Isoxazoline derivatives as pesticides
View Patent ↗Novel isoxazoline compounds and compositions containing the compounds are disclosed. The compounds have pesticidal properties and are suitable for use on non-human animals.
1. 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 -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, 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. A compound of formula (I) according to 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. 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 , 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. A compound according to claim 1 , wherein R 1 is halo-C 1 -C 3 -alkyl.
6. A compound according to claim 5 , wherein R 1 is CF 3 .
7. A compound according to claim 1 of formula
wherein R 1 , R 2 , X, X 1 , X 2 , Z and n are as defined in claim 1 .
8. A compound of formula (Ia) according to 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, wherein R and r are as defined.
9. A compound of formula (Ia) according to 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. A compound according to claim 9 , wherein m is 0.
11. A compound of formula (Ia) according to 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. A compound according to claim 11 , wherein (alk) is methylene.
13. A compound of formula (Ia) according to 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. A compound according to claim 13 , wherein (alk) is methylene.
15. A compound according to 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. A compound according to 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. A compound according to claim 16 , wherein Z is the radical Q-34, wherein r is 0.
18. A compound according to claim 15 , wherein Z is a 5- or 6-membered heterocyclic ring having from 1 to 3 same or different heteroatoms.
19. A compound according to 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, 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.
20. A compound according to claim 19 , 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.
21. A compound of formula (I) according to 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. A compound of formula (I) according to 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. A compound of formula (I) according to claim 1 , which 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-dihydro-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. 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.
25. 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 .