Isoxazole derivatives

1. A compound of formula

including all geometric and stereoisomers, N-oxides, S-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,

m is an integer from 0 to 2;

R 5 ′ is H, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylcarbonyl or C 1 -C 6 -alkoxycarbonyl;

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;

B and B′ are each independently a group CR 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 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 );

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, hydroxy, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, cyano or nitro;

R 5 is H, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, halogen or cyano; or R 5 and X 2 together with the intermediate C-atoms form a 5- or 6-membered carbocyclic ring; or R 5 and X 1 together with the intermediate C-atoms form a 5- or 6-membered carbocyclic ring;

R 6 is H; C 1 -C 6 -alkyl, which is unsubstituted or substituted by C 1 -C 4 -alkoxy, cyano, phenyl, ethenyl or ethynyl; C 2 -C 7 -alkylcarbonyl; C 2 -C 7 -haloalkylcarbonyl; or C 2 -C 7 -alkoxycarbonyl;

Z is C 1 -C 6 -alkyl, a group —C(O)-Q, a group —C(S)-Q or a group —S(O) t -Q; t is 1 or 2;

Q is C 1 -C 6 -alkoxy; C 1 -C 6 -haloalkoxy; C 1 -C 6 -alkylthio; C 1 -C 6 -haloalkylthio; NR 7 R 8 ;

C(O)OR 7 ; C(O)R 7 ; C 1 -C 6 -alkyl which is unsubstituted or substituted by C 3 -C 6 -cycloalkyl, halogen, cyano, nitro, hydroxy, 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, NHC(O)R 7 , C 1 -C 6 -alkoxycarbonyl, sulfonamido, N-mono- or N,N, di-C 1 -C 4 -alkylsulfonamido, C(O)NR 7 R 8 , C 2 -C 6 -alkanoyl, unsubstituted or C 1 -C 2 -alkyl-, C 1 -C 2 -haloalkyl-, C 1 -C 2 -alkoxy-, C 1 -C 2 -haloalkoxy-, halogen-, cyano- or C 1 -C 4 -alkoxycarbonyl-substituted C 6 -C 10 -aryl, or unsubstituted or C 1 -C 2 -alkyl-, C 1 -C 2 -haloalkyl-, C 1 -C 2 -alkoxy-, C 1 -C 2 -haloalkoxy-, halogen-, cyano- or C 1 -C 4 -alkoxycarbonyl-substituted 4- to 6-membered heterocyclyl; C 2 -C 6 -alkenyl; C 2 -C 6 -alkynyl; C 3 -C 6 -cycloalkyl which is unsubstituted or substituted by halogen, C 1 -C 2 -alkyl or C 1 -C 2 -haloalkyl; C 6 -C 10 -aryl unsubstituted or substituted by C 1 -C 2 -alkyl, C 1 -C 2 -haloalkyl, C 1 -C 2 -alkoxy, C 1 -C 2 -haloalkoxy, halogen, cyano or C 1 -C 4 -alkoxycarbonyl; or 4- to 6-membered heterocyclyl unsubstituted or substituted by C 1 -C 2 -alkyl, C 1 -C 2 -haloalkyl, C 1 -C 2 -alkoxy, C 1 -C 2 -haloalkoxy, halogen, cyano or C 1 -C 4 -alkoxycarbonyl; and

R 7 and R 8 are each independently of the other H, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, unsubstituted or C 1 -C 4 -alkyl-substituted C 3 -C 6 -cycloalkyl, C 2 -C 6 -alkenyl or C 2 -C 6 -alkynyl.

2. A compound according to claim 1 , wherein B 1 , B 2 and B 3 are each CR 2 ′.

3. A compound according to claim 1 , wherein X is S(O) m , 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 m is an integer from 0 to 2.

4. A compound according to claim 1 , wherein R 1 is C 1 -C 3 -haloalkyl, in particular CF 3 .

5. A compound according to claim 1 , wherein R 1 is CF 3 .

6. A compound according to claim 1 of formula

wherein R 2 , X, X 1 , X 2 and Z are as defined in claim 1 and n is an integer of from 1 to 3.

