Compounds for the control of endoparasites
View Patent ↗The invention relates to compounds of the general formula (I) wherein the variable have the meanings as indicated in the claims, or a physiologically acceptable salt thereof. The active ingredients have advantageous pesticidal properties. They are especially suitable for controlling endoparasites in warm-blooded animals.
1. A compound of formula
wherein Z 1 and Z 2 are each independently N or CR 1′ ;
R 1 and R 1′ are each independently of the other H, halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 3 -haloalkoxyl, C 1 -C 4 -alkylthio, halo-C 1 -C 4 -alkylthio, SF 5 , amino, N-mono- or N,N-di-C 1 -C 4 -alkylamino, aminosulfonyl, N-mono- or N,N-di-C 1 -C 4 -alkylaminosulfonyl, N-mono- or N,N-di-halo-C 1 -C 4 -alkylaminosulfonyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -alkylsulfonylamino, halo-C 1 -C 4 -alkylsulfonyl, halo-C 1 -C 4 -alkylsulfinyl, halo-C 1 -C 4 -alkylsulfonylamino or benzylsulfonylamino;
Q is Ar 1 or —C(O)—(O) m —R 2 ;
m is 0 or 1; R 2 is C 1 -C 6 -alkyl or C 3 -C 8 -cycloalkyl;
Ar 1 is (i) phenyl which is substituted by 1 to 2 same or different substituents selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxyl, C 1 -C 4 -alkylthio, halo-C 1 -C 4 -alkylthio, SF 5 , amino, N-mono- or N,N-di-C 1 -C 4 -alkylamino, aminosulfonyl, N-mono- or N,N-di-C 1 -C 4 -alkylaminosulfonyl, N-mono- or N,N-di-halo-C 1 -C 4 -alkylaminosulfonyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -alkylsulfonylamino, benzylsulfonylamino, halo-C 1 -C 4 -alkylsulfonyl, halo-C 1 -C 4 -alkylsulfinyl and halodioxolyl; or is (ii) heteroaryl selected from the group consisting of 2-, 3- or 4-pyridyl and 2- or 3-thiophenyl which is each unsubstituted or substituted by methyl, ethyl, halogen, CF 3 or carboxy;
Ar 2 is phenyl which is substituted by 1 to 3 same or different substituents selected from the group consisting of halogen, cyano, nitro, 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, halo-C 1 -C 4 -alkylthio, SF 5 , amino, N-mono- or N,N-di-C 1 -C 4 -alkylamino, aminosulfonyl, N-mono- or N,N-di-C 1 -C 4 -alkylaminosulfonyl, N-mono- or N,N-di-halo-C 1 -C 4 -alkylaminosulfonyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -alkylsulfonylamino, benzylsulfonylamino, halo-C 1 -C 4 -alkylsulfonyl, halo-C 1 -C 4 -alkylsulfinyl and halodioxolyl;
L 1 is a bifunctional linker radical of formula
L 2 is a bifunctional linker radical of formula
A and B are each independently C 3 -C 8 -hetero-cycloalkylene or C 5 -C 10 -hetero-bicycloalkylene comprising two N-atoms, respectively which is each unsubstituted or substituted by C 1 -C 2 -alkyl;
A 1 , A 2 , and B 2 are each independently C 3 -C 8 -hetero-cycloalkylene comprising a N-atom, respectively;
R and R′ are each independently of the other H or C 1 -C 4 -alkyl;
or a physiologically acceptable salt thereof.
2. The compound according to claim 1 , wherein R 1 and R 1′ are each independently of the other H, cyano, methyl or methoxy.
3. The compound according to claim 1 , wherein Z 1 is N and Z 2 is CR 1′ .
4. The compound of formula (I) according to claim 3 , wherein Q is Ar 1 and Ar 1 is phenyl which is substituted by 1 or 2 same or different radicals selected from the group consisting of halogen, cyano and C 1 -C 2 -haloalkyl.
5. The compound of formula (I) according to claim 3 , wherein Q is a radical —C(O)—(O) m —R 2 , wherein R 2 is C 1 -C 4 -alkyl or C 3 -C 6 -cycloalkyl.
6. The compound of formula (I) according to claim 5 , wherein Ar 2 is phenyl which is substituted by 1 or 2 same or different radicals selected from the group consisting of halogen, cyano, nitro, C 1 -C 2 -haloalkyl, C 1 -C 2 -haloalkoxy or C 1 -C 2 -haloalkylthio.
7. The compound of formula (I) according to claim 6 , wherein the linker L 1 is of formula
wherein s and r are each independently an integer 1 or 2, r′ is an integer 0, 1 or 2, s′ is an integer 0, 1 or 2 and R is H or methyl.
8. The compound of formula (I) according to claim 7 , wherein the linker L 2 is a radical of formula
wherein r″ is 0 or 1, s′ is an integer 1 or 2 and R′ is H or methyl.
9. The compound of formula (I) according to claim 6 , wherein L 1 is a radical
and L 2 is a radical
10. The compound according to claim 1 of formula
wherein R 1 , R 2 , m, L 1 , L 2 , Z 1 , Z 2 and Ar 2 are each as defined in claim 1 .
11. The compound according to claim 1 of formula
wherein R 1 , Ar 1 , Ar 2 , L 1 , L 2 , Z 1 and Z 2 are each as defined in claim 1 .
12. The compound according to claim 1 of formula
wherein Q is 4-CF 3 -phenyl, 5-CF 3 -pyrid-2-yl, 6-CF 3 -pyrid-3-yl, —C(O)—O—tert-butyl or —C(O)-cyclopropyl;
Z 1 is N or CH;
Z 2 is N or CH;
L 1 is a radical,
L 2 is a radical
R 3 is CF 3 ; and R 3′ is cyano or nitro, or a physiologically acceptable salt thereof.
