JPH11140054A - 2-pyridone derivative and herbicide - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a new compound capable of withering only weeds without giving damage of crops and useful as a herbicide capable of providing perfect effect at a low dosage. SOLUTION: This compound is represented by formula I[R<1> is H, a (halo) alkyl, acetyl or the like; R<2> is a haloalkyl; R<3> is H, an alkyl, COOH or the like; R<4> is H, a halogen, cyano or the like; Q is a group of formula II (R<5> is H or a halogen; R<6> is H, nitro or the like; R<11> is H, or the like) or the like, e.g. 3-(4-chloro-2-fluoro-5-acetonyloxyphenyl)-1-methyl-6-trifluoromethyl-2 (1H)- pyrrolidone. The compound of formula I is produced by a method, e.g. reacting a compound of formula; NCCH2 -Q" (Q" is Q) with a compound of formula III (Et is ethyl) in the presence of a base, treating the reaction product with an acid to provide a mixture of compound or the like of formula IV and reacting the compound of formula IV with 2,4-dinitrophenoxyamine or the like in the presence of a base or the like to provide a compound of formula V.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a 2-pyridone derivative and a herbicide containing the same as an active ingredient.

[0002]

2. Description of the Related Art Hitherto, 3- (substituted) phenyl-
Some 2-pyridone derivatives are known, but a 3- (substituted) phenyl-6-haloalkyl-2-pyridone derivative which is a feature of the compound of the present invention is not known.
For example, Japanese Patent Publication No. 46-30190 discloses 3-
(4-Chlorophenyl) -6-methyl-2-pyridone has been described. Also, United States Patent US-37
No. 20768 describes 3-phenyl-6-ethyl-2-pyridone. However, none of the specifications describe the herbicidal activity of the compound.

[0003]

In recent years, there has been a strong demand for a herbicide having a selective action of killing only weeds without damaging the crops, even when applied to useful crops and weeds at the same time. . In addition, in order to prevent the drug from remaining excessively in the environment, it is desired to develop a drug capable of obtaining a complete effect at a low dose. An object of the present invention is to provide a new herbicide satisfying these needs.

[0004]

Means for Solving the Problems In order to solve the above-mentioned problems, the present inventors have synthesized a large number of pyridone derivatives and have studied variously their usefulness. As a result, they have found that certain 2-pyridone derivatives have excellent herbicidal activity and selectivity that solve the above problems, and have completed the present invention. That is, the present invention relates to (1) a compound represented by the general formula [I]:

[0005]

Embedded image In the formula, R ¹ is a hydrogen atom, an alkyl group, a haloalkyl group, an acetyl group, a group —N ＝ CR ¹² R ¹³ or a group —NR
¹⁷ R ¹⁸ , wherein R ¹² and R ¹³ are each independently a hydrogen atom, an alkyl group, a group —NR ¹⁷ R ¹⁸ or a phenyl group (the group is substituted with a halogen atom, a nitro group, an alkyl group, a haloalkyl group or an alkoxy group) R ¹⁷ and R ¹⁸ each independently represent a hydrogen atom, an alkyl group, a haloalkyl group, an acyl group, an alkoxycarbonyl group, a benzoyl group (the group is a halogen atom, a nitro group, an alkyl group, A haloalkyl group or an alkoxy group; a phenoxycarbonyl group (the group may be substituted with a halogen atom, a nitro group, an alkyl group, a haloalkyl group or an alkoxy group), a formyl group or an alkyl group; Represents a sulfonyl group. R ² represents a haloalkyl group; R ³ represents a hydrogen atom, an alkyl group, a carboxyl group or an alkoxycarbonyl group; R ⁴ represents a hydrogen atom, a halogen atom, an alkoxy group, a cyano group or an alkyl group;

[0006]

Embedded image Wherein, ^{R 5} represents a hydrogen atom or a halogen atom, ^{R 6}
Represents a hydrogen atom, a halogen atom, a nitro group or a cyano group, R ⁷ represents an acylalkoxy group, a dialkoxyalkoxy group, a dialkoxyalkylthio group, a hydroxycycloalkyloxy group, an alkoxycycloalkyloxy group, an acyloxycycloalkyloxy group, Alkoxycarbonyloxycycloalkyloxy group, cycloalkenyloxy group, acylamino group, dialkoxycarbonylalkylthio group, dialkoxycarbonylalkoxy group, dialkoxyphosphonylalkyl group, epoxycycloalkyl group, (alkenyloxy group, alkylsulfonyloxy group or A cycloalkyl group substituted with an alkyl group) or a general formula

[0007]

Embedded image Represents a group represented by the formula, Y is an oxygen atom, a sulfur atom or a group -NR ^17, Het is 3- to 6-membered heterocyclic ring (in which a halogen atom, a nitro group, an oxo group, an alkyl group, R ¹⁴ represents a hydrogen atom, an alkyl group or a cycloalkyl group, R ¹⁵ represents an alkoxyalkoxyalkyl group, an alkoxycarbonylalkyl group,
Alkenyloxycarbonylalkyl group, alkynyloxycarbonylalkyl group, cycloalkyloxycarbonylalkyl group, alkoxyalkoxycarbonylalkyl group, haloalkoxycarbonylalkyl group, haloalkenyloxycarbonylalkyl group, benzyloxycarbonylalkyl group (the benzyl group of the group is May be substituted with a halogen atom, nitro group, alkyl group, haloalkyl group or alkoxy group.), Alkylthiocarbonylalkyl group, alkylsulfinylalkoxycarbonylalkyl group, alkylsulfonylalkoxycarbonylalkyl group, monoalkylcarbamoylalkyl group, dialkyl Carbamoylalkyl group, alkylthioalkoxycarbonylalkyl group, phenoxycarbonylalkyl Group (the phenyl group of the group are a halogen atom, a nitro group, an alkyl group, optionally substituted haloalkyl group or alkoxy group.), Alkoxycarbonyl alkoxycarbonylalkyl radical, R
²⁰ represents a hydrogen atom, a halogen atom or an alkyl group.
R ⁸ represents a hydrogen atom, a halogen atom, a hydroxyl group, an alkoxy group, an alkenyloxy group, an alkynyloxy group,
Haloalkoxy groups, haloalkenyloxy group, an alkoxycarbonyl group or a group -NR ¹⁷ R ^18, Y are as defined above, R ⁹ is an alkoxy group, a haloalkoxy group, an alkenyloxy group, a halo alkenyloxy group, Alkynyloxy group, alkoxycarbonylalkoxy group, haloalkylthio group, alkenylthio group, alkynylthio group, alkoxycarbonylalkylthio group,
Alkylsulfonyl group, haloalkylsulfonyl group, optionally substituted phenylsulfonyl group, hydroxyiminoalkyl group, hydroxyiminohaloalkyl group,
Alkoxyiminoalkyl group, alkoxyiminohaloalkyl group, alkyliminoalkyl group, optionally substituted phenyliminoalkyl group, hydrazonoalkyl group, alkylhydrazonoalkyl group, optionally substituted phenylhydrazonoalkyl group, substituted Phenyl group which may be substituted, benzyl group which may be substituted, cyanoalkyl group, carbamoylalkyl group, thiocyanatoalkyl group, nitro group, hydroxyamino group, oxiranyl group which may be substituted by alkyl group or General formula

[0008]

Embedded image (Wherein, R ²⁰ represents the same meaning as described above, and R ²¹ represents a hydrogen atom, an alkyl group, an alkoxy group, a cycloalkyl group,
Alkenyl group, alkynyl group, haloalkyl group, alkoxyalkyl group, haloalkoxy group, alkenyloxy group, alkynyloxy group, alkoxycarbonylalkoxy group, alkylthio group, haloalkylthio group, alkenylthio group, alkynylthio group, alkoxycarbonylalkylthio group, Represents an alkylsulfonyl group, a haloalkylsulfonyl group, an optionally substituted phenylsulfonyl group, a hydroxyiminoalkyl group, a hydroxyiminohaloalkyl group or an alkylthioalkyl group, or R ²⁰ and R ²¹ are bonded to each other, Together with the carbon atoms present therefrom can form a 3- to 8-membered (carbon) ring. R ²² represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group,
Alkoxyalkyl group, haloalkyl group, haloalkenyl group, cyanoalkyl group, alkylthioalkyl group, alkylsulfonylalkyl group, alkylsulfinylalkyl group, alkoxycarbonylalkyl group, haloalkoxycarbonylalkyl group, carbonylalkyl group,
Carboxyalkyl, monoalkylcarbamoylalkyl, dialkylcarbamoylalkyl, acyl, alkylsulfonyl, haloalkylsulfonyl, alkoxycarbonyl, haloalkylcarbonyl, monoalkylcarbamoyl, (monoalkyl) thiocarbamoyl, dialkylcarbamoyl , (Dialkyl) thiocarbamoyl group or a benzoyl group which may be substituted. However, when R ²² is a hydrogen atom, an alkyl group or a haloalkyl group, R ²¹ excludes a hydrogen atom or an alkyl group. R ²³ is a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an alkoxyalkyl group, a haloalkenyl group, an alkoxycarbonyl group, a cycloalkyl group, a haloalkyl group, an alkoxycarbonylalkyl group, a hydroxycarbonylalkyl group, a monoalkylcarbamoylalkyl group, Dialkylcarbamoylalkyl group, acyl group, alkylsulfonyl group, haloalkylsulfonyl group, optionally substituted benzenesulfonyl group, optionally substituted benzylsulfonyl group,
Haloalkylcarbonyl group, cycloalkylcarbonyl group, alkenylcarbonyl group, alkynylcarbonyl group, alkoxycarbonyl group, monoalkylcarbamoyl group, (monoalkyl) thiocarbamoyl group, dialkylcarbamoyl group, (dialkyl) thiocarbamoyl group, even if substituted Represents a good phenyl group or a benzoyl group which may be substituted, and R ²⁴ represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an alkoxyalkyl group, a haloalkenyl group, an alkoxycarbonyl group,
Cycloalkyl group, haloalkyl group, alkoxycarbonylalkyl group, hydroxycarbonylalkyl group, monoalkylcarbamoylalkyl group, dialkylcarbamoylalkyl group, acyl group, formyl group, alkylsulfonyl group, haloalkylsulfonyl group, haloalkylcarbonyl group, alkoxycarbonyl group, Represents a monoalkylcarbamoyl group, a (monoalkyl) thiocarbamoyl group, a dialkylcarbamoyl group, a (dialkyl) thiocarbamoyl group or an optionally substituted benzoyl group, or R ²³ and R ²⁴ are bonded to each other, and Together with the present nitrogen atom can form a 3- to 8-membered (carbon) ring. R ²⁵ is a hydrogen atom, a hydroxyl group, an alkyl group, an alkoxy group, a cycloalkyl group, an alkenyl group, an alkynyl group, a haloalkyl group, an alkoxyalkyl group, a haloalkoxy group, an alkenyloxy group, an alkynyloxy group, an alkoxycarbonylalkoxy group, an alkylthio group. Group, haloalkylthio group, alkenylthio group, alkynylthio group, alkoxycarbonylalkylthio group, alkylsulfonyl group, haloalkylsulfonyl group, optionally substituted phenylsulfonyl group, hydroxyiminoalkyl group, hydroxyiminohaloalkyl group, alkylthioalkyl group or the group ^-NR 23 ^{R 24} (wherein ^{each R 23} and ^{R 24} are as defined above.) ^{represents, R 26} is a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group Cycloalkyl, alkenyl, alkynyl, haloalkyl, alkoxyalkyl, haloalkoxy, alkenyloxy, alkynyloxy, alkoxycarbonylalkoxy, alkylthio, haloalkylthio, alkenylthio, alkynylthio, carboxyl Group, an alkoxycarbonyl group, an alkenyloxycarbonyl group or an alkynyloxycarbonyl group. R ¹⁰ represents a hydrogen atom, an alkyl group, a haloalkyl group, an acyl group, a halogen atom or a nitro group, and R ¹¹ represents a hydrogen atom, a hydroxyl group, a thiol group,
Alkyl group, halogen atom, cycloalkyl group, alkenyl group, alkynyl group, haloalkyl group, cyano group, alkoxycarbonyl group, carboxyl group, alkenyloxycarbonyl group, alkynyloxycarbonyl group, haloalkoxycarbonyl group, cycloalkyloxycarbonyl group, Alkoxyalkyloxycarbonyl group, formyl group, acyl group, alkoxy group, haloalkoxy group, alkenyloxy group, haloalkenyl group, alkynyloxy group, alkoxycarbonylalkoxy group, alkylthio group, haloalkylthio group, alkenylthio group,
Alkynylthio, alkoxycarbonylalkylthio, alkylsulfonyl, haloalkylsulfonyl, optionally substituted phenylsulfonyl, hydroxyiminoalkyl, hydroxyiminohaloalkyl, alkoxyiminoalkyl, alkoxyiminohaloalkyl, alkyliminoalkyl Group, optionally substituted phenyliminoalkyl group, hydrazonoalkyl group, alkylhydrazonoalkyl group, optionally substituted phenylhydrazonoalkyl group, optionally substituted phenyl group, optionally substituted A good benzyl group, a cyanoalkyl group, a carbamoylalkyl group, a cyanoalkylthio group, a nitro group, a hydroxyamino group, an oxiranyl group optionally substituted by an alkyl group, or a general formula

[0009]

Embedded image (Wherein, R ²⁰ , R ²¹ , R ²³ , R ²⁴ , R ²⁵ , R
²⁶ and n each have the same meaning as described above, and R ^{22 ′}
Is a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, an alkoxyalkyl group, a haloalkyl group, a haloalkenyl group, a cyanoalkyl group, an alkylthioalkyl group, an alkylsulfonylalkyl group,
Alkylsulfinylalkyl group, alkoxycarbonylalkyl group, haloalkoxycarbonylalkyl group,
Carbonylalkyl group, carboxyalkyl group, monoalkylcarbamoylalkyl group, dialkylcarbamoylalkyl group, acyl group, alkylsulfonyl group, haloalkylsulfonyl group, alkoxycarbonyl group, haloalkylcarbonyl group, monoalkylcarbamoyl group,
It represents a (monoalkyl) thiocarbamoyl group, a dialkylcarbamoyl group, a (dialkyl) thiocarbamoyl group or a benzoyl group which may be substituted. ). ]
Represents 2-pyridone derivatives represented by｝.

(2) General formula [I]

[0011]

Embedded image In the formula, R ¹ is a hydrogen atom, an alkyl group, a haloalkyl group, an acetyl group, a group —N ＝ CR ¹² R ¹³ or a group —NR
¹⁷ R ¹⁸ , wherein R ¹² and R ¹³ are each independently a hydrogen atom, an alkyl group, a group —NR ¹⁷ R ¹⁸ or a phenyl group (the group is substituted with a halogen atom, a nitro group, an alkyl group, a haloalkyl group or an alkoxy group) R ¹⁷ and R ¹⁸ each independently represent a hydrogen atom, an alkyl group, a haloalkyl group, an acyl group, an alkoxycarbonyl group, a benzoyl group (the group is a halogen atom, a nitro group, an alkyl group, A haloalkyl group or an alkoxy group; a phenoxycarbonyl group (the group may be substituted with a halogen atom, a nitro group, an alkyl group, a haloalkyl group or an alkoxy group), a formyl group or an alkyl group; Represents a sulfonyl group. R ² represents a haloalkyl group; R ³ represents a hydrogen atom, an alkyl group, a carboxyl group or an alkoxycarbonyl group; R ⁴ represents a hydrogen atom, a halogen atom, an alkoxy group, a cyano group or an alkyl group;

[0012]

Embedded image Wherein, ^{R 5} represents a hydrogen atom or a halogen atom, ^{R 6}
Represents a hydrogen atom, a halogen atom, a nitro group or a cyano group, R ⁷ represents an acylalkoxy group, a dialkoxyalkoxy group, a dialkoxyalkylthio group, a hydroxycycloalkyloxy group, an alkoxycycloalkyloxy group, an acyloxycycloalkyloxy group, Alkoxycarbonyloxycycloalkyloxy group, cycloalkenyloxy group or general formula

[0013]

Embedded image Represents a group represented by the formula, Y is an oxygen atom, a sulfur atom or a group -NR ^17, Het is 3- to 6-membered heterocyclic ring (in which a halogen atom, a nitro group, an oxo group, an alkyl group, R ¹⁴ represents a hydrogen atom, an alkyl group or a cycloalkyl group, R ¹⁵ represents an alkoxyalkoxyalkyl group, an alkoxycarbonylalkyl group,
Alkenyloxycarbonylalkyl group, alkynyloxycarbonylalkyl group, cycloalkyloxycarbonylalkyl group, alkoxyalkoxycarbonylalkyl group, haloalkoxycarbonylalkyl group, haloalkenyloxycarbonylalkyl group, benzyloxycarbonylalkyl group (the benzyl group of the group is May be substituted with a halogen atom, nitro group, alkyl group, haloalkyl group or alkoxy group.), Alkylthiocarbonylalkyl group, alkylsulfinylalkoxycarbonylalkyl group, alkylsulfonylalkoxycarbonylalkyl group, monoalkylcarbamoylalkyl group, dialkyl Carbamoylalkyl group, alkylthioalkoxycarbonylalkyl group, phenoxycarbonylalkyl Group (the phenyl group of the group are a halogen atom, a nitro group, an alkyl group, optionally substituted haloalkyl group or alkoxy group.), Alkoxycarbonyl alkoxycarbonylalkyl radical, R
²⁰ represents a hydrogen atom, a halogen atom or an alkyl group.
R ⁸ represents a hydrogen atom, a halogen atom, a hydroxyl group, an alkoxy group, an alkenyloxy group, an alkynyloxy group,
Haloalkoxy group, haloalkenyloxy group or group -N
R ¹⁷ represents R ¹⁸ , Y represents the same meaning as described above, and R ⁹ represents
Is an alkoxy group, haloalkoxy group, alkenyloxy group, haloalkenyloxy group, alkynyloxy group, alkoxycarbonylalkoxy group, haloalkylthio group, alkenylthio group, alkynylthio group, alkoxycarbonylalkylthio group, alkylsulfonyl group, haloalkylsulfonyl group An optionally substituted phenylsulfonyl group, hydroxyiminoalkyl group, hydroxyiminohaloalkyl group, alkoxyiminoalkyl group, alkoxyiminohaloalkyl group, alkyliminoalkyl group, optionally substituted phenyliminoalkyl group, hydrazonoalkyl Group, alkylhydrazonoalkyl group, optionally substituted phenylhydrazonoalkyl group, optionally substituted phenyl group, optionally substituted benzyl Group, cyanoalkyl group, carbamoyl group, thiocyanatoalkyl alkyl group, a nitro group,
A hydroxyamino group, an oxiranyl group optionally substituted by an alkyl group, or a general formula

[0014]

Embedded image (Wherein, R ²⁰ represents the same meaning as described above, and R ²¹ represents a hydrogen atom, an alkyl group, an alkoxy group, a cycloalkyl group,
Alkenyl group, alkynyl group, haloalkyl group, alkoxyalkyl group, haloalkoxy group, alkenyloxy group, alkynyloxy group, alkoxycarbonylalkoxy group, alkylthio group, haloalkylthio group, alkenylthio group, alkynylthio group, alkoxycarbonylalkylthio group, Represents an alkylsulfonyl group, a haloalkylsulfonyl group, an optionally substituted phenylsulfonyl group, a hydroxyiminoalkyl group, a hydroxyiminohaloalkyl group or an alkylthioalkyl group, or R ²⁰ and R ²¹ are bonded to each other, Together with the carbon atoms present therefrom can form a 3- to 8-membered (carbon) ring. R ²² represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group,
Alkoxyalkyl group, haloalkyl group, haloalkenyl group, cyanoalkyl group, alkylthioalkyl group, alkylsulfonylalkyl group, alkylsulfinylalkyl group, alkoxycarbonylalkyl group, haloalkoxycarbonylalkyl group, carbonylalkyl group,
Carboxyalkyl, monoalkylcarbamoylalkyl, dialkylcarbamoylalkyl, acyl, alkylsulfonyl, haloalkylsulfonyl, alkoxycarbonyl, haloalkylcarbonyl, monoalkylcarbamoyl, (monoalkyl) thiocarbamoyl, dialkylcarbamoyl , (Dialkyl) thiocarbamoyl group or a benzoyl group which may be substituted. However, when R ²² is a hydrogen atom, an alkyl group or a haloalkyl group, R ²¹ excludes a hydrogen atom or an alkyl group. R ²³ is a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an alkoxyalkyl group, a haloalkenyl group, an alkoxycarbonyl group, a cycloalkyl group, a haloalkyl group, an alkoxycarbonylalkyl group, a hydroxycarbonylalkyl group, a monoalkylcarbamoylalkyl group, Dialkylcarbamoylalkyl group, acyl group, alkylsulfonyl group, haloalkylsulfonyl group, optionally substituted benzenesulfonyl group, optionally substituted benzylsulfonyl group, haloalkylcarbonyl group, cycloalkylcarbonyl group, alkenylcarbonyl group, alkynyl Carbonyl group, alkoxycarbonyl group, monoalkylcarbamoyl group, (monoalkyl) thiocarbamoyl group, dialkylcarbamoyl group, (dialkyl) thio Represents a carbamoyl group, an optionally substituted phenyl group or an optionally substituted benzoyl group, and R ²⁴ represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an alkoxyalkyl group, a haloalkenyl group, an alkoxycarbonyl group,
Cycloalkyl group, haloalkyl group, alkoxycarbonylalkyl group, hydroxycarbonylalkyl group, monoalkylcarbamoylalkyl group, dialkylcarbamoylalkyl group, acyl group, formyl group, alkylsulfonyl group, haloalkylsulfonyl group, haloalkylcarbonyl group, alkoxycarbonyl group, Represents a monoalkylcarbamoyl group, a (monoalkyl) thiocarbamoyl group, a dialkylcarbamoyl group, a (dialkyl) thiocarbamoyl group or an optionally substituted benzoyl group, or R ²³ and R ²⁴ are bonded to each other, and Together with the present nitrogen atom can form a 3- to 8-membered (carbon) ring. R ²⁵ is a hydrogen atom, a hydroxyl group, an alkyl group, an alkoxy group, a cycloalkyl group, an alkenyl group, an alkynyl group, a haloalkyl group, an alkoxyalkyl group, a haloalkoxy group, an alkenyloxy group, an alkynyloxy group, an alkoxycarbonylalkoxy group, an alkylthio group. Group, haloalkylthio group, alkenylthio group, alkynylthio group, alkoxycarbonylalkylthio group, alkylsulfonyl group, haloalkylsulfonyl group, optionally substituted phenylsulfonyl group, hydroxyiminoalkyl group, hydroxyiminohaloalkyl group, alkylthioalkyl group or the group ^-NR 23 ^{R 24} (wherein ^{each R 23} and ^{R 24} are as defined above.) ^{represents, R 26} is a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group Cycloalkyl, alkenyl, alkynyl, haloalkyl, alkoxyalkyl, haloalkoxy, alkenyloxy, alkynyloxy, alkoxycarbonylalkoxy, alkylthio, haloalkylthio, alkenylthio, alkynylthio, carboxyl Group, an alkoxycarbonyl group, an alkenyloxycarbonyl group or an alkynyloxycarbonyl group. R ¹⁰ represents a hydrogen atom, an alkyl group, a haloalkyl group, an acyl group, a halogen atom or a nitro group, and R ¹¹ represents a hydrogen atom, a hydroxyl group, a thiol group,
Alkyl group, halogen atom, cycloalkyl group, alkenyl group, alkynyl group, haloalkyl group, cyano group, alkoxycarbonyl group, carboxyl group, alkenyloxycarbonyl group, alkynyloxycarbonyl group, haloalkoxycarbonyl group, cycloalkyloxycarbonyl group, Alkoxyalkyloxycarbonyl group, formyl group, acyl group, alkoxy group, haloalkoxy group, alkenyloxy group, haloalkenyl group, alkynyloxy group, alkoxycarbonylalkoxy group, alkylthio group, haloalkylthio group, alkenylthio group,
Alkynylthio, alkoxycarbonylalkylthio, alkylsulfonyl, haloalkylsulfonyl, optionally substituted phenylsulfonyl, hydroxyiminoalkyl, hydroxyiminohaloalkyl, alkoxyiminoalkyl, alkoxyiminohaloalkyl, alkyliminoalkyl Group, optionally substituted phenyliminoalkyl group, hydrazonoalkyl group, alkylhydrazonoalkyl group, optionally substituted phenylhydrazonoalkyl group, optionally substituted phenyl group, optionally substituted A good benzyl group, a cyanoalkyl group, a carbamoylalkyl group, a cyanoalkylthio group, a nitro group, a hydroxyamino group, an oxiranyl group optionally substituted by an alkyl group, or a general formula

[0015]

Embedded image (Wherein, R ²⁰ , R ²¹ , R ²³ , R ²⁴ , R ²⁵ , R
²⁶ and n each have the same meaning as described above, and R ^{22 ′}
Is a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, an alkoxyalkyl group, a haloalkyl group, a haloalkenyl group, a cyanoalkyl group, an alkylthioalkyl group, an alkylsulfonylalkyl group,
Alkylsulfinylalkyl group, alkoxycarbonylalkyl group, haloalkoxycarbonylalkyl group,
Carbonylalkyl group, carboxyalkyl group, monoalkylcarbamoylalkyl group, dialkylcarbamoylalkyl group, acyl group, alkylsulfonyl group, haloalkylsulfonyl group, alkoxycarbonyl group, haloalkylcarbonyl group, monoalkylcarbamoyl group,
It represents a (monoalkyl) thiocarbamoyl group, a dialkylcarbamoyl group, a (dialkyl) thiocarbamoyl group or a benzoyl group which may be substituted. ). ]
Represents 2-pyridone derivatives represented by｝. (3) General formula [I]

[0016]

