JP2000026431A - 6-alkoxycarbonylpyridazin-3-one compound - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a new compound having an excellent weeding activity to weeds such as Panicum crus-galli and useful as a herbicide, comprising a specific pyridazinone derivative. SOLUTION: This compound is expressed by formula I [R1 is a 1-6C alkyl; R2 is H or a 1-3C alkyl; R3 is a 1-3C haloalkyl; Q is (substituted) phenyl], e.g. 2-(4-chlorophenyl)-6-ethoxycarbonyl-5-trifluoromethylpyridazin-3-one. The compound of formula I is obtained by reacting a compound of formula II (Q1 is a group such as formula III or the like; X is H or a halogen; Y is a halogen, nitro or the like; B1 is H, a halogen or the like) with a compound of the formula: (C6H5)3P=C(R2)COOR33 (C33 is a 1-6C alkyl) [e.g. (carbethoxymethylene) triphenylphospholane] usually in a solvent such as toluene preferably at 20-130 deg.C usually for instant to 72 hrs.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a 6-alkoxycarbonylpyridazin-3-one compound and a herbicide containing the compound as an active ingredient.

[0002]

An object of the present invention is to provide a compound having an excellent herbicidal activity.

[0003]

Means for Solving the Problems The present inventors have conducted intensive studies to find a compound having an excellent herbicidal activity. As a result, they have found that a pyridazinone derivative represented by the following general formula 5 has an excellent herbicidal activity. Invented the invention. That is, the present invention provides a compound represented by the general formula:

Embedded image [Wherein, R ¹ represents a C1-C6 alkyl group, R ² represents a hydrogen atom or a C1-C3 alkyl group, and R ³ represents a C1-C6 alkyl group.
Represents a C3 haloalkyl group, and Q represents an optionally substituted phenyl group. And a herbicide containing the compound as an active ingredient.

[0004]

BEST MODE FOR CARRYING OUT THE INVENTION In the compound of the present invention, the optionally substituted phenyl group represented by Q includes, for example,

Embedded image [Wherein, X represents a hydrogen atom or a halogen atom, Y represents a halogen atom, a nitro group, a cyano group or a trifluoromethyl group, Z ¹ represents an oxygen atom, a sulfur atom, an NH group or a CH ₂ group, Z ² represents an oxygen atom or a sulfur atom, n represents 0 or 1, and R ⁴ represents a hydrogen atom or C1
R ⁵ represents a hydrogen atom, C 1 -C 6
Alkyl group, C1-C6 haloalkyl group, (C3-C8
Cycloalkyl) C1-C6 alkyl group, C3-C6 alkenyl group, C3-C6 haloalkenyl group, C3-C6
Alkynyl group, C3-C6 haloalkynyl group, cyano C
1-C6 alkyl group, C1-C4 alkoxy C1-C4
Alkyl group, C1-C3 alkoxy C1-C3 alkoxy C1-C3 alkyl group, carboxy C1-C6 alkyl group, (C1-C6 alkoxy) carbonyl C1-C6
Alkyl group, {(C1-C4 alkoxy) C1-C4 alkoxy} carbonyl C1-C6 alkyl group, (C3-
C8 cycloalkoxy) carbonyl C1-C6 alkyl ^{_{group, -CH 2 CON (R 12)}} R 13 group, -CH ₂ COON
(R ¹²⁾ R ¹³ group, -CH (C1-C4 alkyl) CON
(R ¹²⁾ R ¹³ group, -CH (C1-C4 alkyl) COO
N (R ¹² ) R ¹³ groups (where R ¹² and R ¹³ are the same or different and are a hydrogen atom, a C1-C6 alkyl group, a C3-C
8 cycloalkyl group, C1-C6 haloalkyl group, C3
-C6 alkenyl group, C3-C6 alkynyl group, cyano C1-C6 alkyl group, C1-C4 alkoxy C1-C
4 alkyl groups, C1-C4 alkylthio C1-C4 alkyl groups, carboxy C1-C6 alkyl groups, (C1-C4
6 alkoxy) carbonyl C1-C6 alkyl group, (C
3-C8 cycloalkoxy) carbonyl C1-C6 alkyl group, (C1-C6 alkyl) carbonyloxy C2
-C6 alkyl group, (C1-C6 alkyl) carbonylamino C2-C6 alkyl group, hydroxy C2-C6 alkyl group, optionally substituted benzyl group, optionally substituted phenyl group, or {(C1-C4 alkoxy) ) C1-C4 alkyl} carbonyl C1-C6 or represents alkyl, or a trimethylene between R ¹² and R ^13,
Represents tetramethylene, pentamethylene, ethyleneoxyethylene or ethylenethioethylene. ), C1-C
Represents a 4-alkylthio C1-C4 alkyl group or a hydroxy C1-C6 alkyl group, and R ⁶ is a C1-C6 alkyl group, a C1-C6 haloalkyl group, a cyano group, a formyl group, a carboxyl group, a hydroxy C1-C6 alkyl group, a C1-C6 alkyl group; C6 alkoxy C1-C6 alkyl group, C1
-C4 alkylthio C1-C4 alkyl group, C1-C6
Alkoxy C1-C6 alkoxy C1-C6 alkyl group, (C1-C6 alkyl) carbonyloxy C1-C
6 represents an alkyl group, (C1-C6 haloalkyl) carbonyloxy C1-C6 alkyl group or (C1-C6 alkoxy) carbonyl group, and R ⁷ represents a hydrogen atom or C1
R ⁸ represents a C1-C6 alkyl group, a C1-C6 haloalkyl group, a hydroxy C1-C6
Alkyl group, C1-C4 alkoxy C1-C4 alkyl group, C1-C3 alkoxy C1-C3 alkoxy C1-
A C3 alkyl group, a (C1-C6 alkyl) carbonyloxy C1-C6 alkyl group, a (C1-C6 haloalkyl) carbonyl C1-C6 alkyl group, a carboxy group,
Carboxy C1-C6 alkyl group, (C1-C8 alkoxy) carbonyl group, (C1-C6 haloalkoxy) carbonyl group, (C3-C10 cycloalkoxy) carbonyl group, (C3-C8 alkenyloxy) carbonyl group, (C3-C8 Alkynyloxy) carbonyl group,
(C1-C6 alkyl) aminocarbonyl group, di (C1
—C6 alkyl) aminocarbonyl group, (C1-C6 alkyl) aminocarbonyloxy C1-C6 alkyl group or di (C1-C6 alkyl) aminocarbonyloxy C1-C6 alkyl group,

B is a hydrogen atom, a halogen atom, a nitro group,
Cyano group, chlorosulfonyl group, OR ^TenGroup, SR^TenGroup,
SO_TwoOR^{twenty one}Group, N (R¹²) R¹³Group, SO_TwoN (R¹²) R
¹³Group, NR¹²(COR⁹) Group, NR¹²(SO_TwoR²⁸) Group,
N (SO_TwoR²⁸) (SO_TwoR²⁹) Group, N (SO_TwoR²⁸)
(COR⁹) Group, NHCOOR¹¹Group, CONR¹²R
¹³Group, CSNR¹²R¹³Group, COR³⁰Group, CR^{twenty three}= CR^{twenty four}
COR³⁰Group, CR^{twenty three}= CR^{twenty four}CON (R¹²) R¹³Group, C
H_TwoCHWCON (R¹²) R¹³Group, CR³⁰= NOR
³¹Group, CR³⁰= NN (R¹²) R¹³Group, CR³⁰(Z
^TwoR³²)_TwoGroup, COOR^{twenty two}Group, CH_TwoOR^TenGroup, CR^{twenty three}=
CR^{twenty four}COOR^{twenty five}Group or CH_TwoCHWCOOR^{twenty five}Base
Represent.

Wherein R ¹² and R ¹³ have the same meaning as described above, W represents a hydrogen atom, a chlorine atom or a bromine atom;
R ⁹ represents a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group or a C3-C6 alkenyl group, and R ¹¹ represents a C1-C6 alkyl group, a C3-
Represents a C8 cycloalkyl group or a C3-C6 alkenyl group, and R ²¹ is a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C6 alkenyl group, a C3-C6 haloalkenyl group, a C3- C6
R ²² represents a hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a benzyl group, a C3-C6 alkenyl group, a C3-C6 alkenyl group, −
C6 haloalkenyl group, C3-C6 alkynyl group, C3
-C6 haloalkynyl group, cyano C1-C6 alkyl group, C1-C4 alkoxy C1-C4 alkyl group, C1
-C4 alkylthio C1-C4 alkyl group, carboxy C1-C6 alkyl group, (C1-C8 alkoxy) carbonyl C1-C6 alkyl group, (C1-C6 haloalkoxy) carbonyl C1-C6 alkyl group, {(C1-C
4 alkoxy) C1-C4 alkoxy @ carbonyl C1
-C6 alkyl group, (C3-C8 cycloalkoxy) carbonyl C1-C6 alkyl group, (C1-C6 alkyl) carbonyl C1-C6 alkyl group, (C1-C6 haloalkyl) carbonyl C1-C6 alkyl group, {(C
1-C4 alkoxy) C1-C4 alkyl} carbonyl C1-C6 alkyl group, (C3-C8 cycloalkyl)
Carbonyl C1-C6 alkyl group, -CH ₂ COON
(R ²⁶⁾ R ²⁷ group, -CH (C1-C4 alkyl) COO
N (R ²⁶⁾ R ^{27 _{group, -CH 2 CON (R 26)}} R 27 group, -
CH (C1-C4 alkyl) CON (R ²⁶⁾ R ²⁷ group (herein, R ²⁶ and R ²⁷ are the same or different and a hydrogen atom, C
1-C6 alkyl group, C1-C6 haloalkyl group, C3
-C6 alkenyl group, C3-C6 alkynyl group, cyano C1-C6 alkyl group, C1-C4 alkoxy C1-C
4 alkyl groups, C1-C4 alkylthio C1-C4 alkyl groups, carboxy C1-C6 alkyl groups, (C1-C4
6 alkoxy) carbonyl C1-C6 alkyl group, (C
3-C8 cycloalkoxy) carbonyl C1-C6 alkyl group or {(C1-C4 alkoxy) C1-C4
Alkyl} or a carbonyl C1-C6 alkyl, or represents a tetramethylene, pentamethylene or ethyleneoxyethylene between R ²⁶ and R ^27. ), {(C1
—C6 alkoxy) carbonyl C1-C6 alkyl} oxycarbonyl represents a C1-C6 alkyl group or a hydroxy C2-C6 alkyl group, and R ²³ and R ²⁴ are the same or different and are a hydrogen atom, a halogen atom or C1-C6
Represents an alkyl group, R ²⁵ represents a hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group or a C3-C6 alkenyl group, and R ²⁸ and R ²⁹ are the same or different from each other; C6 alkyl group, C
1-C6 haloalkyl group, or represents a phenyl group which may be substituted with a methyl group or a nitro group, R ³⁰
Represents a hydrogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group or a C2-C6 alkynyl group, and R ³¹ represents a hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C6 alkenyl group, a C3- C6 haloalkenyl group, C3-C6 alkynyl group, cyano C1-C6 alkyl group, C1-C4 alkoxy C1-C4 alkyl group, C1-C4 alkylthio C1-C4 alkyl group, carboxy C1-C6 alkyl group, (C1-C6 alkoxy group ) Carbonyl C1-C6 alkyl group, (C3-C8 cycloalkoxy) carbonyl C1-C6 alkyl group or {(C1-C4 alkoxy) C1-C4 alkoxy}
Represents a carbonyl C1-C6 alkyl group, wherein R ³² is C1-
Represents a C6 alkyl group or a C3-C6 alkenyl group.

R ¹⁰ is a hydrogen atom, a C1-C6 alkyl group,
C1-C6 haloalkyl group, C3-C8 cycloalkyl group, benzyl group, C3-C6 alkenyl group, C3-C6
Haloalkenyl group, C3-C6 alkynyl group, C3-C
6 haloalkynyl group, cyano C1-C6 alkyl group, C
1-C4 alkoxy C1-C4 alkyl group, C1-C4
Alkylthio C1-C4 alkyl group, carboxy C1-
C6 alkyl group, (C1-C8 alkoxy) carbonyl C1-C6 alkyl group, (C1-C6 haloalkoxy)
Carbonyl C1-C6 alkyl group, {(C1-C4 alkoxy) C1-C4 alkoxy} carbonyl C1-C6
Alkyl group, (C3-C8 cycloalkoxy) carbonyl C1-C6 alkyl group, (C3-C8 cycloalkyl) C1-C6 alkoxycarbonyl C1-C6 alkyl ^{_{group, -CH 2 COON (R 12)}} R 13 group, -CH ( C1
—C4 alkyl) COON (R ¹² ) R ¹³ group, —CH ₂ C
ON (R ¹² ) R ¹³ group, —CH (C1-C4 alkyl) C
An ON (R ¹² ) R ¹³ group (where R ¹² and R ¹³ represent the same meaning as described above), a C2-C6 alkenyloxycarbonyl C1-C6 alkyl group, a C3-C6 haloalkenyloxycarbonyl C1-C6 alkyl Group, C3-C6 alkynyloxycarbonyl C1-C6 alkyl group, C3-
C6 haloalkynyloxycarbonyl C1-C6 alkyl group, (C1-C6 alkylthio) carbonyl C1-C
6 alkyl groups, (C1-C6 haloalkylthio) carbonyl C1-C6 alkyl groups, (C3-C6 alkenylthio) carbonyl C1-C6 alkyl groups, (C3-C6 haloalkenylthio) carbonyl C1-C6 alkyl groups,
(C3-C6 alkynylthio) carbonyl C1-C6 alkyl group, (C3-C6 haloalkynylthio) carbonyl C1-C6 alkyl group, (C3-C8 cycloalkylthio) carbonyl C1-C6 alkyl group, (C3-C8
Cyclohaloalkylthio) carbonyl C1-C6 alkyl group, {(C3-C8 cycloalkyl) C1-C6 alkylthio} carbonyl C1-C6 alkyl group, di (C1
-C6 alkyl) C = NO carbonyl C1-C6 alkyl group, (optionally substituted benzylthio) carbonyl C1-C6 alkyl group, (optionally substituted phenylthio) carbonyl C1-C6 alkyl group, hydroxy C2-C6 Alkoxycarbonyl C1-C6 alkyl group, (C1-C6 alkyl) carbonyloxy C2-C
6 alkoxycarbonyl C1-C6 alkyl group, (C1
-C6 alkyl) carbonylamino C2-C6 alkoxycarbonyl C1-C6 alkyl group, {(C1-C6 alkoxy) carbonyl C1-C6 alkyl} oxycarbonyl C1-C6 alkyl group, hydroxy C2-C6 alkyl group, C1-C6 alkoxycarbonyl Group, C1-
C6 haloalkoxycarbonyl group, C3-C8 cycloalkoxycarbonyl group, C3-C6 alkenyloxycarbonyl group, benzyloxycarbonyl group which may be substituted, C1-C6 alkylcarbonyl group, C3-C
6-alkenylcarbonyl group, benzyloxycarbonyl C1-C6 alkyl group which may be substituted, phenoxycarbonyl C1-C6 alkyl group which may be substituted, furyloxycarbonyl C1 which may be substituted
-C6 alkyl group, optionally substituted furyl C1-
A C6 alkyloxycarbonyl C1-C6 alkyl group,
Optionally substituted thienyloxycarbonyl C1-
C6 alkyl group, optionally substituted thienyl C1-
A C6 alkyloxycarbonyl C1-C6 alkyl group,
Optionally substituted pyrrolyloxycarbonyl C1-
C6 alkyl group, optionally substituted pyrrolyloxy C1-C6 alkyloxycarbonyl C1-C6 alkyl group, optionally substituted imidazoyloxycarbonyl C1-C6 alkyl group, optionally substituted imidazoyl C1-C6 alkyl Oxycarbonyl C1-C
6-alkyl group, optionally substituted pyrazoyloxycarbonyl C1-C6 alkyl group, optionally substituted pyrazoyl C1-C6 alkyloxycarbonyl C1
-C6 alkyl group, optionally substituted thiazoyloxycarbonyl C1-C6 alkyl group, optionally substituted thiazoyl C1-C6 alkyloxycarbonyl C1-C6 alkyl group, optionally substituted oxazoyloxycarbonyl C1-C6 alkyl group, optionally substituted oxazoyl C1-C6 alkyloxycarbonyl C1-C6 alkyl group, optionally substituted isothiazoyloxycarbonyl C1-C6 alkyl group, optionally substituted isothiazoyl C1 -C6 alkyloxycarbonyl C1-C6 alkyl group, optionally substituted isoxazoyloxycarbonyl C1-
C6 alkyl group, optionally substituted isoxazoyl C1-C6 alkyloxycarbonyl C1-C6 alkyl group, optionally substituted pyridyloxycarbonyl C1-C6 alkyl group, optionally substituted pyridyl C1-C6 alkyloxy Carbonyl C1-C6 alkyl group, optionally substituted pyrazinyloxycarbonyl C1-C6 alkyl group, optionally substituted pyrazinyl C1-C6 alkyloxycarbonyl C1-C6 alkyl group, optionally substituted pyrimidinyl An oxycarbonyl C1-C6 alkyl group, an optionally substituted pyrimidinyl C1-C6 alkyloxycarbonyl C1
-C6 alkyl group, optionally substituted pyridazinyloxycarbonyl C1-C6 alkyl group, optionally substituted pyridazinyl C1-C6 alkyloxycarbonyl C1-C6 alkyl group, optionally substituted indolizini Oxycarbonyl C1-C6 alkyl group, optionally substituted indolizinyl C1-C6 alkyloxycarbonyl C1-C6 alkyl group, optionally substituted indolyloxycarbonyl C1-C6 alkyl group, optionally substituted Indolyl C1-C6 alkyloxycarbonyl C1-C6 alkyl group, optionally substituted indazolyloxycarbonyl C1-C6
Alkyl group, optionally substituted indazolyl C1-
A C6 alkyloxycarbonyl C1-C6 alkyl group,
Optionally substituted quinolyloxycarbonyl C1-
C6 alkyl group, optionally substituted quinolyl C1-
A C6 alkyloxycarbonyl C1-C6 alkyl group,
Optionally substituted isoquinolyloxycarbonyl C
A 1-C6 alkyl group or an optionally substituted isoquinolyl C1-C6 alkyloxycarbonyl C1-C
6 represents an alkyl group, or

Embedded image Wherein R ¹⁴ represents a hydrogen atom or a C1-C5 alkyl group, and R ¹⁵ represents a hydrogen atom, a hydroxyl group or —O—C
A group represented by OR ¹⁶ (R ¹⁶ is a C1-C6 alkyl group,
A C1-C6 haloalkyl group, a C3-C6 alkenyl group,
A C3-C8 cycloalkyl group, an optionally substituted phenyl group, an optionally substituted benzyl group or C1
-C6 represents an alkoxy group. ). Or a group represented by the general formula

Embedded image<Where R¹⁷Is a hydrogen atom, a halogen atom or C1-C
6 represents an alkyl group; ¹⁸Is C3-C8 cycloalkyl
C2 -C having a group, a benzyl group and an epoxy group on the carbon chain
10 alkyl groups, C3-C8 cycloalkyl C1-C6
Alkyl group, C3-C8 cycloalkyl C2-C6 alkyl
Kenyl group, the same carbon atom is OR¹⁹Group and OR²⁰Base
A substituted C1-C6 alkyl group, wherein the same carbon atom is OR
¹⁹Group and OR²⁰-C6 alkenyl substituted with a group
Group, the same carbon atom is SR¹⁹Group and SR²⁰Substituted with a group
C1-C6 alkyl group, the same carbon atom is SR¹⁹Basis
And SR ²⁰C2-C6 alkenyl group substituted with a group (here
And R¹⁹And R²⁰Are the same or different C1-C6 alkyl
Or a C1-C6 haloalkyl group,¹⁹And R²⁰
And ethylene optionally substituted with a halogen atom,
Trimethylene, ha which may be substituted with a halogen atom;
Tetramethylene, ha
Pentamethylene which may be substituted with a
Is ethyleneoxy optionally substituted with a halogen atom
Represents ethylene. ), Carboxy C2-C6 alkenyl
Group, (C1-C8 alkoxy) carbonyl C2-C6
Lucenyl group, (C1-C8 haloalkoxy) carbonyl
C2-C6 alkenyl group, ｛(C1-C4 alkoxy)
C1-C4 alkoxy @ carbonyl C2-C6 alkenyl
Group, (C3-C8 cycloalkoxy) carbonyl C2
-C6 represents an alkenyl group. >. }]
Any of Q-1, Q-2, Q-3, Q-4 or Q-5
Is raised,

The C1-C6 alkyl group represented by R ¹ includes a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group and a t-butyl group (where "t" is [tertiary] In the following, the same applies), amyl group,
Isoamyl group and the like, C1-C3 represented by R ²
Examples of the alkyl group include a methyl group and an ethyl group. Examples of the C1-C3 haloalkyl group represented by R ³ include a trifluoromethyl group, a chlorodifluoromethyl group, and a difluoromethyl group. Examples of the halogen atom include a fluorine atom, a chlorine atom, and a bromine atom. Examples of the halogen atom represented by Y include a fluorine atom, a chlorine atom, and a bromine atom.
Examples of the C1-C3 alkyl group represented by R ⁴ include a methyl group, and examples of the C1-C6 alkyl group represented by R ⁵ include a methyl group, an ethyl group, a propyl group, an isopropyl group, an isobutyl group, and a butyl group. , T-butyl group,
Examples thereof include an isoamyl group, and examples of the C1-C6 haloalkyl group include a 2-fluoroethyl group, a 2-chloroethyl group, a 2-bromoethyl group, a 3-chlorobutyl group, a 3-bromobutyl group, and a difluoromethyl group. C
Examples of the 3-C8 cycloalkyl) C1-C6 alkyl group include a cyclopentylmethyl group and a cyclohexylmethyl group, and examples of the C3-C6 alkenyl group include an allyl group, a 1-methyl-2-propenyl group, and a 3-butenyl group. , 2-butenyl group, 3-methyl-2-butenyl group, 2
-Methyl-3-butenyl group and the like, and the C3-C6 haloalkenyl group include a 2-chloro-2-propenyl group and a 3,3-dichloro-2-propenyl group, and a C3-C6 alkynyl group. As a propargyl group, a 1-methyl-2-propynyl group, a 2-butynyl group,
3-butynyl group, 1,1-dimethyl-2-propynyl group and the like, and as the C3-C6 haloalkynyl group,
3-chloro-2-propynyl group, 3-bromo-2-propynyl group and the like, and cyano C1-C6 alkyl group include cyanomethyl group and cyanoethyl group, and C1-C4 alkoxy C1-C4 alkyl group. Examples thereof include a methoxymethyl group, a 1-methoxyethyl group, an ethoxymethyl group and the like, and a C1-C3 alkoxy C1-
Examples of the C3 alkoxy C1-C3 alkyl group include a methoxymethoxymethyl group, a methoxyethoxymethyl group, and an ethoxymethoxymethyl group.
Examples of the 6 alkyl group include a carboxymethyl group, a 1-carboxyethyl group, and a 2-carboxyethyl group. Examples of the (C1-C6 alkoxy) carbonyl C1-C6 alkyl group include a methoxycarbonylmethyl group and an ethoxycarbonylmethyl group. , Propoxycarbonylmethyl group, isopropoxycarbonylmethyl group, butoxycarbonylmethyl group, isobutoxycarbonylmethyl group, t
-Butoxycarbonylmethyl group, amyloxycarbonylmethyl group, isoamyloxycarbonylmethyl group, t
-Amyloxycarbonylmethyl group, 1-methoxycarbonylethyl group, 1-ethoxycarbonylethyl group, 1
-Propoxycarbonylethyl group, 1-isopropoxycarbonylethyl group, 1-butoxycarbonylethyl group, 1-isobutoxycarbonylethyl group, 1-t-butoxycarbonylethyl group, 1-amyloxycarbonylethyl group, 1-isoamyloxy Carbonylethyl group, 1-t-butoxycarbonylethyl group and the like, and {(C1-C4 alkoxy) C1-C4 alkoxy} carbonyl C1-C6 alkyl group includes methoxyethoxycarbonylmethyl group, 1-methoxymethoxycarbonylethyl And the (C3-C8 cycloalkoxy) carbonyl C1-C6 alkyl group includes a cyclobutyloxycarbonylmethyl group, a cyclopentyloxycarbonylmethyl group, a cyclohexyloxycarbonylmethyl group, a 1- Examples thereof include chlorobutyloxycarbonylethyl group, 1-cyclopentyloxycarbonylethyl group, and 1-cyclohexyloxycarbonylethyl group. Examples of the C1-C4 alkylthio C1-C4 alkyl group include a methylthiomethyl group, a 1-methylthioethyl group, and ethyl. A thiomethyl group and the like, and the hydroxy C1-C6 alkyl group includes a hydroxymethyl group,
Hydroxyethyl group, hydroxypropyl group and the like,

The C1-C6 alkyl group represented by R ⁶ includes a methyl group and an ethyl group, and the C1-C6 haloalkyl group includes a bromomethyl group, a dibromomethyl group, a tribromomethyl group, a 1-bromoethyl group, Examples thereof include a chloromethyl group, a dichloromethyl group, and a trichloromethyl group. Examples of the hydroxy C1-C6 alkyl group include a hydroxymethyl group and a 2-hydroxyethyl group. As the (C1-C6 alkoxy) C1-C6 alkyl group, Represents a methoxymethyl group, an ethoxymethyl group, a propoxymethyl group, an isopropoxymethyl group, and the like.
Examples of the 1-C6 alkoxy C1-C6 alkoxy C1-C6 alkyl group include a methoxymethoxymethyl group, a methoxyethoxymethyl group, an ethoxymethoxymethyl group, and the like, and (C1-C6 alkyl) carbonyloxy C1
As the -C6 alkyl group, an acetyloxymethyl group,
Examples include an ethylcarbonyloxymethyl group and an isopropylcarbonyloxymethyl group, and the (C1-C6 haloalkyl) carbonyloxy C1-C6 alkyl group includes a trifluoroacetyloxymethyl group, a chloroacetyloxymethyl group, and a trichloroacetyloxymethyl group. Examples of the (C1-C6 alkoxy) carbonyl group include a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a butoxycarbonyl group, an amyloxycarbonyl group, an isopropoxycarbonyl group, an isobutoxycarbonyl group, and an isoamyloxycarbonyl group. And C1-C6 represented by R ^7.
Examples of the alkyl group include a methyl group and an ethyl group.

The C1-C6 alkyl group represented by R ⁸ includes a methyl group and an ethyl group, and the C1-C6 haloalkyl group includes a chloromethyl group and a bromomethyl group. Examples of the group include a hydroxymethyl group and the like. Examples of the C1-C4 alkoxy C1-C4 alkyl group include a methoxymethyl group, an ethoxymethyl group, an isopropoxymethyl group, a butoxymethyl group, an isobutoxymethyl group, and the like.
Examples of the 1-C3 alkoxy C1-C3 alkoxy C1-C3 alkyl group include a methoxymethoxymethyl group, a methoxyethoxymethyl group, an ethoxymethoxymethyl group and the like, and a (C1-C6 alkyl) carbonyloxy C1-alkyl group.
Examples of the C6 alkyl group include an acetyloxymethyl group, an ethylcarbonyloxymethyl group, and an isopropylcarbonyloxymethyl group. Examples of the (C1-C6 haloalkyl) carbonyl C1-C6 alkyl group include a 2-chloroethylcarbonyloxymethyl group. Examples of the carboxy C1-C6 alkyl group include a carboxymethyl group and a carboxyethyl group. Examples of the (C1-C8 alkoxy) carbonyl group include a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group,
Butoxycarbonyl group, amyloxycarbonyl group, t
-Butoxycarbonyl group, isopropoxycarbonyl group, isobutoxycarbonyl group, isoamyloxycarbonyl group, t-amyloxycarbonyl group and the like. Examples of the (C1-C6 haloalkoxy) carbonyl group include 2-chloroethoxycarbonyl group, -Bromoethoxycarbonyl group, 3-chlorobutoxycarbonyl group, 1
-Chloro-2-propoxycarbonyl group, 1,3-dichloro-2-propoxycarbonyl group, 2,2-dichloroethoxycarbonyl group, 2,2,2-trifluoroethoxycarbonyl group, 2,2,2-trichloroethoxy A carbonyl group, a 2,2,2-tribromoethoxycarbonyl group and the like, and (C3-C10 cycloalkoxy)
Examples of the carbonyl group include a cyclobutyloxycarbonyl group, a cyclopentyloxycarbonyl group, and a cyclohexyloxycarbonyl group. Examples of the (C3-C8 alkenyloxy) carbonyl group include an allyloxycarbonyl group, a 3-butenyloxycarbonyl group, and And a methyl-2-propenyloxycarbonyl group.
Examples of the (C3-C8 alkynyloxy) carbonyl group include a propargyloxycarbonyl group, a 3-butynyloxycarbonyl group, a 1-methyl-2-propynyloxycarbonyl group, and a (C1-C6 alkyl) aminocarbonyl group. , A methylaminocarbonyl group, an ethylaminocarbonyl group and the like, and di (C1-C6
Examples of the alkyl) aminocarbonyl group include a dimethylaminocarbonyl group, a diethylaminocarbonyl group, a diisopropylaminocarbonyl group, and the like.
Examples of the alkyl) aminocarbonyloxy C1-C6 alkyl group include a methylaminocarbonyloxymethyl group, and examples of the di (C1-C6 alkyl) aminocarbonyloxy C1-C6 alkyl group include a dimethylaminocarbonyloxymethyl group and diethylamino. And a carbonyloxymethyl group.

