JPH02212467A - Benzenesulfonic acid anilide and fungicide for agricultural purpose - Google Patents

Abstract

NEW MATERIAL:A compound of formula I [X is halogen; NO2, 1-3C (halo)alkyl, 1-3C haloalkoxy, 1-3C haloalkylthio, 1-3C haloalkylsulfonyl; n is 1 to 5; Y is O, S, SO2; Z is 1-3C haloalkyl; m is 1 to 3; W is halogen, NO2, 1-3C (halo)alkyl; p is 0 to 3 where the sum of m and p is 5 or less]. EXAMPLE:3-Trifluoromethylbenzenesulfonyl (4-trifluoromethoxy)anilide. USE:Fungicide for agricultural purposes. Especially it shows powerful action to control soil diseases. PREPARATION:For example, a compound of formula II (hal is halogen) is allowed to react with a compound of formula III (Ya is O, S) to give a compound of formula I where Y is O or S.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to novel benzenesulfonic acid anilides, their production method, and their use as agricultural fungicides.

US-3,034,955 (US patent), EP-O3 (European published patent) 193,3, known before the filing date of the present application
90 and JP-A-61-271270 describe that certain benzenesulfonic acid anilides are useful as insecticides or fungicides.

The present inventors have now discovered benzenesulfonic acid anilides represented by the following formula (1).

In the formula, X is a halogen atom, a nitro group, an alkyl group having 1 to 3 carbon atoms, a haloalkyl group having 1 to 3 carbon atoms, a haloalkoxy group having 1 to 3 carbon atoms, or a haloalkylthio group having 1 to 3 carbon atoms. or represents a haloalkylsulfonyl group having 1 to 3 carbon atoms, n represents 1.2, 3.4 or 5, Y represents an oxy group, thio group or sulfonyl group, and Z represents 1 to 3 carbon atoms represents a haloalkyl group, m is 1
．． 2 or 3, W represents a halogen atom, a nitro group, an alkyl group having 1 to 3 carbon atoms, or a haloalkyl group having 1 to 3 carbon atoms, and p represents OS 1, 2 or 3.

Here, the sum of m and P does not exceed 5.

The compound of formula (1) of the present invention can be synthesized, for example, by the following method.

Production method a): (Formula 3 when Y represents an oxy group or a thio group: In the formula, X and n are the same as above, hal represents a halogen atom, and a compound represented by the formula: In the formula, Z, m, W and p are the same as above, Ya represents an oxy group or a thio group, and is characterized by reacting with a compound represented by the following formula: In the formula, X, n, Ya, Z, m, W and p is the same as above, A method for producing a benzenesulfonic acid anilide represented by:

Production method b): [When Y represents a sulfonyl group: Formula 3: In the formula, X, n, Z, m, W and p are the same as above, characterized by reacting a compound represented by the following with an oxidizing agent A method for producing a benzenesulfonic acid anilide represented by the formula: where X, n, Z, m, W and p are the same as above.

The compound of formula (I) of the present invention exhibits bactericidal activity, particularly as a potent soil disease control agent.

According to the present invention, the benzenesulfonic acid anilide of formula (1) surprisingly exhibits superior bactericidal activity compared to the compounds described in the above-mentioned known publications that are similar to the compounds of the present invention. , and the clubroot disease of Brassicaceae plants (Plaamodiophora), which is an important target for control.
It exhibits extremely excellent bactericidal activity against Brassicae.

In the compound of formula (1) of the present invention, X is preferably a fluorine atom, a chlorine atom, a nitro group, a methyl group, a haloalkyl group having 1 to 2 carbon atoms, a haloalkoxy group having 1 to 2 carbon atoms, or a haloalkoxy group having 1 to 2 carbon atoms. represents a haloalkylthio group having 1 to 2 carbon atoms or a haloalkylsulfonyl group having 1 to 2 carbon atoms, n represents 1.2 or 3, Y represents an oxy group, thio group, or sulfonyl group, and 2 represents the number of carbon atoms represents 1 to 2 haloalkyl groups, m is 1
, or 2, W represents a fluorine atom, a chlorine atom, a nitro group, a methyl group, or a haloalkyl group having 1 to 2 carbon atoms, and P represents 0.1 or 2.