7. A compound according to claim 6 , wherein Z is a group —C(O)-Q.

8. A compound according to claim 7 , wherein Q is straight-chain or branched C 1 -C 4 -alkyl, which is each unsubstituted or substituted by C 3 -C 6 -cycloalkyl, halogen, cyano, hydroxy, 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 -alkylsulfonyl, C 1 -C 2 -alkylcarbonylamino, C 1 -C 2 -haloalkylcarbonylamino or dioxolanyl; unsubstituted or methyl-substituted C 3 -C 6 -cycloalkyl; phenyl, which is unsubstituted or substituted by halogen, C 1 -C 2 -alkyl, C 1 -C 2 -haloalkyl, C 1 -C 2 -alkoxy, C 1 -C 2 -haloalkoxy, cyano or C 1 -C 4 -alkoxycarbonyl; thienyl, furyl, oxazolyl, thiazolyl, pyridyl or pyrimidinyl, which are each unsubstituted or substituted by C 1 -C 2 -alkyl, C 1 -C 2 -haloalkyl or C 1 -C 4 -alkoxycarbonyl; 1,3-dioxan-2-yl or 1,3-dioxolan-2-yl; or pyrrolidinyl, tetrahydrofuranyl, tetrahydrothiophenyl, piperidinyl, piperazinyl, morpholinyl, tetrahydropyranyl or thianyl which are each unsubstituted or substituted by C 1 -C 2 -alkyl, C 1 -C 2 -haloalkyl or C 1 -C 4 -alkoxycarbonyl.

9. A compound according to claim 7 , wherein Q is straight-chain or branched C 1 -C 4 -alkyl, cyclopropyl, cyclobutyl, halo-C 1 -C 3 -alkyl, cyano-C 1 -C 2 -alkyl, C 1 -C 2 -alkoxy-C 1 -C 2 -alkyl, C 1 -C 2 -alkylthio-C 1 -C 2 -alkyl, C 1 -C 2 -alkylsulfinyl-C 1 -C 2 -alkyl, C 1 -C 2 -alkylsulfonyl-C 1 -C 2 -alkyl, C 1 -C 2 -haloalkylcarbonylamino-C 1 -C 2 -alkyl, tetrahydrofuranyl or 2-(1,3-dioxolan-2yl)-n-propyl.

10. A compound of formula (Ia) according to claim 6 , wherein n is an integer from 1 to 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 , O or NR 5 ′; m is an integer from 0 to 2; R5′ 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 ′; R 3 ′ is H or C 1 -C 2 -alkyl; Z is a group —S(O) 2 -C 1 -C 2 -alkyl or a group —C(O)-Q; and Q is straight-chain or branched C 1 -C 4 -alkyl, which is each unsubstituted or substituted by C 3 -C 6 -cycloalkyl, halogen, cyano, C 1 -C 4 -alkoxy, C 1 -C 2 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 2 -haloalkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 2 -alkylcarbonylamino, C 1 -C 2 -haloalkylcarbonylamino or dioxolanyl; unsubstituted or methyl-substituted C 3 -C 6 -cycloalkyl; phenyl, which is unsubstituted or substituted by halogen, C 1 -C 2 -alkyl, C 1 -C 2 -haloalkyl, C 1 -C 2 -alkoxy, C 1 -C 2 -haloalkoxy, cyano or C 1 -C 4 -alkoxycarbonyl; thienyl, furyl, oxazolyl, thiazolyl, pyridyl or pyrimidinyl, which are each unsubstituted or substituted by C 1 -C 2 -alkyl, C 1 -C 2 -haloalkyl or C 1 -C 4 -alkoxycarbonyl; or pyrrolidinyl, tetrahydrofuranyl, tetrahydrothiophenyl, piperidinyl, piperazinyl, morpholinyl, tetrahydropyranyl or thianyl which is each unsubstituted or substituted by C 1 -C 2 -alkyl, C 1 -C 2 -haloalkyl or C 1 -C 4 -alkoxycarbonyl.

