JPH0995489A - Isonicotinic acid derivative and agricultural and horticultural fungicide - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a new isonicotinic acid derivative useful as an agricultural and horticultural fungicide, showing highly controlling effect on blast of rice plant, sheath blight of rice plant, powdery mildew, downy mildew, etc. SOLUTION: This compound is shown by formula I (X is a halogen; Y and Z are each oxygen atom, sulfur atom, etc.; A is a lower alkyl and is a monosubstituted or disubstituted 1-6C alkylene; (n) is 0-2; B is H, a lower alkyl, etc.; (m) is 1-3) such as N-(2,6-dichloroisonicotinyl)-2-(6-methyl-2-pyridyl)-4-n- propyl-6-pyrimidinyloxydiethylamine. The compound, for example is obtained by reacting an isonicotinic acid derivative of formula II with a methanesulfonylpyrimidine derivative of formula III in the presence of a deoxidizer such as triethylamine, etc., in an organic solvent such as tetrahydrofuran, etc. The reaction temperature is preferably 20-80 deg.C. The compound of formula III is a new substance and is preferably obtained by oxidizing methylthiopyrimidine.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a novel isonicotinic acid derivative. More specifically, the isonicotinic acid derivative represented by the general formula (1) described below, a fungicide for agricultural and horticultural use containing the derivative as an active ingredient, and a novel methane suitable for use in producing the isonicotinic acid derivative. A sulfonylpyrimidine derivative. Therefore,
INDUSTRIAL APPLICABILITY The present invention is useful in the chemical industry and the fields of agriculture and horticulture, particularly in the field of agricultural chemicals manufacturing.

[0002]

BACKGROUND OF THE INVENTION Several isonicotinic acid derivatives which are similar in chemical structure to the compounds of the present invention have been known so far,
All are known to have bactericidal activity.

For example, JP-A-55-143969 discloses that an isonicotinic acid derivative represented by the following general formula has herbicidal activity.

[0004]

Embedded image(In the formula, Z represents Br or Cl, and R Is OH, N
H₂, NH-lower alkyl or NH-phenyl, etc.
R'is H or CH_Three, And X is C (C
H_Three)₂, (CH₂) N, etc., where n is an integer from 2 to 5
Or the moiety contained in Y is a naturally occurring amino acid
Represents an acyl moiety. )

Further, JP-A-4-124177 discloses that an isonicotinic acid derivative represented by the following general formula has bactericidal activity.

[0006]

Embedded image (In the formula, W represents a group —NNHHR ¹ or a group —OR ² .
R ₁ is a group

[Chemical 6]Group -COOR^ThreeEtc. (However, in the group, X and Y are
Independently a hydrogen atom, a halogen atom or a lower alkyl group
Show. ) And R²Is an alkyl group, a propargyl group,
Group-CH₂CH₂OR^FourAnd R^Three Represents a lower alkyl group
Then R^FourIs a hydrogen atom, a lower alkyl group or a lower alkyl group.
Represents a carbonyl group. )

[0007]

However, the compounds described in these documents have insufficient bactericidal activity against diseases in the field of agriculture and horticulture or cause phytotoxicity to crops, as shown in Test Examples below. Therefore, it is hard to be satisfied practically.
On the other hand, rice blast, which is an important disease of fruit trees, vegetables, and cereals,
Various chemicals have been used for rice blight, powdery mildew of vegetables, downy mildew, gray mold, etc.
In all fields, resistant bacteria have become a problem, and there is a tendency that drugs cannot be used or their use is limited. Therefore, in these fields, new agricultural and horticultural fungicides having a skeleton different from that of conventional drugs are desired. An object of the present invention is to provide an agricultural and horticultural fungicide meeting these needs.

[0008]

Means for Solving the Problems The present inventors have synthesized many compounds in order to achieve the above-mentioned object, and have intensively studied their usefulness. As a result, they have found that an isonicotinic acid derivative represented by the following general formula (1) has high activity as an agricultural and horticultural fungicide.

