DE3404401C2 - Verwendung von Aryloxy-Verbindungen als Antidots - Google Patents
Verwendung von Aryloxy-Verbindungen als AntidotsInfo
- Publication number
- DE3404401C2 DE3404401C2 DE3404401A DE3404401A DE3404401C2 DE 3404401 C2 DE3404401 C2 DE 3404401C2 DE 3404401 A DE3404401 A DE 3404401A DE 3404401 A DE3404401 A DE 3404401A DE 3404401 C2 DE3404401 C2 DE 3404401C2
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- phenyl
- halogen
- phenoxy
- alkoxy
- 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.)
- Expired - Lifetime
Links
- 125000004104 aryloxy group Chemical group 0.000 title description 4
- 239000004009 herbicide Substances 0.000 claims description 36
- 230000002363 herbicidal effect Effects 0.000 claims description 22
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 150000002367 halogens Chemical group 0.000 claims description 20
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 16
- -1 methoxyethoxyethoxy Chemical group 0.000 claims description 16
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 230000000694 effects Effects 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 231100000208 phytotoxic Toxicity 0.000 claims description 4
- 230000000885 phytotoxic effect Effects 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 150000001768 cations Chemical class 0.000 claims description 3
- BADXJIPKFRBFOT-UHFFFAOYSA-N dimedone Chemical class CC1(C)CC(=O)CC(=O)C1 BADXJIPKFRBFOT-UHFFFAOYSA-N 0.000 claims description 3
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 2
- 125000006536 (C1-C2)alkoxy group Chemical group 0.000 claims description 2
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 2
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 2
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- VAIZTNZGPYBOGF-UHFFFAOYSA-N butyl 2-(4-{[5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoate Chemical compound C1=CC(OC(C)C(=O)OCCCC)=CC=C1OC1=CC=C(C(F)(F)F)C=N1 VAIZTNZGPYBOGF-UHFFFAOYSA-N 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- OSUHJPCHFDQAIT-UHFFFAOYSA-N ethyl 2-{4-[(6-chloroquinoxalin-2-yl)oxy]phenoxy}propanoate Chemical compound C1=CC(OC(C)C(=O)OCC)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 OSUHJPCHFDQAIT-UHFFFAOYSA-N 0.000 claims description 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 150000007529 inorganic bases Chemical class 0.000 claims description 2
- MFSWTRQUCLNFOM-UHFFFAOYSA-N methyl 2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoate Chemical compound C1=CC(OC(C)C(=O)OC)=CC=C1OC1=NC=C(C(F)(F)F)C=C1Cl MFSWTRQUCLNFOM-UHFFFAOYSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 235000015097 nutrients Nutrition 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- ASALLPQQHGTWEF-UHFFFAOYSA-N prop-2-ynyl 2-[4-(3,5-dichloropyridin-2-yl)oxyphenoxy]propanoate Chemical compound C1=CC(OC(C)C(=O)OCC#C)=CC=C1OC1=NC=C(Cl)C=C1Cl ASALLPQQHGTWEF-UHFFFAOYSA-N 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 2
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 claims 1
- 150000001733 carboxylic acid esters Chemical class 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 235000019260 propionic acid Nutrition 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 17
- 239000004480 active ingredient Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 8
