JP2001316375A - 6-hydroxy-5,6-dihydrouracil compound - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a compound having excellent herbicidal effectiveness. SOLUTION: A 5,6-dihydrouracil compound represented by general formula (I) [wherein R1 is a 1-2C haloalkyl group; and Q is a group such as Q1 represented by general formula (II) (wherein R3 is H or a halogen atom; R15 is a 3-6C alkynyl group or the like; Z is O, S or NH group; and T is a single bond or methylene group)], and a herbicide comprising the compound as an active component are provided.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a 5,6-dihydrouracil compound, a method for producing the same, and a herbicide containing the compound as an active ingredient.

[0002]

2. Description of the Related Art At present, many herbicides are commercially available and used. However, since weeds to be controlled are of many types and are long-term, they have a higher herbicidal effect and a broader herbicidal spectrum. However, there is a need for herbicides that do not cause phytotoxicity problems for crops. JP-A-06-092943
No. 4,927,451, it is described that certain 5,6-dihydrouracil compounds have herbicidal activity. However, the compounds described in those patents do not always have sufficient performance as herbicides.

[0003]

An object of the present invention is to provide a compound having excellent performance as a herbicide.

[0004]

Means for Solving the Problems The present inventors have conducted intensive studies to find a compound having excellent performance as a herbicide. As a result, the 5,6-dihydrouracil compound represented by the following general formula [I] was obtained. The present inventors have found that the composition has excellent performance as an agent, and have reached the present invention. That is, the present invention provides a compound represented by the general formula [I]: [Wherein, R ¹ represents a C1-C2 haloalkyl group, and Q represents any one of Q1 to Q3 represented by the following general formula. Wherein, R ³ represents a hydrogen atom or a halogen atom, R ⁴
Represents a hydrogen atom, a halogen atom, a cyano group, a nitro group or an ethynyl group, or has the general formula R ⁵ represents a hydrogen atom, a C1-C6 alkyl group, a halogen atom, a cyano group, a nitro group, or a hydroxyl group, and R ⁶ represents a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group. A C3-C8 cycloalkyl C1-C3 alkyl group, a C3-C6 alkenyl group, a C3-C6 alkynyl group, a cyano C1-C3 alkyl group, a C1-C3 alkoxy C1-C3 alkyl group,
C1-C3 alkylthio C1-C3 alkyl group, C1-
A C6 alkylcarbonyl group, a C1-C6 haloalkylcarbonyl group, a C3-C8 cycloalkylcarbonyl group,
Carboxy C1-C3 alkyl group, C1-C6 alkoxycarbonyl C1-C3 alkyl group, C1-C6 haloalkoxycarbonyl C1-C3 alkyl group, C3-C8
Cycloalkoxycarbonyl C1-C3 alkyl group, C
3-6 alkenyloxycarbonyl C1-C3 alkyl group, C3-C6 alkynyloxycarbonyl C1-C3
Alkyl group, C1-C3 alkoxy C1-C3 alkoxycarbonyl C1-C3 alkyl group, carboxy C1-
C3 alkoxycarbonyl C1-C3 alkyl group, C1
-C6 alkoxycarbonyl C1-C3 alkoxycarbonyl C1-C3 alkyl group, C1-C6 haloalkoxycarbonyl C1-C3 alkoxycarbonyl C1-C
3 alkyl groups, C3-C6 alkenyloxycarbonyl C1-C3 alkoxycarbonyl C1-C3 alkyl groups, C3-C6 alkynyloxycarbonyl C1-C3
Alkoxycarbonyl C1-C3 alkyl group, C3-C
8 cycloalkoxycarbonyl C1-C3 alkoxycarbonyl C1-C3 alkyl group, optionally substituted aryloxycarbonyl C1-C3 alkyl group, optionally substituted aryl C1-C3 alkoxycarbonyl C1-C3 alkyl group or C1- or represents C6 alkoxycarbonyl group or the general formula -SO ₂ R ^{17,,
-C (R 28) R 29 CON} (R 21) R 22, -C (R 30) R
^{31 COON (R 23) R 24} , Or R ⁷ represents a hydrogen atom, a C1-6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a hydroxy group, a C1-C6 alkoxy group, a C
1-C6 haloalkoxy group, C3-C8 cycloalkoxy group, C3-C6 alkenyloxy group, C3-C6 alkynyloxy group, C1-C3 alkoxy C1-C3 alkoxy group, carboxy C1-C3 alkoxy group, C1-
C6 alkoxycarbonyl C1-C3 alkoxy group, C
3-C8 cycloalkoxycarbonyl C1-C3 alkoxy group, C3-C6 alkenyloxycarbonyl C1-
C3 alkoxy, C3-C6 alkynyloxycarbonyl C1-C3 alkoxy group, or represents an optionally substituted phenoxy group or an optionally substituted benzyloxy group, or the general formula -N (R ²¹⁾ R ²² group Or —ON (R ²³ ) R ²⁴ , wherein R ⁸ is a hydroxy group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, a C3-C6
Alkenyloxy group, C3-C6 alkynyloxy group,
Represents a C1-C3 alkoxy C1-C3 alkoxy group, an optionally substituted phenoxy group or an optionally substituted benzyloxy group, or a compound represented by the general formula -N (R
²¹⁾ R ²² group or -ON (R ²³⁾ represents a group represented by R ^24, R ⁹ represents a hydrogen atom or a halogen atom, R ¹⁰ is hydroxy group, C1-C6 alkoxy group, C1-C6 haloalkoxy group , A C3-C8 cycloalkoxy group, C3
-C6 alkenyloxy group, C3-C6 alkynyloxy group, C1-C3 alkoxy C1-C3 alkoxy group,
Represents an optionally substituted phenoxy group or an optionally substituted benzyloxy group;
N (R ²¹ ) R ²² or —ON (R ²³ ) R ²⁴ represents a group represented by R ¹¹ represents a hydrogen atom or a halogen atom;
¹² is a hydrogen atom, formyl group, cyano group, nitro group, amino group, C1-C6 alkyl group, C1-C6 haloalkyl group, hydroxy C1-C3 alkyl group, C1-C3 alkoxy C1-C3 alkyl group, C1-C6 alkyl Carbonyloxy C1-C3 alkyl group, C1-C6 haloalkylcarbonyloxy C1-C3 alkyl group, carboxy group, C1-C6 alkoxycarbonyl group, C1-C
6 haloalkoxycarbonyl group, C3-C8 cycloalkoxy group, C3-C6 alkenyloxycarbonyl group, a C3-C6 alkynyloxy group or a C1-C3 alkoxy C1-C3 alkoxycarbonyl group, R ¹³ is a hydrogen atom or a C1 represents an -C3 alkyl group, R ¹⁴ is a hydrogen atom, C1-C6 alkyl group,
C1-C6 haloalkyl group, hydroxy C1-C3 alkyl group, C1-C3 alkoxy C1-C3 alkyl group,
C1-C6 alkylcarbonyloxy C1-C3 alkyl group, C1-C6 haloalkylcarbonyloxy C1-
C3 alkyl group, carboxy group, C1-C6 alkoxycarbonyl group, C1-C6 haloalkoxycarbonyl group, C3-C8 cycloalkoxycarbonyl group, C3-
C6 alkenyloxycarbonyl group, C3-C6 alkynyloxycarbonyl group or C1-C3 alkoxy C
Represents a 1-C3 alkoxycarbonyl group, wherein R ¹⁵ is C1-
C6 alkyl group, C1-C6 haloalkyl group, C3-C
8-cycloalkyl group, C3-C8 cycloalkyl C1-
C3 alkyl group, C3-C6 alkenyl group, C3-C6
Alkynyl group, cyano C1-C3 alkyl group, C1-C
3 alkoxy C1-C3 alkyl group, C1-C3 alkylthio C1-C3 alkyl group, C1-C6 alkylcarbonyl group, C1-C6 haloalkylcarbonyl group, C3
-C8 cycloalkylcarbonyl group, carboxy C1-
C3 alkyl group, C1-C6 alkoxycarbonyl C1
-C3 alkyl group, C1-C6 haloalkoxycarbonyl C1-C3 alkyl group, C3-C8 cycloalkoxycarbonyl C1-C3 alkyl group, C3-6 alkenyloxycarbonyl C1-C3 alkyl group, C3-C6 alkynyloxycarbonyl C1-C3 Alkyl group, C1
-C3 alkoxy C1-C3 alkoxycarbonyl C1
-C3 alkyl group, carboxy C1-C3 alkoxycarbonyl C1-C3 alkyl group, C1-C6 alkoxycarbonyl C1-C3 alkoxycarbonyl C1-C3
Alkyl group, C1-C6 haloalkoxycarbonyl C1
-C3 alkoxycarbonyl C1-C3 alkyl group, C
3-C8 cycloalkoxycarbonyl C1-C3 alkoxycarbonyl C1-C3 alkyl group, C3-C6 alkenyloxycarbonyl C1-C3 alkoxycarbonyl C1-C3 alkyl group, C3-C6 alkynyloxycarbonyl C1-C3 alkoxycarbonyl C1-C3
Alkyl group, optionally substituted aryloxycarbonyl C1-C3 alkyl group, optionally substituted aryl C1-C3 alkyloxycarbonyl C1-C3
Represents an alkyl group or a C1-C6 alkoxycarbonyl group, or a compound represented by the general formula And Z represents an oxygen atom, a sulfur atom or N
H represents a group, and T represents a direct bond or a methylene group. <Here, R ¹⁷ is a C1-C3 alkyl group or a C1-C3
Represents a 3 haloalkyl group, R ¹⁸ is a hydrogen atom, C1-C3
Represents an alkyl group or a C1-C6 alkoxycarbonyl group, and R ¹⁹ is a hydrogen atom, a halogen atom, a nitro group, a hydroxy group, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy. Group, C3-C8 cycloalkoxy group, C3-C6
Alkenyloxy group, C3-C6 alkynyloxy group,
Carboxy C1-C3 alkoxy group, C1-C6 alkoxycarbonyl C1-C3 alkoxy group, C3-C8 cycloalkoxycarbonyl C1-C3 alkoxy group, C
3-C6 alkenyloxycarbonyl C1-C3 alkoxy group or C3-C6 alkynyloxycarbonyl C
Represents a 1-C3 alkoxy group, and R ²⁰ represents a hydrogen atom, a halogen atom, a nitro group, a hydroxy group, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3- C8 cycloalkoxy group, C3-C6 alkenyloxy group, C3-C
6 alkynyloxy group, carboxy C1-C3 alkoxy group, C1-C6 alkoxycarbonyl C1-C3 alkoxy group, C3-C8 cycloalkoxycarbonyl C1
-C3 alkoxy group, C3-C6 alkenyloxycarbonyl C1-C3 alkoxy group or C3-C6 alkynyloxycarbonyl C1-C3 alkoxy group,
R ²¹ and R ²² independently represent a hydrogen atom or a C1-C3 alkyl group, or are bonded at the terminal to form a C2-C5
Alkylene group or C1-C3 alkyleneoxy C1-
R ²³ and R ²⁴ independently represent a hydrogen atom or a C1-C3 alkyl group, or are bonded at the terminal to form a C2-C5 alkylene group or a C1-C3 alkylene group;
3 alkyleneoxy C1-C3 alkylene group;
²⁵ is a hydrogen atom, a C1-C3 alkyl group or a C1-C6
R ²⁶ represents a hydrogen atom, a halogen atom, a nitro group, a hydroxy group, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkyl group; An alkoxy group, a C3-C6 alkenyloxy group, a C3-
C6 alkynyloxy group, carboxy C1-C3 alkoxy group, C1-C6 alkoxycarbonyl C1-C3 alkoxy group, C3-C8 cycloalkoxycarbonyl C
Represents a 1-C3 alkoxy group, a C3-C6 alkenyloxycarbonyl C1-C3 alkoxy group or a C3-C6 alkynyloxycarbonyl C1-C3 alkoxy group, and R ²⁷ represents a hydrogen atom, a halogen atom, a nitro group, a hydroxy group, a C1-C6 Alkyl group, C1-C6 haloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group, C3-C6 alkenyloxy group, C3-C6 alkynyloxy group, carboxy C1-C3 alkoxy group, C1-C6 alkoxycarbonyl C1-C3 alkoxy group, C3-C8 cycloalkoxycarbonyl C1-C3 alkoxy group, C3
-C6 alkenyloxycarbonyl C1-C3 alkoxy group or C3-C6 alkynyloxycarbonyl C1
R ²⁸ represents a hydrogen atom or C1
R ²⁹ represents a hydrogen atom or C1-
Represents a C3 alkyl group, and R ³⁰ is a hydrogen atom or C1-C
R ³¹ represents a hydrogen atom or C1-C3
R ³² , R ³³ and R ³⁴ are the same or different and each represent a hydrogen atom, a halogen atom, C1-C3
Alkyl group, C1-C3 haloalkyl group, nitro group, amino group, OH group, SH group, cyano group, carboxy group, C
1-C6 alkoxycarbonyl group, C3-C8 cycloalkoxycarbonyl group, C3-C6 alkenyloxycarbonyl group, C3-C6 alkynyloxycarbonyl group, carboxy C1-C3 alkyl group, C1-C6 alkoxycarbonyl C1-C3 alkyl group, C3 -C8 cycloalkoxycarbonyl C1-C3 alkyl group, C3
-C6 alkenyloxycarbonyl C1-C3 alkyl group, C3-C6 alkynyloxycarbonyl C1-C3
Alkyl group, carboxy C1-C3 alkoxy group, C1
-C6 alkoxycarbonyl C1-C3 alkoxy group,
C3-C8 cycloalkoxycarbonyl C1-C3 alkoxy group, C3-C6 alkenyloxycarbonyl C1
-C3 alkoxy group, C3-C6 alkynyloxycarbonyl C1-C3 alkoxy group, carboxy C1-C3
Alkylthio group, C1-C6 alkoxycarbonyl C1
-C3 alkylthio group, C3-C8 cycloalkoxycarbonyl C1-C3 alkylthio group, C3-C6 alkenyloxycarbonyl C1-C3 alkylthio group, C
3-C6 alkynyloxycarbonyl C1-C3 alkylthio group, carboxy C1-C3 alkylamino group, C
1-C6 alkoxycarbonyl C1-C3 alkylamino group, C3-C8 cycloalkoxycarbonyl C1-
A C3 alkylamino group, a C3-C6 alkenyloxycarbonyl C1-C3 alkylamino group, a C3-C6 alkynyloxycarbonyl C1-C3 alkylamino group,
C1-C6 alkoxy group, C3-C6 alkenyloxy group, C3-C6 alkynyloxy group, C1-C6 alkylcarbonyloxy group, C1-C6 alkoxycarbonyloxy group, C1-C6 alkylthio group, C3-C6 alkenylthio group, C3 -C6 alkynylthio group, C1-
C6 alkylcarbonylthio group, C1-C6 alkoxycarbonylthio group, C1-C6 alkylamino group, C3
-C6 alkenylamino group, C3-C6 alkynylamino group, C1-C6 alkylcarbonylamino group or C
Represents a 1-C6 alkoxycarbonylamino group. 〉]]
And a herbicide containing the compound as an active ingredient.

[0005]

DETAILED DESCRIPTION OF THE INVENTION In the present invention, the C1-C2 haloalkyl group represented by R ^1, a trifluoromethyl group, chlorodifluoromethyl group, difluoromethyl group, pentafluoroethyl group and the like, with R ³ The halogen atom shown represents a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and the halogen atom represented by R ⁴ represents a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and represented by R ⁵ Examples of the C1-C6 alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group (representing "iso"), a butyl group, an iso-butyl group,
a c- (representing "secondary") butyl group, a t- (representing "tertiary") butyl group and the like, and the halogen atom represents a fluorine atom, a chlorine atom, a bromine atom or an iodine atom;

The C1-C6 alkyl group represented by R ⁶ includes a methyl group, an ethyl group, a propyl group, an iso-propyl group, a butyl group, an iso-butyl group, a sec-butyl group, a t-butyl group and a pentyl group. And a hexyl group, and the like, and examples of the C1-C6 haloalkyl group include a trifluoromethyl group, a difluoromethyl group, a 2-fluoroethyl group, a 2-chloroethyl group, and a 2-bromoethyl group. Examples of the group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and the like.
Examples of the 1-C3 alkyl group include a cyclopropylmethyl group, a cyclobutylmethyl group, a cyclopentylmethyl group,
Examples of the cyclohexylmethyl group include C3-C6 alkenyl groups such as allyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, and 1,1-dimethyl-2-propenyl. And a C3-C6 alkynyl group such as a propargyl group and a 1-methyl-2- group.
Propynyl group, 2-butynyl group, 1,1-dimethyl-2
-Propynyl group and the like, and as the cyano C1-C3 alkyl group, a cyanomethyl group, a 1-cyanoethyl group,
Examples thereof include a 2-cyanoethyl group and a 1-methyl-2-cyanoethyl group. Examples of the C1-C3 alkoxyalkyl group include a methoxymethyl group, a 2-methoxyethyl group, an ethoxymethyl group, and a 2-ethoxyethyl group. , C1
Examples of the -C3 alkylthio C1-C3 alkyl group include a methylthiomethyl group, a 2-ethylthioethyl group, and a 2-methylthioethyl group. Examples of the C1-C6 alkylcarbonyl group include an acetyl group, an ethylcarbonyl group,
A propylcarbonyl group, an iso-propylcarbonyl group, a pivaloyl group and the like; and the C1-C6 haloalkylcarbonyl group include a trifluoroacetyl group, a difluoroacetyl group, a trichloroacetyl group, a dichloroacetyl group and the like; Examples of the cycloalkylcarbonyl group include a cyclopropylcarbonyl group, a cyclopentylcarbonyl group, and a cyclohexylcarbonyl group. Examples of the carboxy C1-C3 alkyl group include a carboxymethyl group, a 1-carboxyethyl group,
1-methyl-1-carboxyethyl group, 1-carboxypropyl group, 2-carboxyethyl group, 1-methyl-2
-Carbonylethyl group and the like. Examples of the C1-C6 alkoxycarbonyl C1-C3 alkyl group include a methoxycarbonylmethyl group, an ethoxycarbonylmethyl group,
Propyloxycarbonylmethyl group, iso-propyloxycarbonylmethyl group, butyloxycarbonylmethyl group, iso-butyloxycarbonylmethyl group, s
ec-butyloxycarbonylmethyl group, t-butyloxycarbonylmethyl group, pentyloxycarbonylmethyl group, iso-pentyloxycarbonylmethyl group,
Hexyloxycarbonylmethyl group, iso-hexyloxycarbonylmethyl group, 1-methoxycarbonylethyl group, 1-ethoxycarbonylethyl group, 1- (propyloxycarbonyl) ethyl group, 1- (iso-propyloxycarbonyl) ethyl group, 1- (butyloxycarbonyl) ethyl group, 1- (iso-butyloxycarbonyl) ethyl group, 1- (sec-butyloxycarbonyl) ethyl group, 1- (t-butyloxycarbonyl) ethyl group, 1- (pentyl) An oxycarbonyl) ethyl group, a 1- (iso-pentyloxycarbonyl) ethyl group, a 1- (hexyloxycarbonyl) ethyl group,
-(Iso-hexyloxycarbonyl) ethyl group, 1
-Methyl-1- (methoxycarbonyl) ethyl group, 1-
Methyl-1- (ethoxycarbonyl) ethyl group, 1-methyl-1- (propyloxycarbonyl) ethyl group, 1
-Methyl-1- (iso-propyloxycarbonyl)
Ethyl group, 1-methyl-1- (butyloxycarbonyl) ethyl group, 1-methyl-1- (iso-butyloxycarbonyl) ethyl group, 1-methyl-1- (sec-
Butyloxycarbonyl) ethyl group, 1-methyl-1-
(T-butyloxycarbonyl) ethyl group, 1-methyl-1- (pentyloxycarbonyl) ethyl group, 1-methyl-1- (iso-pentyloxycarbonyl) ethyl group, 1-methyl-1- (hexyloxycarbonyl) )
An ethyl group, a 1-methyl-1- (iso-hexyloxycarbonyl) ethyl group, and the like.

