Amides and thioamides as pesticides
View Patent ↗The present application relates to novel amides and thioamides, to processes for preparation thereof and to use thereof for controlling animal pests, in particular arthropods and especially insects.
1. A compound of the formula (I)
in which
G is CH, C-halogen, C-nitro, C-cyano, C—C 1 -C 6 -haloalkyl, C—C 3 -C 6 -cycloalkyl, C—C 1 -C 6 -alkoxy, or C—C 1 -C 6 -haloalkoxy,
R 1 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, halogen, cyano, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, amino, C 1 -C 6 -alkylamino, di(C 1 -C 6 )-alkylamino or C 1 -C 6 -thioalkyl,
X is oxygen or sulphur,
R 2 is a radical selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 2 -C 4 -alkenyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, optionally halogen-substituted C 1 -C 4 -alkylcarbonyl, optionally halogen-substituted C 1 -C 4 -alkoxycarbonyl and optionally halogen-substituted C 3 -C 6 -cycloalkylcarbonyl,
and
R 3 is a radical selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, cyano-C 1 -C 6 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 2 -C 4 -haloalkynyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, optionally halogen-substituted C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, optionally halogen-substituted bis(C 1 -C 6 -alkoxy)-C 1 -C 6 -alkyl, optionally halogen-substituted C 1 -C 6 -alkylthio-C 1 -C 6 -alkyl, optionally halogen-substituted C 1 -C 4 -alkylcarbonyl-C 1 -C 6 -alkyl, optionally halogen-substituted C 1 -C 6 -alkylsulphinyl-C 1 -C 6 -alkyl, optionally halogen-substituted C 1 -C 6 -alkyl sulphonyl-C 1 -C 6 -alkyl, optionally halogen-substituted C 1 -C 6 -alkoxycarbonyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxycarbonylamino optionally C 1 -C 6 -alkyl-substituted on the nitrogen, C 2 -C 4 -alkynyloxy, C 2 -C 4 -alkynyloxycarbonyl, optionally halogen-, cyano-, C 1 -C 6 -alkyl-, C 1 -C 6 -haloalkyl-, C 1 -C 6 -alkoxy-, C 1 -C 6 -haloalkoxy-, C 1 -C 6 -alkoxycarbonyl-, or C 1 -C 6 -haloalkoxycarbonyl-substituted C 3 -C 6 -cycloalkyl, optionally halogen-, cyano-, C 1 -C 6 -alkyl-, C 1 -C 6 -haloalkyl-, C 1 -C 6 -alkoxy-, C 1 -C 6 -haloalkoxy-, C 1 -C 6 -alkoxycarbonyl-, or C 1 -C 6 -haloalkoxycarbonyl-substituted C 3 -C 6 -cycloalkylcarbonyl, optionally halogen-, cyano-, C 1 -C 6 -alkyl-, C 1 -C 6 -haloalkyl-, C 1 -C 6 -alkoxy-, C 1 -C 6 -haloalkoxy-, C 1 -C 6 -alkoxycarbonyl-, or C 1 -C 6 -haloalkoxycarbonyl-substituted C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl, optionally halogen-, cyano-, C 1 -C 6 -alkyl-, C 1 -C 6 -alkoxy- or C 1 -C 6 -haloalkoxy-substituted aryl-C 1 -C 6 -alkyl, optionally in the aryl moiety, halogen-substituted aryloxy-C 1 -C 6 -alkyl, and NR 4 R 5 in which R 4 and R 5 are each independently a radical selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl and C 1 -C 6 -alkoxycarbonyl,
and
a salt and a N-oxide of the compound of the formula (I).
2. A composition, comprising at least one compound of the formula (I) according to claim 1 and one or more extenders, surfactants, and combinations thereof.
3. A method for controlling insects or arthropods, comprising contacting an effective amount of a compound of the formula (I) according to claim 1 with one or more insects or arthropods, their habitat, or combinations thereof.
4. The compound according to claim 1 ,
in which
G is CH, C-halogen, C-nitro, C-cyano, C—C 1 -C 4 alkyl, C—C 1 -C 4 -haloalkyl, C—C 3 -C 6 -cycloalkyl, C—C 1 -C 4 -alkoxy, or C—C 1 -C 4 -haloalkoxy,
R 1 is hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, halogen, cyano, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, amino, C 1 -C 4 -alkylamino, di(C 1 -C 4 )-alkylamino or C 1 -C 4 -thioalkyl,
X is oxygen or sulphur,
R 2 is a radical selected from the group consisting of hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 2 -C 3 -alkenyl, C 1 -C 2 -alkoxy-C 1 -C 2 -alkyl, C 1 -C 2 -alkylcarbonyl, C 1 -C 2 -alkoxycarbonyl, and in each case optionally halogen-substituted cyclopropylcarbonyl, cyclopentylcarbonyl or cyclohexylcarbonyl,
