JP2001199984A - Pyrazole-5-carboxylic acid amide, and insecticide and acaricide containing the same as active ingredient - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a compound exhibiting high controlling effect even against various noxious insects having resistance against a conventional insecticide or acaricide, and reduced in the problems such as residual toxicity and environmental pollution. SOLUTION: A pyrazole-5-carboxylic acid amide of the general formula (1) (wherein, R1 is an alkyl; R2 is hydrogen or an alykyl; R3 and R4 are each independently hydrogen, cyano, an alkylthio, an alkylsulfinyl, an alkylsulfonyl, a haloalkyl, nitro, a halogen, an alkyl, an alkoxy, a haloalkoxy or phenylethynyl).

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to novel pyrazole-5-carboxylic acid amides and an insecticide and acaricide containing the pyrazole-5-carboxylic acid amides as an active ingredient.

[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.

[0003] Also, the appearance of pests that have acquired resistance to conventional agricultural chemicals has become a problem. For example, vegetables,
In cultivation of fruit trees, flowers, tea, wheat and rice,
Various types of pesticides, for example, carbamates, pyrethroids, benzoylureas, organochlorines, organophosphorus pesticides, and other various pests that have acquired resistance have appeared in various places and are caused by these pests The control of various pests is becoming more difficult year by year. Therefore, it is desired to develop a novel insecticide that shows sufficient control effect at a low dose even for various pests that have acquired resistance to general-purpose agricultural and horticultural insecticides and that has little adverse effect on the environment. ing. As for the acaricide, the development of a highly safe acaricide that exhibits an excellent control effect on mites that have resistance to conventional acaricides has been expected.

Various studies have been made on pyrazole-5-carboxylic acid amides similar to those of the present invention. 1) JP-A-2-62876, 2) JP-A-7-
JP-A-173139, 3) JP-A-8-277287, 4) JP-A-9-278775, 5) JP-A-1
Japanese Patent Application No. 0-053583 describes that N- (pyridylmethyl) pyrazole-5-carboxylic acid amides similar to the present invention are useful as insecticides, miticides, and fungicides. However, the compounds described in these publications include: a) a nitrogen atom on the amide is not acylated, or b) a combination of an alkyl group at the 3-position of the pyrazole ring and a hydrogen atom at the 4-position. Only.

[0005] Japanese Patent Application Laid-Open Nos. 3-68560 and 10-53582 also describe compounds similar to the present invention. However, 6- (substituted phenoxy) pyridine-3-type compounds as in the present invention are disclosed. There is no description about compounds having an ylmethyl structure. Examples of the compound in which the 3-position of the pyrazole ring is an alkyl group and the 4-position is a hydrogen atom are limited to the following three compounds.

[0006]

Embedded image

The compounds described in the above-mentioned prior arts have problems such as insufficient insecticidal and acaricidal activity, narrow spectrum and high toxicity to mammals.

[0008]

An object of the present invention is to exhibit a high control effect against various insect pests which are resistant to conventional insecticides and acaricides, and useful as an active ingredient of insecticides and acaricides. To provide chemicals. Another object of the present invention is to provide a highly safe insecticide and acaricide having the above-mentioned features and having reduced problems such as residual toxicity and environmental pollution.

[0009]

The present inventors have conducted intensive studies to solve the above-mentioned problems. As a result, the 3-position of the pyrazole ring is an alkyl group, the 4-position is a hydrogen atom, and the 6- (substituted) The present inventors have found that specific novel pyrazole-5-carboxylic acid amides having a phenoxy) pyridin-3-ylmethyl structure are compounds that solve the above-mentioned problems, and have completed the present invention. That is, the gist of the present invention is represented by the following general formula (I)

[0010]

Embedded image

(In the formula, R ¹ represents an alkyl group, R ² represents a hydrogen atom or an alkyl group. R ³ and R ⁴ each independently represent a hydrogen atom, a cyano group, an alkylthio group, an alkylsulfinyl group, an alkylsulfonyl. Group, a haloalkyl group, a nitro group, a halogen atom, an alkyl group, an alkoxy group, a haloalkoxy group or a phenylethynyl group.) And a pyrazole-5-carboxylic amide. Insects and miticides contained as active ingredients.

