JPH09278775A - Pyrazole compound and insecticide, acaricide and germicide containing the same as active ingredient - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a new pyrazole compound, having excellent controlling effects on various plant pathogenic fungi, insect pests and mites and high safety and useful as a germicide, an insecticide and an acaricide for agricultural and horticultural uses. SOLUTION: This new pyrazole compound is represented by formula I [R<1> is H, a 1-4C (halo) alkyl or phenyl; R<2> is H, halogen or a 1-4C alkyl; R<1> and R<2> may mutually be bonded to form a (substituted) 5-membered ring saturated hydrocarbon group represented by formula II; R is a 1-4C (halo) alkyl, a halogen, a 1-4C (halo) alkoxy, nitro, cyano, phenyl or a 1-4C alkylthio], e.g. N-[6-(3- trifluoromethylphenoxy)-3-pyridylmethyl]-1,3,4-trimethyl-5-pyrazolecar boxamide. The compound represented by formula I is obtained by reacting a compound represented by formula III (Z is Cl, Br, OH, etc.) with a compound represented by formula IV.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a novel pyrazole compound, and an insecticidal, acaricidal and fungicidal agent for agricultural and horticultural use containing the pyrazole compound as an active ingredient.

[0002]

2. Description of the Related Art Conventionally, in the field of agriculture and horticulture, various fungicides and insecticides have been developed and put into practical use for the purpose of controlling various pests and diseases. However, conventionally used agricultural and horticultural fungicides and insecticides are not always satisfactory in terms of bactericidal / insecticidal effect, bactericidal / insecticidal spectrum, residual effect and the like. Moreover, it cannot be said that the demands such as the number of times of application and the amount of applied drug have 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.

Although there are pesticides (eg, dithiocarbamate-based and phthalimide-based pesticides) for which pathogenic bacteria and pests have not yet acquired resistance, these generally have a large amount of application and the number of times they are applied, and from the viewpoint of environmental pollution, etc. 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. As for acaricides, it is expected to develop a highly safe acaricide which shows an excellent control effect against acaria which has been conventionally resistant to general-purpose acaricides. On the other hand, Japanese Patent Application Laid-Open No. 2-62876 discloses an N- (phenoxypyridylmethyl) pyrazolecarboxamide compound and teaches that this compound has insecticidal, acaricidal and bactericidal activities.

[0005]

However, in the above publications, most of the compounds having a substituent at the 4-position as a substituent of the phenoxy moiety, and those having a substituent at the 3-position are 3,
Only one 4-disubstituted compound is disclosed.
The object of the present invention is to show a high control effect against various pathogenic bacteria and pests that are resistant to conventional agricultural and horticultural germicides and acaricides, and useful as an active ingredient of agricultural and horticultural germicides and insecticides. To provide various chemical substances. Another object of the present invention is to have a highly safe agricultural / horticultural sterilization having the above-mentioned characteristics, and having reduced problems such as residual toxicity and environmental pollution.
To provide pesticides. From another point of view, N- [6- (3-substituted phenoxy) -3 having the above-mentioned utility.
It is an object of the present invention to provide a -pyridylmethyl] pyrazolecarboxamide derivative.

[0006]

Means for Solving the Problems As a result of intensive studies to solve the above problems, the present inventors have found that the novel pyrazole compound represented by the formula (I) is a compound having the above characteristics, The present invention has been completed. That is, the present invention provides: General formula (I)

[0007]

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(Wherein R ¹ represents a hydrogen atom, a C ₁ -C ₄ alkyl group, a phenyl group or a C ₁ -C ₄ haloalkyl group, and R ² represents a hydrogen atom, a C ₁ -C ₄ alkyl group. Or a halogen atom, and R ¹ and R ² are bonded to each other to form a saturated hydrocarbon group having a 5-membered ring which may have a substituent.

[0009]

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(However, R ³ may represent a hydrogen atom or a C ₁ -C ₄ alkyl group). R is C ₁
To C ₄ alkyl group, halogen atom, C _{1 to} C ₄ haloalkoxy group, C _{1 to} C ₄ alkoxy group, nitro group,
A cyano group, a C ₁ -C ₄ haloalkyl group, a phenyl group or a C ₁ -C ₄ alkylthio group).