Embedded image In the formula, R ¹ is a hydrogen atom, an alkyl group, a haloalkyl group, an acetyl group, a group —N ＝ CR ¹² R ¹³ or a group —NR
¹⁷ R ¹⁸ , wherein R ¹² and R ¹³ are each independently a hydrogen atom, an alkyl group, a group —NR ¹⁷ R ¹⁸ or a phenyl group (the group is substituted with a halogen atom, a nitro group, an alkyl group, a haloalkyl group or an alkoxy group) R ¹⁷ and R ¹⁸ each independently represent a hydrogen atom, an alkyl group, a haloalkyl group, an acyl group, an alkoxycarbonyl group, a benzoyl group (the group is a halogen atom, a nitro group, an alkyl group, A haloalkyl group or an alkoxy group; a phenoxycarbonyl group (the group may be substituted with a halogen atom, a nitro group, an alkyl group, a haloalkyl group or an alkoxy group), a formyl group or an alkyl group; Represents a sulfonyl group. R ² represents a haloalkyl group; R ³ represents a hydrogen atom, an alkyl group, a carboxyl group or an alkoxycarbonyl group; R ⁴ represents a hydrogen atom, a halogen atom, an alkoxy group, a cyano group or an alkyl group;

[0017]

Embedded image Wherein, ^{R 5} represents a hydrogen atom or a halogen atom, ^{R 6}
Represents a hydrogen atom, a halogen atom, a nitro group or a cyano group, R ⁷ represents an acylamino group, a dialkoxycarbonylalkylthio group, a dialkoxycarbonylalkoxy group,
Dialkoxyphosphonylalkyl group, epoxycycloalkyl group, cycloalkyl group (alkenyloxy group, alkylsulfonyloxy group or alkyl-substituted) or a general formula

[0018]

Embedded image (Wherein, R ²⁰ represents a hydrogen atom, a halogen atom or an alkyl group, and R ²⁵ represents a hydrogen atom, a hydroxyl group, an alkyl group, an alkoxy group, a cycloalkyl group, an alkenyl group, an alkynyl group, a haloalkyl group, an alkoxyalkyl group, Haloalkoxy group, alkenyloxy group, alkynyloxy group, alkoxycarbonylalkoxy group, alkylthio group, haloalkylthio group, alkenylthio group, alkynylthio group, alkoxycarbonylalkylthio group, alkylsulfonyl group, haloalkylsulfonyl group, even if substituted phenyl sulfonyl group, hydroxyimino group, hydroxyimino haloalkyl group, an alkylthioalkyl group or a group -NR ²³ R
²⁴ (wherein, R ²³ represents R ²⁴ represents a hydrogen atom, an alkyl group,
Alkenyl group, alkynyl group, alkoxyalkyl group,
Haloalkenyl group, alkoxycarbonyl group, cycloalkyl group, haloalkyl group, alkoxycarbonylalkyl group, hydroxycarbonylalkyl group, monoalkylcarbamoylalkyl group, dialkylcarbamoylalkyl group, acyl group, formyl group, alkylsulfonyl group, haloalkylsulfonyl group, Optionally substituted benzenesulfonyl, optionally substituted benzylsulfonyl, haloalkylcarbonyl, cycloalkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, alkoxycarbonyl, monoalkylcarbamoyl, (monoalkyl) A thiocarbamoyl group, a dialkylcarbamoyl group, a (dialkyl) thiocarbamoyl group, an optionally substituted phenyl group, or an optionally substituted Represents a benzoyl group, R ²⁴ is a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an alkoxyalkyl group, a haloalkenyl group, an alkoxycarbonyl group, a cycloalkyl group, a haloalkyl group, an alkoxycarbonylalkyl group, hydroxycarbonyl group, mono Alkylcarbamoylalkyl group, dialkylcarbamoylalkyl group, acyl group, formyl group,
Represents an alkylsulfonyl group, a haloalkylsulfonyl group, a haloalkylcarbonyl group, an alkoxycarbonyl group, a monoalkylcarbamoyl group, a (monoalkyl) thiocarbamoyl group, a dialkylcarbamoyl group, a (dialkyl) thiocarbamoyl group or a benzoyl group which may be substituted. , R ²⁶ represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a cycloalkyl group, an alkenyl group, an alkynyl group, a haloalkyl group, an alkoxyalkyl group, a haloalkoxy group, an alkenyloxy group, an alkynyloxy group, an alkoxycarbonylalkoxy group,
Represents an alkylthio group, a haloalkylthio group, an alkenylthio group, an alkynylthio group, a carboxyl group, an alkoxycarbonyl group, an alkenyloxycarbonyl group or an alkynyloxycarbonyl group. ). R ⁸ represents a hydrogen atom, a halogen atom, a hydroxyl group, an alkoxy group,
Represents an alkenyloxy group, an alkynyloxy group, a haloalkoxy group, a haloalkenyloxy group, an alkoxycarbonylalkyl group, or a group -NR ¹⁷ R ¹⁸ .

(4) General formula [I ']

[0020]

Embedded image In the formula, R ^{1 ′} represents a hydrogen atom, an alkyl group or a haloalkyl group; R ^{3 ′} represents a hydrogen atom or an alkyl atom;

[0021]

Embedded image [Wherein, R ^{5 ′} represents a hydrogen atom or a halogen atom;
^{6 ′} represents a halogen atom or a cyano group, R ^{7 ′} represents a hydrogen atom, a halogen atom, a nitro group, an alkoxy group, an alkenyloxy group, a phenyloxy group, an amino group, a hydroxy group, an alkoxyalkylthio group, an alkynyloxy group, Alkoxy group, alkoxyalkoxy group, acylalkoxy group, alkoxycarbonylalkoxy group, alkoxycarbonylhaloalkoxy group, cycloalkoxy group, alkylaminocarbonylalkoxy group, cycloalkylaminocarbonylalkoxy group, alkenylaminocarbonylalkoxy group, alkynylaminocarbonylalkoxy group An alkoxycarbonylalkoxycarbonylalkoxy group, an alkoxyalkoxycarbonylalkoxy group, an alkylthioalkoxycarbonylalkoxy group, Alkoxycarbonyl alkoxycarbonylalkyl thio group, alkoxycarbonyl alkoxycarbonylalkyl thio group, an alkyl thio alkoxycarbonylalkyl thio group, an alkylamino group, a dialkylamino group, alkynyl group, a cycloalkyl group, an alkylsulfonylamino group, N- alkyl -N-
Alkynylamino group, N-alkyl-N-alkoxyalkylamino group, alkoxycarbonylalkoxycarbonyl group, alkenyloxycarbonylalkoxycarbonyl group, haloalkenyloxycarbonylalkoxycarbonyl group, cycloalkylalkylthio group, alkynyloxycarbonylalkoxycarbonyl group, alkoxyalkoxy Represents a carbonylalkoxycarbonyl group or a carboxylalkoxy group, R ^{8 ′} is a hydrogen atom,
Represents a halogen atom, a hydroxyl group, an amino group or an alkoxy group. Y represents the same meaning as described above, and R ^{9 ′} represents an alkyl group, a haloalkyl group, a hydroxyalkyl group, an alkoxyalkyl group, a haloalkoxyalkyl group, an alkylthioalkyl group, an alkylsulfinylalkyl group,
It represents an alkylsulfonylalkyl group, a carboxyl group, an alkoxycarbonyl group, a haloalkoxycarbonyl group, a cycloalkyloxycarbonyl group or an alkynyloxycarbonyl group, and R ^{10 ′} represents a hydrogen atom or an alkyl group. ]. 2-pyridone derivatives represented by｝.

(5) and a herbicide containing the same as an active ingredient.

In the present specification, the halogen atom means a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

The alkyl group means a linear or branched alkyl group having 1 to 6 carbon atoms, such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group,
Examples thereof include an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a neopentyl group, an n-hexyl group, an isohexyl group, and a 3,3-dimethylbutyl group.

The haloalkyl group is an alkyl group having 1 to 6 carbon atoms substituted by a halogen atom, and examples thereof include a difluoromethyl group, a trifluoromethyl group and a pentafluoroethyl group.

The alkenyl group is a linear or branched alkenyl group having 2 to 6 carbon atoms, and examples thereof include a vinyl group, a propenyl group, an isopropenyl group, a butenyl group, a pentenyl group and a hexenyl group. .

The haloalkenyl group is a straight or branched alkenyl group having 3 to 6 carbon atoms, which is substituted by a halogen atom, such as 2-chloro-2-propenyl group,
Examples thereof include a 3-chloro-2-propenyl group.

The alkynyl group means a linear or branched alkynyl group having 3 to 6 carbon atoms, for example, a propynyl group,
Examples thereof include a butynyl group, a pentynyl group, a hexynyl group, a 3,3-dimethyl-1-butynyl group, a 4-methyl-1-pentynyl group, and a 3-methyl-1-pentynyl group.

The cycloalkyl group is a cycloalkyl group having 3 to 8 carbon atoms, such as a cyclopropyl group and a cyclohexyl group.

The acyl group is an alkylcarbonyl group, an alkenylcarbonyl group, an alkynylcarbonyl group, a haloalkylcarbonyl group, a haloalkenylcarbonyl group, a cycloalkylcarbonyl group or a formyl group.

Examples of the 3- to 6-membered heterocyclic group include a pyrimidinyl group, a pyridyl group, a thienyl group, a thiazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, an oxolanyl group, a dioxolanyl group, and an oxiranyl group.

[0032]

Next, specific examples of the compound of the present invention are shown in Tables 1 to 56. However, the compounds of the present invention are not limited to these compounds. The compound numbers will be referred to in the following description.

Also, Compound No. 2-15 and Compound No. 2-16, and Compound No. 3-15 and Compound No. 3-
16 have diastereomeric relationships, and the thin-layer chromatography on silica gel (normal phase) shows that the former has a lower polarity and the latter has a higher polarity. Unless otherwise indicated represents a mixture of diastereomers. Unless otherwise specified for the double bond, it indicates an EZ mixture.

[0034]

[Table 1]

[0035]

[Table 2]

[0036]

[Table 3]

[0037]

[Table 4]

[0038]

[Table 5]

[0039]

[Table 6]

[0040]

[Table 7]

[0041]

[Table 8]

[0042]

[Table 9]

[0043]

[Table 10]

[0044]

[Table 11]

[0045]

[Table 12]

[0046]

[Table 13]

[0047]

[Table 14]

[0048]

[Table 15]

[0049]

[Table 16]

[0050]

[Table 17]

[0051]

[Table 18]

[0052]

[Table 19]

[0053]

[Table 20]

[0054]

[Table 21]

[0055]

[Table 22]

[0056]

[Table 23]

[0057]

[Table 24]

[0058]

[Table 25]

[0059]

[Table 26]

[0060]

[Table 27]

[0061]

[Table 28]

[0062]

[Table 29]

[0063]

[Table 30]

[0064]

[Table 31]

[0065]

[Table 32]

[0066]

[Table 33]

[0067]

[Table 34]

[0068]

[Table 35]

[0069]

[Table 36]

[0070]

[Table 37]

[0071]

[Table 38]

[0072]

[Table 39]

[0073]

[Table 40]

[0074]

[Table 41]

[0075]

[Table 42]

[0076]

[Table 43]

[0077]

[Table 44]

[0078]

[Table 45]

[0079]

[Table 46]

[0080]

[Table 47]

[0081]

[Table 48]

[0082]

[Table 49]

[0083]

[Table 50]

[0084]

[Table 51]

[0085]

[Table 52]

[0086]

[Table 53]

[0087]

[Table 54]

[0088]

[Table 55]

[0089]

[Table 56]

The compound of the present invention can be produced, for example, according to the following production method. However, the production method is not limited to these methods. <Production Method 1> First, the starting materials will be described.

[0091]

Embedded image (Wherein Q ″ represents Q or Q ′, X represents a halogen atom, and Q, Q ′, R ⁵ , R ⁶ , R ⁷ and R ⁸ each have the same meaning as described above.) The compound represented by the formula [II-3] can be produced by halogenating the compound represented by the formula [II-1], for example, phosphorus tribromide, thionyl bromide, chloride, etc. It is possible to use thionyl, hydrogen chloride, hydrogen bromide, etc. As the solvent, use ethers such as diethyl ether, tetrahydrofuran (THF) or dioxane, or hydrocarbons such as n-hexane, benzene or toluene. The above reaction is optionally carried out under a stream of nitrogen at -10.
The reaction is carried out at a temperature in the range of from 0 ° C to the boiling point of the solvent, and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

By reacting the compound represented by the general formula [II-2] with methoxymethyl chloride in the presence of a Lewis acid, X of the compound represented by the general formula [II-3] is obtained. Can produce those of chlorine atom. As the Lewis acid, for example, titanium tetrachloride or aluminum chloride can be used. As the solvent, for example, halogenated hydrocarbons such as methylene chloride, chloroform or carbon tetrachloride or ethers such as diethyl ether, THF or dioxane can be used. The above reaction is optionally carried out under a stream of nitrogen at -10.
The reaction is carried out at a temperature in the range of from 0 ° C to the boiling point of the solvent, and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

Next, the compound represented by the general formula [II-4] can be produced by reacting the obtained compound represented by the general formula [II-3] with a cyanating agent. . As the cyanating agent, for example, sodium cyanide or potassium cyanide can be used. Examples of the solvent include ethers such as diethyl ether, THF or dioxane, hydrocarbons such as n-hexane, benzene or toluene, aliphatic ketones such as acetone or methyl ethyl ketone, alcohols such as methanol or ethanol, and acetonitrile, N, N -Dimethylformamide (DMF), N, N-dimethylacetamide (DM
AC) or N, N-dimethylsulfoxide (DMSO)
And other aprotic polar solvents. The above reaction is optionally carried out under a stream of nitrogen at -10.
The reaction is carried out at a temperature in the range of from 0 ° C to the boiling point of the solvent, and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

The compound of the present invention can be produced as follows using the compound represented by the formula [II-4] as a starting material.

[0095]

Embedded image (In the formula, Q ″, R ¹ , R ² , R ³ , R ⁴ and X each have the same meaning as described above, and Et represents an ethyl group.) A compound represented by the general formula [II-4] Formula [II-
The compound of the present invention represented by the general formula [II-10] and the compound of the general formula [II-11] by reacting the compound represented by the formula [7] in the presence of a base and then treating with an acid. Mixtures with the compounds represented can be prepared. As a base, for example, triethylamine, 1,8-diazabicyclo-
Organic amines such as [5.4.0] -7-undecene (DBU), pyridine, picoline or quinoline or sodium methoxide, potassium tert-butoxide;
Sodium hydroxide, potassium hydroxide, sodium carbonate,
Inorganic bases such as potassium carbonate, sodium acetate, potassium acetate, sodium hydrogen carbonate and potassium hydrogen carbonate can be used. As a solvent, for example, ethers such as diethyl ether, THF or dioxane, hydrocarbons such as n-hexane, benzene or toluene, aliphatic ketones such as acetone or methyl ethyl ketone or aprotic polar such as acetonitrile, DMF, DMAC or DMSO A solvent or the like can be used. As the acid, for example, hydrochloric acid or sulfuric acid can be used. The above reaction is carried out in the range of -10 ° C to the boiling point of the solvent,
Usually, it is completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.
The compound of the present invention represented by the general formula [II-10] includes a keto-enol tautomer.

Next, the obtained compound of the present invention represented by the general formula [II-10] and the compound represented by the general formula [II-13] or 2,4-dinitrophenoxyamine are reacted in the presence of a base. In some cases, the compound of the present invention represented by the general formula [II] can be produced by reacting using a phase transfer catalyst. As a base, for example, organic amines such as triethylamine, DBU, pyridine, picoline or quinoline or sodium, sodium hydride, sodium methoxide, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium acetate, Potassium acetate,
An inorganic base such as sodium hydrogencarbonate or potassium hydrogencarbonate can be used. As the phase transfer catalyst, for example, tetra-n-butylammonium bromide or benzyltriethylammonium chloride can be used. As the solvent, for example, halogenated hydrocarbons such as methylene chloride, chloroform or carbon tetrachloride, ethers such as diethyl ether, THF or dioxane, hydrocarbons such as n-hexane, benzene or toluene, aliphatics such as acetone or methyl ethyl ketone Ketones, carboxylic acids such as acetic acid or acetonitrile, DMF, DM
An aprotic polar solvent such as AC or DMSO can be used. The above reaction is carried out in the range of -10 ° C to the boiling point of the solvent, and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

As another method, the compound represented by the general formula [II-11]
The compound of the present invention represented by the general formula [II] can also be produced by reacting the compound represented by the general formula [II-12] with the compound represented by the general formula [II-12]. As the solvent, for example, halogenated hydrocarbons such as methylene chloride, chloroform or carbon tetrachloride, ethers such as diethyl ether, THF or dioxane, hydrocarbons such as n-hexane, benzene or toluene, aliphatics such as acetone or methyl ethyl ketone Ketones, carboxylic acids such as acetic acid, alcohols such as methanol or ethanol, or aprotic polar solvents such as acetonitrile, DMF, DMAC or DMSO can be used. The above reaction is carried out under anhydrous conditions in the range of -10 ° C to the boiling point of the solvent, and is usually completed in 1 to 24 hours. In some cases, the intermediate amide derivative is isolated and then closed in the presence of an acid catalyst such as paratoluenesulfonic acid. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

Further, the compound of the present invention represented by the general formula [II-10] may be, alternatively, a compound represented by the general formula [II-8] and a compound represented by the general formula [II-9]. Can also be produced. Examples of the solvent include acids such as acetic acid and polyphosphoric acid, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, ethers such as diethyl ether, THF and dioxane, n-
Hydrocarbons such as hexane, benzene or toluene, or aprotic polar solvents such as acetonitrile, DMF, DMAC or DMSO can be used. The above reaction is carried out in the range of room temperature to the boiling point of the solvent and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

The compound represented by the general formula [II-8] can be produced by reacting the compound represented by the general formula [II-4] with ethyl formate in the presence of a base. . As a base, for example, triethylamine, DB
Organic amines such as U, pyridine, picoline or quinoline or sodium, sodium hydride, sodium methoxide, sodium ethoxide, potassium tert-
Inorganic bases such as butoxide, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium acetate, potassium acetate, sodium hydrogen carbonate and potassium hydrogen carbonate can be used. As the solvent, for example, ethers such as diethyl ether, THF or dioxane, hydrocarbons such as n-hexane, benzene or toluene, aliphatic ketones such as acetone or methyl ethyl ketone, alcohols such as methanol or ethanol or acetonitrile, DMF, DMAC Alternatively, an aprotic polar solvent such as DMSO can be used. The above reaction is carried out in the range of room temperature to the boiling point of the solvent.
Ends in ~ 24 hours. If necessary, after isolating the salt, the salt is taken out with acidification with acetic acid or the like. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

As another method, the compound represented by the general formula [II-11] is prepared by converting the compound represented by the general formula [II-6] and the compound represented by the general formula [II-7] to a base. And then treating with an acid. As a base, for example, organic amines such as lithium diisopropylamide (LDA), triethylamine, DBU, pyridine, picoline or quinoline, or sodium methoxide, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium acetate And inorganic bases such as potassium acetate, sodium hydrogen carbonate and potassium hydrogen carbonate. Examples of the solvent include ethers such as diethyl ether, THF, and dioxane;
Hydrocarbons such as hexane, benzene or toluene, or aprotic polar solvents such as acetonitrile, DMF, DMAC or DMSO can be used. As the acid, for example, hydrochloric acid or sulfuric acid can be used.
The above reaction is carried out in a temperature range from -70 ° C to the boiling point of the solvent, and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

The compound represented by the general formula [II-6] can be produced by reacting the compound represented by the general formula [II-5] with ethanol in the presence of an acid. Ethanol is used as a solvent. As the acid, for example, hydrochloric acid or sulfuric acid can be used. The above reaction is carried out in the range of room temperature to the boiling point of the solvent and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography. <Production method 2>

[0102]

Embedded image [Wherein, X, R ⁵ and R ⁶ each have the same meaning as described above, R ¹⁶ represents an alkyl group, and R ^{16 ′} represents an acylalkyl group, a dialkoxyalkyl group, an alkoxycycloalkyl group, a cycloalkenyl group or General formula

[0103]

Embedded image (Wherein, R ¹⁴ , R ¹⁵ , R ²⁰ , Y and Het each have the same meaning as described above), and P is a general formula.

[0104]

Embedded image (Wherein, R ¹ , R ² , R ³ and R ⁴ each have the same meaning as described above). The compound represented by the general formula [III-2] can be reacted with a Lewis acid to produce a compound represented by the general formula [III-2]. As the Lewis acid, for example, boron tribromide or aluminum chloride can be used.
As a solvent, for example, methylene chloride, chloroform or halogenated hydrocarbons such as carbon tetrachloride, diethyl ether,
Ethers such as THF or dioxane, n-hexane,
Hydrocarbons such as benzene or toluene can be used. The above reaction is carried out in the range of -10 ° C to the boiling point of the solvent, and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method.
Further, if necessary, purification is performed by recrystallization or column chromatography.

Next, the compound represented by the general formula [III-2] and the compound represented by the general formula [III-3] or the compound represented by the general formula [III-4] are reacted in the presence of a base. Or by reacting the compound represented by the general formula [III-5] with a compound represented by the general formula [III-5] in the presence of diethyl azodicarboxylate and triphenylphosphine. Compounds can be prepared. As a base, for example, triethylamine, DB
Organic amines such as U, pyridine, picoline or quinoline, or sodium methoxide, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium acetate, potassium acetate, sodium hydrogen carbonate or potassium hydrogen carbonate, etc. And the like. As the solvent, for example, halogenated hydrocarbons such as methylene chloride, chloroform or carbon tetrachloride, ethers such as diethyl ether, THF or dioxane, hydrocarbons such as n-hexane, benzene or toluene, aliphatics such as acetone or methyl ethyl ketone Carboxylic acids such as ketones and acetic acid, or aprotic polar solvents such as acetonitrile, DMF, DMAC and DMSO can be used. The above reaction is carried out at a temperature ranging from room temperature to the boiling point of the solvent.
Ends in ~ 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography. <Production method 3>

[0106]

Embedded image (Wherein, P, R ⁵ and R ⁶ each have the same meaning as described above, and R ²⁷ represents a C ₁ -C ₅ alkyl group or a hydrogen atom.) The present invention represented by the general formula [IV-1] By subjecting the compound to a ring-closing reaction in the presence of cesium fluoride, a compound of the general formula [I
V] of the present invention.
As a solvent, for example, N, N-diethylaniline or N, N
N, N-dialkylanilines such as -dimethylaniline can be used. The above reaction is carried out in the range of room temperature to the boiling point of the solvent and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography. <Production method 4>

[0107]

Embedded image (Wherein, P, R ⁵ , R ⁶ , R ^{16 ′} and X each have the same meaning as described above.) By reacting the compound represented by the general formula [V-1] with a chlorosulfonating agent, The compound represented by the general formula [V-2] can be produced. As the chlorosulfonating agent, for example, chlorosulfonic acid, or a mixed solution of sulfuric anhydride or sulfuric acid and carbon tetrachloride can be used. The above reaction is carried out in the range of -10 ° C to the boiling point of the solvent, and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

Next, the compound represented by the general formula [V-3] can be produced by reducing the compound represented by the general formula [V-2]. As the reducing agent, for example, a mixture of red phosphorus and iodine, zinc, or the like can be used. For example, acetic acid or the like can be used as the solvent.
The above reaction is carried out in the range of room temperature to the boiling point of the solvent,
Usually, it is completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

Next, the compound represented by the general formula [V-4] is alkali-hydrolyzed to give the compound represented by the general formula [V-4]
Can be produced. As the alkali, for example, sodium hydroxide or potassium hydroxide can be used. As a solvent, for example, methanol, ethanol,
Water or a mixture thereof can be used. The above reaction is carried out in the range of room temperature to the boiling point of the solvent and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

By the same method as in Production method 2, the compound represented by the general formula [V
-4] and a compound represented by the general formula [III-3] or a compound represented by the general formula [III-4] in the presence of a base to obtain a compound represented by the general formula [ V] of the present invention. As a base, for example, sodium, sodium hydride,
Sodium hydroxide, potassium hydroxide, sodium carbonate,
An inorganic base such as potassium carbonate, sodium hydrogencarbonate or potassium hydrogencarbonate, or an organic amine such as triethylamine, DBU, pyridine, picoline or quinoline can be used. As the solvent, for example, halogenated hydrocarbons such as methylene chloride, chloroform or carbon tetrachloride, ethers such as diethyl ether, THF or dioxane, hydrocarbons such as n-hexane, benzene or toluene, aliphatics such as acetone or methyl ethyl ketone Ketones or aprotic polar solvents such as acetonitrile, DMF, DMAC or DMSO can be used. The above reaction is carried out in the range of -10 ° C to the boiling point of the solvent, and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method.
Further, if necessary, purification is performed by recrystallization or column chromatography. <Production method 5>

[0111]

Embedded image (In the formula, P, R ⁵ , R ⁶ and R ²⁷ each have the same meaning as described above.) The compound represented by the general formula [VI-1] is generally subjected to a ring-closing reaction in the presence of cesium fluoride. The compound represented by the formula [VI] can be produced. As the solvent, for example, N, N-dialkylanilines such as N, N-diethylaniline or N, N-dimethylaniline can be used. The above reaction is carried out in the range of room temperature to the boiling point of the solvent and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography. <Production method 6>

[0112]

Embedded image (In the formula, Q, X, R ¹² , R ¹³ , R ¹⁷ and R ¹⁸ each have the same meaning as described above.) The compound of the present invention represented by the general formula [VII-1] is represented by the general formula [VII-2] Is optionally reacted with a Lewis acid to give a compound of the general formula [VI
The compound of the present invention represented by I] can be produced.
Paratoluenesulfonic acid or titanium tetrachloride can be used as the Lewis acid. As the solvent, for example, halogenated hydrocarbons such as methylene chloride, chloroform or carbon tetrachloride, ethers such as diethyl ether, THF or dioxane, hydrocarbons such as n-hexane, benzene or toluene, or acetonitrile, DMF, DMAC
And other aprotic polar solvents. The above reaction is carried out in the range of -10 ° C to the boiling point of the solvent, and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