Furthermore, in formula (1), particularly preferably, X represents a chlorine atom, a nitro group, a methyl group, or a trifluoromethyl group, n represents 1 or 2, and Y represents an oxy group, a thio group, or represents a sulfonyl group, Z is a trifluoromethyl group, 2.2.2-)lifluoroethyl group, 1.1.2.2-tetrafluoroethyl group or 2-chloro-1,1,2-)lifluoro represents an ethyl group, m represents 1, W represents a chlorine atom, and p represents 0, 1 or 2.

And, as specific examples of the compound of formula (I) of the present invention,
In particular, the following compounds may be mentioned.

3-trifluoromethylbenzenesulfonic acid (4-trifluoromethoxy)anilide, 4-chloro-3-trifluoromethylbenzenesulfonic acid (4-trifluoromethoxy)anilide, 3.5-bis(trifluoromethyl)benzenesulfone Acid (4-trifluoromethoxy)anilide, 2-methyl-5-nitrobenzenesulfonic acid (4-trifluoromethoxy)anilide, 4-chloro-3-trifluoromethylbenzenesulfonic acid (4-trifluoromethylthio)anilide , 4-trifluoromethylbenzenesulfonic acid (4-trifluoromethylthio)anilide, 3,5-bis(trifluoromethyl)benzenesulfonic acid (4-trifluoromethylthio)anilide.

In production method a], for example, when 4-trifluoromethylaniline and 4-chloro-3-trifluoromethylbenzenesulfonyl chloride are used as raw materials, the reaction formula is shown below.

When Nilin is used, the reaction formula is shown below.

In the F s production method b), for example, when 4-chloro-3-trifluoromethylbenzenesulfonic acid 4-(trifluoromethylthio)anilide and hydrogen peroxide are used as raw materials, the reaction is expressed by the following reaction formula.

In the above production method a), the compound of formula (II) which is a raw material is defined based on the above definitions of X, n and hal, and preferably, X and n have the same meanings as the above preferred definitions. , hal represents a chlorine atom or a fluorine atom.

The compound of formula (II) is well known in the field of organic chemistry, and specific examples thereof include the following.

3-trifluoromethylbenzenesulfonyl chloride, 4-chloro-3-trifluoromethylbenzenesulfonyl chloride, 2.4-dichloro-5-trifluoromethylbenzenesulfonyl chloride, 4-trifluoromethylbenzenesulfonyl chloride, 2-chloro- 4-Trifluoromethylbenzenesulfonyl chloride, 3.5-bis(trifluoromethyl)benzenesulfonyl chloride, 3.4-bis(trifluoromethyl)benzenesulfonyl chloride, 2-methyl-5-nitrobenzenesulfonyl chloride , 4-trifluoromethoxybenzenesulfonyl chloride, 4-trifluoromethylthiobenzenesulfonyl chloride, 4-(2,2,2-)lifluoroethylthio)benzenesulfonyl chloride.

In the above production method a), the compound of formula (Ill) which is a raw material means one based on the definitions of Z, m, W, p and Ya above.

In formula (I), Z, m, W and p preferably have the same meanings as the above preferred definitions, and Ya preferably represents an oxy group or a thio group.

The compound of formula (I[[) is also well known in the field of organic chemistry, and specific examples thereof include the following.

3-trifluoromethoxyaniline, 4-trifluoromethoxyaniline, 2-chloro-4-trifluoromethoxyaniline, 4-
Trifluoromethylaniline, 2-chloro-4-trifluoromethylthioaniline 4-
(1,1,2,2-tetrafluoroethoxy)aniline, 4-(1,1,2,2-tetrafluoroethylthio)
Aniline, 3.4-bis(trifluoromethoxy)aniline, 4-
Difluoromethoxy-3-trifluoromethylaniline, 4-chloro-3-trifluoromethylthioaniline.

In production method b), the compound (Ia') which is a raw material means one based on the definitions of X, n, Z, m, W and p, preferably having the same meaning as the preferred definitions above. show.

The compound of formula (Ia') can be produced by the above production method a), and specific examples thereof include the following.

4-trifluoromethylbenzenesulfonic acid 4-(trifluoromethylthio)anilide, 3-trifluoromethylbenzenesulfonic acid 4-(trifluoromethylthio)
anilide, 4-chloro-3-trifluoromethylbenzenesulfonic acid 4-(trifluoromethylthio)anilide, 3.5-bis(trifluoromethyl)benzenesulfonic acid 4-(trifluoromethylthio)anilide, 2-methyl-5 -Nitrobenzenesulfonic acid 4-(trifluoromethylthio)anilide.

