Isoxazoline-substituted benzamide compound and pesticide
An isoxazoline-substituted benzamide compound of formula (1) or a salt thereof: wherein A 1 , A 2 and A 3 independently of one another are carbon atom or nitrogen atom, G is benzene ring, etc., W is oxygen atom or sulfur atom, etc., X is halogen atom, C 1 -C 6 haloalkyl, etc., Y is halogen atom, C 1 -C 6 alkyl, etc., R 1 is —CH═NOR 1a , —C(O)OR 1c , —C(O)NHR 1d , phenyl substituted with (Z) p1 , D-14, D-52, D-53, D-55 to D-59, etc., R 1a is C 1 -C 6 alkyl, etc., R 1c is C 1 -C 6 alkyl, etc., R 1d is hydrogen atom, —C(O)R 15 , —C(O)OR 15 , etc., R 2 is C 1 -C 6 alkyl, —CH 2 R 14a , C 1 -C 6 alkynyl, —C(O)R 15 , —C(O)OR 15 , etc., further when R 1 is —CH═NOR 1a , —C(O)OR 1c or —C(O)N(R 1e )R 1d , R 2 may be hydrogen atom, R 3 is C 1 -C 6 haloalkyl, etc., R 14a is cyano, —OR 25 , etc., R 15 is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 4 alkoxy C 1 -C 4 alkyl, C 1 -C 4 alkylthio C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, C 2 -C 6 alkenyl, etc., R 25 is C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, —C(O)R 32 or —C(O)OR 32 , etc., R 32 is C 1 -C 6 alkyl or C 3 -C 6 cycloalkyl, etc., Z is halogen atom, cyano, nitro, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, etc., m is an integer of 0 to 5, n is an integer of 0 to 4, p1 is an integer of 1 to 5. The pesticide containing these compounds.
1. 4-Hydroxyiminomethyl substituted benzamide compound of formula (2) or a salt thereof:
wherein
A 1 is carbon atom or nitrogen atom,
J is hydrogen atom or halogen atom,
W is oxygen atom or sulfur atom,
Y is halogen atom, cyano, nitro, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 4 alkyl arbitrarily substituted with R 4 , —OR 5 , —N(R 7 )R 6 or —C(S)NH 2 , when n is 2, each Y may be identical with or different from each other,
R 1 is —C(R 1b )=NOR 1a , —C(O)OR 1c , —C(O)SR 1c , —C(S)OR 1c , —C(O)N(R 1e )R 1d , —C(S)N(R 1e )R 1d , phenyl, phenyl substituted with (Z) p1 , D-3, D-8, D-10, D-11, D-13 to D-15, D-17, D-22, D-35, D-52 to D-58 or D-59,
R 1a is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 8 cycloalkyl C 1 -C 4 alkyl, C 3 -C 6 alkenyl or C 3 -C 6 alkynyl,
R 1b is hydrogen atom or C 1 -C 6 alkyl,
R 1c is C 1 -C 6 alkyl, C 1 -C 4 alkyl arbitrarily substituted with R 14 or C 3 -C 6 cycloalkyl,
R 1d is hydrogen atom, —C(O)R 15 , —C(O)OR 15 or —C(O)SR 15 ,
R 1e is hydrogen atom or C 1 -C 6 alkyl,
R 2 is C 1 -C 6 alkyl, —CH 2 R 14a , E-5, E-24, C 3 -C 6 alkynyl, —C(O)R 15 , —C(O)OR 15 , —C(O)SR 15 , —C(S)OR 15 , —C(S)SR 15 , —C(O)C(O)OR 15 , phenyl or phenyl substituted with (Z) p1 , further when R 1 is —C(R 1b )=NOR 1a , —C(O)OR 1c , —C(O)SR 1c , —C(S)OR 1c , —C(O)N(R 1e )R 1d or —C(S)N(R 1e )R 1d , R 2 may be hydrogen atom, when R 1 is phenyl, phenyl substituted with (Z) p1 , D-3, D-8, D-10, D-11, D-13 to D-15, D-17, D-22, D-35, D-52 to D-58 or D-59, R 2 may be C 1 -C 6 haloalkyl or C 3 -C 6 alkenyl,
or R 2 together with R 1 may form ═C(R 2b )R 2a ,
R 2a is C 1 -C 6 alkoxy or di(C 1 -C 6 alkyl)amino,
R 2b is C 1 -C 6 alkyl or C 1 -C 6 alkylcarbonylthio,
