SK82694A3 - Pyrimidinylacryle acid derivatives, method of their preparation and fungicidal compositions containt these derivatives - Google Patents

Pyrimidinylacryle acid derivatives, method of their preparation and fungicidal compositions containt these derivatives Download PDF

Info

Publication number: SK82694A3
Authority: SK; Slovakia
Prior art keywords: group; carbon atoms; methyl; alkyl; phenyl
Prior art date: 1993-07-12

Application number

SK826-94A

Other languages

English (en)

Slovak (sk)

Inventor

Martin Eberle

Fritz Schaub

Gerald Wayne Craig

Original Assignee

Sandoz Ag

Priority date (The priority date 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 date listed.)

1993-07-12

Filing date

1994-07-11

Publication date

1995-03-08

1994-07-11 Application filed by Sandoz Ag filed Critical Sandoz Ag

1995-03-08 Publication of SK82694A3 publication Critical patent/SK82694A3/sk

Links

239000000203 mixture Substances 0.000 title claims abstract description 26
238000002360 preparation method Methods 0.000 title claims abstract description 7
238000000034 method Methods 0.000 title claims description 13
230000000855 fungicidal effect Effects 0.000 title claims description 8
239000002253 acid Substances 0.000 title description 3
-1 C1-10haloalkyl Chemical group 0.000 claims abstract description 353
150000001875 compounds Chemical class 0.000 claims abstract description 93
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 43
125000003118 aryl group Chemical group 0.000 claims abstract description 26
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 11
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 11
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 10
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
239000001257 hydrogen Substances 0.000 claims abstract description 7
125000005418 aryl aryl group Chemical group 0.000 claims abstract description 4
125000005325 aryloxy aryl group Chemical group 0.000 claims abstract description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 75
125000000217 alkyl group Chemical group 0.000 claims description 48
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
125000001424 substituent group Chemical group 0.000 claims description 15
125000003545 alkoxy group Chemical group 0.000 claims description 13
229910052736 halogen Inorganic materials 0.000 claims description 12
150000002367 halogens Chemical group 0.000 claims description 12
125000004093 cyano group Chemical group *C#N 0.000 claims description 10
125000004104 aryloxy group Chemical group 0.000 claims description 9
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
125000002102 aryl alkyloxo group Chemical group 0.000 claims description 8
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
229910052799 carbon Inorganic materials 0.000 claims description 8
239000003085 diluting agent Substances 0.000 claims description 8
125000001188 haloalkyl group Chemical group 0.000 claims description 8
125000001544 thienyl group Chemical group 0.000 claims description 8
125000004438 haloalkoxy group Chemical group 0.000 claims description 7
125000005843 halogen group Chemical group 0.000 claims description 7
241000233866 Fungi Species 0.000 claims description 6
238000007069 methylation reaction Methods 0.000 claims description 5
125000004414 alkyl thio group Chemical group 0.000 claims description 4
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
150000003254 radicals Chemical class 0.000 claims description 4
VFUQDUGKYYDRMT-UHFFFAOYSA-N 3-methoxyprop-2-enoic acid Chemical compound COC=CC(O)=O VFUQDUGKYYDRMT-UHFFFAOYSA-N 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
125000005037 alkyl phenyl group Chemical group 0.000 claims description 3
125000005127 aryl alkoxy alkyl group Chemical group 0.000 claims description 3
125000003710 aryl alkyl group Chemical group 0.000 claims description 3
150000005840 aryl radicals Chemical group 0.000 claims description 3
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 3
125000002541 furyl group Chemical group 0.000 claims description 3
125000005059 halophenyl group Chemical group 0.000 claims description 3
125000004446 heteroarylalkyl group Chemical group 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims description 3
230000003032 phytopathogenic effect Effects 0.000 claims description 3
125000004076 pyridyl group Chemical group 0.000 claims description 3
125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 2
125000004663 dialkyl amino group Chemical group 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
125000001624 naphthyl group Chemical group 0.000 claims description 2
125000005359 phenoxyalkyl group Chemical group 0.000 claims description 2
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims 1
125000006267 biphenyl group Chemical group 0.000 claims 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract description 2
125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract 1
125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 17
