JPH11199566A - 1-substituted pyrazole-3-carboxamide derivative and germicide containing the same derivative as active ingredient - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject new compound having a (substituted)phenyl or a (substituted)2-pyridyl at 1 position, reduced in residual toxicity and environmental contamination, capable of exhibiting high safety and high controlling effect on and various kinds of pathogenic fungus and useful as a germicide for agriculture or horticulture. SOLUTION: This compound is represented by formula I [A is a group of formula II (R<2> to R<4> are each H, a halogen, a 1-5C alkyl, CF3 or the like) or a group of formula III (R6 to R8 are each R<2> ); R<1> is a 1-4C alkyl or a 1-4C alkoxy; R<5> is a (1-5C alkyl)amino, pyrrolidinyl, morpholino or the like; X is a halogen; Y is O or S], e.g. N-n-propyl-4-bromo-1-(4-chlorophenyl)-5- methylpyrazole-3-carboxamide. The compound of formula I is obtained by reacting a compound of formula IV (Z is Cl, Br, OH or the like) with a compound of the formula R<5> H.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a novel 1-substituted-pyrazole-3-carboxamide derivative and a fungicide for agricultural and horticultural use containing the same as an active ingredient.

[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-based, imidazole-based, pyrimidine-based, benzimidazole-based, dicarboximide-based, phenylamide-based pesticides, and the like. 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] On the other hand, pyrazolecarboxamide derivatives are based on the three substituents on the pyrazole ring and the type of amino group of the carboxamide moiety, and the insecticide, miticide,
It is known to have a physiological activity such as herbicidal activity or pharmaceutical activity. For example, a 1-phenylpyrazole-3-carboxamide derivative is disclosed in JP-A-64-2576.
No. 3 reports an N-aralkyl-1-phenylpyrazole-3-carboxamide derivative having insecticidal and acaricidal activity. JP-A-63-91373 discloses an N-alkyl-4-halogeno-5-unsubstituted-1-phenylpyrazole-3-carboxamide derivative as a substance having a harm-reducing action of a herbicide;
No. 4 discloses an N-alkyl-4-unsubstituted-5-alkyl-1-phenylpyrazole-3-carboxamide derivative; and JP-A-63-115867 discloses an N-alkyl-4-unsubstituted derivative. 1,5-diphenylpyrazole-3
-Carboxamide derivatives are described, but they do not disclose any bactericidal activity. Further, N-alkyl-4-halogeno-1,5-diphenylpyrazole-3-carboxamide having herbicidal activity has been disclosed in JP-A-8-1.
No. 2,654, but no bactericidal activity is described.

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, Nagoya City University Faculty of Pharmaceutical Sciences Annual Report,
29, 25 (1981), N-methyl-4-bromo-5-methoxy-1-phenylpyrazole-3-carboxamide was synthesized to search for a substance having an analgesic action. No effect was noted. No mention is made of the pesticidal activity of this compound. As described above, there is no report on a 1-phenylpyrazole-3-carboxamide derivative having a bactericidal activity.

[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, a novel 1-substituted-pyrazole-3-carboxamide derivative represented by the following formula has the above characteristics. The present invention was found to be a compound, and the present invention was completed. That is, the gist of the present invention is represented by the following general formula (I)

[0009]

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(Where A is

[0011]

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Wherein R ¹ is a C ₁ -C ₄ alkyl group or a C ₁ -C ₄ alkoxy group, and R ² , R ³ , R
⁴ , R ⁶ , R ⁷ and R ⁸ each independently represent a hydrogen atom, a halogen atom, a C ₁ -C ₅ alkyl group, a trifluoromethyl group, a nitro group, a cyano group, a C ₁ -C ₄ alkoxy group, haloalkoxy groups _{C 1 ~C 4, C 2 ~C} 5
Alkoxycarbonyl group, an alkylcarbamoyl group of C ₂ -C _5, an alkylthio group of _{C 1 ~C 4, C 1 ~C} 4
Alkylsulfinyl group, an alkylsulfonyl group having C ₁ -C _4, an amino group, an alkylamino group of C ₁ -C _4,
Dialkylamino group C ₂ -C _4, have a C ₂ -C alkylcarbonylamino group _5, C ₂ -C ₅ alkoxycarbonylamino group, alkylsulfonylamino group or substituent of C ₁ -C ₄ A good phenoxy group, X represents a halogen atom, Y represents an oxygen atom or a sulfur atom, R ⁵ is an amino group, a C ₁ -C ₅ alkylamino group, a C ₂ -C ₄ dialkylamino group, Pyrrolidinyl group, morpholino group, 2,6-dimethylmorpholino group,
Allylamino group, propargylamino group, methoxyamino group, methoxypropylamino group, 2,2,2-trifluoroethylamino group, cyanomethylamino group, C ₁ to
C _{4 represents} an alkylhydrazino group or an allylhydrazino group. However, when R ¹ is a methoxy group and R ⁵ is an alkylamino group, the alkylamino group has 2 to 5 carbon atoms. )) And a fungicide for agricultural and horticultural use containing this derivative as an active ingredient.

