloxy, aryl (Ci-C8) alkyloxy, (dC 8) - alkoxy (Ci-C 8) alkoxy (C -C 8) -alkyloxy, (Ci-C8) alkylthio
- R 6 for nitro, amino, hydroxy, hydrothio, thiocyanato, isothiocyanato, halogen
- R 7, R 8, R 9 and R 10 are independently hydrogen, halogen, nitro, amino, cyano, (CrC 8) alkyl, aryl, heteroaryl, (C 3 -C 8) cycloalkyl, (C 4 -C 8) -cycloalkenyl, (C 2 -C 8) alkenyl, (C 2 -C 8) -alkynyl, (C2-C8) alkenyl (Ci-C 8) alkyl, (C 2 -C 8) Alkynyl (C 1 -C 8 ) -alkyl, hydroxy, (C 1 -C 8 ) -alkoxy, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkoxy, (d-Ce) -alkoxy- Ci-C 8) alkyl, hydroxy (Ci-C 8) alkyl, (Ci-C8) -haloalkoxy, (Ci-C
- a 1 , A 2 , A 3 and A 4 are the same or different and are independently N
- R 11 and R 12 independently of one another represent hydrogen, halogen, (C 1 -C 5 ) -alkyl, aryl, heteroaryl, heterocyclyl, (C 3 -C 8 ) -cycloalkyl, (C 2 -C 8 ) -alkenyl, (C 2 - C 8 ) -alkynyl, (C 1 -C 8 ) -alkoxy, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, aryloxy- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkoxy , (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) -haloalkoxy- (C 1 -C 8 )
- R 14 , R 17 and R 18 independently of one another represent hydrogen, (C 1 -C 8 ) -alkyl, halogen, (C 3 -C 8 ) -cycloalkyl, aryl, heteroaryl, heterocyclyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8) - alkenyl (-C 8) alkyl, aryl (Ci-C8) alkyl, (dC 8) alkoxy, (Ci-C 8) alkoxy (Ci-C 8) - alkoxy, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, hydroxy, (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) -haloalkylthio or and R 17 having the atoms to which they are attached, form a fully saturated or partially saturated, optionally further substituted 5 to 7-membered
- R 15 and R 16 are independently hydrogen, halogen, (CRCs) alkyl, aryl, heteroaryl, heterocyclyl, (C 3 -C 8) cycloalkyl, (C2-C8) alkenyl, (Ci-C 8) - alkoxy, (Ci-C 8) alkoxy (CrC 8) alkyl, aryloxy (dC 8) alkyl, (dC 8) -haloalkoxy, (dC 8) - haloalkyl, (Ci-C8) haloalkoxy ( CrC 8 ) alkyl.
- a 8 is O (oxygen), S (sulfur), NH, N-CH 3 , N-OCH 3 or the moiety CHR 21 , and wherein R 21 in the moiety CHR 21 has the meaning as defined below,
- R 21 is hydrogen, halogen, (DC 8) alkyl, aryl, heteroaryl, heterocyclyl, (C; iC 8) - cycloalkyl, (C 2 -C 8) alkenyl, (Ci-Cs) alkoxy, (CrC 8 ) alkoxy (Ci-C 8) alkyl, aryloxy (Ci-C8) alkyl, (Ci-Cs) haloalkoxy, (dC 8) -haloalkyl, (dC 8) alkoxy- (Ci-Cs ) -haloalkyl, (C 1 -C 8 ) -haloalkoxy- (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) -alkylthio,
- (Ci-C 8) alkylaminocarbonyl bis [(Ci-C 8) alkyl] aminocarbonyl, (Ci-C 8) - alkyl [(Ci-C 8) alkyl] aminocarbonyl, (Ci-C 8) -alkyl [(C 1 -C 8 ) -alkoxy] aminocarbonyl, (C 2 -C 8 ) -alkenylaminocarbonyl, (C 3 -C 8 ) -cycloalkylaminocarbonyl,
- R 24, R 25, R 26, R 28, R 29 and R 30 are independently hydrogen, (Ci-C 8) alkyl, halogen, (C 3 -C 8) cycloalkyl, aryl, heteroaryl, heterocyclyl, ( C 2 -C 8 -alkenyl, (C 1 -C 5) -alkoxy, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkoxy, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) - alkyl, (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) -alkylthio, (C 1 -C 8 ) -haloalkylthio,
- a 9 is O (oxygen), S (sulfur), NH, N-CH 3, N -OCH 3 or the moiety CHR 27 and wherein R 27 in the moiety CHR 27 has the meaning as defined below and
- R 27 is hydrogen, halogen, (Ci-C 8) alkyl, aryl, heteroaryl, heterocyclyl, (C 3 -C 8) - cycloalkyl, (C 2 -C 8) alkenyl, (DC 8) alkoxy, ( C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, Aryloxy- (Ci-C 8 ) -alkyl, (Ci-C 8 ) -haloalkoxy, (Ci-C 8 ) -haloalkyl, (Ci-Ce) -alkylthio, (d-CsJ-haloalkylthio, hydroxycarbonyl, (Ci-C8 ) Alkoxycarbonyl, (Ca-Ce) - cycloalkoxycarbonyl, aryl- (C 1 -C 8) -alkoxycarbonyl, (C 2 -C 8) -alken
- R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 17 , R 18 , R 19 , R 20 , R 22 , R 23 , R 24 , R 25 , R 26 , R 28 , R 29 and R 30 and A 1 to A 9 are each as defined in the have the following definitions and wherein the arrow for a bond to the respective grouping is CR 6 in the general formula (I),
- R 1 is (C 1 -C 7 ) -alkyl, (C 3 -C 7 ) -cycloalkyl, (C 4 -C 7 ) -cycloalkenyl, (C 2 -C 7 ) -alkenyl, (C 2 -C 7 ) - alkynyl, (C 2 -C 7) (alkenyl (Ci-C7) alkyl, (C 2 -C 7) alkynyl (Ci-C7) alkyl, (Ci-C7) alkoxy Ci-C 7) alkyl, hydroxy (Ci-C7) alkyl, (Ci-C7) haloalkyl, (C2-C7) - haloalkenyl, (C 2 -C 7) haloalkynyl, (Ci-C 7 ) haloalkoxy- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkoxy- (C
- R 2 , R 3 and R 4 independently of one another represent hydrogen, halogen, (C 1 -C 7 ) -alkyl,
- R 5 is hydroxy, (Ci-C7) alkoxy, aryloxy, (C3-C7) cycloalkyloxy, (C 2 -C 7) alkenyloxy, (C 2 -C 7) alkenyl (Ci-C 7 ) -alkyloxy, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyloxy, (C 1 -C 7 ) -alkylcarbonyloxy, arylcarbonyloxy, heteroarylcarbonyloxy, (C 3 -C 7 ) -cycloalkylcarbonyloxy, (C 1 -C 7 ) -alkoxycarbonyloxy , (C2-C7) - Alkenyloxycarbonyloxy, aryloxy (dC 7) alkyloxy, aryl- (Ci-C7) alkyloxy, (C1-C7) - alkoxy (Ci-C7) alkoxy (Ci-C
- R 6 for nitro, amino, hydroxy, hydrothio, thiocyanato, isothiocyanato, halogen
- heteroaryloxycarbonyl heteroaryl- (C 1 -C 7 ) -alkoxycarbonyl, heterocyclyl- (C 1 -C 7 ) -alkoxycarbonyl, heterocyclyloxycarbonyl, (C 2 -C 7 ) -alkenyl- (C 1 -C 7 ) - alkoxycarbonyl, (C 2 -C 7) -alkynyl- (C 1 -C 7) -alkoxycarbonyl, aryl- (C-2-C-7) -alkynyloxycarbonyl, aryl- (C 2 -C 7) -alkenyloxycarbonyl, aminocarbonyl, (C 1 -C 7) - Alkylaminocarbonyl, bis [(Ci-C7) -alkyl] aminocarbonyl, (Ci-C7) -alkyl [(Ci-C7) - alkyljaminocarbonyl, (Ci-Ci-
- R 7, R 8, R 9 and R 10 are independently hydrogen, halogen, nitro, amino, cyano, (dC 7) alkyl, aryl, heteroaryl, (C 3 -C 7) -Cycloalkyi, (C 4 -C 7) cycloalkenyl, (C2-C7) alkenyl, (C2-C7) -Alkinyi, (C2-C7) alkenyl (Ci-C7) alkyl, (C 2 -C 7) alkynyl (Ci-C7) -alkyl, hydroxy, (Ci-C7) alkoxy, (Ci-C7) alkoxy (Ci-C7) alkoxy, (C1-C7) - Aikoxy- (Ci-C 7 ) alkyl, hydroxy (Ci-C7) alkyl, (Ci-C 7) -Haioaikoxy, (C1-C7) - Haloalkyi, (C 2 -C 7) hal
- a 1 , A 2 , A 3 and A 4 are the same or different and are independently N
- R 1 and R 12 independently of one another represent hydrogen, halogen, (C 1 -C 7 ) -alkyl, aryl, heteroaryl, heterocyclyl, (C 3 -C 7 ) -cycloalkyl, (C 2 -C 7 ) -alkenyl, (C 2 - C 7 ) -alkynyl, (C 1 -C 7 ) -alkoxy, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, aryloxy- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) - Haloalkoxy, (Ci-C 7 ) -haloalkyl, (Ci-C 7 ) -haloalkoxy- (Ci-C7) -alkyl, (Ci-C 7 ) -alkoxy- (Ci-C 7 ) -haloalkyl, (Ci-
- R 13, R 14, R 17 and R 18 are independently hydrogen, (Ci-C-7) alkyl, halogen, (C3-C 7) cycloalkyl, aryl, heteroaryl, heterocyclyl, (C 2 -C 7) Alkenyl, (C 2 -C 7 ) -alkenyl- (C 1 -C 7 ) -alkyl, aryl- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkoxy, (C 1 -C 7 ) -alkoxy- ( Ci-C 7 ) - alkoxy, (Ci-C7) -alkoxy- (Ci-C 7 ) -alkyl, hydroxy, (Ci-C 7 ) -haloalkyl, (C 1 -C 7 ) - haloalkylthio or
- R 13 and R 17 with the atoms to which they are attached form a completely saturated or partially saturated, optionally further substituted 5 to 7-membered ring,
- a 6 , A 7 are the same or different and independently of one another are O (oxygen), S (sulfur), NH, N-OCH 3, N-CH 3 or the group CR 15 R 16 , although in each case two N-, O or S atoms are adjacent, and wherein R 15 and R 16 in the group CR 15 R 16 are identical or different
- R 15 and R 16 independently of one another represent hydrogen, halogen, (C 1 -C 7 ) -alkyl, aryl, heteroaryl, heterocyclyl, (C 3 -C 7 ) -cycloalkyl, (C 2 -C 7 ) -alkenyl, (CrC 7 ) Alkoxy, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, aryloxy- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -haloalkoxy, (C 1 -C 7 ) -haloalkyl, C 7 ) -haloalkoxy (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -haloalkyl, (C 1 ) -
- R 19 , R 20 , R 22 and R 23 independently of one another represent hydrogen, (C 1 -C 7 ) -alkyl, halogen, (C 3 -C 7 ) -cycloalkyl, aryl, heteroaryl, heterocyclyl, (C 2 -C 7 ) - alkenyl, aryl (Ci-C7) - alkyl, (Ci-C7) alkoxy, (Ci-C7) alkoxy (Ci-C7) alkoxy, (Ci-C7) alkoxy ( Ci-C 7 ) - alkyl, (Ci-C 7 ) -haloalkyl,
- a 8 is O (oxygen), S (sulfur), NH, N-CH 3 , N-OCH 3 or the moiety CHR 21 , and wherein R 21 in the moiety CHR 21 has the meaning as defined below,
- R 21 is hydrogen, halogen, (C 1 -C 7 ) -alkyl, aryl, heteroaryl, heterocyclyl, (C 3 -C 7 ) -cycloalkyl, (C 2 -C 7 ) -alkenyl, (C 1 -C 7 ) -alkoxy, (Ci-C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, aryloxy- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -haloalkoxy, (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -alkoxy (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -haloalkoxy- (C 1 -C 7 ) -haloalkyl, (C 1
- (C 1 -C 7) -alkylaminocarbonyl bis [(C 1 -C 7) -alkyl] aminocarbonyl, (C 1 -C 7) -alkyl [(C 1 -C 7) -alkyl] aminocarbonyl, (C 1 -C 7) -alkyl [(C 1 -C 7) -alkoxy] aminocarbonyl, (C 2 -C 7) -alkenylaminocarbonyl, (C 3 -C 7) -cycloalkylaminocarbonyl,
- R 24 , R 25 , R 26 , R 28 , R 29 and R 30 independently of one another represent hydrogen, (C 1 -C 7 ) -alkyl, halogen, (C 3 -C 7 ) -cycloalkyl, aryl, heteroaryl, heterocyclyl, (C 2 -C 4 ) -cycloalkyl, C7) alkenyl, (C 1 -C 7 ) -alkoxy, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkoxy, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, (Ci -C 7) haloalkyl, (Ci-C7) -alkylthio, (Ci-C 7) are haloalkylthio,
- a 9 is O (oxygen), S (sulfur), NH, N-CH 3 , N -OCH 3 or the moiety CHR 27 and wherein R 27 in the moiety CHR 27 has the meaning as defined below and R 27 represents hydrogen, halogen, (C 1 -C 7 ) -alkyl, aryl, heteroaryl, heterocyclyl, (C 3 -C 7 ) -cycloalkyl, (C 2 -C 7 ) -alkenyl, (C 1 -C 7 ) -alkoxy, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, aryloxy- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -haloalkoxy, (C 1 -C 7 ) -haloalkyl, (C rC 7 ) -Alkylthio, (C 1 -C 7) -haloal
- R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 17 , R 18 , R 19 , R 20 , R 22 , R 23 , R 24 , R 25 , R 26 , R 28 , R 29 and R 30 and A 1 to A 9 each have the meaning according to the definitions below and wherein the arrow for a bond to the respective group CR 6 in the general formula (I),
- R 1 is (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, (C 4 -C 6 ) -cycloalkenyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl , (C 2 -C 6) alkenyl (Ci-C 6) alkyl, (C2-C6) alkynyl (Ci-C 6) alkyl, (Ci-C 6) alkoxy (Ci- C 6) alkyl, hydroxy (Ci-C 6) alkyl, (Ci-C 6) -haloalkyl, (C 2 -C 6) - haloalkenyl, (C 2 -C 6) haloalkynyl group,
- R 2 , R 3 and R 4 independently of one another represent hydrogen, fluorine, (C 1 -C 6) -alkyl, (Ca-Ce) -
- R 6 for nitro, amino, hydroxy, hydrothio, thiocyanato, isothiocyanato, fluorine, chlorine,
- Haloalkyl (C 3 -C 6) halocycloalkyl, (C 2 -C 6) haloalkenyl, (Ci-C 6) alkoxy, (Ci-C6) - haloalkoxy, aryloxy, heteroaryloxy, (C3-C6) - Cycloalkyloxy, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkoxy, (C 2 -C 6 ) - (C 2 -C 6 ) -alkenyloxy, (C 2 -C 6 ) -alkynyl- (C 2 -C 6 ) -alkyloxy, hydroxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, aryloxy- (C 1 -C 6 ) -alkyl, Heoaryl
- R 7 , R 8 , R 9 and R 10 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, nitro, amino, cyano, optionally substituted phenyl, heteroaryl, (C 3 -C 6 ) -cycloalkyl, (C 4 -C 6 ) -cycloalkenyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, (C 2 -C 6 ) -alkenyl- (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkynyl- (C 1 -C 6 ) -alkyl, hydroxy, (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) - Alkoxy- (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkoxy- (C 1
- a 1 , A 2 , A 3 and A 4 are the same or different and are independently N
- R 11 and R 12 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, (d-Ce) -alkyl, optionally substituted phenyl, heteroaryl, heterocyclyl, (C 3 -C 6 ) -cycloalkyl, (C 2 -C 6 ) - alkenyl, (C 2 -C 6) -alkynyl, (Ci-C6) alkoxy (Ci-C 6) alkyl, aryloxy (Ci-C 6) alkyl, (Ci-C 6) -haloalkyl, (Ci-C 6) haloalkoxy (Ci-C 6) alkyl, (Ci-C6) alkoxy (Ci-C 6) -haloalkyl, (Ci-C 6) haloalkoxy (Ci-C 6 ) -haloalkyl, (dC 6 ) -alkylthio (C 1 -C 6
- R 14 , R 17 and R 18 independently of one another represent hydrogen, (C 1 -C 6) -alkyl, fluorine, chlorine, bromine, iodine, (C 3 -C 6) -cycloalkyl, optionally substituted phenyl, heteroaryl, heterocyclyl, (C 2 -C 6) Alkenyl, aryl (C 1 -C 6) alkyl,
- a 6 , A 7 are the same or different and independently of one another are O (oxygen), S (sulfur), NH, N-OCH 3, N-CH 3 or the group CR 15 R 16 , although in each case two N-, O or S atoms are adjacent, and wherein R 15 and R 16 in the group CR 15 R 16 are identical or different
- R 15 and R 16 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, (d-Ce) -alkyl, optionally substituted phenyl, heteroaryl, heterocyclyl, (Cs-Ce) -cycloalkyl, (C 2 -C 6 ) - Alkenyl, (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl,
- a 8 is O (oxygen), S (sulfur), NH, N-CH 3 , N-OCH 3 or the moiety CHR 21 , and wherein R 21 in the moiety CHR 21 has the meaning as defined below,
- R 21 represents hydrogen, fluorine, chlorine, bromine, iodine, (C 1 -C 6) -alkyl, if appropriate
- R 24 , R 25 , R 26 , R 28 , R 29 and R 30 are each independently hydrogen, (Ci-Ce) alkyl, fluorine, chlorine, bromine, iodine, (Ca-CeJ-cycloalkyl, aryl, heteroaryl, heterocyclyl .
- a 9 is O (oxygen), S (sulfur), NH, N-CH 3 , N -OCH 3 or the moiety CHR 27 and wherein R 27 in the moiety CHR 27 has the meaning as defined below and
- R 27 is hydrogen, fluorine, chlorine, bromine, iodine, (Ci-Ce) - alkyl, optionally
- R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 17 , R 8 , R 19 , R 20 , R 22 , R 23 , R 24 , R 25 , R 26 , R 28 , R 29 and R 30 and A 1 to A 9 each have the meaning according to the definitions below and wherein the arrow for a bond to the respective group CR 6 in the aforementioned formulas (la) to (lo) .
- R 5 is hydroxy, (C 1 -C 6) -alkoxy, aryloxy, (C 3 -C 6 ) -cycloalkoxy, (C 2 -C 6 ) -alkenyloxy, (C 2 -C 6 ) -alkenyl- (C 1 -C 6 ) - alkyloxy, (C 1 -C 6 ) alkoxy- (C 1 -C 6 ) alkyloxy, (C 1 -C 6 ) -alkylcarbonyloxy, arylcarbonyloxy, heteroarylcarbonyloxy, (Ca-Ce) -cycloalkylcarbonyloxy, (C 1 -C 6 -alkoxycarbonyloxy, (C 2 -C 4 ) -alkoxy) -Ce) - alkenyloxycarbonyloxy, aryloxy- (C 1 -C 6 ) -alkyloxy, aryl- (C 1 -C 6
- heteroaryloxycarbonyl heteroaryl- (Ci-C6) -alkoxycarbonyl, heterocyclyKCrCe) -alkoxycarbonyl, heterocyclyloxycarbonyl, (C 2 -C 6) -alkenyl- (C 1 -C 6) -alkoxycarbonyl, (C 2 -C 6) -alkynyl- (C 1 -C 6) -alkoxycarbonyl, aryl - (C 2 -C 6) - alkynyloxycarbonyl, aryl- (C 2 -C 6) -alkenyloxycarbonyl, aminocarbonyl, (C 1 -C 6) -alkylaminocarbonyl, bis [(C 1 -C 6) -alkyl] aminocarbonyl, (C 1 -C 6) -alkyl [( C 1 -C 6) -alkyl] aminocarbonyl, (C 1 -C 6) -al
- R 7 , R 8 , R 9 and R 10 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, nitro, amino, cyano, (C 1 -C 8) -alkyl, optionally substituted phenyl, heteroaryl, (C 3 -C 6 ) -Cycloalkyl, (C 4 -C 6 ) -cycloalkenyl, (C 2 -C 5 ) -alkenyl, (C 2 -C 5 ) - Alkynyl, (C 2 -C 5 ) -alkenyl- (C 1 -C 5 ) -alkyl, (C 2 -C 5 ) -alkynyl- (C 1 -C 5 ) -alkyl, hydroxy, (C 1 -C 5 ) -alkoxy, ( Ci-C 5 ) -alkoxy- (Ci-C 5 ) -alkoxy, (Ci-C 5
- a 2 , A 3 and A 4 are the same or different and are each independently N (nitrogen) or the groupings CH, C-CH 3, CF, C-Cl, C-Br, Cl, C-OCF 3, C-OCH 3, C -CF 3, C-CO2H, C-CO2CH3 are, but in no case more than two N atoms are adjacent, and R 12 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, (C1-C5) - alkyl , optionally substituted phenyl, heteroaryl, heterocyclyl, (Cs-Ce) - cycloalkyl, (C 2 -C 5) alkenyl, (C 2 -C 5) alkynyl, (-C 5) haloalkyl, (C1-C5) - Haloalkoxy (Ci-C 5) alkyl, (Ci-C5) alkylthio (Ci-C5) alkyl, hydroxycarbonyl,
- a 5 represents S (sulfur), O (oxygen) or the groupings NH, N-CH 3 , N-CH 2 CH 3 , N-CH (CH 3 ) 2 , N-CO 2 t-Bu, N-aryl, N-heteroaryl, N-heterocyclyl is
- R 13 , R 14 , R 17 and R 18 are each independently hydrogen, (CrCr,) - alkyl, fluorine, chlorine, bromine, iodine, (C 3 -C 6) -cycloalkyl, optionally substituted phenyl, heteroaryl, heterocyclyl, (C 2 -C 5 ) -alkenyl, aryl- (Ci-C 5 ) -alkyl, (Ci-C 5 ) -alkoxy, (Ci-C 5 ) -Alkoxy- (Ci-C 5 ) -alkoxy, (Ci-C 5 ) Alkoxy- (C 1 -C 5 ) -alkyl, hydroxy, (C 1 -C 5 ) -haloalkyl, (C 1 -C-5) -haloalkylthio or
- R 13 and R 17 with the atoms to which they are attached form a completely saturated or partially saturated, optionally further substituted 5 to 7-membered ring,
- a 6 , A 7 are identical or different and independently of one another are O (oxygen), S (sulfur), NH, N-OCH 3, N-CH 3 or the group CR 15 R 16 , but in no case are two N , O or S atoms are adjacent, and wherein R 15 and R 16 in the group CR 15 R 16 are each the same or different
- R 15 and R 16 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, (C 1 -C 5 ) -alkyl, optionally substituted phenyl, heteroaryl, heterocyclyl, (C 3 -C 6) -cycloalkyl, (C 2 -C 5 ) - alkenyl, (Ci-C 5) alkoxy, (Ci-C 5) alkoxy (Ci-C 5) alkyl, (CrC 5) haloalkoxy, (Ci-C5) haloalkyl, (Ci-C 5 ) alkylthio, (Ci-C 5) haloalkylthio, (Ci-C5) alkylthio (Ci-C5) alkyl, hydroxycarbonyl, (Ci-C5) alkoxycarbonyl, (C3-Cr>) -cycloalkoxycarbonyl, aryl (C 1 -C 5) -alk
- R 19, R 20, R 22 and R 23 are independently hydrogen, (Ci-Cr>) alkyl, fluoro, chloro, bromo, iodo, (C3-C6) -cycloalkyl, optionally substituted phenyl, heteroaryl, heterocyclyl, ( C 2 -C 5) alkenyl, aryl (Ci-Cr.) - alkyl, (Ci-C 5) alkoxy, (Ci-C 5) -haloalkyl stand,
- a 8 is O (oxygen), S (sulfur), NH, N-CH 3 , N-OCH 3 or the moiety CHR 21 , and wherein R 21 in the moiety CHR 21 has the meaning as defined below,
- R 21 is hydrogen, fluorine, chlorine, bromine, iodine, (C 1 -C 6) -alkyl, if appropriate
- R 24 , R 25 , R 26 , R 28 , R 29 and R 30 independently of one another represent hydrogen, (C 1 -C 5 ) -alkyl, fluorine, chlorine, bromine, iodine, (C 1 -C 6 -cycloalkyl, aryl, heteroaryl, heterocyclyl, (C 2 -C 5) alkenyl, (Ci-C 5) alkoxy, (Ci-C5) haloalkyl, (Ci-C 5) alkylthio, (C1-C5) - haloalkylthio stand,
- a 9 is O (oxygen), S (sulfur), NH, N-CH 3 , N -OCH 3 or the moiety CHR 27 and wherein R 27 in the moiety CHR 27 has the meaning as defined below and R 27 represents hydrogen, fluorine, chlorine, bromine, iodine, (C 1 -C 5) -alkyl, optionally substituted phenyl, heteroaryl, heterocyclyl, (C 1 -C 6 -cycloalkyl, (C 2 -C 6) -alkenyl, (C 1 -C 6) ) alkoxy, (Ci-C 5) alkoxy (Ci-C 5) alkyl, (Ci-C 5) -haloalkoxy, (CrC 5) haloalkyl, (CrC 5) alkylthio, (Ci-Cr.
- haloalkylthio hydroxycarbonyl, (C Cr>) alkoxycarbonyl, (Ca-Ce cycloalkoxycarbonyl, aryl (CrCr>) - alkoxycarbonyl, aminocarbonyl, (d-Cs ⁇ alkylaminocarbonyl, bis [(Ci-C5) - alkyl] aminocarbonyl , (C 1 -C 12 -cycloalkylaminocarbonyl, aryl- (C 1 -C 6) -alkylaminocarbonyl, amino, (C 1 -C 6 -alkylamino, (C 3 -C 6) -cycloalkylamino, bis [(C 1 -C 5 ) -alkyl] -amino.
- R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 17 , R 18 , R 19 , R 20 , R 22 , R 23 , R 24 , R 25 , R 26 , R 28 , R 29 and R 30 and A 1 to A 9 each have the meaning according to the have the following definitions and wherein the arrow for a bond to the respective group CR 6 is in the abovementioned formulas (Ia) to (Ic),
- R 5 is hydroxy, methoxy, ethoxy, n-propyloxy, methylcarbonyloxy,
- Ethoxycarbonyloxy trimethylsilyloxy, triethylsilyloxy, triisopropylsilyloxy, thylphenylsilyloxy, tert-butyldimethylsilyloxy,
- R 6 represents fluorine, chlorine, bromine, iodine, cyano, cyanomethyl, trifluoromethyl
- Pentafluoroethyl difluoromethyl, nitro, amino, hydroxy, hydroxymethyl,
- Methoxyethoxycarbonyl ethoxyethoxycarbonyl, ethoxymethoxycarbonyl, methoxy-n-propyloxycarbonyl, ethoxy-n-propoxycarbonyl,
- Ethoxyethylaminocarbonyi (C2-C6) -alkinylaminocarbonyl, methylsulfonylamino, ethylsulfonylamino, iso-propylsulfonylamino, Cyclopropylsulfonylamino, Phenyisuifonylamino, p-chlorophenylsulfonylamino, o-chlorophenylsulfonylamino, m-chlorophenylsulfonylamino, p-fluorophenylsulfonylamino, o- fluorophenylsulfonylamino, m-fluorophenylsulfonylamino, p-lodphenylsulfonylamino, o-iodophenylsulfonylamino, m-iodophenylsulfon
- Ethylaminosulfonyl n-propylaminosulfonyl, iso-propylaminosulfonyl, n-butylaminosulfonyl, tert-butylaminosulfonyl, iso-butylaminosulfonyl,
- Aminoiminomethyl (Ci-C5) alkoxyiminomethyl, (Ci-C5) -Alkylaminoiminomethyl, bis [(Ci-C5) alkyl] aminoiminomethyl (C3-Cr>) -Cycloalkoxyiminomethyl, (CS-CG) - cycloalkyl- (Ci-C5 ) -alkoximinomethyl, aryloximinomethyl, aryl- (C 1 -C 5 ) -alkoxyiminomethyl, aryl- (C 1 -C 5 ) -alkylaminoiminomethyl, (C 2 -C 5 ) -alkenyloxyiminomethyl, aryiaminoiminomethyl, arylsulfonylaminoiminomethyl, heteroaryl- (C 1 -C 5 ) -acyl, heterocyclyl ( Ci-C 5 ) -alkyi,
- R 7 , R 8 , R 9 and R 10 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, nitro, amino, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, phenyl, cyclopropyl, cyclobutyl, hydroxy, methoxy, ethoxy,
- a ⁇ A 2 , A 3 and A 4 are the same or different and are independently N
- R 11 and R 12 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, phenyl, cyclopropyl, cyclobutyl, trifluoromethyl , Di-propyloxycarbonyl, n-propyloxycarbonyl
- R 13 , R 14 , R 17 and R 18 are independently hydrogen, methyl, ethyl, n-propyl, iso-propyl, n-butyl, fluorine, chlorine, bromine, iodine, trifluoromethyl or
- R 13 and R 17 with the atoms to which they are attached form a completely saturated or partially saturated, optionally further substituted 5 to 7-membered ring,
- a 6 , A 7 are identical or different and independently of one another are O (oxygen), S (sulfur), NH, N-OCH 3, N-CH 3 or the group CR 15 R 16 , but in no case are two N , O or S atoms are adjacent, and wherein R 15 and R 16 in the group CR 15 R 16 are each the same or different
- R 15 and R 16 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, phenyl, methoxy, ethoxy, trifluoromethyl,
- R 19 , R 20 , R 22 and R 23 are each independently hydrogen, methyl, ethyl, n-propyl, iso-propyl, fluorine, chlorine, bromine, iodine, phenyl, trifluoromethyl,
- a 8 is O (oxygen), S (sulfur), NH, N-CH 3 , N-OCH 3 or the moiety CHR 21 , and wherein R 21 in the moiety CHR 21 is as defined below, R 21 is Hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, methoxy, ethoxy,
- R 24 , R 25 , R 26 , R 28 , R 29 and R 30 independently of one another represent hydrogen, methyl, ethyl, n-propyl, isopropyl, fluorine, chlorine, bromine, iodine, phenyl, trifluoromethyl, methylthio,
- a 9 is O (oxygen), S (sulfur), NH, N-CH 3, N -OCH 3 or the moiety CHR 27 and wherein R 27 in the moiety CHR 27 has the meaning as defined below and
- R 27 represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, methoxy, ethoxy,
- Residue definitions apply both to the end products of the general formula (I) and correspondingly to the starting material or preparation required in each case for the preparation Intermediates. These remainder definitions can be combined with one another as desired, ie also between the specified preferred ranges.
- R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 17 , R 18 , R 19 , R 20 , R 22 , R 23 , R 24 , R 25 , R 26 , R 28 , R 29 and R 30 and A 1 to A 9 each have the meaning according to the following definitions and wherein the arrow for a bond to the respective group CR 6 in the general formula (I), for (Ci -C 7 ) -alkyl, (C 3 -C 7 ) -cycloalkyl, (C 4 -C 7 ) -cycloalkenyl, (C 2 -C 7 ) -alkenyl, (C 2 -C 7 ) -alkynyl, (C 2 -C 7) alkenyl (Ci-C7) alkyl, (C 2 -C 7) alkynyl (Ci-C7) alkyl, (
- R 3 and R 4 independently of one another represent hydrogen, halogen, (C 1 -C 7 ) -alkyl,
- R 7, R 8, R 9 and R 10 are independently hydrogen, halogen, nitro, amino, cyano, (Ci-C7) alkyl, aryl, heteroaryl, (C 3 -C 7) cycloalkyl, (C 4 -C 7 ) -cycloalkenyl, (C 2 -C 7 ) -alkenyl, (C 2 -C 7 ) -alkynyl, (C 2 -C 7 ) -alkenyl- (C 1 -C 7 ) -alkyl, (C 2 -) C 7 ) alkynyl (C 1 -C 7 ) -alkyl, hydroxy, (C 1 -C 7 ) -alkoxy, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkoxy, (C 1 -C 7 ) -alkoxy (C 1 -C 7 ) -alkyl, hydroxy- (C 1
- a 1 , A 2 , A 3 and A 4 are the same or different and are independently N
- R 11 and R 12 independently of one another represent hydrogen, halogen, (C 1 -C 7 ) -alkyl, aryl, heteroaryl, heterocyclyl, (C 3 -C 7 ) -cycloalkyl , (C 2 -C 7 ) -alkenyl, (C 2 -C 7) alkynyl, (-C 7) alkoxy, (Ci-C7) alkoxy (Ci-C7) alkyl, aryloxy (Ci-C7) alkyl, (C1-C7) - Haloalkoxy, (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -haloalkoxy- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) Haloalkoxy- (C 1 -C 7 )
- R 13 , R 14 , R 17 and R 18 are each independently hydrogen, (Ci-C-7) -alkyl, halogen, (C 3 -C 7 ) -cycloalkyl, aryl, heteroaryl, heterocyclyl, (C 2 -C 7 ) -Alkenyl, (C 2 -C 7 ) -alkenyl- (C 1 -C 7 ) -alkyl, aryl- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkoxy, (C 1 -C 7 ) -alkoxy (C 1 -C 7 ) -alkoxy, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, hydroxy, (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -haloalkylthio or
- R 13 and R 17 with the atoms to which they are attached form a completely saturated or partially saturated, optionally further substituted 5 to 7-membered ring,
- a 6 , A 7 are the same or different and independently of one another are O (oxygen), S (sulfur), NH, N-OCH 3, N-CH 3 or the group CR 15 R 16 , although in each case two N-, O or S atoms are adjacent, and wherein R 15 and R 16 in the group CR 15 R 16 are identical or different
- R 15 and R 16 independently of one another represent hydrogen, halogen, (C 1 -C 7 ) -alkyl, aryl, heteroaryl, heterocyclyl, (C 3 -C 7 ) -cycloalkyl, (C 2 -C 7 ) -alkenyl, (Ci-C 7 ) -alkoxy, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, aryloxy- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -haloalkoxy, (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -haloalkoxy (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -haloalkoxy
- R 19 , R 20 , R 22 and R 23 independently of one another represent hydrogen, (C 1 -C 4 ) -alkyl, halogen, (C 3 -C 7 ) -cycloalkyl, aryl, heteroaryl, heterocyclyl, (C 2 -C 7 ) alkenyl, aryl (Ci-C7) - alkyl, (Ci-C7) alkoxy, (Ci-C7) alkoxy (Ci-C7) alkoxy, (Ci-C7) alkoxy (Ci-C7) - alkyl, (dC 7) -haloalkyl stand,
- a 8 is O (oxygen), S (sulfur), NH, N-CH 3 , N-OCH 3 or the moiety CHR 21 , and wherein R 21 in the moiety CHR 21 has the meaning as defined below,
- R 21 is hydrogen, halogen, (Ci-C 7) alkyl, aryl, heteroaryl, heterocyclyl, (C3-C7) - cycloalkyl, (C 2 -C 7) alkenyl, (Ci-C7) alkoxy, ( Ci-C7) alkoxy (Ci-C7) alkyl, aryloxy (Ci-C7) alkyl, (Ci-C7) haloalkoxy, (dC 7) -haloalkyl, (dC 7) alkoxy (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -haloalkoxy- (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -alkylthio,
- (C 1 -C 7 ) -alkylaminocarbonyl bis [(C 1 -C 7 ) -alkyl] aminocarbonyl, (C 1 -C 7 ) -alkyl [(C 1 -C 7 ) -alkyl] aminocarbonyl, (C 1 -C 7 ) -alkyl [ (C 1 -C 7 ) -alkoxy] aminocarbonyl, (C 2 -C 7 ) -alkenylaminocarbonyl, (C 3 -C 7 ) -cycloalkylaminocarbonyl,
- R 24, R 25, R 26, R 28, R 29 and R 30 are independently hydrogen, (Ci-C7) alkyl, halogen, (C 3 -C 7) cycloalkyl, aryl, heteroaryl, heterocyclyl, ( C 2 -C 7 -alkenyl, (C 1 -C 7 ) -alkoxy, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkoxy, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) alkyl, (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -alkylthio, (C 1 -C 7 ) -haloalkylthio,
- a 9 is O (oxygen), S (sulfur), NH, N-CH 3 , N -OCH 3 or the moiety CHR 27 and wherein R 27 in the moiety CHR 27 has the meaning as defined below and R 27 represents hydrogen, halogen, (C 1 -C 7 ) -alkyl, aryl, heteroaryl, heterocyclyl, (C 3 -C 7 ) -cycloalkyl, (C 2 -C 7 ) -alkenyl, (C 1 -C 7 ) -alkoxy, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, aryloxy- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -haloalkoxy, (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) Alkylthio, (d-C7) -haloalkylthio,
- R 1 is (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, (C 4 -C 6 ) -cycloalkenyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl , (C 2 -C 6) alkenyl (Ci-C 6) alkyl, (C2-C6) alkynyl (Ci-C 6) alkyl, (Ci-C 6) alkoxy (Ci- C 6) alkyl, hydroxy (Ci-C 6) alkyl, (Ci-C 6) -haloalkyl, (C 2 -C 6) - haloalkenyl, (C 2 -C 6) haloalkynyl group,
- R 2, R 3 and R 4 independently of one another represent hydrogen, fluorine, (Ci-COE) alkyl, (C3-Ce) - cycloalkyl, (C 4 -C c) cycloalkenyl, (C 2 -C 6) alkenyl , (C 2 -C 6) -alkynyl, (C 2 -C 6) - alkenyl, (CrC 6) alkyl, (C 2 -C 6) alkynyl (Ci-C 6) alkyl, (Ci- C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, hydroxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkyl,
- R 5 is hydroxy, (Ci-Ce) alkoxy, aryloxy, (C3-C6) cycloalkyloxy, (C 2 -C 6) alkenyloxy, (C 2 -C 6) alkenyl (Ci-C 6) alkyloxy , (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyloxy, (C 1 -C 6 ) -alkylcarbonyloxy, arylcarbonyloxy, heteroarylcarbonyloxy, (Ca-Ce) -cycloalkylcarbonyloxy, (d-CeJ-alkoxycarbonyloxy, (C 2 -Ce) - alkenyloxycarbonyloxy, aryloxy- (Ci-C6) -alkyloxy, aryl- (Ci-C6) -alkyloxy, (Ci-Cr > ) - alkoxy- (Ci-C6) -al
- R 6 is (d-Ce) -alkylsulfonylaminocarbonyl, (C3-Ce) -
- C3-C6) cycloalkyl (Ci-C6) alkoxycarbonyl (Ci-C 6) alkyl, (C 2 -C 6) - alkenyloxycarbonyl (Ci-COE) alkyl, aryl (Ci-C6) alkoxycarbonyl- (C 1 -C 6) -alkyl, (C 1 -C 6) -alkylaminocarbonyl- (C 1 -C 6) -alkyl, aminocarbonyl- (C 1 -C 6) -alkyl,
- Aminoiminomethyl (CrCeJ-alkoxyiminomethyl, (C 1 -C 6) -alkyiaminoiminomethyl, bis [(C 1 -C 6) -alkyl] aminoiminomethyl, (Ca-CeJ-cycloalkoxyiminomethyl, (Ca-Ce) -cycloalkyl- (C 1 -C 6) -alkoximinomethyl, Aryloximinomethyl, aryl- (C 1 -C 6) -alkoxyiminomethyl, aryl- (C 1 -C 6) -alkylaminoiminomethyl, (C 2 -C 6) -alkenyloxyiminomethyl, aryiaminoiminomethyl, arylsulfonylaminoiminomethyl, hydroxyaminocarbonyl, (C 1 -Cf,) -alkoxyaminocarbonyl, aryl- Ce) - alkoxyaminocarbony
- R 7 , R 8 , R 9 and R 10 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, nitro, amino, cyano, (d-CeJ-alkyl, optionally substituted phenyl, heteroaryl, (C 3 -C 6 ) .
- cycloalkyl (C 4 -C 6) -cycloalkenyl, (C 2 -C 6) alkenyl, (C 2 -C 6) - alkynyl, (C2-C6) alkenyl (Ci-C 6) alkyl , (C 2 -C 6) alkynyl (Ci-C 6) alkyl, hydroxy, (Ci-C 6) alkoxy, (Ci-C6) alkoxy (Ci-C 6) alkoxy, ( Ci-C 6) alkoxy (Ci-C 6) alkyl, hydroxy (Ci-C 6) alkyl, (Ci-Ce) haloalkoxy, (Ci-C 6) -haloalkyl, (C 2 -C 6) - haloalkenyl, (C 2 -C 6) haloalkynyl, (Ci-C 6) haloalkoxy (Ci-C6) alkyl, (Ci
- a 1 , A 2 , A 3 and A 4 are the same or different and are independently N
- R 11 and R 12 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, (d-Ce) -alkyl, optionally substituted phenyl, heteroaryl, heterocyclyl, (Cs-Ce) -cycloalkyl, (C 2 -C 6 ) - alkenyl, (C 2 -C 6) -alkynyl, (Ci-C6) alkoxy (Ci-C 6) alkyl, aryloxy (CrC 6) alkyl, (CrC 6) -haloalkyl, (Ci-C6 Haloalkoxy- (C 1 -C 6 ) -alkyl,
- Aryloxycarbonyl aryl- (C 1 -C 6) -alkoxycarbonyl, (C 2 -C 6) -alkenyloxycarbonyl,
- R 13 , R 14 , R 17 and R 18 independently of one another represent hydrogen, (C 1 -C 6) -alkyl, fluorine, chlorine, bromine, iodine, (C 5 -C 12 -cycloalkyl, optionally substituted phenyl, heteroaryl, heterocyclyl, (C 2 -C 10) Cc,) - alkenyl, aryl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkoxy - (Ci-C 6 ) -alkyl, hydroxy, (d-Cr,) - haloalkyl, (Ci-CeJ-haloalkylthio or R 13 and R 17 with the atoms to which they are attached form a completely saturated or partially saturated,
- a 6 , A 7 are the same or different and are each independently O (oxygen), S (sulfur), NH, N-OCH 3 , N-CH 3 or the group CR 15 R 16 , but in no case two N -, O or S atoms are adjacent, and wherein R 15 and R 16 in the group CR 15 R 16 are identical or different
- R 5 and R 16 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, (d-Ce) -alkyl, optionally substituted phenyl, heteroaryl, heterocyclyl, (Ca-Ce) -cycloalkyl, (C 2 -C 6 ) - Alkenyl, (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl,
- R 19 , R 20 , R 22 and R 23 independently of one another represent hydrogen, (C 1 -C 6) -alkyl, fluorine, chlorine, bromine, iodine, (C 3 -C 6) -cycloalkyl, aryl, heteroaryl, heterocyclyl, (C 2 -C 6) ) Alkenyl, aryl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -haloalkyl,
- a 8 is O (oxygen), S (sulfur), NH, N-CH 3, N -OCH 3 or the moiety CHR 21 , and wherein R 21 in the moiety CHR 21 has the meaning as defined below,
- R 21 is hydrogen, fluorine, chlorine, bromine, iodine, (C 1 -C 6) -alkyl, if appropriate
- R 24 , R 25 , R 26 , R 28 , R 29 and R 30 independently of one another are hydrogen, (C 1 -C 6 ) -alkyl, fluorine, chlorine, bromine, iodine, (C 1 -C 4 -cycloalkyl, aryl, heteroaryl , Heterocyclyl, (C 2 -C 6 ) -alkenyl, (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -haloalkyl, (C 1 -C 6 ) -alkylthio, (C 1 -C 6 ) -haloalkylthio,
- a 9 is O (oxygen), S (sulfur), NH, N-CH 3 , N-OCH 3 or the moiety CHR 27 and wherein R 27 in the moiety CHR 27 has the meaning as defined below and
- R 27 is hydrogen, fluorine, chlorine, bromine, iodine, (C 1 -C 6) -alkyl, if appropriate
- R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 4 , R 17 , R 18 , R 19 , R 20 , R 22 , R 23 , R 24 , R 25 , R 26 , R 28 , R 29 and R 30 and A 1 to A 9 each have the meaning according to the definitions below and wherein the arrow for a bond to the respective group CR 6 in the aforementioned formulas (la) to (lo) .
- R 5 is hydroxy, (C 1 -C 5) -alkoxy, aryloxy, (C 3 -C 6 ) -cycloalkyloxy, (C 2 -C 6 ) -alkenyloxy, (C 2 -C 6 ) -alkenyl- (C 1 -C 6 ) -alkyloxy, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyloxy, (C 1 -C 6 ) -alkylcarbonyloxy, arylcarbonyloxy, heteroarylcarbonyloxy, (C 3 -C 6 ) -cycloalkylcarbonyloxy, (C 1 -C 6 -alkoxycarbonyloxy, (C 2 -C 4 ) -cyclocarbonyloxy Alkenyloxycarbonyloxy, aryloxy- (Ci-Cr,) -alkyloxy, aryl- (C 1 -C
- R 6 is (C 1 -C 5 ) -alkylsulfonylaminocarbonyl, (C 3 -G 5) -
- Aminoiminomethyl (CrCr-alkoxyiminomethyl, (C 1 -C 6) -alkylaminoiminomethyl, bis [(C 1 -C 6) -alkyl] aminoiminomethyl, (C 3 -C 6) -cycloalkoxyiminomethyl, (C 3 -C 6) -cycloalkyl- (C 1 -C 6) -alkoximinomethyl , Aryloximinomethyl, aryl- (Ci-Ce) -alkoxyiminomethyl, aryl- (Ci-C6) -alkylaminoiminomethyl, (C2-Ce) -alkenyloxyiminomethyl, arylaminoiminomethyl, arylsulfonylaminoiminomethyl, hydroxyaminocarbonyl, (Ci-CeJ-alkoxyaminocarbonyl, aryl- (Ci-Ce ) - alkoxyaminocarbon
- R 7 , R 8 , R 9 and R 10 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, nitro, amino, cyano, (C 1 -C 5) -alkyl, optionally substituted phenyl, heteroaryl, (C 3 - C 6) cycloalkyl, (C 4 -C 6) -cycloalkenyl, (C 2 -C 5) alkenyl, (C2-C5) - alkynyl, (C2-C5) alkenyl (Ci-C 5) - alkyl, (C 2 -C 5 ) -alkynyl- (C 1 -C 6 -alkyl), hydroxy, (C 1 -C 5 ) -alkoxy, (C 1 -C 5 ) -alkoxy- (C 1 -C 5 ) -alkoxy, ( Ci-C 5) alkoxy (Ci-C 5) alkyl, hydroxy (Ci
- a 1 , A 2 , A 3 and A 4 are the same or different and are independently N
- R 11 and R 12 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, (C 1 -C 5) -alkyl, optionally substituted phenyl, heteroaryl, heterocyclyl, (Cs-Ce) -cycloalkyl.
- a 5 represents S (sulfur), O (oxygen) or the groupings NH, N-CH 3 , N-CH 2 CH 3 , N-CH (CH 3 ) 2 , N-CO 2 t-Bu, N-aryl, N-heteroaryl, N-heterocyclyl is
- R 13 , R 14 , R 17 and R 18 independently of one another represent hydrogen, (C 1 -C 6 -alkyl, fluorine, chlorine, bromine, iodine, (C 3 -C 6) -cycloalkyl, optionally substituted phenyl, heteroaryl, heterocyclyl, (C 2 -C 5) alkenyl, aryl (-C 5) alkyl, (Ci-C 5) alkoxy, (C 1 -C 5 ) -alkoxy- (C 1 -C 5 ) -alkoxy, (C 1 -C 5 ) -alkoxy- (C 1 -C 5 ) -alkyl, hydroxy, (C 1 -C 5 ) -haloalkyl, (C 1 -C 6 -haloalkylthio) or
- R 13 and R 17 with the atoms to which they are attached form a completely saturated or partially saturated, optionally further substituted 5 to 7-membered ring,
- a 6 , A 7 are identical or different and independently of one another are O (oxygen), S (sulfur), NH, N-OCH 3, N-CH 3 or the group CR 15 R 16 , but in no case are two N , O or S atoms are adjacent, and wherein R 15 and R 16 in the group CR 15 R 16 are each the same or different
- R 15 and R 16 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, (C 1 -C 5 ) -alkyl, optionally substituted phenyl, heteroaryl, heterocyclyl, (C 1 -C 6) -cycloalkyl, (C 2 -C 5 ) -alkenyl , (C 1 -C 5 ) -alkoxy, (C 1 -C 5 ) -alkoxy- (C 1 -C 5 ) -alkyl,
- R 19 , R 20 , R 22 and R 23 are each independently hydrogen, (Ci-Cr,) - alkyl, fluorine, chlorine, bromine, iodine, (Ca-CeJ-cycloalkyl, optionally substituted phenyl, heteroaryl, heterocyclyl, (C 2 -C 5) alkenyl, aryl (Ci-C 5) alkyl, (Ci-C 5) alkoxy, (Ci-Cs) -haloalkyl stand,
- a 8 is O (oxygen), S (sulfur), NH, N-CH 3 , N-OCH 3 or the moiety CHR 2 and wherein R 21 in the moiety CHR 21 has the meaning as defined below, R 21 is hydrogen, fluorine, chlorine, bromine, iodine, (C 1 -C 6) -alkyl, if appropriate
- R 24 , R 25 , R 26 , R 28 , R 29 and R 30 independently of one another represent hydrogen, (C 1 -C 5 ) -alkyl, fluorine, chlorine, bromine, iodine, (C 1 -C 6 -cycloalkyl, aryl, heteroaryl, heterocyclyl, (C 2 -C 5) alkenyl, (Ci-C 5) alkoxy, (Ci-C5) haloalkyl, (CrC 5) alkylthio, (C1-C5) - haloalkylthio stand,
- a 9 is O (oxygen), S (sulfur), NH, N-CH 3 , N-OCH 3 or the moiety CHR 27 and wherein R 27 in the moiety CHR 27 has the meaning defined below and R 27 is hydrogen , Fluorine, chlorine, bromine, iodine, (C 1 -C 8) -alkyl, if appropriate
- R 17 , R 18 , R 19 , R 20 , R 22 , R 23 , R 24 , R 25 , R 26 , R 28 , R 29 and R 30 and A 1 to A 9 each have the meaning as defined below, and where the arrow for a bond to the respective grouping CR 6 in the abovementioned formulas (Ia) to (Ic) is hydroxyl, methoxy, ethoxy, n-propyloxy, methylcarbonyloxy,
- Cyclopentylaminocarbonyl cyclohexylaminocarbonyl, piperidinyl-N-carbonyl, pyrrolidinyl-N-carbonyl, cyanomethylaminocarbonyl, cyanoethylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, diisopropylaminocarbonyl, methoxyethylaminocarbonyl, ethoxyethylaminocarbonyl, formyl,
- Cyclopropylmethoxyiminomethyl (C 1 -C 5) -alkylsulfonylaminocarbonyl, (C 3 -C 5) -cycloalkylsulfonylaminocarbonyl, (C 3 -C 6) -cycloalkyl- (C 1 -C 5) -alkoxycarbonyl, aryloxycarbonyl, (C 2 -C 5) -alkenyloxycarbonyl, (C 2 -C 5) -alkynyloxycarbonyl, (C2-C5) alkenyloxy (CRC5) -alkoxycarbonyl
- Aminocarbonyl- (C 1 -C 5) -alkyl bis [(C 1 -C 5) -alkyl] aminocarbonyl- (C 1 -C 5) -alkyl, (C 3 -C 5) -cycloalkylaminocarbonyl- (C 1 -C 5) -alkyl, aryl- (C 1 -C 5) -alkyl alkylaminocarbonyl (d-Cr>) alkyl, heteroaryl (Ci-Cr>) alkylaminocarbonyl (Ci-C5) alkyl, cyano- (Ci-C5) alkylaminocarbonyl (CRC5) alkyl, (Ci-C5 ) -Haloalkylaminocarbonyl- (Ci-C 5) alkyl, (C2-C5) alkynyl (Ci-C5) alkylaminocarbonyl (Ci-C 5) alkyl, (C 3 -
- R 7 , R 8 , R 9 and R 10 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine,
- a 1 , A 2 , A 3 and A 4 are the same or different and are independently N
- R 11 and R 12 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, phenyl, cyclopropyl, cyclobutyl, trifluoromethyl , Di-propyloxycarbonyl, n-propyloxycarbonyl
- R 13 , R 14 , R 17 and R 18 are independently hydrogen, methyl, ethyl, n-propyl, iso-propyl, n-butyl, fluorine, chlorine, bromine, iodine, trifluoromethyl or
- R 13 and R 17 with the atoms to which they are attached form a completely saturated or partially saturated, optionally further substituted 5 to 7-membered ring,
- a 6 , A 7 are identical or different and independently of one another are O (oxygen), S (sulfur), NH, N-OCH 3, N-CH 3 or the group CR 15 R 16 , but in no case are two N , O or S atoms are adjacent, and wherein R 15 and R 16 in the group CR 15 R 16 are each the same or different
- R 15 and R 16 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, phenyl, methoxy, ethoxy, trifluoromethyl,
- R 19 , R 20 , R 22 and R 23 are each independently hydrogen, methyl, ethyl, n-propyl, iso-propyl, fluorine, chlorine, bromine, iodine, phenyl, trifluoromethyl,
- a 8 is O (oxygen), S (sulfur), NH, N-CH 3 , N-OCH 3 or the moiety CHR 21 , and wherein R 21 in the moiety CHR 21 is as defined below, R 21 is Hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, methoxy, ethoxy,
- R 24 , R 25 , R 26 , R 28 , R 29 and R 30 independently represent hydrogen, methyl, ethyl, n-propyl, iso-propyl, fluorine, chlorine, bromine, iodine, phenyl, trifluoromethyl, methylthio.
- a 9 is O (oxygen), S (sulfur), NH, N-CH 3 , N -OCH 3 or the moiety CHR 27 and wherein R 27 in the moiety CHR 27 has the meaning as defined below and
- R 27 represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, methoxy, ethoxy,
- arylsulfonyl is optionally substituted phenylsulfonyl or optionally substituted polycyclic arylsulfonyl, here in particular optionally substituted naphthylsulfonyl, for example substituted by fluorine, chlorine, bromine, iodine, cyano, nitro, alkyl, haloalkyl, haloalkoxy, amino,
- Alkylamino, alkylcarbonylamino, dialkylamino or alkoxy groups
- cycloalkylsulfonyl alone or as part of a chemical group - is optionally substituted Cycloalkylsulfonyl, preferably having 3 to 6 carbon atoms such as cyclopropylsulfonyl, cyclobutylsulfonyl, cyclopentylsulfonyl or cyclohexylsulfonyl.
- alkylsulfonyl alone or as part of a chemical group - is straight-chain or branched alkylsulfonyl, preferably having 1 to 8, or having 1 to 6 carbon atoms such as methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl , sec-butylsulfonyl and tert-butylsulfonyl.
- heteroarylsulfonyl is optionally substituted
- substituted polycyclic heteroarylsulfonyl here in particular optionally substituted quinolinylsulfonyl, for example substituted by fluorine, chlorine, bromine, iodine, cyano, nitro, alkyl, haloalkyl, haloalkoxy, amino, alkylamino,
- alkylcarbonylamino, dialkylamino or alkoxy groups alkylcarbonylamino, dialkylamino or alkoxy groups.
- alkylthio alone or as part of a chemical group - represents straight-chain or branched S-alkyl, preferably having 1 to 8, or having 1 to 6 carbon atoms, such as, for example, methylthio, ethylthio, n-propylthio, isopropylthio, n- Butylthio, isobutylthio, sec-butylthio and tert-butylthio.
- Alkenylthio represents an alkenyl radical bonded via a sulfur atom
- alkynylthio represents an alkynyl radical bonded via a sulfur atom
- cycloalkylthio represents a cycloalkyl radical bonded via a sulfur atom
- cycloalkenylthio represents a cycloalkenyl radical bonded via a sulfur atom
- Alkoxy means an alkyl radical bonded through an oxygen atom
- alkenyloxy represents an alkynyl radical bonded via an oxygen atom
- alkynyloxy represents an alkynyl radical bonded via an oxygen atom
- cycloalkyloxy denotes a cycloalkyl radical bonded via an oxygen atom
- cycloalkenyloxy denotes a cycloalkenyl radical bonded via an oxygen atom
- aryl means an optionally substituted mono-, bi- or polycyclic aromatic system having preferably 6 to 14, in particular 6 to 10 ring C atoms, for example phenyl, naphthyl, anthryl, phenanthrenyl, and the like, preferably phenyl.
- optionally substituted aryl also includes polycyclic systems, such as tetrahydronaphthyl, indenyl, indanyl, fluorenyl, biphenylyl, the binding site being on the aromatic system.
- Aryl is also generally known from the term “optionally substituted phenyl ".
- Preferred aryl substituents here are, for example, hydrogen, halogen, alkyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, halocycloalkyl, alkenyl, alkynyl, aryl,
- heterocyclic ring preferably contains 3 to 9 ring atoms, especially 3 to 6
- Ring atoms, and one or more, preferably 1 to 4, in particular 1, 2 or 3 heteroatoms in the heterocyclic ring, preferably from the group N, O, and S, but not two oxygen atoms should be directly adjacent, as
- heteroatom from the group N, O and S 1 - or 2- or 3-pyrrolidinyl, 3,4-dihydro-2H-pyrrole-2 or 3-yl, 2, 3-dihydro-1 H-pyrrole 1- or 2- or
- 2- or 3-tetrahydrothiophenyl 2,3-dihydrothiophene-2 or 3 or 4 or 5-yl; 2,5-dihydrothiophene-2 or 3-yl; Tetrahydro-2H-thiopyran-2- or 3- or 4-yl; 3,4-dihydro-2H-thiopyran-2 or 3 or 4 or 5 or 6-yl; 3,6-dihydro-2H-thiopyran-2 or 3 or 4 or 5 or 6-yl; 2H-thiopyran-2 or 3 or 4 or 5 or 6-yl; 4H-thiopyran-2- or 3- or 4-yl.
- Preferred 3-membered and 4-membered heterocycles are, for example, 1- or 2-aziridinyl, oxiranyl, thiiranyl, 1- or 2- or 3-azetidinyl, 2- or 3-oxetanyl, 2- or 3-thietanyl, 1,3 -Dioxetan-2-yl. Further examples of
- Heterocyclyl are a partially or fully hydrogenated heterocyclic radical having two heteroatoms from the group N, O and S, such as 1- or 2- or 3- or 4-pyrazolidinyl; 4,5-dihydro-3H-pyrazole-3- or 4- or 5-yl; 4,5-dihydro-1H-pyrazole-1 or 3 or 4 or 5-yl; 2,3-dihydro-1H-pyrazole-1 - or 2- or 3- or 4- or 5-yl; 1- or 2- or 3- or 4-imidazolidinyl; 2,3-dihydro-1H-imidazole-1 - or 2- or 3- or 4-yl; 2,5-dihydro-1H-imidazole-1 - or 2- or 4- or 5-yl; 4,5-dihydro-1H-imidazole-1 - or 2- or 4- or 5-yl; Hexahydropyridazine-1 or 2- or 3- or 4-yl; 1,2,3,4-tetrahydropyridazine-1 -
- 5- or 6-yl 5,6-dihydro-4H-1,2-oxazine-3- or 4- or 5- or 6-yl; 2H-1, 2-oxazine-2 or 3 or 4 or 5 or 6-yl; 6H-1, 2-oxazine-3 or 4 or 5 or 6-yl; 4H-1, 2-oxazine-3 or 4 or 5 or 6-yl; 1,3-oxazinan-2 or 3 or 4 or 5 or 6-yl;
- 6- or 7-yl 1,4-oxazepine-2- or 3- or 5- or 6- or 7-yl; isothiazolidine-2- or 3- or 4- or 5-yl; 2,3-dihydroisothiazole-2- or 3- or 4- or 5-yl; 2,5-dihydroisothiazole-2 or 3 or 4 or 5-yl; 4,5-dihydroisothiazole-3 or 4 or 5-yl; 1,3-thiazolidine-2- or 3- or 4- or 5-yl; 2,3-dihydro-1, 3-thiazole-2 or 3 or
- heterocyclyl are a partially or fully hydrogenated heterocyclic radical having 3 heteroatoms from the group N, O and S, such as, for example, 1, 4,2-dioxazolidin-2 or 3 or 5-yl; 1, 4,2-dioxazol-3 or 5-yl; 1,2,2-dioxazinane-2- or -3- or 5- or 6-yl; 5,6-dihydro-1,2,2,2-dioxazine-3- or 5- or 6-yl; 1, 4,2-dioxazine-3- or 5- or 6-yl; 1, 4 ?
- Structural examples of optionally further substituted heterocycles are also listed below:
- heterocycles listed above are preferably, for example, hydrogen, halogen, alkyl, haloalkyl, hydroxy, alkoxy, cycloalkoxy, aryloxy, alkoxyalkyl,
- Suitable substituents for a substituted heterocyclic radical are the substituents mentioned below, in addition to oxo and thioxo.
- Oxo group as a substituent on a ring C atom then means, for example, a carbonyl group in the heterocyclic ring.
- lactones and lactams are preferably also included.
- the oxo group may also be attached to the hetero ring atoms, which may exist in different oxidation states, e.g. in the case of N and S, for example, the divalent groups N (O), S (O) (also known as SO) and S (O) 2 (also abbreviated to SO 2) occur and form in the heterocyclic ring.
- N (O), S (O) (also known as SO) and S (O) 2 also abbreviated to SO 2
- heteroaryl is heteroaromatic
- Heteroaryls of the invention are, for example, 1H-pyrrol-1-yl; 1H-pyrrol-2-yl; 1H-pyrrol-3-yl; Furan-2-yl; Furan-3-yl; Thien-2-yl; Thien-3-yl, 1H-imidazole-1-yl; 1 H-imidazol-2-yl; 1 H -imidazol-4-yl; 1 H -imidazol-5-yl; 1H-pyrazole-1-yl; 1H-pyrazol-3-yl; 1H-pyrazol-4-yl; 1 H-pyrazol-5-yl, 1 H-1, 2,3-triazol-1-yl, 1 H-1, 2,3-triazol-4-yl, 1 H-1, 2, 3-triazole-5 yl, 2H-1, 2,3-triazol-2-yl, 2H-1, 2,3-triazol-4-yl, 1H-1, 2,4-triazol-1-yl
- heteroaryl groups according to the invention may furthermore be substituted by one or more identical or different radicals. If two adjacent carbon atoms are part of another aromatic ring, they are fused heteroaromatic systems, such as benzo-fused or multiply annelated heteroaromatics.
- quinolines for example quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl
- Isoquinolines e.g., isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl, isoquinolin-8-yl
- quinoxaline for example quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl
- quinoxaline e.g., isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-
- quinazoline cinnoline; 1,5-naphthyridine; 1,6-naphthyridine; 1,7-naphthyridine; 1,8-naphthyridine; 2,6-naphthyridine; 2,7-naphthyridine; phthalazine; Pyridopyrazine;
- heteroaryl are also 5- or 6-membered benzo-fused rings from the group 1H-indol-1-yl, 1H-indol-2-yl, 1H-indol-3-yl, 1H-indole-4 yl, 1H-indol-5-yl, 1H-indol-6-yl, 1H-indol-7-yl, 1-benzofuran-2-yl, 1-benzofuran-3-yl, 1-benzofuran-4 -yl, 1-benzofuran-5-yl, 1-benzofuran-6-yl, 1-benzofuran-7-yl, 1-benzothiophen-2-yl, 1-benzothiophen-3-yl, 1-benzothiophen-4-yl , 1-benzothiophene-5-yl, 1-benzothiophene
- halogen means, for example, fluorine, chlorine, bromine or iodine.
- halogen means, for example, a fluorine, chlorine, bromine or iodine atom.
- alky Denotes a straight-chain or branched, open-chain, saturated hydrocarbon radical which is optionally monosubstituted or polysubstituted
- Preferred substituents are halogen atoms, alkoxy, haloalkoxy, cyano, alkylthio, haloalkylthio, amino or nitro groups, more preferably are
- Haloalkyl Methoxy, methyl, fluoroalkyl, cyano, nitro, fluoro, chloro, bromo or iodo.
- Haloalkyl "- alkenyl” and “alkynyl” mean the same or different
- monohaloalkyl such.
- Perhaloalkyl such.
- B. CCI 3 . CCIF 2 , CFCI 2 , CF 2 CCIF 2 , CF2CCIFCF3;
- Polyhaloalkyl such as CH 2 CHFCI, CF 2 CCIFH, CF 2 CBrFH, CH 2 CF 3 ;
- perhaloalkyl also encompasses the term perfluoroalkyl.
- Partially fluorinated alkyl means a straight-chain or branched, saturated
- Hydrocarbon which is mono- or polysubstituted by fluorine, wherein the corresponding fluorine atoms as substituents on one or more
- Hydrocarbon chain can be located, such as. B. CHFCH3, CH 2 CH 2 F, CH 2 CH 2 CF 3, CHF 2, CH 2 F, CHFCF 2 CF 3 partially fluorinated haloalkyl is a straight or branched, saturated hydrocarbon which is substituted with at least one fluorine atom by re halogen atoms, all others possibly present
- Halogen atoms are selected from the group fluorine, chlorine or bromine, iodine.
- the corresponding halogen atoms may be present as substituents on one or more different carbon atoms of the straight-chain or branched hydrocarbon chain.
- Partially fluorinated haloalkyl also includes the
- Haloalkoxy is, for example, OCF 3 , OCHF 2 , OCH 2 F, OCF 2 CF 3 , OCH 2 CF 3 and OCH 2 CH 2 Cl;
- (C 1 -C 4) -alkyl exemplified herein means a
- Carbon atoms corresponding to the range for C atoms, ie, the radicals include methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl.
- General alkyl radicals having a larger specified range of carbon atoms eg. As "(Ci-Ce) - alkyl", accordingly also include straight-chain or branched alkyl radicals with a larger number of carbon atoms, ie according to the example also the alkyl radicals with 5 and 6 carbon atoms.
- Carbon skeletons e.g. with 1 to 6 C atoms or with unsaturated groups having 2 to 6 C atoms, preferred.
- Alkyl radicals also in the assembled radicals such as alkoxy, haloalkyl, etc., mean e.g.
- alkenyl in particular also includes straight-chain or branched open-chain hydrocarbon radicals having more than one double bond, such as 1,3-butadienyl and 1,4-pentadienyl, but also allenyl or cumulenyl radicals having one or more cumulated double bonds, such as For example, allenyl (1,2-propadienyl), 1,2-butadienyl and 1,2,3-pentatrienyl.
- Alkenyl is, for example, vinyl, which may optionally be substituted by further alkyl radicals, eg Pro p-1 -ene-1-yl , But-1 - en-1 -yl, allyl, 1-methyl-prop-2-en-1-yl, 2-methyl-prop-2-en-1-yl, but-2-en-1-yl , 1-methylbut-3-en-1-yl and 1-methylbut-2-en-1-yl, 2-methyl-prop-1 -ene-1-yl,
- alkynyl in particular also includes straight-chain or branched open-chain hydrocarbon radicals having more than one triple bond or else having one or more triple bonds and one or more double bonds, for example 1,3-butatrienyl or 3-penten-1-yn-1 -yl.
- C 2 -C 6) -alkynyl is, for example, ethynyl, propargyl, 1-methylprop-2-yn-1-yl, 2-butynyl,
- cycloalkyl means a carbocyclic saturated ring system preferably having 3-8 ring C atoms, eg, cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl In the case of optionally substituted cycloalkyl, cyclic systems having substituents are included, with substituents also having a
- an alkylidene group such as methylidene, are included.
- optionally substituted cycloalkyl also become
- polycyclic aliphatic systems such as, for example, bicyclo [1, 1] -butan-1-yl, bicyclo [1, 1] -butan-2-yl, bicyclo [2.1.0] pentan-1-yl, bicyclo [2.1 .0] pentan-2-yl, bicyclo [2.1.0] pentan-5-yl, bicyclo [2.2.1] hept-2-yl (norbornyl), bicyclo [2.2.2] octan-2-yl, adamantane 1 -yl and adamantan-2-yl.
- (C3-C7) cycloalkyl means a shorthand notation for cycloalkyl having from three to seven carbon atoms corresponding to the range of C atoms.
- spirocyclic aliphatic systems are also included, such as spiro [2.2] pent-1-yl, spiro [2.3] hex-1-yl,
- Cycloalkenyl means a carbocyclic, non-aromatic, partially unsaturated ring system preferably having 4-8 C atoms, for example 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, or 1-cyclohexenyl, 2-
- Alkylidene group such as methylidene
- Alkylidene group such as methylidene
- the explanations for substituted cycloalkyl apply correspondingly.
- Cycloalkylidene means a carbocyclic radical which is bonded via a double bond.
- stannyl stands for a further substituted radical containing a tin atom
- Germanyl is analogous to a further substituted radical which is a
- Zeroconyl represents a further substituted radical containing a zirconium atom.
- Hafnyl represents a further substituted radical containing a hafnium atom.
- Boryl represents a further substituted radical containing a hafnium atom.
- Boryl is further substituted and optionally cyclic groups, each containing a boron atom.
- Plumbanyl represents a further substituted radical containing a lead atom.
- Hydra rgyl stands for a further substituted radical containing a mercury atom.
- Al stands for a further substituted radical containing an aluminum atom.
- Magnnesyl represents a further substituted radical containing a magnesium atom.
- Zincyl represents a further substituted radical containing a zinc atom.
- the compounds of the general formula (I) can exist as stereoisomers.
- the possible stereoisomers defined by their specific spatial form, such as enantiomers, diastereomers, Z and E isomers, are all encompassed by the formula (I). If, for example, one or more alkenyl groups are present, diastereomers (Z and E isomers) can occur. For example, if one or more asymmetric carbon atoms are present, enantiomers and diastereomers may occur.
- Stereoisomers can be obtained from the resulting mixtures in the preparation by conventional separation methods. The chromatographic separation can be used both on an analytical scale for
- stereoisomers can be selectively prepared by using stereoselective reactions using optically active sources and / or adjuvants.
- the invention thus also relates to all stereoisomers which comprises the general formula (I) but are not specified with their specific stereoform, and mixtures thereof Synthesis:
- the 1 - (arylethynyl) -, 1- (heteroarylethynyl) -, 1- (heterocyclylethynyl) - and 1 - (cycloalkenylethynyl) cyclohexanols of the general formula (I) according to the invention can be prepared starting from known processes (compare Qing et al. J. Fluorine Chem. 2000, 101, 31; WO2009005794; Node et al., Bioorg. Med. Chem., 2007, 15, 2736; Schmidt et al., Can. J. Chem., 1973, 51, 3620; Zhu et al., Org Lett. 201 1, 13, 684).
- Alkynylcyclohexanol backbones were optimized and replaced by alternative
- Cyclohexanone either directly with a lithium acetylide-ethylenediamine complex in a suitable polar aprotic solvent (eg tetrahydrofuran) or in two steps by reaction with trimethylsilylacetylene and LDA
- a suitable carbonate base eg.
- Triphenylphosphine or bis (Cycloacta-1, 5-dienyl) lridiumchiorid in combination with a bidentate ligand for example, 2.2 '-bis (diphenylphosphino) -1, 1' - binaphthyl or 1 .4-bis (diphenylphosphino) butane) and a suitable copper (I) halide (eg copper (I) iodide) in a suitable solvent mixture of an amine and a polar aprotic solvent (eg diisopropylamine and toluene or triethylamine and tetrahydrofuran) (Scheme 1 ).
- R 1 , R 2 , R 3 , R 4 , R 6 and Q in the following Scheme 1 have the meanings defined above.
- the substituted 1 - (arylethynyl) -, 1- (heteroarylethynyl) -, 1- (heterocyclylethynyl) - and 1- (cycloalkenylethynyl) -cyclohexanols (1.1) can be added by indium salt-mediated addition (eg with indium (II trifluoromethanesulfonate, indium (III) bromide, indium (III) chloride, indium (II) iodide) of an appropriately substituted aryl, cycloalkenyl or heteroaryl alkyne to an appropriately substituted one
- indium salt-mediated addition eg with indium (II trifluoromethanesulfonate, indium (III) bromide, indium (III) chloride, indium (II) iodide
- Cyclohexanone using a suitable amine base eg diisopropylamine, triethylamine, diisopropylethylamine, biscyclohexyl (methyl) amine, N-methylpiperidine, 1,8-diazabicyclo [5.4.0] undec-7-ene
- a suitable amine base eg diisopropylamine, triethylamine, diisopropylethylamine, biscyclohexyl (methyl) amine, N-methylpiperidine, 1,8-diazabicyclo [5.4.0] undec-7-ene
- R 1 , R 2 , R 3 , R 4 , R 6 and Q in the following Scheme 2 have the meanings defined above.
- the further substituted aryl, cycloalkenyl or heteroarylalky used here can be prepared starting from the corresponding triflates by a palladium catalyst-mediated coupling with trimethylsilylacetylene (compare Org. Lett. 2005, 7, 1363).
- Alkynylcyclohexanols (1.1) can be prepared by reaction with a suitable
- a suitable base e.g., 2,6-lutidine
- a suitable polar aprotic solvent e.g., dichloromethane
- this reaction is described in Scheme 3 using triethylsilyl trifluoromethanesulfonate.
- a suitable gold catalyst for example gold (III) bromide, gold (III) chloride
- the substituted (E) -configured 1-arylvinyl-, 1-heteroarylvinyl-, 1-cycloalkenylvinylcyclohexanols (I.5) can be prepared by reduction of the Aicyruppe of the corresponding substituted 1- (arylethynyl) -, 1 - (heteroarylethynyl) -, 1 - (Heterocyclylethynyl) - and 1 - (cycloalkenylethynyl) cyclohexanols (1.1)
- suitable aluminum hydride reagents eg sodium bis (2-methoxyethoxy) aluminum hydride or lithium aluminum hydride
- a suitable polar aprotic solvent eg tetrahydrofuran
- Borohydride reagents eg sodium borohydride
- a suitable polar protic solvent eg methanol
- Butanol eg Helvetica Chimica Acta 1986, 69, 368
- a suitable transition metal catalyst eg tris (acetonitrile) ruthenium-l, 2,3,4,5-pentamethylcyclopentadienylhexafluorophosphate or tris (acetonitrile Ruthenium cyclopentadienyl hexafluorophosphate, see J. Am. Chem.
- Reaction conditions can be obtained in the hydrogenation of the triple bond as further reaction products and the corresponding inventive (Z) -configured analogs.
- R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and Q have the previously defined meanings in Scheme 4.
- Example numbers correspond to the numbers given in Tables 1 to XX below.
- Diastereomeric mixtures are given either the respectively significant signals of both diastereomers or the characteristic signal of the main diastereomer.
- 2,2,6-Trimethylcyclohexanone 200 mg, 1.43 mmol was dissolved in a round bottom flask under argon in abs. Tetrahydrofuran (3 ml) was dissolved and added dropwise to a solution of a lithium acetylide-ethylenediamine complex (171 mg, 1.85 mmol, 85% content) in abs. Tetrahydrofuran (2 ml). The reaction solution was stirred for 2 h after the addition at room temperature, then treated with water and concentrated under reduced pressure. The remaining residue was mixed with water and dichloromethane and the aqueous phase extracted several times with dichloromethane. The combined organic phases were over magnesium sulfate dried, filtered and concentrated under reduced pressure.
- reaction mixture was stirred for 4 h at room temperature and then treated with water.
- the aqueous phase was extracted several times with dichloromethane.
- the combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure.
- 2,2,6-Trimethylcyclohexanone 200 mg, 1 .43 mmol was dissolved in a round bottom flask under argon in abs. Tetra hydrofu ran (3 ml) and added dropwise to a solution of a Lithiumacetylid-ethylenediamine complex (171 mg, 1 .85 mmol, 85% content) in abs. Tetrahydrofuran (20 ml). After the addition had taken place, the reaction solution was stirred for 2 hours at room temperature, then treated with water and taken under concentrated reduced pressure. The remaining residue was mixed with water and dichloromethane and the aqueous phase extracted several times with dichloromethane. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure.
- reaction mixture was stirred for 4 h at room temperature and then treated with water.
- the aqueous phase was extracted several times with dichloromethane.
- the combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure.
- Diastereomer 2 - H-NMR (600 MHz, d 6 - DMSO ⁇ , ppm) 7.82 (d, 1 H), 7.58 (d, 1 H), 7.56 (dd, 1 H), 7.47 (dd 1 H), 4.84 (br, S, 1H, OH).
- 2,6-Dimethylcyclohexanone (1500 mg, 1.176 mmol) was dissolved in a round bottom flask under argon in abs. Tetrahydrofuran (5 ml) was dissolved and added dropwise to a solution of a Lithiumacetylid-ethylenediamine complex (1760 mg, 15.29 mmol, 80% content) in abs. Tetrahydrofuran (10 ml) was added. The reaction solution was stirred for 2 h after the addition at room temperature, then treated with water and concentrated under reduced pressure. The remaining residue was mixed with water and dichloromethane and the aqueous phase extracted several times with dichloromethane. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure.
- reaction mixture was stirred for 4 h at room temperature and then with
- Reaction product methyl-2 - [(1-hydroxy-2,6-dimethylcyclohexyl) ethynyl] benzoate are obtained as a mixture of diastereomers (170 mg, 57% of theory) and then the two diastereomers are separated by a new column chromatographic separation.
- Diastereomer 1-H-NMR 400 MHz, CDCb ⁇ , ppm) 7.72 (s, 1H), 7.41 (d, 1H), 7.23 (m, 1H), 3.90 (s, 3H), 2.38 (s, 3H ), 1.75 (m, 3H), 1.50 (m, 3H), 1.36 (m, 2H), 1.18 (d, 6H); Diastereomer 2 - H-NMR (400 MHz, CDCb ⁇ , ppm) 7.72 (s, 1H), 7.43 (d, 1H), 7.24 (m, 1H), 3.90 (s, 3H), 2.38 (s, 3H ), 1.63 (m, 3H), 1.50-1.30 (m, 5H), 1.14 (m, 6H).
- Example No.1.15-9 Example No.1.15-9:
- a further subject of the present invention is a spray solution for the treatment of plants, comprising an amount of at least one effective for increasing the resistance of plants to abiotic stress factors
- abscisic acid simultaneously with inventively substituted 1- (arylethynyl) -, 1- (heteroarylethynyl) -, 1- (heterocyclylethynyl) - and 1- (cycloalkenylethynyl) cyclohexanols of the general formula (I) for example in the context of the admixing of abscisic acid is preferably carried out in a dosage between 0.0001 and 3 kg / ha, more preferably between 0.001 and 2 kg / ha, particularly preferably between 0.005 and 1 kg / ha, in particular preferably between 0.006 and 0.25 kg / ha.
- the term resistance or resistance to abiotic stress is understood to mean various advantages for plants. Such advantageous properties are manifested, for example, in the following improved plant characteristics: improved root growth in terms of surface area and depth, increased lagging or tillering, stronger and more productive shoots and tillers,
- Photosynthesis beneficial plant properties, such as acceleration of maturation, more uniform maturity, greater attraction for Beneficials, improved pollination, or other benefits well known to those skilled in the art.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Pest Control & Pesticides (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyrrole Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Epoxy Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
The invention relates to the use of substituted 1-(aryl ethynyl)-, 1- (heteroaryl ethynyl)-, 1-(heterocyclyl ethynyl)- and 1-(cyloalkenyl ethynyl)-cyclohexanols or salts thereof. The groups in general formula (I) correspond to the definitions cited in the description, for increasing the stress tolerance in plants with respect to abiotic stress and/or for increasing plant yield.
Description
Verwendung substituierter 1 -(Arylethinyl)-, l -(Heteroarylethinyl)-, 1 - (Heterocyclyiethinyl)- und 1-(Cyloalkenylethinyl)-cyciohexanole als Wirkstoffe gegen abiotischen Pflanzenstress Use of substituted 1 - (arylethynyl) -, 1 - (heteroarylethynyl) -, 1 - (heterocycliciethynyl) - and 1- (cycloalkenylethynyl) cyclohexanols as active substances against abiotic plant stress
Beschreibung Die Erfindung betrifft die Verwendung substituierter 1 -(Arylethinyl)-, 1 -Description The invention relates to the use of substituted 1 - (arylethynyl) -, 1 -
(Heteroarylethinyl)-, 1 -(Heterocyclyiethinyl)- und 1 -(Cyloalkenylethinyl)-cyclohexanole oder deren Salze zur Steigerung der Stresstoleranz in Pflanzen gegenüber (Heteroarylethynyl) -, 1 - (Heterocyclyiethinyl) - and 1 - (cycloalkenylethynyl) cyclohexanols or salts thereof to increase the stress tolerance in plants
abiotischem Stress und/oder zur Erhöhung des Pflanzenertrags. Es ist bekannt, dass bestimmte 5-(1 .2-Epoxy-2,6,6-trimethylcyclohexyl)-3-methylpenta- 2,4-diensäuren und ihre Derivate Eigenschaften besitzen, die den Pflanzenwuchs beeinflussen (vgl. NL681 1769, DE1953152). Die Verwendung von 3-Methyl-5-(1 - hydroxy-2,2.6-trimethylcyclohexyl)-2-cis-4-trans-pentadiensäuremethylester gegen Frostschäden bei japanischen Dattelpflaumbäumen, Trauben und Maulbeeren wird ebenfalls in DE1953152 beschrieben. Die Verwendung von substituierten 5-Cyclohex- 2-en-1 -yl-penta-2.4-dienyl- und 5-Cyclohex-2-en-1 -yl-pent-2-en-4-inyl-olen, -thioethern und aminen als Inhibitoren der Epoxycarotenoiddioxygenase und als abiotic stress and / or to increase plant yield. It is known that certain 5- (1, 2-epoxy-2,6,6-trimethylcyclohexyl) -3-methylpenta-2,4-dienoic acids and their derivatives have properties which influence plant growth (see NL681 1769, DE1953152 ). The use of 3-methyl-5- (1-hydroxy-2,2,6-trimethylcyclohexyl) -2-cis-4-trans-pentadienoic acid methyl ester against frost damage in Japanese persimmon trees, grapes and mulberries is also described in DE1953152. The use of substituted 5-cyclohex-2-en-1 -yl-penta-2,4-dienyl and 5-cyclohex-2-en-1-yl-pent-2-en-4-ynyl-ols, thioethers and amines as inhibitors of Epoxycarotenoiddioxygenase and as
Keimungsinhibitoren wird in US2010/0160166 beschrieben. Es ist ebenfalls bekannt, daß (2Z,4E)-5-[(1 S,6S)-1-Hydroxy-2,2,6-trimethylcyclohexyl]penta-2,4-diensäure und (2Z,4E)-5-[(1 R.6R)-1 -Hydroxy-2.2,6-trimethylcyclohexyl]penta-2,4-diensäure mit Cytochrom P707A interagieren (vgl. Current Med. Chem. 2010, 17, 3230). Germination inhibitors are described in US2010 / 0160166. It is also known that (2Z, 4E) -5 - [(1S, 6S) -1-hydroxy-2,2,6-trimethylcyclohexyl] penta-2,4-dienoic acid and (2Z, 4E) -5- [(1R.6R) -1 -Hydroxy-2,2,6-trimethylcyclohexyl] penta-2,4-dienoic acid interact with cytochrome P707A (see Current Med. Chem., 2010, 17, 3230).
Abscisinsäureanaloga, in denen die Rotation einer der beiden Doppelbindungen durch ein aromatisches System eingeschränkt ist, werden in Agric. & Biol. Chem. Jap. Soc. Bioscience, Biotechnol. Agrochem. 1986, 50, 1097 beschrieben. Abscisic acid analogs, in which the rotation of one of the two double bonds by an aromatic system is restricted, are described in Agric. & Biol. Chem. Jap. Soc. Bioscience, Biotechnol. Agrochem. 1986, 50, 1097.
Es ist ebenfalls bekannt, daß substituierte 1 -(Phenylethinyl)-cyclohexanole mit bestimmten Substituentengruppen in der meta-Position des Phenylrestes als It is also known that substituted 1 - (phenylethynyl) cyclohexanols with certain substituent groups in the meta position of the phenyl radical as
Wirkstoffe in der Augenheilkunde verwendet werden können (vgl. WO2009005794, WO2009058216). Weiterhin ist die Herstellung von bestimmten substituierten 1 - (Phenylethinyl)-cyclohexanolen beschrieben, z. B. 1 -[(4-Methoxyphenyl)ethinyl]-2.2,6-
trimethylcyclohexanol und 1 -[(3-lsopropyl-4-methoxyphenyl)ethinyl]-2,2,6- trimethylcyclohexanol (vgl. Bioorg. Med. Chem. 2007, 15, 2736), 2-Methyl-1- (phenylethinyl)cyclohexanol (Org. Lett. 2005, 7, 1363), 1 -[(3-Methoxyphenyl)ethinyl]- 2,6-dimethylcyclohexanol und 1 -(Phenylethinyl)-2,6-dimethylcyclo-hexanol (Can. J. Chem. 1973, 51 , 3620), Ethyl-2-hydroxy-1 ,3-dimethyl-2-Active ingredients in ophthalmology can be used (see WO2009005794, WO2009058216). Furthermore, the preparation of certain substituted 1- (phenylethynyl) cyclohexanols is described, for. Eg 1 - [(4-methoxyphenyl) ethynyl] -2.2,6- trimethylcyclohexanol and 1 - [(3-isopropyl-4-methoxyphenyl) ethynyl] -2,2,6-trimethylcyclohexanol (see Bioorg Med Med Chem., 2007, 15, 2736), 2-methyl-1- (phenylethynyl) cyclohexanol (Org. Lett. 2005, 7, 1363), 1 - [(3-methoxyphenyl) ethynyl] -2,6-dimethylcyclohexanol and 1- (phenylethynyl) -2,6-dimethylcyclohexanol (Can. J. Chem , 51, 3620), ethyl 2-hydroxy-1,3-dimethyl-2-
(phenylethinyl)cyclohexancarboxylat und Ethyl-2-hydroxy-2-[(3- isopropylphenyl)ethinyl]-1 .3-dimethylcyclohexancarboxylat (J. Am. Chem. Soc. 1954, 76, 5380; Synlett 2005, 2919). Von den erfindungsgemäßen substituierten l-(Arylethinyl)-, 1 -(Heteroarylethinyl)-, 1 - (Heterocyclylethinyl)- und 1-(Cyloalkenylethinyl)-cyclohexanolen ist dagegen die Verwendung zur Steigerung der Stresstoleranz in Pflanzen gegenüber abiotischem Stress, zur Stärkung des Pflanzenwachstums und/oder zur Erhöhung des (phenylethynyl) cyclohexanecarboxylate and ethyl 2-hydroxy-2 - [(3-isopropylphenyl) ethynyl] -1,3-dimethylcyclohexanecarboxylate (J. Am. Chem. Soc. 1954, 76, 5380, Synlett 2005, 2919). By contrast, the substituted l- (arylethynyl) -, 1- (heteroarylethynyl) -, 1- (heterocyclylethynyl) - and 1- (cycloalkenylethynyl) -cyclohexanols according to the invention represent the use for increasing the stress tolerance in plants to abiotic stress, for strengthening plant growth and / or to increase the
Pflanzenertrags nicht beschrieben. Plant yield not described.
Es ist bekannt, dass Pflanzen auf natürliche Stressbedingungen, wie beispielsweise Kälte, Hitze, Trockenstress (Stress verursacht durch Trockenheit und/oder It is known that plants are susceptible to natural stress conditions such as cold, heat, drought stress (stress caused by dryness and / or
Wassermangel), Verwundung, Pathogenbefall (Viren, Bakterien, Pilze, Insekten) etc. aber auch auf Herbizide mit spezifischen oder unspezifischen Abwehrmechanismen reagieren können [Pflanzenbiochemie, S. 393-462 , Spektrum Akademischer Verlag, Heidelberg, Berlin, Oxford, Hans W. Heidt, 1996.; Biochemistry and Molecular Biology of Plants, S. 1 102-1203, American Society of Plant Physiologists, Rockviiie, Maryland, eds. Buchanan, Gruissem, Jones, 2000]. In Pflanzen sind zahlreiche Proteine und die sie codierenden Gene bekannt, die an Abwehrreaktionen gegen abiotischen Stress (z.B. Kälte, Hitze, Trockstress, Salz, Überflutung) beteiligt sind. Diese gehören teilweise zu Signaltransduktionsketten (z.B. Transkriptionsfaktoren, Kinasen, Phosphatasen) oder bewirken eine physiologische Antwort der Pflanzenzelle (z.B. lonentransport, Entgiftung reaktiver Sauerstoff- Spezies). Zu den Signalkettengenen der abiotischen Stressreaktion gehören u.a. Transkriptionsfaktoren der Klassen DREB und CBF (Jaglo-Ottosen et al., 1998, Science 280; 104-106). An der Reaktion auf Salzstress sind Phosphatasen vom Typ ATPK und MP2C beteiligt. Ferner wird bei Salzstress häufig die Biosynthese von Osmolyten wie Prolin oder Sucrose aktiviert. Beteiligt sind hier z.B. die Sucrose-
Synthase und Prolin-Transporter (Hasegawa et al., 2000, Annu Rev Plant Physiol Plant Mol Biol 51 : 463-499). Die Stressabwehr der Pflanzen gegen Kälte und Lack of water), wounding, pathogen infestation (viruses, bacteria, fungi, insects) etc. but also can react to herbicides with specific or nonspecific defense mechanisms [Plant Biochemistry, pp. 393-462, Spektrum Akademischer Verlag, Heidelberg, Berlin, Oxford, Hans W. Heidt, 1996; Biochemistry and Molecular Biology of Plants, p. 1 102-1203, American Society of Plant Physiologists, Rockviie, Maryland, eds. Buchanan, Gruissem, Jones, 2000]. In plants numerous proteins and their coding genes are known, which are involved in defense reactions against abiotic stress (eg cold, heat, dry stress, salt, flooding). These belong in part to signal transduction chains (eg transcription factors, kinases, phosphatases) or cause a physiological response of the plant cell (eg ion transport, detoxification of reactive oxygen species). The signal chain genes of the abiotic stress reaction include transcription factors of the classes DREB and CBF (Jaglo-Ottosen et al., 1998, Science 280; 104-106). The response to salt stress involves phosphatases of the ATPK and MP2C types. Furthermore, in salt stress the biosynthesis of osmolytes such as proline or sucrose is often activated. For example, the sucrose Synthase and proline transporters (Hasegawa et al., 2000, Annu Rev Plant Physiol Plant Mol Biol 51: 463-499). The stress control of plants against cold and
Trockenheit benutzt z.T. die gleichen molekularen Mechanismen. Bekannt ist die Akkumulation von sogenannten Late Embryogenesis Abundant Proteins (LEA- Proteine), zu denen als wichtige Klasse die Dehydrine gehören (Ingram and Bartels, 1996, Annu Rev Plant Physiol Plant Mol Biol 47: 277-403, Close, 1997, Physiol Plant 100: 291 -296). Es handelt sich dabei um Chaperone, die Vesikel, Proteine und Membranstrukturen in gestressten Pflanzen stabilisieren (Bray, 1993, Plant Physiol 103: 1035-1040). Außerdem erfolgt häufig eine Induktion von Aldehyd- Deydrogenasen, welche die bei oxidativem Stress entstehenden reaktiven Sauerstoff- Spezies (ROS) entgiften (Kirch et al., 2005, Plant Mol Biol 57: 315-332). Dryness used z.T. the same molecular mechanisms. The accumulation of so-called Late Embryogenesis Abundant Proteins (LEA proteins), which include dehydrins as an important class, is known (Ingram and Bartels, 1996, Annu Rev Plant Physiol Plant Mol Biol 47: 277-403, Close, 1997, Physiol Plant 100: 291-296). These are chaperones that stabilize vesicles, proteins and membrane structures in stressed plants (Bray, 1993, Plant Physiol 103: 1035-1040). Moreover, induction of aldehyde dehydrogenases, which detoxify the reactive oxygen species (ROS) produced by oxidative stress, is often used (Kirch et al., 2005, Plant Mol Biol 57: 315-332).
Heat Shock Faktoren (HSF) und Heat Shock Proteine (HSP) werden bei Hitzestress aktiviert und spielen hier als Chaperone eine ähnliche Rolle wie die Dehydrine bei Kälte- und Trockenstress (Yu et al., 2005, Mol Cells 19: 328-333). Heat Shock Factors (HSF) and Heat Shock Proteins (HSP) are activated by heat stress and act as chaperones in a similar role to dehydrins in cold and dry stress (Yu et al., 2005, Mol Cells 19: 328-333).
Eine Reihe von pflanzenendogenen Signalstoffen, die in die Stresstoleranz bzw. die Pathogenabwehr involviert sind, sind bereits bekannt. Zu nennen sind hier A number of plant endogenous signaling substances involved in stress tolerance and pathogen defense are already known. To call here are
beispielsweise Salicylsäure, Benzoesäure, Jasmonsäure oder Ethylen [Biochemistry and Molecular Biology of Plants, S. 850-929, American Society of Plant Physiologists, Rockville, Maryland, eds. Buchanan, Gruissem, Jones, 2000]. Einige dieser for example, salicylic acid, benzoic acid, jasmonic acid or ethylene [Biochemistry and Molecular Biology of Plants, pp. 850-929, American Society of Plant Physiologists, Rockville, Maryland, eds. Buchanan, Gruissem, Jones, 2000]. Some of these
Substanzen oder deren stabile synthetische Derivate und abgeleitete Strukturen sind auch bei externer Applikation auf Pflanzen oder Saatgutbeizung wirksam und aktivieren Abwehrreaktionen, die eine erhöhte Stress- bzw. Pathogentoleranz der Pflanze zur Folge haben [Sembdner, and Parthier, 1993, Ann. Rev. Plant Physiol. Plant Mol. Biol. 44: 569-589]. Substances or their stable synthetic derivatives and derived structures are also effective in external application to plants or seed dressing and activate defense reactions that result in an increased stress or pathogen tolerance of the plant [Sembdner, and Parthier, 1993, Ann. Rev. Plant Physiol. Plant Mol. Biol. 44: 569-589].
Es ist weiter bekannt, dass chemische Substanzen die Toleranz von Pflanzen gegen abioti sehen Stress erhöhen können. Derartige Substanzen werden dabei entweder durch Saatgut-Beizung, durch Blattspritzung oder durch Bodenbehandung appliziert. So wird eine Erhöhung der abioti sehen Stresstoleranz von Kulturpflanzen durch Behandlung mit Elicitoren der Systemic Acquired Resistance (SAR) oder It is also known that chemical substances can increase the tolerance of plants to abiotic stress. Such substances are applied either by seed dressing, by foliar spraying or by soil treatment. Thus, an increase in the abioti stress tolerance of crops by treatment with systemic acquired resistance (SAR) or elicitors
Abscisinsäure-Derivaten beschrieben (Schading and Wei, WO200028055; Churchill et al., 1998, Plant Growth Regul 25: 35-45). Desweiteren wurden Effekte von Abscisic acid derivatives (Schading and Wei, WO200028055, Churchill et al., 1998, Plant Growth Regul 25: 35-45). Furthermore, effects of
Wachstumsregulatoren auf die Stresstoleranz von Kulturpflanzen beschrieben
(Morrison and Andrews, 1992, J Plant Growth Regul 1 1 : 1 13-1 17, RD-259027). In diesem Zusammenhang ist ebenfalls bekannt, dass ein wachstumsregulierendes Naphthylsulfonamid (4-Brom-N-(pyhdin-2-ylmethyl)naphthalin-1 -Sulfonamid) die Keimung von Pflanzensamen in der gleichen Weise wie Abscisinsäure beeinflusst (Park et al. Science 2009, 324, 1068-1071 ). Außerdem ist bekannt, dass ein weiteres Naphthylsulfonamid, N-(6-aminohexyl)-5-chlornaphthalin-1 -Sulfonamid, den Calcium- Spiegel in Pflanzen beeinflusst, die einem Kälteschock ausgesetzt wurden (Cholewa et al. Can. J. Botany 1997, 75, 375-382). Auch bei Anwendung von Fungiziden, insbesondere aus der Gruppe der Strobilurine oder der Succinat Dehydrogenase Inhibitoren werden ähnliche Effekte beobachtet, die häufig auch mit einer Ertragssteigerung einhergehen (Draber et al., DE3534948, Bartlett et al., 2002, Pest Manag Sei 60: 309). Es ist ebenfalls bekannt, dass das Herbizid Glyphosat in niedriger Dosierung das Wachstum einiger Pflanzenarten stimuliert (Cedergreen, Env. Pollution 2008, 156, 1099). Growth regulators described on the stress tolerance of crops (Morrison and Andrews, 1992, J Plant Growth Regul 1 1: 1 13-1 17, RD-259027). In this connection, it is also known that a growth-regulating naphthylsulfonamide (4-bromo-N- (pyhdin-2-ylmethyl) naphthalene-1-sulfonamide) influences the germination of plant seeds in the same manner as abscisic acid (Park et al., Science 2009, 324, 1068-1071). In addition, it is known that another naphthylsulfonamide, N- (6-aminohexyl) -5-chloronaphthalene-1-sulfonamide, affects calcium levels in plants that have been cold shocked (Cholewa et al., Can. J. Botany 1997, Vol. 75, 375-382). Similar effects are observed even when using fungicides, in particular from the group of strobilurins or succinate dehydrogenase inhibitors, which are often accompanied by an increase in yield (Draber et al., DE3534948, Bartlett et al., 2002, Pest Management, 60: 309 ). It is also known that the low dose herbicide glyphosate stimulates the growth of some plant species (Cedergreen, Env. Pollution 2008, 156, 1099).
Bei osmotischem Stress ist eine Schutzwirkung durch Applikation von Osmolyten wie z.B. Glycinbetain oder deren biochemischen Vorstufen, z.B. Cholin-Derivate At osmotic stress, a protective effect is provided by the application of osmolytes, e.g. Glycine betaine or its biochemical precursors, e.g. Choline derivatives
beobachtet worden (Chen et al., 2000, Plant Cell Environ 23: 609-618, Bergmann et al., DE4103253). Auch die Wirkung von Antioxidantien wie z.B Naphtole und Xanthine zur Erhöhung der abiotischen Stresstoleranz in Pflanzen wurde bereits beschrieben (Bergmann et al., DD277832, Bergmann et al., DD277835). Die molekularen Ursachen der Anti-Stress-Wirkung dieser Substanzen sind jedoch weitgehend unbekannt. Es ist weiter bekannt, dass die Toleranz von Pflanzen gegenüber abiotischem Stress durch eine Modifikation der Aktivität von endogenen Poly-ADP-ribose Polymerasen (PARP) oder Poly-(ADP-ribose) glycohydrolasen (PARG) erhöht werden kann (de Block et al., The Plant Journal, 2004, 41 , 95; Levine et al., FEBS Lett. 1998, 440, 1 ; WO0004173; WO04090140). (Chen et al., 2000, Plant Cell Environ 23: 609-618, Bergmann et al., DE4103253). The action of antioxidants such as naphtols and xanthines to increase the abiotic stress tolerance in plants has also been described (Bergmann et al., DD277832, Bergmann et al., DD277835). However, the molecular causes of the anti-stress effects of these substances are largely unknown. It is further known that the tolerance of plants to abiotic stress can be increased by a modification of the activity of endogenous poly-ADP-ribose polymerases (PARP) or poly (ADP-ribose) glycohydrolases (PARG) (de Block et al. , The Plant Journal, 2004, 41, 95; Levine et al., FEBS Lett. 1998, 440, 1, WO0004173, WO04090140).
Somit ist bekannt, dass Pflanzen über mehrere endogene Reaktionsmechanismen verfügen, die eine wirksame Abwehr gegenüber verschiedensten Schadorganismen und/oder natürlichem abiotischem Stress bewirken können.
Da sich die ökologischen und ökonomischen Anforderungen an moderne Thus, it is known that plants have several endogenous reaction mechanisms that can effectively prevent various harmful organisms and / or natural abiotic stress. As the environmental and economic demands on modern
Pflanzenbehandlungsmittel laufend erhöhen, beispielsweise was Toxizität, Selektivität, Aufwandmenge, Rückstandsbildung und günstige Herstellbarkeit angeht, besteht die ständige Aufgabe, neue Pflanzenbehandlungsmittel zu entwickeln, die zumindest in Teilbereichen Vorteile gegenüber den bekannten aufweisen. Constantly increase plant treatment, for example, as regards toxicity, selectivity, application rate, residue formation and cheap manufacturability, there is the constant task of developing new plant treatment agents that have advantages over the known at least in some areas.
Daher bestand die Aufgabe der vorliegenden Erfindung darin, weitere Verbindungen bereitzustellen, die die Toleranz gegenüber abiotischem Stress in Pflanzen erhöhen, insbesondere eine Stärkung des Pflanzenwachstums bewirken und/oder zur Erhöhung des Pflanzenertrags beitragen. Therefore, the object of the present invention was to provide further compounds which increase the tolerance to abiotic stress in plants, in particular to effect a strengthening of plant growth and / or contribute to increasing the plant yield.
Gegenstand der vorliegenden Erfindung ist demnach die Verwendung substituierter 1 - (Arylethinyl)-, 1 -(Heteroarylethinyl)-, l -(Heterocyclylethinyl)- und 1 -(Cyloalkenylethinyl)- cyclohexanole der allgemeinen Formel (I) oder deren Salze zur Erhöhung der The present invention accordingly provides the use of substituted 1 - (arylethynyl) -, 1 - (heteroarylethynyl) -, l - (heterocyclylethynyl) - and 1 - (cycloalkenylethynyl) - cyclohexanols of the general formula (I) or salts thereof for increasing the
Stresstoleranz in Pflanzen gegenüber abiotischem Stress und/oder zur Erhöhung des Pflanzenertrags. Stress tolerance in plants to abiotic stress and / or to increase plant yield.
wobei in which
[X-Y] für die Gruppierungen [X-Y] for the groupings
Q für die Gruppierungen Q-1 bis Q-6
Q for the groupings Q-1 to Q-6
Q-1 Q-2 Q-3 Q-1 Q-2 Q-3
steht, wobei R7, R8, R9, R10, R11, R12, R13, R14. R17, R18, R19, R20, R22, R23, R24, R25, R26, R28, R29 und R30 und A1 bis A9 jeweils die Bedeutung gemäß der nachstehenden Definitionen haben und wobei der Pfeil für eine Bindung zur jeweiligen Gruppierung C-R6 in der allgemeinen Formel (I) steht, wherein R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 . R 17 , R 18 , R 19 , R 20 , R 22 , R 23 , R 24 , R 25 , R 26 , R 28 , R 29 and R 30 and A 1 to A 9 each have the meaning as defined below, and wherein the arrow represents a bond to the respective grouping CR 6 in the general formula (I),
R1 für Alkyl, Cycioaikyl, Cycloalkenyl, Alkenyl, Alkinyl, Alkenylalkyl, Alkinylalkyl, Aikoxyalkyi, Hydroxyalkyl, Haloalkyl, Haloaikenyi, Haloalkinyi, Haioalkoxyalkyl, Alkoxyhaloalkyl, Haloalkoxyhaloalkyl, Alkylthioalkyl, Haloalkylthioalkyl, Aryl, Heteroaryl, Heterocyclyl steht, R 1 is alkyl, cycioalkyl, cycloalkenyl, alkenyl, alkynyl, alkenylalkyl, alkynylalkyl, aikoxyalkyl, hydroxyalkyl, haloalkyl, haloalkyl, haloalkynyl, haloalkoxyalkyl, alkoxyhaloalkyl, haloalkoxyhaloalkyl, alkylthioalkyl, haloalkylthioalkyl, aryl, heteroaryl, heterocyclyl,
R2, R3 und R4 unabhängig voneinander für Wasserstoff, Halogen, Alkyl, Cycioaikyl, Cycloalkenyl, Alkenyl, Alkinyl, Alkenylalkyl, Alkinylalkyl, Aikoxyalkyi, R 2 , R 3 and R 4 independently of one another are hydrogen, halogen, alkyl, cycioalkyl, cycloalkenyl, alkenyl, alkynyl, alkenylalkyl, alkynylalkyl, aikoxyalkyi,
Hydroxyalkyl, Haloalkyl, Haloaikenyi, Haloalkinyi, Haioalkoxyalkyl, Hydroxyalkyl, haloalkyl, haloaikenyi, haloalkinyi, haloalkoxyalkyl,
Alkoxyhaloalkyl, Haloalkoxyhaloalkyl, Alkylthioalkyl, Haloalkylthioalkyl, Aryl, Heteroaryl, Heterocyclyl stehen, Alkoxyhaloalkyl, haloalkoxyhaloalkyl, alkylthioalkyl, haloalkylthioalkyl, aryl, heteroaryl, heterocyclyl,
R5 für Hydroxy, Alkoxy, Aryloxy, Cycloalkyloxy, Alkenyloxy, Alkenylalkyloxy, R 5 is hydroxy, alkoxy, aryloxy, cycloalkyloxy, alkenyloxy, alkenylalkyloxy,
Alkoxyalkyloxy, Alkylcarbonyloxy, Arylcarbonyloxy, Heteroarylcarbonyloxy, Cycloalkylcarbonyloxy, Alkoxycarbonyloxy, Allyloxycarbonyloxy, Alkoxyalkyloxy, alkylcarbonyloxy, arylcarbonyloxy, heteroarylcarbonyloxy, cycloalkylcarbonyloxy, alkoxycarbonyloxy, allyloxycarbonyloxy,
Aryloxyalkyloxy, Arylalkyloxy, Alkoxyalkoxyalkyloxy, Alkylthioalkyloxy, Aryloxyalkyloxy, arylalkyloxy, alkoxyalkoxyalkyloxy, alkylthioalkyloxy,
Trialkylsilyloxy, Alkyl(Bis-alkyl)silyloxy, Alkyl(Bis-Aryl)silyloxy, Aryl(Bis- alkyl)silyloxy, Cycloalkyl(Bis-alkyl)silyloxy, Halo(Bis-alkyl)silyloxy, Trialkylsilyloxy, alkyl (bis-alkyl) silyloxy, alkyl (bis-aryl) silyloxy, aryl (bis-alkyl) silyloxy, cycloalkyl (bis-alkyl) silyloxy, halo (bis-alkyl) silyloxy,
Trialkylsilylalkoxyalkyloxy, steht,
für Nitro, Amino, Hydroxy, Hydrothio, Thiocyanato, Isothiocyanato, Halogen, Alkyl, Cycloalkyl, Alkenyl, Cycloalkenyl, Alkinyl, Arylalkinyl, Trialkylsilylalkinyl, Aryl, Arylalkyl, Arylalkoxy, Heteroaryl, Haloalkyl, Halocycloalkyl, Haloalkenyl, Alkoxy, Haloalkoxy, Aryloxy, Heteroaryloxy, Cycloalkyloxy, Cycloalkylalkoxy, Alkenyloxy, Alkinylalkyloxy, Hydroxyalkyl, Alkoxyalkyl, Aryloxyalkyl, Trialkylsilylalkoxyalkyloxy, for nitro, amino, hydroxy, hydrothio, thiocyanato, isothiocyanato, halogen, alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, arylalkynyl, trialkylsilylalkynyl, aryl, arylalkyl, arylalkoxy, heteroaryl, haloalkyl, halocycloalkyl, haloalkenyl, alkoxy, haloalkoxy, aryloxy, heteroaryloxy , Cycloalkyloxy, cycloalkylalkoxy, alkenyloxy, alkynylalkyloxy, hydroxyalkyl, alkoxyalkyl, aryloxyalkyl,
Heteroaryloxyalkyl, Alkylthio, Haloalkylthio, Alkoxycarbonylalkylthio, Arylthio, Cycloalkylthio, Heteroarylthio, Alkylthioalkyi, Alkylamino, Bisalkylamino, Alkenylamino, Cycloalkylamino, Alkylcarbonylamino, Cycloalkylcarbonylamino, Arylcarbonylamino, Heteroarylcarbonylamino, Formylamino, Hetaryloxyalkyl
Haloalkylcarbonylamino, Alkoxy carbonylamino, Alkylaminocarbonylamino, Alkyl(Alkyl-)aminocarbonylamino, Alkylsulfonylamino, Cycloalkylsuifonylamino, Arylsulfonylamino, Hetarylsulfonylamino, Sulfonylhaloalkylamino, Haloalkylcarbonylamino, alkoxycarbonylamino, alkylaminocarbonylamino, alkyl (alkyl) aminocarbonylamino, alkylsulfonylamino, cycloalkylsulfonylamino, arylsulfonylamino, hetarylsulfonylamino, sulfonylhaloalkylamino,
Aminoaikylsulfonyl, Aminohaioalkyisulfonyl, Alkylaminosulfonyl, Aminosulfonyl, Bisalkylaminosulfonyl, Cycloalkylaminosulfonyl, Haloalkylaminosulfonyl, Heteroarylaminosulfonyl, Arylaminosulfonyl, Arylalkylaminosulfonyl, Amino-alkylsulfonyl, amino-halo-alkylsulfonyl, alkylaminosulfonyl, aminosulfonyl, bisalkylaminosulfonyl, cycloalkylaminosulfonyl, haloalkylaminosulfonyl, heteroarylaminosulfonyl, arylaminosulfonyl, arylalkylaminosulfonyl,
Alkylsulfonyl, Cycloalkylsulfonyl, Arylsulfonyl, Alkylsulfinyl, Cycloalkylsulfinyl, Arylsulfinyl, N,S-Dialkylsulfonimidoyl, S-Alkylsulfonimidoyl, Alkylsulfonyl, cycloalkylsulfonyl, arylsulfonyl, alkylsulfinyl, cycloalkylsulfinyl, arylsulfinyl, N, S-dialkylsulfonimidoyl, S-alkylsulfonimidoyl,
Alkylsulfonylaminocarbonyl, Cycloalkylsulfonylaminocarbonyl, Alkylsulfonylaminocarbonyl, cycloalkylsulfonylaminocarbonyl,
Arylalkylcarbonylamino, Cycloalkylalkylcarbonylamino, Arylalkylcarbonylamino, cycloalkylalkylcarbonylamino,
Heteroarylcarbonylamino, Alkoxyalkylcarbonylamino, Heteroarylcarbonylamino, alkoxyalkylcarbonylamino,
Hydroxyalkylcarbonylamino, Alkoxycarbonylaminoalkylcarbonylamino, Cyano, Cyanoalkyl, Hydroxycarbonyl, Alkoxycarbonyl, Cycloalkoxycarbonyl, Hydroxyalkylcarbonylamino, alkoxycarbonylaminoalkylcarbonylamino, cyano, cyanoalkyl, hydroxycarbonyl, alkoxycarbonyl, cycloalkoxycarbonyl,
Cycloalkylalkoxycarbonyl, Aryloxycarbonyl, Arylalkoxycarbonyl, Cycloalkylalkoxycarbonyl, aryloxycarbonyl, arylalkoxycarbonyl,
Alkenyloxycarbonyl, Alkinyloxycarbonyl, Haloalkyloxycarbonyl, Alkenyloxycarbonyl, alkynyloxycarbonyl, haloalkyloxycarbonyl,
Alkoxyalkoxycarbonyl, Alkenyloxyalkoxycarbonyl, Alkylaminoalkoxycarbonyl, Trisalkylsilyloxyalkoxycarbonyl, Bis-Alkylaminoalkoxycarbonyl, Alkoxyalkoxycarbonyl, alkenyloxyalkoxycarbonyl, alkylaminoalkoxycarbonyl, trisalkylsilyloxyalkoxycarbonyl, bis-alkylaminoalkoxycarbonyl,
Alkyl(alkyl)aminoalkoxycarbonyl, Cyanoalkoxycarbonyl, Heterocyclyl-N- alkoxycarbonyl, Heteroaryloxy carbonyl, Heteroarylalkoxycarbonyl, Alkyl (alkyl) aminoalkoxycarbonyl, cyanoalkoxycarbonyl, heterocyclyl-N-alkoxycarbonyl, heteroaryloxycarbonyl, heteroarylalkoxycarbonyl,
Heterocyclylalkoxycarbonyl, Heterocyclyloxycarbonyl, Alkenylalkoxycarbonyl, Alkinylalkoxycarbonyl, Arylalkinyloxycarbonyl, Arylalkenyloxycarbonyl, Heterocyclylalkoxycarbonyl, heterocyclyloxycarbonyl, alkenylalkoxycarbonyl, alkynylalkoxycarbonyl, arylalkynyloxycarbonyl, arylalkenyloxycarbonyl,
Aminocarbonyl, Alkylaminocarbonyl, Bisalkylaminocarbonyl, Aminocarbonyl, alkylaminocarbonyl, bisalkylaminocarbonyl,
Alkyl(Alkyl)aminocarbonyl, Alkyl(Alkoxy)aminocarbonyl, Alkyl (alkyl) aminocarbonyl, alkyl (alkoxy) aminocarbonyl,
Alkoxyalkylaminocarbonyl, Alkenylaminocarbonyl, Cycloalkylaminocarbonyl,
Arylaminocarbonyl, Arylalkylaminocarbonyl, Heteroarylalkylaminocarbonyl, Cyanoalkylaminocarbonyl, Haloalkylaminocarbonyl, Alkinylalkylaminocarbonyl, Alkoxycarbonylaminocarbonyl, Arylalkoxycarbonylaminocarbonyl, Alkoxyalkylaminocarbonyl, alkenylaminocarbonyl, cycloalkylaminocarbonyl, Arylaminocarbonyl, arylalkylaminocarbonyl, heteroarylalkylaminocarbonyl, cyanoalkylaminocarbonyl, haloalkylaminocarbonyl, alkynylalkylaminocarbonyl, alkoxycarbonylaminocarbonyl, arylalkoxycarbonylaminocarbonyl,
Hydroxycarbonylalkyl, Alkoxycarbonylalkyl, Cycloalkoxycarbonylalkyl, Hydroxycarbonylalkyl, alkoxycarbonylalkyl, cycloalkoxycarbonylalkyl,
Cycloalkylalkoxycarbonylalkyl, Alkenyloxycarbonylalkyl, Arylalkoxycarbonylalkyl,Cycloalkylalkoxycarbonylalkyl, alkenyloxycarbonylalkyl, arylalkoxycarbonylalkyl,
Alkylaminocarbonylalkyl, Aminocarbonylalkyl, Bisalkylaminocarbonylalkyl, Cycloalkylaminocarbonylalkyl, Arylalkylaminocarbonylalkyl, Alkylaminocarbonylalkyl, aminocarbonylalkyl, bisalkylaminocarbonylalkyl, cycloalkylaminocarbonylalkyl, arylalkylaminocarbonylalkyl,
Heteroarylalkylaminocarbonylalkyl, Cyanoalkylaminocarbonylalkyl, Heteroarylalkylaminocarbonylalkyl, cyanoalkylaminocarbonylalkyl,
Haloalkylaminocarbonylalkyl, Alkinylalkylaminocarbonylalkyl, Haloalkylaminocarbonylalkyl, alkynylalkylaminocarbonylalkyl,
Cycloalkylalkylaminocarbonylalkyl, Alkoxycarbonylaminocarbonylalkyl, Cycloalkylalkylaminocarbonylalkyl, alkoxycarbonylaminocarbonylalkyl,
Arylalkoxycarbonylaminocarbonylalkyl, Alkoxycarbonylalkylaminocarbonyl, Hydroxycarbonylalkylaminocarbonyl, Arylalkoxycarbonylalkylaminocarbonyl, Alkoxycarbonylheterocyclyl-N-carbonyl. Arylalkoxycarbonylaminocarbonylalkyl, alkoxycarbonylalkylaminocarbonyl, hydroxycarbonylalkylaminocarbonyl, arylalkoxycarbonylalkylaminocarbonyl, alkoxycarbonylheterocyclyl-N-carbonyl.
Alkoxycarbonylalkylheterocyclylidenaminocarbonyl, Alkoxycarbonylalkylheterocyclylidenaminocarbonyl,
Alkoxycarbonylheterocyclylidenalkylaminocarbonyl, Alkoxycarbonylheterocyclylidenalkylaminocarbonyl,
Alkoxycarbonylalkyl(alkyl)aminocarbonyl, Alkoxycarbonylalkyl (alkyl) aminocarbonyl,
Alkoxycarbonylcycloalkylidenaminocarbonyl, Heterocyclyl-N-carbonyl, Alkoxycarbonylcycloalkylidene-aminocarbonyl, heterocyclyl-N-carbonyl,
Aminocarbonylalkylaminocarbonyl, Alkylaminocarbonylalkylaminocarbonyl, Cycloalkylaminocarbonylalkylaminocarbonyl, Cycloalkylalkylaminocarbonyl, Cycloalkylalkylaminocarbonylalkyl, Aminocarbonylalkylaminocarbonyl, alkylaminocarbonylalkylaminocarbonyl, cycloalkylaminocarbonylalkylaminocarbonyl, cycloalkylalkylaminocarbonyl, cycloalkylalkylaminocarbonylalkyl,
Cycloalkylalkylaminocarbonylalkylaminocarbonyl, Alkenylalkylaminocarbonyl, Alkenylaminocarbonylalkyl, Alkenylalkylaminocarbonylalkyl, Alkylcarbonyl, Cycloalkylcarbonyl, Arylcarbonyl, Formyl, Hydroxyiminomethyl, Cycloalkylalkylaminocarbonylalkylaminocarbonyl, alkenylalkylaminocarbonyl, alkenylaminocarbonylalkyl, alkenylalkylaminocarbonylalkyl, alkylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, formyl, hydroxyiminomethyl,
Aminoiminomethyl, Alkoxyiminomethyl, Alkylaminoiminomethyl, Aminoiminomethyl, alkoxyiminomethyl, alkylaminoiminomethyl,
Dialkylaminoiminomethyl, Cycloalkoxyiminomethyl, Cycloalkylalkoximinomethyl,Dialkylaminoiminomethyl, cycloalkoxyiminomethyl, cycloalkylalkoximinomethyl,
Aryloximinomethyl, Arylalkoxyiminomethyl, Arylalkylaminoiminomethyl, Aryloximinomethyl, arylalkoxyiminomethyl, arylalkylaminoiminomethyl,
Alkenyloxyiminomethyl, Arylaminoiminomethyl, Arylsulfonylaminoiminomethyl, Heteroarylalkyl, Heterocyclylalkyl, Hydroxycarbonylheterocyclyl, Alkenyloxyiminomethyl, arylaminoiminomethyl, arylsulfonylaminoiminomethyl, heteroarylalkyl, heterocyclylalkyl, hydroxycarbonylheterocyclyl,
Alkoxycarbonylheterocyclyl, Alkenyloxycarbonylheterocyclyl, Alkoxycarbonylheterocyclyl, alkenyloxycarbonylheterocyclyl,
Alkenylalkoxycarbonylheterocyclyl, Arylalkoxycarbonylheterocyclyl, Alkenylalkoxycarbonylheterocyclyl, arylalkoxycarbonylheterocyclyl,
Cycloalkoxycarbonylheterocyclyl, Cycloalkylalkoxycarbonylheterocyclyl, Aminocarbonylheterocyclyl, Alkylaminocarbonylheterocyclyl, Bis- Alkylaminocarbonylheterocyclyl, Cycloalkylaminocarbonylheterocyclyl, Cycloalkoxycarbonylheterocyclyl, cycloalkylalkoxycarbonylheterocyclyl, aminocarbonylheterocyclyl, alkylaminocarbonylheterocyclyl, bis-alkylaminocarbonylheterocyclyl, cycloalkylaminocarbonylheterocyclyl,
Arylalkylaminocarbonylheterocyclyl, Alkenylaminocarbonylheterocyclyl,
Hydroxycarbonylheterocyclylalkyl, Alkoxycarbonylheterocyclylalkyl, Arylalkylaminocarbonylheterocyclyl, alkenylaminocarbonylheterocyclyl, Hydroxycarbonylheterocyclylalkyl, alkoxycarbonylheterocyclylalkyl,
Hydroxycarbonylcycloalkylalkyl, Alkoxycarbonylcycloalkylalkyl, Hydroxycarbonylcycloalkylalkyl, alkoxycarbonylcycloalkylalkyl,
Hydroxyaminocarbonyl, Alkoxyaminocarbonyl, Arylalkoxyaminocarbonyl, Heterocyclyl, Alkylcarbonyloxy, Arylcarbonyloxy, Heteroarylcarbonyloxy, Cycloalkylcarbonyloxy, Alkoxycarbonyloxy, Alkenyloxycarbonyloxy steht, Hydroxyaminocarbonyl, alkoxyaminocarbonyl, arylalkoxyaminocarbonyl, heterocyclyl, alkylcarbonyloxy, arylcarbonyloxy, heteroarylcarbonyloxy, cycloalkylcarbonyloxy, alkoxycarbonyloxy, alkenyloxycarbonyloxy,
R7, R8 , R9 und R10 unabhängig voneinander für Wasserstoff, Halogen, Nitro, Amino, Cyano, Alkyl, Aryl, Heteroaryl, Cycloalkyl, Cycloalkenyl, Alkenyl, Alkinyl, Alkenylalkyl, Alkinylalkyl, Hydroxy, Alkoxy, Alkoxyalkoxy, Alkoxyalkyl, R 7 , R 8 , R 9 and R 10 are each independently hydrogen, halogen, nitro, amino, cyano, alkyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl, alkenyl, alkynyl, alkenylalkyl, alkynylalkyl, hydroxy, alkoxy, alkoxyalkoxy, alkoxyalkyl,
Hydroxyalkyi, Haioalkoxy, Haloalkyl, Haloaikenyi, Haloalkinyl, Haloaikoxyalkyl, Alkoxyhaloalkyl, Haloalkoxyhaloalkyl, Hydrothio, Alkylthio, Haloalkylthio, Alkylthioalkyl, Haloalkylthioalkyl, Alkylamino, Bisalkylamino, Alkenylamino, Cycloalkylamino, Alkylcarbonylamino, Cycloalkylcarbonylamino, Hydroxyalkyl, haloalkoxy, haloalkyl, haloaikenyi, haloalkynyl, haloakoxyalkyl, alkoxyhaloalkyl, haloalkoxyhaloalkyl, hydrothio, alkylthio, haloalkylthio, alkylthioalkyl, haloalkylthioalkyl, alkylamino, bisalkylamino, alkenylamino, cycloalkylamino, alkylcarbonylamino, cycloalkylcarbonylamino,
Arylcarbonylamino, Heteroarylcarbonylamino, Formylamino, Arylcarbonylamino, heteroarylcarbonylamino, formylamino,
Haloalkylcarbonylamino, Alkoxycarbonylamino, Alkylaminocarbonylamino, (Alkyl-)aminocarbonylamino, Alkylsulfonylamino, Cycloalkylsulfonylamino, Arylsulfonylamino, Hetarylsulfonylamino, Sulfonylhaloalkylamino, Haloalkylcarbonylamino, alkoxycarbonylamino, alkylaminocarbonylamino, (alkyl) aminocarbonylamino, alkylsulfonylamino, cycloalkylsulfonylamino, arylsulfonylamino, hetarylsulfonylamino, sulfonylhaloalkylamino,
Aminoalkylsulfonyl, Aminohaloalkylsulfonyl, Alkylaminosulfonyl, Aminoalkylsulfonyl, aminohaloalkylsulfonyl, alkylaminosulfonyl,
Bisalkylaminosulfonyl, Cycloalkylaminosulfonyl, Haloalkylaminosulfonyl, Heteroarylaminosulfonyl, Arylaminosulfonyl, Arylalkylaminosulfonyl, Bisalkylaminosulfonyl, cycloalkylaminosulfonyl, haloalkylaminosulfonyl, heteroarylaminosulfonyl, arylaminosulfonyl, arylalkylaminosulfonyl,
Alkylsulfonyl, Cycloalkylsuifonyl, Arylsulfonyl, Hydroxycarbonyl, Alkoxycarbonyl, Cycloalkoxycarbonyl, Cycloalkylalkoxycarbonyl, Aryloxycarbonyl, Alkylsulfonyl, cycloalkylsulfonyl, arylsulfonyl, hydroxycarbonyl, alkoxycarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, aryloxycarbonyl,
Arylalkoxycarbonyl, Alkenyloxycarbonyl, Alkinyloxycarbonyl, Aminocarbonyl, Alkylaminocarbonyl, Bisalkylaminocarbonyl, Alkyl(Alkyl)aminocarbonyl, Arylalkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, aminocarbonyl, alkylaminocarbonyl, bisalkylaminocarbonyl, alkyl (alkyl) aminocarbonyl,
Alkyl(Alkoxy)aminocarbonyl, Alkenylaminocarbonyl, Cycloalkylaminocarbonyl, Arylaminocarbonyl, Arylalkylaminocarbonyl stehen, Alkyl (alkoxy) aminocarbonyl, alkenylaminocarbonyl, cycloalkylaminocarbonyl, arylaminocarbonyl, arylalkylaminocarbonyl,
A1, A2, A3 und A4 gleich oder verschieden sind und unabhängig voneinander für NA 1 , A 2 , A 3 and A 4 are the same or different and are independently N
(Stickstoff) oder die Gruppierungen C-H, C-CH3, C-F, C-Cl, C-Br, C-l, C-OCF3, C-OCH3, C-CF3, C-CO2H, C-CO2CH3 stehen, wobei jedoch in keinem Fall mehr als zwei N-Atome benachbart sind, (Nitrogen) or the groupings CH, C-CH 3, CF, C-Cl, C-Br, CI, C-OCF3, C-OCH3, C-CF3, C-CO2H, C-CO2CH3 are, however, in no more than two N-atoms are adjacent,
R11 und R12 unabhängig voneinander für Wasserstoff, Halogen, Alkyl, Aryl, Heteroaryl, Heterocyclyl, Cycloalkyl, Alkenyl, Alkinyl, Alkoxy, Alkoxyalkyl, Aryloxyalkyl,
Haloalkoxy, Haloalkyl, Haloalkoxyalkyl, Alkoxyhaloalkyl, Haloalkoxyhaloalkyl, Alkylthio, Haloalkylthio, Alkylthioalkyl, Hydroxycarbonyl, Alkoxycarbonyl, Cycloalkoxycarbonyl, Cycloalkylalkoxycarbonyl, Aryloxycarbonyl, R 11 and R 12 independently of one another represent hydrogen, halogen, alkyl, aryl, heteroaryl, heterocyclyl, cycloalkyl, alkenyl, alkynyl, alkoxy, alkoxyalkyl, aryloxyalkyl, Haloalkoxy, haloalkyl, haloalkoxyalkyl, alkoxyhaloalkyl, haloalkoxyhaloalkyl, alkylthio, haloalkylthio, alkylthioalkyl, hydroxycarbonyl, alkoxycarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, aryloxycarbonyl,
Arylalkoxycarbonyl, Alkenyloxycarbonyl, Alkinyloxycarbonyl, Aminocarbonyl, Alkylaminocarbonyl, Bisalkylaminocarbonyl, Alkyl(Alkyl)aminocarbonyl, Arylalkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, aminocarbonyl, alkylaminocarbonyl, bisalkylaminocarbonyl, alkyl (alkyl) aminocarbonyl,
Alkyl(Alkoxy)aminocarbonyl, Alkenylaminocarbonyl, Cycloalkylaminocarbonyl, Arylaminocarbonyl, Arylalkylaminocarbonyl, Cycloalkylthio, Heterocyclylthio, Alkylsulfinyl, Arylsulfinyl, Heteroarylsulfinyl, Cycloalkylsulfinyl, Alkyl (alkoxy) aminocarbonyl, alkenylaminocarbonyl, cycloalkylaminocarbonyl, arylaminocarbonyl, arylalkylaminocarbonyl, cycloalkylthio, heterocyclylthio, alkylsulfinyl, arylsulfinyl, heteroarylsulfinyl, cycloalkylsulfinyl,
Heterocyclylsulfinyl, Alkylsulfonyl, Arylsulfonyl, Heteroarylsulfonyl, Heterocyclylsulfinyl, alkylsulfonyl, arylsulfonyl, heteroarylsulfonyl,
Cycloalkylsulfonyl, Heterocyclyisulfonyl stehen, Cycloalkylsulfonyl, heterocyclyisulfonyl,
A5 für S (Schwefel), O (Sauerstoff) oder die Gruppierungen N-H, N-CH3, N-CH2CH3, N- CH(CH3)2, N-C02t-Bu, N-Aryl, N-Heteroaryl, N-Heterocyclyl steht, A 5 for S (sulfur), O (oxygen) or the groupings NH, N-CH 3 , N-CH 2 CH 3 , N-CH (CH 3 ) 2 , N-CO 2 t-Bu, N-aryl, N-heteroaryl , N-heterocyclyl,
R13, R14, R17 und R 8 unabhängig voneinander für Wasserstoff, Alkyl, Halogen, R 13 , R 14 , R 17 and R 8 independently of one another represent hydrogen, alkyl, halogen,
Cycloalkyl, Aryl, Heteroaryl, Heterocyclyl, Alkenyl, Alkinyl, Alkenylalkyl, Cycloalkyl, aryl, heteroaryl, heterocyclyl, alkenyl, alkynyl, alkenylalkyl,
Arylalkyl, Alkoxy, Alkoxyalkoxy, Alkoxyalkyl, Hydroxy, Haloalkyl, Haloalkylthio, Alkylthio, Arylthio, Cycloalkylthio, Heterocyclylthio, Alkylsulfinyl, Arylsulfinyl, Heteroarylsulfinyl, Cycloalkylsulfinyl, Heterocyclylsulfinyl, Alkylsulfonyl, Arylalkyl, alkoxy, alkoxyalkoxy, alkoxyalkyl, hydroxy, haloalkyl, haloalkylthio, alkylthio, arylthio, cycloalkylthio, heterocyclylthio, alkylsulfinyl, arylsulfinyl, heteroarylsulfinyl, cycloalkylsulfinyl, heterocyclylsulfinyl, alkylsulfonyl,
Arylsulfonyl, Heteroarylsulfonyl, Cycloalkylsulfonyl, Heterocyclyisulfonyl stehen oder Arylsulfonyl, heteroarylsulfonyl, cycloalkylsulfonyl, heterocyclyisulfonyl or
R13 und R17 mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls weiter substituierten 5 bis 7-gliedrigen Ring bilden. R 13 and R 17 with the atoms to which they are attached form a fully saturated or partially saturated, optionally further substituted 5 to 7-membered ring.
A6, A7 gleich oder verschieden sind und unabhängig voneinander für O (Sauerstoff), S (Schwefel), S=0, S(=0)2, N-H, N+-CH3(-0"), N-OCH3, N-CH3 oder die A 6 , A 7 are the same or different and are independently O (oxygen), S (sulfur), S = O, S (= O) 2 , NH, N + -CH 3 (-O " ), N -OCH 3 , N-CH 3 or the
Gruppierung CR15R16 stehen, wobei jedoch in keinem Fall zwei O- oder S- Atome benachbart sind, und wobei R15 und R16 in der Gruppierung CR15R16 jeweils gleiche oder verschiedene Bedeutungen gemäß der nachstehenden Definition haben und
R15 und R16 unabhängig voneinander für Wasserstoff, Halogen, Alkyl, Aryl, Heteroaryl, Heterocyclyl, Cycloalkyl, Alkenyl, Alkoxy, Alkoxyalkyl, Aryloxyalkyl, Haloalkoxy, Haloalkyl, Haloalkoxyalkyl, Alkoxyhaloalkyl, Haloalkoxyhaloalkyl, Alkylthio, Haloalkylthio, Alkylthioalkyl, Hydroxycarbonyl, Alkoxycarbonyl, Grouping CR 15 R 16 , but in no case are two O or S atoms adjacent, and wherein R 15 and R 16 in the group CR 15 R 16 each have the same or different meanings as defined below, and R 15 and R 16 independently of one another are hydrogen, halogen, alkyl, aryl, heteroaryl, heterocyclyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl, aryloxyalkyl, haloalkoxy, haloalkyl, haloalkoxyalkyl, alkoxyhaloalkyl, haloalkoxyhaloalkyl, alkylthio, haloalkylthio, alkylthioalkyl, hydroxycarbonyl, alkoxycarbonyl,
Cycloalkoxycarbonyl, Cycloalkylalkoxycarbonyl, Aryloxycarbonyl, Cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, aryloxycarbonyl,
Arylalkoxycarbonyl, Alkenyloxycarbonyl, Alkinyloxycarbonyl, Aminocarbonyl, Alkylaminocarbonyl, Bisalkylaminocarbonyl, Alkyl(Alkyl)aminocarbonyl, Alkyl(Alkoxy)aminocarbonyl, Alkenylaminocarbonyl, Cycloalkylaminocarbonyl, Arylaminocarbonyl, Arylalkylaminocarbonyl, Amino, Alkylamino, Arylalkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, aminocarbonyl, alkylaminocarbonyl, bisalkylaminocarbonyl, alkyl (alkyl) aminocarbonyl, alkyl (alkoxy) aminocarbonyl, alkenylaminocarbonyl, cycloalkylaminocarbonyl, arylaminocarbonyl, arylalkylaminocarbonyl, amino, alkylamino,
Cycloalkylamino, Bis-Alkylamino, Arylthio, Cycloalkylthio, Heterocyclylthio, Cycloalkylamino, bis-alkylamino, arylthio, cycloalkylthio, heterocyclylthio,
Alkylsulfinyl, Arylsulfinyl, Heteroarylsulfinyl, Cycloalkylsulfinyl, Alkylsulfinyl, arylsulfinyl, heteroarylsulfinyl, cycloalkylsulfinyl,
Heterocyclylsulfinyl, Alkylsulfonyl, Arylsulfonyl, Heteroaryisuifonyl, Heterocyclylsulfinyl, alkylsulfonyl, arylsulfonyl, heteroaryisuifonyl,
Cycloalkylsuifonyl, Heterocyclyisulfonyl stehen, R19, R20, R22 und R23 unabhängig voneinander für Wasserstoff, Alkyl, Halogen, Cycloalkylsuifonyl, Heterocyclyisulfonyl, R 19 , R 20 , R 22 and R 23 are each independently hydrogen, alkyl, halogen,
Cycloalkyl, Aryl, Heteroaryl, Heterocyclyl, Alkenyl, Alkinyl, Arylalkyl, Cycloalkyl, aryl, heteroaryl, heterocyclyl, alkenyl, alkynyl, arylalkyl,
Heterocyclylalkyl, Alkoxy, Alkoxyalkoxy, Alkoxyalkyl, Haloalkyl, Alkylthio, Arylthio, Cycloalkylthio, Heterocyclylthio, Alkylsulfinyl, Arylsulfinyl, Heterocyclylalkyl, alkoxy, alkoxyalkoxy, alkoxyalkyl, haloalkyl, alkylthio, arylthio, cycloalkylthio, heterocyclylthio, alkylsulfinyl, arylsulfinyl,
Heteroarylsulfinyl, Cycloalkylsulfinyl, Heterocyclylsulfinyl, Alkylsulfonyl, Heteroarylsulfinyl, cycloalkylsulfinyl, heterocyclylsulfinyl, alkylsulfonyl,
Arylsulfonyl, Heteroaryisuifonyl, Cycloalkylsuifonyl, Heterocyclyisulfonyl stehen, Arylsulfonyl, heteroaryisuifonyl, cycloalkylsulfonyl, heterocyclyisulfonyl,
A8 für O (Sauerstoff), S (Schwefel), S=0, S(=0)2, N-H, N+-CH3(-0 ), N-CH3, N-OCH3 oder die Gruppierung CHR21 steht und wobei R21 in der Gruppierung CHR21 die Bedeutung gemäß der nachstehenden Definition hat, A 8 represents O (oxygen), S (sulfur), S = O, S (= O) 2 , NH, N + -CH 3 (-O), N-CH 3 , N-OCH 3 or the group CHR 21 and wherein R 21 in the grouping CHR 21 has the meaning as defined below,
R21 für Wasserstoff, Halogen, Alkyl, Aryl, Heteroaryl, Heterocyclyl, Cycloalkyl, Alkenyl, Alkinyl, Heterocyclylalkyl, Alkoxy, Alkoxyalkyl, Aryloxyalkyl, Haloalkoxy, Haloalkyl, Alkoxyhaloalkyl, Haloalkoxyhaloalkyl, Alkylthio, Haloalkylthio, Alkylthioalkyl, Hydroxycarbonyl, Alkoxycarbonyl, Cycloalkoxycarbonyl, R 21 is hydrogen, halogen, alkyl, aryl, heteroaryl, heterocyclyl, cycloalkyl, alkenyl, alkynyl, heterocyclylalkyl, alkoxy, alkoxyalkyl, aryloxyalkyl, haloalkoxy, haloalkyl, alkoxyhaloalkyl, haloalkoxyhaloalkyl, alkylthio, haloalkylthio, alkylthioalkyl, hydroxycarbonyl, alkoxycarbonyl, cycloalkoxycarbonyl,
Arylalkoxycarbonyl, Alkenyloxycarbonyl, Alkinyloxycarbonyl, Aminocarbonyl, Arylalkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, aminocarbonyl,
Alkylaminocarbonyl, Bisalkylaminocarbonyl, Alkyl(Alkyl)aminocarbonyl, Alkyl(Alkoxy)aminocarbonyl, Alkenylaminocarbonyl, Cycloalkylaminocarbonyl, Arylaminocarbonyl, Arylalkylaminocarbonyl, Amino, Alkylamino, Alkylaminocarbonyl, bisalkylaminocarbonyl, alkyl (alkyl) aminocarbonyl, alkyl (alkoxy) aminocarbonyl, alkenylaminocarbonyl, cycloalkylaminocarbonyl, arylaminocarbonyl, arylalkylaminocarbonyl, amino, alkylamino,
Cycloalkylamino, Bis-Alkylamino, Arylthio, Cycloalkylthio, Heterocyclylthio,
Alkylsulfinyl, Arylsulfinyl, Heteroarylsulfinyl, Cycloalkylsulfinyl, Heterocyclylsulfinyl, Alkylsulfonyl, Arylsulfonyl, Heteroarylsulfonyl, Cycloalkylamino, bis-alkylamino, arylthio, cycloalkylthio, heterocyclylthio, Alkylsulfinyl, arylsulfinyl, heteroarylsulfinyl, cycloalkylsulfinyl, heterocyclylsulfinyl, alkylsulfonyl, arylsulfonyl, heteroarylsulfonyl,
Cycloalkylsulfonyl, Heterocyclylsulfonyl steht, Cycloalkylsulfonyl, heterocyclylsulfonyl,
R24, R25, R26, R28, R29 und R30 unabhängig voneinander für Wasserstoff, Alkyl, R 24 , R 25 , R 26 , R 28 , R 29 and R 30 are each independently hydrogen, alkyl,
Halogen, Cycloalkyl, Aryl, Heteroaryl, Heterocyclyl, Alkenyl, Alkoxy, Halogen, cycloalkyl, aryl, heteroaryl, heterocyclyl, alkenyl, alkoxy,
Alkoxyalkoxy, Alkoxyalkyl, Haloalkyl, Alkylthio, Haloalkylthio, Arylthio, Alkoxyalkoxy, alkoxyalkyl, haloalkyl, alkylthio, haloalkylthio, arylthio,
Cycloalkylthio, Heterocyclylthio, Alkylsulfinyl, Arylsulfinyl, Heteroarylsulfinyl, Cycloalkylsulfinyl, Heterocyclylsulfinyl, Alkylsulfonyl, Arylsulfonyl, Cycloalkylthio, heterocyclylthio, alkylsulfinyl, arylsulfinyl, heteroarylsulfinyl, cycloalkylsulfinyl, heterocyclylsulfinyl, alkylsulfonyl, arylsulfonyl,
Heteroarylsulfonyl, Cycloalkylsulfonyl, Heterocyclylsulfonyl stehen, Heteroarylsulfonyl, cycloalkylsulfonyl, heterocyclylsulfonyl,
A9 für O (Sauerstoff), S (Schwefel), S=0, S(=0)2, N-H, N+-CH3(-0-), N-CH3, N-OCH3 oder die Gruppierung CHR27 steht und wobei R27 in der Gruppierung CHR27 die Bedeutung gemäß der nachstehenden Definition hat und A 9 is O (oxygen), S (sulfur), S = O, S (= O) 2 , NH, N + -CH 3 (-O-), N-CH 3 , N-OCH 3 or the moiety CHR 27 and wherein R 27 in the grouping CHR 27 has the meaning as defined below, and
R27 für Wasserstoff, Halogen, Alkyl, Aryl, Heteroaryl, Heterocyclyl, Cycloalkyl, Alkenyl, Alkoxy, Alkoxyalkyl, Aryloxy alkyl, Haloalkoxy, Haloalkyl, Alkylthio, Haloalkylthio, Hydroxycarbonyl, Alkoxycarbonyl, Cycloalkoxycarbonyl, Arylalkoxycarbonyl, Alkenyloxycarbonyl, Alkinyloxycarbonyl, Aminocarbonyl, Alkylaminocarbonyl, Bisalkylaminocarbonyl, Alkyl(Alkyl)aminocarbonyl, Alkyl(Alkoxy)aminocarbonyl, Alkenylaminocarbonyl, Cycloalkylaminocarbonyl, Arylaminocarbonyl, R 27 is hydrogen, halogen, alkyl, aryl, heteroaryl, heterocyclyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl, aryloxyalkyl, haloalkoxy, haloalkyl, alkylthio, haloalkylthio, hydroxycarbonyl, alkoxycarbonyl, cycloalkoxycarbonyl, arylalkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, aminocarbonyl, alkylaminocarbonyl, Bisalkylaminocarbonyl, alkyl (alkyl) aminocarbonyl, alkyl (alkoxy) aminocarbonyl, alkenylaminocarbonyl, cycloalkylaminocarbonyl, arylaminocarbonyl,
Arylalkylaminocarbonyl, Amino, Alkylamino, Cycloalkylamino, Bis-Alkylamino, Arylthio, Cycloalkylthio, Heterocyclylthio, Alkylsulfinyl, Arylsulfinyl, Arylalkylaminocarbonyl, amino, alkylamino, cycloalkylamino, bis-alkylamino, arylthio, cycloalkylthio, heterocyclylthio, alkylsulfinyl, arylsulfinyl,
Heteroarylsulfinyl, Cycloalkylsulfinyl, Heterocyclylsulfinyl, Alkylsulfonyl, Heteroarylsulfinyl, cycloalkylsulfinyl, heterocyclylsulfinyl, alkylsulfonyl,
Arylsulfonyl, Heteroarylsulfonyl, Cycloalkylsulfonyl, Heterocyclylsulfonyl steht. Arylsulfonyl, heteroarylsulfonyl, cycloalkylsulfonyl, heterocyclylsulfonyl.
Die Verbindungen der allgemeinen Formel (I) können durch Anlagerung einer geeigneten anorganischen oder organischen Säure, wie beispielsweise Mineralsäuren, wie beispielsweise HCl, HBr, H2SO4, H3PO4 oder HNO3, oder organische Säuren, z. B. Carbonsäuren, wie Ameisensäure, Essigsäure, Propionsäure, Oxalsäure, Milchsäure oder Salicylsäure oder Sulfonsäuren, wie zum Beispiel p-Toluolsulfonsäure, an eine basische Gruppe, wie z.B. Amino, Alkylamino, Dialkylamino, Piperidino, Morpholino oder Pyridino, Salze bilden. Diese Salze enthalten dann die konjugierte Base der Säure als Anion. Geeignete Substituenten, die in deprotonierter Form, wie z.B.
Sulfonsäuren oder Carbonsäuren, vorliegen, können innere Salze mit ihrerseits protonierbaren Gruppen, wie Aminogruppen bilden. The compounds of general formula (I) may be prepared by addition of a suitable inorganic or organic acid such as, for example, mineral acids such as HCl, HBr, H 2 SO 4, H 3 PO 4 or HNO 3, or organic acids, e.g. For example, carboxylic acids such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid or sulfonic acids such as p-toluenesulfonic acid to form a basic group such as amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino, salts. These salts then contain the conjugate base of the acid as an anion. Suitable substituents which are in deprotonated form, such as Sulfonic acids or carboxylic acids, may form internal salts with their turn protonatable groups, such as amino groups.
Im Folgenden werden die erfindungsgemäß verwendeten Verbindungen der Formel (I) und ihre Salze "Verbindungen der allgemeinen Formel (I)" bezeichnet. The compounds of the formula (I) used according to the invention and their salts are referred to below as "compounds of the general formula (I)".