- 239000000729 antidote Substances 0.000 description 7
- 230000009931 harmful effect Effects 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 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 5
- 241000209140 Triticum Species 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 229920000151 polyglycol Polymers 0.000 description 5
- 239000010695 polyglycol Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 240000007594 Oryza sativa Species 0.000 description 4
- 235000007164 Oryza sativa Nutrition 0.000 description 4
- 235000021307 Triticum Nutrition 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 239000004495 emulsifiable concentrate Substances 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 235000009566 rice Nutrition 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 240000005979 Hordeum vulgare Species 0.000 description 3
- 235000007340 Hordeum vulgare Nutrition 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 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 3
- 239000000463 material Substances 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 239000005995 Aluminium silicate Substances 0.000 description 2
- 241000209761 Avena Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical class C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 239000003337 fertilizer Substances 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000009331 sowing Methods 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 description 1
- DWDIDIITNMWCKN-UHFFFAOYSA-N 2-(N-ethoxy-C-propylcarbonimidoyl)-3-hydroxy-5-(2-phenylsulfanylpropyl)cyclohex-2-en-1-one Chemical compound C1C(=O)C(C(=NOCC)CCC)=C(O)CC1CC(C)SC1=CC=CC=C1 DWDIDIITNMWCKN-UHFFFAOYSA-N 0.000 description 1
- CMJUNAQINNWKAU-KTKRTIGZSA-N 2-[[(z)-2-oxononadec-10-enyl]amino]ethanesulfonic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)CNCCS(O)(=O)=O CMJUNAQINNWKAU-KTKRTIGZSA-N 0.000 description 1
- FOGYNLXERPKEGN-UHFFFAOYSA-N 3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfopropyl)phenoxy]propane-1-sulfonic acid Chemical compound COC1=CC=CC(CC(CS(O)(=O)=O)OC=2C(=CC(CCCS(O)(=O)=O)=CC=2)OC)=C1O FOGYNLXERPKEGN-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 241000743985 Alopecurus Species 0.000 description 1
- 235000007320 Avena fatua Nutrition 0.000 description 1
- 241000209764 Avena fatua Species 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-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
- 239000005909 Kieselgur Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 241000209504 Poaceae Species 0.000 description 1
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- 241000209056 Secale Species 0.000 description 1
- 235000007238 Secale cereale Nutrition 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 240000006394 Sorghum bicolor Species 0.000 description 1