Hereinafter, the present invention will be described in detail. General formula
The substituent R of the compound of the present invention represented by (I)¹Is
Group, ethyl group, n-propyl group, isopropyl group,
Chloropropyl group, n-butyl group, isobutyl group, sec
-Butyl group, t-butyl group, etc.₁~ C_FourStraight chain, branched
Chain or cyclic alkyl group; methoxy group, ethoxy
Group, n-propoxy group, isopropoxy group, n-butoxy
Si, isobutoxy, sec-butoxy, t-butoxy
C such as xyl group₁~ C_FourStraight or branched chain alkoxy
Represents a group. R¹As C ₁~ C_TwoAlkyl group, tool
Physically, methyl, ethyl, methoxy, etc. are preferred.
And particularly preferably a methoxy group.

R^Two, R^Three, R^Four, R⁶, R⁷And R⁸
Are each independently a hydrogen atom; a fluorine atom, a chlorine atom,
Halogen atom of iodine atom; methyl group, ethyl
Group, n-propyl group, isopropyl group, cyclopropyl
Group, n-butyl group, isobutyl group, sec-butyl group,
C such as t-butyl group, n-pentyl group, isoamyl group, etc. ₁
~ C_FiveLinear, branched or cyclic alkyl groups;
Fluoromethyl group; nitro group; cyano group; methoxy group;
Toxic group, n-propoxy group, isopropoxy group, n-
Butoxy group, isobutoxy group, sec-butoxy group, t
-C such as butoxy group₁~ C_FourLinear or branched chain al
Coxy group; difluoromethoxy group, trifluoromethoxy
Si group, 2-fluoroethoxy group, 2-chloroethoxy
Group, 2,2,2-trifluoroethoxy group, 2,2,2
-Trichloroethoxy group, 3-chloropropoxy group, 3
-Bromopropoxy group, 3,3,3-trifluoropro
Poxy group, 2,2,3,3-tetrafluoropropoxy
Group, 2,2,3,3,3-pentafluoropropoxy
Group, 2,2-dichloro-3,3,3-trifluoropro
A oxy group, a 1,3-difluoro-2-propoxy group,
1,1,1,3,3,3-hexafluoro-2-propo
Xy group, 3,3,3-trichloropropoxy group, 4-c
Lolobutoxy group, 4,4,4-trifluorobutoxy
Group, 3,3,4,4,4-pentafluorobutoxy group, etc.
C₁~ C_FourA straight-chain or branched-chain haloalkoxy group;
Methoxycarbonyl group, ethoxycarbonyl group, n-propyl
Ropoxycarbonyl group, isopropoxycarbonyl group,
n-butoxycarbonyl group, isobutoxycarbonyl
Group, sec-butoxycarbonyl group, t-butoxycal
C such as bonyl group_Two~ C_FiveLinear or branched alkoxy
Cicarbonyl group; methylcarbamoyl group, dimethylcarb
Bamoyl group, ethylcarbamoyl group, diethylcarbamo
Yl, n-propylcarbamoyl, isopropyl
Rubamoyl group, n-butylcarbamoyl group, isobutyl
Carbamoyl group, sec-butylcarbamoyl group, t-
C such as butylcarbamoyl group_Two~ C_FiveStraight chain or minute
Branched alkylcarbamoyl group; methylthio group, ethyl
Thio group, n-propylthio group, isopropylthio group, n
-Butylthio group, isobutylthio group, sec-butylthio
C, e.g.₁~ C_FourStraight chain or
Branched alkylthio group; methylsulfinyl group, ethyl
Sulfinyl group, n-propylsulfinyl group, isop
Ropylsulfinyl group, n-butylsulfinyl group, i
Sobutylsulfinyl group, sec-butylsulfinyl
C, t-butylsulfinyl group, etc.₁~ C_FourStraight chain
Or a branched alkylsulfinyl group; methylsulfonyl
Group, ethylsulfonyl group, n-propylsulfonyl
Group, isopropylsulfonyl group, n-butylsulfonyl
Group, isobutylsulfonyl group, sec-butylsulfonyl group
C and t-butylsulfonyl groups₁~ C_FourStraight chain
Or branched alkylsulfonyl group; amino group; methyl
Amino group, ethylamino group, n-propylamino group, i
Isopropylamino group, n-butylamino group, isobutyl
Amino group, sec-butylamino group, t-butylamino
C such as a group₁~ C_FourLinear or branched alkylamino
Group: dimethylamino group, diethylamino group, methylethyl group
C such as ruamino group and methylpropylamino group_Two~ C_Fourof
Linear or branched dialkylamino group; acetylamino
C, such as a thio group, a propionylamino group and a butyrylamino group
_Two~ C_FiveLinear or branched alkylcarbonylamido
NO group: methoxycarbonylamino group, ethoxycarbonyl
C, such as amino group and propoxycarbonylamino group_Two~
C_FiveLinear or branched alkoxycarbonylamino of
Group: methylsulfonylamino group, ethylsulfonylamino
Group, propylsulfonylamino group, butylsulfonyl
C such as amino group₁~ C_FourLinear or branched alkyl of
Sulfonylamino group; alkyl such as methyl group and ethyl group
Group or halogen atom such as chlorine atom, bromine atom, etc.
And phenoxy groups and the like which may be used. X is a halogen atom
With a fluorine, chlorine, bromine or iodine atom
Is shown. X is particularly preferably a chlorine atom or a bromine atom.
No. Y represents an oxygen atom or a sulfur atom. In particular, R^Two,
R^ThreeAnd R^FourOne of or R⁶, R⁷And R⁸of
One of them is a halogen atom, an alkyl group, an alkoxy
Group, trifluoromethyl group, cyano group, haloalkoxy
Group, especially a trifluoromethoxy group, and
A substituent bound to the para-position of the bond to the sol ring
Preferably, there is.

