CH640214A5 - CHLORACETANILIDES, METHOD FOR THE PRODUCTION OF THESE COMPOUNDS AND HERBICIDES CONTAINING THEM. - Google Patents
CHLORACETANILIDES, METHOD FOR THE PRODUCTION OF THESE COMPOUNDS AND HERBICIDES CONTAINING THEM. Download PDFInfo
- Publication number
- CH640214A5 CH640214A5 CH77479A CH77479A CH640214A5 CH 640214 A5 CH640214 A5 CH 640214A5 CH 77479 A CH77479 A CH 77479A CH 77479 A CH77479 A CH 77479A CH 640214 A5 CH640214 A5 CH 640214A5
- Authority
- CH
- Switzerland
- Prior art keywords
- chloroacetic acid
- compound according
- formula
- ch2ch2
- alkyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 43
- 238000000034 method Methods 0.000 title claims description 10
- 239000004009 herbicide Substances 0.000 title claims description 4
- -1 Cj-C4-alkyl Chemical class 0.000 claims description 27
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims description 24
- 239000004480 active ingredient Substances 0.000 claims description 13
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- VONWPEXRCLHKRJ-UHFFFAOYSA-N 2-chloro-n-phenylacetamide Chemical class ClCC(=O)NC1=CC=CC=C1 VONWPEXRCLHKRJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 150000003931 anilides Chemical class 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 5
- GZZHYQQPULZHQQ-UHFFFAOYSA-N CCOCCOCCN(C1=CC=CC=C1C)C(=O)CCl Chemical compound CCOCCOCCN(C1=CC=CC=C1C)C(=O)CCl GZZHYQQPULZHQQ-UHFFFAOYSA-N 0.000 claims description 4
- 150000001448 anilines Chemical class 0.000 claims description 4
- PAWWAVKQPZETHQ-UHFFFAOYSA-N C(C)C1=C(N(C(CCl)=O)CCOCCOCCOC)C(=CC=C1)CC Chemical compound C(C)C1=C(N(C(CCl)=O)CCOCCOCCOC)C(=CC=C1)CC PAWWAVKQPZETHQ-UHFFFAOYSA-N 0.000 claims description 3
- JOWDEDOENOSTFB-UHFFFAOYSA-N C(C)C1=C(N(C(CCl)=O)CCOCCOCC)C(=CC=C1)CC Chemical compound C(C)C1=C(N(C(CCl)=O)CCOCCOCC)C(=CC=C1)CC JOWDEDOENOSTFB-UHFFFAOYSA-N 0.000 claims description 2
- IIHZFPKRYVHKIR-UHFFFAOYSA-N C(COCCOC)N(C1=CC=CC=C1)C(CCl)=O Chemical compound C(COCCOC)N(C1=CC=CC=C1)C(CCl)=O IIHZFPKRYVHKIR-UHFFFAOYSA-N 0.000 claims description 2
- SDUOZKKOGLHILD-UHFFFAOYSA-N CC1=C(N(C(CCl)=O)CCOCCOCCOCC)C(=CC=C1)C Chemical compound CC1=C(N(C(CCl)=O)CCOCCOCCOCC)C(=CC=C1)C SDUOZKKOGLHILD-UHFFFAOYSA-N 0.000 claims description 2
- AOJVPXQFBPHDGE-UHFFFAOYSA-N ClC1=C(N(C(CCl)=O)CCOCCOC)C(=CC=C1)C Chemical compound ClC1=C(N(C(CCl)=O)CCOCCOC)C(=CC=C1)C AOJVPXQFBPHDGE-UHFFFAOYSA-N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 claims 1
- WUXZDZHIDRSCMX-UHFFFAOYSA-N C(COCCOC)N(C1=C(C=CC=C1)C)C(CCl)=O Chemical compound C(COCCOC)N(C1=C(C=CC=C1)C)C(CCl)=O WUXZDZHIDRSCMX-UHFFFAOYSA-N 0.000 claims 1
- MRYJSPXKAAQMKS-UHFFFAOYSA-N ClC1=C(N(C(CCl)=O)CCOCCOCC)C(=CC=C1)C Chemical compound ClC1=C(N(C(CCl)=O)CCOCCOCC)C(=CC=C1)C MRYJSPXKAAQMKS-UHFFFAOYSA-N 0.000 claims 1
- 229940125758 compound 15 Drugs 0.000 claims 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 claims 1
- 241000196324 Embryophyta Species 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 10
- 239000002689 soil Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 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
- 239000000969 carrier Substances 0.000 description 4
- 230000002363 herbicidal effect Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000192043 Echinochloa Species 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000001419 dependent effect Effects 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 2
- WNMSNCXTZCHCFB-UHFFFAOYSA-N CC1=C(C(=CC=C1)C)N(CCOCCOC)C(=O)CCl Chemical compound CC1=C(C(=CC=C1)C)N(CCOCCOC)C(=O)CCl WNMSNCXTZCHCFB-UHFFFAOYSA-N 0.000 description 2
- GUATZODCWUFKSM-UHFFFAOYSA-N CC1=CC=CC=C1N(CCOCCOCCOC)C(=O)CCl Chemical compound CC1=CC=CC=C1N(CCOCCOCCOC)C(=O)CCl GUATZODCWUFKSM-UHFFFAOYSA-N 0.000 description 2
- 235000017896 Digitaria Nutrition 0.000 description 2
- 241001303487 Digitaria <clam> Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- PBKGNJXLJQARIN-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethyl 4-methylbenzenesulfonate Chemical compound COCCOCCOS(=O)(=O)C1=CC=C(C)C=C1 PBKGNJXLJQARIN-UHFFFAOYSA-N 0.000 description 1
- JSIAIROWMJGMQZ-UHFFFAOYSA-N 2h-triazol-4-amine Chemical class NC1=CNN=N1 JSIAIROWMJGMQZ-UHFFFAOYSA-N 0.000 description 1
- 241000743339 Agrostis Species 0.000 description 1
- 241000234282 Allium Species 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 235000017060 Arachis glabrata Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000018262 Arachis monticola Nutrition 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- 240000002791 Brassica napus Species 0.000 description 1
- 240000007124 Brassica oleracea Species 0.000 description 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000011299 Brassica oleracea var botrytis Nutrition 0.000 description 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- 240000003259 Brassica oleracea var. botrytis Species 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241000209200 Bromus Species 0.000 description 1
- PMHUNDGCXLITTR-UHFFFAOYSA-N CC1=C(C(=CC=C1)C)N(CCOCCOCCOC)C(=O)CCl Chemical compound CC1=C(C(=CC=C1)C)N(CCOCCOCCOC)C(=O)CCl PMHUNDGCXLITTR-UHFFFAOYSA-N 0.000 description 1
- YYCPJPSLQCQBEF-UHFFFAOYSA-N CC1=C(N(C(CCl)=O)CCOCCOCC)C(=CC=C1)C Chemical compound CC1=C(N(C(CCl)=O)CCOCCOCC)C(=CC=C1)C YYCPJPSLQCQBEF-UHFFFAOYSA-N 0.000 description 1
- ALERPWCQEYALPL-UHFFFAOYSA-N CCOCCOCCOCCOCCN(C1=C(C=CC=C1C)C)C(=O)CCl Chemical compound CCOCCOCCOCCOCCN(C1=C(C=CC=C1C)C)C(=O)CCl ALERPWCQEYALPL-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 244000192528 Chrysanthemum parthenium Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241000234653 Cyperus Species 0.000 description 1
- 241000209210 Dactylis Species 0.000 description 1
- 240000001879 Digitalis lutea Species 0.000 description 1
- 244000152970 Digitaria sanguinalis Species 0.000 description 1
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 1
