Isoxazoline-substituted benzamide compound and pesticide
First Claim
1. An isoxazoline-substituted benzamide compound of formula (1) or a salt thereof:
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Accused Products
Abstract
An isoxazoline-substituted benzamide compound of formula (1) or a salt thereof:
wherein A1, A2 and A3 independently of one another are carbon atom or nitrogen atom, G is benzene ring, etc., X is halogen atom, C1-C6haloalkyl, etc., Y is halogen atom, C1-C6alkyl, etc., R1 is C1-C12alkyl arbitrarily substituted with R16, C3-C2alkenyl, arbitrarily substituted with R16 is oxygen atom or sulfur atom, —N(R20)R19, etc., R2 is hydrogen atom, C1-C4alkoxy C1-C6alkyl, etc., R3 is C1-C6haloalkyl, etc., R16 is halogen atom, cyano, phenyl substituted with (Z)p1, D-1 to D-60, E-1 to E-49, etc., R19 is phenyl, phenyl substituted with (Z)p1, etc., R20 is hydrogen atom, C1-C6alkyl, etc., Z is halogen atom, nitro, C1-C4alkoxy, etc., D-1 to D-60 are 5- or 6-membered aromatic heterocyclic rings, E-1 to E-49 are 5- or 6-membered saturated heterocyclic rings, 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.
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Citations
9 Claims
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1. An isoxazoline-substituted benzamide compound of formula (1) or a salt thereof:
- View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9)
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2. The isoxazoline-substituted benzamide compound or the salt thereof according to claim 1, wherein
G is a benzene ring; -
X is halogen atom, cyano, nitro, —
SF5, C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R4, C3-C8cycloalkyl, C3-C8cycloalkyl arbitrarily substituted with R4, C2-C6alkenyl, C2-C6alkenyl arbitrarily substituted with R4, C2-C6alkynyl, C2-C6alkynyl arbitrarily substituted with R4, —
OH, —
OR5, —
OSO2R5, —
S(O)rR5, —
C(O)OR9, —
C(O)SR9, —
C(O)NHR10, —
C(O)N(R10)R9, —
C(S)OR9, —
C(S)SR9, —
C(S)NHR10, —
C(S)N(R10)R9, —
CH═
NOR11, —
C(R9)═
NOR11, —
S(O)2NHR10, —
S(O)2N(R10)R9, —
Si(R13)(R14)R12, phenyl, phenyl substituted with (Z)p1, D-1 to D-46, E-1 to E-28, E-32 to E-38 or E-43 to E-45, when m is an integer of 2 or more, each X may be identical with or different from each other, further, when two Xs are adjacent, the adjacent two Xs may form 5-membered or 6-membered ring together with carbon atoms to which the two Xs are bonded by forming —
CH2CH2CH2—
, —
CH2CH2O—
, —
CH2OCH2—
, —
OCH2O—
, —
CH2CH2S—
, —
CH2SCH2—
, —
CH2CH2CH2CH2—
, —
CH2CH2CH2O—
, —
CH2CH2OCH2—
, —
CH2OCH2O—
, —
OCH2CH2O—
, —
OCH2CH2S—
or —
CH═
CHCH═
CH—
, in this case, hydrogen atoms bonded to each carbon atom forming the ring may be arbitrarily substituted with halogen atom, C1-C4alkyl or C1-C4haloalkyl,Y is halogen atom, cyano, nitro, C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R4, —
OR5, —
OSO2R5, —
S(O)rR5, —
NHR7, —
N(R7)R6, —
N═
CHOR8, —
N═
C(R9)OR8, —
C(O)NHR10, —
C(O)N(R10)R9, —
C(S)NHR10, —
C(S)N(R10)R9, phenyl, phenyl substituted with (Z)p1, D-1 to D-24, D-30 to D-38 or D-43 to D-46, when n is an integer of 2 or more, each Y may be identical with or different from each other,further, when two Ys are adjacent, the adjacent two Ys may form 5-membered or 6-membered ring together with carbon atoms to which the two Ys are bonded by forming —
CH2CH2CH2—
, —
CH2CH2O—
, —
CH2OCH2—
, —
OCH2O—
, —
CH2CH2CH2CH2—
, —
CH2CH2CH2O—
, —
CH2CH2OCH2—
, —
CH2OCH2O—
, —
OCH2CH2O—
, —
OCH═
N—
or —
SCH═
N—
, in this case, hydrogen atoms bonded to each carbon atom forming the ring may be arbitrarily substituted with halogen atom, C1-C4alkyl or C1-C4haloalkyl,R1 is C1-C8alkyl, C1-C8alkyl arbitrarily substituted with R16, C3-C8cycloalkyl, C3-C8halocycloalkyl, C3-C8alkenyl, C3-C8haloalkenyl, phenyl C3-C6alkenyl, phenyl C3-C6alkenyl substituted with (Z)p1, C3-C8alkynyl, C3-C8haloalkynyl, phenyl C3-C6alkynyl, phenyl C3-C6alkynyl substituted with (Z)p1, C1-C8alkoxy, —
