JP2001172261A - Pyrazolecarboxylic amides, and insecticides and acaricides containing the same as an active ingredient - Google Patents

Abstract

(57) [Summary] [PROBLEMS] Excellent control effect against harmful insects and mites
A novel compound having the formula: SOLUTION: The following general formula (I) Embedded image (Where R¹Is C₁-C_Three Acyclic or cyclic alkyl of
Group, C₁-C_FourAn alkoxy group or trifluoromethyl
Represents a group. R^TwoIs C_Two-C_Five An acyl group of C_Two-C_TenOki
Soacyl group, C_Two-C_Ten An alkoxycarbonyl group,
A phenoxycarbonyl group which may have a substituent,
A benzoyl group which may be present, C_Two-C_Five The alkoxymethy
Group, a pyridylmethyl group which may have a substituent, C_Three-C
₆An alkoxycarbonylmethyl group, ethyloxalyl
Group or a cyanomethyl group. R ^Three Is a hydrogen atom, shear
No group, C₁-C_Four An alkylthio group of C₁-C_FourThe alkyl of
Sulfinyl group, C₁-C_Four Alkylsulfonyl group of C
₁-C_Four Haloalkyl group, nitro group, halogen atom, C
₁-C_FourAn alkyl group of C₁-C_FourAn alkoxy group of C₁-C
_FourHaloalkoxy group or C₁-C_FiveAcylamino group of
Is shown. R^FourIs a hydrogen atom or C₁-C_FourThe alkyl group of
Pyrazolecarboxylic acid amides represented by:

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to novel pyrazolecarboxylic acid amides and insecticides and acaricides containing the pyrazolecarboxylic acid amides as active ingredients.

[0002]

2. Description of the Related Art In the field of agriculture and horticulture, various insecticides for controlling various pests have been developed and put to practical use. However, conventionally used agricultural and horticultural insecticides are not always satisfactory in terms of insecticidal effect, insecticidal spectrum, residual efficacy, and the like. In addition, it cannot be said that the requirements such as the reduction in the number of applications and the amount of applied medicine are satisfied. In addition, the appearance of pests that have acquired resistance to conventional pesticides has also become a problem. For example, vegetables,
In cultivation of fruit trees, flowers, tea, wheat and rice,
Various pesticides of various strains, for example, carbamates, pyrethroids, benzoylureas, organochlorines, and various pests that have acquired resistance to organophosphorus pesticides, have appeared in various places and are caused by these pests. The control of various pests is becoming more difficult year by year. There is a strong need for the development of a novel insecticide that exhibits a sufficient control effect at a low dose even with respect to various pests that have acquired resistance to conventional agricultural and horticultural insecticides, and that has little adverse effect on the environment. As for the acaricide, the development of a highly safe acaricide is also expected, which shows an excellent control effect on mites which are resistant to conventional acaricides.

Many proposals have been made for compounds having insecticidal and acaricidal activity. For example, JP-A-3-6
No. 8560 and JP-A-7-112297 show that N-substituted-N- (phenoxybenzyl) pyrazolecarboxylic amides having a specific substituent have insecticidal activity. Therefore, the pyrazolecarboxylic acid amides described in these publications cannot be sufficiently satisfied as insecticides and acaricides.

[0004]

SUMMARY OF THE INVENTION An object of the present invention is to provide a chemical substance which exhibits a high control effect on various pests which are resistant to conventional insecticides and which is useful as an active ingredient of the insecticide. It is in. Another object of the present invention is to provide a highly safe insecticide having the above characteristics and having reduced problems such as residual toxicity and environmental pollution.

[0005]

The inventors of the present invention have conducted intensive studies to solve the above-mentioned problems, and as a result, a novel pyrazolecarboxylic acid amide having a substituent having 2 or more carbon atoms at the nitrogen atom of the amide bond has been obtained. The present invention has been found to be a compound having the following characteristics: That is, the gist of the present invention is represented by the following general formula (I)

[0006]

