JPH09268169A - Salicylic acid anilide derivative and controlling agent for plant disease injury containing the same derivative as active ingredient - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a new compound useful as a controlling agent for plant disease injury and excellent in germicidal activity and safety to crops. SOLUTION: This compound is represented by formula I [R is H, a 1-6C alkanoyl, etc.; W is H, a halogen, etc. ; X is nitro, cyano or trifluoromethyl; Y and Z are each H, a halogen, etc.; A and B are each O or S; (p) and (q) are each O or 1 and (m) is 0-4 and (n) is 0-6, except when X is nitro and (p) and (n) are both 0], e.g. 2-hydroxy-5 nitro-4' (4-phenylbutoxy)benzanilide. The compound of formula I is obtained by reacting salicylic acids of formula II with anilines of formula III in the presence of a condensing agent (e.g. phosphorus trichloride) in a solvent (e.g. toluene) at -10 deg.C to a boiling point of the solvent. The compound is useful for controlling various kinds of disease injuries which become problem on agriculture and horticulture, especially late blight of tomato and potato and downy mildew of grape, cucumber, onion, etc., caused by Mastigomycotina such as Pythiaceae and Peronosporacease.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a salicylic acid anilide derivative and a plant disease controlling agent containing the same as an active ingredient.

[0002]

2. Description of the Related Art Up to now, it has been known that certain anilide salicylates have bactericidal activity. For example, US Pat. No. 3,823,236 and US Pat. No. 3,9.
14,418, U.S. Pat. No. 2,802,029 and WO92217066 disclose that certain 5-substituted anilide salicylates can be used as agricultural plant disease control agents.

[0003]

However, the safety of anilide salicylates described in the above specification against plants or the efficacy as a plant disease controlling agent is
It is not always satisfactory in practical use. It is an object of the present invention to provide a novel anilide salicylate derivative excellent in bactericidal activity and safety against crops and its use.

[0004]

The present invention is based on the general formula (1)
And a plant disease control agent containing the salicylic acid anilide derivative represented by:

[0005]

Embedded image [In the formula, R represents a hydrogen atom, a C _{1 to} C ₆ alkanoyl group, an alkali metal cation or an alkaline earth metal cation equivalent, or an ammonium cation which may be optionally mono- or polysubstituted with the same or different substituents. Represents a hydrogen atom, a halogen atom, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkoxy group, a formamide group, X represents a nitro group, a cyano group, a trifluoromethyl group, Y and Z is a hydrogen atom, a halogen atom, C _{1 to} C ₆
Represents an alkyl group, a C ₁ -C ₆ haloalkyl group, a phenyl group, an anilino group, a benzoyl group, A and B represent an oxygen atom and a sulfur atom, p and q represent an integer of 0 or 1, and m is 0 to Represents an integer of 4, and n represents an integer of 0 to 6. However, the case where X is a nitro group and both p and n are 0 is excluded. ]

[0006]

BEST MODE FOR CARRYING OUT THE INVENTION In the general formula (1), C _{1 to} C ₆
Examples of the alkanoyl group include an acetyl group, a propionyl group, a pivaloyl group and a benzylcarbonyl group. The C ₁ -C ₆ alkyl group include a methyl group, an ethyl group, n- propyl group, iso- propyl, tert- butyl group, sec- butyl group, a pentyl group, a hexyl group or the like. Examples of the C ₁ -C ₆ alkoxy group include a methoxy group, an ethoxy group, an n-propoxy group, an iso-propoxy group, a butoxy group and a hexyloxy group. Examples of the halogen atom include fluorine, chlorine, bromine, iodine and the like.

The compounds of the present invention are useful against various diseases which pose problems in agriculture and horticulture, such as vegetables, fruit trees, paddy rice and horticultural plants. Especially, the plague (Pythiac
eae), and plant diseases caused by typical plant pathogens of flagellar fungi such as downy mildew (Peronosporacease). Such plant diseases include tomato late blight, potato late blight, grape downy mildew, cucumber downy mildew, onion downy mildew and the like. Next, the method for producing the compound of the present invention will be described in detail. The compound of the present invention can be produced, for example, by the following reaction formula.

