Insecticidal compounds based on isoxazoline derivatives

1. A compound of formula (I):

wherein

A 1 , A 2 , A 3 and A 4 are independently of one another C—H, C—R 5 , or nitrogen;

G 1 is oxygen or sulfur;

L is a single bond or C 1 -C 8 alkylene;

R 1 is hydrogen, C 1 -C 8 alkyl, C 1 -C 8 alkylcarbonyl-, C 1 -C 8 alkoxy, C 1 -C 8 alkoxy-C 1 -C 8 alkyl, or C 1 -C 8 alkoxycarbonyl-;

R 2 is hydrogen, C 1 -C 8 haloalkyl or C 1 -C 8 alkyl;

R 3 is C 1 -C 8 haloalkyl;

R 4 is aryl or aryl substituted by one to three R 6 , or R 4 is heterocyclyl or heterocyclyl substituted by one to three R 6 ;

each R 5 is independently halogen, cyano, nitro, C 1 -C 8 alkyl, C 3 -C 8 cycloalkyl, C 1 -C 8 haloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 haloalkenyl, C 2 -C 8 alkynyl, C 2 -C 8 haloalkynyl, C 1 -C 8 alkoxy, C 1 -C 8 haloalkoxy, C 1 -C 8 alkoxycarbonyl-, or two R 5 on adjacent carbon atoms together form a —CH═CH—CH═CH— bridge or a —N═CH—CH═CH— bridge;

each R 6 is independently halogen, cyano, nitro, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 1 -C 8 alkoxy, or C 1 -C 8 -haloalkoxy;

Y 1 is CR 7 R 8 is O, Y 3 is N-R 9 and Y 4 is C═O;

each R 7 and R 8 is independently hydrogen, halogen, C 1 -C 8 alkyl, or C 1 -C 8 haloalkyl;

each R 9 is independently hydrogen, cyano, cyano-C 1 -C 8 alkyl, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkyl where one carbon atom is replaced by O, S, S(O) or SO 2 , or C 3 -C 8 cycloalkyl-C 1 -C 8 alkyl, C 3 -C 8 cycloalkyl-C 1 -C 8 alkyl where one carbon atom in the cycloalkyl group is replaced by O, S, S(O) or SO 2 , or C 3 -C 8 cycloalkyl-C 1 -C 8 haloalkyl, C 1 -C 8 hydroxyalkyl, C 1 -C 8 alkoxy-C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 haloalkenyl, C 2 -C 8 alkynyl, C 2 -C 8 haloalkynyl, phenyl, phenyl substituted by one to three R 10 , phenyl-C 1 -C 4 alkyl, phenyl-C 1 -C 4 alkyl wherein the phenyl moiety is substituted by one to three R 10 , 5-6 membered heteroaryl-C 1 -C 4 alkyl or 5-6 membered heteroaryl-C 1 -C 4 alkyl wherein the heteroaryl moiety is substituted by one to three R 10 , or C 1 -C 4 alkyl-(C 1 -C 4 alkyl-O—N═)C—CH 2 —;

each R 10 is independently halogen, cyano, nitro, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 1 -C 8 alkoxy, or C 1 -C 8 haloalkoxy;

or a salt or N-oxide thereof.

2. A compound according to claim 1 , wherein the compound is a compound of formula (Ia.E):

3. A compound according to claim 1 , wherein R 9 is hydrogen, cyano-C 1 -C 8 alkyl, C 1 -C 8 alkyl, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkyl where one carbon atom in the cycloalkyl group is replaced by O, S, S(O) or SO 2 , or C 1 -C 8 haloalkyl, C 1 -C 8 hydroxyalkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, phenyl-C 1 -C 4 alkyl or phenyl-C 1 -C 4 alkyl wherein the phenyl moiety is substituted by one to three R 10 , 5-6 membered heteroaryl-C 1 -C 4 alkyl or 5-6 membered heteroaryl-C 1 -C 4 alkyl wherein the heteroaryl moiety is substituted by one to three R 10 , and wherein the heteroaryl is pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, pyrazolyl, furanyl, thiophenyl, oxazolyl, isoxazolyl or thiazolyl.