- 244000058871 Echinochloa crus-galli Species 0.000 description 1
- 241000234642 Festuca Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 241000219146 Gossypium Species 0.000 description 1
- 240000008415 Lactuca sativa Species 0.000 description 1
- 235000003228 Lactuca sativa Nutrition 0.000 description 1
- 241000209510 Liliopsida Species 0.000 description 1
- 235000019738 Limestone Nutrition 0.000 description 1
- 241000209082 Lolium Species 0.000 description 1
- 235000017945 Matricaria Nutrition 0.000 description 1
- 235000007232 Matricaria chamomilla Nutrition 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 235000011999 Panicum crusgalli Nutrition 0.000 description 1
- 241001325197 Phacelia Species 0.000 description 1
- 241000746981 Phleum Species 0.000 description 1
- 235000010582 Pisum sativum Nutrition 0.000 description 1
- 240000004713 Pisum sativum Species 0.000 description 1
- 241000209048 Poa Species 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 241000205407 Polygonum Species 0.000 description 1
- 241000780602 Senecio Species 0.000 description 1
- 235000005775 Setaria Nutrition 0.000 description 1
- 241000232088 Setaria <nematode> Species 0.000 description 1
- 241000207763 Solanum Species 0.000 description 1
- 235000002634 Solanum Nutrition 0.000 description 1
- 240000006394 Sorghum bicolor Species 0.000 description 1
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 1
- 244000300264 Spinacia oleracea Species 0.000 description 1
- 235000009337 Spinacia oleracea Nutrition 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- 241000219793 Trifolium Species 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- XCSGPAVHZFQHGE-UHFFFAOYSA-N alachlor Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl XCSGPAVHZFQHGE-UHFFFAOYSA-N 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 150000001559 benzoic acids Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 150000004891 diazines Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 241001233957 eudicotyledons Species 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000003864 humus Substances 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 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 1
- 239000006028 limestone Substances 0.000 description 1
- 210000001699 lower leg Anatomy 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- OLUJCJYUWPCYNM-UHFFFAOYSA-N n-[2-(2-methoxyethoxy)ethyl]-2,6-dimethylaniline Chemical compound COCCOCCNC1=C(C)C=CC=C1C OLUJCJYUWPCYNM-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 231100001184 nonphytotoxic Toxicity 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 210000002741 palatine tonsil Anatomy 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000008379 phenol ethers Chemical class 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000021749 root development Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical class NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
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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
- 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
- A01N37/18—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 the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/22—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 the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
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- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Die Erfindung betrifft neue Chloracetanilide, Verfahren zur Herstellung dieser Verbindungen sowie herbizide Mittel, The invention relates to new chloroacetanilides, processes for the preparation of these compounds and herbicidal compositions,
(I) , (I),
enthaltend mindestens eine dieser Verbindungen als Wirkstoffkomponente. containing at least one of these compounds as an active ingredient.
Halogenacetanilid-Derivate mit herbizider Wirkung sind 30 bereits bekannt (siehe US-PS 3 547 620). Diese besitzen jedoch ein nur enges Wirkungsspektrum und sind in ihrer Wirkung stark bodenabhängig. Haloacetanilide derivatives with herbicidal activity are already known (see US Pat. No. 3,547,620). However, these have only a narrow spectrum of activity and their effects are strongly dependent on the soil.
Aufgabe der vorliegenden Erfindung ist daher die Entwicklung neuer, herbizid aktiver Verbindungen, welche ein 35 breites Wirkungsspektrum besitzen und nicht bodenabhängig sind. The object of the present invention is therefore the development of new, herbicidally active compounds which have a broad spectrum of activity and are not soil-dependent.
Die neuen, herbizid aktiven Verbindungen weisen die folgende Formel auf x ch2ch2 - (0ch2ch2)n - 0r4 The new herbicidally active compounds have the following formula: x ch2ch2 - (0ch2ch2) n - 0r4
cch^cl fi 2 cch ^ cl fi 2
(i), (i),
in der Rl5 R2 und R3 gleich oder verschieden sind und Wasserstoff, Cj-C4-Alkyl, Halogen oder Trifluormethyl, R4 Cj-Cg-Alkyl und n die Zahlen 1,2 oder 3 darstellen. in which Rl5 R2 and R3 are the same or different and represent hydrogen, Cj-C4-alkyl, halogen or trifluoromethyl, R4 Cj-Cg-alkyl and n represent the numbers 1, 2 or 3.
Das herbizide Mittel ist dadurch gekennzeichnet, dass es als Wirkstoffkomponente mindestens eine neue Verbindung der weiter oben angegebenen Formel I enthält. The herbicidal composition is characterized in that it contains at least one new compound of the formula I given above as the active ingredient.
Die gekennzeichneten Verbindungen bzw. das Mittel zeichnen sich durch eine breite bodenherbizide Wirkung aus. Sie können zur Bekämpfung mono- und dikotyler Unkräuter verwendet werden. The labeled compounds or the agent are characterized by a broad soil herbicidal action. They can be used to control mono- and dicotyledon weeds.
