JP2002241205A - Herbicide composition containing condensed cyclic benzoyl derivative - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an herbicide excellent in selectivity between crops and weeds, having high weed-killing activity and a wide weed-killing spectrum in a low dosage. SOLUTION: This herbicide composition contains (A) a condensed cyclic benzoyl derivative expressed by the general formula (I) [wherein, R1 to R6 are each H, a halogen, a 1-6C alkyl or haloalkyl, or the like; Q is hydroxyl, a halogen, a 1-6C alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, phenoxy, phenylsulfinyl or phenylysulfonyl, a 2-12C dialkylamino, or the like; X is a halogen atom, nitro, cyano or the like; (p) is 0-2; Z is H, a 1-6C alkyl, a 3-6C cycloalkyl or the like; (m) is 1-2; and (n) is 0-2] and/or its salt, and (B) an herbicide for weeds belonging to Gramineae and/or herbicide for broadleaf weeds/weeds belonging to Cyperaceae as active ingredients.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a herbicidal composition, and more particularly to a fused cyclic benzoyl derivative having a structure in which a 2,3-dihydrobenzothiophene or thiochroman skeleton is bonded to a cyclohexenone ring via a carbonyl group. And / or a salt thereof, and a herbicide effective for grass weeds such as flies (Poaceae) and / or a herbicide effective for broadleaf weeds and cyperaceae weeds.
The herbicidal composition of the present invention has a broad herbicidal spectrum due to the synergistic effect of the condensed cyclic benzoyl derivative and / or a salt thereof and a grass weed herbicide and / or a broadleaf weed / Cyperaceae weed herbicide. It is effective for controlling various paddy field weeds and upland field weeds, especially for paddy field weeds. It can effectively control weeds.

[0002]

2. Description of the Related Art Various herbicides have been developed so far, and have contributed to improving the productivity of agricultural crops and saving labor. However, the herbicides that have been developed so far cannot be said to have a sufficiently wide spectrum of herbicides, and the present situation is that the number of difficult-to-control weeds is increasing, and there is a need for herbicides having a broader spectrum of herbicides. In addition, there is a need for a herbicide that has a small effect on the environment, a low dose and a high herbicidal effect.

It has been reported that a herbicide containing a triketone derivative having a certain condensed cyclic benzoyl structure as an active ingredient is highly safe against field crops and exhibits excellent herbicidal activity against field weeds. ing. For example, Japanese Patent No. 2,579,663 and International Publication WO97 / 0816
The herbicide containing the compound described in JP-A No. 4 as an active ingredient has an excellent effect as a herbicide for field weeds. However, herbicides containing these compounds as active ingredients have a problem in that they do not have sufficient herbicidal effects against paddy weeds and are not sufficient in terms of safety against paddy rice.

[0004] The present inventor has conducted research on herbicides which have little phytotoxicity to cultivated crops, especially paddy rice, and can control a wide range of weeds at a low dose. First, a herbicide containing a triketone derivative as an active ingredient has been studied. (International Publication W
O00 / 20408). This triketone derivative has a structure in which a 2,3-dihydrobenzothiophene or thiochroman skeleton has 2-cyclohexene- via a carbonyl group.
It has a structure linked to the 2-position of the 1-one ring, has little phytotoxicity to cultivated crops, especially rice, can control a wide variety of weeds at a low dose, and is a herbicide component for rice. Useful.

[0005] In the paddy field, various grasses, broadleaf weeds and cyperaceae weeds such as grass weeds such as velvet, waterweed weeds such as conger, cyperaceae weeds such as fireflies and porpoises, and weeds and weeds such as urikawa. appear. Therefore, rice-weed selectivity is excellent,
There is a need for a herbicide having an excellent herbicidal activity and a broad herbicidal spectrum capable of simultaneously controlling these various kinds of weeds at a low dose without damaging the rice. Although the triketone derivative can control a wide variety of weeds, it was not always satisfactory to sufficiently control the various kinds of paddy weeds at the same time. As a compound similar to the triketone derivative, a compound of the formula (II)

[0006]

Embedded image

A compound represented by the following formula has been proposed (JP-A-6-25144). Although this compound is effective as a rice herbicide, when used alone, it is not satisfactory for controlling various kinds of paddy weeds such as grasses and broadleaf weeds at the same time.

[0008]

SUMMARY OF THE INVENTION Under such circumstances, the present invention has excellent selectivity between crops and weeds, has high herbicidal activity and a broad herbicidal spectrum, and has a variety of grasses, broadleaf weeds and cyperaceae. The purpose of the present invention is to provide a herbicide that can control a wide range of weeds, such as weeds, at a low dose, contribute to further improving the productivity of agricultural crops and save labor, and also have less impact on the environment. is there.

[0009]

Means for Solving the Problems The inventors of the present invention have conducted intensive studies to develop the above herbicides having excellent performance, and as a result, the 2,3-dihydrobenzothiophene or thiochroman skeleton is linked via a carbonyl group. 2-cyclohexene-
The combined use of a condensed cyclic benzoyl derivative having a structure bonded to the 2-position of the 1-one ring and a grass weed herbicide or broadleaf weed / Cyperaceae weed herbicide exhibits a synergistic effect, It has been found that grass activity is improved and that a broad spectrum of weeds can be controlled at very low doses without broadening the herbicidal spectrum and without damaging the crop. The present invention has been completed based on such findings.

That is, the present invention relates to (A) a compound represented by the general formula (I)

[0011]

Embedded image

[0012] wherein, R ¹ to R ⁶ are each independently a hydrogen atom, a halogen atom, an alkyl group or a haloalkyl group having 1 to 6 carbon atoms having 1 to 6 carbon atoms, from R ¹ to R ⁶ Any two selected groups may be linked to each other to form a bicyclo ring structure with the cyclohexene ring;
Is a hydroxyl group, a halogen atom, an alkoxy group having 1 to 6 carbon atoms which may have a substituent, an alkylthio group having 1 to 6 carbon atoms which may have a substituent, C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group optionally having substituent (s), phenoxy group optionally having substituent (s), even having substituent (s) A good phenylthio group, a phenylsulfinyl group which may have a substituent, a phenylsulfonyl group which may have a substituent, a dialkylamino group having 2 to 12 carbon atoms which may have a substituent, A dicycloalkylamino group having 6 to 12 carbon atoms which may have a group, an N-alkoxyalkylamino group having 2 to 12 carbon atoms which may have a substituent, and a nitrogen atom forming a cyclohexenone ring. Join, replace A 5- or 6-membered nitrogen-containing heterocyclic group which may have a malonic ester residue bonded to the cyclohexenone ring at the α-position, a β-ketoester residue bonded to the cyclohexenone ring at the α-position, α Represents a β-diketone residue or a 5- or 6-membered heterocyclic sulfide group which may have a substituent; X represents a halogen atom, a nitro group, a cyano group, R ⁸ , O
R ⁸ , SR ⁸ , SO ₂ R ⁸ or NR ⁸ R ⁹ [R ⁸ and R ⁹ each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms which may have a substituent, A cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms which may have a substituent, or an alkynyl having 2 to 6 carbon atoms which may have a substituent And a phenyl group which may have a substituent or a benzyl group which may have a substituent, which may be bonded to each other to form a ring structure]; Or 2; Z is a hydrogen atom,
An alkyl group having 1 to 6 carbon atoms which may have a substituent,
A cycloalkyl group having 3 to 6 carbon atoms which may have a substituent or -YR ⁷ [Y represents O, S, SO or SO ₂ , and R ⁷ may have a substituent Represents an alkyl group having 1 to 6 carbon atoms]; m represents 1 or 2; n represents 0, 1 or 2. And at least one compound selected from the group consisting of (B) a grass weed herbicide and a broadleaf weed / Cyperaceae weed herbicide represented by the formula (I): The present invention provides a herbicidal composition characterized by containing

