JPH06256312A - Phenylimidazole derivative, its production, herbicide and its use - Google Patents

Abstract

PURPOSE:To obtain a new phenylimidazole derivative showing excellent herbicidal action on weeds before and after germination with a small amount of agent. CONSTITUTION:A compound of formula I {R<1> is H, alkyl, haloalkyl, alkenyl or alkenyl; R<2> is H, alkyl or haloalkyl; X is H or halogen; Y is halogen; R<3> and BR4 [B is O, S or NH; R<4> is R<1>, cycloalkyl, CH(R<5>)COOR<6> (R<5> is H or alkyl; R<6> is R<4>, alkoxyalkyl or alkoxyalkoxyalkyl), etc.], CO-A-R<9> [A is O or S; R<9> is R<1>, cycloalkyl, CH(R<5>)CO-A-R<10> (R<10> is R<6>), etc.]} such as (5)-(4- chloro-2-fluoro-5-methoxyphenyl)-2-methylimidazole. The compound of formula I wherein R<1> is H and R<2> is H or alkyl is obtained by reacting a compound of formula II (Hal is halogen) with a compound of formula III (R<2-1> is H or alkyl).

Description

Detailed Description of the Invention

[0001]

The present invention relates to the general formula (I)

[Chemical 101] [In the formula, R ¹ is a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, or 3 carbon atoms.
To a lower alkenyl group having 5 to 5 carbon atoms or a lower alkynyl group having 3 to 5 carbon atoms, R ² represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a haloalkyl group having 1 to 5 carbon atoms, and X represents Represents a hydrogen atom or a halogen atom, Y may be the same or different, represents a halogen atom, and R ³ represents

Embedded image -BR ⁴ (wherein B represents O, S or NH, R ⁴ represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, or the number of carbon atoms) An alkenyl group having 3 to 5 carbon atoms, a lower alkynyl group having 3 to 5 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms,

[0002]

Embedded image wherein —CH (R ⁵ ) COOR ⁶ (wherein R ⁵ represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, R ⁶ represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, A haloalkyl group having 1 to 5 carbon atoms, an alkenyl group having 3 to 5 carbon atoms, a lower alkynyl group having 3 to 5 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and a total number of carbon atoms of 2 6 represents an alkoxyalkyl group or a total number of carbon atoms is an alkoxyalkoxyalkyl group having 3 to 9) or

Embedded image --CH (R ⁵ ) CON (R ⁷ ) R ⁸ (In the formula, R ⁵ is the same as defined above, R ⁷ and R ⁸ may be the same or different, and a hydrogen atom or a carbon atom number 1 to 6 alkyl group, R ⁷ and R ⁸ together may represent an alkylene group having 4 to 6 carbon atoms.). } Or

[0003]

Embedded image -CO-AR ⁹ {wherein A represents O or S, R ⁹ represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, or the number of carbon atoms. An alkenyl group having 3 to 5 carbon atoms, a lower alkynyl group having 3 to 5 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms,

Embedded image wherein —CH (R ⁵ ) CO—AR ¹⁰ (wherein R ⁵ and A are the same as defined above, R ¹⁰ is a hydrogen atom,
An alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, an alkenyl group having 3 to 5 carbon atoms, a lower alkynyl group having 3 to 5 carbon atoms, and 3 to 6 carbon atoms
Is a cycloalkyl group, an alkoxyalkyl group having a total number of carbon atoms of 2 to 6 or an alkoxyalkoxyalkyl group having a total number of carbon atoms of 3 to 9. ) Or

Embedded image represents —CH (R ⁵ ) CON (R ⁷ ) R ⁸ (in the formula, R ⁵ , R ⁷ and R ⁸ are the same as defined above). } Is shown. ] It is related with the phenyl imidazole derivative represented by these, its manufacturing method, a herbicide, and a herbicidal method.

[0004]

2. Description of the Related Art Japanese Patent Application Laid-Open No. 2-262560 discloses an imidazole compound represented by the following general formula as an intermediate compound in the production of agricultural and horticultural pest control agents, medicinal fungicides or herbicides. It is disclosed.

[Chemical 108] However, the definition of Y in the above general formula is a hydrogen atom, a chlorine atom or a bromine atom, which is different from the present invention.

[0005]

DISCLOSURE OF THE INVENTION As a result of intensive studies by the present inventors to create a new herbicide, the phenylimidazole derivative of the present invention represented by the general formula (I) has not been described in the literature. The present invention has been completed by discovering that it is a novel compound of 1. and has excellent herbicidal activity at a low dose.

[0006]

The phenylimidazole derivative represented by the general formula (I) of the present invention in which R ¹ represents a hydrogen atom has a tautomer shown below. These tautomers are also included.

[Chemical 109] (In the formula, R ² , R ³ , X and Y are the same as above.)

Among the substituents of the phenylimidazole derivative represented by the general formula (I) of the present invention, preferred substituents include, for example, R ¹ is chloromethyl, dichloromethyl, trichloromethyl, chlorofluoromethyl, Fluoromethyl, difluoromethyl, trifluoromethyl, chloroethyl, dichloroethyl, trichloroethyl, fluoroethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl, chlorodifluoroethyl, dichlorodifluoroethyl, chloropropyl, dichloropropyl,
Fluoropropyl, difluoropropyl, trifluoropropyl, tetrafluoropropyl, pentafluoropropyl, chlorobutyl, dichlorobutyl, fluorobutyl, difluorobutyl, etc., which may be the same or different, selected from chlorine atom, bromine atom, fluorine atom or more Is preferably a haloalkyl group substituted with a halogen atom, particularly preferably a difluoromethyl group or a tetrafluoroethyl group.

Examples of R ² include methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl,
alkyl groups such as t-butyl and n-pentyl, chloromethyl,
A haloalkyl group such as dichloromethyl is preferable, and R ³ is an alkoxy group such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, n-pentiooxy, difluoromethoxy. A haloalkoxy group such as trifluoromethoxy, an alkenyloxy group such as propenyloxy and butenyloxy, an alkynyloxy group such as propynyloxy and putinyloxy, a cycloalkyloxy group such as cyclopropyloxy, cyclopentyloxy and cyclohexyloxy, methoxycarbonylmethyloxy, Ethoxycarbonylmethyloxy, n-propoxycarbonylmethyloxy, i-propoxycarbonylmethyloxy, n-butoxycarbonylmethyloxy, methoxycarbonylethyloxy, ethoxycarbonylethyloxy Alkoxycarbonylalkyloxy groups such as Si, n-propoxycarbonylethyloxy, i-propoxycarbonylethyloxy, n-butoxycarbonylethyloxy, chloromethoxycarbonylmethyloxy, chloroethoxycarbonylmethyloxy, chloropropoxycarbonylmethyloxy, chloromethoxy Carbonylethyloxy, chloroethoxycarbonylethyloxy, haloalkoxycarbonylalkyloxy groups such as chloropropoxycarbonylethyloxy, cyclopropyloxycarbonylmethyloxy, cyclopentylcarbonylmethyloxy, cycloalkyloxycarbonylalkyloxy groups such as cyclohexylcarbonylmethyloxy, Methoxymethoxycarbonylmethyloxy, methoxyethoxycarbonylmethyl Oxy, alkoxyalkoxycarbonylalkyloxy groups such as ethoxyethoxycarbonylalkyloxy,

Alkoxyalkoxyalkoxycarbonyl such as methoxymethoxymethoxycarbonylmethyloxy, methoxyethoxyethoxycarbonylmethyloxy, ethoxyethoxyethoxycarbonylmethyloxy, methoxymethoxymethoxycarbonylethyloxy, methoxyethoxyethoxycarbonylethyloxy and ethoxyethoxyethoxycarbonylethyloxy. Alkyloxy group, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, i-propoxycarbonyl, n-butoxycarbonyl, i-butoxycarbonyl, s-
Alkoxycarbonyl groups such as butoxycarbonyl, t-butoxycarbonyl, n-pentyloxycarbonyl, methoxycarbonylmethoxycarbonyl, ethoxycarbonylmethoxycarbonyl, n-propoxycarbonylmethoxycarbonyl, methoxycarbonylethoxycarbonyl, ethoxycarbonylethoxycarbonyl, n-propoxycarbonyl Alkoxycarbonylalkyloxycarbonyl group such as ethoxycarbonyl, methoxymethoxycarbonylmethoxycarbonyl, methoxyethoxycarbonylmethoxycarbonyl, ethoxyethoxycarbonylmethoxycarbonyl, alkoxyalkoxycarbonylalkoxycarbonyl group such as ethoxyethoxycarbonylethoxycarbonyl, methoxymethoxymethoxycarbonylmethoxycarboxyl Preferred are alkoxyalkoxyalkoxycarbonylalkoxycarbonyl groups such as nyl, methoxyethoxyethoxycarbonylmethoxy, ethoxyethoxyethoxycarbonylmethoxycarbonyl, methoxymethoxymethoxycarbonylethoxycarbonyl, methoxyethoxyethoxycarbonylethoxycarbonyl, and ethoxyethoxyethoxycarbonylethoxycarbonyl. Is preferably a halogen atom such as a chlorine atom or a bromine atom, and Y is preferably a chlorine atom or a fluorine atom.

The phenylimidazole derivative represented by the general formula (I) of the present invention can be produced, for example, by the method shown below. Manufacturing method 1 .

[Chemical 110] [In the formula, R ^2-1 , R ³ , Y and Hal are the same as defined above. This reaction is carried out by reacting the compound represented by the general formula (II) with the compound represented by the general formula (III) in the presence or absence of an inert solvent to give the compound represented by the general formula (I-1) The compounds represented can be prepared. This reaction is described in Chem. Ber. , 86,
88 (1935), Tetrahedron Let
t. , 1967, 265, etc., to obtain the desired product.

Manufacturing method 2 .

[Chemical 111] [In the formula, R ^2-2 , R ³ , R ¹¹ and Y are the same as defined above. This reaction is carried out by reacting a compound represented by the general formula (IV) with an aldehyde represented by the general formula (V) in the presence of aqueous ammonia and a copper salt compound such as copper acetate. I-2)
A phenyl imidazole derivative represented by can be produced. This reaction is based on J. Org. Chem. , 198
The target product can be produced according to the method described in 3, 48, 3745 and the like.