C1-C6 haloalkoxycarbonyl C1
As the -C3 alkyl group, 2-fluoroethoxycarbonylmethyl group, 2-chloroethoxycarbonylmethyl group, 2-bromoethoxycarbonylmethyl group, 2,2,2
2-trifluoroethoxycarbonylmethyl group, 2-chloroethoxycarbonylmethyl group, 2-bromoethoxycarbonylmethyl group, 1- (2-fluoroethoxycarbonyl) ethyl group, 1- (2-chloroethoxycarbonyl) ethyl group, 1 -(2-bromoethoxycarbonyl)
Ethyl group, 1- (2,2,2-trifluoroethoxycarbonyl) ethyl group, 1- (2-chloroethoxycarbonyl) ethyl group, 1- (2-bromoethoxycarbonyl) ethyl group, 1-methyl-1- (2-fluoroethoxycarbonyl) ethyl group, 1-methyl-1- (2-chloroethoxycarbonyl) ethyl group, 1-methyl-1-
(2-bromoethoxycarbonyl) ethyl group, 1-methyl-1- (2,2,2-trifluoroethoxycarbonyl) ethyl group, 1-methyl-1- (2-chloroethoxycarbonyl) ethyl group, 1-methyl -1- (2-bromoethoxycarbonyl) ethyl group and the like, and C3-C
Examples of 8-cycloalkoxycarbonyl C1-C3 alkyl groups include cyclopropyloxycarbonylmethyl, cyclobutyloxycarbonylmethyl, cyclopentyloxycarbonylmethyl, cyclohexyloxycarbonylmethyl, 1-cyclopropyloxycarbonylethyl, 1-cyclo Butyloxycarbonylethyl group, 1-cyclopentyloxycarbonylethyl group, 1
-Cyclohexyloxycarbonylethyl group, 1-methyl-1- (cyclopropyloxycarbonyl) ethyl group, 1-methyl-1- (cyclobutyloxycarbonyl) ethyl group, 1-methyl-1- (cyclopentyloxycarbonyl) ethyl group , 1-methyl-1- (cyclohexyloxycarbonyl) ethyl group and the like, and C3
Examples of the -C6 alkenyloxycarbonyl C1-C3 alkyl group include an allyloxycarbonylmethyl group, a 1-methyl-2-propenyloxycarbonylmethyl group,
A methyl-2-propenyloxycarbonylmethyl group,
1,1-dimethyl-2-propenyloxycarbonylmethyl group, 1- (allyloxycarbonyl) ethyl group,
-(1-methyl-2-propenyloxycarbonyl) ethyl group, 1- (2-methyl-2-propenyloxycarbonyl) ethyl group, 1- (1,1-dimethyl-2-propenyloxycarbonyl) ethyl group, 1 -Methyl-1-
(Allyloxycarbonyl) ethyl group, 1-methyl-1
-(1-methyl-2-propenyloxycarbonyl) ethyl group, 1-methyl-1- (2-methyl-2-propenyloxycarbonyl) ethyl group, 1-methyl-1-
(1,1-dimethyl-2-propenyloxycarbonyl) ethyl group and the like. Examples of the C3-C6 alkynyloxycarbonyl C1-C3 alkyl group include a propargyloxycarbonylmethyl group and a 1-methyl-2-propynyloxycarbonylmethyl group. Group, 2-butynyloxycarbonylmethyl group, 1,1-dimethyl-2-propynyloxycarbonylmethyl group, 1- (propargyloxycarbonyl) ethyl group, 1- (1-methyl-2-propynyloxycarbonyl) ethyl group A 1- (2-butynyloxycarbonyl) ethyl group, a 1- (1,1-dimethyl-2-propynyloxycarbonyl) ethyl group,
Methyl-1- (propargyloxycarbonyl) ethyl group, 1-methyl-1- (1-methyl-2-propynyloxycarbonyl) ethyl group, 1-methyl-1- (2-butynyloxycarbonyl) ethyl group, 1 -Methyl-1-
(1,1-dimethyl-2-propynyloxycarbonyl) ethyl group and the like, and C1-C3 alkoxy C1
As the -C3 alkoxycarbonyl C1-C3 alkyl group, a methoxymethoxycarbonylmethyl group, a 2-methoxyethoxycarbonylmethyl group, an ethoxymethoxycarbonylmethyl group, a 2-ethoxyethoxycarbonylmethyl group, a 1- (methoxymethoxycarbonyl) ethyl group, 1- (2-methoxyethoxycarbonyl) ethyl group, 1- (ethoxymethoxycarbonyl) ethyl group, 1
-(2-ethoxyethoxycarbonyl) ethyl group, 1-
Methyl-1- (methoxymethoxycarbonyl) ethyl group, 1-methyl-1- (2-methoxyethoxycarbonyl) ethyl group, 1-methyl-1- (ethoxymethoxycarbonyl) ethyl group, 1-methyl-1- (2 -Ethoxyethoxycarbonyl) ethyl group and the like;

The carboxy C1-C3 alkoxycarbonyl C1-C3 alkyl group includes carboxymethoxycarbonylmethyl, 1- (carboxy) ethoxycarbonylmethyl, 1- (carboxymethoxycarbonyl) ethyl, 1- {1- (carboxy) ) Ethoxycarbonyl @ ethyl group, 1-methyl-1- (carboxy) ethoxycarbonylmethyl group, 1- {1-methyl-1-
(Carboxy) ethoxycarbonyldiethyl group and the like. Examples of the C1-C6 alkoxycarbonyl C1-C3 alkoxycarbonyl C1-C3 alkyl group include a methoxycarbonylmethoxycarbonylmethyl group, a 1- (methoxycarbonyl) ethoxycarbonylmethyl group, −
(Methoxycarbonylmethoxycarbonyl) ethyl group,
1- {1- (methoxycarbonyl) ethoxycarbonyl} ethyl group, 1-methyl-1- (methoxycarbonyl) ethoxycarbonylmethyl group, 1- {1-methyl-
1- (methoxycarbonyl) ethoxycarbonyl} ethyl group, ethoxycarbonylmethoxycarbonylmethyl group, 1- (ethoxycarbonyl) ethoxycarbonylmethyl group, 1- (ethoxycarbonylmethoxycarbonyl) ethyl group, 1- {1- (ethoxycarbonyl) Ethoxycarbonyl @ ethyl group, 1-methyl-1- (ethoxycarbonyl) ethoxycarbonylmethyl group, 1- {1
-Methyl-1- (ethoxycarbonyl) ethoxycarbonyldiethyl group and the like, and C1-C6 haloalkoxycarbonyl C1-C3 alkoxycarbonyl C1-C
Examples of the 3 alkyl group include a 2-fluoroethoxycarbonylmethoxycarbonylmethyl group, a 1- (2-fluoroethoxycarbonyl) ethoxycarbonylmethyl group,
(2-fluoroethoxycarbonylmethoxycarbonyl) ethyl group, 1- {1- (2-fluoroethoxycarbonyl) ethoxycarbonyl} ethyl group, 1-methyl-
1- (2-fluoroethoxycarbonyl) ethoxycarbonylmethyl group, 1- {1-methyl-1- (2-fluoroethoxycarbonyl) ethoxycarbonyl} ethyl group, 2-chloroethoxycarbonylmethoxycarbonylmethyl group, 1- (2 -Chloroethoxycarbonyl) ethoxycarbonylmethyl group, 1- (2-chloroethoxycarbonylmethoxycarbonyl) ethyl group, 1- {1-
(2-chloroethoxycarbonyl) ethoxycarbonyl} ethyl group, 1-methyl-1- (2-chloroethoxycarbonyl) ethoxycarbonylmethyl group, 1- {1-
Methyl-1- (2-chloroethoxycarbonyl) ethoxycarbonyldiethyl group and the like, and examples of the C3-C6 alkenyloxycarbonyl C1-C3 alkoxycarbonyl C1-C3 alkyl group include an allyloxycarbonylmethoxycarbonylmethyl group, (Allyloxycarbonyl) ethoxycarbonylmethyl group, 1- (allyloxycarbonylmethoxycarbonyl) ethyl group, 1
-{1- (allyloxycarbonyl) ethoxycarbonyl} ethyl group, 1-methyl-1- (allyloxycarbonyl) ethoxycarbonylmethyl group, 1- {1-methyl-1- (allyloxycarbonyl) ethoxycarbonyl} ethyl group Etc. are given,

C3-C6 alkynyloxycarbonyl C
Examples of the 1-C3 alkoxycarbonyl C1-C3 alkyl group include a propargyloxycarbonylmethoxycarbonylmethyl group and a 1- (propargyloxycarbonyl)
Ethoxycarbonylmethyl group, 1- (propargyloxycarbonylmethoxycarbonyl) ethyl group, 1- {1
-(Propargyloxycarbonyl) ethoxycarbonyl} ethyl group, 1-methyl-1- (propargyloxycarbonyl) ethoxycarbonylmethyl group, 1- {1-
Methyl-1- (propargyloxycarbonyl) ethoxycarbonyldiethyl group and the like. Examples of the C3-C8 cycloalkoxycarbonyl C1-C3 alkoxycarbonyl C1-C3 alkyl group include cyclopentyloxycarbonylmethoxycarbonylmethyl group and 1- (cyclopentyl). An (oxycarbonyl) ethoxycarbonylmethyl group, a 1- (cyclopentyloxycarbonylmethoxycarbonyl) ethyl group, a 1- {1- (cyclopentyloxycarbonyl) ethoxycarbonyl} ethyl group,
Methyl-1- (cyclopentyloxycarbonyl) ethoxycarbonylmethyl group, 1- {1-methyl-1- (cyclopentyloxycarbonyl) ethoxycarbonyl}
And an optionally substituted aryloxycarbonyl C1-C3 alkyl group such as a phenoxycarbonylmethyl group, a 1-phenoxycarbonylethyl group, or a 1-methyl-1- (phenoxycarbonyl) group.
Examples of the aryl C1-C3 alkoxycarbonyl C1-C3 alkyl group which may be substituted include a benzyloxycarbonylmethyl group, a 1-benzyloxycarbonylethyl group, and a 1-methyl-1-methyl group.
(Benzyloxycarbonyl) ethyl, phenethyloxycarbonylmethyl, 1-phenethyloxycarbonylethyl, 1-methyl-1- (phenethyloxycarbonyl) ethyl and the like. Carbonyl group, ethoxycarbonyl group, propyloxycarbonyl group, is
o-propyloxycarbonyl group and the like,

[0010] The C1-C6 alkyl group represented by R ^7, methyl group, ethyl group, propyl group, iso- propyl, butyl, iso- butyl group, sec- butyl group, t- butyl group, a pentyl group And a hexyl group, and the like, and examples of the C1-C6 haloalkyl group include a trifluoromethyl group, a difluoromethyl group, a 2-fluoroethyl group, a 2-chloroethyl group, and a 2-bromoethyl group. Examples of the group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group. Examples of the C1-C6 alkoxy group include a methoxy group, an ethoxy group, a propyloxy group,
Examples thereof include a so-propyloxy group, a butyloxy group, an iso-butyloxy group, a sec-butyloxy group, a t-butyloxy group, a pentyloxy group, and a hexyloxy group. As the C1-C6 haloalkoxy group, a 2-fluoroethoxy group is exemplified. , A 2-chloroethoxy group, a 2-bromoethoxy group, and the like. Examples of the C3-C8 cycloalkoxy group include a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, a cyclohexyloxy group, and the like. Examples of the C6 alkenyloxy group include an allyloxy group, a 1-methyl-2-propenyloxy group, a 2-methyl-2-propenyloxy group, and a 1,1-
And a dimethyl-2-propenyloxy group.
Examples of the -C6 alkynyloxy group include a propargyloxy group, a 1-methyl-2-propynyloxy group, a 2-butynyloxy group, a 1,1-dimethyl-2-propynyloxy group and the like, and a C1-C3 alkoxy C1-C3 Examples of the alkoxy group include a methoxymethoxy group, a 2-methoxyethoxy group, and an ethoxymethoxy group. Examples of the carboxy C1-C3 alkoxy group include a carboxymethoxy group, a 1-carboxyethoxy group, and a 1-methyl-1 group.
-(Carboxy) ethoxy group and the like, and C1-C6
Examples of the alkoxycarbonyl C1-C3 alkoxy group include a methoxycarbonylmethoxy group, an ethoxycarbonylmethoxy group, a propyloxycarbonylmethoxy group,
iso-propyloxycarbonylmethoxy group, butyloxycarbonylmethoxy group, iso-butyloxycarbonylmethoxy group, sec-butyloxycarbonylmethoxy group, t-butyloxycarbonylmethoxy group,
Pentyloxycarbonylmethoxy group, iso-pentyloxycarbonylmethoxy group, hexyloxycarbonylmethoxy group, iso-hexyloxycarbonylmethoxy group, 1-methoxycarbonylethoxy group, 1-ethoxycarbonylethoxy group, 1- (propyloxycarbonyl) ethoxy Group, 1- (iso-propyloxycarbonyl) ethoxy group, 1- (butyloxycarbonyl) ethoxy group, 1- (iso-butyloxycarbonyl) ethoxy group, 1- (sec-butyloxycarbonyl) ethoxy group, 1- (T-butyloxycarbonyl)
Ethoxy group, 1- (pentyloxycarbonyl) ethoxy group, 1- (iso-pentyloxycarbonyl) ethoxy group, 1- (hexyloxycarbonyl) ethoxy group, 1- (iso-hexyloxycarbonyl) ethoxy group, 1-methyl -1- (methoxycarbonyl) ethoxy group, 1-methyl-1- (ethoxycarbonyl) ethoxy group, 1-methyl-1- (propyloxycarbonyl)
An ethoxy group, a 1-methyl-1- (iso-propyloxycarbonyl) ethoxy group, a 1-methyl-1- (butyloxycarbonyl) ethoxy group, a 1-methyl-1- (i
(so-butyloxycarbonyl) ethoxy group, 1-methyl-1- (sec-butyloxycarbonyl) ethoxy group, 1-methyl-1- (t-butyloxycarbonyl)
Ethoxy group, 1-methyl-1- (pentyloxycarbonyl) ethoxy group, 1-methyl-1- (iso-pentyloxycarbonyl) ethoxy group, 1-methyl-1-
(Hexyloxycarbonyl) ethoxy group, 1-methyl-1- (iso-hexyloxycarbonyl) ethoxy group and the like.

C3-C8 cycloalkoxycarbonyl C
Examples of the 1-C3 alkoxy group include a cyclopropyloxycarbonylmethoxy group, a cyclobutyloxycarbonylmethoxy group, a cyclopentyloxycarbonylmethoxy group, a cyclohexyloxycarbonylmethoxy group,
Cyclopropyloxycarbonylethoxy, 1-cyclobutyloxycarbonylethoxy, 1-cyclopentyloxycarbonylethoxy, 1-cyclohexyloxycarbonylethoxy, 1-methyl-1- (cyclopropyloxycarbonyl) ethoxy, 1-methyl -1- (cyclobutyloxycarbonyl) ethoxy group,
1-methyl-1- (cyclopentyloxycarbonyl)
Examples thereof include an ethoxy group and a 1-methyl-1- (cyclohexyloxycarbonyl) ethoxy group. Examples of the C3-C6 alkenyloxycarbonyl C1-C3 alkoxy group include an allyloxycarbonylmethoxy group and a 1-methyl-
2-propenyloxycarbonylmethoxy group, 2-methyl-2-propenyloxycarbonylmethoxy group, 1,
1-dimethyl-2-propenyloxycarbonylmethoxy group, 1- (allyloxycarbonyl) ethoxy group, 1
-(1-methyl-2-propenyloxycarbonyl) ethoxy group, 1- (2-methyl-2-propenyloxycarbonyl) ethoxy group, 1- (1,1-dimethyl-2-)
Propenyloxycarbonyl) ethoxy group, 1-methyl-1- (allyloxycarbonyl) ethoxy group, 1-methyl-1- (1-methyl-2-propenyloxycarbonyl) ethoxy group, 1-methyl-1- (2- Methyl-2
-Propenyloxycarbonyl) ethoxy group, 1-methyl-1- (1,1-dimethyl-2-propenyloxycarbonyl) ethoxy group, and the like. Examples of the C3-C6 alkynyloxycarbonyl C1-C3 alkoxy group include propargyloxy. Carbonylmethoxy group, 1-methyl-2-propynyloxycarbonylmethoxy group, 2
-Butynyloxycarbonylmethoxy group, 1,1-dimethyl-2-propynyloxycarbonylmethoxy group, 1
-(Propargyloxycarbonyl) ethoxy group, 1-
(1-methyl-2-propynyloxycarbonyl) ethoxy group, 1- (2-butynyloxycarbonyl) ethoxy group, 1- (1,1-dimethyl-2-propynyloxycarbonyl) ethoxy group, 1-methyl-1 -(Propargyloxycarbonyl) ethoxy group, 1-methyl-1-
(1-methyl-2-propynyloxycarbonyl) ethoxy group, 1-methyl-1- (2-butynyloxycarbonyl) ethoxy group, 1-methyl-1- (1,1-dimethyl-2-propynyloxycarbonyl) An ethoxy group and the like are mentioned, and the phenoxy group which may be substituted include a phenoxy group and the like, and the benzyloxy group which may be substituted include a benzyloxy group and the like.

