JP2639049B2 - Pyridylpyrimidine derivatives and fungicides for agricultural and horticultural use containing the same as active ingredients - Google Patents

Description

The present invention relates to a novel pyridylpyrimidine derivative and a fungicide for agricultural and horticultural use containing the same as an active ingredient.

<Problems to be Solved by Conventional Techniques and Inventions> In recent years, the safety of pesticides has become a problem from the viewpoints of environmental pollution, crop residues, and the like. Therefore, development of a novel pesticide that has low toxicity and does not accumulate in animals and plants or in soil is desired. Although many studies have been made as means for this purpose, in the case of fungicides, for example, the development of a highly active compound or a broad spectrum compound is considered to be an effective means.

<Means for Solving the Problems> The present inventors have conducted intensive studies to find a fungicide having high activity and a broad spectrum, and as a result, the general formula Wherein R ₁ represents a lower haloalkoxy group, a lower alkenyloxy group or a lower alkynyloxy group, R ₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a lower haloalkyl group or a halogen atom, and R ₃ represents Represents a hydrogen atom or a lower alkyl group, and R ₄ represents a lower alkyl group. The pyridylpyrimidine derivative represented by the formula (hereinafter, referred to as the compound of the present invention) has excellent preventive efficacy and treatment against various diseases in a wide range of fields such as rice, barley, and fruits and vegetables. The present invention has been found to exhibit efficacy and also exhibit sufficient control efficacy against bacteria resistant to various existing fungicides, leading to the present invention.

Examples of the compound of the present invention include the following compounds, but are not necessarily limited to these compounds.

4-methyl-2- (6- (o-2,2,2-trifluoroethoxyphenyl) -2-pyridyl) pyrimidine 4-methyl-2- (6- (o-1,1,2,2-tetra Fluoroethoxyphenyl) -2-pyridyl) pyrimidine 2- (6-o-difluoromethoxyphenyl-2-pyridyl) -4-methylpyrimidine 4-methyl-2- (6-o-trifluoromethoxyphenyl) -2-pyridyl ) Pyrimidine 2- (6-o-difluoromethoxyphenyl-2-pyridyl) -4-ethylpyrimidine 2- (4-methyl-6- (o-2,2,2-trifluoroethoxyphenyl) -2-pyridyl) -4-Methylpyrimidine 2- (4-methyl-6- (o-1,1,2,2-tetrafluoroethoxyphenyl) -2-pyridyl) -4-methylpyrimidine 2- (6-o-difluoromethoxy) Nyl-4-methyl-2-pyridyl) -4-methylpyrimidine 2- (4-methyl-6-trifluoromethoxyphenyl-2-pyridyl) -4-methylpyrimidine 2- (5-methyl-6- (o- 2,2,2-trifluoroethoxyphenyl) -2-pyridyl) -4-methylpyrimidine 2- (5-methyl-6- (o-1,1,2,2-tetrafluoroethoxyphenyl) -2-pyridyl ) -4-Methylpyrimidine 2- (6-o-difluoromethoxyphenyl-5-methyl-2-pyridyl) -4-methylpyrimidine 2- (5-methyl-6-o-trifluoromethoxyphenyl-2-pyridyl) 4-methylpyrimidine 4-methyl-2- (6- (p-1,1,2,2-tetrafluoroethoxyphenyl) -2-pyridyl) pyrimidine 2- (6-p-difluoromethoxyphenyl -2-pyridyl) -4-methylpyrimidine 2- (6-m-difluoromethoxyphenyl-2-pyridyl) -4-methylpyrimidine 2- (6- (o-methyl-p-1,1,2,2-) Tetrafluoroethoxyphenyl) -2-pyridyl) -4-methylpyrimidine 2- (6- (o-chloro-p-1,1,2,2-tetrafluoroethoxyphenyl) -2-pyridyl) -4-methylpyrimidine 2- (6- (o-methoxy-p-1,1,2,2-tetrafluoroethoxyphenyl) -2-pyridyl) -4-methylpyrimidine 2- (6- (o-trifluoromethyl-p-1 , 1,2,2
-Tetrafluoroethoxyphenyl) -2-pyridyl)
-4-Methylpyrimidine 2- (6- (p-methyl-o-1,1,2,2-tetrafluoroethoxyphenyl) -2-pyridyl) -4-methylpyrimidine 2- (6- (p-methyl- o-trifluoromethoxyphenyl) -2-pyridyl-4-methylpyrimidine 2- (6- (p-chloro-o-1,1,2,2-tetrafluoroethoxyphenyl) -2-pyridyl) -4-methyl Pyrimidine 2- (6- (p-chloro-o-difluoromethoxyphenyl) -2-pyridyl) -4-methylpyrimidine 2- (6- (p-fluoro-o-1,1,2,2-tetrafluoroethoxy) Phenyl) -2-pyridyl) -4-methylpyrimidine 2- (6- (o-fluoro-p-1,1,2,2, tetrafluoroethoxyphenyl) -2-pyridyl) -4-methylpyrimidine 2- ( 6- (p-methyl-o-1,1,1 2,2-tetrafluoromethoxyphenyl) -4-methyl-2-pyridyl)
-4-methylpyrimidine 2- (6- (p-methyl-o-2,2,2-trifluoroethoxyphenyl) -2-pyridyl) -4-methylpyrimidine 2- (6- (m-methyl-p- 1,1,2,2-tetrafluoroethoxyphenyl) -2-pyridyl) -4-methylpyrimidine 4-methyl-2- (6-o-trichloromethoxyphenyl-2-pyridyl) pyrimidine 4-methyl-2- ( 6-o-propargyloxyphenyl-2-pyridyl) pyrimidine 2- (6-o-allyloxyphenyl-2-pyridyl) -4-methylpyrimidine or their hydrochlorides, hydrobromides, nitrates and the like. .