D-3, D-8, D-10, D-11, D-13 to D-15, D-17, D-22, D-35, D-52 to D-58 and D-59 are aromatic heterocyclic rings of the following formulae, respectively
Z is halogen atom, cyano, nitro, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylsulfonyloxy, C 1 -C 6 haloalkylsulfonyloxy, 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 alkoxycarbonyl, —C(O)NH 2 or —C(S)NH 2 , when p1, p2 or p3 is an integer of 2 or more, each Z may be identical with or different from each other, further, when two Zs are adjacent, the adjacent two Zs may form 5-membered or 6-membered ring together with carbon atoms to which the two Zs are bonded by forming —OCH 2 O— or —OCH 2 CH 2 O—, in this case, hydrogen atoms bonded to each carbon atom forming the ring may be arbitrarily substituted with halogen atom, E-5 and E-24 are saturated heterocyclic rings of the following formulae, respectively,
R 4 is C 1 -C 6 alkoxy or C 1 -C 6 haloalkoxy,
R 5 is C 1 -C 6 alkyl or C 1 -C 6 haloalkyl,
R 6 is —CHO, C 1 -C 6 alkylcarbonyl, C 1 -C 6 haloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylthiocarbonyl, C 1 -C 6 alkoxythiocarbonyl, C 1 -C 6 alkyldithiocarbonyl, C 1 -C 6 alkylsulfonyl or C 1 -C 6 haloalkylsulfonyl,
R 7 is hydrogen atom or C 1 -C 6 alkyl
R 13 is C 1 -C 6 alkyl or C 1 -C 6 haloalkyl,
R 14 is cyano, C 3 -C 6 cycloalkyl, C 1 -C 6 alkoxy, C 1 -C 4 alkoxy, C 1 -C 6 alkylsulfonyl, —NHC(O)R 32 , —NHC(O)OR 32 , C 1 -C 6 alkylcarbonyl or C 1 -C 6 alkoxycarbonyl,
R 14a is cyano, —OR 25 , —NHC(O)OR 32 , —S(O) r R 27 , C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl or phenyl,
R 15 is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 4 alkyl arbitrarily substituted with R 31 , C 3 -C 6 cycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, phenyl, phenyl substituted with (Z) p1 , D-52, D-53 or D-54,
R 25 is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 4 alkoxy C 1 -C 4 alkyl, benzyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, —C(O)R 32 or —C(O)OR 32 ,
R 27 is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C(O)R 32 or —C(S)OR 32 ,
R 31 is C 3 -C 6 cycloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylsulfonyl or phenyl,
R 32 is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl or phenyl,
n is an integer of 0 to 2,
p1 is an integer of 1 to 3,
p2 and p3 are an integer of 0 to 2,
p4 and p5 are an integer of 0 or 1,
q3 and q4 are 0,
r is an integer of 0 or 2, and
t is an integer of 0 or 1.
2. 4-Hydroxyiminomethyl substituted benzamide compound or the salt thereof according to claim 1 , wherein
A 1 is carbon atom,
W is oxygen atom,
Y is halogen atom, cyano, nitro, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, —OR 5 or —N(R 7 )R 6 ,
R 1 is —CH═NOR 1a ,
R 1a is C 1 -C 6 alkyl,
R 2 is hydrogen atom, —CH 2 R 14a , C 3 -C 6 alkynyl or C 1 -C 6 alkoxycarbonyl,
R 5 is C 1 -C 6 alkyl or C 1 -C 6 haloalkyl,
R 6 is —CHO, C 1 -C 6 alkylcarbonyl or C 1 -C 6 alkoxycarbonyl,
R 14a is cyano or —OR 25 ,
R 25 is C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or —C(O)OR 32 , and
R 32 is C 1 -C 6 alkyl.
