Isoxazoline-substituted benzamide compound and pesticide
A substituted alkenylbenzene compound of formula (4): wherein X 1 is a halogen atom, —SF 5 , C 1 -C 6 haloalkyl, hydroxy C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy C 1 -C 6 haloalkyl, C 3 -C 8 halocycloalkyl, C 1 -C 6 haloalkoxy, C 1 -C 3 haloalkoxy C 1 -C 3 haloalkoxy, C 1 -C 6 haloalkylthio, C 1 -C 6 haloalkylsulfinyl or C 1 -C 6 haloalkylsulfonyl; X 3 is a hydrogen, halogen, cyano, nitro, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy or C 1 -C 6 alkylthio; X 4 is a hydrogen, halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy; R 3 is —C(R 3a )(R 3b )R 3c , where R 3a and R 3b are a halogen, or R 3a and R 3b together form a 3 - to 6 -membered ring together with the carbon bonding them by forming a C 2 -C 5 haloalkylene chain, and R 3c is a hydrogen, halogen, C 1 -C 5 alkyl, C 1 -C 5 haloalkyl, C 1 -C 4 haloalkoxy or C 1 -C 4 haloalkylthio, with a proviso that where X 1 is a fluorine, chlorine or trifluoromethyl, and X 2 and X 3 are hydrogen, where X 1 and X 2 are fluorine and X 3 is a hydrogen, or where X 1 and X 2 are trifluoromethyl and X 3 is a hydrogen, R 3c is a hydrogen, chlorine, bromine, iodine, C 1 -C 5 alkyl, C 1 -C 5 haloalkyl, C 1 -C 4 haloalkoxy or C 1 -C 4 haloalkylthio.
1. A method for protecting animals against a parasitic pest comprising administration of a pesticidally effective amount of one or more isoxazoline-substituted benzamide compounds, an optically active form or the salt thereof according to a formula 1
wherein A 1 , A 2 and A 3 are carbon atom,
G is benzene ring,
W is oxygen atom,
X is halogen atom, cyano, C 1 -C 6 alkyl, C 1 -C 6 alkyl arbitrarily substituted with R 4 or —OR 5 ,
Y is halogen atom, C 1 -C 6 alkyl, C 1 -C 6 alkyl arbitrarily substituted with R 4 or —OR 5 ,
R 1 and R 2 independently of each other are hydrogen atom, C 1 -C 12 alkyl, C 1 -C 12 alkyl arbitrarily substituted with R 16 , C 3 -C 12 cycloalkyl, C 3 -C 12 cycloalkyl arbitrarily substituted with R 16 , —C(O)R 9 , —C(O)OR 9 , E-3 to E-7, E-23 to E-27 or E-28,
R 3 is C 1 -C 6 alkyl arbitrarily substituted with R 4 ,
D-21 to D-23 and D-47 to D-49 are aromatic heterocyclic rings of the following formulae, respectively
Z is halogen atom, cyano, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl or C 1 -C 6 haloalkoxy,
E-2 to E-7, E-23 to E-28 are saturated heterocyclic rings of the following formulae, respectively
R 4 is halogen atom,
R 5 is C 1 -C 6 alkyl arbitrarily substituted with R 24 ,
R 9 is C 1 -C 6 alkyl or C 1 -C 6 alkyl arbitrarily with R 24 ,
R 16 is halogen atom, —OR 25 , —S(O) r R 27 , —C(O)N(R 29 )R 28 , D-21 to D-23, D-47 to D-49, E-2 to E-7, E-23 to E-27 or E-28,
R 22 is halogen atom, cyano, C 1 -C 6 alkyl, C 1 -C 6 alkoxy or C 1 -C 6 alkylthio,
R 24 is halogen atom,
R 25 is hydrogen atom, C 1 -C 8 alkyl, C 1 -C 8 alkyl arbitrarily substituted with R 32 , —CHO, —C(O)R 33 , —C(O)OR 33 , D-21 to D-23, D-47, D-48 or D-49,
R 27 is C 1 -C 8 alkyl, C 1 -C 8 alkyl arbitrarily substituted with R 32 , D-21 or D-47,
R 28 is C 1 -C 6 alkyl, C 1 -C 6 alkyl arbitrarily substituted with R 32 , C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkyl arbitrarily substituted with R 32 , C 2 -C 8 alkenyl, C 2 -C 8 alkenyl arbitrarily substituted with R 32 or C 2 -C 8 alkynyl,
R 29 is hydrogen atom, C 1 -C 6 alkyl or C 1 -C 6 alkyl arbitrarily substituted with R 32 ,
R 32 is halogen atom, cyano, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, —OH, —OR 33 , —S(O) r R 33 , D-21 to D-23, D-47 D-48 or D-49,
R 33 is C 1 -C 6 alkyl or C 1 -C 6 haloalkyl,
m is an integer of 1 to 3
n is an integer of 1,
p2 is an integer of 0 to 2,
p4 is an integer of 0 to 2,
q2 is an integer of 0 to 3,
q3 is an integer of 0 to 3,
q4 is an integer of 0 to 3,
r is an integer of 0 to 2, and
t is an integer of 0.