Examples of the halogen atom represented by B include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom. Examples of the C1-C6 alkyl group represented by R ⁹ include a methyl group, an ethyl group, a propyl group, Isopropyl, butyl, isobutyl, t-butyl and the like;
Examples of the -C6 haloalkyl group include a chloromethyl group, a trichloromethyl group and a trifluoromethyl group.
Examples of the 3-C8 cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group. Examples of the C3-C6 alkenyl group include an allyl group, a 1-methyl-2-propenyl group, and a 3-butenyl group. Group, 2-butenyl group, 3-methyl-2-butenyl group, 2-methyl-3-butenyl group and the like,

[0012] The C1-C6 alkyl group represented by R ^10, a methyl group, an ethyl group, a propyl group, an isopropyl group, an isobutyl group, butyl group, t- butyl group, amyl group, isoamyl group, t-amyl group and the like And C1-
As the C6 haloalkyl group, a 2-fluoroethyl group,
2-chloroethyl group, 2-bromoethyl group, 1,1,
Examples thereof include a 2,2-tetrafluoroethyl group and a 3-chloropropyl group. Examples of the C3-C8 cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group. Examples of the alkenyl group include an allyl group, a 1-methyl-2-propenyl group, a 3-butenyl group, a 2-butenyl group, a 3-methyl-2-butenyl group, a 2-methyl-3-butenyl group, and the like. -C6 haloalkenyl group includes 2
-Chloro-2-propenyl group, 3,3-dichloro-2-
And a C3-C6 alkynyl group such as a propargyl group, a 1-methyl-2-propynyl group, a 2-butynyl group, and a 1,1-dimethyl-2-propynyl group. Examples of the haloalkynyl group include a 3-bromopropargyl group and the like.
Examples of the -C6 alkynyl group include a cyanomethyl group, and examples of the C1-C4 alkoxy C1-C4 alkyl group include a methoxymethyl group, a methoxyethyl group, an ethoxymethyl group, and an ethoxyethyl group.
Examples of the alkylthio C1-C4 alkyl group include a methylthiomethyl group and a methylthioethyl group, and examples of the carboxy C1-C6 alkyl group include a carboxymethyl group, a 1-carboxyethyl group, and a 2-carboxyethyl group. (C1-C8 alkoxy) carbonyl C
Examples of the 1-C6 alkyl group include methoxycarbonylmethyl, ethoxycarbonylmethyl, propoxycarbonylmethyl, isopropoxycarbonylmethyl, butoxycarbonylmethyl, isobutoxycarbonylmethyl, t-butoxycarbonylmethyl, amyloxycarbonyl Methyl group, isoamyloxycarbonylmethyl group, t-amyloxycarbonylmethyl group, 1-methoxycarbonylethyl group, 1-ethoxycarbonylethyl group, 1-propoxycarbonylethyl group, 1-isopropoxycarbonylethyl group, 1-butoxycarbonyl Ethyl group, 1-isobutoxycarbonylethyl group, 1
-T-butoxycarbonylethyl group, 1-amyloxycarbonylethyl group, 1-isoamyloxycarbonylethyl group, 1-t-butoxycarbonylethyl group, 1-
Examples thereof include an amyloxycarbonylethyl group, a 1-isoamyloxycarbonylethyl group, a 1-t-amyloxycarbonylethyl group, and a (C1-C6 haloalkoxy) carbonyl C1-C6 alkyl group includes 2-chloroethoxycarbonylmethyl. Group, 2,2,2-trifluoroethoxycarbonylmethyl group and the like,
{(C1-C4 alkoxy) C1-C4 alkoxy} carbonyl C1-C6 alkyl groups include methoxymethoxycarbonylmethyl, methoxyethoxycarbonylmethyl, 1-methoxyethoxycarbonylethyl and the like. Examples of the alkoxy) carbonyl C1-C6 alkyl group include a cyclobutyloxycarbonylmethyl group, a cyclopentyloxycarbonylmethyl group, a cyclohexyloxycarbonylmethyl group,
1-cyclobutyloxycarbonylethyl group, 1-cyclopentyloxycarbonylethyl group, 1-cyclohexyloxycarbonylethyl group and the like, and C2-C
As the 6-alkenyloxycarbonyl C1-C6 alkyl group, a vinyloxycarbonylmethyl group, an allyloxycarbonylmethyl group, a (1-methyl-2-propenyloxycarbonyl) methyl group, a 1-allyloxycarbonylethyl group, a 1- (1 -Methyl-2-propenyloxycarbonyl) ethyl group and the like. Examples of the C3-C6 haloalkenyloxycarbonyl C1-C6 alkyl group include a 3,3-dichloro-2-propenyloxymethyl group and the like. Examples of the C6 alkynyloxycarbonyl C1-C6 alkyl group include a propargyloxycarbonylmethyl group, a (1-methyl-2-propynyloxycarbonyl) methyl group, a (3-butynyloxycarbonyl) methyl group, a (1,1-dimethyl- 2-propynyloxycarboni ) Methyl group, 1- (propargyloxycarbonyl) ethyl group, 1- (1-methyl-2-propynyloxycarbonyl) ethyl group, 1- (3-butynyloxycarbonyl) ethyl group, 1- (1,1- And a C3-C6 haloalkynyloxycarbonyl C1-C6 alkyl group such as a (3-chloro-2-propenyloxycarbonyl) methyl group and a 2- (3 -Chloro-2-propenyloxycarbonyl) ethyl group and the like, and (C1-C6 alkylthio) carbonyl C1-
Examples of the C6 alkyl group include a methylthiocarbonylmethyl group, an ethylthiocarbonylmethyl group, a propylthiocarbonylmethyl group, an isopropylthiocarbonylmethyl group, a 1- (methylthiocarbonyl) ethyl group, a 1- (ethylthiocarbonyl) ethyl group, (Propylthiocarbonyl) ethyl group, 1- (isopropylthiocarbonyl) ethyl group and the like. Examples of the (optionally substituted benzylthio) carbonyl C1-C6 alkyl group include benzylthiocarbonylmethyl group and (4-methyl A benzylthiocarbonyl) methyl group, a 1-benzylthiocarbonylethyl group, a 1- (4-methylbenzylthiocarbonyl) ethyl group, and the like. Examples of the (optionally substituted phenylthio) carbonyl C1-C6 alkyl group include: Phenylthioca Bonylmethyl group, 1-phenylthiocarbonylethyl group 2-phenylthiocarbonylethyl and the like, and as the hydroxy C2-C6 alkoxycarbonyl C1-C6 alkyl group, 2-hydroxyethoxycarbonylmethyl group, 3-hydroxycarbonylpropoxycarbonylmethyl group , 1- (2-hydroxyethoxycarbonyl) ethyl group, 1- (3-hydroxycarbonylpropoxycarbonyl) ethyl group and the like, and (C1-C6 alkyl) carbonyloxy C2-
As the C6 alkoxycarbonyl C1-C6 alkyl group, a 2-acetyloxyethoxycarbonylmethyl group,
1- (2-acetyloxycarbonyl) ethyl group and the like, and (C1-C6 alkyl) carbonylamino C2
Examples of the -C6 alkoxycarbonyl C1-C6 alkyl group include a 2-acetylaminoethoxycarbonylmethyl group and a 1- (acetylaminoethoxycarbonyl) ethyl group. Examples of the hydroxy C2-C6 alkyl group include a 2-hydroxyethyl group. And 3-hydroxypropyl groups. Examples of the C1-C6 alkoxycarbonyl group include methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, isobutoxycarbonyl, and t-butoxycarbonyl. Group, amyloxycarbonyl group, isoamyloxycarbonyl group, t-amyloxycarbonyl group and the like. Examples of the C3-C6 cycloalkoxycarbonyl group include a cyclobutyloxycarbonyl group and a cyclopentyl group. And a C3-C6 alkenyloxycarbonyl group such as an allyloxycarbonyl group and a 1-methyl-2-propenyloxycarbonyl group, which may be substituted. Examples of the benzyloxycarbonyl group include a benzyloxycarbonyl group, and examples of the C1-C6 alkylcarbonyl group include an acetyl group, a trimethylacetyl group, an ethylcarbonyl group, and an isopropylcarbonyl group, which may be substituted. Benzyloxycarbonyl C1-C
Examples of the 6 alkyl group include a benzyloxycarbonylmethyl group, a 1-benzyloxycarbonylethyl group and the like, and an optionally substituted phenoxycarbonyl C1
Examples of the -C6 alkyl group include a phenoxycarbonylmethyl group and a 1-phenoxycarbonylethyl group.

[0013] The C1-C6 alkyl group represented by R ¹² and R ^13, a methyl group, an ethyl group, a propyl group, an isopropyl group, butyl group, isobutyl group and the like, C
Examples of the 3-C8 cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group. Examples of the C1-C6 haloalkyl group include a 2-fluoroethyl group, a 2-chloroethyl group, and a 2-chloroethyl group.
A bromoethyl group and the like; examples of the C3-C6 alkenyl group include an allyl group, a 1-methyl-2-propenyl group, a 3-butenyl group, a 2-butenyl group and a 3-methyl-2 group;
-Butenyl group, 2-methyl-3-butenyl group and the like. Examples of the C3-C6 alkynyl group include a propargyl group, a 1-methyl-2-propynyl group, a 2-butynyl group,
1,1-dimethyl-2-propynyl group and the like, and as the cyano C1-C6 alkyl group, a cyanomethyl group,
2-Cyanoethyl group and the like, and as the C1-C4 alkoxy C1-C4 alkyl group, a methoxymethyl group,
A methoxyethyl group, an ethoxymethyl group, an ethoxyethyl group and the like can be mentioned, examples of the C1-C4 alkylthio C1-C4 alkyl group include a methylthiomethyl group and a methylthioethyl group, and examples of the carboxy C1-C6 alkyl group include a carboxy A methyl group, a 1-carboxyethyl group, a 2-carboxyethyl group and the like, and (C1-C
6 alkoxy) carbonyl C1-C6 alkyl group includes methoxycarbonylmethyl group, ethoxycarbonylmethyl group, propoxycarbonylmethyl group, isopropoxycarbonylmethyl group, butoxycarbonylmethyl group, isobutoxycarbonylmethyl group, t-butoxycarbonylmethyl group , Amyloxycarbonylmethyl group,
Isoamyloxycarbonylmethyl group, t-amyloxycarbonylmethyl group, 1-methoxycarbonylethyl group, 1-ethoxycarbonylethyl group, 1-propoxycarbonylethyl group, 1-isopropoxycarbonylethyl group, 1-butoxycarbonylethyl group, 1-isobutoxycarbonylethyl group, 1-t-butoxycarbonylethyl group, 1-amyloxycarbonylethyl group, 1
-Isoamyloxycarbonylethyl group, 1-t-butoxycarbonylethyl group, 1-amyloxycarbonylethyl group, 1-isoamyloxycarbonylethyl group,
1-t-amyloxycarbonylethyl group and the like, and (C3-C8 cycloalkoxy) carbonyl C1-
Examples of the C6 alkyl group include cyclobutyloxycarbonylmethyl, cyclopentyloxycarbonylmethyl, cyclohexyloxycarbonylmethyl, 1-cyclobutyloxycarbonylethyl, 1-cyclopentyloxycarbonylethyl, 1-cyclohexyloxycarbonylethyl, and the like. Examples of the (C1-C6 alkyl) carbonyloxy C2-C6 alkyl group include a methylcarbonyloxyethyl group, an ethylcarbonyloxyethyl group, and the like, and a (C1-C6 alkyl) carbonylamino C2-C6 alkyl group Is
A methylcarbonylaminoethyl group, an ethylcarbonylaminoethyl group and the like can be mentioned, and the hydroxy C2-C6 alkyl group includes a hydroxyethyl group and a hydroxypropyl group, and the optionally substituted benzyl group includes a benzyl group. And the phenyl group which may be substituted includes a phenyl group.
The {(C1-C4 alkoxy) C1-C4 alkyl} carbonyl C1-C6 alkyl group, methoxy methoxycarbonylmethyl group, 1-methoxy-methoxycarbonylethyl group and the like, as C1-C5 alkyl group represented by R ¹⁴ Is a methyl group, an ethyl group, etc.,

[0014] The C1-C6 alkyl group represented by R ^16, a methyl group, an ethyl group, a propyl group, an isopropyl group, butyl group, isobutyl group and the like, C1-C6
Examples of the haloalkyl group include a trifluoromethyl group and the like, and examples of the C3-C6 alkenyl group include an allyl group, a 1-methyl-2-propenyl group, a 3-butenyl group,
Examples thereof include a 2-butenyl group, a 3-methyl-2-butenyl group, and a 2-methyl-3-butenyl group. Examples of the C3-C8 cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group. Examples of the optionally substituted phenyl group include a phenyl group, and the optionally substituted benzyl group include a benzyl group. The C1-C6 alkoxy group includes a methoxy group, Ethoxy groups and the like,
Examples of the halogen atom represented by R ¹⁷ include a chlorine atom and a bromine atom. Examples of the C1-C6 alkyl group include a methyl group. Examples of the C3-C8 cycloalkyl group represented by R ¹⁸ include cycloalkyl. A propyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group and the like; and a C2-C10 alkyl group having an epoxy group in the carbon chain include an oxiranyl group and an oxiranylmethyl group; Examples of the C6 alkyl group include a cyclopentylmethyl group, a cyclohexylmethyl group, a 2-cyclopropylethyl group, and a cyclobutylmethyl group.
Examples of the 2-C6 alkenyl group include a 3-cyclopentylallyl group, and examples of the carboxy C2-C6 alkenyl group include a 2-carboxyvinyl group and a 3-carboxyallyl group, and (C1-C8 alkoxy) carbonyl C2 -C6 alkenyl groups include 2-methoxycarbonylvinyl, 2-ethoxycarbonylvinyl and 3
-Methoxycarbonylallyl group, 3-ethoxycarbonylallyl group and the like, and (C1-C8 haloalkoxy) carbonyl C2-C6 alkenyl group is 2-
(2-fluoroethoxy) carbonyl vinyl group, 3- (2
-Fluoroethoxy) carbonyl allyl group and the like, and {(C1-C4 alkoxy) C1-C4 alkoxy} carbonyl C2-C6 alkenyl group is 2-
(2-methoxyethoxy) carbonylvinyl group, 3-
(2-methoxyethoxy) carbonyl allyl group and the like, and (C3-C6 cycloalkoxy) carbonyl C2
Examples of the -C6 alkenyl group include a 2-cyclopentyloxycarbonylvinyl group, a 2-cyclohexyloxycarbonylvinyl group, a 3-cyclopentyloxycarbonylallyl group, and a 3-cyclohexyloxycarbonylallyl group.

Examples of the C1-C6 alkyl group in which the same carbon atom is substituted with a OR ¹⁹ group and OR ²⁰ group -CH (OR
¹⁹⁾ (OR ^{20) _{group, -CH 2 CH (OR 19)}} (OR 20)
And the same carbon atom is a group consisting of SR ¹⁹ and SR ²⁰
A C1-C6 alkyl group substituted with a group
(SR ¹⁹ ) (SR ²⁰ ) group, —CH ₂ CH (SR ¹⁹ ) (S
R ²⁰⁾ group and the like, represented by R ¹⁹ and R ²⁰ C1-
Examples of the C6 alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group and an isobutyl group, and examples of the C1-C6 haloalkyl group include a 2-chloroethyl group and a 2-fluoroethyl group. , R ¹¹
As the C1-C6 alkyl group represented by, a methyl group,
Ethyl group, isopropyl group and the like, C3-C8 cycloalkyl group includes cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group and the like, and C3-C6 alkenyl group includes allyl group,
1-methyl-2-propenyl group, 3-butenyl group, 2-
Butenyl, 3-methyl-2-butenyl group, 2-methyl-3-butenyl group and the like, represented by R ²¹ C1-
Examples of the C6 alkyl group include a methyl group, an ethyl group, a propyl group, and an isopropyl group. Examples of the C1-C6 haloalkyl group include a 2,2,2-trifluoroethyl group, a 2-chloroethyl group, and a 2-bromoethyl group. Examples of the C3-C8 cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group. Examples of the C3-C6 alkenyl group include an allyl group and 1-methyl-2-propenyl. Group, 3
-Butenyl group, 2-butenyl group, 3-methyl-2-butenyl group, 2-methyl-3-butenyl group and the like;
As the haloalkenyl group for 3-C6, 2-chloro-2
-Propenyl group, 3,3-dichloro-2-propenyl group and the like. Examples of the C3-C6 alkynyl group include a propargyl group, a 1-methyl-2-propynyl group, a 2-butynyl group, and a 1,1-dimethyl- group. 2-propynyl group and the like, and the C3-C6 haloalkynyl group include a 3-bromopropargyl group and the like.

Examples of the C1-C6 alkyl group represented by R ^22, a methyl group, an ethyl group, a propyl group, an isopropyl group, an isobutyl group, butyl group, t- butyl group, amyl group, isoamyl group, t-amyl group and the like And C1-
As the C6 haloalkyl group, 2-chloroethyl group, 2
-Bromoethyl group, 2,2,2-trifluoroethyl group and the like, and as the C3-C8 cycloalkyl group,
A cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and the like. Examples of the C3-C6 alkenyl group include an allyl group, a 1-methyl-2-propenyl group, a 3-butenyl group, a 2-butenyl group, and a 3-methyl group. −
Examples thereof include a 2-butenyl group and a 2-methyl-3-butenyl group, and examples of the C3-C6 haloalkenyl group include a 2-chloro-2-propenyl group and a 3,3-dichloro-2-propenyl group. , A C3-C6 alkynyl group includes a propargyl group, a 1-methyl-2-propynyl group,
Examples thereof include a 1,1-dimethyl-2-propynyl group and a 2-butynyl group. Examples of the C3-C6 haloalkynyl group include:
Examples thereof include a 3-chloropropargyl group and a 3-bromopropargyl group. Examples of the cyano C1-C6 alkyl group include:
A cyanomethyl group and a 2-cyanoethyl group;
Examples of the 1-C4 alkoxy C1-C4 alkyl group include a methoxymethyl group, a methoxyethyl group, an ethoxymethyl group, and an ethoxyethyl group. Examples of the C1-C4 alkylthio C1-C4 alkyl group include a methylthioethyl group. Examples of the carboxy C1-C6 alkyl group include a carboxymethyl group, a 1-carboxyethyl group, a 2-carboxyethyl group, and the like.
8 alkoxy) carbonyl C1-C6 alkyl groups include methoxycarbonylmethyl, ethoxycarbonylmethyl, propoxycarbonylmethyl, isopropoxycarbonylmethyl, butoxycarbonylmethyl, isobutoxycarbonylmethyl, t-butoxycarbonylmethyl , Amyloxycarbonylmethyl group,
Isoamyloxycarbonylmethyl group, t-amyloxycarbonylmethyl group, 1-methoxycarbonylethyl group, 1-ethoxycarbonylethyl group, 1-propoxycarbonylethyl group, 1-isopropoxycarbonylethyl group, 1-butoxycarbonylethyl group, 1-isobutoxycarbonylethyl group, 1-t-butoxycarbonylethyl group, 1-amyloxycarbonylethyl group, 1
-Isoamyloxycarbonylethyl group, 1-t-butoxycarbonylethyl group, 1-amyloxycarbonylethyl group, 1-isoamyloxycarbonylethyl group,
And a (C1-C6 haloalkoxy) carbonyl C1-C1 group.
6 alkyl groups include a 2-chloroethoxycarbonylmethyl group, a 3-chloropropoxycarbonylmethyl group,
1- (2-chloroethoxycarbonyl) ethyl group, 1-
(2-bromoethoxycarbonyl) ethyl group and the like. {(C1-C4 alkoxy) C1-C4 alkoxy} carbonyl C1-C6 alkyl group includes methoxymethoxycarbonylmethyl group, methoxyethoxycarbonylmethyl group, 1- ( Methoxyethoxycarbonyl)
Examples of the (C3-C8 cycloalkoxy) carbonyl C1-C6 alkyl group include a cyclobutyloxycarbonylmethyl group, a cyclopentyloxycarbonylmethyl group, a cyclohexyloxycarbonylmethyl group, and 1- (cyclobutyloxycarbonyl). Ethyl group, 1- (cyclopentyloxycarbonyl) ethyl group, 1- (cyclohexyloxycarbonyl) ethyl group and the like, and C1-C6 alkyl group represented by R ²³ and R ²⁴ include methyl group and the like. Examples of the C1-C6 alkyl group represented by ²⁵ include a methyl group, an ethyl group, a propyl group, an isopropyl group, an isobutyl group, a butyl group, a t-butyl group, an amyl group, an isoamyl group, and a t-amyl group. As the C1-C6 haloalkyl group, 2-chloroethyl , 2-bromoethyl group, 2,
2,2-trifluoroethyl group and the like, and C3-C
Examples of the cycloalkyl group 8 include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group. Examples of the C3-C6 alkenyl group include an allyl group, a 1-methyl-2-propenyl group, and a 3-butenyl group. , 2-butenyl group, 3-methyl-2-butenyl group, 2
-Methyl-3-butenyl group and the like;

Examples of the C1-C6 alkyl group represented by R ²⁶ and R ²⁷ include a methyl group, an ethyl group, a propyl group, and an isopropyl group. Examples of the C1-C6 haloalkyl group include a chloroethyl group and a bromoethyl group. And C3-C6 alkenyl groups include allyl group, 1
-Methyl-2-propenyl group, 3-butenyl group, 2-butenyl group, 3-methyl-2-butenyl group, 2-methyl-
3-butenyl group and the like, and the C3-C6 alkynyl group include a propargyl group, a 1-methyl-2-propynyl group, a 2-butynyl group and a 1,1-dimethyl-2-propynyl group. Examples of the C1-C6 alkyl group include a cyanomethyl group and a cyanoethyl group.
As the C1-C4 alkoxy C1-C4 alkyl group,
Examples of the methoxymethyl group, methoxyethyl group, ethoxymethyl group, ethoxyethyl group and the like, and examples of the C1-C4 alkylthio C1-C4 alkyl group include a methylthiomethyl group and a methylthioethyl group.
Examples of the 1-C6 alkyl group include a carboxymethyl group, 1
-Carboxyethyl group, 2-carboxyethyl group and the like, and (C1-C6 alkoxy) carbonyl C1-C
6 alkyl groups include a methoxycarbonylmethyl group,
Ethoxycarbonylmethyl group, propoxycarbonylmethyl group, isopropoxycarbonylmethyl group, butoxycarbonylmethyl group, isobutoxycarbonylmethyl group, t-butoxycarbonylmethyl group, amyloxycarbonylmethyl group, isoamyloxycarbonylmethyl group, t-amyloxy Carbonylmethyl group, 1-methoxycarbonylethyl group, 1-ethoxycarbonylethyl group, 1-propoxycarbonylethyl group, 1-isopropoxycarbonylethyl group, 1-butoxycarbonylethyl group, 1-isobutoxycarbonylethyl group, 1- t
-Butoxycarbonylethyl group, 1-amyloxycarbonylethyl group, 1-isoamyloxycarbonylethyl group, 1-t-butoxycarbonylethyl group, 1-amyloxycarbonylethyl group, 1-isoamyloxycarbonylethyl group, 1-t -Amyloxycarbonylethyl group and the like, and (C3-C8 cycloalkoxy)
Examples of the carbonyl C1-C6 alkyl group include a cyclobutyloxycarbonylmethyl group, a cyclopentyloxycarbonylmethyl group, a cyclohexyloxycarbonylmethyl group, a 1-cyclobutyloxycarbonylethyl group,
1-cyclopentyloxycarbonylethyl group, 1-cyclohexyloxycarbonylethyl group and the like,
The {(C1-C4 alkoxy) C1-C4 alkyl} carbonyl C1-C6 alkyl group, methoxy methoxycarbonylmethyl group, 1-methoxy-methoxycarbonylethyl group and the like, represented by R ²⁸ and R ²⁹ C1-
Examples of the C6 alkyl group include a methyl group, an ethyl group, a propyl group, and an isopropyl group. Examples of the C1-C6 haloalkyl group include a chloromethyl group, 2-chloroethyl, and a trifluoromethyl group. Examples of the phenyl group which may be substituted with a nitro group include a phenyl group, a 4-tolyl group, a 4-nitrophenyl group, and the like.

Examples of the C1-C6 alkyl group represented by R ^30, a methyl group, an ethyl group, a propyl group, an isopropyl group, an isobutyl group, butyl group, t- butyl group, amyl group, isoamyl group, t-amyl group and the like And C2-
Examples of the C6 alkenyl group include a vinyl group, an allyl group,
-Methylvinyl group, 2-methylvinyl group, 1-methyl-
2-propenyl group, 3-butenyl group, 2-butenyl group,
3-methyl-2-butenyl group, 2-methyl-3-butenyl group and the like, and as the C2-C6 alkynyl group,
An ethynyl group, a 2-methylethynyl group, a propargyl group,
1-methyl-2-propynyl group, 2-butynyl group, 1,
1-dimethyl-2-propynyl group and the like. Examples of the C1-C6 alkyl group represented by R ³¹ include a methyl group, an ethyl group, a propyl group, an isopropyl group, an isobutyl group,
Butyl group, t-butyl group, amyl group, isoamyl group, t
-Amyl group and the like. Examples of the C1-C6 haloalkyl group include a 2-chloroethyl group, a 2-bromoethyl group,
2,2,2-trifluoroethyl group and the like, and C3
Examples of the -C6 alkenyl group include an allyl group, a 1-methyl-2-propenyl group, a 3-butenyl group, a 2-butenyl group, a 3-methyl-2-butenyl group, and a 2-methyl-3-butenyl group. Examples of the C3-C6 haloalkenyl group include a 2-chloro-2-propenyl group and a 3,3-dichloro-2-propenyl group. Examples of the C3-C6 alkynyl group include a propargyl group and a 1-methyl -2
-Propynyl group, 2-butynyl group, 1,1-dimethyl-
2-propynyl group and the like, and the cyano C1-C6 alkyl group include a cyanomethyl group and the like.
Examples of the C4 alkoxy C1-C4 alkyl group include a methoxyethyl group and an ethoxyethyl group.
Examples of the 4-alkylthio C1-C4 alkyl group include a methylthioethyl group, and examples of the carboxy C1-C6 alkyl group include a carboxymethyl group, a 1-carboxyethyl group, and a 2-carboxyethyl group.
Examples of 1-C6 alkoxy) carbonyl C1-C6 alkyl groups include methoxycarbonylmethyl, ethoxycarbonylmethyl, propoxycarbonylmethyl, isopropoxycarbonylmethyl, butoxycarbonylmethyl, isobutoxycarbonylmethyl, and t-butoxycarbonyl. Methyl group, amyloxycarbonylmethyl group, isoamyloxycarbonylmethyl group, t-amyloxycarbonylmethyl group, 1-methoxycarbonylethyl group, 1-ethoxycarbonylethyl group, 1-propoxycarbonylethyl group, 1-isopropoxycarbonylethyl Group, 1-butoxycarbonylethyl group, 1-isobutoxycarbonylethyl group, 1-t-butoxycarbonylethyl group, 1-amyloxycarbonylethyl group, 1-isoamyl Butoxycarbonyl ethyl group, 1-t
-Butoxycarbonylethyl group, 1-amyloxycarbonylethyl group, 1-isoamyloxycarbonylethyl group, 1-t-amyloxycarbonylethyl group and the like, and (C3-C8 cycloalkoxy) carbonyl C
Examples of the 1-C6 alkyl group include a cyclobutyloxycarbonylmethyl group, a cyclopentyloxycarbonylmethyl group, a cyclohexyloxycarbonylmethyl group, a cyclobutyloxycarbonylethyl group, a cyclopentyloxycarbonylethyl group, a cyclohexyloxycarbonylethyl group, and the like. {(C1-C4 alkoxy) C1-C4 alkoxy} carbonyl C1-C6 alkyl groups include methoxymethoxycarbonylmethyl, methoxyethoxycarbonylmethyl, 1-methoxyethoxycarbonylethyl, and the like.

Among the compounds of the present invention, preferred from the viewpoint of herbicidal activity.
As a new substituent, R^TwoIs a hydrogen atom or C1
—C3 alkyl group, particularly, hydrogen atom or methyl.
And R is preferably^ThreeWas replaced by a fluorine atom
Methyl group (for example, trifluoromethyl group, chlorodifur
Oromethyl group, difluoromethyl group) and fluorine atom
A substituted ethyl group (for example, a pentafluoroethyl group)
And a trifluoromethyl group is particularly preferable.
Q-1, Q-2, Q-3 or Q-4
You. Preferred compounds from the viewpoint of herbicidal activity among the compounds of the present invention
Compounds that combine the above preferred substituents
Is raised. When Q is Q-1, X is water
A hydrogen atom or a fluorine atom, and Y is a chlorine atom
Compounds are more preferable, and among them, B is OR^TenGroup, SR^Ten
Group, N (R¹²) R¹³Group, NR¹²(SO_TwoR²⁸) Group or
COOR^{twenty two}Is more preferable, and further, R^TenBut
C1-C6 alkyl group, C3-C6 alkenyl group, C3
-C6 alkynyl group, (C1-C8 alkoxy) carbo
An aryl C1-C6 alkyl group or (C3-C8 cycloa
Alkoxy) carbonyl C1-C6 alkyl group, R¹²But water
Elemental atom, R¹³Is (C1-C6 alkoxy) carbonyl C
1-C6 alkyl group, R²⁸Is a C1-C6 alkyl group or
Is most preferably a compound which is a C1-C6 haloalkyl group.
No. When Q is Q-2, X is a hydrogen atom or fluorine.
Nitrogen atom and Z¹Is an oxygen atom and n is 1
Or X is a hydrogen atom or a fluorine atom and Z ¹
Is more preferably a compound wherein n is 0,
Further, R^FiveIs a C1-C6 alkyl group or C3-C6
Compounds that are alkynyl groups are most preferred.

The compound of the present invention may have an optical isomer or a diastereomer derived from an asymmetric carbon atom, and the compound of the present invention also includes all of these isomers and mixtures thereof.

