DK2691379T3 - Herbicidt og fungicidt aktive 3-phenylisoxazolin-5-carboxamider og 3-phenylisoxazolin-5-thioamider - Google Patents
Herbicidt og fungicidt aktive 3-phenylisoxazolin-5-carboxamider og 3-phenylisoxazolin-5-thioamider Download PDFInfo
- Publication number
- DK2691379T3 DK2691379T3 DK12713928.5T DK12713928T DK2691379T3 DK 2691379 T3 DK2691379 T3 DK 2691379T3 DK 12713928 T DK12713928 T DK 12713928T DK 2691379 T3 DK2691379 T3 DK 2691379T3
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- Prior art keywords
- cyano
- group
- substituted
- radicals
- alkoxy
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 199
- 239000000460 chlorine Chemical group 0.000 claims description 199
- 229910052801 chlorine Inorganic materials 0.000 claims description 199
- 229910052731 fluorine Inorganic materials 0.000 claims description 199
- 239000011737 fluorine Chemical group 0.000 claims description 199
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 166
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 166
- 229910052794 bromium Inorganic materials 0.000 claims description 166
- -1 chloro, bromo, iodo Chemical group 0.000 claims description 164
- 125000001153 fluoro group Chemical group F* 0.000 claims description 129
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 127
- 239000001257 hydrogen Substances 0.000 claims description 127
- 229910052739 hydrogen Inorganic materials 0.000 claims description 127
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 117
- 150000001875 compounds Chemical class 0.000 claims description 108
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- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 52
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- VPYZWWRTQYPRGL-UHFFFAOYSA-N 3-phenyl-4,5-dihydro-1,2-oxazole-5-carboxamide Chemical class O1C(C(=O)N)CC(C=2C=CC=CC=2)=N1 VPYZWWRTQYPRGL-UHFFFAOYSA-N 0.000 claims description 21
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- RTWIRLHWLMNVCC-WQYNNSOESA-M sodium (2S)-2-[[(2S)-2-[[(2S)-2-amino-4-[hydroxy(methyl)phosphoryl]butanoyl]amino]propanoyl]amino]propanoate Chemical compound [Na+].[O-]C(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@@H](N)CCP(C)(O)=O RTWIRLHWLMNVCC-WQYNNSOESA-M 0.000 description 1
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- JKPSVOHVUGMYGH-UHFFFAOYSA-M sodium;(4,6-dimethoxypyrimidin-2-yl)-[[3-methoxycarbonyl-6-(trifluoromethyl)pyridin-2-yl]sulfonylcarbamoyl]azanide Chemical compound [Na+].COC(=O)C1=CC=C(C(F)(F)F)N=C1S(=O)(=O)NC(=O)[N-]C1=NC(OC)=CC(OC)=N1 JKPSVOHVUGMYGH-UHFFFAOYSA-M 0.000 description 1
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Classifications
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- 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
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
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- 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
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- 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
- A01N43/82—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 three ring hetero atoms
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/04—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
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Claims (13)
1. 3-Phenylisoxazolin-5-carboxamider eller 3- phenvlisoxazolin-5-thioamider med formel (I) eller salte deraf