In the above production method b), examples of the oxidizing agent include organic peroxides such as meta-chloroperbenzoic acid or hydrogen peroxide.

When carrying out the above manufacturing method a), as a suitable diluent,
All inert organic solvents may be mentioned.

Examples of such diluents include aliphatic, cycloaliphatic and aromatic hydrocarbons (optionally chlorinated)
For example, hexane, cyclohexane, petroleum ether, ligroin, benzene, toluene, xylene, methylene chloride, chloroform, carbon tetrachloride, ethylene chloride, chlorhensen; other ethers, such as diethyl ether, methyl ethyl ether, Z! SO-
Propyl ether, dibutyl ether, dioxane, tetrahydrofuran; nitriles such as acetonitrile, propionitrile and bases such as pyridine can be mentioned.

Preparation method a) is preferably carried out in the presence of an acid binder, such as carbonates and bicarbonates of alkali metals, tertiary amines Hfj4, etc. Triethylamine, tributylamine, 1. l, 4,4-tetramethylethylenediamine, N
, N-dimethylaniline, N,N-diethylaniline,
Pyridine, 4-dimethylaminopyrimidine, 1,4-diazabicyclo(2,2,2)octane (DABCO)
, 1,8-diazabicyclo(5,4,0)undec-7
-en etc. can be mentioned.

Process a) can be carried out within a substantially wide temperature range. Generally, it can be carried out at a temperature between about 30 and about 300°C, preferably between about 50 and about 250°C. Further, although it is desirable that the various reactions be carried out under normal pressure, they can also be operated under increased pressure or reduced pressure.

In carrying out production method a), for example, the compound of formula (II) is added in an amount of 1 mole to 1.3 times mole per 1 mole of the compound of formula (I) in an inert solvent such as pyridine. Depending on the reaction, the target compound can be obtained by reacting in the presence of 4-dimethylaminopyridine in an amount of 0.3 molar to 1.5 times the molar amount.

When carrying out the above manufacturing method b), as a suitable diluent,
Mention may be made of all inert organic solvents.

Examples of such diluents include, when the oxidizing agent is an organic peroxide, aliphatic, cycloaliphatic and aromatic hydrocarbons (optionally chlorinated) such as hexane,
Examples include cyclohexane, benzene, toluene, xylene, methylene chloride, chloroform, carbon tetrachloride, ethylene chloride, chlorobenzene; and others.

When the oxidizing agent is hydrogen peroxide in carrying out the above production method b), examples of the diluent include water (which may be basic, neutral or acidic); carboxylic acids such as acetic acid.

Process b) can be carried out within a substantially wide temperature range. When using an organic peroxide as the oxidizing agent, it can generally be carried out at temperatures between about 0 and about 150<0>C, preferably between about 25 and about 100<0>C. When the oxidizing agent is hydrogen peroxide, the oxidizing agent is generally about 15° to about 120°
C1 can preferably be carried out between about 25 and about 100°C. Further, although the reaction is preferably carried out under normal pressure, it can also be operated under increased pressure or reduced pressure.

When carrying out production method b), for example, formula (I b)
The target compound can be obtained by reacting 2 to 3 times the mole of the oxidizing agent with respect to 1 mole of the compound, for example, in glacial acetic acid.

The active compounds according to the invention exhibit a strong fungicidal action and can be used in practice for controlling unwanted plant pathogens.

The active compounds of the invention are generally used as M (mold)icides for Plasmodioholomycetes (Plaa-modi).
ophorosycetes), omycetes (Oos
ycetes), Chytridiomycetes (Chytri
diosycates), Zygo■y
cetes), Ascosycetes
s), Basidiowy-ce
Les) and Deuteromycetes
It can be used against various plant diseases caused by Pseudomonadaceae (P. etes) and as a fungicide (bacteria).
seudoaonadaceae), Rhizobium family (R
hlzobi-aceae), Enterobacteriaceae (
Enterobacte-riacsae), Corynebacterium family (Corynebacterium)
e) and Streptomycetes (Strepto-myc
It can be used against various plant diseases caused by (Etaceae).

For example, the compound of the present invention is particularly suitable for clubroot disease (Pl) belonging to Plasmodeioholomycetes.
Asmodlophora brassicae).

The active compound of the present invention exhibits good compatibility with plants at the concentration of active compound necessary for controlling plant pathogens, and therefore, when used, it is necessary to treat the above-ground parts of the plant with a drug, It enables chemical treatment of rootstocks and seeds, as well as soil treatment.