[0013]

BEST MODE FOR CARRYING OUT THE INVENTION The herbicidal composition of the present invention comprises (A)
The following general formula (I)

[0014]

Embedded image

And at least one compound selected from the group consisting of (B) a herbicide for grass weeds and a herbicide for broadleaf weeds and cyperaceae weeds represented by the following general formula (I): Contains as an active ingredient.

In the general formula (I), R ^{1 to} R ⁶ are
Each independently a hydrogen atom, a halogen atom, a carbon number of 1 to
6 represents an alkyl group or a haloalkyl group having 1 to 6 carbon atoms. Any two groups in R ^{1 to} R ⁶ are bonded to each other,
A bicyclo ring structure may be formed together with the cyclohexene ring. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Examples of the alkyl group having 1 to 6 carbon atoms include a methyl group, an ethyl group, and a linear or branched propyl group or butyl group. Group, pentyl group and hexyl group. Specific examples of the haloalkyl group having 1 to 6 carbon atoms include a haloalkyl group in which part or all of the hydrogen atoms of the alkyl group are substituted with a halogen atom such as a chlorine atom, a fluorine atom, a bromine atom or an iodine atom, Chloromethyl group, difluoromethyl group,
Examples include a trichloromethyl group, a trifluoromethyl group, a 2-chloroethyl group, a 2-fluoroethyl group, a 3-chloropropyl group, and a 3-fluoropropyl group. The bicyclo ring structure formed by combining any two groups in R ^{1 to} R ⁶ with each other includes bicyclo [3.2.
1] Octane ring structure and the like. As R ^{1 to} R ⁶ , a hydrogen atom is particularly preferred.

Q represents a hydroxyl group, a halogen atom, an alkoxy group having 1 to 6 carbon atoms which may have a substituent, an alkylthio group having 1 to 6 carbon atoms which may have a substituent or a substituent. An alkylsulfinyl group having 1 to 6 carbon atoms, an alkylsulfonyl group having 1 to 6 carbon atoms which may have a substituent, a phenoxy group optionally having a substituent, Optionally substituted phenylthio group, optionally substituted phenylsulfinyl group, optionally substituted phenylsulfonyl group, optionally substituted dialkyl having 2 to 12 carbon atoms An amino group, a dicycloalkylamino group having 6 to 12 carbon atoms which may have a substituent, and a carbon atom having 2 to 1 carbon atoms which may have a substituent;
2, an N-alkoxy-N-alkylamino group, an optionally substituted 5- or 6-membered nitrogen-containing heterocyclic group bonded to the cyclohexenone ring at a nitrogen atom, a cyclohexenone ring at the α-position A malonate residue bonded to the cyclohexenone ring at the α position, α
Represents a β-diketone residue bonded to a cyclohexenone ring at the 2-position, or a 5- or 6-membered heterocyclic sulfide group which may have a substituent.

Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

The alkyl group constituting the alkoxy group having 1 to 6 carbon atoms which may have a substituent may be linear or branched, and the alkoxy group having 1 to 6 carbon atoms may be substituted. , A thiophenyl group, a furanyl group, a phenyl group and the like. Examples of the optionally substituted alkoxy group having 1 to 6 carbon atoms include a methoxy group, an ethoxy group, an isopropoxy group, a 2-chloroethoxy group, a 2-methoxyethoxy group, and 2- (thiophenyl)
And a methoxy group.

The alkyl group constituting the alkylthio group having 1 to 6 carbon atoms which may have a substituent may be linear or branched, and may be a hydroxyl group, a cyano group or an alkoxycarbonyl group. , An acyloxy group, a haloacyloxy group, a methanesulfonyl group, an acylamino group, or the like. Examples of the alkylthio group having 1 to 6 carbon atoms which may have a substituent include a methylthio group, an ethylthio group, a 2-hydroxyethylthio group,
Cyanoethylthio group, 2-ethoxycarbonylethylthio group, 2-hydroxypropylthio group, 2-acetoxyethylthio group, 2- (chloroacetoxy) ethylthio group, 2-methanesulfonylethylthio group, 2- (acetylamino) ethylthio And the like.

The alkyl group in the alkylsulfinyl group having 1 to 6 carbon atoms which may have a substituent may be linear or branched, and may be a hydroxyl group, a cyano group or an alkoxy group. It may be substituted with a carbonyl group, an acyloxy group, a haloacyloxy group, a methanesulfonyl group, an acylamino group, or the like. Examples of the alkylsulfinyl group having 1 to 6 carbon atoms which may have a substituent include, for example, a methylsulfinyl group, an ethylsulfinyl group,
-Hydroxyethylsulfinyl group, 2-cyanoethylsulfinyl group, 2-hydroxypropylsulfinyl group, 2-acetoxyethylsulfinyl group, 2- (chloroacetoxy) ethylsulfinyl group, 2-methanesulfonylethylsulfinyl group, 2- (acetylamino)
And an ethylsulfinyl group.

The alkyl group in the alkylsulfonyl group having 1 to 6 carbon atoms which may have a substituent may be linear or branched, and may be a hydroxyl group, a cyano group or an alkoxycarbonyl group. , An acyloxy group, a haloacyloxy group, a methanesulfonyl group, an acylamino group, or the like. Examples of the alkylsulfonyl group having 1 to 6 carbon atoms which may have a substituent include a methylsulfonyl group, an ethylsulfonyl group, a 2-hydroxyethylsulfonyl group, a 2-cyanoethylsulfonyl group,
2-hydroxypropylsulfonyl group, 2-acetoxyethylsulfonyl group, 2- (chloroacetoxy) ethylsulfonyl group, 2-methanesulfonylethylsulfonyl group, 2- (acetylamino) ethylsulfonyl group, 2-
(Ethoxycarbonyl) ethylsulfonyl group and the like.