[0012]

BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in detail.
The substituent R ¹ of the compound of the present invention represented by the general formula (I) is
Methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-
It represents an alkyl group such as a butyl group, of which a C ₁ -C ₄ alkyl group is preferred. R ² represents a hydrogen atom; an alkyl group such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group and a tert-butyl group. Among them, as the alkyl group, C ₁
Ones -C ₄ are preferred. R ³ and R ⁴ are each independently
Hydrogen atom; cyano group; alkylthio group such as methylthio group, ethylthio group, propylthio group, isopropylthio group, butylthio group, isobutylthio group, sec-butylthio group, tert-butylthio group; methylsulfinyl group, ethylsulfinyl group, propylsulfinyl Group,
Isopropylsulfinyl group, butylsulfinyl group,
Alkylsulfinyl groups such as isobutylsulfinyl group, sec-butylsulfinyl group and tert-butylsulfinyl group; methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group, isopropylsulfonyl group, butylsulfonyl group, isobutylsulfonyl group, s
alkylsulfonyl groups such as ec-butylsulfonyl group and tert-butylsulfonyl group; haloalkyl groups such as trifluoromethyl group, difluoromethyl group, trichloromethyl group and pentafluoroethyl group; nitro group; fluorine atom, chlorine atom and bromine atom And halogen atoms such as iodine atom; methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, te
alkyl group such as rt-butyl group; methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, alkoxy group such as isobutoxy group, sec-butoxy group, tert-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, 2,2,3,3-tetra A haloalkoxy group such as a fluoropropoxy group, 2,2,3,3,4,4,4-heptafluorobutoxy group; and a phenylethynyl group. Among them, alkylthio group, alkylsulfinyl group, alkylsulfonyl group, haloalkyl group,
The carbon number of the alkyl group, alkoxy group and haloalkoxy group is preferably C ₁ -C ₄ . Among them, R ³ is preferably a cyano group, a methylthio group or a trifluoromethyl group. R ⁴ is preferably a hydrogen atom.

Further, as a combination of the above substituents, a compound in which R ³ is a cyano group, a methylthio group or a trifluoromethyl group and R ⁴ is a hydrogen atom is particularly preferable. The compound of the present invention can be obtained, for example, by producing a compound represented by the following general formula (II) by a known method (for example, a method described in JP-A-2-62876), and then acylating the compound. Can be done. Examples of the acylation method include the following methods.

[0014]

Embedded image

(Wherein R ¹ , R ² , R ³ and R ⁴ are as defined in the above formula (I), and Y represents a chlorine atom or a bromine atom). Is reacted with an acyl halide represented by the general formula (III) in the presence or absence of a base, preferably using a solvent, at -10 to 150 ° C. 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; halogens such as chloroform and dichloromethane. Water; esters such as ethyl acetate and methyl acetate; or tetrahydrofuran;
Examples thereof include polar solvents such as 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; Examples include amines.

[0016]

Embedded image

(In the above formula, R ¹ , R ² , R ³ and R ⁴ are as defined in the general formula (I).) That is, the pyrazole-5-carboxylic acid represented by the general formula (II) The amide is reacted with the acid anhydride represented by the general formula (IV) 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, for example, benzenesulfonic acid,
Sulfonic acids such as p-toluenesulfonic acid, methanesulfonic acid, ethanesulfonic acid, and trifluoromethanesulfonic acid; and inorganic acids such as sulfuric acid, hydrochloric acid, and phosphoric acid.

After the reaction described in the above-mentioned production method 1 or 2, in order to isolate the target compound represented by the general formula (I), a solvent soluble in water is used. Is distilled off, water is added, and then water-insoluble benzene, toluene,
Aromatic hydrocarbons such as xylene; halogenated hydrocarbons such as chloroform and dichloromethane; extracted with esters such as ethyl acetate, washed with saturated saline, and dried with a drying agent such as anhydrous sodium sulfate and anhydrous magnesium sulfate; 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 a general purification method such as recrystallization, suspension washing, column chromatography, etc. to obtain the desired compound represented by the general formula (I). Can be obtained. The compound 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, Anemone brassicae, Lepidoptera, Scarabaeidae; planthoppers such as brown planthoppers and scabies; leafhoppers such as leafhoppers and leafhoppers; Hemiptera, such as aphids, whiteflies such as whiteflies, and white bugs such as whiteflies; stink bugs such as leaf stink bugs; Coleoptera such as flea beetles, turtle beetles, and azuki beetles; Insect larvae and adults, as well as spider mites, citrus red mite, citrus red mite, Dermatophagoides mite, etc., and has a high control effect on pests of agricultural and horticultural crops such as larvae and adults. Insecticides and acaricides It is useful as an active ingredient. 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 general formula (I) is used as an insecticide or acaricide for agricultural and horticultural use, it may be used alone, but preferably is an agricultural chemical adjuvant commonly used in the art. It is used in the form of a composition produced using Agricultural and horticultural insecticides, forms of miticides are not particularly limited,
For example, they are preferably in the form of emulsions, wettable powders, aqueous solvents, powders, flowables, fine granules, granules, tablets, oils, sprays, aerosols and the like. One or more of the above compounds can be blended as an active ingredient. Agricultural and horticultural insecticides, pesticide adjuvants used to produce acaricides, agricultural and horticultural insecticides, improve the effect of acaricides, stabilization, for the purpose of improving dispersibility, for example, , A carrier (diluent), a spreading agent, an emulsifier, a wetting agent, a dispersant, a disintegrant, and the like.