13. A method of controlling endoparasites, in warm-blooded animals, which comprises administering to the warm-blooded animals a veterinary effective amount of at least one compound of formula
wherein Z 1 and Z 2 are each independently N or CR 1′ ;
R 1 and R 1′ are each independently of the other H, halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 3 -haloalkoxyl, C 1 -C 4 -alkylthio, halo-C 1 -C 4 -alkylthio, SF 5 , amino, N-mono- or N,N-di-C 1 -C 4 -alkylamino, aminosulfonyl, N-mono- or N,N-di-C 1 -C 4 -alkylaminosulfonyl, N-mono- or N,N-di-halo-C 1 -C 4 -alkylaminosulfonyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -alkylsulfonylamino, halo-C 1 -C 4 -alkylsulfonyl, halo-C 1 -C 4 -alkylsulfinyl, halo-C 1 -C 4 -alkylsulfonylamino or benzylsulfonylamino;
Q is Ar 1 or —C(O)—(O) m —R 2 ;
m is 0 or 1; R 2 is C 1 -C 6 -alkyl or C 3 -C 8 -cycloalkyl;
Ar 1 is (i) phenyl which is substituted by 1 to 2 same or different substituents selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxyl, C 1 -C 4 -alkylthio, halo-C 1 -C 4 -alkylthio, SF 5 , amino, N-mono- or N,N-di-C 1 -C 4 -alkylamino, aminosulfonyl, N-mono- or N,N-di-C 1 -C 4 -alkylaminosulfonyl, N-mono- or N,N-di-halo-C 1 -C 4 -alkylaminosulfonyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -alkylsulfonylamino, benzylsulfonylamino, halo-C 1 -C 4 -alkylsulfonyl, halo-C 1 -C 4 -alkylsulfinyl and halodioxolyl; or is (ii) heteroaryl selected from the group consisting of 2-, 3- or 4-pyridyl and 2- or 3-thiophenyl which is each unsubstituted or substituted by methyl, ethyl, halogen, CF 3 or carboxy;
Ar 2 is phenyl which is substituted by 1 to 3 same or different substituents selected from the group consisting of halogen, cyano, nitro, 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, halo-C 1 -C 4 -alkylthio, SF 5 , amino, N-mono- or N,N-di-C 1 -C 4 -alkylamino, aminosulfonyl, N-mono- or N,N-di-C 1 -C 4 -alkylaminosulfonyl, N-mono- or N,N-di-halo-C 1 -C 4 -alkylaminosulfonyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -alkylsulfonylamino, benzylsulfonylamino, halo-C 1 -C 4 -alkylsulfonyl, halo-C 1 -C 4 -alkylsulfinyl and halodioxolyl;
L 1 is a bifunctional linker radical of formula
L 2 is a bifunctional linker radical of formula
A and B are each independently C 3 -C 8 -hetero-cycloalkylene or C 5 -C 10 -hetero-bicycloalkylene comprising two N-atoms, respectively which is each unsubstituted or substituted by C 1 -C 2 -alkyl;
A 1 , A 2 , and B 2 are each independently C 3 -C 8 -hetero-cycloalkylene comprising a N-atom, respectively;
R and R′ are each independently of the other H or C 1 -C 4 -alkyl;
or a physiologically acceptable salt thereof.
14. The method according to claim 13 , wherein R 1 and R 1′ are each independently of the other H, cyano, methyl or methoxy.
15. The method according to claim 13 , wherein Z 1 is N and Z 2 is CR 1′ .
16. The method according to claim 15 , wherein Q is Ar 1 and Ar 1 is phenyl which is substituted by 1 or 2 same or different radicals selected from the group consisting of halogen, cyano and C 1 -C 2 -haloalkyl.
17. The method according to claim 15 , wherein Q is a radical —C(O)—(O) m —R 2 , wherein R 2 is C 1 -C 4 -alkyl or C 3 -C 6 -cycloalkyl.
18. The method according to claim 17 , wherein Ar 2 is phenyl which is substituted by 1 or 2 same or different radicals selected from the group consisting of halogen, cyano, nitro, C 1 -C 2 -haloalkyl, C 1 -C 2 -haloalkoxy or C 1 -C 2 -haloalkylthio.
19. The method according to claim 18 , wherein the linker L 1 is of formula
wherein s and r are each independently an integer 1 or 2, r′ is an integer 0, 1 or 2, s′ is an integer 0, 1 or 2 and R is H or methyl.
20. The method according to claim 19 , wherein the linker L 2 is a radical of formula
wherein r″ is 0 or 1, s′ is an integer 1 or 2 and R′ is H or methyl.
21. The method according to claim 20 , wherein L 1 is a radical
and L 2 is a radical
22. The method according to claim 21 , wherein the at least one compound of formula (I) is a compound of formula
23. The method according to claim 13 , wherein the at least one compound of formula (I) is a compound of formula
wherein R 1 , Ar 1 , Ar 2 , L 1 , L 2 , Z 1 and Z 2 are each as defined in claim 13 .
24. The method according to claim 13 , wherein the at least one compound of formula (I) is a compound of formula
wherein Q is 4-CF 3 -phenyl, 5-CF 3 -pyrid-2-yl, 6-CF 3 -pyrid-3-yl, —C(O)—O—tert-butyl or —C(O)-cyclopropyl;
Z 1 is N or CH;
Z 2 is N or CH;
L 1 is a radical,
L 2 is a radical
R 3 is CF 3 ; and R 3′ is cyano or nitro, or a physiologically acceptable salt thereof.