JPH03151367A - 3-substituted phenylpyrazole derivative or its salt and use thereof - Google Patents

Abstract

NEW MATERIAL:A compound of formula [R<1> is alkyl; R<2> is haloalkyl; R<3> is halogen; R<4> is cyanoalkyl, cyanoalkenyl, dialkoxyphosphinylalkyl, 1,3-dioxolan-2- yl, C(R<5>)2-COR<6> (R<5> is H or alkyl; R<6> is OH, alkoxy or alkylthio), CH=N-OR<7> (R<7> is H, alkyl, alkenyl, etc.), CH=CH-COR<8> (R<8> is alkyl, alkoxy, etc.), etc.; X and Y are halogen) or a salt thereof. EXAMPLE:4-Chloro-3-(4-chloro-3-cyanomehyl-2-fluorophenyl)-5-diffuorome thoxy-1- methyl-1H-pyrazole. USE:A herhicide. PREPARATION:For example, a compound of formula II is reacted with a halogenating agent, subjected to a Sommelet reaction using hexamethylenetetramine and subsequently hydrolyzed with an acid to form a compound of formula III, which is reacted with hydroxylamine to provide the compound of formula I wherein R<4> is CH=N-OR<7> (R<7>=H).

Description

Detailed Description of the Invention The present invention relates to the general formula (1) [wherein R1 represents a lower alkyl group, R3 represents a myloalkoxy group, R3 represents a halogen atom, and R4
is a cyanoalkyl group, a cyanoalkenyl group, a lower dialkoxyphosphinyl alkyl group, a 1゜3-diok6noran-2-yl group, -C(R5), -COR6 (in the formula, R
s may be the same or different and represent a hydrogen atom or a lower alkyl group, and R6 represents a hydroxyl group, a lower alkoxy group or a lower alkylthio group. ), -CH-N-OR? (In the formula, R7 represents a hydrogen atom, a lower alkyl group, a lower alkenyl group, or a lower alkoxycarbonyl alkyl group.)
, -C)T=C)l-COR' (in the formula, R8 represents a lower alkyl group, lower alkoxy group or lower alkenyloxy group), -C)i, -A-R1 (in the formula, R9 is Represents a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower alkoxycarbonylalkyl group, or a lower acylalkylcarbonyl group, and A is oxygen COR
Mul (where RIO represents a hydroxyl group or a lower alkoxy group,
R11 represents a lower alkoxy group or a lower alganyloxy group. ), and X and Y may be the same or different and represent a halogen atom. The present invention relates to a 3-1i1 substituted phenyl pyrazole derivative represented by j or its salts, and a herbicide containing the compound as an active ingredient.

As a result of intensive research to create a new herbicide, the present inventors found that the 3-substituted phenylpyrazole derivative represented by formula t1) or its salts is a new compound that has not been described in any literature, and that it has a low The present invention was completed based on the discovery that it has a strong herbicidal effect on weeds at certain dosages.

As the prior art of the present invention, for example, Japanese Patent Laid-Open No. 50-117
No. 956, No. 52-91861, No. 54-70270
Although pyrazole-based compounds are disclosed in Japanese Patent Application Publication No. 55-9062, etc., the 3-substituted phenylpyrazole derivative represented by the general formula 11) or its salts of the present invention are not disclosed at all, and furthermore, this publication The 3-substituted phenylpyrazole derivatives or salts thereof of the invention have superior herbicidal effects at lower doses than the compounds described in these publications.

The 3-substituted phenylpyrazole derivative represented by the general formula (1) of the present invention or its salts has the structural isomers illustrated below, and these structural isomers are the 3-substituted phenylpyrazole derivative of the present invention or its salts. When salts are produced, they are produced simultaneously and can be produced by separating them using an appropriate separation method, such as recrystallization, column chromatography, etc., and the present invention also deals with these structural isomers. It is inclusive.

RL R
4(1) (1') (In the formula, R1, Rm, R3%R4, X & Y are the same as iC above.) As salts of the 3-substituted phenylpyrazole derivative represented by the general formula (1) of the present invention In addition to salts of mineral acids such as hydrochloric acid and sulfuric acid, salts of organic acids such as para-toluenesulfonic acid can be exemplified.

Represented by general formula (1) of the present invention! As a typical method for producing -flll-substituted phenylpiphenylpyrazole derivatives, for example, the production method illustrated below can be exemplified.

(ll-2) (1-1) 1 (1-2) (wherein, R11Hz, R'', X and Y are the same as above <L
,,R? -t represents a lower alkyl group, a lower alkenyl group, or a lower alkoxycarbonylalkyl group, 2 represents a halogen atom, and n and m represent an integer of 1 to 2, provided that the sum of n and m is 3. ) That is, by reacting the pyrazole represented by the general formula (II) with a halogenating agent in the presence of an inert solvent, -the formula (■-1
) is produced, and the pyrazole represented by the formula (It-
The pyrazole represented by 1) is isolated or not isolated, subjected to a Sommelet reaction with hexamethylenetetramine in the presence of an inert solvent, and further subjected to an acid hydrolysis reaction to obtain the formula (II-2). ) is produced, and then the pyrazole represented by the formula (n-2) is reacted with hydroxylamine or a salt thereof in the presence of an inert solvent and a base to produce the pyrazole represented by the general formula (I-
1), and then the 5-rl-substituted phenylpyrazole derivative represented by general formula (I-1) is converted into general formula (III-1) in the presence of an inert solvent and a base. A 3-substituted phenylpyrazole derivative represented by general formula (+-2) can be produced by reacting with a halide represented by 1).

A-1, - Formula (II) -> - General formula n-1) The inert solvent that can be used in this reaction may be any inert solvent that does not significantly inhibit the progress of this reaction, such as dichloromethane, chloroform, carbon tetrachloride. halogenated hydrocarbons such as benzene, toluene, xylene, etc., esters such as ethyl acetate, nitriles such as acetonitrile, benzonitrile, chain ethers such as methyl cellosolve, diethyl ether, dioxane , cyclic ethers such as tetrahydrofuran, sulfolane, dimethylsulfone, dimethylsulfoxide, and the like can be used, and these inert solvents can be used alone or in combination.

Examples of halogenating agents that can be used in this reaction include chlorine, bromine, N-prosuccinimide (NBS), N-chlorosuccinimide (NC5), tert-butyl hypohalite, trichloromethanesulfonyl halide, etc. halogenating agents can be used, NBS, NC3t
-I. When used as a rogogenating agent, it is preferable to use an organic peroxide such as benzoyl peroxide, etc. as a catalyst.