2. The method of claim 1 wherein
Y is C 1 or CH 3 ;
R 1 is H;
R 2 is C 1 -C 6 alkyl substituted with one R 16 ; and
R 16 is OR 25 , S(O)nR 27 or C(O)NR 29 R 28 .
3. The method of claim 2 wherein
X is hydrogen, halogen, C 1 -C 6 alkyl arbitrarily substituted with R 4 , or OR 5 ;
and each X may be identical with or different from each other.
4. The method of claim 3 wherein
Y is CH 3 ; and
R 16 is C(O)NR 29 R 28 .
5. The method of claim 4 wherein
X m is 3-CF 3 -5-CF 3 .
6. The method of claim 4 wherein
R 29 is H; and
R 28 is C 1 -C 6 alkyl or C 1 -C 6 alkyl substituted with halogen.
7. The method of claim 4 wherein
R 29 is H; and
R 28 is cyclopropyl.
8. The method of claim 1 wherein the pesticidally effective amount of a compound of Formula 1 is administered orally.
9. The method of claim 1 wherein the pesticidally effective amount of a compound of Formula 1 is administered parenterally.
10. The method of claim 9 wherein the pesticidally effective amount of a compound of Formula 1 is administered by injection.
11. The method of claim 1 wherein the animal to be protected is a mammal.
12. The method of claim 11 wherein the mammal to be protected is livestock.
13. The method of claim 11 wherein the mammal to be protected is a canine.
14. The method of claim 11 wherein the mammal to be protected is a feline.
15. The method of claim 1 wherein the parasitic pest is an ectoparasite.
16. The method of claim 1 wherein the parasitic pest is an arthropod.
17. The method of claim 1 wherein the parasitic pest is a fly, mosquito, mite, tick, louse, flea, true bug or maggot.
18. The method of claim 17 wherein the animals to be protected are a cat or dog and the parasitic pest is a flea, tick or mite.
19. The method according to claim 1 , wherein the isoxazoline-substituted benzamide compounds, an optically active form or the salt thereof are according to a formula
wherein,
(X) m is 3,5-Cl 2 , 3-Br, 3-I, 4-I, 3-CF 3 , 3-OCF 3 , 3,5-F 2 , 3,5-Br 2 , 3,5-(CF 3 ) 2 , 3,4-Cl 2 or 3,5-Cl 2 -4-CH 3 ,
Y is H, CH 3 , Br, CH 2 CH 3 , Cl, I or OCF 3 ,
R 1 is CH(CH 3 )CH 2 OCH 3 , 2-tetrahydrofuryl, CH 2 CF 3 , CH 2 (2-pyridyl), cyclobutyl, CH 2 CH 2 OCH 2 CH 3 , tetrahydrofurfuryl, CH 2 CH 2 SCH 2 CH 3 , CH 2 CH(CH 3 )S(O)CH 3 , CH 2 CH(CH 3 )SO 2 CH 3 , CH 2 C(O)NHCH 3 , CH 2 C(O)N(CH 3 ) 2 , CH 2 C(O)NHCH 2 CH 3 , CH 2 C(O)NHPr-i, CH 2 C(O)NHCH 2 CH 2 Cl, CH 2 C(O)NHCH 2 CF 3 , CH 2 C(O)NHCH 2 CH═CH 2 , CH 2 C(O)N(CH 3 )CH 2 CH═CH 2 , CH 2 C(O)NHCH 2 C≡CH, CH(CH 3 )C(O)NHCH 2 CH 2 Cl, CH 2 (4-trifluoromethylthiazol-2-yl), CH 2 (4-thiazolyl), CH 2 (2-chlorothiazol-5-yl), CH 2 (2-pyridyl), CH(CH 3 )(2-pyridyl), CH 2 (4-chloropyridin-2-yl), CH 2 (6-chloropyridin-2-yl), CH 2 (3-pyridyl), CH 2 (2-chloropyridin-5-yl), CH 2 CH 2 OCH 3 , CH 2 CH 2 CF 3 , CH(CF 3 )OCH 3 , CH(CH 3 )C(O)NHCH 2 CF 3 , CH(CH 3 )(2-thiazolyl), CH 2 OCH 3 , CH 2 OCH 2 CH 3 , CH 2 OCH 2 CH 2 CH 3 , CH 2 OCH(CH 3 ) 2 , CH 2 OCH 2 CH 2 Cl, CH 2 OCH 2 CHF 2 , CH 2 OCH 2 CF 3 , CH(CH 3 )OH, 3-tetrahydrofuryl(R), 2-tetrahydropyranyl, CH 2 SCH 3 , CH 2 S(O)CH 3 , CH 2 SO 2 CH 3 , CH 2 (2-methylthiothiazol-4-yl), 6-methoxy-2-tetrahydropyranyl or CH 2 (4-pyridyl),
