JPH1053583A - Pyrazole compound and antimicrobial, insecticidal and acaricidal agent containing the same as active ingredient - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject new compound having high control effects against various kinds of pathogenic microbes, insect pests, etc., exhibiting resistance against conventional fungicides for agriculture and horticulture, etc., and useful as an active ingredient for highly safe fungicides, etc., reduced in residual toxicity, environmental pollutions exc. SOLUTION: A pyrazole compound of formula I [R<1> , R<2> are each OH, a 1-4C alkoxy, etc.; R<3> is H or acetyl; R is a 1-4C alkyl, (substituted) phenyl, etc.], e.g. N-[6-(4-trifluoromethylphenoxy)-3-phridylmethyl]-4-methoxy-1,3- dimethyl-5-pyrazole caroxamide. The compound of formula I is obtained by reacting a compound of formula II (Z is chlorine, bromine) in the presence of a base (e.g. NaOH) in an aromatic hydrocarbon such as benzene or in a polar solvent such as a ketone or water at 0-30 deg.C. The compound of formula I is contained as an active ingredient in an amount of 0.1-99.5wt.% in a fungicide for agriculture and horticulture, etc.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a novel pyrazole compound and a fungicide and acaricide for agricultural and horticultural use containing the pyrazole compound as an active ingredient.

[0002]

2. Description of the Related Art In the field of agriculture and horticulture, various fungicides and insecticides for controlling various pests have been developed and put to practical use. However, conventionally used agricultural and horticultural fungicides and insecticides for agricultural and horticultural use are not always satisfactory in terms of the fungicidal and insecticidal effects, the fungicidal and insecticidal spectrum and the 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.

In addition, the emergence of pathogenic bacteria and pests that have acquired resistance to conventional general-purpose 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,
Various pathogens and pests that have acquired resistance to dicarboximide, phenylamide, and organophosphorus pesticides have emerged in various places, and it has become difficult year by year to control various pests caused by these pathogens and pests. ing.

Further, there are pesticides such as dithiocarbamate-based or phthalimide-based pesticides, for which pathogenic bacteria and pests have not yet acquired resistance. Is not preferred. Therefore, a new fungicide and insecticide that shows a sufficient control effect even at low doses against various pathogens and pests that have acquired resistance to conventional general-purpose agricultural and horticultural fungicides and insecticides, and that has little adverse effect on the environment The development of is eagerly awaited.

[0005] In addition, with respect to acaricides, the development of highly safe acaricides that exhibit an excellent control effect on mites that are resistant to conventional acaricides is also expected. On the other hand, Japanese Patent Application Laid-Open No. 2-62876 or Japanese Patent Application No.
-083587 has N- (phenoxypyridylmethyl)
Pyrazole carboxamide compounds are disclosed, which teach that the compounds have insecticidal, acaricidal and fungicidal activity. However, although this publication discloses a compound having an alkyl group or a halogen atom as a substituent at the 3- or 4-position of the pyrazole ring, etc. Not listed. In addition, JP-A-2-264760 and JP-A-7-173139 disclose a pyrazole ring having 3 or 4 rings.
A pyrazolecarboxamide compound having an alkoxy group as a substituent at the position is disclosed.
It is taught to have acaricidal and fungicidal activity. However, this publication states that N-substituted
No mention is made of the (phenoxypyridylmethyl) group.

[0006]

DISCLOSURE OF THE INVENTION The present invention shows a high control effect on various pathogens, pests and mites which are resistant to conventional agricultural and horticultural fungicides, insecticides and acaricides. It is an object of the present invention to provide a chemical substance useful as an active ingredient of fungicides, insecticides and acaricides. Also,
Another object of the present invention is to provide a highly safe fungicide for agricultural and horticultural use having the above-described features and reduced problems such as residual toxicity and environmental pollution, as an active ingredient of an insecticide and an acaricide. It is to provide useful chemical substances. From another viewpoint, it is an object of the present invention to provide an N- [6-phenoxy-3-pyridylmethyl] pyrazolecarboxamide derivative having the above utility.

