CA2435761C - Herbicide-safener combination based on isoxazoline carboxylate safeners - Google Patents
Herbicide-safener combination based on isoxazoline carboxylate safeners Download PDFInfo
- Publication number
- CA2435761C CA2435761C CA2435761A CA2435761A CA2435761C CA 2435761 C CA2435761 C CA 2435761C CA 2435761 A CA2435761 A CA 2435761A CA 2435761 A CA2435761 A CA 2435761A CA 2435761 C CA2435761 C CA 2435761C
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- herbicide
- plants
- alkoxy
- phenyl
- 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
- ZYDBNGULYNHMSF-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole-3-carboxylic acid Chemical compound OC(=O)C1=NOCC1 ZYDBNGULYNHMSF-UHFFFAOYSA-N 0.000 title description 3
- 239000004009 herbicide Substances 0.000 claims abstract description 104
- 230000002363 herbicidal effect Effects 0.000 claims abstract description 82
- 241000196324 Embryophyta Species 0.000 claims abstract description 66
- 150000001875 compounds Chemical class 0.000 claims abstract description 44
- 239000000203 mixture Substances 0.000 claims abstract description 36
- 150000003839 salts Chemical class 0.000 claims abstract description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 14
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
- 239000001257 hydrogen Substances 0.000 claims abstract description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 13
- 239000005504 Dicamba Substances 0.000 claims abstract description 11
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 11
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 10
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 10
- MEFQWPUMEMWTJP-UHFFFAOYSA-N fluroxypyr Chemical compound NC1=C(Cl)C(F)=NC(OCC(O)=O)=C1Cl MEFQWPUMEMWTJP-UHFFFAOYSA-N 0.000 claims abstract description 10
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000005558 Fluroxypyr Substances 0.000 claims abstract description 7
- 239000005627 Triclopyr Substances 0.000 claims abstract description 7
- -1 cyano, nitro, amino Chemical group 0.000 claims description 37
- 150000003254 radicals Chemical class 0.000 claims description 20
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 17
- 238000009472 formulation Methods 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 13
- IRJQWZWMQCVOLA-DNTJNYDQSA-N 2-[(e)-n-[(3,5-difluorophenyl)carbamoylamino]-c-methylcarbonimidoyl]pyridine-3-carboxylic acid Chemical compound N=1C=CC=C(C(O)=O)C=1C(/C)=N/NC(=O)NC1=CC(F)=CC(F)=C1 IRJQWZWMQCVOLA-DNTJNYDQSA-N 0.000 claims description 13
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 11
- 125000003282 alkyl amino group Chemical group 0.000 claims description 11
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 10
- 125000004414 alkyl thio group Chemical group 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
- MWKVXOJATACCCH-UHFFFAOYSA-N isoxadifen-ethyl Chemical compound C1C(C(=O)OCC)=NOC1(C=1C=CC=CC=1)C1=CC=CC=C1 MWKVXOJATACCCH-UHFFFAOYSA-N 0.000 claims description 7
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 6
- ITGSCCPVERXFGN-UHFFFAOYSA-N isoxadifen Chemical compound C1C(C(=O)O)=NOC1(C=1C=CC=CC=1)C1=CC=CC=C1 ITGSCCPVERXFGN-UHFFFAOYSA-N 0.000 claims description 6
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 159000000000 sodium salts Chemical class 0.000 claims description 4