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- YQSGAPRTTCXZBP-UHFFFAOYSA-N [2-(1,3-benzothiazol-2-yloxy)phenyl] hydrogen carbonate Chemical class OC(=O)OC1=CC=CC=C1OC1=NC2=CC=CC=C2S1 YQSGAPRTTCXZBP-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 229940075522 antidotes Drugs 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000002785 azepinyl group Chemical group 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- CSPPKDPQLUUTND-UHFFFAOYSA-N chembl3186232 Chemical compound CCON=C(CCC)C1=C(O)CC(CC(C)SCC)CC1=O CSPPKDPQLUUTND-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229940071161 dodecylbenzenesulfonate Drugs 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052622 kaolinite Inorganic materials 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000017066 negative regulation of growth Effects 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 229920002113 octoxynol Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 239000004476 plant protection product Substances 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920001522 polyglycol ester Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- BGRYSGVIVVUJHH-UHFFFAOYSA-N prop-2-ynyl propanoate Chemical compound CCC(=O)OCC#C BGRYSGVIVVUJHH-UHFFFAOYSA-N 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000005554 pyridyloxy group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000008096 xylene Substances 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
Landscapes
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Priority Applications (29)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3404401A DE3404401C2 (de) | 1984-02-08 | 1984-02-08 | Verwendung von Aryloxy-Verbindungen als Antidots |
| EP85100867A EP0154153B1 (de) | 1984-02-08 | 1985-01-29 | Verwendung von Aryloxy-Verbindungen als Antidots |
| AT85100867T ATE55039T1 (de) | 1984-02-08 | 1985-01-29 | Verwendung von aryloxy-verbindungen als antidots. |
| DE8585100867T DE3578923D1 (de) | 1984-02-08 | 1985-01-29 | Verwendung von aryloxy-verbindungen als antidots. |
| AT85100866T ATE40632T1 (de) | 1984-02-08 | 1985-01-29 | Verwendung von chinolyloxy-verbindungen als antidots fuer fenoxapropethyl (ethyl-2(4-(6chlorbenzoxazolyloxy)-phenoxy>-propionat). |
| EP85100866A EP0152006B1 (de) | 1984-02-08 | 1985-01-29 | Verwendung von Chinolyloxy-Verbindungen als Antidots für Fenoxapropethyl (Ethyl-2[4-(6-chlorbenzoxazolyloxy)-phenoxy]-propionat) |
| DE8585100866T DE3568126D1 (en) | 1984-02-08 | 1985-01-29 | Use of quinolinyloxy compounds as antidotes for phenoxaprop ethyl (ethyl-2û4-(6-chlorobenzoxazolyloxy)-phenoxy¨-propionate) |
| HU85394A HU200077B (en) | 1984-02-08 | 1985-02-01 | Antidotum compositions containing aryloxy-compounds as active components and herbicide compositions containing former antidotum |
| HU85414A HU198604B (en) | 1984-02-08 | 1985-02-04 | Compositions comprising quinolyloxy derivatives as antidote and ethyl-2-square brackets open 4-(6-chlorobenzoxazolyloxy)-phenoxy square brackets closed -propionate as herbicide |
| TR5328/85A TR22332A (tr) | 1984-02-08 | 1985-02-05 | Antidot olarak ariloksi ve kinolinoksi bilesiklerinin kullanilmasi |
| US06/698,559 US4602932A (en) | 1984-02-08 | 1985-02-06 | Use of quinolyloxy compounds as antidotes for fenoxaprop-ethyl (ethyl-2-(4-(6-chlorobenzoxazolyloxy)-phenoxy)-propionate) |
| US06/698,553 US4668276A (en) | 1984-02-08 | 1985-02-06 | Use of aryloxy compounds as antidotes |
| AR299443A AR240975A1 (es) | 1984-02-08 | 1985-02-06 | Composicion para tratamiento de plantas |
| AR299444A AR240974A1 (es) | 1984-02-08 | 1985-02-06 | Composiciones para lucha contra malezas herbaceas en cultivos de plantas utiles |
| DK057385A DK166367C (da) | 1984-02-08 | 1985-02-07 | Fremgangsmaade og middel til beskyttelse af kulturplanter mod fytotoksiske bivirkninger af fenoxaprop-ethyl samt anvendelse af midlet |