R ² , R ³ , R ⁴ , R ⁶ , R ⁷ and R ⁸
Is preferably a hydrogen atom. R ⁵ is an amino group; a methylamino group, an ethylamino group, n
-Propylamino group, isopropylamino group, cyclopropylamino group, n-butylamino group, isobutylamino group, sec-butylamino group, t-butylamino group,
n- Amiruamino group, isoamyl group, t-Amiruamino group linear C ₁ -C _5, such as, an alkylamino group branched or cyclic; dimethylamino group, diethylamino group, methylethylamino group, methylpropylamino group, etc. dialkylamino group of C ₂ -C _4; pyrrolidinyl group;
Morpholino group; 2,6-dimethylmorpholino group; allylamino group; propargylamino group; methoxyamino group;
Methoxypropylamino group; 2,2,2-trifluoroethylamino group; cyanomethylamino group; methylhydrazino group, ethylhydrazino group, propylhydrazino group,
A C ₁ -C ₄ linear or branched alkylhydrazino group such as a butylhydrazino group; and an allylhydrazino group.
R ⁵ is preferably a C ₂ -C ₄ alkylamino group, particularly preferably a propylamino group.
When R ¹ is a methoxy group and R ⁵ is an alkylamino group, the alkylamino group has 2 to 5 carbon atoms, and particularly preferably an alkylamino group having 2 to 4 carbon atoms.
The compound of the present invention represented by the general formula (I) is a novel compound and can be produced, for example, according to the following reaction formula.

