JP2002121191A - Pyrazole derivative, noxious organism controlling agent containing the same as active ingredient and method of producing the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a novel noxious organism-controlling agent the has both of a wide range of insecticidal spectrum and excellent insecticidal activity with systemic transition activity and high safety. SOLUTION: The objective compound is 1-aryl-3-cyano-5-pyridylalkyl- aminopyrazole derivative represented by following general formula (1) [X is N or C-halogen atom; R1 is a halo-alkyl (perhaloalkyls are excluded); R2 is H or an alkyl; R3 is H, an alkyl or an acyl; R4 is H, hydroxy, an alkyl, a haloalkyl, an alkoxy, a haloalkoxy, an alkylthio, an alkyl-sulfinyl, an alkylsulfonyl, a halogen atom, nitro or cyano].

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

[0001] The present invention relates to a novel 1-aryl-3-cyano-5-pyridylalkylaminopyrazole derivative and a pesticide, particularly an insecticide, containing the derivative 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 overcomes these problems. JP-A-10-338676 discloses a novel 1-aryl-3-cyano-5-heteroarylalkylaminopyrazole derivative as a highly safe compound.

[0004]

However, the compounds described in Japanese Patent Application Laid-Open No. 10-338676, etc., are superior in insecticidal activity and reduced in toxicity as compared with known compounds, but have a view of permeation transfer activity. In addition, it has been found that those having poor performance or having high permeation transfer activity have relatively insufficient safety. The osmotic transfer activity is an important factor in terms of increasing the efficiency of a method of applying a chemical in controlling pests, and applying the method to a soil treatment / medicating method that is particularly effective in controlling pests such as sucking insect pests. In recent years, there has been an increasing demand for safety for living organisms and the environment other than target pests, and furthermore, environmental protection measures will be strengthened in the future. Therefore, in view of these facts, it is also important to find a compound with higher safety in order to develop a pesticide suitable for stricter regulations.

[0005]

The present inventors have made intensive efforts to solve the above-mentioned problems, and as a result, have found that 1-aryl-
In a 3-cyano-5-heteroarylalkylaminopyrazole derivative, a specific aryloxypyridyl group in which the heteroaryl group bonded to the alkylamino group at the 5-position of the pyrazole ring is further substituted with a pyridyl group and the substituent at the 4-position of the pyrazole ring is partially halogenated By using an alkylthio group, it has been found that a compound having improved safety in permeation transfer and high safety can be obtained, and the present invention has been completed.

That is, the gist of the present invention is the following general formula (1)

[0007]

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(In the above formula, X represents an N or C-halogen atom, R ¹ represents a haloalkyl group (excluding a perhaloalkyl group), R ² represents a hydrogen atom or an alkyl group, and R ³ represents a hydrogen atom or an alkyl group. R ⁴ represents a hydrogen atom, a hydroxyl group, an alkyl group, a haloalkyl group, an alkoxy group, a haloalkoxy group, an alkylthio group, an alkylsulfinyl group, an alkylsulfonyl group, a halogen atom, a nitro group or a cyano group; Represents a group.)
A 1-aryl-3-cyano-5-pyridylalkylaminopyrazole derivative represented by the formula (I), a pesticidal agent containing the same as an active ingredient, and a method for producing the compound. Hereinafter, the present invention will be described in detail.

[0009]

BEST MODE FOR CARRYING OUT THE INVENTION In the present invention, the substituent R ¹ in the compound represented by the above general formula (1) is a fluoromethyl group, a difluoromethyl group, a 2-fluoroethyl group, a 2-chloroethyl group, 2,2,2-trifluoroethyl group, 2,2,2-trichloroethyl group, 3-chloropropyl group, 3-bromopropyl group, 3,3,3-trifluoropropyl group, 2,2,3,3 -Tetrafluoropropyl, 2,2,3,3,3-pentafluoropropyl, 2,2-dichloro-3,3,3-trifluoropropyl, 2,2-dichloro-3,3,3- Trifluoropropyl group, 3,3,3-trichloropropyl group,
A straight-chain or branched-chain alkyl group partially halogenated such as a 4-chlorobutyl group, a 4,4,4-trifluorobutyl group, a 3,3,4,4,4-pentafluorobutyl group, etc. . Of these, a haloalkyl group having 1 to 4 carbon atoms is preferable, and a haloalkyl group having 1 to 2 carbon atoms such as a fluoromethyl group and a difluoromethyl group is particularly preferable.

R ² is a hydrogen atom; or a linear or branched alkyl such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl and t-butyl. Represents a group. Of these, a hydrogen atom or an alkyl group having 1 to 4 carbon atoms is preferable, and a hydrogen atom is particularly preferable. R ³ is a hydrogen atom; a linear or branched alkyl group such as a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a sec-butyl group, a t-butyl group; Methylcarbonyl group, ethylcarbonyl group,
n-propylcarbonyl group, isopropylcarbonyl group, n-butylcarbonyl group, isobutylcarbonyl group, sec-butylcarbonyl group, represents a straight-chain or branched-chain acyl group such as t-butylcarbonyl group, as the above alkyl group or acyl group Preferably has 1 to 4 carbon atoms. R ³ is particularly preferably a hydrogen atom.