Examples of the substituent of the phenoxy group, phenylthio group, phenylsulfinyl group and phenylsulfonyl group include a linear or branched alkyl group having 1 to 6 carbon atoms, a hydroxyl group and a halogen atom. Examples of the phenoxy group which may have a substituent include a phenoxy group,
A methylphenoxy group, a 4-hydroxyphenoxy group and the like; examples of a phenylthio group which may have a substituent include a phenylthio group, a 4-methylphenylthio group and a 4-hydroxyphenyl group; Examples of the phenylsulfinyl group which may have a substituent include a phenylsulfinyl group, a 4-methylphenylsulfinyl group, and a 4-hydroxyphenylsulfinyl group; and a phenylsulfonyl group which may have a substituent. Examples of the group include a phenylsulfonyl group, 4-
Examples include a methylphenylsulfonyl group and a 4-hydroxyphenylsulfonyl group.

C 2 -C 12 which may have a substituent
The alkyl group in the dialkylamino group may be linear or branched, and may be substituted. Examples of the dialkylamino group having 2 to 12 carbon atoms which may have a substituent include a dimethylamino group, a diethylamino group, and a diisopropylamino group.

C 6 -C 12 which may have a substituent
The cycloalkyl group in the dicycloalkylamino group of
It may be substituted. Examples of the optionally substituted dicycloalkylamino group having 6 to 12 carbon atoms include a dicyclohexylamino group.

C 2 -C 12 which may have a substituent
The alkoxy group in the N-alkoxy-N-alkylamino group is a linear or branched alkoxy group having 1 to 6 carbon atoms, and the alkyl group is a linear or branched alkyl group having 1 to 6 carbon atoms. Alkoxy and / or alkyl groups may be substituted. 2 to 2 carbon atoms which may have a substituent
Examples of the 12 N-alkoxy-N-alkylamino groups include an N-methoxy-N-methylamino group.

Examples of the optionally substituted 5- or 6-membered nitrogen-containing heterocyclic group bonded to the cyclohexenone ring by a nitrogen atom include a pyrrolidine residue, a piperidine residue, a morpholine residue, Pyrazole residue, 3-methylpyrazole residue, 1,2,4-triazole residue, 4,5-
And a dihydropyrazole residue.

Examples of the malonic ester residue bonded to the cyclohexenone ring at the α-position include a dimethyl malonate residue,
Examples of β-ketoester residues that are bonded to the cyclohexenone ring at the α-position include diethyl malonate residues; methyl acetoacetate residues and ethyl acetoacetate residues; bonded to the cyclohexenone ring at the α-position Examples of the β-diketone residue include an acetylacetone residue and a 1,3-cyclohexanedione residue.

Examples of the 5- or 6-membered heterocyclic sulfide group which may have a substituent include a 2-pyridinylthio group, a 2-pyrimidinylthio group, a (4-methylpyrimidin-2-yl) thio group, (4,6-dimethylpyrimidin-2-yl) thio group, 2-thiophenylthio group, (1,
3-thiazol-2-yl) thio group, (2-methylfuran-3-yl) thio group, (1-methylimidazole-2)
—Yl) thio group and the like.

Q represents a hydroxyl group, a chlorine atom, a bromine atom, an optionally substituted alkylthio group having 1 to 6 carbon atoms and a nitrogen atom, which are bonded to the cyclohexenone ring;
A 5-membered nitrogen-containing heterocyclic group which may have a substituent is preferable.

X is a halogen atom, a nitro group, a cyano group,
R ⁸ , OR ⁸ , SR ⁸ , SO ₂ R ⁸ or NR ⁸ R ⁹ are shown. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. R ⁸ and R ⁹ each independently represent an alkyl group having 1 to 6 carbon atoms which may have a substituent, a cycloalkyl group having 3 to 6 carbon atoms which may have a substituent, An alkenyl group having 2 to 6 carbon atoms which may have, 2 to 6 carbon atoms which may have a substituent
Represents an alkynyl group, a phenyl group which may have a substituent or a benzyl group which may have a substituent. Examples of the substituent include a halogen atom such as chlorine and fluorine, an alkoxy group having 1 to 6 carbon atoms such as methoxy and ethoxy, and an alkyl group having 1 to 6 carbon atoms such as methyl and ethyl. The alkyl group having 1 to 6 carbon atoms which may have a substituent may be linear or branched, for example, methyl, ethyl, isopropyl, trichloromethyl, difluoromethyl, trifluoromethyl Group, methoxymethyl group and the like. Examples of the cycloalkyl group having 3 to 6 carbon atoms which may have a substituent include a cyclopropyl group and a cyclohexyl group. The alkenyl group having 2 to 6 carbon atoms which may have a substituent may be linear or branched, for example, a vinyl group,
Examples include an allyl group, a 1-propenyl group, and a 1-ethoxyethenyl group. 2 to 2 carbon atoms which may have a substituent
The alkynyl group of No. 6 may be linear or branched, and examples thereof include an ethynyl group, a 1-propynyl group, and a 2-propynyl group. Examples of the phenyl group which may have a substituent include a phenyl group and a 4-methylphenyl group. Examples of the benzyl group which may have a substituent include a benzyl group and an α-methylbenzyl group. In NR ⁸ R ⁹ , R ⁸
And R ⁹ may be bonded to each other to form a ring structure to form a pyrrolidine ring, a hyperidine ring, a morpholine ring, or the like. X is preferably a chlorine atom, a bromine atom, a nitro group, a cyano group, a methyl group, an ethyl group, a trifluoromethyl group and a methoxymethyl group.

P is 0, 1 or 2, preferably 1 or 2. When p is 2, two Xs may be the same or different.

Z is a hydrogen atom and may have a substituent
An alkyl group having 1 to 6 carbon atoms, which may have a substituent
C3-C6 cycloalkyl group or -YR⁷Shows
You. The alkyl group having 1 to 6 carbon atoms may be linear or branched.
It may be. C1-C6 alkyl group and carbon
The cycloalkyl group of the number 3 to 6 is a halo such as chlorine and fluorine.
C1-C6 alkoxy groups such as gen atoms and methoxy
It may be replaced by, for example. May have a substituent
Examples of the alkyl group having 1 to 6 carbon atoms include methyl
Group, ethyl group, isopropyl group, trichloromethyl group,
Difluoromethyl group, trifluoromethyl group, methoxy
And a methyl group. May have a substituent
As the cycloalkyl group having 3 to 6 carbon atoms, for example,
Examples thereof include a chloropropyl group and a cyclohexyl group.
Y is O, S, SO or SO_TwoAnd R⁷Has 1 to 6 carbon atoms
Alkoxy group, oxo group, alkoxy having 1 to 6 carbon atoms
Imino group, hydroxyimino group, alcohol having 2 to 6 carbon atoms
An optionally substituted carbon such as a xycarbonyl group
It represents a linear or branched alkyl group of the formulas 1 to 6. R ⁷When
For example, methyl group, ethyl group, isopropyl
Group, propyl group, 2-methoxyethyl group, 2,2-dimethyl
Toxylethyl group, 2-oxoethyl group, 2-methoxyyl
Minoethyl group, 2-hydroxyiminoethyl group, methoxy
Cicarbonylmethyl group and the like; methyl group, ethyl
Isopropyl, 2-methoxyethyl, 2-methyl
Toxiliminoethyl group and methoxycarbonylmethyl group
Is preferred. As Z, particularly a hydrogen atom, a methyl group,-
SR⁷And -SO_Two-R⁷Is preferred.

