JP2000103784A - 5-alkoxypyrazole-3-carboxamide derivative and agrochemical with the same as active ingredient - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject a highly safe new compound having highly controlling effect even on various germs resistant to conventional agricultural/ horticultural germicides, mitigated in such problems as residual toxicity and environmental pollution, therefore useful as an active ingredient of agricultural/ horticultural germicides. SOLUTION: This new compound is represented by formula I (R1 is a 1-4C alkyl, allyl or 1-4C haloalkyl; R2 is a halogen, a 1-4C alkyl, nitro or the like; Y is CH or N), e.g. N-n-propyl-1-(4-cyanophenyl)-5-methoxypyrazole-3- carboxamide. The compound of formula I is obtained, for example, by reaction between a compound of formula II (Z is chlorine, bromine, OH or the like) [e.g. ethyl 1-(4-cyanophenyl)-5-methoxypyrazole-3-carboxylate] and a compound of the formula n-C3H7NH2 in the presence or absence of a solvent pref. at 20-80 deg.C. The compound of formula I has highly germicidal effect on various plant germs such as Pyricularia oryzae, rust fungi and Plasmapara viticola.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a novel 5-alkoxypyrazole-3-carboxamide derivative and a pesticide containing the same as an active ingredient, particularly a fungicide.

[0002]

2. Description of the Related Art In the field of agriculture and horticulture, various fungicides for controlling various diseases have been developed and put to practical use. However, conventional agricultural and horticultural fungicides are not always satisfactory in terms of bactericidal effect, bactericidal spectrum or residual effect. Further, the demands such as reduction of the number of times of application and the amount of applied medicine have not been satisfied.

[0003] In addition, the emergence of pathogenic bacteria that have acquired resistance to conventional agricultural chemicals has also become a problem. For example, in the cultivation of vegetables, fruit trees, flowers, tea, wheat, rice, and the like, various types of pesticides, for example, triazole, imidazole, pyrimidine, benzimidazole, dicarboximide, and phenylamide pesticides. Various pathogens which have acquired resistance have emerged in various places, and it has become difficult year by year to control various diseases caused by these pathogens.

[0004] Further, there are pesticides such as dithiocarbamate-based or phthalimide-based pesticides, for which pathogenic bacteria have not yet acquired resistance, but these are generally large in the amount of applied drug and the number of times of application, and are preferable from the viewpoint of environmental pollution and the like. Not something.
Therefore, even with various pathogens that have acquired resistance to conventional general-purpose agricultural and horticultural fungicides, they show a sufficient control effect at low doses,
In addition, there is a strong need for the development of a novel bactericide that has little adverse effect on the environment.

[0005] It is known that pyrazolecarboxamide derivatives have physiological activities such as insecticidal, acaricidal, fungicidal, herbicidal and medicinal activities, respectively, depending on the three substituents on the pyrazole ring and the type of amino group of the carboxamide moiety. Have been. For example, 1-phenylpyrazole-3-carboxamide derivative is disclosed in JP-A-64-25763.
No. includes N-aralkyl having insecticidal and acaricidal activity.
1-phenylpyrazole-3-carboxamide derivatives have been reported. Japanese Unexamined Patent Publication No. 63-91373 discloses N-alkyl-
4-halogeno-5-unsubstituted-1-phenylpyrazole-
3-carboxamide derivatives;
Japanese Patent Application Laid-Open No. 63-15867 discloses N-alkyl-4-unsubstituted-5-alkyl-1-phenylpyrazole-3-carboxamide derivatives; , 5-Diphenylpyrazole-3-
Although carboxamide derivatives are described, they do not describe bactericidal activity at all. Further, N-alkyl-4-halogeno-1,5-diphenylpyrazole-3-carboxamide having herbicidal activity has been disclosed in JP-A-8-12.
No. 654, but no description of the bactericidal activity.

Furthermore, N-alkyl- having a pharmaceutically active property
4-Unsubstituted-5-alkoxy-1-phenylpyrazole-3-carboxamide derivatives are described in Pharmaceutical Journal, 97, 71
9 (1977) and Journal of Med
Ial Chemistry, vol. 20, p. 80 (19
77), but nothing about the pesticidal activity. Also, N-methyl-4-bromo-5-methoxy-1-phenylpyrazole-3-carboxamide was reported in Nagoya City University Pharmaceutical School Annual Report, Vol. 29, p. 25 (1).
981), but it has no medicinal activity and no description of pesticide activity. As described above, there is no report on the bactericidal activity of the 5-alkoxypyrazole-3-carboxamide derivative.