| AU38538/85A AU575906B2 (en) | 1984-02-08 | 1985-02-07 | Use of aryloxy compounds as antidotes |
| DK57285A DK57285A (da) | 1984-02-08 | 1985-02-07 | Anvendelse af aryloxy-forbindelser som antidoter |
| CA000473734A CA1242092A (en) | 1984-02-08 | 1985-02-07 | Use of quinolyloxy compounds as antidotes for fenoxaprop-ethyl (ethyl-2-[4-(6- chlorobenzoxazolyloxy)-phenoxy]-propionate) |
| ZA85932A ZA85932B (en) | 1984-02-08 | 1985-02-07 | The use of quinolyloxy compounds as antidotes for fenoxapropethyl(ethyl-2-(4(6-chlorobenzoxazolyloxy)-phenoxy)-propionate) |
| JP60021008A JPH0696482B2 (ja) | 1984-02-08 | 1985-02-07 | アリールオキシ化合物を毒性緩和剤として使用する方法 |
| DD85273122A DD231278A5 (de) | 1984-02-08 | 1985-02-07 | Verfahren zum schutz von kulturpflanzen gegen phytotoxische nebenwirkungen von rthyl-2[4-6-chlorzoxazolyloxy)-phenoxy-propionat |
| BR8500548A BR8500548A (pt) | 1984-02-08 | 1985-02-07 | Processo para a protecao de plantas de cultura,emprego e composicao para o combate de ervas daninhas gramineas |
| NZ211065A NZ211065A (en) | 1984-02-08 | 1985-02-07 | The use of quinolyloxy-containing compounds as phytotoxicity antidotes for fenoxaprop-ethyl |
| CA000473735A CA1250151A (en) | 1984-02-08 | 1985-02-07 | Use of aryloxy compounds as antidotes |
| AU38539/85A AU575907B2 (en) | 1984-02-08 | 1985-02-07 | Use of quinolyloxy compounds as antidotes for fernoxaprop- ethyl |
| JP60021009A JPS60188303A (ja) | 1984-02-08 | 1985-02-07 | エチル−２−〔４−（６−クロルベンゾキサゾリルオキシ−フエノキシ〕−プロピオネ−トのための毒性緩和剤としてのキノリルオキシ化合物の使用 |
| BR8500547A BR8500547A (pt) | 1984-02-08 | 1985-02-07 | Enprego de compostos,processo para a protecao de plantas de cultura e composicoes de tratamento de plantas |
| ZA85931A ZA85931B (en) | 1984-02-08 | 1985-02-07 | The use of aryloxy compounds as antidotes |
| DD85273120A DD232418A5 (de) | 1984-02-08 | 1985-02-07 | Verwendung von aryloxy-verbindungen als antidots |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3404401A DE3404401C2 (de) | 1984-02-08 | 1984-02-08 | Verwendung von Aryloxy-Verbindungen als Antidots |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3404401A1 DE3404401A1 (de) | 1985-08-08 |
| DE3404401C2 true DE3404401C2 (de) | 1994-02-10 |
Family
ID=6227111
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3404401A Expired - Lifetime DE3404401C2 (de) | 1984-02-08 | 1984-02-08 | Verwendung von Aryloxy-Verbindungen als Antidots |
| DE8585100867T Expired - Lifetime DE3578923D1 (de) | 1984-02-08 | 1985-01-29 | Verwendung von aryloxy-verbindungen als antidots. |
| DE8585100866T Expired DE3568126D1 (en) | 1984-02-08 | 1985-01-29 | Use of quinolinyloxy compounds as antidotes for phenoxaprop ethyl (ethyl-2û4-(6-chlorobenzoxazolyloxy)-phenoxy¨-propionate) |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8585100867T Expired - Lifetime DE3578923D1 (de) | 1984-02-08 | 1985-01-29 | Verwendung von aryloxy-verbindungen als antidots. |
| DE8585100866T Expired DE3568126D1 (en) | 1984-02-08 | 1985-01-29 | Use of quinolinyloxy compounds as antidotes for phenoxaprop ethyl (ethyl-2û4-(6-chlorobenzoxazolyloxy)-phenoxy¨-propionate) |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US4668276A (en, 2012) |
| EP (2) | EP0152006B1 (en, 2012) |
| JP (2) | JPS60188303A (en, 2012) |