2. An agricultural and horticultural insecticide containing the pyrazole compound according to item 1 as an active ingredient. 3. An acaricide for agricultural and horticultural use, which comprises the pyrazole compound according to item 1 as an active ingredient. 4. An agricultural and horticultural fungicide containing the pyrazole compound according to item 1 as an active ingredient. It is in. The pyrazole compound of the present invention is a novel compound, but the substituent R of the phenoxy group is 4
A compound having a structure similar to that substituted at the position is disclosed in JP-A-2-62876.
No. As will be apparent from the test examples described later, the compounds of the present invention have the same insecticidal, acaricidal, and bactericidal effects as compared with known compounds having a similar structure, and have extremely low toxicity to mice. R
It is unpredictable that this substitution position will increase the safety in this way. Hereinafter, the present invention will be described in detail.

[0012]

DESCRIPTION OF THE PREFERRED EMBODIMENTS

(1) Pyrazole Compound The pyrazole compound of the present invention is a compound represented by the formula (I). In formula (I), R ¹ is a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, n
A C ₁ -C ₄ linear or branched alkyl group such as a butyl group, an isobutyl group, a sec-butyl group, a t-butyl group; a phenyl group; or a trifluoromethyl group. R
² is a hydrogen atom, a methyl group, an ethyl group, an n-propyl group,
Isopropyl group, n-butyl group, isobutyl group, sec
A C ₁ -C ₄ linear or branched alkyl group such as a butyl group or a t-butyl group; or a halogen atom such as a fluorine atom, a chlorine atom or an iodine atom. R ³ is hydrogen atom, methyl group, ethyl group, n-propyl group, isopropyl group, n
A C ₁ -C ₄ linear or branched alkyl group such as a butyl group, an isobutyl group, a sec-butyl group, and a t-butyl group. R is a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-
Butyl group, C ₁ -C ₄ linear or branched alkyl group of a t- butyl group and the like; or a fluorine atom, a chlorine atom, a halogen atom such as an iodine atom; 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 -Hexafluoro-2-
Propoxy group, 3,3,3-trichloropropoxy group,
4-chlorobutoxy group, 4,4,4-trifluorobutoxy group, 3,3,4,4,4 linear or branched chain haloalkoxy group of C ₁ -C _4, such as pentafluoro-butoxy group; methoxy group , Ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, se
C ₁ -C ₄ linear or branched alkoxy group such as c-butoxy group and t-butoxy group; nitro group, cyano 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 linear or branched chain haloalkyl group having C ₁ -C _4, such as pentafluoro-butyl group; a phenyl group; or methylthio group, ethylthio group, n- propylthio group, isopropylthio group, n- butylthio group, isobutylthio, sec- butylthio group, a linear or branched alkylthio group of C ₁ -C _4, such as t- butylthio group . (2) Method for producing the compound The compound of the present invention represented by the above formula (I) can be produced, for example, according to the following reaction scheme.

[0013]

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(In the above formula, R ¹ , R ² and R are as defined in the above formula (I), and Z is a chlorine atom, a bromine atom, a hydroxyl group, a methoxy group, an ethoxy group or a propoxy group.) In the formula (II), when Z represents a chlorine atom or a bromine atom, an aromatic hydrocarbon such as benzene, toluene or xylene; a ketone such as acetone, methyl ethyl ketone or methyl isobutyl ketone; a halogen such as chloroform or methylene chloride. Hydrocarbon; water; esters such as methyl acetate or ethyl acetate; 0 ° C. to 30 ° C. in a polar solvent such as tetrahydrofuran, acetonitrile, dioxane, N, N-dimethylformamide, N-methylpyrrolidone or dimethyl sulfoxide, preferably Can be reacted in the presence of a base at 0 ° C to 5 ° C. As a base,
For example, sodium hydroxide, potassium hydroxide, pyridine, triethylamine or the like can be used.

Further, in the formula (II), when Z is a hydroxyl group, a methoxy group, an ethoxy group or a propoxy group, it is in the absence of a solvent or N, N-dimethylformamide, N-methylpyrrolidone or dimethyl. 150 to 250 ° C. in a high boiling point solvent such as sulfoxide, preferably 200
The reaction can be carried out at ~ 250 ° C. Incidentally, the compound represented by the formula (II) is, for example, Annalen der
Chemie, Justus Liebig's, 53
6,97,1938, and the compound represented by the formula (III) can be produced by, for example, Journal fuel Praktische.
It can be manufactured according to the method described in Chemie, 146, 95, 1936.