Next, the compound of the present invention represented by the general formula [VII-1] and the compound represented by the general formula [VIII-1] are optionally reacted in the presence of a base to give a general compound The compound of the present invention represented by the formula [VIII "] or the compound of the present invention represented by the general formula [VIII] can be produced. As a base, for example, sodium, sodium hydride, sodium hydroxide, potassium hydroxide, carbonate Inorganic bases such as sodium or potassium carbonate or organic amines such as triethylamine, DBU, pyridine, picoline or quinoline, etc. As solvents, halogenated hydrocarbons such as methylene chloride, chloroform or carbon tetrachloride, Diethyl ether, TH
Ethers such as F or dioxane, hydrocarbons such as n-hexane, benzene or toluene, aliphatic ketones such as acetone or methyl ethyl ketone, or aprotic polar solvents such as acetonitrile, DMF and DMAC can be used. . The above reaction is carried out in the range of -10 ° C to the boiling point of the solvent, and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

Next, the compound of the present invention represented by the general formula [VIII] and the compound represented by the general formula [VIII-2] are optionally reacted in the presence of a base to give a compound of the general formula [VIII] VIII ′] of the present invention. As a base, for example, sodium, sodium hydride, sodium hydroxide, potassium hydroxide,
Inorganic bases such as sodium carbonate or potassium carbonate or organic amines such as triethylamine, DBU, pyridine, picoline or quinoline can be used.
As a solvent, for example, methylene chloride, chloroform or halogenated hydrocarbons such as carbon tetrachloride, diethyl ether,
Ethers such as THF or dioxane, n-hexane,
Hydrocarbons such as benzene or toluene, aliphatic ketones such as acetone or methyl ethyl ketone, or aprotic polar solvents such as acetonitrile, DMF, and DMAC can be used. The above reaction is carried out in the range of -10 ° C to the boiling point of the solvent, and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography. <Production method 7>

[0115]

Embedded image (Wherein, P, X, R ⁵ , R ⁶ , R ²² and R ²⁷ each have the same meaning as described above, and R ^{22 ″} is an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, an alkoxyalkyl group, a haloalkyl Group, haloalkenyl group,
Represents an alkylthioalkyl group, an alkylsulfonylalkyl group, an alkylsulfinylalkyl group, an alkoxycarbonylalkyl group, a haloalkoxycarbonylalkyl group, a carbonylalkyl group, a hydroxycarbonylalkyl group, a monoalkylcarbamoylalkyl group or a dialkylcarbamoylalkyl group. However, [X ']
In formula (IX), an alkylthioalkyl group or an alkylsulfinylalkyl group is excluded.) The compound represented by the general formula [IX-1] is brominated to obtain a compound represented by the general formula [IX-2] A brominated agent such as N-bromosuccinimide (NBS) can be used.
For example, 2,2'-azobisisobutyronitrile can be used as a catalyst. As the solvent, for example, halogenated hydrocarbons such as carbon tetrachloride and the like can be used. The above reaction is optionally carried out under a stream of nitrogen at -10.
The reaction is carried out at a temperature in the range of from 0 ° C to the boiling point of the solvent, and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

Next, the compound represented by the general formula [IX-2] is reacted with the compound represented by the general formula [IX-3] in the presence or absence of a base to obtain a compound represented by the general formula [IX-2]. I
X] can be produced.
As the base, for example, an inorganic base such as sodium, sodium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate or potassium carbonate can be used.
As a solvent, for example, ethers such as diethyl ether, THF or dioxane, hydrocarbons such as n-hexane, benzene or toluene, aliphatic ketones such as acetone or methyl ethyl ketone, acetonitrile, DMF, DMA
An aprotic polar solvent such as C or DMSO or an excess of the compound represented by the general formula [IX-3] can be used. The above reaction may be carried out in a range of from −10 ° C. to the boiling point of the solvent under a nitrogen stream in some cases.
Ends in 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

Next, a compound represented by the general formula [IX] is reacted with a compound represented by the general formula [X-1] in the presence of a base to give a compound represented by the general formula [X]. Can be produced. As the base, for example, an inorganic base such as sodium, sodium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate or potassium carbonate can be used. As a solvent, for example, ethers such as diethyl ether, THF or dioxane, hydrocarbons such as n-hexane, benzene or toluene, aliphatic ketones such as acetone or methyl ethyl ketone, or acetonitrile, DMF, DMAC or DM
An aprotic polar solvent such as SO can be used. The above reaction is carried out in the range of -10 ° C to the boiling point of the solvent, and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Also,
Purify by recrystallization or column chromatography as needed.

Next, the compound of the present invention represented by the general formula [X '] or [X "] can be produced by reacting the compound of the present invention represented by the general formula [X] with an oxidizing agent. As the oxidizing agent, for example, metachloroperbenzoic acid or potassium monosulfate (trade name: Oxone) can be used.
Ethers such as THF or dioxane, n-hexane,
Use hydrocarbons such as benzene or toluene, aliphatic ketones such as acetone or methyl ethyl ketone, or aprotic polar solvents such as acetonitrile, DMF, DMAC or DMSO, and halogenated solvents such as methylene chloride, chloroform and carbon tetrachloride. Can be. The above reaction is carried out in the range of -10 ° C to the boiling point of the solvent, and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

Next, the compound of the present invention represented by the general formula [IX ′] can be produced by reacting the compound represented by the general formula [IX-2] with silver nitrate or sodium acetate. As the solvent, for example, water alone or water and ethers such as diethyl ether, THF or dioxane, hydrocarbons such as n-hexane, benzene or toluene, aliphatic ketones such as acetone or methyl ethyl ketone or acetonitrile, DMF, DMAC or DM
A mixed solution of aprotic polar solvent such as SO or the like and water can be used. The above reaction is carried out in the range of -10 ° C to the boiling point of the solvent, and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

Next, the compound of the formula [IX '] is reacted with the compound of the formula [IX'] and the compound of the formula [IX-4] in the presence of a base. The compound of the present invention represented by the following formula: can be used as a base, for example, an inorganic base such as sodium, sodium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate or potassium carbonate can be used. For example, ethers such as diethyl ether, THF or dioxane, hydrocarbons such as n-hexane, benzene or toluene, aliphatic ketones such as acetone or methyl ethyl ketone or acetonitrile, DMF, DMA
An aprotic polar solvent such as C or DMSO can be used. The above reaction is carried out in the range of -10 ° C to the boiling point of the solvent, and is usually completed in 1 to 24 hours.
The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography. <Production method 8>

[0121]

Embedded image (Wherein, P, R ⁵ and R ⁶ have the same meanings as described above.) The compound represented by the general formula [XI-1] is brominated to be represented by the general formula [XI-2]. Can be produced. For example, NBS can be used as a brominating agent. For example, 2,2'-azobisisobutyronitrile can be used as a catalyst. As the solvent, for example, halogenated hydrocarbons such as carbon tetrachloride and the like can be used. The above reaction is optionally carried out in a range of -10 ° C to the boiling point of the solvent under a nitrogen stream, and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

The compound of the present invention represented by the general formula [XI] can be produced by treating the compound represented by the general formula [XI-2] with an acid. Sulfuric acid and hydrochloric acid can be used as the acid. The above reaction is optionally carried out in a range of -10 ° C to the boiling point of the solvent under a nitrogen stream, and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography. <Production method 9>

[0123]

Embedded image (Wherein, P, X, Y, R ⁵ , R ⁶ , R ²³ and R ²⁴ represent the same meaning as described above, and R ²⁸ represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, an alkoxy group, Alkyl group, haloalkyl group, haloalkenyl group, alkylthioalkyl group, alkylsulfonylalkyl group, alkylsulfinylalkyl group, alkoxycarbonylalkyl group, haloalkoxycarbonylalkyl group, carbonylalkyl group, hydroxycarbonylalkyl group, monoalkylcarbamoylalkyl group or Next, a compound represented by the general formula [XII-2] can be produced by reducing the compound represented by the general formula [XII-1]. As the reducing agent, for example, iron or tin / hydrochloric acid can be used. Examples of the solvent include carboxylic acids such as acetic acid, hydrocarbons such as benzene and toluene, alcohols such as methanol and ethanol, and water. The above reaction is carried out in the range of room temperature to the boiling point of the solvent and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

Next, the compound represented by the general formula [XII-3] is reacted with a thiocyanate and cyclized with a halogenating agent to give the compound represented by the general formula [XII-3]. Invention compounds can be prepared. As the thiocyanate, for example, sodium thiocyanate, potassium thiocyanate, ammonium thiocyanate and the like can be used. As the solvent, for example, halogenated hydrocarbons such as methylene chloride, chloroform or carbon tetrachloride, ethers such as diethyl ether, tetrahydrofuran or dioxane, hydrocarbons such as n-hexane, benzene or toluene, aliphatics such as acetone or methyl ethyl ketone Carboxylic acids such as ketones and acetic acid, or aprotic polar solvents such as acetonitrile, DMF, DMAC and DMSO can be used. The above reaction is-
The reaction is carried out at a temperature in the range of 10 ° C. to the boiling point of the solvent, usually 1 to 2
Finish in 4 hours. As the halogenating agent, for example, chlorine, bromine, phosphorus tribromide, thionyl bromide, thionyl chloride, hydrogen chloride or hydrogen bromide can be used. The above cyclization reaction is carried out in a range from room temperature to the boiling point of the solvent, and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

Next, the compound of the present invention represented by the general formula [XII-3] is reacted with a compound represented by the general formula [XII-4] in the presence of a base to obtain a compound of the general formula [XII-3] XII-5] can be produced. As a base, for example, an inorganic base such as sodium, sodium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogencarbonate or potassium hydrogencarbonate or triethylamine, DB
Organic amines such as U, pyridine, picoline or quinoline can be used. As the solvent, for example, halogenated hydrocarbons such as methylene chloride, chloroform or carbon tetrachloride, ethers such as diethyl ether, THF or dioxane, hydrocarbons such as n-hexane, benzene or toluene, aliphatics such as acetone or methyl ethyl ketone Carboxylic acids such as ketones and acetic acid, or aprotic polar solvents such as acetonitrile, DMF, DMAC and DMSO can be used. The above reaction is carried out in the range of -10 ° C to the boiling point of the solvent, and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

Next, the compound of the formula [XII-5] is reacted with the compound of the formula [XII-6] in the presence of a base to give the compound of the formula [XII-5].
II] can be produced. As a base, for example, sodium, sodium hydride,
Sodium hydroxide, potassium hydroxide, sodium carbonate,
An inorganic base such as potassium carbonate, sodium hydrogencarbonate or potassium hydrogencarbonate, or an organic amine such as triethylamine, DBU, pyridine, picoline or quinoline can be used. As the solvent, for example, halogenated hydrocarbons such as methylene chloride, chloroform or carbon tetrachloride, ethers such as diethyl ether, THF or dioxane, hydrocarbons such as n-hexane, benzene or toluene, aliphatics such as acetone or methyl ethyl ketone Carboxylic acids such as ketones and acetic acid, or aprotic polar solvents such as acetonitrile, DMF, DMAC and DMSO can be used. The above reaction is-
The reaction is carried out at a temperature in the range of 10 ° C. to the boiling point of the solvent, usually 1 to 2
Finish in 4 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

Next, the compound of the present invention represented by the general formula [XII-3] is subjected to diazotization, and in some cases, hydrolyzed by using a catalyst such as copper nitrate or copper oxide to give a compound of the general formula [XII-3]. The compound of the present invention represented by the formula [XIII-1] can be produced. As a diazotizing agent, for example, sodium nitrite is used, and as a solvent, for example, acetic acid, hydrochloric acid,
Sulfuric acid, water or mixtures thereof can be used.
The above reaction is carried out in the range of -10 ° C to the boiling point of the solvent, and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

Next, the compound of the formula [XIII-1] is halogenated to give the compound of the formula [XIII-1]
The compound of the present invention represented by III-2] can be produced. As the halogenating agent, for example, chlorine, bromine, phosphorus tribromide, thionyl bromide, thionyl chloride, hydrogen chloride or hydrogen bromide can be used. The above reaction is carried out in the range of room temperature to the boiling point of the solvent and is usually completed in 1 to 24 hours.
The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

Next, the compound of the present invention represented by the general formula [XIII-2] is reacted with a compound represented by the general formula [XIII-3] in the presence of a base to give a compound of the general formula [XIII-3] XIII] can be produced. As a base, for example, an inorganic base such as sodium, sodium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogencarbonate or potassium hydrogencarbonate or triethylamine, DB
Organic amines such as U, pyridine, picoline or quinoline can be used. As the solvent, for example, halogenated hydrocarbons such as methylene chloride, chloroform or carbon tetrachloride, ethers such as diethyl ether, THF or dioxane, hydrocarbons such as n-hexane, benzene or toluene, aliphatics such as acetone or methyl ethyl ketone Carboxylic acids such as ketones and acetic acid, or aprotic polar solvents such as acetonitrile, DMF, DMAC and DMSO can be used. The above reaction is carried out in the range of -10 ° C to the boiling point of the solvent, and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

Next, the compound of the present invention represented by the general formula [XII-3] is subjected to diazotization, and then a copper salt or the like is used. The compound of the present invention represented by the general formula [XIII-2] can be produced. As the diazotizing agent, for example, sodium nitrite, nitrite and the like can be used, and as the solvent, for example, acetic acid, hydrochloric acid, hydrobromic acid, sulfuric acid, water, acetonitrile or a mixture thereof can be used. As the copper salt, for example, copper chloride, copper bromide or the like can be used. The above reaction is carried out in the range of -10 ° C to the boiling point of the solvent, and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography. <Production method 10>

[0131]

Embedded image (Wherein, P, X, Y, R ⁵ , R ⁶ and R ²⁸ each have the same meaning as described above, and R ²⁹ represents an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, an alkoxyalkyl group, a haloalkyl group, Represents a haloalkenyl group, an alkylthioalkyl group, an alkylsulfonylalkyl group or an alkylsulfinylalkyl group.) By nitrating the compound represented by the general formula [XIV-1], the compound represented by the general formula [XIV-2] is obtained. Can be produced. As the nitrating agent, for example, nitric acid or fuming nitric acid, or a mixed acid of nitric acid or fuming nitric acid and sulfuric acid can be used. The above reaction is performed at -10 ° C.
To within the range of the boiling point of the solvent, and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

Next, the compound represented by the general formula [XIV-2] is reacted with the compound represented by the general formula [XIV-3] in the presence of a base to give the compound represented by the general formula [XIV-2]
-4] can be produced. As a base, for example, sodium, sodium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, an inorganic base such as sodium hydrogencarbonate or potassium hydrogencarbonate or triethylamine, DBU, pyridine,
Organic amines such as picoline or quinoline can be used. As the solvent, for example, halogenated hydrocarbons such as methylene chloride, chloroform or carbon tetrachloride, ethers such as diethyl ether, THF or dioxane,
hydrocarbons such as n-hexane, benzene or toluene,
Aliphatic ketones such as acetone or methyl ethyl ketone,
Carboxylic acids such as acetic acid or acetonitrile, DM
An aprotic polar solvent such as F, DMAC or DMSO can be used. The above reaction is carried out in the range of -10 ° C to the boiling point of the solvent, and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

Next, the compound of the present invention represented by the general formula [XIV] can be produced by reducing and cyclizing the compound represented by the general formula [XIV-4]. As the reducing agent, for example, iron or tin / hydrochloric acid can be used. Examples of the solvent include carboxylic acids such as acetic acid, hydrocarbons such as benzene and toluene, alcohols such as methanol and ethanol, and water. For example, hydrochloric acid or acetic acid can be used as the acid. The above reaction is carried out in the range of room temperature to the boiling point of the solvent and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

Next, the compound of the present invention represented by the general formula [XV-1] can be produced by reducing the compound represented by the general formula [XIV-2]. As the reducing agent, for example, iron or tin / hydrochloric acid can be used. Examples of the solvent include carboxylic acids such as acetic acid, hydrocarbons such as benzene and toluene, alcohols such as methanol and ethanol, and water. The above reaction is carried out at a temperature ranging from room temperature to the boiling point of the solvent.
Ends in ~ 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

Next, the compound represented by the general formula [XV-6] is produced by reacting the compound represented by the general formula [XV-1] with carbonyldiimidazole (CDI) or phosgene. Can be. As the solvent, for example, halogenated hydrocarbons such as methylene chloride, chloroform or carbon tetrachloride, ethers such as diethyl ether, THF or dioxane, hydrocarbons such as n-hexane, benzene or toluene, aliphatics such as acetone or methyl ethyl ketone Carboxylic acids such as ketones and acetic acid, or aprotic polar solvents such as acetonitrile, DMF, DMAC and DMSO can be used. The above reaction is carried out in the range of -10 ° C to the boiling point of the solvent,
Usually, it is completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

Next, the compound of the present invention represented by the general formula [XV-7] can be produced by halogenating the compound represented by the general formula [XV-6]. As the halogenating agent, for example, chlorine, bromine, phosphorus tribromide, thionyl bromide, thionyl chloride, hydrogen chloride or hydrogen bromide can be used. The above reaction is carried out in the range of room temperature to the boiling point of the solvent and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

Next, the compound of the present invention represented by the general formula [XV-7] is reacted with a compound represented by the general formula [XV-8] in the presence of a base to give the compound of the general formula [XV-7]. X
V] of the present invention.
As a base, for example, an inorganic base such as sodium, sodium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate or potassium hydrogen carbonate or an organic amine such as triethylamine, DBU, pyridine, picoline or quinoline, etc. Can be used. Halogenated hydrocarbons such as methylene chloride, chloroform or carbon tetrachloride as a solvent,
Ethers such as diethyl ether, THF or dioxane; hydrocarbons such as n-hexane, benzene or toluene; aliphatic ketones such as acetone or methyl ethyl ketone; carboxylic acids such as acetic acid; or acetonitrile;
An aprotic polar solvent such as MF, DMAC or DMSO can be used. The above reaction is performed at -10 ° C.
To within the range of the boiling point of the solvent, and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

Next, the compound of the present invention represented by the general formula [XV-2] can be produced by reacting the compound of the present invention represented by the general formula [XV-1] with a xanthate. . As the xanthate, for example, sodium xanthate, potassium xanthate, ammonium xanthate and the like can be used. As the solvent, for example, carboxylic acids such as acetic acid, hydrocarbons such as benzene or toluene, alcohols such as methanol or ethanol, water, or a mixture thereof can be used. The above reaction is carried out in the range of -10 ° C to the boiling point of the solvent, and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

Next, the compound of the present invention represented by the general formula [XV-2] is reacted with the compound represented by the general formula [XV-3] in the presence of a base.
The compound of the present invention represented by 4) can be produced.
As a base, for example, an inorganic base such as sodium, sodium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate or potassium hydrogen carbonate or an organic amine such as triethylamine, DBU, pyridine, picoline or quinoline, etc. Can be used. As a solvent, for example, dichloromethane,
Halogenated hydrocarbons such as chloroform or carbon tetrachloride, ethers such as diethyl ether, THF or dioxane, hydrocarbons such as n-hexane, benzene or toluene, aliphatic ketones such as acetone or methyl ethyl ketone or acetonitrile, DMF , Aprotic polar solvents such as DMAC or DMSO, and the like. The above reaction is carried out in the range of -10 ° C to the boiling point of the solvent, and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

Next, the compound of the present invention represented by the general formula [XV-5] can be produced by oxidizing the compound of the present invention represented by the general formula [XV-4]. As the oxidizing agent, for example, hydrogen peroxide, m-chloroperbenzoic acid, sodium hypochlorite, potassium peroxide monosulfate (trade name Oxone) and the like can be used. As a solvent, for example, halogenated hydrocarbons such as dichloromethane, chloroform or carbon tetrachloride, hydrocarbons such as n-hexane, benzene or toluene, aliphatic ketones such as acetone or methyl ethyl ketone or protic such as methanol, ethanol or water Polar solvents and the like can be used. The above reaction is carried out in the range of -10 ° C to the boiling point of the solvent, and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

Next, the compound of the present invention represented by the general formula [XV-8] is reacted with a compound represented by the general formula [XV-8] in the presence of a base to give a compound of the general formula [XV-5]. X
V] of the present invention.
As a base, for example, an inorganic base such as sodium, sodium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate or potassium hydrogen carbonate or an organic amine such as triethylamine, DBU, pyridine, picoline or quinoline, etc. Can be used. Halogenated hydrocarbons such as methylene chloride, chloroform or carbon tetrachloride as a solvent,
Ethers such as diethyl ether, THF or dioxane; hydrocarbons such as n-hexane, benzene or toluene; aliphatic ketones such as acetone or methyl ethyl ketone; carboxylic acids such as acetic acid; or acetonitrile;
An aprotic polar solvent such as MF, DMAC or DMSO can be used. The above reaction is carried out in the range of normal pressure to 20 atm, -10 ° C to 200 ° C,
Usually, it is completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography. <Production method 11>

[0142]

Embedded image (Wherein, P, X, Y, R ⁵ , R ⁶ , R ^{22 ′} and R ²⁷
Represents the same meaning as described above. The compound of the present invention represented by the general formula [XVI-2] can be produced by brominating the compound of the present invention represented by the general formula [XVI-1]. For example, NBS or the like can be used as the brominating agent. For example, 2,2'-azobisisobutyronitrile can be used as a catalyst. As the solvent, for example, halogenated hydrocarbons such as carbon tetrachloride and the like can be used. The above reaction is optionally carried out in a range of -10 ° C to the boiling point of the solvent under a nitrogen stream, and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

Next, the compound of the general formula [XVI-2] is reacted with the compound of the general formula [XVI-3] in the presence of a base to give the compound of the general formula [XVI-2]
The compound of the present invention represented by I] can be produced.
As the base, for example, an inorganic base such as sodium, sodium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate or potassium carbonate can be used.
As a solvent, for example, ethers such as diethyl ether, THF or dioxane, hydrocarbons such as n-hexane, benzene or toluene, aliphatic ketones such as acetone or methyl ethyl ketone, acetonitrile, DMF, DMA
An aprotic polar solvent such as C or DMSO or an excess of the compound represented by the general formula [XVI-3] can be used. The above reaction is optionally carried out under a nitrogen stream at a temperature ranging from -10 ° C to the boiling point of the solvent.
Ends in ~ 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

Next, the compound of the formula [XVIII-2] is reacted with the compound of the formula [XVIII-1] in the presence of a base to give the compound of the formula [XVIII] Can be produced. As the base, for example, an inorganic base such as sodium, sodium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate or potassium carbonate can be used. As a solvent, for example, diethyl ether, THF
Or ethers such as dioxane, hydrocarbons such as n-hexane, benzene or toluene, aliphatic ketones such as acetone or methyl ethyl ketone, or aprotic polar solvents such as acetonitrile, DMF, DMAC or DMSO. it can. The above reaction is-
The reaction is carried out at a temperature in the range of 10 ° C. to the boiling point of the solvent, usually 1 to 2
Finish in 4 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

Next, the compound of the present invention represented by the general formula [XVII] is oxidized to oxidize the compound of the general formula [XVII].
I '] or a compound of the general formula [XVII
I "]. The oxidizing agent may be, for example, hydrogen peroxide, metachloroperbenzoic acid, sodium hypochlorite or potassium monosulfate (trade name Oxone). Examples of the solvent include halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, ethers such as diethyl ether, THF and dioxane, hydrocarbons such as n-hexane, benzene and toluene, and fats such as acetone and methyl ethyl ketone. Aromatic ketones, acetonitrile, DMF, DM
An aprotic polar solvent such as AC or DMSO or a protic polar solvent such as methanol, ethanol or water can be used. The above reaction is carried out in the range of room temperature to the boiling point of the solvent and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

Next, the compound of the formula [XVI-2] is reacted with the compound of the formula [XVII-1] in the presence of a base to give the compound of the formula [XVI-2].
VII] can be produced. As a base, for example, sodium, sodium hydride,
Inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate or potassium carbonate can be used. Examples of the solvent include ethers such as diethyl ether, THF or dioxane, hydrocarbons such as n-hexane, benzene or toluene, aliphatic ketones such as acetone or methyl ethyl ketone, acetonitrile, DMF, D
An aprotic polar solvent such as MAC or DMSO or an excess of the compound represented by the general formula [XVII-1] can be used. The above reaction is optionally carried out in a range of -10 ° C to the boiling point of the solvent under a nitrogen stream, and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography. <Production method 12>

[0147]

Embedded image (In the formula, P, R ⁵ , R ⁶ and R ²⁹ each have the same meaning as described above.) A compound represented by the general formula [XIX-1] is reacted with a Lewis acid to form a compound represented by the general formula [XIX] Can be produced. As the Lewis acid, for example, aluminum chloride or titanium tetrachloride can be used. As the solvent, for example, halogenated hydrocarbons such as methylene chloride, chloroform or carbon tetrachloride, ethers such as diethyl ether, tetrahydrofuran or dioxane, hydrocarbons such as n-hexane, benzene or toluene can be used. The above reaction is -10
The reaction is carried out at a temperature in the range of from 0 ° C to the boiling point of the solvent, and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography. <Production method 13>

[0148]

Embedded image (Wherein, P, R ⁵ and R ⁶ each have the same meaning as described above, and R ³⁰ represents an alkyl group.) A compound represented by the general formula [XX-1] is reacted with an oxidizing agent, The compound represented by the general formula [XX-2] can be produced. Jones reagent (Cr
O ₃ —H ₂ SO ₄ ) and the like can be used. As the solvent, for example, halogenated hydrocarbons such as methylene chloride, chloroform or carbon tetrachloride, ethers such as diethyl ether, tetrahydrofuran or dioxane, hydrocarbons such as n-hexane, benzene or toluene, aliphatics such as acetone or methyl ethyl ketone Solvents such as ketones and carboxylic acids such as acetic acid can be used. The above reaction is carried out in a temperature range from -20 ° C to the boiling point of the solvent, and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method.

Next, the compound of the present invention represented by the formula [XX-2] is reacted with a halogenating agent to give a compound of the formula [XX-XX].
3] can be produced. As the halogenating agent, thionyl chloride, phosphorus trichloride, phosphorus pentachloride and the like can be used. As the solvent, for example, halogenated hydrocarbons such as methylene chloride, chloroform or carbon tetrachloride, ethers such as diethyl ether, tetrahydrofuran or dioxane, hydrocarbons such as n-hexane, benzene or toluene, aliphatics such as acetone or methyl ethyl ketone Carboxylic acids such as ketones and acetic acid, or aprotic polar solvents such as acetonitrile, DMF, DMAC and DMSO can be used. The above reaction is carried out in the range of -10 ° C to the boiling point of the solvent, and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method.