Plant diseases that can be controlled by the compound of the present invention include:
Rice blast (Pyricularia oryzae), sesame leaf blight (Cochliobolus miyabeanus), Rhizoctonia s
olani), wheat powdery mildew (Erysphe graminis fs)
p.hordei, Egfsp.tritici), Leaf spot disease (Pyrenophora g
raminea), net spot disease (Pyrenophora teres), red snow rot (Fusarium nivale), rust (Puccinia striiformis,
P.graminis, P.recOndita, P.hordei), Eye spot disease (Pseudoc)
ercosporella herpotrichoides, scald disease (RhynchOspo)
rium secalis), leaf blight (Septoria tritici), blight (Leptosphaeria nodorum), citrus black spot (Diapo
rthe citri), scab (Elsinoe fawcetti), apple powdery mildew (Podosphaera leucotricha), spot leaf rot (Alternaria mali), scab (Venturia inaequali)
s), pear scab (Venturia nashicola), black spot (A
lternaria kikuchianc), peach rot disease (Sclerotiniac)
inerea), grape scab (Elsinoe ampelina), late rot (Glomorella cingulata), powdery mildew (Uncinula)
necator), anthracnose of cucumber (Colletotrichum lagenar)
ium), powdery mildew (Sphaerotheca fuliginea), tomato ring blight (Alternaria solani), plague (Phytophthor)
a infestans), eggplant brown spot (Phomopsis vexans),
Black spot (Alternaria japonica), white spot (Cercosporella brassicae), and green onion rust (Puc) on cruciferous vegetables
cinia allii), soybean purpura (Cercospora kikuchi)
i), black rot (Elsinoe glycines), bean anthracnose (Colletotrichum lindemuthianum), peanut black rot (Mycosphaerella personatum), brown spot (Cerco)
spora arachidicola), pea powdery mildew (Erysip)
he pisi), potato summer blight (Alternaria solan)
i), brown spot of sugar beet (Cercospora beticola), rose scab (Diplocarpon rosae), powdery mildew (Sphaero
theca pannosa), gray mold on various crops (Botrytis)
cinerea) and sclerotium disease (Sclerotinia sclerotiorum).

When the compound of the present invention is used as an active ingredient of an agricultural and horticultural fungicide, it may be used as it is without adding any other components, but usually, a solid carrier, a liquid carrier, a surfactant and other auxiliary substances for pharmaceutical preparations. Mix, emulsion, wettable powder, suspension,
Formulated into granules, powders, liquids, etc. for use.

These preparations contain the compound of the present invention as an active ingredient in a weight ratio of 0.1 to 99%, preferably 0.2 to 95%.