Bei den Verbindungen können im Vorauflaufverfahren Unkräuter wie Allium, Solanum, Senecio, Matricaria, Ga-lium, Polygonum, Trifolium, Escholtzia, Digitalis, Phacelia, Sorghum, Echinochloa, Setaria, Digitaris, Cyperus, Poa, Agrostis, Bromus, Lolium, Phleum, Dactylis, Festuca und andere Unkräuter bekämpft werden. For the compounds, weeds such as Allium, Solanum, Senecio, Matricaria, Ga-lium, Polygonum, Trifolium, Escholtzia, Digitalis, Phacelia, Sorghum, Echinochloa, Setaria, Digitaris, Cyperus, Poa, Agrostis, Bromus, Lolium, Phleum, Dactylis, Festuca and other weeds are controlled.
Zur Bekämpfung von Unkräutern werden in der Regel Aufwandmengen von 0,5 kg Wirkstoff/ha bis 5 kg Wirkstoff/ha verwendet. Dabei erweisen sich die gekennzeich50 To control weeds, application rates of 0.5 kg of active ingredient / ha to 5 kg of active ingredient / ha are generally used. The markings50 prove themselves
55 55
60 60
65 65
neten Wirkstoffe überraschenderweise auch selektiv wirksam in Nutzpflanzenkulturen, wie z.B. Baumwolle, Erdnuss, Raps, Markstammkohl, Blumenkohl, Sojabohne, Erbse, Zuckerrübe, Spinat und Salat. Surprisingly, active substances are also selectively active in crops such as Cotton, peanut, rapeseed, marrow cabbage, cauliflower, soybean, pea, sugar beet, spinach and lettuce.
Ausserdem zeigen die Wirkstoffe vorteilhafterweise wuchsregulierende Eigenschaften. In addition, the active ingredients advantageously show growth-regulating properties.
Als weitere von den erfindungsgemässen Verbindungen verursachte technisch wertvolle Entwicklungsänderungen der Pflanze seien z.B. genannt die Hemmung des vertikalen Wachstums, die Hemmung der Wurzelentwicklung, die Anregung des Knospenaustriebes oder der Bestockungstriebe, die Intensivierung der Bildung von Pflanzenfarbstoffen und die Verbesserung der Speicherfähigkeit von Pflanzeninhalt-stoffen. Further technically valuable developmental changes in the plant caused by the compounds according to the invention are e.g. called the inhibition of vertical growth, the inhibition of root development, the stimulation of bud buds or tillers, the intensification of the formation of plant dyes and the improvement of the storage capacity of plant substances.
Die erfindungsgemässen Verbindungen können entweder allein, in Mischung miteinander oder mit anderen Wirkstoffen angewendet werden. Gegebenenfalls können andere Pflanzenschutz- oder Schädlingsbekämpfungsmittel je nach dem gewünschten Zweck zugesetzt werden. The compounds according to the invention can be used either alone, in a mixture with one another or with other active ingredients. If necessary, other pesticides or pesticides can be added depending on the desired purpose.
5 5
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Sofern eine Verbreiterung des Wirkungsspektrums beabsichtigt ist, können auch andere Herbizide zugesetzt werden. Beispielsweise eignen sich als herbizid wirksame Mischungspartner Wirkstoffe aus der Gruppe der Triazine, Amino-triazole, Anilide, Diazine, Uracile, aliphatische Carbonsäuren und Halogencarbonsäuren, substituierte Benzoesäuren und Aryloxycarbonsäuren, Hydrazide, Amide, Nitrile, Ester solcher Carbonsäuren, Carbamidsäure- und Thiocarb-amidsäureester, Harnstoffe, 1,3,6-Trichlorbenzyloxy-propanil und rhodanhaltigen Mitteln u.a. Unter anderen Zusätzen sind z.B. auch nichtphytotoxische Zusätze zu verstehen, die bei Herbiziden eine synergistische Wirkungssteigerung, ergeben, wie Netzmittel, Emulgatoren, Lösungsmittel und ölige Zusätze. If it is intended to broaden the spectrum of activity, other herbicides can also be added. For example, active ingredients from the group of triazines, amino-triazoles, anilides, diazines, uracils, aliphatic carboxylic acids and halogenated carboxylic acids, substituted benzoic acids and aryloxycarboxylic acids, hydrazides, amides, nitriles, esters of such carboxylic acids, carbamic acid and thiocarbamic acid amides are suitable as herbicidally active mixture partners , Ureas, 1,3,6-trichlorobenzyloxypropanil and rhodane-containing agents, inter alia Among other additives are e.g. also to understand non-phytotoxic additives which result in a synergistic increase in activity in herbicides, such as wetting agents, emulsifiers, solvents and oily additives.
Zweckmässig werden die gekennzeichneten Wirkstoffe oder deren Mischungen in Form von Zubereitungen, wie Pulvern, Streumitteln, Granulaten, Lösungen, Emulsionen oder Suspensionen, unter Zusatz von flüssigen und/oder festen Trägerstoffen bzw. Verdünnungsmitteln und gegebenenfalls von Netz-, Haft-, Emulgier- und/oder Dispergier-hilfsmitteln, angewandt. The labeled active ingredients or mixtures thereof are expedient in the form of preparations, such as powders, sprinkling agents, granules, solutions, emulsions or suspensions, with the addition of liquid and / or solid carriers or diluents and, if appropriate, wetting agents, adhesives, emulsifiers and / or dispersing agents, applied.
Geeignete flüssige Trägerstoffe sind z.B. Wasser, aliphatische und aromatische Kohlenwasserstoffe, wie Benzol, Toluol, Xylol, Cyclohexanon, Isophoron, Dimethyl-sulfoxyd, Dimethylformamid, weiterhin Mineralölfraktionen. Suitable liquid carriers are e.g. Water, aliphatic and aromatic hydrocarbons, such as benzene, toluene, xylene, cyclohexanone, isophorone, dimethyl sulfoxide, dimethylformamide and mineral oil fractions.
