Heterocyclic compounds as pesticides
View Patent ↗The present application relates to novel amides and thioamides, to processes for preparation thereof and to the use thereof for controlling animal pests, in particular arthropods and especially insects.
1. A compound of formula (I), a salt thereof, or an N-oxide thereof,
in which
A 1 and A 2 are each independently hydrogen, halogen, cyano, nitro, alkyl, cycloalkyl or alkoxy,
G 1 is N or C-A 1 , and
G 2 is a radical selected from the group consisting of
in which the arrow marks the bond to the adjacent ring,
R 1 in heterocycles (A) and (D) is hydrogen, halogen, cyano, alkyl, alkoxy, amino, alkylamino, dialkylamino, alkylthio or haloalkyl, and
R 1 in heterocycle (C) is hydrogen, alkyl or haloalkyl,
B is hydrogen, halogen, cyano, nitro, alkyl, cycloalkyl, haloalkyl, amino, alkylamino, dialkylamino, alkylthio or alkoxy, and
G 3 is a radical
in which the arrow marks the bond to G 2 and the radical (E), can be combined with the heterocycles (A), (B), (C) and (D),
X is oxygen or sulphur,
n is 1 or 2,
R 2 is hydrogen, alkyl, haloalkyl, cyanoalkyl, alkoxy, haloalkoxy, alkenyl, alkoxyalkyl, optionally halogen-substituted alkylcarbonyl, optionally halogen-substituted alkoxycarbonyl, optionally halogen-, alkyl-, alkoxy-, haloalkyl- and/or cyano-substituted cycloalkylcarbonyl, or a cation,
R 7 is an optionally substituted alkyl, alkenyl, or alkynyl, an optionally substituted cycloalkyl, cycloalkylalkyl, or cycloalkenyl, in which the rings optionally contain at least one heteroatom selected from the group consisting of sulphur, oxygen (where oxygen atoms must not be immediately adjacent), nitrogen, and combinations thereof, an optionally substituted aryl, heteroaryl, arylalkyl or heteroarylalkyl, or an optionally substituted amino group, or
R 2 and R 7 form, together with the N—S(O) n group in the radical (E) to which they are bonded, a saturated or unsaturated and optionally substituted 4- to 8-membered ring which optionally contain one or more further heteroatoms selected from the group consisting of sulphur, oxygen (where oxygen atoms must not be immediately adjacent), nitrogen, and combinations thereof, and optionally contain at least one carbonyl group.
2. A composition comprising a compound of formula (I), a salt thereof, or an N-oxide thereof, of claim 1 , and an extender, a surfactant, or a combination thereof.
3. A method of controlling pests, comprising applying a compound of formula (I), of claim 1 , to the pests, their habitat, or a combination thereof.
4. A method of controlling pests, comprising applying a salt of the compound of formula (I), of claim 1 , to the pests, their habitat or a combination thereof.
5. The compound of formula (I), of claim 1 .
6. The N-oxide of the compound of formula (I), of claim 1 .
7. The salt of the compound of formula (I), of claim 1 .
8. The composition of claim 2 , comprising the extender.
9. The composition of claim 2 , comprising the surfactant.
10. The composition of claim 2 , comprising the extender and the surfactant.
11. A method of controlling pests, comprising applying an N-oxide of the compound of formula (I), of claim 1 , to the pests, their habitat, or a combination thereof.
12. A method of making a composition, comprising combining a compound of formula (I), a salt thereof, or an N-oxide thereof, of claim 1 , and an extender, a surfactant, or a combination thereof.
13. A method of controlling pests, comprising applying the composition of claim 2 , to the pests, their habitat, or a combination thereof.
14. A composition, comprising a compound of formula (I), of claim 1 , and an extender, a surfactant, or a combination thereof.
15. A composition, comprising a salt of the compound of formula (I), of claim 1 , and an extender, a surfactant, or a combination thereof.
16. A composition, comprising an N-oxide of the compound of formula (I), of claim 1 , and an extender, a surfactant, or a combination thereof.
