Claims for Patent: 8,383,659

Summary for Patent: 8,383,659

Title:	Isoxazoline derivatives as pesticides
Abstract:	Novel isoxazoline compounds and compositions containing the compounds are disclosed. The compounds have pesticidal properties and are suitable for use on non-human animals.
Inventor(s):	Steve Nanchen, Noëlle Gauvry, Thomas Goebel
Assignee:	Elanco Tiergesundheit AG
Application Number:	US13/133,678
Patent Claims:	1. A compound of formula including all geometric and stereoisomers, N-oxides, and salts thereof, wherein X, is S(O)m, O or NR5′ and X1 and X2 are each independently of the other CR3′ or N, n is an integer from 0 to 4; m is an integer from 0 to 2; B1, B2 and B3 are each independently selected from the group consisting of CR2′ and N; each R2′ is independently of the other H or R2; each R3′ is independently of the other H or R3; R1 is C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C4-C7-alkylcycloalkyl or C4-C7-cycloalkylalkyl, each unsubstituted or substituted with one or more substituents independently selected from R4; R4 is halogen, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkyl-sulfonyl, cyano or nitro; each R2 is independently halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, N-mono- or N,N-di-C1-C6-alkylamino, C1-C6 alkoxycarbonyl, cyano (—CN) or nitro (—NO2); each R3 is independently H, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkyl-sulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, amino, N-mono- or N,N-di-C1-C6-alkylamino, C1-C6-alkoxycarbonyl, cyano, nitro or unsubstituted or halogen-, C1-C6-alkyl-, C1-C6-haloalkyl-, C1-C6-alkoxy-, C1-C6-haloalkoxy-, amino-, cyano- or nitro-substituted phenyl, pyridyl or pyrimidyl; Z is halogen, a radical Q or a group —C(W)—NR5R6; Q is a 5- or 6-membered heterocyclic ring or a C6-C10-carbocyclic ring system or a 8-, 9- or 10-membered fused hetero-bicyclic ring system, each of them being unsubstituted or substituted with one or more substituents independently selected from halogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, cyano, nitro, amino, N-mono- or N,N-di-C1-C4-alkylamino, C1-C6-alkoxycarbonyl, sulfonamido, N-mono- or N,N, di-C1-C4-alkylsulfonamido, C1-C6-alkylcarbonylamino, N-mono- or N,N-di-C1-C6-alkylaminocarbonyl, C2-C6-alkanoyl, a group -(alk)-C(W′)NR5″R7, phenyl, benzyl, benzoyl, phenoxy, pyridyl, pyridyl-(alk)-, pyrimidyl and pyrimidyl-(alk)-, wherein the phenyl, benzyl, benzoyl, phenoxy, pyridyl and pyrimidyl are each unsubstituted or substituted by halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, cyano, nitro or amino; (alk) is straight-chain or branched C1-C6-alkylene, W and W′ are each independently of the other O or S, R5, R5′ and R5″ are each independently of the other H, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C4-C7-alkylcycloalkyl, C4-C7-cycloalkylalkyl, C1-C6-alkylcarbonyl or C1-C6-alkoxycarbonyl; R6 is H; Q′, wherein Q′ has independently the meaning of Q; or is C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C4-C7-alkylcycloalkyl or C4-C7-cycloalkylalkyl, each unsubstituted or substituted by halogen C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, cyano, nitro, amino, N-mono- or N,N-di-C1-C6-alkylamino, C3-C6-cycloalkylamino, C1-C6-alkoxycarbonyl, C2-C6-alkanoyl, C1-C6-alkylcarbonylamino, aminocarbonyl, N-mono- or N,N-di-C1-C6-alkylaminocarbonyl, a group —C(W′)NR5″R7 or a radical Q″, wherein Q″ independently has the meaning of Q; or R5 and R6 together with the N-atom to which they are