[0008]

Embedded image

In the above equation, W, X, Y, Z, A, B, m,
n, o, p and q have the same meanings as described above, and Halo
Represents a halogen atom. The compound represented by the general formula (4) is the compound of the present invention. More specifically, in this production method, the salicylic acid represented by the formula (2) and the aniline represented by the general formula (3) in step 1 are reacted in the presence of a suitable condensing agent in an inert solvent. This shows that the salicylic acid anilides represented by the general formula (4) can be produced. In addition, the salicylic acid anilides represented by the general formula (4) are obtained by converting the acid halide of the salicylic acid represented by the general formula (5) and the aniline represented by the general formula (3) into a suitable acid binder. It can also be produced by reacting in the presence. Examples of the condensing agent used in step 1 include phosphorus halides such as phosphorus trichloride, phosphorus tribromide, phosphorus pentachloride, phosphorus oxychloride, and thionyl chloride; mixed acid anhydrides such as ethyl chloroformate and methanesulfonyl chloride. Product generator,
Carbodiimides such as N, N'-dicyclohexylcarbodiimide (DCC) or other condensing agents such as N, N-carbonyldiimidazole, 2-ethoxy-N
-Ethoxycarbonyl-1,2-dihydroquinoline (E
EDQ), triphenylphosphine-carbon tetrachloride (complex) and the like.

As the solvent, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, hexane,
Aliphatic hydrocarbons such as cyclohexane and petroleum ether,
Aliphatic halogenated hydrocarbons such as dichloromethane, 1,2-chloroethane, chloroform and carbon tetrachloride, diethyl ether, diisopropyl ether, dioxane,
Ethers such as tetrahydrofuran, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, ketones such as acetone, 2-butanone, methyl isobutyl ketone, acetonitrile, propionitrile,
Nitriles such as benzonitrile, N, N-dimethylformamide, hexamethylphosphoric triamide (HM
Examples thereof include amides such as PA), sulfoxides such as dimethyl sulfoxide, and mixed solvents thereof.

The amount of the reagent to be used in the reaction is not particularly limited, but usually 1 mol of the salicylic acid represented by the formula (2) and 1. 1 mol of the aniline represented by the general formula (3). 0
~ 2.0 mol, preferably 1.0 to 1.3 mol, it is preferable to use the condensing agent 1.0 to 5.0 mol,
It is preferably used in the range of 1.0 to 2.5 mol. Although the reaction temperature is not particularly limited, it is usually within the range of -10 ° C to the boiling temperature of the solvent used or lower. The reaction time varies depending on the above concentration, temperature, etc., but is usually 5
It can be produced by reacting for 10 hours. The salicylic acid represented by the formula (2) is industrially easily available. Further, the anilines represented by the general formula (3) are industrially easily available or can be produced according to a known method.

The solvent used in step 2 is similar to that described in step 1. Examples of the acid binder include alkali metal hydroxides or alkaline earth metal hydroxides such as sodium hydroxide, potassium hydroxide and calcium hydroxide, ammonium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate and hydrogen carbonate. Alkali metal carbonates such as potassium, ammonium carbonate, or alkali metal or alkaline earth metal acetates such as sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium hydride, potassium hydride, calcium hydride, etc. Alkali metal or alkaline earth metal hydrides, or trimethylamine, triethylamine,
N, N-dimethylaniline, pyridine, 4- (dimethylamino) pyridine, diazabicyclooctane (DABC
O), diazabicyclononene (DBN), diazabicycloundecene (DBU), and other tertiary amines.