hvori R1 og R2 uafhængigt af hinanden hver er hydrogen, fluor, chlor, brom, iod, cyano, eller (C1-C4)-alkyl eller (Ci-Ci)-alkoxy substitueret med i hvert tilfælde m radikaler fra gruppen, der består af fluor, chlor, brom, iod og cyano, eller R1 og R2 sammen med carbonatomet, hvortil de er bundet, danner en mættet, delvist eller helt umættet 3-, 4- eller 5-leddet ring, der består af q carbonatomer og p oxygenatomer; R3 er fluor, chlor, cyano, (C1-C3)-alkylcarbonyloxy eller S(0)nR5, eller (Ci-Ce) -alkyl, (C3-C6) -cycloalkyl, (C2-C6) -alkenyl eller (C2-C6) -alkynyl substitueret med i hvert tilfælde m radikaler fra gruppen, der består af fluor, chlor, brom, iod, cyano, (Ci — C4)-alkoxy og hydroxy, eller (C1-C6) -alkylcarbonyl, (C2-C6)-alkenylcarbonyl eller (C3- Ce)-cycloalkylcarbonyl substitueret med i hvert tilfælde m radikaler fra gruppen, der består af fluor, chlor, brom, iod, cyano og (C1-C6) -alkoxy; R4 er hydrogen, cyano, eller (Ci-Cs) -alkyl eller (C3-C8) -cycloalkyl substitueret med i hvert tilfælde m radikaler fra gruppen, der består af fluor, chlor, brom, iod, cyano, hydroxy og (C1-C6) -alkoxy; A er en binding eller en divalent enhed fra gruppen, der består af
R10, R11, R12, R13, R14 og R15 hver uafhængigt af hinanden er hydrogen, fluor, chlor, brom, iod, hydroxy, cyano, CO2R8, CONR6R8, R5, eller (C1-C6)-alkyl, (C3-C5) -cycloalkyl, (C2-C6) -alkenyl, (C2- Ce)-alkynyl, som hver er substitueret med m radikaler fra gruppen, der består af fluor, chlor, brom, rod, hydroxy og cyano; eller (C1-C6) -alkoxy, (C3-C6) -cycloalkoxy, (C2-C6)-alkenyloxy eller (C2-C6) -alkynyloxy, som hver er substitueret med m radikaler fra gruppen, der består af fluor, chlor, brom, iod, cyano og (C1-C2) -alkoxy, Y er oxygen eller svovl; X er hydrogen, cyano, hydroxy, X1, eller (C1-C12) -alkyl, (C3-C8) -cycloalkyl, (C2-C12) -alkenyl eller (C2-C12)-alkynyl substitueret i hvert tilfælde med m radikaler fra gruppen, der består af fluor, chlor, brom, iod, cyano, hydroxy, OR7, X1, OX1, NHX1, S(0)nR5, S02NR6R7, S02NR6R8, C02R8, CONR6R8, COR6, C0NR8S02R5, NR6R8, NR6COR8, NR6CONR8R8, NR6C02R8, NRsS02R8, NRsS02NR6R8, OCONRSR8, OCSNRSR8, POR9R9 og C(R6)=NOR8, eller X, A og R4 sammen med nitrogenatomet, hvortil de er bundet, danner en mættet, delvist eller helt umættet 5-, 6- eller 7- leddet ring, der foruden dette nitrogenatom indeholder k carbonatomer, n oxygenatomer, p svovlatomer og p elementer fra gruppen, der består af NR7 og NCOR7, som ringatomer, hvor et carbonatom bærer p oxogrupper; XI er en 5- eller 6-leddet mættet, delvist umættet, helt umættet eller aromatisk ring, der består af r carbonatomer, s nitrogenatomer, n svovlatomer og n oxygenatomer og substitueret med n radikaler fra gruppen, der består af R6, R6a, R8 og R9; X2, X4 og X6 uafhængigt af hinanden hver er hydrogen, fluor, chlor, brom, iod, cyano, nitro, eller (C1-C4)-alkyl, (C3-C5) -cycloalkyl, (C2-C4) -alkenyl, (C2- C4)-alkynyl, (C1-C4)-alkoxy, (C2-C4)-alkenyloxy, (C2-C4) - alkynyloxy eller (C1-C4) -alkylcarbonyl, der hver er substitueret med m radikaler fra gruppen, der består af fluor, chlor, brom, iod, cyano og (C1-C4)-alkoxy; X3 er fluor, chlor, brom, iod, hydroxy, cyano, nitro, SF5, C0NR8S02R5, CONR6R8, COR6, CO2R8, CONR6R8, C(R6)=NOR8, NR6COR8, NR6CONR8R8, NR6C02R8, NR6S02R8, NR6S02NR6R8, OCONRsR8, OSO2R5, R5, S(0)nR5, so2nrsr8, oso2nr6r8, eller (C1-C6)-alkyl, (C3-C5) -cycloalkyl, (C2-C6) -alkenyl, (C2- Ce)-alkynyl, der hver er substitueret med m radikaler fra gruppen, der består af fluor, chlor, brom, iod, hydroxy og cyano, eller (C1-C6) -alkoxy, (C3-C6) -cycloalkoxy, (C2-C6)-alkenyloxy eller (C2-C6) -alkynyloxy, der hver er substitueret med m radikaler fra gruppen, der består af fluor, chlor, brom, iod, cyano og (C1-C2) -alkoxy, X5 er hydrogen eller X3; R5 er (C1-C6) -alkyl eller (C2-Cg)-cycloalkyl, der hver er substitueret med m radikaler fra gruppen, der består af fluor, chlor, brom, iod, cyano og hydroxy; R5 er hydrogen eller R5; R6a er fluor, chlor, brom, iod, cyano, hydroxy, S(0)nR5 eller (C1-C6) -alkoxy, (C2-Cg) -alkenyloxy eller (C3-C5) -alkynyloxy, der hver er substitueret med m radikaler fra gruppen, der består af fluor, chlor, brom, cyano og (C1-C2)-alkoxy; R7 er hydrogen eller (C1-C6)-alkyl, (Cs-Cg) -cycloalkyl, (C2-C4)- alkenyl eller (C2-C4) -alkynyl, der hver er substitueret med m radikaler fra gruppen, der består af fluor, chlor, brom, cyano og (C1-C2) -alkoxy; r8 er p7. R9 er (C1-C3) -alkyl eller (C1-C3) -alkoxy; k er 3, 4, 5 eller 6; m er 0, 1, 2, 3, 4 eller 5; n er 0, 1 eller 2; p er 0 eller 1; q er 3, 4 eller 5; r er 1, 2, 3, 4 eller 5; s er 0, 1, 2, 3 eller 4; med det forbehold at X3 og X4 ikke begge er substitueret eller usubstitueret alkoxy. 2. 3-Phenylisoxazolin-5-carboxamider eller 3- phenylisoxazolin-5-thioamider med formel (I) eller salte deraf
