5-aryl isoxazolines for controlling pests

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,

n is an integer from 0 to 4; 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;

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;

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;

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; 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 ; CO 2 R 7 ;

COR 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, NHCOR 7 , C 1 -C 6 -alkoxycarbonyl, sulfonamido, N-mono- or N,N, di-C 1 -C 4 -alkylsulfonamido, CONR 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 -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 5 are each independently of the other H, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl or C 3 -C 6 -cycloalkyl, alkylcycloalkyl, C 2 -C 6 -alkenyl or C 2 -C 6 -alkynyl.

2. A compound of formula (I) according to claim 1 , wherein 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 ; CO 2 R 7 ; COR 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, C 1 -C 6 -alkylcarbonylamino, C 1 -C 6 -haloalkylcarbonylamino, C 1 -C 6 -alkoxycarbonyl, sulfonamido, N-mono- or N,N, di-C 1 -C 4 -alkylsulfonamido, N-mono- or N,N-di-C 1 -C 6 -alkylaminocarbonyl, N-mono- or N,N-di-C 1 -C 6 -haloalkylaminocarbonyl, 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;

R 7 and R 3 are each independently of the other H, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl or C 3 -C 6 -cycloalkyl;

and B 1 , B 2 , B 3 , R 1 , R 2 , R 2 ′, R 3 , R 3 ′, R 4 , R 5 , R 5 ′, R 6 , X, X 1 , X 2 , Z, m, n and t are each as defined in claim 1 .

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

4. 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.

5. A compound according to claim 1 , wherein X is O, 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.

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

7. A compound according to claim 1 of formula

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

8. The compound of claim 7 , wherein Z is a group —C(O)-Q.

9. The compound of claim 8 , 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 or C 1 -C 2 -haloalkylcarbonylamino; 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 are each unsubstituted or substituted by C 1 -C 2 -alkyl, C 1 -C 2 -haloalkyl or C 1 -C 4 -alkoxycarbonyl.

10. The compound of claim 8 , wherein Q is straight-chain or branched C 1 -C 4 -alkyl, C 1 -C 3 -haloalkyl, cyclopropylmethyl, 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 or C 1 -C 2 -alkylsulfonyl-C 1 -C 2 -alkyl.

11. A compound of formula (Ia) according to claim 7 , 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; 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 ′; 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 or C 1 -C 2 -haloalkylcarbonylamino; 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.

12. A compound according to claim 1 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; 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, C 1 -C 3 -haloalkyl, cyclopropylmethyl, 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 or C 1 -C 2 -alkylsulfonyl-C 1 -C 2 -alkyl.

13. A compound according to claim 1 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; 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, C 1 -C 3 -haloalkyl, cyclopropylmethyl, 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 or C 1 -C 2 -alkylsulfonyl-C 1 -C 2 -alkyl.

14. A composition for the control of parasites, comprising as active ingredient at least one compound of the formula (1) according to claim 1 , in addition to a carrier and/or a dispersant.

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