[0007]

The present inventors have made intensive efforts to solve the above-mentioned problems, and as a result, have found that a novel pyrazole compound represented by the following formula is a compound having the above characteristics. Was completed. That is, the present invention relates to the following general formula (I)

[0008]

Embedded image

[In the above formula, ^one of R ¹ and R ² is a hydroxyl group, a C ₁ -C ₄ alkoxy group, an acetoxy group, a C ₁ -C ₄
A haloalkoxy group, a C ₁ -C ₄ alkoxyalkoxy group or a benzyloxy group, and the other is a hydrogen atom,
An alkyl group or a halogen atom ₁ -C _4. R ³ represents a hydrogen atom or an acetyl group, R represents a substituted with a substituent selected alkyl group of C ₁ -C _4, haloalkoxy group C ₁ -C _4, haloalkyl group or a halogen atom C ₁ -C ₄ And a bactericidal, insecticidal and acaricide for agricultural and horticultural use containing this compound as an active ingredient.

Hereinafter, the present invention will be described in detail.

[0011]

BEST MODE FOR CARRYING OUT THE INVENTION ^One of the substituents R ¹ and R ² of the compound of the present invention represented by the general formula (I) is a hydroxyl group; a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, A C ₁ -C ₄ linear or branched alkoxy group such as -butoxy group, isobutoxy group, sec-butoxy group, t-butoxy group; acetoxy group; difluoromethoxy group, trifluoromethoxy 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-trifluoropropoxy group, 2,2,3,3-
Tetrafluoropropoxy group, 2,2,3,3,3-pentafluoropropoxy group, 2,2-dichloro-3,
3,3-trifluoropropoxy group, 1,3-difluoro-2-propoxy group, 1,1,1,3,3,3-hexafluoro-2-propoxy group, 3,3,3-trichloropropoxy group, 4-chlorobutoxy group, 4,4,4-
Trifluoride Rob butoxy group, 3,3,4,4,4 straight or branched chain haloalkoxy group of C ₁ -C _4, such as pentafluoro-butoxy group; methoxymethoxy, ethoxymethoxy, n- propoxy methoxy, ethoxy ethoxy and the like C
A linear or branched alkoxyalkoxy group of ₁ to ₄ carbon atoms;
Or a benzyloxy group, and the other is a hydrogen atom; a methyl group, an ethyl group, an n-propyl group, an isopropyl group,
n-butyl group, isobutyl group, sec-butyl group, t-
A C ₁ -C ₄ linear or branched alkyl group such as a butyl group; or a halogen atom such as a fluorine atom, a chlorine atom or an iodine atom. R ³ represents a hydrogen atom; or an acetyl group. R represents a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-
Butyl group, a linear or branched alkyl group of C ₁ -C ₄ in a t- butyl group and the like; a difluoromethoxy group, a trifluoromethoxy 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-trifluoropropoxy group, 2,2,3,3-tetrafluoropropoxy group, 2,2,3 3,3-pentafluoropropoxy group, 2,2-dichloro-3,3,3-trifluoropropoxy group, 1,3-difluoro-2-propoxy group, 1,1,1,3,3,3-hexa Fluoro-2-propoxy group, 3,3,3-trichloropropoxy group, 4
- chlorobutoxy group, 4,4,4-trifluorobutoxy group, 3,3,4,4,4 straight or branched chain haloalkoxy group of C ₁ -C _4, such as pentafluoro-butoxy group;
Difluoromethyl group, trifluoromethyl group, 2-fluoroethyl group, 2-chloroethyl group, 2,2,2-trifluoroethyl group, 2,2,2-trichloroethyl group,
3-chloropropyl group, 3-bromopropyl group, 3,
3,3-trifluoropropyl group, 2,2,3,3-tetrafluoropropyl group, 2,2,3,3,3-pentafluoropropyl group, 2,2-dichloro-3,3,3-
Trifluoropropyl group, 1,3-difluoro-2-propyl group, 1,1,1,3,3,3-hexafluoro-
2-propyl group, 3,3,3-trichloropropyl group,
4-chlorobutyl group, 4,4,4-trifluoro butyl group, 3,3,4,4,4 straight or branched chain haloalkyl group having C ₁ -C _4, such as pentafluoro-butyl group; or a fluorine atom, And a phenyl group which may be substituted with a substituent such as a halogen atom such as a chlorine atom and an iodine atom.

