Heterocyclic dicarboxylic acid diamide derivatives, agricultural/horticultural insecticides and method of using the same
First Claim
Patent Images
1. A heterocyclic dicarboxylic acid diamide derivative represented by the formula (I):
-
{wherein R1, R2 and R3, which may be the same or different, are hydrogen atoms, (C3-C6)cycloalkyl groups, halo(C3-C6)cycloalkyl groups or —
A1—
(R4)r (wherein A1 is a (C1-C8)alkylene group, a (C3-C6)alkenylene group or a (C3-C6)alkynylene group, R4, which may be the same or different, are hydrogen atoms;
halogen atoms;
cyano groups;
nitro groups;
halo(C1-C6)alkyl groups;
(C3-C6)cycloalkyl groups;
halo(C3-C6)cycloalkyl groups;
(C1-C6)alkoxycarbonyl groups;
di(C1-C6)alkoxyphosphoryl groups whose (C1-C6)alkoxy groups may be the same or different;
di(C1-C6)alkoxythiophosphoryl groups whose (C1-C6)alkoxy groups may be the same or different;
diphenylphosphino groups;
diphenylphosphono groups;
phenyl groups;
substituted phenyl groups having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups;
heterocyclic groups;
substituted heterocyclic groups having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups;
or —
A2—
R5 (wherein A2 is —
O—
, —
S—
, —
SO—
, —
SO2—
, —
N(R6)—
(wherein R is a hydrogen atom;
a (C1-C6)alkylcarbonyl group;
a halo(C1-C6)alkylcarbonyl group;
a (C1-C6)alkoxycarbonyl group;
a phenylcarbonyl group;
a substituted phenylcarbonyl group having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups;
a phenyl(C1-C4)alkoxycarbonyl group;
a substituted phenyl(C1-C4)alkoxycarbonyl group having on the ring one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups;
a (C1-C6)alkylsulfonyl group;
or a halo(C1-C6)alkylsulfonyl group), —
C(═
O)—
or —
C(═
NOR7)—
(wherein R7 is a hydrogen atom;
a (C1-C6)alkyl group;
a halo(C1-C6)alkyl group;
a (C3-C6)alkenyl group;
a halo(C3-C6)alkenyl group;
a (C3-C6)alkynyl group;
a cyclo(C3-C6)alkyl group;
a phenyl(C1-C4)alkyl group;
or a substituted phenyl(C1-C4)alkyl group having on the ring one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups), and R5 is a hydrogen atom;
a (C1-C6)alkyl group;
a halo(C1-C6)alkyl group;
a (C3-C6)alkenyl group;
a halo(C3-C6)alkenyl group;
a (C3-C6)alkynyl group;
a halo(C3-C6)alkynyl group;
a (C3-C6)cycloalkyl group;
a halo(C3-C6)cycloalkyl group;
a (C1-C6)alkoxy(C1-C6)alkyl group;
a (C1-C6)alkylthio(C1-C6)alkyl group;
a formyl group;
a (C1-C6)alkylcarbonyl group;
a halo(C1-C6)alkylcarbonyl group;
a (C1-C6)alkoxycarbonyl group;
a mono(C1-C6)alkylaminocarbonyl group;
a di(C1-C6)alkylaminocarbonyl group whose (C1-C6)alkyl groups may be the same or different;
a mono(C1-C6)alkylaminothiocarbonyl group;
a di(C1-C6)alkylaminothiocarbonyl group whose (C1-C6)alkyl groups may be the same or different;
a di(C1-C6)alkoxyphosphoryl group whose (C1-C6)alkoxy groups may be the same or different;
a di(C1-C6)alkoxythiophosphoryl group whose (C1-C6)alkoxy groups may be the same or different;
a phenyl group;
a substituted phenyl group having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C5)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups;
a phenyl(C1-C4)alkyl group;
a substituted phenyl(C1-C4)alkyl group having on the ring one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups;
a heterocyclic group;
or a substituted heterocyclic group having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups), and r is an integer of 1 to
4),provided that R1 and R2 are not hydrogen atoms at the same time, R1 and R2 together with the N to which they are attached may form a 4 to 7 membered ring by combining to each other, in which the ring may contain the same or different 1 to 3 hetero atoms selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom, Het is a heterocyclic group represented by any of the following formulas Q1 to Q4;
(wherein X, which may be the same or different, are halogen atoms;
cyano groups;
nitro groups;
(C3-C6)cycloalkyl groups;
halo(C3-C6)cycloalkyl groups;
tri(C1-C6)alkylsilyl groups whose (C1-C6)alkyl groups may be the same or different;
phenyl groups;
substituted phenyl groups having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups;
heterocyclic groups;
substituted heterocyclic groups having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups;
