3-alkoxybenzamide derivative, and pest control agent
The present invention provides: a 3-alkoxybenzamide derivative having an excellent pest control effect, or a salt thereof; and a pest control agent and a production intermediate which contain the same as an active ingredient. Provided are: a 3-alkoxybenzamide derivative represented by general formula [I] [In the formula, A represents an oxygen atom or a sulfur atom, G represents a hydrogen atom, a halogen atom, or a C 1 -C 6 alkyl group, R 1 represents a C 1 -C 6 alkyl group, a C 3 -C 6 cycloalkyl group, etc., R 2 represents a hydrogen atom, etc., R 3 represents a halogen atom, C 1 -C 6 alkyl group, etc., R 4 represents a halogen atom, C 1 -C 6 alkyl group, etc., and R 5 represents a C 1 -C 12 alkyl group, etc.], or a salt thereof; and a pest control agent characterized by containing said derivative or salt thereof as an active ingredient.
1 . A 3-alkoxybenzamide derivative of formula [I], or an agriculturally acceptable salt thereof,
wherein in the formula [I],
A represents an oxygen atom; or a sulfur atom,
G represents a hydrogen atom,
R 1 represents fluoromethyl; difluoromethyl; trifluoromethyl; chloromethyl; dichloromethyl; trichloromethyl; bromomethyl; dibromomethyl; tribromomethyl; iodomethyl; chlorodifluoromethyl; dichlorofluoromethyl; 1-fluoroethyl; 2-fluoroethyl; 1,1-difluoroethyl; 2,2-difluoroethyl; 2,2,2-trifluoroethyl; 1,1,2,2-tetrafluoroethyl; pentafluoroethyl; 1-chloroethyl; 1,1-dichloroethyl; 2,2-dichloroethyl; 2,2,2-trichloroethyl; 1,1,2,2-tetrachloroethyl; pentachloroethyl; 1-bromoethyl; 2,2,2-tribromoethyl; 1-iodoethyl; 2-iodoethyl; 2-chloro-2,2-difluoroethyl; 2,2-dichloro-2-fluoroethyl; 1-fluoropropyl; 2-fluoropropyl; 3-fluoropropyl; 1,1-difluoropropyl; 2,2-difluoropropyl; 3,3-difluoropropyl; 3,3,3-trifluoropropyl; 2,2,3,3,3-pentafluoropropyl; 1,1,2,3,3,3-hexafluoropropyl; heptafluoropropyl; 1-fluoro-2-propyl; 2-fluoro-2-propyl; 1,1-difluoro-2-propyl; 1,2-difluoro-2-propyl; 1,3-difluoro-2-propyl; 1,2,3-trifluoro-2-propyl; 1,1,3,3-tetrafluoro-2-propyl; 1,1,1,3,3,3-hexafluoro-2-propyl; heptafluoro-2-propyl; 1-chloropropyl; 2-chloropropyl; 3-chloropropyl; 1,1-dichloropropyl; 2,2-dichloropropyl; 3,3-dichloropropyl; 3,3,3-trichloropropyl; 2,2,3,3,3-pentachloropropyl; heptachloropropyl; 1-chloro-2-propyl; 2-chloro-2-propyl; 1,1-dichloro-2-propyl; 1,2-dichloro-2-propyl; 1,3-dichloro-2-propyl; 1,2,3-trichloro-2-propyl; 1,1,3,3-tetrachloro-2-propyl; 1,1,1,3,3,3-hexachloro-2-propyl; heptachloro-2-propyl; 1-bromopropyl; 2-bromopropyl; 3-bromopropyl; 1-bromo-2-propyl; 2-bromo-2-propyl; 1-iodopropyl 2-iodopropyl; 3-iodopropyl; 1-iodo-2-propyl; 2-iodo-2-propyl; 1-fluorobutyl; 2-fluorobutyl; 3-fluorobutyl; 4-fluorobutyl; 4,4-difluorobutyl; 4,4,4-trifluorobutyl; 4,4,4-trifluoro-3-methylbutyl; 3,3,4,4,4-pentafluorobutyl; 2,2,3,4,4,4-hexafluorobutyl; 2,2,3,3,4,4,4-heptafluorobutyl; nonafluorobutyl; 1,1,1-trifluoro-2-butyl; 