attached, form a 3- to 7-membered ring which optionally contains a further heteroatom selected from the group consisting of N, S and O, and which ring is further unsubstituted or substituted by C1-C2-alkyl, C1-C2-alkyl, C1-C2-alkoxy, halogen, cyano or nitro; and R7 is C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C4-C7-alkylcycloalkyl or C4-C7-cycloalkylalkyl, which is each unsubstituted or substituted by halogen C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, cyano, nitro, amino, N-mono- or N,N-di-C1-C6-alkylamino, pyridyl, pyrimidyl or thiazolyl, or by pyridyl, pyrimidyl or thiazolyl being mono- or disubstituted by halogen, cyano, C1-C2-alkyl or C1-C2-haloalkyl. 2. A compound of formula (I) according to claim 1, wherein X is S(O)m, O or NR5′ and X1 and X2 are each independently of the other CR3′ or N, n is an integer from 0 to 4; m is an integer from 0 to 2; B1, B2 and B3 are each independently selected from the group consisting of CR2′ and N; each R2′ is independently of the other H or R2; each R3′ is independently of the other H or R3; R1 is C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C4-C7-alkylcycloalkyl or C4-C7-cycloalkylalkyl, each unsubstituted or substituted with one or more substituents independently selected from R4; R4 is halogen, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkyl-sulfonyl, cyano or nitro; each R2 is independently halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, N-mono- or N,N-di-C1-C6-alkylamino, C2-C6-alkoxycarbonyl, cyano (—CN) or nitro (—NO2); each R3 is independently H, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6 alkyl-sulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, amino, N-mono- or N,N-di-C1-C6-alkylamino, C2-C6-alkoxycarbonyl, cyano or nitro; Z is halogen, a radical Q or a group —C(W)—NR5R6; Q is a 5- or 6-membered heterocyclic ring, or a C6-C10-carbocyclic ring system or a 8-, 9- or 10-membered fused hetero-bicyclic ring system, each of them being unsubstituted or substituted with one or more substituents independently selected from halogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, cyano, nitro, amino, N-mono- or N,N-di-C1-C6-alkylamino, C1-C6-alkoxycarbonyl, sulfonamido, N-mono- or N,N, di-C1-C6-alkylsulfonamido, C1-C6-alkylcarbonylamino, N-mono- or N,N-di-C1-C6-alkylaminocarbonyl, C2-C6-alkanoyl and unsubstituted or halogen-, C1-C6-alkyl-, C1-C6-haloalkyl-, C1-C6-alkoxy-, C1-C6-haloalkoxy-, cyano- or nitro-substituted phenyl, benzyl, benzoyl or phenoxy; W is O or S, R5 and R5′ are each independently of the other H, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C4-C7-alkylcycloalkyl, C4-C7-cycloalkylalkyl, C2-C6-alkylcarbonyl or C2-C6-alkoxycarbonyl; R6 is H; Q′, wherein Q′ independently has the meaning of Q; or is C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C4-C7-alkylcycloalkyl or C4-C7-cycloalkylalkyl, each unsubstituted or substituted by halogen C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, cyano, nitro, amino, N-mono- or N,N-di-C1-C4-alkylamino, C3-C6-cycloalkylamino, C2-C6-alkoxycarbonyl, C2-C6-alkanoyl, C2-C6-alkylcarbonylamino, aminocarbonyl, N-mono- or N,N-di-C1C6-alkylaminocarbonyl or a radical Q″, wherein Q″ independently has the meaning of Q; or R5 and R6 together with the N-atom to which they are attached, form a 3- to 7-membered ring which optionally contains a further heteroatom selected from the group consisting of N, S and O, and which ring is further unsubstituted or substituted by C1-C2-alkyl, C1-C2-alkyl, C1-C2-alkoxy, halogen, cyano or nitro. 