Manufacturing method 3 .

[Chemical 112] [In the formula, R ^1-1 , R ² , R ³ , X, Y and Hal are the same as defined above. ] The phenylimidazole derivative represented by the general formula (I-3) and the halide represented by the general formula (VI) or the general formula (VII) in the presence of a base, and in the presence of an inert solvent, or A phenylimidazole derivative represented by the general formula (I-4) can be produced by reacting in the absence of the compound.

The inert solvent which can be used in this reaction may be an inert solvent which does not markedly hinder the progress of this kind of reaction. For example, aromatic hydrocarbons such as benzene, toluene, xylene, methanol, ethanol and the like. -Le, Propano-
Alcohol, alcohol such as glycol, diethyl ether,
Tetrahydrofuran, ethers such as dioxane, acetone, methyl ethyl ketone, ketones such as cyclohexanone, esters such as ethyl acetate, amides such as dimethylformamide and dimethylacetamide, dimethyl sulfoxide, water and the like can be exemplified. These inert solvents can be used alone or as a mixture.
The reaction temperature for this reaction may be selected from room temperature to the boiling point range of the inert solvent used, and is preferably in the range of 40 ° C to 140 ° C.

As the base that can be used in this reaction, an inorganic base or an organic base can be used. For example, as the inorganic base, sodium carbonate, sodium hydride, sodium hydrogen carbonate, potassium hydrogen carbonate, sodium hydroxide, potassium hydroxide can be used. And the like, and as the organic base, alkali metal alcoholates, trimethylamine, triethylamine, pyridine, diethylaniline,
1,8-diazabicyclo- [5,4,0] -7-undecene and the like can be used. When the reaction is carried out in an organic solvent and an aqueous solvent, a phase transfer catalyst such as tetra-n-butyl-ammonium bromide or triethylbenzylammonium chloride can also be used.

The amount of the base used may be appropriately selected from the equimolar to excess molar range with respect to the phenylimidazole derivative represented by the general formula (I-3), and is preferably 2
It is preferably used in an amount of 10 to 10 times by mole. When a phase transfer catalyst is used, it is used in an amount of 0.01 to equimolar with respect to the phenylimidazole derivative represented by the general formula (I-3). You can use it. Since this reaction is an equimolar reaction, each reaction agent may be used in an equimolar amount, but any one of the reaction agents may be used in excess. The reaction time may be selected from the range of several minutes to 48 hours. After the reaction,
The desired product can be isolated by isolating the reaction solution by a conventional method and, if necessary, purifying it.

Manufacturing method 4

[Chemical 113] [In the formula, R ¹ , R ² , R ³ , X ¹ and Y are the same as defined above. ] General formula
A phenylimidazole derivative represented by general formula (I-6) is produced by halogenating a phenylimidazole derivative represented by (I-5) with a halogenating agent in the presence of an inert solvent. be able to.

Any inert solvent can be used in this reaction so long as it does not significantly inhibit the progress of this reaction. For example, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, benzene, toluene, xylene and the like. Aromatic hydrocarbons, esters such as ethyl acetate, nitriles such as acetonitrile and benzonitrile, chain ethers such as methyl cellosolve diethyl ether, cyclic ethers such as dioxane and tetrahydrofuran, sulfolane , Dimethylformamide, dimethyl sulfone, dimethyl sulfoxide, water, phosphorus oxychloride, glacial acetic acid and the like, and these inert solvents may be used alone or in combination.

As the halogenating agent used in this reaction,
For example, chlorine, phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride, sulfuryl chloride, N-chlorosuccinimide (NC
A halogenating agent such as S), bromine or N-bromosuccinimide (NBS) can be used. The amount of the halogenating agent to be used may be appropriately selected and used from the range of 0.5 mol to excess mol with respect to the phenylimidazole derivative represented by the general formula (I-5). The reaction temperature may be appropriately selected from the range of 0 ° C to the boiling point range of the inert solvent used, and is preferably in the range of 10 ° C to 50 ° C. The reaction time is not constant depending on the reaction scale and the reaction temperature, but may be appropriately selected from the range of several minutes to 48 hours. After completion of the reaction, it is represented by the general formula (I) by a conventional method from the reaction system containing the desired product, for example, operation such as solvent extraction and purification by recrystallization method or column chromatography method as necessary. Phenylimidazole derivatives can be prepared.

Manufacturing Method 5

[Chemical 114] [In the formula, R ¹ , R ² , R ^4-1 , X and Y are the same as defined above. This reaction is carried out by deprotecting the phenylimidazole derivative represented by the general formula (I-7) with a mineral acid, a halogen, a Lewis acid or the like in the presence or absence of an inert solvent. I-8)
A phenyl imidazole derivative represented by can be produced. This reaction is based on J. Am. Chem. Soc. , 7
The target product can be produced according to the production method described in 3,5765 (1951) and the like.

Manufacturing method 6

[Chemical 115] [In the formula, R ¹ , R ² , R ^4-2 , X, Y and Hal are the same as defined above. This reaction is carried out by reacting a phenylimidazole derivative represented by the general formula (I-9) with a halide represented by the general formula (VIII) in the presence or absence of an inert solvent and in the presence of a base. By doing so, the phenylimidazole derivative represented by the general formula (I-10) can be produced.

The inert solvent which can be used in this reaction may be any one which does not markedly hinder the progress of this reaction, for example, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, benzene, toluene, xylene and the like. Aromatic hydrocarbons, esters such as ethyl acetate, nitriles such as acetonitrile and benzonitrile, chain ethers such as methyl cellosolve diethyl ether, cyclic ethers such as dioxane and tetrahydrofuran, sulfolane , Dimethylformamide, dimethyl sulfone, dimethyl sulfoxide, water, etc., and these inert solvents may be used alone or in combination. When using a mixed solvent of water and an organic solvent, a phase transfer catalyst such as triethylbenzylammonium chloride can be used together with a base.

As the base that can be used in this reaction, an inorganic base or an organic base can be used. Examples of the inorganic base include hydroxides of alkali metal or alkaline earth metal atoms such as sodium, potassium, magnesium and calcium. , Carbonate or alcoholate can be used. Examples of the organic base include triethylamine,
Organic bases such as pyridine can be used. Since this reaction is an equimolar reaction, the phenylimidazole derivative represented by the general formula (I-9) and the halides represented by the general formula (VIII) may be used in an equimolar amount. It can also be used in excess. The reaction temperature may be appropriately selected from the range of 0 ° C to the boiling point range of the inert solvent used, and preferably 10 ° C to the boiling point range of the inert solvent used. The reaction time is not constant depending on the reaction scale and the reaction temperature, but may be appropriately selected from the range of several minutes to 48 hours.
After completion of the reaction, the desired product can be produced from the reaction system containing the desired product by an ordinary method, for example, solvent extraction or the like, and if necessary, purification by a recrystallization method or a column chromatography method. .

Manufacturing Method 7

[Chemical formula 116] (In the formula, R ¹ , R ² , X and Y are the same as above.) General formula (XII)
The compound represented by general formula (I It is possible to produce a phenylimidazole derivative represented by -11).

7-1. Nitration reaction Examples of the nitrating agent that can be used in this reaction include concentrated nitric acid or a mixture of fuming nitric acid and concentrated sulfuric acid, and acetyl nitrate produced by mixing concentrated nitric acid and acetic anhydride. As the inert solvent that can be used in this reaction, for example, mineral acids such as sulfuric acid and hydrochloric acid can be used. Since this reaction is an equimolar reaction, the nitrating agent may be used in an equimolar amount to the compound represented by the general formula (XII), but may be used in excess. Reaction temperature is -10 ℃ to 140 ℃
Select from the range of. The reaction time is not constant depending on the reaction amount, reaction temperature, etc., but may be in the range of several minutes to 48 hours. After completion of the reaction, the reaction product containing the desired product may be poured into ice water, and the precipitated crystals may be collected by filtration, or the desired product may be isolated by solvent extraction or the like and purified as necessary to produce the desired product. it can.

7-2. Reduction reaction As an inert solvent which can be used in this reaction, any inert solvent which does not markedly hinder the progress of this reaction may be used.
Examples thereof include alcohols such as alcohol, ethanol and propanol, ethers such as diethyl ether, methyl cellosolve, dioxane and tetrahydrofuran, organic acids such as acetic acid, mineral acids such as hydrochloric acid and water. be able to. As the reducing agent used in this reaction, under acidic conditions, for example, zinc, iron,
Examples thereof include tin and tin chloride, and zinc powder can be used even under basic conditions. Further, in the catalytic hydrogenation method, the reaction can be carried out under normal pressure or under pressure. it can. When the reaction is carried out under acidic conditions, for example, the reducing agent may be used in an equimolar to excess amount, and is generally used in an excess amount.

In the catalytic hydrogenation method, for example, when Raney-nickel or the like is used, 2 to 20% by weight, based on the weight of the compound represented by the general formula (XIII), a noble metal catalyst such as platinum or palladium is used. In this case, the same amount of 0.02 to 5% by weight may be used. The reaction temperature is 0 ° C to 150
It may be selected from the range of ° C. The reaction time is the reaction amount,
Although it does not vary depending on the reaction temperature and the like, it may be performed within a range of several minutes to 48 hours. After completion of the reaction, when the reaction is carried out under acidic conditions, the reaction mixture containing the target substance is poured into ice water, and the target substance is isolated by solvent extraction or the like to make it basic, or in the case of the catalytic hydrogenation method, the reaction liquid is used. The catalyst can be removed by filtration from the above, and the filtrate can be concentrated to isolate the product. If desired, the desired product can be produced by purification by column chromatography or the like.

Manufacturing Method 8

[Chemical 117] (In the formula, R ¹ R ² X and Y are the same as above.) General formula (XII)
The compound represented by general formula (XIV) is subjected to chlorosulfonylation in the presence of an inert solvent to give a compound represented by the general formula (XIV), and then the compound (XIV) is reduced in the presence of an inert solvent to give a compound represented by the general formula (XIV): A phenylimidazole derivative represented by I-12) can be produced.

