JPH03215471A - Pyridylamine derivative and fungicide for agricultural and horticultural use - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

DETAILED DESCRIPTION OF THE INVENTION Technical Field of the Invention The present invention relates to a novel compound and an agricultural and horticultural fungicide containing the compound as an active ingredient.

Technical Background of the Invention Nitrogen-containing heterocyclic compounds, typified by biridyl compounds, have been developed as active ingredients for agricultural and horticultural fungicides.

Examples of such nitrogen-containing heterocyclic compounds include:
3-(o-chlorophenyl)-2-(3-biridyl)propionitrile is known as a substance that inhibits the function of the adrenal cortex (US Pat. No. 3,198.158. Chemical Abstracts 59, P
114 49d etc.). However, this compound is different from the compound according to the present invention, and does not disclose any agricultural or horticultural fungicide.

In addition, examples of pyridylacetonitrile fungicides include Che1cal Abstracts 104
, 188422: 101. Compounds disclosed in No. 23355 and the like are known, but these have different carbon skeleton structures from the compounds of the present invention, and their bactericidal action is not necessarily satisfactory. In particular, the action against gray mold is not satisfactory.

On the other hand, as azolylacetonitrile fungicides, for example, the compounds disclosed in JP-A-61-187668 are known, but these compounds are structurally different from the compounds of the present invention, and moreover, they are The bactericidal activity of is not always satisfactory.

Further, JP-A No. 80-13780 discloses antifungal amine fungicides, and JP-A No. 60-138
559 discloses 2-(3-pyridyl)-2-phenylaminoacetic acid fungicides, but these compounds are also structurally different from the compounds of the present invention, and
Their fungicidal activity is not always satisfactory.

A large number of nitrogen-containing heterocyclic compounds have been known since the late 1960s, but these compounds generally have problems in that they cause phytotoxicity to plants, especially growth inhibition, and there is a need for improvement in this respect. .

Purpose of the Invention The purpose of the present invention is to provide an agricultural and horticultural fungicide that fully exhibits the excellent effects of a nitrogen-containing heterocyclic compound as a fungicide and does not cause phytotoxicity to plants, especially growth inhibition. There is.

Summary of the Invention The novel compound according to the present invention is characterized by being a pyridylamine derivative represented by the following formula (13), a salt of the derivative, or a metal complex of the derivative.

[In the formula, X and Y represent the same or different hydrogen atoms, halogen atoms, or phenylethynyl groups, R1, R2
represent the same or different lower alkyl groups. however,
It is assumed that X and Y do not represent hydrogen atoms at the same time. ] Furthermore, the agricultural and horticultural fungicide according to the present invention is characterized in that it contains as an active ingredient at least lftt selected from the pyridylamine derivative represented by the above formula (1), a salt of the derivative, and a metal complex of the derivative. There is.

DETAILED DESCRIPTION OF THE INVENTION A pyridylamine derivative, which is one of the novel compounds according to the present invention, has the structure shown in [1] above.

However, in the above formula [1], X represents a halogen atom or a group selected from F, Cl, Br and engineering, preferably F, C, l! , Br, and a phenylethynyl group.

Y is F, IJI. Represents a halogen atom selected from Br and I, preferably Cfi.

Rt and R2 are methyl group, ethyl group, n-
A straight or branched lower alkyl group having 1 to 6 carbon atoms such as propyl group, i-propyl group, butyl group, i-butyl group, sec-butyl group, bentyl group, i-pentyl group, hexyl group, etc. and R and R2 may be the same or different.

R1 and R2 are each preferably a methyl group, ethyl group or n-propyl group.

The pyridylamine derivative, which is one of the novel compounds according to the present invention, has optical isomers because it has an asymmetric carbon atom, and the pyridylamine derivative according to the present invention consists of each isomer and a mixture thereof. In the case of mixtures,
The abundance ratio of each isomer depends on the type of substituent, manufacturing conditions, etc., and is not necessarily constant.