Bevorzugt ist die erfindungsgemäße Verwendung von Verbindungen der allgemeinen Formel (I), worin [X-Y] für die Gruppierungen Preference is given to the use according to the invention of compounds of the general formula (I) in which [X-Y] is the grouping
[X-Y]1 und ίχ-γ]3 steht, [XY] 1 and ί χ - γ ] 3 ,
Q für die Gruppierungen Q-1 bis Q-6 Q for the groupings Q-1 to Q-6
Q-1 Q-2 Q-3 Q-1 Q-2 Q-3
Q-4 Q-5 und Q-6 steht, wobei R7, R8, R9, R1Ü, R11, R12, R13, R14, R17, R18, R19, R20, R22, R23, R24, R25, R26, R28, R29 und R30 und A1 bis A9 jeweils die Bedeutung gemäß der nachstehenden Definitionen haben und wobei der Pfeil für eine Bindung zur jeweiligen Gruppierung C-R6 in der allgemeinen Formel (I) steht,
R1 für (Ci-Cs)-Alkyl, (C3-C8)-Cycloalkyl, (C4-C8)-Cycloalkenyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (C2-C8)-Alkenyl-(CrC8)-alkyl, (C2-C8)-Alkinyl-(Ci-C8)-alkyl, (Ci-C8)-Alkoxy-(CrC8)-alkyl, Hydroxy-(Ci-C8)-alkyl, (Ci-C8)-Haloalkyl, (C2-C8)- Haloalkenyl, (C2-C8)-Haloalkinyl, (Ci-C8)-Haloalkoxy-(CrC8)-alkyl, (Ci-C8)- Alkoxy-(CrC8)-haloalkyl, (Ci-C8)-Haloalkoxy-(Ci-C8)-haloalkyl, (d-Ce)- Alkylthio-(Ci-C8)-alkyL (Ci-C8)-Haloalkylthio-(Ci-C8)-alkyl, Aryl, Heteroaryl, Heterocyclyl steht, Q-4 Q-5 and Q-6 wherein R 7 , R 8 , R 9 , R 1Ü , R 11 , R 12 , R 13 , R 14 , R 17 , R 18 , R 19 , R 20 , R 22 , R 23 , R 24 , R 25 , R 26 , R 28 , R 29 and R 30 and A 1 to A 9 are each as defined below, and wherein the arrow indicates a bond to the respective grouping CR 6 in the general formula (I), R 1 is (Ci-Cs) alkyl, (C 3 -C 8) cycloalkyl, (C 4 -C 8) cycloalkenyl, (C2-C8) alkenyl, (C 2 -C 8) alkynyl, (C 2 -C 8) alkenyl (-C 8) alkyl, (C 2 -C 8) alkynyl (Ci-C 8) alkyl, (Ci-C 8) alkoxy (CrC 8) - alkyl, hydroxy (Ci-C 8) alkyl, (Ci-C 8) haloalkyl, (C 2 -C 8) - haloalkenyl, (C 2 -C 8) haloalkynyl, (Ci-C8) -haloalkoxy - (CrC 8) alkyl, (Ci-C8) - alkoxy (-C 8) -haloalkyl, (Ci-C8) haloalkoxy (Ci-C 8) haloalkyl, (d-Ce) - alkylthio (C 1 -C 8 ) -alkyL (C 1 -C 8 ) -haloalkylthio (C 1 -C 8 ) -alkyl, aryl, heteroaryl, heterocyclyl,
R2, R3 und R4 unabhängig voneinander für Wasserstoff, Halogen, (Ci-Cs)-Alkyl, R 2 , R 3 and R 4 independently of one another represent hydrogen, halogen, (C 1 -C 5) -alkyl,
(C3-C8)-Cycloalkyl, (C4-C8)-Cycloalkenyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (C -C8)-Alkenyl-(CrC8)-alkyl, (C2-C8)-Alkinyl-(Ci-C8)-alkyl, (Ci-C8)-Alkoxy- (Ci-Cs)-alkyl, Hydroxy-(Ci-C8)-alkyl, (Ci-C8)-Haloalkyl, (C2-C8)-Haloalkenyl, (C2-C8)-Haloalkinyl, (Ci-C8)-Haloalkoxy-(d-C8)-alkyl, (Ci-C8)-Alkoxy-(d-C8)- haloalkyl, (Ci-C8)-Haloalkoxy-(CrC8)-haloalkyl, (CrC8)-Alkylthio-(Ci-C8)-alkyl, (Ci-C8)-Haloalkylthio-(Ci-C8)-alkyl, Aryl, Heteroaryl, Heterocyclyl stehen, (C 3 -C 8 ) -cycloalkyl, (C 4 -C 8 ) -cycloalkenyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl, (C 2 -C 8 ) -alkenyl- ( -C 8) alkyl, (C 2 -C 8) alkynyl (Ci-C 8) alkyl, (Ci-C 8) alkoxy (Ci-Cs) alkyl, hydroxy (Ci-C 8) alkyl, (Ci-C 8) haloalkyl, (C 2 -C 8) -haloalkenyl, (C 2 -C 8) haloalkynyl, (Ci-C8) haloalkoxy (dC 8) alkyl, (C -C 8 ) alkoxy (dC 8 ) haloalkyl, (Ci-C 8 ) haloalkoxy (CrC 8 ) haloalkyl, (CrC 8 ) alkylthio (Ci-C 8 ) alkyl, (Ci-C 8 ) -haloalkylthio (C 1 -C 8 ) -alkyl, aryl, heteroaryl, heterocyclyl,
R5 für Hydroxy, (CrCs)-Alkoxy, Aryioxy, (C3-C8)-Cycloalkyloxy, (C2-C8)-Alkenyloxy, (C2-C8)-Alkenyl-(Ci-C8)-alkyloxy, (Ci-C8)-Alkoxy-(Ci-C8)-alkyloxy, (Ci-C8)- Alkylcarbonyloxy, Arylcarbonyloxy, Heteroarylcarbonyloxy, (C3-C8)- Cycloalkylcarbonyloxy, (Ci-C8)-Alkoxycarbonyloxy, (C2-C8)- Alkenyloxycarbonyloxy, Aryloxy-(Ci-C8)-alkyloxy, Aryl-(Ci-C8)-alkyloxy, (d-C8)- Alkoxy-(Ci-C8)-alkoxy-(Ci-C8)-alkyloxy, (Ci-C8)-Alkylthio-(Ci-C8)-alkyloxy, Tris[(Ci-C8)-alkyl]silyloxy, (CrC8)-Alkyl-Bis[(Ci-C8)-alkyl]silyloxy, (Ci-C8)-Alkyl- bis(Aryl)silyloxy, Aryl-bis[(Ci-C8)— alkyl]silyloxy, Cycloalkyl-bis[(Ci-C8)- alkyl]silyloxy, Halo-bis[(Ci-C8)-alkyl]silyloxy, Tris[(Ci-C8)-alkyl]silyl-(CrC8)- alkoxy-(d-C8)-alkyloxy, steht, R 5 is hydroxy, (CRCs) alkoxy, Aryioxy, (C3-C8) cycloalkyloxy, (C 2 -C 8) alkenyloxy, (C 2 -C 8) alkenyl (Ci-C8) alkyloxy , (Ci-C 8) alkoxy (Ci-C8) alkyloxy, (Ci-C 8) - alkylcarbonyloxy, arylcarbonyloxy, heteroarylcarbonyloxy, (C3-C8) - cycloalkylcarbonyloxy, (Ci-C 8) alkoxycarbonyloxy, (C 2 -C 8) - Alkenyloxycarbonyloxy, aryloxy (Ci-C8) alkyloxy, aryl (Ci-C8) alkyloxy, (dC 8) - alkoxy (Ci-C 8) alkoxy (C -C 8) -alkyloxy, (Ci-C8) alkylthio (Ci-C8) alkyloxy, tris [(Ci-C 8) alkyl] silyloxy (-C 8) -alkyl-bis [(Ci- C 8) alkyl] silyloxy, (Ci-C 8) alkyl silyloxy bis (aryl), aryl-bis [(Ci-C 8) - alkyl] silyloxy, cycloalkyl-bis [(Ci-C 8) - alkyl ] silyloxy, halo-bis [(C 1 -C 8 ) -alkyl] silyloxy, tris [(C 1 -C 8 ) -alkyl] silyl (C 1 -C 8 ) -alkoxy (C 1 -C 8 ) -alkyloxy,
R6 für Nitro, Amino, Hydroxy, Hydrothio, Thiocyanato, Isothiocyanato, Halogen,R 6 for nitro, amino, hydroxy, hydrothio, thiocyanato, isothiocyanato, halogen,
(Ci-C8)-Alkyl, (C3-C8)-Cycloalkyl, (C2-C8)-Alkenyl, (C4-C8)-Cycloalkenyl, (C2-C8)- Alkinyl, Aryl-(C2-C8)-alkinyl, Tris[(CrC8)-alkyl]silyl-(C2-C8)-alkinyl, Aryl, Aryl- (CrCs)-alkyl, Aryl-(Ci-C8)-alkoxy, Heteroaryl, (d-C8)-Haloalkyl, (C3-C8)- Halocycloalkyl, (C2-C8)-Haloalkenyl, (Ci-C8)-Alkoxy, (d-C8)-Haloalkoxy, Aryioxy, Heteroaryloxy, (C3-C8)-Cycloalkyloxy, (C3-C8)-Cycloalkyl-(Ci-C8)- alkoxy, (C2-C8)- (C2-C8)-Alkenyloxy, (C2-C8)-Alkinyl-(C2-C8)-alkyloxy, Hydroxy-
(Ci-Cs)-alkyl, (Ci-C8)-Alkoxy-(Ci-Ce)-alkyl, Aryloxy-(Ci-C8)-alkyl, Heteroaryloxy- (CrC8)-alkyl, (Ci-Ce)-Alkylthio, (d-C8)-Haloalkylthio, (d-C8)-Alkoxycarbonyl- (d-C8)-alkylthio, Arylthio, (C3-C8)-Cycloalkylthio, Heteroarylthio, (d-C8)- Alkylthio-(Ci-C8)-alkyl, (Ci-C8)-Alkylamino, Bis[(Ci-C8)-alkyl]amino, (C2-C8)- Alkenylamino, (C3-C8)-Cycloalkylamino, (CrC8)-Alkylcarbonylamino, (Ca-Ca)- Cycloalkylcarbonylamino, Arylcarbonylamino, Heteroarylcarbonylamino, Formylamino, (d-CeJ-Haloalkylcarbonylamino, (CrCeJ-Alkoxycarbonylamino, (Ci-C8)-Alkylaminocarbonylamino, (Ci-C8)-Alkyl[(Ci-C8)- Alkyljaminocarbonylamino, (Ci-C8)-Alkylsulfonylamino, (C3-C8)- Cycloalkylsulfonylamino, Arylsulfonylamino, Hetarylsulfonylamino, Sulfonyl- (Ci-C8)-haloalkylamino, Amino-(CrC8)-alkylsulfonyl, Amino-(CrC8)- haloaikylsulfonyl, (Ci-C8)-Alkylaminosulfonyl, Bis[(Ci-C8)-alkyl]aminosulfonyl, (C3-C8)-Cycloalkylaminosulfonyl, (Ci-C8)-Haloalkylaminosulfonyl, Aminosulfonyl, Heteroarylaminosulfonyl, Arylaminosulfonyl, Aryl-(Ci-C8)-alkylaminosulfonyl, (Ci-Cs)-Alkylsulfonyl, (C3-C8)-Cycloalkylsu!fonyl, Arylsulfonyl, (Ci-Ce)- Alkylsulfinyl, (C3-C8)-Cycloalkylsulfinyl, Arylsulfinyl, N,S-Bis[(Ci-Ce)- alkyljsulfonimidoyl, S-(Ci-C8)-Alkylsulfonimidoyl, (d-Cs)- Alkylsulfonylaminocarbonyl, (Ca-CsJ-Cycloalkylsulfonylaminocarbonyl, Aryl- (Ci-C8)-alkylcarbonylamino, (C3-C8)-Cycloalkyl-(Ci-C8)-alkylcarbonylamino! Heteroarylcarbonylamino, (Ci-C8)-Alkoxy-(Ci-C8)-alkylcarbonylamino, Hydroxy- (Ci-Cs)-alkylcarbonylamino, (Ci-C8)-Alkoxycarbonylamino-(Ci-C8)- alkylcarbonylamino, Cyano, Cyano-(Ci-C8)-alkyl, Hydroxycarbonyl, (d-Cs)- Alkoxycarbonyl, (C3-C8)-Cycloalkoxycarbonyl, (C3-C8)-Cycloalkyl-(Ci-C8)- alkoxycarbonyl, Aryloxycarbonyl, Aryl-(Ci-C8)-alkoxycarbonyl, (C2-C-8)- Alkenyloxycarbonyl, (C2-C8)-Alkinyloxycarbonyl, (Ci-Cs)-Haloalkyloxycarbonyl, (Ci-C8)-Alkoxy-(Ci-C8)-alkoxycarbonyl, (C2-C8)-Alkenyloxy-(Ci-C8)- alkoxycarbonyl, (Ci-C8)-Alkylamino-(Ci-Cs)-alkoxycarbonyl, Tris[(Ci-Cs)- alkyl]silyloxy-(Ci-C8)-alkoxycarbonyl, Bis[(Ci-C8)-Alkyl]amino-(Ci-C8)- alkoxycarbonyl, (Ci-C8)-Alkyl[(Ci-C8)-alkyl]amino-(Ci-C8)-alkoxycarbonyl, Cyano-(Ci-C8)-alkoxycarbonyl, Heterocyclyl-N-(Ci-C8)-alkoxycarbonyl, (C 1 -C 8 ) -alkyl, (C 3 -C 8 ) -cycloalkyl, (C 2 -C 8 ) -alkenyl, (C 4 -C 8 ) -cycloalkenyl, (C 2 -C 8 ) -alkynyl, aryl - (C 2 -C 8 ) -alkynyl, tris [(C 1 -C 8 ) -alkyl] silyl- (C 2 -C 8 ) -alkynyl, aryl, aryl- (C 1 -C 5 ) -alkyl, aryl- (C 1 -C 8 ) alkoxy, heteroaryl, (dC 8) -haloalkyl, (C 3 -C 8) - halocycloalkyl, (C 2 -C 8) -haloalkenyl, (Ci-C 8) alkoxy, (dC 8) -haloalkoxy, Aryioxy, heteroaryloxy, (C3-C8) cycloalkyloxy, (C3-C8) -cycloalkyl- (Ci-C8) - alkoxy, (C 2 -C 8) - (C 2 -C 8) alkenyloxy, (C 2 -C 8 ) alkynyl (C 2 -C 8 ) alkyloxy, hydroxy (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkoxy- (C 1 -C 6) -alkyl, aryloxy- (C 1 -C 8 ) -alkyl, heteroaryloxy- (C 1 -C 8 ) -alkyl, (C 1 -C 4) - alkylthio, (dC 8) haloalkylthio, (dC 8) alkoxycarbonyl (dC 8) alkylthio, arylthio, (C 3 -C 8) cycloalkylthio, heteroarylthio, (dC 8) - alkylthio (Ci-C 8) alkyl, (Ci-C 8) alkylamino, bis [(Ci-C 8) alkyl] amino, (C 2 -C 8) - alkenylamino, (C3-C8) cycloalkylamino, (CrC 8) alkylcarbonylamino , (Ca-Ca) - cycloalkylcarbonylamino, arylcarbonylamino, heteroarylcarbonylamino, formylamino, (d-CeJ-haloalkylcarbonylamino, (CrCeJ-alkoxycarbonylamino, (Ci-C8) -alkylaminocarbonylamino, (Ci-C8) -alkyl [(Ci-C8) - alkyljaminocarbonylamino , (C 1 -C 8) -alkylsulfonylamino, (C 3 -C 8) -cycloalkylsulfonylamino, arylsulfonylamino, hetarylsulfonylamino, sulfonyl- (C 1 -C 8) -haloalkylamino, amino- (C 1 -C 8) -alkylsulfonyl, amino- (C 1 -C 8) -haloaikylsulfonyl, C 8 ) -alkylaminosulfonyl, bis [(C 1 -C 8 ) -alkyl] aminosulfonyl, (C 3 -C 8 ) -cycloalkylaminosulfonyl, (C 1 -C 8 ) -haloalkylaminosulfonyl, aminosulfonyl, heteroarylamino sulfonyl, arylaminosulfonyl, aryl (Ci-C8) -alkylaminosulfonyl, (Ci-Cs) alkylsulfonyl, (C 3 -C 8) -Cycloalkylsu fonyl, arylsulfonyl, (Ci-Ce) - alkylsulfinyl, (C 3 -C 8 ) -cycloalkylsulfinyl, arylsulfinyl, N, S-bis [(Ci-Ce) - alkylsulfonimidoyl, S- (Ci-C8) -alkylsulfonimidoyl, (d-Cs) - alkylsulfonylaminocarbonyl, (Ca-CsJ-Cycloalkylsulfonylaminocarbonyl, aryl- (Ci C8) alkylcarbonylamino, (C3-C8) -cycloalkyl- (Ci-C8) alkylcarbonylamino! Heteroarylcarbonylamino, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkylcarbonylamino, hydroxy- (C 1 -C 8 ) -alkylcarbonylamino, (C 1 -C 8 ) -alkoxycarbonylamino- (C 1 -C 8 ) -alkylcarbonylamino, cyano, cyano - (Ci-C 8) alkyl, hydroxycarbonyl, (d-Cs) - alkoxycarbonyl, (C 3 -C 8) -cycloalkoxycarbonyl, (C 3 -C 8) cycloalkyl (Ci-C8) - alkoxycarbonyl, aryloxycarbonyl , Aryl- (C 1 -C 8 ) -alkoxycarbonyl, (C 2 -C 8 ) -alkenyloxycarbonyl, (C 2 -C 8 ) -alkynyloxycarbonyl, (C 1 -C 8 ) -haloalkyloxycarbonyl, (C 1 -C 8 ) -alkoxy- (ci) C 8 ) -alkoxycarbonyl, (C 2 -C 8 ) -alkenyloxy- (C 1 -C 8 ) -alkoxycarbonyl, (C 1 -C 8 ) -alkylamino- (C 1 -C 8 ) -alkoxycarbonyl, tris [(C 1 -C 8 ) -alkyl] silyloxy- (C 1 -C 8 ) -alkoxycarbonyl, bis [(C 1 -C 8 ) -alkyl] amino- (C 1 -C 8 ) -alkoxycarbonyl, (C 1 -C 8 ) -alkyl [(C 1 -C 8 ) -alkyl] amino- (C 1 -C 8 ) -alkoxycarbonyl, cyano- (C 1 -C 8 ) -alkoxycarbonyl, heterocyclyl-N- (C 1 -C 8 ) -alkoxycarbonyl,
HeteroaryioxycarbonyL Heteroaryl-(d-C8)-alkoxycarbonyl, Heterocyclyl-(Ci-Cs)- alkoxycarbonyl, Heterocyclyloxycarbonyl, (C2-C8)-Alkenyl-(Ci-C8)- alkoxycarbonyl, (C2-C8)-Alkinyl-(Ci-C8)-alkoxycarbonyl, Aryl-(C2-Cs)- alkinyloxycarbonyl, Aryl-(C2-C8)-alkenyloxycarbonyl, Aminocarbonyl, (d-Cs)-
Alkylaminocarbonyl, Bis[(Ci-C8)-alkyl]aminocarbonyl, (Ci-C8)-Alkyl[(Ci-C8)- Alkyl]aminocarbonyl, (Ci-C8)-Alkyl[(Ci-C8)-Alkoxy]aminocarbonyl, (C2-C-8)- Alkenylaminocarbonyl, (C3-C8)-Cycloalkylaminocarbonyl, Arylaminocarbonyl, Aryl-(Ci-C8)-alkylaminocarbonyl, Heteroaryl-(Ci-C8)-alkylaminocarbonyl, Cyano- (CrC8)-alkylaminocarbonyl, (CrCs)-Haloalkylaminocarbonyl, (C2-C8)-Alkinyl- (Ci-C8)-alkylaminocarbonyl, (Ci-C8)-Alkoxycarbonylaminocarbonyl, Aryl-(Ci-C8)- alkoxycarbonylaminocarbonyl, Hydroxycarbonyl-(Ci-C8)-alkyl, (Ci-C8)- Alkoxycarbonyl-(Ci-C8)-alkyl, (C3-C8)-Cycloalkoxycarbonyl-(CrC8)-alkyl, (C3-C8)-Cycloalkyl-(Ci-C8)-alkoxycarbony!-(Ci-C8)-alkyl, (C2-C8)- Alkenyloxycarbonyl-(Ci-C8)-alkyl, Aryl-(Ci-C8)-alkoxycarbonyl-(Ci-C8)-alkyl, (Ci-C8)-Alkylaminocarbonyl-(CrC8)-alkyl, Aminocarbonyl-(CrC8)-alkyl, HeteroaryioxycarbonyL heteroaryl (d-C8) -alkoxycarbonyl, heterocyclyl (Ci-Cs) - alkoxycarbonyl, heterocyclyloxycarbonyl, (C2-C8) alkenyl (Ci-C8) - alkoxycarbonyl, (C 2 -C 8) alkynyl (Ci-C8) -alkoxycarbonyl, aryl- (C2-Cs) -alkinyloxycarbonyl, aryl- (C2-C8) -alkenyloxycarbonyl, aminocarbonyl, (d-Cs) - Alkylaminocarbonyl, bis [(C 1 -C 8 ) -alkyl] aminocarbonyl, (C 1 -C 8 ) -alkyl [(C 1 -C 8 ) -alkyl] aminocarbonyl, (C 1 -C 8 ) -alkyl [(C 1 -C 8 ) -alkoxy ] aminocarbonyl, (C2-C8) - alkenylaminocarbonyl, (C3-C8) cycloalkylaminocarbonyl, arylaminocarbonyl, aryl (Ci-C 8) alkylaminocarbonyl, heteroaryl (Ci-C8) alkylaminocarbonyl, cyano (CRC8) alkylaminocarbonyl, (C 1 -C 5) -haloalkylaminocarbonyl, (C 2 -C 8 ) -alkynyl- (C 1 -C 8 ) -alkylaminocarbonyl, (C 1 -C 8 ) -alkoxycarbonylaminocarbonyl, aryl- (C 1 -C 8 ) -alkoxycarbonylaminocarbonyl, hydroxycarbonyl- Ci-C 8) alkyl, (Ci-C8) - alkoxycarbonyl, (Ci-C 8) alkyl, (C3-C8) -Cycloalkoxycarbonyl- (CRC8) alkyl, (C 3 -C 8) -cycloalkyl- ( Ci-C8) -alkoxycarbony - (Ci-C 8) alkyl, (C 2 -C 8) - alkenyloxycarbonyl (Ci-C 8) alkyl, aryl (Ci-C8) alkoxycarbonyl (Ci- C 8 ) -alkyl, (C 1 -C 8 ) -alkylaminocarbonyl- (C 1 -C 8 ) -alkyl, aminocarbonyl- (C 1 -C 8 ) -alkyl,
Bis[(Ci-C8)-alkyl]aminocarbonyl-(Ci-C8)-alkyl, (C: C8)-Cycloalkylaminocarbonyl- (CrC8)-alkyl, Aryl-(Ci-C8)-alkylaminocarbonyl-(Ci-C8)-alkyl, Heteroaryl-(Ci-C8)- alkylaminocarbonyl-(CrC8)-alkyl, Cyano-(Ci-C8)-alkylaminocarbonyl-(CrC8)- alkyl, (Ci-C8)-Haloaikylaminocarbonyl-(Ci-C8)-alkyl, (C2-C8)-Alkinyl-(d-C8)- alkylaminocarbonyl-(Ci-C8)-alkyl, (C3-C8)-Cycloalkyl-(Ci-C8)- alkylaminocarbonyl-(CrC8)-alkyl, (Ci-C8)-Alkoxycarbonylaminocarbonyl- (Ci-Ce)-alkyl, Aryl-(Ci-C8)-alkoxycarbonylaminocarbonyl-(Ci-C8)-alkyl, (Ci-C8)- Alkoxycarbonyl-(Ci-C8)-alkylaminocarbonyl, Hydroxycarbonyl-(Ci-C8)- alkylaminocarbonyl, Aryl-(Ci-C8)-alkoxycarbonyl-(Ci-Cs)-alkylaminocarbonyl, (CrC8)-Alkoxycarbonyl-heterocyclyl-N-carbonyl, (Ci-C8)-Alkoxycarbonyl-(Ci- C8)-alkyl-heterocyclylidenaminocarbonyl, (Ci-C8)- Alkoxycarbonylheterocyclyliden-(CrC8)-alkylaminocarbonyl (Ci-C8)- Alkoxycarbonyl-(Ci-C8)-Alkyl((Ci-C8)-alkyl)aminocarbonyl, (Ci-C8)- Alkoxycarbonyl-(C3-C8)-cycloalkylidenaminocarbonyl, Heterocyclyl-N-carbonyl, (Ci-C8)-Alkoxy-(Ci-C8)-alkylaminocarbonyl, Aminocarbonyl-(Ci-C8)- alkylaminocarbonyl, (Ci-C8)-Alkylaminocarbonyl-(Ci-C8)-alkylaminocarbonyl, (C3-Cs)-Cycloalkylaminocarbonyl-(Ci-C8)-alkylaminocarbonyl, (Ca-Cs)- Cycloalkyl-(Ci-C8)-alkylaminocarbony!, (C3-C8)-Cycloalkyl-(Ci-C8)- alkylaminocarbonyl-(Ci-C8)-alkyl, (C3-C8)-Cycloafkyl-(Ci-C8)- alkylaminocarbonyl-(Ci-C8)-alkylaminocarbonyl, (C2-C8)-Alkenyl-(Ci-C8)- alkylaminocarbonyl, (C2-C8)-Alkenylaminocarbonyl-(Ci-C8)-alkyl, (C2-Cs)- Alkenyl-(Ci-C8)-alkylaminocarbonyl-(Ci-C8)-alkyl, (Ci-Ce)-Alkylcarbonyl, (C3-C8)- Cycloalkylcarbonyl, Arylcarbonyl, Formyl, Hydroxyiminomethyl,
Aminoiminomethyl, (Ci-C8)-Alkoxyiminomethyl, (Ci-C8)-Alkylaminoiminomethyl, Bis[(Ci-C8)-alkyl]aminoiminomethyl, (Ca-CeJ-Cycloalkoxyiminomethyl, (Ca-Ce)- Cycloaikyl-(Ci-C8)-alkoximinomethyl, Aryloximinomethyl, Aryl-(Ci-Cs)- alkoxyiminomethyl, Aryl-(Ci-C8)-alkylaminoiminomethyl, (C2-C8)- Alkenyloxyiminomethyl, Arylaminoiminomethyl, Arylsulfonylaminoiminomethyl, Heteroaryl-(Ci-C8)-alkyl, Heterocyclyl-(Ci-C8)-alkyl, Bis [(C 1 -C 8 ) -alkyl] aminocarbonyl- (C 1 -C 8 ) -alkyl, (C: C 8 ) -cycloalkylaminocarbonyl- (C 1 -C 8 ) -alkyl, aryl- (C 1 -C 8 ) -alkylaminocarbonyl- (Ci -C 8) alkyl, heteroaryl (Ci-C8) - alkylaminocarbonyl (CRC8) alkyl, cyano (Ci-C8) alkylaminocarbonyl (-C 8) - alkyl, (Ci-C 8) -Haloaikylaminocarbonyl - (Ci-C 8) alkyl, (C2-C8) alkynyl (dC 8) - alkylaminocarbonyl (Ci-C8) alkyl, (C 3 -C 8) -cycloalkyl- (Ci-C 8 ) - alkylaminocarbonyl (CRC8) alkyl, (Ci-C 8) -Alkoxycarbonylaminocarbonyl- (Ci-Ce) alkyl, aryl (Ci-C8) -alkoxycarbonylaminocarbonyl- (Ci-C8) alkyl, (Ci-C 8 ) - alkoxycarbonyl- (C 1 -C 8 ) -alkylaminocarbonyl, hydroxycarbonyl- (C 1 -C 8 ) -alkylaminocarbonyl, aryl- (C 1 -C 8 ) -alkoxycarbonyl- (C 1 -C 8) -alkylaminocarbonyl, (C 1 -C 8) -alkoxycarbonyl-heterocyclyl-N -carbonyl, (Ci-C8) alkoxycarbonyl (CI-C8) alkyl-heterocyclylidenaminocarbonyl, (Ci-C 8) - Alkoxycarbonylheterocyclyliden- (CRC8) alkylaminocarbonyl (Ci-C8) - alkoxycarbonyl, (Ci-C8 ) alkyl ((Ci-C8) alkyl) aminocarbonyl, (Ci-C8) - alkoxycarbonyl (C 3 -C 8) - cycloalkylideneaminocarbonyl, heterocyclyl-N-carbonyl, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkylaminocarbonyl, aminocarbonyl- (C 1 -C 8 ) -alkylaminocarbonyl, (C 1 -C 8 ) -alkylaminocarbonyl- (C 1 -C 8 -alkyl) 8) -alkylaminocarbonyl, (C3-Cs) -Cycloalkylaminocarbonyl- (Ci-C8) alkylaminocarbonyl, (Ca-Cs) - cycloalkyl- (Ci-C 8) -alkylaminocarbony !, (C 3 -C 8) -cycloalkyl- ( Ci-C8) - alkylaminocarbonyl (Ci-C8) alkyl, (C 3 -C 8) -Cycloafkyl- (Ci-C8) - alkylaminocarbonyl (Ci-C8) alkylaminocarbonyl, (C2-C8) Alkenyl- (C 1 -C 8 ) -alkylaminocarbonyl, (C 2 -C 8 ) -alkenylaminocarbonyl- (C 1 -C 8 ) -alkyl, (C 2 -C 8 ) -alkenyl- (C 1 -C 8 ) -alkylaminocarbonyl- (C 1 -C 8 ) alkyl, (C 1 -C 6 ) -alkylcarbonyl, (C 3 -C 8 ) -cycloalkylcarbonyl, arylcarbonyl, formyl, hydroxyiminomethyl, Aminoiminomethyl, (C 1 -C 8) -alkoxyiminomethyl, (C 1 -C 8) -alkylaminoiminomethyl, bis [(C 1 -C 8) -alkyl] aminoiminomethyl, (Ca-CeJ-cycloalkoxyiminomethyl, (Ca-Ce) -cycloacyl- (C 1 -C 8) alkoximinomethyl, aryloximinomethyl, aryl- (C 1 -C 8) -alkoxyiminomethyl, aryl- (C 1 -C 8) -alkylaminoiminomethyl, (C 2 -C 8) -alkenyloxyiminomethyl, arylaminoiminomethyl, arylsulfonylaminoiminomethyl, heteroaryl- (C 1 -C 8) -alkyl, heterocyclyl ( C 1 -C 8 ) -alkyl,
Hydroxycarbonylheterocyclyl, (CrC8)-Alkoxycarbonylheterocyclyl, (C2-Cs)- Alkenyloxycarbonylheterocyclyl, (C2-C8)-Alkenyl-(Ci-Ce)- alkoxycarbonylheterocyclyl, Aryl-(Ci-C8)-alkoxycarbonylheterocyclyl, (C3-Cs)- Cycloalkoxycarbonylheterocyclyl, (C3-C8)-Cycloalkyl-(Ci-C-8)- alkoxycarbonylheterocyclyl, Aminocarbonylheterocyclyl, (d-Ce)- Alkylaminocarbonylheterocyclyl, Bis[(CrC8)-Alkyl]aminocarbonylheterocyclyl, (C3-C8)-Cycloalkylaminocarbonylheterocyclyl, Aryl-(Ci-Cs)- alkylaminocarbonylheterocyclyl, (C2-C8)-Alkenylaminocarbonylheterocyclyl, Hydroxycarbonylheterocyclyl-(CrC8)-alkyl, (Ci-C8)-Alkoxycarbonylheterocyclyl- (Ci-C8)-alkyl, Hydroxycarbonyl-(C3-C8)-cycloalkyl-(Ci-C8)-alkyl, (d-Ce)- Alkoxycarbonyl-(C3-C8)-cycloalkyl-(CrC8)-alkyl, Hydroxyaminocarbonyl, Hydroxycarbonylheterocyclyl, (C 1 -C 8) -alkoxycarbonylheterocyclyl, (C 2 -C 5) -alkenyloxycarbonylheterocyclyl, (C 2 -C 8) -alkenyl- (C 1 -C 4) -alkoxycarbonylheterocyclyl, aryl- (C 1 -C 8) -alkoxycarbonylheterocyclyl, (C 3 -C 5) -cycloalkoxycarbonylheterocyclyl, (C 3 -C 8) -cycloalkyl- (C 1 -C 8) -alkoxycarbonyl-heterocyclyl, aminocarbonyl-heterocyclyl, (d-Ce) -alkylaminocarbonyl-heterocyclyl, bis [(C 1 -C 8) -alkyl] -aminocarbonyl-heterocyclyl, (C 3 -C 8) -cycloalkylaminocarbonyl-heterocyclyl, aryl- (Ci -Cs) - alkylaminocarbonylheterocyclyl, (C 2 -C 8 ) -alkenylaminocarbonylheterocyclyl, hydroxycarbonylheterocyclyl- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkoxycarbonylheterocyclyl- (C 1 -C 8 ) -alkyl, hydroxycarbonyl- (C 3 -C 8) -cycloalkyl- (C 1 -C 8 ) -alkyl, (d-Ce) -alkoxycarbonyl- (C 3 -C 8 ) -cycloalkyl- (C 1 -C 8 ) -alkyl, hydroxyaminocarbonyl,
(Ci-C8)-Alkoxyaminocarbonyl, Aryl-(Ci-C8)-alkoxyaminocarbonyl, Heterocyclyl, (Ci-C8)-Alkylcarbonyloxy, Arylcarbonyioxy, Heteroarylcarbonyloxy, (Ca-Ce)- Cycloalkylcarbonyloxy, (Ci-C-8)-Alkoxycarbonyloxy, (C2-C8)- Alkenyloxycarbonyloxy steht, (C 1 -C 8) -alkoxyaminocarbonyl, aryl- (C 1 -C 8) -alkoxyaminocarbonyl, heterocyclyl, (C 1 -C 8) -alkylcarbonyloxy, arylcarbonyloxy, heteroarylcarbonyloxy, (C 1 -C 6) -cycloalkylcarbonyloxy, (C 1 -C 8) -alkoxycarbonyloxy, (C2-C8) - Alkenyloxycarbonyloxy stands,
R7, R8 , R9 und R10 unabhängig voneinander für Wasserstoff, Halogen, Nitro, Amino, Cyano, (CrC8)-Alkyl, Aryl, Heteroaryi, (C3-C8)-Cycloalkyl, (C4-C8)-Cycloalkenyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (C2-C8)-Alkenyl-(Ci-C8)-alkyl, (C2-C8)-Alkinyl- (Ci-C8)-alkyl, Hydroxy, (Ci-C8)-Alkoxy, (Ci-C8)-Alkoxy-(Ci-C8)-alkoxy, (d-Ce)- Alkoxy-(Ci-C8)-alkyl, Hydroxy-(Ci-C8)-alkyl, (Ci-C8)-Haloalkoxy, (Ci-Ce)- Haloalkyl, (C2-C8)-Haloalkenyl, (C2-C8)-Haloalkinyl, (Ci-Ce)-Haloalkoxy-(Ci-Ce)- alkyl, (Ci-C8)-Alkoxy-(Ci-C8)-haloalkyl, (Ci-C8)-Haloalkoxy-(Ci-C8)-haloalkyl, Hydrothio, (Ci-C8)-Alkylthio, (CrC8)-Haloalkylthio, (Ci-C8)-Alkylthio-(Ci-C8)- alkyl, (Ci-C8)-Haloalkylthio-(Ci-C8)-alkyl, (Ci-Cö)-Alkylamino, Bis[(Ci-Ce)- alkyl]amino, (C2-C8)-Alkenylamino, (Ca-CeJ-Cycloalkylamino, (d-d)- Alkylcarbonylamino, (Ca-dJ-Cycloalkylcarbonylamino, Arylcarbonylamino, Heteroarylcarbonylamino, Formylamino, (d-CsJ-Haloalkylcarbonylamino,
(Ci-C8)-Alkoxycarbonylamino, (Ci-C8)-Alkylaminocarbonylamino, (C-i-Cs)- Alkyl[(Ci-C8)-Alkyl]aminocarbonylamino, (Ci-C8)-Alkylsulfonylamino, (Ca-Cs)- Cycloalkylsulfonylamino, Arylsulfonylamino, Hetarylsulfonylamino, Sulfonyl- (CrC8)-haloalkylamino, Amino-(Ci-C8)-alkylsulfonyl, Amino-(CrC8)- haloalkylsulfonyl, (CrC8)-Alkylaminosulfonyl, Bis[(Ci-C8)-alkyl]aminosulfonyl, (Ca-CsJ-Cycloalkylaminosulfonyl, (CrC8)-Haloalkylaminosulfonyl, R 7, R 8, R 9 and R 10 are independently hydrogen, halogen, nitro, amino, cyano, (CrC 8) alkyl, aryl, heteroaryl, (C 3 -C 8) cycloalkyl, (C 4 -C 8) -cycloalkenyl, (C 2 -C 8) alkenyl, (C 2 -C 8) -alkynyl, (C2-C8) alkenyl (Ci-C 8) alkyl, (C 2 -C 8) Alkynyl (C 1 -C 8 ) -alkyl, hydroxy, (C 1 -C 8 ) -alkoxy, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkoxy, (d-Ce) -alkoxy- Ci-C 8) alkyl, hydroxy (Ci-C 8) alkyl, (Ci-C8) -haloalkoxy, (Ci-Ce) - haloalkyl, (C 2 -C 8) -haloalkenyl, (C 2 - C 8 ) -haloalkynyl, (C 1 -C 6 ) -haloalkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) -haloalkoxy- Ci-C 8) haloalkyl, Hydrothio, (Ci-C8) alkylthio, (CrC 8) haloalkylthio, (Ci-C8) alkylthio (Ci-C8) - alkyl, (Ci-C 8) -Haloalkylthio- (Ci-C 8) alkyl, (Ci-C ö) alkylamino, bis [(Ci-Ce) - alkyl] amino, (C2-C8) -alkenylamino, (Ca-CeJ-cycloalkylamino, (dd ) - alkylcarbonylamino, (Ca-dJ-cycloalkylcarbonylamino, arylcarbonylamino, heteroarylcarbonylamino, formylamino, (d-CsJ-haloalkylcarbonylamino, (C 1 -C 8) -alkoxycarbonylamino, (C 1 -C 8) -alkylaminocarbonylamino, (C 1 -C 8) -alkyl [(C 1 -C 8) -alkyl] aminocarbonylamino, (C 1 -C 8) -alkylsulfonylamino, (C 1 -C 5) -cycloalkylsulfonylamino, Arylsulfonylamino, hetarylsulfonylamino, sulfonyl- (C 1 -C 8) -haloalkylamino, amino- (C 1 -C 8) -alkylsulfonyl, amino- (C 1 -C 8) -haloalkylsulfonyl, (C 1 -C 8) -alkylaminosulfonyl, bis [(C 1 -C 8) -alkyl] -aminosulfonyl, (Ca -CsJ-cycloalkylaminosulfonyl, (CrC8) -haloalkylaminosulfonyl,
Heteroarylaminosulfonyl, Arylaminosulfonyl, Aryl-(Ci-C8)-alkylaminosulfonyl, (Ci-C8)-Alkylsulfonyl, (Ca-CaJ-Cycloalkylsulfonyl, Arylsulfonyl, Hydroxycarbonyl, (Ci-C8)-Alkoxycarbonyl, (C:3-C8)-Cycloalkoxycarbonyl, (Ca-CeJ-Cycloalkyl- (Ci-C8)-alkoxycarbonyl, Aryloxycarbonyl, Aryl-(Ci-C8)-alkoxycarbonyl, (C2-C-8)- Alkenyloxycarbonyl, (C2-C8)-Alkinyloxycarbonyl, Aminocarbonyl, (Ci-Cs)- Alkylaminocarbonyl, Bis[(CrC8)-alkyl]aminocarbonyl, (d-C8)-Alkyl[(Ci-C8)- Alkyl]aminocarbonyl, (Ci-C8)-Alkyl[(Ci-C8)-Alkoxy]aminocarbonyl, (C2-Cs)- Alkenylaminocarbonyl, (C3-C8)-Cycloalkylaminocarbonyl, Arylaminocarbonyl, Aryl-(Ci-C8)-alkylaminocarbonyl stehen, Heteroarylaminosulfonyl, arylaminosulfonyl, aryl- (Ci-C8) -alkylaminosulfonyl, (Ci-C8) -alkylsulfonyl, (Ca-CaJ-cycloalkylsulfonyl, arylsulfonyl, hydroxycarbonyl, (Ci-C8) -alkoxycarbonyl, (C: 3-C8) -cycloalkoxycarbonyl , (C 1 -C 12 -cycloalkyl- (C 1 -C 8) -alkoxycarbonyl, aryloxycarbonyl, aryl- (C 1 -C 8) -alkoxycarbonyl, (C 2 -C-8) -alkenyloxycarbonyl, (C 2 -C 8) -alkynyloxycarbonyl, aminocarbonyl, (Ci -Cs) - alkylaminocarbonyl, bis [(C 1 -C 8) -alkyl] aminocarbonyl, (C 1 -C 8) -alkyl [(C 1 -C 8) -alkyl] aminocarbonyl, (C 1 -C 8) -alkyl [(C 1 -C 8) -alkoxy] aminocarbonyl, (C 2 -C 5) - alkenylaminocarbonyl, (C 3 -C 8) -cycloalkylaminocarbonyl, arylaminocarbonyl, aryl- (C 1 -C 8) -alkylaminocarbonyl,
A1, A2, A3 und A4 gleich oder verschieden sind und unabhängig voneinander für NA 1 , A 2 , A 3 and A 4 are the same or different and are independently N
(Stickstoff) oder die Gruppierungen C-H, C-CH3, C-F, C-Cl, C-Br, C-l, C-OCF3, C-OCH3, C-CF3, C-CO2H, C-CO2CH3 stehen, wobei jedoch in keinem Fall mehr als zwei N-Atome benachbart sind, (Nitrogen) or the groupings CH, C-CH 3, CF, C-Cl, C-Br, CI, C-OCF3, C-OCH3, C-CF3, C-CO2H, C-CO2CH3 are, however, in no more than two N-atoms are adjacent,
R11 und R12 unabhängig voneinander für Wasserstoff, Halogen, (Ci-Cs)-Alkyl, Aryl, Heteroaryl, Heterocyclyl, (C3-C8)-Cycloalkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (CrC8)-Alkoxy, (Ci-C8)-Alkoxy-(Ci-C8)-alkyl, Aryloxy-(Ci-C8)-alkyl, (Ci-C8)- Haloalkoxy, (Ci-C8)-Haloalkyl, (Ci-C8)-Haloalkoxy-(Ci-C8)-alkyl, (Ci-C8)-Alkoxy- (CrC8)-haloalkyl, (Ci-C8)-Haloalkoxy-(Ci-C8)-haloalkyl, (CrC8)-Alkylthio, R 11 and R 12 independently of one another represent hydrogen, halogen, (C 1 -C 5 ) -alkyl, aryl, heteroaryl, heterocyclyl, (C 3 -C 8 ) -cycloalkyl, (C 2 -C 8 ) -alkenyl, (C 2 - C 8 ) -alkynyl, (C 1 -C 8 ) -alkoxy, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, aryloxy- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkoxy , (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) -haloalkoxy- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) Haloalkoxy- (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) -alkylthio,
(Ci-C8)-Haloalkylthio, (Ci-C8)-Alkylthio-(Ci-C8)-alkyl, Hydroxycarbonyl, (Ci-C8)- Alkoxycarbonyl, (Cs-CeJ-Cycloalkoxycarbonyl, (C3-C8)-Cycloalkyl-(Ci-C8)- alkoxycarbonyl, Aryloxycarbonyl, Aryl-(Ci-C8)-alkoxycarbonyl, (C2-C8)- Alkenyloxycarbonyl, (C2-C8)-Alkinyloxycarbonyl, Aminocarbonyl, (Ci-Cs)- Alkylaminocarbonyl, Bis[(Ci-C8)-alkyl]aminocarbonyl, (Ci-C8)-Alkyl[(Ci-C8)- Alkyljaminocarbonyl, (Ci-C8)-Alkyl[(CrC8)-Alkoxy]aminocarbonyl, (C2-C8)- Alkenylaminocarbonyl, (Cs-Ce Cycloalkylaminocarbonyl, Arylaminocarbonyl, Aryl-(CrC8)-alkylaminocarbonyl stehen,
A5 für S (Schwefel), O (Sauerstoff) oder die Gruppierungen N-H, N-CH3, N-CH2CH3, N- CH(CH3)2, N-C02t-Bu, N-Aryl, N-Heteroaryl, N-Heterocyclyl steht, (C 1 -C 8 ) -haloalkylthio, (C 1 -C 8 ) -alkylthio (C 1 -C 8 ) -alkyl, hydroxycarbonyl, (C 1 -C 8 ) -alkoxycarbonyl, (C 1 -C 12 -cycloalkoxycarbonyl, (C 3 -C 8 ) - Cycloalkyl- (C 1 -C 8) -alkoxycarbonyl, aryloxycarbonyl, aryl- (C 1 -C 8) -alkoxycarbonyl, (C 2 -C 8) -alkenyloxycarbonyl, (C 2 -C 8) -alkynyloxycarbonyl, aminocarbonyl, (C 1 -C 8) -alkylaminocarbonyl, bis [ (C 1 -C 8) -alkyl] aminocarbonyl, (C 1 -C 8) -alkyl [(C 1 -C 8) -alkyl] aminocarbonyl, (C 1 -C 8) -alkyl [(C 1 -C 8) -alkoxy] -aminocarbonyl, (C 2 -C 8) -alkenylaminocarbonyl, (C 1 -C 6 -cycloalkylaminocarbonyl, arylaminocarbonyl, aryl- (C 1 -C 8) -alkylaminocarbonyl, A 5 for S (sulfur), O (oxygen) or the groupings NH, N-CH 3 , N-CH 2 CH 3 , N-CH (CH 3 ) 2, N-CO 2 t-Bu, N-aryl, N-heteroaryl , N-heterocyclyl,
R14, R17 und R18 unabhängig voneinander für Wasserstoff, (d-C8)-Alkyl, Halogen, (C3-C8)-Cycloalkyl, Aryl, Heteroaryl, Heterocyclyl, (C2-C8)-Alkenyl, (C2-C8)- Alkenyl-(CrC8)-alkyl, Aryl-(Ci-C8)-alkyl, (d-C8)-Alkoxy, (Ci-C8)-Alkoxy-(Ci-C8)- alkoxy, (Ci-C8)-Alkoxy-(CrC8)-alkyl, Hydroxy, (Ci-C8)-Haloalkyl, (Ci-C8)- Haloalkylthio stehen oder und R17 mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls weiter substituierten 5 bis 7-gliedrigen Ring bilden, A6, A7 gleich oder verschieden sind und unabhängig voneinander für O (Sauerstoff), S (Schwefel), N-H, N-OCH3, N-CH3 oder die Gruppierung CR15R16 stehen, wobei jedoch in keinem Fall zwei N-, O- oder S-Atome benachbart sind, und wobei R15 und R16 in der Gruppierung CR15R16 jeweils gleiche oder verschiedene R 14 , R 17 and R 18 independently of one another represent hydrogen, (C 1 -C 8 ) -alkyl, halogen, (C 3 -C 8 ) -cycloalkyl, aryl, heteroaryl, heterocyclyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8) - alkenyl (-C 8) alkyl, aryl (Ci-C8) alkyl, (dC 8) alkoxy, (Ci-C 8) alkoxy (Ci-C 8) - alkoxy, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, hydroxy, (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) -haloalkylthio or and R 17 having the atoms to which they are attached, form a fully saturated or partially saturated, optionally further substituted 5 to 7-membered ring, A 6 , A 7 are identical or different and independently of one another O (oxygen), S (sulfur), NH, N-OCH 3, N-CH 3 or the grouping CR 15 R 16 , but in no case are two N, O or S atoms adjacent, and wherein R 15 and R 16 in the grouping CR 15 R 16 are each the same or different
Bedeutungen gemäß der nachstehenden Definition haben und Have meanings as defined below and
R15 und R16 unabhängig voneinander für Wasserstoff, Halogen, (CrCs)-Alkyl, Aryl, Heteroaryl, Heterocyclyl, (C3-C8)-Cycloalkyl, (C2-C8)-Alkenyl, (Ci-C8)-Alkoxy, (Ci-C8)-Alkoxy-(CrC8)-alkyl, Aryloxy-(d-C8)-alkyl, (d-C8)-Haloalkoxy, (d-C8)- Haloalkyl, (Ci-C8)-Haloalkoxy(CrC8)-alkyl. (Ci-C8)-Alkoxy-(d-C8)-haloalkyl, (CrC8)-Haloalkoxy-(Ci-C8)-haloalkyl, (Ci-Cs)-Alkylthio, (d-C8)-Haloalkylthio,R 15 and R 16 are independently hydrogen, halogen, (CRCs) alkyl, aryl, heteroaryl, heterocyclyl, (C 3 -C 8) cycloalkyl, (C2-C8) alkenyl, (Ci-C 8) - alkoxy, (Ci-C 8) alkoxy (CrC 8) alkyl, aryloxy (dC 8) alkyl, (dC 8) -haloalkoxy, (dC 8) - haloalkyl, (Ci-C8) haloalkoxy ( CrC 8 ) alkyl. (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) -haloalkoxy- (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) -alkylthio, (C 1 -C 8 ) -haloalkylthio,
(d-C8)-Alkylthio-(Ci-C8)-alkyl, Hydroxycarbonyl, (d-C8)-Alkoxycarbonyl, (C3-C8)-Cycloalkoxycarbonyl, (C3-C8)-Cycloalkyl-(Ci-C8)-alkoxycarbonyl, Aryloxycarbonyl, Aryl-(Ci-C8)-alkoxycarbonyl, (C2-C8)-Alkenyloxycarbonyl, (C2-C8)-Alkinyloxycarbonyl, Aminocarbonyl, (Ci-Cs)-Alkylaminocarbonyl, Bis[(CrC8)-alkyl]aminocarbonyl, (Ci-C8)-Alkyl[(CrC8)-Alkyl]aminocarbonyl,(dC 8) alkylthio (Ci-C8) alkyl, hydroxycarbonyl, (DC 8) -alkoxycarbonyl, (C 3 -C 8) -cycloalkoxycarbonyl, (C 3 -C 8) -cycloalkyl- (Ci-C 8 ) alkoxycarbonyl, aryloxycarbonyl, aryl- (C 1 -C 8 ) -alkoxycarbonyl, (C 2 -C 8 ) -alkenyloxycarbonyl, (C 2 -C 8 ) -alkynyloxycarbonyl, aminocarbonyl, (C 1 -C 8 ) -alkylaminocarbonyl, bis [(CrC 8 ) -alkyl] aminocarbonyl, (C 1 -C 8 ) -alkyl [(C 1 -C 8 ) -alkyl] aminocarbonyl,
(Ci-C8)-Alkyl[(Ci-C8)-Alkoxy]aminocarbonyl, (C2-C8)-Alkenylaminocarbonyl, (C3-C8)-Cycloalkylaminocarbonyl, Arylaminocarbonyl, Aryl-(d-C8)- alkylaminocarbonyl, Amino, (d-C8)-Alkylamino, (C3-C8)-Cycloalkylamino, Bis- [(Ci-C8)-Alkyl]amino stehen,
R19, R20, R22 und R23 unabhängig voneinander für Wasserstoff, (Ci-C8)-Alkyl, Halogen, (C3-C8)-Cycloalkyl, Aryl, Heteroaryl, Heterocyclyl, (C2-C8)-Alkenyl, Aryl-(d-Ce)- alkyl, (CrC8)-Alkoxy, (Ci-C8)-Alkoxy-(Ci-C8)-alkoxy, (Ci-C8)-Alkoxy-(Ci-C8)- alkyl, (Ci-Cs)-Haloalkyl stehen, (Ci-C 8) alkyl [(Ci-C 8) alkoxy] aminocarbonyl, (C2-C8) -Alkenylaminocarbonyl, (C 3 -C 8) cycloalkylaminocarbonyl, arylaminocarbonyl, aryl (dC 8) - alkylaminocarbonyl, Amino, (C 1 -C 8 ) -alkylamino, (C 3 -C 8 ) -cycloalkylamino, bis- [(C 1 -C 8 ) -alkyl] -amino, R 19, R 20, R 22 and R 23 are independently hydrogen, (Ci-C 8) alkyl, halogen, (C 3 -C 8) cycloalkyl, aryl, heteroaryl, heterocyclyl, (C 2 -C 8) Alkenyl, aryl- (d-Ce) -alkyl, (C 1 -C 8 ) -alkoxy, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkoxy, (C 1 -C 8 ) -alkoxy- (ci) C 8 ) -alkyl, (C 1 -C 5) -haloalkyl,
A8 für O (Sauerstoff), S (Schwefel), N-H, N-CH3, N-OCH3 oder die Gruppierung CHR21 steht und wobei R21 in der Gruppierung CHR21 die Bedeutung gemäß der nachstehenden Definition hat, A 8 is O (oxygen), S (sulfur), NH, N-CH 3 , N-OCH 3 or the moiety CHR 21 , and wherein R 21 in the moiety CHR 21 has the meaning as defined below,
R21 für Wasserstoff, Halogen, (d-C8)-Alkyl, Aryl, Heteroaryl, Heterocyclyl, (C;i-C8)- Cycloalkyl, (C2-C8)-Alkenyl, (Ci-Cs)-Alkoxy, (CrC8)-Alkoxy-(Ci-C8)-alkyl, Aryloxy-(Ci-C8)-alkyl, (Ci-Cs)-Haloalkoxy, (d-C8)-Haloalkyl, (d-C8)-Alkoxy- (Ci-Cs)-haloalkyl, (Ci-C8)-Haloalkoxy-(CrC8)-haloalkyl, (d-C8)-Alkylthio, R 21 is hydrogen, halogen, (DC 8) alkyl, aryl, heteroaryl, heterocyclyl, (C; iC 8) - cycloalkyl, (C 2 -C 8) alkenyl, (Ci-Cs) alkoxy, (CrC 8 ) alkoxy (Ci-C 8) alkyl, aryloxy (Ci-C8) alkyl, (Ci-Cs) haloalkoxy, (dC 8) -haloalkyl, (dC 8) alkoxy- (Ci-Cs ) -haloalkyl, (C 1 -C 8 ) -haloalkoxy- (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) -alkylthio,
(Ci-C8)-Haloalkylthio, (Ci-C8)-Alkylthio(d-C8)-alkyl, Hydroxycarbonyl, (Ci-Ce)- Alkoxycarbonyl, (C3-C8)-Cycloalkoxycarbonyl, Aryl-(Ci-C8)-alkoxycarbonyl, (C2-C8)-Alkenyloxycarbonyl, (C2-C8)-Alkinyloxycarbonyl, Aminocarbonyl, (Ci-C8) haloalkylthio, (Ci-C8) alkylthio (dC 8) -alkyl, hydroxycarbonyl, (Ci-Ce) - alkoxycarbonyl, (C3-C8) -cycloalkoxycarbonyl, aryl (Ci-C 8 ) alkoxycarbonyl, (C 2 -C 8 ) -alkenyloxycarbonyl, (C 2 -C 8 ) -alkynyloxycarbonyl, aminocarbonyl,
(Ci-C8)-Alkylaminocarbonyl, Bis[(Ci-C8)-alkyl]aminocarbonyl, (Ci-C8)- Alkyl[(Ci-C8)-Alkyl]aminocarbonyl, (Ci-C8)-Alkyl[(Ci-C8)-Alkoxy]aminocarbonyl, (C2-C8)-Alkenylaminocarbonyl, (C3-C8)-Cycloalkylaminocarbonyl, (Ci-C 8) alkylaminocarbonyl, bis [(Ci-C 8) alkyl] aminocarbonyl, (Ci-C 8) - alkyl [(Ci-C 8) alkyl] aminocarbonyl, (Ci-C 8) -alkyl [(C 1 -C 8 ) -alkoxy] aminocarbonyl, (C 2 -C 8 ) -alkenylaminocarbonyl, (C 3 -C 8 ) -cycloalkylaminocarbonyl,
Arylaminocarbonyl, Aryl-(Ci-C8)-alkylaminocarbonyl, Amino, (Ci-C8)-Alkylamino, (C3-C8)-Cycloalkylamino, Bis[(Ci-C8)-Alkyl]amino steht, Arylaminocarbonyl, aryl- (C 1 -C 8 ) -alkylaminocarbonyl, amino, (C 1 -C 8 ) -alkylamino, (C 3 -C 8 ) -cycloalkylamino, bis [(C 1 -C 8 ) -alkyl] -amino,
R24, R25, R26, R28, R29 und R30 unabhängig voneinander für Wasserstoff, (Ci-C8)-Alkyl, Halogen, (C3-C8)-Cycloalkyl, Aryl, Heteroaryl, Heterocyclyl, (C2-C8)-Alkenyl, (Ci-Cs)-Alkoxy, (Ci-C8)-Alkoxy-(Ci-C8)-alkoxy, (Ci-C8)-Alkoxy-(Ci-C8)-alkyl, (Ci-C8)-Haloalkyl, (Ci-C8)-Alkylthio, (Ci-C8)-Haloalkylthio stehen, R 24, R 25, R 26, R 28, R 29 and R 30 are independently hydrogen, (Ci-C 8) alkyl, halogen, (C 3 -C 8) cycloalkyl, aryl, heteroaryl, heterocyclyl, ( C 2 -C 8 -alkenyl, (C 1 -C 5) -alkoxy, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkoxy, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) - alkyl, (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) -alkylthio, (C 1 -C 8 ) -haloalkylthio,
A9 für O (Sauerstoff), S (Schwefel), N-H, N-CH3, N-OCH3 oder die Gruppierung CHR27 steht und wobei R27 in der Gruppierung CHR27 die Bedeutung gemäß der nachstehenden Definition hat und A 9 is O (oxygen), S (sulfur), NH, N-CH 3, N -OCH 3 or the moiety CHR 27 and wherein R 27 in the moiety CHR 27 has the meaning as defined below and
R27 für Wasserstoff, Halogen, (Ci-C8)-Alkyl, Aryl, Heteroaryl, Heterocyclyl, (C3-C8)- Cycloalkyl, (C2-C8)-Alkenyl, (d-C8)-Alkoxy, (Ci-C8)-Alkoxy-(CrC8)-alkyl,
Aryloxy-(Ci-C8)-alkyl, (Ci-C8)-Haloalkoxy, (Ci-C8)-Haloalkyl, (Ci-Ce)-Alkylthio, (d-CsJ-Haloalkylthio, Hydroxycarbonyl, (Ci-C8)-Alkoxycarbonyl, (Ca-Ce)- Cycloalkoxycarbonyl, Aryl-(Ci-C8)-a!koxycarbonyl, (C2-C8)-Alkenyloxycarbonyl, (C2-C8)-Alkinyloxycarbonyl, Aminocarbonyl, (Ci-C8)-Alkylaminocarbonyl, Bis[(Ci-C8)-alkyl]aminocarbonyl, (Ci-C8)-Alkyl[(CrC8)-Alkyl]aminocarbonyl, (Ci-C8)-Alkyl[(CrC8)-Alkoxy]aminocarbonyl, (C2-C8)-Alkenylaminocarbonyl, (Ca-Ce Cycloalkyiaminocarbonyl, Arylaminocarbonyl, Aryl-(d-C8)- alkylaminocarbonyl, Amino, (Ci-CsJ-Alkyiamino, (Ca-CsJ-Cycloalkylamino, Bis[(Ci-C8)-Alkyl]amino steht. R 27 is hydrogen, halogen, (Ci-C 8) alkyl, aryl, heteroaryl, heterocyclyl, (C 3 -C 8) - cycloalkyl, (C 2 -C 8) alkenyl, (DC 8) alkoxy, ( C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, Aryloxy- (Ci-C 8 ) -alkyl, (Ci-C 8 ) -haloalkoxy, (Ci-C 8 ) -haloalkyl, (Ci-Ce) -alkylthio, (d-CsJ-haloalkylthio, hydroxycarbonyl, (Ci-C8 ) Alkoxycarbonyl, (Ca-Ce) - cycloalkoxycarbonyl, aryl- (C 1 -C 8) -alkoxycarbonyl, (C 2 -C 8) -alkenyloxycarbonyl, (C 2 -C 8) -alkynyloxycarbonyl, aminocarbonyl, (C 1 -C 8) -alkylaminocarbonyl, Bis [(C 1 -C 8) -alkyl] aminocarbonyl, (C 1 -C 8) -alkyl [(C 1 -C 8) -alkyl] aminocarbonyl, (C 1 -C 8) -alkyl [(C 1 -C 8) -alkoxy] -aminocarbonyl, (C 2 -C 8) - Alkenylaminocarbonyl, (C 1 -C 6 cycloalkylaminocarbonyl, arylaminocarbonyl, aryl- (C 1 -C 8 ) -alkylaminocarbonyl, amino, (C 1 -C 5 -alkylamino, (C 1 -C 8 -cycloalkylamino, bis [(C 1 -C 8 ) -alkyl] -amino.
Besonders bevorzugt ist die erfindungsgemäße Verwendung von Verbindungen der aligemeinen Formel (I), worin Particular preference is given to the use according to the invention of compounds of the general formula (I) in which
[X-Y] für die Gruppierungen [X-Y] for the groupings
[X-YJ1 und [X-Y!2 steht. [X-YJ1 and [XY! 2 stands.
Q für die Gruppierungen Q-1 bis Q-6 Q for the groupings Q-1 to Q-6
Q-1 Q-2 Q-3 Q-1 Q-2 Q-3
Q-4 Q-5 und Q-6 steht, wobei R7, R8, R9, R10, R11, R12, R13, R14, R17, R18, R19, R20, R22, R23, R24, R25, R26, R28, R29 und R30 und A1 bis A9 jeweils die Bedeutung gemäß der
nachstehenden Definitionen haben und wobei der Pfeil für eine Bindung zur jeweiligen Gruppierung C-R6 in der allgemeinen Formel (I) steht, Q-4 Q-5 and Q-6 wherein R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 17 , R 18 , R 19 , R 20 , R 22 , R 23 , R 24 , R 25 , R 26 , R 28 , R 29 and R 30 and A 1 to A 9 are each as defined in the have the following definitions and wherein the arrow for a bond to the respective grouping is CR 6 in the general formula (I),
R1 für (Ci-C7)-Alkyl, (C3-C7)-Cycloalkyl, (C4-C7)-Cycloalkenyl, (C2-C7)-Alkenyl, (C2-C7)-Alkinyl, (C2-C7)-Alkenyl-(Ci-C7)-alkyl, (C2-C7)-Alkinyl-(Ci-C7)-alkyl, (Ci-C7)-Alkoxy-(Ci-C7)-alkyl, Hydroxy-(Ci-C7)-alkyl, (Ci-C7)-Haloalkyl, (C2-C7)- Haloalkenyl, (C2-C7)-Haloalkinyl, (Ci-C7)-Haloalkoxy-(Ci-C7)-alkyl, (C1-C7)- Alkoxy-(Ci-C7)-haloalkyl, (Ci-C7)-Haloalkoxy-(CrC7)-haloalkyl, (C1-C7)- Alkylthio-(Ci-C7)-alkyl, (Ci-C7)-Haloalkylthio-(Ci-C7)-alkyl steht, R 1 is (C 1 -C 7 ) -alkyl, (C 3 -C 7 ) -cycloalkyl, (C 4 -C 7 ) -cycloalkenyl, (C 2 -C 7 ) -alkenyl, (C 2 -C 7 ) - alkynyl, (C 2 -C 7) (alkenyl (Ci-C7) alkyl, (C 2 -C 7) alkynyl (Ci-C7) alkyl, (Ci-C7) alkoxy Ci-C 7) alkyl, hydroxy (Ci-C7) alkyl, (Ci-C7) haloalkyl, (C2-C7) - haloalkenyl, (C 2 -C 7) haloalkynyl, (Ci-C 7 ) haloalkoxy- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -haloalkoxy- (C 1 -C 7 ) -haloalkyl, C7) -alkylthio (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -haloalkylthio (C 1 -C 7 ) -alkyl,
R2, R3 und R4 unabhängig voneinander für Wasserstoff, Halogen, (Ci-C7)-Alkyl, R 2 , R 3 and R 4 independently of one another represent hydrogen, halogen, (C 1 -C 7 ) -alkyl,
(C3-C7)-Cycloalkyl, (C4-C7)-Cycloalkenyl, (C2-C7)-Alkenyl, (C2-C7)-Alkinyl, (C2-C7)-Alkenyl-(CrC7)-alkyl, (C2-C7)-Alkinyl-(Ci-C7)-alkyl, (d-C7)-Alkoxy- (CrC7)-alkyl, Hydroxy-(Ci-C7)-alkyl, (Ci-C7)-Haloalkyl, (C2-C7)-Haloalkenyl, (C2-C7)-Haloalkinyl, (Ci-C7)-Haloalkoxy-(Ci-C7)-alkyl, (Ci-C7)-Alkoxy-(Ci-C7)- haloalkyl, (CrC7)-Haloalkoxy-(Ci-C7)-haloalkyl, (d-C7)-Alkylthio-(Ci-C7)-alkyl, (CrC7)-Haloalkylthio-(Ci-C7)-alkyl stehen, (C 3 -C 7 ) -cycloalkyl, (C 4 -C 7 ) -cycloalkenyl, (C 2 -C 7 ) -alkenyl, (C 2 -C 7 ) -alkynyl, (C 2 -C 7 ) -alkenyl- (-C 7) alkyl, (C 2 -C 7) alkynyl (Ci-C7) alkyl, (dC 7) alkoxy (CrC 7) alkyl, hydroxy (Ci-C7) alkyl , (Ci-C7) haloalkyl, (C 2 -C 7) haloalkenyl, (C 2 -C 7) haloalkynyl, (Ci-C7) haloalkoxy (Ci-C7) alkyl, (C -C 7) alkoxy (Ci-C7) - haloalkyl, (CrC 7) haloalkoxy (Ci-C7) haloalkyl, (dC 7) alkylthio (Ci-C7) alkyl, (CrC 7 ) -haloalkylthio (C 1 -C 7 ) -alkyl,
R5 für Hydroxy, (Ci-C7)-Alkoxy, Aryloxy, (C3-C7)-Cycloalkyloxy, (C2-C7)-Alkenyloxy, (C2-C7)-Alkenyl-(Ci-C7)-alkyloxy, (Ci-C7)-Alkoxy-(Ci-C7)-alkyloxy, (C1-C7)- Alkylcarbonyloxy, Arylcarbonyloxy, Heteroarylcarbonyloxy, (C3-C7)- Cycloalkylcarbonyloxy, (Ci-C7)-Alkoxycarbonyloxy, (C2-C7)- Alkenyloxycarbonyloxy, Aryloxy-(d-C7)-alkyloxy, Aryl-(Ci-C7)-alkyloxy, (C1-C7)- Alkoxy-(Ci-C7)-alkoxy-(Ci-C7)-alkyloxy, (Ci-C7)-Alkylthio-(d-C7)-alkyloxy, Tris[(Ci-C7)-alkyl]silyloxy, (Ci-C7)-Alkyl-Bis[(CrC7)-alkyl]silyloxy, (d-C7)-Alkyl- bis(Aryl)silyloxy, Aryl-bis[(Ci-C7)— alkyljsilyloxy, Cycloalkyl-bis[(Ci-C7)- alkyl]silyloxy, Halo-bis[(Ci-C7)-alkyl]silyloxy, Tris[(Ci-C7)-alkyl]silyl-(Ci-C7)- alkoxy-(Ci-C7)-alkyloxy steht, R 5 is hydroxy, (Ci-C7) alkoxy, aryloxy, (C3-C7) cycloalkyloxy, (C 2 -C 7) alkenyloxy, (C 2 -C 7) alkenyl (Ci-C 7 ) -alkyloxy, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyloxy, (C 1 -C 7 ) -alkylcarbonyloxy, arylcarbonyloxy, heteroarylcarbonyloxy, (C 3 -C 7 ) -cycloalkylcarbonyloxy, (C 1 -C 7 ) -alkoxycarbonyloxy , (C2-C7) - Alkenyloxycarbonyloxy, aryloxy (dC 7) alkyloxy, aryl- (Ci-C7) alkyloxy, (C1-C7) - alkoxy (Ci-C7) alkoxy (Ci-C 7 ) -alkyloxy, (C 1 -C 7 ) -alkylthio (C 1 -C 7 ) -alkyloxy, tris [(C 1 -C 7 ) -alkyl] silyloxy, (C 1 -C 7 ) -alkyl bis [(C 1 -C 7 ) - alkyl] silyloxy, (dC 7 ) alkyl bis (aryl) silyloxy, aryl bis [(Ci-C 7 ) alkylsilyloxy, cycloalkyl bis [(Ci-C 7 ) alkyl] silyloxy, halo bis [( C 1 -C 7 ) -alkyl] silyloxy, tris [(C 1 -C 7 ) -alkyl] silyl- (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyloxy,
R6 für Nitro, Amino, Hydroxy, Hydrothio, Thiocyanato, Isothiocyanato, Halogen,R 6 for nitro, amino, hydroxy, hydrothio, thiocyanato, isothiocyanato, halogen,
(Ci-C7)-Alkyl, (C3-C7)-Cycloalkyl. (C2-C7)-Alkenyl, (C4-C7)-Cycloalkenyl, (C2-C7)- Alkinyl, Aryl-(C2-C7)-alkinyl, Tris[(Ci-C7)-alkyl]silyl-(C2-C7)-alkinyl, Aryl, Aryl- (Ci-C7)-alkyl, Aryl-(d-C7)-alkoxy, Heteroaryl, (Ci-C7)-Haloalkyl. (C3-C7)- Halocycloalkyl, (C2-C7)-Haloalkenyl. (Ci-C7)-Alkoxy, (d-C7)-Haloalkoxy,
Aryloxy, Heteroaryloxy, (C3-C7)-Cycloalkyloxy, (C3-C7)-Cycloalkyl-(Ci-C7)- alkoxy, (C2-C7)- (C2-C7)-Alkenyloxy, (C2-C7)-Alkinyl-(C2-C7)-alkyloxy, Hydroxy- (Ci-C7)-alkyl, (Ci-C7)-Alkoxy-(Ci-C7)-alkyl, Aryloxy-(CrC7)-alkyl, Heteroaryloxy- (Ci-C7)-alkyl, (Ci-C7)-Alkylthio, (Ci-C7)-Haloalkylthio, (Ci-C7)-Alkoxycarbonyl- (Ci-C7)-alkylthio, Arylthio, (C3-C7)-Cycloalkylthio, Heteroarylthio, (C1-C7)- Alkylthio-(Ci-C7)-alkyl, (Ci-C7)-Alkylamino, Bis[(Ci-C7)-alkyl]amino, (C2-C7)- Alkenylamino, (C3-C7)-Cycloalkylamino, (Ci-C7)-Alkylcarbonylamino, (C3-C7)- Cycloalkylcarbonylamino, Arylcarbonylamino, Heteroarylcarbonylamino, Formylamino, (Ci-C7)-Haloalkylcarbonylamino, (Ci-C7)-Alkoxycarbonylamino, (Ci-C7)-Alkylaminocarbonylamino, (Ci-C7)-Alkyl[(Ci-C7)- Alkyl]aminocarbonylamino, (Ci-C7)-Alkylsulfonylamino, (C3-C7)- Cycloalkylsulfonylamino, Arylsulfonylamino, Hetarylsulfonylamino, Sulfonyl- (Ci-C7)- aloalkylamino, Amino-(Ci-C7)-alkylsulfonyl, Amino-(Ci-C7)- haloalkylsulfonyl, (CrC7)-Alkylaminosulfonyl, Bis[(Ci-C7)-alkyl]aminosulfonyl, (C3-C7)-Cycloalkylaminosulfonyl, (Ci-C7)-Haloalkylaminosulfonyl, Aminosulfonyl, Heteroarylaminosulfonyl, Arylaminosulfonyl, Aryl-(Ci-C7)-alkylaminosulfonyl, (Ci-C7)-Alkylsulfonyl, (C3-C7)-Cycloalkylsulfonyl, Arylsulfonyl, (C1-C7)- Alkylsulfinyl, (C3-C7)-Cycloalkylsulfinyl, Arylsulfinyl, N.S-Bis[(Ci-C7)- alkyl]sulfonimidoyl, S-(Ci-C7)-Alkylsulfonimidoyl, (C1-C7)- Alkylsulfonylaminocarbonyl, (C3-C7)-Cycloalkylsulfonylaminocarbonyl, Aryl- (Ci-C7)-alkylcarbonylamino, (C3-C7)-Cycloalkyl-(Ci-C7)-alkylcarbonylamino, Heteroarylcarbonylamino, (Ci-C7)-Alkoxy-(Ci-C7)-alkylcarbonylamino, Hydroxy- (Ci-C7)-alkylcarbonylamino, (Ci-C7)-Alkoxycarbonylamino-(Ci-C7)- alkylcarbonylamino, Cyano, Cyano-(Ci-C7)-alkyl, Hydroxycarbonyl, (C1-C7)- Alkoxycarbonyl, (C3-C7)-Cycloalkoxycarbonyl, (C3-C7)-Cycloalkyl-(Ci-C7)- alkoxycarbonyl, Aryloxycarbonyl, Aryl-(CrC7)-alkoxycarbonyl, (C2-C7)- Alkenyloxycarbonyl, (C2-C7)-Alkinyloxycarbonyl, (Ci-C7)-Haloalkyloxycarbonyl, (Ci-C7)-Alkoxy-(Ci-C7)-alkoxycarbonyl, (C2-C7)-Alkenyloxy-(Ci-C7)- alkoxycarbonyl, (Ci-C7)-Alkylamino-(Ci-C7)-alkoxycarbonyl, Tris[(Ci-C7)- alkyl]silyloxy-(Ci-C7)-alkoxycarbonyl, Bis[(Ci-C7)-Alkyl]amino-(Ci-C7)- alkoxycarbonyl, (Ci-C7)-Alkyl[(Ci-C7)-alkyl]amino-(Ci-C7)-alkoxycarbonyl, Cyano-(Ci-C7)-alkoxycarbonyl, Heterocyclyl-N-(Ci-C7)-alkoxycarbonyl, (Ci-C7) alkyl, (C 3 -C 7) cycloalkyl. (C 2 -C 7 ) -alkenyl, (C 4 -C 7 ) -cycloalkenyl, (C 2 -C 7 ) -alkynyl, aryl- (C 2 -C 7 ) -alkynyl, tris [(C 1 -C 7 ) -alkyl ] silyl (C 2 -C 7) alkynyl, aryl, aryl (Ci-C7) alkyl, aryl (dC 7) alkoxy, heteroaryl, (Ci-C7) haloalkyl. (C 3 -C 7 ) -halocycloalkyl, (C 2 -C 7 ) -haloalkenyl. (C 1 -C 7 ) -alkoxy, (C 1 -C 4 ) -haloalkoxy, Aryloxy, heteroaryloxy, (C 3 -C 7 ) -cycloalkyloxy, (C 3 -C 7 ) -cycloalkyl- (C 1 -C 7 ) -alkoxy, (C 2 -C 7 ) - (C 2 -C 7 ) -alkenyloxy, (C 2 -C 7 ) - Alkynyl (C 2 -C 7 ) alkoxy, hydroxy (C 1 -C 7 ) alkyl, (C 1 -C 7 ) alkoxy (C 1 -C 7 ) alkyl, aryloxy (C 1 -C 7 ) alkyl, heteroaryloxy - (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkylthio, (C 1 -C 7 ) -haloalkylthio, (C 1 -C 7 ) -alkoxycarbonyl- (C 1 -C 7 ) -alkylthio, arylthio, (C 3 -C 7) cycloalkylthio, heteroarylthio, (C1-C7) - alkylthio (Ci-C7) alkyl, (Ci-C7) alkylamino, bis [(Ci-C 7) alkyl] amino, ( C 2 -C 7 ) - alkenylamino, (C 3 -C 7 ) -cycloalkylamino, (C 1 -C 7 ) -alkylcarbonylamino, (C 3 -C 7 ) -cycloalkylcarbonylamino, arylcarbonylamino, heteroarylcarbonylamino, formylamino, (C 1 -C 7 ) -haloalkylcarbonylamino, (Ci -C 7) alkoxycarbonylamino, (Ci-C 7) alkylaminocarbonylamino, (Ci-C 7) alkyl [(Ci-C7) - alkyl] aminocarbonylamino, (Ci-C 7) alkylsulfonylamino, (C3-C7) - Cycloalkylsulfonylamino, arylsulfonylamino, hetarylsulfonylamino, sulfonyl (Ci-C 7 ) - aloalkylamino, amino (Ci-C 7 ) -alkylsulfonyl, amine o- (C 1 -C 7 ) haloalkylsulfonyl, (C 1 -C 7 ) -alkylaminosulfonyl, bis [(C 1 -C 7 ) -alkyl] aminosulfonyl, (C 3 -C 7 ) -cycloalkylaminosulfonyl, (C 1 -C 7 ) -haloalkylaminosulfonyl, aminosulfonyl, heteroarylaminosulfonyl, arylaminosulfonyl, aryl- (Ci-C7) alkylaminosulfonyl, (Ci-C7) alkylsulphonyl, (C 3 -C 7) cycloalkylsulfonyl, arylsulfonyl, (C1-C7) - alkylsulfinyl, (C 3 -C 7) - cycloalkylsulfinyl, arylsulfinyl, NS-bis [(Ci-C7) - alkyl] sulfonimidoyl, S- (Ci-C7) -Alkylsulfonimidoyl, (C1-C7) - alkylsulfonylaminocarbonyl, (C3-C 7) -Cycloalkylsulfonylaminocarbonyl, aryl ( C 1 -C 7 -alkylcarbonylamino, (C 3 -C 7 ) -cycloalkyl- (C 1 -C 7 ) -alkylcarbonylamino, heteroarylcarbonylamino, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkylcarbonylamino, hydroxy- (Ci -C 7) alkylcarbonylamino, (Ci-C 7) alkoxycarbonylamino (Ci-C7) - alkylcarbonylamino, cyano, cyano (Ci-C 7) alkyl, hydroxycarbonyl, (C1-C7) - alkoxycarbonyl, (C3 -C 7) cycloalkoxycarbonyl, (C3-C7) -cycloalkyl- (Ci-C 7) - alkoxycarbonyl, aryloxycarbonyl, aryl (-C 7) -alkoxycarbonyl , (C 2 -C 7 ) -alkenyloxycarbonyl, (C 2 -C 7 ) -alkynyloxycarbonyl, (C 1 -C 7 ) -haloalkyloxycarbonyl, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkoxycarbonyl, (C 2 -C 7 ) alkenyloxy (Ci-C7) - alkoxycarbonyl, (Ci-C7) alkylamino- (Ci-C7) -alkoxycarbonyl, tris [(Ci-C7) - alkyl] silyloxy (C 7) - alkoxycarbonyl, bis [(C 1 -C 7 ) -alkyl] amino- (C 1 -C 7 ) -alkoxycarbonyl, (C 1 -C 7 ) -alkyl [(C 1 -C 7 ) -alkyl] amino- (C 1 -C 7 ) alkoxycarbonyl, cyano- (C 1 -C 7 ) -alkoxycarbonyl, heterocyclyl-N- (C 1 -C 7 ) -alkoxycarbonyl,
Heteroaryloxycarbonyl, Heteroaryl-(Ci-C7)-alkoxycarbonyl, Heterocyclyl-(Ci-C7)- alkoxycarbonyl, Heterocyclyloxycarbonyl, (C2-C7)-Alkenyl-(Ci-C7)-
alkoxycarbonyl, (C2-C7)-Alkinyl-(Ci-C7)-alkoxycarbonyl, Aryl-(C-2-C-7)- alkinyloxycarbonyl, Aryl-(C2-C7)-alkenyloxycarbonyl, Aminocarbonyl, (C1-C7)- Alkylaminocarbonyl, Bis[(Ci-C7)-alkyl]aminocarbonyl, (Ci-C7)-Alkyl[(Ci-C7)- Alkyljaminocarbonyl, (Ci-C7)-Alkyl[(CrC7)-Alkoxy]aminocarbonyl, (C2-C7)- Alkenylaminocarbonyl, (C3-C7)-Cycloalkylaminocarbonyl, Arylaminocarbonyl, Aryl-(Ci-C7)-alkylaminocarbonyl, Heteroaryl-(CrC7)-alkylaminocarbonyl, Cyano- (CrC7)-alkylaminocarbonyl, (Ci-C7)-Haloalkylaminocarbonyl, (C2-C7)-Alkinyl- (Ci-C7)-alkylaminocarbonyl, (Ci-C7)-Alkoxycarbonylaminocarbonyl, Aryl-(Ci-C7 - alkoxycarbonylaminocarbonyl, Hydroxycarbonyl-(Ci-C7)-alkyl, (C1-C7)- Alkoxycarbonyl-(Ci-C7)-alkyl, (C:3-C7)-Cycloalkoxycarbonyl-(Ci-C7)-alkyl, (C3-C7)-Cycloalkyl-(Ci-C7)-alkoxycarbonyl-(Ci-C7)-alkyl, (C2-C7)- Alkenyloxycarbonyl-(Ci-C7)-alkyl, Aryl-(Ci-C7)-alkoxycarbonyl-(Ci-C7)-alkyl, (Ci-C7)-Alkylaminocarbonyl-(CrC7)-alkyl, Aminocarbonyl-(Ci-C7)-alkyl, Heteroaryloxycarbonyl, heteroaryl- (C 1 -C 7 ) -alkoxycarbonyl, heterocyclyl- (C 1 -C 7 ) -alkoxycarbonyl, heterocyclyloxycarbonyl, (C 2 -C 7 ) -alkenyl- (C 1 -C 7 ) - alkoxycarbonyl, (C 2 -C 7) -alkynyl- (C 1 -C 7) -alkoxycarbonyl, aryl- (C-2-C-7) -alkynyloxycarbonyl, aryl- (C 2 -C 7) -alkenyloxycarbonyl, aminocarbonyl, (C 1 -C 7) - Alkylaminocarbonyl, bis [(Ci-C7) -alkyl] aminocarbonyl, (Ci-C7) -alkyl [(Ci-C7) - alkyljaminocarbonyl, (Ci-C7) -alkyl [(CrC7) -alkoxy] aminocarbonyl, (C2-C7 ) - alkenylaminocarbonyl, (C 3 -C 7) -cycloalkylaminocarbonyl, arylaminocarbonyl, aryl- (C 1 -C 7) -alkylaminocarbonyl, heteroaryl- (C 1 -C 7) -alkylaminocarbonyl, cyano- (C 1 -C 7) -alkylaminocarbonyl, (C 1 -C 7) -haloalkylaminocarbonyl, (C2 -C 7) alkynyl (C 1 -C 7) -alkylaminocarbonyl, (C 1 -C 7) -alkoxycarbonylaminocarbonyl, aryl- (C 1 -C 7 -alkoxycarbonylaminocarbonyl, hydroxycarbonyl- (C 1 -C 7) -alkyl, (C 1 -C 7) -alkoxycarbonyl- C 1 -C 7) -alkyl, (C 3 -C 7) -cycloalkoxycarbonyl- (C 1 -C 7) -alkyl, (C 3 -C 7 ) -cycloalkyl- (C 1 -C 7 ) -alkoxycarbonyl- (C 1 -C 7 ) -alkyl, (C 2 -C 7) -alkenyloxycarbonyl- (C 1 -C 7) -alkyl, aryl- (C 1 -C 7) -alkoxycarbonyl- (C 1 -C 7) -alkyl, (C 1 -C 7) -alkylaminocarbonyl- (C 1 -C 7) -alkyl, aminocarbonyl- (Ci-C7) alkyl,
Bis[(Ci-C7)-alkyl]aminocarbonyl-(CrC7)-alkyl, (C3-C7)-Cycloalkylaminocarbonyl- (Ci-C7)-alkyl, Aryl-(Ci-C7)-alkylaminocarbonyl-(Ci-C7)-alkyl, Heteroaryl-(Ci-C7)- alkylaminocarbonyl-(CrC7)-alkyl, Cyano-(Ci-C7)-alkylaminocarbonyl-(Ci-C7)- alkyl, (Ci-C7)-Haloalkylaminocarbonyl-(Ci-C7)-alkyl, (C2-C7)-Alkinyl-(Ci-C7)- alkylaminocarbonyl-(Ci-C7)-alkyl, (C3-C7)-Cycloalkyl-(Ci-C7)- alkylaminocarbonyi-(Ci-C7)-alkyl, (Ci-C7)-Alkoxycarbonylaminocarbonyl- (Ci-C7)-alkyl, Aryl-(Ci-C7)-alkoxycarbonylaminocarbonyl-(Ci-C7)-alkyl, (C1-C7)- Alkoxycarbonyl-(Ci-C7)-alkylaminocarbonyl, Hydroxycarbonyl-(CrC7)- alkylaminocarbonyl, Aryl-(Ci-C7)-alkoxycarbonyl-(Ci-C7)-alkylaminocarbonyl, (CrC7)-Alkoxycarbonyl-heterocyclyl-N-carbonyl, (Ci-C7)-Alkoxycarbonyl-(Cr CeJ-alkyl-heterocyclylidenaminocarbonyl, (C1-C7)- Alkoxycarbonylheterocyclyliden-(Ci-C6)-alkylaminocarbonyl (C1-C7)- Alkoxycarbonyl-(Ci-C7)-Alkyl((Ci-C7)-alkyl)aminocarbonyl, (C1-C7)- Alkoxycarbonyl-(C3-C7)-cycloalkylidenaminocarbonyl, Heterocyclyl-N-carbonyl, (Ci-C7)-Alkoxy-(Ci-C7)-alkylaminocarbonyi, Aminocarbonyl-(Ci-C7)- alkylaminocarbonyl, (Ci-C7)-Aikylaminocarbonyl-(Ci-C7)-alkylaminocarbonyl, (C3-C7)-Cycloalkylaminocarbonyl-(Ci-C7)-alkylaminocarbonyl, (C3-C7)- Cycloalkyl-(Ci-C7)-alkylaminocarbonyl, (C3-C7)-Cycloalkyl-(Ci-C7)- alkylaminocarbonyl-(Ci-C7)-alkyi, (C3-C7)-Cycloalkyl-(Ci-C7)- alkylaminocarbonyl-(Ci-C7)-alkylaminocarbonyl, (C2-C7)-Alkenyl-(d-C7)- alkylaminocarbonyl, (C2-C7)-Alkenylaminocarbonyl-(Ci-C7)-alkyl, (C2-C7)-
Alkenyl-(Ci-C7)-alkylaminocarbonyl-(Ci-C7)-alkyl, (Ci-C7)-Alkylcarbonyl, (C3-C7)- Cycloalkylcarbonyl, Arylcarbonyl, Formyi, Hydroxyiminomethyl, Bis [(Ci-C7) alkyl] aminocarbonyl (CRC7) alkyl, (C3-C7) -Cycloalkylaminocarbonyl- (Ci-C7) alkyl, aryl (Ci-C7) alkylaminocarbonyl (Ci-C 7 ) -alkyl, heteroaryl- (C 1 -C 7 ) -alkylaminocarbonyl- (C 1 -C 7 ) -alkyl, cyano- (C 1 -C 7 ) -alkylaminocarbonyl- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -haloalkylaminocarbonyl- (ci) C 7) alkyl, (C2-C7) alkynyl (Ci-C7) - alkylaminocarbonyl (Ci-C7) alkyl, (C3-C7) -cycloalkyl- (Ci-C 7) - alkylaminocarbonyi- (C 1 -C 7) -alkyl, (C 1 -C 7) -alkoxycarbonylaminocarbonyl- (C 1 -C 7) -alkyl, aryl- (C 1 -C 7) -alkoxycarbonylaminocarbonyl- (C 1 -C 7) -alkyl, (C 1 -C 7) -alkoxycarbonyl- (C 1 -C 7) -alkylaminocarbonyl, hydroxycarbonyl- (C 1 -C 7) -alkylaminocarbonyl, aryl- (C 1 -C 7) -alkoxycarbonyl- (C 1 -C 7) -alkylaminocarbonyl, (C 1 -C 7) -alkoxycarbonyl-heterocyclyl-N-carbonyl, (C 1 -C 7 ) -Alkoxycarbonyl- (C 1 -C 6 -alkyl-heterocyclylideno-aminocarbonyl, (C 1 -C 7) -alkoxycarbonyl-heterocyclylidene- (C 1 -C 6) -alkylaminocarbonyl (C 1 -C 7) -alkoxycarbonyl- (C 1 -C 7) -alkyl ((C 1 -C 7) -alkyl ) aminocarbonyl, (C 1 -C 7) -alkoxycarbonyl- (C 3 -C 7) -cycloalkylidene-aminocarbonyl, Hete rocyclyl-N-carbonyl, (C 1 -C 7) -alkoxy- (C 1 -C 7) -alkylaminocarbonyl, aminocarbonyl- (C 1 -C 7) -alkylaminocarbonyl, (C 1 -C 7) -alkylaminocarbonyl- (C 1 -C 7) -alkylaminocarbonyl, (C3 -C 7 ) -cycloalkylaminocarbonyl- (C 1 -C 7 ) -alkylaminocarbonyl, (C 3 -C 7 ) -cycloalkyl- (C 1 -C 7 ) -alkylaminocarbonyl, (C 3 -C 7 ) -cycloalkyl- (C 1 -C 7 ) -alkylaminocarbonyl- C 1 -C 7 ) -alkyi, (C 3 -C 7 ) -cycloalkyl- (C 1 -C 7 ) -alkylaminocarbonyl- (C 1 -C 7 ) -alkylaminocarbonyl, (C 2 -C 7 ) -alkenyl- (C 1 -C 7 ) -alkylaminocarbonyl, (C 2 -C 7) -alkenylaminocarbonyl- (C 1 -C 7) -alkyl, (C 2 -C 7) - Alkenyl- (C 1 -C 7 ) -alkylaminocarbonyl- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkylcarbonyl, (C 3 -C 7 ) -cycloalkylcarbonyl, arylcarbonyl, formyl, hydroxyiminomethyl,
Aminoiminomethyl, (Ci-C7)-Alkoxyiminomethyl, (Ci-C7)-AlkylaminoiminomethyL Bis[(Ci-C7)-alkyl]aminoiminomethyl, (C3-C7)-Cycloalkoxyiminomethyl, (C3-C7)- Cycloalkyl-(Ci-C7)-alkoximinomethyl, Aryloximinomethyl, Aryl-(d-C7)- alkoxyiminomethyl, Aryl-(Ci-C7)-alkylaminoiminomethyl, (C2-C7)- Alkenyloxyiminomethyl, Arylaminoiminomethyl, Arylsulfonylaminoiminomethyl, Heteroaryl-(d-C7)-alkyl, Heterocyclyl-(Ci-C7)-alkyl, Aminoiminomethyl, (C 1 -C 7 ) -alkoxyiminomethyl, (C 1 -C 7 ) -alkylaminoiminomethyl, bis [(C 1 -C 7 ) -alkyl] aminoiminomethyl, (C 3 -C 7 ) -cycloalkoxyiminomethyl, (C 3 -C 7 ) -cycloalkyl- ( Ci-C 7) -alkoximinomethyl, Aryloximinomethyl, aryl (dC 7) - alkoxyiminomethyl, aryl (Ci-C 7) -alkylaminoiminomethyl, (C2-C7) - Alkenyloxyiminomethyl, Arylaminoiminomethyl, Arylsulfonylaminoiminomethyl, heteroaryl (dC 7) alkyl , Heterocyclyl (C 1 -C 7 ) -alkyl,
Hydroxycarbonylheterocyclyl, (Ci-C7)-Alkoxycarbonylheterocyclyl, (C2-C7)- Alkenyloxycarbonylheterocyclyl, (C2-C7)-Alkenyl-(Ci-C7)- alkoxycarbonylheterocyclyl, Aryl-(Ci-C7)-alkoxycarbonylheterocyclyl, (C3-C7)- Cycloalkoxycarbonylheterocyclyl, (C3-C7)-Cycloalkyl-(CrC7)- alkoxycarbonylheterocyclyl, Aminocarbonylheterocyclyl, (C1-C7)- Alkylaminocarbonylheterocyclyl, Bis[(Ci-C7)-Alkyl]aminocarbonylheterocyclyl, (C3-C7)-Cycloalkylaminocarbonylheterocyclyl, Aryl-(Ci-C7)- alkylaminocarbonylheterocyclyl, (C2-C7)-Alkenylaminocarbonylheterocyclyl, Hydroxycarbonylheterocyclyl-(Ci-C7)-alkyl, (CrC7)-Alkoxycarbonylheterocyclyl- (Ci-C7)-alkyl, Hydroxycarbonyl-(C3-C7)-cycloalkyl-(Ci-C7)-alkyL (C1-C7)- Alkoxycarbonyl-(C3-C7)-cycloalkyl-(Ci-C7)-alkyl, Hydroxyaminocarbonyl, Hydroxycarbonylheterocyclyl, (Ci-C 7) -Alkoxycarbonylheterocyclyl, (C2-C7) - Alkenyloxycarbonylheterocyclyl, (C2-C7) alkenyl (Ci-C7) - alkoxycarbonylheterocyclyl, aryl (Ci-C 7) -alkoxycarbonylheterocyclyl, (C3 C7) - Cycloalkoxycarbonylheterocyclyl, (C3-C7) cycloalkyl (CrC 7) - alkoxycarbonylheterocyclyl, Aminocarbonylheterocyclyl, (C1-C7) - Alkylaminocarbonylheterocyclyl, bis [(Ci-C 7) alkyl] aminocarbonylheterocyclyl, (C3-C 7 ) -Cycloalkylaminocarbonylheterocyclyl, aryl- (C 1 -C 7 ) -alkylaminocarbonyl-heterocyclyl, (C 2 -C 7 ) -alkenylaminocarbonyl-heterocyclyl, hydroxycarbonyl-heterocyclyl- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkoxycarbonyl-heterocyclyl- (C 1 -C 7 ) -alkyl , hydroxycarbonyl (C 3 -C 7) cycloalkyl- (Ci-C7) alkyl (C1-C7) - alkoxycarbonyl (C3-C7) cycloalkyl- (Ci-C7) alkyl, hydroxyaminocarbonyl,
(Ci-C7)-Alkoxyaminocarbonyl, Aryl-(Ci-C7)-alkoxyaminocarbonyl, Heterocyclyl, (d-C7)-Alkylcarbonyloxy, Arylcarbonyloxy, Heteroarylcarbonyloxy, (C3-C7)- Cycloalkylcarbonyloxy, (Ci-C7)-Alkoxycarbonyloxy, (C2-C7)- Alkenyloxycarbonyloxy steht, (C 1 -C 7 ) -alkoxyaminocarbonyl, aryl- (C 1 -C 7 ) -alkoxyaminocarbonyl, heterocyclyl, (C 1 -C 7 ) -alkylcarbonyloxy, arylcarbonyloxy, heteroarylcarbonyloxy, (C 3 -C 7 ) -cycloalkylcarbonyloxy, (C 1 -C 7 ) -alkoxycarbonyloxy, (C2-C7) - alkenyloxycarbonyloxy,
R7, R8 , R9 und R10 unabhängig voneinander für Wasserstoff, Halogen, Nitro, Amino, Cyano, (d-C7)-Alkyl, Aryl, Heteroaryl, (C3-C7)-Cycloalkyi, (C4-C7)-Cycloalkenyl, (C2-C7)-Alkenyl, (C2-C7)-Alkinyi, (C2-C7)-Alkenyl-(Ci-C7)-alkyl, (C2-C7)-Alkinyl- (Ci-C7)-aikyl, Hydroxy, (Ci-C7)-Alkoxy, (Ci-C7)-Alkoxy-(Ci-C7)-alkoxy, (C1-C7)- Aikoxy-(Ci-C7)-alkyl, Hydroxy-(Ci-C7)-alkyl, (Ci-C7)-Haioaikoxy, (C1-C7)- Haloalkyi, (C2-C7)-Haloalkenyl, (C2-C7)-Haloalkinyl, (Ci-C7)-Haloalkoxy-(Ci-C7)- alkyl, (Ci-C7)-Alkoxy-(Ci-C7)-haloalkyl, (Ci-C7)-Haloalkoxy-(Ci-C7)-haloalkyl, Hydrothio, (Ci-C7)-Alkylthio, (CrC7)-Haloalkylthio, (Ci-C7)-Alkylthio-(Ci-C7)- alkyl, (Ci-C7)-Haloalkylthio-(Ci-C7)-alkyl, (Ci-C7)-Alkylamino, Bis[(Ci-C7)- alkyl]amino, (C2-C7)-Alkenylamino, (C3-C7)-Cycloalkylamino, (C1-C7)-
Alkylcarbonylamino, (C3-C7)-Cycloalkylcarbonylamino, Arylcarbonylamino, Heteroarylcarbonylamino, Formylamino, (CrC7)-Haloalkylcarbonyiamino, (Ci-C7)-Alkoxycarbonylamino, (Ci-C7)-Alkylaminocarbonylamino, (C1-C7)- Aikyl[(Ci-C7)-Alkyl]aminocarbonylamino, (Ci-C7)-Alkylsulfonylamino, (C3-C7)- Cycloalkylsulfonylamino, Arylsulfonylamino, Hetarylsulfonylamino, Sulfonyl- (Ci-C7)-haloalkylamino, Amino-(Ci-C7)-alkylsulfonyl, Amino-(CrC7)- haloalkylsulfonyl, (Ci-C7)-Alkylaminosulfonyl, Bis[(Ci-C7)-alkyl]aminosulfonyl, (C3-C7)-Cycloalkylaminosulfonyl, (Ci-C7)-Haloalkylaminosulfonyl, R 7, R 8, R 9 and R 10 are independently hydrogen, halogen, nitro, amino, cyano, (dC 7) alkyl, aryl, heteroaryl, (C 3 -C 7) -Cycloalkyi, (C 4 -C 7) cycloalkenyl, (C2-C7) alkenyl, (C2-C7) -Alkinyi, (C2-C7) alkenyl (Ci-C7) alkyl, (C 2 -C 7) alkynyl (Ci-C7) -alkyl, hydroxy, (Ci-C7) alkoxy, (Ci-C7) alkoxy (Ci-C7) alkoxy, (C1-C7) - Aikoxy- (Ci-C 7 ) alkyl, hydroxy (Ci-C7) alkyl, (Ci-C 7) -Haioaikoxy, (C1-C7) - Haloalkyi, (C 2 -C 7) haloalkenyl, (C2-C7) haloalkynyl , (Ci-C7) haloalkoxy (Ci-C7) - alkyl, (Ci-C7) alkoxy (Ci-C7) haloalkyl, (Ci-C7) haloalkoxy (Ci-C 7 ) haloalkyl, Hydrothio, (Ci-C7) alkylthio, (CrC 7) haloalkylthio, (Ci-C7) -alkylthio (Ci-C 7) - alkyl, (Ci-C 7) -Haloalkylthio- ( C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkylamino, bis [(C 1 -C 7 ) -alkyl] -amino, (C 2 -C 7 ) -alkenylamino, (C 3 -C 7 ) -cycloalkylamino, (C 1 -C 7 ) - Alkylcarbonylamino, (C 3 -C 7) -cycloalkylcarbonylamino, arylcarbonylamino, heteroarylcarbonylamino, formylamino, (C 1 -C 7) -haloalkylcarbonyiamino, (C 1 -C 7) -alkoxycarbonylamino, (C 1 -C 7) -alkylaminocarbonylamino, (C 1 -C 7) -alkyl [(C 1 -C 7) ) -Alkyl] aminocarbonylamino, (C 1 -C 7) -alkylsulfonylamino, (C 3 -C 7) -cycloalkylsulfonylamino, arylsulfonylamino, hetarylsulfonylamino, sulfonyl- (C 1 -C 7) -haloalkylamino, amino- (C 1 -C 7) -alkylsulfonyl, amino- (C 1 -C 7 ) haloalkylsulfonyl, (C 1 -C 7) -alkylaminosulfonyl, bis [(C 1 -C 7) -alkyl] aminosulfonyl, (C 3 -C 7) -cycloalkylaminosulfonyl, (C 1 -C 7) -haloalkylaminosulfonyl,
Heteroarylaminosulfonyl, Arylaminosulfonyl, Aryl-(Ci-C7)-alkylaminosulfonyl, (Ci-C7)-Alkylsulfonyl, (C3-C7)-Cycloalkylsulfonyl, Arylsulfonyl, Hydroxycarbonyi, (CrC7)-Alkoxycarbonyl, (C3-C7)-Cycloalkoxycarbonyl, (C3-C7)-Cycloalkyl- (d-C7)-alkoxycarbonyl, Aryloxycarbonyl, Aryl-(Ci-C7)-alkoxycarbonyl, (C2-C7)- Alkenyloxycarbonyl, (C2-C7)-Alkinyloxycarbonyl, Aminocarbonyl, (C1-C7)- Alkylaminocarbonyl, Bis[(Ci-C7)-alkyl]aminocarbonyl, (Ci-C7)-Alkyl[(d-C7)- Alkyljaminocarbonyl, (Ci-C7)-Alkyl[(CrC7)-Alkoxy]aminocarbonyl, (C2-C7)- Alkenylaminocarbonyl, (C3-C7)-Cycloalkylaminocarbonyl, Arylaminocarbonyl, Aryl-(Ci-C7)-alkylaminocarbonyl stehen, Heteroarylaminosulfonyl, arylaminosulfonyl, aryl- (C 1 -C 7) -alkylaminosulfonyl, (C 1 -C 7) -alkylsulfonyl, (C 3 -C 7) -cycloalkylsulfonyl, arylsulfonyl, hydroxycarbonyi, (C 1 -C 7) -alkoxycarbonyl, (C 3 -C 7) -cycloalkoxycarbonyl, (C3 -C 7) -cycloalkyl- (C 1 -C 7) -alkoxycarbonyl, aryloxycarbonyl, aryl- (C 1 -C 7) -alkoxycarbonyl, (C 2 -C 7) -alkenyloxycarbonyl, (C 2 -C 7) -alkynyloxycarbonyl, aminocarbonyl, (C 1 -C 7) - Alkylaminocarbonyl, bis [(Ci-C7) -alkyl] aminocarbonyl, (Ci-C7) -alkyl [(d-C7) -alkyljaminocarbonyl, (Ci-C7) -alkyl [(CrC7) -alkoxy] aminocarbonyl, (C2-C7 ) - alkenylaminocarbonyl, (C 3 -C 7) -cycloalkylaminocarbonyl, arylaminocarbonyl, aryl- (C 1 -C 7) -alkylaminocarbonyl,
A1 , A2, A3 und A4 gleich oder verschieden sind und unabhängig voneinander für NA 1 , A 2 , A 3 and A 4 are the same or different and are independently N
(Stickstoff) oder die Gruppierungen C-H, C-CH3, C-F, C-Cl, C-Br, C-l, C-OCF3, C-OCH3, C-CF3, C-CO2H, C-CO2CH3 stehen, wobei jedoch in keinem Fall mehr als zwei N-Atome benachbart sind, (Nitrogen) or the groupings CH, C-CH3, CF, C-Cl, are C-Br Cl, C-OCF3, C-OCH3, C-CF 3, C-CO2H, C-CO2CH3, but in no Case more than two N atoms are adjacent,
R1 und R12 unabhängig voneinander für Wasserstoff, Halogen, (Ci-C7)-Alkyl, Aryl, Heteroaryl, Heterocyclyl, (C3-C7)-Cycloalkyl, (C2-C7)-Alkenyl, (C2-C7)-Alkinyl, (Ci-C7)-Alkoxy, (Ci-C7)-Alkoxy-(Ci-C7)-alkyl, Aryloxy-(Ci-C7)-alkyl, (C1-C7)- Haloalkoxy, (Ci-C7)-Haloalkyl, (Ci-C7)-Haloalkoxy-(Ci-C7)-alkyl, (Ci-C7)-Alkoxy- (Ci-C7)-haloalkyl, (Ci-C7)-Haloalkoxy-(Ci-C7)-haloalkyl, (Ci-C7)-Alkylthio, (Ci-C7)-Haloalkylthio, (Ci-C7)-Alkylthio-(Ci-C7)-alkyl, Hydroxycarbonyi, (C1-C7)- Alkoxycarbonyl, (C3-C7)-Cycloalkoxycarbonyl, (C3-C7)-Cycloalkyl-(Ci-C7)- alkoxycarbonyl, Aryloxycarbonyl, Aryl-(d-C7)-alkoxycarbonyl, (C2-C7)- Alkenyloxycarbonyl, (C2-C-7)-Alkinyloxycarbonyl, Aminocarbonyl, (C1-C7)- Alkylaminocarbonyl, Bis[(CrC7)-alkyl]aminocarbonyl, (Ci-C7)-Alkyl[(d-C7)- Alkyl]aminocarbonyl, (CrC7)-Alkyl[(Ci-C7)-Alkoxy]aminocarbonyl, (C2-C7)-
Alkenylaminocarbonyl, (C3-C7)-Cycloalkylaminocarbonyl, Arylaminocarbonyl, Aryl-(Ci-C7)-alkylaminocarbonyl stehen, R 1 and R 12 independently of one another represent hydrogen, halogen, (C 1 -C 7 ) -alkyl, aryl, heteroaryl, heterocyclyl, (C 3 -C 7 ) -cycloalkyl, (C 2 -C 7 ) -alkenyl, (C 2 - C 7 ) -alkynyl, (C 1 -C 7 ) -alkoxy, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, aryloxy- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) - Haloalkoxy, (Ci-C 7 ) -haloalkyl, (Ci-C 7 ) -haloalkoxy- (Ci-C7) -alkyl, (Ci-C 7 ) -alkoxy- (Ci-C 7 ) -haloalkyl, (Ci-C7 Haloalkoxy- (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -alkylthio, (C 1 -C 7 ) -haloalkylthio, (C 1 -C 7 ) -alkylthio (C 1 -C 7 ) -alkyl, hydroxycarbonyi, (C1-C7) - alkoxycarbonyl, (C3-C7) -cycloalkoxycarbonyl, (C3-C7) -cycloalkyl- (Ci-C7) -alkoxycarbonyl, aryloxycarbonyl, aryl- (d-C7) -alkoxycarbonyl, (C2-C7) - Alkenyloxycarbonyl, (C 2 -C 7) -alkynyloxycarbonyl, aminocarbonyl, (C 1 -C 7) -alkylaminocarbonyl, bis [(C 1 -C 7) -alkyl] -aminocarbonyl, (C 1 -C 7) -alkyl [(C 1 -C 7) -alkyl] -aminocarbonyl, (C 1 -C 7) -alkyl [(C 1 -C 7) -alkoxy] aminocarbonyl, (C 2 -C 7) - Alkenylaminocarbonyl, (C 3 -C 7) -cycloalkylaminocarbonyl, arylaminocarbonyl, aryl- (C 1 -C 7) -alkylaminocarbonyl,
A5 für S (Schwefel), O (Sauerstoff) oder die Gruppierungen N-H, N-CH3, N-CH2CH3, N- CH(CH3)2, N-C02t-Bu, N-Aryl, N-Heteroaryl, N-Heterocyclyl steht, A 5 for S (sulfur), O (oxygen) or the groupings NH, N-CH 3 , N-CH 2 CH 3 , N-CH (CH 3 ) 2 , N-CO 2 t-Bu, N-aryl, N-heteroaryl , N-heterocyclyl,
R13, R14, R17 und R18 unabhängig voneinander für Wasserstoff, (Ci-C-7)-Alkyl, Halogen, (C3-C7)-Cycloalkyl, Aryl, Heteroaryl, Heterocyclyl, (C2-C7)-Alkenyl, (C2-C7)- Alkenyl-(Ci-C7)-alkyl, Aryl-(Ci-C7)-alkyl, (Ci-C7)-Alkoxy, (Ci-C7)-Alkoxy-(Ci-C7)- alkoxy, (Ci-C7)-Alkoxy-(Ci-C7)-alkyl, Hydroxy, (Ci-C7)-Haloalkyl, (C1-C7)- Haloalkylthio stehen oder R 13, R 14, R 17 and R 18 are independently hydrogen, (Ci-C-7) alkyl, halogen, (C3-C 7) cycloalkyl, aryl, heteroaryl, heterocyclyl, (C 2 -C 7) Alkenyl, (C 2 -C 7 ) -alkenyl- (C 1 -C 7 ) -alkyl, aryl- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkoxy, (C 1 -C 7 ) -alkoxy- ( Ci-C 7 ) - alkoxy, (Ci-C7) -alkoxy- (Ci-C 7 ) -alkyl, hydroxy, (Ci-C 7 ) -haloalkyl, (C 1 -C 7 ) - haloalkylthio or
R13 und R17 mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls weiter substituierten 5 bis 7-gliedrigen Ring bilden, R 13 and R 17 with the atoms to which they are attached form a completely saturated or partially saturated, optionally further substituted 5 to 7-membered ring,
A6, A7 gleich oder verschieden sind und unabhängig voneinander für O (Sauerstoff), S (Schwefel), N-H, N-OCH3, N-CH3 oder die Gruppierung CR15R16 stehen, wobei jedoch in keinem Fall zwei N-, O- oder S-Atome benachbart sind, und wobei R15 und R16 in der Gruppierung CR15R16 jeweils gleiche oder verschiedene A 6 , A 7 are the same or different and independently of one another are O (oxygen), S (sulfur), NH, N-OCH 3, N-CH 3 or the group CR 15 R 16 , although in each case two N-, O or S atoms are adjacent, and wherein R 15 and R 16 in the group CR 15 R 16 are identical or different
Bedeutungen gemäß der nachstehenden Definition haben und Have meanings as defined below and
R15 und R16 unabhängig voneinander für Wasserstoff, Halogen, (d-C7)-Alkyl, Aryl, Heteroaryl, Heterocyclyl, (C3-C7)-Cycloalkyl, (C2-C7)-Alkenyl, (CrC7)-Alkoxy, (Ci-C7)-Alkoxy-(Ci-C7)-alkyl, Aryloxy-(CrC7)-alkyl, (Ci-C7)-Haloalkoxy, (C1-C7)- Haloalkyl, (Ci-C7)-Haloalkoxy(Ci-C7)-alkyl, (Ci-C7)-Alkoxy-(Ci-C7)-haloalkyl, (Ci-C7)-Haloalkoxy-(Ci-C7)-haloalkyl, (Ci-C7)-Alkylthio, (Ci-C7)-Haloalkylthio, (Ci-C7)-Alkylthio-(Ci-C7)-alkyl, Hydroxycarbonyl, (Ci-C7)-Alkoxycarbonyl, (C3-C7)-Cycloalkoxycarbonyl, (C3-C7)-Cycloalkyl-(Ci-C7)-alkoxycarbonyl, Aryloxycarbonyl, Aryl-(d-C7)-alkoxycarbonyl, (C2-C7)-Alkenyloxycarbonyl, R 15 and R 16 independently of one another represent hydrogen, halogen, (C 1 -C 7 ) -alkyl, aryl, heteroaryl, heterocyclyl, (C 3 -C 7 ) -cycloalkyl, (C 2 -C 7 ) -alkenyl, (CrC 7 ) Alkoxy, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, aryloxy- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -haloalkoxy, (C 1 -C 7 ) -haloalkyl, C 7 ) -haloalkoxy (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -haloalkoxy- (C 1 -C 7 ) -haloalkyl, ( C 1 -C 7 ) -alkylthio, (C 1 -C 7 ) -haloalkylthio, (C 1 -C 7 ) -alkylthio (C 1 -C 7 ) -alkyl, hydroxycarbonyl, (C 1 -C 7 ) -alkoxycarbonyl, (C 3 -C 7 ) -cycloalkoxycarbonyl , (C 3 -C 7) -cycloalkyl- (C 1 -C 7) -alkoxycarbonyl, aryloxycarbonyl, aryl- (C 1 -C 7) -alkoxycarbonyl, (C 2 -C 7) -alkenyloxycarbonyl,
(C2-C7)-Alkinyloxycarbonyl, Aminocarbonyl, (Ci-C7)-Alkylaminocarbonyl, Bis[(Ci-C7)-alkyl]aminocarbonyl, (Ci-C7)-Alkyl[(CrC7)-Alkyl]aminocarbonyl, (CrC7)-Alkyl[(Ci-C7)-Alkoxy]aminocarbonyl, (C2-C7)-Alkenylaminocarbonyl, (C3-C7)-Cycloalkylaminocarbonyl, Arylaminocarbonyl, Aryl-(d-C7)-
alkylaminocarbonyl, Amino, (Ci-C7)-Alkylamino, (C3-C7)-Cycloalkylamino, Bis- [(Ci-C7)-Alkyl]amino stehen, (C 2 -C 7) -alkynyloxycarbonyl, aminocarbonyl, (C 1 -C 7) -alkylaminocarbonyl, bis [(C 1 -C 7) -alkyl] aminocarbonyl, (C 1 -C 7) -alkyl [(C 1 -C 7) -alkyl] aminocarbonyl, (C 1 -C 7) Alkyl [(C 1 -C 7) alkoxy] aminocarbonyl, (C 2 -C 7) alkenylaminocarbonyl, (C 3 -C 7) -cycloalkylaminocarbonyl, arylaminocarbonyl, aryl- (dC-C) - alkylaminocarbonyl, amino, (C 1 -C 7) -alkylamino, (C 3 -C 7) -cycloalkylamino, bis- [(C 1 -C 7) -alkyl] -amino,
R19, R20, R22 und R23 unabhängig voneinander für Wasserstoff, (Ci-C7)-Alkyl, Halogen, (C3-C7)-Cycloalkyl, Aryl, Heteroaryl, Heterocyclyl, (C2-C7)-Alkenyl, Aryl-(Ci-C7)- alkyl, (Ci-C7)-Alkoxy, (Ci-C7)-Alkoxy-(Ci-C7)-alkoxy, (Ci-C7)-Alkoxy-(Ci-C7)- alkyl, (Ci-C7)-Haloalkyl stehen, R 19 , R 20 , R 22 and R 23 independently of one another represent hydrogen, (C 1 -C 7 ) -alkyl, halogen, (C 3 -C 7 ) -cycloalkyl, aryl, heteroaryl, heterocyclyl, (C 2 -C 7 ) - alkenyl, aryl (Ci-C7) - alkyl, (Ci-C7) alkoxy, (Ci-C7) alkoxy (Ci-C7) alkoxy, (Ci-C7) alkoxy ( Ci-C 7 ) - alkyl, (Ci-C 7 ) -haloalkyl,
A8 für O (Sauerstoff), S (Schwefel), N-H, N-CH3, N-OCH3 oder die Gruppierung CHR21 steht und wobei R21 in der Gruppierung CHR21 die Bedeutung gemäß der nachstehenden Definition hat, A 8 is O (oxygen), S (sulfur), NH, N-CH 3 , N-OCH 3 or the moiety CHR 21 , and wherein R 21 in the moiety CHR 21 has the meaning as defined below,
R21 für Wasserstoff, Halogen, (Ci-C7)-Alkyl, Aryl, Heteroaryl, Heterocyclyl, (C3-C7)- Cycloalkyl, (C2-C7)-Alkenyl, (CrC7)-Alkoxy, (Ci-C7)-Alkoxy-(Ci-C7)-alkyl, Aryloxy-(Ci-C7)-alkyl, (Ci-C7)-Haloalkoxy, (Ci-C7)-Haloalkyl, (CrC7)-Alkoxy- (Ci-C7)-haloalkyl, (Ci-C7)-Haloalkoxy-(Ci-C7)-haloalkyl, (Ci-C7)-Alkylthio, R 21 is hydrogen, halogen, (C 1 -C 7 ) -alkyl, aryl, heteroaryl, heterocyclyl, (C 3 -C 7 ) -cycloalkyl, (C 2 -C 7 ) -alkenyl, (C 1 -C 7 ) -alkoxy, (Ci-C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, aryloxy- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -haloalkoxy, (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -alkoxy (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -haloalkoxy- (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -alkylthio,
(CrC7)-Haloalkylthio, (Ci-C7)-Alkylthio-(Ci-C7)-alkyl, Hydroxycarbonyl, (C1-C7)- Alkoxycarbonyl, (C3-C7)-Cycloalkoxycarbonyl, Aryl-(Ci-C7)-alkoxycarbonyl, (C2-C7)-Alkenyloxycarbonyl, (C2-C7)-Alkinyloxycarbonyl, Aminocarbonyl, (C 1 -C 7 ) -haloalkylthio, (C 1 -C 7 ) -alkylthio (C 1 -C 7 ) -alkyl, hydroxycarbonyl, (C 1 -C 7 ) -alkoxycarbonyl, (C 3 -C 7 ) -cycloalkoxycarbonyl, aryl- (C 1 -C 7 ) alkoxycarbonyl, (C 2 -C 7) -alkenyloxycarbonyl, (C 2 -C 7) -alkynyloxycarbonyl, aminocarbonyl,
(Ci-C7)-Alkylaminocarbonyl, Bis[(Ci-C7)-alkyl]aminocarbonyl, (C1-C7)- Alkyl[(CrC7)-Alkyl]aminocarbonyl, (CrC7)-Alkyl[(Ci-C7)-Alkoxy]aminocarbonyl, (C2-C7)-Alkenylaminocarbonyl, (C3-C7)-Cycloalkylaminocarbonyl, (C 1 -C 7) -alkylaminocarbonyl, bis [(C 1 -C 7) -alkyl] aminocarbonyl, (C 1 -C 7) -alkyl [(C 1 -C 7) -alkyl] aminocarbonyl, (C 1 -C 7) -alkyl [(C 1 -C 7) -alkoxy] aminocarbonyl, (C 2 -C 7) -alkenylaminocarbonyl, (C 3 -C 7) -cycloalkylaminocarbonyl,
Arylaminocarbonyl, Aryl-(Ci-C-7)-alkylaminocarbonyl, Amino, (d-C7)-Alkylamino, (C3-C7)-Cycloalkylamino, Bis[(Ci-C7)-Alkyl]amino steht, Arylaminocarbonyl, aryl- (C 1 -C 7) -alkylaminocarbonyl, amino, (C 1 -C 7) -alkylamino, (C 3 -C 7) -cycloalkylamino, bis [(C 1 -C 7) -alkyl] -amino,
R24, R25, R26, R28, R29 und R30 unabhängig voneinander für Wasserstoff, (Ci-C7)-Alkyl, Halogen, (C3-C7)-Cycloalkyl, Aryl, Heteroaryl, Heterocyclyl, (C2-C7)-Alkenyl, (Ci-C7)-Alkoxy, (Ci-C7)-Alkoxy-(Ci-C7)-alkoxy, (Ci-C7)-Alkoxy-(Ci-C7)-alkyl, (Ci-C7)-Haloalkyl, (Ci-C7)-Alkylthio, (Ci-C7)-Haloalkylthio stehen, R 24 , R 25 , R 26 , R 28 , R 29 and R 30 independently of one another represent hydrogen, (C 1 -C 7 ) -alkyl, halogen, (C 3 -C 7 ) -cycloalkyl, aryl, heteroaryl, heterocyclyl, (C 2 -C 4 ) -cycloalkyl, C7) alkenyl, (C 1 -C 7 ) -alkoxy, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkoxy, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, (Ci -C 7) haloalkyl, (Ci-C7) -alkylthio, (Ci-C 7) are haloalkylthio,
A9 für O (Sauerstoff), S (Schwefel), N-H, N-CH3, N-OCH3 oder die Gruppierung CHR27 steht und wobei R27 in der Gruppierung CHR27 die Bedeutung gemäß der nachstehenden Definition hat und
R27 für Wasserstoff, Halogen, (Ci-C-7)-Alkyl, Aryl, Heteroaryl, Heterocyclyl, (C3-C7)- Cycloalkyl, (C2-C7)-Alkenyl, (Ci-C7)-Alkoxy, (Ci-C7)-Alkoxy-(Ci-C7)-alkyl, Aryloxy-(Ci-C7)-alkyl, (Ci-C7)-Haloalkoxy, (Ci-C7)-Haloalkyl, (CrC7)-Alkylthio, (d-C7)-Haloalkylthio, Hydroxycarbonyl, (CrC7)-Alkoxycarbonyl, (C3-C7)- Cycloalkoxycarbonyl, Aryl-(d-C7)-alkoxycarbonyl, (C2-C7)-Alkenyloxycarbonyl, (C2-C7)-Alkinyloxycarbonyl, Aminocarbonyl, (Ci-C7)-Alkylaminocarbonyl, Bis[(Ci-C7)-alkyl]aminocarbonyl, (Ci-C7)-Alkyl[(CrC7)-Alkyl]aminocarbonyl, (Ci-C7)-Alkyl[(Ci-C7)-Alkoxy]aminocarbonyl, (C2-C7)-Alkenylaminocarbonyl, (C3-C7)-Cycloalkylaminocarbonyl, Arylaminocarbonyl, Aryl-(Ci-C7)- alkylaminocarbonyl, Amino, (Ci-C7)-Alkylamino, (C3-C7)-Cycloalkylamino, Bis[(Ci-C7)-Alkyl]amino steht. A 9 is O (oxygen), S (sulfur), NH, N-CH 3 , N -OCH 3 or the moiety CHR 27 and wherein R 27 in the moiety CHR 27 has the meaning as defined below and R 27 represents hydrogen, halogen, (C 1 -C 7 ) -alkyl, aryl, heteroaryl, heterocyclyl, (C 3 -C 7 ) -cycloalkyl, (C 2 -C 7 ) -alkenyl, (C 1 -C 7 ) -alkoxy, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, aryloxy- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -haloalkoxy, (C 1 -C 7 ) -haloalkyl, (C rC 7 ) -Alkylthio, (C 1 -C 7) -haloalkylthio, hydroxycarbonyl, (C 1 -C 7) -alkoxycarbonyl, (C 3 -C 7) -cycloalkoxycarbonyl, aryl- (C 1 -C 7) -alkoxycarbonyl, (C 2 -C 7) -alkenyloxycarbonyl, (C 2 -C 7) ) -Alkynyloxycarbonyl, aminocarbonyl, (C 1 -C 7) -alkylaminocarbonyl, bis [(C 1 -C 7) -alkyl] aminocarbonyl, (C 1 -C 7) -alkyl [(C 1 -C 7) -alkyl] aminocarbonyl, (C 1 -C 7) -alkyl [ (C 1 -C 7) -alkoxy] aminocarbonyl, (C 2 -C 7) -alkenylaminocarbonyl, (C 3 -C 7) -cycloalkylaminocarbonyl, arylaminocarbonyl, aryl- (C 1 -C 7) -alkylaminocarbonyl, amino, (C 1 -C 7) -alkylamino, (C3 -C7) cycloalkylamino, bis [(C 1 -C 7 ) alkyl] amino.
Ganz besonders bevorzugt ist die erfindungsgemäße Verwendung von Verbindungen der allgemeinen Formel (I), worin Very particular preference is given to the use according to the invention of compounds of the general formula (I) in which
[X-Y] für die Gruppierung [X-Y] for grouping
[x-Y]1 steht, Q für die Gruppierungen Q-1 bis Q-6 [xY] 1 , Q stands for the groupings Q-1 to Q-6
sieht, wobei R7, R8, R9, R10, R11, R12, R13, R14, R17, R18, R19, R20, R22, R23, R24, R25, R26, R28, R29 und R30 und A1 bis A9 jeweils die Bedeutung gemäß der nachstehenden Definitionen haben und wobei der Pfeil für eine Bindung zur jeweiligen Gruppierung C-R6 in der allgemeinen Formel (I) steht, where R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 17 , R 18 , R 19 , R 20 , R 22 , R 23 , R 24 , R 25 , R 26 , R 28 , R 29 and R 30 and A 1 to A 9 each have the meaning according to the definitions below and wherein the arrow for a bond to the respective group CR 6 in the general formula (I),
R1 für (Ci-Ce)-Alkyl, (C3-C6)-Cycloalkyl, (C4-C6)-Cycloalkenyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (C2-C6)-Alkenyl-(Ci-C6)-alkyl, (C2-C6)-Alkinyl-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, Hydroxy-(Ci-C6)-alkyl, (Ci-C6)-Haloalkyl, (C2-C6)- Haloalkenyl, (C2-C6)-Haloalkinyl steht, R 1 is (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, (C 4 -C 6 ) -cycloalkenyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl , (C 2 -C 6) alkenyl (Ci-C 6) alkyl, (C2-C6) alkynyl (Ci-C 6) alkyl, (Ci-C 6) alkoxy (Ci- C 6) alkyl, hydroxy (Ci-C 6) alkyl, (Ci-C 6) -haloalkyl, (C 2 -C 6) - haloalkenyl, (C 2 -C 6) haloalkynyl group,
R2, R3 und R4 unabhängig voneinander für Wasserstoff, Fluor, (Ci-Cc)-Alkyl, (Ca-Ce)-R 2 , R 3 and R 4 independently of one another represent hydrogen, fluorine, (C 1 -C 6) -alkyl, (Ca-Ce) -
Cycloalkyl, (C4-C6)-Cycloalkenyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (C2-C6)- Alkenyl-(Ci-C6)-alkyl, (C2-C6)-Alkinyl-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, Hydroxy-(Ci-C6)-alkyl, (Ci-C6)-Haloalkyl stehen,
für Hydroxy, (d-CeJ-Alkoxy, Aryloxy, (C3-Cc,)-Cycloalkyloxy, (C2-C6)-Alkenyloxy, Cycloalkyl, (C 4 -C 6 ) cycloalkenyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (C 2 -C 6 ) alkenyl (C 1 -C 6 ) alkyl , (C 2 -C 6) alkynyl (Ci-C 6) alkyl, (Ci-C6) alkoxy (Ci-C 6) alkyl, hydroxy (Ci-C 6) alkyl, ( Ci-C 6 ) -haloalkyl, hydroxy, (d-CeJ-alkoxy, aryloxy, (C3-Cc,) - cycloalkyloxy, (C 2 -C 6) alkenyloxy,
(C2-C6)-Alkenyl-(Ci-C6)-alkyloxy, (Ci-C6)-Alkoxy-(Ci-C6)-alkyloxy, (Ci-C6)- Alkylcarbonyloxy, Arylcarbonyloxy, Heteroarylcarbonyloxy, (C3-Ce)- Cycloalkylcarbonyloxy, (Ci-Ce)-Alkoxycarbonyloxy, (d-Ce)- Alkenyloxycarbonyloxy, Aryloxy-(Ci-C6)-alkyloxy, Aryl-(Ci-C6)-alkyloxy, (Ci-Ce)- Alkoxy-(Ci-C6)-alkoxy-(Ci-C6)-alkyloxy, (Ci-C6)-Alkylthio-(Ci-C6)-alkyloxy, Tris[(Ci-C6)-alkyl]silyloxy, (Ci-C6)-Alkyl-Bis[(Ci-C6)-alkyl]silyloxy, (Ci-C6)-Alkyl- bis(Aryl)silyloxy, Aryl-bis[(Ci-Ce)— alkyljsilyloxy, Cycloalkyl-bis[(Ci-C-6)- alkyljsilyloxy, Halo-bis[(Ci-C6)-alkyl]silyloxy, Tris[(Ci-C6)-alkyl]silyl-(Ci-C6)- alkoxy-(Ci-C6)-alkyloxy, steht, (C 2 -C 6) alkenyl (Ci-C 6) alkyloxy, (Ci-C6) alkoxy (Ci-C 6) alkyloxy, (Ci-C 6) - alkylcarbonyloxy, arylcarbonyloxy, heteroarylcarbonyloxy, (C3-Ce) -cycloalkylcarbonyloxy, (Ci-Ce) -alkoxycarbonyloxy, (d-Ce) -alkenyloxycarbonyloxy, aryloxy- (Ci-C6) -alkyloxy, aryl- (Ci-C6) -alkyloxy, (Ci-Ce) - Alkoxy- (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyloxy, (C 1 -C 6 ) -alkylthio (C 1 -C 6 ) -alkyloxy, tris [(C 1 -C 6 ) -alkyl] silyloxy , (C 1 -C 6 ) -alkyl-bis [(C 1 -C 6 ) -alkyl] silyloxy, (C 1 -C 6 ) -alkyl-bis (aryl) silyloxy, aryl-bis [(C 1 -C 6 ) -alkyl] ssilyloxy, Cycloalkyl-bis [(Ci-C-6) alkylsilyloxy, halo-bis [(Ci-C 6 ) alkyl] silyloxy, tris [(Ci-C6) alkyl] silyl (Ci-C 6 ) alkoxy (C 1 -C 6) -alkyloxy,
R6 für Nitro, Amino, Hydroxy, Hydrothio, Thiocyanato, Isothiocyanato, Fluor, Chlor,R 6 for nitro, amino, hydroxy, hydrothio, thiocyanato, isothiocyanato, fluorine, chlorine,
Brom, lod, (Ci-C6)-Alkyl, (C3-C6)-Cycloalkyl, (C2-C6)-Alkenyl, (C4-C6)- Cycloalkenyl, (C2-C6)-Alkinyl, Aryl-(C2-C6)-alkinyl, Tris[(Ci-C6)-alkyl]silyl-(C2-C6)- alkinyl, Aryl, Aryl-(CrC6)-alkyl, Aryl-(CrC6)-alkoxy, Heteroaryl, (Ci-C6)-Bromine, iodine, (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, (C 2 -C 6 ) -alkenyl, (C 4 -C 6 ) -cycloalkenyl, (C 2 -C 6 ) alkynyl, aryl (C 2 -C 6) -alkynyl, tris [(Ci-C6) alkyl] silyl (C 2 -C 6) - alkynyl, aryl, aryl (CrC 6) alkyl, aryl (C 1 -C 6 ) -alkoxy, heteroaryl, (C 1 -C 6 ) -
Haloalkyl, (C3-C6)-Halocycloalkyl, (C2-C6)-Haloalkenyl, (Ci-C6)-Alkoxy, (Ci-C6)- Haloalkoxy, Aryloxy, Heteroaryloxy, (C3-C6)-Cycloalkyloxy, (C3-Cö)-Cycloalkyl- (CrC6)-alkoxy, (C2-C6)- (C2-C6)-Alkenyloxy, (C2-C6)-Alkinyl-(C2-C6)-alkyloxy, Hydroxy-(CrC6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, Aryloxy-(Ci-C6)-alkyl,
Heieroaryloxy-(Ci-C6)-alkyl, (Ci-C6)-Alkylthio, (Ci-Ce)-Haloalkylthio, (Ci-Ce)- Alkoxycarbonyl-(Ci-C6)-alkylthio, Aryithio, (Ca-CeJ-Cycloalkylthio, Heteroarylthio, (Ci-C6)-Alkylthio-(Ci-C6)-alkyl, (Ci-C6)-Alkylamino, Bis[(Ci-C6)-alkyl]amino, (C2-C6)-Alkenylamino, (C3-C6)-Cycloalkylamino, (Ci-Cc -Alkylcarbonylamino, (C3-C6)-Cycloalkylcarbonylamino, Arylcarbonylamino, Heteroarylcarbonylamino, Formylamino, (Ci-CeJ-Haloalkylcarbonylamino, (CrC6)-Alkoxycarbonylamino, (Ci-Cc^-Alkylaminocarbonylamino, (Ci-C6)-Alkyl[(d-C6)- Alkyl]aminocarbonylamino, (Ci-C6)-Alkylsulfonylamino, (Ca-Co)- Cycloalkylsulfonylamino, Arylsulfonylamino, Hetarylsulfonylamino, Sulfonyl- (Ci-C6)-haloalkylamino, Amino-(Ci-C6)-alkylsulfonyl, Amino-(Ci-C6)- haloalkylsulfonyl, (Ci-Cc -Alkylaminosulfonyl, Bis[(Ci-C6)-alkyl]aminosulfonyl, (Ca-Ce Cycloalkylaminosulfonyl, (Ci-C6)-Haloalkylaminosulfonyl, Aminosuifonyl, Heteroarylaminosulfonyl, Arylaminosulfonyl, Aryl-(Ci-C6)-alkylaminosulfonyl, (Ci-C6)-Alkylsulfonyl, (C3-C6)-Cycloalkylsulfonyl, Arylsulfonyl, (Ci-C6)- Alkylsulfinyl, (C3-C6)-Cycloalkylsulfinyl, Arylsulfinyl, N.S-Bis[(Ci-C6)- alkyl]sulfonimidoyl, S-(CrC6)-Alkylsulfonimidoyl, (d-Cö)- Alkylsulfonylaminocarbonyl, (Ca-CoJ-Cycloalkylsulfonylaminocarbonyl, Aryl- (Ci-C6)-alkylcarbonylamino, (C3-C6)-Cycloalkyl-(Ci-C6)-alkylcarbonylamino, Heteroarylcarbonylamino, (Ci-C6)-Alkoxy-(Ci-C6)-alkylcarbonylamino, Hydroxy- (Ci-C6)-alkylcarbonylamino, (Ci-C6)-Alkoxycarbonylamino-(Ci-C6)- alkylcarbonylamino, Cyano, Cyano-(d-C6)-alkyl, Hydroxycarbonyl, (d-Co)- Alkoxycarbonyl, (Ca-CeJ-Cycloalkoxycarbonyl, (C3-C6)-Cycloalkyl-(Ci-C6)- alkoxycarbonyl, Aryloxycarbonyl, Aryl-(Ci-C6)-alkoxycarbonyl, (C2-Ce)- Alkenyloxycarbonyl, (C2-C6)-Alkinyloxycarbonyl, (d-C6)-Haloalkyloxycarbonyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkoxycarbonyl, (C2-C6)-Alkenyloxy-(Ci-C6)- alkoxycarbonyl, (Ci-Cö)-Alkylamino-(Ci-C6)-alkoxycarbonyl, Tris[(d-C6)- alkyl]silyloxy-(Ci-Cö)-alkoxycarbonyl, Bis[(Ci-C6)-Alkyl]amino-(Ci-C6)- alkoxycarbonyl, (Ci-C6)-Alkyl[(Ci-C6)-alkyl]amino-(Ci-C6)-alkoxycarbonyl, Cyano-(Ci-C6)-alkoxycarbonyl, Heterocyclyl-N-(Ci-C6)-alkoxycarbonyl, Haloalkyl, (C 3 -C 6) halocycloalkyl, (C 2 -C 6) haloalkenyl, (Ci-C 6) alkoxy, (Ci-C6) - haloalkoxy, aryloxy, heteroaryloxy, (C3-C6) - Cycloalkyloxy, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkoxy, (C 2 -C 6 ) - (C 2 -C 6 ) -alkenyloxy, (C 2 -C 6 ) -alkynyl- (C 2 -C 6 ) -alkyloxy, hydroxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, aryloxy- (C 1 -C 6 ) -alkyl, Heoaryloxy- (Ci-C 6 ) alkyl, (Ci-C 6 ) -alkylthio, (Ci-Ce) -haloalkylthio, (Ci-Ce) - alkoxycarbonyl- (Ci-C6) -alkylthio, Aryithio, (Ca-CeJ -Cycloalkylthio, heteroarylthio, (C 1 -C 6 ) -alkylthio (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylamino, bis [(C 1 -C 6 ) -alkyl] -amino, (C 2 -C 6 ) Alkenylamino, (C 3 -C 6) -cycloalkylamino, (C 1 -C 6 -alkylcarbonylamino, (C 3 -C 6) -cycloalkylcarbonylamino, arylcarbonylamino, heteroarylcarbonylamino, formylamino, (C 1 -C 6 -haloalkylcarbonylamino, (C 1 -C 6) -alkoxycarbonylamino, (C 1 -C 6) -cycloalkylcarbonylamino) -Alkylaminocarbonylamino, (C 1 -C 6) -alkyl [(C 1 -C 6) -alkyl] aminocarbonylamino, (C 1 -C 6) -alkylsulfonylamino, (Ca-Co) -cycloalkylsulfonylamino, arylsulfonylamino, hetarylsulfonylamino, sulfonyl- (C 1 -C 6) -haloalkylamino , Amino- (C 1 -C 6) -alkylsulfonyl, amino- (C 1 -C 6) -haloalkylsulfonyl, (C 1 -C 6 -alkylaminosulfonyl, bis [(C 1 -C 6) -alkyl] aminosulfonyl, (C 1 -C 6 -cycloalkylaminosulfonyl, (C 1 -C 6) ) -Haloalkylaminosulfonyl, aminosulfonyl, heteroarylaminosulfonyl, arylaminosulfonyl, aryl- (C 1 -C 6 ) -alkylaminosulfonyl, (C 1 -C 6 ) -alkylsulfonyl , (C 3 -C 6) cycloalkylsulfonyl, arylsulfonyl, (Ci-C 6) - alkylsulfinyl, (C3-C 6) cycloalkylsulfinyl, arylsulfinyl, NS-bis [(Ci-C 6) - alkyl] sulfonimidoyl, S- (C 1 -C 6) -alkylsulfonimidoyl, (C 1 -C 6) -alkylsulfonylaminocarbonyl, (C 1 -C 6 -cycloalkylsulfonylaminocarbonyl, aryl- (C 1 -C 6) -alkylcarbonylamino, (C 3 -C 6) -cycloalkyl- (C 1 -C 6) -alkylcarbonylamino, heteroarylcarbonylamino, ( C 1 -C 6) -alkoxy- (C 1 -C 6) -alkylcarbonylamino, hydroxy- (C 1 -C 6) -alkylcarbonylamino, (C 1 -C 6) -alkoxycarbonylamino- (C 1 -C 6) -alkylcarbonylamino, cyano, cyano- (d-C 6) -alkyl, hydroxycarbonyl, (d-Co) - alkoxycarbonyl, (Ca-CeJ-cycloalkoxycarbonyl, (C3-C6) -cycloalkyl- (Ci-C6) -alkoxycarbonyl, aryloxycarbonyl, aryl- (Ci-C6) -alkoxycarbonyl, (C2 -ce) - alkenyloxycarbonyl, (C2-C6) -alkynyloxycarbonyl, (d-C6) -Haloalkyloxycarbonyl, (Ci-C6) alkoxy (Ci-C 6) -alkoxycarbonyl, (C2-C6) alkenyloxy ( C 1 -C 6 ) -alkoxycarbonyl, (C 1 -C 6 ) -alkylamino- (C 1 -C 6 ) -alkoxycarbonyl, tris [(C 1 -C 6 ) -alkyl] silyloxy- (C 1 -C 6) -alkoxycarbonyl, bis [(C 1 -C 6 ) alkyl] amino- (Ci-C6) - alkoxycarbonyl, (C 1 -C 6) -alkyl [(C 1 -C 6) -alkyl] amino- (C 1 -C 6) -alkoxycarbonyl, cyano- (C 1 -C 6) -alkoxycarbonyl, heterocyclyl-N- (C 1 -C 6) -alkoxycarbonyl,
Heteroaryloxycarbonyi, Heteroaryl-(Ci-C6)-alkoxycarbonyl, Heterocyclyl-(Ci-Cc>)- alkoxycarbonyl, Heterocyclyloxycarbonyl, (C2-C6)-Alkenyl-(Ci-Cr,)- alkoxycarbonyl, (C2-C6)-Alkinyl-(d-C6)-alkoxycarbonyl, Aryl-(C2-Ce)- alkinyloxycarbonyl, Aryl-(C2-C6)-alkenyloxycarbonyl, Aminocarbonyl, (Ci-Ce)- Alkylaminocarbonyl, Bis[(Ci-C6)-alkyl]aminocarbonyl, (Ci-C6)-Alkyl[(d-C6)-
Alkyljaminocarbonyl, (Ci-C6)-Alkyl[(Ci-C6)-Alkoxy]aminocarbonyl, (Cz-Ce)- Alkenylaminocarbonyl, (Cs-d -Cycloalkylaminocarbonyl, Arylaminocarbonyl, Aryl-(Ci-C6)-alkylaminocarbonyl, Heteroaryl-(Ci-C6)-alkylaminocarbonyL Cyano- (Ci-Cö)-alkylaminocarbonyl, (Ci-C6)-Haloalkylaminocarbonyl, (C2-Cr,)-Alkinyl- (CrCe alkylaminocarbonyl, (CrCr -Alkoxycarbonylaminocarbonyl, Aryl-(d-C6)- alkoxycarbonylaminocarbonyl, Hydroxycarbonyl-(Ci-C6)-alkyl, (d-Ce)- Alkoxycarbonyl-(d-C6)-alkyl, (C3-Cr>)-Cycloalkoxycarbonyl-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkoxycarbonyl-(Ci-C6)-alkyl, (C2-C6)- Alkenyloxycarbonyl-(Ci-C6)-alkyl, Aryl-(Ci-C6)-alkoxycarbonyl-(Ci-Cö)-alkyl, (Ci-C6)-Alkylaminocarbonyl-(Ci-Cr>)-alkyl, Aminocarbonyl-(Ci-C6)-alkyl, Heteroaryloxycarbonyi, heteroaryl (Ci-C6) -alkoxycarbonyl, heterocyclyl (Ci-Cc>) - alkoxycarbonyl, Heterocyclyloxycarbonyl, (C2-C6) alkenyl (C Cr) - alkoxycarbonyl, (C2-C6) -alkynyl (C 1 -C 4) -alkoxycarbonyl, aryl- (C 2 -C 6) -alkynyloxycarbonyl, aryl- (C 2 -C 6) -alkenyloxycarbonyl, aminocarbonyl, (C 1 -C 6) -alkylaminocarbonyl, bis [(C 1 -C 6) -alkyl] aminocarbonyl, (Ci-C6) alkyl [(d-C6) - (C 1 -C 6) -alkyl [(C 1 -C 6) -alkoxy] -aminocarbonyl, Ci-C6) -alkylaminocarbonyL cyano- (Ci-Cö) -alkylaminocarbonyl, (Ci-C6) -haloalkylaminocarbonyl, (C2-Cr,) - alkynyl- (CrCe alkylaminocarbonyl, (CrCr-alkoxycarbonylaminocarbonyl, aryl- (d-C6) - alkoxycarbonylaminocarbonyl, hydroxycarbonyl- (Ci-C6) alkyl, (d-Ce) - alkoxycarbonyl (d-C6) alkyl, (C3-Cr>) -Cycloalkoxycarbonyl- (Ci-C6) alkyl, (C3-C6) cycloalkyl (Ci-C 6) alkoxycarbonyl (Ci-C6) alkyl, (C 2 -C 6) - alkenyloxycarbonyl (Ci-C6) alkyl, aryl (Ci-C6) alkoxycarbonyl (C -Cö) alkyl, (Ci-C6) alkylaminocarbonyl (Ci-Cr>) alkyl, aminocarbonyl (Ci-C6) alkyl,
Bis[(Ci-C6)-alkyl]aminocarbonyl-(Ci-C6)-alkyl, (Ca-CeJ-Cycloalkylaminocarbonyl- (Ci-C6)-alkyl, Aryl-(Ci-C6)-alkylaminocarbonyl-(Ci-C6)-alkyl, Heteroaryl-(CrC6)- alkylaminocarbonyl-(Ci-C6)-alkyl, Cyano-(Ci-C6)-alkylaminocarbonyl-(Ci-C6)- alkyl, (Ci-C6)-Haloalkylaminocarbonyl-(Ci-C6)-alkyl, (C2-C6)-Alkinyl-(Ci-C6)- alkylaminocarbonyl-(CrC6)-alkyl, (C3-Cr>)-Cycloalkyl-(Ci-C6)- alkylaminocarbonyl-(Ci-C6)-alkyl, (d-CeJ-Alkoxycarbonylaminocarbonyl- (Ci-C6)-alkyl, Aryl-(Ci-C6)-alkoxycarbonylaminocarbonyl-(Ci-C6)-alkyl, (d-Ce)- Alkoxycarbonyl-(Ci-Cö)-alkylaminocarbonyl, Hydroxycarbonyl-(Ci-C6)- alkylaminocarbonyl, Aryl-(Ci-C6)-alkoxycarbonyl-(Ci-C6)-alkylaminocarbonyl, (Ci-C6)-Alkoxycarbonyl-heterocyclyl-N-carbonyl, (Ci-C6)-Alkoxycarbonyl-(Ci- C6)-alkyl-heterocyclylidenaminocarbonyl, (d-Ce)- Alkoxycarbonylheterocyclyliden-(Ci-C6)-alkylaminocarbonyl (d-Ce)- Alkoxycarbonyl-(Ci-C6)-Alkyl((Ci-C6)-alkyl)aminocarbonyl, (Ci-Ce)- Alkoxycarbonyl-(C3-C6)-cycloalkylidenaminocarbonyl, Heterocyclyl-N-carbonyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkylaminocarbonyl, Aminocarbonyl-(Ci-C6)- alkylaminocarbonyl, (Ci-C6)-Alkylaminocarbonyl-(Ci-C6)-alkylaminocarbonyl, (C3-C6)-Cycloalkylaminocarbonyl-(Ci-C6)-alkylaminocarbonyl, (d-Ce)- Cycloalkyl-(Ci-C6)-alkylaminocarbonyl, (C3-C6)-Cycloalkyl-(Ci-C6)- alkylaminocarbonyl-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl-(Ci-C6)- alkylaminocarbonyl-(Ci-C6)-alkylaminocarbonyl, (C2-C6)-Alkenyl-(Ci-Cc>)- alkylaminocarbonyl, (C2-Ce)-Alkenylaminocarbonyl-(Ci-C6)-alkyl, (C2-C-6)- Alkenyl-(Ci-C6)-alkylaminocarbonyl-(Ci-C6)-alkyl, (Ci-C6)-Alkylcarbonyl, (C3-C6)- Cycloalkylcarbonyl, Arylcarbonyl, Formyl, Hydroxyiminomethyl, Bis [(C 1 -C 6 ) -alkyl] aminocarbonyl- (C 1 -C 6 ) -alkyl, (C 1 -C 12 -cycloalkylaminocarbonyl- (C 1 -C 6 ) -alkyl, aryl- (C 1 -C 6 ) -alkylaminocarbonyl- (C 1 -C 4 ) -alkyl) C 6 ) -alkyl, heteroaryl- (C 1 -C 6 ) -alkylaminocarbonyl- (C 1 -C 6 ) -alkyl, cyano- (C 1 -C 6 ) -alkylaminocarbonyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkylaminocarbonyl- (Ci -C 6) alkyl, (C2-C6) alkynyl (Ci-C6) - alkylaminocarbonyl (CRC6) alkyl, (C3-Cr>) cycloalkyl (Ci-C6) - alkylaminocarbonyl (Ci -C 6) -alkyl, (d-CeJ-alkoxycarbonylaminocarbonyl- (C 1 -C 6) -alkyl, aryl- (C 1 -C 6) -alkoxycarbonylaminocarbonyl- (C 1 -C 6) -alkyl, (C 1 -C 6) -alkoxycarbonyl- (C 1 -C 4) alkyl) C 6) -alkylaminocarbonyl, hydroxycarbonyl- (C 1 -C 6) -alkylaminocarbonyl, aryl- (C 1 -C 6) -alkoxycarbonyl- (C 1 -C 6) -alkylaminocarbonyl, (C 1 -C 6) -alkoxycarbonyl-heterocyclyl-N-carbonyl, C 6) alkoxycarbonyl- (C 1 -C 6) -alkyl-heterocyclylideno-aminocarbonyl, (d-Ce) -alkoxycarbonyl-heterocyclylidene- (C 1 -C 6) -alkylaminocarbonyl (d-Ce) -alkoxycarbonyl- (C 1 -C 6) -alkyl ((C 1 -C 6) -alkoxycarbonyl) ) -alkyl) aminocarbonyl, (Ci-Ce) - alkoxycarbonyl- (C3-C6) -cycloalkylidenaminocarbonyl, Heter ocyclyl-N-carbonyl, (C 1 -C 6) -alkoxy- (C 1 -C 6) -alkylaminocarbonyl, aminocarbonyl- (C 1 -C 6) -alkylaminocarbonyl, (C 1 -C 6) -alkylaminocarbonyl- (C 1 -C 6) -alkylaminocarbonyl, (C3 -C6) -cycloalkylaminocarbonyl- (Ci-C6) -alkylaminocarbonyl, (d-Ce) -cycloalkyl- (Ci-C6) -alkylaminocarbonyl, (C3-C6) -cycloalkyl- (Ci-C6) - alkylaminocarbonyl- (Ci-C6 ) -alkyl, (C3-C6) -cycloalkyl- (Ci-C6) -alkylaminocarbonyl- (Ci-C6) -alkylaminocarbonyl, (C2-C6) -alkenyl- (Ci-Cc > ) - alkylaminocarbonyl, (C2-Ce) Alkenylaminocarbonyl- (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl- (C 1 -C 6 ) -alkylaminocarbonyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylcarbonyl, (C 3 -C 6 ) - cycloalkylcarbonyl, arylcarbonyl, formyl, hydroxyiminomethyl,
Aminoiminomethyl, (Ci-C6)-Alkoxyiminomethyl, (Ci-C6)-Alkylaminoiminomethyl,
Bis[(Ci-C6)-alkyl]aminoiminomethyl, (C3-C6)-Cycloalkoxyiminomethyl, (Ca-Ce)- Cycloalkyl-(Ci-C6)-alkoximinomethyl, Aryloximinomethyl, Aryl-(Ci-Ce)- alkoxyiminomethyl, Aryl-(Ci-C6)-alkylaminoiminomethyl, (C2-Ce)- Alkenyloxyiminomethyl, Aryiaminoiminomethyl, Arylsulfonylaminoiminomethyl, Heteroaryl-(Ci-C6)-alkyl, Heterocyclyl-(Ci-C6)-alkyl, Aminoiminomethyl, (C 1 -C 6) -alkoxyiminomethyl, (C 1 -C 6) -alkylaminoiminomethyl, Bis [(C 1 -C 6) -alkyl] aminoiminomethyl, (C 3 -C 6) -cycloalkoxyiminomethyl, (Ca-Ce) -cycloalkyl- (C 1 -C 6) -alkoximinomethyl, aryloximinomethyl, aryl- (C 1 -C 6) -alkoxyiminomethyl, aryl- (C 1 -C 6 ) -alkylaminoiminomethyl, (C 2 -C 6 ) -alkenyloxyiminomethyl, aryiaminoiminomethyl, arylsulfonylaminoiminomethyl, heteroaryl- (C 1 -C 6 ) -alkyl, heterocyclyl- (C 1 -C 6 ) -alkyl,
Hydroxycarbonylheterocyclyl, (Ci-C6)-Alkoxycarbonylheterocyclyl, (C2-C6)- Alkenyloxycarbonylheterocyclyl, (C2-C6)-Alkenyl-(Ci-Cr,)- alkoxycarbonylheterocyclyl, Aryl-(Ci-Cr,)-alkoxycarbonylheterocyclyl, (Ca-Ce)- Cycloalkoxycarbonylheterocyclyl, (Ca-C6)-Cycloalkyl-(Ci-C6)- alkoxycarbonylheterocyclyl, Aminocarbonylheterocyclyl, (Ci-Cr>)- Alkylaminocarbonylheterocyclyl, Bis[(Ci-C6)-Alkyl]aminocarbonylheterocyclyl, (C3-C6)-Cycloalkylaminocarbonylheterocyclyl, Aryl-(Ci-Ce)- alkylaminocarbonylheterocyclyl, (C2-C6)-Alkenylaminocarbonylheterocyclyl, Hydroxycarbonylheterocyclyl-(Ci-Cc,)-alkyl, (CrCr -Alkoxycarbonylheterocyclyl- (Ci-C6)-alkyl, Hydroxycarbonyl-(C3-C6)-cycloalkyl-(Ci-C6)-alkyl, (Ci-C6)- Alkoxycarbonyl-(C3-C6)-cycloalkyl-(Ci-Cö)-alkyl, Hydroxyaminocarbonyl, (d-C6)-Alkoxyaminocarbonyl, Aryl-(d-C6)-alkoxyaminocarbonyl, Heterocyclyl, (Ci-C6)-Alkylcarbonyloxy, Arylcarbonyloxy, Heteroarylcarbonyloxy, (Ca-Ce)- Cycloalkylcarbonyloxy, (Ci-C6)-Alkoxycarbonyloxy, (C2-C6)- Alkenyloxycarbonyloxy steht, Hydroxycarbonylheterocyclyl, (C 1 -C 6) -alkoxycarbonylheterocyclyl, (C 2 -C 6) -alkenyloxycarbonylheterocyclyl, (C 2 -C 6) -alkenyl- (C 1 -C 8) -alkoxycarbonylheterocyclyl, aryl- (C 1 -C 8) -alkoxycarbonylheterocyclyl, (Ca-Ce ) - Cycloalkoxycarbonylheterocyclyl, (Ca-C6) -cycloalkyl- (Ci-C6) -alkoxycarbonylheterocyclyl, aminocarbonylheterocyclyl, (Ci-Cr > ) - alkylaminocarbonylheterocyclyl, bis [(Ci-C6) -alkyl] aminocarbonylheterocyclyl, (C3-C6) -cycloalkylaminocarbonylheterocyclyl , aryl (Ci-Ce) - alkylaminocarbonylheterocyclyl, (C2-C6) -Alkenylaminocarbonylheterocyclyl, Hydroxycarbonylheterocyclyl- (Ci-Cc,) - alkyl, (CrCr -Alkoxycarbonylheterocyclyl- (Ci-C 6) alkyl, hydroxycarbonyl (C3-C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxycarbonyl- (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, hydroxyaminocarbonyl, (C 1 -C 6 ) -alkoxyaminocarbonyl, aryl - (C 1 -C 6) alkoxyaminocarbonyl, heterocyclyl, (C 1 -C 6) -alkylcarbonyloxy, arylcarbonyloxy, heteroarylcarbonyloxy, (Ca-Ce) -cycloalkylcarbonyloxy, (C 1 -C 6) -alkoxycarbonyloxy, (C 2 -C 6) -alkenylox ycarbonyloxy stands,
R7, R8 , R9 und R10 unabhängig voneinander für Wasserstoff, Fluor, Chlor, Brom, lod, Nitro, Amino, Cyano,
gegebenenfalls substituiertes Phenyl , Heteroaryi, (C3-C6)-Cycloalkyl, (C4-C6)-Cycloalkenyl, (C2-C6)-Alkenyl, (C2-C6)- Alkinyl, (C2-C6)-Alkenyl-(Ci-C6)-alkyl, (C2-C6)-Alkinyl-(Ci-C6)-alkyl, Hydroxy, (Ci-C6)-Alkoxy, (Ci-C6)-Alkoxy-(Ci-C6)-alkoxy, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, Hydroxy-(Ci-C6)-alkyl, (Ci-C6)-Haloalkoxy, (Ci-C6)-Haloalkyl, (C2-C6)- Haloalkenyl, (C2-C6)-Haloalkinyl, (Ci-C6)-Haloalkoxy-(Ci-C6)-alkyl, (Ci-C6)- Alkoxy-(Ci-C6)-haloalkyl, (Ci-C6)-Haloalkoxy-(Ci-C6)-haloalkyl, Hydrothio, R 7 , R 8 , R 9 and R 10 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, nitro, amino, cyano, optionally substituted phenyl, heteroaryl, (C 3 -C 6 ) -cycloalkyl, (C 4 -C 6 ) -cycloalkenyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, (C 2 -C 6 ) -alkenyl- (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkynyl- (C 1 -C 6 ) -alkyl, hydroxy, (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) - Alkoxy- (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, hydroxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkoxy, ( Ci-C 6) -haloalkyl, (C 2 -C 6) - haloalkenyl, (C2-C6) haloalkynyl, (Ci-C 6) haloalkoxy (Ci-C 6) alkyl, (Ci-C 6) Alkoxy- (C 1 -C 6 ) -haloalkyl, (C 1 -C 6 ) -haloalkoxy- (C 1 -C 6 ) -haloalkyl, hydrothio,
(CrC6)-Alkylthio, (CrC6)-Haloalkylthio, (Ci-C6)-Alkylthio-(Ci-C6)-alkyl, (CrC6)- Haloalkylthio-(Ci-C6)-alkyl, (Ci-C6)-Alkylamino, Bis[(Ci-C6)-alkyl]amino, (C2-C6)- Alkenylamino, (Ca-Cc -Cycloalkylamino, (Ci-C6)-Alkylcarbonylamino, (Ca-Ce)- Cycloalkylcarbonylamino, Arylcarbonylamino, Heteroarylcarbonylamino, Formylamino, (Ci-C6)-Haloalkylcarbonylamino, (Ci-C6)-Alkoxycarbonylamino,
(Ci-C6)-Alkylaminocarbonylamino, (Ci-C6)-Alkyl[(Ci-C6)- Alkyl]aminocarbonylamino, (d-Ce Alkylsulfonylamino, (Ca-Ce)- Cycloalkylsulfonylamino, Arylsulfonylamino, Hetarylsulfonylamino, Sulfonyl- (CrCe haloalkylamino, Amino-(CrC6)-alkylsulfonyi, Amino-(Ci-C-6)- haloalkylsulfonyl, (CrC6)-Alkylaminosulfonyl, Bis[(CrC6)-alkyl]aminosulfonyl, (Ca-CeJ-Cycloalkylaminosulfonyl, (Ci-C6)-Haloalkylaminosulfonyl, (CrC 6) alkylthio, (CrC 6) haloalkylthio, (Ci-C 6) alkylthio (Ci-C 6) alkyl, (CrC 6) - Haloalkylthio- (Ci-C 6) alkyl, (C -C 6 ) -alkylamino, bis [(Ci-C 6 ) -alkyl] amino, (C 2 -C 6 ) -alkenylamino, (Ca-Cc -cycloalkylamino, (Ci-C6) -alkylcarbonylamino, (Ca-Ce) Cycloalkylcarbonylamino, arylcarbonylamino, heteroarylcarbonylamino, formylamino, (C 1 -C 6) -haloalkylcarbonylamino, (C 1 -C 6) -alkoxycarbonylamino, (C 1 -C 6) -alkylaminocarbonylamino, (C 1 -C 6) -alkyl [(C 1 -C 6) -alkyl] aminocarbonylamino, (C 1 -C 6 -alkylsulfonylamino, (C 1 -C 6) -cycloalkylsulfonylamino, arylsulfonylamino, hetarylsulfonylamino, sulfonyl- (C 1 -C 6 -alkylamino) Amino (C 1 -C 6) alkylsulfonyi, amino (C 1 -C 6) haloalkylsulfonyl, (C 1 -C 6) alkylaminosulfonyl, bis [(C 1 -C 6) alkyl] aminosulfonyl, (C 1 -C 12 -cycloalkylaminosulfonyl, (C 1 -C 6) -haloalkylaminosulfonyl .
Heteroarylaminosulfonyl, Arylaminosulfonyl, Aryl-(Ci-C6)-alkylaminosulfonyl, (d-Cr-Alkylsulfonyl, (C3-C6)-Cycloalkylsulfonyl, Arylsulfonyl, Hydroxycarbonyl, (Ci-C6)-Alkoxycarbonyl, (Cs-d -Cycloalkoxycarbonyl, (Ca-Q -Cycloalkyl- (Ci-C6)-alkoxycarbonyl, Aryloxycarbonyl, Aryl-(Ci-C6)-alkoxycarbonyl, (C2-C6)- Alkenyloxycarbonyl, (C2-C6)-Alkinyloxycarbonyl, Aminocarbonyl, (d-Ce)- Alkylaminocarbonyl, Bis[(Ci-C6)-alkyl]aminocarbonyl, (Ci-C6)-Alkyl[(d-C6)- Alkyl]aminocarbonyl, (Ci-C6)-Alkyl[(Ci-C6)-Alkoxy]aminocarbonyl, (C2-C6)- Alkenylaminocarbonyl, (C3-Cö)-Cycloalkylaminocarbonyl, Arylaminocarbonyl, Aryl-(Ci-C6)-alkylaminocarbonyl stehen, Heteroarylaminosulfonyl, arylaminosulfonyl, aryl- (Ci-C6) -alkylaminosulfonyl, (d-Cr-alkylsulfonyl, (C3-C6) -cycloalkylsulfonyl, arylsulfonyl, hydroxycarbonyl, (Ci-C6) -alkoxycarbonyl, (Cs-d-cycloalkoxycarbonyl, (Ca -Q-cycloalkyl- (C 1 -C 6) alkoxycarbonyl, aryloxycarbonyl, aryl- (C 1 -C 6) alkoxycarbonyl, (C 2 -C 6) alkenyloxycarbonyl, (C 2 -C 6) alkynyloxycarbonyl, aminocarbonyl, (d-Ce) -alkylaminocarbonyl , Bis [(C 1 -C 6) -alkyl] aminocarbonyl, (C 1 -C 6) -alkyl [(C 1 -C 6) -alkyl] aminocarbonyl, (C 1 -C 6) -alkyl [(C 1 -C 6) -alkoxy] -aminocarbonyl, ( C 2 -C 6) - alkenylaminocarbonyl, (C 3 -C 6) -cycloalkylaminocarbonyl, arylaminocarbonyl, aryl- (C 1 -C 6) -alkylaminocarbonyl,
A1, A2, A3 und A4 gleich oder verschieden sind und unabhängig voneinander für NA 1 , A 2 , A 3 and A 4 are the same or different and are independently N
(Stickstoff) oder die Gruppierungen C-H, C-CH3, C-F, C-Cl, C-Br, C-l, C-OCF3, C-OCH3, C-CF3, C-CO2H, C-CO2CH3 stehen, wobei jedoch in keinem Fall mehr als zwei N-Atome benachbart sind, (Nitrogen) or the groups CH, C-CH 3 , CF, C-Cl, C-Br, Cl, C-OCF3, C-OCH3, C-CF3, C-CO2H, C-CO2CH3, but in no Case more than two N atoms are adjacent,
R11 und R12 unabhängig voneinander für Wasserstoff, Fluor, Chlor, Brom, lod, (d-Ce)- Alkyl, gegebenenfalls substituiertes Phenyl, Heteroaryl, Heterocyclyl, (C3-C6)- Cycloalkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, Aryloxy-(Ci-C6)-alkyl, (Ci-C6)-Haloalkyl, (Ci-C6)-Haloalkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-haloalkyl, (Ci-C6)-Haloalkoxy-(Ci-C6)-haloalkyl, (d-C6)- Alkylthio-(Ci-Ce)-alkyl, Hydroxycarbonyl, (Ci-C6)-Alkoxycarbonyl, (Cs-Ce)- Cycloalkoxycarbonyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkoxycarbonyl, R 11 and R 12 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, (d-Ce) -alkyl, optionally substituted phenyl, heteroaryl, heterocyclyl, (C 3 -C 6 ) -cycloalkyl, (C 2 -C 6 ) - alkenyl, (C 2 -C 6) -alkynyl, (Ci-C6) alkoxy (Ci-C 6) alkyl, aryloxy (Ci-C 6) alkyl, (Ci-C 6) -haloalkyl, (Ci-C 6) haloalkoxy (Ci-C 6) alkyl, (Ci-C6) alkoxy (Ci-C 6) -haloalkyl, (Ci-C 6) haloalkoxy (Ci-C 6 ) -haloalkyl, (dC 6 ) -alkylthio (C 1 -C 6 ) -alkyl, hydroxycarbonyl, (C 1 -C 6) -alkoxycarbonyl, (Cs-Ce) -cycloalkoxycarbonyl, (C 3 -C 6) -cycloalkyl- (C 1 -C 6) alkoxycarbonyl,
Aryloxycarbonyl, Aryl-(Ci-C6)-alkoxycarbonyl, (C2-Cö)-Alkenyloxycarbonyl, (C2-C6)-Alkinyloxycarbonyl, Aminocarbonyl, (d-CeJ-Alkylaminocarbonyl, Bis[(Ci-C6)-alkyl]aminocarbonyl, (Ci-C6)-Alkyl[(Ci-C6)-Alkyl]aminocarbonyl, (Ci-C6)-Alkyl[(Ci-C6)-Alkoxy]aminocarbonyl, (C2-C6)-Alkenylaminocarbonyl, (Cs-CeJ-Cycloalkylaminocarbonyl, Arylaminocarbonyl, Aryl-(Ci-CG)- alkylaminocarbonyl stehen,
A5 für S (Schwefel), O (Sauerstoff) oder die Gruppierungen N-H, N-CH3, N-CH2CH3, N- CH(CH3)2, N-C02t-Bu, N-Aryl, N-Heteroaryl, N-Heterocyclyl steht, Aryloxycarbonyl, aryl- (C 1 -C 6) -alkoxycarbonyl, (C 2 -C 6) -alkenyloxycarbonyl, (C 2 -C 6) -alkynyloxycarbonyl, aminocarbonyl, (C 1 -C 6 -alkylaminocarbonyl, bis [(C 1 -C 6) -alkyl] aminocarbonyl, ( C 1 -C 6) -alkyl [(C 1 -C 6) -alkyl] aminocarbonyl, (C 1 -C 6) -alkyl [(C 1 -C 6) -alkoxy] aminocarbonyl, (C 2 -C 6) -alkenylaminocarbonyl, (C 1 -C 12 -cycloalkylaminocarbonyl, Arylaminocarbonyl, aryl- (Ci-CG) -alkylaminocarbonyl, A 5 for S (sulfur), O (oxygen) or the groupings NH, N-CH 3 , N-CH 2 CH 3 , N-CH (CH 3 ) 2, N-CO 2 t-Bu, N-aryl, N-heteroaryl , N-heterocyclyl,
R14, R17 und R18 unabhängig voneinander für Wasserstoff, (Ci-Ce)-Alkyl, Fluor, Chlor, Brom, lod, (C3-C6)-Cycloalkyl, gegebenenfalls substituiertes Phenyl, Heteroaryl, Heterocyclyl, (C2-C6)-Alkenyl, Aryl-(d-C6)-alkyl,
R 14 , R 17 and R 18 independently of one another represent hydrogen, (C 1 -C 6) -alkyl, fluorine, chlorine, bromine, iodine, (C 3 -C 6) -cycloalkyl, optionally substituted phenyl, heteroaryl, heterocyclyl, (C 2 -C 6) Alkenyl, aryl (C 1 -C 6) alkyl,
(Ci-C6)-Alkoxy-(Ci-C6)-alkoxy, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, Hydroxy, (Ci-C6)- Haloalkyl, (Ci-Cr,)-Haloalkylthio stehen oder und R17 mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls weiter substituierten 5 bis 7-gliedrigen Ring bilden, (C 1 -C 6 ) -Alkoxy- (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, hydroxy, (C 1 -C 6 ) -haloalkyl, (C 1 -C-Cr ,) - Haloalkylthio or and form R 17 with the atoms to which they are attached, a fully saturated or partially saturated, optionally further substituted 5 to 7-membered ring,
A6, A7 gleich oder verschieden sind und unabhängig voneinander für O (Sauerstoff), S (Schwefel), N-H, N-OCH3, N-CH3 oder die Gruppierung CR15R16 stehen, wobei jedoch in keinem Fall zwei N-, O- oder S-Atome benachbart sind, und wobei R15 und R16 in der Gruppierung CR15R16 jeweils gleiche oder verschiedene A 6 , A 7 are the same or different and independently of one another are O (oxygen), S (sulfur), NH, N-OCH 3, N-CH 3 or the group CR 15 R 16 , although in each case two N-, O or S atoms are adjacent, and wherein R 15 and R 16 in the group CR 15 R 16 are identical or different
Bedeutungen gemäß der nachstehenden Definition haben und Have meanings as defined below and
R15 und R16 unabhängig voneinander für Wasserstoff, Fluor, Chlor, Brom, lod, (d-Ce)- Alkyl, gegebenenfalls substituiertes Phenyl, Heteroaryl, Heterocyclyl, (Cs-Ce)- Cycloalkyl, (C2-C6)-Alkenyl, (Ci-C6)-Alkoxy, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, R 15 and R 16 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, (d-Ce) -alkyl, optionally substituted phenyl, heteroaryl, heterocyclyl, (Cs-Ce) -cycloalkyl, (C 2 -C 6 ) - Alkenyl, (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl,
(Ci-C6)-Haloalkoxy, (Ci-C6)-Haloalkyl, (Ci-C6)-Alkylthio, (Ci-C6)-Haloalkylthio, (CrC6)-Alkylthio-(Ci-C6)-alkyl, Hydroxycarbonyl, (Ci-Ce)-Alkoxycarbonyl, (C3-C6)-Cycloalkoxycarbonyl, Aryl-(CrCö)-alkoxycarbonyl, (C2-C-6)- Alkenyloxycarbonyl, Aminocarbonyl, (Ci-C6)-Alkylaminocarbonyl, Bis[(Ci-Ce)- alkyljaminocarbonyl, (Ci-Cr>)-Alkyl[(Ci-C6)-Alkyl]aminocarbonyl, (C2-C6)- Alkenylaminocarbonyl, (Cs-CeJ-Cycloalkylaminocarbonyl, Aryl-(Ci-Ce)- alkylaminocarbonyl, Amino, (Ci-Cej-Alkylamino, (Cs-CeJ-Cycloalkylamino, Bis- [(CrC6)-Alkyl]amino stehen,
R19, R20, R22 und R23 unabhängig voneinander für Wasserstoff, (Ci-Ce)-Alkyl, Fluor, Chlor, Brom, lod, (C3-Cö)-Cycloalkyl, Aryl, Heteroaryl, Heterocyclyl, (C2-Ce)- Alkenyl, Aryl-(Ci-C6)-alkyl, (CrC6)-Alkoxy, (Ci-C6)-Haloalkyl stehen, (C 1 -C 6 ) -haloalkoxy, (C 1 -C 6 ) -haloalkyl, (C 1 -C 6 ) -alkylthio, (C 1 -C 6 ) -haloalkylthio, (C 1 -C 6 ) -alkylthio (C 1 -C 6 ) -alkyl, Hydroxycarbonyl, (C 1 -C 6) -alkoxycarbonyl, (C 3 -C 6) -cycloalkoxycarbonyl, aryl- (C 1 -C 4) -alkoxycarbonyl, (C 2 -C 6) -alkenyloxycarbonyl, aminocarbonyl, (C 1 -C 6) -alkylaminocarbonyl, bis [(Ci -Ce) - alkyljaminocarbonyl, (Ci-Cr > ) alkyl [(Ci-C6) alkyl] aminocarbonyl, (C2-C6) - alkenylaminocarbonyl, (Cs-CeJ-cycloalkylaminocarbonyl, aryl- (Ci-Ce) - alkylaminocarbonyl, Amino, (C 1 -C 12 -alkylamino, (C 5 -C 12 -cycloalkylamino, bis- [(C 1 -C 6) -alkyl] -amino, R 19 , R 20 , R 22 and R 23 are each independently hydrogen, (Ci-Ce) alkyl, fluorine, chlorine, bromine, iodine, (C3-Cö) -cycloalkyl, aryl, heteroaryl, heterocyclyl, (C2-Ce ) - alkenyl, aryl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -haloalkyl,
A8 für O (Sauerstoff), S (Schwefel), N-H, N-CH3, N-OCH3 oder die Gruppierung CHR21 steht und wobei R21 in der Gruppierung CHR21 die Bedeutung gemäß der nachstehenden Definition hat, A 8 is O (oxygen), S (sulfur), NH, N-CH 3 , N-OCH 3 or the moiety CHR 21 , and wherein R 21 in the moiety CHR 21 has the meaning as defined below,
R21 für Wasserstoff, Fluor, Chlor, Brom, lod, (Ci-C6)-Alkyl, gegebenenfalls R 21 represents hydrogen, fluorine, chlorine, bromine, iodine, (C 1 -C 6) -alkyl, if appropriate
substituiertes Phenyl, Heteroaryl, Heterocyclyl, (C3-C6)-Cycloalkyl, (C2-C6)- Alkenyl, (CrC6)-Alkoxy, (Ci-C6)-Haloalkoxy, (Ci-C6)-Haloalkyl, (Ci-Cc)-Alkylthio, (d-C6)-Haloalkylthio, Hydroxycarbonyi, Aryl-(Ci-Cr>)-alkoxycarbonyl, (C2-C6)- Alkenyloxycarbonyl, Aminocarbonyl, (d-Ce^Alkylaminocarbonyl, Bis[(Ci-Ce)- alkyljaminocarbonyl, (Ci-C6)-Alkyl[(Ci-Cö)-Alkyl]aminocarbonyl, (d-Ce)- Alkyl[(CrC6)-Alkoxy]aminocarbonyl, (C2-C6)-Alkenylaminocarbonyl, (Ca-Ce)- Cycloalkylaminocarbonyl, Aryl-(CrC6)-alkylaminocarbonyl, Amino, (d-Ce)- Alkylamino, (C3-C6)-Cycloalkylamino, Bis[(d-C6)-Alkyl]amino steht, substituted phenyl, heteroaryl, heterocyclyl, (C3-C6) cycloalkyl, (C2-C6) - alkenyl, (CrC 6) alkoxy, (Ci-C 6) -haloalkoxy, (Ci-C 6) -haloalkyl, (C -cc) alkylthio, (d-C6) haloalkylthio, Hydroxycarbonyi, aryl (Ci-Cr>) -alkoxycarbonyl, (C2-C6) - alkenyloxycarbonyl, aminocarbonyl, (d-Ce ^ alkylaminocarbonyl, bis [(Ci-Ce ) - alkylaminocarbonyl, (C 1 -C 6) -alkyl [(C 1 -C 6) -alkyl] aminocarbonyl, (C 1 -C 6) -alkyl [(C 1 -C 6) -alkoxy] -aminocarbonyl, (C 2 -C 6) -alkenylaminocarbonyl, (Ca-Ce ) - cycloalkylaminocarbonyl, aryl- (C 1 -C 6) -alkylaminocarbonyl, amino, (C 1 -C 6) -alkylamino, (C 3 -C 6) -cycloalkylamino, bis [(C 1 -C 6) -alkyl] -amino,
R24, R25, R26, R28, R29 und R30 unabhängig voneinander für Wasserstoff, (Ci-Ce)-Alkyl, Fluor, Chlor, Brom, lod, (Ca-CeJ-Cycloalkyl, Aryl, Heteroaryl, Heterocyclyl, R 24 , R 25 , R 26 , R 28 , R 29 and R 30 are each independently hydrogen, (Ci-Ce) alkyl, fluorine, chlorine, bromine, iodine, (Ca-CeJ-cycloalkyl, aryl, heteroaryl, heterocyclyl .
(C2-C6)-Alkenyl, (Ci-C6)-Alkoxy, (Ci-C6)-Haloalkyl, (CrC6)-Alkylthio, (Ci-C6)- Haloalkylthio stehen, (C 2 -C 6) alkenyl, (Ci-C 6) alkoxy, (Ci-C 6) -haloalkyl, (CrC 6) alkylthio, (Ci-C 6) - haloalkylthio stand,
A9 für O (Sauerstoff), S (Schwefel), N-H, N-CH3, N-OCH3 oder die Gruppierung CHR27 steht und wobei R27 in der Gruppierung CHR27 die Bedeutung gemäß der nachstehenden Definition hat und A 9 is O (oxygen), S (sulfur), NH, N-CH 3 , N -OCH 3 or the moiety CHR 27 and wherein R 27 in the moiety CHR 27 has the meaning as defined below and
R27 für Wasserstoff, Fluor, Chlor, Brom, lod, (Ci-Ce)- Alkyl, gegebenenfalls R 27 is hydrogen, fluorine, chlorine, bromine, iodine, (Ci-Ce) - alkyl, optionally
substituiertes Phenyl, Heteroaryl, Heterocyclyl, (C3-Ce>)-Cycloalkyl, (C2-C6)- Alkenyl, (Ci-Co)-Alkoxy, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, (CrC6)-Haloalkoxy, substituted phenyl, heteroaryl, heterocyclyl, (C 3 -C 12) -cycloalkyl, (C 2 -C 6 ) -alkenyl, (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (CrC 6 ) haloalkoxy,
(Ci-C6)-Haloalkyl, (Ci-C6)-Alkylthio, (Ci-C6)-Haloalkylthio, Hydroxycarbonyi, (d-Cc -Alkoxycarbonyl, (C3-C6)-Cycloalkoxycarbonyl, Aryl-(Ci-Ce)- alkoxycarbonyl, Aminocarbonyl, (Ci-CeJ-Alkylaminocarbonyl, Bis[(Ci-Ce)- alkyljaminocarbonyl, (C3-C6)-Cycloalkylaminocarbonyl, Aryl-(Ci-C6)-
alkylaminocarbonyl, Amino, (Ci-C-6)-Alkylamino, (C3-C-6)-Cycloalkylamino, Bis[(Ci-C6)-Alkyl]amino steht. (C 1 -C 6 ) -haloalkyl, (C 1 -C 6 ) -alkylthio, (C 1 -C 6 ) -haloalkylthio, hydroxycarbonyi, (C 1 -C 6 -alkoxycarbonyl, (C 3 -C 6) -cycloalkoxycarbonyl, aryl- Ce) alkoxycarbonyl, aminocarbonyl, (Ci-CeJ-alkylaminocarbonyl, bis [(Ci-Ce) - alkyljaminocarbonyl, (C 3 -C 6) -cycloalkylaminocarbonyl, aryl- (Ci-C6) - alkylaminocarbonyl, amino, (C 1 -C 6) -alkylamino, (C 3 -C 6) -cycloalkylamino, bis [(C 1 -C 6 ) -alkyl] -amino.
Im Speziellen bevorzugt ist die erfindungsgemäße Verwendung von Verbindungen der allgemeinen Formel (I), die durch die Formeln (la) bis (lo) beschrieben werden, Especially preferred is the use according to the invention of compounds of the general formula (I) which are described by the formulas (Ia) to (Io)
worin
[X-Y] für die Gruppierung wherein [XY] for the grouping
[x-YT steht, [x-YT stands,
Q für die Gruppierungen Q-1 bis Q-6 Q for the groupings Q-1 to Q-6
steht, wobei R7, R8, R9, R10, R11, R12, R13, R14, R17, R 8, R19, R20, R22, R23, R24, R25, R26, R28, R29 und R30 und A1 bis A9 jeweils die Bedeutung gemäß der nachstehenden Definitionen haben und wobei der Pfeil für eine Bindung zur jeweiligen Gruppierung C-R6 in den vorgenannten Formeln (la) bis (lo) steht, where R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 17 , R 8 , R 19 , R 20 , R 22 , R 23 , R 24 , R 25 , R 26 , R 28 , R 29 and R 30 and A 1 to A 9 each have the meaning according to the definitions below and wherein the arrow for a bond to the respective group CR 6 in the aforementioned formulas (la) to (lo) .