[0016]

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(Where A, R ¹ , R ⁵ , X and Y
Is defined as 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 above general formula (II), Z represents a chlorine atom, a bromine atom When the compound of the formula (1) is used as a starting material, aromatic hydrocarbons such as benzene, toluene and xylene; 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 a polar solvent such as tetrahydrofuran, acetonitrile, dioxane, N, N-dimethylformamide, N-methylpyrrolidone or dimethyl sulfoxide, and the like at 0 ° C to 30 ° C, preferably 0 ° C to The reaction can be performed at 5 ° C. in the presence of a base. 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, a compound such as methyl alcohol, ethyl alcohol, propyl alcohol, etc. 5 to 100 ° C, preferably 20 to 80 ° C in an alcohol solvent
To perform the reaction. 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 which are insoluble in water; halogenated hydrocarbons such as chloroform and methylene chloride; extraction with esters such as ethyl acetate;
After washing with a saturated saline solution, drying with a desiccant such as anhydrous sodium sulfate may be performed, and the solvent may be distilled off under reduced pressure. When a solvent insoluble in water is used, water is added to the reaction mixture, followed by separation,
The organic phase may be washed with saturated saline, dried with a desiccant such as anhydrous sodium sulfate, and the solvent may be distilled off under reduced pressure.

The residue obtained after distilling off the solvent may be a pure product as it is. If the residue is impure, the residue may be washed with a hydrocarbon such as hexane or heptane which does not substantially dissolve the target compound, or recrystallized or purified. Purification by column chromatography gives a pure product. In addition, the compound represented by the general formula (II) is, for example, Journal of Chemica
l Society, p. 3262 (1958), Jou
rnal of Chemical Society,
2769 (1961), Annalen Der C
Chemie, 716, 160 (1968), JP-A-63-91373 and JP-A-1-283274.
Gazette, Pharmaceutical Magazine, Vol. 97, p. 719 (1979) and Journal of Medical Chemis
try, 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 pathogens such as blast fungus, rust fungus, downy mildew fungus and plague fungus.As an active ingredient of agricultural and horticultural fungicides, cereals such as rice and barley, fruit trees and vegetables It is useful for the control of disease. However, crops and phytopathogenic fungi to be controlled by the compound of the present invention are not limited to those exemplified above.

When the compound of the present invention represented by the general formula (I) is used as a fungicide for agricultural and horticultural use, it may be used alone, but usually contains an agricultural chemical adjuvant commonly used in the art. It is preferably used as a composition. 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, the 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.

As the emulsifier and dispersant, ordinary surfactants can be used. For example, anionic surfactants such as higher alcohol sodium sulfate, stearyltrimethylammonium chloride, polyoxyethylene alkylphenyl ether, lauryl betaine, etc. A cationic surfactant; a nonionic surfactant; or an amphoteric surfactant. 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 compound of the general formula (I), which is an active ingredient of the agricultural and horticultural fungicide of the present invention, is 0.1 to 99.5%.
Is selected from the range. The dosage form 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 a powder, about 0.5 to 20% by weight, preferably 1 to 10% by weight,
For wettable powders, about 1 to 90% by weight, preferably 10 to 8% by weight.
0% by weight, about 1 to 90% by weight, preferably 10 to 40% by weight for emulsions, and about 1 to 90% by weight for flowables
It is preferable to produce the active ingredient so as to contain the active ingredient in an amount of preferably about 10 to 50% by weight.

For example, in the case of an emulsion, a stock solution of an emulsion can be prepared by mixing a solvent and a surfactant with the compound of the general formula (I) as an active ingredient. Diluted with water and applied. In the case of a flowable, a stock solution can be prepared by mixing water, a surfactant and the like with the compound of the general formula (I) as an active ingredient, and this stock solution is diluted with water to a predetermined concentration when used. And apply. In the case of wettable powders, the active ingredient is prepared by mixing the compound of the general formula (I) as an 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 a powder, the compound of the general formula (I) as an active ingredient, a solid carrier and the like can be mixed and applied as it is, and in the case of a granule, the compound of the general formula (I) as an active ingredient, a solid carrier and It can be produced by mixing and granulating a surfactant or the like, and can be applied as it 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 fungicide of the present invention contains other fungicides, insecticides, acaricides, herbicides, insect growth regulators as long as the activity of the compound of the general formula (I) as an active ingredient is not impaired. Any active ingredient such as an agent, a fertilizer, and a soil conditioner may be blended. 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, a solution having a concentration range of 5 to 1000 ppm, preferably 10 to 500 ppm can be used at an application rate of about 100 to 200 L (liter) per 10 ares. The application rate for water application is usually
For granules containing 5 to 15% of active ingredient, 1 to 10 ares
10 kg. 5 to 1000 ppm for soil treatment
Can be used at an application rate of about 1 to ¹⁰ L per m ² . For seed treatment, seed weight 1
1 to 10 ppm of solution per kg
About 0 to 100 ml can be applied.