The amount of the halogenating agent to be used may be selected from the range of equimolar to excess molar relative to the pyrazole represented by the general formula (II).

The reaction temperature may be selected from the range of 0° C. to the boiling point of the inert solvent used.

The reaction time varies depending on the reaction scale, reaction temperature, etc., but may be selected from a range of several minutes to 48 hours.

After the reaction is completed, the reaction solution is evaporated by a conventional method such as distillation of the solvent,
By performing operations such as solvent extraction and producing tyI by recrystallization, column chromatography, etc. as necessary,
- It is possible to produce pyrazoles represented by the formula Cn-1).

A-2, -41 Formula (1-1) - + - General Formula II-2) This reaction consists of a Thumlett reaction as the first reaction and an acid hydrolysis reaction as the second reaction. As the solvent, for example, organic acids such as glacial acetic acid, mineral acids such as hydrochloric acid and sulfuric acid, water, etc. can be used alone or in combination.

The amount of hexamethylenetetramine used is according to the general formula (n-1)
It may be used in an equimolar amount to the 5-dl-substituted phenylpyrazole derivative represented by, but it can also be used in excess.

The reaction temperature may be selected from the range of 10°C to the boiling point of the inert solvent used, preferably in the range of 30 to 180°C.

After the reaction is completed, the reaction solution containing the target product may be subjected to a second reaction.

In the acid hydrolysis reaction, one reaction solution containing the target product obtained in the first reaction is used as it is, or if necessary, a large excess of hydrochloric acid,
The reaction may be carried out by adding a mineral acid such as sulfuric acid, preferably by adding a mineral acid such as hydrochloric acid.

The reaction temperature is selected in the range of 80°C to 180°C.

The reaction time varies depending on the reaction scale, reaction temperature, etc., but may be selected from a range of several minutes to 48 hours.

After the reaction is completed, by carrying out the same procedure as in A-1, -formula (
It is possible to produce pyrazoles represented by n-2).

A-5 - Formula (II-2) -> - General Formula 1-1) As the inert solvent that can be used in this reaction, for example, the inert solvent that can be used in A-1 can be used.

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 atoms or alkaline earth metal atoms such as sodium, potassium, magnesium, and calcium; carbonate or alcoholade, etc., and organic bases such as triethylamine, pyridine, 4-dimethylaminopyridine, 1,8-diazabicyclo(5+'*0]-7-
Organic bases such as undecene (DBU) can be used.

The amount of the base to be used may be selected from the range of equimolar to excess molar relative to the pyrazole represented by the formula (■-2).

Since this reaction is an equimolar reaction, it is sufficient to use equimolar amounts of each reactant, but hydroxylamine or its salts can also be used in excess relative to the pyrazole represented by general formula (II-2). .

The reaction temperature may be selected from the range of 0°C to 150°C, preferably from 10°C to 100°C.

The reaction time varies depending on the reaction scale, reaction temperature, etc., but can be selected from a range of several minutes to 48 hours.

After the reaction is completed, the general formula (1
A 3-substituted phenylvirazole derivative represented by -1) can be produced.

A-East General formula (I-1'') -> - General formula 1-2) As the inert solvent that can be used in this reaction, for example, the inert solvent that can be used in A-1 can be used.

As the base that can be used in this reaction, use the base that can be used in A-3 and proceed in the same manner as in A-3), the general formula (
A 5-@substituted phenylpyrazole derivative represented by I-2) can be produced.

(fl-2) (1-3) 1 (1-4) (In the formula, R1, RζR3, X and Y are the same as above < L
,, R9-1 represents an alkoxycarbonylalkyl group, and Z represents a halogen atom. ), that is, the general formula (II
-2) is reacted with a reducing agent in the presence of an inert solvent, -5-@ expressed by the formula (+-3)
A substituted phenylpyrazole derivative is prepared, and the general nuclear formula (I-
By isolating the 3-substituted phenylvirazole derivative represented by 3) or reacting it without isolation with a halide represented by general formula (III-2) in the presence of an inert solvent and a base. , a 3-&substituted phenylpyrazole derivative represented by the general formula (I-4) can be produced.

B-1, - Formula ([1-2) -> - General formula 1-5) Examples of inert solvents that can be used in this reaction are generally chain ethers such as dimethyl ether and diethyl ether;
Cyclic ethers such as dioxane can be used, but when using Na BI3 as a reducing agent, alcohols such as methanol, ethanol, and furopanol, dimethylformamide, dimethyl sulfoxide, diglyme, water, etc. should be used. These inert solvents can also be used alone or in combination.

Examples of the reducing agent include L i A1. H4, Na
A reducing agent such as BI3, NaBH4CN, etc. can be used, and the amount used may be selected from the range of 1/2 to excess mole relative to the pyrazole represented by the general formula (II-2).

The reaction temperature may be selected from the range of 0°C to the boiling point of the inert solvent used, preferably from 0°C to 100°C.

The reaction time varies depending on the reaction scale, reaction temperature, etc., but may be selected from a range of several minutes to 48 hours.

After the reaction is completed, the reaction solution is evaporated by a conventional method such as distillation of the solvent,
By performing operations such as solvent extraction and purifying by recrystallization, column chromatography, etc. as necessary, 5-i! represented by general formula (I-5) is obtained. phenylpyrazole derivatives can be produced.

B-2, General formula (I-5) → General formula (1-4) The inert solvent that can be used in this reaction may be any inert solvent that does not significantly inhibit the progress of this reaction, for example, the inert solvent used in A-1. Water can be used in addition to the inert solvent used. Moreover, when using a mixed solvent of water and an organic solvent insoluble in water, a phase transfer catalyst can also be used together with a base.

Since this reaction is an equimolar reaction, it is sufficient to use equimolar amounts of each reactant, and it is also possible to use an excess of the halide represented by formula (III-2).

As the base that can be used in this reaction, the base that can be used in A-5 can be used. The amount of the base to be used may be selected from the range of equimolar to excess molar relative to the 3-substituted phenylpyrazole derivative represented by general formula (I-5).

The reaction temperature may be selected from the range of 0°C to the boiling point of the inert solvent used, and is preferably carried out in the range of 0°C to 100°C. The reaction time varies depending on the reaction scale, reaction temperature, etc., but can range from several minutes to a few minutes. You can select from within 48 hours.