R5 für Hydroxy, (Ci-Ce)-Alkoxy, Aryloxy, (C-3-C6)-Cycioalkyloxy, (C2-Cc,)-Alkenyloxy, (C2-C6)-Alkenyl-(Ci-C6)-alkyloxy, (Ci-C6)-Alkoxy-(Ci-C6)-alkyloxy, (Ci-C6)- Alkylcarbonyloxy, Arylcarbonyloxy, Heteroarylcarbonyloxy, (Ca-Ce)- Cycloalkylcarbonyloxy, (d-Cc -Alkoxycarbonyloxy, (C2-Ce)- Alkenyloxycarbonyloxy, Aryloxy-(Ci-Cö)-alkyloxy, Aryl-(Ci-Ce)-alkyloxy, (Ci-Ce)- Alkoxy-(Ci-C6)-alkoxy-(Ci-C6)-alkyloxy, (Ci-C6)-Alkylthio-(Ci-C6)-alkyloxy, Tris[(Ci-C6)-alkyl]silyloxy, (Ci-C6)-Alkyl-Bis[(Ci-C6)-alkyl]silyloxy, (CrC6)-Alkyl- bis(Aryl)silyloxy, Aryl-bis[(d-C6)-alkyl]silyloxy, Cycloalkyl-bis[(Ci-C6)- alkyljsilyloxy, Halo-bis[(Ci-C6)-alkyl]silyloxy, Tris[(Ci-C6)-alkyl]silyl-(Ci-C6)- alkoxy-(d-C6)-alkyloxy, steht,
für Nitro, Amino, Hydroxy, Hydrothio, Thiocyanato, Isothiocyanato, Fluor, Chlor, Brom, lod, (d-Ce)-Alkyl, (C3-C6)-Cycloalkyl, (C2-C6)-Alkenyl, (C4-C6)- Cycloalkenyl, (C2-C6)-Alkinyl, Aryl-(C2-C6)-alkinyl, Tris[(Ci-C6)-alkyl]silyl-(C2-C6)- alkinyl, Aryl, Aryl-(CrC6)-alkyl, Aryl-(Ci-C6)-alkoxy, Heteroaryl, (d-C6)- Haloalkyl, (C3-C6)-Halocycloalkyl, (C2-C6)-Haloalkenyl, (Ci-Ce)-Alkoxy, (Ci-C6)- Haloalkoxy, Aryloxy, Heteroaryloxy, (C3-Ce)-Cycloalkyloxy, (Ca-CeJ-Cycloalkyl- (Ci-C6)-alkoxy, (C2-C6)- (C2-C6)-Alkenyloxy, (C2-C6)-Alkinyl-(C2-C6)-alkyloxy, Hydroxy-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, Aryloxy-(Ci-C6)-alkyl, Heteroaryloxy-(Ci-C6)-alkyl, (Ci-Ce)-Alkylthio, (Ci-C6)-Haloalkylthio, (Ci-Ce)- Alkoxycarbonyl-(Ci-Cc>)-alkylthio, Arylthio, (Ca-CeJ-Cycloalkylthio, Heteroarylthio, (Ci-C6)-Alkylthio-(Ci-C6)-alkyl, (Ci-C6)-Alkylamino, Bis[(Ci-C6)-alkyl]amino, (C2-C6)-Alkenylamino, (C3-Cr,)-Cycloalkylamino, (Ci-C6)-Alkylcarbonylamino, (C3-C6)-Cycloalkylcarbonylamino, Arylcarbonylamino, Heteroarylcarbonylamino, Formylamino, (Ci-Cr -Haloalkylcarbonylamino,
R 5 is hydroxy, (C 1 -C 6) -alkoxy, aryloxy, (C 3 -C 6 ) -cycloalkoxy, (C 2 -C 6 ) -alkenyloxy, (C 2 -C 6 ) -alkenyl- (C 1 -C 6 ) - alkyloxy, (C 1 -C 6 ) alkoxy- (C 1 -C 6 ) alkyloxy, (C 1 -C 6 ) -alkylcarbonyloxy, arylcarbonyloxy, heteroarylcarbonyloxy, (Ca-Ce) -cycloalkylcarbonyloxy, (C 1 -C 6 -alkoxycarbonyloxy, (C 2 -C 4 ) -alkoxy) -Ce) - alkenyloxycarbonyloxy, aryloxy- (C 1 -C 6 ) -alkyloxy, aryl- (C 1 -C 6 ) -alkyloxy, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) - alkyloxy, (C 1 -C 6 ) -alkylthio (C 1 -C 6 ) -alkyloxy, tris [(C 1 -C 6 ) -alkyl] silyloxy, (C 1 -C 6 ) -alkyl-bis [(C 1 -C 6 ) - alkyl] silyloxy, (C 1 -C 6 ) alkyl bis (aryl) silyloxy, aryl bis [(C 1 -C 6) alkyl] silyloxy, cycloalkyl bis [(C 1 -C 6 ) alkyl] ssilyloxy, halo bis [(ci) C 6 ) -alkyl] silyloxy, tris [(C 1 -C 6 ) -alkyl] silyl- (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyloxy, for nitro, amino, hydroxy, hydrothio, thiocyanato, isothiocyanato, fluorine, chlorine, bromine, iodine, (d-Ce) -alkyl, (C 3 -C 6 ) -cycloalkyl, (C 2 -C 6 ) -alkenyl, ( C 4 -C 6) - cycloalkenyl, (C 2 -C 6) alkynyl, aryl (C2-C6) -alkynyl, tris [(Ci-C6) alkyl] silyl (C2-C6) - alkynyl, aryl, aryl (CrC 6) alkyl, aryl (Ci-C 6) alkoxy, heteroaryl, (dC 6) - haloalkyl, (C 3 -C 6) halocycloalkyl, (C 2 -C 6) Haloalkenyl, (Ci-Ce) alkoxy, (Ci-C 6 ) - haloalkoxy, aryloxy, heteroaryloxy, (C3-Ce) -cycloalkyloxy, (Ca-CeJ-cycloalkyl- (Ci-C 6 ) -alkoxy, (C 2 -C 6) - (C 2 -C 6) alkenyloxy, (C2-C6) alkynyl (C 2 -C 6) alkyloxy, hydroxy (Ci-C 6) alkyl, (Ci-C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, aryloxy- (C 1 -C 6 ) -alkyl, heteroaryloxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylthio, (C 1 -C 6 ) haloalkylthio, (Ci-Ce) - alkoxycarbonyl (Ci-Cc>) alkylthio, arylthio, (Ca-CeJ-cycloalkylthio, heteroarylthio, (Ci-C6) alkylthio (Ci-C6) alkyl, ( C 1 -C 6 ) -alkylamino, bis [(C 1 -C 6 ) -alkyl] -amino, (C 2 -C 6 ) -alkenylamino, (C 3 -C 8) -cycloalkylamino, (C 1 -C 4) -alkylamino, C 6) -alkylcarbonylamino, (C 3 -C 6) -cycloalkylcarbonylamino, arylcarbonylamino, heteroarylcarbonylamino, formylamino, (C 1 -C 6 -haloalkylcarbonylamino,
(Ci-Cr -Alkylaminocarbonylamino, (Ci-Cc,)-Alkyl[(Ci-C6)- Alkyl]aminocarbonylamino, (Ci-C6)-Alkylsulfonylamino, (Ca-Ce)- Cycloalkylsulfonylamino, Arylsulfonylamino, Hetarylsulfonylamino, Sulfonyl- (Ci-Cr,)-haloalkylamino, Amino-(Ci-C6)-alkylsulfonyl, Amino-(Ci-Cr,)- haloalkylsulfonyl, (Ci-C6)-Alkylaminosulfonyl, Bis[(Ci-C6)-alkyl]aminosulfonyl, (C3-C6)-Cycloalkylaminosulfonyl, (CrCc -Haloalkylaminosulfonyl, (Ci-Cr alkylaminocarbonylamino, (Ci-Cc,) - alkyl [(Ci-C6) - alkyl] aminocarbonylamino, (Ci-C6) alkylsulfonylamino, (Ca-Ce) - Cycloalkylsulfonylamino, Arylsulfonylamino, Hetarylsulfonylamino, sulfonyl (Ci -Cr,) - haloalkylamino, amino- (Ci-C6) -alkylsulfonyl, amino- (Ci-Cr,) - haloalkylsulfonyl, (Ci-C6) -alkylaminosulfonyl, bis [(Ci-C6) -alkyl] aminosulfonyl, (C3 -C 6) -cycloalkylaminosulfonyl, (C 1 -C 6 -haloalkylaminosulfonyl,
Heteroarylaminosulfonyl, Arylaminosulfonyl, Aminosulfonyl, Aryl-(Ci-C6)- alkylaminosulfonyl, (Ci-CeJ-Alkylsulfonyl, (Ca-CeJ-Cycloalkylsulfonyl, Heteroarylaminosulfonyl, arylaminosulfonyl, aminosulfonyl, aryl- (Ci-C6) -alkylaminosulfonyl, (Ci-CeJ-alkylsulfonyl, (Ca-CeJ-Cycloalkylsulfonyl,
Arylsulfonyl, (CrC6)-Alkylsulfinyl, (C3-C6)-Cycloalkylsulfinyl, Arylsulfinyl, N,S- Bis[(Ci-C6)-alkyl]sulfonimidoyl, S-(Ci-C6)-Alkylsulfonimidoyl, (Ci-C6)- Alkylsulfonylaminocarbonyl, (Ca-Ce Cycloalkylsulfonylaminocarbonyl, Aryl- (Ci-C6)-alkylcarbonylamino, (C3-C6)-Cycloalkyl-(Ci-C6)-alkylcarbonylamino, Heteroarylcarbonylamino, (Ci-C6)-Alkoxy-(Ci-C6)-alkylcarbonylamino, Hydroxy- (Ci-C6)-alkylcarbonylamino, (Ci-C6)-Alkoxycarbonylamino-(Ci-C6)- alkyicarbonylamino, Cyano, Cyano-(Ci-C6)-alkyl, Hydroxycarbonyl, (d-Ce)- Alkoxycarbonyl, (Ca-CeJ-Cycloalkoxycarbonyl, (C3-C6)-Cycloalkyl-(Ci-C6)- alkoxycarbonyl, Aryloxycarbonyl, Aryl-(d-C6)-alkoxycarbonyl, (d-Ce)- Alkenyloxycarbonyl, (C2-C6)-Alkinyloxycarbonyl, (Ci-CeJ-Haloalkyloxycarbonyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkoxycarbonyl, (C2-C6)-Alkenyloxy-(Ci-C6)-
alkoxycarbonyl, (Ci-C6)-Alkylamino-(Ci-C-6)-alkoxycarbonyl, Tris[(Ci-C-6)- alkyl]silyloxy-(CrC6)-alkoxycarbonyl, Bis[(Ci-C6)-Alkyl]amino-(Ci-C6)- alkoxycarbonyl, (Ci-C6)-Alkyl[(Ci-C6)-alkyl]amino-(CrC6)-alkoxycarbonyl, Cyano-(d-C6)-alkoxycarbonyl, Heterocyclyl-N-(CrC6)-alkoxycarbonyl, Arylsulfonyl, (CrC 6) alkylsulfinyl, (C 3 -C 6) cycloalkylsulfinyl, arylsulfinyl, N, S, bis [(Ci-C6) alkyl] sulfonimidoyl, S- (Ci-C 6) -Alkylsulfonimidoyl, ( C 1 -C 6) -alkylsulfonylaminocarbonyl, (C 1 -C 6 -cycloalkylsulfonylaminocarbonyl, aryl- (C 1 -C 6) -alkylcarbonylamino, (C 3 -C 6) -cycloalkyl- (C 1 -C 6) -alkylcarbonylamino, heteroarylcarbonylamino, (C 1 -C 6) -alkoxy) (C 1 -C 6) -alkylcarbonylamino, hydroxy- (C 1 -C 6) -alkylcarbonylamino, (C 1 -C 6) -alkoxycarbonylamino- (C 1 -C 6) -alkylcarbonylamino, cyano, cyano- (C 1 -C 6) -alkyl, hydroxycarbonyl, (i.e. -Ce) - alkoxycarbonyl, (Ca-CeJ-cycloalkoxycarbonyl, (C3-C6) -cycloalkyl- (Ci-C6) -alkoxycarbonyl, aryloxycarbonyl, aryl- (d-C6) -alkoxycarbonyl, (d-Ce) -alkenyloxycarbonyl, ( C 2 -C 6 -alkynyloxycarbonyl, (C 1 -C 6 -haloalkyloxycarbonyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkoxycarbonyl, (C 2 -C 6 ) -alkenyloxy- (C 1 -C 6 ) - alkoxycarbonyl, (C 1 -C 6) -alkylamino- (C 1 -C 6) -alkoxycarbonyl, tris [(C 1 -C 6) -alkyl] silyloxy- (C 1 -C 6) -alkoxycarbonyl, bis [(C 1 -C 6) -alkyl] amino (C 1 -C 6) alkoxycarbonyl, (C 1 -C 6) alkyl [(C 1 -C 6) alkyl] amino (C 1 -C 6) alkoxycarbonyl, cyano (C 1 -C 6) alkoxycarbonyl, heterocyclyl N- (CrC 6 ) -alkoxycarbonyl
Heteroaryloxycarbonyl, Heteroaryl-(Ci-C6)-alkoxycarbonyl, HeterocyclyKCrCe)- alkoxycarbonyl, Heterocyclyloxycarbonyl, (C2-C6)-Alkenyl-(d-C6)- alkoxycarbonyl, (C2-C6)-Alkinyl-(CrC6)-alkoxycarbonyl, Aryl-(C2-Ce)- alkinyloxycarbonyl, Aryl-(C2-C6)-alkenyloxycarbonyl, Aminocarbonyl, (Ci-Ce)- Alkylaminocarbonyl, Bis[(Ci-Cö)-alkyl]aminocarbonyl, (Ci-C6)-Alkyl[(Ci-C6)- Alkyl]aminocarbonyl, (Ci-C6)-Alkyl[(Ci-C6)-Alkoxy]aminocarbonyl, (C2-Ce)- Alkenylaminocarbonyl, (C3-Cö)-Cycloalkylaminocarbonyl, Arylaminocarbonyl, Aryl-(Ci-C6)-alkylaminocarbonyl, Heteroaryl-(CrC6)-alkylaminocarbonyl, Cyano- (Ci-C6)-alkylaminocarbonyl, (CrC6)-Haloalkylaminocarbonyl, (C2-Ce)-Alkinyl- (CrCeJ-alkylaminocarbonyl, (CrC6)-Alkoxycarbonylaminocarbonyl, Aryl-(Ci-C-6)- alkoxycarbonylaminocarbonyl, Hydroxycarbonyl-(Ci-C6)-alkyl, (Ci-Ce)- Alkoxycarbonyl-(d-C6)-alkyl, (C3-C6)-Cycloalkoxycarbonyl-(CrC6)-alkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkoxycarbonyl-(Ci-C6)-alkyl, (C2-C6)- Alkenyloxycarbonyl-(Ci-C6)-alkyl, Aryl-(Ci-C6)-alkoxycarbonyl-(Ci-C6)-alkyl, (Ci-C6)-Alkylaminocarbonyl-(Ci-C6)-alkyl, Aminocarbonyl-(Ci-C6)-alkyl, Heteroaryloxycarbonyl, heteroaryl- (Ci-C6) -alkoxycarbonyl, heterocyclyKCrCe) -alkoxycarbonyl, heterocyclyloxycarbonyl, (C 2 -C 6) -alkenyl- (C 1 -C 6) -alkoxycarbonyl, (C 2 -C 6) -alkynyl- (C 1 -C 6) -alkoxycarbonyl, aryl - (C 2 -C 6) - alkynyloxycarbonyl, aryl- (C 2 -C 6) -alkenyloxycarbonyl, aminocarbonyl, (C 1 -C 6) -alkylaminocarbonyl, bis [(C 1 -C 6) -alkyl] aminocarbonyl, (C 1 -C 6) -alkyl [( C 1 -C 6) -alkyl] aminocarbonyl, (C 1 -C 6) -alkyl [(C 1 -C 6) -alkoxy] aminocarbonyl, (C 2 -C 6) -alkenylaminocarbonyl, (C 3 -C 6) -cycloalkylaminocarbonyl, arylaminocarbonyl, aryl- C 6) -alkylaminocarbonyl, heteroaryl- (C 1 -C 6) -alkylaminocarbonyl, cyano- (C 1 -C 6) -alkylaminocarbonyl, (C 1 -C 6) -haloalkylaminocarbonyl, (C 2 -C 6) -alkynyl- (C 1 -C 6 -alkylaminocarbonyl, (C 1 -C 6) -alkoxycarbonylaminocarbonyl, aryl- (C 1 -C 6 -alkoxycarbonylaminocarbonyl, hydroxycarbonyl- (C 1 -C 6) -alkyl, (C 1 -C 6) -alkoxycarbonyl- (C 1 -C 6) -alkyl, (C 3 -C 6) -cycloalkoxycarbonyl- (C 1 -C 6) -alkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkoxycarbonyl- (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyloxycarbonyl- (C 1 -C 6 ) -alkyl, aryl- ( C 1 -C 6) -alkoxycarbonyl- (C 1 -C 6) -alkyl, (C 1 -C 6) -alkylaminocarbonyl- (C 1 -C 6) -alkyl, aminocarbonyl- (C 1 -C 6) -alkyl,
Bis[(Ci-C6)-alkyl]aminocarbonyl-(Ci-C6)-alkyl, (Ca-CeJ-Cycloalkylaminocarbonyl- (CrC6)-alkyl, Aryl-(Ci-C6)-alkylaminocarbonyl-(Ci-C6)-alkyl, Heteroaryl-(Ci-C6)- alkylaminocarbonyl-(CrC6)-alkyl, Cyano-(Ci-C6)-alkylaminocarbonyl-(Ci-C6)- alkyl, (Ci-C6)-Haloalkylaminocarbonyl-(Ci-C6)-alkyl, (C2-C6)-Alkinyl-(Ci-C6)- alkylaminocarbonyl-(Ci-C6)-alkyL (C3-C6)-Cycloalkyl-(Ci-C6)- alkylaminocarbonyl-(CrC6)-alkyl, (Ci-CeJ-Alkoxycarbonylaminocarbonyl- (CrCeJ-alkyl, Aryl-(Ci-C6)-alkoxycarbonylaminocarbonyl-(CrC6)-alkyl, (d-Ce)- Alkoxycarbonyl-(Ci-Cö)-alkylaminocarbonyl, Hydroxycarbonyl-(Ci-C6)- alkylaminocarbonyl, Aryl-(Ci-C6)-alkoxycarbonyl-(Ci-C6)-alkylaminocarbonyl, (Ci-C6)-Alkoxycarbony!-heterocyclyl-N-carbonyl, (Ci-Cr,)-Alkoxycarbonyl-(Ci- C6)-alkyl-heterocyclylidenaminocarbonyl, (Ci-Ce)- Alkoxycarbonyiheterocyclyliden-(Ci-C6)-alkylaminocarbonyl (Ci-Ce)- Alkoxycarbonyi-(Ci-C6)-Alkyl((Ci-Cö)-alkyl)aminocarbonyl, (Ci-Ce)- Alkoxycarbonyl-(C3-Cr>)-cycloalkylidenaminocarbonyl, Heterocyclyl-N-carbonyl,
(Ci-C6)-Alkoxy-(Ci-C6)-alkylaminocarbonyl, Aminocarbonyl-(Ci-C6)- alkylaminocarbonyl, (Ci-C6)-Alkylaminocarbonyl-(Ci-C6)-alkylaminocarbonyl, (C3-C6)-Cycloalkylaminocarbonyl-(Ci-C6)-alkylaminocarbonyl, (Ca-Ce)- Cycloalkyl-(Ci-C6)-alkylaminocarbonyl, (C3-C6)-Cycloalkyl-(CrC6)- alkylaminocarbonyl-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl-(Ci-C6)- alkylaminocarbonyl-(Ci-C6)-alkylaminocarbonyl, (C-2-C6)-Alkenyl-(Ci-C-6)- alkylaminocarbonyl, (C2-C6)-Alkenylaminocarbonyl-(CrC6)-alkyl, (C2-Cr,)- Alkenyl-(Ci-C6)-alkylaminocarbonyl-(Ci-C6)-alkyl, (Ci-C6)-Alkylcarbonyl, (C3-C6)- Cycloalkylcarbonyl, Arylcarbonyl, Formyl, Hydroxyiminomethyl, Bis [(Ci-C6) alkyl] aminocarbonyl- (Ci-C6) -alkyl, (Ca-CeJ-Cycloalkylaminocarbonyl- (CrC 6 ) -alkyl, aryl- (Ci-C 6 ) -alkylaminocarbonyl- (Ci-C 6 ) -alkyl, heteroaryl- (C 1 -C 6 ) -alkylaminocarbonyl- (C 1 -C 6 ) -alkyl, cyano- (C 1 -C 6 ) -alkylaminocarbonyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkylaminocarbonyl- (Ci C6) alkyl, (C2-C6) alkynyl (Ci-C6) - alkylaminocarbonyl (Ci-C6) alkyl (C 3 -C 6) -cycloalkyl- (Ci-C6) - alkylaminocarbonyl (C 1 -C 6) -alkyl, (C 1 -C 6 -alkoxycarbonylaminocarbonyl- (C 1 -C 6 -alkyl, aryl- (C 1 -C 6) -alkoxycarbonylaminocarbonyl- (C 1 -C 6) -alkyl, (C 1 -C 6) -alkoxycarbonyl- (C 1 -C 6) -alkylaminocarbonyl, Hydroxycarbonyl- (C 1 -C 6) -alkylaminocarbonyl, aryl- (C 1 -C 6) -alkoxycarbonyl- (C 1 -C 6) -alkylaminocarbonyl, (C 1 -C 6) -alkoxycarbony! -Heterocyclyl-N-carbonyl, (C 1 -Cr,) - Alkoxycarbonyl- (Ci- C6) -alkyl-heterocyclylidenaminocarbonyl, (Ci-Ce) - Alkoxycarbonyiheterocyclyliden- (Ci-C6) -alkylaminocarbonyl (Ci-Ce) - Alkoxycarbonyi- (Ci-C6) -Alkyl ((Ci-Cö) -alkyl ) aminocarbonyl, (C-Ce) - alkoxycarbonyl (C3-Cr>) -cycloalkylidenaminocarbon yl, heterocyclyl-N-carbonyl, (C 1 -C 6) -alkoxy- (C 1 -C 6) -alkylaminocarbonyl, aminocarbonyl- (C 1 -C 6) -alkylaminocarbonyl, (C 1 -C 6) -alkylaminocarbonyl- (C 1 -C 6) -alkylaminocarbonyl, (C 3 -C 6) -cycloalkylaminocarbonyl- (C 1 -C 6) -alkylaminocarbonyl, (Ca-Ce) -cycloalkyl- (C 1 -C 6) -alkylaminocarbonyl, (C 3 -C 6) -cycloalkyl- (C 1 -C 6) -alkylaminocarbonyl- (C 1 -C 6) -alkyl, (C 3 -C 6) ) -Cycloalkyl- (Ci-C6) -alkylaminocarbonyl- (Ci-C6) -alkylaminocarbonyl, (C-2-C6) -alkenyl- (Ci-C-6) -alkylaminocarbonyl, (C2-C6) -alkenylaminocarbonyl- (CrC6 ) alkyl, (C2-Cr,) - alkenyl, (Ci-C6) alkylaminocarbonyl (Ci-C 6) alkyl, (Ci-C 6) alkylcarbonyl, (C 3 -C 6) - cycloalkylcarbonyl, Arylcarbonyl, formyl, hydroxyiminomethyl,
Aminoiminomethyl, (Ci-C6)-Alkoxyiminomethyl, (Ci-Cc -Alkylaminoiminomethyl, Bis[(Ci-C6)-alkyl]aminoiminomethyl, (Ca-CeJ-Cycloalkoxyiminomethyl, (C3-Ce)- Cycloalkyl-(CrC6)-alkoximinomethyl, Aryloximinomethyl, Aryl-(Ci-CG)- alkoxyiminomethyl, Aryl-(Ci-C6)-alkylaminoiminomethyl, (C2-Ce)- Alkenyloxyiminomethyl, Arylaminoiminomethyl, Arylsulfonylaminoiminomethyl, Heteroaryl-(Ci-C6)-alkyl, Heterocyclyl-(Ci-C6)-alkyl, Aminoiminomethyl, (C 1 -C 6) -alkoxyiminomethyl, (C 1 -C 6 -alkylaminoiminomethyl, bis [(C 1 -C 6) -alkyl] aminoiminomethyl, (C 1 -C 12 -cycloalkoxyiminomethyl, (C 3 -C 6) -cycloalkyl- (C 1 -C 6) -alkoximinomethyl, Aryloximinomethyl, aryl- (C 1 -C 4 ) -alkoxyiminomethyl, aryl- (C 1 -C 6 ) -alkylaminoiminomethyl, (C 2 -C 6 ) -alkenyloxyiminomethyl, arylaminoiminomethyl, arylsulfonylaminoiminomethyl, heteroaryl- (C 1 -C 6 ) -alkyl, heterocyclyl- (ci) C 6 ) alkyl,
Hydroxycarbonylheterocyclyl, (Ci-C6)-Alkoxycarbonylheterocyclyl, (C2-C-6)- Alkenyloxycarbonylheterocyclyl, (C2-C6)-Alkenyl-(d-C6)- alkoxycarbonylheterocyclyl, Aryl-(Ci-C6)-alkoxycarbonylheterocyclyl, (Ca-Ce)- Cycloalkoxycarbonylheterocyclyl, (C3-C6)-Cycloalkyl-(Ci-Cr>)- alkoxycarbonylheterocyclyl, Aminocarbonylheterocyclyl, (Ci-Ce)- Alkylaminocarbonylheterocyclyl, Bis[(CrC6)-Alkyl]aminocarbonylheterocyclyl, (C3-C6)-Cycloalkylaminocarbony!heterocyclyl, Aryl-(Ci-Cr>)- alkylaminocarbonylheterocyclyi, (C2-C6)-Alkenylaminocarbonylheterocyclyl, Hydroxycarbonylheterocyclyl-(Ci-C6)-alkyl, (CrC6)-Alkoxycarbonylheterocyclyl- (Ci-C6)-alkyl, Hydroxycarbonyl-(C3-C6)-cycloalkyl-(Ci-C6)-alkyl, (Ci-C6)- Alkoxycarbonyl-(C3-C6)-cycloalkyl-(Ci-C6)-alkyl, Hydroxyaminocarbonyi, Hydroxycarbonylheterocyclyl, (C 1 -C 6) alkoxycarbonylheterocyclyl, (C 2 -C 6) alkenyloxycarbonylheterocyclyl, (C 2 -C 6) alkenyl- (C 1 -C 6) alkoxycarbonylheterocyclyl, aryl- (C 1 -C 6) alkoxycarbonylheterocyclyl, (Ca-Ce ) - Cycloalkoxycarbonylheterocyclyl, (C3-C6) -cycloalkyl- (Ci-Cr) -alkoxycarbonylheterocyclyl, aminocarbonylheterocyclyl, (Ci-Ce) -alkylaminocarbonylheterocyclyl, bis [(CrC6) -alkyl] aminocarbonylheterocyclyl, (C3-C6) -cycloalkylaminocarbonyl-heterocyclyl , aryl (Ci-Cr>) - alkylaminocarbonylheterocyclyi, (C2-C6) -Alkenylaminocarbonylheterocyclyl, Hydroxycarbonylheterocyclyl- (Ci-6) alkyl, (CRC6) -Alkoxycarbonylheterocyclyl- (Ci-C 6) alkyl, hydroxycarbonyl (C 3 -C 6) -cycloalkyl- (Ci-C6) alkyl, (Ci-C 6) - (alkoxycarbonyl C3-C6) cycloalkyl- (Ci-C6) alkyl, Hydroxyaminocarbonyi,
(Ci-C6)-Aikoxyaminocarbonyl, Aryl-(Ci-C6)-alkoxyaminocarbonyL Heterocyclyl, (Ci-Cc>)-Alkylcarbonyloxy, Arylcarbonyloxy, Heteroarylcarbonyloxy, (Cs-Ce)- Cycloalkylcarbonyloxy, (Ci-C6)-Alkoxycarbonyloxy, (C2-C6)- Alkenyloxycarbonyloxy steht, (Ci-C6) -Aikoxyaminocarbonyl, aryl- (Ci-C6) -alkoxyaminocarbonyL heterocyclyl, (Ci-Cc>) - alkylcarbonyloxy, arylcarbonyloxy, heteroarylcarbonyloxy, (Cs-Ce) - cycloalkylcarbonyloxy, (Ci-C6) -alkoxycarbonyloxy, (C2 -C6) - alkenyloxycarbonyloxy,
R7, R8 , R9 und R10 unabhängig voneinander für Wasserstoff, Fluor, Chlor, Brom, lod, Nitro, Amino, Cyano, (Ci-Cs)-Alkyl, gegebenenfalls substituiertes Phenyl, Heteroaryl, (C3-C6)-Cycloalkyl, (C4-C6)-Cycloalkenyl, (C2-C5)-Alkenyl, (C2-C5)-
Alkinyl, (C2-C5)-Alkenyl-(Ci-C5)-alkyl, (C2-C5)-Alkinyl-(Ci-C5)-alkyl, Hydroxy, (Ci-C5)-Alkoxy, (Ci-C5)-Alkoxy-(Ci-C5)-alkoxy, (Ci-C5)-Alkoxy-(Ci-C5)-alkyl, Hydroxy-(CrCr>)-alkyl, (CrC5)-Haloalkoxy, (Ci-C5)-Haloalkyl, (C2-C5)- Haloalkenyl, (C2-C5)-Haloalkinyl, (Ci-C5)-Haloalkoxy-(Ci-C5)-alkyl, (C1-C5)- Alkoxy-(CrC5)-haloalkyl, (Ci-C5)-Haloalkoxy-(Ci-C5)-haloalkyl, Hydrothio, (Ci-C5)-Alkylthio, (CrC5)-Haloalkylthio, (Ci-C5)-Alkylthio-(Ci-C5)-alkyl, (C1-C5)- Haloalkylthio-(Ci-C5)-alkyL (Ci-C5)-Alkylamino, Bis[(Ci-C5)-alkyl]amino, (C2-C5)- Alkenylamino, (Ca-CeJ-Cycloalkylamino, (Ci-CsJ-Alkylcarbonylamino, (Ca-Ce)- Cycloalkylcarbonylamino, Arylcarbonylamino, Heteroaryicarbonylamino, Formylamino, (Ci-C5)-Haloalkylcarbonylamino, (Ci-C5)-Alkoxycarbonylamino, (Ci-C5)-Alkylaminocarbonylamino, (Ci-C5)-Alkyl[(d-C5)- Alkyljaminocarbonylamino, (Ci-C5)-Alkylsulfonylamino, (Ca-Ce)- Cycloalkylsulfonylamino, Arylsulfonylamino, Hetarylsulfonylamino, Sulfonyl- (Ci-Cr>)-haloalkylamino, Amino-(CrC5)-alkylsulfonyl, Amino-(d-C5)- haloalkylsulfonyl, (Ci-C5)-Alkylaminosulfonyl, Bis[(Ci-C5)-alkyl]aminosulfonyl, (C3-C6)-Cycloalkylaminosulfonyl, (CrCr^-Haloalkylaminosulfonyl, R 7 , R 8 , R 9 and R 10 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, nitro, amino, cyano, (C 1 -C 8) -alkyl, optionally substituted phenyl, heteroaryl, (C 3 -C 6 ) -Cycloalkyl, (C 4 -C 6 ) -cycloalkenyl, (C 2 -C 5 ) -alkenyl, (C 2 -C 5 ) - Alkynyl, (C 2 -C 5 ) -alkenyl- (C 1 -C 5 ) -alkyl, (C 2 -C 5 ) -alkynyl- (C 1 -C 5 ) -alkyl, hydroxy, (C 1 -C 5 ) -alkoxy, ( Ci-C 5 ) -alkoxy- (Ci-C 5 ) -alkoxy, (Ci-C 5 ) -alkoxy- (Ci-C 5 ) -alkyl, hydroxy (CrCr > ) -alkyl, (CrC 5 ) -haloalkoxy , (C 1 -C 5 ) -haloalkyl, (C 2 -C 5 ) -haloalkenyl, (C 2 -C 5 ) -haloalkynyl, (C 1 -C 5 ) -haloalkoxy- (C 1 -C 5 ) -alkyl, (C 1 -C 5 ) - Alkoxy- (CrC 5 ) -haloalkyl, (Ci-C 5 ) -haloalkoxy- (Ci-C 5 ) -haloalkyl, hydrothio, (Ci-C 5 ) -alkylthio, (CrC 5 ) haloalkylthio, (Ci-C 5 ) -alkylthio (C 1 -C 5 ) -alkyl, (C 1 -C 5 ) -haloalkylthio (C 1 -C 5 ) -alkyl (C 1 -C 5 ) -alkylamino, bis [(C 1 -C 5 ) -alkyl] amino, (C 2 -C 5) -alkenylamino, (C 1 -C 6 -cycloalkylamino, (C 1 -C 6 -alkylcarbonylamino, (C 1 -C 6) -cycloalkylcarbonylamino, arylcarbonylamino, heteroaryicarbonylamino, formylamino, (C 1 -C 5) -haloalkylcarbonylamino, (C 1 -C 5) ) Alkoxycarbonylamino, (C 1 -C 5) -alkylaminocarbonylamino, (C 1 -C 5) -alkyl [(C 1 -C 5) -alkyl] aminocarbonylamino, (C 1 -C 5) -alkylsulfonylamino, (Ca-Ce) -cycloalkylsulfonylamino, arylsulfonylamino, hetarylsulfonylamino, sulf onyl- (Ci-Cr>) -haloalkylamino, amino (CRC5) alkylsulfonyl, amino (d-C5) - haloalkylsulfonyl, (Ci-C5) alkylaminosulfonyl, bis [(Ci-C5) alkyl] aminosulfonyl, ( C 3 -C 6) -cycloalkylaminosulfonyl, (C 1 -C 9 -haloalkylaminosulfonyl,
Heteroarylaminosulfonyl, Arylaminosulfonyl, Aryl-(Ci-C5)-alkylaminosulfonyl, (Ci-C5)-Alkylsulfonyl, (C3-C6)-Cycloalkylsulfonyl, Arylsulfonyl, Hydroxycarbonyl, (Ci-C5)-Alkoxycarbonyl, (Ca-Ce Cycloalkoxycarbonyl, (C3-C6)-Cycloalkyl- (Ci-C5)-alkoxycarbonyl, Aryloxycarbonyl, Aryl-(Ci-C5)-alkoxycarbonyl, (C2-C5)- Alkenyloxycarbonyl, (C2-C5)-Alkinyloxycarbonyl, Aminocarbonyl, (C1-C5)- Alkylaminocarbonyl, Bis[(CrC5)-alkyl]aminocarbonyl, (Ci-C5)-Alkyl[(d-C5)- Alkyljaminocarbonyl, (Ci-C5)-Alkyl[(CrC5)-Alkoxy]aminocarbonyl, (C2-C5)- Alkenylaminocarbonyl, (Ca-CeJ-Cycloalkylaminocarbonyl, Arylaminocarbonyl, Aryl-(Ci-C5)-alkylaminocarbonyl stehen, Heteroarylaminosulfonyl, arylaminosulfonyl, aryl- (Ci-C5) -alkylaminosulfonyl, (Ci-C5) -alkylsulfonyl, (C3-C6) -cycloalkylsulfonyl, arylsulfonyl, hydroxycarbonyl, (Ci-C5) -alkoxycarbonyl, (Ca-Ce cycloalkoxycarbonyl, (C3 -C 6) -cycloalkyl- (C 1 -C 5) -alkoxycarbonyl, aryloxycarbonyl, aryl- (C 1 -C 5) -alkoxycarbonyl, (C 2 -C 5) -alkenyloxycarbonyl, (C 2 -C 5) -alkynyloxycarbonyl, aminocarbonyl, (C 1 -C 5) - Alkylaminocarbonyl, bis [(C 1 -C 5) -alkyl] aminocarbonyl, (C 1 -C 5) -alkyl [(C 1 -C 5) -alkyl] aminocarbonyl, (C 1 -C 5) -alkyl [(C 1 -C 5) -alkoxy] -aminocarbonyl, (C 2 -C 5) - Alkenylaminocarbonyl, (Ca-CeJ-cycloalkylaminocarbonyl, arylaminocarbonyl, aryl- (Ci-C5) -alkylaminocarbonyl,
A2, A3 und A4 gleich oder verschieden sind und unabhängig voneinander für N (Stickstoff) oder die Gruppierungen C-H, C-CH3, C-F, C-Cl, C-Br, C-l, C-OCF3, C-OCH3, C-CF3, C-CO2H, C-CO2CH3 stehen, wobei jedoch in keinem Fall mehr als zwei N-Atome benachbart sind, und R12 unabhängig voneinander für Wasserstoff, Fluor, Chlor, Brom, lod, (C1-C5)- Alkyl, gegebenenfalls substituiertes Phenyl, Heteroaryl, Heterocyclyl, (Cs-Ce)- Cycloalkyl, (C2-C5)-Alkenyl, (C2-C5)-Alkinyl, (CrC5)-Haloalkyl, (C1-C5)-
Haloalkoxy-(Ci-C5)-alkyl , (Ci-C5)-Alkylthio-(Ci-C5)-alkyl, Hydroxycarbonyl, (CrC5)-Alkoxycarbonyl, (C3-Cö)-Cycloalkoxycarbonyl, (C3-Cc>)-Cycloalkyl- (Ci-Cr>)-alkoxycarbonyl, Aryloxycarbonyl, Aryl-(Ci-C5)-alkoxycarbonyl, (C2-C5)- Alkenyloxycarbonyl, (C2-C5)-Alkinyloxycarbonyl, Aminocarbonyl, (C1-C5)- Alkylaminocarbonyl, Bis[(CrC5)-alkyl]aminocarbonyl, (Ci-C5)-Alkyl[(Ci-C5)- Alkyl]aminocarbonyl, (Ci-Cr,)-Alkyl[(Ci-C5)-Alkoxy]aminocarbonyl, (C2-C5)- Alkenylaminocarbonyl, (Ca-CeJ-Cycloalkylaminocarbonyl, Arylaminocarbonyl, Aryl-(Ci-C5)-alkylaminocarbonyl stehen, A 2 , A 3 and A 4 are the same or different and are each independently N (nitrogen) or the groupings CH, C-CH 3, CF, C-Cl, C-Br, Cl, C-OCF 3, C-OCH 3, C -CF 3, C-CO2H, C-CO2CH3 are, but in no case more than two N atoms are adjacent, and R 12 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, (C1-C5) - alkyl , optionally substituted phenyl, heteroaryl, heterocyclyl, (Cs-Ce) - cycloalkyl, (C 2 -C 5) alkenyl, (C 2 -C 5) alkynyl, (-C 5) haloalkyl, (C1-C5) - Haloalkoxy (Ci-C 5) alkyl, (Ci-C5) alkylthio (Ci-C5) alkyl, hydroxycarbonyl, (CRC5) alkoxycarbonyl, (C3-COE) -cycloalkoxycarbonyl, (C3-Cc>) cycloalkyl (Ci-Cr>) -alkoxycarbonyl, aryloxycarbonyl, aryl (Ci-C5) -alkoxycarbonyl, (C2-C5) - alkenyloxycarbonyl, (C2-C5) -alkynyloxycarbonyl, aminocarbonyl, (C1-C5) - alkylaminocarbonyl, Bis [(C 1 -C 5) -alkyl] aminocarbonyl, (C 1 -C 5) -alkyl [(C 1 -C 5) -alkyl] aminocarbonyl, (C 1 -C 18) -alkyl [(C 1 -C 5) -alkoxy] -aminocarbonyl, (C 2 -C 5) -alkyl C5) - alkenylaminocarbonyl, (Ca-CeJ-cycloalkylaminocarbonyl, arylaminocarbonyl, aryl- (Ci-C5) -alkylaminocarbonyl,
A5 für S (Schwefel), O (Sauerstoff) oder die Gruppierungen N-H, N-CH3, N-CH2CH3, N- CH(CH3)2, N-C02t-Bu, N-Aryl, N-Heteroaryl, N-Heterocyclyl steht, A 5 represents S (sulfur), O (oxygen) or the groupings NH, N-CH 3 , N-CH 2 CH 3 , N-CH (CH 3 ) 2 , N-CO 2 t-Bu, N-aryl, N-heteroaryl, N-heterocyclyl is
R13, R14, R17 und R18 unabhängig voneinander für Wasserstoff, (CrCr,)-Alkyl, Fluor, Chlor, Brom, lod, (C3-C6)-Cycloalkyl, gegebenenfalls substituiertes Phenyl, Heteroaryl, Heterocyclyl, (C2-C5)-Alkenyl, Aryl-(Ci-C5)-alkyl, (Ci-C5)-Alkoxy, (Ci-C5)-Alkoxy-(Ci-C5)-alkoxy, (Ci-C5)-Alkoxy-(Ci-C5)-alkyl, Hydroxy, (C1-C5)- Haloalkyl, (Ci-C-5)-Haloalkylthio stehen oder R 13 , R 14 , R 17 and R 18 are each independently hydrogen, (CrCr,) - alkyl, fluorine, chlorine, bromine, iodine, (C 3 -C 6) -cycloalkyl, optionally substituted phenyl, heteroaryl, heterocyclyl, (C 2 -C 5 ) -alkenyl, aryl- (Ci-C 5 ) -alkyl, (Ci-C 5 ) -alkoxy, (Ci-C 5 ) -Alkoxy- (Ci-C 5 ) -alkoxy, (Ci-C 5 ) Alkoxy- (C 1 -C 5 ) -alkyl, hydroxy, (C 1 -C 5 ) -haloalkyl, (C 1 -C-5) -haloalkylthio or
R13 und R17 mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls weiter substituierten 5 bis 7-gliedrigen Ring bilden, R 13 and R 17 with the atoms to which they are attached form a completely saturated or partially saturated, optionally further substituted 5 to 7-membered ring,
A6, A7 gleich oder verschieden sind und unabhängig voneinander für O (Sauerstoff), S (Schwefel), N-H, N-OCH3, N-CH3 oder die Gruppierung CR15R16 stehen, wobei jedoch in keinem Fall zwei N-, O- oder S-Atome benachbart sind, und wobei R15 und R16 in der Gruppierung CR15R16 jeweils gleiche oder verschiedene A 6 , A 7 are identical or different and independently of one another are O (oxygen), S (sulfur), NH, N-OCH 3, N-CH 3 or the group CR 15 R 16 , but in no case are two N , O or S atoms are adjacent, and wherein R 15 and R 16 in the group CR 15 R 16 are each the same or different
Bedeutungen gemäß der nachstehenden Definition haben und Have meanings as defined below and
R15 und R16 unabhängig voneinander für Wasserstoff, Fluor, Chlor, Brom, lod, (C1-C5)- Alkyl, gegebenenfalls substituiertes Phenyl, Heteroaryl, Heterocyclyl, (C3-C6)- Cycloalkyl, (C2-C5)-Alkenyl, (Ci-C5)-Alkoxy, (Ci-C5)-Alkoxy-(Ci-C5)-alkyl, (CrC5)-Haloalkoxy, (Ci-C5)-Haloalkyl, (Ci-C5)-Alkylthio, (Ci-C5)-Haloalkylthio, (Ci-C5)-Alkylthio-(Ci-C5)-alkyl, Hydroxycarbonyl, (Ci-C5)-Alkoxycarbonyl, (C3-Cr>)-Cycloalkoxycarbonyl, Aryl-(Ci-C5)-alkoxycarbonyl, (C2-C5)-
Alkenyloxycarbonyl, Aminocarbonyl, (Ci-C5)-Alkylaminocarbonyl, Bis[(Ci-Cs)- alkyljaminocarbonyl, (Ci-Cr,)-Alkyl[(Ci-C5)-Alkyl]aminocarbonyl, (C2-C5)- Alkenylaminocarbonyl, (Ca-CeJ-Cycloalkylaminocarbonyl, Aryl-(d-C5)- alkylaminocarbonyl, Amino, (d-Cs Alkylamino, (Ca-CeJ-Cycioalkylamino, Bis- [(Ci-C5)-Alkyl]amino stehen, R 15 and R 16 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, (C 1 -C 5 ) -alkyl, optionally substituted phenyl, heteroaryl, heterocyclyl, (C 3 -C 6) -cycloalkyl, (C 2 -C 5 ) - alkenyl, (Ci-C 5) alkoxy, (Ci-C 5) alkoxy (Ci-C 5) alkyl, (CrC 5) haloalkoxy, (Ci-C5) haloalkyl, (Ci-C 5 ) alkylthio, (Ci-C 5) haloalkylthio, (Ci-C5) alkylthio (Ci-C5) alkyl, hydroxycarbonyl, (Ci-C5) alkoxycarbonyl, (C3-Cr>) -cycloalkoxycarbonyl, aryl (C 1 -C 5) -alkoxycarbonyl, (C 2 -C 5) - Alkenyloxycarbonyl, aminocarbonyl, (Ci-C5) -alkylaminocarbonyl, bis [(Ci-Cs) - alkyljaminocarbonyl, (Ci-Cr,) - alkyl [(Ci-C5) -alkyl] aminocarbonyl, (C2-C5) - alkenylaminocarbonyl, ( Ca-CeJ-cycloalkylaminocarbonyl, aryl- (C 1 -C 5) -alkylaminocarbonyl, amino, (C 1 -C -alkylamino, (C 1 -C 6 -cycloalkylamino, bis- [(C 1 -C 5) -alkyl] -amino,
R19, R20, R22 und R23 unabhängig voneinander für Wasserstoff, (Ci-Cr>)-Alkyl, Fluor, Chlor, Brom, lod, (C3-C6)-Cycloalkyl, gegebenenfalls substituiertes Phenyl, Heteroaryl, Heterocyclyl, (C2-C5)-Alkenyl, Aryl-(Ci-Cr.)-alkyl, (Ci-C5)-Alkoxy, (Ci-C5)-Haloalkyl stehen, R 19, R 20, R 22 and R 23 are independently hydrogen, (Ci-Cr>) alkyl, fluoro, chloro, bromo, iodo, (C3-C6) -cycloalkyl, optionally substituted phenyl, heteroaryl, heterocyclyl, ( C 2 -C 5) alkenyl, aryl (Ci-Cr.) - alkyl, (Ci-C 5) alkoxy, (Ci-C 5) -haloalkyl stand,
A8 für O (Sauerstoff), S (Schwefel), N-H, N-CH3, N-OCH3 oder die Gruppierung CHR21 steht und wobei R21 in der Gruppierung CHR21 die Bedeutung gemäß der nachstehenden Definition hat, A 8 is O (oxygen), S (sulfur), NH, N-CH 3 , N-OCH 3 or the moiety CHR 21 , and wherein R 21 in the moiety CHR 21 has the meaning as defined below,
R21 für Wasserstoff, Fluor, Chlor, Brom, lod, (Ci-Ce)-Alkyl, gegebenenfalls R 21 is hydrogen, fluorine, chlorine, bromine, iodine, (C 1 -C 6) -alkyl, if appropriate
substituiertes Phenyl, Heteroaryl, Heterocyclyl, (C3-Cc>)-Cycloalkyl, (C -CÖ)- Alkenyl, (Ci-Ce)-Alkoxy, (Ci-C6)-Haloalkoxy, (Ci-C6)-Haloalkyl, (Ci-C6)-Alkylthio, (Ci-C6)-Haloalkylthio, Hydroxycarbonyl, Aryl-(Ci-C6)-alkoxycarbonyl, (C2-C6)- Alkenyloxycarbonyl, Aminocarbonyl, (Ci-CeJ-Alkylaminocarbonyl, Bis[(Ci-Ce)- alkyljaminocarbonyl, (CrC6)-Alkyl[(Ci-C6)-Alkyl]aminocarbonyl, (d-Ce)- Alkyl[(Ci-C6)-Alkoxy]aminocarbonyl, (C2-C6)-Alkenylaminocarbonyl, (Ca-Ce)- Cycloalkylaminocarbonyl, Aryl-(CrC6)-alkylaminocarbonyl, Amino, (d-Ce)- Alkylamino, (Ca-CeJ-Cycloalkylamino, Bis[(Ci-C6)-Alkyl]amino steht, substituted phenyl, heteroaryl, heterocyclyl, (C3-Cc>) cycloalkyl, (C -CÖ) - alkenyl, (Ci-Ce) alkoxy, (Ci-C 6) -haloalkoxy, (Ci-C 6) -haloalkyl, (C 1 -C 6 ) -alkylthio, (C 1 -C 6 ) -haloalkylthio, hydroxycarbonyl, aryl- (C 1 -C 6 ) -alkoxycarbonyl, (C 2 -C 6 ) -alkenyloxycarbonyl, aminocarbonyl, (C 1 -C 6 -alkylaminocarbonyl, bis [(Ci -Ce) - alkyljaminocarbonyl, (C 1 -C 6) -alkyl [(C 1 -C 6) -alkyl] aminocarbonyl, (C 1 -C 6) -alkyl [(C 1 -C 6) -alkoxy] aminocarbonyl, (C 2 -C 6) -alkenylaminocarbonyl, (Ca -Ce) - cycloalkylaminocarbonyl, aryl- (C 1 -C 6) -alkylaminocarbonyl, amino, (C 1 -C 6) -alkylamino, (C 1 -C 6 -cycloalkylamino, bis [(C 1 -C 6) -alkyl] -amino,
R24, R25, R26, R28, R29 und R30 unabhängig voneinander für Wasserstoff, (CrC5)-Alkyl, Fluor, Chlor, Brom, lod, (Ca-CeJ-Cycloalkyl, Aryl, Heteroaryl, Heterocyclyl, (C2-C5)-Alkenyl, (Ci-C5)-Alkoxy, (Ci-C5)-Haloalkyl, (Ci-C5)-Alkylthio, (C1-C5)- Haloalkylthio stehen, R 24 , R 25 , R 26 , R 28 , R 29 and R 30 independently of one another represent hydrogen, (C 1 -C 5 ) -alkyl, fluorine, chlorine, bromine, iodine, (C 1 -C 6 -cycloalkyl, aryl, heteroaryl, heterocyclyl, (C 2 -C 5) alkenyl, (Ci-C 5) alkoxy, (Ci-C5) haloalkyl, (Ci-C 5) alkylthio, (C1-C5) - haloalkylthio stand,
A9 für O (Sauerstoff), S (Schwefel), N-H, N-CH3, N-OCH3 oder die Gruppierung CHR27 steht und wobei R27 in der Gruppierung CHR27 die Bedeutung gemäß der nachstehenden Definition hat und
R27 für Wasserstoff, Fluor, Chlor, Brom, lod, (Ci-C-5)-Alkyl, gegebenenfalls substituiertes Phenyl, Heteroaryl, Heterocyclyl, (Ca-Ce Cycloalkyl, (Cz-Ce)- Alkenyl, (Ci-C6)-Alkoxy, (Ci-C5)-Alkoxy-(Ci-C5)-alkyl, (Ci-C5)-Haloalkoxy, (CrC5)-Haloalkyl, (CrC5)-Alkylthio, (Ci-Cr.)-Haloalkylthio, Hydroxycarbonyl, (Ci-Cr>)-Alkoxycarbonyl, (Ca-Ce Cycloalkoxycarbonyl, Aryl-(CrCr>)- alkoxycarbonyl, Aminocarbonyl, (d-Cs^Alkylaminocarbonyl, Bis[(Ci-C5)- alkyl]aminocarbonyl, (Ca-CeJ-Cycloalkylaminocarbonyl, Aryl-(d-C6)- alkylaminocarbonyl, Amino, (d-CeJ-Alkylamino, (C3-C6)-Cycloalkylamino, Bis[(Ci-C5)-Alkyl]amino steht. A 9 is O (oxygen), S (sulfur), NH, N-CH 3 , N -OCH 3 or the moiety CHR 27 and wherein R 27 in the moiety CHR 27 has the meaning as defined below and R 27 represents hydrogen, fluorine, chlorine, bromine, iodine, (C 1 -C 5) -alkyl, optionally substituted phenyl, heteroaryl, heterocyclyl, (C 1 -C 6 -cycloalkyl, (C 2 -C 6) -alkenyl, (C 1 -C 6) ) alkoxy, (Ci-C 5) alkoxy (Ci-C 5) alkyl, (Ci-C 5) -haloalkoxy, (CrC 5) haloalkyl, (CrC 5) alkylthio, (Ci-Cr. ) haloalkylthio, hydroxycarbonyl, (C Cr>) alkoxycarbonyl, (Ca-Ce cycloalkoxycarbonyl, aryl (CrCr>) - alkoxycarbonyl, aminocarbonyl, (d-Cs ^ alkylaminocarbonyl, bis [(Ci-C5) - alkyl] aminocarbonyl , (C 1 -C 12 -cycloalkylaminocarbonyl, aryl- (C 1 -C 6) -alkylaminocarbonyl, amino, (C 1 -C 6 -alkylamino, (C 3 -C 6) -cycloalkylamino, bis [(C 1 -C 5 ) -alkyl] -amino.
Im besonders Speziellen bevorzugt ist die erfindungsgemäße Verwendung von Verbindungen der allgemeinen Formel (I), die durch die Formeln (la) bis (lo) beschrieben werden, Particularly particularly preferred is the use according to the invention of compounds of the general formula (I) which are described by the formulas (Ia) to (Io)
[X-Y] für die Gruppierung [X-Y] for grouping
[Χ-ΥΓ steht, [Χ-ΥΓ stands,
steht, wobei R7, R8, R9, R10, R11, R12, R13, R14, R17, R18, R19, R20, R22, R23, R24, R25, R26, R28, R29 und R30 und A1 bis A9 jeweils die Bedeutung gemäß der
nachstehenden Definitionen haben und wobei der Pfeil für eine Bindung zur jeweiligen Gruppierung C-R6 in den vorgenannten Formeln (la) bis (Ic) steht, where R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 17 , R 18 , R 19 , R 20 , R 22 , R 23 , R 24 , R 25 , R 26 , R 28 , R 29 and R 30 and A 1 to A 9 each have the meaning according to the have the following definitions and wherein the arrow for a bond to the respective group CR 6 is in the abovementioned formulas (Ia) to (Ic),
R5 für Hydroxy, Methoxy, Ethoxy, n-Propyloxy, Methylcarbonyloxy, R 5 is hydroxy, methoxy, ethoxy, n-propyloxy, methylcarbonyloxy,
Ethylcarbonyloxy, n-Propylcarbonyloxy, i-Propylcarbonyloxy, n- Butylcarbonyloxy, sec-Butylcarbonyloxy, tert.-Butylcarbonyloxy, n- Pentylcarbonyloxy, Phenylcarbonyloxy, p-CI-Phenylcarbonyloxy, p- Methylphenylcarbonyloxy, p-Trifluormethylphenylcarbonyloxy, p- Methoxyphenylcarbonyloxy, o-CI-Phenylcarbonyloxy, o- Methylphenylcarbonyloxy, o-Trifluormethylphenylcarbonyloxy, o- Methoxyphenylcarbonyloxy, 2-Pyridylcarbonyloxy, 3-Pyridylcarbonyloxy, 4- Pyridylcarbonyloxy, 6-Trifluormethyl-3-Pyridylcarbonyloxy, 4-Chlor-3- Pyridylcarbonyloxy, Cyclopropylcarbonyloxy, Cyclobutylcarbonyloxy, Ethylcarbonyloxy, n-propylcarbonyloxy, i -propylcarbonyloxy, n-butylcarbonyloxy, sec-butylcarbonyloxy, tert -butylcarbonyloxy, n-pentylcarbonyloxy, phenylcarbonyloxy, p-CI-phenylcarbonyloxy, p-methylphenylcarbonyloxy, p-trifluoromethylphenylcarbonyloxy, p-methoxyphenylcarbonyloxy, o-CI Phenylcarbonyloxy, o-methylphenylcarbonyloxy, o-trifluoromethylphenylcarbonyloxy, o-methoxyphenylcarbonyloxy, 2-pyridylcarbonyloxy, 3-pyridylcarbonyloxy, 4-pyridylcarbonyloxy, 6-trifluoromethyl-3-pyridylcarbonyloxy, 4-chloro-3-pyridylcarbonyloxy, cyclopropylcarbonyloxy, cyclobutylcarbonyloxy,
Cyclopentylcarbonyloxy, Cyclohexylcarbonyloxy, ethoxycarbonyloxy, Cyclopentylcarbonyloxy, cyclohexylcarbonyloxy, ethoxycarbonyloxy,
Ethoxycarbonyloxy, Trimethylsilyloxy, Triethylsilyloxy, Triisopropylsilyloxy Dirne thylphenylsilyloxy, tert.-Butyldimethylsilyloxy steht, Ethoxycarbonyloxy, trimethylsilyloxy, triethylsilyloxy, triisopropylsilyloxy, thylphenylsilyloxy, tert-butyldimethylsilyloxy,
R6 für Fluor, Chlor, Brom, lod, Cyano, Cyanomethyl, Trifluormethyl, R 6 represents fluorine, chlorine, bromine, iodine, cyano, cyanomethyl, trifluoromethyl,
Pentafluorethyl, Difluormethyl, Nitro, Amino, Hydroxy, Hydroxymethyl, Pentafluoroethyl, difluoromethyl, nitro, amino, hydroxy, hydroxymethyl,
Hydrothio, Thiocyanato, Isothiocyanato, Trifluormethylthio, Methylthio, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, iso-Butyl, tert.-Butyl, Hydroxy, Methoxy, Ethoxy, iso-Propyloxy, n-Propyloxy, n-Butyloxy, sec-Butyloxy, tert.-Butyloxy, n- Pentyloxy, Benzyloxy, p-Chlorbenzyloxy, p-Methoxybenzyloxy, p- Fluorbenzyloxy, p-Methylbenzyloxy, Difluormethoxy, Trifluormethoxy, 2,2- Difluorethoxy, 2,2,2-Trifluorethoxy, Phenoxy, p-Chlorphenoxy, p- Methylphenoxy, p-Fluorphenoxy, p-Methoxyphenoxy, p-Trifluormethylphenoxy, p-Trifluormethoxyphenoxy, m-Chlorphenoxy, m-Methylphenoxy, m- Fluorphenoxy, m-Methoxyphenoxy, m-Trifluormethylphenoxy, m- Trifluormethoxyphenoxy, o-Chlorphenoxy, o-Methylphenoxy, o-Fluorphenoxy, o- Methoxyphenoxy, o-Trifluormethylphenoxy, o-Trifluormethoxyphenoxy, 2,4- Dichlorphenoxy, 3,5-Dichlorphenoxy, 3,4-Dichlorphenoxy, 2,5-Dichlorphenoxy, Cyclopropyimethyioxy, Hydroxycarbonyl, Methoxycarbonyi, Ethoxycarbonyi, n- Propyloxycarbonyl, iso-Propyloxycarbonyl, n-Butyloxycarbonyl, sec- Butyloxycarbonyl, iso-Butyloxycarbonyl, tert.-Butyloxycarbonyl, n-
Pentyloxycarbonyl, neo-Pentyloxycarbonyl, n-Hexyloxycarbonyl, Hydrothio, thiocyanato, isothiocyanato, trifluoromethylthio, methylthio, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, tert-butyl, hydroxy, methoxy, ethoxy, iso-propyloxy, n-propyloxy, n Butyloxy, sec-butyloxy, tert -butyloxy, n-pentyloxy, benzyloxy, p-chlorobenzyloxy, p-methoxybenzyloxy, p-fluorobenzyloxy, p-methylbenzyloxy, difluoromethoxy, trifluoromethoxy, 2,2-difluoroethoxy, 2,2,2- Trifluoroethoxy, phenoxy, p-chlorophenoxy, p-methylphenoxy, p-fluorophenoxy, p-methoxyphenoxy, p-trifluoromethylphenoxy, p-trifluoromethoxyphenoxy, m-chlorophenoxy, m-methylphenoxy, m-fluorophenoxy, m-methoxyphenoxy, m-trifluoromethylphenoxy, m- Trifluoromethoxyphenoxy, o-chlorophenoxy, o-methylphenoxy, o-fluorophenoxy, o-methoxyphenoxy, o-trifluoromethylphenoxy, o-trifluoromethoxyphenoxy, 2,4-dichlorophenoxy, 3,5-dichlorophenoxy, 3,4-dichlorophenoxy, 2,5-dichlorophenoxy, Cyclopropylmethoxy, hydroxycarbonyl, methoxycarbonyi, ethoxycarbonyi, n-propyloxycarbonyl, iso-propyloxycarbonyl, n-butyloxycarbonyl, s ec-butyloxycarbonyl, iso-butyloxycarbonyl, tert-butyloxycarbonyl, n- Pentyloxycarbonyl, neo-pentyloxycarbonyl, n-hexyloxycarbonyl,
Benzyloxycarbonyl, p-Chlorbenzyloxycarbonyl, p-Methoxybenzyloxycarbonyl, p- Fluorbenzyloxycarbonyl, p-Methylbenzyloxycarbonyl, Allyloxycarbonyl, Benzyloxycarbonyl, p-chlorobenzyloxycarbonyl, p-methoxybenzyloxycarbonyl, p-fluorobenzyloxycarbonyl, p-methylbenzyloxycarbonyl, allyloxycarbonyl,
Methoxyethoxycarbonyl, Ethoxyethoxycarbonyl , Ethoxymethoxycarbonyl, Methoxy-n-propyloxycarbonyl, Ethoxy-n-propoxycarbonyl, Methoxyethoxycarbonyl, ethoxyethoxycarbonyl, ethoxymethoxycarbonyl, methoxy-n-propyloxycarbonyl, ethoxy-n-propoxycarbonyl,
Cyclopropyloxycarbonyl, Cyclobutyloxycarbonyl, Cyclopentyloxycarbonyl, Cyclohexyloxycarbonyl, (C2-Cö)-alkinyloxycarbonyl, 2,2,-Difluorethoxycarbonyl, 2,2.2-Trifluorethoxycarbonyl, Methylaminocarbonyl, Ethylaminocarbonyl, n- Propylaminocarbonyl, iso-Propylaminocarbonyl, n-Butylaminocarbonyl, iso- Butylaminocarbonyl, tert.-Butylaminocarbonyl, n-Pentylaminocarbonyl, neo- Pentylaminocarbonyl, iso-Pentylaminocarbonyl, Cyclopropylaminocarbonyl, Cyclobutylaminocarbonyl, Cyclopentylaminocarbonyl, Cyclopropyloxycarbonyl, cyclobutyloxycarbonyl, cyclopentyloxycarbonyl, cyclohexyloxycarbonyl, (C 2 -C 6) -alkynyloxycarbonyl, 2,2'-difluoroethoxycarbonyl, 2,2,2-trifluoroethoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n -propylaminocarbonyl, iso -propylaminocarbonyl, n-butylaminocarbonyl, isobutylaminocarbonyl, tert -Butylaminocarbonyl, n-pentylaminocarbonyl, neopentylaminocarbonyl, isopentylaminocarbonyl, cyclopropylaminocarbonyl, cyclobutylaminocarbonyl, cyclopentylaminocarbonyl,
Cyclohexylaminocarbonyl, Piperidinyl-N-carbonyl, Pyrrolidinyl-N-carbonyl, Cyanomethylaminocarbonyl, Cyanoethylaminocarbonyl, Cyclohexylaminocarbonyl, piperidinyl-N-carbonyl, pyrrolidinyl-N-carbonyl, cyanomethylaminocarbonyl, cyanoethylaminocarbonyl,
Dimethylaminocarbonyl, Diethylaminocarbonyl, Ethyl(methyl)aminocarbonyl, Diisopropylaminocarbonyl, Methoxyethylaminocarbonyl, Dimethylaminocarbonyl, diethylaminocarbonyl, ethyl (methyl) aminocarbonyl, diisopropylaminocarbonyl, methoxyethylaminocarbonyl,
Ethoxyethylaminocarbonyi, (C2-C6)-alkinylaminocarbonyl, Methylsulfonylamino, Ethylsulfonylamino, iso-Propylsulfonylamino, Cyclopropylsulfonylamino, Phenyisuifonylamino, p-Chlorphenylsulfonylamino, o-Chlorphenylsulfonylamino, m-Chlorphenylsulfonylamino, p-Fluorphenylsulfonylamino, o- Fluorphenylsulfonylamino, m-Fluorphenylsulfonylamino, p- lodphenylsulfonylamino, o-lodphenylsulfonylamino, m- lodphenylsulfonylamino,p-Methoxyphenylsulfonylamino, o- Methoxyphenylsulfonylamino, m-Methoxyphenylsulfonylamino, p- Trifluormethylphenylsulfonylamino, o-Trifluormethylphenylsulfonylamino, m- Trifluormethylphenylsulfonylamino, p-Methylphenylsulfonylamino, o- Methylphenylsulfonylamino, m-Methylphenylsulfonylamino, Ethoxyethylaminocarbonyi, (C2-C6) -alkinylaminocarbonyl, methylsulfonylamino, ethylsulfonylamino, iso-propylsulfonylamino, Cyclopropylsulfonylamino, Phenyisuifonylamino, p-chlorophenylsulfonylamino, o-chlorophenylsulfonylamino, m-chlorophenylsulfonylamino, p-fluorophenylsulfonylamino, o- fluorophenylsulfonylamino, m-fluorophenylsulfonylamino, p-lodphenylsulfonylamino, o-iodophenylsulfonylamino, m-iodophenylsulfonylamino, p-methoxyphenylsulfonylamino, o-methoxyphenylsulfonylamino, m-methoxyphenylsulfonylamino, p-trifluoromethylphenylsulfonylamino, o-trifluoromethylphenylsulfonylamino, m-trifluoromethylphenylsulfonylamino, p-methylphenylsulfonylamino, o-methylphenylsulfonylamino, m-methylphenylsulfonylamino,
Methoxycarbonylamino, Ethoxycarbonylamino, n-Propyloxycarbonylamino, iso- Propyloxycarbonylamino, tert.-Butyloxycarbonylamino, n- Butyloxycarbonylamino,Methylamino, Ethylamino, n-Propylamino, iso- Propylamino, Cyclopropylamino, Cyclobutylamino, Cyclopentylamino, Methoxycarbonylamino, ethoxycarbonylamino, n-propyloxycarbonylamino, isopropyloxycarbonylamino, tert-butyloxycarbonylamino, n-butyloxycarbonylamino, methylamino, ethylamino, n-propylamino, iso-propylamino, cyclopropylamino, cyclobutylamino, cyclopentylamino,
Methylcarbonylamino, Ethylcarbonylamino, n-Propylcarbonylamino, iso- Propylcarbonylamino, n-Butylcarbonylamino, iso-Butylcarbonylamino, tert.- Butylcarbonylamino, Cyclopropycarbonylamino, Phenylcarbonylamino, Formyl,
Methylcarbonyloxy, Ethylcarbonyloxy, n-Propylcarbonyloxy, iso- Propylcarbonyloxy, n-Butylcarbonyloxy, tert.-Butylcarbonyloxy, Methylcarbonylamino, ethylcarbonylamino, n-propylcarbonylamino, iso-propylcarbonylamino, n-butylcarbonylamino, iso-butylcarbonylamino, tert-butylcarbonylamino, cyclopropycarbonylamino, phenylcarbonylamino, formyl, Methylcarbonyloxy, ethylcarbonyloxy, n-propylcarbonyloxy, iso -propylcarbonyloxy, n-butylcarbonyloxy, tert-butylcarbonyloxy,
Cyclopropylcarbonyloxy, Cyclobutylcarbonyloxy, Cyclopentylcarbonyloxy, Cyclohexylcarbonyloxy, Aminosulfonyl, Methylaminosulfonyl, Cyclopropylcarbonyloxy, cyclobutylcarbonyloxy, cyclopentylcarbonyloxy, cyclohexylcarbonyloxy, aminosulfonyl, methylaminosulfonyl,
Ethylaminosulfonyl, n-Propylaminosulfonyl, iso-Propylaminosulfonyl, n- Butylaminosulfonyl, tert.-Butylaminosulfonyl, iso-Butylaminosulfonyl, Ethylaminosulfonyl, n-propylaminosulfonyl, iso-propylaminosulfonyl, n-butylaminosulfonyl, tert-butylaminosulfonyl, iso-butylaminosulfonyl,
Cyclopropylaminosulfonyl, Hydroxyiminomethyl, ethoxyiminomethyl, Cyclopropylaminosulfonyl, hydroxyiminomethyl, ethoxyiminomethyl,
Ethoxyiminomethyl, n-Propyloxyiminomethyl, iso-Propyloxyiminomethyl, n- Butyloxyiminomethyl, iso-Butyloxyiminomethyl, tert.-Butyloxyiminomethyl, Cyclopropylmethoxyiminomethyl, (Ci-C6)-Alkoxycarbonyl-heterocyclyl-N- carbonyl, (Ci-C6)-Alkoxycarbonyl-(CrC6)-alkyl-heterocyclylidenaminocarbonyl, (Ci-C6)-Alkoxycarbonylheterocyclyliden-(Ci-C6)-alkylaminocarbonyl, (d-Ce)- Alkoxycarbonyl-(Ci-C6)-Alkylaminocarbonyl, (Ci-C6)-Alkoxycarbonyl-(Ci-C6)- Alkyl((CrC6)-alkyl)aminocarbonyl, (Ci-C6)-Alkoxycarbonyl-(C;rCö)- cycloalkylidenaminocarbonyl, (Ci-CeJ-AlkoxycarbonyKCa-Ce)- cycloalkylaminocarbonyl, Aminocarbonyl, (C3-C5)-Cycloalkyl-(CrC5)- alkoxycarbonyl, , (C2-C5)-Alkenyloxy-(Ci-C5)-alkoxycarbonyl, (C1-C5)- Alkylamino-(Ci-C5)-alkoxycarbonyl, Tris[(Ci-Cr>)-alkyl]silyloxy-(Ci-C5)- alkoxycarbonyl, Bis[(Ci-C5)-Alkyl]amino-(Ci-C5)-alkoxycarbonyl, (C1-C5)- Alkyl[(Ci-C5)-alkyl]amino-(Ci-C5)-alkoxycarbonyl, Cyano-(Ci-Cr>)- alkoxycarbonyl, Heterocyclyl-N-(CrC5)-alkoxycarbonyl, Heteroaryioxycarbonyl, Heteroaryl-(Ci-C5)-alkoxycarbonyl, Heterocyclyl-(Ci-C5)-alkoxycarbonyl, Heterocyclyloxycarbonyl, (C2-C5)-Alkenyl-(Ci-C5)-alkoxycarbonyl, (C2-C5)- Alkinyl-(CrC5)-alkoxycarbonyl, Aryl-(C2-C5)-alkinyloxycarbonyl, Aryl-(C2-Cs)- alkenyloxycarbonyl, (Ci-C5)-Alkyl[(Ci-C5)-Alkoxy]aminocarbonyl, (C2-C5)- Alkenylaminocarbonyl, Arylaminocarbonyl, Aryl-(Ci-C5)-alkylaminocarbonyl, Heteroaryl-(Ci-C5)-alkylaminocarbonyl, (Ci-C5)-Haloalkylaminocarbonyl, (C2-C5)-Alkinyl-(Ci-C5)-alkylaminocarbonyl, (C1-C5)- AlkoxycarbonylaminocarbonyL Aryl-(Ci-C5)-alkoxycarbonylaminocarbonyl, Hydroxycarbonyl-(Ci-C5)-alkyl, (Ci-C5)-Alkoxycarbonyl-(Ci-C5)-alkyl, (C3-C6)- Cycloalkoxycarbonyl-(Ci-C5)-alkyl, (C3-C6)-Cycloalkyl-(Ci-C5)-alkoxycarbonyl- (CrC5)-alkyl, (C2-C5)-Alkenyloxycarbonyl-(Ci-Cr>)-alkyl, Aryl-(CrC5)- alkoxycarbonyl-(Ci-Cr>)-alkyl, (Ci-C5)-Alkylaminocarbonyl-(Ci-C5)-alkyl, Aminocarbonyl-(Ci-C5)-alkyl, Bis[(Ci-C5)-alkyl]aminocarbonyl-(Ci-C5)-alkyl,
(C3-C6)-Cycloalkylaminocarbonyl-(Ci-C5)-alkyl, Aryl-(Ci-C5)-alkylaminocarbonyl- (Ci-Cs)-alkyl, Heteroaryl-(CrC5)-alkylaminocarbonyl-(Ci-C5)-alkyl, Cyano- (Ci-C5)-alkylaminocarbonyl-(Ci-C5)-alkyl, (Ci-Cr>)-Haloalkylaminocarbonyl- (Ci-C5)-alkyl, (C2-C5)-Alkinyl-(Ci-C5)-alkylaminocarbonyl-(Ci-C5)-alkyl, (C3-C6)- Cycloaikyi-(Ci-C5)-alkylaminocarbonyl-(Ci-C5)-alkyl, (C1-C5)- Alkoxycarbonylaminocarbonyl-(Ci-C5)-alkyl, Aryl-(Ci-Cs)- alkoxycarbonylaminocarbonyl-(Ci-Cr))-alkyl, Hydroxycarbonyl-(Ci-C5)- alkylaminocarbonyl, Aryl-(Ci-C5)-alkoxycarbonyl-(Ci-C5)-alkylaminocarbonyl, Aminocarbonyl-(Ci-C5)-alkylaminocarbonyl, (Ci-C5)-Alkylaminocarbonyl- (Ci-C5)-alkylaminocarbonyl. Ethoxyiminomethyl, n-propyloxyiminomethyl, iso-propyloxyiminomethyl, n-butyloxyiminomethyl, iso-butyloxyiminomethyl, tert-butyloxyiminomethyl, cyclopropylmethoxyiminomethyl, (C 1 -C 6) -alkoxycarbonyl-heterocyclyl-N-carbonyl, (C 1 -C 6) -alkoxycarbonyl- (C 1 -C 6) -alkyl-heterocyclylideneaminocarbonyl, (C 1 -C 6) -alkoxycarbonylheterocyclylideno (C 1 -C 6) -alkylaminocarbonyl, (C 1 -C 6) -alkoxycarbonyl- (C 1 -C 6) -alkylaminocarbonyl, (C 1 -C 6) -alkoxycarbonyl- (C 1 -C 6) Alkyl ((C 1 -C 6) -alkyl) aminocarbonyl, (C 1 -C 6) -alkoxycarbonyl- (C 1 -C 6) -cycloalkylideneaminocarbonyl, (C 1 -C 6 -alkoxycarbonyKCa-Ce) -cycloalkylaminocarbonyl, aminocarbonyl, (C 3 -C 5) -cycloalkyl- CrC 5) - alkoxycarbonyl,, (C 2 -C 5) alkenyloxy- (C 1 -C 5) -alkoxycarbonyl, (C 1 -C 5) -alkylamino- (C 1 -C 5) -alkoxycarbonyl, tris [(Ci-Cr) -alkyl] silyloxy - (C 1 -C 5) -alkoxycarbonyl, bis [(C 1 -C 5) -alkyl] amino- (C 1 -C 5) -alkoxycarbonyl, (C 1 -C 5) -alkyl [(C 1 -C 5) -alkyl] amino- (C 1 -C 4) -alkyl C5) alkoxycarbonyl, cyano (Ci-Cr) alkoxycarbonyl, heterocyclyl-N- (CrC5) alkoxycarbonyl, heteroaryioxycarbonyl, hetero aryl- (C 1 -C 5) -alkoxycarbonyl, heterocyclyl- (C 1 -C 5) -alkoxycarbonyl, heterocyclyloxycarbonyl, (C 2 -C 5) -alkenyl- (C 1 -C 5) -alkoxycarbonyl, (C 2 -C 5) -alkynyl- (C 1 -C 5) - alkoxycarbonyl, aryl- (C 2 -C 5) -alkynyloxycarbonyl, aryl- (C 2 -C 5) -alkenyloxycarbonyl, (C 1 -C 5) -alkyl [(C 1 -C 5) -alkoxy] -aminocarbonyl, (C 2 -C 5) -alkenylaminocarbonyl, arylaminocarbonyl, Aryl- (C 1 -C 5 ) -alkylaminocarbonyl, heteroaryl- (C 1 -C 5 ) -alkylaminocarbonyl, (C 1 -C 5 ) -haloalkylaminocarbonyl, (C 2 -C 5 ) -alkynyl- (C 1 -C 5 ) -alkylaminocarbonyl, (C 1 -C 5 ) - AlkoxycarbonylaminocarbonyL aryl- (Ci-C5) -alkoxycarbonylaminocarbonyl, hydroxycarbonyl- (Ci-C 5) alkyl, (Ci-C 5) alkoxycarbonyl (Ci-C 5) alkyl, (C 3 -C 6) - cycloalkoxycarbonyl (Ci-C5) alkyl, (C3-C6) cycloalkyl (Ci-C5) alkoxycarbonyl (-C 5) alkyl, (C2-C5) -Alkenyloxycarbonyl- (Ci-Cr>) alkyl , aryl (-C 5) - alkoxycarbonyl (C Cr>) alkyl, (Ci-C5) alkylaminocarbonyl (Ci-C5) alkyl, aminocarbonyl (C-C5) alkyl, bis [(Ci C5) alkyl] aminocarbonyl (Ci-C5) alkyl, (C 3 -C 6) -cycloalkylaminocarbonyl- (C 1 -C 5) -alkyl, aryl- (C 1 -C 5) -alkylaminocarbonyl- (C 1 -C 8) -alkyl, heteroaryl- (C 1 -C 5) -alkylaminocarbonyl- (C 1 -C 5) -alkyl, cyano- (Ci-C5) alkylaminocarbonyl (Ci-C5) alkyl, (Ci-Cr>) -Haloalkylaminocarbonyl- (Ci-C 5) alkyl, (C2-C5) alkynyl (C 5) alkylaminocarbonyl (Ci-C 5) alkyl, (C 3 -C 6) - Cycloaikyi- (Ci-C 5) alkylaminocarbonyl (Ci-C 5) alkyl, (C1-C5) - Alkoxycarbonylaminocarbonyl- (C -C5) -alkyl, aryl- (C 1 -C 8) -alkoxycarbonylaminocarbonyl- (C 1 -C 8)) -alkyl, hydroxycarbonyl- (C 1 -C 5) -alkylaminocarbonyl, aryl- (C 1 -C 5) -alkoxycarbonyl- (C 1 -C 5) alkylaminocarbonyl, aminocarbonyl- (C 1 -C 5) -alkylaminocarbonyl, (C 1 -C 5) -alkylaminocarbonyl- (C 1 -C 5) -alkylaminocarbonyl.
(C3-C6)-Cycloalkylaminocarbonyl-(Ci-C5)-alkylaminocarbonyl, (C3-C5)- Cycloalkyl-(CrC5)-alkylaminocarbonyl, (C3-C6)-Cycloalkyl-(Ci-C5)- alkylaminocarbonyl-(Ci-C5)-alkyl, (C3-C5)-Cycloalkyl-(Ci-C6)- alkylaminocarbonyl-(Ci-C5)-alkylaminocarbonyl, (C2-C5)-Alkenyl-(d-C5)- alkylaminocarbonyl, (C2-C5)-Alkenylaminocarbonyl-(Ci-C5)-alkyl, (C2-C5)- Alkenyl-(Ci-C5)-alkylaminocarbonyl-(Ci-C5)-alkyi, (CrC5)-Alkylcarbonyl, (C3-C5)- Cycloalkylcarbonyl, Arylcarbonyl, Formyl, Hydroxyiminomethyl, (C 3 -C 6 ) -cycloalkylaminocarbonyl- (C 1 -C 5 ) -alkylaminocarbonyl, (C 3 -C 5 ) -cycloalkyl- (C 1 -C 5 ) -alkylaminocarbonyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 5 ) -alkylaminocarbonyl- (C 1 -C 5 ) -alkyl, (C 3 -C 5 ) -cycloalkyl- (C 1 -C 6 ) -alkylaminocarbonyl- (C 1 -C 5 ) -alkylaminocarbonyl, (C 2 -C 5 ) -alkenyl- (C 1 -C 5 ) - alkylaminocarbonyl, (C 2 -C 5 ) -alkenylaminocarbonyl- (C 1 -C 5 ) -alkyl, (C 2 -C 5 ) -alkenyl- (C 1 -C 5 ) -alkylaminocarbonyl- (C 1 -C 5 ) -alkyl, (C 1 -C 5 ) -alkylcarbonyl, (C3-C5) - cycloalkylcarbonyl, arylcarbonyl, formyl, hydroxyiminomethyl,
AminoiminomethyL (Ci-C5)-Alkoxyiminomethyl, (Ci-C5)-Alkylaminoiminomethyl, Bis[(Ci-C5)-alkyl]aminoiminomethyl, (C3-Cr>)-Cycloalkoxyiminomethyl, (CS-CG)- Cycloalkyl-(Ci-C5)-alkoximinomethyl, Aryloximinomethyl, Aryl-(Ci-Cs)- alkoxyiminomethyl, Aryl-(Ci-C5)-alkylaminoiminomethyl, (C2-C5)- Alkenyloxyiminomethyl, Aryiaminoiminomethyl, Arylsulfonylaminoiminomethyl, Heteroaryl-(CrC5)-aikyl, Heterocyclyl-(Ci-C5)-alkyi, Aminoiminomethyl (Ci-C5) alkoxyiminomethyl, (Ci-C5) -Alkylaminoiminomethyl, bis [(Ci-C5) alkyl] aminoiminomethyl (C3-Cr>) -Cycloalkoxyiminomethyl, (CS-CG) - cycloalkyl- (Ci-C5 ) -alkoximinomethyl, aryloximinomethyl, aryl- (C 1 -C 5 ) -alkoxyiminomethyl, aryl- (C 1 -C 5 ) -alkylaminoiminomethyl, (C 2 -C 5 ) -alkenyloxyiminomethyl, aryiaminoiminomethyl, arylsulfonylaminoiminomethyl, heteroaryl- (C 1 -C 5 ) -acyl, heterocyclyl ( Ci-C 5 ) -alkyi,
Hydroxycarbonylheterocyclyl, (Ci-C5)-Alkoxycarbonylheterocyclyl, (C2-C5)- Alkenyloxycarbonylheterocyclyl, (C-2-C5)-Alkenyl-(Ci-C5)- alkoxycarbonylheterocyclyi, Aryl-(Ci-C5)-aikoxycarbonylheterocyclyi, (Ca-Ce)- Cycloalkoxycarbonylheterocyclyl, (C3-C5)-Cycloalkyl-(Ci-C5)- alkoxycarbonyiheterocyclyl, Aminocarbonyiheterocyclyl, (C1-C5)- AlkylaminocarbonylheterocyclyL Bis[(Ci-C5)-Alkyl]aminocarbonylheterocyclyl, (C3-C6)-Cycloalkylaminocarbonylheterocyclyl, Aryl-(Ci-C5)- alkylaminocarbonylheterocyclyl, (C2-C5)-Aikenylaminocarbonylheterocyclyl, Hydroxycarbonylheterocyclyl-(CrC5)-alkyl, (Ci-Cr>)-Alkoxycarbonylheterocyclyl- (Ci-C5)-alkyl, Hydroxycarbonyl-(C3-C6)-cycloalkyl-(Ci-C5)-alkyl, (C1-C5)- Alkoxycarbonyl-(C3-C5)-cycloalkyl-(Ci-C6)-aikyl, Hydroxyaminocarbonyl,
(Ci-C5)-Alkoxyaminocarbonyl, Aryl-(Ci-C5)-alkoxyaminocarbonyl, Heterocyclyl steht, Hydroxycarbonylheterocyclyl, (C 1 -C 5) -alkoxycarbonylheterocyclyl, (C 2 -C 5) -alkenyloxycarbonylheterocyclyl, (C 2 -C 5) -alkenyl- (C 1 -C 5) -alkoxycarbonylheterocyclyl, aryl- (C 1 -C 5) -aikoxycarbonylheterocyclyl, (Ca-Ce ) - Cycloalkoxycarbonylheterocyclyl, (C3-C5) -cycloalkyl- (Ci-C5) -alkoxycarbonyiheterocyclyl, Aminocarbonyiheterocyclyl, (C1-C5) -alkylaminocarbonylheterocyclyl Bis [(Ci-C5) -alkyl] aminocarbonylheterocyclyl, (C3-C6) -cycloalkylaminocarbonylheterocyclyl, aryl - (Ci-C5) - alkylaminocarbonylheterocyclyl, (C2-C5) -Aikenylaminocarbonylheterocyclyl, hydroxycarbonylheterocyclyl (CrC5) alkyl, (Ci-Cr > ) alkoxycarbonylheterocyclyl (Ci-C 5 ) alkyl, hydroxycarbonyl (C3-C 6 ) -cycloalkyl- (C 1 -C 5 ) -alkyl, (C 1 -C 5 ) -alkoxycarbonyl- (C 3 -C 5 ) -cycloalkyl- (C 1 -C 6) -acyl, hydroxyaminocarbonyl, (C 1 -C 5) -alkoxyaminocarbonyl, aryl- (C 1 -C 5) -alkoxyaminocarbonyl, heterocyclyl,
R7, R8 , R9 und R10 unabhängig voneinander für Wasserstoff, Fluor, Chlor, Brom, lod, Nitro, Amino, Cyano, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, sec-Butyl, tert.- Butyl, Phenyl, Cyclopropyl, Cyclobutyl, Hydroxy, Methoxy, Ethoxy, R 7 , R 8 , R 9 and R 10 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, nitro, amino, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, phenyl, cyclopropyl, cyclobutyl, hydroxy, methoxy, ethoxy,
Trifluormethyl, Difluormethyl, Trifluormethoxy, Difluormethoxy, Hydrothio, Methylthio, Trifluormethylthio, Methoxycarbonyl, Ethoxycarbonyl, iso- Propyloxycarbonyl, n-Propyloxycarbonyl, iso-Propyloxycarbonyl, tert.- Butyloxycarbonyl stehen, Trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, hydrothio, methylthio, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, iso-propyloxycarbonyl, n-propyloxycarbonyl, iso-propyloxycarbonyl, tert-butyloxycarbonyl,
A\ A2, A3 und A4 gleich oder verschieden sind und unabhängig voneinander für N A \ A 2 , A 3 and A 4 are the same or different and are independently N
(Stickstoff) oder die Gruppierungen C-H, C-CH3, C-F, C-Cl, C-Br, C-l, C-OCF3, C-OCH3, C-CF3, C-CO2H, C-CO2CH3 stehen, wobei jedoch in keinem Fall mehr als zwei N-Atome benachbart sind, (Nitrogen) or the groupings CH, C-CH 3, CF, C-Cl, C-Br, CI, C-OCF3, C-OCH3, C-CF 3, C-CO2H, C-CO2CH3 are, but using in no case are more than two N atoms adjacent,
R11 und R12 unabhängig voneinander für Wasserstoff, Fluor, Chlor, Brom, lod, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, sec-Butyl, tert.-Butyl, Phenyl, Cyclopropyl, Cyclobutyl, Trifluormethyl, Difluormethyl, Methoxycarbonyl, Ethoxycarbonyl, iso- Propyloxycarbonyl, n-Propyloxycarbonyl, tert.-Butyloxycarbonyl stehen, R 11 and R 12 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, phenyl, cyclopropyl, cyclobutyl, trifluoromethyl , Di-propyloxycarbonyl, n-propyloxycarbonyl
A5 für S (Schwefel), O (Sauerstoff) oder die Gruppierungen N-H, N-CH3, N-CH2CH3, N- CH(CH3)2, N-C02t-Bu, N-Aryl, N-Heteroaryl, N-Heterocyclyl steht, A 5 for S (sulfur), O (oxygen) or the groupings NH, N-CH 3 , N-CH 2 CH 3 , N-CH (CH 3 ) 2 , N-CO 2 t-Bu, N-aryl, N-heteroaryl , N-heterocyclyl,
R13, R14, R17 und R18 unabhängig voneinander für Wasserstoff, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, Fluor, Chlor, Brom, lod, Trifluormethyl stehen oder R 13 , R 14 , R 17 and R 18 are independently hydrogen, methyl, ethyl, n-propyl, iso-propyl, n-butyl, fluorine, chlorine, bromine, iodine, trifluoromethyl or
R13 und R17 mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls weiter substituierten 5 bis 7-gliedrigen Ring bilden, R 13 and R 17 with the atoms to which they are attached form a completely saturated or partially saturated, optionally further substituted 5 to 7-membered ring,
A6, A7 gleich oder verschieden sind und unabhängig voneinander für O (Sauerstoff), S (Schwefel), N-H, N-OCH3, N-CH3 oder die Gruppierung CR15R16 stehen, wobei jedoch in keinem Fall zwei N-, O- oder S-Atome benachbart sind, und wobei R15
und R16 in der Gruppierung CR15R16 jeweils gleiche oder verschiedene A 6 , A 7 are identical or different and independently of one another are O (oxygen), S (sulfur), NH, N-OCH 3, N-CH 3 or the group CR 15 R 16 , but in no case are two N , O or S atoms are adjacent, and wherein R 15 and R 16 in the group CR 15 R 16 are each the same or different
Bedeutungen gemäß der nachstehenden Definition haben und Have meanings as defined below and
R15 und R16 unabhängig voneinander für Wasserstoff, Fluor, Chlor, Brom, lod, Methyl, Ethyl, n-Propyl, iso-Propyl, Phenyl, Methoxy, Ethoxy, Trifluormethyl, R 15 and R 16 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, phenyl, methoxy, ethoxy, trifluoromethyl,
Trifluormethoxy, Methylthio stehen, Trifluoromethoxy, methylthio,
R19, R20, R22 und R23 unabhängig voneinander für Wasserstoff, Methyl, Ethyl, n-Propyl, iso-Propyl, Fluor, Chlor, Brom, lod, Phenyl, Trifluormethyl stehen, R 19 , R 20 , R 22 and R 23 are each independently hydrogen, methyl, ethyl, n-propyl, iso-propyl, fluorine, chlorine, bromine, iodine, phenyl, trifluoromethyl,
A8 für O (Sauerstoff), S (Schwefel), N-H, N-CH3, N-OCH3 oder die Gruppierung CHR21 steht und wobei R21 in der Gruppierung CHR21 die Bedeutung gemäß der nachstehenden Definition hat, R21 für Wasserstoff, Fluor, Chlor, Brom, lod, Methyl, Ethyl, Methoxy, Ethoxy, A 8 is O (oxygen), S (sulfur), NH, N-CH 3 , N-OCH 3 or the moiety CHR 21 , and wherein R 21 in the moiety CHR 21 is as defined below, R 21 is Hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, methoxy, ethoxy,
Trifluormethyl, Trifluormethoxy, Methylthio, Phenyl, Hydroxycarbonyl, Trifluoromethyl, trifluoromethoxy, methylthio, phenyl, hydroxycarbonyl,
Benzyloxycarbonyl steht, Benzyloxycarbonyl stands,
R24, R25, R26, R28, R29 und R30 unabhängig voneinander für Wasserstoff, Methyl, Ethyl, n-Propyl, iso-Propyl, Fluor, Chlor, Brom, lod, Phenyl, Trifluormethyl, Methylthio stehen, R 24 , R 25 , R 26 , R 28 , R 29 and R 30 independently of one another represent hydrogen, methyl, ethyl, n-propyl, isopropyl, fluorine, chlorine, bromine, iodine, phenyl, trifluoromethyl, methylthio,
A9 für O (Sauerstoff), S (Schwefel), N-H, N-CH3, N-OCH3 oder die Gruppierung CHR27 steht und wobei R27 in der Gruppierung CHR27 die Bedeutung gemäß der nachstehenden Definition hat und A 9 is O (oxygen), S (sulfur), NH, N-CH 3, N -OCH 3 or the moiety CHR 27 and wherein R 27 in the moiety CHR 27 has the meaning as defined below and
R27 für Wasserstoff, Fluor, Chlor, Brom, lod, Methyl, Ethyl, Methoxy, Ethoxy, R 27 represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, methoxy, ethoxy,
Trifluormethyl, Trifluormethoxy, Methylthio, Hydroxycarbonyl, Methoxycarbonyl, Ethoxycarbonyl steht. Trifluoromethyl, trifluoromethoxy, methylthio, hydroxycarbonyl, methoxycarbonyl, ethoxycarbonyl.
Die oben aufgeführten allgemeinen oder in Vorzugsbereichen aufgeführten The general or preferred ones listed above
Restedefinitionen gelten sowohl für die Endprodukte der allgemeinen Formel (I) als auch entsprechend für die jeweils zur Herstellung benötigten Ausgangs- oder
Zwischenprodukte. Diese Restedefinitionen können untereinander, also auch zwischen den angegebenen bevorzugten Bereichen beliebig kombiniert werden. Residue definitions apply both to the end products of the general formula (I) and correspondingly to the starting material or preparation required in each case for the preparation Intermediates. These remainder definitions can be combined with one another as desired, ie also between the specified preferred ranges.
Im Wesentlichen sind die zuvor genannten substituierten 1 -(Arylethinyl)-, 1 - (Heteroarylethinyl)-, 1 -(Heterocyclyiethinyl)- und 1 -(Cyloalkenylethinyl)-cyclohexanole der allgemeinen Formel (I) ebenfalls noch nicht im Stand der Technik bekannt. Somit gelten als weiterer Teil der Erfindung 1 -(Arylethinyl)-, 1 -(Heteroarylethinyl)-, 1 - (Heterocyclylethinyl)- und 1-(Cyloalkenylethinyl)-cyclohexanole der allgemeinen Formel (I), In essence, the abovementioned substituted 1 - (arylethynyl) -, 1 - (heteroarylethynyl) -, 1 - (Heterocyclyiethinyl) - and 1 - (cycloalkenylethynyl) cyclohexanols of the general formula (I) are also not yet known in the art. Thus, another part of the invention is 1 - (arylethynyl) -, 1 - (heteroarylethynyl) -, 1- (heterocyclylethynyl) - and 1- (cycloalkenylethynyl) cyclohexanols of the general formula (I),
worin wherein
[X-Y] für die Gruppierung [X-Y] for grouping
[Χ-ΥΓ steht. [Χ-ΥΓ stands.
Q für die Gruppierungen Q-1 bis Q-6 Q for the groupings Q-1 to Q-6
Q-1 Q-2 Q-3 Q-1 Q-2 Q-3
Q-4 Q-5 und Q-6
sieht, wobei R7, R8, R9, R10, R11 , R12, R13, R14, R17, R18, R19, R20, R22, R23, R24, R25, R26, R28, R29 und R30 und A1 bis A9 jeweils die Bedeutung gemäß der nachstehenden Definitionen haben und wobei der Pfeil für eine Bindung zur jeweiligen Gruppierung C-R6 in der allgemeinen Formel (I) steht, für (Ci-C7)-Alkyl, (C3-C7)-Cycloalkyl, (C4-C7)-Cycloalkenyl, (C2-C7)-Alkenyl, (C2-C7)-Alkinyl, (C2-C7)-Alkenyl-(Ci-C7)-alkyl, (C2-C7)-Alkinyl-(Ci-C7)-alkyl, (Ci-C7)-Alkoxy-(Ci-C7)-alkyl, Hydroxy-(Ci-C7)-alkyl, (Ci-C7)-Haloalkyl, (C2-C7)- Haloalkenyl, (C2-C7)-Haloalkinyl, (Ci-C7)-Haloalkoxy-(Ci-C7)-alkyl, (C1-C7)- Alkoxy-(CrC7)-haloalkyl, (Ci-C7)-Haloalkoxy-(CrC7)-haloalkyl, (C1-C7)- Alkylthio-(d-C7)-alkyl, (Ci-C7)-Haloalkylthio-(Ci-C7)-alkyl steht, Q-4 Q-5 and Q-6 where R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 17 , R 18 , R 19 , R 20 , R 22 , R 23 , R 24 , R 25 , R 26 , R 28 , R 29 and R 30 and A 1 to A 9 each have the meaning according to the following definitions and wherein the arrow for a bond to the respective group CR 6 in the general formula (I), for (Ci -C 7 ) -alkyl, (C 3 -C 7 ) -cycloalkyl, (C 4 -C 7 ) -cycloalkenyl, (C 2 -C 7 ) -alkenyl, (C 2 -C 7 ) -alkynyl, (C 2 -C 7) alkenyl (Ci-C7) alkyl, (C 2 -C 7) alkynyl (Ci-C7) alkyl, (Ci-C7) alkoxy (Ci-C 7) alkyl, hydroxy (Ci-C7) alkyl, (Ci-C7) haloalkyl, (C2-C7) - haloalkenyl, (C 2 -C 7) haloalkynyl, (Ci-C7) haloalkoxy (Ci-C7) alkyl, (C1-C7) - alkoxy (-C 7) haloalkyl, (Ci-C7) haloalkoxy (-C 7) haloalkyl, (C1-C7) - (alkylthio dC 7 ) -alkyl, (C 1 -C 7 ) -haloalkylthio (C 1 -C 7 ) -alkyl,
R3 und R4 unabhängig voneinander für Wasserstoff, Halogen, (Ci-C7)-Alkyl, R 3 and R 4 independently of one another represent hydrogen, halogen, (C 1 -C 7 ) -alkyl,
(C3-C7)-Cycloalkyl, (C4-C7)-Cycloalkenyl, (C2-C7)-Alkenyl, (C2-C7)-Alkinyl, (C2-C7)-Alkenyl-(Ci-C7)-alkyl, (C2-C7)-Alkinyl-(CrC7)-alkyl, (d-C7)-Alkoxy- (Ci-C7)-alkyl, Hydroxy-(d-C7)-alkyl, (Ci-C7)-Haloalkyl, (C2-C7)-Haloalkenyl, (C2-C7)-Haloalkinyl, (Ci-C7)-Haloalkoxy-(Ci-C7)-alkyl, (Ci-C7)-Alkoxy-(Ci-C7)- haloalkyl, (Ci-C7)-Haloalkoxy-(Ci-C7)-haloalkyl, (Ci-C7)-Alkylthio-(Ci-C7)-alkyl, (Ci-C7)-Haloalkylthio-(Ci-C7)-alkyl stehen, für Hydroxy, (Ci-C7)-Alkoxy, Aryloxy, (C3-C7)-Cycloalkyloxy, (C2-C7)-Alkenyloxy, (C2-C7)-Alkenyl-(Ci-C7)-alkyloxy, (Ci-C7)-Alkoxy-(d-C7)-alkyloxy, (C1-C7)- Alkylcarbonyloxy, Arylcarbonyloxy, Heteroarylcarbonyloxy, (C3-C7)- Cycloalkylcarbonyloxy, (d-C7)-Alkoxycarbonyloxy, (C2-C7)- Alkenyloxycarbonyloxy, Aryloxy-(Ci-C7)-alkyloxy, Aryl-(d-C7)-alkyloxy, (C1-C7)- Alkoxy-(Ci-C7)-alkoxy-(Ci-C7)-alkyloxy, (Ci-C7)-Alkylthio-(Ci-C7)-alkyloxy, Tris[(Ci-C7)-alkyl]silyloxy, (Ci-C7)-Alkyl-Bis[(Ci-C7)-alkyl]silyloxy, (Ci-C7)-Alkyl- bis(Aryl)silyloxy, Ary!-bis[(Ci-C7)— aikyljsilyioxy, Cycloalkyl-bis[(Ci-C7)- alkyl]silyloxy, Halo-bis[(Ci-C7)-alkyl]silyloxy, Tris[(Ci-C7)-alkyl]silyl-(Ci-C7)- alkoxy-(Ci-C7)-alkyloxy, steht, für (C1-C7)- Alkylsulfonylaminocarbonyl, (C3-C7)-(C 3 -C 7 ) -cycloalkyl, (C 4 -C 7 ) -cycloalkenyl, (C 2 -C 7 ) -alkenyl, (C 2 -C 7 ) -alkynyl, (C 2 -C 7 ) -alkenyl- (Ci-C7) alkyl, (C 2 -C 7) alkynyl (-C 7) alkyl, (dC 7) alkoxy (Ci-C7) alkyl, hydroxy (dC 7) alkyl , (Ci-C7) haloalkyl, (C 2 -C 7) haloalkenyl, (C 2 -C 7) haloalkynyl, (Ci-C7) haloalkoxy (Ci-C7) alkyl, (C -C 7) alkoxy (Ci-C7) - haloalkyl, (Ci-C7) haloalkoxy (Ci-C7) haloalkyl, (Ci-C7) -alkylthio (Ci-C 7) - alkyl, (Ci-C 7) are -Haloalkylthio-, hydroxy, (Ci-C7) alkoxy, aryloxy, (C3-C7) cycloalkyloxy, (C 2 (Ci-C7) alkyl -C 7 ) alkenyloxy, (C 2 -C 7) alkenyl (Ci-C7) alkyloxy, (Ci-C7) alkoxy (dC 7) alkyloxy, (C1-C7) - alkylcarbonyloxy, arylcarbonyloxy, heteroarylcarbonyloxy , (C 3 -C 7) -cycloalkylcarbonyloxy, (C 1 -C 4) -alkoxycarbonyloxy, (C 2 -C 7) -alkenyloxycarbonyloxy, aryloxy- (C 1 -C 7) -alkyloxy, aryl- (C 1 -C 7) -alkyloxy, (C 1 -C 7) Alkoxy- (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyloxy, (C 1 -C 7 ) -alkylthio (C 1 -C 7 ) -alkyloxy, tris [(C 1 -C 7 ) -alkyl] silyloxy, (Ci-C7) alkyl- Bis [(C 1 -C 7 ) -alkyl] silyloxy, (C 1 -C 7 ) -alkyl bis (aryl) silyloxy, aryl-bis [(C 1 -C 7 ) -alkylsilyloxy, cycloalkyl-bis [(Ci-C 7 ) -alkyl] silyloxy, halo-bis [(C 1 -C 7 ) -alkyl] silyloxy, tris [(C 1 -C 7 ) -alkyl] silyl- (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) - alkyloxy, represents (C 1 -C 7) -alkylsulfonylaminocarbonyl, (C 3 -C 7) -
Cycloalkylsulfonylaminocarbonyl, Hydroxycarbonyl, (Ci-C7)-Alkoxycarbonyl,
(C3-C7)-Cycloalkoxycarbonyl, (C3-C7)-Cycloalkyl-(Ci-C7)-alkoxycarbonyl, Aryloxycarbonyl, Aryl-(d-C7)-alkoxycarbonyl, (C2-C7)-Alkenyloxycarbonyl, (C2-C7)-Alkinyloxycarbonyl, (Ci-C7)-Haloalkyloxycarbonyl, (Ci-C7)-Alkoxy- (Ci-C7)-alkoxycarbonyl, (C2-C7)-Alkenyloxy-(Ci-C7)-alkoxycarbonyl, (C1-C7)- Alkylamino-(CrC7)-alkoxycarbonyl, Tris[(CrC7)-alkyl]silyloxy-(Ci-C7)- alkoxycarbonyl, Bis[(Ci-C7)-Alkyl]amino-(Ci-C7)-alkoxycarbonyl, (C1-C7)- Alkyl[(Ci-C7)-alky!jamino-(Ci-C7)-alkoxycarbonyl, Cyano-(Ci-C7)- alkoxycarbonyl, Heterocyclyl-N-(Ci-C7)-alkoxycarbonyl, Heteroaryloxycarbonyl, Heteroaryl-(Ci-C7)-alkoxycarbonyl, Heterocyclyl-(Ci-C7)-alkoxycarbonyl, Heterocyclyloxycarbonyl, (C2-C7)-Alkenyl-(Ci-C7)-alkoxycarbonyl, (C2-C7)- Alkinyl-(Ci-C7)-alkoxycarbonyl, Aryl-(C2-C7)-alkinyloxycarbonyl, Aryl-(C2-C7)- alkenyloxycarbonyL Aminocarbonyl, (Ci-C7)-Alkylaminocarbonyl, Bis[(d-C7)- alkyl]aminocarbonyl, (Ci-C7)-Alkyl[(Ci-C7)-Alkyl]aminocarbonyl, (C1-C7)- Alkyl[(Ci-C7)-Alkoxy]aminocarbonyl, (C2-C7)-Alkenylaminocarbonyl, (C3-C7)- Cycloalkylaminocarbonyl, Arylaminocarbonyl, Aryl-(Ci-C7)-alkylaminocarbonyl, Heteroaryl-(Ci-C7)-alkylaminocarbonyl, Cyano-(Ci-C7)-alkylaminocarbonyl, (Ci-C7)-Haloalkylaminocarbonyl, (C2-C7)-Alkinyl-(Ci-C7)-alkylaminocarbonyl, (Ci-C7)-Alkoxycarbonylaminocarbonyl, Aryl-(Ci-C7)- alkoxycarbonylaminocarbonyl, Hydroxycarbonyl-(Ci-C7)-alkyl, (C1-C7)- Alkoxycarbonyl-(Ci-C7)-alkyl, (C3-C7)-Cycloalkoxycarbonyl-(Ci-C7)-alkyl, (C3-C7)-Cycloalkyl-(Ci-C7)-alkoxycarbonyl-(Ci-C7)-alkyl, (C2-C7)- Alkenyloxycarbonyl-(CrC7)-alkyl, Aryl-(Ci-C7)-alkoxycarbonyl-(Ci-C7)-alkyl, (Ci-C7)-Alkylaminocarbonyl-(Ci-C7)-alkyl, Aminocarbonyl-(Ci-C7)-alkyl, Cycloalkylsulfonylaminocarbonyl, hydroxycarbonyl, (C 1 -C 7) -alkoxycarbonyl, (C3-C7) -cycloalkoxycarbonyl, (C3-C7) -cycloalkyl- (Ci-C7) -alkoxycarbonyl, aryloxycarbonyl, aryl- (d-C7) -alkoxycarbonyl, (C2-C7) -alkenyloxycarbonyl, (C2-C7) - Alkynyloxycarbonyl, (C 1 -C 7) -haloalkyloxycarbonyl, (C 1 -C 7) -alkoxy- (C 1 -C 7) -alkoxycarbonyl, (C 2 -C 7) -alkenyloxy- (C 1 -C 7) -alkoxycarbonyl, (C 1 -C 7) -alkylamino (C 1 -C 7) -alkoxycarbonyl, tris [(C 1 -C 7) -alkyl] silyloxy- (C 1 -C 7) -alkoxycarbonyl, bis [(C 1 -C 7) -alkyl] amino- (C 1 -C 7) -alkoxycarbonyl, (C 1 -C 7) - Alkyl [(C 1 -C 7 ) -alkyl] -amino (C 1 -C 7 ) -alkoxycarbonyl, cyano- (C 1 -C 7 ) -alkoxycarbonyl, heterocyclyl-N- (C 1 -C 7 ) -alkoxycarbonyl, heteroaryloxycarbonyl, heteroaryl- C 1 -C 7) -alkoxycarbonyl, heterocyclyl- (C 1 -C 7) -alkoxycarbonyl, heterocyclyloxycarbonyl, (C 2 -C 7) -alkenyl- (C 1 -C 7) -alkoxycarbonyl, (C 2 -C 7) -alkynyl- (C 1 -C 7) -alkoxycarbonyl , Aryl- (C 2 -C 7) -alkynyloxycarbonyl, aryl- (C 2 -C 7) -alkenyloxycarbonyL-aminocarbonyl, (C 1 -C 7) -alkylaminocarbonyl, bis [(C 1 -C 7) -alkyl] -aminocarbonyl, (C 1 -C 7) -alkyl [ (C 1 -C 7) -alkyl] aminocarbonyl, (C 1 -C 7) -alkyl [(C 1 -C 7) -alkoxy] -aminocarbonyl, (C 2 -C 4) 7) alkenylaminocarbonyl, (C 3 -C 7) -cycloalkylaminocarbonyl, arylaminocarbonyl, aryl- (C 1 -C 7) -alkylaminocarbonyl, heteroaryl- (C 1 -C 7) -alkylaminocarbonyl, cyano- (C 1 -C 7) -alkylaminocarbonyl, (C 1 -C 7) Haloalkylaminocarbonyl, (C 2 -C 7) -alkynyl- (C 1 -C 7) -alkylaminocarbonyl, (C 1 -C 7) -alkoxycarbonylaminocarbonyl, aryl- (C 1 -C 7) -alkoxycarbonylaminocarbonyl, hydroxycarbonyl- (C 1 -C 7) -alkyl, C7) - alkoxycarbonyl- (C 1 -C 7 ) -alkyl, (C 3 -C 7 ) -cycloalkoxycarbonyl- (C 1 -C 7 ) -alkyl, (C 3 -C 7 ) -cycloalkyl- (C 1 -C 7 ) -alkoxycarbonyl- (C 1 -C 7 -alkyl) ) -alkyl, (C 2 -C 7) -alkenyloxycarbonyl- (C 1 -C 7) -alkyl, aryl- (C 1 -C 7) -alkoxycarbonyl- (C 1 -C 7) -alkyl, (C 1 -C 7) -alkylaminocarbonyl- (C 1 -C 7) - alkyl, aminocarbonyl- (C 1 -C 7) -alkyl,
Bis[(Ci-C7)-alkyl]aminocarbonyl-(Ci-C7)-alkyl, (C3-C7)-Cycloalkylaminocarbonyl- (Ci-C7)-alkyl, Aryl-(Ci-C7)-alkylaminocarbonyl-(Ci-C7)-alkyl, Heteroaryl-(Ci-C7)- alkylaminocarbonyl-(Ci-C7)-alkyl, Cyano-(Ci-C7)-alkylaminocarbonyl-(Ci-C7)- alkyl, (Ci-C7)-Haloalkylaminocarbonyl-(Ci-C7)-alkyl, (C2-C7)-Alkinyl-(Ci-C7)- alkylaminocarbonyl-(Ci-C7)-alkyl, (C3-C7)-Cycloalkyl-(Ci-C7)- alkylaminocarbonyl-(Ci-C7)-alkyl, (Ci-C7)-Alkoxycarbonylaminocarbonyl- (Ci-C7)-alkyl, Aryl-(Ci-C7)-alkoxycarbonylaminocarbonyl-(Ci-C7)-alkyl, (C1-C7)- Alkoxycarbonyl-(Ci-C7)-alkylaminocarbonyl, Hydroxycarbonyl-(Ci-C7)- alkylaminocarbonyl, Aryl-(Ci-C7)-alkoxycarbonyl-(Ci-C7)-alkylaminocarbonyl, Aminocarbonyl-(Ci-C7)-alkylaminocarbonyl, (Ci-C7)-Alkylaminocarbonyl- (Ci-C7)-alkylaminocarbonyl,
(C3-C7)-Cycloalkylaminocarbonyl-(Ci-C7)-alkylaminocarbonyl, (C3-C7)- Cycloalkyl-(Ci-C7)-alkylaminocarbonyl, Aminosulfonyl, (Ci-Ce)-Alkoxycarbonyl- heterocyclyl-N-carbonyl, (Ci-C8)-Alkoxycarbonyl-(Ci-C8)-alkyl- heterocyclylidenaminocarbonyl, (Ci-C8)-Alkoxycarbonylheterocyclyliden-(d-C8)- alkylaminocarbonyl (Ci-C8)-Alkoxycarbonyl-(Ci-C8)-Alkyl((d-C8)- alkyl)aminocarbonyl, (Ci-C8)-Alkoxycarbonyl-(C:3-C8)- cycloalkylidenaminocarbonyl, Heterocyclyl-N-carbonyl, (Ci-C7)-Alkoxy-(d-C7)- alkylaminocarbonyi, (C; C7)-Cycloalkyl-(Ci-C7)-alkylaminocarbonyl-(Ci-C7)- alkyl, (C3-C7)-Cycloalkyl-(Ci-C7)-alkylaminocarbonyl-(Ci-C7)- alkylaminocarbonyl, (C2-C7)-Alkenyl-(Ci-C7)-alkylaminocarbonyl, (C2-C7)- Alkenylaminocarbonyl-(Ci-C7)-alkyl, (C2-C7)-Alkenyl-(Ci-C7)- alkylaminocarbonyl-(Ci-C7)-alkyl, (CrC7)-Alkylcarbonyl, (C3-C7)- Cycloalkylcarbonyl, ArylcarbonyL Formyl, Hydroxyiminomethyl, Bis [(Ci-C7) alkyl] aminocarbonyl (Ci-C7) alkyl, (C3-C7) -Cycloalkylaminocarbonyl- (Ci-C7) alkyl, aryl (Ci-C7) alkylaminocarbonyl (Ci C 7 ) -alkyl, heteroaryl- (C 1 -C 7 ) -alkylaminocarbonyl- (C 1 -C 7 ) -alkyl, cyano- (C 1 -C 7 ) -alkylaminocarbonyl- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -haloalkylaminocarbonyl - (Ci-C7) alkyl, (C2-C7) alkynyl (Ci-C7) - alkylaminocarbonyl (Ci-C7) alkyl, (C3-C7) -cycloalkyl- (Ci-C 7) alkylaminocarbonyl- (C 1 -C 7) -alkyl, (C 1 -C 7) -alkoxycarbonylaminocarbonyl- (C 1 -C 7) -alkyl, aryl- (C 1 -C 7) -alkoxycarbonylaminocarbonyl- (C 1 -C 7) -alkyl, (C 1 -C 7) Alkoxycarbonyl- (C 1 -C 7) -alkylaminocarbonyl, hydroxycarbonyl- (C 1 -C 7) -alkylaminocarbonyl, aryl- (C 1 -C 7) -alkoxycarbonyl- (C 1 -C 7) -alkylaminocarbonyl, aminocarbonyl- (C 1 -C 7) -alkylaminocarbonyl, ( C 1 -C 7) -alkylaminocarbonyl- (C 1 -C 7) -alkylaminocarbonyl, (C 3 -C 7) -cycloalkylaminocarbonyl- (C 1 -C 7) -alkylaminocarbonyl, (C 3 -C 7) -cycloalkyl- (C 1 -C 7) -alkylaminocarbonyl, aminosulfonyl, (C 1 -C 6) -alkoxycarbonyl-heterocyclyl-N-carbonyl, (Ci -C8) alkoxycarbonyl- (Ci-C8) -alkyl-heterocyclylidenaminocarbonyl, (Ci-C8) -alkoxycarbonylheterocyclyliden- (d-C8) -alkylaminocarbonyl (Ci-C8) -alkoxycarbonyl- (Ci-C8) -alkyl ((d- C 8) alkyl) aminocarbonyl, (C 1 -C 8) alkoxycarbonyl- (C 3 -C 8) -cycloalkylidene-aminocarbonyl, heterocyclyl-N-carbonyl, (C 1 -C 7) -alkoxy- (C 1 -C 7) -alkylaminocarbonyi, (C; C7) -cycloalkyl- (C 1 -C 7) -alkylaminocarbonyl- (C 1 -C 7) -alkyl, (C 3 -C 7) -cycloalkyl- (C 1 -C 7) -alkylaminocarbonyl- (C 1 -C 7) -alkylaminocarbonyl, (C 2 -C 7) ) alkenyl (Ci-C7) alkylaminocarbonyl, (C2-C7) - Alkenylaminocarbonyl- (Ci-C7) alkyl, (C2-C7) alkenyl (Ci-C7) - alkylaminocarbonyl (Ci C 7) alkyl, (C 1 -C 7) alkylcarbonyl, (C 3 -C 7) cycloalkylcarbonyl, arylcarbonyL formyl, hydroxyiminomethyl,
Aminoiminomethyl, (Ci-C7)-Alkoxyiminomethyl, (Ci-C7)-Alkylaminoiminomethyl, Bis[(Ci-C7)-alkyl]aminoiminomethyl, (C3-C7)-Cycloalkoxyiminomethyl, (C3-C7)- Cycloalkyl-(Ci-C7)-alkoximinomethyl, Aryloximinomethyl, Aryl-(Ci-C7)- alkoxyiminomethyl, Aryl-(Ci-C7)-alkylaminoiminomethyl, (C2-C7)- Alkenyloxyiminomethyl, ArylaminoiminomethyL Arylsulfonylaminoiminomethyl, Hydroxycarbonylheterocyclyl-(Ci-C7)-alkyl, (Ci-C7)-Alkoxycarbonylheterocyclyl- (Ci-C7)-alkyl, Hydroxycarbonyl-(C3-C7)-cycloalkyl-(Ci-C7)-alkyl, (C1-C7)- Alkoxycarbonyl-(C3-C7)-cycloalkyl-(CrC7)-alkyl, Hydroxyaminocarbonyl, (Ci-C7)-Alkoxyaminocarbonyl, Aryl-(Ci-C7)-alkoxyaminocarbonyl steht, Aminoiminomethyl, (C 1 -C 7) -alkoxyiminomethyl, (C 1 -C 7) -alkylaminoiminomethyl, bis [(C 1 -C 7) -alkyl] aminoiminomethyl, (C 3 -C 7) -cycloalkoxyiminomethyl, (C 3 -C 7) -cycloalkyl- (C 1 -C 7 ) -alkoximinomethyl, aryloximinomethyl, aryl- (C 1 -C 7) -alkoxyiminomethyl, aryl- (C 1 -C 7) -alkylaminoiminomethyl, (C 2 -C 7) -alkenyloxyiminomethyl, arylaminoiminomethyl, arylsulfonylaminoiminomethyl, hydroxycarbonylheterocyclyl- (C 1 -C 7) -alkyl, C7) -alkoxycarbonylheterocyclyl- (C 1 -C 7 ) -alkyl, hydroxycarbonyl- (C 3 -C 7 ) -cycloalkyl- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkoxycarbonyl- (C 3 -C 7 ) -cycloalkyl- ( C 1 -C 7) -alkyl, hydroxyaminocarbonyl, (C 1 -C 7) -alkoxyaminocarbonyl, aryl- (C 1 -C 7) -alkoxyaminocarbonyl,
R7, R8 , R9 und R10 unabhängig voneinander für Wasserstoff, Halogen, Nitro, Amino, Cyano, (Ci-C7)-Alkyl, Aryl, Heteroaryl, (C3-C7)-Cycloalkyl, (C4-C7)-Cycloalkenyl, (C2-C7)-Alkenyl, (C2-C7)-Alkinyl, (C2-C7)-Alkenyl-(Ci-C7)-alkyl, (C2-C7)-Alkinyl- (Ci-C7)-alkyl, Hydroxy, (Ci-C7)-Alkoxy, (Ci-C7)-Alkoxy-(Ci-C7)-alkoxy, (C1-C7)- Alkoxy-(Ci-C7)-alkyl, Hydroxy-(Ci-C7)-alkyl, (Ci-C7)-Haloalkoxy, (C1-C7)- Haloalkyl, (C2-C7)-Haloalkenyl, (C2-C7)-Haloalkinyl, (Ci-C7)-Haloalkoxy-(Ci-C7)- alkyl, (Ci-C7)-Alkoxy-(Ci-C7)-haloalkyl, (Ci-C7)-Haloalkoxy-(Ci-C7)-haloalkyl, Hydrothio, (CrC7)-Alkylthio, (Ci-C7)-Haloalkylthio. (Ci-C7)-Alkylthio-(Ci-C7)- alkyl, (Ci-C7)-Haloalkylthio-(Ci-C7)-alkyl, (Ci-C7)-Alkylamino, Bis[(Ci-C7)- alkyl]amino, (C2-C7)-Alkenylamino, (C3-C7)-Cycloalkylamino, (C1-C7)- Alkylcarbonylamino, (C3-C7)-Cycloalkylcarbonylamino, Arylcarbonylamino,
Heteroarylcarbonylamino, Formylamino, (Ci-C7)-Haloalkylcarbonylamino, (CrC7)-Alkoxycarbonylamino, (Ci-C7)-Alkylaminocarbonylamino, (C1-C7)- Alkyl[(Ci-C7)-Alkyl]aminocarbonylamino, (Ci-C7)-Alkylsulfonylamino, (C3-C7)- Cycloalkylsulfonylamino, Arylsulfonylamino, Hetarylsulfonylamino, Sulfonyl- (Ci-C7)-haloalkylamino, Amino-(Ci-C7)-alkylsulfonyl, Amino-(CrC7)- haloalkylsulfonyl, (Ci-C7)-Alkylaminosulfonyl, Bis[(Ci-C7)-alkyl]aminosulfonyl, (C3-C7)-Cycloalkylaminosulfonyl, (Ci-C7)-Haloalkylaminosulfonyl, R 7, R 8, R 9 and R 10 are independently hydrogen, halogen, nitro, amino, cyano, (Ci-C7) alkyl, aryl, heteroaryl, (C 3 -C 7) cycloalkyl, (C 4 -C 7 ) -cycloalkenyl, (C 2 -C 7 ) -alkenyl, (C 2 -C 7 ) -alkynyl, (C 2 -C 7 ) -alkenyl- (C 1 -C 7 ) -alkyl, (C 2 -) C 7 ) alkynyl (C 1 -C 7 ) -alkyl, hydroxy, (C 1 -C 7 ) -alkoxy, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkoxy, (C 1 -C 7 ) -alkoxy (C 1 -C 7 ) -alkyl, hydroxy- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -haloalkoxy, (C 1 -C 7 ) -haloalkyl, (C 2 -C 7 ) -haloalkenyl, (C 2 -C 7 ) -alkyl C 7) haloalkynyl, (Ci-C7) haloalkoxy (Ci-C7) - alkyl, (Ci-C7) alkoxy (Ci-C7) haloalkyl, (Ci-C7) haloalkoxy ( C 1 -C 7 ) -haloalkyl, hydrothio, (C 1 -C 7 ) -alkylthio, (C 1 -C 7 ) -haloalkylthio. (Ci-C7) -alkylthio (Ci-C 7) - alkyl, (Ci-C7) -Haloalkylthio- (Ci-C7) alkyl, (Ci-C7) alkylamino, bis [(Ci-C 7 ) alkyl] amino, (C 2 -C 7) -alkenylamino, (C 3 -C 7) -cycloalkylamino, (C 1 -C 7) -alkylcarbonylamino, (C 3 -C 7) -cycloalkylcarbonylamino, arylcarbonylamino, Heteroarylcarbonylamino, formylamino, (C 1 -C 7) -haloalkylcarbonylamino, (C 1 -C 7) -alkoxycarbonylamino, (C 1 -C 7) -alkylaminocarbonylamino, (C 1 -C 7) -alkyl [(C 1 -C 7) -alkyl] -aminocarbonylamino, (C 1 -C 7) - Alkylsulfonylamino, (C 3 -C 7) -cycloalkylsulfonylamino, arylsulfonylamino, hetarylsulfonylamino, sulfonyl- (C 1 -C 7) -haloalkylamino, amino- (C 1 -C 7) -alkylsulfonyl, amino- (C 1 -C 7) -haloalkylsulfonyl, (C 1 -C 7) -alkylaminosulfonyl, Bis [(C 1 -C 7) -alkyl] aminosulfonyl, (C 3 -C 7) -cycloalkylaminosulfonyl, (C 1 -C 7) -haloalkylaminosulfonyl,
Heteroarylaminosulfonyl, Arylaminosulfonyl, Aryl-(Ci-C7)-alkylaminosulfonyl, (Ci-C7)-Alkylsulfonyl, (C3-C7)-Cycloalkylsulfonyl, Arylsulfonyl, Hydroxycarbonyl, (Ci-C7)-Alkoxycarbonyl, (C3-C7)-Cycloalkoxycarbonyl, (C3-C7)-Cycloalkyl- (d-C7)-alkoxycarbonyl, Aryloxycarbonyl, Aryl-(d-C7)-alkoxycarbonyl, (C2-C7)- Alkenyloxycarbonyl, (C2-C7)-Alkinyloxycarbonyl, Aminocarbonyl, (C1-C7)- Alkylaminocarbonyl, Bis[(CrC7)-alkyl]aminocarbonyL (Ci-C7)-Alkyl[(Ci-C7)- Alkyljaminocarbonyl, (Ci-C7)-Alkyl[(CrC7)-Alkoxy]aminocarbonyl, (C2-C7)- Alkenylaminocarbonyl, (C3-C7)-Cycloalkylaminocarbonyl, Arylaminocarbonyl, Aryl-(Ci-C7)-alkylaminocarbonyl stehen, Heteroarylaminosulfonyl, arylaminosulfonyl, aryl- (C 1 -C 7) -alkylaminosulfonyl, (C 1 -C 7) -alkylsulfonyl, (C 3 -C 7) -cycloalkylsulfonyl, arylsulfonyl, hydroxycarbonyl, (C 1 -C 7) -alkoxycarbonyl, (C 3 -C 7) -cycloalkoxycarbonyl, (C 3 -C 7) -cycloalkyl- (C 1 -C 7) -alkoxycarbonyl, aryloxycarbonyl, aryl- (C 1 -C 7) -alkoxycarbonyl, (C 2 -C 7) -alkenyloxycarbonyl, (C 2 -C 7) -alkynyloxycarbonyl, aminocarbonyl, (C 1 -C 7 ) - Alkylaminocarbonyl, bis [(C 1 -C 7) -alkyl] aminocarbonyL (C 1 -C 7) -alkyl [(C 1 -C 7) -alkyl] aminocarbonyl, (C 1 -C 7) -alkyl [(C 1 -C 7) -alkoxy] -aminocarbonyl, (C 2 -C 7) Alkenylaminocarbonyl, (C 3 -C 7) -cycloalkylaminocarbonyl, arylaminocarbonyl, aryl- (C 1 -C 7) -alkylaminocarbonyl,
A1, A2, A3 und A4 gleich oder verschieden sind und unabhängig voneinander für NA 1 , A 2 , A 3 and A 4 are the same or different and are independently N
(Stickstoff) oder die Gruppierungen C-H, C-CH3, C-F, C-Cl, C-Br, C-l, C-OCF3, C-OCH3, C-CF3, C-CO2H, C-CO2CH3 stehen, wobei jedoch in keinem Fall mehr als zwei N-Atome benachbart sind, (Nitrogen) or the groupings CH, C-CH3, CF, C-Cl, are C-Br Cl, C-OCF3, C-OCH3, C-CF 3, C-CO2H, C-CO2CH3, but in no Case more than two N atoms are adjacent,
R11 und R12 unabhängig voneinander für Wasserstoff, Halogen, (Ci-C-7)-Alkyl, Aryl, Heteroaryl, Heterocyclyl, (C3-C7)-Cycloalkyli (C2-C7)-Alkenyl, (C2-C7)-Alkinyl, (CrC7)-Alkoxy, (Ci-C7)-Alkoxy-(Ci-C7)-alkyl, Aryloxy-(Ci-C7)-alkyl, (C1-C7)- Haloalkoxy, (CrC7)-Haloalkyl, (Ci-C7)-Haloalkoxy-(Ci-C7)-alkyl, (Ci-C7)-Alkoxy- (Ci-C7)-haloalkyl, (Ci-C7)-Haloalkoxy-(Ci-C7)-haloalkyl, (Ci-C7)-Alkylthio, R 11 and R 12 independently of one another represent hydrogen, halogen, (C 1 -C 7 ) -alkyl, aryl, heteroaryl, heterocyclyl, (C 3 -C 7 ) -cycloalkyl , (C 2 -C 7 ) -alkenyl, (C 2 -C 7) alkynyl, (-C 7) alkoxy, (Ci-C7) alkoxy (Ci-C7) alkyl, aryloxy (Ci-C7) alkyl, (C1-C7) - Haloalkoxy, (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -haloalkoxy- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) Haloalkoxy- (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -alkylthio,
(Ci-C7)-Haloalkylthio, (Ci-C7)-Alkylthio-(Ci-C7)-alkyl, Hydroxycarbonyl, (C1-C7)- Alkoxycarbonyl, (C3-C7)-Cycloalkoxycarbonyl, (C3-C7)-Cycloalkyl-(Ci-C7)- alkoxycarbonyl, Aryloxycarbonyl, Aryl-(Ci-C7)-alkoxycarbonyl, (C2-C7)- Alkenyloxycarbonyl, (C2-C7)-Alkinyloxycarbonyl, Aminocarbonyl, (C1-C7)- Alkylaminocarbonyl, Bis[(d-C7)-alkyl]aminocarbonyl, (Ci-C7)-Alkyi[(d-C7)- Alkyljaminocarbonyl, (Ci-C7)-Alkyl[(Ci-C7)-Alkoxy]aminocarbonyl, (C2-C7)-
Alkenylaminocarbonyl, (C3-C7)-Cycloalkylaminocarbonyl, Arylaminocarbonyl, Aryl-(Ci-C7)-alkylaminocarbonyl stehen, (C 1 -C 7 ) -haloalkylthio, (C 1 -C 7 ) -alkylthio (C 1 -C 7 ) -alkyl, hydroxycarbonyl, (C 1 -C 7 ) -alkoxycarbonyl, (C 3 -C 7 ) -cycloalkoxycarbonyl, (C 3 -C 7 ) - Cycloalkyl- (C 1 -C 7) -alkoxycarbonyl, aryloxycarbonyl, aryl- (C 1 -C 7) -alkoxycarbonyl, (C 2 -C 7) -alkenyloxycarbonyl, (C 2 -C 7) -alkynyloxycarbonyl, aminocarbonyl, (C 1 -C 7) -alkylaminocarbonyl, bis [ (C 1 -C 4) -alkyl] aminocarbonyl, (C 1 -C 7) -alkyi [(C 1 -C 7) -alkyl] aminocarbonyl, (C 1 -C 7) -alkyl [(C 1 -C 7) -alkoxy] -aminocarbonyl, (C 2 -C 7) - Alkenylaminocarbonyl, (C 3 -C 7) -cycloalkylaminocarbonyl, arylaminocarbonyl, aryl- (C 1 -C 7) -alkylaminocarbonyl,
A5 für S (Schwefel), O (Sauerstoff) oder die Gruppierungen N-H, N-CH3, N-CH2CH3, N- CH(CH3)2, N-C02t-Bu, N-Aryl, N-Heteroaryl, N-Heterocyclyl steht, A 5 for S (sulfur), O (oxygen) or the groupings NH, N-CH 3 , N-CH 2 CH 3 , N-CH (CH 3 ) 2 , N-CO 2 t-Bu, N-aryl, N-heteroaryl , N-heterocyclyl,
R13, R14, R17 und R18 unabhängig voneinander für Wasserstoff, (Ci-C-7)-Alkyl, Halogen, (C3-C7)-Cycloalkyl, Aryl, Heteroaryl, Heterocyclyl, (C2-C7)-Alkenyl, (C2-C7)- Alkenyl-(Ci-C7)-alkyl, Aryl-(Ci-C7)-alkyl, (Ci-C7)-Alkoxy, (Ci-C7)-Alkoxy-(Ci-C7)- alkoxy, (Ci-C7)-Alkoxy-(Ci-C7)-alkyl, Hydroxy, (Ci-C7)-Haloalkyl, (C1-C7)- Haloalkylthio stehen oder R 13 , R 14 , R 17 and R 18 are each independently hydrogen, (Ci-C-7) -alkyl, halogen, (C 3 -C 7 ) -cycloalkyl, aryl, heteroaryl, heterocyclyl, (C 2 -C 7 ) -Alkenyl, (C 2 -C 7 ) -alkenyl- (C 1 -C 7 ) -alkyl, aryl- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkoxy, (C 1 -C 7 ) -alkoxy (C 1 -C 7 ) -alkoxy, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, hydroxy, (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -haloalkylthio or
R13 und R17 mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls weiter substituierten 5 bis 7-gliedrigen Ring bilden, R 13 and R 17 with the atoms to which they are attached form a completely saturated or partially saturated, optionally further substituted 5 to 7-membered ring,
A6, A7 gleich oder verschieden sind und unabhängig voneinander für O (Sauerstoff), S (Schwefel), N-H, N-OCH3, N-CH3 oder die Gruppierung CR15R16 stehen, wobei jedoch in keinem Fall zwei N-, O- oder S-Atome benachbart sind, und wobei R15 und R16 in der Gruppierung CR15R16 jeweils gleiche oder verschiedene A 6 , A 7 are the same or different and independently of one another are O (oxygen), S (sulfur), NH, N-OCH 3, N-CH 3 or the group CR 15 R 16 , although in each case two N-, O or S atoms are adjacent, and wherein R 15 and R 16 in the group CR 15 R 16 are identical or different
Bedeutungen gemäß der nachstehenden Definition haben und Have meanings as defined below and
R15 und R16 unabhängig voneinander für Wasserstoff, Halogen, (d-C7)-Alkyl, Aryl, Heteroaryl, Heterocyclyl, (C3-C7)-Cycloalkyl, (C2-C7)-Alkenyl, (Ci-C7)-Alkoxy, (Ci-C7)-Alkoxy-(Ci-C7)-alkyl, Aryloxy-(Ci-C7)-alkyl, (Ci-C7)-Haloalkoxy, (C1-C7)- Haloalkyl, (Ci-C7)-Haloalkoxy(Ci-C7)-alkyl, (Ci-C7)-Alkoxy-(Ci-C7)-haloalkyl, (Ci-C7)-Haloalkoxy-(Ci-C7)-haloalkyl, (Ci-C7)-Alkylthio, (Ci-C7)-Haloalkylthio, (Ci-C7)-Alkylthio-(Ci-C7)-alkyl, Hydroxycarbonyl, (Ci-C7)-Alkoxycarbonyl, R 15 and R 16 independently of one another represent hydrogen, halogen, (C 1 -C 7 ) -alkyl, aryl, heteroaryl, heterocyclyl, (C 3 -C 7 ) -cycloalkyl, (C 2 -C 7 ) -alkenyl, (Ci-C 7 ) -alkoxy, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, aryloxy- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -haloalkoxy, (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -haloalkoxy (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -haloalkoxy- (C 1 -C 7 ) - haloalkyl, (C 1 -C 7 ) -alkylthio, (C 1 -C 7 ) -haloalkylthio, (C 1 -C 7 ) -alkylthio (C 1 -C 7 ) -alkyl, hydroxycarbonyl, (C 1 -C 7 ) -alkoxycarbonyl,
(C3-C7)-Cycloalkoxycarbonyl, (C3-C7)-Cycloalkyl-(Ci-C7)-alkoxycarbonyl, Aryloxycarbonyl, Aryl-(Ci-C7)-alkoxycarbonyl, (C2-C7)-Alkenyloxycarbonyl, (C2-C7)-Alkinyloxycarbonyl, Aminocarbonyl, (Ci-C7)-Alkylaminocarbonyl, Bis[(CrC7)-alkyl]aminocarbonyl, (Ci-C7)-Alkyl[(CrC7)-Alkyl]aminocarbonyl, (Ci-C7)-Alkyl[(CrC7)-Alkoxy]aminocarbonyl, (C2-C7)-Alkenylaminocarbonyl, (C3-C7)-Cycloalkylaminocarbonyl, Arylaminocarbonyl, Aryl-(d-C7)-
alkylaminocarbonyl, Amino, (Ci-C7)-Alkylamino, (C3-C7)-Cycloalkylamino, Bis- [(CrC7)-Alkyl]amino stehen, (C 3 -C 7) -cycloalkoxycarbonyl, (C 3 -C 7) -cycloalkyl- (C 1 -C 7) -alkoxycarbonyl, aryloxycarbonyl, aryl- (C 1 -C 7) -alkoxycarbonyl, (C 2 -C 7) -alkenyloxycarbonyl, (C 2 -C 7) ) Alkynyloxycarbonyl, aminocarbonyl, (Ci-C7) -alkylaminocarbonyl, bis [(CrC7) -alkyl] aminocarbonyl, (Ci-C7) -alkyl [(CrC7) -alkyl] aminocarbonyl, (Ci-C7) -alkyl [(CrC7 ) -Alkoxy] aminocarbonyl, (C 2 -C 7) -alkenylaminocarbonyl, (C 3 -C 7) -cycloalkylaminocarbonyl, arylaminocarbonyl, aryl- (d-C 7) - alkylaminocarbonyl, amino, (C 1 -C 7 ) -alkylamino, (C 3 -C 7 ) -cycloalkylamino, bis [(C 1 -C 7) -alkyl] -amino,
R19, R20, R22 und R23 unabhängig voneinander für Wasserstoff, (Ci-C/)-Alkyl, Halogen, (C3-C7)-Cycloalkyl, Aryl, Heteroaryl, Heterocyclyl, (C2-C7)-Alkenyl, Aryl-(Ci-C7)- alkyl, (Ci-C7)-Alkoxy, (Ci-C7)-Alkoxy-(Ci-C7)-alkoxy, (Ci-C7)-Alkoxy-(Ci-C7)- alkyl, (d-C7)-Haloalkyl stehen, R 19 , R 20 , R 22 and R 23 independently of one another represent hydrogen, (C 1 -C 4 ) -alkyl, halogen, (C 3 -C 7 ) -cycloalkyl, aryl, heteroaryl, heterocyclyl, (C 2 -C 7 ) alkenyl, aryl (Ci-C7) - alkyl, (Ci-C7) alkoxy, (Ci-C7) alkoxy (Ci-C7) alkoxy, (Ci-C7) alkoxy (Ci-C7) - alkyl, (dC 7) -haloalkyl stand,
A8 für O (Sauerstoff), S (Schwefel), N-H, N-CH3, N-OCH3 oder die Gruppierung CHR21 steht und wobei R21 in der Gruppierung CHR21 die Bedeutung gemäß der nachstehenden Definition hat, A 8 is O (oxygen), S (sulfur), NH, N-CH 3 , N-OCH 3 or the moiety CHR 21 , and wherein R 21 in the moiety CHR 21 has the meaning as defined below,
R21 für Wasserstoff, Halogen, (Ci-C7)-Alkyl, Aryl, Heteroaryl, Heterocyclyl, (C3-C7)- Cycloalkyl, (C2-C7)-Alkenyl, (Ci-C7)-Alkoxy, (Ci-C7)-Alkoxy-(Ci-C7)-alkyl, Aryloxy-(Ci-C7)-alkyl, (Ci-C7)-Haloalkoxy, (d-C7)-Haloalkyl, (d-C7)-Alkoxy- (Ci-C7)-haloalkyl, (Ci-C7)-Haloalkoxy-(CrC7)-haloalkyl, (Ci-C7)-Alkylthio, R 21 is hydrogen, halogen, (Ci-C 7) alkyl, aryl, heteroaryl, heterocyclyl, (C3-C7) - cycloalkyl, (C 2 -C 7) alkenyl, (Ci-C7) alkoxy, ( Ci-C7) alkoxy (Ci-C7) alkyl, aryloxy (Ci-C7) alkyl, (Ci-C7) haloalkoxy, (dC 7) -haloalkyl, (dC 7) alkoxy (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -haloalkoxy- (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -alkylthio,
(Ci-C7)-Haloalkylthio, (Ci-C7)-Alkylthio-(Ci-C7)-alkyl, Hydroxycarbonyl, (C1-C7)- Alkoxycarbonyl, (C3-C7)-Cycloalkoxycarbonyl, Aryl-(Ci-C7)-alkoxycarbonyl, (C2-C7)-Alkenyloxycarbonyl, (C2-C7)-Alkinyloxycarbonyl, Aminocarbonyl, (Ci-C 7) haloalkylthio, (Ci-C7) -alkylthio (Ci-C 7) alkyl, hydroxycarbonyl, (C1-C7) - alkoxycarbonyl, (C 3 -C 7) cycloalkoxycarbonyl, aryl ( C 1 -C 7 ) -alkoxycarbonyl, (C 2 -C 7 ) -alkenyloxycarbonyl, (C 2 -C 7 ) -alkynyloxycarbonyl, aminocarbonyl,
(Ci-C7)-Alkylaminocarbonyl, Bis[(Ci-C7)-alkyl]aminocarbonyl, (C1-C7)- Alkyl[(Ci-C7)-Alkyl]aminocarbonyl, (Ci-C7)-Alkyl[(Ci-C7)-Alkoxy]aminocarbonyl, (C2-C7)-Alkenylaminocarbonyl, (C3-C7)-Cycloalkylaminocarbonyl, (C 1 -C 7 ) -alkylaminocarbonyl, bis [(C 1 -C 7 ) -alkyl] aminocarbonyl, (C 1 -C 7 ) -alkyl [(C 1 -C 7 ) -alkyl] aminocarbonyl, (C 1 -C 7 ) -alkyl [ (C 1 -C 7 ) -alkoxy] aminocarbonyl, (C 2 -C 7 ) -alkenylaminocarbonyl, (C 3 -C 7 ) -cycloalkylaminocarbonyl,
Arylaminocarbonyl, Aryl-(Ci-C7)-alkylaminocarbonyl, Amino, (Ci-C7)-Alkylamino, (C3-C7)-Cycloalkylamino, Bis[(Ci-C7)-Alkyl]amino steht, Arylaminocarbonyl, aryl- (C 1 -C 7 ) -alkylaminocarbonyl, amino, (C 1 -C 7 ) -alkylamino, (C 3 -C 7 ) -cycloalkylamino, bis [(C 1 -C 7 ) -alkyl] -amino,
R24, R25, R26, R28, R29 und R30 unabhängig voneinander für Wasserstoff, (Ci-C7)-Alkyl, Halogen, (C3-C7)-Cycloalkyl, Aryl, Heteroaryl, Heterocyclyl, (C2-C7)-Alkenyl, (Ci-C7)-Alkoxy, (Ci-C7)-Alkoxy-(Ci-C7)-alkoxy, (Ci-C7)-Alkoxy-(Ci-C7)-alkyl, (Ci-C7)-Haloalkyl, (Ci-C7)-Alkylthio, (Ci-C7)-Haloalkylthio stehen, R 24, R 25, R 26, R 28, R 29 and R 30 are independently hydrogen, (Ci-C7) alkyl, halogen, (C 3 -C 7) cycloalkyl, aryl, heteroaryl, heterocyclyl, ( C 2 -C 7 -alkenyl, (C 1 -C 7 ) -alkoxy, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkoxy, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) alkyl, (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -alkylthio, (C 1 -C 7 ) -haloalkylthio,
A9 für O (Sauerstoff), S (Schwefel), N-H, N-CH3, N-OCH3 oder die Gruppierung CHR27 steht und wobei R27 in der Gruppierung CHR27 die Bedeutung gemäß der nachstehenden Definition hat und
R27 für Wasserstoff, Halogen, (Ci-C-7)-Alkyl, Aryl, Heteroaryl, Heterocyclyl, (C3-C7)- Cycloalkyl, (C2-C7)-Alkenyl, (Ci-C7)-Alkoxy, (Ci-C7)-Alkoxy-(Ci-C7)-alkyl, Aryloxy-(Ci-C7)-alkyl, (Ci-C7)-Haloalkoxy, (Ci-C7)-Haloalkyl, (CrC7)-Alkylthio, (d-C7)-Haloalkylthio, Hydroxycarbonyl, (d-C7)-Alkoxycarbonyl, (C3-C7)- Cycloalkoxycarbonyl, Aryl-(CrC7)-alkoxycarbonyl, (C2-C7)-Alkenyloxycarbonyl,A 9 is O (oxygen), S (sulfur), NH, N-CH 3 , N -OCH 3 or the moiety CHR 27 and wherein R 27 in the moiety CHR 27 has the meaning as defined below and R 27 represents hydrogen, halogen, (C 1 -C 7 ) -alkyl, aryl, heteroaryl, heterocyclyl, (C 3 -C 7 ) -cycloalkyl, (C 2 -C 7 ) -alkenyl, (C 1 -C 7 ) -alkoxy, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, aryloxy- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -haloalkoxy, (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) Alkylthio, (d-C7) -haloalkylthio, hydroxycarbonyl, (C 1 -C 7) -alkoxycarbonyl, (C 3 -C 7) -cycloalkoxycarbonyl, aryl- (C 1 -C 7) -alkoxycarbonyl, (C 2 -C 7) -alkenyloxycarbonyl,
(C2-C7)-Alkinyloxycarbonyl, Aminocarbonyl, (Ci-C7)-Alkylaminocarbonyl, Bis[(Ci-C7)-alkyl]aminocarbonyl, (Ci-C7)-Alkyl[(CrC7)-Alkyl]aminocarbonyl, (Ci-C7)-Alkyl[(Ci-C7)-Alkoxy]aminocarbonyl, (C2-C7)-Alkenylaminocarbonyl, (C3-C7)-Cycloalkylaminocarbonyl, Arylaminocarbonyl, Aryl-(Ci-C7)- alkylaminocarbonyl, Amino, (Ci-C7)-Alkylamino, (C3-C7)-Cycloalkylamino,(C 2 -C 7) -Alkynyloxycarbonyl, aminocarbonyl, (C 1 -C 7) -alkylaminocarbonyl, bis [(C 1 -C 7) -alkyl] aminocarbonyl, (C 1 -C 7) -alkyl [(C 1 -C 7) -alkyl] aminocarbonyl, (C 1 -C 7 ) -Alkyl [(C 1 -C 7) -alkoxy] -aminocarbonyl, (C 2 -C 7) -alkenylaminocarbonyl, (C 3 -C 7) -cycloalkylaminocarbonyl, arylaminocarbonyl, aryl- (C 1 -C 7) -alkylaminocarbonyl, amino, (C 1 -C 7) - Alkylamino, (C 3 -C 7) -cycloalkylamino,
Bis[(Ci-C7)-Alkyl]amino steht. Bis [(Ci-C 7 ) alkyl] amino.
Bevorzugt sind Verbindungen der allgemeinen Formel (I), worin [X-Y] für die Gruppierung Preference is given to compounds of the general formula (I) in which [X-Y] is the grouping
[x-YF steht, [x-YF stands,
Q für die Gruppierungen Q-1 bis Q-6 Q for the groupings Q-1 to Q-6
Q-4 i Q-5 Und Q-6 steht, wobei R7, R8, R9, R10, R11, R12, R13, R14, R17, R18, R19, R20, R22, R23, R24, R25, R26, R28, R29 und R30 und A1 bis A9 jeweils die Bedeutung gemäß der
nachstehenden Definitionen haben und wobei der Pfeil für eine Bindung zur jeweiligen Gruppierung C-R6 in der allgemeinen Formel (I) steht, Q-4 Q-5 U i nd Q 6 where R 7, R 8, R 9, R 10, R 11, R 12, R 13, R 14, R 17, R 18, R 19, R 20 , R 22 , R 23 , R 24 , R 25 , R 26 , R 28 , R 29 and R 30 and A 1 to A 9 are each as defined in the have the following definitions and wherein the arrow for a bond to the respective grouping is CR 6 in the general formula (I),
R1 für (Ci-Cc)-Alkyl, (C3-C6)-Cycloalkyl, (C4-C6)-Cycloalkenyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (C2-C6)-Alkenyl-(Ci-C6)-alkyl, (C2-C6)-Alkinyl-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, Hydroxy-(Ci-C6)-alkyl, (Ci-C6)-Haloalkyl, (C2-C6)- Haloalkenyl, (C2-C6)-Haloalkinyl steht, R 1 is (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, (C 4 -C 6 ) -cycloalkenyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl , (C 2 -C 6) alkenyl (Ci-C 6) alkyl, (C2-C6) alkynyl (Ci-C 6) alkyl, (Ci-C 6) alkoxy (Ci- C 6) alkyl, hydroxy (Ci-C 6) alkyl, (Ci-C 6) -haloalkyl, (C 2 -C 6) - haloalkenyl, (C 2 -C 6) haloalkynyl group,
R2, R3 und R4 unabhängig voneinander für Wasserstoff, Fluor, (Ci-Cö)-Alkyl, (C3-Ce)- Cycloalkyl, (C4-Cc)-Cycloalkenyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (C2-C6)- Alkenyl-(CrC6)-alkyl, (C2-C6)-Alkinyl-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, Hydroxy-(Ci-C6)-alkyl, (Ci-C6)-Haloalkyl stehen, R 2, R 3 and R 4 independently of one another represent hydrogen, fluorine, (Ci-COE) alkyl, (C3-Ce) - cycloalkyl, (C 4 -C c) cycloalkenyl, (C 2 -C 6) alkenyl , (C 2 -C 6) -alkynyl, (C 2 -C 6) - alkenyl, (CrC 6) alkyl, (C 2 -C 6) alkynyl (Ci-C 6) alkyl, (Ci- C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, hydroxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkyl,
R5 für Hydroxy, (Ci-Ce)-Alkoxy, Aryloxy, (C3-C6)-Cycloalkyloxy, (C2-C6)-Alkenyloxy, (C2-C6)-Alkenyl-(Ci-C6)-alkyloxy, (Ci-C6)-Alkoxy-(Ci-C6)-alkyloxy, (Ci-C6)- Alkylcarbonyloxy, Arylcarbonyloxy, Heteroarylcarbonyloxy, (Ca-Ce)- Cycloalkylcarbonyloxy, (d-CeJ-Alkoxycarbonyloxy, (C2-Ce)- Alkenyloxycarbonyloxy, Aryloxy-(Ci-C6)-alkyloxy, Aryl-(Ci-C6)-alkyloxy, (Ci-Cr>)- Alkoxy-(Ci-C6)-alkoxy-(Ci-C6)-alkyloxy, (Ci-C6)-Alkylthio-(Ci-C6)-alkyloxy, Tris[(Ci-C6)-alkyl]silyloxy, (Ci-C6)-Alkyl-Bis[(Ci-C6)-alkyl]silyloxy, (Ci-Ce)-Alkyl- bis(Aryl)silyloxy, Aryl-bis[(Ci-Ce)— alkyl]silyloxy, Cycloalkyl-bis[(d-C6)- alkyl]silyloxy, Halo-bis[(Ci-C6)-alkyl]silyloxy, Ths[(Ci-C6)-alkyl]silyl-(Ci-C6)- alkoxy-(Ci-Co)-alkyloxy steht, R 5 is hydroxy, (Ci-Ce) alkoxy, aryloxy, (C3-C6) cycloalkyloxy, (C 2 -C 6) alkenyloxy, (C 2 -C 6) alkenyl (Ci-C 6) alkyloxy , (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyloxy, (C 1 -C 6 ) -alkylcarbonyloxy, arylcarbonyloxy, heteroarylcarbonyloxy, (Ca-Ce) -cycloalkylcarbonyloxy, (d-CeJ-alkoxycarbonyloxy, (C 2 -Ce) - alkenyloxycarbonyloxy, aryloxy- (Ci-C6) -alkyloxy, aryl- (Ci-C6) -alkyloxy, (Ci-Cr > ) - alkoxy- (Ci-C6) -alkoxy- (Ci-C 6 ) - alkyloxy, (C 1 -C 6 ) -alkylthio (C 1 -C 6 ) -alkyloxy, tris [(C 1 -C 6 ) -alkyl] silyloxy, (C 1 -C 6 ) -alkyl-bis [(C 1 -C 6 ) -alkyl ] silyloxy, (Ci-Ce) -alkyl bis (aryl) silyloxy, aryl-bis [(Ci-Ce) -alkyl] silyloxy, cycloalkyl-bis [(d-C6) -alkyl] silyloxy, halo-bis [( C 1 -C 6 ) -alkyl] silyloxy, Ths [(C 1 -C 6 ) -alkyl] silyl- (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyloxy,
R6 für (d-Ce)- Alkylsulfonylaminocarbonyl, (C3-Ce)-R 6 is (d-Ce) -alkylsulfonylaminocarbonyl, (C3-Ce) -
Cycloalkylsulfonylaminocarbonyl, Hydroxycarbonyl, (Ci-CeJ-Alkoxycarbonyl, (Ca-Ce Cycloalkoxycarbonyl, (C3-C6)-Cycloalkyl-(Ci-Cö)-alkoxycarbonyl, Aryloxycarbonyl, Aryl-(Ci-Cr>)-alkoxycarbonyl, (C2-C6)-Alkenyloxycarbonyl, (C2-C6)-Alkinyloxycarbonyl, (Ci-C6)-Haloalkyloxycarbonyl, (Ci-Cö)-Alkoxy- (d-C6)-alkoxycarbonyl, (C2-C6)-Alkenyloxy-(Ci-C6)-alkoxycarbonyl, (d-Ce)- Alkylamino-(Ci-C6)-alkoxycarbonyl, Ths[(Ci-C6)-alkyl]silyloxy-(Ci-Cc>)- alkoxycarbonyl, Bis[(Ci-Cö)-Alkyl]amino-(Ci-C6)-alkoxycarbonyl, (Ci-Ce)- Alkyl[(Ci-C6)-alkyl]amino-(Ci-C6)-alkoxycarbonyl, Cyano-(Ci-C6)- alkoxycarbonyl, Heterocyclyl-N-(Ci-C6)-alkoxycarbonyl, Heteroaryloxycarbonyl,
Heieroaryl-(Ci-C-6)-alkoxycarbonyl, Heierocyclyl-(Ci-C-6)-alkoxycarbonyl, Heterocyclyloxycarbonyl, (C2-C6)-Alkenyl-(CrC6)-alkoxycarbonyl, (C2-Ce)- Alkinyl-(Ci-C6)-alkoxycarbonyL Aryl-(C2-C6)-alkinyloxycarbonyl, Aryi-(C2-Cc,)- alkenyloxycarbonyl, Aminocarbonyl, (d-CeJ-Alkylaminocarbonyl, Bis[(d-C6)- alkyljaminocarbonyl, (Ci-C6)-Alkyl[(CrC6)-Alkyl]aminocarbonyl, (d-Ce)- Alkyl[(CrC6)-Alkoxy]aminocarbonyl, (C2-C6)-Alkenylaminocarbonyl, (CrCe)- Cycloalkylaminocarbonyl, Arylaminocarbonyi, Aryl-(CrC6)-alkylaminocarbonyl, Heteroaryl-(Ci-C6)-alkylaminocarbonyl, Cyano-(Ci-C6)-alkylaminocarbonyl, (Ci-Cö)-Haloalkylaminocarbonyl, (C2-C6)-Alkinyl-(Ci-C6)-alkylaminocarbonyl, (Ci-C6)-Alkoxycarbonylaminocarbonyl, Aryl-(Ci-C6)- alkoxycarbonylaminocarbonyl, Hydroxycarbonyl-(Ci-C6)-alkyl, (Ci-Ce)- Alkoxycarbonyl-(CrC6)-alkyl, (C3-C6)-Cycloalkoxycarbonyl-(CrC6)-alkyl, Cycloalkylsulfonylaminocarbonyl, hydroxycarbonyl, (Ci-CeJ-alkoxy, (Ca-Ce cycloalkoxycarbonyl, (C3-C6) cycloalkyl (Ci-COE) alkoxycarbonyl, aryloxycarbonyl, aryl (Ci-Cr>) -alkoxycarbonyl, (C 2 - C6) alkenyloxycarbonyl, (C 2 -C 6) -alkynyloxycarbonyl, (C 1 -C 6) -haloalkyloxycarbonyl, (C 1 -C 6) -alkoxy- (C 1 -C 6) -alkoxycarbonyl, (C 2 -C 6) -alkenyloxy- (C 1 -C 6) -alkyloxycarbonyl) C6) -alkoxycarbonyl, (d-Ce) -alkylamino- (Ci-C6) -alkoxycarbonyl, Ths [(Ci-C6) -alkyl] silyloxy- (Ci-Cc>) - alkoxycarbonyl, bis [(Ci-Cö) - Alkyl] amino- (C 1 -C 6) -alkoxycarbonyl, (C 1 -C 6) -alkyl [(C 1 -C 6) -alkyl] amino- (C 1 -C 6) -alkoxycarbonyl, cyano- (C 1 -C 6) -alkoxycarbonyl, heterocyclyl- N- (C 1 -C 6) alkoxycarbonyl, heteroaryloxycarbonyl, Heieroaryl- (Ci-C-6) alkoxycarbonyl, Heierocyclyl- (Ci-C-6) alkoxycarbonyl, heterocyclyloxycarbonyl, (C2-C6) alkenyl (CrC6) alkoxycarbonyl, (C2-Ce) alkynyl (Ci -C6) alkoxycarbonyL aryl- (C2-C6) -alkynyloxycarbonyl, aryl- (C2-Cc,) -alkenyloxycarbonyl, aminocarbonyl, (d-CeJ-alkylaminocarbonyl, bis [(d-C6) -alkyl-aminocarbonyl, (Ci-C6) Alkyl [(CrC6) alkyl] aminocarbonyl, (d-Ce) alkyl [(CrC6) alkoxy] aminocarbonyl, (C2-C6) alkenylaminocarbonyl, (CrCe) -cycloalkylaminocarbonyl, arylaminocarbonyi, aryl- (CrC6) -alkylaminocarbonyl , Heteroaryl- (C 1 -C 6) -alkylaminocarbonyl, cyano- (C 1 -C 6) -alkylaminocarbonyl, (C 1 -C 6) -haloalkylaminocarbonyl, (C 2 -C 6) -alkynyl- (C 1 -C 6) -alkylaminocarbonyl, (C 1 -C 6) Alkoxycarbonylaminocarbonyl, aryl- (Ci-C6) -alkoxycarbonylaminocarbonyl, hydroxycarbonyl- (Ci-C6) -alkyl, (Ci-Ce) - alkoxycarbonyl- (CrC6) -alkyl, (C3-C6) -cycloalkoxycarbonyl- (CrC6) -alkyl .
(C3-C6)-Cycloalkyl-(Ci-C6)-alkoxycarbonyl-(Ci-C6)-alkyl, (C2-C6)- Alkenyloxycarbonyl-(Ci-Cö)-alkyl, Aryl-(Ci-C6)-alkoxycarbonyl-(CrC6)-alkyl, (Ci-C6)-Alkylaminocarbonyl-(Ci-C6)-alkyl, Aminocarbonyl-(Ci-C6)-alkyl, (C3-C6) cycloalkyl (Ci-C6) alkoxycarbonyl (Ci-C 6) alkyl, (C 2 -C 6) - alkenyloxycarbonyl (Ci-COE) alkyl, aryl (Ci-C6) alkoxycarbonyl- (C 1 -C 6) -alkyl, (C 1 -C 6) -alkylaminocarbonyl- (C 1 -C 6) -alkyl, aminocarbonyl- (C 1 -C 6) -alkyl,
Bis[(Ci-C6)-alkyl]aminocarbonyl-(Ci-C6)-alkyl, (C3-C6)-Cycloalkylaminocarbonyl- (CrC6)-alkyl, Aryl-(Ci-C6)-alkylaminocarbonyl-(Ci-C6)-alkyl, Heteroaryl-(CrC6)- alkylaminocarbonyl-(Ci-C6)-alkyl, Cyano-(Ci-C6)-alkylaminocarbonyl-(Ci-C6)- alkyl, (Ci-C6)-Haloalkylaminocarbonyl-(Ci-C6)-alkyl, (C2-C6)-Alkinyl-(Ci-C6)- alkylaminocarbonyl-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl-(Ci-C6)- alkylaminocarbonyl-(CrC6)-alkyl, (Ci-Cc>)-Alkoxycarbonylaminocarbonyl- (Ci-C6)-alkyl, Aryl-(Ci-C6)-alkoxycarbonylaminocarbonyl-(Ci-C6)-alkyl, (Ci-Ce)- Alkoxycarbonyl-(Ci-C6)-alkylaminocarbonyl, Hydroxycarbonyl-(d-C6)- alkylaminocarbonyl, Aryl-(CrC6)-alkoxycarbonyl-(Ci-C6)-alkylaminocarbonyl, Aminosulfonyl, (Ci-CeJ-Alkoxycarbonyl-heterocyclyl-N-carbonyl, (d-Ce)- Alkoxycarbonyl-(Ci-C6)-alkyl-heterocyclylidenaminocarbonyl, (d-Ce)- Alkoxycarbonylheterocyclyliden-(Ci-C6)-alkylaminocarbonyl (Ci-Ce)- Alkoxycarbonyl-(Ci-C6)-Alkyl((Ci-C6)-alkyl)aminocarbonyl, (Ci-Ce)- Alkoxycarbonyl-(C3-C6)-cycloalkylidenaminocarbonyl, Heterocyclyl-N-carbonyl, (Ci-C6)-Alkoxy-(CrC6)-alkylaminocarbonyl, Aminocarbonyl-(Ci-C6)- alkylaminocarbonyl, (Ci-C6)-Alkylaminocarbonyl-(Ci-C6)-alkylaminocarbonyl, (C3-C6)-Cycloalkylaminocarbonyl-(Ci-C6)-alkylaminocarbonyl, (Cs-Ce)- Cycloalkyl-(CrC6)-alkylaminocarbonyl, (C3-C6)-Cycloalkyl-(Ci-C6)- alkylaminocarbonyl-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-
alkylaminocarbonyl-(Ci-C6)-alkylaminocarbonyl, (C2-C6)-Alkenyl-(Ci-C-6)- alkylaminocarbonyl, (C2-C6)-Alkenylaminocarbonyl-(Ci-C6)-alkyl, (C2-C6)- Alkenyl-(Ci-C6)-alkylaminocarbonyl-(Ci-C6)-alkyl, (Ci-C6)-Alkylcarbonyl, (C3-C6)- Cycloalkylcarbonyl, Arylcarbonyl, Formyl, Hydroxyiminomethyl, Bis [(Ci-C6) -alkyl] aminocarbonyl- (Ci-C6) -alkyl, (C3-C6) -cycloalkylaminocarbonyl- (CrC 6 ) -alkyl, aryl- (Ci-C 6 ) -alkylaminocarbonyl- (Ci-C6 ) alkyl, heteroaryl (CrC 6) - alkylaminocarbonyl (Ci-C6) alkyl, cyano (Ci-C6) alkylaminocarbonyl (Ci-C6) - alkyl, (Ci-C 6) -Haloalkylaminocarbonyl- (C C6) alkyl, (C 2 -C 6) alkynyl (Ci-C6) - alkylaminocarbonyl (Ci-C 6) alkyl, (C 3 -C 6) -cycloalkyl- (Ci-C6) - alkylaminocarbonyl - (CRC6) alkyl, (Ci-Cc>) -Alkoxycarbonylaminocarbonyl- (Ci-C6) alkyl, aryl (Ci-C6) -alkoxycarbonylaminocarbonyl- (Ci-C6) alkyl, (Ci-Ce) - alkoxycarbonyl (C 1 -C 6) -alkylaminocarbonyl, hydroxycarbonyl- (C 1 -C 6) -alkylaminocarbonyl, aryl- (C 1 -C 6) -alkoxycarbonyl- (C 1 -C 6) -alkylaminocarbonyl, aminosulfonyl, (C 1 -C 6 -alkoxycarbonyl-heterocyclyl-N-carbonyl, ( d-Ce) - alkoxycarbonyl- (Ci-C6) -alkyl-heterocyclylidenaminocarbonyl, (d-Ce) - Alkoxycarbonylheterocyclyliden- (Ci-C6) -alkylaminocarbonyl (Ci-Ce) - Alkoxycarbonyl- (Ci-C6) -alkyl ((Ci -C 6) -alkyl) aminocarbonyl, (C 1 -C 6) -alkoxycarbonyl- (C 3 -C 6) -cycloalkylidena minocarbonyl, heterocyclyl-N-carbonyl, (C 1 -C 6) -alkoxy- (C 1 -C 6) -alkylaminocarbonyl, aminocarbonyl- (C 1 -C 6) -alkylaminocarbonyl, (C 1 -C 6) -alkylaminocarbonyl- (C 1 -C 6) -alkylaminocarbonyl, (C3 -C 6) -cycloalkylaminocarbonyl- (C 1 -C 6) -alkylaminocarbonyl, (Cs-Ce) -cycloalkyl- (C 1 -C 6) -alkylaminocarbonyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkylaminocarbonyl- (C 1 -C 6 ) alkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) - alkylaminocarbonyl- (C 1 -C 6) -alkylaminocarbonyl, (C 2 -C 6) -alkenyl- (C 1 -C 6) -alkylaminocarbonyl, (C 2 -C 6) -alkenylaminocarbonyl- (C 1 -C 6) -alkyl, (C 2 -C 6) alkenyl (Ci-C6) alkylaminocarbonyl (Ci-C 6) alkyl, (Ci-C 6) alkylcarbonyl, (C 3 -C 6) - cycloalkylcarbonyl, arylcarbonyl, formyl, hydroxyiminomethyl,
Aminoiminomethyl, (CrCeJ-Alkoxyiminomethyl, (Ci-C6)-Alkyiaminoiminomethyl, Bis[(Ci-C6)-alkyl]aminoiminomethyl, (Ca-CeJ-Cycloalkoxyiminomethyl, (Ca-Ce)- Cycloalkyl-(Ci-C6)-alkoximinomethyl, Aryloximinomethyl, Aryl-(Ci-C6)- alkoxyiminomethyl, Aryl-(Ci-C6)-alkylaminoiminomethyl, (C2-C6)- Alkenyloxyiminomethyl, Aryiaminoiminomethyi, Arylsulfonylaminoiminomethyl, Hydroxyaminocarbonyl, (Ci-Cf,)-Alkoxyaminocarbonyl, Aryl-(Ci-Ce)- alkoxyaminocarbonyl steht, Aminoiminomethyl, (CrCeJ-alkoxyiminomethyl, (C 1 -C 6) -alkyiaminoiminomethyl, bis [(C 1 -C 6) -alkyl] aminoiminomethyl, (Ca-CeJ-cycloalkoxyiminomethyl, (Ca-Ce) -cycloalkyl- (C 1 -C 6) -alkoximinomethyl, Aryloximinomethyl, aryl- (C 1 -C 6) -alkoxyiminomethyl, aryl- (C 1 -C 6) -alkylaminoiminomethyl, (C 2 -C 6) -alkenyloxyiminomethyl, aryiaminoiminomethyl, arylsulfonylaminoiminomethyl, hydroxyaminocarbonyl, (C 1 -Cf,) -alkoxyaminocarbonyl, aryl- Ce) - alkoxyaminocarbonyl,
R7, R8 , R9 und R10 unabhängig voneinander für Wasserstoff, Fluor, Chlor, Brom, lod, Nitro, Amino, Cyano, (d-CeJ-Alkyl, gegebenenfalls substituiertes Phenyl, Heteroaryl, (C3-C6)-Cycloalkyl. (C4-C6)-Cycloalkenyl, (C2-C6)-Alkenyl, (C2-C6)- Alkinyl, (C2-C6)-Alkenyl-(Ci-C6)-alkyl, (C2-C6)-Alkinyl-(Ci-C6)-alkyl, Hydroxy, (Ci-C6)-Alkoxy, (Ci-C6)-Alkoxy-(Ci-C6)-alkoxy, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, Hydroxy-(Ci-C6)-alkyl, (Ci-Ce)-Haloalkoxy, (Ci-C6)-Haloalkyl, (C2-C6)- Haloalkenyl, (C2-C6)-Haloalkinyl, (Ci-C6)-Haloalkoxy-(Ci-C6)-alkyl, (Ci-Ce)- Alkoxy-(Ci-Ce)-haloalkyl, (Ci-C6)-Haloalkoxy-(Ci-C6)-haloalkyl, Hydrothio, R 7 , R 8 , R 9 and R 10 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, nitro, amino, cyano, (d-CeJ-alkyl, optionally substituted phenyl, heteroaryl, (C 3 -C 6 ) . cycloalkyl (C 4 -C 6) -cycloalkenyl, (C 2 -C 6) alkenyl, (C 2 -C 6) - alkynyl, (C2-C6) alkenyl (Ci-C 6) alkyl , (C 2 -C 6) alkynyl (Ci-C 6) alkyl, hydroxy, (Ci-C 6) alkoxy, (Ci-C6) alkoxy (Ci-C 6) alkoxy, ( Ci-C 6) alkoxy (Ci-C 6) alkyl, hydroxy (Ci-C 6) alkyl, (Ci-Ce) haloalkoxy, (Ci-C 6) -haloalkyl, (C 2 -C 6) - haloalkenyl, (C 2 -C 6) haloalkynyl, (Ci-C 6) haloalkoxy (Ci-C6) alkyl, (Ci-Ce) - alkoxy- (Ci-Ce) -haloalkyl, (C -C 6 ) -haloalkoxy- (C 1 -C 6 ) -haloalkyl, hydrothio,
(CrC6)-Alkylthio, (CrC6)-Haloalkylthio, (Ci-C6)-Alkylthio-(Ci-C6)-alkyl, (Ci-C6)- Haloalkylthio-(Ci-C6)-alkyl, (Ci-C6)-Alkylamino, Bis[(Ci-C6)-alkyl]amino, (C2-C6)- Alkenylamino, (C3-C6)-Cycloalkylamino, (d-CeJ-Alkylcarbonylamino, (Ca-Ce)- Cycloalkylcarbonylamino, Arylcarbonylamino, Heteroarylcarbonylamino, Formylamino, (Ci-CeJ-Haloalkylcarbonylamino, (CrC6)-Alkoxycarbonylamino, (Ci-C6)-Alkylaminocarbonylamino, (d-C6)-Alkyl[(Ci-C6)- Alkyljaminocarbonylamino, (Ci-CeJ-Alkylsulfonylamino, (Ca-Ce)- Cycloalkylsulfonylamino, Arylsulfonylamino, Hetarylsulfonylamino, Sulfonyl- (Ci-C6)-haloalkylamino, Amino-(Ci-C6)-alkylsulfonyl, Amino-(Ci-Ce)- haloalkylsulfonyl, (CrCeJ-Alkylaminosulfonyl, Bis[(d-C6)-alkyl]aminosulfonyl, (C3-C6)-Cycloalkylaminosulfonyl, (Ci-CeJ-Haloalkylaminosulfonyl, (CrC 6) alkylthio, (CrC 6) haloalkylthio, (Ci-C 6) alkylthio (Ci-C 6) alkyl, (Ci-C 6) - Haloalkylthio- (Ci-C 6) alkyl, (C 1 -C 6 ) -alkylamino, bis [(C 1 -C 6 ) -alkyl] -amino, (C 2 -C 6 ) -alkenylamino, (C 3 -C 6 ) -cycloalkylamino, (C 1 -C 6 -alkylcarbonylamino, (C 1 -C 6 ) -alkyl) Ce) - cycloalkylcarbonylamino, arylcarbonylamino, heteroarylcarbonylamino, formylamino, (Ci-CeJ-haloalkylcarbonylamino, (CrC6) -alkoxycarbonylamino, (Ci-C6) -alkylaminocarbonylamino, (d-C6) -alkyl [(Ci-C6) - alkyljaminocarbonylamino, (Ci -CeJ-alkylsulfonylamino, (Ca-Ce) -cycloalkylsulfonylamino, arylsulfonylamino, hetarylsulfonylamino, sulfonyl- (Ci-C6) -haloalkylamino, amino- (Ci-C6) -alkylsulfonyl, amino- (Ci-Ce) - haloalkylsulfonyl, (CrCeJ- Alkylaminosulfonyl, bis [(C 1 -C 6) -alkyl] aminosulfonyl, (C 3 -C 6) -cycloalkylaminosulfonyl, (C 1 -C 6 -haloalkylaminosulfonyl,
Heteroarylaminosulfonyl, Arylaminosulfonyl, Aryl-(CrC6)-alkylaminosulfonyl, (Ci-C6)-Alkylsulfonyl, (Ca-CeJ-Cycloalkylsulfonyl, Arylsuifonyl, Hydroxycarbonyl, (Ci-Cr,)-Alkoxycarbonyl, (Ca-CeJ-Cycloalkoxycarbonyl, (Ca-Ce Cycloalkyl-
(Ci-C-6)-alkoxycarbonyl, Aryloxycarbonyl, Aryl-(Ci-C-6)-alkoxycarbonyl, (Cz-Ce)- Alkenyloxycarbonyl, (C2-C6)-Alkinyloxycarbonyl, Aminocarbonyl, (d-Ce)- Alkylaminocarbonyl, Bis[(Ci-C6)-alkyl]aminocarbonyl, (Ci-C6)-Alkyl[(d-C6)- Alkyl]aminocarbonyl, (Ci-C6)-Alkyl[(CrC6)-Alkoxy]aminocarbonyl, (C2-Ce)- Alkenylaminocarbonyl, (C3-C6)-Cycloalkylaminocarbonyl, Arylaminocarbonyl, Aryl-(Ci-C6)-alkylaminocarbonyl stehen, Heteroarylaminosulfonyl, arylaminosulfonyl, aryl- (C 1 -C 6) -alkylaminosulfonyl, (C 1 -C 6) -alkylsulfonyl, (C 1 -C 12 -cycloalkylsulfonyl, arylsulfonyl, hydroxycarbonyl, (C 1 -C 8) -alkoxycarbonyl, (C 1 -C 12 -cycloalkoxycarbonyl, Ce cycloalkyl- (C 1 -C 6) -alkoxycarbonyl, aryloxycarbonyl, aryl- (C 1 -C 6) -alkoxycarbonyl, (Cz-Ce) -alkenyloxycarbonyl, (C 2 -C 6) -alkynyloxycarbonyl, aminocarbonyl, (d-Ce) -alkylaminocarbonyl, Bis [(Ci-C6) alkyl] aminocarbonyl, (Ci-C6) -alkyl [(d-C6) alkyl] aminocarbonyl, (Ci-C6) alkyl [(CrC6) alkoxy] aminocarbonyl, (C2-Ce ) - alkenylaminocarbonyl, (C 3 -C 6) -cycloalkylaminocarbonyl, arylaminocarbonyl, aryl- (C 1 -C 6) -alkylaminocarbonyl,
A1 , A2, A3 und A4 gleich oder verschieden sind und unabhängig voneinander für N A 1 , A 2 , A 3 and A 4 are the same or different and are independently N
(Stickstoff) oder die Gruppierungen C-H, C-CH3, C-F, C-Cl, C-Br, C-l, C-OCF3, C-OCH3, C-CF3, C-CO2H, C-CO2CH3 stehen, wobei jedoch in keinem Fall mehr als zwei N-Atome benachbart sind, (Nitrogen) or the groupings CH, C-CH 3, CF, C-Cl, C-Br, CI, C-OCF3, C-OCH3, C-CF3, C-CO2H, C-CO2CH3 are, however, in no more than two N-atoms are adjacent,
R11 und R12 unabhängig voneinander für Wasserstoff, Fluor, Chlor, Brom, lod, (d-Ce)- Alkyl, gegebenenfalls substituiertes Phenyl, Heteroaryl, Heterocyclyl, (Cs-Ce)- Cycloalkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, Aryloxy-(CrC6)-alkyl, (CrC6)-Haloalkyl, (Ci-C6)-Haloalkoxy-(Ci-C6)-alkyl, R 11 and R 12 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, (d-Ce) -alkyl, optionally substituted phenyl, heteroaryl, heterocyclyl, (Cs-Ce) -cycloalkyl, (C 2 -C 6 ) - alkenyl, (C 2 -C 6) -alkynyl, (Ci-C6) alkoxy (Ci-C 6) alkyl, aryloxy (CrC 6) alkyl, (CrC 6) -haloalkyl, (Ci-C6 Haloalkoxy- (C 1 -C 6 ) -alkyl,
(Ci-C6)-Alkoxy-(Ci-C6)-haloalkyl, (Ci-C6)-Haloalkoxy-(Ci-C6)-haloalkyl, (d-C6)- Alkylthio-(Ci-Cr>)-alkyl, Hydroxycarbonyl, (Ci-C6)-Alkoxycarbonyl, (C3-G3)- Cycloalkoxycarbonyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkoxycarbonyl, (Ci-C6) alkoxy (Ci-C6) -haloalkyl, (C 6) haloalkoxy (C 6) -haloalkyl, (dC 6) - alkylthio (Ci-Cr>) - alkyl, hydroxycarbonyl, (C 1 -C 6) -alkoxycarbonyl, (C 3 -G 3) -cycloalkoxycarbonyl, (C 3 -C 6) -cycloalkyl- (C 1 -C 6) -alkoxycarbonyl,
Aryloxycarbonyl, Aryl-(Ci-C6)-alkoxycarbonyl, (C2-C6)-Alkenyloxycarbonyl, Aryloxycarbonyl, aryl- (C 1 -C 6) -alkoxycarbonyl, (C 2 -C 6) -alkenyloxycarbonyl,
(C2-C6)-Alkinyloxycarbonyl, Aminocarbonyl, (CrC6)-Alkylaminocarbonyl, Bis[(Ci-C6)-alkyl]aminocarbonyl, (Ci-C6)-Alkyl[(d-C6)-Alkyl]aminocarbonyl, (Ci-C6)-Alkyl[(CrC6)-Alkoxy]aminocarbonyl, (C2-C6)-Alkenylaminocarbonyl, (C3-Cr,)-Cycloalkylaminocarbonyl, Arylaminocarbonyl, Aryl-(Ci-Ce)- alkylaminocarbonyl stehen, (C 2 -C 6) -alkynyloxycarbonyl, aminocarbonyl, (C 1 -C 6) -alkylaminocarbonyl, bis [(C 1 -C 6) -alkyl] aminocarbonyl, (C 1 -C 6) -alkyl [(C 1 -C 6) -alkyl] aminocarbonyl, C 6) -alkyl [(C 1 -C 6) -alkoxy] -aminocarbonyl, (C 2 -C 6) -alkenylaminocarbonyl, (C 3 -C 8) -cycloalkylaminocarbonyl, arylaminocarbonyl, aryl- (C 1 -C 6) -alkylaminocarbonyl,
A5 für S (Schwefel), O (Sauerstoff) oder die Gruppierungen N-H, N-CH3, N-CH2CH3, N- CH(CH3)2, N-C02t-Bu, N-Aryl, N-Heteroaryl, N-Heterocyclyl steht, A 5 for S (sulfur), O (oxygen) or the groupings NH, N-CH 3 , N-CH 2 CH 3 , N-CH (CH 3 ) 2 , N-CO 2 t-Bu, N-aryl, N-heteroaryl , N-heterocyclyl,
R13, R14, R17 und R18 unabhängig voneinander für Wasserstoff, (Ci-Ce)-Alkyl, Fluor, Chlor, Brom, lod, (Cs-CeJ-Cycloalkyl, gegebenenfalls substituiertes Phenyl, Heteroaryl, Heterocyclyl, (C2-Cc,)-Alkenyl, Aryl-(Ci-Ce)-alkyl, (Ci-Ce)-Alkoxy, (Ci-C6)-Alkoxy-(Ci-C6)-alkoxy, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl. Hydroxy, (d-Cr,)- Haloalkyl, (Ci-CeJ-Haloalkylthio stehen oder
R13 und R17 mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls weiter substituierten 5 bis 7-gliedrigen Ring bilden, R 13 , R 14 , R 17 and R 18 independently of one another represent hydrogen, (C 1 -C 6) -alkyl, fluorine, chlorine, bromine, iodine, (C 5 -C 12 -cycloalkyl, optionally substituted phenyl, heteroaryl, heterocyclyl, (C 2 -C 10) Cc,) - alkenyl, aryl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkoxy - (Ci-C 6 ) -alkyl, hydroxy, (d-Cr,) - haloalkyl, (Ci-CeJ-haloalkylthio or R 13 and R 17 with the atoms to which they are attached form a completely saturated or partially saturated, optionally further substituted 5 to 7-membered ring,
A6, A7 gleich oder verschieden sind und unabhängig voneinander für O (Sauerstoff), S (Schwefel), N-H, N-OCH3, N-CH3 oder die Gruppierung CR15R16 stehen, wobei jedoch in keinem Fall zwei N-, O- oder S-Atome benachbart sind, und wobei R15 und R16 in der Gruppierung CR15R16 jeweils gleiche oder verschiedene A 6 , A 7 are the same or different and are each independently O (oxygen), S (sulfur), NH, N-OCH 3 , N-CH 3 or the group CR 15 R 16 , but in no case two N -, O or S atoms are adjacent, and wherein R 15 and R 16 in the group CR 15 R 16 are identical or different
Bedeutungen gemäß der nachstehenden Definition haben und Have meanings as defined below and
R 5 und R16 unabhängig voneinander für Wasserstoff, Fluor, Chlor, Brom, lod, (d-Ce)- Alkyl, gegebenenfalls substituiertes Phenyl, Heteroaryl, Heterocyclyl, (Ca-Ce)- Cycloalkyl, (C2-C6)-Alkenyl, (Ci-C6)-Alkoxy, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, R 5 and R 16 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, (d-Ce) -alkyl, optionally substituted phenyl, heteroaryl, heterocyclyl, (Ca-Ce) -cycloalkyl, (C 2 -C 6 ) - Alkenyl, (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl,
(CrC6)-Haloalkoxy, (CrC6)-Haloalkyl, (Ci-C6)-Alkylthio, (Ci-C6)-Haloalkylthio, (Ci-C6)-Alkylthio-(Ci-C6)-alkyl, Hydroxycarbonyl, (d-C6)-Alkoxycarbonyl, (CrC 6) -haloalkoxy, (CrC 6) -haloalkyl, (Ci-C 6) alkylthio, (Ci-C 6) haloalkylthio, (Ci-C6) alkylthio (Ci-C6) alkyl, hydroxycarbonyl, (d-C6) alkoxycarbonyl,
(C3-C6)-Cycloalkoxycarbonyl, Aryl-(d-C6)-alkoxycarbonyl, (C2-C-6)- Alkenyloxycarbonyl, Aminocarbonyl, (Ci-C6)-Alkylaminocarbonyl, Bis[(Ci-Ce)- alkyljaminocarbonyl, (Ci-C6)-Alkyl[(Ci-C6)-Alkyl]aminocarbonyl, (C2-C6)- Alkenylaminocarbonyl, (C3-C6)-Cycloalkylaminocarbonyl, Aryl-(Ci-Ce)- alkylaminocarbonyl, Amino, (d-CeJ-Alkylamino, (Ca-Cc -Cycloalkylamino, Bis- [(Ci-C6)-Alkyl]amino stehen, (C 3 -C 6) -cycloalkoxycarbonyl, aryl- (C 1 -C 6) -alkoxycarbonyl, (C 2 -C 6) -alkenyloxycarbonyl, aminocarbonyl, (C 1 -C 6) -alkylaminocarbonyl, bis [(Ci-Ce) -alkyl-aminocarbonyl, (Ci -C 6) -alkyl [(C 1 -C 6) -alkyl] aminocarbonyl, (C 2 -C 6) -alkenylaminocarbonyl, (C 3 -C 6) -cycloalkylaminocarbonyl, aryl- (C 1 -C 6) -alkylaminocarbonyl, amino, (C 1 -C 6 -alkylamino , (C 1 -C 6 -cycloalkylamino, bis- [(C 1 -C 6) -alkyl] -amino,
R19, R20, R22 und R23 unabhängig voneinander für Wasserstoff, (Ci-C6)-Alkyl, Fluor, Chlor, Brom, lod, (C3-C6)-Cycloalkyl, Aryl, Heteroaryl, Heterocyclyl, (C2-C6)- Alkenyl, Aryl-(Ci-C6)-alkyl, (Ci-Cc)-Alkoxy, (Ci-C6)-Haloalkyl stehen, R 19 , R 20 , R 22 and R 23 independently of one another represent hydrogen, (C 1 -C 6) -alkyl, fluorine, chlorine, bromine, iodine, (C 3 -C 6) -cycloalkyl, aryl, heteroaryl, heterocyclyl, (C 2 -C 6) ) Alkenyl, aryl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -haloalkyl,
A8 für O (Sauerstoff), S (Schwefel), N-H, N-CH3, N-OCH3 oder die Gruppierung CHR21 steht und wobei R21 in der Gruppierung CHR21 die Bedeutung gemäß der nachstehenden Definition hat, A 8 is O (oxygen), S (sulfur), NH, N-CH 3, N -OCH 3 or the moiety CHR 21 , and wherein R 21 in the moiety CHR 21 has the meaning as defined below,
R21 für Wasserstoff, Fluor, Chlor, Brom, lod, (Ci-Ce)-Alkyl, gegebenenfalls R 21 is hydrogen, fluorine, chlorine, bromine, iodine, (C 1 -C 6) -alkyl, if appropriate
substituiertes Phenyl, Heteroaryl, Heterocyclyl, (C3-Cr>)-Cycloalkyl, (C2-C6)- Alkenyl, (Ci-C6)-Alkoxy, (CrC6)-Haloalkoxy, (CrC6)-Haloalkyl, (CrC6)-Alkylthio,
(Ci-C-6)-Haloalkylthio, Hydroxycarbonyl, Aryl-(Ci-C-6)-alkoxycarbonyl, (Cz-Ce)- Alkenyloxycarbonyl, Aminocarbonyl, (Ci-Cc>)-Alkylaminocarbonyl, Bis[(Ci-Ce)- alkyl]aminocarbonyl, (Ci-C6)-Alkyl[(CrC6)-Alkyl]aminocarbonyl, (Ci-Ce)- Alkyl[(CrC6)-Alkoxy]aminocarbonyl, (C2-C6)-Alkenylaminocarbonyl, (Cs-Co)- Cycloalkylaminocarbonyl, Aryl-(Ci-C6)-alkylaminocarbonyl, Amino, (Ci-Ce)- Alkylamino, (Ca-CeJ-Cycloalkylamino, Bis[(Ci-Cr,)-Alkyl]amino sieht, substituted phenyl, heteroaryl, heterocyclyl, (C3-Cr>) cycloalkyl, (C2-C6) - alkenyl, (Ci-C 6) alkoxy, (CrC 6) -haloalkoxy, (CrC 6) -haloalkyl, (CrC 6 ) alkylthio, (Ci-C-6) -haloalkylthio, hydroxycarbonyl, aryl- (Ci-C-6) -alkoxycarbonyl, (Cz-Ce) -alkenyloxycarbonyl, aminocarbonyl, (Ci-Cc > ) -alkylaminocarbonyl, bis [(Ci-Ce) alkyl] aminocarbonyl, (C 1 -C 6) -alkyl [(C 1 -C 6) -alkyl] aminocarbonyl, (C 1 -C 6) -alkyl [(C 1 -C 6) -alkoxy] aminocarbonyl, (C 2 -C 6) -alkenylaminocarbonyl, (Cs-Co) - cycloalkylaminocarbonyl, aryl- (Ci-C6) -alkylaminocarbonyl, amino, (Ci-Ce) - alkylamino, (Ca-CeJ-cycloalkylamino, bis [(Ci-Cr,) - alkyl] amino,
R24, R25, R26, R28, R29 und R30 unabhängig voneinander für Wasserstoff, (Ci-C6)-Alkyl, Fluor, Chlor, Brom, lod, (Ca-Ce^-Cycloalkyl, Aryl, Heteroaryl, Heterocyclyl, (C2-C6)-Alkenyl, (Ci-Ce)-Alkoxy, (Ci-C6)-Haloalkyl, (Ci-Ce)-Alkylthio, (Ci-C6)- Haloalkylthio stehen, R 24 , R 25 , R 26 , R 28 , R 29 and R 30 independently of one another are hydrogen, (C 1 -C 6 ) -alkyl, fluorine, chlorine, bromine, iodine, (C 1 -C 4 -cycloalkyl, aryl, heteroaryl , Heterocyclyl, (C 2 -C 6 ) -alkenyl, (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -haloalkyl, (C 1 -C 6 ) -alkylthio, (C 1 -C 6 ) -haloalkylthio,
A9 für O (Sauerstoff), S (Schwefel), N-H, N-CH3, N-OCH3 oder die Gruppierung CHR27 steht und wobei R27 in der Gruppierung CHR27 die Bedeutung gemäß der nachstehenden Definition hat und A 9 is O (oxygen), S (sulfur), NH, N-CH 3 , N-OCH 3 or the moiety CHR 27 and wherein R 27 in the moiety CHR 27 has the meaning as defined below and
R27 für Wasserstoff, Fluor, Chlor, Brom, lod, (Ci-Ce)-Alkyl, gegebenenfalls R 27 is hydrogen, fluorine, chlorine, bromine, iodine, (C 1 -C 6) -alkyl, if appropriate
substituiertes Phenyl, Heteroaryl, Heterocyclyl, (C3-C6)-Cycloalkyl, (C2-C6)- Alkenyl, (Ci-C6)-Alkoxy, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Haloalkoxy, substituted phenyl, heteroaryl, heterocyclyl, (C 3 -C 6 ) -cycloalkyl, (C 2 -C 6 ) -alkenyl, (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkoxy,
(Ci-Cö)-Haloalkyl, (Ci-Cö)-Alkylthio, (Ci-C6)-Haloalkylthio, Hydroxycarbonyl, (d-C6)-Alkoxycarbonyl, (C3-C6)-Cycloalkoxycarbonyl, Aryl-(Ci-Ce)- alkoxycarbonyl, Aminocarbonyl, (Ci-C6)-Alkylaminocarbonyl, Bis[(Ci-Ce)- alkyl]aminocarbonyl, (C3-C6)-Cycloalkylaminocarbonyl, Aryl-(Ci-Ce)- alkylaminocarbonyl, Amino, (d-CeJ-Alkylamino, (Ca-Ce^Cycloalkylamino, Bis[(Ci-C6)-Alkyl]amino steht. (C 1 -C 6 ) -haloalkyl, (C 1 -C 6 ) -alkylthio, (C 1 -C 6 ) -haloalkylthio, hydroxycarbonyl, (C 1 -C 6 ) -alkoxycarbonyl, (C 3 -C 6 ) -cycloalkoxycarbonyl, aryl- (C 1 -C 4) alkoxycarbonyl, aminocarbonyl, (C 1 -C 6) -alkylaminocarbonyl, bis [(C 1 -C 6) -alkyl] aminocarbonyl, (C 3 -C 6) -cycloalkylaminocarbonyl, aryl- (C 1 -C 6) -alkylaminocarbonyl, amino, (d-Ce) -cycloalkylaminocarbonyl, Alkylamino, (Ca-Ce ^ cycloalkylamino, bis [(Ci-C 6 ) alkyl] amino.
Besonders bevorzugt sind Verbindungen der allgemeinen Formel (I), die durch die Formeln (la) bis (lo) beschrieben werden, Particular preference is given to compounds of the general formula (I) which are described by the formulas (Ia) to (Io)
worin wherein
[X-Y] für die Gruppierung [X-Y] for grouping
[X-Yl1 steht, für die Gruppierungen Q-1 bis Q-6
[X-Yl 1 stands for the groupings Q-1 to Q-6
steht, wobei R7, R8, R9, R10, R11 , R12, R13, R 4, R17, R18, R19, R20, R22, R23, R24, R25, R26, R28, R29 und R30 und A1 bis A9 jeweils die Bedeutung gemäß der nachstehenden Definitionen haben und wobei der Pfeil für eine Bindung zur jeweiligen Gruppierung C-R6 in den vorgenannten Formeln (la) bis (lo) steht, where R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 4 , R 17 , R 18 , R 19 , R 20 , R 22 , R 23 , R 24 , R 25 , R 26 , R 28 , R 29 and R 30 and A 1 to A 9 each have the meaning according to the definitions below and wherein the arrow for a bond to the respective group CR 6 in the aforementioned formulas (la) to (lo) .