4,4,4-trifluoro-2-butyl 3,3,4,4,4-pentafluoro-2-butyl; nonafluoro-2-butyl; 1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)-2-propyl; 1-chlorobutyl; 2-chlorobutyl; 3-chlorobutyl; 4-chlorobutyl; 4,4-dichlorobutyl; 4,4,4-trichlorobutyl; nonachlorobutyl; 1,1,1-trichloro-2-butyl; 4,4,4-trichloro-2-butyl; nonachloro-2-butyl; 1-bromobutyl; 2-bromobutyl; 3-bromobutyl; 4-bromobutyl; 1-iodobutyl; 2-iodobutyl; 3-iodobutyl; 4-iodobutyl; 4-chloro-1,1,2,2,3,3,4,4-octafluorobutyl; 4-bromo-1,1,2,2,3,3,4,4-octafluorobutyl; 1-fluoropentyl; 2-fluoropentyl; 3-fluoropentyl; 4-fluoropentyl; 5-fluoropentyl; 5,5,5-trifluoropentyl; 4,4,5,5,5-pentafluoropentyl; 3,3,4,4,5,5,5-heptafluoropentyl; 2,2,3,3,4,4,5,5-octafluoropentyl; 2,2,3,3,4,4,5,5,5-nonafluoropentyl; undecafluoropentyl; 1-chloropentyl; 2-chloropentyl; 3-chloropentyl; 4-chloropentyl; 5-chloropentyl; 5,5,5-trichloropentyl; 4,4,5,5,5-pentachloropentyl; 3,3,4,4,5,5,5-heptachloropentyl; 2,2,3,3,4,4,5,5,5-nonachloropentyl; undecachloropentyl; 1-bromopentyl; 2-bromopentyl; 3-bromopentyl; 4-bromopentyl; 5-bromopentyl; 5-iodopentyl; 1-fluorohexyl; 2-fluorohexyl; 3-fluorohexyl; 4-fluorohexyl; 5-fluorohexyl; 6-fluorohexyl; 6,6,6-trifluorohexyl; 5,5,6,6,6-pentafluorohexyl; 4,4,5,5,6,6,6-heptafluorohexyl; 3,3,4,4,5,5,6,6,6-nonafluorohexyl; 2,2,3,3,4,4,5,5,6,6,6-undecafluorohexyl; 2,2,3,3,4,4,5,5,6,6-decafluorohexyl; tridecafluorohexyl; 1-chlorohexyl; 2-chlorohexyl; 3-chlorohexyl; 4-chlorohexyl; 5-chlorohexyl; 6-chlorohexyl; 5-bromohexyl; 6-bromohexyl; 5-iodohexyl; 6-iodohexyl; a C 3 -C 6 cycloalkyl; a C 3 -C 6 halocycloalkyl; a C 2 -C 6 alkenyl; a C 2 -C 6 alkynyl; a C 1 -C 6 alkoxy; a C 1 -C 6 haloalkoxy; a C 1 -C 6 alkoxy C 1 -C 6 alkyl; a C 3 -C 6 cycloalkyl C 1 -C 6 alkyl; a cyano C 1 -C 6 alkyl; a cyano C 3 -C 6 cycloalkyl; a cyano C 3 -C 6 cycloalkyl C 1 -C 6 alkyl; a cyano heterocycloalkyl; a C 2 -C 6 alkynyl C 3 -C 6 cycloalkyl; a C 1 -C 6 alkoxycarbonyl C 3 -C 6 cycloalkyl; a carboxy C 3 -C 6 cycloalkyl; a carbamoyl C 3 -C 6 cycloalkyl; a C 4 -C 8 bicycloalkyl; a phenyl C 1 -C 6 alkyl, wherein the phenyl moiety is optionally mono-substituted or poly-substituted with R 7 ; or a heteroaryl C 1 -C 3 alkyl, wherein the heteroaryl moiety is optionally mono-substituted or poly-substituted with R 7 ;
R 2 represents a hydrogen atom; a C 1 -C 6 haloalkyl; a C 2 -C 6 alkynyl; a cyano C 1 -C 6 alkyl; a hydroxy C 1 -C 6 alkyl; a C 1 -C 6 alkoxy C 1 -C 6 alkyl; a C 1 -C 6 alkylcarbonyl; a C 1 -C 6 alkoxycarbonyl; a C 1 -C 6 haloalkoxycarbonyl; a C 1 -C 6 alkoxycarbonyl C 1 -C 6 alkyl; an aminocarbonyl C 1 -C 6 alkyl; a C 1 -C 6 alkylaminocarbonyl C 1 -C 6 alkyl, wherein the amino moiety is optionally substituted with R 10 ; a C 1 -C 6 alkylcarbonyloxy C 1 -C 6 alkyl; or a C 1 -C 6 alkoxycarbonyloxy C 1 -C 6 alkyl or