R ⁴ is a hydrogen atom; a hydroxyl group; a linear or branched chain such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group and a t-butyl group. Alkyl group; difluoromethyl group, trifluoromethyl group, 2-fluoroethyl group, 2
-Chloroethyl group, 2,2,2-trifluoroethyl group, 2,2,2-trichloroethyl group, 3-chloropropyl group, 3-bromopropyl group, 3,3,3-trifluoropropyl group, 2, 2,3,3-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, 3,3,3-trichloropropyl, 4-chlorobutyl, 4,4,4-trifluorobutyl, 3,
Straight-chain or branched-chain haloalkyl groups such as 3,4,4,4-pentafluorobutyl group; methoxy group, ethoxy group,
linear or branched chain alkoxy groups such as n-propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, sec-butoxy group, t-butoxy group; difluoromethoxy group, trifluoromethoxy group, 2-fluoroethoxy group , 2-chloroethoxy, 2,2,2-trifluoroethoxy, 2,2,2-trichloroethoxy, 3-chloropropoxy, 3-bromopropoxy, 3,3,3-trifluoropropoxy 2,2,
3,3-tetrafluoropropoxy group, 2,2,3,
3,3-pentafluoropropoxy group, 2,2-dichloro-3,3,3-trifluoropropoxy group, 2,2-
Dichloro-3,3,3-trifluoropropoxy group,
1,3-difluoro-2-propoxy group, 1,1,1,
3,3,3-hexafluoro-2-propoxy group, 3,
3,3-trichloropropoxy group, 4-chlorobutoxy group, 4,4,4-trifluorobutoxy group, 3,3,
Straight-chain or branched-chain haloalkoxy groups such as 4,4,4-pentafluorobutoxy group; methylthio group, ethylthio group, n-propylthio group, isopropylthio group, n-butylthio group, isobutylthio group, sec-butylthio group, straight-chain or branched-chain alkylthio groups such as t-butylthio group; methylsulfinyl group, ethylsulfinyl group, n-propylsulfinyl group, isopropylsulfinyl group, n-butylsulfinyl group, isobutylsulfinyl group, sec-butylsulfinyl group, t- Linear or branched alkylsulfinyl group such as butylsulfinyl group; methylsulfonyl group, ethylsulfonyl group, n-propylsulfonyl group, isopropylsulfonyl group, n-butylsulfonyl group, isobutylsulfonyl group, sec-butylsulfonyl group A straight-chain or branched-chain alkylsulfonyl group such as a t-butylsulfonyl group; a halogen atom such as a chlorine atom, a fluorine atom or a bromine atom; a nitro group or a cyano group;
The haloalkyl group, alkoxy group, haloalkoxy group, alkylthio group, alkylsulfinyl group and alkylsulfonyl group preferably have 1 to 4 carbon atoms. Particularly, R ⁴ is preferably a hydrogen atom or an alkyl group, and most preferably a hydrogen atom.

In the above-mentioned compound of the general formula (1),
Compounds obtained by combining preferred substituents for R ^{1 to} R ⁴ are more preferred compounds. Preferred combinations of the substituents include, for example, R ¹ is a partially halogenated alkyl group having 1 to 2 carbon atoms, and R ² , R ³ and R
^And compounds in which ⁴ is a hydrogen atom. In particular, those in which R ¹ is a fluoromethyl group or a difluoromethyl group have high insecticidal activity when used as an active ingredient of a pesticide, particularly an insecticide (that is, a sufficient insecticidal activity even at a low dose). The most preferred compound is 1- (2,6-dichloro-4-trifluoromethylphenyl) -4-difluoromethylthio-5- (pyridin-2-ylmethylamino) as shown below. ) Pyrazole-3-carbonitrile.

[0013]

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As a method for producing the compound of the present invention represented by the general formula (1), the production method described in JP-A-10-338676 can be used. Other preferred examples include the methods represented by the following Reaction Formulas-1 to 4.

[0015]

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(In the above formula, R ¹ , R ² , R ³ , R ⁴ and X are as described above.) In the reaction formula 1, R ¹ S is added to the pyrazole derivative of the general formula (2).
X ¹ (wherein R ¹ has the same meaning as in general formula (1), and X ¹ represents a chlorine atom, a bromine atom, an alkylsulfonyl group or an arylsulfonyl group). 1 shows a method for producing a pyrazole derivative.
X ¹ is preferably a chlorine atom. Specific examples of R ¹ SX ¹ include difluoromethylsulfenyl chloride (CH
F ₂ SCl), which is described in J. Org. Chem., Vo.
l.44, No. 10, 1708 (1979).