The compound of the present invention represented by the above general formula (I) can be produced, for example, according to the following reaction formula.

[0013]

Embedded image

[Wherein R ¹ , R ² , R ³ and R are as defined in the above formula (I), Z is a chlorine atom,
Represents a bromine atom, a hydroxyl group, a methoxy group, an ethoxy group or a propoxy group] In the above general formula (II), when Z represents a chlorine atom or a bromine atom, the solvent is an aromatic hydrocarbon 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 tetrahydrofuran, acetonitrile, dioxane, N, N-dimethylformamide; The reaction can be carried out using a polar solvent such as N-methylpyrrolidone or dimethyl sulfoxide at 0 ° C to 30 ° C, preferably 0 ° C to 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, in the absence of a solvent, or in the presence of N, N-dimethylformamide, N-methylpyrrolidone Alternatively, the reaction can be carried out in a high boiling point solvent such as dimethyl sulfoxide at 150 to 250 ° C, preferably 200 to 250 ° C.
The compound represented by the general formula (II) is, for example, T
etrahedronLetters, 1591, (1
971), and the compound represented by the general formula (III) is, for example, Journal fur Praktische
Chemie, 146, 95, (1936).

The compound of the present invention represented by the general formula (I)
It has a high bactericidal effect against plant pathogenic fungi such as blast fungus, rust fungus and downy mildew fungus, and is useful as an active ingredient of a fungicide for agricultural and horticultural use. Further, the compounds of the present invention are planthoppers such as brown planthoppers, brown planthoppers, brown planthoppers, leafhoppers such as leafhoppers and leafhoppers,
Hemiptera such as aphids such as peach aphids; Lepidoptera such as Spodoptera litura;
In addition, it has high control activity against eggs and larvae of the order Acarina, such as the red mite spider mite, the red mite spider mites, and the red mites, and is therefore useful as an active ingredient of agricultural and horticultural insecticides and acaricides. However, the phytopathogenic fungi, insects and mites 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, an insecticide and an acaricide for agricultural and horticultural use, it may be used alone, but is preferably used in the art. It is preferably used as a composition to which a pesticide auxiliary is added. The dosage forms of the agricultural and horticultural fungicides, insecticides and acaricides are not particularly limited. For example, emulsions, wettable powders, powders, flowables, fine granules, granules, tablets, oils, sprays, aerosols, etc. It is preferable to take the form of One or more of the above compounds can be blended as an active ingredient.

The agricultural pesticide adjuvants used for producing the agricultural and horticultural fungicides, insecticides and acaricides include, for example,
Improve the effects of agricultural and horticultural fungicides, insecticides and acaricides,
It can be used for the purpose of stabilization and improvement of dispersibility. For example, carriers (diluents), spreading agents, emulsifiers, wetting agents, dispersants, disintegrants, 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; Examples include cyclohexane; animal and vegetable oils; and fatty acids. Further, as a solid carrier, clay, kaolin, talc, diatomaceous earth, silica, calcium carbonate, montmorillonite, bentonite, feldspar,
Quartz, alumina, sawdust, nitrocellulose, starch,
Gum arabic or the like can be used. 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 agricultural and horticultural fungicide, insecticide and acaricide of the present invention is 0.1 to 99.5%.
And may be appropriately determined in accordance with various conditions such as the form of the preparation, the method of application, and the like.
5 to 20% by weight, preferably 1 to 10% by weight, about 1 to 90% by weight, preferably 10 to 80% by weight for wettable powder, and about 1 to 90% by weight, preferably 10 to 10% by weight for emulsion.
It is preferred to manufacture such that they contain ４０40% by weight of active ingredient.