Therefore, the gist of the first aspect of the present invention lies in the following general formula (1):

[Chemical 7](In the formula, X represents a halogen atom, and Y and Z are
Each of them may be different from each other, and an oxygen atom, a sulfur atom or
Is NR Represents a group, and A is a monoalkyl or lower alkyl group.
Represents a di-substituted C1-C6 alkylene group, n
Is an integer of 0, 1 and 2, where R Is a hydrogen source
Child, lower alkyl group, and B may be different from each other.
Hydrogen atom, lower alkyl group, lower haloalkyl group,
A lower alkoxy group or a lower alkylamino group
Or halogen atom, lower alkyl group, lower haloalkyl
Group or phenyl optionally substituted with a lower alkoxy group
Group or pyridyl group, m represents an integer of 1 to 3
You. ) In the isonicotinic acid derivative.

The gist of the second aspect of the present invention is an agricultural and horticultural fungicide characterized by containing the isonicotinic acid derivative of the general formula (1) as an active ingredient.

Further, they have found a methanesulfonylpyrimidine derivative which is preferably used in the production of the compound of formula (1).

Therefore, the gist of the third invention is that the general formula is

Embedded image (In the formula, B may be different from each other and is a hydrogen atom, a lower alkyl group, a lower haloalkyl group, a lower alkoxy group or a lower alkylamino group, a halogen atom, a lower alkyl group, a lower haloalkyl group or a lower alkoxy group. Represents a phenyl group or a pyridyl group which may be substituted with m, and m represents an integer of 1 to 3).

In the compound represented by the general formula (1),
R , A and B, and compounds represented by the general formula (3)
In the definition of B, lower alkyl group, lower alcohol
Xy, lower haloalkyl and lower alkylamino
The group may be linear or branched. Also here
The term "lower" means one having 1 to 6 carbon atoms.

Examples of the lower alkyl group of lower alkyl group and lower alkylamino group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group,
t-butyl group, isobutyl group, sec-butyl group, n-
There are a pentyl group, an isoamyl group, an n-hexyl group and the like, and examples of the lower haloalkyl group include a trifluoromethyl group, a difluoromethyl group, a trichloromethyl group, a dichloromethyl group, a fluoromethyl group, a chloromethyl group,
There are iodomethyl group, bromomethyl group, pentafluoroethyl group, pentachloroethyl group and the like, and examples of the lower alkoxy group include methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, sec.
Examples include -butoxy group, t-butoxy group, isobutoxy group, and isohexyloxy group.

Specific examples of the compound of the present invention represented by the general formula (1) are shown in Tables 1 to 3.

Compound No. Is also referred to in the following Examples and Test Examples.

[0017]

[Table 1]

[0018]

[Table 2]

[0019]

[Table 3]

[0020]

BEST MODE FOR CARRYING OUT THE INVENTION Method for Producing Compound of the Present Invention The compound of the general formula (1) according to the present invention can be produced by either method (A) or method (B).

First, the method (A) will be specifically described.

General formula

Embedded image (Wherein X, Y, Z, A and n have the same meanings as described above), and the isonicotinic acid derivative represented by the general formula

Embedded image (In the formula, B and m have the same meanings as described above.) By reacting with a methanesulfonylpyrimidine derivative represented by the general formula

Embedded image (In the formula, X, Y, Z, A, B, n and m have the same meanings as described above.) The compound of the present invention can be obtained.

General formula as a starting material in the method (A)

[Chemical 12] (In the formula, X, Y, Z, A and n have the same meanings as described above.) The compound of formula (2) is a known substance,
Known methods, for example, the general formula

Embedded image (In the formula, X and n have the same meanings as described above, and Hal represents a halogen atom.) And an isonicotinic acid halide represented by the general formula

Embedded image (In the formula, Y, Z and A have the same meanings as described above.) The compound can be produced by reacting.

Formula (4), which is the starting material for the compound of Formula (2),
(5) The compound is a known substance.

The general formula of the compound of the following formula (3) which is a starting material

[Chemical 15] The methanesulfonylpyrimidine derivative represented by the formula (wherein B and m have the same meanings as described above) is a novel compound and is a journal of organic chemistry.
48) 4841 to 4843 (1)
It can be produced by oxidizing methylthiopyrimidine obtained by the method described in 983).

The compound of formula (3) thus obtained may be directly reacted with the compound of formula (2) without isolation.

Example 3 shows a production example of the compound of the formula (3).

