JPH0558809A - Agricultural and horticultural fungicide - Google Patents

Abstract

PURPOSE:To obtain an agricultural and horticultural fungicide having high activity and safety, showing highly controlling effects on downy mildew, late blight, powdery mildew and rust, important disease damage of vegetables, fruits and grains, comprising a sulfonyl ketone derivative as an active ingredient. CONSTITUTION:An agricultural and horticultural fungicide comprising a sulfonyl phenyl ketone derivative shown by formula I [R<1> is H, CH3 or halogen; R<2> is lower alkyl or phenyl which may contain substituent group (halogen or lower alkyl); X is H or halogen] such as 1-(2-methoxy4-methylphenyl)-2- phenylsulfonylethanone as an active ingredient, having the above-mentioned effects. The compound is well-known as a color photographic sensitized material of silver halide and is readily produced by reacting a compound shown by formula II (R is lower alkyl) with a compound shown by formula III in the presence of a base in a solvent such as dimethyl sulfoxide.

Description

Detailed Description of the Invention

[0001]

[Object of the Invention]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an agricultural and horticultural fungicide containing a sulfonylphenyl ketone derivative represented by the following general formula (I) as an active ingredient.
Therefore, the present invention is useful in the chemical industry and the fields of agriculture and horticulture, especially in the field of agricultural chemicals production.

[0002]

2. Description of the Related Art It has been known that the compounds of the present invention have properties as a silver halide color photographic light-sensitive material (JP-A-54-48536). However, it is not known that the compound of the present invention has bactericidal activity.

[0003]

Various agents have been used so far for downy mildew, plague, powdery mildew, rust, etc., which are important diseases of fruit trees, vegetables, and cereals. Due to problems such as resistance, it is no longer possible to use, or its use has been restricted. Therefore, in these fields, the emergence of new fungicides having a skeleton different from that of conventional drugs has become a major problem, and the present invention aims to solve these problems.

[0004]

[Constitution of the invention]

[Means for Solving the Problems] The inventors of the present invention have synthesized a number of compounds in order to achieve the above object, and have made earnest studies on their usefulness. As a result, they have found that the sulfonylphenyl ketone derivative represented by the following general formula (I) has high activity and safety as a fungicide for agricultural and horticultural use.

Therefore, the gist of the present invention is to
The following general formula (I)

[Chemical 2] (In the formula, R ¹ represents a hydrogen atom, a methyl group or a halogen atom, R ² represents a lower alkyl group, a phenyl group or a phenyl group substituted with a halogen atom or a lower alkyl group, and X represents a hydrogen atom. Or a sulfonylphenyl ketone derivative represented by a halogen atom) as an active ingredient.

Next, Table 1 shows specific examples of the compound of the present invention of the general formula (I).

The compound No. is also referred to in the following examples and test examples.

[0008]

[Table 1]

[0009]

The compound of general formula (I) acts as an active ingredient of an agricultural and horticultural fungicide.

[Examples] (Method for producing compound of the present invention) The compound of the general formula (I) according to the present invention can be easily produced by a known method.

That is, 2-methoxy-4-methylbenzoic acid esters represented by the general formula (II) and the general formula (II
It can be produced by reacting the sulfone represented by I) in the presence of a base in a solvent such as dimethyl sulfoxide.

[0012]

[Chemical 3] (In the formula, R ¹ , R ² and X have the same meaning as described above, and R represents a lower alkyl group.)

The solvent used in this reaction includes dimethyl sulfoxide, dimethylformamide, dimethylacetamide and the like. As the base, alkoxides such as sodium hydride, potassium hydride, potassium t-butoxide, sodium hydroxide, potassium hydroxide and the like can be used.

Although the reaction proceeds even at room temperature, the reaction time can be shortened by heating in the range up to the boiling point of the solvent.

[0015]

[Chemical 4] The compound of the general formula (I) in which R ¹ is halogen can be produced by halogenating the compound produced by the above reaction formula in which R ¹ is hydrogen with a suitable halogenating agent. As the halogenating agent, chlorine, bromine, iodine, sulfuryl chloride or the like can be used.

As the reaction solvent, water, alcohols such as acetic acid, methanol and ethanol, and halogenated hydrocarbons such as chloroform and dichloromethane can be used.

The reaction can be carried out in the range of 0 ° C. to the boiling point of the solvent.

