JP2002284781A - Pyrazole derivative and pest controlling agent using the same as active ingredient - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a pest controlling agent having a high penetration transfer activity and reduced toxicity against surroundings of application. SOLUTION: This compound is a derivative of 1-aryl-3-cyano-5- heteroarylalkylaminopyrazole expressed by formula (1). (X is N or a C-halogen group; R<1> is a haloalkyl or a halogen atom; R<2> is H or an alkyl or an acyl; R<3> is H or an alkyl, A is group of formula A-1 to A-4; R<4> is H, an alkyl or a halogen atom; and m and n are each 0 or 1).

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a novel 1-aryl-3-cyano-5-heteroarylalkylaminopyrazole derivative and a pesticidal composition containing the same as an active ingredient.

[0002]

2. Description of the Related Art Conventionally, in the field of agriculture and horticulture, various pesticides such as insecticides for controlling various pests have been developed and put to practical use. For example, pyrazole compounds having insecticidal activity include those described in JP-A-62-228065, JP-A-63-316771, and JP-A-3-3127.
JP-A-118369 discloses a 3-cyano-1-phenylpyrazole derivative having an amino group which may be substituted at the 5-position, and JP-A-5-148240 discloses a substituted 1-aryl-3. -Cyano-5- (het) arylmethylideneiminopyrazole derivatives are disclosed. Further, Japanese Patent Application Laid-Open No. Sho 47-47768 discloses substituted 1-aryl-5- (het) arylmethylaminopyrazole derivatives. It has been disclosed.

[0003] However, the compounds described in the above-mentioned documents do not satisfy all of the insecticidal effect, insecticidal spectrum, safety and the like, and there has been a demand for the emergence of a novel compound which has overcome these problems. The present inventors have previously developed a novel 1-aryl-3-cyano-5-
WO9845274 and WO200100 as heteroarylalkylaminopyrazole derivatives
No. 614 was found.

However, there is no description in this application of a compound in which the substituent at the 4-position of the pyrazole ring is a haloalkyl group or a halogen atom.

[0005]

[Problems to be solved by the invention]

[0006]

The gist of the present invention is as follows.

[0007]

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1-aryl-3-cyano-5 represented by the formula
A heteroarylalkylaminopyrazole derivative and a pesticidal composition containing the same as an active ingredient. Hereinafter, the present invention will be described in detail.

[0009]

DETAILED DESCRIPTION OF THE INVENTION In the present invention [the compound of the present invention, the substituents R ¹ is fluoromethyl group in the compound represented by the above general formula (1), a difluoromethyl group, a 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-tetrofluoropropyl group,
2,2,3,3,3-pentafluoropropyl group, 2,
2-dichloro-3,3,3-trifluoropropyl 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-trifluorobutyl group, 3,3,4,
Represents a straight-chain or branched-chain haloalkyl group such as a 4,4-pentafluorobutyl group or a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, and R ¹ is particularly preferably C ₁ to C ₂ It is a haloalkyl group. R
² is a hydrogen atom; methyl, ethyl, n-propyl,
Isopropyl group, n-butyl group, isobutyl group, sec
Straight-chain or branched-chain alkyl groups such as -butyl group, t-butyl group and the like; or methylcarbonyl group, ethylcarbonyl group, n-propylcarbonyl group, isopropylcarbonyl group, n-butylcarbonyl group, isobutylcarbonyl group, sec-butyl It represents a straight-chain or branched-chain acyl group such as a carbonyl group and a t-butylcarbonyl group, and the alkyl group or the acyl group is preferably a C ₁ -C ₄ group. R ² is particularly preferably a hydrogen atom.

R ³ is a hydrogen atom; or a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group,
It represents a linear or branched alkyl group such as an isobutyl group, a sec-butyl group and a t-butyl group, and the alkyl group is preferably a C ₁ -C ₄ group. R ³ is particularly preferably a hydrogen atom. A is any group represented by A-1 to A-4, and among them, A-1 is preferable.
R ⁴ is a hydrogen atom; methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s
a straight-chain or branched-chain alkyl group such as an ec-butyl group or a t-butyl group; or a halogen atom such as a chlorine atom, a fluorine atom or a bromine atom, of which an alkyl group is preferably a C ₁ -C ₄ group. . R ⁴ is particularly preferably a hydrogen atom.

X is an N or C-halogen atom, preferably a C-halogen atom, particularly preferably a C-chlorine atom. m or n is either 0 or 1. As the compound of the above general formula (1), a compound obtained by combining preferred substituents in the description of the above substituents is a more preferable compound.

Among these, preferred compounds as a combination of substituents are haloalkyl groups R ² and R _{1 wherein} R ¹ is C ₁ to C _2.
³ and R ⁴ are hydrogen atoms, X is a C-Cl group, and A is A-
1 is the compound. [Method for Producing Compound of the Present Invention] As a method for producing the compound of the present invention represented by the general formula (1), usually, after forming a substituted pyrazole ring, a substituent is added or changed as necessary. Manufactured.

A known method is disclosed in JP-A-63-3167.
No. 71, WO9828278, WO2001
Methods described in JP-A No. 00614 and the like are exemplified, and as a production method using these methods, the methods of the following reaction formulas 1 to 4 are exemplified.

[0014]

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In the above formula, R ¹ , R ² , R ³ , A and X have the same meanings as in the general formula (1), and X ¹ is a halogen atom, a hydroxyl group,
It represents a leaving group such as an alkoxy group, and X ² represents a halogen atom. As shown in the reaction formula 1 or 2, the compound represented by the general formula (1) is obtained by coupling the amino group-containing compound with a halide using the compounds represented by the general formulas (2) and (3) as raw materials. Pyrazole derivatives can be produced.

As shown in Reaction Scheme 3, a compound of the general formula (2) is used as a raw material to first obtain AC (ＡO) —X ²
And an amide compound (4), which is reduced. Another example is a method in which the amide compound (4) is converted into a haloimidate compound (5), and this is reduced to obtain a pyrazole derivative. Further, as shown in Reaction Scheme 4, first, A-
A method of reacting with C (＝ O) —R ³ to obtain an imine compound and reducing the imine compound is exemplified.