Specific examples of the compound of formula (3) are shown in Tables 4-5.

[0029]

[Table 4]

[0030]

[Table 5]

Next, the specific method for producing the compound of formula (1) by the method (A) will be described in more detail.

In the method (A), the step of reacting the compound of formula (2) with the compound of formula (3) to obtain the compound of formula (1) uses an equal amount of each reaction component, The reaction is carried out in a suitable organic solvent in the presence of 1 to 2 equivalents of a deoxidizing agent.

The reaction temperature is close to the boiling point of the organic solvent,
The temperature is preferably 20 to 80 ° C., and the reaction is carried out by stirring the reaction mixture for 1 to 3 hours.

Examples of the deoxidizing agent include organic bases such as triethylamine, pyridine and N, N-diethylaniline, and inorganic bases such as sodium hydroxide, potassium hydroxide, sodium hydride, sodium carbonate, sodium hydrogen carbonate and potassium carbonate. Can be used.

As the organic solvent, benzene, toluene,
Hydrocarbons such as xylene, halogenated hydrocarbons such as chloroform, dichloromethane, chlorobenzene, ethers such as ethyl ether, dioxane, and tetrahydrofuran; nitriles such as acetonitrile and propionitrile; amides such as dimethylformamide and dimethylacetamide And dimethyl sulfoxide can be used.

After completion of the reaction, water and an organic solvent such as benzene, toluene and chloroform are added to the reaction solution to separate the solution,
After dehydration with anhydrous sodium sulfate, anhydrous magnesium sulfate, etc., a usual treatment such as distilling off the solvent is carried out, and if necessary, purification may be carried out by operations such as chromatography and recrystallization.

An example of production by the method (A) is shown in Example 1.

Next, the method (B) will be specifically described.

General formula

Embedded image (In the formula, Y, Z, A, B and m have the same meanings as described above.)

Embedded image (In the formula, X and n have the same meanings as described above, and Hal represents a halogen atom.) By reacting with an isonicotinic acid halide represented by the general formula

Embedded image (In the formula, X, Y, Z, A, B, n and m have the same meanings as described above.) The compound of the present invention can be obtained.

General formula as a starting material in the method (B)

Embedded image (Wherein Y, Z, A, B and m have the same meanings as described above), and the pyrimidine derivative represented by the general formula is

Embedded image (In the formula, B and m have the same meanings as described above.) And a methanesulfonylpyrimidine derivative represented by the general formula

[Chemical 21] (In the formula, Y, Z and A have the same meanings as described above.) The compound can be produced by reacting.

The compounds of formula (5) and formula (6) are known substances and can be obtained by known methods. Further, the compound of formula (3) can be obtained by the method described above.

Next, the specific method for producing the compound of formula (1) according to method (B) will be described in more detail.

In the method (B), in the step of reacting the compound of formula (4) with the compound of formula (6) to obtain the compound of formula (1), an equivalent amount of each reaction component is used to give a compound of formula (4). On the other hand, the reaction is carried out in a suitable organic solvent in the presence of 1 to 2 equivalents of a deoxidizing agent.

The reaction temperature is close to the boiling point of the solvent, preferably 20 to 80 ° C., and the reaction is carried out by stirring the mixture for 1 to 3 hours.

As the deoxidizing agent, organic bases such as triethylamine, pyridine and N, N-diethylaniline, and inorganic bases such as potassium hydroxide, sodium hydride, sodium carbonate, sodium hydrogen carbonate and potassium carbonate can be used.

As the organic solvent, benzene, toluene,
Hydrocarbons such as xylene, halogenated hydrocarbons such as chloroform, dichloromethane, chlorobenzene, ethers such as ethyl ether, dioxane, and tetrahydrofuran; nitriles such as acetonitrile and propionitrile; amides such as dimethylformamide and dimethylacetamide And dimethyl sulfoxide can be used.

After completion of the reaction, water and an organic solvent such as benzene, toluene and chloroform are added to the reaction solution to separate the solution,
After dehydration with anhydrous sodium sulfate, anhydrous magnesium sulfate, etc., a usual treatment such as distilling off the solvent is carried out, and if necessary, purification may be carried out by operations such as chromatography and recrystallization.

An example of production by the method (B) is shown in Example 2.