3. 4-Hydroxyiminomethyl substituted benzamide compound or the salt thereof according to claim 1 , wherein
A 1 is carbon atom,
W is oxygen atom,
Y is halogen atom, cyano, nitro, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, —OR 5 or —N(R 7 )R 6 ,
R 1 is —C(O)OR 1c ,
R 1c is C 1 -C 6 alkyl or C 3 -C 6 cycloalkyl,
R 2 is hydrogen atom, C 1 -C 6 alkyl, —CH 2 R 14a , E-5, —C(O)R 15 , C 1 -C 6 alkoxycarbonyl, C 1 -C 6 haloalkoxycarbonyl or C 1 -C 6 haloalkylthio,
R 5 is C 1 -C 6 alkyl or C 1 -C 6 haloalkyl,
R 6 is —CHO, C 1 -C 6 alkylcarbonyl or C 1 -C 6 alkoxycarbonyl,
R 14a is cyano, —OR 25 , or —NHC(O)0R 32 ,
R 15 is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 4 alkoxy C 1 -C 4 alkyl, C 1 -C 4 alkylthio C 1 -C 4 alkyl or C 3 -C 6 cycloalkyl,
R 25 is C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or —C(O)OR 32 ,
R 32 is C 1 -C 6 alkyl,
n is an integer of 0 or 1, and
q3 is 0.
4. 4-Hydroxyiminomethyl substituted benzamide compound or the salt thereof according to claim 1 , wherein
A 1 is carbon atom,
W is oxygen atom,
Y is halogen atom, cyano, nitro, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, —OR 5 or —N(R 7 )R 6 ,
R 1 is —C(O)N(R 1e )R 1d ,
R 1d is hydrogen atom, —C(O)R 15 or —C(O)OR 15 ,
R 1e is hydrogen atom or C 1 -C 6 alkyl,
R 2 is hydrogen atom or C 1 -C 6 alkyl,
R 5 is C 1 -C 6 alkyl or C 1 -C 6 haloalkyl,
R 6 is —CHO, C 1 -C 6 alkylcarbonyl or C 1 -C 6 alkoxycarbonyl,
R 15 is C 1 -C 6 alkyl or C 1 -C 6 haloalkyl, and
n is an integer of 0 or 1.
5. 4-Hydroxyiminomethyl substituted benzamide compound or the salt thereof according to claim 1 , wherein
A 1 is carbon atom,
W is oxygen atom,
Y is halogen atom, cyano, nitro, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, —OR 5 or —N(R 7 )R 6 ,
R 1 is phenyl substituted with (Z) p1 , D-52, D-55, D-56, D-57 or D-58,
R 2 is C 1 -C 6 alkyl, —CH 2 R 14a , C 3 -C 6 alkynyl, —C(O)R 15 , —C(O)OR 15 or —C(O)C(O)OR 15 ,
Z is halogen atom, cyano, nitro, 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 alkylsulfinyl or C 1 -C 6 alkylsulfonyl, when p1, p2 or p3 is an integer of 2 or more, each Z may be identical with or different from each other,
R 5 is C 1 -C 6 alkyl or C 1 -C 6 haloalkyl,
R 6 is —CHO, C 1 -C 6 alkylcarbonyl or C 1 -C 6 alkoxycarbonyl,
R 14a is cyano or —OR 25 ,
R 15 is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 4 alkoxy C 1 -C 4 alkyl, C l -C 4 alkylthio C 1 -C 4 alkyl, C 1 -C 4 alkylsulfinyl C 1 -C 4 alkyl, C 1 -C 4 alkylsulfonyl C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, phenyl, phenyl substituted with (Z) p1 or D-52,
R 25 is C 1 -C 4 alkyl, haloalkyl, —C(O)R 32 or —C(O)OR 32 ,
R 32 is C 1 -C 6 alkyl or C 3 -C 6 cycloalkyl,
n is an integer of 0 or 1, and
t is 0.