After the reaction is completed, the general formula (
A 3-substituted phenylpyrazole derivative represented by I-4) can be produced.

(In the formula, R1, R2, Rζ A% xl Y and Z are the same as above, M is a hydrogen atom or an alkali metal atom, and R1-x is a lower alkyl group, a lower alkenyl group,
Represents a lower alkynyl group, acylalkylcarboxyl group, or lower dialkoxyphosphinyl group, R 3 represents a lower alkyl group, lower alkenyl group, lower alkynyl group, or acylalkylcarbonyl group, and R←4 represents lower alkyl Indicates the group. ) That is, - a 3-substituted phenylpyrazole derivative represented by the formula (II-1'J) in the presence of an inert solvent and a base,
The compound represented by the general formula (I-3) or the formula (T[l
By reacting with the compound represented by -4), a 3-substituted phenylpyrazole derivative represented by general formula (I-5) can be produced.

This reaction can be carried out in the same manner as in 9-2 using the formula (1-5
) A 3-substituted phenylpyrazole derivative represented by:

Part (1-7) (wherein R1, R8, R3, X, Y and 2 are the same as above, R1-1 represents a lower alkyl group, and R2 represents a lower alkoxy group or a lower alkenyloxy group ) That is, - pyrazole represented by formula (n-2) and ketone represented by general formula (m-5) are reacted in the presence of an inert solvent and a base, or - formula A pyrazole represented by (n-2) and an acid anhydride are reacted in the presence of an inert solvent and a base, and 3-
producing substituted phenylvirazoles and then reacting with a no-logogenating agent in the presence or absence of an inert solvent,
-Producing acid I/rides represented by formula (II-3) and reacting nucleic acid halides with a compound represented by general formula (ill-/i) in the presence of an inert solvent and a base. Accordingly, 5-substituted phenylvirazoles represented by general formula (I-7) can be produced.

D-1, - Formula (n-2) -' - General formula 1-7) or General formula (I-6) This reaction may be carried out in the presence of an inert solvent, but preferably in the presence of an inert solvent. The acid anhydride used or - formula (m
It is preferable to use ketones represented by -4) as a solvent.

As the base that can be used in this reaction, for example, an alkali metal salt of an organic acid such as sodium acetate, an inorganic base such as hydroxide, etc. can be used, and the amount of the base to be used is determined according to the general formula (II-2). The catalytic amount can be selected from the range of equimolar to excess molar relative to the pyrazole represented by, and it is preferably used in slight excess.

The reaction temperature may be selected from room temperature to the boiling point of the inert solvent used, preferably from 30 to 200°C.

The reaction time varies depending on the reaction amount, reaction temperature, etc., but is in the range of several minutes to 48 hours.

After the reaction is completed, by carrying out the same procedure as in B-2, - formula (
t-6) or -3-substituted phenylpyrazole derivatives represented by the formula C1-7> can be produced.

D-2, general formula (I-6) - + - general formula! I-1 Examples of inert solvents that can be used in this reaction include t td halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride, aromatic hydrocarbons such as benzene, toluene, and xylene, methyl cellosolve, and diethyl. Chain ethers such as ether and diisopropyl ether, and cyclic ethers such as dioxane and tetrahalodofuran can be used. ) ~ As the rogening agent, for example, thionyl chloride, phosphorus trichloride, phosphorus pentachloride, etc. can be used.

The amount of halogenating agent used is expressed by general formula (1-6) 3
The amount may be selected from the range of equimole to excess mole relative to the -substituted phenylpyrazole derivative, and it is preferable to use an excess amount.

The reaction temperature may be selected from room temperature to the boiling point of the inert solvent used.

The reaction time varies depending on the reaction amount, reaction temperature, etc., but is in the range of several minutes to 48 hours.

After the reaction is completed, by applying pressure in the same manner as in B-2, - formula (
Acid halides represented by n-3) can be produced.

D-5 - Formula (n-1 → General formula (I-7)) In this reaction, it is sufficient to react with an excess amount of alcohol corresponding to the desired ester; in this case, the alcohol acts as an inert solvent. It is also something to do.

It is also possible to react with an alcohol corresponding to the ester in the presence of an inert solvent and a base. As the inert solvent that can be used in this case, for example, an inert solvent that can be used in acid halide formation can be used, and the amount of alcohol used may be equimolar to excess molar.

As the base that can be used in this reaction, for example, the base that can be used in A-3 can be used.

The reaction temperature may be selected from the range of 0°C to the boiling point of the inert solution used, preferably from 0°C to 150°C.

The reaction time varies depending on the reaction amount, reaction temperature, etc., but is in the range of several minutes to 48 hours.

After the reaction is completed, a 3-[substituted phenylpyrazole derivative represented by general formula (I-7)] can be produced by carrying out the same procedure as in B-2.

(II-1') (1-8) (1-9) (In the formula, Rt%Ha, R3, M, X%Y and ZFi Same as above, R←1 represents a lower alkyl group or a lower alkenyl group and R4-2 represents a hydrogen atom, a lower alkyl group, or a lower alkenyl group.) (1-8) 3
-11 is substituted to produce a phenylpyrazole derivative, and further the 3-substituted phenylpyrazole derivative represented by the general formula (I-8) is combined with a halide represented by the general formula (1-7), an inert solvent, and a base. By reacting in the presence of, a 3-substituted phenylpyrazole derivative represented by general formula (I-9) can be produced.

E-1, - Formula Cu-1') → - General formula 1-8) This reaction is carried out in the same manner as B-2 to produce a 5-substituted phenylpyrazole derivative represented by formula (1-8). can do.

E-Z General formula (I-8) - + - General formula 1-9) This reaction is carried out in the same manner as in A-4 to form -f formula (1-9)
A 3-substituted phenylpyrazole derivative represented by can be produced.

1 (1-8) 1 (1-10) 1 (1-11) 1 (II-4) 1 ([-12) (wherein, R1, R1, R3, R5, X, Y and Z l
d Same as above, R@=1 represents a lower alkoxy group or a lower alkylthio group. ) That is, 3- expressed by general formula (1-8) obtained by E method
The substituted phenylpyrazole derivative was alkylated with an alkylating agent in the presence of an inert solvent and a base to form the general formula (I-1
0) is produced, and then the 3-substituted phenylpyrazole derivative represented by general formula (I-10) is subjected to a hydrolysis reaction in the presence of a mineral acid such as hydrochloric acid or sulfuric acid. to produce 5-substituted phenylpyrazoles represented by general formula (I-11), and further 3-substituted phenylpyrazoles represented by general formula (I-11) in the presence of an inert solvent. or in the absence of a halogenating agent to produce an acid halide represented by the formula (■-4), and react the nucleic acid halide with the general formula (III-8) in the presence of an inert solvent and a base. ) A 3-substituted phenylvirazorro represented by general formula (I-12) can be produced by reacting with a compound represented by formula (I-12).

