Isoxazoline derivatives as pesticides

1. A topical formulation for controlling ectoparasites on a non-human animal comprising a carrier and/or a dispersing agent and a compound of formula

including all geometric and stereoisomers, N-oxides, and salts thereof, wherein

X, is S(O) m , O or NR 5 ′ and X 1 and X 2 are each independently of the other CR 3 ′ or N,

n is an integer from 0 to 4; m is an integer from 0 to 2;

B 1 , B 2 and B 3 are each independently selected from the group consisting of CR 2 ′ and N;

each R 2 ′ is independently of the other H or R 2 ;

each R 3 ′ is independently of the other H or R 3 ;

R 1 is C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 4 -C 7 -alkylcycloalkyl or C 4 -C 7 -cycloalkylalkyl, each unsubstituted or substituted with one or more substituents independently selected from R 4 ;

R 4 is halogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkyl-sulfonyl, cyano or nitro;

each R 2 is independently halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, N-mono- or N,N-di-C 1 -C 6 -alkylamino, C 1 -C 6 alkoxycarbonyl, cyano (—CN) or nitro (—NO 2 );

each R 3 is independently H, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkyl-sulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, amino, N-mono- or N,N-di-C 1 -C 6 -alkylamino, C 1 -C 6 -alkoxycarbonyl, cyano, nitro or unsubstituted or halogen-, C 1 -C 6 -alkyl-, C 1 -C 6 -haloalkyl-, C 1 -C 6 -alkoxy-, C 1 -C 6 -haloalkoxy-, amino-, cyano- or nitro-substituted phenyl, pyridyl or pyrimidyl;

Z is halogen, a radical Q or a group —C(W)—NR 5 R 6 ;

Q is a 5- or 6-membered heterocyclic ring or a C 6 -C 10 -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, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, cyano, nitro, amino, N-mono- or N,N-di-C 1 -C 4 -alkylamino, C 1 -C 6 -alkoxycarbonyl, sulfonamido, N-mono- or N,N, di-C 1 -C 4 -alkylsulfonamido, C 1 -C 6 -alkylcarbonylamino, N-mono- or N,N-di-C 1 -C 6 -alkylaminocarbonyl, C 2 -C 6 -alkanoyl, a group -(alk)-C(W′)NR 5 ″R 7 , 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, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, cyano, nitro or amino;

(alk) is straight-chain or branched C 1 -C 6 -alkylene,

W and W′ are each independently of the other O or S,

R 5 , R 5 ′ and R 5 ″ are each independently of the other H, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 4 -C 7 -alkylcycloalkyl, C 4 -C 7 -cycloalkylalkyl, C 1 -C 6 -alkylcarbonyl or C 1 -C 6 -alkoxycarbonyl;

R 6 is H; Q′, wherein Q′ has independently the meaning of Q; or is C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 4 -C 7 -alkylcycloalkyl or C 4 -C 7 -cycloalkylalkyl, each unsubstituted or substituted by halogen C 1 -C 6 -alkoxy, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, cyano, nitro, amino, N-mono- or N,N-di-C 1 -C 6 -alkylamino, C 3 -C 6 -cycloalkylamino, C 1 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkanoyl, C 1 -C 6 -alkylcarbonylamino, aminocarbonyl, N-mono- or N,N-di-C 1 C 6 -alkylaminocarbonyl, a group —C(W′)NR 5 ″R 7 or a radical Q″, wherein Q″ independently has the meaning of Q; or

R 5 and R 6 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 C 1 -C 2 -alkyl, C 1 -C 2 -alkyl, C 1 -C 2 -alkoxy, halogen, cyano or nitro; and

R 7 is C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 4 -C 7 -alkylcycloalkyl or C 4 -C 7 -cycloalkylalkyl, which is each unsubstituted or substituted by halogen C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, cyano, nitro, amino, N-mono- or N,N-di-C 1 -C 6 -alkylamino, pyridyl, pyrimidyl or thiazolyl, or by pyridyl, pyrimidyl or thiazolyl being mono- or disubstituted by halogen, cyano, C 1 -C 2 -alkyl or C 1 -C 2 -haloalkyl.