(3) Use of the Compound The compound of the present invention represented by the formula (I) has a high bactericidal effect against plant pathogenic fungi such as blast fungus, rust fungus, downy mildew, and is suitable for agricultural and horticultural use. It is useful as an active ingredient of fungicides. Further, the compound of the present invention is a planthopper such as a sedge brown planthopper, a brown planthopper, a brown leafhopper, a leafhopper such as a leafhopper, a leafhopper such as a leafhopper, an aphid such as a green peach aphid; Eyes; Coleoptera such as azuki bean weevils; Diptera such as house flies, Aedes aegypti and Culex pipiens; insects of the order Orthoptera, as well as spider mites,
Since it has a high control activity against eggs and larvae of the mites of the genus Miscanthus, citrus red mite, etc., it is also 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 formula (I) is used as an agricultural / horticultural fungicide, insecticide, and / or acaricide, it may be used alone, but preferably in the art. It is used in the form of a composition produced using a commonly used agricultural chemical auxiliary agent. The form of the agricultural / horticultural germicide, insecticide, and / or acaricide is not particularly limited, and examples thereof include emulsions, wettable powders, powders, flowable agents, fine granules, granules, tablets, oils,
It is preferable to use a form such as a spraying agent or an atomizing agent. One or more of the above compounds can be blended as an active ingredient.

The above-mentioned agricultural and horticultural fungicides, insecticides, and / or
Or, an agricultural chemical auxiliary agent used for producing an acaricide is used for the purpose of, for example, improving the effect of a fungicide for agricultural and horticultural use, an insecticide, and / or an acaricide, stabilizing, and improving dispersibility. You can do it. For example, carrier (diluent), spreading agent,
An emulsifier, a wetting agent, a dispersant, a disintegrating agent, etc. 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, and sulfoxides such as dimethylsulfoxide. Methylnaphthalene, cyclohexane, animal and vegetable oils, fatty acids, etc. can be mentioned. Also,
As a solid carrier, clay, kaolin, talc, diatomaceous earth,
Silica, calcium carbonate, montmorillonite, bentonite, feldspar, quartz, alumina, sawdust, nitrocellulose,
Starch, gum arabic, etc. can be used.

Usual surfactants can be used as the emulsifier and dispersant. For example, anionic surfactants such as higher alcohol sodium sulfate, stearyl trimethyl ammonium chloride, polyoxyethylene alkyl phenyl ether, and lauryl betaine. , Cationic surfactants, nonionic surfactants, zwitterionic surfactants and the like can be used. Further, spreading agents such as polyoxyethylene nonyl phenyl ether and polyoxyethylene lauryl phenyl ether; wetting agents such as dialkyl sulfosuccinate; carboxymethyl cellulose,
Fixing agents such as polyvinyl alcohol; disintegrating agents such as sodium lignin sulfonate and sodium lauryl sulfate can be used.

Agricultural and horticultural fungicides of the present invention, insecticides, and / or
Alternatively, the content of the active ingredient in the acaricide is 0.1 to 9
It may be selected from the range of 9.5%, and may be appropriately determined according to various conditions such as formulation form and application method. For example, in the case of powder, it is about 0.5 to 20% by weight, preferably 1 to 10% by weight, The wettable powder is about 1 to 90% by weight, preferably 10
It is suitable to prepare so that the active ingredient is contained in an amount of about 80 to 80% by weight, and an emulsion is about 1 to 90% by weight, preferably 10 to 40% by weight.

For example, in the case of an emulsion, a solvent and a surfactant may be mixed with the above compound as an active ingredient to prepare an undiluted emulsion, and this undiluted solution is diluted with water to a predetermined concentration when used. Can be applied. In the case of a wettable powder, the above-mentioned compound as an active ingredient, a solid carrier, a surfactant and the like may be mixed to prepare a stock solution, which may be diluted with water to a predetermined concentration before use. In the case of powders, the above-mentioned compound of the active ingredient, solid carrier and the like can be mixed and applied as it is. In the case of granules, the above-mentioned compound of active ingredient, solid carrier, surfactant and the like can be mixed to prepare. It can be manufactured by granulating and applied as it is. However, the method for producing each of the above-mentioned preparation forms is not limited to the above-mentioned one, and can be appropriately selected by those skilled in the art according to the type of active ingredient, the purpose of application and the like.