As a solid carrier, fine powders such as kaolin clay, attapulgite clay, bentonite, acid clay, pyrophyllite, talc, diatomaceous earth, decomposed stone, corn cob powder, walnut shell powder, urea, ammonium sulfate, synthetic hydrous silicon oxide, etc. Alternatively, there is a granular substance, and the liquid carrier includes aromatic hydrocarbons such as xylene and methylnaphthalene, alcohols such as isopropanol, ethylene glycol and cellosolve, ketones such as acetone, cyclohexanone and isophorone, soybean oil, and cottonseed oil. Vegetable oil, dimethyl sulfoxide, acetonitrile, water and the like can be mentioned.

Surfactants used for emulsification, dispersion, wet spreading, etc. include alkyl sulfates, alkyl (aryl) sulfonates, dialkyl sulfosuccinates, polyoxyethylene alkyl aryl ether phosphates, and naphthalene sulfones. Examples include anionic surfactants such as acid formalin condensates, and nonionic surfactants such as polyoxyethylene alkyl ethers, polyoxyethylene polyoxypropylene block copolymers, sorbitan fatty acid esters, and polyoxyethylene sorbitan fatty acid esters. Pharmaceutical adjuvants include lignin sulfonate, alginate, polyvinyl alcohol, gum arabic, CMC (carboxymethylcellulose), PAP
(Acidic isopropyl phosphate).

These preparations may be used as they are, or diluted with water and sprayed on foliage, treated with seeds, powdered into soil, powdered and mixed, or applied to soil. Also, by using it mixed with other agricultural and horticultural fungicides,
It can also be expected to increase the control effect. Further, it can be used in combination with an insecticide, an acaricide, a nematicide, a herbicide, a plant growth regulator, a fertilizer, a soil conditioner and the like.

When the compound of the present invention is used as an active ingredient of an agricultural and horticultural fungicide, the treatment amount varies depending on weather conditions, preparation form, treatment time, method, place, target disease, target crop, etc., but is usually 0.5 per 1 are. ~ 200g, preferably 1-1
When the emulsion, wettable powder, suspending agent and the like are diluted with water for application, the application concentration is 0.0005 to 0.5%, preferably
0.001 to 0.2%, and granules, dusts, etc. are applied without dilution.

 The method for producing the compound of the present invention will be described below.

Wherein, R _'2 represents a hydrogen atom, a lower alkyl group, a lower alkoxy group or a lower haloalkyl group, R ₃ and
R ₄ has the same meaning as described above, and R ′ ₁ represents a 2,2,2-trifluoroethoxy group, a propargyloxy group, or the like;
X represents a halogen atom. In the production method A, of the compounds of the present invention, the compound represented by the general formula [IV] can be produced by an Ullmann reaction between the halobenzene derivative [II] and the alcohol [III].

Wherein R ₂ , R ₃ and R ₄ represent the same meaning as described above,
R ″ ₁ represents a difluoromethoxy group, an allyloxy group, a propargyloxy group, a 1,1,2,2-tetrafluoroethoxy group, etc.] In the production method B, a phenol derivative [V] is reacted with a halide [VI]. The compound represented by the general formula [VIII] among the compounds of the present invention can be produced by producing an ether bond by the addition or by an addition reaction between the phenol derivative [V] and the unsaturated compound [VII].

[Wherein, R ₁ , R ₂ , R ₃ and R ₄ have the same meanings as described above, R ₅ and R ₆ each represent a lower alkyl group, and M represents an alkali metal atom. In the production method C, the cyanopyridine derivative [IX] is reacted with the alkali metal compound [X] to give the imidate [XI].
And reacting it with an ammonium salt to obtain an amidine derivative [XII]. Further, a β-oxoacetal derivative [XIII] is reacted with this in the presence of a base to effect cyclization, whereby the compound of the present invention can be obtained.

<Effects of the Invention> The compound of the present invention has excellent effects on plant diseases caused by various plant pathogens, and thus can be used for various uses as an active ingredient of an agricultural and horticultural fungicide.

<Examples> Hereinafter, the present invention will be described in more detail with reference to Production Examples, Formulation Examples, and Test Examples, but the present invention is not limited to only these Examples.

 First, a production example will be described.

Production Example 1 (Compound (1)) 10.7 g of 2,2,2-trifluoroethanol and 14.7 g of anhydrous potassium carbonate were added to 100 ml of DMF and stirred at room temperature for 30 minutes.