The C1-C6 alkoxy group represented by R ⁸ includes a methoxy group, an ethoxy group, a propyloxy group,
iso-propyloxy group, butyloxy group, iso-
Examples thereof include a butyloxy group, a sec-butyloxy group, a t-butyloxy group, a pentyloxy group, and a hexyloxy group. Examples of the C1-C6 haloalkoxy group include a 2-fluoroethoxy group, a 2-chloroethoxy group and a 2-bromoethoxy group. And the like. Examples of the C3-C8 cycloalkoxy group include a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, and a cyclohexyloxy group. Examples of the C3-C6 alkenyloxy group include an allyloxy group and a -Methyl-2-propenyloxy group, 2-methyl-2-propenyloxy group, 1,1
-Dimethyl-2-propenyloxy group and the like;
Examples of the 3-C6 alkynyloxy group include a propargyloxy group, a 1-methyl-2-propynyloxy group, a 2-butynyloxy group, and a 1,1-dimethyl-2-propynyloxy group. C3
Examples of the alkoxy group include a methoxymethoxy group, a 2-methoxyethoxy group, and an ethoxymethoxy group. Examples of the optionally substituted phenoxy group include a phenoxy group and the like, and an optionally substituted benzyloxy group. Examples include a benzyloxy group and the like,

Halogen atoms represented by R ⁹ represents a chlorine atom, a bromine atom, the C1-C6 alkoxy group represented by R ^10, a methoxy group, an ethoxy group, propyloxy group, iso- propyloxy, butyloxy Group,
iso-butyloxy group, sec-butyloxy group, t
-Butyloxy group, pentyloxy group, hexyloxy group and the like. Examples of the C1-C6 haloalkoxy group include a 2-fluoroethoxy group, a 2-chloroethoxy group,
2-bromoethoxy group and the like; C3-C8 cycloalkoxy group includes cyclopropyloxy group, cyclobutyloxy group, cyclopentyloxy group and cyclohexyloxy group; and C3-C6 alkenyloxy group includes Allyloxy group, 1-methyl-2-propenyloxy group, 2-methyl-2-propenyloxy group, 1,1-dimethyl-2-propenyloxy group, and the like, and examples of the C3-C6 alkynyloxy group include: A propargyloxy group, a 1-methyl-2-propynyloxy group, a 2-butynyloxy group, a 1,1-dimethyl-2-propynyloxy group, and the like. Examples of the C1-C3 alkoxy C1-C3 alkoxy group include a methoxymethoxy group. , 2-methoxyethoxy group, ethoxymethoxy group and the like, As good phenoxy group can have, a phenoxy group and the like, as good a benzyloxy group which may be substituted, a benzyl group and the like,

[0014] Halogen atoms represented by R ¹¹ represents a chlorine atom, a bromine atom, the C1-C6 alkyl group represented by R ^12, a methyl group, an ethyl group, etc. iso- propyl group and the like, C1- As the C6 haloalkyl group,
Chloromethyl group, bromomethyl group, fluoromethyl group,
Dichloromethyl group, dibromomethyl group, difluoromethyl group and the like, and the hydroxy C1-C3 alkyl group includes a hydroxymethyl group and a 2-hydroxyethyl group; and the C1-C3 alkoxy C1-C3 alkyl group includes , Methoxymethyl group, ethoxymethyl group,
an iso-propyloxymethyl group and the like;
Examples of the C6 alkylcarbonyloxy C1-C3 alkyl group include a methylcarbonyloxymethyl group and an ethylcarbonyloxymethyl group. Examples of the C1-C6 haloalkylcarbonyloxy C1-C3 alkyl group include a trifluoromethylcarbonyloxymethyl group, Examples of the C1-C6 alkoxycarbonyl group include a methoxycarbonyl group, an ethoxycarbonyl group, a propyloxycarbonyl group, an iso-propyloxycarbonyl group, a butyloxycarbonyl group, and an iso-butyloxycarbonyl group. Group, sec-butyloxycarbonyl group, t
-Butyloxycarbonyl group, pentyloxycarbonyl group, hexyloxycarbonyl group and the like;
As the -C6 haloalkoxycarbonyl group, 2,2,2
2-trifluoroethoxycarbonyl group, 2-fluoroethoxycarbonyl group, 2-chloroethoxycarbonyl group, 2-bromoethoxycarbonyl group and the like;
Examples of the 3-C8 cycloalkoxycarbonyl group include a cyclopropyloxycarbonyl group, a cyclobutyloxycarbonyl group, a cyclopentyloxycarbonyl group, a cyclohexyloxycarbonyl group, and the like.
6-alkenyloxycarbonyl groups include allyloxycarbonyl groups and the like, C3-C6 alkynyloxycarbonyl groups include propargyloxycarbonyl groups and the like, and C1-C3 alkoxy C1-C3 groups.
Examples of the alkoxycarbonyl group include a methoxymethoxycarbonyl group, a 2-methoxyethoxycarbonyl group,
Ethoxyethoxycarbonyl group and the like,

Examples of the C1-C3 alkyl group represented by R ^13, a methyl group, an ethyl group, and examples of the C1-C6 alkyl group represented by R ^14, a methyl group, an ethyl group, iso- propyl group Examples of the C1-C6 haloalkyl group include a chloromethyl group, a bromomethyl group, a fluoromethyl group, a dichloromethyl group, a dibromomethyl group, and a difluoromethyl group. Examples of the hydroxy C1-C3 alkyl group include hydroxymethyl Group,
Examples of the C1-C3 alkoxy C1-C3 alkyl group include a methoxymethyl group, an ethoxymethyl group, and an iso-propyloxymethyl group, and a C1-C6 alkylcarbonyloxy C1-C3. Examples of the alkyl group include a methylcarbonyloxymethyl group and an ethylcarbonyloxymethyl group, and a C1-C6 haloalkylcarbonyloxy C1-
Examples of the C3 alkyl group include a trifluoromethylcarbonyloxymethyl group and a difluoromethylcarbonyloxymethyl group. Examples of the C1-C6 alkoxycarbonyl group include a methoxycarbonyl group, an ethoxycarbonyl group, a propyloxycarbonyl group, and an iso-propyl group. Oxycarbonyl group, butyloxycarbonyl group, i
Examples thereof include a so-butyloxycarbonyl group, a sec-butyloxycarbonyl group, a t-butyloxycarbonyl group, a pentyloxycarbonyl group, and a hexyloxycarbonyl group. Examples of the C1-C6 haloalkoxycarbonyl group include 2,2,2 -Trifluoroethoxycarbonyl group, 2-fluoroethoxycarbonyl group, 2-chloroethoxycarbonyl group, 2-bromoethoxycarbonyl group and the like. Examples of the C3-C8 cycloalkoxycarbonyl group include a cyclopropyloxycarbonyl group and a cyclobutyl group. An oxycarbonyl group, a cyclopentyloxycarbonyl group, a cyclohexyloxycarbonyl group and the like can be mentioned. As the C3-C6 alkenyloxycarbonyl group, an allyloxycarbonyl group and the like can be mentioned.
As the -C6 alkynyloxycarbonyl group, a propargyloxycarbonyl group and the like can be mentioned, and as the C1-C3 alkoxy C1-C3 alkoxycarbonyl group,
Methoxymethoxycarbonyl group, 2-methoxyethoxycarbonyl group, 2-ethoxyethoxycarbonyl group and the like,

Examples of the C1-C6 alkyl group represented by R ^15, a methyl group, an ethyl group, a propyl group, iso- propyl, butyl, iso- butyl group, sec- butyl group, t- butyl group, a pentyl group And a hexyl group, and the like, and examples of the C1-C6 haloalkyl group include a trifluoromethyl group, a difluoromethyl group, a 2-fluoroethyl group, a 2-chloroethyl group, and a 2-bromoethyl group. Examples of the group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and the like.
Examples of the 1-C3 alkyl group include a cyclopropylmethyl group, a cyclobutylmethyl group, a cyclopentylmethyl group,
Examples of the cyclohexylmethyl group include C3-C6 alkenyl groups such as allyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, and 1,1-dimethyl-2-propenyl. And a C3-C6 alkynyl group such as a propargyl group and a 1-methyl-2- group.
Propynyl group, 2-butynyl group, 1,1-dimethyl-2
-Propynyl group and the like, and as the cyano C1-C3 alkyl group, a cyanomethyl group, a 1-cyanoethyl group,
Examples thereof include a 2-cyanoethyl group and a 1-methyl-2-cyanoethyl group. Examples of the C1-C3 alkoxy C1-C3 alkyl group include a methoxymethyl group, a 2-methoxyethyl group, an ethoxymethyl group, and a 2-ethoxyethyl group. And examples of the C1-C3 alkylthio C1-C3 alkyl group include a methylthiomethyl group, a 2-ethylthioethyl group, a 2-methylthioethyl group, and the like.
Examples of the alkylcarbonyl group include an acetyl group, an ethylcarbonyl group, a propylcarbonyl group, an iso-propylcarbonyl group, a pivaloyl group, and the like.
Examples of the haloalkylcarbonyl group include a trifluoroacetyl group, a difluoroacetyl group, a trichloroacetyl group, and a dichloroacetyl group. Examples of the C3-C8 cycloalkylcarbonyl group include a cyclopropylcarbonyl group, a cyclopentylcarbonyl group, and a cyclohexylcarbonyl group. And examples of the carboxy C1-C3 alkyl group include a carboxymethyl group, a 1-carboxyethyl group, a 1-methyl-1-carboxyethyl group,
-Carboxypropyl group, 2-carboxyethyl group, 1
-Methyl-2-carbonylethyl group and the like, and C1
-C6 alkoxycarbonyl C1-C3 alkyl group includes methoxycarbonylmethyl group, ethoxycarbonylmethyl group, propyloxycarbonylmethyl group, is
o-propyloxycarbonylmethyl group, butyloxycarbonylmethyl group, iso-butyloxycarbonylmethyl group, sec-butyloxycarbonylmethyl group,
t-butyloxycarbonylmethyl group, pentyloxycarbonylmethyl group, iso-pentyloxycarbonylmethyl group, hexyloxycarbonylmethyl group, is
o-hexyloxycarbonylmethyl group, 1-methoxycarbonylethyl group, 1-ethoxycarbonylethyl group, 1- (propyloxycarbonyl) ethyl group, 1-
(Iso-propyloxycarbonyl) ethyl group, 1-
(Butyloxycarbonyl) ethyl group, 1- (iso-
Butyloxycarbonyl) ethyl group, 1- (sec-butyloxycarbonyl) ethyl group, 1- (t-butyloxycarbonyl) ethyl group, 1- (pentyloxycarbonyl) ethyl group, 1- (iso-pentyloxycarbonyl) Ethyl group, 1- (hexyloxycarbonyl)
Ethyl group, 1- (iso-hexyloxycarbonyl)
Ethyl group, 1-methyl-1- (methoxycarbonyl) ethyl group, 1-methyl-1- (ethoxycarbonyl) ethyl group, 1-methyl-1- (propyloxycarbonyl)
Ethyl group, 1-methyl-1- (iso-propyloxycarbonyl) ethyl group, 1-methyl-1- (butyloxycarbonyl) ethyl group, 1-methyl-1- (iso-
Butyloxycarbonyl) ethyl group, 1-methyl-1-
(Sec-butyloxycarbonyl) ethyl group, 1-methyl-1- (t-butyloxycarbonyl) ethyl group,
1-methyl-1- (pentyloxycarbonyl) ethyl group, 1-methyl-1- (iso-pentyloxycarbonyl) ethyl group, 1-methyl-1- (hexyloxycarbonyl) ethyl group, 1-methyl-1- (Iso-hexyloxycarbonyl) ethyl group and the like, and C1-
As the C6 haloalkoxycarbonyl C1-C3 alkyl group, a 2-fluoroethoxycarbonylmethyl group, 2
-Chloroethoxycarbonylmethyl group, 2-bromoethoxycarbonylmethyl group, 2,2,2-trifluoroethoxycarbonylmethyl group, 2-chloroethoxycarbonylmethyl group, 2-bromoethoxycarbonylmethyl group, 1- (2-fluoro An ethoxycarbonyl) ethyl group, a 1- (2-chloroethoxycarbonyl) ethyl group,
1- (2-bromoethoxycarbonyl) ethyl group, 1-
(2,2,2-trifluoroethoxycarbonyl) ethyl group, 1- (2-chloroethoxycarbonyl) ethyl group, 1- (2-bromoethoxycarbonyl) ethyl group,
1-methyl-1- (2-fluoroethoxycarbonyl)
Ethyl group, 1-methyl-1- (2-chloroethoxycarbonyl) ethyl group, 1-methyl-1- (2-bromoethoxycarbonyl) ethyl group, 1-methyl-1- (2,
2,2-trifluoroethoxycarbonyl) ethyl group,
A 1-methyl-1- (2-chloroethoxycarbonyl) ethyl group, a 1-methyl-1- (2-bromoethoxycarbonyl) ethyl group, and the like. Examples of the C3-C8 cycloalkoxycarbonyl C1-C3 alkyl group include: Cyclopropyloxycarbonylmethyl group, cyclobutyloxycarbonylmethyl group, cyclopentyloxycarbonylmethyl group, cyclohexyloxycarbonylmethyl group, 1-cyclopropyloxycarbonylethyl group, 1
-Cyclobutyloxycarbonylethyl group, 1-cyclopentyloxycarbonylethyl group, 1-cyclohexyloxycarbonylethyl group, 1-methyl- (1-cyclopropyloxycarbonyl) ethyl group, 1-methyl-
(1-cyclobutyloxycarbonyl) ethyl group, 1-
A methyl- (1-cyclopentyloxycarbonyl) ethyl group, a 1-methyl- (1-cyclohexyloxycarbonyl) ethyl group, and the like;

C3-C6 alkenyloxycarbonyl C
Examples of the 1-C3 alkyl group include an allyloxycarbonylmethyl group, a (1-methyl-2-propenyloxy) carbonylmethyl group, a 2-methyl-2-propenyloxycarbonylmethyl group, and a 1,1-dimethyl-2-propenyloxy group. Carbonylmethyl group, 1- (allyloxycarbonyl) ethyl group, 1- (1-methyl-2-propenyloxycarbonyl) ethyl group, 1- (2-methyl-2-propenyloxycarbonyl) ethyl group, 1- (1 , 1-
Dimethyl-2-propenyloxycarbonyl) ethyl group, 1-methyl-1- (allyloxycarbonyl) ethyl group, 1-methyl-1- (1-methyl-2-propenyloxycarbonyl) ethyl group, 1-methyl-1 − (2-
A methyl-2-propenyloxycarbonyl) ethyl group,
A 1-methyl-1- (1,1-dimethyl-2-propenyloxycarbonyl) ethyl group and the like, and C3-C6
Examples of the alkynyloxycarbonyl C1-C3 alkyl group include a propargyloxycarbonylmethyl group, a 1-methyl-2-propynyloxycarbonylmethyl group,
Butynyloxycarbonylmethyl group, 1,1-dimethyl-2-propynyloxycarbonylmethyl group, 1- (propargyloxycarbonyl) ethyl group, 1- (1-methyl-2-propynyloxycarbonyl) ethyl group, 1
-(2-butynyloxycarbonyl) ethyl group, 1-
(1,1-dimethyl-2-propynyloxycarbonyl) ethyl group, 1-methyl-1- (propargyloxycarbonyl) ethyl group, 1-methyl-1- (1-methyl-2-propynyloxycarbonyl) ethyl group, A 1-methyl-1- (2-butynyloxycarbonyl) ethyl group, a 1-methyl-1- (1,1-dimethyl-2-propynyloxycarbonyl) ethyl group, and the like;
C3 alkoxy C1-C3 alkoxycarbonyl C1-
Examples of the C3 alkyl group include a methoxymethoxycarbonylmethyl group, a 2-methoxyethoxycarbonylmethyl group,
Ethoxymethoxycarbonylmethyl group, 2-ethoxyethoxycarbonylmethyl group, 1- (methoxymethoxycarbonyl) ethyl group, 1- (2-methoxyethoxycarbonyl) ethyl group, 1- (ethoxymethoxycarbonyl) ethyl group, 1- (2 -Ethoxyethoxycarbonyl) ethyl group, 1-methyl-1- (methoxymethoxycarbonyl) ethyl group, 1-methyl-1- (2-methoxyethoxycarbonyl) ethyl group, 1-methyl-1- (ethoxymethoxycarbonyl) ethyl Group, 1-methyl-1
-(2-ethoxyethoxycarbonyl) ethyl group and the like, and carboxy C1-C3 alkoxycarbonyl C
Examples of the 1-C3 alkyl group include a carboxymethoxycarbonylmethyl group, 1- (carboxy) ethoxycarbonylmethyl group, 1- (carboxymethoxycarbonyl) ethyl group, 1- {1- (carboxy) ethoxycarbonyl} ethyl group, {1 -Methyl-1- (carboxy) ethoxy} carbonylmethyl group, 1- {1-methyl-1-
(Carboxy) ethoxycarbonyldiethyl group and the like. Examples of the C1-C6 alkoxycarbonyl C1-C3 alkoxycarbonyl C1-C3 alkyl group include a methoxycarbonylmethoxycarbonylmethyl group, a 1- (methoxycarbonyl) ethoxycarbonylmethyl group, −
(Methoxycarbonylmethoxycarbonyl) ethyl group,
1- {1- (methoxycarbonyl) ethoxycarbonyl} ethyl group, 1-methyl-1- (methoxycarbonyl) ethoxycarbonylmethyl group, 1- {1-methyl-
1- (methoxycarbonyl) ethoxycarbonyl} ethyl group, ethoxycarbonylmethoxycarbonylmethyl group, 1- (ethoxycarbonyl) ethoxycarbonylmethyl group, 1- (ethoxycarbonylmethoxycarbonyl) ethyl group, 1- {1- (ethoxycarbonyl) Ethoxycarbonyl @ ethyl group, 1-methyl-1- (ethoxycarbonyl) ethoxycarbonylmethyl group, 1- {1
-Methyl-1- (ethoxycarbonyl) ethoxycarbonyldiethyl group and the like;

C1-C6 haloalkoxycarbonyl C1
As the -C3 alkoxycarbonyl C1-C3 alkyl group, a 2-fluoroethoxycarbonylmethoxycarbonylmethyl group, a 1- (2-fluoroethoxycarbonyl) ethoxycarbonylmethyl group, a 1- (2-fluoroethoxycarbonylmethoxycarbonyl) ethyl group, 1
-{1- (2-fluoroethoxycarbonyl) ethoxycarbonyl} ethyl group, 1-methyl-1- (2-fluoroethoxycarbonyl) ethoxycarbonylmethyl group,
1- {1-methyl-1- (2-fluoroethoxycarbonyl) ethoxycarbonyl} ethyl group, 2-chloroethoxycarbonylmethoxycarbonylmethyl group, 1- (2
-Chloroethoxycarbonyl) ethoxycarbonylmethyl group, 1- (2-chloroethoxycarbonylmethoxycarbonyl) ethyl group, 1- {1- (2-chloroethoxycarbonyl) ethoxycarbonyl} ethyl group, 1-methyl-1- (2 -Chloroethoxycarbonyl) ethoxycarbonylmethyl group, 1- {1-methyl-1- (2-chloroethoxycarbonyl) ethoxycarbonyl} ethyl group, and the like, and C3-C8 cycloalkoxycarbonyl C1-C3 alkoxycarbonyl C1-C3 Examples of the alkyl group include a cyclopentyloxycarbonylmethoxycarbonylmethyl group, a 1- (cyclopentyloxycarbonyl) ethoxycarbonylmethyl group, a 1- (cyclopentyloxycarbonylmethoxycarbonyl) ethyl group,
1- {1- (cyclopentyloxycarbonyl) ethoxycarbonyl} ethyl group, 1-methyl-1- (cyclopentyloxycarbonyl) ethoxycarbonylmethyl group, 1- {1-methyl-1- (cyclopentyloxycarbonyl) ethoxycarbonyl} ethyl And C3-C6 alkenyloxycarbonyl C1-C3.
As the alkoxycarbonyl C1-C3 alkyl group,
An allyloxycarbonylmethoxycarbonylmethyl group,
1- (allyloxycarbonyl) ethoxycarbonylmethyl group, 1- (allyloxycarbonylmethoxycarbonyl) ethyl group, 1- {1- (allyloxycarbonyl) ethoxycarbonyl} ethyl group, 1-methyl-1-
(Allyloxycarbonyl) ethoxycarbonylmethyl group, 1- {1-methyl-1- (allyloxycarbonyl) ethoxycarbonyl} ethyl group, and the like.