Solvents used in the amidation reaction include acetonitrile, DMF, DMSO, HMPA, NMP, DM
Illustrative are non-polar protic solvents such as I and aromatic solvents such as benzene, toluene and xylene, and toluene is preferred. The amount of the solvent used is 1- to 100-fold, preferably 1- to 10-fold, relative to the substrate.

The reaction is carried out at a temperature ranging from -20 ° C to 120 ° C, preferably from 0 ° C to room temperature. The reaction time is from 1 hour to 24 hours, preferably from 1 to 4 hours. This reaction is preferably performed in the presence of a base. As bases, sodium methylate, sodium ethylate, te
Examples thereof include alcoholates such as rt-butoxy potassium and alkali metals such as sodium metal and potassium metal. The amount of the catalyst is exemplified by a 2-fold molar amount to the catalytic amount of the heterocyclic carboxylic acid, but is preferably 0.5 to 1.5-fold. As the alcoholate, a powder or an alcohol solution is used.

The reducing agent used in the reduction reaction includes borane THF complex, sodium borohydride, sodium cyanoborohydride, lithium borohydride or lithium aluminum hydride. Solvents used in this reaction include ethers such as diethyl ether, dioxane or tetrahydrofuran; or methanol,
Examples include polar solvents such as alcohols such as ethanol and propanol. The reaction is carried out at a temperature in the range of -20 ° C to 120 ° C, preferably 0 ° C to room temperature, and is carried out for 1 hour to 24 hours, preferably for 1 to 4 hours.

Examples of the chlorinating agent used for haloimidate formation include phosphorus pentachloride, phosphorus oxychloride, thionyl chloride and the like. Examples of the solvent used in this reaction include aromatic solvents such as benzene, toluene and xylene; halogen solvents such as carbon tetrachloride, chloroform and dichloromethane; and ether solvents such as dimethoxyethane and tetrahydrofuran.

The reaction is carried out at 0 ° C. to 200 ° C., preferably at room temperature to
It is carried out in the range of 150 ° C. and is carried out for 1 to 24 hours, preferably for 1 to 4 hours. Examples of the solvent used in the imination reaction include polar solvents such as alcohols such as methanol, ethanol and propanol, and hydrocarbon solvents such as benzene, toluene and hexane.

The compounds described in the general formula (1) can be produced by combining the methods described above. [Uses of the compound of the present invention] The pesticidal composition containing the compound of the present invention as an active ingredient has an effect of controlling pests, mites and other pests. For example, agriculture, forestry, animal husbandry, fisheries, and products of these industries It is effective in repelling pests, controlling and controlling pests in a wide range of situations such as preservation and public health. In particular, the compound of the present invention is used in agriculture, forestry, and the like, specifically, when cultivating crops, and when repelling, controlling, and controlling pests that damage the crops, trees, ornamental plants, and the like, and in public health situations. As insecticides and miticides used for
Demonstrates excellent effects.

[0023] The specific use scene, target pest,
The method of use and the like will be described, but the present invention is not limited to the following description. The pests specifically exemplified are not limited to target pests, and the exemplified pests also include adults, larvae, eggs, and the like. (A) Agriculture, forestry, etc .; Pest control agents containing the compound of the present invention as an active ingredient include agricultural crops such as food crops (rice, barley, corn, potato, sweet potato, beans, etc.), vegetables (brassaceae crops, Spinach, eggplant, tomato, leek, etc.), fruit trees (citrus, apple, grape, thigh, etc.), special crops (tobacco, tea, sugar beet, sugar cane, cotton, olives, etc.), pasture and feed crops (sorghum) , Grasses, legumes, etc.)
And repelling and controlling pests such as arthropods, molluscs, nematodes, and various fungi that damage them when cultivating plants and ornamental plants (herbs, flowers, garden trees, etc.) It is valid. Further, the compound of the present invention can be used to repel pests when storing harvested products from the above-mentioned crops, such as cereals, fruits, nuts, spices, tobacco, and the like, and products that have been subjected to drying, powdering, and the like. It is also effective for extermination. It is also effective in protecting standing trees, fallen trees, processed wood, stored wood, and the like from damage by pests such as termites and beetles.

Specific pests include, for example, those belonging to the phylum Arthropoda, Mollusca and Nematoda.
The following can be mentioned. Examples of the arthropod phylum Insecta include the following. As Lepidoptera, for example, Noctuidae such as Spodoptera litura, Tobacco armyworm, Armyworm, Tamanagininuwaba;
Anthophoridae, such as Anopheles japonicus and Papilio persica; Aminidae, such as Mina moga; Pterodaceae such as peach sink moth; Singing moth such as peach sink moth; Iragidae such as iraga; Lycaenidae of the family; Paeoniaceae such as Artemisia japonica; Sphingidae such as prawns; It can gel.

As the order Coleoptera, for example, Scarabaeidae, for example, Scutellaria buoyii, Scutellariae japonicus, Mamekogane etc .;
Beetles, such as Citrus beetles; Beetles, such as Marc beetles; Weevil family; honey beetle weevil family such as arid beetle; weevil family such as weevil weevil and rice weevil.

As the Hemiptera, for example, stink bugs such as chafered stink bugs and sting bugs; crested stink bugs such as pear stink bugs; helicopter custody members such as stag beetles; Gastropodidae such as Nashigumbai; Scarabaeidae such as Pseudomonidae; Cicadaidae such as Nichiniizemi; Coleoptera such as Grape Awafuki;
Lepidoptera, such as the leafhopper leafhopper and the leafhopper leafhopper; Lepidoptera, such as the leafhopper leafhopper; Phylloceraceae, such as Krya aphid; Berberidae, such as apple beetle; Aphid, such as cotton aphid, peach aphid, and okabonoa aphid; And other insects;

Examples of the thrips include Thrips (Thysanoptera: Thrips), Thrips palmi (Thrips thrips), Thrips palmi (Thysanoptera) and Thrips (Thysanoptera: Thrips), such as Thrips palmi, Thrips and Thrips. Examples of the Hymenoptera include honeybees, such as wasps, honeybees, etc .; honeybees, such as apple honeybees; honeybees, such as chestnut wasps; and honeybees, such as rosehip bees.