The amount of the reagent used in the reaction is not particularly limited, but it is usually an aniline represented by the general formula (3) per 1 mol of the acid halide of salicylic acid represented by the formula (5). 1.0-2.0 mol, preferably 1.0-1.
It is preferably used in the range of 3 mol, and the acid binder is used in the range of 1.0 to 5.0 mol, preferably 1.0 to 2.5 mol. The reaction temperature is not particularly limited,
Usually, it is in the range of -10 ° C to the boiling point temperature of the solvent to be used. The reaction time varies depending on the above-mentioned concentration, temperature and the like, but it can be usually produced by reacting for 1 to 5 hours. Further, the compound of the present invention represented by the general formula (6) can be produced from the salicylic acid anilide represented by the above general formula (4) according to the following reaction formula.

[0014]

Embedded image

In the above equation, W, X, Y, Z, A, B, m,
n, p and q have the same meanings as described above, and R is C ₁ -C ₆
Represents an alkanoyl group. The compounds represented by the general formulas (4) and (6) are the compounds of the present invention. More specifically, this production method is carried out by reacting salicylic acid anilides represented by the formula (4) with an acylating agent in step 3 in the presence of a suitable acid binder in a solvent-free or inert solvent. It is shown that salicylic acid anilides represented by the formula (6) can be produced.

The solvent and acid binder used in step 3 are the same as those described in step 2. Examples of the acylating agent include acid anhydrides such as acetic anhydride and propionic anhydride, and acid halides such as acetyl chloride, acetyl bromide, propionyl chloride, pivaloyl chloride and phenylacetic acid chloride.

The amount of the reagent to be used in the reaction is not particularly limited, but usually 1.0 to 2.0 mol of the acylating agent relative to 1 mol of salicylic acid anilide represented by the formula (4), It is preferably used in the range of 1.0 to 1.3 mol,
The acid binder is 1.0 to 5.0 mol, preferably 1.
It is preferably used in the range of 0 to 2.5 mol. Although the reaction temperature is not particularly limited, it is usually within the range of -10 ° C to the boiling point temperature of the solvent used. The reaction time varies depending on the above-mentioned concentration, temperature and the like, but it can be usually produced by reacting for 1 to 5 hours. Further, the compound of the present invention represented by the general formula (6) can be produced from the salicylic acid anilide represented by the above general formula (4) according to the following reaction formula.

[0018]

Embedded image

In the above equation, W, X, Y, Z, A, B, m,
n, p and q have the same meanings as described above, and R represents an alkali metal cation or an alkaline earth metal cation equivalent or an ammonium cation equivalent optionally mono- or polysubstituted with the same or different substituents. Represent The compounds represented by the general formulas (4) and (6) are the compounds of the present invention. More specifically, this production method is carried out by reacting the salicylic acid anilides represented by the formula (4) with an acid binder in Step 4 in the absence of solvent or an inert solvent to obtain the salicylic acid represented by the general formula (6). It shows that anilides can be produced.

The solvent and the acid binder used in step 4 are the same as those described in step 2. Examples of the acid binder include alkali metal hydroxides or alkaline earth metal hydroxides such as sodium hydroxide, potassium hydroxide and calcium hydroxide, and alkali metal hydroxides such as sodium carbonate, potassium carbonate, sodium hydrogen carbonate and potassium hydrogen carbonate. Carbonate, or an alkali metal or alkaline earth metal acetate such as sodium acetate, potassium acetate or calcium acetate, an alkali metal or alkaline earth metal hydride such as sodium hydride, potassium hydride or calcium hydride, Alkali metals or alkaline earth metals such as sodium, potassium and calcium, alcoholates such as sodium methylate and potassium t-butoxide, trimethylamine, diisopropylamine, triethylamine, ethanolamine, triethanolamine, etc. Amines, and the like.

The amount of the reagent used for the reaction is not particularly limited, but usually 1.0 to 2.0 mol of the acid binder per 1 mol of salicylic acid anilide represented by the formula (4), It is preferable to use it in a range of 1.0 to 1.3 mol. Although the reaction temperature is not particularly limited, it is usually within the range of -10 ° C to the boiling temperature of the solvent used or lower. The reaction time is
Although it varies depending on the above-mentioned concentration, temperature, etc., it can be usually produced by reacting for 1 to 5 hours. The object compound of the present invention can be purified by usual means such as concentration, filtration and recrystallization.