8-1. Examples of the inert solvent which can be used in this reaction include halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, nitriles such as acetonitrile, ethers such as methyl cellosolve, dioxane and tetrahydrofuran, concentrated sulfuric acid and the like. The mineral acids can be exemplified. For the chlorosulfonylation reaction, chlorosulfonic acid or the like may be used. Sulfonating with fuming sulfuric acid, the sulfonic acid thus formed is converted to an alkali metal salt, and the alkali metal salt is chlorinated with phosphorus pentachloride to obtain the desired chlorosulfonate. Or a method of reacting fuming sulfuric acid and then reacting with carbon tetrachloride to produce the desired chlorosulfonate.

The amount of chlorosulfonic acid used may be selected from an equimolar to excess molar range, preferably an excess amount. The amount of fuming sulfuric acid or carbon tetrachloride used may be appropriately selected from the equimolar to excess molar range.
The reaction temperature may be selected from the range of 0 ° C to 180 ° C. The reaction time is not constant depending on the reaction amount, reaction temperature, etc., but may be in the range of several minutes to 48 hours. After the completion of the reaction, the reaction solution containing the desired product can be poured into water, and the desired product can be isolated by solvent extraction or the like, and the desired product can be produced by purification by column chromatography or the like, if necessary. .

8-2. This reaction may be carried out in the presence of an inert solvent such as glacial acetic acid, and as the reducing agent, for example, zinc, tin, tin chloride or the like can be used, and the amount thereof used is equimolar to excess molar. You can select from the range. The reaction temperature may be selected from the range of 0 ° C to 180 ° C. The reaction time is not constant depending on the reaction amount, reaction temperature, etc., but may be in the range of several minutes to 48 hours. After the completion of the reaction, the reaction solution containing the desired product can be poured into water, and the desired product can be isolated by solvent extraction or the like, and the desired product can be produced by purification by column chromatography or the like, if necessary. .

Manufacturing Method 9

[Chemical 118] [Wherein R ¹ , R ² , X and Y are the same as defined above. This reaction is a phenylimidazole derivative represented by the general formula (I-13) by oxidizing an imidazole represented by the general formula (IX) with an oxidizing agent in the presence of an inert solvent. Can be manufactured.

As the inert solvent which can be used in this reaction,
For example, pyridine, water, etc. can be used in addition to aromatic hydrocarbons such as benzene, toluene, xylene, etc. These inert solvents can be used alone or in a mixture. As the oxidant used in this reaction, for example, potassium permanganate, potassium dichromate, or the like peroxide can be used, and the amount of the oxidant to be used is the imidazole represented by the general formula (IX). On the other hand, it may be appropriately selected from the equimolar to 5 times molar range, preferably 4 to 5 times molar range.

The reaction temperature may be appropriately selected from 0 ° C. to the boiling point range of the inert solvent used, preferably 30 ° C. to 1
It is in the range of 80 ° C. The reaction time is not constant depending on the reaction scale and the reaction temperature, but may be appropriately selected from the range of several minutes to 48 hours. After completion of the reaction, the desired product can be produced from the reaction system containing the desired product by a conventional method, for example, solvent extraction and the like, and if necessary, purification by a recrystallization method or a column chromatography method.

Manufacturing Method 10

[Chemical formula 119] [In the formula, R ¹ , R ² , R ^9-1 , A, X, Y and Hal are the same as defined above. ] The phenylimidazole derivative represented by the general formula (I-13) and the compound represented by the general formula (X) or the general formula (XI) in the presence or absence of an inert solvent, and a base or a catalyst. By reacting in the presence or absence of the general formula (1-14)
A phenyl imidazole derivative represented by can be produced.

When a catalyst is used in this reaction, examples of the catalyst used include mineral acids such as sulfuric acid and hydrochloric acid, organic acids such as paratoluenesulfonic acid, Lewis acids such as boron fluoride etherate, and the like. Dicyclohexylcarbodiimide (DC
C) and the like can be used. This reaction can be carried out in the same manner as in Production method 6 to produce the desired product.
After completion of the reaction, the desired product can be produced from the reaction system containing the desired product by a conventional method, for example, solvent extraction and the like, and if necessary, purification by a recrystallization method or a column chromatography method.

Manufacturing Method 11

[Chemical 120] [Wherein R ¹ , R ³ , X ¹ , Y, Z, p and q are the same as defined above. This reaction is carried out by halogenating the phenylimidazole derivative represented by the general formula (I-15) in the presence or absence of an inert solvent (provided that a fluorine atom is excluded) to give the general formula (I-16 ) The phenyl imidazole derivative represented by these can be manufactured. This reaction can be carried out in the same manner as in Production method 4 to produce the desired product.

Typical compounds of the phenylimidazole derivative represented by the general formula (I) of the present invention are shown in Table 1 below, but the present invention is not limited thereto.

[0038]

[Table 1]

[0039]

[Table 2]

[0040]

[Table 3]

[0041]

[Table 4]

General formula (II), general formula (III), general formulas (IX) and (XII) which are starting compounds for producing the phenylimidazole derivative represented by the general formula (I) of the present invention The compound represented by can be produced, for example, by the following production method. General formula (II) and general formula (III)

[Chemical 121] [In the formula, R ¹ , R ² , R ¹¹ , and Hal are the same as defined above. A compound represented by the general formula (II) is produced by subjecting the compound represented by the general formula (XV) to a Friedel-Crafts reaction, and the compound represented by the general formula (XVI) is isolated or not isolated. The compound represented by the general formula (III) can be produced by reacting with the compound represented.

General formula (IX)

[Chemical formula 122] [Wherein R ¹ , R ² , X, Y and Hal are the same as defined above. A compound represented by the general formula (XV) can be produced by the production method of the present invention, and the compound (XV) can be produced by the production method disclosed in, for example, JP-A-3-163063. it can. The compound represented by the general formula (XII) can be produced according to the production method of the present invention.

Typical examples of the present invention will be given below, but the present invention is not limited thereto.

【Example】

Example 1 4 (5)-(4-chloro-2-fluoro-
Preparation of 5-isopropoxyphenyl) imidazole (Compound No2)

[Chemical 123] 1-Bromo-2- (4-chloro-2-fluoro-5-isopropoxyphenyl) -2-ethanone 1.25 g
(4.04 mmol) was added to 10 ml of formamide, and the reaction was carried out at 160 ° C for 2 hours. After completion of the reaction, the reaction solution was poured into ice water, the desired product was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the obtained crude crystals were recrystallized to obtain the desired product. 0.72 g was obtained. Physical properties mp 152.0-153.0 ° C Yield 7
0.0%

Example 2 4 (5)-(4-chloro-2
Production of -fluoro-5-methoxyphenyl) -2-methylimidazole (Compound No1)

[Chemical formula 124] To 100 ml of 28% ammonia water, 9.55 g (195 mmol) of 90% aqueous acetaldehyde solution and 25.96 g (130 mmol) of copper acetate monohydrate were added under ice cooling.
Thereafter, 16.94 g of 1-acetoxy-2- (4-chloro-2-fluoro-5-methoxyphenyl) -2-ethanone dissolved in 100 ml of dimethylformamide at room temperature.
(65 mmol) was added dropwise, and after the addition was completed, the reaction was carried out at room temperature for 3 hours, and further at 100 ° C. for 20 minutes. After completion of the reaction, the reaction solution containing the desired product was poured into ice water, and the precipitated precipitate was collected by filtration. The precipitate was gradually added to 185 ml of concentrated sulfuric acid and stirred at room temperature for 6 hours. The target product was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to recrystallize the obtained crude crystal to obtain 7.71 g of the desired product. Physical properties mp205.0-
207.0 ° C Yield 49.3%

Example 3 Preparation of 4- (4-chloro-2-fluoro-5-methoxyphenyl) -1-difluoromethyl-2-methylimidazole (Compound No. 12)

[Chemical 125] 2.41 g (10) of 4 (5)-(4-chloro-2-fluoro-5-methoxyphenyl) -2-methylimidazole
Mmol) and 1.38 g (20 mmol) of potassium carbonate were added to 50 ml of dimethylformamide, and the reaction was carried out at 90 ° C. for 4 hours while blowing chlorodifluoromethane (Freon-22 gas). After completion of the reaction, the reaction solution containing the desired product was poured into ice water, extracted with ethyl acetate, the extract was washed with water and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure to obtain 2.90 g of an oily substance. Obtained.
The obtained oily substance was purified by dry column chromatography to obtain 1.86 g of the desired product. Physical property mp
74.0-75.6 ° C Yield 64.0%

Example 4 Preparation of 5-chloro-4- (4-chloro-2-fluoro-5-methoxyphenyl) -1-difluoromethyl-2-methylimidazole (compound
No22)

[Chemical formula 126] 1.27 g (4.37 mmol) of 4- (4-chloro-2-fluoro-5-methoxyphenyl) -1-difluoromethyl-2-methylimidazole was added to 50 ml of carbon tetrachloride.
Was dissolved in, and sulfuryl chloride (0.65 g, 4.81 mmol) was added under ice-cooling, the reaction was carried out for 3 hours, and the reaction was further carried out at room temperature for 2 hours. After completion of the reaction, an aqueous sodium hydrogen carbonate solution and dichloromethane were added to the reaction solution containing the desired product to extract the desired product, and the extract was washed with water and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The crude crystals were purified by dry column chromatography to obtain 0.65 g of the desired product. Physical properties mp122.0
-123.0 ° C Yield 45.7%

Example 5 Preparation of 5-chloro-4- (4-chloro-2-fluoro-5-hydroxyphenyl) -1-difluoromethyl-2-methylimidazole (Compound No 21)

[Chemical 127] 5-chloro-4- (4-chloro-2-fluoro-5-isopropoxyphenyl) -1-difluoromethyl-2-
2.10 g (5.95 mmol) of methyl imidazole was dissolved in 10 ml of concentrated sulfuric acid and reacted at room temperature for 1 hour. After the reaction is complete, pour the reaction solution containing the desired product into ice water,
After extraction with ether, the extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 1.83 g of the desired product. Physical properties mp159.0-16
3.0 ° C Yield 98.9%

