US 7,696,129 B2 · Substituted aromatic amide derivative, intermediate thereof, agrohorticultural insecticide containing thereof and method for the use thereof

Abstract

The present invention provides a substituted anilide derivative of formula (I): {wherein Z is a group of formula (II) or (III) (in these formulas, A is C1-C6 alkylene, C2-C6 alkenylene, etc., R1 is H, halogen, —C(R5)═NOR6, (substituted) phenyl, (substituted) heterocyclic ring, -A1-R7, etc.; R2 is H, C1-C4 alkyl, etc.), R3 is H, C1-C4 alkyl, etc.; R4 is H, F, fluoro C1-C6 alkyl; Rf is F, fluoro C1-C6 alkyl; 1 is 0 to 2; Y is halogen, (substituted) phenyl, (substituted) phenoxy, etc.; and m is 0 to 3}, an intermediate thereof, an agrohorticultural agent, and a method for the use thereof. The compound of the present invention exhibits, at a low dosage, high uptake and translocation from the root and an excellent insecticidal effect especially when applied to soil.

A compound represented by formula (I):

{wherein Z represents formula (II):
(wherein A, R1 and R2 are as defined below), or formula (III):
(wherein A represents a C1-C6 alkylene group;
a substituted C1-C6 alkylene group having at least one, the same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, C1-C6 alkylthio C1-C6 alkyl group, C1-C6 alkoxycarbonyl group and phenyl group;
a C2-C6 alkenylene group, a substituted C2-C6 alkenylene group having at least one, the same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, C1-C6 alkylthio C1-C6 alkyl group, C1-C6 alkoxycarbonyl group and phenyl group;
a C2-C6 alkynylene group;
or a substituted C3-C6 alkynylene group having at least one, the same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, C1-C6 alkylthio C1-C6 alkyl group, C1-C6 alkoxycarbonyl group and phenyl group;
and an arbitrarily selected saturated carbon atom in the C1-C6 alkylene group, substituted C1-C6 alkylene group, C3-C6 alkenylene group, substituted C3-C6 alkenylene group, C3-C6 alkynylene group or substituted C3-C6 alkynylene group may be substituted with a C2-C5 alkylene group to form a C3-C6 cycloalkane ring, and arbitrarily selected two carbon atoms in the C2-C6 alkylene group, substituted C2-C6 alkylene group, C3-C6 alkenylene group or substituted C3-C6 alkenylene group may be taken conjointly with an alkylene group or an alkenylene group to form a C3-C6 cycloalkane ring or a C3-C6 cycloalkene ring;
R1 represents a hydrogen atom;
a halogen atom;
a cyano group;
a nitro group;
a C3-C6 cycloalkyl group;
a C1-C6 alkoxycarbonyl group;
a mono C1-C6 alkylaminocarbonyl group;
a di C1-C6 alkylaminocarbonyl group which the C1-C6 alkyl groups may be the same or different;
a mono C1-C6 alkylaminosulfonyl group;
a di C1-C6 alkylaminosulfonyl group which the C1-C6 alkyl groups may be the same or different, a di C1-C6 alkoxyphosphoryl group which the C1-C6 alkyl groups may be the same or different, a di C1-C6 alkoxythiophosphoryl group which the C1-C6 alkyl groups may be the same or different;
—C(R5)═NOR6 (in this formula, R5 represents a hydrogen atom or a C1-C6 alkyl group;
and R6 represents a hydrogen atom;
a C1-C6 alkyl group;
a C3-C6 alkenyl group;
a C3-C6 alkynyl group;
a C3-C6 cycloalkyl group;
a phenyl C1-C4 alkyl group;
or a substituted phenyl C1-C4 alkyl group having, on the ring thereof, at least one, the same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group and C1-C6 alkylthio group);
a phenyl group;
a substituted phenyl group having at least one, the same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group;
a heterocyclic group;
a substituted heterocyclic group having at least one, the same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group;
or -A1-R7 (in this formula, A1 represents —O—, —S—, —SO—, —SO2— or —N(R6)— (in this formula, R6 is as defined above);
and R7 represents 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 phenyl group;
a substituted phenyl group having at least one, the same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group and C1-C6 alkoxycarbonyl group;