Als feste Trägerstoffe eignen sich Mineralerden, z.B. Tonsil, Silicagel, Talkum, Kaolin, Attaclay, Kalkstein, Kieselsäure, und pflanzliche Produkte, z.B. Mehle. Mineral soils are suitable as solid carriers, e.g. Tonsil, silica gel, talc, kaolin, Attaclay, limestone, silica, and vegetable products, e.g. Flour.
An bevorzugten oberflächenaktiven Stoffen sind zu nennen, z.B. Calciumligninsulfonat, Polyoxyäthylen-alkyl- Preferred surfactants include, e.g. Calcium lignin sulfonate, polyoxyethylene alkyl
phenoläther, Naphthalinsulfonsäuren und deren Salze, Phenolsulfonsäuren und deren Salze, Formaldehydkondensate, Fettalkoholsulfate sowie substituierte Benzol-sulfonsäuren und deren Salze. phenol ethers, naphthalenesulfonic acids and their salts, phenolsulfonic acids and their salts, formaldehyde condensates, fatty alcohol sulfates and substituted benzene sulfonic acids and their salts.
s Der Anteil des bzw. der des Wirkstoffe(s) in den verschiedenen Zubereitungen kann in weiten Grenzen variieren. Beispielsweise enthalten die Mittel etwa 5 bis 95 Gewichtsprozente Wirkstoffe, etwa 95 bis 5 Gewichtsprozente flüssige oder feste Trägerstoffe sowie gegebenenfalls bis zu 20 Ge-io wichtsprozente oberflächenaktive Stoffe. s The proportion of the active ingredient (s) in the various preparations can vary within wide limits. For example, the agents contain about 5 to 95 percent by weight of active ingredients, about 95 to 5 percent by weight of liquid or solid carriers and optionally up to 20 percent by weight of surface-active agents.
Die Ausbringung der Mittel kann in üblicher Weise erfolgen, z.B. mit Wasser als Träger in Spritzbrühmengen von etwa 100 bis 1000 Liter/ha. Eine Anwendung der Mittel im sogenannten Low-Volume- und Ultra-low-Volume-Verfah-i5 ren ist ebenso möglich wie ihre Applikation in Form von sogenannten Mikrogranulaten. The funds can be applied in a customary manner, e.g. with water as a carrier in spray liquor quantities of about 100 to 1000 liters / ha. Use of the agents in the so-called low-volume and ultra-low-volume process is just as possible as their application in the form of so-called microgranules.
Als in der allgemeinen Formel I bezeichnete Reste Rt, R2 und R3 sind vorzugsweise zu nennen: Methyl, Äthyl, n-Propyl, Isopropyl, n-Butyl, sec.-Butyl, Isobutyl, tert.-Butyl, 20 Fluor, Chlor, Brom, Jod, Trifluormethyl. The radicals Rt, R2 and R3 designated in the general formula I should preferably be mentioned: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, 20 fluorine, chlorine, bromine , Iodine, trifluoromethyl.
Der Rest R4 kann beispielsweise bedeuten Methyl, The radical R4 can mean, for example, methyl,
Äthyl, Propyl, Isopropyl, n-Butyl, sec.-Butyl, Isobutyl, tert.-Butyl, n-Pentyl und n-hexyl. Ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl and n-hexyl.
Von den erfindungsgemässen Verbindungen zeichnen 25 sich durch eine herausragende Wirkung insbesondere solche aus, welche der allgemeinen Formel I entsprechen und worin Rx und R2 gleich oder verschieden sind und Cx-Q-Alkyl, R3 Wasserstoff, R4 C1-C4-Alkyl und n die Zahlen 1 oder 2 bedeuten. Of the compounds according to the invention, 25 have an outstanding action, in particular those which correspond to the general formula I and in which Rx and R2 are identical or different and Cx-Q-alkyl, R3 hydrogen, R4 C1-C4-alkyl and n the numbers 1 or 2 mean.
30 Die bisher nichtbekannten Verbindungen werden erfin-dungsgemäss hergestellt, indem man Aniline der Formel nh, 30 The previously unknown compounds are prepared according to the invention by using anilines of the formula nh,
Ù Ù
(ii) (ii)
Gewichtsverhältnis von 2: 1 bis 3 :1, zur Reaktion bringt, wobei die Umsetzung unter Druck, gegebenenfalls unter Zu-(III), satz von Wasser und einem Katalysator, vorzugsweise einem Nickel-Katalysator, durchgeführt wird, und das gebildete worin X Hydroxyl bedeutet, vorzugsweise in einem molaren 45 Reaktionsprodukt der Formel mit Verbindungen der Formel Weight ratio of 2: 1 to 3: 1 brings to reaction, the reaction being carried out under pressure, optionally with addition (III), of water and a catalyst, preferably a nickel catalyst, and the resultant wherein X is hydroxyl means, preferably in a molar reaction product of the formula with compounds of the formula
X-CH2CH2-(OCH2CH2)n-OR4 X-CH2CH2- (OCH2CH2) n-OR4
r„ r "
r r
—N — r, -No,
/CH2CH2 / CH2CH2
\ \
h H
(0CH2CH2)n " °R; (0CH2CH2) n "° R;
(iv) (iv)
mit Chloracetylchlorid in äquimolekularen Gewichtsverhältnissen - vorzugsweise jedoch mit einem Überschuss an Chloracetylchlorid - in Gegenwart eines Säureakzeptors, z.B. einer organischen Base, wie Pyridin oder Triäthylamin, oder einer anorganischen Base, wie Natriumhydroxid, Kaliumhydroxid, Natriumcarbonat, Kaliumcarbonat oder Magnesiumoxid, und gegebenenfalls eines organischen Lösungsmittels, bei Temperaturen von —10 bis 105 °C zu den gewünschten Verfahrensprodukten umsetzt. Diese können in an sich bekannter Weise isoliert werden. with chloroacetyl chloride in equimolecular weight ratios - but preferably with an excess of chloroacetyl chloride - in the presence of an acid acceptor, e.g. an organic base, such as pyridine or triethylamine, or an inorganic base, such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate or magnesium oxide, and optionally an organic solvent, at temperatures from -10 to 105 ° C. to give the desired process products. These can be isolated in a manner known per se.