R 1 and R 2 , together with the nitrogen atom to which R 1 and R 2 are attached form a 3- to 8-membered heterocyclic ring or a 3- to 8-membered heterocyclic ring having 1 to 4 heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the formed heterocyclic ring is optionally substituted with a halogen atom, a cyano, a nitro, a C 1 -C 6 alkyl, a C 1 -C 6 alkoxy, a C 1 -C 6 haloalkyl, or an oxo,
R 3 represents a halogen atom; a C 1 -C 6 alkyl; a C 1 -C 6 haloalkyl; or a C 1 -C 6 haloalkoxy,
R 4 represents a hydrogen atom; a halogen atom; or a C 1 -C 6 alkyl,
R 5 represents a C 2 -C 12 alkyl, wherein the C 2 -C 12 alkyl is optionally mono-substituted or poly-substituted with R 6 ; or a C 2 -C 6 alkenyl, wherein the C 2 -C 6 alkenyl is optionally mono-substituted or poly-substituted with R 6 ,
R 6 represents a halogen atom; a C 1 -C 6 alkyl; a C 1 -C 6 haloalkyl; a C 3 -C 6 cycloalkyl; a hydroxy; a thiol; a C 1 -C 6 alkylthio; a C 1 -C 6 haloalkylthio; a C 1 -C 6 alkylsulfinyl; a C 1 -C 6 haloalkylsulfinyl; a C 1 -C 6 alkylsulfonyl; a C 1 -C 6 haloalkylsulfonyl; a C 1 -C 6 alkylcarbonyl; an amino; a C 1 -C 6 alkylcarbonylamino, wherein the amino moiety is optionally substituted with R 10 ; a C 1 -C 6 haloalkylcarbonylamino, wherein the amino moiety is optionally substituted with R 10 ; a C 1 -C 6 alkoxycarbonylamino, wherein the amino moiety is optionally substituted with R 10 ; a C 1 -C 6 haloalkoxycarbonylamino, wherein the amino moiety is optionally substituted with R 10 ; a C 1 -C 6 haloalkylsulfinylamino, wherein the amino moiety is optionally substituted with R 10 ; a C 1 -C 6 haloalkylsulfonylamino, wherein the amino moiety is optionally substituted with R 10 ; a phenylsulfonylamino, wherein the phenyl moiety is optionally mono-substituted or poly-substituted with R 7 , and the amino moiety is optionally substituted with R 10 ; a phenyl, wherein the phenyl is optionally mono-substituted or poly-substituted with R 7 ; an azetidinyl, wherein a nitrogen atom of the azetidinyl is optionally substituted with R 10 ; a 1,3-dioxolanyl; a pyrazolyl, wherein the pyrazolyl is optionally mono-substituted or poly-substituted with R 7 ; a triazolyl, wherein the triazolyl is optionally mono-substituted or poly-substituted with R 7 ; a 1,3-dioxoisoindolinyl, wherein the 1,3-dioxoisoindolinyl is optionally mono-substituted or poly-substituted with R 7 ; or a thiocyanato,
R 7 represents a halogen atom; a C 1 -C 6 alkyl; a C 1 -C 6 haloalkyl; or a cyano, and
R 10 represents a C 1 -C 6 alkyl; a C 1 -C 6 haloalkyl; a C 3 -C 6 cycloalkyl; a C 1 -C 6 alkoxy C 1 -C 6 alkyl; a C 1 -C 6 alkoxy C 1 -C 6 alkoxy C 1 -C 6 alkyl; a C 1 -C 6 alkylthio C 1 -C 6 alkyl; a C 1 -C 6 alkylsulfonyl C 1 -C 6 alkyl; a cyano C 1 -C 6 alkyl; a C 1 -C 6 alkylcarbonyl; a C 1 -C 6 alkoxycarbonyl; a C 1 -C 6 haloalkylsulfonyl; a C 1 -C 6 alkylcarbonyl C 1 -C 6 alkyl; a C 1 -C 6 alkoxycarbonyl C 1 -C 6 alkyl; a C 1 -C 6 alkylcarbonyloxy C 1 -C 6 alkyl; a C 1 -C 6 alkoxycarbonyloxy C 1 -C 6 alkyl; or a 5-methyl-1,3-dioxole-2-one-4-ylmethyl.