Agricultural and horticultural fungicides, insecticides, and / or
Alternatively, the acaricide, in addition to the compound of the present invention is an active ingredient, other active ingredients such as other fungicides, insecticides, acaricides, herbicides, insect growth regulators, fertilizers, soil conditioners, etc. You may mix. Agro-horticultural fungicide of the present invention, an insecticide, and / or application method of the acaricide is not particularly limited,
It can be applied by any method such as foliar application, water surface application, soil treatment, seed treatment and the like. For example, in the case of foliar application, 5-1000 ppm, preferably 10-500 pp
A solution having a concentration range of m can be used at an application rate of about 100 to 200 liters per 10 ares. The application rate in the case of application on the surface of water is usually 1 to 10 kg per 10 are in the case of granules containing 5 to 15% of the active ingredient. For soil treatment,
A solution having a concentration range of 5 to 1000 ppm is 1 to 1 m ²
It can be used at an application rate of about 10 liters. In the case of seed treatment, 10 to 1000 ppm per kg of seed weight
About 10 to 100 ml of the solution having the concentration range of can be applied.

[0024]

EXAMPLES The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples as long as the gist thereof is not exceeded. Example 1 N- [6- (3-trifluoromethylphenoxy) -3
Preparation of -pyridylmethyl] -1,3,4-trimethyl-5-pyrazolecarboxamide 7.7 g of 1,3,4-trimethyl-5-pyrazolecarboxylic acid and 12 g of thionyl chloride were heated under reflux for 1 hour.
After the thionyl chloride was distilled off under reduced pressure, the residue was washed with toluene 2
Dissolved in 0 ml. This solution is 5-aminomethyl-2-
(3-trifluoromethylphenoxy) pyridine 13.
Toluene solution 30 of 4 g and 6.1 g of triethylamine
It was added dropwise to the mixture at 0 to 10 ° C. 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 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 described in Table 1 (No. 10)
18.2 g was obtained. The NMR and IR of the above compound were as follows.

¹ H-NMR (CDCl ₃ ) δ ppm:
2.12 (3H, s), 2.18 (3H, s), 4.0
2 (3H, s), 4.60 (2H, d), 6.08 (1
H, bs), 6.98 (1H, d), 7.31 (1H,
d), 7.40 (1H, bs), 7.50 (2H,
m), 7.78 (1H, dd), 8.16 (1H, d) IR (KBr) cm ^-1 : 3270, 1630, 148
0, 1320, 1120, 920, 830 Example 2 According to the method of Example 1, the compounds shown in Table 1 were obtained. In the table, data other than the melting point are the data of the refractive index (* mark).

[0026]

[Table 1]

[0027]

[Table 2]

Compound No. The NMR and IR of 3, 12 and 17 are as follows. Compound No. 3 ¹ H-NMR (CDCl ₃ ) δppm: 2.24 (3
H, s), 4.11 (3H, s), 4.54 (2H,
d), 6.27 (1H, s), 6.37 (1H, b
s), 6.96 (1H, d), 7.31 (1H, d),
7.39 (1H, s), 7.49 (2H, m), 7.7
5 (1H, dd), 8.12 (1H, d) IR (KBr) cm ^-1 : 3320, 2940, 1660

Compound No. 12 ¹ H-NMR (CDCl ₃ ) δppm: 1.22 (3
H, t), 2.62 (2H, q), 4.12 (3H,
s), 4.55 (2H, d), 6.30 (1H, s),
6.33 (1H, bs), 6.97 (1H, d), 7.
32 (1H, d), 7.40 (1H, s), 7.49
(2H, m), 7.75 (1H, dd), 8.13 (1
H, d) IR (KBr) cm ⁻¹ : 3320, 2980, 165
0,1550,1480,1330,1120,920

Compound No. 17 ¹ H-NMR (CDCl ₃ ) δppm: 4.24 (3
H, s), 4.59 (2H, d), 6.38 (1H, b
s), 6.77 (1H, s), 6.98 (1H, d),
7.4 (6H, m), 7.76 (3H, m), 8.18
(1H, s) IR (KBr) cm ^-1 : 3330,2950,166
0,1550,1480,1320,1120,920 Hereinafter, formulation examples of agricultural and horticultural fungicides, insecticides, and / or acaricides containing the compound of the present invention as an active ingredient are shown.
The form of the agricultural and horticultural agent of the present invention is not limited to the following.