R5 für Hydroxy, (Ci-Cf,)-Alkoxy, Aryloxy, (C3-C6)-Cycloalkyloxy, (C2-Ce)-Alkenyloxy, (C2-C6)-Alkenyl-(Ci-C6)-alkyloxy, (Ci-C6)-Alkoxy-(Ci-C6)-alkyloxy, (Ci-C6)- Alkylcarbonyloxy, Arylcarbonyloxy, Heteroarylcarbonyloxy, (C3-C6)- Cycloalkylcarbonyloxy, (Ci-Cr-Alkoxycarbonyloxy, (C2-Cr,)- Alkenyloxycarbonyloxy, Aryloxy-(Ci-Cr,)-alkyloxy, Aryl-(CrCö)-alkyloxy, (d-Ce)- Alkoxy-(Ci-C6)-alkoxy-(Ci-C6)-alkyloxy, (Ci-C6)-Alkylthio-(Ci-Ce)-alkyloxy, Tris[(Ci-C6)-alkyl]silyloxy, (Ci-C6)-Alkyl-Bis[(Ci-C6)-alkyl]silyloxy, (Ci-C6)-Alkyl- bis(Aryl)silyloxy, Aryl-bis[(d-C6)-alkyl]silyloxy, Cycloalkyl-bis[(Ci-C-6)- alkyljsilyloxy, Halo-bis[(Ci-C6)-alkyl]silyloxy, Tris[(Ci-C6)-alkyl]silyl-(Ci-C6)- alkoxy-(Ci-Cr>)-alkyloxy, steht, R 5 is hydroxy, (C 1 -C 5) -alkoxy, aryloxy, (C 3 -C 6 ) -cycloalkyloxy, (C 2 -C 6 ) -alkenyloxy, (C 2 -C 6 ) -alkenyl- (C 1 -C 6 ) -alkyloxy, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyloxy, (C 1 -C 6 ) -alkylcarbonyloxy, arylcarbonyloxy, heteroarylcarbonyloxy, (C 3 -C 6 ) -cycloalkylcarbonyloxy, (C 1 -C 6 -alkoxycarbonyloxy, (C 2 -C 4 ) -cyclocarbonyloxy Alkenyloxycarbonyloxy, aryloxy- (Ci-Cr,) -alkyloxy, aryl- (C 1 -C 6) -alkyloxy, (d-Ce) -alkoxy- (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyloxy, (C 1 -C 6 ) -alkylthio (C 1 -C 6 ) -alkyloxy, tris [(C 1 -C 6 ) -alkyl] silyloxy, (C 1 -C 6 ) -alkyl-bis [(C 1 -C 6 ) -alkyl] silyloxy, (C 1 -C 6 ) alkyl bis (aryl) silyloxy, aryl bis [(C 1 -C 6 ) alkyl] silyloxy, cycloalkyl bis [(C 1 -C 6) alkyl] silyloxy, halo bis [( Ci-C6) alkyl] silyloxy, tris [(C 6) alkyl] silyl (Ci-C6) - alkoxy (Ci-Cr>) alkyloxy, stands,
R6 für (C1-C5)- Alkylsulfonylaminocarbonyl, (C3-G5)-R 6 is (C 1 -C 5 ) -alkylsulfonylaminocarbonyl, (C 3 -G 5) -
Cycloalkylsulfonylaminocarbonyl, Hydroxycarbonyl, (Ci-C6)-Alkoxycarbonyl, (Ca-CeJ-Cycloalkoxycarbonyl, (C3-C6)-Cycloalkyl-(CrC5)-alkoxycarbonyl, Aryloxycarbonyl, Aryl-(CrC5)-alkoxycarbonyl, (C2-C6)-Alkenyloxycarbonyl, (C2-C6)-Alkinyloxycarbonyl, (CrCsJ-Haloalkyloxycarbonyl, (Ci-Cs)-Alkoxy- (Ci-C5)-alkoxycarbonyl, (C2-Cö)-Alkenyloxy-(Ci-C5)-alkoxycarbonyl, (C1-C5)- Alkylamino-(Ci-Cf))-alkoxycarbonyl, Tris[(Ci-C6)-alkyl]silyloxy-(Ci-C6)-
alkoxycarbonyl, Bis[(Ci-C6)-Alkyl]amino-(Ci-C6)-alkoxycarbonyl, (Ci-Ce)- Alkyl[(CrC6)-alkyl]amino-(Ci-Cö)-alkoxycarbonyl, Cyano-(d-C6)- alkoxycarbonyl, Heterocyclyl-N-(Ci-C5)-alkoxycarbonyl, Heteroaryloxycarbonyl, Heteroaryl-(CrCr>)-alkoxycarbonyl, Heterocyclyl-(Ci-Cr>)-alkoxycarbonyl, Heterocyclyloxycarbonyl, (C2-Cr,)-Alkenyl-(Ci-C5)-alkoxycarbonyl, (C2-Ce)- Alkinyl-(Ci-C5)-alkoxycarbonyl, Aryl-(C2-C6)-alkinyloxycarbonyl, Aryl-(C2-Ce)- alkenyloxycarbonyl, Aminocarbonyl, (CrCeJ-Alkylaminocarbonyl, Bis[(d-C6)- alkyl]aminocarbonyl, (Ci-C6)-Alkyl[(Ci-C6)-Alkyl]aminocarbonyl, (d-Ce)- Alkyl[(Ci-C6)-Alkoxy]aminocarbonyl, (C2-C6)-Alkenylaminocarbonyl, (Ca-Ce)- Cycioalkylaminocarbonyl, Arylaminocarbonyl, Aryl-(Ci-C5)-alkylaminocarbonyl, Heteroaryl-(Ci-Cr>)-alkylaminocarbonyl, Cyano-(Ci-C5)-alkylaminocarbonyl, (Ci-C5)-Haloalkylaminocarbonyl, (C2-C6)-Alkinyl-(CrC5)-alkylaminocarbonyl, (Ci-C5)-Alkoxycarbonylaminocarbonyl, Aryl-(Ci-Cs)- alkoxycarbonylaminocarbonyl, Hydroxycarbonyl-(Ci-C5)-alkyl, (C1-C5)- Alkoxycarbonyl-(Ci-C5)-alkyl, (C3-C6)-Cycloalkoxycarbonyl-(Ci-C5)-alkyl, (C3-C6)-Cycloalkyl-(Ci-C5)-alkoxycarbonyl-(Ci-C5)-alkyl, (C2-C6)- Alkenyloxycarbonyl-(Ci-C5)-alkyl, Aryl-(Ci-C5)-alkoxycarbonyl-(CrC5)-alkyl, (Ci-C5)-Alkylaminocarbonyl-(Ci-C5)-alkyl, Aminocarbonyl-(Ci-C5)-alkyl, Cycloalkylsulfonylaminocarbonyl, hydroxycarbonyl, (C 1 -C 6) -alkoxycarbonyl, (C 1 -C 12 -cycloalkoxycarbonyl, (C 3 -C 6) -cycloalkyl- (C 1 -C 5) -alkoxycarbonyl, aryloxycarbonyl, aryl- (C 1 -C 5) -alkoxycarbonyl, (C 2 -C 6) -alkenyloxycarbonyl , (C 2 -C 6) -alkynyloxycarbonyl, (C 1 -C 6 -haloalkyloxycarbonyl, (C 1 -C 8) -alkoxy- (C 1 -C 5) -alkoxycarbonyl, (C 2 -C 6) -alkenyloxy- (C 1 -C 5) -alkoxycarbonyl, (C 1 -C 5) ) - alkylamino- (Ci-Cf)) - alkoxycarbonyl, tris [(Ci-C6) -alkyl] silyloxy- (Ci-C6) - alkoxycarbonyl, bis [(C 1 -C 6) alkyl] amino- (C 1 -C 6) alkoxycarbonyl, (C 1 -C 6) alkyl [(C 1 -C 6) alkyl] amino (C 1 -C 6) alkoxycarbonyl, cyano (i.e. C6) - alkoxycarbonyl, heterocyclyl-N- (Ci-C5) alkoxycarbonyl, heteroaryloxycarbonyl, heteroaryl (CrCr>) -alkoxycarbonyl, heterocyclyl (Ci-Cr>) alkoxycarbonyl, heterocyclyloxycarbonyl, (C2-Cr,) - alkenyl - (C 1 -C 5) -alkoxycarbonyl, (C 2 -C 6) -alkynyl- (C 1 -C 5) -alkoxycarbonyl, aryl- (C 2 -C 6) -alkynyloxycarbonyl, aryl- (C 2 -C 6) -alkenyloxycarbonyl, aminocarbonyl, (CrCeJ-) Alkylaminocarbonyl, bis [(C 1 -C 6) -alkyl] aminocarbonyl, (C 1 -C 6) -alkyl [(C 1 -C 6) -alkyl] aminocarbonyl, (C 1 -C 6) -alkyl [(C 1 -C 6) -alkoxy] -aminocarbonyl, (C2-C6) -Alkenylaminocarbonyl, (Ca-Ce) - Cycioalkylaminocarbonyl, arylaminocarbonyl, aryl (C-C5) alkylaminocarbonyl, heteroaryl (Ci-Cr>) alkylaminocarbonyl, cyano (C-C5) alkylaminocarbonyl ( C 1 -C 5) -haloalkylaminocarbonyl, (C 2 -C 6) -alkynyl- (C 1 -C 5) -alkylaminocarbonyl, (C 1 -C 5) -alkoxycarbonylaminocarbonyl, aryl- (C 1 -C 8) -alkoxycarbonylaminocarbonyl, hydroxycarbonyl- (C 1 -C 5) -a alkyl, (C 1 -C 5) -alkoxycarbonyl- (C 1 -C 5 ) -alkyl, (C 3 -C 6) -cycloalkoxycarbonyl- (C 1 -C 5 ) -alkyl, (C 3 -C 6) -cycloalkyl- (C 1 -C 5 ) - alkoxycarbonyl- (C 1 -C 5 ) -alkyl, (C 2 -C 6 ) -alkenyloxycarbonyl- (C 1 -C 5 ) -alkyl, aryl- (C 1 -C 5 ) -alkoxycarbonyl- (C 1 -C 5 ) -alkyl, (C 1 -C 5 ) -Alkylaminocarbonyl- (C 1 -C 5) -alkyl, aminocarbonyl- (C 1 -C 5) -alkyl,
Bis[(Ci-C6)-alkyl]aminocarbonyl-(Ci-C5)-alkyl, (Ca-CeJ-Cycloalkylaminocarbonyl- (Ci-C5)-alkyl, Aryl-(Ci-C6)-alkylaminocarbonyl-(Ci-C5)-alkyl, Heteroaryl-(Ci-C5)- alkylaminocarbonyl-(Ci-C5)-alkyl, Cyano-(Ci-C5)-alkylaminocarbonyl-(Ci-C5)- alkyl, (Ci-C5)-Ha!oalkylaminocarbonyl-(Ci-C5)-alkyl, (C2-C6)-Alkinyl-(Ci-C5)- alkylaminocarbonyl-(Ci-C5)-alkyl, (C3-C6)-Cycloalkyl-(Ci-C5)- alkylaminocarbonyl-(Ci-Cr>)-alkyl, (Ci-Cr>)-Alkoxycarbony!aminocarbonyl- (Ci-C5)-alkyl, Aryl-(Ci-C5)-alkoxycarbonylaminocarbonyl-(Ci-Cr>)-alkyl, (Ci-Ce)- Alkoxycarbonyl-(Ci-C6)-alkylaminocarbonyl, Hydroxycarbonyl-(Ci-C6)- alkylaminocarbonyl, Aryi-(Ci-C6)-alkoxycarbonyl-(Ci-C6)-alkylaminocarbonyl, Aminocarbonyl-(Ci-C6)-alkylaminocarbonyl, (Ci-C6)-Aikylaminocarbonyl- (Ci-C6)-alkylaminocarbonyi, Aminosulfonyl, (Ci-Cr,)-Alkoxycarbonyl- heterocyclyl-N-carbonyl, (CrC6)-Alkoxycarbonyl-(Ci-C6)-alkyl- heterocyclylidenaminocarbonyl, (Ci-C6)-Alkoxycarbonylheterocyclyliden-(Ci-Cr>)- alkylaminocarbonyl (Ci-C6)-Alkoxycarbonyl-(CrC6)-Alkyl((Ci-C6)- alkyl)aminocarbonyl, (Ci-C6)-Alkoxycarbonyl-(C3-C6)- cycloalkylidenaminocarbonyl, Heterocyclyl-N-carbonyl, (d-C6)-Alkoxy-(Ci-C6)-
alkylaminocarbonyl,(C3-C6)-Cycloalkylaminocarbonyl-(Ci-C6)- alkylaminocarbonyl, (C3-C6)-Cycloalkyl-(Ci-Cc,)-alkylaminocarbonyl, (Cj-Ce)- Cycloalkyl-(Ci-C6)-alkylaminocarbonyl-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl-(Ci-C6)- alkylaminocarbonyl-(Ci-C6)-alkylaminocarbonyl, (C2-C6)-Alkenyl-(d-C6)- alkylaminocarbonyl, (C2-C6)-Alkenylaminocarbonyl-(Ci-Cö)-alkyl, (C2-Ce)- Alkenyl-(Ci-C6)-alkylaminocarbonyl-(Ci-C6)-alkyl, (Ci-C6)-Alkylcarbonyl, (C3-C6)- Cycloalkylcarbonyl, Arylcarbonyl, Formyl, Hydroxyiminomethyl, Bis [(Ci-C6) -alkyl] aminocarbonyl- (Ci-C5) -alkyl, (Ca-CeJ-Cycloalkylaminocarbonyl- (Ci-C 5 ) -alkyl, aryl- (Ci-C6) -alkylaminocarbonyl- (Ci-C 5 ) -alkyl, heteroaryl- (C 1 -C 5 ) -alkylaminocarbonyl- (C 1 -C 5 ) -alkyl, cyano- (C 1 -C 5 ) -alkylaminocarbonyl- (C 1 -C 5 ) -alkyl, (C 1 -C 5 ) -Ha ! oalkylaminocarbonyl- (C 1 -C 5 ) -alkyl, (C 2 -C 6 ) -alkynyl- (C 1 -C 5 ) -alkylaminocarbonyl- (C 1 -C 5 ) -alkyl, (C 3 -C 6 ) -cycloalkyl- (Ci -C 5 ) - alkylaminocarbonyl- (Ci-Cr > ) alkyl, (Ci-Cr > ) -Alkoxycarbony! Aminocarbonyl- (Ci-C5) -alkyl, aryl- (Ci-C5) -alkoxycarbonylaminocarbonyl- (Ci-Cr > ) -alkyl, (C 1 -C 6) -alkoxycarbonyl- (C 1 -C 6) -alkylaminocarbonyl, hydroxycarbonyl- (C 1 -C 6) -alkylaminocarbonyl, aryl- (C 1 -C 6) -alkoxycarbonyl- (C 1 -C 6) -alkylaminocarbonyl, aminocarbonyl- (C 1 -C 6) -alkylaminocarbonyl, (C 1 -C 6) -alkylaminocarbonyl- (C 1 -C 6) -alkylaminocarbonyi, aminosulfonyl, (C 1 -C 8) -alkoxycarbonyl-heterocyclyl-N-carbonyl, (C 1 -C 6) -alkoxycarbonyl- (C 1 -C 4) -cyclo C6) alkyl heterocyclylidenaminocarbonyl, (Ci-C6) -Alkoxycarbonylheterocyclyliden- (Ci-Cr>) - alkylaminocarbon yl (C 1 -C 6) -alkoxycarbonyl- (C 1 -C 6) -alkyl ((C 1 -C 6) -alkyl) aminocarbonyl, (C 1 -C 6) -alkoxycarbonyl- (C 3 -C 6) -cycloalkylideneaminocarbonyl, heterocyclyl-N-carbonyl, (n- C6) alkoxy (Ci-C6) - alkylaminocarbonyl, (C3-C6) -cycloalkylaminocarbonyl- (Ci-C6) -alkylaminocarbonyl, (C3-C6) -cycloalkyl- (Ci-Cc,) - alkylaminocarbonyl, (Cj-Ce) -cycloalkyl- (Ci-C6) -alkylaminocarbonyl (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkylaminocarbonyl- (C 1 -C 6 ) -alkylaminocarbonyl, (C 2 -C 6 ) -alkenyl- (C 1 -C 6 ) - alkylaminocarbonyl, (C 2 -C 6 ) -alkenylaminocarbonyl- (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl- (C 1 -C 6 ) -alkylaminocarbonyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) - Alkylcarbonyl, (C 3 -C 6 ) -cycloalkylcarbonyl, arylcarbonyl, formyl, hydroxyiminomethyl,
Aminoiminomethyl, (CrCr -Alkoxyiminomethyl, (Ci-C6)-Alkylaminoiminomethyl, Bis[(Ci-C6)-alkyl]aminoiminomethyl, (C3-C6)-Cycloalkoxyiminomethyl, (C3-Ce)- Cycloalkyl-(Ci-C6)-alkoximinomethyl, Aryloximinomethyl, Aryl-(Ci-Ce)- alkoxyiminomethyl, Aryl-(Ci-C6)-alkylaminoiminomethyl, (C2-Ce)- Alkenyloxyiminomethyl, Arylaminoiminomethyl, Arylsulfonylaminoiminomethyl, Hydroxyaminocarbonyl, (Ci-CeJ-Alkoxyaminocarbonyl, Aryl-(Ci-Ce)- alkoxyaminocarbonyl steht, Aminoiminomethyl, (CrCr-alkoxyiminomethyl, (C 1 -C 6) -alkylaminoiminomethyl, bis [(C 1 -C 6) -alkyl] aminoiminomethyl, (C 3 -C 6) -cycloalkoxyiminomethyl, (C 3 -C 6) -cycloalkyl- (C 1 -C 6) -alkoximinomethyl , Aryloximinomethyl, aryl- (Ci-Ce) -alkoxyiminomethyl, aryl- (Ci-C6) -alkylaminoiminomethyl, (C2-Ce) -alkenyloxyiminomethyl, arylaminoiminomethyl, arylsulfonylaminoiminomethyl, hydroxyaminocarbonyl, (Ci-CeJ-alkoxyaminocarbonyl, aryl- (Ci-Ce ) - alkoxyaminocarbonyl,
R7, R8 , R9 und R10 unabhängig voneinander für Wasserstoff, Fluor, Chlor, Brom, lod, Nitro, Amino, Cyano, (Ci-C-5)-Alkyl, gegebenenfalls substituiertes Phenyl, Heteroaryl, (C3-C6)-Cycloalkyl, (C4-C6)-Cycloalkenyl, (C2-C5)-Alkenyl, (C2-C5)- Alkinyl, (C2-C5)-Alkenyl-(Ci-C5)-alkyl, (C2-C5)-Alkinyl-(Ci-Cr»)-alkyl, Hydroxy, (Ci-C5)-Alkoxy, (Ci-C5)-Alkoxy-(Ci-C5)-alkoxy, (Ci-C5)-Alkoxy-(Ci-C5)-alkyl, Hydroxy-(Ci-C5)-alkyl, (CrC5)-Haloalkoxy, (Ci-C5)-Haloalkyl, (C2-C5)- Haloalkenyl, (C2-C5)-Haloalkinyl, (Ci-C5)-Haloalkoxy-(Ci-C5)-alkyl, (C1-C5)- Alkoxy-(CrC5)-haloalkyl, (Ci-C5)-Haloalkoxy-(Ci-C5)-haloalkyl, Hydrothio, (Ci-C5)-Alkylthio, (Ci-C5)-Haloalkylthio, (Ci-C5)-Alkylthio-(Ci-C5)-alkyl, (C1-C5)- Haloalkylthio-(Ci-C5)-alkyl, (Ci-C5)-Alkylamino, Bis[(Ci-C5)-alkyl]amino, (C2-C5)- Alkenylamino, (Cs-Ce Cycloalkylamino, (Ci-Cr>)-Alkylcarbonylamino, (Ca-Ce)- Cycloalkylcarbonylamino, Arylcarbonylamino, Heteroarylcarbonylamino, Formylamino, (Ci-C5)-Haloalkylcarbonylamino, (Ci-C5)-Alkoxycarbonylamino, (Ci-C5)-Alkylaminocarbonylamino, (Ci-C5)-Alkyl[(Ci-C5)- Alkyljaminocarbonylamino, (Ci-Cr>)-Alkylsulfonylamino, (C3-C6)- Cycloalkylsulfonylamino, Arylsulfonylamino, Hetarylsulfonylamino, Sulfonyl- (CrCr -haloalkylamino, Amino-(CrC5)-alkylsulfonyl, Amino-(CrCr>)- haloalkylsulfonyl, (Ci-CsJ-Alkylaminosulfonyl, Bis[(CrC5)-alkyl]aminosulfonyl, (C3-C6)-Cycloalkylaminosulfonyl, (Ci-CsJ-Haloalkylaminosulfonyl,
Heteroarylaminosulfonyl, Arylaminosulfonyl, Aryl-(Ci-C5)-alkylaminosulfonyl, (CrCr>)-Alkylsulfonyl, (C3-C6)-Cycloalkylsulfonyl, Arylsulfonyl, Hydroxycarbonyl, (Ci-C5)-Alkoxycarbonyl, (C3-Cc>)-Cycloalkoxycarbonyl, (Ca-CeJ-Cycloalkyl- (Ci-C5)-alkoxycarbonyl, Aryioxycarbonyl, Aryl-(d-C5)-alkoxycarbonyl, (C2-C5)- Alkenyloxycarbonyl, (C2-Cr,)-Alkinyloxycarbonyl, Aminocarbonyl, (C1-C5)- Alkylaminocarbonyl, Bis[(Ci-C5)-alkyl]aminocarbonyl, (Ci-Cr>)-Alkyl[(Ci-Cr>)- Alkyljaminocarbonyl, (Ci-C5)-Alkyl[(CrC5)-Alkoxy]aminocarbonyl, (C2-C5)- Alkenylaminocarbonyl, (Ca-CeJ-Cycloalkylaminocarbonyl, Arylaminocarbonyl, Aryl-(Ci-C5)-alkylaminocarbonyl stehen, R 7 , R 8 , R 9 and R 10 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, nitro, amino, cyano, (C 1 -C 5) -alkyl, optionally substituted phenyl, heteroaryl, (C 3 - C 6) cycloalkyl, (C 4 -C 6) -cycloalkenyl, (C 2 -C 5) alkenyl, (C2-C5) - alkynyl, (C2-C5) alkenyl (Ci-C 5) - alkyl, (C 2 -C 5 ) -alkynyl- (C 1 -C 6 -alkyl), hydroxy, (C 1 -C 5 ) -alkoxy, (C 1 -C 5 ) -alkoxy- (C 1 -C 5 ) -alkoxy, ( Ci-C 5) alkoxy (Ci-C 5) alkyl, hydroxy (Ci-C 5) alkyl, (CrC 5) haloalkoxy, (Ci-C5) haloalkyl, (C2-C5) - haloalkenyl, (C 2 -C 5) haloalkynyl, (Ci-C 5), haloalkoxy (Ci-C 5) alkyl, (C1-C5) - alkoxy (-C 5) haloalkyl, (Ci-C 5 ) -Haloalkoxy- (Ci-C 5 ) -haloalkyl, hydrothio, (Ci-C 5 ) -alkylthio, (Ci-C 5 ) haloalkylthio, (Ci-C 5 ) -alkylthio (Ci-C 5 ) -alkyl , (C 1 -C 5 ) -haloalkylthio (C 1 -C 5 ) -alkyl, (C 1 -C 5 ) -alkylamino, bis [(C 1 -C 5 ) -alkyl] -amino, (C 2 -C 5 ) -alkenylamino, (Cs -ce cycloalkylamino, (Ci-Cr>) alkylcarbonylamino, (Ca-Ce) - cycloalkylcarbonylamino, arylcarbonylamino, Heteroarylcarbonylamin o, formylamino, (C 1 -C 5) -haloalkylcarbonylamino, (C 1 -C 5) -alkoxycarbonylamino, (C 1 -C 5) -alkylaminocarbonylamino, (C 1 -C 5) -alkyl [(C 1 -C 5) -alkylaminocarbonylamino, (C 1 -C 8 -cr > ) Alkylsulfonylamino, (C3-C6) -cycloalkylsulfonylamino, arylsulfonylamino, hetarylsulfonylamino, sulfonyl- (CrCr-haloalkylamino, amino- (CrC5) -alkylsulfonyl, amino- (CrCr>) -haloalkylsulfonyl, (Ci-CsJ-alkylaminosulfonyl, bis [(CrC5 ) -alkyl] aminosulfonyl, (C 3 -C 6) -cycloalkylaminosulfonyl, (C 1 -C 8 -alkylalkylsulfonyl, Heteroarylaminosulfonyl, arylaminosulfonyl, aryl- (Ci-C5) alkylaminosulfonyl, (CrCr>) alkylsulfonyl, (C3-C6) cycloalkylsulfonyl, arylsulfonyl, hydroxycarbonyl, (Ci-C5) alkoxycarbonyl, (C3-Cc>) cycloalkoxycarbonyl, (Ca-CeJ-cycloalkyl- (Ci-C5) -alkoxycarbonyl, aryioxycarbonyl, aryl- (d-C5) -alkoxycarbonyl, (C2-C5) -alkenyloxycarbonyl, (C2-Cr,) - alkynyloxycarbonyl, aminocarbonyl, (C1-C5 ) - alkylaminocarbonyl, bis [(Ci-C5) alkyl] aminocarbonyl, (Ci-Cr>) alkyl [(Ci-Cr>) - Alkyljaminocarbonyl, (Ci-C5) alkyl, [(CRC5) alkoxy] aminocarbonyl, (C2-C5) - alkenylaminocarbonyl, (Ca-CeJ-cycloalkylaminocarbonyl, arylaminocarbonyl, aryl- (Ci-C5) -alkylaminocarbonyl,
A1 , A2, A3 und A4 gleich oder verschieden sind und unabhängig voneinander für N A 1 , A 2 , A 3 and A 4 are the same or different and are independently N
(Stickstoff) oder die Gruppierungen C-H, C-CH3, C-F, C-Cl, C-Br, C-l, C-OCF3, C-OCH3, C-CF3, C-CO2H, C-CO2CH3 stehen, wobei jedoch in keinem Fall mehr als zwei N-Atome benachbart sind, (Nitrogen) or the groupings CH, C-CH 3, CF, C-Cl, C-Br, CI, C-OCF3, C-OCH3, C-CF 3, C-CO2H, C-CO2CH3 are, however, in no more than two N-atoms are adjacent,
R11 und R12 unabhängig voneinander für Wasserstoff, Fluor, Chlor, Brom, lod, (C1-C5)- Alkyl, gegebenenfalls substituiertes Phenyl, Heteroaryl, Heterocyclyl, (Cs-Ce)- Cycloalkyl. (C2-C5)-Alkenyl, (C2-C5)-Alkinyl, (Ci-C5)-Haloalkyl, (C1-C5)- Haloalkoxy-(Ci-C5)-alkyl, (Ci-C5)-Alkylthio-(Ci-C5)-alkyl, Hydroxycarbonyl, R 11 and R 12 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, (C 1 -C 5) -alkyl, optionally substituted phenyl, heteroaryl, heterocyclyl, (Cs-Ce) -cycloalkyl. (C 2 -C 5) alkenyl, (C 2 -C 5) alkynyl, (Ci-C5) haloalkyl, (C1-C5) - haloalkoxy (Ci-C 5) alkyl, (Ci-C 5 ) -alkylthio (C 1 -C 5 ) -alkyl, hydroxycarbonyl,
(Ci-Cr>)-Alkoxycarbonyl, (C3-C6)-Cycloalkoxycarbonyl, (C3-C6)-Cycloalkyl- (d-CsJ-alkoxycarbonyl, Aryioxycarbonyl, Aryl-(CrCr>)-alkoxycarbonyl, (C2-C5)- Alkenyloxycarbonyl, (C2-C5)-Alkinyloxycarbonyl, Aminocarbonyl, (C1-C5)- Alkylaminocarbonyl, Bis[(Ci-C5)-alkyl]aminocarbonyl, (Ci-Cr,)-Alkyl[(Ci-C5)- Alkyl]aminocarbonyl, (Ci-Cr>)-Alkyl[(Ci-C5)-Alkoxy]aminocarbonyl, (C2-C5)- Alkenylaminocarbonyl, (Cs-CeJ-Cycloalkylaminocarbonyl, Arylaminocarbonyl, Aryl-(CrC5)-alkylaminocarbonyl stehen, (Ci-Cr>) alkoxycarbonyl, (C3-C6) cycloalkoxycarbonyl, (C3-C6) cycloalkyl (d-CsJ-alkoxycarbonyl, Aryioxycarbonyl, aryl (CrCr>) -alkoxycarbonyl, (C2-C5) - alkenyloxycarbonyl , (C2-C5) -alkynyloxycarbonyl, aminocarbonyl, (C1-C5) -alkylaminocarbonyl, bis [(Ci-C5) -alkyl] aminocarbonyl, (Ci-Cr,) - alkyl [(Ci-C5) -alkyl] aminocarbonyl, (Ci-Cr>) alkyl [(Ci-C5) alkoxy] aminocarbonyl, (C2-C5) - alkenylaminocarbonyl, (Cs-CeJ-cycloalkylaminocarbonyl, arylaminocarbonyl, aryl (CRC5) alkylaminocarbonyl stand,
A5 für S (Schwefel), O (Sauerstoff) oder die Gruppierungen N-H, N-CH3, N-CH2CH3, N- CH(CH3)2, N-C02t-Bu, N-Aryl, N-Heteroaryl, N-Heterocyclyl steht, A 5 represents S (sulfur), O (oxygen) or the groupings NH, N-CH 3 , N-CH 2 CH 3 , N-CH (CH 3 ) 2 , N-CO 2 t-Bu, N-aryl, N-heteroaryl, N-heterocyclyl is
R13, R14, R17 und R18 unabhängig voneinander für Wasserstoff, (d-CsJ-Alkyl, Fluor, Chlor, Brom, lod, (C3-C6)-Cycloalkyl, gegebenenfalls substituiertes Phenyl, Heteroaryl, Heterocyclyl, (C2-C5)-Alkenyl, Aryl-(CrC5)-alkyl, (Ci-C5)-Alkoxy,
(Ci-C5)-Alkoxy-(Ci-C5)-alkoxy, (Ci-C5)-Alkoxy-(Ci-C5)-alkyl, Hydroxy, (C1-C5)- Haloalkyl, (CrCr -Haloalkylthio stehen oder R 13 , R 14 , R 17 and R 18 independently of one another represent hydrogen, (C 1 -C 6 -alkyl, fluorine, chlorine, bromine, iodine, (C 3 -C 6) -cycloalkyl, optionally substituted phenyl, heteroaryl, heterocyclyl, (C 2 -C 5) alkenyl, aryl (-C 5) alkyl, (Ci-C 5) alkoxy, (C 1 -C 5 ) -alkoxy- (C 1 -C 5 ) -alkoxy, (C 1 -C 5 ) -alkoxy- (C 1 -C 5 ) -alkyl, hydroxy, (C 1 -C 5 ) -haloalkyl, (C 1 -C 6 -haloalkylthio) or
R13 und R17 mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls weiter substituierten 5 bis 7-gliedrigen Ring bilden, R 13 and R 17 with the atoms to which they are attached form a completely saturated or partially saturated, optionally further substituted 5 to 7-membered ring,
A6, A7 gleich oder verschieden sind und unabhängig voneinander für O (Sauerstoff), S (Schwefel), N-H, N-OCH3, N-CH3 oder die Gruppierung CR15R16 stehen, wobei jedoch in keinem Fall zwei N-, O- oder S-Atome benachbart sind, und wobei R15 und R16 in der Gruppierung CR15R16 jeweils gleiche oder verschiedene A 6 , A 7 are identical or different and independently of one another are O (oxygen), S (sulfur), NH, N-OCH 3, N-CH 3 or the group CR 15 R 16 , but in no case are two N , O or S atoms are adjacent, and wherein R 15 and R 16 in the group CR 15 R 16 are each the same or different
Bedeutungen gemäß der nachstehenden Definition haben und Have meanings as defined below and
R15 und R16 unabhängig voneinander für Wasserstoff, Fluor, Chlor, Brom, lod, (C1-C5)- Alkyl, gegebenenfalls substituiertes Phenyl, Heteroaryl, Heterocyclyl, (Ca-Ce)- Cycloalkyl, (C2-C5)-Alkenyl, (CrC5)-Alkoxy, (Ci-C5)-Alkoxy-(Ci-C5)-alkyl, R 15 and R 16 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, (C 1 -C 5 ) -alkyl, optionally substituted phenyl, heteroaryl, heterocyclyl, (C 1 -C 6) -cycloalkyl, (C 2 -C 5 ) -alkenyl , (C 1 -C 5 ) -alkoxy, (C 1 -C 5 ) -alkoxy- (C 1 -C 5 ) -alkyl,
(CrC5)-Haloalkoxy, (Ci-C5)-Haloalkyl, (Ci-C5)-Alkylthio, (CrC5)-Haloalkylthio, (Ci-C5)-Alkylthio-(Ci-C5)-alkyl, Hydroxycarbonyl, (Ci-Cs)-Alkoxycarbonyl, (C3-C6)-Cycloalkoxycarbonyl, Aryl-(Ci-C5)-alkoxycarbonyl, (C2-C5)- Alkenyloxycarbonyl, Aminocarbonyl, (Ci-C5)-Alkylaminocarbonyl, Bis[(Ci-Cs)- alkyljaminocarbonyl, (Ci-Cr>)-Alkyl[(Ci-Cr))-Alkyl]aminocarbonyl, (C2-C5)- Alkenylaminocarbonyl, (Ca-CeJ-Cycloalkylaminocarbonyl, Aryl-(Ci-Cs)- alkylaminocarbonyl, Amino, (Ci-C-5)-Alkylamino, (C3-C6)-Cycloalkylamino, Bis- [(d-C5)-Alkyl]amino stehen, (CrC 5) haloalkoxy, (Ci-C5) haloalkyl, (Ci-C 5) alkylthio, (CrC 5) haloalkylthio, (Ci-C5) alkylthio (Ci-C5) alkyl, hydroxycarbonyl, (C 1 -C 5) -alkoxycarbonyl, (C 3 -C 6) -cycloalkoxycarbonyl, aryl- (C 1 -C 5) -alkoxycarbonyl, (C 2 -C 5) -alkenyloxycarbonyl, aminocarbonyl, (C 1 -C 5) -alkylaminocarbonyl, bis [(C 1 -C -sol ) - alkyljaminocarbonyl, (Ci-Cr>) alkyl [(Ci-Cr)) - alkyl] aminocarbonyl, (C2-C5) - alkenylaminocarbonyl, (Ca-CeJ-cycloalkylaminocarbonyl, aryl (Ci-Cs) - alkylaminocarbonyl, amino , (C 1 -C 5) -alkylamino, (C 3 -C 6) -cycloalkylamino, bis- [(C 1 -C 5) -alkyl] -amino,
R19, R20, R22 und R23 unabhängig voneinander für Wasserstoff, (Ci-Cr,)-Alkyl, Fluor, Chlor, Brom, lod, (Ca-CeJ-Cycloalkyl, gegebenenfalls substituiertes Phenyl, Heteroaryl, Heterocyclyl, (C2-C5)-Alkenyl, Aryl-(Ci-C5)-alkyl, (Ci-C5)-Alkoxy, (Ci-Cs)-Haloalkyl stehen, R 19 , R 20 , R 22 and R 23 are each independently hydrogen, (Ci-Cr,) - alkyl, fluorine, chlorine, bromine, iodine, (Ca-CeJ-cycloalkyl, optionally substituted phenyl, heteroaryl, heterocyclyl, (C 2 -C 5) alkenyl, aryl (Ci-C 5) alkyl, (Ci-C 5) alkoxy, (Ci-Cs) -haloalkyl stand,
A8 für O (Sauerstoff), S (Schwefel), N-H, N-CH3, N-OCH3 oder die Gruppierung CHR2 steht und wobei R21 in der Gruppierung CHR21 die Bedeutung gemäß der nachstehenden Definition hat,
R21 für Wasserstoff, Fluor, Chlor, Brom, lod, (Ci-Ce)-Alkyl, gegebenenfalls A 8 is O (oxygen), S (sulfur), NH, N-CH 3 , N-OCH 3 or the moiety CHR 2 and wherein R 21 in the moiety CHR 21 has the meaning as defined below, R 21 is hydrogen, fluorine, chlorine, bromine, iodine, (C 1 -C 6) -alkyl, if appropriate
substituiertes Phenyl, Heteroaryl, Heterocyclyl, (Ca-Ce Cycloalkyl, (Cz-Ce)- Alkenyl, (Ci-C6)-Alkoxy, (Ci-Ce)-Haloalkoxy, (CrC6)-Haloalkyl, (CrC6)-Alkylthio, (CrCeJ-Haloalkylthio, Hydroxycarbonyl, Aryl-(Ci-Cr,)-alkoxycarbonyl, (C2-Cr,)- Alkenyloxycarbonyl, Aminocarbonyl, (d-CeJ-Alkylaminocarbonyl, Bis[(d-C6)- alkyl]aminocarbonyl, (CrC6)-Alkyl[(Ci-C6)-Alkyl]aminocarbonyl, (d-Ce)- Alkyl[(CrC6)-Alkoxy]aminocarbonyl, (C2-Cö)-Alkenylaminocarbonyl, (Ca-Ce)- Cycloalkylaminocarbonyl, Aryl-(Ci-C6)-alkylaminocarbonyl, Amino, (Ci-Ce)- Alkylamino, (Ca-CeJ-Cycloalkylamino, Bis[(Ci-C6)-Alkyl]amino steht, substituted phenyl, heteroaryl, heterocyclyl, (Ca-Ce cycloalkyl, (Cz-Ce) -alkenyl, (Ci-C 6 ) -alkoxy, (Ci-Ce) -haloalkoxy, (CrC 6 ) -haloalkyl, (CrC 6 ) - Alkylthio, (C 1 -C 6 -alkylthio, hydroxycarbonyl, aryl- (C 1 -C 8) -alkoxycarbonyl, (C 2 -C 8) -alkenyloxycarbonyl, aminocarbonyl, (C 1 -C 6 -alkylaminocarbonyl, bis [(C 1 -C 6) -alkyl] aminocarbonyl, (C 1 -C 6) -alkyl [(C 1 -C 6) -alkyl] aminocarbonyl, (C 1 -C 6) -alkyl [(C 1 -C 6) -alkoxy] -aminocarbonyl, (C 2 -C 6) -alkenylaminocarbonyl, (C 1 -C 6) -cycloalkylaminocarbonyl, arylcarboxylic (C 1 -C 6) -alkylaminocarbonyl, amino, (C 1 -C 6) -alkylamino, (C 1 -C 12 -cycloalkylamino, bis [(C 1 -C 6) -alkyl] -amino,
R24, R25, R26, R28, R29 und R30 unabhängig voneinander für Wasserstoff, (CrC5)-Alkyl, Fluor, Chlor, Brom, lod, (Ca-CeJ-Cycloalkyl, Aryl, Heteroaryl, Heterocyclyl, (C2-C5)-Alkenyl, (Ci-C5)-Alkoxy, (Ci-C5)-Haloalkyl, (CrC5)-Alkylthio, (C1-C5)- Haloalkylthio stehen, R 24 , R 25 , R 26 , R 28 , R 29 and R 30 independently of one another represent hydrogen, (C 1 -C 5 ) -alkyl, fluorine, chlorine, bromine, iodine, (C 1 -C 6 -cycloalkyl, aryl, heteroaryl, heterocyclyl, (C 2 -C 5) alkenyl, (Ci-C 5) alkoxy, (Ci-C5) haloalkyl, (CrC 5) alkylthio, (C1-C5) - haloalkylthio stand,
A9 für O (Sauerstoff), S (Schwefel), N-H, N-CH3, N-OCH3 oder die Gruppierung CHR27 steht und wobei R27 in der Gruppierung CHR27 die Bedeutung gemäß der nachstehenden Definition hat und R27 für Wasserstoff, Fluor, Chlor, Brom, lod, (Ci-Cs)-Alkyl, gegebenenfalls A 9 is O (oxygen), S (sulfur), NH, N-CH 3 , N-OCH 3 or the moiety CHR 27 and wherein R 27 in the moiety CHR 27 has the meaning defined below and R 27 is hydrogen , Fluorine, chlorine, bromine, iodine, (C 1 -C 8) -alkyl, if appropriate
substituiertes Phenyl, Heteroaryl, Heterocyclyl, (C-3-C6)-Cycloalkyl, (C2-C13)- Alkenyl, (Ci-C6)-Alkoxy, (Ci-C5)-Alkoxy-(Ci-C5)-alkyl, (Ci-C5)-Haloalkoxy, substituted phenyl, heteroaryl, heterocyclyl, (C 3 -C 6 ) -cycloalkyl, (C 2 -C 13) -alkenyl, (C 1 -C 6 ) -alkoxy, (C 1 -C 5 ) -alkoxy- (C 1 -C 5 ) - alkyl, (C 1 -C 5 ) -haloalkoxy,
(Ci-Cr>)-Haloalkyl, (CrC5)-Alkylthio, (Ci-C5)-Haloalkylthio, Hydroxycarbonyl, (Ci-C >)-Alkoxycarbonyl, (C3-C6)-Cycloalkoxycarbonyl, Aryl-(Ci-Cs)- alkoxycarbonyl, Aminocarbonyl, (Ci-C5)-Alkylaminocarbonyl, Bis[(Ci-Cs)- alkyljaminocarbonyl, (C3-Cc>)-Cycloalkylaminocarbonyl, Aryl-(d-C6)- alkylaminocarbonyl, Amino, (Ci-Cö)-Alkylamino, (C3-C6)-Cycloalkylamino, Bis[(Ci-C5)-Alkyl]amino steht. Im Speziellen bevorzugt sind Verbindungen der allgemeinen Formel (I), die durch die Formeln (la) bis (Ic) beschrieben werden,
(Ci-Cr>) -haloalkyl, (CrC 5) alkylthio, (Ci-C 5) haloalkylthio, hydroxycarbonyl, (Ci-C>) alkoxycarbonyl, (C3-C6) cycloalkoxycarbonyl, aryl (Ci-Cs ) - alkoxycarbonyl, aminocarbonyl, (Ci-C5) alkylaminocarbonyl, bis [(Ci-Cs) - alkyljaminocarbonyl, (C3-Cc>) cycloalkylaminocarbonyl, aryl (d-C6) - alkylaminocarbonyl, amino, (Ci-COE) alkylamino, (C3-C6) cycloalkylamino, bis [(Ci-C 5) alkyl] amino is. Especially preferred are compounds of the general formula (I) which are described by the formulas (Ia) to (Ic)
steht, wobei R7, R8, R9, R10, R11, R12, R13, R14. R17, R18, R19, R20, R22, R23, R24, R25, R26, R28, R29 und R30 und A1 bis A9 jeweils die Bedeutung gemäß der nachstehenden Definitionen haben und wobei der Pfeil für eine Bindung zur jeweiligen Gruppierung C-R6 in den vorgenannten Formeln (la) bis (Ic) steht, für Hydroxy, Methoxy, Ethoxy, n-Propyloxy, Methylcarbonyloxy, wherein R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 . R 17 , R 18 , R 19 , R 20 , R 22 , R 23 , R 24 , R 25 , R 26 , R 28 , R 29 and R 30 and A 1 to A 9 each have the meaning as defined below, and where the arrow for a bond to the respective grouping CR 6 in the abovementioned formulas (Ia) to (Ic) is hydroxyl, methoxy, ethoxy, n-propyloxy, methylcarbonyloxy,
Ethylcarbonyloxy, n-Propylcarbonyloxy, i-Propylcarbonyloxy, n- Butylcarbonyloxy, sec-Butylcarbonyloxy, tert.-Butylcarbonyloxy, n- Pentylcarbonyloxy, Phenylcarbonyloxy, p-CI-Phenylcarbonyloxy, p- Methylphenylcarbonyloxy, p-Trifluormethylphenylcarbonyloxy, p- Methoxyphenylcarbonyloxy, o-CI-Phenylcarbonyloxy, o- Methylphenylcarbonyloxy, o-Trifluormethylphenylcarbonyloxy, o- Methoxyphenylcarbonyloxy, 2-Pyridylcarbonyloxy, 3-Pyridylcarbonyloxy, 4- Pyridylcarbonyloxy, 6-Trifluormethyl-3-Pyridylcarbonyloxy, 4-Chlor-3- Pyridylcarbonyloxy, Cyclopropylcarbonyloxy, Cyclobutylcarbonyloxy, Ethylcarbonyloxy, n-propylcarbonyloxy, i -propylcarbonyloxy, n-butylcarbonyloxy, sec-butylcarbonyloxy, tert -butylcarbonyloxy, n-pentylcarbonyloxy, phenylcarbonyloxy, p-CI-phenylcarbonyloxy, p-methylphenylcarbonyloxy, p-trifluoromethylphenylcarbonyloxy, p-methoxyphenylcarbonyloxy, o-CI Phenylcarbonyloxy, o-methylphenylcarbonyloxy, o-trifluoromethylphenylcarbonyloxy, o-methoxyphenylcarbonyloxy, 2-pyridylcarbonyloxy, 3-pyridylcarbonyloxy, 4-pyridylcarbonyloxy, 6-trifluoromethyl-3-pyridylcarbonyloxy, 4-chloro-3-pyridylcarbonyloxy, cyclopropylcarbonyloxy, cyclobutylcarbonyloxy,
Cyclopentylcarbonyloxy, Cyclohexylcarbonyloxy, Methoxycarbonyloxy, Ethoxycarbonyloxy, Trimethylsilyloxy, Triethylsilyloxy, Triisopropylsilyloxy Dirne thylphenylsilyloxy, tert.-Butyldimethylsilyloxy steht,
für Hydroxycarbonyl, Methoxycarbonyl, Ethoxycarbonyl, n-Propyloxycarbonyl, iso-Propyloxycarbonyl, n-Butyloxycarbonyl, sec-Butyloxycarbonyl, tert.- Butyloxycarbonyl, n-Pentyloxycarbonyl, neo-Pentyloxycarbonyl, n- Hexyloxycarbonyl, Benzyloxycarbonyl, p-Chlorbenzyloxycarbonyl, p- Methoxybenzyloxycarbonyl, p-Fluorbenzyloxycarbonyl, p- Methylbenzyloxycarbonyl, Methoxyethoxycarbonyl, Ethoxyethoxycarbonyl, Ethoxymethoxycarbonyl, Methoxy-n-propyloxycarbonyl, Ethoxy-n- propoxycarbonyl, Cyclopropyloxycarbonyl, Cyclobutyloxycarbonyl, Cyclopentylcarbonyloxy, cyclohexylcarbonyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, trimethylsilyloxy, triethylsilyloxy, triisopropylsilyloxy, methylphenylsilyloxy, tert-butyldimethylsilyloxy, for hydroxycarbonyl, methoxycarbonyl, ethoxycarbonyl, n-propyloxycarbonyl, isopropyloxycarbonyl, n-butyloxycarbonyl, sec-butyloxycarbonyl, tert-butyloxycarbonyl, n-pentyloxycarbonyl, neo-pentyloxycarbonyl, n-hexyloxycarbonyl, benzyloxycarbonyl, p-chlorobenzyloxycarbonyl, p-methoxybenzyloxycarbonyl, p-fluorobenzyloxycarbonyl, p-methylbenzyloxycarbonyl, methoxyethoxycarbonyl, ethoxyethoxycarbonyl, ethoxymethoxycarbonyl, methoxy-n-propyloxycarbonyl, ethoxy-n-propoxycarbonyl, cyclopropyloxycarbonyl, cyclobutyloxycarbonyl,
Cyclopentyloxycarbonyl, Cyclohexyloxycarbonyl, (C2-C6)-alkinyloxycarbonyl, 2,2,-Difluorethoxycarbonyl, 2,2,2-Trifluorethoxycarbonyl, Methylaminocarbonyl, Ethylaminocarbonyl, n-Propylaminocarbonyl, iso-Propylaminocarbonyl, n- ButylaminocarbonyL iso-Butylaminocarbonyl, tert.-Butylaminocarbonyl, n- Pentylaminocarbonyl, neo-Pentylaminocarbonyl, iso-Pentylaminocarbonyl, Cyclopropylaminocarbonyl, Cyclobutylaminocarbonyl, Cyclopentyloxycarbonyl, cyclohexyloxycarbonyl, (C 2 -C 6) alkynyloxycarbonyl, 2,2'-difluoroethoxycarbonyl, 2,2,2-trifluoroethoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n -propylaminocarbonyl, iso -propylaminocarbonyl, n-butylaminocarbonyL iso-butylaminocarbonyl, tert -butylaminocarbonyl , n-pentylaminocarbonyl, neo-pentylaminocarbonyl, isopentylaminocarbonyl, cyclopropylaminocarbonyl, cyclobutylaminocarbonyl,
Cyclopentylaminocarbonyl, Cyclohexylaminocarbonyl, Piperidinyl-N-carbonyL Pyrrolidinyl-N-carbonyl, Cyanomethylaminocarbonyl, Cyanoethyiaminocarbonyl, Dimethylaminocarbonyl, Diethylaminocarbonyl, Diisopropylaminocarbonyl, Methoxyethylaminocarbonyl, Ethoxyethylaminocarbonyl, Formyl, Cyclopentylaminocarbonyl, cyclohexylaminocarbonyl, piperidinyl-N-carbonyl, pyrrolidinyl-N-carbonyl, cyanomethylaminocarbonyl, cyanoethylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, diisopropylaminocarbonyl, methoxyethylaminocarbonyl, ethoxyethylaminocarbonyl, formyl,
Hydroxyiminomethyl, Methoxyiminomethyl, Ethoxyiminomethyl, n- Propyloxyiminomethyl, iso-Propyloxyiminomethyl, n-Butyloxyiminomethyl, iso- Butyloxyiminomethyl, tert.-Butyloxyiminomethyl, Hydroxyiminomethyl, methoxyiminomethyl, ethoxyiminomethyl, n-propyloxyiminomethyl, iso-propyloxyiminomethyl, n-butyloxyiminomethyl, iso-butyloxyiminomethyl, tert-butyloxyiminomethyl,
Cyclopropylmethoxyiminomethyl, (C1-C5)- Alkylsulfonylaminocarbonyl, (C3-C5)- Cycloalkylsulfonylaminocarbonyl, (C3-C6)-Cycloalkyl-(CrC5)-alkoxycarbonyl, Aryloxycarbonyl, (C2-C5)-Alkenyloxycarbonyl, (C2-C5)-Alkinyloxycarbonyl,
(C2-C5)-Alkenyloxy-(CrC5)-alkoxycarbonyl, Cyclopropylmethoxyiminomethyl, (C 1 -C 5) -alkylsulfonylaminocarbonyl, (C 3 -C 5) -cycloalkylsulfonylaminocarbonyl, (C 3 -C 6) -cycloalkyl- (C 1 -C 5) -alkoxycarbonyl, aryloxycarbonyl, (C 2 -C 5) -alkenyloxycarbonyl, (C 2 -C 5) -alkynyloxycarbonyl, (C2-C5) alkenyloxy (CRC5) -alkoxycarbonyl
(Ci-C5)-Alkylamino-(Ci-C5)-alkoxycarbonyl, Tris[(Ci-C5)-alkyl]silyloxy-(Ci-C5)- alkoxycarbonyl, Bis[(Ci-C5)-Alkyl]amino-(Ci-C5)-alkoxycarbonyl, (C1-C5)- Alkyl[(Ci-C5)-alkyl]amino-(Ci-C5)-alkoxycarbonyl, Cyano-(Ci-Cs)- alkoxycarbonyl, Heterocyclyl-N-(Ci-C5)-alkoxycarbonyl, Heteroaryloxycarbonyl, Heteroaryl-(Ci-C5)-alkoxycarbonyl, Heterocyclyl-(Ci-C5)-alkoxycarbonyl, Heterocyclyloxycarbonyl, (C2-Cr,)-Alkenyl-(Ci-C5)-alkoxycarbonyl, (C2-C5)- Alkinyl-(d-C5)-alkoxycarbonyl, Aryl-(C2-Cr5)-alkinyloxycarbonyl, Aryl-(C2-Cs)- alkenyloxycarbonyl, Aminocarbonyl, (Ci-C5)-Alkyl[(Ci-C5)-Alkyl]aminocarbonyl, (Ci-C5)-Alkyl[(Ci-C5)-Alkoxy]aminocarbonyl, (C2-C5)-Alkenylaminocarbonyl,
(C3-C6)-Cycloalkylaminocarbonyl, Arylaminocarbonyl, Aryl-(Ci-Cs)- alkylaminocarbonyl, Heteroaryl-(Ci-Cr>)-alkylaminocarbonyl, (C1-C5)- Haloalkylaminocarbonyl, (C2-C5)-Alkinyl-(CrC5)-alkylaminocarbonyl, (C1-C5)- Alkoxycarbonylaminocarbonyl, Aryl-(Ci-Cr))-alkoxycarbonylaminocarbonyl, Hydroxycarbonyl-(CrC5)-alkyl, (Ci-C5)-Alkoxycarbonyl-(Ci-C5)-alkyl, (C3-C6)- Cycloalkoxycarbonyl-(CrC5)-alkyl, (C3-C6)-Cycloalkyl-(Ci-C5)-alkoxycarbonyl- (Ci-C5)-alkyl, (C2-C5)-Alkenyloxycarbonyl-(Ci-C5)-alkyl, Aryl-(CrC5)- alkoxycarbonyl-(d-C5)-alkyl, Aminosulfonyl, (Ci-C8)-Alkoxycarbonyl- heterocyclyl-N-carbonyi, (Ci-Ce)-Aikoxycarbonyl-(Ci-C8)-alkyl- heterocyclylidenaminocarbonyl, (Ci-C8)-Alkoxycarbonylheterocyclyliden-(Ci-C8)- alkylaminocarbonyl (Ci-C8)-Alkoxycarbonyl-(Ci-C8)-Alkyl((CrC8)- alkyl)aminocarbonyl, (d-C8)-Alkoxycarbonyl-(C3-C8)- cycloalkylidenaminocarbonyl, (Ci-C5)-Alkylaminocarbonyl-(Ci-C5)-alkyl, (C 1 -C 5 ) -alkylamino- (C 1 -C 5 ) -alkoxycarbonyl, tris [(C 1 -C 5 ) -alkyl] silyloxy- (C 1 -C 5 ) -alkoxycarbonyl, bis [(C 1 -C 5 ) -alkyl] -amino - (C 1 -C 5) -alkoxycarbonyl, (C 1 -C 5) -alkyl [(C 1 -C 5) -alkyl] amino- (C 1 -C 5) -alkoxycarbonyl, cyano- (C 1 -C 5) -alkoxycarbonyl, heterocyclyl-N- ( C 1 -C 5) -alkoxycarbonyl, heteroaryloxycarbonyl, heteroaryl- (C 1 -C 5) -alkoxycarbonyl, heterocyclyl- (C 1 -C 5) -alkoxycarbonyl, heterocyclyloxycarbonyl, (C 2 -C 18) -alkenyl- (C 1 -C 5) -alkoxycarbonyl, (C2 -C5) - alkynyl- (C 1 -C 5 ) -alkoxycarbonyl, aryl- (C 2 -Cr 5 ) -alkynyloxycarbonyl, aryl- (C 2 -C 5 ) -alkenyloxycarbonyl, aminocarbonyl, (C 1 -C 5) -alkyl [(C 1 -C 5) Alkyl] aminocarbonyl, (C 1 -C 5) -alkyl [(C 1 -C 5) -alkoxy] aminocarbonyl, (C 2 -C 5) -alkenylaminocarbonyl, (C3-C6) cycloalkylaminocarbonyl, arylaminocarbonyl, aryl (Ci-Cs) - alkylaminocarbonyl, heteroaryl (Ci-Cr>) alkylaminocarbonyl, (C1-C5) - Haloalkylaminocarbonyl, (C2-C5) alkynyl (CRC5) -alkylaminocarbonyl, (C 1 -C 5 ) -alkoxycarbonylaminocarbonyl, aryl- (C 1 -C 8)) -alkoxycarbonylaminocarbonyl, hydroxycarbonyl- (C 1 -C 5 ) -alkyl, (C 1 -C 5 ) -alkoxycarbonyl- (C 1 -C 5 ) -alkyl, ( C 3 -C 6 ) - cycloalkoxycarbonyl- (C 1 -C 5) -alkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 5) -alkoxycarbonyl- (C 1 -C 5 ) -alkyl, (C 2 -C 5 ) -alkenyloxycarbonyl- C 1 -C 5 ) -alkyl, aryl- (C 1 -C 5 ) -alkoxycarbonyl- (C 1 -C 5 ) -alkyl, aminosulfonyl, (C 1 -C 8) -alkoxycarbonyl-heterocyclyl-N-carbonyl, (C 1 -C 6) -alkoxycarbonyl- C 1 -C 8) -alkyl-heterocyclylideneaminocarbonyl, (C 1 -C 8) -alkoxycarbonyl-heterocyclylidene- (C 1 -C 8) -alkylaminocarbonyl (C 1 -C 8) -alkoxycarbonyl- (C 1 -C 8) -alkyl ((C 1 -C 8) -alkyl) -aminocarbonyl, (i.e. -C 8) alkoxycarbonyl- (C 3 -C 8) -cycloalkylideneaminocarbonyl, (C 1 -C 5) -alkylaminocarbonyl- (C 1 -C 5) -alkyl,
Aminocarbonyl-(Ci-C5)-alkyl, Bis[(Ci-C5)-alkyl]aminocarbonyl-(CrC5)-alkyl, (C3-C5)-Cycloalkylaminocarbonyl-(Ci-C5)-alkyl, Aryl-(CrC5)-alkylaminocarbonyl- (d-Cr>)-alkyl, Heteroaryl-(Ci-Cr>)-alkylaminocarbonyl-(Ci-C5)-alkyl, Cyano- (Ci-C5)-alkylaminocarbonyl-(CrC5)-alkyl, (Ci-C5)-Haloalkylaminocarbonyl- (Ci-C5)-alkyl, (C2-C5)-Alkinyl-(Ci-C5)-alkylaminocarbonyl-(Ci-C5)-alkyl, (C3-C6)- Cycloalkyl-(Ci-C5)-alkylaminocarbonyl-(Ci-C5)-alkyl, (C1-C5)- Alkoxycarbonylaminocarbonyl-(Ci-C5)-alkyl, Aryl-(Ci-C5)- alkoxycarbonylaminocarbonyl-(Ci-C5)-alkyl, (Ci-C5)-Alkoxycarbonyl-(d-C5)- alkylaminocarbonyL Hydroxycarbonyl-(Ci-C5)-alkylaminocarbonyl, Aryl-(Ci-Cs)- alkoxycarbonyl-(CrC5)-alkylaminocarbonyl, Aminocarbonyl-(CrC5)- alkylaminocarbonyl, (Ci-C5)-Alkylaminocarbonyl-(Ci-C5)-alkylaminocarbonyl, (C3-C6)-Cycloalkylaminocarbonyl-(Ci-C5)-alkylaminocarbonyl, (Cs-Ce)- Cycloalkyl-(Ci-C5)-alkylaminocarbonyl, (C3-C6)-Cycloalkyl-(Ci-C5)- alkylaminocarbonyl-(Ci-C5)-alkyl, (C3-C6)-Cycloalkyl-(Ci-C5)- alkylaminocarbonyl-(Ci-Cr>)-alkylaminocarbonyl, (C2-C5)-Alkenyl-(Ci-Cs)- alkylaminocarbonyl, (C2-C5)-Alkenylaminocarbonyl-(Ci-C5)-alkyl, (C2-C5)- Alkenyl-(Ci-C5)-alkylaminocarbonyl-(Ci-C5)-alkyl, (CrC5)-Alkylcarbonyl, (C3-C6)- Cycloalkylcarbonyl, Arylcarbonyl, Formyl, Aminoiminomethyl, (C1-C5)- Alkylaminoiminomethyl, Bis[(Ci-C5)-alkyl]aminoiminomethyl, (C3-Ce)- Cycloalkoxyiminomethyl , Aryloximinomethyl, Aryl-(Ci-C5)-alkoxyiminomethyl, Aryl-(Ci-C5)-alkylaminoiminomethyl, (C2-C5)-Alkenyloxyiminomethyl,
Arylaminoiminomethyl, Arylsulfonylaminoiminomethyl, Hydroxyaminocarbonyl, (CrCr -Alkoxyaminocarbonyl, Aryl-(Ci-C6)-alkoxyaminocarbonyl steht, Aminocarbonyl- (C 1 -C 5) -alkyl, bis [(C 1 -C 5) -alkyl] aminocarbonyl- (C 1 -C 5) -alkyl, (C 3 -C 5) -cycloalkylaminocarbonyl- (C 1 -C 5) -alkyl, aryl- (C 1 -C 5) -alkyl alkylaminocarbonyl (d-Cr>) alkyl, heteroaryl (Ci-Cr>) alkylaminocarbonyl (Ci-C5) alkyl, cyano- (Ci-C5) alkylaminocarbonyl (CRC5) alkyl, (Ci-C5 ) -Haloalkylaminocarbonyl- (Ci-C 5) alkyl, (C2-C5) alkynyl (Ci-C5) alkylaminocarbonyl (Ci-C 5) alkyl, (C 3 -C 6) - cycloalkyl ( C 1 -C 5 -alkylaminocarbonyl- (C 1 -C 5 ) -alkyl, (C 1 -C 5 ) -alkoxycarbonylaminocarbonyl- (C 1 -C 5 ) -alkyl, aryl- (C 1 -C 5 ) -alkoxycarbonylaminocarbonyl- (C 1 -C 5 ) -alkyl , (C 1 -C 5) -alkoxycarbonyl- (C 1 -C 5) -alkylaminocarbonyL hydroxycarbonyl- (C 1 -C 5) -alkylaminocarbonyl, aryl- (C 1 -C 5) -alkoxycarbonyl- (C 1 -C 5) -alkylaminocarbonyl, aminocarbonyl- (C 1 -C 5) -alkylaminocarbonyl, (C 1 -C 5) -alkylaminocarbonyl- (C 1 -C 5) -alkylaminocarbonyl, (C 3 -C 6) -cycloalkylaminocarbonyl- (C 1 -C 5) -alkylaminocarbonyl, (C 1 -C 6) -cycloalkyl- (C 1 -C 5 ) -alkylaminocarbonyl, (C3-C6) cycloalkyl (Ci-C 5) - alkylaminocarbonyl (Ci-C 5) alkyl, (C 3 -C 6) -cycloalkyl- (Ci-C 5) - alkylaminocarbonyl (Ci-Cr>) alkylaminocarbonyl, (C2-C5) alkenyl (Ci-Cs) - alkylaminocarbonyl, (C2-C5) -Alkenylaminocarbonyl- (Ci- C5) alkyl, (C2-C5) - alkenyl, (Ci-C 5) alkylaminocarbonyl (Ci-C 5) alkyl, (CrC 5) alkylcarbonyl, (C 3 -C 6) - cycloalkylcarbonyl, arylcarbonyl, Formyl, aminoiminomethyl, (C 1 -C 5) -alkylaminoiminomethyl, bis [(C 1 -C 5) -alkyl] aminoiminomethyl, (C 3 -Ce) -cycloalkoxyiminomethyl, aryloximinomethyl, aryl- (C 1 -C 5) -alkoxyiminomethyl, aryl- C5) -alkylaminoiminomethyl, (C2-C5) -alkenyloxyiminomethyl, Arylaminoiminomethyl, arylsulfonylaminoiminomethyl, hydroxyaminocarbonyl, (CrCr-alkoxyaminocarbonyl, aryl- (Ci-C6) -alkoxyaminocarbonyl,
R7, R8, R9 und R10 unabhängig voneinander für Wasserstoff, Fluor, Chlor, Brom, lod,R 7 , R 8 , R 9 and R 10 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine,
Nitro, Amino, Cyano, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, sec-Butyl, tert- Butyl, Phenyl, Cyclopropyl, Cyclobutyl, Hydroxy, Methoxy, Ethoxy, Nitro, amino, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, phenyl, cyclopropyl, cyclobutyl, hydroxy, methoxy, ethoxy,
Trifluormethyl, Difluormethyl, Trifluormethoxy, Difluormethoxy, Hydrothio, Methylthio, Trifluormethylthio, Methoxycarbonyl, Ethoxycarbonyl, iso- Propyloxycarbonyl, n-Propyloxycarbonyl, iso-Propyloxycarbonyl, tert.- Butyloxycarbonyl stehen, Trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, hydrothio, methylthio, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, iso-propyloxycarbonyl, n-propyloxycarbonyl, iso-propyloxycarbonyl, tert-butyloxycarbonyl,
A1, A2, A3 und A4 gleich oder verschieden sind und unabhängig voneinander für N A 1 , A 2 , A 3 and A 4 are the same or different and are independently N
(Stickstoff) oder die Gruppierungen C-H, C-CH3, C-F, C-Cl, C-Br. C-l, C-OCF3, C-OCH3, C-CF3, C-CO2H, C-CO2CH3 stehen, wobei jedoch in keinem Fall mehr als zwei N-Atome benachbart sind, (Nitrogen) or the groups CH, C-CH 3 , CF, C-Cl, C-Br. Cl, C-OCF3, C-OCH3, C-CF 3, C-CO2H, C-CO2CH3 are, but in no case more than two N atoms are adjacent,
R11 und R12 unabhängig voneinander für Wasserstoff, Fluor, Chlor, Brom, lod, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, sec-Butyl, tert.-Butyl, Phenyl, Cyclopropyl, Cyclobutyl, Trifluormethyl, Difluormethyl, Methoxycarbonyl, Ethoxycarbonyl, iso- Propyloxycarbonyl, n-Propyloxycarbonyl, tert.-Butyloxycarbonyl stehen, R 11 and R 12 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, phenyl, cyclopropyl, cyclobutyl, trifluoromethyl , Di-propyloxycarbonyl, n-propyloxycarbonyl
A5 für S (Schwefel), O (Sauerstoff) oder die Gruppierungen N-H, N-CH3, N-CH2CH3, N- CH(CH3)2, N-C02t-Bu, N-Aryl, N-Heteroaryl, N-Heterocyclyl steht, A 5 for S (sulfur), O (oxygen) or the groupings NH, N-CH 3 , N-CH 2 CH 3 , N-CH (CH 3 ) 2 , N-CO 2 t-Bu, N-aryl, N-heteroaryl , N-heterocyclyl,
R13, R14, R17 und R18 unabhängig voneinander für Wasserstoff, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, Fluor, Chlor, Brom, lod, Trifluormethyl stehen oder R 13 , R 14 , R 17 and R 18 are independently hydrogen, methyl, ethyl, n-propyl, iso-propyl, n-butyl, fluorine, chlorine, bromine, iodine, trifluoromethyl or
R13 und R17 mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls weiter substituierten 5 bis 7-gliedrigen Ring bilden, R 13 and R 17 with the atoms to which they are attached form a completely saturated or partially saturated, optionally further substituted 5 to 7-membered ring,
A6, A7 gleich oder verschieden sind und unabhängig voneinander für O (Sauerstoff), S (Schwefel), N-H, N-OCH3, N-CH3 oder die Gruppierung CR15R16 stehen, wobei jedoch in keinem Fall zwei N-, O- oder S-Atome benachbart sind, und wobei R15
und R16 in der Gruppierung CR15R16 jeweils gleiche oder verschiedene A 6 , A 7 are identical or different and independently of one another are O (oxygen), S (sulfur), NH, N-OCH 3, N-CH 3 or the group CR 15 R 16 , but in no case are two N , O or S atoms are adjacent, and wherein R 15 and R 16 in the group CR 15 R 16 are each the same or different
Bedeutungen gemäß der nachstehenden Definition haben und Have meanings as defined below and
R15 und R16 unabhängig voneinander für Wasserstoff, Fluor, Chlor, Brom, lod, Methyl, Ethyl, n-Propyl, iso-Propyl, Phenyl, Methoxy, Ethoxy, Trifluormethyl, R 15 and R 16 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, phenyl, methoxy, ethoxy, trifluoromethyl,
Trifluormethoxy, Methylthio stehen, Trifluoromethoxy, methylthio,
R19, R20, R22 und R23 unabhängig voneinander für Wasserstoff, Methyl, Ethyl, n-Propyl, iso-Propyl, Fluor, Chlor, Brom, lod, Phenyl, Trifluormethyl stehen, R 19 , R 20 , R 22 and R 23 are each independently hydrogen, methyl, ethyl, n-propyl, iso-propyl, fluorine, chlorine, bromine, iodine, phenyl, trifluoromethyl,
A8 für O (Sauerstoff), S (Schwefel), N-H, N-CH3, N-OCH3 oder die Gruppierung CHR21 steht und wobei R21 in der Gruppierung CHR21 die Bedeutung gemäß der nachstehenden Definition hat, R21 für Wasserstoff, Fluor, Chlor, Brom, lod, Methyl, Ethyl, Methoxy, Ethoxy, A 8 is O (oxygen), S (sulfur), NH, N-CH 3 , N-OCH 3 or the moiety CHR 21 , and wherein R 21 in the moiety CHR 21 is as defined below, R 21 is Hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, methoxy, ethoxy,
Trifluormethyl, Trifluormethoxy, Methylthio, Phenyl, Hydroxycarbonyl, Trifluoromethyl, trifluoromethoxy, methylthio, phenyl, hydroxycarbonyl,
Benzyloxycarbonyl steht, Benzyloxycarbonyl stands,
R24, R25, R26, R28, R29 und R30 unabhängig voneinander für Wasserstoff, Methyl, Ethyl, n-Propyl, iso-Propyl, Fluor, Chlor, Brom, lod, Phenyl, Trifluormethyl, Methylthio stehen. R 24 , R 25 , R 26 , R 28 , R 29 and R 30 independently represent hydrogen, methyl, ethyl, n-propyl, iso-propyl, fluorine, chlorine, bromine, iodine, phenyl, trifluoromethyl, methylthio.
A9 für O (Sauerstoff), S (Schwefel), N-H, N-CH3, N-OCH3 oder die Gruppierung CHR27 steht und wobei R27 in der Gruppierung CHR27 die Bedeutung gemäß der nachstehenden Definition hat und A 9 is O (oxygen), S (sulfur), NH, N-CH 3 , N -OCH 3 or the moiety CHR 27 and wherein R 27 in the moiety CHR 27 has the meaning as defined below and
R27 für Wasserstoff, Fluor, Chlor, Brom, lod, Methyl, Ethyl, Methoxy, Ethoxy, R 27 represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, methoxy, ethoxy,
Trifluormethyl, Trifluormethoxy, Methylthio, Hydroxycarbonyl, Methoxycarbonyl, Ethoxycarbonyl steht. Trifluoromethyl, trifluoromethoxy, methylthio, hydroxycarbonyl, methoxycarbonyl, ethoxycarbonyl.
Im Hinblick auf die erfindungsgemäßen Verbindungen werden die vorstehend und weiter unten verwendeten Bezeichnungen erläutert. Diese sind dem Fachmann geläufig und haben insbesondere die im Folgenden erläuterten Bedeutungen:
Erfindungsgemäß steht "Arylsulfonyl" für gegebenenfalls substituiertes Phenylsulfonyl oder gegebenenfalls substituiertes polycyclisches Arylsulfonyl, hier insbesondere gegebenenfalls substituiertes Naphthyl-sulfonyl, beispielsweise substituiert durch Fluor, Chlor, Brom, lod, Cyano, Nitro, Alkyl-, Haloalkyl-, Haloalkoxy-, Amino-, With regard to the compounds according to the invention, the terms used above and below are explained. These are familiar to the person skilled in the art and in particular have the meanings explained below: According to the invention "arylsulfonyl" is optionally substituted phenylsulfonyl or optionally substituted polycyclic arylsulfonyl, here in particular optionally substituted naphthylsulfonyl, for example substituted by fluorine, chlorine, bromine, iodine, cyano, nitro, alkyl, haloalkyl, haloalkoxy, amino,
Alkylamino-, Alkylcarbonylamino-, Dialkylamino- oder Alkoxy-gruppen. Alkylamino, alkylcarbonylamino, dialkylamino or alkoxy groups.
Erfindungsgemäß steht "Cycloalkylsulfonyl" - in Alleinstellung oder als Bestandteil einer chemischen Gruppe - für gegebenenfalls substituiertes Cycloalkylsulfonyl, vorzugsweise mit 3 bis 6 Kohlenstoffatomen wie beispielsweise Cyclopropylsulfonyl, Cyclobutylsulfonyl, Cyclopentylsulfonyl oder Cyclohexylsulfonyl. According to the invention "cycloalkylsulfonyl" - alone or as part of a chemical group - is optionally substituted Cycloalkylsulfonyl, preferably having 3 to 6 carbon atoms such as cyclopropylsulfonyl, cyclobutylsulfonyl, cyclopentylsulfonyl or cyclohexylsulfonyl.
Erfindungsgemäß steht "Alkylsulfonyl" - in Alleinstellung oder als Bestandteil einer chemischen Gruppe - für geradkettiges oder verzweigtes Alkylsulfonyl, vorzugsweise mit 1 bis 8, oder mit 1 bis 6 Kohlenstoffatomen wie beispielsweise Methylsulfonyl, Ethylsuifonyl, n-Propylsulfonyl, Isopropylsulfonyl, n-Butylsulfonyl, Isobutylsulfonyl, sec- Butylsulfonyl und tert-Butylsulfonyl. According to the invention "alkylsulfonyl" - alone or as part of a chemical group - is straight-chain or branched alkylsulfonyl, preferably having 1 to 8, or having 1 to 6 carbon atoms such as methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl , sec-butylsulfonyl and tert-butylsulfonyl.
Erfindungsgemäß steht "Heteroarylsulfonyl" für gegebenenfalls substituiertes According to the invention "heteroarylsulfonyl" is optionally substituted
Pyridylsulfonyl, Pyrimidinylsulfonyl, Pyrazinylsulfonyl oder gegebenenfalls Pyridylsulfonyl, pyrimidinylsulfonyl, pyrazinylsulfonyl or optionally
substituiertes polycyclisches Heteroarylsulfonyl, hier insbesondere gegebenenfalls substituiertes Chinolinylsulfonyl, beispielsweise substituiert durch Fluor, Chlor, Brom, lod, Cyano, Nitro, Alkyl-, Haloalkyl-, Haloalkoxy-, Amino-, Alkylamino-, substituted polycyclic heteroarylsulfonyl, here in particular optionally substituted quinolinylsulfonyl, for example substituted by fluorine, chlorine, bromine, iodine, cyano, nitro, alkyl, haloalkyl, haloalkoxy, amino, alkylamino,
Alkylcarbonylamino-, Dialkylamino- oder Alkoxygruppen. Erfindungsgemäß steht "Alkylthio" - in Alleinstellung oder als Bestandteil einer chemischen Gruppe - für geradkettiges oder verzweigtes S-Alkyl, vorzugsweise mit 1 bis 8, oder mit 1 bis 6 Kohlenstoffatomen, wie beispielsweise Methylthio, Ethylthio, n- Propylthio, Isopropylthio, n-Butylthio, Isobutylthio, sec-Butylthio und tert-Butylthio. Alkenylthio bedeutet ein über ein Schwefelatom gebundenen Alkenylrest, Alkinylthio bedeutet ein über ein Schwefelatom gebundenen Alkinylrest, Cycloalkylthio bedeutet ein über ein Schwefelatom gebundenen Cycloalkylrest und Cycloalkenylthio bedeutet ein über ein Schwefelatom gebundenen Cycloalkenylrest.
„Alkoxy" bedeutet ein über ein Sauerstoffatom gebundenen Alkylrest, Alkenyloxy bedeutet ein über ein Sauerstoffatom gebundenen Alkenylrest, Alkinyloxy bedeutet ein über ein Sauerstoffatom gebundenen Alkinylrest, Cycloalkyloxy bedeutet ein über ein Sauerstoffatom gebundenen Cycloaikylrest und Cycloalkenyloxy bedeutet ein über ein Sauerstoffatom gebundenen Cycloalkenylrest. Alkylcarbonylamino, dialkylamino or alkoxy groups. According to the invention, "alkylthio" - alone or as part of a chemical group - represents straight-chain or branched S-alkyl, preferably having 1 to 8, or having 1 to 6 carbon atoms, such as, for example, methylthio, ethylthio, n-propylthio, isopropylthio, n- Butylthio, isobutylthio, sec-butylthio and tert-butylthio. Alkenylthio represents an alkenyl radical bonded via a sulfur atom, alkynylthio represents an alkynyl radical bonded via a sulfur atom, cycloalkylthio represents a cycloalkyl radical bonded via a sulfur atom, and cycloalkenylthio represents a cycloalkenyl radical bonded via a sulfur atom. "Alkoxy" means an alkyl radical bonded through an oxygen atom, alkenyloxy represents an alkynyl radical bonded via an oxygen atom, alkynyloxy represents an alkynyl radical bonded via an oxygen atom, cycloalkyloxy denotes a cycloalkyl radical bonded via an oxygen atom, and cycloalkenyloxy denotes a cycloalkenyl radical bonded via an oxygen atom.
Der Begriff„Aryl" bedeutet ein gegebenenfalls substituiertes mono-, bi- oder polycyclisches aromatisches System mit vorzugsweise 6 bis 14, insbesondere 6 bis 10 Ring-C-Atomen, beispielsweise Phenyl, Naphthyl, Anthryl, Phenanthrenyl, und ähnliches, vorzugsweise Phenyl. The term "aryl" means an optionally substituted mono-, bi- or polycyclic aromatic system having preferably 6 to 14, in particular 6 to 10 ring C atoms, for example phenyl, naphthyl, anthryl, phenanthrenyl, and the like, preferably phenyl.
Vom Begriff„gegebenenfalls substituiertes Aryl" sind auch mehrcyclische Systeme, wie Tetrahydronaphtyl, Indenyl, Indanyl, Fluorenyl, Biphenylyl, umfasst, wobei die Bindungsstelle am aromatischen System ist. Von der Systematik her ist„Aryl" in der Regel auch von dem Begriff„gegebenenfalls substituiertes Phenyl" umfasst. The term "optionally substituted aryl" also includes polycyclic systems, such as tetrahydronaphthyl, indenyl, indanyl, fluorenyl, biphenylyl, the binding site being on the aromatic system. "Aryl" is also generally known from the term "optionally substituted phenyl ".
Bevorzugte Aryl-Substituenten sind hier zum Beispiel Wasserstoff, Halogen, Alkyl, Cycloalkyl, Cycloalkylalkyl, Cycloalkenyl, Halocycloalkyl, Alkenyl, Alkinyl, Aryl, Preferred aryl substituents here are, for example, hydrogen, halogen, alkyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, halocycloalkyl, alkenyl, alkynyl, aryl,
Arylalkyl, Arylalkenyl, Heteroaryl, Heteroarylalkyl, Heterocyclyl, Heterocyclylalkyl, Alkoxyalkyl, Alkylthio, Haloalkylthio, Haloalkyl, Alkoxy, Haloalkoxy, Cycloalkoxy, Cycloalkylalkoxy, Aryloxy, Heteroraryloxy, Alkoxyalkoxy, Alkinylalkoxy, Alkenyloxy, Bis- alkylaminoalkoxy, Tris-[alkyl]silyl, Bis-[alkyl]arylsilyl, Bis-[alkyl]alkylsilyl, Tris- [alkyijsilylalkinyl, Arylalkinyl, Heteroarylalkinyl, Alkylalkinyl, Cycloalkylalkinyl, Arylalkyl, arylalkenyl, heteroaryl, heteroarylalkyl, heterocyclyl, heterocyclylalkyl, alkoxyalkyl, alkylthio, haloalkylthio, haloalkyl, alkoxy, haloalkoxy, cycloalkoxy, cycloalkylalkoxy, aryloxy, heteroaryloxy, alkoxyalkoxy, alkynylalkoxy, alkenyloxy, bisalkylaminoalkoxy, tris [alkyl] silyl, bis [alkyl] arylsilyl, bis [alkyl] alkylsilyl, tris [alkylsilylalkynyl, arylalkynyl, heteroarylalkynyl, alkylalkynyl, cycloalkylalkynyl,
Haloalkylalkinyl, Heterocyclyl-N-alkoxy, Nitro, Cyano, Amino, Alkylamino, Bis- alkylamino, Alkylcarbonylamino, Cycloalkylcarbonylamino, Arylcarbonylamino, Alkoxy carbonylamino, Alkoxycarbonylalkylamino, Arylalkoxycarbonylalkylamino, Hydroxycarbonyl, Alkoxycarbonyl, Aminocarbonyl, Alkylaminocarbonyl, Haloalkylalkynyl, heterocyclyl-N-alkoxy, nitro, cyano, amino, alkylamino, bisalkylamino, alkylcarbonylamino, cycloalkylcarbonylamino, arylcarbonylamino, alkoxycarbonylamino, alkoxycarbonylalkylamino, arylalkoxycarbonylalkylamino, hydroxycarbonyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl,
Cycloalkylaminocarbonyl, Bis-Alkylaminocarbonyl, Heteroarylalkoxy, Arylalkoxy Cycloalkylaminocarbonyl, bis-alkylaminocarbonyl, heteroarylalkoxy, arylalkoxy
Ein heterocyclischer Rest (Heterocyclyl) enthält mindestens einen heterocyclischen Ring (=carbocyclischer Ring, in dem mindestens ein C-Atom durch ein Heteroatom ersetzt ist, vorzugsweise durch ein Heteroatom aus der Gruppe N, O, S, P) der gesättigt, ungesättigt, teilgesättigt oder heteroaromatisch ist und dabei unsubstituiert oder substituiert sein kann, wobei die Bindungsstelle an einem Ringatom lokalisiert ist. Ist der Heterocyclylrest oder der heterocyclische Ring gegebenenfalls substituiert,
kann er mit anderen carbocyclischen oder heterocyclischen Ringen annelliert sein. Im Falle von gegebenenfalls substituiertem Heterocyclyl werden auch mehrcyclische Systeme umfaßt, wie beispielsweise 8-Aza-bicyclo[3.2.1 ]octanyl, 8-Aza- bicyclo[2.2.2]octanyl oder 1 -Aza-bicyclo[2.2.1 jheptyl. im Falle von gegebenenfalls substituiertem Heterocyclyl werden auch spirocyclische Systeme umfaßt, wie beispielsweise 1 -Oxa-5-aza-spiro[2.3]hexyl. Wenn nicht anders definiert, enthält der heterocyclische Ring vorzugsweise 3 bis 9 Ringatome, insbesondere 3 bis 6 A heterocyclic radical (heterocyclyl) contains at least one heterocyclic ring (= carbocyclic ring in which at least one C atom is replaced by a heteroatom, preferably by a heteroatom from the group N, O, S, P) which is saturated, unsaturated, partially saturated or is heteroaromatic and may be unsubstituted or substituted, wherein the binding site is located on a ring atom. If the heterocyclyl radical or the heterocyclic ring is optionally substituted, it may be fused with other carbocyclic or heterocyclic rings. In the case of optionally substituted heterocyclyl, more cyclic systems are also included, for example 8-azabicyclo [3.2.1] octanyl, 8-azabicyclo [2.2.2] octanyl or 1-azabicyclo [2.2.1] -heptyl. in the case of optionally substituted heterocyclyl, spirocyclic systems are also included, such as 1-oxa-5-aza-spiro [2.3] hexyl. Unless defined otherwise, the heterocyclic ring preferably contains 3 to 9 ring atoms, especially 3 to 6
Ringatome, und ein oder mehrere, vorzugsweise 1 bis 4, insbesondere 1 , 2 oder 3 Heteroatome im heterocyclischen Ring, vorzugsweise aus der Gruppe N, O, und S, wobei jedoch nicht zwei Sauerstoffatome direkt benachbart sein sollen, wie Ring atoms, and one or more, preferably 1 to 4, in particular 1, 2 or 3 heteroatoms in the heterocyclic ring, preferably from the group N, O, and S, but not two oxygen atoms should be directly adjacent, as
beispielsweise mit einem Heteroatom aus der Gruppe N, O und S 1 - oder 2- oder 3- Pyrrolidinyl, 3,4-Dihydro-2H-pyrrol-2- oder 3-yl, 2, 3-Dihydro-1 H-pyrrol-1- oder 2- oderfor example, with a heteroatom from the group N, O and S 1 - or 2- or 3-pyrrolidinyl, 3,4-dihydro-2H-pyrrole-2 or 3-yl, 2, 3-dihydro-1 H-pyrrole 1- or 2- or
3- oder 4- oder 5-yl; 2,5-Dihydro-1 H-pyrrol-1 - oder 2- oder 3-yl, 1 - oder 2- oder 3- oder3- or 4- or 5-yl; 2,5-dihydro-1H-pyrrol-1 - or 2- or 3-yl, 1- or 2- or 3- or
4- Piperidinyl; 2.3.4,5-Tetrahydropyridin-2- oder 3- oder 4- oder 5-yl oder 6-yl; 1 ,2,3,6- Tetrahydropyhdin-1 - oder 2- oder 3- oder 4- oder 5- oder 6-yl; 1 ,2.3,4-4-piperidinyl; 2,3,4,5-tetrahydropyridine-2- or 3- or 4- or 5-yl or 6-yl; 1, 2,3,6-tetrahydropyhdin-1 - or 2- or 3- or 4- or 5- or 6-yl; 1, 2.3,4-
Tetrahydropyridin-1 - oder 2- oder 3- oder 4- oder 5- oder 6-yl; 1 ,4-Dihydropyridin-1 - oder 2- oder 3- oder 4-yl; 2,3-Dihydropyridin-2- oder 3- oder 4- oder 5- oder 6-yl; 2,5- Dihydropyridin-2- oder 3- oder 4- oder 5- oder 6-yl, 1 - oder 2- oder 3- oder 4-Azepanyl; 2.3,4,5-Tetrahydro-1 H-azepin-1 - oder 2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2.3,4,7-Tetrahydro-1 H-azepin-1 - oder 2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3,6,7-Tetrahydro-1 H-azepin-1 - oder 2- oder 3- oder 4-yl; 3,4,5.6-Tetrahydro-2H- azepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 4,5-Dihydro-1 H-azepin-1 - oder 2- oder 3- oder 4-yl; 2,5-Dihydro-1 H-azepin-1 - oder -2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,7-Dihydro-1 H-azepin-1 - oder -2- oder 3- oder 4-yl; 2,3-Dihydro-1 H-azepin- 1 - oder -2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 3.4-Dihydro-2H-azepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 3.6-Dihydro-2H-azepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 5.6-Dihydro-2H-azepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 4,5-Dihydro-3H-azepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 1 H-Azepin-1 - oder -2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2H-Azepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 3H-Azepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 4H-Azepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl, 2- oder 3-Oxolanyl (= 2- oder 3-Tetrahydrofuranyl); 2.3- Di hyd rof u ra n-2- oder 3- oder 4- oder 5-yl; 2,5-Dihydrofuran-2- oder 3-yl, 2- oder 3- oder 4-Oxanyl (= 2- oder 3- oder 4-Tetrahydropyranyl); 3.4-Dihydro-2H-pyran-2- oder 3- oder 4- oder 5- oder 6-yl; 3,6-Dihydro-2H-pyran-2- oder 3-oder 4- oder 5- oder 6-yl;
2H-Pyran-2- oder 3- oder 4- oder 5- oder 6-yl; 4H-Pyran-2- oder 3- oder 4-yl, 2- oder 3- oder 4-Oxepanyl; 2,3.4,5-Tetrahydrooxepin-2- oder 3- oder 4- oder 5- oder 6- oder 7- yl; 2,3,4,7-Tetrahydrooxepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yi: 2,3,6.7- Tetrahydrooxepin-2- oder 3- oder 4-yl; 2,3-Dihydrooxepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yi; 4,5-Dihydrooxepin-2- oder 3- oder 4-yl; 2,5-Dihydrooxepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yi: Oxepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yi;Tetrahydropyridine-1 - or 2- or 3- or 4- or 5- or 6-yl; 1,4-dihydropyridine-1 - or 2- or 3- or 4-yl; 2,3-dihydropyridine-2- or 3- or 4- or 5- or 6-yl; 2,5-dihydropyridine-2- or 3- or 4- or 5- or 6-yl, 1- or 2- or 3- or 4-azepanyl; 2,3,4,5-tetrahydro-1H-azepine-1 - or 2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,7-tetrahydro-1H-azepine-1 - or 2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,6,7-tetrahydro-1H-azepine-1 - or 2- or 3- or 4-yl; 3,4,5,6-tetrahydro-2H-azepine-2 or 3 or 4 or 5 or 6 or 7-yl; 4,5-dihydro-1H-azepine-1 - or 2- or 3- or 4-yl; 2,5-dihydro-1H-azepine-1 or -2 or 3 or 4 or 5 or 6 or 7-yl; 2,7-dihydro-1H-azepine-1 - or -2- or 3- or 4-yl; 2,3-dihydro-1H-azepine-1 - or -2- or 3- or 4- or 5- or 6- or 7-yl; 3,4-dihydro-2H-azepine-2 or 3 or 4 or 5 or 6 or 7-yl; 3.6-dihydro-2H-azepine-2 or 3 or 4 or 5 or 6 or 7-yl; 5.6-dihydro-2H-azepine-2- or 3- or 4- or 5- or 6- or 7-yl; 4,5-dihydro-3H-azepine-2 or 3 or 4 or 5 or 6 or 7-yl; 1 H-azepine-1 or -2 or 3 or 4 or 5 or 6 or 7-yl; 2H-azepine-2- or 3- or 4- or 5- or 6- or 7-yl; 3H-azepine-2- or 3- or 4- or 5- or 6- or 7-yl; 4H-azepine-2- or 3- or 4- or 5- or 6- or 7-yl, 2- or 3-oxolanyl (= 2- or 3-tetrahydrofuranyl); 2.3- dihydrofuran-2- or 3- or 4- or 5-yl; 2,5-dihydrofuran-2- or 3-yl, 2- or 3- or 4-oxanyl (= 2- or 3- or 4-tetrahydropyranyl); 3,4-dihydro-2H-pyran-2 or 3 or 4 or 5 or 6-yl; 3,6-dihydro-2H-pyran-2 or 3 or 4 or 5 or 6-yl; 2H-pyran-2- or 3- or 4- or 5- or 6-yl; 4H-pyran-2- or 3- or 4-yl, 2- or 3- or 4-oxepanyl; 2,3,4,5-tetrahydrooxepin-2 or 3 or 4 or 5 or 6 or 7 yl; 2,3,4,7-tetrahydrooxepin-2 or 3 or 4 or 5 or 6 or 7-yl: 2,3,6,7-tetrahydrooxepin-2 or 3 or 4-yl; 2,3-dihydrooxepin-2 or 3 or 4 or 5 or 6 or 7-yi; 4,5-dihydrooxepin-2 or 3 or 4-yl; 2,5-dihydrooxepin-2 or 3 or 4 or 5 or 6 or 7-yi: oxepin-2 or 3 or 4 or 5 or 6 or 7-yi;
2- oder 3-Tetrahydrothiophenyl; 2,3-Dihydrothiophen-2- oder 3- oder 4- oder 5-yl; 2.5- Dihydrothiophen-2- oder 3-yl; Tetrahydro-2H-thiopyran-2- oder 3- oder 4-yl; 3,4- Dihydro-2H-thiopyran-2- oder 3- oder 4- oder 5- oder 6-yl; 3,6-Dihydro-2H-thiopyran- 2- oder 3- oder 4- oder 5- oder 6-yl; 2H-Thiopyran-2- oder 3- oder 4- oder 5- oder 6-yl; 4H-Thiopyran-2- oder 3- oder 4-yl. Bevorzugte 3-Ring und 4-Ring-Heterocyclen sind beispielsweise 1 - oder 2-Aziridinyl, Oxiranyl, Thiiranyl, 1 - oder 2- oder 3-Azetidinyl, 2- oder 3-Oxetanyl, 2- oder 3-Thietanyl, 1 ,3-Dioxetan-2-yl. Weitere Beispiele für 2- or 3-tetrahydrothiophenyl; 2,3-dihydrothiophene-2 or 3 or 4 or 5-yl; 2,5-dihydrothiophene-2 or 3-yl; Tetrahydro-2H-thiopyran-2- or 3- or 4-yl; 3,4-dihydro-2H-thiopyran-2 or 3 or 4 or 5 or 6-yl; 3,6-dihydro-2H-thiopyran-2 or 3 or 4 or 5 or 6-yl; 2H-thiopyran-2 or 3 or 4 or 5 or 6-yl; 4H-thiopyran-2- or 3- or 4-yl. Preferred 3-membered and 4-membered heterocycles are, for example, 1- or 2-aziridinyl, oxiranyl, thiiranyl, 1- or 2- or 3-azetidinyl, 2- or 3-oxetanyl, 2- or 3-thietanyl, 1,3 -Dioxetan-2-yl. Further examples of
"Heterocyclyl" sind ein partiell oder vollständig hydrierter heterocyclischer Rest mit zwei Heteroatomen aus der Gruppe N, O und S, wie beispielsweise 1 - oder 2- oder 3- oder 4-Pyrazolidinyl; 4.5-Dihydro-3H-pyrazol- 3- oder 4- oder 5-yl; 4,5-Dihydro-1 H- pyrazol-1- oder 3- oder 4- oder 5-yl; 2,3-Dihydro-1 H-pyrazol-1 - oder 2- oder 3- oder 4- oder 5-yl; 1 - oder 2- oder 3- oder 4- Imidazolidinyl; 2.3-Dihydro-1 H-imidazol-1 - oder 2- oder 3- oder 4-yl; 2,5-Dihydro-1 H-imidazol-1 - oder 2- oder 4- oder 5-yl; 4,5-Dihydro- 1 H-imidazol-1 - oder 2- oder 4- oder 5-yl; Hexahydropyridazin-1- oder 2- oder 3- oder 4-yl; 1 ,2,3,4-Tetrahydropyridazin-1 - oder 2- oder 3- oder 4- oder 5- oder 6-yl; 1 ,2.3,6- Tetrahydropyridazin-1 - oder 2- oder 3- oder 4- oder 5- oder 6-yl; 1 ,4,5.6- Tetrahydropyridazin-1 - oder 3- oder 4- oder 5- oder 6-yl; 3,4,5,6-Tetrahydropyridazin-"Heterocyclyl" are a partially or fully hydrogenated heterocyclic radical having two heteroatoms from the group N, O and S, such as 1- or 2- or 3- or 4-pyrazolidinyl; 4,5-dihydro-3H-pyrazole-3- or 4- or 5-yl; 4,5-dihydro-1H-pyrazole-1 or 3 or 4 or 5-yl; 2,3-dihydro-1H-pyrazole-1 - or 2- or 3- or 4- or 5-yl; 1- or 2- or 3- or 4-imidazolidinyl; 2,3-dihydro-1H-imidazole-1 - or 2- or 3- or 4-yl; 2,5-dihydro-1H-imidazole-1 - or 2- or 4- or 5-yl; 4,5-dihydro-1H-imidazole-1 - or 2- or 4- or 5-yl; Hexahydropyridazine-1 or 2- or 3- or 4-yl; 1,2,3,4-tetrahydropyridazine-1 - or 2- or 3- or 4- or 5- or 6-yl; 1, 2,3,6-tetrahydropyridazine-1 - or 2- or 3- or 4- or 5- or 6-yl; 1, 4,5,6-tetrahydropyridazine-1 - or 3- or 4- or 5- or 6-yl; 3,4,5,6-Tetrahydropyridazin-
3- oder 4- oder 5-yl; 4.5-Dihydropyridazin-3- oder 4-yl; 3,4-Dihydropyridazin-3- oder 4- oder 5- oder 6-yl; 3,6-Dihydropyridazin-3- oder 4-yl; 1 ,6-Dihydropyriazin-1 - oder 3- oder 4- oder 5- oder 6-yl; Hexahydropyrimidin-1 - oder 2- oder 3- oder 4-yl; 1 ,4.5.6- Tetrahydropyrimidin-1 - oder 2- oder 4- oder 5- oder 6-yl; 1 .2,5.6-Tetrahydropyrimidin- 1 - oder 2- oder 4- oder 5- oder 6-yl; 1 ,2,3.4-Tetrahydropyrimidin-1- oder 2- oder 3- oder 4- oder 5- oder 6-yl; 1 ,6-Dihydropyrimidin-1 - oder 2- oder 4- oder 5- oder 6-yl; 1 ,2-Dihydropyrimidin-1 - oder 2- oder 4- oder 5- oder 6-yl; 2,5-Dihydropyrimidin-2- oder3- or 4- or 5-yl; 4,5-dihydropyridazine-3 or 4-yl; 3,4-dihydropyridazine-3- or 4- or 5- or 6-yl; 3,6-dihydropyridazine-3 or 4-yl; 1,6-dihydropyriazine-1 - or 3- or 4- or 5- or 6-yl; Hexahydropyrimidine-1 - or 2- or 3- or 4-yl; 1, 4.5.6- tetrahydropyrimidine-1 - or 2- or 4- or 5- or 6-yl; 1, 2, 5, 6-tetrahydropyrimidin-1 - or 2- or 4- or 5- or 6-yl; 1, 2,3,4-tetrahydropyrimidine-1 or 2 or 3 or 4 or 5 or 6-yl; 1,6-dihydropyrimidine-1 - or 2- or 4- or 5- or 6-yl; 1,2-dihydropyrimidine-1 - or 2- or 4- or 5- or 6-yl; 2,5-dihydropyrimidine-2- or
4- oder 5-yl; 4.5-Dihydropyrimidin- 4- oder 5- oder 6-yl; 1 ,4-Dihydropyrimidin-1 - oder 2- oder 4- oder 5- oder 6-yl; 1- oder 2- oder 3-Piperazinyl; 1 ,2.3,6-Tetrahydropyrazin-1- oder 2- oder 3- oder 5- oder 6-yl; 1 ,2.3,4-Tetrahydropyrazin-1 - oder 2- oder 3- oder 4- oder 5- oder 6-yl; 1 ,2-Dihydropyrazin-1- oder 2- oder 3- oder 5- oder 6-yl; 1 ,4-
Dihydropyrazin-1 - oder 2- oder 3-yl; 2,3-Dihydropyrazin-2- oder 3- oder 5- oder 6-yl; 2,5-Dihydropyrazin-2- oder 3-yl; 1 ,3-Dioxolan-2- oder 4- oder 5-yl; 1 .3-Dioxol-2- oder 4-yl; 1 ,3-Dioxan-2- oder 4- oder 5-yl; 4H-1 ,3-Dioxin-2- oder 4- oder 5- oder 6-yl; 1 ,4- Dioxan-2- oder 3- oder 5- oder 6-yl; 2.3-Dihydro-1 ,4-dioxin-2- oder 3- oder 5- oder 6-yl; 1 ,4-Dioxin-2- oder 3-yl; 1 ,2-Dithiolan-3- oder 4-yl; 3H-1 ,2-Dithiol-3- oder 4- oder 5-yl;4- or 5-yl; 4,5-dihydropyrimidine-4- or 5- or 6-yl; 1,4-dihydropyrimidine-1 - or 2- or 4- or 5- or 6-yl; 1- or 2- or 3-piperazinyl; 1, 2,3,6-tetrahydropyrazine-1 or 2 or 3 or 5 or 6-yl; 1, 2,3,4-tetrahydropyrazine-1 - or 2- or 3- or 4- or 5- or 6-yl; 1,2-dihydropyrazine-1- or 2- or 3- or 5- or 6-yl; 1, 4- Dihydropyrazine-1 - or 2- or 3-yl; 2,3-dihydropyrazine-2- or 3- or 5- or 6-yl; 2,5-dihydropyrazine-2 or 3-yl; 1,3-dioxolane-2- or 4- or 5-yl; 1, 3-dioxol-2 or 4-yl; 1,3-dioxane-2- or 4- or 5-yl; 4H-1, 3-dioxin-2 or 4 or 5 or 6-yl; 1, 4-dioxane-2 or 3 or 5 or 6-yl; 2,3-dihydro-1,4-dioxin-2- or 3- or 5- or 6-yl; 1, 4-dioxin-2 or 3-yl; 1,2-dithiolan-3 or 4-yl; 3H-1,2-dithiol-3- or 4- or 5-yl;
1 .3- Dithiolan-2- oder 4-yl; 1 ,3-Dithiol-2- oder 4-yl; 1 ,2-Dithian-3- oder 4-yl; 3,4-Dihydro- 1 ,2-dithiin-3- oder 4- oder 5- oder 6-yl; 3,6-Dihydro-1 .2-dithiin-3- oder 4-yl; 1 ,2-Dithiin-1, 3-dithiolan-2 or 4-yl; 1,3-dithiol-2- or 4-yl; 1,2-dithian-3 or 4-yl; 3,4-dihydro-1,2-dithiin-3- or 4- or 5- or 6-yl; 3,6-dihydro-1, 2-dithiin-3 or 4-yl; 1, 2-dithinine
3- oder 4-yl; 1 ,3-Dithian-2- oder 4- oder 5-yl; 4H-1 ,3-Dithiin-2- oder 4- oder 5- oder 6- yl; lsoxazolidin-2- oder 3- oder 4- oder 5-yl; 2.3-Dihydroisoxazol-2- oder 3- oder 4- oder 5-yl; 2,5-Dihydroisoxazol-2- oder 3- oder 4- oder 5-yl; 4.5-Dihydroisoxazol-3- oder3- or 4-yl; 1,3-dithian-2- or 4- or 5-yl; 4H-1, 3-dithiine-2 or 4 or 5 or 6 yl; Isoxazolidine-2 or 3 or 4 or 5-yl; 2,3-dihydroisoxazole-2- or 3- or 4- or 5-yl; 2,5-dihydroisoxazole-2 or 3 or 4 or 5-yl; 4.5-dihydroisoxazole-3-Or
4- oder 5-yl; 1 ,3-Oxazolidin-2- oder 3- oder 4- oder 5-yl; 2.3-Dihydro-1 ,3-oxazol-2- oder4- or 5-yl; 1,3-oxazolidine-2- or 3- or 4- or 5-yl; 2,3-dihydro-1,3-oxazole-2-or
3- oder 4- oder 5-yl; 2,5-Dihydro-1 ,3-oxazol-2- oder 4- oder 5-yl; 4.5-Dihydro-1 ,3- oxazol-2- oder 4- oder 5-yl; 1 ,2-Oxazinan-2- oder 3- oder 4- oder 5- oder 6-yl; 3,4- Dihydro-2H-1 ,2-oxazin-2- oder 3- oder 4- oder 5- oder 6-yl; 3.6-Dihydro-2H-1 ,2-oxazin- 2- oder 3- oder 4- oder 5- oder 6-yl; 5,6-Dihydro-2H-1 ,2-oxazin-2- oder 3- oder 4- oder3- or 4- or 5-yl; 2,5-dihydro-1,3-oxazol-2- or 4- or 5-yl; 4,5-dihydro-1,3-oxazol-2 or 4 or 5-yl; 1, 2-oxazinan-2 or 3 or 4 or 5 or 6-yl; 3,4-dihydro-2H-1,2-oxazine-2- or 3- or 4- or 5- or 6-yl; 3.6-dihydro-2H-1,2-oxazine-2- or 3- or 4- or 5- or 6-yl; 5,6-dihydro-2H-1, 2-oxazine-2 or 3 or 4 or
5- oder 6-yl; 5,6-Dihydro-4H-1 ,2-oxazin-3- oder 4- oder 5- oder 6-yl; 2H-1 ,2-Oxazin-2- oder 3- oder 4- oder 5- oder 6-yl; 6H-1 ,2-Oxazin-3- oder 4- oder 5- oder 6-yl; 4H-1 .2- Oxazin-3- oder 4- oder 5- oder 6-yl; 1 ,3-Oxazinan-2- oder 3- oder 4- oder 5- oder 6-yl;5- or 6-yl; 5,6-dihydro-4H-1,2-oxazine-3- or 4- or 5- or 6-yl; 2H-1, 2-oxazine-2 or 3 or 4 or 5 or 6-yl; 6H-1, 2-oxazine-3 or 4 or 5 or 6-yl; 4H-1, 2-oxazine-3 or 4 or 5 or 6-yl; 1,3-oxazinan-2 or 3 or 4 or 5 or 6-yl;
3.4- Dihydro-2H-1 ,3-oxazin-2- oder 3- oder 4- oder 5- oder 6-yl; 3.6-Dihydro-2H-1 ,3- oxazin-2- oder 3- oder 4- oder 5- oder 6-yl; 5,6-Dihydro-2H-1 ,3-oxazin-2- oder 4- oder3,4-dihydro-2H-1,3-oxazine-2- or 3- or 4- or 5- or 6-yl; 3.6-dihydro-2H-1, 3-oxazine-2 or 3 or 4 or 5 or 6-yl; 5,6-dihydro-2H-1, 3-oxazine-2 or 4 or
5- oder 6-yl; 5.6-Dihydro-4H-1 ,3-oxazin-2- oder 4- oder 5- oder 6-yl; 2H-1 ,3-Oxazin-2- oder 4- oder 5- oder 6-yl; 6H-1 ,3-Oxazin-2- oder 4- oder 5- oder 6-yl; 4H-1 ,3-Oxazin-2- oder 4- oder 5- oder 6-yl; Morpholin-2- oder 3- oder 4-yl; 3,4-Dihydro-2H-1 ,4-oxazin-2- oder 3- oder 4- oder 5- oder 6-yl; 3,6-Dihydro-2H-1 ,4-oxazin-2- oder 3- oder 5- oder 6- yl; 2H-1 ,4-oxazin-2- oder 3- oder 5- oder 6-yl; 4H-1 ,4-oxazin-2- oder 3-yl; 1 .2- Oxazepan-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3,4.5-Tetrahydro-1 ,2- oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3,4,7-Tetrahydro-1 ,2-oxazepin- 2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3.6,7-Tetrahydro-1 ,2-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,5.6,7-Tetrahydro-1 ,2-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 4.5,6.7-Tetrahydro-1 ,2-oxazepin-3- oder 4- oder 5- oder 6- oder 7-yl; 2,3-Dihydro-1 ,2-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,5- Dihydro-1 ,2-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2.7-Dihydro-1 ,2- oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 4,5-Dihydro-1 ,2-oxazepin-3- oder5- or 6-yl; 5.6-dihydro-4H-1,3-oxazine-2- or 4- or 5- or 6-yl; 2H-1, 3-oxazine-2- or 4- or 5- or 6-yl; 6H-1, 3-oxazine-2 or 4 or 5 or 6-yl; 4H-1, 3-oxazine-2 or 4 or 5 or 6-yl; Morpholine-2- or 3- or 4-yl; 3,4-dihydro-2H-1,4-oxazine-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-1,4-oxazine-2 or 3 or 5 or 6-yl; 2H-1,4-oxazine-2- or 3- or 5- or 6-yl; 4H-1,4-oxazine-2 or 3-yl; 1, 2-oxazepan-2 or 3 or 4 or 5 or 6 or 7-yl; 2,3,4,5-tetrahydro-1,2,10-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,7-tetrahydro-1,2-oxazepine 2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,6,7-tetrahydro-1,2-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 2,5,6,7-tetrahydro-1,2-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 4,5,6,7-tetrahydro-1,2-oxazepine-3- or 4- or 5- or 6- or 7-yl; 2,3-dihydro-1,2-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 2,5-dihydro-1,2-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 2,7-dihydro-1, 2-oxazepine-2 or 3 or 4 or 5 or 6 or 7-yl; 4,5-dihydro-1,2-oxazepine-3 or
4- oder 5- oder 6- oder 7-yl; 4,7-Dihydro-1 ,2-oxazepin-3- oder 4- oder 5- oder 6- oder
7-yl; 6,7-Dihydro-1 ,2-oxazepin-3- oder 4- oder 5- oder 6- oder 7-yl; 1 ,2-Oxazepin-3- oder 4- oder 5- oder 6- oder 7-yl; 1 ,3-Oxazepan-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2.3.4.5-Tetrahydro-1 ,3-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2.3.4,7-Tetrahydro-1 ,3-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3,6.7- Tetrahydro-1 ,3-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,5,6.7-4- or 5- or 6- or 7-yl; 4,7-dihydro-1,2-oxazepine-3 or 4 or 5 or 6 or 7-yl; 6,7-dihydro-1,2-oxazepine-3- or 4- or 5- or 6- or 7-yl; 1,2-oxazepine-3- or 4- or 5- or 6- or 7-yl; 1,3-oxazepan-2- or 3- or 4- or 5- or 6- or 7-yl; 2.3.4.5-tetrahydro-1,3-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,7-tetrahydro-1,3-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,6,7-tetrahydro-1,3-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 2,5,6.7-
Tetrahydro-1 ,3-oxazepin-2- oder 4- oder 5- oder 6- oder 7-yl; 4,5,6.7-Tetrahydro-1 ,3- oxazepin-2- oder 4- oder 5- oder 6- oder 7-yl; 2.3-Dihydro-1 ,3-oxazepin-2- oder 3- oderTetrahydro-1,3-oxazepine-2- or 4- or 5- or 6- or 7-yl; 4,5,6,7-tetrahydro-1,3,10-oxazepine-2- or 4- or 5- or 6- or 7-yl; 2,3-dihydro-1,3-oxazepine-2- or 3- or
4- oder 5- oder 6- oder 7-yl; 2,5-Dihydro-1 ,3-oxazepin-2- oder 4- oder 5- oder 6- oder 7-yl; 2,7-Dihydro-1 ,3-oxazepin-2- oder 4- oder 5- oder 6- oder 7-yl; 4,5-Dihydro-1 .3- oxazepin-2- oder 4- oder 5- oder 6- oder 7-yl; 4,7-Dihydro-1 ,3-oxazepin-2- oder 4- oder4- or 5- or 6- or 7-yl; 2,5-dihydro-1,3-oxazepine-2- or 4- or 5- or 6- or 7-yl; 2,7-dihydro-1,3-oxazepine-2- or 4- or 5- or 6- or 7-yl; 4,5-dihydro-1,3-oxazepine-2- or 4- or 5- or 6- or 7-yl; 4,7-dihydro-1,3-oxazepine-2- or 4- or
5- oder 6- oder 7-yl; 6,7-Dihydro-1 ,3-oxazepin-2- oder 4- oder 5- oder 6- oder 7-yl; 1 ,3-Oxazepin-2- oder 4- oder 5- oder 6- oder 7-yl; 1 ,4-Oxazepan-2- oder 3- oder 5- oder 6- oder 7-yl; 2,3,4,5-Tetrahydro-1 ,4-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3,4.7-Tetrahydro-1 ,4-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3,6,7-Tetrahydro-1 ,4-oxazepin-2- oder 3- oder 5- oder 6- oder 7-yl; 2.5,6,7-5- or 6- or 7-yl; 6,7-dihydro-1,3-oxazepine-2- or 4- or 5- or 6- or 7-yl; 1,3-oxazepine-2- or 4- or 5- or 6- or 7-yl; 1,4-oxazepan-2- or 3- or 5- or 6- or 7-yl; 2,3,4,5-tetrahydro-1,4-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,7-tetrahydro-1,4-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,6,7-tetrahydro-1,4-oxazepine-2- or 3- or 5- or 6- or 7-yl; 2.5,6,7-
Tetrahydro-1 ,4-oxazepin-2- oder 3- oder 5- oder 6- oder 7-yl; 4.5,6.7-Tetrahydro-1 .4- oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3-Dihydro-1 ,4-oxazepin-2- oder 3- oder 5- oder 6- oder 7-yl; 2,5-Dihydro-1 ,4-oxazepin-2- oder 3- oder 5- oder 6- oder 7-yl; 2,7-Dihydro-1 ,4-oxazepin-2- oder 3- oder 5- oder 6- oder 7-yl; 4.5-Dihydro-1 ,4- oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 4,7-Dihydro-1 ,4-oxazepin-2- oderTetrahydro-1,4-oxazepine-2- or 3- or 5- or 6- or 7-yl; 4,5,6,7-tetrahydro-1, 4-oxazepine-2 or 3 or 4 or 5 or 6 or 7-yl; 2,3-dihydro-1,4-oxazepine-2- or 3- or 5- or 6- or 7-yl; 2,5-dihydro-1,4-oxazepine-2- or 3- or 5- or 6- or 7-yl; 2,7-dihydro-1,4-oxazepine-2- or 3- or 5- or 6- or 7-yl; 4,5-dihydro-1,4-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 4,7-Dihydro-1,4-oxazepine-2-Or
3- oder 4- oder 5- oder 6- oder 7-yl; 6.7-Dihydro-1 ,4-oxazepin-2- oder 3- oder 5- oder3- or 4- or 5- or 6- or 7-yl; 6,7-Dihydro-1,4-oxazepine-2- or 3- or 5- or
6- oder 7-yl; 1 ,4-Oxazepin-2- oder 3- oder 5- oder 6- oder 7-yl; lsothiazolidin-2- oder 3- oder 4- oder 5-yl; 2,3-Dihydroisothiazol-2- oder 3- oder 4- oder 5-yl; 2,5- Dihydroisothiazol-2- oder 3- oder 4- oder 5-yl; 4.5-Dihydroisothiazol-3- oder 4- oder 5- yl; 1 ,3-Thiazolidin-2- oder 3- oder 4- oder 5-yl; 2.3-Dihydro-1 ,3-thiazol-2- oder 3- oder6- or 7-yl; 1,4-oxazepine-2- or 3- or 5- or 6- or 7-yl; isothiazolidine-2- or 3- or 4- or 5-yl; 2,3-dihydroisothiazole-2- or 3- or 4- or 5-yl; 2,5-dihydroisothiazole-2 or 3 or 4 or 5-yl; 4,5-dihydroisothiazole-3 or 4 or 5-yl; 1,3-thiazolidine-2- or 3- or 4- or 5-yl; 2,3-dihydro-1, 3-thiazole-2 or 3 or
4- oder 5-yl; 2.5-Dihydro-1 ,3-thiazol-2- oder 4- oder 5-yl; 4,5-Dihydro-1 ,3-thiazol-2- oder 4- oder 5-yl; 1 ,3-Thiazinan-2- oder 3- oder 4- oder 5- oder 6-yl; 3,4-Dihydro-2H- 1 ,3-thiazin-2- oder 3- oder 4- oder 5- oder 6-yl; 3,6-Dihydro-2H-1 ,3-thiazin-2- oder 3- oder 4- oder 5- oder 6-yl; 5,6-Dihydro-2H-1 ,3-thiazin-2- oder 4- oder 5- oder 6-yl; 5,6- Dihydro-4H-1 ,3-thiazin-2- oder 4- oder 5- oder 6-yl; 2H-1 .3-Thiazin-2- oder 4- oder 5- oder 6-yl; 6H-1 ,3-Thiazin-2- oder 4- oder 5- oder 6-yl; 4H-1 ,3-Thiazin-2- oder 4- oder4- or 5-yl; 2,5-dihydro-1, 3-thiazole-2 or 4 or 5-yl; 4,5-dihydro-1,3-thiazole-2- or 4- or 5-yl; 1, 3-thiazinan-2 or 3 or 4 or 5 or 6-yl; 3,4-dihydro-2H-1, 3-thiazine-2 or 3 or 4 or 5 or 6-yl; 3,6-dihydro-2H-1, 3-thiazine-2 or 3 or 4 or 5 or 6-yl; 5,6-dihydro-2H-1, 3-thiazine-2 or 4 or 5 or 6-yl; 5,6-dihydro-4H-1, 3-thiazine-2 or 4 or 5 or 6-yl; 2H-1, 3-thiazine-2 or 4 or 5 or 6-yl; 6H-1, 3-thiazine-2 or 4 or 5 or 6-yl; 4H-1, 3-thiazine-2 or 4 or
5- oder 6-yl. Weitere Beispiele für "Heterocyclyl" sind ein partiell oder vollständig hydrierter heterocyclischer Rest mit 3 Heteroatomen aus der Gruppe N, O und S, wie beispielsweise 1 ,4,2-Dioxazolidin-2- oder 3- oder 5-yl; 1 ,4,2-Dioxazol-3- oder 5-yl;
1 ,4,2-Dioxazinan-2- oder -3- oder 5- oder 6-yl; 5,6-Dihydro-1 ,4,2-dioxazin-3- oder 5- oder 6-yl; 1 .4,2-Dioxazin-3- oder 5- oder 6-yl; 1 ,4?2-Dioxazepan-2- oder 3- oder 5- oder 6- oder 7-yl; 6,7-Dihydro-5H-1 ,4,2-Dioxazepin-3- oder 5- oder 6- oder 7-yl; 2.3- Dihydro-7H-1 A2-Dioxazepin-2- oder 3- oder 5- oder 6- oder 7-yl; 2,3-Dihydro-5H- 1 .4.2-Dioxazepin-2- oder 3- oder 5- oder 6- oder 7-yl; 5H-1 A2-Dioxazepin-3- oder 5- oder 6- oder 7-yl; 7H-1 ,4,2-Dioxazepin-3- oder 5- oder 6- oder 7-yl. Strukturbeispiele für gegebenenfalls weiter substituierte Heterocyclen sind auch im Folgenden aufgeführt: 5- or 6-yl. Further examples of "heterocyclyl" are a partially or fully hydrogenated heterocyclic radical having 3 heteroatoms from the group N, O and S, such as, for example, 1, 4,2-dioxazolidin-2 or 3 or 5-yl; 1, 4,2-dioxazol-3 or 5-yl; 1,2,2-dioxazinane-2- or -3- or 5- or 6-yl; 5,6-dihydro-1,2,2,2-dioxazine-3- or 5- or 6-yl; 1, 4,2-dioxazine-3- or 5- or 6-yl; 1, 4 ? 2-dioxazepan-2- or 3- or 5- or 6- or 7-yl; 6,7-dihydro-5H-1, 4,2-dioxazepine-3 or 5 or 6 or 7-yl; 2.3-dihydro-7H-1 A2-dioxazepine-2- or 3- or 5- or 6- or 7-yl; 2,3-dihydro-5H-1, 4,2-dioxazepin-2 or 3 or 5 or 6 or 7-yl; 5H-1 A2-dioxazepin-3 or 5 or 6 or 7-yl; 7H-1, 4,2-dioxazepine-3 or 5 or 6 or 7-yl. Structural examples of optionally further substituted heterocycles are also listed below:
Die oben aufgeführten Heterocyclen sind bevorzugt beispielsweise durch Wasserstoff, Halogen, Alkyl, Haloalkyl, Hydroxy, Alkoxy, Cycloalkoxy, Aryloxy, Alkoxyalkyl, The heterocycles listed above are preferably, for example, hydrogen, halogen, alkyl, haloalkyl, hydroxy, alkoxy, cycloalkoxy, aryloxy, alkoxyalkyl,
Alkoxyalkoxy, Cycloalkyl, Halocycloalkyl, Aryl, Arylalkyl, Heteroaryl, Heterocyclyl, Alkenyl, Alkylcarbonyl, Cycloalkylcarbonyl, Arylcarbonyl, Heteroarylcarbonyl, Alkoxyalkoxy, cycloalkyl, halocycloalkyl, aryl, arylalkyl, heteroaryl, heterocyclyl, alkenyl, alkylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl,
Alkoxy carbonyl, Hydroxycarbonyl, Cycloalkoxycarbonyl, Cycloalkylalkoxycarbonyl, Alkoxy carbonylalkyl, Arylalkoxycarbonyl, Arylalkoxycarbonylalkyl, Alkinyl, Alkinylalkyl, Alkylalkinyl, Tris-alkylsilylalkinyl, Nitro, Amino, Cyano, Haloalkoxy, Haloalkylthio, Alkylthio, Hydrothio, Hydroxyalkyl, Oxo, Heteroarylalkoxy, Arylalkoxy, Alkoxycarbonyl, hydroxycarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, alkoxycarbonylalkyl, arylalkoxycarbonyl, arylalkoxycarbonylalkyl, alkynyl, alkynylalkyl, alkylalkynyl, trisalkylsilylalkynyl, nitro, amino, cyano, haloalkoxy, haloalkylthio, alkylthio, hydrothio, hydroxyalkyl, oxo, heteroarylalkoxy, arylalkoxy,
Heterocyclylalkoxy, Heterocyclylalkylthio, Heterocyclyloxy, Heterocyclylthio, Heterocyclylalkoxy, heterocyclylalkylthio, heterocyclyloxy, heterocyclylthio,
Heteroaryloxy, Bis-alkylamino, Alkylamino, Cycloalkylamino, Heteroaryloxy, bis-alkylamino, alkylamino, cycloalkylamino,
Hydroxycarbonylalkylamino, Alkoxycarbonylalkylamino, Arylalkoxycarbonylalkylamino, Alkoxycarbonylalkyl(alkyl)amino, Aminocarbonyl, Alkylaminocarbonyl, Bis- alkylaminocarbonyl, Cycloalkylaminocarbonyl, Hydroxycarbonylalkylaminocarbonyl, Alkoxy carbonylalkylaminocarbonyl, Arylalkoxy carbonylalkylaminocarbonyl substituiert. Hydroxycarbonylalkylamino, alkoxycarbonylalkylamino, arylalkoxycarbonylalkylamino, alkoxycarbonylalkyl (alkyl) amino, aminocarbonyl, alkylaminocarbonyl, bis-alkylaminocarbonyl, cycloalkylaminocarbonyl, hydroxycarbonylalkylaminocarbonyl, alkoxycarbonylalkylaminocarbonyl, arylalkoxycarbonylalkylaminocarbonyl.
Wenn ein Grundkörper "durch einen oder mehrere Reste" aus einer Aufzählung von Resten (= Gruppe) oder einer generisch definierten Gruppe von Resten substituiert ist, so schließt dies jeweils die gleichzeitige Substitution durch mehrere gleiche und/oder strukturell unterschiedliche Reste ein. If a main body is "substituted by one or more radicals" from an enumeration of radicals (= group) or a generically defined group of radicals, this includes the simultaneous substitution by a plurality of identical and / or structurally different radicals.
Handelt es sich es sich um einen teilweise oder vollständig gesättigten Stickstoff- Heterocyclus, so kann dieser sowohl über Kohlenstoff als auch über den Stickstoff mit dem Rest des Moleküls verknüpft sein.
Als Substituenten für einen substituierten heterocyclischen Rest kommen die weiter unten genannten Substituenten in Frage, zusätzlich auch Oxo und Thioxo. Die If it is a partially or fully saturated nitrogen heterocycle, it may be linked to the rest of the molecule via both carbon and nitrogen. Suitable substituents for a substituted heterocyclic radical are the substituents mentioned below, in addition to oxo and thioxo. The
Oxogruppe als Substituent an einem Ring-C-Atom bedeutet dann beispielsweise eine Carbonylgruppe im heterocyclischen Ring. Dadurch sind vorzugsweise auch Lactone und Lactame umfasst. Die Oxogruppe kann auch an den Heteroringatomen, die in verschiedenen Oxidationsstufen existieren können, z.B. bei N und S, auftreten und bilden dann beispielsweise die divalenten Gruppen N(O) , S(O) (auch kurz SO) und S(0)2 (auch kurz S02) im heterocyclischen Ring. Im Fall von -N(O)- und -S(O)- Gruppen sind jeweils beide Enantiomere umfasst. Oxo group as a substituent on a ring C atom then means, for example, a carbonyl group in the heterocyclic ring. As a result, lactones and lactams are preferably also included. The oxo group may also be attached to the hetero ring atoms, which may exist in different oxidation states, e.g. in the case of N and S, for example, the divalent groups N (O), S (O) (also known as SO) and S (O) 2 (also abbreviated to SO 2) occur and form in the heterocyclic ring. In the case of -N (O) and -S (O) groups, both enantiomers are included.
Erfindungsgemäß steht der Ausdruck„Heteroaryl" für heteroaromatische According to the invention, the term "heteroaryl" is heteroaromatic
Verbindungen, d. h. vollständig ungesättigte aromatische heterocyclische Compounds, d. H. fully unsaturated aromatic heterocyclic
Verbindungen, vorzugsweise für 5- bis 7-gliedrige Ringe mit 1 bis 4, vorzugsweise 1 oder 2 gleichen oder verschiedenen Heteroatomen, vorzugsweise O, S oder N. Compounds, preferably for 5- to 7-membered rings having 1 to 4, preferably 1 or 2 identical or different heteroatoms, preferably O, S or N.
Erfindungsgemäße Heteroaryle sind beispielsweise 1 H-Pyrrol-1 -yl; 1 H-Pyrrol-2-yl; 1 H- Pyrrol-3-yl; Furan-2-yl; Furan-3-yl; Thien-2-yl; Thien-3-yl, 1 H-lmidazol-1 -yl; 1 H- lmidazol-2-yl; 1 H-lmidazol-4-yl; 1 H-lmidazol-5-yl; 1 H-Pyrazol-1 -yl; 1 H-Pyrazol-3-yl; 1 H- Pyrazol-4-yl; 1 H-Pyrazol-5-yl, 1 H-1 ,2,3-Triazol-1 -yl, 1 H-1 ,2.3-Triazol-4-yl, 1 H-1 .2,3- Triazol-5-yl, 2H-1 ,2,3-Triazol-2-yl, 2H-1 ,2,3-Triazol-4-yl, 1 H-1 ,2,4-Triazol-1 -yl, 1 H- 1 ,2,4-Triazol-3-yl, 4H-1 ,2,4-Triazol-4-yl, 1 ,2.4-Oxadiazol-3-yl, 1 .2,4-Oxadiazol-5-yl, 1 ,3,4-Oxadiazol-2-yl, 1 ,2.3-Oxadiazol-4-yl, 1 ,2.3-Oxadiazol-5-yl, 1 ,2.5-Oxadiazol-3-yl, Azepinyl, Pyridin-2-yl, Pyridin-3-yl, Pyridin-4-yl, Pyrazin-2-yl, Pyrazin-3-yl, Pyrimidin-2- yl, Pyrimidin-4-yl, Pyrimidin-5-yl, Pyridazin-3-yl, Pyridazin-4-yl, 1 ,3,5-Triazin-2-yl, 1 ,2,4- Triazin-3-yl, 1 ,2,4-Triazin-5-yl, 1 ,2,4-Triazin-6-yl, 1 .2,3-Triazin-4-yl, 1 ,2.3-Triazin-5-yl, 1 .2,4-, 1 ,3.2-, 1 ,3.6- und 1 ,2,6-Oxazinyl, lsoxazol-3-yl, lsoxazol-4-yl, lsoxazol-5-yl, 1 .3- Oxazol-2-yl, 1 ,3-Oxazol-4-yl, 1 ,3-Oxazol-5-yl, lsothiazol-3-yl, lsothiazol-4-yl, Isothiazol- 5-yl, 1 .3-Thiazol-2-yl, 1 ,3-Thiazol-4-yl, 1 .3-Thiazol-5-yl, Oxepinyl, Thiepinyl, 1 ,2.4- Triazolonyl und 1 ,2.4-Diazepinyl, 2H-1 .2,3.4-Tetrazol-5-yl, 1 H-1 ,2,3.4-Tetrazol-5-yl, 1 ,2,3,4-Oxatriazol-5-yl, 1 ,2,3,4-Thiatriazol-5-yl, 1 ,2,3.5-Oxatriazol-4-yl, 1 ,2.3.5- Heteroaryls of the invention are, for example, 1H-pyrrol-1-yl; 1H-pyrrol-2-yl; 1H-pyrrol-3-yl; Furan-2-yl; Furan-3-yl; Thien-2-yl; Thien-3-yl, 1H-imidazole-1-yl; 1 H-imidazol-2-yl; 1 H -imidazol-4-yl; 1 H -imidazol-5-yl; 1H-pyrazole-1-yl; 1H-pyrazol-3-yl; 1H-pyrazol-4-yl; 1 H-pyrazol-5-yl, 1 H-1, 2,3-triazol-1-yl, 1 H-1, 2,3-triazol-4-yl, 1 H-1, 2, 3-triazole-5 yl, 2H-1, 2,3-triazol-2-yl, 2H-1, 2,3-triazol-4-yl, 1H-1, 2,4-triazol-1-yl, 1H-1, 2,4-triazol-3-yl, 4H-1, 2,4-triazol-4-yl, 1, 2,4-oxadiazol-3-yl, 1, 2, 4-oxadiazol-5-yl, 1, 3, 4-oxadiazol-2-yl, 1, 2.3-oxadiazol-4-yl, 1, 2.3-oxadiazol-5-yl, 1, 2.5-oxadiazol-3-yl, azepinyl, pyridin-2-yl, pyridine-3 yl, pyridin-4-yl, pyrazine-2-yl, pyrazine-3-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyridazin-3-yl, pyridazin-4-yl, 1, 3,5-triazin-2-yl, 1, 2,4-triazin-3-yl, 1, 2,4-triazin-5-yl, 1, 2,4-triazin-6-yl, 1. 2,3-triazin-4-yl, 1, 2,3-triazin-5-yl, 1, 2, 4, 1, 3.2, 1, 3.6 and 1, 2,6-oxazinyl, isoxazol-3-yl , isoxazol-4-yl, isoxazol-5-yl, 1, 3-oxazol-2-yl, 1, 3-oxazol-4-yl, 1, 3-oxazol-5-yl, isothiazol-3-yl, isothiazole 4-yl, isothiazol-5-yl, 1, 3-thiazol-2-yl, 1, 3-thiazol-4-yl, 1, 3-thiazol-5-yl, oxepinyl, thiepinyl, 1, 2,4-triazolonyl and 1, 2,4-diazepinyl, 2H-1,2,3,4-tetrazol-5-yl, 1H-1, 2 , 3,4-Tetrazol-5-yl, 1, 2,3,4-oxatriazol-5-yl, 1, 2,3,4-thiatriazol-5-yl, 1, 2,3,5-oxatriazol-4-yl, 1 , 2.3.5-
Thiatriazol-4-yl. Die erfindungsgemäßen Heteroarylgruppen können ferner mit einem oder mehreren, gleichen oder verschiedenen Resten substituiert sein. Sind zwei benachbarte Kohlenstoffatome Bestandteil eines weiteren aromatischen Rings, so handelt es sich um annellierte heteroaromatische Systeme, wie benzokondensierte
oder mehrfach anneliierte Heteroaromaten. Bevorzugt sind beispielsweise Chinoline (z. B. Chinolin-2-yl, Chinolin-3-yl, Chinolin-4-yl, Chinolin-5-yl, Chinolin-6-yl, Chinolin-7- yl, Chinolin-8-yl); Isochinoline (z. B. lsochinolin-1 -yl, lsochinolin-3-yl, lsochinolin-4-yl, lsochinolin-5-yl, lsochinolin-6-yl, lsochinolin-7-yl, lsochinolin-8-yl); Chinoxalin; Thiatriazole-4-yl. The heteroaryl groups according to the invention may furthermore be substituted by one or more identical or different radicals. If two adjacent carbon atoms are part of another aromatic ring, they are fused heteroaromatic systems, such as benzo-fused or multiply annelated heteroaromatics. Preference is given, for example, to quinolines (for example quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl ); Isoquinolines (e.g., isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl, isoquinolin-8-yl); quinoxaline;
Chinazolin; Cinnolin; 1 ,5-Naphthyridin; 1 ,6-Naphthyridin; 1 ,7-Naphthyridin; 1 ,8- Naphthyridin; 2.6-Naphthyridin; 2,7-Naphthyridin; Phthalazin; Pyridopyrazine; quinazoline; cinnoline; 1,5-naphthyridine; 1,6-naphthyridine; 1,7-naphthyridine; 1,8-naphthyridine; 2,6-naphthyridine; 2,7-naphthyridine; phthalazine; Pyridopyrazine;
Pyridopyrimidine; Pyridopyridazine; Pteridine; Pyrimidopyrimidine. Beispiele für Heteroaryl sind auch 5- oder 6-gliedrige benzokondensierte Ringe aus der Gruppe 1 H- lndol-1 -yl, 1 H-lndol-2-yl, 1 H-lndol-3-yl, 1 H-lndol-4-yl, 1 H-lndol-5-yl, 1 H-lndol-6-yl, 1 H- lndol-7-yl, 1 -Benzofuran-2-yl, 1 -Benzofuran-3-yl, 1 -Benzofuran-4-yl, 1-Benzofuran-5-yl, 1 -Benzofuran-6-yl, 1 -Benzofuran-7-yl, 1 -Benzothiophen-2-yl, 1 -Benzothiophen-3-yl, 1 - Benzothiophen-4-yl, 1 -Benzothiophen-5-yl, 1 -Benzothiophen-6-yl, 1 -Benzothiophen-7- yl, 1 H-lndazol-1 -yl, 1 H-lndazol-3-yl, 1 H-lndazol-4-yl, 1 H-lndazol-5-yl. 1 H-lndazol-6-yl, 1 H-lndazol-7-yl, 2H-lndazol-2-yl, 2H-lndazol-3-yl, 2H-lndazol-4-yl, 2H-lndazol-5-yl, 2H- lndazol-6-yl, 2H-lndazol-7-yl, 2H-lsoindol-2-yl, 2H-lsoindol-1 -yl, 2H-lsoindol-3-yl, 2H- lsoindol-4-yl, 2H-lsoindol-5-yl, 2H-lsoindol-6-yl; 2H-lsoindol-7-yl, 1 H-Benzimidazol-1 -yl, 1 H-Benzimidazol-2-yl, 1 H-Benzimidazol-4-yl, 1 H-Benzimidazol-5-yl, 1 H-Benzimidazol- 6-yl, 1 H-Benzimidazol-7-yl, 1 ,3-Benzoxazol-2-yl, 1 .3-Benzoxazol-4-yl, 1 ,3-Benzoxazol- 5-yl, 1 ,3-Benzoxazol-6-yl, 1 ,3-Benzoxazol-7-yl, 1 ,3-Benzthiazol-2-yl, 1 ,3-Benzthiazol-4- yl, 1 .3-Benzthiazol-5-yl. 1 ,3-Benzthiazol-6-yl, 1 .3-Benzthiazol-7-yl, 1 ,2-Benzisoxazol-3- yl, 1 ,2-Benzisoxazol-4-yl, 1 ,2-Benzisoxazol-5-yl, 1 ,2-Benzisoxazol-6-yl, 1 .2- Benzisoxazol-7-yl, 1 ,2-Benzisothiazol-3-yl, 1 ,2-Benzisothiazol-4-yl, 1 ,2-Benzisothiazol- 5-yl, 1 ,2-Benzisothiazol-6-yl, 1 ,2-Benzisothiazol-7-yl. Die Bezeichnung "Halogen" bedeutet beispielsweise Fluor, Chlor, Brom oder lod. Wird die Bezeichnung für einen Rest verwendet, dann bedeutet "Halogen" beispielsweise ein Fluor-, Chlor-, Brom- oder lodatom. pyridopyrimidines; Pyridopyridazine; pteridines; Pyrimidopyrimidine. Examples of heteroaryl are also 5- or 6-membered benzo-fused rings from the group 1H-indol-1-yl, 1H-indol-2-yl, 1H-indol-3-yl, 1H-indole-4 yl, 1H-indol-5-yl, 1H-indol-6-yl, 1H-indol-7-yl, 1-benzofuran-2-yl, 1-benzofuran-3-yl, 1-benzofuran-4 -yl, 1-benzofuran-5-yl, 1-benzofuran-6-yl, 1-benzofuran-7-yl, 1-benzothiophen-2-yl, 1-benzothiophen-3-yl, 1-benzothiophen-4-yl , 1-benzothiophene-5-yl, 1-benzothiophene-6-yl, 1-benzothiophene-7-yl, 1-indazol-1-yl, 1-indazol-3-yl, 1-indazole-4-yl yl, 1H-indazol-5-yl. 1 H-indazol-6-yl, 1 H-indazol-7-yl, 2H-indazol-2-yl, 2H-indazol-3-yl, 2H-indazol-4-yl, 2H-indazol-5-yl, 2H-indazol-6-yl, 2H-indazol-7-yl, 2H-isoindol-2-yl, 2H-isoindol-1-yl, 2H-isoindol-3-yl, 2H-isoindol-4-yl, 2H- isoindol-5-yl, 2H-isoindol-6-yl; 2H-isoindol-7-yl, 1H-benzimidazol-1-yl, 1H-benzimidazol-2-yl, 1H-benzimidazol-4-yl, 1H-benzimidazol-5-yl, 1H-benzimidazole-6 -yl, 1H-benzimidazol-7-yl, 1, 3-benzoxazol-2-yl, 1, 3-benzoxazol-4-yl, 1, 3-benzoxazol-5-yl, 1, 3-benzoxazole-6 yl, 1,3-benzoxazol-7-yl, 1,3-benzthiazol-2-yl, 1,3-benzthiazol-4-yl, 1, 3-benzthiazol-5-yl. 1, 3-benzthiazol-6-yl, 1, 3-benzthiazol-7-yl, 1, 2-benzisoxazol-3-yl, 1, 2-benzisoxazol-4-yl, 1, 2-benzisoxazol-5-yl, 1, 2-benzisoxazol-6-yl, 1, 2-benzisoxazol-7-yl, 1, 2-benzisothiazol-3-yl, 1, 2-benzisothiazol-4-yl, 1, 2-benzisothiazol-5-yl, 1,2-benzisothiazol-6-yl, 1,2-benzisothiazol-7-yl. The term "halogen" means, for example, fluorine, chlorine, bromine or iodine. When the term for a group is used, "halogen" means, for example, a fluorine, chlorine, bromine or iodine atom.
Erfindungsgemäß bedeutet„Alky!" einen geradkettigen oder verzweigten offenkettigen, gesättigten Kohlenwasserstoffrest, der gegebenenfalls ein- oder mehrfach substituiert ist. Bevorzugte Substituenten sind Halogenatome, Alkoxy-, Haloalkoxy-, Cyano-, Alkylthio, Haloalkylthio-, Amino- oder Nitrogruppen, besonders bevorzugt sind According to the invention, "alky!" Denotes a straight-chain or branched, open-chain, saturated hydrocarbon radical which is optionally monosubstituted or polysubstituted Preferred substituents are halogen atoms, alkoxy, haloalkoxy, cyano, alkylthio, haloalkylthio, amino or nitro groups, more preferably are
Methoxy, Methyl, Fluoralkyl, Cyano, Nitro, Fluor, Chlor, Brom oder lod.
„Haloalkyl", ,,-alkenyl" und ,,-alkinyl" bedeuten durch gleiche oder verschiedene Methoxy, methyl, fluoroalkyl, cyano, nitro, fluoro, chloro, bromo or iodo. "Haloalkyl", "- alkenyl" and "alkynyl" mean the same or different
Halogenatome, teilweise oder vollständig substituiertes Alkyl, Alkenyl bzw. Alkinyl, z.B. Monohaloalkyl (= Monohalogenalkyl) wie z. B. CH2CH2CI, CH2CH2Br, CHCICH3, CH2CI, CH2F; Perhaloalkyl wie z. B. CCI3. CCIF2, CFCI2,CF2CCIF2, CF2CCIFCF3; Halogen atoms, partially or fully substituted alkyl, alkenyl or alkynyl, for example monohaloalkyl (= monohaloalkyl) such. CH 2 CH 2 Cl, CH 2 CH 2 Br, CHCICH 3 , CH 2 Cl, CH 2 F; Perhaloalkyl such. B. CCI 3 . CCIF 2 , CFCI 2 , CF 2 CCIF 2 , CF2CCIFCF3;
Polyhaloalkyl wie z. B. CH2CHFCI, CF2CCIFH, CF2CBrFH, CH2CF3; Der Begriff Perhaloalkyl umfasst dabei auch den Begriff Perfluoralkyl. Polyhaloalkyl such. CH 2 CHFCI, CF 2 CCIFH, CF 2 CBrFH, CH 2 CF 3 ; The term perhaloalkyl also encompasses the term perfluoroalkyl.
Teilfluoriertes Alkyl bedeutet einen geradkettigen oder verzweigten, gesättigten Partially fluorinated alkyl means a straight-chain or branched, saturated
Kohlenwasserstoff, der einfach oder mehrfach durch Fluor substituiert ist, wobei sich die entsprechenden Fluoratome als Substituenten an einem oder mehreren Hydrocarbon which is mono- or polysubstituted by fluorine, wherein the corresponding fluorine atoms as substituents on one or more
verschiedenen Kohlenstoffatomen der geradkettigen oder verzweigten different carbon atoms of the straight-chain or branched
Kohlenwasserstoffkette befinden können, wie z. B. CHFCH3, CH2CH2F, CH2CH2CF3, CHF2, CH2F, CHFCF2CF3 Teilfluoriertes Haloalkyl bedeutet einen geradkettigen oder verzweigten, gesättigten Kohlenwasserstoff, der durch verschiedenene Halogenatomen mit mindestens einem Fluoratom substituiert ist, wobei alle anderen gegebenenfalls vorhandenen Hydrocarbon chain can be located, such as. B. CHFCH3, CH 2 CH 2 F, CH 2 CH 2 CF 3, CHF 2, CH 2 F, CHFCF 2 CF 3 partially fluorinated haloalkyl is a straight or branched, saturated hydrocarbon which is substituted with at least one fluorine atom by verschiedenene halogen atoms, all others possibly present
Halogenatome ausgewählt sind aus der Gruppe Fluor, Chlor oder Brom, lod. Die entsprechenden Halogenatome können sich dabei als Substituenten an einem oder mehreren verschiedenen Kohlenstoffatomen der geradkettigen oder verzweigten Kohlenwasserstoffkette befinden. Teilfluoriertes Haloalkyl schließt auch die Halogen atoms are selected from the group fluorine, chlorine or bromine, iodine. The corresponding halogen atoms may be present as substituents on one or more different carbon atoms of the straight-chain or branched hydrocarbon chain. Partially fluorinated haloalkyl also includes the
vollständige Substitution der geradkettigen oder verzweigten Kette durch Halogen unter Beteiligung von mindestens einem Fluoratom ein. Haloalkoxy ist z.B. OCF3, OCHF2, OCH2F, OCF2CF3, OCH2CF3 und OCH2CH2CI; complete substitution of the straight-chain or branched chain by halogen with the participation of at least one fluorine atom. Haloalkoxy is, for example, OCF 3 , OCHF 2 , OCH 2 F, OCF 2 CF 3 , OCH 2 CF 3 and OCH 2 CH 2 Cl;
Entsprechendes gilt für Haloalkenyl und andere durch Halogen substituierten Reste. The same applies to haloalkenyl and other halogen-substituted radicals.
Der hier beispielhaft genannte Ausdruck "(C1-C4)- Alkyl" bedeutet eine The term "(C 1 -C 4) -alkyl" exemplified herein means a
Kurzschreibweise für geradkettiges oder verzweigtes Alkyl mit einem bis 4 Short notation for straight-chain or branched alkyl having one to four
Kohlenstoffatomen entsprechend der Bereichsangabe für C-Atome, d. h. umfasst die Reste Methyl, Ethyl, 1 -Propyl, 2-Propyl, 1 -Butyl, 2-Butyl, 2-Methylpropyl oder tert-Butyl. Allgemeine Alkylreste mit einem größeren angegebenen Bereich von C-Atomen, z. B. "(Ci-Ce)- Alkyl", umfassen entsprechend auch geradkettige oder verzweigte Alkylreste
mit einer größeren Zahl von C-Atomen, d. h. gemäß Beispiel auch die Alkylreste mit 5 und 6 C-Atomen. Carbon atoms corresponding to the range for C atoms, ie, the radicals include methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl. General alkyl radicals having a larger specified range of carbon atoms, eg. As "(Ci-Ce) - alkyl", accordingly also include straight-chain or branched alkyl radicals with a larger number of carbon atoms, ie according to the example also the alkyl radicals with 5 and 6 carbon atoms.
Wenn nicht speziell angegeben, sind bei den K o h I e n wa sse rstoff reste n wie Alkyl-, Alkenyl- und Alkinylresten, auch in zusammengesetzten Resten, die niederen Unless specifically stated, in the case of the compounds there are hydrogen radicals such as alkyl, alkenyl and alkynyl radicals, also in assembled radicals, the lower ones
Kohlenstoffgerüste, z.B. mit 1 bis 6 C-Atomen bzw. bei ungesättigten Gruppen mit 2 bis 6 C-Atomen, bevorzugt. Alkylreste, auch in den zusammengesetzten Resten wie Alkoxy, Haloalkyl usw., bedeuten z.B. Methyl, Ethyl, n- oder i-Propyl, n-, i-, t- oder 2-Butyl, Pentyle, Hexyle, wie n-Hexyl, i-Hexyl und 1 ,3-Dimethylbutyl, Heptyle, wie n-Heptyl, 1-Methylhexyl und 1 ,4-Dimethylpentyl; Alkenyl- und AI kinyl reste haben die Bedeutung der den Aikyiresten entsprechenden möglichen ungesättigten Reste, wobei mindestens eine Doppelbindung bzw. Dreifachbindung enthalten ist. Bevorzugt sind Reste mit einer Doppelbindung bzw. Dreifachbindung. Der Begriff„Alkenyl" schließt insbesondere auch geradkettige oder verzweigte offenkettige Kohlenwasserstoffreste mit mehr als einer Doppelbindung ein, wie 1 ,3- Butadienyl und 1 ,4-Pentadienyl, aber auch Allenyl- oder Kumulenyl-reste mit einer bzw. mehreren kumulierten Doppelbindungen, wie beispielsweise Allenyl (1 ,2- Propadienyl), 1 ,2-Butadienyl und 1 ,2,3-Pentatrienyl. Alkenyl bedeutet z.B. Vinyl, welches ggf. durch weitere Alkylreste substituiert sein kann, z.B. Pro p-1 -en-1 -yl, But-1 - en-1 -yl, Allyl, 1-Methyl-prop-2-en-1 -yl, 2-Methyl-prop-2-en-1 -yl, But-2-en-1-yl, 1 - Methyl-but-3-en-1-yl und 1 -Methyl-but-2-en-1 -yl, 2-Methyl-prop-1 -en-1 -yl, Carbon skeletons, e.g. with 1 to 6 C atoms or with unsaturated groups having 2 to 6 C atoms, preferred. Alkyl radicals, also in the assembled radicals such as alkoxy, haloalkyl, etc., mean e.g. Methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, i-hexyl and 1,3-dimethylbutyl, heptyls, such as n-heptyl, 1-methylhexyl and 1, 4-dimethylpentyl; Alkenyl and Al kinyl radicals have the meaning of the Aikyiresten corresponding possible unsaturated radicals, wherein at least one double bond or triple bond is included. Preference is given to radicals having a double bond or triple bond. The term "alkenyl" in particular also includes straight-chain or branched open-chain hydrocarbon radicals having more than one double bond, such as 1,3-butadienyl and 1,4-pentadienyl, but also allenyl or cumulenyl radicals having one or more cumulated double bonds, such as For example, allenyl (1,2-propadienyl), 1,2-butadienyl and 1,2,3-pentatrienyl.Alkenyl is, for example, vinyl, which may optionally be substituted by further alkyl radicals, eg Pro p-1 -ene-1-yl , But-1 - en-1 -yl, allyl, 1-methyl-prop-2-en-1-yl, 2-methyl-prop-2-en-1-yl, but-2-en-1-yl , 1-methylbut-3-en-1-yl and 1-methylbut-2-en-1-yl, 2-methyl-prop-1 -ene-1-yl,
1 -Methylprop-1 -en-1 -yl, 1 -Methylprop-2-en-1 -yl, 2-Methyl-prop-2-en-1 -yl, But-2-en-1 -yl, But-3-en-1 -yl, 1-Methyl-but-3-en-1 -yl oder 1 -Methyl-but-2-en-1 -yl, Pentenyl, 1-methylprop-1 -en-1-yl, 1-methylprop-2-en-1-yl, 2-methyl-prop-2-en-1-yl, but-2-en-1-yl, butyrene 3-en-1-yl, 1-methyl-but-3-en-1-yl or 1-methyl-but-2-en-1-yl, pentenyl,
2-Methylpentenyl oder Hexenyl. 2-methylpentenyl or hexenyl.
Der Begriff„Alkinyl" schließt insbesondere auch geradkettige oder verzweigte offenkettige Kohlenwasserstoffreste mit mehr als einer Dreifachbindung oder auch mit einer oder mehreren Dreifachbindungen und einer oder mehreren Doppelbindungen ein, wie beispielsweise 1 ,3-Butatrienyl bzw. 3-Penten-1 -in-1 -yl. (C2-Ce)- Alkinyl bedeutet beispielsweise Ethinyl, Propargyl, 1 -Methyl-prop-2-in-1 -yl, 2-Butinyl, The term "alkynyl" in particular also includes straight-chain or branched open-chain hydrocarbon radicals having more than one triple bond or else having one or more triple bonds and one or more double bonds, for example 1,3-butatrienyl or 3-penten-1-yn-1 -yl. (C 2 -C 6) -alkynyl is, for example, ethynyl, propargyl, 1-methylprop-2-yn-1-yl, 2-butynyl,
2-Pentinyl oder 2-Hexinyl, vorzugsweise Propargyl, But-2-in-1 -yl, But-3-in-1 -yl oder 1 -Methyl-but-3-in-1 -yl.
Der Begriff„Cycloalkyl" bedeutet ein carbocyclisches, gesättigtes Ringsystem mit vorzugsweise 3-8 Ring-C-Atomen, z.B. Cyclopropyl, Cyclobutyl, Cyclopentyl oder Cyclohexyl. Im Falle von gegebenenfalls substituiertem Cycloalkyl werden cyclische Systeme mit Substituenten umfasst, wobei auch Substituenten mit einer 2-pentynyl or 2-hexynyl, preferably propargyl, but-2-yn-1-yl, but-3-yn-1-yl or 1-methylbut-3-yn-1-yl. The term "cycloalkyl" means a carbocyclic saturated ring system preferably having 3-8 ring C atoms, eg, cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl In the case of optionally substituted cycloalkyl, cyclic systems having substituents are included, with substituents also having a
Doppelbindung am Cycloalkylrest, z. B. eine Alkylidengruppe wie Methyliden, umfasst sind. Im Falle von gegebenenfalls substituiertem Cycloalkyl werden auch Double bond on the cycloalkyl, z. As an alkylidene group such as methylidene, are included. In the case of optionally substituted cycloalkyl also become
mehrcyclische aliphatische Systeme umfaßt, wie beispielsweise Bicyclo[1 .1 .0]butan-1 - yl, Bicyclo[1 .1 .0]butan-2-yl, Bicyclo[2.1 .0]pentan-1 -yl, Bicyclo[2.1 .0]pentan-2-yl, Bicyclo[2.1 .0]pentan-5-yl, Bicyclo[2.2.1 ]hept-2-yl (Norbornyl), Bicyclo[2.2.2]octan-2-yl, Adamantan-1 -yl und Adamantan-2-yl. Der Ausdruck "(C3-C7)-Cycloalkyl" bedeutet eine Kurzschreibweise für Cycloalkyl mit drei bis 7 Kohlenstoffatomen entsprechend der Bereichsangabe für C-Atome. polycyclic aliphatic systems such as, for example, bicyclo [1, 1] -butan-1-yl, bicyclo [1, 1] -butan-2-yl, bicyclo [2.1.0] pentan-1-yl, bicyclo [2.1 .0] pentan-2-yl, bicyclo [2.1.0] pentan-5-yl, bicyclo [2.2.1] hept-2-yl (norbornyl), bicyclo [2.2.2] octan-2-yl, adamantane 1 -yl and adamantan-2-yl. The term "(C3-C7) cycloalkyl" means a shorthand notation for cycloalkyl having from three to seven carbon atoms corresponding to the range of C atoms.
Im Falle von substituiertem Cycloalkyl werden auch spirocyclische aliphatische Systeme umfaßt, wie beispielsweise Spiro[2.2]pent-1 -yl, Spiro[2.3]hex-1 -yl, In the case of substituted cycloalkyl, spirocyclic aliphatic systems are also included, such as spiro [2.2] pent-1-yl, spiro [2.3] hex-1-yl,
Spiro[2.3]hex-4-yl, 3-Spiro[2.3]hex-5-yl. Spiro [2.3] hex-4-yl, 3-spiro [2.3] hex-5-yl.
„Cycloalkenyl" bedeutet ein carbocyclisches, nicht aromatisches, partiell ungesättigtes Ringsystem mit vorzugsweise 4-8 C-Atomen, z.B. 1 -Cyclobutenyl, 2-Cyclobutenyl, 1- Cyclopentenyl, 2-Cyclopentenyl, 3-Cyclopentenyl, oder 1 -Cyclohexenyl, 2-"Cycloalkenyl" means a carbocyclic, non-aromatic, partially unsaturated ring system preferably having 4-8 C atoms, for example 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, or 1-cyclohexenyl, 2-
Cyclohexenyl, 3-Cyclohexenyl, 1 ,3-Cyclohexadienyl oder 1 .4-Cyclohexadienyl, wobei auch Substituenten mit einer Doppelbindung am Cycloalkenylrest, z. B. eine Cyclohexenyl, 3-cyclohexenyl, 1, 3-cyclohexadienyl or 1 .4-cyclohexadienyl, wherein also substituents having a double bond on the cycloalkenyl radical, z. Legs
Alkylidengruppe wie Methyliden, umfasst sind. Im Falle von gegebenenfalls substituiertem Cycloalkenyl gelten die Erläuterungen für substituiertes Cycloalkyl entsprechend. Alkylidene group such as methylidene, are included. In the case of optionally substituted cycloalkenyl, the explanations for substituted cycloalkyl apply correspondingly.
Der Begriff„Aikyliden", z. B. auch in der Form (Ci-Cio)-Alkyliden, bedeutet den Rest eines geradkettigen oder verzweigten offenkettigen Kohlenwasserstoffrests, der über eine Zweifachbindung gebunden ist. Als Bindungsstelle für Aikyliden kommen naturgemäß nur Positionen am Grundkörper in Frage, an denen zwei H-Atome durch die Doppelbindung ersetzt werden können; Reste sind z. B.
=CH-CH3, The term "acylidene", for example also in the form (C 1 -C 10) -alkylidene, means the radical of a straight-chain or branched open-chain hydrocarbon radical which is bonded via a double bond.As a binding site for aikylides, naturally only positions on the main body occur Question in which two H atoms can be replaced by the double bond, residues are eg = CH-CH 3,
=C(CH3)-CH3, =C(CH3)-C2H5 oder
Cycloalkyliden bedeutet ein carbocyclischer Rest, der über eine Zweifachbindung gebunden ist.
Der Begriff„Stannyl" steht für einen weiter substituierten Rest, der ein Zinn-Atom enthält;„Germanyl" steht analog für einen weiter substituierten Rest, der ein = C (CH 3 ) -CH 3 , = C (CH 3 ) -C 2 H 5 or Cycloalkylidene means a carbocyclic radical which is bonded via a double bond. The term "stannyl" stands for a further substituted radical containing a tin atom, "Germanyl" is analogous to a further substituted radical which is a
Germanium-Atom enthält.„Zirconyl" steht für einen weiter substituierten Rest, der ein Zirconium-Atom enthält.„Hafnyl" steht für einen weiter substituierten Rest, der ein Hafnium-Atom enthält.„Boryl",„Borolanyl" und„Borinanyl" steht für weiter substituierte und gegebenenfalls cyclische Gruppen, die jeweils ein Bor-Atom enthalten. "Zirconyl" represents a further substituted radical containing a zirconium atom. "Hafnyl" represents a further substituted radical containing a hafnium atom. "Boryl", "Borolanyl" and "Borinanyl". is further substituted and optionally cyclic groups, each containing a boron atom.
„Plumbanyl" steht für einen weiter substituierten Rest, der ein Blei-Atom enthält. "Plumbanyl" represents a further substituted radical containing a lead atom.
„Hydra rgyl" steht für einen weiter substituierten Rest, der ein Quecksilber-Atom enthält. „Alanyl" steht für einen weiter substituierten Rest, der ein Aluminium-Atom enthält. „Magnesyl" steht für einen weiter substituierten Rest, der ein Magnesium-Atom enthält. „Zinkyl" steht für einen weiter substituierten Rest, der ein Zink- Atom enthält. "Hydra rgyl" stands for a further substituted radical containing a mercury atom. "Alanyl" stands for a further substituted radical containing an aluminum atom. "Magnesyl" represents a further substituted radical containing a magnesium atom. "Zincyl" represents a further substituted radical containing a zinc atom.
Die Verbindungen der allgemeinen Formel (I) können je nach Art und Verknüpfung der Substituenten als Stereoisomere vorliegen. Die durch ihre spezifische Raumform definierten möglichen Stereoisomere, wie Enantiomere, Diastereomere, Z- und E- Isomere sind alle von der Formel (I) umfasst. Sind beispielsweise eine oder mehrere Alkenylgruppen vorhanden, so können Diastereomere (Z- und E-Isomere) auftreten. Sind beispielsweise ein oder mehrere asymmetrische Kohlenstoffatome vorhanden, so können Enantiomere und Diastereomere auftreten. Stereoisomere lassen sich aus den bei der Herstellung anfallenden Gemischen nach üblichen Trennmethoden erhalten. Die chromatographische Trennung kann sowohl im analytischen Maßstab zur Depending on the nature and linkage of the substituents, the compounds of the general formula (I) can exist as stereoisomers. The possible stereoisomers defined by their specific spatial form, such as enantiomers, diastereomers, Z and E isomers, are all encompassed by the formula (I). If, for example, one or more alkenyl groups are present, diastereomers (Z and E isomers) can occur. For example, if one or more asymmetric carbon atoms are present, enantiomers and diastereomers may occur. Stereoisomers can be obtained from the resulting mixtures in the preparation by conventional separation methods. The chromatographic separation can be used both on an analytical scale for
Feststellung des Enantiomerenüberschusses bzw. des Diastereomerenüberschusses, wie auch im präparativen Maßstab zur Herstellung von Prüfmustern für die biologische Ausprüfung erfolgen. Ebenso können Stereoisomere durch Einsatz stereoselektiver Reaktionen unter Verwendung optisch aktiver Ausgangs- und/oder Hilfsstoffe selektiv hergestellt werden. Die Erfindung betrifft somit auch alle Stereoisomeren, die von der allgemeinen Formel (I) umfasst, jedoch nicht mit ihrer spezifischen Stereoform angegeben sind, sowie deren Gemische
Synthese: Determination of the enantiomeric excess or of the diastereomeric excess, as also carried out on a preparative scale for the production of test samples for biological testing. Similarly, stereoisomers can be selectively prepared by using stereoselective reactions using optically active sources and / or adjuvants. The invention thus also relates to all stereoisomers which comprises the general formula (I) but are not specified with their specific stereoform, and mixtures thereof Synthesis:
Die erfindungsgemäßen 1 -(Arylethinyl)-, l -(Heteroarylethinyl)-, l -(Heterocyclylethinyl)- und 1 -(Cyloalkenylethinyl)- cyclohexanole der allgemeinen Formel (I) können ausgehend von bekannten Verfahren hergestellt werden (vgl. Qing et al. J. Fluorine Chem. 2000, 101 . 31 ; WO2009005794; Node et al. Bioorg. Med. Chem. 2007, 15, 2736; Schmidt et al. Can. J. Chem. 1973, 51 , 3620; Zhu et al. Org. Lett. 201 1 , 13, 684). Einige der darin beschriebenen Verfahren zur Synthese von Vinyl- und The 1 - (arylethynyl) -, 1- (heteroarylethynyl) -, 1- (heterocyclylethynyl) - and 1 - (cycloalkenylethynyl) cyclohexanols of the general formula (I) according to the invention can be prepared starting from known processes (compare Qing et al. J. Fluorine Chem. 2000, 101, 31; WO2009005794; Node et al., Bioorg. Med. Chem., 2007, 15, 2736; Schmidt et al., Can. J. Chem., 1973, 51, 3620; Zhu et al., Org Lett. 201 1, 13, 684). Some of the methods described therein for the synthesis of vinyl and
Alkinylcyclohexanolgrundgerüsten wurden optimiert und durch alternative Alkynylcyclohexanol backbones were optimized and replaced by alternative
Syntheseschritte ersetzt. Die eingesetzten und untersuchten Syntheserouten gehen dabei von kommerziell erhältlichen oder leicht herstellbaren Cyclohexanonen, Replaced synthesis steps. The synthetic routes used and investigated are based on commercially available or easily prepared cyclohexanones,
Heteroaryl- und Arylhalogeniden sowie Aryl-, Heteroaryl- und Alkenyltriflaten aus. Als ein Schlüsselintermediat für die Synthese der erfindungsgemäßen Verbindungen der allgemeinen Formel (I) wird ein entsprechend substituiertes und Heteroaryl and Arylhalogeniden and aryl, heteroaryl and Alkenyltriflaten from. As a key intermediate for the synthesis of the compounds of the general formula (I) according to the invention a correspondingly substituted and
Ethinylcyclohexanol hergestellt. Dazu wird ein entsprechend substituiertes Ethinylcyclohexanol produced. For this purpose, a correspondingly substituted
Cyclohexanon entweder direkt mit einem Lithiumacetylid-Ethylendiaminkomplex in einem geeigneten polar-aproti sehen Lösungsmittel (z. B. Tetrahydrofuran) oder in zwei Schritten durch Umsetzung mit Trimethylsilylacetylen und LDA Cyclohexanone either directly with a lithium acetylide-ethylenediamine complex in a suitable polar aprotic solvent (eg tetrahydrofuran) or in two steps by reaction with trimethylsilylacetylene and LDA
(Lithiumdiisopropylamid) in einem Temperaturbereich von -78 °C bis 0 °C in einem geeigneten polar-aproti sehen Lösungsmittel (z. B. THF = Tetrahydrofuran) und nachfolgende Abspaltung der Trimethylsilylgruppe mit Hilfe eines geeigneten (Lithium diisopropylamide) in a temperature range from -78 ° C to 0 ° C in a suitable polar-aproti see solvent (eg., THF = tetrahydrofuran) and subsequent cleavage of the trimethylsilyl using a suitable
Trialkylammoniumfluorids (z. B. Tetrabutylammoniumfluorid = TBAF) in einem polar- apro tischen Lösungsmittel oder mit einer geeigneten Carbonatbase (z. B. Trialkylammonium fluoride (eg tetrabutylammonium fluoride = TBAF) in a polar-organic solvent or with a suitable carbonate base (eg.
Kaliumcarbonat) in einem polar-proti sehen Lösungsmittel (z. B. Methanol) (vgl. J. Potassium carbonate) in a polar protic solvent (e.g., methanol) (see J. Chem.
Chem. Res. (S) 2003, 426) in das entsprechend substituierte Ethinylcyclohexanol überführt werden (Schema 1 ). Ausgehend von den obenen beschrieben und entsprechend substituierten Ethinylcyclohexanolen können die erfindungsgemäßen substituierten 1 -(Arylethinyl)-, l-(Heteroarylethinyl)-, l-(Heterocyclylethinyl)- und 1 - (Cyloalkenylethinyl)-cyclohexanole (1.1 ) durch Ubergangsmetall-kataiysierte Kupplung mit geeigneten substituierten Aryl-, Cycloalkenyl- und Heteroarylhalogeniden oder den entsprechenden Triflaten (vgl. J. Chem. Res. (S), 2003, 426; J. Chem. Soc, Perkin Trans. 1 2001 , 47; Adv. Synth. Catal. 2005, 347, 872; Synlett. 2010, 150; Org. Lett. 2008, 10, 1569; Helv. Chim. Acta 2009, 92, 826, Can. J. Chem. 1993, 71 , 983) unter Verwendung eines geeigneten Übergangsmetallkatalysatorsystems (z. B.
Bis(Triphenylphosphin)palladiumdichlond, Palladium(ll)acetat zusammen mit Chem. Res. (S) 2003, 426) are converted into the corresponding substituted ethynylcyclohexanol (Scheme 1). Starting from the above described and correspondingly substituted ethynylcyclohexanols, the substituted 1 - (arylethynyl) -, 1- (heteroarylethynyl) -, 1- (heterocyclylethynyl) - and 1 - (cycloalkenylethynyl) -cyclohexanols (1.1) according to the invention can be prepared by transition-metal-catalyzed coupling suitable substituted aryl, cycloalkenyl and heteroaryl halides or the corresponding triflates (see J. Chem. Res. (S), 2003, 426; J. Chem. Soc, Perkin Trans. 1 2001, 47; Adv. Synth. Catal. Synlett., 2010, 150; Org. Lett., 2008, 10, 1569; Helv. Chim. Acta 2009, 92, 826, Can. J. Chem., 1993, 71, 983) using a suitable transition metal catalyst system (eg Bis (triphenylphosphine) palladium dichloride, palladium (II) acetate together with
Triphenylphosphin oder Bis-(Cycloacta-1 ,5-dienyl)lridiumchiorid in Kombination mit einem bidentaten Liganden, z.B. 2.2'-Bis(diphenylphosphino)-1 ,1 '— binaphthyl oder 1 .4-bis-(diphenylphosphino)butan) und eines geeigneten Kupfer(l)halogenids (z. B. Kupfer(l)iodid) in einem geeigneten Losungsmittelgemisch aus einem Amin und einem polar aproti sehen Lösungsmittel (z. B. Diisopropylamin und Toluol oder Triethylamin und Tetra hydrofu ran) hergestellt werden (Schema 1 ). R1, R2, R3, R4, R6 und Q haben im folgenden Schema 1 die zuvor definierten Bedeutungen. Triphenylphosphine or bis (Cycloacta-1, 5-dienyl) lridiumchiorid in combination with a bidentate ligand, for example, 2.2 '-bis (diphenylphosphino) -1, 1' - binaphthyl or 1 .4-bis (diphenylphosphino) butane) and a suitable copper (I) halide (eg copper (I) iodide) in a suitable solvent mixture of an amine and a polar aprotic solvent (eg diisopropylamine and toluene or triethylamine and tetrahydrofuran) (Scheme 1 ). R 1 , R 2 , R 3 , R 4 , R 6 and Q in the following Scheme 1 have the meanings defined above.
X = Gl, Br, I, OTf X = Gl, Br, I, OTf
Schema 1 . Scheme 1.
Alternativ können die erfindungsgemäßen substituierten 1 -(Arylethinyl)-, 1 - (Heteroarylethinyl)-, 1 -(Heterocyclylethinyl)- und 1 -(Cyloalkenylethinyl)-cyclohexanole (1.1 ) durch Indiumsalz vermittelte Addition (z. B. mit lndium(l ll)trifluormethansulfonat, lndium(lll)bromid, lndium(lll)chlorid, Indium(l ll)iodid) eines entsprechend substituierten Aryl-, Cycloalkenyl- oder Heteroarylalkins an ein entsprechend substituiertes Alternatively, the substituted 1 - (arylethynyl) -, 1- (heteroarylethynyl) -, 1- (heterocyclylethynyl) - and 1- (cycloalkenylethynyl) -cyclohexanols (1.1) according to the invention can be added by indium salt-mediated addition (eg with indium (II trifluoromethanesulfonate, indium (III) bromide, indium (III) chloride, indium (II) iodide) of an appropriately substituted aryl, cycloalkenyl or heteroaryl alkyne to an appropriately substituted one
Cyclohexanon unter Verwendung einer geeigneten Aminbase (z. B. Diisopropylamin, Triethylamin, Diisopropylethylamin, Bis-cyclohexyl(methyl)amin, N-Methylpiperidin, 1 ,8-Diazabicyclo[5.4.0]undec-7-en) in einem geeigneten polar-aprotischen Cyclohexanone using a suitable amine base (eg diisopropylamine, triethylamine, diisopropylethylamine, biscyclohexyl (methyl) amine, N-methylpiperidine, 1,8-diazabicyclo [5.4.0] undec-7-ene) in a suitable polar aprotic
Lösungsmittel (z. B. Dimethoxyethan = DME, Dichlormethan = DCM, Dichlorethan, Toluol, Cyclohexan) hergestellt werden (Schema 2). R1, R2, R3, R4, R6 und Q haben im folgenden Schema 2 die zuvor definierten Bedeutungen. Das dabei verwendete weiter substituierte Aryl-, Cycloalkenyl- oder Heteroarylalkin kann ausgehend von den entsprechenden Triflaten durch eine Palladium-Katalysator vermittelte Kupplung mit Trimethylsilylacetylen hergestellt werden (vgl. Org. Lett. 2005, 7, 1363).
Solvents (eg, dimethoxyethane = DME, dichloromethane = DCM, dichloroethane, toluene, cyclohexane) are prepared (Scheme 2). R 1 , R 2 , R 3 , R 4 , R 6 and Q in the following Scheme 2 have the meanings defined above. The further substituted aryl, cycloalkenyl or heteroarylalky used here can be prepared starting from the corresponding triflates by a palladium catalyst-mediated coupling with trimethylsilylacetylene (compare Org. Lett. 2005, 7, 1363).
Schema 2. Die erfindungsgemäßen substituierten l -(Arylethinyl)-, 1 -(Heteroarylethinyl)-, 1- (Heterocyclylethinyl)- und 1-(Cyloalkenyiethinyl)-cyclohexanole (1.1 ) können durch Folgeraktionen in die entsprechenden Analoga (I.2) bis (I.6) überführt werden. Die Hydroxygruppe der betreffenden erfindungsgemäßen substituierten Scheme 2. The substituted 1 - (arylethynyl) -, 1 - (heteroarylethynyl) -, 1- (heterocyclylethynyl) - and 1- (cycloalkenylthioyl) cyclohexanols (1.1) according to the invention can be prepared by subsequent reactions in the corresponding analogs (I.2) to (I.6). The hydroxy group of the relevant substituted according to the invention
Alkinylcyclohexanole (1.1 ) kann durch Umsetzung mit einem geeigneten Alkynylcyclohexanols (1.1) can be prepared by reaction with a suitable
Silyltrifluormethansulfonat-Reagenz (z. B. Triethylsilylmethansulfonat = TES-OTf) unter Verwendung einer geeigneten Base (z. B. 2,6-Lutidin) in einem geeigneten polar- aprotischen Lösungsmittel (z. B. Dichlormethan) in ein substituiertes 1 - Ethinylcyclohexyloxy(alkyl)silan (I.2) überführt werden. Stellvertretend wird diese Umsetzung in Schema 3 unter Verwendung von Triethylsilyltrifluormethansulfonat beschrieben. Die Umsetzung eines erfindungsgemäßen substituierten Silyl trifluoromethanesulfonate reagent (eg, triethylsilyl methanesulfonate = TES-OTf), using a suitable base (e.g., 2,6-lutidine) in a suitable polar aprotic solvent (e.g., dichloromethane) to a substituted 1-ethynylcyclohexyloxy (alkyl) silane (I.2) are transferred. By way of illustration, this reaction is described in Scheme 3 using triethylsilyl trifluoromethanesulfonate. The reaction of a substituted according to the invention
Alkinylcyclohexanois (1.1 ) mit einem geeigneten Acylchlorid (exemplarisch in Schema 3 gezeigt durch die Reaktion mit Acetylchlorid) und einer geeigneten Aminbase (z. B. Triethylamin, Dimethylaminopyridin) in einem polar-aprotischen Lösungsmittel (z. B. Tetra hydrofu ran oder Dichlormethan) liefert die substituierten erfindungsgemäßen Verbindungen (I.2).
Alkynylcyclohexanois (1.1) with a suitable acyl chloride (exemplified in Scheme 3 by the reaction with acetyl chloride) and a suitable amine base (eg triethylamine, dimethylaminopyridine) in a polar aprotic solvent (eg tetrahydrofuran or dichloromethane) provides the substituted compounds of the invention (I.2).
Schema 3. Scheme 3.
Durch Reaktion eines erfindungsgemäßen substituierten Alkinylcyclohexanois (1.1 ) mit einem geeigneten Gold-Katalysator (z. B. Gold(lll)bromid, Gold(lll)chlorid, By reaction of a substituted alkynylcyclohexanois (1.1) according to the invention with a suitable gold catalyst (for example gold (III) bromide, gold (III) chloride,
Natriumtetrachloroaurat, Tetrachlorogoldsäure) und einem geeigneten nukleophilen Reaktionspartner (exemplarisch in Schema 3 gezeigt mit n-Butanol,) in einem geeigneten polar-aproti sehen Lösungsmittel (z. B. Tetrahydrofuran, Dichlormethan) können die entsprechenden substituierten Ethinylcyclohexane (I.4) erhalten werden (vgl. auch J. Am. Chem. Soc. 2005, 127, 14181 ). R\ R2, R3, R4, R6 und Q haben in Schema 3 die zuvor definierten Bedeutungen. Sodium tetrachloroaurate, tetrachloroauric acid) and a suitable nucleophilic reactant (exemplified in Scheme 3 with n-butanol) in a suitable polar-aprotic solvent (eg, tetrahydrofuran, dichloromethane), the corresponding substituted ethynylcyclohexanes (I.4) can be obtained (See also J. Am. Chem. Soc. 2005, 127, 14181). R 1 , R 3 , R 4 , R 6 and Q in Scheme 3 have the meanings defined above.
Die erfindungsgemäßen substituierten (E)-konfigurierten 1 -Arylvinyl-, 1 - Heteroarylvinyl-, 1-Cycloalkenylvinylcyclohexanole (I.5) können durch Reduktion der Aikingruppe der entsprechenden substituierten 1 -(Arylethinyl)-, 1 -(Heteroarylethinyl)-, 1 -(Heterocyclylethinyl)- und 1 -(Cyloalkenylethinyl)-cyclohexanole (1.1 ) unter The substituted (E) -configured 1-arylvinyl-, 1-heteroarylvinyl-, 1-cycloalkenylvinylcyclohexanols (I.5) according to the invention can be prepared by reduction of the Aicyruppe of the corresponding substituted 1- (arylethynyl) -, 1 - (heteroarylethynyl) -, 1 - (Heterocyclylethynyl) - and 1 - (cycloalkenylethynyl) cyclohexanols (1.1)
Verwendung geeigneter Aluminiumhydridreagenzien (z. B. Natrium-bis-(2- methoxyethoxy)-aluminiumhydrid oder Lithiumaluminiumhydrid) in einem geeigneten polar-aprotischen Lösungsmittel (z. B. Tetrahydrofuran) (vgl. Org. Biomol. Chem.
2006, 4, 4186; Bioorg. Med. Chem. 2004, 12. 363-370; Tetrahedron 2003, 59, 9091 - 9100; Org. Biomol. Chem. 2006, 4, 1400-1412; Synthesis 1977, 561 ; Tetrahedron Letters 1992, 33, 3477 und Tetrahedron Letters 1974, 1593), unter Einsatz von Use of suitable aluminum hydride reagents (eg sodium bis (2-methoxyethoxy) aluminum hydride or lithium aluminum hydride) in a suitable polar aprotic solvent (eg tetrahydrofuran) (see Org. Biomol. Chem. 2006, 4, 4186; Bioorg. Med. Chem. 2004, 12, 363-370; Tetrahedron 2003, 59, 9091 - 9100; Org. Biomol. Chem. 2006, 4, 1400-1412; Synthesis 1977, 561; Tetrahedron Letters 1992, 33, 3477 and Tetrahedron Letters 1974, 1593), using
Borhydridreagenzien (z. B. Natriumborhydrid) in einem geeigneten polar-protischen Lösungsmittel (z. B. Methanol) (vgl. Org. Lett. 2004, 6, 1785), unter Verwendung von Lithium gelöst in einem Gemisch aus Ethylamin und tert.-Butanol (z. B. Helvetica Chimica Acta 1986, 69, 368) oder unter Nutzung eines geeigneten Trialkoxysilans in Gegenwart eines geeigneten Übergangsmetallkatalysators (z. B. Tris- (acetonitril)ruthenium-l ,2.3,4.5-pentamethylcyclopentadienylhexafluorophosphat oder Tris-(acetonitril)ruthenium-cyclopentadienylhexafluorophosphat; vgl. J. Am. Chem. Soc. 2002, 124, 7622; J. Am. Chem. Soc. 2005, 127, 17645) hergestellt werden (Schema 4). Eine weitere Variante zur Reduktion der Alkingruppe stellt die Umsetzung des betreffenden Alkins mit Zink in konz. Essigsäure oder mit Zink und einem passenden Ammoniumsalz in einem geeigneten polar-aprotischen Lösungsmittel (z. B. Dichlormethan) dar (vgl. WO2006027243). In Abhängigkeit von den Borohydride reagents (eg sodium borohydride) in a suitable polar protic solvent (eg methanol) (see Org. Lett 2004, 6, 1785), using lithium dissolved in a mixture of ethylamine and tert. Butanol (eg Helvetica Chimica Acta 1986, 69, 368) or using an appropriate trialkoxysilane in the presence of a suitable transition metal catalyst (eg tris (acetonitrile) ruthenium-l, 2,3,4,5-pentamethylcyclopentadienylhexafluorophosphate or tris (acetonitrile Ruthenium cyclopentadienyl hexafluorophosphate, see J. Am. Chem. Soc., 2002, 124, 7622; J. Am. Chem. Soc., 2005, 127, 17645) (Scheme 4). Another variant for the reduction of the alkyne group is the reaction of the respective alkyne with zinc in conc. Acetic acid or with zinc and a suitable ammonium salt in a suitable polar aprotic solvent (eg dichloromethane) (see WO2006027243). Depending on the
Reaktionsbedingungen können bei den Hydrierungen der Dreifachbindung als weitere Reaktionsprodukte auch die entsprechenden erfindungsgemäßen (Z)-konfigurierten Analoga erhalten werden. R1, R2, R3, R4, R5, R6 und Q haben in Schema 4 die zuvor definierten Bedeutungen. Die Reduktion von erfindungsgemäßen substituierten 1- (Arylethinyl)-, 1 -(Heteroarylethinyl)-, 1 -(Heterocyclylethinyl)- und 1 -(Cyloalkenylethinyl)- cyclohexanolen (1.1 ) zu den erfindungsgemäßen substituierten (Z)-konfigurierten 1 - Arylvinyl-, 1 -Heteroarylvinyl-, 1-Cycloalkenylvinylcyclohexanolen (I.6) läßt sich in Gegenwart eines Übergangsmetallkatalysators wie zum Beispiel Lindlars Katalysator mit Wasserstoff in einem geeigneten polar-aprotischen Lösungsmittel (wie z. B. n- Butanol) durchführen (vgl. Tetrahedron 1987, 43, 4107; Tetrahedron 1983, 39, 2315; J. Org. Synth. 1983, 48, 4436 und J. Am. Chem. Soc. 1984, 106, 2735) (Schema 5). R1, R2, R3, R4, R5, R6 und Q haben in Schema 5 die zuvor definierten Bedeutungen. Reaction conditions can be obtained in the hydrogenation of the triple bond as further reaction products and the corresponding inventive (Z) -configured analogs. R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and Q have the previously defined meanings in Scheme 4. The reduction of substituted 1- (arylethynyl) -, 1- (heteroarylethynyl) -, 1- (heterocyclylethynyl) - and 1 - (cycloalkenylethynyl) -cyclohexanols (1.1) according to the invention to the substituted (Z) -configured 1-arylvinyl-, 1-heteroarylvinyl, 1-cycloalkenylvinylcyclohexanols (I.6) can be reacted with hydrogen in the presence of a transition metal catalyst such as Lindlar's catalyst in a suitable polar aprotic solvent (such as n-butanol) (see Tetrahedron 1987, 43, 4107; Tetrahedron 1983, 39, 2315; J. Org. Synth. 1983, 48, 4436 and J. Am. Chem. Soc. 1984, 106, 2735) (Scheme 5). R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and Q have the previously defined meanings in Scheme 5.
Schema 5.
Falls Re in den erfindungsgemäßen substituierten l-(Arylethinyl)-, 1- (Heteroarylethinyl)-, 1 -(Heterocyclylethinyl)- und 1 -(Cyloalkenylethinyl)-cyclohexanolen (1.1 ) für eine Carboxyl- oder Formylgruppe steht, ergeben sich weitere Scheme 5. If Re in the substituted 1- (arylethynyl) -, 1- (heteroarylethynyl) -, 1- (heterocyclylethynyl) - and 1- (cycloalkenylethynyl) -cyclohexanols (1.1) according to the invention is a carboxyl or formyl group, further results
Reaktionsmöglichkeiten. Die Carbonsäurefunktion kann mit Aminen oder Aminosäuren unter Verwendung von geeigneten Kupplungsreagenzien (z. B. 1 -Hydroxybenzotriazol = HOBt; 1 -Ethyl-3-(3-dimethylaminopropyl)carbodiimid = EDC; Response options. The carboxylic acid function can be carried out with amines or amino acids using suitable coupling reagents (e.g., 1-hydroxybenzotriazole = HOBt; 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide = EDC;
Dicyclohexylcarbodiimid = DCC; Benzotriazolyloxytris[dimethylamino]- 10-phosphoniumhexafluorophosphat = BOP; 2-(1 H-benzotriazol-1 -yl_)-1.1.3.3- tetramethyluroniumhexafluorophosphat = HBTU; 2-(7-Aza-1 H-benzotriazole-1 -yl)-1 , 1 ,3,3- tetramethyluronium hexafluorophosphat = HATU) und einer geeigneten Base (z. B. Triethylamin, Diisopropylethylamin) in einem geeigneten polar-aprotischen Dicyclohexylcarbodiimide = DCC; Benzotriazolyloxytris [dimethylamino] - 10-phosphonium hexafluorophosphate = BOP; 2- (1H-benzotriazol-1-yl) -1,1,3,3-tetramethyluronium hexafluorophosphate = HBTU; 2- (7-aza-1H-benzotriazole-1-yl) -1, 1, 3,3-tetramethyluronium hexafluorophosphate (HATU) and a suitable base (e.g., triethylamine, diisopropylethylamine) in a suitable polar aprotic
Lösungsmittel (z. B. Tetrahydrofuran, Dichlormethan) in ein entsprechendes erfindungsgemäßes Amid (I.7) überführt werden. Diese Umsetzung wird in Schema 6 exemplarisch am Beispiel von Glycin gezeigt. Die Formylfunktion kann mit einem gegebenenfalls weiter substituierten Hydroxylamin unter Verwendung einer geeigneten Base (z. B. Natriumacetat) in einem geeigneten polar-aprotischen Lösungsmittel (z. B. Dichlormethan, Tetrahydrofuran, Acetonitril) in entsprechendes erfindungsgemäßes Hydroxylamin (I.8) überführt werden. Diese Umsetzung wird in Schema 6 Solvent (eg., Tetrahydrofuran, dichloromethane) are converted into a corresponding inventive amide (I.7). This reaction is shown in Scheme 6 using the example of glycine as an example. The formyl function can be converted with an optionally further substituted hydroxylamine using a suitable base (eg sodium acetate) in a suitable polar aprotic solvent (eg dichloromethane, tetrahydrofuran, acetonitrile) into corresponding hydroxylamine (I.8) according to the invention , This implementation is shown in Scheme 6
exemplarisch unter Verwendung von H3C-CH2-O-NH2 gezeigt. R1, R2, R3, R4, R5 und Q haben im folgenden Schema 6 die zuvor definierten Bedeutungen. exemplified using H3C-CH2-O-NH2. R 1 , R 2 , R 3 , R 4 , R 5 and Q in the following Scheme 6 have the meanings defined above.
Schema 6.