F-1, general formula (I-8) → - general formula 1-10) In addition to the inert solvent that can be used in A-1, examples of inert solvents that can be used in this reaction include dimethylformamide, hexamethylphosphoric Inert solvents such as triamides can be used.

As the base that can be used in this reaction, in addition to inorganic bases such as sodium hydride, potassium hydroxide, and sodium hydroxide, alcoholades such as potassium tert-butoxide can be used.

The amount of the base to be used is based on the 3-substituted phenylpyrazole derivative represented by the general formula (1-8), -the formula (f-10)
Depending on the number of substitutions of R5 in the 3-substituted phenylpyrazole derivative represented by the formula, it can be selected from a range of equimolar to around twice the molar.

Since this reaction is an equimolar reaction, it is sufficient to use equimolar amounts of each reactant, but the alkylation Just choose the amount of agent.

The reaction temperature may be selected from the range of 0°C to the boiling point of the inert solvent used, preferably 1ltO to 150°C.

The reaction time varies depending on the reaction amount, reaction temperature, etc., but is in the range of several minutes to 48 hours.

After the reaction is completed, the general formula (
A 3-substituted phenylpyrazole derivative represented by I-10) can be produced.

F-2, general formula (I-10) -> - general formula l-11) In this reaction, an acid hydrolysis reaction may be carried out using an aqueous solution of a mineral acid such as hydrochloric acid or sulfuric acid as an inert solvent and a reactant.

The reaction temperature may be selected from the range of 80°C to 250°C, preferably within the range of 80°C to 200°C.

The reaction time varies depending on the reaction amount, reaction temperature, etc., but is in the range of several minutes to 48 hours.

After the reaction is complete, pour the reaction solution containing the target product into ice water, filter the precipitate, or isolate the target product by solvent extraction, etc., and if necessary, purify it by recrystallization, column chromatography, etc. Therefore, 3- represented by the general formula (I-)
Substituted phenylpyrazole derivatives can be prepared.

F-5 General formula (I-11) → -General formula II-4) By carrying out this reaction in the same manner as D-2, -Math formula (II-4)
) can be produced.

F-4-Formula (na)-+-ff Formula (1-1z) General formula (I-12
) A 3-substituted phenylpyrazole derivative represented by:

(1-12') (1-13) (1-14) (In the formula, R1, R, R3, R11, x%y and zh are the same as above, <L, and R10-t represents a lower alkoxy group.

) That is, a 3-substituted phenylpyrazole derivative represented by the general formula (1-12') obtained by method F is reacted with an alkyl formate such as methyl formate in the presence of an inert solvent and a base to obtain the general formula ( A 3-substituted phenylpyrazole derivative represented by I-15) is produced, and then the general formula (I-15)
By reacting the 3-substituted phenylpyrazole derivative represented by formula (I-13) with a halide represented by formula (m-9) in the presence of an inert solvent and a base,
) A 3-substituted phenylpyrazole derivative represented by:

G-1, - Formula <1-12') → - General formula 1-13) This reaction is carried out in the same manner as the production method of F-1, for example, to produce 3- represented by the general formula (I-13). Substituted phenylpyrazole derivatives can be prepared.

G-1 General formula (I-13) -> - General formula 1-14) This reaction can be carried out, for example, in the same manner as the production method of A-4,
A 3-substituted phenylpyrazole derivative represented by general formula (I-14) can be produced.

(n-2) (1-15) (In the formula, R1, RζR3, By reacting with 1,2-ethanediol, 3-
Substituted phenylpyrazole derivatives can be prepared.

Examples of inert solvents that can be used in this reaction include D-2
Examples include inert solvents that can be used in the production method.

As catalysts that can be conveniently used in this reaction, acidic catalysts or dehydrating agents can be used, such as hydrochloric acid, sulfuric acid, para-toluenesulfonic acid, phosphoric acid, ion exchange resins, silica gel, molecular sieves, etc. Preferably, p-toluenesulfonic acid is used for azeotropic dehydration, and the amount of catalyst used is determined from the range of equimole based on the catalyst amount to the pyrazole represented by general formula (n-2). The pyrazole and 1,2-ethanediol may be used in equimolar amounts, and 1,2-ethanediol may be used in excess.

The reaction temperature may be selected from the range of 0°C to the boiling point of the inert solvent used, preferably from 30°C to 200°C.

The reaction time varies depending on the reaction amount and reaction temperature, but is in the range of several minutes to 48 hours.

After the reaction is completed, the general formula (
A 3-substituted phenylpyrazole derivative represented by I-15) can be produced.

CI) Salts Examples of the salts of the 3-!! substituted phenylpyrazole visiting conductor represented by the general formula (υ) of the present invention include salts of mineral acids such as hydrochloric acid and sulfuric acid, as well as organic acids such as para-toluenesulfonic acid. These salts can be obtained by treating the 3-substituted phenylpyrazole derivative represented by the general formula (1) produced by the production method of A-H with a mineral acid, an organic acid, etc. , salts of the 3-substituted phenylpyrazole derivative represented by the general formula (I) can be produced.

Below, representative compounds of the 3-substituted phenylpyrazole derivatives or salts thereof represented by the general formula (i) of the present invention are listed below.
Although illustrated in the table, the present invention is not limited to these compounds.

General formula (I) No. 1 In the table, The physical properties are described as crystalline or oily. The NMR data of the compounds obtained are shown in Table 2.

-Representatives of pyrazoles represented by formula (II), which are raw material compounds for producing 1A of the 3-substituted heptadylvirazol derivative represented by general formula (1) or its salts of the present invention Examples of the manufacturing method include the manufacturing method illustrated below (Vl) (■) 1 (■n (where R1, Rz%Rs,
i Same as above 1, R represents a haloalkyl group. ) i.e.
- A compound represented by the formula (slash) is reacted with diethyl carbonate to produce a compound represented by the formula (■), and then the compound (■) and the compound represented by the formula (■) are dorazine - to produce pyrazoles represented by the formula (Vl), and further to react the pyrazoles represented by the - formula (■) with halides represented by the general formula (V), - A pyrazole represented by the formula (IV) is produced, and the - formula (
By halogenating the pyrazole represented by IV), a pyrazole represented by the formula -to+ can be produced.