or —
A3—
R8
wherein A3 is —
O—
, —
S—
, —
SO—
, —
SO2—
, —
N(R6)—
(wherein R6 is as defined above), —
C(═
O)—
, —
C(═
NOR7)—
(wherein R7 is as defined above), a (C1-C6)alkylene group, a halo(C1-C6)alkylene group, a (C2-C6)alkenylene group, a halo(C2-C6)alkenylene group, a (C2-C6)alkynylene group or a halo(C3-C6)alkynylene group, and R8 is as follows;
(1) when A3 is —
O—
, —
S—
, —
SO—
, —
SO2—
or —
N(R6)—
(wherein R6 is as defined above), then R8 is a halo(C3-C6)cycloalkyl group;
a halo(C3-C6)cycloalkenyl group;
a phenyl group;
a substituted phenyl group having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups;
a heterocyclic group;
a substituted heterocyclic group having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups;
or —
A4—
R9 (wherein A4 is a (C1-C6)alkylene group, a halo(C1-C6)alkylene group, a (C3-C6)alkenylene group, a halo(C3-C6)alkenylene group, a (C3-C6)alkynylene group or a halo(C3-C6)alkynylene group, and R9 is a hydrogen atom;
a halogen atom;
a (C3-C6)cycloalkyl group;
a halo(C3-C6)cycloalkyl group;
a (C1-C6)alkoxycarbonyl group;
a phenyl group;
a substituted phenyl group having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups;
or —
A5—
R10 (wherein A5 is —
O—
, —
S—
, —
SO—
, —
SO2—
or —
C(═
O), and R10 is a (C1-C6)alkyl group;
a halo(C1-C6)alkyl group;
a (C3-C6)alkenyl group;
a halo(C3-C6)alkenyl group;
a (C3-C6)cycloalkyl group;
a halo(C3-C6)cycloalkyl group;
a phenyl group;
a substituted phenyl group having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups;
a heterocyclic group;
or a substituted heterocyclic group having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups)), (2) when A3 is —
C(═
O)—
or —
C(═
NOR7)—
(wherein R7 is as defined above), then R8 is a hydrogen atom;
a (C1-C6)alkyl group;
a halo(C1-C6)alkyl group;
a (C2C6)alkenyl group;
a halo(C2C6)alkenyl group;
a (C3-C6)cycloalkyl group;
a halo(C3-C6)cycloalkyl group;
a (C1-C6)alkoxy group;
a (C1-C6)alkylthio group;
a mono(C1-C6)alkylamino group;
a di(C1-C6)alkylamino group whose (C1-C6)alkyl groups may be the same or different;
a phenyl group;
a substituted phenyl group having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups;
a phenylamino group;
a substituted phenylamino group having on the ring one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups;
a heterocyclic group;
or a substituted heterocyclic group having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups, and (3) when A3 is a (C1-C6)alkylene group, a halo(C1-C6)alkylene group, a (C2-C6)alkenylene group, a halo(C2-C6)alkenylene group, a (C2-C6)alkynylene group or a halo(C3-C6)alkynylene group, then R8 is a hydrogen atom;
a halogen atom;
a (C3-C6)cycloalkyl group;
a halo(C3-C6)cycloalkyl group;
a (C1-C6)alkoxycarbonyl group;
a tri(C1-C6)alkylsilyl group whose (C1-C6)alkyl groups may be the same or different;
a phenyl group;
a substituted phenyl group having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups;
a heterocyclic group;
a substituted heterocyclic group having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups;
or —
A—
R11 (wherein A6 is —
O—
, —
S—
, —
SO—
or —
SO2—
, and R11 is a (C3-C6)cycloalkyl group;
a halo(C3-C6)cycloalkyl group;
a phenyl group;
a substituted phenyl group having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups;
a heterocyclic group;
a substituted heterocyclic group having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups;
or —
A7—
R12 (wherein A7 is a (C1-C6)alkylene group, a halo(C1-C6)alkylene group, a (C2-C6)alkenylene group, a halo(C2-C6)alkenylene group, a (C2-C6)alkynylene group or a halo(C3-C6)alkynylene group, and R12 is a hydrogen atom;
a halogen atom;
a (C3-C6)cycloalkyl group;
a halo(C3-C6)cycloalkyl group;
a (C1-C6)alkoxy group;
a halo(C1-C6)alkoxy group;
a (C1-C6)alkylthio group;
a halo(C1-C6)alkylthio group;
a (C1-C6)alkylsulfinyl group;
a halo(C1-C6)alkylsulfinyl group;
a (C1-C6)alkylsulfonyl group;
a halo(C1-C6)alkylsulfonyl group;
a phenyl group;
a substituted phenyl group having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups;
a phenoxy group;