Ein weiteres Verfahren zur Herstellung der neuen Verbindungen der Formel I ist dadurch gekennzeichnet, dass Another process for the preparation of the new compounds of the formula I is characterized in that
60 60
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man die Verbindungen der weiter oben angegebenen Formel II mit Verbindungen der Formel the compounds of the formula II given above with compounds of the formula
X'-CH2CH2-(OCH2CH2)n-OR4 (IIIA), X'-CH2CH2- (OCH2CH2) n-OR4 (IIIA),
worin X' Halogen bedeutet, vorzugsweise in einem molaren Gewichtsverhältnis von 2: 1 bis 3 : 1, zur Reaktion bringt, wobei die Umsetzung bei Temperaturen von 20 bis 200 °C, gegebenenfalls unter Verwendung eines inerten Lösungsmittels, z.B. eines organischen Lösungsmittels, wie Toluol oder Xylol, durchgeführt wird, und das gebildete Reaktionsprodukt der Formel IV, wie weiter oben beschrieben, mit Chloracetylchlorid umgesetzt wird. wherein X 'represents halogen, preferably in a molar weight ratio of 2: 1 to 3: 1, the reaction being carried out at temperatures of 20 to 200 ° C, optionally using an inert solvent, e.g. an organic solvent, such as toluene or xylene, and the reaction product of the formula IV, as described above, is reacted with chloroacetyl chloride.
640214 640214
6 6
Ein drittes Verfahren zur Herstellung der neuen Verbindungen der Formel I ist dadurch gekennzeichnet, dass man die beschriebenen Verbindungen der Formel II mit einer Verbindung der Formel A third process for the preparation of the new compounds of formula I is characterized in that the described compounds of formula II with a compound of formula
X"-CH2CH2-OCH2CH2)„-OR4 X "-CH2CH2-OCH2CH2)" - OR4
(hib), (hib),
worin X" die Gruppe 4-CH3-C6H4-S02-0- bedeutet, vorzugsweise in einem molaren Gewichtsverhältnis von 2 :1 bis 3:1, zur Reaktion bringt, wobei die Umsetzung bei Temperaturen von 20 bis 200 °C, gegebenenfalls unter Verwendung eines inerten Lösungsmittels, z.B. eines organischen Lösungsmittels, wie Toluol oder Xylol, durchgeführt wird, und das gebildete Reaktionsprodukt der Formel IV, wie bereits beschrieben, mit Chloracetylchlorid umgesetzt wird. wherein X "means the group 4-CH3-C6H4-S02-0-, preferably in a molar weight ratio of 2: 1 to 3: 1, the reaction being carried out at temperatures of 20 to 200 ° C, optionally using an inert solvent, for example an organic solvent, such as toluene or xylene, is carried out, and the reaction product of the formula IV formed, as already described, is reacted with chloroacetyl chloride.
Beispiel 1 example 1
ChIoressigsäure-[N-(3,6-dioxaheptyl)-2,6-dimethylanilid] Chloroacetic acid- [N- (3,6-dioxaheptyl) -2,6-dimethylanilide]
Eine Lösung von 60,50 g (0,5 Mol) 2,6-Dimethylanilin und 68,50 g (0,25 Mol) (p-Tolyl)-(l,4,7-trioxaoctyl)-sulfon in 100 ml Toluol wird 20 Stunden unter Rückfluss erhitzt. A solution of 60.50 g (0.5 mol) of 2,6-dimethylaniline and 68.50 g (0.25 mol) of (p-tolyl) - (l, 4,7-trioxaoctyl) sulfone in 100 ml of toluene is heated under reflux for 20 hours.
Nach dem Erkalten wird mit Wasser und 25 ml konzentrierter Natronlauge versetzt und die organische Phase nach Verdünnen mit Essigester abgetrennt. Anschliessend wird mit After cooling, water and 25 ml of concentrated sodium hydroxide solution are added, and the organic phase is separated off after dilution with ethyl acetate. Then with
Wasser fast neutral gewaschen, unter Magnesiumsulfat getrocknet und nach dem Filtrieren im Vakuum eingeengt. Man destilliert den Rückstand im Vakuum und erhält das N-(3,6-Dioxaheptyl)-2,6-dimethyIaniIin beim Siedeintervall 5 119-131 °C (0,4 Torr) Washed water almost neutral, dried under magnesium sulfate and concentrated in vacuo after filtering. The residue is distilled in vacuo and the N- (3,6-dioxaheptyl) -2,6-dimethylamine is obtained at the boiling interval 5 119 ° -131 ° C. (0.4 Torr)
Ausbeute: 32,44 g = 58,1% der Theorie. Yield: 32.44 g = 58.1% of theory.
In eine Lösung von 11,15 g (0,05 Mol) N-(3,6-Dioxahep-tyl)-2,6-dimethylanilin in 50 ml Essigester werden 13,82 g (0,1 Mol) wasserfreies Kaliumcarbonat eingetragen. Zu der io gerührten Suspension tropft man bei 25-30 °C unter Eiskühlung 11,19 g (0,1 Mol) Chloracetylchlorid zu und lässt eine Stunde nachrühren. Die Mischung wird noch einige Stunden bei Raumtemperatur belassen. Anschliessend wird mit Wasser versetzt und mehrmals mit Essigester ausgeschüttelt. Die 15 vereinigten Essigesterphasen werden über Magnesiumsulfat getrocknet und nach Filtrieren im Vakuum eingeengt. 13.82 g (0.1 mol) of anhydrous potassium carbonate are introduced into a solution of 11.15 g (0.05 mol) of N- (3,6-dioxaheptyl) -2,6-dimethylaniline in 50 ml of ethyl acetate. 11.19 g (0.1 mol) of chloroacetyl chloride are added dropwise to the io stirred suspension at 25-30 ° C. with ice cooling and the mixture is stirred for one hour. The mixture is left at room temperature for a few hours. Then water is added and the mixture is shaken out several times with ethyl acetate. The 15 combined ethyl acetate phases are dried over magnesium sulfate and, after filtering, concentrated in vacuo.
Nach dem Trocknen im Hochvakuum bei Raumtemperatur erhält man ein fast farbloses Öl. After drying in a high vacuum at room temperature, an almost colorless oil is obtained.
Ausbeute: 12,23 g = 81,6% der Theorie Yield: 12.23 g = 81.6% of theory
20 20th
Chloressigsäure-[N-(3,6-dioxaheptyl)-2,6-dimethylanilid] nD20 = 1,5250 Chloroacetic acid- [N- (3,6-dioxaheptyl) -2,6-dimethylanilide] nD20 = 1.5250
In analoger Weise lassen sich auch die folgenden erfin-25 dungsgemässen Verbindungen herstellen. The following compounds according to the invention can also be prepared in an analogous manner.