3. A compound according to claim 1, wherein B1, B2 and B3 are each CR2′. 4. A compound according to claim 1, wherein X is S(O)m, O or NR5′, one of X1 and X2 is CR3′ and the other one is N or independently CR3′, wherein R3′ is each independently H or C1-C2-alkyl, R5′ is H or C1-C2-alkyl, and m is an integer from 0 to 2. 5. A compound according to claim 1, wherein R1 is halo-C1-C3-alkyl. 6. A compound according to claim 5, wherein R1 is CF3. 7. A compound according to claim 1 of formula wherein R1, R2, X, X1, X2, Z and n are as defined in claim 1. 8. A compound of formula (Ia) according to claim 7, wherein n is an integer from 1 to 3, R1 is halogen-substituted C1-C3-alkyl, each R2 is independently selected from the group consisting of halogen, C1-C6-haloalkyl, C1-C6-haloalkoxy and cyano, X is S(O)m, O or NR5′, m is an integer from 0 to 2, R5′ is H or C1-C2-alkyl, one of X1 and X2 is CR3′ and the other one is N or independently CR3′, wherein R3′ is each independently H or C1-C2-alkyl, and Z is either (i) halogen, or (ii) a radical Q of formula wherein (R)r is 0 to 3 same or different substituents selected from the group consisting of halogen, C1-C2-alkyl, C1-C2-haloalkyl, C1-C2-alkoxy, C1-C2-haloalkoxy, C1-C2-haloalkylthio, -cyano, nitro, and C1-C4-alkoxycarbonyl, or is (iii) a group —C(O)—NR5R6, wherein R5 is H, C1-C2-alkyl, C2-C4-alkylcarbonyl or C2-C4-alkoxycarbonyl and R6 is C1-C4-alkyl which is substituted by halogen, cyano, nitro or a radical Q-34, Q-48, Q-49 or Q-50 above, wherein R and r are as defined. 9. A compound of formula (Ia) according to claim 7, wherein n is an integer from 1 to 3, R1 is CF3, each R2 is independently selected from the group consisting of halogen, C1-C6-haloalkyl, C1-C6 haloalkoxy and cyano, X is S(O)m, wherein m is an integer from 0 to 2, one of X1 and X2 is CR3′ and the other one is N or independently CR3′, wherein R3′ is each independently H or C1-C2-alkyl, and Z is either (ii) the radical wherein r is 0; or (iii) a group —C(O)—NR5R6, wherein R5 is H and R6 is C1-C4-alkyl which is substituted by halogen or by a radical wherein r is 0. 10. A compound according to claim 9, wherein m is 0. 11. A compound of formula (Ia) according to claim 7, wherein Z is a radical —C(O)—NR5R6, wherein R5 is H, R6 is a radical -(alk)-C(O)—NR5″R7, (alk) is methylene or 1,2-ethylene, R5″ is H, and R7 is C1-C6-alkyl, which is unsubstituted or substituted by halogen, cyano or pyridyl, or is C2-C4-alkynyl or C3-C4-cycloalkyl. 12. A compound according to claim 11, wherein (alk) is methylene. 13. A compound of formula (Ia) according to claim 7, wherein Z is a radical Q, Q is a radical of formula R is a radical -(alk)-C(O)—NHR7, (alk) is methylene or 1,2-ethylene, and R7 is C1-C6-alkyl, which is unsubstituted or substituted by halogen, cyano or pyridyl, or is C2-C4-alkynyl or C3-C4-cycloalkyl. 14. A compound according to claim 13, wherein (alk) is methylene. 15. A compound according to claim 1, wherein Z is a 5- or 6-membered heterocyclic ring having from 1 to 4 same or different heteroatoms selected from the group consisting of N, O and S, which is further unsubstituted or substituted by one or more substituents selected from the group consisting of C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, C1-C4-alkylsulfinyl, C1-C4-haloalkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-haloalkylsulfonyl, cyano, nitro, C1-C4-alkoxycarbonyl, sulfonamido, N-mono- or N,N-di-C1-C4-alkylcarbonylamino, C2-C3-alkanoyl and unsubstituted or halogen- or C1-C4-alkyl-substituted phenyl, benzyl, benzoyl and phenoxy. 