In this reaction, R ₁ SX ₁ is used in an amount of 0.5 to 10.0 molar equivalents, preferably 0.8 to 5 molar equivalents, relative to the compound represented by the general formula (2), and 0 ° C. ~ 15
The reaction is carried out at 0 ° C., preferably 0 ° C. to 100 ° C., and is generally carried out for 1 hour to 24 hours, preferably 1 to 4 hours, depending on the reaction scale. Solvents used in this reaction include aromatic hydrocarbons such as benzene, toluene and xylene; ketones such as acetone and methyl ethyl ketone; halogenated hydrocarbons such as chloroform and methylene chloride; ether solvents such as ether, diisopropyl ether and tetrahydrofuran Aprotic polar solvents such as N, N-dimethylformamide (DMF) and dimethylsulfoxide; among them, toluene and dichloromethane are preferred.

The reaction is preferably carried out in the presence of a base, and as the base, amines such as pyridine and triethylamine are used. Reaction formula 2 shows a method for producing a pyrazole derivative of the general formula (1), wherein a haloalkylating agent is allowed to act on the pyrazole derivative of the general formula (3). Examples of the haloalkylating agent used in this reaction include fluoromethyl bromide, difluoromethyl chloride, trimethylsilyldifluoromethane and the like.

Examples of the solvent used in this reaction include ether solvents such as tetrahydrofuran, diethyl ether and dimethoxyethane; hydrocarbon solvents such as toluene and hexane; and halogenated hydrocarbon solvents such as dichloromethane and chloroform. Is preferred. In this reaction, a haloalkylating agent is used in an amount of 0.5 to 10.0 molar equivalents, preferably 0.8 to 5 molar equivalents, based on the compound represented by the general formula (3), and the reaction is carried out at -20 ° C to The reaction is carried out at 120 ° C., preferably in the range of 0 ° C. to room temperature, and is generally carried out for 1 hour to 24 hours, preferably 1 to 4 hours, depending on the reaction scale.

Reaction Scheme 3 shows a method for producing a pyrazole derivative of the general formula (1), which comprises reacting a pyrazole derivative of the general formula (4) with a haloalkylating agent. As the haloalkylating agent, a haloalkylating agent having a halomethyl group is preferably exemplified. As the haloalkylating agent having a halomethyl group, a compound having a difluoromethyl group is preferably exemplified, and more preferably, a compound known as a difluorocarbene precursor is exemplified. Sprin as difluorocarbene precursor
ger, Published by Hiyama, Organofluorine compounds, p10
Compounds described in 7-111 are exemplified, and specific examples thereof include difluoromethyl chloride, chlorodifluoroacetic acid, metal salts of chlorodifluoroacetic acid, and chlorodifluoroacetic acid esters. Solvents used in this reaction include N, N-dimethylformamide (DMF), dimethylsulfoxide (D
Aprotic polar solvents such as MSO); alcoholic solvents such as methanol, ethanol and isopropanol;
Hydrocarbon solvents such as toluene and hexane; halogenated hydrocarbon solvents such as dichloromethane and chloroform; basic solvents such as triethylamine and liquid ammonia; and polar solvents such as DMF and alcoholic solvents such as ethanol and isopropanol. Is preferred.

The reaction is carried out at -20 ° C to 200 ° C, preferably at 0 ° C.
C. to 150.degree. C., for 1 to 24 hours, preferably 1 to 4 hours. In addition, this reaction
It can also be performed in a layer system. In such a case, examples of the solvent include a two-layer system of a polar solvent such as dioxane, a hydrocarbon solvent such as toluene and xylene, and a concentrated aqueous sodium hydroxide solution. The reaction is carried out at a temperature in the range of −20 ° C. to 120 ° C., preferably 0 ° C. to room temperature, and generally 1 hour to 24 hours, preferably 1 hour to 24 hours, depending on the reaction scale.
Performed in 4 hours.

The method of Reaction Scheme 4 shows a method for producing a pyrazole derivative of the general formula (1), which comprises reacting a pyrazole derivative of the general formula (5) with a haloalkylating agent. In this reaction, the reaction is performed in the presence of a reducing agent, if necessary. Examples of the reducing agent include hydrides such as sodium borohydride, zinc borohydride, lithium aluminum hydride, metallic zinc, and hydrazine. The amount used is 1 to 20 times the molar amount of the substrate,
Preferably, the reaction is performed in a range of 1 to 5 moles. Other reagents and conditions to be used are the same as those described for the general formula (3).

The compound of the general formula (3), (4) or (5) can be produced by a known method using the compound of the general formula (2) as a raw material. The most preferred compound of the compounds of the present invention, 1- (2,6-dichloro-
In the case of 4-trifluoromethylphenyl) -4-difluoromethylthio-5- (pyridin-2-ylmethylamino) pyrazole-3-carbonitrile, a particularly preferred production method is shown in Reaction Formula 1 'or Reaction Formula 4'. Route.

[0024]

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Next, a method for producing the pyrazole derivative represented by the general formula (2) will be described. There are the following two methods for producing the pyrazole derivative represented by the general formula (2). 1) A method for converting a side chain of a pyrazole derivative 2) A method for obtaining a target product while synthesizing a pyrazole skeleton In a method for converting a side chain of a pyrazole derivative in 1), a generally known method for producing an amine (for example, Orga
nic Functional Group Preparations I, p377, chapter
13 (Amines), Academic Press, 1983). Specifically, general formula (6) and general formula (7)
Alternatively, a pyrazole derivative represented by General Formula (2) can be produced by a method represented by Reaction Formula 5-8 using a compound represented by General Formula (8) as a raw material.