Name der Verbindung Name of the connection
Physikalische Konstante Physical constant
Chloressigsäure-[N-(3,6-dioxaoctyl)-2-methylanilid] Chloroacetic acid- [N- (3,6-dioxaoctyl) -2-methylanilide]
nD20 nd20
= =
1,5108 1.5108
Chloressigsäure-[N-(3,6-dioxaheptyl)-anilid] Chloroacetic acid- [N- (3,6-dioxaheptyl) anilide]
nD20 nd20
= =
1,5260 1.5260
Chloressigsäure-[2,6-diäthyI-N-(3,6-dioxaheptyI)-anilid] Chloroacetic acid- [2,6-diethyI-N- (3,6-dioxaheptyI) anilide]
nD20 nd20
= =
1,5214 1.5214
Chloressigsäure-[N-(3,6-dioxaheptyl)-2-methyl-anilid} Chloroacetic acid- [N- (3,6-dioxaheptyl) -2-methyl-anilide}
nD20 nd20
= =
1,5212 1.5212
ChIoressigsäure-[N-(3,6-dioxaoctyl)-2,6-dimethylanilid] Chloroacetic acid- [N- (3,6-dioxaoctyl) -2,6-dimethylanilide]
nD20 nd20
: - : -
1,5200 1.5200
Chloressigsäure-[2,6-diäthyl-N-(3,6-dioxaoctyl)-anilid] Chloroacetic acid- [2,6-diethyl-N- (3,6-dioxaoctyl) anilide]
no20 no20
= =
1,5176 1.5176
ChIoressigsäure-[2-chlor-N-(3,6-dioxaheptyI)-6-methyl-anilid] Chloroacetic acid- [2-chloro-N- (3,6-dioxaheptyI) -6-methyl-anilide]
np20 np20
= =
1,5252 1.5252
Chloressigsäure-[2,chlor-N-(3,6-dioxaheptyl)-6-methyl-anilid] Chloroacetic acid- [2, chloro-N- (3,6-dioxaheptyl) -6-methyl-anilide]
nD20 nd20
= =
1,5315 1.5315
Chloressigsäure-[N-(3,6-dioxaoctyl)-2-methyIanilid] Chloroacetic acid- [N- (3,6-dioxaoctyl) -2-methylanilide]
nD20 nd20
= =
1,5092 1,5092
ChIoressigsäure-[2,6-dimethyl-N-(3,6,9-trioxadecyl)-anilidJ Chloroacetic acid- [2,6-dimethyl-N- (3,6,9-trioxadecyl) anilideJ
nD20 nd20
= =
1,5208 1.5208
ChIoressigsäure-[2,6-diäthyl-N-(3,6,9-trioxadecyl)-anilid] Chloroacetic acid- [2,6-diethyl-N- (3,6,9-trioxadecyl) anilide]
nD20 nd20
= =
1,5190 1.5190
Chloressigsäure-[2-methyI-N-(3,6,9-trioxadecyl)-anilid] Chloroacetic acid- [2-methyl-N- (3,6,9-trioxadecyl) anilide]
nD2a nD2a
= =
1,5200 1.5200
ChIoressigsäure-[2,6-dimethyl-N-(3,6,9,12-tetraoxatetra-decyl)-anilidJ Chloroacetic acid- [2,6-dimethyl-N- (3,6,9,12-tetraoxatetra-decyl) anilideJ
nD20 nd20
= =
1,5104 1.5104
Chloressigsäure-[2,6-dimethyI-N-(3,6,9-trioxaundecyl)-aniIid] Chloroacetic acid- [2,6-dimethyI-N- (3,6,9-trioxaundecyl) -aniIid]
nD20 nd20
= =
1,5140 1.5140
Chloressigsäure-[2-äthyI-6-methyl-N-(3,6-dioxaheptyl)-anilidl no20 Chloroacetic acid- [2-ethyI-6-methyl-N- (3,6-dioxaheptyl) anilidl no20
1,5225 1.5225
Die erfindungsgemässen Verbindungen stellen in der Regel nahezu farblose, geruchlose, schwerbewegliche Flüssigkeiten dar, die in polaren organischen Lösungsmitteln, wie z.B. Aceton, Dimethylformamid und Dimethylsulfoxid gut löslich, in Wasser und Benzin fast unlöslich sind. The compounds according to the invention are generally almost colorless, odorless, difficult-to-move liquids which are found in polar organic solvents, such as e.g. Acetone, dimethylformamide and dimethyl sulfoxide are readily soluble, almost insoluble in water and petrol.
Die folgenden Beispiele dienen zur Erläuterung der Anwendungsmöglichkeiten und der überlegenen Wirkungsweise der erfindungsgemässen Verbindungen. The following examples serve to explain the possible uses and the superior mode of action of the compounds according to the invention.
Beispiel 2 Example 2
Im Gewächshaus wurden die in der Tabelle aufgeführten In the greenhouse, those listed in the table were
45 erfindungsgemässen Verbindungen in einer Aufwandmenge von 3 kg Wirkstoff/ha, emulgiert in 500 Litern Wasser/ha, auf Digitaria s. und Echinochloa c.g. als Testpflanzen im Vorlaufverfahren gespritzt. Drei Wochen nach der Behandlung wurde das Behandlungsergebnis bonitiert, wobei so 45 compounds according to the invention at a rate of 3 kg of active ingredient / ha, emulsified in 500 liters of water / ha, on Digitaria s. and Echinochloa c.g. sprayed as test plants in the preliminary process. The treatment result was rated three weeks after the treatment, whereby so
0 = keine Wirkung und 4 = Vernichtung der Pflanzen bedeutet. Wie aus der Tabelle ersichtlich wird, wurde eine 55 Vernichtung der Testpflanzen erreicht. 0 = no effect and 4 = destruction of plants. As can be seen from the table, the test plants were destroyed.