The compound of the present invention represented by the general formula [XX] can be produced by reacting the compound represented by the general formula [XX-2] with an organometallic reagent. As the organometallic reagent, a Grignard reagent, an organolithium reagent or the like can be used. As a solvent, for example, ethers such as diethyl ether, tetrahydrofuran or dioxane, hydrocarbons such as n-hexane, benzene or toluene, or acetonitrile, DMF,
An aprotic polar solvent such as DMAC or DMSO can be used. The above reaction is carried out in a temperature range from -70 ° C to the boiling point of the solvent, and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography. <Production method 14>

[0151]

Embedded image (Wherein, P, R ⁵ , R ⁶ , R ²³ , R ²⁴ and R ²⁷ each have the same meaning as described above, and R ³¹ represents an alkyl group,
Represents an alkenyl group, an alkynyl group, or an optionally substituted phenyl group. ) The compound represented by the general formula [XXI-1] and the general formula [XX]
I-2] to give a compound of the general formula [X
XI] can be produced. As a solvent, for example, ethers such as diethyl ether, tetrahydrofuran or dioxane, n-hexane,
Hydrocarbons such as benzene or toluene, aliphatic ketones such as acetone or methyl ethyl ketone, or aprotic polar solvents such as acetonitrile, DMF, DMAC or DMSO can be used. The above reaction is carried out in the range of -10 ° C to the boiling point of the solvent, and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

Next, the compound represented by the general formula [XXI-1] is reacted with the compound represented by the general formula [XXI-3] to give the compound of the present invention represented by the general formula [XXI ']. Can be manufactured. As the solvent, for example, acids such as concentrated sulfuric acid can be used. The above reaction is carried out in a temperature range from -20 ° C to the boiling point of the solvent, and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography. <Production method 15>

[0153]

Embedded image (Wherein, P, R ⁵ , R ⁶ and Y each have the same meaning as described above, and R ³² and R ³³ each represent a C ₁ -C ₅ alkyl group.) Formula (XXII-1) Compound and general formula [X
XII-2] in the presence of anhydrous magnesium bromide to give a compound of the general formula [XXI
The compound of the present invention represented by I] can be produced.
Examples of the solvent include ethers such as diethyl ether, THF and dioxane, hydrocarbons such as n-hexane, benzene and toluene, acetonitrile, DM
An aprotic polar solvent such as F, DMAC or DMSO can be used. The above reaction is carried out in the range of -10 ° C to the boiling point of the solvent, and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography. <Production method 16>

[0154]

Embedded image (Wherein, P, R ⁵ , R ⁶ , R ³² , R ³³ , X and Y each have the same meaning as described above.) The compound of the present invention represented by the general formula [XXIII-1] is present in the presence of a reducing agent. By reduction under the general formula [XXI
The compound of the present invention represented by II-2] can be produced. As the solvent, for example, alcohols such as methanol and ethanol, ethers such as diethyl ether, THF and dioxane, and hydrocarbons such as n-hexane, benzene and toluene can be used. As the reducing agent, for example, lithium aluminum hydride, sodium boron hydride and the like can be used. The above reaction is carried out in the range of -10 ° C to the boiling point of the solvent, and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method.
Further, if necessary, purification is performed by recrystallization or column chromatography.

Next, the compound of the formula [XXIII-2] is reacted with the compound of the formula [XXIII-3] in the presence of a base to give the compound of the formula [XXIII]. Can be produced. As a solvent, for example, diethyl ether, TH
Use ethers such as F or dioxane, hydrocarbons such as n-hexane, benzene or toluene, aliphatic ketones such as acetone or methyl ethyl ketone, or aprotic polar solvents such as acetonitrile, DMF, DMAC or DMSO. be able to. The above reaction is
The reaction is carried out in the range of -10 ° C to the boiling point of the solvent, usually 1 to
Ends in 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography. <Production method 17>

[0156]

Embedded image (In the formula, P, X, Y, R ⁵ , R ⁶ , R ²⁸ and R ²⁹ each have the same meaning as described above.) The compound of the present invention represented by the general formula [XXIV-1] is replaced with a Lewis acid or the like. By reacting, the general formula [XXIV-
The compound of the present invention represented by 2) can be produced.
As the Lewis acid, for example, aluminum chloride, titanium tetrachloride, boron tribromide and the like can be used. As the solvent, for example, halogenated hydrocarbons such as dichloromethane, chloroform or carbon tetrachloride, and hydrocarbons such as n-hexane, benzene or toluene can be used. The above reaction is carried out in a temperature range from -70 ° C to the boiling point of the solvent, and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

Next, the compound of the present invention represented by the general formula [XXIV-2] is reacted with the compound represented by the general formula [XXIV-3] in the presence of a base. The compound of the present invention represented by 4) can be produced. As a base, for example, an inorganic base such as sodium, sodium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogencarbonate or potassium hydrogencarbonate or triethylamine;
Organic amines such as BU, pyridine, picoline and quinoline can be used. As the solvent, for example, halogenated hydrocarbons such as dichloromethane, chloroform or carbon tetrachloride, ethers such as diethyl ether, THF or dioxane, hydrocarbons such as n-hexane, benzene or toluene, aliphatic ketones such as acetone or methyl ethyl ketone Or acetonitrile, DMF, D
An aprotic polar solvent such as MAC or DMSO can be used. The above reaction is carried out in the range of -10 ° C to the boiling point of the solvent, and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

Next, the present compound represented by the general formula [XXIV-4] is reduced and cyclized to give a compound of the general formula [XIV-4]
XIV-5] can be produced. As the reducing agent, for example, iron or tin / hydrochloric acid can be used. Examples of the solvent include carboxylic acids such as acetic acid, hydrocarbons such as benzene and toluene, alcohols such as methanol and ethanol, and water. For example, hydrochloric acid or acetic acid can be used as the acid. The above reaction is carried out in the range of room temperature to the boiling point of the solvent and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

Next, the compound of the general formula [XXIV-1] is reduced by reducing the compound of the present invention represented by the general formula [XXIV-1].
-6] can be produced. As the reducing agent, for example, iron or tin / hydrochloric acid can be used. Examples of the solvent include carboxylic acids such as acetic acid, hydrocarbons such as benzene and toluene, alcohols such as methanol and ethanol, and water. The above reaction is carried out in the range of room temperature to the boiling point of the solvent and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method.

Next, the compound of the present invention represented by the general formula [XXIV-7] can be produced by reacting the compound of the present invention represented by the general formula [XXIV-6] with a Lewis acid or the like. As the Lewis acid, for example, aluminum chloride, titanium tetrachloride, boron tribromide and the like can be used. As the solvent, for example, halogenated hydrocarbons such as dichloromethane, chloroform or carbon tetrachloride, and hydrocarbons such as n-hexane, benzene or toluene can be used. The above reaction is carried out in a temperature range from -70 ° C to the boiling point of the solvent, and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Also,
Purify by recrystallization or column chromatography as needed.

Next, the compound of the present invention represented by the general formula [XXIV-7] and carbonyldiimidazole (CDI)
Or by reacting with phosgene to obtain a compound of the general formula [XX
The compound of the present invention represented by IV-8] can be produced. As the solvent, for example, halogenated hydrocarbons such as dichloromethane, chloroform or carbon tetrachloride, ethers such as diethyl ether, THF or dioxane, hydrocarbons such as n-hexane, benzene or toluene, aliphatic ketones such as acetone or methyl ethyl ketone Or an aprotic polar solvent such as acetonitrile, DMF, DMAC or DMSO. The above reaction is carried out in the range of -10 ° C to the boiling point of the solvent,
Usually, it is completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

Next, the compound of the present invention represented by the general formula [XIV-8] is halogenated to give the compound of the general formula [XIV-8]
XIV-9] can be produced. As the halogenating agent, for example, chlorine, bromine, phosphorus tribromide, thionyl bromide, thionyl chloride, hydrogen chloride or hydrogen bromide can be used. As the solvent, for example, halogenated hydrocarbons such as dichloromethane, chloroform or carbon tetrachloride, and hydrocarbons such as n-hexane, benzene or toluene can be used. The above reaction is carried out in the range of room temperature to the boiling point of the solvent and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

Next, the compound of the present invention represented by the general formula [XXV-10] can be produced by reacting the compound of the present invention represented by the general formula [XXIV-7] with a xanthate salt or the like. . As the xanthate, for example, sodium xanthate, potassium xanthate, ammonium xanthate and the like can be used. As the solvent, for example, carboxylic acids such as acetic acid, hydrocarbons such as benzene or toluene, alcohols such as methanol or ethanol, water, or a mixture thereof can be used. The above reaction is carried out in the range of -10 ° C to the boiling point of the solvent, and is usually completed in 1 to 24 hours.
The above cyclization reaction is carried out in a range from room temperature to the boiling point of the solvent, and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

Next, the compound of the formula [XXV-10] is reacted with the compound of the formula [XV-3] in the presence of a base to give the compound of the formula [XIV-10].
XIV-11] can be produced. As a base, for example, an inorganic base such as sodium, sodium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogencarbonate or potassium hydrogencarbonate or triethylamine, DB
Organic amines such as U, pyridine, picoline or quinoline can be used. As the solvent, for example, halogenated hydrocarbons such as dichloromethane, chloroform or carbon tetrachloride, ethers such as diethyl ether, THF or dioxane, hydrocarbons such as n-hexane, benzene or toluene, aliphatic ketones such as acetone or methyl ethyl ketone Or acetonitrile, DMF, DM
An aprotic polar solvent such as AC or DMSO can be used. The above reaction is carried out in the range of -10 ° C to the boiling point of the solvent, and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

Next, the compound of the general formula [XXI-11] is oxidized to oxidize the compound of the present invention [XXI-11].
V-12] can be produced. As the oxidizing agent, for example, hydrogen peroxide, m-chloroperbenzoic acid, sodium hypochlorite, potassium peroxide monosulfate (trade name Oxone) and the like can be used. As a solvent, for example, halogenated hydrocarbons such as dichloromethane, chloroform or carbon tetrachloride, ethers such as diethyl ether, THF or dioxane, hydrocarbons such as n-hexane, benzene or toluene, or protons such as methanol, ethanol or water A polar solvent or the like can be used. The above reaction is carried out in the range of -10 ° C to the boiling point of the solvent, and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

Next, the compounds represented by the general formulas [XXIV-9], [XXI
V-12] and a compound of the general formula [XV-
The compound of the present invention represented by the general formula [XXIV] can be produced by reacting the compound represented by the formula [8] in the presence of a base. As a base, for example, sodium,
It is possible to use an inorganic base such as sodium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate or potassium hydrogen carbonate or an organic amine such as triethylamine, DBU, pyridine, picoline or quinoline. it can. As a solvent, for example, halogenated hydrocarbons such as dichloromethane, chloroform or carbon tetrachloride, diethyl ether, THF
Or ethers such as dioxane, hydrocarbons such as n-hexane, benzene or toluene, aliphatic ketones such as acetone or methyl ethyl ketone, or aprotic polar solvents such as acetonitrile, DMF, DMAC or DMSO. it can. The above reaction is-
The reaction is carried out at a temperature in the range of 10 ° C. to the boiling point of the solvent, usually 1 to 2
Finish in 4 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography. <Production method 18>

[0167]

Embedded image (Wherein, P and R ⁵ each have the same meaning as described above,
R ³⁴ represents an alkyl group, a cycloalkyl group, an alkynyl group, an alkoxyalkyl group, an alkoxycarbonylalkyl group or an alkenyl group; ^{R34 ′} represents an alkyl group, a cycloalkyl group, an alkynyl group, an alkoxyalkyl group, an alkoxycarbonylalkyl group or Represents an alkenyl group. The compound of the present invention represented by the general formula [XXV-2] can be produced by reducing the compound of the present invention represented by the general formula [XXV-1]. As the reducing agent, for example, iron or tin / hydrochloric acid can be used. Examples of the solvent include carboxylic acids such as acetic acid, esters such as ethyl acetate, hydrocarbons such as benzene and toluene, alcohols such as methanol and ethanol, and water. The above reaction is carried out in the range of room temperature to the boiling point of the solvent and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

Next, by reacting the obtained compound represented by the general formula [XXV-2] with a cyanating agent,
The compound represented by the general formula [XXV-3] can be produced. As the cyanating agent, for example, copper cyanide or zinc cyanide can be used. If necessary, potassium iodide, tetrakistriphenylphosphine palladium, or the like can be used as a reaction catalyst. Examples of the solvent include ethers such as diethyl ether, THF or dioxane, hydrocarbons such as n-hexane, benzene or toluene, alcohols such as methanol or ethanol, acetonitrile, N, N-dimethylformamide (DMF) or N, N -Dimethyl-2
Aprotic polar solvents such as imidazolidinone (DMI) and the like can be used. The above reaction is optionally carried out in a range of -10 ° C to the boiling point of the solvent under a nitrogen stream, and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Also,
Purify by recrystallization or column chromatography as needed.

Next, the resulting compound of the general formula [XXV-3] is reacted with the compound of the general formula [XXV-4] in the presence of a base to give the compound of the general formula [XXV-3]. The compound of the present invention represented by [XXV-6] can be produced. As a base, for example, an inorganic base such as sodium, sodium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogencarbonate or potassium hydrogencarbonate or triethylamine;
Organic amines such as BU, pyridine, picoline and quinoline can be used. As the solvent, for example, halogenated hydrocarbons such as dichloromethane, chloroform or carbon tetrachloride, ethers such as diethyl ether, THF or dioxane, hydrocarbons such as n-hexane, benzene or toluene, aliphatic ketones such as acetone or methyl ethyl ketone Or an aprotic polar solvent such as acetonitrile, DMF or DMI. The above reaction is carried out in the range of room temperature to the boiling point of the solvent and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

As another method, the compound of the general formula [XXV-2] is reacted with the compound of the general formula [XXV-4] in the presence of a base to give the compound of the general formula [XXV-2]. -5] of the present invention. As a base, for example, an inorganic base such as sodium, sodium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogencarbonate or potassium hydrogencarbonate or triethylamine;
Organic amines such as BU, pyridine, picoline and quinoline can be used. As the solvent, for example, halogenated hydrocarbons such as dichloromethane, chloroform or carbon tetrachloride, ethers such as diethyl ether, THF or dioxane, hydrocarbons such as n-hexane, benzene or toluene, aliphatic ketones such as acetone or methyl ethyl ketone Or an aprotic polar solvent such as acetonitrile, DMF or DMI. The above reaction is carried out in the range of room temperature to the boiling point of the solvent and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

Next, by reacting the obtained compound represented by the general formula [XXV-5] with a cyanating agent,
The compound represented by the general formula [XXV-6] can be produced. As the cyanating agent, for example, copper cyanide or zinc cyanide can be used. If necessary, potassium iodide, tetrakistriphenylphosphine palladium, or the like can be used as a reaction catalyst. As the solvent, for example, ethers such as diethyl ether, THF or dioxane, hydrocarbons such as n-hexane, benzene or toluene, alcohols such as methanol or ethanol, or acetonitrile, DMF or D
An aprotic polar solvent such as MI can be used. The above reaction is optionally carried out under a nitrogen stream at -1.
The reaction is carried out at a temperature ranging from 0 ° C. to the boiling point of the solvent, usually from 1 to 24.
End in time. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

Next, the resulting compound of the present invention represented by the general formula [XXV-3] is reacted with the compound represented by the general formula [XXV-4] in the presence of a base to give a compound of the general formula [XXV-4]. The compound of the present invention represented by [XXV] can be produced. As a base, for example, an inorganic base such as sodium, sodium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogencarbonate or potassium hydrogencarbonate or triethylamine, DB
Organic amines such as U, pyridine, picoline or quinoline can be used. As the solvent, for example, halogenated hydrocarbons such as dichloromethane, chloroform or carbon tetrachloride, ethers such as diethyl ether, THF or dioxane, hydrocarbons such as n-hexane, benzene or toluene, aliphatic ketones such as acetone or methyl ethyl ketone Or acetonitrile, DMF or D
An aprotic polar solvent such as MI can be used. The above reaction is carried out in the range of room temperature to the boiling point of the solvent and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

Next, the resulting compound of the present invention represented by the general formula [XXV-6] is reacted with the compound represented by the general formula [XXV-7] in the presence of a base to give a compound of the general formula [XXV-6]. XXV '] can be produced. As a base, for example, an inorganic base such as sodium, sodium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogencarbonate or potassium hydrogencarbonate or triethylamine, DB
Organic amines such as U, pyridine, picoline or quinoline can be used. As the solvent, for example, halogenated hydrocarbons such as dichloromethane, chloroform or carbon tetrachloride, ethers such as diethyl ether, THF or dioxane, hydrocarbons such as n-hexane, benzene or toluene, aliphatic ketones such as acetone or methyl ethyl ketone Or acetonitrile, DMF or D
An aprotic polar solvent such as MI can be used. The above reaction is carried out in the range of room temperature to the boiling point of the solvent and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography. <Production method 19>

[0174]

Embedded image (Wherein, P, R ⁵ , R ¹⁶ and R ³⁴ each have the same meaning as described above, and R ³⁵ represents an alkyl group.) The compound of the present invention represented by the general formula [XXVI-1] and a Lewis acid To produce the compound of the present invention represented by the general formula [XXVI-2]. As the Lewis acid, for example, boron tribromide or aluminum chloride can be used. As a solvent, for example, halogenated hydrocarbons such as dichloromethane, chloroform or carbon tetrachloride,
Hydrocarbons such as n-hexane, benzene or toluene, or aliphatic ketones such as acetone or methyl ethyl ketone can be used. The above reaction is -1
The reaction is carried out at a temperature within the range of from 00 ° C. to the boiling point of the solvent, usually from 1 to 2
Finish in 4 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

Next, the compound of the present invention represented by the general formula [XXVI-2] is reacted with the compound represented by the general formula [XXVI-3] in the presence of a base, or
VI-4] and a compound represented by the general formula [XXVI-
The compound of the present invention represented by the general formula [XXVI-6] can be produced by reacting the compound represented by the formula [5] with triphenylphosphine. As a base, for example, organic amines such as triethylamine, DBU, pyridine, picoline or quinoline or sodium methoxide, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium acetate, potassium acetate, sodium hydrogen carbonate Alternatively, an inorganic base such as potassium bicarbonate can be used. As the solvent, for example, halogenated hydrocarbons such as dichloromethane, chloroform or carbon tetrachloride, ethers such as diethyl ether, THF or dioxane, hydrocarbons such as n-hexane, benzene or toluene, aliphatic ketones such as acetone or methyl ethyl ketone , Carboxylic acids such as acetic acid or acetonitrile, D
An aprotic polar solvent such as MF or DMI can be used. The above reaction is carried out in the range of room temperature to the boiling point of the solvent and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method.
Further, if necessary, purification is performed by recrystallization or column chromatography.

Next, the compound of the present invention represented by the general formula [XXVI] can be produced by reacting the obtained compound represented by the general formula [XXVI-6] with a cyanating agent. . As the cyanating agent, for example, copper cyanide or zinc cyanide can be used. If necessary, potassium iodide, tetrakistriphenylphosphine palladium, or the like can be used as a reaction catalyst. As a solvent, for example, diethyl ether, THF
Or ethers such as dioxane, hydrocarbons such as n-hexane, benzene or toluene, alcohols such as methanol or ethanol or acetonitrile, DMF
Alternatively, an aprotic polar solvent such as DMI can be used. The above reaction is optionally carried out under a nitrogen stream at a temperature ranging from -10 ° C to the boiling point of the solvent.
Ends in ~ 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

As another method, the compound represented by the general formula [XXVI-1]
By reacting the compound represented by the formula with a cyanating agent, a compound represented by the general formula [XXVI-7] can be produced. As the cyanating agent, for example, copper cyanide or zinc cyanide can be used. If necessary, potassium iodide, tetrakistriphenylphosphine palladium, or the like can be used as a reaction catalyst. As the solvent, for example, ethers such as diethyl ether, THF or dioxane, hydrocarbons such as n-hexane, benzene or toluene, alcohols such as methanol or ethanol, or aprotic polar solvents such as acetonitrile, DMF or DMI are used. can do. The above reaction may be carried out in a range of from −10 ° C. to the boiling point of the solvent under a nitrogen stream in some cases.
Ends in 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

Next, the compound of the present invention represented by the general formula [XXVI-8] is produced by reacting the obtained compound of the general formula [XXVI-7] with a Lewis acid. Can be. As the Lewis acid, for example, boron tribromide or aluminum chloride can be used. As the solvent, for example, halogenated hydrocarbons such as dichloromethane, chloroform or carbon tetrachloride, hydrocarbons such as n-hexane, benzene or toluene, and aliphatic ketones such as acetone or methyl ethyl ketone can be used. The above reaction is carried out in a temperature range from -100 ° C to the boiling point of the solvent, and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

Next, the compound of the present invention represented by the general formula [XXVI-8] is reacted with the compound represented by the general formula [XXVI-3] in the presence of a base, or the compound of the general formula [XXVI-8]
VI-4] and a compound represented by the general formula [XXVI-
The compound of the present invention represented by the general formula [XXVI] can be produced by reacting the compound represented by the formula [5] with triphenylphosphine. As a base, for example, organic amines such as triethylamine, DBU, pyridine, picoline or quinoline or sodium methoxide, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium acetate, potassium acetate, sodium hydrogen carbonate Alternatively, an inorganic base such as potassium bicarbonate can be used. As a solvent, for example, halogenated hydrocarbons such as dichloromethane, chloroform or carbon tetrachloride, ethers such as diethyl ether, THF or dioxane,
hydrocarbons such as n-hexane, benzene or toluene,
Aliphatic ketones such as acetone or methyl ethyl ketone,
Carboxylic acids such as acetic acid or acetonitrile, DMF
Alternatively, an aprotic polar solvent such as DMI can be used. The above reaction is carried out in the range of room temperature to the boiling point of the solvent and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography. <Production method 20>

[0180]

Embedded image (In the formula, P, R ⁵ , R ³⁴ and Y each have the same meaning as described above.) By reacting the compound represented by the general formula [XXVII-1] with a cyanating agent, the compound represented by the general formula [XXVII] −
2] can be produced. As the cyanating agent, for example, copper cyanide or zinc cyanide can be used. If necessary, potassium iodide, tetrakistriphenylphosphine palladium, or the like can be used as a reaction catalyst. Examples of the solvent include ethers such as diethyl ether, THF and dioxane, hydrocarbons such as n-hexane, benzene and toluene, alcohols such as methanol and ethanol, and aprotic polar solvents such as acetonitrile, DMF, DMSO and DMI. Can be used. The above reaction is optionally carried out in a range of -10 ° C to the boiling point of the solvent under a nitrogen stream, and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography.

Next, the obtained compound of the formula [XXVII-2] is reacted with the compound of the formula [XXVII-3] in the presence of a base to give the compound of the formula [XXVII]. The compounds of the present invention represented can be prepared. As a base, for example, triethylamine, DB
Organic amines such as U, pyridine, picoline or quinoline, or sodium methoxide, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium acetate, potassium acetate, sodium hydrogen carbonate or potassium hydrogen carbonate, etc. And the like. As the solvent, for example, halogenated hydrocarbons such as dichloromethane, chloroform or carbon tetrachloride, ethers such as diethyl ether, THF or dioxane, hydrocarbons such as n-hexane, benzene or toluene, aliphatic ketones such as acetone or methyl ethyl ketone , Carboxylic acids such as acetic acid, or aprotic polar solvents such as acetonitrile, DMF and DMI. The above reaction is carried out in the range of room temperature to the boiling point of the solvent and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Further, if necessary, purification is performed by recrystallization or column chromatography. <Production method 21>

[0182]

Embedded image (Wherein, P, R ⁵ and R ⁶ each have the same meaning as described above, and R ³⁶ represents an alkyl group, an alkenyl group, an alkynyl group or a cycloalkyl group.) Represented by the general formula [XXVIII-1] The compound of the present invention represented by the general formula [XXVIII] can be produced by reacting the compound of the present invention with a phosphite or the like. As the solvent, for example, halogenated hydrocarbons such as dichloromethane, chloroform or carbon tetrachloride, ethers such as diethyl ether, THF or dioxane, hydrocarbons such as n-hexane, benzene or toluene, aliphatic ketones such as acetone or methyl ethyl ketone Or acetonitrile, DMF, DMAC or DM
An aprotic polar solvent such as SO can be used. The above reaction is carried out in the range of -10 ° C to the boiling point of the solvent, and is usually completed in 1 to 24 hours. The target compound can be isolated from the reaction solution by a conventional method. Also,
Purify by recrystallization or column chromatography as needed.

[0183]

EXAMPLES Next, the production method, formulation method and use of the compound of the present invention will be specifically described with reference to examples. However, the invention is not limited to these specific examples. First, specific production examples of the compound of the present invention will be described.