Example 6 5-chloro-4- (4-chloro-2-fluoro-5- (2-propynyloxy) phenyl) -1-difluoromethyl-2-methylimidazo-
Production of compound (Compound No25)

[Chemical 128] 0.48 g (1.56 mmol) of 5-chloro-4- (4-chloro-2-fluoro-5-hydroxyphenyl) -1-difluoromethyl-2-methylimidazole, 0.11 g of potassium carbonate (0. 86 mmol) and 0.20 g (1.72 mmol) propargyl bromide in acetone 2
In addition to 0 ml, the reaction was carried out under reflux for 4 hours. After the reaction was completed, the reaction mixture containing the target substance was poured into ice water, the target substance was extracted with ethyl acetate, the extract was washed with water and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The crude crystal was purified by recrystallization to obtain 0.43 g of the desired product. Physical properties mp104.0-104.6 ° C Yield 7
8.9%

Example 7 Preparation of 5-chloro-4- (4-chloro-2-fluoro-5-methoxycarbonylmethoxyphenyl) -1-difluoromethyl-2-methylimidazole (Compound No 27)

[Chemical formula 129] 0.50 g (1.61 mmol) of 5-chloro-4- (4-chloro-2-fluoro-5-hydroxyphenyl) -1-difluoromethyl-2-methylimidazole, 0.13 g of potassium carbonate (0. 97 mmol) and 0.30 g (1.96 mmol) methyl bromoacetate in acetone 3
In addition to 0 ml, the reaction was carried out under reflux for 4 hours. After completion of the reaction, the reaction solution containing the desired product was poured into ice water, the desired product was extracted with ethyl acetate, the extract was washed with water and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. Page
The striation-like substance was purified by dry column chromatography to obtain 0.52 g of the desired product. Physical properties mp8
8.5-90.0 ° C Yield 84.3%

Example 8 5- (5-chloro-1-difluoromethyl-2-methylimidazol-4-yl)-
Production of 2,4-dichlorobenzoic acid (Compound No 14)

[Chemical 130] 0.85 g (2.5 mmol) of 5- (5-chloro-1-difluoromethyl-2-methylimidazol-4-yl) -2,4-dichlorobenzaldehyde was added to 10 ml of water and heated to 80 ° C. After warming, 0.55 g (3.5 mmol) of potassium permanganate dissolved in 11 ml of water was added dropwise to the reaction solution, and the reaction was carried out for 1.5 hours. After the reaction,
The reaction solution was made alkaline with an aqueous sodium hydroxide solution, the by-produced manganese dioxide was filtered off, the filtrate was acidified with hydrochloric acid, the target product was extracted with ether, and the extract was washed with water and dried over anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure to obtain 0.54 g of the desired product. Physical properties mp2
04.0-207.0 ° C Yield 60.7%

Example 9 5- (5-chloro-1-difluoromethyl-2-methylimidazol-4-yl)-
Production of methyl 2,4-dichlorobenzoate (Compound No1
5)

[Chemical 131] 0.40 g (1.12 mmol) of 5- (5-chloro-1-difluoromethyl-2-methylimidazol-4-yl) -2,4-dichlorobenzoic acid was added to 30 ml of methanol.
Was dissolved in and a catalytic amount of concentrated hydrochloric acid was added, and the mixture was reacted under reflux for 14 hours. After completion of the reaction, the reaction solution containing the desired product was poured into ice water, the desired product was extracted with ethyl acetate, the extract was washed with water and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The paste-like substance was purified by dry column chromatography to obtain 0.24 g of the desired product. Physical properties mp100.2-102.0 ° C Yield
57.7%

Example 10 5- (5-chloro-1-difluoromethyl-2-methylimidazol-4-yl)
Preparation of 2-propynyl-2,4-dichlorobenzoate (Compound No 16)

[Chemical 132] 5- (5-chloro-1-difluoromethyl-2-methylimidazol-4-yl) -2,4-dichlorobenzoic acid 0.40 g (1.12 mmol), potassium carbonate 0.0
9 g (0.67 mmol) and propargyl bromide 0.1
6 g (1.34 mmol) of dimethylformamide 10
In addition to ml, the reaction was carried out at 40 to 50 ° C for 3 hours. After completion of the reaction, the reaction solution containing the desired product was poured into ice water, the desired product was extracted with ethyl acetate, the extract was washed with water and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The crude product was purified by recrystallization to obtain 0.33 g of the desired product.
Got Physical properties mp123.5-124.2 ° C Yield 74.5%

Example 11 5-chloro-4- (4-chloro-2-fluoro-5-isopropoxyphenyl)-
Production of 2-chloromethyl-1-difluoromethyl imidazole (Compound No 46)

[Chemical 133] 5-chloro-4- (4-chloro-2-fluoro-5-isopropoxyphenyl) -1-difluoromethyl-2-
1.77 g (5 mmol) of methyl imidazole was dissolved in 50 ml of carbon tetrachloride, and sulfuryl chloride 1.3 was added to the solution.
5 g (10 mmol) was added dropwise and the reaction was carried out under reflux for 4 hours. After completion of the reaction, dichloromethane and saturated aqueous sodium hydrogen carbonate solution were added to the reaction solution, the organic layer was separated, washed with water and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure to obtain a paste form. By purifying the substance by dry column chromatography, the target compound 1.07
g was obtained. Physical properties nD1.5540 (19 ℃) Yield
55.2%

The herbicide containing the phenylimidazole derivative represented by the general formula (I) of the present invention as an active ingredient is
For example, Novier (common name for "Tainubier", 1st grass of grass family, severely damaging grass of paddy field), Tamiya Cyperus (1st year grass of Cyperaceae family, harmful grass of paddy field), Matsubai (Perennial cyperaceae family, swamp, waterway, paddy field, paddy field , Perennial herbaceous plants), Urikawa (Oldaceae, perennial herbaceous plants that occur in paddy fields, wetlands, and ditches), Firefly (Cyperaceae perennial,
Occurring in paddy fields, wetlands, ditches, oats (perennial grasses,

Plains, wastelands, and fields), mugwort (Asteraceae perennial grass, occurring in the mountains and fields), honeygrass (1st year grass, representative crops of fields and orchards), Rumex japonicus (Polygonaceae) Perennial grasses, fields, and roadsides), Kogomeka Cyper (1st year cyperaceae family, Aobiyu (1st year grass family, vacant land, roadside, field), Ona fir (Asteraceae 1st year grass,
Harmful grass in the field), velvetleaf (1st year mallow, Harm in the field), Morning glory (1st year bindweed, 1st class grass in the field, Harmweed in the field) Grass), Yaemgra (Rubiaceae 1
Paddy fields, fields, orchards
It is useful for weeding annual and perennial weeds that occur in wetlands.

The herbicide containing the phenylimidazole derivative represented by the general formula (I) of the present invention as an active ingredient exhibits an excellent herbicidal effect on weeds before and after emergence, and is therefore a useful plant. Of the herbicide of the present invention by pretreating the planned site for planting, or after planting the useful plant (including the case where the useful plant has already been planted as in a garden) A characteristic physiological activity can be effectively expressed.

However, the herbicide of the present invention should not be used only in such an embodiment. For example, the herbicide of the present invention can be used not only as a herbicide for paddy fields, but also for the weeding of general weeds. It can also be used as an agent. It can also be used to control general weeds. In this case, it is economically most effective to treat the weeds by the first stage of development, but the treatment is not necessarily limited to this, and it is possible to control the weeds in the growing season.

When the phenylimidazole derivative represented by the general formula (I) of the present invention is used as a herbicide, it is prepared in a convenient shape according to a conventional method for pesticide preparation. It is common. That is, the phenylimidazole derivative represented by the general formula (I) of the present invention, these are dissolved in a suitable inert carrier, or optionally together with an auxiliary agent, in a suitable ratio, It may be separated, suspended, mixed, impregnated, adsorbed or attached, and then used by formulating into an appropriate dosage form such as a suspension, emulsion, liquid, wettable powder, granule, powder or tablet.

The inert carrier which can be used in the present invention may be either solid or liquid, and examples of the material which can be a solid carrier include soybean flour, cereal flour, wood flour, bark flour, sawdust powder, Tobacco stem powder, walnut shell powder, bran, fibrin powder, residue after extraction of plant extracts, synthetic polymers such as ground synthetic resin, clays (eg kaolin, bentonite, acid clay, etc.), talcs (eg talc, pyrophyllide) Etc.), silicas (for example, diatomaceous earth, silica sand, mica, white carbon [hydrogenated finely divided silicon, synthetic highly dispersed silicic acid also referred to as hydrous silicic acid, and some products include calcium silicate as a main component]), activated carbon, Sulfur powder, pumice stone, calcined diatomaceous earth, brick crushed material, fly ash, sand, inorganic mineral powder such as calcium carbonate, calcium phosphate, ammonium sulfate,
Examples thereof include chemical fertilizers such as ammonium phosphate, ammonium nitrate, urea, ammonium chloride, and compost, which are used alone or in the form of a mixture of two or more kinds.

The material which can be used as a liquid carrier is selected from those having solvent ability per se, and those having no solvent ability but capable of dispersing an active ingredient compound with the aid of an auxiliary agent. The following carriers can be given as typical examples, and these carriers are used alone or in the form of a mixture of two or more kinds, and for example, water, alcohols (for example, methanol, ethanol, isopropanol, butanol). -, Ethylene glycol, etc.), ketones (for example, acetone, methyl ethyl ketone, methyl isobutyl ketone,
Diisobutyl ketone, cyclohexanone, etc.), ethers (eg ethyl ether, dioxane, cellosolve,
Dipropyl ether, tetrahydrofuran etc.), aliphatic hydrocarbons (eg kerosene, mineral oil etc.), aromatic hydrocarbons (eg benzene, toluene, xylene, solvent naphtha, alkylnaphthalene etc.), halogenated hydrocarbons (eg dichloroethane) , Chloroform, carbon tetrachloride, chlorinated benzene, etc.), esters (eg ethyl acetate, diisopropyl phthalate, dibutyl phthalate, diocluphthalate etc.), amides (eg dimethylformamide, diethylformamide, dimethylacetamide) Etc.), nitriles (for example, acetonitrile, etc.), dimethyl sulfoxides, and the like.