Liquid carriers 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 dimethylsulfoxide, and the like. Examples thereof include methylnaphthalene, cyclohexane, animal and vegetable oils, and fatty acids. Also,
Clay, kaolin, talc, diatomaceous earth,
Silica, calcium carbonate, montmorillonite, bentonite, feldspar, quartz, alumina, sawdust, nitrocellulose, starch, gum arabic and the like can be used.

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. And cationic surfactants, nonionic surfactants, amphoteric surfactants, and the like. A spreading agent such as polyoxyethylene nonyl phenyl ether and polyoxyethylene lauryl phenyl ether; a wetting agent such as dialkyl sulfosuccinate; carboxymethyl cellulose;
Fixing agents such as polyvinyl alcohol; disintegrating agents such as sodium ligninsulfonate and sodium lauryl sulfate 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% by weight, and is appropriately determined according to various conditions such as the form of the preparation and the method of application. However, for example, about 0.5-20
% By weight, preferably 1 to 10% by weight, about 1 to 90% by weight, preferably 10 to 80% by weight for wettable powders, and about 1 to 90% by weight, preferably 10 to 40% by weight for emulsions. It is preferable to manufacture the composition so as to contain the active ingredient.

For example, in the case of an emulsion, a solvent and a surfactant can be mixed with the compound of the general formula (I) as an active ingredient to produce an emulsion of a stock solution. It can be diluted with water and applied. 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.

[0026]

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 3-tert-butyl-N-isobutyryl-1-methyl-N- [6- (4-methylthiophenoxy) pyridine-
Synthesis of 3-ylmethyl] pyrazole-5-carboxylic acid amide 3-tert-butyl-1-methyl-N- [6- (4-
Methylthiophenoxy) pyridin-3-ylmethyl] pyrazole-5-carboxamide (0.63 g) N-
To a solution of methylpyrrolidone (5 ml) was added 60% sodium hydride (0.1 g), and the mixture was stirred at room temperature for 30 minutes. Then, isobutyryl chloride (0.4 ml) was added under ice-cooling.
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.
1 g was obtained. The compounds shown in Table 1 were synthesized according to the method described in Example 1.

[0027]

[Table 1]

Of the compounds shown in Table 1, those of viscous compounds are described below in terms of ¹ H NMR data. Compound 1: ¹ H NMR (CDCl ₃ ): 1.28 (9H, s), 2.18 (3H,
s), 3.95 (3H, s), 4.97 (2H, s), 6.29 (1H, s), 6.93
(1H, d, J = 8.4 Hz), 7.21 (2H, d, J = 8.4 Hz), 7.6
4 (2H, d, J = 8.4 Hz), 7.70 (1H, d, J = 8.4 Hz),
8.05 (1H, s) Compound 9: ¹ H NMR (CDCl ₃ ): 0.99 (6H, d, J = 6.6 Hz),
1.27 (9H, s), 2.56 (1H, sept, J = 6.6 Hz), 4.00
(3H, s), 4.90 (2H, s), 6.21 (1H, s), 6.88 (1H, d,
J = 8.4 Hz), 7.05 (2H, d, J = 8.7 Hz), 7.34 (2H,
d, J = 8.7 Hz), 7.75 (1H, dd, J = 2.4, 8.4 Hz), 8.
13 (1H, d, J = 2.4 Hz) Compound 10: ¹ H NMR (CDCl ₃ ): 0.99 (6H, d, J = 6.6 H)
z), 1.27 (9H, s), 2.49 (3H, s), 2.57 (1H, sept, J =
6.6 Hz), 4.00 (3H, s), 4.90 (2H, s), 6.21 (1H,
s), 6.83 (1H, d, J = 6.3 Hz), 7.05 (2H, d, J = 8.7
Hz), 7.29 (2H, d, J = 8.7 Hz), 7.73 (1H, dd, J =
2.1, 6.3 Hz), 8.14 ( 1H, d, J = 2.1 Hz) Compound _{^{11: 1 H NMR (CDCl 3}} ): 0.99 (6H, d, J = 6.6 H
z), 1.27 (9H, s), 2.56 (1H, sept, J = 6.6 Hz), 4.01
(3H, s), 4.92 (2H, s), 6.22 (1H, s), 6.94 (1H, d,
J = 8.4 Hz), 7.21 (2H, d, J = 8.3 Hz), 7.64 (2H,
d, J = 8.4 Hz), 7.80 (1H, dd, J = 2.4, 8.7 Hz), 8.1
6 (1H, d, J = 2.4 Hz) Compound 12: ¹ H NMR (CDCl ₃ ): d 0.99 (6H, d, J = 6.6)
Hz), 1.27 (9H, s), 2.56 (1H, sept, J = 6.6 Hz),
4.00 (3H, s), 4.90 (2H, s), 6.21 (1H, s), 6.86 (1
H, d, J = 8.7 Hz), 7.1 (4H, m), 7.74 (1H, dd, J =
2.4, 8.7 Hz), 8.13 (1H, d, J = 2.4 Hz)