241000196324 Embryophyta Species 0.000 description 17
238000006243 chemical reaction Methods 0.000 description 17
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
239000000725 suspension Substances 0.000 description 15
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
239000004480 active ingredient Substances 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
241000209140 Triticum Species 0.000 description 10
235000021307 Triticum Nutrition 0.000 description 10
238000001035 drying Methods 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000002585 base Substances 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 9
229910000027 potassium carbonate Inorganic materials 0.000 description 9
235000011181 potassium carbonates Nutrition 0.000 description 9
239000000047 product Substances 0.000 description 9
239000000243 solution Substances 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 8
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
239000002904 solvent Substances 0.000 description 8
239000007921 spray Substances 0.000 description 8
240000005979 Hordeum vulgare Species 0.000 description 7
235000007340 Hordeum vulgare Nutrition 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
238000010992 reflux Methods 0.000 description 7
238000003756 stirring Methods 0.000 description 7
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 6
125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
238000001704 evaporation Methods 0.000 description 6
230000008020 evaporation Effects 0.000 description 6
238000001914 filtration Methods 0.000 description 6
238000009472 formulation Methods 0.000 description 6
230000002538 fungal effect Effects 0.000 description 6
239000012442 inert solvent Substances 0.000 description 6
TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 6
244000052769 pathogen Species 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 description 5
241000220225 Malus Species 0.000 description 5
235000021016 apples Nutrition 0.000 description 5
238000009835 boiling Methods 0.000 description 5
239000012267 brine Substances 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 5
238000000605 extraction Methods 0.000 description 5
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
239000002689 soil Substances 0.000 description 5
239000007787 solid Substances 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
240000008067 Cucumis sativus Species 0.000 description 4
206010061217 Infestation Diseases 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
244000046052 Phaseolus vulgaris Species 0.000 description 4
241000228454 Pyrenophora graminea Species 0.000 description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
239000013543 active substance Substances 0.000 description 4
125000002947 alkylene group Chemical group 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
125000001309 chloro group Chemical group Cl* 0.000 description 4
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 4
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 4
239000008187 granular material Substances 0.000 description 4
238000005984 hydrogenation reaction Methods 0.000 description 4
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
125000004430 oxygen atom Chemical group O* 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
239000012312 sodium hydride Substances 0.000 description 4
239000004094 surface-active agent Substances 0.000 description 4
VOOQEOLOKRTHEB-UHFFFAOYSA-N 2-(2,6-dimethyl-4-oxo-1h-pyrimidin-5-yl)acetic acid Chemical compound CC1=NC(=O)C(CC(O)=O)=C(C)N1 VOOQEOLOKRTHEB-UHFFFAOYSA-N 0.000 description 3
HSXWQMNKBWSOSA-UHFFFAOYSA-N 2-(6-methyl-4-oxo-2-sulfanylidene-1h-pyrimidin-5-yl)acetic acid Chemical compound CC=1NC(=S)NC(=O)C=1CC(O)=O HSXWQMNKBWSOSA-UHFFFAOYSA-N 0.000 description 3
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
125000006495 3-trifluoromethyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])*)C(F)(F)F 0.000 description 3
241000228456 Leptosphaeria Species 0.000 description 3
235000007688 Lycopersicon esculentum Nutrition 0.000 description 3
235000010627 Phaseolus vulgaris Nutrition 0.000 description 3
241000317981 Podosphaera fuliginea Species 0.000 description 3
241000221300 Puccinia Species 0.000 description 3
241000228453 Pyrenophora Species 0.000 description 3
240000003768 Solanum lycopersicum Species 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
241000221577 Uromyces appendiculatus Species 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
125000004429 atom Chemical group 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
235000013339 cereals Nutrition 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
125000000753 cycloalkyl group Chemical group 0.000 description 3
238000004821 distillation Methods 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
125000001153 fluoro group Chemical group F* 0.000 description 3
239000000417 fungicide Substances 0.000 description 3