a substituted phenoxy group having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C8)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C5)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups;
a phenylthio group;
a substituted phenylthio group having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups;
a heterocyclic group;
or a substituted heterocyclic group having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups))
, and n is an integer of 0 to 3, X may form a condensed ring selected from the group consisting of indole ring, benzo[b]furan ring, benzo[b]thiophene ring, quinoline ring, isoquinoline ring, naphthyridine ring, quinoxaline ring and cinnoline ring, by combining together with the adjacent atoms in the heterocyclic ring, and said condensed ring may have one or more substituents, which may be the same or different, and are selected from halogen atoms;
(C1-C6)alkyl groups;
halo(C1-C6)alkyl groups;
(C1-C6)alkoxy groups;
halo(C1-C6)alkoxy groups;
(C1-C6)alkylthio groups;
halo(C1-C6)alkylthio groups;
(C1-C6)alkylsulfinyl groups;
halo(C1-C6)alkylsulfinyl groups;
(C1-C6)alkylsulfonyl groups;
halo(C1-C6)alkylsulfonyl groups;
phenyl group;
substituted phenyl groups having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups;
heterocyclic groups; and
substituted heterocyclic groups having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups, W is O, S or N—
R13 (wherein R13 is a (C1-C6)alkyl group;
a halo(C1-C6)alkyl group;
a (C3-C6)alkenyl group;
a halo(C3-C6)alkenyl group;
a (C3-C6)alkynyl group;
a halo(C3-C6)alkynyl group;
a (C1-C6)alkoxy group;
a phenyl group;
a substituted phenyl group having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups;
a phenyl(C1-C6)alkyl group;
or a substituted phenyl(C1-C6)alkyl group having on the ring one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups), and p and q, which may be the same or different, are integers of 0 to
1), B1, B2, B3 and B4, which may be the same or different, are carbon atoms, Y, which may be the same or different, are halogen atoms;
cyano groups;
nitro groups;
halo(C3-C6)cycloalkyl groups;
phenyl groups;
substituted phenyl groups having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups;
heterocyclic groups;
substituted heterocyclic groups having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups;
or —
A3—
R3 (wherein A3 and R8 are as defined above), and m is an integer of 1 to 5, Y may form a condensed ring by combining together with the adjacent carbon atoms in the aromatic ring, and said condensed ring may have one or more substituents, which may be the same or different, and are selected from halogen atoms;
(C1-C6)alkyl groups;
halo(C1-C6)alkyl groups;
(C1-C6)alkoxy groups;
halo(C1-C6)alkoxy groups;
(C1-C6)alkylthio groups;
halo(C1-C6)alkylthio groups;
(C1-C6)alkylsulfinyl groups;
halo(C1-C6)alkylsulfinyl groups;
(C1-C6)alkylsulfonyl groups;
halo(C1-C6)alkylsulfonyl groups;
phenyl group;
substituted phenyl groups having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups;
heterocyclic groups; and
substituted heterocyclic groups having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups, and each of Z1 and Z2 is an oxygen atom or a sulfur atom, provided that;
(1) when Het is Q2, and B1, B2, B3 and B4 are carbon atoms at the same time, then Ym is other than 3-chloro-2-methyl group, 3-chloro-2,6-diethyl group, 5chloro-2-methyl group, 2,6-diethyl group, 4-chloro-2-fluoro group and 2-ethyl-6-methyl group, and (2) when Het is Q4 and B1, B2, B3 and B4 are carbon atoms at the same time, then Ym is other than 2,5-dichloro group, 2,4-difluoro group, 2,6-difluoro group, 3-chloro-2-methyl group, 5-chloro-2-methyl group, 5-fluoro-2-methyl group, 2,6-dimethyl group, 2,6-diethyl group, 2-ethyl-6-methyl group, 2-methoxy-5-nitro group, 2-methoxy-5methyl group, 2,6-diethoxy group, 3-bromo-2-methyl group, 3-fluoro-2-methyl group, 3-iodo-2-methyl group, 3-cyano-2-methyl group, 3-difluoromethoxy-2-methyl group, 5-chloro-2-ethyl group, 2,5-dimethyl group, 2,3-dichloro group, 3-chloro2,6-diethyl group, 4-trifluoromethyl group, 3-methoxycarbonyl-2-methyl group, 3-trifluoromethyl-2-methyl group, 3,5-dichloro-2,6diethyl group, 3,4-dichloro group, 3-(methoxycarbonylmethyloxy)-2-methyl group, 2-methyl-3-nitro group and 4-trifluoromethoxy group.
