PHTHALIC ACID DIAMIDE DERIVATIVES FLUORINE-CONTAINING ANILINE COMPOUNDS AS STARTING MATERIAL, AGRICULTURAL AND HORTICULTURAL INSECTICIDES, AND A METHOD FOR APPLICATION OF THE INSECTICIDES
First Claim
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1. A phthalic acid diamide derivative represented by the general formula (I),
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Abstract
The present invention provides a phthalic acid diamide derivative represented by the general formula (I)
(wherein R1, R2 and R3 are each H, C3-C6 cycloalkyl group, group of the formula —A1—Ql or the like; X may be the same or different and are each halogen atom, nitro group, phenyl group, group of the formula —A2—R7 or the like; n is 1 to 4; Y may be same or different and are each halogen atom, cyano group, phenyl group, group of the formula —A2—R7 or the like; m is 1 to 5; Z1 and Z2 are each O or S), fluorine-containing aniline compound represented by the general formula (ST-I) as starting material for said phthalic acid diamide derivative
(wherein Ra is halogen atom, C1-C6 alkyl group or the like and Rb, Rc and Rd is H or C2-C6 perfluoroalkyl group), and an agricultural and horticultural insecticide containing said phthaldiamide derivative, as well as to provide a method for use of said insecticide. The agricultural and horticultural insecticides of the present invention show excellent activities for controlling injurious insects.
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Citations
15 Claims
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1. A phthalic acid diamide derivative represented by the general formula (I),
- View Dependent Claims (2, 3, 4, 5)
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2. The phthalic acid diamide derivative according to
claim 1 , wherein R1, R2 and R3 may be the same or different, and are each a hydrogen atom, a C3-C6 cycloalkyl group, a halo-C3-C6 cycloalkyl group, or a group of the formula —- A1—
Ql (wherein A1 is a C1-C6 alkylene group, a C3-C6 alkenylene group or a C3-C6 alkynylene group; and
Q is a hydrogen atom, a halogen atom, a cyano group, a nitro group, a halo-C1-C6 alkyl group, a C3-C6 cycloalkyl group, a halo-C3-C6 cycloalkyl group, a C1-C6 alkoxycarbonyl group, a di-C1-C6 alkoxyphosphoryl group which may be the same or different, a di-C1-C6 alkoxythiophosphoryl group which may be the same or different, a diphenylphosphino group, a diphenylphosphono group, a phenyl group, a substituted phenyl group having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group, a heterocyclic group (which means pyridyl group, pyridine-N-oxide group, pyrimidinyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydropyranyl group, tetrahydrothiopyranyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, imidazolyl group, triazolyl group or pyrazolyl group), a substituted heterocyclic group (wherein the heterocyclic group is the same as defined above) having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group, or a group of the formula —
Z3—
R5 (wherein Z3 is —
O—
, —
S—
, —
SO—
SO SO2—
or a group of the formula —
N(R6)—
(wherein R6 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 at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group, a phenyl C1-C4 alkoxycarbonyl group, or a substituted phenyl C1-C4 alkoxycarbonyl group having at least one substituent, in the phenyl ring, which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group); 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 alkylcarbonyl group, a halo C1-C6 alkylcarbonyl group, a C1-C6 alkoxycarbonyl group, a phenyl group, a substituted phenyl group having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group, a phenyl C1-C4 alkyl group, a substituted phenyl C1-C4 alkyl group having at least one substituent, in the phenyl ring, which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group, a heterocyclic group (which is the same as defined above), or a substituted heterocyclic group (wherein the heterocyclic group is the same as defined above) having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group); and
t is an integer of 1 to
4);
R1 and R2 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;
X may be the same or different, and is a hydrogen atom, a halogen atom, a cyano group, a nitro group, a C3-C6 cycloalkyl group, a halo-C3-C6 cycloalkyl group, a phenyl group, a substituted phenyl group having at least one substituents which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group, a heterocyclic group (which is the same as defined the above), a substituted heterocyclic group (wherein the heterocyclic group is the same as defined above) having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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, and a halo-C1-C6 alkylsulfonyl group, or a group of the formula —
A2—
R7 (wherein A2 is —
O—
, —
S—
, —
SO—
, —
SO2—
, —
C(═
O)—
, —
C(═
NOR8)—
(wherein R8 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 C3-C6 cycloalkyl group, a phenyl-C1-C4 alkyl group, or a substituted phenyl-C1-C4 alkyl group having at least one substituent, in the phenyl ring, which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group), 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;
(1) when A2 is —
O—
, —
S—
, —
SO—
or —
SO2—