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 form of use 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 are shown, but the form of use of the present invention is not limited to the following. Test Example 1: Insecticidal effect on Japanese larvae of Japanese moth Cabbage leaves (6 cm in diameter) were immersed in a water dilution of the insecticide of the present invention produced according to the formulation of Preparation Example 3 for 1 minute. Air-dried plastic cup after immersion (7cm inside diameter)
, And 5 of the 3rd instar moths were released into this cup (1 concentration, 2 repetitions). The larvae were kept in a constant temperature room at 25 ° C., and after 4 days from the release, the larvae were examined for viability and agony.
The insecticidal activity (%) was determined as the death of two animals. The results are shown in Table 2 (in the table below, the compound numbers correspond to Table 1).

[0033]

[Table 2]

Test Example 2: Acaricidal effect on adults of Dermatophagoides pteronyssima Into a test tube (capacity: 50 ml) filled with water, the stem portion of a bean seedling, leaving one primary leaf, 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 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 Tables 3 and 4. Compound A described in JP-A-3-68560 was subjected to the same test as a control compound.

[0035]

Embedded image

[0036]

[Table 3] Compound No. Concentration (ppm) Acaricidal rate (%) ──────────────────────── 1500 100 2 500 100 3 500 100 4 500 100 5 500 100 8 500 100 9 500 100 10 500 100 11 11 500 100 12 12 500 100 13 500 100 14 14 500 100 15 500 100 16 500 100 17 17 500 100 ───

[0037]

[Table 4] Compound No. Concentration (ppm) Acaricidal rate (%) ──────────────────────── 150 100 1 12.5 100 A 50 100 A 12.50 ────────────────────────

[0038]

Industrial Applicability The pyrazole-5-carboxylic acid amides of the present invention have an excellent control effect on harmful insects and mites.

 ──────────────────────────────────────────────────続 き Continuing on the front page (72) Inventor Yasushi Shiga 1000 Kamoshita-cho, Aoba-ku, Yokohama-shi, Kanagawa Prefecture Inside Mitsubishi Chemical Research Institute (72) Inventor Toshiki Fukuchi 1000 Kamoshita-cho, Aoba-ku, Yokohama-shi, Kanagawa Mitsubishi F-term in Yokohama Research Laboratory (reference) 4C063 BB09 CC22 DD12 EE03 4H011 AC02 AC04 BA05 BB09 BC03 BC04 BC07 BC20 DA02 DA15 DC05 DD03 DE14 DF04

Claims (5)

[Claims] 1. A compound represented by the following general formula (I) (Wherein, R ¹ represents an alkyl group, R ² represents a hydrogen atom or an alkyl group. R ³ and R ⁴ each independently represent a hydrogen atom, a cyano group, an alkylthio group, an alkylsulfinyl group, an alkylsulfonyl group, a haloalkyl Pyrazole-5-carboxylic acid amides represented by a nitro group, a nitro group, a halogen atom, an alkyl group, an alkoxy group, a haloalkoxy group or a phenylethynyl group. 2. R¹Is C₁-C_FourIs an alkyl group of^Two
Is a hydrogen atom or C ₁-C_FourRepresents an alkyl group represented by^Three,
R^FourIs independently a hydrogen atom, a cyano group, C ₁-C_Fourof
Alkylthio group, C₁-C_FourAn alkylsulfinyl group of
C₁-C _Four Alkylsulfonyl group of C₁-C_FourNo haloal
Kill group, nitro group, halogen atom, C₁-C_FourThe alkyl of
Group, C₁-C_FourAn alkoxy group of C₁-C_FourThe haloalkiko
Characterized by being a xy group or a phenylethynyl group
Pyrazole-5-carboxylic acid amides. 3. The pyrazole-5-carboxylic acid amide according to claim 1, wherein R ³ is a cyano group, a methylthio group or a trifluoromethyl group. ^4. The pyrazole-5-carboxylic acid amide according to claim 1, wherein R ⁴ is a hydrogen atom. 5. The pyrazole-5 according to claim 1, wherein
Insecticides and miticides containing carboxylic amides as active ingredients.