Examples of the diptera include, e.g., soybean flies, e.g., soybean flies; flies, e.g. Department. As the Orthoptera, for example, grasshoppers such as crickets; crickets such as green worms;
And the like; and the like;

As the order of the order Collembola, there may be mentioned, for example, bryozoan family, such as the yellow worm, etc .; Examples of the termites include termites such as Taiwan termites, and examples of the earwigs include earwigs such as earwigs.

Examples of arthropod phylum crustaceans and arachnids include the following. As the isopod of the crustacean, there may be mentioned, for example, the family Acaratidae, such as the cadaver bug. As the spider mite of the order of the spiders, for example, Dermatophagoids such as Dermatophagoids and Cyclamenidae;
Red mite, such as wheat mite; Red mite, such as grape spider mite; Spider mite, such as spider mite, Kanzawa mite, red mite, apple spider mite; it can.

The mollusc phylum Gastropods include, for example, the midgastropods of the gastropods, such as the scallop, and the stalked eyes include, for example, African snails, slugs, skull slugs, chacoura slugs, and Oskawa maime. be able to. The following can be illustrated as examples of the nematode phylum and the tail line. Examples of the genus Genus Nematoda include, for example, Anguinaceae, such as Imogusa nematode; Tilenkorinkusu, such as Namiikusu nematode; Platylenx, such as Kitanegusa nematode, and Minaminekusa nematode; Hoplolymaceae, such as Namila nematode; Heterodela family such as nematodes; meloidoginaceae such as sweet potato nematodes; criconiaceae such as nematodes; nototilencaceae such as strawberry nematodes; and aphelencoides such as strawberry nematodes.

Examples of the order Oxodidae include the Longiduridae family, such as the genus Nematoda, and the Trichodulaceae family, such as the Yumihari nematode. Further, the compound of the present invention is also effective for repelling, controlling, and controlling pests that damage trees or affect tree vigor such as natural forests, artificial forests, and urban green spaces. In such a situation, specific pests include the following. Examples of the arthropod phylum Insecta and Arachnida include the following.

Examples of the Lepidoptera include, for example, Scutellariae such as Sugidokuga and Gypsy moth; Kalehagaceae such as Matsukareha and Tsugakareha; Megumiidae such as Larix sylvestris; Noctuidae such as Kaburayaga; Hirrigidae, such as A. americana; Moglitiviga, such as Shiimoglitiviga;

As the Coleoptera, for example, Scarabaeidae such as Himekogane and Nagachakogane; Tenebrionidae such as Pseudocarabidae; Cerambycidae such as pine beetle; Chrysomelidae such as cedar beetle; Weevil weevil, weevil weevil such as weevil weevil A beetle family, such as a weevil, etc .; a bark beetle family, such as a pine bark beetle and a bark beetle;

The Hemiptera includes, for example, aphid family such as Aphid aphid; mosquito aphid family such as Scotch moss; aphid family such as cedar marcae; and an aphid family such as horn beetle. Examples of the Hymenoptera include honeybees such as larch red wasp; pine wasps such as pine wood wasps; and honeybees such as chestnut wasps.

Examples of the order Diptera include the family Amaryllidaceae such as P. cricket, the genus Asteridae such as L. japonicus, and the flies of the genus Pteridophyta such as L. japonicus and P. aeruginosa. Examples of the spiders of the order Arachnida include spider mite, spider mite and the like.

Examples of the nematodes of the order Nematoda: Parasitaferenidae such as pine wood nematodes. The pesticidal composition containing the compound of the present invention as an active ingredient can be used alone or in addition to other active compounds such as insecticides, pesticides, and the like in the above-mentioned formulation effective in agriculture and forestry, and in any use form prepared by the formulation. It can be used in combination or as a mixture with mites, nematicides, fungicides, synergists, plant regulators, herbicides, poison baits and the like. Specific examples of the above other active compounds include:
The following can be exemplified, but the present invention is not limited to these.

Active compounds such as insecticides and acaricides: Examples of organic phosphorus agents include dichlorvos, fenitrothion, malathion, naled, chlorpyrifos, diazinon, tetrachlorovinphos, fenthion, isoxathion, and the like.
Methidathion, salicion, acephate, dimeton-S
Methyl, disulfotone, monocrotophos, azinephosmesyl, parathion, hosalon, pirimiphosmethyl, prothiophos and the like can be mentioned. Examples of the carbamate include metorcarb, fenobcarb, propoxur, carbaryl, ethiophenecarb, pirimicarb, bendiocarb, carbosulfan, carbofuran, mesomil, thiodicarb and the like.
Examples of the organic chlorine agent include lindane, DDT, endosulfan, aldrin, chlordane and the like. Examples of pyrethroids include permethrin,
Cypermethrin, deltamethrin, cyhalothrin, cyfluthrin, acrinatrine, fenvalerate, etofenprox, silafluofen, fulvalinate,
Flucitrinate, bifenthrin, allethrin, phenothrin, fenpropatrin, cyphenothrin, framethrin, resmethrin, transfluthrin, praletrin, flufenprox, halofanprox, imiprothrin and the like can be mentioned. Neonicotinoid agents include, for example, imidacloprid, nitenpyram, acetamiprid, tefuranitodine, thiamethoxam, thiacloprid and the like.

Examples of insect growth regulators such as phenylbenzoylurea agents include diflubenzuron, chlorofluazuron, triflumuron, flufenoxuron, hexaflumuron, lufenuron, teflubenzuron, buprofezin, tebufenozide, chromafenozide, methoxyfenozide, cyromazine and the like. be able to.

Examples of the juvenile hormone agent include pyriproxyfen, phenoxycarb, mesoprene, hydroprene and the like. Examples of insecticidal substances produced by microorganisms include abamectin, milbemectin, nikkomycin, emamectin benzoate,
Ivermectin, spinosadado and the like can be mentioned.