Next, a method for producing the compound of the present invention will be described. (Production Method 1) Among the compounds of the present invention,

Embedded image [Wherein, R ^1, R ² and R ³ are as defined above, Q ¹
Is the general formula

Embedded image中 where X, Y, Z¹, Z^Two, N, R^Four, R^Five, R⁷And R⁸
Represents the same meaning as described above, and R^6-1Is C1-C6 alkyl
Group, C1-C6 haloalkyl group, hydroxy C1-C6
Alkyl group, C1-C6 alkoxy C1-C6 alkyl
A C1-C4 alkylthio C1-C4 alkyl group or
Is C1-C6 alkoxy C1-C6 alkoxy C1-C
6 represents an alkyl group;¹Is a hydrogen atom, a halogen atom,
Nitro group, OR^10-1Group, SR^10-1Group, N (R^{12- 1}) R
^13-1Group, NR^12-1(COR⁹) Group, NR^12-1(SO
_TwoR²⁸) Group, N (SO_TwoR ²⁸) (SO_TwoR²⁹) Group, N (S
O_TwoR²⁸) (COR⁹) Group, COOR³²Group, CON (R
^12-1) R^13-1Group, CSN (R^12-1) R^13-1Group, CR^{twenty three}=
CR^{twenty four}COOR^{twenty five}Group, CR^{twenty three}= CR^{twenty four}CON (R^12-1)
R^13-1Group, CH_TwoCHWCOOR^{twenty five}Group, CH_TwoCHWCO
N (R^12-1) R^13-1Group, CR³⁰= NOR³¹Group, CR³⁰=
NN (R^12-1) R^13-1Represents a group. (Where R⁹, R^{twenty three},
R^{twenty four}, R²⁸, R²⁹, R³⁰And R³¹Represents the same meaning as above.
Then R^12-1And R^13-1Is R¹²And R¹³Medium hydrogen atom
A substituent other than^10-1Is a hydrogen atom, C1-C6
Alkyl group, C1-C6 haloalkyl group, C3-C6 cycle
Loalkyl group, benzyl group, C3-C6 alkenyl group,
C3-C6 haloalkenyl group, C3-C6 alkynyl
Group, C3-C6 haloalkynyl group, cyano C1-C6
Alkyl group, C1-C4 alkoxy C1-C4 alkyl
A C1-C4 alkylthio C1-C4 alkyl group,
Ruboxy C1-C6 alkyl group, (C1-C8 alkoxy
B) a carbonyl C1-C6 alkyl group;
Loalkoxy) carbonyl C1-C6 alkyl group,
{(C1-C4 alkoxy) C1-C4 alkoxy}
Rubonyl C1-C6 alkyl group, (C3-C8 cycloa
Alkoxy) carbonyl C1-C6 alkyl group, CH_TwoC
ON (R^12-1) R^13-1Group, CH (C1-C4 alkyl)
CON (R^12-1) R^13-1Group (where R^12-1And R^13-1
Has the same meaning as described above. ), ｛(C1-C6 alkoxy)
B) carbonyl C1-C6 alkyl @ oxycarbonyl
A C1-C6 alkyl group or hydroxy C1-C6
Represents a alkyl group. Q indicated by｝¹-1, Q-2, Q¹−
3, represents either Q-4 or Q-5. ]
A method for producing a compound.

The compound of the present invention represented by the general formula (9)
General formula 11

Embedded image [Wherein Q ¹ , R ¹ and R ³ represent the same meaning as described above. And a hydrazone derivative of the general formula

Embedded image (C ₆ H ₅ ) ₃ P （C (R ² ) COOR ³³ wherein R ² has the same meaning as described above, and R ³³ is C1-C
6 represents an alkyl group. And a phosphorane compound represented by the following formula: The reaction is usually performed in a solvent, and the reaction temperature is usually in the range of -20.
１５０150 ° C., preferably 20-130 ° C.,
The range of reaction time is usually from instant to 72 hours. The amount of the reagent used in the reaction is a theoretical amount of 1 mol of the phosphorane compound to 1 mol of the hydrazone compound represented by the general formula (11), but may vary arbitrarily depending on the reaction conditions. it can. Examples of the solvent include aliphatic hydrocarbons such as hexane, heptane, nonane, decane, ligroin, cyclohexane, petroleum ether, aromatic hydrocarbons such as benzene, toluene, xylene, and mesitylene, monochlorobenzene, dichlorobenzene, and benzotrifluoride. Halogenated aromatic hydrocarbons such as, ethers such as diethyl ether, diisopropyl ether, 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, methyl-t-butyl ether; nitro compounds such as nitromethane and nitrobenzene; formamide; Acid amides such as N-dimethylformamide and acetamide, pyridine, triethylamine, diisopropylethylamine, tributylamine, N, N-dimethylaniline, N, N-diethylaniline , Tertiary amines such as N-methylmorpholine, sulfur compounds such as dimethyl sulfoxide and sulfolane, methanol, ethanol, propanol, isopropanol, butanol, t
-Alcohols such as butanol, amyl alcohol, isoamyl alcohol, and t-amyl alcohol; water; and mixtures thereof. After completion of the reaction, the reaction solvent is distilled off, and then the residue is subjected to chromatography, or the reaction solution is poured into water and subjected to ordinary post-treatment operations such as extraction with an organic solvent and concentration, if necessary. The target compound of the present invention can be isolated by performing operations such as chromatography and recrystallization.

(Production method 2) The compound of the present invention is produced by converting the compound produced by the method described in the above (Production method 1) into a substituent on the benzene ring according to a known method. You can also. As the conversion method, for example, a method described in JP-A-9-323977 can be used.

Next, a method for producing a starting compound for producing the compound of the present invention by (Production method 1) will be described. As the phosphorane compound represented by the general formula (12), a commercially available product is used, or for example, Experimental Chemistry Course (Maruzen Co., Ltd.)
It can be produced according to the method described in Vol. 24, 4th edition, pp. 259-260.

The hydrazone compound represented by the general formula 11 is represented by the general formula Q ¹ -NH ₂ wherein Q ¹ has the same meaning as described above. Is converted to a diazonium salt, and then the diazonium salt and the general formula R ³ C (＝ O) CH ₂ C (＝ O) COOR ¹ [wherein R ¹ and R ³ have the same meanings as described above. Represent. ] With an acetoacetic ester derivative represented by the following formula: The reaction is described, for example, in JP-A-9-32.
The method can be carried out according to the method described in JP-A-3977.

The compound of the present invention has an excellent herbicidal effect,
Some show excellent selectivity between crops and weeds. That is, the compound of the present invention has a herbicidal effect on various weeds which are the following problems in foliage treatment and soil treatment in the field. Polygonum weed: Polygonum con
volvulus), Polygonum (Polygonum)
lapathifolium), Polygonum pensylvanicu
m), Hartade (Polygonum persica)
ria), Rumex crisp
s), Rumex obtusifo (Rumex obtusifo)
lius) and knotweed (Polygonum csp)
idatum) Purslanaceae Weed: Purslane (Portulaca)
oleracea) Weeds: Stellaria med
ia) Chenopodium weed: Shiroza (Chenopodium al
bum), Butterfly (Kochia scopari)
a), Amaranthus weed: Amaranthus r.
etroflexus)
lanthus hybridus Brassicaceae Weed: Wild Radish (Raphan)
us raphanistrum)
inapis arvensis, Capsicum (Caps)
ella bursa-pastoris Legume weed: American hornbrush (Sesbania)
exaltata), Ebisugusa (Cassia ob)
tusifolia), Florida Vega Weed (De)
smodium tortuosum, white clover (Trifolum repens) Malvaceae weed: Abutilon theop
hrusti), American deer (Sida sp.)
inosa) Violet weeds: Field panji (Viola ar)
vensis), Wild Panji- (Viola tr)
icor) Rubiaceae Weed: Gallium apari
ne) Convolvulaceae weed: American morning glory (Ipomoea)
hederacea), Malva Asagao (Ipomoe)
a purpura), Malva American morning glory (I
pomoea hederacea var integ
riuscula) and bean sagao (Ipomoea)
lacunosa), Convolvulus convolvulus (Convol)
vulus arvensis Lamiaceae Weeds: Lameur pur
puree), Photohenosa (Lamium ampl)
exicaule) Solanaceae weeds: Datura japonicus (Data)
a stramonium) and dogwood (Sola)
num nigrum Scrophulariaceae Weed: Veronica
ca persica), scorpion (Veroni)
ca hederaefolia Asteraceae Weed: Xanthium pensy
lvanicum), wild sunflower (Helianth)
us annuus), dog chamomile (Matrica)
ria performata or inodora),
Common Gold (Chrysanthemum)
segetum), oro-shag (Matricari)
a matricarioides), Ragweed (Am)
brosia artemisiifolia, oobtaxa (Ambrosia trifidida), and swordweed (Erigeron canadensi)
s), mugwort (Artemisia print)
s), Solidago alga (Solidago al)
tissima) Purple weed: Forget-me-not (Myosotis a)
Ravensis (Coleoptera: Chrysomelidae): Asclepias
syriaca spurges weed: Euphorbi
a helioscopia), Onishikisou (Eu)
phorbia maculata Grass weed: Echinochloa cr
us-galli), Enokorogosa (Setaria)
viridis), Aquinoe nokorogosa (Setari)
a faberi), Meishishiba (Digitalias)
anguinalis), Hawkgrass (Eleusine)
indica), Poa annua (Poa annu)
a), Blackgrass (Alopecurus myo)
suloides), oats (Avena fat)
ua), Sorghum sorghum (Sorghum hale)
pense), barley (Agropyron rep)
ens), Umanohashiki (Bromus tecto)
rum), Cynodone dact (Cynodone dact)
ylon), cane millet (Panicum dich)
otomiflorum), Texas honeycomb (Pan)
icum texanum), Shata cane (Sor
ghum vulgare Cyperaceae Weed: Commelina co
mmunis) Rhododendron weeds: horsetail (Equisetum arve)
nse) Cyperaceae Weeds: Cygous cyperus (Cyperus)
iria), nectarine (Cyperus rotund)
us), yellowtail sedge (Cyperus esculen)
tus)

Some of the compounds of the present invention include corn (Zea mays) and wheat (Tritic).
um aestivum), barley (Hordeum)
vulgare), rice (Orysa sativ)
a), sorghum (Sorghum bicolor),
Soybean (Glycine max), Cotton (Gossy
pium spp. ), Sugar beet (Beta vulga)
ris), peanuts (Arachis hypoga)
ea), sunflower (Helianthus annuu)
s), and does not show any phytotoxicity that would be a problem for main crops such as rapeseed (Brassica napus) and horticultural crops such as flowers and vegetables. Further, the compound of the present invention, soybean,
Various weeds that are problematic in non-tillage cultivation of corn, wheat, etc. can be effectively eliminated. Moreover, some of the compounds of the present invention do not exhibit any harmful effects on crops.

The compound of the present invention has a herbicidal effect on various weeds, which are the following problems in flooding treatment of paddy fields. Grass weeds: Echinochloa o
ryzicola) Scrophulariaceae Weed: Azena (Lindernia p.
rocumbens) Loxodontaceae Weeds: Rota indi
ca), hamemisohagi (Ammannaia multi)
flora) Dipterocarpaceae Weeds: Dictyostelium (Elatine tr)
iandra) Cyperaceae Weeds: Cyperus
diffirmis), fireflies (Sirpus j)
uncoides, pine trees (Eleocharis)
Acicularis) and Cyperus (Cyper)
us serotinus, Krogwai (Eleoc)
haris kuroguwai Watermelonaceae Weed: Monochoria v
aginalis) Weeds: Urikawa (Sagittaria p.
ygmaea), Omodaka (Sagittariat)
rifolia), Spiderfish (Alismacan)
aliculatum Weevil: Weevil (Potamogeto)
N distinctus Apiaceae Weeds: Api (Oenanthe Javanic)
a) Moreover, some of the compounds of the present invention do not show any phytotoxicity that would cause a problem for transplanted rice.

In addition, the compounds of the present invention can control a wide range of weeds in orchards, pastures, lawns, forestry or waterways, canals or other non-crop land. In addition, the compound of the present invention can be used in water hyacinth (E
It has herbicidal activity against aquatic weeds such as ichornia crassipes.

The compound of the present invention has the same properties as the herbicidal compound described in International Patent Application Publication No. WO95 / 34659, and is introduced with the herbicide resistance gene and the like described in the specification. In the case of cultivating crops to which tolerance has been imparted by the fact, it becomes possible to use the compound of the present invention in a larger dose than that used when cultivating normal crops to which tolerance has not been imparted. Can be weeded more effectively.

When the compound of the present invention is used as an active ingredient of a herbicide, a solid carrier, a liquid carrier, a surfactant,
It is mixed with other formulation auxiliaries to form emulsions, wettable powders, suspensions, granules, concentrated emulsions, wettable granules and the like.
These preparations contain the compound of the present invention as an active ingredient in a weight ratio of 0.001 to 80%, preferably 0.005 to 7%.
It contains 0%. As solid carriers, kaolin clay, attapulgite clay, bentonite, acid clay, pyrophyllite, talc, diatomaceous earth, mineral fine powder such as calcite, organic fine powder such as walnut shell powder, water-soluble organic fine powder such as urea Fine powders of inorganic salts such as ammonium sulfate and ammonium sulfate, and fine powders of synthetic hydrous silicon oxide. As liquid carriers, aromatic hydrocarbons such as alkylbenzene such as methylnaphthalene, phenylxylylethane and xylene, isopropanol, ethylene Alcohols such as glycol and 2-ethoxyethanol, esters such as dialkyl phthalate, ketones such as acetone, cyclohexanone and isophorone, mineral oils such as machine oil, vegetable oils such as soybean oil and cottonseed oil. , Dimethyl sulfoxide, N, N-dimethylformamide, acetonitrile, N Methylpyrrolidone,
Water and the like. Surfactants used for emulsification, dispersion, wet spreading and the like include alkyl sulfates, alkyl sulfonates, alkyl aryl sulfonates,
Anionic surfactants such as dialkyl sulfosuccinate, polyoxyethylene alkyl aryl ether phosphate salt, polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene polyoxypropylene block Examples include nonionic surfactants such as copolymers, sorbitan fatty acid esters, and polyoxyethylene sorbitan fatty acid esters. Other auxiliaries for preparations include lignin sulfonate, alginate, polyvinyl alcohol, gum arabic, CMC (carboxymethyl cellulose), PAP
(Acidic isopropyl phosphate) and the like.

The compound of the present invention is usually formulated and subjected to soil treatment, foliage treatment or flooding treatment before or after emergence of weeds. Soil treatment includes soil surface treatment, soil admixture treatment, etc.For foliage treatment, in addition to treatment from above the plant,
There is a local treatment for treating only weeds so as not to adhere to crops.

When used in a mixture with other herbicides, the herbicidal effect may be enhanced. further,
It can also be used as a mixture with insecticides, acaricides, nematicides, fungicides, plant growth regulators, fertilizers, soil conditioners and the like.
Examples of herbicides that can be used in combination with the compound of the present invention are shown below. Atrazine, cyanazine, dimethamethrin (di
methamryn), metribuzin (metri)
buzin), promethrin (prometryn),
Simazine, Simetrine (sime)
trin), chlorotoluron
on), diuron, dimuron (dy)
mrone), fluometuron (fluometro)
n), isoproturon,
Linuron, metabenzthiazuron, bromoxynil, ioxynil (i
oxynil), ethalfluralin (ethalflu)
ralin), pendimethalin (pendimeth)
alin), trifluralin
n), acifluorfen
n), acifluorfen Na salt (acifluorf)
en-sodium), bifenox (bifeno)
x), chloromethoxynil
l), fomesafen (fomesafen), lactofen (lactofen), oxadiazon (oxa)
diazon), oxadiargyl (oxadiarg)
yl), oxyfluorfen
n), carfentrazone-ethyl (carfentra)
zone-ethyl), full micro rack pentyl (f
lumicolac-pentyl), flumioxazine, fluthiacet-methyl, sulfentrazone, thidiazimin, azafenidin, azafenidin ethyl, pyraflufenidin
iraflufen-ethyl, difenzoquat, diquat
t), paraquat, 2,4-D,
2,4-DB, DCPA, MCPA, MCPB, Clomeprop, Clopyralide (cl)
opylid), dicamba, dithiopyr, fluroxypyr (f)
luroxypyr), mecoprop
p), naproanilide,
Phenothiol, quinclorac, triclopyr (tri)
clopyr), thiazopyr,
Acetochlor, arachlor
(Alachlor), butachlor (butach)
lor), diethathyl-ethyl
thyl), metolachlor
r), pretilachlor (pretilachlor)
r), propachlor, bensulfuron-methyl
yl), chlorsulfuron
n), chlorimuron-ethyl
ethyl, halosulfuron-methyl (halosul)
furon-methyl), Metsulfuron methyl (m
etsulfuron-methyl, nicosulfuron, primisulfuron-methyl,
Pyrazosulfuron ethyl
n-ethyl), sulfometuron methyl (sulf)
omethuron-methyl, thifensulfuron-methyl
l), triasulfuron
n), tribenuron-methyl (tribenuron-
methyl, oxasulfuron (oxasulfu)
ron), azimsulfuron
n), cloranslam methyl
-Methyl), cyclosulfamuron (cyclo)
Sulfamuron), Flumeturam (flumet)
sulam), flupyrisulfuron (flupyrsu)
lfuron), flazasulfuron
furon), imazosulfuron (imazosulf)
uron), metoslam, dicloslam, prosulfuron, rimsulfuron (rim)
sulfuron), trifluorosulfuron-methyl (tr
iflusulfuron-methyl, ethoxysulfuron, sulfosulfuron, imazamethabenz-me
thyl), imazapyr, imazaquin, imazethapyr
ethapyr), imazameth (imazamet)
h), imazamox, bispyribac-Na salt (bispyribac-sodiu)
m), pyriminobac methyl
-Methyl), pyrithiobac Na salt (pyrit)
hibac-sodium, alloxydim-sodium, clethodim, clethoxydim, setoxydim (setoxim)
ydim), tralkoxydim (tralkoxydi)
m), dichlohop-methyl
thyl), fenoxaprop-ethyl (fenoxa)
prop-ethyl), phenoxalop-p-ethyl, fluazifop-butyl,
Fluazifop-p-butyl
-Butyl), haloxyfop-methyl (haloxy)
fop-methyl), quizalofop-p-ethyl, quihalofop-butyl, clodinafop-propargyl (clodinafop-p)
ropargyl), benzofenap (benzof)
enap), clomazone, diflufenican, norflurazon, pyrazolate (p
yrazolate), pyrazoxifen (pyraz)
oxyfen), flurtamon
e), isoxaflutol (isoxaflutol)
e), sulcotrione, glufosinate ammonium salt (glufosinat)
e-ammonium), glyphosate (glyph)
osate), bentazone, bentiocarb, bromobutide, butamifos (butam)
ifos), butyrate, butyrate, dimepiperate, dimethenamide, DSMA, EPT
C, esprocarb, isoxaben, mefenacet (mefe)
nailet), molinate, MS
MA, piperophos, pyributicarb, propanil, pyridat
e), trilate, cafenstrol, flupoxam, fluthiamide
mide), diflufenzopyr (diflufenz)
opyr), triazifuram
m), pentoxazone, epoprodan, metobenzuron, oxaziclomefone Oxaziclomefone The above compounds were obtained from the Farm Chemicals Handbook (Meister Pudding Company).
blishing Company)] Catalog of 1995 edition, Agchem New Compound Review 1995 edition (Agchem Information Service) [AG CHEM NEW COMPOUND R
EVIEW, VOL. 13, 1995 (AG CHEM INFORMATION SERVICE), Agchem New Compound Review 1997 Edition (Agchem Information Service) [AG CHEM NEW COMP
OUND REVIEW, VOL.15,1997 (AG CHEM INFORMATION SERVIC
E), Herbicide Research Directory (Hakutosha) or Herbicide Handbook, 7th Edition (published by the American Weed Society) (HERBICID
E HANDBOOK-Seven Edition (Weed Science Society of A
merica)).

When the compound of the present invention is used as an active ingredient of a herbicide, the amount of treatment varies depending on weather conditions, preparation form, treatment time, treatment method, soil conditions, target crops and target weeds. Usually 0.1g-500 per
00 g, preferably 1 g to 10000 g, and an emulsion,
Wettable powders, suspensions, concentrated emulsions, wettable powders, etc.
Usually, the predetermined amount is 10 liters to 1 liter per hectare.
It is diluted and treated with 000 liters of water (added with auxiliary agents such as a spreading agent if necessary), and granules and certain suspending agents are usually treated without any dilution. Here, as an auxiliary agent used if necessary, in addition to the above-mentioned surfactant, polyoxyethylene resin acid (ester), lignin sulfonate, abietic acid salt, dinaphthylmethane disulfonate, crop oil concentrate ( c
and vegetable oils such as soybean oil, corn oil, cottonseed oil, sunflower oil and the like.

The compound of the present invention can be used as a cotton defoliant / desiccant, potato (Solanum tuberosum).
Can be used as an active ingredient of a harvesting aid such as a desiccant. In this case, the compound of the present invention is usually formulated in the same manner as when used as an active ingredient of a herbicide, and is foliage-treated alone or in combination with other harvesting aids before harvesting the crop.

[0036]

EXAMPLES The present invention will be described in more detail with reference to Production Examples, Preparation Examples and Test Examples, but the present invention is not limited to these Examples. First, Production Examples of the compound of the present invention will be shown. The starting compounds are indicated by the compound numbers in Table 1 below. Production Example 1 3.22 g of (Compound 1-16) and (carbethoxymethylene) triphenylphosphorane ((C ₆ H ₅ ) ₃ P = CHC
OOC ₂ H ₅ ) (4.18 g) was dissolved in toluene (50 ml), and the mixture was heated under reflux for 6.5 hours. After distilling off the solvent under reduced pressure,
The residue was subjected to silica gel column chromatography (developing solvent: hexane / ethyl acetate = 4/1), and the obtained crystals were washed with hexane to give 2- (4-chlorophenyl) -6-ethoxycarbonyl-5-trifluoromethylpyridazine. 1.27 g of -3-one (37% yield) was obtained. ¹ H-NMR (CDCl ₃ /250MHz);1.40
(3H, t), 4.44 (2H, q), 7.41 (1
H, s), 7.47 (2H, d), 7.63 (2H,
d)

Production Example 2 3.99 g of (Compound 1-4) and (carbethoxyethylidene) triphenylphosphorane ((C ₆ H ₅ ) ₃ P = C (C
3.99 g of H ₃ ) COOC ₂ H ₅ ) in 50 ml of toluene
And heated under reflux for 10 hours. After evaporating the solvent under reduced pressure, silica gel column chromatography (developing solvent:
Hexane / ethyl acetate = 9/1) to give 2- (4-chloro-2-fluoro-5-isopropoxyphenyl)-
2.63 g of 6-ethoxycarbonyl-4-methyl-5-trifluoromethylpyridazin-3-one (yield 60
%). ¹ H-NMR (CDCl ₃ /250MHz);1.35-
1.41 (9H, m), 2.48 (3H, q), 4.3
5-4.55 (3H, m), 6.98 (1H, d),
7.29 (1H, d)

Production Example 3 At room temperature, 2- (4-chloro-2-fluoro-5-isopropoxyphenyl) -6-ethoxycarbonyl-4-
1.0 g of methyl-5-trifluoromethylpyridazin-3-one and 1.0 g of sulfuric acid were mixed and stirred for 30 minutes. The reaction solution was poured into water and extracted with 100 ml of ethyl acetate. The organic layer was washed three times with 50 ml of water, dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the obtained crystals were washed with 50 ml of n-hexane to give 2- (4-chloro-2- Fluoro-5-hydroxyphenyl) -6
0.78 g (87% yield) of ethoxycarbonyl-4-methyl-5-trifluoromethylpyridazin-3-one was obtained. ¹ H-NMR (CDCl ₃ /300MHz);1.38
(3H, t), 2.49 (3H, q), 4.41 (2
H, q), 5.72 (1H, br), 7.08 (1H,
d), 7.25 (1H, d)

Production Example 4 12.5 g of (Compound 1-18) and (carbethoxyethylidene) triphenylphosphorane ((C ₆ H ₅ ) ₃ P = C
(CH ₃ ) COOC ₂ H ₅ ) 12.19 g and toluene 1
Then, the mixture was heated to reflux for 5 hours. Thereafter, the solvent was distilled off under reduced pressure, and the residue was subjected to silica gel column chromatography (developing solvent: hexane / ethyl acetate = 9/1).
To give 2- (4-chloro-3-isopropoxycarbonylphenyl) -6-ethoxycarbonyl-4-methyl-5-trifluoromethylpyridazin-3-one 7.5.
5 g (55% yield) were obtained. ¹ H-NMR (CDCl ₃ /300MHz);1.35-
1.43 (9H, m), 2.48 (3H, q), 4.4
6. 2 (2H, q) 5.20-5.35 (1H, m), 7.
55 (1H, d), 7.69 (1H, dd), 8.08
(1H, d)

Next, a method for producing the starting compound of the compound of the present invention will be described as a reference example. Reference Example 1 A mixture of 6.38 g of 4-chloroaniline and 30 ml of concentrated hydrochloric acid (35 to 37% by weight) was heated at 50 ° C. for 55 minutes. The solution was cooled to 0 ° C., and a solution of 3.62 g of sodium nitrite dissolved in 10 ml of water was added dropwise at 0 ° C., followed by stirring at the same temperature for 2 hours to prepare a diazonium salt solution. In another flask, 35 g of sodium acetate and 50 g of water
8. ml, ethyl 3,3,3-trifluoroacetoacetate
66 g were mixed and cooled to 0 ° C. The above diazonium salt solution was added dropwise to this solution at 0 ° C. over 15 minutes. After the reaction solution was heated to room temperature and stirred for 55 minutes, the generated crystals were collected by filtration, washed with water, and dried under reduced pressure at a temperature of 50 ° C. to obtain 15.23 g of (Compound 1-16). Obtained. 95% yield.

Reference Example 2 10.69 g of isopropyl 5-amino-2-chlorobenzoate was added to 60 ml of concentrated hydrochloric acid (35 to 37% by weight) cooled to 0 ° C. This was heated to room temperature, stirred for 30 minutes, and then cooled again to 0 ° C. To this solution, a solution of 3.62 g of sodium nitrite dissolved in 20 ml of water was added dropwise at 0 ° C. over 5 minutes, and the mixture was further stirred at 0 ° C. for 30 minutes to prepare a diazonium salt solution. In another flask, 70.0 g of sodium acetate, 100 ml of water, and 9.21 g of ethyl 3,3,3-trifluoroacetoacetate were mixed and cooled to 0 ° C. The above diazonium salt solution was added dropwise to this solution at 0 ° C. over 10 minutes, and the reaction solution was further added to 0%.
After stirring at 1 ° C. for 1 hour, the reaction solution was poured into water and extracted with 500 ml of ethyl acetate. The organic layer was washed twice with 500 ml of water, dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the residue was subjected to silica gel column chromatography (hexane: ethyl acetate = 9: 1-3: 1). ,
13.13 g (64% yield) of (Compound 1-18) were obtained as crystals. ¹ H-NMR (CDCl ₃ /300MHz);1.40-
1.45 (9H, m), 4.42 (2H, q), 5.2
9 (1H, m), 7.45-7.55 (2H, m),
7.83 (1H, d)

Some examples of the compound of the present invention are shown below. (1) Formula 13