, then R7 is a halo-C3-C6 cycloalkyl group, a halo-C3-C6 cycloalkenyl group, a phenyl group, a substituted phenyl group having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group, a heterocyclic group (which is the same as defined above), a substituted heterocyclic group (wherein the heterocyclic group is the same as defined above) having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group, or a group of the formula —
A3—
R9 (wherein A3 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;
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 at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group, or a group of the formula —
A4—
R10 (wherein A4 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 at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group, a heterocyclic group (which is the same as defined the above), or a substituted heterocyclic group (wherein the heterocyclic group is the same as defined above) having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group));
(2) when A2 is —
C(═
O)—
or a group of the formula —
C(═
NOR8)—
(wherein R8 is the same as defined the above), then R7 is a C1-C6 alkyl group, a halo C1-C6 alkyl group, a C2-C6 alkenyl group, a halo-C2-C6 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 which may be the same or different, a phenyl group, a substituted phenyl group having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group, a phenylamino group, a substituted phenylamino group having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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, and a halo-C1-C6 alkylsulfonyl group, a heterocyclic group (which is the same as defined the above), or a substituted heterocyclic group (wherein the heterocyclic group is the same as defined the above) having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group,(3) when A2 is a C1-C6 alkylene group, a halo-C1-C6 alkylene group, C2-C6 alkenylene group, a halo-C2-C6 alkenylene group, a C2-C6 alkynylene group or a halo-C3-C6 alkynylene group, then R7 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 at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group, a heterocyclic group (which is the same as defined the above), a substituted heterocyclic group (wherein the heterocyclic group is the same as defined above) having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group, or a group of the formula —
A5—
R12 (wherein A5 is —
O—
, —
S—
, —
SO—
or —
SO2—
; and
R12 is a C3-C6 cycloalkyl group, a halo-C3-C6 cycloalkyl group, a phenyl group, a substituted phenyl group having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group, a heterocyclic group (which is the same as defined the above), a substituted heterocyclic group (wherein the heterocyclic group is the same as defined above) having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group, or a group of the formula —
A6—
R14 (wherein A6 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
R14 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 at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group, a phenoxy group, a substituted phenoxy group having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group, a phenylthio group, a substituted phenylthio group having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6-alkylsulfonyl group, a heterocyclic group (which is the same as defined the above), or a substituted heterocyclic group (wherein the heterocyclic ring is the same as defined above) having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group)));
n is an integer of 1 to 4;
further, X may form a condensed ring (which means naphthalene, tetrahydronaphthalene, indene, indane, quinoline, quinazoline, chroman, isochroman, indole, indoline, benzodioxane, benzodioxole, benzofuran, dihydrobenzofuran, benzothiophene, dihydrobenzothiophene, benzoxazole, benzothiazole, benzimidazole or indazole), by combining together with the adjacent carbon atoms in the phenyl ring, said condensed ring may have at least one substituent, which may be the same or different, and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group, a heterocyclic group (which is the same as defined above), and a substituted heterocyclic group (wherein the heterocyclic group is the same as defined above) having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group;
Y is the same or different, and is a hydrogen atom, a halogen atom, a cyano group, a nitro group, a halo-C3-C6 cycloalkyl group, a phenyl group, a substituted phenyl group having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group, a heterocyclic group (which is the same as defined above), a substituted heterocyclic group (wherein the heterocyclic group is the same as defined above) having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group, or a group of the formula —
A2—
R7 (wherein A2 and R7 are the same as defined above);
m is an integer of 1 to 5;
further, Y may form a condensed ring (the same as defined above), by combining together with the adjacent carbon atoms in the phenyl ring, said condensed ring may have at least one substituent, which may be the same or different, and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group, a heterocyclic group (which is the same as defined the above), and a substituted heterocyclic group (wherein said heterocyclic group is the same as defined the above) having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group; and
Z1 and Z2 are each represents an oxygen atom or a sulfur atom.