hvori R1 og R2 uafhængigt af hinanden hver er hydrogen, fluor, chlor, brom, rod, cyano, eller (C1-C4)-alkyl eller (Ci-Ci)-alkoxy substitueret med i hvert tilfælde m radikaler fra gruppen, der består af fluor, chlor, brom, lod og cyano, eller R1 og R2 sammen med carbonatomet, hvortil de er bundet, danner en mættet, delvist eller helt umættet 3-, 4- eller 5-leddet ring, der består af q carbonatomer og p oxygenatomer; R3 er fluor, chlor, cyano, (C1-C3)-alkylcarbonyloxy eller S(0)nR5, eller (Ci-Ce) -alkyl, (C3-C6) -cycloalkyl, (C2-C6) -alkenyl eller (C2-C6) -alkynyl substitueret med i hvert tilfælde m radikaler fra gruppen, der består af fluor, chlor, brom, rod, cyano, (Ci — C4)-alkoxy og hydroxy, eller (C1-C6) -alkylcarbonyl, (C2-C6)-alkenylcarbonyl eller (C3- Ce)-cycloalkylcarbonyl substitueret med i hvert tilfælde m radikaler fra gruppen, der består af fluor, chlor, brom, rod, cyano og (C1-C6) -alkoxy; R4 er hydrogen, cyano, eller (Ci-Cs) -alkyl eller (C3-C8) -cycloalkyl substitueret med i hvert tilfælde m radikaler fra gruppen, der består af fluor, chlor, brom, iod, cyano, hydroxy og (C1-C6) -alkoxy; A er en binding eller en divalent enhed fra gruppen, der hpstår pif
R10, R11, R12, R13, R14 og R15 hver uafhængigt af hinanden er hydrogen, fluor, chlor, brom, iod, hydroxy, cyano, CO2R8, CONR6R8, R5, eller (Ci-Cs)-alkyl, (C3-C5) -cycloalkyl, (C2-C6) -alkenyl, (C2- Cb)-alkynyl, der hver er substitueret med m radikaler fra gruppen, der består af fluor, chlor, brom, iod, hydroxy og cyano; eller (C1-C6) -alkoxy, (C3-C6) -cycloalkoxy, (C'z~Cb)-alkenyloxy eller (C2-C6) -alkynyloxy, der hver er substitueret med m radikaler fra gruppen, der består af fluor, chlor, brom, iod, cyano og (C1-C2) -alkoxy, Y er oxygen eller svovl; X er hydrogen, cyano, hydroxy, X1, eller (C1-C12) -alkyl, (C3-C8) -cycloalkyl, (C2-C12) -alkenyl eller (C2 — C12) -alkynyl substitueret med i hvert tilfælde m radikaler fra gruppen, der består af fluor, chlor, brom, iod, cyano, hydroxy, OR7, X1, OX1, NHX1, S(0)nRb, S02NR6R7, S02NR6R8, C02R8, CONR6R8, COR6, C0NR8S02R5, NR6R8, NR6COR8, NR6CONR8R8, nr6co2r8, NRsS02R8, NRsS02NR6R8, OCONR6R8, OCSNRSR8, POR9R9 og C(R6)=NOR8, eller X, A og R4 sammen med nitrogenatomet, hvortil de er bundet, danner en mættet, delvist eller helt umættet 5-, 6- eller 7- leddet ring, der foruden dette nitrogenatom indeholder k carbonatomer, n oxygenatomer, p svovlatomer og p elementer fra gruppen, der består af NR7 og NCOR7, som ringatomer, hvor et carbonatom bærer p oxogrupper; XI er en ring substitueret med n radikaler fra gruppen, der består af R6, R6a, R8 og
R9, fra gruppen, der består af
X2, X4 og Xs uafhængigt af hinanden hver er hydrogen, fluor, chlor, brom, iod, cyano, nitro, eller (Ci-Ch)-alkyl, (C3-C5) -cycloalkyl, (C2-C4) -alkenyl, (C2- C4)-alkynyl, (C1-C4)-alkoxy, (C2-C4)-alkenyloxy, (C2-C4)-alkynyloxy eller (C1-C4) -alkylcarbonyl, som hver er substitueret med m radikaler fra gruppen, der består af fluor, chlor, brom, iod, cyano og (C1-C4)-alkoxy; X3 er fluor, chlor, brom, rod, hydroxy, cyano, nitro, SFs, C0NR8S02R5, CONR6R8, COR6, CO2R8, CONR6R8, C(R6)=NOR8, NR6COR8, NR6CONR8R8, NR6C02R8, NR6S02R8, NR6S02NR6R8, OCONR6R8, 0S02R5, R5, S(0)nR5, S02NRsR8, 0S02NR6R8, eller (C1-C6)-alkyl, (C3-C5) -cycloalkyl, (C2-C6) -alkenyl, (C2- Cb)-alkynyl, der hver er substitueret med m radikaler fra gruppen, der består af fluor, chlor, brom, rod, hydroxy og cyano, eller (C1-C6)-alkoxy, (Cs-Ce) -cycloalkoxy, (C2-C6)-alkenyloxy eller (C2-C6) -alkynyloxy, der hver er substitueret med m radikaler fra gruppen, der består af fluor, chlor, brom, iod, cyano