Erfmdungsgemässe Verbindungen Digitaria Echinochloa sanguinalis crus galli Compounds according to the invention Digitaria Echinochloa sanguinalis crus galli
ChIoressigsäure-[N-(3,6-dioxaheptyl)-2,6-dimethylanilidJ 4 4 Chloroacetic acid- [N- (3,6-dioxaheptyl) -2,6-dimethylanilideJ 4 4
ChIoressigsäure-2,6-diäthyl-[N-(3,6-dioxaheptyl)-anilidJ 4 4 Chloroacetic acid-2,6-diethyl- [N- (3,6-dioxaheptyl) anilideJ 4 4
Chloressigsäure-[N-(3,6-dioxaheptyI)-2-methyIaniIidJ 4 4 Chloroacetic acid- [N- (3,6-dioxaheptyI) -2-methyIaniIidJ 4 4
ChIoressigsäure-[N-(3J6-dioxaoctyl)-2,6-dimethyIanilid] 4 4 Chloroacetic acid- [N- (3J6-dioxaoctyl) -2,6-dimethylanilide] 4 4
ChIoressigsäure-[2,6-diäthyI-N-(3,6-dioxaoctyl)-aniIid} 4 4 Chloroacetic acid- [2,6-diethyl-N- (3,6-dioxaoctyl) -aniIid} 4 4
Chloressigsäure-[2-chlor-N-(3,6-dioxaoctyI)-6-methyI-anilidl 4 4 Chloroacetic acid- [2-chloro-N- (3,6-dioxaoctyI) -6-methyl-anilidl 4 4
Chloressigsäure-[2-chlor-N-(3,6-dioxaheptyl)-6-methyl-anilid] 4 4 Chloroacetic acid- [2-chloro-N- (3,6-dioxaheptyl) -6-methyl-anilide] 4 4
Chloressigsäure-[N-(3,6-dioxaoctyl)-2-methyIanilidJ 4 4 Chloroacetic acid- [N- (3,6-dioxaoctyl) -2-methylanilide 4 4
7 7
(Fortsetzung) (Continuation)
640 214 640 214
Erfmdungsgemässe Verbindungen Connections according to the invention
Digitaria sanguinalis Digitaria sanguinalis
Echinochloa crus galli Echinochloa crus galli
Chloressigsäure-[2,6-dimethyl-N-(3,6,9-trioxadecyl)-anilid] Chloroacetic acid- [2,6-dimethyl-N- (3,6,9-trioxadecyl) anilide]
ChIoressigsäure-[2,6-diäthyl-N-(3,6,9-trioxadecyl)-anilid] Chloroacetic acid- [2,6-diethyl-N- (3,6,9-trioxadecyl) anilide]
Chloressigsäure-[2-methyl-N-(3,6,9-trioxadecyl)-anilid] Chloroacetic acid- [2-methyl-N- (3,6,9-trioxadecyl) anilide]
Chloressigsäure-[2,6-dimethyl-N-(3,6,9,12-tetraoxatetradecyl)-anilid] Chloroacetic acid- [2,6-dimethyl-N- (3,6,9,12-tetraoxatetradecyl) anilide]
ChIoressigsäure-[2,6-dimethyl-N-(3,6,9-trioxaundecyl)-anilid] Chloroacetic acid- [2,6-dimethyl-N- (3,6,9-trioxaundecyl) anilide]
Chloressigsäure-(2-äthyl-6-methyI-N-)3,6-dioxaheptyl)-anilid Chloroacetic acid- (2-ethyl-6-methyl-N-) 3,6-dioxaheptyl) anilide
Unbehandelt Untreated
4 4 4 4 4 4 0 4 4 4 4 4 4 0
4 4 4 4 4 4 0 4 4 4 4 4 4 0
Beispiel 3 Example 3
Im Gewächshaus wurden zwei verschiedene Bodenarten nach Einsaat der aufgeführten Pflanzen und vor deren Auflaufen mit den aufgeführten Mitteln in einer Aufwandmenge von 1 kg Wirkstoff/ha behandelt. Die Mittel wurden zu diesem Zweck gleichmässig über die Pflanzen versprüht. Hierbei zeigte 3 Wochen nach der Behandlung bei minimaler Bodenabhängigkeit der Wirkung das erfmdungsgemässe Mittel überraschend eine hohe Selektivität bei ausgezeichneter Wirkung gegen das Unkraut. Das Vergleichsmittel zeigte eine 2o vergleichsweise viel geringere Wirkung die darüber hinaus stärker abhängig von der Bodenart war. Two different types of soil were treated in the greenhouse after the plants listed had been sown and before they emerged with the listed agents at a rate of 1 kg of active ingredient / ha. For this purpose, the agents were sprayed evenly over the plants. 3 weeks after the treatment, the agent according to the invention surprisingly showed a high selectivity with an excellent action against the weeds with minimal soil dependence of the action. The comparative agent showed a comparatively much smaller effect, which was more dependent on the type of soil.