As the other auxiliary agents, the following representative auxiliary agents can be mentioned. These auxiliary agents are used depending on the purpose, and they may be used alone or, in some cases, in combination of two or more kinds. However, in some cases it is also possible to use no adjuvant at all. A surfactant is used for the purpose of emulsifying, dispersing, solubilizing and / or wetting the active ingredient compound, for example, polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene higher fatty acid. Ester, polyoxyethylene resin acid ester, polyoxyethylene sorbitan monolaurate,

Examples of the surface active agent include polyoxyethylene sorbitan monooleate, alkyl aryl sulfonate, naphthalene sulfonic acid condensate, lignin sulfonate, and higher alcohol sulfate.
In addition, for the purpose of stabilizing the dispersion of active ingredient compounds, adhering and / or binding, auxiliary agents exemplified below can be used, for example, casein, gelatin, starch, methyl cellulose, carboxymethyl cellulose. It is also possible to use auxiliary agents such as gum arabic, polyvinyl alcohol, pine oil, bran oil, bentonite and lignin sulfonate. The following auxiliaries can also be used for improving the flowability of the solid product, for example waxes, stearates, alkyl phosphates and the like. As a deflocculant for a suspending product, an auxiliary agent such as a naphthalenesulfonic acid condensate or a condensed phosphate can be used. As the defoaming agent, for example, an auxiliary agent such as silicone oil may be used.

The compounding ratio of the active ingredient compound can be adjusted according to need. For example, 0.01 to 50% by weight in the case of powder or granules, and 0. 01 to 50% by weight is suitable. The herbicide containing the phenylimidazole derivative represented by the general formula (I) of the present invention as an active ingredient is used as it is for killing various weeds or suppressing the growth, or appropriately diluted with water, or suspended. An amount effective for killing or suppressing growth in a turbid form may be applied to the weed, or applied to foliage or soil in a place where the development or growth of the weed is not preferable.

The amount of the herbicide containing the phenylimidazole derivative represented by the general formula (I) of the present invention as an active ingredient depends on various factors such as the purpose, the target weeds, the growing condition of the crops and the occurrence of the weeds. It varies depending on the tendency, weather, environmental conditions, dosage form, application method, application place, application time, etc., but 0.01 g to 10 kg per hectare as an active ingredient compound
It may be appropriately selected from the range according to the purpose. Weeds containing a phenylimidazole derivative represented by the general formula (I) of the present invention as an active ingredient are further weeds to be controlled, other herbicides for the purpose of expanding the appropriate control period or for the purpose of reducing the dosage. It is also possible to use it by mixing with an agent. Typical formulation examples and test examples of the present invention are shown below, but the present invention is not limited thereto. In the prescription examples, “part” means “part by weight”.

Formulation Example 1 Compound of the present invention 50 parts Xylene 40 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzene sulfonate 10 parts The above are uniformly mixed and dissolved to obtain an emulsion. Formulation Example 2 Compound of the present invention 3 parts Cray powder 82 parts Diatomaceous earth powder 15 parts The above are uniformly mixed and pulverized to give a powder.

Formulation Example 3 Compound of the present invention 5 parts Mixed powder of bentonite and clay 90 parts 5 parts Calcium lignin sulfonate 5 parts
Dry to make granules. Formulation Example 4 Compound of the present invention 20 parts Kaolin and synthetic highly dispersed silicic acid 75 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzene sulfonate 5 parts The above are uniformly mixed and pulverized to obtain a wettable powder.

Test Example 1 Herbicidal effect test against paddy field weeds after emergence: Soil was packed in a 1 / 1000-all pot to make a paddy field,
The seeds of paddy field weeds Novier (EC), firefly (SJ), and soul stalks of Mizugayatsuri (CS) and Urikawa (SP) were adjusted to the one-leaf stage. This was treated with a predetermined amount of a drug solution containing a compound of the present invention (compounds listed in Table 1) as an active ingredient. 21 days after the treatment, the herbicidal effect was investigated, the herbicidal rate was calculated in comparison with the untreated, and the judgment was made according to the following criteria. At the same time, a chemical damage to rice was also investigated and judged according to the following criteria.

Criteria for herbicidal activity: 5 ... 95% or more herbicidal rate. 4 ... 70% or more and less than 95% herbicidal rate. 3 ... 50% or more and less than 70% herbicidal rate. 2 ... 30% or more and less than 50% herbicidal rate. 1 ... 10% or more and less than 30% herbicidal rate. 0 ... less than 10% herbicide rate. Criteria for determination of phytotoxicity: H: large phytotoxicity (including death) M: medium phytotoxicity L: low phytotoxicity N: no phytotoxicity The results are shown in Table 2.

[0071]

[Table 5]

[0072]

[Table 6]

[0073]

[Table 7]

Test Example 2 Herbicidal effect on field weeds before emergence: A polyethylene vat having a length of 10 cm, a width of 20 cm, and a height of 5 cm is filled with soil, and the field weeds are wild oats (AF), millet (EC), and citrus. (AT), Ona fir (XS), Yaemgra (GA), O.
P) and soybean and wheat seeds as field crops were sown and covered. Compounds of the present invention (compounds listed in Table 1)
A drug containing as an active ingredient was treated as a spray liquid having a predetermined concentration. The herbicidal effect was investigated 14 days after the treatment, and the herbicidal rate was calculated and judged in the same manner as in Test Example 1. At the same time, phytotoxicity to soybean and wheat was investigated, and judgment was made according to Test Example 1. The results are shown in Table 3.

[0075]

[Table 8]

[0076]

[Table 9]

[0077]

[Table 10]

Test Example 3 Herbicidal effect on field weeds after emergence: A polyethylene vat having a length of 10 cm × width of 20 cm × height of 5 cm was filled with soil, and seeds of soybeans and wheat trees were sown as the following harmful landweeds and field crops. It was covered with soil and grown to the leaf stage below, and a drug containing the compound of the present invention (compounds shown in Table 1) as an active ingredient was applied thereto as a spray solution having a predetermined concentration. The herbicidal effect was investigated 14 days after the treatment, and the herbicidal rate was calculated and judged in the same manner as in Test Example 1. At the same time, phytotoxicity to soybean and wheat was investigated, and judgment was made according to Test Example 1.

Test weed species and their leaf stages and soybean and wheat leaf stages. Wild oat (AF) 2-leaf stage Flies (EC) 2-leaf stage Betula (AT) 1-leaf stage Onami (XS) 1-leaf stage Yaemgra (GA) 2-leaf stage Oennotofugi (VP) 1-leaf stage Wheat 2-leaf stage Soybean 1 leaf The results are shown in Table 4.

[0080]

[Table 11]

[0081]

[Table 12]

[0082]

[Table 13]

[0083]

[Table 14]

Claims (17)