C3-C6 alkynyloxycarbonyl C
Examples of the 1-C3 alkoxycarbonyl C1-C3 alkyl group include a propargyloxycarbonylmethoxycarbonylmethyl group and a 1- (propargyloxycarbonyl)
Ethoxycarbonylmethyl group, 1- (propargyloxycarbonylmethoxycarbonyl) ethyl group, 1- {1
-(Propargyloxycarbonyl) ethoxycarbonyl} ethyl group, 1-methyl-1- (propargyloxycarbonyl) ethoxycarbonylmethyl group, 1- {1-
Methyl-1- (propargyloxycarbonyl) ethoxycarbonyldiethyl group and the like, and the optionally substituted aryloxycarbonyl C1-C3 alkyl group include a phenoxycarbonylmethyl group, a 1-phenoxycarbonylethyl group, A methyl-1- (phenoxycarbonyl) ethyl group and the like, and an optionally substituted aryl C1-C3 alkoxycarbonyl C1-
Examples of the C3 alkyl group include a benzyloxycarbonylmethyl group, a 1-benzyloxycarbonylethyl group,
A methyl-1- (benzyloxycarbonyl) ethyl group,
A phenethyloxycarbonylmethyl group, a 1-phenethyloxycarbonylethyl group, a 1-methyl-1- (phenethyloxycarbonyl) ethyl group, and the like;
Examples of the C6 alkoxycarbonyl group include a methoxycarbonyl group, an ethoxycarbonyl group, a propyloxycarbonyl group, and an iso-propyloxycarbonyl group.

[0020] As C1-C3 alkyl group represented by R ¹⁷ include a methyl group, an ethyl group, a propyl group, an iso- propyl group, and the C1-C3 haloalkyl group, a chloromethyl group, a trifluoromethyl group and the like Raised, R
The C1-C3 alkyl group represented by ^18, a methyl group, an ethyl group, and examples of the C1-C6 alkoxycarbonyl group, a methoxycarbonyl group, an ethoxycarbonyl group and the like, a halogen atom represented by R ¹⁹ Are a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and the C1-C6 alkyl group is a methyl group,
Ethyl group, propyl group, iso-propyl group, butyl group, iso-butyl group, sec-butyl group, t-butyl group, pentyl group, hexyl group and the like, and C1-C6
Examples of the haloalkyl group include a trifluoromethyl group, a difluoromethyl group, a 2-fluoroethyl group, a 2-chloroethyl group, and a 2-bromoethyl group.
Examples of the alkoxy group include a methoxy group, an ethoxy group, a propyloxy group, an iso-propyloxy group, a butyloxy group, an iso-butyloxy group, a sec-butyloxy group, a t-butyloxy group, a pentyloxy group, and a hexyloxy group. , C1-C6 haloalkoxy groups include 2-fluoroethoxy group, 2-chloroethoxy group, 2-bromoethoxy group and the like, and C3-C8 cycloalkoxy groups include cyclopropyloxy group,
Examples thereof include a cyclobutyloxy group, a cyclopentyloxy group, and a cyclohexyloxy group. Examples of the C3-C6 alkenyloxy group include an allyloxy group and 1-methyl-2.
-Propenyloxy group, 2-methyl-2-propenyloxy group, 1,1-dimethyl-2-propenyloxy group and the like,

The C3-C6 alkynyloxy group includes
Propargyloxy group, 1-methyl-2-propynyloxy group, 2-butynyloxy group, 1,1-dimethyl-2
-Propynyloxy group and the like;
As the C3 alkoxy group, a carboxymethoxy group, 1
-Carboxyethoxy group, 1-methyl-1- (carboxy) ethoxy group and the like. Examples of the C1-C6 alkoxycarbonyl C1-C3 alkoxy group include a methoxycarbonylmethoxy group, an ethoxycarbonylmethoxy group,
Propyloxycarbonylmethoxy group, iso-propyloxycarbonylmethoxy group, butyloxycarbonylmethoxy group, iso-butyloxycarbonylmethoxy group, sec-butyloxycarbonylmethoxy group, t
-Butyloxycarbonylmethoxy group, pentyloxycarbonylmethoxy group, iso-pentyloxycarbonylmethoxy group, hexyloxycarbonylmethoxy group, iso-hexyloxycarbonylmethoxy group, 1
-Methoxycarbonylethoxy group, 1-ethoxycarbonylethoxy group, 1- (propyloxycarbonyl) ethoxy group, 1- (iso-propyloxycarbonyl)
Ethoxy group, 1- (butyloxycarbonyl) ethoxy group, 1- (iso-butyloxycarbonyl) ethoxy group, 1- (sec-butyloxycarbonyl) ethoxy group, 1- (t-butyloxycarbonyl) ethyl group,
-(Pentyloxycarbonyl) ethoxy group, 1- (i
so-pentyloxycarbonyl) ethoxy group, 1-
(Hexyloxycarbonyl) ethoxy group, 1- (is
o-hexyloxycarbonyl) ethoxy group, 1-methyl-1- (methoxycarbonyl) ethoxy group, 1-methyl-1- (ethoxycarbonyl) ethoxy group, 1-methyl-1- (propyloxycarbonyl) ethoxy group,
-Methyl-1- (iso-propyloxycarbonyl)
An ethoxy group, a 1-methyl-1- (butyloxycarbonyl) ethoxy group, a 1-methyl-1- (iso-butyloxycarbonyl) ethoxy group, a 1-methyl-1- (se
c-butyloxycarbonyl) ethoxy group, 1-methyl-1- (t-butyloxycarbonyl) ethoxy group, 1
-Methyl-1- (pentyloxycarbonyl) ethoxy group, 1-methyl-1- (iso-pentyloxycarbonyl) ethoxy group, 1-methyl-1- (hexyloxycarbonyl) ethoxy group, 1-methyl-1- ( iso-
Hexyloxycarbonyl) ethoxy group and the like;

C3-C8 cycloalkoxycarbonyl C
Examples of the 1-C3 alkoxy group include a cyclopropyloxycarbonylmethoxy group, a cyclobutyloxycarbonylmethoxy group, a cyclopentyloxycarbonylmethoxy group, a cyclohexyloxycarbonylmethoxy group,
Cyclopropyloxycarbonylethoxy, 1-cyclobutyloxycarbonylethoxy, 1-cyclopentyloxycarbonylethoxy, 1-cyclohexyloxycarbonylethoxy, 1-methyl-1- (cyclopropyloxycarbonyl) ethoxy, 1-methyl -1- (cyclobutyloxycarbonyl) ethoxy group,
1-methyl-1- (cyclopentyloxycarbonyl)
Examples thereof include an ethoxy group and a 1-methyl-1- (cyclohexyloxycarbonyl) ethoxy group. Examples of the C3-C6 alkenyloxycarbonyl C1-C3 alkoxy group include an allyloxycarbonylmethoxy group and a 1-methyl-
2-propenyloxycarbonylmethoxy group, 2-methyl-2-propenyloxycarbonylmethoxy group, 1,
1-dimethyl-2-propenyloxycarbonylmethoxy group, 1- (allyloxycarbonyl) ethoxy group, 1
-(1-methyl-2-propenyloxycarbonyl) ethoxy group, 1- (2-methyl-2-propenyloxycarbonyl) ethoxy group, 1- (1,1-dimethyl-2-)
Propenyloxycarbonyl) ethoxy group, 1-methyl-1- (allyloxycarbonyl) ethoxy group, 1-methyl-1- (1-methyl-2-propenyloxycarbonyl) ethoxy group, 1-methyl-1- (2- Methyl-2
-Propenyloxycarbonyl) ethoxy group, 1-methyl-1- (1,1-dimethyl-2-propenyloxycarbonyl) ethoxy group, and the like. Examples of the C3-C6 alkynyloxycarbonyl C1-C3 alkoxy group include propargyloxy. Carbonylmethoxy group, 1-methyl-2-propynyloxycarbonylmethoxy group, 2
-Butynyloxycarbonylmethoxy group, 1,1-dimethyl-2-propynyloxycarbonylmethoxy group, 1
-(Propargyloxycarbonyl) ethoxy group, 1-
(1-methyl-2-propynyloxycarbonyl) ethoxy group, 1- (2-butynyloxycarbonyl) ethoxy group, 1- (1,1-dimethyl-2-propynyloxycarbonyl) ethoxy group, 1-methyl-1 -(Propargyloxycarbonyl) ethoxy group, 1-methyl-1-
(1-methyl-2-propynyloxycarbonyl) ethoxy group, 1-methyl-1- (2-butynyloxycarbonyl) ethoxy group, 1-methyl-1- (1,1-dimethyl-2-propynyloxycarbonyl) Ethoxy groups and the like;

The halogen atom represented by R ²⁰ is a fluorine atom, a chlorine atom, a bromine atom, an iodine atom,
Examples of the 1-C6 alkyl group include a methyl group, an ethyl group, a propyl group, an iso-propyl group, a butyl group, an iso-butyl group, a sec-butyl group, a t-butyl group, a pentyl group, and a hexyl group. Examples of the C1-C6 haloalkyl group include a trifluoromethyl group, a difluoromethyl group, a 2-fluoroethyl group, a 2-chloroethyl group,
Bromoethyl group and the like; and C1-C6 alkoxy group includes methoxy group, ethoxy group, propyloxy group, iso-propyloxy group, butyloxy group, is
o-butyloxy group, sec-butyloxy group, t-butyloxy group, pentyloxy group, hexyloxy group and the like.
-Fluoroethoxy group, 2-chloroethoxy group, 2-bromoethoxy group and the like. Examples of the C3-C8 cycloalkoxy group include a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group and a cyclohexyloxy group. And the C3-C6 alkenyloxy group includes an allyloxy group, a 1-methyl-2-propenyloxy group, a 2-methyl-2-propenyloxy group,
1,1-dimethyl-2-propenyloxy group and the like. Examples of the C3-C6 alkynyloxy group include a propargyloxy group, a 1-methyl-2-propynyloxy group,
Examples thereof include a 2-butynyloxy group and a 1,1-dimethyl-2-propynyloxy group. Examples of the carboxy C1-C3 alkoxy group include a carboxymethoxy group, a 1-carboxyethoxy group, and a 1-methyl-1- (carboxy) ethoxy group. And C1-C6 alkoxycarbonyl C1-C3 alkoxy groups include methoxycarbonylmethoxy, ethoxycarbonylmethoxy, propyloxycarbonylmethoxy, iso-propyloxycarbonylmethoxy, butyloxycarbonylmethoxy, iso -Butyloxycarbonylmethoxy group, s
ec-butyloxycarbonylmethoxy group, t-butyloxycarbonylmethoxy group, pentyloxycarbonylmethoxy group, iso-pentyloxycarbonylmethoxy group, hexyloxycarbonylmethoxy group, iso
-Hexyloxycarbonylmethoxy group, 1-methoxycarbonylethoxy group, 1-ethoxycarbonylethoxy group, 1- (propyloxycarbonyl) ethoxy group,
1- (iso-propyloxycarbonyl) ethoxy group, 1- (butyloxycarbonyl) ethoxy group, 1-
(Iso-butyloxycarbonyl) ethoxy group, 1-
(Sec-butyloxycarbonyl) ethoxy group, 1-
(T-butyloxycarbonyl) ethyl group, 1- (pentyloxycarbonyl) ethoxy group, 1- (iso-pentyloxycarbonyl) ethoxy group, 1- (hexyloxycarbonyl) ethoxy group, 1- (iso-hexyloxycarbonyl) ) Ethoxy group, 1-methyl-1-
(Methoxycarbonyl) ethoxy group, 1-methyl-1-
(Ethoxycarbonyl) ethoxy group, 1-methyl-1-
(Propyloxycarbonyl) ethoxy group, 1-methyl-1- (iso-propyloxycarbonyl) ethoxy group, 1-methyl-1- (butyloxycarbonyl) ethoxy group, 1-methyl-1- (iso-butyloxycarbonyl) ) Ethoxy group, 1-methyl-1- (sec-butyloxycarbonyl) ethoxy group, 1-methyl-1-
(T-butyloxycarbonyl) ethoxy group, 1-methyl-1- (pentyloxycarbonyl) ethoxy group, 1
-Methyl-1- (iso-pentyloxycarbonyl)
An ethoxy group, a 1-methyl-1- (hexyloxycarbonyl) ethoxy group, a 1-methyl-1- (iso-hexyloxycarbonyl) ethoxy group, and the like;

C3-C8 cycloalkoxycarbonyl C
Examples of the 1-C3 alkoxy group include a cyclopropyloxycarbonylmethoxy group, a cyclobutyloxycarbonylmethoxy group, a cyclopentyloxycarbonylmethoxy group, a cyclohexyloxycarbonylmethoxy group,
Cyclopropyloxycarbonylethoxy, 1-cyclobutyloxycarbonylethoxy, 1-cyclopentyloxycarbonylethoxy, 1-cyclohexyloxycarbonylethoxy, 1-methyl- (1-cyclopropyloxycarbonyl) ethoxy, 1-methyl A-(1-cyclobutyloxycarbonyl) ethoxy group,
1-methyl- (1-cyclopentyloxycarbonyl)
Examples thereof include an ethoxy group and a 1-methyl- (1-cyclohexyloxycarbonyl) ethoxy group, and examples of the C3-C6 alkenyloxycarbonyl C1-C3 alkoxy group include an allyloxycarbonylmethoxy group and a 1-methyl-
2-propenyloxycarbonylmethoxy group, 2-methyl-2-propenyloxycarbonylmethoxy group, 1,
1-dimethyl-2-propenyloxycarbonylmethoxy group, 1- (allyloxycarbonyl) ethoxy group, 1
-(1-methyl-2-propenyloxycarbonyl) ethoxy group, 1- (2-methyl-2-propenyloxycarbonyl) ethoxy group, 1- (1,1-dimethyl-2-)
Propenyloxycarbonyl) ethoxy group, 1-methyl-1- (allyloxycarbonyl) ethoxy group, 1-methyl-1- (1-methyl-2-propenyloxycarbonyl) ethoxy group, 1-methyl-1- (2- Methyl-2
-Propenyloxycarbonyl) ethoxy group, 1-methyl-1- (1,1-dimethyl-2-propenyloxycarbonyl) ethoxy group, and the like. Examples of the C3-C6 alkynyloxycarbonyl C1-C3 alkoxy group include propargyloxy. Carbonylmethoxy group, 1-methyl-2-propynyloxycarbonylmethoxy group, 2
-Butynyloxycarbonylmethoxy group, 1,1-dimethyl-2-propynyloxycarbonylmethoxy group, 1
-(Propargyloxycarbonyl) ethoxy group, 1-
(1-methyl-2-propynyloxycarbonyl) ethoxy group, 1- (2-butynyloxycarbonyl) ethoxy group, 1- (1,1-dimethyl-2-propynyloxycarbonyl) ethoxy group, 1-methyl-1 -(Propargyloxycarbonyl) ethoxy group, 1-methyl-1-
(1-methyl-2-propynyloxycarbonyl) ethoxy group, 1-methyl-1- (2-butynyloxycarbonyl) ethoxy group, 1-methyl-1- (1,1-dimethyl-2-propynyloxycarbonyl) Ethoxy groups and the like;

Examples of the C1-C3 alkyl group represented by R ²¹ and R ²² include a methyl group, an ethyl group, and a propyl group. Examples of the C2-C5 alkylene group include an ethylene group, a trimethylene group, a tetramethylene group, Pentamethylene group and the like, and C1-C3 alkyleneoxy C1-
C3 or ethylene oxyethylene group is exemplified as the alkylene group, the C1-C3 alkyl group represented by R ²³ and R ^24, a methyl group, an ethyl group, a propyl group, and examples of the C2-C5 alkylene group , An ethylene group, a trimethylene group, a tetramethylene group, a pentamethylene group and the like.
Examples of the C3 alkylene group include an ethyleneoxyethylene group and the like; ^examples of the C1-C3 alkyl group represented by R ²⁵ include a methyl group and an ethyl group; examples of the C1-C6 alkoxycarbonyl group include a methoxycarbonyl group; Examples of the halogen atom represented by R ²⁶ are a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and the C1-C6 alkyl group includes a methyl group, an ethyl group, a propyl group, and the like. iso-propyl group, butyl group, iso-butyl group, sec-butyl group, t-butyl group, pentyl group, hexyl group and the like. As the C1-C6 haloalkyl group, a trifluoromethyl group, a difluoromethyl group, 2-fluoroethyl group, 2-chloroethyl group, 2-bromoethyl group and the like, and C1-C6 alcohol The sheet group, a methoxy group,
Ethoxy, propyloxy, iso-propyloxy, butyloxy, iso-butyloxy, se
Examples thereof include a c-butyloxy group, a t-butyloxy group, a pentyloxy group, and a hexyloxy group. Examples of the C1-C6 haloalkoxy group include a 2-fluoroethoxy group,
-Chloroethoxy group, 2-bromoethoxy group and the like. Examples of the C3-C8 cycloalkoxy group include a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group and a cyclohexyloxy group.
Examples of the 3-C6 alkenyloxy group include an allyloxy group, a 1-methyl-2-propenyloxy group, a 2-methyl-2-propenyloxy group, and a 1,1-dimethyl-2-propenyloxy group. Examples of the C3-C6 alkynyloxy group include a propargyloxy group, a 1-methyl-2-propynyloxy group, a 2-butynyloxy group,
Examples of the 1,1-dimethyl-2-propynyloxy group include carboxy C1-C3 alkoxy groups, such as carboxymethoxy, 1-carboxyethoxy, and 1-methyl-1- (carboxy) ethoxy. , C
Examples of the 1-C6 alkoxycarbonyl C1-C3 alkoxy group include a methoxycarbonylmethoxy group, an ethoxycarbonylmethoxy group, a propyloxycarbonylmethoxy group, an iso-propyloxycarbonylmethoxy group,
Butyloxycarbonylmethoxy group, iso-butyloxycarbonylmethoxy group, sec-butyloxycarbonylmethoxy group, t-butyloxycarbonylmethoxy group, pentyloxycarbonylmethoxy group, iso-
Pentyloxycarbonylmethoxy group, hexyloxycarbonylmethoxy group, iso-hexyloxycarbonylmethoxy group, 1-methoxycarbonylethoxy group,
1-ethoxycarbonylethoxy group, 1- (propyloxycarbonyl) ethoxy group, 1- (iso-propyloxycarbonyl) ethoxy group, 1- (butyloxycarbonyl) ethoxy group, 1- (iso-butyloxycarbonyl) ethoxy group , 1- (sec-butyloxycarbonyl) ethoxy group, 1- (t-butyloxycarbonyl) ethoxy group, 1- (pentyloxycarbonyl)
Ethoxy group, 1- (iso-pentyloxycarbonyl) ethoxy group, 1- (hexyloxycarbonyl) ethoxy group, 1- (iso-hexyloxycarbonyl)
Ethoxy group, 1-methyl-1- (methoxycarbonyl)
Ethoxy group, 1-methyl-1- (ethoxycarbonyl)
Ethoxy group, 1-methyl-1- (propyloxycarbonyl) ethoxy group, 1-methyl-1- (iso-propyloxycarbonyl) ethoxy group, 1-methyl-1-
(Butyloxycarbonyl) ethoxy group, 1-methyl-
A 1- (iso-butyloxycarbonyl) ethoxy group,
1-methyl-1- (sec-butyloxycarbonyl)
Ethoxy group, 1-methyl-1- (t-butyloxycarbonyl) ethoxy group, 1-methyl-1- (pentyloxycarbonyl) ethoxy group, 1-methyl-1- (iso
-Pentyloxycarbonyl) ethoxy group, 1-methyl-1- (hexyloxycarbonyl) ethoxy group, 1-
A methyl-1- (iso-hexyloxycarbonyl) ethoxy group and the like;