The novel compounds according to the present invention also include salts and metal complexes of the above-mentioned pyridylamine derivatives.

In this case, the salt of a pyridylamine derivative means a salt of a biologically acceptable organic or inorganic acid and a pyridylamine derivative. Here, oxalic acid, etc. can be used as the organic acid, and hydrochloric acid, hydrobromic acid, etc. can be used as the inorganic acid.
Sulfuric acid, sulfonic acid, etc. can be used.

Moreover, the metal complex of a pyridylamine derivative means a metal complex of a metal salt compound and a pyridylamine derivative. Examples of metal salt compounds here include compounds having aluminum ions, manganese ions, cobalt ions, iron ions, nickel ions, copper ions, zinc ions, cadmium ions, etc. as cations, and chloride ions as counter ions to the cations. Anions such as , bromide ion, iodide ion, sulfate ion, phosphate ion, nitrate ion, carbonate ion, and acetate ion can be used. Particularly preferred among such metal salt compounds is cupric chloride.

The novel compounds according to the present invention include the above-mentioned biridylamine derivatives, salts of these derivatives, and metal complexes of these derivatives. Hereinafter, these may be collectively referred to as "compounds of the present invention."

Next, a method for producing the compound of the present invention will be explained.

The biridylamine derivative represented by the formula CI) is prepared by combining, for example, a compound represented by the following formula (II) and an organic halogen compound represented by the following formula (III) in an amount of usually 1 to 2 equivalents, such as NaH or KH. In the presence of organometallic compounds such as alkali metal hydrides and butyllithium,
It can be produced by reacting in a solvent at a temperature range from -78°C to the boiling point of the solvent for 1 hour to 24 hours.

[In formula (II), X, Y and R are the same as in the above [I] formula 1. ] R2-X'・・・・・・・・・・・・・・・
......[m'+[Formula (m], R1 is the above C
It is the same as the formula I], and X' represents a /% rogen atom such as iodine or bromine. ] Examples of the solvent used in the above production method include ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, and diethylene glycol dimethyl ether, as well as dimethylacetamide, dimethylformamide, and dimethyl sulfoxide. After the reaction has stopped, the reaction solution is poured into water and subjected to usual post-treatments such as extraction with an organic solvent to obtain the above formula CI).
The compound shown is obtained. At this time, purification by recrystallization or the like may be performed if necessary.

Note that the compound represented by the above formula [■] is, for example, the compound represented by the following formula (
IV) and usually 1.5 to 4
It can be produced by reacting an equivalent amount of an organometallic compound represented by the following formula (V) in a solvent at a temperature ranging from -78°C to the boiling point of the solvent for 1 hour to 24 hours.

[In formula (IV), X and Y are the same as the above-mentioned CI] formula. ]

R, -L ・・・・・・・・・・・・・・・
・・・・・・・・・[V) [Formula [V], R1 is the above-mentioned [I
] is the same as the formula, and L is lithium or the formula MgZ (
In the formula, Z represents a chlorine atom, a bromine atom, or an iodine atom] The solvent used in the above production method includes benzene,
Examples include aromatic hydrocarbons such as toluene and xylene, and ethers such as diethyl ether, diisobupylether, dioxane, tetrahydrofuran, and diethylene glycol dimethyl ether.

After the reaction has been terminated, the compound represented by the above formula [■] is obtained by performing a usual post-treatment such as pouring the reaction solution into a saturated aqueous ammonium chloride solution and extracting with an organic solvent. At this time, purification by recrystallization or the like may be performed if necessary.

Next, salts of biridylamine derivatives and metal complexes of biridylamine derivatives according to the present invention will be explained.

The above salts and metal complexes generally have the following formula (Vl)
It is indicated by.