Examples of other insecticides include cartap, bensultap, chlorfenapyr, diafenthiuron, nicotine sulfate, methaldehyde, fipronil, pymetrozine, indoxacarb, tolfenpyrad and the like. As active compounds for acaricides, for example, dicophor, phenisobromolate, benzomate, tetradiphone, polynactin complex, amitraz, propargyl, fenbutatin oxide, tricyclohexyltin hydroxide, tebufenpyrad, pyridaben, fenpyroximate, pyrimidifen, fenazaquin,
Clofenthedine, hexthiazox, acequinosyl,
Examples include quinomethionate, phenothiocarb, ethoxazole, bifenazate and the like.

Examples of the active compounds of the nematicide include methyl isocyanate, phosthiazate, oxamyl, mesulfenphos and the like. As a bait,
For example, monofluoroacetic acid, warfarin, beartetralyl, difacine and the like can be mentioned. Active compounds for fungicides include, for example, inorganic copper, organocopper, sulfur, maneb, thiuram, thiadiazine, captan, chlorothalonil, iprovenphos, thiophanatemethyl, benomyl, thiabendazole, iprodione, procymidone, pencyclon, metalaxyl, sandphane, biletone, triflumi Examples thereof include sol, fenarimol, triforine, dithianone, triazine, fluazinam, probenazole, dietofencarb, isoprothiolane, pyroquilon, iminoctadine acetate, echromezole, dazomet, and clesoxime methyl.

As the active compound of the synergist, for example, bis
-(2,3,3,3-tetrachloropropyl) ether, N- (2-
Ethylhexyl) bisclo [2,1,1] hept-5-ene-2,3-
Examples thereof include dicarboximide and α- [2- (2-butoxyethoxy) ethoxy] -4,5-methylenedioxy-2-propyltoluene. Examples of active compounds such as herbicides include bialaphos, sethoxydim, trifluralin, mefenacet and the like. Examples of active compounds for plant regulators include indolebutyric acid, ethephon, 4-CPA and the like. Active compounds for repellents include, for example, carane-3,4-diol, N, N-diethyl-m-triamide (Deet), limonene, linalool,
Citronellal, menthol, hinokitiol, menthol, graniol, eucalyptol and the like can be mentioned.

The mode of use of the pesticidal composition of the present invention is arbitrary, and the pesticidal compound is added to the compound of the general formula (1).
For example, it is formulated into a wettable powder, a wettable powder, a water solvent, an emulsion, a liquid, a flowable such as a suspension in water or an emulsion in water, a capsule, a powder, a granule, an aerosol and the like. The content of the active ingredient compound such as the compound of the present invention in these preparations is optional, but is usually 0.001 in total amount of the active ingredient.
It is selected from the range of 1 to 99.5% by weight, and may be appropriately determined depending on various conditions such as the form of the formulation and the method of application, for example, wettable powder, wettable powder, aqueous solvent, emulsion, liquid, flowable, About 0.01 to 90% by weight, preferably 1 to 50% by weight for capsules and the like, about 0.1 to 50% by weight for powders and granules,
Preferably 1 to 10% by weight, about 0.001 to about aerosols etc.
It is preferable to manufacture the composition so as to contain about 20% by weight, preferably 0.01 to 2% by weight of the active ingredient.

The pesticide adjuvants used include, for example, a carrier (diluent), a spreading agent, and an emulsifier for the purpose of improving pest repellent effect, controlling effect, controlling effect, and improving stabilization and dispersibility. , A wetting agent, a dispersant, a disintegrant and the like can be used. Examples of the liquid carrier include water, aromatic hydrocarbons such as toluene and xylene, alcohols such as methanol, butanol and glycol, ketones such as acetone, amides such as dimethylformamide, sulfoxides such as dimethyl sulfoxide, and methylnaphthalene. Cyclohexane,
Animal and vegetable oils, fatty acids and the like can be mentioned. In addition, as a 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 emulsifiers and dispersants include ordinary surfactants, 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, a zwitterionic surfactant and 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.

For example, in the case of a water-dispersible powder, the active ingredient is mixed with the compound of the general formula (I), a solid carrier, a surfactant and the like to produce a raw powder, and the raw powder is used at a predetermined concentration. Can be diluted with water and applied. 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 can be further diluted with water to a predetermined concentration before use. it can. 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 method of use depends on the type and amount of pests,
Depending on the type of crops, trees, etc. and the cultivation form / growing state of the target, for example, arthropods, gastropods, nematodes, etc. are usually affected by these pests, Or for places where damage is expected to occur, generally 0.1 to 1000 g of active ingredient per 10 ares,
Preferably, 1 to 100 g may be applied.

Specific application methods include, for example, the above-mentioned wettable powders, wettable powders, aqueous solvents, emulsions, liquid preparations, flowable preparations such as suspensions in water and emulsions in water, capsules and the like. It may be diluted with water and sprayed on crops, trees, and the like in a range of 10 to 1000 liters per 10 ares depending on the type of target crop, trees, etc., cultivation form, and growth state. In the case of powders, granules, and aerosols, the preparations may be applied to crops, trees, and the like within the range of the use described above.

When the target pest mainly infects crops, trees, etc. in the soil, for example, wettable powder, wettable powder, aqueous solvent, emulsion, liquid, suspension in water, emulsion in water Tablets, capsules, etc., diluted with water.
It may be applied in the range of 5 to 500 liters per 10 ares. At this time, the medicine may be sprayed on the soil surface so as to be even over the entire application area, or may be irrigated into the soil. When the form of the preparation is a powder or granule, the preparation may be sprayed on the soil surface as it is so as to be uniform over the entire area to be applied. Also, when spraying or irrigation, it may be applied only around the seeds, crops, trees, etc. that you want to protect from damage by pests, or may be plowed during or after spraying to disperse the active ingredient mechanically. Good.