R 2 is H, CH 3 , CH 2 CF 3 , C(O)CH 3 , C(O)CH 2 CH 3 , C(O)OCH 3 , C(O)OBu-i, C(O)OCH 2 CH 2 Cl, CH 2 CH 3 , cyclopropyl, CH 2 OCH 2 CH 3 or CH 2 OCH 3 , and
R 3 is CF 3 , CHF 2 , CF 2 Cl or CF 2 CF 3 .
20. A method for protecting a mammal against fleas comprising oral administration to the mammal of a pesiticidally effective amount of one or more isoxazoline-substituted benzamide compounds, an optically active form or the salt thereof according to a formula 1
wherein A 1 , A 1 and A 3 are carbon atom,
G is benzene ring,
W is oxygen atom,
X is halogen atom, cyano, C 1 -C 6 alkyl, C 1 -C 6 alkyl arbitrarily substituted with R 4 or —OR 5 ,
Y is halogen atom, C 1 -C 6 alkyl, C 1 -C 6 alkyl arbitrarily substituted with R 4 or —OR 5 ,
R 1 and R 2 independently of each other are hydrogen atom, C 1 -C 12 alkyl, C 1 -C 12 alkyl arbitrarily substituted with R 16 , C 3 -C 12 cycloalkyl, C 3 -C 12 cycloalkyl arbitrarily substituted with R 16 , —C(O)R 9 , —C(O)OR 9 , E-3 to E-7, E-23 to E-27 or E-28,
R 3 is C 1 -C 6 alkyl arbitrarily substituted with R 4 ,
D-21 to D-23 and D-47 to D-49 are aromatic heterocyclic rings of the following formulae, respectively
Z is halogen atom, cyano, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl or C 1 -C 6 haloalkoxy,
E-2 to E-7, E-23 to E-28 are saturated heterocyclic rings of the following formulae, respectively
R 4 is halogen atom,
R 5 is C 1 -C 6 alkyl arbitrarily substituted with R 24 ,
R 9 is C 1 -C 6 alkyl or C 1 -C 6 alkyl arbitrarily with R 24 ,
R 16 is halogen atom, —OR 25 , —S(O) r R 27 , —C(O)N(R 29 )R 28 , D-21 to D-23, D-47 to D-49, E-2 to E-7, E-23 to E-27 or E-28,
R 22 is halogen atom, cyano, C 1 -C 6 alkyl, C 1 -C 6 alkoxy or C 1 -C 6 alkylthio,
R 24 is halogen atom,
R 25 is hydrogen atom, C 1 -C 8 alkyl, C 1 -C 8 alkyl arbitrarily substituted with R 32 , —CHO, —C(O)R 33 , —C(O)OR 33 , D-21 to D-23, D-47, D-48 or D-49,
R 27 is C 1 -C 8 alkyl, C 1 -C 8 alkyl arbitrarily substituted with R 32 , D-21 or D-47,
R 28 is C 1 -C 6 alkyl, C 1 -C 6 alkyl arbitrarily substituted with R 32 , C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkyl arbitrarily substituted with R 32 , C 2 -C 8 alkenyl, C 2 -C 8 alkenyl arbitrarily substituted with R 32 or C 2 -C 8 alkynyl,
R 29 is hydrogen atom, C 1 -C 6 alkyl or C 1 -C 6 alkyl arbitrarily substituted with R 32 ,
R 32 is halogen atom, cyano, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, —OH, —OR 33 , —S(O) r R 33 , D-21 to D-23, D-47 D-48 or D-49,
R 33 is C 1 -C 6 alkyl or C 1 -C 6 haloalkyl,
m is an integer of 1 to 3
n is an integer of 1,
p2 is an integer of 0 to 2,
p4 is an integer of 0 to 2,
q2 is an integer of 0 to 3,
q3 is an integer of 0 to 3,
q4 is an integer of 0 to 3,
r is an integer of 0 to 2, and
t is an integer of 0.