C3-C8 cycloalkoxycarbonyl C
Examples of the 1-C3 alkoxy group include a cyclopropyloxycarbonylmethoxy group, a cyclobutyloxycarbonylmethoxy group, a cyclopentyloxycarbonylmethoxy group, a cyclohexyloxycarbonylmethoxy group,
Cyclopropyloxycarbonylethoxy, 1-cyclobutyloxycarbonylethoxy, 1-cyclopentyloxycarbonylethoxy, 1-cyclohexyloxycarbonylethoxy, 1-methyl-1- (cyclopropyloxycarbonyl) ethoxy, 1-methyl -1- (cyclobutyloxycarbonyl) ethoxy group,
1-methyl-1- (cyclopentyloxycarbonyl)
Examples thereof include an ethoxy group and a 1-methyl-1- (cyclohexyloxycarbonyl) ethoxy group. Examples of the C3-C6 alkenyloxycarbonyl C1-C3 alkoxy group include an allyloxycarbonylmethoxy group and a 1-methyl-
2-propenyloxycarbonylmethoxy group, 2-methyl-2-propenyloxycarbonylmethoxy group, 1,
1-dimethyl-2-propenyloxycarbonylmethoxy group, 1- (allyloxycarbonyl) ethoxy group, 1
-(1-methyl-2-propenyloxycarbonyl) ethoxy group, 1- (2-methyl-2-propenyloxycarbonyl) ethoxy group, 1- (1,1-dimethyl-2-)
Propenyloxycarbonyl) ethoxy group, 1-methyl-1- (allyloxycarbonyl) ethoxy group, 1-methyl-1- (1-methyl-2-propenyloxycarbonyl) ethoxy group, 1-methyl-1- (2- Methyl-2
-Propenyloxycarbonyl) ethoxy group, 1-methyl-1- (1,1-dimethyl-2-propenyloxycarbonyl) ethoxy group, and the like. Examples of the C3-C6 alkynyloxycarbonyl C1-C3 alkoxy group include propargyloxy. Carbonylmethoxy group, 1-methyl-2-propynyloxycarbonylmethoxy group, 2
-Butynyloxycarbonylmethoxy group, 1,1-dimethyl-2-propynyloxycarbonylmethoxy group, 1
-(Propargyloxycarbonyl) ethoxy group, 1-
(1-methyl-2-propynyloxycarbonyl) ethoxy group, 1- (2-butynyloxycarbonyl) ethoxy group, 1- (1,1-dimethyl-2-propynyloxycarbonyl) ethoxy group, 1-methyl-1 -(Propargyloxycarbonyl) ethoxy group, 1-methyl-1-
(1-methyl-2-propynyloxycarbonyl) ethoxy group, 1-methyl-1- (2-butynyloxycarbonyl) ethoxy group, 1-methyl-1- (1,1-dimethyl-2-propynyloxycarbonyl) Ethoxy groups and the like;

The halogen atom represented by R ²⁷ includes a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
Examples of the 1-C6 alkyl group include a methyl group, an ethyl group, a propyl group, an iso-propyl group, a butyl group, an iso-butyl group, a sec-butyl group, a t-butyl group, a pentyl group, and a hexyl group. Examples of the C1-C6 haloalkyl group include a trifluoromethyl group, a difluoromethyl group, a 2-fluoroethyl group, a 2-chloroethyl group,
Bromoethyl group and the like; and C1-C6 alkoxy group includes methoxy group, ethoxy group, propyloxy group, iso-propyloxy group, butyloxy group, is
o-butyloxy group, sec-butyloxy group, t-butyloxy group, pentyloxy group, hexyloxy group and the like.
-Fluoroethoxy group, 2-chloroethoxy group, 2-bromoethoxy group and the like. Examples of the C3-C8 cycloalkoxy group include a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group and a cyclohexyloxy group. And the C3-C6 alkenyloxy group includes an allyloxy group, a 1-methyl-2-propenyloxy group, a 2-methyl-2-propenyloxy group,
1,1-dimethyl-2-propenyloxy group and the like. Examples of the C3-C6 alkynyloxy group include a propargyloxy group, a 1-methyl-2-propynyloxy group,
Examples thereof include a 2-butynyloxy group and a 1,1-dimethyl-2-propynyloxy group. Examples of the carboxy C1-C3 alkoxy group include a carboxymethoxy group, a 1-carboxyethoxy group, and a 1-methyl-1- (carboxy) ethoxy group. And C1-C6 alkoxycarbonyl C1-C3 alkoxy groups include methoxycarbonylmethoxy, ethoxycarbonylmethoxy, propyloxycarbonylmethoxy, iso-propyloxycarbonylmethoxy, butyloxycarbonylmethoxy, iso -Butyloxycarbonylmethoxy group, s
ec-butyloxycarbonylmethoxy group, t-butyloxycarbonylmethoxy group, pentyloxycarbonylmethoxy group, iso-pentyloxycarbonylmethoxy group, hexyloxycarbonylmethoxy group, iso
-Hexyloxycarbonylmethoxy group, 1-methoxycarbonylethoxy group, 1-ethoxycarbonylethoxy group, 1- (propyloxycarbonyl) ethoxy group,
1- (iso-propyloxycarbonyl) ethoxy group, 1- (butyloxycarbonyl) ethoxy group, 1-
(Iso-butyloxycarbonyl) ethoxy group, 1-
(Sec-butyloxycarbonyl) ethoxy group, 1-
(T-butyloxycarbonyl) ethoxy group, 1- (pentyloxycarbonyl) ethoxy group, 1- (iso-
(Pentyloxycarbonyl) ethoxy group, 1- (hexyloxycarbonyl) ethoxy group, 1- (iso-hexyloxycarbonyl) ethoxy group, 1-methyl-1-
(Methoxycarbonyl) ethoxy group, 1-methyl-1-
(Ethoxycarbonyl) ethoxy group, 1-methyl-1-
(Propyloxycarbonyl) ethoxy group, 1-methyl-1- (iso-propyloxycarbonyl) ethoxy group, 1-methyl-1- (butyloxycarbonyl) ethoxy group, 1-methyl-1- (iso-butyloxycarbonyl) ) Ethoxy group, 1-methyl-1- (sec-butyloxycarbonyl) ethoxy group, 1-methyl-1-
(T-butyloxycarbonyl) ethoxy group, 1-methyl-1- (pentyloxycarbonyl) ethoxy group, 1
-Methyl-1- (iso-pentyloxycarbonyl)
An ethoxy group, a 1-methyl-1- (hexyloxycarbonyl) ethoxy group, a 1-methyl-1- (iso-hexyloxycarbonyl) ethoxy group, and the like;

C3-C8 cycloalkoxycarbonyl C
Examples of the 1-C3 alkoxy group include a cyclopropyloxycarbonylmethoxy group, a cyclobutyloxycarbonylmethoxy group, a cyclopentyloxycarbonylmethoxy group, a cyclohexyloxycarbonylmethoxy group,
Cyclopropyloxycarbonylethoxy, 1-cyclobutyloxycarbonylethoxy, 1-cyclopentyloxycarbonylethoxy, 1-cyclohexyloxycarbonylethoxy, 1-methyl-1- (cyclopropyloxycarbonyl) ethoxy, 1-methyl -1- (cyclobutyloxycarbonyl) ethoxy group,
1-methyl-1- (cyclopentyloxycarbonyl)
Examples thereof include an ethoxy group and a 1-methyl-1- (cyclohexyloxycarbonyl) ethoxy group. Examples of the C3-C6 alkenyloxycarbonyl C1-C3 alkoxy group include an allyloxycarbonylmethoxy group and a 1-methyl-
2-propenyloxycarbonylmethoxy group, 2-methyl-2-propenyloxycarbonylmethoxy group, 1,
1-dimethyl-2-propenyloxycarbonylmethoxy group, 1- (allyloxycarbonyl) ethoxy group, 1
-(1-methyl-2-propenyloxycarbonyl) ethoxy group, 1- (2-methyl-2-propenyloxycarbonyl) ethoxy group, 1- (1,1-dimethyl-2-)
Propenyloxycarbonyl) ethoxy group, 1-methyl-1- (allyloxycarbonyl) ethoxy group, 1-methyl-1- (1-methyl-2-propenyloxycarbonyl) ethoxy group, 1-methyl-1- (2- Methyl-2
-Propenyloxycarbonyl) ethoxy group, 1-methyl-1- (1,1-dimethyl-2-propenyloxycarbonyl) ethoxy group, and the like. Examples of the C3-C6 alkynyloxycarbonyl C1-C3 alkoxy group include propargyloxy. Carbonylmethoxy group, 1-methyl-2-propynyloxycarbonylmethoxy group, 2
-Butynyloxycarbonylmethoxy group, 1,1-dimethyl-2-propynyloxycarbonylmethoxy group, 1
-(Propargyloxycarbonyl) ethoxy group, 1-
(1-methyl-2-propynyloxycarbonyl) ethoxy group, 1- (2-butynyloxycarbonyl) ethoxy group, 1- (1,1-dimethyl-2-propynyloxycarbonyl) ethoxy group, 1-methyl-1 -(Propargyloxycarbonyl) ethoxy group, 1-methyl-1-
(1-methyl-2-propynyloxycarbonyl) ethoxy group, 1-methyl-1- (2-butynyloxycarbonyl) ethoxy group, 1-methyl-1- (1,1-dimethyl-2-propynyloxycarbonyl) Ethoxy groups and the like;

C represented by R ²⁸ , R ²⁹ , R ³⁰ and R ³¹
Examples of the 1-C3 alkyl group include a methyl group and an ethyl group. Examples of the halogen atom represented by R ³² , R ³³ and R ³⁴ include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom. -C3 alkyl groups include methyl group, ethyl group, propyl group and iso-propyl group, and C1-C3 haloalkyl groups include trifluoromethyl group, difluoromethyl group, fluoromethyl group, chloromethyl group and bromomethyl group. And C1-C
Examples of the 6 alkoxycarbonyl group include a methoxycarbonyl group, an ethoxycarbonyl group, a propyloxycarbonyl group, and an iso-propyloxycarbonyl group. Examples of the C3-C8 cycloalkoxycarbonyl group include a cyclopropyloxycarbonyl group and a cyclobutyloxy group. Carbonyl group, cyclopentyloxycarbonyl group, cyclohexyloxycarbonyl group and the like,
Examples of the C3-C6 alkenyloxycarbonyl group include an allyloxycarbonyl group, a 1-methyl-2-propenyloxycarbonyl group, a 2-methyl-2-propenyloxycarbonyl group, and the like. As the C3-C6 alkynyloxycarbonyl group, , A propargyloxycarbonyl group, a 1-methyl-2-propynyloxycarbonyl group, a 2-butynyloxycarbonyl group, and the like. Examples of the carboxyl C1-C3 alkyl group include a carboxymethyl group, a 1-carboxyethyl group, Methyl-1-
(Carboxy) ethyl group and the like, and C1-C6 alkoxycarbonyl C1-C3 alkyl group includes methoxycarbonylmethyl group, ethoxycarbonylmethyl group, propyloxycarbonylmethyl group, iso-propyloxycarbonylmethyl group, butyloxycarbonyl Methyl group, iso-butyloxycarbonylmethyl group, sec-butyloxycarbonylmethyl group, t-butyloxycarbonylmethyl group, pentyloxycarbonylmethyl group, iso-pentyloxycarbonylmethyl group, hexyloxycarbonylmethyl group, iso-hexyl Oxycarbonylmethyl group, 1-methoxycarbonylethyl group, 1-ethoxycarbonylethyl group, 1-
(Propyloxycarbonyl) ethyl group, 1- (iso
-Propyloxycarbonyl) ethyl group, 1- (butyloxycarbonyl) ethyl group, 1- (iso-butyloxycarbonyl) ethyl group, 1- (sec-butyloxycarbonyl) ethyl group, 1- (t-butyloxycarbonyl) ) Ethyl group, 1- (pentyloxycarbonyl)
Ethyl group, 1- (iso-pentyloxycarbonyl)
Ethyl group, 1- (hexyloxycarbonyl) ethyl group, 1- (iso-hexyloxycarbonyl) ethyl group, 1-methyl-1- (methoxycarbonyl) ethyl group, 1-methyl-1- (ethoxycarbonyl) ethyl group 1-methyl-1- (propyloxycarbonyl) ethyl group, 1-methyl-1- (iso-propyloxycarbonyl) ethyl group, 1-methyl-1- (butyloxycarbonyl) ethyl group, 1-methyl-1 -(Iso-butyloxycarbonyl) ethyl group, 1-methyl-1-
(Sec-butyloxycarbonyl) ethyl group, 1-methyl-1- (t-butyloxycarbonyl) ethyl group,
1-methyl-1- (pentyloxycarbonyl) ethyl group, 1-methyl-1- (iso-pentyloxycarbonyl) ethyl group, 1-methyl-1- (hexyloxycarbonyl) ethyl group, 1-methyl-1- (Iso-hexyloxycarbonyl) ethyl group and the like,

C3-C8 cycloalkoxycarbonyl C
Examples of the 1-C3 alkyl group include cyclopropyloxycarbonylmethyl, cyclobutyloxycarbonylmethyl, cyclopentyloxycarbonylmethyl, cyclohexyloxycarbonylmethyl, 1-cyclopropyloxycarbonylethyl, and 1-cyclobutyloxycarbonylethyl. Group, 1-cyclopentyloxycarbonylethyl group, 1-cyclohexyloxycarbonylethyl group, 1-methyl-1- (cyclopropyloxycarbonyl) ethyl group, 1-methyl-1- (cyclobutyloxycarbonyl) ethyl group, 1- Methyl-1- (cyclopentyloxycarbonyl) ethyl group, 1-methyl-
A 1- (cyclohexyloxycarbonyl) ethyl group and the like, and C3-C6 alkenyloxycarbonyl C1
As the -C3 alkyl group, an allyloxycarbonylmethyl group, a 1-methyl-2-propenyloxycarbonylmethyl group, a 2-methyl-2-propenyloxycarbonylmethyl group, a 1,1-dimethyl-2-propenyloxycarbonylmethyl group , 1- (allyloxycarbonyl)
Ethyl group, 1- (1-methyl-2-propenyloxycarbonyl) ethyl group, 1- (2-methyl-2-propenyloxycarbonyl) ethyl group, 1- (1,1-dimethyl-2-propenyloxycarbonyl) Ethyl group, 1-
Methyl-1- (allyloxycarbonyl) ethyl group, 1
-Methyl-1- (1-methyl-2-propenyloxycarbonyl) ethyl group, 1-methyl-1- (2-methyl-
2-propenyloxycarbonyl) ethyl group, 1-methyl-1- (1,1-dimethyl-2-propenyloxycarbonyl) ethyl group, and the like. Examples of the C3-C6 alkynyloxycarbonyl C1-C3 alkyl group include propargyl. Oxycarbonylmethyl group, 1-methyl-2
-Propynyloxycarbonyltyl group, 2-butynyloxycarbonylmethyl group, 1,1-dimethyl-2-propynyloxycarbonylmethyl group, 1- (propargyloxycarbonyl) ethyl group, 1- (1-methyl-2-
A propynyloxycarbonyl) ethyl group, a 1- (2-butynyloxycarbonyl) ethyl group, a 1- (1,1-dimethyl-2-propynyloxycarbonyl) ethyl group,
1-methyl-1- (propargyloxycarbonyl) ethyl group, 1-methyl-1- (1-methyl-2-propynyloxycarbonyl) ethyl group, 1-methyl-1- (2
-Butynyloxycarbonyl) ethyl group, 1-methyl-
A 1- (1,1-dimethyl-2-propynyloxycarbonyl) ethyl group; and carboxyl C1-C3.
Examples of the alkoxy group include a carboxymethoxy group, a 1-carboxyethoxy group, and 1-methyl-1- (carboxy)
Ethoxy groups and the like,

C1-C6 alkoxycarbonyl C1-C
Examples of the 3 alkoxy groups include methoxycarbonylmethoxy, ethoxycarbonylmethoxy, propyloxycarbonylmethoxy, iso-propyloxycarbonylmethoxy, butyloxycarbonylmethoxy, i
so-butyloxycarbonylmethoxy group, sec-butyloxycarbonylmethoxy group, t-butyloxycarbonylmethoxy group, pentyloxycarbonylmethoxy group, iso-pentyloxycarbonylmethoxy group,
Hexyloxycarbonylmethoxy group, iso-hexyloxycarbonylmethoxy group, 1-methoxycarbonylethoxy group, 1-ethoxycarbonylethoxy group, 1
-(Propyloxycarbonyl) ethoxy group, 1- (i
so-propyloxycarbonyl) ethoxy group, 1-
(Butyloxycarbonyl) ethoxy group, 1- (iso
-Butyloxycarbonyl) ethoxy group, 1- (sec
-Butyloxycarbonyl) ethoxy group, 1- (t-butyloxycarbonyl) ethoxy group, 1- (pentyloxycarbonyl) ethoxy group, 1- (iso-pentyloxycarbonyl) ethoxy group, 1- (hexyloxycarbonyl) ethoxy Group, 1- (iso-hexyloxycarbonyl) ethoxy group, 1-methyl-1- (methoxycarbonyl) ethoxy group, 1-methyl-1- (ethoxycarbonyl) ethoxy group, 1-methyl-1- (propyloxycarbonyl ) Ethoxy group, 1-methyl-1-
(Iso-propyloxycarbonyl) ethoxy group, 1
-Methyl-1- (butyloxycarbonyl) ethoxy group, 1-methyl-1- (iso-butyloxycarbonyl) ethoxy group, 1-methyl-1- (sec-butyloxycarbonyl) ethoxy group, 1-methyl-1 -(T-
Butyloxycarbonyl) ethoxy group, 1-methyl-1
-(Pentyloxycarbonyl) ethoxy group, 1-methyl-1- (iso-pentyloxycarbonyl) ethoxy group, 1-methyl-1- (hexyloxycarbonyl)
An ethoxy group, a 1-methyl-1- (iso-hexyloxycarbonyl) ethoxy group and the like can be mentioned, and the C3-C8 cycloalkoxycarbonyl C1-C3 alkoxy group includes a cyclopropyloxycarbonylmethoxy group and a cyclobutyloxycarbonylmethoxy group. , Cyclopentyloxycarbonylmethoxy group, cyclohexyloxycarbonylmethoxy group, 1-cyclopropyloxycarbonylethoxy group, 1-cyclobutyloxycarbonylethoxy group, 1-cyclopentyloxycarbonylethoxy group, 1-cyclohexyloxycarbonylethoxy group, 1-methyl -1- (cyclopropyloxycarbonyl) ethoxy group, 1-methyl-1- (cyclobutyloxycarbonyl) ethoxy group, 1-methyl-1- (cyclopentyloxyca Boniru) ethoxy group, 1-methyl -
A 1- (cyclohexyloxycarbonyl) ethoxy group and the like;