Embedded image Wherein Ar is 4-fluorophenyl
Group, 4-chlorophenyl group, 4-bromophenyl group,
3-nitro-4-fluorophenyl group, 3-nitro-4
-Chlorophenyl group, 3-nitro-4-bromophenyl
Group, 3-amino-4-fluorophenyl group, 3-amino
-4-chlorophenyl group, 3-amino-4-bromophene
Nyl group, 3-hydroxy-4-fluorophenyl group, 3
-Hydroxy-4-chlorophenyl group, 3-hydroxy
-4-bromophenyl group, 3-mercapto-4-fluoro
Rophenyl group, 3-mercapto-4-chlorophenyl
Group, 3-mercapto-4-bromophenyl group, 3-chloro
Losulfonyl-4-fluorophenyl group, 3-chloros
Rufonyl-4-chlorophenyl group, 3-chlorosulfoni
4-bromophenyl group, 3-methylamino-4-f
Fluorophenyl group, 3-methylamino-4-chlorophene
Nyl group, 3-methylamino-4-bromophenyl group, 3
-Ethylamino-4-fluorophenyl group, 3-ethyl
Amino-4-chlorophenyl group, 3-ethylamino-4
-Bromophenyl group, 3-allylamino-4-fluoro
Phenyl group, 3-allylamino-4-chlorophenyl
Group, 3-allylamino-4-bromophenyl group, 3-p
Lopargylamino-4-fluorophenyl group, 3-pro
Pargylamino-4-chlorophenyl group, 3-propal
Gilamino-4-bromophenyl group, 3- (1-methyl
-2-propynylamino) -4-fluorophenyl group,
3- (1-methyl-2-propynylamino) -4-chloro
Rophenyl group, 3- (1-methyl-2-propynylamido)
No) 4-bromophenyl group, 3-methanesulfonylua
Mino-4-fluorophenyl group, 3-methanesulfonyl
Amino-4-chlorophenyl group, 3-methanesulfonyl
Amino-4-bromophenyl group, 3-ethanesulfonyl
Amino-4-fluorophenyl group, 3-ethanesulfoni
Ruamino-4-chlorophenyl group, 3-ethanesulfoni
Ruamino-4-bromophenyl group, 3-chloromethanes
Ruphonylamino-4-fluorophenyl group, 3-chloro
Methanesulfonylamino-4-chlorophenyl group, 3-
Chloromethanesulfonylamino-4-bromophenyl
Group, 3-trifluoromethanesulfonylamino-4-f
Fluorophenyl group, 3-trifluoromethanesulfonyl
Amino-4-chlorophenyl group, 3-trifluorometa
Sulfonylamino-4-bromophenyl group, 3- (di
A methanesulfonylamino) -4-fluorophenyl group,
3- (dimethanesulfonylamino) -4-chlorophenyl
Group, 3- (dimethanesulfonylamino) -4-bromo
Phenyl group, 3- (methanesulfonyl (methyl) amido
(No) -4-fluorophenyl group, 3- (methanesulfoni
(Methyl) amino) -4-chlorophenyl group, 3-
(Methanesulfonyl (methyl) amino) -4-bromofur
Phenyl, 3- (methanesulfonyl (propargyl) a
Mino) -4-fluorophenyl group, 3- (methanesulfo
Nyl (propargyl) amino) -4-chlorophenyl
Group, 3- (methanesulfonyl (propargyl) amino)
-4-bromophenyl group, 3-methoxycarbonylamido
No-4-fluorophenyl group, 3-methoxycarbonyl
Amino-4-chlorophenyl group, 3-methoxycarbonyl
Lumin-4-bromophenyl group, 3-ethoxycarbo
Nilamino-4-fluorophenyl group, 3-ethoxyca
Rubonylamino-4-chlorophenyl group, 3-ethoxy
Carbonylamino-4-bromophenyl group, 3-propo
Xycarbonylamino-4-fluorophenyl group, 3-
A propoxycarbonylamino-4-chlorophenyl group,
3-propoxycarbonylamino-4-bromophenyl
Group, 3-isopropoxycarbonylamino-4-fluoro
Rophenyl group, 3-isopropoxycarbonylamino-
4-chlorophenyl group, 3-isopropoxycarbonyl
Amino-4-bromophenyl group, 3-butoxycarboni
Ruamino-4-fluorophenyl group, 3-butoxycal
Bonylamino-4-chlorophenyl group, 3-butoxyca
Rubonylamino-4-bromophenyl group, 3-amylio
Xycarbonylamino-4-fluorophenyl group, 3-
Amyloxycarbonylamino-4-chlorophenyl
Group, 3-amyloxycarbonylamino-4-bromop
Enyl group, 3-methoxycarbonylmethylamino-4-
Fluorophenyl group, 3-methoxycarbonylmethyla
Mino-4-chlorophenyl group, 3-methoxycarbonyl
Methylamino-4-bromophenyl group, 3-ethoxyca
Rubonylmethylamino-4-fluorophenyl group, 3-
Ethoxycarbonylmethylamino-4-chlorophenyl
Group, 3-ethoxycarbonylmethylamino-4-bromo
Phenyl group, 3-propoxycarbonylmethylamino-
4-fluorophenyl group, 3-propoxycarbonyl
Tylamino-4-chlorophenyl group, 3-propoxyca
Rubonylmethylamino-4-bromophenyl group, 3-bu
Toxylcarbonylmethylamino-4-fluorophenyl
Group, 3-butoxycarbonylmethylamino-4-chloro
Phenyl group, 3-butoxycarbonylmethylamino-4
-Bromophenyl group, 3-amyloxycarbonylmethyl
Ruamino-4-fluorophenyl group, 3-amyloxy
Carbonylmethylamino-4-chlorophenyl group, 3-
Amyloxycarbonylmethylamino-4-bromofe
Nyl group, 3-isopropoxycarbonylmethylamino-
4-fluorophenyl group, 3-isopropoxycarboni
Methylamino-4-chlorophenyl group, 3-isopro
Poxycarbonylmethylamino-4-bromophenyl
Group, 3-cyclopentyloxycarbonylmethylamino
-4-fluorophenyl group, 3-cyclopentyloxy
Carbonylmethylamino-4-chlorophenyl group, 3-
Cyclopentyloxycarbonylmethylamino-4-bu
Lomophenyl group, 3-cyclohexyloxycarbonyl
Methylamino-4-fluorophenyl group, 3-cyclo
Xyloxycarbonylmethylamino-4-chlorophen
Nyl group, 3-cyclohexyloxycarbonylmethyla
Mino-4-bromophenyl group, 3-((1-methoxyca
Rubonylethyl) amino) -4-fluorophenyl group,
3-((1-methoxycarbonylethyl) amino) -4
-Chlorophenyl group, 3-((1-methoxycarbonyl
Ethyl) amino) -4-bromophenyl group, 3-((1
-Ethoxycarbonylethyl) amino) -4-fluoro
Phenyl group, 3-((1-ethoxycarbonylethyl)
Amino) -4-chlorophenyl group, 3-((1-ethoxy)
Cicarbonylethyl) amino) -4-bromophenyl
Group, 3-((1-propoxycarbonylethyl) amido
No) 4-fluorophenyl group, 3-((1-propoxy)
Cicarbonylethyl) amino) -4-chlorophenyl
Group, 3-((1-propoxycarbonylethyl) amido
No) 4-bromophenyl group, 3-((1-butoxyca)
Rubonylethyl) amino) -4-fluorophenyl group,
3-((1-butoxycarbonylethyl) amino) -4
-Chlorophenyl group, 3-((1-butoxycarbonyl
Ethyl) amino) -4-bromophenyl group, 3-((1
-Amyloxycarbonylethyl) amino) -4-fur
Orophenyl group, 3-((1-amyloxycarbonyl
Ethyl) amino) -4-chlorophenyl group, 3-((1
-Amyloxycarbonylethyl) amino) -4-bro
Mophenyl group, 3-((1-isopropoxycarbonyl
Ethyl) amino) -4-fluorophenyl group, 3-
((1-isopropoxycarbonylethyl) amino)-
4-chlorophenyl group, 3-((1-isopropoxy
Rubonylethyl) amino) -4-bromophenyl group, 3
-((1-cyclopentyloxycarbonylethyl) a
Mino) -4-fluorophenyl group, 3-((1-cyclo
Pentyloxycarbonylethyl) amino) -4-chloro
Rophenyl group, 3-((1-cyclopentyloxycal
Bonylethyl) amino) -4-bromophenyl group, 3-
((1-cyclohexyloxycarbonylethyl) amido
No) 4-fluorophenyl group, 3-((1-cyclo
Xyloxycarbonylethyl) amino) -4-chloro
Phenyl group, 3-((1-cyclohexyloxycarbo
Nylethyl) amino) -4-bromophenyl group,
Toxic-4-fluorophenyl group, 3-methoxy-4-
Chlorophenyl group, 3-methoxy-4-bromophenyl
Group, 3-ethoxy-4-fluorophenyl group, 3-ethoxy
Xy-4-chlorophenyl group, 3-ethoxy-4-bro
Mophenyl group, 3-isopropoxy-4-fluorophene
Nil group, 3-isopropoxy-4-chlorophenyl group,
3-isopropoxy-4-bromophenyl group, 3-pro
Poxy-4-fluorophenyl group, 3-propoxy-4
-Chlorophenyl group, 3-propoxy-4-bromofe
Nyl group, 3- (2-chloroethoxy) -4-fluorophenyl
Enyl group, 3- (2-chloroethoxy) -4-chlorophenyl
Enyl group, 3- (2-chloroethoxy) -4-bromophenyl
Enyl group, 3- (1,1,2,2-tetrafluoroeth
Xy) -4-fluorophenyl group, 3- (1,1,2,2
2-tetrafluoroethoxy) -4-chlorophenyl
Group, 3- (1,1,2,2-tetrafluoroethoxy)
-4-bromophenyl group, 3-cyclopentyloxy-
4-fluorophenyl group, 3-cyclopentyloxy-
4-chlorophenyl group, 3-cyclopentyloxy-4
-Bromophenyl group, 3-cyclohexyloxy-4-
Fluorophenyl group, 3-cyclohexyloxy-4-
Chlorophenyl group, 3-cyclohexyloxy-4-bu
Lomophenyl group, 3-allyloxy-4-fluorophene
Nyl group, 3-allyloxy-4-chlorophenyl group, 3
-Allyloxy-4-bromophenyl group, 3- (2-k
(Rolo-2-propenyloxy) -4-fluorophenyl
Group 3- (2-chloro-2-propenyloxy) -4-
Chlorophenyl group, 3- (2-chloro-2-propenyl)
Oxy) -4-bromophenyl group, 3- (2,3-dic
(Rolo-2-propenyloxy) -4-fluorophenyl
Group, 3- (2,3-dichloro-2-propenyloxy)
-4-chlorophenyl group, 3- (2,3-dichloro-2)
-Propenyloxy) -4-bromophenyl group, 3-
(2-methyl-2-propenyloxy) -4-fluoro
Phenyl group, 3- (2-methyl-2-propenyloxy)
B) -4-chlorophenyl group, 3- (2-methyl-2-
Propenyloxy) -4-bromophenyl group, 3- (1
-Methyl-2-propenyloxy) -4-fluorophene
Nyl group, 3- (1-methyl-2-propenyloxy)-
4-chlorophenyl group, 3- (1-methyl-2-prope
Nyloxy) -4-bromophenyl group, 3-propargy
Luoxy-4-fluorophenyl group, 3-propargyl
Oxy-4-chlorophenyl group, 3-propargyloxy
4-bromophenyl group, 3- (1-methyl-2-propyl)
Lopinyloxy) -4-fluorophenyl group, 3- (1
-Methyl-2-propynyloxy) -4-chlorophenyl
Group, 3- (1-methyl-2-propynyloxy) -4
-Bromophenyl group, 3- (3-bromo-2-propini)
Ruoxy) -4-fluorophenyl group, 3- (3-bro
Mo-2-propynyloxy) -4-chlorophenyl group,
3- (3-bromo-2-propynyloxy) -4-bro
Mophenyl group, 3- (3-chloro-2-propynyloxy)
B) -4-fluorophenyl group, 3- (3-chloro-2)
-Propynyloxy) -4-chlorophenyl group, 3-
(3-chloro-2-propynyloxy) -4-bromofu
Enyl group, 3-cyanomethyloxy-4-fluorophene
Nyl group, 3-cyanomethyloxy-4-chlorophenyl
Group, 3-cyanomethyloxy-4-bromophenyl group,
3-methoxymethoxy-4-fluorophenyl group, 3-
Methoxymethoxy-4-chlorophenyl group, 3-methoxy
Cimethoxy-4-bromophenyl group, 3-ethoxymeth
Xy-4-fluorophenyl group, 3-ethoxymethoxy
-4-chlorophenyl group, 3-ethoxymethoxy-4-
Bromophenyl group, 3-methylthiomethyloxy-4-
Fluorophenyl group, 3-methylthiomethyloxy-4
-Chlorophenyl group, 3-methylthiomethyloxy-4
-Bromophenyl group, 3-carboxymethoxy-4-f
Fluorophenyl group, 3-carboxymethoxy-4-chloro
Rophenyl group, 3-carboxymethoxy-4-bromop
Enyl group, 3-methoxycarbonylmethoxy-4-fur
Orophenyl group, 3-methoxycarbonylmethoxy-4
-Chlorophenyl group, 3-methoxycarbonylmethoxy
-4-bromophenyl group, 3-ethoxycarbonyl meth
Xy-4-fluorophenyl group, 3-ethoxycarboni
Methoxy-4-chlorophenyl group, 3-ethoxycal
Bonylmethoxy-4-bromophenyl group, 3-propoxy
Cyclocarbonylmethoxy-4-fluorophenyl group, 3-
Propoxycarbonylmethoxy-4-chlorophenyl
Group, 3-propoxycarbonylmethoxy-4-bromofu
Enyl group, 3-butoxycarbonylmethoxy-4-fur
Orophenyl group, 3-butoxycarbonylmethoxy-4
-Chlorophenyl group, 3-butoxycarbonylmethoxy
-4-bromophenyl group, 3-amyloxycarbonyl
Methoxy-4-fluorophenyl group, 3-amyloxy
Carbonylmethoxy-4-chlorophenyl group, 3-amido
A ruoxycarbonylmethoxy-4-bromophenyl group,
3-isopropoxycarbonylmethoxy-4-fluoro
Phenyl group, 3-isopropoxycarbonylmethoxy-
4-chlorophenyl group, 3-isopropoxycarbonyl
Methoxy-4-bromophenyl group, 3-cyclopentyl
An oxycarbonylmethoxy-4-fluorophenyl group,
3-cyclopentyloxycarbonylmethoxy-4-ku
Lorophenyl group, 3-cyclopentyloxycarbonyl
Methoxy-4-bromophenyl group, 3-cyclohexyl
An oxycarbonylmethoxy-4-fluorophenyl group,
3-cyclohexyloxycarbonylmethoxy-4-c
Lorophenyl group, 3-cyclohexyloxycarbonyl
A methoxy-4-bromophenyl group, 3-((1-carbo
(Xyethyl) oxy) -4-fluorophenyl group, 3-
((1-carboxyethyl) oxy) -4-chlorophen
Nyl group, 3-((1-carboxyethyl) oxy) -4
-Bromophenyl group, 3-((1-methoxycarbonyl
Ethyl) oxy) -4-fluorophenyl group, 3-
((1-methoxycarbonylethyl) oxy) -4-c
Lorophenyl group, 3-((1-methoxycarbonylethyl)
L) oxy) -4-bromophenyl group, 3-((1-E
Toxylcarbonylethyl) oxy) -4-fluorophen
Nyl group, 3-((1-ethoxycarbonylethyl) oxo
B) 4-chlorophenyl group, 3-((1-ethoxyca)
Rubonylethyl) oxy) -4-bromophenyl group, 3
-((1-propoxycarbonylethyl) oxy) -4
-Fluorophenyl group, 3-((1-propoxycarbo
Nylethyl) oxy) -4-chlorophenyl group, 3-
((1-propoxycarbonylethyl) oxy) -4-
Bromophenyl group, 3-((1-amyloxycarboni
Ruethyl) oxy) -4-fluorophenyl group, 3-
((1-amyloxycarbonylethyl) oxy) -4
-Chlorophenyl group, 3-((1-amyloxycarbo
Nylethyl) oxy) -4-bromophenyl group, 3-
((1-isopropoxycarbonylethyl) oxy)-
4-fluorophenyl group, 3-((1-isopropoxy
Carbonylethyl) oxy) -4-chlorophenyl group,
3-((1-isopropoxycarbonylethyl) oxo
B) -4-bromophenyl group, 3-((1-cyclopentene)
Tyloxycarbonylethyl) oxy) -4-fluoro
Phenyl group, 3-((1-cyclopentyloxycarbo
Nylethyl) oxy) -4-chlorophenyl group, 3-
((1-cyclopentyloxycarbonylethyl) oxy
B) 4-bromophenyl group, 3-((1-cyclohexyl)
Siloxycarbonylethyl) oxy) -4-fluoro
Phenyl group, 3-((1-cyclohexyloxycarbo
Nylethyl) oxy) -4-chlorophenyl group, 3-
((1-cyclohexyloxycarbonylethyl) oxo
B) 4-bromophenyl group, 3-aminocarbonyl
Toxic-4-fluorophenyl group, 3-aminocarboni
Methoxy-4-chlorophenyl group, 3-aminocarbo
Nilmethoxy-4-bromophenyl group, 3-methylamido
Nocarbonylmethoxy-4-fluorophenyl group, 3-
Methylaminocarbonylmethoxy-4-chlorophenyl
Group, 3-methylaminocarbonylmethoxy-4-bromo
Phenyl group, 3-dimethylaminocarbonylmethoxy-
4-fluorophenyl group, 3-dimethylaminocarboni
Methoxy-4-chlorophenyl group, 3-dimethylamido
Nocarbonylmethoxy-4-bromophenyl group, 3-di
Ethylaminocarbonylmethoxy-4-fluorophenyl
Group, 3-diethylaminocarbonylmethoxy-4-c
Lorophenyl group, 3-diethylaminocarbonyl methoxy
C-4-bromophenyl group, 3-methylethylaminoca
Rubonylmethoxy-4-fluorophenyl group, 3-methyl
Ruethylaminocarbonylmethoxy-4-chloropheni
Group, 3-methylethylaminocarbonylmethoxy-4
-Bromophenyl group, 3-((1-aminocarbonyl
Tyl) oxy) -4-fluorophenyl group, 3-((1
-Aminocarbonylethyl) oxy) -4-chlorophen
Nyl group, 3-((1-aminocarbonylethyl) oxo
B) 4-bromophenyl group, 3-((1-methylamido)
Noncarbonylethyl) oxy) -4-fluorophenyl
Group, 3-((1-methylaminocarbonylethyl) oxo
B) 4-chlorophenyl group, 3-((1-methylamido)
Noncarbonylethyl) oxy) -4-bromophenyl
Group, 3-((1-dimethylaminocarbonylethyl) O
Xy) -4-fluorophenyl group, 3-((1-dimethyl
Laminocarbonylethyl) oxy) -4-chlorophen
Nyl group, 3-((1-dimethylaminocarbonylethyl
L) oxy) -4-bromophenyl group, 3-((1-di
Ethylaminocarbonylethyl) oxy) -4-fluoro
Rophenyl group, 3-((1-diethylaminocarbonyl)
Ethyl) oxy) -4-chlorophenyl group, 3-((1
-Diethylaminocarbonylethyl) oxy) -4-bu
Lomophenyl group, 3-((1-ethylmethylaminocar
Bonylethyl) oxy) -4-fluorophenyl group, 3
-((1-ethylmethylaminocarbonylethyl) oxo
B) 4-chlorophenyl group, 3-((1-ethylmethyl
Laminocarbonylethyl) oxy) -4-bromofe
Nyl group, 3-dimethylaminooxycarbonylmethoxy
-4-fluorophenyl group, 3-dimethylaminooxy
Carbonylmethoxy-4-chlorophenyl group, 3-dimethyl
Tylaminooxycarbonylmethoxy-4-bromofe
Nyl group, 3-diethylaminooxycarbonylmethoxy
-4-fluorophenyl group, 3-diethylaminooxy
Carbonylmethoxy-4-chlorophenyl group, 3-die
Tylaminooxycarbonylmethoxy-4-bromofe
Nyl group, 3-methylthio-4-fluorophenyl group, 3
-Methylthio-4-chlorophenyl group, 3-methylthio
-4-bromophenyl group, 3-ethylthio-4-fluoro
Rophenyl group, 3-ethylthio-4-chlorophenyl
Group, 3-ethylthio-4-bromophenyl group, 3-iso
Propylthio-4-fluorophenyl group, 3-isopro
Pyrthio-4-chlorophenyl group, 3-isopropylthio group
O-4-bromophenyl group, 3- (2-chloroethylthio)
E) -4-fluorophenyl group, 3- (2-chloroethyl) group
Ruthio) -4-chlorophenyl group, 3- (2-chloroe
Tylthio) -4-bromophenyl group, 3-cyclopentene
Luthio-4-fluorophenyl group, 3-cyclopentyl
Thio-4-chlorophenyl group, 3-cyclopentylthio
-4-bromophenyl group, 3-cyclohexylthio-4
-Fluorophenyl group, 3-cyclohexylthio-4-
Chlorophenyl group, 3-cyclohexylthio-4-bro
Mophenyl group, 3-allylthio-4-fluorophenyl
Group, 3-allylthio-4-chlorophenyl group, 3-ali
Luthio-4-bromophenyl group, 3- (2-chloro-2
-Propenylthio) -4-fluorophenyl group, 3-
(2-chloro-2-propenylthio) -4-chlorophen
Nyl group, 3- (2-chloro-2-propenylthio) -4
-Bromophenyl group, 3- (2,3-dichloro-2-propyl)
Lophenylthio) -4-fluorophenyl group, 3- (2,
3-dichloro-2-propenylthio) -4-chlorophen
A 3- (2,3-dichloro-2-propenyl)
E) -4-bromophenyl group, 3- (1-methyl-2-
Propenylthio) -4-fluorophenyl group, 3- (1
-Methyl-2-propenylthio) -4-chlorophenyl
Group, 3- (1-methyl-2-propenylthio) -4-bu
Lomophenyl group, 3-propargylthio-4-fluoro
Phenyl group, 3-propargylthio-4-chlorophenyl
A 3-propargylthio-4-bromophenyl group;
3- (1-methyl-2-propynylthio) -4-fluoro
Rophenyl group, 3- (1-methyl-2-propynyl)
E) -4-chlorophenyl group, 3- (1-methyl-2-
Propynylthio) -4-bromophenyl group, 3-carbo
Xymethylthio-4-fluorophenyl group, 3-carbo
Xymethylthio-4-chlorophenyl group, 3-carboxy
Cimethylthio-4-bromophenyl group, 3-methoxyca
Rubornylmethylthio-4-fluorophenyl group,
A methoxycarbonylmethylthio-4-chlorophenyl group,
3-methoxycarbonylmethylthio-4-bromopheni
Group, 3-ethoxycarbonylmethylthio-4-fluoro
Rophenyl group, 3-ethoxycarbonylmethylthio-4
-Chlorophenyl group, 3-ethoxycarbonylmethylthio
O-4-bromophenyl group, 3-propoxycarbonyl
Methylthio-4-fluorophenyl group, 3-propoxy
Carbonylmethylthio-4-chlorophenyl group, 3-p
Ropoxycarbonylmethylthio-4-bromophenyl
Group, 3-butoxycarbonylmethylthio-4-fluoro
Phenyl group, 3-butoxycarbonylmethylthio-4-
Chlorophenyl group, 3-butoxycarbonylmethylthio
-4-bromophenyl group, 3-amyloxycarbonyl
Methylthio-4-fluorophenyl group, 3-amyloxo
Cicarbonylmethylthio-4-chlorophenyl group, 3-
Amyloxycarbonylmethylthio-4-bromopheni
Group, 3-isopropoxycarbonylmethylthio-4-
Fluorophenyl group, 3-isopropoxycarbonyl
Tylthio-4-chlorophenyl group, 3-isopropoxy
Carbonylmethylthio-4-bromophenyl group, 3-cy
Clopentyloxycarbonylmethylthio-4-fluoro
Rophenyl group, 3-cyclopentyloxycarbonyl
Tylthio-4-chlorophenyl group, 3-cyclopentyl
An oxycarbonylmethylthio-4-bromophenyl group,
3-cyclohexyloxycarbonylmethylthio-4-
Fluorophenyl group, 3-cyclohexyloxycarbo
Nylmethylthio-4-chlorophenyl group, 3-cyclohexyl
Xyloxycarbonylmethylthio-4-bromopheni
Group, 3-((1-carboxyethyl) thio) -4-f
A fluorophenyl group, 3-((1-carboxyethyl) thio
E) -4-chlorophenyl group, 3-((1-carboxy
Ethyl) thio) -4-bromophenyl group, 3-((1-
Methoxycarbonylethyl) thio) -4-fluorophene
Nyl group, 3-((1-methoxycarbonylethyl) thio
E) -4-chlorophenyl group, 3-((1-methoxyca)
Rubonylethyl) thio) -4-bromophenyl group, 3-
((1-ethoxycarbonylethyl) thio) -4-fur
Orophenyl group, 3-((1-ethoxycarbonylethyl
L) thio) -4-chlorophenyl group, 3-((1-ethy
Xycarbonylethyl) thio) -4-bromophenyl
Group, 3-((1-propoxycarbonylethyl) thio)
-4-fluorophenyl group, 3-((1-propoxyca
Rubonylethyl) thio) -4-chlorophenyl group, 3-
((1-propoxycarbonylethyl) thio) -4-bu
Lomophenyl group, 3-((1-butoxycarbonylethyl
L) thio) -4-fluorophenyl group, 3-((1-
Toxylcarbonylethyl) thio) -4-chlorophenyl
Group, 3-((1-butoxycarbonylethyl) thio)-
4-bromophenyl group, 3-((1-amyloxycal
Bonylethyl) thio) -4-fluorophenyl group, 3-
((1-amyloxycarbonylethyl) thio) -4-
Chlorophenyl group, 3-((1-amyloxycarboni
Ruethyl) thio) -4-bromophenyl group, 3-((1
-Cyclohexyloxycarbonylethyl) thio) -4
-Fluorophenyl group, 3-((1-cyclohexylo
Xycarbonylethyl) thio) -4-chlorophenyl
Group, 3-((1-cyclohexyloxycarbonylethyl)
L) thio) -4-bromophenyl group, 3-((1-cyclohexyl)
Lopentyloxycarbonylethyl) thio) -4-fur
Orophenyl group, 3-((1-cyclopentyloxyca
Rubonylethyl) thio) -4-chlorophenyl group, 3-
((1-cyclopentyloxycarbonylethyl) thio
E) -4-bromophenyl group, 3-((1-isopropo
Xycarbonylethyl) thio) -4-fluorophenyl
Group, 3-((1-isopropoxycarbonylethyl) thio
E) -4-chlorophenyl group, 3-((1-isopropo
Xycarbonylethyl) thio) -4-bromophenyl
Group, 3-aminocarbonylmethylthio-4-fluorop
Enyl group, 3-aminocarbonylmethylthio-4-chloro
Rophenyl group, 3-aminocarbonylmethylthio-4-
Bromophenyl group, 3-methylaminocarbonylmethyl
Thio-4-fluorophenyl group, 3-methylaminocar
Bonylmethylthio-4-chlorophenyl group, 3-methyl
Aminocarbonylmethylthio-4-bromophenyl group,
3-dimethylaminocarbonylmethylthio-4-fluoro
Rophenyl group, 3-dimethylaminocarbonylmethylthio
O-4-chlorophenyl group, 3-dimethylaminocarbo
Nylmethylthio-4-bromophenyl group, 3-diethyl
Aminocarbonylmethylthio-4-fluorophenyl
Group, 3-diethylaminocarbonylmethylthio-4-c
Lorophenyl group, 3-diethylaminocarbonylmethyl
Thio-4-bromophenyl group, 3-ethylmethylamino
Carbonylmethylthio-4-fluorophenyl group, 3-
Ethylmethylaminocarbonylmethylthio-4-chloro
Phenyl group, 3-ethylmethylaminocarbonylmethyl
Thio-4-bromophenyl group, 3-((1-aminocar
Bonylethyl) thio) -4-fluorophenyl group, 3-
((1-aminocarbonylethyl) thio) -4-chloro
Phenyl group, 3-((1-aminocarbonylethyl) thio
E) -4-bromophenyl group, 3-((1-methylamido)
Nocarbonylethyl) thio) -4-fluorophenyl
Group, 3-((1-methylaminocarbonylethyl) thio
E) -4-chlorophenyl group, 3-((1-methylamido)
Noncarbonylethyl) thio) -4-bromophenyl group,
3-((1-dimethylaminocarbonylethyl) thio)
-4-fluorophenyl group, 3-((1-dimethylamido
Nocarbonylcarbonyl) thio) -4-chlorophenyl group,
3-((1-dimethylaminocarbonylethyl) thio)
-4-bromophenyl group, 3-((1-diethylamino
Carbonylethyl) thio) -4-fluorophenyl group,
3-((1-diethylaminocarbonylethyl) thio)
-4-chlorophenyl group, 3-((1-diethylamino
Carbonylethyl) thio) -4-bromophenyl group, 3
-((1-ethylmethylaminocarbonylethyl) thio
E) -4-fluorophenyl group, 3-((1-ethylmeth
Tylaminocarbonylethyl) thio) -4-chlorophen
A 3-((1-ethylmethylaminocarbonyl)
Tyl) thio) -4-bromophenyl group, 3-methoxys
Rufonyl-4-fluorophenyl group, 3-methoxysul
Phonyl-4-chlorophenyl group, 3-methoxysulfoni
4-bromophenyl group, 3-ethoxysulfonyl-
4-fluorophenyl group, 3-ethoxysulfonyl-4
-Chlorophenyl group, 3-ethoxysulfonyl-4-bu
Lomophenyl group, 3-isopropoxysulfonyl-4-
Fluorophenyl group, 3-isopropoxysulfonyl-
4-chlorophenyl group, 3-isopropoxysulfonyl
-4-bromophenyl group, 3-allyloxysulfonyl
-4-fluorophenyl group, 3-allyloxysulfoni
4-chlorophenyl group, 3-allyloxysulfoni
4-bromophenyl group, 3-dimethylaminosulfo
Nyl-4-fluorophenyl group, 3-dimethylaminos
Ruphonyl-4-chlorophenyl group, 3-dimethylamino
Sulfonyl-4-bromophenyl group, 3-diethylamido
Nosulfonyl-4-fluorophenyl group, 3-diethyl
Aminosulfonyl-4-chlorophenyl group, 3-diethyl
Luminosulfonyl-4-bromophenyl group, 3-cal
Boxy-4-fluorophenyl group, 3-carboxy-4
-Chlorophenyl group, 3-carboxy-4-bromofe
Nyl group, 3-methoxycarbonyl-4-fluorophenyl
Group, 3-methoxycarbonyl-4-chlorophenyl
Group, 3-methoxycarbonyl-4-bromophenyl group,
3-ethoxycarbonyl-4-fluorophenyl group, 3
-Ethoxycarbonyl-4-chlorophenyl group, 3-E
Toxicarbonyl-4-bromophenyl group, 3-propo
Xycarbonyl-4-fluorophenyl group, 3-propo
Xycarbonyl-4-chlorophenyl group, 3-propoxy
Cicarbonyl-4-bromophenyl group, 3-butoxyca
Rubonyl-4-fluorophenyl group, 3-butoxycal
Bonyl-4-chlorophenyl group, 3-butoxycarboni
4-bromophenyl group, 3-amyloxycarbonyl
4-fluorophenyl group, 3-amyloxycarbo
Nyl-4-chlorophenyl group, 3-amyloxycarbo
Nyl-4-bromophenyl group, 3-isopropoxy
Bonyl-4-fluorophenyl group, 3-isopropoxy
Carbonyl-4-chlorophenyl group, 3-isopropoxy
Cicarbonyl-4-bromophenyl group, 3-cyclopen
Tyloxycarbonyl-4-fluorophenyl group, 3-
Cyclopentyloxycarbonyl-4-chlorophenyl
Group, 3-cyclopentyloxycarbonyl-4-bromo
Phenyl group, 3-cyclohexyloxycarbonyl-4
-Fluorophenyl group, 3-cyclohexyloxycal
Bonyl-4-chlorophenyl group, 3-cyclohexylo
Xycarbonyl-4-bromophenyl group, 3-benzyl
Oxycarbonyl-4-fluorophenyl group, 3-ben
A ziroxycarbonyl-4-chlorophenyl group,
Benzyloxycarbonyl-4-bromophenyl group, 3-
(2-chloroethoxycarbonyl) -4-fluorophene
Nyl group, 3- (2-chloroethoxycarbonyl) -4-
Chlorophenyl group, 3- (2-chloroethoxycarbonyl)
) -4-bromophenyl group, 3- (2-bromoethoxy)
(Cyclocarbonyl) -4-fluorophenyl group, 3- (2-
Bromoethoxycarbonyl) -4-chlorophenyl group,
3- (2-bromoethoxycarbonyl) -4-bromofu
Phenyl group, 3-aminocarbonyl-4-fluorophenyl
Group, 3-aminocarbonyl-4-chlorophenyl group,
3-aminocarbonyl-4-bromophenyl group,
Tylaminocarbonyl-4-fluorophenyl group, 3-
Methylaminocarbonyl-4-chlorophenyl group, 3-
Methylaminocarbonyl-4-bromophenyl group, 3-
Ethylaminocarbonyl-4-fluorophenyl group, 3
-Ethylaminocarbonyl-4-chlorophenyl group, 3
-Ethylaminocarbonyl-4-bromophenyl group, 3
-Dimethylaminocarbonyl-4-fluorophenyl
Group, 3-dimethylaminocarbonyl-4-chlorophenyl
Group, 3-dimethylaminocarbonyl-4-bromofe
Nyl group, 3-diethylaminocarbonyl-4-fluoro
Phenyl group, 3-diethylaminocarbonyl-4-chloro
Rophenyl group, 3-diethylaminocarbonyl-4-bu
Lomophenyl group, 3-ethylmethylaminocarbonyl-
4-fluorophenyl group, 3-ethylmethylaminocar
Bonyl-4-chlorophenyl group, 3-ethylmethylamido
Nocarbonyl-4-bromophenyl group, 3-methylcar
Bonyl-4-fluorophenyl group, 3-methylcarbonyl
4-chlorophenyl group, 3-methylcarbonyl-4
-Bromophenyl group, 3-ethylcarbonyl-4-fur
Orophenyl group, 3-ethylcarbonyl-4-chlorofu
Phenyl group, 3-ethylcarbonyl-4-bromophenyl
Group, 3-chloromethylcarbonyl-4-fluorophenyl
Group, 3-chloromethylcarbonyl-4-chlorophenyl
Group, 3-chloromethylcarbonyl-4-bromophenyi
Group, 3-formyl-4-fluorophenyl group, 3-
Lumyl-4-chlorophenyl group, 3-formyl-4-bu
Lomophenyl group, 3- (2-carboxyethyl) -4-
Fluorophenyl group, 3- (2-carboxyethyl)-
4-chlorophenyl group, 3- (2-carboxyethyl)
-4-bromophenyl group, 3- (2-methoxycarbonyl)
Ruethyl) -4-fluorophenyl group, 3- (2-meth
(Oxycarbonylethyl) -4-chlorophenyl group, 3-
(2-methoxycarbonylethyl) -4-bromophenyi
Group, 3- (2-ethoxycarbonylethyl) -4-f
A fluorophenyl group, 3- (2-ethoxycarbonylethyl)
L) -4-chlorophenyl group, 3- (2-ethoxycal
Bonylethyl) -4-bromophenyl group, 3- (2-k
(Rolo-2-methoxycarbonylethyl) -4-fluoro
Phenyl group, 3- (2-chloro-2-methoxycarbonyl)
Ruethyl) -4-chlorophenyl group, 3- (2-chloro
-2-methoxycarbonylethyl) -4-bromophenyi
Group, 3- (2-chloro-2-ethoxycarbonylethyl)
L) -4-fluorophenyl group, 3- (2-chloro-2)
-Ethoxycarbonylethyl) -4-chlorophenyl
Group, 3- (2-chloro-2-ethoxycarbonylethyl)
L) -4-bromophenyl group, 3- (2-methoxycal
Bonylvinyl) -4-fluorophenyl group, 3- (2-
Methoxycarbonylvinyl) -4-chlorophenyl group,
3- (2-methoxycarbonylvinyl) -4-bromofur
Enyl group, 3- (2-ethoxycarbonylvinyl) -4
-Fluorophenyl group, 3- (2-ethoxycarbonyl
Vinyl) -4-chlorophenyl group, 3- (2-ethoxy)
Carbonylvinyl) -4-bromophenyl group, 3-methoxy
Xycarbonylmethoxycarbonyl-4-fluorophene
Nyl group, 3-methoxycarbonylmethoxycarbonyl-
4-chlorophenyl group, 3-methoxycarbonyl methoxy
Cicarbonyl-4-bromophenyl group, 3-ethoxyca
Rubonylmethoxycarbonyl-4-fluorophenyl
Group, 3-ethoxycarbonylmethoxycarbonyl-4-
Chlorophenyl group, 3-ethoxycarbonylmethoxyca
Rubonyl-4-bromophenyl group, 3- (1-methoxy
Carbonylethoxy) carbonyl-4-fluorophenyl
Group, 3- (1-methoxycarbonylethoxy) carbo
Nil-4-chlorophenyl group, 3- (1-methoxycal
Bonylethoxy) carbonyl-4-bromophenyl group,
3- (1-ethoxycarbonylethoxy) carbonyl-
4-fluorophenyl group, 3- (1-ethoxycarbonyl)
Ruethoxy) carbonyl-4-chlorophenyl group, 3-
(1-ethoxycarbonylethoxy) carbonyl-4-
Bromophenyl group,