For example, in the case of an emulsion, an emulsion of a stock solution can be prepared by mixing a solvent and a surfactant with the above-mentioned compound as an active ingredient, and the stock solution is diluted with water to a predetermined concentration when used. And can be applied. In the case of a wettable powder, a stock solution is prepared by mixing the above-mentioned compound of the active ingredient, a solid carrier, a surfactant and the like, and this stock solution can be 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, and in the case of granules, the compound of the active ingredient, the solid carrier and the surfactant can be mixed and granulated. It can be manufactured and 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 fungicides, insecticides and acaricides for agricultural and horticultural use of the present invention include, in addition to the compound of the present invention, other fungicides, insecticides, acaricides, herbicides and insect growth regulators. Agent,
An optional active ingredient such as a fertilizer or a soil conditioner may be added. The method of applying the fungicide for agricultural and horticultural use, the insecticide and the acaricide of the present invention is not particularly limited, and it can be applied by any method such as foliage application, water application, soil treatment, seed treatment and the like. For example, in the case of foliage application, 5 to 100
A solution having a concentration range of 0 ppm, preferably 10 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 rate is usually 1 to 10 kg per 10 ares for granules containing 5 to 15% of the active ingredient. 5-1000p for soil treatment
A solution having a concentration range of pm can be used at an application rate of about 1 to ¹⁰ L per m ² . In the case of seed treatment, about 10 to 100 ml of a solution in a concentration range of 10 to 1000 ppm per 1 kg of seed weight can be applied. Hereinafter, the present invention will be described more specifically with reference to Examples.
The scope of the present invention is not limited to the following examples.

[0022]

【Example】

<Example 1> N- [6- (4-trifluoromethylphenoxy) -3-pyridylmethyl] -4-methoxy-
Production of 1,3-dimethyl-5-pyrazolecarboxamide 1.7 g of 4-methoxy-1,3-dimethyl-5-pyrazolecarboxylic acid and 5 g of thionyl chloride were heated under reflux for 1 hour. After the thionyl chloride was distilled off under reduced pressure, the residue was dissolved in 20 ml of toluene. This solution was treated with 5-aminomethyl-
The solution was added dropwise at 0 to 10 ° C. to 30 ml of a toluene solution of 2.7 g of 2- (4-trifluoromethylphenoxy) pyridine and 1.2 g of triethylamine. Room temperature after dropping
After stirring for an hour, the reaction solution was poured into ice water and extracted with toluene. The toluene layer was washed sequentially with an aqueous sodium hydrogen carbonate solution, water, and saturated saline. After drying over anhydrous sodium sulfate,
The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography, and the compound (No.
8) 3.8 g were obtained.

The NMR and IR of the above compound were as follows. ¹ H-NMR (CDCl ₃ ) δ ppm: 2.29 (3H,
s), 3.84 (3H, s), 4.10 (3H, s),
4.58 (2H, d), 6.98 (1H, d), 7.2
3 (2H, d), 7.56 (1H, b), 7.65 (2
H, d), 7.76 (1H, dd), 8.17 (1H,
d) IR (KBr) cm ^-1 : 3380, 1660, 160
0, 1480, 1320, 1280, 1160, 112
0,1060

<Embodiment 2> According to the method of Embodiment 1, Table 1
Was obtained. In the table, the numbers marked with * represent the refractive index.

[0025]

[Table 1]

[0026]

[Table 2]

Compound No. The NMR data of No. 1 was as follows. ¹ H-NMR (CDCl ₃ ) δ ppm: 2.03 (3H,
s), 4.06 (3H, s), 4.55 (2H, d),
6.92 (1H, d), 7.27 (1H, d), 7.3
5 (1H, s), 7.45 (2H, m), 7.75 (2
H, m), 8.08 (1H, d), 8.50 (1H,
s) Formulation examples of agricultural and horticultural fungicides, insecticides and acaricides containing the compound of the present invention as an active ingredient are shown below, but the form of the agricultural and horticultural agent of the present invention is limited to the following. There is no.