Further, a pesticidal composition containing the compound of the present invention as an active ingredient may be adhered to the periphery of plant seeds by a known method. By such a treatment, not only can the pests in the soil be prevented from being damaged after sowing of the seeds, but also the foliage and flowers of the plant,
Fruits and the like can also be protected from damage by pests.

When protecting the above-mentioned trees, fallen trees, processed wood, stored wood, etc. from damage by termites, beetles, etc., for example, an oil agent is applied to the surrounding soil of trees, wood, etc.
Examples of the method include spraying, injecting, irrigation, and coating an emulsion, a wettable powder, and a sol, and spraying a drug in a use form such as a powder or a granule. In such a situation, the pesticidal composition containing the compound of the present invention as an active ingredient alone or other active compounds such as insecticides, acaricides, nematicides, fungicides, repellents, synergists, etc. Can be used in combination or as a mixture.

The content of the active ingredient compound such as the compound of the present invention in these preparations is optional, but is usually 0.0001 to 95% by weight in total of the active ingredient, and 0.005 to 95% by weight in oils, powders, granules and the like. -10% by weight, and preferably 0.01-50% by weight in emulsions, wettable powders and sols. Specifically, for example, in the case of controlling and controlling termites and beetles, 0.01 to 100 g of the active ingredient compound per 1 m ² may be sprayed on soil or wood surface.

(B) Livestock Industry, Fisheries Scene, etc. The pesticidal composition containing the compound of the present invention as an active ingredient can be used internally or externally for animals such as pets bred in the livestock industry, the fishery industry and at home. Of arthropods, nematodes, flukes, tapeworms, protozoa, etc. It is effective in repelling, controlling and controlling pests, and can be used for prevention and treatment of diseases related to these pests.

The target animals include vertebrates, for example, livestock and farmed fish such as cows, sheep, goats, horses and pigs; rodents such as poultry, dogs, cats and the like, and mice, rats, hamsters and squirrels. Examples include carnivores such as ferrets, pets such as fish, and experimental animals. Among the pests, the following can be exemplified as Arthropod Insecta and Arachnida. As the diptera, for example, the family Afidae such as Yamatobu, Tsumetogebuyu, and Skabutabai; the housefly family such as blowfly, housefly and sandfly; the genus fly family such as horsefly; the genus fly family such as oxfly; the fly family such as ovine flyfly; The flies of the family Fleuridae; the flies of the flies and the flies of the flies; and the families of the flies and the mosquitoes such as Drosophila and Drosophila; the families of the mosquitoes such as the mosquitoes and the mosquitoes; Examples can be given.

Examples of the Laminoptera include fleas such as cat flea and dog flea. Examples of the lice include Liceflies, such as pig lice and bovine lice; Liceflies, such as horse lice; Liceflies, such as bovine lice; and Liceflies, such as chicken lice.

Examples of the acarids of the class Arachnida: Arachnida, Dermatophagoides farinae, Oxodid ticks, Oxodid ticks, etc .; Dermatophagoides, such as Trichoderidae; Dermatidae, such as mites; Dermatophagoids such as Dermatophagoids and Dermatophagoides mite; Dermatophagoids such as Dermatophagoides farinae and Bovine Dermatophagoids.

Examples of the nematodes of the nematode phylum include the following. Examples of the order Coleoptera include hookworms, pig nematodes, pig lungworms, ciliate nematodes, and bovine intestinal nodules. As the roundworm, for example, roundworm, roundworm of chicken, etc. can be mentioned. As for the flatworm flukes,
For example, Schistosoma japonicum, Liver Tetsu, Desertia japonicus, L. paragonimus westermani, Japanese fluke egg and the like can be mentioned.

Examples of tapeworms include foliate tapeworms, tapeworms, Beneden tapeworms, square tapeworms, striated tapeworms, and tapeworms. In the protozoan phylum flagellates, as the root flagellates, for example, Histomonas, etc., as the protoflagellate, for example, Leishmania, Trypanosoma, etc., as the polyflagellate, for example, Giardia, etc., and as the Trichomonas, For example, Trichomonas and the like can be mentioned.

Further, as the amoebices of the fleshy class, for example, Entamoeba and the like, as the spore-strain class of Piroplasma, for example, Theilaria and Babesia, and as the late-spores of the sporozoa, for example, Eimeria, Plasmodium, and Toxoplasma And the like. The pesticidal composition containing the compound of the present invention as an active ingredient is a formulation effective in the livestock industry or the fishing industry described above, and in any use form prepared by the formulation, alone or in the form of another active compound such as an insecticide , Acaricide, nematicide, fungicide, synergist, plant regulator, herbicide, poison bait, and the like. Specific examples of the other active compounds include “(A)
Agriculture, forestry scenes, etc. ", but are not limited thereto.

As a specific method of application, for example, a compounded pharmaceutical composition which can be mixed into feeds of livestock and pets or ingested appropriately, such as tablets and pills containing a pharmaceutically acceptable carrier or coating substance Orally or as a capsule, paste, gel, beverage, medicated feed, medicinal drinking water, medicated bait, sustained release large pills, other sustained release device retained in the gastrointestinal tract, or spray , Powder, grease, cream, ointment, emulsion, lotion, spot-on, pour-on, shampoo and the like.

As a method of transdermal administration or topical administration, a device (for example, a collar, a medallion, an ear tag, or the like) attached to an animal so as to control arthropods locally or systemically can also be used. Specific oral administration methods and transdermal administration methods when used as an anthelmintic for livestock and pets are shown below, but in the present invention, these administration methods are not necessarily limited to the following description.

When administered orally as a medicinal beverage preparation, the suspension is usually dissolved in a suitable non-toxic solvent or water together with a suspending agent such as bentonite, a wetting agent or other excipients. Alternatively, a dispersion may be used, and an antifoaming agent may be contained as necessary. In beverage preparations, generally the amount of the active ingredient compound is 0.01 to 1.0% by weight, preferably 0.01 to 1.0%.
0.1% by weight.