ZOODCLCPJFMQLY-UHFFFAOYSA-N methyl 2-(6-methyl-2-methylsulfanyl-4-oxo-1h-pyrimidin-5-yl)acetate Chemical compound COC(=O)CC1=C(C)N=C(SC)N=C1O ZOODCLCPJFMQLY-UHFFFAOYSA-N 0.000 description 3
AUYFEPSQLZTFBK-UHFFFAOYSA-N methyl 2-(6-methyl-4-oxo-1h-pyrimidin-5-yl)acetate Chemical compound COC(=O)CC1=C(C)N=CN=C1O AUYFEPSQLZTFBK-UHFFFAOYSA-N 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000002245 particle Substances 0.000 description 3
230000000704 physical effect Effects 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000000454 talc Substances 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
238000005160 1H NMR spectroscopy Methods 0.000 description 2
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 2
125000006184 2,5-dimethyl benzyl group Chemical group [H]C1=C(C([H])=C(C(=C1[H])C([H])([H])[H])C([H])([H])*)C([H])([H])[H] 0.000 description 2
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
FQLNIJUFWMYMST-UHFFFAOYSA-N 2-pyrimidin-2-ylprop-2-enoic acid Chemical class OC(=O)C(=C)C1=NC=CC=N1 FQLNIJUFWMYMST-UHFFFAOYSA-N 0.000 description 2
239000005995 Aluminium silicate Substances 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
241001480061 Blumeria graminis Species 0.000 description 2
238000003512 Claisen condensation reaction Methods 0.000 description 2
235000009849 Cucumis sativus Nutrition 0.000 description 2
235000010799 Cucumis sativus var sativus Nutrition 0.000 description 2
241000221785 Erysiphales Species 0.000 description 2
241000510928 Erysiphe necator Species 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
239000005909 Kieselgur Substances 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
241000736122 Parastagonospora nodorum Species 0.000 description 2
241001281803 Plasmopara viticola Species 0.000 description 2
241001337928 Podosphaera leucotricha Species 0.000 description 2
239000007868 Raney catalyst Substances 0.000 description 2
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
229910000564 Raney nickel Inorganic materials 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
241000228452 Venturia inaequalis Species 0.000 description 2
229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
150000008041 alkali metal carbonates Chemical class 0.000 description 2
229910000102 alkali metal hydride Inorganic materials 0.000 description 2
150000008046 alkali metal hydrides Chemical class 0.000 description 2
FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
235000012211 aluminium silicate Nutrition 0.000 description 2
239000004305 biphenyl Substances 0.000 description 2
235000010290 biphenyl Nutrition 0.000 description 2
UBXYXCRCOKCZIT-UHFFFAOYSA-N biphenyl-3-ol Chemical group OC1=CC=CC(C=2C=CC=CC=2)=C1 UBXYXCRCOKCZIT-UHFFFAOYSA-N 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 2
239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
239000012320 chlorinating reagent Substances 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 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
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 2
235000013399 edible fruits Nutrition 0.000 description 2
230000000694 effects Effects 0.000 description 2
150000002191 fatty alcohols Chemical class 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
125000005553 heteroaryloxy group Chemical group 0.000 description 2
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
LVLJUGZMVXFFKV-UHFFFAOYSA-N methyl 2-(6-methyl-4-oxo-2-sulfanylidene-1h-pyrimidin-5-yl)acetate Chemical compound COC(=O)CC1=C(C)N=C(S)N=C1O LVLJUGZMVXFFKV-UHFFFAOYSA-N 0.000 description 2
230000001035 methylating effect Effects 0.000 description 2
238000002156 mixing Methods 0.000 description 2
125000000896 monocarboxylic acid group Chemical group 0.000 description 2
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 2
RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 2
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
239000000843 powder Substances 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
230000035939 shock Effects 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
239000011593 sulfur Substances 0.000 description 2
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 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
235000013311 vegetables Nutrition 0.000 description 2
239000004563 wettable powder Substances 0.000 description 2
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125000002098 pyridazinyl group Chemical group 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
229940043267 rhodamine b Drugs 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
125000006413 ring segment Chemical group 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
239000012265 solid product Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000005507 spraying Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000004575 stone Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
125000004360 trifluorophenyl group Chemical group 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/34—One oxygen atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/56—One oxygen atom and one sulfur atom