11. A compound of formula

including all geometric and stereoisomers, N-oxides, and salts thereof, wherein the radicals R 2 ′ are each independently of the other H, halogen or trifluoromethyl, subject to the proviso that at least 2 radicals R 2 ′ are not H; R 3 is hydrogen or methyl; Z is a radical —C(O)-Q; and Q is straight-chain or branched C 1 -C 4 -alkyl, cyclopropyl, cyclobutyl, C 1 -C 3 -haloalkyl, cyano-C 1 -C 2 -alkyl, C 1 -C 2 -alkoxy-C 1 -C 2 -alkyl, C 1 -C 2 -alkylthio-C 1 -C 2 -alkyl, C 1 -C 2 -alkylsulfinyl-C 1 -C 2 -alkyl, C 1 -C 2 -alkylsulfonyl-C 1 -C 2 -alkyl, C 1 -C 2 -haloalkyl-carbonylamino-C 1 -C 2 -alkyl, tetrahydrofuranyl or 2-(1,3-dioxolan-2yl)-n-propyl.

12. A compound of formula (Ib) according to claim 11 , which is

N-{5-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-thiophen-3-ylmethyl}-propionamide;

N-{5-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-thiophen-3-ylmethyl}-propionamide;

cyclopropanecarboxylic acid {2-methyl-5-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-di-hydro-isoxazol-3-yl]-thiophen-3-ylmethyl}-amide;

cyclopropanecarboxylic acid {2-methyl-5-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-di-hydro-isoxazol-3-yl]-thiophen-3-ylmethyl}-amide;

tetrahydro-furan-3-carboxylic acid {2-methyl-5-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-thiophen-3-ylmethyl}-amide; or

tetrahydro-furan-3-carboxylic acid {2-methyl-5-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-thiophen-3-ylmethyl}-amide.

13. A compound of formula

including all geometric and stereoisomers, N-oxides, and salts thereof, wherein the radicals R 2 ′ are each independently of the other H, halogen or trifluoromethyl, subject to the proviso that at least 2 radicals R 2 ′ are not H; R 3 is hydrogen or methyl; Z is a radical —C(O)-Q; and Q is straight-chain or branched C 1 -C 4 -alkyl, cyclopropyl, cyclobutyl, C 1 -C 3 -haloalkyl, cyano-C 1 -C 2 -alkyl, C 1 -C 2 -alkoxy-C 1 -C 2 -alkyl, C 1 -C 2 -alkylthio-C 1 -C 2 -alkyl, C 1 -C 2 -alkylsulfinyl-C 1 -C 2 -alkyl, C 1 -C 2 -alkylsulfonyl-C 1 -C 2 -alkyl, C 1 -C 2 -haloalkyl-carbonylamino-C 1 -C 2 -alkyl, tetrahydrofuranyl or 2-(1,3-dioxolan-2yl)-n-propyl.

14. A compound of formula (Ic) according to claim 13 , which is

N-{5-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-furan-3-ylmethyl}-propionamide;

N-{5-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-furan-3-ylmethyl}-propionamide;

cyclopropanecarboxylic acid {2-methyl-5-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-di-hydro-isoxazol-3-yl]-furan-3-ylmethyl}-amide;

cyclopropanecarboxylic acid {2-methyl-5-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-di-hydro-isoxazol-3-yl]-furan-3-ylmethyl}-amide;

tetrahydro-furan-3-carboxylic acid {2-methyl-5-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-furan-3-ylmethyl}-amide; or

tetrahydro-furan-3-carboxylic acid {2-methyl-5-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-furan-3-ylmethyl}-amide.

15. A 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.

16. A composition for the control of parasites, comprising as active ingredient at least one compound of formula (Ib) according to claim 11 , in addition to a carrier and/or a dispersant.

17. A composition for the control of parasites, comprising as active ingredient at least one compound of formula (Ic) according to claim 13 , in addition to a carrier and/or a dispersant.

18. A method of controlling parasites in and on vertebrates, which comprises applying to the vertebrates a pharmaceutically effective amount of at least one compound of formula (I) according to claim 1 .

19. A method of controlling parasites in and on vertebrates, which comprises applying to the vertebrates a pharmaceutically effective amount of at least one compound of formula (Ia) according to claim 6 .

20. A method of controlling parasites in and on vertebrates, which comprises applying to the vertebrates a pharmaceutically effective amount of at least one compound of formula (Ib) according to claim 11 .

21. A method of controlling parasites in and on vertebrates, which comprises applying to the vertebrates a pharmaceutically effective amount of at least one compound of formula (Ic) according to claim 13 .