[In the formula [VT], X, Y, R and R2 are the same as in the above formula 1 (IE), and Q represents a biologically acceptable organic acid, inorganic acid or metal salt compound.] The chemically acceptable organic acids, inorganic acids, or metal salt compounds are as described above, and the organic acids that can be used include oxalic acid, and the inorganic acids that can be used include hydrochloric acid, hydrobromic acid, sulfuric acid, Sulfonic acid, etc. can be used. Also, examples of metal salt compounds include compounds having aluminum ions, manganese ions, cobalt ions, iron ions, nickel ions, copper ions, zinc ions, cadmium ions, etc. as cations. As counter ions for cations, anions such as chloride ions, bromide ions, iodine ions, sulfate ions, phosphate ions, nitrate ions, carbonate ions, and acetate ions can be used. Among these metal salt compounds, Particularly preferred is cupric chloride.

The biridylamine derivative salt represented by the formula [VI] is
The pyridylamine derivative represented by the above formula [1] and Q(
(organic acid, inorganic acid, or metal salt compound) in an alcohol such as ethanol or methanol, or a solvent such as diethyl ether, acetone, or water at a temperature from room temperature to the boiling point of the solvent. In addition, at this time, purification by +1 crystal etc. may be performed as necessary.

The compounds of the invention as described above have prophylactic, therapeutic or systemic bacterial activity against many plant pathogens.

When the compound of the present invention is used as an agricultural or horticultural fungicide, it may be used as it is without adding any other ingredients, but it is usually added with a solid carrier, liquid carrier, surfactant, or formulation auxiliary agent. It may also be used by mixing with other substances and preparing emulsions, permanent agents, suspensions, granules, etc. These preparations contain the compound of the present invention as an active ingredient in a weight ratio of 0.1 to 99.B%,
It is preferably contained in an amount of 0.2 to 80%.

As the solid carrier, fine powders or granules such as kaolin clay, attabulgite clay, bentonite, acid clay, pie phyllite, talc, diatomaceous earth, calcite, and synthetic hydrous silicon oxide can be used, and these can be used alone or in combination. Can be used in combination.

Liquid carriers include aromatic hydrocarbons such as xylene and methylnaphthalene; alcohols such as isopropanol, ethylene glycol, and cellosolve; acetone; ketones such as cyclohexanone and isophorone; vegetable oils such as soybean oil and cottonseed oil;
Examples include dimethylsulfoquine and acetonitrile, and these can be used alone or in combination.

Surfactants used for emulsification, dispersion, wetting, etc. include alkyl sulfate salts, alkyl (aryl) sulfonate salts, dialkyl sulfosuccinate salts, polyoxyethylene alkylaryl ether phosphate salts, and naphthalene sulfonic acid salts. There are anionic surfactants such as formalin condensates, nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene polyoxypropylene block copolymer sorbicun fatty acid ester, etc., and these may be used alone or in combination. I can do it.

Pharmaceutical auxiliaries include lignin sulfonate, alginate, polyvinyl alcohol, gum arabic, carboxymethyl cellulose, isobrovir acid phosphate, etc., and these can be used alone or in combination.

When using the agricultural and horticultural fungicide according to the present invention as a powder,
0.5 to 50 parts by weight of the compound of the present invention, 50 to 50 parts by weight of the solid carrier
It is preferable to blend the compound in an amount of 95.5 parts by weight, more preferably 1 to 30 parts by weight of the compound of the present invention and 70 to 99 parts by weight of the solid carrier.

When using the agricultural and horticultural fungicide according to the present invention as a permanent agent, the compound of the present invention is contained in 5 to 95 parts by weight, and the liquid carrier is contained in 5 to 95 parts by weight.
It is preferable to blend the compound of the present invention in a ratio of 10 to 75 parts by weight, and the solid carrier in an amount of 25 parts by weight.
It is desirable to blend in a proportion of ~90 parts by weight.

When using the agricultural and horticultural fungicide according to the present invention as an emulsion,
5 to 90 parts by weight of the compound of the present invention and 0.1 to 90 parts by weight of the surfactant
It is preferable to blend the compound of the present invention in an amount of 10 parts by weight, more preferably 10 to 80 parts by weight of the compound of the present invention, and 0.1 to 10 parts by weight of the surfactant. This emulsion also contains 10-8% of other components such as a liquid carrier.
It can also be added in a proportion of about 9.9 parts by weight.