M is 1 or 2, preferably 1, and n is 0, 1, or 2, preferably 2.

When Q is a hydroxyl group, the condensed cyclic benzoyl derivative represented by the general formula (I) can have a tautomer structure as shown below. Cyclic benzoyl derivatives include all of these isomers and mixtures thereof.

[0036]

Embedded image [Wherein, R ^{1 to} R ⁶ , X, p, Z, m and n are the same as above. ]

When R ¹ or R ⁶ is a hydrogen atom, the condensed cyclic benzoyl derivative represented by the general formula (I) can have a tautomer structure as shown below. However, the fused cyclic benzoyl derivative according to the present invention includes all of these isomers and a mixture thereof.

[0038]

Embedded image [Wherein, R ^{1 to} R ⁶ , Q, X, p, Z, m and n are the same as above. ]

The fused cyclic benzoyl derivative represented by the above general formula (I) is described, for example, in WO99 / 33820.
WO00 / 20408, WO00 / 69853, and the method shown below.

(1) When Q is a group Q 'bonded to a carbon atom: The chloro compound (III) is converted to a compound (H
The condensed cyclic benzoyl derivative represented by the general formula (I ') can be obtained by reacting with an alkali metal salt of Q'), for example, NaQ '.

[0041]

Embedded image (In the formula, R ^{1 to} R ⁶ , X, Z, m, n, and p are the same as described above.)

In this reaction, the compound (HQ ') having active hydrogen is converted to a salt (NaQ') using an equimolar amount or more of an alkali metal reagent such as sodium hydride and reacted with the chloro compound (III). As a reaction solvent, an inert solvent such as benzene and tetrahydrofuran is suitable. In carrying out this reaction, stirring may be performed at a temperature between room temperature and the boiling point of the solvent until the reaction is completed.

(2) When m is 1, n is 2, and Z is -YR ⁷ (i) The carboxylic acid (IV) obtained by the method described in WO 00/20408 is converted into an alcohol ( R
OH) to give the ester (V).

[0044]

Embedded image (In the formula, R represents a lower alkyl group, and X and p are the same as described above.)

In this reaction, a catalytic amount of sulfuric acid, p-
A protic acid such as toluenesulfonic acid is used. The alcohol is preferably methanol or ethanol, and is used in equimolar or more. As a reaction solvent, an inert solvent such as benzene or toluene can be used or can be used without a solvent.
In carrying out this reaction, stirring may be carried out at a temperature between room temperature and the boiling point of the solvent until the reaction is completed while removing water produced by the reaction.

(Ii) The ester (V) is reacted with a halogenating agent (D ^* ) to obtain a halide (VI).

[0047]

Embedded image (In the formula, D ^* represents a halogenating agent, D represents a halogen atom, and R, X and p are the same as described above.)

In this reaction, N-bromosuccinimide (NBS) is used in an inert solvent such as carbon tetrachloride.
Is used in an equimolar amount or more. As a radical generation source, azobisisobutyronitrile (AIB
N) and the like are used in catalytic amounts. When performing this reaction, stirring may be performed until the reaction is completed at the boiling point of the solvent.

(Iii) The halogenide (VI) is dehydrohalogenated to give benzothiophene (VII).

[0050]

Embedded image (In the formula, D, R, X and p are the same as described above.)

In this reaction, a base such as triethylamine is used in an inert solvent such as methylene chloride in an equimolar amount or more. When performing this reaction, stirring may be carried out at 0 ° C. to the boiling point of the solvent until the reaction is completed. (Iv) According to the following reaction formula, a substituent -YR ⁷ is introduced into the 2-position of benzothiophene (VII) to obtain a compound (VIII).

[0052]

Embedded image (In the formula, R, R ⁷ , X, Y and p are the same as described above.)

In this reaction, a two-layer system of an inert solvent such as methylene chloride and water and a nucleophile such as a sodium salt of methanethiol are used in equimolar amounts or more. As a layer transfer catalyst, a catalytic amount of tetrabutylammonium bromide (TBAB) or the like is used. When performing this reaction, stirring may be carried out from room temperature to the boiling point of the solvent until the reaction is completed.

(V) The compound (VIII) is hydrolyzed to obtain a carboxylic acid (IX).

[0055]

Embedded image (In the formula, R, R ⁷ , X and p are the same as described above.)

In this reaction, a mixed solvent of water and a protic solvent such as methanol or ethanol, or, if necessary, an inert solvent such as methylene chloride is further added to the mixture to form a mixture such as sodium hydroxide or lithium hydroxide. The base is used in equimolar or more. When performing this reaction, stirring may be carried out at 0 ° C. to the boiling point of the solvent until the reaction is completed.

(Vi) A condensed cyclic compound represented by the general formula (I) (where Z = -YR ⁷ ) from a carboxylic acid (IX) by a method described in International Publication WO00 / 20408 or the like. Benzoyl derivatives can be obtained.

The condensed cyclic benzoyl derivative represented by the general formula (I) obtained as described above can be converted to a salt by treating with an acid or a base. The fused cyclic benzoyl derivative used in the present invention also includes these salts. Examples of the acid that forms a salt include inorganic acids such as hydrochloric acid, hydroiodic acid, hydrobromic acid, hydrofluoric acid, sulfuric acid, nitric acid, and phosphoric acid, and acetic acid, methanesulfonic acid, and toluenesulfonic acid. Organic acids are used. Examples of the base include organic bases such as amines and anilines, and inorganic bases such as ammonia, sodium compounds, and potassium compounds. Examples of the amines include alkylamines such as monoalkylamine, dialkylamine, and trialkylamine. Examples of the anilines include anilines, alkyl anilines such as monoalkyl anilines and dialkyl anilines. Examples of the sodium compound include sodium hydroxide and sodium carbonate, and examples of the potassium compound include potassium hydroxide and potassium carbonate.

In the herbicidal composition of the present invention, the condensed cyclic benzoyl derivative represented by the above general formula (I) and a salt thereof may be used alone or in combination of two or more.