<Formulation Example 1> Wetting agent 20 parts by weight of the compound of the present invention, 20 parts by weight of carplex # 80 (white carbon, Shionogi & Co., Ltd., trade name), ST kaolin clay (Kaolinite, Tsuchiya Kaolin) 52 parts by weight), 5 parts by weight of Solpol 9047K (anionic surfactant, Toho Chemical Co., trade name), 3 parts by weight of Lunox P65L (anionic surfactant, Toho Chemical Co., Ltd.) The mixture was mixed and uniformly mixed and pulverized to obtain a wettable powder containing 20% by weight of the active ingredient.

<Formulation Example 2> Powder 2 parts by weight of the compound of the present invention, clay (manufactured by Nippon Talc) 9
3 parts by weight, carplex # 80 (white carbon,
5 parts by weight of Shionogi & Co., Ltd. (trade name) were uniformly mixed and pulverized to produce a powder containing 2% by weight of the active ingredient.

<Formulation Example 3> Emulsion 20 parts by weight of the compound of the present invention are dissolved in a mixed solvent consisting of 35 parts by weight of xylene and 30 parts by weight of dimethylformamide, and dissolved in Solpol 3005X (a nonionic surfactant and an anionic interface). Addition of a mixture of activators, Toho Chemical Co., Ltd., 15 parts by weight, and 20% by weight of active ingredient
Emulsion was obtained.

<Formulation Example 4> Flowable agent 30 parts by weight of the compound of the present invention, Solpol 9047K5
Parts by weight, 3 parts by weight of Sorbon T-20 (nonionic surfactant, Toho Chemical Co., Ltd., trade name), 8 parts by weight of ethylene glycol and 44 parts by weight of water are wet-pulverized with a Dynomill (manufactured by Shinmaru Enterprises). Then, 10 parts by weight of a 1% by weight aqueous solution of xanthan gum (natural polymer) was added to the slurry-like mixture, and the mixture was thoroughly mixed and pulverized.
By weight, a fullable agent was obtained.

<Test Example 1> Insecticidal effect of brown planthopper on larvae Rice seedlings were set on a glass cylinder (inner diameter 3 cm x length 17 cm), and five fourth-stage larvae of brown planthopper were released. 0.5 ml of a water dilution of the agricultural and horticultural insecticide of the present invention produced according to the formulation of Formulation Example 3 was sprayed on the above-mentioned glass cylinder using a spray tower (manufactured by Mizuho Rika) (1 concentration, 2 repetitions). Five days after the treatment, the larvae were examined for their life and death and agony, and the killing rate (%) was determined assuming that the agony worms were killed by 頭. The results are shown in Table 2 (the compound numbers in the table correspond to Table 1).

[0033]

[Table 3]

<Test Example 2> Insecticidal effect on Japanese larva of Japanese moth Cabbage cut leaves (6 cm in diameter) were immersed in a water dilution of the agricultural and horticultural insecticide of the present invention produced according to the formulation of Preparation Example 1 for 1 minute. After immersion, air-dry and put in a plastic cup (7 cm inside diameter).
The head was released (one concentration, two repetitions). After 4 days from the release, the larvae were examined for viability and agony, and the killing rate (%) was determined by assuming that the agony insects were 死 dead. The results are shown in Table 3 (in the following table, the compound numbers correspond to Table 1).

[0035]

[Table 4]

<Test Example 3> Acaricidal effect on adult adults of the spider mite Ten adult female spider mites were released on leaf disks (3 cm in diameter) of kidney beans. 3.5 ml of a solution prepared by diluting the acaricide for agricultural and horticultural use of the present invention prepared according to the formulation of Formulation Example 1 to a predetermined concentration with water was sprayed on the disk using a rotary spraying tower (manufactured by Mizuho Rika). (1 concentration, 2 replicates). Twenty-four hours after the treatment, the life and death of the adults were examined to determine the acaricidal rate (%). Table 4 shows the results.