[0007]

DISCLOSURE OF THE INVENTION The present invention has a high control effect on various pathogenic bacteria which are resistant to conventional fungicides for agricultural and horticultural use, and reduces problems such as residual toxicity and environmental pollution. Another object of the present invention is to provide a highly safe chemical substance useful as an active ingredient of an agricultural and horticultural fungicide.

[0008]

The present inventors have made intensive efforts to solve the above problems, and as a result, can solve the above problems by using a novel 5-alkoxypyrazole-3-carboxamide represented by the following formula. This led to the completion of the present invention. That is, the gist of the present invention is represented by the following general formula (I)

[0009]

Embedded image

Wherein R ¹ is a C ₁ -C ₄ alkyl group;
An allyl group or a C ₁ -C ₄ haloalkyl group;
² represents a halogen atom, a C ₁ -C ₄ alkyl group, a nitro group, a cyano group or a trifluoromethyl group, and Y represents CH or a nitrogen atom), and a 5-alkoxypyrazole-3-carboxamide derivative represented by the formula: The present invention relates to pesticides containing this compound as an active ingredient.

As mentioned above, pharmaceutically active 5-alkoxypyrazole-3-carboxamide derivatives are known. However, the pharmaceutical journal most similar to the present invention,
97, p. 719 (1977).
-Alkoxy-1-substituted phenylpyrazole-3-carboxamide derivatives are methyl, dimethyl, diisopropyl, n-butyl,
2-diethylaminoethyl, ethyl, diethyl, sec
Although compounds of -butyl and 2-hydroxyethyl are shown, compounds of n-propyl group as the N-alkyl group are not described. No pyridyl group is described as a substituent at the 1-position. Moreover, there is no description about pesticide activity. And, as is clear from the test examples described later, the compound in which the N-substituent of carboxamide is an n-propyl group has excellent pesticidal activity as compared with the corresponding compound in which the N-substituent is a methyl group. I have.

[0012]

BEST MODE FOR CARRYING OUT THE INVENTION In the general formula (I), R ¹ is specifically a methyl group, an ethyl group, an n-propyl group,
Isopropyl group, n-butyl group, sec-butyl group, t
Linear or branched C ₁ -C ₄ alkyl groups such as -butyl group; C ₁ -C ₄ haloalkyl groups such as allyl group, difluoromethyl group, trichloromethyl group and pentafluoroethyl group. R ² is a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom and an iodine atom; a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a cyclopropyl group, an n-butyl group, an isobutyl group, and a sec-
C ₁ -C ₄ linear, branched or cyclic alkyl groups such as butyl group and t-butyl group, nitro group, cyano group and trifluoromethyl group. The compound represented by the general formula (I) can be produced, for example, according to the following reaction formula.

[0013]

Embedded image

(In the above formula, R ¹ , R ² and Y are as defined in the above general formula (I), and Z represents a chlorine atom, a bromine atom, a hydroxyl group, a methoxy group, an ethoxy group or a propoxy group. ).

In the general formula (II), when Z represents a chlorine atom or a bromine atom, aromatic solvents such as benzene, toluene and xylene as solvents; ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone; Halogenated hydrocarbons such as chloroform and methylene chloride; water; esters such as methyl acetate and ethyl acetate; or tetrahydrofuran, acetonitrile, dioxane,
A polar solvent such as N, N-dimethylformamide, N-methylpyrrolidone or dimethylsulfoxide is used.
The reaction can be carried out in the presence of a base at from 0 to 30 ° C, preferably from 0 to 5 ° C. As the base, for example, sodium hydroxide, potassium hydroxide, pyridine or triethylamine can be used.

In the general formula (II), when Z is a hydroxyl group, a methoxy group, an ethoxy group or a propoxy group, an alcohol such as methyl alcohol, ethyl alcohol or propyl alcohol may be used in the absence of a solvent. The reaction can be carried out in a solvent at 5 to 100 ° C, preferably 20 to 80 ° C. After the reaction, in order to isolate the target compound represented by the general formula (I), when a solvent soluble in water is used, the solvent is distilled off under reduced pressure, and water is added. Aromatic hydrocarbons such as benzene, toluene, and xylene insoluble in water; halogenated hydrocarbons such as chloroform and methylene chloride; extracted with esters such as ethyl acetate, washed with brine, and dried over anhydrous sodium sulfate What is necessary is just to dry with an agent and distill off the solvent under reduced pressure. When a solvent insoluble in water is used, water is added to the reaction mixture, and the mixture is separated. The organic layer is washed with saturated saline, dried with a desiccant such as anhydrous sodium sulfate, and then the solvent is distilled off under reduced pressure. I just need.