When the compound of the present invention is used as an active ingredient of a bactericide, it may be used as it is without adding any other ingredient, but it is usually used as a solid carrier, liquid carrier, gaseous carrier, bait, etc. The mixture is mixed, and if necessary, a surfactant and other auxiliary agents for formulation are added, and the mixture is formulated into an oil, an emulsion, a wettable powder, a granule, a powder, an aerosol, an aerosol, and the like for use. In these preparations, it is usually preferable that the compound of the present invention is contained as an active ingredient in an amount of 0.01 to 95% by weight.

Examples of solid carriers used for formulation include clays (kaolin clay, diatomaceous earth, synthetic hydrous silicon oxide, bentonite, fubasami clay, acid clay, etc.), talcs, ceramics, and other inorganic minerals (celite, Quartz, sulfur, activated carbon, calcium carbonate, hydrated silica, etc.), chemical fertilizers (ammonium sulfate, phosphorus ammonium, ammonium nitrate, urea, ammonium salt, etc.)
Examples of the liquid carrier include water, alcohols (methanol, ethanol, etc.), ketones (acetone, methyl ethyl ketone, etc.), aromatic hydrocarbons (benzene, toluene, xylene, etc.). Ethylbenzene, methylnaphthalene, etc.), aliphatic hydrocarbons (hexane, cyclohexane, kerosene, light oil, etc.), esters (ethyl acetate, butyl acetate, etc.), nitriles (acetonitrile, isobutyronitrile, etc.), ethers (diisopropyl) Ether, dioxane, etc.),
Acid amides (N, N-dimethylformamide, N, N-dimethylacetamide, etc.), halogenated hydrocarbons (dichloromethane, trichloroethane, carbon tetrachloride, etc.), dimethyl sulfoxide, soybean oil, vegetable oils such as cottonseed oil, and the like can be mentioned. Examples of the gaseous carrier, that is, the propellant include butane gas, LPG (liquefied petroleum gas), dimethyl ether, carbon dioxide gas and the like.

Examples of the surfactant include alkyl sulfates, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers and their polyoxyethylenated products, polyethylene glycol ethers, polyhydric alcohol esters, sugar alcohols. Examples include derivatives.

Examples of auxiliary agents for formulation such as a sticking agent and a dispersant are casein, gelatin, polysaccharides (starch powder,
Gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, sugars, synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.), and examples of stabilizers include PAP (acidic phosphoric acid). Isopropyl), BHT (2,
6-di-tert-butyl-4-methylphenol), BH
A (2-tert-butyl-4-methoxyphenol and 3-
(tert-butyl-4-methoxyphenol mixture), vegetable oil, mineral oil, surfactant, fatty acid, or ester thereof and the like. The preparation thus obtained is used as it is or diluted with water or the like. It can also be used simultaneously with or without mixing with other fungicides, nematicides, acaricides, herbicides, plant growth regulators and synergists.

When the compound of the present invention is used as an agricultural fungicide, the application rate is usually 0.1 to 100 g of the active ingredient per 10 ares, and the emulsion, wettable powder, flowable agent and the like are treated with water. When used by diluting with, the application concentration is usually 0.1 ppm to 1000 ppm, and it is preferable to apply the granules, powders and the like as they are without any dilution. These application rates and application concentrations differ depending on the type of preparation, application time, application place, application method, type of pest, degree of damage, etc., and may be increased or decreased without being affected by the above range. can do.

[0027]

EXAMPLES The present invention will be described in more detail below with reference to production examples, formulation examples and test examples, but the present invention is not limited thereto. First, Production Examples of the compound of the present invention will be shown.