<Production Example 1> 3- (4-Chloro-2-fluoro-5-acetonyloxyphenyl) -1-methyl-6-trifluoromethyl-
Production of 2 (1H) -pyridone (Compound No. 1-2) 3- (4-chloro-2-fluoro-5-hydroxyphenyl) -1-methyl-6-trifluoromethyl-2 (1
H) -Pyridone (1.00 g, 3.11 mmol) was dissolved in acetonitrile (30 ml), and chloroacetone (0.32) was dissolved.
g (3.46 mmol) and 0.52 g of potassium carbonate
(3.76 mmol) was added and the mixture was heated under reflux for 2 hours. After removing insoluble matter by filtration, the solvent was distilled off under reduced pressure, extracted with ethyl acetate, and the organic layer was washed with water. After drying over anhydrous magnesium sulfate, the residue obtained by evaporating the solvent under reduced pressure is isolated and purified by silica gel column chromatography (hexane: ethyl acetate = 3: 1) to obtain the desired product 1.1.
0 g (94% yield) was obtained. 128-129 ° C

<Production Example 2> 3- [7-Chloro-5-fluoro-2- (1-methylaminoethyl) benzofuran-4-yl] -1-methyl-
Production of 6-trifluoromethyl-2 (1H) -pyridone (Compound No. 2-1) 3- [7-chloro-5-fluoro-2- (1-bromoethyl) benzofuran-4-yl] -1-methyl- 6-trifluoromethyl-2 (1H) -pyridone 0.30 g
(0.66 mmol) was dissolved in 5 ml of acetonitrile, and 0.10 g (1.3 mm
ol) and stirred overnight. The solvent was concentrated under reduced pressure,
The mixture was extracted with ethyl acetate, and the organic layer was washed with water. After drying over anhydrous magnesium sulfate, the residue obtained by evaporating the solvent under reduced pressure was isolated and purified by silica gel column chromatography (hexane: ethyl acetate: triethylamine = 2: 1: 0.2) to obtain 0.22 g of the desired product (yield). 82%). ¹ H-NMR (300 MHz, CDCl ₃ ) δ value: 1.
49 (3H, d), 1.63 (1H, bs), 2.40
(3H, s), 3.73 (3H, s), 3.89 (1
H, q), 6.45 (1H, s), 6.80 (1H,
d), 7.11 (1H, d), 7.54 (1H, d) p
pm

<Production Example 3> 3- [7-Chloro-5-fluoro-2- (1-acetylaminoethyl) benzofuran-4-yl] -1-methyl-6-trifluoromethyl-2 (1H)- Production of pyridone (Compound No. 2-6) 3- [7-chloro-5-fluoro-2- (1-bromoethyl) benzofuran-4-yl] -1-methyl-6-trifluoromethyl-2 (1H)- Pyridone 0.50g
(1.1 mmol) was dissolved in 5 ml of concentrated sulfuric acid, 0.45 g (11 mmol) of acetonitrile was added, and the mixture was stirred overnight. The reaction solution was poured into ice water, extracted with ethyl acetate, and washed with an aqueous sodium hydrogen carbonate solution. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the residue was subjected to silica gel column chromatography (hexane: ethyl acetate:
= 1: 1) and 0.12 g of the desired product (yield 25
%). 74-76 ° C

<Production Example 4> 3- [7-Chloro-5-fluoro-2- (1-N, N-
Dimethylcarbamoyloxyethyl) benzofuran-4
-Yl] -1-methyl-6-trifluoromethyl-2
Production of (1H) -pyridone (Compound No. 2-10) 3- [7-chloro-5-fluoro-2- (1-hydroxyethyl) benzofuran-4-yl] -1-methyl-6
-Trifluoromethyl-2 (1H) -pyridone 0.40
g (1.0 mmol) and 0.15 g of triethylamine
(1.5 mmol) and 0.16 g (1.5 mmol) of N, N-dimethylcarbamoyl chloride were heated to reflux in 20 ml of acetonitrile. The solvent was concentrated under reduced pressure,
The mixture was extracted with ethyl acetate, and the organic layer was washed with water. After drying over anhydrous magnesium sulfate, the residue obtained by evaporating the solvent under reduced pressure was isolated and purified by silica gel column chromatography (hexane: ethyl acetate = 9: 1) to obtain 0.22 g of the desired product (yield 5).
4%). 45-47 ° C

<Production Example 5> 3- {7-Chloro-5-fluoro-2- [1- (propargyloxy) ethyl] benzofuran-4-yl} -1
Preparation of -methyl-6-trifluoromethyl-2 (1H) -pyridone (Compound No. 2-14) 3- [7-chloro-5-fluoro-2- (1-bromoethyl) benzofuran-4-yl] -1 -Methyl-6-trifluoromethyl-2 (1H) -pyridone 0.20 g
(0.44 mmol) in 10 ml of propargyl alcohol
and stirred at 80 ° C. for 2 hours. The solvent was distilled off under reduced pressure, extracted with ethyl acetate, and the organic layer was washed with water. After drying over anhydrous magnesium sulfate, the residue obtained by evaporating the solvent under reduced pressure was isolated and purified by silica gel column chromatography (hexane: ethyl acetate = 5: 1) to obtain the title compound.
17 g (90% yield) were obtained. 61-62 ° C

<Production Example 6> 3- (2-Amino-4,6-difluorobenzothiazol-7-yl) -1-methyl-6-trifluoromethyl-2 (1H) -pyridone (Compound No. 5-1) Preparation of 3- (2,4-difluoro-5) in 20 ml of ethanol
5.4 g (16.1 mmol) of nitrophenyl) -1-methyl-6-trifluoromethyl-2 (1H) -pyridone
l) and 5.7 g (48.3 mmol) of tin powder were suspended, and 15 ml of concentrated hydrochloric acid was added dropwise thereto with stirring at room temperature.
Stirred for hours. After completion of the reaction, excess ethanol was distilled off under reduced pressure. Ethyl acetate and a saturated aqueous solution of sodium hydrogen carbonate were added, and the precipitate was separated by filtration. After drying the organic layer with anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The obtained crude amino compound was dissolved in 50 ml of acetic acid, and 3.1 g (40.7 mmol) of ammonium thiocyanate was added at room temperature, followed by stirring for 2 hours. 3.0 g (18.8) of bromine was added to the reaction solution under ice cooling.
(mmol) in acetic acid and further stirred at room temperature for 8 hours. After the completion of the reaction, the reaction solution was poured into water, and made alkaline by adding aqueous ammonia. The precipitated crystals were collected by filtration, and the obtained crude crystals were washed with ethyl acetate and dried in vacuo. Recrystallization from ethyl acetate and isopropyl ether gave 3.8 g of the desired product (yield 65%). 275-276 ° C

<Production Example 7> 3- (4,6-Difluoro-2-methanesulfonylaminobenzothiazol-7-yl) -1-methyl-6-trifluoromethyl-2 (1H) -pyridone (Compound No. 5) Preparation of -4) 3- (2-amino-4,6-difluorobenzothiazol-7-yl) -1-methyl-6-trifluoromethyl-2 (1H) -pyridone 2.0 g (5.5 mmol) and 0.16 g of methanesulfonyl chloride (11.0 m
mol) was dissolved in ml of methylene chloride, and 1.4 g (13.8 mmol) of triethylamine was added thereto under ice cooling, followed by stirring for 2 hours. The reaction solution was poured into water, extracted with methylene chloride, washed with water, dried over anhydrous magnesium sulfate, and methylene chloride was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 1.7 g (yield 70%) of the desired product. Melting point 200-202
° C

<Production Example 8> 3- [4,6-Difluoro-2- (N-methyl-N-methanesulfonylamino) benzothiazol-7-yl]
-1-methyl-6-trifluoromethyl-2 (1H)-
Preparation of pyridone (Compound No. 5-5) 3- (4,6-difluoro-2-methanesulfonylaminobenzothiazol-7-yl) -1-methyl-6-trifluoromethyl-2 (1H) -pyridone 70g
(1.59 mmol) was dissolved in 5 ml of DMF, and 0.07 g (1.75 mm
ol), and the mixture was stirred at room temperature for 15 minutes, and then 0.34 g (2.39 mmol) of methyl iodide was added. 3 at room temperature
After stirring for an hour, the mixture was poured into water and extracted with ethyl acetate.
After washing with water, the extract is dried over anhydrous magnesium sulfate, and the residue obtained by evaporating ethyl acetate under reduced pressure is purified by silica gel column chromatography to obtain 0.22 g of the desired product (yield 30%). Was. 240-242 ° C

<Production Example 9> 3- (2-Methyl-4-chloro-6-fluorobenzoxazol-7-yl) -1-methyl-6-trifluoromethyl-2 (1H) -pyridone (Compound No. 5) -6)
Preparation of 3- (4-chloro-6-fluoro-2-hydroxyphenyl) -1-methyl-6-trifluoromethyl-2 (1
H) -Pyridone 0.88 g (2.74 mmol) was dissolved in sulfuric acid 20 ml, and fuming nitric acid 0.20 g under ice cooling.
(3.17 mmol) was added dropwise. After stirring for 30 minutes under ice cooling, the mixture was poured into ice water, extracted with ethyl acetate, washed with an aqueous solution of sodium hydrogen carbonate and water, dried over anhydrous magnesium sulfate, and the ethyl acetate was distilled off under reduced pressure. The obtained residue was dissolved in methylene chloride (20 ml), and triethylamine (0.36 g, 3.56 mmol) and acetyl chloride (0.24 g, 3.06 mmol) were added. After stirring at room temperature for 3 hours, the mixture was poured into water and extracted with ethyl acetate. After washing with water, the mixture was dried over anhydrous magnesium sulfate, and the residue obtained by evaporating ethyl acetate under reduced pressure was purified by silica gel column chromatography to give 3- (2-acetoxy-
4-chloro-6-fluoro-3-nitrophenyl) -1
0.61 g (yield 54%) of -methyl-6-trifluoromethyl-2 (1H) -pyridone was obtained. The obtained 3-
0.45 g of (2-acetoxy-4-chloro-6-fluoro-3-nitrophenyl) -1-methyl-6-trifluoromethyl-2 (1H) -pyridone (1.10 mmol)
l) and 0.60 g (5.05 mmol) of powdered tin were suspended in 20 ml of ethanol, and 3 ml of concentrated hydrochloric acid was added dropwise thereto with stirring at room temperature, followed by stirring for 1 hour. After completion of the reaction, excess ethanol was distilled off under reduced pressure, and ethyl acetate and a saturated aqueous solution of sodium hydrogen carbonate were added.
Washed with water and 10% citric acid aqueous solution. The ethyl acetate was dried over anhydrous magnesium sulfate, and the ethyl acetate was distilled off under reduced pressure. The obtained residue was dissolved in acetic acid (20 ml), and the mixture was stirred under heating and reflux for 8 hours. The reaction solution was poured into water and extracted with ethyl acetate. After washing with water and an aqueous solution of sodium hydrogen carbonate, the mixture was dried over anhydrous magnesium sulfate, and the residue obtained by evaporating ethyl acetate under reduced pressure was purified by silica gel column chromatography to obtain 0.22 g of the desired product (yield 55
%). 158-159 ° C

<Production Example 10> 3- (7-Chloro-5-fluoro-2-methyl-2,3
-Dihydrobenzofuran-4-yl) -1-methyl-6
Preparation of -trifluoromethyl-2 (1H) -pyridone (Compound No. 7-1) 3- (4-chloro-2-fluoro-5-allyloxyphenyl) -1-methyl-6-trifluoromethyl-2
0.30 g (0.83 mmol) of (1H) -pyridone and 0.22 g (1.65 mmol) of aluminum chloride were heated and refluxed in 15 ml of methylene chloride for 2 hours. The reaction solution was poured into water, extracted with ethyl acetate, and the organic layer was washed with an aqueous sodium hydrogen carbonate solution. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the residue was subjected to silica gel column chromatography (hexane: ethyl acetate = 5: 1).
And 0.17 g (57% yield) of the desired product was obtained. 146-147 ° C

<Production Example 11> 3- [2,4-Dichloro-5- (1-methoxyethylthio) phenyl] -1-methyl-6-trifluoromethyl-2 (1H) -pyridone (Compound No. 8- Production of 3) 3- (2,4-dichloro-5-mercaptophenyl)-
0.20 g (0.565 mmol) of 1-methyl-6-trifluoromethyl-2 (1H) -pyridone was dissolved in 10 ml of diethyl ether, and 56 mg of dimethyl acetal was dissolved.
(0.622 mmol) and anhydrous magnesium bromide 15
6 mg (0.849 mmol) was added, and the mixture was stirred at room temperature for 2 hours. After removing insolubles by filtration, the mixture was extracted with ethyl acetate, and the organic layer was washed with water. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the residue was subjected to silica gel column chromatography (hexane: ethyl acetate = 3:
The desired product was isolated and purified in 1) to obtain 0.12 g (yield 52%) of the desired product. Melting point 78-79 ° C

<Production Example 12> 3- [4-Chloro-2-fluoro-5- (2-hydroxypropoxy) phenyl] -1-methyl-6-trifluoromethyl-2 (1H) -pyridone (Compound No. 8) -1
Preparation of 0) 3- (4-Chloro-2-fluoro-5-acetonyloxyphenyl) -1-methyl-6-trifluoromethyl-
0.73 g (1.93 mmol) of 2 (1H) -pyridone
Was dissolved in 30 ml of methanol, 79 mg (2.09 mmol) of sodium borohydride was added, and the mixture was stirred at room temperature for 20 minutes. The solvent was distilled off under reduced pressure, extracted with ethyl acetate, and the organic layer was washed with water. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the residue was subjected to silica gel column chromatography (hexane: ethyl acetate = 2:
The product was isolated and purified in 1) to obtain 0.71 g (yield 96%) of the desired product. 85-86 ° C

<Production Example 13> 3- [4-Chloro-2-fluoro-5- (2-methoxypropoxy) phenyl] -1-methyl-6-trifluoromethyl-2 (1H) -pyridone (Compound No. 8) -2
Production of 0) 0.15 g of 3- [4-chloro-2-fluoro-5- (2-hydroxypropoxy) phenyl] -1-methyl-6-trifluoromethyl-2 (1H) -pyridone (0.3
95 mmol) was dissolved in 10 ml of tetrahydrofuran, and 19 mg (0.4%) of sodium hydride (purity: 60%) was dissolved.
After stirring at room temperature for 10 minutes, 67 mg (0.473 mmol) of methyl iodide was added, and the mixture was stirred at room temperature for 1 hour. The mixture was extracted with ethyl acetate, and the organic layer was washed with water. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the residue was isolated and purified by silica gel column chromatography (hexane: ethyl acetate = 3: 1) to give 0.11 g of the desired product (yield 71%). Obtained. Melting point 65-6
6 ℃

<Production Example 14> 3- [7-Chloro-5-fluoro-2- (1-methyl-
1-hydroxyethyl) benzofuran-4-yl] -1
Preparation of -methyl-6-trifluoromethyl-2 (1H) -pyridone (Compound No. 9-16) 7-chloro-5-fluoro-4- (1-methyl-6-trifluoromethyl-2 (1H)- Pyridone-4-yl)
0.80 g of benzofuran-2-carboxylic acid (2.1 mm
ol) was heated to reflux in 20 ml of thionyl chloride for 2 hours. After cooling to room temperature, excess thionyl chloride was distilled off under reduced pressure, and the residue was dissolved in 20 ml of tetrahydrofuran.
Methylmagnesium bromide tetrahydrofuran solution 5.6
ml (5.2 mmol 0.92 mmol / ml) was added dropwise, and the mixture was stirred for 1 hour, and then an aqueous ammonium chloride solution was added to neutralize the reaction system. The solvent was concentrated under reduced pressure and extracted with ethyl acetate, and the organic layer was washed with water. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the residue was subjected to silica gel column chromatography (hexane: ethyl acetate = 2:
By isolation and purification in 1), 0.39 g (yield 47%) of the desired product was obtained. Melting point 64-66 ° C

<Production Example 15> 3- (2,4-Dichloro-6-fluorobenzothiazol-7-yl) -1-methyl-6-trifluoromethyl-2 (1H) -pyridone (Compound No. 5-219) Production of 0.12 g of copper (II) chloride in 10 ml of acetonitrile
(0.89 mmol), 0.3 g of 3- (2-amino-4-chloro-6-fluorobenzothiazol-7-yl) -1-methyl-6-trifluoromethyl-2 (1H) -pyridone (0. 79 mmol) was added. Under salt ice, 0.14 g (1.20 mmol) of isoamyl nitrite was added dropwise, and the mixture was stirred for 30 minutes under salt ice, and further stirred at room temperature for 2 hours. After completion of the reaction, the reaction solution was poured into water and extracted with ethyl acetate. After washing with water, the organic layer was dried with anhydrous magnesium sulfate. After the ethyl acetate was distilled off under reduced pressure, the obtained crude crystals were washed with n-hexane to obtain 0.10 g of the desired product
(Yield 31%) was obtained. 185-186 ° C

<Production Example 16> 3- (4-Chloro-6-fluoro-2-ethoxybenzothiazol-7-yl) -1-methyl-6-trifluoromethyl-2 (1H) -pyridone (Compound No. 5) -22
Production of 0) Ethanol 0.1 ml (2.17 mm) in THF 50 ml
ol), 40 mg of 60% sodium hydride (1.00 m
mol) and stirred at room temperature for 30 minutes.
(2,4-dichloro-6-fluorobenzothiazole-
7-yl) -1-methyl-6-trifluoromethyl-2
0.30 g (0.76 mmol) of (1H) -pyridone was added, and the mixture was further stirred at room temperature for 2 hours. After completion of the reaction, the reaction solution was poured into water, extracted with ethyl acetate, and the organic layer was washed with water. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the residue was isolated and purified by silica gel column chromatography to obtain 0.36 g (yield 99%) of the desired product. 137-138 ° C

<Production Example 17> 3- (4-Chloro-6-fluoro-2-mercaptobenzoxazol-7-yl) -1-methyl-6-trifluoromethyl-2 (1H) -pyridone (Compound No. 5) −
Preparation of 213) 3- (3-amino-4) was added to 30 ml of ethanol and 4 ml of water.
-Chloro-6-fluoro-2-hydroxyphenyl)-
8.0 g (23.8 mmol) of 1-methyl-6-trifluoromethyl-2 (1H) -pyridone and 4.2 g (26.2 mmol) of potassium xanthogenate were suspended, and the mixture was stirred under reflux with heating for 3 hours. After completion of the reaction, the reaction solution was poured into water, adjusted to pH 1 with 1N hydrochloric acid, and extracted with ethyl acetate. After washing with water, the organic layer was dried with anhydrous magnesium sulfate. After the ethyl acetate was distilled off under reduced pressure, the obtained crude crystals were washed with n-hexane to obtain 8.1 g (yield 90%) of the desired product. 270-272 ° C

<Production Example 18> 3- (4-Chloro-6-fluoro-2-methylmercaptobenzoxazol-7-yl) -1-methyl-6
Preparation of trifluoromethyl-2 (1H) -pyridone (Compound No. 5-75) 3- (4-chloro-6-fluoro-2-mercaptobenzoxazol-7-yl) -1-methyl-6-trifluoromethyl 8.1 g of -2 (1H) -pyridone (21.
4 mmol) was dissolved in 50 ml of DMF, and 3.6 g (26.1 mmol) of potassium carbonate and 6.7 g of methyl iodide were dissolved.
(47.5 mmol) was added and stirred at room temperature for 1 hour.
The mixture was extracted with ethyl acetate, and the organic layer was washed with water. After drying over anhydrous magnesium sulfate, the residue obtained by evaporating the solvent under reduced pressure was isolated and purified by silica gel column chromatography to obtain 5.30 g (yield 63%) of the desired product. Melting point 162-1
63 ° C

<Production Example 19> 3- (4-Chloro-6-fluoro-2-methylsulfonylbenzoxazol-7-yl) -1-methyl-6
Preparation of trifluoromethyl-2 (1H) -pyridone (Compound No. 5-214) 3- (4-Chloro-6-fluoro-2-methylmercaptobenzoxazol-7-yl) -1-methyl-6
Trifluoromethyl-2 (1H) -pyridone 5.0 g
(12.8 mmol) was dissolved in 30 ml of chloroform, and m-chloroperbenzoic acid (purity 80%) was added under ice cooling.
6.0 g (27.9 mmol) were added. After stirring at room temperature for 3 hours, the mixture was poured into water and extracted with chloroform. After washing with an aqueous solution of sodium hydrogen carbonate, an aqueous solution of sodium hydrogen sulfite and water, drying with anhydrous magnesium sulfate, chloroform was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography to obtain the desired product. 22
g (yield 59%) was obtained. Melting point 253-255 ° C

<Production Example 20> 3- (2-Methylamino-4-chloro-6-fluorobenzoxazol-7-yl) -1-methyl-6-trifluoromethyl-2 (1H) -pyridone (Compound No. 5
Production of -215) 1.8 g of 3- (4-chloro-6-fluoro-2-methylsulfonylbenzoxazol-7-yl) -1-methyl-6-trifluoromethyl-2 (1H) -pyridone in a sealed pressure tube. (4.2 mmol), 10 ml of a 2N methylamine / tetrahydrofuran solution was added, and the mixture was stirred at 150 ° C. for 4 hours while heating. After completion of the reaction, the solvent was distilled off under reduced pressure, extracted with ethyl acetate, and the organic layer was washed with a 10% aqueous citric acid solution and water. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 1.20 g (yield: 75%) of the desired product. 214-216 ° C

<Production Example 21> 3- (2-Amino-4-chloro-6-fluoro-3-methoxyphenyl) -1-methyl-6-trifluoromethyl-2 (1H) -pyridone (Compound No. 8- 225) Production of fuming nitric acid 4.0 g in acetic anhydride 30 ml under salt ice cooling
(63.5 mmol) was added dropwise. After stirring for 30 minutes under ice-cooling, 6.0 g (17.9 mmol) of 3- (4-chloro-6-fluoro-3-methoxyphenyl) -1-methyl-6-trifluoromethyl-2 (1H) -pyridone was obtained. )
Was added and the mixture was stirred under ice cooling for 2 hours. After completion of the reaction, the reaction solution was poured into ice water, extracted with ethyl acetate, washed with an aqueous solution of sodium hydrogen carbonate and water, dried over anhydrous magnesium sulfate, and the ethyl acetate was distilled off under reduced pressure. The obtained residue and 6.5 g (55.1 mmol) of tin powder were suspended in 100 ml of ethanol, and 10 ml of concentrated hydrochloric acid was added dropwise to the reaction solution under stirring at room temperature, followed by stirring for 1 hour. After completion of the reaction, excess ethanol was distilled off under reduced pressure, and ethyl acetate and a saturated aqueous solution of sodium hydrogen carbonate were added.
Washed with water and 10% citric acid aqueous solution. After drying the organic layer with anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 3.56 g (yield 56%) of the desired product. Melting point 18
8-189 ° C

<Production Example 22> 3- (2-Amino-4-chloro-6-fluoro-3-hydroxyphenyl) -1-methyl-6-trifluoromethyl-2 (1H) -pyridone (Compound No. 8- 233)
Preparation of 3- (2-amino-4-chloro-6-fluoro-3-methoxyphenyl) -1-methyl-6-trifluoromethyl-2 (1H) -pyridone 3.1 g (8.86 mmol)
l) in 50 ml of methylene chloride and dry ice
Under cooling in an acetone bath, 36 ml (18.0 mmol) of a 2N boron tribromide methylene chloride solution was added dropwise, and the mixture was stirred at room temperature for 4 hours. After completion of the reaction, the reaction mixture was poured into ice water, extracted with methylene chloride, washed with an aqueous solution of sodium hydrogen carbonate and water, dried over anhydrous magnesium sulfate, and methylene chloride was distilled off under reduced pressure. The obtained crude crystals were washed with n-hexane to obtain 2.5 g (yield 84%) of a target product. Melting point 186-18
7 ℃

<Production Example 23> 3- (7-Chloro-5-fluoro-2-hydroxybenzoxazol-4-yl) -1-methyl-6-trifluoromethyl-2 (1H) -pyridone (Compound No. 5) −
66) Preparation of 3- (2-amino-4-chloro-6-fluoro-3-hydroxyphenyl) -1-methyl-6-trifluoromethyl-2 (1H) -pyridone 0.25 g (0.71 mm)
ol), carbonyldiimidazole (CDI) 0.18
g (1.11 mmol) in 10 ml of DMF and 9
The mixture was heated and stirred at 0 ° C. for 1 hour. After the reaction, drain into water,
Extracted with ethyl acetate. After washing with water, the organic layer was dried over anhydrous magnesium sulfate, and ethyl acetate was distilled off under reduced pressure. The obtained crude crystals were washed with n-hexane to obtain 0.26 g (yield 98%) of the target product. Melting point 175-178
° C

<Production Example 24> 3- (7-Chloro-5-fluoro-2-mercaptobenzoxazol-4-yl) -1-methyl-6-trifluoromethyl-2 (1H) -pyridone (Compound No. 4) −
83) Production of 3- (2-amino-4) in 30 ml of ethanol and 4 ml of water.
-Chloro-6-fluoro-3-hydroxyphenyl)-
0.5 g (1.42 mmol) of 1-methyl-6-trifluoromethyl-2 (1H) -pyridone and 0.3 g (1.87 mmol) of potassium xanthate were suspended and stirred for 3 hours under reflux with heating. After completion of the reaction, the reaction solution was poured into water, adjusted to pH 1 with 1N hydrochloric acid, and extracted with ethyl acetate. After washing with water, the organic layer was dried with anhydrous magnesium sulfate. After the ethyl acetate was distilled off under reduced pressure, the obtained crude crystals were washed with n-hexane. 0.52 g (yield 97%) of the desired product was obtained. ¹ H-NMR (300 MHz, CDCl ₃ ) δ value: 3.
74 (3H, d), 6.81 (1H, d), 7.04
(1H, d), 7.60 (1H, d), 12.58 (1
H, s) ppm

<Production Example 25> 3- (7-Chloro-2-ethylmercapto-5-fluorobenzoxazol-4-yl) -1-methyl-6
Preparation of trifluoromethyl-2 (1H) -pyridone (Compound No. 4-76) 3- (7-Chloro-5-fluoro-2-mercaptobenzoxazol-4-yl) -1-methyl-6-trifluoromethyl 0.26 g of -2 (1H) -pyridone (0.
68 mmol) in 10 ml of DMF, and 0.14 g (0.1 mmol) of potassium carbonate, 0.1 ml of ethyl iodide.
4 g (0.915 mmol) was added, and the mixture was stirred at room temperature for 1 hour. The mixture was extracted with ethyl acetate, and the organic layer was washed with water. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the residue was isolated and purified by silica gel column chromatography to obtain 0.26 g (yield 93%) of the desired product. Melting point 12
7 to 128 ° C

<Production Example 26> 3- (4-Chloro-2-fluoro-5-diethoxyphosphorylmethylphenyl) -1-methyl-6-trifluoromethyl-2 (1H) -pyridone (Compound No. 1-4)
Preparation of 2) 3- (4-chloro-2-fluoro-5-bromomethylphenyl) -1-methyl-6-trifluoromethyl-2
(1H) -pyridone 0.18 g (0.45 mmol),
0.18 g (1.08 mmol) of triethyl phosphite was dissolved in 20 ml of toluene and stirred for 4 hours under reflux with heating. . After completion of the reaction, toluene was added, and the mixture was washed with water. The organic layer was dried over anhydrous magnesium sulfate, and toluene was distilled off under reduced pressure. The obtained residue was isolated and purified by silica gel column chromatography to give 0.20 g of the desired product (yield 97
%). ¹ H-NMR (400 MHz, CDCl ₃ ) δ value: 1.
29 (6H, t), 3.36 (2H, d), 3.67
(3H, s), 4.06 (4H, q), 6.75 (1
H, d), 7.22 (1H, d), 7.48 (1H,
d), 7.61 (1H, d) ppm

<Production Example 27> 3- (5-amino-4-bromo-2-fluorophenyl) -1-methyl-6-trifluoromethyl-2 (1
Preparation of H) -pyridone (Compound No. 8-180) 3- (4-bromo-2-fluoro-5-nitrophenyl) -1-methyl-6-trifluoromethyl-2 (1
3.95 g (10.00 mmol) of H) -pyridone was dissolved in 30 ml of ethyl acetate, and 10 ml of water, 1 ml of acetic acid and 5.60 g (100.00 mmol) of iron powder were added.
The mixture was heated and stirred at 50 ° C. for a time. After removing insolubles by filtration, the mixture was extracted with ethyl acetate, and the organic layer was washed with water. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to obtain 3.65 g (yield 100%) of the desired product.