[0027]

EXAMPLES Hereinafter, the present invention will be described more specifically with reference to examples and test examples, but the present invention is not limited to the following examples unless it exceeds the gist thereof. <Example 1> Nn-propyl-4-bromo-1-
(4-chlorophenyl) -5-methylpyrazole-3-
Synthesis of carboxamide 3.16 g of 4-bromo-1- (4-chlorophenyl) -5-methylpyrazole-3-carboxylic acid and 4 ml of thionyl chloride were mixed and heated under reflux for 1 hour. After unreacted thionyl chloride was distilled off under reduced pressure, the residue was dissolved in 10 ml of toluene. This solution was added dropwise to a solution of 0.59 g of n-propylamine and 1.01 g of triethylamine in 10 ml of toluene at 0 to 10 ° C. After the dropwise addition, the mixture was stirred at room temperature for 2 hours, and 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 the toluene was distilled off under reduced pressure. The residue was washed with hexane, and the compound (No.
9) 2.86 g was obtained. The melting point was 121-122 ° C.

Example 2 Synthesis of Nn-propyl-4-chloro-1- (4-chlorophenyl) -5-ethylpyrazole-3-carboxamide 4-chloro-1- (4-chlorophenyl) -5 3.15 g of ethyl ethylpyrazole-3-carboxylate and 2.95 g of n-propylamine were dissolved in 25 ml of methanol and stirred at room temperature for 32 hours. The reaction solution was concentrated under reduced pressure,
The obtained residue was purified by silica gel column chromatography, and 2.89 g of the compound (No. 24) shown in Table 1 was obtained.
I got Melting point was 98-99 ° C.

Example 3 Synthesis of Nn-propyl-4-chloro-1- (4-cyanophenyl) -5-methoxypyrazole-3-carboxamide 4-chloro-1- (4-cyanophenyl)- 3.06 g of ethyl 5-methoxypyrazole-3-carboxylate and n-
11.8 g of propylamine was added to 30 ml of methanol and stirred at room temperature for 40 hours. It gradually dissolved as the reaction proceeded. The reaction solution was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 2.51 g of the compound (No. 97) shown in Table 1. Melting point was 120-121 ° C. <Example 4> Tables were prepared according to the method of Example 1, 2 or 3.
The compounds described in 1, 2, and 3 were obtained.

[0030]

[Table 1]

[0031]

[Table 2]

[0032]

[Table 3]

[0033]

[Table 4]

[0034]

[Table 5]

[0035]

[Table 6]

[0036]

[Table 7]

[0037]

[Table 8]

[0038]

[Table 9]

[0039]

[Table 10]

[0040]

[Table 11]

[0041]

[Table 12]

[0042]

[Table 13]

[0043]

[Table 14]

[0044]

[Table 15]

[0045]

[Table 16]

Hereinafter, examples of the formulation of an agricultural and horticultural fungicide containing the compound of the present invention as an active ingredient are shown, but the form of the agricultural and horticultural agent of the present invention is not limited to the following. In addition,
Compound No. Is the compound No. in Tables 1, 2 and 3. Corresponding to <Production Example 1> Wetting agent Compound No. of the present invention. 9, 20 parts by weight of Carplex # 80 (white carbon, Shionogi & Co., Ltd., trade name), 20 parts by weight of ST kaolin clay (Kaolinite,
Tsuchiya Kaolin Company, 52 parts by weight, Solpol 90
47K (anionic surfactant, Toho Chemical Co., trade name) 5 parts by weight and Lunox P65L (anionic surfactant, Toho Chemical Co., trade name) 3 parts by weight are blended and uniformly mixed and pulverized. A wettable powder of 20% by weight of the active ingredient was obtained.

<Production Example 2> Dust The compound No. of the present invention 9, 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.

<Production Example 3> Emulsion Compound No. of the present invention 24 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.