Furthermore, the compounds of the present invention have low toxicity even to warm-blooded animals and can be used safely.

The active compounds according to the invention can be put into customary pharmaceutical forms. And such forms include solutions, emulsions, powders, foams, pastes, granules, aerosols, active compound infiltration - natural and synthetic, microcapsules, coatings for seeds, preparations with combustion devices. (e.g. combustion devices include fumigation and fume cartridges, cans and coils), +L, 7ULV (r-le) mist (col)
d +wist), warm mist (mar-mist)
)).

These formulations can be manufactured by known methods.

Such methods include, for example, combining the active compound with a vehicle, i.e. a liquid diluent; a liquefied gas diluent; a solid diluent or carrier; optionally a surfactant, i.e. an emulsifier and/or a dispersant and/or a foam. This is done by using a forming agent and mixing.

When using water as a developing agent, for example, organic solvents can also be used as co-solvents.

Liquid diluents or carriers generally include aromatic hydrocarbons (e.g. xylene, toluene, alkylnaphthalenes, etc.), chlorinated aromatic or chlorinated aliphatic hydrocarbons (
(e.g., chlorobenzenes, ethylene chlorides, methylene chloride, etc.), aliphatic hydrocarbons (e.g., cyclohexane, etc., paraffin II (e.g., mineral oil fraction, etc.)), alcohols (e.g., butanol, glycols, and their ethers and esters). ), ketones IIC such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone), strongly polar solvents (such as dimethylformamide, dimethyl sulfoxide, etc.) and water.

The liquefied gas diluent or carrier is a gas at normal temperature and pressure, and examples thereof include butane, propane, nitrogen gas,
Mention may be made of aerosol propellants such as carbon dioxide and halogenated hydrocarbons.

Solid diluents include soil natural minerals (e.g. kaolin, clay, talc, chalk, quartz, attapulgite,
montmorillonite or diatomaceous earth), soil synthetic minerals (for example, highly dispersed silicic acid, alumina, silicates, etc.).

Solid carriers for granules include crushed and fractionated rocks (e.g. calcite, marble, pumice, sepiolite, dolomite, etc.), synthetic piles of inorganic and organic materials, and organic materials (e.g. sawdust, Examples include fine grains of coconut (cobs of coconut, cobs of corn, stalks of tobacco, etc.).

Emulsifiers and/or foaming agents include nonionic and anionic emulsifiers [e.g., polyoxyethylene fatty acid esters, polyoxyethylene fatty acid alcohol ethers (e.g., alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfones); salts, etc.)] and albumin hydrolysis products.

Examples of dispersants include lignin sulfide waste liquid,
and includes methylcellulose.

Fixing agents can also be used in the formulations (powders, granules, emulsions), such fixing agents include carboxymethylcellulose and natural and synthetic polymers such as gum arabic, polyvinyl alcohol and polyvinyl acetate. Can be done.

Coloring agents may also be used, including inorganic pigments such as iron oxide, titanium oxide and Prussian blue, and organic dyes such as alizarin dyes, azo dyes or metal phthalocyanine dyes, and also iron, Mention may be made of such trace elements as manganese, boron, carbo, cobalt, molybdenum, their salts of zinc.

The formulations may generally contain from 0.1 to 95% by weight, preferably from 0.5 to 90% by weight of said active ingredient.

The active compounds of the invention may be used in the above-mentioned formulations or in various use forms in combination with other known active compounds, such as fungicides, bactericides, insecticides, acaricides, nematocides, herbicides, bird repellents. , a growth regulator, a fertilizer and/or a soil conditioner may also be present.

When using the active compounds of the invention, they can be used directly as such, or in the form of formulations such as spray preparations, emulsions, suspensions, powders, pastes and granules, or prepared in further dilutions. It can be used in the following manner. The active compound can then be applied in the usual manner, e.g. by liquid spraying (
waterjng), dipping, spraying,
atos1siyig+ sitting), fumigation (
vaporing), irrigation, suspension formation, application, dusting,
It can be used in dusting, powder coating, wet coating, wet coating, gluing or feather coating.

When treating the various parts of the plant, the concentration of active compound in the actual use form can be varied within a substantial range. The amount is generally 0.0001 to 1% by weight, preferably 0.001 to 0.5% by weight.