og (Ci-C2) -alkoxy, X5 er hydrogen eller X3; R5 er (Ci-Ce)-alkyl eller (Cs-Cg)-cycloalkyl, der hver er substitueret med m radikaler fra gruppen, der består af fluor, chlor, brom, iod, cyano og hydroxy; R5 er hydrogen eller R5; R6a er fluor, chlor, brom, iod, cyano, hydroxy, S(0)nR5 eller (C1-C6) -alkoxy, (C2-C6) -alkenyloxy eller (C2-Cs) -alkynyloxy, der hver er substitueret med m radikaler fra gruppen, der består af fluor, chlor, brom, cyano og (C1-C2)-alkoxy; R7 er hydrogen eller (C1-C6)-alkyl, (C3-Cg) -cycloalkyl, (C2-C4)- alkenyl eller (C2-C4) -alkynyl, der hver er substitueret med m radikaler fra gruppen, der består af fluor, chlor, brom, cyano og (C1-C2) -alkoxy; R8 er R7; R9 er (C1-C3) -alkyl eller (C1-C3) -alkoxy; k er 3, 4, 5 eller 6; m er 0, 1, 2, 3, 4 eller 5; n er 0, 1 eller 2; p er 0 eller 1; q er 3, 4 eller 5; med det forbehold at X3 og X4 ikke begge er substitueret eller usubstitueret alkoxy. 3. 3-Phenylisoxazolin-5-carboxamider eller 3- phenylisoxazolin-5-thioamider ifølge krav 1 eller 2, hvori R1 og R2 uafhængigt af hinanden hver er hydrogen, fluor, chlor, brom, iod, cyano eller (C1-C4)-alkyl substitueret med i hvert tilfælde m radikaler fra gruppen, der består af fluor, chlor, brom, iod og cyano, R3 er fluor, chlor eller cyano, eller (C1-C6)-alkyl, (C3-C6) -cycloalkyl, (C2-C6)-alkenyl, (C2- Ce)-alkynyl, der hver er substitueret med m radikaler fra gruppen, der består af fluor og chlor, eller (Ci-Ce)-alkylcarbonyl, der er substitueret med m radikaler fra gruppen, der består af fluor og chlor; A er en binding eller en divalent enhed fra gruppen, der består af CH2, CH2CH2, CHCH3, CH2CH2CH2, CH (CH2CH3) , CH(CH3)CH2, C(CH3)2, C(CH3)2CH2, C (iPr) CH3, CH (CH2iPr) CH2, CH2CH=CH, C(CH3)2C=C, CH(CF3)CH2, CH(CH3)CH20, ch2ch2o, CH (cPr) CH20, CH(CH2OCH3), CH (CH2CH2SCH3) , CH(COOH), CH(COOCH3), CH(COOH)CH2, CH (COOCH3) CH2, CH2COH(CF3), CH(CONHCH3), CH (CONHCHs) CH2 og CH2CH2CONHCH2; R4 er hydrogen eller (Ci-Cs) -alkyl; Y er oxygen eller svovl; X er hydrogen, cyano, hydroxy, X1, eller (C1-C12) -alkyl, (C3-C8) -cycloalkyl, (C2-C12) -alkenyl eller (C2-C12) -alkynyl, der hver er substitueret med m radikaler fra gruppen, der består af fluor, chlor, cyano, hydroxy, OR7, X1, OX1, NHX1, S(0)nR5, CO2R3, CONR6R8, C0NR8S02R5 og POR9R9; X1 er en ring substitueret med n radikaler fra gruppen, der består af R6, R6a, R8 og R9, fra gruppen, der består af
X2, X4 og Xs uafhængigt af hinanden hver er hydrogen, fluor eller chlor, eller (C1-C4) -alkyl eller (C1-C4)-alkoxy, der hver er substitueret med m radikaler fra gruppen, der består af fluor, chlor, cyano og (C1-C4)-alkoxy; X3 er fluor, chlor, brom, cyano, eller (Οι-Οε) -alkyl, der i hvert tilfælde er substitueret med m radikaler fra gruppen, der består af fluor og chlor; eller (C1-C6) -alkoxy, der er substitueret med m radikaler fra gruppen, der består af fluor og chlor; X5 er hydrogen eller X3; R5 er methyl eller ethyl; R5 er hydrogen eller R5; RGa er fluor, chlor, brom, iod, cyano, hydroxy, S(0)nR5 eller (C1-C6)-alkoxy, (C2-C6) -alkenyloxy eller (C2-C6)-alkynyloxy, der hver er substitueret med m radikaler fra gruppen, der består af fluor, chlor, brom, cyano og (C1-C2)-alkoxy; R7 er hydrogen eller (C1-C6) -alkyl, der er substitueret med i hvert tilfælde m radikaler fra gruppen, der består af fluor og chlor; R8 er R7; R1 er (C1-C3) -alkoxy; m er 0, 1, 2 eller 3; n er 0, 1 eller 2; med det forbehold at X3 og X4 ikke begge er substitueret eller usubstitueret alkoxy.
4. Herbicid sammensætning, der omfatter en herbicidt effektiv mængde af mindst én forbindelse med formel (I) ifølge et hvilket som helst af kravene 1 til 3.
5. Herbicid sammensætning ifølge krav 4 i en blanding med formuleringshjælpestoffer.
6. Herbicid sammensætning ifølge krav 4 eller 5, der omfatter mindst én yderligere pesticidt aktiv forbindelse fra gruppen, der består af insekticider, acaricider, herbicider, fungicider, safenere og vækstregulatorer.