When using the agricultural and horticultural fungicide according to the present invention, there is no necessarily limit to the amount of spraying, but usually when spraying on fields where crops are grown, the compound of the present invention is 1 to 500 g per 10 are. It is preferable to spread the liquid to a certain extent. When applied to soil, it is appropriate to use the compound of the present invention in an amount of about 0.1 to 5 kg per 10 ares.

Of course, this is just a guideline, and it may be adjusted as necessary, taking into account factors such as the type of crop, the type of disease, the degree of damage, the season, the weather, and the dosage form of the drug.

The compounds of the present invention are effective in controlling a wide range of diseases of agricultural and horticultural crops, and the main ones include the following.

Water Rice: Blast, sesame leaf blight, sheath blight, stupid seedling disease, seedling blight, etc. Wheat: Fusarium rust, yellow rust, naked smut, leaf blight, spot disease, brown snow rot, Powdery mildew, etc. Potatoes: Phytophthora, summer blight, black spot, etc. Soybeans: Downy mildew, leaf spot, brown spot, sclerotium, rust, purpura, etc. Azuki beans: brown spot, Rust, sooty blight, powdery mildew, etc. Peanut: brown spot, black astringent blight, sclerotium, etc. Tobacco: red blight, late blight, sclerotium, buckthorn blight, fly blight, white star blight, powdery mildew Beet: downy mildew, brown spot, seedling damping off, etc. Vegetable tomato: gray mold, leaf mold, late blight, sclerotium, ring spot, sooty mold, wilt, seedling damping off Diseases such as eggplant: gray mold, half-wilt, brown rot, black blight, powdery mildew, sooty mold, etc. Cucurbits: downy mildew, gray late blight, gray mold, sclerotinia,
Scotch blight, anthracnose, vine blight, vine splitting blight, powdery mildew, seedling blight, etc.Chinese cabbage: downy mildew, white spot blight, sclerotium blight, clubroot blight, etc.Onion; white blight, downy mildew diseases, gray rot, anthracnose, etc. Lettuce: downy mildew, gray mold, brown spot, sclerotium, etc. Strawberry: gray mold, powdery mildew, ring spot, etc. Ornamental plants Chrysanthemum: white rust, Powdery mildew, etc. Cyclamen: Botrytis, etc. Rose: Botrytis, powdery mildew, etc. Fruit trees: Citrus: Blue mold, Botrytis, black spot, scab, etc. Apple: Fusarium, leaf spot, scab, scab, etc. , powdery mildew, etc.: Downy mildew, black spot, black spot, etc. Downy mildew, downy mildew, gray mold, brown leaf rot, etc. Effects of the invention, such as disease, late rot, rust, Benabmostia vine blight, vine splitting disease, powdery mildew, etc. As explained above, the compound of the present invention has a wide range of excellent control effects for controlling diseases of agricultural and horticultural crops. It is highly effective, especially against gray mold. Therefore, when agricultural and horticultural fungicides containing the compounds of the present invention are used in fields, they are extremely effective and long-lasting. Furthermore, the excellent effects exhibited by the compounds of the present invention are manifested not only in preventive applications but also in therapeutic applications.

Furthermore, the compound of the present invention not only has the above-mentioned control effect, but also has the extremely useful property of causing almost no phytotoxicity to plants, especially field crops such as tomatoes, cucumbers, eggplants, green peppers, root vegetables, etc.

EXAMPLES Hereinafter, the present invention will be explained using specific examples, but the present invention is not limited to these examples.