[0026]

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(In the above reaction formula, X, R ² , R ³ and R
⁴ has the same meaning as in formula (1). X ⁵ represents a leaving group such as a halogen atom or a hydroxyl group; X ⁶ represents a halogen atom, a hydroxyl group or an alkoxy group; and A represents an R ⁴ -pyridyl group. )

The condensation reaction in the above reaction scheme can be carried out according to a known method.
Further, as the reducing agent used in the reduction reaction, ordinary imine,
Reagents used for the reduction reaction of amide and haloimidate can be used, and hydrogen or a hydrogen donor is used.
When using hydrogen, a catalyst such as palladium or platinum is usually used. Examples of the hydrogen donor include an organic hydrogen donor such as formic acid and isopropanol; an inorganic hydrogen donor such as hydrazine; and a metal hydride. Examples of the metal hydride include borane THF complex, sodium borohydride, sodium cyanoborohydride, lithium borohydride, and lithium aluminum hydride. In the case of reaction formula 8, a so-called reductive amination reaction in which a) formation of an imine compound (10) and b) formation of a pyrazole derivative (2) by reduction are performed in the same step is also effective.

Examples of the solvent used in this reaction include ethers such as diethyl ether, dioxane and tetrahydrofuran; and polar solvents such as alcohols such as methanol, 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. Solvents used in this reaction include non-polar solvents such as benzene, toluene and xylene; carbon tetrachloride,
Halogen-based solvents such as chloroform and dichloromethane; and ether-based 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. As a method of obtaining the target product while synthesizing the pyrazole skeleton of 2), JP-A-10-
Although various general methods are described in 338676, the method shown in Reaction formula 9 is preferable.

[0032]

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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, the agricultural, forestry, livestock, and fisheries industries, product preservation scenes in these industries and public It is effective for repelling pests, controlling and controlling pests in a wide range of situations such as sanitation. In particular, the compound of the present invention is used in agriculture, forestry, and the like, specifically, when cultivating crops, and in repelling, controlling, and controlling pests that damage the crops, trees, ornamental plants, and the like, and in public health situations. It exerts an excellent effect as an insecticide or acaricide used for such purposes.

The specific use scene, target pest,
Although the method of use and the like are shown, the present invention is not limited to the following description. More specifically, the pests are not limited to target pests, and the pests include adults, larvae, eggs, and the like. (A) Agriculture, forestry scenes, etc .; Pest control agents containing the compound of the present invention as an active ingredient include agricultural crops such as food crops (rice, wheat, 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 cause damage to plants and ornamental plants (herbs, flowers, garden trees, etc.) It is valid. Furthermore, 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 arthropod phylum insects include the following. As Lepidoptera, for example, Noctuidae such as Lotus armyworm, Helicoverpa armigera, Artemisia moth, Tamanagininuwaba, etc .;
Anthophoridae such as Anopheles japonicus and Papilio persicae; Aminidae such as Mina moga; Scarletidae, such as peach sink moth; Singing moth, such as peach sink moth; Iraga, such as iraga; Lycaenidae of the family; Paeoniaceae, such as Artemisia japonica; It can gel.

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

As the Hemiptera, for example, stink bugs such as chafered stink bugs and sting bugs; sting bugs such as pear stink bugs; helicopterids such as pygmy beetles; sting bugs such as spider helicopter; sting bugs; 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; the leafhoppers, such as the leafhopper leafhopper; Phylloceraceae such as Krya aphid; Aphids such as apple aphid; Aphids such as cotton aphid, peach aphid, okabonoa aphid; And the like; and Pterodactylidae, such as pear and round insects.

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

As the diptera, for example, the flies of soybean flies, such as soybean flies; the families of fruit flies, such as the fruit flies; 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, a bug family, such as a beetle; and a family of bugs, such as a pine beetle. 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 Oxodidae, such as Okadan-nagaushi. As the spider mites of the order of the Arachnida, for example, Dermatidae such as Dermatophagoid mite and Cyclamenidae;
Red mite, such as wheat mite; Red mite, such as grape spider mite; Red mite, such as red mite, Kanzawa spider mite, red mite, apple spider mite; it can.

The mollusc phylum Gastropods include, for example, the midgastropods of the gastropods, such as the scallop apple, and the stalked eyes such as African snails, slugs, slugs, slugs, and scabies. be able to. The following can be exemplified as the nematode phylum and the tail line. Examples of the genus Pteratophyta include, for example, Anguinaceae, such as Imogusa nematode; Tilenkorinkusu, such as Namiikusu nematode; Platylenex, such as Kitanegusaresuenchi, Minaminegusaresenchuu; 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.