C3-C6 alkenyloxycarbonyl C
Examples of the 1-C3 alkoxy group include an allyloxycarbonylmethoxy group, a 1-methyl-2-propenyloxycarbonylmethoxy group, a 2-methyl-2-propenyloxycarbonylmethoxy group, and a 1,1-dimethyl-2-propenyloxycarbonylmethoxy group. Group, 1- (allyloxycarbonyl) ethoxy group, 1- (1-methyl-2-propenyloxycarbonyl) ethoxy group, 1- (2-methyl-2-propenyloxycarbonyl) ethoxy group, 1
-(1,1-dimethyl-2-propenyloxycarbonyl) ethoxy group, 1-methyl-1- (allyloxycarbonyl) ethoxy group, 1-methyl-1- (1-methyl-
2-propenyloxycarbonyl) ethoxy group, 1-methyl-1- (2-methyl-2-propenyloxycarbonyl) ethoxy group, 1-methyl-1- (1,1-dimethyl-2-propenyloxycarbonyl) ethoxy group And the like, and C3-C6 alkynyloxycarbonyl C1
Examples of the -C3 alkoxy group include a propargyloxycarbonylmethoxy group, a 1-methyl-2-propynyloxycarbonylmethoxy group, a 2-butynyloxycarbonylmethoxy group, a 1,1-dimethyl-2-propynyloxycarbonylmethoxy group, (Propargyloxycarbonyl) ethoxy group, 1- (1-methyl-2-propynyloxycarbonyl) ethoxy group, 1- (2-butynyloxycarbonyl) ethoxy group, 1- (1,1-dimethyl-2-propynyloxy) Carbonyl) ethoxy group, 1
-Methyl-1- (propargyloxycarbonyl) ethoxy group, 1-methyl-1- (1-methyl-2-propynyloxycarbonyl) ethoxy group, 1-methyl-1-
(2-butynyloxycarbonyl) ethoxy group, 1-methyl-1- (1,1-dimethyl-2-propynyloxycarbonyl) ethoxy group and the like.
Examples of the 1-C3 alkylthio group include a carboxymethylthio group, a 1-carboxyethylthio group, and a 1-methyl-1-
(Carboxy) ethylthio group and the like, and C1-C6
Examples of the alkoxycarbonyl C1-C3 alkylthio group include methoxycarbonylmethylthio, ethoxycarbonylmethylthio, propyloxycarbonylmethylthio, iso-propyloxycarbonylmethylthio, butyloxycarbonylmethylthio, iso-butyloxycarbonylmethylthio, sec- Butyloxycarbonylmethylthio group, t-butyloxycarbonylmethylthio group, pentyloxycarbonylmethylthio group, iso-pentyloxycarbonylmethylthio group, hexyloxycarbonylmethylthio group, iso-
Hexyloxycarbonylmethylthio group, 1-methoxycarbonylethylthio group, 1-ethoxycarbonylethylthio group, 1- (propyloxycarbonyl) ethylthio group, 1- (iso-propyloxycarbonyl) ethylthio group, 1- (butyloxycarbonyl ) Ethylthio, 1- (iso-butyloxycarbonyl) ethylthio, 1- (sec-butyloxycarbonyl) ethylthio, 1- (t-butyloxycarbonyl) ethylthio, 1- (pentyloxycarbonyl) ethylthio, 1- (iso-pentyloxycarbonyl) ethylthio group, 1- (hexyloxycarbonyl) ethylthio group, 1- (iso-hexyloxycarbonyl) ethylthio group, 1-methyl-1- (methoxycarbonyl) ethylthio group, 1-methyl 1- (ethoxycarbonyl) ethylthio group, 1-methyl-1- (propyl oxycarbonyl) ethylthio group, 1-methyl-1- (an iso-propyl oxycarbonyl) ethylthio group, 1-methyl-1
-(Butyloxycarbonyl) ethylthio group, 1-methyl-1- (iso-butyloxycarbonyl) ethylthio group, 1-methyl-1- (sec-butyloxycarbonyl) ethylthio group, 1-methyl-1- (t- Butyloxycarbonyl) ethylthio group, 1-methyl-1- (pentyloxycarbonyl) ethylthio group, 1-methyl-
A 1- (iso-pentyloxycarbonyl) ethylthio group, a 1-methyl-1- (hexyloxycarbonyl) ethylthio group, a 1-methyl-1- (iso-hexyloxycarbonyl) ethylthio group, and the like;

C3-C8 cycloalkoxycarbonyl C
Examples of the 1-C3 alkylthio group include a cyclopropyloxycarbonylmethylthio group, a cyclobutyloxycarbonylmethylthio group, a cyclopentyloxycarbonylmethylthio group, a cyclohexyloxycarbonylmethylthio group, a 1-cyclopropyloxycarbonylethylthio group, and a 1-cyclobutyloxycarbonyl Ethylthio group,
1-cyclopentyloxycarbonylethylthio group, 1
-Cyclohexyloxycarbonylethylthio group, 1-
Methyl-1- (cyclopropyloxycarbonyl) ethylthio group, 1-methyl-1- (cyclobutyloxycarbonyl) ethylthio group, 1-methyl-1- (cyclopentyloxycarbonyl) ethylthio group, 1-methyl-1
-(Cyclohexyloxycarbonyl) ethylthio group and the like, and C3-C6 alkenyloxycarbonyl C
Examples of the 1-C3 alkylthio group include an allyloxycarbonylmethylthio group, a 1-methyl-2-propenyloxycarbonylmethylthio group, a 2-methyl-2-propenyloxycarbonylmethylthio group, and a 1,1-dimethyl-2 group.
-Propenyloxycarbonylmethylthio group, 1- (allyloxycarbonyl) ethylthio group, 1- (1-methyl-2-propenyloxycarbonyl) ethylthio group,
1- (2-methyl-2-propenyloxycarbonyl)
Ethylthio group, 1- (1,1-dimethyl-2-propenyloxycarbonyl) ethylthio group, 1-methyl-1-
(Allyloxycarbonyl) ethylthio group, 1-methyl-1- (1-methyl-2-propenyloxycarbonyl) ethylthio group, 1-methyl-1- (2-methyl-2
-Propenyloxycarbonyl) ethylthio group, 1-methyl-1- (1,1-dimethyl-2-propenyloxycarbonyl) ethylthio group, and the like. Examples of the C3-C6 alkynyloxycarbonyl C1-C3 alkylthio group include propargyloxy. Carbonylmethylthio group,
1-methyl-2-propynyloxycarbonylmethylthio group, 2-butynyloxycarbonylmethylthio group,
1,1-dimethyl-2-propynyloxycarbonylmethylthio group, 1- (propargyloxycarbonyl) ethylthio group, 1- (1-methyl-2-propynyloxycarbonyl) ethylthio group, 1- (2-butynyloxycarbonyl) Ethylthio group, 1- (1,1-dimethyl-
2-propynyloxycarbonyl) ethylthio group, 1-
Methyl-1- (propargyloxycarbonyl) ethylthio group, 1-methyl-1- (1-methyl-2-propynyloxycarbonyl) ethylthio group, 1-methyl-1-
(2-butynyloxycarbonyl) ethylthio group, 1-
Methyl-1- (1,1-dimethyl-2-propynyloxycarbonyl) ethylthio group and the like, and as the carboxyl C1-C3 alkylamino group, a carboxymethylamino group, a 1-carboxyethylamino group, a 1-methyl- A 1- (carboxy) ethylamino group and the like;

C1-C6 alkoxycarbonyl C1-C
3 Examples of the alkylamino group include a methoxycarbonylmethylamino group, an ethoxycarbonylmethylamino group, a propyloxycarbonylmethylamino group, an iso-propyloxycarbonylmethylamino group, a butyloxycarbonylmethylamino group, and an iso-butyloxycarbonylmethylamino group. , Sec-butyloxycarbonylmethylamino group, t-butyloxycarbonylmethylamino group, pentyloxycarbonylmethylamino group, is
o-pentyloxycarbonylmethylamino group, hexyloxycarbonylmethylamino group, iso-hexyloxycarbonylmethylamino group, 1-methoxycarbonylethylamino group, 1-ethoxycarbonylethylamino group, 1- (propyloxycarbonyl) ethylamino Group, 1- (iso-propyloxycarbonyl) ethylthio group, 1- (butyloxycarbonyl) ethylamino group, 1- (iso-butyloxycarbonyl) ethylamino group, 1- (sec-butyloxycarbonyl) ethylamino group A 1- (t-butyloxycarbonyl) ethylamino group, a 1- (pentyloxycarbonyl) ethylamino group, a 1- (iso-pentyloxycarbonyl) ethylamino group, a 1- (hexyloxycarbonyl) ethylamino group, - (an iso-hexyloxy carbonyl) ethylamino group, 1-methyl-1- (methoxycarbonyl) ethylamino group, 1-methyl-1- (ethoxycarbonyl) ethyl group, 1-methyl-1-
(Propyloxycarbonyl) ethylamino group, 1-methyl-1- (iso-propyloxycarbonyl) ethylamino group, 1-methyl-1- (butyloxycarbonyl) ethylamino group, 1-methyl-1- (iso- Butyloxycarbonyl) ethylamino group, 1-methyl-1
-(Sec-butyloxycarbonyl) ethylamino group, 1-methyl-1- (t-butyloxycarbonyl)
Ethylamino group, 1-methyl-1- (pentyloxycarbonyl) ethylamino group, 1-methyl-1- (iso
-Pentyloxycarbonyl) ethylamino group, 1-methyl-1- (hexyloxycarbonyl) ethylamino group, 1-methyl-1- (iso-hexyloxycarbonyl) ethylamino group and the like, and C3-C8 cycloalkoxy is exemplified. Examples of the carbonyl C1-C3 alkylamino group include a cyclopropyloxycarbonylmethylamino group, a cyclobutyloxycarbonylmethylamino group, a cyclopentyloxycarbonylmethylamino group, a cyclohexyloxycarbonylmethylamino group, a 1-cyclopropyloxycarbonylethylamino group, 1-cyclobutyloxycarbonylethylamino group, 1-cyclopentyloxycarbonylethylamino group, 1-cyclohexyloxycarbonylethylamino group, 1-methyl-
1- (cyclopropyloxycarbonyl) ethylamino group, 1-methyl-1- (cyclobutyloxycarbonyl) ethylamino group, 1-methyl-1- (cyclopentyloxycarbonyl) ethylamino group, 1-methyl-1
-(Cyclohexyloxycarbonyl) ethylamino group and the like,

C3-C6 alkenyloxycarbonyl C
Examples of the 1-C3 alkylamino group include an allyloxycarbonylmethylamino group, a 1-methyl-2-propenyloxycarbonylmethylamino group, a 2-methyl-2-propenyloxycarbonylmethylamino group, and a 1,1-dimethyl-2- group. A propenyloxycarbonylmethylamino group, a 1- (allyloxycarbonyl) ethylamino group,
1- (1-methyl-2-propenyloxycarbonyl)
Ethylamino group, 1- (2-methyl-2-propenyloxycarbonyl) ethylamino group, 1- (1,1-dimethyl-2-propenyloxycarbonyl) ethylamino group, 1-methyl-1- (allyloxycarbonyl ) Ethylamino group, 1-methyl-1- (1-methyl-2-propenyloxycarbonyl) ethylamino group, 1-methyl-1- (2-methyl-2-propenyloxycarbonyl) ethylamino group, 1-methyl -1- (1,1-dimethyl-2-propenyloxycarbonyl) ethylamino group and the like. Examples of the C3-C6 alkynyloxycarbonyl C1-C3 alkylamino group include a propargyloxycarbonylmethylamino group and a 1-methyl- 2-propynyloxycarbonylmethylamino group, 2-butynyloxycarbonyl Chiruamino group, 1,1-dimethyl-2-propynyloxy carbonyl methylamino group, 1
-(Propargyloxycarbonyl) ethylamino group,
1- (1-methyl-2-propynyloxycarbonyl)
Ethylamino group, 1- (2-butynyloxycarbonyl) ethylamino group, 1- (1,1-dimethyl-2-propynyloxycarbonyl) ethylamino group, 1-methyl-1- (propargyloxycarbonyl) ethylamino Group, 1-methyl-1- (1-methyl-2-propynyloxycarbonyl) ethylamino group, 1-methyl-1-
(2-butynyloxycarbonyl) ethylamino group, 1
-Methyl-1- (1,1-dimethyl-2-propynyloxycarbonyl) ethylamino group and the like, and C1-
As the C6 alkoxy group, a methoxy group, an ethoxy group,
iso-propyloxy group and the like, and C3-C6 alkenyloxy group include allyl and the like.
The -C6 alkynyloxy group includes a propargyl group and the like, and the C1-C6 alkylcarbonyloxy group includes a methylcarbonyloxy group and the like.
Examples of the -C6 alkoxycarbonyloxy group include a methoxycarbonyloxy group and an ethoxycarbonyloxy group, and examples of the C1-C6 alkylthio group include a methylthio group, an ethylthio group and an iso-propylthio group, and a C3-C6 alkenyl group. Examples of the thio group include an allylthio group, and examples of the C3-C6 alkynylthio group include a propargylthio group.
Examples of the alkylcarbonylthio group include a methylcarbonylthio group and the like, examples of the C1-C6 alkoxycarbonylthio group include a methoxycarbonylthio group, and examples of the C1-C6 alkylamino group include a methylamino group and an ethylamino group. And the like. Examples of the C3-C6 alkenylamino group include an allylamino group.
Examples of the C3-C6 alkynylamino group include a propargylamino group, and examples of the C1-C6 alkylcarbonylamino group include an acetylamino group.
Examples of the -C6 alkoxycarbonylamino group include a methoxycarbonylamino group and an ethoxycarbonylamino group. The compound of the present invention has stereoisomers related to asymmetric carbon atoms, and each of the stereoisomers and a mixture thereof are also included in the compound of the present invention.

Among the compounds of the present invention, preferred substituents in terms of herbicidal efficacy include a trifluoromethyl group as R ^{1 and a} group represented by the general formula Q1 as Q. Preferred substituents for Q1 include a hydrogen atom or a fluorine atom for R ³ , an oxygen atom or a sulfur atom for Z, and a propargyl group or an allyl group for R ¹⁵ .

Next, the method for producing the compound of the present invention will be described in more detail. The compound of the present invention can be produced by the following production method. General formula [II] [Wherein, R ¹ and Q represent the same meaning as described above. Wherein the amide compound and a cyanate are reacted in the presence of a protonic acid. In the present invention, the cyanate includes both cyanate and isocyanate in a narrow sense. Examples of the cyanate in a narrow sense include alkali metal cyanates (eg, sodium cyanate, potassium cyanate, etc.), and examples of the isocyanate include silver isocyanate. The reaction temperature of the reaction is in the range of −20 ° C. to 50 ° C., preferably 10 ° C.
４５45 ° C. The amount of the reagent used for the reaction is usually 1 to 10 mol, preferably 1 to 1 mol per 1 mol of the amide compound represented by the general formula [II].
２2 mol. The amount of the protonic acid is usually 1 mol to a large excess, preferably 1 to 50 mol per mol of cyanate.
Is a mole. Examples of the type of protonic acid include aliphatic carboxylic acids such as acetic acid, propionic acid, and butyric acid, benzoic acid, and 4-carboxylic acid.
Examples thereof include aromatic carboxylic acids such as nitrobenzoic acid, sulfonic acids such as paratoluenesulfonic acid and methanesulfonic acid, and inorganic acids such as hydrochloric acid and sulfuric acid. In addition, the reaction can use a solvent that is inert under the above conditions. Examples of such solvents include pentane, hexane, heptane, cyclopentane, aliphatic hydrocarbons such as cyclohexane, dichloromethane, chloroform, aliphatic halogenated hydrocarbons such as 1,2-dichloroethane, benzene,
Aromatic hydrocarbons such as toluene and xylene, aromatic halogenated hydrocarbons such as chlorobenzene and m-dichlorobenzene, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclopentanone and cyclohexanone, diethyl ether, t- Butyl methyl ether, diethylene glycol dimethyl ether, 1,4-
Ethers such as dioxane and tetrahydrofuran; alcohols such as methanol, ethanol, isopropanol and n-propanol; amides such as N, N-dimethylformamide and N, N-dimethylacetamide; and sulfur-containing compounds such as dimethylsulfoxide and sulfolane. And nitro compounds such as nitromethane, nitroethane and 2-nitropropane; aliphatic nitriles such as acetonitrile; and mixtures thereof. After completion of the reaction, the reaction solution is poured into water and neutralized if necessary. Thereafter, the precipitated crystals are collected by filtration and dried, or extracted with an organic solvent, and the organic layer is dried and concentrated to obtain the target compound. The compound can be purified by an operation such as recrystallization or column chromatography.

In the production method, the compound represented by the general formula [I
Instead of reacting the amide compound represented by the formula (I) with a cyanate in the presence of a protonic acid, it is also possible to react the amide compound represented by the general formula [II] with a cyanic acid in an inert solvent. is there. Cyanic acid is described in J. Am. Org. C
hem. 28, pp586 (1963), or a method in which an alkali metal cyanate and a protonic acid are allowed to act.

The amide compound represented by the general formula [II] can be produced by the following production method. General formula [III] [Wherein, Q represents the same meaning as described above. An aniline compound represented by the general formula [IV] [Wherein, R ¹ has the same meaning as described above, and R ³² represents a methyl group or an ethyl group. ] In the solvent or in the absence of a solvent. The reaction temperature of the reaction is usually from room temperature to 150 ° C. or, when a solvent is used, from room temperature to the boiling point of the solvent used. Further, in order to increase the reaction rate, by-product alcohol (methanol or ethanol) may be distilled off from the reaction system, and a small amount of acid or base may be added. The amount of the acetic acid ester compound represented by the general formula [IV] to be subjected to the reaction is usually 1 to 5 mol based on the aniline compound represented by the general formula [III]. Examples of the acid added to increase the reaction rate include protonic acids such as p-toluenesulfonic acid and methanesulfonic acid, and the amount of the acid added is 0.05 to the aniline compound represented by the general formula [III]. The base is exemplified by tertiary amines such as triethylamine, tributylamine and N, N-dimethylaniline; pyridines such as pyridine; and inorganic bases such as potassium carbonate and sodium hydride. The addition amount is 0.05 to 1 mol based on the aniline compound represented by the general formula [III]. As the solvent, pentane, hexane, heptane, cyclopentane, aliphatic hydrocarbons such as cyclohexane, dichloromethane, chloroform, aliphatic halogenated hydrocarbons such as 1,2-dichloroethane, benzene,
Aromatic hydrocarbons such as toluene and xylene, aromatic halogenated hydrocarbons such as chlorobenzene and m-dichlorobenzene, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclopentanone and cyclohexanone, diethyl ether, t- Butyl methyl ether, diethylene glycol dimethyl ether, 1,4-
Ethers such as dioxane and tetrahydrofuran, N,
Amides such as N-dimethylformamide and N, N-dimethylacetamide; sulfur-containing compounds such as dimethylsulfoxide and sulfolane; nitromethane, nitroethane,
-Nitro compounds such as nitropropane, aliphatic nitriles such as acetonitrile, and mixtures thereof. After the completion of the reaction, a usual post-treatment as described below is performed to obtain a target compound. (1) The reaction solution is concentrated as it is, washed with water or (and) an organic solvent, and dried. (2) The reaction solution is poured into water, neutralized with saturated aqueous sodium hydrogen carbonate, extracted with an organic solvent, dried and concentrated. (3) The reaction solution is poured into water, and the precipitated crystals are collected by filtration and dried. The compound can also be purified by operations such as recrystallization and column chromatography.

The aniline compound represented by the general formula [III] is known in Japanese Patent Application Laid-Open Nos. 62-221677 and 62-158280, or
It can be manufactured according to the method described therein.

In the process for producing the amide compound represented by the general formula [II], depending on conditions, the general formula [II]
The amide compound represented by the general formula [II-1] [Wherein, R ¹ and Q represent the same meaning as described above. ] Or a hydrate of the amide compound represented by the general formula [II] and a hydrate thereof. Hydrates of the amide compound represented by the general formula [II-1] (hy
drate) can be used in the method for producing the compound of the present invention, similarly to the amide compound represented by the general formula [II].