16. A compound according to claim 15, wherein Z is a radical Q of formula wherein (R)r is 0 to 3 same or different substituents selected from the group consisting of halogen, C1-C2-alkyl, C1-C2-haloalkyl, C1-C2-alkoxy, C1-C2-haloalkoxy, C1-C2-haloalkylthio, cyano, nitro, and C1-C4-alkoxycarbonyl. 17. A compound according to claim 16, wherein Z is the radical Q-34, wherein r is 0. 18. A compound according to claim 15, wherein Z is a 5- or 6-membered heterocyclic ring having from 1 to 3 same or different heteroatoms. 19. A compound according to claim 1, wherein Z is a group —C(O)—NR5R6, wherein R5 is H, C1-C2-alkyl, C2-C4-alkylcarbonyl or C2-C4-alkoxycarbonyl and R6 is C1-C4-alkyl which is substituted by halogen, cyano, nitro or a radical Q′ wherein Q″ is wherein (R)r is 0 to 3 same or different substituents selected from the group consisting of halogen, C1-C2-alkyl, C1-C2-haloalkyl, C1-C2-alkoxy, C1-C2-haloalkoxy, C1-C2-haloalkylthio, cyano, nitro, and C1-C4-alkoxycarbonyl. 20. A compound according to claim 19, wherein R5 is H and R6 is C1-C4-alkyl which is substituted by halogen or by a radical wherein r is 0. 21. A compound of formula (I) according to claim 1, wherein Z is a radical —C(W)—NR5R6, R6 is a radical -(alk)-C(W′)—NR5″R7, W and W′ are each independently O or S, (alk) is straight-chain or branched C1-C4-alkylene, and R5, R5″ and R7 are each as defined in claim 1. 22. A compound of formula (I) according to claim 1, wherein Z is a radical Q, Q is a radical of formula r is 1, R is a radical -(alk)—C(W′)—NR5″R7, (alk) is straight-chain or branched C1-C4-alkylene, W′ is O or S, and R5″ and R7 are each as defined in claim 1. 23. A compound of formula (I) according to claim 1, which is 5-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-3-methyl-thiophene-2-carboxylic acid [(2,2,2-trifluoro-ethylcarbamoyl)-methyl]-amide; or 5-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-3-methyl-thiophene-2-carboxylic acid (4-trifluoromethyl-thiazol-2-yl)-amide; or 5-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-3-methyl-thiophene-2-carboxylic acid ethylcarbamoylmethyl-amide; or 5-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-3-methyl-thiophene-2-carboxylic acid prop-2-ynylcarbamoylmethyl-amide; or 5-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-3-methyl-thiophene-2-carboxylic acid[(cyanomethyl-carbamoyl)-methyl]amide; or 5-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-3-methyl-thiophene-2-carboxylic acid [(2,2,2-trifluoro-ethylthiocarbamoyl)-methyl]amide; or 5-[5-(3,5-bis-trifluoromethyl-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-3-methyl-thiophene-2-carboxylic acid [(2,2,2-trifluoro-ethylcarbamoyl)-methyl]-amide; or 5-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-3-methyl-thiophene-2-carboxylic acid [(2,2,2-trifluoro-ethylcarbamoyl)-methyl]amide; or 5-[5-(3,5-dichloro-4-fluoro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-3-methyl-thiophene-2-carboxylic acid [(2,2,2-trifluoro-ethylcarbamoyl)-methyl]-amide. 24. Composition for the control of parasites, comprising as active ingredient at least one compound of the formula (I) according to claim 1, in addition to a carrier and/or a dispersant. 25. Method of controlling parasites in and on warm-blooded animals, which comprises applying to the animals a pharmaceutical effective amount of at least one compound of formula (I) according to claim 1.