Example 1 N- (2,6-dichloroisonicotinyl) -2- (6-methyl-2-pyridyl) -4-
Production of n-Propyl-6-pyrimidinyloxyethylamine (Compound No. (1) -25) <Method (A)> N- (2,6-
Dichloroisonicotinyl) hydroxyethylamine 2
3.5 g, 2- (6-methyl-2-pyridyl) -4-n
-Propyl-6-methanesulfonylpyrimidine 29.
1 g (1 equivalent), potassium carbonate 13.8 g (1 equivalent)
Then, 250 ml of dimethylformamide was added, heated with stirring, and reacted at 65 ° C. for 1 hour. After cooling,
The reaction solution was put into water and extracted with chloroform, the organic layer was washed with water and dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure, and silica gel column chromatography (developing solvent: hexane: ethyl acetate = 10:
Purified by 1), 19.7 g of the title compound (yield 68
%) As brown crystals (mp 155 to 156.5 ° C.).

Example 2 2- (6-Methyl-2-pyridyl) -4-n-propyl-6-pyrimidinyloxyethyl-2,6-dichloroisonicotinate (Compound No.
Production of (1) -13) <Method (B)> In a four-necked flask having a capacity of 500 ml, 27.3 g of 2- (6-methyl-2-pyridyl) -4-n-propyl-6-pyrimidinyloxyethanol, Triethylamine
10.1 g (1 equivalent) and chloroform 200 ml
Then, 21.0 g (1 equivalent) of 2,6-dichloroisonicotinic acid chloride was added under ice-cooling with stirring. Thereafter, the mixture was stirred at room temperature for 2 hours. After completion of the reaction, the reaction mixture was put into water, the organic layer was washed with water, and dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure,
Purification by silica gel column chromatography (developing solvent: toluene-acetone = 15: 1) gave 41.1 g (yield 92%) of the title compound as white crystals (mp.8).
3 to 84 ° C.).

Example 3 Preparation of 2- (6-methyl-2-pyridyl) -4-n-propyl-6-methanesulfonylpyrimidine (Compound No. (3) -10) In a 500 ml four-necked flask, 6-methyl-2-
Picoline amidine 17.6 g, oily sodium hydride 4.0 g (1 equivalent), benzene 200 ml, and dimethylformamide 40 ml were added, and 3,3-bis (methylthio) -1-propyl-2-propene-was stirred at room temperature. 1-one (19.0 g, 1 equivalent) was added, and the mixture was reacted under reflux with heating for 24 hours. After completion of the reaction, the reaction mixture was put into water and extracted with chloroform, the organic layer was washed with water and dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure to obtain crystals of 2- (6-methyl-2-pyridyl) -4-n-propyl-6-methylthiopyrimidine. 26.0 g of the crystals, 24.0 g of acetic acid (3 equivalents) and 200 ml of acetone were added to a 500 ml four-necked flask, and 21 g (1 equivalent) of potassium permanganate was added with stirring at room temperature. afterwards,
Stir for 3 hours at room temperature.

After toluene and water were added to the reaction mixture, the insoluble material was filtered off, the organic layer was washed with water and dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure, and 18.0 g (yield 62%) of the title compound was obtained as pale yellow crystals (mp. 1).
09-112 ° C).

[0053]

BEST MODE FOR CARRYING OUT THE INVENTION A method for formulating an agricultural and horticultural fungicide The agricultural and horticultural fungicide according to the second aspect of the present invention is prepared by formulating the compound of the general formula (1) by a conventional formulation before use. You can That is, a compound generally used as a pesticide formulation can be prepared by blending the compound of the general formula (1) with an appropriate carrier and auxiliary agents such as a surfactant, a binder, and a stabilizer. For example, powder, coarse powder,
DL (driftless type) powder, flow dust, fine granule, fine granule, granule, wettable powder, sol (flowable),
It can be formulated into hydrated granules, emulsions and oils. The dosage forms that can be formulated are not limited to those listed here.

The amount of the compound of the present invention to be added can be appropriately changed depending on the dosage form of the preparation and the method of use, and is generally 0.1 to 0.1%.
It is desirable to use in the formulation in the range of 90% by weight.