N(R20)R19, —
N═
CHR19b, —
N═
C(R19b)R19a, —
C(O)N(R10)R9, —
C(S)N(R10)R9, —
C(═
NR11)OR9, —
C(═
NR11)SR9, —
C(═
NR11)N(R10)R9, phenyl, phenyl substituted with (Z)p1, D-1 to D-4, D-6 to D-18, D-21 to D-23, D-26 to D-40, D-42, D-45 to D-46, E-4 to E-9, E-23 to E-28, E-34 or E-45,R2 is hydrogen atom, C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl C1-C4alkyl, C1-C4alkoxy C1-C4alkyl, C1-C4haloalkoxy C1-C4alkyl, benzyloxy C1-C4alkyl, C1-C4alkylthio C1-C4alkyl, C1-C4haloalkylthio C1-C4alkyl, C1-C4alkylsulfonyl C1-C4alkyl, C1-C4haloalkylsulfonyl C1-C4alkyl, phenylthio C1-C4alkyl, phenylthio C1-C4alkyl substituted with (Z)p1, cyano C1-C6alkyl, nitro C1-C6alkyl, C1-C4alkylcarbonyl C1-C4alkyl, C1-C4alkoxycarbonyl C1-C4alkyl, C3-C6cycloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, —
SR9, —
S(O)2R9, —
SN(R18)R17, —
OH, —
OR19, —
NHR20, —
N(R20)R19, —
N═
CHR19b, —
N═
C(R19b)R19a, —
C(O)R9, —
C(O)OR9, —
C(O)SR9, —
C(S)OR9 or —
C(S)SR9;or R1 and R2 together form ═
C(R2a)R1a, and further R1 and R2 together may form 3- to 5-membered ring together with the nitrogen atom bonding them by forming C2 to C4 alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and may be arbitrarily substituted with C1-C6alkyl, formyl, C1-C6alkylcarbonyl or C1-C6alkoxycarbonyl,R1a and R2a together may form 5- or 6-membered ring together with the carbon atom bonding them by forming C4 or C5 alkylene chain or C4 or C5 alkenylene chain, in this case, the alkylene chain and the alkenylene chain may contain one to three oxygen atoms or sulfur atoms, or R1a and R2a together may form a 5-membered ring together with the carbon atom bonding them by forming C4 alkylene chain or C4 alkenylene chain, in this case, the alkylene chain and the alkenylene chain may contain one to three nitrogen atoms, and either ring may be arbitrarily substituted with halogen atom or C1-C6alkyl, R3 is cyano, C1-C6alkyl arbitrarily substituted with R4, C3-C8cycloalkyl, C3-C8halocycloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, —
OR5, —
S(O)rR5, —
N(R10)R9, —
C(O)OR9, C(O)SR9, —
C(O)NHR10, —
C(O)N(R10)R9, —
C(S)OR9, —
C(S)SR9, —
C(S)NHR10, —
C(S)N(R10)R9, —
CH═
NOR11, —
C(R9)═
NOR11, —
Si(R13)(R14)R12, phenyl, phenyl substituted with (Z)p1, D-1 to D-4, D-8 to D-13, D-15 to D-23, D-25 to D-37, D-39, D-40, D-42, D-45 to D-46 or E-4 to E-7, E-23 to E-27 or E-28;R4 is halogen atom, cyano, C3-C6cycloalkyl, C3-C6halocycloalkyl, —
OH, —
OR5, —
S(O)rR5, —
N(R10)R9, —
N(R10)C(O)R9, —
N(R10)C(O)OR9, —
N(R10)C(O)SR9, —
N(R10)C(S)OR9, —
N(R10)C(S)SR9, —
N(R10)S(O)2R9, —
Si(R13)(R14 )R12, phenyl, phenyl substituted with (Z)p1, D-1 to D-5, D-8 to D-38, D-41, D-43 or D-44;R5 is C1-C6alkyl, C1-C6haloalkyl, C1-C3haloalkoxy C1-C3haloalkyl, C3-C8cycloalkyl, C3-C8halocycloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, phenyl, phenyl substituted with (Z)p1, D-1 to D-4, D-7, D-9, D-15 to D-23, D-30 to D-35, E-3 to E-9, E-23 to E-27 or E-28 R6 is C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl C1-C4alkyl, C1-C4alkoxy C1-C4alkyl, C1-C4alkylthio C1-C4alkyl, —
S(O)2R9, —
CHO, —
C(O)R9, —
C(O)OR9, —
C(O)SR9, —
C(S)OR9 or —
C(S)SR9;R7 is hydrogen atom, C1-C6alkyl, C1-C6haloalkyl, C3-C6alkenyl or C3-C6alkynyl; R8 is C1-C6alkyl; R9 is C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl C1-C4alkyl, C1-C6alkoxy C1-C4alkyl, C1-C6alkylthio C1-C4alkyl, cyano C1-C6alkyl, phenyl C1-C4alkyl, phenyl C1-C4alkyl substituted with (Z)p1, C3-C8cycloalkyl, C3-C8halocycloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, phenyl, phenyl substituted with (Z)p1, D-1 to D-4, D-6 to D-35 or D-38; R10 is hydrogen atom or C1-C6alkyl, or R10 together with R9 may form a 5-membered ring with the nitrogen atom bonding them by forming C4alkylene chain, in this case, the alkylene chain may contain oxygen atom or sulfur atom; R11 is C1-C6alkyl, C1-C6haloalkyl, phenyl C1-C4alkyl, phenyl C1-C4alkyl substituted with (Z)p1, phenyl or phenyl substituted with (Z)p1, or R11 together with R9 may form 5- or 6-membered ring with the atom bonding them by forming C2-C3alkylene chain, in this case, the alkylene chain may be arbitrarily substituted with C1-C6alkyl; R12 is C1-C6alkyl, phenyl or phenyl substituted with (Z)p1; R13 and R14 independently of each other are C1-C6alkyl;