Embedded image

(Wherein R ¹ represents a C ₁ -C ₃ acyclic or cyclic alkyl group, a C ₁ -C ₄ alkoxy group or a trifluoromethyl group. R ² represents a C ₂ -C ₅ acyl) Group, C
Oxoacyl groups ₂ -C _10, C ₂ -C ₁₀ alkoxycarbonyl group which may have a substituent phenoxycarbonyl group, an benzoyl group which may have a substituent, an alkoxymethyl group of C ₂ -C ₅ an optionally substituted pyridylmethyl group, alkoxycarbonylmethyl group C ₃ -C _6, showing the Echiruokizariru group or a cyanomethyl group. R ³ is a hydrogen atom, a cyano group, a C ₁ -C ₄ alkylthio group, a C ₁ -C ₄
Alkylsulfinyl group, an alkylsulfonyl group having C ₁ -C _4, haloalkyl group of C ₁ -C _4, nitro group, a halogen atom, an alkyl group of C ₁ -C _4, alkoxy group of C ₁ -C _4, C ₁ -C shows a haloalkoxy group, or an acylamino group of C ₁ -C _{5 4.} R ⁴ represents a hydrogen atom or a C ₁ -C ₄ alkyl group) and an insecticide containing the pyrazole carboxylic acid amide as an active ingredient. As described above, it is already known that N-substituted-N- (phenoxybenzyl) pyrazolecarboxylic acid amides have insecticidal activity, but any of the compounds of the present invention represented by the above-mentioned general formula (I) is known. Not shown. That is, JP-A-3-68560 describes that the 3-position of the pyrazole ring is only a hydrogen atom, a C ₁ -C ₄ alkyl group or a C ₃ -C ₆ cycloalkyl group, and an alkoxy group. There is no description. The compounds of the pyrazole ring 4-position is a hydrogen atom, a nitrogen atom of the amide group compounds formyl group is substituted only (Compound A shown in the test examples described later), C ₂ to the nitrogen atom of the amide group
N-substituted-N- (phenoxybenzyl) pyrazolecarboxylic amides having the above groups are not shown.
In JP-A-7-112972, the 3-position of the pyrazole ring is limited to only a tert-butyl group.

[0008]

BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in detail.
The substituent R of the compound of the present invention represented by the general formula (I)¹ Is
Methyl, ethyl, propyl, isopropyl,
C such as chloropropyl group₁-C_ThreeAcyclic or cyclic al
Kill group: methoxy group, ethoxy group, propoxy group, iso
Propoxy, butoxy, isobutoxy, sec-butoxy
C such as xy group and tert-butoxy group₁-C_FourAn alkoxy group of
Indicates a trifluoromethyl group. R¹ As methyl
Groups, ethyl groups and methoxy groups are preferred. R^Two Is Ase
Butyl, propionyl, butyryl, isobutyryl
Group, cyclopropylcarbonyl group, valeryl group, isobaric group
C such as relyl group, 2-methylbutyryl group and pivaloyl group_Two-
C_FiveAcyl group of 3-oxobutyryl group, 2-methyl-3-o
Xoxovaleryl group, 2-ethyl-3-oxohexanoyl group, 3
-Oxo-2-propylheptanoyl group, 2-isopropyl-5
-Methyl-3-oxohexanoyl group, 2,2,4-trimethyl-5
-C such as -oxovaleryl group_Two-C_Ten, Preferably C _Four-C
_TenOxoacyl group; methoxycarbonyl group, ethoxy
Cicarbonyl group, propoxycarbonyl group, isopropo
Xycarbonyl group, butoxycarbonyl group, isobutoki
Cicarbonyl group, sec-butoxycarbonyl group, tert-butyl
Toxycarbonyl group, 2-ethylhexyloxycarboni
C such as_Two-C_TenAn alkoxycarbonyl group of pheno
Xycarbonyl group, p-chlorophenoxycarbonyl group, etc.
A phenoxycarbonyl group optionally having a substituent;
Having a substituent such as a zoyl group or an o-methoxybenzoyl group
Benzoyl group; methoxymethyl group, ethoxymethyl
Group, propoxymethyl group, isopropoxymethyl group,
Butoxymethyl group, isobutoxymethyl group, sec-butoxy
C such as cimethyl group and tert-butoxymethyl group_Two-C _FiveNo
Lucoxymethyl group; 6-chloro-3-pyridylmethyl group, etc.
Optionally substituted pyridylmethyl group; methoxycal
C such as bonylmethyl group and ethoxycarbonylmethyl group_Three-
C₆An alkoxycarbonylmethyl group; ethyloxali
And a cyanomethyl group. R^TwoAs C_Two-C_Five of
Acyl group, C_Two-C_Ten An oxoacyl group and C_Two-C_Fiveof
Alkoxymethyl groups are preferred.