The method of using the agricultural / horticultural germicide of the present invention is generally as follows. That is, in the case of wettable powders, emulsions, solutions, sol agents (flowable agents), hydrated granules and oil agents, the active ingredient is generally diluted to a concentration of 1 to 10000 ppm by diluting with water 50 to 2000 times. Is prepared.
Then, the diluted solution is sprayed onto the foliage at the disease occurrence site of the plant in an amount of 50 to 300 liters, usually 100 to 200 liters, per 10 ares.

Further, liquid solutions, emulsions and sol agents (flowable agents) are not diluted with water and remain as a concentrated solution or with water.
Dilute to within 0 times and use it as a microspraying agent (L
50 per 10 are as V spray and ULV spray)
~ 300ml is sprayed using a helicopter.

Further, powder, coarse powder, DL powder, flow dust, fine granule, fine granule and granule are 2 to 10 ares.
5 kg (about 5 to 500 g as the amount of active ingredient) is applied to the foliage of the disease occurrence site of the plant, the soil surface, the soil or the water surface.

The method of formulating the compound of the present invention represented by the general formula (1) as an agricultural and horticultural fungicide is described in Example 4 below.
~ 8.

Example 4 (Powder) Compound No. (1) -16 parts of the compound of -16, 1 part of PAP (physical property improver) and 97 parts of clay are uniformly mixed and pulverized to obtain a dust containing 2% of the active ingredient.

Compound No. Instead of (1) -16, Table 1
~ A powder can be similarly obtained using the compounds described in Table 3.

Example 5 (Wettable powder) Compound No. (1) -20 parts of a compound, 3 parts of potassium alkylbenzene sulfonate, 3 parts of polyoxyethylene nonylphenyl ether and 72 parts of clay were uniformly mixed and pulverized to obtain a wettable powder containing 20% of an active ingredient. obtain.

Compound No. (1) -5 in place of Table 1
A wettable powder can be similarly obtained by using the compounds shown in Table 3.

Example 6 (Emulsion) Compound No. 30 parts of the compound of (1) -9, 40 parts of methyl ethyl ketone and 30 parts of polyoxyethylene nonylphenyl ether were mixed and dissolved to give 30 parts of the active ingredient.
% To obtain an emulsion.

Compound No. (1) Instead of -9, Table 1
Emulsions can be similarly obtained using the compounds shown in Table 3.

Example 7 (sol agent) Compound No. (1) -25 compounds 40 parts, lauryl sulfate 2 parts, sodium alkylnaphthalene sulfonate 2 parts, acetoxypropyl cellulose 1 part and water 55
The parts are mixed uniformly to give a sol containing 40% of the active ingredient.

Compound No. Instead of (1) -25, Table 1
~ A sol can be similarly obtained using the compounds shown in Table 3.

Example 8 (Granule) Compound No. 10 parts of the compound of (1) -13, 1 part of lauryl sulfate, 5 parts of calcium lignin sulfonate,
30 parts of bentonite and 54 parts of clay are mixed with 15 parts of water and kneaded by a kneader, then granulated by a granulator and dried by a fluid dryer to obtain a granule containing 10% of an active ingredient.

Compound No. Instead of (1) -13, Table 1
~ Granules can be similarly obtained using the compounds described in Table 3.

[0069]

EFFECTS OF THE INVENTION The compound of the present invention has a high control effect against rice blast, rice blight, powdery mildew, downy mildew, plague, gray mold, etc. which are important diseases of cereals. Therefore, it is useful as a germicide for agriculture and horticulture.

Next, a specific example of the usefulness of the compound of the present invention is shown in Test Example 1.

Test Example 1 Rice Blast Control Effect Test Prepared in accordance with Example 5 on the third leaf stage seedling of paddy rice (cultivar: Asahi) cultivated in a greenhouse in a plastic pot having a diameter of 6 cm. 10 ml per pot of the wettable powder diluted with a predetermined concentration was sprayed using an automatic spraying device. The day after the drug treatment, the rice blast fungus ( Pyricularia ory) previously formed on an oatmeal agar medium was used.
zae : Pyroclaria oryzae) conidia (50 ppm of spreading agent (polyoxyethylene alkyl ether))
The spore concentration was adjusted to 5 × 10 ⁵ spores (number) / ml with an aqueous solution, and this was spray-inoculated using a spray gun. Two
After being kept in an inoculation box at 4 ° C. and 100% humidity overnight, they were transferred to a greenhouse at 24 ° C. to promote disease. 5 days after inoculation, one of the third leaves
The number of rice blast spots per leaf was investigated, and the control value (%) was calculated by the following equation.