7. Herbicid sammensætning ifølge krav 6, der omfatter en safener.
8. Herbicid sammensætning ifølge krav 7, hvor safeneren er udvalgt fra gruppen, der består af mefenpyr-diethyl, cyprosulfamid, isoxadifen-ethyl, cloquintocet-mexyl, benoxacor og dichlormid. 1 Herbicid sammensætning ifølge et hvilket som helst af kravene 6 til 8, der omfatter et yderligere herbicid.
10. Anvendelse af 3-phenylisoxazolin-5-carboxamider eller 3-phenylisoxazolin-5-thioamider med formel (la)
hvori R1 og R2 uafhængigt af hinanden hver er hydrogen, fluor, chlor, brom, iod, cyano, eller (C1-C4)-alkyl eller (CI-C4)-alkoxy substitueret med i hvert tilfælde m radikaler fra gruppen, der består af fluor, chlor, brom, iod og cyano, eller R1 og R2 sammen med carbonatomet, hvortil de er bundet, danner en mættet, delvist eller helt umættet 3-, 4- eller 5-leddet ring, der består af q carbonatomer og p oxygenatomer; R3 er fluor, chlor, cyano, (C1-C3)-alkylcarbonyloxy eller S(O)nR5, eller (Ci-Ce) -alkyl, (C3-C6) -cycloalkyl, (C2-C6) -alkenyl eller (C2-C6) -alkynyl substitueret med i hvert tilfælde m radikaler fra gruppen, der består af fluor, chlor, brom, iod, cyano, (Ci — C4)-alkoxy og hydroxy, eller (C1-C6) -alkylcarbonyl, (C2-C6)-alkenylcarbonyl eller (C3- Ce) -cycloalkylcarbonyl substitueret med i hvert tilfælde m radikaler fra gruppen, der består af fluor, chlor, brom, iod, cyano og (C1-C6) -alkoxy; R4 er hydrogen, cyano, hydroxy, eller (Ci-Cs) -alkyl eller (C3-C8) -cycloalkyl substitueret med i hvert tilfælde m radikaler fra gruppen, der består af fluor, chlor, brom, iod, cyano, hydroxy og (C1-C6) -alkoxy; A er en binding eller en divalent enhed fra gruppen, der består af
R10, R11, R12, R13, R14 og R15 hver uafhængigt af hinanden er hydrogen, fluor, chlor, brom, iod, hydroxy, cyano, CO2R8, CONR6R8, R5, eller (Ci-Cs)-alkyl, (C3-C5) -cycloalkyl, (C2-C6) -alkenyl, (C2- Cb)-alkynyl, der hver er substitueret med m radikaler fra gruppen, der består af fluor, chlor, brom, iod, hydroxy og cyano; eller (C1-C6) -alkoxy, (C3-C6) -cycloalkoxy, (C'z~Cb)-alkenyloxy eller (C2-C6) -alkynyloxy, der hver er substitueret med m radikaler fra gruppen, der består af fluor, chlor, brom, iod, cyano og (C1-C2) -alkoxy, Y er oxygen eller svovl; X er hydrogen, cyano, hydroxy, X1, eller (C1-C12) -alkyl, (C3-C8) -cycloalkyl, (C2-C12) -alkenyl eller (C2 — C12) -alkynyl substitueret med i hvert tilfælde m radikaler fra gruppen, der består af fluor, chlor, brom, iod, cyano, hydroxy, OR7, X1, OX1, NHX1, S(0)nRb, S02NR6R7, S02NR6R8, C02R8, CONR6R8, COR6, C0NR8S02R5, NR6R8, NR6COR8, NR6CONR8R8, nr6co2r8, NRsS02R8, NRsS02NR6R8, OCONR6R8, OCSNRSR8, POR9R9 og C(R6)=NOR8, eller X, A og R4 sammen med nitrogenatomet, hvortil de er bundet, danner en mættet, delvist eller helt umættet 5-, 6- eller 7- leddet ring, der foruden dette nitrogenatom indeholder k carbonatomer, n oxygenatomer, p svovlatomer og p elementer fra gruppen, der består af NR7 og NCOR7, som ringatomer, hvor et carbonatom bærer p oxogrupper; XI er en 5- eller 6-leddet mættet, delvist umættet, helt umættet eller aromatisk ring, der består af r carbonatomer, s nitrogenatomer, n svovlatomer og n oxygenatomer og er substitueret med n radikaler fra gruppen, der består af R6, R5a, R8 og R9; eller phenyl, der er substitueret med n radikaler fra gruppen, der