¹ H-NMR (300 MHz, CDC
l ₃ ) δ value: 3.68 (3H, s), 3.98 (2H,
br), 6.74 (1H, d), 6.97 (1H,
d), 7.23 (1H, s), 7.47 (1H, d) p
pm

<Production Example 28> 3- (5-amino-4-cyano-2-fluorophenyl) -1-methyl-6-trifluoromethyl-2 (1
Preparation of H) -pyridone (Compound No. 8-210) 3- (5-amino-4-bromo-2-fluorophenyl) -1-methyl-6-trifluoromethyl-2 (1
H) -Pyridone 3.65 g (10.00 mmol) in D
Dissolve in 10 ml of MF, and add 0.88 g of zinc cyanide (7.
50 mmol) and 1.16 g (1.00 mmol) of tetrakistriphenylphosphine palladium.
Heated to reflux for an hour. The reaction solution was poured into water and extracted with ethyl acetate, and the organic layer was washed with water. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to obtain 1.95 of the target compound.
g (62.7% yield). Melting point: 240-243 ° C

<Production Example 29> 3- (4-bromo-2-fluoro-5-methylaminophenyl) -1-methyl-6-trifluoromethyl-2
Production of (1H) -pyridone (Compound No. 8-220) 3- (5-amino-4-bromo-2-fluorophenyl) -1-methyl-6-trifluoromethyl-2 (1
H) -Pyridone 7.30 g (20.00 mmol) in D
Dissolved in 30 ml of MF, 0.80 g (20.00 mmol) of 60% sodium hydride was added thereto at 0 ° C.
Stirred for hours. Further there 3.55 g of methyl iodide
(20.00 mmol), and the mixture was heated and stirred at 50 ° C. for 2 hours. The reaction solution was poured into water and extracted with ethyl acetate, and the organic layer was washed with water. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain the desired product.
50 g (59.4%) were obtained. Melting point: 156-157 ° C

<Production Example 30> 3- (4-cyano-2-fluoro-5-methylaminophenyl) -1-methyl-6-trifluoromethyl-2
Preparation of (1H) -pyridone (Compound No. 8-221) 3- (4-bromo-2-fluoro-5-methylaminophenyl) -1-methyl-6-trifluoromethyl-2
4.50 g (11.90 mmol) of (1H) -pyridone
Was dissolved in 20 ml of DMF, and 0.84 g of zinc cyanide was dissolved.
(7.12 mmol) and 1.37 g (1.19 mmol) of tetrakistriphenylphosphine palladium were added, and the mixture was heated under reflux for 5 hours. The reaction solution was poured into water and extracted with ethyl acetate, and the organic layer was washed with water. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 2.70 g (69.8%) of the desired product. Melting point: 2
20-222 ° C

<Production Example 31> 3- (4-cyano-2-fluoro-5-N-methyl-N
Preparation of -propargylaminophenyl) -1-methyl-6-trifluoromethyl-2 (1H) -pyridone (Compound No. 8-223) 3- (4-cyano-2-fluoro-5-methylaminophenyl) -1 -Methyl-6-trifluoromethyl-2
1.00 g (3.00 mmol) of (1H) -pyridone was dissolved in 10 ml of DMF, and 0.22 g (3.60 mmol) of 60% sodium hydride was added thereto at 0 ° C.
Stirred for hours. Furthermore, propargyl bromide was added.
43 g (3.60 mmol) was added, and the mixture was heated and stirred at 120 ° C. for 1 hour. The reaction solution was poured into water and extracted with ethyl acetate, and the organic layer was washed with water. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 0.06 g (5.70%) of the desired product. Melting point: 115-1
16 ° C

<Production Example 32> 3- (4-Bromo-2-chloro-5-hydroxyphenyl) -1-methyl-6-trifluoromethyl-2 (1
Preparation of H) -pyridone (Compound No. 8-212) 3- (4-bromo-2-chloro-5-methoxyphenyl) -1-methyl-6-trifluoromethyl-2 (1
11.9 g (30.00 mmol) of H) -pyridone was dissolved in 100 ml of methylene chloride, and 45.0 ml of a 2N boron tribromide methylene chloride solution was added dropwise while cooling to -60 ° C. After stirring at room temperature overnight, the reaction solution was poured into water and extracted with ethyl acetate. After washing with water, the mixture was dried over anhydrous magnesium sulfate, and the organic layer was distilled off under reduced pressure to obtain the desired product 1.
1.5 g (100% yield) were obtained. Melting point: 222-22
4 ℃

<Production Example 33> 3- (4-Bromo-2-chloro-5-n-propoxyphenyl) -1-methyl-6-trifluoromethyl-2
Production of (1H) -pyridone (Compound No. 8-213) 3- (4-bromo-2-chloro-5-hydroxyphenyl) -1-methyl-6-trifluoromethyl-2 (1
H) -Pyridone 1.15 g (3.00 mmol) in TH
F4 in 20 ml and triphenylphosphine 0.94
g (3.60 mmol) and n-propanol 0.22
g (3.6 mmol), and 0.68 g (3.60 m) of a 40% dimethyl azodicarboxylate solution at room temperature.
mol) was added dropwise. After stirring at room temperature overnight, the reaction solution was poured into water and extracted with ethyl acetate. After washing with water,
The organic layer was dried over anhydrous magnesium sulfate. After evaporating the ethyl acetate under reduced pressure, the obtained residue was purified by silica gel column chromatography to obtain 1.27 g of the desired product
(100% yield). Melting point: 89-91 ° C

<Production Example 34> 3- (4-cyano-2-chloro-5-n-propoxyphenyl) -1-methyl-6-trifluoromethyl-2
Preparation of (1H) -pyridone (Compound No. 8-215) 3- (4-bromo-2-chloro-5-n-propoxyphenyl) -1-methyl-6-trifluoromethyl-2
1.27 g (3.00 mmol) of (1H) -pyridone was dissolved in 10 ml of DMI, and 0.32 g of copper cyanide (3.
60 mmol) and 0.05 g of potassium iodide (0.3 g).
0 mmol), and the mixture was heated and stirred at 150 ° C. for 6 hours. The reaction solution was poured into water and extracted with ethyl acetate, and the organic layer was washed with water. After drying over anhydrous magnesium sulfate,
After evaporating the solvent under reduced pressure, the obtained residue was purified by silica gel column chromatography to obtain 0.50 g of the desired product
(45.0%). Melting point: 95-96 ° C

<Production Example 35> 3- (4-cyano-2-fluoro-5-methoxyphenyl) -1-methyl-6-trifluoromethyl-2 (1
Preparation of H) -pyridone (Compound No. 8-177) 3- (4-bromo-2-fluoro-5-methoxyphenyl) -1-methyl-6-trifluoromethyl-2 (1
H) -Pyridone 2.38 g (6.00 mmol) in DM
I dissolved in 10 ml and copper cyanide 0.65 g (7.20
mmol) and 0.10 g of potassium iodide (0.60 m
mol), and the mixture was heated and stirred at 150 ° C. for 20 hours.
The reaction solution was poured into water, extracted with ethyl acetate, and the organic layer was washed with water. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 1.20 g of the desired product
(58.3%). Melting point: 181-182 ° C

<Production Example 36> 3- (4-cyano-2-fluoro-5-hydroxyphenyl) -1-methyl-6-trifluoromethyl-2 (1
Production of H) -pyridone (Compound No. 8-192) 3- (4-cyano-2-fluoro-5-methoxyphenyl) -1-methyl-6-trifluoromethyl-2 (1
1.20 g (3.50 mmol) of H) -pyridone was dissolved in 20 ml of methylene chloride, and 10.0 ml of a 2N boron tribromide methylene chloride solution was added dropwise at room temperature. After stirring under reflux for 3 hours, the reaction solution was poured into ice water and extracted with chloroform. After washing with water, the mixture was dried over anhydrous magnesium sulfate, and the organic layer was distilled off under reduced pressure to obtain 1.00 g of the desired product (yield: 87.0%). Melting point: 225-227 ° C

<Production Example 37> 3- (4-cyano-2-chloro-5-propargyloxyphenyl) -1-methyl-6-trifluoromethyl-
Preparation of 2 (1H) -pyridone (Compound No. 8-219) 3- (4-cyano-2-chloro-5-
1.00 g of (hydroxyphenyl) -1-methyl-6-trifluoromethyl-2 (1H) -pyridone (3.04 m
mol), 0.50 g (3.65 mmol) of potassium carbonate
l) and 0.54 g (4.56 m) of propargyl bromide
mol), and the mixture was stirred at 80 ° C for 1 hour. The reaction solution was poured into water and extracted with ethyl acetate. After washing with water, the organic layer was dried with anhydrous magnesium sulfate. After the ethyl acetate was distilled off under reduced pressure, the obtained residue was purified by silica gel column chromatography to obtain 0.32 g (yield: 28.8%) of the desired product. Melting point: 165-167 ° C

<Production Example 38> 3- (4-cyano-2,5-difluorophenyl) -1
Preparation of -methyl-6-trifluoromethyl-2 (1H) -pyridone (Compound No. 8-230) 3- (4-bromo-2,5-difluorophenyl) -1
9.20 g (25.00 mmol) of -methyl-6-trifluoromethyl-2 (1H) -pyridone was treated with DMI 50m.
and dissolved in 2.70 g (30.00 mmol) of copper cyanide.
l) and 0.42 g of potassium iodide (2.50 mmol
l) was added and the mixture was heated and stirred at 150 ° C. for 8 hours. The reaction solution was poured into water, extracted with ethyl acetate, and the organic layer was washed with water. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 4.80 g of the desired product (61.
1%). Melting point: 129-131 ° C

<Production Example 39> 3- (4-cyano-2-fluoro-5-n-propylaminophenyl) -1-methyl-6-trifluoromethyl-2 (1H) -pyridone (Compound No. 8-234) Preparation of 3- (4-cyano-2,5-difluorophenyl) -1-methyl-6-trifluoromethyl-2 (1
H) -Pyridone 0.62 g (2.00 mmol), DM
SO 10 ml, n-propylamine 0.60 g (10.
00 mmol), and the mixture was heated and stirred at 120 ° C. for 6 hours. The reaction solution was poured into water, extracted with ethyl acetate,
The organic layer was washed with water. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain the desired product 0.1
2 g (16.9%) were obtained. Melting point: 131-133 ° C

Examples of the compounds of the present invention produced according to the methods shown in Production Examples 1 to 39 are shown in Tables 57 to 59 together with the compounds shown in the above Production Examples.

[0225]

[Table 57]

[0226]

[Table 58]

[0227]

[Table 59]

[0228] Next, some of the compounds of the invention ¹
The H-NMR data is shown in Tables 60 and 61.

[0229]

[Table 60]

[0230]

[Table 61]

Next, the production examples of useful intermediates for producing the compound of the present invention are shown below with reference. Intermediate Production Example 1 Production of 4-chloro-2-fluoro-5-isopropoxybenzyl bromide 124 g (0.56 mol) of 4-chloro-2-fluoro-5-isopropoxybenzyl alcohol was dissolved in 900 ml of diethyl ether. 55 g of phosphorus bromide (0.2 g
0 mol) was added dropwise thereto under ice cooling. After stirring at room temperature for 3 hours, the mixture was poured into ice water and extracted with diethyl ether.
After washing with water and an aqueous sodium hydrogen carbonate solution, the organic layer was dried over anhydrous magnesium sulfate. Diethyl ether was distilled off under reduced pressure to obtain 143 g of the desired product (89% yield).

Intermediate Production Example 2 Production of 4-chloro-2-fluoro-5-isopropoxyphenylacetonitrile 26 g (0.53 mol) of sodium cyanide was added to DMF.
Dissolved in 700 ml, 4-chloro-2-fluoro-5-
143 g of isopropoxybenzyl bromide (0.50 m
ol) was added dropwise thereto at room temperature. After stirring at room temperature for 8 hours, the mixture was poured into water and extracted with ethyl acetate. After washing with water, the organic layer was dried with anhydrous magnesium sulfate. Ethyl acetate was distilled off under reduced pressure to obtain 107 g of the desired product (yield 92%).

Intermediate Production Example 3 Production of 4-chloro-2-fluoro-5-isopropoxyphenylacetic acid 107 g (0.47 mol) of 4-chloro-2-fluoro-5-isopropoxyphenylacetonitrile was dissolved in 400 ml of ethanol. , Potassium hydroxide 100g
(1.78 mol) and refluxed for 1 hour. After the ethanol was distilled off under reduced pressure, the obtained residue was poured into water, washed with diethyl ether, made acidic with citric acid, and extracted with ethyl acetate. After washing with water, the organic layer was dried with anhydrous magnesium sulfate. After the ethyl acetate was distilled off under reduced pressure, the obtained crude crystals were washed with diisopropyl ether to obtain 70 g of the desired product (yield 61%). Melting point 75
７６76 ° C. ¹ H-NMR (300 MHz, CDCl ₃ ) δ value: 1.
35 (6H, d), 3.66 (2H, s), 4.45
(1H, m), 6.84 (1H, d), 7.16 (1
H, d) ppm

Intermediate Production Example 4 Preparation of ethyl 4-chloro-2-fluoro-5-isopropoxyphenylacetoacetate 47 g (0.19 mol) of 4-chloro-2-fluoro-5-isopropoxyphenylacetic acid was dissolved in 300 ml of THF. 34 g of carbonyldiimidazole (CDI)
(0.21 mol), and the mixture was stirred at room temperature for 3 hours. To this reaction solution was added 50 g of monoethyl potassium malonate (0.2 g).
9 mol) and 28 g of anhydrous magnesium chloride (0.29
mol)) and stirred at 60 ° C for 3 hours. After THF was distilled off under reduced pressure, the obtained residue was poured into water, adjusted to pH 1 with 1N hydrochloric acid, and extracted with ethyl acetate. After washing with water and an aqueous sodium hydrogen carbonate solution, the organic layer was dried over anhydrous magnesium sulfate. After the ethyl acetate was distilled off under reduced pressure, the obtained crude crystals were washed with n-hexane to obtain the desired compound 3
5 g (58% yield) was obtained. Melting point 57-58 ° C ¹ H-NMR (300 MHz, CDCl ₃ ) δ value: 1.
28 (3H, t), 1.35 (6H, d), 3.51
(2H, s), 3.82 (2H, s), 4.19 (2
H, t), 4.47 (1H, m), 6.77 (1H,
d), 7.12 (1H, d) ppm

Intermediate Production Example 5 Production of 3- (2,4-difluorophenyl) -6-trifluoromethyl-2H-pyran-2-one 7.7 g of potassium tert-butoxide (69 mmol)
l) was dissolved in 200 ml of THF, and 10 g (65 mmol) of 2,4-difluorophenylacetonitrile was cooled under ice-cooling.
Was added dropwise. After 10 minutes, (E) -4-ethoxy-1,
1,1-trifluoro-3-buten-2-one 13.5
g (69 mmol) was added dropwise, followed by stirring at room temperature for 4 hours. After THF was distilled off under reduced pressure, the obtained residue was poured into water, adjusted to pH 1 with 1N hydrochloric acid, and extracted with ethyl acetate. After washing with water and an aqueous sodium hydrogen carbonate solution, the organic layer was dried over anhydrous magnesium sulfate, and then ethyl acetate was distilled off under reduced pressure. 150 ml of concentrated hydrochloric acid is added to the obtained residue.
Was added and the mixture was stirred for 4 hours while heating under reflux. The reaction solution was poured into ice water, extracted with ethyl acetate, and washed with water. After the organic layer was dried over anhydrous magnesium sulfate, ethyl acetate was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 13.8 g (yield: 76%) of the desired product. Melting point 98-100 ° C ¹ H-NMR (400 MHz, CDCl ₃ ) δ value: 6.
78 (1H, d), 6.95 (2H, m), 7.52
(1H, d), 7.56 (1H, q) ppm

Intermediate Production Example 6 3- (2,4-difluorophenyl) -1-methyl-6
Preparation of -trifluoromethyl-2 (1H) -pyridone 3- (2,4-difluorophenyl) -6-trifluoromethyl-2H-pyran-2-one 13.8 g (50 m
mol) was dissolved in 150 ml of ethanol, 5.5 g (70 mmol) of a 40% methylamine methanol solution was added, and the mixture was stirred under heating and reflux for 6 hours. The mixture was poured into ice water, extracted with ethyl acetate, washed with 1N hydrochloric acid and water, and the organic layer was dried over anhydrous magnesium sulfate. After evaporating the ethyl acetate under reduced pressure, the obtained residue was purified by silica gel column chromatography to obtain 3.8 g of the desired product (yield 26%). Melting point 123-124 ° C ¹ H-NMR (400 MHz, CDCl ₃ ) δ value: 3.
70 (3H, s), 6.75 (1H, d), 6.90
(2H, m), 7.43 (1H, d), 7.58 (1
H, m) ppm

Intermediate Production Example 7 Production of ethyl 4-chloro-2-fluorophenylacetate 18 g of 4-chloro-2-fluorophenylacetic acid (96 m
mol) and 2.3 g of sulfuric acid were added to 300 ml of ethanol and refluxed for 4 hours. After cooling, ethanol was distilled off, ethyl acetate was added, and the mixture was washed with water and a saturated aqueous solution of sodium hydrogen carbonate. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off, and the crude crystals were washed with n-hexane to obtain the desired product 1
9 g (88 mmol) were obtained. 53-54 ° C

Intermediate Preparation Example 8 Preparation of 3- (4-chloro-2-fluorophenyl) -6-trifluoromethyl-2H-pyran-2-one Ethyl 4-chloro-2-fluorophenylacetate dissolved in 40 ml of THF 19 g (88 mmol) were taken from -65 to
LDA-THF solution cooled to −60 ° C. [1.6 N-n
-Butyl lithium 83 ml (133 mmol), diisopropylamine 15.2 g (150 mmol) and TH
Adjusted from 200ml of F. And stirred for 1 hour. Next, 4-ethoxy-1,1,1-trifluoro-3
After dropping 30 g (180 mmol) of -buten-2-one, cooling was stopped and the mixture was stirred at room temperature for 1 hour. Most TH
After distilling off F, 1N hydrochloric acid was added and extracted with ethyl acetate.
Washed with water. After the solvent was distilled off, 300 ml of concentrated hydrochloric acid was added, and the mixture was refluxed for 4 hours. After cooling, water was added, extracted with ethyl acetate, and washed with water and a saturated aqueous solution of sodium hydrogen carbonate.
After the organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off, and the obtained residue was purified by silica gel column chromatography to obtain 16 g (55 mmol) of the desired product. Melting point 1
07-108 ° C

Intermediate Production Example 9 Production of 3- (4-chloro-2-fluorophenyl) -1-methyl-6-trifluoromethyl-2 (1H) -pyridone 3- (4-chloro-2-fluorophenyl) ) -6-trifluoromethyl-2H-pyran-2-one 9.3 g (3
2 mmol) to 160 ml of methanol, and
3.8 g of a 0% methylamine / methanol solution (48 mm
ol) and the mixture was stirred for 2 hours under ice cooling. A 10% aqueous citric acid solution was added to the reaction solution to make it acidic, followed by extraction with ethyl acetate and washing with water. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off. The obtained residue was dissolved in 160 ml of toluene, 0.4 g (2.1 mmol) of paratoluenesulfonic acid was added, and the mixture was refluxed for 4 hours. After cooling and washing with water, the organic layer was dried over anhydrous magnesium sulfate and the solvent was distilled off. The obtained residue was purified by silica gel chromatography to obtain 5.7 g of the desired product (19 m
mol). 103-104 ° C

Intermediate Production Example 10 Production of α- (2,4-dichlorophenyl) -α-hydroxymethyleneacetonitrile 6.0 g of metallic sodium was added to anhydrous ethanol to prepare an ethanol solution of sodium ethoxide.
While heating to 0 ° C., a mixed solution of 37.2 g of 2,4-dichlorophenylacetonitrile and 22.2 g of ethyl formate was added. After the addition, the mixture was heated and refluxed for another 2 hours, and then left overnight. The reaction solution was cooled to 0 ° C., filtered, washed with diethyl ether, and the collected sodium salt was added to 130
9 ml of acetic acid was added dropwise to 0 ml of distilled water while cooling at 0 ° C. After stirring at room temperature for about 30 minutes after the dropwise addition, the deposited precipitate was collected by filtration and washed with water. This is dried and the desired product 3
1.7 g (74% yield) was obtained. Melting point 162-163 ° C

Intermediate Production Example 11 3- (2,4-dichlorophenyl) -6-methyl-2
Production of (1H) -pyridone α- (2,4-dichlorophenyl) -α-hydroxymethyleneacetonitrile and 8.8 g of acetone were thoroughly mixed with 110 g of polyphosphoric acid, and heated to about 130 ° C. An exothermic reaction started at this temperature. 1 with heating if necessary
Hold at 30-140 ° C. for 30 minutes. The cooled mixture was poured into ice water and the suspension was stirred for 18 hours. The crude was stirred with ethyl acetate and excess dilute aqueous potassium hydroxide to make it alkaline. The deposited precipitate is collected by filtration,
Washing with water, ethyl acetate and diethyl ether sequentially gave 8.0 g (yield 45%) of the desired product. Melting point 266-268
° C

Intermediate Preparation Example 12 Preparation of 3- (2,4-dichlorophenyl) -1-difluoromethyl-6-methyl-2 (1H) -pyridone 3- (2,4-dichlorophenyl) -6-methyl-2
4.0 g of (1H) -pyridone, 0.8 g of tetrabutylammonium bromide and 2.6 g of potassium hydroxide in THF
After dissolving in 100 ml, chlorodifluoromethane was blown under cooling at 0 ° C. After completion of the blowing, stirring was further continued at room temperature for 1 hour to complete the reaction. Next, the solvent was distilled off under reduced pressure, extracted with ethyl acetate, washed with water, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off, and the obtained crude product was purified by silica gel column chromatography to obtain 0.70 g (yield 14%) of the desired product. Melting point 83 ~
85 ° C

Intermediate Production Example 13 1-Amino-3- (2,4-dichlorophenyl) -6
Production of trifluoromethyl-2 (1H) -pyridone To 0.10 g of 60% sodium hydride was added 10 ml of DMF, and 3- (2,4-dichlorophenyl) -6-6- was added under ice cooling.
0.72 g of trifluoromethyl-2 (1H) -pyridone
And further stirred at room temperature for 30 minutes.
0.47 g of 4-dinitrophenoxyamine was added. Next, the mixture was stirred at 50 ° C. for 1 hour to complete the reaction. After completion of the reaction, the reaction solution was washed with water and extracted with ethyl acetate. After drying the organic layer over anhydrous magnesium sulfate, the solvent was distilled off to obtain a crude product. The crude product was purified by silica gel column chromatography to obtain 0.50 g (yield: 68%) of the desired product. Melting point 98-100 ° C

Intermediate Production Example 14 3- (4-Chloro-2-fluoro-5-hydroxyphenyl) -1,5-dimethyl-6-trifluoromethyl-
Preparation of 2 (1H) -pyridone 1.3 g of 3- (4-chloro-2-fluoro-5-isopropoxyphenyl) -1,5-dimethyl-6-trifluoromethyl-2 (1H) -pyridone (10. 4mmo
l) was dissolved in 20 ml of methylene chloride, and cooled to -60 ° C.
1 was added dropwise. After stirring at room temperature for 3 hours, the reaction solution was poured into water and extracted with ethyl acetate. After washing with water and drying over anhydrous magnesium sulfate, the organic layer was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 0.8 g of the desired product (yield 69%). Obtained.
207-208 ° C

Intermediate Production Example 15 Production of 3- (4-chloro-2-fluoro-5-propargyloxyphenyl) -1,5-dimethyl-6-trifluoromethyl-2 (1H) -pyridone 3-D was added to 10 ml of DMF. (4-chloro-2-fluoro-5
-Hydroxyphenyl) -1,5-dimethyl-6-trifluoromethyl-2 (1H) -pyridone 0.20 g
(0.6 mmol), 0.1 g of potassium carbonate (0.7 m
mol) and 0.1 g of propargyl bromide (0.8 m
mol), and the mixture was stirred at 60 ° C for 2 hours. The reaction solution was poured into water and extracted with ethyl acetate. After washing with water, the organic layer was dried with anhydrous magnesium sulfate. After the ethyl acetate was distilled off under reduced pressure, the obtained residue was purified by silica gel column chromatography to obtain 0.12 g (yield 53%) of the desired product. Melting point 107-108 ° C

Intermediate Production Example 16 3- (5-amino-4-chloro-2-fluorophenyl) -1-methyl-6-trifluoromethyl-2 (1
Preparation of H) -pyridone 3- (4-chloro-2-fluoro-5-nitrophenyl) -1-methyl-6-trifluoromethyl-2 (1
H) -Pyridone 1.0 g (2.8 mmol), tin 1.
3 g (11 mmol) was suspended in 30 ml of ethanol, 5 ml of concentrated hydrochloric acid was added at room temperature, and the mixture was stirred for 1 hour. After completion of the reaction, the reaction solution was poured into water to neutralize the reaction solution, and the insolubles were filtered off, and the filtrate was extracted with ethyl acetate. After washing with water and a saturated aqueous solution of sodium hydrogencarbonate, the organic layer was dried over anhydrous magnesium sulfate. After the ethyl acetate was distilled off under reduced pressure,
The obtained crude crystals were washed with diisopropyl ether to obtain 0.90 g (yield 98%) of the desired product. Melting point 155-1
57 ° C