This test was carried out in a 3-pot system per concentration of one chemical solution, the average control value (%) was determined, and converted into an evaluation value according to the following criteria. In addition, phytotoxicity to rice was investigated according to the following criteria. The results are shown in Table 6.

The evaluation value of the control effect and the investigation index of the chemical damage were similarly used in the following Test Examples 2 to 8.

[0074]

[Equation 1]

[0075]

[0076]

[Table 6]

[0077]

Embedded image Comparative compound A (Compound described in JP-A-55-143969)

[0078]

Embedded image Comparative compound B (Compound described in JP-A-4-124177)

Test Example 2 Rice blast water surface application effect test As a 5th leaf stage seedling of paddy rice (cultivar: Asahi) cultivated in a greenhouse in a Wagner pot with a size of 1/10000 ares under a flooding condition (water depth 3 cm). The granules prepared according to Example 8 were sprayed at 3 kg per 10 ares. 7 days after drug treatment,
The conidia of rice blast fungus ( Pyricularia oryzae ) previously formed on an oatmeal agar medium were condensed with a 50 ppm aqueous solution of a spreading agent (polyoxyethylene alkyl ether) to a spore concentration of 5 × 10 ⁵ spores. ) / Ml and spray inoculated with a spray gun. 24 ° C, humidity 1
After being kept overnight in a 00% inoculation box, they were transferred to a greenhouse at 24 ° C. to promote disease. Five days after the inoculation, the number of rice blast spots per leaf was examined, and the control value (%) was calculated in the same manner as in Test Example 1.

This test is conducted in a three-pot system per drug group,
In the same manner as in Test Example 1, the evaluation value of the control effect and the degree of chemical damage to rice were displayed. The results are shown in Table 7.

[0081]

[Table 7]

Test Example 3 Rice Blast Disease Seedling Box Treatment Effect Test Seedling raising box in the greenhouse (length x width x height: 60 cm x 30 cm x
For each 2.5-leaf stage seedling of paddy rice (variety: Asahi) cultivated at 5 cm), 50 granules per box prepared according to Example 8 were used.
g. One day after drug treatment, this was reduced to 1/10000
Five seedlings per pot were transplanted to a Wagner pot having a size of Earl and cultivated under flooded conditions (water depth: 3 cm). Transplant 30
Days later, rice blast fungus ( Pyricularia oryza) previously formed on an oatmeal agar medium
e : Conidia of Pyricularia oryzae) was adjusted to a concentration of 5 × 10 ⁵ spores (ml) / ml with a 50 ppm aqueous solution of a spreading agent (polyoxyethylene alkyl ether), and this was sprayed using a spray gun. Spray inoculated. 24
After being kept in an inoculation box at 100 ° C. and 100% humidity overnight, they were transferred to a greenhouse at 24 ° C. to promote the onset of the disease. Five days after the inoculation, the number of rice blast spots per leaf was examined, and the control value (%) was calculated in the same manner as in Test Example 1.

This test was carried out in a 5-pot system per drug group,
The evaluation value of the control effect and the degree of phytotoxicity to rice were displayed. Table 8 shows the results.

[0084]

[Table 8]

Test Example 4 Rice crest blight effect test A 6-7 leaf stage rice seedling (variety: Asahi) cultivated in a greenhouse in a plastic pot having a diameter of 6 cm was hydrated according to Example 5. 10 ml per pot was sprayed with a predetermined concentration diluted solution of the agent using an automatic spraying device. The day after the chemical treatment, the rice sheath blight fungus ( Rhi
zocontia solani : Rhizoctonia solani ) was placed at the strain as an inoculum. 24 ° C, humidity 100
% Rice plants were allowed to stand for 5 days to cause rice blight. Five days after the inoculation, the lesion length of the diseased leaf sheath was measured, and the control value (%) was calculated by the following formula.