| AR (2) | AR240975A1 (en, 2012) |
| AT (2) | ATE55039T1 (en, 2012) |
| AU (2) | AU575906B2 (en, 2012) |
| BR (2) | BR8500548A (en, 2012) |
| CA (2) | CA1250151A (en, 2012) |
| DD (2) | DD231278A5 (en, 2012) |
| DE (3) | DE3404401C2 (en, 2012) |
| DK (2) | DK166367C (en, 2012) |
| HU (2) | HU200077B (en, 2012) |
| NZ (1) | NZ211065A (en, 2012) |
| TR (1) | TR22332A (en, 2012) |
| ZA (2) | ZA85932B (en, 2012) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3382743D1 (de) * | 1982-05-07 | 1994-05-11 | Ciba Geigy | Verwendung von Chinolinderivaten zum Schützen von Kulturpflanzen. |
| EP0159287B1 (de) * | 1984-03-15 | 1989-10-11 | Ciba-Geigy Ag | Verwendung von Chinolinderivaten zum Schützen von Kulturpflanzen |
| DE3680212D1 (de) * | 1985-02-14 | 1991-08-22 | Ciba Geigy Ag | Verwendung von chinolinderivaten zum schuetzen von kulturpflanzen. |
| DE3624859A1 (de) * | 1986-07-23 | 1988-01-28 | Hoechst Ag | Neue chinolinoxy-verbindungen, verfahren zu ihrer herstellung und ihre verwendung als antidots |
| GB8702613D0 (en) * | 1987-02-05 | 1987-03-11 | Ici Plc | Compositions |
| JPS63249461A (ja) * | 1987-04-02 | 1988-10-17 | Mitsuba Electric Mfg Co Ltd | 磁気結合構造 |
| GB8726735D0 (en) * | 1987-11-14 | 1987-12-16 | Wellcome Found | Pesticidal compounds |
| DE3808896A1 (de) * | 1988-03-17 | 1989-09-28 | Hoechst Ag | Pflanzenschuetzende mittel auf basis von pyrazolcarbonsaeurederivaten |
| US4904295A (en) * | 1988-06-15 | 1990-02-27 | Hoechst Roussel Pharmaceuticals, Inc. | Selective weed control in cereal grain crops |
| US5364832A (en) * | 1990-08-10 | 1994-11-15 | Hoechst Aktiengesellschaft | Water-dispersible granules comprising fenoxaprop-ethyl and/or fenchlorazole |
| US5700758A (en) * | 1989-11-30 | 1997-12-23 | Hoechst Aktiengesellschaft | Pyrazolines for protecting crop plants against herbicides |
| DE3939503A1 (de) * | 1989-11-30 | 1991-06-06 | Hoechst Ag | Neue pyrazoline zum schutz von kulturpflanzen gegenueber herbiziden |
| AU9054291A (en) * | 1990-11-26 | 1992-06-25 | E.I. Du Pont De Nemours And Company | Herbicidal oxazine ethers |
| DE59209849D1 (de) * | 1991-04-15 | 2000-08-24 | Aventis Cropscience Gmbh | Isoxazoline oder Isothiazoline enthaltende pflanzenschützende Mittel, neue Isoxazoline und Isothiazoline und Verfahren zu deren Herstellung |
| DE4217928A1 (de) * | 1992-05-30 | 1993-12-02 | Hoechst Ag | Neue Mischungen aus Herbiziden und Antidots, neue (Hetero-)Aryloxy-Verbindungen, Verfahren zu deren Herstellung, diese enthaltenden Mittel und deren Verwendung |
| TW259690B (en, 2012) | 1992-08-01 | 1995-10-11 | Hoechst Ag | |
| DE19638233A1 (de) * | 1996-09-19 | 1998-03-26 | Hoechst Schering Agrevo Gmbh | Kombinationen aus Sulfonylharnstoff-Herbiziden und Safenern |
| ATE294501T1 (de) | 1998-07-16 | 2005-05-15 | Bayer Cropscience Gmbh | Herbizide mittel |
| GB9922830D0 (en) | 1999-09-27 | 1999-11-24 | Novartis Ag | Processes |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3133810A (en) * | 1961-04-19 | 1964-05-19 | Monsanto Chemicals | Herbicidal compositions |
| US3929452A (en) * | 1971-03-25 | 1975-12-30 | Kumiai Chemical Industry Co | Herbicidal composition |
| DE2546845A1 (de) * | 1975-10-18 | 1977-04-28 | Basf Ag | Substituierte 2-(chinolyl-xy)- und 2-(isochinolyl-oxy)-carbonsaeurederivate |