Production Example 1 2-Hydroxy-5-nitro-4 '-(4-phenylbutoxy) benzanilide (Step 1, synthesis of compound 85 of the present invention) 5-nitrosalicylic acid 3.66 g (20.0 mmol) and 4-
A suspension of phenylbutoxyaniline (4.82 g, 20.0 mmol) in anhydrous toluene (25 ml) was heated under reflux, and a solution of phosphorus trichloride (1.37 g, 10.0 mmol) in anhydrous toluene (5 m) was added.
l) was added dropwise, and the mixture was heated under reflux for 2 hours. The residue obtained by concentrating the reaction mixture under reduced pressure was recrystallized from ethyl acetate to obtain 4.16 g (yield 51%) of pale yellow crystals.

Production Example 2 2-hydroxy-5- (trifluoromethyl) -4'-
(Phenoxymethyl) benzanilide (Step 1, synthesis of compound 97 of the present invention) 5- (trifluoromethyl) salicylic acid 2.00 g (9.
71 mmol) and 1.80 g of 4-benzylaniline (9.71)
mmol) in DMF solution (20 ml) at 0 °
To 5>, while stirring, N, N'-dicyclohexylcarbodiimide (2.00 g, 0.01 mol) of DMF was added.
The solution (10 ml) was added over 5 minutes. After stirring at the same temperature for 1 hour, the mixture was stirred at room temperature overnight. After the reaction mixture was filtered by suction, the filtrate was poured into ice water and extracted with ethyl acetate (x3). The organic layers were combined, washed with 0.5N hydrochloric acid and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was washed with ether, filtered and air-dried to obtain 2.88 g (yield 80%) of a white powder. Obtained.

Production Example 3 5-Cyano-2-hydroxy-4 '-(2-phenylethoxy) benzanilide (Step 2, synthesis of compound 88 of the present invention) 4- (phenylethoxy) aniline 1.30 g (5.7 mm)
ol) and triethylamine 0.83 g (8.25 mmol) in 1,2-dichloroethane solution (25 ml) under ice-water cooling,
5-Cyanosalicylic acid chloride 1.09 g (5.5 mmol)
1,2-dichloroethane solution (5 ml) was added dropwise over 20 minutes, and the mixture was further stirred for 2 hours. The reaction mixture was poured into ice water and extracted with chloroform.
The mixture was washed with 5N hydrochloric acid and saturated brine and dried over anhydrous magnesium sulfate. The residue obtained by concentrating the organic layer under reduced pressure was recrystallized from a mixed solvent of acetone and hexane to give a pale yellow powder 1.5.
0 g (77% yield) was obtained.

Production Example 4 2-acetoxy-3-iodo-5-nitro-4 '-(phenoxymethyl) benzanilide (Step 3, synthesis of compound 122 of the present invention) 2-hydroxy-3-iodo-5-nitro-4 '-(Phenoxymethyl) benzanilide 2.70 g (5.50 mm
ol), pyridine 1.30 ml (16.5 mmol) anhydrous TH
F solution (10 ml) under ice-water cooling, acetyl chloride 1.20
Anhydrous THF solution (5 ml) of ml (16.5 mmol) was added dropwise over 5 minutes, and the mixture was further stirred at the same temperature for 4 hours.
The reaction mixture was poured into ice water, and the generated precipitate was filtered off and washed with water. The crude crystals were dissolved in ethyl acetate and dried with anhydrous MgSO ₄ .
After concentration under reduced pressure, the residue was recrystallized from a mixed solvent of acetone and hexane to obtain 1.0 g of white powder (yield 34%).

Production Example 5 2-Hydroxy-5-nitro-4 '-(2-phenylethoxy) benzanilide sodium salt (Step 4, synthesis of compound 92 of the present invention) 2-Hydroxy-5-nitro-4'-( 2-Phenylethoxy) benzanilide 5.00 g (13.2 mmol) in anhydrous THF solution (50 ml) under ice-water cooling, 28% sodium methoxide methanol solution 2.60 g (13.5 mmol)
A mixture of 20 ml of anhydrous THF was added dropwise over 5 minutes, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure, the obtained residue was washed with a mixed solution of dry ether and acetone, and then the crystals were filtered off and air-dried to obtain 4.4 g (yield 85%) of a yellow powder.