består af R6, R8 og R9; X2, X4 og X6 uafhængigt af hinanden hver er hydrogen, fluor, chlor, brom, iod, cyano, nitro, eller (C1-C4)-alkyl, (C3-C5) -cycloalkyl, (C2-C4) -alkenyl, (C2 — C4)-alkynyl, (C1-C4)-alkoxy, (C2-C4)-alkenyloxy, (C2-C4)-alkynyloxy eller (C1-C4) -alkylcarbonyl, der hver er substitueret med m radikaler fra gruppen, der består af fluor, chlor, brom, iod, cyano og (C1-C4)-alkoxy; X3 er hydrogen, fluor, chlor, brom, iod, hydroxy, cyano, nitro, SFs, C0NR8S02R5, CONR6R8, COR6, CO2R8, CONR6R8, C(R6)=NOR8, NR6COR8, NR6CONR8R8, NR6C02R8, NR6S02R8, NR6S02NR6R8, OCONR6R8, 0S02R5, R5, S(0)nR5, S02NR6R8, oso2nr6r8, eller (C1-C6)-alkyl, (C3-C5) -cycloalkyl, (C2-C6) -alkenyl, (C2- Cb)-alkynyl, der hver er substitueret med m radikaler fra gruppen, der består af fluor, chlor, brom, iod, hydroxy og cyano, eller (C1-C6) -alkoxy, (C3-C6) -cycloalkoxy, (C2-C6)-alkenyloxy eller (C2-C6) -alkynyloxy, der hver er substitueret med m radikaler fra gruppen, der består af fluor, chlor, brom, iod, cyano og (Ci-C2) -alkoxy, X5 er hydrogen eller X3; R5 er (C1-C6)-alkyl eller (Cs-Cg)-cycloalkyl, der hver er substitueret med m radikaler fra gruppen, der består af fluor, chlor, brom, iod, cyano og hydroxy; R5 er hydrogen eller R5; R5a er fluor, chlor, brom, iod, cyano, hydroxy, S(0)nR5 eller (C1-C6) -alkoxy, (C2-C6) -alkenyloxy eller (C2-Cs) -alkynyloxy, der hver er substitueret med m radikaler fra gruppen, der består af fluor, chlor, brom, cyano og (Ci-C2)-alkoxy; R7 er hydrogen eller (C1-C6)-alkyl, (C2-Ce) -cycloalkyl, (C2-C4)- alkenyl eller (C2-C4) -alkynyl, der hver er substitueret med m radikaler fra gruppen, der består af fluor, chlor, brom, cyano og (C1-C2) -alkoxy; r8 er R7. R9 er (Ci-C3)-alkyl eller (C i-C3) -alkoxy; k er 3, 4, 5 eller 6; m er 0, 1, 2, 3, 4 eller 5; n er 0, 1 eller 2; p er 0 eller 1; q er 3, 4 eller 5; r er 1, 2, 3, 4 eller 5; s er O, 1, 2, 3 eller 4; til bekæmpelse af uønskede planter.
11. Anvendelse af 3-phenylisoxazolin-5-carboxamider eller 3-phenylisoxazolin-5-thioamider med formel (la)
hvori R1 og R2 uafhængigt af hinanden hver er hydrogen, fluor, chlor, brom, iod, cyano, eller (C1-C9)-alkyl eller (C:-C4)-alkoxy substitueret med i hvert tilfælde m radikaler fra gruppen, der består af fluor, chlor, brom, iod og cyano, eller R1 og R2 sammen med carbonatomet, hvortil de er bundet, danner en mættet, delvist eller helt umættet 3-, 4- eller 5-leddet ring, der består af q carbonatomer og p oxygenatomer; R3 er fluor, chlor, cyano, (C1-C3)-alkylcarbonyloxy eller S(0)nR5, eller (Ci-Ce) -alkyl, (C3-C6) -cycloalkyl, (C2-C6) -alkenyl eller (C2-C6) -alkynyl substitueret med i hvert tilfælde m radikaler fra gruppen, der består af fluor, chlor, brom, iod, cyano, (Ci-C4)-alkoxy og hydroxy, eller (C1-C6) -alkylcarbonyl, (C2-C6)-alkenylcarbonyl eller (C3- Cg)-cycloalkylcarbonyl substitueret med i hvert tilfælde m radikaler fra gruppen, der består af fluor, chlor, brom, iod, cyano og (C1-C6) -alkoxy; R4 er hydrogen, cyano, hydroxy, eller (Ci-Cs) -alkyl eller (C3-C8) -cycloalkyl substitueret med i hvert tilfælde m radikaler fra gruppen, der består af fluor, chlor, brom, iod, cyano, hydroxy og (Ci-Ce) -alkoxy; A er en binding eller en divalent enhed fra gruppen, der består af