R15 is C1-C6alkyl, C1-C6haloalkyl, phenyl C1-C4alkyl, phenyl C1-C4alkyl substituted with (Z)p1, phenyl or phenyl substituted with (Z)p1;R16 is halogen atom, cyano, C3-C6cycloalkyl, C3-C6halocycloalkyl, —
OR25, —
N(R26)R25, —
SH, —
S(O)rR27, —
SO2NHR29, —
SO2N(R29)R28, —
CHO, —
C(O)R28, —
C(C)OR28, —
C(O)NHR29, —
C(O)N(R29)R28, —
C(O)N(R29)OR28, —
C(S)NHR29, —
C(S)N(R29)R28, —
C(R31)═
NOH, —
C(R31)═
NOR30, —
C(═
NR31)OR30, —
C(═
NR31)SR30, —
C(═
NR31)N(R29)R30, —
C(═
NOR31)NHR29, —
C(═
NOR31)N(R29)R30, —
Si(R13)(R14)R12 phenyl, phenyl substituted with (Z)p1, D-1 to D-46, E-1 to E-28, E-32 to E-38, E-43 to E-45 or M-1 to M-11;R17 is C1-C6alkyl, C1-C4alkoxy C1-C4alkyl, C1-C6alkoxycarbonyl C1-C4alkyl, phenyl C1-C4alkyl, phenyl C1-C4alkyl substituted with (Z)p1 or C1-C6alkoxycarbonyl; R18 is C1-C6alkyl, phenyl C1-C4alkyl or phenyl C1-C4alkyl substituted with (Z)p1, or R18 together with R17 may form a 5-membered ring with the nitrogen atom bonding them by forming C4alkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom, and may be arbitrarily substituted with methyl or methoxy; R19 is C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R16, C3-C6cycloalkyl, C3-C6halocycloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, —
CHO, —
C(O)R28, —
C(O)OR28, —
C(O)NHR29, —
C(O)N(R29)R28, —
C(S)NHR29, —
C(S)N(R29)R28, —
S(O)2R28, —
S(O)2NHR29, —
S(O)2N(R29)R28, phenyl, phenyl substituted with (Z)p1, D-1 to D-13, D-15 to D-25, D-30 to D-37, D-39, D-40, D-42, D-45 to D-46, E-5, E-7, E-9, E-24, E-25, E-27 or E-28;R19a is C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl, phenyl, phenyl substituted with (Z)p1, D-1 to D-4, D-8 to D-10, D-15 to D-23, E-4 to E-7, E-23 to E-27 or E-28; R19b is hydrogen atom or C1-C6alkyl, or R19a together with R19b may form 5- or 6-membered ring with the carbon atom bonding them by forming C4 or C5alkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom; R20 is hydrogen atom, C1-C6alkyl, C1-C6haloalkyl, C1-C4alkoxy C1-C4alkyl, C1-C4alkylthio C1-C4alkyl, cyano C1-C6alkyl, C1-C4alkoxycarbonyl C1-C4alkyl, C2-C6alkenyl, C3-C6alkynyl, —
CHO, —
C(O)R9, —
C(O)OR9, —
C(O)SR9, —
C(S)OR9, —
C(S)SR9 or C1-C6alkylsulfonyl;R22 is halogen atom, cyano, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6alkoxycarbonyl, —
C(O)NH2 or —
C(S)N2, when q1, q2, q3 or q4 is an integer of 2 or more, each R22 may be identical with or different from each other, further in case where two R22s are present on the same carbon atom, the two R22s together may form oxo, thioxo, imino, C1-C6alkylimino, C1-C6alkoxyimino or C1-C6alkylidene;R23 is hydrogen atom, C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R32, C3-C6cycloalkyl, C3-C6alkenyl, C3-C6alkynyl, —
OH, benzyloxy, —
CHO, —
C(O)R33, —
C(O)OR33, —
C(O)SR33, —
C(O)NHR34, —
C(O)N(R34)R33, —
S(O)2R33, phenyl, phenyl substituted with (Z)p1 or D-5;R25 is hydrogen atom, C1-C6alkyl, C1-C6haloalkyl, C1-C4alkoxy C1-C4alkyl, C1-C4alkylthio C1-C4alkyl, cyano C1-C6alkyl, phenyl C1-C4alkyl, phenyl C1-C4alkyl substituted with (Z)p1, C3-C6alkenyl, C3-C6alkynyl, —
CHO, —
C(O)R33, —
C(O)OR33, —
C(O)SR33, —
C(O)NHR34, —
C(O)N(R34)R33, —
C(S)R33, —
C(S)OR33, —
C(S)SR33, —
C(S)NHR34, —
C(S)N(R34)R33, —
S(O)2R33, —