For oral administration in a dry solid unit dosage form, capsules, pills or tablets containing a predetermined amount of the active ingredient are usually employed. These forms of use are produced by homogeneously mixing the active ingredient with suitably comminuted diluents, fillers, disintegrants and / or binders such as starch, lactose, talc, magnesium stearate, vegetable gums and the like. Is done. In such a unit-use prescription, the weight and content of the anthelmintic may be appropriately set according to the type of host animal to be treated, the degree of infection, the type of parasite, and the weight of the host.

In the case of administration by feed, there may be mentioned, for example, a method in which the active ingredient compound is uniformly dispersed in the feed, a method in which the drug is used as a top dressing or a form of pellets, and the like. To achieve an antiparasitic effect, the final feed usually contains 0.0001 to 0.05% by weight of the active ingredient compound, preferably 0.0005 to 0.01% by weight.
It contains.

When dissolved or dispersed in a liquid carrier excipient, it may be administered parenterally to the animal by intragastric, intramuscular, intratracheal or subcutaneous injection. Because of parenteral administration, the active ingredient compounds are preferably mixed with vegetable oils, such as peanut oil, cottonseed oil, and the like. In such a formulation,
In general, the active ingredient compound is contained in an amount of 0.05 to 50% by weight, preferably 0.1 to 50% by weight.
0.20.2% by weight. In addition, a formulation mixed with a carrier such as dimethyl sulfoxide or a hydrocarbon solvent can be directly or topically administered to the external surface of livestock or pets by spraying or direct pouring.

(C) Public Health Scene, etc. The pest controlling agent containing the compound of the present invention as an active ingredient is
Avoidance of pests in public health situations, such as adversely affecting the food and living environment, further harming the human body, and carrying and transmitting pathogens, for maintaining public health, etc. It is also effective for extermination and control. Specifically, the pesticidal agent of the present invention is, for example, wood products such as dwelling itself, indoor and outdoor wood, wooden furniture, stored food, clothing, books, animal products (skin, wool, wool, feathers, etc.). Effective for repelling, extermination and control of lepidoptera, beetles, spots, cockroaches, flies, mites, etc., which cause damage to plant and plant products (clothing, paper, etc.) and adversely affect sanitary life It is. Specific examples of such pests in public health situations include the following.

Examples of the arthropod phylum Insecta include the following. Examples of the Lepidoptera include ascididae such as Mondriopodidae; Kalehagidae such as Kunugikarehaga; Iragidae such as Aoiraga; Madaraga such as Takenohosokuroba; Scarabaeidae such as B. And the genus Iridaceae;

As the Coleoptera, for example, the family Ceratopogonidae, such as Blue horned beetle; The beetle family, such as Mamehanmyo; The beetle family, such as Pleurotus serrata; The weevil family, such as the weevil, the weevil, the weevil, the pea weevil Beetles, such as weevil; weevil, such as weevil; beetles; Lepidoptera of the family Lepidoptera, such as Nisesemaru beetle; It can gel.

The Hymenoptera include, for example, wasp family such as wasp, ant family such as giant ant, and bee family such as pygmy beetle.
As the diptera, for example, mosquitoes such as yamato falcon; smeltaceae such as brassicae; chironaceae such as sessile chironomid; smeltaceae such as mosquitoes; flies family such as housefly; houseflies such as housefly; Etc .; Drosophilidae such as Sentid fly; Drosophilidae such as Drosophila melanogaster;
Cheese fly such as cheese fly can be mentioned.

Examples of the order Laminoptera include human fleas such as human fleas. As the order of the viscera, there may be mentioned, for example, the family Pteridomycetes, such as purple pit viper. Examples of the cockroaches include the German cockroaches such as German cockroaches and Chinese cockroaches; and the cockroaches such as American cockroaches, black cockroaches, and black cockroaches.

The Orthoptera includes, for example, Kologridae, such as Madara camphoridae and Camamadia. As the louse, for example, lice of the head lice such as head lice; lice of the lice such as lice may be mentioned. Examples of the Hemiptera include bed bugs such as bed bugs; and bugs such as bed bugs.

The termites include, for example, the termites of the termites such as the termites and termites; the termites of the termites such as the termites; the termites of the termites, such as the termites of the termites. Can be mentioned. As the spots, for example, spots such as yamatos spots and sea skewers can be mentioned.

Examples of arthropod spiders include the following. As the mites, for example, ticks such as Schurze ticks; Dermatophagoides such as house dust mites; Cyperidae such as southern mites; Lice mites such as lice mites; Dermatophagoides such as Dermatophagoides; Dermatophagoides such as Dermatophagoides;
Examples of the family include the mites of the tsutsugamushi beetle and the like; the mites of the mites such as the red mite and the mites of the scorpion beetle;

Examples of the true spiders include the spiders of the order Arachnids, such as Birch spiders; the spiders of the order Spiders, such as the spiders; the spiders of the spiders, such as the spiders and blue spiders; the spiders of the spider, such as the giant spiders;
Jumping spiders such as Miss jumping spider can be mentioned. As the scorpiones, there may be mentioned, for example, a scorpion family, such as a scorpion.

As other arthropod phylums, examples of the order Lepidoptera from the order of the order Coleoptera include those belonging to the family Coleoptera, such as Tobism and Aosum, and those belonging to the order Cestidae include, for example, the family Rabbits such as the Rabbit. Examples of the arthropod phylum, Ophiaceae include, for example, Papilionidae such as Toyakesade, and examples of the arthropod, Crustacea, include the Phytopodaceae, such as P. Furthermore, examples of the annelid fasciata include, for example, Yamaviridae such as Yamavir.

The pesticidal composition containing the compound of the present invention as an active ingredient can be used alone or in combination with other active compounds, such as insecticides, in the above-mentioned preparations effective in public health and in any use form prepared by the preparations. Miticides, nematicides,
It can be used in combination or as a mixture with fungicides, synergists, plant regulators, herbicides and poison baits. Specific examples of the other active compounds include “(A) Agriculture, forestry, etc.”
Can be listed, but the present invention is not necessarily limited to these.