Intermediate Production Example 17 3- (4-Chloro-5-chlorosulfonyl-2-fluorophenyl) -1-methyl-6-trifluoromethyl-
Production of 2 (1H) -pyridone 3- (4-chloro-2-fluorophenyl) -1-methyl-6-trifluoromethyl-2 (1H) -pyridone 2.9 g (9.5 mmol) was added to chlorosulfonic acid 70 g.
And heated and stirred at 100 ° C. for 5 hours. After cooling, the mixture was added dropwise to ice water little by little, extracted with ethyl acetate, washed with water and a saturated aqueous solution of sodium hydrogen carbonate, and the organic layer was dried over anhydrous magnesium sulfate. After the ethyl acetate was distilled off under reduced pressure, the obtained crude crystals were washed with n-hexane to obtain 3.3 g of the desired product (yield 86%). 77-78 ° C

Intermediate Production Example 18 3- (5-acetylthio-4-chloro-2-fluorophenyl) -1-methyl-6-trifluoromethyl-2
Production of (1H) -pyridone 3.1 g of 3- (4-chloro-5-chlorosulfonyl-2-fluorophenyl) -1-methyl-6-trifluoromethyl-2 (1H) -pyridone in 50 ml of acetic acid (7. 7
mmol), 1.2 g (38 mmol) of red phosphorus and 0.12 g (0.47 mmol) of iodine, and the mixture was heated under reflux for 1 hour. After cooling, insolubles were filtered and most of the acetic acid was distilled off. The resulting residue was poured into water and extracted with ethyl acetate. After washing with water and a saturated aqueous solution of sodium hydrogencarbonate, the organic layer was dried over anhydrous magnesium sulfate. After the ethyl acetate was distilled off under reduced pressure, the obtained residue was purified by silica gel column chromatography to obtain 2.8 g of the desired product (yield 9).
8%). Melting point 91-92 ° C

Intermediate Production Example 19 3- (4-Chloro-2-fluoro-5-mercaptophenyl) -1-methyl-6-trifluoromethyl-2 (1
Preparation of H) -pyridone 3- (5-acetylthio-4-chloro-2-fluorophenyl) -1-methyl-6-trifluoromethyl-2
2.8 g (7.7 mmol) of (1H) -pyridone was dissolved in 30 ml of methanol, and 8.5 ml (8.5 mmol) of a 1 N aqueous sodium hydroxide solution was added dropwise under ice cooling. After stirring at room temperature for 1 hour, the mixture was poured into water, acidified with citric acid, and extracted with ethyl acetate. After washing with water and saturated saline, the organic layer was dried over anhydrous magnesium sulfate. After the ethyl acetate was distilled off under reduced pressure, the obtained crude crystals were washed with n-hexane to obtain 2.4 g of the desired product (yield 93%). Melting point 141
~ 142 ° C

Intermediate Preparation Example 20 Preparation of 3- (4-chloro-6-fluoro-2-methylbenzofuran-7-yl) -1-methyl-6-trifluoromethyl-2 (1H) -pyridone 3- [ 4-Chloro-2-fluoro-6-propargyloxyphenyl] -1-methyl-6-trifluoromethyl-2 (1H) -pyridone 2.78 g (7.73 mmol)
l) and 2.35 g of cesium fluoride (15.46 mmol)
l) in 180 ml of N, N-diethylaniline in 50 ml
And reacted for 1 hour. After evaporating the solvent under reduced pressure, the residue was extracted with ethyl acetate, and the organic layer was washed with dilute hydrochloric acid. After drying over magnesium sulfate, the solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 0.58 g of the desired product (yield 21%). 138-140 ° C

Intermediate Production Example 21 Production of 3- (2-bromomethyl-7-chloro-5-fluorobenzofuran-4-yl) -1-methyl-6-trifluoromethyl-2- (1H) -pyridone 0.98 g of (7-chloro-5-fluoro-2-methylbenzofuran-4-yl) -1-methyl-6-trifluoromethyl-2- (1H) -pyridone (2.72 mm
ol) was dissolved in 25 ml of carbon tetrachloride and NBS 0.51
g (2.86 mmol) and 0.04 g (0.27 mmol) of 2,2′-azobisisobutyronitrile were added, and the mixture was refluxed for 2 hours. After removing succinimide by filtration,
Carbon tetrachloride was distilled off under reduced pressure, and the obtained residue was poured into water and extracted with ethyl acetate. After washing with water, the organic layer was dried over anhydrous magnesium sulfate. After the ethyl acetate was distilled off under reduced pressure, the obtained crude crystals were washed with n-hexane to obtain 0.94 g (yield 79%) of the desired product. Melting point 142-
144 ° C. ¹ H-NMR (300 MHz, CDCl ₃ ) δ value: 3.
73 (3H, s), 4.56 (2H, s), 6.66
(1H, s), 6.80 (1H, d), 7.20 (1
H, d), 7.55 (1H, d) ppm

Intermediate Production Example 22 Production of 3- (7-chloro-5-fluoro-2-formylbenzofuran-4-yl) -1-methyl-6-trifluoromethyl-2- (1H) -pyridone 15 ml of sulfuric acid To the mixture was added 0.29 g (0.56 mmol) of 3- (7-chloro-2-dibromomethyl-5-fluorobenzofuran-4-yl) -1-methyl-6-trifluoromethyl-2- (1H) -pyridone. After stirring at 50 ° C. for 1 hour, the mixture was poured into water and extracted with diethyl ether.
After washing with water, the organic layer was dried over anhydrous magnesium sulfate. After the ethyl acetate was distilled off under reduced pressure, the obtained crude crystals were washed with n-hexane to obtain 0.20 g of the desired product (yield 9).
6%). ¹ H-NMR (300 MHz, CDCl ₃ ) δ value: 3.
75 (3H, s), 6.84 (1H, d), 7.42
(1H, d), 7.46 (1H, s), 7.61 (1
H, d), 9.90 (1H, s) ppm

Intermediate Preparation Example 23 Preparation of 3- (2-carboxy-7-chloro-5-fluorobenzofuran-4-yl) -1-methyl-6-trifluoromethyl-2- (1H) -pyridone 0.37 g of (7-chloro-5-fluoro-2-formylbenzofuran-4-yl) -1-methyl-6-trifluoromethyl-2- (1H) -pyridone (0.99 m
The mol) was dissolved in acetone 20 ml, was added Jones reagent _(CrO 3 _-H 2 SO ₄₎ at -20 ° C.. -20
After stirring at 2 ° C. for 2 hours, the mixture was poured into water and extracted with ethyl acetate. An aqueous sodium hydroxide solution was added to make the solution alkaline, the aqueous layer was washed with ethyl acetate, and acidified by adding hydrochloric acid.
Extracted with ethyl acetate. After washing with water, the organic layer was dried over anhydrous magnesium sulfate. After the ethyl acetate was distilled off under reduced pressure, the obtained crude crystals were washed with diisopropyl ether to obtain 0.29 g of the desired product (yield 75%). Melting point 2
33-235 ° C. ¹ H-NMR (300 MHz, CDCl ₃ ) δ value: 3.
79 (3H, s), 6.87 (1H, d), 7.38
(1H, d), 7.47 (1H, s), 7.61 (1
H, d) ppm

Intermediate Production Example 24 3- (3-Amino-4-chlorophenyl) -4-chloro-1-methyl-6-trifluoromethyl-2 (1H)-
Production of pyridone 0.5 g of 3- (4-chloro-3-nitrophenyl) -4-chloro-1-methyl-6-trifluoromethyl-2 (1H) -pyridone in 20 ml of ethanol (1.37 mm)
ol), and 0.8 g (6.7 g) of powdered tin was stirred at room temperature.
8 mmol), 3 ml of concentrated hydrochloric acid was added dropwise, and the mixture was stirred for 1 hour. After completion of the reaction, excess ethanol was distilled off under reduced pressure. Ethyl acetate and a saturated aqueous solution of sodium hydrogen carbonate were added, and the precipitate was filtered. Was dried. The organic layer was distilled off under reduced pressure, and the obtained crude crystals were washed with isopropyl ether to obtain 0.40 g (yield 87%) of the desired product. ¹ H-NMR (300 MHz, CDCl ₃ ) δ value: 3.
74 (3H, s), 4.06 (2H, s), 6.54
(1H, dd), 6.59 (1H, s), 6.62 (1
H, d), 7.27 (1H, d) ppm

Intermediate Production Example 25 Production of 4-chloro-2-fluoro-5-methoxybenzyl chloride 2-chloro-4 was added to a methylene chloride solution of 1N titanium tetrachloride.
Dissolve 17.6 g (0.11 mol) of fluoroanisole and add 88.3 methoxymethyl chloride thereto at room temperature.
g (1.10 mol) was added dropwise, followed by stirring at room temperature for 5 hours. After completion of the reaction, the reaction solution was poured into water, stirred at room temperature for 2 hours, and then the aqueous layer was removed. The organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off, and the obtained residue was purified by silica gel column chromatography to obtain the desired product 1
5.5 g (68% yield) were obtained. ¹ H-NMR (300 MHz, CDCl ₃ ) δ value: 3.
89 (3H, s), 5.00 (2H, s), 6.97
(1H, d), 7.18 (1H, d) ppm

Intermediate Production Example 26 Production of 3- (3-amino-4-chloro-6-fluoro-2-hydroxyphenyl) -1-methyl-6-trifluoromethyl-2 (1H) -pyridone 3- ( 4-chloro-6-fluoro-2-hydroxyphenyl) -1-methyl-6-trifluoromethyl-2 (1
H) -Pyridone 3.0 g (13 mmol) in sulfuric acid 20 m
1 g of fuming nitric acid 0.9 g (14 mmol) under ice-cooling.
l) was added dropwise. After stirring for 30 minutes under ice cooling, the reaction solution was poured into ice water, extracted with ethyl acetate, washed with an aqueous solution of sodium hydrogen carbonate and water, dried over anhydrous magnesium sulfate, and the ethyl acetate was distilled off under reduced pressure. I left. The obtained residue was dissolved in 20 ml of ethanol, 5.7 g (48.3 mmol) of powdered tin was added with stirring at room temperature, and 10 ml of concentrated hydrochloric acid was added.
Was added dropwise and stirred for 1 hour. After completion of the reaction, excess ethanol was distilled off under reduced pressure. Ethyl acetate and a saturated aqueous solution of sodium hydrogen carbonate were added, and the precipitate was filtered off.
Washed with aqueous citric acid. After drying the organic layer with anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to obtain the desired product.

Intermediate Production Example 27 3- [7-Chloro-5-fluoro-2- (1-hydroxypropyl) benzofuran-4-yl] -1-methyl-
6-trifluoromethyl-2 (1H) -pyridone 3- [7-chloro-5-fluoro-2- (1-bromopropyl) benzofuran-4-yl] -1-methyl-6
0.13 g of trifluoromethyl-2 (1H) -pyridone
(0.28 mmol) was dissolved in 10 ml of acetone, 5 ml of water and 0.095 g (0.56 mmol) of silver nitrate were added, and the mixture was stirred at room temperature for 1 hour. After removing insolubles by filtration, the solvent was distilled off under reduced pressure, and extracted with ethyl acetate.
The organic layer was washed with water. After drying over anhydrous magnesium sulfate, the residue obtained by evaporating the solvent under reduced pressure was isolated and purified by silica gel column chromatography (hexane: ethyl acetate = 3: 1) to obtain 0.11 g of the desired product (yield 97%). Obtained.
Melting point 103-105 ° C

The herbicide of the present invention comprises a 2-pyridone derivative represented by the general formula [I] as an active ingredient. To use the compound of the present invention as a herbicide, the compound of the present invention itself may be used, but a carrier generally used for formulation,
A surfactant, a dispersant or an auxiliary agent, etc.
It can also be formulated and used in wettable powders, emulsions, fine granules or granules.

The carrier used in the preparation is
Examples include solid carriers such as talc, bentonite, clay, kaolin, diatomaceous earth, white carbon, vermiculite, calcium carbonate, slaked lime, silica sand, ammonium sulfate, and urea, and liquid carriers such as isopropyl alcohol, xylene, cyclohexane, and methylnaphthalene.

Examples of surfactants and dispersants include metal salts of alkyl benzene sulfonic acid, metal salts of dinaphthyl methane disulfonic acid, alcohol sulfates, alkyl aryl sulfonates, lignin sulfonates, polyoxyethylene glycol ethers and polyoxyethylene glycol ethers. Oxyethylene alkyl aryl ether, polyoxyethylene sorbitan monoalkylate and the like can be mentioned. Examples of the adjuvant include carboxymethyl cellulose, polyethylene glycol, gum arabic and the like. When used, they are diluted to an appropriate concentration and sprayed or applied directly.

The herbicide of the present invention can be used by foliage application, soil application or surface application. The compounding ratio of the active ingredient is appropriately selected as necessary, but when it is a powder or granule, it is appropriately selected from the range of 0.01 to 10% (weight), preferably 0.05 to 5% (weight). Is good. 1 to 50% when used as emulsion and wettable powder
(Weight), preferably from 5 to 30% (weight).

The application rate of the herbicide of the present invention varies depending on the kind of the compound used, the target weed, the tendency to emerge, the environmental conditions, the dosage form used, and the like. The active ingredient may be appropriately selected from the range of 0.1 g to 5 kg, preferably 1 g to 1 kg per 10 ares. Further, when used in a liquid form such as an emulsion and a wettable powder, 0.1 to 50,000 p.
pm, preferably in the range of 10 to 10,000 ppm.

The compounds of the present invention may be used as needed with insecticides, fungicides, other herbicides, plant growth regulators, fertilizers and the like.

Next, the preparation method will be specifically described with reference to typical preparation examples. The types and compounding ratios of the compounds and additives are not limited to these and can be changed in a wide range. In the following description, “parts” means parts by weight.

<Formulation Example 1> Water-dispersible agent 10 parts of compound (1-1), 0.5 parts of polyoxyethylene octylphenyl ether, 0.5 parts of sodium salt of β-naphthalenesulfonic acid formalin condensate, diatomaceous earth Are mixed and pulverized to obtain a wettable powder.

<Preparation Example 2> Wettable powder 0.5 parts of polyoxyethylene octylphenyl ether, 0.5 parts of sodium salt of β-naphthalenesulfonic acid formalin condensate, 10 parts of compound (1-1), diatomaceous earth And 5 parts of white carbon and 64 parts of clay are mixed and pulverized to obtain a wettable powder.

Formulation Example 3 Wettable powder: 10 parts of compound (1-1), 0.5 parts of polyoxyethylene octylphenyl ether, 0.5 parts of sodium salt of β-naphthalenesulfonic acid formalin condensate, diatomaceous earth And 5 parts of white carbon and 64 parts of calcium carbonate are mixed and pulverized to obtain a wettable powder.

Formulation Example 4 Emulsion 30 parts of compound (1-1), 60 parts of an equal mixture of xylene and isophorone, surfactant polyoxyethylene sorbitan alkylate, polyoxyethylene alkylaryl polymer and alkylaryl sulfonate An emulsion is obtained by adding 10 parts of the mixture and stirring them well.

Formulation Example 5 Granules 10 parts of compound (1-1), 80 parts of a bulking agent obtained by mixing talc and bentonite at a ratio of 1: 3, 5 parts of white carbon, surfactant polyoxyethylene 5 of a mixture of sorbitan alkylate, polyoxyethylene alkylaryl polymer and alkylaryl sulfonate
Then, 10 parts of water was added to the mixture, and the mixture was kneaded well and extruded from a sieve hole having a diameter of 0.7 mm, dried, and then cut to a length of 0.5 to 1 mm to obtain granules.

Next, the effects of the compound of the present invention will be described with reference to Test Examples. The following compounds were used as comparative agents.

[0271]

Embedded image

<Test Example 1> Herbicidal effect test by paddy field soil treatment A 100 cm ² plastic pot was filled with paddy field soil, water-filled and scratched, and then the seeds of Echinacea purpurea (Ec) and konagi (M)
o) and fireflies (Sc).
m. The next day, the wettable powder prepared according to Formulation Example 1 was diluted with water and dropped on the water surface. The application rate is 1 active ingredient.
100 g per 0 ares. Thereafter, the plants were grown in a greenhouse, and on the 21st day after the treatment, the herbicidal effect was examined according to the criteria in Table 62. The results are shown in Tables 63 to 67.

[0273]

[Table 62]

[0274]

[Table 63]

[0275]

[Table 64]

[0276]

[Table 65]

[0277]

[Table 66]

[0278]

[Table 67]

<Test Example 2> Herbicidal effect test by upland soil treatment A sand was filled in a 120 cm ² plastic pot, and was used for barnyardgrass (Ec), crabgrass (Di), porpoise (Po),
Various seeds of Aobeyu (Am), Shiroza (Ch) and Kogomegatsuri (Ci) were sown and covered with soil. The wettable powder prepared according to Formulation Example 1 was diluted with water, and 100 l per 10 ares was evenly sprayed on the soil surface with a small sprayer so that the active ingredient was 100 g per 10 ares. Thereafter, the plants were grown in a greenhouse, and on the 21st day of the treatment, the herbicidal effects were investigated according to the criteria in Table 62. The results are shown in Tables 68 to 69. -Represents untested.

[0280]

[Table 68]

[0281]

[Table 69]

[0282] <Test Example 3> The field soil was filled in herbicidal effect test 80 cm ² plastic pots by upland field soil treatment, Enokoro (Se), and covered with soil and seeded each seed of slender amaranth (Am). The wettable powder prepared according to Formulation Example 1 was diluted with water, and the active ingredient was diluted so that the active ingredient was 6.3 g per 10 ares.
100 l per 0 ares was evenly sprayed on the soil surface with a small sprayer. Thereafter, the plants were grown in a greenhouse, and on the 21st day of the treatment, the herbicidal effects were investigated according to the criteria in Table 62. Table 7 shows the results
0 to Table 71. In addition,-represents an untested.

[0283]

[Table 70]

[0284]

[Table 71]

<Test Example 4> Test of herbicidal effect by upland foliage treatment A plastic pot of 120 cm ² was filled with sand, and crabgrass (Di), giant oak (Po), and bluegrass (A) were filled.
m), various seeds of Shiroza (Ch) and Kogo Megatsuri (Ci) were sown and grown for 2 weeks in a greenhouse, and then the wettable powder prepared according to Formulation Example 1 was diluted with water to obtain an active ingredient per 10 ares. 100 l per 10 ares was foliage-sprayed from above the whole plant with a small sprayer so that the total weight would be 100 g. Thereafter, the plants were grown in a greenhouse, and on the 14th day of the treatment, the herbicidal effect was investigated according to the criteria in Table 62. Tables 72 to 7 show the results.
It is shown in FIG.

[0286]

[Table 72]

[0287]

[Table 73]

[0288]

[Table 74]

[0289] <Test Example 5> The field soil was filled in herbicidal effect test 80 cm ² plastic pots by upland field foliage treatment, velvetleaf (Ab), were covered with soil and seeded each seed of slender amaranth (Am). The wettable powder prepared according to Formulation Example 1 was diluted with water,
100 l per 10 ares was spray-foliated from the top of the plant using a small sprayer so that the active ingredient was 6.3 g per 10 ares. Then, it is grown in a greenhouse and treated 1
On the fourth day, the herbicidal effect was examined according to the criteria in Table 62.
The results are shown in Tables 75 to 77.

[0290]

[Table 75]

[0291]

[Table 76]

[0292]

[Table 77]

[0293]

Industrial Applicability The compound of the present invention represented by the general formula [I] is useful for various weeds which are problematic in the field, for example, P. occidentalis, Aoubiyu, Shiroza, Hakobe, Ichibi, American stag, American hornflower, Asagao, Perennial and annual perennial cyperaceous weeds, including broadleaf weeds such as firgrass, hamazuge, yellow clover, cornflower, cyperaceae, and kogomegatsuri, barnyardgrass, johnsongrass, johnsongrass, hornwort, etc. It has an excellent herbicidal effect over a wide range of growing seasons. In addition, Tainubie, Tamayatsuri which occurs in paddy field,
It can also control annual weeds such as pearls and perennial weeds such as urikawa, omodaka, shrew beetle, kuroguwai, fireflies, and spoongrass.

On the other hand, the herbicide of the present invention has high safety against crops, and particularly shows high safety against rice, wheat, barley, corn, grain sorghum, soybean, cotton, sugar beet and the like.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁶ Identification code FI C07D 405/10 213 C07D 405/10 213 405/14 213 405/14 213 409/10 213 409/10 213 409/14 213 409 / 14 213 411/14 411/14 413/04 213 413/04 213 417/04 213 417/04 213 (72) Inventor Atsushi Shibayama 408 Shionita, Fukuda-cho, Fukuda-cho, Iwata-gun, Shizuoka Pref. In-house (72) Inventor Mitsuhiro Yamaji 1809 Kamo Kikugawa-cho, Ogasa-gun, Shizuoka Prefecture (72) Inventor Ryo Hanai 2-26-35, Nishihara, Asa-minami-ku, Hiroshima-shi, Hiroshima-103 (72) Inventor Sota Uozu Ogasa, Shizuoka Prefecture 3353 Kamo, Kikugawa-cho, Gunma (72) Inventor Hideo Sadohara 2-9-9 Horinouchi, Niiza-shi, Saitama

Claims (5)