2 . An agrochemical composition comprising the 3-alkoxybenzamide derivative or the agriculturally acceptable salt thereof according to claim 1 as an active ingredient.
3 . The agrochemical composition according to claim 2 , which further comprises a surfactant.
4 . The agrochemical composition according to claim 2 , wherein the agrochemical composition is capable of controlling pests in a paddy field, a dry field, a lawn, an orchard, a non-crop land, a greenhouse, a seedling raising facility, and a plant factory where an agricultural or horticultural plant is cultivated.
5 . The agrochemical composition according to claim 4 , wherein the agricultural or horticultural plant is a plant to which resistance is imparted by a breeding or genetic modification techniques.
6 . A hydroxybenzamide derivative of formula [II], or a salt thereof,
wherein in the formula [II],
A represents an oxygen atom or a sulfur atom,
G represents a hydrogen atom,
R 1 represents an n-propyl; a sec-butyl; an isobutyl; a tert-butyl; an n-pentyl; a 1-methylbutyl; a 2-methylbutyl; a 3-methylbutyl; an 1-ethylpropyl; a 1,1-dimethylpropyl; a 1,2-dimethylpropyl; a neopentyl; an n-hexyl; a 1-methylpentyl; a 2-methylpentyl; a 3-methylpentyl; a 4-methylpentyl; a 1-ethylbutyl; a 2-ethylbutyl; a 1,1-dimethylbutyl; a 1,2-dimethylbutyl; a 1,3-dimethylbutyl; a 2,2-dimethylbutyl; a 2,3-dimethylbutyl; a 3,3-dimethylbutyl; a 1,1,2-trimethylpropyl; a 1,2,2-trimethylpropyl; 1-ethyl-1-methylpropyl; a 1-ethyl-2-methylpropyl; fluoromethyl; difluoromethyl; trifluoromethyl; chloromethyl; dichloromethyl; trichloromethyl; bromomethyl; dibromomethyl; tribromomethyl; iodomethyl; chlorodifluoromethyl; dichlorofluoromethyl; 1-fluoroethyl; 2-fluoroethyl; 1,1-difluoroethyl; 2,2-difluoroethyl; 2,2,2-trifluoroethyl; 1,1,2,2-tetrafluoroethyl; pentafluoroethyl; 1-chloroethyl; 2-chloroethyl; 1,1-dichloroethyl; 2,2-dichloroethyl; 2,2,2-trichloroethyl; 1,1,2,2-tetrachloroethyl; pentachloroethyl; 1-bromoethyl; 2-bromoethyl; 2,2,2-tribromoethyl; 1-iodoethyl; 2-iodoethyl; 2-chloro-2,2-difluoroethyl; 2,2-dichloro-2-fluoroethyl; 1-fluoropropyl; 2-fluoropropyl; 3-fluoropropyl; 1,1-difluoropropyl; 2,2-difluoropropyl; 3,3-difluoropropyl; 3,3,3-trifluoropropyl; 2,2,3,3,3-pentafluoropropyl; 1,1,2,3,3,3-hexafluoropropyl; heptafluoropropyl; 1-fluoro-2-propyl; 2-fluoro-2-propyl; 1,1-difluoro-2-propyl; 1,2-difluoro-2-propyl; 1,3-difluoro-2-propyl; 1,2,3-trifluoro-2-propyl; 1,1,3,3-tetrafluoro-2-propyl; 