S(O)2N(R34)R33, di(C1-C6alkyl)phosphoryl, di(C1-C6alkyl)thiophosphoryl, tri(C1-C4alkyl)silyl, phenyl or phenyl substituted with (Z)p1;R26 is hydrogen atom, C1-C6alkyl, C3-C6alkenyl, C3-C6alkynyl or C1-C6alkoxy, or R26 together with R25 may form 4- to 5-membered ring with the nitrogen atom bonding them by forming C3-C4 alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and may substituted with C1-C6alkyl, oxo or thioxo; R27 is C1-C6alklyl, C1-C6haloalkyl, hydroxy C1-C6alkyl, C1-C4alkoxy C1-C4alkyl, C1-C4alkylthio C1-C4alkyl, C1-C4alkylcarbonyl C1-C4alkyl, C1-C4alkoxycarbonyl C1-C4alkyl, di(C1-C4alkyl)aminocarbonyl C1-C4alkyl, tri(C1-C4alkyl)silyl C1-C4alkyl, phenyl C1-C4alkyl, phenyl C1-C4alkyl substituted with (Z)p1, C3-C6alkenyl, C3-C6alkynyl, C1-C6alkylcarbonyl, C1-C6alkylthio, phenylthio, phenylthio substituted with (Z)p1, —
C(O)NHR34, —
C(O)N(R34)R33, —
C(S)NHR34, —
C(S)N(R34)R33, phenyl, phenyl substituted with (Z)p1, D-21 or D-35;R28 is C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R32, C3-C6cycloalkyl, C3-C6halocycloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, phenyl, phenyl substituted with (Z)p1, D-1 to D-46 or E-1 to E-28, E-32 to E-38, or E-43 to E-545; R29 is hydrogen atom, C1-C6alkyl, C1-C4alkoxy C1-C4alkyl, C1-C4alkylthio C1-C4alkyl, cyano C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl, or R29 together with R28 may form 3- to 5-membered ring with the nitrogen atom bonding them by forming C2-C4 alkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom; R30 is C1-C6alkyl, C1-C4alkoxy C1-C4alkyl, C1-C4alkylthio C1-C4alkyl, C3-C6cycloalkyl C1-C4alkyl, tri(C1-C6alkyl)silyl C1-C4alkyl, phenyl C1-C4alkyl, phenyl C1-C4alkyl substituted with (Z)p1, C3-C8alkenyl, C3-C8haloalkenyl, C3-C8alkynyl or C3-C8haloalkynyl; R31 is hydrogen atom, C1-C6alkyl, C1-C6haloalkyl or C3-C6cycloalkyl, or R31 together with R30 may form 5- or 6-membered ring with the atom bonding them by forming C2-C3alkylene chain, in this case, the alkylene chain may be arbitrarily substituted with C1-C6alkyl; R32 is halogen atom, cyano, C3-C8cycloalkyl, C3-C8halocycloalkyl, —
OR33, —
OC(O)R33, —
OC(O)NHR33, —
OC(O)N(R34)R33, —
S(O)rR33, —
SC(O)R33, —
SC(O)NHR33, —
SC(O)N(R34)R33, —
N(R34)CHO, —
N(R34)C(O)R33, —
N(R34)C(O)OR33, —
C(O)OR33, —
C(O)NHR34, —
C(O)N(R34)R33, phenyl, phenyl substituted with (Z)p1, D-1 to D-46 or E-1 to E-28, E-32 to E-38, or E-43 to E-45;R33 is C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl C1-C4alkyl, C1-C4alkoxy C1-C4alkyl, C1-C4haloalkoxy C1-C4alkyl, C1-C4alkylthio C1-C4alkyl, C1-C4haloalkylthio C1-C4alkyl, C1-C4alkylsulfonyl C1-C4alkyl, C1-C4haloalkylsulfonyl C1-C4alkyl, cyano C1-C6alkyl, phenyl C1-C4alkyl, phenyl C1-C4alkyl substituted with (Z)p1, C3-C6cycloalkyl, C3-C6halocycloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, phenyl, phenyl substituted with (Z)p1, D-1 to D-4, D-8 to D-13, D-15 to D-18, D-21, D-29 to D-37, E-5, E-7, E-9, E-24, E-25, E-27, E-28 or E-34; R34 is hydrogen atom, C1-C6alkyl, C1-C6haloalkyl, C3-C6alkenyl or C3-C6alkynyl, or R34 together with R33 may form 3- to 5-membered ring with the nitrogen atom bonding them by forming C2-C5alkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom.
-
-
3. The isoxazoline-substituted benzamide compound or the salt thereof according to claim 2, wherein
G is a benzene ring X is halogen atom, cyano, nitro, — - SF5, C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R4, C3-C8cycloalkyl, C3-C8halocycloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, —
OR5, —
OSO2R5, —
S(O)rR5, —
C(O)OR9, —
C(O)SR9, —
C(S)OR9, —
C(S)SR9, —
C(S)NHR10, —
C(S)N(R10)R9, —
CH═
NOR11, —
C(R9)═
NOR11, —
Si(R13)(R14)R12, E-10, E-12, E-18, E-32, E-35 or E-43, when m is 2 or 3, each X may be identical with or different from each other,further, when two Xs are adjacent, the adjacent two Xs may form 5-membered or 6- membered ring together with carbon atoms to which the two Xs are bonded by forming —
CF2OCF2—
, —
OCF2O—
, —
CF2OCF2O—
or —
OCF2CF2O—