R ³ is a hydrogen atom; cyano group; C ₁ -C ₄ alkylthio such as methylthio, ethylthio, propylthio, isopropylthio, butylthio, isobutylthio, sec-butylthio, tert-butylthio and the like. Group;
Methylsulfinyl group, ethylsulfinyl group, propyl sulfinyl group, isopropyl sulfinyl group, butyl sulfinyl group, isobutyl sulfinyl group, sec- butyl sulfinyl group, an alkylsulfinyl group having C ₁ -C _4, such as tert- butyl sulfinyl group; methylsulfonyl group C ₁ -C ₄ alkylsulfonyl groups such as, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, butylsulfonyl, isobutylsulfonyl, sec-butylsulfonyl, tert-butylsulfonyl and the like;
A C ₁ -C ₄ haloalkyl group such as a trifluoromethyl group, a difluoromethyl group, a trichloromethyl group, and a pentafluoroethyl group; a nitro group; a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom; A C ₁ -C ₄ alkyl group such as an ethyl group, a propyl group, an isopropyl group and a tert-butyl group; a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, a sec-butoxy group and a tert-butyl group C ₁ -C ₄ alkoxy group such as butoxy group; trifluoromethoxy group, difluoromethoxy group, fluoromethoxy group, trichloromethoxy group, 2-fluoroethoxy group, 2,2,2-trifluoroethoxy group, 2,2 , 3,3,3-pentafluoropropoxy group, 2,2,3,
A C ₁ -C ₄ haloalkoxy group such as a 3-tetrafluoropropoxy group, a 2,2,3,3,4,4,4-heptafluorobutoxy group;
C ₁ -C ₅ acylamino groups such as formylamino, acetylamino, propionylamino, butyrylamino, isobutyrylamino, valerylamino, isovalerylamino, 2-methylbutyrylamino, pivaloylamino and the like Is shown. R ³ is preferably a cyano group, a methylthio group, a trifluoromethyl group or a nitro group, and particularly preferably a cyano group or a methylthio group.

R ⁴ is a hydrogen atom; methyl, ethyl, propyl, isopropyl, butyl, isobutyl,
It represents a C ₁ -C ₄ alkyl group such as a sec-butyl group and a tert-butyl group. R ⁴ is preferably a hydrogen atom. 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.

[0011]

Embedded image

(Wherein R ¹ , R ² , R ³ and R ⁴
Is as defined in the above general formula (I), and Y 1 represents a chlorine atom or a bromine atom. That is, the pyrazolecarboxylic acid amide represented by the general formula (II) and the halide represented by the general formula (III) are reacted in the presence or absence of a base, preferably using a solvent, at -10 to 150 ° C. To react. The solvent is not particularly limited as long as it does not directly participate in the reaction, and examples thereof include aromatic hydrocarbons such as benzene, toluene, and xylene; ketones such as acetone, methyl ethyl ketone, and methyl isobutyl ketone; halogenation such as chloroform and dichloromethane. Hydrocarbons; water; esters such as ethyl acetate and methyl acetate; and polar solvents such as tetrahydrofuran, acetonitrile, dioxane, N, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide and pyridine. Examples of the base include alkali metal hydrides such as sodium hydride; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate;
Inorganic salts; amines such as pyridine and triethylamine, and the like. When R ² represents a C ₂ -C ₅ acyl group, it can be produced, for example, according to the following reaction.

[0013]