<Test Example 4> Acaricidal effect on spider mite eggs Eggs of five adult spider mites were released on leaf disks (3 cm in diameter) of kidney beans. The eggs were laid on a leaf disk for 20 hours after the release, and then the female adults were removed. Formulation Example 1
3.5 ml of a solution prepared by diluting the agricultural and horticultural acaricide of the present invention, prepared in accordance with the above formula, with water to a predetermined concentration, was sprayed on the disk using a rotary spraying tower (manufactured by Mizuho Rika) (1 concentration). , 2 repetitions). Eight days after the treatment, the number of unhatched eggs and the number of hatched larvae were examined to determine the ovicidal rate (%). Table 4 shows the results.

[0038]

Table 4 Table 4 化合物 Compound No. Concentration (ppm) Acaricidal rate (%) Egg kill rate (% %) {7 500 100 100 9 9 500 100 100 100 10 500 100 100 100 21 500 100 100 24 500 100 100} ──────────────────────────

Test Example 5 Germicidal 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 for agricultural and horticultural use (wettable powder) of the present invention prepared according to the formulation of Formulation Example 1 is diluted to a predetermined concentration with water, and foliage is sprayed on the rice (3-4 leaf stage) at a rate of 10 ml per pot. did. After the sprayed drug solution was air-dried, the rice blast fungus (Magnaporthe grisea) cultured in oatmeal medium was added to the rice.
Was spray inoculated with a spore suspension (5.0 × 10 ⁵ spores / ml) and kept in a moist chamber at 25 ° C. for 24 hours. Then, it was left in a greenhouse (22 to 25 ° C.) for 7 days, the number of lesions that appeared was measured, and the control value was calculated by the following formula. Table 5 shows the results.

[0040]

(Equation 1)

[0041]

[Table 6]

Test Example 6 Bactericidal Effect on Tomato Blight In a resin pot having a diameter of 6 cm, three rice plants (variety: red cherry) were grown per pot. 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 number of lesions appearing in the leaves was measured, the disease index was used, and the control value was calculated by the following formula. Table 6 shows the results.

[0043] _nx : number of tomato leaves with the disease index x per pot

[0044]

(Equation 2)

[0045]

(Equation 3)

[0046]

[Table 7]

[0047]

Industrial Applicability The pyrazole compound of the present invention has an extremely excellent controlling effect on various plant pathogenic bacteria, pests, and mites. The pyrazole compound of the present invention is useful as an agricultural and horticultural fungicide, insecticide and acaricide.

 ──────────────────────────────────────────────────の Continued on the front page (72) Inventor Hirofumi Tomita 1000 Kamoshita-cho, Aoba-ku, Yokohama-shi, Kanagawa Prefecture Inside Mitsubishi Research Institute Yokohama Research Laboratory (72) Sumitomo Higashino 1000 Kamoshida-cho, Aoba-ku, Yokohama-shi, Kanagawa Mitsubishi Chemical Corporation Yokohama Research Laboratory

Claims (5)

[Claims] 1. A compound represented by the following general formula (I): [In the above formula, ^one of R ¹ and R ² is a hydroxyl group, a C ₁ -C ₄ alkoxy group, an acetoxy group, a C ₁ -C ₄ haloalkoxy group, a C ₁ -C ₄ alkoxyalkoxy group or a benzyloxy group. And a hydrogen atom, a C ₁ -C ₄ alkyl group or a halogen atom. R ³ represents a hydrogen atom or an acetyl group, R represents an alkyl group of C ₁ ~C _4, C ₁ ~
C ₄ haloalkoxy group, C ₁ -C shows a phenyl group which may be substituted with a substituent selected from haloalkyl groups or halogen atoms of _4] pyrazole compound represented. 2. The pyrazole compound according to claim 1, wherein in formula (I), one of R1 and R2 is a C ₁ -C ₄ alkoxy group. 3. A fungicide for agricultural and horticultural use comprising the pyrazole compound according to claim 1 as an active ingredient. 4. An agricultural and horticultural insecticide comprising the pyrazole compound according to claim 1 as an active ingredient. 5. An acaricide for agricultural and horticultural use comprising the pyrazole compound according to claim 1 as an active ingredient.