IP Library Granted Patent US 9,247,740
Granted Patent B2
US 9,247,740 · App. 14/240,428 · Granted Feb 2, 2016

Isoxazoline derivatives as insecticidal compounds

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Quick Facts
Patent No.
US 9,247,740
App. No.
14/240,428
Granted
Feb 2, 2016
Kind
B2
Abstract

The present invention provides compounds of formula (I), wherein G 1 is oxygen; R 1 is hydrogen; R 2 is group P (P) L is a bond, methylene or ethylene; one of A 1 and A 2 is S, SO or SO 2 and the other is —C(R 4 )R 4 —R 3 is hydrogen or methyl; each R 4 is independently hydrogen or methyl; Y 1 is C—R 6 , CH or nitrogen; Y 2 and Y 3 are independently CH or nitrogen; wherein no more than two of Y 1 , Y 2 and Y 3 are nitrogen and wherein Y 2 and Y 3 are not both nitrogen; R 5 is hydrogen, halogen, cyano, nitro, NH 2 , C 1 -C 2 alkyl, C 1 -C 2 haloalkyl, C 3 -C 5 cycloalkyl, C 3 -C 5 halocycloalkyl, C 1 -C 2 alkoxy, C 1 -C 2 haloalkoxy; R 6 together with R 5 forms a —CH═CH—CH═CH— bridge; X 2 is C—X 6 or nitrogen; X 1 , X 3 and X 6 are independently hydrogen, halogen or trihalomethyl, wherein at least two of X 1 , X 3 and X 6 are not hydrogen; X 4 is trifluoromethyl, difluoromethyl or chlorodifluoromethyl. The invention also provides intermediates useful for the preparation of compounds of formula (I), as well as methods of controlling insects, acarines, nematodes or molluscs using the compounds of formula (I).

Claims (41)

1. A compound of formula I

wherein

G 1 is oxygen;

R 1 is hydrogen;

R 2 is group P

L is a bond, methylene or ethylene;

one of A 1 and A 2 is S, SO or SO 2 and the other is —C(R 4 )R 4 —;

R 3 is hydrogen or methyl;

each R 4 is independently hydrogen or methyl;

Y 1 , Y 2 and Y 3 are independently CH or nitrogen;

wherein no more than two of Y 1 , Y 2 and Y 3 are nitrogen and wherein Y 2 and Y 3 are not both nitrogen;

R 5 is hydrogen, halogen, cyano, nitro, NH 2 , C 1 -C 2 alkyl, C 1 -C 2 haloalkyl, C 3 -C 5 cycloalkyl, C 1 -C 2 halocycloalkyl, C 1 -C 2 alkoxy, C 1 -C 2 haloalkoxy;

X 2 is C—X 6 or nitrogen;

X 1 , X 3 and X 6 are independently halogen or trihalomethyl; and

X 4 is trifluoromethyl, difluoromethyl or chlorodifluoromethyl.

2. A compound according to claim 1 , wherein R 2 is thietan-3-yl-, 1-oxo-thietan-3-yl-, 1,1-Dioxo-thietan-3-yl-, 2,2-dimethylthietan-3-yl-, 2,2-dimethyl-1-oxo-thietan-3-yl-, 2,2-dimethyl-1,1-Dioxo-thietan-3-yl-, 3-Methyl-thietan-3-yl-, 3-Methyl-1-oxo-thietan-3-yl-, 3-Methyl-1,1-Dioxo-thietan-3-yl-, thietan-3-ylmethyl-, 1-oxo-thietan-3-ylmethyl-, 1,1-Dioxo-thietan-3-ylmethyl-, thietan-2-ylmethyl-, (1-oxothietan-2-yl)methyl-, (1,1-dioxothietan-2-yl)methyl-, 2-(thietan-3-yl)ethanyl, 2-(1,1-dioxothietan-3-yl)ethanyl, or 2-(1-oxothietan-3-yl)ethanyl.

3. A compound according to claim 1 , wherein

Y 1 is CH, Y 2 is CH, Y 3 is CH, or

Y 1 is N, Y 2 is CH, Y 3 is CH, or

Y 1 is N, Y 2 is N, Y 3 is CH, or

Y 1 is CH, Y 2 is N, Y 3 is CH, or

Y 1 is CH, Y 2 is CH, Y 3 is N.

4. A compound according to claim 1 , wherein R 5 is hydrogen, chloro, bromo, fluoro, trifluoromethyl, methyl, ethyl, methoxy, nitro, trifluoromethoxy, cyano, or cyclopropyl.

5. A compound according to claim 1 , wherein

X 1 is chloro, X 2 is CH, X 3 is chloro, or

X 1 is chloro, X 2 is C—Br, X 3 is chloro, or

X 1 is chloro, X 2 is C—F, X 3 is chloro, or

X 1 is chloro, X 2 is C—Cl, X 3 is chloro, or

X 1 is chloro, X 2 is C—I, X 3 is chloro, or

X 1 is fluoro, X 2 is C—F, X 3 is fluoro, or

X 1 is chloro, X 2 is C—Cl, X 3 is trifluoromethyl, or

X 1 is trifluoromethyl, X 2 is C—Cl, X 3 is trifluoromethyl, or

X 1 is chloro, X 2 is N, X 3 is chloro, or

X 1 is trifluoromethyl, X 2 is N, X 3 is trifluoromethyl.

6. A compound according to claim 1 , wherein X 2 is C—X 6 , Y 1 , Y 2 and Y 3 are C—H, R 3 is hydrogen and each R 4 is hydrogen.

7. A method of 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 of formula (I) as defined in claim 1 .

8. An insecticidal, acaricidal, nematicidal or molluscicidal composition comprising an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (I) as defined in claim 1 .

9. An insecticidal, acaricidal, nematicidal or molluscicidal composition according to claim 8 comprising at least one additional compound having biological activity.

10. 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, wherein the combination product is for use in a method of therapeutic treatment.

11. 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 , wherein component B is enrofloxacin, praziquantel, pyrantel embonate, febantel, penethamate, moloxicam, cefalexin, kanamycin, pimobendan, clenbuterol, omeprazole, tiamulin, benazepril, pyriprole, cefquinome, florfenicol, buserelin, cefovecin, tulathromycin, ceftiour, selamectin, carprofen, moxidectin, clorsulon, pyrantel, eprinomectin, doramectin, selamectin, nemadectin, albendazole, cambendazole, fenbendazole, flubendazole, mebendazole, oxfendazole, oxibendazole, parbendazole, tetramisole, levamisole, pyrantel pamoate, oxantel, morantel, triclabendazole, epsiprantel, lufenuron or ecdysone.

12. A combination product according to claim 10 , wherein component B is enrofloxacin, praziquantel, pyrantel embonate, febantel, penethamate, moloxicam, cefalexin, kanamycin, pimobendan, clenbuterol, omeprazole, tiamulin, benazepril, pyriprole, cefquinome, florfenicol, buserelin, cefovecin, tulathromycin, ceftiour, selamectin, carprofen, moxidectin, clorsulon or pyrantel.

Assignments (2)
MERGER AND CHANGE OF NAME Recorded Mar 14, 2025
From: SYNGENTA PARTICIPATIONS AG; SYNGENTA PARTICIPATIONS AG
To: SYNGENTA CROP PROTECTION AG
Reel/Frame 070517/0654 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 15, 2015
From: CASSAYRE, JEROME YVES; RENOLD, PETER; PITTERNA, THOMAS; EL QACEMI, MYRIEM
To: SYNGENTA PARTICIPATIONS AG
Reel/Frame 034770/0703 →