Ausgewählte detaillierte Synthesebeispiele für die erfindungsgemäßen Verbindungen der allgemeinen Formel (I) sind im Folgenden aufgeführt. Die angegebenen Scheme 6. Selected detailed synthesis examples of the compounds of the general formula (I) according to the invention are listed below. The specified
Beispielnummern entsprechen den in den nachstehenden Tabellen 1 bis XX genannten Numerierungen. Die 1H-NMR-, 13C-NMR- und 9F-NMR-spektroskopischen Daten, die für die in den nachfolgenden Abschnitten beschriebenen chemischen Beispiele angegeben sind, (400 MHz bei 1H-NMR und 150 MHz bei 13C-NMR und 375 MHz bei 9F-NMR, Lösungsmittel CDCh, CD3OD oder d6-DMSO, interner Standard: Tetramethylsilan δ = 0.00 ppm), wurden mit einem Gerät der Firma Bruker erhalten, und die bezeichneten Signale haben die nachfolgend aufgeführten Bedeutungen: br = breit(es); s = Singulett, d = Dublett, t = Triplett, dd = Doppeldublett, ddd = Dublett eines Doppeldubletts, m = Multiplett, q = Quartett, quint = Quintett, sext = Sextett, sept = Septett, dq = Doppelquartett, dt = Doppeltriplett, tt = dreifaches Triplett. Bei Example numbers correspond to the numbers given in Tables 1 to XX below. The 1 H NMR, 13 C NMR and 9 F NMR spectroscopic data reported for the chemical examples described in the following sections (400 MHz for 1 H NMR and 150 MHz for 13 C NMR and 375 MHz at 9 F-NMR, solvent CDCh, CD 3 OD or d 6 -DMSO, internal standard: tetramethylsilane δ = 0.00 ppm), were obtained with a Bruker instrument and the indicated signals have the following meanings: br = broad (it); s = singlet, d = doublet, t = triplet, dd = double doublet, ddd = doublet of double doublet, m = multiplet, q = quartet, quint = quintet, sext = sextet, sept = septet, dq = double quartet, dt = double triplet, tt = triple triplet. at
Diastereomerengemischen werden entweder die jeweils signifikanten Signale beider Diastereomere oder das charakteristische Signal des Hauptdiastereomers angegeben. Die verwendeten Abkürzungen für chemische Gruppen haben die nachfolgenden Bedeutungen: Me = CH3, Et = CH2CH3, t-Hex = C(CH3)2CH(CH3)2, t-Bu = C(CH3)3, n- Bu = unverzweigtes Butyl, n-Pr = unverzweigtes Propyl, c-Hex = Cyclohexyl. No. 1.1 -54: 1 -[(2-Methoxyphenyl)ethinyl]-2.2,6-trimethylcyclohexanol Diastereomeric mixtures are given either the respectively significant signals of both diastereomers or the characteristic signal of the main diastereomer. The abbreviations used for chemical groups have the following meanings: Me = CH 3 , Et = CH 2 CH 3 , t-Hex = C (CH 3 ) 2 CH (CH 3 ) 2 , t-Bu = C (CH 3 ) 3 , n-Bu = unbranched butyl, n-Pr = unbranched propyl, c-hex = cyclohexyl. No. 1.1-54: 1 - [(2-methoxyphenyl) ethynyl] -2,2,6-trimethylcyclohexanol
2,2,6-Trimethylcyclohexanon (200 mg, 1 .43 mmol) wurde in einem Rundkolben unter Argon in abs. Tetrahydrofuran (3 ml) gelöst und tropfenweise zu einer Lösung eines Lithiumacetylid-Ethylendiaminkomplexes (171 mg, 1 .85 mmol, 85% Gehalt) in abs. Tetrahydrofuran (2 ml) gegeben. Die Reaktionslösung wurde nach erfolgter Zugabe 2 h lang bei Raumtemperatur gerührt, anschließend mit Wasser versetzt und unter vermindertem Druck eingeengt. Der verbleibende Rückstand wurde mit Wasser und Dichlormethan versetzt und die wässrige Phase mehrfach mit Dichlormethan extrahiert. Die vereinigten organischen Phasen wurden über Magnesiumsulfat
getrocknet, filtriert und unter vermindertem Druck eingeengt. Durch 2,2,6-Trimethylcyclohexanone (200 mg, 1.43 mmol) was dissolved in a round bottom flask under argon in abs. Tetrahydrofuran (3 ml) was dissolved and added dropwise to a solution of a lithium acetylide-ethylenediamine complex (171 mg, 1.85 mmol, 85% content) in abs. Tetrahydrofuran (2 ml). The reaction solution was stirred for 2 h after the addition at room temperature, then treated with water and concentrated under reduced pressure. The remaining residue was mixed with water and dichloromethane and the aqueous phase extracted several times with dichloromethane. The combined organic phases were over magnesium sulfate dried, filtered and concentrated under reduced pressure. By
säulenchromatographische Reinigung des erhaltenen Rohproduktes (Gradient column-chromatographic purification of the crude product obtained (gradient
Essigester/Heptan) wurde 1 -Ethinyl-2,2,6-trimethylcyclohexanol (201 mg, 85 % der Theorie) als farbloser wachsartiger Feststoff isoliert. Anschließend wurden Ethyl acetate / heptane), 1-ethynyl-2,2,6-trimethylcyclohexanol (201 mg, 85% of theory) was isolated as a colorless waxy solid. Subsequently were
Kupfer(l)iodid (46 mg, 0.24 mmol) und Bis(triphenylphosphin)palladium(ll)chlorid (127 mg, 0.18 mmol) unter Argon in einem ausgeheizten Rundkolben vorgelegt und mit abs. Toluol (6 ml) sowie 2-Methoxyiodbenzol (282 mg, 1 .20 mmol) versetzt. Nach 10 Min Rühren bei Raumtemperatur erfolgte die tropfenweise Zugabe einer Lösung von 1 - Ethinyl-2,2,6-trimethylcyclohexanol (200 mg, 1 .20 mmol) in abs. Toluol (4 ml) und von Diisopropylamin (0.34 ml, 2.41 mmol). Das resultierende orangefarbene Copper (I) iodide (46 mg, 0.24 mmol) and bis (triphenylphosphine) palladium (II) chloride (127 mg, 0.18 mmol) under argon in a heated round bottom flask and charged with abs. Toluene (6 ml) and 2-methoxyiodobenzene (282 mg, 1 .20 mmol) were added. After stirring for 10 minutes at room temperature, the dropwise addition of a solution of 1-ethynyl-2,2,6-trimethylcyclohexanol (200 mg, 1 .20 mmol) in abs. Toluene (4 ml) and diisopropylamine (0.34 ml, 2.41 mmol). The resulting orange
Reaktionsgemisch wurde 4 h lang bei Raumtemperatur gerührt und danach mit Wasser versetzt. Die wässrige Phase wurde mehrfach mit Dichlormethan extrahiert. Die vereinigten organischen Phasen wurden über Magnesiumsulfat getrocknet, filtriert und unter vermindertem Druck eingeengt. Durch abschließende The reaction mixture was stirred for 4 h at room temperature and then treated with water. The aqueous phase was extracted several times with dichloromethane. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. By final
säulenchromatographische Reinigung des erhaltenen Rohproduktes (unter column chromatographic purification of the resulting crude product (under
Verwendung eines Essigester/Heptan-Gradienten) wurde 1 -[(2- Methoxyphenyl)ethinyl]-2,2,6-trimethylcyclohexanol (215 mg, 66 % der Theorie) in Form eines schwach gelblichen Feststoffes isoliert. H-NMR (400 MHz, CDC δ, ppm) 7.91 (d, 1 H), 7.57 (d, 1 H), 7.45 (t, 1 H), 7.36 (t, 1 H), 3.91 (s, 3H), 2.15 (s, 1 H), 1 .96 (m, 1 H), 1 .72 (m, 1 H), 1 .62 (m, 1 H), 1 .48 (m, 3H), 1 .39 (m, 1 H), 1 .21 (s, 3H), 1 .12 (d, 3H), 1 .06 (s, 3H). Using an ethyl acetate / heptane gradient), 1 - [(2-methoxyphenyl) ethynyl] -2,2,6-trimethylcyclohexanol (215 mg, 66% of theory) was isolated as a pale yellowish solid. H-NMR (400 MHz, CDC δ, ppm) 7.91 (d, 1H), 7.57 (d, 1H), 7.45 (t, 1H), 7.36 (t, 1H), 3.91 (s, 3H) , 2.15 (s, 1H), 1 .96 (m, 1H), 1 .72 (m, 1H), 1 .62 (m, 1H), 1 .48 (m, 3H), 1. 39 (m, 1H), 1 .21 (s, 3H), 1 .12 (d, 3H), 1 .06 (s, 3H).
No. 1.1 -1 16: Methyl-2-[(1-hydroxy-2.2,6-trimethylcyclohexyl)ethinyl]benzoat No. 1.1-1 16: methyl 2 - [(1-hydroxy-2,2,6-trimethylcyclohexyl) ethynyl] benzoate
2.2,6-Trimethylcyclohexanon (200 mg, 1 .43 mmol) wurde in einem Rundkolben unter Argon in abs. Tetra hydrofu ran (3 ml) gelöst und tropfenweise zu einer Lösung eines Lithiumacetylid-Ethylendiaminkomplexes (171 mg, 1 .85 mmol, 85% Gehalt) in abs. Tetra hydrofu ran (20 ml) gegeben. Die Reaktionslösung wurde nach erfolgter Zugabe 2 h lang bei Raumtemperatur gerührt, anschließend mit Wasser versetzt und unter
vermindertem Druck eingeengt. Der verbleibende Rückstand wurde mit Wasser und Dichlormethan versetzt und die wässrige Phase mehrfach mit Dichlormethan extrahiert. Die vereinigten organischen Phasen wurden über Magnesiumsulfat getrocknet, filtriert und unter vermindertem Druck eingeengt. Durch 2,2,6-Trimethylcyclohexanone (200 mg, 1 .43 mmol) was dissolved in a round bottom flask under argon in abs. Tetra hydrofu ran (3 ml) and added dropwise to a solution of a Lithiumacetylid-ethylenediamine complex (171 mg, 1 .85 mmol, 85% content) in abs. Tetrahydrofuran (20 ml). After the addition had taken place, the reaction solution was stirred for 2 hours at room temperature, then treated with water and taken under concentrated reduced pressure. The remaining residue was mixed with water and dichloromethane and the aqueous phase extracted several times with dichloromethane. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. By
säulenchromatographische Reinigung des erhaltenen Rohproduktes (Gradient column-chromatographic purification of the crude product obtained (gradient
Essigester/Heptan) wurde 1 -Ethinyl-2,2.6-trimethylcyclohexanol (205 mg, 87 % der Theorie) als farbloser wachsartiger Feststoff isoliert. Anschließend wurden Ethyl acetate / heptane), 1-ethynyl-2,2,6-trimethylcyclohexanol (205 mg, 87% of theory) was isolated as a colorless waxy solid. Subsequently were
Kupfer(l)iodid (46 mg, 0.24 mmol) und Bis(thphenylphosphin)palladium(ll)chlorid (127 mg, 0.18 mmol) unter Argon in einem ausgeheizten Rundkolben vorgelegt und mit abs. Toluol (6 ml) sowie Methyl-2-lodbenzoat (315 mg, 1 .20 mmol) versetzt. Nach 10 Min Rühren bei Raumtemperatur erfolgte die tropfenweise Zugabe einer Lösung von 1 - Ethinyl-2,2.6-trimethylcyclohexanol (200 mg, 1 .20 mmol) in abs. Toluol (4 ml) und von Diisopropylamin (0.34 ml, 2.41 mmol). Das resultierende orangefarbene Copper (I) iodide (46 mg, 0.24 mmol) and bis (thphenylphosphine) palladium (II) chloride (127 mg, 0.18 mmol) under argon in a heated round bottom flask and charged with abs. Toluene (6 ml) and methyl 2-iodobenzoate (315 mg, 1 .20 mmol) were added. After stirring for 10 min at room temperature, the dropwise addition of a solution of 1-ethynyl-2,2,6-trimethylcyclohexanol (200 mg, 1 .20 mmol) in abs. Toluene (4 ml) and diisopropylamine (0.34 ml, 2.41 mmol). The resulting orange
Reaktionsgemisch wurde 4 h lang bei Raumtemperatur gerührt und danach mit Wasser versetzt. Die wässrige Phase wurde mehrfach mit Dichlormethan extrahiert. Die vereinigten organischen Phasen wurden über Magnesiumsulfat getrocknet, filtriert und unter vermindertem Druck eingeengt. Durch abschließende The reaction mixture was stirred for 4 h at room temperature and then treated with water. The aqueous phase was extracted several times with dichloromethane. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. By final
säulenchromatographische Reinigung des erhaltenen Rohproduktes (unter column chromatographic purification of the resulting crude product (under
Verwendung eines Essigester/Heptan-Gradienten) wurde Methyl-2-[(1 -hydroxy-2.2,6- trimethylcyclohexyl)ethinyl]benzoat (210 mg, 58 % der Theorie) in Form eines schwach gelblichen Feststoffes isoliert. Ή-NMR (400 MHz, CDC 6, ppm) 7.91 (d, 1 H), 7.57 (d, 1 H), 7.45 (dd, 1 H), 7.35 (dd, 1 H), 3.91 (s, 3H), 2.16 (s, 1 H), 1 .97 (m, 1 H), 1 .72 (m, 1 H), 1 .67-1 .42 (m, 5H), 1 .20 (s, 3H), 1 .13 (d. 3H), 1 .08 (s, 3H); 3C-NMR (150 MHz, d6- DMSO δ, ppm) 166.5, 134.0, 131 .9, 131 .8, 129.6, 128.1 , 122.5, 96.3, 83.9, 77.2, 52.4, 40.1 . 37.4, 36.8, 32.1 . 27.0, 20.9. 19.9, 16.8. Diastereomer 2 - H-NMR (600 MHz, d6- DMSO δ, ppm) 7.82 (d, 1 H), 7.58 (d, 1 H), 7.56 (dd, 1 H), 7.47 (dd. 1 H), 4.84 (br. S, 1 H, OH). 3.84 (s, 3H), 1 .91 (m, 1 H), 1 .61 (m, 1 H), 1 .57-1 .32 (m. 4H), 1 .12 (s, 3H), 1 .10 (s, 3H), 1 .08 (d, 3H), 0.98 (m, 1 H); 3C-NMR (150 MHz, d6-DMSO δ, ppm) 166.4, 133.9, 131 .9, 131 .8, 129.6, 128.1 , 122.5, 98.1 , 82.2, 74.7, 52.3, 38.4, 36.1 . 33.4, 28.5, 26.6, 23.4. 20.7. 17.3.
No. 1.1 -107: 2-[(1 -Hydroxy-2,2,6-trimethylcyclohexyl)ethinyl]benzoesäure Using an ethyl acetate / heptane gradient), methyl 2 - [(1-hydroxy-2,2,6-trimethylcyclohexyl) ethynyl] benzoate (210 mg, 58% of theory) was isolated as a pale yellowish solid. Ή-NMR (400 MHz, CDC 6, ppm) 7.91 (d, 1H), 7.57 (d, 1H), 7.45 (dd, 1H), 7.35 (dd, 1H), 3.91 (s, 3H) , 2.16 (s, 1H), 1 .97 (m, 1H), 1 .72 (m, 1H), 1 .67-1 .42 (m, 5H), 1 .20 (s, 3H) , 1 .13 (i.e., 3H), 1 .08 (s, 3H); 3 C-NMR (150 MHz, d 6 -DMSO δ, ppm) 166.5, 134.0, 131 .9, 131 .8, 129.6, 128.1, 122.5, 96.3, 83.9, 77.2, 52.4, 40.1. 37.4, 36.8, 32.1. 27.0, 20.9. 19.9, 16.8. Diastereomer 2 - H-NMR (600 MHz, d 6 - DMSO δ, ppm) 7.82 (d, 1 H), 7.58 (d, 1 H), 7.56 (dd, 1 H), 7.47 (dd 1 H), 4.84 (br, S, 1H, OH). 3.84 (s, 3H), 1 .91 (m, 1H), 1 .61 (m, 1H), 1 .57-1 .32 (m 4H), 1 .12 (s, 3H), 1 .10 (s, 3H), 1 .08 (d, 3H), 0.98 (m, 1H); 3 C NMR (150 MHz, d 6 -DMSO δ, ppm) 166.4, 133.9, 131 .9, 131 .8, 129.6, 128.1, 122.5, 98.1, 82.2, 74.7, 52.3, 38.4, 36.1. 33.4, 28.5, 26.6, 23.4. 20.7. 17.3. No. 1.1-107: 2 - [(1-Hydroxy-2,2,6-trimethylcyclohexyl) ethynyl] benzoic acid
Methyl-2-[(1 -hydroxy-2!2,6-trimethylcyclohexyl)ethinyl]benzoat (2000 mg, 6.66 mmol) wurde in Ethanol (7 ml) gelöst und mit Wasser (40 ml) sowie fein gepulvertem Methyl 2 - [(1-hydroxy-2 : 2,6-trimethylcyclohexyl) ethynyl] benzoate (2000 mg, 6.66 mmol) was dissolved in ethanol (7 ml) and washed with water (40 ml) and finely powdered
Natriumhydroxid (799 mg, 19.97 mmol) versetzt. Das resultierende Reaktionsgemisch wurde 2 h lang unter Rückflußbedingungen gerührt und nach dem Abkühlen auf Raumtemperatur mit Wasser versetzt und mit verd. Salzsäure auf pH7 eingestellt. Die wässrige Phase wurde mehrfach mit Dichlormethan extrahiert. Die vereinigten organischen Phasen wurden über Magnesiumsulfat getrocknet, filtriert und unter vermindertem Druck eingeengt. Durch abschließende säulenchromatographische Reinigung des erhaltenen Rohproduktes (unter Verwendung eines Essigester/Heptan- Gradienten) wurde 2-[(1 -Hydroxy-2,2,6-trimethylcyclohexyl)ethinyl]benzoesäure (1700 mg, 89 % der Theorie) in Form eines farblosen Feststoffes isoliert. H-NMR (400 MHz, CDC 6, ppm) 8.08 (d, 1 H), 7.60 (d, 1 H), 7.51 (dd, 1 H), 7.40 (dd, 1 H), 1 .98 (m, 1 H), 1 .75 (m, 1 H), 1 .62 (m, 1 H), 1 .50 (m, 3H), 1 .39 (m, 1 H), 1 .20 (s, 3H), 1 .12 (d, 3H), 1 .08Sodium hydroxide (799 mg, 19.97 mmol) was added. The resulting reaction mixture was stirred for 2 hours under reflux conditions and, after cooling to room temperature, treated with water and adjusted to pH 7 with dilute hydrochloric acid. The aqueous phase was extracted several times with dichloromethane. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. Final purification by column chromatography of the resulting crude product (using an ethyl acetate / heptane gradient) gave 2 - [(1-hydroxy-2,2,6-trimethylcyclohexyl) ethynyl] benzoic acid (1700 mg, 89% of theory) as a colorless Solid isolated. H-NMR (400 MHz, CDC 6, ppm) 8.08 (d, 1H), 7.60 (d, 1H), 7.51 (dd, 1H), 7.40 (dd, 1H), 1.98 (m, 1 H), 1 .75 (m, 1 H), 1 .62 (m, 1 H), 1 .50 (m, 3H), 1 .39 (m, 1 H), 1 .20 (s, 3H ), 1 .12 (d, 3H), 1 .08
(s, 3H). (s, 3H).
No. 1.1 -180: Ethyl-1 -{2-[(1 -hydroxy-2.2,6-trimethylcyclohexyl)ethinyl]benzoyl}piperidin- 2-carboxylat No. 1.1-180: Ethyl 1 - {2 - [(1-hydroxy-2,2,6-trimethylcyclohexyl) ethynyl] benzoyl} piperidine-2-carboxylate
2-[(1-Hydroxy-2.2,6-trimethylcyclohexyl)ethinyl]benzoesäure (150 mg, 0.52 mmol), Hydroxy-1 H-benzotriazol (85 mg, 0.63 mmol) und 1 -Ethyl-3-(3- dimethylaminopropyl)carbodiimid-Hydrochlorid (120 mg, 0.63 mmol) wurden in Dichlormethan (7 ml) gelöst, 5 Minuten lang unter Argon gerührt und danach mit
Piperidincarbonsäureethylester (101 mg, 0.52 mmol) sowie Triethylamin (0.23 ml, 1 .67 mmol) versetzt. Das resultierende Reaktionsgemisch wurde 3 h lang bei einer 2 - [(1-Hydroxy-2,2,6-trimethylcyclohexyl) ethynyl] benzoic acid (150 mg, 0.52 mmol), hydroxy-1H-benzotriazole (85 mg, 0.63 mmol) and 1-ethyl-3- (3-dimethylaminopropyl) Carbodiimide hydrochloride (120 mg, 0.63 mmol) was dissolved in dichloromethane (7 ml), stirred under argon for 5 minutes and then washed with water Ethyl piperidinecarboxylate (101 mg, 0.52 mmol) and triethylamine (0.23 ml, 1.67 mmol) were added. The resulting reaction mixture was boiled for 3 h
Temperatur von 50 °C gerührt und nach dem Abkühlen auf Raumtemperatur mit Wasser versetzt. Die wässrige Phase wurde mehrfach mit Dichlormethan extrahiert. Die vereinigten organischen Phasen wurden über Magnesiumsulfat getrocknet, filtriert und unter vermindertem Druck eingeengt. Durch abschließende Stirred temperature of 50 ° C and after cooling to room temperature with water. The aqueous phase was extracted several times with dichloromethane. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. By final
säulenchromatographische Reinigung des erhaltenen Rohproduktes (unter column chromatographic purification of the resulting crude product (under
Verwendung eines Essigester/Heptan-Gradienten) wurde Ethyl-1 -{2-[(1-hydroxy-2.2,6- trimethylcyclohexyl)ethinyl]benzoyl}piperidin-2-carboxylat (148 mg, 66 % der Theorie) in Form eines farblosen Feststoffes isoliert. H-NMR (400 MHz, CDC δ, ppm) 7.48 (m, 1 H), 7.32 (m, 2H), 7.28 (m, 1 H), 5.57 / 5.50 (m, 1 H), 4.26 / 4.19 (q, 2H), 3.49 / 3.42 (m, 1 H), 3.32 / 3.12 (m, 1 H), 2.31 (m, 1 H), 1 .99 (m, 1 H), 1 .92 (m, 1 H), 1 .71 (m, 2H), 1 .64- 1 .48 (m, 4H), 1 .42-1 .27 (m, 8H), 1 .18 (s, 3H), 1 .08 / 0.97 (d, 3H), 1 .02 (s, 3H). No. 1.1 -260: Methyl-2-[(1-acetoxy-2.2,6-trimethylcyclohexyl)ethinyl]benzoat Using an ethyl acetate / heptane gradient) was added ethyl 1 - {2 - [(1-hydroxy-2,2,6-trimethylcyclohexyl) ethynyl] benzoyl} piperidine-2-carboxylate (148mg, 66% of theory) as a colorless Solid isolated. H-NMR (400 MHz, CDC δ, ppm) 7.48 (m, 1H), 7.32 (m, 2H), 7.28 (m, 1H), 5.57 / 5.50 (m, 1H), 4.26 / 4.19 (q , 2H), 3.49 / 3.42 (m, 1H), 3.32 / 3.12 (m, 1H), 2.31 (m, 1H), 1.99 (m, 1H), 1.92 (m, 1H ), 1 .71 (m, 2H), 1 .64- 1 .48 (m, 4H), 1 .42-1 .27 (m, 8H), 1 .18 (s, 3H), 1 .08 / 0.97 (d, 3H), 1 .02 (s, 3H). No. 1.1-260: methyl 2 - [(1-acetoxy-2,2,6-trimethylcyclohexyl) ethynyl] benzoate
Methyl-2-[(1 -hydroxy-2.2.6-trimethylcyclohexyl)ethinyl]benzoat (200 mg, 0.67 mmol) wurde in abs. Dichlormethan (5 ml) gelöst und mit Triethylamin (0.14 ml, 0.99 ml) sowie 4-Dimethylaminopyridin (8 mg, 0.07 mmol) versetzt. Nach 5 Minuten Rühren bei Raumtemperatur erfolgte die Zugabe von Acetylchlorid (68 mg, 0.87 mmol). Das resultierende Reaktionsgemisch wurde 4 h lang bei Raumtemperatur gerührt und danach mit Wasser und weiterem Dichlormethan versetzt. Die wässrige Phase wurde mehrfach mit Dichlormethan extrahiert. Die vereinigten organischen Phasen wurden über Magnesiumsulfat getrocknet, filtriert und unter vermindertem Druck eingeengt. Durch abschließende säulenchromatographische Reinigung des erhaltenen Methyl 2 - [(1-hydroxy-2,2,6-trimethylcyclohexyl) ethynyl] benzoate (200 mg, 0.67 mmol) was dissolved in abs. Dissolved dichloromethane (5 ml) and treated with triethylamine (0.14 ml, 0.99 ml) and 4-dimethylaminopyridine (8 mg, 0.07 mmol). After stirring for 5 minutes at room temperature, acetyl chloride (68 mg, 0.87 mmol) was added. The resulting reaction mixture was stirred for 4 hours at room temperature and then treated with water and further dichloromethane. The aqueous phase was extracted several times with dichloromethane. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. By final column chromatographic purification of the obtained
Rohproduktes (unter Verwendung eines Essigester/Heptan-Gradienten) wurde Methyl- 2-[(1-acetoxy-2,2,6-trimethylcyclohexyl)ethinyl]benzoat (57 mg, 25 % der Theorie) in Form eines farblosen, wachsartigen Feststoffes isoliert. H-NMR (400 MHz, CDCb δ,
ppm) 7.92 (d, 1 H), 7.63 (d, 1 H), 7.47 (dd. 1 H), 7.36 (dd, 1 H), 3.91 (s, 3H), 2.30 (s, 3H), 2.28 (m, 1 H), 1 .89 (m, 1 H). 1 .62 (m, 2H), 1 .51 (m, 2H), 1 .38 (m, 1 H), 1 .24 (s, 3H), 1 .1 1 (d, 3H), 1 .09 (s, 3H). No. L5-2: Ethyl-2-[(1 -hydroxy-2.2!6-trimethylcyclohexyl)ethinyl]cyclopent-1 -en-1 - carboxylat Crude product (using an ethyl acetate / heptane gradient), methyl 2 - [(1-acetoxy-2,2,6-trimethylcyclohexyl) ethynyl] benzoate (57 mg, 25% of theory) was isolated as a colorless, waxy solid , H-NMR (400 MHz, CDCb δ, 7.92 (d, 1H), 7.63 (d, 1H), 7.47 (dd, 1H), 7.36 (dd, 1H), 3.91 (s, 3H), 2.30 (s, 3H), 2.28 m, 1H), 1 .89 (m, 1H). 1 .62 (m, 2H), 1 .51 (m, 2H), 1 .38 (m, 1H), 1 .24 (s, 3H), 1 .1 1 (d, 3H), 1 .09 (s, 3H). No. L5-2: ethyl 2 - [(1-hydroxy-2.2 : 6-trimethylcyclohexyl) ethynyl] cyclopent-1-ene-1-carboxylate
Natriumhydrid (258 mg, 6.46 mmol, 60%ige Suspension) wurde in einem ausgeheizten Rundkolben mit abs. Diethylether (15 ml) unter Argon versetzt und nach 5 Minuten Rühren bei Raumtemperatur auf 0 °C eingekühlt. Danach erfolgte die Zugabe von Ethylcyclopentanon-2-carboxylat (800 mg, 4.97 mmol) und nach weiteren 10 min bei 0 °C wurde Trifluormethansulfonsäureanhydrid langsam zugetropft (1 .12 ml, 6.46 mmol). Das resultierende Reaktionsgemisch wurde 1 h lang bei 0 °C gerührt und danach mit ges. Ammoniumchloridlösung versetzt. Die wässrige Phase wurde mehrfach mit Diethylether extrahiert. Die vereinigten organischen Phasen wurden über Sodium hydride (258 mg, 6.46 mmol, 60% suspension) was dissolved in a heated round bottom flask with abs. Diethyl ether (15 ml) was added under argon and cooled after stirring for 5 minutes at room temperature to 0 ° C. Thereafter, the addition of ethylcyclopentanone-2-carboxylate (800 mg, 4.97 mmol) and after a further 10 min at 0 ° C trifluoromethanesulfonic anhydride was slowly added dropwise (1 .12 ml, 6.46 mmol). The resulting reaction mixture was stirred for 1 h at 0 ° C and then washed with sat. Ammonium chloride solution added. The aqueous phase was extracted several times with diethyl ether. The combined organic phases were over
Magnesiumsulfat getrocknet, filtriert und vorsichtig unter vermindertem Druck eingeengt. Durch abschließende saulenchromatographische Reinigung des erhaltenen Rohproduktes (unter Verwendung eines Essigester/Heptan-Gradienten) wurde Ethyl-2- {[(trifluormethyl)sulfonyl]oxy}cyclopent-1 -en-1 -carboxylat (680 mg, 47 % der Theorie) als farblose Flüssigkeit erhalten. Anschließend wurden Kupfer(l)iodid (34 mg, 0.18 mmol) und Bis(triphenylphosphin)palladium(ll)chlorid (95 mg, 0.14 mmol) unter Argon in einem ausgeheizten Rundkolben vorgelegt und mit abs. Toluol (3 ml) sowie einer Lösung von 1 -Ethinyl-2,2,6-trimethylcyclohexanol (150 mg, 0.90 mmol) in abs. Toluol (1 ml) und mit Diisopropylamin (0.25 ml, 1 .8 mmol) versetzt. Danach erfolgte die Zugabe einer Lösung von Ethyl-2-{[(trifluormethyl)sulfonyl]oxy}cyclopent-1 -en-1- carboxylat (260 mg, 0.90 mmol) in abs. Toluol (1 ml). Das resultierende Dried magnesium sulfate, filtered and concentrated under reduced pressure. Final purification by column of the crude product obtained (using an ethyl acetate / heptane gradient) gave ethyl 2- {[(trifluoromethyl) sulfonyl] oxy} cyclopent-1-ene-1-carboxylate (680 mg, 47% of theory) as obtained colorless liquid. Then copper (I) iodide (34 mg, 0.18 mmol) and bis (triphenylphosphine) palladium (II) chloride (95 mg, 0.14 mmol) were placed under argon in a heated round bottom flask and treated with abs. Toluene (3 ml) and a solution of 1-ethynyl-2,2,6-trimethylcyclohexanol (150 mg, 0.90 mmol) in abs. Toluene (1 ml) and diisopropylamine (0.25 ml, 1 .8 mmol). This was followed by the addition of a solution of ethyl 2 - {[(trifluoromethyl) sulfonyl] oxy} cyclopent-1-ene-1-carboxylate (260 mg, 0.90 mmol) in abs. Toluene (1 ml). The resulting
Reaktionsgemisch wurde 2 h lang bei Raumtemperatur gerührt und danach mit Wasser versetzt. Die wässrige Phase wurde mehrfach mit Dichlormethan extrahiert. Die vereinigten organischen Phasen wurden über Magnesiumsulfat getrocknet, filtriert und unter vermindertem Druck eingeengt. Durch abschließende
säulenchromatographische Reinigung des erhaltenen Rohproduktes (unter The reaction mixture was stirred for 2 hours at room temperature and then treated with water. The aqueous phase was extracted several times with dichloromethane. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. By final column chromatographic purification of the resulting crude product (under
Verwendung eines Essigester/Heptan-Gradienten) wurde Ethyl-2-[(1 -hydroxy-2,2,6- trimethylcyclohexyl)ethinyl]cyclopent-1 -en-1 -carboxylat (230 mg, 79 % der Theorie) in Form eines farblosen Öls isoliert. H-NMR (400 MHz, CDCh δ, ppm) 4.23 (q. 2H), 2.70 (m, 4H), 2.02 (s, 1 H), 1 .91 (m, 3H), 1 .63 (m, 2H), 1 .45 (m, 2H), 1 .35 (m, 1 H), 1 .30 (t, 3H), 1 .13 (s, 3H), 1 .08 (d, 3H), 1 .03 (s, 3H). Using an ethyl acetate / heptane gradient) was ethyl 2 - [(1-hydroxy-2,2,6-trimethylcyclohexyl) ethynyl] cyclopent-1-en-1-carboxylate (230 mg, 79% of theory) in the form of a isolated colorless oil. H-NMR (400 MHz, CDCh δ, ppm) 4.23 (q.2H), 2.70 (m, 4H), 2.02 (s, 1H), 1.91 (m, 3H), 1.63 (m, 2H ), 1 .45 (m, 2H), 1 .35 (m, 1H), 1 .30 (t, 3H), 1 .13 (s, 3H), 1 .08 (d, 3H), 1. 03 (s, 3H).
No. 1.13-1 16: Methyl-2-[(1 -hydroxy-2.6-dimethylcyclohexyl)ethinyl]benzoat No. 1.13-1 16: Methyl 2 - [(1-hydroxy-2,6-dimethylcyclohexyl) ethynyl] benzoate
2,6-Dimethylcyclohexanon (1500 mg, 1 1 .76 mmol) wurde in einem Rundkolben unter Argon in abs. Tetrahydrofuran (5 ml) gelöst und tropfenweise zu einer Lösung eines Lithiumacetylid-Ethylendiaminkomplexes (1760 mg, 15.29 mmol, 80% Gehalt) in abs. Tetrahydrofuran (10 ml) gegeben. Die Reaktionslösung wurde nach erfolgter Zugabe 2 h lang bei Raumtemperatur gerührt, anschließend mit Wasser versetzt und unter vermindertem Druck eingeengt. Der verbleibende Rückstand wurde mit Wasser und Dichlormethan versetzt und die wässrige Phase mehrfach mit Dichlormethan extrahiert. Die vereinigten organischen Phasen wurden über Magnesiumsulfat getrocknet, filtriert und unter vermindertem Druck eingeengt. Durch 2,6-Dimethylcyclohexanone (1500 mg, 1.176 mmol) was dissolved in a round bottom flask under argon in abs. Tetrahydrofuran (5 ml) was dissolved and added dropwise to a solution of a Lithiumacetylid-ethylenediamine complex (1760 mg, 15.29 mmol, 80% content) in abs. Tetrahydrofuran (10 ml) was added. The reaction solution was stirred for 2 h after the addition at room temperature, then treated with water and concentrated under reduced pressure. The remaining residue was mixed with water and dichloromethane and the aqueous phase extracted several times with dichloromethane. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. By
säulenchromatographische Reinigung des erhaltenen Rohproduktes (Gradient column-chromatographic purification of the crude product obtained (gradient
Essigester/Heptan) wurde 1 -Ethinyl-2.6-dimethylcyclohexanol (620 mg, 35 % der Theorie) als farbloser wachsartiger Feststoff isoliert. Anschließend wurden Ethyl acetate / heptane), 1-ethynyl-2,6-dimethylcyclohexanol (620 mg, 35% of theory) was isolated as a colorless waxy solid. Subsequently were
Kupfer(l)iodid (38 mg, 0.19 mmol) und Bis(triphenylphosphin)palladium(ll)chlorid (104 mg, 0.15 mmol) unter Argon in einem ausgeheizten Rundkolben vorgelegt und mit abs. Toluol (3 ml) sowie 2-lodbenzoesäuremethylester (258 mg, 0.99 mmol) versetzt. Nach 10 Min Rühren bei Raumtemperatur erfolgte die tropfenweise Zugabe einer Lösung von 1 -Ethinyl-2,6-dimethylcyclohexanol (150 mg, 0.99 mmol) in abs. Toluol (1 ml) und von Diisopropylamin (0.28 ml, 1 .97 mmol). Das resultierende orangefarbene Copper (I) iodide (38 mg, 0.19 mmol) and bis (triphenylphosphine) palladium (II) chloride (104 mg, 0.15 mmol) under argon in a heated round bottom flask and charged with abs. Toluene (3 ml) and methyl 2-iodobenzoate (258 mg, 0.99 mmol) were added. After 10 min stirring at room temperature, the dropwise addition of a solution of 1-ethynyl-2,6-dimethylcyclohexanol (150 mg, 0.99 mmol) in abs. Toluene (1 mL) and diisopropylamine (0.28 mL, 1.97 mmol). The resulting orange
Reaktionsgemisch wurde 4 h lang bei Raumtemperatur gerührt und danach mitThe reaction mixture was stirred for 4 h at room temperature and then with
Wasser versetzt. Die wässrige Phase wurde mehrfach mit Dichlormethan extrahiert.
Die vereinigten organischen Phasen wurden über Magnesiumsulfat getrocknet, filtriert und unter vermindertem Druck eingeengt. Durch abschließende Water is added. The aqueous phase was extracted several times with dichloromethane. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. By final
säulenchromatographische Reinigung des erhaltenen Rohproduktes (unter column chromatographic purification of the resulting crude product (under
Verwendung eines Essigester/Heptan-Gradienten) konnte das gewünschte Using an ethyl acetate / heptane gradient) could achieve the desired
Reaktionsprodukt Methyl-2-[(1 -hydroxy-2,6-dimethylcyclohexyl)ethinyl]benzoat als Diastereomerengemisch erhalten werden (170 mg, 57 % der Theorie) und danach die beiden Diastereomere durch eine erneute säulenchromatographische Trennung getrennt werden. Auf diese Weise konnten Methyl-2-{[(1 S,2R,6S)-1 -hydroxy-2,6- dimethylcyclohexyl]ethinyl}benzoat (Diastereomer 1 , 71 mg), H-NMR (400 MHz, CDCh 6, ppm) 7.91 (d, 1 H), 7.52 (d, 1 H), 7.44 (t, 1 H), 7.35 (t, 1 H), 3.90 (s, 3H), 1 .78 (m. 1 H), 1 .68 (m, 2H), 1 .49 (m, 2H), 1 .38 (m, 2H), 1 .19 (d, 6H), 1 .10 (m, 2H) und Methyl-2-{[(1 R,2R,6S)-1 -hydroxy-2,6-dimethylcyclohexyl]ethinyl}benzoat Reaction product methyl-2 - [(1-hydroxy-2,6-dimethylcyclohexyl) ethynyl] benzoate are obtained as a mixture of diastereomers (170 mg, 57% of theory) and then the two diastereomers are separated by a new column chromatographic separation. In this way, methyl 2 - {[(1S, 2R, 6S) -1-hydroxy-2,6-dimethylcyclohexyl] ethynyl} benzoate (diastereomer 1, 71 mg), H-NMR (400 MHz, CDCh 6, ppm) 7.91 (d, 1H), 7.52 (d, 1H), 7.44 (t, 1H), 7.35 (t, 1H), 3.90 (s, 3H), 1.78 (m.1 H) , 1 .68 (m, 2H), 1 .49 (m, 2H), 1 .38 (m, 2H), 1 .19 (d, 6H), 1 .10 (m, 2H) and methyl-2 {[(1R, 2R, 6S) -1-hydroxy-2,6-dimethylcyclohexyl] ethynyl} benzoate
(Diastereomer 2, 99 mg), 1H-NMR (400 MHz, CDCh δ, ppm) 7.91 (d, 1 H), 7.54 (d, 1 H), 7.44 (t, 1 H), 7.35 (t, 1 H), 3.90 (s, 3H), 2.39 (s, 1 H), 1 .65 (m, 4H), 1 .50-1 .25 (m, 2H), 1 .16 (d, 6H), 1 .1 1 -1 .00 (m, 2H) isoliert werden. (Diastereomer 2, 99 mg), 1 H NMR (400 MHz, CDCh δ, ppm) 7.91 (d, 1H), 7.54 (d, 1H), 7.44 (t, 1H), 7.35 (t, 1 H), 3.90 (s, 3H), 2.39 (s, 1H), 1 .65 (m, 4H), 1 .50-1 .25 (m, 2H), 1 .16 (d, 6H), 1 .1 1 -1 .00 (m, 2H) can be isolated.
In Analogie zu oben angeführten und in den nachstehenden Tabellen rezitierten In analogy to the above and recited in the tables below
Herstellungsbeispielen und unter Berücksichtigung der allgemeinen Angaben zur Herstellung von substituierten l -(Arylethinyl)-, 1 -(Heteroarylethinyl)-, 1 - (Heterocyciylethinyl)- und 1-(Cyloalkenylethinyl)-cyclohexanolen sowie deren Analoga der allgemeinen Formel (I) erhält man folgende in den Tabellen 1 bis 34 spezifisch genannten Verbindungen:
Preparation examples and taking into account the general information on the preparation of substituted L - (arylethynyl) -, 1 - (heteroarylethynyl) -, 1 - (Heterocyciylethinyl) - and 1- (cycloalkenylethynyl) cyclohexanols and their analogs of the general formula (I) the following compounds mentioned specifically in Tables 1 to 34:
Tabelle 1:Table 1:
Tabelle 2: Table 2:
No. R5 R6 A A2 A3 A4 No. R 5 R 6 AA 2 A 3 A 4
1.2-1 OH F N C-H C-H C-H1.2-1 OH F N C-H C-H C-H
I.2-2 OH Cl N C-H C-H C-HI.2-2 OH Cl N C-H C-H C-H
I.2-3 OH Br N C-H C-H C-HI.2-3 OH Br N C-H C-H C-H
I.2-4 OH I N C-H C-H C-HI.2-4 OH I N C-H C-H C-H
I.2-5 OH CH3 N C-H C-H C-HI.2-5 OH CH 3 CH CH CH
I.2-6 OH OCH3 N C-H C-H C-HI.2-6 OH OCH 3 N CH CH CH
I.2-7 OH SCH3 N C-H C-H C-HI.2-7 OH SCH 3 N CH CH CH
I.2-8 OH CF3 N C-H C-H C-HI.2-8 OH CF 3 N CH CH CH
I.2-9 OH OCF3 N C-H C-H C-HI.2-9 OH OCF3 N C-H C-H C-H
1.2-10 OH SCF3 N C-H C-H C-H1.2-10 OH SCF 3 N CH CH CH
1.2-1 1 OH NH2 N C-H C-H C-H1.2-1 1 OH NH 2 N CH CH CH
1.2-12 OH N02 N C-H C-H C-H1.2-12 OH N0 2 N CH CH CH
1.2-13 OH CN N C-H C-H C-H 1.2-13 OH CN N C-H C-H C-H
1.2-14 OH N C-H C-H C-H 1.2-14 OH N C-H C-H C-H
0^0-" 0 ^ 0- "
1.2-15 OH N C-H C-H C-H 1.2-15 OH N C-H C-H C-H
1.2-16 OH F C-H N C-H C-H
Tabelle 3: 1.2-16 OH F CH N CH CH Table 3:
No. R5 R6 A5 R" R12No. R 5 R 6 A 5 R " R 12
1.3-1 OH CH3 S H H 1.3-1 OH CH 3 SHH
I.3-2 OH S H H I.3-2 OH S H H
I.3-3 OH S H H I.3-3 OH S H H
I.3-4 OH s H HI.3-4 OH s H H
O^H O ^ H
I.3-5 OH s H H I.3-5 OH s H H
I.3-6 OH s H HI.3-6 OH s H H
OH OH
I.3-7 OH HI.3-7 OH H
I s H I s H
/° / °
I.3-8 OH s H HI.3-8 OH s H H
I I
I.3-9 OH s CH3 H o^o^ I.3-9 OH s CH 3 H o ^ o ^
1.3-10 OH s CH3 CH3 o^o"" 1.3-10 OH s CH 3 CH 3 o ^ o ""
1.3-1 1 OH s H CH3 o^o""
Tabelle 4: 1.3-1 1 OH s H CH 3 o ^ o "" Table 4:
No. R5 R6 A6 A7 R13 R14 R17 R18 No. R 5 R 6 A 6 A 7 R 13 R 14 R 17 R 18
1.4-1 OH CH2 CH2 H H H H 1.4-1 OH CH 2 CH 2 HHHH
I.4-2 OH CH2 CH2 H H H H I.4-2 OH CH 2 CH 2 HHHH
I.4-3 OH CH2 0 H H H H I.4-3 OH CH 2 0 HHHH
I.4-4 OH CH2 0 H H H H I.4-4 OH CH 2 0 HHHH
I.4-5 OH CH2 s H H H H I.4-5 OH CH 2 s HHHH
I.4-6 OH CH2 s H H H H I.4-6 OH CH 2 s HHHH
I.4-7 OH CH2 H H H H I.4-7 OH CH 2 HHHH
I.4-8 OH CH2 H H H H I.4-8 OH CH 2 HHHH
I.4-9 OH X CH2 CH2 H H H H I.4-9 OH X CH 2 CH 2 HHHH
e OH e OH
1.4-10 OH CH2 CH2 H H H H 1.4-10 OH CH 2 CH 2 HHHH
1.4-1 1 OH CH2 CH2 H H H H 1.4-1 1 OH CH 2 CH 2 HHHH
1.4-12 OH CH2 CH2 H H H H
1.4-12 OH CH 2 CH 2 HHHH
Tabelle 5: Table 5:
No. R5 R6 A8 R19 R20 R22 R23 No. R 5 R 6 A 8 R 19 R 20 R 22 R 23
1.5-1 OH CH2 H H H H o^o"" 1.5-1 OH CH 2 HHHH o ^ o ""
I.5-2 OH CH2 H H H H I.5-2 OH CH 2 HHHH
I.5-3 OH 0 H H H H o^-o-^ I.5-3 OH 0 H H H H o ^ -o ^
I.5-4 OH 0 H H H H
I.5-4 OH 0 HHHH
Tabelle 6: Table 6:
No. R5 R6 A9 R25 R26 R28 R29 No. R 5 R 6 A 9 R 25 R 26 R 28 R 29
1.6-13 OAc CH2 H H H H1.6-13 OAc CH 2 HHHH
1.6-14 OAc CH2 H H H H1.6-14 OAc CH 2 HHHH
1.6-15 OSiEi3 CH2 H H H H1.6-15 OSiEi 3 CH 2 HHHH
1.6-16 OSiEia CH2 H H H H 1.6-16 OSiEia CH 2 HHHH
Tabelle 7: Table 7:
No. R5 R6 A1 A2 A3 A4 No. R 5 R 6 A 1 A 2 A 3 A 4
1.8-1 OH F N C-H C-H C-H1.8-1 OH F N C-H C-H C-H
I.8-2 OH Cl N C-H C-H C-HI.8-2 OH Cl N C-H C-H C-H
I.8-3 OH Br N C-H C-H C-HI.8-3 OH Br N C-H C-H C-H
I.8-4 OH I N C-H C-H C-H
No. R5 R6 A5 R" R12I.8-4 OH IN CH CH CH No. R 5 R 6 A 5 R " R 12
1.9-21 OH N-CH3 CH3 H 1.9-21 OH N-CH 3 CH 3 H
I.9-22 OH N-CH3 H CH3 I.9-22 OH N-CH3 H CH3
I.9-23 OSi(Et)3 S H H I.9-23 OSi (Et) 3 SHH
I.9-24 OSiMe2t-Bu s H H I.9-24 OSiMe 2 t-Bu s HH
I.9-25 OAc s H H I.9-25 OAc s H H
Tabelle 10:
Table 10:
No. R5 R6 A6 A7 R13 R14 R17 R18No. R 5 R6 A 6 A 7 R 13 R 14 R 17 R 18
1.10-1 OH CH2 CH2 H H H H 1.10-1 OH CH 2 CH 2 HHHH
1.10-2 OH CH2 CH2 H H H H 1.10-2 OH CH 2 CH 2 HHHH
1.10-3 OH CH2 0 H H H H 1.10-3 OH CH 2 0 HHHH
1.10-4 OH CH2 0 H H H H 1.10-4 OH CH 2 0 HHHH
1.10-5 OH CH2 s H H H H
1.10-5 OH CH 2 s HHHH
No. R5 R6 A8 R9 R20 R22 R23 No. R 5 R 6 A 8 R 9 R 20 R22 R 23
1.11-13 OAc CH2 H H H H1.11-13 OAc CH 2 HHHH
1.11-14 OAc CH2 H H H H1.11-14 OAc CH 2 HHHH
1.11-15 OSiEi3 CH2 H H H H1.11-15 OSiEi 3 CH 2 HHHH
1.11-16 OSiEt3 CH2 H H H H 1.11-16 OSiEt 3 CH 2 HHHH
Tabelle 12: Table 12:
No. R5 R6 A9 R25 R26 R28 R29 No. R 5 R 6 A 9 R 25 R 26 R 28 R 29
1.12-1 OH CH2 H H H H 1.12-1 OH CH 2 HHHH
1.12-2 OH CH2 H H H H 1.12-2 OH CH 2 HHHH
1.12-3 OH 0 H H H H 1.12-3 OH 0 H H H H
1.12-4 OH 0 H H H H 1.12-4 OH 0 H H H H
1.12-5 OH s H H H H
1.12-5 OH s HHHH
Tabelle 13:Table 13:
Tabelle 14: Table 14:
No. R5 R6 A5 R11 R12No. R 5 R 6 A 5 R 11 R 12
1.15-1 OH CH3 S H H 1.15-1 OH CH 3 SHH
1.15-2 OH s H H
1.15-2 OH s HH
Tabelle 16: Table 16:
No. R5 R6 A6 A7 R13 R14 R17 R18 No. R 5 R 6 A 6 A 7 R 13 R 14 R 17 R 18
1.16-1 OH CH2 CH2 H H H H o^o"" 1.16-1OH CH 2 CH 2 HHHH o ^ o ""
1.16-2 OH CH2 CH2 H H H H
No. R5 R6 A6 A7 R13 R14 R7 R8 1.16-2 OH CH 2 CH 2 HHHH No. R5 R 6 A 6 A 7 R 13 R 14 R 7 R 8
1.16-18 OSiEt3 Q Q^ CH2 CH2 H H H H1.16-18 OSiEt 3 QQ ^ CH 2 CH 2 HHHH
Tabelle 17:Table 17:
Tabelle 18:
Table 18:
5
Tabelle 19:5 Table 19:
Tabelle 21: Table 21:
Tabelle 22:
Table 22:
No. R5 R6 A5 R" R12No. R 5 R 6 A 5 R " R 12
1.22-1 OH S H H 1.22-1 OH S H H
I.22-2 OH S H H I.22-2 OH S H H
I.22-3 OH S H HI.22-3 OH S H H
O^H O ^ H
I.22-4 OH S H H I.22-4 OH S H H
I.22-5 OH S CH3 H I.22-5 OH S CH 3 H
I.22-6 OH s CH3 CH3 I.22-6 OH s CH 3 CH 3
I.22-7 OH s H CH3
I.22-7 OH s H CH 3
Tabelle 25: Table 25:
No. R5 R6 A5 R11 R12 No. R 5 R 6 A 5 R 11 R 12
1.26-1 OH S H H 1.26-1 OH S H H
I.26-2 OH s H H I.26-2 OH s H H
I.26-3 OH s H H I.26-3 OH s H H
I.26-4 OH s H H I.26-4 OH s H H
I.26-5 OH s CH3 H I.26-5 OH s CH 3 H
I.26-6 OH s CH3 CH3 I.26-6 OH s CH 3 CH 3
I.26-7 OH s H CH3
Tabelle 27:I.26-7 OH s H CH 3 Table 27:
Tabelle 29: Table 29:
Tabelle 30:
Table 30:
No. R5 R6 A5 R" R12No. R 5 R 6 A 5 R " R 12
1.30-1 OH S H H1.30-1 OH S H H
I.30-2 OH S H HI.30-2 OH S H H
I.30-3 OH s H HI.30-3 OH s H H
I.30-4 OH s H HI.30-4 OH s H H
I.30-5 OH s CH3 HI.30-5 OH s CH 3 H
I.30-6 OH s CH3 CH3 I.30-6 OH s CH 3 CH 3
I.30-7 OH s H CH3
I.30-7 OH s H CH 3
Tabelle 31:Table 31:
Tabelle 32: Table 32:
Tabelle 33:Table 33:
Tabelle 34: Table 34:
Spektroskopische Daten ausgewählter Tabellenbeispiele: Spectroscopic data of selected table examples:
Beispiel No.1.1-1 : Example No.1.1-1:
1H-NMR (400 MHz, CHC ) δ 7.43 (m, 1 H), 7.23 (m, 1 H), 7.09 (m, 2H), 1.99 (br. s, 1 H, 1 H-NMR (400 MHz, CHC) δ 7.43 (m, 1H), 7.23 (m, 1H), 7.09 (m, 2H), 1.99 (br. S, 1H,
OH), 1.97 (m, 1 H), 1.72 (m, 1 H), 1.63 (m, 1 H), 1.52 (m, 1 H), 1.48 (m, 2H), 1.39 (m, 1H), 1.20 (s.3H), 1.13 (d,3H), 1.06 (s.3H).
Beispiel No.1.1-53: OH), 1.97 (m, 1H), 1.72 (m, 1H), 1.63 (m, 1H), 1.52 (m, 1H), 1.48 (m, 2H), 1.39 (m, 1H), 1.20 (s.3H), 1.13 (d, 3H), 1.06 (s.3H). Example No.1.1-53:
H-NMR (400 MHz, CHCb) δ 7.43 (d, 1H), 7.19 (m, 2H), 7.13 (m, 1H), 2.46 (s, 3H), 1.97 (m, 1 H), 1.94 (br. s, 1 H, OH), 1.71 (m, 1 H), 1.62 (m, 1 H), 1.53 (m, 1 H), 1.47 (m, H-NMR (400 MHz, CHCb) δ 7.43 (d, 1H), 7.19 (m, 2H), 7.13 (m, 1H), 2.46 (s, 3H), 1.97 (m, 1H), 1.94 (br. s, 1H, OH), 1.71 (m, 1H), 1.62 (m, 1H), 1.53 (m, 1H), 1.47 (m,
2H), 1.39 (m, 1H), 1.21 (s, 3H), 1.13 (d, 3H), 1.06 (s, 3H). 2H), 1.39 (m, 1H), 1.21 (s, 3H), 1.13 (d, 3H), 1.06 (s, 3H).
Beispiel No.1.1-56: Example No.1.1-56:
1H-NMR (400 MHz, CHCb) δ 7.67 (d, 1 H), 7.62 (m, 1 H), 7.50 (m, 1 H), 7.41 (m, 1 H), 2.00 (br. s, 1 H, OH), 1.97 (m, 1 H), 1.72 (m, 1 H), 1.62 (m, 1 H), 1.51 (m, 1 H), 1.49 (m, 2H), 1.39 (m, 1H), 1.21 (s, 3H), 1.12 (d, 3H), 1.07 (s, 3H). 1 H-NMR (400 MHz, CHCb) δ 7.67 (d, 1H), 7.62 (m, 1H), 7.50 (m, 1H), 7.41 (m, 1H), 2.00 (br. S, 1 H, OH), 1.97 (m, 1H), 1.72 (m, 1H), 1.62 (m, 1H), 1.51 (m, 1H), 1.49 (m, 2H), 1.39 (m, 1H) , 1.21 (s, 3H), 1.12 (d, 3H), 1.07 (s, 3H).
Beispiel No.1.1-57: Example No.1.1-57:
H-NMR (400 MHz, CHCb) δ 7.52 (d, 1 H), 7.32 (m, 1 H), 7.22 (m, 2H), 1.97 (br. s, 1 H, OH), 1.92 (m, 1H), 1.68-1.58 (m, 2H), 1.51 (m, 1H), 1.46 (m, 2H), 1.37 (m, 1H), 1.18 (s, 3H), 1.10 (d, 3H), 1.06 (s, 3H). H-NMR (400 MHz, CHCb) δ 7.52 (d, 1H), 7.32 (m, 1H), 7.22 (m, 2H), 1.97 (br, s, 1H, OH), 1.92 (m, 1H ), 1.68-1.58 (m, 2H), 1.51 (m, 1H), 1.46 (m, 2H), 1.37 (m, 1H), 1.18 (s, 3H), 1.10 (d, 3H), 1.06 (s, 3H).
Beispiel No.1.1-66: Example No.1.1-66:
1H-NMR (400 MHz, CHCb) d 7.44 (d, 1 H), 7.22 (m, 2H), 7.12 (m, 1H), 2.82 (q, 2H), 1.97 (m, 1 H), 1.95 (br. s, 1 H, OH), 1.70 (m, 1 H), 1.62 (m, 1 H), 1.54 (m, 1 H), 1.48 (m, 2H), 1.40 (m, 1H), 1.24 (t, 3H), 1.20 (s, 3H), 1.13 (d, 3H), 1.07 (s, 3H). 1 H-NMR (400 MHz, CHCb) d 7.44 (d, 1H), 7.22 (m, 2H), 7.12 (m, 1H), 2.82 (q, 2H), 1.97 (m, 1H), 1.95 ( s, 1H, OH), 1.70 (m, 1H), 1.62 (m, 1H), 1.54 (m, 1H), 1.48 (m, 2H), 1.40 (m, 1H), 1.24 ( t, 3H), 1.20 (s, 3H), 1.13 (d, 3H), 1.07 (s, 3H).
Beispiel No.1.1-67: Example No.1.1-67:
1H-NMR (400 MHz, CHCb) d 7.44 (d, 1H), 7.29 (m, 2H), 7.13 (m, 1H), 3.48 (sept, 1H), 1.99 (m, 1 H), 1.97 (br. s, 1 H, OH), 1.71-1.59 (m, 2H), 1.54 (m, 1 H), 1.49-1.37 (m, 3H), 1.26 (d, 3H), 1.19 (s, 3H), 1.12 (d, 3H), 1.06 (s, 3H). 1 H-NMR (400 MHz, CHCb) d 7.44 (d, 1H), 7.29 (m, 2H), 7.13 (m, 1H), 3.48 (sept, 1H), 1.99 (m, 1H), 1.97 (br s, 1H, OH), 1.71-1.59 (m, 2H), 1.54 (m, 1H), 1.49-1.37 (m, 3H), 1.26 (d, 3H), 1.19 (s, 3H), 1.12 (d, 3H), 1.06 (s, 3H).
Beispiel No.1.1-70:Example No.1.1-70:
H-NMR (400 MHz, CHCb) δ 7.49 (m, 1H), 7.31 (m, 1H), 7.18 (m, 2H), 6.73-6.38 (t, 1 H), 1.99 (br. s, 1 H, OH), 1.95 (m, 1 H), 1.70 (m, 1 H), 1.62 (m, 1 H), 1.50 (m, 1 H), 1.47 (m, 2H), 1.39 (m, 1 H), 1.19 (s, 3H), 1.11 (d, 3H), 1.07 (s, 3H).
Beispiel No.1.1-71: H-NMR (400 MHz, CHCb) δ 7.49 (m, 1H), 7.31 (m, 1H), 7.18 (m, 2H), 6.73-6.38 (t, 1H), 1.99 (br. S, 1H, OH), 1.95 (m, 1H), 1.70 (m, 1H), 1.62 (m, 1H), 1.50 (m, 1H), 1.47 (m, 2H), 1.39 (m, 1H), 1.19 (s, 3H), 1.11 (d, 3H), 1.07 (s, 3H). Example No.1.1-71:
H-NMR (400 MHz, CHCb) δ 10.57 (s, 1H), 7.94 (m, 1H), 7.56 (m, 2H), 7.44 (m, 1H), 2.04 (br. s, 1H, OH), 2.00 (m, 1H), 1.68 (m, 2H), 1.53 (m, 1H), 1.49 (m, 2H), 1.41 (m, 1H), 1.21 (s, 3H), 1.13 (d, 3H), 1.07 (s, 3H). H NMR (400 MHz, CHCb) δ 10.57 (s, 1H), 7.94 (m, 1H), 7.56 (m, 2H), 7.44 (m, 1H), 2.04 (br, s, 1H, OH), 2.00 (m, 1H), 1.68 (m, 2H), 1.53 (m, 1H), 1.49 (m, 2H), 1.41 (m, 1H), 1.21 (s, 3H), 1.13 (d, 3H), 1.07 ( s, 3H).
Beispiel No.1.1-74: Example No.1.1-74:
1 H-NMR (400 MHz, CHCb) 67.50 (m, 1H), 7.36-7.27 (m, 3H), 3.90 (s, 2H), 2.06 (br. s, 1H, OH), 2.00 (m, 1H), 1.67 (m, 2H), 1.50 (m, 2H), 1.40 (m, 2H), 1.20 (s, 3H), 1.13 (d, 3H), 1.07 (s, 3H). 1 H-NMR (400 MHz, CHCb) 67.50 (m, 1H), 7.36-7.27 (m, 3H), 3.90 (s, 2H), 2.06 (br, s, 1H, OH), 2.00 (m, 1H) , 1.67 (m, 2H), 1.50 (m, 2H), 1.40 (m, 2H), 1.20 (s, 3H), 1.13 (d, 3H), 1.07 (s, 3H).
Beispiel No.1.1-75: Example No.1.1-75:
1H-NMR (400 MHz, CHCb) δ 8.40 (s, 1 H), 7.85 (m, 1 H), 7.76 (m, 1 H), 7.58 (br. s, 1 H, OH), 7.06 (m, 1H), 1.89 (m, 1H), 1.78 (br. s.1H, OH), 1.62 (m, 2H).1.48 (m, 2H), 1.36 (m, 2H), 1.12 (s, 3H), 1.05 (d, 3H), 1.01 (s, 3H). 1 H-NMR (400 MHz, CHCb) δ 8.40 (s, 1H), 7.85 (m, 1H), 7.76 (m, 1H), 7.58 (br. S, 1H, OH), 7.06 (m , 1H), 1.89 (m, 1H), 1.78 (br. S.1H, OH), 1.62 (m, 2H) .1.48 (m, 2H), 1.36 (m, 2H), 1.12 (s, 3H), 1.05 (d, 3H), 1.01 (s, 3H).
Beispiel No.1.1-77:Example No.1.1-77:
H-NMR (400 MHz, CHCb) δ 8.56 (s, 1 H), 7.88 (m, 1 H), 7.47 (m, 1 H), 7.29 (m, 2H), 4.23 (q, 2H), 1.99 (br. s, 1H, OH), 1.97 (m, 1H), 1.67 (m, 2H), 1.56 (m, 1H), 1.48 (m, 2H), 1.39 (m, 1H), 1.21 (s, 3H), 1.13 (d, 3H), 1.06 (s, 3H). H-NMR (400 MHz, CHCb) δ 8.56 (s, 1H), 7.88 (m, 1H), 7.47 (m, 1H), 7.29 (m, 2H), 4.23 (q, 2H), 1.99 ( br. s, 1H, OH), 1.97 (m, 1H), 1.67 (m, 2H), 1.56 (m, 1H), 1.48 (m, 2H), 1.39 (m, 1H), 1.21 (s, 3H) , 1.13 (d, 3H), 1.06 (s, 3H).
Beispiel No.1.1-79:Example No.1.1-79:
H-NMR (400 MHz, CHCb) δ 7.51 (m, 1H).7.34 (m, 1H), 7.19 (m, 1H), 7.09 (m, 1H), 2.32 (s, 3H), 1.97 (br. s, 1 H, OH), 1.95 (m, 1 H), 1.63 (m, 2H), 1.50 (m, 1 H), 1.47 (m, 1H), 1.39 (m, 2H), 1.19 (s, 3H), 1.10 (d, 3H), 1.06 (s.3H). H-NMR (400 MHz, CHCb) δ 7.51 (m, 1H) .7.34 (m, 1H), 7.19 (m, 1H), 7.09 (m, 1H), 2.32 (s, 3H), 1.97 (br , 1 H, OH), 1.95 (m, 1H), 1.63 (m, 2H), 1.50 (m, 1H), 1.47 (m, 1H), 1.39 (m, 2H), 1.19 (s, 3H) , 1.10 (d, 3H), 1.06 (s.3H).
Beispiel No.1.1-87: Example No.1.1-87:
1H-NMR (400 MHz, CHCb) δ 8.09 (m, 1 H), 7.37 (m, 2H), 7.30 (m, 1 H), 6.96 (m, 1 H), 2.00 (br. s, 1 H, OH), 1.98 (m, 1 H), 1.68 (m, 2H), 1.54 (m, 1 H), 1.49 (s, 9H), 1.48 (m, 1H), 1.41 (m, 2H), 1.21 (s, 3H), 1.13 (d, 3H), 1.08 (s, 3H).
Beispiel No.1.1-88: 1 H-NMR (400 MHz, CHCb) δ 8.09 (m, 1H), 7.37 (m, 2H), 7.30 (m, 1H), 6.96 (m, 1H), 2.00 (br. S, 1H , OH), 1.98 (m, 1H), 1.68 (m, 2H), 1.54 (m, 1H), 1.49 (s, 9H), 1.48 (m, 1H), 1.41 (m, 2H), 1.21 ( s, 3H), 1.13 (d, 3H), 1.08 (s, 3H). Example No.1.1-88:
H-NMR (400 MHz, CHC ) δ 7.59 (m, 1 H), 7.46 (m, 1 H), 7.36 (m, 1 H), 7.12 (m, 1 H), 6.99 (br. s, 1H, NH), 3.01 (s, 3H), 2.01 (br. s, 1H, OH), 1.98 (m, 1H), 1.70 (m, 1H), 1.59 (m, 1 H), 1.52 (m, 2H), 1.47 (m, 1 H), 1.34 (m, 1 H), 1.20 (s, 3H), 1.12 (d, 3H), 1.07 (s, 3H). H NMR (400 MHz, CHC) δ 7.59 (m, 1H), 7.46 (m, 1H), 7.36 (m, 1H), 7.12 (m, 1H), 6.99 (br. S, 1H, NH), 3.01 (s, 3H), 2.01 (br s, 1H, OH), 1.98 (m, 1H), 1.70 (m, 1H), 1.59 (m, 1H), 1.52 (m, 2H), 1.47 (m, 1H), 1.34 (m, 1H), 1.20 (s, 3H), 1.12 (d, 3H), 1.07 (s, 3H).
Beispiel No.1.1-91:Example No.1.1-91:
H-NMR (400 MHz, CHCb) δ 7.61 (m, 1H).7.55 (m, 1H), 7.36 (m, 1H), 7.13 (m, 1H), 7.01 (br. s, 2H, NH), 2.04 (br. s, 1H, OH), 2.00 (m, 1H), 1.70 (m, 1H), 1.59 (m, 1H), 1.51 (m, 2H), 1.47 (m, 1H), 1.30 (m, 1H), 1.21 (s, 3H), 1.13 (d, 3H), 1.07 (s, 3H). H NMR (400 MHz, CHCb) δ 7.61 (m, 1H) .7.55 (m, 1H), 7.36 (m, 1H), 7.13 (m, 1H), 7.01 (br. S, 2H, NH), 2.04 (brs s, 1H, OH), 2.00 (m, 1H), 1.70 (m, 1H), 1.59 (m, 1H), 1.51 (m, 2H), 1.47 (m, 1H), 1.30 (m, 1H ), 1.21 (s, 3H), 1.13 (d, 3H), 1.07 (s, 3H).
Beispiel No.1.1-92:Example No.1.1-92:
H-NMR (400 MHz, CHCb) δ 7.62 (m, 1 H), 7.56 (m, 1 H), 7.38 (m, 1 H), 7.11 (m, 1 H), 7.00 (br. s, 1H, NH), 3.05 (s, 3H), 2.03 (br. s, 1H, OH), 2.00 (m, 1H), 1.72 (m, 1H), 1.60 (m, 1H), 1.50 (m, 2H), 1.45 (m, 1H), 1.28 (m, 1H).1.20 (s.3H), 1.13 (d, 3H), 1.08 (s, 3H). H-NMR (400 MHz, CHCb) δ 7.62 (m, 1H), 7.56 (m, 1H), 7.38 (m, 1H), 7.11 (m, 1H), 7.00 (br. S, 1H, NH), 3.05 (s, 3H), 2.03 (brs s, 1H, OH), 2.00 (m, 1H), 1.72 (m, 1H), 1.60 (m, 1H), 1.50 (m, 2H), 1.45 (m, 1H), 1.28 (m, 1H) .1.20 (s.3H), 1.13 (d, 3H), 1.08 (s, 3H).
Beispiel No.1.1-97:Example No.1.1-97:
H-NMR (400 MHz, CDCb δ, ppm) 7.48-7.40 (m, 3H), 7.39-7.28 (m, 4H), 6.92 (m, 2H), 5.10 (s, 3H), 1.93 (m, 2H), 1.65 (m, 1H), 1.49-1.39 (m, 2H), 1.33 (m, 1H), 1.322 (m, 1H).1.12 (s, 3H), 1.04 (d, 3H), 1.01 (s, 3H). H NMR (400 MHz, CDCbδ, ppm) 7.48-7.40 (m, 3H), 7.39-7.28 (m, 4H), 6.92 (m, 2H), 5.10 (s, 3H), 1.93 (m, 2H) , 1.65 (m, 1H), 1.49-1.39 (m, 2H), 1.33 (m, 1H), 1.322 (m, 1H) .1.12 (s, 3H), 1.04 (d, 3H), 1.01 (s, 3H ).
Beispiel No.1.1-99:Example No.1.1-99:
H-NMR (400 MHz, CHCb) δ 7.54 (m, 1H), 7.43 (m, 1H), 7.32 (m, 1H), 7.16 (m, 1H), 7.10 (m, 1H), 6.94 (d, 1H), 6.66 (d, 1H), 1.92 (br. s, 1H, OH), 1.89 (m, 1H), 1.61 (m, 1H), 1.49-1.42 (m, 3H), 1.32 (m, 1H), 1.12 (s, 3H), 1.01 (s, 3H), 0.98 (s, 3H). H-NMR (400 MHz, CHCb) δ 7.54 (m, 1H), 7.43 (m, 1H), 7.32 (m, 1H), 7.16 (m, 1H), 7.10 (m, 1H), 6.94 (d, 1H ), 6.66 (d, 1H), 1.92 (brs s, 1H, OH), 1.89 (m, 1H), 1.61 (m, 1H), 1.49-1.42 (m, 3H), 1.32 (m, 1H), 1.12 (s, 3H), 1.01 (s, 3H), 0.98 (s, 3H).
Beispiel No.1.1-123: Example No.1.1-123:
H-NMR (400 MHz, CDCb δ, ppm) 7.72 (s, 1 H), 7.43 (d, 1 H), 7.37 (m, 1 H), 3.90 (s, 3H), 2.38 (s, 3H), 1.95 (m, 1 H), 1.72 (m, 1 H), 1.61 (m, 3H), 1.47 (m, 2H), 1.38 (m, 1 H), 1.20 (s, 3H), 1.12 (d, 3H), 1.06 (s, 3H).
Beispiel No.1.1-125: H-NMR (400 MHz, CDCb δ, ppm) 7.72 (s, 1H), 7.43 (d, 1H), 7.37 (m, 1H), 3.90 (s, 3H), 2.38 (s, 3H), 1.95 (m, 1H), 1.72 (m, 1H), 1.61 (m, 3H), 1.47 (m, 2H), 1.38 (m, 1H), 1.20 (s, 3H), 1.12 (d, 3H ), 1.06 (s, 3H). Example No.1.1-125:
1H-NMR (600 MHz, CDCh δ, ppm) 7.88 (d, 1 H), 7.56 (d, 1 H), 7.44 (dd, 1 H), 7.36 (dd, 1 H), 4.38 (q, 2H), 1.98 (m, 1 H), 1.74 (m, 1 H), 1.63 (m, 1 H), 1.54 (m, 1 H), 1.48 (m, 1 H-NMR (600 MHz, CDCh δ, ppm) 7.88 (d, 1H), 7.56 (d, 1H), 7.44 (dd, 1H), 7.36 (dd, 1H), 4.38 (q, 2H ), 1.98 (m, 1H), 1.74 (m, 1H), 1.63 (m, 1H), 1.54 (m, 1H), 1.48 (m,
2H), 1.39 (t, 3H), 1.38 (m, 1H), 1.21 (s, 3H), 1.12 (d, 3H), 1.07 (s, 3H). 2H), 1.39 (t, 3H), 1.38 (m, 1H), 1.21 (s, 3H), 1.12 (d, 3H), 1.07 (s, 3H).
Beispiel No.1.1-128: Example No.1.1-128:
Ή-NMR (400 MHz, CDCh δ, ppm) 7.85 (d, 1 H), 7.55 (d, 1 H), 7.43 (m, 1 H), 7.33 (m, 1 H), 5.25 (sept, 1 H), 2.23 (br. s, 1 H, OH), 1.97 (m, 1 H), 1.76 (m, 1 H), 1.62 (m, 1 H), 1.53-1.47 (m, 3H), 1.38 (d, 6H), 1.37 (m, 1 H), 1.21 (s, 3H), 1.12 (d, 3H), 1.06 (s, 3H). Ή-NMR (400 MHz, CDCh δ, ppm) 7.85 (d, 1H), 7.55 (d, 1H), 7.43 (m, 1H), 7.33 (m, 1H), 5.25 (sept, 1H ), 2.23 (brs s, 1H, OH), 1.97 (m, 1H), 1.76 (m, 1H), 1.62 (m, 1H), 1.53-1.47 (m, 3H), 1.38 (i.e. , 6H), 1.37 (m, 1H), 1.21 (s, 3H), 1.12 (d, 3H), 1.06 (s, 3H).
Beispiel No.1.1-129: Example No.1.1-129:
1H-NMR (400 MHz, CDCh δ, ppm) 7.89 (d, 1 H), 7.57 (d, 1 H), 7.43 (m, 1 H), 7.33 (m, 1 H), 4.28 (t, 1 H), 2.23 (br. s, 1 H, OH), 1.96 (m, 1 H), 1.79 (sext, 2H), 1.77 (m, 1 H), 1 H-NMR (400 MHz, CDCh δ, ppm) 7.89 (d, 1H), 7.57 (d, 1H), 7.43 (m, 1H), 7.33 (m, 1H), 4.28 (t, 1 H), 2.23 (br s, 1 H, OH), 1.96 (m, 1 H), 1.79 (sec, 2H), 1.77 (m, 1H),
1.62 (m, 2H), 1.49 (m, 2H), 1.39 (m, 1 H), 1.21 (s, 3H), 1.12 (d, 3H), 1.06 (s, 3H), 1.01 (t, 3H). 1.62 (m, 2H), 1.49 (m, 2H), 1.39 (m, 1H), 1.21 (s, 3H), 1.12 (d, 3H), 1.06 (s, 3H), 1.01 (t, 3H).
Beispiel No.1.1-130: Example No.1.1-130:
1H-NMR (400 MHz, CDCh δ, ppm) 7.87 (d, 1 H), 7.56 (d, 1 H), 7.42 (m, 1 H), 7.32 (m, 1 H), 4.33 (t, 1 H), 2.22 (br. s, 1 H, OH), 1.98 (m, 1 H), 1.78-1.71 (m, 3H), 1.61 (m, 2H), 1.52-1.44 (m, 4H), 1.38 (m, 1H), 1.21 (s, 3H), 1.13 (d, 3H), 1.06 (s, 3H), 0.99 (t, 3H). 1 H-NMR (400 MHz, CDCh δ, ppm) 7.87 (d, 1H), 7.56 (d, 1H), 7.42 (m, 1H), 7.32 (m, 1H), 4.33 (t, 1 H), 2.22 (br s, 1H, OH), 1.98 (m, 1H), 1.78-1.71 (m, 3H), 1.61 (m, 2H), 1.52-1.44 (m, 4H), 1.38 ( m, 1H), 1.21 (s, 3H), 1.13 (d, 3H), 1.06 (s, 3H), 0.99 (t, 3H).
Beispiel No.1.1-131:Example No.1.1-131:
H-NMR (400 MHz, CDCh δ, ppm) 7.89 (d, 1 H), 7.53 (m, 1 H), 7.42 (m, 1 H), 7.35 (m, 1 H), 4.31 (t, 1 H), 2.20 (br. s, 1 H, OH), 1.96 (m, 1 H), 1.77-1.71 (m, 3H), 1.63-1.55 (m, 2H), 1.52-1.47 (m, 3H), 1.42-1.33 (m, 5H), 1.21 (s, 3H), 1.12 (d, 3H), 1.06 (s, 3H), 0.92 (t, 3H). H-NMR (400 MHz, CDCh δ, ppm) 7.89 (d, 1H), 7.53 (m, 1H), 7.42 (m, 1H), 7.35 (m, 1H), 4.31 (t, 1H ), 2.20 (brs s, 1H, OH), 1.96 (m, 1H), 1.77-1.71 (m, 3H), 1.63-1.55 (m, 2H), 1.52-1.47 (m, 3H), 1.42 -1.33 (m, 5H), 1.21 (s, 3H), 1.12 (d, 3H), 1.06 (s, 3H), 0.92 (t, 3H).
Beispiel No.1.1-132: Example No.1.1-132:
1H-NMR (400 MHz, CDCh δ, ppm) 7.93 (d, 1 H), 7.55 (d, 1 H), 7.45 (m, 1 H), 7.35 (m, 1 H), 4.50 (m, 2H), 3.75 (m, 2H), 3.43 (s, 3H), 3.25 (br. s, 1 H, OH), 1.97 (m, 1 H), 1.72 1 H-NMR (400 MHz, CDCh δ, ppm) 7.93 (d, 1H), 7.55 (d, 1H), 7.45 (m, 1H), 7.35 (m, 1H), 4.50 (m, 2H ), 3.75 (m, 2H), 3.43 (s, 3H), 3.25 (br s, 1 H, OH), 1.97 (m, 1 H), 1.72
(m, 1H), 1.62 (m, 1H), 1.56 (m, 1H), 1.48 (m,2H), 1.39 (m, 1H), 1.17 (s,3H), 1.10 (d, 3H), 1.06 (s, 3H).
Beispiel No.1.1-133: (m, 1H), 1.62 (m, 1H), 1.56 (m, 1H), 1.48 (m, 2H), 1.39 (m, 1H), 1.17 (s, 3H), 1.10 (d, 3H), 1.06 ( s, 3H). Example No.1.1-133:
1H-NMR (400 MHz, CDCh δ, ppm) 7.90 (d, 1 H), 7.54 (m, 1 H), 7.47 (m, 1 H), 7.35 (m, 1H), 4.42 (t, 1H).3.56 (t, 2H), 3.35 (s, 3H), 2.55 (br. s, 1H, OH), 2.04 (quint, 2H), 1.96 1 H-NMR (400 MHz, CDCh δ, ppm) 7.90 (d, 1H), 7.54 (m, 1H), 7.47 (m, 1H), 7.35 (m, 1H), 4.42 (t, 1H) .3.56 (t, 2H), 3.35 (s, 3H), 2.55 (br s, 1H, OH), 2.04 (quint, 2H), 1.96
(m, 1 H), 1.72 (m, 1 H), 1.62 (m, 1 H), 1.52-1.44 (m, 3H), 1.38 (m, 1 H), 1.20 (s, 3H), 1.12 (d.3H).1.06 (s, 3H). (m, 1H), 1.72 (m, 1H), 1.62 (m, 1H), 1.52-1.44 (m, 3H), 1.38 (m, 1H), 1.20 (s, 3H), 1.12 (i.e. .3H) .1.06 (s, 3H).
Beispiel No.1.1-134: Example No.1.1-134:
1H-NMR (400 MHz, CDCh δ, ppm) 7.94 (d, 1 H), 7.53 (m, 1 H), 7.43 (m, 1 H), 7.34 (m, 1H), 4.48 (m, 1H), 3.79 (m, 2H), 3.60 (q, 2H), 3.02 (br. s, 1H, OH), 1.97 (m, 1H), 1.72 (m, 1 H), 1.62 (m, 1 H), 1.54-1.50 (m, 2H), 1.49-1.46 (m, 2H), 1.38 (m, 1 H), 1.24 (t, 3H), 1.18 (s, 3H), 1.11 (d, 3H), 1.06 (s, 3H). 1 H-NMR (400 MHz, CDCh δ, ppm) 7.94 (d, 1H), 7.53 (m, 1H), 7.43 (m, 1H), 7.34 (m, 1H), 4.48 (m, 1H) , 3.79 (m, 2H), 3.60 (q, 2H), 3.02 (br, s, 1H, OH), 1.97 (m, 1H), 1.72 (m, 1H), 1.62 (m, 1H), 1.54 -1.50 (m, 2H), 1.49-1.46 (m, 2H), 1.38 (m, 1H), 1.24 (t, 3H), 1.18 (s, 3H), 1.11 (d, 3H), 1.06 (s, 3H).
Beispiel No.1.1-135: Example No.1.1-135:
1H-NMR (400 MHz, CDCh δ, ppm) 7.97 (d, 1 H), 7.56 (d, 1 H), 7.47 (m, 1 H), 7.37 (m, 1 H), 4.93 (d, 2H), 2.52 (t, 1 H), 2.28 (br. s, 1 H, OH), 1.98 (m, 1 H), 1.74 (m, 1 H), 1.62 (m, 1 H), 1.52-1.42 (m, 3H), 1.40 (m, 1 H), 1.20 (s, 3H), 1.13 (d, 3H), 1.06 (s, 3H). 1 H-NMR (400 MHz, CDCh δ, ppm) 7.97 (d, 1H), 7.56 (d, 1H), 7.47 (m, 1H), 7.37 (m, 1H), 4.93 (d, 2H ), 2.52 (t, 1H), 2.28 (brs s, 1H, OH), 1.98 (m, 1H), 1.74 (m, 1H), 1.62 (m, 1H), 1.52-1.42 ( m, 3H), 1.40 (m, 1H), 1.20 (s, 3H), 1.13 (d, 3H), 1.06 (s, 3H).
Beispiel No.1.1-136:Example No.1.1-136:
H-NMR (400 MHz, CDCh 6, ppm) 7.96 (d, 1 H), 7.56 (d, 1 H), 7.48 (m, 1 H), 7.36 (m, 1 H), 4.89 (m, 2H), 2.52 (t, 1 H), 1.97 (m, 2H), 1.87 (m, 3H), 1.73 (m, 1 H), 1.61 (m, 1 H), 1.54-1.42 (m, 3H), 1.38 (m, 1H), 1.20 (s, 3H), 1.13 (d, 3H), 1.06 (s, 3H). H NMR (400 MHz, CDCh6, ppm) 7.96 (d, 1H), 7.56 (d, 1H), 7.48 (m, 1H), 7.36 (m, 1H), 4.89 (m, 2H) , 2.52 (t, 1H), 1.97 (m, 2H), 1.87 (m, 3H), 1.73 (m, 1H), 1.61 (m, 1H), 1.54-1.42 (m, 3H), 1.38 m, 1H), 1.20 (s, 3H), 1.13 (d, 3H), 1.06 (s, 3H).
Beispiel No.1.1-137:Example No.1.1-137:
H-NMR (400 MHz, CDCh δ, ppm) 7.93 (d, 1 H), 7.57 (d, 1 H), 7.47 (m, 1 H), 7.35 (m, 1 H), 6.05 (m, 1 H), 5.42 (m, 1 H), 5.29 (m, 1 H), 4.83 (m, 1 H), 1.98 (m, 2H), 1.82 (br. s, 1H, OH), 1.74 (m, 1H), 1.61 (m, 1H), 1.53-1.42 (m, 3H), 1.39 (m, 1H), 1.19 (s, 3H), 1.12 (d.3H), 1.06 (s.3H). H-NMR (400 MHz, CDCh δ, ppm) 7.93 (d, 1H), 7.57 (d, 1H), 7.47 (m, 1H), 7.35 (m, 1H), 6.05 (m, 1H ), 5.42 (m, 1H), 5.29 (m, 1H), 4.83 (m, 1H), 1.98 (m, 2H), 1.82 (br s, 1H, OH), 1.74 (m, 1H) , 1.61 (m, 1H), 1.53-1.42 (m, 3H), 1.39 (m, 1H), 1.19 (s, 3H), 1.12 (d.3H), 1.06 (s.3H).
Beispiel No.1.1-139:Example No.1.1-139:
H-NMR (400 MHz, CHCh) d 8.11 (d.1 H), 7.56 (d, 1 H), 7.47 (dd, 1 H), 7.35 (dd, 1 H), 4.26 (m, 1H), 2.27 (br. s, 1H, OH), 1.98 (m, 2H), 1.92 (m, 1H), 1.68 (m, 1H), 1.61 (m, 1H), 1.49 (m, 1H), 1.43 (m, 2H), 1.36 (m, 1H), 1.30 (d, 3H), 1.17 (s, 3H), 1.10 (d, 3H), 1.06, (s, 3H), 0.98 (t, 3H).
Beispiel No.1.1-140: H-NMR (400 MHz, CHCh) d 8.11 (d.1 H), 7.56 (d, 1 H), 7.47 (dd, 1 H), 7.35 (dd, 1 H), 4.26 (m, 1H), 2.27 (brs s, 1H, OH), 1.98 (m, 2H), 1.92 (m, 1H), 1.68 (m, 1H), 1.61 (m, 1H), 1.49 (m, 1H), 1.43 (m, 2H ), 1.36 (m, 1H), 1.30 (d, 3H), 1.17 (s, 3H), 1.10 (d, 3H), 1.06, (s, 3H), 0.98 (t, 3H). Example No.1.1-140:
1H-NMR (400 MHz, CDCh δ, ppm) 8.05 (d, 1 H), 7.58 (d, 1 H), 7.50 (dd, 1 H), 7.39 (dd, 1 H), 3.65 (m, 1 H), 2.68 (br. s, 1 H, OH), 1.97 (m, 1 H), 1.74 (m, 1 H), 1.63 (m, 2H), 1.54- 1.44 (m, 4H), 1.38 (m, 3H), 1.28 (m, 4H).1.21 (s, 3H), 1.12 (d, 3H), 1.06 (s, 3H), 0.88 (m,2H). 1 H-NMR (400 MHz, CDCh δ, ppm) 8.05 (d, 1H), 7.58 (d, 1H), 7.50 (dd, 1H), 7.39 (dd, 1H), 3.65 (m, 1 H), 2.68 (brs s, 1H, OH), 1.97 (m, 1H), 1.74 (m, 1H), 1.63 (m, 2H), 1.54- 1.44 (m, 4H), 1.38 (m , 3H), 1.28 (m, 4H) .1.21 (s, 3H), 1.12 (d, 3H), 1.06 (s, 3H), 0.88 (m, 2H).
Beispiel No.1.1-142: Example No.1.1-142:
1H-NMR (400 MHz, CDCh δ, ppm) 7.97 (d, 1 H), 7.59 (d, 1 H), 7.50 (dd, 1 H), 7.38 (dd, 1 H), 6.24-5.97 (tt, 1 H), 4.53 (dt, 2H), 2.20 (br. s, 1 H, OH), 1.98 (m, 1 H), 1.72 (m, 1 H), 1 H-NMR (400 MHz, CDCh δ, ppm) 7.97 (d, 1H), 7.59 (d, 1H), 7.50 (dd, 1H), 7.38 (dd, 1H), 6.24-5.97 (tt , 1 H), 4.53 (dt, 2H), 2.20 (br s, 1 H, OH), 1.98 (m, 1 H), 1.72 (m, 1 H),
1.62 (m, 1H), 1.52 (m, 1H), 1.48 (m, 2H), 1.38 (m, 1H), 1.20 (s, 3H), 1.12 (d,3H), 1.06 (s, 3H). 1.62 (m, 1H), 1.52 (m, 1H), 1.48 (m, 2H), 1.38 (m, 1H), 1.20 (s, 3H), 1.12 (d, 3H), 1.06 (s, 3H).
Beispiel No.1.1-155: Example No.1.1-155:
1H-NMR (400 MHz, CDCh δ, ppm) 7.95 (m, 1 H), 7.50 (m, 1 H), 7.39 (m, 2H), 6.98 (br. s, 1H, NH), 4.30 (m, 1H), 2.00 (m, 1H), 1.95 (s, 1H, OH), 1.70 (m, 2H), 1.50 (m, 2H), 1.40 (m, 2H), 1.30 (d, 6H), 1.20 (s, 3H), 1.11 (d, 3H), 1.08 (s, 3H). 1H-NMR (400 MHz, CDCh δ, ppm) 7.95 (m, 1H), 7.50 (m, 1H), 7.39 (m, 2H), 6.98 (br.s, 1H, NH), 4.30 (m, 1H), 2.00 (m, 1H), 1.95 (s, 1H, OH), 1.70 (m, 2H), 1.50 (m, 2H), 1.40 (m, 2H), 1.30 (d, 6H), 1.20 (s , 3H), 1.11 (d, 3H), 1.08 (s, 3H).
Beispiel No.1.1-156:Example No.1.1-156:
H-NMR (400 MHz, CDCh δ, ppm) 8.01 (m, 1 H), 7.50 (m, 1 H), 7.40 (m, 2H), 2.91 (m, 1 H), 2.00 (m, 1 H), 1.95 (s, 1 H, OH), 1.68 (m, 2H), 1.56 (s, 4H), 1.50-1.38 (m, 2H), 1.20 (s, 3H), 1.11 (d, 3H), 1.08 (s, 3H), 0.85 (m, 2H), 0.68 (m, 2H). H NMR (400 MHz, CDCh δ, ppm) 8.01 (m, 1H), 7.50 (m, 1H), 7.40 (m, 2H), 2.91 (m, 1H), 2.00 (m, 1H) , 1.95 (s, 1H, OH), 1.68 (m, 2H), 1.56 (s, 4H), 1.50-1.38 (m, 2H), 1.20 (s, 3H), 1.11 (d, 3H), 1.08 ( s, 3H), 0.85 (m, 2H), 0.68 (m, 2H).
Beispiel No.1.1-157:Example No.1.1-157:
H-NMR (400 MHz, CDCh δ, ppm) 7.98 (m, 1 H), 7.50 (m, 1 H), 7.40 (m, 2H), 7.31 (br. s, 1H, NH), 4.60 (m, 1H), 2.41 (m, 2H), 2.06 (m, 3H), 1.97 (s, 1H, OH), 1.80-1.62 (m, 4H), 1.52-1.40 (m, 4H), 1.20 (s.3H), 1.11 (d, 3H), 1.08 (s, 3H). H NMR (400 MHz, CDCh δ, ppm) 7.98 (m, 1H), 7.50 (m, 1H), 7.40 (m, 2H), 7.31 (br, s, 1H, NH), 4.60 (m, 1H), 2.41 (m, 2H), 2.06 (m, 3H), 1.97 (s, 1H, OH), 1.80-1.62 (m, 4H), 1.52-1.40 (m, 4H), 1.20 (s.3H) , 1.11 (d, 3H), 1.08 (s, 3H).
Beispiel No.1.1-160:Example No.1.1-160:
H-NMR (400 MHz, CDCh δ, ppm) 8.00 (m, 1 H), 7.50 (m, 1 H), 7.40 (m, 2H), 7.22 (br. s, 1H, NH), 3.43 (q, 2H), 1.98 (m, 2H), 1.65 (m, 4H), 1.50-1.38 (m, 4H), 1.20 (s, 3H), 1.11 (d, 3H), 1.08 (s, 3H), 0.98 (t, 3H).
Beispiel No.1.1-161: H NMR (400 MHz, CDCh δ, ppm) 8.00 (m, 1H), 7.50 (m, 1H), 7.40 (m, 2H), 7.22 (br, s, 1H, NH), 3.43 (q, 2H), 1.98 (m, 2H), 1.65 (m, 4H), 1.50-1.38 (m, 4H), 1.20 (s, 3H), 1.11 (d, 3H), 1.08 (s, 3H), 0.98 (t , 3H). Example No.1.1-161:
1H-NMR (400 MHz, CDCh δ, ppm) 7.98 (m, 1H), 7.51 (m, 1H), 7.40 (m, 2H), 7.21 (br. s, 1H, NH), 3.30 (t, 2H), 2.02 (s, 1H, OH), 1.98-1.89 (m, 2H), 1.67-1.35 (m, 6H), 1.18 1 H-NMR (400 MHz, CDCh δ, ppm) 7.98 (m, 1H), 7.51 (m, 1H), 7.40 (m, 2H), 7.21 (br.s, 1H, NH), 3.30 (t, 2H ), 2.02 (s, 1H, OH), 1.98-1.89 (m, 2H), 1.67-1.35 (m, 6H), 1.18
(s, 3H), 1.11 (d, 3H), 1.08 (s, 3H), 0.98 (d, 6H). (s, 3H), 1.11 (d, 3H), 1.08 (s, 3H), 0.98 (d, 6H).
Beispiel No.1.1-162: Example No.1.1-162:
1H-NMR (400 MHz, CDCh δ, ppm) 8.02 (m, 1 H), 7.57 (br. s, 1 H, NH), 7.52 (m, 1 H), 7.43 (m, 2H), 4.29 (m, 2H), 2.29 (m, 1H), 2.19 (s, 1H, OH), 1.98 (m, 1H), 1.70-1.62 (m, 2H).1.58-1.49 (m, 2H), 1.47-1.36 (m, 2H).1.20 (s, 3H), 1.13 (d, 3H), 1.07 (s, 3H). 1 H-NMR (400 MHz, CDCh δ, ppm) 8.02 (m, 1H), 7.57 (br.s, 1H, NH), 7.52 (m, 1H), 7.43 (m, 2H), 4.29 ( m, 2H), 2.29 (m, 1H), 2.19 (s, 1H, OH), 1.98 (m, 1H), 1.70-1.62 (m, 2H) .1.58-1.49 (m, 2H), 1.47-1.36 ( m, 2H) .1.20 (s, 3H), 1.13 (d, 3H), 1.07 (s, 3H).
Beispiel No.1.1-163:Example No.1.1-163:
H-NMR (400 MHz, CDCh δ, ppm) 8.01 (m, 1 H), 7.51 (m, 1 H), 7.42 (m, 3H), 4.22 (m, 2H), 2.29 (br. s, 1 H, OH), 2.00 (m, 1 H), 1.83 (t, 3H), 1.70-1.62 (m, 2H), 1.58-1.49 (m, 2H), 1.42 (m, 2H), 1.20 (s, 3H), 1.13 (d, 3H), 1.07 (s, 3H). H-NMR (400 MHz, CDCh δ, ppm) 8.01 (m, 1H), 7.51 (m, 1H), 7.42 (m, 3H), 4.22 (m, 2H), 2.29 (br. S, 1H , OH), 2.00 (m, 1H), 1.83 (t, 3H), 1.70-1.62 (m, 2H), 1.58-1.49 (m, 2H), 1.42 (m, 2H), 1.20 (s, 3H) , 1.13 (d, 3H), 1.07 (s, 3H).
Beispiel No.1.1-164:Example No.1.1-164:
H-NMR (400 MHz, CDCh δ, ppm) 8.11 (m, 2H), 7.54 (m, 1 H), 7.48 (m, 2H), 4.38 (d, 2H), 2.12 (s, 1H, OH), 2.00 (m, 1H), 1.71-1.35 (m, 6H), 1.20 (s, 3H), 1.11 (d, 3H), 1.09 (s, 3H). H-NMR (400 MHz, CDCh δ, ppm) 8.11 (m, 2H), 7.54 (m, 1H), 7.48 (m, 2H), 4.38 (d, 2H), 2.12 (s, 1H, OH), 2.00 (m, 1H), 1.71-1.35 (m, 6H), 1.20 (s, 3H), 1.11 (d, 3H), 1.09 (s, 3H).
Beispiel No.1.1-165:Example No.1.1-165:
H-NMR (400 MHz, CDCh δ, ppm) 7.49 (m, 1 H), 7.32 (m, 2H), 7.25 (m, 1 H), 3.10 (s, 3H), 2.88 (s, 3H), 1.97 (s, 1H, OH), 1.92 (m, 1H), 1.60-1.35 (m, 6H), 1.16 (s, 3H), 1.08 (d, 3H), 1.03 (s, 3H). H-NMR (400 MHz, CDCh δ, ppm) 7.49 (m, 1H), 7.32 (m, 2H), 7.25 (m, 1H), 3.10 (s, 3H), 2.88 (s, 3H), 1.97 (s, 1H, OH), 1.92 (m, 1H), 1.60-1.35 (m, 6H), 1.16 (s, 3H), 1.08 (d, 3H), 1.03 (s, 3H).
Beispiel No.1.1-167:Example No.1.1-167:
H-NMR (400 MHz, CDCh δ, ppm) 7.49 (m, 1H), 7.32 (m, 2H), 7.22 (m, 1H), 4.15 (br. d, 1H), 3.28 (br. d, 2H), 3.14 (br. d, 1H), 2.00 (s, 1H, OH), 1.91 (m, 1H), 1.70-1.35 (m, H-NMR (400 MHz, CDCh δ, ppm) 7.49 (m, 1H), 7.32 (m, 2H), 7.22 (m, 1H), 4.15 (br, d, 1H), 3.28 (br, d, 2H) , 3.14 (brd, 1H), 2.00 (s, 1H, OH), 1.91 (m, 1H), 1.70-1.35 (m,
12H), 1.18 (s, 3H), 1.09 (d, 3H), 1.03 (s, 3H).
Beispiel No.1.1-168:12H), 1.18 (s, 3H), 1.09 (d, 3H), 1.03 (s, 3H). Example No.1.1-168:
H-NMR (400 MHz, CDCh δ, ppm) 8.11 (m, 1 H), 7.91 (br. s, 1 H, NH), 7.50 (m, 1 H), 7.41 (m, 2H), 3.70 (m, 5H), 3.41 (s, 3H), 1.99 (m, 1H), 1.68-1.40 (m, 6H), 1.15 (s, 3H), 1.09 (d, 6H). H-NMR (400 MHz, CDCh δ, ppm) 8.11 (m, 1H), 7.91 (br, s, 1H, NH), 7.50 (m, 1H), 7.41 (m, 2H), 3.70 (m , 5H), 3.41 (s, 3H), 1.99 (m, 1H), 1.68-1.40 (m, 6H), 1.15 (s, 3H), 1.09 (d, 6H).
Beispiel No.1.1-169: Example No.1.1-169:
1H-NMR (400 MHz, CDCh δ, ppm) 8.12 (m, 2H), 7.52 (m, 1H), 7.43 (m, 2H), 4.31 (d, 2H), 3.81 (s, 3H), 3.65 (br. s, 1H, OH), 2.00 (m, 1H), 1.68-1.40 (m, 6H), 1.18 (s, 3H), 1.09 (m, 6H). 1 H-NMR (400 MHz, CDCh δ, ppm) 8.12 (m, 2H), 7.52 (m, 1H), 7.43 (m, 2H), 4.31 (d, 2H), 3.81 (s, 3H), 3.65 ( br. s, 1H, OH), 2.00 (m, 1H), 1.68-1.40 (m, 6H), 1.18 (s, 3H), 1.09 (m, 6H).
Beispiel No.1.1-170:Example No.1.1-170:
H-NMR (400 MHz, CDCh δ, ppm) 7.49 (m, 1H), 7.35 (m, 3H), 4.30 (br. s, 2H), 3.80/3.70 (s, 3H), 3.12/2.98 (s, 3H), 1.94 (m, 1H), 1.60-1.35 (m, 7H), 1.14 (m, 3H), 1.06 (m, 6H) H-NMR (400 MHz, CDCh δ, ppm) 7.49 (m, 1H), 7.35 (m, 3H), 4.30 (br, s, 2H), 3.80 / 3.70 (s, 3H), 3.12 / 2.98 (s, 3H), 1.94 (m, 1H), 1.60-1.35 (m, 7H), 1.14 (m, 3H), 1.06 (m, 6H)
Beispiel No.1.1-172:Example No.1.1-172:
H-NMR (400 MHz, CDCh 6, ppm) 8.31 (br. s, 1H, NH), 8.17 (m, 1H), 7.51 (m, 1H), 7.41 (m, 2H), 3.88 (s, 1H, OH), 3.75 (m, 2H), 3.71 (s, 3H), 2.70 (t, 2H), 2.00 (m, 1H), 1.68 (m, 2H), 1.60-1.40 (m, 4H), 1.21 (s, 3H), 1.11 (d, 3H), 1.10 (s, 3H). H-NMR (400 MHz, CDCh 6, ppm) 8.31 (br.s, 1H, NH), 8.17 (m, 1H), 7.51 (m, 1H), 7.41 (m, 2H), 3.88 (s, 1H, OH), 3.75 (m, 2H), 3.71 (s, 3H), 2.70 (t, 2H), 2.00 (m, 1H), 1.68 (m, 2H), 1.60-1.40 (m, 4H), 1.21 (s , 3H), 1.11 (d, 3H), 1.10 (s, 3H).
Beispiel No.1.1-173: Example No.1.1-173:
1H-NMR (400 MHz, CDCh 6, ppm) 8.15 (br. s, 1H, NH), 8.12 (m, 1H), 7.51 (m, 1H), 7.40 (m, 2H), 4.64 (m, 1H), 4.18 (q, 2H), 3.99 (br. d, 1H, OH), 2.74 (m, 1H), 2.68 (m, 1 H), 2.01 (m, 1 H), 1.69 (m, 1 H), 1.62 (m, 1 H), 1.54 (m, 1 H), 1.43 (m, 1 H), 1.39 (m, 3H), 1.24 (t, 3H), 1.20 (s, 3H), 1.13 (d, 3H), 1.09 (s, 3H). 1 H-NMR (400 MHz, CDCh 6, ppm) 8.15 (br.s, 1H, NH), 8.12 (m, 1H), 7.51 (m, 1H), 7.40 (m, 2H), 4.64 (m, 1H ), 4.18 (q, 2H), 3.99 (br d, 1H, OH), 2.74 (m, 1H), 2.68 (m, 1H), 2.01 (m, 1H), 1.69 (m, 1H) , 1.62 (m, 1H), 1.54 (m, 1H), 1.43 (m, 1H), 1.39 (m, 3H), 1.24 (t, 3H), 1.20 (s, 3H), 1.13 (d, 3H), 1.09 (s, 3H).
Beispiel No.1.1-177:Example No.1.1-177:
H-NMR (400 MHz, CDCh δ, ppm) 7.46 (m, 1H), 7.34 (m, 3H), 4.63 (m, 1H), 3.80 (s, 3H), 3.70 (br. s, 1H, OH), 3.28 (m, 1H), 2.28 (m, 1H), 2.05-1.88 (m, 4H), 1.65-1.35 (m, 6H), 1.15 (m, 3H), 1.06 (m, 6H).
Beispiel No.1.1-181:H-NMR (400 MHz, CDCh δ, ppm) 7.46 (m, 1H), 7.34 (m, 3H), 4.63 (m, 1H), 3.80 (s, 3H), 3.70 (br. S, 1H, OH) , 3.28 (m, 1H), 2.28 (m, 1H), 2.05-1.88 (m, 4H), 1.65-1.35 (m, 6H), 1.15 (m, 3H), 1.06 (m, 6H). Example No.1.1-181:
H-NMR (400 MHz, CDCh δ, ppm) 8.29 (br. d, 1H, NH), 8.13 (m, 1H), 7.53 (m, 1H), H-NMR (400 MHz, CDCh δ, ppm) 8.29 (br.d, 1H, NH), 8.13 (m, 1H), 7.53 (m, 1H),
7.42 (m, 2H), 4.91 (m.1H), 3.86 (br. s, 1H, OH), 3.85 (s, 3H), 2.02 (m, 1H), 1.69 (m, 2H), 1.55 (d, 3H), 1.54 (m, 2H), 1.42 (m, 2H), 1.18 (d, 3H), 1.09 (s, 3H), 1.08 (s, 3H). 7.42 (m, 2H), 4.91 (m.1H), 3.86 (br s, 1H, OH), 3.85 (s, 3H), 2.02 (m, 1H), 1.69 (m, 2H), 1.55 (d, 3H), 1.54 (m, 2H), 1.42 (m, 2H), 1.18 (d, 3H), 1.09 (s, 3H), 1.08 (s, 3H).
Beispiel No.1.1-183:Example No.1.1-183:
H-NMR (400 MHz, CDCh δ, ppm) 8.17 (m, 1H), 8.12 (br. d, 1H, NH), 7.52 (m, 1H), H NMR (400 MHz, CDCh δ, ppm) 8.17 (m, 1H), 8.12 (br d, 1H, NH), 7.52 (m, 1H),
7.41 (m, 2H), 4.30 (m, 1 H), 4.25 / 4.22 (br. s, 1 H, OH), 3.69 (s, 3H), 2.77 (m, 1 H), 2.727.41 (m, 2H), 4.30 (m, 1H), 4.25 / 4.22 (br s, 1H, OH), 3.69 (s, 3H), 2.77 (m, 1H), 2.72
(m, 1H), 2.10 (m, 1H), 2.01 (m, 1H), 1.69 (m, 2H), 1.53 (m, 2H), 1.47-1.40 (m, 2H), 1.19 (s, 3H), 1.11 (d, 3H), 1.09 (s, 3H), 1.00 (m, 3H), 0.96 (m, 3H). (m, 1H), 2.10 (m, 1H), 2.01 (m, 1H), 1.69 (m, 2H), 1.53 (m, 2H), 1.47-1.40 (m, 2H), 1.19 (s, 3H), 1.11 (d, 3H), 1.09 (s, 3H), 1.00 (m, 3H), 0.96 (m, 3H).
Beispiel No.1.1-184:Example No.1.1-184:
H-NMR (400 MHz, CDCh δ, ppm) 8.28 (br. m, 1H, NH), 8.16 (m, 1H), 7.54 (m, 1H), H NMR (400 MHz, CDCh δ, ppm) 8.28 (br, m, 1H, NH), 8.16 (m, 1H), 7.54 (m, 1H),
7.43 (m, 2H), 4.89 (m, 1H), 4.29 (q, 2H), 4.21 (br. m, 1H, OH), 2.28 (m, 1H), 2.02 (m, 1 H), 1.69 (m, 2H), 1.54 (m, 2H), 1.44 (m, 2H), 1.31 (t, 3H), 1.20 (s, 3H), 1.11 (d, 3H),7.43 (m, 2H), 4.89 (m, 1H), 4.29 (q, 2H), 4.21 (br, m, 1H, OH), 2.28 (m, 1H), 2.02 (m, 1H), 1.69 (m , 2H), 1.54 (m, 2H), 1.44 (m, 2H), 1.31 (t, 3H), 1.20 (s, 3H), 1.11 (d, 3H),
1.09 (s, 3H), 1.01 (m, 6H). 1.09 (s, 3H), 1.01 (m, 6H).
Beispiel No.1.1-185:Example No.1.1-185:
H-NMR (400 MHz, CDCh δ, ppm) 8.83 (br. m, 1H, NH), 8.19 (m, 1H), 7.53 (m, 1H), 7.43 (m, 2H), 4.89 (m, 2H), 4.66 (m, 2H), 4.26 (br. s, 1 H, OH), 4.12 (q, 2H), 3.38 (s, 2H), 2.02 (m, 1H), 1.70 (m, 2H), 1.55 (m, 2H), 1.44 (m, 2H), 1.24 (t, 3H), 1.20 (s, 3H), 1.11 (d, 3H), 1.09 (s, 3H). H-NMR (400 MHz, CDCh δ, ppm) 8.83 (br, m, 1H, NH), 8.19 (m, 1H), 7.53 (m, 1H), 7.43 (m, 2H), 4.89 (m, 2H) , 4.66 (m, 2H), 4.26 (brs s, 1H, OH), 4.12 (q, 2H), 3.38 (s, 2H), 2.02 (m, 1H), 1.70 (m, 2H), 1.55 ( m, 2H), 1.44 (m, 2H), 1.24 (t, 3H), 1.20 (s, 3H), 1.11 (d, 3H), 1.09 (s, 3H).
Beispiel No.1.1-188:Example No.1.1-188:
H-NMR (400 MHz, CDCh δ, ppm) 8.18 (br. m, 1H, NH), 8.13 (m, 1H), 7.53 (m, 1H), H-NMR (400 MHz, CDCh δ, ppm) 8.18 (br, m, 1H, NH), 8.13 (m, 1H), 7.53 (m, 1H),
7.42 (m, 2H), 4.97 (m, 1H), 4.25 (q, 2H), 4.07 (br. s, 1H, OH), 2.02 (m, 1H), 1.74-1.647.42 (m, 2H), 4.97 (m, 1H), 4.25 (q, 2H), 4.07 (br, s, 1H, OH), 2.02 (m, 1H), 1.74-1.64
(m, 4H), 1.52 (m, 1H), 1.41 (m, 2H), 1.30 (t.3H), 1.19/ 1.17 (s, 3H), 1.10 (d,3H), 1.08 (s, 3H), 0.98 (m, 6H). Beispiel No.1.1-190:(m, 4H), 1.52 (m, 1H), 1.41 (m, 2H), 1.30 (t.3H), 1.19 / 1.17 (s, 3H), 1.10 (d, 3H), 1.08 (s, 3H), 0.98 (m, 6H). Example No.1.1-190:
H-NMR (400 MHz, CDCh δ, ppm) 8.08 (m, 1 H), 7.67 (br. t, 1 H, NH), 7.50 (m, 1 H), H-NMR (400 MHz, CDCh δ, ppm) 8.08 (m, 1H), 7.67 (br.t, 1H, NH), 7.50 (m, 1H),
7.43 (m, 2H), 3.91 (s, 3H), 3.55 (m, 2H), 3.05 (br. s, 1 H, OH), 2.41 (t, 2H), 2.00 (m,
3H), 1.68 (m, 2H), 1.59 (m, 1H), 1.50 (m, 1H), 1.42 (m, 2H), 1.21 (s, 3H), 1.12 (d, 3H), 1.08 (s, 3H). 7.43 (m, 2H), 3.91 (s, 3H), 3.55 (m, 2H), 3.05 (br, s, 1H, OH), 2.41 (t, 2H), 2.00 (m, 3H), 1.68 (m, 2H), 1.59 (m, 1H), 1.50 (m, 1H), 1.42 (m, 2H), 1.21 (s, 3H), 1.12 (d, 3H), 1.08 (s, 3H ).
Beispiel No.1.1-191: Example No.1.1-191:
1H-NMR (400 MHz, CDCb δ, ppm) 8.02 (m, 1 H), 7.97 (br. t, 1 H, NH), 7.51 (m, 1 H), 7.42 (m, 2H), 3.71 (s, 3H), 2.71 (br. s, 1H, OH), 1.99 (m, 3H), 1.68 (m, 4H), 1.56 (m, 2H), 1.51 (m, 1H), 1.42 (m, 1H), 1.33 (m, 2H), 1.18 (s, 3H), 1.11 (d, 3H), 1.06 (s, 3H). 1H-NMR (400 MHz, CDCb δ, ppm) 8.02 (m, 1H), 7.97 (br.t, 1H, NH), 7.51 (m, 1H), 7.42 (m, 2H), 3.71 (s , 3H), 2.71 (brs s, 1H, OH), 1.99 (m, 3H), 1.68 (m, 4H), 1.56 (m, 2H), 1.51 (m, 1H), 1.42 (m, 1H), 1.33 (m, 2H), 1.18 (s, 3H), 1.11 (d, 3H), 1.06 (s, 3H).
Beispiel No.1.1-218: Example No.1.1-218:
1 H-NMR (400 MHz, CDCb δ, ppm) 8.09 (m, 1 H), 7.68 (br. t, 1 H, NH), 7.51 (m, 1 H), 7.41 (m, 2H), 4.08 (q, 2H), 3.57 (m, 2H), 3.03 (br. s, 1H, OH), 2.42 (t, 2H), 2.01 (m, 3H), 1.68 (m, 2H), 1.59 (m, 1H), 1.50 (m, 1H), 1.42 (m, 2H), 1.20 (s, 3H), 1.18 (t, 3H),1 H-NMR (400 MHz, CDCb δ, ppm) 8.09 (m, 1H), 7.68 (br.t, 1H, NH), 7.51 (m, 1H), 7.41 (m, 2H), 4.08 ( q, 2H), 3.57 (m, 2H), 3.03 (br s, 1H, OH), 2.42 (t, 2H), 2.01 (m, 3H), 1.68 (m, 2H), 1.59 (m, 1H) , 1.50 (m, 1H), 1.42 (m, 2H), 1.20 (s, 3H), 1.18 (t, 3H),
1.12 (d, 3H), 1.08 (s, 3H). Beispiel No. I.3-2: 1.12 (d, 3H), 1.08 (s, 3H). Example No. I.3-2:
1H-NMR (400 MHz, CDCb 6, ppm) 7.42 (d, 1H), 7.11 (d, 1H), 3.89 (s, 3H), 2.18 (s, 1H), 1.97 (m, 1H), 1.75 (m, 1H), 1.61 (m, 1H), 1.48 (m, 3H), 1.38 (m, 1H), 1.21 (s, 3H), 1.12 (d, 3H), 1.08 (s, 3H). Beispiel No. I.4-2: 1 H-NMR (400 MHz, CDCb 6, ppm) 7.42 (d, 1H), 7.11 (d, 1H), 3.89 (s, 3H), 2.18 (s, 1H), 1.97 (m, 1H), 1.75 ( m, 1H), 1.61 (m, 1H), 1.48 (m, 3H), 1.38 (m, 1H), 1.21 (s, 3H), 1.12 (d, 3H), 1.08 (s, 3H). Example No. I.4-2:
H-NMR (400 MHz, CDCb δ, ppm) 4.23 (q, 2H), 2.35 (m, 4H), 2.03 (br. s, 1H, OH), 1.90 (m, 1H), 1.64 (m, 4H), 1.57 (m, 2H), 1.45 (m, 2H), 1.33 (m, 2H), 1.30 (t, 3H), 1.13 (s, 3H), 1.05 (d, 3H), 1.02 (s, 3H). Beispiel No. I.4-7: H NMR (400 MHz, CDCb δ, ppm) 4.23 (q, 2H), 2.35 (m, 4H), 2.03 (br, s, 1H, OH), 1.90 (m, 1H), 1.64 (m, 4H) , 1.57 (m, 2H), 1.45 (m, 2H), 1.33 (m, 2H), 1.30 (t, 3H), 1.13 (s, 3H), 1.05 (d, 3H), 1.02 (s, 3H). Example No. I.4-7:
H-NMR (400 MHz, CDCb δ, ppm) 3.74 (s, 3H), 2.39 (m, 2H), 2.18 (m, 2H), 2.02 (s, 1H), 1.90 (m, 1H), 1.63-1.32 (m, 8H), 1.12 (s, 3H), 1.07 (m, 6H), 0.98 (m, 6H). H-NMR (400 MHz, CDCb δ, ppm) 3.74 (s, 3H), 2.39 (m, 2H), 2.18 (m, 2H), 2.02 (s, 1H), 1.90 (m, 1H), 1.63-1.32 (m, 8H), 1.12 (s, 3H), 1.07 (m, 6H), 0.98 (m, 6H).
Beispiel No. I.5-2:Example No. I.5-2:
H-NMR (400 MHz, CDCb δ, ppm) 4.23 (q, 2H), 2.70 (m, 4H), 2.02 (s, 1 H), 1.91 (m, 3H), 1.63 (m, 2H), 1.45 (m, 2H), 1.35 (m, 1H), 1.30 (t, 3H), 1.13 (s, 3H), 1.08 (d, 3H), 1.03 (s, 3H).
Beispiel No.1.6-1: H-NMR (400 MHz, CDCbδ, ppm) 4.23 (q, 2H), 2.70 (m, 4H), 2.02 (s, 1H), 1.91 (m, 3H), 1.63 (m, 2H), 1.45 ( m, 2H), 1.35 (m, 1H), 1.30 (t, 3H), 1.13 (s, 3H), 1.08 (d, 3H), 1.03 (s, 3H). Example No.1.6-1:
1H-NMR (400 MHz, CDCb δ, ppm) 3.75 (s, 3H), 2.54 (m, 4H), 2.00 (s, 1 H), 1.91 (m, 1H), 1.79 (m, 2H), 1.63-1.55 (m, 5H), 1.46 (m, 2H), 1.34 (m, 3H), 1.12 (s, 3H), 1.06 (d, 3H), 1.02 (s, 3H). 1 H-NMR (400 MHz, CDCb δ, ppm) 3.75 (s, 3H), 2.54 (m, 4H), 2.00 (s, 1H), 1.91 (m, 1H), 1.79 (m, 2H), 1.63 -1.55 (m, 5H), 1.46 (m, 2H), 1.34 (m, 3H), 1.12 (s, 3H), 1.06 (d, 3H), 1.02 (s, 3H).
Beispiel No.1.10-2: Example No.1.10-2:
1H-NMR (400 MHz, CDCb δ, ppm) 4.21 (q, 2H), 2.35 (m, 3H), 1.62 (m, 4H), 1.55 (m, 6H), 1.34 (m, 2H), 1.30 (t, 3H), 1.18 (s, 6H), 1.10 (s, 6H). Beispiel No.1.11-2: 1 H-NMR (400 MHz, CDCbδ, ppm) 4.21 (q, 2H), 2.35 (m, 3H), 1.62 (m, 4H), 1.55 (m, 6H), 1.34 (m, 2H), 1.30 ( t, 3H), 1.18 (s, 6H), 1.10 (s, 6H). Example No.1.11-2:
1H-NMR (400 MHz, CDCb δ, ppm) 4.22 (q, 2H), 2.68 (m, 4H), 2.00 (br. s, 1 H, OH), 1.92 (m, 2H), 1.57 (m, 6H), 1.34 (m, 2H), 1.30 (t, 3H), 1.20 (d, 8H), 1.11 (d, 8H). 1 H NMR (400 MHz, CDCbδ, ppm) 4.22 (q, 2H), 2.68 (m, 4H), 2.00 (br, s, 1H, OH), 1.92 (m, 2H), 1.57 (m, 6H), 1.34 (m, 2H), 1.30 (t, 3H), 1.20 (d, 8H), 1.11 (d, 8H).
Beispiel No.1.13-123: Example No.1.13-123:
Diastereomer 1 - H-NMR (400 MHz, CDCb δ, ppm) 7.72 (s, 1 H), 7.41 (d, 1 H), 7.23 (m, 1H), 3.90 (s, 3H), 2.38 (s, 3H), 1.75 (m, 3H), 1.50 (m, 3H), 1.36 (m, 2H), 1.18 (d, 6H); Diastereomer 2 - H-NMR (400 MHz, CDCb δ, ppm) 7.72 (s, 1 H), 7.43 (d, 1 H), 7.24 (m, 1H), 3.90 (s, 3H), 2.38 (s, 3H), 1.63 (m, 3H), 1.50-1.30 (m, 5H), 1.14 (m, 6H). Beispiel No.1.15-9: Diastereomer 1-H-NMR (400 MHz, CDCb δ, ppm) 7.72 (s, 1H), 7.41 (d, 1H), 7.23 (m, 1H), 3.90 (s, 3H), 2.38 (s, 3H ), 1.75 (m, 3H), 1.50 (m, 3H), 1.36 (m, 2H), 1.18 (d, 6H); Diastereomer 2 - H-NMR (400 MHz, CDCb δ, ppm) 7.72 (s, 1H), 7.43 (d, 1H), 7.24 (m, 1H), 3.90 (s, 3H), 2.38 (s, 3H ), 1.63 (m, 3H), 1.50-1.30 (m, 5H), 1.14 (m, 6H). Example No.1.15-9:
1H-NMR (400 MHz, CDCb δ, ppm) 7.10 (s, 1H), 3.89 (s, 3H), 2.30 (s, 3H), 1.68 (m, 1 H-NMR (400 MHz, CDCb δ, ppm) 7.10 (s, 1H), 3.89 (s, 3H), 2.30 (s, 3H), 1.68 (m,
4H), 1.45 (m, 3H), 1.19 (d, 3H), 1.18 (d, 3H), 1.10 (m, 2H). 4H), 1.45 (m, 3H), 1.19 (d, 3H), 1.18 (d, 3H), 1.10 (m, 2H).
Beispiel No.1.16-2:Example No.1.16-2:
H-NMR (400 MHz, CDCb δ, ppm) 4.22 (q, 2H), 2.33 (m, 4H), 1.64 (m, 9H), 1.45 (m, 4H), 1.30 (m, 3H), 1.10 (t, 6H). H-NMR (400 MHz, CDCb δ, ppm) 4.22 (q, 2H), 2.33 (m, 4H), 1.64 (m, 9H), 1.45 (m, 4H), 1.30 (m, 3H), 1.10 (t , 6H).
Beispiel No.1.16-7:Example No.1.16-7:
H-NMR (400 MHz, CDCb δ, ppm) 3.73 (s, 3H), 2.35 (m, 2H), 2.15 (m, 2H), 1.68 (m, 4H), 1.58 (m, 4H), 1.45 (m, 2H), 1.10 (m, 6H), 0.92 (s, 6H).
Beispiel No. 1.17-2:H-NMR (400 MHz, CDCb δ, ppm) 3.73 (s, 3H), 2.35 (m, 2H), 2.15 (m, 2H), 1.68 (m, 4H), 1.58 (m, 4H), 1.45 (m , 2H), 1.10 (m, 6H), 0.92 (s, 6H). Example No. 1.17-2:
H-NMR (400 MHz, CDCh δ, ppm) 4.22 (q, 2H), 2.68 (m, 4H), 1 .91 (m, 2H), 1 .68 (m, 6H), 1 .48 (m, 3H), 1 .30 (t, 3H), 1 .1 1 (d, 3H), 1 .09 (d, 3H). Gegenstand der vorliegenden Erfindung ist somit die Verwendung mindestens einer Verbindung, ausgewählt aus der Gruppe, bestehend aus erfindungsgemäß H-NMR (400 MHz, CDCh δ, ppm) 4.22 (q, 2H), 2.68 (m, 4H), 1 .91 (m, 2H), 1 .68 (m, 6H), 1 .48 (m, 3H), 1 .30 (t, 3H), 1 .1 1 (d, 3H), 1 .09 (d, 3H). The present invention thus relates to the use of at least one compound selected from the group consisting of according to the invention
substituierten 1 -(Aryiethiny!)-, l-(Heteroarylethinyl)-, l-(Heterocyclylethinyl)- und 1 - (Cyloalkenylethinyl)-cyclohexanolen der allgemeinen Formel (I), sowie von beliebigen Mischungen dieser erfindungsgemäßen substituierten 1 -(Arylethinyl)-, 1 - (Heteroarylethinyl)-, 1 -(Heterocyclylethinyl)- und 1 -(Cyloalkenylethinyl)-cyclohexanole der allgemeinen Formel (I) mit weiteren agrochemischen Wirkstoffen, zur Steigerung der Widerstandsfähigkeit von Pflanzen gegenüber abiotischen Stressfaktoren, bevorzugt Trockenstress, sowie zur Stärkung des Pflanzenwachstums und/oder zur Erhöhung des Pflanzenertrags. substituted 1 - (aryiethynyl) -, 1- (heteroarylethynyl) -, 1- (heterocyclylethynyl) - and 1 - (cycloalkenylethynyl) -cyclohexanols of the general formula (I) and of any desired mixtures of these inventive substituted 1- (arylethynyl) - , 1 - (heteroarylethynyl) -, 1 - (heterocyclylethynyl) - and 1 - (cycloalkenylethynyl) cyclohexanols of the general formula (I) with other agrochemical active ingredients to increase the resistance of plants to abiotic stress factors, preferably drought stress, and to strengthen the Plant growth and / or increase the plant yield.
Weiterer Gegenstand der vorliegenden Erfindung ist eine Sprühlösung zur Behandlung von Pflanzen, enthaltend eine zur Steigerung der Widerstandsfähigkeit von Pflanzen gegenüber abiotischen Stressfaktoren wirksame Menge von mindestens einer A further subject of the present invention is a spray solution for the treatment of plants, comprising an amount of at least one effective for increasing the resistance of plants to abiotic stress factors
Verbindung, ausgewählt aus der Gruppe, bestehend aus erfindungsgemäß A compound selected from the group consisting of according to the invention
substituierten 1 -(Arylethinyl)-, 1 -(Heteroarylethinyl)-, 1 -(Heterocyclylethinyl)- und 1 - (Cyloalkenylethinyl)-cyclohexanolen, der allgemeinen Formel (I). Zu den dabei relativierbaren abiotischen Streßbedingungen können zum Beispiel Hitze, Dürre, Kälte- und Trockenstress (Stress verursacht durch Trockenheit und/oder Wassermangel), osmotischer Streß, Staunässe, erhöhter Bodensalzgehalt, erhöhtes Ausgesetztsein an Mineralien, Ozonbedingungen, Starklichtbedingungen, beschränkte Verfügbarkeit von Stickstoffnährstoffen, beschränkte Verfügbarkeit von Phosphornährstoffen zählen. substituted 1 - (arylethynyl) -, 1 - (heteroarylethynyl) -, 1 - (heterocyclylethynyl) - and 1 - (cycloalkenylethynyl) -cyclohexanols, of the general formula (I). For example, heat, drought, cold and dry stress (stress caused by drought and / or lack of water), osmotic stress, waterlogging, increased soil salt content, increased exposure to minerals, ozone conditions, high light conditions, limited availability of nitrogen nutrients, may be among the abiotic stress conditions that can be relieved. limited availability of phosphorus nutrients.
In einer Ausführungsform kann beispielsweise vorgesehen sein, dass die For example, in one embodiment, it may be provided that the
erfindungsgemäß vorgesehenen Verbindungen, d. h. die entsprechenden Compounds provided according to the invention, d. H. the corresponding
erfindungsgemäß substituierten 1 -(Arylethinyl)-, 1 -(Heteroarylethinyl)-, 1-Substituted 1- (arylethynyl) -, 1 - (heteroarylethynyl) -, 1-
(Heterocyclylethinyl)- und 1-(Cyloalkenylethinyl)-cyclohexanole der allgemeinen Formel (I), durch eine Sprühapplikation auf entsprechende zu behandelnde Pflanzen oder Pflanzenteile aufgebracht werden. Die erfindungsgemäß vorgesehene
Verwendung der Verbindungen der allgemeinen Formel (I) oder deren Salze erfolgt vorzugsweise mit einer Dosierung zwischen 0.00005 und 3 kg/ha, besonders bevorzugt zwischen 0,0001 und 2 kg/ha, insbesondere bevorzugt zwischen 0.0005 und 1 kg/ha, im Speziellen bevorzugt zwischen 0,001 und 0.25 kg/ha. Wenn im Rahmen der vorliegenden Erfindung Abscisinsäure gleichzeitig mit erfindungsgemäß substituierten 1 -(Arylethinyl)-, l-(Heteroarylethinyl)-, l-(Heterocyclylethinyl)- und 1 - (Cyloalkenylethinyl)-cyclohexanolen der allgemeinen Formel (I), beispielsweise in Rahmen einer gemeinsamen Zubereitung oder Formulierung verwendet wird, so erfolgt die Zumischung von Abscisinsäure dabei vorzugsweise in einer Dosierung zwischen 0.0001 und 3 kg/ha, besonders bevorzugt zwischen 0.001 und 2 kg/ha, insbesondere bevorzugt zwischen 0.005 und 1 kg/ha, im Speziellen bevorzugt zwischen 0.006 und 0.25 kg/ha. (Heterocyclylethinyl) - and 1- (cycloalkenylethynyl) cyclohexanols of the general formula (I), are applied by a spray application to appropriate plants or plant parts to be treated. The inventively provided Use of the compounds of general formula (I) or salts thereof is preferably carried out with a dosage between 0.00005 and 3 kg / ha, more preferably between 0.0001 and 2 kg / ha, particularly preferably between 0.0005 and 1 kg / ha, in particular preferred between 0.001 and 0.25 kg / ha. When in the context of the present invention abscisic acid simultaneously with inventively substituted 1- (arylethynyl) -, 1- (heteroarylethynyl) -, 1- (heterocyclylethynyl) - and 1- (cycloalkenylethynyl) cyclohexanols of the general formula (I), for example in the context of the admixing of abscisic acid is preferably carried out in a dosage between 0.0001 and 3 kg / ha, more preferably between 0.001 and 2 kg / ha, particularly preferably between 0.005 and 1 kg / ha, in particular preferably between 0.006 and 0.25 kg / ha.
Unter der Bezeichnung Resistenz bzw. Widerstandsfähigkeit gegenüber abiotischem Stress werden im Rahmen der vorliegenden Erfindung verschiedenartige Vorteile für Pflanzen verstanden. Solche vorteilhaften Eigenschaften äußern sich beispielsweise in den nachfolgend genannten verbesserten Pflanzencharakteristika: verbessertes Wurzelwachstum hinsichtlich Oberfläche und Tiefe, vermehrte Ausläuferbildung oder Bestockung, stärkere und produktivere Ausläufer und Bestockungstriebe, In the context of the present invention, the term resistance or resistance to abiotic stress is understood to mean various advantages for plants. Such advantageous properties are manifested, for example, in the following improved plant characteristics: improved root growth in terms of surface area and depth, increased lagging or tillering, stronger and more productive shoots and tillers,
Verbesserung des Sproßwachstums, erhöhte Standfestigkeit, vergrößerte Improvement of shoot growth, increased stability, increased
Sprossbasisdurchmesser, vergrößerte Blattfläche, höhere Erträge an Nähr- und Inhaltsstoffen, wie z.B. Kohlenhydrate, Fette, öle, Proteine, Vitamine, Mineralstoffe, ätherische öle, Farbstoffe, Fasern, bessere Faserqualität, früheres Blühen, gesteigerte Blütenanzahl, reduzierter Gehalt an toxischen Produkten wie Mycotoxine, reduzierter Gehalt an Rückständen oder unvorteilhaften Bestandteilen jeglicher Art oder bessere Verdaulichkeit, verbesserte Lagerstabilität des Erntegutes, verbesserter Toleranz gegenüber unvorteilhaften Temperaturen, verbesserter Toleranz gegenüber Dürre und Trockenheit, wie auch Sauerstoffmangel durch Wasserüberschuß, verbesserte Toleranz gegenüber erhöhten Salzgehalten in Böden und Wasser, gesteigerte Shoot base diameter, increased leaf area, higher yields of nutrients and ingredients, e.g. Carbohydrates, fats, oils, proteins, vitamins, minerals, essential oils, dyes, fibers, better fiber quality, earlier flowering, increased number of flowers, reduced content of toxic products such as mycotoxins, reduced content of residues or unfavorable ingredients of any kind or better digestibility, improved Storage stability of the crop, improved tolerance to unfavorable temperatures, improved tolerance to drought and drought, as well as lack of oxygen due to excess water, improved tolerance to increased salt levels in soils and water, increased
Toleranz gegenüber Ozonstress, verbesserte Verträglichkeit gegenüber Herbiziden und anderen Pflanzenbehandlungsmitteln, verbesserte Wasseraufnahme und Tolerance to ozone stress, improved tolerance to herbicides and other plant treatment agents, improved water absorption and
Photosyntheseleistung, vorteilhafte Pflanzeneigenschaften, wie beispielsweise Beschleunigung der Reifung, gleichmäßigere Abreife, größere Anziehungskraft für
Nützlinge, verbesserte Bestäubung oder andere Vorteile, die einem Fachmann durchaus bekannt sind. Photosynthesis, beneficial plant properties, such as acceleration of maturation, more uniform maturity, greater attraction for Beneficials, improved pollination, or other benefits well known to those skilled in the art.
Insbesondere zeigt die erfindungsgemäße Verwendung einer oder mehrerer In particular, the use according to the invention shows one or more
Verbindungen der allgemeinen Formel (I) in der Sprühapplikation auf Pflanzen und Pflanzenteilen die beschriebenen Vorteile. Kombinationen von den erfindungsgemäß substituierten 1 -(Arylethinyl)-, l-(Heteroarylethinyl)-, l-(Heterocyclylethinyl)- und 1 - (Cyloalkenylethinyl)-cyclohexanolen der allgemeinen Formel (I) unter anderem mit Insektiziden, Lockstoffen, Akariziden, Fungiziden, Nematiziden, Herbiziden, wachstumsregulierenden Stoffen, Safenern, die Pflanzenreife beeinflussenden Stoffen und Bakteriziden können bei der Bekämpfung von Pflanzenkrankheiten und/oder zur Steigerung des Pflanzenertrags im Rahmen der vorliegenden Erfindung ebenfalls Anwendung finden. Die kombinierte Verwendung von erfindungsgemäßen Compounds of general formula (I) in the spray application to plants and parts of plants the advantages described. Combinations of the inventively substituted 1- (arylethynyl) -, 1- (heteroarylethynyl) -, 1- (heterocyclylethynyl) - and 1- (cycloalkenylethynyl) -cyclohexanols of the general formula (I) inter alia with insecticides, attractants, acaricides, fungicides, Nematicides, herbicides, growth regulators, safeners, plant maturity affecting substances and bactericides may also find application in the control of plant diseases and / or to increase plant yield in the present invention. The combined use of inventive
substituierten 1 -(Arylethinyl)-, l-(Heteroarylethinyl)-, l-(Heterocyclylethinyl)- und 1 - (Cyloalkenylethinyl)-cyclohexanolen der allgemeinen Formel (I) mit gentechnisch veränderten Sorten in Bezug auf erhöhte abiotische Stresstoleranz ist darüber hinaus ebenfalls möglich. Moreover, substituted 1 - (arylethynyl) -, 1- (heteroarylethynyl) -, 1- (heterocyclylethynyl) - and 1- (cycloalkenylethynyl) -cyclohexanols of the general formula (I) with genetically modified varieties with regard to increased abiotic stress tolerance are also possible ,
Die weiter oben genannten verschiedenartigen Vorteile für Pflanzen lassen sich bekannterweise partiell zusammenfassen und mit allgemein gültigen Begriffen belegen. Soche Begriffe sind beispielsweise die nachfolgend aufgeführten The various advantages for plants mentioned above can, as is known, be partially summarized and substantiated by generally valid terms. Soche terms are, for example, those listed below
Bezeichnungen: phytotonischer Effekt, Widerstandsfähigkeit gegenüber Terms: phytotonic effect, resistance to
Stressfaktoren, weniger Pflanzenstress, Pflanzengesundheit, gesunde Pflanzen, Pflanzenfitness, („Plant Fitness"),„Plant Wellness",„Plant Concept",„Vigor Effect", „Stress Shield", Schutzschild,„Crop Health",„Crop Health Properties",„Crop Health Products",„Crop Health Management",„Crop Health Therapy",„Plant Health", Plant Health Properties", Plant Health Products",„Plant Health Management",„Plant Health Therapy", Grünungseffekt („Greening Effect" oder„Re-greening Effect"),„Freshness" oder andere Begriffe, die einem Fachmann durchaus bekannt sind. Stress Factors, Less Plant Stress, Plant Health, Healthy Plants, Plant Fitness, Plant Wellness, Plant Concept, Vigor Effect, Stress Shield, Shield, Crop Health, Crop Health Properties "Crop Health Products", "Crop Health Management", "Crop Health Therapy", "Plant Health", Plant Health Properties, "Plant Health Products", "Plant Health Management", "Plant Health Therapy", Greening Effect (" Greening effect "or" re-greening effect ")," Freshness "or other terms that are well known to a person skilled in the art.
Im Rahmen der vorliegenden Erfindung wird unter einem guten Effekt auf die In the present invention is under a good effect on the
Widerstandsfähigkeit gegenüber abiotischem Stress nicht beschränkend
mindestens ein um im Allgemeinen 3 %, insbesondere größer als 5 % besonders bevorzugt größer als 10 % verbessertes Auflaufen, Non-limiting resistance to abiotic stress at least one emergence improved by generally 3%, in particular greater than 5%, particularly preferably greater than 10%,
mindestens einen im Allgemeinen 3 %, insbesondere größer als 5 % besonders bevorzugt größer als 10 % gesteigerten Ertrag, at least one generally 3%, in particular greater than 5%, particularly preferably greater than 10% increased yield,
· mindestens eine um im Allgemeinen 3 %, insbesondere größer als 5 % besonders bevorzugt größer als 10 % verbesserte Wurzelentwicklung, At least one improved root development by generally 3%, in particular greater than 5%, particularly preferably greater than 10%,
mindestens eine um im Allgemeinen 3 %, insbesondere größer als 5 % besonders bevorzugt größer als 10 % ansteigende Sproßgröße, at least one shoot size increasing by generally 3%, in particular greater than 5%, particularly preferably greater than 10%,
mindestens eine um im Allgemeinen 3 %, insbesondere größer als 5 % besonders bevorzugt größer als 10 % vergrößerte Blattfläche, at least one leaf area increased by generally 3%, in particular greater than 5%, particularly preferably greater than 10%,
mindestens eine um im Allgemeinen 3 %, insbesondere größer als 5 % besonders bevorzugt größer als 10 % verbesserte Photosyntheseleistung und/oder mindestens eine um im Allgemeinen 3 %, insbesondere größer als 5 % besonders bevorzugt größer als 10 % verbesserte Blütenausbildung verstanden, wobei die Effekte einzeln oder aber in beliebiger Kombination von zwei oder mehreren Effekten auftreten können. at least one generally improved by 3%, in particular greater than 5%, more preferably greater than 10% improved photosynthesis and / or at least one generally improved by 3%, in particular greater than 5%, more preferably greater than 10% improved flower formation, the effects individually or in any combination of two or more effects.
Weiterer Gegenstand der vorliegenden Erfindung ist eine Sprühlösung zur Behandlung von Pflanzen, enthaltend eine zur Steigerung der Widerstandsfähigkeit von Pflanzen gegenüber abioti sehen Stressfaktoren wirksame Menge von mindestens einer Verbindung aus der Gruppe der erfindungsgemäß substituierten l -(Arylethinyl)-, 1- (Heteroarylethinyl)-, 1 -(Heterocyclylethinyl)- und 1 -(Cyloalkenylethinyl)-cyclohexanole der allgemeinen Formel (I). Die Sprühlösung kann andere übliche Bestandteile aufweisen, wie Lösungsmittel, Formulierhilfsstoffe, insbesondere Wasser, enthalten. Weitere Bestandteile können unter anderem agrochemische Wirkstoffe sein, welche unten noch weiter beschrieben werden. The present invention further provides a spray solution for the treatment of plants, comprising an amount of at least one compound from the group of the inventively substituted 1- (arylethynyl) -, 1- (heteroarylethynyl) - groups effective for increasing the resistance of plants to abiotic stress factors. , 1 - (Heterocyclylethinyl) - and 1 - (cycloalkenylethynyl) cyclohexanols of the general formula (I). The spray solution may comprise other conventional ingredients, such as solvents, formulation auxiliaries, especially water. Other ingredients may include agrochemical agents, which are further described below.
Weiterer Gegenstand der vorliegenden Erfindung ist die Verwendung von Another object of the present invention is the use of
entsprechenden Sprühlösungen zur Steigerung der Widerstandsfähigkeit von Pflanzen gegenüber abiotischen Stressfaktoren. Die nachfolgenden Ausführungen gelten sowohl für die erfindungsgemäße Verwendung einer oder mehrerer Verbindungen der allgemeinen Formel (I) an sich als auch für die entsprechenden Sprühlösungen.
Erfindunsgemäß wurde darüber hinaus gefunden, dass die Anwendung einer oder mehrerer Verbindungen der allgemeinen Formel (I) in Kombination mit mindestens einem Düngemittel wie weiter unten stehend definiert auf Pflanzen oder in deren Umgebung möglich ist. corresponding spray solutions to increase the resistance of plants to abiotic stress factors. The following statements apply both to the inventive use of one or more compounds of general formula (I) per se and for the corresponding spray solutions. According to the invention, moreover, it has been found that the use of one or more compounds of general formula (I) in combination with at least one fertilizer as defined below is possible on plants or in their environment.
Düngemittel, die erfindungsgemäß zusammen mit den oben näher erläuterten erfindungsgemäß substituierten Verbindungen der allgemeinen Formel (I) verwendet werden können, sind im Allgemeinen organische und anorganische Stickstoff-haltige Verbindungen wie beispielsweise Harnstoffe, Hamstoff-Formaldehyd- Kondensationsprodukte, Aminosäuren, Ammoniumsalze und -nitrate, Kaliumsalze (bevorzugt Chloride, Sulfate, Nitrate), Phosphorsäuresalze und/oder Salze von Phosphoriger Säure (bevorzugt Kaliumsalze und Ammoniumsalze). Insbesondere zu nennen sind in diesem Zusammenhang die NPK-Dünger, d.h. Düngemittel, die Stickstoff, Phosphor und Kalium enthalten, Kalkammonsalpeter, d.h. Düngemittel, die noch Calcium enthalten, Ammonsulfatsalpeter (Allgemeine Formel (NH4)2S04 Fertilizers which, according to the invention, can be used together with the compounds of the general formula (I) which are described in more detail below are in general organic and inorganic nitrogen-containing compounds such as, for example, ureas, urea-formaldehyde condensation products, amino acids, ammonium salts and nitrates, Potassium salts (preferably chlorides, sulfates, nitrates), phosphoric acid salts and / or salts of phosphorous acid (preferably potassium salts and ammonium salts). Particularly noteworthy in this connection are NPK fertilizers, ie fertilizers containing nitrogen, phosphorus and potassium, calcium ammonium nitrate, ie fertilizers which still contain calcium, ammonium sulphate nitrate (general formula (NH 4 ) 2 SO 4)
NH4NO3), Ammonphosphat und Ammonsulfat. Diese Düngemittel sind dem Fachmann allgemein bekannt, siehe auch beispielsweise Ullmann's Encyclopedia of Industrial Chemistry, 5. Edition, Vol. A 10, Seiten 323 bis 431 , Verlagsgesellschaft, Weinheim, 1987. NH4NO3), ammonium phosphate and ammonium sulfate. These fertilizers are well known to those skilled in the art, see also, for example, Ullmann's Encyclopedia of Industrial Chemistry, 5th Edition, Vol. A 10, pages 323 to 431, Verlagsgesellschaft, Weinheim, 1987.
Die Düngemittel können auch Salze aus Mikronährstoffen (bevorzugt Calcium, Schwefel, Bor, Mangan, Magnesium, Eisen, Bor, Kupfer, Zink, Molybdän und Kobalt) und Phytohormonen (z. B. Vitamin B1 und Indol-(ll l)essigsäure) oder Gemische davon enthalten. Erfindungsgemäß eingesetzte Düngemittel können auch weitere Salze wie Monoammoniumphosphat (MAP), Diammoniumphosphat (DAP), Kaliumsulfat,The fertilizers may also contain salts of micronutrients (preferably calcium, sulfur, boron, manganese, magnesium, iron, boron, copper, zinc, molybdenum and cobalt) and phytohormones (eg, vitamin B1 and indole (II) acetic acid) or Mixtures thereof included. Fertilizers used according to the invention may also contain other salts such as monoammonium phosphate (MAP), diammonium phosphate (DAP), potassium sulfate,
Kaliumchlorid, Magnesiumsulfat enthalten. Geeignete Mengen für die sekundären Nährstoffe oder Spurenelemente sind Mengen von 0.5 bis 5 Gew.-%, bezogen auf das gesamte Düngemittel. Weitere mögliche Inhaltsstoffe sind Pflanzenschutzmittel, Insektizide oder Fungizide, Wachstumsregulatoren oder Gemische davon. Hierzu folgen weiter unten weitergehende Ausführungen. Containing potassium chloride, magnesium sulfate. Suitable amounts for the secondary nutrients or trace elements are amounts of 0.5 to 5 wt .-%, based on the total fertilizer. Further possible ingredients are crop protection agents, insecticides or fungicides, growth regulators or mixtures thereof. Further explanations follow below.
Die Düngemittel können beispielsweise in Form von Pulvern, Granulaten, Phils oder Kompaktaten eingesetzt werden. Die Düngemittel können jedoch auch in flüssiger Form, gelöst in einem wässrigen Medium, eingesetzt werden. In diesem Fall kann
auch verdünnter wässriger Ammoniak als Stickstoffdüngemittel eingesetzt werden. Weitere mögliche Inhaltsstoffe für Düngemittel sind beispielsweise in Ullmann's Encyclopedia of Industrial Chemistry, 5. Auflage, 1987, Band A 10, Seiten 363 bis 401 , DE-A 41 28 828, DE-A 19 05 834 und DE-A 196 31 764 beschrieben. Die allgemeine Zusammensetzung der Düngemittel, bei welchen es sich im Rahmen der vorliegenden Erfindung um Einzelnährstoff- und/oder Mehrnährstoffdünger handeln kann, beispielsweise aus Stickstoff, Kalium oder Phosphor, kann innerhalb eines breiten Bereichs variieren. Im Allgemeinen ist ein Gehalt von 1 bis 30 Gew.-% Stickstoff (bevorzugt 5 bis 20 Gew.-%), von 1 bis 20 Gew.-% Kalium (bevorzugt 3 bis 15 Gew.- %) und ein Gehalt von 1 bis 20 Gew.-% Phosphor (bevorzugt 3 bis 10 Gew.-%) vorteilhaft. Der Gehalt von Mikroelementen ist üblicherweise im ppm-Bereich, bevorzugt im Bereich von von 1 bis 1000 ppm. The fertilizers can be used, for example, in the form of powders, granules, phils or compactates. However, the fertilizers can also be used in liquid form dissolved in an aqueous medium. In this case can also dilute aqueous ammonia can be used as nitrogen fertilizer. Further possible ingredients for fertilizers are described, for example, in Ullmann's Encyclopedia of Industrial Chemistry, 5th Edition, 1987, Volume A 10, pages 363 to 401, DE-A 41 28 828, DE-A 19 05 834 and DE-A 196 31 764 , The general composition of the fertilizers, which in the context of the present invention may be single nutrient and / or multi-nutrient fertilizers, for example nitrogen, potassium or phosphorus, may vary within a wide range. In general, a content of 1 to 30 wt .-% of nitrogen (preferably 5 to 20 wt .-%), from 1 to 20 wt .-% potassium (preferably 3 to 15% by weight) and a content of 1 to 20% by weight of phosphorus (preferably 3 to 10% by weight) is advantageous. The content of microelements is usually in the ppm range, preferably in the range of from 1 to 1000 ppm.
Im Rahmen der vorliegenden Erfindung können das Düngemittel sowie eine oder mehrere erfindungsgemäße Verbindungen der allgemeinen Formel (I) zeitgleich verabreicht werden. Es ist jedoch auch möglich, zunächst das Düngemittel und dann eine oder mehrere erfindungsgemäße Verbindungen der allgemeinen Formel (I) oder zunächst eine oder mehrere Verbindungen der allgemeinen Formel (I) und dann das Düngemittel anzuwenden. Bei nicht zeitgleicher Anwendung einer oder mehrerer Verbindungen der allgemeinen Formel (I) und des Düngemittels erfolgt im Rahmen der vorliegenden Erfindung jedoch die Anwendung in funktionellem Zusammenhang, insbesondere innerhalb eines Zeitraums von im Allgemeinen 24 Stunden, bevorzugt 18 Stunden, besonders bevorzugt 12 Stunden, speziell 6 Stunden, noch spezieller 4 Stunden, noch weiter spezieller innerhalb 2 Stunden. In ganz besonderen In the context of the present invention, the fertilizer and one or more compounds of the general formula (I) according to the invention can be administered at the same time. However, it is also possible first to apply the fertilizer and then one or more compounds of the general formula (I) according to the invention or first of all one or more compounds of the general formula (I) and then the fertilizer. In the case of non-simultaneous application of one or more compounds of the general formula (I) and of the fertilizer, however, the application is carried out in a functional context, especially within a period of generally 24 hours, preferably 18 hours, more preferably 12 hours, especially 6 hours, more specifically 4 hours, even more special within 2 hours. In a very special way
Ausführungsformen der vorliegenden Erfindung erfolgt die Anwendung einer oder mehrerer erfindungsgemäßer Verbindungen der Formel (I) und des Düngemittels in einem zeitlichen Rahmen von weniger als 1 Stunden, vorzugsweise weniger als 30 Minuten, besonders bevorzugt weniger als 15 Minuten. Bevorzugt ist die Verwendung von Verbindungen der allgemeinen Formel (I) auf Pflanzen aus der Gruppe der Nutzpflanzen, Zierpflanzen, Rasenarten, allgemein genutzte Bäume, die in öffentlichen und privaten Bereichen als Zierpflanzen Embodiments of the present invention use one or more compounds of the formula (I) and the fertilizer according to the invention in a time frame of less than 1 hour, preferably less than 30 minutes, more preferably less than 15 minutes. Preference is given to the use of compounds of the general formula (I) on plants from the group of crops, ornamental plants, lawn species, generally used trees, which are used in ornamental plants in public and private sectors
Verwendungen finden, und Forstbestand. Der Forstbestand umfasst Bäume für die Herstellung von Holz, Zellstoff, Papier und Produkten die aus Teilen der Bäume
hergestellt werden. Der Begriff Nutzpflanzen, wie hier verwendet, bezeichnet Find uses, and forest stands. The forest stock includes trees for the production of wood, pulp, paper and products from parts of the trees getting produced. The term crops as used herein refers to
Kulturpflanzen, die als Pflanzen für die Gewinnung von Nahrungsmitteln, Futtermitteln, Treibstoffe oder für technische Zwecke eingesetzt werden. Zu den Nutzpflanzen zählen z. B. folgende Pflanzenarten: Triticale, Durum Crop plants used as plants for the production of food, feed, fuel or for technical purposes. Among the useful plants include z. For example, the following plant species: Triticale, Durum
(Hartweizen), Turf, Reben, Getreide, beispielsweise Weizen, Gerste, Roggen, Hafer, Reis, Mais und Hirse; Rüben, beispielsweise Zuckerrüben und Futterrüben; Früchte, beispielsweise Kernobst, Steinobst und Beerenobst, beispielsweise Äpfel, Birnen, Pflaumen, Pfirsiche, Mandeln, Kirschen und Beeren, z. B. Erdbeeren, Himbeeren, Brombeeren; Hülsenfrüchte, beispielsweise Bohnen, Linsen, Erbsen und Sojabohnen; Ölkulturen, beispielsweise Raps, Senf, Mohn, Oliven, Sonnenblumen, Kokos, (Durum wheat), turf, vines, cereals, such as wheat, barley, rye, oats, rice, corn and millet; Beets, for example sugar beets and fodder beets; Fruits, such as pome fruit, stone fruit and soft fruit, such as apples, pears, plums, peaches, almonds, cherries and berries, eg. Strawberries, raspberries, blackberries; Legumes, such as beans, lentils, peas and soybeans; Oil crops, such as oilseed rape, mustard, poppy, olives, sunflowers, coconut,
Castorölpflanzen, Kakaobohnen und Erdnüsse; Gurkengewächse, beispielsweise Kürbis, Gurken und Melonen; Fasergewächse, beispielsweise Baumwolle, Flachs, Hanf und Jute; Citrusfrüchte, beispielsweise Orangen, Zitronen, Pampelmusen und Mandarinen; Gemüsesorten, beispielsweise Spinat, (Kopf)-Salat, Spargel, Kohlarten, Möhren, Zwiebeln, Tomaten, Kartoffeln und Paprika; Lorbeergewächse, beispielsweise Avocado, Cinnamomum, Kampfer, oder ebenso Pflanzen wie Tabak, Nüsse, Kaffee, Aubergine, Zuckerrohr, Tee, Pfeffer, Weinreben, Hopfen, Bananen, Castor oil plants, cocoa beans and peanuts; Cucurbits, for example squash, cucumbers and melons; Fiber plants, for example cotton, flax, hemp and jute; Citrus fruits, such as oranges, lemons, grapefruit and mandarins; Vegetables such as spinach, (head) salad, asparagus, cabbages, carrots, onions, tomatoes, potatoes and peppers; Laurel family, such as avocado, cinnamomum, camphor, or plants such as tobacco, nuts, coffee, eggplant, sugar cane, tea, pepper, vines, hops, bananas,
Naturkautschukgewächse sowie Zierpflanzen, beispielsweise Blumen, Sträucher, Laubbäume und Nadelbäume wie Koniferen. Diese Aufzählung stellt keine Limitierung dar. Natural rubber plants and ornamental plants, such as flowers, shrubs, deciduous trees and conifers such as conifers. This list is not a limitation.
Als besonders geeignete Zielkulturen für die Anwendung des erfindungsgemäßen Verfahrens sind folgende Pflanzen anzusehen: Hafer, Roggen, Triticale, Durum, Baumwolle, Aubergine, Turf, Kernobst, Steinobst, Beerenobst, Mais, Weizen, Gerste, Gurke, Tabak, Reben, Reis, Getreide, Birne, Pfeffer, Bohnen, Sojabohnen, Raps, Tomate, Paprika, Melonen, Kohl, Kartoffel und Apfel. Particularly suitable target crops for the application of the method according to the invention are the following plants: oats, rye, triticale, durum, cotton, aubergine, turf, pome fruit, stone fruit, berry fruit, corn, wheat, barley, cucumber, tobacco, vines, rice, cereals , Pear, pepper, beans, soybeans, rape, tomato, paprika, melons, cabbage, potato and apple.
Als Bäume, die entsprechend dem erfindungsgemäßen Verfahren verbessert werden können, seien beispielhaft genannt: Abies sp., Eucalyptus sp., Picea sp., Pinus sp., Aesculus sp., Platanus sp., Tilia sp., Acer sp., Tsuga sp., Fraxinus sp., Sorbus sp., Betula sp., Crataegus sp., Ulmus sp., Quercus sp., Fagus sp., Salix sp., Populus sp..
Als bevorzugte Bäume, die entsprechend dem erfindungsgemäßen Verfahren verbessert werden können, können genannt werden: Aus der Baumart Aesculus: A. hippocastanum, A. pariflora, A. carnea; aus der Baumart Platanus: P. aceriflora, P. occidentalis, P. racemosa; aus der Baumart Picea: P. abies; aus der Baumart Pinus: P. radiate, P. ponderosa, P. contorta, P. sylvestre, P. elliottii, P. montecola, P. Examples of trees which can be improved according to the method of the invention are: Abies sp., Eucalyptus sp., Picea sp., Pinus sp., Aesculus sp., Platanus sp., Tilia sp., Acer sp., Tsuga sp , Fraxinus sp., Sorbus sp., Betula sp., Crataegus sp., Ulmus sp., Quercus sp., Fagus sp., Salix sp., Populus sp. As preferred trees, which can be improved according to the method of the invention, may be mentioned: From the tree species Aesculus: A. hippocastanum, A. pariflora, A. carnea; from the tree species Platanus: P. aceriflora, P. occidentalis, P. racemosa; from the tree species Picea: P. abies; from the tree Pinus: P. radiate, P. ponderosa, P. contorta, P. sylvestre, P. elliottii, P. montecola, P.
albicaulis, P. resinosa, P. palustris, P. taeda, P. flexilis, P. jeffregi, P. baksiana, P. strobes; aus der Baumart Eucalyptus: E. grandis, E. globulus, E. camadentis, E. albicaulis, P. resinosa, P. palustris, P. taeda, P. flexilis, P. jeffregi, P. baksiana, P. strobes; from the tree species Eucalyptus: E. grandis, E. globulus, E. camadentis, E.
nitens, E. obliqua, E. regnans, E. pilularus. Als besonders bevorzugte Bäume, die entsprechend dem erfindungsgemäßen nitens, E. obliqua, E. regnans, E. pilularus. As particularly preferred trees, according to the invention
Verfahren verbessert werden können, können genannt werden: Aus der Baumart Pinus: P. radiate, P. ponderosa, P. contorta, P. sylvestre, P. strobes; aus der Baumart Eucalyptus: E. grandis, E. globulus und E. camadentis. Als besonders bevorzugte Bäume, die entsprechend dem erfindungsgemäßen Methods can be improved can be mentioned: From the tree species Pinus: P. radiate, P. ponderosa, P. contorta, P. sylvestre, P. strobes; from the tree species Eucalyptus: E. grandis, E. globulus and E. camadentis. As particularly preferred trees, according to the invention
Verfahren verbessert werden können, können genannt werden: Rosskastanie, Platanengewächs, Linde und Ahornbaum. Procedures that can be improved include: horse chestnut, sycamore, linden and maple tree.
Die vorliegende Erfindung kann auch an beliebigen Rasenarten („turfgrasses") durchgeführt werden, einschließlich„cool season turfgrasses" und„warm season turfgrasses". Beispiele für Rasenarten für die kalte Jahreszeit sind Blaugräser („blue grasses"; Poa spp.), wie„Kentucky bluegrass" (Poa pratensis L),„rough bluegrass" (Poa trivialis L),„Canada bluegrass" (Poa compressa L),„annual bluegrass" (Poa annua L),„upland bluegrass" (Poa glaucantha Gaudin),„wood bluegrass" (Poa nemoralis L.) und„bulbous bluegrass" (Poa bulbosa L); Straussgräser („Bentgrass", Agrostis spp.), wie„creeping bentgrass" (Agrostis palustris Huds.),„colonial bentgrass" (Agrostis tenuis Sibth.),„velvet bentgrass" (Agrostis canina L),„South German Mixed Bentgrass" (Agrostis spp. einschließlich Agrostis tenius Sibth., Agrostis canina L, und Agrostis palustris Huds.), und„redtop" (Agrostis alba L); The present invention may also be practiced on any turfgrasses, including "cool season turfgrasses" and "warm season turfgrasses." Examples of cold season turf species are blue grasses (Poa spp.), Such as "Kentucky bluegrass" (Poa pratensis L), "rough bluegrass" (Poa trivialis L), "Canada bluegrass" (Poa compressa L), "annual bluegrass" (Poa annua L), "upland bluegrass" (Poa glaucantha Gaudin), "Wood bluegrass" (Poa nemoralis L.) and "bulbous bluegrass" (Poa bulbosa L); ostrich grasses ("Bentgrass", Agrostis spp.), Such as "creeping bentgrass" (Agrostis palustris Huds.), "Colonial bentgrass" (Agrostis Tenuis Sibth.), "velvet bentgrass" (Agrostis canina L), "South German Mixed Bentgrass" (Agrostis spp., including Agrostis tenius Sibth., Agrostis canina L, and Agrostis palustris Huds.), and "redtop" (Agrostis alba L );
Schwingel („Fescues", Festucu spp.), wie„red fescue" (Festuca rubra L. spp. rubra), „creeping fescue" (Festuca rubra L),„chewings fescue" (Festuca rubra commutata Gaud.),„sheep fescue" (Festuca ovina L),„hard fescue" (Festuca longifolia Thuill.),
„hair fescue" (Festucu capillata Lam.),„tali fescue" (Festuca arundinacea Schreb.) und „meadow fescue" (Festuca elanor L); Fescue ("Fescues", Festucu spp.), Such as "red fescue" (Festuca rubra L. spp. Rubra), "creeping fescue" (Festuca rubra L), "chewings fescue" (Festuca rubra commutata Gaud.), "Sheep fescue "(Festuca ovina L)," hard fescue "(Festuca longifolia Thuill.), "Hair fescue" (Festucu capillata Lam.), "Tali fescue" (Festuca arundinacea Schreb.) And "meadow fescue" (Festuca elanor L);
Lolch („ryegrasses", Lolium spp.), wie„annual ryegrass" (Lolium multiflorum Lam.), „perennial ryegrass" (Lolium perenne L.) und„italian ryegrass" (Lolium multiflorum Lam.); und Weizengräser ("wheatgrasses", Agropyron spp..), wie "fairway wheatgrass" (Agropyron cristatum (L.) Gaertn.),„crested wheatgrass" (Agropyron desertorum (Fisch.) Schult.) und "western wheatgrass" (Agropyron smithii Rydb.). Lolium ("ryegrasses", Lolium spp.), Such as "annual ryegrass" (Lolium multiflorum Lam.), "Perennial ryegrass" (Lolium perenne L.) and "Italian ryegrass" (Lolium multiflorum Lam.); and wheat grasses ("wheatgrasses", Agropyron spp.), such as "fairway wheatgrass" (Agropyron cristatum (L.) Gaertn.), "crested wheatgrass" (Agropyron desertorum (fish.) Schult.) and "western wheatgrass" (Agropyron smithii Rydb.).
Beispiele für weitere "cool season turfgrasses" sind "beachgrass" (Ammophila breviligulata Fern.), "smooth bromegrass" (Bromus inermis Leyss.), Schilf ("cattails") wie "Timothy" (Phleum pratense L.), "sand cattail" (Phleum subulatum L.), Examples of other "cool season turfgrasses" are "beachgrass" (Ammophila breviligulata Fern.), "Smooth bromegrass" (Bromus inermis leyss.), Reeds ("cattails") such as "Timothy" (Phleum pratense L.), "sand cattail "(Phleum subulatum L.)
"orchardgrass" (Dactylis glomerata L.), "weeping alkaligrass" (Puccinellia distans (L.) Pari.) und "crested dog's-tail" (Cynosurus cristatus L.). "orchardgrass" (Dactylis glomerata L.), "weeping alkaligrass" (Puccinellia distans (L.) Pari.) and "crested dog's-tail" (Cynosurus cristatus L.).
Beispiele für "warm season turfgrasses" sind„Bermudagrass" (Cynodon spp. L. C. Rieh), "zoysiagrass" (Zoysia spp. Willd.),„St. Augustine grass" (Stenotaphrum secundatum Walt Kuntze),„centipedegrass" (Eremochloa ophiuroides Munro Hack.), „carpetgrass" (Axonopus affinis Chase),„Bahia grass" (Paspalum notatum Flügge), „Kikuyugrass" (Pennisetum clandestinum Höchst, ex Chiov.),„buffalo grass" (Buchloe daetyloids (Nutt.) Engelm.), "Blue gramma" (Bouteloua gracilis (H.B.K.) Lag. ex Griffiths),„seashore paspalum" (Paspalum vaginatum Swartz) und„sideoats grama" (Bouteloua curtipendula (Michx. Torr.). "Cool season turfgrasses" sind für die erfindungsgemäße Verwendung im Allgemeinen bevorzugt. Besonders bevorzugt sind Blaugras, Straussgras und„redtop", Schwingel und Lolch. Straussgras ist Examples of "warm season turfgrasses" are "Bermudagrass" (Cynodon spp., LC Rieh), "zoysiagrass" (Zoysia spp. Willd.), "St. Augustine grass" (Stenotaphrum secundatum Walt Kuntze), "centipedegrass" (Eremochloa ophiuroides Munro Hack.), "Carpetgrass" (Axonopus affinis chase), "Bahia grass" (Paspalum notatum flügge), "Kikuyugrass" (Pennisetum clandestinum Höchst, ex Chiov.), "Buffalo grass" (Buchloe daetyloids (Nutt.) Engelm.) , "Blue gramma" (Bouteloua gracilis (HBK) lag. Ex Griffiths), "seashore paspalum" (Paspalum vaginatum Swartz) and "sideoats grama" (Bouteloua curtipendula (Michx. Torr.). "Cool season turfgrasses" are for the present invention Use is generally preferred Bleach grass, ostrich grass and "redtop", fescue and lolk are particularly preferred
insbesondere bevorzugt. Besonders bevorzugt werden mit den erfindungsgemäßen Verbindungen der allgemeinen Formel (I) Pflanzen der jeweils handelsüblichen oder in Gebrauch befindlichen Pflanzensorten behandelt. Unter Pflanzensorten versteht man Pflanzen mit neuen Eigenschaften ("Traits"), die sowohl durch konventionelle Züchtung, durch M utagenese oder mit Hilfe rekombinanter DNA-Techniken, gezüchtet worden sind.
Kulturpflanzen können demnach Pflanzen sein, die durch konventionelle Züchtungsund Optimierungsmethoden oder durch biotechnologische und gentechnologische Methoden oder Kombinationen dieser Methoden erhalten werden können, einschließlich der transgenen Pflanzen und einschließlich der durch Sortenschutzrechte schützbaren oder nicht schützbaren Pflanzensorten. especially preferred. Particular preference is given to treating the compounds of the general formula (I) according to the invention with plants of the respective commercially available or used plant cultivars. Plant varieties are understood as meaning plants with new traits that have been bred either by conventional breeding, by matagenesis or by recombinant DNA techniques. Crop plants can accordingly be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant varieties which can or can not be protected by plant breeders' rights.
Das erfindungsgemäße Behandlungsverfahren kann somit auch für die Behandlung von genetisch modifizierten Organismen (GMOs), z. B. Pflanzen oder Samen, verwendet werden. Genetisch modifizierte Pflanzen (oder transgene Pflanzen) sind Pflanzen, bei denen ein heterologes Gen stabil in das Genom integriert worden ist. Der Begriff "heterologes Gen" bedeutet im wesentlichen ein Gen, das außerhalb der Pflanze bereitgestellt oder assembliert wird und das bei Einführung in das The treatment method according to the invention can thus also for the treatment of genetically modified organisms (GMOs), z. As plants or seeds are used. Genetically modified plants (or transgenic plants) are plants in which a heterologous gene has been stably integrated into the genome. The term "heterologous gene" essentially means a gene that is provided or assembled outside the plant and that when introduced into the plant
Zellkerngenom, das Chloroplastengenom oder das Hypochondriengenom der transformierten Pflanze dadurch neue oder verbesserte agronomische oder sonstige Eigenschaften verleiht, dass es ein interessierendes Protein oder Polypeptid exprimiert oder dasses ein anderes Gen, das in der Pflanze vorliegt bzw. andere Gene, die in der Pflanze vorliegen, herunterreguliert oder abschaltet (zum Beispiel mittels Antisense- Technologie, Co-suppressionstechnologie oder RNAi-Technologie [RNA Interference]). Ein heterologes Gen, das im Genom vorliegt, wird ebenfalls als Transgen bezeichnet. Ein Transgen, das durch sein spezifisches Vorliegen im Pflanzengenom definiert ist, wird als Transformations- bzw. transgenes Event bezeichnet. Cell nucleus genome, the chloroplast genome or the hypochondrial genome of the transformed plant by conferring new or improved agronomic or other properties by expressing a protein or polypeptide of interest or by having another gene present in the plant or other genes present in the plant; downregulated or switched off (for example by means of antisense technology, co-suppression technology or RNAi technology [RNA Interference]). A heterologous gene present in the genome is also referred to as a transgene. A transgene defined by its specific presence in the plant genome is referred to as a transformation or transgenic event.
Zu Pflanzen und Pflanzensorten, die vorzugsweise mit den erfindungsgemäßen Verbindungen der allgemeinen Formel (I) behandelt werden, zählen alle Pflanzen, die über Erbgut verfügen, das diesen Pflanzen besonders vorteilhafte, nützliche Merkmale verleiht (egal, ob dies durch Züchtung und/oder Biotechnologie erzielt wurde). Plants and plant varieties which are preferably treated with the compounds of the general formula (I) according to the invention include all plants which have genetic material which gives these plants particularly advantageous, useful features (regardless of whether this is achieved by breeding and / or biotechnology has been).
Pflanzen und Pflanzensorten, die ebenfalls mit den erfindungsgemäßen Verbindungen der allgemeinen Formel (I) behandelt werden können, sind solche Pflanzen, die gegen einen oder mehrere abiotische Streßfaktoren resistent sind. Zu den abioti sehen Streßbedingungen können zum Beispiel Hitze, Dürre, Kälte- und Trockenstress., osmotischer Streß, Staunässe, erhöhter Bodensalzgehalt, erhöhtes Ausgesetztsein an Mineralien, Ozonbedingungen, Starklichtbedingungen, beschränkte Verfügbarkeit von
Stickstoffnährstoffen, beschränkte Verfügbarkeit von Phosphornährstoffen oder Vermeidung von Schatten zählen. Plants and plant varieties which can also be treated with the compounds of the general formula (I) according to the invention are those plants which are resistant to one or more abiotic stress factors. The abiotic stress conditions may include, for example, heat, drought, cold and dry stress, osmotic stress, waterlogging, increased soil salt content, increased exposure to minerals, ozone conditions, high light conditions, limited availability of Nitrogen nutrients, limited availability of phosphorus nutrients or avoiding shadows.
Pflanzen und Pflanzensorten, die ebenfalls mit den erfindungsgemäßen Verbindungen der allgemeinen Formel (I) behandelt werden können, sind solche Pflanzen, die durch erhöhte Ertragseigenschaften gekennzeichnet sind. Ein erhöhter Ertrag kann bei diesen Pflanzen z. B. auf verbesserter Pflanzenphysiologie, verbessertem Plants and plant varieties which can also be treated with the compounds of the general formula (I) according to the invention are those plants which are characterized by increased yield properties. An increased yield can in these plants z. B. on improved plant physiology, improved
Pflanzenwuchs und verbesserter Pflanzenentwicklung, wie Plant growth and improved plant development, such as
Wasserverwertungseffizienz, Wasserhalteeffizienz, verbesserter Stickstoffverwertung, erhöhter Kohlenstoffassimilation, verbesserter Photosynthese, verstärkter Keimkraft und beschleunigter Abreife beruhen. Der Ertrag kann weiterhin durch eine verbesserte Pflanzenarchitektur (unter Streß- und nicht-Streß-Bedingungen) beeinflußt werden, darunter frühe Blüte, Kontrolle der Blüte für die Produktion von Hybridsaatgut, Keimpflanzenwüchsigkeit, Pflanzengröße, Internodienzahl und -abstand, Water utilization efficiency, water retention efficiency, improved nitrogen utilization, increased carbon assimilation, improved photosynthesis, increased germination power and accelerated Abreife based. Yield can be further influenced by improved plant architecture (under stress and non-stress conditions), including early flowering, control of flowering for hybrid seed production, seedling vigor, plant size, internode count and distance,
Wurzelwachstum, Samengröße, Fruchtgröße, Schotengröße, Schoten- oder Root growth, seed size, fruit size, pod size, pods or
Ährenzahl, Anzahl der Samen pro Schote oder Ähre, Samenmasse, verstärkte Samenfüllung, verringerter Samenausfall, verringertes Schotenplatzen sowie Ear number, number of seeds per pod or ear, seed mass, increased seed filling, reduced seed drop, reduced pod popping as well
Standfestigkeit. Zu weiteren Ertragsmerkmalen zählen Samenzusammensetzung wie Kohlenhydratgehalt, Proteingehalt, ölgehalt und ölzusammensetzung, Nährwert, Verringerung der nährwidrigen Verbindungen, verbesserte Verarbeitbarkeit und verbesserte Lagerfähigkeit. Stability. Other yield-related traits include seed composition such as carbohydrate content, protein content, oil content and oil composition, nutritional value, reduction in nontoxic compounds, improved processability, and improved shelf life.
Pflanzen, die ebenfalls mit den erfindungsgemäßen Verbindungen der allgemeinen Formel (I) behandelt werden können, sind Hybridpflanzen, die bereits die Plants which can also be treated with the compounds of the general formula (I) according to the invention are hybrid plants which have already been used
Eigenschaften der Heterosis bzw. des Hybrideffekts exprimieren, was im allgemeinen zu höherem Ertrag, höherer Wüchsigkeit, besserer Gesundheit und besserer Characteristics of heterosis or hybrid effect, which generally results in higher yield, higher vigor, better health and better
Resistenz gegen biotische und abiotische Streßfaktoren führt. Solche Pflanzen werden typischerweise dadurch erzeugt, dass man eine ingezüchtete pollensterile Elternlinie (den weiblichen Kreuzungspartner) mit einer anderen ingezüchteten pollenfertilen Elternlinie (dem männlichen Kreuzungspartner) kreuzt. Das Hybridsaatgut wird typischerweise von den pollensterilen Pflanzen geerntet und an Vermehrer verkauft. Pollensterile Pflanzen können manchmal (z. B. beim Mais) durch Entfahnen (d. h. mechanischem Entfernen der männlichen Geschlechtsorgane bzw. der männlichen Blüten), produziert werden; es ist jedoch üblicher, dass die Pollensterilität auf
genetischen Determinanten im Pflanzengenom beruht. In diesem Fall, insbesondere dann, wenn es sich bei dem gewünschten Produkt, da man von den Hybridpfianzen ernten will, um die Samen handelt, ist es üblicherweise günstig, sicherzustellen, dass die Pollenfertilität in Hybridpflanzen, die die für die Pollensterilität verantwortlichen genetischen Determinanten enthalten, völlig restoriert wird. Dies kann erreicht werden, indem sichergestellt wird, dass die männlichen Kreuzungspartner entsprechende Fertilitätsrestorergene besitzen, die in der Lage sind, die Pollenfertilität in Resistance to biotic and abiotic stress factors leads. Such plants are typically produced by crossing an inbred male sterile parental line (the female crossover partner) with another inbred male fertile parent line (the male crossbred partner). The hybrid seed is typically harvested from the male sterile plants and sold to propagators. Pollen sterile plants can sometimes be produced (eg in maize) by delaving (ie mechanical removal of the male reproductive organs or the male flowers); However, it is more common for the pollen sterility to genetic determinants in the plant genome. In this case, especially when the desired product, as one wants to harvest from the hybrid crops, is the seeds, it is usually beneficial to ensure that the pollen fertility in hybrid plants containing the genetic determinants responsible for male sterility , completely restored. This can be accomplished by ensuring that the male crossbred partners possess appropriate fertility restorer genes capable of controlling pollen fertility in humans
Hybridpflanzen, die die genetischen Determinanten, die für die Pollensterilität verantwortlich sind, enthalten, zu restorieren. Genetische Determinanten für Hybrid plants that contain the genetic determinants responsible for male sterility. Genetic determinants for
Pollensterilität können im Cytoplasma lokalisiert sein. Beispiele für cytoplasmatische Pollensterilität (CMS) wurden zum Beispiel für Brassica-Arten beschrieben (WO 92/005251 . WO 95/009910, WO 98/27806, WO 05/002324, WO 06/021972 und US 6.229,072). Genetische Determinanten für Pollensterilität können jedoch auch im Zellkerngenom lokalisiert sein. Pollensterile Pflanzen können auch mit Methoden der pflanzlichen Biotechnologie, wie Gentechnik, erhalten werden. Ein besonders günstiges Mittel zur Erzeugung von pollensterilen Pflanzen ist in WO 89/10396 beschrieben, wobei zum Beispiel eine Ribonuklease wie eine Barnase selektiv in den Tapetumzellen in den Staubblättern exprimiert wird. Die Fertilität kann dann durch Expression eines Ribonukleasehemmers wie Barstar in den Tapetumzellen restoriert werden (z. B. WO 91/002069). Pollen sterility may be localized in the cytoplasm. Examples of cytoplasmic male sterility (CMS) have been described, for example, for Brassica species (WO 92/005251, WO 95/009910, WO 98/27806, WO 05/002324, WO 06/021972 and US 6,229,072). However, genetic determinants of pollen sterility may also be localized in the nuclear genome. Pollen sterile plants can also be obtained using plant biotechnology methods such as genetic engineering. A particularly convenient means of producing male-sterile plants is described in WO 89/10396, wherein, for example, a ribonuclease such as a barnase is selectively expressed in the tapetum cells in the stamens. The fertility can then be restorated by expression of a ribonuclease inhibitor such as barstar in the tapetum cells (eg WO 91/002069).
Pflanzen oder Pflanzensorten (die mit Methoden der Pflanzenbiotechnologie, wie der Gentechnik, erhalten werden), die ebenfalls mit den erfindungsgemäßen Plants or plant varieties (which are obtained by plant biotechnology methods, such as genetic engineering), which also with the inventive
Verbindungen der allgemeinen Formel (I) behandelt werden können, sind Compounds of general formula (I) can be treated are
herbizidtolerante Pflanzen, d. h. Pflanzen, die gegenüber einem oder mehreren vorgegebenen Herbiziden tolerant gemacht worden sind. Solche Pflanzen können entweder durch genetische Transformation oder durch Selektion von Pflanzen, die eine Mutation enthalten, die solch eine Herbizidtoleranz verleiht, erhalten werden. Herbizidtolerante Pflanzen sind zum Beispiel glyphosatetolerante Pflanzen, d. h. herbicide-tolerant plants, d. H. Plants tolerant to one or more given herbicides. Such plants can be obtained either by genetic transformation or by selection of plants containing a mutation conferring such herbicide tolerance. Herbicide-tolerant plants are, for example, glyphosate-tolerant plants, i. H.
Pflanzen, die gegenüber dem Herbizid Glyphosate oder dessen Salzen tolerant gemacht worden sind. So können zum Beispiel glyphosatetolerante Pflanzen durch Transformation der Pflanze mit einem Gen, das für das Enzym 5-Enolpyruvylshikimat- 3-phosphatsynthase (EPSPS) kodiert, erhalten werden. Beispiele für solche EPSPS-
Gene sind das AroA-Gen (Mutante CT7) des Bakterium Salmonella typhimurium (Comai et al., Science (1983), 221 , 370-371 ), das CP4-Gen des Bakteriums Plants tolerant to the herbicide glyphosate or its salts. For example, glyphosate-tolerant plants can be obtained by transforming the plant with a gene encoding the enzyme 5-enolpyruvylshikimate-3-phosphate synthase (EPSPS). Examples of such EPSPS Genes are the AroA gene (mutant CT7) of the bacterium Salmonella typhimurium (Comai et al., Science (1983), 221, 370-371), the CP4 gene of the bacterium
Agrobacterium sp. (Barry et al., Curr. Topics Plant Physiol. (1992), 7, 139-145), die Gene, die für eine EPSPS aus der Petunie (Shah et al., Science (1986), 233, 478- 481 ), für eine EPSPS aus der Tomate (Gasser et al., J. Biol. Chem. (1988), 263, 4280- 4289) oder für eine EPSPS aus Eleusine (WO 01/66704) kodieren. Es kann sich auch um eine mutierte EPSPS handeln, wie sie zum Beispiel in EP-A 0837944, WO Agrobacterium sp. (Barry et al., Curr Topics Plant Physiol. (1992), 7, 139-145), the genes responsible for petunia EPSPS (Shah et al., Science (1986), 233, 478-481). , for a EPSPS from the tomato (Gasser et al., J. Biol. Chem. (1988), 263, 4280- 4289) or for an EPSPS from Eleusine (WO 01/66704) encode. It may also be a mutated EPSPS, as described for example in EP-A 0837944, WO
00/066746, WO 00/066747 oder WO 02/026995 beschrieben ist. Glyphosatetolerante Pflanzen können auch dadurch erhalten werden, dass man ein Gen exprimiert, das für ein Glyphosate-Oxidoreduktase-Enzym, wie es in US 5,776,760 und US 5.463, 175 beschrieben ist, kodiert. Glyphosatetolerante Pflanzen können auch dadurch erhalten werden, dass man ein Gen exprimiert, das für ein Glyphosate-acetyltransferase- Enzym, wie es in z. B. WO 02/036782, WO 03/092360, WO 05/012515 und WO 07/024782 beschrieben ist, kodiert. Glyphosatetolerante Pflanzen können auch dadurch erhalten werden, dass man Pflanzen, die natürlich vorkommende Mutationen der oben erwähnten Gene, wie sie zum Beispiel in WO 01/024615 oder WO 00/066746, WO 00/066747 or WO 02/026995. Glyphosate-tolerant plants can also be obtained by expressing a gene coding for a glyphosate oxidoreductase enzyme as described in US 5,776,760 and US 5,463,175. Glyphosate-tolerant plants may also be obtained by expressing a gene encoding a glyphosate acetyltransferase enzyme as described in, e.g. WO 02/036782, WO 03/092360, WO 05/012515 and WO 07/024782. Glyphosate-tolerant plants can also be obtained by culturing plants containing the naturally occurring mutations of the above-mentioned genes, as described, for example, in WO 01/024615 or WO
03/013226 beschrieben sind, enthalten, selektiert. 03/013226 are described, contained, selected.
Sonstige herbizidresistente Pflanzen sind zum Beispiel Pflanzen, die gegenüber Herbiziden, die das Enzym Glutaminsynthase hemmen, wie Biaiaphos, Phosphinotricin oder Glufosinate, tolerant gemacht worden sind. Solche Pflanzen können dadurch erhalten werden, dass man ein Enzym exprimiert, das das Herbizid oder eine Mutante des Enzyms Glutaminsynthase, das gegenüber Hemmung resistent ist, entgiftet. Solch ein wirksames entgiftendes Enzym ist zum Beispiel ein Enzym, das für ein Other herbicide-resistant plants are, for example, plants which have been tolerated to herbicides which inhibit the enzyme glutamine synthase, such as biaiaphos, phosphinotricin or glufosinate. Such plants can be obtained by expressing an enzyme which detoxifies the herbicide or a mutant of the enzyme glutamine synthase, which is resistant to inhibition. Such an effective detoxifying enzyme is, for example, an enzyme suitable for
Phosphinotricin-acetyltransferase kodiert (wie zum Beispiel das bar- oder pat-Protein aus Streptomyces-Arten). Pflanzen, die eine exogene Phosphinotricin- acetyltransferase exprimieren, sind zum Beispiel in US 5,561 .236; US 5.648,477; US 5.646,024; US 5,273.894; US 5,637,489; US 5.276,268; US 5,739,082; US 5.908,810 und US 7,1 12,665 beschrieben. Phosphinotricin acetyltransferase encoded (such as the bar or pat protein from Streptomyces species). Plants expressing an exogenous phosphinotricin acetyltransferase are described, for example, in US 5,561,236; US 5,648,477; US 5,646,024; US 5,273,894; US 5,637,489; US 5,276,268; US 5,739,082; US 5,908,810 and US 7,112,665.
Weitere herbizidtolerante Pflanzen sind auch Pflanzen, die gegenüber den Herbiziden, die das Enzym Hydroxyphenylpyruvatdioxygenase (HPPD) hemmen, tolerant gemacht worden sind. Bei den Hydroxyphenylpyruvatdioxygenasen handelt es sich um Enzyme, die die Reaktion, in der para-Hydroxyphenylpyruvat (HPP) zu Homogentisat umgesetzt
wird, katalysieren. Pflanzen, die gegenüber HPPD-Hemmern tolerant sind, können mit einem Gen, das für ein natürlich vorkommendes resistentes HPPD-Enzym kodiert, oder einem Gen, das für ein mutiertes HPPD-Enzym gemäß WO 96/038567, WO 99/024585 und WO 99/024586 kodiert, transformiert werden. Eine Toleranz gegenüber HPPD-Hemmern kann auch dadurch erzielt werden, dass man Pflanzen mit Genen transformiert, die für gewisse Enzyme kodieren, die die Bildung von Homogentisat trotz Hemmung des nativen HPPD-Enzyms durch den HPPD-Hemmer ermöglichen. Solche Pflanzen und Gene sind in WO 99/034008 und WO 2002/36787 beschrieben. Die Toleranz von Pflanzen gegenüber HPPD-Hemmern kann auch dadurch verbessert werden, dass man Pflanzen zusätzlich zu einem Gen, das für ein HPPD-tolerantes Enzym kodiert, mit einem Gen transformiert, das für ein Prephenatdehydrogenase- Enzym kodiert, wie dies in WO 2004/024928 beschrieben ist. Further herbicide-tolerant plants are also plants tolerant to the herbicides which inhibit the enzyme hydroxyphenylpyruvate dioxygenase (HPPD). The hydroxyphenylpyruvate dioxygenases are enzymes that convert the reaction in which para-hydroxyphenylpyruvate (HPP) into homogentisate will catalyze. Plants tolerant of HPPD inhibitors may be treated with a gene encoding a naturally occurring resistant HPPD enzyme, or a gene encoding a mutant HPPD enzyme as described in WO 96/038567, WO 99/024585 and WO 99/1998 / 024586, are transformed. Tolerance to HPPD inhibitors can also be achieved by transforming plants with genes encoding certain enzymes that allow the formation of homogentisate despite inhibition of the native HPPD enzyme by the HPPD inhibitor. Such plants and genes are described in WO 99/034008 and WO 2002/36787. The tolerance of plants to HPPD inhibitors can also be improved by transforming plants, in addition to a gene which codes for an HPPD-tolerant enzyme, with a gene which codes for a prephenate dehydrogenase enzyme, as described in WO 2004 / 024928 is described.
Weitere herbizidresistente Pflanzen sind Pflanzen, die gegenüber Acetolactatsynthase (ALS)-Hemmern tolerant gemacht worden sind. Zu bekannten ALS-Hemmern zählen zum Beispiel Sulfonylharnstoff, Imidazolinon, Triazolopyrimidine, Other herbicide-resistant plants are plants that have been tolerated to acetolactate synthase (ALS) inhibitors. Examples of known ALS inhibitors include sulfonylurea, imidazolinone, triazolopyrimidines,
Pyrimidinyloxy(thio)benzoate und/oder Sulfonylaminocarbonyltriazolinon-Herbizide. Es ist bekannt, dass verschiedene Mutationen im Enzym ALS (auch als Pyrimidinyloxy (thio) benzoates and / or sulfonylaminocarbonyltriazolinone herbicides. It is known that various mutations in the enzyme ALS (also known as
Acetohydroxysäure-Synthase, AHAS, bekannt) eine Toleranz gegenüber Acetohydroxy acid synthase, AHAS, known) a tolerance to
unterschiedlichen Herbiziden bzw. Gruppen von Herbiziden verleihen, wie dies zum Beispiel bei Tranel und Wright, Weed Science (2002), 50, 700-712, jedoch auch in US 5,605,01 1 , US 5,378.824, US 5,141 .870 und US 5,013.659, beschrieben ist. Die Herstellung von sulfonylharnstofftoleranten Pflanzen und imidazolinontoleranten Pflanzen ist in US 5,605,01 1 ; US 5,013.659; US 5.141 ,870; US 5,767,361 ; US different herbicides or groups of herbicides, as described, for example, by Tranel and Wright, Weed Science (2002), 50, 700-712, but also in US Pat. Nos. 5,605,011, 5,378,824, 5,141,870 and 5,013,659. is described. The preparation of sulfonylurea tolerant plants and imidazolinone tolerant plants is described in US 5,605,011 1; US 5,013,659; US 5,141,870; US 5,767,361; US
5,731 .180; US 5,304,732; US 4,761 .373; US 5,331 ,107; US 5,928,937; und US5,731,180; US 5,304,732; US 4,761,373; US 5,331, 107; US 5,928,937; and US
5.378,824; sowie in der internationalen Veröffentlichung WO 96/033270 beschrieben. Weitere imidazolinontolerante Pflanzen sind auch in z. B. WO 2004/040012, WO 2004/106529, WO 2005/020673, WO 2005/093093, WO 2006/007373, WO 5378.824; and in international publication WO 96/033270. Other imidazolinontolerante plants are also in z. WO 2004/040012, WO 2004/106529, WO 2005/020673, WO 2005/093093, WO 2006/007373, WO
2006/015376, WO 2006/024351 und WO 2006/060634 beschrieben. Weitere 2006/015376, WO 2006/024351 and WO 2006/060634. Further
Sulfonylharnstoff- und imidazolinontolerante Pflanzen sind auch in z.B. WO Sulfonylurea and imidazolinone tolerant plants are also useful in e.g. WHERE
2007/024782 beschrieben. 2007/024782 described.
Weitere Pflanzen, die gegenüber ALS-Inhibitoren, insbesondere gegenüber Other plants that are resistant to ALS inhibitors, especially against
Imidazolinonen, Sulfonylharnstoffen und/oder Sulfamoylcarbonyltriazolinonen tolerant
sind, können durch induzierte Mutagenese, Selektion in Zellkulturen in Gegenwart des Herbizids oder durch Mutationszüchtung erhalten werden, wie dies zum Beispiel für die Sojabohne in US 5.084,082, für Reis in WO 97/41218, für die Zuckerrübe in US 5,773,702 und WO 99/057965, für Salat in US 5,198,599 oder für die Sonnenblume in WO 2001 /065922 beschrieben ist. Imidazolinones, sulfonylureas and / or sulfamoylcarbonyltriazolinones tolerant can be obtained by induced mutagenesis, selection in cell cultures in the presence of the herbicide or by mutation breeding, as for example for the soybean in US 5,084,082, for rice in WO 97/41218, for the sugar beet in US 5,773,702 and WO 99 / 057965, for salad in US 5,198,599 or for the sunflower in WO 2001/065922.
Pflanzen oder Pflanzensorten (die nach Methoden der pflanzlichen Biotechnologie, wie der Gentechnik, erhalten wurden), die ebenfalls mit den erfindungsgemäßen Plants or plant varieties (obtained by plant biotechnology methods, such as genetic engineering), which are also with the inventive
Verbindungen der allgemeinen Formel (I) behandelt werden können, sind Compounds of general formula (I) can be treated are
insektenresistente transgene Pflanzen, d.h. Pflanzen, die gegen Befall mit gewissen Zielinsekten resistent gemacht wurden. Solche Pflanzen können durch genetische Transformation oder durch Selektion von Pflanzen, die eine Mutation enthalten, die solch eine Insektenresistenz verleiht, erhalten werden. Der Begriff "insektenresistente transgene Pflanze" umfaßt im vorliegenden insect-resistant transgenic plants, i. Plants that have been made resistant to attack by certain target insects. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such insect resistance. The term "insect-resistant transgenic plant" as used herein
Zusammenhang jegliche Pflanze, die mindestens ein Transgen enthält, das eine Kodiersequenz umfaßt, die für folgendes kodiert: Relates to any plant containing at least one transgene comprising a coding sequence coding for:
1 ) ein Insektizides Kristallprotein aus Bacillus thuringiensis oder einen Insektiziden Teil davon, wie die Insektiziden Kristallproteine, die von Crickmore et al., Microbiology and Molecular Biology Reviews (1998), 62, 807-813, zusammengestellt wurden, von Crickmore et al. (2005) in der Bacillus thuringiensis-Toxinnomenklatur aktualisiert (online bei: 1) an insecticidal crystal protein from Bacillus thuringiensis or an insecticidal portion thereof, such as the insecticidal crystal proteins collected by Crickmore et al., Microbiology and Molecular Biology Reviews (1998), 62, 807-813, by Crickmore et al. (2005) in the Bacillus thuringiensis toxin nomenclature (online at:
http://www.lifesci.sussex.ac.uk/Home/Neil_Crickmore/Bt/), oder Insektizide Teile davon, z.B. Proteine der Cry-Proteinklassen Cry1 Ab, Cry1 Ac, Cry1 F, Cry2Ab, Cry3Ae oder Cry3Bb oder insektizide Teile davon; oder http://www.lifesci.sussex.ac.uk/Home/Neil_Crickmore/Bt/), or insecticidal parts thereof, e.g. Proteins of Cry protein classes Cry1 Ab, Cry1 Ac, Cry1 F, Cry2Ab, Cry3Ae or Cry3Bb or insecticidal parts thereof; or
2) ein Kristallprotein aus Bacillus thuringiensis oder einen Teil davon, der in Gegenwart eines zweiten, anderen Kristallproteins als Bacillus thuringiensis oder eines Teils davon insektizid wirkt, wie das binäre Toxin, das aus den Kristallproteinen Cy34 und Cy35 besteht (Moellenbeck et al., Nat. Biotechnol. (2001 ), 19, 668-72; Schnepf et al., Applied Environm. Microb. (2006), 71 , 1765-1774); oder
3) ein Insektizides Hybridprotein, das Teile von zwei unterschiedlichen Insektiziden Kristallproteinen aus Bacillus thuringiensis umfaßt, wie zum Beispiel ein Hybrid aus den Proteinen von 1 ) oben oder ein Hybrid aus den Proteinen von 2) oben, z. B. das Protein Cry1 A.105, das von dem Mais-Event MON98034 produziert wird (WO 2) a crystal protein from Bacillus thuringiensis or a part thereof which is insecticidal in the presence of a second, different crystal protein than Bacillus thuringiensis or a part thereof, such as the binary toxin consisting of the crystal proteins Cy34 and Cy35 (Moellenbeck et al., Nat Biotechnol. (2001), 19, 668-72; Schnepf et al., Applied Environment Microb. (2006), 71, 1765-1774); or 3) an insecticidal hybrid protein comprising parts of two different insecticides of Bacillus thuringiensis crystal proteins, such as a hybrid of the proteins of 1) above or a hybrid of the proteins of 2) above, e.g. For example, the protein Cry1 A.105 produced by the corn event MON98034 (WO
2007/027777); oder 2007/027777); or
4) ein Protein gemäß einem der Punkte 1 ) bis 3) oben, in dem einige, 4) a protein according to any one of items 1) to 3) above, in which some,
insbesondere 1 bis 10, Aminosäuren durch eine andere Aminosäure ersetzt wurden, um eine höhere Insektizide Wirksamkeit gegenüber einer Zielinsektenart zu erzielen und/oder um das Spektrum der entsprechenden Zielinsektenarten zu erweitern und/oder wegen Veränderungen, die in die Kodier- DNA während der Kionierung oder Transformation induziert wurden, wie das Protein Cry3Bb1 in Mais-Events MON863 oder MON88017 oder das Protein Cry3A im Mais-Event MIR 604; oder In particular, 1 to 10, amino acids have been replaced by another amino acid to achieve higher insecticidal activity against a target insect species and / or to broaden the spectrum of the corresponding target insect species and / or due to changes in the coding DNA during the cationization or Transformation were induced, such as the protein Cry3Bb1 in maize events MON863 or MON88017 or the protein Cry3A in the maize event MIR 604; or
5) ein Insektizides sezerniertes Protein aus Bacillus thuringiensis oder Bacillus cereus oder einen Insektiziden Teil davon, wie die vegetativ wirkenden 5) an insecticidal secreted protein from Bacillus thuringiensis or Bacillus cereus or an insecticidal part thereof, such as the vegetative
insektentoxischen Proteine (vegetative insecticidal proteins, VIP), die unter folgendem Link angeführt sind, z. B. Proteine der Proteinklasse VIP3Aa: insecticidal proteins (VIP) listed under the following link, e.g. B. Proteins of protein class VIP3Aa:
http://www.lifesci.sussex.ac.uk/Home/Neil_Crickmore/Bt/vip.html oder http://www.lifesci.sussex.ac.uk/Home/Neil_Crickmore/Bt/vip.html or
6) ein sezerniertes Protein aus Bacillus thuringiensis oder Bacillus cereus, das in Gegenwart eines zweiten sezernierten Proteins aus Bacillus thuringiensis oder B. cereus insektizid wirkt, wie das binäre Toxin, das aus den Proteinen VIP1A und VIP2A besteht (WO 94/21795); oder 6) a secreted protein from Bacillus thuringiensis or Bacillus cereus which is insecticidal in the presence of a second secreted protein from Bacillus thuringiensis or B. cereus, such as the binary toxin consisting of the proteins VIP1A and VIP2A (WO 94/21795); or
7) ein Insektizides Hybridprotein, das Teile von verschiedenen sezernierten Proteinen von Bacillus thuringiensis oder Bacillus cereus umfaßt, wie ein Hybrid der Proteine von 1 ) oder ein Hybrid der Proteine von 2) oben; oder 8) ein Protein gemäß einem der Punkte 1 ) bis 3) oben, in dem einige, 7) an insecticidal hybrid protein comprising parts of various secreted proteins of Bacillus thuringiensis or Bacillus cereus, such as a hybrid of the proteins of 1) or a hybrid of the proteins of 2) above; or 8) a protein according to any one of items 1) to 3) above, in which some,
insbesondere 1 bis 10, Aminosäuren durch eine andere Aminosäure ersetzt wurden, um eine höhere Insektizide Wirksamkeit gegenüber einer Zielinsektenart zu erzielen und/oder um das Spektrum der entsprechenden Zielinsektenarten zu erweitern und/oder wegen Veränderungen, die in die Kodier- DNA während der Kionierung oder
Transformation induziert wurden (wobei die Kodierung für ein Insektizides Protein erhalten bleibt), wie das Protein VIP3Aa im Baumwoll-Event COT 102. In particular, 1 to 10, amino acids have been replaced by another amino acid to achieve higher insecticidal activity against a target insect species and / or to broaden the spectrum of the corresponding target insect species and / or due to changes in the coding DNA during the cationization or Transformation (retaining coding for an insecticidal protein) such as protein VIP3Aa in cotton event COT 102.
Natürlich zählt zu den insektenresistenten transgenen Pflanzen im vorliegenden Zusammenhang auch jegliche Pflanze, die eine Kombination von Genen umfaßt, die für die Proteine von einer der oben genannten Klassen 1 bis 8 kodieren. In einer Ausführungsform enthält eine insektenresistente Pflanze mehr als ein Transgen, das für ein Protein nach einer der oben genannten 1 bis 8 kodiert, um das Spektrum der entsprechenden Zielinsektenarten zu erweitern oder um die Entwicklung einer Resistenz der Insekten gegen die Pflanzen dadurch hinauszuzögern, dass man verschiedene Proteine einsetzt, die für dieselbe Zielinsektenart insektizid sind, jedoch eine unterschiedliche Wirkungsweise, wie Bindung an unterschiedliche Of course, insect-resistant transgenic plants in the present context also include any plant comprising a combination of genes encoding the proteins of any of the above classes 1 to 8. In one embodiment, an insect resistant plant contains more than one transgene encoding a protein of any one of the above 1 to 8 in order to extend the spectrum of the corresponding target insect species or to delay the development of resistance of the insects to the plants by use different proteins which are insecticidal for the same target insect species, but a different mode of action, such as binding to different ones
Rezeptorbindungsstellen im Insekt, aufweisen. Pflanzen oder Pflanzensorten (die nach Methoden der pflanzlichen Biotechnologie, wie der Gentechnik, erhalten wurden), die ebenfalls mit den erfindungsgemäßen Receptor binding sites in the insect. Plants or plant varieties (obtained by plant biotechnology methods, such as genetic engineering), which are also with the inventive
Verbindungen der allgemeinen Formel (I) behandelt werden können, sind gegenüber abioti sehen Streßfaktoren tolerant. Solche Pflanzen können durch genetische Compounds of general formula (I) are tolerant to abiotic stress factors. Such plants can be caused by genetic
Transformation oder durch Selektion von Pflanzen, die eine Mutation enthalten, die solch eine Streßresistenz verleiht, erhalten werden. Zu besonders nützlichen Pflanzen mit Streßtoleranz zählen folgende: a. Pflanzen, die ein Transgen enthalten, das die Expression und/oder Aktivität des Gens für die Poly(ADP-ribose)polymerase (PARP) in den Pflanzenzellen oder Pflanzen zu reduzieren vermag, wie dies in WO 2000/004173 oder EP 04077984.5 oder EP 06009836.5 beschrieben ist. b. Pflanzen, die ein streßtoleranzförderndes Transgen enthalten, das die Transformation or by selection of plants containing a mutation conferring such stress resistance. Particularly useful plants with stress tolerance include the following: a. Plants which contain a transgene capable of reducing the expression and / or activity of the gene for the poly (ADP-ribose) polymerase (PARP) in the plant cells or plants, as described in WO 2000/004173 or EP 04077984.5 or EP 06009836.5 is described. b. Plants containing a stress tolerance-enhancing transgene which causes the
Expression und/oder Aktivität der für PARG kodierenden Gene der Pflanzen oder Pflanzenzellen zu reduzieren vermag, wie dies z.B. in WO 2004/090140 beschrieben ist; c. Pflanzen, die ein streßtoleranzförderndes Transgen enthalten, das für ein in Pflanzen funktionelles Enzym des Nicotinamidadenindinukleotid-Salvage-
Biosynthesewegs kodiert, darunter Nicotinamidase, Can reduce expression and / or activity of PARG encoding genes of plants or plant cells, as described for example in WO 2004/090140; c. Plants containing a stress tolerance enhancing transgene useful for a plant functional enzyme of nicotinamide adenine dinucleotide salvage Biosynthetic pathway, including nicotinamidase,
Nicotinatphosphoribosyltransferase, Nicotinsäuremononukleotid-adenyltransferase, Nicotinamidadenindinukleotidsynthetase oder Nicotinamidphosphoribosyi-transferase, wie dies z. B. in EP 04077624.7 oder WO 2006/133827 oder PCT/EP07/002433 beschrieben ist. Nicotinate phosphoribosyltransferase, nicotinic acid mononucleotide adenyltransferase, nicotinamide adenine dinucleotide synthetase, or nicotinamide phosphoribosyltransferase as described e.g. As described in EP 04077624.7 or WO 2006/133827 or PCT / EP07 / 002433.
Pflanzen oder Pflanzensorten (die nach Methoden der pflanzlichen Biotechnologie, wie der Gentechnik, erhalten wurden), die ebenfalls mit den erfindungsgemäßen Plants or plant varieties (obtained by plant biotechnology methods, such as genetic engineering), which are also with the inventive
Verbindungen der allgemeinen Formel (I) behandelt werden können, weisen eine veränderte Menge, Qualität und/oder Lagerfähigkeit des Ernteprodukts und/oder veränderte Eigenschaften von bestimmten Bestandteilen des Ernteprodukts auf, wie zum Beispiel: Compounds of general formula (I) may have an altered amount, quality and / or shelf life of the crop and / or altered properties of certain components of the crop, such as:
1 ) Transgene Pflanzen, die eine modifizierte Stärke synthetisieren, die bezüglich ihrer chemisch-physikalischen Eigenschaften, insbesondere des Amylosegehalts oder des Amylose/Amylopektin-Verhältnisses, des Verzweigungsgrads, der 1) Transgenic plants that synthesize a modified starch, with respect to their chemical-physical properties, in particular the amylose content or the amylose / amylopectin ratio, the degree of branching, the
durchschnittlichen Kettenlänge, der Verteilung der Seitenketten, des average chain length, the distribution of side chains, the
Viskositätsverhaltens, der Gelfestigkeit, der Stärkekorngröße und/oder Viscosity behavior, the gel strength, the starch grain size and / or
Stärkekornmorphologie im Vergleich mit der synthetisierten Stärke in Starch grain morphology in comparison with the synthesized starch in
Wildtyppflanzenzellen oder -pflanzen verändert ist, so dass sich diese modifizierte Stärke besser für bestimmte Anwendungen eignet. Diese transgenen Pflanzen, die eine modifizierte Stärke synthetisieren, sind zum Beispiel in EP 0571427, Wild-type plant cells or plants, so that this modified starch is better suited for certain applications. These transgenic plants which synthesize a modified starch are described, for example, in EP 0571427,
WO 95/004826, EP 0719338, WO 96/15248, WO 96/19581 , WO 96/27674, WO 95/004826, EP 0719338, WO 96/15248, WO 96/19581, WO 96/27674,
WO 97/1 1 188, WO 97/26362, WO 97/32985, WO 97/42328, WO 97/44472, WO 97/1 1 188, WO 97/26362, WO 97/32985, WO 97/42328, WO 97/44472,
WO 97/45545, WO 98/27212, WO 98/40503, WO 99/58688, WO 99/58690, WO 97/45545, WO 98/27212, WO 98/40503, WO 99/58688, WO 99/58690,
WO 99/58654, WO 2000/008184, WO 2000/008185, WO 2000/28052, WO 99/58654, WO 2000/008184, WO 2000/008185, WO 2000/28052,
WO 2000/77229, WO 2001/12782, WO 2001 /12826, WO 2002/101059, WO 2000/77229, WO 2001/12782, WO 2001/12826, WO 2002/101059,
WO 2003/071860, WO 2004/056999, WO 2005/030942, WO 2005/030941 , WO 2003/071860, WO 2004/056999, WO 2005/030942, WO 2005/030941,
WO 2005/095632, WO 2005/095617, WO 2005/095619, WO 2005/095618, WO 2005/095632, WO 2005/095617, WO 2005/095619, WO 2005/095618,
WO 2005/123927, WO 2006/018319, WO 2006/103107, WO 2006/108702, WO 2005/123927, WO 2006/018319, WO 2006/103107, WO 2006/108702,
WO 2007/009823, WO 2000/22140, WO 2006/063862, WO 2006/072603, WO 2007/009823, WO 2000/22140, WO 2006/063862, WO 2006/072603,
WO 2002/034923, EP 06090134.5, EP 06090228.5, EP 06090227.7, EP 07090007.1 , EP 07090009.7, WO 2001/14569, WO 2002/79410, WO 2003/33540, EP 06090227.7, EP 07090007.1, EP 07090009.7, WO 2001/34923
WO 2004/078983, WO 2001/19975, WO 95/26407, WO 96/34968, WO 98/20145,
WO 99/12950, WO 99/66050, WO 99/53072, US 6,734,341 , WO 2000/1 1 192, WO 98/22604, WO 98/32326, WO 2001/98509, WO 2001/98509, WO 2005/002359, US 5,824,790, US 6.013,861 , WO 94/004693, WO 94/009144, WO 94/1 1520, WO 2004/078983, WO 2001/19975, WO 95/26407, WO 96/34968, WO 98/20145, WO 99/12950, WO 99/66050, WO 99/53072, US 6,734,341, WO 2000/1 1 192, WO 98/22604, WO 98/32326, WO 2001/98509, WO 2001/98509, WO 2005/002359, US 5,824,790, US 6,013,861, WO 94/004693, WO 94/009144, WO 94/1 1520,
WO 95/35026 bzw. WO 97/20936 beschrieben. WO 95/35026 and WO 97/20936, respectively.
2) Transgene Pflanzen, die Nichtstärkekohlenhydratpolymere synthetisieren, oder Nichtstärkekohlenhydratpolymere, deren Eigenschaften im Vergleich zu 2) Transgenic plants that synthesize non-starch carbohydrate polymers, or non-starch carbohydrate polymers whose properties are compared to
Wildtyppflanzen ohne genetische Modifikation verändert sind. Beispiele sind Pflanzen, die Polyfructose, insbesondere des Inulin- und Levantyps, produzieren, wie dies in EP 0663956, WO 96/001904, Wo 96/021023, WO 98/039460 und WO 99/024593 beschrieben ist, Pflanzen, die alpha-1 ,4-Glucane produzieren, wie dies in WO Wildtype plants are modified without genetic modification. Examples are plants which produce polyfructose, in particular of the inulin and levan type, as described in EP 0663956, WO 96/001904, Wo 96/021023, WO 98/039460 and WO 99/024593, plants which are alpha-1 To produce 4-glucans, as in WO
95/031553, US 2002/031826, US 6,284.479, US 5,712,107, WO 97/047806, WO 97/047807, WO 97/047808 und WO 2000/14249 beschrieben ist, Pflanzen, die alpha- 1 ,6-verzweigte alpha-1 .4-Glucane produzieren, wie dies in WO 2000/73422 95/031553, US 2002/031826, US 6,284,479, US 5,712,107, WO 97/047806, WO 97/047807, WO 97/047808 and WO 2000/14249, plants which are alpha-1, 6-branched alpha-1 4-glucans, as described in WO 2000/73422
beschrieben ist, und Pflanzen, die Alternan produzieren, wie dies in WO 2000/047727, EP 06077301 .7, US 5,908,975 und EP 0728213 beschrieben ist. and plants which produce alternan, as described in WO 2000/047727, EP 06077301.7, US 5,908,975 and EP 0728213.
3) Transgene Pflanzen, die Hyaluronan produzieren, wie dies zum Beispiel in WO 06/032538, WO 2007/039314, WO 2007/039315, WO 2007/039316, JP 2006/304779 und WO 2005/012529 beschrieben ist. 3) Transgenic plants which produce hyaluronan, as described, for example, in WO 06/032538, WO 2007/039314, WO 2007/039315, WO 2007/039316, JP 2006/304779 and WO 2005/012529.
Pflanzen oder Pflanzensorten (die nach Methoden der pflanzlichen Biotechnologie, wie der Gentechnik, erhalten wurden), die ebenfalls mit den erfindungsgemäßen Plants or plant varieties (obtained by plant biotechnology methods, such as genetic engineering), which are also with the inventive
Verbindungen der allgemeinen Formel (I) behandelt werden können, sind Pflanzen wie Baumwollpflanzen mit veränderten Fasereigenschaften. Solche Pflanzen können durch genetische Transformation oder durch Selektion von Pflanzen, die eine Mutation enthalten, die solche veränderten Fasereigenschaften verleiht, erhalten werden; dazu zählen: a) Pflanzen wie Baumwollpflanzen, die eine veränderte Form von Compounds of general formula (I) can be treated are plants such as cotton plants with altered fiber properties. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such altered fiber properties; These include: a) plants, such as cotton plants, which have an altered form of
Cellulosesynthasegenen enthalten, wie dies in WO 98/000549 beschrieben ist, b) Pflanzen wie Baumwollpflanzen, die eine veränderte Form von rsw2- oder rsw3- homologen Nukleinsäuren enthalten, wie dies in WO 2004/053219 beschrieben ist;
c) Pflanzen wie Baumwollpflanzen mit einer erhöhten Expression der Contain cellulose synthase genes, as described in WO 98/000549, b) plants such as cotton plants containing an altered form of rsw2 or rsw3 homologous nucleic acids, as described in WO 2004/053219; c) plants such as cotton plants with an increased expression of the
Saccharosephosphatsynthase, wie dies in WO 2001 /017333 beschrieben ist; d) Pflanzen wie Baumwollpflanzen mit einer erhöhten Expression der Sucrose phosphate synthase as described in WO 2001/017333; d) plants such as cotton plants with an increased expression of
Saccharosesynthase, wie dies in WO 02/45485 beschrieben ist; e) Pflanzen wie Baumwollpflanzen bei denen der Zeitpunkt der Durchlaßsteuerung der Plasmodesmen an der Basis der Faserzelle verändert ist, z. B. durch Sucrose synthase as described in WO 02/45485; e) plants such as cotton plants in which the timing of the passage control of the Plasmodesmen is changed at the base of the fiber cell, z. B. by
Herunterregulieren der faserselektiven ß-1 ,3-Glucanase, wie dies in WO 2005/017157 beschrieben ist; f) Pflanzen wie Baumwollpflanzen mit Fasern mit veränderter Reaktivität, z. B. durch Expression des N-Acetylglucosamintransferasegens, darunter auch nodC, und von Chitinsynthasegenen, wie dies in WO 2006/136351 beschrieben ist. Down-regulating the fiber-selective β-1,3-glucanase as described in WO 2005/017157; f) plants such as cotton plants with modified reactivity fibers, e.g. By expression of the N-acetylglucosamine transferase gene, including nodC, and chitin synthase genes, as described in WO 2006/136351.
Pflanzen oder Pflanzensorten (die nach Methoden der pflanzlichen Biotechnologie, wie der Gentechnik, erhalten wurden), die ebenfalls mit den erfindungsgemäßen Plants or plant varieties (obtained by plant biotechnology methods, such as genetic engineering), which are also with the inventive
Verbindungen der allgemeinen Formel (I) behandelt werden können, sind Pflanzen wie Raps oder verwandte Brassica-Pflanzen mit veränderten Eigenschaften der ölzusammensetzung. Solche Pflanzen können durch genetische Transformation oder durch Selektion von Pflanzen, die eine Mutation enthalten, die solche veränderten öleigenschaften verleiht, erhalten werden; dazu zählen: a) Pflanzen wie Rapspflanzen, die Öl mit einem hohen ölsäuregehalt produzieren, wie dies zum Beispiel in US 5,969,169, US 5,840,946 oder US 6.323.392 oder US 6,063, 947 beschrieben ist; b) Pflanzen wie Rapspflanzen, die Öl mit einem niedrigen Linolensäuregehalt produzieren, wie dies in US 6,270828, US 6.169,190 oder US 5,965,755 beschrieben ist.
c) Pflanzen wie Rapspflanzen, die Öl mit einem niedrigen gesättigten Compounds of general formula (I) can be treated are plants such as rapeseed or related Brassica plants with altered properties of the oil composition. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such altered oil properties; These include: a) plants such as rape plants that produce high oleic acid oil, as described, for example, in US 5,969,169, US 5,840,946 or US 6,323,392 or US 6,063,947; b) plants such as rape plants which produce low linolenic acid oil, as described in US 6,270,828, US 6,169,190 or US 5,965,755. c) plants such as rape plants, the oil with a low saturated
Fettsäuregehalt produzieren, wie dies z. B. in US 5,434,283 beschrieben ist. Produce fatty acid content, as z. As described in US 5,434,283.
Besonders nützliche transgene Pflanzen, die mit den erfindungsgemäßen Particularly useful transgenic plants with the inventive
Verbindungen der allgemeinen Formel (I) behandelt werden können, sind Pflanzen, die Transformations-Events, oder eine Kombination von Transformations-Events, enthalten und die zum Beispiel in den Dateien von verschiedenen nationalen oder regionalen Behörden angeführt sind. Besonders nützliche transgene Pflanzen, die mit den erfindungsgemäßen Compounds of general formula (I) may be treated as plants containing transformation events, or a combination of transformation events, for example as listed in the files of various national or regional authorities. Particularly useful transgenic plants with the inventive
Verbindungen der allgemeinen Formel (I) behandelt werden können, sind beispielhaft Pflanzen mit einem oder mehreren Genen, die für ein oder mehrere Toxine kodieren, sind die transgenen Pflanzen, die unter den folgenden Handelsbezeichnungen angeboten werden: YIELD GARD® (zum Beispiel Mais, Baumwolle, Sojabohnen), KnockOut® (zum Beispiel Mais), BiteGard® (zum Beispiel Mais), BT-Xtra® (zum Beispiel Mais), StarLink® (zum Beispiel Mais), Bollgard® (Baumwolle), Nucotn® (Baumwolle), Nucotn 33B® (Baumwolle), NatureGard® (zum Beispiel Mais), Exemplary plants having one or more genes encoding one or more toxins are the transgenic plants available under the following tradenames: YIELD GARD® (for example, corn, cotton , Soybeans), KnockOut® (for example corn), BiteGard® (for example maize), BT-Xtra® (for example maize), StarLink® (for example corn), Bollgard® (cotton), Nucotn® (cotton), Nucotn 33B® (cotton), NatureGard® (for example corn),
Protecta® und NewLeaf® (Kartoffel). Herbizidtolerante Pflanzen, die zu erwähnen sind, sind zum Beispiel Maissorten, Baumwollsorten und Sojabohnensorten, die unter den folgenden Handelsbezeichnungen angeboten werden: Roundup Ready® Protecta® and NewLeaf® (potato). Herbicide-tolerant crops to be mentioned include, for example, corn, cotton and soybean varieties sold under the following tradenames: Roundup Ready®
(Glyphosatetoleranz, zum Beispiel Mais, Baumwolle, Sojabohne), Liberty Link® (Phosphinotricintoleranz, zum Beispiel Raps), IMI® (Imidazolinontoleranz) und SCS® (Sylfonylharnstofftoleranz), zum Beispiel Mais. Zu den herbizidresistenten Pflanzen (traditionell auf Herbizidtoleranz gezüchtete Pflanzen), die zu erwähnen sind, zählen die unter der Bezeichnung Clearfield® angebotenen Sorten (zum Beispiel Mais). (Glyphosate tolerance, for example corn, cotton, soybean), Liberty Link® (phosphinotricin tolerance, for example rapeseed), IMI® (imidazolinone tolerance) and SCS® (sylphonylurea tolerance), for example maize. Herbicide-resistant plants (plants traditionally grown for herbicide tolerance) to be mentioned include the varieties sold under the name Clearfield® (for example corn).
Die erfindungsgemäß zu verwendenden Verbindungen der Formel (I) können in übliche Formulierungen überführt werden, wie Lösungen, Emulsionen, Spritzpulver, wasser- und ölbasierte Suspensionen, Pulver, Stäubemittel, Pasten, lösliche Pulver, lösliche Granulate, Streugranulate, Suspensions-Emulsions-Konzentrate, Wirkstoff- imprägnierte Naturstoffe, Wirkstoff-imprägnierte synthetische Stoffe, Düngemittel sowie Feinstverkapselungen in polymeren Stoffen. Im Rahmen der vorliegenden
Erfindung ist es insbesondere bevorzugt, wenn die Verbindungen der allgemeinen Formel (I) in der Form einer Sprühformulieruing verwendet werden. The compounds of the formula (I) to be used according to the invention can be converted into customary formulations, such as solutions, emulsions, wettable powders, water- and oil-based suspensions, powders, dusts, pastes, soluble powders, soluble granules, scattering granules, suspension-emulsion concentrates, Active substance-impregnated natural substances, active substance-impregnated synthetic substances, fertilizers and microencapsulation in polymeric substances. In the context of the present It is particularly preferred for the invention to use the compounds of general formula (I) in the form of a spray formulation.
Die vorliegende Erfindung betrifft daher darüber hinaus auch eine Sprühformulierung zur Steigerung der Widerstandsfähigkeit von Pflanzen gegenüber abiotischem Stress. Im Folgenden wird eine Sprühformulierung näher beschrieben: The present invention therefore further relates to a spray formulation for increasing the resistance of plants to abiotic stress. In the following, a spray formulation is described in more detail:
Die Formulierungen zur Sprühapplikation werden in bekannter Weise hergestellt, z.B. durch Vermischen der erfindungsgemäß zu verwendenden Verbindungen der aligmeinen Formel (I) mit Streckmitteln, also flüssigen Lösungsmitteln und/oder festen Trägerstoffen, gegebenenfalls unter Verwendung von oberflächenaktiven Mitteln, also Emulgiermitteln und/oder Dispergiermitteln und/oder schaumerzeugenden Mitteln. Weitere übliche Zusatzstoffe, wie zum Beispiel übliche Streckmittel sowie Lösungsoder Verdünnungsmittel, Farbstoffe, Netzmittel, Dispergiermittel, Emulgatoren, Entschäumer, Konservierungsmittel, sekundäre Verdickungsmittel, Kleber, The formulations for spray application are prepared in a known manner, e.g. by mixing the compounds of the formula (I) to be used according to the invention with extenders, ie liquid solvents and / or solid carriers, if appropriate using surface-active agents, ie emulsifiers and / or dispersants and / or foam-forming agents. Other conventional additives, such as conventional extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives,
Gibberelline und auch Wasser, können gegebenenfalls auch verwendet werden. Die Herstellung der Formulierungen erfolgt entweder in geeigneten Anlagen oder auch vor oder während der Anwendung. Als Hilfsstoffe können solche Stoffe Verwendung finden, die geeignet sind, dem Mittel selbst oder und/oder davon abgeleitete Zubereitungen (z.B. Spritzbrühen) besondere Eigenschaften zu verleihen, wie bestimmte technische Eigenschaften und/oder auch besondere biologische Eigenschaften. Als typische Hilfsmittel kommen in Frage: Gibberellins and also water may also be used if necessary. The preparation of the formulations is carried out either in suitable systems or before or during use. Excipients which can be used are those which are suitable for imparting special properties to the composition itself or to preparations derived therefrom (for example spray mixtures), such as certain technical properties and / or special biological properties. As typical aids are:
Streckmittel, Lösemittel und Trägerstoffe. Extenders, solvents and carriers.
Als Streckmittel eignen sich z.B. Wasser, polare und unpolare organische chemische Flüssigkeiten z.B. aus den Klassen der aromatischen und nicht-aromatischen As extender, e.g. Water, polar and non-polar organic chemical liquids e.g. from the classes of aromatic and non-aromatic
Kohlenwasserstoffe (wie Paraffine, Alkylbenzole, Alkylnaphthaline, Chlorbenzole), der Alkohole und Polyole (die ggf. auch substituiert, verethert und/oder verestert sein können), der Ketone (wie Aceton, Cyclohexanon), Ester (auch Fette und öle) und (Poly-)Ether, der einfachen und substituierten Amine, Amide, Lactame (wie N- Alkylpyrrolidone) und Lactone, der Sulfone und Sulfoxide (wie Dimethylsysulfoxid).
Im Falle der Benutzung von Wasser als Streckmittel können z.B. auch organische Lösemittel als Hilfsiösungsmittel verwendet werden. Als flüssige Lösemittel kommen im wesentlichen in Frage: Aromaten, wie Xylol, Toluol, oder Alkylnaphthaline, chlorierte Aromaten und chlorierte aliphatische Kohlenwasserstoffe, wie Chlorbenzole, Chlorethylene oder Methylenchlorid, aliphatische Kohlenwasserstoffe, wie Cyclohexan oder Paraffine, z.B. Erdölfraktionen, mineralische und pflanzliche Öle, Alkohole, wie Butanol oder Glykol sowie deren Ether und Ester, Ketone wie Aceton, Methylethyl- keton, Methylisobutylketon oder Cyclohexanon, stark polare Lösungsmittel, wie Hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), alcohols and polyols (which may also be substituted, etherified and / or esterified), ketones (such as acetone, cyclohexanone), esters (including fats and oils) and ( Poly) ethers, simple and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, sulfones and sulfoxides (such as dimethyl sulfoxide). In the case of using water as extender, for example, organic solvents can also be used as auxiliary solvents. Suitable liquid solvents are essentially: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as
Dimethylsulfoxid, sowie Wasser. Dimethyl sulfoxide, as well as water.
Es können Farbstoffe wie anorganische Pigmente, z.B. Eisenoxid, Titanoxid, Ferro- cyanblau und organische Farbstoffe, wie Alizarin-, Azo- und Metallphthalocyanin- farb Stoffe und Spurennährstoffe wie Salze von Eisen, Mangan, Bor, Kupfer, Kobalt, Molybdän und Zink verwendet werden. Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
Als Netzmittel, die in den erfindungsgemäß verwendbaren Formulierungen enthalten sein können, kommen alle zur Formulierung von agrochemischen Wirkstoffen üblichen, die Benetzung fördernden Stoffe in Frage. Vorzugsweise verwendbar sind Alkylnaphthalin-Sulfonate, wie Diisopropyl- oder Diisobutylnaphthalin-Sulfonate. Suitable wetting agents which may be present in the formulations which can be used according to the invention are all wetting-promoting substances customary for the formulation of agrochemical active compounds. Preferably usable are alkylnaphthalene sulfonates such as diisopropyl or diisobutylnaphthalene sulfonates.
Als Dispergiermittel und/oder Emulgatoren, die in den erfindungsgemäß verwendbaren Formulierungen enthalten sein können, kommen alle zur Formulierung von agrochemischen Wirkstoffen üblichen nichtionischen, anionischen und kationischen Dispergiermittel in Betracht. Vorzugsweise verwendbar sind nichtionische oder anionische Dispergiermittel oder Gemische von nichtionischen oder anionischen Dispergiermitteln. Als geeignete nichtionische Dispergiermittel sind insbesondere Ethylenoxid- Propylenoxid-Blockpolymere, Alkylphenolpolyglykolether sowie Tristryrylphenol- polyglykolether und deren phosphatierte oder sulfatierte Derivate zu nennen. Geeignete anionische Dispergiermittel sind insbesondere Ligninsulfonate, Poly- acrylsäuresalze und Arylsulfonat-Formaldehydkondensate. Suitable dispersants and / or emulsifiers which may be present in the formulations which can be used according to the invention are all nonionic, anionic and cationic dispersants customary for the formulation of agrochemical active compounds. Preferably usable are nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants. Particularly suitable nonionic dispersants are ethylene oxide-propylene oxide block polymers, alkylphenol polyglycol ethers and tristryrylphenol polyglycol ethers and their phosphated or sulfated derivatives. Suitable anionic dispersants are in particular lignosulfonates, polyacrylic acid salts and arylsulfonate-formaldehyde condensates.
Als Entschäumer können in den erfindungsgemäß verwendbaren Formulierungen alle zur Formulierung von agrochemischen Wirkstoffen üblichen schaumhemmenden
Stoffe enthalten sein. Vorzugsweise verwendbar sind Silikonentschäumer und Magne- siumstearat. Defoamers which can be used in the formulations which can be used according to the invention are all foam-inhibiting substances customary for the formulation of agrochemical active compounds Be contained substances. Preference is given to using silicone defoamers and magnesium stearate.
Als Konservierungsmittel können in den erfindungsgemäß verwendbaren As preservatives can be used in the invention
Formulierungen alle für derartige Zwecke in agrochemischen Mitteln einsetzbaren Stoffe vorhanden sein. Beispielhaft genannt seien Dichlorophen und Benzylalkohol- hemiformal. Formulations all substances that can be used for such purposes in agrochemical agents be present. Examples include dichlorophen and benzyl alcohol hemiformal.
Als sekundäre Verdickungsmittel, die in den erfindungsgemäß verwendbaren Formu- lierungen enthalten sein können, kommen alle für derartige Zwecke in agrochemischen Mitteln einsetzbaren Stoffe in Frage. Vorzugsweise in Betracht kommen Cellulose- derivate, Acrylsäurederivate, Xanthan, modifizierte Tone und hochdisperse Kieselsäure. Als Kleber, die in den erfindungsgemäß verwendbaren Formulierungen enthalten sein können, kommen alle üblichen in Beizmitteln einsetzbaren Bindemittel in Frage. Suitable secondary thickeners which may be present in the formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Preferably suitable are cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and finely divided silica. Suitable adhesives which may be present in the formulations which can be used according to the invention are all customary binders which can be used in pickling agents.
Vorzugsweise genannt seien Polyvinylpyrrolidon, Polyvinylacetat, Polyvinylalkohol und Tylose. Als Gibberelline, die in den erfindungsgemäß verwendbaren Formulierungen enthalten sein können, kommen vorzugsweise die Gibberelline A1 , A3 (= Preferably mentioned are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and Tylose. As gibberellins which may be present in the formulations which can be used according to the invention, the gibberellins A1, A3 (=
Gibberellinsäure), A4 und A7 infrage, besonders bevorzugt verwendet man die Gibberellinic acid), A4 and A7 in question, particularly preferably using the
Gibberellinsäure. Die Gibberelline sind bekannt (vgl. R. Wegler„Chemie der Gibberellic acid. The gibberellins are known (see R. Wegler "Chemie der
Pflanzenschutz- und Schädlingsbekämpfungsmittel", Bd. 2, Springer Verlag, 1970, S. 401 -412). Weitere Additive können Duftstoffe, mineralische oder vegetabilische gegebenenfalls modifizierte öle, Wachse und Nährstoffe (auch Spurennährstoffe), wie Salze von Eisen, Mangan, Bor, Kupfer, Kobalt, Molybdän und Zink sein. Weiterhin enthalten sein können Stabilisatoren wie Kältestabilisatoren, Oxidationsschutzmittel, Lichtschutzmittel oder andere die chemische und / oder physikalische Stabilität verbessernde Mittel. 2, Springer Verlag, 1970, pp. 401-412) Further additives may be fragrances, mineral or vegetable optionally modified oils, waxes and nutrients (also micronutrients), such as salts of iron, manganese, boron , Copper, cobalt, molybdenum and zinc, stabilizers such as low-temperature stabilizers, antioxidants, light stabilizers or other chemical and / or physical stability-improving agents.
Die Formulierungen enthalten im allgemeinen zwischen 0.01 und 98 Gew.-%, vorzugsweise zwischen 0,5 und 90 %, der Verbindung der allgemeinen Formel (I).
Die erfindungsgemäßen Verbindungen der allgemeinen Formel (I) können in handelsüblichen Formulierungen sowie in den aus diesen Formulierungen bereiteten Anwendungsformen in Mischung mit anderen Wirkstoffen wie Insektiziden, The formulations generally contain between 0.01 and 98% by weight, preferably between 0.5 and 90%, of the compound of general formula (I). The compounds of the general formula (I) according to the invention can be prepared in commercial formulations and in the formulations prepared from these formulations in admixture with other active substances such as insecticides,
Lockstoffen, Sterilantien, Bakteriziden, Akariziden, Nematiziden, Fungiziden, wachstumsregulierenden Stoffen, Herbiziden, Safenern, Düngemitteln oder Attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators, herbicides, safeners, fertilizers or
Semiochemicals vorliegen. Semiochemicals are present.
Ferner lässt sich die beschriebene positive Wirkung der Verbindungen der Formel (I) auf die pflanzeneigenen Abwehrkräfte durch eine zusätzliche Behandlung mit insektziden, fungiziden oder bakteriziden Wirkstoffen unterstützen. Furthermore, the described positive effect of the compounds of the formula (I) on the plant's own defenses can be assisted by additional treatment with insecticidal, fungicidal or bactericidal active substances.
Bevorzugte Zeitpunkte für die Applikation der erfindungsgemäß zu verwendenden Verbindungen der allgemeinen Formel (I) oder deren Salze zur Steigerung der Resistenz gegenüber abiotischem Stress sind Boden-, Stamm- und/oder Preferred times for the application of the compounds of the general formula (I) to be used according to the invention or their salts for increasing the resistance to abiotic stress are soil, parent and / or
Blattbehandlungen mit den zugelassenen Aufwandmengen. Leaf treatments with the approved application rates.
Die erfindungsgemäß zu verwendenden Wirkstoffe der allgemeinen Formel (I) oder deren Salze können im Allgemeinen darüber hinaus in ihren handelsüblichen The active compounds of the general formula (I) or salts thereof to be used according to the invention can generally also be used in their commercial form
Formulierungen sowie in den aus diesen Formulierungen bereiteten Formulations and in those prepared from these formulations
Anwendungsformen in Mischungen mit anderen Wirkstoffen, wie Insektiziden, Lockstoffen, Sterilantien, Akariziden, Nematiziden, Fungiziden, Bakteriziden, wachstumsregulierenden Stoffen, die Pflanzenreife beeinflussenden Stoffen, Safenern oder Herbiziden vorliegen. Besonders günstige Mischpartner sind beispielsweise die nachfolgend gruppenweise genannten Wirkstoffe der verschiedenen Klassen, ohne dass durch deren Reihenfolge eine Präferenz gesetzt wird: Use forms in mixtures with other active ingredients, such as insecticides, attractants, sterilants, acaricides, nematicides, fungicides, bactericides, growth-regulating substances, the plant ripeness affecting substances, safeners or herbicides are present. Particularly favorable mixing partners are, for example, the active substances of the various classes which are mentioned below in groups, without preference being given to their order:
Fungizide: F1 ) Inhibitoren der Nucleinsäure Synthese, z. B. Benalaxyl, Benalaxyl-M, Bupirimat, Chiralaxyl, Clozylacon, Dimethirimol, Ethirimol, Furalaxyl, Hymexazol, Metalaxyl, Metalaxyl-M, Ofurace, Oxadixyl, Oxolinsäure;
F2) Inhibitoren der Mitose und Zellteilung, z. B. Benomyl, Carbendazim, Diethofencarb, Fuberidazole, Fluopicolid, Pencycuron, Thiabendazol, Thiophanat-methyl, Zoxamid und Chlor-7-(4-methylpiperidin-1 -yl)-6-(2.4,6- Trifluorphenyl [1 ,2.4]triazolo[1 ,5- a]pyrimidin; Fungicides: F1) inhibitors of nucleic acid synthesis, e.g. Benalaxyl, benalaxyl-M, bupirimate, chiralaxyl, clozylacon, dimethirimol, ethirimol, furalaxyl, hymexazole, metalaxyl, metalaxyl-M, ofurace, oxadixyl, oxolinic acid; F2) inhibitors of mitosis and cell division, e.g. Benomyl, carbendazim, diethofencarb, fuberidazole, fluopicolide, pencycuron, thiabendazole, thiophanate-methyl, zoxamide and chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl [1,2,4] triazolo [1, 5-a] pyrimidine;
F3) Inhibitoren der Atmungskette Komplex I / II, z. B. Diflumetorim, Bixafen, Boscalid, Carboxin, Diflumethorim Fenfuram, Fluopyram, Flutolanil, Furametpyr, Mepronil, Oxycarboxin, Penflufen, Penthiopyrad, Thifiuzamid, N-[2-(1 ,3-Dimethylbutyl)phenyl]-5- fluor-1 ,3-dimethyl-1 H-pyrazol-4-carboxamid, Isopyrazam, Sedaxan, 3-(Difluormethyl)- 1 -methyl-N-(3,,4,,5'-trifluorbiphenyl-2-yl)-1 H-pyrazol-4-carboxamid, 3-(Difluormethyl)-1- methyl-N-[2-(1 ,1 ,2.2-tetrafluorethoxy)phenyl]-1 H-pyrazol-4-carboxamid, 3- (Difluormethyl)-N-[4-fluoro-2-(1 ,1 ,2,3.3,3-hexafluorpropoxy)phenyl]-1 -methyl-1 H- pyrazol-4-carboxamid, N-[1 -(2,4-Dichlorphenyl)-1 -methoxypropan-2-yl]-3- (difluormethyl)-l -methyl-1 H-pyrazol-4-carboxamid und entsprechende Salze; F3) inhibitors of the respiratory chain complex I / II, z. Diflumetorim, bixafen, boscalid, carboxin, diflumethorim fenfuram, fluopyram, flutolanil, furametpyr, mepronil, oxycarboxin, penflufen, penthiopyrad, thifiuzamide, N- [2- (1, 3-dimethylbutyl) phenyl] -5-fluoro-1, 3-dimethyl-1 H-pyrazole-4-carboxamide, isopyrazam, Sedaxane, 3- (difluoromethyl) - 1 -methyl-N- (3,, 4,, 5'-trifluorobiphenyl-2-yl) -1 H-pyrazol 4-carboxamide, 3- (difluoromethyl) -1-methyl-N- [2- (1, 1, 2.2-tetrafluoroethoxy) phenyl] -1H-pyrazole-4-carboxamide, 3- (difluoromethyl) -N- [ 4-fluoro-2- (1,1,3,3,3-hexafluoropropoxy) phenyl] -1-methyl-1H-pyrazole-4-carboxamide, N- [1- (2,4-dichlorophenyl) -1 - methoxypropan-2-yl] -3- (difluoromethyl) -1-methyl-1H-pyrazole-4-carboxamide and corresponding salts;
F4) Inhibitoren der Atmungskette Komplex III, z. B.Amisulbrom, Azoxystrobin, F4) inhibitors of the respiratory chain complex III, z. B. amisulbrom, azoxystrobin,
Cyazofamid, Dimoxystrobin, Enestrobin, Famoxadon, Fenamidon, Fluoxastrobin, Kresoximmethyl, Metominostrobin, Orysastrobin, Pyraclostrobin, Pyribencarb, Cyazofamide, dimoxystrobin, enestrobin, famoxadone, fenamidone, fluoxastrobin, kresoximethyl, metominostrobin, orysastrobin, pyraclostrobin, pyribencarb,
Picoxystrobin, Trifloxystrobin, (2E)-2-(2-{[6-(3-Chlor-2-methylphenoxy)-5- fluorpyrimidin-4-yl]oxy}phenyl)-2-(methoxyimino)-N-methylethanamid, (2E)-2- (Ethoxyimino)-N-methyl-2-(2-{[({(1 E)-1 -[3-(trifluoromethyl)- phenyl]ethyliden}amino)oxy]methyl}phenyl)ethanamid und entsprechende Salze, (2E)- 2-(Methoxyimino)-N-methyl-2-{2-[(E)-({1 -[3-(trifluormethyl)phenyl]ethoxy}- imino)methyl]phenyl}ethanamid, (2E)-2-{2-[({[(1 E)-1 -(3-{[(E)-1 -Fluor-2-phenylethenyl]- oxy}phenyl)ethyliden]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylethanamid, (2E)-2-{2-[({[(2E,3E)-4-(2,6-Dichlorophenyl)but-3-en-2- yliden]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylethanamid, 2-Chlor-N- (1 ,1 ,3-trimethyl-2,3-dihydro-1 H-inden-4-yl)pyridin-3-carboxamid, 5-Methoxy-2-methyl- 4-(2-{[({(1 E)-1 -[3-(trifluormethyl)phenyl]ethyliden}amino)oxy]methyl}phenyl)-2,4- dihydro-3H-1 ,2.4-triazol-3-on, 2-Methyl-{2-[({cyclopropyl[(4-methoxyphenyl)- imino]methyl}sulfanyl)methyl]phenyl}-3-methoxyacrylat, N-(3-Ethyl-3,5,5- trimethylcyclohexyl)-3-(formylamino)-2-hydroxybenzamid und entsprechende Salze; Picoxystrobin, trifloxystrobin, (2E) -2- (2 - {[6- (3-chloro-2-methylphenoxy) -5-fluoropyrimidin-4-yl] oxy} phenyl) -2- (methoxyimino) -N-methylethanamide, (2E) -2- (ethoxyimino) -N-methyl-2- (2 - {[({(1E) -1 - [3- (trifluoromethyl) phenyl] ethylidene} amino) oxy] methyl} phenyl) ethanamide and corresponding salts, (2E) -2- (methoxyimino) -N-methyl-2- {2 - [(E) - ({1- [3- (trifluoromethyl) phenyl] ethoxy} - imino) methyl] phenyl} ethanamide , (2E) -2- {2 - [({[(1 E) -1 - (3 - {[(E) -1-fluoro-2-phenylethenyl] oxy} phenyl) ethylidene] amino} oxy) methyl ] phenyl} -2- (methoxyimino) -N-methylethaneamide, (2E) -2- {2 - [({[(2E, 3E) -4- (2,6-dichlorophenyl) -but-3-en-2-] yliden] amino} oxy) methyl] phenyl} -2- (methoxyimino) -N-methylethaneamide, 2-chloro-N- (1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl ) pyridine-3-carboxamide, 5-methoxy-2-methyl-4- (2 - {[({(1 E) -1 - [3- (trifluoromethyl) phenyl] ethylidene} amino) oxy] methyl} phenyl) - 2,4-dihydro-3H-1, 2,4-triazol-3-one, 2-methyl {2 - [({cyclopropyl [(4-methoxyphenyl) imino] methyl} sulfanyl) methyl] phenyl} -3-methoxyacrylate , N- (3-ethyl-3,5,5 trimethylcyclohexyl) -3- (formylamino) -2-hydroxybenzamide and corresponding salts;
F5) Entkoppler, z. B. Dinocap, Fluazinam;
F6) Inhibitoren der ATP Produktion, z. B. Fentinacetat, Fentinchlorid, Fentinhydroxid, Silthiofam F7) Inhibitoren der Aminosäure- und Proteinbiosynthese, z.B. Andoprim, Blasticidin-S, Cyprodinil, Kasugamycin, Kasugamycinhydrochlorid Hydrat, Mepanipyrim, F5) decoupler, z. Dinocap, fluazinam; F6) inhibitors of ATP production, e.g. Fentin acetate, fentin chloride, fentin hydroxide, silthiofam F7) inhibitors of amino acid and protein biosynthesis, eg, andoprim, blasticidin-S, cyprodinil, kasugamycin, kasugamycin hydrochloride hydrate, mepanipyrim,
Pyrimethanil pyrimethanil
F8) Inhibitoren der Signal-Transduktion, z. B. Fenpiclonil, Fludioxonil, Quinoxyfen F8) inhibitors of signal transduction, e.g. Fenpiclonil, fludioxonil, quinoxyfen
F9) Inhibitoren der Fett- und Membran Synthese, z. B. Chlozolinat, Iprodion, F9) inhibitors of fat and membrane synthesis, e.g. B. chlozolinate, iprodione,
Procymidon, Vinclozolin, Ampropylfos, Kalium-Ampropylfos, Edifenphos, Iprobenfos (IBP), Isoprothiolan, Pyrazophos, Tolclofos-methyl, Biphenyl, lodocarb, Propamocarb, Propamocarb hydrochlorid Procymidone, Vinclozolin, Ampropylfos, Potassium-Ampropylfos, Edifenphos, Iprobenfos (IBP), Isoprothiolane, Pyrazophos, Tolclofos-methyl, Biphenyl, iodocarb, Propamocarb, Propamocarb hydrochloride
F10) Inhibitoren der Ergosterol Biosynthese, z. B. Fenhexamid, Azaconazol, Bitertanol, Bromuconazol, Diclobutrazol, Difenoconazol, Diniconazol, Diniconazol-M, Etaconazol, Fenbuconazol, Fluquinconazol, Flusilazol, Flutriafol, Furconazol, Furconazol-cis, Hexaconazol, Imibenconazol, Ipconazol, Metconazol, Myclobutanil, Paclobutrazol, Penconazol, Propiconazol, Prothioconazol, Simeconazol, Spiroxamin, Tebuconazol, Triadimefon, Triadimenol, Triticonazol, Uniconazol, Voriconazol, Imazalil, F10) inhibitors of ergosterol biosynthesis, eg. Fenhexamid, azaconazole, bitertanol, bromuconazole, diclobutrazole, difenoconazole, diniconazole, diniconazole-M, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, furconazole, furconazole-cis, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, paclobutrazole, penconazole, Propiconazole, Prothioconazole, Simeconazole, Spiroxamine, Tebuconazole, Triadimefon, Triadimenol, Triticonazole, Uniconazole, Voriconazole, Imazalil,
Imazalilsulfat, Oxpoconazol, Fenarimol, Flurprimidol, Nuarimol, Pyrifenox, Triforin, Pefurazoat, Prochloraz, Triflumizol, Viniconazol, Aldimorph, Dodemorph, Imazalil sulfate, oxpoconazole, fenarimol, flurprimidol, nuarimol, pyrifenox, triforin, pefurazoate, prochloraz, triflumizole, viniconazole, aldimorph, dodemorph,
Dodemorphacetat, Fenpropimorph, Tridemorph, Fenpropidin, Naftifin, Pyributicarb, Terbinafin, 1 -(4-Chlorophenyl)-2-(1 H-1 .2,4-triazol-1 -yl)cycloheptanol, Methyl-1 -(2.2- dimethyl-2.3-dihydro-1 H-inden-1 -yl)-1 H-imidazol-5-carboxylat, N'-{5-(Difiuormethyl)-2- methyl-4-[3-(trimethyl-silyl)propoxy]phenyl}-N-ethyl-N-methylimidoformamid, N-Ethyl- N-methyl-N'-{2-methyl-5-(trifluormethyl)-4-[3-Dodemorphoacetate, fenpropimorph, tridemorph, fenpropidine, naftifine, pyributicarb, terbinafine, 1- (4-chlorophenyl) -2- (1H-1, 2,4-triazol-1-yl) cycloheptanol, methyl-1 - (2.2-dimethyl -2,3-dihydro-1H-inden-1-yl) -1H-imidazole-5-carboxylate, N '- {5- (difluoromethyl) -2-methyl-4- [3- (trimethyl-silyl) -propoxy] phenyl} -N-ethyl-N-methylimidoformamide, N-ethyl-N-methyl-N '- {2-methyl-5- (trifluoromethyl) -4- [3-
(trimethylsilyl)propoxy]phenyl}imidoformamid und 0-{1 -[(4-Methoxy-phenoxy)methyl]- 2,2-dimethylpropyl}-1 H-imidazol-1 -carbothioat; (trimethylsilyl) propoxy] phenyl} imidoformamide and 0- {1 - [(4-methoxyphenoxy) methyl] -2,2-dimethylpropyl} -1H-imidazole-1-carbothioate;
F1 1 ) Inhibitoren der Zellwand Synthese, z. B. Benthiavalicarb, Bialaphos, F1 1) inhibitors of cell wall synthesis, e.g. Benthiavalicarb, Bialaphos,
Dimethomorph, Flumorph, Iprovalicarb, Polyoxins, Polyoxorim, Validamycin A
F12) Inhibitoren der Melanin Biosynthese, z. B. Capropamid, Diclocymet, Fenoxanil, Phtalid, Pyroquilon, Tricyclazol Dimethomorph, flumorph, iprovalicarb, polyoxins, polyoxorim, validamycin A F12) inhibitors of melanin biosynthesis, e.g. Capropamide, diclocymet, fenoxanil, phtalid, pyroquilon, tricyclazole
F13) Resistenzinduktion, z. B. Acibenzolar-S-methyl, Probenazol, Tiadinil F13) resistance induction, e.g. Acibenzolar-S-methyl, probenazole, tiadinil
F14) Multisite, z. B. Captafol, Captan, Chlorothalonil, Kupfersalze wie: Kupferhydroxid, Kupfernaphthenat, Kupferoxychlorid, Kupfersulfat, Kupferoxid, Oxin-Kupfer und Bordeaux Mischung, Dichlofluanid, Dithianon, Dodin, Dodin freie Base, Ferbam, Folpet, Fluorofolpet, Guazatin, Guazatinacetat, Iminoctadin, Iminoctadinalbesilat, Iminoctadintriacetat, Mankupfer, Mancozeb, Maneb, Metiram, Metiram Zink, Propineb, Schwefel und Schwefelpräparate enthaltend Calciumpolysulphid, Thiram, Tolylfluanid, Zineb, Ziram F14) Multisite, z. B. Captafol, captan, chlorothalonil, copper salts such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, oxine-copper and Bordeaux mixture, Dichlofluanid, Dithianon, Dodin, Dodin free base, Ferbam, Folpet, Fluorofolpet, Guazatin, Guazatinacetat, iminoctadine, Iminoctadinalesilate, iminoctadine triacetate, mancopper, mancozeb, maneb, metiram, metiram zinc, propineb, sulfur and sulfur preparations containing calcium polysulphide, thiram, tolylfluanid, zineb, ziram
F15) Unbekannter Mechanismus, z. B. Amibromdol, Benthiazol, Bethoxazin, F15) Unknown mechanism, e.g. Amibromdole, benthiazole, bethoxazine,
Capsimycin, Carvon, Chinomethionat, Chloropicrin, Cufraneb, Cyflufenamid, Capsimycin, carvone, quinomethionate, chloropicrin, cufraneb, cyflufenamid,
Cymoxanil, Dazomet, Debacarb, Diclomezine, Dichlorophen, Dicloran, Difenzoquat, Difenzoquat Methylsulphat, Diphenylamin, Ethaboxam, Ferimzon, flumetover, Cymoxanil, Dazomet, Debacarb, Diclomezine, Dichlorophene, Dicloran, Difenzoquat, Difenzoquat Methylsulphate, Diphenylamine, Ethaboxam, Ferimzone, Flumetover,
Flusulfamid, Fluopicolid, Fluoroimid, Fosatyl-Al, Hexachlorobenzol, 8-Hydroxy- chinolinsulfat, Iprodione, Irumamycin, Isotianil, Methasulphocarb, Metrafenon, Methyl Isothiocyanat, Mildiomycin, Natamycin, Nickel dimethyldithiocarbamat, Nitrothal- isopropyl, Octhilinon, Oxamocarb, Oxyfenthiin, Pentachlorophenol und Salze, 2- Phenylphenol und Salze, Piperalin, Propanosin -Natrium, Proquinazid, Pyrrolnitrin, Quintozen, Tecloftalam, Tecnazen, Triazoxid, Trichlamid, Zarilamid und 2,3.5,6- Tetrachlor-4-(methylsulfonyl)-pyridin, N-(4-Chlor-2-nitrophenyl)-N-ethyl-4-methyl- benzenesulfonamid, 2-Amino-4-methyl-N-phenyl-5-thiazolecarboxamid, 2-Chlor-N- (2,3-dihydro-1 .1 ,3-trimethyl-1 H-inden-4-yl)-3-pyridincarboxamid, 3-[5-(4-Chlorphenyl)- 2,3-dimethylisoxazolidin-3-yl]pyridin, cis-1 -(4-Chlorphenyl)-2-(1 H-1 ,2,4-triazoM -yl)- cycloheptanol, 2,4-Dihydro-5-methoxy-2-methyl-4-[[[[1 -[3-(trifluoromethyl)-phenyl]- ethyliden]-amino]-oxy]-methyl]-phenyl]-3H-1 ,2,3-triazol-3-on (185336-79-2), Methyl 1 - (2,3-dihydro-2,2-dimethyl-1 H-inden-1 -yl)-1 H-imidazole-5-carboxylat, 3,4.5-Trichlor-2,6- pyridindicarbonitril, Methyl 2-[[[cyclopropyl[(4-methoxyphenyl) Flusulfamide, fluopicolide, fluoroimide, fosatyl-Al, hexachlorobenzene, 8-hydroxyquinoline sulfate, iprodione, irumamycin, isotianil, methasulphocarb, metrafenone, methyl isothiocyanate, mildiomycin, natamycin, nickel dimethyldithiocarbamate, nitrothal isopropyl, octhilinone, oxamocarb, oxyfenthiine, pentachlorophenol and Salts, 2-phenylphenol and salts, piperaline, propanosine sodium, proquinazide, pyrroline nitrine, quintozene, tecloftalam, tecnazene, triazoxide, trichlamide, zarilamide and 2,3,5,6-tetrachloro-4- (methylsulfonyl) -pyridine, N- (4 -Chloro-2-nitrophenyl) -N-ethyl-4-methyl-benzenesulfonamide, 2-amino-4-methyl-N-phenyl-5-thiazolecarboxamide, 2-chloro-N- (2,3-dihydro-1 .1 , 3-trimethyl-1H-inden-4-yl) -3-pyridinecarboxamide, 3- [5- (4-chlorophenyl) -2,3-dimethylisoxazolidin-3-yl] pyridine, cis-1 - (4-chlorophenyl ) -2- (1H-1,2,4-triazolyl) -cycloheptanol, 2,4-dihydro-5-methoxy-2-methyl-4 - [[[[1 - [3- (trifluoromethyl) - phenyl] ethylidene] amino] oxy] methyl] phenyl] -3H-1,2,3-triazol-3-one (185336-79-2), methyl 1 - (2,3-dihydro-2,2-dimethyl-1H-inden-1-yl) -1H-imidazole-5-carboxylate, 3,4,5-trichloro-2,6-pyridinedicarbonitrile, methyl 2 - [[ [cyclopropyl [(4-methoxyphenyl)
imino]methyl]thio]methyl]-. alpha. -(methoxymethylen)- benzacetat, 4-Chlor-alpha- propinyloxy-N-[2-[3-methoxy-4-(2-propinyloxy)phenyl]ethyl]-benzacetamide, (2S)-N-[2- [4-[[3-(4-chlorophenyl)-2-propinyl]oxy]-3-methoxyphenyl]ethyl]-3-methyl-2-[(methyl-
sulfonyl)amino]-butanamid, 5-Chlor-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)- [1 ,2,4]triazolo[1 ,5-a]pyrimidin, 5-Chlor-6-(2.4,6-trifluorophenyl)-N-[(1 R)-1 ,2,2-trimethyl- propyl][1 ,2,4]triazolo[1 ,5-a]pyrimidin-7-amin, 5-Chlor-N-[(1 R)-1 ,2-dimethylpropyl]-6- (2,4,6-trifluorophenyl) [1 ,2,4]triazolo[1 ,5-a]pyrimidin-7-amine, N-[1 -(5-Brom-3-chloro- pyridin-2-yl)ethyl]-2,4-dichloronicotinamid, N-(5-Brom-3-chlorpyridin-2-yl)methyl-2,4- dichlornicotinamid, 2-Butoxy-6-iod-3-propyl-benzopyranon-4-on, N-{(Z)-[(cyclopropyl- methoxy) imino][6-(dif!uormethoxy)-2,3-difluorphenyl]methyl}-2-benzacetamid, N-(3- Ethyl-3,5.5-trimethyl-cyclohexyl)-3-formylamino-2-hydroxy-benzamid, 2-[[[[1 -[3(1 Fluor- 2-phenylethyl)oxy] phenyl] ethyliden]amino]oxy]methyl]-alpha-(methoxyimino)-N- methyl-alphaE-benzacetamid, N-{2-[3-Chlor-5-(trifluormethyl)pyridin-2-yl]ethyl}-2- (trifluoromethyl)benzamid, N-(3'.4'-dichior-5-fluorbiphenyl-2-yl)-3-(difluormethyl)-1 - methyl-1 H-pyrazol-4-carboxamid, N-(6- ethoxy-3-pyridinyl)-cyclopropan carboxamid, 1 -[(4-Methoxyphenoxy)methyl]-2.2-dimethylpropyl-1 H-imidazol-1 - carbonsäure, 0-[1 - [(4-Methoxyphenoxy)methyl]-2,2-dimethylpropyl]-1 H-imidazol- 1 - carbothioic acid, 2-(2- {[6-(3-Chlor-2-methylphenoxy)-5-fluorpyrimidin-4-yl]oxy}phenyl)-2-(methoxyimin methylacetamid imino] methyl] thio] methyl] -. alpha. - (methoxymethylene) - benzoacetate, 4-chloro-alpha-propynyloxy-N- [2- [3-methoxy-4- (2-propynyloxy) phenyl] ethyl] -benzacetamide, (2S) -N- [2- [4 - [[3- (4-chlorophenyl) -2-propynyl] oxy] -3-methoxyphenyl] ethyl] -3-methyl-2 - [(methyl- sulfonyl) amino] butanamide, 5-chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) - [1, 2,4] triazolo [1,5-a] pyrimidine, 5-chloro-6- (2,4,6-trifluorophenyl) -N - [(1 R) -1, 2,2-trimethyl-propyl] [1,2,4] triazolo [1,5-a] pyrimidine 7-amine, 5-chloro-N - [(1R) -1,2-dimethylpropyl] -6- (2,4,6-trifluorophenyl) [1,2,4] triazolo [1,5-a] pyrimidin-7-amine, N- [1- (5-bromo-3-chloropyridin-2-yl) ethyl] -2,4-dichloronicotinamide, N- (5-bromo-3-chloropyridin-2-yl) methyl-2,4-dichloronotinamide, 2-butoxy-6-iodo-3-propyl-benzopyranon-4-one, N - {(Z) - [(cyclopropylmethoxy) imino] [6- (diformormethoxy) - 2,3-difluorophenyl] methyl} -2-benzacetamide, N- (3-ethyl-3,5,5-trimethylcyclohexyl) -3-formylamino-2-hydroxybenzamide, 2 - [[[[1 - [3 ( 1 fluoro-2-phenylethyl) oxy] phenyl] ethylidene] amino] oxy] methyl] -alpha (methoxyimino) -N-methyl-alpha-E-benzoacetamide, N- {2- [3-chloro-5- (trifluoromethyl) pyridine -2-yl] ethyl} -2- (trifluoromethyl) benzamide, N- (3'.4'-dichloro-5-fluorobiphenyl-2-yl) -3- (difluoromethyl) -1-methyl-1H-pyrazole 4-carboxamide, N- (6- e thoxy-3-pyridinyl) -cyclopropane carboxamide, 1 - [(4-methoxyphenoxy) methyl] -2,2-dimethylpropyl-1H-imidazole-1-carboxylic acid, 0- [1 - [(4-methoxyphenoxy) methyl] -2, 2-dimethylpropyl] -1H-imidazole-1-carbothioic acid, 2- (2- {[6- (3-chloro-2-methylphenoxy) -5-fluoropyrimidin-4-yl] oxy} phenyl) -2- ( methoxyimine methylacetamide
Bakterizide: Bronopol, Dichlorophen, Nitrapyrin, Nickel-Dimethyldithiocarbamat, Kasugamycin,Bactericides: bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin,
Octhilinon, Furancarbonsäure, Oxytetracyclin, Probenazoi, Streptomycin, Tecioftalam, Kupfersulfat und andere Kupfer-Zubereitungen. Octhilinone, furancarboxylic acid, oxytetracycline, probenazoi, streptomycin, tecioftalam, copper sulfate and other copper preparations.
Insektizide / Akarizide / Nematizide: Insecticides / acaricides / nematicides:
11 ) Acetylcholinesterase (AChE) Inhibitoren, wie beispielsweise Carbamate, z.B. 11) Acetylcholinesterase (AChE) inhibitors such as carbamates, e.g.
Alanycarb, Aldicarb, Bendiocarb, Benfuracarb, Butocarboxim, Butoxycarboxim, Carb- aryl, Carbofuran, Carbosulfan, Ethiofencarb, Fenobucarb, Formetanate, Furathiocarb, Isoprocarb, ethiocarb, Methomyl, Metolcarb, Oxamyl, Pirimicarb, Propoxur, Thio- dicarb, Thiofanox, Triazamate, Trimethacarb, XMC und Xylylcarb; oder Alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxime, butoxycarboxim, carbarnyl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, ethiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamates, Trimethacarb, XMC and xylylcarb; or
Organophosphate, z.B. Acephate, Azamethiphos, Azinphos (-methyl, -ethyl), Organophosphates, e.g. Acephates, azamethiphos, azinphos (-methyl, -ethyl),
Cadusafos, Chlorethoxyfos, Chlorfenvinphos, Chlormephos, Chlorpyrifos (-methyl), Coumaphos, Cyanophos, Demeton-S-methyl, Diazinon, Dichlorvos/DDVP, Cadusafos, Chlorethoxyfos, Chlorfenvinphos, Chlormephos, Chlorpyrifos (-methyl), Coumaphos, Cyanophos, Demeton-S-methyl, Diazinone, Dichlorvos / DDVP,
Dicrotophos, Dimethoate, Dimethylvinphos, Disulfoton, EPN, Ethion, Ethoprophos,
Famphur, Fenamiphos, Fenitrothion, Fenthion, Fosthiazate, Heptenophos, Isofenphos, Isopropyl O(methoxyaminothio-phosphoryl) salicylat, Isoxathion, Malathion, Me- carbam, Methamidophos, Methidathion, Mevinphos, Monocrotophos, Naled, Dicrotophos, dimethoates, dimethylvinphos, disulfonone, EPN, ethion, ethoprophos, Famphur, Fenamiphos, Fenitrothion, Fenthion, Fosthiazate, Heptenophos, Isofenphos, Isopropyl O (methoxyaminothio-phosphoryl) salicylate, Isoxathione, Malathion, Me-carbam, Methamidophos, Methidathione, Mevinphos, Monocrotophos, Naled,
Omethoate, Oxydemeton-methyl, Parathion (-methyl), Phenthoate, Phorate, Omethoate, Oxydemeton-methyl, Parathion (-methyl), Phenthoate, Phorate,
Phosalone, Phosmet, Phosphamidon, Phoxim, Pirimiphos (-methyl), Profenofos, Pro- petamphos, Prothiofos, Pyraclofos, Pyridaphenthion, Quinalphos, Sulfotep, Phosalone, Phosmet, Phosphamidone, Phoxim, Pirimiphos (-methyl), Profenofos, Propetamphos, Prothiofos, Pyraclofos, Pyridaphenthion, Quinalphos, Sulfotep,
Tebupirimfos, Temephos, Terbufos, Tetrachlorvinphos, Thiometon, Triazophos, Triclorfon und Vamidothion. 12) GABA-gesteuerte Chlorid-Kanal-Antagonisten, wie beispielsweise Organochlorine, z.B. Chlordane und Endosulfan (alpha-); oder Fiprole (Phenylpyrazole), z.B. Ethiprole, Fipronil, Pyrafluprole und Pyriprole. Tebupirimfos, Temephos, Terbufos, Tetrachlorvinphos, Thiometone, Triazophos, Triclorfon and Vamidothion. 12) GABA-controlled chloride channel antagonists, such as organochlorines, e.g. Chlordane and endosulfan (alpha); or fiproles (phenylpyrazoles), e.g. Ethiprole, Fipronil, Pyrafluprole and Pyriprole.
13) Natrium-Kanal-Modulatoren / Spannungsabhängige Natrium-Kanal-Blocker, wie beispielsweise Pyrethroide, z.B. Acrinathrin, Allethrin (d-cis-trans, d-trans), Bifenthrin, Bioallethrin, Bioallethrin-S-cyclopentenyl, Bioresmethrin, Cycloprothrin, Cyfluthrin (beta-), Cyhalothrin (gamma-, lambda-), Cypermethrin (alpha-, beta-, theta-, zeta-), Cy- phenothrin [(1 R)-trans-lsomere], Deltamethrin, Dimefluthrin, Empenthrin [(EZ)-(1 R)- Isomere], Esfenvalerate, Etofenprox, Fenpropathrin, Fenvalerate, Flucythrinate, Flu- methrin, Fluvalinate (tau-), Halfenprox, Imiprothrin, Metofluthrin, Permethrin, Pheno- thrin [(1 R)-trans-lsomer], Prallethrin, Profluthrin, Pyrethrine (pyrethrum), Resmethrin, RU 15525, Silafluofen, Tefluthrin, Tetra methrin [(1 R)- Isomere], Tralomethrin, 13) Sodium channel modulators / voltage dependent sodium channel blockers such as pyrethroids, e.g. Acrinathrin, allethrin (d-cis-trans, d-trans), bifenthrin, bioallethrin, bioallethrin S-cyclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin (beta-), cyhalothrin (gamma, lambda), cypermethrin (alpha-, beta , theta, zeta), cychenothrin [(1R) trans isomers], deltamethrin, dimefluthrin, empenthrin [(EZ) (1R) isomers], esfenvalerates, etofenprox, fenpropathrin, fenvalerates, flucythrinates , Flumethrin, fluvalinate (tau-), halfenprox, imiprothrin, metofluthrin, permethrin, phenothrin [(1R) -trans-isomer], prallethrin, profuthrin, pyrethrin (pyrethrum), resmethrin, RU 15525, silafluofen, tefluthrin , Tetra methrin [(1R) - isomers], tralomethrin,
Transfluthrin und ZXI 8901 ; oder_DDT; oder Methoxychlor. 14) Nikotinerge Acetylcholin-Rezeptor-Agonisten, wie beispielsweise Neonikotinoide, z.B. Acetamiprid, Clothianidin, Dinotefuran, Imidacloprid, Nitenpyram, Thiacloprid, Thiamethoxam; oder Nikotin. Transfluthrin and ZXI 8901; oder_DDT; or methoxychlor. 14) nicotinergic acetylcholine receptor agonists such as neonicotinoids, e.g. Acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam; or nicotine.
15) Allosterische Acetylcholin-Rezeptor-Modulatoren (Agonisten), wie beispielsweise Spinosyne, z.B. Spinetoram und Spinosad. 15) Allosteric acetylcholine receptor modulators (agonists), such as spinosyns, e.g. Spinetoram and spinosad.
16) Chlorid-Kanal-Aktivatoren, wie beispielsweise Avermectine/Milbemycine, z.B. 16) chloride channel activators, such as avermectins / milbemycins, e.g.
Abamectin, Emamectin, Emamectin-benzoate, Lepimectin und Milbemectin.
17) Juvenilhormon-Analoge, z.B. Hydroprene, Kinoprene, Methoprene; oder Abamectin, Emamectin, Emamectin benzoate, Lepimectin and Milbemectin. 17) juvenile hormone analogs, eg, hydroprene, kinoprenes, methoprene; or
Fenoxycarb; Pyriproxyfen. fenoxycarb; Pyriproxyfen.
18) Wirkstoffe mit unbekannten oder nicht spezifischen Wirkmechanismen, wie beispielsweise Begasungsmittel, z.B. Methylbromid und andere Alkylhalogenide; oder Chloropicrin; Sulfurylfluorid; Borax; Brechweinstein. 18) Active ingredients with unknown or non-specific mechanisms of action, such as fumigants, e.g. Methyl bromide and other alkyl halides; or chloropicrin; sulfuryl fluoride; Borax; Tartar emetic.
19) Selektive Fraßhemmer, z.B. Pymetrozine; oder Flonicamid. 110) Milbenwachstumsinhibitoren, z.B. Clofentezine, Diflovidazin, Hexythiazox, Etoxazole. 19) Selective feeding inhibitors, e.g. pymetrozine; or flonicamide. 110) mite growth inhibitors, e.g. Clofentezine, diflovidazine, hexythiazox, etoxazole.
11 1 ) Mikrobielle Disruptoren der Insektendarmmembran, wie beispielsweise Bacillus thuringiensis Subspezies israelensis, Bacillus sphaericus, Bacillus thuringiensis Subspezies aizawai, Bacillus thuringiensis Subspezies kurstaki, Bacillus thuringiensis Subspezies tenebrionis, und BT-Pflanzen-Proteine, z.B. Cry1 Ab, Cry1 Ac, Cry1 Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34/35Ab1 . 11 1) Microbial disruptors of the insect gut membrane, such as Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis, and BT plant proteins, e.g. Cry1 Ab, Cry1 Ac, Cry1 Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34 / 35Ab1.
112) Inhibitoren der oxidativen Phosphorylierung, ATP-Disruptoren, wie beispielsweise Diafenthiuron; oder Organozinnverbindungen, z.B. Azocyclotin, Cyhexatin, Fenbutatin oxide; oder Propargite; Tetradifon. 112) inhibitors of oxidative phosphorylation, ATP disruptors such as diafenthiuron; or organotin compounds, e.g. Azocyclotine, cyhexatin, fenbutatin oxide; or propargite; Tetradifon.
113) Entkoppler der oxidativen Phoshorylierung durch Unterbrechung des H-Proton- gradienten, wie beispielsweise Chlorfenapyr und DNOC. 113) Decoupling of oxidative phosphorylation by interruption of the H proton gradient, such as chlorfenapyr and DNOC.
114) Nikotinerge Acetylcholin-Rezeptor-Antagonisten, wie beispielsweise Bensultap, Cartap (-Hydrochlorid), Thiocyclam, und Thiosultap (-sodium). 114) nicotinergic acetylcholine receptor antagonists, such as Bensultap, Cartap (hydrochloride), thiocyclam, and thiosultap (-sodium).
115) Inhibitoren der Chitinbiosynthese, Typ 0, wie beispielsweise Benzoylharnstoffe, z.B. Bistrifluron, Chlorfluazuron, Diflubenzuron, Flucycloxuron, Flufenoxuron, 115) inhibitors of chitin biosynthesis, type 0, such as benzoylureas, e.g. Bistrifluron, chlorofluorazuron, diflubenzuron, flucycloxuron, flufenoxuron,
Hexaflumuron, Lufenuron, Novaluron, Noviflumuron, Teflubenzuron und Triflumuron. Hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron.
116) Inhibitoren der Chitinbiosynthese, Typ 1 , wie beispielsweise Buprofezin.
117) Häutungsstörende Wirkstoffe, wie beispielsweise Cyromazine. 116) inhibitors of chitin biosynthesis, type 1, such as buprofezin. 117) Moisture-disrupting agents, such as cyromazines.
118) Ecdysonagonisten/-disruptoren, wie beispielsweise Diacylhydrazine, z.B. 118) ecdysone agonists / disruptors such as diacylhydrazines, e.g.
Chromafenozide, Halofenozide, Methoxyfenozide und Tebufenozide. Chromafenozide, Halofenozide, Methoxyfenozide and Tebufenozide.
119) Oktopaminerge Agonisten, wie beispielsweise Amitraz. 119) Octopaminergic agonists, such as amitraz.
120) Komplex-Ill-Elektronentransportinhibitoren, wie beispielsweise Hydramethylnon; Acequinocyl; Fluacrypyrim. 120) complex III electron transport inhibitors such as, for example, hydramethylnone; acequinocyl; Fluacrypyrim.
121 ) Komplex-I-Elektronentransportinhibitoren, beispielsweise aus der Gruppe der METI-Akarizide, z.B. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufen- pyrad, Tolfenpyrad; oder Rotenone (Derris). I22) Spannungsabhängige Natriumkanal-Blocker, z.B. Indoxacarb; Metaflumizone. 121) Complex I electron transport inhibitors, for example from the group of the METI acaricides, e.g. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad, Tolfenpyrad; or Rotenone (Derris). I22) voltage dependent sodium channel blockers, e.g. indoxacarb; Metaflumizone.
I23) Inhibitoren der Acetyl-CoA-Carboxylase, wie beispielsweise Tetronsäure- Derivate, z.B. Spirodiclofen und Spiromesifen; oder Tetramsäure-Derivate, z.B. Spirotetramat. I24) Komplex-IV-Elektronentransportinhibitoren, wie beispielsweise Phosphine, z.B. Aluminiumphosphid, Kalziumphosphid, Phosphin, Zinkphosphid; oder Cyanid. I23) inhibitors of acetyl-CoA carboxylase, such as tetronic acid derivatives, e.g. Spirodiclofen and spiromesifen; or tetramic acid derivatives, e.g. Spirotetramat. I24) complex IV electron transport inhibitors such as phosphines, e.g. Aluminum phosphide, calcium phosphide, phosphine, zinc phosphide; or cyanide.
I25) Komplex-Il-Elektronentransportinhibitoren, wie beispielsweise Cyenopyrafen. I26) Ryanodin rezeptor- Eff e kto re n , wie beispielsweise Diamide, z.B. Flubendiamide, Chiorantraniliprole (Rynaxypyr), Cyantraniiiprole (Cyazypyr) sowie 3- B ro m- N -{2- b ro m- 4-chlor-6-[(1 -cyclopropylethyl)carbamoyl]phenyl}-1 -(3-chlorpyridin-2-yl)-1 H-pyrazol-5- carboxamid (bekannt aus WO2005/077934) oder Methyl-2-[3,5-dibrom-2-({[3-brom-1 - (3-chlorpyhdin-2-yl)-1 H-pyrazol-5-yl]carbonyl}amino)benzoyl]-1 ,2- dimethylhydrazincarboxy-lat (bekannt aus WO2007/043677). I25) complex II electron transport inhibitors, such as cyenopyrafen. I26) ryanodine receptor effects, such as diamides, e.g. Flubendiamide, Chiorantraniliprole (Rynaxypyr), Cyantraniiprole (Cyazypyr) and 3-BRO m-N - {2-b ro m-4-chloro-6 - [(1-cyclopropylethyl) carbamoyl] phenyl} -1- (3-chloropyridine 2-yl) -1 H -pyrazole-5-carboxamide (known from WO2005 / 077934) or methyl 2- [3,5-dibromo-2 - ({[3-bromo-1 - (3-chloro-pyhidine-2 -yl) -1H-pyrazol-5-yl] carbonyl} amino) benzoyl] -1, 2-dimethylhydrazinecarboxylate (known from WO2007 / 043677).
Weitere Wirkstoffe mit unbekanntem Wirkmechanismus, wie beispielsweise Other drugs with unknown mechanism of action, such as
Azadirachtin, Amidoflumet, Benzoximate, Bifenazate, Chinomethionat, Cryolite, Cyflumetofen, Dicofol, 5-chloro-2-[(3,4,4-trifluorobut-3-en-1 -yl)sulfonyl]-1 ,3-thiazol, Flu-
fenerim, Pyridalyl und Pyrifluquinazon; desweiteren Präparate auf Basis von Bacillus firmus (1-1582, BioNeem, Votivo) sowie folgende bekannte wirksame Verbindungen 4- {[(6-Brompyrid-3-yl)methyl](2-fluorethyl)amino}furan-2(5H)-on (bekannt aus WO 2007/1 15644), 4-{[(6-Fluorpyrid-3-yl)methyl](2,2-difluorethyl)amino}furan-2(5H)-on (bekannt aus WO 2007/1 15644), 4-{[(2-Chlor-1 ,3-thiazol-5-yl)methyl](2- fluorethyl)amino}furan-2(5H)-on (bekannt aus WO 2007/1 15644), 4-{[(6-Chlorpyrid-3- yl)methyl](2-fluorethyl)amino}furan-2(5H)-on (bekannt aus WO 2007/1 15644), 4-{[(6- Chlorpyrid-3-yl)methyl](2,2-difluorethyl)amino}furan-2(5H)-on (bekannt aus WO Azadirachtin, amidoflumet, benzoximate, bifenazate, quinomethionate, cryolite, cyflumetofen, dicofol, 5-chloro-2 - [(3,4,4-trifluorobut-3-en-1-yl) sulfonyl] -1, 3-thiazole, Flu - fenerim, pyralidyl and pyrifluquinazone; furthermore preparations based on Bacillus firmus (1-1582, BioNeem, Votivo) and the following known active compounds 4- {[(6-bromopyrid-3-yl) methyl] (2-fluoroethyl) amino} furan-2 (5H) - on (known from WO 2007/1 15644), 4 - {[(6-fluoropyrid-3-yl) methyl] (2,2-difluoroethyl) amino} furan-2 (5H) -one (known from WO 2007/1 15644), 4 - {[(2-chloro-1,3-thiazol-5-yl) methyl] (2-fluoroethyl) amino} furan-2 (5H) -one (known from WO 2007/1 15644), 4 - {[(6-chloropyrid-3-yl) methyl] (2-fluoroethyl) amino} furan-2 (5H) -one (known from WO 2007/1 15644), 4 - {[(6-chloropyrid-3-ol) yl) methyl] (2,2-difluoroethyl) amino} furan-2 (5H) -one (known from WO
2007/1 15644), 4-{[(6-Chlor-5-fluorpyrid-3-yl)methyl](methyl)amino}furan-2(5H)-on (bekannt aus WO 2007/1 15643), 4-{[(5,6-Dichlorpyrid-3-yl)methyl](2- fluorethyl)amino}furan-2(5H)-on (bekannt aus WO 2007/1 15646), 4-{[(6-Chlor-5- fluorpyrid-3-yl)methyl](cyclopropyl)amino}furan-2(5H)-on (bekannt aus WO 2007/1 15644), 4 - {[(6-chloro-5-fluoropyrid-3-yl) methyl] (methyl) amino} furan-2 (5H) -one (known from WO 2007/1 15643), 4- {[(5,6-dichloropyrid-3-yl) methyl] (2-fluoroethyl) amino} furan-2 (5H) -one (known from WO 2007/1 15646), 4 - {[(6-chloro-5 - fluoropyrid-3-yl) methyl] (cyclopropyl) amino} furan-2 (5H) -one (known from WO
2007/1 15643), 4-{[(6-Chlorpyrid-3-yl)methyl](cyclopropyl)amino}furan-2(5H)-on (bekannt aus EP0539588), 4-{[(6-Chlorpyrid-3-yl)methyl](methyl)amino}furan-2(5H)-on (bekannt aus EP0539588), [1 -(6-Chlorpyridin-3-yl)ethyl](methyl)oxido-A4- sulfanylidencyanamid (bekannt aus WO 2007/149134) und seine Diastereomere {[(1 R)-1 -(6-Chlorpyridin-3-yl)ethyl](methyl)oxido- .6-sulfanyliden}cyanamid und {[(1 S)-1 - (6-Chlorpyridin-3-yl)ethyl](methyl)oxido- .6-sulfanyliden}cyanarnid (ebenfalls bekannt aus WO 2007/149134) sowie Sulfoxaflor (ebenfalls bekannt aus WO 2007/149134), 1 - [2-fluoro-4-methyl-5-[(2,2,2-trif!uoro 2007/1 15643), 4 - {[(6-chloropyrid-3-yl) methyl] (cyclopropyl) amino} furan-2 (5H) -one (known from EP0539588), 4 - {[(6-chloropyrid-3 -yl) methyl] (methyl) amino} furan-2 (5H) -one (known from EP0539588), [1- (6-chloropyridin-3-yl) ethyl] (methyl) oxido-A 4 -sulfanylidenecyanoanamide (known from WO 2007/149134) and its diastereomers {[(1 R) -1 - (6-chloropyridin-3-yl) ethyl] (methyl) oxido. 6- sulfanylidene} cyanamide and {[(1S) -1- (6-chloropyridin-3-yl) ethyl] (methyl) oxido. 6- sulfanylidene} cyanamide (also known from WO 2007/149134) and also sulfoxaflor (also known from WO 2007/149134), 1 - [2-fluoro-4-methyl-5 - [(2,2,2-trifluoroo
Triazol-5-amine (bekannt aus WO 2006/043635), [(3S.4aR.12R.12aS,12ßS)-3- [(Cyclopropylcarbonyl)oxy]-6,12-dihydroxy-4.12b-dimethyl-1 1-oxo-9-(pyridin-3-yl)- 1 ,3.4.4a,5.6,6a,12,12a.12ß-decahydro-2H,1 1 H-benzo[f]pyrano[4,3-b]chromen-4- yl]methylcyclopropancarboxylat (bekannt aus WO 2006/129714), 2-Cyano-3- (difluormethoxy)-N,N-dimethylbenzolsulfonamid (bekannt aus WO2006/056433), 2- Cyano-3-(difluormethoxy)-N-methylbenzolsulfonamid (bekannt aus WO2006/100288), 2-Cyano-3-(difluormethoxy)-N-ethylbenzolsulfonamid (bekannt aus WO2005/035486), 4-(Difluormethoxy)-N-ethyl-N-methyl-1 ,2-benzothiazol-3-amin-1 , 1 -dioxid (bekannt aus WO2007/057407), N-[1 -(2.3-Dimethylphenyl)-2-(3,5-dimethylphenyl)ethyl]-4,5-dihydro- 1 ,3-thiazol-2-amin (bekannt aus WO2008/104503), {1 '-[(2E)-3-(4-Chlorphenyl)prop-2- en-1 -yl]-5-fluorspiro[indol-3,4'-piperidin]-1 (2H)-yl}(2-chlorpyridin-4-yl)methanon Triazole-5-amines (known from WO 2006/043635), [(3S.4aR.12R.12aS, 12βS) -3- [(cyclopropylcarbonyl) oxy] -6,12-dihydroxy-4,12b-dimethyl-1-1 oxo-9- (pyridin-3-yl) -1,4.4.4a, 5.6,6a, 12,12a, 12β-decahydro-2H, 1: 1 H-benzo [f] pyrano [4,3-b] chromen- 4-yl] methylcyclopropanecarboxylate (known from WO 2006/129714), 2-cyano-3- (difluoromethoxy) -N, N-dimethylbenzenesulfonamide (known from WO2006 / 056433), 2-cyano-3- (difluoromethoxy) -N-methylbenzenesulfonamide (known from WO2006 / 100288), 2-cyano-3- (difluoromethoxy) -N-ethylbenzenesulfonamide (known from WO2005 / 035486), 4- (difluoromethoxy) -N-ethyl-N-methyl-1,2-benzothiazole-3 -amine-1,1-dioxide (known from WO2007 / 057407), N- [1- (2,3-dimethylphenyl) -2- (3,5-dimethylphenyl) ethyl] -4,5-dihydro-1,3-thiazole 2-amine (known from WO2008 / 104503), {1 '- [(2E) -3- (4-chlorophenyl) prop-2-en-1-yl] -5-fluorospiro [indole-3,4'- piperidine] -1 (2H) -yl} (2-chloropyridin-4-yl) methanone
(bekannt aus WO2003106457), 3-(2,5-Dimethylphenyl)-4-hydroxy-8-methoxy-1 ,8- diazaspiro[4.5]dec-3-en-2-on (bekannt aus WO2009049851 ), 3-(2,5-Dimethylphenyl)-
8-methoxy-2-oxo-1 ,8-diazaspiro[4.5]dec-3-en-4-yl-ethylcarbonat (bekannt aus (known from WO2003106457), 3- (2,5-dimethylphenyl) -4-hydroxy-8-methoxy-1,8-diazaspiro [4.5] dec-3-en-2-one (known from WO2009049851), 3- ( 2,5-dimethylphenyl) - 8-methoxy-2-oxo-1,8-diazaspiro [4.5] dec-3-en-4-yl-ethyl carbonate (known from
W 02009049851 ), 4-(But-2-in-1 -yloxy)-6-(3.5-dimethylpiperidin-1-yl)-5-fluorpyrimidin (bekannt aus WO2004099160), (2,2,3,3,4,4,5,5-Octafluorpentyl)(3,3,3- trifluorpropyl)malononitril (bekannt aus WO2005063094), (2,2,3,3,4,4,5,5- Octafluorpentyl)(3,3,4,4.4-pentafluorbutyl)malononitril (bekannt aus WO2005063094), 8-[2-(Cyclopropylmethoxy)-4-(trifluormethyl)phenoxy]-3-[6-(trifluorrnethyl)pyridazin-3- yl]-3-azabicyclo[3.2.1 ]octan (bekannt aus WO2007040280 / 282), 2-Ethyl-7-methoxy-3- methyl-6-[(2,2,3,3-tetrafluor-2,3-dihydro-1 ,4-benzodioxin-6-yl)oxy]chinolin-4-yl- methylcarbonat (bekannt aus JP20081 10953), 2-Ethyl-7-methoxy-3-methyl-6-[(2,2,3,3- tetrafluor-2,3-dihydro-1 ,4-benzodioxin-6-yl)oxy]chinolin-4-ylacetat (bekannt aus JP20081 10953), PF1364 (Chemical Abstracts Nr 1204776-60-2, bekannt aus W 02009049851), 4- (but-2-yn-1-ylxy) -6- (3,5-dimethylpiperidin-1-yl) -5-fluoropyrimidine (known from WO2004099160), (2,2,3,3,4, 4,5,5-octafluoropentyl) (3,3,3-trifluoropropyl) malononitrile (known from WO2005063094), (2,2,3,3,4,4,5,5-octafluoropentyl) (3,3,4, 4,4-pentafluorobutyl) malononitrile (known from WO2005063094), 8- [2- (cyclopropylmethoxy) -4- (trifluoromethyl) phenoxy] -3- [6- (trifluoromethyl) pyridazin-3-yl] -3-azabicyclo [3.2.1 ] octane (known from WO2007040280 / 282), 2-ethyl-7-methoxy-3-methyl-6 - [(2,2,3,3-tetrafluoro-2,3-dihydro-1,4-benzodioxin-6] yl) oxy] quinolin-4-ylmethyl carbonate (known from JP20081 10953), 2-ethyl-7-methoxy-3-methyl-6 - [(2,2,3,3-tetrafluoro-2,3-dihydroxy) 1, 4-benzodioxin-6-yl) oxy] quinolin-4-yl acetate (known from JP20081 10953), PF1364 (Chemical Abstracts No. 1204776-60-2, known from
JP2010018586), 5-[5-(3,5-Dichlorphenyl)-5-(t fluormethyl)-4.5-dihydro-1 ,2-oxazol-3- yl]-2-(1 H-1 ,2.4-triazol-1 -yl)benzonitril (bekannt aus WO2007075459), 5-[5-(2- Chlorpyridin-4-yl)-5-(trifluormethyl)-4,5-dihydro-1 .2-oxazol-3-yl]-2-(1 H-1 ,2,4-triazoM - yl)benzonitril (bekannt aus WO2007075459), 4-[5-(3.5-Dichlorphenyl)-5- (trifluormethyl)-4,5-dihydro-1 ,2-oxazol-3-yl]-2-methyl-N-{2-oxo-2-[(2,2,2- trifluorethyl)amino]ethyl}benzamid (bekannt aus WO2005085216). JP2010018586), 5- [5- (3,5-dichlorophenyl) -5- (t-fluoromethyl) -4,5-dihydro-1,2-oxazol-3-yl] -2- (1H-1, 2,4-triazole) 1 -yl) benzonitrile (known from WO2007075459), 5- [5- (2-chloropyridin-4-yl) -5- (trifluoromethyl) -4,5-dihydro-1, 2-oxazol-3-yl] -2 - (1H-1, 2,4-triazoM-yl) benzonitrile (known from WO2007075459), 4- [5- (3,5-dichlorophenyl) -5- (trifluoromethyl) -4,5-dihydro-1,2-oxazole 3-yl] -2-methyl-N- {2-oxo-2 - [(2,2,2-trifluoroethyl) amino] ethyl} benzamide (known from WO2005085216).
Safener sind vorzugsweise ausgewählt aus der Gruppe bestehend aus: Safeners are preferably selected from the group consisting of:
S1 ) Verbindungen der Formel (S1 ),
wobei die Symbole und Indizes folgende Bedeutungen haben: S1) compounds of the formula (S1), where the symbols and indices have the following meanings:
ΠΑ ist eine natürliche Zahl von 0 bis 5, vorzugsweise 0 bis 3; ΠΑ is a natural number from 0 to 5, preferably 0 to 3;
RA1 ist Halogen, (CrC4)Alkyl, (d-C4)Alkoxy, Nitro oder (d-C4)Haloalkyl; RA 1 is halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, nitro or (C 1 -C 4 ) haloalkyl;
(wA 2) (WA 4)
WA ist ein unsubstituierter oder substituierter divalenter heterocyclischer Rest aus der Gruppe der teilungesättigten oder aromatischen Fünfring-Heterocyclen mit 1 bis 3 Heteroringatomen aus der Gruppe N und O, wobei mindestens ein N-Atom und höchstens ein O-Atom im Ring enthalten ist, vorzugsweise ein Rest aus der Gruppe
(w A 2 ) (W A 4 ) WA is an unsubstituted or substituted divalent heterocyclic radical selected from the group consisting of the monounsaturated or aromatic five-membered heterocycles having 1 to 3 hetero ring atoms from the group N and O, where at least one N atom and at most one O atom are present in the ring, preferably one Rest of the group
ITIA ist 0 oder 1 ; ITIA is 0 or 1;
RA2 ist ORA3, SRA3 oder N RA3RA4 oder ein gesättigter oder ungesättigter 3- bis 7- gliedriger Heterocyclus mit mindestens einem N-Atom und bis zu 3 Heteroatomen, vorzugsweise aus der Gruppe O und S, der über das N-Atom mit der Carbonylgruppe in (S1 ) verbunden ist und unsubstituiert oder durch Reste aus der Gruppe (Ci-C4)Alkyl, (d-C4)Alkoxy oder gegebenenfalls substituiertes Phenyl substituiert ist, vorzugsweise ein Rest der Formel ORA3, N H RA4 oder N(CHa)2, insbesondere der Formel ORA3; RA 2 is ORA 3 , SRA 3 or N RA 3 RA 4 or a saturated or unsaturated 3- to 7-membered heterocycle having at least one N atom and up to 3 heteroatoms, preferably from the group O and S, via the N Atom is bonded to the carbonyl group in (S1) and is unsubstituted or substituted by radicals from the group (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy or optionally substituted phenyl, preferably a radical of the formula ORA 3 , NH RA 4 or N (CHa) 2, in particular the formula ORA 3 ;
RA3 ist Wasserstoff oder ein unsubstituierter oder substituierter aliphatischer RA 3 is hydrogen or an unsubstituted or substituted aliphatic
Kohlenwasserstoffrest, vorzugsweise mit insgesamt 1 bis 18 C- Atomen; Hydrocarbon radical, preferably having a total of 1 to 18 carbon atoms;
RA4 ist Wasserstoff,
(Ci-Ce)Alkoxy oder substituiertes oder RA 4 is hydrogen, (Ci-Ce) alkoxy or substituted or
unsubstituiertes Phenyl; unsubstituted phenyl;
RA5 ist H, (Ci-Ce)Alkyl, (Ci-C8)Haloalkyl, (Ci-C4)Alkoxy(Ci-C8)Alkyl, Cyano oder COORA9, worin RA9 Wasserstoff, (Ci-Ce)Alkyl, (Ci-C8)Haloalkyl, (Ci-C4)Alkoxy- (Ci-C4)alkyl, (Ci-C6)Hydroxyalkyl, (C3-Ci2)Cycloalkyl oder Tri-(Ci-C4)-alkyl-silyl ist;RA 5 is H, (C 1 -C 6) alkyl, (C 1 -C 8 ) haloalkyl, (C 1 -C 4 ) alkoxy (C 1 -C 8 ) alkyl, cyano or COORA 9 , in which RA 9 is hydrogen, (C 1 -C 4 ) alkyl, (Ci-C 8) haloalkyl, (Ci-C 4) alkoxy (Ci-C 4) alkyl, (Ci-C 6) hydroxyalkyl, (C3-Ci2) -cycloalkyl or tri- (Ci-C 4 ) -alkyl-silyl;
RA6, RA7, RA8 sind gleich oder verschieden Wasserstoff, (Ci-Cs)Alkyl, (d-C8)Haloalkyl, (C3-RA 6 , RA 7 , RA 8 are identical or different hydrogen, (Ci-Cs) alkyl, (dC 8 ) haloalkyl, (C 3 -
Ci2)Cycloalkyl oder substituiertes oder unsubstituiertes Phenyl; vorzugsweise: Ci2) cycloalkyl or substituted or unsubstituted phenyl; preferably:
a) Verbindungen vom Typ der Dichlorphenylpyrazolin-3-carbonsäure (S1 A), vorzugsweise Verbindungen wie 1-(2.4-Dichlorphenyl)-5-(ethoxycarbonyl)-5-methyl- 2- pyrazolin-3-carbonsäure, 1-(2,4-Dichlorphenyl)-5-(ethoxycarbonyl)-5-methyl-2- pyrazolin-3-carbonsäureethylester (S1 -1 ) ("Mefenpyr-diethyl"), und verwandte Verbin- düngen, wie sie in der WO- A-91/07874 beschrieben sind; a) compounds of the dichlorophenylpyrazoline-3-carboxylic acid (S1 A), preferably compounds such as ethyl 1- (2,4-dichlorophenyl) -5- (ethoxycarbonyl) -5-methyl-2-pyrazoline-3-carboxylic acid, 1- (2, 4-dichlorophenyl) -5- (ethoxycarbonyl) -5-methyl-2-pyrazoline-3-carboxylic acid ethyl ester (S1-1) ("mefenpyr-diethyl"), and related compounds, as described in WO-A-91 / 07874;
b) Derivate der Dichlorphenylpyrazolcarbonsäure (S 1 B), vorzugsweise Verbindungen wie 1 -(2.4-Dichlorphenyl)-5-methyl-pyrazol-3-carbonsäureethylester (S1 -2), 1 -(2,4-Di-chlorphenyl)-5-isopropyl-pyrazol-3-carbonsäureethylester (S1 -3), b) Derivatives of dichlorophenylpyrazolecarboxylic acid (S 1 B ), preferably compounds such as ethyl 1- (2,4-dichlorophenyl) -5-methylpyrazole-3-carboxylate (S1 -2), 1 - (2,4-di-chlorophenyl) -5 ethylisopropyl-pyrazole-3-carboxylate (S1-3),
1 -(2,4-Dichlor-phenyl)-5-(1 ,1 -dimethyl-ethyl)pyrazol-3-carbonsäureethyl-ester (S1 -4)
und verwandte Verbindungen, wie sie in EP-A-333 131 und EP-A-269 806 Ethyl 1 - (2,4-dichloro-phenyl) -5- (1, 1-dimethyl-ethyl) -pyrazole-3-carboxylate (S1 -4) and related compounds as described in EP-A-333,131 and EP-A-269,806
beschrieben sind; are described;
c) Derivate der 1 ,5-Diphenylpyrazol-3-carbonsäure (S1 c), vorzugsweise Verbindungen wie 1 -(2,4-Dichlorphenyl)-5-phenylpyrazol-3-carbonsäureethylester (S1 -5), 1 -(2-Chlorphenyl)-5-phenylpyrazol-3-carbonsäuremethylester (S1 -6) und verwandte Verbindungen wie sie beispielsweise in der EP-A-268554 beschrieben sind; c) derivatives of 1, 5-diphenylpyrazole-3-carboxylic acid (S1 c), preferably compounds such as 1 - (2,4-dichlorophenyl) -5-phenylpyrazole-3-carboxylate (S1 -5), 1 - (2-chlorophenyl ) -5-phenylpyrazole-3-carboxylic acid methyl ester (S1 -6) and related compounds as described, for example, in EP-A-268554;
d) Verbindungen vom Typ der Triazolcarbonsäuren (S1 d), vorzugsweise d) compounds of the type of the triazolecarboxylic acids (S1 d ), preferably
Verbindungen wie Fenchlorazol(-ethylester), d.h. Compounds such as fenchlorazole (ethyl ester), i.
1 -(2.4-Dichlorphenyl)-5-trichlormethyl-(1 H)-1 ,2.4-triazol-3-carbonsäureethylester (S1 -7), und verwandte Verbindungen wie sie in EP-A-174 562 und EP-A-346 620 beschrieben sind; 1- (2,4-dichlorophenyl) -5-trichloromethyl- (1 H) -1, 2,4-triazole-3-carboxylic acid ethyl ester (S1 -7) and related compounds as described in EP-A-174 562 and EP-A-346 620 are described;
e) Verbindungen vom Typ der 5-Benzyl- oder 5-Phenyl-2-isoxazolin-3- carbonsäure oder der 5.5-Diphenyl-2-isoxazolin-3-carbonsäure (S1 e), vorzugsweise Verbindungen wie 5-(2.4-Dichlorbenzyl)-2-isoxazolin-3-carbonsäureethylester (S1 -8) oder 5-Phenyl-2-isoxazolin-3-carbonsäureethylester (S1 -9) und verwandte Verbindungen, wie sie in WO- A-91/08202 beschrieben sind, bzw. 5,5-Diphenyl-2-isoxazoiin-3- carbonsäure (S1 -10) oder 5,5-Diphenyl-2-isoxazolin-3-carbonsäureethyiester (S1 -1 1 ) ("Isoxadifen-ethyi") oder -n-propylester (S1-12) oder der 5-(4-Fluorphenyl)-5-phenyl-2- isoxazolin-3-carbonsäureethylester (S1 -13), wie sie in der Patentanmeldung e) Compounds of the 5-benzyl- or carboxylic acid-5-phenyl-2-isoxazoline-3 or the 5.5-diphenyl-2-isoxazoline-3-carboxylic acid (S1 e), preferably compounds such as ethyl 5- (2,4-dichlorobenzyl) Ethyl 2-isoxazoline-3-carboxylate (S1 -8) or ethyl 5-phenyl-2-isoxazoline-3-carboxylate (S1 -9) and related compounds as described in WO-A-91/08202 and 5, respectively , 5-diphenyl-2-isoxazoline-3-carboxylic acid (S1 -10) or 5,5-diphenyl-2-isoxazoline-3-carboxylic acid ethyl ester (S1-1 1) ("isoxadifen-ethyl") or n-propyl ester ( S1-12) or 5- (4-fluorophenyl) -5-phenyl-2-isoxazoline-3-carboxylic acid ethyl ester (S1 -13), as described in the patent application
WO-A-95/07897 beschrieben sind. WO-A-95/07897 are described.
S2) Chinolinderivate der Formel (S2), S2) quinoline derivatives of the formula (S2)
wobei die Symbole und Indizes folgende Bedeutungen haben: where the symbols and indices have the following meanings:
RB1 ist Halogen, (Ci-C4)Alkyl, (Ci-C4)Alkoxy, Nitro oder (Ci-C4)Haloalkyl; RB 1 is halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, nitro or (C 1 -C 4 ) haloalkyl;
ne ist eine natürliche Zahl von 0 bis 5, vorzugsweise 0 bis 3; ne is a natural number of 0 to 5, preferably 0 to 3;
RB2 ist ORB 3, SRb 3 oder N RB 3RB4 oder ein gesättigter
oder ungesättigter 3- bis 7-gliedriger Heterocyclus mit mindestens einem N-Atom und bis zu 3 Heteroatomen, vorzugsweise aus der Gruppe O und S, der über das N-Atom mit der Carbonylgruppe in (S2) verbunden ist und unsubstituiert oder durch Reste aus der Gruppe (Ci-C4)Alkyl, (d-C4)Alkoxy oder gegebenenfalls substituiertes Phenyl substituiert ist, vorzugsweise ein Rest der Formel ORB3, N H RB4 oder N(CH3)2, insbesondere der Formel ORB3; RB 2 is OR B 3 , SR b 3 or NR B 3 RB 4 or a saturated one or unsaturated 3- to 7-membered heterocycle having at least one N-atom and up to 3 heteroatoms, preferably from the group O and S, which is connected via the N-atom with the carbonyl group in (S2) and unsubstituted or by radicals the group (Ci-C 4 ) alkyl, (dC 4 ) alkoxy or optionally substituted phenyl is substituted, preferably a radical of the formula ORB 3 , NH RB 4 or N (CH 3) 2, in particular the formula ORB 3 ;
RB3 ist Wasserstoff oder ein unsubstituierter oder substituierter aliphatischer Kohlenwasserstoffrest, vorzugsweise mit insgesamt 1 bis 18 C- Atomen; RB 3 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably having a total of 1 to 18 C atoms;
RB4 ist Wasserstoff, (Ci-Ce)Alkyl, (Ci-C6)Alkoxy oder substituiertes oder RB 4 is hydrogen, (Ci-Ce) alkyl, (Ci-C6) alkoxy or substituted or
unsubstituiertes Phenyl; unsubstituted phenyl;
TB ist eine (Ci oder C2)-Alkandiylkette, die unsubstituiert oder mit einem oder zwei (Ci-C4)Alkylresten oder mit [(d-C3)-Alkoxy]-carbonyl substituiert ist; vorzugsweise: TB is a (Ci or C2) -alkanediyl chain which is carbonyl unsubstituted or substituted with one or two (Ci-C 4) alkyl radicals or by [(d-C3) alkoxy]; preferably:
a) Verbindungen vom Typ der 8-Chinolinoxyessigsäure (S2a), vorzugsweisea) compounds of the type of 8-quinolinoxyacetic acid (S2 a ), preferably
(5-Chlor-8-chinolinoxy)essigsäure-(1 -methylhexyl)ester ("Cloquintocet-mexyl") (S2-1 ), (5-Chlor-8-chinolinoxy)essigsäure-(1 ,3-dimethyl-but-1-yl)ester (S2-2), (5-Chloro-8-quinolinoxy) acetic acid (1-methylhexyl) ester ("Cloquintocet-mexyl") (S2-1), (5-chloro-8-quinolinoxy) acetic acid (1,3-dimethyl-butoxy) 1-yl) ester (S2-2),
(5-Chlor-8-chinolinoxy)essigsäure-4-allyloxy-butylester (S2-3), (5-Chlor-8-chinolin- oxy)essigsäure-1 -allyloxy-prop-2-ylester (S2-4), (5-Chlor-8-chinolinoxy)essigsäure- ethylester (S2-5), (5-Chlor-8-chinolinoxy)essigsäuremethylester (S2-6), (5-Chlor-8- chinolinoxy)essigsäureallylester (S2-7), (5-Chlor-8-chinolinoxy)essigsäure-2-(2- propyliden-iminoxy)-1 -ethylester (S2-8), (5-Chlor-8-chinolinoxy)essigsäure-2-oxo-prop- 1 -ylester (S2-9) und verwandte Verbindungen, wie sie in EP-A-86 750, EP-A-94 349 und EP-A-191 736 oder EP-A-0 492 366 beschrieben sind, sowie (5-Chlor-8- chinolinoxy)essigsäure (S2-10), deren Hydrate und Salze, beispielsweise deren(5-Chloro-8-quinolinoxy) acetic acid 4-allyloxy-butyl ester (S2-3), (5-chloro-8-quinolinoxy) -acetic acid 1 -allyloxy-prop-2-yl ester (S2-4), (5-chloro-8-quinolinoxy) acetic acid ethyl ester (S2-5), (5-chloro-8-quinolinoxy) acetic acid methyl ester (S2-6), (5-chloro-8-quinolinoxy) allyl acetate (S2-7), (5-Chloro-8-quinolinoxy) acetic acid 2- (2-propylidene-iminoxy) -1-ethyl ester (S2-8), (5-chloro-8-quinolinoxy) -acetic acid 2-oxo-prop-1-yl-ester (S2-9) and related compounds as described in EP-A-86,750, EP-A-94,349 and EP-A-191,736 or EP-A-0 492 366, as well as (5-chloro-8 - quinolinoxy) acetic acid (S2-10), their hydrates and salts, for example their
Lithium-, Natrium- Kalium-, Kalzium-, Magnesium-, Aluminium-, Eisen-, Ammonium-, quartäre Ammonium-, Sulfonium-, oder Phosphoniumsalze wie sie in der WO-A- 2002/34048 beschrieben sind; Lithium, sodium, potassium, calcium, magnesium, aluminum, iron, ammonium, quaternary ammonium, sulfonium or phosphonium salts as described in WO-A-2002/34848;
b) Verbindungen vom Typ der (5-Chlor-8-chinolinoxy)malonsäure (S2b), vorzugsweise Verbindungen wie (5-Chlor-8-chinolinoxy)malonsäurediethylester, (5-Chlor- 8-chinolinoxy)malonsäurediallylester, b) compounds of the (5-chloro-8-quinolinoxy) malonic acid type (S2 b ), preferably compounds such as diethyl (5-chloro-8-quinolinoxy) malonate, (5-chloro-8-quinolinoxy) malonic acid diallyl ester,
(5-Chlor-8-chinolinoxy)malonsäure-methyl-ethylester und verwandte Verbindungen, wie sie in EP-A-0 582 198 beschrieben sind.
S3) Verbindungen der Formel (S3) (5-chloro-8-quinolinoxy) malonic acid methyl ethyl ester and related compounds as described in EP-A-0 582 198. S3) compounds of the formula (S3)
wobei die Symbole und Indizes folgende Bedeutungen haben: Rc1 ist (Ci-C4)Alkyl, (Ci-C4)Haloalkyl, (C2-C4)Alkenyl, (C2-C4)Haloalkenyl, where the symbols and indices have the following meanings: Rc 1 is (Ci-C 4) alkyl, (Ci-C 4) haloalkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) haloalkenyl,
(C3-C7)Cycloalkyl, vorzugsweise Dichlormethyl; (C3-C7) cycloalkyl, preferably dichloromethyl;
Rc2, Rc3 sind gleich oder verschieden Wasserstoff, (Ci-C4)Alkyl, (C2-C4)Alkenyl, (C2-C4)Alkinyl, (Ci-C4)Haloalkyl, (C2-C4)Haloalkenyl, (Ci-C4)Alkylcarbamoyl- (d-C4)alkyl, (C2-C4)Alkenylcarbamoyl-(CrC4)alkyl, (Ci-C4)Alkoxy-(d-C4)alkyl, Dioxolanyl-(d-C4)alkyL Thiazolyl, Furyl, Furylalkyl, Thienyl, Piperidyl, substituiertes oder unsubstituiertes Phenyl, oder Rc2 und Rc3 bilden zusammen einen substituierten oder unsubstituierten heterocyclischen Ring, vorzugsweise einen Oxazolidin-, Rc 2, rc 3 are identical or different hydrogen, (Ci-C 4) alkyl, (C2-C4) alkenyl, (C 2 -C 4) alkynyl, (Ci-C 4) haloalkyl, (C 2 -C 4 ) haloalkenyl, (Ci-C 4) alkylcarbamoyl (dC 4) alkyl, (C 2 -C 4) Alkenylcarbamoyl- (CrC 4) alkyl, (Ci-C 4) alkoxy (dC 4) alkyl, dioxolanyl (dC 4 ) alkyl, thiazolyl, furyl, furylalkyl, thienyl, piperidyl, substituted or unsubstituted phenyl, or Rc 2 and Rc 3 together form a substituted or unsubstituted heterocyclic ring, preferably an oxazolidine,
Thiazolidin-, Piperidin-, Morpholin-, Hexahydropyrimidin- oder Benzoxazinring; Thiazolidine, piperidine, morpholine, hexahydropyrimidine or benzoxazine ring;
vorzugsweise: Wirkstoffe vom Typ der Dichloracetamide, die häufig als preferably: active substances of the dichloroacetamide type, often as
Vorauflaufsafener (bodenwirksame Safener) angewendet werden, wie z. B. Pre-emergence safeners (soil-active safeners) are applied, such. B.
"Dichlormid" (N,N-Diallyl-2,2-dichloracetamid) (S3-1 ), "R-29148" (3-Dichloracetyl-2,2,5- trimethyl-1 ,3-oxazolidin) der Firma Stauffer (S3-2), "R-28725" (3-Dichloracetyl-2.2.- dimethyl-1 ,3-oxazolidin) der Firma Stauffer (S3-3), "Benoxacor" (4-Dichloracetyl-3,4- dihydro-3-methyl-2H-1 ,4-benzoxazin) (S3-4), "PPG-1292" (N-Allyl-N-[(1 ,3-dioxolan-2- yl)-methyl]-dichloracetamid) der Firma PPG Industries (S3-5). "DKA-24" (N-Allyl-N- [(allylaminocarbonyl)methyl]-dichloracetamid) der Firma Sagro-Chem (S3-6), "AD-67" oder "MON 4660" (3-Dichloracetyl-1-oxa-3-aza-spiro[4,5]decan) der Firma Nitrokemia bzw. Monsanto (S3-7), "TI-35" (1 -Dichloracetyl-azepan) der Firma TRI-Chemical RT (S3-8), "Diclonon" (Dicyclonon) oder "BAS145138" oder "LAB145138" (S3-9) ((RS)-1 - Dichloracetyl-3.3,8a-trimethylperhydropyrrolo[1 ,2-a]pyrimidin-6-on) der Firma BASF, "Furilazol" oder "MON 13900" ((RS)-3-Dichloracetyl-5-(2-furyl)-2.2-dimethyloxazolidin) (S3-10); sowie dessen (R)-Isomer (S3-1 1 ). "Dichloromid" (N, N-diallyl-2,2-dichloroacetamide) (S3-1), "R-29148" (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine) from Stauffer ( S3-2), "R-28725" (3-dichloroacetyl-2.2-dimethyl-1,3-oxazolidine) from Stauffer (S3-3), "Benoxacor" (4-dichloroacetyl-3,4-dihydro-3 -methyl-2H-1,4-benzoxazine) (S3-4), "PPG-1292" (N-allyl-N - [(1,3-dioxolan-2-yl) -methyl] -dichloroacetamide) from PPG Industries (S3-5). "DKA-24" (N-allyl-N- [(allylaminocarbonyl) methyl] -dichloroacetamide) from Sagro-Chem (S3-6), "AD-67" or "MON 4660" (3-dichloroacetyl-1-oxa 3-aza-spiro [4,5] decane) from Nitrokemia or Monsanto (S3-7), "TI-35" (1-dichloroacetyl-azepane) from TRI-Chemical RT (S3-8), " Diclonone "(dicyclonone) or" BAS145138 "or" LAB145138 "(S3-9) ((RS) -1-dichloroacetyl-3,3,8a-trimethyl-perhydropyrrolo [1,2-a] pyrimidin-6-one) from BASF," Furilazole "or" MON 13900 "((RS) -3-dichloroacetyl-5- (2-furyl) -2,2-dimethyloxazolidine) (S3-10); and its (R) isomer (S3-1 1).
S4) N-Acylsulfonamide der Formel (S4) und ihre Salze,
worin die Symbole und Indizes folgende Bedeutungen haben: XD ist CH oder N; S4) N-acylsulfonamides of the formula (S4) and their salts, wherein the symbols and indices have the following meanings: X D is CH or N;
RD1 ist CO-NRD 5RD6 oder N HCO-RD7; RD 1 is CO-NR D 5 RD 6 or N HCO-RD 7 ;
RD2 ist Halogen, (Ci-C4)Haloalkyl, (Ci-C4)Haloalkoxy, Nitro, (Ci-C4)Alkyl, RD 2 is halogen, (Ci-C 4) haloalkyl, (Ci-C 4) haloalkoxy, nitro, (Ci-C 4) alkyl,
(Ci-C4)Alkoxy, (Ci-C4)Alkylsulfonyl, (d-C4)Alkoxycarbonyl oder (Ci-C4)Alkylcarbonyl; RD3 ist Wasserstoff. (d-C4)Alkyl, (C2-C4)Alkenyl oder (C2-C4)Alkinyl; (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylsulfonyl, (C 1 -C 4 ) alkoxycarbonyl or (C 1 -C 4 ) -alkylcarbonyl; RD 3 is hydrogen. (C 1 -C 4 ) alkyl, (C 2 -C 4 ) alkenyl or (C 2 -C 4 ) alkynyl;
RD 4 ist Halogen, Nitro. (d-C4)Alkyl, (d-C4)Haloalkyl, (Ci-C4)Haloalkoxy, R D 4 is halogen, nitro. (C 1 -C 4 ) alkyl, (C 1 -C 4 ) haloalkyl, (C 1 -C 4 ) haloalkoxy,
(C3-C6)Cycloalkyl, Phenyl, (Ci-C4)Alkoxy, Cyano, (d-C )Alkylthio, (d-C4)Alkylsulfinyl, (Ci-C4)Alkylsulfonyl, (Ci-C4)Alkoxycarbonyl oder (Ci-C4)Alkylcarbonyl; (C 3 -C 6) cycloalkyl, phenyl, (Ci-C 4) alkoxy, cyano, (dC) alkylthio, (dC 4) alkylsulfinyl, (Ci-C 4) alkylsulfonyl, (Ci-C 4) alkoxycarbonyl or (C -C 4 ) alkylcarbonyl;
RD5 ist Wasserstoff, (Ci-Cc>)Alkyl, (C3-C6)Cycloalkyl. (C2-C6)Alkenyl, (C2-C6)Alkinyl, (Cs-CeJCycloalkenyl, Phenyl oder 3- bis 6-gliedriges Heterocyclyl enthaltend VD Heteroatome aus der Gruppe Stickstoff, Sauerstoff und Schwefel, wobei die sieben letztgenannten Reste durch VD Substituenten aus der Gruppe Halogen, (Ci-CejAlkoxy, (Ci-C6)Haloalkoxy, (Ci-C2)Alkylsulfinyl, (Ci-C2)Alkylsulfonyl, (C3-C6)Cycloalkyl, (d- C4)Alkoxycarbonyl, (d-C4)Alkylcarbonyl und Phenyl und im Falle cyclischer Reste auch (Ci-C4) Alkyl und (d-C4)Haloalkyl substituiert sind; RD 5 is hydrogen, (Ci-Cc > ) alkyl, (C3-C 6 ) cycloalkyl. (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (Cs-CeJCycloalkenyl, phenyl or 3- to 6-membered heterocyclyl containing VD heteroatoms from the group consisting of nitrogen, oxygen and sulfur, wherein the latter seven radicals by VD substituents from the group halogen, (Ci-CejAlkoxy, (Ci-C 6) haloalkoxy, (Ci-C2) alkylsulfinyl, (Ci-C2) alkylsulfonyl, (C 3 -C 6) cycloalkyl, (d- C4 ) Alkoxycarbonyl, (dC 4 ) alkylcarbonyl and phenyl and in the case of cyclic radicals also (Ci-C 4 ) alkyl and (dC 4 ) haloalkyl are substituted;
RD 6 ist Wasserstoff, (CrC6)Alkyl, (C2-C6)Alkenyl oder (C2-C6)Alkinyl, wobei die drei letztgenannten Reste durch VD Reste aus der Gruppe Halogen, Hydroxy, (d-C4)Alkyl, (Ci-C4)Alkoxy und (Ci-C4)Alkylthio substituiert sind, oder R D 6 is hydrogen, (C 1 -C 6 ) alkyl, (C 2 -C 6 ) alkenyl or (C 2 -C 6 ) alkynyl, where the last three radicals are represented by VD radicals from the group consisting of halogen, hydroxy, (C 1 -C 4 ) alkyl , (Ci-C 4 ) alkoxy and (Ci-C 4 ) alkylthio are substituted, or
RD5 und RD6 gemeinsam mit dem dem sie tragenden Stickstoffatom einen Pyrrolidinyl- oder Piperidinyl-Rest bilden; RD 5 and RD 6 together with the nitrogen atom carrying them form a pyrrolidinyl or piperidinyl radical;
RD 7 ist Wasserstoff, (Ci-C4)Alkylamino, Di-(Ci-C4)alkylamino, (CrC6)Alkyl, R D 7 is hydrogen, (Ci-C 4) alkylamino, di (Ci-C 4) alkylamino, (CrC 6) alkyl,
(Ca-CeJCycloalkyl, wobei die 2 letztgenannten Reste durch VD Substituenten aus der Gruppe Halogen, (Ci-C4)Alkoxy, (Ci-C6)Haloalkoxy und (Ci-C4)Alkylthio und im Falle cyclischer Reste auch (d-C4)Alkyl und (d-C4)Haloalkyl substituiert sind; (Ca-CeJCycloalkyl, where the 2 latter radicals by VD substituents selected from the group consisting of halogen, (Ci-C 4 ) alkoxy, (Ci-C6) haloalkoxy and (Ci-C 4 ) alkylthio and in the case of cyclic radicals also (dC 4 ) Alkyl and (dC 4 ) haloalkyl;
no ist 0, 1 oder 2; no is 0, 1 or 2;
mo ist 1 oder 2;
VD ist 0, 1 , 2 oder 3; davon bevorzugt sind Verbindungen vom Typ der N-Acylsulfonamide, z.B. mo is 1 or 2; VD is 0, 1, 2 or 3; Of these, preference is given to compounds of the N-acylsulfonamide type, for example
nachfolgenden Formel (S4a), die z. B. bekannt sind aus WO-A-97/45016 the following formula (S4 a ), the z. B. are known from WO-A-97/45016
worin wherein
RD7 (Ci-Ce)Alkyl, (C3-C6)Cycloalkyl, wobei die 2 letztgenannten Reste durch VD Substituenten aus der Gruppe Halogen, (Ci-C4)Alkoxy, (Ci-C6)Haloalkoxy und (Ci-RD 7 (C 1 -C 6) -alkyl, (C 3 -C 6) -cycloalkyl, where the 2 last-mentioned radicals are represented by VD substituents from the group consisting of halogen, (C 1 -C 4 ) -alkoxy, (C 1 -C 6) -haloalkoxy and
C4)Alkylthio und im Falle cyclischer Reste auch (d-C4)Alkyl und (d-C4)Haloalkyl substituiert sind; C 4 ) alkylthio and in the case of cyclic radicals also (C 1 -C 4 ) alkyl and (C 1 -C 4 ) haloalkyl;
RD4 Halogen, (Ci-C4)Alkyl, (CrC4)Alkoxy, CF3; RD 4 is halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, CF 3;
mo 1 oder 2; mo 1 or 2;
VD ist 0, 1 , 2 oder 3 bedeutet; sowie Acylsulfamoyibenzoesaureamide, z.B. der nachfolgenden Formel (S4b), die z.B. bekannt sind aus WO- A-99/ 16744, VD is 0, 1, 2 or 3; and Acylsulfamoyibenzoesaureamide, for example of the formula (S4 b), for example are known from WO-A-99/16744,
z.B. solche worin eg those in which
RD5 = Cyclopropyl und (RD4) = 2-OMe ist ("Cyprosulfamide", S4-1 ), RD 5 = cyclopropyl and (RD 4 ) = 2-OMe ("Cyprosulfamide", S4-1),
RD5 = Cyclopropyl und (RD4) = 5-CI-2-OMe ist (S4-2), RD 5 = cyclopropyl and (RD 4 ) = 5-CI-2-OMe is (S4-2),
RD5 = Ethyl und (RD4) = 2-OMe ist (S4-3), RD 5 = ethyl and (RD 4 ) = 2-OMe is (S4-3),
RD5 = Isopropyl und (RD4) = 5-CI-2-OMe ist (S4-4) und RD 5 = isopropyl and (RD 4 ) = 5-CI-2-OMe is (S4-4) and
RD 5 = Isopropyl und (RD4) = 2-OMe ist (S4-5). sowie Verbindungen vom Typ der N-Acylsulfamoylphenylharnstoffe der Formel (S4C), die z.B. bekannt sind aus der EP-A-365484,
worin R D 5 = isopropyl and (RD 4 ) = 2-OMe is (S4-5). and also compounds of the type of the N-acylsulfamoylphenylureas of the formula (S 4 C ) which are known, for example, from EP-A-365484, wherein
RD8 und RD9 unabhängig voneinander Wasserstoff, (Ci-Ce)Alkyl, (Ca-CsJCycloalkyl,RD 8 and RD 9 independently of one another are hydrogen, (C 1 -C 6) alkyl, (C 1 -C 5 -cycloalkyl,
(C3-C6)Alkenyl, (C3-C6)Alkinyl, (C 3 -C 6 ) alkenyl, (C 3 -C 6 ) alkynyl,
RD4 Halogen, (Ci-C4)Alkyl, (Ci-C4)Alkoxy, CF3 RD 4 halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, CF 3
rriD 1 oder 2 bedeutet; beispielsweise triD is 1 or 2; for example
1 -[4-(N-2-Methoxybenzoylsulfamoyl)phenyl]-3-methylharnstoff, 1 - [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3-methylurea,
1 -[4-(N-2-Methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylharnstoff. 1 - [4- (N-2-Methoxybenzoylsulfamoyl) phenyl] -3,3-dimethylurea.
1 -[4-(N-4,5-Dimethylbenzoylsulfamoyl)phenyl]-3-methylharnstoff. S5) Wirkstoffe aus der Klasse der Hydroxyaromaten und der aromatisch- aliphatischen Carbonsäurederivate (S5), z.B. 3,4.5-Triacetoxybenzoesäureethylester, 3.5-Di-methoxy-4-hydroxybenzoesäure, 3,5-Dihydroxybenzoesäure, 4- Hydroxysalicylsäure, 4-Fluorsalicyclsäure, 2-Hydroxyzimtsäure, 2,4-Dichlorzimtsäure, wie sie in der WO-A-2004/084631 , WO-A-2005/015994, WO-A-2005/016001 beschrieben sind. 1 - [4- (N-4,5-dimethylbenzoylsulfamoyl) phenyl] -3-methylurea. S5) Active ingredients from the class of hydroxyaromatics and aromatic-aliphatic carboxylic acid derivatives (S5), e.g. 3,4,5-triacetoxybenzoic acid ethyl ester, 3,5-di-methoxy-4-hydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 4-hydroxysalicylic acid, 4-fluorosalicyclic acid, 2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid, as described in WO-A-2004 / No. 084631, WO-A-2005/015994, WO-A-2005/016001.
56) Wirkstoffe aus der Klasse der 1 ,2-Dihydrochinoxalin-2-one (S6), z.B. 56) Agents from the class of 1, 2-dihydroquinoxaline-2-ones (S6), e.g.
1 -Methyl-3-(2-thienyl)-1 ,2-dihydrochinoxalin-2-on, 1-Methyl-3-(2-thienyl)-1 .2-dihydro- chinoxalin-2-thion, 1 -(2-Aminoethyl)-3-(2-thienyl)-1 ,2-dihydro-chinoxalin-2-on-hydro- chlorid, 1-(2-Methylsulfonylaminoethyl)-3-(2-thienyl)-1 ,2-dihydrochinoxa-lin-2-on, wie sie in der WO-A-2005/1 12630 beschrieben sind. 1-Methyl-3- (2-thienyl) -1,2-dihydroquinoxalin-2-one, 1-methyl-3- (2-thienyl) -1,2-dihydroquinoxaline-2-thione, 1 - (2 Aminoethyl) -3- (2-thienyl) -1,2-dihydroquinoxalin-2-one hydrochloride, 1- (2-methylsulfonylaminoethyl) -3- (2-thienyl) -1,2-dihydroquinoxa lin-2-one, as described in WO-A-2005/1 12630.
57) Verbindungen der Formel (S7).wie sie in der WO-A-1998/38856 beschrieben 57) Compounds of the formula (S7), as described in WO-A-1998/38856
sind worin die Symbole und Indizes folgende Bedeutungen haben: RE1 , RE2 sind unabhängig voneinander Halogen, (Ci-C4)Alkyl, (Ci-C4)Alkoxy, are where the symbols and indices have the following meanings: RE 1, RE 2 are independently halogen, (Ci-C 4) alkyl, (Ci-C 4) alkoxy,
(CrC4)Haloalkyl, (Ci-C4)Alkylamino, Di-(Ci-C4)Alkylamino, Nitro; (C 1 -C 4 ) haloalkyl, (C 1 -C 4 ) alkylamino, di- (C 1 -C 4 ) alkylamino, nitro;
AE ist COORE3 oder COSRE4 A E is COORE 3 or COSRE 4
RE3, RE4 sind unabhängig voneinander Wasserstoff, (d-C4)Alkyl, (C2-Ce)Alkenyl, (C2-C4)Alkinyl, Cyanoalkyl, (Ci-C4)Haloalkyl, Phenyl, Nitrophenyl, Benzyi, Halobenzyl, Pyridinylalkyl und Alkylammonium, RE 3 , RE 4 are independently hydrogen, (C 1 -C 4 ) alkyl, (C 2 -C 6) alkenyl, (C 2 -C 4 ) alkynyl, cyanoalkyl, (C 1 -C 4 ) haloalkyl, phenyl, nitrophenyl, benzyl, halobenzyl, pyridinylalkyl and alkyl ammonium,
ΠΕ1 ist 0 oder 1 ΠΕ 1 is 0 or 1
ΠΕ2, ΠΕ3 sind unabhängig voneinander 0, 1 oder 2, vorzugsweise Diphenylmethoxyessigsäure, Diphenylmethoxyessigsäureethylester, Diphenyl-methoxyessigsäuremethylester (CAS-Reg.Nr. 41858-19-9) (S7-1 ). ΠΕ 2 , ΠΕ 3 are each independently 0, 1 or 2, preferably diphenylmethoxyacetic acid, ethyl diphenylmethoxyacetate, methyl diphenylmethoxyacetate (CAS Reg. No. 41858-19-9) (S7-1).
S8) Verbindungen der Formel (S8),wie sie in der WO-A-98/27049 beschrieben sind S8) compounds of the formula (S8) as described in WO-A-98/27049
Worin
Wherein
nF für den Fall, dass XF=N ist, eine ganze Zahl von 0 bis 4 und nF for the case that XF = N, an integer from 0 to 4 and
für den Fall, dass XF=CH ist, eine ganze Zahl von 0 bis 5 , for the case that XF = CH, an integer from 0 to 5,
RF1 Halogen, (Ci-C4)Alkyl, (Ci-C4)Haloalkyl, (Ci-C4)Alkoxy, (Ci-C4)Haloalkoxy, Nitro, (Ci-C4)Alkylthio, (Ci-C4)-Alkylsulfonyl, (d-C4)Alkoxycarbonyl, ggf. substituiertes. Phenyl, ggf. substituiertes Phenoxy, RF 1 halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) haloalkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) haloalkoxy, nitro, (C 1 -C 4 ) alkylthio, (C 1 -C 4 ) 4 ) -alkylsulfonyl, (dC 4 ) alkoxycarbonyl, optionally substituted. Phenyl, optionally substituted phenoxy,
RF2 Wasserstoff oder (Ci-C4)Alkyl RF 2 is hydrogen or (Ci-C 4 ) alkyl
RF3 Wasserstoff, (Ci-Ce)Alkyl, (C2-C4)Alkenyl, (C2-C4)Alkinyl, oder Aryl, wobei jeder der vorgenannten C-haltigen Reste unsubstituiert oder durch einen oder mehrere,
vorzugsweise bis zu drei gleiche oder verschiedene Reste aus der Gruppe, bestehend aus Halogen und Alkoxy substituiert ist; bedeuten, oder deren Salze, vorzugsweise Verbindungen worin
RF 3 is hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 4 ) -alkenyl, (C 2 -C 4 ) -alkynyl, or aryl, where each of the abovementioned C-containing radicals is unsubstituted or substituted by one or more preferably up to three identical or different radicals from the group consisting of halogen and alkoxy substituted; or their salts, preferably compounds wherein
np eine ganze Zahl von 0 bis 2 , np is an integer from 0 to 2,
RF1 Halogen, (Ci-C4)Alkyl, (Ci-C4)Haloalkyl, (Ci-C4)Alkoxy, (Ci-C4)Haloalkoxy, RF2 Wasserstoff oder (Ci-C4)Alkyl, RF 1 is halogen, (Ci-C 4) alkyl, (Ci-C 4) haloalkyl, (Ci-C 4) alkoxy, (Ci-C 4) haloalkoxy, RF 2 is hydrogen or (Ci-C 4) alkyl,
RF3 Wasserstoff, (Ci-C8)Alkyl, (C2-C4)Alkenyl, (C2-C4)Alkinyl, oder Aryl, wobei jeder der vorgenannten C-haltigen Reste unsubstituiert oder durch einen oder mehrere, vorzugsweise bis zu drei gleiche oder verschiedene Reste aus der Gruppe, bestehend aus Halogen und Alkoxy substituiert ist, bedeuten, RF 3 is hydrogen, (Ci-C 8 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, or aryl, wherein each of the aforementioned C-containing radicals unsubstituted or by one or more, preferably is substituted to three identical or different radicals from the group consisting of halogen and alkoxy,
oder deren Salze. or their salts.
S9) Wirkstoffe aus der Klasse der 3-(5-Tetrazolylcarbonyl)-2-chinolone (S9), z.B. 1 .2-Dihydro-4-hydroxy-1 -ethyl-3-(5-tetrazolylcarbonyl)-2-chinolon (CAS-Reg.Nr. S9) Agents from the class of 3- (5-tetrazolylcarbonyl) -2-quinolones (S9), e.g. 1-.2-dihydro-4-hydroxy-1-ethyl-3- (5-tetrazolylcarbonyl) -2-quinolone (CAS Reg.
219479-18-2), 1 ,2-Dihydro-4-hydroxy-1 -methyl-3-(5-tetrazolyl-carbonyl)-2-chinolon (CAS-Reg.Nr. 95855-00-8), wie sie in der WO-A-1999/000020 beschrieben sind. 219479-18-2), 1, 2-dihydro-4-hydroxy-1-methyl-3- (5-tetrazolyl-carbonyl) -2-quinolone (CAS Reg. 95855-00-8), as described in WO-A-1999/000020.
S10) Verbindungen der Formeln (S10a) oder (S10 ) S10) compounds of the formulas (S10 a ) or (S10)
wie sie in der WO-A-2007/023719 und WO-A-2007/023764 beschrieben sind as described in WO-A-2007/023719 and WO-A-2007/023764
RG1 Halogen, (d-C4)Alkyl, ethoxy, Nitro, Cyano, CF3, OCF3 RG 1 halogen, (C 1 -C 4 ) alkyl, ethoxy, nitro, cyano, CF 3 , OCF 3
YG, ZGunabhängig voneinander O oder S, YG, ZGindependently O or S,
ησ eine ganze Zahl von 0 bis 4, ησ is an integer from 0 to 4,
RG 2 (Ci-Cie)Alkyl, (C2-C6)Alkenyl, (C3-C6)Cycloalkyl, Aryl; Benzyl, Halogenbenzyl,
RG3 Wasserstoff oder (Ci-Ce)Alkyl bedeutet. R G 2 (C 1 -C 6 ) alkyl, (C 2 -C 6 ) alkenyl, (C 3 -C 6 ) cycloalkyl, aryl; Benzyl, halobenzyl, RG 3 is hydrogen or (Ci-Ce) alkyl.
51 1 ) Wirkstoffe vom Typ der Oxyimino- Verbindungen (S1 1 ), die als Saatbeizmittel bekannt sind, wie z. B. "Oxabetrinil" ((Z)-1 ,3-Dioxolan-2-ylmethoxyimino- (phenyl)acetonitril) (S1 1 -1 ), das als Saatbeiz-Safener für Hirse gegen Schäden von Metoiachlor bekannt ist, "Fluxofenim" (1 -(4-Chlorphenyl)-2.2.2-trifluor-1 -ethanon-0- (1 ,3-dioxolan-2-ylmethyl)-oxim) (S1 1 -2), das als Saatbeiz-Safener für Hirse gegen Schäden von Metoiachlor bekannt ist, und "Cyometrinil" oder "CGA-43089" ((Z)- Cyanomethoxyimino(phenyl)acetonitril) (S1 1 -3), das als Saatbeiz-Safener für Hirse gegen Schäden von Metoiachlor bekannt ist. 51 1) active substances of the type of oxyimino compounds (S1 1), which are known as seed dressings, such as. "Oxabetrinil" ((Z) -1, 3-dioxolan-2-ylmethoxyimino- (phenyl) acetonitrile) (S1 1 -1), which is known as seed safener for millet against damage by metoiachlor, "Fluxofenim" ( 1- (4-chlorophenyl) -2,2,2-trifluoro-1-ethanone-O- (1,3-dioxolan-2-ylmethyl) oxime) (S1 1 -2), which was used as a seed dressing safener for millet against damage of metoiachlor, and "Cyometrinil" or "CGA-43089" ((Z) - cyanomethoxyimino (phenyl) acetonitrile) (S1 1 -3), which is known as a seed dressing safener for millet against damage by metoiachlor.
512) Wirkstoffe aus der Klasse der Isothiochromanone (S12), wie z.B. Methyl-[(3- oxo-1 H-2-benzothiopyran-4(3H)-yliden)methoxy]acetat (CAS-Reg.Nr. 205121 -04-6) (S12-1 ) und verwandte Verbindungen aus WO-A-1998/13361 . 512) Isothiochromanone (S12) class agents, e.g. Methyl - [(3-oxo-1H-2-benzothiopyran-4 (3H) -ylidene) methoxy] acetate (CAS Reg. No. 205121 -04-6) (S12-1) and related compounds of WO-A -1998/13361.
513) Eine oder mehrere Verbindungen aus Gruppe (S13): "Naphthalic anhydrid" (1 ,8-Naphthalindicarbonsäureanhydrid) (S13-1 ), das als Saatbeiz-Safener für Mais gegen Schäden von Thiocarbamatherbiziden bekannt ist, "Fenclorim" (4,6-Dichlor-2- phenylpyrimidin) (S13-2), das als Safener für Pretilachlor in gesätem Reis bekannt ist, "Flurazole" (Benzyl-2-chlor-4-trifluormethyl-1.3-thiazol-5-carboxylat) (S13-3), das als Saatbeiz-Safener für Hirse gegen Schäden von Alachior und Metoiachlor bekannt ist, "CL 304415" (CAS-Reg.Nr. 31541 -57-8) (4-Carboxy-3,4-dihydro-2H-1-benzopyran-4- essigsäure) (S13-4) der Firma American Cyanamid, das als Safener für Mais gegen Schäden von Imidazolinonen bekannt ist, "MG 191 " (CAS-Reg.Nr. 96420-72-3) (2- Dichlormethyl-2-methyl-1 ,3-dioxolan) (S13-5) der Firma Nitrokemia, das als Safener für Mais bekannt ist, "MG-838" (CAS-Reg.Nr. 133993-74-5) (2-propenyl 1-oxa-4- azaspiro[4.5]decan-4-carbodithioat) (S13-6) der Firma Nitrokemia, "Disuifoton" (0.0- Diethyl S-2-ethylthioethyl phosphordithioat) (S13-7), "Dietholate" (0,0-Diethyl-O- phenylphosphorothioat) (S13-8), "Mephenate" (4-Chlorphenyl-methylcarbamat) (S13-9). 513) One or more compounds of group (S13): "naphthalene anhydride" (1,8-naphthalenedicarboxylic anhydride) (S13-1), known as a seed safener for corn against damage by thiocarbamate herbicides, "fenclorim" (4,6 Dichloro-2-phenylpyrimidine) (S13-2) known as safener for pretilachlor in seeded rice, "flurazole" (benzyl-2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate) (S13-3 ), which is known as millet safener for millet against damages of alachior and metoiachlor, "CL 304415" (CAS No. 31541-57-8) (4-carboxy-3,4-dihydro-2H-1) benzopyran-4-acetic acid) (S13-4) from American Cyanamid, which is known as a safener for corn against damage of imidazolinones, "MG 191" (CAS Reg. No. 96420-72-3) (2-dichloromethyl- 2-methyl-1,3-dioxolane) (S13-5) from Nitrokemia, which is known as safener for corn, "MG-838" (CAS Reg. No. 133993-74-5) (2-propenyl 1 -oxa-4-azaspiro [4.5] decane-4-carbodithioate) (S13-6) from Nitrokemia, "Disuifoton" (0.0- Die ethyl S-2-ethylthioethyl phosphorodithioate) (S13-7), "dietholate" (0,0-diethyl-O-phenylphosphorothioate) (S13-8), "mephenate" (4-chlorophenyl-methylcarbamate) (S13-9).
514) Wirkstoffe, die neben einer herbiziden Wirkung gegen Schadpflanzen auch Safenerwirkung an Kulturpflanzen wie Reis aufweisen, wie z. B. 514) active substances which, in addition to a herbicidal activity against harmful plants, also have safener action on crops such as rice, such as, for example, rice. B.
"Dimepiperate" oder "MY-93" (S-1 -Methyl-1 -phenylethyl-piperidin-1 -carbothioat), das
als Safener für Reis gegen Schäden des Herbizids olinate bekannt ist, "Daimuron" oder "SK 23" (1 -(1 -Methyl-1 -phenylethyl)-3-p-tolyl-harnstoff), das als Safener für Reis gegen Schäden des Herbizids Imazosulfuron bekannt ist, "Cumyluron" = "JC-940" (3- (2-Chlorphenylmethyl)-1 -(1 -methyl-1-phenyl-ethyl)harnstoff, siehe JP-A-60087254), das als Safener für Reis gegen Schäden einiger Herbizide bekannt ist, "Dimepiperate" or "MY-93" (S-1-methyl-1-phenylethyl-piperidine-1-carbothioate), the as a safener for rice against damage of the herbicide olinate is known, "daimurone" or "SK 23" (1- (1-methyl-1-phenylethyl) -3-p-tolyl-urea), which is used as a safener for rice against damage of the Herbicide imazosulfuron is known, "Cumyluron" = "JC-940" (3- (2-chlorophenylmethyl) -1 - (1-methyl-1-phenyl-ethyl) urea, see JP-A-60087254), which as safeners for Rice is known against damage of some herbicides
"Methoxyphenon" oder "NK 049" (3,3'-Dimethyl-4-methoxy-benzophenon), das als Safener für Reis gegen Schäden einiger Herbizide bekannt ist, "CSB" (1 -Brom-4- (chlormethylsulfonyl)benzol) von Kumiai, (CAS-Reg.Nr. 54091 -06-4), das als Safener gegen Schäden einiger Herbizide in Reis bekannt ist. "Methoxyphenone" or "NK 049" (3,3'-dimethyl-4-methoxybenzophenone) known as safener for rice against damage of some herbicides "COD" (1-Bromo-4- (chloromethylsulfonyl) benzene) by Kumiai, (CAS No. 54091 -06-4), known as safener against damage of some herbicides in rice.
S15) Verbindungen der Formel (S15) oder deren Tautomere S15) compounds of the formula (S15) or their tautomers
wie sie in der WO-A-2008/131861 und WO-A-2008/131860 beschrieben sind as described in WO-A-2008/131861 and WO-A-2008/131860
worin RH1 einen (d-CeJHaloalkylrest bedeutet und wherein RH 1 represents a (d-CeJHaloalkylrest and
RH2 Wasserstoff oder Halogen bedeutet und RH 2 is hydrogen or halogen and
RH3, RH4 unabhängig voneinander Wasserstoff, (Ci-Cie)Alkyl, (C2-Cie)Alkenyl oder (C2-Cie)Alkinyl, wobei jeder der letztgenannten 3 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Cyano, (Ci-C4)Alkoxy, (Ci-C4)Haloalkoxy, (Ci-C4)Alkylthio, (Ci-C4)Alkylamino, Di[(Ci-C4)alkyl]-amino, R 3 , R 4 independently of one another are hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl or (C 2 -C 6) -alkynyl, where each of the last-mentioned 3 radicals is unsubstituted or is replaced by one or more radicals from the group consisting of halogen, hydroxyl, cyano, (Ci-C 4) alkoxy, (Ci-C 4) haloalkoxy, (Ci-C 4) alkylthio, (Ci-C 4) alkylamino, di [(Ci-C 4) alkyl] amino,
[(Ci-C4)Alkoxy]-carbonyl, [(Ci-C4)Haloalkoxy]-carbonyl, (C3-C6)Cycloalkyl, das unsubstituiert oder substituiert ist, Phenyl, das unsubstituiert oder substituiert ist, und Heterocyclyl, das unsubstituiert oder substituiert ist, substituiert ist, oder (C3- CeJCycloalkyl, (C4-C6)Cycloalkenyl, (Ca-Cc Cycloalkyl, das an einer Seite des Rings mit einem 4 bis 6-gliedrigen gesättigten oder ungesättigten carbocyclischen Ring kondensiert ist, oder (C4-C6)Cycloalkenyl, das an einer Seite des Rings mit einem 4 bis 6-gliedrigen gesättigten oder ungesättigten carbocyclischen Ring kondensiert ist, wobei jeder der letztgenannten 4 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Cyano, (C1 -C4)Alkyl, (C1 -C4)Haloalkyl, (C1 -C4)Alkoxy, (C1 -C4)Haloalkoxy, (C1 -C4)Alkylthio, (C1 -C4)Alkylamino, Di[(C1 -
C4)alkyl]-amino, [(C1 -C4)Alkoxy]-carbonyl, [(C1 -C4)Haloalkoxy]-carbonyl, [(C 1 -C 4 ) alkoxy] carbonyl, [(C 1 -C 4 ) haloalkoxy] carbonyl, (C 3 -C 6) cycloalkyl which is unsubstituted or substituted, phenyl which is unsubstituted or substituted, and heterocyclyl which is unsubstituted or (C 3 -C 12) cycloalkyl, (C 4 -C 6) cycloalkenyl, (C 1 -C 6 -cycloalkyl which is fused on one side of the ring with a 4 to 6-membered saturated or unsaturated carbocyclic ring, or ( C 4 -C 6) cycloalkenyl which is fused on one side of the ring with a 4 to 6-membered saturated or unsaturated carbocyclic ring, each of the last 4 radicals unsubstituted or by one or more radicals selected from the group halogen, hydroxy, cyano, (C1-C4) alkyl, (C1-C4) haloalkyl, (C1-C4) alkoxy, (C1-C4) haloalkoxy, (C1-C4) alkylthio, (C1-C4) alkylamino, di [(C1- C4) alkyl] amino, [(C1-C4) alkoxy] carbonyl, [(C1-C4) haloalkoxy] carbonyl,
(C3-C6)Cycloalkyl, das unsubstituiert oder substituiert ist, Phenyl, das unsubstituiert oder substituiert ist, und Heterocyclyl, das unsubstituiert oder substituiert ist, substituiert ist, bedeutet oder (C 3 -C 6) cycloalkyl which is unsubstituted or substituted, phenyl which is unsubstituted or substituted, and heterocyclyl which is unsubstituted or substituted, or denotes
RH3 (Ci-C4)-Alkoxy, (C2-C4)Alkenyloxy, (C2-C6)Alkinyloxy oder (C2-C )Haloalkoxy bedeutet und RH 3 is (C 1 -C 4 ) alkoxy, (C 2 -C 4 ) alkenyloxy, (C 2 -C 6 ) alkynyloxy or (C 2 -C) haloalkoxy and
RH4 Wasserstoff oder (Ci-C4)-Alkyl bedeutet oder RH 4 is hydrogen or (C 1 -C 4 ) -alkyl or
RH3 und RH4 zusammen mit dem direkt gebundenen N-Atom einen vier- bis achtgliedrigen RH 3 and RH 4 together with the directly attached N atom form a four- to eight-membered one
heterocyclischen Ring, der neben dem N-Atom auch weitere Heteroringatome, vorzugsweise bis zu zwei weitere Heteroringatome aus der Gruppe N, O und S enthalten kann und der unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Cyano, Nitro, (d-C4)Alkyl, (Ci-C4)Haloalkyl, (d-C4)Alkoxy, (Ci- C4)Haloalkoxy und (d-C4)Alkylthio substituiert ist, bedeutet. heterocyclic ring which may contain in addition to the N-atom also further hetero ring atoms, preferably up to two further hetero ring atoms from the group N, O and S and unsubstituted or by one or more radicals from the group halogen, cyano, nitro, (dC 4 ) alkyl, (Ci-C 4) haloalkyl, (dC 4) alkoxy, (Ci C 4) haloalkoxy and (dC 4) alkylthio means.
S16) Wirkstoffe, die vorrangig als Herbizide eingesetzt werden, jedoch auch Safenerwirkung auf Kulturpflanzen aufweisen, z.B. (2.4-Dichlorphenoxy)essigsäure (2,4-D), (4-Chlorphenoxy)essigsäure, (R,S)-2-(4-Chlor-o-tolyloxy)propionsäure (Mecoprop), 4-(2,4-Dichlorphenoxy)buttersäure (2,4-DB), (4-Chlor-o-tolyloxy)- essigsäure (MCPA), 4-(4-Chlor-o-tolyloxy)buttersäure, 4-(4-Chlorphenoxy)- buttersäure, 3,6-Dichlor-2-methoxybenzoesäure (Dicamba), 1 -(Ethoxycarbonyl)ethyl- 3,6-dichlor-2-methoxybenzoat (Lactidichlor-ethyl).
S16) active substances, which are used primarily as herbicides, but also safener action on crop plants, eg (2,4-dichlorophenoxy) acetic acid (2,4-D), (4-chlorophenoxy) acetic acid, (R, S) -2- (4 Chloro-o-tolyloxy) propionic acid (mecoprop), 4- (2,4-dichlorophenoxy) butyric acid (2,4-DB), (4-chloro-o-tolyloxy) acetic acid (MCPA), 4- (4- Chloro-o-tolyloxy) butyric acid, 4- (4-chlorophenoxy) butyric acid, 3,6-dichloro-2-methoxybenzoic acid (Dicamba), 1 - (ethoxycarbonyl) ethyl-3,6-dichloro-2-methoxybenzoate (lactic dichloro) ethyl).
Pflanzenreife beeinflussende Stoffe: Plant-maturing substances:
Als Kombinationspartner für die Verbindungen der allgemeinen Formel (I) in As a combination partner for the compounds of general formula (I) in
Mischungsformulierungen oder im Tank-Mix sind beispielsweise bekannte Wirkstoffe, die auf einer Inhibition von beispielsweise 1-Aminocyclopropan-1 -carboxylatsynthase, 1 -aminocyclopropane-1 -carboxylatoxidase und den Ethylenrezeptoren, z. B. ETR1 , ETR2, ERS1 , ERS2 oder EIN4, beruhen, einsetzbar, wie sie z. B. in Biotechn. Adv. 2006, 24, 357-367; Bot. Bull. Acad. Sin. 199, 40, 1 -7 oder Plant Growth Reg. 1993, 13, 41 -46 und dort zitierter Literatur beschrieben sind. Mixture formulations or in the tank mix are, for example, known active compounds which are based on an inhibition of, for example, 1-aminocyclopropane-1-carboxylate synthase, 1-aminocyclopropane-1-carboxylate oxidase and the ethylene receptors, eg. As ETR1, ETR2, ERS1, ERS2 or EIN4, are based, can be used as z. B. in biotechnology. Adv. 2006, 24, 357-367; Bot. Bull. Acad. Sin. 199, 40, 1-7 or Plant Growth Reg. 1993, 13, 41-46 and references cited therein.
Als bekannte die Pflanzenreife beeinflussende Stoffe, die mit den Verbindungen der allgemeinen Formel (I) kombiniert werden können, sind z.B. folgende Wirkstoffe zu nennen (die Verbindungen sind entweder mit dem "common name" nach der As known plant ripening affecting substances which can be combined with the compounds of the general formula (I) are e.g. to name the following active ingredients (the compounds are either with the "common name" after the
International Organization for Standardization (ISO) oder mit dem chemischen Namen oder mit der Codenummer bezeichnet) und umfassen stets sämtliche International Organization for Standardization (ISO) or with the chemical name or code number) and always include all
Anwendungsformen wie Säuren, Salze, Ester und Isomere wie Stereoisomere und optische Isomere. Dabei sind beispielhaft eine und zum Teil auch mehrere Use forms such as acids, salts, esters and isomers such as stereoisomers and optical isomers. Here are one example and some also several
Anwendungsformen genannt: Rhizobitoxin, 2-Amino-ethoxy-vinylglycin (AVG), Methoxyvinylglycin (MVG), Application forms called: rhizobitoxin, 2-amino-ethoxy-vinylglycine (AVG), methoxyvinylglycine (MVG),
Vinylglycin, Aminooxyessigsäure, Sinefungin, S-Adenosylhomocystein, 2-Keto-4- Methylthiobutyrat, (lsopropyliden)-aminooxyessigsäure-2-(methoxy)-2-oxoethylester, (lsopropyliden)-aminooxyessigsäure-2-(hexyloxy)-2-oxoethylester, (Cyclohexylidene)- aminooxyessigsäure-2-(isopropyloxy)-2-oxoethylester, Putrescin, Spermidin, Spermin, 1 .8-Diamino-4-aminoethyloctan, L-Canalin, Daminozid, 1 -Aminocyclopropyl-1 - carbonsäure-methylester, N-Methyl-1 -aminocyclopropyl-1 -carbonsäure, 1- Aminocyclopropyl-1 -carbonsäureamid, Substituierte 1 -Aminocyclopropyl-1 - carbonsäurederivate wie sie in DE3335514, EP30287, DE2906507 oder US5123951 beschrieben werden, 1 -Aminocyclopropyl-1 -hydroxamsäure, 1 -Methylcyclopropen, 3- Methylcyclopropen, 1 -Ethylcyclopropen, 1 -n-Propylcyclopropen, 1-Cyclopropenyl- Vinyl glycine, aminooxyacetic acid, sinefungin, S-adenosyl homocysteine, 2-keto-4-methylthiobutyrate, (isopropylidene) aminooxyacetic acid 2- (methoxy) -2-oxoethyl ester, (isopropylidene) aminooxyacetic acid 2- (hexyloxy) -2-oxoethyl ester, (Cyclohexylidenes) - aminooxyacetic acid 2- (isopropyloxy) -2-oxoethyl ester, putrescine, spermidine, spermine, 1 -8-diamino-4-aminoethyloctane, L-canaline, daminozide, 1-aminocyclopropyl-1-carboxylic acid methyl ester, N- Methyl-1-aminocyclopropyl-1-carboxylic acid, 1-aminocyclopropyl-1-carboxamide, substituted 1-aminocyclopropyl-1-carboxylic acid derivatives as described in DE3335514, EP30287, DE2906507 or US5123951, 1-aminocyclopropyl-1-hydroxamic acid, 1-methylcyclopropene , 3-methylcyclopropene, 1-ethylcyclopropene, 1 -n-propylcyclopropene, 1-cyclopropenyl-
Methanol, Carvon, Eugenol, Natriumcycloprop-1 -en-1 -ylacetat, Natriumcycloprop-2-en- 1 -ylacetat, Natrium-3-(cycloprop-2-en-1 -yl)propanoat, Natrium-3-(cycloprop-1-en-1- yl)propanoat, Jasmonsäure, Jasmonsäuremethylester, Jasmonsäureethylester.
Pflanzengesundheit und Keimung beeinflussende Stoffe: Methanol, carvone, eugenol, sodium cycloprop-1 -ene-1-ylacetate, sodium cycloprop-2-ene-1-ylacetate, sodium 3- (cycloprop-2-en-1-yl) propanoate, sodium 3- (cyclopropyl) 1-en-1-yl) propanoate, jasmonic acid, methyl jasmonate, jasmonate. Plant health and germination affecting substances:
Als Kombinationspartner für die Verbindungen der allgemeinen Formel (I) in As a combination partner for the compounds of general formula (I) in
Mischungsformulierungen oder im Tank-Mix sind beispielsweise bekannte Wirkstoffe, die die Pflanzengesundheit beeinflussen, einsetzbar (die Verbindungen sind entweder mit dem "common name" nach der International Organization for Standardization (ISO) oder mit dem chemischen Namen oder mit der Codenummer bezeichnet und umfassen stets sämtliche Anwendungsformen wie Säuren, Salze, Ester und Isomere wie Stereoisomere und optische Isomere): Sarcosin, Phenylalanin, Tryptophan, N'- Methyl-1-phenyl-1 -N,N-diethylaminomethanesulfonamid, Apio-galacturonane wie sie in WO2010017956 beschrieben werden, 4-Oxo-4-[(2-phenylethyl)amino]butansäure, 4- {[2-(1 H-lndol-3-yl)ethyl]amino}-4-oxobutansäure, 4-[(3-Methylpyridin-2-yl)amino]-4- oxobutansäure, Allantoin, 5-Aminolevulinsäure, (2S.3R)-2-(3,4-Dihydroxyphenyl)-3,4- dihydro-2H-chromen-3,5.7-triol und strukturell verwandte Catechine wie sie in Mixture formulations or in the tank mix, for example, known active ingredients that affect plant health, can be used (the compounds are either with the "common name" according to the International Organization for Standardization (ISO) or with the chemical name or with the code number designated and always include all forms of use, such as acids, salts, esters and isomers, such as stereoisomers and optical isomers): sarcosine, phenylalanine, tryptophan, N'-methyl-1-phenyl-1-N, N-diethylaminomethanesulfonamide, apio-galacturonans as described in WO2010017956, 4-Oxo-4 - [(2-phenylethyl) amino] butanoic acid, 4- {[2- (1H-indol-3-yl) ethyl] amino} -4-oxobutanoic acid, 4 - [(3-methylpyridine-2 -yl) amino] -4-oxobutanoic acid, allantoin, 5-aminolevulinic acid, (2S.3R) -2- (3,4-dihydroxyphenyl) -3,4-dihydro-2H-chromen-3,5,7-triol and structurally related Catechins like them in
WO2010122956 beschrieben werden, 2-Hydroxy-4-(methylsulfanyl)butansäure,WO2010122956, 2-hydroxy-4- (methylsulfanyl) butanoic acid,
(3E,3aR,8ßS)-3-({[(2R)-4-Methyl-5-oxo-2,5-dihydrofuran-2-yl]oxy}methylen)-3,3a,4,8ß- tetrahydro-2H-indeno[1 ,2-b]furan-2-on und analoge Lactone wie sie in EP2248421 beschrieben werden, Abscisinsäure, (2Z.4E)-5-[6-Ethinyl-1 -hydroxy-2,6-dimethyl-4- oxocyclohex-2-en-1 -yl]-3-methylpenta-2,4-diensäure, Methyl-(2Z.4E)-5-[6-ethinyl-1- hydroxy-2,6-dimethyl-4-oxocyclohex-2-en-1 -yl]-3-methylpenta-2,4-dienoat, 4- Phenylbuttersäure, Natrium-4-phenylbutanoat, Kalium-4-phenylbutanoat. (3E, 3aR, 8βS) -3 - ({[(2R) -4-methyl-5-oxo-2,5-dihydrofuran-2-yl] oxy} methylene) -3,3a, 4,8β-tetrahydro- 2H-indeno [1,2-b] furan-2-one and analogous lactones as described in EP2248421, abscisic acid, (2Z.4E) -5- [6-ethynyl-1-hydroxy-2,6-dimethyl- 4-oxocyclohex-2-en-1-yl] -3-methylpenta-2,4-dienoic acid, methyl (2Z.4E) -5- [6-ethynyl-1-hydroxy-2,6-dimethyl-4- oxocyclohex-2-en-1-yl] -3-methylpenta-2,4-dienoate, 4-phenylbutyric acid, sodium 4-phenylbutanoate, potassium 4-phenylbutanoate.
Herbizide oder Pflanzenwachstumsregulatoren: Als Kombinationspartner für die Verbindungen der allgemeinen Formel (I) in Herbicides or plant growth regulators: As combination partner for the compounds of the general formula (I) in
Mischungsformulierungen oder im Tank-Mix sind beispielsweise bekannte Wirkstoffe, die auf einer Inhibition von beispielsweise Acetolactat-Synthase, Acetyl-CoA- Carboxylase, Cellulose-Synthase, Enolpyruvylshikimat-3-phosphat-Synthase, Mixture formulations or in the tank mix are, for example, known active substances which are based on an inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase,
Glutamin-Synthetase, p-Hydroxyphenylpyruvat-Dioxygenase, Phytoendesaturase, Photosystem I, Photosystem II, Protoporphyrinogen-Oxidase beruhen, einsetzbar, wie sie z.B. aus Weed Research 26 (1986) 441 -445 oder "The Pesticide Manual", 14th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2006 sowie der entsprechenden 15ten Ausgabe und dort zitierter Literatur beschrieben sind.