The compounds of the present invention produced according to the methods shown in the above Production Examples are shown in Tables 1 to 7. Me in Tables 1-7
Represents methyl, Ac represents acetyl, and Ph represents phenyl.

[0034]

[Table 1]

[0035]

[Table 2]

[0036]

[Table 3]

[0037]

[Table 4]

[0038]

[Table 5]

[0039]

[Table 6]

[0040]

[Table 7]

The NMR spectrum data and the melting points of the compounds in Tables 1 to 7 are shown in Tables 8 to 20. Tables 8 to 20 solv
In ent, c is CDCl _3, d denotes a DMSO-d _6.

[0042]

[Table 8]

[0043]

[Table 9]

[0044]

[Table 10]

[0045]

[Table 11]

[0046]

[Table 12]

[0047]

[Table 13]

[0048]

[Table 14]

[0049]

[Table 15]

[0050]

[Table 16]

[0051]

[Table 17]

[0052]

[Table 18]

[0053]

[Table 19]

[0054]

[Table 20]

Formulation examples are shown below. In addition, a part represents a weight part. Formulation Example 1 Emulsion 10 parts of each of the compounds of the present invention were mixed with 35 parts of xylene and N,
It was dissolved in 35 parts of N-dimethylformamide, 14 parts of polyoxyethylene styryl phenyl ether and 6 parts of calcium dodecylbenzene sulfonate were added thereto, and the mixture was stirred and mixed to obtain a 10% emulsion of each.

Formulation Example 2 Wettable Powder 20 parts of each of the compounds of the present invention were added to a mixture of 4 parts of sodium lauryl sulfate, 2 parts of calcium ligninsulfonate, 20 parts of synthetic hydrous silicon oxide fine powder and 54 parts of diatomaceous earth, 20% wettable powder was obtained by stirring and mixing with a juice mixer.

Formulation Example 3 Granules Synthetic hydrous silicon oxide fine powder was added to 5 parts each of the compound of the present invention.
5 parts, sodium dodecylbenzenesulfonate 5 parts,
Bentonite (30 parts) and clay (55 parts) are added and mixed with sufficient stirring. Then, an appropriate amount of water is added to these mixtures, the mixture is further stirred, granulated by a granulator, and dried by ventilation to obtain 5%.
A granule was obtained.

Formulation Example 4 Dust agent 1 part of each of the compounds of the present invention was dissolved in an appropriate amount of acetone,
To this, 5 parts of synthetic hydrous silicon oxide fine powder, 0.3 part of PAP (isopropyl acid phosphate) and 93.7 parts of clay were added, and mixed by stirring with a juice mixer, and acetone was removed by evaporation to obtain a 1% powder. .

Formulation Example 5 Flowable Agent 20 parts each of the compound of the present invention, polyoxyethylene tristyrylphenyl ether phosphate triethanolamine 3 parts, propylene glycol 5 parts, RHODO
80 parts of water containing 0.2 part of RSIL 426R (silicone defoamer) and 0.32 part of xanthan gum was mixed and wet-ground using a dyno mill to obtain a 20% suspension in water.

Next, it will be shown by test examples that the compound of the present invention is useful as an active ingredient of a bactericide.

Test Example 1 Preventive effect against tomato epidemic disease The 20% flowable agent prepared in Formulation Example 5 was diluted with water to prepare 250 and 50 ppm drug solutions. 4th in the greenhouse
Tomatoes (cultivar: minicarol) grown to the age of leaves were sprayed with a chemical solution at a spray water volume of 10 ml / 2 pot. After leaving the tomato seedlings sprayed with the chemical at 20 ° C for 5 hours to volatilize the water, the tomato disease-causing fungus (phytophthora infes)
tans) zoosporangia suspension (2.2 × 10 ⁵ co / ml) was spray-inoculated on the tomato leaf surface at a spraying water amount of 3 ml / 2 pots. For 24 hours after the inoculation, leave it in an inoculation box kept at 20 ° C and 100% humidity to make it suitable for infection, and then at 24 ° C and humidity 9
It was transferred to the incubator kept at 5% to cause illness. Five days after the inoculation, the control effect was calculated from the diseased area according to the following criteria by comparing with the untreated section, and the results are shown in Tables 21 to 22.
It was shown to. As the control compound, 5,4 ′ of the structural formula (7) was used.
-Dibromo-2-hydroxybenzanilide (compound described in US Pat. No. 2,802,029) was used. A: Control value 100% B: Control value 99% to 81% C: Control value 80% to 50% D: Control value 49% to 0%