- 231100000674 Phytotoxicity Toxicity 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 2
- 244000045561 useful plants Species 0.000 claims 1
- 240000008042 Zea mays Species 0.000 abstract description 23
- 235000002017 Zea mays subsp mays Nutrition 0.000 abstract description 22
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 abstract description 11
- 235000009973 maize Nutrition 0.000 abstract description 11
- 239000004480 active ingredient Substances 0.000 abstract description 9
- WVQBLGZPHOPPFO-LBPRGKRZSA-N (S)-metolachlor Chemical compound CCC1=CC=CC(C)=C1N([C@@H](C)COC)C(=O)CCl WVQBLGZPHOPPFO-LBPRGKRZSA-N 0.000 abstract description 6
- 239000005617 S-Metolachlor Substances 0.000 abstract description 6
- 125000000217 alkyl group Chemical group 0.000 abstract description 6
- QZXATCCPQKOEIH-UHFFFAOYSA-N Florasulam Chemical compound N=1N2C(OC)=NC=C(F)C2=NC=1S(=O)(=O)NC1=C(F)C=CC=C1F QZXATCCPQKOEIH-UHFFFAOYSA-N 0.000 abstract description 5
- MLKCGVHIFJBRCD-UHFFFAOYSA-N ethyl 2-chloro-3-{2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-4-fluorophenyl}propanoate Chemical group C1=C(Cl)C(CC(Cl)C(=O)OCC)=CC(N2C(N(C(F)F)C(C)=N2)=O)=C1F MLKCGVHIFJBRCD-UHFFFAOYSA-N 0.000 abstract description 5
- IANUJLZYFUDJIH-UHFFFAOYSA-N flufenacet Chemical compound C=1C=C(F)C=CC=1N(C(C)C)C(=O)COC1=NN=C(C(F)(F)F)S1 IANUJLZYFUDJIH-UHFFFAOYSA-N 0.000 abstract description 5
- FOXFZRUHNHCZPX-UHFFFAOYSA-N metribuzin Chemical compound CSC1=NN=C(C(C)(C)C)C(=O)N1N FOXFZRUHNHCZPX-UHFFFAOYSA-N 0.000 abstract description 5
- JLYFCTQDENRSOL-UHFFFAOYSA-N 2-chloro-N-(2,4-dimethylthiophen-3-yl)-N-(1-methoxypropan-2-yl)acetamide Chemical compound COCC(C)N(C(=O)CCl)C=1C(C)=CSC=1C JLYFCTQDENRSOL-UHFFFAOYSA-N 0.000 abstract description 4
- 239000005492 Carfentrazone-ethyl Substances 0.000 abstract description 4
- 239000005529 Florasulam Substances 0.000 abstract description 4
- 239000005531 Flufenacet Substances 0.000 abstract description 4
- 239000005583 Metribuzin Substances 0.000 abstract description 4
- JLYFCTQDENRSOL-VIFPVBQESA-N dimethenamid-P Chemical compound COC[C@H](C)N(C(=O)CCl)C=1C(C)=CSC=1C JLYFCTQDENRSOL-VIFPVBQESA-N 0.000 abstract description 4
- IRJQWZWMQCVOLA-ZBKNUEDVSA-N 2-[(z)-n-[(3,5-difluorophenyl)carbamoylamino]-c-methylcarbonimidoyl]pyridine-3-carboxylic acid Chemical compound N=1C=CC=C(C(O)=O)C=1C(/C)=N\NC(=O)NC1=CC(F)=CC(F)=C1 IRJQWZWMQCVOLA-ZBKNUEDVSA-N 0.000 abstract 1
- 239000005509 Dimethenamid-P Substances 0.000 abstract 1
- YIANBKOBVRMNPR-UHFFFAOYSA-N cloransulam Chemical compound N=1N2C(OCC)=NC(F)=CC2=NC=1S(=O)(=O)NC1=C(Cl)C=CC=C1C(O)=O YIANBKOBVRMNPR-UHFFFAOYSA-N 0.000 abstract 1
- 230000006378 damage Effects 0.000 description 21
- 239000002689 soil Substances 0.000 description 19
- 244000038559 crop plants Species 0.000 description 18
- 239000000575 pesticide Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 240000007594 Oryza sativa Species 0.000 description 12
- 235000007164 Oryza sativa Nutrition 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- 235000009566 rice Nutrition 0.000 description 12
- 208000027418 Wounds and injury Diseases 0.000 description 10
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 10
- 235000005822 corn Nutrition 0.000 description 10
- 208000014674 injury Diseases 0.000 description 10
- 240000005979 Hordeum vulgare Species 0.000 description 9