Typical examples of the 3-substituted phenyl pyrazole derivative represented by general formula (1) or salts thereof of the present invention are shown below, but the present invention is not limited thereto.

Example 1゜1-1. 5-(5-bromomethyl-4-chloro-2-
1) Production of 1-pyrazole 4-chloro-3-(4-chloro-2-fluoro-5-methylphenyl)-5-difluoromethoxy -1-Methyl-1H-pyrazole&9? (20 mmol) was suspended in 100 d of carbon tetrachloride, and N-bromide succinimide 197
f (22 mmol) and a catalytic amount of benzoyl peroxide were added, and the reaction was carried out under reflux for 5 hours. After completion of the reaction, insoluble matter in the reaction solution was filtered off, the filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography to obtain the target product 569t.
was obtained as a viscous substance.

Physical properties: viscous material Yield: 62% NMR (δ value, CDCl3/TMS, ppm
)583 (3M, s), 4.53 (2H, s), A67
(IH, t.

J=72Hz), 7.22(11(,d, J=10Hz
), 7.60 (IH, d, J=8Hz).

-2-4-Chloro-3-(4-chloro-5-cyanmethyl-2-fluorophenyl)-5-difluoromethoxy-1-methyl-IH-pyrazole production (Compound Shop 1)
.

5-(5-bromomethyl-4-chloro-2-fluorophenyl)-4-chloro-5-Schiff A/olomethoxy-
1-Methyl-1H-pyrazole 2,09 (4,8 mmol) was dissolved in isopropyl alcohol 151,
This solution was dropped into an aqueous solution IIL3- containing sodium cyanide 129f (&0 mmol) at room temperature over 40 minutes.

After the dropwise addition was completed, the reaction was further carried out at room temperature for 1 hour.

After the reaction, the isopropyl alcohol was distilled off under reduced pressure, water was added to the residue, the target product was extracted with ethyl acetate, the extract was washed with water, and after drying, the solvent was distilled off under reduced pressure, and the residue was subjected to column chromatography. Purification by graphography yielded the target product 1411.
was obtained as a crystal.

Physical properties: m, p, 8a5°C Yield: 804 Example 2 2-1.2-chloro-5-(4-chloro-5-fudifluoromethoxy-1-methyl-1)1-hyrasol-3-
Preparation of yl)-4-fluorobenzaldehyde CH, CH.

4-chloro-3-(4-chloro-5-dibromomethyl-
2-fluorophenyl)-5-difluoromethoxy-1
-Methyl-1H-pyrazole 14.49 (50 mmol) was clouded with 50w1K of concentrated hydrochloric acid and reacted under reflux for 5 hours. After the reaction was completed, the reaction mixture was poured into ice water, the target product was extracted with ethyl acetate, the extract was washed with a 50% aqueous sodium bicarbonate solution, washed with water, dried, concentrated under reduced pressure, and the residue was filtered into a column. The desired product &Or was obtained by chromatography.

Physical properties: m, p, 107.5°C Yield 59 2-
2. 4-chloro-3-(4-chloro-2-fluoro-
Preparation of (5-hydroxymethylphenyl)-5-difluoromethoxy-1-methyl-1H-pyrazole (compound 18) CH,C)I.

2-chloro-5-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)-4-
Fluorobenzaldehyde (L 69 (1.7 mmol) was dissolved in 10 d of absolute ethanol, sodium borohydride 006 f (t7 mm+) mol) was added to the solution, the reaction was carried out at room temperature for 1 hour, and then further Sodium borohydride α06f (1.7 mmol) was added to carry out the reaction. After the reaction is complete, the reaction solution is poured into water and made acidic with dilute hydrochloric acid.The target product is extracted with ethyl acetate.The extract is washed with water, dried, and the solvent is distilled off under reduced pressure.The resulting residue is applied to a column. Purify by chromatography to obtain the target substance a56? was obtained as a crystal.

Physical properties: Kame p, 99.1°C Yield: 93 Example 5 2
-[2-chloro-5-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl]-
Production of ethyl 4-fluorobenzyloxypropionate (compound 10) 4-chloro-3-(j-chloro-2-fluoro-5-hydroxymethylphenyl)-5-difluoromethoxy-
1-Methyl-1H-pyrazole (150? (1.4 mmol)) was dissolved in acetone, and the solution was mixed with potassium carbonate α409 (2.9 mmol), ethyl α-bromopropionate (56 mmol), mmol) was added, and the reaction was carried out under reflux for 3 hours. After the reaction was completed, the reaction solution was poured into water, the second target product was extracted with ethyl acetate, and the extract was washed with water.
After drying, the solvent was distilled off under reduced pressure, and the resulting residue was purified by column chromatography to obtain the target product r:L25f as an oil.

Physical properties: nOt526G (211°C) Yield 239% Example 42-chloro-5-(4-chloro-5-difluoromethoxy-1-methyl-IH-pyrazol-3-yl)
-Production of 4-fluorophenyl acetic acid (compound S12) CHs CHs4-
1.1Of (50 mmol) of chloro-3-(4-chloro-5-cyanomethyl-2-fluorophenyl)-5-difluoromethoxy-1-methyl-1H-pyrazole was added to 5
The mixture was suspended in a 0% aqueous sulfuric acid solution and reacted for 15 minutes under reflux. After the reaction is complete, the reaction solution is poured into water, the target product is extracted with ethyl acetate, the extract is washed with water, dried, the solvent is distilled off under reduced pressure, and the resulting residue is recrystallized with ethyl acetate to obtain the target product. 1. Of was obtained as a crystalline product.

Physical properties: 162.9°C Yield: 89 Excellent Example 5-2-chloro-5-(4-chloro-5-difluoromethoxy-1-methyl-1)1-pyrazole-3-
Production of (compound 419) CH32-chloro-5-(4-chloro-5-difluoromethoxy-1
-Methyl-1H-pyrazole-3-(l)-4-fluorobenzaldehyde α70f (2-0 mmol), acetic anhydride 10d1 sodium acetate α25t (50 mmol)
The reaction was carried out for 10 hours while the parent solution was refluxed. After the reaction is complete, the reaction solution is poured into water and the target product is extracted with ethyl acetate.
After washing the extract with water and drying, the solvent was distilled off under reduced pressure, and the resulting residue was recrystallized to obtain the target product α612 as a crystal.