2. The topical formulation of claim 1 , wherein

X is S(O) m , O or NR 5 ′ and X 1 and X 2 are each independently of the other CR 3 ′ or N,

n is an integer from 0 to 4; m is an integer from 0 to 2;

B 1 , B 2 and B 3 are each independently selected from the group consisting of CR 2 ′ and N;

each R 2 ′ is independently of the other H or R 2 ;

each R 3 ′ is independently of the other H or R 3 ;

R 1 is C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 4 -C 7 -alkylcycloalkyl or C 4 -C 7 -cycloalkylalkyl, each unsubstituted or substituted with one or more substituents independently selected from R 4 ;

R 4 is halogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkyl-sulfonyl, cyano or nitro;

each R 2 is independently halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, N-mono- or N,N-di-C 1 -C 6 -alkylamino, C 2 -C 6 -alkoxycarbonyl, cyano (—CN) or nitro (—NO 2 );

each R 3 is independently H, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 alkyl-sulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, amino, N-mono- or N,N-di-C 1 -C 6 -alkylamino, C 2 -C 6 -alkoxycarbonyl, cyano or nitro;

Z is halogen, a radical Q or a group —C(W)—NR 5 R 6 ;

Q is a 5- or 6-membered heterocyclic ring, or a C 6 -C 10 -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, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, cyano, nitro, amino, N-mono- or N,N-di-C 1 -C 6 -alkylamino, C 1 -C 6 -alkoxycarbonyl, sulfonamido, N-mono- or N,N, di-C 1 -C 6 -alkylsulfonamido, C 1 -C 6 -alkylcarbonylamino, N-mono- or N,N-di-C 1 -C 6 -alkylaminocarbonyl, C 2 -C 6 -alkanoyl and unsubstituted or halogen-, C 1 -C 6 -alkyl-, C 1 -C 6 -haloalkyl-, C 1 -C 6 -alkoxy-, C 1 -C 6 -haloalkoxy-, cyano- or nitro-substituted phenyl, benzyl, benzoyl or phenoxy;

W is O or S,

R 5 and R 5 ′ are each independently of the other H, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 4 -C 7 -alkylcycloalkyl, C 4 -C 7 -cycloalkylalkyl, C 2 -C 6 -alkylcarbonyl or C 2 -C 6 -alkoxycarbonyl;

R 6 is H; Q′, wherein Q′ independently has the meaning of Q; or is C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 4 -C 7 -alkylcycloalkyl or C 4 -C 7 -cycloalkylalkyl, each unsubstituted or substituted by halogen C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, cyano, nitro, amino, N-mono- or N,N-di-C 1 -C 4 -alkylamino, C 3 -C 6 -cycloalkylamino, C 2 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkanoyl, C 2 -C 6 -alkylcarbonylamino, aminocarbonyl, N-mono- or N,N-di-C 1 C 6 -alkylaminocarbonyl or a radical Q″, wherein Q″ independently has the meaning of Q; or

R 5 and R 6 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 C 1 -C 2 -alkyl, C 1 -C 2 -alkyl, C 1 -C 2 -alkoxy, halogen, cyano or nitro.

3. The topical formulation of claim 1 , wherein the compound of formula I, B 1 , B 2 and B 3 are each CR 2 ′.

4. The topical formulation of claim 1 , wherein X is S(O) m , O or NR 5 ′, one of X 1 and X 2 is CR 3 ′ and the other one is N or independently CR 3 ′, wherein R 3 ′ is each independently H or C 1 -C 2 -alkyl, R 5 ′ is H or C 1 -C 2 -alkyl, and m is an integer from 0 to 2.

5. The topical formulation of claim 1 , wherein R 1 is halo-C 1 -C 3 -alkyl.

6. The topical formulation of claim 5 , wherein R 1 is CF 3 .

7. The topical formulation of claim 1 having formula Ia

wherein R 1 , R 2 , X, X 1 , X 2 , Z and n are as defined in claim 1 .

8. The topical formulation of claim 7 , wherein

n is an integer from 1 to 3, R 1 is halogen-substituted C 1 -C 3 -alkyl, each R 2 is independently selected from the group consisting of halogen, C 1 -C 6 -haloalkyl, C 1 -C 6 -haloalkoxy and cyano,

X is S(O) m , O or NR 5 ′, m is an integer from 0 to 2, R 5 ′ is H or C 1 -C 2 -alkyl, one of X 1 and X 2 is CR 3 ′ and the other one is N or independently CR 3 ′, wherein R 3 ′ is each independently H or C 1 -C 2 -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, C 1 -C 2 -alkyl, C 1 -C 2 -haloalkyl, C 1 -C 2 -alkoxy, C 1 -C 2 -haloalkoxy, C 1 -C 2 -haloalkylthio, -cyano, nitro, and C 1 -C 4 -alkoxycarbonyl, or is

(iii) a group —C(O)—NR 5 R 6 , wherein R 5 is H, C 1 -C 2 -alkyl, C 2 -C 4 -alkylcarbonyl or C 2 -C 4 -alkoxycarbonyl and R 6 is C 1 -C 4 -alkyl which is substituted by halogen, cyano, nitro or a radical Q-34, Q-48, Q-49 or Q-50 above.