- 235000007340 Hordeum vulgare Nutrition 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 241000209140 Triticum Species 0.000 description 8
- 235000021307 Triticum Nutrition 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 7
- 235000013339 cereals Nutrition 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 239000004562 water dispersible granule Substances 0.000 description 7
- 239000004495 emulsifiable concentrate Substances 0.000 description 6
- 239000000729 antidote Substances 0.000 description 5
- 239000003995 emulsifying agent Substances 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 238000000227 grinding Methods 0.000 description 5
- 239000002917 insecticide Substances 0.000 description 5
- 235000006008 Brassica napus var napus Nutrition 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 244000299507 Gossypium hirsutum Species 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 229920000151 polyglycol Polymers 0.000 description 4
- 239000010695 polyglycol Substances 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000005995 Aluminium silicate Substances 0.000 description 3
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 3
- 244000068988 Glycine max Species 0.000 description 3
- 235000010469 Glycine max Nutrition 0.000 description 3
- 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 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000021536 Sugar beet Nutrition 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 235000012211 aluminium silicate Nutrition 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 230000012010 growth Effects 0.000 description 3
- 239000003621 irrigation water Substances 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
- 231100001184 nonphytotoxic Toxicity 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 238000009331 sowing Methods 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 230000009261 transgenic effect Effects 0.000 description 3
- 230000000007 visual effect Effects 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical class O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 235000007319 Avena orientalis Nutrition 0.000 description 2
- 244000075850 Avena orientalis Species 0.000 description 2
- 235000014698 Brassica juncea var multisecta Nutrition 0.000 description 2
- 240000002791 Brassica napus Species 0.000 description 2
- 240000000385 Brassica napus var. napus Species 0.000 description 2
- 235000006618 Brassica rapa subsp oleifera Nutrition 0.000 description 2
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 241000209504 Poaceae Species 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- 235000007238 Secale cereale Nutrition 0.000 description 2
- 244000082988 Secale cereale Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 229940100389 Sulfonylurea Drugs 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 2
- DUEPRVBVGDRKAG-UHFFFAOYSA-N carbofuran Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 DUEPRVBVGDRKAG-UHFFFAOYSA-N 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- OWZREIFADZCYQD-NSHGMRRFSA-N deltamethrin Chemical compound CC1(C)[C@@H](C=C(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 OWZREIFADZCYQD-NSHGMRRFSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 238000010410 dusting Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- KVGLBTYUCJYMND-UHFFFAOYSA-N fonofos Chemical compound CCOP(=S)(CC)SC1=CC=CC=C1 KVGLBTYUCJYMND-UHFFFAOYSA-N 0.000 description 2