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Accused Products
Abstract
Heterocyclic dicarboxylic acid diamide derivative represented by the general formula (I):
wherein R1, R2 and R3 represent each H, optionally halogenated C3-6 cycloalkyl, etc.; Het represents a 5- or 6-membered heterocycle; X and Y represent each halocyano, nitro, optionally halogenated C3-6, cycloalkyl, optionally substituted phenyl, an optionally substituted heterocycle, etc; n is from 0 to 3; m is from 1 to 5; Z1 and Z2 represent each O or S; and B1 to B4 represent each C or N. Agricultural/horticultural insecticides having an excellent controlling effect on pest insects such as diamond-back moth (Pluntella xylostella) and tobacco cutworm (Spodoptera litura).
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Citations
7 Claims
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1. A heterocyclic dicarboxylic acid diamide derivative represented by the formula (I):
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{wherein R1, R2 and R3, which may be the same or different, are hydrogen atoms, (C3-C6)cycloalkyl groups, halo(C3-C6)cycloalkyl groups or —
A1—
(R4)r (wherein A1 is a (C1-C8)alkylene group, a (C3-C6)alkenylene group or a (C3-C6)alkynylene group, R4, which may be the same or different, are hydrogen atoms;
halogen atoms;
cyano groups;
nitro groups;
halo(C1-C6)alkyl groups;
(C3-C6)cycloalkyl groups;
halo(C3-C6)cycloalkyl groups;
(C1-C6)alkoxycarbonyl groups;
di(C1-C6)alkoxyphosphoryl groups whose (C1-C6)alkoxy groups may be the same or different;
di(C1-C6)alkoxythiophosphoryl groups whose (C1-C6)alkoxy groups may be the same or different;
diphenylphosphino groups;
diphenylphosphono groups;
phenyl groups;
substituted phenyl groups having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups;
heterocyclic groups;
substituted heterocyclic groups having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups;
or —
A2—
R5 (wherein A2 is —
O—
, —
S—
, —
SO—
, —
SO2—
, —
N(R6)—
(wherein R is a hydrogen atom;
a (C1-C6)alkylcarbonyl group;
a halo(C1-C6)alkylcarbonyl group;
a (C1-C6)alkoxycarbonyl group;
a phenylcarbonyl group;
a substituted phenylcarbonyl group having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups;
a phenyl(C1-C4)alkoxycarbonyl group;
a substituted phenyl(C1-C4)alkoxycarbonyl group having on the ring one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups;
a (C1-C6)alkylsulfonyl group;
or a halo(C1-C6)alkylsulfonyl group), —
C(═
O)—
or —
C(═
NOR7)—
(wherein R7 is a hydrogen atom;
a (C1-C6)alkyl group;
a halo(C1-C6)alkyl group;
a (C3-C6)alkenyl group;
a halo(C3-C6)alkenyl group;
a (C3-C6)alkynyl group;
a cyclo(C3-C6)alkyl group;
a phenyl(C1-C4)alkyl group;
or a substituted phenyl(C1-C4)alkyl group having on the ring one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups), and R5 is a hydrogen atom;
a (C1-C6)alkyl group;
a halo(C1-C6)alkyl group;
a (C3-C6)alkenyl group;
a halo(C3-C6)alkenyl group;
a (C3-C6)alkynyl group;
a halo(C3-C6)alkynyl group;
a (C3-C6)cycloalkyl group;
a halo(C3-C6)cycloalkyl group;
a (C1-C6)alkoxy(C1-C6)alkyl group;
a (C1-C6)alkylthio(C1-C6)alkyl group;
a formyl group;
a (C1-C6)alkylcarbonyl group;
a halo(C1-C6)alkylcarbonyl group;
a (C1-C6)alkoxycarbonyl group;
a mono(C1-C6)alkylaminocarbonyl group;
a di(C1-C6)alkylaminocarbonyl group whose (C1-C6)alkyl groups may be the same or different;
a mono(C1-C6)alkylaminothiocarbonyl group;
a di(C1-C6)alkylaminothiocarbonyl group whose (C1-C6)alkyl groups may be the same or different;
a di(C1-C6)alkoxyphosphoryl group whose (C1-C6)alkoxy groups may be the same or different;
a di(C1-C6)alkoxythiophosphoryl group whose (C1-C6)alkoxy groups may be the same or different;
a phenyl group;
a substituted phenyl group having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C5)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups;
a phenyl(C1-C4)alkyl group;