<Production Example 4> Flowable agent Compound No. of the present invention. 17 30 parts by weight, Solpol 9
5 parts by weight of 047K, 3 parts by weight of Sorbone T-20 (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> Bactericidal effect on rice blast 10 rice plants (variety: Akinishiki) were grown per pot using 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 to a predetermined concentration with water and sprayed on the rice (3-4 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 then inoculated into a 25 ° C. wet chamber. 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 4 shows the results.
Shown in In addition, Compound No. Is the compound N in Table 1-3
o. Corresponding to

[0050]

(Equation 1)

<Comparative Test Example 1> The bactericidal effect against blast fungus was tested in the same manner as in Test Example 1 using the following compound described in JP-A-8-12654. The results are shown in Table-4.

[0052]

Embedded image

<Comparative Test Example 2> JP-A-1-283274
The bactericidal effect against blast fungus was tested in the same manner as in Test Example 1 using the following compounds described in No. The results are shown in Table-4.

[0054]

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<Comparative Test Example 3> JP-A-63-91373
The bactericidal effect against blast fungus was tested in the same manner as in Test Example 1 using the following compounds described in No. The results are shown in Table-4.

[0056]

Embedded image

[0057]

[Table 17] Table-4 {Compound No. concentration (ppm) Pest control value (%)} ─────────────────────────── 2500 100 6 500 100 7 500 100 8 500 500 100 9 500 100 10 500 100 11 500 95 12 500 100 14 500 100 15 500 100 16 500 100 100 17 500 100 100 18 500 100 19 19 500 100 23 23 500 100 24 500 100 27 27 500 87 29 500 100 32 500 100 33 500 100 35 500 100 36 500 100 37 500 100

[0058]

Table 18 (Continued) ──────────────────────────── Compound No. Concentration (ppm) Control value (%) ──────────────────────────── 38 500 100 39 500 97 42 42 500 94 43 500 500 98 44 500 100 45 500 500 46 500 100 47 500 100 48 500 100 49 500 100 50 500 500 100 51 500 100 100 52 500 100 53 500 100 54 500 100 55 55 500 100比較 Comparative Example 1 500 0 ────────────────────────────

[0059]

[Table 19] Table 4 (continued) ──────────────────────────── Compound No. Concentration (ppm) Control value (%) ５６ 56 500 100 57 500 100 58 500 500 100 59 500 100 60 500 100 61 61 500 98 66 500 98 67 500 100 69 500 100 70 500 95 71 500 90 90 73 500 100 74 500 100 75 75 500 100 76 500 100 100 77 500 100 78 500 500 100 79 500 100 82 500 100 83 500 100 84 500 100 90 500 100 91 500 100

[0060]

[Table 20] Table 4 (Continued) Compound No. Concentration (ppm) Control value (%) ──────────────────────────── 92 500 100 97 500 100 115 115 100 100 117 500 100 119 500 100 120 500 100 122 500 100 124 500 100 125 500 100 126 500 500 100 128 500 100 129 500 100 131 500 100 132 500 100 比較 Comparative Example 2 500 0 Comparative Example 3 500 0

Test Example 2 Bactericidal Effect Against Tomato Blight Three rice plants (variety: red cherry) were grown per pot in a resin pot having a diameter of 6 cm. The fungicide for agricultural and horticultural use (wettable powder) of the present invention formulated according to the formulation of Formulation Example 1 was diluted to a predetermined concentration with water, and 1 was added to the above rice (3-4 leaf stage).
Foliage was sprayed at a rate of 10 ml per pot. After the sprayed chemical solution was air-dried, the rice plant was cultured on cut tomato leaves and the tomato blight (Phytophthora infesta) was grown.
ns) zoosporangium suspension (5.0 × 10 ⁴ zoospores / m)
l) was spray inoculated and kept in a humidity chamber at 25 ° C for 24 hours. Then, it was left in a greenhouse (20-22 ° C.) for 4 days, the lesion area that appeared in the leaves was measured, the disease index was determined based on the following criteria, and the control value was calculated by the following equation. The results are shown in Table-5.