[Claims] 1. A compound represented by the general formula (I): [In the formula, R ¹ is a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, or 3 carbon atoms.
To a lower alkenyl group having 3 to 5 carbon atoms or a lower alkynyl group having 3 to 5 carbon atoms, R ² represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a haloalkyl group having 1 to 5 carbon atoms, and X represents A hydrogen atom or a halogen atom, Y may be the same or different, a halogen atom, R ³ is: embedded image --BR ⁴ {in the formula, B represents O, S or NH, R ⁴ represents hydrogen; Atom, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 5 carbon atoms, alkenyl group having 3 to 5 carbon atoms, lower alkynyl group having 3 to 5 carbon atoms, and 3 to 6 carbon atoms A cycloalkyl group, -CH (R ⁵ ) COOR ⁶ (wherein, R ⁵ represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, R ⁶ represents a hydrogen atom or 1 to 10 carbon atoms) Alkyl group, haloalkyl group having 1 to 5 carbon atoms, alkenyl group having 3 to 5 carbon atoms, carbon A lower alkynyl group having 3 to 5 atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkoxyalkyl group having 2 to 6 carbon atoms in total, or an alkoxyalkoxyalkyl group having 3 to 9 carbon atoms in total. Or CH-R (R ⁵ ) CON (R ⁷ ) R ⁸ (In the formula, R ⁵ may be the same as defined above, R ⁷ and R ⁸ may be the same or different, and may be a hydrogen atom or a carbon atom. It represents an alkyl group having 1 to 6 atoms, and R ⁷ and R ⁸ together may represent an alkylene group having 4 to 6 carbon atoms). } Or embedded image --CO-AR ⁹ {wherein A represents O or S, R ⁹ represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, or carbon. An alkenyl group having 3 to 5 atoms, a lower alkynyl group having 3 to 5 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and -CH (R ⁵ ) CO-AR ¹⁰ (wherein R is ⁵ and A are the same as above, R ¹⁰ is a hydrogen atom,
An alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, an alkenyl group having 3 to 5 carbon atoms, a lower alkynyl group having 3 to 5 carbon atoms, and 3 to 6 carbon atoms
Is a cycloalkyl group, an alkoxyalkyl group having a total number of carbon atoms of 2 to 6 or an alkoxyalkoxyalkyl group having a total number of carbon atoms of 3 to 9. ) Or embedded image —CH (R ⁵ ) CON (R ⁷ ) R ⁸ (in the formula, R ⁵ , R ⁷ and R ⁸ are the same as defined above). } Is shown. ] The phenyl imidazole derivative represented by these. 2. R ¹ represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms or a haloalkyl group having 1 to 5 carbon atoms, and R ² represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or carbon. Represents a haloalkyl group having 1 to 5 atoms, X represents a hydrogen atom or a halogen atom, Y may be the same or different, and represents a halogen atom, and R ³ is a compound represented by the formula: —BR ⁴ {in the formula, B Represents an oxygen atom, R ⁴ represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 3 to 5 carbon atoms, a lower alkynyl group having 3 to 5 carbon atoms, and 3 to 6 carbon atoms. A cycloalkyl group or a —CH (R ⁵ ) COOR ⁶ (in the formula, R ⁵ represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, and R ⁶ represents an alkyl group having 1 to 10 carbon atoms) , A haloalkyl group having 1 to 5 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, the total number of carbon atoms There shows a.) The alkoxyalkyl group or the total number of carbon atoms of 2-6 indicates alkoxyalkoxyalkyl group of 3-9. } Or embedded image --CO-AR ⁹ {in the formula, A represents O, R ⁹ is a hydrogen atom, and has 1 to 10 carbon atoms.
An alkyl group having 10 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or -CH (R ⁵ ) CO-AR ¹⁰ (wherein R ⁵ and A are as described above). And R ¹⁰ is a hydrogen atom,
Alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 5 carbon atoms, cycloalkyl group having 3 to 6 carbon atoms, alkoxyalkyl group having 2 to 6 total carbon atoms, or total number of carbon atoms Represents an alkoxyalkoxyalkyl group of 3 to 9. ) Is shown. } Is shown. ] The phenyl imidazole derivative of Claim 1 represented by these. 3. R ¹ represents a haloalkyl group having 1 to 5 carbon atoms, R ² represents an alkyl group having 1 to 5 carbon atoms, and X
Represents a halogen atom, Y may be the same or different,
Represents a halogen atom, R ³ is: embedded image --BR ⁴ {wherein B represents an oxygen atom, and R ⁴ has 1 to 10 carbon atoms.
An alkyl group having 3 to 5 carbon atoms, an alkenyl group having 3 to 5 carbon atoms, a lower alkynyl group having 3 to 5 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or -CH (R ⁵ ) COOR ⁶ (formula Among them, R ⁵ represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, R ⁶ is an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and the total number of carbon atoms is 2 to 6 alkoxyalkyl group or an alkoxyalkoxyalkyl group having a total number of carbon atoms of 3 to 9). } Or embedded image --CO-AR ⁹ {wherein A represents O, R ⁹ represents an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or CH (R ⁵ ) CO-AR ¹⁰ (In the formula, R ⁵ and A are the same as defined above, and R ¹⁰ is an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and the number of carbon atoms. Represents an alkoxyalkyl group having a sum of 2 to 6 or an alkoxyalkoxyalkyl group having a sum of carbon atoms of 3 to 9). } Is shown. ] The phenyl imidazole derivative of Claim 2 represented by these. 4. A compound represented by the general formula (II): [In the formula, Y may be the same or different and represents a halogen atom, R ³ is: embedded image --BR ⁴ {wherein B represents O, S or NH, R ⁴ represents a hydrogen atom or a carbon atom. An alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, an alkenyl group having 3 to 5 carbon atoms, a lower alkynyl group having 3 to 5 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, Embedded image wherein —CH (R ⁵ ) COOR ⁶ (wherein R ⁵ represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, R ⁶ represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, A haloalkyl group having 1 to 5 carbon atoms, an alkenyl group having 3 to 5 carbon atoms, a lower alkynyl group having 3 to 5 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and a total number of carbon atoms of 2 6 alkoxyalkyl group or an alkoxyalkoxyalkyl group having 3 to 9 carbon atoms in total is shown. Or --CH (R ⁵ ) CON (R ⁷ ) R ⁸ (wherein R ⁵ is the same as defined above, R ⁷ and R ⁸ may be the same or different, and a hydrogen atom or a carbon atom). It represents an alkyl group having 1 to 6 atoms, and R ⁷ and R ⁸ together may represent an alkylene group having 4 to 6 carbon atoms). } Or embedded image --CO-AR ⁹ {wherein A represents O or S, R ⁹ represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, or carbon. An alkenyl group having 3 to 5 atoms, a lower alkynyl group having 3 to 5 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and -CH (R ⁵ ) CO-AR ¹⁰ (in the formula, R ⁵ and A are the same as above, R ¹⁰ is a hydrogen atom,
An alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, an alkenyl group having 3 to 5 carbon atoms, a lower alkynyl group having 3 to 5 carbon atoms, and 3 to 6 carbon atoms
Is a cycloalkyl group, an alkoxyalkyl group having a total number of carbon atoms of 2 to 6 or an alkoxyalkoxyalkyl group having a total number of carbon atoms of 3 to 9. ) Or embedded image —CH (R ⁵ ) CON (R ⁷ ) R ⁸ (in the formula, R ⁵ , R ⁷ and R ⁸ are the same as defined above). } Is shown and Hal shows a halogen atom. ] And a compound represented by the general formula (III): [In the formula, R ^2-1 represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms. ] The compound of the general formula (I-1) characterized by reacting with a compound represented by [In the formula, R ^2-1 , R ³ and Y are the same as defined above. ] The manufacturing method of the phenyl imidazole derivative represented by these. 5. A compound represented by the general formula (IV): [In the formula, Y may be the same or different and each represents a halogen atom, R ³ represents a compound represented by the formula: -BR ⁴ {wherein B represents O, S or NH, R ⁴ represents a hydrogen atom or a carbon atom. An alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, an alkenyl group having 3 to 5 carbon atoms, a lower alkynyl group having 3 to 5 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, Embedded image wherein —CH (R ⁵ ) COOR ⁶ (in the formula, R ⁵ represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, R ⁶ represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, A haloalkyl group having 1 to 5 carbon atoms, an alkenyl group having 3 to 5 carbon atoms, a lower alkynyl group having 3 to 5 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and a total number of carbon atoms of 2 6 alkoxyalkyl group or an alkoxyalkoxyalkyl group having 3 to 9 carbon atoms in total is shown. Or --CH (R ⁵ ) CON (R ⁷ ) R ⁸ (wherein R ⁵ is the same as defined above, R ⁷ and R ⁸ may be the same or different, and is a hydrogen atom or a carbon atom). Represents an alkyl group having 1 to 6 atoms, and R ⁷ and R ⁸ together may represent an alkylene group having 4 to 6 carbon atoms). } Or embedded image --CO-AR ⁹ {wherein A represents O or S, and R ⁹ represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, or carbon. An alkenyl group having 3 to 5 atoms, a lower alkynyl group having 3 to 5 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and -CH (R ⁵ ) CO-AR ¹⁰ (wherein R is ⁵ and A are the same as above, R ¹⁰ is a hydrogen atom,
An alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, an alkenyl group having 3 to 5 carbon atoms, a lower alkynyl group having 3 to 5 carbon atoms, and 3 to 6 carbon atoms
Is a cycloalkyl group, an alkoxyalkyl group having a total number of carbon atoms of 2 to 6 or an alkoxyalkoxyalkyl group having a total number of carbon atoms of 3 to 9. ) Or embedded image embedded image is —CH (R ⁵ ) CON (R ⁷ ) R ⁸ (in the formula, R ⁵ , R ⁷ and R ⁸ are the same as defined above). } Is shown and R ¹¹ represents an alkyl group having 1 to 5 carbon atoms. And a compound represented by the general formula (V): embedded image R ^2-2 —CHO (V) [wherein R ^2-2 represents an alkyl group having 1 to 5 carbon atoms]. ] The aldehydes represented by the general formula (I