The form of use of the pesticidal composition of the present invention is optional. For example, when protecting the above-mentioned animal products and plant products, it is necessary to spray oils, emulsions, wettable powders, powders, etc. Can be controlled by methods such as installation of smokers and aerosols, installation of granules, tablets and poison baits, and spraying of aerosols. The amount of the active ingredient compound in these preparations is preferably 0.0001 to 95% by weight.

As a method of application, for pests, for example, arthropods that cause direct harm or arthropods that are vectors of disease, etc., they may be surrounded by potential agents such as oils, emulsions, Spraying / injection / irrigation / application of wettable powders, spraying powders, etc., fumigants, heated aerosols such as mosquito coils, self-burning type smokers, chemical reaction type aerosols, smokers such as fogging,
A method of treating with a preparation such as a ULV agent can be used. They may be applied in other forms such as granules, tablets or poison bait, or by dripping floating powder, granules, etc. into waterways, wells, reservoirs, water tanks and other running or stationary water. I just need.

Further, with respect to mites, which are also pests in agriculture and forestry, “(A) Agriculture, forestry scene, etc.”
Can be controlled by the same method as described in the section, and for flies and the like, a method in which the active ingredient is mixed in feces by mixing in livestock feed, and mosquitoes It is also effective to volatilize the air with an electric mosquito trap.

The formulations in these forms of use are present as a mixture with other active compounds as described above, for example, insecticides, acaricides, nematicides, fungicides, repellents or synergists. It is also preferable that these preparations contain the active ingredient compound in a total amount of 0.0001 to 95% by weight. In addition, it is also possible to use together with other active compounds at the time of use.

When protecting houses and wooden furniture from damage by termites or beetles, for example, spraying, injecting, irrigation, and applying oils, emulsions, wettable powders, and sols to and around them. , Powders, granules and the like, and a method of spraying the medicine in the form of use. In such a situation, the compound of the present invention alone or other active compounds,
For example, it can be used in combination or as a mixture with insecticides, acaricides, nematicides, fungicides, repellents, synergists and the like.

The content of the active ingredient compound such as the compound of the present invention in these preparations is optional, but is usually 0.0001 to 95% by weight in total of the active ingredient, and 0.005 to 95% by weight for oils, powders, granules and the like. -10% by weight, and preferably 0.01-50% by weight in emulsions, wettable powders and sols. Specifically, for example, in the case of controlling and controlling termites and beetles, 0.01 to 100 g of the active ingredient compound per 1 m ² may be sprayed on the periphery or directly on the surface.

When repelling, exterminating or controlling pests, such as causing harm to the human body or carrying or transmitting pathogens,
In addition to the above, suitable ingestible pharmaceutical compositions such as tablets, pills, capsules, pastes, gels, drinks, medicinal feeds, medicinal products containing pharmaceutically acceptable carriers and coating materials, Oral administration, such as drinking water, medicated bait, sustained release large pills, and other sustained release devices kept in the gastrointestinal tract, or spray, powder,
It can be transdermally administered as grease, cream, ointment, emulsion, lotion, spot-on, pour-on, shampoo, and the like. Specific pharmaceutical formulations are described in “(B) Livestock Industry,
The formulation can be carried out in the same manner as in the method described in the section "Scenery in the fishing industry".

[0084]

EXAMPLES The present invention will be described in more detail with reference to the following Examples, but it should not be construed that the present invention is limited to the following Examples without departing from the scope of the invention. (Example 1) 1- (2,6-dichloro-4-trifluoromethylphenyl) -4-trifluoromethyl-5-
(Pyrazin-2-ylmethylamino) pyrazole-3-
Production of carbonitrile

[0085]

Embedded image

5-Amino-1- (2,6-dichloro-4
-Trifluoromethylphenyl) -4-trifluoromethylpyrazole-3-carbonitrile (1.9 g), p-toluenesulfonic acid monohydrate (60 mg) was added to a mixture of formylpyrazine (0.56 g) and toluene (10 ml), and the generated water was removed. The mixture was refluxed for 1 hour while heating. After cooling to room temperature, the solvent was evaporated under reduced pressure to give crude 1- (2,6-dichloro-4-trifluoromethylphenyl) -4-trifluoromethyl-5-
(Pyrazin-2-ylmethylideneimino) pyrazole-
3-carbonitrile was obtained.

The 1- (2,6-dichloro-4- obtained above)
To a solution of trifluoromethylphenyl) -4-trifluoromethyl-5- (pyrazin-2-ylmethylideneimino) pyrazole-3-carbonitrile in 5 ml of ethanol was slowly added 0.29 g of sodium borohydride. After stirring at room temperature for 1 hour, the mixture was poured into ice water, and concentrated hydrochloric acid was added until the mixture became acidic. Ethyl acetate was added and extracted. The organic phase was washed with saturated saline and dried over anhydrous sodium sulfate. The residue is purified by silica gel column chromatography,
2.0 g were obtained. Melting point 152-153 ° C ¹ H NMR (CDCl ₃ ): 4.42 (2H, d), 5.50 (1H, t), 7.79 (2H, s),
8.38 (1H, t), 8.52 (2H, d) (Example 2) 1- (2,6-dichloro-4-trifluoromethylphenyl) -4-iodo-5- (pyrazine-
Preparation of 2-ylmethylamino) pyrazole-3-carbonitrile

[0088]

Embedded image

5-Amino-1- (2,6-dichloro-4
-Trifluoromethylphenyl) -4-iodopyrazole-3-carbonitrile 1.0 g, formylpyrazine 0.24 g
Then, 28 mg of p-toluenesulfonic acid monohydrate was added to a mixture of 10 ml of toluene and toluene, and the mixture was heated under reflux for 1 hour while removing generated water. After cooling to room temperature, the solvent was evaporated under reduced pressure to give crude 1- (2,6-dichloro-4-trifluoromethylphenyl) -4-iodo-5- (pyrazin-2-ylmethylideneimino) pyrazole-3. -Carbonitrile was obtained.