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. Red-bellied weed: Oenother
a erythrosepala), Oenothera laciniata Ranunculaceae weeds: Togemino foxne button (Ranu)
nculus muricatus, Ibomi buttercup (Ranunculus sardous) Polygonaceae 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), Dutch Cerastium g
lomeratum) Acalyaceae Weed: Shiroza (Chenopodial al)
bum), Butterfly (Kochia scopari)
a) Amaranthaceae weed: Amaranthus r
etroflexus)
lanthus hybridus Brassicaceae Weed: Wild Radish (Raphan)
us raphanistrum)
inapis arvensis, Capsicum (Caps)
bur bursa-pastoris) and Mamegunbainazu (Lepidium virginicu)
m)

Legume Weeds: American Tsunoxanem (Se
sbania exaltata), lobster (Ca
ssia obtusifolia), Florida Vega
Weed (Desmodium torutuosu)
m), white clover (Trifomium repen)
s), Vicia sativ (Vicia sativ)
a), Clickago palm (Medicago lup)
ulina) 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), Dog Physalis (Sola)
num nigrum Scrophulariaceae Weed: Veronica
ca persica), Tachiinoufuguri (Vero)
nica arvensis)
onica hederaefolia Asteraceae Weed: Xanthium pensy
lvanicum), wild sunflower (Helianth)
us annuus), chamomile (Matricari)
a chamomilla), dog chamomile (Matr)
icaria performata or inodor
a), Common Mary Gold (Chrysanthem)
um segetum), savory ostrich (Matrica)
ria matricarioides, Ragweed (Ambrosia artemisiifoli)
a), Ambrosia trifid
a), Artemisia cana
densis), mugwort (Artemisia pri)
nceps), Solidago (Solidag)
o altissima), Dandelion (Tar)
axacum officinale Weaselaceae Weed: Forget-me-nots (Myosotis a)
Ravensis (Coleoptera: Chrysomelidae): Asclepias
syriaca spurges weed: Euphorbi
a helioscopia), Onishikisou (Eu)
phorbia maculata Anthracnoseaceae weed: American anthracite (Geranium)
carolinianum)

Oxalis weeds: Oxalis oxalis (Ox
aris corymbosa Cucurbitaceae Weeds: Arechiuri (Sicyos angula)
tus) 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)
opecurus geniculatus Cyperaceae Weed: Commelina co
mmunis) Rhododendron weeds: horsetail (Equisetum arve)
nse) Cyperaceae Weeds: Cygous cyperus (Cyperus)
ilia)
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), Sorghumcolor, soybean (Glycine max), cotton (Gossip)
ium spp. ), Sugar beet (Beta vulgar)
is), peanuts (Arachis hypogae)
a) 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,
In non-tillage cultivation of corn, wheat and the like, various weeds which are problematic 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) and fireflies (Sirpus j)
uncoides), pine trees (Eleocharis)
Acicularis) and Cyperus (Cyper)
us serotinus, Krogwai (Eleoc)
haris kuroguwai Water-lily Weeds: 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. Furthermore, the compound of the present invention can be used, for example, on a slope of a dike, a riverbed,
Road shoulders and slopes, railway floors, park green spaces, grounds,
Land for industrial facilities such as parking lots, airports, factories and storage facilities,
Non-agricultural land that needs to control the growth of weeds, such as fallow lands, or vacant lands in cities, or orchards, pastures,
A wide range of weeds generated on turf, forestry areas, etc. can be eliminated. In addition, the compound of the present invention can be used in a water hyacinth (Eichorniac) which is generated in rivers, waterways, canals, reservoirs and the like.
rassipes) and other herbicides.
The compound of the present invention is described in International Patent Application Publication Specification WO95 / 3.
Cultivate a crop having the same properties as the herbicidal compound described in JP-B-4659 and having been imparted with herbicide resistance by introducing a herbicide-resistance gene or the like described in the specification. In this situation, it is possible to use the compound of the present invention in a larger dose than that used for cultivation of a normal crop to which tolerance has not been imparted, and it is possible to herbicide other undesired plants 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 Examples thereof include fine powders of inorganic salts such as ammonium sulfate and the like and fine powders of synthetic silicon hydrate. Examples of the liquid carrier include:
Aromatic hydrocarbons such as alkylbenzene such as methylnaphthalene, phenylxylylethane and xylene, isopropanol, ethylene glycol, 2-ethoxyethanol
Alcohols such as chlorobenzene, 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, etc. include alkyl sulfates, alkyl sulfonates, alkyl aryl sulfonates, dialkyl sulfosuccinates, polyoxyethylene alkyl aryl ether phosphates. Anionic surfactants such as ester salts, polyoxyethylene alkyl ethers, polyoxyethylene alkyl aryl ethers, polyoxyethylene polyoxypropylene block copolymers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, etc. Nonionic surfactants and the like can be mentioned. Other pharmaceutical auxiliaries include lignin sulfonate, alginate, polyvinyl alcohol,
Gum arabic, CMC (carboxymethylcellulo-
And PAP (acidic isopropyl phosphate). 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. The soil treatment includes a soil surface treatment and a soil admixture treatment. The foliage treatment includes a treatment from above a plant body and a local treatment for treating only weeds so as not to adhere to crops. In addition, the use of a mixture with other herbicides may enhance the herbicidal efficacy. In addition, insecticides,
Miticides, nematicides, fungicides, plant growth regulators, fertilizers,
It can be mixed with or used in combination with a soil conditioner or the like.

Examples of such herbicides are shown below. Atrazine, cyanazine
ne), dimethametry (dimethametry)
n), metribuzin, promethrin, simazine
ine), simetryn, chlorotoluron, diuron (d)
iron), fluometuron
n), isoproturon,
Linuron, metabenzthiazuron, propanil, bentazone
ne), bromoxynil, ioxynil, pyridate (pyr)
idate) butamifos, dithiopyr (d
ithiopyr), etalfluralin (ethalf)
luralin), pendimesalin (pendime)
thalin), thiazopyr,
Trifluralin, acetochlor, arachlor (al
achlor, butachlor
r), diethatyl-ethyl
yl), dimethenamide (dimethenamide)
d), fluthiamide, mefenacet, metrachlor, pretilachlor (pr)
etilachlor), propachlor (propa)
chlor), cinmethililine (cinmethyli)
n) Acifluorfen, acifluorfen-Na salt (acifluorfen-so)
dim), benzfendizone
zone), bifenox, butafenacil, chlomethoxynil, fomesafen, lactofen
fen), oxadiazon, oxadiargyl, oxyfluorfen, carfentrazone-ethyl
l), fluazolate, fullmicrolacpentyl (flumiclorac-pe)
ntyl), flumioxazin (flumioxazi)
ne), fluthiacet methyl
-Methyl), isopropazole (isoprop)
azol), sulfentrazone (sulfentra)
zone), thidiazimine
n), azafenidin, pyraflufen-ethyl
l), sinidone-ethyl difenzoquat, diquat, paraquat
t)

2,4-D, 2,4-DB, clopyralid, dicamba
a), fluroxypyr, MC
PA, MCPB, mecoprop,
Quinclorac, triclopyr azimsulfuron, bensulfuron-meth
yl), chlorimuron ethyl
-Ethyl), chlorsulfuron (chlorsul)
furon), cloranslam methyl (clorans)
ulam-methyl), cyclosulfamuron (c
iclosulfamuron, dicloslam (di)
Closlam), ethoxysulfuron (ethox)
ysulfuron), flazasulfuron (flaza)
sulfuron), flucarbazone (flucarb)
azone), flumetsura (flumetsula)
m), flupyrsulfur (flupyrsulfur)
on), halosulfuron methyl (halosulfur)
on-methyl), imazosulfuron (imazo)
sulfuron), iodosulfuron (iodos)
ulfuron), metosura (methosula)
m), metsulfuron-methyl (metsulfuron-
methyl), nicosulfuron (nicosulfu)
ron), oxasulfuron
n), primisulfuron methyl (primisulfu)
ron-methyl), procarbazone Na salt (pr
ocarbazone-sodium, prosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron-methyl
l), sulfosulfuron (sulfosulfuron)
n), triasulfuron
n), tribenuron-methyl (tribenuron-
methyl), tritosulfuron (tritosul)
furon), thifensulfuron-methyl (this)
nsulfuron-methyl, triflusulfuron-methyl
yl), pyribenzonoxi
m), bispyribac-Na salt (bispyribac-
sodium, pyriminobac-methyl (pyrimi)
nobac-methyl, pyrithiobac-sodium, imazameth, imazamethabenz-methyl, imazamox, imazapic (i)
mazapic), imazapyr (imazapyr),
Imazaquin (imazaquin), imazethapyr (i
mazethapyr) Tepraloxydim, alloxydim-Na salt (alloxydim-sodiu)
m), clethodim, clodinahop-propargyl (clodinafop-prop)
argyl), cyhalofobutyl (cyhalofo)
p-butyl, diclohopmethyl (diclof)
op-methyl), fenoxaprop-ethyl, fenoxaprop-ethyl (fenoxaprop-p-et)
hyl), fluazifop butyl (fluazifop)
-Butyl), fluazifop-p-butyl (fl
uazipop-p-butyl, haloxyfop-methyl, quizalofop-p-ethyl (quizalofop-p-eth)
yl), sethoxydim, traloxydim diflufenican, flurtamone, norflurazone, benzophenap (b)
enzofenap), isoxaflutole (isox)
aflutole, pyrazolate
te), pyrazoxyfen
n), sulcotrione, clomazone, mesotrione (me)
sotrione), isoxachlortol (isox)
achlortole)

Bialaphos, glufosinate ammonium salt (glufosinat)
e-ammonium), glyphosate (glyph)
Osate, sulfosate dichlobenil, isoxaben, benthiocarb
iocarb), butyrate, dimepiperate, EPT
C, esprocarb, moline-
(Molinate), piribuchi carba (pyrib)
uticarb), triallat (triallat)
e) diflufenzopyr bromobutide, DSMA,
MSMA, cafenstrol
l), daimuron, epoprodan, flupoxam (flupox)
am), metobenzuron
n), pentoxazone, piperophos, triaziflam, beflubutamide, benzobicyclone, benzobifenclos, clomeprop, clomepropane, clomeprop, clomepropane, clomeprop, clomeprop, framezap, clomeprop, framezap, clomeprop, framezap, clomeprop, framez, clomeprop) flora
sulam), indanofan (indanofa)
n), isoxadifen, mesotrione, naproanilide, oxaziclomefone, pesoxyamide, phenothiol
nothiol), pyridafor (pyridafo)
l)

The above compounds are described in Farm Chemicals Handbook (Meister Publishing Company) [Far
m Chemical Handbook (Meiste
r Publishing Company) 1995
Annual version of the catalog, Agchem New Compound Review 1995 (Agchem Information Service)
[AG CHEM NEW COMPOUND REVIE
W, VOL. 13, 1995 (AG CHEM INF
ORMATION SERVICE)], Agchem New Compound Review 1997 Edition (Agchem Information Service) [AG CHEM NEW COM
POUND REVIEW, VOL. 15, 1997
(AG CHEM INFORMATION SERVI
CE)], Agchemnu-Compound Review-199
Eighth Edition (Agchem Information Service) [AG
CHEM NEW COMPOUND REVIEW, V
OL. 16, 1998 (AG CHEM INFORMA
AG SERVICE)], Agchem New Compound Review 1999 Edition (Agchem Information Service) [AG CHEM NEW COMPOUN]
D REVIEW, VOL. 17, 1999 (AG CH
EM INFORMATION SERVICE)] or "Herbicide Research Directory (Hakutosha)".

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 0.01 g-20 per
000 g, preferably 1 g to 12000 g. Emulsions, wettable powders, suspensions, thick emulsions, wettable powders and the like are usually prepared in an amount of 10 to 1000 liters per hectare (if necessary). The treatment is carried out by diluting with water (to which an auxiliary agent such as a spreading agent is added), and the granules and certain suspending agents are usually treated without dilution. Here, as an auxiliary used as needed, in addition to the above-mentioned surfactant, polyoxyethylene resin acid (ester),
Vegetable oils such as ligninsulfonate, abietate, dinaphthylmethanedisulfonate, crop oil concentrate, soybean oil, corn oil, cottonseed oil, sunflower oil and the like. The compound of the present invention may also 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 foliage treatment is carried out alone or in combination with another harvesting aid before harvesting the crop.

[0054]

EXAMPLES The present invention will be described in more detail with reference to the following Examples, but it should not be construed that the present invention is limited thereto. First, Production Examples of the compound of the present invention will be described. The compound numbers assigned to the compounds of the present invention are the compound numbers described in Tables 1 to 10 below.

Production Example 1 In 150 ml of toluene, 33.0 g of compound [1a] and 4,
Ethyl 4,4-trifluoroacetoacetate (30.3 g) was added, and the mixture was stirred under heating and reflux for 4 hours. Thereafter, the reaction solution was concentrated under reduced pressure, and the obtained residue was dissolved in ethyl acetate.The ethyl acetate solution was washed with concentrated hydrochloric acid, further washed with water, and dried over anhydrous magnesium sulfate. Then, the mixture was concentrated under reduced pressure to obtain 35.7 g of the compound [2a]. Compound [2a] Melting point: 110.4 ° C

7.16 g of compound [2a] in 30 ml of acetic acid
And 1.8 g of potassium cyanate were added, and the mixture was stirred at room temperature overnight (about 12 hours). Thereafter, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give 7.17 g of compound [3a] (compound 3-3 of the present invention). Compound [3a] (Compound 3-3 of the present invention) ¹ H-NMR (300 MHz, CDCl ₃ , TMSδ (ppm)) 2.26 to 2.30 (1H, m),
2.32 ~ 2.53 (1H, br), 3.08 ~ 3.26 (2H, m), 4.59 ~ 4.69 (4H,
m), 6.78 to 6.88 (1H, br), 6.85 to 6.90 (1H, m), 6.99 to 7.02 (1
H, m,)

Production Example 2 To a solution of 3.56 g of the compound [1b] in 14.5 ml of acetic acid was added 1.04 g of sodium cyanate at room temperature, and the mixture was stirred at the same temperature for 2.5 hours. Thereafter, water was added to the reaction solution, and extracted with ethyl acetate. The organic layer was washed with an aqueous sodium hydroxide solution and washed with a saturated saline solution. The organic layer was dried over magnesium sulfate, and the residue obtained after concentration was subjected to column chromatography (hexane: ethyl acetate = 4: 1 to 2:
Compound [2b] (Compound 5-25 of the present invention)
3.72 g were obtained. Compound [2b] (Compound 5-25 of the present invention) ¹ H-NMR (300 MHz, CDCl ₃ , TMS δ (ppm)) 1.18 to 1.28 (3H,
m), 1.62 to 1.67 (1H, m), 2.97 to 3.21 (2H, m), 4.08 to 4.24 (2
H, m), 4.65-4.72 (1H, m), 6.74-6.85 (1H, m), 6.89-7.08
(1H, br), 7.26 (1H, d, J = 7.42Hz)

Production Example 3 0.79 g of potassium cyanate was added to a solution of 2.72 g of the compound [1c] in 10 ml of acetic acid at room temperature, followed by stirring at the same temperature for 2 hours. Thereafter, the reaction solution was concentrated, water and hexane were added, and the mixture was allowed to stand. The resulting crystals were filtered, washed with water and then with hexane, and dried to obtain 2.73 g of compound [2c] (compound 5-68 of the present invention). Compound [2c] (Compound 5-68 of the present invention) Melting point 100.2 ° C. ¹ H-NMR (300 MHz, CDCl ₃ , TMS δ (ppm)) 1.40 (3H, t, J = 7.1)
1Hz), 3.06-3.24 (2H, m), 4.30-4.38 (2H, m), 7.16-7.22 (1H,
m), 7.35 (1H, d, J = 8.69Hz)

Production Example 4 To a solution of 2.50 g of the compound [1d] in 10 ml of acetic acid was added 0.70 g of potassium cyanate at room temperature, and the mixture was stirred at the same temperature for 2 hours. Thereafter, the reaction solution was concentrated, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate and saturated saline. After drying over magnesium sulfate and concentrating, the residue obtained is subjected to column chromatography (hexane:
Ethyl acetate = 3: 1 to 1: 1) to give compound [2d]
2.68 g of (the present compound 5-71) was obtained. Compound [2d] (Compound 5-71 of the present invention) [ ¹ H-NMR (300 MHz, CDCl ₃ , TMSδ (ppm)) 3.06-3.24 (2H,
m), 3.63-3.69 (5H, m), 7.05-7.20 (1H, br), 7.29 (1H, d, J = 8.
97Hz), 7.36-7.44 (1H, m))

Production Example 5 To a solution of 2.65 g of the compound [1e] in 10 ml of acetic acid was added 0.78 g of potassium cyanate at room temperature, and then 10.10 g of the compound [1e] was added at the same temperature.
Stir for 5 hours. Thereafter, the reaction solution was concentrated, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate and saturated saline. The crystals obtained after drying over magnesium sulfate and concentrating were washed with hexane to give compound [2e].
2.61 g of (the present compound 6-5) was obtained. Compound [2e] (Compound 6-5 of the present invention) Melting point 151.1 ° C. ¹ H-NMR (300 MHz, CDCl ₃ , TMSδ (ppm)) 1.35-1.40 (6H,
m), 3.13-3.27 (2H, m), 5.18-5.32 (1H, m), 7.34 (1H, d, J = 10.
9Hz), 7.78 (1H, d, J = 9.30Hz)

Production Example 6 To a solution of 2.68 g of the compound [1f] in 10 ml of acetic acid was added 0.75 g of potassium cyanate at room temperature, and the mixture was treated at the same temperature with 3.5 g.
Stirred for hours. Thereafter, the reaction solution was concentrated, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate and saturated saline. After drying over magnesium sulfate and concentration, column chromatography (hexane: ethyl acetate =
3: 1 to 1: 1) to give 2.84 g of compound [2f] (Compound 5-24 of the present invention). Compound [2f] (Compound 5-24 of the present invention) ¹ H-NMR (300 MHz, CDCl ₃ , TMS δ (ppm)) 1.64-1.68 (3H,
m), 3.00-3.16 (2H, m), 3.72-3.75 (3H, m), 4.67-4.74 (1H,
m), 6.73-6.84 (1H, m), 6.84-7.10 (1H, br), 7.28 (1H, d, J = 9.
17Hz)

Production Example 7 0.89 g of potassium cyanate was added to a solution of 2.87 g of the compound [1 g] in 12 ml of acetic acid at room temperature, and then 4.5 g at the same temperature.
Stirred for hours. Thereafter, the reaction solution was concentrated, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate and saturated saline. The crystals obtained after drying over magnesium sulfate and concentrating were washed with hexane to give the compound [2 g].
3.14 g of the present compound 3-16 was obtained. Compound [2 g] (Compound 3-16 of the present invention) Melting point 152.7 ° C. ¹ H-NMR (300 MHz, CDCl ₃ , TMS δ (ppm)) 1.56 (6H, d, J = 6.9)
2Hz), 3.14-3.33 (2H, m), 4.60-4.72 (1H, m), 6.78-6.86 (1H,
m), 6.99-7.03 (1H, m), 7.31 (1H, d, J = 8.48Hz)

Production Example 8 To a solution of 2.51 g of the compound [1h] in 10 ml of acetic acid was added 0.80 g of potassium cyanate at room temperature, and the mixture was added at the same temperature.
Stir for 5 hours. Thereafter, the reaction solution was concentrated, and the obtained crystals were washed with hexane to obtain 2.25 g of compound [2h] (Compound 5-14 of the present invention). Compound [2h] (Compound 5-14 of the present invention) Melting point 151.9 ° C. ¹ H-NMR (300 MHz, CDCl ₃ , TMSδ (ppm)) 2.57 (1H, s), 3.09
-3.29 (2H, m), 4.72-4.75 (2H, m), 6.65 (1H, br), 6.92-6.96
(1H, m), 7.29 (1H, d, J = 8.68Hz)

Some of the compounds of the present invention that can be produced according to the methods described in Production Methods 1 to 8 are listed below, but the present invention is not limited thereto. In the table, Me
= Methyl group, Et = ethyl group, Pr = propyl group, i-
Pro = isopropyl group, Bu = butyl group, i-Bu =
Isobutyl group, Pen = pentyl group, Hex = hexyl group.