4. A method of combating and/or controlling an invertebrate animal pest which comprises applying to the pest, to a locus of the pest, or to a plant susceptible to attack by the pest a pesticidally effective amount of a compound of formula (I) as defined in claim 1 .

5. A composition comprising a pesticidally effective amount of a compound of formula (I) as defined in claim 1 optionally comprising an additional pesticidally active ingredient.

6. A combination product comprising a pesticidally effective amount of a component A and a pesticidally effective amount of component B, wherein component A is a compound of formula (I) as defined in claim 1 , and compound B is imidacloprid, enrofloxacin, praziquantel, pyrantel embonate, febantel, penethamate, moloxicam, cefalexin, kanamycin, pimobendan, clenbuterol, fipronil, ivermectin, omeprazole, tiamulin, benazepril, milbemycin, cyromazine, thiamethoxam, pyriprole, deltamethrin, cefquinome, florfenicol, buserelin, cefovecin, tulathromycin, ceftiour, selamectin, carprofen, metaflumizone, moxidectin, methoprene (including S-methoprene), clorsulon, pyrantel, amitraz, triclabendazole, avermectin, abamectin, emamectin, eprinomectin, doramectin, selamectin, nemadectin, albendazole, cambendazole, fenbendazole, flubendazole, mebendazole, oxfendazole, oxibendazole, parbendazole, tetramisole, levamisole, pyrantel pamoate, oxantel, morantel, triclabendazole, epsiprantel, fipronil, lufenuron, ecdysone or tebufenozide.

7. A compound according to claim 1 , wherein A 1 is C—R 5 , A 2 is C—H, A 3 is C—H, A 4 is C—H.

8. A compound according to claim 1 , wherein R 3 is chlorodifluoromethyl or trifluoromethyl.

9. A compound according to claim 1 , wherein R 4 is phenyl substituted by one to three R 6 .

10. A compound according to claim 1 , wherein R 5 is bromo, chloro, fluoro, cyclopropyl, vinyl, or methyl.

11. A compound according to claim 1 , wherein each R 6 is independently chloro, fluoro, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxy, or trifluoromethoxy.

12. A compound according to claim 1 , wherein R 9 is hydrogen, C 1 -C 4 alkyl, C 3 -C 6 cyclo alkyl, C 1 -C 4 halo alkyl, C 1 -C 4 hydroxyalkyl, C 1 -C 4 alkoxy-C 1 -C 4 alkyl, phenyl-CH 2 -alkyl- or phenyl-CH 2 — wherein the phenyl moiety is substituted by one to three R 10 , furanyl or furanyl substituted by one to three R 10 , thietanyl, oxetanyl, oxo-thietanyl, or dioxo-thietanyl.

13. A compound according to claim 1 , wherein R 9 is methyl, ethyl, cyclopropyl, cyclobutyl, oxetanyl, thietanyl, trifluoroethyl, difluoroethyl, allyl, propargyl, cyanomethyl, benzyl, benzyl substituted by one to three R 10 , or pyridine-methyl- or pyridine-methyl-substituted by one to three R 10 .

14. A compound according to claim 1 , wherein R 9 is ethyl or trifluoroethyl.

15. A compound according to claim 2 , wherein

A l is C-R 5 , A 2 is C-H, A 3 is C-H, A 4 is C-H;

R 3 is chlorodifluoromethyl or trifluoromethyl;

R 4 is phenyl substituted by one to three R 6 ;

R 5 is bromo, chloro, fluoro, cyclopropyl, vinyl, or methyl;

each R 6 is independently chloro, fluoro, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxy, or trifluoromethoxy;

R 9 is ethyl or trifluoroethyl.