a substituted phenyl(C1-C4)alkyl group having on the ring one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups;
a heterocyclic group;
or a substituted heterocyclic group having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups), and r is an integer of 1 to
4),provided that R1 and R2 are not hydrogen atoms at the same time, R1 and R2 together with the N to which they are attached may form a 4 to 7 membered ring by combining to each other, in which the ring may contain the same or different 1 to 3 hetero atoms selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom, Het is a heterocyclic group represented by any of the following formulas Q1 to Q4;
(wherein X, which may be the same or different, are halogen atoms;
cyano groups;
nitro groups;
(C3-C6)cycloalkyl groups;
halo(C3-C6)cycloalkyl groups;
tri(C1-C6)alkylsilyl groups whose (C1-C6)alkyl groups may be the same or different;
phenyl groups;
substituted phenyl groups having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups;
heterocyclic groups;
substituted heterocyclic groups having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups;
or —
A3—
R8
wherein A3 is —
O—
, —
S—
, —
SO—
, —
SO2—
, —
N(R6)—
(wherein R6 is as defined above), —
C(═
O)—
, —
C(═
NOR7)—
(wherein R7 is as defined above), a (C1-C6)alkylene group, a halo(C1-C6)alkylene group, a (C2-C6)alkenylene group, a halo(C2-C6)alkenylene group, a (C2-C6)alkynylene group or a halo(C3-C6)alkynylene group, and R8 is as follows;
(1) when A3 is —
O—
, —
S—
, —
SO—
, —
SO2—
or —
N(R6)—
(wherein R6 is as defined above), then R8 is a halo(C3-C6)cycloalkyl group;
a halo(C3-C6)cycloalkenyl group;
a phenyl group;
a substituted phenyl group having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups;
a heterocyclic group;
a substituted heterocyclic group having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups;
or —
A4—
R9 (wherein A4 is a (C1-C6)alkylene group, a halo(C1-C6)alkylene group, a (C3-C6)alkenylene group, a halo(C3-C6)alkenylene group, a (C3-C6)alkynylene group or a halo(C3-C6)alkynylene group, and R9 is a hydrogen atom;
a halogen atom;
a (C3-C6)cycloalkyl group;
a halo(C3-C6)cycloalkyl group;
a (C1-C6)alkoxycarbonyl group;
a phenyl group;
a substituted phenyl group having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups;
or —
A5—
R10 (wherein A5 is —
O—
, —
S—
, —
SO—
, —
SO2—
or —
C(═
O), and R10 is a (C1-C6)alkyl group;
a halo(C1-C6)alkyl group;
a (C3-C6)alkenyl group;
a halo(C3-C6)alkenyl group;
a (C3-C6)cycloalkyl group;
a halo(C3-C6)cycloalkyl group;
a phenyl group;
a substituted phenyl group having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups;
a heterocyclic group;
or a substituted heterocyclic group having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups)),(2) when A3 is —
C(═
O)—
or —
C(═
NOR7)—
(wherein R7 is as defined above), then R8 is a hydrogen atom;
a (C1-C6)alkyl group;
a halo(C1-C6)alkyl group;
a (C2C6)alkenyl group;
a halo(C2C6)alkenyl group;
a (C3-C6)cycloalkyl group;
a halo(C3-C6)cycloalkyl group;
a (C1-C6)alkoxy group;
a (C1-C6)alkylthio group;
a mono(C1-C6)alkylamino group;
a di(C1-C6)alkylamino group whose (C1-C6)alkyl groups may be the same or different;
a phenyl group;
a substituted phenyl group having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups;
a phenylamino group;
a substituted phenylamino group having on the ring one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups;
a heterocyclic group;
or a substituted heterocyclic group having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups, and(3) when A3 is a (C1-C6)alkylene group, a halo(C1-C6)alkylene group, a (C2-C6)alkenylene group, a halo(C2-C6)alkenylene group, a (C2-C6)alkynylene group or a halo(C3-C6)alkynylene group, then R8 is a hydrogen atom;
a halogen atom;
a (C3-C6)cycloalkyl group;
a halo(C3-C6)cycloalkyl group;
a (C1-C6)alkoxycarbonyl group;