Production examples by these methods are shown in Examples 1-2.
It was shown to.

Example 1 Preparation of 1- (2-Methoxy-4-methylphenyl) -2-phenylsulfonylethanone (Compound No. 5) A mixture of 15.6 g of methylphenyl sulfone and 200 ml of dimethyl sulfoxide was cooled with water. 4 g of 60% sodium hydride was added, and the mixture was gradually heated and treated with 2-methoxy- at 50 ° C.
18 g of methyl 4-methylbenzoate was added dropwise. 70 after dropping
Stir at ℃ for 1 hour, add to ice water, acidify with hydrochloric acid,
The precipitate was collected by filtration. The crystals were washed with water, dried, and recrystallized from toluene and n-hexane to give 25.1 g of the title compound as colorless crystals, which had a melting point of 111-113 ° C.

Example 2 2-Bromo-1- (2-methoxy-4-methylphenyl) -2-methylsulfonylethanone (Compound No.
3) Preparation of 1- (2-methoxy-4-methylphenyl) -2-methylsulfonylethanone (24.2 g) in chloroform (50 m)
l, dissolved in a mixed solvent of 50 ml of acetic acid, bromine 16 under ice cooling
g was added dropwise. After dropping, the mixture was stirred at room temperature for 1 hour, added to ice water and extracted with chloroform, the organic layer was washed with water, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 31 g of the title compound as light brown crude crystals.
Recrystallization from toluene-n-hexane gave a melting point of 57-
It showed 60 ° C.

[Example] (Method for formulating agricultural / horticultural fungicide) The agricultural / horticultural fungicide of the present invention can be used by formulating the compound of the general formula (I) by a conventional formulation.
That is, a compound of the general formula (I) and a suitable carrier and auxiliary agent, for example, a surfactant, a binder, a stabilizer and the like are mixed to prepare a wettable powder, an emulsion, a liquid agent, a sol agent (flowable agent),
It may be formulated as an oil agent, a powder agent, a DL (driftless type) powder agent, a fine powder agent, a coarse powder agent, a granule agent and the like. The content of the compound of the present invention in these formulations is a wettable powder, an emulsion, a sol,
In the case of an oil agent, the range is 1 to 90% (% by weight: the same applies hereinafter),
0.5 to 5 for powders, DL powders, fine powders, and coarse powders
%, And in the case of granules, it can be contained in the range of 1 to 10%.

The method of using the agricultural / horticultural germicide of the present invention is generally as follows.

That is, in the case of a wettable powder, a liquid preparation, an emulsion, a sol preparation (flowable preparation) and an oil preparation, 500 to 20 with water.
Generally diluted 1 to 10,000 pp with active ingredient diluted to 100 times
It is adjusted to a concentration of m. And for every 10 are, 50-500 liters of this diluent, usually 100-300
It is sprayed on the foliage at the disease occurrence site of the plant in the range of 1 liter.

Liquid solutions, emulsions and sol agents (flowable agents) are not diluted with water and remain as a concentrated solution or 10 times with water.
Dilute within a factor of 2 and use it as a micro-spraying agent (LV
As a spraying agent, ULV spraying agent) 50 per 10 are
A volume of 3000 ml is sprayed using a helicopter.

The powder, DL powder, fine powder and coarse powder are 2 to 5 kg per 10 ares (50 to 5 as active ingredient).
(Approx. 00 g) is applied to the foliage of the diseased part of the plant, the soil surface, the soil or the water surface.

The method of formulating the compound of the present invention of the general formula (I) as an agricultural and horticultural fungicide is described in Example 3 below.
~ 6.

Example 3 (powder) 2 parts of compound No. 8, PAP (physical property improver)
1 part and 97 parts of clay are mixed uniformly and ground to give a dust containing 2% of active ingredient.

Example 4 (Wettable powder) 20 parts of the compound of compound No. 10, 3 parts of potassium alkylbenzene sulfonate, 5 parts of polyoxyethylene nonylphenyl ether and 72 parts of clay were uniformly mixed and pulverized. A wettable powder containing 20% of the active ingredient is obtained.

[Example 5] (Emulsion) 30 parts of compound No. 3 and methyl ethyl ketone 4
When 0 part and 30 parts of polyoxyethylene nonylphenyl ether are mixed and dissolved, an emulsion containing 30% of the active ingredient is obtained.