;Y is halogen atom, cyano, nitro, C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R4, —
OR5, —
OSO2R5, —
S(O)rR5, —
NHR7, —
N(R7)R6, —
N═
C(R9)OR8, —
C(O)NH2 or —
C(S)NH2, when n is 2 or 3, each Y may be identical with or different from each other;R1 is C1-C8alkyl, C1-C8alkyl arbitrarily substituted with R16, C3-C8cycloalkyl, C3-C8halocycloalkyl, C3-C8alkenyl, C3-C8haloalkenyl, C3-C8alkynyl, C3-C8haloalkynyl, —
N(R20)R19, —
C(O)N(R10)R9, —
C(S)N(R10)R9, phenyl substituted with (Z)p1, D-8 to D-18, D-21 to D-24, D-26 to D-40, D-42, D-45 to D-46, E-4, E-5, E-7, E-8, E-9, E-23 to E-25, E-27, E- 28 or E-34;R2 is hydrogen atom, C1-C6alkyl, C1-C6haloalkyl, C1-C4alkoxy C1-C4alkyl, C1-C4alkylthio C1-C4alkyl, cyano C1-C6alkyl, C3-C6cycloalkyl, C3-C6alkenyl, C3-C6alkynyl, —
OH, C1-C6alkoxy, C1-C6alkylcarbonyloxy, C1-C6alkoxycarbonyloxy, C1-C6alkylsulfonyloxy, C1-C6haloalkylthio, phenylthio, phenylthio substituted with (Z)p1, C1-C6alkylsulfonyl, —
SN(R18)R17, —
NHR20, —
N═
CHR19b, —
N═
C(R19b)R19a, —
C(O)R9, —
C(O)OR9, —
C(O)SR9, —
C(S)OR9 or —
C(S)SR9, or R2 together with R1 may form 3- to 5-membered ring with the nitrogen atom bonding them by forming C2-C4 alkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom;R3 is C1-C6haloalkyl, C3-C6cycloalkyl C1-C4alkyl, C3-C6halocycloalkyl C1-C4alkyl, C1-C4alkoxy C1-C4alkyl, C1-C4haloalkoxy C1-C4alkyl, C1-C4alkylthio C1-C4alkyl, C1-C4alkylsulfinyl C1-C4alkyl, C1-C4alkylsulfonyl C1-C4alkyl, C1-C4haloalkylthio C1-C4alkyl, C1-C4haloalkylsulfinyl C1-C4alkyl, C1-C4haloalkylsulfonyl C1-C4alkyl, cyano C1-C6alkyl, C1-C4alkoxy C1-C4haloalkyl, C1-C4haloalkoxy C1-C4haloalkyl, C1-C4alkylthio C1-C4haloalkyl, C1-C4alkylsulfinyl C1-C4haloalkyl, C1-C4alkylsulfonyl C1-C4haloalkyl, C1-C4haloalkylthio C1-C4haloalkyl, C1-C4haloalkylsulfinyl C1-C4haloalkyl, C1-C4haloalkylsulfonyl C1-C4haloalkyl, cyano C1-C6haloalkyl, C3-C8cycloalkyl, C3-C8halocycloalkyl, E-4 to E-7, E-23 to E-27 or E-28; R4 is halogen atom, cyano, —
OH, C1-C6alkoxy, C1-C6haloalkoxy, C1-C6alkylthio, C1-C6haloalkylthio, C1-C6alkylsulfinyl, C1-C6haloalkylsulfinyl, C1-C6alkylsulfonyl, C1-C6haloalkylsulfonyl or tri(C1-C6alkyl)silyl;R5 is C1-C6alkyl, C1-C6haloalkyl, C1-C3haloalkoxy C1-C3haloalkyl, C3-C8cycloalkyl, C3-C8halocycloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, E-4 to E-9, E-23 to E-27 or E-28; R6 is C1-C6alkyl, C1-C6haloalkyl, —
S(O)2R9, —
CHO, —
C(O)R9, —
C(O)OR9, —
C(O)SR9, —
C(S)OR9 or —
C(S)SR9;R7 is hydrogen atom, C1-C6alkyl or C1-C6haloalkyl; R9 is C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl C1-C4alkyl, C1-C6alkoxy C1-C4alkyl, C1-C6alkylthio C1-C4alkyl, cyano C1-C6alkyl, phenyl C1-C4alkyl, C3-C8cycloalkyl, C3-C8halocycloalkyl, C3-C6alkenyl or C3-C6alkynyl; R10 is hydrogen atom or C1-C6alkyl, or R10 together with R9 may form a 5-membered ring with the nitrogen atom bonding them by forming C4 alkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom; R11 is C1-C6alkyl or C1-C6haloalkyl, or R11 together with R9 may form 5- or 6-membered ring with the atom bonding them by forming C2 or C3alkylene chain, in this case, the alkylene chain may be arbitrarily substituted with C1-C6alkyl; R15 is C1-C6alkyl or C1-C6haloalkyl; R16 is halogen atom, cyano, C3-C6cycloalkyl, C3-C6halocycloalkyl, —
OR25, —
N(R26)R25, —
S(O)rR27, —
SO2NHR29, —
SO2N(R29)R28, —
CHO, —
C(O)R28, —
C(O)OR28, —
C(O)NHR29, —
C(O)N(R29)R28, —
C(O)N(R29)OR28, —
C(S)NHR29, —
C(S)N(R29)R28, —
C(R31)═
NOH, —
C(R31)═
NOR30, —
C(═
NR31)OR30, —
C(═
NR31)SR30, —
C(═
NR31)N(R29)R30, —
C(═
NOR31)NHR29, —
C(═
NOR31)N(R29)R30, phenyl, phenyl substituted with (Z)p1, D-1 to D-4, D-8 to D-42, E-4 to E-12, E-14, E-16 to E-19, E-21 to E-23, E-26 to E-28, E-43 to E-45, M-2, M-3, M-5 or M-8 to M-10;R17 is C1-C6alkyl, C1-C6alkoxycarbonyl C1-C4alkyl or C1-C6alkoxycarbonyl; R18 is C1-C6alkyl or benzyl; R19 is C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl C1-C6alkyl, phenyl C1-C6alkyl, phenyl C1-C6alkyl substituted with (Z)p1, C3-C6cycloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, —