As the order of the genus Nematoda, there may be mentioned, for example, Longiduraceae, such as the genus Nematoda; Further, the compound of the present invention is also effective for repelling, controlling and controlling pests that damage trees or affect the vigor of 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; Kagayaga etc .; A mothitibidae family such as A. americana; a motritibaceae family such as a shiimoglitiviga;

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

The Hemiptera includes, for example, aphid family such as Aphid aphid; mosquito aphid family such as Scotch mosquitoes; Examples of the Hymenoptera include honeybees such as Larch red wasp, etc .; honeybees such as pine wood wasp, etc .;

Examples of the order Diptera include the family Amaryllidaceae, such as the scutellidae; the flies, such as L. japonicus; and the flies, e.g. Examples of the spiders of the order Arachnida include spider mites and spider mites.

Examples of the nematodes of the order Nematoda: Parasitaferenidae such as the pine wood nematode can be mentioned. 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 preparations effective in agriculture and forestry, and in any use form prepared by the preparations. 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 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,
Methidathion, salicion, acephate, dimeton-S
Methyl, disulfotone, monocrotophos, azinephosmesyl, parathion, hosalone, pirimiphosmethyl, prothiophos and the like can be mentioned. Examples of the carbamate include metorcarb, fenobucarb, propoxur, carbaryl, ethiophencarb, 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, dinotefuran, thiamethoxam, thiacloprid, clothianidin 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 juvenile hormone agents include, for example, 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, pyridalyl and the like. Active compounds for miticides include, for example, dicophor, phenisobromolate, benzomate, tetradiphone, polynactin complex, amitraz, propargyl, fenbutatin oxide,
Tricyclohexyltin hydroxide, tebufenpyrad, pyridaben, fenpyroximate, pyrimidifen, phenazaquin, clofenthedine, hexthiazox, acequinosyl, quinomethionate, phenothiocarb, ethoxazole, bifenazate, fluacripyrim and the like can be mentioned.

Examples of the nematicide active compound include methyl isocyanate, phosthiazate, oxamyl, mesulfenphos, cadusaphos and the like. As bait, for example, monofluoroacetic acid, warfarin,
Coumatetralyl, 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, sandphan, biletone, triflumi Zol, fenarimol, triforine, dithianon, triazine, fluazinam, probenazole, dietofencarb, isoprothiolane, pyrochylone, iminoctadine acetate, eclomethol, dazomet, clesoxime methyl, carpropamide, diclosimet, tricyclazole, probenazole, ipconazole, azoxystrobin, azoxystrobin S-methyl, phenoxanil, code number NNF-98 Compounds represented by 50 (Nippon Agrochemical Co., Ltd.), compounds represented by code number BJL-003 (BASF), compounds represented by code number DF-391 (Dainippon Ink Co., Ltd.) and the like. be able to.

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 of the repellent 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 form 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 used as a formulation in wettable powders, wettable powders, aqueous solvents, emulsions, solutions, flowables such as suspensions in water and emulsions in water, capsules, powders, granules, aerosols 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 a formulation form, an application method, etc., for example, a wettable powder, a wettable powder, a water solvent, an emulsion, a liquid, a 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, improving stabilization and dispersibility, and the like. , A wetting agent, a dispersant, a disintegrant and the like can be used. As the liquid carrier, water, toluene, aromatic hydrocarbons such as xylene, methanol, butanol, alcohols such as glycol, ketones such as acetone, amides such as dimethylformamide, sulfoxides such as dimethylsulfoxide, methylnaphthalene, Cyclohexane,
Animal and vegetable oils, fatty acids and the like can be mentioned. As solid carriers, 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. 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 wettable powder, the active ingredient is mixed with a 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, a stock solution emulsion can be prepared by mixing a solvent, a surfactant and the like with the above-mentioned compound of the active ingredient, and this stock solution can be further diluted with water to a predetermined concentration before use. it can. In the case of powder, the compound of the active ingredient and the solid carrier can be mixed and applied as it is, and in the case of granules, 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 / growth 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, capsule preparations and the like. It may be diluted with water and sprayed on crops, trees, etc. in the range of 10 to 1000 liters per 10 ares depending on the type of target crops, 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 in the range of the above-mentioned methods of use.

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. In addition, when spraying or irrigation, it may be applied only around seeds, crops, trees, etc. which are desired to be protected from damage by pests. Good.

By using the compound of the present invention for coating seeds and sowing it, the occurrence of pests can be suppressed for a long period of time. As a specific method, a wettable powder, a sol and a powder prepared by containing the compound of the present invention are coated around the moistened seed. At that time, seed 1
In general, the amount of the wettable powder, the sol or the powder is preferably 1 to 1000 g, more preferably 10 to 200 g, based on 00 g. By sowing the coated seeds created in this way, not only can not only prevent damage by pests in the soil, but also, after growth, the foliage and flowers of plants, fruits, etc. It can also protect you from damage. Examples of the method of using the compound of the present invention at the time of sowing include the following methods. The granules containing the compound of the invention are mixed with the seeding soil and the soil is placed in a nursery. At this time, the soil to which the granules have been applied may be used only for the bed soil of the nursery bed, the soil to which the granules have been applied may be used only for the cover soil of the nursery box, or the bed soil and the cover soil may be used. You may use for both. In this case, it is generally preferable that the amount of the granules is 0.1 to 100 g, more preferably 1 to 50 g, based on 1.0 kg of soil. Alternatively, the method may be such that, after placing the bed soil in a nursery bed, the granules containing the compound of the present invention are sprayed around the seeded area, or the soil is spread after sowing and then the granules are sprayed. . In this case, it is generally preferable that the amount of the granule is 1 to 1000 g, more preferably 10 to 100 g, per one seedling raising box (normally, one seedling raising box is 0.5 a at the time of planting). . In addition, you may use a wettable powder, a powder, etc. by a similar application method instead of a granule.

