Heteroaryl-triazole and heteroaryl-tetrazole compounds as pesticides
The present invention relates to novel heteroaryl-triazole and heteroaryl-tetrazole compounds of the general formula (I), in which the structural elements Y, Q 1 , Q 2 , R 1 , R 2 , R 3a , R 3b , R 4 and R 5 have the meaning given in the description, to formulations and compositions comprising such compounds and for their use in the control of animal pests including arthropods and insects in plant protection and to their use for control of ectoparasites on animals.
1. A compound of formula (I)
wherein
X is O or S;
Q 1 is N
Q 2 is CR 5
Y is a direct bond or CH 2 ;
R 1 is hydrogen, methyl, ethyl, 2-(trimethylsilyl) ethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 3,3,3-trifluoropropyl, or cyclopropyl-CH 2 —;
R 2 3-chloro-5-(methylsulfonyl)phenyl, 3-methylsulfonyl-5-(trifluoromethyl)phenyl, 5-(methylsulfonyl) pyridin-3-yl, 3-(methylsulfonyl)phenyl, 3-(trifluoromethylsulfonyl)phenyl, 5-[(trifluoromethyl)sulfonyl]pyridin-3-yl, 3-chloro-5-[(cyclopropylamino)carbonyl]phenyl, 3-cyclopropyl-5-(trifluoromethyl)phenyl, 3-phenyl-5-(trifluoromethyl)phenyl, 3-(4-fluorophenyl)-5-(trifluoromethyl)phenyl, 3-fluoro-5-(trifluoromethylsulfonyl)phenyl, 3-chloro-5-(trifluoromethylsulfonyl)phenyl, 5-chloro-3-thienyl, 3,4,5-trichloro-2-thienyl, 2,5-dichloro-3-thienyl, 4,5-dichloro-2-thienyl, 1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl, 4-chloro-1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl, 5-methyl-1,2-oxazol-3-yl, 5-cyclopropyl-1,2-oxazol-3-yl, 3-chloro-1,2-oxazol-5-yl, 2-chloro-1,3-thiazol-5-yl, 1-methyl-1H-pyrazol-4-yl, 5-chloro-1-methyl-1H-pyrazol-4-yl, 3-chloro-5-cyclopropylsulfonylphenyl, 3-chloro-5-(4-fluorophenyl)sulfonylphenyl, 3-chloro-5-ethylsulfonylphenyl, 3-cyclopropyl-5-fluorophenyl, 3-chloro-5-(isopropylthio)phenyl, 3-chloro-5-(1H-pyrazol-1-yl)phenyl, 3-chloro-5-(1H-1,2,4-triazol-1-yl)phenyl, 3-fluoro-5-cyclopropylphenyl, 3-chloro-5-cyclopropylphenyl, 3-chloro-5-isopropylsulfonylphenyl, 1-(4-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl, 3-cyclopropyl-5-(trifluoromethoxy)phenyl, 4-(trifluoromethylsulfonyl)phenyl, 3-chloro-5-[1-(methoxyimino) ethyl]phenyl, 3-(tert-butylthio)-5-chlorophenyl, 1-(4-fluorophenyl)-1H-pyrazol-4-yl, 1-(4-fluorophenyl)-5-(trifluoromethyl)-1H-pyrazol-3-yl, 5-[4-(trifluoromethoxy)phenyl]pyridin-3-yl, 3-chloro-5-methylsulfanylphenyl, 3-chloro-5-methylsulfinylphenyl, 3-benzamido-5-chlorophenyl, 3-(tert-butylsulfonyl)-5-chlorophenyl, 5-[4-(trifluoromethyl)phenyl]-pyridin-3-yl, 5-[4-(trifluoromethoxy)phenyl]-pyridin-3-yl, 5-(4-chlorophenyl) pyridin-3-yl, 5-(4-fluorophenyl)pyridin-3-yl, 3-chloro-5-[(phenylsulfonyl)amino]phenyl, 3-acetamido-5-chlorophenyl, 3-chloro-5-[(cyclopropylcarbonyl)amino]phenyl, 3-chloro-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl, 3-chloro-5-[(2,2,2-trifluoroethyl)sulfonyl]phenyl, 3-chloro-5-[3-(trifluoromethyl)-1H-pyrazol-1-yl]phenyl, 3,5-bis(methylsulfonyl)phenyl, pyrazolo[1,5-a]pyridin-2-yl, 7-(trifluoromethyl)pyrazolo[1,5-a]pyridin-2-yl, 6-chloropyrazolo[1,5-a]pyridin-2-yl, 3-[4′-(trifluoromethoxy)phenyl]-phenyl, 3-(4′-fluorophenyl)-5-(trifluoromethyl)phenyl or 3-chloro-5-(1-cyanocyclopropyl)phenyl;