The obtained 1- (2,6-dichloro-4-)
To a solution of trifluoromethylphenyl) -4-trifluoromethyl-5- (pyrazin-2-ylmethylideneimino) pyrazole-3-carbonitrile in 5 ml of ethanol, 0.11 g of sodium borohydride was gradually added. After stirring at room temperature for 1 hour, the mixture was poured into ice water, and concentrated hydrochloric acid was added until the mixture became acidic. Ethyl acetate was added and extracted. The organic phase was washed with saturated saline and dried over anhydrous sodium sulfate. The residue is purified by silica gel column chromatography,
0.9 g was obtained. Melting point 101-103 ° C ¹ H NMR (CDCl ₃ ): 4.45 (2H, d), 4.75 (1 H, b), 7.75 (2H, d),
8.41 (1H, t), 8.50 (2H, d) <Formulation Example 1> Water dispersant 20 parts by weight of the compound of the present invention, Carplex # 80 (white carbon, Shionogi & Co., Ltd., trade name) 20 parts by weight, ST kaolin clay (Kaolinite, Tsuchiya Kaolin Co., Ltd., 52 parts by weight), Solpol 9047K (anionic surfactant, Toho Chemical Co., Ltd., 5 parts by weight), Lunox P65L (anionic surfactant, Toho Chemical) (Trade name) 3 parts by weight were blended and 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,
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 was 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 surfactant). Mixture, 15 parts by weight of Toho Chemical Co., Ltd.), and 20% by weight of the 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 Sorbone 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 mixed and pulverized with 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 flowable agent was obtained.

Hereinafter, test examples of agricultural and horticultural insecticides 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 moth larvae A cut cabbage leaf (diameter 6 cm) was immersed in a water dilution of the agricultural and horticultural insecticide of the present invention produced according to the formulation of Formulation Example 1 for 1 minute. After immersion, air-dry the plastic cup (7
cm), and five third instar larvae of the Japanese moth were released into the cup (500 ppm, 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 writhing, and the writhing larvae were killed by 頭 to determine the mortality (%). Compound 1 of the present invention showed a 100% mortality.

Test Example 2: Insecticidal effect on the larvae of Spodoptera litura The cabbage cut leaves (diameter 6 cm) were immersed in a water dilution of the agricultural and horticultural insecticide of the present invention prepared according to the formulation of Preparation Example 1 for 1 minute. After immersion, air-dry the plastic cup (7
In this cup, five third-instar larvae of Spodoptera litura were released (500 ppm, 2 repetitions). After being kept in a constant temperature room at 25 ° C, 5 days after release, the larvae were examined for life and death and agony,
The insecticidal rate (%) was determined by assuming that the writhing insect was １ ／ dead. Compound 1 of the present invention showed a 100% mortality.

Test Example 3: Insecticidal effect of adzuki beetle on adult insect Red bean 2 on a glass cylinder (inner diameter 3 cm x length 15 cm)
Individually, 10 adults of Azuki weevil were released. Formulation Example 3
0.3 ml of a water dilution of the agricultural and horticultural insecticide of the present invention prepared according to the above formula was sprayed onto the above-mentioned glass cylinder using a spray tower (manufactured by Mizuho Rika) (500 ppm, 2 repetitions). The larvae were kept in a constant temperature room at 25 ° C., and after 4 days from the treatment, the larvae were examined for viability and agony, and the killing rate (%) was determined by assuming that the agony worms were 死 dead. Compound 1 of the present invention showed a 100% mortality.

Test Example 4: Pesticidal effect of peach aphid on larvae The petiole of a radish leaf was inserted into a screw bottle (capacity: 10 ml) containing water, and peach peach aphid was applied per leaf.
Five to six animals were inoculated. After inoculation, glass cylinder (diameter: 0.5c
m, height: 15 cm, with a mesh lid) and aphids were grown in a thermostat at 25 ° C. for 3 days. After removing the aphid adults from the radish leaves, the leaves were immersed (about 5 seconds) in a water dilution of the agricultural and horticultural insecticide of the present invention manufactured according to the formulation of Formulation Example 3 and returned to the glass cylinder ( 500 ppm, 2 repetitions). It was kept in a constant temperature room at 25 ° C., and on the fourth day after the treatment, the number of aphids on radish leaves was examined, and the insecticidal rate (%) was determined based on the results. Compound 1 of the present invention showed a 100% mortality.

[0097]

The 1-aryl-3-cyano-5 of the present invention
-A heteroarylalkylaminopyrazole derivative,
It is excellent as an insecticidal effect and has a wide insecticidal spectrum, and is useful as a novel pesticide.

Claims (7)

[Claims] 1. A 1-aryl-3-cyano-5-heteroarylalkylaminopyrazole derivative represented by the following general formula (1). Embedded image (In the above formula, X represents N or C-halogen, R ¹ represents a haloalkyl group or a halogen atom, R ² represents a hydrogen atom, an alkyl group or an acyl group, and R ³ represents a hydrogen atom or an alkyl group. , A is any group represented by A-1 to A-4 above, R ⁴ represents a hydrogen atom, an alkyl group, or a halogen atom, and m and n represent 0 or 1. 2. The 1-aryl-3-cyano-5-heteroarylalkylaminopyrazole derivative according to claim 1, wherein A is A-1 and R ⁴ represents a hydrogen atom or an alkyl group. . 3. The 1-aryl-3-cyano-5-heteroarylalkylaminopyrazole derivative according to claim 1, wherein R ¹ is a haloalkyl group having 1 to 4 carbon atoms. 4. The 1-aryl-3-cyano-5-heteroarylalkylaminopyrazole derivative according to claim 1, wherein R ¹ is a haloalkyl group having 1 to 2 carbon atoms. . 5. 1- (2,6-dichloro-4-trifluoromethylphenyl) -4-trifluoromethyl-5
(Pyrazin-2-ylmethylamino) pyrazole-3-
Carbonitrile 6. The method according to claim 1, wherein
A pest control agent comprising an aryl-3-cyano-5-heteroarylalkylaminopyrazole derivative as an active ingredient. 7. The method according to claim 1, wherein
An insecticide comprising an aryl-3-cyano-5-heteroarylalkylaminopyrazole derivative as an active ingredient.