C(O)R28, —
C(O)OR28, —
C(O)NHR29, —
C(O)N(R29)R28, —
C(S)NHR29, —
C(S)N(R29)R28, C1-C6alkylsulfonyl, C1-C6haloalkylsulfonyl, phenylsulfonyl, phenylsulfonyl substituted with (Z)p1, phenyl, phenyl substituted with (Z)p1, D-1 to D-4, D-18, D-21, D-25 or D-30 to D-35;R19a is C1-C6alkyl; R19b is hydrogen atom or C1-C6alkyl; R20 is hydrogen atom, C1-C6alkyl, C1-C4alkoxy C1-C4alkyl, C1-C4alkylthio C1-C4alkyl, cyano C1-C6alkyl, C3-C6alkenyl, C3-C6alkynyl, —
CHO, C1-C6alkylcarbonyl, C1-C6haloalkylcarbonyl, C1-C6alkoxycarbonyl, C1-C6haloalkoxycarbonyl or C1-C6alkylsulfonyl;R22 is C1-C4alkyl or C1-C4haloalkyl, or two R22s present on the same carbon atom may together form oxo, or thioxo; R23 is hydrogen atom, C1-C6alkyl, —
CHO, C1-C6alkylcarbonyl, C1-C6haloalkylcarbonyl, C1-C6alkoxycarbonyl, C1-C6alkylsulfonyl or C1-C6haloalkylsulfonyl,R25 is hydrogen atom, C1-C6alkyl, C1-C6haloalkyl, —
C(O)R33, —
C(O)OR33, —
C(O)SR33, —
C(O)NHR34, —
C(O)N(R34)R33, —
C(S)R33, —
C(S)OR33, —
C(S)SR33, —
C(S)NHR34, —
C(S)N(R34)R33, —
S(O)2R33, —
S(O)2N(R34)R33, di(C1-C6alkyl)thiophosphoryl, phenyl or phenyl substituted with (Z)p1;R26 is hydrogen atom or C1-C6alkyl, or R26 together with R25 may form 4- to 5-membered ring with the nitrogen atom bonding them by forming C3-C4 alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and may be substituted with C1-C6alkyl, oxo or thioxo; R27 is C1-C6alkyl, C1-C6haloalkyl, tri(C1-C4alkyl)silyl C1-4alkyl, C1-C6alkylthio, —
C(O)NHR34, —
C(O)N(R34)R33, —
C(S)NHR34, —
C(S)N(R34)R33, phenyl or phenyl substituted with (Z)p1;R28 is C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R32, C3-C6cycloalkyl, C3-C6halocycloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, phenyl or phenyl substituted with (Z)p1; R29 is hydrogen atom, C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl, or R29 together with R28 may form 3- to 5-membered ring with the nitrogen atom bonding them by forming C2-C4 alkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom; R30 is C1-C6alkyl, C3-C6cycloalkyl C1-C4alkyl, phenyl C1-C4alkyl, phenyl C1-C4alkyl substituted with (Z)p1, C3-C8alkenyl or C3-C8alkynyl; R31 is hydrogen atom or C1-C6alkyl, or R31 together with R30 may form 5- or 6-membered ring with the atom bonding them by forming C2 or C3alkylene chain, in this case, the alkylene chain may be arbitrarily substituted with C1-C6alkyl; R32 is halogen atom, cyano, C3-C6cycloalkyl, C3-C6halocycloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylthio, C1-C4haloalkylthio, C1-C4alkoxycarbonyl, —
C(O)NH2, C1-C4alkylaminocarbonyl, di(C1-C4alkyl)aminocarbonyl, phenyl or phenyl substituted with (Z)p1, R33 is C1-C6alkyl, C1-C6haloalkyl, C1-C4alkoxy C1-C4alkyl, C1-C4alkylthio C1-C4alkyl, C1-C4alkylsulfonyl C1-C4alkyl, phenyl C1-C4alkyl, phenyl C1-C4alkyl substituted with (Z)p1, C3-C6cycloalkyl, C3-C6halocycloalkyl, C3-C6alkenyl, C3-C6alkynyl, phenyl or phenyl substituted with (Z)p1;R34 is hydrogen atom or C1-C6alkyl; m is an integer of 1 to 3; n is an integer of 0 to 2; q1 is 0; q2 is an integer of 0 to 3; q3 is an integer of 0 to 2; and q4 is an integer of 0 to 2.
- SF5, C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R4, C3-C8cycloalkyl, C3-C8halocycloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, —
-
4. The isoxazoline-substituted benzamide compound or the salt thereof according to claim 3, wherein
A1 is carbon; -
A2 and A3 are carbon atom; G is a benzene ring; X is halogen atom, cyano, nitro, —
SF5, C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R4, C3-C8cycloalkyl, C3-C8halocycloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, —
OR5, —
OSO2R5, —