For seed treatment, the active compound should be added to o per cg of seed.
, ooi to 50 g, preferably 0.01 to 10 g can generally be used.

When treating soil, 0.00001~
A concentration of active compound of 0.1% by weight, especially from 0.0001 to 0.02% by weight can be used per vessel.

Next, the content of the present invention will be specifically explained with reference to Examples, but the present invention should not be limited to these examples.

Production Examples Example 1 4-Chloro-3-trifluoromethylbenzenesulfonyl chloride (2,79 g) was added to a solution of 4-trifluoromethylthioaniline (2,32 g) in pyridine (40 wj).
and heated under reflux for 3 hours.

After the reaction, the solvent is distilled off under reduced pressure. Add 5% hydrochloric acid (2
0id) and extracted with dichloromethane (20id x 2). The organic layer is washed with water, dried over anhydrous magnesium sulfate, and then the solvent is distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 4-chloro-3-trifluoromethylbenzenesulfonic acid 4-(trifluoromethylthio)anilide (&56 g). mp, 8B-
90°C0 Example 2 4-chloro-3-trifluoromethylbenzenesulfonic acid 4-()lifluoromethanesulfonyl)anilide (1
, 39g). 147-150"C.

A compound that can be synthesized by the same manufacturing method as in Examples 1 and 2 was added to the following No. 1 compound together with the compounds of Examples 1 and 2.
Shown in the table.

(Left below) 4-chloro-3-trifluoromethylbenzenesulfonic acid 4-(trifluoromethylthio)anilide (1,31
g> in glacial acetic acid (30 m).

Add 34% hydrogen peroxide solution (1 m) to this solution, and
After the reaction was stirred at 80° C. for 5 hours, the mixture was concentrated under reduced pressure, a small amount of water was added to the residue, and the mixture was neutralized with potassium carbonate. After extraction with dichloromethane (30dx2) and drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. When the residue is purified by recrystallization, Table 1 (Continued) Table 1 (Continued) Table 1 (Continued) Table 1 (Continued) Table 1 (Continued) Table 1 (Continued) Table 1 (continued) Table 1 (continued) Table 4 (continued) Table 1 (continued) Table 1 (continued) Table 1 (continued) Table 1 (continued) Table 1 (continued) Table 1 (continued) ) Table 1 (Continued) Table 1 (Continued) Table 1 (Continued) Table 1 (Continued) Table 4 (Continued) Table 1 (Continued) Table 1 (Continued) Table 1 (Continued) Table 1 (continued) Table 1 (continued) Table 1 (continued) Table 1 (continued) Table 1 (continued) Table 1 (continued) Table 4 (continued) Table 1 (continued) Table 1 (continued) Table 1 (continued) Table 1 (continued) Table 1 (continued) Table 1 (continued) Table 1 (continued) Table 1 (!jli) Table 1 (continued) Table 1 ( (continued) Table 1 (continued) Part 1S (continued) Table 1 (continued) Table 4 (continued) Table 4 (continued) Table 1 (continued) Table 1 (continued) Disease Table 1 (continued) Part Table 1 (continued) Table 1 (continued) Table 1 (continued) Table 4 (continued) Table 1 (continued) Table 1 (continued) Table 1 (continued) Table 1 (1 sale) Part 1 Table (Continued) Table 1 (Continued) Table 4 (Continued) Table 1 (Continued) Table 1 (Continued) Table 1 (M) Table 4 (Continued) Table 1 (Continued) Table 1 (continued) Table 1 (continued) Table 4 (continued) Table 1 (continued) Table 1 (M) Table 1 (IN) Table 1 (continued) Table 1 (continued) Table 1 (continued) ) Table 1 (continued) Table 1 (continued) Table 1 (continued) Table 1 (continued) Table 1 (continued) Table 1 (continued) Table 1 (continued) Table 1 (M, ) Table 1 (1 sale) Table 1 (continued) Table 1 (continued) Table 4 (continued) Table 1 (continued) Table 1 (Continued) Table 1 (Continued) Table 1 (Continued) Table 4 (Continued) Table 1 (Continued) Table 1 (Continued) Table 4 (Continued) Table 1 (Continued) Table 1 (Continued) Table 1 (Continued) Table 1 (Continued) Table 1 (continued) Table 1 (continued) Chapter 18 (continued) Table 1 (wc) Table 1 (continued) Table 1 (continued) Table 1 (continued) Table 1 (continued) Table 1 (continued) Table 1 (!*) Table 1 (continued) Table 1 (continued) Table 1 (continued) Table 1 (continued) Table 1 (continued) Biological test comparison compound CF.