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Dentistry (AREA)
Wood Science & Technology (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Agronomy & Crop Science (AREA)
General Health & Medical Sciences (AREA)
Pest Control & Pesticides (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pyridine Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

SK826-94A 1993-07-12 1994-07-11 Pyrimidinylacryle acid derivatives, method of their preparation and fungicidal compositions containt these derivatives SK82694A3 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB939314355A GB9314355D0 (en)	1993-07-12	1993-07-12	Novel compounds

Publications (1)

Publication Number	Publication Date
SK82694A3 true SK82694A3 (en)	1995-03-08

Family

ID=10738653

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK826-94A SK82694A3 (en)	1993-07-12	1994-07-11	Pyrimidinylacryle acid derivatives, method of their preparation and fungicidal compositions containt these derivatives

Country Status (21)

Country	Link
US (2)	US5453427A (ru)
EP (1)	EP0634405B1 (ru)
JP (1)	JPH0789940A (ru)
KR (1)	KR960014107A (ru)
CN (1)	CN1122800A (ru)
AT (1)	ATE226944T1 (ru)
AU (1)	AU684780B2 (ru)
BR (1)	BR9402681A (ru)
CA (1)	CA2127665A1 (ru)
CZ (1)	CZ165994A3 (ru)
DE (1)	DE69431612T2 (ru)
GB (1)	GB9314355D0 (ru)
HR (1)	HRP940398A2 (ru)
HU (1)	HU214025B (ru)
IL (1)	IL110271A (ru)
PL (1)	PL176705B1 (ru)
RU (1)	RU94026277A (ru)
SG (1)	SG45357A1 (ru)
SK (1)	SK82694A3 (ru)
TW (1)	TW267094B (ru)
ZA (1)	ZA945047B (ru)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB9400889D0 (en) *	1994-01-18	1994-03-16	Sandoz Ltd	Novel compounds
AU691673B2 (en) *	1994-11-14	1998-05-21	Dow Agrosciences Llc	Pyridazinones and their use as fungicides
US5783580A (en) *	1995-01-10	1998-07-21	Sandoz, Ltd.	α-pyrimidinyl acrylic acid derivatives
GB9504920D0 (en) *	1995-03-10	1995-04-26	Sandoz Ltd	Organic compounds
GB9519787D0 (en) *	1995-09-28	1995-11-29	Sandoz Ltd	Organic compounds
EP0882025A1 (de) *	1996-02-05	1998-12-09	Basf Aktiengesellschaft	Pyrimidinderivate, verfahren und zwischenprodukte zu ihrer herstellung und sie enthaltende mittel zur bekämpfung von tierischen schädlingen oder von schadpilzen
GB0913636D0 (en)	2009-08-05	2009-09-16	Univ Leuven Kath	Novel viral replication inhibitors

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NZ213630A (en) *	1984-10-19	1990-02-26	Ici Plc	Acrylic acid derivatives and fungicidal compositions
DE3783503T2 (de) *	1986-04-17	1993-05-13	Ici Plc	Pyridylacrylsaeureester-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide.
GB8609452D0 (en) *	1986-04-17	1986-05-21	Ici Plc	Fungicides
GB8620251D0 (en) *	1986-08-20	1986-10-01	Ici Plc	Fungicides
GB8724252D0 (en) *	1987-10-15	1987-11-18	Ici Plc	Fungicides
DE3904931A1 (de) *	1989-02-17	1990-08-23	Bayer Ag	Pyridyl-substituierte acrylsaeureester
GB8926429D0 (en) *	1989-11-22	1990-01-10	Ici Plc	Fungicides
DE4025892A1 (de) *	1990-08-16	1992-02-20	Bayer Ag	Verfahren zur herstellung von substituierten 3-aminoacrylestern
DE4025891A1 (de) *	1990-08-16	1992-02-20	Bayer Ag	Pyrimidyl-substituierte acrylsaeureester
FR2676734B1 (fr) *	1991-05-23	1995-05-19	Roussel Uclaf	Nouveaux derives de la pyrimidine, leur procede de preparation, les nouveaux intermediaires obtenus, leur application a titre de medicaments et les compositions pharmaceutiques les renfermant.
DE4142191A1 (de) *	1991-12-20	1993-06-24	Bayer Ag	Verfahren zur herstellung von 3-alkoxy-acrylestern
JP3217191B2 (ja) *	1992-07-16	2001-10-09	ビーエーエスエフアクチェンゲゼルシャフト	ヘテロ芳香族化合物およびこれを含有する植物保護剤