S(O)rR5 or tri(C1-C6alkyl)silyl, when m is 2 or 3, each X may be identical with or different from each other,further, when two Xs are adjacent, the adjacent two Xs may form 5-membered or 6-membered ring together with carbon atoms to which the two Xs are bonded by forming —
CF2OCF2—
, —
OCF2O—
, —
CF2OCF2O—
or —
OCF2CF2O—
;Y is halogen atom, cyano, nitro, C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R4, —
OR5, —
OSO2R5, —
S(O)rR5, —
NHR7, —
N(R7)R6, —
C(O)NH2 or —
C(S)NH2, when n is 2 or 3, each Y may be identical with or different from each other;R1 is C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R16, C3-C8cycloalkyl, C3-C6halocycloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, —
N(R20)R19, —
C(O)N(R10)R9, —
C(S)N(R10)R9, phenyl substituted with (Z)p1, D-8, D-10, D-11, D-13 to D-15, D-17, D-18, D-21 to D-23, D-26 to D-37, D-39, D-40, D-42, D-45, E-4, E-5, E-7 or E-9;R2 is hydrogen atom, C1-C6alkyl, C1-C4alkoxy C1-C4alkyl, C1-C4alkylthio C1-C4alkyl, cyano C1-C6alkyl, C3-C6cycloalkyl, C3-C6alkenyl, C3-C6alkynyl, —
OH, C1-C6alkylcarbonyloxy, C1-C6alkylsulfonyloxy, —
NH2, —
C(O)R9, —
C(O)OR9, —
C(O)SR9, —
C(S)OR9 or —
C(S)SR9;R3 is C1-C6haloalkyl, C1-C4alkoxy C1-C4haloalkyl, C1-C4haloalkoxy C1-C4haloalkyl, C1-C4alkylthio C1-C4haloalkyl, C1-C4haloalkylthio C1-C4haloalkyl, cyano C1-C6haloalkyl or C3-C8halocycloalkyl; R4 is halogen atom, cyano, —
OH, C1-C6alkoxy, C1-C6haloalkoxy, C1-C6alkylthio, C1-C6haloalkylthio, C1-C6alkylsulfinyl, C1-C6haloalkylsulfinyl, C1-C6alkylsulfonyl, C1-C6haloalkylsulfonyl or tri(C1-C6alkyl)silyl;R5 is C1-C6alkyl, C1-C6haloalkyl, C1-C3haloalkoxy C1-C3haloalkyl, C3-C8cycloalkyl, C3-C8halocycloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C3-C6alkynyl or C3-C6haloalkynyl; R6 is C1-C6alkyl, C1-C6haloalkyl, —
CHO, C1-C6alkylcarbonyl, C1-C6haloalkylcarbonyl, C3-C6cycloalkylcarbonyl, C3-C6halocycloalkylcarbonyl, C1-C6alkoxycarbonyl, C1-C6haloalkoxycarbonyl, C1-C6alkylthiocarbonyl, C1-C6alkoxythiocarbonyl, C1-C6alkyldithiocarbonyl, C1-C6alkylsulfonyl or C1-C6haloalkylsulfonyl;R7 is hydrogen atom or C1-C6alkyl; R9 is C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl C1-C4alkyl, C1-C6alkoxy C1-C4alkyl, C1-C6alkylthio C1-C4alkyl, cyano C1-C6alkyl, C3-C8cycloalkyl, C3-C6alkenyl or C3-C6alkynyl; R16 is halogen atom, cyano, C3-C6cycloalkyl, C3-C6halocycloalkyl, —
OR25, —
N(R26)R25, —
S(O)rR27, —
SO2NHR29, —
SO2N(R29)R28, —
C(O)R28, —
C(O)OR28, —
C(O)NHR29, —
C(O)N(R29)R28, —
C(O)N(R29)OR28, —
C(S)NHR29, —
C(S)N(R29)R28, —
C(R31)═
NOH, —
C(R31)═
NOR30, —
C(═
NR31)OR30, —
C(═
NR31)SR30, phenyl, phenyl substituted with (Z)p1, D-1 to D-4, D-8 to D-38, E-4 to E-12, E-18, E-19, E-32, E-35, E-43, M-2, M-3, M-5, M-8, M-9 or M-10;R19 is C1-C6haloalkyl, C3-C6cycloalkyl, —
C(O)R28, —
C(O)OR28, —
C(O)NHR29, —
C(O)N(R29)R28, —
C(S)NHR29, —
C(S)N(R29)R28, phenyl, phenyl substituted with (Z)p1, D-3, D-4, D-21;R20 is hydrogen atom, C1-C6alkyl, C1-C4alkoxy C1-C4alkyl, C1-C4alkylthio C1-C4alkyl, cyano C1-C6alkyl, C3-C6alkenyl, C3-C6alkynyl, —
CHO, C1-C6alkylcarbonyl, C1-C6alkoxycarbonyl or C1-C6alkylsulfonyl;R25 is C1-C6alkyl, C1-C6haloalkyl, C1-C6alkylcarbonyl, C1-C6alkoxycarbonyl, C1-C6alkylaminocarbonyl, di(C1-C6alkyl)aminocarbonyl or C1-C6alkylsulfonyl; R26 is hydrogen atom or C1-C6alkyl; R27 is C1-C6alkyl, C1-C6haloalkyl or tri(C1-C4alkyl)silyl C1-C4alkyl; R28 is C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl C1-C4alkyl, C1-C4alkoxy C1-C4alkyl, C1-C4alkylthio C1-C4alky, cyano C1-C6alkyl, phenyl C1-C4alkyl, phenyl C1-C4alkyl substituted with (Z)p1, C3-C6cycloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, phenyl or phenyl substituted with (Z)p1; R29 is hydrogen atom, C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl; R30 is C1-C6alkyl or C3-C6cycloalkyl C1-C4alkyl; R31 is hydrogen atom or C1-C6alkyl, or R31 together with R30 may form 5- or 6-membered ring with the atom bonding them by forming C2 or C3alkylene chain.
