Isoxazolines derivatives and their use as pesticide
View Patent ↗Novel isoxazoline compounds, compositions containing the compounds and methods for making the compounds are disclosed. The compounds and compositions have pesticidal properties and are suitable for controlling ectoparasites on non-human animals.
1. A compound of formula
including geometric and stereoisomers, N-oxides, and salts thereof, wherein
A 1 , A 2 , A 3 , A 4 , A 5 and A 6 are each independently selected from the group consisting of CR 3 ′ and N;
n is an integer from 0 to 4;
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 ;
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 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, —CN or —NO 2 ;
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 -alkylsulfonyl, —CN or —NO 2 ;
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 3 -C 6 -cycloalkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, 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, —CN, —NO 2 , amino, N-mono- or N,N-di-C 1 -C 6 -alkylamino, CO 2 H, C 1 -C 6 -alkoxycarbonyl, sulfonamido, N-mono- or N,N,di-C 1 -C 6 -alkylsulfonamido, CONH 2 , N-mono- or N,N,di-C 1 -C 6 -alkylaminocarbonyl, N-mono- or N,N,di-C 1 -C 6 -haloalkylaminocarbonyl, N—C 1 -C 2 -haloalkylaminocarbonyl-C 1 -C 2 -alkylaminocarbonyl, C 1 -C 6 -alkylcarbonylamino, C 2 -C 6 -alkanoyl, C 2 -C 6 -haloalkanoyl, CH 2 R 5 , a group C(O)N═CHN(CH 3 ) 2 , a group C(O)N═CHNHOCH 3 , pyrrolidonylcarbonyl, and unsubstituted or halogen-, C 1 -C 6 -alkyl-, C 1 -C 6 -haloalkyl-, C 1 -C 6 -alkoxy-, C 1 -C 6 -haloalkoxy-, nitro- or cyano-substituted phenyl, benzyl, phenethyl, pyridyl, pyridinylmethyl, pyrimidinyl, pyrimidinylmethyl, benzoyl or phenoxy; and
R 5 is CO 2 H, C 1 -C 6 -alkoxycarbonyl, CONH 2 , N-mono- or N,N,di-C 1 -C 6 -alkylaminocarbonyl, N-mono- or N,N,di-C 1 -C 6 -haloalkylaminocarbonyl, C 1 -C 6 -alkylcarbonylamino, pyridinylaminocarbonyl or tetrahydrofuranyl.
2. A compound of formula (I) according to claim 1 , wherein
A 1 , A 2 , A 3 , A 4 , A 5 and A 6 are each independently selected from the group consisting of CR 3 ′ and N;
n is an integer from 0 to 4;
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 ;
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 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, —CN or —NO 2 ;
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 -alkylsulfonyl, —CN or —NO 2 ; and
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, —CN, —NO 2 , amino, N-mono- or N,N-di-C 1 -C 6 -alkylamino, C 2 -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 -alkylcarbonylamino, 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-, nitro- or cyano-substituted phenyl, benzyl, benzoyl or phenoxy.
3. A compound according to claim 1 of formula (I), wherein B 1 , B 2 and B 3 are each CR 2 ′.
4. A compound according to claim 1 , wherein A 1 , A 2 , A 3 , A 4 , A 5 and A 6 are each CH.
5. A compound according to claim 1 , wherein R 1 is C 1 -C 3 -haloalkyl.
6. A compound according to claim 1 of formula
wherein R 1 , R 2 , R 3 , Q and n are as defined in claim 1 , and m is an integer from 0 to 4.
7. A compound according to claim 1 , wherein Q 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, —CN, —NO 2 , 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.
8. A compound according to claim 1 , wherein Q is a radical of formula
wherein r is an integer from 0 to 3 and R is independently 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, —CN, —NO 2 , and C 1 -C 4 -alkoxycarbonyl.
9. A compound according to claim 8 , wherein Q is the radical Q-34, Q-43 or Q-47, wherein r is in each case 0.
10. A compound of formula (Ia) according to claim 6 , wherein
n is an integer from 1 to 3, R 1 is C 1 -C 3 -haloalkyl, each R 2 and R 3 is independently 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, —CN and —NO 2 , m is an integer from 0 to 2, and Q is either (i) phenyl, which is unsubstituted or substituted by 1 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, —CN, —NO 2 , and unsubstituted or halogen-, C 1 -C 2 -alkyl-, C 1 -C 2 -haloalkyl-, C 1 -C 2 -alkoxy-, C 1 -C 2 -haloalkoxy-, —CN and —NO 2 -substituted phenyl or phenoxy, or is
(ii) a 5- or 6-membered heterocyclic ring having from 1 to 3 same or different heteroatoms selected from the group consisting of N, O and S, which is further 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, C 1 -C 2 -haloalkylthio, —CN, —NO 2 or C 1 -C 4 -alkoxycarbonyl, or is
(iii) a fused hetero-bicyclic ring system comprising a 5- or 6-membered heterocyclic ring having from 1 to 3 same or different heteroatoms selected from the group consisting of N, O and S, to which is attached an annulated ring, and which is further 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, C 1 -C 2 -haloalkylthio, —CN, —NO 2 or C 1 -C 4 -alkoxycarbonyl.
11. A compound of formula (Ia) according to claim 6 , 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 2 -haloalkyl, C 1 -C 2 -haloalkoxy and —CN, m is 0 and Q is either
(ii) a 5- or 6-membered heteroaromatic ring selected from the group consisting of the radicals given in claim 7 , or is
(iii) a fused hetero-bicyclic ring system selected from the group consisting of the radicals
12. A compound of formula (Ia) according to claim 6 , 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 2 -haloalkyl, C 1 -C 2 -haloalkoxy and —CN, m is 0 and Q is a radical
wherein r is an integer of 0 or 1, and R is independently selected from the group consisting of C 1 -C 2 -alkyl, halo-C 1 -C 2 -alkyl, halo-C 1 -C 2 -alkylcarbonyl, cyano, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkoxycarbonylmethyl, carboxy-C 1 -C 2 -alkyl, aminocarbonyl, N-mono- or N,N-di-C 1 -C 2 -alkylaminocarbonyl, halo-C 1 -C 2 -alkylaminocarbonylmethyl, halo-C 1 -C 2 -alkylaminocarbonylmethylaminocarbonyl, halovinyl, —C(O)N═CHN(CH 3 ) 2 , —C(O)N═CHNHOCH 3 , unsubstituted or halogen- or C 1 -C 2 -alkoxy-substituted phenyl, benzyl and phenylethyl, unsubstituted and halogen-substituted 2-, 3- and 4-pyridyl and pyridylmethyl, pyridylcarbonylaminomethyl, pyrrolidinecarbonyl, and 2-tetrahydrofuranylmethyl.
13. A compound according to claim 5 , wherein R 1 is CF 3 .
14. A compound according to claim 7 , wherein Q is a 5- or 6-membered heterocyclic ring having from 1 to 3 same or different heteroatoms.
15. A compound according to claim 10 , wherein m is 0.
16. A compound according to claim 10 , wherein Q is phenyl, which is substituted by 1 or 2 same or different substituents.
17. A compound according to claim 12 , wherein Q is the radical Q-24, Q-26, Q-30, Q-32, Q-34, Q-44 or Q-47.
18. 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.
19. 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 .