Pesticidally active benzene- and azine-amide compounds
Compounds of formula (I) wherein the substituents are as defined in claim 1 , and the agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of those compounds, can be used as insecticides.
1 . A compound of the formula I
wherein:
Q is
A 1 , A 2 , A 3 and A 4 are independently CR 5 or N, provided not more than three of A 1 , A 2 , A 3 and A 4 are N;
R 1 is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 cyanoalkyl, aminocarbonylC 1 -C 6 alkyl, hydroxycarbonylC 1 -C 6 alkyl, C 1 -C 6 nitroalkyl, trimethylsilaneC 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl; C 3 -C 4 cycloalkylC 1 -C 2 alkyl- wherein the C 3 -C 4 cycloalkyl is optionally substituted with 1 or 2 halo atoms; oxetan-3-yl-CH 2 —; or benzyl optionally substituted with halo or C 1 -C 6 haloalkyl;
R 2 is phenyl, pyridine, pyrimidine, pyrazine or pyridazine, wherein the phenyl, pyridine, pyrimidine, pyrazine or pyridazine is optionally substituted with one to three substituents, provided the substituent(s) are not on either carbon adjacent to the carbon C═O is attached, and each substituent is independently selected from: C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 thiohaloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, halogen, NO 2 , SF 5 , CN, CONH 2 , COOH and C(S) NH 2 ;
R 3 is C 1 -C 3 alkyl or C 1 -C 3 haloalkyl;
R 4 is pyridine, pyrimidine, pyrazine or pyridazine, wherein the pyridine, pyrimidine, pyrazine or pyridazine is optionally substituted with one to three substituents, independently selected, from C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 3 -C 4 cycloalkyl, halogen or hydroxy;
R 5 is hydrogen, halogen, CN, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 3 -C 4 cycloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkoxycarbonyl, or di(C 1 -C 3 alkoxy) methane; with the proviso that R 4 is not pyridin-3-yl, if A 1 , A 2 , A 3 and A 4 are all CH; or a stereoisomer, enantiomer, tautomer and N-oxide of the compound of formula I, or agrochemically acceptable salt thereof.
2 . The compound according to claim 1 , wherein R 3 is methyl.
3 . The compound according to claim 1 , wherein R 1 is hydrogen; C 1 -C 6 alkyl optionally substituted with one substituent selected from: CN, CONH 2 , COOH, NO 2 , and —Si(CH 3 ) 3 ; C 1 -C 6 haloalkyl; C 2 -C 6 alkenyl; C 2 -C 6 alkynyl; C 2 -C 6 haloalkynyl; C 3 -C 4 cycloalkyl-C 1 -C 2 alkyl- wherein the C 3 -C 4 cycloalkyl- is optionally substituted with 1 or 2 halo atoms; oxetan-3-yl-CH 2 —; or benzyl optionally substituted with halo or C 1 -C 3 haloalkyl.
4 . The compound according to claim 1 , wherein R 2 is one of Z 1 to Z 10
5 . The compound according to claim 1 , wherein Q is selected from Q-1 to Q-12
wherein R 4 is pyridine, pyrimidine, pyrazine or pyridazine, wherein the pyridine, pyrimidine, pyrazine or pyridazine is optionally substituted with one to three substituents, independently selected, from C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 3 -C 4 cycloalkyl, halogen and hydroxyl.
6 . The compound according to claim 1 , wherein R 4 is 2-pyridine or 2-pyrimidine optionally substituted by a substituent from halogen and C 1 -C 3 alkoxy.
7 . The compound according to claim 1 , wherein R 1 is cyclopropyl-CH 2 —, CH≡CCH 2 —, hydrogen, or Me.
8 . The compound according to claim 2 , wherein R 2 is one of Z 1 to Z 10
9 . The compound according to claim 3 , wherein R 2 is one of Z 1 to Z 10
10 . The compound according to claim 2 , wherein Q is selected from Q-1 to Q-12
wherein R 4 is pyridine, pyrimidine, pyrazine or pyridazine, wherein the pyridine, pyrimidine, pyrazine or pyridazine is optionally substituted with one to three substituents, independently selected, from C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 3 -C 4 cycloalkyl, halogen or hydroxyl.
11 . The compound according to claim 3 , wherein Q is selected from Q-1 to Q-12
wherein R 4 is pyridine, pyrimidine, pyrazine or pyridazine, wherein the pyridine, pyrimidine, pyrazine or pyridazine is optionally substituted with one to three substituents, independently selected, from C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 3 -C 4 cycloalkyl, halogen or hydroxyl.
12 . The compound according to claim 4 , wherein Q is selected from Q-1 to Q-12
wherein R 4 is pyridine, pyrimidine, pyrazine or pyridazine, wherein the pyridine, pyrimidine, pyrazine or pyridazine is optionally substituted with one to three substituents, independently selected, from C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 3 -C 4 cycloalkyl, halogen or hydroxyl.
13 . A composition comprising a compound as defined in claim 1 , one or more auxiliaries and diluent, and optionally one more other active ingredient.
14 . A plant propagation material, comprising, or treated with or adhered thereto, a compound as defined in claim 1 .
15 . A method of combating and controlling insects, acarines, nematodes or molluscs which comprises applying to a pest, to a locus of a pest, or to a plant susceptible to attack by a pest an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound as defined in claim 1 .