[Claims] 1. A compound of the general formula [I] In the formula, R ¹ is a hydrogen atom, an alkyl group, a haloalkyl group, an acetyl group, a group —N ＝ CR ¹² R ¹³ or a group —NR
¹⁷ R ¹⁸ , wherein R ¹² and R ¹³ are each independently a hydrogen atom, an alkyl group, a group —NR ¹⁷ R ¹⁸ or a phenyl group (the group is substituted with a halogen atom, a nitro group, an alkyl group, a haloalkyl group or an alkoxy group) R ¹⁷ and R ¹⁸ each independently represent a hydrogen atom, an alkyl group, a haloalkyl group, an acyl group, an alkoxycarbonyl group, a benzoyl group (the group is a halogen atom, a nitro group, an alkyl group, A haloalkyl group or an alkoxy group; a phenoxycarbonyl group (the group may be substituted with a halogen atom, a nitro group, an alkyl group, a haloalkyl group or an alkoxy group), a formyl group or an alkyl group; Represents a sulfonyl group. R ² represents a haloalkyl group; R ³ represents a hydrogen atom, an alkyl group, a carboxyl group or an alkoxycarbonyl group; R ⁴ represents a hydrogen atom, a halogen atom, an alkoxy group, a cyano group or an alkyl group; Embedded image Wherein, ^{R 5} represents a hydrogen atom or a halogen atom, ^{R 6}
Represents a hydrogen atom, a halogen atom, a nitro group or a cyano group, R ⁷ represents an acylalkoxy group, a dialkoxyalkoxy group, a dialkoxyalkylthio group, a hydroxycycloalkyloxy group, an alkoxycycloalkyloxy group, an acyloxycycloalkyloxy group, Alkoxycarbonyloxycycloalkyloxy group, cycloalkenyloxy group, acylamino group, dialkoxycarbonylalkylthio group, dialkoxycarbonylalkoxy group, dialkoxyphosphonylalkyl group, epoxycycloalkyl group, (alkenyloxy group, alkylsulfonyloxy group or A cycloalkyl group (substituted with an alkyl group) or a general formula Represents a group represented by the formula, Y is an oxygen atom, a sulfur atom or a group -NR ^17, Het is 3- to 6-membered heterocyclic ring (in which a halogen atom, a nitro group, an oxo group, an alkyl group, R ¹⁴ represents a hydrogen atom, an alkyl group or a cycloalkyl group, R ¹⁵ represents an alkoxyalkoxyalkyl group, an alkoxycarbonylalkyl group,
Alkenyloxycarbonylalkyl group, alkynyloxycarbonylalkyl group, cycloalkyloxycarbonylalkyl group, alkoxyalkoxycarbonylalkyl group, haloalkoxycarbonylalkyl group, haloalkenyloxycarbonylalkyl group, benzyloxycarbonylalkyl group (the benzyl group of the group is May be substituted with a halogen atom, nitro group, alkyl group, haloalkyl group or alkoxy group.), Alkylthiocarbonylalkyl group, alkylsulfinylalkoxycarbonylalkyl group, alkylsulfonylalkoxycarbonylalkyl group, monoalkylcarbamoylalkyl group, dialkyl Carbamoylalkyl group, alkylthioalkoxycarbonylalkyl group, phenoxycarbonylalkyl Group (the phenyl group of the group are a halogen atom, a nitro group, an alkyl group, optionally substituted haloalkyl group or alkoxy group.), Alkoxycarbonyl alkoxycarbonylalkyl radical, R
²⁰ represents a hydrogen atom, a halogen atom or an alkyl group.
R ⁸ represents a hydrogen atom, a halogen atom, a hydroxyl group, an alkoxy group, an alkenyloxy group, an alkynyloxy group,
Haloalkoxy groups, haloalkenyloxy group, an alkoxycarbonyl group or a group -NR ¹⁷ R ^18, Y are as defined above, R ⁹ is an alkoxy group, a haloalkoxy group, an alkenyloxy group, a halo alkenyloxy group, Alkynyloxy group, alkoxycarbonylalkoxy group, haloalkylthio group, alkenylthio group, alkynylthio group, alkoxycarbonylalkylthio group,
Alkylsulfonyl group, haloalkylsulfonyl group, optionally substituted phenylsulfonyl group, hydroxyiminoalkyl group, hydroxyiminohaloalkyl group,
Alkoxyiminoalkyl group, alkoxyiminohaloalkyl group, alkyliminoalkyl group, optionally substituted phenyliminoalkyl group, hydrazonoalkyl group, alkylhydrazonoalkyl group, optionally substituted phenylhydrazonoalkyl group, substituted Optionally substituted phenyl group, optionally substituted benzyl group, cyanoalkyl group, carbamoylalkyl group, thiocyanatoalkyl group, nitro group, hydroxyamino group, oxiranyl group optionally substituted by alkyl group or General formula (Wherein, R ²⁰ represents the same meaning as described above, and R ²¹ represents a hydrogen atom, an alkyl group, an alkoxy group, a cycloalkyl group,
Alkenyl group, alkynyl group, haloalkyl group, alkoxyalkyl group, haloalkoxy group, alkenyloxy group, alkynyloxy group, alkoxycarbonylalkoxy group, alkylthio group, haloalkylthio group, alkenylthio group, alkynylthio group, alkoxycarbonylalkylthio group, Represents an alkylsulfonyl group, a haloalkylsulfonyl group, an optionally substituted phenylsulfonyl group, a hydroxyiminoalkyl group, a hydroxyiminohaloalkyl group or an alkylthioalkyl group, or R ²⁰ and R ²¹ are bonded to each other, Together with the carbon atoms present therefrom can form a 3- to 8-membered (carbon) ring. R ²² represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group,
Alkoxyalkyl group, haloalkyl group, haloalkenyl group, cyanoalkyl group, alkylthioalkyl group, alkylsulfonylalkyl group, alkylsulfinylalkyl group, alkoxycarbonylalkyl group, haloalkoxycarbonylalkyl group, carbonylalkyl group,
Carboxyalkyl, monoalkylcarbamoylalkyl, dialkylcarbamoylalkyl, acyl, alkylsulfonyl, haloalkylsulfonyl, alkoxycarbonyl, haloalkylcarbonyl, monoalkylcarbamoyl, (monoalkyl) thiocarbamoyl, dialkylcarbamoyl , (Dialkyl) thiocarbamoyl group or a benzoyl group which may be substituted. However, when R ²² is a hydrogen atom, an alkyl group or a haloalkyl group, R ²¹ excludes a hydrogen atom or an alkyl group. R ²³ is a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an alkoxyalkyl group, a haloalkenyl group, an alkoxycarbonyl group, a cycloalkyl group, a haloalkyl group, an alkoxycarbonylalkyl group, a hydroxycarbonylalkyl group, a monoalkylcarbamoylalkyl group, Dialkylcarbamoylalkyl group, acyl group, alkylsulfonyl group, haloalkylsulfonyl group, optionally substituted benzenesulfonyl group, optionally substituted benzylsulfonyl group,
Haloalkylcarbonyl group, cycloalkylcarbonyl group, alkenylcarbonyl group, alkynylcarbonyl group, alkoxycarbonyl group, monoalkylcarbamoyl group, (monoalkyl) thiocarbamoyl group, dialkylcarbamoyl group, (dialkyl) thiocarbamoyl group, even if substituted Represents a good phenyl group or a benzoyl group which may be substituted, and R ²⁴ represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an alkoxyalkyl group, a haloalkenyl group, an alkoxycarbonyl group,
Cycloalkyl group, haloalkyl group, alkoxycarbonylalkyl group, hydroxycarbonylalkyl group, monoalkylcarbamoylalkyl group, dialkylcarbamoylalkyl group, acyl group, formyl group, alkylsulfonyl group, haloalkylsulfonyl group, haloalkylcarbonyl group, alkoxycarbonyl group, Represents a monoalkylcarbamoyl group, a (monoalkyl) thiocarbamoyl group, a dialkylcarbamoyl group, a (dialkyl) thiocarbamoyl group or an optionally substituted benzoyl group, or R ²³ and R ²⁴ are bonded to each other, and Together with the present nitrogen atom can form a 3- to 8-membered (carbon) ring. R ²⁵ is a hydrogen atom, a hydroxyl group, an alkyl group, an alkoxy group, a cycloalkyl group, an alkenyl group, an alkynyl group, a haloalkyl group, an alkoxyalkyl group, a haloalkoxy group, an alkenyloxy group, an alkynyloxy group, an alkoxycarbonylalkoxy group, an alkylthio group. Group, haloalkylthio group, alkenylthio group, alkynylthio group, alkoxycarbonylalkylthio group, alkylsulfonyl group, haloalkylsulfonyl group, optionally substituted phenylsulfonyl group, hydroxyiminoalkyl group, hydroxyiminohaloalkyl group, alkylthioalkyl group or the group ^-NR 23 ^{R 24} (wherein ^{each R 23} and ^{R 24} are as defined above.) ^{represents, R 26} is a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group Cycloalkyl, alkenyl, alkynyl, haloalkyl, alkoxyalkyl, haloalkoxy, alkenyloxy, alkynyloxy, alkoxycarbonylalkoxy, alkylthio, haloalkylthio, alkenylthio, alkynylthio, carboxyl Group, an alkoxycarbonyl group, an alkenyloxycarbonyl group or an alkynyloxycarbonyl group. R ¹⁰ represents a hydrogen atom, an alkyl group, a haloalkyl group, an acyl group, a halogen atom or a nitro group, and R ¹¹ represents a hydrogen atom, a hydroxyl group, a thiol group,
Alkyl group, halogen atom, cycloalkyl group, alkenyl group, alkynyl group, haloalkyl group, cyano group, alkoxycarbonyl group, carboxyl group, alkenyloxycarbonyl group, alkynyloxycarbonyl group, haloalkoxycarbonyl group, cycloalkyloxycarbonyl group, Alkoxyalkyloxycarbonyl group, formyl group, acyl group, alkoxy group, haloalkoxy group, alkenyloxy group, haloalkenyl group, alkynyloxy group, alkoxycarbonylalkoxy group, alkylthio group, haloalkylthio group, alkenylthio group,
Alkynylthio, alkoxycarbonylalkylthio, alkylsulfonyl, haloalkylsulfonyl, optionally substituted phenylsulfonyl, hydroxyiminoalkyl, hydroxyiminohaloalkyl, alkoxyiminoalkyl, alkoxyiminohaloalkyl, alkyliminoalkyl Group, optionally substituted phenyliminoalkyl group, hydrazonoalkyl group, alkylhydrazonoalkyl group, optionally substituted phenylhydrazonoalkyl group, optionally substituted phenyl group, optionally substituted A good benzyl group, a cyanoalkyl group, a carbamoylalkyl group, a cyanoalkylthio group, a nitro group, a hydroxyamino group, an oxiranyl group optionally substituted by an alkyl group, or a compound represented by the general formula: (Wherein, R ²⁰ , R ²¹ , R ²³ , R ²⁴ , R ²⁵ , R
²⁶ and n each have the same meaning as described above, and R ^{22 ′}
Is a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, an alkoxyalkyl group, a haloalkyl group, a haloalkenyl group, a cyanoalkyl group, an alkylthioalkyl group, an alkylsulfonylalkyl group,
Alkylsulfinylalkyl group, alkoxycarbonylalkyl group, haloalkoxycarbonylalkyl group,
Carbonylalkyl group, carboxyalkyl group, monoalkylcarbamoylalkyl group, dialkylcarbamoylalkyl group, acyl group, alkylsulfonyl group, haloalkylsulfonyl group, alkoxycarbonyl group, haloalkylcarbonyl group, monoalkylcarbamoyl group,
It represents a (monoalkyl) thiocarbamoyl group, a dialkylcarbamoyl group, a (dialkyl) thiocarbamoyl group or a benzoyl group which may be substituted. ). ]
Represents 2-pyridone derivatives represented by｝. 2. A compound of the general formula [I] In the formula, R ¹ is a hydrogen atom, an alkyl group, a haloalkyl group, an acetyl group, a group —N ＝ CR ¹² R ¹³ or a group —NR
¹⁷ R ¹⁸ , wherein R ¹² and R ¹³ are each independently a hydrogen atom, an alkyl group, a group —NR ¹⁷ R ¹⁸ or a phenyl group (the group is substituted with a halogen atom, a nitro group, an alkyl group, a haloalkyl group or an alkoxy group) R ¹⁷ and R ¹⁸ each independently represent a hydrogen atom, an alkyl group, a haloalkyl group, an acyl group, an alkoxycarbonyl group, a benzoyl group (the group is a halogen atom, a nitro group, an alkyl group, A haloalkyl group or an alkoxy group; a phenoxycarbonyl group (the group may be substituted with a halogen atom, a nitro group, an alkyl group, a haloalkyl group or an alkoxy group), a formyl group or an alkyl group; Represents a sulfonyl group. R ² represents a haloalkyl group; R ³ represents a hydrogen atom, an alkyl group, a carboxyl group or an alkoxycarbonyl group; R ⁴ represents a hydrogen atom, a halogen atom, an alkoxy group, a cyano group or an alkyl group; Embedded image Wherein, ^{R 5} represents a hydrogen atom or a halogen atom, ^{R 6}
Represents a hydrogen atom, a halogen atom, a nitro group or a cyano group, R ⁷ represents an acylalkoxy group, a dialkoxyalkoxy group, a dialkoxyalkylthio group, a hydroxycycloalkyloxy group, an alkoxycycloalkyloxy group, an acyloxycycloalkyloxy group, An alkoxycarbonyloxycycloalkyloxy group, a cycloalkenyloxy group or a general formula Represents a group represented by the formula, Y is an oxygen atom, a sulfur atom or a group -NR ^17, Het is 3- to 6-membered heterocyclic ring (in which a halogen atom, a nitro group, an oxo group, an alkyl group, R ¹⁴ represents a hydrogen atom, an alkyl group or a cycloalkyl group, R ¹⁵ represents an alkoxyalkoxyalkyl group, an alkoxycarbonylalkyl group,
Alkenyloxycarbonylalkyl group, alkynyloxycarbonylalkyl group, cycloalkyloxycarbonylalkyl group, alkoxyalkoxycarbonylalkyl group, haloalkoxycarbonylalkyl group, haloalkenyloxycarbonylalkyl group, benzyloxycarbonylalkyl group (the benzyl group of the group is May be substituted with a halogen atom, nitro group, alkyl group, haloalkyl group or alkoxy group.), Alkylthiocarbonylalkyl group, alkylsulfinylalkoxycarbonylalkyl group, alkylsulfonylalkoxycarbonylalkyl group, monoalkylcarbamoylalkyl group, dialkyl Carbamoylalkyl group, alkylthioalkoxycarbonylalkyl group, phenoxycarbonylalkyl Group (the phenyl group of the group are a halogen atom, a nitro group, an alkyl group, optionally substituted haloalkyl group or alkoxy group.), Alkoxycarbonyl alkoxycarbonylalkyl radical, R
²⁰ represents a hydrogen atom, a halogen atom or an alkyl group.
R ⁸ represents a hydrogen atom, a halogen atom, a hydroxyl group, an alkoxy group, an alkenyloxy group, an alkynyloxy group,
Haloalkoxy group, haloalkenyloxy group or group -N
R ¹⁷ represents R ¹⁸ , Y represents the same meaning as described above, and R ⁹ represents
Is an alkoxy group, haloalkoxy group, alkenyloxy group, haloalkenyloxy group, alkynyloxy group, alkoxycarbonylalkoxy group, haloalkylthio group, alkenylthio group, alkynylthio group, alkoxycarbonylalkylthio group, alkylsulfonyl group, haloalkylsulfonyl group An optionally substituted phenylsulfonyl group, hydroxyiminoalkyl group, hydroxyiminohaloalkyl group, alkoxyiminoalkyl group, alkoxyiminohaloalkyl group, alkyliminoalkyl group, optionally substituted phenyliminoalkyl group, hydrazonoalkyl Group, alkylhydrazonoalkyl group, optionally substituted phenylhydrazonoalkyl group, optionally substituted phenyl group, optionally substituted benzyl Group, cyanoalkyl group, carbamoyl group, thiocyanatoalkyl alkyl group, a nitro group,
A hydroxyamino group, an oxiranyl group which may be substituted by an alkyl group, or a general formula: (Wherein, R ²⁰ represents the same meaning as described above, and R ²¹ represents a hydrogen atom, an alkyl group, an alkoxy group, a cycloalkyl group,
Alkenyl group, alkynyl group, haloalkyl group, alkoxyalkyl group, haloalkoxy group, alkenyloxy group, alkynyloxy group, alkoxycarbonylalkoxy group, alkylthio group, haloalkylthio group, alkenylthio group, alkynylthio group, alkoxycarbonylalkylthio group, Represents an alkylsulfonyl group, a haloalkylsulfonyl group, an optionally substituted phenylsulfonyl group, a hydroxyiminoalkyl group, a hydroxyiminohaloalkyl group or an alkylthioalkyl group, or R ²⁰ and R ²¹ are bonded to each other, Together with the carbon atoms present therefrom can form a 3- to 8-membered (carbon) ring. R ²² represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group,
Alkoxyalkyl group, haloalkyl group, haloalkenyl group, cyanoalkyl group, alkylthioalkyl group, alkylsulfonylalkyl group, alkylsulfinylalkyl group, alkoxycarbonylalkyl group, haloalkoxycarbonylalkyl group, carbonylalkyl group,
Carboxyalkyl, monoalkylcarbamoylalkyl, dialkylcarbamoylalkyl, acyl, alkylsulfonyl, haloalkylsulfonyl, alkoxycarbonyl, haloalkylcarbonyl, monoalkylcarbamoyl, (monoalkyl) thiocarbamoyl, dialkylcarbamoyl , (Dialkyl) thiocarbamoyl group or a benzoyl group which may be substituted. However, when R ²² is a hydrogen atom, an alkyl group or a haloalkyl group, R ²¹ excludes a hydrogen atom or an alkyl group. R ²³ is a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an alkoxyalkyl group, a haloalkenyl group, an alkoxycarbonyl group, a cycloalkyl group, a haloalkyl group, an alkoxycarbonylalkyl group, a hydroxycarbonylalkyl group, a monoalkylcarbamoylalkyl group, Dialkylcarbamoylalkyl group, acyl group, alkylsulfonyl group, haloalkylsulfonyl group, optionally substituted benzenesulfonyl group, optionally substituted benzylsulfonyl group,
Haloalkylcarbonyl group, cycloalkylcarbonyl group, alkenylcarbonyl group, alkynylcarbonyl group, alkoxycarbonyl group, monoalkylcarbamoyl group, (monoalkyl) thiocarbamoyl group, dialkylcarbamoyl group, (dialkyl) thiocarbamoyl group, even if substituted Represents a good phenyl group or a benzoyl group which may be substituted, and R ²⁴ represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an alkoxyalkyl group, a haloalkenyl group, an alkoxycarbonyl group,
Cycloalkyl group, haloalkyl group, alkoxycarbonylalkyl group, hydroxycarbonylalkyl group, monoalkylcarbamoylalkyl group, dialkylcarbamoylalkyl group, acyl group, formyl group, alkylsulfonyl group, haloalkylsulfonyl group, haloalkylcarbonyl group, alkoxycarbonyl group, Represents a monoalkylcarbamoyl group, a (monoalkyl) thiocarbamoyl group, a dialkylcarbamoyl group, a (dialkyl) thiocarbamoyl group or an optionally substituted benzoyl group, or R ²³ and R ²⁴ are bonded to each other, and Together with the present nitrogen atom can form a 3- to 8-membered (carbon) ring. R ²⁵ is a hydrogen atom, a hydroxyl group, an alkyl group, an alkoxy group, a cycloalkyl group, an alkenyl group, an alkynyl group, a haloalkyl group, an alkoxyalkyl group, a haloalkoxy group, an alkenyloxy group, an alkynyloxy group, an alkoxycarbonylalkoxy group, an alkylthio group. Group, haloalkylthio group, alkenylthio group, alkynylthio group, alkoxycarbonylalkylthio group, alkylsulfonyl group, haloalkylsulfonyl group, optionally substituted phenylsulfonyl group, hydroxyiminoalkyl group, hydroxyiminohaloalkyl group, alkylthioalkyl group or the group ^-NR 23 ^{R 24} (wherein ^{each R 23} and ^{R 24} are as defined above.) ^{represents, R 26} is a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group Cycloalkyl, alkenyl, alkynyl, haloalkyl, alkoxyalkyl, haloalkoxy, alkenyloxy, alkynyloxy, alkoxycarbonylalkoxy, alkylthio, haloalkylthio, alkenylthio, alkynylthio, carboxyl Group, an alkoxycarbonyl group, an alkenyloxycarbonyl group or an alkynyloxycarbonyl group. R ¹⁰ represents a hydrogen atom, an alkyl group, a haloalkyl group, an acyl group, a halogen atom or a nitro group, and R ¹¹ represents a hydrogen atom, a hydroxyl group, a thiol group,
Alkyl group, halogen atom, cycloalkyl group, alkenyl group, alkynyl group, haloalkyl group, cyano group, alkoxycarbonyl group, carboxyl group, alkenyloxycarbonyl group, alkynyloxycarbonyl group, haloalkoxycarbonyl group, cycloalkyloxycarbonyl group, Alkoxyalkyloxycarbonyl group, formyl group, acyl group, alkoxy group, haloalkoxy group, alkenyloxy group, haloalkenyl group, alkynyloxy group, alkoxycarbonylalkoxy group, alkylthio group, haloalkylthio group, alkenylthio group,
Alkynylthio, alkoxycarbonylalkylthio, alkylsulfonyl, haloalkylsulfonyl, optionally substituted phenylsulfonyl, hydroxyiminoalkyl, hydroxyiminohaloalkyl, alkoxyiminoalkyl, alkoxyiminohaloalkyl, alkyliminoalkyl Group, optionally substituted phenyliminoalkyl group, hydrazonoalkyl group, alkylhydrazonoalkyl group, optionally substituted phenylhydrazonoalkyl group, optionally substituted phenyl group, optionally substituted A good benzyl group, a cyanoalkyl group, a carbamoylalkyl group, a cyanoalkylthio group, a nitro group, a hydroxyamino group, an oxiranyl group optionally substituted by an alkyl group, or a compound represented by the general formula: (Wherein, R ²⁰ , R ²¹ , R ²³ , R ²⁴ , R ²⁵ , R
²⁶ and n each have the same meaning as described above, and R ^{22 ′}
Is a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, an alkoxyalkyl group, a haloalkyl group, a haloalkenyl group, a cyanoalkyl group, an alkylthioalkyl group, an alkylsulfonylalkyl group,
Alkylsulfinylalkyl group, alkoxycarbonylalkyl group, haloalkoxycarbonylalkyl group,
Carbonylalkyl group, carboxyalkyl group, monoalkylcarbamoylalkyl group, dialkylcarbamoylalkyl group, acyl group, alkylsulfonyl group, haloalkylsulfonyl group, alkoxycarbonyl group, haloalkylcarbonyl group, monoalkylcarbamoyl group,
It represents a (monoalkyl) thiocarbamoyl group, a dialkylcarbamoyl group, a (dialkyl) thiocarbamoyl group or a benzoyl group which may be substituted. ). ]
Represents 2-pyridone derivatives represented by｝. 3. A compound of the general formula [I] In the formula, R ¹ is a hydrogen atom, an alkyl group, a haloalkyl group, an acetyl group, a group —N ＝ CR ¹² R ¹³ or a group —NR
¹⁷ R ¹⁸ , wherein R ¹² and R ¹³ are each independently a hydrogen atom, an alkyl group, a group —NR ¹⁷ R ¹⁸ or a phenyl group (the group is substituted with a halogen atom, a nitro group, an alkyl group, a haloalkyl group or an alkoxy group) R ¹⁷ and R ¹⁸ each independently represent a hydrogen atom, an alkyl group, a haloalkyl group, an acyl group, an alkoxycarbonyl group, a benzoyl group (the group is a halogen atom, a nitro group, an alkyl group, A haloalkyl group or an alkoxy group; a phenoxycarbonyl group (the group may be substituted with a halogen atom, a nitro group, an alkyl group, a haloalkyl group or an alkoxy group), a formyl group or an alkyl group; Represents a sulfonyl group. R ² represents a haloalkyl group; R ³ represents a hydrogen atom, an alkyl group, a carboxyl group or an alkoxycarbonyl group; R ⁴ represents a hydrogen atom, a halogen atom, an alkoxy group, a cyano group or an alkyl group; Embedded image Wherein, ^{R 5} represents a hydrogen atom or a halogen atom, ^{R 6}
Represents a hydrogen atom, a halogen atom, a nitro group or a cyano group, R ⁷ represents an acylamino group, a dialkoxycarbonylalkylthio group, a dialkoxycarbonylalkoxy group,
A dialkoxyphosphonylalkyl group, an epoxycycloalkyl group, a cycloalkyl group (alkenyloxy group, alkylsulfonyloxy group or alkyl-substituted) or a general formula (Wherein, R ²⁰ represents a hydrogen atom, a halogen atom or an alkyl group, and R ²⁵ represents a hydrogen atom, a hydroxyl group, an alkyl group, an alkoxy group, a cycloalkyl group, an alkenyl group, an alkynyl group, a haloalkyl group, an alkoxyalkyl group, Haloalkoxy group, alkenyloxy group, alkynyloxy group, alkoxycarbonylalkoxy group, alkylthio group, haloalkylthio group, alkenylthio group, alkynylthio group, alkoxycarbonylalkylthio group, alkylsulfonyl group, haloalkylsulfonyl group, even if substituted phenyl sulfonyl group, hydroxyimino group, hydroxyimino haloalkyl group, an alkylthioalkyl group or a group -NR ²³ R
²⁴ (wherein, R ²³ represents R ²⁴ represents a hydrogen atom, an alkyl group,
Alkenyl group, alkynyl group, alkoxyalkyl group,
Haloalkenyl group, alkoxycarbonyl group, cycloalkyl group, haloalkyl group, alkoxycarbonylalkyl group, hydroxycarbonylalkyl group, monoalkylcarbamoylalkyl group, dialkylcarbamoylalkyl group, acyl group, formyl group, alkylsulfonyl group, haloalkylsulfonyl group, Optionally substituted benzenesulfonyl, optionally substituted benzylsulfonyl, haloalkylcarbonyl, cycloalkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, alkoxycarbonyl, monoalkylcarbamoyl, (monoalkyl) A thiocarbamoyl group, a dialkylcarbamoyl group, a (dialkyl) thiocarbamoyl group, an optionally substituted phenyl group, or an optionally substituted Represents a benzoyl group, R ²⁴ is a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an alkoxyalkyl group, a haloalkenyl group, an alkoxycarbonyl group, a cycloalkyl group, a haloalkyl group, an alkoxycarbonylalkyl group, hydroxycarbonyl group, mono Alkylcarbamoylalkyl group, dialkylcarbamoylalkyl group, acyl group, formyl group,
Represents an alkylsulfonyl group, a haloalkylsulfonyl group, a haloalkylcarbonyl group, an alkoxycarbonyl group, a monoalkylcarbamoyl group, a (monoalkyl) thiocarbamoyl group, a dialkylcarbamoyl group, a (dialkyl) thiocarbamoyl group or a benzoyl group which may be substituted. , R ²⁶ represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a cycloalkyl group, an alkenyl group, an alkynyl group, a haloalkyl group, an alkoxyalkyl group, a haloalkoxy group, an alkenyloxy group, an alkynyloxy group, an alkoxycarbonylalkoxy group,
Represents an alkylthio group, a haloalkylthio group, an alkenylthio group, an alkynylthio group, a carboxyl group, an alkoxycarbonyl group, an alkenyloxycarbonyl group or an alkynyloxycarbonyl group. ). R ⁸ represents a hydrogen atom, a halogen atom, a hydroxyl group, an alkoxy group,
Represents an alkenyloxy group, an alkynyloxy group, a haloalkoxy group, a haloalkenyloxy group, an alkoxycarbonylalkyl group, or a group -NR ¹⁷ R ¹⁸ . ]. 2-pyridone derivatives represented by｝. 4. A compound of the general formula [I '] In the formula, R ^{1 ′} represents a hydrogen atom, an alkyl group or a haloalkyl group, R ^{3 ′} represents a hydrogen atom or an alkyl atom, and Q ′ has the general formula: [Wherein, R ^{5 ′} represents a hydrogen atom or a halogen atom;
^{6 ′} represents a halogen atom or a cyano group, R ^{7 ′} represents a hydrogen atom, a halogen atom, a nitro group, an alkoxy group, an alkenyloxy group, a phenyloxy group, an amino group, a hydroxy group, an alkoxyalkylthio group, an alkynyloxy group, Alkoxy group, alkoxyalkoxy group, acylalkoxy group, alkoxycarbonylalkoxy group, alkoxycarbonylhaloalkoxy group, cycloalkoxy group, alkylaminocarbonylalkoxy group, cycloalkylaminocarbonylalkoxy group, alkenylaminocarbonylalkoxy group, alkynylaminocarbonylalkoxy group An alkoxycarbonylalkoxycarbonylalkoxy group, an alkoxyalkoxycarbonylalkoxy group, an alkylthioalkoxycarbonylalkoxy group, Alkoxycarbonyl alkoxycarbonylalkyl thio group, alkoxycarbonyl alkoxycarbonylalkyl thio group, an alkyl thio alkoxycarbonylalkyl thio group, an alkylamino group, a dialkylamino group, alkynyl group, a cycloalkyl group, an alkylsulfonylamino group, N- alkyl -N-
Alkynylamino group, N-alkyl-N-alkoxyalkylamino group, alkoxycarbonylalkoxycarbonyl group, alkenyloxycarbonylalkoxycarbonyl group, haloalkenyloxycarbonylalkoxycarbonyl group, cycloalkylalkylthio group, alkynyloxycarbonylalkoxycarbonyl group, alkoxyalkoxy Represents a carbonylalkoxycarbonyl group or a carboxylalkoxy group, R ^{8 ′} is a hydrogen atom,
Represents a halogen atom, a hydroxyl group, an amino group or an alkoxy group. Y represents the same meaning as described above, and R ^{9 ′} represents an alkyl group, a haloalkyl group, a hydroxyalkyl group, an alkoxyalkyl group, a haloalkoxyalkyl group, an alkylthioalkyl group, an alkylsulfinylalkyl group,
It represents an alkylsulfonylalkyl group, a carboxyl group, an alkoxycarbonyl group, a haloalkoxycarbonyl group, a cycloalkyloxycarbonyl group or an alkynyloxycarbonyl group, and R ^{10 ′} represents a hydrogen atom or an alkyl group. ]. 2-pyridone derivatives represented by｝. 5. A herbicide comprising the 2-pyridone derivative according to claim 1, 2, 3, or 4 as an active ingredient.