- 150000002545 isoxazoles Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- BULVZWIRKLYCBC-UHFFFAOYSA-N phorate Chemical compound CCOP(=S)(OCC)SCSCC BULVZWIRKLYCBC-UHFFFAOYSA-N 0.000 description 2
- 230000000885 phytotoxic effect Effects 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 235000012015 potatoes Nutrition 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- XLNZEKHULJKQBA-UHFFFAOYSA-N terbufos Chemical compound CCOP(=S)(OCC)SCSC(C)(C)C XLNZEKHULJKQBA-UHFFFAOYSA-N 0.000 description 2
- YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical class BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- FMPJHEINDXIEHS-UHFFFAOYSA-N (2-phenoxyphenyl) hydrogen carbonate Chemical class OC(=O)OC1=CC=CC=C1OC1=CC=CC=C1 FMPJHEINDXIEHS-UHFFFAOYSA-N 0.000 description 1
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 description 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 1
- ZFHGXWPMULPQSE-SZGBIDFHSA-N (Z)-(1S)-cis-tefluthrin Chemical compound FC1=C(F)C(C)=C(F)C(F)=C1COC(=O)[C@@H]1C(C)(C)[C@@H]1\C=C(/Cl)C(F)(F)F ZFHGXWPMULPQSE-SZGBIDFHSA-N 0.000 description 1
- XBYZOHTXPQOOJM-UHFFFAOYSA-N 1,2-oxazol-3-yl(phenyl)methanone Chemical compound C=1C=CC=CC=1C(=O)C=1C=CON=1 XBYZOHTXPQOOJM-UHFFFAOYSA-N 0.000 description 1
- 125000004776 1-fluoroethyl group Chemical group [H]C([H])([H])C([H])(F)* 0.000 description 1
- XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- DHQGPOIWDYSZML-UHFFFAOYSA-N 2-chloro-n-(2,4-diethylthiophen-3-yl)-n-(1-methoxypropan-2-yl)acetamide Chemical compound CCC1=CSC(CC)=C1N(C(C)COC)C(=O)CCl DHQGPOIWDYSZML-UHFFFAOYSA-N 0.000 description 1
- DHQGPOIWDYSZML-JTQLQIEISA-N 2-chloro-n-(2,4-diethylthiophen-3-yl)-n-[(2s)-1-methoxypropan-2-yl]acetamide Chemical compound CCC1=CSC(CC)=C1N([C@@H](C)COC)C(=O)CCl DHQGPOIWDYSZML-JTQLQIEISA-N 0.000 description 1
- VONWPEXRCLHKRJ-UHFFFAOYSA-N 2-chloro-n-phenylacetamide Chemical class ClCC(=O)NC1=CC=CC=C1 VONWPEXRCLHKRJ-UHFFFAOYSA-N 0.000 description 1
- 125000006022 2-methyl-2-propenyl group Chemical group 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- IIVWHGMLFGNMOW-UHFFFAOYSA-N 2-methylpropane Chemical compound C[C](C)C IIVWHGMLFGNMOW-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- NGBMMSDIZNGAOK-UHFFFAOYSA-N 2h-triazolo[4,5-d]pyrimidine-5-sulfonamide Chemical class NS(=O)(=O)C1=NC=C2NN=NC2=N1 NGBMMSDIZNGAOK-UHFFFAOYSA-N 0.000 description 1
- UPMXNNIRAGDFEH-UHFFFAOYSA-N 3,5-dibromo-4-hydroxybenzonitrile Chemical compound OC1=C(Br)C=C(C#N)C=C1Br UPMXNNIRAGDFEH-UHFFFAOYSA-N 0.000 description 1
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- HRBKVYFZANMGRE-UHFFFAOYSA-N chlorpyrifos-methyl Chemical compound COP(=S)(OC)OC1=NC(Cl)=C(Cl)C=C1Cl HRBKVYFZANMGRE-UHFFFAOYSA-N 0.000 description 1
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- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 229960002483 decamethrin Drugs 0.000 description 1
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- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- OYIKARCXOQLFHF-UHFFFAOYSA-N isoxaflutole Chemical compound CS(=O)(=O)C1=CC(C(F)(F)F)=CC=C1C(=O)C1=C(C2CC2)ON=C1 OYIKARCXOQLFHF-UHFFFAOYSA-N 0.000 description 1