Preparation Example 1 of the Compound of the Present Invention Synthesis of Compound 9 35% Potassium in 20 ml of anhydrous tetrahydrofuran
4.3 g of oil dispersion of hydride was suspended and cooled to 0°C, and 5.3 g of anhydrous tetrahydride was suspended and cooled to 0°C. Add LO ml of the furan solution dropwise under a nitrogen stream. 0 again after stirring at room temperature for 1 hour.
The mixture was cooled to 0.degree. C., and a solution of 5.64 g of iodomethane in 10 ml of anhydrous tetrahydrofuran was added dropwise.

After stirring at room temperature for 3 hours, pour into a large amount of water and extract with dichloromethane. After drying over anhydrous magnesium sulfate, the solvent was distilled off and the residue was subjected to silica gel chromatography and eluted with a mixed solvent of hexane and ethyl acetate to obtain a pale yellow oil. Yield was 3.0g. The obtained compound was designated as Compound 9, and the NMR Wl determination results of Compound 9 are shown in Table-1.

Note that NMR measurements were performed using deuterated chloroform (CDC) as a solvent.
g3) and TMS (tetramethylsilane) was used as an internal standard. The same will be displayed below.

Example 2 Synthesis of Compound 2 Anhydrous N.I. 3506 in 20ml of N-dimethylformamide
Potassium hydride oil disversion 2.3
Suspend 2.7 g of anhydrous N. N-dimethylformamide 10
ml was added dropwise under a nitrogen stream. After stirring at room temperature for 1 hour, it was cooled to 0°C and 2 g of iodomethane was added to anhydrous N.I. Add 5 ml of N-dimethylformamide dropwise and stir at room temperature for 5 hours. The mixture is poured into a large amount of water, extracted with diethyl ether, dried over anhydrous sodium sulfate, the solvent is distilled off, and the residue is subjected to silica gel chromatography to obtain a pale yellow oil. Yield was 2.1g.

Example 3 Synthesis of Compound 14 1-(2-
Chloro-4-fluorophenyl)-1(N-pyridine-
12 ml of a 1.6 mol hexane solution of butyl lithium dissolved in 5.3 g of 3-yl) aminobutyl lithium under a nitrogen stream
After stirring at -78℃ for 1 hour, add iodobroban 5
．． Slowly add 5 ml of a solution of 1 g of anhydrous tetrahydride in furan. After dropping, the mixture was returned to room temperature and stirred at room temperature for an additional 5 hours. The mixture was poured into ice water, extracted with diethyl ether, dried over anhydrous sodium sulfate, and the solvent was distilled off, leaving a yellow oil as a residue. Apply silica gel chromatography and develop with a mixed solvent of hexane and ethyl acetate to obtain the desired product.

Yield was 6.7g.

Example 4 Synthesis of Compound 41 1 g of Compound 9 was dissolved in 10 ml of diethyl ether and stirred at room temperature. A solution of 0.32 g of oxalic acid in 15 ml of diethyl ether was added dropwise and stirred at room temperature for 3 hours.

The solid formed is quenched with suction and washed with diethyl ether. Yield was 1.3g.

Example 5 Synthesis of Compound 40 15.4 g of cupric chloride dihydrate: 50 ml of ethanol
Compound 9 25. while stirring at room temperature. lr
50 ml of ethanol solution was slowly added dropwise and stirred at room temperature for 3 hours. Add 200 ml of water, thoroughly crush the lumps in water, and then evaporate with suction. The yield was 35.0g.

Table 1 shows NMR IJ1 results for other compounds obtained in the same manner as in the above examples. In addition,
From now on, explanations may be made using the compound numbers in the table.

Next, for reference, a method for synthesizing one of the synthetic intermediates of the compound of the present invention will be exemplified.

Reference example intermediate 1- (2-chloro-4-fluorophenyl)-
Synthesis of 1-(N-pyridin-3-yl)aminopyridine 23.7 g of N-(2-chloro-4-fluorobenzylidene)-3-aminopyridine was added to 100 ml of a 3 molar tetrahydrofuran solution of ethylmagnesium bromide at room temperature.
ml of tetrahydrofuran solution was added dropwise with stirring, and the mixture was refluxed for 3 hours. Return to room temperature, pour into 2N hydrochloric acid solution, stir at room temperature for 30 minutes, and then make alkaline with sodium carbonate. Extract with dichloromethane, wash with water, dry, and evaporate the solvent to obtain a brown solid. Run a short column of silica gel with a mixed solvent of hexane and ethyl acetate.
Get 1 item. The yield was 18.1g.