a tri(C1-C6)alkylsilyl group whose (C1-C6)alkyl groups may be the same or different;
a phenyl group;
a substituted phenyl group having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups;
a heterocyclic group;
a substituted heterocyclic group having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups;
or —
A—
R11 (wherein A6 is —
O—
, —
S—
, —
SO—
or —
SO2—
, and R11 is a (C3-C6)cycloalkyl group;
a halo(C3-C6)cycloalkyl group;
a phenyl group;
a substituted phenyl group having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups;
a heterocyclic group;
a substituted heterocyclic group having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups;
or —
A7—
R12 (wherein A7 is a (C1-C6)alkylene group, a halo(C1-C6)alkylene group, a (C2-C6)alkenylene group, a halo(C2-C6)alkenylene group, a (C2-C6)alkynylene group or a halo(C3-C6)alkynylene group, and R12 is a hydrogen atom;
a halogen atom;
a (C3-C6)cycloalkyl group;
a halo(C3-C6)cycloalkyl group;
a (C1-C6)alkoxy group;
a halo(C1-C6)alkoxy group;
a (C1-C6)alkylthio group;
a halo(C1-C6)alkylthio group;
a (C1-C6)alkylsulfinyl group;
a halo(C1-C6)alkylsulfinyl group;
a (C1-C6)alkylsulfonyl group;
a halo(C1-C6)alkylsulfonyl group;
a phenyl group;
a substituted phenyl group having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups;
a phenoxy group;
a substituted phenoxy group having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C8)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C5)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups;
a phenylthio group;
a substituted phenylthio group having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups;
a heterocyclic group;
or a substituted heterocyclic group having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups))
, and n is an integer of 0 to 3,X may form a condensed ring selected from the group consisting of indole ring, benzo[b]furan ring, benzo[b]thiophene ring, quinoline ring, isoquinoline ring, naphthyridine ring, quinoxaline ring and cinnoline ring, by combining together with the adjacent atoms in the heterocyclic ring, and said condensed ring may have one or more substituents, which may be the same or different, and are selected from halogen atoms;
(C1-C6)alkyl groups;
halo(C1-C6)alkyl groups;
(C1-C6)alkoxy groups;
halo(C1-C6)alkoxy groups;
(C1-C6)alkylthio groups;
halo(C1-C6)alkylthio groups;
(C1-C6)alkylsulfinyl groups;
halo(C1-C6)alkylsulfinyl groups;
(C1-C6)alkylsulfonyl groups;
halo(C1-C6)alkylsulfonyl groups;
phenyl group;
substituted phenyl groups having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups;
heterocyclic groups; and
substituted heterocyclic groups having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups,W is O, S or N—
R13 (wherein R13 is a (C1-C6)alkyl group;
a halo(C1-C6)alkyl group;
a (C3-C6)alkenyl group;
a halo(C3-C6)alkenyl group;
a (C3-C6)alkynyl group;
a halo(C3-C6)alkynyl group;
a (C1-C6)alkoxy group;
a phenyl group;
a substituted phenyl group having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups;
a phenyl(C1-C6)alkyl group;
or a substituted phenyl(C1-C6)alkyl group having on the ring one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups), and p and q, which may be the same or different, are integers of 0 to
1),B1, B2, B3 and B4, which may be the same or different, are carbon atoms, Y, which may be the same or different, are halogen atoms;
cyano groups;
nitro groups;
halo(C3-C6)cycloalkyl groups;
phenyl groups;
substituted phenyl groups having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups;
heterocyclic groups;
substituted heterocyclic groups having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups;
or —
A3—
R3 (wherein A3 and R8 are as defined above), and m is an integer of 1 to 5,Y may form a condensed ring by combining together with the adjacent carbon atoms in the aromatic ring, and said condensed ring may have one or more substituents, which may be the same or different, and are selected from halogen atoms;