2,4-difluorophenyl group, 4-chloro
B-2-fluorophenyl group, 4-bromo-2-fluoro
Rophenyl group, 2,4-difluoro-5-nitrophenyl
Group, 4-chloro-2-fluoro-5-nitrophenyl
Group, 4-bromo-2-fluoro-5-nitrophenyl
Group, 5-amino-2,4-difluorophenyl group, 5-
Amino-4-chloro-2-fluorophenyl group, 5-A
Mino-4-bromo-2-fluorophenyl group, 5-hydrido
Roxy-2,4-difluorophenyl group, 5-hydroxy
Ci-4-chloro-2-fluorophenyl group, 5-hydro
Xy-4-bromo-2-fluorophenyl group, 5-mer
Capto-2,4-difluorophenyl group, 5-mercap
To-4-chloro-2-fluorophenyl group, 5-merca
Pt-4-bromo-2-fluorophenyl group, 5-chloro
Losulfonyl-2,4-difluorophenyl group, 5-
Lorosulfonyl-4-chloro-2-fluorophenyl
Group, 5-chlorosulfonyl-4-bromo-2-fluoro
Phenyl group, 5-methylamino-2,4-difluorophenyl
Enyl group, 5-methylamino-4-chloro-2-fluoro
Rophenyl group, 5-methylamino-4-bromo-2-f
Fluorophenyl group, 5-ethylamino-2,4-difur
Orophenyl group, 5-ethylamino-4-chloro-2-
Fluorophenyl group, 5-ethylamino-4-bromo-
2-fluorophenyl group, 5-allylamino-2,4-
Difluorophenyl group, 5-allylamino-4-chloro
-2-fluorophenyl group, 5-allylamino-4-bu
Lomo-2-fluorophenyl group, 5-propargylamido
No-2,4-difluorophenyl group, 5-propargyl
Amino-4-chloro-2-fluorophenyl group, 5-p
Lopargylamino-4-bromo-2-fluorophenyl
The group 5- (1-methyl-2-propynylamino) -2,
4-difluorophenyl group, 5- (1-methyl-2-propyl)
Lopinylamino) -4-chloro-2-fluorophenyl
Group 5- (1-methyl-2-propynylamino) -4-
Bromo-2-fluorophenyl group, 5-methanesulfoni
Ruamino-2,4-difluorophenyl group, 5-methane
Sulfonylamino-4-chloro-2-fluorophenyl
Group, 5-methanesulfonylamino-4-bromo-2-f
A fluorophenyl group, 5-ethanesulfonylamino-2,
4-difluorophenyl group, 5-ethanesulfonylamido
No-4-chloro-2-fluorophenyl group, 5-ethane
Sulfonylamino-4-bromo-2-fluorophenyl
Group, 5-chloromethanesulfonylamino-2,4-diph
Fluorophenyl group, 5-chloromethanesulfonylamino
-4-chloro-2-fluorophenyl group, 5-chloromethyl
Tansulfonylamino-4-bromo-2-fluorophene
Nil group, 5-trifluoromethanesulfonylamino-
2,4-difluorophenyl group, 5-trifluorometa
Sulfonylamino-4-chloro-2-fluorophenyl
Group, 5-trifluoromethanesulfonylamino-4-
Bromo-2-fluorophenyl group, 5- (dimethanesulfur
Honylamino) -2,4-difluorophenyl group, 5-
(Dimethanesulfonylamino) -4-chloro-2-fur
Orophenyl group, 5- (dimethanesulfonylamino)-
4-bromo-2-fluorophenyl group, 5- (methanes
Rufonyl (methyl) amino) -2,4-difluorophene
Nyl group, 5- (methanesulfonyl (methyl) amino)-
4-chloro-2-fluorophenyl group, 5- (methanes
Ruphonyl (methyl) amino) -4-bromo-2-fluoro
Rophenyl group, 5- (methanesulfonyl (propargy
L) amino) -2,4-difluorophenyl group, 5-
(Methanesulfonyl (propargyl) amino) -4-c
Rolo-2-fluorophenyl group, 5- (methanesulfoni
(Propargyl) amino) -4-bromo-2-fluoro
Rophenyl group, 5-methoxycarbonylamino-2,4
-Difluorophenyl group, 5-methoxycarbonylamido
No-4-chloro-2-fluorophenyl group, 5-methoxy
Cicarbonylamino-4-bromo-2-fluorophenyl
Group, 5-ethoxycarbonylamino-2,4-difur
Orophenyl group, 5-ethoxycarbonylamino-4-
Chloro-2-fluorophenyl group, 5-ethoxycarbo
Nilamino-4-bromo-2-fluorophenyl group, 5
-Propoxycarbonylamino-2,4-difluorop
Enyl group, 5-propoxycarbonylamino-4-chloro
B-2-fluorophenyl group, 5-propoxycarbonyl
Rumin-4-bromo-2-fluorophenyl group, 5-
Isopropoxycarbonylamino-2,4-difluoro
Phenyl group, 5-isopropoxycarbonylamino-4
-Chloro-2-fluorophenyl group, 5-isopropoxy
Cicarbonylamino-4-bromo-2-fluorophenyl
Group, 5-butoxycarbonylamino-2,4-difur
Orophenyl group, 5-butoxycarbonylamino-4-
Chloro-2-fluorophenyl group, 5-butoxycarbo
Nilamino-4-bromo-2-fluorophenyl group, 5
-Amyloxycarbonylamino-2,4-difluoro
Phenyl group, 5-amyloxycarbonylamino-4-
Chloro-2-fluorophenyl group, 5-amyloxyca
Rubonylamino-4-bromo-2-fluorophenyl
Group, 5-methoxycarbonylmethylamino-2,4-di
Fluorophenyl group, 5-methoxycarbonylmethyla
Mino-4-chloro-2-fluorophenyl group, 5-metho
Xycarbonylmethylamino-4-bromo-2-fluoro
Rophenyl group, 5-ethoxycarbonylmethylamino-
2,4-difluorophenyl group, 5-ethoxycarboni
Methylamino-4-chloro-2-fluorophenyl
Group, 5-ethoxycarbonylmethylamino-4-bromo
-2-fluorophenyl group, 5-propoxycarbonyl
Methylamino-2,4-difluorophenyl group, 5-p
Ropoxycarbonylmethylamino-4-chloro-2-fu
Fluorophenyl group, 5-propoxycarbonylmethyla
Mino-4-bromo-2-fluorophenyl group, 5-buto
Xycarbonylmethylamino-2,4-difluorofe
Nyl group, 5-butoxycarbonylmethylamino-4-c
Loro-2-fluorophenyl group, 5-butoxycarboni
Methylamino-4-bromo-2-fluorophenyl
Group, 5-amyloxycarbonylmethylamino-2,4
-Difluorophenyl group, 5-amyloxycarbonyl
A methylamino-4-chloro-2-fluorophenyl group,
5-amyloxycarbonylmethylamino-4-bromo
-2-fluorophenyl group, 5-isopropoxycarbo
Nylmethylamino-2,4-difluorophenyl group, 5
-Isopropoxycarbonylmethylamino-4-chloro
-2-fluorophenyl group, 5-isopropoxycarbo
Nylmethylamino-4-bromo-2-fluorophenyl
Group, 5-cyclopentyloxycarbonylmethylamino
-2,4-difluorophenyl group, 5-cyclopentyl
Oxycarbonylmethylamino-4-chloro-2-fur
Orophenyl group, 5-cyclopentyloxycarbonyl
A methylamino-4-bromo-2-fluorophenyl group,
5-cyclohexyloxycarbonylmethylamino-
2,4-difluorophenyl group, 5-cyclohexylo
Xycarbonylmethylamino-4-chloro-2-fluoro
Rophenyl group, 5-cyclohexyloxycarbonyl
Tylamino-4-bromo-2-fluorophenyl group, 5
-((1-methoxycarbonylethyl) amino) -2,
4-difluorophenyl group, 5-((1-methoxycal
Bonylethyl) amino) -4-chloro-2-fluoroph
Enyl group, 5-((1-methoxycarbonylethyl) a
Mino) -4-bromo-2-fluorophenyl group, 5-
((1-ethoxycarbonylethyl) amino) -2,4
-Difluorophenyl group, 5-((1-ethoxycarbo
Nylethyl) amino) -4-chloro-2-fluorophene
Nyl group, 5-((1-ethoxycarbonylethyl) amido
No) 4-bromo-2-fluorophenyl group, 5-
((1-propoxycarbonylethyl) amino) -2,
4-difluorophenyl group, 5-((1-propoxyca
Rubonylethyl) amino) -4-chloro-2-fluoro
Phenyl group, 5-((1-propoxycarbonylethyl
L) amino) -4-bromo-2-fluorophenyl group,
5-((1-butoxycarbonylethyl) amino)-
2,4-difluorophenyl group, 5-((1-butoxy
Carbonylethyl) amino) -4-chloro-2-fluoro
Rophenyl group, 5-((1-butoxycarbonylethyl
L) amino) -4-bromo-2-fluorophenyl group,
5-((1-amyloxycarbonylethyl) amino)
-2,4-difluorophenyl group, 5-((1-amyl
(Oxycarbonylethyl) amino) -4-chloro-2-
Fluorophenyl group, 5-((1-amyloxycarbo
Nylethyl) amino) -4-bromo-2-fluorophene
5-((1-isopropoxycarbonylethyl)
L) amino) -2,4-difluorophenyl group, 5-
((1-isopropoxycarbonylethyl) amino)-
4-chloro-2-fluorophenyl group, 5-((1-i
Sopropoxycarbonylethyl) amino) -4-bromo
-2-fluorophenyl group, 5-((1-cyclopentene
Ruoxycarbonylethyl) amino) -2,4-diflu
Orophenyl group, 5-((1-cyclopentyloxyca
Rubonylethyl) amino) -4-chloro-2-fluoro
Phenyl group, 5-((1-cyclopentyloxycarbo
Nylethyl) amino) -4-bromo-2-fluorophene
5-((1-cyclohexyloxycarbonyl)
Ethyl) amino) -2,4-difluorophenyl group, 5
-((1-cyclohexyloxycarbonylethyl) a
Mino) -4-chloro-2-fluorophenyl group, 5-
((1-cyclohexyloxycarbonylethyl) amido
No) 4-bromo-2-fluorophenyl group, 5-metho
Xy-2,4-difluorophenyl group, 5-methoxy-
4-chloro-2-fluorophenyl group, 5-methoxy-
4-bromo-2-fluorophenyl group, 5-ethoxy-
2,4-difluorophenyl group, 5-ethoxy-4-c
Loro-2-fluorophenyl group, 5-ethoxy-4-bu
Lomo-2-fluorophenyl group, 5-isopropoxy-
2,4-difluorophenyl group, 5-isopropoxy-
4-chloro-2-fluorophenyl group, 5-isopropo
Xy-4-bromo-2-fluorophenyl group, 5-pro
Poxy-2,4-difluorophenyl group, 5-propoxy
C-4-chloro-2-fluorophenyl group, 5-propo
Xy-4-bromo-2-fluorophenyl group, 5- (2
-Chloroethoxy) -2,4-difluorophenyl group,
5- (2-chloroethoxy) -4-chloro-2-fluoro
Rophenyl group, 5- (2-chloroethoxy) -4-bro
Mo-2-fluorophenyl group, 5- (1,1,2,2-
Tetrafluoroethoxy) -2,4-difluorophenyl
Group, 5- (1,1,2,2-tetrafluoroethoxy)
B) -4-chloro-2-fluorophenyl group, 5-
(1,1,2,2-tetrafluoroethoxy) -4-bu
Lomo-2-fluorophenyl group, 5-cyclopentylo
Xy-2,4-difluorophenyl group, 5-cyclopen
Tyloxy-4-chloro-2-fluorophenyl group, 5
-Cyclopentyloxy-4-bromo-2-fluoroph
Enyl group, 5-cyclohexyloxy-2,4-difur
Orophenyl group, 5-cyclohexyloxy-4-chloro
B-2-fluorophenyl group, 5-cyclohexyloxy
Ci-4-bromo-2-fluorophenyl group, 5-allyl
Oxy-2,4-difluorophenyl group, 5-allyluo
Xy-4-chloro-2-fluorophenyl group, 5-ali
Luoxy-4-bromo-2-fluorophenyl group, 5-
(2-chloro-2-propenyloxy) -2,4-diph
A fluorophenyl group, 5- (2-chloro-2-propenyl)
Oxy) -4-chloro-2-fluorophenyl group, 5-
(2-chloro-2-propenyloxy) -4-bromo-
2-fluorophenyl group, 5- (2,5-dichloro-2
-Propenyloxy) -2,4-difluorophenyl
Group, 5- (2,5-dichloro-2-propenyloxy)
-4-chloro-2-fluorophenyl group, 5- (2,5
-Dichloro-2-propenyloxy) -4-bromo-2
-Fluorophenyl group, 5- (2-methyl-2-prope)
Nyloxy) -2,4-difluorophenyl group, 5-
(2-methyl-2-propenyloxy) -4-chloro-
2-fluorophenyl group, 5- (2-methyl-2-pro
Penyloxy) -4-bromo-2-fluorophenyl
The group 5- (1-methyl-2-propenyloxy) -2,
4-difluorophenyl group, 5- (1-methyl-2-propyl)
Lopenyloxy) -4-chloro-2-fluorophenyl
Group 5- (1-methyl-2-propenyloxy) -4-
Bromo-2-fluorophenyl group, 5-propargylo
Xy-2,4-difluorophenyl group, 5-propargy
A luoxy-4-chloro-2-fluorophenyl group, 5-
Propargyloxy-4-bromo-2-fluorophenyl
Group, 5- (1-methyl-2-propynyloxy)-
2,4-difluorophenyl group, 5- (1-methyl-2
-Propynyloxy) -4-chloro-2-fluorophene
Nyl group, 5- (1-methyl-2-propynyloxy)-
4-bromo-2-fluorophenyl group, 5- (5-bromo
Mo-2-propynyloxy) -2,4-difluorophene
Nyl group, 5- (5-bromo-2-propynyloxy)-
4-chloro-2-fluorophenyl group, 5- (5-bromo
Mo-2-propynyloxy) -4-bromo-2-fluoro
Rophenyl group, 5- (5-chloro-2-propynyloxy)
B) -2,4-difluorophenyl group, 5- (5-chloro
B-2-propynyloxy) -4-chloro-2-fluoro
Rophenyl group, 5- (5-chloro-2-propynyloxy)
B) 4-bromo-2-fluorophenyl group, 5-sia
Nomethyloxy-2,4-difluorophenyl group, 5-
Cyanomethyloxy-4-chloro-2-fluorophenyl
Group, 5-cyanomethyloxy-4-bromo-2-fur
Orophenyl group, 5-methoxymethoxy-2,4-diph
Fluorophenyl group, 5-methoxymethoxy-4-chloro
-2-fluorophenyl group, 5-methoxymethoxy-4
-Bromo-2-fluorophenyl group, 5-ethoxymeth
Xy-2,4-difluorophenyl group, 5-ethoxyme
A toxic-4-chloro-2-fluorophenyl group, 5-E
Toximethoxy-4-bromo-2-fluorophenyl
Group, 5-methylthiomethyloxy-2,4-difluoro
Phenyl group, 5-methylthiomethyloxy-4-chloro
-2-fluorophenyl group, 5-methylthiomethyloxy
C-4-bromo-2-fluorophenyl group, 5-carbo
Xymethoxy-2,4-difluorophenyl group, 5-ca
Ruboxymethoxy-4-chloro-2-fluorophenyl
Group, 5-carboxymethoxy-4-bromo-2-fluoro
Rophenyl group, 5-methoxycarbonylmethoxy-2,
4-difluorophenyl group, 5-methoxycarbonyl
Toxic-4-chloro-2-fluorophenyl group, 5-me
Toxylcarbonylmethoxy-4-bromo-2-fluoro
Phenyl group, 5-ethoxycarbonylmethoxy-2,4
-Difluorophenyl group, 5-ethoxycarbonylmetho
Xy-4-chloro-2-fluorophenyl group, 5-ethoxy
Xycarbonylmethoxy-4-bromo-2-fluorop
Enyl group, 5-propoxycarbonylmethoxy-2,4
-Difluorophenyl group, 5-propoxycarbonyl
Toxic-4-chloro-2-fluorophenyl group, 5-p
Ropoxycarbonylmethoxy-4-bromo-2-fluoro
Rophenyl group, 5-butoxycarbonylmethoxy-2,
4-difluorophenyl group, 5-butoxycarbonyl
Toxic-4-chloro-2-fluorophenyl group, 5-bu
Toxylcarbonylmethoxy-4-bromo-2-fluoro
Phenyl group, 5-amyloxycarbonylmethoxy-
2,4-difluorophenyl group, 5-amyloxycal
Bonylmethoxy-4-chloro-2-fluorophenyl
Group, 5-amyloxycarbonylmethoxy-4-bromo
-2-fluorophenyl group, 5-isopropoxycarbo
Nilmethoxy-2,4-difluorophenyl group, 5-i
Sopropoxycarbonylmethoxy-4-chloro-2-f
Fluorophenyl group, 5-isopropoxycarbonyl meth
Xy-4-bromo-2-fluorophenyl group, 5-cycl
Lopentyloxycarbonylmethoxy-2,4-difur
Orophenyl group, 5-cyclopentyloxycarbonyl
Methoxy-4-chloro-2-fluorophenyl group, 5-
Cyclopentyloxycarbonylmethoxy-4-bromo
-2-fluorophenyl group, 5-cyclohexyloxy
A carbonylmethoxy-2,4-difluorophenyl group,
5-cyclohexyloxycarbonylmethoxy-4-ku
Loro-2-fluorophenyl group, 5-cyclohexylo
Xycarbonylmethoxy-4-bromo-2-fluorop
Enyl group, 5-((1-carboxyethyl) oxy)-
2,4-difluorophenyl group, 5-((1-carboxy
Ciethyl) oxy) -4-chloro-2-fluorophenyl
Group, 5-((1-carboxyethyl) oxy) -4-
Bromo-2-fluorophenyl group, 5-((1-methoxy
(Cyclocarbonylethyl) oxy) -2,4-difluorop
Enyl group, 5-((1-methoxycarbonylethyl) o
Xy) -4-chloro-2-fluorophenyl group, 5-
((1-methoxycarbonylethyl) oxy) -4-bu
Lomo-2-fluorophenyl group, 5-((1-propoxy
(Cyclocarbonylethyl) oxy) -2,4-difluorop
Enyl group, 5-((1-propoxycarbonylethyl)
Oxy) -4-chloro-2-fluorophenyl group, 5-
((1-propoxycarbonylethyl) oxy) -4-
Bromo-2-fluorophenyl group, 5-((1-amyl
Oxycarbonylethyl) oxy) -2,4-difluoro
Rophenyl group, 5-((1-amyloxycarbonyl
Tyl) oxy) -4-chloro-2-fluorophenyl
Group, 5-((1-amyloxycarbonylethyl) oxo
B) 4-bromo-2-fluorophenyl group, 5-
((1-isopropoxycarbonylethyl) oxy)-
2,4-difluorophenyl group, 5-((1-isopro
Poxycarbonylethyl) oxy) -4-chloro-2-
Fluorophenyl group, 5-((1-isopropoxycal
Bonylethyl) oxy) -4-bromo-2-fluoroph
Enyl group, 5-((1-cyclopentyloxycarboni
Ruethyl) oxy) -2,4-difluorophenyl group,
5-((1-cyclopentyloxycarbonylethyl)
Oxy) -4-chloro-2-fluorophenyl group, 5-
((1-cyclopentyloxycarbonylethyl) oxy
B) 4-bromo-2-fluorophenyl group, 5-
((1-cyclohexyloxycarbonylethyl) oxo
C) -2,4-difluorophenyl group, 5-((1-c
Clohexyloxycarbonylethyl) oxy) -4-
Chloro-2-fluorophenyl group, 5-((1-cyclo
Hexyloxycarbonylethyl) oxy) -4-bro
Mo-2-fluorophenyl group, 5-aminocarbonyl
Toxic-2,4-difluorophenyl group, 5-aminoca
Rubonylmethoxy-4-chloro-2-fluorophenyl
Group, 5-aminocarbonylmethoxy-4-bromo-2-
Fluorophenyl group, 5-methylaminocarbonyl meth
Xy-2,4-difluorophenyl group, 5-methylamido
Nocarbonylmethoxy-4-chloro-2-fluorophene
Nyl group, 5-methylaminocarbonylmethoxy-4-bu
Lomo-2-fluorophenyl group, 5-dimethylaminoca
Rubonylmethoxy-2,4-difluorophenyl group, 5
-Dimethylaminocarbonylmethoxy-4-chloro-2
-Fluorophenyl group, 5-dimethylaminocarbonyl
Methoxy-4-bromo-2-fluorophenyl group, 5-
Diethylaminocarbonylmethoxy-2,4-difluoro
Rophenyl group, 5-diethylaminocarbonylmethoxy
-4-chloro-2-fluorophenyl group, 5-diethyl
Aminocarbonylmethoxy-4-bromo-2-fluoro
Phenyl group, 5-methylethylaminocarbonyl methoxy
C-2,4-difluorophenyl group, 5-methylethyl
Aminocarbonylmethoxy-4-chloro-2-fluoro
Phenyl group, 5-methylethylaminocarbonyl methoxy
C-4-bromo-2-fluorophenyl group, 5-((1
-Aminocarbonylethyl) oxy) -2,4-diflu
Orophenyl group, 5-((1-aminocarbonylethyl
L) oxy) -4-chloro-2-fluorophenyl group,
5-((1-aminocarbonylethyl) oxy) -4-
Bromo-2-fluorophenyl group, 5-((1-methyl
Aminocarbonylethyl) oxy) -2,4-difluoro
Rophenyl group, 5-((1-methylaminocarbonyl
Tyl) oxy) -4-chloro-2-fluorophenyl
Group, 5-((1-methylaminocarbonylethyl) oxo
B) 4-bromo-2-fluorophenyl group, 5-
((1-dimethylaminocarbonylethyl) oxy)-
2,4-difluorophenyl group, 5-((1-dimethyl
Aminocarbonylethyl) oxy) -4-chloro-2-
Fluorophenyl group, 5-((1-dimethylaminocar
Bonylethyl) oxy) -4-bromo-2-fluoroph
Enyl group, 5-((1-diethylaminocarbonylethyl)
L) oxy) -2,4-difluorophenyl group, 5-
((1-diethylaminocarbonylethyl) oxy)-
4-chloro-2-fluorophenyl group, 5-((1-di
Ethylaminocarbonylethyl) oxy) -4-bromo
-2-fluorophenyl group, 5-((1-ethylmethyl
Aminocarbonylethyl) oxy) -2,4-difluoro
Rophenyl group, 5-((1-ethylmethylaminocarbo
Nylethyl) oxy) -4-chloro-2-fluorophen
5-((1-ethylmethylaminocarbonyl)
Tyl) oxy) -4-bromo-2-fluorophenyl
Group, 5-dimethylaminooxycarbonylmethoxy-
2,4-difluorophenyl group, 5-dimethylamino
Xycarbonylcarbonyl-4-chloro-2-fluoroph
Enyl group, 5-dimethylaminooxycarbonyl methoxy
4-bromo-2-fluorophenyl group, 5-diethyl
L-aminooxycarbonylmethoxy-2,4-difluoro
Rophenyl group, 5-diethylaminooxycarbonyl
Toxic-4-chloro-2-fluorophenyl group, 5-di
Ethylaminooxycarbonylmethoxy-4-bromo-
2-fluorophenyl group, 5-methylthio-2,4-di
Fluorophenyl group, 5-methylthio-4-chloro-2
-Fluorophenyl group, 5-methylthio-4-bromo-
2-fluorophenyl group, 5-ethylthio-2,4-di
Fluorophenyl group, 5-ethylthio-4-chloro-2
-Fluorophenyl group, 5-ethylthio-4-bromo-
2-fluorophenyl group, 5-isopropylthio-2,
4-difluorophenyl group, 5-isopropylthio-4
-Chloro-2-fluorophenyl group, 5-isopropyl
Thio-4-bromo-2-fluorophenyl group, 5- (2
-Chloroethylthio) -2,4-difluorophenyl
Group, 5- (2-chloroethylthio) -4-chloro-2-
Fluorophenyl group, 5- (2-chloroethylthio)-
4-bromo-2-fluorophenyl group, 5-cyclopen
Tylthio-2,4-difluorophenyl group, 5-cyclo
A pentylthio-4-chloro-2-fluorophenyl group,
5-cyclopentylthio-4-bromo-2-fluoroph
Phenyl group, 5-cyclohexylthio-2,4-difluoro
Rophenyl group, 5-cyclohexylthio-4-chloro-
2-fluorophenyl group, 5-cyclohexylthio-4
-Bromo-2-fluorophenyl group, 5-allylthio-
2,4-difluorophenyl group, 5-allylthio-4-
Chloro-2-fluorophenyl group, 5-allylthio-4
-Bromo-2-fluorophenyl group, 5- (2-chloro
-2-propenylthio) -2,4-difluorophenyl
Group, 5- (2-chloro-2-propenylthio) -4-c
Rolo-2-fluorophenyl group, 5- (2-chloro-2
-Propenylthio) -4-bromo-2-fluorophenyl
Group, 5- (2,5-dichloro-2-propenylthio)
-2,4-difluorophenyl group, 5- (2,5-dic
(Rolo-2-propenylthio) -4-chloro-2-fluoro
Rophenyl group, 5- (2,5-dichloro-2-propeni)
Ruthio) -4-bromo-2-fluorophenyl group, 5-
(1-methyl-2-propenylthio) -2,4-difur
Orophenyl group, 5- (1-methyl-2-propenyl)
E) -4-chloro-2-fluorophenyl group, 5- (1
-Methyl-2-propenylthio) -4-bromo-2-f
Fluorophenyl group, 5-propargylthio-2,4-di
Fluorophenyl group, 5-propargylthio-4-chloro
B-2-fluorophenyl group, 5-propargylthio-
4-bromo-2-fluorophenyl group, 5- (1-methyl
2-propynylthio) -2,4-difluorophenyl
Group, 5- (1-methyl-2-propynylthio) -4-
Chloro-2-fluorophenyl group, 5- (1-methyl-
2-propynylthio) -4-bromo-2-fluorophene
Nyl group, 5-carboxymethylthio-2,4-difluoro
Rophenyl group, 5-carboxymethylthio-4-chloro
-2-fluorophenyl group, 5-carboxymethylthio
-4-bromo-2-fluorophenyl group, 5-methoxy
Carbonylmethylthio-2,4-difluorophenyl
Group, 5-methoxycarbonylmethylthio-4-chloro-
2-fluorophenyl group, 5-methoxycarbonylmethyl
Luthio-4-bromo-2-fluorophenyl group, 5-e
Toxylcarbonylmethylthio-2,4-difluorofe
Nyl group, 5-ethoxycarbonylmethylthio-4-chloro
B-2-fluorophenyl group, 5-ethoxycarbonyl
Methylthio-4-bromo-2-fluorophenyl group, 5
-Propoxycarbonylmethylthio-2,4-difluoro
Rophenyl group, 5-propoxycarbonylmethylthio-
4-chloro-2-fluorophenyl group, 5-propoxy
Carbonylmethylthio-4-bromo-2-fluorophene
Nyl group, 5-butoxycarbonylmethylthio-2,4-
Difluorophenyl group, 5-butoxycarbonylmethyl
Thio-4-chloro-2-fluorophenyl group, 5-but
Xycarbonylmethylthio-4-bromo-2-fluoro
Phenyl group, 5-amyloxycarbonylmethylthio-
2,4-difluorophenyl group, 5-amyloxycal
Bonylmethylthio-4-chloro-2-fluorophenyl
Group, 5-amyloxycarbonylmethylthio-4-bro
Mo-2-fluorophenyl group, 5-isopropoxycal
Bonylmethylthio-2,4-difluorophenyl group, 5
-Isopropoxycarbonylmethylthio-4-chloro-
2-fluorophenyl group, 5-isopropoxycarboni
A methylthio-4-bromo-2-fluorophenyl group,
5-cyclopentyloxycarbonylmethylthio-2,
4-difluorophenyl group, 5-cyclopentyloxy
Carbonylmethylthio-4-chloro-2-fluorophene
Nyl group, 5-cyclopentyloxycarbonylmethylthio
O-4-bromo-2-fluorophenyl group, 5-cyclo
Hexyloxycarbonylmethylthio-2,4-difur
Orophenyl group, 5-cyclohexyloxycarbonyl
Methylthio-4-chloro-2-fluorophenyl group, 5
-Cyclohexyloxycarbonylmethylthio-4-bu
Lomo-2-fluorophenyl group, 5-((1-carboxy
(Silethyl) thio) -2,4-difluorophenyl group, 5
-((1-carboxyethyl) thio) -4-chloro-2
-Fluorophenyl group, 5-((1-carboxyethyl
L) thio) -4-bromo-2-fluorophenyl group, 5
-((1-methoxycarbonylethyl) thio) -2,4
-Difluorophenyl group, 5-((1-methoxycarbo
Nylethyl) thio) -4-chloro-2-fluorophenyl
Group, 5-((1-methoxycarbonylethyl) thio)
-4-bromo-2-fluorophenyl group, 5-((1-
Ethoxycarbonylethyl) thio) -2,4-difluoro
Rophenyl group, 5-((1-ethoxycarbonylethyl
L) thio) -4-chloro-2-fluorophenyl group, 5
-((1-ethoxycarbonylethyl) thio) -4-bu
Lomo-2-fluorophenyl group, 5-((1-propoxy
Cicarbonylethyl) thio) -2,4-difluorophen
A 5-((1-propoxycarbonylethyl) thio group
E) -4-chloro-2-fluorophenyl group, 5-
((1-propoxycarbonylethyl) thio) -4-bu
Lomophenyl group, 5-((1-butoxycarbonylethyl
Ru) thio) -2,4-difluorophenyl group, 5-
((1-butoxycarbonylethyl) thio) -4-chloro
B-2-fluorophenyl group, 5-((1-butoxyca
Rubonylethyl) thio) -4-bromo-2-fluoroph
Enyl group, 5-((1-amyloxycarbonylethyl)
Ru) thio) -2,4-difluorophenyl group, 5-
((1-amyloxycarbonylethyl) thio) -4-
Chloro-2-fluorophenyl group, 5-((1-amyl
Oxycarbonylethyl) thio) -4-bromo-2-f
A fluorophenyl group, 5-((1-cyclohexyloxy
Carbonylethyl) thio) -2,4-difluorophenyl
Group, 5-((1-cyclohexyloxycarbonyl
Tyl) thio) -4-chloro-2-fluorophenyl group,
5-((1-cyclohexyloxycarbonylethyl)
Thio) -4-bromo-2-fluorophenyl group, 5-
((1-cyclopentyloxycarbonylethyl) thio
E) -2,4-difluorophenyl group, 5-((1-si
Clopentyloxycarbonylethyl) thio) -4-c
Rolo-2-fluorophenyl group, 5-((1-cyclope
Nthyloxycarbonylethyl) thio) -4-bromo-
2-fluorophenyl group, 5-((1-isopropoxy
Carbonylethyl) thio) -2,4-difluorophenyl
Group, 5-((1-isopropoxycarbonylethyl)
Thio) -4-chloro-2-fluorophenyl group, 5-
((1-isopropoxycarbonylethyl) thio) -4
A bromo-2-fluorophenyl group,