Physical properties: Crystalline Yield: 8011 Examples & [2-chloro-5-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazole-3-
2-chloro-5(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)-4-fluorobenzaldehyde 1 .411 (4.1 mmol)
was dissolved in 2 d of ethanol, and hydroxylamine hydrochloride (137 t (5.4 mmol)) was added to water [1
A solution containing 6yxlK fg was added dropwise at room temperature.

After the dropwise addition was completed, a solution of sodium hydroxide α24 (5.4 mmol) in water [16aj] was further added dropwise to the reaction solution, and after the dropwise addition was completed, the reaction was carried out at room temperature for 2 hours. After the reaction was completed, the reaction solution was poured into water, the target product was extracted with ethyl acetate, the extract was washed with water, and after drying, the solvent was distilled off under reduced pressure, and the resulting residue was recrystallized to obtain the target product [164r' Obtained as a crystalline product.

Physical properties: Kame p, 147.1°C Yield: 444 Example 7.2-(2-chloro-5-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)-4 -Fluorophenylmethyleneazanyloxy]
Production of ethyl propionate (Kakaimonoya 30) [2-chloro-5-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)-4
-Fluorophenylmethylene]Azanol α202 (α
Potassium carbonate (L159 (1.1 mmol), α
-Ethyl bromopropionate α2C1 (1.1 mmol) was added, and the reaction was carried out under reflux for 3 hours. After the reaction is complete,
The reaction solution was poured into water, the target product was extracted with ethyl acetate, the extract was washed with water, dried, and the solvent was distilled off under reduced pressure. The resulting residue was purified by column chromatography to obtain the target product (L
18f was obtained as an oil.

Physical properties: nD 1.5354 (21.9°C) Yield nia 04 The 3-substituted phenylpyrazole derivative represented by the general formula (1) of the present invention or its salt @ can be used, for example, for Family: Annual grasses, typical harmful grasses of paddy fields)
, Cyperaceae (Cyperaceae - annual grass, harmful grass of rice fields), Pine snail (Cyperaceae - perennial grass, wetlands, waterways,
A common perennial harmful grass that occurs in paddy fields, a typical harmful perennial grass of rice fields), Urikawa (a perennial harmful grass of the family Cyperaceae that occurs in wetlands, ditches, and rice fields), firefly (a perennial grass of the family Cyperaceae, that occurs in wetlands, waterways, and rice fields), oats (a perennial harmful grass of the family Cyperaceae, common in wetlands, waterways, and rice fields), Perennial grasses of the Poaceae family, occurring in fields and fields), Poaceae (Poaceae - a typical harmful grass of annual grasses, fields and orchards), Gishigishi (perennial grasses of the Polygonaceae family, occurring in fields and roadsides), Cyperaceae (Cyperaceae -) annual grass, upland,
(Occurs on roadsides), Aobi (Family: annual grass, occurs on fields, roadsides, walls), Yaemugura (Rubiaceae: annual grass, severely harmful grass on fields), Psyllium (Rubiaceae, annual grass, in fields,
Harmful grasses in orchards), Chamomile (Asteraceae, Harmful grasses in fields)
, Ichito (Malvaceae, a severely harmful grass in the fields), Onna fir (Asteraceae - an annual grass, a severely harmful grass in the fields), Paddy morning glory (Convolvulaceae, a severely harmful grass in the fields), etc. in rice fields, fields, and trees. , has the effect of controlling annual grasses and perennial weeds that occur in wetlands, etc.

Since the 3-substituted phenylpyrazole derivative represented by the general formula (1) or its salts of the present invention exhibits an excellent control effect against weeds before and after emergence, the infestation of useful plants is expected. The herbicide of the present invention can be treated by treating the ground in advance or after the planting of useful plants (including cases where useful plants have already been planted in gardens) from the beginning of weed emergence to the growing season. Characteristic physiological activities can be effectively expressed.

However, the herbicide of the present invention does not have to be used only in this manner; for example, the herbicide of the present invention can not only be used as a herbicide for paddy fields or fields, but also as a herbicide for general weeds. It can also be used, for example, on mowing marks, fallow fields, ridges,
Farm roads, waterways, pasture land, cemeteries, parks, roads, playgrounds,
It can also be used to exterminate general weeds in vacant lots, cultivated areas, railroad tracks, forests, etc. around buildings. In this case, it is economically most effective to treat the weeds before they begin to emerge, but this is not necessarily the case, and it is possible to control weeds during the growing season.

5-I! represented by the general formula t1) of the present invention! When phenylpyrazole derivatives or salts thereof are used as herbicides, they are generally formulated into a form convenient for use according to conventional methods for agricultural chemical formulations.

That is, the 3-substituted phenylpyrazole derivative represented by the general formula (f) of the present invention or its salts can be blended in an appropriate proportion with an appropriate inert carrier or with an auxiliary agent if necessary. It may be used by dissolving, separating, suspending, mixing, impregnating, adsorbing, or adhering it to an appropriate dosage form, such as a suspension, emulsion, liquid, aqueous preparation, granule, powder, or tablet. .

The inert carrier that can be used in moxibustion may be either solid or liquid. Materials that can be used as solid carriers include, for example, soybean flour, grain flour, wood flour, bark powder, saw powder, and tobacco stem powder. Flour, walnut flour, bran, cellulose powder, residue after extracting plant extracts, synthetic polymers such as crushed resin, clays (e.g. kaolin, bentonite, acid clay, etc.), talcs (e.g. talc, pyrophyllite, etc.), Silicas (
For example, diatomaceous earth, silica sand, mica, white carbon (highly dispersed silicic acid also known as hydrated fine powder silicon or hydrated silicic acid, and some products contain calcium silicate as a main component).

]), activated carbon, sulfur powder, pumice, calcined diatomaceous earth, crushed bricks, fly ash, sand, inorganic mineral powders such as calcium carbonate and calcium phosphate, chemical fertilizers such as ammonium sulfate, ammonium phosphorus, ammonium nitrate, urea, ammonium chloride, etc. Compost etc. can be mentioned.

These may be used alone or in the form of a mixture of two or more.