[0062]

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

[0063]

(Equation 3)

[0064]

[Table 21] Table-5 {Compound No. concentration (ppm) Pest control value (%)} ───────────────────────── 3 500 100 8 500 90 17 500 100 21 21 500 100 22 500 100 24 500 100 31 500 100 32 500 100 40 500 95 43 500 100 52 500 100 55 500 100 100 61 500 100 63 500 100 65 65 500 100 70 500 100 71 500 100 77 500 100 90 500 100 97 500 100 116 500 100 117 500 100 129 500 100

[0065]

[Table 22] Compound No. concentration (ppm) Control value (%) １３２ 132 500 100 ────────────────────── ──────

[0066]

Industrial Applicability The 1-substituted-pyrazole-3-carboxamide derivative of the present invention has an excellent control effect on various plant pathogens and is useful as an agricultural and horticultural fungicide.

Claims (9)

[Claims] 1. A compound represented by the following general formula (I) (Where A is Wherein R ¹ is a C ₁ -C ₄ alkyl group or C ₁ -C 4
_And R ² , R ³ , R ⁴ , R ⁶ , R
⁷ and R ⁸ are each independently a hydrogen atom, a halogen atom, a C ₁ -C ₅ alkyl group, a trifluoromethyl group,
Nitro group, cyano group, C ₁ -C ₄ alkoxy group, C ₁
Haloalkoxy groups ~C _4, C ₂ ~C ₅ alkoxycarbonyl group, an alkylcarbamoyl group of C ₂ -C _5, C
₁ -C ₄ alkylthio group, C ₁ -C ₄ alkylsulfinyl group, an alkylsulfonyl group having C ₁ -C _4, an amino group, an alkylamino group of C ₁ -C _4, a dialkylamino group of C ₂ -C ₄ A C ₂ -C ₅ alkylcarbonylamino group, a C ₂ -C ₅ alkoxycarbonylamino group,
C ₁ -C showed good phenoxy group which may have a alkylsulfonylamino group or substituent of _4, X is a halogen atom, Y represents an oxygen atom or a sulfur atom, R ⁵
Amino group, an alkylamino group of C ₁ -C ₅ is, C ₂ -C
₄ , dialkylamino group, pyrrolidinyl group, morpholino group, 2,6-dimethylmorpholino group, allylamino group,
Shown propargylamino group, a methoxy group, a methoxy propyl group, a 2,2,2-trifluoroethyl group, cyanomethyl group, an alkyl hydrazino group C ₁ -C _4, a Ariruhidorajino group. However, when R ¹ is a methoxy group and R ⁵ is an alkylamino group, the alkylamino group has 2 to 5 carbon atoms. A) -substituted-pyrazole-3-carboxamide derivative represented by the formula: 2. The compound of the formula (I) wherein R ¹ is C ₁ -C
_2. The 1-substituted-pyrazole-3-carboxamide derivative according to claim 1, which is an alkyl group or an alkoxy group. 3. The 1-substituted-pyrazole-3-carboxamide derivative according to claim 1, wherein R ¹ in the general formula (I) is a methoxy group. 4. R in the general formula (I)^Two, R^Threeand
R^FourOne of or R ⁶, R⁷And R⁸One of the halo
Gen atom, C₁~ C_FiveAlkyl group, trifluoromethyl
Group, cyano group, C₁~ C_FourAn alkoxy group of C₁~ C
_FourAnd a pyrazole ring
A substituent that is substituted at the para-position of the bond with
Is a hydrogen atom.
1-substituted-pyrazole-3-carboxy according to any of
Samide derivatives. 5. R ⁵ in the general formula (I) is C ₂ -C
_4. An alkylamino group of claim 4.
5. The 1-substituted-pyrazole-3-carboxamide derivative according to any one of claims 1 to 4. 6. The 1-substituted-pyrazole-3-carboxamide derivative according to claim 5, wherein R ⁵ in the general formula (I) is an n-propylamino group. 7. The 1-substituted-pyrazole-3-carboxamide derivative according to claim 1, wherein X in the general formula (I) is a chlorine atom or a bromine atom. 8. The 1-substituted-pyrazole-3-carboxamide derivative according to claim 1, wherein Y in the general formula (I) is an oxygen atom. 9. A fungicide for agricultural and horticultural use, comprising the 1-substituted-pyrazole-3-carboxamide derivative according to any one of claims 1 to 8 as an active ingredient.