To this was added 3 g of 2- (6-o-chlorophenyl-2-pyridyl) -4-methylpyrimidine and 0.5 g of cuprous chloride, and the mixture was heated under reflux for 3 hours.

After cooling, 200 ml of water was added to the reaction solution, and the insolubles were removed using celite. The liquid was extracted by adding 500 ml of ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was treated with silica gel column chromatography (eluent: ethyl acetate) to give 4
2.1 g of -methyl (6- (o-2,2,2-trifluoroethoxyphenyl) -2-pyridyl) pyrimidine were obtained.

mp 111.0 ° C PMR (CDCl ₃ ) δ ppm 2.60 (s, 3H, -CH ₃ ) 4.37 (δ, 2H, -CH ₂ CF ₃ , J = 7.8 Hz) 8.67 (d, 1H, pyrimidine-H ⁶ , J = 4.8 Hz) Production Example 2 (Compound (3)) I) 7.67 g of benzyl alcohol and 7.36 g of anhydrous potassium carbonate
Was added to 100 ml of DMF and stirred at room temperature for 30 minutes.

To this were added 10 g of 2- (6-o-chlorophenyl-2-pyridyl) -4-methylpyrimidine and 1.0 g of cuprous chloride, and the mixture was heated under reflux for 3 hours.

After allowing to cool, 200 ml of water was added to the reaction solution, and the insoluble matter was removed using celite. The liquid was extracted by adding 500 ml of ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate.
It was concentrated under reduced pressure. The obtained residue is subjected to silica gel column chromatography (eluent; hexane: ethyl acetate = 3: 1 (v
/ v)) to give 2.3 g of 2- (6-o-benzyloxyphenyl-2-pyridyl) -4-methylpyrimidine.

mp 112.0 ° C PMR (CDCl ₃ ) δ ppm 2.63 (s, 3H, —CH ₃ ) 5.14 (s, 2H, —O CH ₂ Ph) 8.77 (d, 1H, pyrimidine-H ⁶ , J = 4.8 Hz) II) I 2) 2- (6-o-benzyloxyphenyl-2-pyridyl) -4-methylpyrimidine obtained in the above) was dissolved in 50 ml of toluene and 30 ml of ethanol, and 0.4 g of anhydrous potassium carbonate was dissolved in 20 ml of water. And 0.2 g of 5% palladium-carbon.

The mixture was stirred vigorously and contacted with hydrogen at normal pressure for 1 hour. After removing the catalyst using celite, 100 ml of ethyl acetate was added for extraction. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 1.4 g of 2- (6-o-hydroxyphenyl-2-pyridyl) -4-methylpyrimidine.

mp 113.1 ° C PMR (CDCl ₃ ) δ ppm 2.57 (s, 3H, -CH ₃ ) 8.66 (d, 1H, pyrimidine-H ⁶ , J = 4.8 Hz) III) 2- (6-o-) obtained from II) 1 g of (hydroxyphenyl-2-pyridyl) -4-methylpyrimidine and 0.9 g of sodium hydroxide were dissolved in 10 ml of dioxane and 10 ml of water. This solution was heated to 60 ° C., and Daiflon-2.2 (CF ₂ Cl
H) Gas was passed for 1 hour.

The reaction solution was extracted by adding 50 ml of water and 100 ml of ethyl acetate,
The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure.

The obtained residue is treated with silica gel column chromatography (eluent; hexane: ethyl acetate = 3: 1 (v / v)) to give 2- (6-o-difluoromethoxyphenyl-2-pyridyl) -4-methylpyrimidine. 0.45g was obtained.

_{mp 143.1 ℃ PMR (CDCl 3)} δppm 2.64 (s, 3H, - CH 3) 6.83 (t, 1H, O CH F 2, J = 76.8Hz) 8.79 (d, 1H, pyrimidine -H ^6, J = 4.8Hz Production Example 3 (Compound (4)) 2- (6-o-hydroxyphenyl-2-pyridyl) -4-methylpyrimidine obtained in II) of Production Example 2)
1 g and potassium hydroxide 20 mg were dissolved in dimethylformamide 10 ml. This solution was heated to 60 ° C., and Teflon (CF ₂ = C
F ₂ ) Gas was passed for one hour.

The reaction solution was extracted by adding 50 ml of water and 100 ml of ethyl acetate,
The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure.