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 229920002113 octoxynol Polymers 0.000 description 1
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- 244000052769 pathogen Species 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
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- 235000020030 perry Nutrition 0.000 description 1
- 239000003090 pesticide formulation Substances 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical class NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical class OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 1
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- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
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- PQTBTIFWAXVEPB-UHFFFAOYSA-N sulcotrione Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O PQTBTIFWAXVEPB-UHFFFAOYSA-N 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
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- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 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
- 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
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01102222.5 | 2001-01-31 | ||
| EP01102222 | 2001-01-31 | ||
| PCT/EP2002/001002 WO2002060255A2 (en) | 2001-01-31 | 2002-01-31 | Herbicide-safener combination based on isoxozoline carboxylate safeners |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2435761A1 CA2435761A1 (en) | 2002-08-08 |
| CA2435761C true CA2435761C (en) | 2011-08-30 |
Family
ID=8176361
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2435761A Expired - Lifetime CA2435761C (en) | 2001-01-31 | 2002-01-31 | Herbicide-safener combination based on isoxazoline carboxylate safeners |
Country Status (17)
| Country | Link |
|---|---|
| US (2) | US20040106518A1 (https=) |
| EP (1) | EP1365649B1 (https=) |
| JP (1) | JP4476547B2 (https=) |
| CN (1) | CN1243474C (https=) |
| AT (1) | ATE357139T1 (https=) |
| AU (1) | AU2002242701B2 (https=) |
| BR (1) | BR0206799B1 (https=) |
| CA (1) | CA2435761C (https=) |
| DE (1) | DE60218986T2 (https=) |
| ES (1) | ES2280508T3 (https=) |
| HU (1) | HUP0303981A3 (https=) |
| MX (1) | MXPA03006879A (https=) |
| PL (2) | PL208071B1 (https=) |
| RU (1) | RU2351132C2 (https=) |
| UA (1) | UA77407C2 (https=) |
| WO (1) | WO2002060255A2 (https=) |
| ZA (1) | ZA200304588B (https=) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE60304862T2 (de) | 2002-06-08 | 2006-11-23 | Bayer Cropscience Gmbh | Kombinationen von herbiziden aromatischen carbonsäuren und safener-mitteln |
| DE102004035137A1 (de) * | 2004-07-20 | 2006-02-16 | Bayer Cropscience Gmbh | Wirkstoffe zur Steigerung der Pathogenabwehr in Pflanzen und Methoden zu ihrer Auffindung |
| CA2591136A1 (en) * | 2004-12-14 | 2006-06-22 | Bayer Cropscience Lp | Methods for increasing maize yields |
| GB0505645D0 (en) * | 2005-03-18 | 2005-04-27 | Syngenta Participations Ag | Herbicidal composition |
| WO2008092615A2 (en) * | 2007-01-29 | 2008-08-07 | Syngenta Participations Ag | Herbicidal composition |
| WO2009089165A2 (en) * | 2008-01-07 | 2009-07-16 | Auburn University | Combinations of herbicides and safeners |
| US20090197765A1 (en) * | 2008-02-05 | 2009-08-06 | Arysta Lifescience North America, Llc | Solid formulation of low melting active compound |