Medicinal Efficacy Test In order to specifically explain the effects of the compounds of the present invention, the following tests were conducted. However, these are merely examples, and it goes without saying that the application examples of the present invention are not limited to these.

The comparative compounds are shown in Table 9. Also in the table (a
．． i. ．． ppo+) indicates the concentration of the active ingredient.

Test Example 1 Cucumber Powdery Mildew Efficacy Test A potted cucumber (variety: Aio Hanpaku) was sprayed with an amount equivalent to 200 N/lOa of a chemical solution diluted to a predetermined concentration at the two-leaf stage, and then air-dried at room temperature.

After air-drying, the treated cucumber seedlings were left in a greenhouse and infected with powdery mildew fungus (Sphacrotheca ruljgin).
ea) was naturally infected. After 14 days of standing, an investigation was conducted according to the following criteria. However, the consecutive losing streak was 5 consecutive times, and a total of 10 leaves were investigated.

n: Number of leaves by degree of disease f: Index by degree of disease N = Number of examined leaves Index by degree of disease 0: Number of leaves without disease (accumulation of disease o96) 1: Few
(1-25%) 3: Medium (26-50%) 5: High
” ( 〃 51～1oro
%) The results are shown in Table-2.

Test Example 2 Wheat Rust Efficacy Test Potted wheat (variety: Norin No. 61) was infected with Puccinia recondita r.
sp. triticl) summer spores under a microscope at 100x1
A suspension adjusted to 20 cells per field of view was spray inoculated.

Immediately after inoculation, the plants were kept in the dark at a temperature of 23° C. and a humidity of 100% for 28 hours, and then left in a greenhouse. On the third day after inoculation, an amount equivalent to 200N/10a of a chemical solution diluted to a predetermined concentration was sprayed. An investigation was conducted on the 10th day after inoculation according to the following criteria. However, the number of runs shall be 5.

n: Number of leaves by degree of disease f: Index by degree of disease N = Number of examined leaves Index by degree of disease 0: Number of leaves without disease (with disease 0?o) 1: Few
// ( /〆 l~25%) 3, medium 〃 (l/
26-50%) 5: High (51-100%) Results are shown in Table 3
Shown below.

Test Example 3 Cucumber Gray Mold Efficacy Test An amount equivalent to 20 Jl/10a of a chemical solution diluted to a predetermined concentration was sprayed onto the third leaf of a potted cucumber (variety: Yotsuba).

After air-drying indoors for 24 hours, Botryti
commercially available yeast extract (1% equivalent ffi) and commercially available glucose (10%
ffi) was added and spray inoculated. Immediately after vaccination,
Keep it in the dark for 3 days at a temperature of 22℃ and a humidity of 100%.
The investigation was conducted according to the following criteria. However, the number of runs shall be 8.

Σnr n: Number of leaves by disease severity f: Index by disease severity N: Number of inspected leaves Index by disease severity 0: Number of disease-free leaves (affected area 0%) 1: Small (No/1~
25%) 3: Medium (26-50%) 5: High (/51-100%) The results are shown in Table 4.

Test Example 4 Bean Sclerotinia Disease Efficacy Test Cut the primary leaves of green beans (variety: Masterpiece) and apply 20ml of the drug solution diluted to a specified concentration on 10 primary leaves.
After spraying and air-drying indoors, bean Sclerotinia fungi (Sclerotinia bacterium) cultured in PDA medium in advance
sclerotiorum) was punched out with a cork borer and inoculated. Immediately after inoculation, the plants were kept in a constant temperature room at a temperature of 28° C. and a humidity of 100% for 4 days, and then the diseased area was investigated.