R10, R11, R12, R13, R14 og R15 hver uafhængigt af hinanden er hydrogen, fluor, chlor, brom, iod, hydroxy, cyano, CO2R8, CONR6R8, R5, eller (C1-C6)-alkyl, (C3-C5) -cycloalkyl, (C2-C6) -alkenyl, (C2 — Cb)-alkynyl, der hver er substitueret med m radikaler fra gruppen, der består af fluor, chlor, brom, iod, hydroxy og cyano; eller (C1-C6) -alkoxy, (C3-C6) -cycloalkoxy, (C2-C6)-alkenyloxy eller (02-0ε) -alkynyloxy, der hver er substitueret med m radikaler fra gruppen, der består af fluor, chlor, brom, iod, cyano og (C1-C2) -alkoxy, Y er oxygen eller svovl; X er hydrogen, cyano, hydroxy, X1, eller (C1-C12) -alkyl, (C3-C8) -cycloalkyl, (C2-C12) -alkenyl eller (C2-C12)-alkynyl substitueret med i hvert tilfælde m radikaler fra gruppen, der består af fluor, chlor, brom, iod, cyano, hydroxy, X1, OX1, NHX1, S(0)nR5, S02NR6R7, S02NR6R8, C02R8, CONR6R8, COR6, C0NR8S02R5, NR6R8, NR6COR8, NR6CONR8R8, nr6co2r8, NRsS02R8, NRsS02NR6R8, OCONRSR8, OCSNRSR8, POR9R9 og C(R6)=NOR8, eller X, A og R4 sammen med nitrogenatomet, hvortil de er bundet, danner en mættet, delvist eller helt umættet 5-, 6- eller 7- leddet ring, der foruden dette nitrogenatom indeholder k carbonatomer, n oxygenatomer, p svovlatomer og p elementer fra gruppen, der består af NR7 og NCOR7, som ringatomer, hvor et carbonatom bærer p oxogrupper; XI er en ring substitueret med n radikaler fra gruppen, der består af R6, R6a, R8 og R9, fra gruppen, der består af
eller phenyl, der er substitueret med n radikaler fra gruppen, der består af R6, R8 og R9; X2, X4 og X6 uafhængigt af hinanden hver er hydrogen, fluor, chlor, brom, iod, cyano, nitro, eller (C1-C4)-alkyl, (C3-C5) -cycloalkyl, (C2-C4) -alkenyl, (C2- C4)-alkynyl, (C1-C4)-alkoxy, (C2-C4)-alkenyloxy, (C2-C4)-alkynyloxy eller (C1-C4) -alkylcarbonyl, der hver er substitueret med m radikaler fra gruppen, der består af fluor, chlor, brom, iod, cyano og (C1-C4)-alkoxy; X3 er hydrogen, fluor, chlor, brom, iod, hydroxy, cyano, nitro, SFb, C0NR8S02R5, CONR6R8, COR6, CO2R8, CONR6R8, C(R6)=NOR8, NR6COR8, NR6CONR8R8, NR6C02R8, NR6S02R8, NR6S02NR6R8, OCONR6R8, 0S02R5, R5, S(0)nR5, S02NR6R8, 0S02NR6R8, eller (Ci-Cs)-alkyl, (C3-C5) -cycloalkyl, (C2-Ce) -alkenyl, (C2- Cb)-alkynyl, der hver er substitueret med m radikaler fra gruppen, der består af fluor, chlor, brom, iod, hydroxy og cyano, eller (C1-C6) -alkoxy, (C3-C6) -cycloalkoxy, (C2-C6)-alkenyloxy eller (C2-C6) -alkynyloxy, der hver er substitueret med m radikaler fra gruppen, der består af fluor, chlor, brom, iod, cyano og (Ci-C2) -alkoxy, X5 er hydrogen eller X3; R5 er (C1-C6)-alkyl eller (Cs-Cg)-cycloalkyl, der hver er substitueret med m radikaler fra gruppen, der består af fluor, chlor, brom, iod, cyano og hydroxy; R6 er hydrogen eller R5; R6a er fluor, chlor, brom, rod, cyano, hydroxy, S(0)nR5 eller (C1-C6) -alkoxy, (C2-C6) -alkenyloxy eller (C2-C5) -alkynyloxy, der hver er substitueret med m radikaler fra gruppen, der består af fluor, chlor, brom, cyano og (C1-C2)-alkoxy; R7 er hydrogen eller (C1-C6)-alkyl, (C3-Cg) -cycloalkyl, (C2-C4)- alkenyl eller (C2-C4) -alkynyl, der hver er substitueret med m radikaler fra gruppen, der består af fluor, chlor, brom, cyano og (C1-C2) -alkoxy; R8 er R7; R9 er (C1-C3) -alkyl eller (C1-C3) -alkoxy; k er 3, 4, 5 eller 6; m er 0, 1, 2, 3, 4 eller 5; n er 0, 1 eller 2; p er 0 eller 1; q er 3, 4 eller 5, til bekæmpelse af uønskede planter.