a phenyl C1-C4 alkyl group;
a substituted phenyl C1-C4 alkyl group having, on the ring thereof, at least one, the same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group and C1-C6 alkoxycarbonyl group;
a heterocyclic group;
a substituted heterocyclic group having, on the ring thereof, at least one, the same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group and C1-C6 alkoxycarbonyl group;
a C1-C6 alkylcarbonyl group;
a halo C1-C6 alkylcarbonyl group;
a C1-C6 alokoxycarbonyl group;
a mono C1-C6 alkylaminocarbonyl group;
a di C1-C6 alkylaminocarbonyl group which the C1-C6 alkyl groups may be the same or different;
a C1-C6 alkylsulfonyl group;
a halo C1-C6 alkylsulfonyl group;
a mono C1-C6 alkylaminosulfonyl group;
a di C1-C6 alkylaminosulfonyl group which the C1-C6 alkyl groups may be the same or different;
a di C1-C6 alkoxyphosphoryl group which the C1-C6 alkyl groups may be the same or different;
or a di C1-C6 alkoxythiophosphoryl group which the C1-C6 alkyl groups may be the same or different);
R2 represents a hydrogen atom;
a C1-C4 alkyl group;
a C1-C4 alkoxy C1-C4 alkyl group;
or a C1-C4 alkylthio C1-C4 alkyl group;
and R2 may be taken conjointly together with A or R1 to form one to three, the same or different, 5- to 7-membered rings which may be intercepted by oxygen atom, sulfur atom or nitrogen atom);
R3 represents a hydrogen atom;
a C1-C4 alkyl group;
a C1-C4 alkoxy C1-C4 alkyl group;
or a C1-C4 alkylthio C1-C4 alkyl group;
R4 represents a fluoro C1-C6 alkyl group;
and Rf represents a fluoro C1-C6 alkyl group;
Q1 to Q6, Q8 and Q9 represent a carbon atom;
X which may be the same or different represent a halogen atom;
a nitro group;
a cyano group;
a C1-C6 alkyl group;
a halo C1-C6 alkyl group;
a C2-C6 alkenyl group;
a halo C2-C6 alkenyl group;
a C2-C6 alkynyl group;
a halo C2-C6 alkynyl 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;
or a halo C1-C6 alkylsulfonyl group;
and two groups of X residing in adjacent positions on the aromatic ring may be taken conjointly to form a fused ring, and said fused ring may have at least one, the same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group;
and I represents an integer of 0 to 2;
Y which may be the same or different represents a halogen atom;
a C1-C6 alkyl group;
a halo C1-C6 alkyl group;
a cyclo C3-C6 alkyl group;
a C1-C6 alkoxy group;
a halo C1-C6 alkoxy group;
a mono C1-C6 alkylamino group;
a di C1-C6 alkylamino group which the C1-C6 alkyl groups may be the same or different;
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 at least one, the same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group;
a phenyl C1-C4 alkyl group;
a substituted phenyl C1-C4 alkyl group having, on the ring thereof, at least one, the same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group;
a phenoxy group;
a substituted phenoxy group having at least one, the same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group;
a phenylthio group;
a substituted phenylthio group having at least one, the same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group;
a heterocyclic group;
or a substituted heterocyclic group having at least one, the same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group;
and two groups of Y residing in adjacent positions on the aromatic ring may be taken conjointly to form a fused ring, and said fused ring may have at least one, the same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group;
and Y may be taken conjointly with R3 to form a 5- to 7-membered ring which may be intercepted by one or two, the same or different oxygen atoms, sulfur atoms or nitrogen atoms;
and
m represents an integer of 0 to 3}.

112 more elements

Substituted aromatic amide derivative, intermediate thereof, agrohorticultural insecticide containing thereof and method for the use thereof

Life of this patent

Substituted aromatic amide derivative, intermediate thereof, agrohorticultural insecticide containing thereof and method for the use thereof

Life of this patent

Abstract

Claims13