9. The topical formulation of claim 7 , wherein n is an integer from 1 to 3, R 1 is CF 3 , each R 2 is independently selected from the group consisting of halogen, C 1 -C 6 -haloalkyl, C 1 -C 6 haloalkoxy and cyano, X is S(O) m , wherein m is an integer from 0 to 2, one of X 1 and X 2 is CR 3 ′ and the other one is N or independently CR 3 ′, wherein R 3 ′ is each independently H or C 1 -C 2 -alkyl, and Z is either

(ii) the radical

wherein r is 0; or

(iii) a group —C(O)—NR 5 R 6 , wherein R 5 is H and R 6 is C 1 -C 4 -alkyl which is substituted by halogen or by a radical

wherein r is 0.

10. The topical formulation of claim 9 , wherein m is 0.

11. The topical formulation of claim 7 , wherein Z is a radical —C(O)—NR 5 R 6 , wherein R 5 is H, R 6 is a radical -(alk)-C(O)—NR 5 ″R 7 , (alk) is methylene or 1,2-ethylene, R 5 ″ is H, and R 7 is C 1 -C 6 -alkyl, which is unsubstituted or substituted by halogen, cyano or pyridyl, or is C 2 -C 4 -alkynyl or C 3 -C 4 -cycloalkyl.

12. The topical formulation of claim 11 , wherein (alk) is methylene.

13. The topical formulation of claim 7 , wherein Z is a radical Q, Q is a radical of formula

R is a radical -(alk)-C(O)—NHR 7 , (alk) is methylene or 1,2-ethylene, and R 7 is C 1 -C 6 -alkyl, which is unsubstituted or substituted by halogen, cyano or pyridyl, or is C 2 -C 4 -alkynyl or C 3 -C 4 -cycloalkyl.

14. The topical formulation of claim 13 , wherein (alk) is methylene.

15. The topical formulation of 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 C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -haloalkylsulfonyl, cyano, nitro, C 1 -C 4 -alkoxycarbonyl, sulfonamido, N-mono- or N,N-di-C 1 -C 4 -alkylcarbonylamino, C 2 -C 3 -alkanoyl and unsubstituted or halogen- or C 1 -C 4 -alkyl-substituted phenyl, benzyl, benzoyl and phenoxy.

16. The topical formulation of 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, C 1 -C 2 -alkyl, C 1 -C 2 -haloalkyl, C 1 -C 2 -alkoxy, C 1 -C 2 -haloalkoxy, C 1 -C 2 -haloalkylthio, cyano, nitro, and C 1 -C 4 -alkoxycarbonyl.

17. The topical formulation of claim 16 , wherein Z is the radical Q-34, wherein r is 0.

18. The topical formulation of claim 15 , wherein Z is a 5- or 6-membered heterocyclic ring having from 1 to 3 same or different heteroatoms.

19. The topical formulation of claim 1 , wherein Z is a group —C(O)—NR 5 R 6 , wherein R 5 is H, C 1 -C 2 -alkyl, C 2 -C 4 -alkylcarbonyl or C 2 -C 4 -alkoxycarbonyl and R 6 is C 1 -C 4 -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. The topical formulation of 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. The topical formulation of claim 1 , wherein Z is a radical —C(W)—NR 5 R 6 , R 6 is a radical -(alk)-C(W′)—NR 5 ″R 7 , W and W′ are each independently O or S, (alk) is straight-chain or branched C 1 -C 4 -alkylene, and R 5 , R 5 ″ and R 7 are each as defined in claim 1 .

22. The topical formulation of claim 1 , wherein Z is a radical Q, Q is a radical of formula

r is 1, R is a radical -(alk)-C(W′)—NR 5 ″R 7 , (alk) is straight-chain or branched C 1 -C 4 -alkylene, W′ is O or S, and R 5 ″ and R 7 are each as defined in claim 1 .

23. The topical formulation of claim 1 , wherein the compound of formula I 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-d hydro-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. The topical formulation of claim 1 which is a spot-on, pour-on or spray-on formulation.

25. The topical formulation of claim 1 wherein the carrier is selected from oily solutions, alcoholic solutions, isopropanolic solutions, solutions of esters of monocarboxylic acids, and solutions of esters of aliphatic acids.

26. The topical formulation of claim 1 wherein the dispersing agent is selected from 2-pyrrolidone, 2-(N-alkyl)pyrrolidine, acetone, polyethylene glycol, ethers or esters of polyethylene glycol, propylene glycol and synthtic triglycerides.

27. The topical formulation of claim 25 wherein the oily solution is selected from the group consisting of vegetable oils, paraffins and silicone oils.

28. The topical formulation of claim 27 wherein the vegetable oil is olive oil, groundnut oil, sesame oil, pine oil, linseed oil or castor oil.

29. The topical formulation of claim 1 further comprising a stabiliser, anti-foaming agent, viscosity regulator, binding agent or tackifier.

30. A method of controlling ectoparasites on warm-blooded animals, which comprises topically applying to the animal, the topical formulation of claim 1 .