1993
- 1993-07-12 RU RU94026277/04A patent/RU94026277A/ru unknown
- 1993-07-12 GB GB939314355A patent/GB9314355D0/en active Pending
1994
- 1994-07-08 AT AT94810406T patent/ATE226944T1/de not_active IP Right Cessation
- 1994-07-08 EP EP94810406A patent/EP0634405B1/en not_active Expired - Lifetime
- 1994-07-08 CZ CZ941659A patent/CZ165994A3/cs unknown
- 1994-07-08 DE DE69431612T patent/DE69431612T2/de not_active Expired - Fee Related
- 1994-07-08 US US08/273,033 patent/US5453427A/en not_active Expired - Fee Related
- 1994-07-08 CA CA002127665A patent/CA2127665A1/en not_active Abandoned
- 1994-07-08 SG SG1996004492A patent/SG45357A1/en unknown
- 1994-07-11 JP JP6158403A patent/JPH0789940A/ja active Pending
- 1994-07-11 HR HR9314355.0A patent/HRP940398A2/xx not_active Application Discontinuation
- 1994-07-11 BR BR9402681A patent/BR9402681A/pt not_active IP Right Cessation
- 1994-07-11 AU AU67395/94A patent/AU684780B2/en not_active Ceased
- 1994-07-11 SK SK826-94A patent/SK82694A3/sk unknown
- 1994-07-11 CN CN94107547A patent/CN1122800A/zh active Pending
- 1994-07-11 KR KR1019940016584A patent/KR960014107A/ko not_active Application Discontinuation
- 1994-07-11 PL PL94304226A patent/PL176705B1/pl unknown
- 1994-07-11 IL IL11027194A patent/IL110271A/en not_active IP Right Cessation
- 1994-07-12 ZA ZA945047A patent/ZA945047B/xx unknown
- 1994-07-12 HU HU9402075A patent/HU214025B/hu not_active IP Right Cessation
- 1994-07-13 TW TW083106335A patent/TW267094B/zh active
1995
- 1995-05-08 US US08/435,053 patent/US5635508A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
EP0634405B1 (en)	2002-10-30
BR9402681A (pt)	1995-05-02
AU684780B2 (en)	1998-01-08
SG45357A1 (en)	1998-01-16
DE69431612D1 (de)	2002-12-05
EP0634405A1 (en)	1995-01-18
HRP940398A2 (en)	1996-12-31
HU214025B (en)	1997-12-29
HU9402075D0 (en)	1994-09-28
CZ165994A3 (en)	1995-02-15
JPH0789940A (ja)	1995-04-04
US5635508A (en)	1997-06-03
ATE226944T1 (de)	2002-11-15
IL110271A (en)	1998-09-24
PL304226A1 (en)	1995-01-23
IL110271A0 (en)	1994-10-21
US5453427A (en)	1995-09-26
AU6739594A (en)	1995-01-19
RU94026277A (ru)	1996-05-27
HUT68258A (en)	1995-06-28
GB9314355D0 (en)	1993-08-25
DE69431612T2 (de)	2003-04-03
CA2127665A1 (en)	1995-01-13
PL176705B1 (pl)	1999-07-30
CN1122800A (zh)	1996-05-22
KR960014107A (ko)	1996-05-22
ZA945047B (en)	1996-01-12
TW267094B (ru)	1996-01-01

Publication	Publication Date	Title
AU616031B2 (en)	1991-10-17	Alpha-arylacrylates substituted by a heterocyclic radical, and fungicides which contain these compounds
US5120734A (en)	1992-06-09	Fungicidal pyrid-2-yl-amino acetic acid esters
EP0471261B1 (de)	1996-01-17	Pyrimidyl-substituierte Acrylsäureester
US5547919A (en)	1996-08-20	α-pyrimidinyl acrylic acid derivatives
US5300521A (en)	1994-04-05	Pyrazoles, fungicidal compositions and use
US4954497A (en)	1990-09-04	Acrylic acid morpholides and fungicidal compositions
US5378711A (en)	1995-01-03	α-arylacrylates substituted by a heterocyclic radical, and fungicides which contain these compounds
JPH05112541A (ja)	1993-05-07	トリアジニル置換アクリル酸エステル
SK82694A3 (en)	1995-03-08	Pyrimidinylacryle acid derivatives, method of their preparation and fungicidal compositions containt these derivatives
EP0770611A2 (en)	1997-05-02	Fungicidal 2-(4-Pyrazolyloxy-pyrimidin-5-yl) acetic acid derivatives
RU2133746C1 (ru)	1999-07-27	Производные никотиновой кислоты, способ их получения и гербицидная композиция
US5776941A (en)	1998-07-07	4-alkylthio-pyrimidin-5-ylacetic acid derivates
CA2206306A1 (en)	1996-06-13	Novel pyrimidinyloxy- and pyrimidinylamino-ethylphenyl-dioxolane derivatives
US5783580A (en)	1998-07-21	α-pyrimidinyl acrylic acid derivatives
US6867212B2 (en)	2005-03-15	6-(1-fluoroethyl)-5-iodo-4-aminopyrimidine compounds process for preparation of the same and pest controllers for agricultural and horticultural use
MXPA96004347A (en)	1998-10-23	Acid derivatives 2- (4-pirazolylioxi-pirimidin-5-il) acet