| EP2092825A1 (de) | 2008-02-21 | 2009-08-26 | Bayer CropScience Aktiengesellschaft | Herbizid-Kombinationen enthaltend ein Herbizid der Klasse der Diamino-s-triazine |
| UA109780C2 (uk) * | 2010-01-07 | 2015-10-12 | ДАУ АГРОСАЙЄНСІЗ ЕлЕлСі | ТІАЗОЛО[5,4-d]ПІРИМІДИНИ І ЇХ ЗАСТОСУВАННЯ ЯК АГРОХІМІЧНИХ ЗАСОБІВ |
| EP3216448B8 (en) | 2012-02-06 | 2019-06-05 | Boehringer Ingelheim Animal Health USA Inc. | Parasiticidal oral veterinary compositions comprising systemically-acting active agents, methods and uses thereof |
| WO2013150055A1 (en) | 2012-04-04 | 2013-10-10 | Intervet International B.V. | Solid oral pharmaceutical compositions for isoxazoline compounds |
| HUE032666T2 (en) | 2012-05-24 | 2017-10-30 | Bayer Cropscience Ag | Herbicidal compositions containing N- (tetrazol-5-yl) arylcarboxylic acids |
| UA118765C2 (uk) | 2013-08-09 | 2019-03-11 | Байєр Кропсайєнс Акцієнгезелльшафт | Третинні гербіцидні комбінації, що містять дві сульфонілсечовини |
| EA031197B1 (ru) | 2013-10-25 | 2018-11-30 | Байер Кропсайенс Акциенгезельшафт | Гербицидная композиция, содержащая амиды n-(1,3,4-оксадиазол-2-ил)арилкарбоновых кислот |
| US20190116791A1 (en) * | 2016-03-15 | 2019-04-25 | Fmc Corporation | Use of safeners with ppo inhibitor herbicides |
| CN105941444A (zh) * | 2016-05-20 | 2016-09-21 | 潍坊中农联合化工有限公司 | 氟吡草腙与麦草畏复配除草剂 |
| RU2726431C1 (ru) * | 2019-06-06 | 2020-07-14 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Кубанский государственный аграрный университет имени И.Т. Трубилина" | (4,6-Диметилтриазоло-[1,5-a]пиримидил-2-сульфанил)-2-трифторацетанилид в качестве регулятора роста кукурузы |
| JP7680764B2 (ja) * | 2019-09-27 | 2025-05-21 | ザ ボード オブ トラスティーズ オブ ザ ユニバーシティ オブ アーカンソー | グループ１５除草剤に対するイネの保護 |
| BR102020019868A2 (pt) | 2020-09-28 | 2022-04-12 | Upl Do Brasil Industria E Comercio De Insumos Agropecuarios S.A. | Combinações de herbicidas triazolonas com fitoprotetores |
| BR102020019865A2 (pt) * | 2020-09-28 | 2022-04-12 | Upl Do Brasil Industria E Comercio De Insumos Agropecuarios S.A. | Combinações de herbicidas triazinona com fitoprotetores |
| CN119661462B (zh) * | 2023-09-19 | 2025-10-17 | 郑州手性药物研究院有限公司 | 一种异噁唑类安全剂及其应用 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2149764T3 (es) * | 1991-04-15 | 2000-11-16 | Aventis Cropscience Gmbh | Agentes protectores de plantas que contienen isoxazolinas o isotiazolinas, nuevas isoxazolinas e isotiazolinas y procedimiento para su preparacion. |
| DE4331448A1 (de) * | 1993-09-16 | 1995-03-23 | Hoechst Schering Agrevo Gmbh | Substituierte Isoxazoline, Verfahren zu deren Herstellung, diese enthaltende Mittel und deren Verwendung als Safener |
| DE19638233A1 (de) * | 1996-09-19 | 1998-03-26 | Hoechst Schering Agrevo Gmbh | Kombinationen aus Sulfonylharnstoff-Herbiziden und Safenern |
| US5851963A (en) * | 1997-07-21 | 1998-12-22 | O'bryant; Jeffrey Charles | Organic lubricant |
| EP1104232B8 (de) * | 1998-07-16 | 2010-10-27 | Bayer CropScience AG | Herbizide mittel |
| DE19832017A1 (de) * | 1998-07-16 | 2000-01-27 | Hoechst Schering Agrevo Gmbh | Herbizide Mittel mit substituierten Phenylsulfonylharnstoffen zur Unkrautbekämpfung in Reis |
| BRPI9913641B1 (pt) * | 1998-08-13 | 2015-08-25 | Bayer Cropscience Ag | Combinações herbicidas, processo para combater plantas daninhas, bem como aplicação das referidas combinações |