Further, as a method of using the compound of the present invention as a box application agent during the period from germination to planting (greening stage) or at the time of transplantation, the following methods are exemplified. A granule containing the compound of the present invention is applied to a nursery box by granulation. In general, the amount of the granule is preferably 1 to 1000 g, and more preferably 10 to 100 g, per one seedling raising box (normally, one seedling raising box is 0.5a at the time of planting).

In the case of emulsions, liquids or sols (flowables), or microcapsules containing the compound of the present invention, wettable powders, wettable powders, aqueous solvents are used as they are or diluted with water. In the case of a granular water solvent, it may be diluted with water and subjected to irrigation in a nursery box. In this case, in general, the treatment amount is preferably 1 to 1000 ml, more preferably 10 to 100 ml, per one seedling raising box (normally, one seedling raising box is 0.5a at the time of planting). .

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 is used alone or with other active compounds such as insecticides, acaricides, nematicides, fungicides, repellents, synergists and the like. 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 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, when 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 soil or wood surface. (B) Livestock industry, fisheries scene, etc. The pesticidal agent containing the compound of the present invention as an active ingredient is internally or externally parasitic on animals such as pets bred in the livestock industry, fisheries industry and at home. Damage of arthropods, nematodes, flukes, tapeworms, protozoa, etc., which cause direct harm, such as feeding, blood feeding, etc. It is effective in repelling, controlling and controlling, 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; poultry, dogs, cats and the like, and rodents such as 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 order Laminoptera include human fleas such as cat flea and dog flea. Examples of the louse 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 include, for example, the ticks of the ticks, such as the ticks mite, the ticks, the ox tick, the swelling ticks; Dermatophagoids such as Dermatophagoids and Acarina; and Dermatophagoides such as Dermatophagoids and Bovine Dermatophagoides.

Examples of the nematodes of the nematode phylum include the following. Examples of the order Coleoptera include hookworms, pig nematodes, pig lungworms, hairy nematodes, and bovine intestinal nodules. As the roundworms, for example, roundworm, roundworm and the like can be mentioned. As the flatworm phylum,
For example, Schistosoma japonicum, Liver Tetsu, Desertia japonica, Westermani lung fluke, Japanese chicken egg fluke etc. can be mentioned.

Examples of tapeworms include foliate tapeworms, tapeworms, Beneden tapeworms, square tapeworms, striated tapeworms, and tapered 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. For example, Trichomonas and the like can be mentioned.

Further, as the amoeba of the fleshytes, for example, Entamoeba and the like, as the spirozoa subclasses of Piroplasma, for example, Theilaria and Babesia, etc. 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 can be used in combination or as a mixture. Specific examples of the other active compounds include “(A)
Agriculture, forestry scenes, etc. ", but are not limited thereto.

As a specific application method, for example, a compounded pharmaceutical composition which can be mixed with feed of livestock or pets, or which can be orally ingested, such as tablets or pills containing a pharmaceutically acceptable carrier or a coating substance. Orally or as a capsule, paste, gel, beverage, medicated feed, medicinal drinking water, medicated bait, sustained-release large pill, other sustained-release device kept 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 for controlling an arthropod locally or systemically can 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.

For oral administration 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% by weight.
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 compound are usually employed. These forms of use are prepared by homogeneously mixing the active ingredient with a suitably comminuted diluent, filler, disintegrant and / or binder such as starch, lactose, talc, magnesium stearate, vegetable gum, 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 homogeneously dispersed in the feed, a method in which the drug is used as a top dressing, or a method in the form of pellets. In order 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 animals 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,
Generally 0.05 to 50% by weight of the active ingredient compound, preferably 0.1
0.20.2% by weight.

The preparation mixed with a carrier such as an aliphatic alcohol or a hydrocarbon solvent can be directly or topically administered to the external surface of livestock or pets by spraying or direct pouring. Such a formulation generally contains the active ingredient compound in an amount of 0.05 to 50% by weight, preferably 1 to 20% by weight. In this case, it is preferable to add a crystallization inhibitor such as a surfactant or a film-forming agent in order to prevent the precipitation of the active ingredient.