The residue obtained after distilling off the solvent may be a pure product as it is, but if it is impure, it may be washed with a hydrocarbon such as hexane or heptane or the like which does not substantially dissolve the target compound, or recrystallized or purified. Purification by column chromatography gives a pure product. Compounds represented by the general formula (II) are described, for example, in Pharmaceutical Journal, Vol. 97, p. 719 (197)
7) and the Journal of Medical C
The compound can be synthesized according to the method described in Chemistry, vol. 20, p. 80 (1977).

The compound of the present invention represented by the general formula (I)
It has a high bactericidal effect against various plant pathogenic fungi such as blast fungus, rust fungus, downy mildew fungus and plague fungus, and is useful as an active ingredient of pesticides, especially fungicides for agricultural and horticultural use. However, the phytopathogenic bacteria to be controlled by the compound of the present invention are not limited to those exemplified above. General formula (I)
When the compound of the present invention is used as a pesticide, for example, a fungicide for agricultural and horticultural use, it may be used alone, but preferably used as a composition to which a pesticide adjuvant widely used in the art is added. Is preferred. The dosage form of the fungicide for agricultural and horticultural use is not particularly limited, but is preferably in the form of, for example, emulsion, wettable powder, powder, flowable, fine granule, granule, tablet, oil, spray, aerosol, etc. It is. One or more of the above compounds can be blended as an active ingredient.

Agrochemical auxiliaries used for producing agricultural and horticultural fungicides include, for example, improvement of the effect of agricultural and horticultural fungicides;
A substance having an effect of stabilizing and improving dispersibility, for example, a carrier (diluent), a spreading agent, an emulsifier, a wetting agent, a dispersant, a disintegrant, and the like can be used. Examples of the liquid carrier include water; aromatic hydrocarbons such as toluene and xylene; alcohols such as methanol, butanol, and glycol; ketones such as acetone; amides such as dimethylformamide; sulfoxides such as dimethyl sulfoxide; methylnaphthalene Cyclohexane; animal and vegetable oils; and fatty acids. As the solid carrier, for example, clay, kaolin, talc, diatomaceous earth, silica, calcium carbonate, montmorillonite, bentonite, feldspar, quartz, alumina, sawdust, nitrocellulose,
Starch, gum arabic and the like. Usable emulsifiers and dispersants include ordinary surfactants, for example, anionic surfactants such as higher alcohol sodium sulfate, stearyltrimethylammonium chloride, polyoxyethylene alkylphenyl ether, lauryl betaine; A nonionic surfactant; a zwitterionic surfactant; or the like can be used. A spreading agent such as polyoxyethylene nonyl phenyl ether and polyoxyethylene lauryl phenyl ether; a wetting agent such as dialkyl sulfosuccinate; a fixing agent such as carboxymethyl cellulose and polyvinyl alcohol; sodium lignin sulfonate and sodium lauryl sulfate; Can be used.

The content of the active ingredient in the fungicide for agricultural and horticultural use of the present invention is selected from the range of 0.1 to 99.5%, and may be appropriately determined according to various conditions such as the form of the preparation and the method of application. For example, in the case of powder, about 0.5 to 20% by weight,
It is preferably 1 to 10% by weight, about 1 to 90% by weight, preferably 10 to 80% by weight for a wettable powder, and about 1 to 10% by weight for an emulsion.
About 90% by weight, preferably 10 to 40% by weight, and about 1 to 90% by weight, preferably 10 to 5% for a flowable agent.
It is preferred to prepare them so as to contain 0% by weight of the active ingredient.

For example, in the case of an emulsion, an emulsion of a stock solution can be prepared by mixing a solvent, a surfactant and the like with the above-mentioned compound which is an active ingredient. Dilute with and apply. In the case of a flowable agent, an undiluted solution can be produced by mixing water, a surfactant, and the like with the compound as an active ingredient,
Further, this undiluted solution is diluted with water to a predetermined concentration before use. In the case of a wettable powder, the compound is prepared by mixing the above-mentioned compound of the active ingredient, a solid carrier, a surfactant and the like, and further diluted with water to a predetermined concentration before use. In the case of powder,
The compound of the active ingredient, the solid carrier and the like can be mixed and applied as it is. In the case of granules, the compound is produced by mixing and granulating the compound of the active ingredient, the solid carrier and the surfactant and the like. And can be applied as is. However, the production method of each of the above-mentioned preparation forms is not limited to the above-mentioned method, and can be appropriately selected by those skilled in the art according to the kind of the active ingredient, the purpose of application, and the like.