Embedded image

(Wherein R ¹ , R ³ and R ⁴ are as defined in the above formula (I), and R ² represents a C ₂ -C ₅ acyl group). The pyrazolecarboxylic acid amide represented by II) is reacted with an acid anhydride represented by the general formula (VI) at 0 to 150 ° C. in the presence or absence of an acid catalyst, in the presence or absence of a solvent. . The solvent is not particularly limited as long as it does not directly participate in the present reaction, and examples thereof include the above-mentioned solvents. The acid catalyst is not particularly limited, and examples thereof include sulfonic acids such as benzenesulfonic acid, p-toluenesulfonic acid, methanesulfonic acid, ethanesulfonic acid, and trifluoromethanesulfonic acid; and inorganic acids such as sulfuric acid, hydrochloric acid, and phosphoric acid. Can be. After the reaction, in order to isolate the target compound represented by the general formula (I), when a solvent that dissolves in water is used, the solvent is distilled off under reduced pressure, and water is added. Aromatic hydrocarbons such as benzene, toluene, and xylene insoluble in water; halogenated hydrocarbons such as chloroform and dichloromethane; extracted with esters such as ethyl acetate, washed with saturated saline, and then dried over anhydrous sodium sulfate, anhydrous magnesium sulfate, etc. Dried with a desiccant,
The solvent may be distilled off under reduced pressure. When a solvent insoluble in water is used, water is added to the reaction mixture, and the mixture is separated. The organic layer is washed with saturated saline, dried over a drying agent such as anhydrous sodium sulfate, anhydrous magnesium sulfate, and the like. The solvent may be distilled off. The residue obtained after distilling off the solvent is purified by recrystallization, suspension washing, column chromatography or the like to obtain the desired compound represented by the general formula (I). The compound represented by the general formula (II) is described in, for example, JP-A-64-35763.
Can be synthesized by the method described in Japanese Patent Application Laid-Open Publication No. H11-260, 1988.

The compound of the present invention represented by the formula (I) has a controlling activity against various insects and mites. In particular, the compounds of the present invention include Lepidoptera, such as Spodoptera litura, Konaga, Kanokokakumamonamaki, Kobumemeiga, and Nikamechu;
Planthoppers, such as brown planthoppers and brown planthoppers, leafhoppers, such as leafhoppers and leafhoppers,
Aphids such as peach aphid and cotton aphid; whiteflies such as whiteflies; It has a high control effect on larvae and adults of insects of the order Orthoptera, such as cockroaches, as well as eggs, larvae and adults, of the order of mites, such as spider mite, mandarin red mite, citrus red mite, and terrestrial mite. It is useful as an active ingredient of agricultural and horticultural insecticides and acaricides. However, 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 insecticide or acaricide for agricultural and horticultural use, it may be used alone, but is preferably produced using an agricultural chemical adjuvant commonly used in the art. It is used in the form of a prepared composition. Agricultural and horticultural insecticides, forms of miticides are not particularly limited, for example, emulsions, wettable powders, aqueous solvents, powders,
It is suitable to be in the form of flowables, fine granules, granules, tablets, oils, sprays, aerosols and the like. One or more of the compounds of the present invention can be incorporated as an active ingredient.

Agrochemical auxiliaries used for producing agricultural and horticultural insecticides and acaricides are intended to improve the effects, stabilization, and dispersibility of agricultural and horticultural insecticides and acaricides. so,
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, and methylnaphthalene. Examples thereof include cyclohexane, animal and vegetable oils, and fatty acids. As the solid carrier, clay, kaolin, talc, diatomaceous earth, silica, calcium carbonate, montmorillonite, bentonite, feldspar, quartz, alumina, sawdust, nitrocellulose, starch, gum arabic and the like can be used. Usable surfactants can be used as emulsifiers and dispersants, for example, anionic surfactants such as higher alcohol sodium sulfate, stearyltrimethylammonium chloride, polyoxyethylene alkylphenyl ether, lauryl betaine, and cations. A nonionic surfactant, a nonionic surfactant, an amphoteric surfactant, and the like can be used. Also,
Spreading agents such as polyoxyethylene nonyl phenyl ether and polyoxyethylene lauryl phenyl ether; Wetting agents such as dialkyl sulfosuccinate; Fixing agents such as carboxymethyl cellulose and polyvinyl alcohol; Disintegration of sodium lignin sulfonate and sodium lauryl sulfate Agents can be used.

The content of the active ingredient in the insecticide for agricultural and horticultural use and the acaricide of the present invention is selected from the range of 0.1 to 99.5%, and may be appropriately determined according to various conditions such as the form of the preparation and the method of application. For example, about 0.5 to 20% by weight, preferably 1 to 10% by weight for powder and about 1 to 10% for wettable powder.
About 90% by weight, preferably about 10 to 80% by weight, and about 1 to 90% by weight, preferably 10 to 40% by weight in emulsion.
It is preferable to manufacture the composition so as to contain the active ingredient described above. For example, in the case of an emulsion, the active ingredient represented by the general formula (I)
An emulsion of a stock solution can be prepared by mixing a solvent, a surfactant and the like with the compound (1), and the stock solution can be further diluted to a predetermined concentration with water before use.
In the case of wettable powders, the active ingredient can be prepared by mixing the above-mentioned compound of the active ingredient, a solid carrier, a surfactant and the like, and then diluting the active ingredient with water to a predetermined concentration before use. . In the case of a 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 a granule, the compound of the active ingredient, the solid carrier and a surfactant can be mixed and used. It can be manufactured by granulation 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 agricultural and horticultural insecticides and acaricides of the present invention include:
In addition to the compound of the present invention, which is an active ingredient, other active ingredients such as other fungicides, insecticides, acaricides, herbicides, insect growth regulators, fertilizers, and soil conditioners may be blended. The method for applying the agricultural and horticultural insecticide and / or 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, and seed treatment. For example, in the case of foliage application, 5 to 1000 pp
m, preferably a solution in a concentration range of 10 to 500 ppm, can be used at an application rate of about 100 to 200 liters 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 to 1000 for soil treatment
Solutions in the ppm concentration range can be used at application rates of the order of 1 to 10 liters 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 kg of seed weight can be applied.

