Insecticidal compounds
The present invention provides compounds 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; B 1 -B 2 -B 3 -B 4 is —CH 2 —C═N—CH 2 —, —CH 2 —N—CH 2 —CH 2 —, —CH 2 —C═CH—O— or —CH═C—CH 2 —O—; 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 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 1 -C 8 alkoxy-C 1 -C 8 alkyl, aryl or aryl substituted by one to three R 6 , or R 1 is heterocyclyl or heterocyclyl substituted by one to three R 6 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 ; Y 1 is CR 7 R 8 , C—O or C═S; Y 2 , Y 3 and Y 4 are independently CR 7 R 8 , C═O, C═S, N—R 9 , O, S, SO or SO 2 ; wherein at least two adjacent ring atoms in the ring formed by Y 1 , Y 2 , Y 3 and Y 4 are heteroatoms; each R 7 and R 8 is independently hydrogen, halogen, C 1 -C 8 alkyl, or C 1 -C 8 haloalkyl; and R 5 , R 6 , R 7 , R 8 and R 9 are as defined in the claims. The invention also relates to processes and intermediates for preparing these compounds, to insecticidal, acaricidal, nematicidal and molluscicidal compositions comprising these compounds and to methods of using these compounds to control insect, acarine, nematode and mollusc pests.
1. A compound of formula (I)
wherein
A 2 , A 3 , and A 4 are independently C—H or N, wherein no more than one of A 2 , A 3 , and A 4 is N;
B 1 -B 2 -B 3 -B 4 is —CH 2 —C═N—CH 2 — or —CH 2 —N—CH 2 —CH 2 —;
R 5 is hydrogen, halogen, C 1 -C 4 alkyl, C 3 -C 4 cycloalkyl, C 2 -C 4 alkenyl or C 1 -C 4 haloalkyl;
each R 6 is independently hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, or C 1 -C 4 haloalkoxy;
Y 1 is C═O, Y 2 is N—R 9 , Y 3 is O, and Y 4 is CH 2 ; or
Y 1 is CH 2 , Y 2 is S═O, Y 3 is O, and Y 4 is CH 2 ; and
each R 9 is independently hydrogen, cyano, cyano-C 1 -C 4 alkyl, C 1 -C 4 alkyl, C 1 -C 4 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 4 alkyl, C 3 -C 8 cycloalkyl-C 1 -C 4 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 4 haloalkyl, C 1 -C 4 hydroxyalkyl, C 1 -C 4 alkoxy-C 1 -C 4 alkyl, C 2 -C 6 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 2 -C 4 haloalkynyl, phenyl, phenyl substituted by one to three R 10 , heteroaryl, heteroaryl 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 , heteroaryl-C 1 -C 4 alkyl or 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 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, or C 1 -C 4 haloalkoxy, or a salt or N-oxide thereof.
2. The compound according to claim 1 , wherein B 1 -B 2 -B 3 -B 4 is —CH 2 —C═N—CH 2 —.
3. The compound according to claim 1 , wherein B 1 -B 2 -B 3 -B 4 is —CH 2 —N—CH 2 —CH 2 —.
4. The compound according to claim 1 , wherein each R 5 independently is bromo, chloro, fluoro, cyclopropyl, trifluoromethyl, vinyl, or methyl.
5. The compound according to claim 1 , wherein each R 9 is independently hydrogen, cyano-C 1 -C 4 alkyl, C 1 -C 4 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 4 haloalkyl, C 1 -C 4 hydroxyalkyl, C 2 -C 4 alkenyl, C 2 -C 4 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.
6. The compound according to claim 1 , wherein each R 9 is independently hydrogen, C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 haloalkyl, C 1 -C 4 hydroxyalkyl, C 1 -C 4 alkoxy-C 1 -C 4 alkyl, phenyl- 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.
7. 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 .
8. 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.
9. 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 component 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.
10. The compound of claim 1 , wherein the compound of formula (I) is selected from:
11. The compound of claim 1 , wherein the compound of formula (I) is selected from:
12. A compound of formula (I)
wherein
A 2 , A 3 , and A 4 are independently C—H or N, wherein no more than one of A 2 , A 3 , and A 4 is N;
B 1 -B 2 -B 3 -B 4 is —CH 2 —C═CH—O— or —CH═C—CH 2 —O—;
R 5 is hydrogen, halogen, nitro, C 1 -C 4 alkyl, C 3 -C 4 cycloalkyl, C 2 -C 4 alkenyl or C 1 -C 4 haloalkyl;
each R 6 is independently hydrogen, halogen, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, or C 1 -C 4 haloalkoxy;
Y 1 is C═O, Y 2 is N—R 9 , Y 3 is O, and Y 4 is CH 2 ; or
Y 1 is CH 2 , Y 2 is S═O, Y 3 is O, and Y 4 is CH 2 ; and
each R 9 is independently hydrogen, cyano, cyano-C 1 -C 4 alkyl, C 1 -C 4 alkyl, C 1 -C 4 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 4 alkyl, C 3 -C 8 cycloalkyl-C 1 -C 4 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 4 haloalkyl, C 1 -C 4 hydroxyalkyl, C 1 -C 4 alkoxy-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, phenyl, phenyl substituted by one to three R 10 , heteroaryl, heteroaryl 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 , heteroaryl-C 1 -C 4 alkyl or 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 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, or C 1 -C 4 haloalkoxy, or a salt or N-oxide thereof providing that Y 1 -Y 2 -Y 3 -Y 4 is not —CH 2 —O—N(R a )—C(═O)—, wherein R a is hydrogen, methyl, ethyl, propyl, isopropyl, butyl, cyclopropyl, cyclopropyl-methyl, cyclobutyl, cyclobutyl-methyl, oxetanyl, thietanyl, trifluoroethyl, difluoroethyl, allyl, propargyl, cyanomethyl, benzyl, benzyl substituted by one to three R b , or R a is pyridyl-methyl- or pyridyl-methyl-substituted by one to three R b ; and each R b is independently fluoro, chloro, bromo, trifluoromethyl, trifluoromethoxy, cyano or methoxy.
13. The compound according to claim 12 , wherein B 1 -B 2 -B 3 -B 4 is —CH 2 —C═CH—O—.
14. The compound according to claim 13 , wherein B 1 -B 2 -B 3 -B 4 is —CH═C—CH 2 —O—.
15. The compound according to claim 12 , wherein each R 5 independently is bromo, chloro, fluoro, cyclopropyl, trifluoromethyl, vinyl, or methyl.
16. The compound according to claim 12 , wherein each R 9 is independently hydrogen, cyano-C 1 -C 4 alkyl, C 1 -C 4 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 4 haloalkyl, C 1 -C 4 hydroxyalkyl, C 2 -C 4 alkenyl, C 2 -C 4 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.
17. The compound according to claim 12 , wherein each R 9 is independently hydrogen, C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 haloalkyl, C 1 -C 4 hydroxyalkyl, C 1 -C 4 alkoxy-C 1 -C 4 alkyl, phenyl- 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.
18. 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 12 .
19. A composition comprising a pesticidally effective amount of a compound of formula (I) as defined in claim 12 optionally comprising an additional pesticidally active ingredient.
20. 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 12 , and component 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.
21. The compound of claim 12 , wherein the compound of formula (I) is selected from: