JP3109012B2 - Thiazolo [5,4-d] pyrimidine derivatives and fungicides for agricultural and horticultural use - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a thiazolo [5,4-
d] A pyrimidine derivative and an agricultural and horticultural fungicide containing the same as an active ingredient.

[0002]

2. Description of the Related Art Hitherto, as a thiazolo [5,4-d] pyrimidine derivative having a physiological activity, a compound having a hypotensive effect described in German Patent No. 2,155,963, A compound having a vasodilatory action described in Japanese Patent No. 101,518;
The compounds having anti-inflammatory activity described in French Patent 2,581,067 are known. Also,
In addition, Chemical and Pharmaceutical Bulletin (Chem. Pharm. Bull.),
Vol. 16- (4), pp. 741-55 (1968), examples of various thiazolo [5,4-d] pyrimidines having an antitumor effect or a bactericidal effect are disclosed in 62-129,282 describes an intermediate as a pharmaceutical. However, these documents all describe pharmaceutical-related physiological activities, and there is no description on the action related to pesticides.

On the other hand, in the field of agricultural and horticultural fungicides, the emergence of drug-resistant bacteria often poses a problem. For example, in the case of rice blight seedling disease, pesticides containing a mixture of methyl-1- (butylcarbamoyl) -2-benzimidazole carbamate and bis (dimethylcarbamoyl) disulfide have been most widely used as a control agent therefor. However, sufficient control effect has not been obtained due to the emergence of drug-resistant bacteria.

Further, a thiadiazolo [3,2-a] pyridimin-5-one derivative, which is similar to the thiazolo [5,4-d] pyrimidine derivative of the present invention, is disclosed in Japanese Unexamined Patent Publication No. The compounds described in JP-A-63-10706 and JP-A-63-10794 are known. This compound group has a high effect on various plant diseases, especially Komatsuna black spot, apple spot leaf rot, cucumber gray mold, rice blast, and tomato late blight, but rice has been regarded as a problem by the emergence of drug-resistant bacteria. Sufficient effects have not been obtained for falcon seedling disease.

[0005]

In the cultivation of agricultural and horticultural crops, a large number of control agents have been used against diseases of useful crops. However, they have various drawbacks, such as insufficient control effect, limited use due to the emergence of drug-resistant bacteria, phytotoxicity and contamination of plants, and strong toxicity to humans, livestock and fish. Therefore, there are many things that are not necessarily satisfactory fungicides.
Therefore, there is a strong demand for a drug that can be safely used with less of these drawbacks.

[0006]

DISCLOSURE OF THE INVENTION The present inventors have proposed thiazolo [5,4-d], whose biological activity on pesticides is unknown.
As a result of studies on pyrimidine derivatives, it has been found that the compound represented by the general formula [I] having a sulfonyl group or a sulfoxide group at the 2-position of the ring is excellent in disinfecting various plant diseases, particularly crop seeds. The present invention was completed by finding that there was none.

That is, the present invention relates to a novel compound which has not been described in the literature and has the general formula [I]

[0008]

Embedded image

Wherein X is a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a phenyl group, a haloalkyl group, an anilino group or a phenoxy group (the group may be substituted with a halogen atom, an alkyl group or an alkoxy group) ), Y represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a phenyl group, a phenoxy group or an anilino group, and R represents an alkyl group, a benzyl group, a phenyl group, an alkenyl group, a cycloalkyl group, or a halogen-substituted group. It represents an alkyl group, an alkoxycarbonylalkyl group, an alkoxyalkyl group or a phenylalkyl group, and n represents an integer of 1 or 2. A thiazolo [5,4-d] pyrimidine derivative represented by｝ and an agricultural and horticultural fungicide containing the same as an active ingredient.

Next, specific examples of the compound of the present invention are shown in Tables 1 to 7.
I will give it. The compound numbers will be referred to in the following description.

[0011]

[Table 1]

[0012]

[Table 2]

[0013]

[Table 3]

[0014]

[Table 4]

[0015]

[Table 5]

[0016]

[Table 6]

[0017]

[Table 7]

The compound [I] of the present invention is, for example, a compound represented by the general formula [I
Compound represented by I]

[0019]

Embedded image

(Wherein, X, Y and R have the same meanings as described above).

The oxidation of the compound represented by the general formula [II] can be carried out by a method usually used for oxidizing organic sulfides. Examples of oxidizing agents that can be used include hydrogen peroxide and organic peracids such as m-chloroperbenzoic acid. The oxidation reaction can be accelerated by using an acid catalyst such as acetic acid together with the oxidizing agent.

Solvents that can be used in the oxidation include, for example, halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, and chlorobenzene; fatty acids such as acetic acid and propionic acid; ketones such as acetone and methyl ethyl ketone; Examples include amides such as dimethylformamide and dimethylacetamide, hydrocarbons such as hexane, petroleum ether, and benzene, and water. The temperature at the time of oxidation is in the range of −20 ° C. to the boiling point of the solvent. When the amount of the oxidizing agent is n with respect to the compound represented by the general formula [II], it is usually performed in an equivalent amount,
When n is 2, the reaction is usually performed with 2 equivalents or more, but is not limited thereto.

The production of the compound represented by the general formula [II] used as a starting material can be largely classified into two methods: a method for producing from a pyrimidine derivative (Production A) and a method for producing from a thiazole derivative (Production B). Can be classified. The production method A further includes a case where the pyrimidine has one hydroxy group at either the 4-position or the 6-position as a production raw material (the production method A).
-1), when the pyrimidine has two hydroxy groups at the 4- and 6-positions (Production method A-2) and when it has two hydroxy groups at the 2- and 4-positions and a mercapto group at the 6-position (Production method A)
-3). Hereinafter, each production method will be described.

Production method A-1

[0025]

Embedded image

[0026]

Embedded image

In the formula, X ¹ represents a hydrogen atom, an alkyl group, a haloalkyl group, a phenyl group, a hydroxy group or a mercapto group; X ² represents a hydrogen atom, a halogen atom, an alkyl group, a haloalkyl group or a phenyl group; X ³ represents a halogen atom, an alkoxy group, a phenoxy group (the group may be substituted with a halogen atom, an alkyl group, or an alkoxy group) or an anilino group, and Y ¹ represents a hydrogen atom, an alkyl group, or a phenyl group. , U is a halogen atom,
Represents an optionally substituted benzenesulfonyloxy group,
R are as defined above, R ¹ is a lower alkyl group, R ²
Represents an alkyl group, an alkenyl group, a benzyl group, an alkoxycarbonylalkyl group, a halogen-substituted alkyl group, a cycloalkyl group, a phenylalkyl group or an alkoxyalkyl group, and R ³ represents an alkyl group, a phenyl group (the group is a halogen atom, an alkyl Or an alkoxy group). ｝

In the above reaction, compound [VI] is synthesized, for example, from Journal of the American Chemical Society (J. Am. Chem. Soc.), No. 41
, P. 783 (1919), by nitrating compound [III] with fuming nitric acid and, if necessary, mixed acid of concentrated nitric acid and concentrated sulfuric acid.

X ^{1 of the} compound [VI] is an alkyl group,
When Y ¹ is a hydrogen atom, it represents a phenyl group or a haloalkyl group, and when Y ¹ is a hydrogen atom, for example, J. Heterocyclic.C.
hem. ), Vol. 22, p. 337 (1985), and the compound [IV] and the compound [V].
It can also be produced by a cyclization reaction with

Next, for example, the Journal of the American Chemical Society (J. Am. Che
m. Soc. ), Page 1565 (1951), compound [VI] is oxychlorinated in the presence of a dehydrohalogenating agent such as N, N-dimethylaniline or N, N-diethylaniline. Compound [VII] can be produced by chlorination with phosphorus or the like. At this time, when the 2-position is a hydroxy group or a mercapto group, the 2-position is simultaneously chlorinated.

The compound [VII] thus obtained
For example, Chemical and Pharmaceutical Bulletin (Chem. Pharm. Bull.),
Vol. 6, p. 343 (1958), the nitro group is reduced with iron or the like in the presence of an acid such as acetic acid or hydrochloric acid to produce compound [VIII]. . Compound [X] can be produced by reacting compound [VIII] with carbon disulfide in the presence of potassium alkyl xanthate or potassium hydroxide in an alcohol solvent.

On the other hand, for example, Chemical and Pharmaceutical Bulletin (Chem. Pharm.
Bull. ), Vol. 6, p. 343 (1958), and compound [IX] can be produced from compound [VIII] and potassium or sodium hydrosulfide.

Further, this compound [IX] can be prepared by, for example, using Chemical and Pharmaceutical Bulletin (Chem. Pharm. Bull.), Vol.
According to the method described on page 41 (1968),
Compound (X) is reacted with carbon disulfide in the presence of potassium alkyl xanthate or an alcohol solvent in the presence of potassium hydroxide to give compound (X), and compound (X) is reacted with compound (XIII) in the presence of a base to give compound (XV ] Can be manufactured.

Further, the compound [IX] is reacted with phosgene or trichloromethyl chloroformate to give the compound [XI]
Can be manufactured. Compound [XI] is converted to N, N
-Compound (XII) by chlorination with phosphorus oxychloride or the like in the presence of a dehydrohalogenating agent such as -dimethylaniline or N, N-diethylaniline, and compound (XII) in the presence of a base in the presence of a compound ( XIV] to produce compound [XV].

When the substituent X ² is a halogen atom, the compound [XV] can be halogen-exchanged by using potassium fluoride or the like. Further, the compound (XV) is reacted with formanilide in the presence of a base such as an alkali metal or an alkali metal hydride to give a compound (XVII),
Next, the compound [XVII] in which X ³ is an anilino group can be produced by isolating or hydrolyzing the compound [XVII] with an acid or alkali without isolation.

On the other hand, when the substituent X ² of the compound [X] is a halogen atom, the compound [X] is reacted with an alcohol or phenol in the presence of a base to give the compound [XVI]
And then reacting compound [XVI] with compound [XIII] in the presence of a base to produce compound [XVIII] in which substituent X ³ is an alkoxy group or a phenoxy group.

Production method A-2

[0038]

Embedded image

[0039]

Embedded image

(Where X ⁴ is a hydrogen atom, an alkyl group, a haloalkyl group, a phenyl group, Y ² is a chlorine atom, an alkoxy group, a phenoxy group, a methyl group, Y ³ is a hydrogen atom, OR ³
Group, methyl group, Y ⁴ is OR ³ group, anilino group, Y ⁵ is hydrogen atom, OR ³ group, methyl group, anilino group, R, R ² , R ³
And U have the same meaning as described above. )

Most of the respective reactions shown in the reaction formulas can be carried out in the same manner as in the production method A-1. Hereinafter, a different reaction from the production method A-1 will be described.

Compound [XXII] can be produced by reacting compound [XXI] with an alcohol or phenol in the presence of a base. On the other hand, the compound [XXI] is reacted with a malonic ester in the presence of a base and then hydrolyzed with an acid to produce a compound [XXIII], and the compound [XXIII] is converted to N, N-dimethylaniline or N ,
Compound [XXIV] is produced by chlorination with phosphorus oxychloride or the like in the presence of a dehydrohalogenating agent such as N-diethylaniline, and then Y ^{2 is} obtained by reducing the nitro group of compound [XXIV]. Is a methyl group (XXV)
Can be manufactured.

When Y ² of compound [XXVI] is a chlorine atom,
Compound [XXVII] is produced by reduction, and then compound [XXVII] is cyclized to produce compound [XXVIII] wherein Y ³ is a hydrogen atom. Compound (XX
XII] is a novel compound. When Y ⁴ is an alkoxy group or a phenoxy group, it can be produced by reacting compound [XXX] with an alcohol or phenol in the presence of a base. When Y ⁴ is an anilino group, the compound [XXX] is reacted with formanilide in the presence of a base such as an alkali metal or an alkali metal hydride to give a compound [XXXI], and then the compound [XXXI] is isolated or It can be produced by hydrolysis with an acid or alkali without isolation.

Production method A-3

[0045]

Embedded image

(In the formula, U and R ² have the same meanings as described above.)

Justus Liebig Annalen
Der Hemy (Liebigs Ann. Che)
m. ), Vol. 288, p. 159 (1895), and the compound [XXXVII] from the known compound [XXXIV].
Is manufactured, for example, by Chemical and Pharmaceutical Bulletin (Chem. Pharm. Bul).
l. ), Vol. 16, p. 750 (1968).

Manufacturing method B

[0049]

Embedded image

(Wherein Z ¹ is an alkoxycarbonyl group,
A carbamoyl group, X ⁵ is a hydrogen atom, an alkyl group, R ¹ , R
² , R ³ , Y ⁴ and U have the same meaning as described above. )

The Journal of the Chemical Society (J. Chem. Soc.), P. 1598 (19)
47 years) or Journal of the Chemical
A known compound [XXXVII] described in Society (J. Chem. Soc.), P. 1440 (1949).
The compound [XXXIX] can be produced by reacting the compound [I] with the compound [XIII] in the presence of a base.

Compound [XXXIX] was converted from Indian Journal of Chemistry (Indian J. Ch.)
em. ), SECTION B, 18B, p. 30 (19
Compound [XLII] according to the method described in
I] and [XLIV]. That is, a compound [XXXIX] is reacted with a compound [XLI] or formamide, and a compound [XLIII] wherein X ⁵ is a hydrogen atom or an alkyl group.
To manufacture. Further, the compound [XXXIX] is reacted with the compound [XL] to produce a compound [XLII] as an intermediate, and then the compound [XLII] is condensed and cyclized with polyphosphoric acid, sulfuric acid, or the like to form a compound in which X ⁵ is a phenyl group. [XLIII] can be produced.

Compound [XLIII] is chlorinated with phosphorus oxychloride or the like in the presence or absence of a dehydrohalogenating agent such as N, N-dimethylaniline or N, N-diethylaniline to give compound [XLIII]. XLIV] can be produced. Compound [XLIV] wherein Y ⁴ is R ³ O can be produced by reacting compound [XLIV] with an alcohol or phenol in the presence of a base. Y ⁴
Is an anilino group (XLVI), the compound (XLIV) is reacted with formanilide in the presence of a base such as an alkali metal or an alkali metal hydride to give a compound (XLV), and the compound (XLV) is isolated or isolated. It can be produced by hydrolysis with an acid or alkali without separation.

[0054]

EXAMPLES The production method, formulation method and effects of the present invention will now be described specifically with reference to examples.

Production Example 1 5-chloro-2-ethylsulfonylthiazolo [5,4-
d] Preparation of pyrimidine (Compound No. 4) 47 g of 5-chloro-2-ethylthiothiazolo [5,4-d] pyrimidine, sodium tungstate dihydrate 2.8
g was dissolved in 250 ml of acetic acid, and 67 g of 31% aqueous hydrogen peroxide was added dropwise thereto. The reaction solution was stirred under reflux for 20 minutes, and the reaction solution was poured into 600 ml of water. The precipitate was collected by filtration, washed with an aqueous solution of sodium hydrogen sulfite and water, and recrystallized with ethanol to give 5-chloro-ethylsulfonylthiazolo [5,4.
-D] Pyrimidine 39 g was obtained. Melting point 106-109
° C, yield 72%.

Production Example 2 Production of 5-chloro-2-isopentylsulfinylthiazolo [5,4-d] pyrimidine (Compound No. 17) 5-chloro-2-isopentylthiothiazolo [5,4-
d) Pyrimidine (2.1 g) was dissolved in dichloromethane (50 ml), m-chloroperbenzoic acid (3.8 g) was added thereto, and the mixture was stirred at room temperature for 2 hours. The reaction solution was washed with a 5% aqueous potassium carbonate solution and water, and the organic solvent layer was dried over anhydrous magnesium sulfate. After the solvent was distilled off, the residue was purified by silica gel column chromatography to give 1.4 g of 5-chloro-2-isopentylsulfinylthiazolo [5,4-d] pyrimidine.
I got 110-116 ° C, 64% yield.

Production Example 3 Production of 5-chloro-2-sec-butylsulfonylthiazolo [5,4-d] pyrimidine (Compound No. 12) 5-chloro-2-sec-butylthiothiazolo [5,4
-D] Pyrimidine 1.4 g, m-chloroperbenzoic acid 2.7 g
Was dissolved in 40 ml of dichloromethane and stirred at room temperature for 10 hours. The reaction solution was washed with a 5% aqueous potassium carbonate solution and water,
The organic solvent layer was dried with anhydrous magnesium sulfate. After evaporating the solvent, the residue was recrystallized from ethanol to give 5-chloro-
2-sec-butylsulfonylthiazolopyrimidine 1.
2 g were obtained. 83-89 ° C, 75% yield.

Production Example 4 2-ethylsulfonyl-5-methoxythiazolo [5,4
Preparation of -d] pyrimidine (Compound No. 36) 2-ethylthio-5-methoxythiazolo [5,4-d]
Pyrimidine (3.0 g) and m-chloroperbenzoic acid (6.2 g) were dissolved in dichloromethane (100 ml) and stirred at room temperature for 2 hours.
The reaction solution was washed with a 5% aqueous potassium carbonate solution and water, and the organic solvent layer was dried over anhydrous magnesium sulfate. After evaporating the solvent, the residue was recrystallized from ethanol to obtain 2.5 g of 2-ethylsulfonyl-5-methoxythiazolo [5,4-d] pyrimidine. 122-124 ° C, 73% yield.

Production Example 5 2-ethylsulfonyl-7-methoxythiazolo [5,4
Preparation of -d] pyrimidine (Compound No. 48) 2-ethylthio-7-methoxythiazolo [5,4-d]
0.7 g of pyrimidine and 1.5 g of m-chloroperbenzoic acid were dissolved in 60 ml of dichloromethane and stirred at room temperature for 2 hours. The reaction solution was washed with a 5% aqueous potassium carbonate solution and water, and the organic solvent layer was dried over anhydrous magnesium sulfate. After evaporating the solvent, the residue was recrystallized from ethanol to give 2-ethylsulfonyl-
0.7 g of 7-methoxythiazolo [5,4-d] pyrimidine
I got 114-117 ° C, 88% yield.

Preparation Example 6 Preparation of 2-benzylsulfonyl-5,7-dimethylthiazolo [5,4-d] pyrimidine (Compound No. 57) 2-benzylthio-5,7-dimethylthiazolo [5,4-
d] Pyrimidine (0.9 g) and m-chloroperbenzoic acid (1.6 g) were dissolved in dichloromethane (60 ml) and stirred at room temperature for 4 hours. The reaction solution was washed with a 5% aqueous potassium carbonate solution and water, and the organic solvent layer was dried over anhydrous magnesium sulfate. After evaporating the solvent, the residue was purified by silica gel column chromatography to obtain 0.7 g of 2-benzylsulfonyl-5,7-dimethylthiazolo [5,4-d] pyrimidine. 167-170 ° C, 70% yield.

The fungicide for agricultural and horticultural use of the present invention comprises thiazolo [5,
4-d] pyrimidine derivative as an active ingredient. When the compound of the present invention is used as an agricultural and horticultural fungicide, the active ingredient can be used in an appropriate dosage form according to the purpose. Usually, the active ingredient is diluted with an inert liquid or solid carrier, and if necessary, a surfactant and the like can be added to the active ingredient to be used in the form of powders, wettable powders, emulsions, granules and the like.

Examples of suitable carriers include solid carriers such as talc, bentonite, clay, kaolin, diatomaceous earth, white carbon, vermiculite, slaked lime, silica sand, ammonium sulfate, and urea; and liquid carriers such as isopropyl alcohol, xylene, cyclohexanone, and methylnaphthalene. And the like. As the surfactant and dispersant, for example, dinaphthyl methanesulfonate, alcohol sulfate, alkylaryl sulfonate, lignin sulfonate,
Polyoxyethylene glycol ether, polyoxyethylene alkyl aryl ether, polyoxyethylene sorbitan monoalkylate and the like can be mentioned. Examples of the auxiliary include carboxymethyl cellulose.
These preparations are diluted to an appropriate concentration and sprayed or applied directly.

The fungicide for agricultural and horticultural use of the present invention can be used by dipping seed, seed dressing, foliage application, soil application or water application. The mixing ratio of the active ingredient is appropriately selected according to need, but in the case of powder and granules, it is 0.1 to 20.
% (Weight), or 5 to 80 when used as an emulsion or wettable powder
% (Weight) is appropriate.

The application rate of the fungicide for agricultural and horticultural use of the present invention varies depending on the kind of the compound to be used, the target disease, the tendency to occur, the degree of damage, the environmental conditions, the dosage form to be used, and the like. For example, when used as such as powders and granules, the active ingredient may be appropriately selected from the range of 0.1 g to 5 kg, preferably 1 g to 1 kg per 10 ares. When used in liquid form such as emulsions and wettable powders, 0.1 ppm
-10,000 ppm, preferably 10-3,000 ppm
It is good to select appropriately from the range.

The compounds according to the invention can, depending on the application forms described above, be used for algal fungi (Oomycetes), ascomycetes (Ascomycetes),
Deuteromycetes and Basidiom fungi
ycetes). Next, specific bacterial names are given as non-limiting examples. Pseudoperonospora (Pseudoperonospora) genus, for example, downy mildew (Pseudoperonospora cubensis), spheroteca (Spha)
erotheca), for example, powdery mildew (Sphaerotheca f
uliginea), the genus Venturia, for example, scab fungus (Venturia inaequalis), Pyricularia (Pyr)
icularia), for example, blast fungus (Pyricularia oryz)
ae), the genus Gibberella, for example, the germ-pathogenic fungus (Gibberella fujikuroi), Botrytis (Botrytis)
Genus, for example, Botrytis cinerea, Alternaria, for example, Alternaria brassicicola, Rhizoctonia (Rhizo)
ctonia), for example, Rhizoctonia solan
i), genus Puccinia, for example, rust fungus (P
uccinia recondita).

Further, the compound of the present invention may be mixed with an insecticide, other fungicides, herbicides, plant growth regulators, fertilizers and the like, if necessary. Next, the formulation method will be specifically described with reference to typical formulation examples of the agricultural and horticultural fungicides of the present invention. In the following description, “%” indicates weight percentage.

Formulation Example 1 Dust 2% of compound (8), 5% of diatomaceous earth and 93% of clay were uniformly mixed and pulverized to give a dust.

Formulation Example 2 Wettable powder 50% of compound (4), 45% of diatomaceous earth, 2% of sodium dinaphthylmethanedisulfonate and 3% of sodium ligninsulfonate were uniformly mixed and pulverized to obtain a wettable powder.

Formulation Example 3 Emulsion 30% of compound (12), 20% of cyclohexanone, 11% of polyoxyethylene alkylaryl ether, 4% of calcium alkylbenzenesulfonate and 35% of methylnaphthalene were uniformly dissolved to form an emulsion.

Formulation Example 4 Granules Compound (94) 5%, lauryl alcohol sulfate sodium salt 2%, lignin sulfonate sodium 5
%, Carboxymethylcellulose 2% and clay 86%
Is uniformly mixed and pulverized. 20% of water was added to the mixture, and the mixture was kneaded, processed into granules of 14 to 32 mesh using an extrusion granulator, and then dried to obtain granules.

[0071]

INDUSTRIAL APPLICABILITY The fungicide for agricultural and horticultural use of the present invention has a high control effect on rice blight seedling disease, cucumber gray mold and rice blast disease, and is clearly superior to known compounds. have.

Next, the effects of the fungicide for agricultural and horticultural use of the present invention will be described in detail with reference to test examples. Test Example 1 Rice Blight Seedling Disease Effect Test A wettable powder prepared according to Formulation Example 2 was used, and the active ingredient concentration was 3
15 g of rice seeds (variety: Shizama) with rice baka seedling disease was added to 50 ml of a drug solution diluted with water to 0 ppm at 20 ° C.
Dipped for 4 hours. After air-drying, the solution was added to 50 ml
Soaked for 8 hours. Next, after germinating at 32 ° C. for 20 hours, the seeds were sown in a rice nursery box and placed in a seedling incubator at 30 ° C. for 2 days. After that, the seedlings were raised in a greenhouse, and on the 20th day after sowing, the number of diseased seedlings of rice blight seedling disease was investigated.
Further, the control value was calculated according to Equation 2. The results are shown in Table 8. The following two compounds were similarly formulated as comparative drugs and tested.

Comparative drug A: JP-A-62-129,282
Compound described in the specification

[0074]

Embedded image

Comparative drug B: Compound described in JP-A-63-10,794.

[0076]

Embedded image

[0077]

(Equation 1)

[0078]

(Equation 2)

[0079]

[Table 8]

Test Example 2 Control effect test on rice seeds affected by benzimidazole-based drug resistant rice baka seedling disease Paddy rice seeds (variety: Tanginboshi), which were infected with rice bacillus seedling-resistant fungi resistant to benzimidazole-based drug, were tested. The test was performed in exactly the same manner as described in Test Example 1. The results are shown in Table 9. In addition, as a comparative drug, methyl-1-
(Butylcarbamoyl) -2-benzimidazole carbamate and bis (dimethylcarbamoyl) disulfide (20% + 20%) mixed water dispersant having an active ingredient concentration of 10
The sample was diluted to be 00 ppm + 1000 ppm for the test.

[0081]

[Table 9]

Test Example 3 Test for Preventive Effect on Cucumber Gray Mold 12 cucumber seeds (variety: Sagami Hanshiro) were sowed in each of a 9 cm × 9 cm polyvinyl chloride pot and grown in a greenhouse for 7 days. The wettable powder prepared according to Formulation Example 2 was diluted with the active ingredient to 500 ppm in water to the cucumber seedlings in which the cotyledons had developed, and 10 ml per pot was sprayed. After air-drying, a mycelia trituration solution of cucumber gray mold fungus (Botrytis cinerea) was sprayed and inoculated, and immediately placed in a humid room at 22 ° C. Three days after the inoculation, the disease severity of the whole pot was investigated and evaluated according to the following criteria. The results are shown in Table 10.

Disease index 0: No disease was found Disease index 1: Disease area less than 25% Disease index 2: Disease area of 25% or more and less than 50% Disease index 3: Disease area of 50% or more and less than 75% Disease index 4 : Affected area of 75% or more

Evaluation A: Onset index 0 Evaluation B: Onset index 1 Evaluation C: Onset index 2 Evaluation D: Onset index 3 and 4

[0085]

[Table 10]

Test Example 4 Rice Blast Preventive Effect Test About 15 rice seeds (variety: Asahi Aichi) were sowed in a clay pot having a diameter of 7 cm and cultivated in a greenhouse for 2 to 3 weeks. A wettable powder prepared according to Formulation Example 2 was diluted with water so that the active ingredient concentration was 500 ppm in a rice seedling in which the fourth leaf was completely developed,
10 ml was sprayed per pot. After air drying, the rice blast fungus (Py
conidia suspension was spray-inoculated and immediately placed in a moist chamber at 25 ° C for 24 hours. Thereafter, the cells were transferred into a greenhouse, and 5 days after the inoculation, the number of lesions on the fourth leaf was counted, and the control value was calculated according to Equation 3. The results are shown in Table 11.

[0087]

(Equation 3)

Evaluation A: Control value 100% Evaluation B: Control value 80% or more and less than 100% Evaluation C: Control value 50% or more and less than 80% Evaluation D: Control value 50% or less

[0089]

[Table 11]

[0090]

──────────────────────────────────────────────────続 き Continuation of the front page (72) Inventor Shigeru Hayashi 1-970, Shinno, Hamaoka-machi, Ogasa-gun, Shizuoka Prefecture Examiner Shinobu Tanio (56) References JP-A-62-129282 (JP, A) JP-A-63- 10794 (JP, A) (58) Field surveyed (Int. Cl. ⁷ , DB name) C07D 513/04 351 A01N 43/90 104 CA (STN) REGISTRY (STN)

Claims (2)

(57) [Claims] 1. A compound of the general formula In the formula, X represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a phenyl group, a haloalkyl group, an anilino group, or a phenoxy group (the group may be substituted with a halogen atom, an alkyl group, or an alkoxy group). Show, Y
Represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a phenyl group, a phenoxy group or an anilino group, R represents an alkyl group, a benzyl group, a phenyl group, an alkenyl group, a cycloalkyl group, a halogen-substituted alkyl group,
It represents an alkoxycarbonylalkyl group, an alkoxyalkyl group or a phenylalkyl group, and n represents an integer of 1 or 2. A thiazolo [5,4-d] pyrimidine derivative represented by｝. 2. The thiazolo [5,4-d] according to claim 1.
An agricultural and horticultural fungicide containing a pyrimidine derivative as an active ingredient.