Formulation Example 1: Wettable powder 20 parts by weight of the compound of the present invention, 20 parts by weight of Carplex # 80 (white carbon, Shionogi Pharmaceutical Co., Ltd., trade name), ST Kaolin clay (kaolinite, Tsuchiya Kaolin Co., Ltd.) Brand name) 52 parts by weight, Solpol 9047K (anionic surfactant, Toho Chemical Co., Ltd., product name) 5 parts by weight, Lunox P65L (anionic surfactant, Toho Chemical Co., Ltd., product name) 3 parts by weight Then, the mixture was uniformly mixed and pulverized to obtain a wettable powder containing 20% by weight of the active ingredient.

Formulation Example 2: Dust 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,
Shionogi Seiyaku Co., Ltd., 5 parts by weight) were uniformly mixed and pulverized to produce a powder formulation containing 2% by weight of the active ingredient.

Formulation Example 3: Emulsion 20 parts by weight of the compound of the present invention was dissolved in a mixed solvent consisting of 35 parts by weight of xylene and 30 parts by weight of dimethylformamide, and added to Solpol 3005X (nonionic surfactant and anionic surfactant). 20 parts by weight of the active ingredient by adding 15 parts by weight of a mixture of agents, Toho Chemical Co., Ltd., trade name)
Emulsion was obtained.

Formulation Example 4: Flowable Agent 30 parts by weight of the compound of the present invention and Solpol 9047K 5
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-milled with Dynomill (manufactured by Shinmaru Enterprises). Then, 10 parts by weight of a 1% by weight xanthan gum (natural polymer) aqueous solution was added to this slurry mixture, and the mixture was thoroughly mixed and ground to obtain a flowable agent containing 20% by weight of the active ingredient.

Test Example 1: Insecticidal effect on the larvae of the brown planthopper The budded seedlings of rice were set in a glass cylinder (internal diameter: 3 cm × length: 17 cm), and five fourth-instar larvae of the 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).

[0036]

[Table 3] Table 2 ─────────────────────────── Compound No. Concentration (ppm) Insecticidal rate (%) ─────────────────────────── 1 500 100 2 500 500 100 7 500 500 100 8 500 500 100 9 500 100 10 500 100 100 11 500 100 12 500 500 13 13 500 100 18 500 100 ────────────────────────────

Test Example 2: Insecticidal effect against diamondback moth larvae [0039] Cut cabbage leaves (diameter 6 cm) were immersed for 1 minute in a water-diluted solution of the agricultural and horticultural insecticide of the present invention prepared according to the formulation of Formulation Example 1. After immersion, air-dry the plastic cup (7
cm), and 5 third-instar larvae of Plutella xylostella were released in the cup (1 concentration, 2 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).

[0038]

[Table 4] Table 3 ─────────────────────────── Compound No. Concentration (ppm) Insecticidal rate (%) ─────────────────────────── 4 500 100 5 5500 100 7 7 500 500 100 10 500 500 100 11 500 100 12 500 100 100 13 500 100 18 500 100 ────────────────────────────

Test Example 3: Acaricidal effect on adult worms of the genus Acarina 10 female worms of the genus Mite were released on the leaf disk of kidney bean (diameter 3 cm). 3.5 ml of a liquid obtained by diluting the acaricide for agricultural and horticultural use of the present invention prepared in accordance with the formulation of Formulation Example 1 to a predetermined concentration with water was sprayed onto the disc using a rotary spraying tower (manufactured by Mizuho Rika). (1 concentration, 2 repeats). Twenty-four hours after the treatment, the life and death of the adults were examined to determine the acaricidal rate (%). The results are shown in Table 4.

Test Example 4 Acaricidal Effect on the Eggs of Nymphalid Mite Five adult females of Nymphalid mite were released on a leaf disk of kidney bean (diameter 3 cm). The leaf discs were allowed to lay eggs for 20 hours after the release, and then female adults were removed. Formulation example 1
3.5 ml of the acaricide for agricultural and horticultural use of the present invention, which was prepared according to the above formula, was diluted with water to a predetermined concentration, and was sprayed on the above disc using a rotary spraying tower (manufactured by Mizuho Rika) (1 concentration). , 2). Eight days after the treatment, the number of unhatched eggs and the number of hatched larvae were investigated to determine the ovicidal rate (%). The results are shown in Table 4.

[0041]

[Table 5] Table 4 ───────────────────────────────── Compound No. Concentration (ppm) Acaricidal rate (%) Egg killing rate (%) ────────────────────────────────── 2 500 100 100 12 500 500 100 100 ──────────────────────────────────

Test Example 5: Bactericidal effect on rice blast 10 pots of rice (variety: Akinishi) 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.