Example 6 (Sol Agent) 40 parts of the compound of compound No. 9, 2 parts of lauryl sulfate, 2 parts of sodium alkylnaphthalene sulfonate, 2 parts of acetoxypropyl cellulose and 55 parts of water were uniformly mixed, A sol containing 40% of active ingredient is obtained.

[0031]

The compound of the present invention exhibits a high control effect against downy mildew, plague, powdery mildew, and rust, which are important diseases of fruit trees, vegetables, and cereals, and therefore, as a fungicide for agricultural and horticultural use. It is useful.

Next, the usefulness and specific examples of the compound of the present invention represented by formula (I) are shown in Test Examples 1 and 2.

[Test Example 1] Cucumber downy mildew control effect test Second test in which soil was cultivated in a greenhouse in a clay pot with a diameter of 9 cm
To a cucumber seedling (variety: Sagamihanjiro) at the leaf stage, 20 ml of a predetermined concentration of a wettable powder prepared according to Example 4 was sprayed per pot. Then, with a moistened brush, cucumber downy mildew ( Pseu
Doperonospora cubensis : Pseudoperonospora cubensis ) was scraped off from spores and suspended in a 50 ppm aqueous solution of a spreading agent (polyoxyethylene alkyl ether). Then, the spore concentration was adjusted to 5 × 10 spores (piece / ml), and one day after spraying the drug, a spore suspension of cucumber downy mildew was spray-inoculated. And 20 ℃, 100%
Then, the cucumber downy mildew was developed by allowing it to stand in the greenhouse for 2 days. Six days after the inoculation, the cucumber downy mildew diseased lesion area ratio (%) per leaf was calculated, the control value (%) was calculated by the following formula, and the evaluation value was calculated according to the following criteria.

This test was carried out in duplicate for each concentration of the chemical solution. In addition, phytotoxicity to cucumber was investigated according to the following criteria. The results are shown in Table 2.

The evaluation value of the bactericidal effect and the investigation index of drug damage were similarly used in the following Test Example 2.

[0036]

[Equation 1]

[0037]

[0038]Survey index of drug damage  5: Extreme 4: Strong 3: Many 2: Only 1: None

[0039]

[Table 2] Note) The figures in parentheses () in non-scattered plots indicate the average lesion area rate per leaf. Comparative drug A

[Chemical 5]

[Test Example 2] Wheat leaf rust control effect test No. 1 cultivated in soil in a greenhouse in a clay pot with a diameter of 9 cm
20 ml of a predetermined concentration diluting solution of a wettable powder prepared according to Example 4 was added to a wheat seedling (variety: No. 61) in the leaf stage per 3 pots.
Was sprayed. After one day in advance of wheat brown rust which has formed on wheat leaves (Puccinia recondita: Pukushinia recondita) Tween 20 [Kao to the summer spores spore concentration per field at 150 power microscope of about 50 (strain Trade name of polyoxyethylene sorbitan monolaurate manufactured by
The spore suspension was spray inoculated onto the leaves to be treated. 20
After keeping it in a greenhouse at 100 ° C and humidity of 100% overnight, it was transferred in a greenhouse at 20 ° C to promote disease onset. Remove 10 days after inoculation,
The number of summer spore stacks infected per leaf was investigated to obtain the average number of summer spore stacks, and the control value (%) was calculated by the following formula, and converted into an evaluation value of the bactericidal effect in the same manner as in Test Examples.

This test was carried out in a system of three pots per concentration of one drug solution. In addition, the degree of phytotoxicity to wheat was investigated and displayed according to the same criteria as in Test Example 1. The results are shown in Table 3.

[0042]

[Equation 2]

[0043]

[Table 3] Note) The number in parentheses in the non-scattering plot indicates the number of lesions per leaf. Comparative drug B

[Chemical 6]

 ─────────────────────────────────────────────────── ─── Continuation of front page (72) Inventor Kazuo Kajikawa 2385 Toda, Atsugi City, Kanagawa Prefecture

Claims (1)

[Claims] 1. A general formula: (In the formula, R ¹ represents a hydrogen atom, a methyl group or a halogen atom, R ² represents a lower alkyl group, a phenyl group or a phenyl group substituted with a halogen atom or a lower alkyl group, and X represents a hydrogen atom. Or a sulfonylphenyl ketone derivative represented by a halogen atom) as an active ingredient.