5-aminocarbonylmethylthio-2,4
-Difluorophenyl group, 5-aminocarbonylmethyl
Thio-4-chloro-2-fluorophenyl group, 5-amido
Nocarbonylmethylthio-4-bromo-2-fluoroph
Enyl group, 5-methylaminocarbonylmethylthio-
2,4-difluorophenyl group, 5-methylaminocar
Bonylmethylthio-4-chloro-2-fluorophenyl
Group, 5-methylaminocarbonylmethylthio-4-bro
Mo-2-fluorophenyl group, 5-dimethylaminocar
Bonylmethylthio-2,4-difluorophenyl group, 5
-Dimethylaminocarbonylmethylthio-4-chloro-
2-fluorophenyl group, 5-dimethylaminocarboni
A methylthio-4-bromo-2-fluorophenyl group,
5-diethylaminocarbonylmethylthio-2,4-di
Fluorophenyl group, 5-diethylaminocarbonyl
Tylthio-4-chloro-2-fluorophenyl group, 5-
Diethylaminocarbonylmethylthio-4-bromo-2
-Fluorophenyl group, 5-ethylmethylaminocarbo
Nylmethylthio-2,4-difluorophenyl group, 5-
Ethylmethylaminocarbonylmethylthio-4-chloro
-2-fluorophenyl group, 5-ethylmethylaminoca
Rubonylmethylthio-4-bromo-2-fluorophenyl
Group, 5-((1-aminocarbonylethyl) thio)-
2,4-difluorophenyl group, 5-((1-aminoca
Rubonylethyl) thio) -4-chloro-2-fluoroph
Enyl group, 5-((1-aminocarbonylethyl) thio
E) -4-bromo-2-fluorophenyl group, 5-
((1-methylaminocarbonylethyl) thio) -2,
4-difluorophenyl group, 5-((1-methylamino
Carbonylethyl) thio) -4-chloro-2-fluoro
Phenyl group, 5-((1-methylaminocarbonylethyl
L) thio) -4-bromo-2-fluorophenyl group, 5
-((1-dimethylaminocarbonylethyl) thio)-
2,4-difluorophenyl group, 5-((1-dimethyl
Aminocarbonylethyl) thio) -4-chloro-2-fu
A fluorophenyl group, 5-((1-dimethylaminocarbo
Nylethyl) thio) -4-bromo-2-fluorophenyl
Group, 5-((1-diethylaminocarbonylethyl)
Thio) -2,4-difluorophenyl group, 5-((1-
Diethylaminocarbonylethyl) thio) -4-chloro
-2-fluorophenyl group, 5-((1-diethylamido
Noncarbonylethyl) thio) -4-bromo-2-fluoro
Rophenyl group, 5-((1-ethylmethylaminocarbo
Nylethyl) thio) -2,4-difluorophenyl group,
5-((1-ethylmethylaminocarbonylethyl) thio
E) -4-chloro-2-fluorophenyl group, 5-
((1-ethylmethylaminocarbonylethyl) thio)
-4-bromo-2-fluorophenyl group, 5-methoxy
Sulfonyl-2,4-difluorophenyl group, 5-metho
Xisulfonyl-4-chloro-2-fluorophenyl
Group, 5-methoxysulfonyl-4-bromo-2-fluoro
Rophenyl group, 5-ethoxysulfonyl-2,4-diph
Fluorophenyl group, 5-ethoxysulfonyl-4-chloro
2-fluorophenyl group, 5-ethoxysulfonyl
-4-bromo-2-fluorophenyl group, 5-isopro
Poxysulfonyl-2,4-difluorophenyl group, 5
-Isopropoxysulfonyl-4-chloro-2-fluoro
Rophenyl group, 5-isopropoxysulfonyl-4-bu
Lomo-2-fluorophenyl group, 5-allyloxysul
Honyl-2,4-difluorophenyl group, 5-allyluo
Xisulfonyl-4-chloro-2-fluorophenyl
Group, 5-allyloxysulfonyl-4-bromo-2-f
Fluorophenyl group, 5-dimethylaminosulfonyl-
2,4-difluorophenyl group, 5-dimethylaminos
A rufonyl-4-chloro-2-fluorophenyl group, 5-
Dimethylaminosulfonyl-4-bromo-2-fluoro
Phenyl group, 5-diethylaminosulfonyl-2,4-
Difluorophenyl group, 5-diethylaminosulfonyl
-4-chloro-2-fluorophenyl group, 5-diethyl
Aminosulfonyl-4-bromo-2-fluorophenyl
Group, 5-carboxy-2,4-difluorophenyl group,
5-carboxy-4-chloro-2-fluorophenyl
Group, 5-carboxy-4-bromo-2-fluorophenyl
Group, 5-methoxycarbonyl-2,4-difluorophenyl
Enyl group, 5-methoxycarbonyl-4-chloro-2-
Fluorophenyl group, 5-methoxycarbonyl-4-bu
Lomo-2-fluorophenyl group, 5-ethoxycarboni
Ru-2,4-difluorophenyl group, 5-ethoxy
Bonyl-4-chloro-2-fluorophenyl group, 5-e
Toxicarbonyl-4-bromo-2-fluorophenyl
Group, 5-propoxycarbonyl-2,4-difluorophenyl
Enyl group, 5-propoxycarbonyl-4-chloro-2
-Fluorophenyl group, 5-propoxycarbonyl-4
-Bromo-2-fluorophenyl group, 5-butoxycal
Bonyl-2,4-difluorophenyl group, 5-butoxy
Carbonyl-4-chloro-2-fluorophenyl group, 5
-Butoxycarbonyl-4-bromo-2-fluorophene
Nyl group, 5-amyloxycarbonyl-2,4-difur
Orophenyl group, 5-amyloxycarbonyl-4-c
Loro-2-fluorophenyl group, 5-amyloxycal
Bonyl-4-bromo-2-fluorophenyl group, 5-i
Sopropoxycarbonyl-2,4-difluorophenyl
Group, 5-isopropoxycarbonyl-4-chloro-2-
Fluorophenyl group, 5-isopropoxycarbonyl-
4-bromo-2-fluorophenyl group, 5-cyclopen
Tyloxycarbonyl-2,4-difluorophenyl
Group, 5-cyclopentyloxycarbonyl-4-chloro
-2-fluorophenyl group, 5-cyclopentyloxy
Carbonyl-4-bromo-2-fluorophenyl group, 5
-Cyclohexyloxycarbonyl-2,4-difluoro
Rophenyl group, 5-cyclohexyloxycarbonyl-
4-chloro-2-fluorophenyl group, 5-cyclohexyl
Siloxycarbonyl-4-bromo-2-fluorofe
Nyl group, 5-benzyloxycarbonyl-2,4-diph
Fluorophenyl group, 5-benzyloxycarbonyl-4
-Chloro-2-fluorophenyl group, 5-benzyloxy
A cicarbonyl-4-bromo-2-fluorophenyl group,
5- (2-chloroethoxycarbonyl) -2,4-diph
Fluorophenyl group, 5- (2-chloroethoxycarboni
) -4-chloro-2-fluorophenyl group, 5- (2
-Chloroethoxycarbonyl) -4-bromo-2-fur
Orophenyl group, 5- (2-bromoethoxycarbonyl)
L) -2,4-difluorophenyl group, 5- (2-bro
Moethoxycarbonyl) -4-chloro-2-fluoroph
Enyl group, 5- (2-bromoethoxycarbonyl) -4
-Bromo-2-fluorophenyl group, 5-aminocarbo
Nyl-2,4-difluorophenyl group, 5-aminocar
Bonyl-4-chloro-2-fluorophenyl group, 5-A
Minocarbonyl-4-bromo-2-fluorophenyl
Group, 5-methylaminocarbonyl-2,4-difluoro
Phenyl group, 5-methylaminocarbonyl-4-chloro
-2-fluorophenyl group, 5-methylaminocarboni
4-bromo-2-fluorophenyl group, 5-ethyl
Aminocarbonyl-2,4-difluorophenyl group, 5
-Ethylaminocarbonyl-4-chloro-2-fluoro
Phenyl group, 5-ethylaminocarbonyl-4-bromo
-2-fluorophenyl group, 5-dimethylaminocarbo
Nyl-2,4-difluorophenyl group, 5-dimethyla
Minocarbonyl-4-chloro-2-fluorophenyl
Group, 5-dimethylaminocarbonyl-4-bromo-2-
Fluorophenyl group, 5-diethylaminocarbonyl-
2,4-difluorophenyl group, 5-diethylaminoca
Rubonyl-4-chloro-2-fluorophenyl group, 5-
Diethylaminocarbonyl-4-bromo-2-fluoro
Phenyl group, 5-ethylmethylaminocarbonyl-2,
4-difluorophenyl group, 5-ethylmethylaminoca
Rubonyl-4-chloro-2-fluorophenyl group, 5-
Ethylmethylaminocarbonyl-4-bromo-2-fur
Orophenyl group, 5-methylcarbonyl-2,4-diph
Fluorophenyl group, 5-methylcarbonyl-4-chloro
-2-fluorophenyl group, 5-methylcarbonyl-4
-Bromo-2-fluorophenyl group, 5-ethylcarbo
Nyl-2,4-difluorophenyl group, 5-ethylcar
Bonyl-4-chloro-2-fluorophenyl group, 5-e
Tylcarbonyl-4-bromo-2-fluorophenyl
Group, 5-chloromethylcarbonyl-2,4-difluoro
Phenyl group, 5-chloromethylcarbonyl-4-chloro
-2-fluorophenyl group, 5-chloromethyl carbonyl
4-bromo-2-fluorophenyl group, 5-formi
2,4-difluorophenyl group, 5-formyl-4
-Chloro-2-fluorophenyl group, 5-formyl-4
-Bromo-2-fluorophenyl group, 5- (2-carbo
(Xyethyl) -2,4-difluorophenyl group, 5-
(2-carboxyethyl) -4-chloro-2-fluoro
Phenyl group, 5- (2-carboxyethyl) -4-bro
Mo-2-fluorophenyl group, 5- (2-methoxycal
Bonylethyl) -2,4-difluorophenyl group, 5-
(2-methoxycarbonylethyl) -4-chloro-2-
Fluorophenyl group, 5- (2-methoxycarbonyl
Tyl) -4-bromo-2-fluorophenyl group, 5-
(2-ethoxycarbonylethyl) -2,4-difluoro
Rophenyl group, 5- (2-ethoxycarbonylethyl)
-4-chloro-2-fluorophenyl group, 5- (2-E
Toxycarbonylethyl) -4-bromo-2-fluoro
Phenyl group, 5- (2-chloro-2-methoxycarbonyl)
Ruethyl) -2,4-difluorophenyl group, 5- (2
-Chloro-2-methoxycarbonylethyl) -4-chloro
B-2-fluorophenyl group, 5- (2-chloro-2-
Methoxycarbonylethyl) -4-bromo-2-fluoro
Rophenyl group, 5- (2-chloro-2-ethoxycarbo)
Nylethyl) -2,4-difluorophenyl group, 5-
(2-chloro-2-ethoxycarbonylethyl) -4-
Chloro-2-fluorophenyl group, 5- (2-chloro-
2-ethoxycarbonylethyl) -4-bromo-2-f
A fluorophenyl group, 5- (2-methoxycarbonylvinyl)
Ru) -2,4-difluorophenyl group, 5- (2-meth
Xycarbonylcarbonyl) -4-chloro-2-fluorop
Enyl group, 5- (2-methoxycarbonylvinyl) -4
-Bromo-2-fluorophenyl group, 5- (2-ethoxy
(Cicarbonylvinyl) -2,4-difluorophenyl
Group, 5- (2-ethoxycarbonylvinyl) -4-chloro
2-fluorophenyl group, 5- (2-ethoxycal
Bonyl vinyl) -4-bromo-2-fluorophenyl
Group, 5-methoxycarbonylmethoxycarbonylmethoxy
C-2,4-difluorophenyl group, 5-methoxycal
Bonylmethoxycarbonylmethoxy-4-chloro-2-
Fluorophenyl group, 5-methoxycarbonylmethoxy
Carbonylmethoxy-4-bromo-2-fluorophenyl
Group, 5-ethoxycarbonylmethoxycarbonyl meth
Xy-2,4-difluorophenyl group, 5-ethoxyca
Rubonylmethoxycarbonylmethoxy-4-chloro-2
-Fluorophenyl group, 5-ethoxycarbonylmethoxy
Cicarbonylmethoxy-4-bromo-2-fluorofe
Nyl group, 5- (1- (methoxycarbonylmethoxycal
Bonyl) ethoxy) -2,4-difluorophenyl group,
5- (1- (methoxycarbonylmethoxycarbonyl)
Ethoxy) -4-chloro-2-fluorophenyl group, 5
-(1- (methoxycarbonylmethoxycarbonyl) d
Toxi) -4-bromo-2-fluorophenyl group, 5-
(1- (ethoxycarbonylmethoxycarbonyl) ethoxy
Xy) -2,4-difluorophenyl group, 5- (1-
(Ethoxycarbonylmethoxycarbonyl) ethoxy)
-4-chloro-2-fluorophenyl group, 5- (1-
(Ethoxycarbonylmethoxycarbonyl) ethoxy)
-4-bromo-2-fluorophenyl group, 5-((1-
Methoxycarbonylethoxy) carbonylmethoxy)-
2,4-difluorophenyl group, 5-((1-methoxy
Carbonylethoxy) carbonylmethoxy) -4-chloro
B-2-fluorophenyl group, 5-((1-methoxyca
Rubonylethoxy) carbonylmethoxy) -4-bromo
-2-fluorophenyl group, 5-((1-ethoxycal
Bonylethoxy) carbonylmethoxy) -2,4-diph
A fluorophenyl group, 5-((1-ethoxycarbonyl
Toxi) carbonylmethoxy) -4-chloro-2-fur
Orophenyl group, 5-((1-ethoxycarbonylethoxy
Xy) carbonylmethoxy) -4-bromo-2-fluoro
Rophenyl group, 5- (1-((1-methoxycarbonyl)
Ethoxy) carbonyl) ethoxy) -2,4-difluoro
Rophenyl group, 5- (1-((1-methoxycarbonyl)
Ethoxy) carbonyl) ethoxy) -4-chloro-2-
Fluorophenyl group, 5- (1-((1-methoxycal
Bonylethoxy) carbonyl) ethoxy) -4-bromo
-2-fluorophenyl group, 5- (1-((1-ethoxy
(Cyclocarbonylethoxy) carbonyl) ethoxy) -2,
4-difluorophenyl group, 5- (1-((1-ethoxy
Cicarbonylethoxy) carbonyl) ethoxy) -4-
Chloro-2-fluorophenyl group, 5- (1-((1-
Ethoxycarbonylethoxy) carbonyl) ethoxy)
-4-bromo-2-fluorophenyl group, 5-methoxy
Carbonylmethoxycarbonylmethylthio-2,4-di
Fluorophenyl group, 5-methoxycarbonylmethoxy
Carbonylmethylthio-4-chloro-2-fluorophene
Nyl group, 5-methoxycarbonylmethoxycarbonyl
Tylthio-4-bromo-2-fluorophenyl group, 5-
Ethoxycarbonylmethoxycarbonylmethylthio-
2,4-difluorophenyl group, 5-ethoxycarboni
Methoxycarbonylmethylthio-4-chloro-2-f
Fluorophenyl group, 5-ethoxycarbonylmethoxyca
Rubonylmethylthio-4-bromo-2-fluorophenyl
Group, 5- (1- (methoxycarbonylmethoxycarbo)
Nyl) ethylthio) -2,4-difluorophenyl group,
5- (1- (methoxycarbonylmethoxycarbonyl)
An ethylthio) -4-chloro-2-fluorophenyl group,
5- (1- (methoxycarbonylmethoxycarbonyl)
An ethylthio) -4-bromo-2-fluorophenyl group,
5- (1- (ethoxycarbonylmethoxycarbonyl)
Ethylthio) -2,4-difluorophenyl group, 5-
(1- (ethoxycarbonylmethoxycarbonyl) ethyl
Ruthio) -4-chloro-2-fluorophenyl group, 5-
(1- (ethoxycarbonylmethoxycarbonyl) ethyl
Ruthio) -4-bromo-2-fluorophenyl group, 5-
((1-methoxycarbonylethoxy) carbonylmethyl
Ruthio) -2,4-difluorophenyl group, 5-((1
-Methoxycarbonylethoxy) carbonylmethylthio
E) -4-chloro-2-fluorophenyl group, 5-
((1-methoxycarbonylethoxy) carbonylmethyl
Ruthio) -4-bromo-2-fluorophenyl group, 5-
((1-ethoxycarbonylethoxy) carbonylmethyl
Ruthio) -2,4-difluorophenyl group, 5-((1
-Ethoxycarbonylethoxy) carbonylmethylthio
E) -4-chloro-2-fluorophenyl group, 5-
((1-ethoxycarbonylethoxy) carbonylmethyl
Ruthio) -4-bromo-2-fluorophenyl group, 5-
(1-((1-methoxycarbonylethoxy) carboni
Le) ethylthio) -2,4-difluorophenyl group, 5
-(1-((1-methoxycarbonylethoxy) carbo
Nyl) ethylthio) -4-chloro-2-fluorophenyl
Group, 5- (1-((1-methoxycarbonylethoxy)
B) carbonyl) ethylthio) -4-bromo-2-fur
Orophenyl group, 5- (1-((1-ethoxycarbonyl)
Ruethoxy) carbonyl) ethylthio) -2,4-diph
A fluorophenyl group, 5- (1-((1-ethoxycarbo)
Nilethoxy) carbonyl) ethylthio) -4-chloro
-2-fluorophenyl group, 5- (1-((1-ethoxy
Cicarbonylethoxy) carbonyl) ethylthio) -4
-Bromo-2-fluorophenyl group, 5-methoxycal
Bonylmethoxycarbonyl-2,4-difluorophenyl
Group, 5-methoxycarbonylmethoxycarbonyl-4
-Chloro-2-fluorophenyl group, 5-methoxycal
Bonylmethoxycarbonyl-4-bromo-2-fluoro
Phenyl group, 5-ethoxycarbonylmethoxycarbonyl
Ru-2,4-difluorophenyl group, 5-ethoxy
Bonylmethoxycarbonyl-4-chloro-2-fluoro
Phenyl group, 5-ethoxycarbonylmethoxycarbonyl
4-bromo-2-fluorophenyl group, 5- (1-
Methoxycarbonylethoxy) carbonyl-2,4-di
Fluorophenyl group, 5- (1-methoxycarbonyl
Toxi) carbonyl-4-chloro-2-fluorophenyi
Group, 5- (1-methoxycarbonylethoxy) carbo
Nyl-4-bromo-2-fluorophenyl group, 5- (1
-Ethoxycarbonylethoxy) carbonyl-2,4-
Difluorophenyl group, 5- (1-ethoxycarbonyl)
Ethoxy) carbonyl-4-chloro-2-fluorophene
Nyl group, 5- (1-ethoxycarbonylethoxy) cal
Bonyl-4-bromo-2-fluorophenyl group, 2-
Loro-4-fluorophenyl group, 2,4-dichlorophen
Nyl group, 2-chloro-4-bromophenyl group, 5-nitro
B-2-Chloro-4-fluorophenyl group, 5-nitro
-2,4-dichlorophenyl group, 5-nitro-2-chloro
B-4-bromophenyl group, 5-amino-2-chloro-
4-fluorophenyl group, 5-amino-2,4-dichloro
Rophenyl group, 5-amino-2-chloro-4-bromop
Enyl group, 5-hydroxy-2-chloro-4-fluoro
Phenyl group, 5-hydroxy-2,4-dichlorophenyl
Group, 5-hydroxy-2-chloro-4-bromophenyi
Group, 5-mercapto-2-chloro-4-fluorophene
Nyl group, 5-mercapto-2,4-dichlorophenyl
Group, 5-mercapto-2-chloro-4-bromophenyl
Group, 5-chlorosulfonyl-2-chloro-4-fluoro
Phenyl group, 5-chlorosulfonyl-2,4-dichloro
Phenyl group, 5-chlorosulfonyl-2-chloro-4-
Bromophenyl group, 5-methylamino-2-chloro-4
-Fluorophenyl group, 5-methylamino-2,4-di
Chlorophenyl group, 5-methylamino-2-chloro-4
-Bromophenyl group, 5-ethylamino-2-chloro-
4-fluorophenyl group, 5-ethylamino-2,4-
Dichlorophenyl group, 5-ethylamino-2-chloro-
4-bromophenyl group, 5-allylamino-2-chloro
-4-fluorophenyl group, 5-allylamino-2,4
-Dichlorophenyl group, 5-allylamino-2-chloro
-4-bromophenyl group, 5-propargylamino-2
-Chloro-4-fluorophenyl group, 5-propargyl
Amino-2,4-dichlorophenyl group, 5-propargy
Rumin-2-chloro-4-bromophenyl group, 5-
(1-methyl-2-propynylamino) -2-chloro-
4-fluorophenyl group, 5- (1-methyl-2-pro
Pinylamino) -2,4-dichlorophenyl group, 5-
(1-methyl-2-propynylamino) -2-chloro-
4-bromophenyl group, 5-methanesulfonylamino-
2-chloro-4-fluorophenyl group, 5-methanesulfur
Honylamino-2,4-dichlorophenyl group, 5-meta
Sulfonylamino-2-chloro-4-bromophenyl
Group, 5-ethanesulfonylamino-2-chloro-4-f
A fluorophenyl group, 5-ethanesulfonylamino-2,
4-dichlorophenyl group, 5-ethanesulfonylamino
-2-chloro-4-bromophenyl group, 5-chlorometa
N-sulfonylamino-2-chloro-4-fluorophenyl
Group, 5-chloromethanesulfonylamino-2,4-di
Chlorophenyl group, 5-chloromethanesulfonylamino
-2-chloro-4-bromophenyl group, 5-trifluoro
Romethanesulfonylamino-2-chloro-4-fluoro
Phenyl group, 5-trifluoromethanesulfonylamino
-2,4-dichlorophenyl group, 5-trifluorometa
Sulfonylamino-2-chloro-4-bromophenyl
Group, 5- (dimethanesulfonylamino) -2-chloro-
4-fluorophenyl group, 5- (dimethanesulfonyla
Mino) -2,4-dichlorophenyl group, 5- (dimethane
Sulfonylamino) -2-chloro-4-bromophenyl
Group, 5- (methanesulfonyl (methyl) amino) -2-
Chloro-4-fluorophenyl group, 5- (methanesulfo
Nyl (methyl) amino) -2,4-dichlorophenyl
Group, 5- (methanesulfonyl (methyl) amino) -2-
Chloro-4-bromophenyl group, 5- (methanesulfoni
(Propargyl) amino) -2-chloro-4-fluoro
Rophenyl group, 5- (methanesulfonyl (propargy
L) amino) -2,4-dichlorophenyl group, 5- (meth)
Tansulfonyl (propargyl) amino) -2-chloro
-4-bromophenyl group, 5-methoxycarbonylamido
No-2-chloro-4-fluorophenyl group, 5-methoxy
Cyclocarbonylamino-2,4-dichlorophenyl group, 5
-Methoxycarbonylamino-2-chloro-4-bromo
Phenyl group, 5-ethoxycarbonylamino-2-chloro
Ro-4-fluorophenyl group, 5-ethoxycarbonyl
Amino-2,4-dichlorophenyl group, 5-ethoxyca
Rubonylamino-2-chloro-4-bromophenyl group,
5-propoxycarbonylamino-2-chloro-4-fu
A fluorophenyl group, 5-propoxycarbonylamino-
2,4-dichlorophenyl group, 5-propoxycarboni
2-amino-4-chlorophenyl group, 5-i
Sopropoxycarbonylamino-2-chloro-4-fur
Orophenyl group, 5-isopropoxycarbonylamino
-2,4-dichlorophenyl group, 5-isopropoxy
Rubonylamino-2-chloro-4-bromophenyl group,
5-butoxycarbonylamino-2-chloro-4-fur
Orophenyl group, 5-butoxycarbonylamino-2,
4-dichlorophenyl group, 5-butoxycarbonylamido
No-2-chloro-4-bromophenyl group, 5-amylio
Xycarbonylamino-2-chloro-4-fluorophene
Nyl group, 5-amyloxycarbonylamino-2,4-
Dichlorophenyl group, 5-amyloxycarbonylamido
No-2-chloro-4-bromophenyl group, 5-methoxy
Carbonylmethylamino-2-chloro-4-fluoroph
Enyl group, 5-methoxycarbonylmethylamino-2,
4-dichlorophenyl group, 5-methoxycarbonylmethyl
2-amino-4-chlorophenyl group, 5-E
Toxylcarbonylmethylamino-2-chloro-4-fur
Orophenyl group, 5-ethoxycarbonylmethylamino
-2,4-dichlorophenyl group, 5-ethoxycarboni
A methylamino-2-chloro-4-bromophenyl group,
5-propoxycarbonylmethylamino-2-chloro-
4-fluorophenyl group, 5-propoxycarbonyl
Tylamino-2,4-dichlorophenyl group, 5-propo
Xycarbonylmethylamino-2-chloro-4-bromo
Phenyl group, 5-butoxycarbonylmethylamino-2
-Chloro-4-fluorophenyl group, 5-butoxycal
Bonylmethylamino-2,4-dichlorophenyl group, 5
-Butoxycarbonylmethylamino-2-chloro-4-
Bromophenyl group, 5-amyloxycarbonylmethyl
Amino-2-chloro-4-fluorophenyl group, 5-A
Miloxycarbonylmethylamino-2,4-dichloro
Phenyl group, 5-amyloxycarbonylmethylamino
-2-chloro-4-bromophenyl group, 5-isopropo
Xycarbonylmethylamino-2-chloro-4-fluoro
Rophenyl group, 5-isopropoxycarbonylmethyla
Mino-2,4-dichlorophenyl group, 5-isopropoxy
Cicarbonylmethylamino-2-chloro-4-bromop
Enyl group, 5-cyclopentyloxycarbonylmethyl
Amino-2-chloro-4-fluorophenyl group, 5-cy
Clopentyloxycarbonylmethylamino-2,4-
Dichlorophenyl group, 5-cyclopentyloxycarbo
Nylmethylamino-2-chloro-4-bromophenyl
Group, 5-cyclohexyloxycarbonylmethylamino
-2-chloro-4-fluorophenyl group, 5-cyclo
Xyloxycarbonylmethylamino-2,4-dichloro
Rophenyl group, 5-cyclohexyloxycarbonyl
Tylamino-2-chloro-4-bromophenyl group, 5-
((1-methoxycarbonylethyl) amino) -2-c
Loro-4-fluorophenyl group, 5-((1-methoxy
Carbonylethyl) amino) -2,4-dichlorophenyl
Group, 5-((1-methoxycarbonylethyl) amido
(No) -2-chloro-4-bromophenyl group, 5-((1
-Ethoxycarbonylethyl) amino) -2-chloro-
4-fluorophenyl group, 5-((1-ethoxycarbo
Nylethyl) amino) -2,4-dichlorophenyl group,
5-((1-ethoxycarbonylethyl) amino) -2
-Chloro-4-bromophenyl group, 5-((1-propo
Xycarbonylethyl) amino) -2-chloro-4-f
A fluorophenyl group, 5-((1-propoxycarbonyl
Ethyl) amino) -2,4-dichlorophenyl group, 5-
((1-propoxycarbonylethyl) amino) -2-
Chloro-4-bromophenyl group, 5-((1-butoxy
Carbonylethyl) amino) -2-chloro-4-fluoro
Rophenyl group, 5-((1-butoxycarbonylethyl
L) amino) -2,4-dichlorophenyl group, 5-
((1-butoxycarbonylethyl) amino) -2-c
Loro-4-bromophenyl group, 5-((1-amyloxy
(Cyclocarbonylethyl) amino) -2-chloro-4-fur
Orophenyl group, 5-((1-amyloxycarbonyl
Ethyl) amino) -2,4-dichlorophenyl group, 5-
((1-amyloxycarbonylethyl) amino) -2
-Chloro-4-bromophenyl group, 5-((1-isoprop
Ropoxycarbonylethyl) amino) -2-chloro-4
-Fluorophenyl group, 5-((1-isopropoxy
Rubonylethyl) amino) -2,4-dichlorophenyl
Group, 5-((1-isopropoxycarbonylethyl) a
Mino) -2-chloro-4-bromophenyl group, 5-
((1-cyclopentyloxycarbonylethyl) amido
No) 2-chloro-4-fluorophenyl group, 5-
((1-cyclopentyloxycarbonylethyl) amido
(No) -2,4-dichlorophenyl group, 5-((1-cyclohexyl)
Lopentyloxycarbonylethyl) amino) -2-c
Rolo-4-bromophenyl group, 5-((1-cyclohexyl)
Siloxycarbonylethyl) amino) -2-chloro-
4-fluorophenyl group, 5-((1-cyclohexyl)
Oxycarbonylethyl) amino) -2,4-dichloro
Phenyl group, 5-((1-cyclohexyloxycarbo
Nylethyl) amino) -2-chloro-4-bromophenyi
Group,