1,1,1,3,3,3-hexafluoro-2-propyl; heptafluoro-2-propyl; 1-chloropropyl; 3-chloropropyl; 1,1-dichloropropyl; 2,2-dichloropropyl; 3,3-dichloropropyl; 3,3,3-trichloropropyl; 2,2,3,3,3-pentachloropropyl; heptachloropropyl; 2-chloro-2-propyl; 1,1-dichloro-2-propyl; 1,2-dichloro-2-propyl; 1,3-dichloro-2-propyl; 1,2,3-trichloro-2-propyl; 1,1,3,3-tetrachloro-2-propyl; 1,1,1,3,3,3-hexachloro-2-propyl; heptachloro-2-propyl; 1-bromopropyl; 2-bromopropyl; 3-bromopropyl; 1-bromo-2-propyl; 2-bromo-2-propyl; 1-iodopropyl; 2-iodopropyl; 3-iodopropyl; 1-iodo-2-propyl; 2-iodo-2-propyl; 1-fluorobutyl; 2-fluorobutyl; 3-fluorobutyl; 4-fluorobutyl, 4,4-difluorobutyl; 4,4,4-trifluorobutyl; 4,4,4-trifluoro-3-methylbutyl; 3,3,4,4,4-pentafluorobutyl; 2,2,3,4,4,4-hexafluorobutyl; 2,2,3,3,4,4,4-heptafluorobutyl; nonafluorobutyl; 1,1,1-trifluoro-2-butyl; 4,4,4-trifluoro-2-butyl, 3,3,4,4,4-pentafluoro-2-butyl; nonafluoro-2-butyl; 1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)-2-propyl; 1-chlorobutyl; 2-chlorobutyl; 3-chlorobutyl; 4-chlorobutyl; 4,4-dichlorobutyl; 4,4,4-trichlorobutyl; nonachlorobutyl; 1,1,1-trichloro-2-butyl; 4,4,4-trichloro-2-butyl; nonachloro-2-butyl; 1-bromobutyl; 2-bromobutyl; 3-bromobutyl; 4-bromobutyl; 1-iodobutyl; 2-iodobutyl; 3-iodobutyl; 4-iodobutyl; 4-chloro-1,1,2,2,3,3,4,4-octafluorobutyl; 4-bromo-1,1,2,2,3,3,4,4-octafluorobutyl; 1-fluoropentyl; 2-fluoropentyl; 3-fluoropentyl; 4-fluoropenty; 5-fluoropentyl, 5,5,5-trifluoropentyl; 4,4,5,5,5-pentafluoropentyl; 3,3,4,4,5,5,5-heptafluoropentyl; 2,2,3,3,4,4,5,5-octafluoropentyl; 2,2,3,3,4,4,5,5,5-nonafluoropentyl; undecafluoropentyl; 1-chloropentyl; 2-chloropentyl; 3-chloropentyl; 4-chloropentyl; 5-chloropentyl; 5,5,5-trichloropentyl; 4,4,5,5,5-pentachloropentyl; 3,3,4,4,5,5,5-heptachloropentyl; 2,2,3,3,4,4,5,5,5-nonachloropentyl; undecachloropentyl; 1-bromopentyl; 2-bromopentyl; 3-bromopentyl; 4-bromopentyl; 5-bromopentyl; 5-iodopentyl; 1-fluorohexyl; 2-fluorohexyl; 3-fluorohexyl; 4-fluorohexyl; 5-fluorohexyl; 6-fluorohexyl; 6,6,6-trifluorohexyl; 5,5,6,6,6-pentafluorohexyl; 4,4,5,5,6,6,6-heptafluorohexyl; 3,3,4,4,5,5,6,6,6-nonafluorohexyl; 2,2,3,3,4,4,5,5,6,6,6-undecafluorohexyl; 2,2,3,3,4,4,5,5,6,6-decafluorohexyl; tridecafluorohexyl; 1-chlorohexyl; 2-chlorohexyl; 3-chlorohexyl; 4-chlorohexyl; 5-chlorohexyl; 6-chlorohexyl; 5-bromohexyl; 6-bromohexyl; 5-iodohexyl; and 6-iodohexyl; a C 3 -C 6 cycloalkyl; a C 3 -C 6 halocycloalkyl; a C 2 -C 6 alkenyl; a C 2 -C 6 alkynyl; a C 1 -C 6 alkoxy; a C 1 -C 6 