Anthranilamide derivatives as pesticides
View Patent ↗The present invention relates to novel anthranilamide derivatives of the general formula (I) in which R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , A, Q, Y and n are each as defined in the description—, to the use thereof as insecticides and acaricides for control of animal pests, and to several processes for preparation thereof.
1. An anthranilamide of the formula (I)
or an N-oxide and/or salt thereof,
in which
R 1 is hydrogen, methyl, cyclopropyl, cyanomethyl, methoxymethyl, methylthiomethyl, methylsulphinylmethyl or methylsulphonylmethyl,
R 2 is hydrogen or methyl,
R 3 is hydrogen; or is optionally singly or multiply, identically or differently substituted C 1 -C 6 -alkyl or C 1 -C 6 -alkoxy, where the substituents are each independently halogen, cyano, nitro, hydroxyl, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -alkylsulphimino, C 1 -C 4 -alkylsulphimino-C 1 -C 4 -alkyl, C 1 -C 4 -alkylsulphimino-C 2 -C 5 -alkylcarbonyl, C 1 -C 4 -alkylsulphoximino, C 1 -C 4 -alkyl sulphoximino-C 1 -C 4 -alkyl, C 1 -C 4 -alkyl sulphoximino-C 2 -C 5 -alkylcarbonyl, C 2 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkylcarbonyl or C 3 -C 6 -trialkylsilyl; or is optionally singly or multiply, identically or differently substituted C 3 -C 6 -cycloalkyl, where the substituents are each independently halogen, cyano, nitro, hydroxyl, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -alkylsulphimino, C 1 -C 4 -alkylsulphimino-C 1 -C 4 -alkyl, C 1 -C 4 -alkylsulphimino-C 2 -C 5 -alkylcarbonyl, C 1 -C 4 -alkylsulphoximino, C 1 -C 4 -alkylsulphoximino-C 1 -C 4 -alkyl, C 1 -C 4 -alkylsulphoximino-C 2 -C 5 -alkylcarbonyl, C 2 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkylcarbonyl, or C 3 -C 6 -trialkylsilyl,
Y is O or S,
R 4 is carboxyl, methoxymethyl, methylsulphonyloxy, methoxycarbonyl, hydroxyiminomethyl, hydroxyiminoethyl, acetyl, trifluoroacetyl, hydroxyethyl, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, aminothiocarbonyl, methylaminothiocarbonyl, dimethylaminothiocarbonyl, cyclopropylmethyloxycarbonyl, cyclobutylmethyloxycarbonyl, cyclobutyloxycarbonyl, 1,3-dioxane, dimethyl-1,3-dioxane, 1,3-dioxolane, trifluoromethylpyrazole or triazole,
n is 1 to 3,
R 5 is C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -haloalkyl, C 1 -C 6 -halocycloalkyl, C 2 -C 6 -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, fluorine, chlorine, bromine, iodine, cyano, nitro or C 3 -C 6 -trialkylsilyl,
R 6 is methyl or
R 7 is independently hydrogen, halogen or C 1 -C 4 -haloalkyl
m is 1 or 2,
X is N, CH, CF, CCl or CBr,
A is —CH 2 —, —CH(CH 3 ), C(CH 3 ) 2 or CH 2 CH 2 , and
Q is an optionally mono-substituted 5-membered aromatic heterocyclic ring Q-58 or Q-59 having the respective formulas
where the substituents are C 1 -C 3 -alkyl, C 1 -C 3 -haloalkyl, C 1 -C 2 -alkoxy, halogen, cyano, hydroxyl, nitro or C 1 -C 2 -haloalkoxy or are phenyl or a 5- or 6-membered heteroaromatic ring in which the phenyl or heteroaromatic ring is optionally mono- or polysubstituted identically or differently by C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkynyl, C 3 -C 6 -halocycloalkyl, halogen, CN, NO 2 , C 1 -C 4 -alkoxy, or C 1 -C 4 -haloalkoxy.
2. An anthranilamide according to claim 1 , wherein Y is O.
3. An anthranilamide according to claim 1 , wherein Y is S.
4. A process for preparing an anthranilamide according to claim 1 , in which Y is O, comprising
(A) reacting an aniline of formula (II)
with a carbonyl chloride of formula (III)
in the presence of an acid binder, or
(B) reacting an aniline of formula (II)
with a carboxylic acid of formula (IV)
in the presence of a condensing agent, or
(C) synthesizing an anthranilamide of formula (I) in which R 1 is hydrogen by reacting a benzoxazinone of formula (V)
with an amine of formula (XV)
in the presence of a diluent.
5. A composition comprising at least one anthranilamide according to claim 1 , and at least one further insecticide, fungicide, bactericide, acaricide, nematicide and/or a plant growth regulator.
6. An agrochemical composition comprising at least one anthranilamide according to claim 1 , and at least one extender and/or surfactant.
7. A process for producing an agrochemical composition, comprising mixing at least one anthranilamide according to claim 1 with at least one extender and/or surfactant.
8. An anthranilamide according to claim 1 adapted for control of animal pests.
9. A method for controlling animal pests, comprising allowing an anthranilamide according to claim 1 to act on animal pests and/or a habitat thereof and/or on seed.
10. A composition comprising at least one anthranilamide according to claim 2 , and at least one further insecticide, fungicide, bactericide, acaricide, nematicide and/or a plant growth regulator.
11. A composition comprising at least one anthranilamide according to claim 3 , and at least one further insecticide, fungicide, bactericide, acaricide, nematicide and/or a plant growth regulator.
12. A process for producing agrochemical compositions, comprising mixing a composition according to claim 5 with at least one extender and/or surfactant.
13. A method for controlling animal pests, comprising allowing a composition according to claim 5 to act on animal pests and/or a habitat thereof and/or on seed.
14. An agrochemical composition comprising at least one anthranilamide according to claim 2 , and at least one extender and/or surfactant.
15. An agrochemical composition comprising at least one anthranilamide according to claim 3 and at least one extender and/or surfactant.
16. A compound according to claim 1 , wherein R 1 and R 2 are hydrogen, R 3 is methyl, ethyl, isopropyl, tert-butyl, or cyanomethyl, Y is oxygen, and n is 1.
17. A compound according to claim 16 , wherein R 5 is methyl and R 6 is
18. A compound according to claim 16 , wherein R 5 is methyl and R 6 is
19. A compound according to claim 1 , wherein Q is Q-58.
20. One or more compounds according to claim 1 selected from the group consisting of
(a) a compound having the formula
(b) a compound having the formula
(c) a compound having the formula
(d) a compound having the formula
(e) a compound having the formula
(f) a compound having the formula
(g) a compound having the formula
(h) a compound having the formula
and
(i) a compound having the formula