Als bekannte Herbizide oder Pflanzenwachstumsregulatoren, die mit Verbindungen der allgemeinen Formel (I) kombiniert werden können, sind z.B. folgende Wirkstoffe zu nennen (die Verbindungen sind entweder mit dem "common name" nach der Glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II, protoporphyrinogen oxidase, can be used, as described, for example, in Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 14th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2006 and the corresponding 15th edition and literature cited therein. As known herbicides or plant growth regulators which can be combined with compounds of the general formula (I), for example, the following active ingredients may be mentioned (the compounds are either with the "common name" according to the
International Organization for Standardization (ISO) oder mit dem chemischen Namen oder mit der Codenummer bezeichnet) und umfassen stets sämtliche International Organization for Standardization (ISO) or with the chemical name or code number) and always include all
Anwendungsformen wie Säuren, Salze, Ester und Isomere wie Stereoisomere und optische Isomere. Dabei sind beispielhaft eine und zum Teil auch mehrere Use forms such as acids, salts, esters and isomers such as stereoisomers and optical isomers. Here are one example and some also several
Anwendungsformen genannt: Application forms called:
Acetochlor, Acibenzolar, Acibenzolar-S-methyl, Acifluorfen, Acifluorfen-sodium, Aclonifen, Alachlor, Allidochlor, Alloxydim, Alloxydim-sodium, Ametryn, Amicarbazone, Amidochlor, Amidosulfuron, Aminocyclopyrachlor, Aminopyralid, Amitrole, Acetochlor, acibenzolar, acibenzolar-S-methyl, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryn, amicarbazone, amidochlor, amidosulfuron, aminocyclopyrachlor, aminopyralid, amitrole,
Ammoniumsulfamat, Ancymidol, Anilofos, Asulam, Atrazine, Azafenidin, Azimsulfuron, Aziprotryn, Beflubutamid, Benazolin, Benazolin-ethyl, Bencarbazone, Benfluralin,Ammonium sulfamate, ancymidol, anilofos, asulam, atrazines, azafenidine, azimsulfuron, aziprotryn, beflubutamide, benazoline, benazolin-ethyl, bencarbazone, benfluralin,
Benfuresate, Bensulide, Bensulfuron, Bensulfuron-methyl, Bentazone, Benzfendizone, Benzobicyclon, Benzofenap, Benzofluor, Benzoylprop, Bicyclopyrone, Bifenox, Bilanafos, Bilanafos-natrium, Bispyribac, Bispyribac-natrium, Bromacil, Bromobutide, Bromofenoxim, Bromoxynil, Bromuron, Buminafos, Busoxinone, Butachlor, Benfuresate, Bensulide, Bensulfuron, Bensulfuron-methyl, Bentazone, Benzofendizone, Benzobicyclone, Benzofenap, Benzofluor, Benzoylprop, Bicyclopyrone, Bifenox, Bilanafos, Bilanafos sodium, Bispyribac, Bispyribac sodium, Bromacil, Bromobutide, Bromofenoxime, Bromoxynil, Bromuron, Buminafos, Busoxinone, Butachlor,
Butafenacil, Butamifos, Butenachlor, Butralin, Butroxydim, Butylate, Cafenstrole, Carbetamide, Carfentrazone, Carfentrazone-ethyl, Chlomethoxyfen, Chloramben, Chlorazifop, Chlorazifop-butyl, Chlorbromuron, Chlorbufam, Chlorfenac, Chlorfenac- natrium, Chlorfenprop, Chlorflurenol, Chlorflurenol-methyl, Chloridazon, Chlorimuron, Chlorimuron-ethyl, Chlormequat-chlorid, Chlornitrofen, Chlorophthalim, Chlorthal- dimethyl, Chlorotoluron, Chlorsulfuron, Cinidon, Cinidon-ethyl, Cinmethylin, Butafenacil, butamifos, butenachlor, butraline, butroxydim, butylates, cafenstroles, carbetamides, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, chloramben, chloroazifop, chlorazifop-butyl, chlorobromuron, chlorobufam, chlorfenac, chlorfenacsodium, chlorfenprop, chlorflurenol, chlorflurenol-methyl, Chloridazon, chlorimuron, chlorimuron-ethyl, chlormequat chloride, chloronitrofen, chlorophthalim, chlorothal-dimethyl, chlorotoluron, chlorosulfuron, cinidone, cinidon-ethyl, cinmethylin,
Cinosulfuron, Clethodim, Clodinafop, Clodinafop-propargyl, Clofencet, Clomazone, Clomeprop, Cloprop, Clopyralid, Cloransulam, Cloransulam-methyl, Cumyluron, Cyanamide, Cyanazine, Cyclanilide, Cycloate, Cyclosulfamuron, Cycloxydim, Cinosulfuron, clethodim, clodinafop, clodinafop-propargyl, clofencet, clomazone, clomeprop, cloprop, clopyralid, cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cyclanilide, cycloate, cyclosulfamuron, cycloxydim,
Cycluron, Cyhalofop, Cyhalofop-butyl, Cyperquat, Cyprazine, Cyprazole, 2,4-D, 2,4- DB, Daimuron/Dymron, Dalapon, Daminozid, Dazomet, n-Decanol, Desmedipham, Desmetryn, Detosyl-Pyrazolate (DTP), Diallate, Dicamba, Dichlobenil, Dichlorprop, Dichlorprop-P, Diclofop, Diclofop-methyl, Diclofop-P-methyl, Diclosulam, Diethatyl, Diethatyl-ethyl, Difenoxuron, Difenzoquat, Diflufenican, Diflufenzopyr, Diflufenzopyr- natrium, Dimefuron, Dikegulac-sodium, Dimefuron, Dimepiperate, Dimethachlor,
Dimethametryn, Dimethenamid, Dimethenamid-P, Dimethipin, Dimetrasulfuron, Dinitramine, Dinoseb, Dinoterb, Diphenamid, Dipropetryn, Diquat, Diquat-dibromide, Dithiopyr, Diuron, DNOC, Eglinazine-ethyl, Endothal, EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron, Ethametsulfuron-methyl, Ethephon, Ethidimuron, Ethiozin, Cycluron, Cyhalofop, Cyhalofop-butyl, Cyperquat, Cyprazine, Cyprazole, 2,4-D, 2,4-DB, Daimurone / Dymron, Dalapon, Daminozide, Dazomet, n-Decanol, Desmedipham, Desmetryn, Detosyl-Pyrazolate (DTP) , Dialkylates, dicamba, dichlobenil, dichlorprop, dichlorprop-P, diclofop, diclofop-methyl, diclofop-P-methyl, diclosulam, diethatyl, diethyl-ethyl, difenoxuron, difenzoquat, diflufenican, difluufenzopyr, difluoropentyrimidate, dimefuron, dikegulac-sodium , Dimefuron, dimepiperate, dimethachlor, Dimethyamine, dimethenamid, dimethenamid-P, dimethipine, dimetrasulfuron, dinitramine, dinoseb, dinoterb, diphenamid, dipropetryn, diquat, diquat-dibromide, dithiopyr, diuron, DNOC, eglinazine-ethyl, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron, ethametsulfuron methyl, ethephon, ethidimuron, ethiozine,
Ethofumesate, Ethoxyfen, Ethoxyfen-ethyl, Ethoxysulfuron, Etobenzanid, F-5331 , d.h. N-[2-Chlor-4-fluor-5-[4-(3-fluorpropyl)-4-5-dihydro-5-oxo-1 H-tetrazol-1-yl]-phenyl]- ethansulfonamid, F-7967, d. h. 3-[7-Chlor-5-fiuor-2-(trifluormethyl)-1 H-benzimidazol-4- yl]-1 -methyl-6-(trifluormethyl)pyrimidin-2,4(1 H,3H)-dion, Fenoprop, Fenoxaprop, Fenoxaprop-P, Fenoxaprop-ethyl, Fenoxaprop-P-ethyl, Fenoxasulfone, Fentrazamide, Fenuron, Flamprop, Flamprop-M-isopropyl, Flamprop-M-methyl, Flazasulfuron, Florasulam, Fluazifop, Fluazifop-P, Fluazifop-butyl, Fluazifop-P-butyl, Fluazolate, Flucarbazone, Flucarbazone-sodium, Flucetosulfuron, Fluchloralin, Flufenacet (Thiafluamide), Flufenpyr, Flufenpyr-ethyl, Flumetralin, Flumetsulam, Flumiclorac, Flumiclorac-pentyl, Flumioxazin, Flumipropyn, Fluometuron, Fluorodifen, Ethofumesate, ethoxyfen, ethoxyfen-ethyl, ethoxysulfuron, etobenzanide, F-5331, i. N- [2-chloro-4-fluoro-5- [4- (3-fluoropropyl) -4-5-dihydro-5-oxo-1H-tetrazol-1-yl] -phenyl] -ethanesulfonamide, F-7967 , d. H. 3- [7-chloro-5-fluoro-2- (trifluoromethyl) -1H-benzimidazol-4-yl] -1-methyl-6- (trifluoromethyl) pyrimidine-2,4 (1H, 3H) -dione, Fenoprop, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fentrazamide, fenuron, flamprop, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop, fluazifop-P, fluazifop butyl, fluazifop-p-butyl, fluazolates, flucarbazones, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet (thiafluamide), flufenpyr, flufenpyr-ethyl, flumetralin, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazine, flumipropyn, fluometuron, fluorodifen,
Fluoroglycofen, Fluoroglycofen-ethyl, Flupoxam, Flupropacil, Flupropanate, Fluoroglycofen, fluoroglycofen-ethyl, flupoxam, flupropacil, flupropanate,
Flupyrsulfuron, Flupyrsulfuron-methyl-sodium, Flurenol, Flurenol-butyl, Fluridone, Flurochloridone, Fluroxypyr, Fluroxypyr-meptyl, Flurprimidol, Flurtamone, Fluthiacet, Fluthiacet-methyl, Fluthiamide, Fomesafen, Foramsulfuron, Forchlorfenuron, Flupyrsulfuron, Flupyrsulfuron-methyl-sodium, Flurenol, Flurenol-butyl, Fluridone, Flurochloridone, Fluroxypyr, Fluroxypyr-meptyl, Flurprimidol, Flurtamone, Fluthiacet, Fluthiacet-methyl, Fluthiamide, Fomesafen, Foramsulfuron, Forchlorfenuron,
Fosamine, Furyloxyfen, Gibberellinsäure, Glufosinate, Glufosinate-ammonium, Glufosinate-P, Glufosinate-P-ammonium, Glufosinate-P-natrium, Glyphosate, Fosamines, furyloxyfen, gibberellic acid, glufosinate, glufosinate-ammonium, glufosinate-P, glufosinate-P-ammonium, glufosinate-P-sodium, glyphosate,
Glyphosate-isopropylammonium, H-9201 , d. h. 0-(2,4-Dimethyl-6-nitrophenyl)-0-ethyl- isopropylphosphoramidothioat, Halosafen, Halosulfuron, Halosulfuron-methyl, Glyphosate isopropylammonium, H-9201, d. H. 0- (2,4-dimethyl-6-nitrophenyl) -0-ethyl-isopropylphosphoramidothioate, halosafen, halosulfuron, halosulfuron-methyl,
Haloxyfop, Haloxyfop-P, Haloxyfop-ethoxyethyl, Haloxyfop-P-ethoxyethyl, Haloxyfop- methyl, Haloxyfop-P-methyl, Hexazinone, HW-02, d. h. 1 -(Dimethoxyphosphoryl)- ethyl(2.4-dichlorphenoxy)acetat, Imazamethabenz, Imazamethabenz-methyl, Haloxyfop, Haloxyfop-P, Haloxyfopethoxyethyl, Haloxyfop-P-ethoxyethyl, Haloxyfop- methyl, Haloxyfop-P-methyl, Hexazinone, HW-02, d. H. 1- (dimethoxyphosphoryl) ethyl (2,4-dichlorophenoxy) acetate, imazamethabenz, imazamethabenz-methyl,
Imazamox, Imazamox-ammonium, Imazapic, Imazapyr, Imazapyr- isopropylammonium, Imazaquin, Imazaquin-ammonium, Imazethapyr, Imazethapyr- ammonium, Imazosulfuron, Inabenfide, Indanofan, Indaziflam, Indolessigsäure (IAA), 4-lndol-3-ylbuttersäure (IBA), lodosulfuron, lodosulfuron-methyl-natrium, loxynil, Ipfencarbazone, Isocarbamid, Isopropalin, Isoproturon, Isouron, Isoxaben, Imazamox, imazamox-ammonium, imazapic, imazapyr, imazapyrisopropylammonium, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyrammonium, imazosulfuron, inabenfide, indanofan, indaziflam, indoleacetic acid (IAA), 4-indol-3-yl-butyric acid (IBA), iodosulfuron, iodosulfuron-methyl-sodium, loxynil, isoparbazone, isocarbamide, isopropalin, isoproturon, isourone, isoxaben,
Isoxachlortole, Isoxaflutole, Isoxapyrifop, KUH-043, d. h. 3-({[5-(Difluormethyl)-1 - methyl-3-(trifluormethyl)-1 H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1 ,2- oxazol, Karbutilate, Ketospiradox, Lactofen, Lenacil, Linuron, Maleinsäurehydrazid, CPA, MCPB, MCPB-methyl, -ethyl und -natrium, ecoprop, Mecoprop-natrium,
Mecoprop-butotyl, Mecoprop-P-butotyl, Mecoprop-P-dimethylammonium, Mecoprop-P- 2-ethylhexyl, Mecoprop-P-kalium, Mefenacet, Mefluidide, Mepiquat-chlorid, Isoxachlortole, isoxaflutole, isoxapyrifop, KUH-043, ie 3 - ({[5- (difluoromethyl) -1-methyl-3- (trifluoromethyl) -1H-pyrazol-4-yl] methyl} sulfonyl) -5,5- dimethyl-4,5-dihydro-1, 2-oxazole, carbutilates, ketospiradox, lactofen, lenacil, linuron, maleic hydrazide, CPA, MCPB, MCPB-methyl, -ethyl and -sodium, ecoprop, mecoprop-sodium, Mecopropbutotyl, mecoprop-p-butotyl, mecoprop-P-dimethylammonium, mecoprop-P-2-ethylhexyl, mecoprop-P-potassium, mefenacet, mefluidides, mepiquat chloride,
Mesosulfuron, Mesosulfuron-methyl, Mesotrione, Methabenzthiazuron, Metam, Metamifop, Metamitron, Metazachlor, Metazasulfuron, Methazole, Methiopyrsulfuron, Methiozolin, Methoxyphenone, Methyldymron, 1 -Methylcyclopropen, Mesosulfuron, mesosulfuron-methyl, mesotrione, methabenzthiazuron, metam, metamifop, metamitron, metazachlor, metazasulfuron, methazoles, methiopyrsulfuron, methiozoline, methoxyphenones, methyldymron, 1-methylcyclopropene,
Methylisothiocyanat, Metobenzuron, Metobromuron, Metolachlor, S-Metolachlor, Metosulam, Metoxuron, Metribuzin, Metsulfuron, Metsulfuron-methyl, Molinate, Monalide, Monocarbamide, Monocarbamide-dihydrogensulfat, Monolinuron, Methyl isothiocyanate, metobenzuron, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinates, monalides, monocarbamides, monocarbamide dihydrogen sulfate, monolinuron,
Monosulfuron, Monosulfuron-ester, Monuron, MT-128, d. h. 6-Chlor-N-[(2E)-3- chlorprop-2-en-1-yl]-5-methyl-N-phenylpyridazin-3-amin, MT-5950, d. h. N-[3-Chlor-4- (1 -methylethyl)-phenyl]-2-methylpentanamid, NGGC-01 1 , Naproanilide, Napropamide, Naptalam, NC-310, d.h. 4-(2,4-Dichlorobenzoyl)-1 -methyl-5-benzyloxypyrazole, Neburon, Nicosulfuron, Nipyraclofen, Nitralin, Nitrofen, Nitrophenolat-natrium Monosulfuron, Monosulfuron Ester, Monuron, MT-128, d. H. 6-Chloro-N - [(2E) -3-chloroprop-2-en-1-yl] -5-methyl-N-phenylpyridazine-3-amine, MT-5950, d. H. N- [3-chloro-4- (1-methylethyl) phenyl] -2-methylpentanamide, NGGC-01 1, naproanilides, napropamide, naptalam, NC-310, i. 4- (2,4-Dichlorobenzoyl) -1-methyl-5-benzyloxypyrazoles, neburone, nicosulfuron, nipyraclofen, nitrite, nitrofen, nitrophenolate sodium
(Isomerengemisch), Nitrofluorfen, Nonansäure, Norflurazon, Orbencarb, (Mixture of isomers), nitrofluorfen, nonanoic acid, norflurazon, orbencarb,
Orthosulfamuron, Oryzalin, Oxadiargyl, Oxadiazon, Oxasulfuron, Oxaziclomefone, Oxyfluorfen, Paclobutrazol, Paraquat, Paraquat-dichlorid, Pelargonsäure Orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paclobutrazole, paraquat, paraquat-dichloride, pelargonic acid
(Nonansäure), Pendimethalin, Pendralin, Penoxsulam, Pentanochlor, Pentoxazone, Perfluidone, Pethoxamid, Phenisopham, Phenmedipham, Phenmedipham-ethyl, Picloram, Picolinafen, Pinoxaden, Piperophos, Pirifenop, Pirifenop-butyl, Pretilachlor, Primisulfuron, Primisulfuron-methyl, Probenazole, Profluazol, Procyazine, Prodiamine, Prifluraline, Profoxydim, Prohexadione, Prohexadione-calcium, Prohydrojasmone, Prometon, Prometryn, Propachlor, Propanil, Propaquizafop, Propazine, Propham, Propisochlor, Propoxycarbazone, Propoxycarbazone-natrium, Propyrisulfuron, (Nonanoic acid), pendimethalin, pendalkin, penoxsulam, pentanochlor, pentoxazone, perfluidone, pethoxamide, phenisopham, phenmedipham, phenmediphamethyl, picloram, picolinafen, pinoxaden, piperophos, pirifenop, pirifenoputyl, pretilachlor, primisulfuron, primisulfuron-methyl, probenazoles, Profluazole, Procyazine, Prodiamine, Prifluralin, Profoxydim, Prohexadione, Prohexadione-calcium, Prohydrojasmone, Prometon, Prometry, Propachlor, Propanil, Propaquizafop, Propazine, Propam, Propisochlor, Propoxycarbazone, Propoxycarbazone-Sodium, Propyrisulfuron,
Propyzamide, Prosulfaiin, Prosulfocarb, Prosulfuron, Prynachlor, Pyraclonil, Pyraflufen, Pyraflufen-ethyl, Pyrasulfotole, Pyrazolynate (Pyrazolate), Pyrazosulfuron, Propyzamide, Prosulfaiin, Prosulfocarb, Prosulfuron, Prynachlor, Pyraclonil, Pyraflufen, Pyraflufen-ethyl, Pyrasulfotole, Pyrazolynate (Pyrazolate), Pyrazosulfuron,
Pyrazosulfuron-ethyl, Pyrazoxyfen, Pyribambenz, Pyribambenz-isopropyl, Pyrazosulfuron-ethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl,
Pyribambenz-propyl, Pyribenzoxim, Pyributicarb, Pyridafol, Pyridate, Pyriftalid, Pyribambenz-propyl, Pyribenzoxime, Pyributicarb, Pyridafol, Pyridate, Pyriftalid,
Pyriminobac, Pyriminobac-methyl, Pyrimisulfan, Pyrithiobac, Pyrithiobac-natrium, Pyroxasulfone, Pyroxsulam, Quinclorac, Quinmerac, Quinoclamine, Quizalofop, Quizalofop-ethyl, Quizalofop-P, Quizalofop-P-ethyl, Quizalofop-P-tefuryl, Rimsulfuron, Saflufenacil, Secbumeton, Sethoxydim, Siduron, Simazine, Simetryn, SN-106279, d. h. Methyl-(2R)-2-({7-[2-chlor-4-(trifluormethyl)phenoxy]-2-naphthyl}oxy)-propanoat. Pyriminobac, Pyriminobac-methyl, Pyrimisulfan, Pyrithiobac, Pyrithiobac Sodium, Pyroxasulfones, Pyroxsulam, Quinclorac, Quinmerac, Quinoclamine, Quizalofop, Quizalofop-ethyl, Quizalofop-P, Quizalofop-P-ethyl, Quizalofop-P-tefuryl, Rimsulfuron, Saflufenacil, Secbumeton, Sethoxydim, Siduron, Simazine, Simetryn, SN-106279, d. H. Methyl (2R) -2 - ({7- [2-chloro-4- (trifluoromethyl) phenoxy] -2-naphthyl} oxy) propanoate.
Sulcotrione, Sulfallate (CDEC), Sulfentrazone, Sulfometuron, Sulfometuron-methyl, Sulfosate (Giyphosate-trimesium), Sulfosulfuron, SYN-523, SYP-249, d. h. 1-Ethoxy-3-
methyl-1 -oxobut-3-en-2-yl-5-[2-chlor-4-(trifluormethyl)phenoxy]-2-nitrobenzoat, SYP- 300, d. h. 1 -[7-Fluor-3-oxo-4-(prop-2-in-1 -yl)-3,4-dihydro-2H-1 ,4-benzoxazin-6-yl]-3- propyl-2-thioxoimidazolidin-4,5-dion, Tebutam, Tebuthiuron, Tecnazene, Tefuryltrione, Tembotrione, Tepraloxydim, Terbacil, Terbucarb, Terbuchlor, Terbumeton, Sulcotrione, sulfallates (CDEC), sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosate (Giyphosate-trimesium), sulfosulfuron, SYN-523, SYP-249, ie 1-ethoxy-3- Methyl 1-oxobut-3-en-2-yl-5- [2-chloro-4- (trifluoromethyl) phenoxy] -2-nitrobenzoate, SYP-300, ie 1 - [7-fluoro-3-oxo-4 - (prop-2-yn-1-yl) -3,4-dihydro-2H-1,4-benzoxazin-6-yl] -3-propyl-2-thioxoimidazolidine-4,5-dione, tebutam, tebuthiuron, Tecnazene, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbuchlor, terbumeton,
Terbuthylazine, Terbutryn, Thenylchlor, Thiafluamide, Thiazafluron, Thiazopyr, Thidiazimin, Thidiazuron, Thiencarbazone, Thiencarbazone-methyl, Thifensulfuron, Thifensulfuron-methyl, Thiobencarb, Thiocarbazil, Topramezone, Tralkoxydim, Triallate, Triasulfuron, Triaziflam, Triazofenamide, Tribenuron, Tribenuron-methyl, Trichloressigsäure (TCA), Triclopyr, Tridiphane, Trietazine, Trifloxysulfuron, Terbuthylazine, terbutryn, thenylchloro, thiafluamides, thiazafluron, thiazopyr, thidiazimine, thidiazuron, thiencarbazones, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, thiocarbazil, toramezone, tralkoxydim, triallate, triasulfuron, triaziflam, triazofenamide, tribenuron, tribenuron-methyl, Trichloroacetic acid (TCA), triclopyr, tridiphane, trietazine, trifloxysulfuron,
Trifloxysulfuron-natrium, Trifluralin, Triflusulfuron, Triflusulfuron-methyl, Trimeturon, Trinexapac, Trinexapac-ethyl, Tritosulfuron, Tsitodef, Uniconazole, Uniconazole-P, Vernolate, ZJ-0862, d. h. 3,4-Dichlor-N-{2-[(4.6-dimethoxypyrimidin-2- yl)oxy]benzyl}anilin, sowie die folgenden Verbindungen: Trifloxysulfuron Sodium, Trifluralin, Triflusulfuron, Triflusulfuron-methyl, Trimeturon, Trinexapac, Trinexapac-ethyl, Tritosulfuron, Tsitodef, Uniconazole, Uniconazole-P, Vernolate, ZJ-0862, d. H. 3,4-dichloro-N- {2 - [(4.6-dimethoxypyrimidin-2-yl) oxy] benzyl} aniline, and the following compounds:
Die Erfindung soll durch die nachfolgenden biologischen Beispiele veranschaulicht werden, ohne sie jedoch darauf einzuschränken. Biologische Beispiele: The invention will be illustrated by the following biological examples without, however, limiting them thereto. Biological examples:
Samen von mono- bzw. dikotylen Kulturpflanzen wurden in Holzfasertöpfen in sandigem Lehmboden ausgelegt, mit Erde oder Sand abgedeckt und im Gewächshaus unter guten Wachstumsbedingungen angezogen. Die Behandlung der Seeds of monocotyledonous or dicotyledonous crops were placed in sandy loam soil in wood fiber pots, covered with soil or sand, and grown in the greenhouse under good growth conditions. The treatment of
Versuchspflanzen erfolgte im frühen Laubblattstadium (BBCH10 - BBCH13). Zur Gewährleistung einer uniformen Wasserversorgung vor Stressbeginn wurden die
bepflanzten Töpfe vor Substanzapplikation durch Anstaubewässerung mit Wasser versorgt. Die in Form von benetzbaren Pulvern (WP) formulierten erfindungsgemassen Verbindungen wurden als wässrige Suspension mit einer Wasseraufwandmenge von umgerechnet 600 l/ha unter Zusatz von 0,2% Netzmittel (z.B. Agrotin) auf die grünen Pflanzenteile gesprüht. Unmittelbar nach Substanzapplikation erfolgte die Test plants took place in the early leaves leaf stage (BBCH10 - BBCH13). To ensure a uniform water supply before the onset of stress, the planted pots before substance application by dewatering water supplied. The inventive compounds formulated in the form of wettable powders (WP) were sprayed onto the green parts of plants as an aqueous suspension with a water application rate of 600 l / ha with the addition of 0.2% wetting agent (eg agrotin). Immediately after substance administration was the
Stressbehandlung der Pflanzen. Dazu wurden die Töpfe in Plastikeinsätze transferiert, um anschliessendes, zu schnelles Abtrocknen zu verhindern. Der Trockenstress wurde durch langsames Abtrocknen unter folgenden Bedingungen induziert: „Tag": 14 Stunden beleuchtet bei 26°C Stress treatment of the plants. For this purpose, the pots were transferred to plastic inserts in order to prevent subsequent, too rapid drying. Drought stress was induced by slow drying under the following conditions: "day": 14 hours illuminated at 26 ° C
„Nacht": 10 Stunden ohne Beleuchtung bei 18°C. "Night": 10 hours without lighting at 18 ° C.
Die Dauer der jeweiligen Stressphasen richtete sich hauptsächlich nach dem Zustand der unbehandelten, gestressten Kontrollpflanzen und variierte somit von Kultur zu Kultur. Sie wurde (durch Wiederbewässerung und. Transfer in ein Gewächshaus mit guten Wachstumsbedingungen) beendet, sobald irreversible Schäden an den unbehandelten, gestressten Kontrollpflanzen zu beobachten waren. Bei dikotylen Kulturen wie beispielsweise Raps und Soja variierte die Dauer der The duration of the respective stress phases was mainly dependent on the condition of the untreated, stressed control plants and thus varied from culture to culture. It was terminated (by irrigation and transfer to a greenhouse with good growth conditions) as soon as irreversible damage to the untreated, stressed control plants was observed. For dicotyledonous crops such as oilseed rape and soybean, the duration of the diet varied
Trockenstressphase zwischen 3 und 6 Tagen, bei monokotylen Kulturen wie beispielweise Weizen, Gerste oder Mais zwischen 6 und 1 1 Tagen. Drought phase between 3 and 6 days, in monocotyledonous crops such as wheat, barley or corn between 6 and 1 1 days.
Nach Beendigung der Stressphase folgte eine ca. 5-7 tägige Erholungsphase, während der die Pflanzen abermals unter guten Wachstumsbedingungen im After completion of the stress phase followed by a 5-7 day recovery period during which the plants again under good growth conditions in
Gewächshaus gehalten wurden. Greenhouse were kept.
Um auszuschliessen, dass die beobachteten Effekte von der ggf. fungiziden oder Insektiziden Wirkung der Testverbindungen beeinflusst wurden, wurde zudem darauf geachtet, dass die Versuche ohne Pilzinfektion oder Insektenbefall abliefen. Nach Beendigung der Erholungsphase wurden die Schadintensitäten visuell imIn order to rule out that the observed effects were influenced by the possibly fungicidal or insecticidal activity of the test compounds, care was also taken that the experiments proceeded without fungus infection or insect infestation. After completion of the recovery phase, the damage intensities were visually im
Vergleich zu unbehandelten, ungestressten Kontrollen gleichen Alters bonitiert. Die Erfassung der Schadintensität erfolgte zunächst prozentual (100% = Pflanzen sind abgestorben, 0 % = wie Kontrollpflanzen). Aus diesen Werten wurde sodann der
Wirkungsgrad der Testverbindungen (= prozentuale Reduktion der Schadintensität durch Substanzapplikation) nach folgender Formel ermittelt:
Compared to untreated, unstressed controls of the same age. The detection of the damage intensity was initially percentage (100% = plants are dead, 0% = as control plants). From these values was then the Efficiency of the test compounds (= percentage reduction of the damage intensity by substance application) determined according to the following formula:
SW ug SW ug
WG: Wirkungsgrad (%) WG: Efficiency (%)
SWug: Schadwert der unbehandelten, gestressten Kontrolle SWug: Damage value of untreated, stressed control
SWbg: Schadwert der mit Testverbindung behandelten Pflanzen SWbg: Damage of test compound treated plants
In jedem Versuch wurden pro Kultur und Dosierung 3 Töpfe behandelt und In each experiment 3 pots were treated per culture and dosage and
ausgewertet, bei den resultierenden Wirkungsgraden handelte es sich also um evaluated, so the resulting efficiencies were about
Mittelwerte. Die in den unten stehenden Tabellen A-1 bis A-3 angegebenen Werte sind wiederum Mittelwerte aus ein bis drei unabhängigen Versuchen. Averages. The values given in Tables A-1 to A-3 below are again mean values from one to three independent experiments.
Wirkungen ausgewählter Verbindungen der allgemeinen Formel (I) unter Effects of selected compounds of general formula (I) under
Trockenstress: Drought Stress:
Tabelle A-1 Table A-1
Tabelle A-2 Table A-2
Tabelle A-3 Table A-3
In den zuvor genannten Tabellen bedeuten: In the aforementioned tables mean:
BRSNS = Brassica napus BRSNS = Brassica napus
TRZAS = Triticum aestivum TRZAS = Triticum aestivum
ZEAMX = Zea mays ZEAMX = Zea mays
Ähnliche Ergebnisse konnten auch noch mit weiteren Verbindungen der allgemeinen Formel (I) auch bei Applikation auf andere Pflanzenarten erzielt werden.
Similar results could also be achieved with other compounds of general formula (I) even when applied to other plant species.
Claims
Patentansprüche BCS12-1049 Claims BCS12-1049
Verwendung substituierter 1 -(Arylethinyl)-, 1 -(Heteroarylethinyl)-, 1 - (Heterocyclylethinyl)- und 1 -(Cyloalkenylethinyl)-cyclohexanoie der allge Formel (I) oder deren Salze Use of substituted 1 - (arylethynyl) -, 1 - (heteroarylethynyl) -, 1 - (heterocyclylethynyl) - and 1 - (cycloalkenylethynyl) -cyclohexanoie of the general formula (I) or salts thereof
zur Erhöhung der Stresstoleranz in Pflanzen gegenüber abiotischem Stress und/oder zur Erhöhung des Pflanzenertrags, to increase the stress tolerance in plants to abiotic stress and / or to increase plant yield,
wobei in which
[X-Y] für die Gruppierungen [X-Y] for the groupings
[X-Yp [X-Y]2 , E -Y]3 und [x-Y]4 steht, [X-Yp [XY] 2 , E-Y] 3 and [xY] 4 ,
Q für die Gruppierungen Q-1 bis Q-6 Q for the groupings Q-1 to Q-6
Q-1 Q-2 Q-3
Q-1 Q-2 Q-3
steht, wobei R7, R8, R9, R10, R11, R12, R13, R14, R17, R18, R19, R20, R22, R23, R24, R25, R26, R28, R29 und R30 und A1 bis A9 jeweils die Bedeutung gemäß der nachstehenden Definitionen haben und wobei der Pfeil für eine Bindung zur jeweiligen Gruppierung C-R6 in der allgemeinen where R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 17 , R 18 , R 19 , R 20 , R 22 , R 23 , R 24 , R 25 , R 26 , R 28 , R 29 and R 30 and A 1 to A 9 each have the meaning as defined below, and wherein the arrow for a bond to the respective group CR 6 in the general
Formel (I) steht, Formula (I) stands,
R1 für Alkyl, Cycloalkyl, Cycloalkenyl, Alkenyl, Alkinyl, Alkenylalkyl, R 1 is alkyl, cycloalkyl, cycloalkenyl, alkenyl, alkynyl, alkenylalkyl,
Alkinylalkyl, Alkoxyalkyl, Hydroxyalkyl, Haloalkyl, Haloalkenyl, Alkynylalkyl, alkoxyalkyl, hydroxyalkyl, haloalkyl, haloalkenyl,
Haloalkinyl, Haloalkoxyalkyl, Alkoxyhaloalkyl, Haloalkoxyhaloalkyl, Alkylthioalkyl, Haloalkylthioalkyl, Aryl, Heteroaryl, Heterocyclyl steht, Haloalkynyl, haloalkoxyalkyl, alkoxyhaloalkyl, haloalkoxyhaloalkyl, alkylthioalkyl, haloalkylthioalkyl, aryl, heteroaryl, heterocyclyl,
R2, R3 und R4 unabhängig voneinander für Wasserstoff, Halogen, Alkyl, R 2 , R 3 and R 4 independently of one another represent hydrogen, halogen, alkyl,
Cycloalkyl, Cycloalkenyl, Alkenyl, Alkinyl, Alkenylalkyl, Alkinylalkyl, Alkoxyalkyl, Hydroxyalkyl, Haloalkyl, Haloalkenyl, Haloalkinyl, Cycloalkyl, cycloalkenyl, alkenyl, alkynyl, alkenylalkyl, alkynylalkyl, alkoxyalkyl, hydroxyalkyl, haloalkyl, haloalkenyl, haloalkynyl,
Haloalkoxyalkyl, Alkoxyhaloalkyl, Haloalkoxyhaloalkyl, Alkylthioalkyl, Haloalkylthioalkyl, Aryl, Heteroaryl, Heterocyclyl stehen, Haloalkoxyalkyl, alkoxyhaloalkyl, haloalkoxyhaloalkyl, alkylthioalkyl, haloalkylthioalkyl, aryl, heteroaryl, heterocyclyl,
R5 für Hydroxy, Alkoxy, Aryioxy, Cycloalkyloxy, Alkenyioxy, Alkenylalkyloxy, Alkoxyalkyloxy, Alkylcarbonyloxy, Arylcarbonyloxy, R 5 is hydroxy, alkoxy, aryloxy, cycloalkyloxy, alkenyioxy, alkenylalkyloxy, alkoxyalkyloxy, alkylcarbonyloxy, arylcarbonyloxy,
Heteroarylcarbonyloxy, Cycloalkylcarbonyloxy, Alkoxycarbonyloxy, Allyloxycarbonyloxy, Aryloxyalkyloxy, Arylalkyioxy, Alkoxyalkoxyalkyloxy, Alkylthioalkyloxy, Trialkylsilyloxy, Alkyl(Bis-alkyl)silyloxy, Alkyl(Bis- Aryl)silyloxy, Aryl(Bis-alkyl)silyloxy, Cycloalkyl(Bis-alkyl)silyloxy, Halo(Bis- alkyl)silyloxy, Trialkylsilylalkoxyalkyloxy, steht, Heteroarylcarbonyloxy, cycloalkylcarbonyloxy, alkoxycarbonyloxy, allyloxycarbonyloxy, aryloxyalkyloxy, arylalkyioxy, alkoxyalkoxyalkyloxy, alkylthioalkyloxy, trialkylsilyloxy, alkyl (bis-alkyl) silyloxy, alkyl (bis-aryl) silyloxy, aryl (bis-alkyl) silyloxy, cycloalkyl (bis-alkyl) silyloxy, Halo (bis-alkyl) silyloxy, trialkylsilylalkoxyalkyloxy,
R6 für Nitro, Amino, Hydroxy, Hydrothio, Thiocyanato, Isothiocyanato, R 6 is nitro, amino, hydroxy, hydrothio, thiocyanato, isothiocyanato,
Halogen, Alkyl, Cycloalkyl, Alkenyl, Cycloalkenyl, Alkinyl, Arylalkinyl, Trialkylsilylalkinyl, Aryl, Arylalkyl, Arylalkoxy, Heteroaryl, Haloalkyl,
Halocycloalkyl, Haloalkenyl, Alkoxy, Haloalkoxy, Aryloxy, Heteroaryloxy, Cycloalkyloxy, Cycloalkylalkoxy, Alkenyloxy, Alkinylalkyloxy, Halogen, alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, arylalkynyl, trialkylsilylalkynyl, aryl, arylalkyl, arylalkoxy, heteroaryl, haloalkyl, Halocycloalkyl, haloalkenyl, alkoxy, haloalkoxy, aryloxy, heteroaryloxy, cycloalkyloxy, cycloalkylalkoxy, alkenyloxy, alkynylalkyloxy,
Hydroxyalkyl, Alkoxyalkyl, Aryloxyalkyl, Heteroaryloxyalkyl, Alkylthio, Haloalkylthio, Alkoxycarbonylalkylthio, Arylthio, Cycloalkylthio, Hydroxyalkyl, alkoxyalkyl, aryloxyalkyl, heteroaryloxyalkyl, alkylthio, haloalkylthio, alkoxycarbonylalkylthio, arylthio, cycloalkylthio,
Heteroarylthio, Alkylthioalkyl, Alkylamino, Bisalkylamino, Alkenylamino, Cycloalkylamino, Alkylcarbonylamino, Cycloalkylcarbonylamino, Arylcarbonylamino, Heteroarylcarbonylamino, Formylamino, Heteroarylthio, alkylthioalkyl, alkylamino, bisalkylamino, alkenylamino, cycloalkylamino, alkylcarbonylamino, cycloalkylcarbonylamino, arylcarbonylamino, heteroarylcarbonylamino, formylamino,
Haloalkylcarbonylamino, Alkoxycarbonylamino, Haloalkylcarbonylamino, alkoxycarbonylamino,
Alkylaminocarbonylamino, Alkyl(Alkyl-)aminocarbonylamino, Alkylaminocarbonylamino, alkyl (alkyl) aminocarbonylamino,
Alkylsulfonylamino, Cycloalkylsulfonylamino, Arylsulfonylamino, Hetarylsulfonylamino, Sulfonylhaloalkylamino, Aminoalkylsulfonyl, Aminohaloalkylsulfonyl, Alkylaminosulfonyl, Aminosulfonyl, Alkylsulfonylamino, cycloalkylsulfonylamino, arylsulfonylamino, hetarylsulfonylamino, sulfonylhaloalkylamino, aminoalkylsulfonyl, aminohaloalkylsulfonyl, alkylaminosulfonyl, aminosulfonyl,
Bisalkylaminosulfonyl, Cycioalkylaminosulfonyl, Haloalkylaminosulfonyl, Heteroarylaminosulfonyl, Arylaminosulfonyl, Arylalkylaminosulfonyl, Alkylsulfonyl, Cycloalkylsulfonyl, Arylsulfonyl, Alkylsulfinyl, Bisalkylaminosulfonyl, cycloalkylaminosulfonyl, haloalkylaminosulfonyl, heteroarylaminosulfonyl, arylaminosulfonyl, arylalkylaminosulfonyl, alkylsulfonyl, cycloalkylsulfonyl, arylsulfonyl, alkylsulfinyl,
Cycloalkylsulfinyl, Arylsulfinyl, N.S-Dialkylsulfonimidoyl, S- Alkylsulfonimidoyl, Alkylsulfonylaminocarbonyl, Cycloalkylsulfinyl, arylsulfinyl, N.S. dialkylsulfonimidoyl, S-alkylsulfonimidoyl, alkylsulfonylaminocarbonyl,
Cycloalkylsulfonylaminocarbonyl, Arylalkylcarbonylamino, Cycloalkylsulfonylaminocarbonyl, arylalkylcarbonylamino,
Cycloalkylalkylcarbonylamino, Heteroarylcarbonylamino, Cycloalkylalkylcarbonylamino, heteroarylcarbonylamino,
Alkoxyalkylcarbonylamino, Hydroxyalkylcarbonylamino, Alkoxyalkylcarbonylamino, hydroxyalkylcarbonylamino,
Alkoxycarbonylaminoalkylcarbonylamino, Cyano, Cyanoalkyl, Alkoxycarbonylaminoalkylcarbonylamino, cyano, cyanoalkyl,
Hydroxycarbonyl, Alkoxycarbonyl, Cycloalkoxycarbonyl, Hydroxycarbonyl, alkoxycarbonyl, cycloalkoxycarbonyl,
Cycloalkylalkoxycarbonyl, Aryloxycarbonyl, Arylalkoxycarbonyl, Cycloalkylalkoxycarbonyl, aryloxycarbonyl, arylalkoxycarbonyl,
Alkenyloxycarbonyl, Alkinyloxycarbonyl, Haloalkyloxycarbonyl, Alkenyloxycarbonyl, alkynyloxycarbonyl, haloalkyloxycarbonyl,
Alkoxyalkoxycarbonyl, Alkenyloxyalkoxycarbonyl, Alkoxyalkoxycarbonyl, alkenyloxyalkoxycarbonyl,
Alkylaminoalkoxycarbonyl, Trisalkylsilyloxyalkoxycarbonyl, Bis- Alkylaminoalkoxycarbonyl, Alkyl(alkyl)aminoalkoxycarbonyl, Alkylaminoalkoxycarbonyl, trisalkylsilyloxyalkoxycarbonyl, bis-alkylaminoalkoxycarbonyl, alkyl (alkyl) aminoalkoxycarbonyl,
Cyanoalkoxycarbonyl, Heterocyclyl-N-alkoxycarbonyl, Cyanoalkoxycarbonyl, heterocyclyl-N-alkoxycarbonyl,
Heteroaryloxycarbonyl, Heteroarylalkoxycarbonyl, Heteroaryloxycarbonyl, heteroarylalkoxycarbonyl,
Heterocyclylalkoxycarbonyl, Heterocyclyloxycarbonyl, Heterocyclylalkoxycarbonyl, heterocyclyloxycarbonyl,
Alkenylalkoxycarbonyl, Alkinylalkoxycarbonyl, Arylalkinyloxycarbonyl, Arylalkenyloxycarbonyl, Aminocarbonyl, Alkylaminocarbonyl, Alkenylalkoxycarbonyl, alkynylalkoxycarbonyl, arylalkynyloxycarbonyl, arylalkenyloxycarbonyl, aminocarbonyl, alkylaminocarbonyl,
Bisalkylaminocarbonyl, Alkyl(Alkyl)aminocarbonyl, Bisalkylaminocarbonyl, alkyl (alkyl) aminocarbonyl,
Alkyl(Alkoxy)aminocarbonyl, Alkoxyalkylaminocarbonyl,
Alkenylaminocarbonyl, Cycloalkylaminocarbonyl, Arylaminocarbonyl, Arylalkylaminocarbonyl, Heteroarylalkylaminocarbonyl, Alkyl (alkoxy) aminocarbonyl, alkoxyalkylaminocarbonyl, Alkenylaminocarbonyl, cycloalkylaminocarbonyl, arylaminocarbonyl, arylalkylaminocarbonyl, heteroarylalkylaminocarbonyl,
Cyanoalkylaminocarbonyl, Haloalkylaminocarbonyl, Cyanoalkylaminocarbonyl, haloalkylaminocarbonyl,
Alkinylalkylaminocarbonyl, Alkoxycarbonylaminocarbonyl, Alkynylalkylaminocarbonyl, alkoxycarbonylaminocarbonyl,
Arylalkoxycarbonylaminocarbonyl, Hydroxycarbonylalkyl, Arylalkoxycarbonylaminocarbonyl, hydroxycarbonylalkyl,
Alkoxycarbonylalkyl, Cycloalkoxycarbonylalkyl, Alkoxycarbonylalkyl, cycloalkoxycarbonylalkyl,
Cycloalkylalkoxycarbonylalkyl, Alkenyloxycarbonylalkyl, Cycloalkylalkoxycarbonylalkyl, alkenyloxycarbonylalkyl,
Arylalkoxycarbonylalkyl, Alkylaminocarbonylalkyl, Aminocarbonylalkyl, Bisalkylaminocarbonylalkyl, Cycloalkylaminocarbonylalkyl, Arylalkoxycarbonylalkyl, alkylaminocarbonylalkyl, aminocarbonylalkyl, bisalkylaminocarbonylalkyl, cycloalkylaminocarbonylalkyl,
Arylalkylaminocarbonylalkyl, Heteroarylalkylaminocarbonylalkyl, Arylalkylaminocarbonylalkyl, heteroarylalkylaminocarbonylalkyl,
Cyanoalkylaminocarbonylalkyl, Haloalkylaminocarbonylalkyl, Cyanoalkylaminocarbonylalkyl, haloalkylaminocarbonylalkyl,
Alkinylalkylaminocarbonylalkyl, Cycloalkylalkylaminocarbonylalkyl, Alkoxycarbonylaminocarbonylalkyl, Alkynylalkylaminocarbonylalkyl, cycloalkylalkylaminocarbonylalkyl, alkoxycarbonylaminocarbonylalkyl,
Arylalkoxycarbonylaminocarbonylalkyl, Arylalkoxycarbonylaminocarbonylalkyl,
Alkoxycarbonylalkylaminocarbonyl, Hydroxycarbonylalkylaminocarbonyl,Alkoxycarbonylalkylaminocarbonyl, hydroxycarbonylalkylaminocarbonyl,
Arylalkoxycarbonylalkylaminocarbonyl, Alkoxycarbonylheterocyclyl-N- carbonyl, Alkoxycarbonylalkylheterocyclylidenaminocarbonyl, Arylalkoxycarbonylalkylaminocarbonyl, alkoxycarbonylheterocyclyl-N-carbonyl, alkoxycarbonylalkylheterocyclylidenaminocarbonyl,
Alkoxycarbonylheterocyclylidenalkylaminocarbonyl. Alkoxycarbonylheterocyclylidenalkylaminocarbonyl.
Alkoxycarbonylalkyl(alkyl)aminocarbonyl, Alkoxycarbonylalkyl (alkyl) aminocarbonyl,
Alkoxycarbonylcycloalkylidenaminocarbonyl, Heterocyclyl-N-carbonyl,Alkoxycarbonylcycloalkylidene-aminocarbonyl, heterocyclyl-N-carbonyl,
Aminocarbonylalkylaminocarbonyl. Aminocarbonylalkylaminocarbonyl.
Alkylaminocarbonylalkylaminocarbonyl. Alkylaminocarbonylalkylaminocarbonyl.
Cycloalkylaminocarbonylalkylaminocarbonyl. Cycloalkylaminocarbonylalkylaminocarbonyl.
Cycloalkylalkylaminocarbonyl, Cycloalkylalkylaminocarbonylalkyl, Cycloalkylalkylaminocarbonylalkylaminocarbonyl, Cycloalkylalkylaminocarbonyl, cycloalkylalkylaminocarbonylalkyl, cycloalkylalkylaminocarbonylalkylaminocarbonyl,
Alkenylalkylaminocarbonyl, Alkenylaminocarbonylalkyl, Alkenylalkylaminocarbonyl, alkenylaminocarbonylalkyl,
Alkenylalkylaminocarbonylalkyl, Alkylcarbonyl, Cycloalkylcarbonyl, Arylcarbonyl, Formyl, Hydroxyiminomethyl, Aminoiminomethyl, Alkenylalkylaminocarbonylalkyl, alkylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, formyl, hydroxyiminomethyl, aminoiminomethyl,
Alkoxyiminomethyl, Alkylaminoiminomethyl, Dialkylaminoiminomethyl, Cycioalkoxyiminomethyl, Cycloalkylalkoximinomethyl, Aryloximinomethyl,Alkoxyiminomethyl, alkylaminoiminomethyl, dialkylaminoiminomethyl, cycioalkoxyiminomethyl, cycloalkylalkoximinomethyl, aryloximinomethyl,
Arylalkoxyiminomethyl, Arylalkylaminoiminomethyl, Arylalkoxyiminomethyl, arylalkylaminoiminomethyl,
Alkenyloxyiminomethyl, Arylaminoiminomethyl, Alkenyloxyiminomethyl, arylaminoiminomethyl,
Arylsulfonylaminoiminomethyl, Heteroarylalkyl, Heterocyclylalkyl, Hydroxycarbonylheterocyclyl, Alkoxycarbonylheterocyclyl,
Alkenyloxycarbonylheterocyclyl, Alkenylalkoxycarbonylheterocyclyl, Arylalkoxycarbonylheterocyclyl, Cycloalkoxycarbonylheterocyclyl, Cycloalkylalkoxycarbonylheterocyclyl, Aminocarbonylheterocyclyl, Alkylaminocarbonylheterocyclyl, Bis-Alkylaminocarbonylheterocyclyl, Cycloalkylaminocarbonylheterocyclyl, Arylsulfonylaminoiminomethyl, heteroarylalkyl, heterocyclylalkyl, hydroxycarbonylheterocyclyl, alkoxycarbonylheterocyclyl, Alkenyloxycarbonylheterocyclyl, alkenylalkoxycarbonylheterocyclyl, arylalkoxycarbonylheterocyclyl, cycloalkoxycarbonylheterocyclyl, cycloalkylalkoxycarbonylheterocyclyl, aminocarbonylheterocyclyl, alkylaminocarbonylheterocyclyl, bis-alkylaminocarbonylheterocyclyl, cycloalkylaminocarbonylheterocyclyl,
Arylalkylaminocarbonylheterocyclyl, Alkenylaminocarbonylheterocyclyl, Hydroxycarbonylheterocyclylalkyl, Alkoxycarbonylheterocyclylalkyl, Hydroxycarbonylcycloalkylalkyl, Alkoxycarbonylcycloalkylalkyl, Arylalkylaminocarbonylheterocyclyl, alkenylaminocarbonylheterocyclyl, hydroxycarbonylheterocyclylalkyl, alkoxycarbonylheterocyclylalkyl, hydroxycarbonylcycloalkylalkyl, alkoxycarbonylcycloalkylalkyl,
Hydroxyaminocarbonyl, Alkoxyaminocarbonyl, Arylalkoxyaminocarbonyl, Heterocyclyl, Alkylcarbonyioxy, Aryicarbonyioxy, Heteroaryicarbonyloxy, Hydroxyaminocarbonyl, alkoxyaminocarbonyl, arylalkoxyaminocarbonyl, heterocyclyl, alkylcarbonyloxy, aryicarbonyloxy, heteroaryicarbonyloxy,
Cycloalkylcarbonyloxy, Alkoxycarbonyloxy, Alkenyloxycarbonyloxy steht, Cycloalkylcarbonyloxy, alkoxycarbonyloxy, alkenyloxycarbonyloxy,
R7, R8 , R9 und R10 unabhängig voneinander für Wasserstoff, Halogen, Nitro, Amino, Cyano, Alkyl, Aryl, Heteroaryl, Cycioalkyl, Cycloalkenyi, Aikenyl, Alkinyl, Alkenylalkyl, Alkinylalkyl, Hydroxy, Alkoxy, Alkoxyalkoxy,R 7 , R 8 , R 9 and R 10 independently of one another represent hydrogen, halogen, nitro, amino, cyano, alkyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl, acyl, alkynyl, alkenylalkyl, alkynylalkyl, hydroxy, alkoxy, alkoxyalkoxy,
Alkoxyalkyl, Hydroxyalkyl, Haloalkoxy, Haloalkyl, Haloalkenyl, Alkoxyalkyl, hydroxyalkyl, haloalkoxy, haloalkyl, haloalkenyl,
Haloalkinyl, Haloalkoxyalkyl, Alkoxyhaloalkyl, Haloalkoxyhaloalkyl, Hydrothio, Alkylthio, Haloalkylthio, Alkylthioalkyl, Haloalkylthioalkyl, Alkylamino, Bisalkylamino, Alkenylamino, Cycloalkylamino, Haloalkynyl, haloalkoxyalkyl, alkoxyhaloalkyl, haloalkoxyhaloalkyl, hydrothio, alkylthio, haloalkylthio, alkylthioalkyl, haloalkylthioalkyl, alkylamino, bisalkylamino, alkenylamino, cycloalkylamino,
Alkylcarbonylamino, Cycloalkylcarbonylamino, Arylcarbonylamino, Alkylcarbonylamino, cycloalkylcarbonylamino, arylcarbonylamino,
Heteroarylcarbonylamino, Formylamino, Haloalkylcarbonylamino, Alkoxycarbonylamino, Alkylaminocarbonylamino, (Alkyl-)amino- carbonylamino, Alkylsulfonylamino, Cycloalkylsulfonylamino, Heteroarylcarbonylamino, formylamino, haloalkylcarbonylamino, alkoxycarbonylamino, alkylaminocarbonylamino, (alkyl) aminocarbonylamino, alkylsulfonylamino, cycloalkylsulfonylamino,
Arylsulfonylamino, Hetarylsulfonylamino, Sulfonylhaloalkylamino, Aminoalkylsulfonyl, Aminohaloalkylsulfonyl, Alkylaminosulfonyl, Arylsulfonylamino, hetarylsulfonylamino, sulfonylhaloalkylamino, aminoalkylsulfonyl, aminohaloalkylsulfonyl, alkylaminosulfonyl,
Bisalkylaminosulfonyl, Cycloalkylaminosulfonyl, Haloalkylaminosulfonyl, Heteroarylaminosulfonyl, Arylaminosulfonyl, Arylalkylaminosulfonyl, Alkylsulfonyl, Cycloalkylsulfonyl, Arylsulfonyl, Hydroxy carbonyl, Bisalkylaminosulfonyl, cycloalkylaminosulfonyl, haloalkylaminosulfonyl, heteroarylaminosulfonyl, arylaminosulfonyl, arylalkylaminosulfonyl, alkylsulfonyl, cycloalkylsulfonyl, arylsulfonyl, hydroxy carbonyl,
Alkoxycarbonyl, Cycloalkoxycarbonyl, Cycloalkylalkoxycarbonyl, Aryloxycarbonyl, Arylalkoxycarbonyl, Alkenyloxycarbonyl, Alkoxycarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, aryloxycarbonyl, arylalkoxycarbonyl, alkenyloxycarbonyl,
Alkinyloxycarbonyl, Aminocarbonyl, Alkylaminocarbonyl, Alkynyloxycarbonyl, aminocarbonyl, alkylaminocarbonyl,
Bisalkylaminocarbonyl, Alkyl(Alkyl)aminocarbonyl, Bisalkylaminocarbonyl, alkyl (alkyl) aminocarbonyl,
Alkyl(Alkoxy)aminocarbonyl, Alkenylaminocarbonyl,
Cycloalkylaminocarbonyl, Arylaminocarbonyl, Arylalkylaminocarbonyl stehen, Alkyl (alkoxy) aminocarbonyl, alkenylaminocarbonyl, Cycloalkylaminocarbonyl, arylaminocarbonyl, arylalkylaminocarbonyl,
A\ A2, A3 und A4 gleich oder verschieden sind und unabhängig voneinander für N (Stickstoff) oder die Gruppierungen C-H, C-CH3, C-F, C-Cl, C-Br, C-l, C-OCF3, C-OCH3. C-CF3, C-CO2H, C-CO2CH3 stehen, wobei jedoch in keinem Fall mehr als zwei N -Atome benachbart sind, A \ A 2 , A 3 and A 4 are identical or different and represent, independently of one another, N (nitrogen) or the groupings CH, C-CH 3 , CF, C-Cl, C-Br, Cl, C-OCF 3, C- OCH3. C-CF3, C-CO2H, C-CO2CH3, but in no case more than two N atoms are adjacent,
R11 und R12 unabhängig voneinander für Wasserstoff, Halogen, Alkyl, Aryl,R 11 and R 12 independently of one another represent hydrogen, halogen, alkyl, aryl,
Heteroaryi, Heterocyclyl, Cycloaikyl, Alkenyl, Alkinyl, Alkoxy, Alkoxyalkyl, Aryloxyalkyl, Haloalkoxy, Haloalkyl, Haloalkoxyalkyl, Alkoxyhaloalkyl, Haloalkoxyhaloalkyl, Alkylthio, Haloalkylthio, Alkylthioalkyl, Hetaryl
Hydroxycarbonyl, Alkoxycarbonyl, Cycloalkoxycarbonyl, Hydroxycarbonyl, alkoxycarbonyl, cycloalkoxycarbonyl,
Cycloalkylalkoxycarbonyl, Aryloxycarbonyl, Arylalkoxycarbonyl, Cycloalkylalkoxycarbonyl, aryloxycarbonyl, arylalkoxycarbonyl,
Alkenyloxycarbonyl, Alkinyloxycarbonyl, Aminocarbonyl, Alkenyloxycarbonyl, alkynyloxycarbonyl, aminocarbonyl,
Alkylaminocarbonyl, Bisalkylaminocarbonyl, Alkyl(Alkyl)aminocarbonyl, Alkyl(Alkoxy)aminocarbonyl, Alkenylaminocarbonyl, Alkylaminocarbonyl, bisalkylaminocarbonyl, alkyl (alkyl) aminocarbonyl, alkyl (alkoxy) aminocarbonyl, alkenylaminocarbonyl,
Cycloalkylaminocarbonyl, Arylaminocarbonyl, Arylalkylaminocarbonyl, Cycloalkylthio, Heterocyclylthio, Alkylsulfinyl, Arylsulfinyl, Cycloalkylaminocarbonyl, arylaminocarbonyl, arylalkylaminocarbonyl, cycloalkylthio, heterocyclylthio, alkylsulfinyl, arylsulfinyl,
Heteroarylsulfinyl, Cycloalkylsulfinyl, Heterocyclylsulfinyl, Alkylsulfonyl, Aryisuifonyl, Heteroarylsulfonyi, Cycloalkylsulfonyl, Heterocyclyisulfonyl stehen, Heteroarylsulfinyl, cycloalkylsulfinyl, heterocyclylsulfinyl, alkylsulfonyl, arylsulfonyl, heteroarylsulfonyi, cycloalkylsulfonyl, heterocyclyisulfonyl,
A5 für S (Schwefel), O (Sauerstoff) oder die Gruppierungen N-H, N-CH3, N- CH2CH3, N-CH(CH3)2, N-C02t-Bu, N-Aryl, N-Heteroaryl, N-Heterocyclyl steht. A 5 represents S (sulfur), O (oxygen) or the groupings NH, N-CH 3 , N-CH 2 CH 3 , N-CH (CH 3 ) 2, N-CO 2 t-Bu, N-aryl, N-heteroaryl, N-heterocyclyl is.
R13, R14, R17 und R18 unabhängig voneinander für Wasserstoff, Alkyl, Halogen, Cycloaikyl, Aryl, Heteroaryi, Heterocyclyl, Alkenyl, Alkinyl, Alkenylalkyl, Arylalkyl, Alkoxy, Alkoxyalkoxy, Alkoxyalkyl, Hydroxy, Haloalkyl, R 13 , R 14 , R 17 and R 18 are each independently hydrogen, alkyl, halogen, cycloalkyl, aryl, heteroaryl, heterocyclyl, alkenyl, alkynyl, alkenylalkyl, arylalkyl, alkoxy, alkoxyalkoxy, alkoxyalkyl, hydroxy, haloalkyl,
Haloalkylthio, Alkylthio, Arylthio, Cycloalkylthio, Heterocyclylthio, Alkylsulfinyl, Arylsulfinyl, Heteroarylsulfinyl, Cycloalkylsulfinyl, Haloalkylthio, alkylthio, arylthio, cycloalkylthio, heterocyclylthio, alkylsulfinyl, arylsulfinyl, heteroarylsulfinyl, cycloalkylsulfinyl,
Heterocyclylsulfinyl, Alkylsulfonyl, Aryisuifonyl, Heteroarylsulfonyi, Cycloalkylsulfonyl, Heterocyclyisulfonyl stehen oder
R13 und R17 mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls weiter substituierten 5 bis 7-gliedrigen Ring bilden, Heterocyclylsulfinyl, Alkylsulfonyl, Aryisuifonyl, Heteroarylsulfonyi, Cycloalkylsulfonyl, Heterocyclyisulfonyl or R 13 and R 17 with the atoms to which they are attached form a completely saturated or partially saturated, optionally further substituted 5 to 7-membered ring,
A6, A7 gleich oder verschieden sind und unabhängig voneinander für O A 6 , A 7 are the same or different and are each independently O.
(Sauerstoff), S (Schwefel), S=0, S(=0)2, N-H, N+-CH3(-0 ), N-OCH3, N- CH3 oder die Gruppierung CR15R16 stehen, wobei jedoch in keinem Fall zwei O- oder S-Atome benachbart sind, und wobei R15 und R16 in der Gruppierung CR15R16 jeweils gleiche oder verschiedene Bedeutungen gemäß der nachstehenden Definition haben und (Oxygen), S (sulfur), S = O, S (= O) 2 , NH, N + -CH 3 (-O), N-OCH 3 , N-CH 3 or the group CR 15 R 16 , where however, in no case are two O or S atoms adjacent, and wherein R 15 and R 16 in the group CR 15 R 16 each have the same or different meanings as defined below, and
R15 und R16 unabhängig voneinander für Wasserstoff, Halogen, Alkyl, Aryl, Heteroaryl, Heterocyclyl, Cycloalkyl, Alkenyl, Alkoxy, Alkoxyalkyl, Aryloxyalkyl, Haloalkoxy, Haloalkyl, Haloalkoxyalkyl, Alkoxyhaloalkyl, Haloalkoxyhaloalkyl, Alkylthio, Haloalkylthio, Alkylthioalkyl, R 15 and R 16 independently of one another represent hydrogen, halogen, alkyl, aryl, heteroaryl, heterocyclyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl, aryloxyalkyl, haloalkoxy, haloalkyl, haloalkoxyalkyl, alkoxyhaloalkyl, haloalkoxyhaloalkyl, alkylthio, haloalkylthio, alkylthioalkyl,
Hydroxycarbonyl, Alkoxycarbonyl, Cycloalkoxycarbonyl, Hydroxycarbonyl, alkoxycarbonyl, cycloalkoxycarbonyl,
Cycloalkylalkoxycarbonyl, Aryloxycarbonyl, Arylalkoxycarbonyl, Cycloalkylalkoxycarbonyl, aryloxycarbonyl, arylalkoxycarbonyl,
Alkenyloxycarbonyl, Alkinyloxycarbonyl, Aminocarbonyl, Alkenyloxycarbonyl, alkynyloxycarbonyl, aminocarbonyl,
Alkylaminocarbonyl, Bisalkylaminocarbonyl, Alkyl(Alkyl)aminocarbonyl, Alkyl(Alkoxy)aminocarbonyl, Alkenylaminocarbonyl, Alkylaminocarbonyl, bisalkylaminocarbonyl, alkyl (alkyl) aminocarbonyl, alkyl (alkoxy) aminocarbonyl, alkenylaminocarbonyl,
Cycloalkylaminocarbonyl, Arylaminocarbonyl, Arylalkylaminocarbonyl, Amino, Alkylamino, Cycloalkylamino, Bis-Alkylamino, Arylthio, Cycloalkylaminocarbonyl, arylaminocarbonyl, arylalkylaminocarbonyl, amino, alkylamino, cycloalkylamino, bis-alkylamino, arylthio,
Cycloalkylthio, Heterocyclylthio, Alkylsulfinyl, Arylsulfinyl, Cycloalkylthio, heterocyclylthio, alkylsulfinyl, arylsulfinyl,
Heteroarylsulfinyl, Cycloalkylsulfinyl, Heterocyclylsulfinyl, Alkylsulfonyl, Arylsulfonyl, Heteroarylsulfonyl, Cycloalkylsulfonyl, Heterocyclylsulfonyl stehen, Heteroarylsulfinyl, cycloalkylsulfinyl, heterocyclylsulfinyl, alkylsulfonyl, arylsulfonyl, heteroarylsulfonyl, cycloalkylsulfonyl, heterocyclylsulfonyl,
R19, R20, R22 und R23 unabhängig voneinander für Wasserstoff, Alkyl, Halogen, Cycloalkyl, Aryl, Heteroaryl, Heterocyclyl, Alkenyl, Alkinyl, Arylalkyl, Heterocyclylalkyl, Alkoxy, Alkoxyalkoxy, Alkoxyalkyl, Haloalkyl, Alkylthio, Arylthio, Cycloalkylthio, Heterocyclylthio, Alkylsulfinyl, Arylsulfinyl, Heteroarylsulfinyl, Cycloalkylsulfinyl, Heterocyclylsulfinyl, Alkylsulfonyl,
Arylsulfonyl, Heteroarylsulfonyl, Cycloalkylsulfonyl, Heterocyclylsulfonyl stehen, R 19 , R 20 , R 22 and R 23 are each independently hydrogen, alkyl, halogen, cycloalkyl, aryl, heteroaryl, heterocyclyl, alkenyl, alkynyl, arylalkyl, heterocyclylalkyl, alkoxy, alkoxyalkoxy, alkoxyalkyl, haloalkyl, alkylthio, arylthio, cycloalkylthio, Heterocyclylthio, alkylsulfinyl, arylsulfinyl, heteroarylsulfinyl, cycloalkylsulfinyl, heterocyclylsulfinyl, alkylsulfonyl, Arylsulfonyl, heteroarylsulfonyl, cycloalkylsulfonyl, heterocyclylsulfonyl,
A8 für O (Sauerstoff), S (Schwefel), S=0, S(=0)2, N-H, N+-CH3(-G-), N-CH3, N-OCH3 oder die Gruppierung CHR21 steht und wobei R21 in der Gruppierung CHR21 die Bedeutung gemäß der nachstehenden Definition hat. A 8 is O (oxygen), S (sulfur), S = O, S (= O) 2 , NH, N + -CH 3 (-G-), N-CH 3 , N -OCH 3 or the moiety CHR 21 and wherein R 21 in the CHR 21 grouping has the meaning as defined below.
R21 für Wasserstoff, Halogen, Alkyl, Aryl, Heteroaryl, Heterocyclyl, Cycloalkyl, Alkenyl, Alkinyl, Heterocyclylalkyl, Alkoxy, Alkoxyalkyl, Aryloxyalkyl, Haloalkoxy, Haloalkyl, Alkoxyhaloalkyl, Haloalkoxyhaloalkyl, Alkylthio, Haloalkylthio, Alkylthioalkyl, Hydroxycarbonyl, Alkoxycarbonyl, R 21 is hydrogen, halogen, alkyl, aryl, heteroaryl, heterocyclyl, cycloalkyl, alkenyl, alkynyl, heterocyclylalkyl, alkoxy, alkoxyalkyl, aryloxyalkyl, haloalkoxy, haloalkyl, alkoxyhaloalkyl, haloalkoxyhaloalkyl, alkylthio, haloalkylthio, alkylthioalkyl, hydroxycarbonyl, alkoxycarbonyl,
Cycloalkoxycarbonyl, Arylalkoxycarbonyl, Alkenyloxycarbonyl, Cycloalkoxycarbonyl, arylalkoxycarbonyl, alkenyloxycarbonyl,
Alkinyloxycarbonyl, Aminocarbonyl, Alkylaminocarbonyl, Alkynyloxycarbonyl, aminocarbonyl, alkylaminocarbonyl,
Bisalkylaminocarbonyl, Alkyl(Alkyl)aminocarbonyl, Bisalkylaminocarbonyl, alkyl (alkyl) aminocarbonyl,
Alkyl(Alkoxy)aminocarbonyl, Alkenylaminocarbonyl, Alkyl (alkoxy) aminocarbonyl, alkenylaminocarbonyl,
Cycloalkylaminocarbonyl, Arylaminocarbonyl, Arylalkylaminocarbonyl, Amino, Alkylamino, Cycloalkylamino, Bis-Alkylamino, Arylthio, Cycloalkylaminocarbonyl, arylaminocarbonyl, arylalkylaminocarbonyl, amino, alkylamino, cycloalkylamino, bis-alkylamino, arylthio,
Cycloalkylthio, Heterocyclylthio, Alkylsulfinyl, Arylsulfinyl, Cycloalkylthio, heterocyclylthio, alkylsulfinyl, arylsulfinyl,
Heteroarylsulfinyl, Cycloalkylsulfinyl, Heterocyclylsulfinyl, Alkylsulfonyl, Arylsulfonyl, Heteroarylsulfonyl, Cycloalkylsulfonyl, Heterocyclylsulfonyl steht, Heteroarylsulfinyl, cycloalkylsulfinyl, heterocyclylsulfinyl, alkylsulfonyl, arylsulfonyl, heteroarylsulfonyl, cycloalkylsulfonyl, heterocyclylsulfonyl,
R24, R25, R26, R28, R29 und R30 unabhängig voneinander für Wasserstoff, Alkyl, Halogen, Cycloalkyl, Aryl, Heteroaryl, Heterocyclyl, Alkenyl, Alkoxy, Alkoxy alkoxy, Alkoxyalkyl, Haloalkyl, Alkylthio, Haloalkylthio, Arylthio, Cycloalkylthio, Heterocyclylthio, Alkylsulfinyl, Arylsulfinyl, R 24 , R 25 , R 26 , R 28 , R 29 and R 30 are independently hydrogen, alkyl, halogen, cycloalkyl, aryl, heteroaryl, heterocyclyl, alkenyl, alkoxy, alkoxy alkoxy, alkoxyalkyl, haloalkyl, alkylthio, haloalkylthio, arylthio , Cycloalkylthio, heterocyclylthio, alkylsulfinyl, arylsulfinyl,
Heteroarylsulfinyl, Cycloalkylsulfinyl, Heterocyclylsulfinyl, Alkylsulfonyl, Arylsulfonyl, Heteroarylsulfonyl, Cycloalkylsulfonyl, Heterocyclylsulfonyl stehen. Heteroarylsulfinyl, cycloalkylsulfinyl, heterocyclylsulfinyl, alkylsulfonyl, arylsulfonyl, heteroarylsulfonyl, cycloalkylsulfonyl, heterocyclylsulfonyl.
A9 für O (Sauerstoff), S (Schwefel), S=0, S(=0)2, N-H, N+-CH3(-0"), N-CH3, N- OCH3 oder die Gruppierung CHR27 steht und wobei R27 in der
Gruppierung CHR27 die Bedeutung gemäß der nachstehenden Definition hat und A 9 is O (oxygen), S (sulfur), S = O, S (= O) 2 , NH, N + -CH 3 (-O " ), N-CH 3, N -OCH 3 or the moiety CHR 27 and wherein R 27 in the Grouping CHR 27 has the meaning as defined below and
R27 für Wasserstoff, Halogen, Alkyl, Aryl, Heteroaryl, Heterocyclyl, Cycloalkyl, Alkenyl, Alkoxy, Alkoxyalkyl, Aryloxyalkyl, Haloalkoxy, Haloalkyl, Alkylthio, Haloalkylthio, Hydroxycarbonyl, Alkoxycarbonyl, Cycloalkoxycarbonyl, Arylalkoxycarbonyl, Alkenyloxycarbonyl, R 27 is hydrogen, halogen, alkyl, aryl, heteroaryl, heterocyclyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl, aryloxyalkyl, haloalkoxy, haloalkyl, alkylthio, haloalkylthio, hydroxycarbonyl, alkoxycarbonyl, cycloalkoxycarbonyl, arylalkoxycarbonyl, alkenyloxycarbonyl,
Alkinyloxycarbonyl, Aminocarbonyl, Alkylaminocarbonyl, Alkynyloxycarbonyl, aminocarbonyl, alkylaminocarbonyl,
Bisalkylaminocarbonyl, Alkyl(Alkyl)aminocarbonyl, Bisalkylaminocarbonyl, alkyl (alkyl) aminocarbonyl,
Alkyl(Alkoxy)aminocarbonyl, Alkenylaminocarbonyl, Alkyl (alkoxy) aminocarbonyl, alkenylaminocarbonyl,
Cycloalkylaminocarbonyl, Arylaminocarbonyl, Arylalkylaminocarbonyl, Amino, Alkylamino, Cycloalkylamino, Bis-Alkylamino, Arylthio, Cycloalkylaminocarbonyl, arylaminocarbonyl, arylalkylaminocarbonyl, amino, alkylamino, cycloalkylamino, bis-alkylamino, arylthio,
Cycloalkylthio, Heterocyclylthio, Alkylsulfinyl, Arylsulfinyl, Heteroarylsulfinyl, Cycloalkylsulfinyl, Heterocyclylsulfinyl, Alkylsulfonyl, Aryisulfonyl, Heteroarylsulfonyl, Cycloalkylsulfonyl, Heterocyciylsulfonyl steht. Cycloalkylthio, heterocyclylthio, alkylsulfinyl, arylsulfinyl, heteroarylsulfinyl, cycloalkylsulfinyl, heterocyclylsulfinyl, alkylsulfonyl, arylsulfonyl, heteroarylsulfonyl, cycloalkylsulfonyl, heterocyclylsulfonyl.
2. Verwendung gemäß Anspruch 1 , wobei in Formel (I) 2. Use according to claim 1, wherein in formula (I)
[X-Y] für die Gruppierungen [X-Y] for the groupings
[X-Y]1 und [χ-Υ]3 steht, [XY] 1 and [ χ -Υ] 3 ,
Q für die Gruppierungen Q-1 bis Q-6 Q for the groupings Q-1 to Q-6
Q-1 Q-2 Q-3
Q-1 Q-2 Q-3
steht, wobei R7, R8, R9, R10, R11 , R12, R13, R14, R17, R18, R19, R20, R22, R23, R24, R25, R26, R28, R29 und R30 und A1 bis A9 jeweils die Bedeutung gemäß der nachstehenden Definitionen haben und wobei der Pfeil für eine Bindung zur jeweiligen Gruppierung C-R6 in der allgemeinen where R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 17 , R 18 , R 19 , R 20 , R 22 , R 23 , R 24 , R 25 , R 26 , R 28 , R 29 and R 30 and A 1 to A 9 each have the meaning as defined below, and wherein the arrow for a bond to the respective group CR 6 in the general
Formel (I) steht, Formula (I) stands,
R1 für (CrC8)-Alkyl, (C3-C8)-Cycloalkyl, (C4-C8)-Cycloalkenyl, (C2-C8)- Alkenyl, (C2-C8)-Alkinyl, (C2-C8)-Alkenyl-(Ci-C8)-alkyl, (C2-C8)-Alkinyl- (d-C8)-alkyl, (Ci-C8)-Alkoxy-(d-C8)-alkyl, Hydroxy-(Ci-C8)-alkyl, (Ci-Ce)- Haloalkyl, (C2-C8)-Haloalkenyl, (C2-C8)-Haloalkinyl, (Ci-C8)-Haloalkoxy- (Ci-C8)-alkyl, (Ci-C8)-Alkoxy-(Ci-C8)-haloalkyl, (Ci-C8)-Haloalkoxy- (d-C8)-haloalkyl, (Ci-C8)-Alkylthio-(d-C8)-alkyl, (CrCs)-Haloalkylthio- (Ci-Cs)-alkyl, Aryl, Heteroaryl, Heterocyclyl steht, R 1 is (C 1 -C 8 ) -alkyl, (C 3 -C 8 ) -cycloalkyl, (C 4 -C 8 ) -cycloalkenyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl, (C 2 -C 8) alkenyl (Ci-C 8) alkyl, (C 2 -C 8) alkynyl (dC 8) alkyl, (Ci-C 8) alkoxy (dC 8) - alkyl, hydroxy (Ci-C 8) alkyl, (Ci-Ce) - haloalkyl, (C 2 -C 8) -haloalkenyl, (C 2 -C 8) haloalkynyl, (Ci-C8) haloalkoxy (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) -haloalkoxy- (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) - Alkylthio (C 1 -C 8 ) -alkyl, (C 1 -C 5) -haloalkylthio (C 1 -C 8) -alkyl, aryl, heteroaryl, heterocyclyl,
R2, R3 und R4 unabhängig voneinander für Wasserstoff, Halogen, (Ci-C8)-Alkyl, (C3-C8)-Cycloalkyl, (C4-C8)-Cycloalkenyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (C2-C8)-Alkenyl-(CrC8)-alkyl, (C2-C8)-Alkinyl-(d-C8)-alkyl, (Ci-C8)- Alkoxy-(Ci-C8)-alkyl, Hydroxy-(Ci-C8)-alkyl, (d-C8)-Haloalkyl, (C2-C8)- Haloalkenyl, (C2-C8)-Haloalkinyl, (Ci-C8)-Haloalkoxy-(Ci-C8)-alkyl, R 2, R 3 and R 4 are independently hydrogen, halogen, (Ci-C 8) -alkyl, (C 3 -C 8) cycloalkyl, (C 4 -C 8) -cycloalkenyl, (C 2 -C 8 ) alkenyl, (C 2 -C 8) -alkynyl, (C2-C8) alkenyl (-C 8) alkyl, (C 2 -C 8) alkynyl (dC 8) alkyl, (Ci- C 8) - alkoxy (Ci-C 8) alkyl, hydroxy (Ci-C 8) alkyl, (dC 8) -haloalkyl, (C 2 -C 8) - haloalkenyl, (C 2 -C 8) -Haloalkynyl, (C 1 -C 8 ) -haloalkoxy- (C 1 -C 8 ) -alkyl,
(Ci-C8)-Alkoxy-(Ci-C8)-haloalkyl, (Ci-C8)-Haloalkoxy-(Ci-C8)-haloalkyl, (Ci-C8)-Alkylthio-(Ci-C8)-alkyl, (Ci-C8)-Haloalkylthio-(CrC8)-alkyl, Aryl, Heteroaryl, Heterocyclyl stehen, (Ci-C 8) alkoxy (Ci-C 8) haloalkyl, (Ci-C8) haloalkoxy (Ci-C 8) haloalkyl, (Ci-C8) alkylthio (Ci-C 8 ) -alkyl, (C 1 -C 8 ) -haloalkylthio (C 1 -C 8 ) -alkyl, aryl, heteroaryl, heterocyclyl,
R5 für Hydroxy, (d-C8)-Alkoxy, Aryloxy, (C3-C8)-Cycloalkyloxy, (C2-C8)- Alkenyloxy, (C2-C8)-Alkenyl-(d-C8)-alkyloxy, (Ci-C8)-Alkoxy-(Ci-C8)- alkyloxy, (Ci-C8)-Alkylcarbonyloxy, Arylcarbonyloxy, R 5 is hydroxy, (C 1 -C 8 ) alkoxy, aryloxy, (C 3 -C 8 ) cycloalkyloxy, (C 2 -C 8 ) alkenyloxy, (C 2 -C 8 ) alkenyl (C 1 -C 8 ) alkyloxy , (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyloxy, (C 1 -C 8 ) -alkylcarbonyloxy, arylcarbonyloxy,
Heteroarylcarbonyloxy, (C3-C8)-Cycloalkylcarbonyloxy, (d-C8)- Alkoxycarbonyloxy, (C2-C8)-Alkenyloxycarbonyloxy, Aryloxy-(Ci-Cs)-
alkyloxy, Aryl-(Ci-C8)-alkyloxy, (Ci-C8)-Alkoxy-(Ci-C8)-alkoxy-(Ci-C8)- alkyloxy, (Ci-C8)-Alkylthio-(Ci-C8)-alkyloxy, Tris[(CrC8)-alkyl]silyloxy, (Ci-C8)-Alkyl-Bis[(Ci-C8)-alkyl]silyloxy, (Ci-C8)-Alkyl-bis(Aryl)silyloxy, Aryl-bis[(CrC8)— alkyl]silyloxy, Cycloalkyl-bis[(CrC8)-alkyl]silyloxy, Halo- bis[(d-C8)-alkyl]silyloxy, Tris[(Ci-C8)-alkyl]silyl-(Ci-C8)-alkoxy-(CrC8)- alkyloxy, steht, für Nitro, Amino, Hydroxy, Hydrothio, Thiocyanato, Isothiocyanato, Halogen, (Ci-Cs)-Alkyl, (C3-C8)-Cycloalkyl, (C2-C8)-Alkenyl, (C4-Cs)- Cycloalkenyl, (C2-C8)-Alkinyl, Aryl-(C2-Cs)-alkinyl, Tris[(Ci-C8)-alkyl]silyl- (C2-C8)-alkinyl, Aryl, Aryl-(d-C8)-alkyl, Aryl-(Ci-C8)-alkoxy, Heteroaryl, (CrCs)-Haloalkyl, (C3-C8)-Halocycloalkyl, (C2-C8)-Haloalkenyl, (Ci-C8)- Alkoxy, (d-C8)-Haloalkoxy, Aryloxy, Heteroaryloxy, (Ca-Ce)- Cycloalkyloxy, (C3-C8)-Cycloalkyl-(Ci-C8)-alkoxy, (C2-C8)- (C2-C8)- Alkenyloxy, (C2-C8)-Alkinyl-(C2-C8)-alkyloxy, Hydroxy-(d-C8)-alkyl, Heteroarylcarbonyloxy, (C3-C8) cycloalkylcarbonyloxy, (DC 8) - alkoxycarbonyloxy, (C 2 -C 8) -Alkenyloxycarbonyloxy, aryloxy (Ci-Cs) - alkyloxy, aryl- (C 1 -C 8 ) -alkyloxy, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyloxy, (C 1 -C 8 ) -alkylthio (Ci -C 8 ) -alkyloxy, tris [(CrC 8 ) -alkyl] silyloxy, (C 1 -C 8 ) -alkyl-bis [(C 1 -C 8 ) -alkyl] silyloxy, (C 1 -C 8 ) -alkyl-bis (Aryl) silyloxy, aryl bis [(CrC 8 ) alkyl] silyloxy, cycloalkyl bis [(CrC 8 ) alkyl] silyloxy, halo bis [(dC 8 ) alkyl] silyloxy, tris [(Ci-C 8 ) -alkyl] silyl- (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyloxy, for nitro, amino, hydroxy, hydrothio, thiocyanato, isothiocyanato, halogen, (C 1 -C 8) -alkyl, (C 3 -C 8 ) -cycloalkyl, (C 2 -C 8 ) -alkenyl, (C 4 -Cs) -cycloalkenyl, (C 2 -C 8 ) -alkynyl, aryl- (C 2 -Cs) -alkynyl, tris [ (Ci-C 8) alkyl] silyl (C 2 -C 8) alkynyl, aryl, aryl (dC 8) alkyl, aryl (Ci-C 8) alkoxy, heteroaryl, (CRCs) -haloalkyl , (C 3 -C 8) halocycloalkyl, (C 2 -C 8) -haloalkenyl, (Ci-C8) - alkoxy, (dC 8) haloalkoxy, aryloxy, heteroaryloxy, (Ca-Ce) - cycloalkyloxy, ( C 3 -C 8 ) -cycloalkyl- (C 1 -C 8 ) -alkoxy, (C 2 -C 8 ) - (C 2 -C 8 ) -alkenyloxy, (C 2 -C 8 ) -alkynyl- (C 2 -C 8 ) alkyloxy, hydroxy (dC 8 ) alkyl,
(Ci-C8)-Alkoxy-(d-C8)-alkyl, Aryloxy-(d-C8)-alkyl, Heteroaryloxy-(d-C8)- alkyl, (d-C8)-Alkylthio, (d-C8)-Haloalkylthio, (Ci-C8)-Alkoxycarbonyl- (Ci-Cs)-alkylthio, Arylthio, (C3-Ce)-Cycloalkylthio, Heteroarylthio, (Ci-Ce)- Alkylthio-(Ci-C8)-alkyl, (Ci-C8)-Alkylamino, Bis[(Ci-C8)-alkyl]amino, (C2-C8)-Alkenylamino, (C3-C8)-Cycloalkylamino, (Ci-C8)- Alkylcarbonylamino, (C3-C8)-Cycloalkylcarbonylamino, (Ci-C 8) alkoxy (dC 8) alkyl, aryloxy (dC 8) alkyl, heteroaryloxy (dC 8) - alkyl, (DC 8) alkylthio, (DC 8) haloalkylthio, (C -C 8) alkoxycarbonyl (Ci-Cs) alkylthio, arylthio, (C3-Ce) cycloalkylthio, heteroarylthio, (Ci-Ce) - alkylthio (Ci-C8) alkyl, (Ci-C 8) alkylamino, bis [(Ci-C 8) alkyl] amino, (C2 -C8) -alkenylamino, (C3-C8) cycloalkylamino, (Ci-C 8) - alkylcarbonylamino, (C3-C8) -Cycloalkylcarbonylamino,
Arylcarbonylamino, Heteroarylcarbonylamino, Formylamino, (d-C8)- Haloalkylcarbonylamino, (Ci-C8)-Alkoxycarbonylamino, (d-C8)- Alkylaminocarbonylamino, (d-C8)-Alkyl[(Ci-C8)- Alkyl]aminocarbonylamino, (Ci-Cs)-Alkylsulfonylamino, (Ca-C8)- Cycloalkylsulfonylamino, Aryisulfonylamino, Hetarylsulfonylamino, Sulfonyl-(Ci-C8)-haloalkylamino, Amino-(Ci-C8)-alkylsulfonyl, Amino- (Ci-Cs)-haloalkylsulfonyl, (Ci-C8)-Alkylaminosulfonyl, Bis[(Ci-C8)- alkyljaminosulfonyl, (C3-C8)-Cycloaikylaminosulfonyl, (Ci-C8)- Haloalkylaminosulfonyl, Aminosulfonyl, Heteroarylaminosulfonyl, Arylcarbonylamino, heteroarylcarbonylamino, formylamino, (DC 8) - Haloalkylcarbonylamino, (Ci-C8) alkoxycarbonylamino, (DC 8) - alkylaminocarbonylamino, (DC 8) alkyl [(Ci-C 8) - alkyl] aminocarbonylamino, (Ci- Cs) -alkylsulfonylamino, (Ca-C 8 ) -cycloalkylsulfonylamino, arylsulfonylamino, hetarylsulfonylamino, sulfonyl- (C 1 -C 8 ) -haloalkylamino, amino- (C 1 -C 8 ) -alkylsulfonyl, amino- (C 1 -C 8 ) -haloalkylsulfonyl, (Ci-C 8) alkylaminosulfonyl, bis [(Ci-C 8) - alkyljaminosulfonyl, (C3-C8) -Cycloaikylaminosulfonyl, (Ci-C 8) - Haloalkylaminosulfonyl, aminosulfonyl, heteroarylaminosulfonyl,
Arylaminosulfonyl, Aryl-(Ci-C8)-alkylaminosulfonyl, (Ci-C8)-Alkylsulfonyl, (C3-C8)-Cycloalkylsulfonyl, Arylsulfonyl, (Ci-C8)-Alkylsulfinyl, (C3-C8)- Cycioalkylsulfinyl, Arylsulfinyl, N.S-Bis[(Ci-C8)-alkyl]sulfonimidoyl, S- (Ci-C8)-Alkylsulfonimidoyl, (Ci-C8)- Alkylsulfonylaminocarbonyl, (Ca-Cs)-
Cycloalkylsulfonylaminocarbonyl, Aryl-(Ci-Cs)-alkylcarbonylamino, (C3-C8)-Cycloalkyl-(CrC8)-alkylcarbonylamino, Heteroarylcarbonylamino, (Ci-C8)-Alkoxy-(Ci-C8)-alkylcarbonylamino, Hydroxy-Cd-Cs)- alkylcarbonylamino, (CrC8)-Alkoxycarbonylamino-(Ci-C8)- alkylcarbonylamino, Cyano, Cyano-(Ci-C8)-alkyl, Hydroxycarbonyl, Arylaminosulfonyl, aryl (Ci-C8) -alkylaminosulfonyl, (Ci-C8) alkylsulfonyl, (C 3 -C 8) cycloalkylsulfonyl, arylsulfonyl, (Ci-C8) alkylsulfinyl, (C 3 -C 8) - Cycioalkylsulfinyl, arylsulfinyl, NS-bis [(Ci-C 8) alkyl] sulfonimidoyl, S- (Ci-C8) -Alkylsulfonimidoyl, (Ci-C 8) - alkylsulfonylaminocarbonyl, (Ca-Cs) - Cycloalkylsulfonylaminocarbonyl, aryl- (C 1 -C 8) -alkylcarbonylamino, (C 3 -C 8) -cycloalkyl- (C 1 -C 8) -alkylcarbonylamino, heteroarylcarbonylamino, (C 1 -C 8) -alkoxy- (C 1 -C 8) -alkylcarbonylamino, hydroxy-Cd-Cs) alkylcarbonylamino, (C 1 -C 8) -alkoxycarbonylamino- (C 1 -C 8) -alkylcarbonylamino, cyano, cyano- (C 1 -C 8) -alkyl, hydroxycarbonyl,
(Ci-C8)-Alkoxycarbonyl, (Ca-CeJ-Cycloalkoxycarbonyl, (Cs-CeJ-Cycloalkyl- (d-CeJ-alkoxycarbonyl, Aryloxycarbonyl, Aryl-(d-C8)-alkoxycarbonyl, (C2-C8)-Alkenyloxycarbonyl, (C2-C8)-Alkinyloxycarbonyl, (Ci-Ce)- Haloalkyloxycarbonyl, (Ci-C8)-Alkoxy-(Ci-C8)-alkoxycarbonyl, (C2-C-8)- Alkenyloxy-(Ci-C8)-alkoxycarbonyl, (Ci-C8)-Alkylamino-(Ci-C8)- alkoxycarbonyl, Ths[(Ci-C8)-alkyl]silyloxy-(CrC8)-alkoxycarbonyl, Bis[(Ci-C8)-Alkyl]amino-(Ci-C8)-alkoxycarbonyl, (Ci-Ce)-Alkyl[(Ci-Ce)- alkyl]amino-(Ci-C8)-alkoxycarbonyl, Cyano-(Ci-C8)-alkoxycarbonyl, Heterocyclyl-N-(Ci-C8)-alkoxycarbonyl, Heteroaryloxycarbonyl, (C 1 -C 8) -alkoxycarbonyl, (C 1 -C 12 -cycloalkoxycarbonyl, (C 5 -C 12) -cycloalkyl- (C 1 -C 6 -alkoxycarbonyl, aryloxycarbonyl, aryl- (C 1 -C 8) -alkoxycarbonyl, (C 2 -C 8) -alkenyloxycarbonyl, ( C 2 -C 8) -alkynyloxycarbonyl, (C 1 -C 6) -haloalkyloxycarbonyl, (C 1 -C 8) -alkoxy- (C 1 -C 8) -alkoxycarbonyl, (C 2 -C 8) -alkenyloxy- (C 1 -C 8) -alkoxycarbonyl, ( C 1 -C 8) -Alkylamino- (C 1 -C 8) -alkoxycarbonyl, Ths [(C 1 -C 8) -alkyl] silyloxy- (C 1 -C 8) -alkoxycarbonyl, bis [(C 1 -C 8 ) -alkyl] amino- (C 1 -C 8 ) -alkoxycarbonyl, (C 1 -C 6) -alkyl [(C 1 -C 6) -alkyl] amino- (C 1 -C 8) -alkoxycarbonyl, cyano- (C 1 -C 8) -alkoxycarbonyl, heterocyclyl-N- (C 1 -C 8) - alkoxycarbonyl, heteroaryloxycarbonyl,
Heteroaryl-(CrC8)-alkoxycarbonyl, Heterocyclyl-(CrC8)-alkoxycarbonyl, Heterocyclyl oxycarbonyl , (C2-Cs)-Al kenyl-(Ci-Ce)-al koxycarbonyl , (C2-C8)-Alkinyl-(CrC8)-alkoxycarbonyl, Aryl-(C2-C8)-alkinyloxycarbonyl, Aryl-(C2-C8)-alkenyloxycarbonyl, Aminocarbonyl, (Ci-Cs)- Alkylaminocarbonyl, Bis[(Ci-C8)-alkyl]aminocarbonyl, (Ci-Ce)- Alkyl[(Ci-C8)-Alkyl]aminocarbonyl, (Ci-Ce)-Alkyl[(Ci-Ce)- Alkoxy]aminocarbonyl, (C2-C8)-Alkenylaminocarbonyl, (Ca-Ce)- Cycloalkylaminocarbonyl, Arylaminocarbonyl, Aryl-(Ci-Cs)- alkylaminocarbonyl, Heteroaryl-(CrC8)-alkylaminocarbonyl, Cyano- (Ci-C8)-alkylaminocarbonyl, (CrCeJ-Haloalkylaminocarbonyl, (C2-C-8)- Alkinyl-(Ci-C8)-alkylaminocarbonyl, (Ci-Ce)- Alkoxycarbonylaminocarbonyl, Aryl-(Ci-Ce)- alkoxycarbonylaminocarbonyl, Hydroxycarbonyl-(Ci-C8)-alkyl, (Ci-Cs)- Alkoxycarbonyl-(Ci-C8)-alkyl, (C3-C8)-Cycloalkoxycarbonyl-(Ci-C8)-alkyl, (C3-C8)-Cycloalkyl-(Ci-C8)-alkoxycarbonyl-(Ci-C8)-alkyl, (C2-C8)- Alkenyloxycarbonyl-(d-C8)-alkyl, Aryl-(Ci-C8)-alkoxycarbonyl-(CrC8)- alkyl, (CrC8)-Alkylaminocarbonyl-(Ci-C8)-alkyl, Aminocarbony CrCs)- alkyl, Bis[(Ci-C8)-alkyl]aminocarbonyl-(Ci-C8)-alkyl, (C3-C8)- Cycloalkylaminocarbonyl-(Ci-C8)-alkyl, Aryl-(Ci-C8)-alkylaminocarbonyl- (Ci-Ce)-alkyl, Heteroaryl-(Ci-C8)-alkylaminocarbonyl-(Ci-C8)-alkyL
Cyano-(Ci-C8)-alkylaminocarbonyl-(Ci-C8)-alkyl, (C-i-Cs)- Haloalkylaminocarbonyl-(Ci-C8)-alkyl, (C2-C8)-Alkinyl-(Ci-C8)- alkylaminocarbonyl-(Ci-C8)-alkyl, (C3-C8)-Cycloalkyl-(CrC8)- alkylaminocarbonyl-(CrC8)-alkyl, (Ci-Cs)-Alkoxycarbonylaminocarbonyl- (Ci-Cs)-alkyl, Aryl-(Ci-C8)-alkoxycarbonylaminocarbonyl-(Ci-C8)-alkyl, (Ci-C8)-Alkoxycarbonyl-(Ci-C8)-a!kylaminocarbonyl, Hydroxycarbonyl- (Ci-Cs)-alkylaminocarbonyl, Aryl-(Ci-C8)-alkoxycarbonyl-(Ci-C8)- alkylaminocarbonyl, (Ci-C8)-Alkoxycarbonyl-heterocyclyl-N-carbonyl, (Cr C8)-Alkoxycarbonyl-(Ci-C8)-alky!-heterocyclylidenaminocarbonyl, (Ci-Cs)- Alkoxycarbonylheterocyclyliden-(Ci-Cs)-alky!aminocarbonyl (Ci-Cs)- Alkoxycarbony!-(Ci-C8)-Alkyl((Ci-C8)-alkyl)aminocarbonyl, (d-Cs)- Alkoxycarbonyl-(C3-C8)-cycloalkylidenaminocarbonyli Heterocyclyl-N- carbonyl, (Ci-C8)-Alkoxy-(Ci-C8)-alkylaminocarbonyl, Aminocarbonyl- (Ci-Cs)-alkylaminocarbonyl, (Ci-C8)-Alkylaminocarbonyl-(CrC8)- alkylaminocarbonyl, (C3-C8)-Cycloalkylaminocarbonyl-(Ci-C8)- alkylaminocarbonyl, (C3-C8)-Cycloalkyl-(Ci-C8)-alkylaminocarbonyl, (C3-C8)-Cycloalkyl-(Ci-C8)-alkylaminocarbonyl-(Ci-C8)-alkyl, (C3-C8)- Cycloalkyl-(Ci-C8)-alkylaminocarbonyl-(Ci-C8)-alkylaminocarbonyl, (C2-C8)-Alkenyl-(Ci-Cs)-alkylaminocarbonyl, (C2-Cs)- Alkenylaminocarbonyl-(Ci-Cs)-alkyl, (C2-Cs)-Alkenyl-(Ci-Cs)- alkylaminocarbonyl-(Ci-C8)-alkyl, (Ci-Cs)-Alkylcarbonyl, (Cs-Ce)- Cycloalkylcarbonyl, Arylcarbonyl, Formyl, Hydroxyiminomethyl, Heteroaryl- (C 1 -C 8) -alkoxycarbonyl, heterocyclyl- (C 1 -C 8) -alkoxycarbonyl, heterocyclyloxycarbonyl, (C 2 -C 8) -alkynyl- (C 1 -C 6) -alkoxycarbonyl, (C 2 -C 8) -alkynyl- (C 1 -C 8) -alkoxycarbonyl , Aryl- (C 2 -C 8) -alkynyloxycarbonyl, aryl- (C 2 -C 8) -alkenyloxycarbonyl, aminocarbonyl, (C 1 -C 8) -alkylaminocarbonyl, bis [(C 1 -C 8) -alkyl] aminocarbonyl, (C 1 -C 6) -alkyl [(C 1 -C 8 ) -alkyl] aminocarbonyl, (C 1 -C 6) -alkyl [(C 1 -C 6 ) -alkoxy] -aminocarbonyl, (C 2 -C 8 ) -alkenylaminocarbonyl, (C 2 -C 6) -cycloalkylaminocarbonyl, arylaminocarbonyl, aryl- (C 1 -C 5) -alkylaminocarbonyl, heteroaryl- (C 1 -C 8) -alkylaminocarbonyl, cyano- (C 1 -C 8) -alkylaminocarbonyl, (C 1 -C 6 -haloalkylaminocarbonyl, (C 2 -C 8) -alkynyl- (C 1 -C 8) -alkylaminocarbonyl, ( Ci-Ce) - Alkoxycarbonylaminocarbonyl, aryl- (Ci-Ce) - alkoxycarbonylaminocarbonyl, hydroxycarbonyl- (Ci-C8) -alkyl, (Ci-Cs) - Alkoxycarbonyl- (Ci-C8) -alkyl, (C3-C8) -cycloalkoxycarbonyl - (Ci-C8) alkyl, (C3-C8) -cycloalkyl- (Ci-C8) alkoxycarbonyl (Ci-C8) alkyl, (C 2 -C 8) - alkenyloxycarbonyl (d-C8) alkyl, aryl- (Ci-C8) -alkoxy carbonyl- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylaminocarbonyl- (C 1 -C 8 ) -alkyl, aminocarbonyCrCs) -alkyl, bis [(C 1 -C 8 ) -alkyl] aminocarbonyl- (C 1 -C 8 ) -alkyl, C 3 -C 8 ) -cycloalkylaminocarbonyl- (C 1 -C 8 ) -alkyl, aryl- (C 1 -C 8 ) -alkylaminocarbonyl- (C 1 -C 6 ) -alkyl, heteroaryl- (C 1 -C 8 ) -alkylaminocarbonyl- (C 1 -C 8 ) alkyl Cyano- (C 1 -C 8 ) -alkylaminocarbonyl- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkylaminocarbonyl- (C 1 -C 8 ) -alkyl, (C 2 -C 8 ) -alkynyl- (C 1 -C 8 ) - alkylaminocarbonyl (C 1 -C 8) -alkyl, (C 3 -C 8) -cycloalkyl- (C 1 -C 8) -alkylaminocarbonyl- (C 1 -C 8) -alkyl, (C 1 -C 8) -alkoxycarbonylaminocarbonyl- (C 1 -C 8) -alkyl, aryl- (Ci -C8) -alkoxycarbonylaminocarbonyl- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkoxycarbonyl- (C 1 -C 8 ) -alkylaminocarbonyl, hydroxycarbonyl- (C 1 -C 8 ) -alkylaminocarbonyl, aryl- (C 1 -C 8 -alkyl) 8 ) -alkoxycarbonyl- (C 1 -C 8 ) -alkylaminocarbonyl, (C 1 -C 8 ) -alkoxycarbonyl-heterocyclyl-N-carbonyl, (C 1 -C 8 ) -alkoxycarbonyl- (C 1 -C 8 ) -alky! -Heterocyclylideneaminocarbonyl, (Ci -Cs) - alkoxycarbonylheterocyclyliden- (Ci-Cs) -alky! Aminocarbonyl (Ci-Cs) - alkoxycarbony! - (Ci-C 8 ) -alkyl ((Ci-C 8 ) -alkyl) aminocarbonyl, (d-Cs) - alkoxycarbonyl (C3-C8) -cycloalkylidenaminocarbonyl i heterocyclyl-N- carbonyl, (Ci-C 8) alkoxy (Ci-C8) alkylaminocarbonyl, aminocarbonyl (Ci-Cs) alkylaminocarbonyl, (Ci-C 8) -Alkylaminocarbonyl- (CrC 8 ) -alkylaminocarbonyl, (C 3 -C 8 ) -cycloalky laminocarbonyl- (C 1 -C 8 ) -alkylaminocarbonyl, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 8 ) -alkylaminocarbonyl, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 8 ) -alkylaminocarbonyl- (C 1 -C 8 ) alkyl, (C 3 -C 8) - cycloalkyl (Ci-C8) alkylaminocarbonyl (Ci-C8) alkylaminocarbonyl, (C2-C8) alkenyl (Ci-Cs) alkylaminocarbonyl, (C2 -Cs) - alkenylaminocarbonyl- (C 1 -C 8 ) -alkyl, (C 2 -C 5 ) -alkenyl- (C 1 -C 5 ) -alkylaminocarbonyl- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylcarbonyl, Ce) - cycloalkylcarbonyl, arylcarbonyl, formyl, hydroxyiminomethyl,
Aminoiminomethyl, (Ci-Cs)-Alkoxyiminomet yl, (Ci-C8)- Alkylaminoiminomethyl, Bis[(Ci-C8)-alkyl]aminoiminomethyl, (Cs-Ce)- Cycloalkoxyiminomethyl, (C3-C8)-Cycloalkyl-(Ci-C8)-alkoximinomethyl, Aryloximinomethyl, Ary!-(Ci-C8)-alkoxyiminomethyl, Aryl-(Ci-Cs)- alkylaminoiminomethyl, (C2-Cs)-Alkenyloxyiminomethyl, (Cycloalkoxyiminomethyl, (C3-C8) cycloalkyl - aminoiminomethyl, (Ci-Cs) -Alkoxyiminomet yl, (Ci-C 8) - Alkylaminoiminomethyl, bis [(Ci-C 8) alkyl] aminoiminomethyl, (Cs-Ce) C 1 -C 8 ) -alkoximinomethyl, aryloximinomethyl, aryl- (C 1 -C 8 ) -alkoxyiminomethyl, aryl- (C 1 -C 8 ) -alkylaminoiminomethyl, (C 2 -C 8 ) -alkenyloxyiminomethyl,
Aryiaminoiminomethyl, Arylsuifonylaminoiminomethyl, Heteroaryl-(Ci-Cs)- alkyl, Heterocyclyl-(Ci-C8)-alkyl, Hydroxycarbonylheterocyclyl, (Ci-Cs)- Alkoxycarbonylheterocyclyl, (C2-C8)-Alkenyloxycarbonylheterocyclyl, (C2-C8)-Alkenyl-(Ci-C8)-alkoxycarbonylheterocyclyl, Aryl-(Ci-Cs)- alkoxycarbonylheterocyclyl, (Cs-CsJ-Cycloalkoxycarbonylheterocyclyl, (C3-C8)-Cycloalkyl-(Ci-C8)-alkoxycarbonylheterocyclyl, Aryiaminoiminomethyl, arylsulfonylaminoiminomethyl, heteroaryl- (C 1 -C 8 ) -alkyl, heterocyclyl- (C 1 -C 8) -alkyl, hydroxycarbonyl-heterocyclyl, (C 1 -C 8 ) -alkoxycarbonyl-heterocyclyl, (C 2 -C 8 ) -alkenyloxycarbonyl-heterocyclyl, (C 2 -C 8 ) -alkenyl - (C 1 -C 8 ) -alkoxycarbonylheterocyclyl, aryl- (C 1 -C 5 ) -alkoxycarbonylheterocyclyl, (C 5 -C 8 -cycloalkoxycarbonylheterocyclyl, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 8 ) -alkoxycarbonylheterocyclyl,
Aminocarbonylheterocyclyl, (CrC8)-Alkylaminocarbonylheterocyclyl,
Bis[(Ci-C8)-Alkyl]aminocarbonylheterocyclyl, (Ca-Cs)- Cycloalkylaminocarbonylheterocyclyl, Aryl-(d-C8)- alkylaminocarbonylheterocyclyl, (C2-C8)-Aminocarbonylheterocyclyl, (CrC8) -alkylaminocarbonylheterocyclyl, Bis [(Ci-C8) alkyl] aminocarbonylheterocyclyl, (Ca-Cs) - Cycloalkylaminocarbonylheterocyclyl, aryl (dC 8) - alkylaminocarbonylheterocyclyl, (C2-C8) -
Alkenylaminocarbonylheterocyclyl, Hydroxycarbonylheterocyclyl-(Ci-C8)- alkyl, (Ci-C8)-Alkoxycarbonylheterocyclyl-(CrC8)-alkyl, Hydroxycarbonyl-Alkenylaminocarbonylheterocyclyl, hydroxycarbonylheterocyclyl- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkoxycarbonylheterocyclyl- (C 1 -C 8) -alkyl, hydroxycarbonyl-
(C3-C8)-cycloa!kyl-(Ci-C8)-alkyl, (Ci-C8)-Alkoxycarbonyl-(C3-C8)- cycloalkyl-(CrC8)-alkyl, Hydroxyaminocarbonyl, (Ci-C8)- Alkoxyaminocarbonyl, Aryl-(Ci-C8)-alkoxyaminocarbonyl, Heterocyclyl, (Ci-C8)-Alkylcarbonyloxy, Arylcarbonyloxy, Heteroarylcarbonyloxy, ! (C3-C8) -cycloa alkyl- (Ci-C8) alkyl, (Ci-C8) alkoxycarbonyl (C 3 -C 8) - cycloalkyl- (CRC8) alkyl, hydroxyaminocarbonyl, (Ci- C 8 ) - alkoxyaminocarbonyl, aryl- (C 1 -C 8 ) -alkoxyaminocarbonyl, heterocyclyl, (C 1 -C 8 ) -alkylcarbonyloxy, arylcarbonyloxy, heteroarylcarbonyloxy,
(Ca-CeJ-Cycloalkylcarbonyloxy, (Ci-C8)-Alkoxycarbonyloxy, (C2-C8)- Alkenyloxycarbonyloxy steht, (C 1 -C 12 -cycloalkylcarbonyloxy, (C 1 -C 8 ) -alkoxycarbonyloxy, (C 2 -C 8 ) -alkenyloxycarbonyloxy,
R7, R8 , R9 und R10 unabhängig voneinander für Wasserstoff, Halogen, Nitro,R 7 , R 8 , R 9 and R 10 independently of one another represent hydrogen, halogen, nitro,
Amino, Cyano, (Ci-Cs)-Alkyl, Aryl, Heteroaryl, (C3-C8)-Cycloalkyl, (C4-C8)- Cycloalkenyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (C2-Ce)-Alkenyl-(Ci-Ce)- alkyl, (C2-C8)-Alkinyl-(Ci-C8)-alkyl, Hydroxy, (Ci-Cs)-Alkoxy, (Ci-C8)- Alkoxy-(CrC8)-alkoxy, (Ci-C8)-Alkoxy-(Ci-C8)-alkyl, Hydroxy-(Ci-C8)- alkyl, (Ci-Cs)-Haloalkoxy, (Ci-C8)-Haloalkyl, (C2-C8)-Haloalkenyl, (C2-C8)- Haloalkinyl, (Ci-C8)-Haloalkoxy-(Ci-C8)-alkyl, (Ci-C8)-Alkoxy-(Ci-C8)- haloalkyl, (Ci-C8)-Haloalkoxy-(Ci-C8)-haloalkyl, Hydrothio, (Ci-Cs)- Alkylthio, (CrC8)-Haloalkylthio, (Ci-C8)-Alkylthio-(Ci-C8)-alkyl, (d-C8)- Haloalkylthio-(CrC8)-alkyl, (Ci-C8)-Alkylamino, Bis[(Ci-C8)-alkyl]amino, (C2-C8)-Alkenylamino, (C3-C8)-Cycloalkylamino, (Ci-C8)- Alkylcarbonylamino, (C3-C8)-Cycloalkylcarbonylamino, Amino, cyano, (C 1 -C 8 ) -alkyl, aryl, heteroaryl, (C 3 -C 8 ) -cycloalkyl, (C 4 -C 8 ) -cycloalkenyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -Alkynyl, (C 2 -C 6 ) -alkenyl- (C 1 -C 6 ) -alkyl, (C 2 -C 8 ) -alkynyl- (C 1 -C 8 ) -alkyl, hydroxy, (C 1 -C 5 ) -alkoxy, ( Ci-C8) - alkoxy (-C 8) alkoxy, (Ci-C 8) alkoxy (Ci-C 8) alkyl, hydroxy (Ci-C 8) - alkyl, (Ci-Cs) - haloalkoxy, (Ci-C 8) haloalkyl, (C 2 -C 8) -haloalkenyl, (C 2 -C 8) - haloalkynyl, (Ci-C8) haloalkoxy (Ci-C 8) alkyl, ( C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) -haloalkoxy- (C 1 -C 8 ) -haloalkyl, hydrothio, (C 1 -C 8 ) -alkylthio, (C 1 -C 8 ) - haloalkylthio, (Ci-C8) alkylthio (Ci-C8) alkyl, (dC 8) - Haloalkylthio- (-C 8) alkyl, (Ci-C 8) alkylamino, bis [(Ci-C 8 ) alkyl] amino, (C2-C8) -alkenylamino, (C3-C8) cycloalkylamino, (Ci-C 8) - alkylcarbonylamino, (C3-C8) -Cycloalkylcarbonylamino,
Arylcarbonylamino, Heteroarylcarbonylamino, Formylamino, (Ci-C8)- Haloalkylcarbonylamino, (CrC8)-Alkoxycarbonylamino, (Ci-C8)- Alkylaminocarbonylamino, (Ci-C8)-Alkyl[(Ci-C8)- Alkyl]aminocarbonylamino, (Ci-C8)-Alkylsulfonylamino, (Ca-Cs)- Cycloalkylsulfonylamino, Arylsulfonylamino, Hetarylsulfonylamino, Sulfonyl-(CrC8)-haloalkylamino, Amino-(Ci-C8)-alkylsulfonyl, Amino- (Ci-Cs)-haloalkylsulfonyl, (CrC8)-Alkylaminosulfonyl, Bis[(Ci-C8)- alkyljaminosulfonyl, (C3-C8)-Cycloalkylaminosulfonyl, (Ci-C8)- Haloalkylaminosulfonyl, Heteroarylaminosuifonyi, Arylaminosuifonyi, Aryl- (CrC8)-alkylaminosulfonyl, (Ci-C8)-Alkylsulfonyl, (C3-C8)-
Cycloalkylsulfonyl, Arylsulfonyl, Hydroxycarbonyi, (Ci-Cs)- Alkoxycarbonyl, (Ca-CeJ-Cycloalkoxycarbonyl, (C3-Ce)-Cycloalkyl-(Ci-C8)- alkoxycarbonyl, Aryloxycarbonyl, Aryl-(Ci-C8)-alkoxycarbonyl, (C2-C-8)- Alkenyloxycarbonyl, (C2-C8)-Alkinyloxycarbonyl, Aminocarbonyl, (Ci-Cs)- Alkylaminocarbonyl, Bis[(Ci-C8)-alkyl]aminocarbonyl, (Ci-Cs)- Alkyl[(Ci-C8)-Alkyl]aminocarbonyl, (Ci-C8)-Alkyl[(Ci-C8)- Alkoxy]aminocarbonyl, (C2-C8)-Alkenylaminocarbonyl, (Cs-Ce)- Cycloalkylaminocarbonyl, Arylaminocarbonyl, AryKd-Ce)- alkylaminocarbonyl stehen, Arylcarbonylamino, heteroarylcarbonylamino, formylamino, (Ci-C 8) - Haloalkylcarbonylamino, (CrC 8) alkoxycarbonylamino, (Ci-C 8) - alkylaminocarbonylamino, (Ci-C 8) alkyl [(Ci-C 8) - alkyl] aminocarbonylamino , (Ci-C8) alkylsulfonylamino, (Ca-Cs) - cycloalkylsulfonylamino, arylsulfonylamino, Hetarylsulfonylamino, sulfonyl (CRC 8) -haloalkylamino, amino (Ci-C8) alkylsulfonyl, amino (Ci-Cs) - haloalkylsulfonyl, (CrC 8) alkylaminosulfonyl, bis [(Ci-C 8) - alkyljaminosulfonyl, (C3-C8) -Cycloalkylaminosulfonyl, (Ci-C 8) - Haloalkylaminosulfonyl, Heteroarylaminosuifonyi, Arylaminosuifonyi, aryl (CRC 8) alkylaminosulfonyl , (Ci-C8) alkylsulfonyl, (C 3 -C 8) - Cycloalkylsulfonyl, arylsulfonyl, hydroxycarbonyi, (Ci-Cs) - alkoxycarbonyl, (Ca-CeJ-cycloalkoxycarbonyl, (C3-Ce) -cycloalkyl- (Ci-C8) -alkoxycarbonyl, aryloxycarbonyl, aryl- (Ci-C8) -alkoxycarbonyl, ( C2-C-8) - alkenyloxycarbonyl, (C 2 -C 8) -alkynyloxycarbonyl, aminocarbonyl, (C 1 -C 8) -alkylaminocarbonyl, bis [(C 1 -C 8) -alkyl] aminocarbonyl, (C 1 -C 5) -alkyl [( C 8 ) -alkyl] aminocarbonyl, (C 1 -C 8 ) -alkyl [(C 1 -C 8 ) -alkoxy] -aminocarbonyl, (C 2 -C 8 ) -alkenylaminocarbonyl, (Cs-Ce) -cycloalkylaminocarbonyl, arylaminocarbonyl, AryKd-Ce) - alkylaminocarbonyl,
A1, A2, A3 und A4 gleich oder verschieden sind und unabhängig voneinander für N (Stickstoff) oder die Gruppierungen C-H, C-CH3, C-F, C-Cl, C-Br, C-l, C-OCF3, C-OCH3, C-CF3, C-CO2H, C-CO2CH3 stehen, wobei jedoch in keinem Fall mehr als zwei -Atome benachbart sind, A 1 , A 2 , A 3 and A 4 are the same or different and are each independently N (nitrogen) or the groupings CH, C-CH 3 , CF, C-Cl, C-Br, Cl, C-OCF 3, C -OCH 3, C-CF 3, C-CO2H, C-CO2CH3 are, but in no case more than two -atoms are adjacent,
R11 und R12 unabhängig voneinander für Wasserstoff, Halogen, (Ci-Ce)-Alkyl, Aryl, Heteroaryl, Heterocyclyl, (Cs-CeJ-Cycloalkyl, (C2-Ce)-Alkenyl, (C2-C8)-Alkinyl. (Ci-Ce)-Alkoxy, (Ci-C8)-Alkoxy-(Ci-C8)-alkyl, Aryloxy- (Ci-C8)-alkyl, (Ci-Cs)-Haloalkoxy, (Ci-C8)-Haloalkyl, (Ci-C8)-Haloalkoxy- (Ci-Cs)-alkyl, (Ci-C8)-Alkoxy-(Ci-C8)-haloalkyl, (Ci-C8)-Haloalkoxy- (d-C8)-haloalkyl, (Ci-C8)-Alkylthio, (d-C8)-Haloalkylthio, (d-C8)- Alkylthio-(Ci-C8)-alkyl, Hydroxycarbonyi, (Ci-C8)-Alkoxycarbonyl, (Ca-Cs)- Cycloalkoxycarbonyl, (C3-C8)-Cycloalkyl-(CrC8)-alkoxycarbonyl, R 11 and R 12 independently of one another represent hydrogen, halogen, (C 1 -C 6) -alkyl, aryl, heteroaryl, heterocyclyl, (C 5 -C 12 -cycloalkyl, (C 2 -C 6) -alkenyl, (C 2 -C 8 ) -alkynyl. (Ci-Ce) alkoxy, (Ci-C 8) alkoxy (Ci-C 8) alkyl, aryloxy (Ci-C8) alkyl, (Ci-Cs) haloalkoxy, (Ci-C 8 ) -haloalkyl, (Ci-C8) haloalkoxy (Ci-Cs) alkyl, (Ci-C 8) alkoxy (Ci-C 8) haloalkyl, (Ci-C8) haloalkoxy (dC 8) -haloalkyl, (Ci-C8) alkylthio, (dC 8) haloalkylthio, (dC 8) - alkylthio (Ci-C8) alkyl, Hydroxycarbonyi, (Ci-C8) alkoxycarbonyl, (Ca -Cs) - cycloalkoxycarbonyl, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 8 ) -alkoxycarbonyl,
Aryloxycarbonyl, Aryl-(Ci-C8)-alkoxycarbonyl, (C2-C8)- Alkenyloxycarbonyl, (C2-C8)-Alkinyloxycarbonyl, Aminocarbonyl, (Ci-C8)- Alkylaminocarbonyl, Bis[(CrC8)-alkyl]aminocarbonyl, (Ci-C8)- Alkyl[(Ci-C8)-Alkyl]aminocarbonyl, (Ci-C8)-Alkyl[(Ci-C8)- Alkoxyjaminocarbonyl, (C2-C8)-Alkenylaminocarbonyl, (Ca-Cs)- Cycloalkylaminocarbonyl, Arylaminocarbonyl, Aryl-(Ci-Ce)- alkylaminocarbonyl stehen, Aryloxycarbonyl, aryl (Ci-C8) -alkoxycarbonyl, (C2-C8) - alkenyloxycarbonyl, (C2-C8) -alkynyloxycarbonyl, aminocarbonyl, (Ci-C8) - alkylaminocarbonyl, bis [(-C 8) alkyl ] aminocarbonyl, (Ci-C 8) - alkyl [(Ci-C 8) alkyl] aminocarbonyl, (Ci-C 8) alkyl [(Ci-C 8) - Alkoxyjaminocarbonyl, (C2-C8) -Alkenylaminocarbonyl, (Ca-Cs) - cycloalkylaminocarbonyl, arylaminocarbonyl, aryl- (Ci-Ce) - alkylaminocarbonyl,
A5 für S (Schwefel), O (Sauerstoff) oder die Gruppierungen N-H, N-CH3, N- CH2CH3, N-CH(CH3)2, N-C02t-Bu, N-Aryl, N-Heteroaryl, N-Heterocyclyl steht.
R13, R14, R17 und R18 unabhängig voneinander für Wasserstoff, (C-i-C-8)-Alkyl, Halogen, (C3-C-8)-Cycloalkyl, Aryl, Heteroaryl, Heterocyclyl, (Cz-Ce)- Alkenyl, (C2-C8)-Alkenyl-(Ci-C8)-alkyl, Aryl-(Ci-C8)-alkyl, (CrC8)-Alkoxy, (Ci-C8)-Alkoxy-(Ci-C8)-alkoxy, (Ci-C8)-Alkoxy-(d-C8)-alkyl, Hydroxy, (CrC8)-Haloalkyl, (Ci-C8)-Haloalkylthio stehen oder A 5 represents S (sulfur), O (oxygen) or the groupings NH, N-CH 3 , N-CH 2 CH 3 , N-CH (CH 3 ) 2, N-CO 2 t-Bu, N-aryl, N-heteroaryl, N-heterocyclyl is. R 13 , R 14 , R 17 and R 18 independently of one another represent hydrogen, (C 1 -C 8) -alkyl, halogen, (C 3 -C 8) -cycloalkyl, aryl, heteroaryl, heterocyclyl, (C 1 -C 6) -alkenyl, (C2-C8) alkenyl (Ci-C 8) alkyl, aryl (Ci-C8) alkyl, (CrC 8) -alkoxy, (Ci-C 8) alkoxy (Ci-C 8) alkoxy, (C 1 -C 8 ) alkoxy- (C 1 -C 8 ) -alkyl, hydroxy, (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) -haloalkylthio, or
R13 und R17 mit den Atomen, an die sie gebunden sind, einen vollständig R 13 and R 17 complete with the atoms to which they are attached
gesättigten oder teilgesättigten, gegebenenfalls weiter substituierten 5 bis 7-gliedrigen Ring bilden, form a saturated or partially saturated, optionally further substituted 5 to 7-membered ring,
A6, A7 gleich oder verschieden sind und unabhängig voneinander für O A 6 , A 7 are the same or different and are each independently O.
(Sauerstoff), S (Schwefel), N-H, N-OCH3, N-CH3 oder die Gruppierung CR15R16 stehen, wobei jedoch in keinem Fall zwei N-, O- oder S-Atome benachbart sind, und wobei R15 und R16 in der Gruppierung CR15R16 jeweils gleiche oder verschiedene Bedeutungen gemäß der (Oxygen), S (sulfur), NH, N-OCH 3 , N-CH 3 or the group CR 15 R 16 , but in no case are two N, O or S atoms adjacent, and R 15 and R 16 in the group CR 15 R 16 each have the same or different meanings according to the
nachstehenden Definition haben und have the following definition and
R15 und R16 unabhängig voneinander für Wasserstoff, Halogen, (Ci-Cs)-Alkyl, Aryl, Heteroaryl, Heterocyclyl, (C3-C8)-Cycloalkyl, (C2-C8)-Alkenyl, R 15 and R 16 independently of one another are hydrogen, halogen, (C 1 -C 5) -alkyl, aryl, heteroaryl, heterocyclyl, (C 3 -C 8 ) -cycloalkyl, (C 2 -C 8 ) -alkenyl,
(CrCs)-Alkoxy, (Ci-C8)-Alkoxy-(Ci-C8)-alkyl, Aryloxy-(d-C8)-alkyl, (C 1 -C 6) -alkoxy, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, aryloxy- (C 1 -C 8 ) -alkyl,
(Ci-C8)-Haloalkoxy, (Ci-C8)-Haloalkyl, (CrC8)-Haloalkoxy(Ci-C8)-alkyl, (Ci-C8)-Alkoxy-(Ci-C8)-haloalkyl, (Ci-C8)-Haloalkoxy-(d-C8)-haloalkyl, (CrC8)-Alkylthio, (Ci-C8)-Haloalkylthio, (Ci-C8)-Alkylthio-(Ci-C8)-alkyl, Hydroxycarbonyl, (Ci-C8)-Alkoxycarbonyl, (C:rC8)-Cycloalkoxycarbonyl, (C3-C8)-Cycloalkyl-(CrC8)-alkoxycarbonyl, Aryloxycarbonyl, Aryl-(d-C8)- alkoxycarbonyl , (C2-C8)-Alkenyloxycarbonyl , (C2-C8)-Al ki nyloxycarbonyl , Aminocarbonyl, (Ci-C8)-Alkylaminocarbonyl, Bis[(Ci-C8)- alkyljaminocarbonyl, (Ci-C8)-Alkyl[(Ci-C8)-Alkyl]aminocarbonyl, (Ci-C8)- Alkyl[(Ci-C8)-Alkoxy]aminocarbonyl, (C2-C8)-Alkenylaminocarbonyl, (Ci-C8) -haloalkoxy, (Ci-C 8) haloalkyl, (CrC 8) haloalkoxy (Ci-C 8) alkyl, (Ci-C 8) alkoxy (Ci-C8) -haloalkyl , (Ci-C8) haloalkoxy (dC 8) -haloalkyl, (CrC 8) alkylthio, (Ci-C8) haloalkylthio, (Ci-C8) alkylthio (Ci-C8) alkyl , hydroxycarbonyl, (Ci-C8) alkoxycarbonyl, (C rC 8) -cycloalkoxycarbonyl, (C3-C8) cycloalkyl (CrC 8) -alkoxycarbonyl, aryloxycarbonyl, aryl (dC 8) - alkoxycarbonyl, (C2 -C 8) alkenyloxycarbonyl, (C2-C8) -alkyl ki nyloxycarbonyl, aminocarbonyl, (Ci-C 8) alkylaminocarbonyl, bis [(Ci-C 8) - alkyljaminocarbonyl, (Ci-C (8) alkyl [ Ci-C 8) alkyl] aminocarbonyl, (Ci-C 8) - alkyl [(Ci-C 8) alkoxy] aminocarbonyl, (C2-C8) -Alkenylaminocarbonyl,
(C3-C8)-Cycloalkylaminocarbonyl, Arylaminocarbonyl, Aryl-(d-C8)- alkylaminocarbonyl, Amino, (d-C8)-Alkylamino, (C3-C8)-Cycloalkylamino, Bis-[(Ci-C8)-Alkyl]amino stehen,
R19, R20, R22 und R23 unabhängig voneinander für Wasserstoff, (Ci-Cs)-Alkyl, Halogen, (C3-C8)-Cycioalkyl, Aryl, Heteroaryi, Heterocyciyl, (C2-C-8)- Alkenyl, Aryl-(Ci-C8)-alkyl. (Ci-C8)-Alkoxy, (Ci-C8)-Alkoxy-(CrC8)-alkoxy, (CrC8)-Alkoxy-(Ci-C8)-alkyl, (d-C8)-Haloalkyl stehen, (C 3 -C 8 ) -cycloalkylaminocarbonyl, arylaminocarbonyl, aryl- (C 1 -C 8 ) -alkylaminocarbonyl, amino, (C 1 -C 8 ) -alkylamino, (C 3 -C 8 ) -cycloalkylamino, bis - [(C 1 -C 8 ) -alkyl] amino, R 19 , R 20 , R 22 and R 23 independently of one another represent hydrogen, (C 1 -C 5) -alkyl, halogen, (C 3 -C 8) -cycloalkyl, aryl, heteroaryl, heterocyclic, (C 2 -C 8) -alkenyl, Aryl- (C 1 -C 8 ) -alkyl. (C 1 -C 8 ) -alkoxy, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkoxy, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkyl,
A8 für O (Sauerstoff), S (Schwefel), N-H, N-CH3, N-OCH3 oder die Gruppierung CHR21 steht und wobei R21 in der Gruppierung CHR21 die Bedeutung gemäß der nachstehenden Definition hat, A 8 is O (oxygen), S (sulfur), NH, N-CH 3 , N-OCH 3 or the moiety CHR 21 , and wherein R 21 in the moiety CHR 21 has the meaning as defined below,
R21 für Wasserstoff, Halogen, (Ci-Cs)-Alkyl, Aryl, Heteroaryi, Heterocyciyl, R 21 is hydrogen, halogen, (C 1 -C 5) -alkyl, aryl, heteroaryl, heterocyciyl,
(C3-C8)-Cycloalkyl, (C2-C8)-Alkenyl, (Ci-C8)-Alkoxy, (d-C8)-Alkoxy- (CrCs)-alkyl, Aryloxy-(CrC8)-alkyl, (d-C8)-Haloalkoxy, (Ci-C8)-Haloalkyl, (Ci-C8)-Alkoxy-(Ci-C8)-haloalkyl, (Ci-C8)-Haloalkoxy-(CrC8)-haloalkyl, (d-C8)-Alkylthio, (d-C8)-Haloalkylthio, (Ci-C8)-Alkylthio(Ci-C8)-alkyl, Hydroxycarbonyl, (CrC8)-Alkoxycarbonyl, (C:i-C8)-Cycloalkoxycarbonyl, Aryl-(CrC8)-alkoxycarbonyl, (C2-C8)-Alkenyloxycarbonyl, (C2-C8)- Alkinyloxycarbonyl, Aminocarbonyl, (Ci-Cs)-Alkylaminocarbonyl, (C 3 -C 8) cycloalkyl, (C 2 -C 8) alkenyl, (Ci-C 8) alkoxy, (DC 8) alkoxy- (CRCs) alkyl, aryloxy- (CrC 8) alkyl , (C 1 -C 8 ) -haloalkoxy, (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) -haloalkoxy- (C 1 -C 8 ) -haloalkyl , (dC 8) alkylthio, (dC 8) haloalkylthio, (Ci-C8) alkylthio (Ci-C8) alkyl, hydroxycarbonyl, (CrC 8) alkoxycarbonyl, (C: iC 8) -cycloalkoxycarbonyl, Aryl- (C 1 -C 8 ) -alkoxycarbonyl, (C 2 -C 8 ) -alkenyloxycarbonyl, (C 2 -C 8 ) -alkynyloxycarbonyl, aminocarbonyl, (C 1 -C 8 ) -alkylaminocarbonyl,
Bis[(Ci-C8)-alkyl]aminocarbonyl, (Ci-C8)-Alkyl[(Ci-C8)- Alkyljaminocarbonyl, (Ci-C8)-Alkyl[(Ci-C8)-Alkoxy]aminocarbonyl, (C2-C8)-Alkenylaminocarbonyl, (C3-C8)-Cycloalkylaminocarbonyl, Bis [(Ci-C 8) alkyl] aminocarbonyl, (Ci-C 8) alkyl [(Ci-C 8) - Alkyljaminocarbonyl, (Ci-C 8) alkyl [(Ci-C 8) alkoxy] aminocarbonyl , (C 2 -C 8 ) -alkenylaminocarbonyl, (C 3 -C 8 ) -cycloalkylaminocarbonyl,
Arylaminocarbonyl, Aryl-(CrC8)-alkylaminocarbonyl, Amino, (d-C8)- Alkylamino, (C3-C8)-Cycloalkylamino, Bis[(Ci-C8)-Alkyl]amino steht, Arylaminocarbonyl, aryl (-C 8) alkylaminocarbonyl, amino, (DC 8) - alkylamino, (C3-C8) cycloalkylamino, bis [(Ci-C 8) alkyl] amino is,
R24, R25, R26, R28, R29 und R30 unabhängig voneinander für Wasserstoff, (Ci-C8)- Alkyl, Halogen, (C3-C8)-Cycloalkyl, Aryl, Heteroaryi, Heterocyciyl, (C2-C-8)- Alkenyl, (CrCs)-Alkoxy, (Ci-C8)-Alkoxy-(Ci-C8)-alkoxy, (Ci-Cs)-Alkoxy- (Ci-Cs)-alkyl, (Ci-C8)-Haloalkyl, (Ci-Cs)-Alkylthio, (Ci-Ce)-Haloalkylthio stehen, R 24, R 25, R 26, R 28, R 29 and R 30 are independently hydrogen, (Ci-C 8) - alkyl, halogen, (C3-C8) cycloalkyl, aryl, heteroaryl, Heterocyciyl, (C2 -C-8) - alkenyl, (C 1 -C 6) alkoxy, (C 1 -C 8 ) alkoxy- (C 1 -C 8 ) -alkoxy, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, (Ci -C 8 ) -haloalkyl, (C 1 -C 8 ) -alkylthio, (C 1 -C 6 ) -haloalkylthio,
A9 für O (Sauerstoff), S (Schwefel), N-H, N-CH3, N-OCH3 oder die Gruppierung CHR27 steht und wobei R27 in der Gruppierung CHR27 die Bedeutung gemäß der nachstehenden Definition hat und
R27 für Wasserstoff, Halogen, (Ci-C8)-Alkyl, Aryl, Heteroaryl, Heterocyclyl, (C3-C8)-Cycloalkyl, (C2-C8)-Alkenyl, (CrC8)-Alkoxy, (Ci-Ce)-Alkoxy- (d-C8)-alkyl, Aryloxy-(Ci-C8)-alkyl, (Ci-C8)-Haloalkoxy, (d-C8)-Haloalkyl, (CrC8)-Alkylthio, (Ci-C8)-Haloalkylthio, Hydroxycarbonyl, (Ci-C8)- Alkoxycarbonyl, (C3-C8)-Cycloalkoxycarbonyl, Aryl-(Ci-C8)- alkoxycarbonyl, (C2-C8)-Alkenyloxycarbonyl, (C2-C8)-Alkinyloxycarbonyl, Aminocarbonyl, (Ci-C8)-Alkylaminocarbonyl, Bis[(d-C8)- alkyljaminocarbonyl, (Ci-C8)-Alkyl[(Ci-C8)-Alkyl]aminocarbonyl, (d-C8)- Alkyl[(Ci-C8)-Alkoxy]aminocarbonyl, (C2-C8)-Alkenylaminocarbonyl, A 9 is O (oxygen), S (sulfur), NH, N-CH 3, N -OCH 3 or the moiety CHR 27 and wherein R 27 in the moiety CHR 27 has the meaning as defined below and R 27 is hydrogen, halogen, (C 1 -C 8 ) -alkyl, aryl, heteroaryl, heterocyclyl, (C 3 -C 8 ) -cycloalkyl, (C 2 -C 8 ) -alkenyl, (C 1 -C 8 ) -alkoxy, ( Ci-Ce) alkoxy (dC 8) alkyl, aryloxy (Ci-C8) alkyl, (Ci-C8) -haloalkoxy, (dC 8) -haloalkyl, (CrC 8) alkylthio, (C -C 8) haloalkylthio, hydroxycarbonyl, (Ci-C8) - alkoxycarbonyl, (C3-C8) -cycloalkoxycarbonyl, aryl (Ci-C8) - alkoxycarbonyl, (C2-C8) alkenyloxycarbonyl, (C2- C 8 ) -alkynyloxycarbonyl, aminocarbonyl, (C 1 -C 8 ) -alkylaminocarbonyl, bis [(C 1 -C 8 ) -alkylaminocarbonyl, (C 1 -C 8 ) -alkyl [(C 1 -C 8 ) -alkyl] aminocarbonyl, (C 1 -C 8 ) Alkyl [(C 1 -C 8 ) -alkoxy] aminocarbonyl, (C 2 -C 8 ) -alkenylaminocarbonyl,
(C3-C8)-Cycloalkylaminocarbonyl, Arylaminocarbonyl, Aryl-(Ci-C8)- alkylaminocarbonyl, Amino, (CrC8)-Alkylamino, (C3-C8)-Cycloalkylamino, Bis[(Ci-C8)-Alkyl]amino steht. (C 3 -C 8 ) -cycloalkylaminocarbonyl, arylaminocarbonyl, aryl- (C 1 -C 8 ) -alkylaminocarbonyl, amino, (C 1 -C 8 ) -alkylamino, (C 3 -C 8 ) -cycloalkylamino, bis [(C 1 -C 8 ) -alkyl ] amino stands.
3. Verwendung gemäß Anspruch 1 , wobei in Formel (I) 3. Use according to claim 1, wherein in formula (I)
[X-Y] für die Gruppierungen [X-Y] for the groupings
[X-Y]1 und [X-Y]2 steht, [XY] 1 and [XY] 2 ,
Q für die Gruppierungen Q-1 bis Q-6 Q for the groupings Q-1 to Q-6
Q-1 Q-2 Q-3 Q-1 Q-2 Q-3
Q-4 Q-5 und Q-6
sieht, wobei R7, R8, R9, R10, R11 , R12, R 3, R14, R17, R 8, R19, R20, R22, R23, R24, R25, R26, R28, R29 und R30 und A1 bis A9 jeweils die Bedeutung gemäß der nachstehenden Definitionen haben und wobei der Pfeil für eine Bindung zur jeweiligen Gruppierung C-R6 in der allgemeinen Q-4 Q-5 and Q-6 where R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 3 , R 14 , R 17 , R 8 , R 19 , R 20 , R 22 , R 23 , R 24 , R 25 , R 26 , R 28 , R 29 and R 30 and A 1 to A 9 each have the meaning as defined below, and wherein the arrow for a bond to the respective group CR 6 in the general
Formel (I) steht, Formula (I) stands,
R1 für (CrC7)-Alkyl, (C3-C7)-Cycloalkyl, (C4-C7)-Cycloalkenyl, (C2-C7)- Alkenyl, (C2-C7)-Alkinyl, (C2-C7)-Alkenyl-(Ci-C7)-alkyl, (C2-C7)-Alkinyl- (Ci-C7)-alkyl, (Ci-C7)-Alkoxy-(Ci-C7)-alkyl, Hydroxy-(Ci-C7)-alkyl, (C1-C7)- Haloalkyl, (C2-C7)-Haloalkenyl, (C2-C7)-Haloalkinyl, (Ci-C7)-Haloalkoxy- (d-C7)-alkyl, (Ci-C7)-Alkoxy-(d-C7)-haloalkyl, (d-C7)-Haloalkoxy- (Ci-C7)-haloalkyl, (Ci-C7)-Alkylthio-(C,-C7)-alkyl. (Ci-C7)-Haloalkylthio- (d-C7)-alkyl steht, R 1 is (C 1 -C 7 ) -alkyl, (C 3 -C 7 ) -cycloalkyl, (C 4 -C 7 ) -cycloalkenyl, (C 2 -C 7 ) -alkenyl, (C 2 -C 7 ) -alkynyl, (C 2 -C 7) alkenyl (Ci-C7) alkyl, (C 2 -C 7) alkynyl (Ci-C7) alkyl, (Ci-C7) alkoxy (Ci-C 7 ) alkyl, hydroxy (Ci-C7) alkyl, (C1-C7) - haloalkyl, (C 2 -C 7) haloalkenyl, (C 2 -C 7) haloalkynyl, (Ci-C7) - haloalkoxy (dC 7) alkyl, (Ci-C7) alkoxy (dC 7) -haloalkyl, (dC 7) haloalkoxy (Ci-C7) haloalkyl, (Ci-C7) -alkylthio (C, -C 7 ) -alkyl. (C 1 -C 7 ) -haloalkylthio (C 1 -C 7 ) -alkyl,
R2, R3 und R4 unabhängig voneinander für Wasserstoff, Halogen, (d-C7)-Alkyl, (C3-C7)-Cycloalkyl, (C4-C7)-Cycloalkenyl, (C2-C7)-Alkenyl, (C2-C7)-Alkinyl, (C2-C7)-Alkenyl-(Ci-C7)-alkyl, (C2-C7)-Alkinyl-(Ci-C7)-alkyl, (C1-C7)- Alkoxy-(Ci-C7)-alkyl, Hydroxy-(Ci-C7)-alkyl, (Ci-C7)-Haloalkyl, (C2-C7)- Haloalkenyl, (C2-C7)-Haloalkinyl, (Ci-C7)-Haloalkoxy-(Ci-C7)-alkyl, (Ci-C7)-Alkoxy-(Ci-C7)-haloalkyl, (Ci-C7)-Haloalkoxy-(Ci-C7)-haloalkyl, (Ci-C7)-Alkylthio-(d-C7)-alkyl, (Ci-C7)-Haloalkylthio-(Ci-C7)-alkyl stehen, R 2, R 3 and R 4 are independently hydrogen, halogen, (dC 7) alkyl, (C 3 -C 7) cycloalkyl, (C 4 -C 7) -cycloalkenyl, (C 2 -C 7) - alkenyl, (C 2 -C 7) -alkynyl, (C 2 -C 7) alkenyl (Ci-C7) alkyl, (C 2 -C 7) alkynyl (Ci-C7) alkyl, (C1-C7) - alkoxy (Ci-C7) alkyl, hydroxy (Ci-C7) alkyl, (Ci-C7) haloalkyl, (C2-C7) - haloalkenyl, (C 2 -C 7 ) -haloalkynyl, (C 1 -C 7 ) -haloalkoxy- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -haloalkoxy- (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -alkylthio (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -haloalkylthio (C 1 -C 7 ) -alkyl,
R5 für Hydroxy, (d-C7)-Alkoxy, Aryloxy, (C3-C7)-Cycloalkyloxy, (C2-C7)- Alkenyloxy, (C2-C7)-Alkenyl-(Ci-C7)-alkyloxy, (Ci-C7)-Alkoxy-(Ci-C7)- alkyloxy, (Ci-C7)-Alkylcarbonyloxy, Arylcarbonyloxy, R 5 is hydroxy, (dC 7 ) alkoxy, aryloxy, (C 3 -C 7 ) -cycloalkyloxy, (C 2 -C 7 ) -alkenyloxy, (C 2 -C 7 ) -alkenyl- (C 1 -C 7 ) -alkyloxy , (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyloxy, (C 1 -C 7 ) -alkylcarbonyloxy, arylcarbonyloxy,
Heteroarylcarbonyloxy, (C3-C7)-Cycloalkylcarbonyloxy, (C1-C7)- Alkoxycarbonyloxy, (C2-C7)-Alkenyloxycarbonyloxy, Aryloxy-(Ci-C7)- alkyloxy, Aryl-(Ci-C7)-alkyloxy, (Ci-C7)-Alkoxy-(Ci-C7)-alkoxy-(Ci-C7)- alkyloxy, (Ci-C7)-Alkylthio-(Ci-C7)-alkyloxy, Tris[(Ci-C7)-alkyl]silyloxy, (CrC7)-Alkyl-Bis[(Ci-C7)-alkyl]silyloxy, (d-C7)-Alkyl-bis(Aryl)silyloxy, Aryl-bis[(CrC7)— alkyljsiiyloxy, Cycloalkyl-bis[(CrC7)-alkyl]silyloxy, Halo- bis[(CrC7)-alkyl]silyloxy, Tris[(Ci-C7)-alkyl]silyl-(CrC7)-alkoxy-(Ci-C7)- alkyloxy steht,
für Nitro, Amino, Hydroxy, Hydrothio, Thiocyanato, Isothiocyanato, Halogen, (CrC7)-Alkyl, (C3-C7)-Cycloalkyl, (C2-C7)-Alkenyl, (C4-C7)- Cycloalkenyl, (C2-C7)-Alkinyl, Aryl-(C2-C7)-alkinyl, Tris[(Ci-C7)-alkyl]silyl- (C2-C7)-alkinyl, Aryi, Aryl-(Ci-C7)-alkyl, Aryl-(d-C7)-alkoxy, Heieroaryl, (CrC7)-Haloalkyl, (C3-C7)-Halocycloalkyl, (C2-C7)-Haloalkenyl, (C1-C7)- Alkoxy, (Ci-C7)-Haloalkoxy, Aryloxy, Heteroaryloxy, (C3-C7)- Cycloalkyloxy, (C3-C7)-Cycloalkyl-(Ci-C7)-alkoxy, (C2-C7)- (C2-C7)- Alkenyloxy, (C2-C7)-Alkinyl-(C2-C7)-alkyloxy, Hydroxy-(Ci-C7)-alkyl, Heteroarylcarbonyloxy, (C3-C 7) cycloalkylcarbonyloxy, (C1-C7) - alkoxycarbonyloxy, (C 2 -C 7) -Alkenyloxycarbonyloxy, aryloxy (Ci-C7) - alkyloxy, aryl- (Ci-C7) alkyloxy , (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyloxy, (C 1 -C 7 ) -alkylthio (C 1 -C 7 ) -alkyloxy, tris [(Ci -C 7 ) -alkyl] silyloxy, (CrC 7 ) -alkyl-bis [(Ci-C 7 ) -alkyl] silyloxy, (dC 7 ) -alkyl-bis (aryl) silyloxy, aryl-bis [(CrC 7 ) Alkylsilyloxy, cycloalkylbis [(CrC 7 ) alkyl] silyloxy, halo bis [(CrC 7 ) alkyl] silyloxy, tris [(Ci-C 7 ) alkyl] silyl (CrC 7 ) alkoxy ( Ci-C 7 ) - alkyloxy, nitro, amino, hydroxy, Hydrothio, thiocyanato, isothiocyanato, halogen, (CrC 7) alkyl, (C 3 -C 7) cycloalkyl, (C 2 -C 7) alkenyl, (C 4 -C 7) - cycloalkenyl, (C 2 -C 7) alkynyl, aryl (C 2 -C 7) alkynyl, tris [(Ci-C 7) alkyl] silyl (C 2 -C 7) alkynyl, Aryi, aryl - (Ci-C 7 ) -alkyl, aryl- (dC 7 ) -alkoxy, Heieroaryl, (CrC 7 ) -haloalkyl, (C 3 -C 7 ) -halocycloalkyl, (C 2 -C 7 ) -haloalkenyl, (C1 -C 7) - alkoxy, (C 1 -C 7 ) -haloalkoxy, aryloxy, heteroaryloxy, (C 3 -C 7 ) -cycloalkyloxy, (C 3 -C 7 ) -cycloalkyl- (C 1 -C 7 ) -alkoxy, (C 2 - C 7 ) - (C 2 -C 7 ) -alkenyloxy, (C 2 -C 7 ) -alkynyl- (C 2 -C 7 ) -alkyloxy, hydroxy- (C 1 -C 7 ) -alkyl,
(Ci-C7)-Alkoxy-(Ci-C7)-alkyl, Aryloxy-(Ci-C7)-alkyl, Heteroaryloxy-(Ci-C7)- alkyl, (Ci-C7)-Alkylthio, (Ci-C7)-Haloalkylthio, (Ci-C7)-Alkoxycarbonyl- (Ci-C7)-alkylthio, Arylthio, (C3-C7)-Cycloalkylthio, Heteroarylthio, (C1-C7)- Alkylthio-(Ci-C7)-alkyl, (Ci-C7)-Alkylamino, Bis[(Ci-C7)-alkyl]amino, (C2-C7)-Alkenylamino, (C3-C7)-Cycloalkylamino, (C1-C7)- Alkylcarbonylamino, (C3-C7)-Cycloalkylcarbonylamino, (Ci-C7) alkoxy (Ci-C7) alkyl, aryloxy (Ci-C7) alkyl, heteroaryloxy- (Ci-C7) - alkyl, (Ci-C7) -alkylthio, ( Ci-C 7) haloalkylthio, (Ci-C 7) alkoxycarbonyl (Ci-C7) alkylthio, arylthio, (C 3 -C 7) cycloalkylthio, heteroarylthio, (C1-C7) - alkylthio (C -C 7) alkyl, (Ci-C7) alkylamino, bis [(Ci-C 7) alkyl] amino, (C 2 -C 7) alkenylamino, (C3-C7) cycloalkylamino, (C1 -C 7) - alkylcarbonylamino, (C 3 -C 7 ) -cycloalkylcarbonylamino,
Arylcarbonylamino, Heteroaryicarbonylamino, Formylamino, (C1-C7)- Haloalkylcarbonylamino, (CrC7)-Alkoxycarbonylamino, (C1-C7)- Alkylaminocarbonylamino, (CrC7)-Alkyl[(Ci-C7)- Alkyl]aminocarbonylamino, (Ci-C7)-Alkylsulfonylamino, (C3-C7)- Cycloalkylsulfonylamino, Arylsulfonylamino, Hetarylsulfonylamino, Sulfonyl-(Ci-C7)-haloalkylamino, Amino-(Ci-C7)-alkylsulfonyl, Amino- (CrC7)-haloalkylsulfonyl, (Ci-C7)-Alkylaminosulfonyl, Bis[(d-C7)- alkyl]aminosulfonyl, (C3-C7)-Cycloalkylaminosulfonyl, (C1-C7)- Haloalkylaminosulfonyl, Aminosulfonyl, Heteroarylaminosulfonyl, Arylcarbonylamino, Heteroaryicarbonylamino, formylamino, (C1-C7) - Haloalkylcarbonylamino, (CrC 7) alkoxycarbonylamino, (C1-C7) - alkylaminocarbonylamino, (CrC 7) alkyl [(Ci-C7) - alkyl] aminocarbonylamino, (Ci- C 7 ) -alkylsulfonylamino, (C 3 -C 7 ) -cycloalkylsulfonylamino, arylsulfonylamino, hetarylsulfonylamino, sulfonyl- (C 1 -C 7 ) -haloalkylamino, amino- (C 1 -C 7 ) -alkylsulfonyl, amino- (C 1 -C 7 ) -haloalkylsulfonyl, ( Ci-C 7) alkylaminosulfonyl, bis [(dC 7) - alkyl] aminosulfonyl, (C3-C 7) -Cycloalkylaminosulfonyl, (C1-C7) - Haloalkylaminosulfonyl, aminosulfonyl, heteroarylaminosulfonyl,
Arylaminosulfonyl, Aryl-(Ci-C7)-alkylaminosulfonyl, (d-C7)-Alkylsulfonyl, (C3-C7)-Cycloalkylsulfonyl, Arylsulfonyl, (CrC7)-Alkylsulfinyl, (C3-C7)- Cycloalkylsulfinyl, Arylsulfinyl, N.S-Bis[(CrC7)-alkyl]sulfonimidoyl, S- (Ci-C7)-Alkylsulfonimidoyl, (C1-C7)- Alkylsulfonylaminocarbonyl, (C3-C7)- Cycloalkylsulfonylaminocarbonyl, Aryl-(Ci-C7)-alkylcarbonylamino, Arylaminosulfonyl, aryl- (Ci-C7) alkylaminosulfonyl, (dC 7) alkylsulfonyl, (C 3 -C 7) cycloalkylsulfonyl, arylsulfonyl, (CrC 7) alkylsulfinyl, (C3-C7) - cycloalkylsulfinyl, arylsulfinyl, NS -Bis [(C 1 -C 7 ) -alkyl] sulfonimidoyl, S- (C 1 -C 7 ) -alkylsulfonimidoyl, (C 1 -C 7 ) -alkylsulfonylaminocarbonyl, (C 3 -C 7 ) -cycloalkylsulfonylaminocarbonyl, aryl- (C 1 -C 7 ) -alkylcarbonylamino,
(C3-C7)-Cycloalkyl-(Ci-C7)-alkylcarbonylamino, Heteroaryicarbonylamino, (CrC7)-Alkoxy-(Ci-C7)-alkylcarbonylamino, Hydroxy-(CrC7)- alkylcarbonylamino, (Ci-C7)-Alkoxycarbonylamino-(Ci-C7)- alkylcarbonylamino, Cyano, Cyano-(CrC7)-alkyl, Hydroxycarbonyl, (d-C7)-Alkoxycarbonyl, (C3-C7)-Cycloalkoxycarbonyl, (C3-C7)-Cycloalkyl- (Ci-C7)-alkoxycarbonyl, Aryloxycarbonyl, Aryl-(d-C7)-alkoxycarbonyl,
(C2-C-7)-Alkenyloxycarbonyl, (C2-C-7)-Alkinyloxycarbonyl, (C1-C7)- Haloalkyloxycarbonyl, (Ci-C7)-Alkoxy-(Ci-C7)-alkoxycarbonyl, (C2-C7)- Alkenyloxy-(Ci-C7)-alkoxycarbonyl, (Ci-C7)-Alkylamino-(Ci-C7)- alkoxycarbonyl, Tris[(CrC7)-alkyl]silyloxy-(Ci-C7)-alkoxycarbonyl, Bis[(Ci-C7)-Alkyl]amino-(Ci-C7)-alkoxycarbonyl, (Ci-C7)-Alkyl[(Ci-C7)- alkyl]amino-(Ci-C7)-alkoxycarbonyl, Cyano-(Ci-C7)-alkoxycarbonyl, Heterocyclyl-N-(Ci-C7)-alkoxycarbonyl, Heteroaryloxycarbonyl, (C3-C7) -cycloalkyl- (Ci-C7) alkylcarbonylamino, Heteroaryicarbonylamino, (CrC 7) alkoxy (Ci-C7) alkylcarbonylamino, hydroxy (CrC 7) - alkylcarbonylamino, (Ci-C 7 ) alkoxycarbonylamino (Ci-C7) - alkylcarbonylamino, cyano, cyano (-C 7) alkyl, hydroxycarbonyl, (dC 7) alkoxycarbonyl, (C3-C 7) cycloalkoxycarbonyl, (C3-C 7) cycloalkyl - (C 1 -C 7 ) -alkoxycarbonyl, aryloxycarbonyl, aryl- (C 1 -C 4 ) -alkoxycarbonyl, (C2-C-7) -alkenyloxycarbonyl, (C2-C-7) -alkynyloxycarbonyl, (C1-C7) -haloalkyloxycarbonyl, (Ci-C7) -alkoxy- (Ci-C7) -alkoxycarbonyl, (C2-C7) - Alkenyloxy- (Ci-C7) -alkoxycarbonyl, (Ci-C7) -alkylamino- (Ci-C7) -alkoxycarbonyl, tris [(CrC7) -alkyl] silyloxy- (Ci-C7) -alkoxycarbonyl, bis [(Ci-C 7) alkyl] amino- (Ci-C 7) alkoxycarbonyl, (Ci-C 7) alkyl [(Ci-C7) - alkyl] amino- (Ci-C7) alkoxycarbonyl, cyano (Ci-C7 ) -alkoxycarbonyl, heterocyclyl-N- (C 1 -C 7) -alkoxycarbonyl, heteroaryloxycarbonyl,
Heteroaryl-(Ci-C7)-alkoxycarbonyl, Heterocyclyl-(Ci-C7)-alkoxycarbonyl, Heterocyclyloxycarbonyl, (C2-C7)-Alkenyl-(Ci-C7)-alkoxycarbonyl, Heteroaryl- (C 1 -C 7) -alkoxycarbonyl, heterocyclyl- (C 1 -C 7) -alkoxycarbonyl, heterocyclyloxycarbonyl, (C 2 -C 7) -alkenyl- (C 1 -C 7) -alkoxycarbonyl,
(C2-C7)-Alkinyl-(Ci-C7)-alkoxycarbonyl, Aryl-(C2-C7)-alkinyloxycarbonyl, Aryl-(C2-C7)-alkenyloxycarbonyl, Aminocarbonyl, (C1-C7)- Alkylaminocarbonyl, Bis[(CrC7)-alkyl]aminocarbonyl, (C1-C7)- Alkyl[(Ci-C7)-Alkyl]aminocarbonyl, (Ci-C7)-Alkyl[(Ci-C7)- Alkoxyjaminocarbonyl, (C2-C7)-Alkenylaminocarbonyl, (C3-C7)- CycloalkylaminocarbonyL Arylaminocarbonyl, Aryl-(Ci-C7)- alkylaminocarbonyl, Heteroaryl-(Ci-C7)-alkylaminocarbonyl, Cyano- (CrC7)-alkylaminocarbonyl, (Ci-C7)-Haloalkylaminocarbonyl, (C2-C7)- Alkinyl-(Ci-C7)-alkylaminocarbonyl, (C1-C7)- Alkoxycarbonylaminocarbonyl, Aryl-(Ci-C7)- alkoxycarbonylaminocarbonyl, Hydroxycarbonyl-(Ci-C7)-alkyl, (C1-C7)- Alkoxycarbonyl-(d-C7)-alkyl, (C3-C7)-Cycloalkoxycarbonyl-(CrC7)-alkyl, (C3-C7)-Cycloalkyl-(Ci-C7)-alkoxycarbonyl-(Ci-C7)-alkyl, (C2-C7)- Alkenyloxycarbonyl-(d-C7)-alkyl, Aryl-(d-C7)-alkoxycarbonyl-(Ci-C7)- alkyl, (Ci-C7)-Alkylaminocarbonyl-(Ci-C7)-alkyl, Aminocarbonyl-(Ci-C7)- alkyl, Bis[(Ci-C7)-alkyl]aminocarbonyl-(Ci-C7)-alkyl, (C3-C7)- Cycloalkylaminocarbonyl-(CrC7)-alkyl, Aryl-(Ci-C7)-alkylaminocarbonyl- (Ci-C7)-alkyl, Heteroaryl-(Ci-C7)-alkylaminocarbonyl-(Ci-C7)-alkyl, Cyano-(Ci-C7)-alkylaminocarbonyl-(Ci-C7)-alkyl, (C1-C7)- Haloalkylaminocarbonyl-(Ci-C7)-alkyl, (C2-C7)-Alkinyl-(Ci-C7)- alkylaminocarbonyl-(Ci-C7)-alkyl, (C3-C7)-Cycloalkyl-(Ci-C7)- alky!aminocarbonyl-(CrC7)-alkyl, (CrC7)-Alkoxycarbonylaminocarbonyl- (d-C7)-alkyl, Aryl-(CrC7)-alkoxycarbonylaminocarbonyl-(Ci-C7)-alkyl, (CrC7)-Alkoxycarbonyl-(Ci-C7)-alkylaminocarbonyl, Hydroxycarbonyl- (Ci-C7)-alkylaminocarbonyl, Aryl-(Ci-C7)-alkoxycarbonyl-(CrC7)-
alkylaminocarbonyl, (Ci-C7)-Alkoxycarbonyl-heterocyclyl-N-carbonyl, (Ci- C7)-Alkoxycarbonyl-(Ci-C6)-alkyl-heterocyclyiidenaminocarbonyl, (C1-C7)- Alkoxycarbonylheterocyclyliden-(Ci-C6)-alkyiaminocarbonyl (C1-C7)-(C 2 -C 7) alkynyl (C 1 -C 7) alkoxycarbonyl, aryl- (C 2 -C 7) alkynyloxycarbonyl, aryl- (C 2 -C 7) alkenyloxycarbonyl, aminocarbonyl, (C 1 -C 7) -alkylaminocarbonyl, bis [(CrC 7 ) -alkyl] aminocarbonyl, (C 1 -C 7 ) -alkyl [(C 1 -C 7 ) -alkyl] aminocarbonyl, (C 1 -C 7 ) -alkyl [(C 1 -C 7 ) -alkoxy] aminocarbonyl, (C 2 -C 7 ) -alkenylaminocarbonyl , (C 3 -C 7) -cycloalkylaminocarbonyL arylaminocarbonyl, aryl- (C 1 -C 7) -alkylaminocarbonyl, heteroaryl- (C 1 -C 7) -alkylaminocarbonyl, cyano- (C 1 -C 7) -alkylaminocarbonyl, (C 1 -C 7) -haloalkylaminocarbonyl, (C 2 -C 7) ) - alkynyl- (C 1 -C 7) -alkylaminocarbonyl, (C 1 -C 7) -alkoxycarbonylaminocarbonyl, aryl- (C 1 -C 7) -alkoxycarbonylaminocarbonyl, hydroxycarbonyl- (C 1 -C 7) -alkyl, (C 1 -C 7) -alkoxycarbonyl- (i.e. -C 7 ) -alkyl, (C 3 -C 7 ) -cycloalkoxycarbonyl- (C 1 -C 7 ) -alkyl, (C 3 -C 7 ) -cycloalkyl- (C 1 -C 7 ) -alkoxycarbonyl- (C 1 -C 7 ) -alkyl, (C 2 -C 7 ) Alkenyloxycarbonyl- (C 1 -C 7) -alkyl, aryl- (C 1 -C 7) -alkoxycarbonyl- (C 1 -C 7) -alkyl, (C 1 -C 7) -alkylaminocarbonyl- (C 1 -C 7) -alkyl, aminocarbonyl- (C 1 -C 4) -alkyl C7) - alkyl, bis [(Ci-C7) alkyl] aminocarbonyl (Ci-C7) alkyl, (C 3 -C 7) -cycloalkylaminocarbonyl- (C 1 -C 7) -alkyl, aryl- (C 1 -C 7) -alkylaminocarbonyl- (C 1 -C 7) -alkyl, heteroaryl- (C 1 -C 7) -alkylaminocarbonyl- (C 1 -C 7) -alkyl, Cyano- (C 1 -C 7) -alkylaminocarbonyl- (C 1 -C 7 ) -alkyl, (C 1 -C 7) -haloalkylaminocarbonyl- (C 1 -C 7 ) -alkyl, (C 2 -C 7) -alkynyl- (C 1 -C 7 ) - alkylaminocarbonyl (C 1 -C 7 ) -alkyl, (C 3 -C 7 ) -cycloalkyl- (C 1 -C 7 ) -alkylaminocarbonyl- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkoxycarbonylaminocarbonyl- (C 1 -C 7 ) -alkyl , Aryl- (C 1 -C 7) alkoxycarbonylaminocarbonyl- (C 1 -C 7) -alkyl, (C 1 -C 7) -alkoxycarbonyl- (C 1 -C 7) -alkylaminocarbonyl, hydroxycarbonyl- (C 1 -C 7) -alkylaminocarbonyl, aryl- (C 1 -C 7) -alkoxycarbonyl - (CRC7) - alkylaminocarbonyl, (C 1 -C 7) -alkoxycarbonyl-heterocyclyl-N-carbonyl, (C 1 -C 7) -alkoxycarbonyl- (C 1 -C 6) -alkyl-heterocyclicideneaminocarbonyl, (C 1 -C 7) -alkoxycarbonylheterocyclylidene- (C 1 -C 6) -alkylamino-carbonyl ( C1-C7) -
Alkoxycarbonyl-(Ci-C7)-Alkyl((Ci-C7)-alkyl)aminocarbonyl! (C1-C7)- Alkoxycarbonyl-(C3-C7)-cycloalkylidenaminocarbonyl, Heterocyclyl-N- carbonyl, (Ci-C7)-Alkoxy-(Ci-C7)-alkylaminocarbonyl, Aminocarbonyl- (Ci-C7)-alkylaminocarbonyl, (CrC7)-Alkylaminocarbonyl-(Ci-C7)- alkylaminocarbonyl, (C3-C7)-Cycloalkylaminocarbonyl-(Ci-C7)- alkylaminocarbonyl, (C3-C7)-Cycloalkyl-(Ci-C7)-alkylaminocarbonyl, (C3-C7)-Cyc!oalkyl-(Ci-C7)-alkylaminocarbonyl-(Ci-C7)-alkyl, (C3-C7)- Cycloalkyl-(Ci-C7)-alkylaminocarbonyl-(Ci-C7)-alkylaminocarbonyl, (C2-C7)-A!kenyl-(Ci-C7)-alkylaminocarbonyl, (C2-C7)- Alkenylaminocarbonyl-(Ci-C7)-alkyl, (C2-C7)-Alkenyl-(Ci-C7)- alkylaminocarbonyl-(Ci-C7)-alkyl, (CrC7)-Alkylcarbonyl, (C3-C7)- Cycloalkylcarbony!, Arylcarbonyl, Formyl, Hydroxyiminomethyl, Alkoxycarbonyl- (C 1 -C 7 ) -alkyl ((C 1 -C 7 ) -alkyl) aminocarbonyl ! (C1-C7) - alkoxycarbonyl (C3-C 7) -cycloalkylidenaminocarbonyl, heterocyclyl-N-carbonyl, (Ci-C7) alkoxy (Ci-C 7) alkylaminocarbonyl, aminocarbonyl (Ci-C7) - alkylaminocarbonyl, (CrC 7) alkylaminocarbonyl (Ci-C7) - alkylaminocarbonyl, (C3-C 7) -Cycloalkylaminocarbonyl- (Ci-C7) - alkylaminocarbonyl, (C3-C7) -cycloalkyl- (Ci-C 7 ) -alkylaminocarbonyl, (C 3 -C 7) -cycloalkyl- (C 1 -C 7) -alkylaminocarbonyl- (C 1 -C 7) -alkyl, (C 3 -C 7) -cycloalkyl- (C 1 -C 7 ) -alkylaminocarbonyl- (Ci ! -C 7) alkylaminocarbonyl, (C2-C7) -A kenyl- (Ci-C 7) alkylaminocarbonyl, (C2-C7) - Alkenylaminocarbonyl- (Ci-C7) alkyl, (C2-C7) Alkenyl- (C 1 -C 7 ) -alkylaminocarbonyl- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkylcarbonyl, (C 3 -C 7 ) -cycloalkylcarbony !, arylcarbonyl, formyl, hydroxyiminomethyl,
Aminoiminomethyl, (Ci-C7)-Alkoxyiminomethyl, (C1-C7)- Alkylaminoiminomethyl, Bis[(Ci-C7)-alkyl]aminoiminomeihyl, (C3-C7)- Cycloalkoxyiminomethyl, (C3-C7)-Cycloalkyl-(Ci-C7)-alkoximinomethyl, Aryloximinomethyl, Aryl-(Ci-C7)-alkoxyiminomeihyl, Aryl-(Ci-C7)- alkylaminoiminomethyl, (C2-C7)-Alkenyloxyiminomeihyl, Aminoiminomethyl, (C 1 -C 7 ) -alkoxyiminomethyl, (C 1 -C 7 ) -alkylaminoiminomethyl, bis [(C 1 -C 7 ) -alkyl] aminoiminomethyl, (C 3 -C 7 ) -cycloalkoxyiminomethyl, (C 3 -C 7 ) -cycloalkyl- ( Ci-C 7) -alkoximinomethyl, Aryloximinomethyl, aryl (Ci-C 7) -alkoxyiminomeihyl, aryl (Ci-C7) - alkylaminoiminomethyl, (C2-C7) -Alkenyloxyiminomeihyl,
Arylaminoiminomethyl, Arylsulfonylaminoiminomethyl, Heteroaryl-(Ci-C7)- alkyl, Heterocyclyl-(Ci-C7)-alkyl, Hydroxycarbonylheterocyclyl, (C1-C7)- Alkoxycarbonylheterocyclyl, (C2-C7)-Alkenyloxycarbonylheterocyclyl, (C2-C7)-Alkenyl-(Ci-C7)-alkoxycarbonylheterocyclyl, Aryl-(Ci-C7)- alkoxycarbonylheterocyclyl, (C3-C7)-Cycloalkoxycarbonylheterocyclyl, (C3-C7)-Cycloalkyl-(Ci-C7)-alkoxycarbonylheierocyclyl, Arylaminoiminomethyl, Arylsulfonylaminoiminomethyl, heteroaryl (Ci-C7) - alkyl, heterocyclyl- (Ci-C7) alkyl, Hydroxycarbonylheterocyclyl, (C1-C7) - Alkoxycarbonylheterocyclyl, (C2-C7) -Alkenyloxycarbonylheterocyclyl, (C2-C7 ) -Alkenyl- (C 1 -C 7 ) -alkoxycarbonyl-heterocyclyl, aryl- (C 1 -C 7 ) -alkoxycarbonyl-heterocyclyl, (C 3 -C 7 ) -cycloalkoxycarbonyl-heterocyclyl, (C 3 -C 7 ) -cycloalkyl- (C 1 -C 7 ) -alkoxycarbonylheierocyclyl,
Aminocarbonylheterocyclyl, (Ci-C7)-Alkylaminocarbonylheterocyclyl, Bis[(Ci-C7)-Alkyl]aminocarbonylheterocyclyl, (C3-C7)- Cycloalkylaminocarbonylheterocyclyl, Aryl-(Ci-C7)- alkylaminocarbonylheterocyclyl, (C2-C7)-Aminocarbonylheterocyclyl, (C 1 -C 7 ) -alkylaminocarbonylheterocyclyl, bis [(C 1 -C 7 ) -alkyl] aminocarbonylheterocyclyl, (C 3 -C 7 ) -cycloalkylaminocarbonylheterocyclyl, aryl- (C 1 -C 7 ) -alkylaminocarbonylheterocyclyl, (C 2 -C 7 ) -
Alkenylaminocarbonylheterocyclyl, Hydroxycarbonylheterocyclyl-(Ci-C7)- alkyl, (Ci-C7)-Alkoxycarbonylheterocyclyl-(Ci-C7)-alkyl, Hydroxycarbonyl-Alkenylaminocarbonylheterocyclyl, Hydroxycarbonylheterocyclyl- (Ci-C7) - alkyl, (Ci-C 7) -Alkoxycarbonylheterocyclyl- (Ci-C 7) alkyl, hydroxycarbonyl
(C3-C7)-cycloalkyl-(Ci-C7)-alkyl, (Ci-C7)-Alkoxycarbonyl-(C3-C7)- cycloalkyl-(Ci-C7)-alkyl, Hydroxyaminocarbonyl, (C1-C7)-
Alkoxyaminocarbonyl, Aryl-(Ci-C7)-alkoxyaminocarbonyl, Heterocyclyl, (Ci-C7)-Alkylcarbonyloxy, Arylcarbonyloxy, Heteroarylcarbonyloxy, (C3-C7)-Cycloalkylcarbonyloxy, (Ci-C7)-Alkoxycarbonyloxy, (C2-C7)- Alkenyloxycarbonyloxy steht, (C3-C7) cycloalkyl- (Ci-C7) alkyl, (Ci-C 7) alkoxycarbonyl (C 3 -C 7) - cycloalkyl- (Ci-C7) alkyl, hydroxyaminocarbonyl, (C1 C7) - Alkoxyaminocarbonyl, aryl- (C 1 -C 7) alkoxyaminocarbonyl, heterocyclyl, (C 1 -C 7) -alkylcarbonyloxy, arylcarbonyloxy, heteroarylcarbonyloxy, (C 3 -C 7) -cycloalkylcarbonyloxy, (C 1 -C 7) -alkoxycarbonyloxy, (C 2 -C 7) -alkenyloxycarbonyloxy .
R7, R8 , R9 und R1Ü unabhängig voneinander für Wasserstoff, Halogen, Nitro,R 7 , R 8 , R 9 and R 1Ü independently of one another represent hydrogen, halogen, nitro,
Amino, Cyano, (Ci-C7)-Alkyl, Aryl, Heteroaryl, (C3-C7)-Cycloalkyl, (C4-C7)- Cycloalkenyl. (C2-C7)-Alkenyl, (C2-C7)-Alkinyl, (C2-C7)-Alkenyl-(Ci-C7)- alkyl, (C2-C7)-Alkinyl-(Ci-C7)-alkyl. Hydroxy, (Ci-C7)-Alkoxy, (C1-C7)- Alkoxy-(Ci-C7)-alkoxy, (Ci-C7)-Alkoxy-(Ci-C7)-alkyl, Hydroxy-(Ci-C7)- alkyl, (Ci-C7)-Haloalkoxy, (Ci-C7)-Haloalkyl, (C2-C7)-Haloalkenyl, (C2-C7)- Haloalkinyl, (Ci-C7)-Haloalkoxy-(Ci-C7)-alkyl, (Ci-C7)-Alkoxy-(Ci-C7)- haloalkyl, (Ci-C7)-Haloalkoxy-(Ci-C7)-haloalkyl, Hydrothio, (C1-C7)- Alkylthio, (CrC7)-Haloalkylthio, (Ci-C7)-Alkylthio-(Ci-C7)-alkyl, (C1-C7)- Haloalkylthio-(Ci-C7)-alkyl, (Ci-C7)-Alkylamino, Bis[(Ci-C7)-alkyl]amino, (C2-C7)-Alkenylamino, (C3-C7)-Cycloalkylamino, (C1-C7)- Alkylcarbonylamino, (C3-C7)-Cycloalkylcarbonylamino, Amino, cyano, (C 1 -C 7 ) -alkyl, aryl, heteroaryl, (C 3 -C 7 ) -cycloalkyl, (C 4 -C 7 ) -cycloalkenyl. (C 2 -C 7) alkenyl, (C 2 -C 7) -alkynyl, (C2-C7) alkenyl (Ci-C7) - alkyl, (C2-C7) alkynyl (Ci- C7) alkyl. Hydroxy, (C 1 -C 7 ) -alkoxy, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkoxy, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, hydroxy- (C 1 -C 4 ) -alkyl C 7) - alkyl, (Ci-C7) haloalkoxy, (Ci-C7) haloalkyl, (C 2 -C 7) haloalkenyl, (C2-C7) - haloalkynyl, (Ci-C7) haloalkoxy - (Ci-C7) alkyl, (Ci-C7) alkoxy (Ci-C7) - haloalkyl, (Ci-C7) haloalkoxy (Ci-C7) haloalkyl, Hydrothio, (C1- C7) - alkylthio, (C 1 -C 7 ) -haloalkylthio, (C 1 -C 7 ) -alkylthio (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -haloalkylthio (C 1 -C 7 ) -alkyl, (C 1 -C-C) 7 ) -alkylamino, bis [(C 1 -C 7 ) -alkyl] amino, (C 2 -C 7 ) -alkenylamino, (C 3 -C 7 ) -cycloalkylamino, (C 1 -C 7 ) -alkylcarbonylamino, (C 3 -C 7 ) -cycloalkylcarbonylamino,
Arylcarbonylamino, Heteroarylcarbonylamino, Formylamino, (C1-C7)- Haloalkylcarbonylamino, (Ci-C7)-Alkoxycarbonylamino, (C1-C7)- Alkylaminocarbonylamino, (Ci-C7)-Alkyl[(Ci-C7)- Alkyljaminocarbonylamino, (Ci-C7)-Alkylsulfonylamino, (C3-C7)- Cycloalkylsulfonylamino, Arylsulfonylamino, Hetarylsulfonylamino, Sulfonyl-(CrC7)-haloalkylamino, Amino-(Ci-C7)-alkylsulfonyl, Amino- (Ci-C7)-haloalkylsulfonyl, (Ci-C7)-Alkylaminosulfonyl, Bis[(CrC7)- alkyljaminosulfonyl, (C3-C7)-Cycloalkylaminosulfonyl, (C1-C7)- Haloalkylaminosulfonyl, Heteroarylaminosulfonyl, Arylaminosulfonyl, Aryl- (Ci-C7)-alkylaminosulfonyl, (Ci-C7)-Alkylsulfonyl, (C3-C7)- Cycloalkylsulfonyl, Arylsulfonyl, Hydroxycarbonyl, (C1-C7)- Alkoxycarbonyl, (C3-C7)-Cycloalkoxycarbonyl, (C3-C7)-Cycloalkyl-(Ci-C7)- alkoxycarbonyl, Aryloxycarbonyl, Aryl-(CrC7)-alkoxycarbonyl, (C2-C7)- Alkenyloxycarbonyl, (C2-C7)-Alkinyloxycarbonyl, Aminocarbonyl, (C1-C7)- Alkylaminocarbonyl, Bis[(Ci-C7)-alkyl]aminocarbonyl, (C1-C7)- Alkyl[(Ci-C7)-Alkyl]aminocarbonyl, (Ci-C7)-Alkyl[(Ci-C7)- Alkoxy]aminocarbonyl, (C2-C7)-Alkenylaminocarbonyl, (C3-C7)-
Cycloalkylaminocarbonyl, Arylaminocarbonyl, Aryl-(Ci-C-7)- alkylaminocarbonyl stehen, Arylcarbonylamino, heteroarylcarbonylamino, formylamino, (C 1 -C 7) -haloalkylcarbonylamino, (C 1 -C 7) -alkoxycarbonylamino, (C 1 -C 7) -alkylaminocarbonylamino, (C 1 -C 7) -alkyl [(C 1 -C 7) -alkylaminocarbonylamino, (C 1 -C 7) ) Alkylsulfonylamino, (C 3 -C 7 ) -cycloalkylsulfonylamino, arylsulfonylamino, hetarylsulfonylamino, sulfonyl- (C 1 -C 7) -haloalkylamino, amino- (C 1 -C 7 ) -alkylsulfonyl, amino- (C 1 -C 7 ) -haloalkylsulfonyl, (C 1 -C 7 ) -Alkylaminosulfonyl, bis [(CrC 7 ) -alkylaminosulfonyl, (C 3 -C 7 ) -cycloalkylaminosulfonyl, (C 1 -C 7 ) -haloalkylaminosulfonyl, heteroarylaminosulfonyl, arylaminosulfonyl, aryl- (C 1 -C 7 ) -alkylaminosulfonyl, (C 1 -C 7 ) Alkylsulfonyl, (C3-C7) cycloalkylsulfonyl, arylsulfonyl, hydroxycarbonyl, (C1-C7) -alkoxycarbonyl, (C3-C7) -cycloalkoxycarbonyl, (C3-C7) -cycloalkyl- (Ci-C7) -alkoxycarbonyl, aryloxycarbonyl, aryl - (C 1 -C 7) alkoxycarbonyl, (C 2 -C 7) alkenyloxycarbonyl, (C 2 -C 7) alkynyloxycarbonyl, aminocarbonyl, (C 1 -C 7) -alkylaminocarbonyl, bis [(C 1 -C 7) -alkyl] aminocarbonyl, (C 1 -C 7) - alkyl [(Ci-C 7 ) - Alkyl] aminocarbonyl, (C 1 -C 7 ) -alkyl [(C 1 -C 7 ) -alkoxy] -aminocarbonyl, (C 2 -C 7 ) -alkenylaminocarbonyl, (C 3 -C 7 ) - Cycloalkylaminocarbonyl, arylaminocarbonyl, aryl- (Ci-C-7) -alkylaminocarbonyl,
A1, A2, A3 und A4 gleich oder verschieden sind und unabhängig voneinander fürA 1 , A 2 , A 3 and A 4 are the same or different and are each independently
N (Stickstoff) oder die Gruppierungen C-H, C-CH3, C-F, C-Cl, C-Br, C-l, C-OCF3, C-OCH3, C-CF3, C-CO2H, C-CO2CH3 stehen, wobei jedoch in keinem Fall mehr als zwei -Atome benachbart sind, N (nitrogen) or the groupings CH, C-CH 3, are CF, C-Cl, C-Br, CI, C-OCF3, C-OCH3, C-CF 3, C-CO2H, C-CO2CH3, but using in no case are more than two atoms adjacent,
R11 und R12 unabhängig voneinander für Wasserstoff, Halogen, (Ci-C7)-Alkyl, Aryl, Heteroaryl, Heterocyclyl, (C3-C7)-Cycloalkyl, (C2-C7)-Alkenyl, (C2-C7)-Alkinyl, (Ci-C7)-Alkoxy, (Ci-C7)-Alkoxy-(Ci-C7)-alkyl, Aryloxy- (Ci-C7)-alkyl, (CrC7)-Haloalkoxy, (Ci-C7)-Haloalkyl, (Ci-C7)-Haloalkoxy- (CrC7)-alkyl, (Ci-C7)-Alkoxy-(Ci-C7)-haloalkyl, (Ci-C7)-Haloalkoxy- (CrC7)-haloalkyl, (Ci-C7)-Alkylthio, (Ci-C7)-Haloalkylthio, (C1-C7)- Alkylthio-(Ci-C7)-alkyl, Hydroxycarbonyl, (d-C^-Alkoxycarbonyl, (C3-C7)- Cycloalkoxycarbonyl, (C3-C7)-Cycloalkyl-(Ci-C7)-alkoxycarbonyl, R 11 and R 12 independently of one another represent hydrogen, halogen, (C 1 -C 7 ) -alkyl, aryl, heteroaryl, heterocyclyl, (C 3 -C 7 ) -cycloalkyl, (C 2 -C 7 ) -alkenyl, (C 2 -C 7 ) - Alkynyl, (C 1 -C 7 ) -alkoxy, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, aryloxy- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -haloalkoxy, C 7 ) -haloalkyl, (C 1 -C 7 ) -haloalkoxy- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -haloalkoxy ( -C 7) haloalkyl, (Ci-C7) -alkylthio, (Ci-C 7) haloalkylthio, (C1-C7) - alkylthio (Ci-C7) alkyl, hydroxycarbonyl, (dC ^ alkoxycarbonyl, (C3 -C7) - cycloalkoxycarbonyl, (C3-C7) -cycloalkyl- (Ci-C7) -alkoxycarbonyl,
Aryloxycarbonyl, Aryl-(CrC7)-alkoxycarbonyl, (C2-C7)- Alkenyloxycarbonyl, (C2-C7)-Alkinyloxycarbonyl, Aminocarbonyl, (C1-C7)- Alkylaminocarbonyl, Bis[(Ci-C7)-alkyl]aminocarbonyl, (C1-C7)- Alkyl[(Ci-C7)-Alkyl]aminocarbonyl, (Ci-C7)-Alkyl[(Ci-C7)- Alkoxyjaminocarbonyl, (C2-C7)-Alkenylaminocarbonyl, (C3-C7)- Cycloalkylaminocarbonyl, Arylaminocarbonyl, Aryl-(d-C7)- alkylaminocarbonyl stehen, Aryloxycarbonyl, aryl- (C 1 -C 7) -alkoxycarbonyl, (C 2 -C 7) -alkenyloxycarbonyl, (C 2 -C 7) -alkynyloxycarbonyl, aminocarbonyl, (C 1 -C 7) -alkylaminocarbonyl, bis [(C 1 -C 7) -alkyl] -aminocarbonyl, (Cl C7) - alkyl [(Ci-C 7) alkyl] aminocarbonyl, (Ci-C7) alkyl, [(Ci-C 7) - Alkoxyjaminocarbonyl, (C2-C7) -Alkenylaminocarbonyl, (C3-C7) - cycloalkylaminocarbonyl, Arylaminocarbonyl, aryl- (C 1 -C 7) -alkylaminocarbonyl,
A5 für S (Schwefel), O (Sauerstoff) oder die Gruppierungen N-H, N-CH3, N- CH2CH3, N-CH(CH3)2, N-C02t-Bu, N-Aryl, N-Heteroaryl, N-Heterocyclyl steht, A 5 represents S (sulfur), O (oxygen) or the groupings NH, N-CH 3 , N-CH 2 CH 3 , N-CH (CH 3 ) 2 , N-CO 2 t-Bu, N-aryl, N-heteroaryl, N-heterocyclyl is
R13, R14, R17 und R18 unabhängig voneinander für Wasserstoff, (Ci-C7)-Alkyl, Halogen, (C3-C7)-Cycloalkyl, Aryl, Heteroaryl, Heterocyclyl, (C2-C7)- Alkenyl, (C2-C7)-Alkenyl-(Ci-C7)-alkyl, Aryl-(Ci-C7)-alkyl, (CrC7)-Alkoxy,R 13 , R 14 , R 17 and R 18 independently of one another represent hydrogen, (C 1 -C 7) -alkyl, halogen, (C 3 -C 7) -cycloalkyl, aryl, heteroaryl, heterocyclyl, (C 2 -C 7) -alkenyl, (C 2 -C 4) -alkyl -C 7) alkenyl (Ci-C7) alkyl, aryl (Ci-C7) alkyl, (CrC 7) alkoxy,
(Ci-C7)-Alkoxy-(Ci-C7)-alkoxy, (Ci-C7)-Alkoxy-(Ci-C7)-alkyl, Hydroxy, (Ci-C7)-Haloalkyl, (Ci-C7)-Haloalkylthio stehen oder
R13 und R17 mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls weiter substituierten 5 bis 7-gliedrigen Ring bilden, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkoxy, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, hydroxy, (C 1 -C 7 ) -haloalkyl, C 7 ) haloalkylthio or R 13 and R 17 with the atoms to which they are attached form a completely saturated or partially saturated, optionally further substituted 5 to 7-membered ring,
A6, A7 gleich oder verschieden sind und unabhängig voneinander für O A 6 , A 7 are the same or different and are each independently O.