Compound represented by general formula [I-1]

[Table 1]

Compound represented by general formula [I-2]

[Table 2]

Compound represented by general formula [I-3]

[Table 3]

Compound represented by general formula [I-4]

[Table 4]

Compound represented by general formula [I-5]

[0070]

[Table 5]

[Table 6]

[Table 7] Compound represented by general formula [I-6]

[Table 8]

Compound represented by general formula [I-7]

[Table 9]

Compound represented by general formula [I-8]

[Table 10]

Next, preparation examples will be shown. In addition, this invention compound is shown by the compound number of Table 1-Table 10. Parts are parts by weight. Formulation Example 1 50 of each of the present compounds 3-3, 3-16 and 6-5
Parts, 3 parts of calcium ligninsulfonate, 2 parts of sodium lauryl sulfate and 45 parts of synthetic hydrous silicon oxide are crushed and mixed well to obtain each wettable powder. Formulation Example 2 10 of each of the present compounds 3-3, 3-16 and 6-5
Part, polyoxyethylene styrylphenyl ether 14
, 6 parts of calcium dodecylbenzenesulfonate, 35 parts of xylene and 35 parts of cyclohexanone are mixed well to obtain each emulsion. Formulation Example 3 Each of Compounds 3-3, 3-16 and 6-5 of the Present Invention 2
Parts, 2 parts of synthetic hydrous silicon oxide, 2 parts of calcium ligninsulfonate, 30 parts of bentonite and Kaolin Kure-6
4 parts are crushed and mixed well, water is added and kneaded well,
After granulation and drying, each granule is obtained. Formulation Example 4 25 of each of the present compounds 3-3, 3-16 and 6-5
Part, polyvinyl alcohol 10% aqueous solution 50 parts, water 25
Parts were mixed and wet-pulverized until the average particle size became 5 micrometers or less to obtain each suspending agent. Formulation Example 5 To 40 parts of a 10% aqueous solution of polyvinyl alcohol, 5 parts of each of the compounds of the present invention 3-3, 3-16 and 6-5 is added, and the average particle size is reduced to 10 μm or less by a homogenizer. Emulsified and dispersed to the extent necessary, and then 55 parts of water were added to obtain each concentrated emulsion.

Next, Test Examples show that the compound of the present invention is useful as an active ingredient of a herbicide. The results of the herbicidal activity test were visually determined in 11 stages from 10 (complete death or complete germination inhibition) to 0 (no effect), and 7 or more were judged to be effective. The compounds of the present invention are listed in Tables 1 to 1.
It is indicated by a compound number of 0. Test Example 1 Field foliage treatment test A cylindrical plastic pot having a diameter of 10 cm and a depth of 10 cm was filled with soil, American morning glory was sown, and grown in a greenhouse for 14 days. Thereafter, each of the present compounds 3-3, 3-16 and 6-5 was made into an emulsion according to Formulation Example 2,
The predetermined amount was diluted with water containing a spreading agent equivalent to 1000 liters per hectare, and the whole foliage was uniformly treated from above the plant with a sprayer. After the treatment, the plants were grown in a greenhouse for 12 days, and the herbicidal efficacy was examined. As a result, all of the compounds 3-3, 3-16 and 6-5 of the present invention showed effective activity against morning glory at a dose of 20 g / a. Test Example 2 Upland soil surface treatment test Soil was packed in a cylindrical plastic pot having a diameter of 10 cm and a depth of 10 cm, and American morning glory was sown. According to Formulation Example 2, each of the present compounds 3-3 and 3-16 was made into an emulsion, a predetermined amount of which was diluted with water equivalent to 1000 liters per hectare, and uniformly sprayed on the entire surface of the soil with a sprayer. The plants were raised in a greenhouse 12 days after the treatment, and the herbicidal efficacy was examined. As a result, Compounds 3-3 and 3-16 of the present invention effectively inhibited the emergence of American morning glory at a dose of 80 g / a.

[0075]

By using the compound of 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 43/84 102 A01N 43/84 102 C07D 405/04 C07D 405/04 413/04 413/04 417/04 417/04 F term (reference) 4C063 AA01 BB01 CC54 CC62 DD29 EE03 4H011 AB01 BB08 BB09 BB10 BC01 BC03 BC05 BC07 BC18 BC19 BC20 DA02 DA13 DA15 DA16 DC03 DC05 DC06 DC08 DD03 DD04 DH02 DH03 DH10

Claims (4)

[Claims] 1. A compound of the general formula [I] [Wherein, R ¹ represents a C1-C2 haloalkyl group, and Q represents any one of Q1 to Q8 represented by the following general formula. Wherein, R ³ represents a hydrogen atom or a halogen atom, R ⁴
Represents a hydrogen atom, a halogen atom, a cyano group, a nitro group or an ethynyl group, or has the general formula Wherein R ⁵ represents a hydrogen atom, a C1-C6 alkyl group, a halogen atom, a cyano group, a nitro group, or a hydroxyl group, and R ⁶ represents a C1-C6 alkyl group, a C1-C6
6 haloalkyl group, C3-C8 cycloalkyl group, C3
-C8 cycloalkyl C1-C3 alkyl group, C3-C
6 alkenyl group, C3-C6 alkynyl group, cyano C1
-C3 alkyl group, C1-C3 alkoxy C1-C3 alkyl group, C1-C3 alkylthio C1-C3 alkyl group, C1-C6 alkylcarbonyl group, C1-C6 haloalkylcarbonyl group, C3-C8 cycloalkylcarbonyl group, carboxy C1- C3 alkyl group, C1-C
6 alkoxycarbonyl C1-C3 alkyl group, C1-
A C6 haloalkoxycarbonyl C1-C3 alkyl group,
C3-C8 cycloalkoxycarbonyl C1-C3 alkyl group, C3-6 alkenyloxycarbonyl C1-C
3 alkyl groups, C3-C6 alkynyloxycarbonyl C1-C3 alkyl groups, C1-C3 alkoxy C1-C
3 alkoxycarbonyl C1-C3 alkyl group, carboxy C1-C3 alkoxycarbonyl C1-C3 alkyl group, C1-C6 alkoxycarbonyl C1-C3 alkoxycarbonyl C1-C3 alkyl group, C1-C6 haloalkoxycarbonyl C1-C3 alkoxycarbonyl C1- C3 alkyl group, C3-C6 alkenyloxycarbonyl C1-C3 alkoxycarbonyl C1-C3
Alkyl group, C3-C6 alkynyloxycarbonyl C
A 1-C3 alkoxycarbonyl C1-C3 alkyl group,
A C3-C8 cycloalkoxycarbonyl C1-C3 alkoxycarbonyl C1-C3 alkyl group, an optionally substituted aryloxycarbonyl C1-C3 alkyl group, an optionally substituted aryl C1-C3 alkoxycarbonyl C1-C3 alkyl group or Represents a C1-C6 alkoxycarbonyl group or a compound of the general formula -SO
₂ R ¹⁷ , -C (R ²⁸ ) R ²⁹ CON (R ²¹ ) R ²² , -C
^{(R 30) R 31 COON (} R 23) R 24, Or R ⁷ represents a hydrogen atom, a C1-6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a hydroxy group, a C1-C6 alkoxy group, a C
1-C6 haloalkoxy group, C3-C8 cycloalkoxy group, C3-C6 alkenyloxy group, C3-C6 alkynyloxy group, C1-C3 alkoxy C1-C3 alkoxy group, carboxy C1-C3 alkoxy group, C1-
C6 alkoxycarbonyl C1-C3 alkoxy group, C
3-C8 cycloalkoxycarbonyl C1-C3 alkoxy group, C3-C6 alkenyloxycarbonyl C1-
C3 alkoxy, C3-C6 alkynyloxycarbonyl C1-C3 alkoxy group, or represents an optionally substituted phenoxy group or an optionally substituted benzyloxy group, or the general formula -N (R ²¹⁾ R ²² or −
ON (R ²³ ) represents a group represented by R ²⁴ , wherein R ⁸ is a hydroxy group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, a C3-C6 alkenyloxy group, a C3-C6 Alkynyloxy group, C
1-C3 alkoxy represents a C1-C3 alkoxy group, an optionally substituted phenoxy group or an optionally substituted benzyloxy group, or a compound represented by the general formula -N
(R ²¹ ) represents a group represented by R ²² or —ON (R ²³ ) R ²⁴ ; R ⁹ represents a hydrogen atom or a halogen atom;
¹⁰ is a hydroxy group, a C1-C6 alkoxy group, a C1-C
6 haloalkoxy group, C3-C8 cycloalkoxy group,
Represents a C3-C6 alkenyloxy group, a C3-C6 alkynyloxy group, a C1-C3 alkoxy C1-C3 alkoxy group, an optionally substituted phenoxy group or an optionally substituted benzyloxy group, or a compound represented by the general formula- N (R ²¹ ) R ²² or —ON (R ²³ ) R ²⁴ represents a group represented by R ¹¹ represents a hydrogen atom or a halogen atom, and R ¹² represents a hydrogen atom, a formyl group, a cyano group, a nitro group, an amino group; Group, C1-C6 alkyl group, C1-C6 haloalkyl group, hydroxy C1-C3 alkyl group, C1-
C3 alkoxy C1-C3 alkyl group, C1-C6 alkylcarbonyloxy C1-C3 alkyl group, C1-C3
6-haloalkylcarbonyloxy C1-C3 alkyl group, carboxy group, C1-C6 alkoxycarbonyl group, C1-C6 haloalkoxycarbonyl group, C3-C
Represents an 8-cycloalkoxycarbonyl group, a C3-C6 alkenyloxycarbonyl group, a C3-C6 alkynyloxycarbonyl group or a C1-C3 alkoxy C1-C3 alkoxycarbonyl group, and R ¹³ represents a hydrogen atom or C1
R ¹⁴ represents a hydrogen atom, C 1 -C 6
Alkyl group, C1-C6 haloalkyl group, hydroxy C
1-C3 alkyl group, C1-C3 alkoxy C1-C3
Alkyl group, C1-C6 alkylcarbonyloxy C1
-C3 alkyl group, C1-C6 haloalkylcarbonyloxy C1-C3 alkyl group, carboxy group, C1-C
6-alkoxycarbonyl group, C1-C6 haloalkoxycarbonyl group, C3-C8 cycloalkoxycarbonyl group, C3-C6 alkenyloxycarbonyl group, C3-
Represents a C6 alkynyloxycarbonyl group or a C1-C3 alkoxy C1-C3 alkoxycarbonyl group,
¹⁵ is a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 cycloalkyl C1-C3 alkyl group, a C3-C6 alkenyl group, a C3-C6 alkynyl group, a cyano C1-C3 alkyl group A C1-C3 alkoxy C1-C3 alkyl group, C
1-C3 alkylthio C1-C3 alkyl group, C1-C
6 alkylcarbonyl group, C1-C6 haloalkylcarbonyl group, C3-C8 cycloalkylcarbonyl group, carboxy C1-C3 alkyl group, C1-C6 alkoxycarbonyl C1-C3 alkyl group, C1-C6 haloalkoxycarbonyl C1-C3 alkyl group, C3-C8 cycloalkoxycarbonyl C1-C3 alkyl group, C3
-6 alkenyloxycarbonyl C1-C3 alkyl group, C3-C6 alkynyloxycarbonyl C1-C3
Alkyl group, C1-C3 alkoxy C1-C3 alkoxycarbonyl C1-C3 alkyl group, carboxy C1-
C3 alkoxycarbonyl C1-C3 alkyl group, C1
-C6 alkoxycarbonyl C1-C3 alkoxycarbonyl C1-C3 alkyl group, C1-C6 haloalkoxycarbonyl C1-C3 alkoxycarbonyl C1-C
3 alkyl groups, C3-C8 cycloalkoxycarbonyl C1-C3 alkoxycarbonyl C1-C3 alkyl groups, C3-C6 alkenyloxycarbonyl C1-C3
Alkoxycarbonyl C1-C3 alkyl group, C3-C
6 alkynyloxycarbonyl C1-C3 alkoxycarbonyl C1-C3 alkyl group, optionally substituted aryloxycarbonyl C1-C3 alkyl group, optionally substituted aryl C1-C3 alkyloxycarbonyl C1-C3 alkyl group or C1 Represents a -C6 alkoxycarbonyl group, or a general formula And Z represents an oxygen atom, a sulfur atom or N
H represents a group, and T represents a direct bond or a methylene group. <Here, R ¹⁷ is a C1-C3 alkyl group or a C1-C3
Represents a 3 haloalkyl group, R ¹⁸ is a hydrogen atom, C1-C3
Represents an alkyl group or a C1-C6 alkoxycarbonyl group, and R ¹⁹ is a hydrogen atom, a halogen atom, a nitro group, a hydroxy group, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy. Group, C3-C8 cycloalkoxy group, C3-C6
Alkenyloxy group, C3-C6 alkynyloxy group,
Carboxy C1-C3 alkoxy group, C1-C6 alkoxycarbonyl C1-C3 alkoxy group, C3-C8 cycloalkoxycarbonyl C1-C3 alkoxy group, C
3-C6 alkenyloxycarbonyl C1-C3 alkoxy group or C3-C6 alkynyloxycarbonyl C
Represents a 1-C3 alkoxy group, and R ²⁰ represents a hydrogen atom, a halogen atom, a nitro group, a hydroxy group, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3- C8 cycloalkoxy group, C3-C6 alkenyloxy group, C3-C
6 alkynyloxy group, carboxy C1-C3 alkoxy group, C1-C6 alkoxycarbonyl C1-C3 alkoxy group, C3-C8 cycloalkoxycarbonyl C1
-C3 alkoxy group, C3-C6 alkenyloxycarbonyl C1-C3 alkoxy group or C3-C6 alkynyloxycarbonyl C1-C3 alkoxy group,
R ²¹ and R ²² independently represent a hydrogen atom or a C1-C3 alkyl group, or are bonded at the terminal to form a C2-C5
Alkylene group or C1-C3 alkyleneoxy C1-
R ²³ and R ²⁴ independently represent a hydrogen atom or a C1-C3 alkyl group, or are bonded at the terminal to form a C2-C5 alkylene group or a C1-C3 alkylene group;
3 alkyleneoxy C1-C3 alkylene group;
²⁵ is a hydrogen atom, a C1-C3 alkyl group or a C1-C6
R ²⁶ represents a hydrogen atom, a halogen atom, a nitro group, a hydroxy group, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkyl group; An alkoxy group, a C3-C6 alkenyloxy group, a C3-
C6 alkynyloxy group, carboxy C1-C3 alkoxy group, C1-C6 alkoxycarbonyl C1-C3 alkoxy group, C3-C8 cycloalkoxycarbonyl C
Represents a 1-C3 alkoxy group, a C3-C6 alkenyloxycarbonyl C1-C3 alkoxy group or a C3-C6 alkynyloxycarbonyl C1-C3 alkoxy group, and R ²⁷ represents a hydrogen atom, a halogen atom, a nitro group, a hydroxy group, a C1-C6 Alkyl group, C1-C6 haloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group, C3-C6 alkenyloxy group, C3-C6 alkynyloxy group, carboxy C1-C3 alkoxy group, C1-C6 alkoxycarbonyl C1-C3 alkoxy group, C3-C8 cycloalkoxycarbonyl C1-C3 alkoxy group, C3
-C6 alkenyloxycarbonyl C1-C3 alkoxy group or C3-C6 alkynyloxycarbonyl C1
R ²⁸ represents a hydrogen atom or C1
R ²⁹ represents a hydrogen atom or C1-
Represents a C3 alkyl group, and R ³⁰ is a hydrogen atom or C1-C
R ³¹ represents a hydrogen atom or C1-C3
R ³² , R ³³ and R ³⁴ are the same or different and each represent a hydrogen atom, a halogen atom, C1-C3
Alkyl group, C1-C3 haloalkyl group, nitro group, amino group, OH group, SH group, cyano group, carboxy group, C
1-C6 alkoxycarbonyl group, C3-C8 cycloalkoxycarbonyl group, C3-C6 alkenyloxycarbonyl group, C3-C6 alkynyloxycarbonyl group, carboxy C1-C3 alkyl group, C1-C6 alkoxycarbonyl C1-C3 alkyl group, C3 -C8 cycloalkoxycarbonyl C1-C3 alkyl group, C3
-C6 alkenyloxycarbonyl C1-C3 alkyl group, C3-C6 alkynyloxycarbonyl C1-C3
Alkyl group, carboxy C1-C3 alkoxy group, C1
-C6 alkoxycarbonyl C1-C3 alkoxy group,
C3-C8 cycloalkoxycarbonyl C1-C3 alkoxy group, C3-C6 alkenyloxycarbonyl C1
-C3 alkoxy group, C3-C6 alkynyloxycarbonyl C1-C3 alkoxy group, carboxy C1-C3
Alkylthio group, C1-C6 alkoxycarbonyl C1
-C3 alkylthio group, C3-C8 cycloalkoxycarbonyl C1-C3 alkylthio group, C3-C6 alkenyloxycarbonyl C1-C3 alkylthio group, C
3-C6 alkynyloxycarbonyl C1-C3 alkylthio group, carboxy C1-C3 alkylamino group, C
1-C6 alkoxycarbonyl C1-C3 alkylamino group, C3-C8 cycloalkoxycarbonyl C1-
A C3 alkylamino group, a C3-C6 alkenyloxycarbonyl C1-C3 alkylamino group, a C3-C6 alkynyloxycarbonyl C1-C3 alkylamino group,
C1-C6 alkoxy group, C3-C6 alkenyloxy group, C3-C6 alkynyloxy group, C1-C6 alkylcarbonyloxy group, C1-C6 alkoxycarbonyloxy group, C1-C6 alkylthio group, C3-C6 alkenylthio group, C3 -C6 alkynylthio group, C1-
C6 alkylcarbonylthio group, C1-C6 alkoxycarbonylthio group, C1-C6 alkylamino group, C3
-C6 alkenylamino group, C3-C6 alkynylamino group, C1-C6 alkylcarbonylamino group or C
Represents a 1-C6 alkoxycarbonylamino group. 〉]]
A 5,6-dihydrouracil compound represented by the formula: 2. The compound according to claim 1, wherein Q is Q1
A 5,6-dihydrouracil compound which is a group represented by the formula: 3. The compound according to claim 1, wherein Q is Q
5,6-dihydrouracil compound which is a group represented by 4, Q5, Q6, Q7 or Q8. 4. A herbicide comprising the 5,6-dihydrouracil compound according to claim 1 or 2 as an active ingredient.