This test was carried out in a 3-pot system for each chemical solution concentration, and the average control value (%) was determined and converted into an evaluation value of the control effect in the same manner as in Test Example 1. Further, phytotoxicity to the rice was investigated and displayed according to the same criteria as in Test Example 1. Table 9 shows the results.

[0087]

[Equation 2]

[0088]

[Table 9]

Test Example 5 Barley Powdery Mildew Control Effect Test No. 1 of barley (variety: Azuma Golden) cultivated in a greenhouse in a plastic pot with a diameter of 6 cm.
To the leaf stage seedlings, 10 ml per pot was sprayed with a predetermined concentration diluted solution of the wettable powder prepared according to Example 5. The day after the chemical treatment, barley powdery mildew ( Eryshiphe gra) was formed on barley leaf in advance.
minis : Erysiphe graminis) conidia spore spreader (polyoxyethylene alkyl ether) 50p
The spore concentration is 5 × 10 ⁵ spore count (pieces) / m
It was adjusted to 1 and this was spray-inoculated on the foliage of barley using a spray gun. After being kept in an inoculation box at 20 ° C. and 100% humidity overnight, they were transferred to a greenhouse at 20 ° C. to promote disease.
Seven days after the inoculation, the number of barley powdery mildew lesions per leaf was examined, and the control value (%) was calculated by the following formula.

This test was carried out in a 3-pot system for each chemical solution concentration, the average control value (%) was determined, and converted to an evaluation value of the control effect in the same manner as in Test Example 1. Further, the phytotoxicity to barley was investigated and displayed according to the same criteria as in Test Example 1.
The results are as shown in Table 10.

[0091]

(Equation 3)

[0092]

[Table 10]

Test Example 6 Cucumber downy mildew control effect test A second leaf stage seedling of a cucumber (cultivar: Sagamihanjiro) cultivated in a greenhouse in a plastic pot having a diameter of 6 cm was used in accordance with Example 5. 10 ml of each pot was sprayed with a predetermined concentration diluted solution of the wettable powder thus prepared.
On the day after the chemical treatment, the cucumber downy mildew (Pseudoperonospora) which had been formed on cucumber leaves in advance
(Cubensis: Pseudoperonosporacvensis) conidiospores with a 50 ppm aqueous solution of a spreading agent (polyoxyethylene alkyl ether) to give a spore concentration of 5 × 10.
^The number of spores was adjusted to ⁵ (pieces) / ml, and this was sprayed and inoculated on the leaves of cucumber using a spray gun. 20 ℃, humidity 1
After being kept overnight in a 00% inoculation box, they were transferred to a greenhouse at 24 ° C. to promote disease. Six days after the inoculation, the disease area ratio (%) per leaf was investigated, the average disease area ratio was calculated, and the control value (%) was calculated by the following formula.

This test was carried out in a 3-pot system for each chemical solution concentration, the average control value (%) was determined, and converted into an evaluation value by the same method as in Test Example 1. In addition, the same criteria as in Test Example 1 were used to investigate the chemical damage to cucumber. The results are shown in Table 1.
It is as shown in 1.

[0095]

[Equation 4]

[0096]

[Table 11]

Test Example 7 Tomato Late Blight Control Effect Test Prepared according to Example 5 on the 5th leaf stage seedling of tomato (cultivar: Toko K) cultivated in a greenhouse in a plastic pot having a diameter of 6 cm. A predetermined concentration of the wettable powder was diluted with 10 ml per pot using an automatic spraying device. The day after drug treatment, Phytophthora ( Phytophthora) was formed on previously sliced potato pieces.
infestans : phytophytotra infestans ) were treated with a 50 ppm aqueous solution of a spreading agent (polyoxyethylene alkyl ether) to increase the concentration of zoospores to 5 ×.
The number was adjusted to 10 ⁵ spores (pieces) / ml, and the tomato was spray-inoculated using a spray gun. After being kept in an inoculation box at 20 ° C. and 100% humidity overnight, it was transferred to a greenhouse at 24 ° C. to promote disease onset. Four days after the inoculation, the diseased area percentage (%) of the first to fourth true leaves of tomato blight was investigated, the average diseased area percentage was determined, and the control value (%) was calculated by the following formula.