The obtained residue was treated with silica gel column chromatography (eluent; hexane: ethyl acetate = 3: 1 (v / v)) to give 4-methyl-2- (6- (o-1,1,2,2). -Tetrafluoroethoxyphenyl) -2-pyridyl) pyrimidine
0.52 g was obtained.

mp 77.2 ° C PMR (CDCl ₃ ) δ ppm 2.62 (s, 3H, -CH ₃ ) 6.27 (tt, 1H, OCF ₂ CF ₂ H , J = 3.6 Hz, J = 53.4 Hz) 7.17 (d, 1H, pyrimidine-H ⁵ , J = 4.8 Hz) 8.78 (d, 1 H, pyrimidine-H ⁶ , J = 4.8 Hz) Production Example 4 (Compound (6)) 2- (6-o-) obtained in II) of Production Example 2 above. (Hydroxyphenyl-2-pyridyl) -4-methylpyrimidine
1 g was dissolved in 10 ml of DMF, and sodium hydride (60%
0.17 g). After returning to room temperature and stirring for 10 minutes, 0.5 g of propargyl bromide was added and reacted for 2 hours.
The reaction solution was poured into ice water (100 ml), and ethyl acetate (50 ml ×
Extracted in 3).

The organic layer was sufficiently washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure.

The obtained residue was treated with silica gel column chromatography (eluent; hexane: ethyl acetate = 3: 1 (v / v)) to give 4-methyl-2- (6- (o-propargyloxyphenyl-2-pyridyl). ) 0.93 g of pyrimidine was obtained.

▲ n ²⁶ _D ▼ 1.6136 PMR (CDCl ₃ ) δppm 2.61 (s, 3H, -CH ₃ ) 4.69 (d, 2H, -CH ₂ C≡CH, J = 2.4 Hz) 7.72 (t, 1H, pyrimidine-H ⁴ , J = 7.2Hz) 8.71 (d , 1H, pyrimidine -H ^6, J = 4.8Hz) production example 5 (compound (5)) is prepared example except using allyl bromide 0.51g instead of propargyl bromide 0.5g By the same operation as in 4-, 2- (6-o
0.85 g of-(allyloxyphenyl-2-pyridyl) -4-methylpyrimidine was obtained.

▲ n ²⁶ _D ▼ 1.6244 PMR (CDCl ₃ ) δppm 2.58 (s, 3H, -CH ₃ ) 7.64 (t, 1H, pyrimidine-H ⁴ , J = 7.2 Hz) 8.30 (dd, 1H, pyrimidine-H ³ , J = 1.8Hz, 7.2Hz) 8.63 (d , 1H, several pyrimidine -H ^6, J = 4.8Hz) the compound of the present invention obtained by these production methods are shown in table 1.

Next, formulation examples are shown. The compounds of the present invention are shown by the compound numbers in Table 1 and parts are parts by weight.

Formulation Example 1 50 parts of each of the compounds of the present invention (1) to (6), 3 parts of calcium ligninsulfonate, 2 parts of sodium lauryl sulfate and 45 parts of synthetic hydrous silicon oxide are thoroughly pulverized and mixed, and a wettable powder of each of the compounds of the present invention is prepared. Get.

Formulation Example 2 25 parts of each of the present compounds (1) to (6), 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC and 69 parts of water
Of the active ingredient are mixed and wet-pulverized until the particle size of the active ingredient becomes 5 μm or less to obtain a suspension of each compound of the present invention.

Formulation Example 3 Two parts of each of the present compounds (1) to (6), 88 parts of kaolin clay and 10 parts of talc are thoroughly pulverized and mixed to obtain a powder of each of the present compounds.

Formulation Example 4 20 parts of each of the compounds of the present invention (1) to (6), 14 parts of polyoxyethylene stilphenyl ether, 6 parts of calcium dodecylbenzenesulfonate, and 60 parts of xylene are mixed well to prepare an emulsion of each compound of the present invention. obtain.

Formulation Example 5 Two parts of each of the compounds of the present invention (1) to (6), 1 part of synthetic hydrous silicon oxide, 2 parts of calcium ligninsulfonate, 30 parts of bentonite and 65 parts of kaolin clay are thoroughly pulverized and mixed, and water is added. After kneading, the mixture is granulated and dried to obtain granules of the compound of the present invention.