-
-
5. The isoxazoline-substituted benzamide compound or the salt thereof according to claim 4, wherein
X is halogen atom, cyano, nitro, — - SF5, C1-C6alkyl, C1-C6haloalkyl, hydroxy C1-C6haloalkyl, C1-C6alkoxy C1-C6haloalkyl, C1-C6haloalkoxy C1-C6haloalkyl, C3-C8halocycloalkyl, —
OR5, —
OSO2R5 or —
S(O)rR5, when m is 2 or 3, each X may be identical with or different from each other;Y is halogen atom, cyano, nitro, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C6alkylthio, C1-C6haloalkylthio, C1-C6alkylsulfonyl, C1-C6-C6haloalkylsulfonyl, —
NHR7 or —
N(R7)R6;R1 is C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R16, C3-C6cycloalkyl, C3-C6alkenyl, C3-C8haloalkenyl, C3-C6alkynyl, —
N(R20)R19, D-8, D-10, D-13 to D-15, D-18, D-21, D-34, D-35;R2 is hydrogen atom, C1-C6alkyl, C1-C4alkoxy C1-C4alkyl, cyano C1-C6alkyl, C3-C6alkynyl, —
C(O)R9 or —
C(O)OR9;R3 is C1-C6haloalkyl or C3-C8halocycloalkyl; R5 is C1-C6alkyl, C1-C6haloalkyl or C1-C3haloalkoxy C1-C3haloalkyl; R6 is C1-C6alkyl, —
CHO, C1-C6alkylcarbonyl, C1-C6haloalkylcarbonyl, C1-C6alkoxycarbonyl, C1-C6alkylthiocarbonyl, C1-C6alkoxythiocarbonyl, C1-C6alkyldithiocarbonyl, C1-C6alkylsulfonyl or C1-C6haloalkylsulfonyl;R9 is C1-C6alkyl, C1-C6alkoxy C1-C4alkyl, C1-C6alkylthio C1-C4alkyl, C3-C8cycloalkyl, C3-C6alkenyl or C3-C6alkynyl; R16 is halogen atom, cyano, C3-C6cycloalkyl, C3-C6halocycloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, C1-C6alkylthio, C1-C6haloalkylthio, C1-C6alkylsulfinyl, C1-C6haloalkylsulfinyl, C1-C6alkylsulfonyl, C1-C6haloalkylsulfonyl, C1-C6alkylcarbonyl, —
C(O)OR28, —
C(O)NHR29, —
C(O)N(R29)R28, —
C(S)NH2, —
C(R31)═
NOH, —
C(R31)═
NOR30, phenyl, phenyl substituted with (Z)p1, D-1 to D-4, D-8 to D-38, E-4 to E-7, E-10, E-11 or E-32;R19 is C1-C6haloalkyl, —
C(O)R29, —
C(O)OR28, phenyl, phenyl substituted with (Z)p1, D-3, D-4, D-21;R20 is hydrogen atom or C1-C6alkyl; R28 is C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl C1-C4alkyl, C3-C6cycloalkyl, C3-C6alkenyl or C3-C6alkynyl; R29 is hydrogen atom or C1-C6alkyl; R30 is C1-C6alkyl; R31 is hydrogen atom or C1-C6alkyl; and n is an integer of 0 or 1.
- SF5, C1-C6alkyl, C1-C6haloalkyl, hydroxy C1-C6haloalkyl, C1-C6alkoxy C1-C6haloalkyl, C1-C6haloalkoxy C1-C6haloalkyl, C3-C8halocycloalkyl, —
-
6. A pesticide containing as an active ingredient one or more selected from isoxazoline-substituted benzamide compound and the salt thereof according to claim 1.
-
7. An agrochemical containing as an active ingredient one or more selected from isoxazoline-substituted benzamide compound and the salt thereof according to claim 1.
-
8. An endo- or ecto-parasiticide for mammals or birds containing as an active ingredient one or more selected from isoxazoline-substituted benzamide compound and the salt thereof according to claim 1.
-
9. An insecticide or acaricide containing as an active ingredient one or more selected from isoxazoline-substituted benzamide compound and the salt thereof according to claim 1.
-
2. The isoxazoline-substituted benzamide compound or the salt thereof according to claim 1, wherein
Specification
- Resources
-
Current AssigneeNissan Chemical Corporation
-
Original AssigneeNissan Chemical Industries Limited (Nissan Chemical Corporation)
-
InventorsYaosaka, Manabu, Mizukoshi, Takashi, Mita, Takeshi, Komoda, Mitsuaki, Kikuchi, Takamasa
-
Primary Examiner(s)Anderson; Rebecca L
-
Assistant Examiner(s)JACKSON, SHAWQUIA
-
Application NumberUS11/514,921Publication NumberTime in Patent Office1,260 DaysField of Search548/240US Class Current548/240CPC Class CodesA01N 43/80 five-membered rings with on...A61K 31/421 1,3-Oxazoles, e.g. pemoline...A61K 9/0053 Mouth and digestive tract, ...A61P 33/04 AmoebicidesA61P 33/06 AntimalarialsA61P 33/10 AnthelminticsA61P 33/12 SchistosomicidesA61P 33/14 Ectoparasiticides, e.g. sca...C07C 205/11 having nitro groups bound t...C07C 205/12 the six-membered aromatic r...C07C 211/52 the carbon skeleton being f...C07C 25/02 Monocyclic aromatic halogen...C07C 25/06 Monochloro-benzeneC07C 25/08 Dichloro-benzenesC07C 25/13 containing fluorineC07C 25/24 Halogenated aromatic hydroc...C07C 251/48 with the carbon atom of at ...C07C 255/29 containing cyano groups and...C07C 255/50 to carbon atoms of non-cond...C07C 255/60 at least one of the singly-...C07C 281/02 : Compounds containing any of...C07C 323/09 : having sulfur atoms of thio...C07C 43/1742 : with halogen atoms bound to...C07C 43/1745 : having more than one ether ...C07D 261/04 : having one double bond betw...C07D 261/16 : Benzene-sulfonamido isoxazolesC07D 413/04 : directly linked by a ring-m...C07D 413/06 : linked by a carbon chain co...C07D 413/12 : linked by a chain containin...C07D 413/14 : containing three or more he...C07D 417/06 : linked by a carbon chain co...C07D 417/12 : linked by a chain containin...C07F 7/0812 : comprising a heterocyclic ring