The combined use of the condensed cyclic benzoyl derivative of the component (A) and / or a salt thereof and the herbicide for the weed and / or the broadleaf weed / Cyperaceae weed of the component (B), The herbicidal compositions of the present invention exhibit a synergistically improved herbicidal activity and a broad herbicidal spectrum. As the component (B), conventionally known grass weed herbicides and / or broadleaf weeds shown in Tables 1 and 2 below.
Cyperaceae weed herbicides are used.

[0061]

[Table 1]

[0062]

[Table 2]

[0063]

[Table 3]

Among the compounds shown in Table 1, particularly preferred grass weed herbicides are 3- (4-chloro-5-cyclopentyloxy-2-fluorophenyl) -5-isopropylidene-1,3- Oxazolidine-2,4-dione, 2-chloro-2 ', 6'-diethyl-N- (butoxymethyl) acetanilide, 2-chloro-2', 6'-
Diethyl-N- (2-propoxyethyl) acetanilide, 2-chloro-N-[(3-methoxy-2-thienyl) methyl] -2 ', 6'-dimethylacetanilide,
exo-1-methyl-4- (1-methylethyl) -2-
(2-Methylphenylmethoxy) -7-oxabicyclo [2.2.1] heptane, S, S'-dimethyl-2-difluoromethyl-4-isobutyl-6-trifluoromethylpyridine-3,5-dicarbo Thioate, S- (4
-Chlorobenzyl) -N, N-diethylthiocarbamate, O-3-tert-butylphenyl-6-methoxy-2-pyridyl (methyl) thiocarbamate, S-ethylhexahydro-1H-azepine-1-carbothioate , 2-benzothiazol-2-yloxy-N-methylacetanilide, 2 ', 3'-dichloro-4-ethoxymethoxybenzanilide, N, N-diethyl-3-mesitylsulfonyl-1H-1,2,4 -Triazole-1
-Carboxamide, 2- [2- (3-chlorophenyl)
-2,3-epoxypropyl] -2-ethylindane-
1,3-dione, 3- [1- (3,5-dichlorophenyl) -1-methylethyl] -2,3-dihydro-6-methyl-5-phenyl-4H-1,3-oxazine-4-
On, 4- (2-chlorophenyl) -N-cyclohexyl-4,5-dihydro-N-ethyl-5-oxo-1H
-Tetrazole-1-carboxamide, butyl (R)
-2- [4- (4-cyano-2-fluorophenoxy)
Phenoxy] propionate, methyl 2- (4,6-
Dimethoxypyrimidin-2-yloxy) -6- (1-
Methoxyiminoethyl) benzoate, 7- (4,6-
Dimethoxypyrimidin-2-ylsulfanyl) -3-
Methyl-3H-isobenzofuran-1-one and 3 ',
4'-dichloropropionanilide.

[0065]

[Table 4]

[0066]

[Table 5]

[0067]

[Table 6]

Among the compounds shown in Table 2, a particularly preferred herbicide for broadleaf weeds and cyperaceae weeds is methyl.
α- (4,6-dimethoxypyrimidin-2-ylcarbamoylsulfamoyl) -o-triate, 1- (4
6-dimethoxypyrimidin-2-yl) -3- [1-methyl-4- (2-methyl-2H-tetrazol-5-yl) pyrazol-5-ylsulfonyl] urea, ethyl (4,6-dimethoxypyrimidine- 2-ylcarbamoylsulfamoyl) -1-methylpyrazole-4-carboxylate, 1- (2-chloroimidazo [1,2-
α] pyridin-3-ylsulfonyl-3- (4,6-dimethoxypyrimidin-2-yl) urea, 1- [2-
(Cyclopropylcarbonyl) anilinosulfonyl]-
3- (4,6-dimethoxypyrimidin-2-yl) urea, 4- (2,4-dichlorobenzoyl) -1,3-dimethyl-5-pyrazolyl-p-toluenesulfonate,
2- [4- (2,4-dichlorobenzoyl) -1,3-
Dimethylpyrazol-5-yloxy] acetophenone, 2- [4- (2,4-dichloro-m-toluoyl)
-1,3-dimethylpyrazol-5-yloxy]-
4'-methylacetophenone, (RS) -2- (2,4
-Dichloro-m-tolyloxy) propionanilide,
Ethyl 4- (2-methyl-4-chlorophenoxy) butyrate, S-ethyl-4-chloro-2-methylhexiothioacetate, 3-isopropyl-2,1,3-benzothiadiazinone- (4)- 2,2-dioxide sodium salt, 2-methylthio-4,6-bis (ethylamino)-
s-triazine, 2-methylthio-4-ethylamino-
6- (1,2-dimethylpropylamino) -s-triazine and 2-amino-3-chloro-1,4-naphthoquinone.

The grass weed herbicide and the broadleaf weed / Cyperaceae weed herbicide may be used in combination, or each may be used independently, or two or more may be used in combination.

The mixing ratio of the components (A) and (B)
It is appropriately selected according to conditions such as the type of crop, the type and amount of weeds to be controlled, and the climate, but is preferably 100: 1 to 1: 500, more preferably 10: 1 to 1 by weight.
The range is 1:50.

The herbicidal composition of the present invention comprises the condensed cyclic benzoyl derivative represented by the above general formula (I) and / or a salt thereof as the component (A), and the herbicide and / or broadleaf for grasses and weeds described above. It contains a herbicide for weeds and cyperaceae as a component (B). Hereinafter, the component (A) and the component (B)
A mixture with a component may be referred to as a mixed active component. The mixed active ingredient can be mixed with a liquid carrier such as a solvent or a solid carrier such as mineral fine powder, and formulated into a wettable powder, emulsion, powder or granule for use. Further, in formulating the herbicidal composition, a surfactant may be added to impart emulsifiability, dispersibility, spreadability and the like to the composition.

When the herbicidal composition of the present invention is used in the form of a wettable powder, usually 5 to 55% by weight of the mixed active ingredient, 40 to 93% by weight of the solid carrier and 2 to 5% by weight of the surfactant are used. % Of the composition may be prepared and used for weeding. When the herbicidal composition of the present invention is used in the form of an emulsion, usually 10 to 50% by weight of the mixed active ingredient, 35 to 85% by weight of the solvent and 5 to 15% of the surfactant are used.
What is necessary is just to prepare the composition mix | blended by the ratio of weight%, and to use this for weeding. When the herbicidal composition of the present invention is used in the form of a powder, usually 1 to 15% by weight of the mixed active ingredient, 80 to 97% by weight of the solid carrier and 2% of the surfactant are used.
What is necessary is just to prepare and use the composition mix | blended by the ratio of 5 weight%. Further, when the herbicidal composition of the present invention is used in the form of granules, usually 1 to 15% by weight of the mixed active ingredient, 80 to 97% by weight of the solid carrier and 2% by weight of the surfactant are used.
What was formed into granules of the composition blended at a ratio of 〜5% by weight may be used for weeding.