- A1—
-
3. The phthalic acid diamide derivative according to
claim 2 , represented by the general formula (I-1), -
4. The phthalic acid diamide derivative according to
claim 2 , represented by the general formula (I-2), -
5. The phthalic acid diamide derivative according to
claim 4 , represented by the general formula (I-3),
-
2. The phthalic acid diamide derivative according to
-
6. An agricultural and horticultural insecticides, which is characterized by containing, as the effective ingredient, a phthalic acid diamide derivative represented by the general formula (I),
- View Dependent Claims (7, 8, 9, 10, 11)
-
7. The agricultural and horticultural insecticides according to
claim 6 ,wherein R1, R2 and R3 may be the same or different, and are each a hydrogen atom, a C3-C6 cycloalkyl group, a halo-C3-C6 cycloalkyl group, or a group of the formula — - A1—
Ql (wherein A1 is a C1-C8 alkylene group, a C3-C6 alkenylene group or a C3-C6 alkynylene group; and
Q is a hydrogen atom, a halogen atom, a cyano group, a nitro group, a halo-C1-C6 alkyl group, a C3-C6 cycloalkyl group, a halo-C3-C6 cycloalkyl group, a C1-C6 alkoxycarbonyl group, a di-C1-C6 alkoxyphosphoryl group which may be the same or different, a di-C1-C6 alkoxythiophosphoryl group which may be the same or different, a diphenylphosphino group, a diphenylphosphono group, a phenyl group, a substituted phenyl group having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group, a heterocyclic group (which means pyridyl group, pyridine-N-oxide group, pyrimidinyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydropyranyl group, tetrahydrothiopyranyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, imidazolyl group, triazolyl group or pyrazolyl group), a substituted heterocyclic group (wherein the heterocyclic group is the same as defined above) having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group, or a group of the formula —
Z3—
R5 (wherein Z3 is —
O—
, —
S—
, —
SO—
, —
SO2—
or a group of the formula —
N(R6)—
(wherein R6 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 at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group, a phenyl C1-C4 alkoxycarbonyl group, or a substituted phenyl C1-C4 alkoxycarbonyl group having at least one substituent, in the phenyl ring, which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group,); 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 alkylcarbonyl group, a halo C1-C6 alkylcarbonyl group, a C1-C6 alkoxycarbonyl group, a phenyl group, a substituted phenyl group having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group, a phenyl C1-C4 alkyl group, a substituted phenyl C1-C4 alkyl group having at least one substituent, in the phenyl ring, which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group, a heterocyclic group (which is the same as defined above), or a substituted heterocyclic group (wherein the heterocyclic group is the same as defined above) having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group); and
e is an integer of 1 to
4);
R1 and R2 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;
X may be the same or different, and is a hydrogen atom, a halogen atom, a cyano group, a nitro group, a C3-C6 cycloalkyl group, a halo-C3-C6 cycloalkyl group, a phenyl group, a substituted phenyl group having at least one substituents which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group, a heterocyclic group (which is the same as defined the above), a substituted heterocyclic group (wherein the heterocyclic group is the same as defined above) having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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, and a halo-C1-C6 alkylsulfonyl group, or a group of the formula —
A2—
R7 (wherein A2 is —
O—
, —
S—
, —
SO—
SO SO2—
—
C(═
O)—
, —
C(═
NOR8)—
(wherein R8 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 C3-C6 cycloalkyl group, a phenyl-C1-C4 alkyl group, or a substituted phenyl-C1-C4 alkyl group having at least one substituent, in the phenyl ring, which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group), 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;
(1) when A2 is —
O—
, —
S—
, —
SO—
or —
SO2—
, then R7 is a halo-C3-C6 cycloalkyl group, a halo-C3-C6 cycloalkenyl group, a phenyl group, a substituted phenyl group having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group, a heterocyclic group (which is the same as defined above), a substituted heterocyclic group (wherein the heterocyclic group is the same as defined above) having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group, or a group of the formula —
A3—
R9 (wherein A3 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;
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 at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group, or a group of the formula —
A4—
R10 (wherein A4 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 at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group, a heterocyclic group (which is the same as defined the above), or a substituted heterocyclic group (wherein the heterocyclic group is the same as defined above) having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group));
(2) when A2 is —
C(═
O)—
or a group of the formula —
C(═
NOR8)—
(wherein R8 is the same as defined the above), then R7 is a C1-C6 alkyl group, a halo C1-C6 alkyl group, a C2-C6 alkenyl group, a halo-C2-C6 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 which may be the same or different, a phenyl group, a substituted phenyl group having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group, a phenylamino group, a substituted phenylamino group having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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, and a halo-C1-C6 alkylsulfonyl group, a heterocyclic group (which is the same as defined the above), or a substituted heterocyclic group (wherein the heterocyclic group is the same as defined the above) having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group,(3) when A2 is a C1-C6 alkylene group, a halo-C1-C6 alkylene group, C2-C6 alkenylene group, a halo-C2-C6 alkenylene group, a C2-C6 alkynylene group or a halo-C3-C6 alkynylene group, then R7 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 at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group, a heterocyclic group (which is the same as defined the above), a substituted heterocyclic group (wherein the heterocyclic group is the same as defined above) having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group, or a group of the formula —