17. A method of protecting crops, comprising applying the compound of formula (I), the salt thereof, or the N-oxide thereof, of claim 1 , to the crops.
18. A method of protecting crops, comprising applying the compound of formula (I), of claim 1 , to the crops.
19. A method of protecting crops, comprising applying the salt of the compound of formula (I), of claim 1 , to the crops.
20. A metal complex of the compound of formula (I), of claim 1 .
21. A compound of formula (I), a salt thereof, or an N-oxide thereof, of claim 1 , in which
A 1 and A 2 are each independently hydrogen, halogen, cyano, nitro, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl or C 1 -C 6 -alkoxy,
R 1 in the case of the heterocycles (A) and (D) is hydrogen, halogen, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy or C 1 -C 6 -haloalkyl,
R 1 in the case of heterocycle (C) is hydrogen, C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl,
B is hydrogen, halogen, cyano, nitro, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl C 1 -C 6 -alkoxy or C 3 -C 6 -cycloalkyl,
R 2 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, cyano-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, optionally halogen-substituted C 1 -C 6 -alkylcarbonyl optionally halogen-substituted C 1 -C 6 -alkoxycarbonyl, optionally halogen-, C 1 -C 6 -alkyl-, C 1 -C 6 -alkoxy-, C 1 -C 6 -haloalkyl - or cyano-substrtuted C 3 -C 6 -cycloalkylcarbonyl, or a cation, or an optionally C 1 -C 6 -alkyl- Or aryl-C 1 -C 6 -alkyl-substituted ammonium ion,
R 7 is optionally halogen-, C 1 -C 6 -alkoxy-, C 1 -C 6 -haloalkoxy-,C 1 -C 6 -alkylthio-, C 1 -C 6 -haloalkylthio-, C 1 -C 6 -alkylsulphinyl-, C 1 -C 6 -haloalkylsulphinyl-, C 1 -C 6 -alkylsulphonyl- or C 1 -C 6 -haloalkylsulphonyl-substituted C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, optionally halogen-, C 1 -C 6 -alkyl-, C 1 -C 6 -haloalkyl-, C 1 -C 6 -alkoxy- or C 1 -C 6 -haloalkoxy-substituted C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, in which the rings optionally contain at least one heteroatom from the group of sulphur, oxygen (where, oxygen atoms must not be immediately adjacent) and nitrogen, optionally halogen-, cyano- (including in the alkyl moiety), nitro-, C 1 -C 6 -alkyl-, C 1 -C 6 -haloalkyl-, C 3 -C 6 -cycloalkyl-, C 1 -C 6 -alkoxy-, C 1 -C 6 -haloalkoxy-, C 1 -C 6 -alkylthio-, C 1 -C 6 -haloalkylthio-, C 1 -C 6 -alkylsulphinyl-, C 1 -C 6 -haloalkylsulphinyl-, C 1 -C 6 -alkylsulphonyl-, C 1 -C 6 -haloalkylsulphonyl-, amino-, C 1 -C 6 -alkylamino-, di(C 1 -C 6 -alkyl)amino-, C 1 -C 6 -alkylcarbonylamino-, C 1 -C 6 -alkoxycarbonylamino-, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl-, C 1 -C 6 -haloalkoxy-C 1 -C 6 -alkyl-, C 2 -C 6 -alkenyl-, C 2 -C 6 -alkynyl-, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl-,C 1 -C 6 -alkylcarbonyl-, C 1 -C 6 -alkoxycarbonyl- or aminocarbonyl-substituted aryl, heteroaryl, aryl-C 1 -C 6 -alkyl, heteroaryl-C 1 -C 6 -alkyl, or NR′R″ in which R′ and R″ are each independently a radical from the group 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 -alkoxylcarbonyl, or
R 2 and R 7 , together with the N—S(O) n group to which they are bonded, form a saturated or unsaturated and optionally halogen-, C 1 -C 6 -alkyl-, C 1 -C 6 -haloalkyl-, C 1 -C 6 -alkoxy-, C 1 -C 6 -haloalkoxy-substituted 5- to 7-membered ring which optionally contain one or more further heteroatoms from the group of sulphur, oxygen (where oxygen atoms must not be immediately adjacent) and nitrogen, and optionally contain at least one carbonyl group, or
R 2 and R 7 optionally together with the N—S(O) n group to which they are bonded, is a radical from the group of
in which the arrow in each case marks the bond to the C(X) group.