The agricultural and horticultural fungicides of the present invention include other fungicides, insecticides, acaricides, herbicides, insect growth regulators, fertilizers, as long as the activity of the compound of the present invention as an active ingredient is not impaired. Any active ingredient such as a soil conditioner may be added.
The method for applying the agricultural and horticultural fungicide of the present invention is not particularly limited, and it can be applied by any method such as foliage application, water surface application, soil treatment, seed treatment and the like. For example,
In the case of foliage application, 5 to 1,000 ppm, preferably 1
A solution having a concentration range of 0 to 500 ppm can be used at an application rate of about 100 to 200 L per 10 ares.
In the case of water application, the application amount is usually 5 to 15% of the active ingredient.
Is 10 to 10 kg per 10 ares. In the case of soil treatment, a solution having a concentration range of 5 to 1,000 ppm can be used at an application rate of about 1 to ¹⁰ L per m ² . In the case of seed treatment, 10 to 10 kg of seed weight
10 to 100 ml of a solution in a concentration range of 1,000 ppm
The degree of application can be treated.

[0023]

EXAMPLES The present invention will be described in more detail with reference to the following examples, preparation examples and test examples, but the present invention is not limited to the following examples as long as the gist of the present invention is not exceeded. In addition,
The preparation examples of a part of the starting materials of the following examples are shown as reference examples.

Reference Example 1 Synthesis of ethyl 1- (4-chlorophenyl) -5-difluoromethoxypyrazole-3-carboxylate 20.0 g of chlorodifluoromethane gas was blown into 100 ml of dry ethyl alcohol to give 1- (4-chlorophenyl). ) -5-Hydroxypyrazole-3-carboxylate (10.0 g) and potassium carbonate (7.31 g) were added, and the mixture was heated in an autoclave at 70 ° C for 2 hours. After cooling to room temperature, the mixture was concentrated under reduced pressure. Water was added to the obtained residue, extracted with ethyl acetate, and washed with saturated saline. Separate the organic phase,
After concentration under reduced pressure, the residue was purified by silica gel column chromatography to obtain 7.51 g of ethyl 1- (4-chlorophenyl) -5-difluoromethoxypyrazole-3-carboxylate, mp 94 to 95 ° C. ¹ H-NMR (CDCl ₃ ) δ ppm: 1.41 (3
H, t, J = 7.2 Hz), 4.43 (2H, q, J =
7.2 Hz), 6.56 (1H, t, J = 7.1H)
z), 6.60 (1H, s), 7.45 (2H, d, J
= 9 Hz), 7.60 (2H, d, J = 9 Hz).

Reference Example 2 Synthesis of ethyl 1- (4-cyanophenyl) -5-difluoromethoxypyrazole-3-carboxylate 1- (4-cyanophenyl) -5 in the same manner as in Reference Example 1.
-Hydroxypyrazole-3-carboxylate is reacted with chlorodifluoromethane to give the desired product, mp137-
138 ° C. was obtained. ¹ H-NMR (CDCl ₃ ) δ ppm: 1.42 (3
H, t, J = 7.2 Hz), 4.44 (2H, q, J =
7.2 Hz), 6.61 (1H, t, J = 7.1H)
z), 6.62 (1H, s), 7.79 (2H, d, J
= 9 Hz), 7.88 (2H, d, J = 9 Hz).

Reference Example 3 Synthesis of ethyl 1- (5-chloropyridin-2-yl) -5-methoxypyrazole-3-carboxylate 1- (5-chloropyridin-2-yl) -5-hydroxypyrazole 29.6 g of ethyl-3-carboxylate, 21.9 g of potassium carbonate and 17.0 g of dimethylsulfuric acid were heated and refluxed in 150 ml of ethanol for 5 hours. After concentration under reduced pressure, water was added to the residue, and the mixture was extracted with ethyl acetate. The organic phase was separated, washed with water and saturated saline, and dried over anhydrous sodium sulfate. After concentration under reduced pressure, the residue was washed with hexane-acetone to obtain 15.8 g of the desired product, mp 117-118 ° C. ¹ H-NMR (CDCl ₃ ) δ ppm: 1.41 (3
H, t, J = 7.2 Hz), 4.03 (3H, s),
4.24 (2H, q, J = 7.2 Hz), 6.24 (1
H, s), 7.95-8.07 (3H, m), 8.51.
(1H, s).