[0079] By incorporating an active ingredient into the base material of pest control devices such as collars and earrings, it can be indirectly administered to livestock and pets. At this time, generally, the amount of the active ingredient compound is about 0.1 to 40% by weight, preferably 1 to 40% by weight.
About 15% by weight. The base material can be appropriately selected according to the use form, and examples thereof include a molded product of a thermoplastic resin such as a vinyl chloride resin and a cloth-like material manufactured from a fiber product such as cotton and polyester. Can be (C) Public health scene, etc. The pest control agent comprising the compound of the present invention as an active ingredient
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 arthropod phylum insects include the following. Examples of the Lepidoptera include ascididae such as Mondriopodidae; Kalehagidae such as Kunugikarehaga; Iragidae such as Aoiraga; And the genus Iridaceae;

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

The Hymenoptera include, for example, hornets, such as wasps; ants, such as giant ants;
As the diptera, for example, mosquitoes such as yamato falcon; smeltaceae such as brassicae; chironomids such as sessile chironomids; Etc .; Drosophilidae such as Sentinia fly; Drosophilidae such as Drosophila melanogaster;
Cheese fly and the like 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. The cockroaches include, for example, German cockroaches such as German cockroaches and Chinese cockroaches; and cockroaches such as Brown cockroaches, Black cockroaches, and Japanese cockroaches.

The Orthoptera includes, for example, the family Corrugidae, such as Madara camphoridae and Camamadia. Examples of the louse include Liceae such as head lice; Liceaceae such as Lice lice. As the Hemiptera, for example, bed bugs such as bed bugs;

The termites include, for example, the termites of the termites such as the termite and the termite; the termites of the termites such as 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 acne;
Examples of the mites include the mites of the tsutsugamushi beetle, etc .;

The true spiders include, for example, the spiders such as Birch spiders; the spiders such as the red spider; the spiders such as the spider; the spiders such as the blue-spotted spider;
Jumping spiders such as Miss jumping flies 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 Coleoptera include those belonging to the order Cymbiformes such as Tobism and Aouzumida, and examples of the order Cestidae include those belonging to the genus Ephedra such as the geese. Examples of the arthropod phylum, Ophiaceae include, for example, the family Papilionidae, such as Toyake-yasuda. 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, poison baits and the like. 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 arbitrary. For example, when protecting the above-mentioned animal products and plant products, spraying oils, emulsions, wettable powders, powders, etc., and resin evaporants 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.

The method of application is such that, for pests such as arthropods that cause direct harm and arthropods that are disease carriers, for example, oil agents, emulsions, Spraying / injection / irrigation / application of wettable powders, spraying powders, etc., fumigants, heated fogs such as mosquito coils, self-burning type smokers, chemical reaction type fogs, fogging etc.
Examples of the method include a method of treating with a preparation such as a ULV agent. In addition, they can be applied in another form such as granules, tablets or poison bait, or by dripping floating powders, granules, etc. into waterways, wells, reservoirs, water tanks and other running or stationary water. Just fine.

[0092] In addition, for "dokuga" which is also a pest 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 use forms are present as a mixture with other active compounds, as mentioned 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 a house or wooden furniture from damage by termites or beetles, for example, spraying / injecting / irrigating / applying oils, emulsions, wettable powders and sols to and around them. , Powders, granules and the like, and a method of spraying a medicine in a use form. 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 an insecticide, acaricide, nematicide, fungicide, repellent, synergist 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. -10% by weight, and preferably 0.01-50% by weight in emulsions, wettable powders and sols. Specifically, for example, when controlling and controlling termites, beetles, etc., 0.01 to 100 g of the active ingredient compound per 1 m ² may be sprayed around 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 preparations and the like, for example, tablets, pills, capsules, pastes, gels, beverages, medicinal feeds, medicaments, and the like, containing pharmaceutically acceptable carriers and coating materials Oral administration as a drinking water, medicated bait, sustained release large pills, other sustained release devices kept in the gastrointestinal tract, or spray, powder,
It can be administered transdermally as grease, cream, ointment, emulsion, lotion, spot-on, pour-on, shampoo and the like.

[0097] Specific formulation and the like are described in "(B) Livestock Industry,
The formulation can be carried out in the same manner as in the method described in the section of “Fishing industry scene”.

[0098]

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 Production of 1- (2,6-dichloro-4-trifluoromethylphenyl) -4-fluoromethylthio-5- (pyridin-4-ylmethylamino) pyrazole-3-carbonitrile (Compound No. 1) 5-amino- To a mixture of 7.7 g of 1- (2,6-dichloro-4-trifluoromethylphenyl) -4-fluoromethylthiopyrazole-3-carbonitrile, 2.2 g of 4-pyridinecarboxaldehyde and 80 ml of toluene
0.1 g of p-toluenesulfonic acid monohydrate was added, and the mixture was heated under reflux for 10 hours while removing generated water. After cooling to room temperature, 30 ml of ice water was added for extraction. The organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to give crude 1-
(2,6-dichloro-4-trifluoromethylphenyl) -4-fluoromethylthio-5- (pyridine-4-
(Ilmethylideneimino) pyrazole-3-carbonitrile was obtained.