-2) [Chemical 33] [In the formula, R ^2-2 , R ³ and Y are the same as defined above. ] The manufacturing method of the phenyl imidazole derivative represented by these. 6. A compound represented by the general formula (I-3): [In the formula, R ² represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a haloalkyl group having 1 to 5 carbon atoms, X represents a hydrogen atom or a halogen atom, and Y may be the same or different. , a halogen atom, R ³ is embedded image -BR ⁴ {wherein, B is O, S or NH, R ⁴ is a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, C 1 -C To haloalkyl group having 3 to 5 carbon atoms, alkenyl group having 3 to 5 carbon atoms, lower alkynyl group having 3 to 5 carbon atoms, cycloalkyl group having 3 to 6 carbon atoms, and -CH (R ⁵ ) COOR ⁶ (In the formula, R ⁵ represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, R ⁶ represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a carbon atom. Alkenyl group having 3 to 5 carbon atoms, lower alkynyl group having 3 to 5 carbon atoms, cyclo having 3 to 6 carbon atoms An alkyl group, an alkoxyalkyl group having a total number of carbon atoms of 2 to 6 or an alkoxyalkoxyalkyl group having a total number of carbon atoms of 3 to 9) or embedded image —CH (R ⁵ ) CON (R ⁷ ) R ⁸ (in the formula, R ⁵ is the same as above, R ⁷ and R ⁸ may be the same or different, and represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and R ⁷ and R ⁸ are the same. Can also represent an alkylene group having 4 to 6 carbon atoms). } Or embedded image --CO-AR ⁹ {wherein A represents O or S, R ⁹ represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, or carbon. An alkenyl group having 3 to 5 atoms, a lower alkynyl group having 3 to 5 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and -CH (R ⁵ ) CO-AR ¹⁰ (wherein R is ⁵ and A are the same as above, R ¹⁰ is a hydrogen atom,
An alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, an alkenyl group having 3 to 5 carbon atoms, a lower alkynyl group having 3 to 5 carbon atoms, and 3 to 6 carbon atoms
Is a cycloalkyl group, an alkoxyalkyl group having a total number of carbon atoms of 2 to 6 or an alkoxyalkoxyalkyl group having a total number of carbon atoms of 3 to 9. ) Or embedded image —CH (R ⁵ ) CON (R ⁷ ) R ⁸ (in the formula, R ⁵ , R ⁷ and R ⁸ are the same as defined above). } Is shown. ] The phenyl imidazole derivative represented by
(VI) embedded image R ^1-1 —Hal (VI) [wherein, R ^1-1 is an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, or 3 to 3 carbon atoms] 5 is a lower alkenyl group or a lower alkynyl group having 3 to 5 carbon atoms, and Hal is a halogen atom. ] Or a halide of the general formula (VII) [In the formula, Hal may be the same or different and represents a halogen atom. ] The general formula (I-4) characterized by reacting with a halide represented by [In the formula, R ^1-1 , R ² , R ³ , X and Y are the same as defined above. ] The manufacturing method of the phenyl imidazole derivative represented by these. 7. A compound represented by the general formula (I-5): [In the formula, R ¹ is a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, or 3 carbon atoms.
To a lower alkenyl group having 3 to 5 carbon atoms or a lower alkynyl group having 3 to 5 carbon atoms, R ² represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a haloalkyl group having 1 to 5 carbon atoms, and Y represents They may be the same or different and each represents a halogen atom, R ³ is: embedded image --BR ⁴ {wherein B represents O, S or NH, R ⁴ is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms. Group, haloalkyl group having 1 to 5 carbon atoms, alkenyl group having 3 to 5 carbon atoms, lower alkynyl group having 3 to 5 carbon atoms, cycloalkyl group having 3 to 6 carbon atoms, (R ⁵ ) COOR ⁶ (In the formula, R ⁵ represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, R ⁶ represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or 1 to 5 carbon atoms. A haloalkyl group, an alkenyl group having 3 to 5 carbon atoms, a lower alkynyl group having 3 to 5 carbon atoms, A cycloalkyl group having 3 to 6 carbon atoms, an alkoxyalkyl group having 2 to 6 carbon atoms in total, or an alkoxyalkoxyalkyl group having 3 to 9 carbon atoms in total) or (R ⁵ ) CON (R ⁷ ) R ⁸ (In the formula, R ⁵ is the same as defined above, R ⁷ and R ⁸ may be the same or different, and represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. , R ⁷ and R ⁸ together may represent an alkylene group having 4 to 6 carbon atoms). } Or embedded image --CO-AR ⁹ {wherein A represents an oxygen atom or a sulfur atom, R ⁹ represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or 1 to 1 carbon atoms.
A haloalkyl group having 5 carbon atoms, an alkenyl group having 3 to 5 carbon atoms, a lower alkynyl group having 3 to 5 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and -CH (R ⁵ ) CO-AR ¹⁰ (In the formula, R ⁵ and A are as defined above, R ¹⁰ is a hydrogen atom,
An alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, an alkenyl group having 3 to 5 carbon atoms, a lower alkynyl group having 3 to 5 carbon atoms, and 3 to 6 carbon atoms
Is a cycloalkyl group, an alkoxyalkyl group having a total number of carbon atoms of 2 to 6 or an alkoxyalkoxyalkyl group having a total number of carbon atoms of 3 to 9. ) Or embedded image represents —CH (R ⁵ ) CON (R ⁷ ) R ⁸ (in the formula, R ⁵ , R ⁷ and R ⁸ are the same as defined above). } Is shown. ] The imidazoles represented by the formula [I-5] are halogenated in the presence of a halogenating agent. [In the formula, R ¹ , R ² , R ³ and Y are the same as defined above, and X ¹ represents a halogen atom. ] The manufacturing method of the phenyl imidazole derivative represented by these. 8. A compound represented by the general formula (I-7): [In the formula, R ¹ is a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, or 3 carbon atoms.
To a lower alkenyl group having 5 to 5 carbon atoms or a lower alkynyl group having 3 to 5 carbon atoms, R ² represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a haloalkyl group having 1 to 5 carbon atoms, and X represents It represents a hydrogen atom or a halogen atom, Y may be the same or different, represents a halogen atom, and R ^4-1 represents an alkyl group having 1 to 5 carbon atoms. ] The phenyl imidazole derivative represented by the following general formula (I-8) characterized by hydrolyzing [Wherein R ¹ , R ² , X and Y are the same as defined above. ] The manufacturing method of the phenyl imidazole derivative represented by these. 9. A compound represented by the general formula (I-9): [In the formula, R ¹ is a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, or 3 carbon atoms.
To a lower alkenyl group having 3 to 5 carbon atoms or a lower alkynyl group having 3 to 5 carbon atoms, R ² represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a haloalkyl group having 1 to 5 carbon atoms, and X represents A hydrogen atom or a halogen atom is shown, Y may be the same or different, a halogen atom is shown, and B is O, S or NH. And a phenylimidazole derivative represented by the general formula (VII): embedded image R ^4-2 -Hal (VIII) [wherein R ^4-2 is an alkyl group having 1 to 10 carbon atoms, or a carbon atom] A haloalkyl group having 1 to 5 carbon atoms, an alkenyl group having 3 to 5 carbon atoms, a lower alkynyl group having 3 to 5 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and -CH (R ⁵ ). COOR ⁶ (In the formula, R ⁵ represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, R ⁶ represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, An alkenyl group having 3 to 5 carbon atoms, a lower alkynyl group having 3 to 5 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkoxyalkyl group having 2 to 6 carbon atoms in total, or a sum indicates alkoxyalkoxyalkyl group of 3-9.) or embedded image ^{-CH (R 5) CON (R} 7) R 8 Wherein, R ⁵ is the same comb in the, R ⁷ and R ⁸ may be the same or different, represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, R ⁷ and R ⁸ together carbon It can also represent an alkylene group having 4 to 6 atoms), and Hal represents a halogen atom. ] The general formula (I-10) characterized by reacting a halide represented by [In the formula, R ¹ , R ² , R ^4-2 , X and Y are the same as defined above. ] The manufacturing method of the phenyl imidazole derivative represented by these. 10. A compound represented by the general formula (IX): [In the formula, R ¹ is a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, or 3 carbon atoms.
To a lower alkenyl group having 5 to 5 carbon atoms or a lower alkynyl group having 3 to 5 carbon atoms, R ² represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a haloalkyl group having 1 to 5 carbon atoms, and X represents It represents a hydrogen atom or a halogen atom, and Y's may be the same or different and represent a halogen atom. ] The general formula (I-13) characterized by oxidizing the imidazoles represented by [Wherein R ¹ , R ² , X and Y are the same as defined above. ] The manufacturing method of the phenyl imidazole derivative represented by these. 11. A compound represented by the general formula (I-13): [In the formula, R ¹ is a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, or 3 carbon atoms.
To a lower alkenyl group having 5 to 5 carbon atoms or a lower alkynyl group having 3 to 5 carbon atoms, R ² represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a haloalkyl group having 1 to 5 carbon atoms, and X represents It represents a hydrogen atom or a halogen atom, and Y's may be the same or different and represent a halogen atom. ] And a phenylimidazole derivative represented by the general formula (X): embedded image R ^9-1 -AH (X) [wherein A represents O or S, and R ^9-1 represents 1 or less carbon atoms] ~ 1
An alkyl group of 0, a haloalkyl group having 1 to 5 carbon atoms,
An alkenyl group having 3 to 5 carbon atoms, a lower alkynyl group having 3 to 5 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and -CH (R ⁵ ) CO-AR ¹⁰ (wherein R ⁵ and A are the same as above, R ¹⁰ is a hydrogen atom,
An alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, an alkenyl group having 3 to 5 carbon atoms, a lower alkynyl group having 3 to 5 carbon atoms, and 3 to 6 carbon atoms
Is a cycloalkyl group, an alkoxyalkyl group having a total number of carbon atoms of 2 to 6 or an alkoxyalkoxyalkyl group having a total number of carbon atoms of 3 to 9. ) Or embedded image —CH (R ⁵ ) CON (R ⁷ ) R ⁸ (in the formula, R ⁵ , R ⁷ and R ⁸ are the same as defined above). ] Or general formula (XI): embedded image R ^9-1 -Hal (XI) [In the formula, R ^9-1 is the same as defined above, and Hal represents a halogen atom. ] The compound of the general formula (I-14) characterized by reacting with a compound represented by [In the formula, R ¹ , R ² , R ^9-1 , X, Y and A are the same as defined above. ]
The manufacturing method of the phenyl imidazole derivative represented by these. 12. A compound represented by the general formula (I-15): [In the formula, R ¹ is a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, or 3 carbon atoms.
To a lower alkenyl group having 3 to 5 carbon atoms or a lower alkynyl group having 3 to 5 carbon atoms, X ¹ represents a halogen atom, Y may be the same or different, and represents a halogen atom, and R ³ is BR ⁴ {in the formula, B represents O, S or NH, R ⁴ represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, or an alkenyl having 3 to 5 carbon atoms. A group, a lower alkynyl group having 3 to 5 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, embedded image --CH (R ⁵ ) COOR ⁶ (in the formula, R ⁵ is a hydrogen atom or 1 carbon atom) indicates 5 alkyl group, R ⁶ is a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, an alkenyl group having 3 to 5 carbon atoms, 3 to 5 carbon atoms A lower alkynyl group, a cycloalkyl group having 3 to 6 carbon atoms, and a total number of carbon atoms of 2 to 6 An alkoxyalkyl group or an alkoxyalkoxyalkyl group having a total number of carbon atoms of 3 to 9) or embedded image --CH (R ⁵ ) CON (R ⁷ ) R ⁸ (wherein R ⁵ is the same as defined above) R ⁷ and R ⁸ may be the same or different and each represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and R ⁷ and R ⁸ together represent an alkylene group having 4 to 6 carbon atoms. Can also be shown.) } Or embedded image --CO-AR ⁹ {wherein A represents O or S, and R ⁹ represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, or carbon. An alkenyl group having 3 to 5 atoms, a lower alkynyl group having 3 to 5 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and -CH (R ⁵ ) CO-AR ¹⁰ (wherein R is ⁵ and A are the same as above, R ¹⁰ is a hydrogen atom,
An alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, an alkenyl group having 3 to 5 carbon atoms, a lower alkynyl group having 3 to 5 carbon atoms, and 3 to 6 carbon atoms
Is a cycloalkyl group, an alkoxyalkyl group having a total number of carbon atoms of 2 to 6 or an alkoxyalkoxyalkyl group having a total number of carbon atoms of 3 to 9. ) Or embedded image —CH (R ⁵ ) CON (R ⁷ ) R ⁸ (in the formula, R ⁵ , R ⁷ and R ⁸ are the same as defined above). } Is shown. ] The phenyl imidazole derivative represented by the formula [I-16] is characterized in that it is halogenated in the presence of a halogenating agent. [In the Formula, R < ¹ >, R < ³ >, X < ¹ > and Y are the same as the above, Z shows a halogen atom except a fluorine atom, p shows the integer of 1-3, q shows the integer of 0-2. . However, the sum of p and q is 3
And ] The manufacturing method of the phenyl imidazole derivative represented by these. 13. A compound represented by the general formula (I): [In the formula, R ¹ is a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, or 3 carbon atoms.
To a lower alkenyl group having 3 to 5 carbon atoms or a lower alkynyl group having 3 to 5 carbon atoms, R ² represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a haloalkyl group having 1 to 5 carbon atoms, and X represents A hydrogen atom or a halogen atom, Y may be the same or different, and a halogen atom, R ³ is: embedded image --BR ⁴ {in the formula, B represents O, S or NH, and R ⁴ is hydrogen; Atom, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 5 carbon atoms, alkenyl group having 3 to 5 carbon atoms, lower alkynyl group having 3 to 5 carbon atoms, and 3 to 6 carbon atoms A cycloalkyl group, -CH (R ⁵ ) COOR ⁶ (in the formula, R ⁵ represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, R ⁶ represents a hydrogen atom or 1 to 10 carbon atoms) An alkyl group, a haloalkyl group having 1 to 5 carbon atoms, an alkenyl group having 3 to 5 carbon atoms, Lower alkynyl group having 3 to 5 carbon atoms, cycloalkyl group having 3 to 6 carbon atoms, alkoxyalkyl group having 2 to 6 total carbon atoms, or alkoxyalkoxyalkyl group having 3 to 9 total carbon atoms Or --CH (R ⁵ ) CON (R ⁷ ) R ⁸ (wherein R ⁵ is the same as defined above, R ⁷ and R ⁸ may be the same or different, and a hydrogen atom or It represents an alkyl group having 1 to 6 carbon atoms, and R ⁷ and R ⁸ together may represent an alkylene group having 4 to 6 carbon atoms). } Or embedded image --CO-AR ⁹ {wherein A represents O or S, R ⁹ represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, or carbon. An alkenyl group having 3 to 5 atoms, a lower alkynyl group having 3 to 5 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and -CH (R ⁵ ) CO-AR ¹⁰ (wherein R is ⁵ and A are the same as above, R ¹⁰ is a hydrogen atom,
An alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, an alkenyl group having 3 to 5 carbon atoms, a lower alkynyl group having 3 to 5 carbon atoms, and 3 to 6 carbon atoms
Is a cycloalkyl group, an alkoxyalkyl group having a total number of carbon atoms of 2 to 6 or an alkoxyalkoxyalkyl group having a total number of carbon atoms of 3 to 9. ) Or embedded image —CH (R ⁵ ) CON (R ⁷ ) R ⁸ (in the formula, R ⁵ , R ⁷ and R ⁸ are the same as defined above). } Is shown. ] The herbicide which contains the phenyl imidazole derivative represented by these as an active ingredient. 14. A phenylimidazole derivative represented by the general formula (I), wherein R ¹ is hydrogen atom or 1 to 10 carbon atoms.
Represents an alkyl group having 1 to 5 carbon atoms, R ² represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a haloalkyl group having 1 to 5 carbon atoms, and X represents a hydrogen atom or halogen. An atom, Y may be the same or different, a halogen atom, R ³ is: embedded image --BR ⁴ (wherein B represents O, R ⁴ is a hydrogen atom, and has 1 to 10 carbon atoms).
An alkyl group having 10 carbon atoms, an alkenyl group having 3 to 5 carbon atoms,
Lower alkynyl group having 3 to 5 carbon atoms, 3 to 5 carbon atoms
Or a cycloalkyl group of 6 or —CH (R ⁵ ) COOR ⁶ (in the formula, R ⁵ represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, and R ⁶ has 1 to 10 carbon atoms). Alkyl group, haloalkyl group having 1 to 5 carbon atoms, cycloalkyl group having 3 to 6 carbon atoms, alkoxyalkyl group having 2 to 6 total carbon atoms, or alkoxyalkoxy having 3 to 9 total carbon atoms Represents an alkyl group). } Or embedded image --CO-AR ⁹ {in the formula, A represents 0, R ⁹ represents a hydrogen atom, or a carbon number of 1 to
An alkyl group having 10 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or -CH (R ⁵ ) CO-AR ¹⁰ (wherein R ⁵ and A are as described above). And R ¹⁰ is a hydrogen atom,
Alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 5 carbon atoms, cycloalkyl group having 3 to 6 carbon atoms, alkoxyalkyl group having 2 to 6 total carbon atoms, or total number of carbon atoms Represents an alkoxyalkoxyalkyl group of 3 to 9. ) Is shown. } Is shown. ] The herbicide of Claim 13 represented by these. 15. The phenylimidazole derivative represented by the general formula (I), wherein R ¹ represents a haloalkyl group having 1 to 5 carbon atoms, and R ² represents an alkyl group having 1 to 5 carbon atoms. , X represents a halogen atom, Y may be the same or different, and represents a halogen atom, R ³ is: embedded image --BR ⁴ {wherein B represents O, and R ⁴ has 1 to 10 carbon atoms. An alkyl group having 10 carbon atoms, an alkenyl group having 3 to 5 carbon atoms, a lower alkynyl group having 3 to 5 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or -CH (R ⁵ ) COOR ⁶ ( In the formula, R ⁵ represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, R ⁶ represents an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and the total number of carbon atoms. Represents an alkoxyalkyl group having 2 to 6 or an alkoxyalkoxyalkyl group having 3 to 9 carbon atoms in total. ) Shows the. } Or embedded image --CO-AR ⁹ {wherein A represents O, R ⁹ represents an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or CH (R ⁵ ) CO-AR ¹⁰ (In the formula, R ⁵ and A are the same as defined above, and R ¹⁰ is an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and the number of carbon atoms. Represents an alkoxyalkyl group having a sum of 2 to 6 or an alkoxyalkoxyalkyl group having a sum of carbon atoms of 3 to 9). } Is shown. ] The herbicide of Claim 14 represented by these. 16. A compound of the general formula (I) for protecting crops against unwanted weeds: [In the formula, R ¹ is a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, or 3 carbon atoms.
To a lower alkenyl group having 3 to 5 carbon atoms or a lower alkynyl group having 3 to 5 carbon atoms, R ² represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a haloalkyl group having 1 to 5 carbon atoms, and X represents A hydrogen atom or a halogen atom, Y may be the same or different, and a halogen atom, R ³ is: embedded image --BR ⁴ {wherein B represents O, S or NH, and R ⁴ represents hydrogen; Atom, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 5 carbon atoms, alkenyl group having 3 to 5 carbon atoms, lower alkynyl group having 3 to 5 carbon atoms, and 3 to 6 carbon atoms A cycloalkyl group, -CH (R ⁵ ) COOR ⁶ (wherein, R ⁵ represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, R ⁶ represents a hydrogen atom or 1 to 10 carbon atoms) An alkyl group, a haloalkyl group having 1 to 5 carbon atoms, an alkenyl group having 3 to 5 carbon atoms, Lower alkynyl group having 3 to 5 carbon atoms, cycloalkyl group having 3 to 6 carbon atoms, alkoxyalkyl group having 2 to 6 total carbon atoms, or alkoxyalkoxyalkyl group having 3 to 9 total carbon atoms Or --CH (R ⁵ ) CON (R ⁷ ) R ⁸ (In the formula, R ⁵ is the same as the above, R ⁷ and R ⁸ may be the same or different, and a hydrogen atom or It represents an alkyl group having 1 to 6 carbon atoms, and R ⁷ and R ⁸ together may represent an alkylene group having 4 to 6 carbon atoms). } Or embedded image --CO-AR ⁹ {wherein A represents O or S, R ⁹ represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, or carbon. An alkenyl group having 3 to 5 atoms, a lower alkynyl group having 3 to 5 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and -CH (R ⁵ ) CO-AR ¹⁰ (wherein R is ⁵ and A are the same as above, R ¹⁰ is a hydrogen atom,
An alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, an alkenyl group having 3 to 5 carbon atoms, a lower alkynyl group having 3 to 5 carbon atoms, and 3 to 6 carbon atoms
Is a cycloalkyl group, an alkoxyalkyl group having a total number of carbon atoms of 2 to 6 or an alkoxyalkoxyalkyl group having a total number of carbon atoms of 3 to 9. ) Or embedded image —CH (R ⁵ ) CON (R ⁷ ) R ⁸ (in the formula, R ⁵ , R ⁷ and R ⁸ are the same as defined above). } Is shown. ] The herbicidal method which applies the herbicide which uses the phenyl imidazole derivative represented by these as an active ingredient in 0.01g-10kg as an active ingredient amount per hectare, It is characterized by the above-mentioned. 17. A phenylimidazole derivative represented by the general formula (I), wherein R ¹ represents a haloalkyl group having 1 to 5 carbon atoms, and R ² represents an alkyl group having 1 to 5 carbon atoms. ,
X represents a halogen atom, Y may be the same or different, and represents a halogen atom, R ³ is -BR ⁴ (wherein B represents O, and R ⁴ has 1 to 10 carbon atoms). An alkyl group having 3 to 5 carbon atoms, an alkynyl group having 3 to 5 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or a —CH (R ⁵ ) COOR ⁶ (wherein , R ⁵ represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, R ⁶ represents an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and the total number of carbon atoms is 2 ~ 6 alkoxyalkyl group or an alkoxyalkoxyalkyl group having a total number of carbon atoms of 3 to 9). } Or embedded image --CO-AR ⁹ {wherein A represents 0, R ⁹ represents an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or CH (R ⁵ ) CO-AR ¹⁰ (In the formula, R ⁵ and A are the same as defined above, and R ¹⁰ is an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and the number of carbon atoms. Represents an alkoxyalkyl group having a sum of 2 to 6 or an alkoxyalkoxyalkyl group having a sum of carbon atoms of 3 to 9). } Is shown. ] The herbicidal method of Claim 16 represented by these.