haloalkoxy; a C 1 -C 6 alkoxy C 1 -C 6 alkyl; a C 3 -C 6 cycloalkyl C 1 -C 6 alkyl; a cyano C 1 -C 6 alkyl; a cyano C 3 -C 6 cycloalkyl; a cyano C 3 -C 6 cycloalkyl C 1 -C 6 alkyl; a cyano heterocycloalkyl; a C 2 -C 6 alkynyl C 3 -C 6 cycloalkyl; a C 1 -C 6 alkoxycarbonyl C 3 -C 6 cycloalkyl; a carboxy C 3 -C 6 cycloalkyl; a carbamoyl C 3 -C 6 cycloalkyl; a C 4 -C 8 bicycloalkyl; a phenyl, wherein the phenyl is mono-substituted or poly-substituted with R 7 ; a phenyl C 1 -C 6 alkyl, wherein the phenyl moiety is optionally mono-substituted or poly-substituted with R 7 ; or a heteroaryl C 1 -C 3 alkyl, wherein the heteroaryl moiety is optionally mono-substituted or poly-substituted with R 7 ;
R 2 represents a hydrogen atom; a C 2 -C 6 alkyl; a C 1 -C 6 haloalkyl; a C 2 -C 6 alkynyl; a cyano C 1 -C 6 alkyl; a hydroxy C 1 -C 6 alkyl; a C 1 -C 6 alkoxy C 1 -C 6 alkyl; a C 1 -C 6 alkylcarbonyl; a C 1 -C 6 alkoxycarbonyl; a C 1 -C 6 haloalkoxycarbonyl; a C 1 -C 6 alkoxycarbonyl C 1 -C 6 alkyl; an aminocarbonyl C 1 -C 6 alkyl; a C 1 -C 6 alkylaminocarbonyl C 1 -C 6 alkyl, wherein the amino moiety is optionally substituted with R 10 ; a C 1 -C 6 alkylcarbonyloxy C 1 -C 6 alkyl; or a C 1 -C 6 alkoxycarbonyloxy C 1 -C 6 alkyl, or
R 1 and R 2 , together with the nitrogen atom to which R 1 and R 2 are attached form a 3- to 8-membered heterocyclic ring or a 3- to 8-membered heterocyclic ring having 1 to 4 heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, and the heterocyclic ring is optionally substituted with a halogen atom, a cyano, a nitro, a C 1 -C 6 alkyl, a C 1 -C 6 alkoxy, a C 1 -C 6 haloalkyl, or an oxo,
R 3 represents a fluorine atom; a chlorine atom; a bromine atom; a C 1 -C 6 alkyl; a C 1 -C 6 haloalkyl; or a C 1 -C 6 haloalkoxy,
R 4 represents a hydrogen atom; a halogen atom; or a C 1 -C 6 alkyl,
R 7 represents a halogen atom; a C 1 -C 6 alkyl; a C 1 -C 6 haloalkyl; or a cyano, and
R 10 represents a C 1 -C 6 alkyl; a C 1 -C 6 haloalkyl; a C 3 -C 6 cycloalkyl; a C 1 -C 6 alkoxy C 1 -C 6 alkyl; a C 1 -C 6 alkoxy C 1 -C 6 alkoxy C 1 -C 6 alkyl; a C 1 -C 6 alkylthio C 1 -C 6 alkyl; a C 1 -C 6 alkylsulfonyl C 1 -C 6 alkyl; a cyano C 1 -C 6 alkyl; a C 1 -C 6 alkylcarbonyl; a C 1 -C 6 alkoxycarbonyl; a C 1 -C 6 haloalkylsulfonyl; a C 1 -C 6 alkylcarbonyl C 1 -C 6 alkyl; a C 1 -C 6 alkoxycarbonyl C 1 -C 6 alkyl; a C 1 -C 6 alkylcarbonyloxy C 1 -C 6 alkyl; a C 1 -C 6 alkoxycarbonyloxy C 1 -C 6 alkyl; or a 5-methyl-1,3-dioxole-2-one-4-ylmethyl.