[0043]

[Equation 1]

[0044]

[Table 6] Table 5 ─────────────────────────── Compound No. Concentration (ppm) Control value (%) ─────────────────────────── 3 250 100 9 9 250 910 10 250 250 89 11 250 250 85 12 250 100 13 250 87 ────────────────────────────

Test Example 6: Bactericidal effect against tomato epidemic disease In a resin pot having a diameter of 6 cm, 3 strains of rice (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 to 22 ° C.) for 4 days, the number of lesions appearing in the leaves was measured and shown by a disease index, and the control value was calculated by the following formula. Table 6 shows the results. n _x : the number of tomato leaves having the disease index of X per pot

[0046]

[Equation 2]

[0047]

(Equation 3)

[0048]

[Table 7] Table 6 ─────────────────────────── Compound No. Concentration (ppm) Control value (%) ─────────────────────────── 3 250 100 4 4 250 94 5 250 250 100 6 6 250 911 7 250 95 8 250 100 100 9 250 100 100 10 250 100 11 250 250 92 12 250 250 89 13 13 250 85 85 18 250 100 100 ────────────────────────────

Test Example 7: Single-dose test example by forced oral administration in mice No. Acute toxicity (oral) in mice was examined using 8, 10, and 13. The following compounds (IV), (V) and (VI) described in JP-A-2-62876 were similarly tested as control compounds.

[0050]

[Chemical 6]

0.5% CMC-Na aqueous solution (compound N
o. 8 or 10) or 10% of 0.5% tragacanth aqueous solution (Compound No. 13, (IV), (V) and (VI))
Each compound (30 mg) was suspended in a CD-1 mouse male (6
10-week-old, Charles River Co., Ltd.)
The adjusted solution was forcibly orally administered so that the amount became ml (5 /
group). The number of mice that died 7 days after administration was investigated to determine the mortality rate. Table 7 shows the results.

[0052]

[Table 8] Table 7 ──────────────────────────── Compound No. Dose (mg / kg) Mortality rate (%) ──────────────────────────── 8 30 0 10 30 30 13 13 30 0 (IV ) 30 100 (V) 30 100 (VI) 30 100 ─────────────────────────────

[0053]

INDUSTRIAL APPLICABILITY The pyrazole compound of the present invention has an extremely excellent control effect against various plant pathogenic fungi, pests and mites, and is highly safe. The pyrazole compound of the present invention is useful as an agricultural / horticultural fungicide, an insecticide, and an acaricide.

 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Sanae Koike 1000 Kamoshida-cho, Aoba-ku, Yokohama-shi, Kanagawa Mitsubishi Chemical Corporation Yokohama Research Institute (72) Nobuo Okumura 1000 Kamoshida-cho, Aoba-ku, Yokohama-shi, Kanagawa Address: Yokohama Research Institute, Mitsubishi Chemical Corporation

Claims (5)

[Claims] 1. A compound of the general formula (I) (In the formula, R ¹ represents a hydrogen atom, a C _{1 to} C ₄ alkyl group, a phenyl group or a C _{1 to} C ₄ haloalkyl group, and R ²
Is a hydrogen atom, a C ₁ -C ₄ alkyl group or a halogen atom, and R ¹ and R ² are a 5-membered saturated hydrocarbon group which may be bonded to each other to have a substituent. (However, R ³ may represent a hydrogen atom or a C ₁ -C ₄ alkyl group). R is a C ₁ -C ₄ alkyl group, a halogen atom, a C ₁ -C ₄ haloalkoxy group, a C ₁ -C ₄ alkoxy group, a nitro group, a cyano group,
Haloalkyl group C ₁ -C _4, a phenyl group or a C ₁ -C
₄ represents an alkylthio group of ₄ ). 2. In the general formula (I) according to claim 1, R is a C ₁ -C ₄ alkyl group, a halogen atom, or C ₁
To C ₄ haloalkoxy groups or C _{1 to} C ₄ haloalkyl groups, pyrazole compounds. 3. An agricultural and horticultural insecticide containing the pyrazole compound according to claim 1 as an active ingredient. 4. An agricultural and horticultural acaricide containing the pyrazole compound according to claim 1 as an active ingredient. 5. An agricultural and horticultural fungicide containing the pyrazole compound according to claim 1 as an active ingredient.