| US4019892A (en) * | 1975-12-31 | 1977-04-26 | Shell Oil Company | Herbicidal heterocyclic compounds |
| DE2617804C2 (de) * | 1976-04-23 | 1985-01-24 | Hoechst Ag, 6230 Frankfurt | 2-(4-Phenoxy phenoxy)-propionsäurederivate und ihre Verwendung als Herbizide |
| JPS5814354B2 (ja) * | 1976-06-23 | 1983-03-18 | 株式会社小松製作所 | 装軌車両の駆動装置 |
| DE2640730C2 (de) * | 1976-09-10 | 1983-08-25 | Hoechst Ag, 6230 Frankfurt | Benzoxazolyloxy- und Benzothiazolyloxy-phenoxy-Verbindungen und diese enthaltende herbizide Mittel |
| EP0004414B1 (en) * | 1978-03-01 | 1985-07-24 | Imperial Chemical Industries Plc | Mixtures of herbicidal pyridyloxyphenoxypropanoic acid derivatives with other herbicides, and processes of killing unwanted plants therewith |
| DE2914300A1 (de) * | 1979-04-09 | 1980-11-13 | Hoechst Ag | Heterocyclische phenylether und diese enthaltende herbizide mittel |
| DE3000076A1 (de) * | 1980-01-03 | 1981-09-03 | Hoechst Ag, 6000 Frankfurt | Wachstumsfoerdernde und pflanzenschuetzende mittel |
| US4416687A (en) * | 1982-02-01 | 1983-11-22 | Monsanto Company | 3,5-Bis (trifluoromethyl)phenoxy carboxylic acids and derivatives thereof |
| MA19709A1 (fr) * | 1982-02-17 | 1983-10-01 | Ciba Geigy Ag | Application de derives de quinoleine a la protection des plantes cultivees . |
| DE3382743D1 (de) * | 1982-05-07 | 1994-05-11 | Ciba Geigy | Verwendung von Chinolinderivaten zum Schützen von Kulturpflanzen. |
| EP0112799A1 (de) * | 1982-12-06 | 1984-07-04 | Ciba-Geigy Ag | Herbizides Mittel zur selektiven Unkrautbekämpfung in Getreide |
| GB2137092A (en) * | 1983-02-28 | 1984-10-03 | Ici Plc | Phenoxypropionic Acid Derivatives for Selective Herbicides in Rice Crops |
| EP0138773B1 (de) * | 1983-10-18 | 1990-08-29 | Ciba-Geigy Ag | Verwendung von Chinolinderivaten zum Schützen von Kulturpflanzen |
-
1984
- 1984-02-08 DE DE3404401A patent/DE3404401C2/de not_active Expired - Lifetime
-
1985
- 1985-01-29 AT AT85100867T patent/ATE55039T1/de not_active IP Right Cessation
- 1985-01-29 AT AT85100866T patent/ATE40632T1/de not_active IP Right Cessation
- 1985-01-29 DE DE8585100867T patent/DE3578923D1/de not_active Expired - Lifetime
- 1985-01-29 DE DE8585100866T patent/DE3568126D1/de not_active Expired
- 1985-01-29 EP EP85100866A patent/EP0152006B1/de not_active Expired
- 1985-01-29 EP EP85100867A patent/EP0154153B1/de not_active Expired - Lifetime
- 1985-02-01 HU HU85394A patent/HU200077B/hu unknown
- 1985-02-04 HU HU85414A patent/HU198604B/hu unknown
- 1985-02-05 TR TR5328/85A patent/TR22332A/xx unknown
- 1985-02-06 US US06/698,553 patent/US4668276A/en not_active Expired - Lifetime
- 1985-02-06 AR AR299443A patent/AR240975A1/es active
- 1985-02-06 US US06/698,559 patent/US4602932A/en not_active Expired - Lifetime
- 1985-02-06 AR AR299444A patent/AR240974A1/es active
- 1985-02-07 CA CA000473735A patent/CA1250151A/en not_active Expired
- 1985-02-07 NZ NZ211065A patent/NZ211065A/xx unknown
- 1985-02-07 DD DD85273122A patent/DD231278A5/de unknown
- 1985-02-07 ZA ZA85932A patent/ZA85932B/xx unknown
- 1985-02-07 AU AU38538/85A patent/AU575906B2/en not_active Expired
- 1985-02-07 BR BR8500548A patent/BR8500548A/pt unknown
- 1985-02-07 JP JP60021009A patent/JPS60188303A/ja active Granted
- 1985-02-07 BR BR8500547A patent/BR8500547A/pt unknown
- 1985-02-07 JP JP60021008A patent/JPH0696482B2/ja not_active Expired - Lifetime