A5—
R12 (wherein A5 is —
O—
, —
S—
, —
SO—
or —
SO2—
; and
R12 is a C3-C6 cycloalkyl group, a halo-C3-C6 cycloalkyl group, a phenyl group, a substituted phenyl group having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group, a heterocyclic group (which is the same as defined the above), a substituted heterocyclic group (wherein the heterocyclic group is the same as defined above) having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group, or a group of the formula —
A6—
R14 (wherein A6 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
R14 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 at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group, a phenoxy group, a substituted phenoxy group having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group, a phenylthio group, a substituted phenylthio group having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6-alkylsulfonyl group, a heterocyclic group (which is the same as defined the above), or a substituted heterocyclic group (wherein the heterocyclic ring is the same as defined above) having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group)));
n is an integer of 1 to 4;
further, X may form a condensed ring (which means naphthalene, tetrahydronaphthalene, indene, indane, quinoline, quinazoline, chroman, isochroman, indole, indoline, benzodioxane, benzodioxole, benzofuran, dihydrobenzofuran, benzothiophene, dihydrobenzothiophene, benzoxazole, benzothiazole, benzimidazole or indazole), by combining together with the adjacent carbon atoms in the phenyl ring, said condensed ring may have at least one substituent, which may be the same or different, and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group, a heterocyclic group (which is the same as defined above), and a substituted heterocyclic group (wherein the heterocyclic group is the same as defined above) having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group;
Y is the same or different, and is a hydrogen atom, a halogen atom, a cyano group, a nitro group, a halo-C3-C6 cycloalkyl group, a phenyl group, a substituted phenyl group having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group, a heterocyclic group (which is the same as defined above), a substituted heterocyclic group (wherein the heterocyclic group is the same as defined above) having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group, or a group of the formula —
A2—
R7 (wherein A2 and R7 are the same as defined above);
m is an integer of 1 to 5;
further, Y may form a condensed ring (the same as defined above), by combining together with the adjacent carbon atoms in the phenyl ring, said condensed ring may have at least one substituent, which may be the same or different, and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group, a heterocyclic group (which is the same as defined the above), and a substituted heterocyclic group (wherein said heterocyclic group is the same as defined the above) having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a halo-C1-C6 alkyl 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 and a halo-C1-C6 alkylsulfonyl group; and
Z1 and Z2 are each represents an oxygen atom or a sulfur atom.
- A1—
-
8. The agricultural and horticultural insecticides according to
claim 7 , containing as the effective ingredient, a phthalic acid diamide derivative represented by the general formula (I-1), -
9. The agricultural and horticultural insecticides according to
claim 7 , containing as the active ingredient, a phthalic acid diamide derivative represented by the general formula (I-2), -
10. The agricultural and horticultural insecticides according to
claim 9 , containing as the effective ingredient, a phthalic acid diamide derivative represented by the general formula (I-3), -
11. A method for controlling undesirable insect pests for a useful crop, characterized by treating an objective crop with an effective amount of the agricultural and horticultural insecticides according to
claim 6 .
-
7. The agricultural and horticultural insecticides according to
-
12. A fluorine-containing aniline compound represented by the general formula (ST-I):
- View Dependent Claims (13, 14, 15)
-
13. A fluorine-containing aniline compound according to
claim 12 , wherein Ra is a C1-C6 alkyl group. -
14. A fluorine-containing aniline compound according to
claim 12 , wherein Ra is a chlorine atom or a bromine atom. -
15. A fluorine-containing aniline compound according to
claim 12 , wherein Ra is a fluorine atom, each of Rb and Rd is a hydrogen atom, and Rc is a heptafluoropropan-2-yl group.
-
13. A fluorine-containing aniline compound according to
Specification
-
- Resources
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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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InventorsSAKATA, KAZUYUKI, FURUYA, TAKASHI, FUJIOKA, SHINSUKE, SHIMIZU, TOSHIAKI, TOHNISHI, MASANORI, KANNO, HIDEO, SEO, AKIRA, KOHNO, EIJI, NAKAO, HAYAMI, NISHIDA, TATEKI
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Granted Patent
-
Time in Patent OfficeDays
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Field of Search
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US Class Current564/156
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CPC Class CodesC07C 211/52 the carbon skeleton being f...C07C 233/65 having the nitrogen atoms o...C07C 233/66 having the nitrogen atom of...C07C 233/75 with the substituted hydroc...C07C 233/81 having the nitrogen atom of...C07C 233/91 with carbon atoms of the ca...C07C 233/92 with at least one carbon at...C07C 235/64 having the nitrogen atom of...C07C 235/84 with the carbon atom of at ...C07C 237/22 having nitrogen atoms of am...C07C 251/48 with the carbon atom of at ...C07C 255/57 containing cyano groups and...C07C 261/04 Cyanamides unsubstituted cy...C07C 271/20 to carbon atoms of hydrocar...C07C 271/64 Y being a hydrogen or a car...C07D 213/40 Acylated substituent nitrog...C07D 213/70 Sulfur atomsC07D 263/32 with only hydrogen atoms, h...C07D 277/30 Radicals substituted by car...C07D 295/192 from aromatic carboxylic acidsView AllC07D 307/52 : Radicals substituted by nit...C07D 333/20 : by nitrogen atoms nitro, ni...C07F 9/18 : with hydroxyaryl compoundsC07F 9/4021 : Esters of aromatic acids (P...