Examples of the solid carrier used here include oxides such as diatomaceous earth and slaked lime, phosphates such as apatite, sulfates such as gypsum, talc, biloferrite, clay, kaolin, bentonite, acid clay, Suitable examples include fine powders of mineral substances such as white carbon, quartz powder, and silica stone powder. Examples of the solvent include benzene, aromatic hydrocarbons such as toluene or xylene, o-chlorotoluene, chlorinated hydrocarbons such as trichloroethane or trichloroethylene, cycloxanol, amyl alcohol, alcohols such as ethylene glycol, isophorone, Organic solvents such as cyclohexanone, ketones such as cyclohexenylcyclohexanone, ethers such as butyl cellosolve, diethyl ether and methyl ethyl ether, isopropyl acetate, benzyl acetate, esters such as methyl phthalate, amides such as dimethylformamide, and mixtures thereof are preferable. Are listed.

Further, as the surfactant, any of anionic, nonionic, cationic and amphoteric surfactants such as amino acids and betaine can be used.

The herbicidal composition of the present invention requires, in addition to the components (A) and (B), components having other herbicidal activities, insecticides, fungicides, plant growth regulators, fertilizers, and the like. It can also be contained as needed.

The herbicidal composition of the present invention is applied to a weed or its habitat before or after germination of the weed. The application means varies depending on the type of cultivated plant and the use environment, but for example, methods such as spraying, spraying, watering, and water injection can be adopted. The application amount of the herbicide of the present invention is determined in consideration of various conditions such as the form of the preparation, the method of spraying, the type and amount of the weed, and the growth status. Usually, 0.01 to 10 kg / ha, preferably 0.05 to 10 kg / ha, as a mixed active ingredient.
It is 5 kg / ha, and those skilled in the art can easily determine an effective amount for obtaining a necessary herbicidal effect.

The cultivated plants protected from the damage of weeds by the herbicidal composition of the present invention include, for example, rice, wheat,
In addition to grasses such as barley, corn, oat, and sorghum, broadleaf crops such as soybean, cotton, beet, sunflower, and rapeseed, vegetables such as fruit trees, fruit and root vegetables, and leafy vegetables, and lawns are included.

The weeds to be controlled by the herbicidal composition of the present invention include various paddy field weeds and field weeds.
As paddy field weeds, the Japanese mosquito (Arisma ca
naliculatum) and the Japanese mosquito (Sagitta)
ria trifolia), Urikawa (Sagitt)
aria pygmaea)
smateaceae) Weed, Cyperus (Cyper)
us diffformis), Oyster frog (Type)
rus serotinus, firefly (Scirp)
us juncoides), Krogwai (Eleoc)
hares kuroguwai, Cyperaceae weed, Azena (Linde)
rnia pyxidaria), Scrophulariaceae weeds such as Rnia pyxidaria, Pontenderiaceae weeds such as Monochoria vaginalis, and Potamostigon weed.
nctus, etc. (Potamoget)
onaceae) weed, stag beetle (Rotala i)
lycaaceae (Lythraceae)
Weeds, Echinochloa crus
-Galli) and other gramineae (Gr.)
amineae) Weeds and the like.

As field weeds, dogwood (Sol)
anum nigrum), Korean morning glory (Da)
Solanaceae (So) such as Tura stramonium
lanaceae, weed, strawberry (Abutilon)
theophrasti), American deer (Si)
Malvaceae (Malvac) such as da spinosa
eae) weeds, Malva morning glory (Ipomoea pu)
rpurea) and Convolvulaceae (Convolvul)
aceae) Weed, Amaranthus
lividus and other Amaranthaceae (Amaranthac)
eae) Weed, Xanthium tru
marium), ragweed (Ambrosia art)
emisfolia, Galix (Galins)
ogaciliata), and thistle (Cir)
sium arvense)
io Vulgaris), Himejiyon (Eriger)
on Asteraceae (Composite)
e) Weeds, Rorippa indic
a), Sinapis arvensi
s), Nazuna (Capsella bursa-pas)
toris) and other Brassicaceae (Brassicace)
ae) Weeds, Polygonumbulum (Polygonumbulum)
ei), buckwheat (Polygonum convo)
lvulus) and Polygonacea (Polygonacea)
e) Weeds, purslane (Portulaca oler)
acea), such as Portulacac (Portulacac)
eae) Weed, Shiroza (Chenopodial al)
bum), core kaza (Chenopodium fic)
iomium), Kochia scopa
ria) and other Chenopodiaceae (Chenopodiacea)
e) Weeds, chickweed (Stellaria media)
(Caryophyllaceae) weeds, eg, Veronica persi
ca) and other Scrophulari (Scrophulari)
aceae) Weeds, communis (Commelina c)
ommunis) and communis (Commelin)
aceae) Weeds, hens (Lamium amp)
lexicaule), Himeodonishikisou (Euph)
orbia supina), Echinacea (Eup)
Euphorbiaceae weeds, such as horbia maculata, weeds, Galium spurium, Galium aparine, Rubi
rubiaceae (Rubiacea)
e) Weeds, Vigroceae weeds such as violets (Viola arvensis), Sesbania exaltata, Cassia obtusifolia, and other weeds of the broadleaf grasses of the leguminosae (Leguminosae sorghum), such as weed;
r), Panicum dichoto (Panicum dichoto)
miflorum), Johnsongrass (Sorghu)
mhaepense) and Echinochl.
oa crus-galli), crabgrass (Digit)
aria adscendes, oats (Ave)
na fatua), Ohishiba (Eleusine i)
ndica), Enokorogosa (Setaria vir)
idis) or sparrow-nosed paw (Alopecu)
rus aequalis) and other grass weeds (Gra
minaceous weeds);
yperus rotundus, Cyperus e
sclerentus) and other Cyperaceae weeds (Cy
peripheral weeds).

[0080]

EXAMPLES Next, the present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples. In the following examples, compounds A-1 to A-26 shown in Table 3 were used as components (A), and compounds B-1 to B-35 shown in Table 4 were used as components (B). Compounds B-1 to B-35 were prepared by the methods shown in Table 5.

[0081]

[Table 7]

[0082]

[Table 8]

[0083]

[Table 9]

[0084]

[Table 10]

[0085]

[Table 11]

[0086]

[Table 12]

[0087]

[Table 13]

Examples 1 to 910 [1] Preparation of herbicide composition 57 parts by weight of talc, 40 parts by weight of bentonite, and 3 parts by weight of sodium alkylbenzenesulfonate as a surfactant were uniformly ground and mixed to prepare a wettable powder. Was obtained. To 90 parts by weight of the obtained wettable powder carrier, a condensed cyclic benzoyl derivative (one type of compounds A-1 to A-26) of the component (A),
Alternatively, 10 parts by weight of the herbicide (one of the compounds B-1 to B-35) of the component (B) is mixed and pulverized uniformly to obtain a wettable powder containing the component (A) and water containing the component (B) A sum was obtained. Next, after the component (A) -containing wettable powder and the component (B) -containing wettable powder are each diluted with water, they are mixed at a predetermined ratio,
A herbicidal composition was prepared.