Reference Example 4 1- (5-trifluoromethylpyridin-2-yl) -5-methoxypyrazole-
Synthesis of ethyl 3-carboxylate 1- (5-trifluoromethylpyridin-2-yl) -5-hydroxypyrazole-3- in the same manner as in Reference Example 3.
The reaction between ethyl carboxylate and dimethyl sulfate
mp 85-86 ° C. ¹ H-NMR (CDCl ₃ ) δ ppm: 1.42 (3
H, t, J = 7.2 Hz), 4.06 (3H, s),
4.44 (2H, q, J = 7.2 Hz), 6.26 (1
H, s), 7.95-8.08 (3H, m), 8.83.
(1H, s).

Reference Example 5 Synthesis of ethyl 1- (4-cyanophenyl) -5-methoxypyrazole-3-carboxylate 1- (4-cyanophenyl) -5 in the same manner as in Reference Example 3.
Ethyl-hydroxypyrazole-3-carboxylate was reacted with dimethyl sulfate to obtain the desired product, mp 123 to 125 ° C. ¹ H-NMR (CDCl ₃ ) δ ppm: 1.42 (3
H, t, J = 7.2 Hz), 4.04 (1H, s),
4.43 (2H, q, J = 7.2 Hz), 6.24 (1
H, s), 7.73 (2H, d, J = 9 Hz), 7.9
8 (2H, d, J = 9 Hz).

<Example 1> Nn-propyl-1-
(4-bromophenyl) -5-methoxypyrazole-3
Synthesis of 1- (4-bromophenyl) -5-methoxypyrazole-3-carboxylic acid 0.59 g and 4 ml of thionyl chloride in 1
Heated to reflux for an hour. After unreacted thionyl chloride was distilled off under reduced pressure, the residue was dissolved in 10 ml of toluene. This solution is
A solution of 0.59 g of propylamine and 1.01 g of triethylamine in 10 ml of toluene was added dropwise at 0 to 10C. After the dropwise addition, the mixture was stirred at room temperature for 2 hours, then poured into ice water and extracted with toluene. The toluene phase was washed with water and saturated saline in this order, dried over anhydrous sodium sulfate, and then toluene was distilled off under reduced pressure. The residue was washed with hexane.
The compound (No. 3) described in No. 1 was obtained. Melting point 75-77
° C.

<Example 2> Nn-propyl-1-
(4-cyanophenyl) -5-methoxypyrazole-3
Synthesis of -carboxamide 1- (4-cyanophenyl) -5 obtained in Reference Example 5
0.54 g of ethyl methoxypyrazole-3-carboxylate
Was stirred in 2.36 g of n-propylamine at room temperature for 8 hours. The reaction solution was concentrated under reduced pressure, and the obtained residue was washed with hexane to obtain a compound (No. 11) described in Table 1 (0.45).
g was obtained. The melting point was 146-147 ° C.

<Example 3> According to the method of Example 1 or Example 2, the compounds shown in Table 1 were obtained.

[0032]

[Table 1]

<Formulation Example 1> Wettable powder The compound No. of the present invention 9 (hereinafter, compound No.
Compound No. Corresponding to ), 20 parts by weight of Carplex # 80 (white carbon, Shionogi & Co., Ltd., trade name), 52 parts by weight of ST kaolin clay (Kaolinite, Tsuchiya Kaolin Co., Ltd.), and Solpol 9047K (anionic) 5 parts by weight of a surfactant, Toho Chemical Co., Ltd., and 3 parts by weight of Lunox P65L (anionic surfactant, Toho Chemical Co., Ltd.) are mixed and uniformly mixed and pulverized to obtain an active ingredient of 20%. % By weight of wettable powder was obtained.

<Formulation Example 2> Dust The compound No. of the present invention 11, 2 parts by weight of clay, 93 parts by weight of clay (manufactured by Nippon Talc), and 5 parts by weight of Carplex # 80 (white carbon, Shionogi & Co., Ltd., trade name) are uniformly mixed and pulverized to obtain 2% by weight of the active ingredient. Was manufactured.