22. A compound of formula (I), a salt thereof, or an N-oxide thereof, of claim 1 , in which
A 1 is hydrogen, halogen or cyano,
A 2 is hydrogen,
R 1 is hydrogen or C 1 -C 4 -alkyl,
B is hydrogen,
X is oxygen,
n is 2,
R 2 is hydrogen, C 1 -C 4 -alkyl and 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, optionally halogen-, C 1 -C 4 -alkyl-, C 1 -C 4 -alkoxy-, C 1 -C 4 -haloalkyl- or cyano-substituted C 3 -C 6 -cycloalkylcarbonyl, or a cation, or an optionally C 1 -C 4 -alkyl- or aryl-C 1 -C 4 -alkyl-substituted ammonium ion, and
R 7 is optionally halogen-, C 1 -C 4 -alkoxy-, C 1 -C 4 -haloalkoxy-, C 1 -C 4 -alkylthio-, C 1 -C 4 -haloalkylthio-, C 1 -C 4 -alkylsulphinyl-, C 1 -C 4 -haloalkylsulphinyl-, C 1 -C 4 -alkylsulphonyl- or C 1 -C 4 -haloalkylsulphonyl-substituted C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, optionally halogen-, C 1 -C 4 -alkyl-, C 1 -C 4 -haloalkyl-, C 1 -C 4 -alkoxy-, C 1 -C 4 -haloalkoxy-substitated C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl and C 3 -C 4 -cycloalkenyl, in which the rings optionally contain at least one heteroatom from the group of sulphur, oxygen (where oxygen atoms must not be immediately adjacent) and nitrogen, optionally halogen-, cyano- (including in the alkyl moiety), nitro-, C 1 -C 4 -alkyl-, C 1 -C 4 -haloalkyl-, C 3 -C 6 -cycloalkyl-, C 1 -C 4 -alkoxy-, C 1 -C 4 -haloalkoxy-, C 1 -C 4 -alkylthio-, C 1 -C 4 -haloalkylthio-, C 1 -C 4 -alkylsulphinyl-, C 1 -C 4 -haloalkylsulphinyl-, C 1 -C 4 -alkylsulphonyl-, C 1 -C 4 -haloalkylsulphonyl-, amino-, C 1 -C 4 -alkylamino-, di(C 1 -C 4 -alkyl)amino-, C 1 -C 4 -alkylcarbonylamino-, C 1 -C 4 -alkoxycarbonylamino-, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl-, C 1 -C 4 -haloalkoxy-C 1 -C 4 -alkyl-, C 2 -C 4 -alkenyl-, C 2 -C 4 -alkynyl-, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl-, C 1 -C 4 -alkylcarbonyl-, C 1 -C 4 -alkoxycarbonyl- or ammocarbonyl-substituted aryl, heteroaryl, aryl-C 1 -C 4 -alkyl and heteroaryl-C 1 -C 4 -alkyl, or NR′R″in which R′ and R″ are each hydrogen or C 1 -C 4 -alkyl.
23. A compound of formula (I), a salt thereof, or an N-oxide thereof, of claim 22 , in which
A 1 is hydrogen, fluorine or chlorine,
G 1 is N, C—H, C—F or C—Cl,
R 1 is hydrogen or methyl,
R 2 is hydrogen, methyl, ethyl, CH 2 OCH 3 , CH 2 OCH 2 CH 3 , COCH 3 , COCH 2 CH 3 , cyclopropyl, Na + , K + or + NMe 4 , and
R 7 is methyl, ethyl, i-propyl, CF 3 , CHF 2 , CH 2 F, CH 2 CF 3 , cyclopropyl, dimethylamino, diethylamino, phenyl, benzyl, or
where the arrow in each case marks the bond to the sulphur atom in the radical (E).