This test was carried out in a 3-pot system for each chemical solution concentration, the average control value (%) was determined, and converted into an evaluation value by the same method as in Test Example 1. In addition, the same criteria as in Test Example 1 were used to investigate the chemical damage to tomatoes. The results are shown in Table 12.
It is as follows.

[0099]

(Equation 5)

[0100]

[Table 12]

Test Example 8 Cucumber Gray Mold Control Effect Test A second leaf stage seedling of a cucumber (cultivar: Sagamihanjiro) cultivated in a greenhouse in a plastic pot having a diameter of 6 cm was used in accordance with Example 5. A predetermined concentration of the wettable powder thus prepared was sprayed in an amount of 10 ml per pot using an automatic spraying device. The day after the chemical treatment, the cucumber gray mold fungus ( Botrytis c) previously cultivated in a potato decoction medium was used.
inerea : Botrytis cinerea) was inoculated by inoculation with agar-containing agar pieces. After being kept in an inoculation box at 20 ° C. and 100% humidity overnight, it was transferred to a greenhouse at 24 ° C. to promote disease onset. Inoculation 4
After the day, the lesion diameter (cm) per leaf was measured, the average lesion diameter was calculated, and the control value (%) was calculated by the following formula.

This test was carried out in a 3-pot system for each chemical solution concentration, the average control value (%) was determined, and converted into an evaluation value by the same method as in Test Example 1. In addition, the same criteria as in Test Example 1 were used to investigate the chemical damage to cucumber. The results are shown in Table 1.
3

[0103]

(Equation 6)

[0104]

[Table 13]

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification number Office reference number FI technical display location C07D 401/14 239 C07D 401/14 239 // (C07D 401/12 213: 16 239: 28) ( (C07D 401/12 213: 61 239: 28) (C07D 401/04 213: 61 239: 28) (C07D 401/04 213: 16 239: 38) (C07D 401/14 213: 16 213: 61 239: 28) (C07D 401/14 213: 16 239: 28) (72) Inventor Seiichi Kutsuma 5-9-901 Tsuzumadahigashi, Atsugi-shi, Kanagawa Prefecture (72) Chikako Ohno 501-1 Toda, Atsugi-shi, Kanagawa Prefecture Crest Univ. No. 203 (72) Inventor Yasushi Noshiro 2385 Toda, Atsugi City, Kanagawa Prefecture

Claims (3)

[Claims] 1. A general formula:(In the formula, X represents a halogen atom, and Y and Z are
Each of them may be different from each other, and an oxygen atom, a sulfur atom or
Is NR Represents a group, and A is a monoalkyl or lower alkyl group.
Represents a di-substituted C1-C6 alkylene group, n
Is an integer of 0, 1 and 2, where R Is a hydrogen source
Child, lower alkyl group, and B may be different from each other.
Hydrogen atom, lower alkyl group, lower haloalkyl group,
A lower alkoxy group or a lower alkylamino group
Or halogen atom, lower alkyl group, lower haloalkyl
Group or phenyl optionally substituted with a lower alkoxy group
Group or pyridyl group, m represents an integer of 1 to 3
You. )). 2. A general formula:(In the formula, X represents a halogen atom, and Y and Z are
Each of them may be different from each other, and an oxygen atom, a sulfur atom or
Is NR Represents a group, and A is a monoalkyl or lower alkyl group.
Represents a di-substituted C1-C6 alkylene group, n
Is an integer of 0, 1 and 2, where R Is a hydrogen source
Child, lower alkyl group, and B may be different from each other.
Hydrogen atom, lower alkyl group, lower haloalkyl group,
A lower alkoxy group or a lower alkylamino group
Or halogen atom, lower alkyl group, lower haloalkyl
Group or phenyl optionally substituted with a lower alkoxy group
Group or pyridyl group, m represents an integer of 1 to 3
You. ) As an active ingredient
A fungicide for agricultural and horticultural use, characterized in that 3. A compound of the general formula (In the formula, B may be different from each other and is a hydrogen atom, a lower alkyl group, a lower haloalkyl group, a lower alkoxy group or a lower alkylamino group, or a halogen atom, a lower alkyl group, a lower haloalkyl group or a lower alkoxy group. Represents a phenyl group or a pyridyl group which may be substituted with, and m represents an integer of 1 to 3.).