[0019]

The present invention will be described in more detail with reference to the following Examples, Preparation Examples and Test Examples, but the present invention is not limited to these Examples unless it exceeds the gist thereof. Example 1 <N-acetyl-N- [4- (4-trifluoromethylphenoxy) benzyl] -3-ethyl-1-methylpyrazole-5
-N- [4- (4-trifluoromethylphenoxy) benzyl] -3-
Ethyl-1-methylpyrazole-5-carboxylic acid amide 1.0
g of N-methylpyrrolidone (5 ml), 60% sodium hydride (0.2 g) was added, and the mixture was stirred at room temperature for 30 minutes. Then, acetyl chloride (0.6 ml) was added, and the mixture was stirred at room temperature for 30 minutes. The mixture was poured into a saturated aqueous solution of ammonium chloride under ice cooling, and extracted with ethyl acetate. The organic layer was washed with water and saturated saline, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography to obtain 0.51 g of the compound (No. 22) shown in Table 1. n _D ²⁴ 1.5448.

Example 2 <N-methoxymethyl-N- [4- (4-
Synthesis of cyanophenoxy) benzyl] -3-ethyl-1-methylpyrazole-5-carboxylic acid amide> N- [4- (4-cyanophenoxy) benzyl] -3-ethyl-1-methylpyrazole-5-carboxylic acid To a solution of 0.5 g of the amide in 5 ml of N-methylpyrrolidone was added 0.1 g of 60% sodium hydride, and the mixture was stirred at room temperature for 30 minutes. Then, 0.18 g of chloromethyl methyl ether was added, and the mixture was stirred at room temperature for 30 minutes. The mixture was poured into a 1N aqueous sodium hydroxide solution under ice-cooling, and extracted with ethyl acetate. The organic layer was washed with water and saturated saline, and dried over anhydrous sodium sulfate.
The solvent was distilled off, and the residue was purified by silica gel column chromatography to obtain 0.42 g of the compound (No. 67) shown in Table 1. n _D ²⁵ 1.5795.

Example 3 The compounds shown in Table 1 were synthesized according to the method described in Example 1 or 2.

[0022]

[Table 1]

[0023]

[Table 2]

[0024]

[Table 3]

[0025]

[Table 4] *) ¹ H NMR (CDCl ₃ ): d 1.12 (3H, s), 1.16-1.27 (9H,
m), 1.39 (3H, s), 2.62 (2H, q), 2.69 (1H, sept), 3.
98 (3H, s), 4.52 (1H, d), 4.82 (1H, d), 6.37 (1H,
s), 6.95 (2H, d), 6.96 (2H, d), 7.17 (2H, d), 7.49
(2H, d)

Hereinafter, examples of preparations of insecticides and acaricides for agricultural and horticultural use containing the compound of the present invention as an active ingredient are shown, but the use form 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 & Co., Ltd., trade name), ST kaolin clay (kaolinite, Tsuchiya Kaolin Co., trade name) 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., trade name) And a wettable powder of 20% by weight of the active ingredient was obtained.

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 is dissolved in a mixed solvent consisting of 35 parts by weight of xylene and 30 parts by weight of dimethylformamide, and the mixture is mixed with Solpol 3005X (a mixture of a nonionic surfactant and an anionic surfactant). , 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 and 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 this slurry-like mixture, mixed well and pulverized to obtain an active ingredient 20.
By weight, a flowable agent was obtained.