- 1985-02-07 DK DK057385A patent/DK166367C/da not_active IP Right Cessation
- 1985-02-07 AU AU38539/85A patent/AU575907B2/en not_active Expired
- 1985-02-07 CA CA000473734A patent/CA1242092A/en not_active Expired
- 1985-02-07 DK DK57285A patent/DK57285A/da not_active Application Discontinuation
- 1985-02-07 ZA ZA85931A patent/ZA85931B/xx unknown
- 1985-02-07 DD DD85273120A patent/DD232418A5/de unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE3404401C2 (de) | Verwendung von Aryloxy-Verbindungen als Antidots | |
| DE69625587T2 (de) | Synergistiche herbizide zusammensetzungen mit metolachlor | |
| DD283538A5 (de) | Mittel zum schutz von kulturpflanzen gegen phytotoxische nebenwirkungen von herbiziden | |
| DE3817192A1 (de) | 1,2,4-triazolderivate enthaltende pflanzenschuetzende mittel sowie neue derivate des 1,2,4-triazols | |
| DE3939010A1 (de) | Isoxazoline, verfahren zu ihrer herstellung und ihre verwendung als pflanzenschuetzende mittel | |
| EP0943240B1 (de) | Kombinationen aus Herbiziden und pflanzenschützenden Stoffen | |
| DE69702968T2 (de) | Herbizide zusammensetzung und deren verwendung zur unkrautbekämpfung | |
| EP0003805B1 (de) | Pyridazonverbindungen und diese enthaltende herbizide Zusammensetzungen | |
| DE4026018A1 (de) | Isoxazoline oder isothiazoline enthaltende pflanzenschuetzende mittel und neue isoxazoline und isothiazoline | |
| EP0768034B1 (de) | Herbizides synergistisches Mittel und Verfahren zur Unkrautbekämpfung | |
| EP0596899B1 (de) | Neue mischungen aus herbiziden und antidots | |
| EP1290946B1 (de) | Herbizides Mittel | |
| DE3877826T2 (de) | Herbizide zusammensetzung. | |
| EP0196026B1 (de) | Phosphorhaltige funktionelle Essigsäurederivate, Verfahren zu ihrer Herstellung und sie enthaltende herbizide, wachstumsregulierende Mittel | |
| EP0542687A1 (de) | Synergistisches Mittel und Verfahren zur selektiven Unkrautbekämpfung | |
| EP0112799A1 (de) | Herbizides Mittel zur selektiven Unkrautbekämpfung in Getreide | |
| EP0614608A2 (de) | Synergistische Mischungen zur Bekämpfung von Ackerfuchsschwanz | |
| EP0075249B1 (de) | Herbizide Mittel | |
| DE19506202A1 (de) | Herbizide Mittel enthaltend 3-(2-Chlorphenylmethyl)-1-(1-methyl-1-phenylethyl)- und/oder 1-(1-methyl-1-phenylethyl)-3-(4-tolyl)-harnstoffe sowie mindestens ein 3-Phenyluracil | |
| DE4428982C1 (de) | Neue synergistische Herbizide, insbesondere zur Bekämpfung von Ackerfuchsschwanz | |
| EP0110168A1 (de) | Herbizide Mittel | |
| DE3624859A1 (de) | Neue chinolinoxy-verbindungen, verfahren zu ihrer herstellung und ihre verwendung als antidots | |
| EP0616770A1 (de) | Selektiv-herbizides Mittel | |
| DE4323122A1 (de) | Mischungen aus Herbiziden und Antidots | |
| EP0417626A2 (de) | N-Arylhydrazone enthaltende pflanzenschützende Mittel und neue N-Arylhydrazone |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: HOECHST SCHERING AGREVO GMBH, 13509 BERLIN, DE |
|
| 8327 | Change in the person/name/address of the patent owner |
Owner name: AVENTIS CROPSCIENCE GMBH, 13509 BERLIN, DE |
|
| 8327 | Change in the person/name/address of the patent owner |
Owner name: AVENTIS CROPSCIENCE GMBH, 65929 FRANKFURT, DE |
|
| 8327 | Change in the person/name/address of the patent owner |
Owner name: BAYER CROPSCIENCE GMBH, 65929 FRANKFURT, DE |