(C1-C6)alkyl groups;
halo(C1-C6)alkyl groups;
(C1-C6)alkoxy groups;
halo(C1-C6)alkoxy groups;
(C1-C6)alkylthio groups;
halo(C1-C6)alkylthio groups;
(C1-C6)alkylsulfinyl groups;
halo(C1-C6)alkylsulfinyl groups;
(C1-C6)alkylsulfonyl groups;
halo(C1-C6)alkylsulfonyl groups;
phenyl group;
substituted phenyl groups having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups;
heterocyclic groups; and
substituted heterocyclic groups having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups, and each of Z1 and Z2 is an oxygen atom or a sulfur atom,provided that;
(1) when Het is Q2, and B1, B2, B3 and B4 are carbon atoms at the same time, then Ym is other than 3-chloro-2-methyl group, 3-chloro-2,6-diethyl group, 5chloro-2-methyl group, 2,6-diethyl group, 4-chloro-2-fluoro group and 2-ethyl-6-methyl group, and (2) when Het is Q4 and B1, B2, B3 and B4 are carbon atoms at the same time, then Ym is other than 2,5-dichloro group, 2,4-difluoro group, 2,6-difluoro group, 3-chloro-2-methyl group, 5-chloro-2-methyl group, 5-fluoro-2-methyl group, 2,6-dimethyl group, 2,6-diethyl group, 2-ethyl-6-methyl group, 2-methoxy-5-nitro group, 2-methoxy-5methyl group, 2,6-diethoxy group, 3-bromo-2-methyl group, 3-fluoro-2-methyl group, 3-iodo-2-methyl group, 3-cyano-2-methyl group, 3-difluoromethoxy-2-methyl group, 5-chloro-2-ethyl group, 2,5-dimethyl group, 2,3-dichloro group, 3-chloro2,6-diethyl group, 4-trifluoromethyl group, 3-methoxycarbonyl-2-methyl group, 3-trifluoromethyl-2-methyl group, 3,5-dichloro-2,6diethyl group, 3,4-dichloro group, 3-(methoxycarbonylmethyloxy)-2-methyl group, 2-methyl-3-nitro group and 4-trifluoromethoxy group. - View Dependent Claims (2, 3, 4, 5, 6, 7)
(1) when A3 is —
O—
, —
S—
, —
SO—
or —
SO2—
, then R8 is a phenyl group;
a substituted phenyl group having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups;
a pyridyl group;
a substituted pyridyl group having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups;
or —
A4—
R9 (wherein A4 is a (C1-C6)alkylene group, a halo(C1-C6)alkylene group, a (C3-C6)alkenylene group, a halo(C3-C6)alkenylene group, a (C3-C6)alkynylene group or a halo(C3-C6)alkynylene group, and R9 is a hydrogen atom, a halogen atom or —
A5—
R10 (wherein A5 is —
O—
, —
S—
, —
SO—
or —
SO2—
, and R10 is a (C1-C6)alkyl group, a halo(C1-C6)alkyl group, a (C3-C6)alkenyl group, a halo(C3-C6)alkenyl group, a (C3-C6)cycloalkyl group or a halo(C3-C6)cycloalkyl group)), and(2) when A3 is a (C1-C6)alkylene group, a halo(C1-C6)alkylene group, a (C2-C6)alkenylene group, a halo(C2-C6)alkenylene group, a (C2-C6)alkynylene group or a halo(C3-C6)alkynylene group, then R8 is a hydrogen atom;
a halogen atom;
a (C3-C6)cycloalkyl group;
a halo(C3-C6)cycloalkyl group;
a tri(C1-C6)alkylsilyl group whose (C1-C6)alkyl groups may be the same or different;
a phenyl group;
a substituted phenyl group having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups;
a pyridyl group;
a substituted pyridyl group having one or more substituents which may be the same or different and are selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups and halo(C1-C6)alkylsulfonyl groups;
or —
A6—
R11 (wherein A6 is —
O—
, —
S—
, —
SO—
or —
SO2—
, and R11 is —
A7—
R12 (wherein A7 is a (C1-C6)alkylene group, a halo(C1-C6)alkylene group, a (C2-C6)alkenylene group, a halo(C2-C6)alkenylene group, a (C2-C6)alkynylene group or a halo(C3-C6)alkynylene group, and R12 is a hydrogen atom, a halogen atom, a (C1-C6)alkoxy group, a halo(C1-C6)alkoxy group, a (C1-C6)alkylthio group, a halo(C1-C6)alkylthio group, a (C1-C6)alkylsulfinyl group, a halo(C1-C6)alkylsulfinyl group, a (C1-C6)alkylsulfonyl group or a halo(C1-C6)alkylsulfonyl group))], both B1 and B4 are carbon atoms, B2 and B3, which may be the same or different, are carbon atoms or nitrogen atoms, and each of Z1 and Z2 is an oxygen atom.