[0062]

[Chemical 6]

Test Example 2 Preventive effect against cucumber downy mildew The 20% flowable agent prepared in Formulation Example 5 was diluted with water to prepare 250 and 50 ppm drug solutions. Second in the greenhouse
10 ml of cucumber (cultivar: Sharp 1) grown on leaf age
The chemical solution was sprayed on the foliage with a spray water amount of / 2 pot. The tomato seedlings sprayed with the chemicals were left at 20 ° C for 5 hours to volatilize the water and then cucumber downy mildew (Pseudoperonospora c
ubensis) was spray-inoculated on the leaf surface of cucumber. For 24 hours after inoculation, leave it in an inoculation box kept at 20 ° C and 100% humidity to make it suitable for infection, and then at 24 ° C,
The disease was transferred to a thermostat kept at a humidity of 95% to cause illness. Fourteen days after the inoculation, the control effect was calculated from the diseased area according to the above-mentioned criteria by comparing with the untreated section, and the results are shown in Table 2.
1 to 22. As a control compound, 5,4'-dibromo-2-hydroxybenzanilide was used. Table 2
In 1 to 22, pi indicates tomato epidemics and pc indicates cucumber downy mildew.

[0064]

[Table 21]

[0065]

[Table 22]

[0066]

INDUSTRIAL APPLICABILITY The compound of the present invention is useful for a variety of diseases causing agricultural and horticultural problems, in particular, plant diseases caused by typical plant pathogens of flagellar fungi such as plague and downy mildew. Therefore, the compound of the present invention can provide a useful plant disease controlling agent.

 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Hiroshi Manabe 649-2 Satoura-cho, Satoura-cho, Naruto-shi, Tokushima Prefecture Naruto Research Institute, Otsuka Chemical Co., Ltd. (72) Keisuke Endo Satoura-cho, Satoura-cho, Naruto-shi, Tokushima Prefecture 649-2 Otsuka Chemical Co., Ltd. in Naruto Laboratory (72) Inventor Kazumi Sagayama 649-2 Satoura-cho, Satoura-cho, Naruto City, Tokushima Prefecture 649-2 Otsuka Chemical Co., Ltd. in Naruto Laboratory (72) Inoue Komura 649, Satoura-cho, Satoura-cho, Naruto City, Tokushima Prefecture -2 Naruto Laboratory, Otsuka Chemical Co., Ltd.

Claims (2)

[Claims] 1. A salicylic acid anilide derivative represented by the general formula (1). Embedded image [In the formula, R represents a hydrogen atom, a C _{1 to} C ₆ alkanoyl group, an alkali metal cation or an alkaline earth metal cation equivalent, or an ammonium cation which may be optionally mono- or polysubstituted with the same or different substituents. Represents a hydrogen atom, a halogen atom, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkoxy group, a formamide group, X represents a nitro group, a cyano group, a trifluoromethyl group, Y and Z is a hydrogen atom, a halogen atom, C _{1 to} C ₆
Represents an alkyl group, a C ₁ -C ₆ haloalkyl group, a phenyl group, an anilino group, a benzoyl group, A and B represent an oxygen atom and a sulfur atom, p and q represent an integer of 0 or 1, and m is 0 to Represents an integer of 4, and n represents an integer of 0 to 6. However, the case where X is a nitro group and both p and n are 0 is excluded. ] 2. A plant disease control agent comprising the salicylic acid anilide derivative according to claim 1 as an active ingredient.