Formulation Example 3 Emulsion Compound No. of the present invention 11 in 20 parts by weight, xylene 35
In a mixed solvent consisting of 30 parts by weight of dimethylformamide and 30 parts by weight of dimethylformamide, and sorbol 3005X (a mixture of a nonionic surfactant and an anionic surfactant,
Toho Chemical Co., trade name (15 parts by weight) was added to obtain an emulsion containing 20% by weight of the active ingredient.

<Formulation Example 4> Flowable agent Compound No. of the present invention. 11 for 30 parts by weight, Solpol 9
5 parts by weight of 047K, 3 parts by weight of Sorbone T-20 (a nonionic surfactant, trade name of Toho Chemical Co., Ltd.), 8 parts by weight of ethylene glycol and 44 parts by weight of water with Dynomill (manufactured by Shinmaru Enterprises). Wet grinding,
10 parts by weight of a 1% by weight aqueous solution of xanthan gum (natural polymer) is added to the slurry-like mixture, mixed well and pulverized.
A flowable containing 20% by weight of the active ingredient was obtained.

<Test Example 1> Sterilization effect on rice blast 10 rice plants (variety: Akinishiki) were grown per pot in a resin pot having a diameter of 6 cm. The fungicide (emulsion) for agriculture and horticulture of the present invention prepared according to the formulation of Formulation Example 3 was diluted with water to a predetermined concentration and sprayed on the rice (3 to 4 leaf stage) at a ratio of 10 ml per pot with foliage. After air-drying the sprayed drug solution, the rice was spray-inoculated with a spore suspension (5.0 × 10 ⁵ spores / ml) of rice blast fungus (Magnaporthe grisea) cultured in an oatmeal medium and sprayed on a moist chamber at 25 ° C. Hold for 24 hours. Then, it was left to stand in a greenhouse (22 to 25 ° C.) for 7 days, the area ratio of the appeared lesions was measured, and the control value was calculated by the following formula. Table 2 shows the results.
It was shown to. In addition, Compound No. Is the compound No. in Table 1.
Corresponding to

[0038]

(Equation 1)

<Comparative Test Example 1> Pharmaceutical Magazine, 97, 71
The bactericidal effect against the blast fungus was tested in the same manner as in Test Example 1 using the following compound described on page 9 (1977).
The results are shown in Table-2.

[0040]

Embedded image

[0041]

[Table 2] Compound No. Concentration (ppm) Control value (%) {1 500 100 3 500 100 9 500 100 11 11 500 100 12 500 100}比較 Comparative Example 1 500 0 ─────────────────────── ─

Test Example 2 Bactericidal Effect Against Tomato Blight Three rice strains (variety: red cherry) were grown per pot in a resin pot having a diameter of 6 cm. Compound No. prepared according to the formulation of Formulation Example 1. Eleven agricultural and horticultural fungicides (wettable powders) were diluted to 500 ppm with water and sprayed on the rice (3-4 leaf stage) at a rate of 10 ml per pot. After the sprayed chemical solution was air-dried, the rice plant was cultivated on cut tomato leaves, and Phytophthor was cultivated.
a infestans zoospore suspension (5.0 ×
10 ⁴ zoospores / ml) were spray-inoculated and kept in a humidity chamber at 25 ° C. for 24 hours. Then, in a greenhouse (20-22 ° C.)
After leaving for days, the area of the lesions appearing in the leaves was measured and indicated by a disease index, and the control value was calculated by the following formula. The control value was 100%.

[0043]

[Table 3]

[0044]

(Equation 2) _nx : number of tomato leaves with the disease index x per pot

[0045]

(Equation 3)

[0046]

Industrial Applicability The 5-alkoxypyrazole-3 of the present invention
-Carboxamides have an excellent control effect on various plant pathogens, and are useful as agricultural and horticultural fungicides.

Claims (2)

[Claims] 1. A compound represented by the following general formula (I) (In the formula, R ¹ represents a C ₁ -C ₄ alkyl group, an allyl group or a C ₁ -C ₄ haloalkyl group, and R ² represents a halogen atom, a C ₁ -C ₄ alkyl group, a nitro group, a cyano group. Or a trifluoromethyl group, and Y represents CH or a nitrogen atom).
-Carboxamide derivatives. 2. An agricultural chemical containing the 5-alkoxypyrazole-3-carboxamide derivative according to claim 1 as an active ingredient.