R 3a , R 3b are independently hydrogen, methyl or methoxymethyl wherein R 3a and R 3b are not both hydrogen;
or
R 3a and R 3b form together with the carbon to which they are connected a cyclopropane ring;
R 4 is pyridin-2-yl, pyrimidin-2-yl, pyrimidin-4-yl, 5-fluoropyrimidin-2-yl, 5-chloropyrimidin-2-yl, 5-cyanopyrimidin-2-yl, 5-(trifluoromethyl)pyrimidin-2-yl, 5-methylpyrimidin-2-yl, 5-fluoropyridin-2-yl, 5-chloropyridin-2-yl, 2-chloropyridin-4-yl, 5-cyanopyridin-2-yl, 4-cyano-pyridin-2-yl, 6-cyano-pyridin-2-yl, 5-methoxy-pyridin-2-yl, 5-(trifluoromethyl)-pyridin-2-yl, 5-(difluoromethoxy)pyridin-2-yl, 5-(trifluoromethylthio)pyridin-2-yl, 5-nitropyridin-2-yl, 5-aminopyridin-2-yl, 3,5-difluoropyridin-2-yl, 5-chloro-3-fluoropyridin-2-yl, pyridin-2-yl-5-carboxylic acid, methyl pyridin-2-yl-5-carboxylate, N-methyl-pyridin-2-yl-5-carboxamide, N-cyclopropyl-pyridin-2-yl-5-carboxamide, N-cyclopropyl-N-methyl-pyridin-2-yl-5-carboxamide, N-(1-cyanocyclopropyl)-pyridin-2-yl-5-carboxamide, N-(2,2-difluoroethyl)-pyridin-2-yl-5-carboxamide, N-(2,2,2-trifluoroethyl)-pyridin-2-yl-5-carboxamide, N-methylsulfonyl-pyridin-2-yl-5-carboxamide, N-(4-fluorophenyl)-pyridin-2-yl-5-carboxamide, 5-acetamidopyridin-2-yl, 5-(trifluoroacetamido)-pyridin-2-yl, 5-(2-cyanoacetylamino)-pyridin-2-yl, 5-[(cyclopropylcarbonyl)amino]pyridin-2-yl, 5-[(1-cyanocyclopropylcarbonyl)amino]-pyridin-2-yl, 5-(methanesulfonamido)-pyridin-2-yl, 5-(trifluoromethylsulfonamido)-pyridin-2-yl, 5-[(4-fluorobenzoyl)amino]pyridine-2-yl pyrazin-2-yl, 2-cyano-pyrazin-5-yl, or 1,3-thiazol-2-yl;
R 5 is hydrogen, methyl or trifluoromethyl.
2. A formulation comprising at least one compound of formula (I) according to claim 1 .
3. The formulation according to claim 2 , further comprising at least one extender and/or at least one surface-active substance.
4. The formulation according to claim 2 , wherein the compound of formula (I) is in a mixture with at least one further active compound.
5. A product comprising a compound of formula (I) according to claim 1 or of a formulation thereof effective in controlling one or more animal pests.
6. The product according to claim 5 , wherein the animal pests is an insect, an arachnid or a nematode.
7. A method for controlling one or more pests comprising allowing a compound of formula (I) according to claim 1 or a formulation thereof to act on the pests and/or a habitat thereof.
8. The method according to claim 7 , wherein the pests is an animal pest.
9. A method for protecting seed or a germinating plant from one or more pests comprising contacting the seed with the compound of formula (I) according to claim 1 or with a formulation comprising the compound of formula (I).
10. A plant seed obtained by the method according to claim 9 .