(Sauerstoff), S (Schwefel). N-H, N-OCH3, N-CH3 oder die Gruppierung CR15R16 stehen, wobei jedoch in keinem Fall zwei N-, O- oder S-Atome benachbart sind, und wobei R15 und R16 in der Gruppierung CR15R16 jeweils gleiche oder verschiedene Bedeutungen gemäß der (Oxygen), S (sulfur). NH, N-OCH 3 , N-CH 3 or the group CR 15 R 16 are, but in any case, two N, O or S atoms are adjacent, and wherein R 15 and R 16 in the grouping CR 15 R 16 each have the same or different meanings according to the
nachstehenden Definition haben und have the following definition and
R15 und R16 unabhängig voneinander für Wasserstoff, Halogen, (Ci-C7)-Alkyl, Aryl, Heteroaryl, Heterocyclyl, (C3-C7)-Cycloalkyl, (C2-C7)-Alkenyl, R 15 and R 16 independently of one another represent hydrogen, halogen, (C 1 -C 7 ) -alkyl, aryl, heteroaryl, heterocyclyl, (C 3 -C 7 ) -cycloalkyl, (C 2 -C 7 ) -alkenyl,
(Ci-C7)-Alkoxy, (Ci-C7)-Alkoxy-(d-C7)-alkyl, Aryloxy-(d-C7)-alkyl, (C 1 -C 7 ) -alkoxy, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, aryloxy- (C 1 -C 7 ) -alkyl,
(Ci-C7)-Haloalkoxy, (Ci-C7)-Haloalkyl, (CrC7)-Haloalkoxy(Ci-C7)-alkyl, (Ci-C7)-Alkoxy-(d-C7)-haloalkyl, (Ci-C7)-Haloalkoxy-(CrC7)-haloalkyl, (d-C7)-Alkylthio, (d-C7)-Haloalkylthio, (Ci-C7)-Alkylthio-(CrC7)-alkyl, Hydroxycarbonyl, (Ci-C7)-Alkoxycarbonyl, (C3-C )-Cycloalkoxycarbonyl, (C3-C7)-Cycloalkyl-(Ci-C7)-alkoxycarbonyl, Aryloxycarbonyl, Aryl-(Ci-C7)- alkoxycarbonyl , (C2-C7)-Alkenyloxycarbonyl , (C2-C7)-Al ki nyloxycarbonyl , Aminocarbonyl, (Ci-C7)-Alkylaminocarbonyl, Bis[(d-C7)- alkyljaminocarbonyl, (Ci-C7)-Alkyl[(Ci-C7)-Alkyl]aminocarbonyl, (Ci-C7)- Alkyl[(d-C7)-Alkoxy]aminocarbonyl, (C2-C7)-Alkenylaminocarbonyl, (C3-C7)-Cycloalkylaminocarbonyl, Arylaminocarbonyl, Aryl-(Ci-C7)- alkylaminocarbonyl, Amino, (Ci-C7)-Alkylamino, (C:rC7)-Cycloalkylamino, Bis-[(Ci-C7)-Alkyl]amino stehen, (Ci-C7) haloalkoxy, (Ci-C7) haloalkyl, (CrC 7) haloalkoxy (Ci-C7) alkyl, (Ci-C7) alkoxy (dC 7) -haloalkyl, ( Ci-C7) haloalkoxy (-C 7) haloalkyl, (dC 7) alkylthio, (dC 7) haloalkylthio, (Ci-C7) -alkylthio (-C 7) alkyl, hydroxycarbonyl, (Ci- C 7) alkoxycarbonyl, (C3-C) -cycloalkoxycarbonyl, (C3-C7) -cycloalkyl- (Ci-C 7) alkoxycarbonyl, aryloxycarbonyl, aryl- (Ci-C7) - alkoxycarbonyl, (C2-C7 ) Alkenyloxycarbonyl, (C 2 -C 7 ) -alkyloxycarbonyl, aminocarbonyl, (C 1 -C 7 ) -alkylaminocarbonyl, bis [(C 1 -C 7 ) -alkylaminocarbonyl, (C 1 -C 7 ) -alkyl [(C 1 -C 7 ) Alkyl] aminocarbonyl, (Ci-C 7 ) - alkyl [(dC 7 ) alkoxy] aminocarbonyl, (C 2 -C 7 ) alkenylaminocarbonyl, (C 3 -C 7 ) -cycloalkylaminocarbonyl, arylaminocarbonyl, aryl- (Ci-C 7 ) - alkylaminocarbonyl, amino, (Ci-C 7 ) -alkylamino, (C: rC 7 ) -cycloalkylamino, bis - [(Ci-C 7 ) -alkyl] amino,
R19, R20, R22 und R23 unabhängig voneinander für Wasserstoff, (Ci-C7)-Alkyl, Halogen, (C3-C7)-Cycloalkyl, Aryl, Heteroaryl, Heterocyclyl, (C2-C7)- Alkenyl, Aryl-(d-C7)-alkyl, (Ci-C7)-Alkoxy, (Ci-C7)-Alkoxy-(Ci-C7)-alkoxy, (Ci-C7)-Alkoxy-(Ci-C7)-alkyl, (d-C7)-Haloalkyl stehen,
A8 für O (Sauerstoff), S (Schwefel), N-H, N-CH3, N-OCH3 oder die Gruppierung CHR21 steht und wobei R21 in der Gruppierung CHR21 die Bedeutung gemäß der nachstehenden Definition hat, R 19 , R 20 , R 22 and R 23 independently of one another represent hydrogen, (C 1 -C 7 ) -alkyl, halogen, (C 3 -C 7 ) -cycloalkyl, aryl, heteroaryl, heterocyclyl, (C 2 -C 7 ) -alkenyl, aryl (dC 7) alkyl, (Ci-C7) alkoxy, (Ci-C7) alkoxy (Ci-C7) alkoxy, (Ci-C7) alkoxy (Ci-C 7 ) -alkyl, (dC 7 ) -haloalkyl, A 8 is O (oxygen), S (sulfur), NH, N-CH 3 , N-OCH 3 or the moiety CHR 21 , and wherein R 21 in the moiety CHR 21 has the meaning as defined below,
R21 für Wasserstoff, Halogen, (Ci-C7)-Alkyl, Aryl, Heteroaryl, Heterocyciyl, R 21 represents hydrogen, halogen, (C 1 -C 7) -alkyl, aryl, heteroaryl, heterocyciyl,
(C3-C7)-Cycloalkyl, (C2-C7)-Alkenyl, (d-C7)-Alkoxy, (Ci-C7)-Alkoxy- (Ci-C7)-alkyl, Aryloxy-(d-C7)-alkyl, (Ci-C7)-Haloalkoxy, (CrC7)-Haloalkyl, (Ci-C7)-Alkoxy-(Ci-C7)-haloalkyl, (Ci-C7)-Haloalkoxy-(Ci-C7)-haloalkyl, (Ci-C7)-Alkylthio, (Ci-C7)-Haloalkylthio. (Ci-C7)-Alkylthio-(Ci-C7)-alkyl, Hydroxycarbonyl, (Ci-C7)-Alkoxycarbonyl, (C3-C7)-Cycloalkoxycarbonyl, Aryl-(Ci-C7)-alkoxycarbonyl, (C2-C7)-Alkenyloxycarbonyl, (C2-C7)- Alkinyloxycarbonyl, Aminocarbonyl, (Ci-C7)-Alkylaminocarbonyl, (C 3 -C 7) cycloalkyl, (C 2 -C 7) alkenyl, (dC 7) alkoxy, (Ci-C7) alkoxy (Ci-C7) alkyl, aryloxy (dC 7 ) -alkyl, (C 1 -C 7 ) -haloalkoxy, (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -haloalkoxy- (ci) C 7 ) haloalkyl, (C 1 -C 7 ) -alkylthio, (C 1 -C 7 ) -haloalkylthio. (C 1 -C 7 ) -alkylthio (C 1 -C 7 ) -alkyl, hydroxycarbonyl, (C 1 -C 7 ) -alkoxycarbonyl, (C 3 -C 7 ) -cycloalkoxycarbonyl, aryl- (C 1 -C 7 ) -alkoxycarbonyl, ( C 2 -C 7 -alkenyloxycarbonyl, (C 2 -C 7 ) -alkynyloxycarbonyl, aminocarbonyl, (C 1 -C 7 ) -alkylaminocarbonyl,
Bis[(Ci-C7)-alkyl]aminocarbonyl. (Ci-C7)-Alkyl[(Ci-C7)- Alkyljaminocarbonyl, (Ci-C7)-Alkyl[(Ci-C7)-Alkoxy]aminocarbonyl, Bis [(Ci-C 7 ) alkyl] aminocarbonyl. (Ci-C 7) alkyl [(Ci-C 7) - Alkyljaminocarbonyl, (Ci-C 7) alkyl [(Ci-C7) alkoxy] aminocarbonyl,
(C2-C7)-Alkenylaminocarbonyl, (C3-C7)-Cycloalkylaminocarbonyl, (C 2 -C 7 ) -alkenylaminocarbonyl, (C 3 -C 7 ) -cycloalkylaminocarbonyl,
Arylaminocarbonyl, Aryl-(Ci-C7)-alkylaminocarbonyl, Amino, (C1-C7)- Alkylamino, (C3-C7)-Cycloalkylamino, Bis[(CrC7)-Alkyl]amino steht, Arylaminocarbonyl, aryl- (C 1 -C 7 ) -alkylaminocarbonyl, amino, (C 1 -C 7 ) -alkylamino, (C 3 -C 7 ) -cycloalkylamino, bis [(C 1 -C 7 ) -alkyl] -amino,
R24, R25, R26, R28, R29 und R30 unabhängig voneinander für Wasserstoff, (C1-C7)- Alkyl, Halogen, (C3-C7)-Cycloalkyl, Aryl, Heteroaryl, Heterocyciyl, (C2-C7)- Alkenyl, (Ci-C7)-Alkoxy, (Ci-C7)-Alkoxy-(Ci-C7)-alkoxy, (d-C7)-Alkoxy- (Ci-C7)-alkyl, (Ci-C7)-Haloalkyl, (d-C7)-Alkylthio, (C,-C7)-Haloalkylthio stehen, R 24 , R 25 , R 26 , R 28 , R 29 and R 30 independently of one another are hydrogen, (C 1 -C 7 ) -alkyl, halogen, (C 3 -C 7 ) -cycloalkyl, aryl, heteroaryl, heterocyciyl, (C 2 -C 7 ) C7) - alkenyl, (C 1 -C 7 ) -alkoxy, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkoxy, (C 1 -C 4 ) -alkoxy- (C 1 -C 7 ) -alkyl, (Ci -C 7) haloalkyl, (dC 7) alkylthio, (C, -C 7) haloalkylthio stand,
A9 für O (Sauerstoff), S (Schwefel), N-H, N-CH3, N-OCH3 oder die Gruppierung CHR27 steht und wobei R27 in der Gruppierung CHR27 die Bedeutung gemäß der nachstehenden Definition hat und A 9 is O (oxygen), S (sulfur), NH, N-CH 3 , N -OCH 3 or the moiety CHR 27 and wherein R 27 in the moiety CHR 27 has the meaning as defined below and
R27 für Wasserstoff, Halogen, (Ci-C7)-Alkyl, Aryl, Heteroaryl, Heterocyciyl, R 27 represents hydrogen, halogen, (C 1 -C 7 ) -alkyl, aryl, heteroaryl, heterocyciyl,
(C3-C7)-Cycloalkyl, (C2-C7)-Alkenyl, (d-C7)-Alkoxy, (Ci-C7)-Alkoxy- (Ci-C7)-alkyl, Aryloxy-(CrC7)-alkyl, (Ci-C7)-Haloalkoxy, (Ci-C7)-Haloalkyl, (d-C7)-Alkylthio, (d-C7)-Haloalkylthio, Hydroxycarbonyl, (C1-C7)- Alkoxycarbonyl, (C3-C7)-Cycloalkoxycarbonyl, Aryl-(d-C7)- alkoxycarbonyl , (C2-C7)-Alkenyloxycarbonyl , (C2-C7)-Al ki nyloxycarbonyl ,
Aminocarbonyl, (Ci-C7)-Alkylaminocarbonyl, Bis[(Ci-C7)- alkyljaminocarbonyl, (Ci-C7)-Alkyl[(CrC7)-Alkyl]aminocarbonyl, (C1-C7)- Alkyl[(Ci-C7)-Alkoxy]aminocarbonyl, (C2-C7)-Alkenylaminocarbonyl, (C 3 -C 7) cycloalkyl, (C 2 -C 7) alkenyl, (dC 7) alkoxy, (Ci-C7) alkoxy (Ci-C7) alkyl, aryloxy- (CrC 7 ) -alkyl, (C 1 -C 7 ) -haloalkoxy, (C 1 -C 7 ) -haloalkyl, (C 1 -C 4 ) -alkylthio, (C 1 -C 4 ) -haloalkylthio, hydroxycarbonyl, (C 1 -C 7 ) -alkoxycarbonyl, (C 3 -C 4 ) 7) cycloalkoxycarbonyl, aryl (dC 7) - alkoxycarbonyl, (C 2 -C 7) alkenyloxycarbonyl, (C2-C7) -Al ki nyloxycarbonyl, Aminocarbonyl, (C 1 -C 7) -alkylaminocarbonyl, bis [(C 1 -C 7) -alkylaminocarbonyl, (C 1 -C 7) -alkyl [(C 1 -C 7) -alkyl] aminocarbonyl, (C 1 -C 7) -alkyl [(C 1 -C 7 ) Alkoxy] aminocarbonyl, (C 2 -C 7) alkenylaminocarbonyl,
(C3-C7)-Cycloalkylaminocarbonyl, Arylaminocarbonyl, Aryl-(CrC7)- alkylaminocarbonyl, Amino, (Ci-C7)-Alkylamino, (C3-C7)-Cycloalkylamino, Bis[(Ci-C7)-Alkyl]amino steht. (C 3 -C 7 ) -cycloalkylaminocarbonyl, arylaminocarbonyl, aryl- (C 1 -C 7 ) -alkylaminocarbonyl, amino, (C 1 -C 7 ) -alkylamino, (C 3 -C 7 ) -cycloalkylamino, bis [(C 1 -C 7 ) -alkyl] -amino stands.
Behandlung von Pflanzen, umfassend die Applikation einer zur Steigerung der Widerstandsfähigkeit von Pflanzen gegenüber abioti sehen Stressfaktoren wirksamen, nicht-toxischen Menge einer oder mehrerer der Verbindungen der Formel (I), oder jeweils deren Salze gemäß einem der Ansprüche 1 bis 3. Treatment of plants, comprising the application of a non-toxic amount of one or more of the compounds of the formula (I) which is effective for increasing the resistance of plants to abiotic stress factors, or in each case their salts according to one of Claims 1 to 3.
Behandlung gemäß Anspruch 4, wobei die abioti sehen Stressbedingungen einer oder mehrerer Bedingungen ausgewählt aus der Gruppe bestehend aus Dürre, Kältestress, Hitzestress, Trockenstress, osmotischem Stress, Staunässe, erhöhtem Bodensalzgehalt, erhöhtem Ausgesetztsein an Mineralien, The treatment of claim 4, wherein the abioti stress conditions include one or more conditions selected from the group consisting of drought, cold stress, heat stress, drought stress, osmotic stress, waterlogging, increased soil salt content, increased exposure to minerals,
Ozonbedingungen, Starklichtbedingungen, beschränkter Verfügbarkeit von Stickstoff n ä h rstoffe n und beschränkter Verfügbarkeit von Phosphornährstoffen entsprechen. Ozone conditions, high light conditions, limited availability of nitrogenous nutrients and limited availability of phosphorus nutrients.
Verwendung einer oder mehrerer Verbindungen der Formel (I), oder jeweils deren Salze gemäß einem der Ansprüche 1 bis 3 in der Sprühapplikation auf Pflanzen und Pflanzenteilen in Kombinationen mit einem oder mehrer Use of one or more compounds of the formula (I), or in each case their salts according to one of Claims 1 to 3, in the spray application to plants and plant parts in combinations with one or more
Wirkstoffen ausgewählt aud der Gruppe der Insektizide, Lockstoffe, Akarizide, Fungizide, Nematizide, Herbizide, wachstumsregulatorische Stoffe, Safener, die Pflanzen reife beeinflussende Stoffe und Bakterizide. Active ingredients selected from the group of insecticides, attractants, acaricides, fungicides, nematicides, herbicides, growth regulators, safeners, the plants mature affecting substances and bactericides.
Verwendung einer oder mehrerer Verbindungen der Formel (I), oder jeweils deren Salze gemäß einem der Ansprüche 1 bis 3 in der Sprühapplikation auf Pflanzen und Pflanzenteilen in Kombinationen mit Düngemitteln. Use of one or more compounds of the formula (I), or in each case their salts according to one of Claims 1 to 3, in the spray application on plants and plant parts in combinations with fertilizers.
Verwendung einer oder mehrerer Verbindungen der Formel (I), oder jeweils deren Salze gemäß einem der Ansprüche 1 bis 3 zur Applikation auf Use of one or more compounds of the formula (I), or in each case their salts according to one of Claims 1 to 3 for application
gentechnisch veränderten Sorten, deren Saatgut, oder auf Anbauflächen auf denen diese Sorten wachsen.
Verwendung von Sprühlösungen, die eine oder mehrere der Verbindungen der Formel (I), oder jeweils deren Salze gemäß einem der Ansprüche 1 bis 3 enthalten, zur Steigerung der Widerstandsfähigkeit von Pflanzen gegenüber abiotischen Stressfaktoren. genetically modified varieties, their seed, or on arable land on which these varieties grow. Use of spray solutions which comprise one or more of the compounds of the formula (I), or in each case their salts according to one of Claims 1 to 3, for increasing the resistance of plants to abiotic stress factors.
Verfahren zur Erhöhung der Stresstoleranz bei Pflanzen ausgewählt aus der Gruppe der Nutzpflanzen, Zierpflanzen, Rasenarten, oder Bäumen, dadurch gekennzeichnet, dass die Applikation einer ausreichenden, nicht-toxischen Menge einer oder mehrere Verbindungen der Formel (I), oder jeweils deren Salze gemäß einem der Ansprüche 1 bis 3 auf die Fläche, wo die entsprechende Wirkung gewünscht wird, umfassend die Anwendung auf die Pflanzen, deren Saatgut oder auf die Fläche auf der die Pflanzen wachsen, erfolgt. A method for increasing the stress tolerance in plants selected from the group of useful plants, ornamental plants, lawn species, or trees, characterized in that the application of a sufficient, non-toxic amount of one or more compounds of the formula (I), or respectively their salts according to a of claims 1 to 3 on the area where the corresponding effect is desired, comprising the application to the plants whose seeds or on the surface on which the plants grow takes place.
Verfahren gemäß Anspruch 10, wobei die Widerstandsfähigkeit der so behandelten Pflanzen gegenüber abiotischem Stress gegenüber nicht behandelten Pflanzen unter ansonsten gleichen physiologischen Bedingungen um mindestens 3% erhöht ist. A method according to claim 10, wherein the resistance of the thus treated plants to abiotic stress is increased by at least 3% over untreated plants under otherwise identical physiological conditions.
Substituierte 1 -(Arylethinyl)-, 1 -(Heteroarylethinyl)-, l-(Heterocyclylethinyl)- und 1 -(Cyloalkenylethinyl)-cyclohexanole der allgemeinen Formel (I), oder deren Salze Substituted 1- (arylethynyl) -, 1- (heteroarylethynyl) -, 1- (heterocyclylethynyl) - and 1- (cycloalkenylethynyl) -cyclohexanols of the general formula (I), or salts thereof
worin
[X-Y] für die Gruppierung wherein [XY] for the grouping
[x-YT steht, [x-YT stands,
Q für die Gruppierungen Q-1 bis Q-6 Q for the groupings Q-1 to Q-6
steht, wobei R7, R8, R9, R10, R11, R12, R13, R14, R17, R18, R19, R20, R22, R23, R24, R25, R26, R28, R29 und R30 und A1 bis A9 jeweils die Bedeutung gemäß der nachstehenden Definitionen haben und wobei der Pfeil für eine Bindung zur jeweiligen Gruppierung C-R6 in der allgemeinen where R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 17 , R 18 , R 19 , R 20 , R 22 , R 23 , R 24 , R 25 , R 26 , R 28 , R 29 and R 30 and A 1 to A 9 each have the meaning as defined below, and wherein the arrow for a bond to the respective group CR 6 in the general
Formel (I) steht, Formula (I) stands,
R1 für (Ci-C7)-Alkyl, (C3-C7)-Cycloalkyl, (C4-C7)-Cycloalkenyl, (C2-C7)- Alkenyl, (C2-C7)-Alkinyl, (C2-C7)-Alkenyl-(Ci-C7)-alkyl, (C2-C7)-Alkinyl- (d-C7)-alkyl, (Ci-C7)-Alkoxy-(d-C7)-alkyl, Hydroxy-(d-C7)-alkyl, (C1-C7)- Haloalkyl, (C2-C7)-Haloalkenyl, (C2-C7)-Haloalkinyl, (Ci-C7)-Haloalkoxy- (Ci-C7)-alkyl, (Ci-C7)-Alkoxy-(Ci-C7)-haloalkyl, (Ci-C7)-Haloalkoxy- (CrC7)-haloalkyl, (CrC7)-Alkylthio-(Ci-C7)-alkyl, (Ci-C7)-Haloalkylthio- (Ci-C7)-alkyl steht,
R2, R3 und R4 unabhängig voneinander für Wasserstoff, Halogen, (Ci-C-7)-Alkyl, (C3-C7)-Cycloalkyl, (C4-C7)-Cycloalkenyl, (C2-C7)-Alkenyl, (C2-C7)-Alkinyl, (C2-C7)-Alkenyl-(Ci-C7)-alkyl, (C2-C7)-Alkinyl-(Ci-C7)-alkyl, (C1-C7)- Alkoxy-(Ci-C7)-alkyl, Hydroxy-(Ci-C7)-alkyl, (d-C7)-Haloalkyl, (C2-C7)- Haloalkenyl, (C2-C7)-Haloalkinyl, (Ci-C7)-Haloalkoxy-(Ci-C7)-alkyl, (Ci-C7)-Alkoxy-(Ci-C7)-haloalkyli (Ci-C7)-Haloalkoxy-(Ci-C7)-haloalkyl, (Ci-C7)-Alkylthio-(Ci-C7)-alkyl, (Ci-C7)-Haloalkylthio-(Ci-C7)-alkyl stehen, R 1 is (C 1 -C 7 ) -alkyl, (C 3 -C 7 ) -cycloalkyl, (C 4 -C 7 ) -cycloalkenyl, (C 2 -C 7 ) -alkenyl, (C 2 -C 7 ) -alkynyl, (C 2 -C 7) alkenyl (Ci-C7) alkyl, (C 2 -C 7) alkynyl (dC 7) alkyl, (Ci-C7) alkoxy (dC 7) - alkyl, hydroxy (dC 7) alkyl, (C1-C7) - haloalkyl, (C 2 -C 7) haloalkenyl, (C 2 -C 7) haloalkynyl, (Ci-C7) haloalkoxy (C -C 7) alkyl, (Ci-C7) alkoxy (Ci-C7) haloalkyl, (Ci-C7) haloalkoxy (-C 7) haloalkyl, (CrC 7) alkylthio (C -C 7) alkyl, (Ci-C 7) -Haloalkylthio- (Ci-C7) alkyl, R 2 , R 3 and R 4 independently of one another represent hydrogen, halogen, (C 1 -C 7 ) -alkyl, (C 3 -C 7 ) -cycloalkyl, (C 4 -C 7 ) -cycloalkenyl, (C 2 -C 7) alkenyl, (C 2 -C 7) -alkynyl, (C2-C7) alkenyl (Ci-C7) alkyl, (C 2 -C 7) alkynyl (Ci-C7) - alkyl, (C1-C7) - alkoxy (Ci-C7) alkyl, hydroxy (Ci-C7) alkyl, (dC 7) -haloalkyl, (C2-C7) - haloalkenyl, (C 2 -C 7 ) -haloalkynyl, (C 1 -C 7 ) -haloalkoxy- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -haloalkyl i (C 1 -C 7 ) -haloalkoxy- ( C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -alkylthio (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -haloalkylthio (C 1 -C 7 ) -alkyl,
R5 für Hydroxy, (Ci-C7)-Alkoxy, Aryloxy, (C3-C7)-Cycloalkyloxy, (C2-C7)- Alkenyloxy, (C2-C7)-Alkenyl-(Ci-C7)-alkyloxy, (Ci-C7)-Alkoxy-(Ci-C7)- alkyloxy, (Ci-C7)-Alkylcarbonyloxy, Arylcarbonyloxy, R 5 is hydroxy, (Ci-C7) alkoxy, aryloxy, (C 3 -C 7) cycloalkyloxy, (C2-C7) - alkenyloxy, (C2-C7) alkenyl (Ci-C7) - alkyloxy, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyloxy, (C 1 -C 7 ) -alkylcarbonyloxy, arylcarbonyloxy,
Heteroarylcarbonyloxy, (C3-C7)-Cycloalkylcarbonyloxy, (C1-C7)- Alkoxycarbonyloxy, (C2-C7)-Alkenyloxycarbonyloxy, Aryloxy-(Ci-C7)- alkyloxy, Aryl-(Ci-C7)-alkyloxy, (Ci-C7)-Alkoxy-(Ci-C7)-alkoxy-(Ci-C7)- alkyloxy, (Ci-C7)-Alkylthio-(Ci-C7)-alkyloxy, Tris[(Ci-C7)-alkyl]silyloxy, (Ci-C7)-Alkyl-Bis[(Ci-C7)-alkyl]silyloxy, (Ci-C7)-Alkyl-bis(Aryl)silyloxy, Aryl-bis[(Ci-C7)— alkyljsilyloxy, Cycloalkyl-bis[(Ci-C7)-alkyl]silyloxy, Halo- bis[(Ci-C7)-alkyl]silyloxy, Tris[(Ci-C7)-alkyl]silyl-(Ci-C7)-alkoxy-(Ci-C7)- alkyloxy, steht, Heteroarylcarbonyloxy, (C 3 -C 7) -cycloalkylcarbonyloxy, (C 1 -C 7) -alkoxycarbonyloxy, (C 2 -C 7) -alkenyloxycarbonyloxy, aryloxy- (C 1 -C 7) -alkyloxy, aryl- (C 1 -C 7 ) -alkyloxy, (Ci -C 7) alkoxy (Ci-C7) alkoxy (Ci-C7) - alkyloxy, (Ci-C7) -alkylthio (Ci-C 7) alkyloxy, tris [(Ci-C 7) alkyl] silyloxy, (C 1 -C 7 ) -alkyl bis [(C 1 -C 7 ) -alkyl] silyloxy, (C 1 -C 7 ) -alkyl bis (aryl) silyloxy, aryl bis [(C 1 -C 7 ) Alkyljsilyloxy, cycloalkylbis [(Ci-C 7 ) -alkyl] silyloxy, halo bis [(Ci-C 7 ) alkyl] silyloxy, tris [(Ci-C7) alkyl] silyl (Ci-C 7 ) -alkoxy- (C 1 -C 7 ) -alkyloxy,
R6 für (C1-C7)- Alkylsulfonylaminocarbonyl, (C3-C7)-R 6 is (C 1 -C 7 ) -alkylsulfonylaminocarbonyl, (C 3 -C 7) -
Cycloalkylsulfonylaminocarbonyl, Hydroxycarbonyl, (C1-C7)- Alkoxycarbonyl, (C3-C-7)-Cycloalkoxycarbonyl, (C3-C7)-Cycloalkyl-(d-C7)- alkoxycarbonyl, Aryloxycarbonyl, Aryl-(d-C7)-alkoxycarbonyl, (C2-C7)- Alkenyloxycarbonyl, (C2-C7)-Alkinyloxycarbonyl, (C1-C7)- Haloalkyloxycarbonyl, (Ci-C7)-Alkoxy-(d-C7)-alkoxycarbonyl, (C2-C7)- Alkenyloxy-(Ci-C7)-alkoxycarbonyl, (Ci-C7)-Alkylamino-(Ci-C7)- alkoxycarbonyl, Tris[(Ci-C7)-alkyl]silyloxy-(Ci-C7)-alkoxycarbonyl, Bis[(Ci-C7)-Alkyl]amino-(Ci-C7)-alkoxycarbonyl, (Ci-C7)-Alkyl[(Ci-C7)- alkyl]amino-(Ci-C7)-alkoxycarbonyl, Cyano-(Ci-C7)-alkoxycarbonyl, Heterocyclyl-N-(Ci-C7)-alkoxycarbonyl, Heteroaryloxycarbonyl, Cycloalkylsulfonylaminocarbonyl, hydroxycarbonyl, (C 1 -C 7) -alkoxycarbonyl, (C 3 -C-7) -cycloalkoxycarbonyl, (C 3 -C 7) -cycloalkyl- (C 1 -C 7) -alkoxycarbonyl, aryloxycarbonyl, aryl- (C 1 -C 7) -alkoxycarbonyl, (C 2 -C 7) -alkenyloxycarbonyl, (C 2 -C 7) -alkynyloxycarbonyl, (C 1 -C 7) -haloalkyloxycarbonyl, (C 1 -C 7) -alkoxy- (C 1 -C 7) -alkoxycarbonyl, (C 2 -C 7) -alkenyloxy- (C 1 -C 7) -alkoxycarbonyl, (C 1 -C 7) -alkylamino- (C 1 -C 7) -alkoxycarbonyl, tris [(C 1 -C 7) -alkyl] silyloxy- (C 1 -C 7) -alkoxycarbonyl, bis [(C 1 -C 4 -alkyl) 7 ) -alkyl] amino- (C 1 -C 7 ) -alkoxycarbonyl, (C 1 -C 7 ) -alkyl [(C 1 -C 7 ) -alkyl] amino- (C 1 -C 7 ) -alkoxycarbonyl, cyano- (C 1 -C 7 ) - alkoxycarbonyl, heterocyclyl-N- (C 1 -C 7) -alkoxycarbonyl, heteroaryloxycarbonyl,
Heteroaryl-(d-C7)-alkoxycarbonyl, Heterocyclyl-(CrC7)-alkoxycarbonyl, Heterocyclyloxycarbonyl, (C2-C7)-Alkenyl-(Ci-C7)-alkoxycarbonyl, Heteroaryl- (C 1 -C 7) -alkoxycarbonyl, heterocyclyl- (C 1 -C 7) -alkoxycarbonyl, heterocyclyloxycarbonyl, (C 2 -C 7) -alkenyl- (C 1 -C 7) -alkoxycarbonyl,
(C2-C7)-Alkinyl-(Ci-C7)-alkoxycarbonyl, Aryl-(C2-C7)-alkinyloxycarbonyl,
Aryl-(C2-C7)-alkenyloxycarbonyl, Aminocarbonyl, (C1-C7)- Alkylaminocarbonyl, Bis[(CrC7)-alkyl]aminocarbonyl, (C1-C7)- Alkyl[(Ci-C7)-Alkyl]aminocarbonyl, (Ci-C7)-Alkyl[(Ci-C7)- Alkoxy]aminocarbonyl, (C2-C7)-Alkenylaminocarbonyl, (C3-C7)- Cycloalkylaminocarbonyl, Arylaminocarbonyl, Aryl-(d-C7)- alkylaminocarbonyl, Heteroaryl-(Ci-C7)-alkylaminocarbonyi, Cyano- (Ci-C7)-alkylaminocarbonyi, (Ci-C7)-Haioalkylaminocarbonyl, (C2-C7)- Alkinyl-(Ci-C7)-alkylaminocarbonyl, (C1-C7)- Alkoxycarbonylaminocarbonyl, Ary!-(Ci-C7)- alkoxycarbonylaminocarbonyl, Hydroxycarbonyl-(Ci-C7)-alkyl, (C1-C7)- Alkoxycarbonyl-(Ci-C7)-alkyl, (C3-C7)-Cycloalkoxycarbonyl-(CrC7)-alkyl, (C3-C7)-Cycloalkyl-(Ci-C7)-alkoxycarbonyl-(Ci-C7)-alkyl, (C2-C7)- Alkenyloxycarbonyl-(Ci-C7)-alkyl, Aryl-(Ci-C7)-alkoxycarbonyl-(Ci-C7)- alkyl, (Ci-C7)-Alkylaminocarbonyl-(CrC7)-alkyl, Aminocarbonyl-(Ci-C7)- alkyl, Bis[(Ci-C7)-alkyl]aminocarbonyl-(Ci-C7)-alkyl, (C3-C7)- Cycloalkylaminocarbonyl-(CrC7)-alkyl, Aryl-(CrC7)-alkylaminocarbonyl- (d-C7)-alkyl, Heteroaryl-(CrC7)-alkylaminocarbonyl-(Ci-C7)-alkyl, Cyano-(Ci-C7)-alkylaminocarbonyl-(Ci-C7)-alkyl, (C1-C7)- Haloalkylaminocarbonyl-(Ci-C7)-alkyl, (C2-C7)-Alkinyl-(Ci-C7)- alkylaminocarbonyl-(Ci-C7)-alkyl, (C3-C7)-Cycloalkyl-(Ci-C7)- alkylaminocarbonyl-(CrC7)-alkyl, (Ci-C7)-Alkoxycarbonylaminocarbonyl- (Ci-C7)-alkyl, Aryl-(Ci-C7)-alkoxycarbonylaminocarbonyl-(Ci-C7)-alkyl, (Ci-C7)-Alkoxycarbonyl-(CrC7)-alkylaminocarbonyl, Hydroxycarbonyl- (Ci-C7)-alkylaminocarbonyl, Aryl-(d-C7)-alkoxycarbonyl-(Ci-C7)- alkylaminocarbonyl, Aminocarbonyl-(Ci-C7)-alkylaminocarbonyl, (C1-C7)- Alkylaminocarbonyl-(Ci-C7)-alkylaminocarbonyl. (C 2 -C 7) -alkynyl- (C 1 -C 7) -alkoxycarbonyl, aryl- (C 2 -C 7) -alkynyloxycarbonyl, Aryl- (C 2 -C 7 ) -alkenyloxycarbonyl, aminocarbonyl, (C 1 -C 7 ) -alkylaminocarbonyl, bis [(C 1 -C 7 ) -alkyl] -aminocarbonyl, (C 1 -C 7 ) -alkyl [(C 1 -C 7 ) -alkyl] -aminocarbonyl, ( C 1 -C 7 ) -alkyl [(C 1 -C 7 ) -alkoxy] -aminocarbonyl, (C 2 -C 7 ) -alkenylaminocarbonyl, (C 3 -C 7 ) -cycloalkylaminocarbonyl, arylaminocarbonyl, aryl- (C 1 -C 7 ) -alkylaminocarbonyl, heteroaryl- C 1 -C 7) -alkylaminocarbonyi, cyano- (C 1 -C 7) -alkylaminocarbonyi, (C 1 -C 7) -hioalkylaminocarbonyl, (C 2 -C 7) -alkynyl- (C 1 -C 7) -alkylaminocarbonyl, (C 1 -C 7) -alkoxycarbonylaminocarbonyl, Ary ! - (C 1 -C 7) -alkoxycarbonylaminocarbonyl, hydroxycarbonyl- (C 1 -C 7) -alkyl, (C 1 -C 7) -alkoxycarbonyl- (C 1 -C 7) -alkyl, (C 3 -C 7) -cycloalkoxycarbonyl- (C 1 -C 7) -alkyl, (C 3 -C 7 ) -cycloalkyl- (C 1 -C 7 ) -alkoxycarbonyl- (C 1 -C 7 ) -alkyl, (C 2 -C 7 ) -alkenyloxycarbonyl- (C 1 -C 7 ) -alkyl, aryl- (C 1 -C 7 ) - alkoxycarbonyl- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkylaminocarbonyl- (C 1 -C 7 ) -alkyl, aminocarbonyl- (C 1 -C 7 ) -alkyl, bis [(C 1 -C 7 ) -alkyl] aminocarbonyl- (C 1 -C 4 ) -alkyl C7) -alkyl, (C3-C7) -cycloalkylaminocarbonyl- (CrC7) -alkyl, aryl- (CrC7) -alkylamine ocarbonyl- (C 1 -C 7) -alkyl, heteroaryl- (C 1 -C 7) -alkylaminocarbonyl- (C 1 -C 7) -alkyl, cyano- (C 1 -C 7) -alkylaminocarbonyl- (C 1 -C 7) -alkyl, (C 1 -C 7) - Haloalkylaminocarbonyl- (Ci-C7) alkyl, (C2-C7) alkynyl (Ci-C7) - alkylaminocarbonyl (Ci-C7) alkyl, (C3-C7) -cycloalkyl- (Ci-C 7 ) - alkylaminocarbonyl- (C 1 -C 7) -alkyl, (C 1 -C 7) -alkoxycarbonylaminocarbonyl- (C 1 -C 7) -alkyl, aryl- (C 1 -C 7) -alkoxycarbonylaminocarbonyl- (C 1 -C 7) -alkyl, (C 1 -C 7) - Alkoxycarbonyl- (C 1 -C 7) -alkylaminocarbonyl, hydroxycarbonyl- (C 1 -C 7) -alkylaminocarbonyl, aryl- (C 1 -C 7) -alkoxycarbonyl- (C 1 -C 7) -alkylaminocarbonyl, aminocarbonyl- (C 1 -C 7) -alkylaminocarbonyl, (C 1 -C 7 ) - Alkylaminocarbonyl- (Ci-C7) -alkylaminocarbonyl.
(C3-C7)-Cycloalkylaminocarbony!-(Ci-C7)-alkylaminocarbonyl, (C3-C7)- Cycloalkyl-(Ci-C7)-alkylaminocarbonyl, Aminosulfonyl, (Ci-Cs)- Alkoxycarbonyl-heterocyclyl-N-carbonyl, (Ci-C8)-Alkoxycarbonyl-(Ci-C8)- alkyl-heterocyclylidenaminocarbonyl, (d-Cs)- Alkoxycarbonylheterocyclyliden-(Ci-C8)-alkylaminocarbonyl (d-Ce)- Alkoxycarbonyl-(CrC8)-Alkyl((Ci-C8)-alkyl)aminocarbonyl, (d-Cs)- Alkoxycarbonyl-(C3-C8)-cycloalkylidenaminocarbonyl, Heterocyclyl-N- carbonyl, (Ci-C7)-Alkoxy-(Ci-C7)-alkylaminocarbonyl, (C3-C7)-Cycloaikyl-
(Ci-C7)-alkylaminocarbonyl-(Ci-C7)-alkyl, (C3-C7)-Cycloalkyl-(Ci-C7)- alkylaminocarbonyl-(Ci-C7)-alkylaminocarbonyl, (C2-C7)-Alkenyl-(Ci-C7)- alkylaminocarbonyl, (C2-C7)-Alkenylaminocarbonyl-(Ci-C7)-alkyl, (C2-C7)- Alkenyl-(Ci-C7)-alkylaminocarbonyl-(Ci-C7)-alkyl, (d-C7)-Alkylcarbonyl, (C3-C7)-Cycloalkylcarbonyl, Arylcarbonyl, Formyl, Hydroxyiminomethyl, Aminoiminomethyl, (Ci-C7)-Alkoxyiminomethyl, (C1-C7)- Alkylaminoiminomethyl, Bis[(Ci-C7)-alkyl]aminoiminomethyl, (C3-C7)- Cycloalkoxyiminomethyl, (C:rC7)-Cycloalkyl-(Ci-C7)-alkoximinomethyl, Aryloximinomethyl, Aryl-(Ci-C7)-alkoxyiminomethyl, Aryl-(Ci-C7)- alkylaminoiminomethyl, (C2-C7)-Alkenyloxyiminomethyl, (C 3 -C 7) -cycloalkylaminocarbonyl- (C 1 -C 7) -alkylaminocarbonyl, (C 3 -C 7) -cycloalkyl- (C 1 -C 7) -alkylaminocarbonyl, aminosulfonyl, (C 1 -C 8) -alkoxycarbonyl-heterocyclyl-N-carbonyl, ( C 1 -C 8) -alkoxycarbonyl- (C 1 -C 8) -alkyl-heterocyclylideneaminocarbonyl, (C 1 -C 5) -alkoxycarbonylheterocyclylidene- (C 1 -C 8) -alkylaminocarbonyl (C 1 -C 6) -alkoxycarbonyl- (C 1 -C 8) -alkyl ((C 1 -C 8) -cyclo-C 1 -C 4 -alkyl) ) -alkyl) aminocarbonyl, (d-Cs) - alkoxycarbonyl- (C3-C8) -cycloalkylidene-aminocarbonyl, heterocyclyl-N-carbonyl, (Ci-C7) -alkoxy- (Ci-C7) -alkylaminocarbonyl, (C3-C7) - Cycloaikyl- (Ci-C7) alkylaminocarbonyl (Ci-C7) alkyl, (C 3 -C 7) cycloalkyl (Ci-C7) - alkylaminocarbonyl (Ci-C 7) alkylaminocarbonyl, (C2-C7 ) -Alkenyl- (C 1 -C 7 ) -alkylaminocarbonyl, (C 2 -C 7 ) -alkenylaminocarbonyl (C 1 -C 7 ) -alkyl, (C 2 -C 7 ) -alkenyl- (C 1 -C 7 ) -alkylaminocarbonyl- (Ci -C 7) alkyl, (dC 7) alkylcarbonyl, (C3-C7) cycloalkylcarbonyl, arylcarbonyl, formyl, hydroxyiminomethyl, aminoiminomethyl, (Ci-C 7) alkoxyiminomethyl, (C1-C7) - Alkylaminoiminomethyl, bis [ (C 1 -C 7 ) -alkyl] aminoiminomethyl, (C 3 -C 7 ) -cycloalkoxyiminomethyl, (C: rC 7 ) -cycloalkyl- (C 1 -C 7 ) -alkoximinomethyl, aryloximinomethyl, aryl- (C 1 -C 7 ) -alkoxyiminomethyl, aryl- (C 1 -C 7) -alkylaminoiminomethyl, (C 2 -C 7) -alkenyloxyiminomethyl,
Arylaminoiminomethyl, Arylsulfonylaminoiminomethyl, Arylaminoiminomethyl, arylsulfonylaminoiminomethyl,
Hydroxycarbonylheterocyclyl-(Ci-C7)-alkyl, (C1-C7)- Alkoxycarbonylheterocyclyl-(CrC7)-alkyl, Hydroxycarbonyl-(C3-C7)- cycloalkyl-(Ci-C7)-alkyl, (Ci-C7)-Alkoxycarbonyl-(C3-C7)-cycloalkyl- (Ci-C7)-alkyl, Hydroxyaminocarbonyl, (Ci-C7)-Alkoxyaminocarbonyl, Aryl- (CrC7)-alkoxyaminocarbonyl steht, Hydroxycarbonylheterocyclyl- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkoxycarbonyl-heterocyclyl- (C 1 -C 7 ) -alkyl, hydroxycarbonyl- (C 3 -C 7 ) -cycloalkyl- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) - Alkoxycarbonyl- (C 3 -C 7 ) -cycloalkyl- (C 1 -C 7 ) -alkyl, hydroxyaminocarbonyl, (C 1 -C 7 ) -alkoxyaminocarbonyl, aryl- (C 1 -C 7 ) -alkoxyaminocarbonyl,
R7, R8 , R9 und R10 unabhängig voneinander für Wasserstoff, Halogen, Nitro,R 7 , R 8 , R 9 and R 10 independently of one another represent hydrogen, halogen, nitro,
Amino, Cyano, (Ci-C7)-Alkyl, Aryl, Heteroaryl, (C3-C7)-Cycloalkyl, (C4-C7)- Cycloalkenyl, (C2-C7)-Alkenyl, (C2-C7)-Alkinyl, (C2-C7)-Alkenyl-(Ci-C7)- alkyl, (C2-C7)-Alkinyl-(Ci-C7)-alkyl, Hydroxy, (Ci-C7)-Alkoxy, (C1-C7)- Alkoxy-(CrC7)-alkoxy, (Ci-C7)-Alkoxy-(Ci-C7)-alkyl, Hydroxy-(Ci-C7)- alkyl, (CrC7)-Haloalkoxy, (Ci-C7)-Haloalkyl, (C2-C7)-Haloalkenyl, (C2-C7)- Haloalkinyl, (Ci-C7)-Haloalkoxy-(Ci-C7)-alkyl, (Ci-C7)-Alkoxy-(Ci-C7)- haloalkyl, (Ci-C7)-Haloalkoxy-(Ci-C7)-haloalkyl, Hydrothio, (C1-C7)- Alkylthio, (Ci-C7)-Haloalkylthio, (Ci-C7)-Alkylthio-(Ci-C7)-aikyl, (C1-C7)- Haloalkylthio-(Ci-C7)-aikyl, (Ci-C7)-Alkylamino, Bis[(Ci-C7)-alkyl]amino, (C2-C7)-Alkenylamino, (C3-C7)-Cycloalkylamino, (C1-C7)- Alkylcarbonylamino, (C3-C7)-Cycloalkylcarbonylamino, Amino, cyano, (C 1 -C 7 ) -alkyl, aryl, heteroaryl, (C 3 -C 7 ) -cycloalkyl, (C 4 -C 7 ) -cycloalkenyl, (C 2 -C 7 ) -alkenyl, (C 2 -C 7 ) - alkynyl, (C 2 -C 7) alkenyl (Ci-C7) - alkyl, (C2-C7) alkynyl (Ci-C7) alkyl, hydroxy, (Ci-C7) alkoxy, ( C1-C7) - alkoxy (-C 7) alkoxy, (Ci-C7) alkoxy (Ci-C7) alkyl, hydroxy (Ci-C7) - alkyl, (CrC 7) haloalkoxy, (Ci-C7) haloalkyl, (C 2 -C 7) haloalkenyl, (C2-C7) - haloalkynyl, (Ci-C7) haloalkoxy (Ci-C7) alkyl, (Ci-C 7 ) -Alkoxy- (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -haloalkoxy- (C 1 -C 7 ) -haloalkyl, hydrothio, (C 1 -C 7 ) -alkylthio, (C 1 -C 7 ) -haloalkylthio, (C 1 -C 7 ) -alkylthio (C 1 -C 7 ) -acyl, (C 1 -C 7 ) -haloalkylthio (C 1 -C 7 ) -acyl, (C 1 -C 7 ) -alkylamino, bis [(C 1 -C 4 -alkyl) 7 ) -alkyl] amino, (C 2 -C 7 ) -alkenylamino, (C 3 -C 7 ) -cycloalkylamino, (C 1 -C 7 ) -alkylcarbonylamino, (C 3 -C 7 ) -cycloalkylcarbonylamino,
Arylcarbonylamino, Heteroarylcarbonylamino, Formylamino, (C1-C7)- Haloalkylcarbonylamino, (Ci-C7)-Alkoxycarbonylamino, (C1-C7)- Alkylaminocarbonylamino, (Ci-C7)-Alkyl[(d-C7)- Alkyljaminocarbonylamino, (Ci-C7)-Alkylsulfonylamino, (C3-C7)- Cycloalkylsulfonylamino, Arylsulfonylamino, Hetarylsulfonylamino,
Sulfonyl-(Ci-C7)-haloalkylamino, Amino-(Ci-C7)-alkylsulfonyl, Amino- (Ci-C7)-haloalkylsulfonyl, (Ci-C7)-Alkylaminosulfonyl, Bis[(CrC7)- alkyljaminosulfonyl, (C3-C7)-Cycloalkylaminosulfonyl, (C1-C7)- Haloalkylaminosulfonyl, Heteroarylaminosulfonyl, Arylaminosulfonyl, Aryl- (Ci-C7)-alkylaminosulfonyl, (Ci-C7)-Alkylsulfonyl, (C3-C7)- Cycloalkylsulfonyl, Arylsulfonyl, Hydroxycarbonyl, (C1-C7)- Alkoxycarbonyl, (C3-C-7)-Cycloalkoxycarbonyl, (C3-C7)-Cycloalkyl-(CrC7)- alkoxycarbonyl, Aryloxycarbonyl, Aryl-(Ci-C7)-alkoxycarbonyl, (C2-C7)- Alkenyloxycarbonyl, (C2-C7)-Alkinyloxycarbonyl, Aminocarbonyl, (C1-C7)- Alkylaminocarbonyl, Bis[(Ci-C7)-alkyl]aminocarbonyl, (C1-C7)- Alkyl[(Ci-C7)-Alkyl]aminocarbonyl, (Ci-C7)-Alkyl[(Ci-C7)- Alkoxyjaminocarbonyl, (C2-C7)-Alkenylaminocarbonyl, (C3-C7)- Cycloalkylaminocarbonyl, Arylaminocarbonyl, Aryl-(d-C7)- alkylaminocarbonyl stehen, Arylcarbonylamino, heteroarylcarbonylamino, formylamino, (C 1 -C 7) -haloalkylcarbonylamino, (C 1 -C 7) -alkoxycarbonylamino, (C 1 -C 7) -alkylaminocarbonylamino, (C 1 -C 7) -alkyl [(C 1 -C 7) -alkylaminocarbonylamino, (C 1 -C 7) ) -Alkylsulfonylamino, (C3-C7) -cycloalkylsulfonylamino, arylsulfonylamino, hetarylsulfonylamino, Sulfonyl- (C 1 -C 7 ) -haloalkylamino, amino- (C 1 -C 7 ) -alkylsulfonyl, amino- (C 1 -C 7 ) -haloalkylsulfonyl, (C 1 -C 7 ) -alkylaminosulfonyl, bis [(C 1 -C 7 ) -alkylaminosulfonyl, ( C 3 -C 7 -cycloalkylaminosulfonyl, (C 1 -C 7 ) -haloalkylaminosulfonyl, heteroarylaminosulfonyl, arylaminosulfonyl, aryl- (C 1 -C 7 ) -alkylaminosulfonyl, (C 1 -C 7 ) -alkylsulfonyl, (C 3 -C 7 ) -cycloalkylsulfonyl, arylsulfonyl, Hydroxycarbonyl, (C 1 -C 7) alkoxycarbonyl, (C 3 -C 7) cycloalkoxycarbonyl, (C 3 -C 7) cycloalkyl- (C 1 -C 7) alkoxycarbonyl, aryloxycarbonyl, aryl- (C 1 -C 7) alkoxycarbonyl, (C 2 -C 7 ) - alkenyloxycarbonyl, (C 2 -C 7) -alkynyloxycarbonyl, aminocarbonyl, (C 1 -C 7 ) -alkylaminocarbonyl, bis [(C 1 -C 7 ) -alkyl] aminocarbonyl, (C 1 -C 7 ) -alkyl [(C 1 -C 7 ) -alkyl ] aminocarbonyl, (Ci-C 7) alkyl [(Ci-C 7) - (d-C7) cycloalkylaminocarbonyl, arylaminocarbonyl, aryl - - are alkylaminocarbonyl, Alkoxyjaminocarbonyl, (C2-C7) -Alkenylaminocarbonyl, (C3-C7)
A1 , A2, A3 und A4 gleich oder verschieden sind und unabhängig voneinander für N (Stickstoff) oder die Gruppierungen C-H, C-CH3, C-F, C-Cl, C-Br, C-l, C-OCF3, C-OCH3, C-CF3, C-CO2H, C-CO2CH3 stehen, wobei jedoch in keinem Fall mehr als zwei N-Atome benachbart sind, A 1 , A 2 , A 3 and A 4 are the same or different and are each independently N (nitrogen) or the groupings CH, C-CH 3 , CF, C-Cl, C-Br, Cl, C-OCF 3, C -OCH 3, C-CF 3, C-CO2H, C-CO2CH3 are, but in no case more than two N atoms are adjacent,
R11 und R12 unabhängig voneinander für Wasserstoff, Halogen, (CrC-7)-Alkyl, Aryl, Heteroaryl, Heterocyclyl, (C3-C-7)-Cycloalkyl, (C2-C7)-Alkenyl, (C2-C7)-Alkinyl, (Ci-C7)-Alkoxy, (Ci-C7)-Alkoxy-(Ci-C7)-alkyl, Aryloxy- (CrC7)-alkyl, (Ci-C7)-Haloalkoxy, (Ci-C7)-Haloalkyl, (Ci-C7)-Haloalkoxy- (Ci-C7)-alkyl, (Ci-C7)-Alkoxy-(Ci-C7)-haloalkyl, (Ci-C7)-Haloalkoxy- (CrC7)-haloalkyl, (CrC7)-Alkylthio, (Ci-C7)-Haloalkylthio, (C1-C7)- Alkylthio-(Ci-C7)-alkyl, Hydroxycarbonyl, (Ci-C7)-Alkoxycarbonyl, (C3-C7)- Cycloalkoxycarbonyl, (C3-C7)-Cycloalkyl-(Ci-C7)-alkoxycarbonyl, R 11 and R 12 independently of one another represent hydrogen, halogen, (C 1 -C 7 ) -alkyl, aryl, heteroaryl, heterocyclyl, (C 3 -C 7 ) -cycloalkyl, (C 2 -C 7 ) -alkenyl, (C 2 -C 7) ) -Alkynyl, (C 1 -C 7 ) -alkoxy, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, aryloxy- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -haloalkoxy, ( C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -haloalkoxy- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) haloalkoxy (-C 7) haloalkyl, (CrC 7) alkylthio, (Ci-C 7) haloalkylthio, (C1-C7) - alkylthio (Ci-C7) alkyl, hydroxycarbonyl, (Ci-C7) - Alkoxycarbonyl, (C 3 -C 7) -cycloalkoxycarbonyl, (C 3 -C 7) -cycloalkyl- (C 1 -C 7) -alkoxycarbonyl,
Aryloxycarbonyl, Aryl-(Ci-C7)-alkoxycarbonyl, (C2-C7)- Alkenyloxycarbonyl, (C2-C7)-Alkinyloxycarbonyl, Aminocarbonyl, (C1-C7)- Alkylaminocarbonyl, Bis[(Ci-C7)-alkyl]aminocarbonyl, (C1-C7)- Alkyl[(Ci-C7)-Alkyl]aminocarbonyl, (Ci-C7)-Alkyl[(Ci-C7)- Alkoxyjaminocarbonyl, (C2-C7)-Alkenylaminocarbonyl, (C3-C7)-
Cycloalkylaminocarbonyl, Arylaminocarbonyl, Aryl-(Ci-C-7)- alkylaminocarbonyl stehen, Aryloxycarbonyl, aryl- (C 1 -C 7) -alkoxycarbonyl, (C 2 -C 7) -alkenyloxycarbonyl, (C 2 -C 7) -alkynyloxycarbonyl, aminocarbonyl, (C 1 -C 7) -alkylaminocarbonyl, bis [(C 1 -C 7) -alkyl] aminocarbonyl, (C 1 -C 7 ) -alkyl [(C 1 -C 7 ) -alkyl] aminocarbonyl, (C 1 -C 7 ) -alkyl [(C 1 -C 7 ) -alkoxy] -aminocarbonyl, (C 2 -C 7 ) -alkenylaminocarbonyl, (C 3 -C 7 ) - Cycloalkylaminocarbonyl, arylaminocarbonyl, aryl- (Ci-C-7) -alkylaminocarbonyl,
A5 für S (Schwefel), O (Sauerstoff) oder die Gruppierungen N-H, N-Ch , N- CH2CH3, N-CH(CH3)2, N-C02t-Bu, N-Aryl, N-Heteroaryl, N-Heterocyclyl steht, A 5 represents S (sulfur), O (oxygen) or the groupings NH, N-CH, N-CH 2 CH 3 , N-CH (CH 3 ) 2 , N-CO 2 t-Bu, N-aryl, N-heteroaryl, N-heterocyclyl is
R13, R14, R17 und R18 unabhängig voneinander für Wasserstoff, (Ci-C7)-Alkyl, Halogen, (C3-C7)-Cycloalkyl, Aryl, Heteroaryl, Heterocyclyl, (C2-C7)- Alkenyl, (C2-C7)-Alkenyl-(Ci-C7)-alkyl, Aryl-(Ci-C7)-alkyl, (Ci-C7)-Alkoxy,R 13 , R 14 , R 17 and R 18 independently of one another represent hydrogen, (C 1 -C 7) -alkyl, halogen, (C 3 -C 7) -cycloalkyl, aryl, heteroaryl, heterocyclyl, (C 2 -C 7) -alkenyl, (C 2 -C 4) -alkyl -C 7) -alkenyl- (C 1 -C 7 ) -alkyl, aryl- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkoxy,
(Ci-C7)-Alkoxy-(Ci-C7)-alkoxy, (Ci-C7)-Alkoxy-(Ci-C7)-alkyl, Hydroxy, (Ci-C7)-Haloalkyl, (Ci-C7)-Haloalkylthio stehen oder (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkoxy, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, hydroxy, (C 1 -C 7 ) -haloalkyl, C 7 ) haloalkylthio or
R13 und R17 mit den Atomen, an die sie gebunden sind, einen vollständig R 13 and R 17 complete with the atoms to which they are attached
gesättigten oder teilgesättigten, gegebenenfalls weiter substituierten 5 bis 7-gliedrigen Ring bilden, form a saturated or partially saturated, optionally further substituted 5 to 7-membered ring,
A6, A7 gleich oder verschieden sind und unabhängig voneinander für O A 6 , A 7 are the same or different and are each independently O.
(Sauerstoff), S (Schwefel), N-H, N-OCH3, N-CH3 oder die Gruppierung CR15R16 stehen, wobei jedoch in keinem Fall zwei N-, O- oder S-Atome benachbart sind, und wobei R15 und R16 in der Gruppierung CR15R16 jeweils gleiche oder verschiedene Bedeutungen gemäß der (Oxygen), S (sulfur), NH, N-OCH 3, N-CH3 or the group CR 15 R 16, but in no case two N, O or S atoms are adjacent, and wherein R 15 and R 16 in the group CR 15 R 16 each have the same or different meanings according to the
nachstehenden Definition haben und have the following definition and
R15 und R16 unabhängig voneinander für Wasserstoff, Halogen, (C1-C7)- Alkyl, Aryl, Heteroaryl, Heterocyclyl, (C3-C7)-Cycloalkyl, (C2-C7)-Alkenyl, R 15 and R 16 independently of one another represent hydrogen, halogen, (C 1 -C 7) -alkyl, aryl, heteroaryl, heterocyclyl, (C 3 -C 7) -cycloalkyl, (C 2 -C 7) -alkenyl,
(Ci-C7)-Alkoxy, (Ci-C7)-Alkoxy-(Ci-C7)-alkyl, Aryloxy-(Ci-C7)-alkyl, (Ci-C7)-Haloalkoxy, (Ci-C7)-Haloalkyl, (Ci-C7)-Haloalkoxy(Ci-C7)-alkyl, (Ci-C7)-Alkoxy-(Ci-C7)-haloalkyl, (Ci-C7)-Haloalkoxy-(Ci-C7)-haloalkyl, (CrC7)-Alkylthio, (CrC7)-Haloalkylthio, (Ci-C7)-Alkylthio-(Ci-C7)-aikyl, Hydroxycarbonyl, (d-C7)-Alkoxycarbonyl, (C3-C7)-Cycloalkoxycarbonyl, (C3-C7)-Cycloalkyl-(Ci-C7)-alkoxycarbonyl, Aryloxycarbonyl, Aryl-(d-C7)- alkoxycarbonyl , (C2-C7)-Alkenyloxycarbonyl , (C2-C7)-Al ki nyloxycarbonyl , Aminocarbonyl, (Ci-C7)-Alkylaminocarbonyl, Bis[(d-C7)-
alkyljaminocarbonyl, (Ci-C7)-Alkyl[(Ci-C7)-Alkyl]aminocarbonyl, (C1-C7)- Alkyl[(Ci-C7)-Alkoxy]aminocarbonyl, (C2-C7)-Alkenylaminocarbonyl, (C 1 -C 7 ) -alkoxy, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, aryloxy- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -haloalkoxy, (C 1 -C-C) 7 ) -haloalkyl, (C 1 -C 7 ) -haloalkoxy (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -haloalkoxy- (ci) C7) haloalkyl, (CrC 7) alkylthio, (CrC 7) haloalkylthio, (Ci-C7) -alkylthio (Ci-C 7) -alkyl, hydroxycarbonyl, (d-C7) alkoxycarbonyl, (C3- C7) -cycloalkoxycarbonyl, (C3-C7) -cycloalkyl- (Ci-C7) -alkoxycarbonyl, aryloxycarbonyl, aryl- (d-C7) -alkoxycarbonyl, (C2-C7) -alkenyloxycarbonyl, (C2-C7) -alkyloxycarbonyl , Aminocarbonyl, (Ci-C7) -alkylaminocarbonyl, bis [(d-C7) - alkyl-aminocarbonyl, (C 1 -C 7) -alkyl [(C 1 -C 7) -alkyl] aminocarbonyl, (C 1 -C 7) -alkyl [(C 1 -C 7) -alkoxy] -aminocarbonyl, (C 2 -C 7) -alkenylaminocarbonyl,
(C3-C7)-Cycloalkylaminocarbonyl, Arylaminocarbonyl, Aryl-(d-C7)- alkylaminocarbonyl, Amino, (Ci-C7)-Alkylamino,
(C 3 -C 7) -cycloalkylaminocarbonyl, arylaminocarbonyl, aryl- (C 1 -C 7) -alkylaminocarbonyl, amino, (C 1 -C 7) -alkylamino,
Bis-[(Ci-C7)-Alkyl]amino stehen, Bis - [(Ci-C7) -alkyl] amino,
R19, R20, R22 und R23 unabhängig voneinander für Wasserstoff, (d-C7)-Alkyl, Halogen, (C3-C7)-Cycloalkyl, Aryl, Heteroaryl, Heterocyclyi, (C2-C7)- Alkenyl, Aryl-(Ci-C7)-alkyl, (Ci-C7)-Alkoxy, (Ci-C7)-Alkoxy-(Ci-C7)-alkoxy,R 19 , R 20 , R 22 and R 23 independently of one another represent hydrogen, (C 1 -C 7) -alkyl, halogen, (C 3 -C 7) -cycloalkyl, aryl, heteroaryl, heterocyclic, (C 2 -C 7) -alkenyl, aryl- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkoxy, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkoxy,
(Ci-C7)-Alkoxy-(Ci-C7)-alkyl, (Ci-C7)-Haloalkyl stehen, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -haloalkyl,
A8 für O (Sauerstoff), S (Schwefel), N-H, N-CH3, N-OCH3 oder die Gruppierung CHR21 steht und wobei R21 in der Gruppierung CHR21 die Bedeutung gemäß der nachstehenden Definition hat, A 8 is O (oxygen), S (sulfur), NH, N-CH 3 , N-OCH 3 or the moiety CHR 21 , and wherein R 21 in the moiety CHR 21 has the meaning as defined below,
R2i für Wasserstoff, Halogen, (Ci-C7)-Alkyl, Aryl, Heteroaryl, Heterocyclyi, R 2i is hydrogen, halogen, (C 1 -C 7) -alkyl, aryl, heteroaryl, heterocyclic,
(C3-C7)-Cycloalkyl, (C2-C7)-Alkenyl, (Ci-C7)-Alkoxy, (Ci-C7)-Alkoxy- (Ci-C7)-alkyl, Aryloxy-(Ci-C7)-alkyl, (Ci-C7)-Haloalkoxy, (Ci-C7)-Haloalkyl, (Ci-C7)-Alkoxy-(Ci-C7)-haloalkyl, (Ci-C7)-Haloalkoxy-(Ci-C7)-haloalkyl, (Ci-C7)-Alkylthio, (Ci-C7)-Haloalkylthio, (Ci-C7)-Alkylthio-(Ci-C7)-alkyl, Hydroxycarbonyl, (Ci-C7)-Alkoxycarbonyl, (C-3-C7)-Cycloalkoxycarbonyl, Aryl-(d-C7)-alkoxycarbonyl, (C2-C7)-Alkenyloxycarbonyl, (C2-C7)- Alkinyioxycarbonyl, Aminocarbonyl, (Ci-C7)-Alkylaminocarbonyl, (C 3 -C 7) cycloalkyl, (C 2 -C 7) alkenyl, (Ci-C7) alkoxy, (Ci-C7) alkoxy (Ci-C7) alkyl, aryloxy ( C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -haloalkoxy, (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -haloalkoxy - (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -alkylthio, (C 1 -C 7 ) -haloalkylthio, (C 1 -C 7 ) -alkylthio (C 1 -C 7 ) -alkyl, hydroxycarbonyl, (Ci -C7) -alkoxycarbonyl, (C-3-C7) -cycloalkoxycarbonyl, aryl- (d-C7) -alkoxycarbonyl, (C 2 -C 7) -alkenyloxycarbonyl, (C 2 -C 7) -alkynyloxycarbonyl, aminocarbonyl, (C 1 -C 7) - alkylaminocarbonyl,
Bis[(Ci-C7)-alkyl]aminocarbonyl, (Ci-C7)-Alkyl[(Ci-C7)- Alkyl]aminocarbonyl, (Ci-C7)-Alkyl[(CrC7)-Alkoxy]aminocarbonyl, (C2-C7)-Alkenylaminocarbonyl, (C3-C7)-Cycloalkylaminocarbonyl, Bis [(Ci-C 7) alkyl] aminocarbonyl, (Ci-C 7) alkyl [(Ci-C7) - alkyl] aminocarbonyl, (Ci-C7) alkyl, [(CRC7) alkoxy] aminocarbonyl, ( C2-C7) -alkenylaminocarbonyl, (C3-C7) -cycloalkylaminocarbonyl,
Arylaminocarbonyl, Aryl-(Ci-C7)-alkylaminocarbonyl, Amino, (C1-C7)- Alkylamino, (C3-C7)-Cycloalkylamino, Bis[(Ci-C7)-Alkyl]amino steht, Arylaminocarbonyl, aryl- (C 1 -C 7) -alkylaminocarbonyl, amino, (C 1 -C 7) -alkylamino, (C 3 -C 7) -cycloalkylamino, bis [(C 1 -C 7) -alkyl] -amino,
R24, R25, R26, R28, R29 und R30 unabhängig voneinander für Wasserstoff, (C1-C7)- Alkyl, Halogen, (C3-C7)-Cycloalkyl, Aryl, Heteroaryl, Heterocyclyi, (C2-C7)- Alkenyl, (Ci-C7)-Alkoxy, (Ci-C7)-Alkoxy-(Ci-C7)-alkoxy, (Ci-C7)-Alkoxy- (Ci-C7)-alkyl, (Ci-C7)-Haloalkyl, (Ci-C7)-Alkylthio, (Ci-C7)-Haloalkylthio stehen,
A9 für O (Sauerstoff), S (Schwefel), N-H, N-CH3, N-OCH3 oder die Gruppierung CHR27 steht und wobei R27 in der Gruppierung CHR27 die Bedeutung gemäß der nachstehenden Definition hat und R 24 , R 25 , R 26 , R 28 , R 29 and R 30 independently of one another are hydrogen, (C 1 -C 7) -alkyl, halogen, (C 3 -C 7) -cycloalkyl, aryl, heteroaryl, heterocyclyl, (C 2 -C 7) C7) alkenyl, (C 1 -C 7 ) -alkoxy, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkoxy, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -alkylthio, (C 1 -C 7 ) -haloalkylthio, A 9 is O (oxygen), S (sulfur), NH, N-CH 3 , N-OCH 3 or the moiety CHR 27 and wherein R 27 in the moiety CHR 27 has the meaning as defined below and
R27 für Wasserstoff, Halogen, (Ci-C7)-Alkyl, Aryl, Heteroaryl, Heterocyclyl, R 27 represents hydrogen, halogen, (C 1 -C 7 ) -alkyl, aryl, heteroaryl, heterocyclyl,
(C3-C7)-Cycloalkyl, (C2-C7)-Alkenyl, (d-C7)-Alkoxy, (Ci-C7)-Alkoxy- (d-C7)-alkyl, Aryloxy-(Ci-C7)-alkyl, (d-C7)-Haloalkoxy, (Ci-C7)-Haloalkyl, (Ci-C7)-Alkylthio. (Ci-C7)-Haloalkylthio, Hydroxycarbonyl, (C1-C7)- Alkoxycarbonyl, (C3-C7)-Cycloalkoxycarbonyl, Aryl-(Ci-C7)- alkoxycarbonyl , (C2-C )-Alkenyloxycarbonyl , (C2-C7)-Al ki nyloxycarbonyl , Aminocarbonyl, (CrC )-Alkylaminocarbonyl, Bis[(Ci-C )- alkyl]aminocarbonyl, (Ci-C7)-Alkyl[(Ci-C7)-Alkyl]aminocarbonyl, (d-C )- Alkyl[(CrC7)-Alkoxy]aminocarbonyl, (C2-C7)-Alkenylaminocarbonyl, (C 3 -C 7) cycloalkyl, (C 2 -C 7) alkenyl, (dC 7) alkoxy, (Ci-C7) alkoxy (dC 7) alkyl, aryloxy (Ci-C 7 ) -alkyl, (dC 7 ) -haloalkoxy, (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -alkylthio. (C 1 -C 7 ) -haloalkylthio, hydroxycarbonyl, (C 1 -C 7 ) -alkoxycarbonyl, (C 3 -C 7 ) -cycloalkoxycarbonyl, aryl- (C 1 -C 7 ) -alkoxycarbonyl, (C 2 -C 4) -alkenyloxycarbonyl, (C 2 -C 4) -cycloalkoxycarbonyl, C 7 ) alkenyloxycarbonyl, aminocarbonyl, (C 1 -C 4) -alkylaminocarbonyl, bis [(C 1 -C 4 ) -alkyl] aminocarbonyl, (C 1 -C 7 ) -alkyl [(C 1 -C 7 ) -alkyl] aminocarbonyl, (dC ) - alkyl [(CrC 7 ) -alkoxy] aminocarbonyl, (C 2 -C 7 ) -alkenylaminocarbonyl,
(C3-C7)-Cycloalkylaminocarbonyl, Arylaminocarbonyl, Aryl-(Ci-C7)- alkylaminocarbonyl, Amino, (Ci-C7)-Alkylamino, (C3-C7)-Cycloalkylamino, Bis[(Ci-C7)-Alkyl]amino steht. (C 3 -C 7 ) -cycloalkylaminocarbonyl, arylaminocarbonyl, aryl- (C 1 -C 7 ) -alkylaminocarbonyl, amino, (C 1 -C 7 ) -alkylamino, (C 3 -C 7 ) -cycloalkylamino, bis [(C 1 -C 7 ) -Alkyl] amino.
13. Substituierte l -(Arylethinyl)-, 1 -(Heteroarylethinyl)-, l-(Heterocyclylethinyl)- und 1 -(Cyloalkenylethinyl)-cyclohexanole der allgemeinen Formel (I), oder deren Salze gemäß Anspruch 12, worin Substituted 1 - (arylethynyl) -, 1 - (heteroarylethynyl) -, l - (heterocyclylethynyl) - and 1 - (cycloalkenylethynyl) cyclohexanols of the general formula (I), or salts thereof according to claim 12, wherein
[X-Y] für die Gruppierung [X-Y] for grouping
[X-Y]1 steht, [XY] 1 stands,
Q für die Gruppierungen Q-1 bis Q-6 Q for the groupings Q-1 to Q-6
Q-1 Q-2 Q-3
Q-1 Q-2 Q-3
steht, wobei R7, R8, R9, R10, R11, R 2, R13, R14, R17, R18, R19, R20, R22, R23, R24, R25, R26, R28, R29 und R30 und A1 bis A9 jeweils die Bedeutung gemäß der nachstehenden Definitionen haben und wobei der Pfeil für eine Bindung zur jeweiligen Gruppierung C-R6 in der allgemeinen where R 7 , R 8 , R 9 , R 10 , R 11 , R 2 , R 13 , R 14 , R 17 , R 18 , R 19 , R 20 , R 22 , R 23 , R 24 , R 25 , R 26 , R 28 , R 29 and R 30 and A 1 to A 9 each have the meaning as defined below, and wherein the arrow for a bond to the respective group CR 6 in the general
Formel (I) steht, für (CrC6)-Alkyl, (C3-C6)-Cycloalkyl, (C4-C6)-Cycloalkenyl, (C2-C6)- Alkenyl, (C2-C6)-Alkinyl, (C2-C6)-Alkenyl-(Ci-C6)-alkyl, (C2-C6)-Alkinyl- (CrC6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, Hydroxy-(CrC6)-alkyl, (d-Ce)- Haloalkyl, (C2-C6)-Haloalkenyl, (C2-C6)-Haloalkinyl steht, Formula (I) represents (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, (C 4 -C 6 ) -cycloalkenyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) alkynyl, (C 2 -C 6) alkenyl (Ci-C 6) alkyl, (C 2 -C 6) alkynyl (CrC 6) alkyl, (Ci-C 6) alkoxy ( Ci-C 6) alkyl, hydroxy (CrC 6) alkyl, (d-Ce) - haloalkyl, (C 6) haloalkenyl, (C 2 -C 6) haloalkynyl is 2 -C,
R2, R3 und R4 unabhängig voneinander für Wasserstoff, Fluor, (Ci-C6)-Alkyl, (C3-C6)-Cycloalkyl, (C4-C6)-Cycloalkenyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl,R 2 , R 3 and R 4 independently of one another represent hydrogen, fluorine, (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, (C 4 -C 6 ) -cycloalkenyl, (C 2 -C 6 ) Alkenyl, (C 2 -C 6 ) alkynyl,
(C2-C6)-Alkenyl-(Ci-C6)-alkyl, (C2-C6)-Alkinyl-(Ci-C6)-alkyl, (Ci-C6)- Alkoxy-(Ci-C6)-alkyl, Hydroxy-(Ci-C6)-alkyl, (CrC6)-Haloalkyl stehen, für Hydroxy, (Ci-Cr,)-Alkoxy, Aryloxy, (Ca-CeJ-Cycloalkyloxy, (C2-Ce)- Alkenyloxy, (C2-C6)-Alkenyl-(Ci-C6)-alkyloxy, (Ci-C6)-Alkoxy-(Ci-C6)- alkyloxy, (Ci-C6)-Alkylcarbonyloxy, Arylcarbonyloxy, (C2-C6) alkenyl (Ci-C 6) alkyl, (C 2 -C 6) alkynyl (Ci-C 6) alkyl, (Ci-C6) - alkoxy- (Ci-C 6 ) -alkyl, hydroxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkyl, for hydroxy, (C 1 -C 8) -alkoxy, aryloxy, (C 1 -C 12 -cycloalkyloxy, (C 2 -Ce) - alkenyloxy, (C 2 -C 6) alkenyl (Ci-C 6) alkyloxy, (Ci-C6) alkoxy (Ci-C 6) - alkyloxy, (Ci-C6) alkylcarbonyloxy, arylcarbonyloxy,
Heteroarylcarbonyloxy, (Ca-Cr^-Cycloalkylcarbonyloxy, (Ci-Ce)- Alkoxycarbonyloxy, (C2-C6)-Alkenyloxycarbonyloxy, Aryloxy-(Ci-Ce)- alkyloxy, Aryl-(Ci-C6)-alkyloxy, (Ci-C6)-Alkoxy-(Ci-C6)-alkoxy-(Ci-C6)- alkyloxy, (Ci-C6)-Alkylthio-(Ci-C6)-alkyloxy, Tris[(Ci-C6)-alkyl]silyloxy, (Ci-C6)-Alkyl-Bis[(Ci-C6)-alkyl]silyloxy, (Ci-C6)-Alkyl-bis(Aryl)silyloxy, Aryl-bis[(Ci-C6)— alkyljsilyloxy, Cycloalkyl-bis[(Ci-C6)-alkyl]silyloxy, Halo- bis[(Ci-C6)-alkyl]silyloxy, Tris[(Ci-C6)-alkyl]silyl-(Ci-C6)-alkoxy-(Ci-C6)- alkyloxy steht,
für (Ci-Ce)- Alkylsulfonylaminocarbonyl, (Ca-Ce)-Heteroarylcarbonyloxy, (Ca-Cr ^ -cycloalkylcarbonyloxy, (Ci-Ce) -alkoxycarbonyloxy, (C 2 -C 6) -alkenyloxycarbonyloxy, aryloxy- (Ci-Ce) -alkyloxy, aryl- (Ci-C 6 ) -alkyloxy, (Ci -C 6 ) -alkoxy- (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyloxy, (C 1 -C 6 ) -alkylthio (C 1 -C 6 ) -alkyloxy, tris [(C 1 -C 6 ) alkyl] silyloxy, (C 1 -C 6 ) -alkyl-bis [(C 1 -C 6 ) -alkyl] silyloxy, (C 1 -C 6 ) -alkyl bis (aryl) silyloxy, aryl-bis [(Ci-C 6) - alkyljsilyloxy, cycloalkyl-bis silyloxy [(Ci-C 6) alkyl], halo silyloxy bis [(Ci-C 6) alkyl], tris [(Ci-C6) alkyl] silyl (Ci- C 6 ) alkoxy- (C 1 -C 6 ) -alkyloxy, for (C 1 -C 6) -alkylsulfonylaminocarbonyl, (Ca-Ce) -
Cycloalkylsulfonylaminocarbonyl, Hydroxycarbonyl, (d-Ce)- Alkoxycarbonyl, (Ca-CeJ-Cycloalkoxycarbonyl, (C3-C6)-Cycloalkyl-(Ci-C6)- alkoxycarbonyl, Aryloxycarbonyl, Aryl-(d-C6)-alkoxycarbonyl, (d-d,)- Alkenyloxycarbonyl, (C-2-C6)-Alkinyloxycarbonyl, (d-Ce)- Haloalkyloxycarbonyl, (Ci-C6)-Alkoxy-(Ci-Ce)-alkoxycarbonyl, (d-d)- Alkenyloxy-(CrC6)-alkoxycarbonyl, (Ci-Cc>)-Alkylamino-(Ci-C6)- alkoxycarbonyl, Tris[(CrC6)-alkyl]silyloxy-(Ci-C6)-alkoxycarbonyl, Bis[(Ci-Cö)-Alkyl]amino-(Ci-C6)-alkoxycarbonyl, (Ci-d)-Alkyl[(Ci-C6)- alkyl]amino-(Ci-C6)-alkoxycarbonyl, Cyano-(Ci-C6)-alkoxycarbonyl, Heterocyclyl-N-(Ci-C6)-alkoxycarbonyl, Heteroaryloxycarbonyl, Cycloalkylsulfonylaminocarbonyl, hydroxycarbonyl, (d-Ce) -alkoxycarbonyl, (Ca-CeJ-cycloalkoxycarbonyl, (C3-C6) -cycloalkyl- (Ci-C6) -alkoxycarbonyl, aryloxycarbonyl, aryl- (d-C6) -alkoxycarbonyl, (dd, ) - alkenyloxycarbonyl, (C-2-C6) -alkynyloxycarbonyl, (d-Ce) - haloalkyloxycarbonyl, (Ci-C6) -alkoxy- (Ci-Ce) -alkoxycarbonyl, (dd) -alkenyloxy- (CrC6) -alkoxycarbonyl, (Ci-Cc>) - alkylamino- (Ci-C6) - alkoxycarbonyl, tris [(CrC6) -alkyl] silyloxy- (Ci-C6) -alkoxycarbonyl, bis [(Ci-Cö) -alkyl] amino- (C C 6) -alkoxycarbonyl, (C 1 -d) -alkyl [(C 1 -C 6) -alkyl] amino- (C 1 -C 6) -alkoxycarbonyl, cyano- (C 1 -C 6) -alkoxycarbonyl, heterocyclyl-N- (C 1 -C 6) alkoxycarbonyl, heteroaryloxycarbonyl,
Heteroaryl-(CrC6)-alkoxycarbonyl, Heterocyclyl-(Ci-C6)-alkoxycarbonyl, Heterocyclyloxycarbonyl, (C2-C6)-Alkenyl-(d-C6)-alkoxycarbonyl, (C2-C6)-Alkinyl-(Ci-C6)-alkoxycarbonyl, Aryl-(C2-Cc>)-alkinyloxycarbonyl, Aryl-(C2-Cr,)-alkenyloxycarbonyi, Aminocarbonyl, (Ci-d)- Alkylaminocarbonyl, Bis[(CrC6)-alkyl]aminocarbonyl, (d-d)- Alkyl[(Ci-C6)-Alkyl]aminocarbonyl, (Ci-C6)-Alkyl[(Ci-C6)- Alkoxy]aminocarbonyl, (C2-C6)-Alkenylaminocarbonyl, (Ca-Ce)- Cycloalkylaminocarbonyl, Arylaminocarbonyl, Aryl-(Ci-C6)- alkylaminocarbonyl, Heteroaryl-(Ci-C6)-alkylaminocarbonyl, Cyano- (Ci-C6)-alkylaminocarbonyl, (Ci-C6)-Haloalkylaminocarbonyl, (C2-d)- Alkinyl-(Ci-C6)-alkylaminocarbonyl, (Ci-Ce)- Alkoxycarbonylaminocarbonyl, Aryl-(Ci-d)- alkoxycarbonylaminocarbonyl, Hydroxycarbonyl-(CrC6)-alkyl, (d-d)- Alkoxycarbonyl-(Ci-C6)-alkyl, (C3-C6)-Cycloalkoxycarbonyl-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkoxycarbonyl-(Ci-C6)-alkyl, (d-d)- Alkenyloxycarbonyi-(Ci-Cö)-alkyl, Aryl-(Ci-C6)-alkoxycarbonyl-(Ci-C6)- alkyl, (Ci-C6)-Alkylaminocarbonyl-(Ci-C6)-alkyl, Aminocarbonyl-(Ci-C6)- alkyl, Bis[(Ci-C6)-alkyl]aminocarbonyl-(Ci-C6)-alkyl, (d-d)- Cycloalkylaminocarbonyl-(Ci-C6)-alkyl, Aryl-(Ci-C6)-alkylaminocarbonyl- (d-C6)-alkyl, Heteroaryl-(Ci-C6)-alkylaminocarbonyl-(Ci-C6)-alkyl, Cyano-(Ci-C6)-alkylaminocarbonyl-(d-C6)-alkyl, (d-d)- Haloalkylaminocarbony!-(Ci-C6)-alkyl, (d-d -AlkinyKCi-d)- alkylaminocarbonyl-(Ci-C6)-alkyL (C3-Cf,)-Cycloalkyl-(Ci-C6)-
alkylaminocarbonyl-(Ci-C6)-alkyl, (Ci-C6)-Alkoxycarbonylaminocarbonyl- (Ci-C6)-alkyl, Aryl-(d-C6)-alkoxycarbonylaminocarbonyi-(Ci-C6)-alkyl, (CrC6)-Alkoxycarbonyl-(Ci-C6)-alkylaminocarbonyl, Hydroxycarbonyl- (CrCö)-alkylaminocarbonyl, Aryl-(Ci-C6)-alkoxycarbonyl-(Ci-Cc>)- alkylaminocarbonyl, Aminosulfonyl, (Ci-d -Alkoxycarbonyl-heterocyclyl- N-carbonyl, (CrC6)-Alkoxycarbonyl-(Ci-C6)-alkyl- heterocyclylidenaminocarbonyl, (d-Ce AIkoxycarbonylheterocyclyliden- (Ci-C6)-alkylaminocarbonyl (Ci-C6)-Alkoxycarbonyl-(Ci-C6)-Alkyl((Ci-C6)- alkyl)aminocarbonyl, (Ci-C6)-Alkoxycarbonyl-(C3-C6)- cycloalkylidenaminocarbonyl, Heterocyclyl-N-carbonyl, (Ci-C6)-Alkoxy- (d-Ce alkylaminocarbonyl, Aminocarbonyl-(Ci-C6)-alkylaminocarbonyl, (Ci-C6)-Alkylaminocarbonyl-(Ci-C6)-alkylaminocarbonyl, Heteroaryl- (C 1 -C 6) -alkoxycarbonyl, heterocyclyl- (C 1 -C 6) -alkoxycarbonyl, heterocyclyloxycarbonyl, (C 2 -C 6) -alkenyl- (C 1 -C 6) -alkoxycarbonyl, (C 2 -C 6) -alkynyl- (C 1 -C 6) - alkoxycarbonyl, aryl (C2-Cc>) alkynyloxycarbonyl, aryl (C2-Cr,) - alkenyloxycarbonyi, aminocarbonyl, (Ci-d) - alkylaminocarbonyl, bis [(CRC6) alkyl] aminocarbonyl, (dd) - alkyl [ (Ci-C 6) alkyl] aminocarbonyl, (Ci-C6) alkyl [(Ci-C6) - alkoxy] aminocarbonyl, (C2-C6) -Alkenylaminocarbonyl, (Ca-Ce) - cycloalkylaminocarbonyl, arylaminocarbonyl, aryl - (C 1 -C 6) -alkylaminocarbonyl, heteroaryl- (C 1 -C 6) -alkylaminocarbonyl, cyano- (C 1 -C 6) -alkylaminocarbonyl, (C 1 -C 6) -haloalkylaminocarbonyl, (C 2 -C 4) -alkynyl- (C 1 -C 6) -alkylaminocarbonyl, (Ci-Ce) - alkoxycarbonylaminocarbonyl, aryl- (Ci-d) - alkoxycarbonylaminocarbonyl, hydroxycarbonyl- (CrC6) -alkyl, (dd) - alkoxycarbonyl- (Ci-C6) -alkyl, (C3-C6) -cycloalkoxycarbonyl (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkoxycarbonyl- (C 1 -C 6 ) -alkyl, (dd) -alkenyloxycarbonyi (C 1 -C 6) -alkyl, aryl- (Ci-C6) alkoxycarbonyl (Ci C 6 ) -alkyl, (C 1 -C 6 ) -alkylaminocarbonyl- (C 1 -C 6 ) -alkyl, aminocarbonyl- (C 1 -C 6 ) -alkyl, bis [(C 1 -C 6 ) -alkyl] aminocarbonyl- (C 1 -C 6 ) - alkyl, (dd) - cycloalkylaminocarbonyl- (C 1 -C 6) -alkyl, aryl- (C 1 -C 6) -alkylaminocarbonyl- (C 1 -C 6) -alkyl, heteroaryl- (C 1 -C 6) -alkylaminocarbonyl- (C 1 -C 6) - alkyl, cyano- (Ci-C6) -alkylaminocarbonyl- (d-C6) -alkyl, (dd) - Haloalkylaminocarbony! - (Ci-C 6 ) -alkyl, (dd -AlkinyKCi-d) - alkylaminocarbonyl- (Ci-C6 ) -alkyL (C3-Cf,) - cycloalkyl- (Ci-C6) - alkylaminocarbonyl- (C 1 -C 6) -alkyl, (C 1 -C 6) -alkoxycarbonylaminocarbonyl- (C 1 -C 6) -alkyl, aryl- (C 1 -C 6) -alkoxycarbonylaminocarbonyl- (C 1 -C 6) -alkyl, (C 1 -C 6) -alkoxycarbonyl- (C 1 -C 6) -alkylaminocarbonyl, hydroxycarbonyl- (C 1 -C 6) -alkylaminocarbonyl, aryl- (C 1 -C 6) -alkoxycarbonyl- (C 1 -C 4 -cyclo) -alkylaminocarbonyl, aminosulfonyl, (C 1 -C 4 -alkoxycarbonyl-heterocyclyl-N-carbonyl, (C 1 -C 6 ) -alkoxycarbonyl- (C 1 -C 6 ) -alkyl-heterocyclylideneaminocarbonyl, (C 1 -C 6 -alkoxycarbonylheterocyclylidene- (C 1 -C 6 ) -alkylaminocarbonyl (C 1 -C 6 ) -alkoxycarbonyl- (C 1 -C 6 ) -alkyl ((Ci -C 6) -alkyl) aminocarbonyl, (C 1 -C 6) -alkoxycarbonyl- (C 3 -C 6) -cycloalkylideneaminocarbonyl, heterocyclyl-N-carbonyl, (C 1 -C 6) -alkoxy- (C 1 -C 6 -alkylaminocarbonyl, aminocarbonyl- (C 1 -C 6) -cycloalkylideneaminocarbonyl; ) -alkylaminocarbonyl, (C 1 -C 6) -alkylaminocarbonyl- (C 1 -C 6) -alkylaminocarbonyl,
(C3-C6)-Cycloalky!aminocarbonyl-(Ci-C6)-alkylaminocarbonyl, (Ca-Ce)- Cycloalkyl-(Ci-Cö)-alkylaminocarbonyl, (C3-C6)-Cycloalkyl-(CrC6)- alkylaminocarbonyl-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl-(d-C6)- alkylaminocarbonyl-(Ci-C6)-alkylaminocarbonyl, (C2-C6)-Alkenyl-(Ci-Cö)- alkylaminocarbonyl, (C2-C6)-Alkenylaminocarbonyl-(CrC6)-alkyl, (d-Ce)- Alkenyl-(Ci-C6)-alkylaminocarbonyl-(Ci-C6)-alkyl, (Ci-C6)-Alkylcarbonyl, (C3-C6)-Cycloalkylcarbonyl, Aryicarbonyi, Formyl, Hydroxyiminomethyl, Aminoiminomethyl, (Ci-C6)-Alkoxyiminomethyl, (Ci-Ce)- Alkylaminoiminomethyl, Bis[(Ci-C6)-alkyl]aminoiminomethyl, (Ca-Co)- Cycloalkoxyiminomethyl, (d C6)-Cycloalkyl-(d-C6)-alkoximinomethyl, Aryloximinomethyl, Aryl-(Ci-C6)-alkoxyiminomethyl, Aryl-(d-C6)- alkylaminoiminomethyl, (C2-C6)-Alkenyloxyiminomethyl, (C 3 -C 6) -cycloalkyl-aminocarbonyl- (C 1 -C 6) -alkylaminocarbonyl, (Ca-Ce) -cycloalkyl- (C 1 -C 6) -alkylaminocarbonyl, (C 3 -C 6) -cycloalkyl- (C 1 -C 6) -alkylaminocarbonyl- (Ci -C 6) -alkyl, (C 3 -C 6) -cycloalkyl- (C 1 -C 6) -alkylaminocarbonyl- (C 1 -C 6) -alkylaminocarbonyl, (C 2 -C 6) -alkenyl- (C 1 -C 6) -alkylaminocarbonyl, (C 2 -C 6 ) Alkenylaminocarbonyl- (C 1 -C 6) -alkyl, (C 1 -C 6) -alkenyl- (C 1 -C 6) -alkylaminocarbonyl- (C 1 -C 6) -alkyl, (C 1 -C 6) -alkylcarbonyl, (C 3 -C 6) -cycloalkylcarbonyl, Aryicarbonyi, formyl, hydroxyiminomethyl, aminoiminomethyl, (C 1 -C 6) -alkoxyiminomethyl, (C 1 -C 6) -alkylaminoiminomethyl, bis [(C 1 -C 6) -alkyl] aminoiminomethyl, (Ca-Co) -cycloalkoxyiminomethyl, (C 1 -C 6) -cycloalkyl - (C 1 -C 6) -alkoximinomethyl, aryloximinomethyl, aryl- (C 1 -C 6) -alkoxyiminomethyl, aryl- (C 1 -C 6) -alkylaminoiminomethyl, (C 2 -C 6) -alkenyloxyiminomethyl,
Arylaminoiminomethyl, Arylsulfonylaminoiminomethyl, Arylaminoiminomethyl, arylsulfonylaminoiminomethyl,
Hydroxyaminocarbonyl, (Crd -Alkoxyaminocarbonyl, Aryl-(Ci-C-6)- alkoxyaminocarbonyl steht, Hydroxyaminocarbonyl, (C 1-6 -alkoxyaminocarbonyl, aryl- (C 1 -C 6) -alkoxyaminocarbonyl,
R7, R8 , R9 und R0 unabhängig voneinander für Wasserstoff, Fluor, Chlor, Brom, lod, Nitro, Amino, Cyano,
gegebenenfalls R 7 , R 8 , R 9 and R 0 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, nitro, amino, cyano, possibly
substituiertes Phenyl, Heteroaryl, (Ca-d -Cycloalkyl, (C4-Ce)- Cycloalkenyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (C2-C6)-Alkenyl-(Ci-C6)- alkyl, (C2-C6)-Alkinyl-(Ci-C6)-alkyl, Hydroxy, (Ci-C6)-Alkoxy, (Ci-C6)- Alkoxy-(Ci-C6)-alkoxy, (Ci-Ce)-Alkoxy-(Ci-C6)-alkyl, Hydroxy-(Ci-Cc)-
alkyl, (Ci-Ce)-Haloalkoxy, (Ci-C6)-Haloalkyl, (C2-C6)-Haloalkenyl, (d-Ce)- Haloalkinyl, (Ci-C6)-Haloalkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)- haloalkyl, (Ci-C6)-Haloalkoxy-(Ci-C6)-haloalkyl, Hydrothio, (CrC6)- Alkylthio, (Ci-C6)-Haloalkylthio, (Ci-C6)-Alkylihio-(Ci-C6)-alkyl, (Ci-C6)- Haloalkylthio-(Ci-C6)-alkyl, (Ci-C6)-Alkylamino, Bis[(Ci-C6)-alkyl]amino, (C2-C6)-Alkenylamino, (Ca-Cr -Cycloalkylamino, (d-Ce)- Alkylcarbonylamino, (C3-C6)-Cycloalkylcarbonylamino, substituted phenyl, heteroaryl, (Ca-d-cycloalkyl, (C 4 -Ce) - cycloalkenyl, (C2-C6) alkenyl, (C 2 -C 6) -alkynyl, (C2-C6) alkenyl ( Ci-C 6) - alkyl, (C2-C6) alkynyl (Ci-C 6) alkyl, hydroxy, (Ci-C 6) alkoxy, (Ci-C6) - alkoxy- (Ci-C 6 ) -alkoxy, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, hydroxy- (C 1 -C 4) - alkyl, (C 1 -C 6 ) -haloalkoxy, (C 1 -C 6 ) -haloalkyl, (C 2 -C 6 ) -haloalkenyl, (d-Ce) -haloalkynyl, (C 1 -C 6 ) -haloalkoxy- (C 1 -C 6 ) alkyl, (Ci-C6) alkoxy (Ci-C 6) - haloalkyl, (Ci-C 6) haloalkoxy (Ci-C6) -haloalkyl, Hydrothio, (CrC 6) - alkylthio, (C -C 6) haloalkylthio, (Ci-C 6) -Alkylihio- (Ci-C 6) alkyl, (Ci-C 6) - Haloalkylthio- (Ci-C 6) alkyl, (Ci-C 6) - Alkylamino, bis [(C 1 -C 6 ) -alkyl] amino, (C 2 -C 6 ) -alkenylamino, (C 1 -C 6 -cycloalkylamino, (C 1 -C 6 ) -alkylcarbonylamino, (C 3 -C 6 ) -cycloalkylcarbonylamino,
Arylcarbonylamino, Heteroarylcarbonylamino, Formylamino, (d-Ce)- Haloalkylcarbonylamino, (Ci-C6)-Alkoxycarbonylamino, (Ci-Cr>)- Alkylaminocarbonylamino, (Ci-C6)-Alkyl[(Ci-C6)- Alkyl]aminocarbonylamino, (CrCr -Alkylsulfonylamino, (Ca-Ce)- Cycloalkylsulfonylamino, Arylsulfonylamino, Hetarylsulfonylamino, Sulfonyl-(Ci-C6)-haloalkylamino, Amino-(Ci-Cc>)-alkylsulfonyl, Amino- (Ci-C6)-haloalkylsulfonyl, (Ci-C6)-Alkylaminosulfonyl, Bis[(CrC6)- alkyljaminosulfonyl, (Ca-CeJ-Cycloalkylaminosulfonyl, (d-Ce)- Haloalkylaminosulfonyl, Heteroarylaminosulfonyl, Arylaminosulfonyl, Aryl- (Ci-C6)-alkylaminosulfonyl, (Ci-C6)-Alkylsulfonyl, (C3-C6)- Cycloalkylsulfonyl, Arylsulfonyl, HydroxycarbonyL (Ci-Ce)- Alkoxycarbonyl, (Ca-CeJ-Cycloalkoxycarbonyl, (C3-C6)-Cycloalkyl-(Ci-Cr>)- alkoxycarbonyl, Aryloxycarbonyl, Aryl-(Ci-Ce)-alkoxycarbonyl, (C2-Ce)- Alkenyloxycarbonyl, (C2-C6)-Alkinyloxycarbonyl, Aminocarbonyl, (d-Ce)- Alkylaminocarbonyl, Bis[(Ci-C6)-alkyl]aminocarbonyl, (Ci-Ce)- Alkyl[(Ci-C6)-Alkyl]aminocarbonyl, (Ci-C6)-Alkyl[(Ci-C6)- Alkoxy]aminocarbonyl, (C2-C6)-Alkenylaminocarbonyl, (C3-Ce)- Cycloalkylaminocarbonyl, Arylaminocarbonyl, Aryl-(Ci-C6)- alkylaminocarbonyl stehen, Arylcarbonylamino, heteroarylcarbonylamino, formylamino, (d-Ce) - haloalkylcarbonylamino, (Ci-C6) -alkoxycarbonylamino, (Ci-Cr > ) - alkylaminocarbonylamino, (Ci-C6) -alkyl [(Ci-C6) - alkyl] aminocarbonylamino, ( CrCr-alkylsulfonylamino, (Ca-Ce) -cycloalkylsulfonylamino, arylsulfonylamino, hetarylsulfonylamino, sulfonyl- (Ci-C6) -haloalkylamino, amino- (Ci-Cc > ) -alkylsulfonyl, amino- (Ci-C 6 ) -haloalkylsulfonyl, (Ci -C 6) alkylaminosulfonyl, bis [(CrC 6) - alkyljaminosulfonyl, (Ca-CeJ-Cycloalkylaminosulfonyl, (d-Ce) - Haloalkylaminosulfonyl, heteroarylaminosulfonyl, arylaminosulfonyl, aryl (Ci-C6) alkylaminosulfonyl, (Ci-C 6) alkylsulfonyl, (C 3 -C 6) - cycloalkylsulfonyl, arylsulfonyl, hydroxycarbonyl (Ci-Ce) - alkoxycarbonyl, (Ca-CeJ-cycloalkoxycarbonyl, (C3-C6) cycloalkyl (Ci-Cr>) - alkoxycarbonyl, Aryloxycarbonyl, aryl- (Ci-Ce) -alkoxycarbonyl, (C2-Ce) -alkenyloxycarbonyl, (C2-C6) -alkynyloxycarbonyl, aminocarbonyl, (d-Ce) -alkylaminocarbonyl, bis [(Ci-C6) -alkyl] aminocarbonyl, (Ci-Ce) - Alkyl (Ci-C 6) alkyl] aminocarbonyl, (Ci-C6) alkyl [(Ci-C6) - alkoxy] aminocarbonyl, (C2-C6) -Alkenylaminocarbonyl, (C3-Ce) - cycloalkylaminocarbonyl, arylaminocarbonyl, aryl - (C 1 -C 6) -alkylaminocarbonyl,
A1 , A2, A3 und A4 gleich oder verschieden sind und unabhängig voneinander für N (Stickstoff) oder die Gruppierungen C-H, C-CH3, C-F, C-Cl, C-Br, C-l, C-OCF3, C-OCH3, C-CF3, C-CO2H, C-CO2CH3 stehen, wobei jedoch in keinem Fall mehr als zwei N -Atome benachbart sind, A 1 , A 2 , A 3 and A 4 are the same or different and are each independently N (nitrogen) or the groupings CH, C-CH 3 , CF, C-Cl, C-Br, Cl, C-OCF 3, C -OCH 3, C-CF 3, C-CO2H, C-CO2CH3 are, but in no case more than two N -atoms are adjacent,
R1 1 und R12 unabhängig voneinander für Wasserstoff, Fluor, Chlor, Brom, lod, (Ci-C6)-Alkyl, gegebenenfalls substituiertes Phenyl, Heteroaryl,
Heterocyclyl, (C3-C6)-Cycloalkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (Ci-Ce)- Alkoxy-(Ci-C6)-alkyl, Aryloxy-(Ci-C6)-alkyl, (Ci-C6)-Haloalkyl, (CrC6)- Haloalkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)- aloalkyl, (d-Ce)- Haloalkoxy-(Ci-C6)-haloalkyl, (Ci-C6)-Alkylthio-(Ci-C6)-alkyl, R 1 1 and R 12 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, (Ci-C6) alkyl, optionally substituted phenyl, heteroaryl, Heterocyclyl, (C 3 -C 6 ) -cycloalkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, aryloxy- (Ci -C 6) alkyl, (Ci-C 6) -haloalkyl, (CrC 6) - haloalkoxy (Ci-C 6) alkyl, (Ci-C6) alkoxy (Ci-C 6) - aloalkyl, (d-Ce) - haloalkoxy- (C 1 -C 6 ) -haloalkyl, (C 1 -C 6 ) -alkylthio (C 1 -C 6 ) -alkyl,
Hydroxycarbonyl, (Ci-CeJ-Alkoxycarbonyl, (Ca-CeJ-Cycloalkoxycarbonyl, (C3-C6)-Cycloalkyl-(Ci-Cr>)-alkoxycarbonyl, Aryloxycarbonyl, Aryl-(Ci-Ce)- al koxycarbonyl , (C2-C6)-Alkenyloxycarbonyl , (C2-Ce)-Al ki nyloxycarbonyl , Aminocarbonyl, (Ci-Cr -Alkylaminocarbonyl, Bis[(Ci-Ce)- alkyl]aminocarbonyl, (Ci-C6)-Alkyl[(Ci-C6)-Alkyl]aminocarbonyl, (Ci-Ce)- Alkyl[(Ci-C6)-Alkoxy]aminocarbonyl, (C2-C6)-Alkenylaminocarbonyl, (Ca-Cr -Cycloalkylaminocarbonyl, Arylaminocarbonyl, Aryl-(Ci-Ce)- alkylaminocarbonyl stehen, Hydroxycarbonyl, (Ci-CeJ-alkoxy, (Ca-CeJ-cycloalkoxycarbonyl, (C3-C6) cycloalkyl (Ci-Cr>) -alkoxycarbonyl, aryloxycarbonyl, aryl (Ci-Ce) - al koxycarbonyl, (C2-C6 ) Alkenyloxycarbonyl, (C 2 -C 6) -alkyloxycarbonyl, aminocarbonyl, (C 1 -C 6 -alkylaminocarbonyl, bis [(C 1 -C 6) -alkyl] aminocarbonyl, (C 1 -C 6) -alkyl [(C 1 -C 6) -alkyl ] aminocarbonyl, (C 1 -C 6) -alkyl [(C 1 -C 6) -alkoxy] -aminocarbonyl, (C 2 -C 6) -alkenylaminocarbonyl, (C 1 -C 6 -cycloalkylaminocarbonyl, arylaminocarbonyl, aryl- (C 1 -C 6) -alkylaminocarbonyl,
A5 für S (Schwefel), O (Sauerstoff) oder die Gruppierungen N-H, N-CH3, N- CH2CH3, N-CH(CH3)2, N-C02t-Bu, N-Aryl, N-Heteroaryl, N-Heterocyclyl steht. A 5 represents S (sulfur), O (oxygen) or the groupings NH, N-CH 3 , N-CH 2 CH 3 , N-CH (CH 3 ) 2 , N-CO 2 t-Bu, N-aryl, N-heteroaryl, N-heterocyclyl is.
R13, R14, R17 und R18 unabhängig voneinander für Wasserstoff, (Ci-CeJ-Alkyl, Fluor, Chlor, Brom, lod, (Ca-CeJ-Cycloalkyl, gegebenenfalls substituiertes Phenyl, Heteroaryl, Heterocyclyl, (C2-Ce)-Alkenyl, Aryl-(Ci-C6)-alkyl, (CrC6)-Alkoxy, (Ci-C6)-Alkoxy-(Ci-C6)-alkoxy, (Ci-C6)-Alkoxy-(Ci-C6)- alkyl, Hydroxy, (d-CeJ-Haloalkyl, (Ci-C6)-Haloalkylthio stehen oder R 13 , R 14 , R 17 and R 18 independently of one another are hydrogen, (C 1 -C 6 -alkyl, fluorine, chlorine, bromine, iodine, (C 1 -C 6 -cycloalkyl, optionally substituted phenyl, heteroaryl, heterocyclyl, (C 2 -C 6) ) Alkenyl, aryl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkoxy- (Ci -C 6 ) - alkyl, hydroxy, (d-CeJ-haloalkyl, (Ci-C6) -haloalkylthio or
R13 und R17 mit den Atomen, an die sie gebunden sind, einen vollständig R 13 and R 17 complete with the atoms to which they are attached
gesättigten oder teilgesättigten, gegebenenfalls weiter substituierten 5 bis 7-gliedrigen Ring bilden, form a saturated or partially saturated, optionally further substituted 5 to 7-membered ring,
A6, A7 gleich oder verschieden sind und unabhängig voneinander für O A 6 , A 7 are the same or different and are each independently O.
(Sauerstoff), S (Schwefel), N-H, N-OCH3, N-CH3 oder die Gruppierung CR15R16 stehen, wobei jedoch in keinem Fall zwei N-, O- oder S-Atome benachbart sind, und wobei R15 und R16 in der Gruppierung CR15R16 jeweils gleiche oder verschiedene Bedeutungen gemäß der (Oxygen), S (sulfur), NH, N-OCH3, N-CH 3 or the group CR 15 R 16, but in no case two N, O or S atoms are adjacent, and wherein R 15 and R 16 in the group CR 15 R 16 each have the same or different meanings according to the
nachstehenden Definition haben und
R15 und R16 unabhängig voneinander für Wasserstoff, Fluor, Chlor, Brom, lod, (Ci-C-6)-Alkyl, gegebenenfalls substituiertes Phenyl, Heteroaryl, have the following definition and R 15 and R 16 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, (C 1 -C 6) -alkyl, optionally substituted phenyl, heteroaryl,
Heterocyclyl, (C3-C6)-Cycloalkyl, (C2-C6)-Alkenyl, (Ci-Ce)-Alkoxy, (Ci-C6)- Alkoxy-(CrC6)-alkyl, (Ci-C6)-Haloalkoxy, (Ci-C6)-Haloalkyl, (d-C6)- Alkylthio, (CrC6)-Haloalkylthio, (Ci-C6)-Alkylthio-(Ci-C6)-alkyl, Heterocyclyl, (C 3 -C 6) -cycloalkyl, (C 2 -C 6) alkenyl, (Ci-Ce) alkoxy, (Ci-C6) - alkoxy (CrC 6) alkyl, (Ci-C 6) haloalkoxy, (Ci-C 6) -haloalkyl, (dC 6) - alkylthio, (CrC 6) haloalkylthio, (Ci-C 6) alkylthio (Ci-C 6) alkyl,
Hydroxycarbonyl, (Ci-CeJ-Alkoxycarbonyl, (C3-C6)-Cycloalkoxycarbonyl, Aryl-(d-C6)-alkoxycarbonyl, (C2-C6)-Alkenyloxycarbonyl, Aminocarbonyl, (Ci-CeJ-Alkylaminocarbonyl, Bis[(CrC6)-alkyl]aminocarbonyl, (Ci-Ce)- Alkyl[(Ci-Cö)-Alkyl]aminocarbonyl, (C2-C6)-Alkenylaminocarbonyl, (C:3-C6)-Cycloalkylaminocarbonyl, Aryl-(Ci-C6)-alkylaminocarbonyl, Amino, (Ci-C6)-Alkylamino, (C3-C6)-Cycloalkylamino, Bis-[(d-C6)- Alkyl]amino stehen, Hydroxycarbonyl, (C 1 -C 6) -alkoxycarbonyl, (C 3 -C 6) -cycloalkoxycarbonyl, aryl- (C 1 -C 6) -alkoxycarbonyl, (C 2 -C 6) -alkenyloxycarbonyl, aminocarbonyl, (C 1 -C 6 -alkylaminocarbonyl, bis [(C 1 -C 6) - alkyl] aminocarbonyl, (C 1 -C 6) -alkyl [(C 1 -C 6) -alkyl] aminocarbonyl, (C 2 -C 6) -alkenylaminocarbonyl, (C 3 -C 6) -cycloalkylaminocarbonyl, aryl- (C 1 -C 6) -alkylaminocarbonyl, Amino, (C 1 -C 6) -alkylamino, (C 3 -C 6) -cycloalkylamino, bis - [(C 1 -C 6) -alkyl] -amino,
R19, R20, R22 und R23 unabhängig voneinander für Wasserstoff, (Ci-Ce)-Alkyl,R 19 , R 20 , R 22 and R 23 independently of one another represent hydrogen, (C 1 -C 6) -alkyl,
Fluor, Chlor, Brom, lod, (Ca-CeJ-Cycloalkyl, Aryl, Heteroaryl, Heterocyclyl, (C2-C6)-Alkenyl, Aryl-(Ci-C6)-alkyl, (Ci-Ce)-Alkoxy, (Ci-C6)-Haloalkyl stehen, Fluorine, chlorine, bromine, iodine, (Ca-CeJ-cycloalkyl, aryl, heteroaryl, heterocyclyl, (C 2 -C 6) alkenyl, aryl (Ci-C 6) alkyl, (Ci-Ce) alkoxy, (C 1 -C 6 ) -haloalkyl,
A8 für O (Sauerstoff), S (Schwefel), N-H, N-CH3, N-OCH3 oder die Gruppierung CHR21 steht und wobei R21 in der Gruppierung CHR21 die Bedeutung gemäß der nachstehenden Definition hat, A 8 is O (oxygen), S (sulfur), NH, N-CH 3 , N-OCH 3 or the moiety CHR 21 , and wherein R 21 in the moiety CHR 21 has the meaning as defined below,
R21 für Wasserstoff, Fluor, Chlor, Brom, lod, (Ci-Ce)-Alkyl, gegebenenfalls R 21 is hydrogen, fluorine, chlorine, bromine, iodine, (C 1 -C 6) -alkyl, if appropriate
substituiertes Phenyl, Heteroaryl, Heterocyclyl, (C3-C6)-Cycloalkyl, substituted phenyl, heteroaryl, heterocyclyl, (C 3 -C 6) -cycloalkyl,
(C2-C6)-Alkenyl, (Ci-Ce)-Alkoxy, (Ci-C6)-Haloalkoxy, (Ci-C6)-Haloalkyl, (Ci-Cc)-Alkylthio, (Ci-C6)-Haloalkylthio, Hydroxycarbonyl, Aryl-(Ci-Ce)- alkoxycarbonyl, (C2-Cc>)-Alkenyloxycarbonyl, Aminocarbonyl, (Ci-Ce)- Alkylaminocarbonyl, Bis[(Ci-C6)-alkyl]aminocarbonyl, (Ci-Ce)- Alkyl[(Ci-C6)-Alkyl]aminocarbonyl, (Ci-C6)-Alkyl[(Ci-C6)- Alkoxyjaminocarbonyl, (C2-Cc>)-Alkenylaminocarbonyl, (C3-C6)- Cycloalkylaminocarbonyl, Aryl-(Ci-C6)-alkylaminocarbonyl, Amino, (d-C6)-Alkylamino, (Ca-Cr -Cycloalkylamino, Bis[(d-C6)-Alkyl]amino steht,
R24, R25, R26, R28, R29 und R30 unabhängig voneinander für Wasserstoff, (Ci-Ce)- Alkyl, Fluor, Chlor, Brom, lod, (Cs-Cc -Cycloalkyl, Aryl, Heteroaryl, Heterocyclyl, (C2-C6)-Alkenyl, (Ci-C6)-Alkoxy, (Ci-C6)-Haloalkyl, (Ci-Ce)- Alkylthio, (CrCeJ-Haloalkylthio stehen, (C 2 -C 6) alkenyl, (Ci-Ce) alkoxy, (Ci-C 6) -haloalkoxy, (Ci-C 6) -haloalkyl, (Ci-Cc) alkylthio, (Ci-C 6) haloalkylthio, hydroxycarbonyl, aryl (Ci-Ce) - alkoxycarbonyl, (C2-Cc>) alkenyloxycarbonyl, aminocarbonyl, (Ci-Ce) - alkylaminocarbonyl, bis [(Ci-C6) alkyl] aminocarbonyl, (C-Ce ) - alkyl [(Ci-C 6) alkyl] aminocarbonyl, (Ci-C6) alkyl [(Ci-C6) - Alkoxyjaminocarbonyl, (C2-Cc>) -Alkenylaminocarbonyl, (C3-C6) - cycloalkylaminocarbonyl, aryl - (C 1 -C 6) -alkylaminocarbonyl, amino, (C 1 -C 6) -alkylamino, (C 1 -C 6 -cycloalkylamino, bis [(C 1 -C 6) -alkyl] -amino, R 24 , R 25 , R 26 , R 28 , R 29 and R 30 are independently hydrogen, (Ci-Ce) - alkyl, fluorine, chlorine, bromine, iodine, (Cs-Cc-cycloalkyl, aryl, heteroaryl, heterocyclyl , (C 2 -C 6) alkenyl, (Ci-C 6) alkoxy, (Ci-C 6) -haloalkyl, (Ci-Ce) - alkylthio, (CrCeJ-haloalkylthio stand,
A9 für O (Sauerstoff), S (Schwefel), N-H, N-CH3, N-OCH3 oder die Gruppierung CHR27 steht und wobei R27 in der Gruppierung CHR27 die Bedeutung gemäß der nachstehenden Definition hat und A 9 is O (oxygen), S (sulfur), NH, N-CH 3 , N-OCH 3 or the moiety CHR 27 and wherein R 27 in the moiety CHR 27 has the meaning as defined below and
R27 für Wasserstoff, Fluor, Chlor, Brom, lod, (Ci-C6)-Alkyl, gegebenenfalls R 27 represents hydrogen, fluorine, chlorine, bromine, iodine, (C 1 -C 6) -alkyl, if appropriate
substituiertes Phenyl, Heteroaryl, Heterocyclyl, (C3-C6)-Cycloalkyl, (C2-C6)-Alkenyl, (Ci-Ce)-Alkoxy, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, (d-C6)- Haloalkoxy, (CrC6)-Haloalkyl, (Ci-C6)-Alkylthio, (Ci-C6)-Haloalkylthio, Hydroxycarbonyl, (Ci-Cr,)-Alkoxycarbonyl, (C3-C6)-Cycloalkoxycarbonyl, Aryl-(Ci-C6)-alkoxycarbonyl, Aminocarbonyl, (d-CeJ-Alkylaminocarbonyl, Bis[(CrC6)-alkyl]aminocarbonyl, (C3-C6)-Cycloalkylaminocarbonyl, Aryl- (Ci-Cö)-alkylaminocarbonyl, Amino, (d-CeJ-Alkylamino, (C3-C6)- Cycloalkylamino, Bis[(Ci-C6)-Alkyl]amino steht. substituted phenyl, heteroaryl, heterocyclyl, (C3-C6) cycloalkyl, (C 2 -C 6) alkenyl, (Ci-Ce) alkoxy, (Ci-C6) alkoxy (Ci-C 6) alkyl (dC 6) - haloalkoxy, (CrC 6) -haloalkyl, (Ci-C 6) alkylthio, (Ci-C 6) haloalkylthio, hydroxycarbonyl, (Ci-Cr,) - alkoxycarbonyl, (C3-C6) - Cycloalkoxycarbonyl, aryl- (Ci-C6) -alkoxycarbonyl, aminocarbonyl, (d-CeJ-alkylaminocarbonyl, bis [(CrC6) -alkyl] aminocarbonyl, (C3-C6) -cycloalkylaminocarbonyl, aryl- (Ci-Cö) -alkylaminocarbonyl, amino , (d-CeJ-alkylamino, (C3-C6) -cycloalkylamino, bis [(Ci-C6) -alkyl] -amino.
Sprühlösung zur Behandlung von Pflanzen, enthaltend eine zur Steigerung der Widerstandsfähigkeit von Pflanzen gegenüber abioti sehen Stressfaktoren wirksame Menge einer oder mehrerer der substituierten l -(Arylethinyl)-, 1 - (Heteroarylethinyl)-, l-(Heterocyclylethinyl)- und 1 -(Cyloalkenylethinyl)- cyclohexanole gemäß einem der Ansprüche 12 oder 13.
A spray solution for the treatment of plants, comprising an effective amount of one or more of the substituted 1- (arylethynyl), 1- (heteroarylethynyl), 1- (heterocyclylethynyl) - and 1- (cycloalkenylethynyl) substituents to enhance plant resistance to abiotic stresses ) - cyclohexanols according to one of claims 12 or 13.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP13798695.6A EP2928296A1 (en) | 2012-12-05 | 2013-12-03 | Use of substituted 1-(aryl ethynyl)-, 1-(heteroaryl ethynyl)-, 1-(heterocyclyl ethynyl)- and 1-(cyloalkenyl ethynyl)-cyclohexanols as active agents against abiotic plant stress |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12195683 | 2012-12-05 | ||
| EP13798695.6A EP2928296A1 (en) | 2012-12-05 | 2013-12-03 | Use of substituted 1-(aryl ethynyl)-, 1-(heteroaryl ethynyl)-, 1-(heterocyclyl ethynyl)- and 1-(cyloalkenyl ethynyl)-cyclohexanols as active agents against abiotic plant stress |
| PCT/EP2013/075324 WO2014086751A1 (en) | 2012-12-05 | 2013-12-03 | Use of substituted 1-(aryl ethynyl)-, 1-(heteroaryl ethynyl)-, 1-(heterocyclyl ethynyl)- and 1-(cyloalkenyl ethynyl)-cyclohexanols as active agents against abiotic plant stress |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP2928296A1 true EP2928296A1 (en) | 2015-10-14 |
Family
ID=47278698
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP13798695.6A Withdrawn EP2928296A1 (en) | 2012-12-05 | 2013-12-03 | Use of substituted 1-(aryl ethynyl)-, 1-(heteroaryl ethynyl)-, 1-(heterocyclyl ethynyl)- and 1-(cyloalkenyl ethynyl)-cyclohexanols as active agents against abiotic plant stress |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20150305334A1 (en) |
| EP (1) | EP2928296A1 (en) |
| JP (1) | JP2016500368A (en) |
| CN (1) | CN105072903A (en) |
| AR (1) | AR093821A1 (en) |
| BR (1) | BR112015012926A2 (en) |
| WO (1) | WO2014086751A1 (en) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102336926B1 (en) | 2014-10-06 | 2021-12-08 | 버텍스 파마슈티칼스 인코포레이티드 | Modulators of cystic fibrosis transmembrane conductance regulator |
| EP3436446B1 (en) | 2016-03-31 | 2023-06-07 | Vertex Pharmaceuticals Incorporated | Modulators of cystic fibrosis transmembrane conductance regulator |
| UA124708C2 (en) | 2016-09-30 | 2021-11-03 | Вертекс Фармасьютікалз Інкорпорейтед | MODULATOR OF THE MUSCULAR FISCOSE REGULATOR OF TRANSMEMBRANE CONDUCTANCE, PHARMACEUTICAL COMPOSITIONS, METHODS OF TREATMENT AND METHOD OF OBTAINING THE MODULATOR |
| AU2017371200B2 (en) | 2016-12-09 | 2021-05-06 | Vertex Pharmaceuticals Incorporated | Modulator of cystic fibrosis transmembrane conductance regulator, pharmaceutical compositions, methods of treatment, and process for making the modulator |
| MA54105A (en) | 2017-06-08 | 2021-09-15 | Vertex Pharma | CYSTIC FIBROSIS TREATMENT METHODS |
| MA49631A (en) | 2017-07-17 | 2020-05-27 | Vertex Pharma | CYSTIC FIBROSIS TREATMENT METHODS |
| KR102606188B1 (en) | 2017-08-02 | 2023-11-23 | 버텍스 파마슈티칼스 인코포레이티드 | Process for producing pyrrolidine compounds |
| US10654829B2 (en) | 2017-10-19 | 2020-05-19 | Vertex Pharmaceuticals Incorporated | Crystalline forms and compositions of CFTR modulators |
| US11465985B2 (en) | 2017-12-08 | 2022-10-11 | Vertex Pharmaceuticals Incorporated | Processes for making modulators of cystic fibrosis transmembrane conductance regulator |
| TWI810243B (en) | 2018-02-05 | 2023-08-01 | 美商維泰克斯製藥公司 | Pharmaceutical compositions for treating cystic fibrosis |
| US11414439B2 (en) | 2018-04-13 | 2022-08-16 | Vertex Pharmaceuticals Incorporated | Modulators of cystic fibrosis transmembrane conductance regulator, pharmaceutical compositions, methods of treatment, and process for making the modulator |
| WO2024153736A1 (en) * | 2023-01-18 | 2024-07-25 | Vib Vzw | Compounds for increasing frost tolerance in plants |
Family Cites Families (233)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1164564A (en) | 1967-08-21 | 1969-09-17 | Shell Int Research | Novel Cyclobexylpentadienone Acid Derivatives, the preparation thereof and Compositions containing the same |
| DE1953152A1 (en) | 1968-10-25 | 1971-01-21 | Fujisawa Pharmaceutical Co | Preparations for regulating the growth of plants |
| DE1905834C3 (en) | 1969-02-06 | 1972-11-09 | Basf Ag | Procedure for avoiding dust and caking of salts or fertilizers |
| DE2906507A1 (en) | 1979-02-20 | 1980-08-28 | Bayer Ag | Plant growth regulating compsn. - contg. alpha amino cyclo:alkanoic acid derivs., e.g. for dwarfing cereals |
| DE2948024A1 (en) | 1979-11-29 | 1981-08-27 | Bayer Ag, 5090 Leverkusen | 1-AMINO-CYCLOPROPANCARBONIC ACID DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS PLANT GROWTH REGULATORS |
| MA19709A1 (en) | 1982-02-17 | 1983-10-01 | Ciba Geigy Ag | APPLICATION OF QUINOLEIN DERIVATIVES TO THE PROTECTION OF CULTIVATED PLANTS. |
| EP0094349B1 (en) | 1982-05-07 | 1994-04-06 | Ciba-Geigy Ag | Use of quinoline derivatives for the protection of cultivated plants |
| DE3335514A1 (en) | 1983-09-30 | 1985-04-18 | Bayer Ag, 5090 Leverkusen | 1-METHYLAMINO-CYCLOPROPAN-1-CARBONIC ACID DERIVATIVES |
| JPS6087254A (en) | 1983-10-19 | 1985-05-16 | Japan Carlit Co Ltd:The | Novel urea compound and herbicide containing the same |
| US4761373A (en) | 1984-03-06 | 1988-08-02 | Molecular Genetics, Inc. | Herbicide resistance in plants |
| US5304732A (en) | 1984-03-06 | 1994-04-19 | Mgi Pharma, Inc. | Herbicide resistance in plants |
| US5331107A (en) | 1984-03-06 | 1994-07-19 | Mgi Pharma, Inc. | Herbicide resistance in plants |
| DE3525205A1 (en) | 1984-09-11 | 1986-03-20 | Hoechst Ag, 6230 Frankfurt | PLANT PROTECTIVE AGENTS BASED ON 1,2,4-TRIAZOLE DERIVATIVES AND NEW DERIVATIVES OF 1,2,4-TRIAZOLE |
| DE3680212D1 (en) | 1985-02-14 | 1991-08-22 | Ciba Geigy Ag | USE OF CHINOLINE DERIVATIVES FOR PROTECTING CROPS. |
| DE3534948A1 (en) | 1985-10-01 | 1987-04-09 | Bayer Ag | FUNGICIDES AND GROWTH REGULATORY AGENTS |
| ATE57390T1 (en) | 1986-03-11 | 1990-10-15 | Plant Genetic Systems Nv | PLANT CELLS OBTAINED BY GENOLOGICAL TECHNOLOGY AND RESISTANT TO GLUTAMINE SYNTHETASE INHIBITORS. |
| US5123951A (en) | 1986-03-31 | 1992-06-23 | Rhone-Poulenc Nederland B.V. | Synergistic plant growth regulator compositions |
| US5276268A (en) | 1986-08-23 | 1994-01-04 | Hoechst Aktiengesellschaft | Phosphinothricin-resistance gene, and its use |
| US5637489A (en) | 1986-08-23 | 1997-06-10 | Hoechst Aktiengesellschaft | Phosphinothricin-resistance gene, and its use |
| US5273894A (en) | 1986-08-23 | 1993-12-28 | Hoechst Aktiengesellschaft | Phosphinothricin-resistance gene, and its use |
| US5605011A (en) | 1986-08-26 | 1997-02-25 | E. I. Du Pont De Nemours And Company | Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase |
| US5378824A (en) | 1986-08-26 | 1995-01-03 | E. I. Du Pont De Nemours And Company | Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase |
| US5013659A (en) | 1987-07-27 | 1991-05-07 | E. I. Du Pont De Nemours And Company | Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase |
| DE3633840A1 (en) | 1986-10-04 | 1988-04-14 | Hoechst Ag | PHENYLPYRAZOLIC CARBONIC ACID DERIVATIVES, THEIR PRODUCTION AND USE AS PLANT GROWTH REGULATORS AND SAFENERS |
| EP0268554B1 (en) | 1986-10-22 | 1991-12-27 | Ciba-Geigy Ag | 1,5-diphenyl pyrazole-3-carbonic-acid derivatives for the protection of cultured plants |
| US5638637A (en) | 1987-12-31 | 1997-06-17 | Pioneer Hi-Bred International, Inc. | Production of improved rapeseed exhibiting an enhanced oleic acid content |
| DE3808896A1 (en) | 1988-03-17 | 1989-09-28 | Hoechst Ag | PLANT PROTECTION AGENTS BASED ON PYRAZOL CARBON SEA DERIVATIVES |
| GB8810120D0 (en) | 1988-04-28 | 1988-06-02 | Plant Genetic Systems Nv | Transgenic nuclear male sterile plants |
| DE3817192A1 (en) | 1988-05-20 | 1989-11-30 | Hoechst Ag | PLANT-PROTECTIVE AGENTS CONTAINING 1,2,4-TRIAZOLE DERIVATIVES AND NEW DERIVATIVES OF 1,2,4-TRIAZOLE |
| US5084082A (en) | 1988-09-22 | 1992-01-28 | E. I. Du Pont De Nemours And Company | Soybean plants with dominant selectable trait for herbicide resistance |
| ES2054088T3 (en) | 1988-10-20 | 1994-08-01 | Ciba Geigy Ag | SULFAMOILFENILUREAS. |
| DD277835A1 (en) | 1988-12-13 | 1990-04-18 | Forschzent Bodenfruchtbarkeit | MEANS FOR INCREASING THE STRESSTOLERANCE OF CULTURAL PLANTS |
| DD277832A1 (en) | 1988-12-13 | 1990-04-18 | Forschzent Bodenfruchtbarkeit | MEANS FOR INCREASING THE STRESSTOLERANCE OF CULTURAL PLANTS |
| US6013861A (en) | 1989-05-26 | 2000-01-11 | Zeneca Limited | Plants and processes for obtaining them |
| CA2039165C (en) | 1989-08-10 | 2005-10-25 | Celestina Mariani | Plants with modified flowers |
| DE3939010A1 (en) | 1989-11-25 | 1991-05-29 | Hoechst Ag | ISOXAZOLINE, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS A PLANT PROTECTIVE AGENT |
| US5908810A (en) | 1990-02-02 | 1999-06-01 | Hoechst Schering Agrevo Gmbh | Method of improving the growth of crop plants which are resistant to glutamine synthetase inhibitors |
| US5739082A (en) | 1990-02-02 | 1998-04-14 | Hoechst Schering Agrevo Gmbh | Method of improving the yield of herbicide-resistant crop plants |
| DE69125991T2 (en) | 1990-04-04 | 1997-09-25 | Pioneer Hi Bred Int | MANUFACTURE OF RAPESEED WITH A REDUCED LEVEL OF SATURATED FATTY ACIDS |
| US5198599A (en) | 1990-06-05 | 1993-03-30 | Idaho Resarch Foundation, Inc. | Sulfonylurea herbicide resistance in plants |
| WO1992000377A1 (en) | 1990-06-25 | 1992-01-09 | Monsanto Company | Glyphosate tolerant plants |
| EP0539588A1 (en) | 1990-07-05 | 1993-05-05 | Nippon Soda Co., Ltd. | Amine derivative |
| FR2667078B1 (en) | 1990-09-21 | 1994-09-16 | Agronomique Inst Nat Rech | DNA SEQUENCE GIVING MALE CYTOPLASMIC STERILITY, MITOCHONDRIAL, MITOCHONDRIA AND PLANT CONTAINING THE SAME, AND PROCESS FOR THE PREPARATION OF HYBRIDS. |
| EP0492366B1 (en) | 1990-12-21 | 1997-03-26 | Hoechst Schering AgrEvo GmbH | New 5-chloroquinolin-8-oxyalkanecarbonic acid derivatives, process for their preparation and their use as antidotes for herbicides |
| DE4103253C2 (en) | 1991-02-04 | 2000-03-23 | Aua Agrar Und Umweltanalytik G | Means to increase the stress tolerance of agricultural and forestry crops |
| DE4104782B4 (en) | 1991-02-13 | 2006-05-11 | Bayer Cropscience Gmbh | Novel plasmids containing DNA sequences that cause changes in carbohydrate concentration and carbohydrate composition in plants, as well as plants and plant cells containing these plasmids |
| US5731180A (en) | 1991-07-31 | 1998-03-24 | American Cyanamid Company | Imidazolinone resistant AHAS mutants |
| DE4128828A1 (en) | 1991-08-30 | 1993-03-04 | Basf Ag | AMMONIUM OR UREA-CONTAINED DISPENSERS AND METHOD FOR THEIR PRODUCTION |
| US6270828B1 (en) | 1993-11-12 | 2001-08-07 | Cargrill Incorporated | Canola variety producing a seed with reduced glucosinolates and linolenic acid yielding an oil with low sulfur, improved sensory characteristics and increased oxidative stability |
| TW259690B (en) | 1992-08-01 | 1995-10-11 | Hoechst Ag | |
| DE4227061A1 (en) | 1992-08-12 | 1994-02-17 | Inst Genbiologische Forschung | A polyfructane sucrase DNA sequence from Erwinia Amylovora |
| GB9218185D0 (en) | 1992-08-26 | 1992-10-14 | Ici Plc | Novel plants and processes for obtaining them |
| DE69233352T2 (en) | 1992-10-14 | 2004-10-07 | Syngenta Ltd | PLANTS AND METHOD FOR THEIR PRODUCTION |
| GB9223454D0 (en) | 1992-11-09 | 1992-12-23 | Ici Plc | Novel plants and processes for obtaining them |
| WO1994015467A1 (en) * | 1993-01-07 | 1994-07-21 | National Research Council Of Canada | Use of compounds to confer low temperature tolerance to plants |
| HU220714B1 (en) | 1993-03-25 | 2002-04-29 | Novartis Ag. | New pesticide proteins and strains |
| EP0928556A3 (en) | 1993-04-27 | 1999-09-15 | Cargill, Incorporated | Non-hydrogenated canola oil for food applications |
| WO1995004826A1 (en) | 1993-08-09 | 1995-02-16 | Institut Für Genbiologische Forschung Berlin Gmbh | Debranching enzymes and dna sequences coding them, suitable for changing the degree of branching of amylopectin starch in plants |
| DE4330960C2 (en) | 1993-09-09 | 2002-06-20 | Aventis Cropscience Gmbh | Combination of DNA sequences that enable the formation of highly amylose-containing starch in plant cells and plants, processes for producing these plants and the modified starch that can be obtained therefrom |
| DE4331448A1 (en) | 1993-09-16 | 1995-03-23 | Hoechst Schering Agrevo Gmbh | Substituted isoxazolines, processes for their preparation, compositions containing them and their use as safeners |
| EP0675198A4 (en) | 1993-10-01 | 1996-01-10 | Mitsubishi Chem Ind | GENE IDENTIFYING A STERILE PLANT CYTOPLASM AND METHOD FOR PREPARING A HYBRID PLANT USING THE SAME. |
| AU692791B2 (en) | 1993-10-12 | 1998-06-18 | Agrigenetics, Inc. | Brassica napus variety AG019 |
| EP0728213B2 (en) | 1993-11-09 | 2008-12-10 | E.I. Du Pont De Nemours And Company | Transgenic fructan accumulating crops and methods for their production |
| CA2186399C (en) | 1994-03-25 | 2001-09-04 | David Cooke | Method for producing altered starch from potato plants |
| DE69535543T2 (en) | 1994-05-18 | 2008-04-30 | Bayer Bioscience Gmbh | FOR ENZYMES WHO HAVE THE ABILITY TO SYNTHESIZE LINEAR ALPHA 1,4-GLUCANE IN PLANTS, MUSHROOMS, AND MICROORGANISMS, ENCODING DNA SEQUENCES |
| CN1156951A (en) | 1994-06-21 | 1997-08-13 | 曾尼卡有限公司 | Novel plants and methods for their preparation |
| US5824790A (en) | 1994-06-21 | 1998-10-20 | Zeneca Limited | Modification of starch synthesis in plants |
| NL1000064C1 (en) | 1994-07-08 | 1996-01-08 | Stichting Scheikundig Onderzoe | Production of oligosaccharides in transgenic plants. |
| DE4441408A1 (en) | 1994-11-10 | 1996-05-15 | Inst Genbiologische Forschung | DNA sequences from Solanum tuberosum encoding enzymes involved in starch synthesis, plasmids, bacteria, plant cells and transgenic plants containing these sequences |
| DE4447387A1 (en) | 1994-12-22 | 1996-06-27 | Inst Genbiologische Forschung | Debranching enzymes from plants and DNA sequences encoding these enzymes |
| WO1996021023A1 (en) | 1995-01-06 | 1996-07-11 | Centrum Voor Plantenveredelings- En Reproduktieonderzoek (Cpro - Dlo) | Dna sequences encoding carbohydrate polymer synthesizing enzymes and method for producing transgenic plants |
| DE19509695A1 (en) | 1995-03-08 | 1996-09-12 | Inst Genbiologische Forschung | Process for the preparation of a modified starch in plants, and the modified starch isolatable from the plants |
| US5853973A (en) | 1995-04-20 | 1998-12-29 | American Cyanamid Company | Structure based designed herbicide resistant products |
| HU226259B1 (en) | 1995-04-20 | 2008-07-28 | American Cyanamid Co | Structure-based designed herbicide resistant products |
| AU706009B2 (en) | 1995-05-05 | 1999-06-03 | Brunob Ii B.V. | Improvements in or relating to plant starch composition |
| FR2734842B1 (en) | 1995-06-02 | 1998-02-27 | Rhone Poulenc Agrochimie | DNA SEQUENCE OF A HYDROXY-PHENYL PYRUVATE DIOXYGENASE GENE AND OBTAINING PLANTS CONTAINING A HYDROXY-PHENYL PYRUVATE DIOXYGENASE GENE, TOLERANT TO CERTAIN HERBICIDES |
| US5712107A (en) | 1995-06-07 | 1998-01-27 | Pioneer Hi-Bred International, Inc. | Substitutes for modified starch and latexes in paper manufacture |
| US6284479B1 (en) | 1995-06-07 | 2001-09-04 | Pioneer Hi-Bred International, Inc. | Substitutes for modified starch and latexes in paper manufacture |
| GB9513881D0 (en) | 1995-07-07 | 1995-09-06 | Zeneca Ltd | Improved plants |
| FR2736926B1 (en) | 1995-07-19 | 1997-08-22 | Rhone Poulenc Agrochimie | 5-ENOL PYRUVYLSHIKIMATE-3-PHOSPHATE SYNTHASE MUTEE, CODING GENE FOR THIS PROTEIN AND PROCESSED PLANTS CONTAINING THIS GENE |
| ES2335494T3 (en) | 1995-09-19 | 2010-03-29 | Bayer Bioscience Gmbh | PROCEDURE FOR THE PRODUCTION OF A MODIFIED ALMIDON. |
| GB9524938D0 (en) | 1995-12-06 | 1996-02-07 | Zeneca Ltd | Modification of starch synthesis in plants |
| DE19601365A1 (en) | 1996-01-16 | 1997-07-17 | Planttec Biotechnologie Gmbh | Nucleic acid molecules from plants encoding enzymes involved in starch synthesis |
| DE19608918A1 (en) | 1996-03-07 | 1997-09-11 | Planttec Biotechnologie Gmbh | Nucleic Acid Molecules Encoding New Debranching Enzymes from Maize |
| US5773704A (en) | 1996-04-29 | 1998-06-30 | Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College | Herbicide resistant rice |
| DE19618125A1 (en) | 1996-05-06 | 1997-11-13 | Planttec Biotechnologie Gmbh | Nucleic acid molecules that encode new potato debranching enzymes |
| DE19619918A1 (en) | 1996-05-17 | 1997-11-20 | Planttec Biotechnologie Gmbh | Nucleic acid molecules encoding soluble starch synthases from maize |
| DE19621522A1 (en) | 1996-05-29 | 1997-12-04 | Hoechst Schering Agrevo Gmbh | New N-acylsulfonamides, new mixtures of herbicides and antidots and their use |
| DE69737448T2 (en) | 1996-05-29 | 2007-11-15 | Bayer Cropscience Ag | NUCLEIC ACID MOLECULES CODING FOR ENZYMES FROM WHEAT INVOLVED IN STARCH SYNTHESIS |
| CA2257622C (en) | 1996-06-12 | 2003-02-11 | Pioneer Hi-Bred International, Inc. | Substitutes for modified starch in paper manufacture |
| WO1997047808A1 (en) | 1996-06-12 | 1997-12-18 | Pioneer Hi-Bred International, Inc. | Substitutes for modified starch in paper manufacture |
| WO1997047806A1 (en) | 1996-06-12 | 1997-12-18 | Pioneer Hi-Bred International, Inc. | Substitutes for modified starch in paper manufacture |
| AUPO069996A0 (en) | 1996-06-27 | 1996-07-18 | Australian National University, The | Manipulation of plant cellulose |
| US5850026A (en) | 1996-07-03 | 1998-12-15 | Cargill, Incorporated | Canola oil having increased oleic acid and decreased linolenic acid content |
| US5773702A (en) | 1996-07-17 | 1998-06-30 | Board Of Trustees Operating Michigan State University | Imidazolinone herbicide resistant sugar beet plants |
| DE19631764A1 (en) | 1996-08-06 | 1998-02-12 | Basf Ag | Use of poly acids to treat mineral fertilisers - where the fertiliser contains nitrification inhibitor in mineral fertiliser, especially new or known pyrazole compound, to reduce volatility |
| EP0929543B1 (en) | 1996-09-26 | 2001-10-31 | Syngenta Participations AG | Herbicidal composition |
| GB9623095D0 (en) | 1996-11-05 | 1997-01-08 | Nat Starch Chem Invest | Improvements in or relating to starch content of plants |
| US6232529B1 (en) | 1996-11-20 | 2001-05-15 | Pioneer Hi-Bred International, Inc. | Methods of producing high-oil seed by modification of starch levels |
| DE19653176A1 (en) | 1996-12-19 | 1998-06-25 | Planttec Biotechnologie Gmbh | New maize nucleic acid molecules and their use to produce a modified starch |
| DE19652961A1 (en) | 1996-12-19 | 1998-06-25 | Hoechst Schering Agrevo Gmbh | New 2-fluoroacrylic acid derivatives, new mixtures of herbicides and antidots and their use |
| CA2193938A1 (en) | 1996-12-24 | 1998-06-24 | David G. Charne | Oilseed brassica containing an improved fertility restorer gene for ogura cytoplasmic male sterility |
| US5981840A (en) | 1997-01-24 | 1999-11-09 | Pioneer Hi-Bred International, Inc. | Methods for agrobacterium-mediated transformation |
| US6071856A (en) | 1997-03-04 | 2000-06-06 | Zeneca Limited | Herbicidal compositions for acetochlor in rice |
| DE19708774A1 (en) | 1997-03-04 | 1998-09-17 | Max Planck Gesellschaft | Enzymes encoding nucleic acid molecules which have fructosyl polymerase activity |
| DE19709775A1 (en) | 1997-03-10 | 1998-09-17 | Planttec Biotechnologie Gmbh | Nucleic acid molecules encoding corn starch phosphorylase |
| DE19727410A1 (en) | 1997-06-27 | 1999-01-07 | Hoechst Schering Agrevo Gmbh | 3- (5-tetrazolylcarbonyl) -2-quinolones and crop protection agents containing them |
| GB9718863D0 (en) | 1997-09-06 | 1997-11-12 | Nat Starch Chem Invest | Improvements in or relating to stability of plant starches |
| DE19742951A1 (en) | 1997-09-29 | 1999-04-15 | Hoechst Schering Agrevo Gmbh | Acylsulfamoylbenzoic acid amides, crop protection agents containing them and process for their preparation |
| DE19749122A1 (en) | 1997-11-06 | 1999-06-10 | Max Planck Gesellschaft | Enzymes encoding nucleic acid molecules that have fructosyl transferase activity |
| FR2770854B1 (en) | 1997-11-07 | 2001-11-30 | Rhone Poulenc Agrochimie | DNA SEQUENCE OF A GENE OF HYDROXY-PHENYL PYRUVATE DIOXYGENASE AND PRODUCTION OF PLANTS CONTAINING SUCH A GENE, HERBICIDE TOLERANT |
| FR2772789B1 (en) | 1997-12-24 | 2000-11-24 | Rhone Poulenc Agrochimie | PROCESS FOR THE ENZYMATIC PREPARATION OF HOMOGENTISATE |
| AU3478499A (en) | 1998-04-09 | 1999-11-01 | E.I. Du Pont De Nemours And Company | Starch r1 phosphorylation protein homologs |
| DE19820607A1 (en) | 1998-05-08 | 1999-11-11 | Hoechst Schering Agrevo Gmbh | New enzyme with starch synthase activity, useful for producing starch for foods and packaging materials |
| DE19820608A1 (en) | 1998-05-08 | 1999-11-11 | Hoechst Schering Agrevo Gmbh | New nucleic acid encoding isoamylase from wheat and related transgenic plants producing starch with altered properties |
| US6891088B1 (en) | 1998-05-13 | 2005-05-10 | Bayer Bioscience Gmbh | Transgenic plants with a modified activity of a plastidial ADP/ATP translocator |
| DE19821614A1 (en) | 1998-05-14 | 1999-11-18 | Hoechst Schering Agrevo Gmbh | Sugar beet mutants which are tolerant to sulfonylurea herbicides |
| EP1092033B1 (en) | 1998-06-15 | 2009-04-15 | Brunob Ii B.V. | Improvements in or relating to plants and plant products |
| US6693185B2 (en) | 1998-07-17 | 2004-02-17 | Bayer Bioscience N.V. | Methods and means to modulate programmed cell death in eukaryotic cells |
| DE19836098A1 (en) | 1998-07-31 | 2000-02-03 | Hoechst Schering Agrevo Gmbh | Plants that synthesize a modified starch, process for producing the plants, their use and the modified starch |
| DE19836099A1 (en) | 1998-07-31 | 2000-02-03 | Hoechst Schering Agrevo Gmbh | Nucleic acid molecules coding for a β-amylase, plants which synthesize a modified starch, process for the preparation of the plants, their use and the modified starch |
| AU6018399A (en) | 1998-08-25 | 2000-03-14 | Pioneer Hi-Bred International, Inc. | Plant glutamine: fructose-6-phosphate amidotransferase nucleic acids |
| HUP0103414A3 (en) | 1998-09-02 | 2005-12-28 | Bayer Bioscience Gmbh | Nucleic acid molecules encoding an amylosucrase |
| DE19924342A1 (en) | 1999-05-27 | 2000-11-30 | Planttec Biotechnologie Gmbh | Genetically modified plant cells and plants with increased activity of an amylosucrase protein and a branching enzyme |
| US6699694B1 (en) | 1998-10-09 | 2004-03-02 | Planttec Biotechnologie Gmbh | Method for producing α-1,6-branched α-1,4-glucans from sucrose |
| US6624139B1 (en) | 1998-11-05 | 2003-09-23 | Eden Bioscience Corporation | Hypersensitive response elicitor-induced stress resistance |
| BR9915152A (en) | 1998-11-09 | 2001-08-07 | Planttec Biotechnologie Gmbh | Rice nucleic acid molecules and their use for the production of modified starch |
| US6531648B1 (en) | 1998-12-17 | 2003-03-11 | Syngenta Participations Ag | Grain processing method and transgenic plants useful therein |
| DE19905069A1 (en) | 1999-02-08 | 2000-08-10 | Planttec Biotechnologie Gmbh | Alternansucrase encoding nucleic acid molecules |
| US6323392B1 (en) | 1999-03-01 | 2001-11-27 | Pioneer Hi-Bred International, Inc. | Formation of brassica napus F1 hybrid seeds which exhibit a highly elevated oleic acid content and a reduced linolenic acid content in the endogenously formed oil of the seeds |
| CN1359422A (en) | 1999-04-29 | 2002-07-17 | 辛甄塔有限公司 | Herbicide resistant plants |
| HUP0201018A2 (en) | 1999-04-29 | 2002-07-29 | Syngenta Ltd | Herbicide resistant plants |
| DE19926771A1 (en) | 1999-06-11 | 2000-12-14 | Aventis Cropscience Gmbh | Nucleic acid molecules from wheat, transgenic plant cells and plants and their use for the production of modified starch |
| DE19937348A1 (en) | 1999-08-11 | 2001-02-22 | Aventis Cropscience Gmbh | Nucleic acid molecules from plants encoding enzymes involved in starch synthesis |
| DE19937643A1 (en) | 1999-08-12 | 2001-02-22 | Aventis Cropscience Gmbh | Transgenic cells and plants with altered activity of the GBSSI and BE proteins |
| AU7647000A (en) | 1999-08-20 | 2001-03-19 | Basf Plant Science Gmbh | Increasing the polysaccharide content in plants |
| US6423886B1 (en) | 1999-09-02 | 2002-07-23 | Pioneer Hi-Bred International, Inc. | Starch synthase polynucleotides and their use in the production of new starches |
| US6472588B1 (en) | 1999-09-10 | 2002-10-29 | Texas Tech University | Transgenic cotton plants with altered fiber characteristics transformed with a sucrose phosphate synthase nucleic acid |
| GB9921830D0 (en) | 1999-09-15 | 1999-11-17 | Nat Starch Chem Invest | Plants having reduced activity in two or more starch-modifying enzymes |
| AR025996A1 (en) | 1999-10-07 | 2002-12-26 | Valigen Us Inc | NON-TRANSGENIC PLANTS RESISTANT TO HERBICIDES. |
| EP1261252B1 (en) | 2000-03-09 | 2013-04-24 | E.I. Du Pont De Nemours And Company | Sulfonylurea-tolerant sunflower plants |
| BR0109118A (en) | 2000-03-09 | 2002-11-26 | Monsanto Technology Llc | Methods for producing glyphosate tolerant plants and compositions thereof |
| AU8786201A (en) | 2000-09-29 | 2002-04-08 | Syngenta Ltd | Herbicide resistant plants |
| US6734340B2 (en) | 2000-10-23 | 2004-05-11 | Bayer Cropscience Gmbh | Monocotyledon plant cells and plants which synthesise modified starch |
| AR031027A1 (en) | 2000-10-23 | 2003-09-03 | Syngenta Participations Ag | AGROCHEMICAL COMPOSITIONS |
| EP1399566A2 (en) | 2000-10-30 | 2004-03-24 | Maxygen, Inc. | Novel glyphosate n-acetyltransferase (gat) genes |
| FR2815969B1 (en) | 2000-10-30 | 2004-12-10 | Aventis Cropscience Sa | TOLERANT PLANTS WITH HERBICIDES BY METABOLIC BYPASS |
| BR0115782A (en) | 2000-12-08 | 2004-01-20 | Commonwealh Scient And Ind Res | Modification of sucrose synthase gene expression in plant tissue and uses |
| US20040107461A1 (en) | 2001-03-30 | 2004-06-03 | Padma Commuri | Glucan chain length domains |
| ATE394497T1 (en) | 2001-06-12 | 2008-05-15 | Bayer Cropscience Ag | TRANSGENIC PLANTS THAT PRODUCE STARCH WITH HIGH AMYLOSE CONTENT |
| US20030084473A1 (en) | 2001-08-09 | 2003-05-01 | Valigen | Non-transgenic herbicide resistant plants |
| US7169982B2 (en) | 2001-10-17 | 2007-01-30 | Basf Plant Science Gmbh | Starch |
| DE10208132A1 (en) | 2002-02-26 | 2003-09-11 | Planttec Biotechnologie Gmbh | Process for the production of maize plants with an increased leaf starch content and their use for the production of maize silage |
| WO2003092360A2 (en) | 2002-04-30 | 2003-11-13 | Verdia, Inc. | Novel glyphosate-n-acetyltransferase (gat) genes |
| GB0213715D0 (en) | 2002-06-14 | 2002-07-24 | Syngenta Ltd | Chemical compounds |
| FR2844142B1 (en) | 2002-09-11 | 2007-08-17 | Bayer Cropscience Sa | TRANSFORMED PLANTS WITH ENHANCED PRENYLQUINON BIOSYNTHESIS |
| PL377055A1 (en) | 2002-10-29 | 2006-01-23 | Basf Plant Science Gmbh | Compositions and methods for identifying plants having increased tolerance to imidazolinone herbicides |
| US20040110443A1 (en) | 2002-12-05 | 2004-06-10 | Pelham Matthew C. | Abrasive webs and methods of making the same |
| DK1578973T3 (en) | 2002-12-19 | 2008-11-24 | Bayer Cropscience Ag | Plant cells and plants that synthesize a starch with increased final viscosity |
| RU2005130914A (en) | 2003-03-07 | 2006-06-10 | БАСФ ПЛАНТ САЙЕНС ГмбХ (DE) | IMPROVED PRODUCTION OF AMYLOSIS IN PLANTS |
| MXPA05010296A (en) | 2003-03-26 | 2005-11-17 | Bayer Cropscience Gmbh | Use of aromatic hydroxy compounds as safeners. |
| JP4960699B2 (en) | 2003-04-09 | 2012-06-27 | バイエル・バイオサイエンス・エヌ・ヴェー | Methods and means for increasing plant tolerance to stress conditions |
| EP2535414B1 (en) | 2003-04-29 | 2017-12-13 | Pioneer Hi-Bred International Inc. | Novel glyphosate-n-acetyltransferase (gat) genes |
| TWI312272B (en) | 2003-05-12 | 2009-07-21 | Sumitomo Chemical Co | Pyrimidine compound and pests controlling composition containing the same |
| BRPI0410544A (en) | 2003-05-22 | 2006-06-20 | Syngenta Participations Ag | modified starch uses, processes for the production of the same |
| MXPA05012733A (en) | 2003-05-28 | 2006-05-17 | Basf Ag | Wheat plants having increased tolerance to imidazolinone herbicides. |
| EP1493328A1 (en) | 2003-07-04 | 2005-01-05 | Institut National De La Recherche Agronomique | Method of producing double low restorer lines of brassica napus having a good agronomic value |
| US7547819B2 (en) | 2003-07-31 | 2009-06-16 | Toyo Boseki Kabushiki Kaisha | Plant producing hyaluronic acid |
| DE10335725A1 (en) | 2003-08-05 | 2005-03-03 | Bayer Cropscience Gmbh | Safener based on aromatic-aliphatic carboxylic acid derivatives |
| DE10335726A1 (en) | 2003-08-05 | 2005-03-03 | Bayer Cropscience Gmbh | Use of hydroxyaromatics as safener |
| WO2005017157A1 (en) | 2003-08-15 | 2005-02-24 | Commonwealth Scientific And Industrial Research Organisation (Csiro) | Methods and means for altering fiber characteristics in fiber-producing plants |
| ES2743420T3 (en) | 2003-08-29 | 2020-02-19 | Instituto Nac De Tecnologia Agropecuaria | Rice plants that have increased tolerance against imidazolinone herbicides |
| WO2005030941A1 (en) | 2003-09-30 | 2005-04-07 | Bayer Cropscience Gmbh | Plants with increased activity of a class 3 branching enzyme |
| DE602004030613D1 (en) | 2003-09-30 | 2011-01-27 | Bayer Cropscience Ag | PLANTS WITH REDUCED ACTIVITY OF A CLASS 3 BRANCHING SYSTEM |
| UA79404C2 (en) | 2003-10-02 | 2007-06-11 | Basf Ag | 2-cyanobenzenesulfonamide for controlling pests |
| GB0329744D0 (en) | 2003-12-23 | 2004-01-28 | Koninkl Philips Electronics Nv | A beverage maker incorporating multiple beverage collection chambers |
| SI1717237T1 (en) | 2004-02-18 | 2011-03-31 | Ishihara Sangyo Kaisha | Anthranilamides, process for the production thereof, and pest controllers containing the same |
| CN102558082B (en) | 2004-03-05 | 2015-09-30 | 日产化学工业株式会社 | Isoxazoline-substituted benzamide compound prepare intermediate |
| CA2557843C (en) | 2004-03-05 | 2015-06-02 | Bayer Cropscience Gmbh | Plants with reduced activity of a starch phosphorylating enzyme |
| AR048024A1 (en) | 2004-03-05 | 2006-03-22 | Bayer Cropscience Gmbh | PLANTS WITH INCREASED ACTIVITY OF DIFFERENT ENZYMES FOSFORILANTES DEL ALMIDON |
| AR048025A1 (en) | 2004-03-05 | 2006-03-22 | Bayer Cropscience Gmbh | PLANTS WITH INCREASED ACTIVITY OF AN ALMIDON FOSFORILING ENZYME |
| AR048026A1 (en) | 2004-03-05 | 2006-03-22 | Bayer Cropscience Gmbh | PROCEDURES FOR THE IDENTIFICATION OF PROTEINS WITH ENZYMATIC ACTIVITY FOSFORILADORA DE ALMIDON |
| US7432082B2 (en) | 2004-03-22 | 2008-10-07 | Basf Ag | Methods and compositions for analyzing AHASL genes |
| DE102004023332A1 (en) | 2004-05-12 | 2006-01-19 | Bayer Cropscience Gmbh | Quinoxaline-2-one derivatives, crop protection agents containing them, and processes for their preparation and their use |
| AU2005262525A1 (en) | 2004-06-16 | 2006-01-19 | Basf Plant Science Gmbh | Polynucleotides encoding mature AHASL proteins for creating imidazolinone-tolerant plants |
| DE102004029763A1 (en) | 2004-06-21 | 2006-01-05 | Bayer Cropscience Gmbh | Plants that produce amylopectin starch with new properties |
| BRPI0513981A (en) | 2004-07-30 | 2008-05-20 | Basf Agrochemical Products Bv | plant, seed, methods for controlling weeds in the vicinity of a sunflower plant and a transformed plant, for increasing ahas activity in a plant, for producing a herbicide resistant plant, for enhancing herbicide tolerance in a tolerant plant the herbicide, to select a transformed plant cell, to increase the herbicide resistance of a plant, and to combat undesirable vegetation, isolated polynucleotide molecule, expression cassette, non-human host cell, transformation vector, plant cell transformed and isolated polypeptide |
| US20070250946A1 (en) | 2004-08-04 | 2007-10-25 | Robert Ascenzi | Monocot Ahass Sequences and Methods of Use |
| PT1786908E (en) | 2004-08-18 | 2010-04-29 | Bayer Cropscience Ag | Plants with increased plastidic activity of r3 starch-phosphorylating enzyme |
| WO2006021972A1 (en) | 2004-08-26 | 2006-03-02 | Dhara Vegetable Oil And Foods Company Limited | A novel cytoplasmic male sterility system for brassica species and its use for hybrid seed production in indian oilseed mustard brassica juncea |
| DE102004044262A1 (en) | 2004-09-10 | 2006-03-16 | Basf Ag | Process for the catalytic reduction of alkyne compounds |
| CA2579592C (en) | 2004-09-23 | 2018-01-02 | Bayer Cropscience Gmbh | Plant cells that comprise a nucleic acid encoding hyaluronan synthase, and methods and means for producing hyaluronan |
| CA2581725C (en) | 2004-10-20 | 2013-01-08 | Kumiai Chemical Industry Co., Ltd. | 3-triazolylphenyl sulfide derivative, and insecticide, miticide and nematicide containing it as an active ingredient |
| JP2008521762A (en) | 2004-11-26 | 2008-06-26 | ビーエーエスエフ ソシエタス・ヨーロピア | Novel 2-cyano-3- (halo) alkoxy-benzenesulfonamide compounds for controlling animal pests |
| AR051690A1 (en) | 2004-12-01 | 2007-01-31 | Basf Agrochemical Products Bv | MUTATION INVOLVED IN THE INCREASE OF TOLERANCE TO IMIDAZOLINONE HERBICIDES IN PLANTS |
| EP1672075A1 (en) | 2004-12-17 | 2006-06-21 | Bayer CropScience GmbH | Transformed plant expressing a dextransucrase and synthesizing a modified starch |
| EP1679374A1 (en) | 2005-01-10 | 2006-07-12 | Bayer CropScience GmbH | Transformed plant expressing a mutansucrase and synthesizing a modified starch |
| AR053834A1 (en) | 2005-03-24 | 2007-05-23 | Basf Ag | COMPOUNDS OF 2-CYANOBENCENOSULFONAMIDE FOR THE TREATMENT OF SEEDS |
| JP2006304779A (en) | 2005-03-30 | 2006-11-09 | Toyobo Co Ltd | Hexosamine high production plant |
| EP1707632A1 (en) | 2005-04-01 | 2006-10-04 | Bayer CropScience GmbH | Phosphorylated waxy potato starch |
| EP1710315A1 (en) | 2005-04-08 | 2006-10-11 | Bayer CropScience GmbH | High phosphate starch |
| TWI388282B (en) | 2005-06-01 | 2013-03-11 | Meiji Seika Pharma Co Ltd | Pest control agents |
| EP1893759B1 (en) | 2005-06-15 | 2009-08-12 | Bayer BioScience N.V. | Methods for increasing the resistance of plants to hypoxic conditions |
| MX2008000097A (en) | 2005-06-24 | 2008-03-19 | Bayer Bioscience Nv | Methods for altering the reactivity of plant cell walls. |
| AR054174A1 (en) | 2005-07-22 | 2007-06-06 | Bayer Cropscience Gmbh | OVERPRINTING OF ALMIDON SYNTHEASE IN VEGETABLES |
| JPWO2007023719A1 (en) | 2005-08-22 | 2009-02-26 | クミアイ化学工業株式会社 | Pesticide mitigation agent and herbicide composition with reduced phytotoxicity |
| ATE544861T1 (en) | 2005-08-24 | 2012-02-15 | Pioneer Hi Bred Int | METHODS AND COMPOSITIONS FOR EXPRESSING A POLYNUCLEOTIDE OF INTEREST |
| WO2007023764A1 (en) | 2005-08-26 | 2007-03-01 | Kumiai Chemical Industry Co., Ltd. | Agent for reduction of harmful effect of herbicide and herbicide composition having reduced harmful effect |
| CA2617803C (en) | 2005-08-31 | 2012-05-29 | Monsanto Technology Llc | Nucleotide sequences encoding insecticidal proteins |
| CA2624973C (en) | 2005-10-05 | 2016-01-19 | Bayer Cropscience Ag | Production of hyaluronan from plants transgenic for hyaluronan synthase, gfat and udp-glucose dehydrogenase |
| US10428341B2 (en) | 2005-10-05 | 2019-10-01 | Basf Se | Transgenic potato plants with increased hyaluronan production |
| US20080250533A1 (en) | 2005-10-05 | 2008-10-09 | Claus Frohberg | Plants With an Increased Production of Hyaluronan II |
| DK1937664T3 (en) | 2005-10-14 | 2011-07-18 | Sumitomo Chemical Co | Hydrazide compound and pesticide use of the same |
| WO2007057407A2 (en) | 2005-11-21 | 2007-05-24 | Basf Se | Insecticidal methods using 3-amino-1,2-benzisothiazole derivatives |
| TW200803740A (en) | 2005-12-16 | 2008-01-16 | Du Pont | 5-aryl isoxazolines for controlling invertebrate pests |
| DE102006015470A1 (en) | 2006-03-31 | 2007-10-04 | Bayer Cropscience Ag | New cyclic enamine ketone derivatives useful for controlling pests, especially insects |
| DE102006015467A1 (en) | 2006-03-31 | 2007-10-04 | Bayer Cropscience Ag | New cyclic enamine ketone derivatives useful for controlling pests, especially insects |
| DE102006015468A1 (en) | 2006-03-31 | 2007-10-04 | Bayer Cropscience Ag | New cyclic enamine ketone derivatives useful for controlling pests, especially insects |
| TWI381811B (en) | 2006-06-23 | 2013-01-11 | Dow Agrosciences Llc | A method to control insects resistant to common insecticides |
| JP5047588B2 (en) | 2006-10-31 | 2012-10-10 | Meiji Seikaファルマ株式会社 | Quinoline derivatives and agricultural and horticultural insecticides comprising the same |
| EA200901143A1 (en) | 2007-03-01 | 2010-04-30 | Басф Се | PESTICIDAL ACTIVE MIXTURES INCLUDING AMINOTHASOLINE CONNECTIONS |
| EP1987718A1 (en) | 2007-04-30 | 2008-11-05 | Bayer CropScience AG | Utilisation of pyridine-2-oxy-3-carbon amides as safener |
| EP1987717A1 (en) | 2007-04-30 | 2008-11-05 | Bayer CropScience AG | Pyridon carboxamides, agents containing these but not impacting useful plants and method for their manufacture and application |
| CN101784188B (en) | 2007-06-29 | 2014-02-12 | 奥克塞拉有限公司 | Alkynylphenyl derivatives for use in the treatment of ophthalmic diseases and disorders |
| GB0720126D0 (en) | 2007-10-15 | 2007-11-28 | Syngenta Participations Ag | Chemical compounds |
| EP2111223A4 (en) | 2007-11-01 | 2012-08-15 | Acucela Inc | AMIN DERIVATIVE COMPOUNDS FOR THE TREATMENT OF EYE DISEASES AND DRESSES |
| JP5268461B2 (en) | 2008-07-14 | 2013-08-21 | Meiji Seikaファルマ株式会社 | PF1364 substance, its production method, production strain, and agricultural and horticultural insecticide containing the same as an active ingredient |
| FR2934943B1 (en) | 2008-08-12 | 2011-06-17 | Algieplus | USE OF APIOGALACTURONANES AND ITS DERIVATIVES FOR THE STIMULATION OF DEFENSE AND RESISTANCE REACTIONS OF PLANTS AGAINST BIOTIC AND ABIOTIC STRESS |
| CA2647900C (en) | 2008-12-23 | 2017-05-16 | National Research Council Of Canada | Inhibitors of a 9-cis-epoxycarotenoid dioxygenase |
| WO2010122956A1 (en) | 2009-04-20 | 2010-10-28 | 花王株式会社 | Composition for imparting stress tolerance to plant |
| EP2248421A1 (en) | 2009-05-07 | 2010-11-10 | GMI - Gregor-Mendel-Institut für Molekulare Pflanzenbiologie GmbH | Accumulation of biomass in plants |
| AR090010A1 (en) * | 2011-04-15 | 2014-10-15 | Bayer Cropscience Ag | 5- (CICLOHEX-2-EN-1-IL) -PENTA-2,4-DIENOS AND 5- (CICLOHEX-2-EN-1-IL) -PENT-2-EN-4-INOS REPLACED AS ACTIVE PRINCIPLES AGAINST THE ABIOTIC STRESS OF PLANTS, USES AND TREATMENT METHODS |
| AR085585A1 (en) * | 2011-04-15 | 2013-10-09 | Bayer Cropscience Ag | VINIL- AND ALQUINILCICLOHEXANOLES SUBSTITUTED AS ACTIVE PRINCIPLES AGAINST STRIPS ABIOTIQUE OF PLANTS |
-
2013
- 2013-12-03 EP EP13798695.6A patent/EP2928296A1/en not_active Withdrawn
- 2013-12-03 BR BR112015012926A patent/BR112015012926A2/en not_active IP Right Cessation
- 2013-12-03 WO PCT/EP2013/075324 patent/WO2014086751A1/en not_active Ceased
- 2013-12-03 JP JP2015545777A patent/JP2016500368A/en active Pending
- 2013-12-03 CN CN201380072080.5A patent/CN105072903A/en active Pending
- 2013-12-03 US US14/647,852 patent/US20150305334A1/en not_active Abandoned
- 2013-12-05 AR ARP130104522A patent/AR093821A1/en unknown
Non-Patent Citations (1)
| Title |
|---|
| See references of WO2014086751A1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| BR112015012926A2 (en) | 2017-07-11 |
| WO2014086751A1 (en) | 2014-06-12 |
| CN105072903A (en) | 2015-11-18 |
| JP2016500368A (en) | 2016-01-12 |
| AR093821A1 (en) | 2015-06-24 |
| US20150305334A1 (en) | 2015-10-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP2611300B1 (en) | Substituted annelated dihydropyrimidinone compounds | |
| EP2658376A1 (en) | Use of substituted spirocyclic sulfonamidocarboxylic acids, carboxylic esters thereof, carboxamides thereof and carbonitriles thereof or salts thereof for enhancement of stress tolerance in plants | |
| EP2892345A1 (en) | Use of substituted 2-amidobenzimidazoles, 2-amidobenzoxazoles and 2-amidobenzothiazoles or salts thereof as active substances against abiotic plant stress | |
| AU2012242124B2 (en) | Substituted 5-(cyclohex-2-en-1-yl)-penta-2,4-dienes and 5-(cyclohex-2-en-1-yl)-pent-2-en-4-ynes as active agents against abiotic stress in plants | |
| EP2729007A1 (en) | Use of substituted isoquinolinones, isoquinolindiones, isoquinolintriones and dihydroisoquinolinones or in each case salts thereof as active agents against abiotic stress in plants | |
| EP2697214A1 (en) | Substituted vinyl and alkinyl cyclohexenols as active agents against abiotic stress in plants | |
| EP2928296A1 (en) | Use of substituted 1-(aryl ethynyl)-, 1-(heteroaryl ethynyl)-, 1-(heterocyclyl ethynyl)- and 1-(cyloalkenyl ethynyl)-cyclohexanols as active agents against abiotic plant stress | |
| EP2547204A2 (en) | Aryl and hetaryl sulfonamides as active agents against abiotic plant stress | |
| EP2928297A1 (en) | Use of substituted 1-(aryl ethynyl)-, 1-(heteroaryl ethynyl)-, 1-(heterocyclyl ethynyl)- and 1-(cyloalkenyl ethynyl)-bicycloalkanols as active agents against abiotic plant stress | |
| EP2757886A1 (en) | Use of 4-substituted 1-phenyl-pyrazole-3-carboxylic-acid derivatives as agents against abiotic plant stress | |
| EP2892344A1 (en) | Use of substituted benzodiazepinones and benzazepinones or the salts thereof as active substances against abiotic plant stress | |
| EP2542533A1 (en) | Fluoroalkyl-substituted 2-amidobenzimidazoles and the use thereof for boosting stress tolerance in plants | |
| EP2510786A1 (en) | Substituted Prop-2-in-1-ol and Prop-2-en-1-ol derivatives | |
| JP2014515746A (en) | Substituted 5- (bicyclo [4.1.0] hept-3-en-2-yl) penta-2,4-dienes as active compounds against abiotic plant stress and 5- (bicyclo [4.1. 0] hept-3-en-2-yl) pent-2-en-4-ynes | |
| EP2740356A1 (en) | Substituted (2Z)-5(1-Hydroxycyclohexyl)pent-2-en-4-inic acid derivatives | |
| EP2892343A1 (en) | Use of substituted 2,3-dihydro-1-benzofuran-4-carboxylic acids or salts thereof as active substances against abiotic plant stress | |
| EP2740720A1 (en) | Substituted bicyclic and tricyclic pent-2-en-4-inic acid derivatives and their use for enhancing the stress tolerance in plants | |
| EP2555626A2 (en) | Use of derivatives of the (1-cyanocyclopropyl)phenylphosphinic acid, the esters thereof and/or the salts thereof for enhancing the tolerance of plants to abiotic stress |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
| 17P | Request for examination filed |
Effective date: 20150706 |
|
| AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR |
|
| AX | Request for extension of the european patent |
Extension state: BA ME |
|
| DAX | Request for extension of the european patent (deleted) | ||
| STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN |
|
| 18D | Application deemed to be withdrawn |
Effective date: 20160216 |