R 3 is a radical selected from the group consisting of hydrogen, C 1 -C 4 -alkyl, C 1 -C 5 -haloalkyl, cyano-C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 2 -C 4 -haloalkynyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, optionally halogen-substituted C 1 -C 2 -alkoxy-C 1 -C 4 -alkyl, optionally halogen-substituted bis(C 1 -C 2 -alkoxy)-C 1 -C 4 -alkyl, optionally halogen-substituted C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, optionally halogen-substituted C 1 -C 4 -alkylcarbonyl-C 1 -C 4 -alkyl, optionally halogen-substituted C 1 -C 4 -alkylsulphinyl-C 1 -C 4 -alkyl, optionally halogen-substituted C 1 -C 4 -alkylsulphonyl-C 1 -C 4 -alkyl, optionally halogen-substituted C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonylamino optionally C 1 -C 4 -alkyl-substituted on the nitrogen, C 2 -C 4 -alkynyloxy, C 2 -C 4 -alkynyloxycarbonyl, optionally halogen-, cyano-, C 1 -C 4 -alkyl-, C 1 -C 4 -haloalkyl-, C 1 -C 4 -alkoxy-, C 1 -C 4 -haloalkoxy-, C 1 -C 4 -alkoxycarbonyl-, or C 1 -C 4 -haloalkoxycarbonyl-substituted C 3 -C 6 -cycloalkyl, optionally halogen-, cyano-, C 1 -C 4 -alkyl-, C 1 -C 4 -haloalkyl-, C 1 -C 4 -alkoxy-, C 1 -C 4 -haloalkoxy-, C 1 -C 4 -alkoxycarbonyl-, or C 1 -C 4 -haloalkoxycarbonyl-substituted C 3 -C 6 -cycloalkylcarbonyl, optionally halogen-, cyano-, C 1 -C 4 -haloalkyl-, C 1 -C 4 -alkoxy-, C 1 -C 4 -haloalkoxy-, C 1 -C 4 -alkoxycarbonyl-, or C 1 -C 4 -haloalkoxycarbonyl-substituted C 3 -C 6 -cycloalkyl-C 4 -C 4 -alkyl, optionally halogen-, cyano-, C 1 -C 4 -alkyl-, C 1 -C 4 -haloalkyl-, C 1 -C 4 -alkoxy- or C 1 -C 4 -haloalkoxy-substituted aryl-C 1 -C 4 -alkyl, aryloxy-C 1 -C 4 -alkyl optionally halogen-substituted in the aryl moiety.
5. The compound according to claim 1 ,
in which
G is CH, C-halogen, C-cyano, C—CH 3 , C—CF 3 , C-cyclopropyl, C—OCH 3 , or C—OCF 3 ,
R 1 is hydrogen, methyl, trifluoromethyl, cyclopropyl, halogen, cyano, methoxy, trifluoromethoxy, amino, methylamino, or dimethylamino,
X is oxygen or sulphur,
R 2 is a radical selected from the group consisting of hydrogen, methyl, ethyl, CH 2 CF 3 , CH 2 CF 2 CH 3 , CH 2 CHF 2 , CH 2 CF 2 CHF 2 , CH 2 CH 2 F, CH 2 —CHFCH 3 , CH 2 CF 2 Br, CH 2 CFCl 2 , CH(CH 3 )CH 2 F, CH 2 CCl 3 , CH 2 CClF 2 , CH 2 CH 2 CH 2 F, CH 2 CH(CH 3 )Cl, CHCF 3 CH(CH 3 ) 2 , CH(CF 3 ) 2 , CH 2 CH 2 Cl, CHCF 3 CH 2 CH 2 CH 3 , CH 2 CF 2 CF 3 , methoxy, ethoxy, vinyl, CH 2 OCH 3 , CH 2 OCH 2 CH 3 , methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, cyclopropylcarbonyl and fluorocyclopropylcarbonyl,
and
R 3 is a radical selected from the group consisting of hydrogen, methyl, ethyl, CH 2 CF 3 , CH 2 CH 2 CF 3 , CH 2 CF 2 CH 3 , CH 2 CHF 2 , CH 2 CF 2 CHF 2 , CH 2 CH 2 F, CH 2 CHFCH 3 , CH 2 CF 2 Br, CH 2 CFCl 2 , CH(CH 3 )CH 2 F, CH 2 CCl 3 , CH 2 CClF 2 , CH 2 CH 2 CH 2 F, CH 2 CH(CH 3 )Cl, CHCF 3 CH(CH 3 ) 2 , CH(CF 3 ) 2 , CH 2 CH 2 Cl, CHCF 3 CH 2 CH 2 CH 3 , CH 2 CF 2 CF 3 , C(CH 3 ) 2 CN, CH(CN)CH(CH 3 ) 2 , CH 2 CN, CH 2 CH 2 CN, vinyl, C(CH 3 ) 2 CCH, CH 2 CCCH 3 , methoxy, ethoxy, CH 2 CH(OCH 3 ) 2 , CH 2 CH(CH 3 )(OCH 3 ), CH 2 C(CH 3 ) 2 (OCH 3 ), CH(CH 3 )CH(OCH 3 ) 2 , CH 2 C(CH 3 )(OCH 3 ) 2 , C(CH 3 ) 2 —CH 2 SCH 3 , CH 2 CH 2 SCH 3 , CHCH 3 CH 2 SCH 3 , optionally halogen-substituted C 1 -C 4 -alkylcarbonyl-C 1 -C 4 -alkyl, CH 3 SO 2 CH 2 C(CH 3 ) 2 , CH 3 SO 2 CH 2 CHCH 3 , propargyloxy, cyclopropyl, cyanocyclopropyl, fluorocyclopropyl, trifluoromethylcyclopropyl, trifluoromethylcyclohexyl, methoxycarbonylcyclopropyl, fluorocyclopropylcarbonyl, cyclopropylmethyl, 1-cyclopropylethyl, cyclohexylmethyl, 1-cyano-1-cyclopropyleth-1-yl, optionally halogen-, cyano-, methyl-, ethyl-, methoxy- or ethoxy-substituted benzyl, methoxycarbonylethyl, methoxycarbonylamino, 4,6-dimethoxypyrimid-2-ylmethyl, 2-(2,5-dichlorophenoxy)ethyl and N-methyl-N-methoxycarbonyl-amino.