5-methoxy-2-chloro-4-fluoro
Phenyl group, 5-methoxy-2,4-dichlorophenyl
Group, 5-methoxy-2-chloro-4-bromophenyl
Group, 5-ethoxy-2-chloro-4-fluorophenyl
Group, 5-ethoxy-2,4-dichlorophenyl group, 5-
Ethoxy-2-chloro-4-bromophenyl group, 5-i
A sopropoxy-2-chloro-4-fluorophenyl group,
5-isopropoxy-2,4-dichlorophenyl group, 5
-Isopropoxy-2-chloro-4-bromophenyl
Group, 5-propoxy-2-chloro-4-fluorophenyl
A 5-propoxy-2,4-dichlorophenyl group;
5-propoxy-2-chloro-4-bromophenyl group,
5- (2-chloroethoxy) -2-chloro-4-fluoro
Rophenyl group, 5- (2-chloroethoxy) -2,4-
Dichlorophenyl group, 5- (2-chloroethoxy) -2
-Chloro-4-bromophenyl group, 5- (1,1,2,2
2-tetrafluoroethoxy) -2-chloro-4-fur
Orophenyl group, 5- (1,1,2,2-tetrafluoro)
Roethoxy) -2,4-dichlorophenyl group, 5-
(1,1,2,2-tetrafluoroethoxy) -2-c
Loro-4-bromophenyl group, 5-cyclopentyloxy
C-2-chloro-4-fluorophenyl group, 5-cyclo
Pentyloxy-2,4-dichlorophenyl group, 5-cy
Clopentyloxy-2-chloro-4-bromophenyl
Group, 5-cyclohexyloxy-2-chloro-4-fur
Orophenyl group, 5-cyclohexyloxy-2,4-
Dichlorophenyl group, 5-cyclohexyloxy-2-
Chloro-4-bromophenyl group, 5-allyloxy-2
-Chloro-4-fluorophenyl group, 5-allyloxy
-2,4-dichlorophenyl group, 5-allyloxy-2
-Chloro-4-bromophenyl group, 5- (2-chloro-
2-propenyloxy) -2-chloro-4-fluoroph
Enyl group, 5- (2-chloro-2-propenyloxy)
-2,4-dichlorophenyl group, 5- (2-chloro-2
-Propenyloxy) -2-chloro-4-bromopheni
Group, 5- (2,5-dichloro-2-propenyloxy)
B) 2-chloro-4-fluorophenyl group, 5-
(2,5-dichloro-2-propenyloxy) -2,4
-Dichlorophenyl group, 5- (2,5-dichloro-2-
Propenyloxy) -2-chloro-4-bromophenyl
Group 5- (2-methyl-2-propenyloxy) -2-
Chloro-4-fluorophenyl group, 5- (2-methyl-
2-propenyloxy) -2,4-dichlorophenyl
Group 5- (2-methyl-2-propenyloxy) -2-
Chloro-4-bromophenyl group, 5- (1-methyl-2
-Propenyloxy) -2-chloro-4-fluorophene
Nyl group, 5- (1-methyl-2-propenyloxy)-
2,4-dichlorophenyl group, 5- (1-methyl-2-
Propenyloxy) -2-chloro-4-bromophenyl
Group, 5-propargyloxy-2-chloro-4-fluoro
Rophenyl group, 5-propargyloxy-2,4-dic
Lorophenyl group, 5-propargyloxy-2-chloro
-4-bromophenyl group, 5- (1-methyl-2-pro
Pinyloxy) -2-chloro-4-fluorophenyl
The group 5- (1-methyl-2-propynyloxy) -2,
4-dichlorophenyl group, 5- (1-methyl-2-pro
A pinyloxy) -2-chloro-4-bromophenyl group,
5- (5-bromo-2-propynyloxy) -2-chloro
B-4-fluorophenyl group, 5- (5-bromo-2-
Propynyloxy) -2,4-dichlorophenyl group, 5
-(5-bromo-2-propynyloxy) -2-chloro
-4-bromophenyl group, 5- (5-chloro-2-pro
Pinyloxy) -2-chloro-4-fluorophenyl
The group 5- (5-chloro-2-propynyloxy) -2,
4-dichlorophenyl group, 5- (5-chloro-2-pro
A pinyloxy) -2-chloro-4-bromophenyl group,
5-cyanomethyloxy-2-chloro-4-fluorofur
Enyl group, 5-cyanomethyloxy-2,4-dichloro
Phenyl group, 5-cyanomethyloxy-2-chloro-4
-Bromophenyl group, 5-methoxymethoxy-2-chloro
Ro-4-fluorophenyl group, 5-methoxymethoxy-
2,4-dichlorophenyl group, 5-methoxymethoxy-
2-chloro-4-bromophenyl group, 5-ethoxymeth
Xy-2-chloro-4-fluorophenyl group, 5-ethoxy
Xymethoxy-2,4-dichlorophenyl group, 5-ethoxy
Xymethoxy-2-chloro-4-bromophenyl group, 5
-Methylthiomethyloxy-2-chloro-4-fluoro
Phenyl group, 5-methylthiomethyloxy-2,4-di
Chlorophenyl group, 5-methylthiomethyloxy-2-
Chloro-4-bromophenyl group, 5-carboxymethoxy
C-2-chloro-4-fluorophenyl group, 5-carbo
Xymethoxy-2,4-dichlorophenyl group, 5-cal
Boxymethoxy-2-chloro-4-bromophenyl group,
5-methoxycarbonylmethoxy-2-chloro-4-f
Fluorophenyl group, 5-methoxycarbonylmethoxy-
2,4-dichlorophenyl group, 5-methoxycarbonyl
Methoxy-2-chloro-4-bromophenyl group, 5-e
Toxylcarbonylmethoxy-2-chloro-4-fluoro
Phenyl group, 5-ethoxycarbonylmethoxy-2,4
-Dichlorophenyl group, 5-ethoxycarbonylmethoxy
C-2-chloro-4-bromophenyl group, 5-propoxy
Cicarbonylmethoxy-2-chloro-4-fluorophene
Nyl group, 5-propoxycarbonylmethoxy-2,4-
Dichlorophenyl group, 5-propoxycarbonyl methoxy
C-2-chloro-4-bromophenyl group, 5-butoxy
Carbonylmethoxy-2-chloro-4-fluorophenyl
Group, 5-butoxycarbonylmethoxy-2,4-dic
Lorophenyl group, 5-butoxycarbonylmethoxy-2
-Chloro-4-bromophenyl group, 5-amyloxyca
Rubonylmethoxy-2-chloro-4-fluorophenyl
Group, 5-amyloxycarbonylmethoxy-2,4-di
Chlorophenyl group, 5-amyloxycarbonyl methoxy
C-2-chloro-4-bromophenyl group, 5-isopro
Poxycarbonylmethoxy-2-chloro-4-fluoro
Phenyl group, 5-isopropoxycarbonylmethoxy-
2,4-dichlorophenyl group, 5-isopropoxycal
A bonylmethoxy-2-chloro-4-bromophenyl group,
5-cyclopentyloxycarbonylmethoxy-2-c
Loro-4-fluorophenyl group, 5-cyclopentylo
Xycarbonylmethoxy-2,4-dichlorophenyl
Group, 5-cyclopentyloxycarbonylmethoxy-2
-Chloro-4-bromophenyl group, 5-cyclohexyl
Oxycarbonylmethoxy-2-chloro-4-fluoro
Phenyl group, 5-cyclohexyloxycarbonyl meth
Xy-2,4-dichlorophenyl group, 5-cyclohexyl
Leoxycarbonylmethoxy-2-chloro-4-bromo
Phenyl group, 5-((1-carboxyethyl) oxy)
-2-chloro-4-fluorophenyl group, 5-((1-
(Carboxyethyl) oxy) -2,4-dichlorophenyl
Group, 5-((1-carboxyethyl) oxy) -2-
Chloro-4-bromophenyl group, 5-((1-methoxy
Carbonylethyl) oxy) -2-chloro-4-fluoro
Rophenyl group, 5-((1-methoxycarbonylethyl)
L) oxy) -2,4-dichlorophenyl group, 5-
((1-methoxycarbonylethyl) oxy) -2-c
Loro-4-bromophenyl group, 5-((1-ethoxyca
Rubonylethyl) oxy) -2-chloro-4-fluoro
Phenyl group, 5-((1-ethoxycarbonylethyl)
Oxy) -2,4-dichlorophenyl group, 5-((1-
Ethoxycarbonylethyl) oxy) -2-chloro-4
-Bromophenyl group, 5-((1-propoxycarboni
Ruethyl) oxy) -2-chloro-4-fluorophenyl
Group, 5-((1-propoxycarbonylethyl) oxo
B) -2,4-dichlorophenyl group, 5-((1-pro
Poxycarbonylethyl) oxy) -2-chloro-4-
Bromophenyl group, 5-((1-amyloxycarboni
Ruethyl) oxy) -2-chloro-4-fluorophenyl
Group, 5-((1-amyloxycarbonylethyl) O
Xy) -2,4-dichlorophenyl group, 5-((1-A
Myloxycarbonylethyl) oxy) -2-chloro-
4-bromophenyl group, 5-((1-isopropoxy
Rubonylethyl) oxy) -2-chloro-4-fluoro
Phenyl group, 5-((1-isopropoxycarbonyl
Tyl) oxy) -2,4-dichlorophenyl group, 5-
((1-isopropoxycarbonylethyl) oxy)-
2-chloro-4-bromophenyl group, 5-((1-cyclohexyl)
Lopentyloxycarbonylethyl) oxy) -2-c
Loro-4-fluorophenyl group, 5-((1-cyclope
Ethyloxycarbonylethyl) oxy) -2,4-di
Chlorophenyl group, 5-((1-cyclopentyloxy
Carbonylethyl) oxy) -2-chloro-4-bromo
Phenyl group, 5-((1-cyclohexyloxycarbo
Nylethyl) oxy) -2-chloro-4-fluorophene
5-((1-cyclohexyloxycarbonyl)
Ethyl) oxy) -2,4-dichlorophenyl group, 5-
((1-cyclohexyloxycarbonylethyl) oxo
B) 2-chloro-4-bromophenyl group, 5-amino
Carbonylmethoxy-2-chloro-4-fluorophenyl
Group, 5-aminocarbonylmethoxy-2,4-dichloro
Rophenyl group, 5-aminocarbonylmethoxy-2-c
Rollo-4-bromophenyl group, 5-methylaminocarbo
Nilmethoxy-2-chloro-4-fluorophenyl group,
5-methylaminocarbonylmethoxy-2,4-dichloro
Rophenyl group, 5-methylaminocarbonylmethoxy-
2-chloro-4-bromophenyl group, 5-dimethylamido
Nocarbonylmethoxy-2-chloro-4-fluorophene
Nyl group, 5-dimethylaminocarbonylmethoxy-2,
4-dichlorophenyl group, 5-dimethylaminocarboni
Methoxy-2-chloro-4-bromophenyl group, 5-
Diethylaminocarbonylmethoxy-2-chloro-4-
Fluorophenyl group, 5-diethylaminocarbonyl
Toxic-2,4-dichlorophenyl group, 5-diethyla
Minocarbonylmethoxy-2-chloro-4-bromofe
Nyl group, 5-methylethylaminocarbonylmethoxy-
2-chloro-4-fluorophenyl group, 5-methylethyl
L-aminocarbonylmethoxy-2,4-dichlorophenyl
Group, 5-methylethylaminocarbonylmethoxy-2
-Chloro-4-bromophenyl group, 5-((1-amino
Carbonylethyl) oxy) -2-chloro-4-fluoro
Rophenyl group, 5-((1-aminocarbonylethyl)
Oxy) -2,4-dichlorophenyl group, 5-((1-
Aminocarbonylethyl) oxy) -2-chloro-4-
Bromophenyl group, 5-((1-methylaminocarboni
Ruethyl) oxy) -2-chloro-4-fluorophenyl
Group, 5-((1-methylaminocarbonylethyl) O
Xy) -2,4-dichlorophenyl group, 5-((1-
Tylaminocarbonylethyl) oxy) -2-chloro-
4-bromophenyl group, 5-((1-dimethylaminoca
Rubonylethyl) oxy) -2-chloro-4-fluoro
Phenyl group, 5-((1-dimethylaminocarbonyl
Tyl) oxy) -2,4-dichlorophenyl group, 5-
((1-dimethylaminocarbonylethyl) oxy)-
2-chloro-4-bromophenyl group, 5-((1-die
Tylaminocarbonylethyl) oxy) -2-chloro-
4-fluorophenyl group, 5-((1-diethylamino
Carbonylethyl) oxy) -2,4-dichlorophenyl
Group, 5-((1-diethylaminocarbonylethyl)
Oxy) -2-chloro-4-bromophenyl group, 5-
((1-ethylmethylaminocarbonylethyl) oki
B) 2-chloro-4-fluorophenyl group, 5-
((1-ethylmethylaminocarbonylethyl) oki
B) a 2,4-dichlorophenyl group, 5-((1-ethyl
Methylaminocarbonylethyl) oxy) -2-chloro
B-4-bromophenyl group, 5-dimethylaminooxy
Carbonylmethoxy-2-chloro-4-fluorophenyl
Group, 5-dimethylaminooxycarbonylmethoxy-
2,4-dichlorophenyl group, 5-dimethylaminooxy
Cicarbonylmethoxy-2-chloro-4-bromopheni
Group, 5-diethylaminooxycarbonylmethoxy-
2-chloro-4-fluorophenyl group, 5-diethyla
Minooxycarbonylmethoxy-2,4-dichlorofe
Nyl group, 5-diethylaminooxycarbonylmethoxy
-2-chloro-4-bromophenyl group, 5-methylthio
-2-chloro-4-fluorophenyl group, 5-methylthio
O-2,4-dichlorophenyl group, 5-methylthio-2
-Chloro-4-bromophenyl group, 5-ethylthio-2
-Chloro-4-fluorophenyl group, 5-ethylthio-
2,4-dichlorophenyl group, 5-ethylthio-2-c
Loro-4-bromophenyl group, 5-isopropylthio-
2-chloro-4-fluorophenyl group, 5-isopropyl
Luthio-2,4-dichlorophenyl group, 5-isopropyl
Luthio-2-chloro-4-bromophenyl group, 5- (2
-Chloroethylthio) -2-chloro-4-fluorophene
Nyl group, 5- (2-chloroethylthio) -2,4-dic
Lorophenyl group, 5- (2-chloroethylthio) -2-
Chloro-4-bromophenyl group, 5-cyclopentylchi
O-2-chloro-4-fluorophenyl group, 5-cyclo
Pentylthio-2,4-dichlorophenyl group, 5-cycl
A lopentylthio-2-chloro-4-bromophenyl group,
5-cyclohexylthio-2-chloro-4-fluoroph
Phenyl group, 5-cyclohexylthio-2,4-dichloro
Phenyl group, 5-cyclohexylthio-2-chloro-4
-Bromophenyl group, 5-allylthio-2-chloro-4
-Fluorophenyl group, 5-allylthio-2,4-dic
Lorophenyl group, 5-allylthio-2-chloro-4-bu
Lomophenyl group, 5- (2-chloro-2-propenyl)
E) -2-chloro-4-fluorophenyl group, 5- (2
-Chloro-2-propenylthio) -2,4-dichloroph
Enyl group, 5- (2-chloro-2-propenylthio)-
2-chloro-4-bromophenyl group, 5- (2,5-di
Chloro-2-propenylthio) -2-chloro-4-fur
Orophenyl group, 5- (2,5-dichloro-2-prope
Nylthio) -2,4-dichlorophenyl group, 5- (2,
5-dichloro-2-propenylthio) -2-chloro-4
-Bromophenyl group, 5- (1-methyl-2-propeni)
Ruthio) -2-chloro-4-fluorophenyl group, 5-
(1-methyl-2-propenylthio) -2,4-dichloro
Rophenyl group, 5- (1-methyl-2-propenyl)
E) -2-chloro-4-bromophenyl group, 5-propa
Lugylthio-2-chloro-4-fluorophenyl group, 5
-Propargylthio-2,4-dichlorophenyl group, 5
-Propargylthio-2-chloro-4-bromophenyl
Group 5- (1-methyl-2-propynylthio) -2-c
Loro-4-fluorophenyl group, 5- (1-methyl-2
-Propynylthio) -2,4-dichlorophenyl group, 5
-(1-methyl-2-propynylthio) -2-chloro-
4-bromophenyl group, 5-carboxymethylthio-2
-Chloro-4-fluorophenyl group, 5-carboxymethyl
Tylthio-2,4-dichlorophenyl group, 5-carboxy
Cimethylthio-2-chloro-4-bromophenyl group, 5
-Methoxycarbonylmethylthio-2-chloro-4-f
Fluorophenyl group, 5-methoxycarbonylmethylthio
-2,4-dichlorophenyl group, 5-methoxycarbonyl
Methylthio-2-chloro-4-bromophenyl group, 5
-Ethoxycarbonylmethylthio-2-chloro-4-f
Fluorophenyl group, 5-ethoxycarbonylmethylthio
-2,4-dichlorophenyl group, 5-ethoxycarboni
Methylthio-2-chloro-4-bromophenyl group, 5
-Propoxycarbonylmethylthio-2-chloro-4-
Fluorophenyl group, 5-propoxycarbonylmethyl
Thio-2,4-dichlorophenyl group, 5-propoxyca
Rubonylmethylthio-2-chloro-4-bromophenyl
Group, 5-butoxycarbonylmethylthio-2-chloro-
4-fluorophenyl group, 5-butoxycarbonylmethyl
Luthio-2,4-dichlorophenyl group, 5-butoxyca
Rubonylmethylthio-2-chloro-4-bromophenyl
Group, 5-amyloxycarbonylmethylthio-2-chloro
B-4-fluorophenyl group, 5-amyloxycarbo
Nylmethylthio-2,4-dichlorophenyl group, 5-A
Miloxycarbonylmethylthio-2-chloro-4-bu
Lomophenyl group, 5-isopropoxycarbonylmethyl
Thio-2-chloro-4-fluorophenyl group, 5-iso
Propoxycarbonylmethylthio-2,4-dichloroph
Enyl group, 5-isopropoxycarbonylmethylthio-
2-chloro-4-bromophenyl group, 5-cyclopentene
Ruoxycarbonylmethylthio-2-chloro-4-fur
Orophenyl group, 5-cyclopentyloxycarbonyl
Methylthio-2,4-dichlorophenyl group, 5-cyclo
Pentyloxycarbonylmethylthio-2-chloro-4
-Bromophenyl group, 5-cyclohexyloxycarbo
Nylmethylthio-2-chloro-4-fluorophenyl
Group, 5-cyclohexyloxycarbonylmethylthio-
2,4-dichlorophenyl group, 5-cyclohexyloxy
Cicarbonylmethylthio-2-chloro-4-bromofe
Nyl group, 5-((1-carboxyethyl) thio) -2-
Chloro-4-fluorophenyl group, 5-((1-carbo
Xylethyl) thio) -2,4-dichlorophenyl group, 5
-((1-carboxyethyl) thio) -2-chloro-4
-Bromophenyl group, 5-((1-methoxycarbonyl
Ethyl) thio) -2-chloro-4-fluorophenyl
Group, 5-((1-methoxycarbonylethyl) thio)-
2,4-dichlorophenyl group, 5-((1-methoxyca
Rubonylethyl) thio) -2-chloro-4-bromofe
A 5-((1-ethoxycarbonylethyl) thio group
E) 2-chloro-4-fluorophenyl group, 5-
((1-ethoxycarbonylethyl) thio) -2,4-
Dichlorophenyl group, 5-((1-ethoxycarbonyl
Ethyl) thio) -2-chloro-4-bromophenyl group,
5-((1-propoxycarbonylethyl) thio) -2
-Chloro-4-fluorophenyl group, 5-((1-pro
Poxycarbonylethyl) thio) -2,4-dichloroph
Enyl group, 5-((1-propoxycarbonylethyl)
Thio) -2-chloro-4-bromophenyl group, 5-
((1-butoxycarbonylethyl) thio) -2-chloro
B-4-fluorophenyl group, 5-((1-butoxyca
Rubonylethyl) thio) -2,4-dichlorophenyl
Group, 5-((1-butoxycarbonylethyl) thio)-
2-chloro-4-bromophenyl group, 5-((1-amido
Ruoxycarbonylethyl) thio) -2-chloro-4-
Fluorophenyl group, 5-((1-amyloxycarbo
Nylethyl) thio) -2,4-dichlorophenyl group, 5
-((1-amyloxycarbonylethyl) thio) -2
-Chloro-4-bromophenyl group, 5-((1-cyclo
Hexyloxycarbonylethyl) thio) -2-chloro
-4-fluorophenyl group, 5-((1-cyclohexyl
Ruoxycarbonylethyl) thio) -2,4-dichloro
Phenyl group, 5-((1-cyclohexyloxycarbo
Nylethyl) thio) -2-chloro-4-bromophenyl
Group, 5-((1-cyclopentyloxycarbonylethyl)
L) thio) -2-chloro-4-fluorophenyl group, 5
-((1-cyclopentyloxycarbonylethyl) thio
E) -2,4-dichlorophenyl group, 5-((1-cyclohexyl)
Lopentyloxycarbonylethyl) thio) -2-chloro
B-4-bromophenyl group, 5-((1-isopropoxy
(Cyclocarbonylethyl) thio) -2-chloro-4-fluoro
Rophenyl group, 5-((1-isopropoxycarbonyl
Ethyl) thio) -2,4-dichlorophenyl group, 5-
((1-isopropoxycarbonylethyl) thio) -2
-Chloro-4-bromophenyl group, 5-aminocarboni
A methylthio-2-chloro-4-fluorophenyl group,
5-aminocarbonylmethylthio-2,4-dichloroph
Enyl group, 5-aminocarbonylmethylthio-2-chloro
B-4-bromophenyl group, 5-methylaminocarboni
A methylthio-2-chloro-4-fluorophenyl group,
5-methylaminocarbonylmethylthio-2,4-dic
Lorophenyl group, 5-methylaminocarbonylmethylthio
O-2-chloro-4-bromophenyl group, 5-dimethyl
Aminocarbonylmethylthio-2-chloro-4-fluoro
Rophenyl group, 5-dimethylaminocarbonylmethylthio
O-2,4-dichlorophenyl group, 5-dimethylamino
Carbonylmethylthio-2-chloro-4-bromopheni
Group, 5-diethylaminocarbonylmethylthio-2-
Chloro-4-fluorophenyl group, 5-diethylamino
A carbonylmethylthio-2,4-dichlorophenyl group,
5-diethylaminocarbonylmethylthio-2-chloro
-4-bromophenyl group, 5-ethylmethylaminocar
Bonylmethylthio-2-chloro-4-fluorophenyl
Group, 5-ethylmethylaminocarbonylmethylthio-
2,4-dichlorophenyl group, 5-ethylmethylamino
Carbonylmethylthio-2-chloro-4-bromopheni
Group, 5-((1-aminocarbonylethyl) thio)-
2-chloro-4-fluorophenyl group, 5-((1-A
Minocarbonylethyl) thio) -2,4-dichlorofe
Nyl group, 5-((1-aminocarbonylethyl) thio)
-2-chloro-4-bromophenyl group, 5-((1-
Tylaminocarbonylethyl) thio) -2-chloro-4
-Fluorophenyl group, 5-((1-methylaminocar
Bonylethyl) thio) -2,4-dichlorophenyl group,
5-((1-methylaminocarbonylethyl) thio)-
2-chloro-4-bromophenyl group, 5-((1-dimethyl
Tylaminocarbonylethyl) thio) -2-chloro-4
-Fluorophenyl group, 5-((1-dimethylaminoca
Rubonylethyl) thio) -2,4-dichlorophenyl
Group, 5-((1-dimethylaminocarbonylethyl) thio
E) -2-chloro-4-bromophenyl group, 5-((1
-Diethylaminocarbonylethyl) thio) -2-chloro
B-4-fluorophenyl group, 5-((1-diethyl
Minocarbonylethyl) thio) -2,4-dichlorofe
5-((1-diethylaminocarbonylethyl)
L) thio) -2-chloro-4-bromophenyl group, 5-
((1-ethylmethylaminocarbonylethyl) thio)
-2-chloro-4-fluorophenyl group, 5-((1-
Ethylmethylaminocarbonylethyl) thio) -2,4
-Dichlorophenyl group, 5-((1-ethylmethylamido
Noncarbonylethyl) thio) -2-chloro-4-bromo
Phenyl group, 5-methoxysulfonyl-2-chloro-4
-Fluorophenyl group, 5-methoxysulfonyl-2,
4-dichlorophenyl group, 5-methoxysulfonyl-2
-Chloro-4-bromophenyl group, 5-ethoxysulfo
Nyl-2-chloro-4-fluorophenyl group, 5-ethoxy
Xisulfonyl-2,4-dichlorophenyl group, 5-E
Toxisulfonyl-2-chloro-4-bromophenyl
Group, 5-isopropoxysulfonyl-2-chloro-4-
Fluorophenyl group, 5-isopropoxysulfonyl-
2,4-dichlorophenyl group, 5-isopropoxysul
Honyl-2-chloro-4-bromophenyl group, 5-ali
Luoxysulfonyl-2-chloro-4-fluorophenyl
Group, 5-allyloxysulfonyl-2,4-dichloro
Phenyl group, 5-allyloxysulfonyl-2-chloro
-4-bromophenyl group, 5-dimethylaminosulfoni
2-chloro-4-fluorophenyl group, 5-dimethyl
Ruaminosulfonyl-2,4-dichlorophenyl group, 5
-Dimethylaminosulfonyl-2-chloro-4-bromo
Phenyl group, 5-diethylaminosulfonyl-2-chloro
B-4-fluorophenyl group, 5-diethylaminosul
Honyl-2,4-dichlorophenyl group, 5-diethyla
Minosulfonyl-2-chloro-4-bromophenyl group,
5-carboxy-2-chloro-4-fluorophenyl
Group, 5-carboxy-2,4-dichlorophenyl group, 5
-Carboxy-2-chloro-4-bromophenyl group, 5
-Methoxycarbonyl-2-chloro-4-fluorophene
Nyl group, 5-methoxycarbonyl-2,4-dichloroph
Enyl group, 5-methoxycarbonyl-2-chloro-4-
Bromophenyl group, 5-ethoxycarbonyl-2-chloro
Ro-4-fluorophenyl group, 5-ethoxycarbonyl
-2,4-dichlorophenyl group, 5-ethoxycarboni
2-chloro-4-bromophenyl group, 5-propoxy
A cicarbonyl-2-chloro-4-fluorophenyl group,
5-propoxycarbonyl-2,4-dichlorophenyl
Group, 5-propoxycarbonyl-2-chloro-4-bro
Mophenyl group, 5-butoxycarbonyl-2-chloro-
4-fluorophenyl group, 5-butoxycarbonyl-
2,4-dichlorophenyl group, 5-butoxycarbonyl
-2-chloro-4-bromophenyl group, 5-amyloxo
A cicarbonyl-2-chloro-4-fluorophenyl group,
5-amyloxycarbonyl-2,4-dichlorophenyl
Group, 5-amyloxycarbonyl-2-chloro-4-
Bromophenyl group, 5-isopropoxycarbonyl-2
-Chloro-4-fluorophenyl group, 5-isopropoxy
Cicarbonyl-2,4-dichlorophenyl group, 5-iso
Propoxycarbonyl-2-chloro-4-bromopheni
Group, 5-cyclopentyloxycarbonyl-2-chloro
B-4-fluorophenyl group, 5-cyclopentyloxy
Cicarbonyl-2,4-dichlorophenyl group, 5-cycl
Lopentyloxycarbonyl-2-chloro-4-bromo
Phenyl group, 5-cyclohexyloxycarbonyl-2
-Chloro-4-fluorophenyl group, 5-cyclohexyl
Luoxycarbonyl-2,4-dichlorophenyl group, 5
-Cyclohexyloxycarbonyl-2-chloro-4-
Bromophenyl group, 5-benzyloxycarbonyl-2
-Chloro-4-fluorophenyl group, 5-benzyloxy
Cicarbonyl-2,4-dichlorophenyl group, 5-ben
Ziroxycarbonyl-2-chloro-4-bromopheni
Group, 5- (2-chloroethoxycarbonyl) -2-c
Loro-4-fluorophenyl group, 5- (2-chloroeth
(Xycarbonyl) -2,4-dichlorophenyl group, 5-
(2-chloroethoxycarbonyl) -2-chloro-4-
Bromophenyl group, 5- (2-bromoethoxycarboni
L) -2-chloro-4-fluorophenyl group, 5- (2
-Bromoethoxycarbonyl) -2,4-dichlorofe
Nyl group, 5- (2-bromoethoxycarbonyl) -2-
Chloro-4-bromophenyl group, 5-aminocarbonyl
-2-chloro-4-fluorophenyl group, 5-aminoca
Rubonyl-2,4-dichlorophenyl group, 5-aminoca
Rubonyl-2-chloro-4-bromophenyl group, 5-me
Tylaminocarbonyl-2-chloro-4-fluorophene
Nyl group, 5-methylaminocarbonyl-2,4-dichloro
Rophenyl group, 5-methylaminocarbonyl-2-chloro
B-4-bromophenyl group, 5-ethylaminocarboni
2-chloro-4-fluorophenyl group, 5-ethyl
Aminocarbonyl-2,4-dichlorophenyl group, 5-
Ethylaminocarbonyl-2-chloro-4-bromofe
Nyl group, 5-dimethylaminocarbonyl-2-chloro-
4-fluorophenyl group, 5-dimethylaminocarboni
2,4-dichlorophenyl group, 5-dimethylamino
Carbonyl-2-chloro-4-bromophenyl group, 5-
Diethylaminocarbonyl-2-chloro-4-fluoro
Phenyl group, 5-diethylaminocarbonyl-2,4-
Dichlorophenyl group, 5-diethylaminocarbonyl-
2-chloro-4-bromophenyl group, 5-ethylmethyl
Aminocarbonyl-2-chloro-4-fluorophenyl
Group, 5-ethylmethylaminocarbonyl-2,4-dic
Lorophenyl group, 5-ethylmethylaminocarbonyl-
2-chloro-4-bromophenyl group, 5-methylcarbo
Nyl-2-chloro-4-fluorophenyl group, 5-methyl
Carbonyl-2,4-dichlorophenyl group, 5-methyl
Carbonyl-2-chloro-4-bromophenyl group, 5
-Ethylcarbonyl-2-chloro-4-fluorophenyl
Group, 5-ethylcarbonyl-2,4-dichlorophenyl
Group, 5-ethylcarbonyl-2-chloro-4-bromo
Phenyl group, 5-chloromethylcarbonyl-2-chloro
-4-fluorophenyl group, 5-chloromethyl carbonyl
2,4-dichlorophenyl group, 5-chloromethylca
Rubonyl-2-chloro-4-bromophenyl group,
Rumyl-2-chloro-4-fluorophenyl group,
Rumyl-2,4-dichlorophenyl group, 5-formyl-
2-chloro-4-bromophenyl group, 5- (2-carbo
A (xyethyl) -2-chloro-4-fluorophenyl group,
5- (2-carboxyethyl) -2,4-dichlorofe
Nyl group, 5- (2-carboxyethyl) -2-chloro-
4-bromophenyl group, 5- (2-methoxycarbonyl)
Ethyl) -2-chloro-4-fluorophenyl group, 5-
(2-methoxycarbonylethyl) -2,4-dichloro
Phenyl group, 5- (2-methoxycarbonylethyl)-
2-chloro-4-bromophenyl group, 5- (2-ethoxy
Cicarbonylethyl) -2-chloro-4-fluorophen
Nyl group, 5- (2-ethoxycarbonylethyl) -2,
4-dichlorophenyl group, 5- (2-ethoxycarbonyl)
Ruethyl) -2-chloro-4-bromophenyl group, 5-
(2-chloro-2-methoxycarbonylethyl) -2-
Chloro-4-fluorophenyl group, 5- (2-chloro-
2-methoxycarbonylethyl) -2,4-dichloroph
Enyl group, 5- (2-chloro-2-methoxycarbonyl)
Ethyl) -2-chloro-4-bromophenyl group, 5-
(2-chloro-2-ethoxycarbonylethyl) -2-
Chloro-4-fluorophenyl group, 5- (2-chloro-
2-ethoxycarbonylethyl) -2,4-dichloroph
Enyl group, 5- (2-chloro-2-ethoxycarbonyl)
Ethyl) -2-chloro-4-bromophenyl group, 5-
(2-methoxycarbonylvinyl) -2-chloro-4-
Fluorophenyl group, 5- (2-methoxycarbonylbi
Nyl) -2,4-dichlorophenyl group, 5- (2-meth
Xycarbonylvinyl) -2-chloro-4-bromofe
Nyl group, 5- (2-ethoxycarbonylvinyl) -2-
Chloro-4-fluorophenyl group, 5- (2-ethoxy
Carbonylvinyl) -2,4-dichlorophenyl group, 5
-(2-ethoxycarbonylvinyl) -2-chloro-4
A bromophenyl group or a compound represented by the following formulas
Any of the groups listed.