| DE19853827A1 (de) * | 1998-11-21 | 2000-05-25 | Aventis Cropscience Gmbh | Kombinationen aus Herbiziden und Safenern |
| ES2262540T3 (es) * | 1999-09-08 | 2006-12-01 | Bayer Cropscience Limited | Nuevas composiciones herbicidas. |
| ES2256041T3 (es) * | 1999-09-30 | 2006-07-16 | Bayer Cropscience Ag | Herbicidas selectivos a base de una n-aril-triazolinona. |
| DE19947918A1 (de) * | 1999-10-06 | 2001-04-12 | Bayer Ag | Selektive Herbizide auf Basis von Pyrimidin-Derivaten |
| AU775959B2 (en) * | 1999-11-17 | 2004-08-19 | Bayer Cropscience Ag | Selective herbicides based upon 2,6-disubstituted pyridine derivatives |
| DE19955662B4 (de) * | 1999-11-19 | 2011-03-31 | Arysta LifeScience North America, | Herbizide auf Basis von Carbamoyltriazolinon |
-
2002
- 2002-01-31 DE DE60218986T patent/DE60218986T2/de not_active Expired - Lifetime
- 2002-01-31 HU HU0303981A patent/HUP0303981A3/hu unknown
- 2002-01-31 UA UA2003088107A patent/UA77407C2/uk unknown
- 2002-01-31 AT AT02708323T patent/ATE357139T1/de not_active IP Right Cessation
- 2002-01-31 WO PCT/EP2002/001002 patent/WO2002060255A2/en not_active Ceased
- 2002-01-31 US US10/470,509 patent/US20040106518A1/en not_active Abandoned
- 2002-01-31 CA CA2435761A patent/CA2435761C/en not_active Expired - Lifetime
- 2002-01-31 BR BRPI0206799-4A patent/BR0206799B1/pt active IP Right Grant
- 2002-01-31 CN CN02803476.7A patent/CN1243474C/zh not_active Expired - Lifetime
- 2002-01-31 MX MXPA03006879A patent/MXPA03006879A/es active IP Right Grant
- 2002-01-31 PL PL388370A patent/PL208071B1/pl unknown
- 2002-01-31 AU AU2002242701A patent/AU2002242701B2/en not_active Expired
- 2002-01-31 JP JP2002560461A patent/JP4476547B2/ja not_active Expired - Lifetime
- 2002-01-31 EP EP02708323A patent/EP1365649B1/en not_active Expired - Lifetime
- 2002-01-31 ES ES02708323T patent/ES2280508T3/es not_active Expired - Lifetime
- 2002-01-31 RU RU2003126585/04A patent/RU2351132C2/ru active
- 2002-01-31 PL PL366801A patent/PL207109B1/pl unknown
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2003
- 2003-06-12 ZA ZA200304588A patent/ZA200304588B/en unknown
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2005
- 2005-03-29 US US11/093,658 patent/US7098169B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JP4476547B2 (ja) | 2010-06-09 |
| MXPA03006879A (es) | 2003-11-13 |
| RU2351132C2 (ru) | 2009-04-10 |
| EP1365649A2 (en) | 2003-12-03 |
| HUP0303981A2 (hu) | 2004-03-29 |
| US20050170963A1 (en) | 2005-08-04 |
| ATE357139T1 (de) | 2007-04-15 |
| AU2002242701B2 (en) | 2008-04-03 |
| PL208071B1 (pl) | 2011-03-31 |
| PL207109B1 (pl) | 2010-11-30 |
| CN1243474C (zh) | 2006-03-01 |
| ES2280508T3 (es) | 2007-09-16 |
| BR0206799B1 (pt) | 2013-05-28 |
| WO2002060255A3 (en) | 2003-01-09 |
| DE60218986D1 (de) | 2007-05-03 |
| CA2435761A1 (en) | 2002-08-08 |
| ZA200304588B (en) | 2004-07-19 |
| BR0206799A (pt) | 2004-02-03 |
| UA77407C2 (en) | 2006-12-15 |
| RU2003126585A (ru) | 2005-02-27 |
| CN1484491A (zh) | 2004-03-24 |
| US7098169B2 (en) | 2006-08-29 |
| US20040106518A1 (en) | 2004-06-03 |
| HUP0303981A3 (en) | 2012-10-29 |
| EP1365649B1 (en) | 2007-03-21 |
| WO2002060255A2 (en) | 2002-08-08 |
| DE60218986T2 (de) | 2007-12-13 |
| PL366801A1 (en) | 2005-02-07 |
| JP2004517154A (ja) | 2004-06-10 |
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