-
-
3. A heterocyclic dicarboxylic acid diamide derivative according to claim 2, wherein X, which may be the same or different, are halogen atoms, nitro groups, halo(C1-C6)alkyl groups, halo(C1-C6)alkoxy groups or halo(C1-C6)alkylthio groups, and n is an integer of 0 to 3.
-
4. A heterocyclic dicarboxylic acid diamide derivative according to claim 3, wherein Y, which may be the same or different, are halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)-alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, halo(C1-C6)alkoxyhalo(C1-C6)alkoxy groups, halo(C1-C6)-alkoxyhalo(C1-C6)alkylthio groups, halo(C1-C6)alkylsulfinyl groups or halo(C1-C6)alkylsulfonyl groups, and m is an integer of 1 to 5.
-
5. A heterocyclic dicarboxylic acid diamide derivative according to claim 4, wherein R1 is a (C1-C6)alkyl group, a (C1-C6)alkoxy(C1-C8)alkyl group, a (C1-C6)alkylthio(C1-C8)-alkyl group, a (C1-C6)alkylsulfinyl(C1-C8)alkyl group or a (C1-C6)alkylsulfonyl(C1-C8)alkyl group, and R2 and R3, which may be the same or different, are hydrogen atoms or methyl groups.
-
6. An agricultural and horticultural insecticide characterized by containing a heterocyclic dicarboxylic acid diamide derivative according to claim 1 as an active ingredient.
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7. A method for applying an agricultural and horticultural insecticide, characterized by treating a crop to be protected or soil with an effective amount of an agricultural and horticultural insecticide according to claim 6 in order to protect useful crops against insect pests.
Specification
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Current AssigneeNihon Nohyaku Co., Ltd. (Adeka Corporation)
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Original AssigneeNihon Nohyaku Co., Ltd. (Adeka Corporation)
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InventorsMorimoto, Masayuki, Takaishi, Hideo, Furuya, Takashi, Sakata, Kazuyuki, Tohnishi, Masanori, Seo, Akira, Katsuhira, Takeshi, Gotoh, Makoto
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Primary Examiner(s)Berch, Mark L.
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Assistant Examiner(s)Habte, Kahsay
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Application NumberUS10/018,463Time in Patent Office790 DaysField of Search514/307, 514/309, 514/311, 514/312, 514/355, 514/354, 546/316, 546/323, 546/141, 546/146, 546/156, 546/169, 546/313US Class Current514/307CPC Class CodesA01N 43/08 with oxygen as the ring het...A01N 43/10 with sulfur as the ring het...A01N 43/40 six-membered ringsA01N 43/50 1,3-Diazoles; Hydrogenated ...A01N 43/54 1,3-Diazines; Hydrogenated ...A01N 43/56 1,2-Diazoles; Hydrogenated ...A01N 43/58 1,2-Diazines; Hydrogenated ...A01N 43/60 1,4-Diazines; Hydrogenated ...A01N 43/80 five-membered rings with on...C07D 207/34 with hetero atoms or with c...C07D 213/82 in position 3C07D 213/89 with hetero atoms directly ...C07D 231/14 with hetero atoms or with c...C07D 231/16 Halogen atoms or nitro radi...C07D 233/90 Carbon atoms having three b...C07D 237/24 Carbon atoms having three b...C07D 239/28 with hetero atoms or with c...C07D 239/30 Halogen atoms or nitro radi...C07D 239/38 One sulfur atomC07D 241/24 Carbon atoms having three b...View All