Materials that can serve as liquid carriers are selected from those that themselves have solvent ability, as well as those that have solvent ability but can disperse the active ingredient compound with the help of adjuvants, such as typical examples. Examples of carriers include the following, which may be used alone or in the form of a mixture of two or more, such as water, alcohols (e.g. methanol, ethanol, isopropanol, butanol, ethylene glycol, etc.), Ketones (e.g. acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, etc.), ethers (e.g. ethyl ether, dioxane, cellosolve, dipropyl ether, tetrahydrofuran, etc.), aliphatic hydrocarbons (e.g. gasoline, mineral oil, etc.) , aromatic hydrocarbons (e.g. benzene, toluene, xylene, solvent naphtha,
(alkylnaphthalene, etc.), halogenated hydrocarbons (e.g., dichloroethane, chloroform, carbon tetrachloride, etc.), esters (e.g., ethyl acetate, diisopropyl phthalate, dibutyl phthalate, dioctyl phthalate, etc.),
Examples include amides (eg, dimethylformamide, diethylformamide, dimethylacetamide, etc.), nitriles (eg, acetonyl, IJ, etc.), dimethylsulfoxide, and the like.

Other adjuvants include the following typical adjuvants, and these adjuvants are used depending on the purpose, and in some cases, two or more adjuvants are used in combination. It is also possible in some cases to use no adjuvant at all.

Surfactants are used for the purpose of emulsifying, dispersing, dissolving and/or wetting the active ingredient compounds, such as polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, polyoxyethylene higher fatty acid ester, polyoxyethylene Examples of surfactants include resin acid esters, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monooleate, alkylaryl sulfonates, naphthalene sulfonic acid condensates, lignin sulfonates, and higher alcohol sulfate esters. Can be done.

In addition, for the purpose of dispersion stabilization, adhesion and/or binding of the active ingredient compound, the following auxiliary agents may be used, such as casein, gelatin, starch, methyl cellulose, carboxymethyl cellulose, gum arabic, and polyvinyl alcohol. , pine oil, bran oil, bentonite, lignin sulfonate and the like may also be used.

The following auxiliaries can also be used to improve the flowability of solid products, for example auxiliaries such as waxes, stearates, phosphoric acid alkyl esters, etc.

Auxiliary agents such as naphthalene sulfonic acid condensates, condensed phosphates, etc. can also be used as peptizers for suspension products.

As the antifoaming agent, auxiliary agents such as silicone oil can also be used.

Distribution of active ingredient compounds 4! r can be adjusted as necessary; for example, when making powder or granules, it is 110
A weight ratio of 1 to 50 is suitable, and a range of 101 to 50 by weight is similarly suitable when used as an emulsion or an irrigation agent.

The herbicide of the present invention containing a 5-substituted phenylpyrazole derivative represented by the general formula (i) or a salt thereof as an active ingredient is
In order to kill or suppress the growth of various weeds, administer an amount effective for killing or suppressing the growth of weeds, either as is, diluted with water, etc., or suspended in a round form in an effective amount to kill or suppress the growth of the weeds. Or, in places where growth is unfavorable, it can be applied to foliage or soil.

The amount of the herbicide containing the 3-substituted phenylpyrazole derivative represented by the general formula (1) of the present invention or its salt as an active ingredient is determined by various factors, such as the purpose, target weeds, weeds, etc. Although it varies depending on the occurrence/growth situation, weed emergence tendency, weather, environmental conditions, dosage form, application method, application place, application time, etc., the amount of active ingredient compound per hectare [L12
It may be selected appropriately from the range of 5 to 5 square meters depending on the purpose.

When using the herbicide containing the 5-[substituted phenylpyrazole derivative or its salts represented by the general formula (1) of the present invention as an herbicide for paddy fields or upland fields, for example, the amount of the active ingredient is It is sufficient to select a dosage of 1002 or less per 1,000 ml, which does not cause phytotoxicity to crops and can selectively control the target weeds.When using as a herbicide for non-agricultural land, The amount of active ingredient should be selected to be 1002 or more per hectare, which can kill the target weeds.

The herbicide containing the 3-substituted phenylpyrazole conductor or its salts represented by the general formula (+1) of the present invention as an active ingredient is used to further control target herb species, expand the appropriate period for control, or reduce the dosage. It can also be used in combination with other herbicides.

Typical test examples and formulation examples of the composition of the present invention are illustrated below. In addition, in the prescription examples, parts indicate parts by weight.

Test Example t Unveiling effect on paddy rice weeds after germination 1/10,000 R pots were filled with soil @ gold to create a paddy field condition, and paddy field weeds such as Novie, Seeds of Firefly, and Tubers of Cyperus japonica and Urikawa were adjusted to the single-leaf stage. This was treated with a spray solution of the present invention (formula &'e) shown in Table 1 as an active ingredient. Processing 21
After a few days, the herbicidal effect was investigated, and the herbicidal rate was calculated by comparing it with no treatment, and the evaluation was made according to the following criteria. At the same time, phytotoxicity to paddy rice was investigated and phytotoxicity was determined according to the following criteria.

Criteria for determining herbicidal activity 5...More than 954 weeds killed 4...More than 70 weeds less than 954 3... More than 50 regrets and less than 70 people killing grass 2...304 or more and less than 50 weeds 1...More than 10 and less than 50 weeds 0...Less than 10% weed killing Judgment criteria for drug damage 0...No drug damage.

1... Browning occurs, but it recovers in the early stage and there is almost no growth inhibition.

2...Clear growth suppression is observed along with browning, but recovery occurs at an early stage.

5... Browning and growth inhibition are significant, and recovery is slow.

4... Significant browning and growth suppression, with some individuals even dying.

5... Almost all individuals die.

The results are shown in Table 3.

Table 3 Comparison Compound A is the 3-phenyl-5-methylthiopyrazole described on page 5 of JP-A-52-91861, B is the compound described in Example 1 on page 4 of the same publication, C A8 described in JP-A-54-70270, and D
Compound Ya 159 described on page 9 of JP-A-55-9062 was used as a comparative compound.

Compound A, Compound B.

Compound C1 Compound.

As shown in Table 5, 5 represented by the general formula (1) of the present invention
-1Ili-converted pyrazole derivatives or their salts have a strong herbicidal effect on each weed tested in post-emergence treatment at an active ingredient dose of 7tr 514F per hectare, but against rice. It also causes drug damage. However, by further reducing the dosage, the desired herbicidal effect can be maintained,
Chemical damage to rice is reduced.

Test Example 2 Vertical IQc of herbicidal effect on field weeds before emergence
Soil was packed into a polyethylene cracked vat measuring m x width 2 Q cm x height 5 ann, and seeds of upland weeds such as field weeds such as Japanese field weed, Japanese croaker, Japanese grasshopper, and field weed, as well as field crops such as soybean and wheat, were sown and covered with soil.