21. The method according to claim 20 , wherein the isoxazoline-substituted benzamide compounds, an optically active form or the salt thereof are according to a formula
wherein,
(X) m is 3,5-Cl 2 , 3-Br, 3-I, 4-I, 3-CF 3 , 3-OCF 3 , 3,5-F 2 , 3,5-Br 2 , 3,5-(CF 3 ) 2 , 3,4-Cl 2 or 3,5-Cl 2 -4-CH 3 ,
Y is H, CH 3 , Br, CH 2 CH 3 , Cl, I or OCF 3 ,
R 1 is CH(CH 3 )CH 2 OCH 3 , 2-tetrahydrofuryl, CH 2 CF 3 , CH 2 (2-pyridyl), cyclobutyl, CH 2 CH 2 OCH 2 CH 3 , tetrahydrofurfuryl, CH 2 CH 2 SCH 2 CH 3 , CH 2 CH(CH 3 )S(O)CH 3 , CH 2 CH(CH 3 )SO 2 CH 3 , CH 2 C(O)NHCH 3 , CH 2 C(O)N(CH 3 ) 2 , CH 2 C(O)NHCH 2 CH 3 , CH 2 C(O)NH(isopropyl), CH 2 C(O)NHCH 2 CH 2 Cl, CH 2 C(O)NHCH 2 CF 3 , CH 2 C(O)NHCH 2 CH═CH 2 , CH 2 C(O)N(CH 3 )CH 2 CH═CH 2 , CH 2 C(O)NHCH 2 C≡CH, CH(CH 3 )C(O)NHCH 2 CH 2 Cl, CH 2 (4-trifluoromethylthiazol-2-yl), CH 2 (4-thiazolyl), CH 2 (2-chlorothiazol-5-yl), CH 2 (2-pyridyl), CH(CH 3 )(2-pyridyl), CH 2 (4-chloropyridin-2-yl), CH 2 (6-chloropyridin-2-yl), CH 2 (3-pyridyl), CH 2 (2-chloropyridin-5-yl), CH 2 CH 2 OCH 3 , CH 2 CH 2 CF 3 , CH(CF 3 )OCH 3 , CH(CH 3 )C(O)NHCH 2 CF 3 , CH(CH 3 )(2-thiazolyl), CH 2 OCH 3 , CH 2 OCH 2 CH 3 , CH 2 OCH 2 CH 2 CH 3 , CH 2 OCH(CH 3 ) 2 , CH 2 OCH 2 CH 2 Cl, CH 2 OCH 2 CHF 2 , CH 2 OCH 2 CF 3 , CH(CH 3 )OH, 3-tetrahydrofuryl(R), 2-tetrahydropyranyl, CH 2 SCH 3 , CH 2 S(O)CH 3 , CH 2 SO 2 CH 3 , CH 2 (2-methylthiothiazol-4-yl), 6-methoxy-2-tetrahydropyranyl or CH 2 (4-pyridyl),
R 2 is H, CH 3 , CH 2 CF 3 , C(O)CH 3 , C(O)CH 2 CH 3 , C(O)OCH 3 , C(O)O(isobutyl), C(O)OCH 2 CH 2 Cl, CH 2 CH 3 , cyclopropyl, CH 2 OCH 2 CH 3 or CH 2 OCH 3 , and
R 3 is CF 3 , CHF 2 , CF 2 Cl or CF 2 CF 3 .