Hereinafter, test examples of agricultural and horticultural insecticides and acaricides containing the compound of the present invention as an active ingredient will be shown, but the use form of the present invention is not limited to the following. Compound A described in JP-A-3-68560 and Compound B described in JP-A-7-112972 were subjected to the same test as control compounds.

[0030]

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Test Example 1: Insecticidal effect on larvae of Spodoptera litura Cut cabbage leaves (diameter 6 cm) were immersed for 1 minute in a water dilution of the insecticide of the present invention produced according to the formulation of Preparation Example 1. Air-dried plastic cup after immersion (7cm inside diameter)
, And in this cup, five third instar insects of Spodoptera litura were released (one concentration, two repetitions). The larvae were kept in a constant temperature room at 25 ° C., and after 5 days from the release, the larvae were examined for life and death and writhing, and the insecticidal activity (%) was determined assuming that the writhing larva was 死 dead. The results are shown in Table 2 (in the following table, compound No. corresponds to Table 1).

[0032]

[Table 5]

Test Example 2: Acaricidal effect on adults of Dermatophagoid spider mite Adults of the adult spider mite per leaf were inserted into a test tube (volume: 50 ml) filled with water and the stem portion of a kidney seedling having one primary leaf left was inserted. Fifteen animals were inoculated. One day after the inoculation, the leaves on which the spider mites were parasitized were immersed (about 5 seconds) in a water dilution of the acaricide of the present invention manufactured according to the formulation of Preparation Example 3 (one concentration, two repetitions). After being kept in a constant temperature room at 25 ° C., on the 5th day after the chemical treatment, the number of adult spider mites on the green leaves was examined, and the adulticidal rate (%) was determined based on the results. The results are shown in Table-3.

[0034]

[Table 6]

[0035]

[Table 7]

[0036]

[Table 8]

[0037]

[Table 9]

[0038]

The pyrazolecarboxylic acid amides of the present invention have an excellent control effect against harmful insects and mites.

 ──────────────────────────────────────────────────続 き Continued on the front page (72) Inventor Yasushi Shiga 1000 Kamoshita-cho, Aoba-ku, Yokohama-shi, Kanagawa Prefecture Inside Mitsubishi Research Institute of Yokohama, Ltd. Chemical Research Co., Ltd. Yokohama Research Laboratory F-term (reference) 4H011 AC01 AC04 BA01 BA05 BB09 BC01 BC06 BC18 BC20 DA02 DA15 DA16

Claims (5)

[Claims] 1. A compound represented by the following general formula (I)(Where R¹Is C₁-C_Three Acyclic or cyclic alkyl of
Group, C₁-C_FourAn alkoxy group or trifluoromethyl
Represents a group. R^TwoIs C_Two-C_Five An acyl group of C_Two-C_TenOki
Soacyl group, C_Two-C_Ten An alkoxycarbonyl group,
A phenoxycarbonyl group which may have a substituent,
A benzoyl group which may be present, C_Two-C_Five The alkoxymethy
Group, a pyridylmethyl group which may have a substituent, C_Three-C
₆An alkoxycarbonylmethyl group, ethyloxalyl
Group or a cyanomethyl group. R ^Three Is a hydrogen atom, shear
No group, C₁-C_Four An alkylthio group of C₁-C_FourThe alkyl of
Sulfinyl group, C₁-C_Four Alkylsulfonyl group of C
₁-C_Four Haloalkyl group, nitro group, halogen atom, C
₁-C_FourAn alkyl group of C₁-C_FourAn alkoxy group of C₁-C
_FourHaloalkoxy group or C₁-C_FiveAcylamino group of
Is shown. R^FourIs a hydrogen atom or C₁-C_FourThe alkyl group of
Pyrazolecarboxylic acid amides represented by: 2. The pyrazolecarboxylic acid amide according to claim 1, wherein in the general formula (I), R ¹ is a methyl group, an ethyl group or a methoxy group. 3. The compound according to claim 1, wherein R ² is a C ₂ -C ₅ acyl group, a C ₂ -C ₁₀ oxoacyl group or a C ₂ -C ₅ alkoxymethyl group. 1
Or the pyrazolecarboxylic acid amides according to 2. 4. The pyrazole carboxylic acid amide according to claim 1, wherein R ⁴ in the general formula (I) is a hydrogen atom. 5. An insecticide and acaricide comprising the pyrazolecarboxylic acid amide according to claim 1 as an active ingredient.