Erfmdungsgemässe Mittel o Means according to the invention o
CO CO
o S S o S S
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Chloressigsäure-[N-(3,6-dioxaheptyl)-2,6-dimethylaniIid] Chloroacetic acid- [N- (3,6-dioxaheptyl) -2,6-dimethylaniide]
humoseErde 10 10 10 10 10 10 10 10 10 10 3 2 2 0 0 0 0 0 0 0 0 0 humose earth 10 10 10 10 10 10 10 10 10 10 3 2 2 0 0 0 0 0 0 0 0 0
humusarme Erde 10 10 10 10 10 10 10 10 10 10 2 1 1 0 0 0 0 0 0 0 0 0 humus-poor earth 10 10 10 10 10 10 10 10 10 10 2 1 1 0 0 0 0 0 0 0 0 0
Vergleichsmittel (gemäss US-PS 3 547 620) Chloressigsäure-[2,6-diäthyl-N-(methoxymethyl)-anilid] Comparative agent (according to US Pat. No. 3,547,620) chloroacetic acid- [2,6-diethyl-N- (methoxymethyl) anilide]
humose Erde humusarme Erde humus poor soil
10 10 10 10 10 10 10 10 10 8 10 10 10 10 10 10 10 10 10 10 8 10
10 10 10 7 8 6 10 10 10 7 8 6
8 4 8 4
2 0 2 0
10 4 10 4
10 0 10 0
0 0 0 0
Unbehandelt humose Erde humusarme Erde Untreated humic soil poor soil
10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10
s s
Claims (18)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782803662 DE2803662A1 (en) | 1978-01-25 | 1978-01-25 | CHLORACETANILIDES, METHOD FOR PRODUCING THESE COMPOUNDS AND HERBICIDES CONTAINING THEM |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH640214A5 true CH640214A5 (en) | 1983-12-30 |
Family
ID=6030587
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH77479A CH640214A5 (en) | 1978-01-25 | 1979-01-25 | CHLORACETANILIDES, METHOD FOR THE PRODUCTION OF THESE COMPOUNDS AND HERBICIDES CONTAINING THEM. |
Country Status (37)
| Country | Link |
|---|---|
| JP (1) | JPS54106437A (en) |
| AR (1) | AR229464A1 (en) |
| AT (1) | AT363275B (en) |
| AU (1) | AU518222B2 (en) |
| BE (1) | BE873708A (en) |
| BG (1) | BG30163A3 (en) |
| BR (1) | BR7900426A (en) |
| CA (1) | CA1100996A (en) |
| CH (1) | CH640214A5 (en) |
| CS (1) | CS202520B2 (en) |
| DD (1) | DD141448A5 (en) |
| DE (1) | DE2803662A1 (en) |
| DK (1) | DK542378A (en) |
| EG (1) | EG13684A (en) |
| ES (1) | ES476140A1 (en) |
| FI (1) | FI790133A (en) |
| FR (1) | FR2415624A1 (en) |
| GB (1) | GB2013188B (en) |
| GR (1) | GR72999B (en) |
| HU (1) | HU176616B (en) |
| IE (1) | IE48057B1 (en) |
| IL (1) | IL56451A (en) |
| IN (1) | IN150409B (en) |
| IT (1) | IT1110982B (en) |
| LU (1) | LU80683A1 (en) |
| MX (1) | MX5406E (en) |
| NL (1) | NL7811673A (en) |
| NO (1) | NO150039C (en) |
| NZ (1) | NZ189424A (en) |
| PL (1) | PL112862B1 (en) |
| PT (1) | PT69111A (en) |
| RO (1) | RO76590A (en) |
| SE (1) | SE7900647L (en) |
| SU (2) | SU1149858A3 (en) |
| TR (1) | TR20274A (en) |
| YU (1) | YU304478A (en) |
| ZA (1) | ZA79319B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA828914B (en) * | 1980-03-25 | 1983-02-23 | Monsanto Co | Herbicidal 2-haloacetanilides |
| US4731109A (en) * | 1980-03-25 | 1988-03-15 | Monsanto Company | Herbicidal 2-haloacetanilides |
| EP0174278B1 (en) * | 1984-09-03 | 1989-04-19 | Ciba-Geigy Ag | N-(substituted-alkyl) dichloroacetamide derivatives |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3547620A (en) | 1969-01-23 | 1970-12-15 | Monsanto Co | N-(oxamethyl)alpha-halo-acetanilide herbicides |
| GB1407205A (en) * | 1971-09-17 | 1975-09-24 | Girling Ltd | Vehicle braking systems |
| JPS5614083B2 (en) * | 1972-02-07 | 1981-04-02 | ||
| DD112988A5 (en) * | 1972-06-06 | 1975-05-12 |
-
1978
- 1978-01-25 DE DE19782803662 patent/DE2803662A1/en not_active Withdrawn
- 1978-11-28 NL NL7811673A patent/NL7811673A/en not_active Application Discontinuation
- 1978-11-30 DK DK542378A patent/DK542378A/en not_active Application Discontinuation
- 1978-12-04 IN IN873/DEL/78A patent/IN150409B/en unknown
- 1978-12-15 AR AR274824A patent/AR229464A1/en active
- 1978-12-19 ES ES476140A patent/ES476140A1/en not_active Expired
- 1978-12-20 LU LU80683A patent/LU80683A1/en unknown
- 1978-12-22 YU YU03044/78A patent/YU304478A/en unknown
-
1979
- 1979-01-08 MX MX797634U patent/MX5406E/en unknown
- 1979-01-11 BG BG042036A patent/BG30163A3/en unknown
- 1979-01-11 IT IT19218/79A patent/IT1110982B/en active
- 1979-01-15 GB GB7901378A patent/GB2013188B/en not_active Expired
- 1979-01-16 JP JP230079A patent/JPS54106437A/en active Granted
- 1979-01-16 FI FI790133A patent/FI790133A/en unknown
- 1979-01-18 IL IL56451A patent/IL56451A/en unknown
- 1979-01-18 NZ NZ189424A patent/NZ189424A/en unknown
- 1979-01-18 CS CS79410A patent/CS202520B2/en unknown
- 1979-01-19 CA CA319,949A patent/CA1100996A/en not_active Expired
- 1979-01-22 PT PT7969111A patent/PT69111A/en unknown
- 1979-01-23 PL PL1979212939A patent/PL112862B1/en unknown
- 1979-01-23 RO RO7996564A patent/RO76590A/en unknown
- 1979-01-23 DD DD79210593A patent/DD141448A5/en unknown
- 1979-01-23 EG EG45/79A patent/EG13684A/en active
- 1979-01-24 AT AT0050579A patent/AT363275B/en not_active IP Right Cessation
- 1979-01-24 HU HU79SCHE671A patent/HU176616B/en unknown
- 1979-01-24 NO NO790230A patent/NO150039C/en unknown
- 1979-01-24 SE SE7900647A patent/SE7900647L/en not_active Application Discontinuation
- 1979-01-24 GR GR58173A patent/GR72999B/el unknown
- 1979-01-24 BR BR7900426A patent/BR7900426A/en unknown
- 1979-01-24 TR TR20274A patent/TR20274A/en unknown
- 1979-01-24 AU AU43613/79A patent/AU518222B2/en not_active Ceased
- 1979-01-25 ZA ZA79319A patent/ZA79319B/en unknown
- 1979-01-25 BE BE0/193074A patent/BE873708A/en not_active IP Right Cessation
- 1979-01-25 CH CH77479A patent/CH640214A5/en not_active IP Right Cessation
- 1979-01-25 SU SU792715499A patent/SU1149858A3/en active
- 1979-01-25 FR FR7901877A patent/FR2415624A1/en active Granted
- 1979-01-25 SU SU792713492A patent/SU886736A3/en active
- 1979-01-30 IE IE127/79A patent/IE48057B1/en unknown
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