12. Anvendelse af 3-phenylisoxazolin-5-carboxamider eller 3-phenylisoxazolin-5-thioamider ifølge krav 10 eller 11, hvori R1 og R2 uafhængigt af hinanden hver er hydrogen, fluor, chlor, brom, rod, cyano, eller (C1-C4)-alkyl substitueret med i hvert tilfælde m radikaler fra gruppen, der består af fluor, chlor, brom, iod og cyano, R3 er fluor, chlor eller cyano, eller (C1-C6)-alkyl, (C3-C6) -cycloalkyl, (C2-C6) -alkenyl, (C2 — Ce)-alkynyl, der hver er substitueret med m radikaler fra gruppen, der består af fluor og chlor, eller (Ci-Ce)-alkylcarbonyl, der er substitueret med m radikaler fra gruppen, der består af fluor og chlor; R4 er hydrogen, hydroxy eller (Ci-Cs)-alkyl; A er en binding eller en divalent enhed fra gruppen, der består af CH2, CH2CH2, CHCHa, CH2CH2CH2, CH (CH2CH3) , CH(CH3)CH2, C(CH3)2, C(CH3)2CH2, C (iPr) CH3, CH (CH2iPr) CH2, CH2CH=CH, C(CH3)2C=C, CH(CF3)CH2, CH(CH3)CH20, CH2CH20, CH (cPr) CH20, CH(CH2OCH3), CH (CH2CH2SCH3) , CH(COOH), CH(COOCH3), CH(COOH)CH2, CH (COOCH3) CH2, CH2COH(CF3), CH(CONHCH3), CH (CONHCH3)CH2 og CH2CH2CONHCH2 ; Y er O eller S; X er hydrogen, cyano, hydroxy, X1, eller (C1-C12) -alkyl, (C3-C8) -cycloalkyl, (C2-C12) -alkenyl eller (C2-C12) -alkynyl, der hver er substitueret med m radikaler fra gruppen, der består af fluor, chlor, cyano, hydroxy, X1, OX1, NHX1, S(0)nR5, CO2R8, CONRsR8, C0NR8S02Rs og POR9R9; XI er en ring substitueret med n radikaler fra gruppen, der består af R6, R6a, R8 og R9, fra gruppen, der består af
eller phenyl, der er substitueret med n radikaler fra gruppen, der består af R6, R8 og R9; X2, X4 og Xs uafhængigt af hinanden hver er hydrogen, fluor eller chlor, eller (C1-C4) -alkyl eller (C1-C4)-alkoxy, der hver er substitueret med m radikaler fra gruppen, der består af fluor, chlor, cyano og (C1-C4)-alkoxy; X3 er hydrogen, fluor, chlor, brom, cyano, eller (C1-C6) -alkyl, der i hvert tilfælde er substitueret med m radikaler fra gruppen, der består af fluor og chlor; eller (C1-C6) -alkoxy, der er substitueret med m radikaler fra gruppen, der består af fluor og chlor; X5 er hydrogen eller X3; R5 er methyl eller ethyl; R6 er hydrogen eller R5; R5a er fluor, chlor, brom, iod, cyano, hydroxy, S(0)nR5 eller (C1-C6) -alkoxy, (C2-C6) -alkenyloxy eller (C2-Cs) -alkynyloxy, der hver er substitueret med m radikaler fra gruppen, der består af fluor, chlor, brom, cyano og (C1-C2)-alkoxy; R7 er hydrogen eller (C1-C6) -alkyl, der er substitueret med i hvert tilfælde m radikaler fra gruppen, der består af fluor og chlor; R8 er R7; R9 er (C1-C3) -alkoxy; m er 0, 1, 2 eller 3; n er 0, 1 eller 2.
13. Fremgangsmåde til bekæmpelse af uønskede planter, der er kendetegnet ved, at en effektiv mængde af mindst én forbindelse med formel (I) ifølge et hvilket som helst af kravene 1 til 3 eller af mindst én forbindelse med formel (la) ifølge et hvilket som helst af kravene 10 til 12 eller af en herbicid sammensætning ifølge et hvilket som helst af kravene 4 til 9 påføres planterne eller voksestedet for den uønskede vegetation.
14. Anvendelse af forbindelser med formel (I) ifølge et hvilket som helst af kravene 1 til 3 eller af en herbicid sammensætning ifølge et hvilket som helst af kravene 4 til 9 til bekæmpelse af uønskede planter.
15. Anvendelse ifølge et hvilket som helst af kravene 10 til 12 eller 14, der er kendetegnet ved, at forbindelserne med formel (I) anvendes til bekæmpelse af uønskede planter i afgrøder af nytteplanter.
16. Anvendelse ifølge krav 15, der er kendetegnet ved, at nytteplanterne er transgene nytteplanter.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11160613 | 2011-03-31 | ||
| PCT/EP2012/055323 WO2012130798A1 (de) | 2011-03-31 | 2012-03-26 | Herbizid und fungizid wirksame 3-phenylisoxazolin-5-carboxamide und 3- phenylisoxazolin-5-thioamide |
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| US (1) | US9078442B2 (da) |
| EP (1) | EP2691379B1 (da) |
| JP (1) | JP5968999B2 (da) |
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| ES (1) | ES2612694T3 (da) |
| MX (1) | MX350825B (da) |
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2012
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| UA110241C2 (en) | 2015-12-10 |
| JP5968999B2 (ja) | 2016-08-10 |
| AU2012234393A1 (en) | 2013-10-17 |
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| BR112013024629B1 (pt) | 2019-04-16 |
| ES2612694T3 (es) | 2017-05-18 |
| US9078442B2 (en) | 2015-07-14 |
| US20140100108A1 (en) | 2014-04-10 |
| EA024512B1 (ru) | 2016-09-30 |
| EA201391401A1 (ru) | 2014-02-28 |
| EP2691379A1 (de) | 2014-02-05 |
| ZA201306338B (en) | 2014-12-23 |
| PL2691379T3 (pl) | 2017-05-31 |
| EP2691379B1 (de) | 2016-11-02 |
| WO2012130798A1 (de) | 2012-10-04 |
| MX350825B (es) | 2017-09-22 |
| MX2013011217A (es) | 2013-10-17 |
| CN103596936B (zh) | 2016-11-09 |
| CA2831704C (en) | 2019-10-01 |
| AU2012234393B2 (en) | 2017-02-02 |
| WO2012130798A8 (de) | 2013-08-29 |
| AR085737A1 (es) | 2013-10-23 |
| JP2014515015A (ja) | 2014-06-26 |
| CN103596936A (zh) | 2014-02-19 |
| BR112013024629A2 (pt) | 2017-03-21 |
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