[0046]

Embedded image

[0047]

Embedded image

[0048]

Embedded image

[0049]

Embedded image

[0050]

Embedded image

[0051]

Embedded image

[0052]

Embedded image

[0053]

Embedded image

[0054]

Embedded image

[0055]

Embedded image

[0056]

Embedded image

[0057]

Embedded image

[0058]

Embedded image

[0059]

Embedded image

[0060]

Embedded image

[0061]

Embedded image

[0062]

Embedded image

[0063]

Embedded image

[0064]

Embedded image

[0065]

Embedded image

[0066]

Embedded image

[0067]

Embedded image

[0068]

Embedded image

[0069]

Embedded image

[0070]

Embedded image

[0071]

Embedded image

[0072]

Embedded image

[0073]

Embedded image

[0074]

Embedded image

[0075]

Embedded image

(2) Formula 44

Embedded image [Wherein, Ar represents the same meaning as described above. A compound represented by the formula:

(3) Formula 45

Embedded image [Wherein, Ar represents the same meaning as described above. ] The compound shown by these.

(4) Formula 46

Embedded image [Wherein, Ar represents the same meaning as described above. ] The compound shown by these.

(5) Formula 47

Embedded image [Wherein, Ar represents the same meaning as described above. ] The compound shown by these.

(6) Formula 48

Embedded image [Wherein, Ar represents the same meaning as described above. ] The compound shown by these.

(7) Formula 49

Embedded image [Wherein, Ar represents the same meaning as described above. ] The compound shown by these.

(8) Formula 50

Embedded image [Wherein, Ar represents the same meaning as described above. ] The compound shown by these.

(9) Formula 51

Embedded image [Wherein, Ar represents the same meaning as described above. ] The compound shown by these.

(10) Formula 52

Embedded image [Wherein, Ar represents the same meaning as described above. ] The compound shown by these.

Next, some of the hydrazone compounds represented by the general formula (11) are shown in Table 1 together with the compound numbers. General formula 53

Embedded image Compound represented by

[0086]

[Table 1]

Next, formulation examples are shown. Formulation Example 1 50 parts of the compound of the present invention, 3 parts of calcium ligninsulfonate, 2 parts of sodium lauryl sulfate and 45 parts of synthetic hydrous silicon oxide are thoroughly pulverized and mixed to obtain each wettable powder. Formulation Example 2 10 parts of the compound of the present invention, 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate, 35 parts of xylene and 35 parts of cyclohexanone are mixed well to obtain each emulsion. Formulation Example 3 2 parts of each of the compounds of the present invention, 2 parts of synthetic hydrous silicon oxide, 2 parts of calcium ligninsulfonate, 30 parts of bentonite and 64 parts of kaolin kure are well pulverized and mixed, and water is added and kneaded well, followed by granulation. Dry to obtain each granule. Formulation Example 4 25 parts each of the compound of the present invention, polyvinyl alcohol 10
% Aqueous solution and 25 parts of water are mixed and wet-pulverized until the average particle size becomes 5 μm or less to obtain each suspending agent. Formulation Example 5 Into 40 parts of a 10% aqueous solution of polyvinyl alcohol, 5 parts of the compound of the present invention was added, and the mixture was emulsified and dispersed with a homogenizer until the average particle size became 10 μm or less. Water is added to obtain each concentrated emulsion.

Next, Test Examples show that the compounds of the present invention are useful as active ingredients of herbicides. Test example Upland field foliage treatment test Soil was packed in a cylindrical plastic pot having a diameter of 10 cm and a depth of 10 cm, and seeds of rice millet and strawberries were sowed and grown in a greenhouse for 19 days. Thereafter, the test compound was emulsified in accordance with Formulation Example 2, and the predetermined amount was adjusted to 100 / ha.
The mixture was diluted with water containing a spreading agent equivalent to 0 liter, and the whole foliage was uniformly treated from above the plant with a sprayer. After processing, 1
They were raised in a greenhouse for 9 days and their herbicidal efficacy was investigated. As a result, 8000 g / ha of 2- (4-chloro-2-fluoro-5-isopropoxyphenyl) -6-ethoxycarbonyl-5-trifluoromethylpyridazin-3-one was obtained.
At a dose of about 70% killing activity against dog millet and strawberry.

[0089]

According to the present invention, an excellent herbicidal effect can be obtained.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat ゛ (Reference) A01N 43/84 101 A01N 43/84 101 C07D 401/04 237 C07D 401/04 237 403/04 237 403/04 237 405/04 237 405/04 237 409/04 237 409/04 237 413/04 237 413/04 237 417/04 237 417/04 237

Claims (7)

[Claims] 1. A compound represented by the general formula: [Wherein, R ¹ represents a C1-C6 alkyl group, R ² represents a hydrogen atom or a C1-C3 alkyl group, and R ³ represents a C1-C6 alkyl group.
Represents a C3 haloalkyl group, and Q represents an optionally substituted phenyl group. And a 6-alkoxycarbonylpyridazin-3-one compound represented by the formula: 2. In the above general formula 1, Q is a general formula
Chemical formula 2 Chemical formula 2[Wherein, X represents a hydrogen atom or a halogen atom, and Y represents
Halogen, nitro, cyano or trifluoro
Z represents a methyl group¹Are oxygen, sulfur, NH
Or CH_TwoZ represents a group^TwoRepresents an oxygen or sulfur atom
And n represents 0 or 1, and R^FourIs a hydrogen atom or C1
-C3 alkyl group;^FiveIs a hydrogen atom, C1-C6
Alkyl group, C1-C6 haloalkyl group, (C3-C8
Cycloalkyl) C1-C6 alkyl group, C3-C6
Lucenyl group, C3-C6 haloalkenyl group, C3-C6
Alkynyl group, C3-C6 haloalkynyl group, cyano C
1-C6 alkyl group, C1-C4 alkoxy C1-C4
Alkyl group, C1-C3 alkoxy C1-C3 alkoxy
C1-C3 alkyl group, carboxy C1-C6 alkyl
Group, (C1-C6 alkoxy) carbonyl C1-C6
Alkyl group, {(C1-C4 alkoxy) C1-C4
Alkoxy dicarbonyl C1-C6 alkyl group, (C3-
C8 cycloalkoxy) carbonyl C1-C6 alkyl
Group, -CH_TwoCON (R¹²) R¹³Group, -CH_TwoCOON
(R¹²) R¹³Group, -CH (C1-C4 alkyl) CON
(R¹²) R¹³Group, -CH (C1-C4 alkyl) COO
N (R¹²) R¹³Group (where R¹²And R¹³May be the same
Is different from a hydrogen atom, a C1-C6 alkyl group, a C3-C
8 cycloalkyl group, C1-C6 haloalkyl group, C3
-C6 alkenyl group, C3-C6 alkynyl group, cyano
C1-C6 alkyl group, C1-C4 alkoxy C1-C
4-alkyl group, C1-C4 alkylthio C1-C4 alkyl
Kill group, carboxy C1-C6 alkyl group, (C1-C
6 alkoxy) carbonyl C1-C6 alkyl group, (C
3-C8 cycloalkoxy) carbonyl C1-C6 al
A kill group, (C1-C6 alkyl) carbonyloxy C2
-C6 alkyl group, (C1-C6 alkyl) carbonyl
Amino C2-C6 alkyl group, hydroxy C2-C6
Alkyl group, benzyl group which may be substituted,
Phenyl group or ｛(C1-C4 alkoxy)
B) C1-C4 alkyl @ carbonyl C1-C6 alkyl
Or R¹²And R¹³And trimethylene,
Tetramethylene, pentamethylene, ethyleneoxyethyl
Represents len or ethylenethioethylene. ), C1-C
4-alkylthio C1-C4 alkyl group or hydroxy
Represents a C1-C6 alkyl group,⁶Is C1-C6 alk
Group, C1-C6 haloalkyl group, cyano group, formyl
Group, carboxyl group, hydroxy C1-C6 alkyl
Group, C1-C6 alkoxy C1-C6 alkyl group, C1
-C4 alkylthio C1-C4 alkyl group, C1-C6
Alkoxy C1-C6 alkoxy C1-C6 alkyl
Group, (C1-C6 alkyl) carbonyloxy C1-C
6 alkyl group, (C1-C6 haloalkyl) carbonyl
An oxy C1-C6 alkyl group or (C1-C6 alcohol
Xy) a carbonyl group;⁷Is a hydrogen atom or C1
-C6 alkyl group;⁸Is C1-C6 alkyl
Group, C1-C6 haloalkyl group, hydroxy C1-C6
Alkyl group, C1-C4 alkoxy C1-C4 alkyl
Group, C1-C3 alkoxy C1-C3 alkoxy C1-
C3 alkyl group, (C1-C6 alkyl) carbonylo
Xy C1-C6 alkyl group, (C1-C6 haloalkyl
Ru) carbonyl C1-C6 alkyl group, carboxy group,
A carboxy C1-C6 alkyl group, (C1-C8 alcohol
Xy) carbonyl group, (C1-C6 haloalkoxy)
Rubonyl group, (C3-C10 cycloalkoxy) carbo
Nyl group, (C3-C8 alkenyloxy) carbonyl
A (C3-C8 alkynyloxy) carbonyl group,
(C1-C6 alkyl) aminocarbonyl group, di (C1
—C6 alkyl) aminocarbonyl group, (C1-C6
Alkyl) aminocarbonyloxy C1-C6 alkyl group
Or di (C1-C6 alkyl) aminocarbonyloxy
C represents a C1-C6 alkyl group, B represents a hydrogen atom,
Atom, nitro group, cyano group, chlorosulfonyl group, O
R ^TenGroup, SR^TenGroup, SO_TwoOR^{twenty one}Group, N (R¹²) R
¹³Group, SO_TwoN (R¹²) R¹³Group, NR¹²(COR⁹) Group,
NR¹²(SO_TwoR²⁸) Group, N (SO_TwoR²⁸) (SO
_TwoR²⁹) Group, N (SO_TwoR²⁸) (COR⁹) Group, NHCO
OR¹¹Group, CONR¹²R¹³Group, CSNR¹²R¹³Group, CO
R³⁰Group, CR^{twenty three}= CR^{twenty four}COR³⁰Group, CR^{twenty three}= CR^{twenty four}C
ON (R¹²) R¹³Group, CH_TwoCHWCON (R¹²) R¹³
Group, CR³⁰= NOR³¹Group, CR³⁰= NN (R¹²) R
¹³Group, CR³⁰(Z^TwoR³²)_TwoGroup, COOR^{twenty two}Group, CH_TwoO
R^TenGroup, CR^{twenty three}= CR^{twenty four}COOR^{twenty five}Group or CH_TwoCH
WCOOR^{twenty five}Represents a group. Ｒ where R¹², R¹³And Z^Two
Represents the same meaning as described above, and W represents a hydrogen atom, a chlorine atom or
Represents a bromine atom;⁹Is a C1-C6 alkyl group, C1
-C6 haloalkyl group, C3-C8 cycloalkyl group
Or a C3-C6 alkenyl group;¹¹Is C1-C6
Alkyl group, C3-C8 cycloalkyl group or C3-
Represents a C6 alkenyl group,^{twenty one}Is C1-C6 alkyl
Group, C1-C6 haloalkyl group, C3-C8 cycloal
Kill group, C3-C6 alkenyl group, C3-C6 haloal
Kenyl group, C3-C6 alkynyl group, C3-C6 haloa
Represents a rukinyl group or a benzyl group;^{twenty two}Is a hydrogen atom,
C1-C6 alkyl group, C1-C6 haloalkyl group, C
3-C8 cycloalkyl group, benzyl group, C3-C6
Lucenyl group, C3-C6 haloalkenyl group, C3-C6
Alkynyl group, C3-C6 haloalkynyl group, cyano C
1-C6 alkyl group, C1-C4 alkoxy C1-C4
Alkyl group, C1-C4 alkylthio C1-C4 alkyl
A carboxy C1-C6 alkyl group, (C1-C8
An (alkoxy) carbonyl C1-C6 alkyl group, (C1
-C6 haloalkoxy) carbonyl C1-C6 alkyl
Group, ｛(C1-C4 alkoxy) C1-C4 alkoxy
Dicarbonyl C1-C6 alkyl group, (C3-C8
Chloroalkoxy) carbonyl C1-C6 alkyl group,
(C1-C6 alkyl) carbonyl C1-C6 alkyl
Group, (C1-C6 haloalkyl) carbonyl C1-C6
Alkyl group, {(C1-C4 alkoxy) C1-C4
Alkyl} carbonyl C1-C6 alkyl group, (C3-C
8 cycloalkyl) carbonyl C1-C6 alkyl group,
-CH_TwoCOON (R²⁶) R²⁷Group, -CH (C1-C4
Alkyl) COON (R²⁶) R²⁷Group, -CH_TwoCON
(R²⁶) R²⁷Group, -CH (C1-C4 alkyl) CON
(R²⁶) R²⁷Group (where R²⁶And R²⁷Are the same or the same
Differently, a hydrogen atom, a C1-C6 alkyl group,
Loalkyl group, C3-C6 alkenyl group, C3-C6
Rukinyl group, cyano C1-C6 alkyl group, C1-C4
Alkoxy C1-C4 alkyl group, C1-C4 alkyl
Thio C1-C4 alkyl group, carboxy C1-C6 alkyl
Kill group, (C1-C6 alkoxy) carbonyl C1-C
6 alkyl groups, (C3-C8 cycloalkoxy) carbo
A C1-C6 alkyl group or ｛(C1-C4 alkyl
Coxy) C1-C4 alkyl @ carbonyl C1-C6
Or R²⁶And R²⁷And with tetramethi
Len, pentamethylene or ethyleneoxyethylene
Represent. ), {(C1-C6 alkoxy) carbonyl C1
-C6 alkyl} oxycarbonyl C1-C6 alkyl
Or a hydroxy C2-C6 alkyl group;^{twenty three}
And R^{twenty four}Are the same or different, hydrogen atom, halogen atom
Or a C1-C6 alkyl group;^{twenty five}Is hydrogen field
Child, C1-C6 alkyl group, C1-C6 haloalkyl
A C3-C8 cycloalkyl group or a C3-C6 alkyl group
Represents a phenyl group;²⁸And R²⁹Are the same or different C
A 1-C6 alkyl group, a C1-C6 haloalkyl group,
May be substituted with a methyl group or a nitro group
Represents a phenyl group;³⁰Is a hydrogen atom, C1-C6 alkyl
, A C2-C6 alkenyl group or a C2-C6 alkyl
Represents a phenyl group;³¹Is a hydrogen atom, C1-C6 alkyl
Group, C1-C6 haloalkyl group, C3-C6 alkenyl
Group, C3-C6 haloalkenyl group, C3-C6 alkynyl
, A cyano C1-C6 alkyl group, a C1-C4 alcohol
Xy C1-C4 alkyl group, C1-C4 alkylthio C
1-C4 alkyl group, carboxy C1-C6 alkyl
Group, (C1-C6 alkoxy) carbonyl C1-C6
Alkyl group, (C3-C8 cycloalkoxy) carbonyl
A C1-C6 alkyl group or {(C1-C4 alkoxy)
B) C1-C4 alkoxy @ carbonyl C1-C6 al
Represents a kill group;³²Is a C1-C6 alkyl group or C3
-C6 represents an alkenyl group. R^TenIs a hydrogen atom, C1-C
6 alkyl groups, C1-C6 haloalkyl groups, C3-C8
Cycloalkyl group, benzyl group, C3-C6 alkenyl
Group, C3-C6 haloalkenyl group, C3-C6 alkynyl
, A C3-C6 haloalkynyl group, a cyano C1-C6
Alkyl group, C1-C4 alkoxy C1-C4 alkyl
A C1-C4 alkylthio C1-C4 alkyl group,
Ruboxy C1-C6 alkyl group, (C1-C8 alkoxy
B) a carbonyl C1-C6 alkyl group;
Loalkoxy) carbonyl C1-C6 alkyl group,
{(C1-C4 alkoxy) C1-C4 alkoxy}
Rubonyl C1-C6 alkyl group, (C3-C8 cycloa
(Ruoxy) carbonyl C1-C6 alkyl group, (C3-
C8 cycloalkyl) C1-C6 alkoxycarbonyl
C1-C6 alkyl group, -CH_TwoCOON (R¹²) R¹³
Group, -CH (C1-C4 alkyl) COON (R¹²) R
¹³Group, -CH_TwoCON (R¹²) R¹³Group, -CH (C1-
C4 alkyl) CON (R¹²) R¹³Group (where R¹²When
R¹³Has the same meaning as described above. ), C2-C6 alkenyl
Roxycarbonyl C1-C6 alkyl group, C3-C6
Haloalkenyloxycarbonyl C1-C6 alkyl
The group C3-C6 alkynyloxycarbonyl C1-C6
Alkyl group, C3-C6 haloalkynyloxycarbonyl
C1-C6 alkyl group, (C1-C6 alkylthio)
Carbonyl C1-C6 alkyl group, (C1-C6 haloa
Alkylthio) carbonyl C1-C6 alkyl group, (C3
-C6 alkenylthio) carbonyl C1-C6 alkyl
Group, (C3-C6 haloalkenylthio) carbonyl C1
-C6 alkyl group, (C3-C6 alkynylthio) carb
Bonyl C1-C6 alkyl group, (C3-C6 haloalkyl
Nylthio) carbonyl C1-C6 alkyl group, (C3-
C8 cycloalkylthio) carbonyl C1-C6 alkyl
Group, (C3-C8 cyclohaloalkylthio) carboni
C1-C6 alkyl group, {(C3-C8 cycloalkyl)
C) C1-C6 alkylthio dicarbonyl C1-C6
Alkyl group, di (C1-C6 alkyl) C = NO carbonyl
C1-C6 alkyl group, (optionally substituted
(Dithio) carbonyl C1-C6 alkyl group, (substituted
Phenylthio) carbonyl C1-C6
Alkyl group, hydroxy C2-C6 alkoxycarbonyl
C1-C6 alkyl group, (C1-C6 alkyl) carbo
Nyloxy C2-C6 alkoxycarbonyl C1-C6
Alkyl group, (C1-C6 alkyl) carbonylamino
C2-C6 alkoxycarbonyl C1-C6 alkyl
Group, {(C1-C6 alkoxy) carbonyl C1-C6
Alkyl dioxycarbonyl C1-C6 alkyl group,
Droxy C2-C6 alkyl group, C1-C6 alkoxy
Carbonyl group, C1-C6 haloalkoxycarbonyl
Group, C3-C8 cycloalkoxycarbonyl group, C3-
C6 alkenyloxycarbonyl group, even when substituted
Good benzyloxycarbonyl group, C1-C6 alkyl
Carbonyl group, C3-C6 alkenylcarbonyl group,
Optionally substituted benzyloxycarbonyl C1-C
6 alkyl groups, optionally substituted phenoxycarbo
An aryl C1-C6 alkyl group, an optionally substituted
Roxycarbonyl C1-C6 alkyl group, substituted
Optionally furyl C1-C6 alkyloxycarbonyl
C1-C6 alkyl group, thienyl which may be substituted
Oxycarbonyl C1-C6 alkyl group, substituted
Optionally thienyl C1-C6 alkyloxycarbonyl
C1-C6 alkyl group, optionally substituted pyrrolyl
Oxycarbonyl C1-C6 alkyl group, substituted
Pyrrolyloxy C1-C6 alkyloxycal
A bonyl C1-C6 alkyl group, an optionally substituted
Midazoyloxycarbonyl C1-C6 alkyl group, position
Optionally substituted imidazoyl C1-C6 alkylo
An oxycarbonyl C1-C6 alkyl group, substituted
Pyrazoyloxycarbonyl C1-C6 alkyl
Group, optionally substituted pyrazoyl C1-C6 alkyl
Roxycarbonyl C1-C6 alkyl group, substituted
Thiazoyloxycarbonyl C1-C6 alkyl
A killing group, an optionally substituted thiazoyl C1-C6
Alkyloxycarbonyl C1-C6 alkyl group, substituted
Oxazoyloxycarbonyl C1-C optionally
6 alkyl groups, optionally substituted oxazoyl C1
-C6 alkyloxycarbonyl C1-C6 alkyl
Group, optionally substituted isothiazoyloxycarbo
N-C 1 -C 6 alkyl group, optionally substituted iso
Thiazoyl C1-C6 alkyloxycarbonyl C1-
C6 alkyl group, optionally substituted isoxazoyl
Oxycarbonyl C1-C6 alkyl group, substituted
Isoxazoyl C1-C6 alkyloxycal
A bonyl C1-C6 alkyl group, an optionally substituted
Lysyloxycarbonyl C1-C6 alkyl group, substituted
Optionally substituted pyridyl C1-C6 alkyloxycal
A bonyl C1-C6 alkyl group, an optionally substituted
Radinyloxycarbonyl C1-C6 alkyl group, substituted
Optionally substituted pyrazinyl C1-C6 alkyloxy
Carbonyl C1-C6 alkyl group, which may be substituted
Pyrimidinyloxycarbonyl C1-C6 alkyl
Group, optionally substituted pyrimidinyl C1-C6 al
A alkyloxycarbonyl C1-C6 alkyl group, substituted
Optionally pyridazinyloxycarbonyl C1-C6
Alkyl group, optionally substituted pyridazinyl C1-
A C6 alkyloxycarbonyl C1-C6 alkyl group,
Optionally substituted indolizinyloxycarbonyl
C1-C6 alkyl group, optionally substituted indoli
Dinyl C1-C6 alkyloxycarbonyl C1-C6
Alkyl group, optionally substituted indolyloxyca
Rubonyl C1-C6 alkyl group, which may be substituted
Indolyl C1-C6 alkyloxycarbonyl C1-
C6 alkyl group, optionally substituted indazolyl
An oxycarbonyl C1-C6 alkyl group, substituted
Indazolyl C1-C6 alkyloxycarboni
C1-C6 alkyl group, quinolin which may be substituted
Roxycarbonyl C1-C6 alkyl group, substituted
Optionally quinolyl C1-C6 alkyloxycarboni
A C1-C6 alkyl group, an optionally substituted
A noryloxycarbonyl C1-C6 alkyl group, or
Optionally substituted isoquinolyl C1-C6 alkyl
Represents an oxycarbonyl C1-C6 alkyl group, or
Formula 3<Where R¹⁴Represents a hydrogen atom or a C1-C5 alkyl group
Represents, R^FifteenIs a hydrogen atom, a hydroxyl group or -OC
OR¹⁶A group represented by the formula (R¹⁶Is a C1-C6 alkyl group,
A C1-C6 haloalkyl group, a C3-C6 alkenyl group,
A C3-C8 cycloalkyl group, an optionally substituted
Enyl group, benzyl group which may be substituted or C1
-C6 represents an alkoxy group. ). Group shown by〉
Or the general formula:<Where R¹⁷Is a hydrogen atom, a halogen atom or C1-C
6 represents an alkyl group; ¹⁸Is C3-C8 cycloalkyl
C2 -C having a group, a benzyl group and an epoxy group on the carbon chain
10 alkyl groups, C3-C8 cycloalkyl C1-C6
Alkyl group, C3-C8 cycloalkyl C2-C6 alkyl
Kenyl group, the same carbon atom is OR¹⁹Group and OR²⁰Base
A substituted C1-C6 alkyl group, wherein the same carbon atom is OR
¹⁹Group and OR²⁰-C6 alkenyl substituted with a group
Group, the same carbon atom is SR¹⁹Group and SR²⁰Substituted with a group
C1-C6 alkyl group, the same carbon atom is SR¹⁹Basis
And SR ²⁰C2-C6 alkenyl group substituted with a group (here
And R¹⁹And R²⁰Are the same or different C1-C6 alkyl
Or a C1-C6 haloalkyl group,¹⁹And R²⁰
And ethylene optionally substituted with a halogen atom,
Trimethylene, ha which may be substituted with a halogen atom;
Tetramethylene, ha
Pentamethylene which may be substituted with a
Is ethyleneoxy optionally substituted with a halogen atom
Represents ethylene. ), Carboxy C2-C6 alkenyl
Group, (C1-C8 alkoxy) carbonyl C2-C6
Lucenyl group, (C1-C8 haloalkoxy) carbonyl
C2-C6 alkenyl group, ｛(C1-C4 alkoxy)
C1-C4 alkoxy @ carbonyl C2-C6 alkenyl
Or a (C3-C8 cycloalkoxy) carbonyl
Represents a C2-C6 alkenyl group. >. }]
Q-1, Q-2, Q-3, Q-4 or Q-5
The 6-alkoxycarbonyl according to claim 1, which is any one of the following.
Pyridazin-3-one compounds. 3. The 6-alkoxycarbonylpyridazin-3-one compound according to claim 2, wherein, in the general formula 1, Q is Q-1. 4. In the above general formula 1, Q is Q-1, where B is a hydrogen atom, an OR ¹⁰ group or an SR ¹⁰ group (where R ¹⁰ has the same meaning as described above). The 6-alkoxycarbonylpyridazine-3 according to claim 3, which is
-One compounds. 5. In the above general formula 1, Q is Q-1, wherein Y is a halogen atom, B is a hydrogen atom, a C1-C6 alkoxy group, a C3-C6 alkenyloxy group, a C3- C6 alkynyloxy group, C1-C6 alkoxycarbonyl group, carboxy group or (C1-C
The 6-alkoxycarbonylpyridazin-3-one compound according to claim 2, 3 or 4, which is an (8 alkoxy) carbonyl C1-C6 alkoxy group. 6. The 6-alkoxycarbonylpyridazin-3-one compound according to claim 1, wherein R ³ is a trifluoromethyl group in the general formula (1). 7. A herbicide comprising the 6-alkoxycarbonylpyridazin-3-one compound according to claim 1 as an active ingredient.