Next, Test Examples show that the compounds of the present invention are useful as fungicides. The compounds of the present invention are indicated by the compound numbers in Table 1, and the compounds used for comparison are indicated by the compound symbols in Table 2.

The control effect was evaluated by visually observing the disease state of the test plant at the time of the survey, ie, the degree of fungal alga and lesions on leaves and stems, and if no fungal alga or lesion was observed, "5", about 10% "4" when recognized, "3" when recognized about 30%, "2" when recognized about 50%, "1" when recognized about 70%, and the disease state when the compound is not used for more than that If no difference is found, it is evaluated as “0” and evaluated on a 6-point scale.
5,4,3,2,1,0.

Test Example 1 Rice Blast Control Test (Preventive Effect) A plastic pot was filled with sandy loam, and rice (Kinki 33
No.) and raised in a greenhouse for 20 days. To a rice seedling, a test agent prepared as a suspension in accordance with Formulation Example 2 was diluted with water to a predetermined concentration, and the resulting solution was sprayed on foliage so as to sufficiently adhere to the leaves. After spraying, the plants were air-dried and sprayed and inoculated with a spore suspension of the blast fungus. After the inoculation, the plants were placed at 28 ° C. in the dark and in a humid environment for 4 days, and the control effect was examined. Table 3 shows the results.

Test Example 2 Rice blast control test (therapeutic effect) A plastic pot was filled with sandy loam, and rice (Kinki 33
No.) and raised in a greenhouse for 20 days. Rice seedlings were sprayed and inoculated with a spore suspension of the blast fungus. After inoculation, the specimen was left at 28 ° C. in the dark and in a humid environment for 16 hours, and then diluted with water to a predetermined concentration according to Formulation Example 1 so that it adhered sufficiently to the leaves. Foliage. After spraying, the plants were grown for 3 days at 28 ° C. in the dark and in a humid environment, and the control effect was examined. Table 4 shows the results.

Test Example 3 Wheat Powdery Mildew Control Test (Therapeutic Effect) A plastic pot was filled with sandy loam,
No.) was raised in a greenhouse for 10 days. Young seedlings of wheat were inoculated with powdery mildew fungi. After inoculation, the cells were grown at 23 ° C. for 3 days, and then diluted with water to a predetermined concentration according to Formulation Example 1, and sprayed with foliage so as to adhere sufficiently to the leaves. After spraying, grow in a greenhouse at 23 ° C for 7 days,
The control efficacy was investigated. Table 5 shows the results.

Test Example 4 Wheat blight control test (preventive effect) A plastic pot was filled with sandy loam, and wheat (agriculture and forestry 73
No.) and reared in a greenhouse for 8 days. A test solution prepared as a wettable powder according to Formulation Example 1 was diluted with water to a predetermined concentration and sprayed on a wheat seedling so as to adhere sufficiently to the leaves. After spraying, the plants were air-dried and spray-inoculated with a spore suspension of Fusarium head blight. After inoculation, 15 ℃, dark and humid
The plants were grown for 10 days under illumination at 15 ° C., and their control efficacy was investigated. The results are shown in Table 6.

Test Example 5 Barley Netting Disease Control Test (Preventive Effect) A plastic pot was filled with sandy loam, and barley (Akagami Riki) was cultivated for 14 days in a greenhouse. A barley seedling was diluted with water to a predetermined concentration by emulsifying the reagent according to Formulation Example 4 with water, and sprayed with foliage so as to sufficiently adhere to the leaves. After spraying, the plants were air-dried, sprayed with a spore suspension of the fungus spot, and inoculated. After inoculation, 3 in darkness and high humidity at 15 ℃
After standing for 20 days, the plants were grown for another 14 days under illumination at 20 ° C., and the control effect was examined. Table 7 shows the results.

Test Example 6 Barley scald disease control test (control effect) A plastic pot was filled with sandy sand, barley (Akagami power) was cultivated, and grown in a greenhouse for 14 days. A barley seedling was diluted with water to a predetermined concentration by emulsifying the reagent according to Formulation Example 4 with water, and sprayed with foliage so as to sufficiently adhere to the leaves. After spraying, the plants were air-dried, sprayed with a spore suspension of the fungus, and inoculated. After inoculation, 15 ℃, dark and humid
After standing for 20 days, the plants were grown for another 14 days under illumination at 20 ° C., and the control effect was examined. Table 8 shows the results.