This was treated with a spray solution containing a compound of the present invention (compounds listed in Table 1) at a predetermined concentration as an active ingredient. Processing 1
After 4 days, the herbicidal effect was investigated, and the herbicidal rate was calculated and judged in the same manner as Test Example 1. At the same time, phytotoxicity to soybeans and wheat was investigated, and phytotoxicity was determined according to the standards of Test Example 1.

The results are shown in Table 4.

Table 4 As shown in Table 4, 5 expressed by the general formula +1) of the present invention
The -vt-converted phenylpyrazole derivative or its salts exhibits a strong herbicidal effect on each test weed when treated before emergence in the field at an active ingredient dose of 5 kg per hectare;
It also causes phytotoxicity to wheat and soybeans, but by further reducing the dosage, the desired herbicidal effect can be maintained and the phytotoxicity to wheat and soybeans can be reduced.

Test Example 5 Herbicidal effect on field weeds after emergence Vertical 105
1 x horizontal 20. Fill a polyethylene vat with a height of 5α with soil, and sow and cover the field noxious weeds, wheat, and wheat seeds listed below, as well as dice and wheat seeds as field crops, until each reaches the leaf stage shown below. The plants were allowed to grow and treated with the compound of the present invention (compounds listed in Table 1) as an active ingredient as a spray solution at a predetermined concentration. The herbicidal effect was investigated 21 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 dice and wheat was investigated, and phytotoxicity was determined according to the standards of Test Example 1.

Test weed species and their leaf stages, and the leaf stage of evening grass and wheat, 2-leaf stage Ichibi, 2-leaf stage Ichibi, 1-leaf stage Prunus chinensis.
1s period Yaemugura
Two-leaf stage wheat Two-leaf soybean One-leaf stage results are shown in Table 5.

Table 5 As shown in Table 5, 3 represented by the general formula (1) of the present invention
-Substituted phenylpyrazole derivatives or their salts have a strong herbicidal effect on various test weeds in post-emergence treatment in the field at a dose of 5 tons per hectare of active ingredient, but they are also harmful to wheat and soybeans. occurs. However, by further reducing the dosage, the desired herbicidal effect can be maintained, and wheat,
The chemical damage to dice is reduced.

Formulation Example 1 Compound Product 1 50 parts Polyoxyethylene nonylphenyl ether 5 parts or more are uniformly mixed and pulverized to prepare a wettable powder.

Formulation Example Z Compound/fL5 5 parts Bentonite clay mixture 90 parts Calcium ligninsulfonate 5 parts or more are mixed and ground uniformly, mixed with an appropriate amount of water, kneaded, granulated, and dried to form granules.

Prescription example 5

Claims (10)

[Claims] (1) General formula (I) ▲Mathematical formulas, chemical formulas, tables, etc.▼(I) [In the formula, R^1 represents a lower alkyl group, R^2 represents a haloalkoxy group, and R^3 represents a halogen Indicates an atom, R
^4 is a cyanoalkyl group, a cyanoalkenyl group, a lower dialkoxyphosphinyl alkyl group, a 1,3-dioxolan-2-yl group, -C(R^5)_2-COR^6(
In the formula, R^5 may be the same or different and represents a hydrogen atom or a lower alkyl group, and R^6 represents a hydroxyl group, a lower alkoxy group, or a lower alkylthio group. ), -CH=N-
OR^7 (in the formula, R^7 is a hydrogen atom, a lower alkyl group,
Indicates a lower alkenyl group or a lower alkoxycarbonylalkyl group. ), -CH=CH-COR^8 (wherein, R
^8 represents a lower alkyl group, a lower alkoxy group, or a lower alkenyloxy group. ), -CH_2-A-R^9(
In the formula, R^9 represents a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower alkoxycarbonylalkyl group, or a lower acylalkylcarbonyl group, and A represents an oxygen atom or a sulfur atom. ) or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, R^1^0
represents a hydroxyl group or a lower alkoxy group, and R^1^1 represents a lower alkoxy group or a lower alkenyloxy group. )
, and X and Y may be the same or different and represent a halogen atom. ] A 3-substituted phenylpyrazole derivative or a salt thereof. (2) R^1 represents a lower alkyl group, R^2 represents a haloalkoxy group, R^3 represents a halogen atom, and R^
4 is -CH_2-A-R^9 (wherein R^9 represents a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower alkoxycarbonylalkyl group, or a lower acylalkylcarbonyl group, and A is oxygen The 3-substituted phenylpyrazole derivative or salt thereof according to claim 1, wherein X and Y may be the same or different and represent a halogen atom. (3) R^1 represents a lower alkyl group, R^2 represents a fluoroalkoxy group, R^3 represents a halogen atom,
R^4 represents -CH_2-A-R^9 (in the formula, R^9 represents a lower alkoxycarbonyl alkyl group, and A represents an oxygen atom), and X and Y may be the same or different, The 3-substituted phenylpyrazole derivative or salt thereof according to claim 2, which exhibits a halogen atom. (4) R^1 represents a methyl group, R^2 represents a difluoromethoxy group, R^3 represents a chlorine atom, and R^4 represents -
CH_2-A-R^9 (In the formula, R^9 represents a lower alkoxycarbonyl alkyl group, and A represents an oxygen atom.)
The 3-substituted phenylpyrazole derivative or salt thereof according to claim 3, wherein X represents a fluorine atom and Y represents a chlorine atom. (5) The 3-substituted phenylpyrazole derivative or salt thereof according to claim 3, which is the following compound. [1] 2-[2-chloro-5-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazole-3-
yl)-4-fluorobenzyloxy]ethyl acetate[2]2-[2-chloro-5-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazole-3-
yl)-4-fluorobenzyloxy]isopropyl acetate[3]2-[2-chloro-5-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazole-3-
ethyl)-4-fluorobenzyloxy]propionate (6) A herbicide containing the 3-substituted phenylpyrazole derivative or its salts according to claim 1 as an active ingredient. (7) A herbicide containing the 3-substituted phenylpyrazole derivative or its salts according to claim 2 as an active ingredient. (8) A herbicide containing the 3-substituted phenylpyrazole derivative or its salts according to claim 3 as an active ingredient. (9) A herbicide containing the 3-substituted phenylpyrazole derivative or its salts according to claim 4 as an active ingredient. (10) A herbicide containing the 3-substituted phenylpyrazole derivative or its salts according to claim 5 as an active ingredient.