[2] Herbicidal test A paddy field soil was filled in a 1/2000 arel wagnal pot, and seeds of red snapper, scallop, firefly, serrata, and urikawa were sown on the surface layer, and rice seedlings at the 2.5 leaf stage were transplanted. did. In addition, the flooding depth was 3 cm. The pot was grown in a greenhouse at 20 to 25 [deg.] C., and on the 15th day after transplanting the paddy rice, a predetermined amount of the herbicidal composition (wettable powder) prepared in [1] above was added and treated. Twenty days after the chemical treatment, the herbicidal rate, the herbicidal effect and the phytotoxicity of rice were determined as follows. The results are shown in Table 6.

(1) Weed kill rate (%) The above-ground fresh grass weight in the chemical treatment area and the above-ground fresh grass weight in the non-treated area were measured. The weed kill ratio was calculated from the formula: (grass weight) / (aboveground raw grass weight of untreated area) x 100.

(2) Herbicidal effect The herbicidal effect was determined according to the following criteria. Degree of herbicidal effect Herbicidal rate 0 Less than 5% (almost no effect) 1 5% or more to less than 20% 2 20% or more to less than 40% 3 40% or more to less than 70% 4 70% or more to less than 90% 5 90% (Almost completely withered)

(3) Damage to Paddy Rice Damage to paddy rice was determined according to the following criteria. Degree of phytotoxicity 0: No phytotoxicity to crops was observed. 1: Little phytotoxicity to crops was observed. 2: Some phytotoxicity to crops was observed. 3: Some phytotoxicity was observed to crops. : Crops almost die

Comparative Examples 1 to 61 The wettable powder containing the component (A) and the wettable powder containing the component (B) obtained in the same manner as in the above example were diluted with water, respectively, to give the components (A) and (B). Comparative herbicidal compositions containing only one of the components were prepared. A herbicidal test was performed in the same manner as in the above example except that the comparative herbicidal composition was used. The results are shown in Table 7.

[0094]

[Table 14]

[0095]

[Table 15]

[0096]

[Table 16]

[0097]

[Table 17]

[0098]

[Table 18]

[0099]

[Table 19]

[0100]

[Table 20]

[0101]

[Table 21]

[0102]

[Table 22]

[0103]

[Table 23]

[0104]

[Table 24]

[0105]

[Table 25]

[0106]

[Table 26]

[0107]

[Table 27]

[0108]

[Table 28]

[0109]

[Table 29]

[0110]

[Table 30]

[0111]

[Table 31]

[0112]

[Table 32]

[0113]

[Table 33]

[0114]

[Table 34]

[0115]

[Table 35]

[0116]

[Table 36]

[0117]

[Table 37]

[0118]

[Table 38]

[0119]

[Table 39]

[0120]

[Table 40]

[0121]

[Table 41]

[0122]

The herbicidal composition of the present invention comprises a condensed cyclic benzoyl derivative having a structure in which a 2,3-dihydrobenzothiophene or thiochroman skeleton is bonded to a cyclohexenone ring via a carbonyl group, and / or a salt thereof. A herbicide for grass weeds and / or herbicides for broadleaf weeds and cyperaceae weeds, due to their synergistic effect,
It has a high herbicidal activity and a broad herbicidal spectrum. A wide range of weeds such as grass weeds, cyperaceae weeds, and broadleaf weeds can be controlled at low doses, contributing to improved crop productivity and labor savings in weeding operations. INDUSTRIAL APPLICABILITY The herbicidal composition of the present invention is particularly effective as a herbicide for paddy rice, because it has little phytotoxicity to paddy rice.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat ゛ (Reference) A01N 43/12 A01N 43/12 B 43/20 43/20 43/38 43/38 43/54 43/54 C 43/56 43/56 DC 43/70 43/70 43/72 43/72 43/78 101 43/78 101 43/86 101 43/86 101 47/12 47/12 Z 47/16 47/16 B 47/36 101 47/36 101E 57/30 57/30 D

Claims (10)