Test Example 7 Wheat eye spot control test (therapeutic effect)
No.) was raised in a greenhouse for 10 days. Wheat seedlings were sprayed and inoculated with a spore suspension of the fungus spotted fungus. After inoculation,
After 2 days at 15 ° C., in the dark and in a humid environment, the test agent prepared as a wettable powder according to Formulation Example 1 was diluted with water to a predetermined concentration.
It was sprayed with foliage so that it adhered sufficiently to the leaf surface. After spraying, the plants were grown for 14 days under lighting and high humidity, and their control efficacy was investigated. Table 9 shows the results.

Test Example 8 Apple Scab Control Test (Preventive Effect) A plastic pot was filled with sand sand, apples were seeded, and grown in a greenhouse for 20 days. A test solution prepared as an emulsion according to Formulation Example 4 was diluted with water to a predetermined concentration, and sprayed onto apple seedlings so as to sufficiently adhere to the leaves.
After spraying, a spore suspension of apple scab was sprayed and inoculated. After the inoculation, the plants were left under humid conditions at 15 ° C. for 4 days, and then grown under illumination for 15 days, and the control effect was examined. The results are shown in Table 10.

Test Example 9 Cucumber Gray Mold Control Test (Preventive Effect) A plastic pot was filled with sand sand, cucumber (Sagami Hanjiro) was cultivated and grown in a greenhouse for 14 days. A test solution prepared as a wettable powder according to Formulation Example 1 was diluted with water to a predetermined concentration to a cucumber seedling, and the foliage was sprayed so as to sufficiently adhere to the leaf surface. After spraying, the plants were air-dried and inoculated with hyphae of MBC resistant gray mold. After inoculation, the plants were placed in a dark, humid environment at 15 ° C. for 3 days, and the control effect was examined. The result is
Table 11 shows.

Test Example 10 Rice Sheath Blight Control Test (Preventive Effect) A plastic pot was filled with sand sand and rice (Kinki 33
No.) and grown in a greenhouse for 28 days. A test solution prepared as a wettable powder according to Formulation Example 1 was diluted with water to a predetermined concentration, and the rice seedling was sprayed with foliage so as to sufficiently adhere to the leaves. After spraying, the plants were air-dried, sprayed with a bacterial agar-containing suspension of sheath blight, and inoculated. After the inoculation, the plants were placed at 28 ° C. in the dark and in a humid environment for 4 days, and the control effect was examined. The result is
See Table 12.

Test Example 11 Wheat Leaf Blight Control Test (Preventive Effect)
No.) and reared in a greenhouse for 8 days. A reagent prepared as an emulsion according to Formulation Example 4 was diluted with water to a predetermined concentration to a wheat seedling and sprayed so that it adhered sufficiently to the leaves. After air-drying, a spore suspension of the fungus was spray-inoculated. After inoculation, leave for 3 days at 15 ° C, dark and humid,
The plants were grown under illumination at 23 ° C. for 14 days, and their control efficacy was examined. Table 13 shows the results.

 ──────────────────────────────────────────────────続 き Continued on the front page (72) Inventor Kiyoto Maeda 4-2-1 Takashi, Takarazuka-shi, Hyogo Sumitomo Chemical Co., Ltd. (72) Inventor Masayo Kanno 4-2-1 Takashi, Takarazuka-shi, Hyogo Within Sumitomo Chemical Co., Ltd. (72) Norihisa Yamashita 4-2-1 Takashi Takarazuka-shi, Hyogo Prefecture Inside Sumitomo Chemical Co., Ltd. (56) Reference European publication 259139 (EP, A2) European publication 270362 (EP, A2) )

Claims (2)

(57) [Claims] (1) General formula Wherein, R ₁ represents a lower haloalkoxy group, a lower alkenyloxy group or lower alkynyloxy group, R ₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a lower haloalkyl group or a halogen atom, R ₃ Represents a hydrogen atom or a lower alkyl group, and R ₄ represents a lower alkyl group. ] The pyridyl pyrimidine derivative represented by these. 2. A fungicide for agricultural and horticultural use comprising the pyridylpyrimidine derivative according to claim 1 or a salt thereof as an active ingredient.