However, 10 primary leaves were examined as 10 consecutive losses.

The results are shown in Table-5.

Test Example 5 Rice Blast Efficacy Test An amount equivalent to 200 R/loa of a chemical solution with a predetermined concentration was sprayed on potted rice plants (variety Nijukoku) at the 3-leaf stage.

Rice blast fungus (Pyricular) cultured after air drying
A suspension of conidia of S. iaoryzae was adjusted to 40 conidia per field of view under a microscope at 100x magnification and was inoculated by spraying.

Immediately after inoculation, the plants were kept under dark conditions at a temperature of 23°C and a humidity of 100% for 48 hours, and then left in a greenhouse. Ten days after inoculation, the degree of disease onset was determined using the following criteria.

However, the number of runs shall be three.

n = Number of leaves by severity of disease f: Index by severity of disease N = Number of leaves examined Index by severity of disease Number of lesions per leaf 00 1l 2　　　　　　2～5 3　　　　　　6～10 ４　　　　　　11〜 The results are shown in Table-6.

Test Example 6 Rice sheath blight efficacy test A chemical solution of a predetermined concentration was sprayed onto the primary leaves of green beans (variety: Masterpiece), and then air-dried indoors.

After air-drying, the rice sheath blight fungus (Rhiz
octonia solani IA) was punched out with a cork borer and inoculated.

After inoculation, the seeds were left in the dark at a temperature of 28° C. and a humidity of 100% for 3 days to check for the presence or absence of disease.

However, a losing streak will be defined as 5 consecutive losses.

The results are shown in Table-7.

Test Example 7 Sustainability test using eggplant gray mold efficacy test At the 4-leaf stage of potted eggplant (cultivar No. 2,000 Ryo 2), an amount equivalent to 200R/IOa of a chemical solution diluted to a constant concentration of f was applied to each seed. Spray C 1 day before, 4 days before, 7 days before, and 10 days before the day of inoculation, and glass a! Managed internally. These were put together and Botrytis cinerea C (Botrytis cinerea
) were spray-inoculated in the same manner as in Test Example 32, and the following procedures were carried out in the same manner.

The results are shown in Table-8.

Table-2 Cucumber powdery mildew efficacy test Table 3 Wheat rust efficacy test 1/1 Table-4 Cucumber botrytis mildew efficacy test Compound concentration Incidence No. (a.i., p1) lf! ) 13.0 IO. 0 15.5 25.0 26.5 8,5 9,5 25. O I5,0 25,a 15,O 25.0 2B,5 28,0 25,0 25 0 25.0 25,0 25.0 45,O lO. 0 25,0 13.0 100 Jusei Inhibition Table-5 Bean Sclerotinia Disease Efficacy Test t Agricultural Rate (a.i.・ppm) 500 Control Value Table Rice Sheath Blight Efficacy Test Compound Nα Concentration (a.i. , I) pill) Control value table-8 Persistence test compound concentration powder against gray mold of eggplant/1i to inoculation [Incidence per number 147 10.0 12.0 45.010.0
15.5 4B. 58.0 10.0 1
2.0 g. 0 1Q. 0 12.5 10.0 12.0 43.512.0
15.5 18.5100

Claims (2)

[Claims] (1) General formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [In the formula, X and Y represent the same or different hydrogen atoms, halogen atoms, or phenylethynyl groups, and R_1, R
_2 represents the same or different lower alkyl groups. However, X and Y do not represent hydrogen atoms at the same time. ] A pyridylamine derivative, a salt of the derivative, or a metal complex of the derivative, characterized by the following: (2) General formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [In the formula, X and Y represent the same or different hydrogen atoms, halogen atoms, or phenylethynyl groups, and R_1, R
_2 represents the same or different lower alkyl groups. However, X and Y do not represent hydrogen atoms at the same time. ] An agricultural and horticultural fungicide characterized by containing as an active ingredient at least one selected from the following pyridylamine derivatives, salts of the derivatives, and metal complexes of the derivatives.