[Claims] (A) General formula (I) [Wherein, R ^{1 to} R ⁶ each independently represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 6 carbon atoms or 1 to 6 carbon atoms.
And any two groups selected from R ^{1 to} R ⁶ may be bonded to each other to form a bicyclo ring structure together with a cyclohexene ring; Q is a hydroxyl group, a halogen atom, a substituent An alkoxy group having 1 to 6 carbon atoms which may have a substituent, 1 to 6 carbon atoms optionally having a substituent
An alkylthio group having 1 carbon atoms which may have a substituent
To 6 alkylsulfinyl groups, an optionally substituted alkylsulfonyl group having 1 to 6 carbon atoms, a phenoxy group optionally having a substituent, a phenylthio group optionally having a substituent, A phenylsulfinyl group which may have a substituent, a phenylsulfonyl group which may have a substituent, and C 2 to C 12 which may have a substituent
A dialkylamino group having 6 to 12 carbon atoms which may have a substituent, an N-alkoxyalkylamino group having 2 to 12 carbon atoms which may have a substituent, and a nitrogen atom Bonds to the cyclohexenone ring with
A 5- or 6-membered nitrogen-containing heterocyclic group which may have a substituent, a malonic ester residue bonded to the cyclohexenone ring at the α-position, a β-ketoester residue bonded to the cyclohexenone ring at the α-position X represents a halogen atom, a nitro group, a cyano group, a β-diketone residue bonded to a cyclohexenone ring at the α-position, or a 5- or 6-membered heterocyclic sulfide group which may have a substituent. R ⁸ , OR ⁸ , SR ⁸ , SO ₂
R ⁸ or NR ⁸ R ⁹ [R ⁸ and R ⁹ are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms which may have a substituent, or a carbon number which may have a substituent; A cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms which may have a substituent, and a carbon atom having 2 to 6 carbon atoms which may have a substituent
An alkynyl group, a phenyl group which may have a substituent, or a benzyl group which may have a substituent,
P may represent 0, 1 or 2; Z represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms which may have a substituent, A cycloalkyl group having 3 to 6 carbon atoms which may have a group or -YR
^{7 represents} [Y represents O, S, SO or SO ₂ , R ⁷ represents an alkyl group having 1 to 6 carbon atoms which may have a substituent]; m represents 1 or 2; Represents 0, 1 or 2. And (B) a herbicide for grass weeds and broadleaf weeds.
A herbicidal composition comprising, as an active ingredient, at least one compound selected from the group consisting of cyperaceae weed herbicides. 2. The herbicide according to claim 1, comprising (A) the condensed cyclic benzoyl derivative and / or a salt thereof, and (B) the herbicide for grasses as an active ingredient. Composition. 3. The method according to claim 1, further comprising (A) the condensed cyclic benzoyl derivative and / or a salt thereof, and (B) the herbicide for broadleaf weeds and Cyperaceae weeds as active ingredients. Herbicide composition. 4. The grass weed herbicide according to claim 1, wherein said herbicide is methyl 5
-(2,4-dichlorophenoxy) -2-nitrobenzoate, 3- (4-chloro-5-cyclopentyloxy-2-fluorophenyl) -5-isopropylidene-
1,3-oxazolidine-2,4-dione, 3- [2,
4-dichloro-5- (2-propynyloxy) phenyl] -5- (1,1-dimethylethyl) -1,3,4-
Oxadiazol-2 (3H) -one, O-ethyl-O
-(3-methyl-6-nitrophenyl) -sec-butylphosphoramidothioate, O, O-diisopropyl-2- (benzenesulfonamido) ethyldithiophosphate, 2-chloro-2 ', 6'-diethyl- N- (butoxymethyl) acetanilide, 2-chloro-2 ',
6'-diethyl-N- (2-propoxyethyl) acetanilide, 2-chloro-N-[(3-methoxy-2-thienyl) methyl] -2 ', 6'-dimethylacetanilide, exo-1-methyl-4 -(1-methylethyl)-
2- (2-methylphenylmethoxy) -7-oxabicyclo [2.2.1] heptane, S, S'-dimethyl-2
-Difluoromethyl-4-isobutyl-6-trifluoromethylpyridine-3,5-dicarbothioate, S-
(4-chlorobenzyl) -N, N-diethylthiocarbamate, S- (α, α-dimethylbenzyl) piperidine-1-carbothioate, O-3-tert-butylphenyl-6-methoxy-2-pyridyl ( Methyl) thiocarbamate, S-benzyl-N-ethyl-N- (1,2
-Dimethylpropyl) thiocarbamate, S-ethylhexahydro-1H-azepine-1-carbothioate,
2-benzothiazol-2-yloxy-N-methylacetanilide, 2 ', 3'-dichloro-4-ethoxymethoxybenzanilide, N, N-diethyl-3-mesitylsulfonyl-1H-1,2,4- Triazole-1-carboxamide, 2- [2- (3-chlorophenyl)-
2,3-epoxypropyl] -2-ethylindane-
1,3-dione, 3- [1- (3,5-dichlorophenyl) -1-methylethyl] -2,3-dihydro-6-methyl-5-phenyl-4H-1,3-oxazine-4-
On, 4- (2-chlorophenyl) -N-cyclohexyl-4,5-dihydro-N-ethyl-5-oxo-1H
-Tetrazole-1-carboxamide, S- [N- (4
-Chlorophenyl) -N-isopropylcarbamoylmethyl] -O, O-dimethyldithiophosphate, butyl (R) -2- [4- (4-cyano-2-fluorophenoxy) phenoxy] propionate, methyl 2-
(4,6-dimethoxypyrimidin-2-yloxy)-
6- (1-methoxyiminoethyl) benzoate, 7-
(4,6-dimethoxypyrimidin-2-ylsulfanyl) -3-methyl-3H-isobenzofuran-1-one, sodium 2,6-bis (4,6-dimethoxypyrimidin-2-yloxy) benzoate and 3 ′,
The herbicidal composition according to any one of claims 1 to 3, which is at least one compound selected from the group consisting of 4'-dichloropropionanilide. 5. The herbicide for broadleaf weeds and cyperaceae weeds is methyl α- (4,6-dimethoxypyrimidin-2-ylcarbamoylsulfamoyl) -o-triate, 1- (4,6-dimethoxypyrimidine). -2-yl) -3- [1-methyl-4- (2-methyl-2H-tetrazol-5-yl) pyrazol-5-ylsulfonyl] urea, ethyl (4,6-dimethoxypyrimidin-2-ylcarbamoyl Sulfamoyl) -1-methylpyrazole-4-carboxylate, 1- (2-chloroimidazo [1,2-α] pyridin-3-ylsulfonyl-3- (4,6-dimethoxypyrimidin-2-yl) Urea, 1- [2- (cyclopropylcarbonyl) anilinosulfonyl] -3- (4,6-dimethoxypyrimidin-2-yl) urea, 3- (4,6-dimethoxy-1,
3,5-triazin-2-yl-1- [2- (2-methoxyethoxy) phenylsulfonyl] urea, 3-
(4,6-dimethoxypyrimidin-2-yl-1- (2
-Ethoxyphenoxysulfonyl) urea, (RS)-
2-bromo-N- (α, α-dimethylbenzyl) -3,
3-dimethylbutylamide, 1- (α, α-dimethylbenzyl) -3- (p-tolyl) urea, 1- (2-chlorobenzyl) -3- (α, α-dimethylbenzyl) urea, 2,3 -Dihydro-3,3-dimethyl-5-benzofuranylethanesulfonate, 3- (2-chloro-4-
Methylsulfonylbenzoyl) -2-phenylthiobicyclo [3.2.1] oct-2-en-4-one, 4-
(2,4-dichlorobenzoyl) -1,3-dimethyl-
5-pyrazolyl-p-toluenesulfonate, 2- [4
-(2,4-dichlorobenzoyl) -1,3-dimethylpyrazol-5-yloxy] acetophenone, 2-
[4- (2,4-dichloro-m-toluoyl) -1,3
-Dimethylpyrazol-5-yloxy] -4'-methylacetophenone, 2- (2-naphthyloxy) propionanilide, (RS) -2- (2,4-dichloro-m
-Tolyloxy) propionanilide, ethyl 4- (2-methyl-4-chlorophenoxy) butyrate, S-ethyl-
4-chloro-2-methylhexythioacetate, 3-
Isopropyl-2,1,3-benzothiadiazinone-
(4) -2,2-dioxide sodium salt, 2-methylthio-4,6-bis (ethylamino) -s-triazine, 2-methylthio-4-ethylamino-6- (1,2
-Dimethylpropylamino) -s-triazine and 2-
The compound is at least one compound selected from the group consisting of amino-3-chloro-1,4-naphthoquinone.
3. The herbicidal composition according to any one of 3. 6. The herbicidal composition according to claim 1, wherein n in the general formula (I) is 2. 7. The herbicidal composition according to claim 1, wherein R ^{1 to} R ⁶ in the general formula (I) are all hydrogen atoms. 8. X in the general formula (I) is a chlorine atom, a bromine atom, a nitro group, a cyano group, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, or 1 carbon atom.
The herbicidal composition according to any one of claims 1 to 7, which is an alkoxyalkyl group of (1) to (6). 9. The method according to claim 1, wherein Z in the general formula (I) is a hydrogen atom, —S—R ⁷ or —SO ₂ —R ⁷ [R ⁷ is as defined above]. Herbicide composition. 10. The herbicidal composition according to claim 1, wherein m in the general formula (I) is 1.