C.F.

(JP 61-271270) Example 3 Komatsuna root club disease control test Preparation of active compound Active compound 1.5 parts Powdered clay 98 The above materials were ground and mixed to form a powder.

Part Table 1 (!Sold) Test method Place the clubroot fungus (Plaasodi) in a clay pot with a diameter of 21C1.
-ophora brassicae) contaminated soil was packed, and the powder of the compound of the present invention prepared as described above was uniformly mixed therein to a predetermined concentration.

In this soil, 20 seeds of Komatsuna (variety: Misugi) were sown per pot. After growing in an air-conditioned greenhouse at 20°C for 4 weeks, the Komatsuna plants were dug up and the disease state was evaluated according to the following criteria, and the control efficacy was calculated. In addition, no drug damage was observed in the test.

Disease severity 3: L + Number of plants with significantly enlarged roots due to root galls 2: Lx Number of plants with root galls observed but limited to the taproot 1: L, number of plants with slight root galls 0: L4
Number of healthy stocks (%) 3x (L++L, t+Ls+La)
The results are shown in Table 2.

(Margin below) No. table

Claims (5)

[Claims] (1) Formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ In the formula, X is a halogen atom, a nitro group, an alkyl group having 1 to 3 carbon atoms, a haloalkyl group having 1 to 3 carbon atoms, represents a haloalkoxy group, a haloalkylthio group having 1 to 3 carbon atoms, or a haloalkylsulfonyl group having 1 to 3 carbon atoms, n represents 1, 2, 3, 4, or 5, and Y represents an oxy group, a thio group, or represents a sulfonyl group, Z represents a haloalkyl group having 1 to 3 carbon atoms, and m represents 1
, 2 or 3, W represents a halogen atom, a nitro group, an alkyl group having 1 to 3 carbon atoms, or a haloalkyl group having 1 to 3 carbon atoms, and p represents 0, 1, 2 or 3. , [where the sum of m and p does not exceed 5]. (2) X is a fluorine atom, a chlorine atom, a nitro group, a methyl group, a haloalkyl group having 1 to 2 carbon atoms, a haloalkoxy group having 1 to 2 carbon atoms, a haloalkylthio group having 1 to 2 carbon atoms, or a haloalkylthio group having 1 to 2 carbon atoms 2 represents a haloalkylsulfonyl group, n represents 1, 2, or 3, Y represents an oxy group, thio group, or sulfonyl group, Z represents a haloalkyl group having 1 to 2 carbon atoms, and m represents 1
, or 2, W represents a fluorine atom, a chlorine atom, a nitro group, a methyl group, or a haloalkyl group having 1 to 2 carbon atoms, and p represents 0, 1, or 2, according to claim (1). compound. (3) X represents a chlorine atom, a nitro group, a methyl group, or a trifluoromethyl group, n represents 1 or 2, Y represents an oxy group, a thio group, or a sulfonyl group, and Z represents a trifluoromethyl group, 2 , 2,2-trifluoroethyl group, 1,1,2,2-tetrafluoroethyl group, or 2-chloro-1,1,2-trifluoroethyl group, m represents 1, and W represents a chlorine atom. The compound according to claim 1, wherein p represents 0, 1 or 2. (4) Formula ▲ Numerical formula, chemical formula, table, etc. are available ▼ In the formula, X is a halogen atom, a nitro group, an alkyl group having 1 to 3 carbon atoms, a haloalkyl group having 1 to 3 carbon atoms, represents a haloalkoxy group, a haloalkylthio group having 1 to 3 carbon atoms, or a haloalkylsulfonyl group having 1 to 3 carbon atoms, n represents 1, 2, 3, 4, or 5, and Y represents an oxy group, a thio group, or represents a sulfonyl group, Z represents a haloalkyl group having 1 to 3 carbon atoms, and m represents 1
, 2 or 3, W represents a halogen atom, a nitro group, an alkyl group having 1 to 3 carbon atoms, or a haloalkyl group having 1 to 3 carbon atoms, and p represents 0, 1, 2 or 3. , [wherein the sum of m and p does not exceed 5] An agricultural fungicide containing a benzenesulfonic acid anilide as an active ingredient. (5) The agricultural fungicide according to claim (4), which is used for controlling soil diseases.