The 1- (2,6-dichloro-4- obtained above)
To a solution of trifluoromethylphenyl) -4-fluoromethylthio-5- (pyridin-4-ylmethylideneimino) pyrazole-3-carbonitrile in 100 ml of methanol was slowly added 0.4 g of sodium borohydride. After stirring at room temperature for 1 hour, ice and ethyl acetate were added and extracted. The organic layer was washed with saturated saline and dried over anhydrous sodium sulfate. The residue was purified by silica gel column chromatography, and the compound (No. 1) shown in Table 1 below was used.
6 g were obtained. 204 ° C. ¹ H NMR (CDCl ₃ ): 4.41 (2H, d), 4.68 (1H, t), 5.39 (1H, s),
5.56 (1H, s), 7.04 (2H, d), 7.67 (2H, s), 8.49 (2H, d) Example 2 1- (2,6-dichloro-4-trifluoromethylphenyl) -4-difluoro Methylthio-5-
(Pyridin-2-ylmethylamino) pyrazole-3-
Production of Carbonitrile (Compound No. 2) 8.0 g of 5-amino-1- (2,6-dichloro-4-trifluoromethylphenyl-4-difluoromethylthiopyrazole-3-carbonitrile, 2-pyridinecarboxaldehyde 2 To a mixture of 0.2 g and 60 ml of toluene
20 mg of p-toluenesulfonic acid monohydrate was added, and the mixture was refluxed for 3 hours while removing generated water. After cooling to room temperature, 0.1 ml of triethylamine and 30 ml of ice water were added for extraction. The organic layer was dried over anhydrous sodium sulfate.
The solvent was distilled off under reduced pressure to obtain crude 1- (2,6-dichloro-4-trifluoromethylphenyl) -4-difluoromethylthio-5- (pyridin-2-ylmethylideneimino) pyrazole-3-carbonitrile. Was.

The 1- (2,6-dichloro-4- obtained above)
0.7 g of sodium borohydride was gradually added to a 50 ml solution of trifluoromethylphenyl) -4-difluoromethylthio-5- (pyridin-2-ylmethylideneimino) pyrazole-3-carbonitrile in methanol.
After stirring at room temperature for 1 hour, ice and ethyl acetate were added and extracted. The organic layer was washed with saturated saline and dried over anhydrous sodium sulfate. The residue was purified by silica gel column chromatography, and the compound (No. 2) 8.4 shown in Table 1 below was used.
g was obtained. Melting point 117-120 ° C ¹ H NMR (CDCl ₃ ): 4.57 (2H, d), 5.88 (1H, m), 6.73 (1H, t),
7.19 (2H, t), 7.66 (1H, t), 7.77 (2H, s), 8.41 (1H, d) Example 3 The compounds described in Table 1 were synthesized according to the methods of Examples 1 and 2. Hereinafter, Compound No. And ¹ H NMR data. N0.3 ¹ H NMR (CDCl ₃ ): 4.47 (2H, d), 4.67 (1H, bs), 6.69 (1H,
t), 7.05 (2H, d ), 7.68 (2H, s), 8.51 (2H, d) N0.4 1 H NMR (CDCl 3): 3.25 (2H, q), 4.44 (2H, d), 4.67 ( 1H, t),
7.04 (2H, d), 7.64 (2H, s), 8.48 (2H, d)

[0101]

[Table 1]

Production Example 1 1- (2,6-dichloro-4-)
Trifluoromethylphenyl) -5- (pyridine-2-
Production of ylmethylamino) pyrazole-3-carbonitrile (1) In a three-neck flask, 40 ml of dehydrated toluene, 1-
(2,6-dichloro-4-trifluoromethylphenyl) -5-aminopyrazole-3-carbonitrile 10
g (31.1 mmol), 4.55 g of 2-pyridinecarboxaldehyde and 0.0 of p-toluenesulfonic acid.
3 g were charged and refluxed for 3 hours under nitrogen. After washing the reaction solution three times with water and drying the organic phase with magnesium sulfate, magnesium sulfate is removed by filtration and the solvent is distilled off to obtain 1- (2,6-dichloro-4-trifluoromethylphenyl). -5- (Pyridin-2-ylmethylideneimino) pyrazole-3-carbonitrile 1
2.63 g of solid (purity 98.6 LC%, 30.3 mm
ol, yield 97.3%).

(2) Dehydrated methanol 2 was placed in a three-necked flask.
000 ml, 1- (2,6-dichloro-4-trifluoromethylphenyl) -5- (pyridin-2-ylmethylideneimino) pyrazole-3-carbonitrile 47.7
g (purity 96%, 109.9 mmol) and 2.0 g of sodium tetrahydroborate were charged and reacted under nitrogen for 2 hours. Thereafter, the crystals formed in the reaction solution were collected by filtration, washed with water and methanol, and then dried in vacuo.
42.84 g of (2,6-dichloro-4-trifluoromethylphenyl) -5- (pyridin-2-ylmethylamino) pyrazole-3-carbonitrile (purity 9
7.5%, 101.3 mmol, yield 84.1%).

Production Example 2 Bis [1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-5
-(Pyridin-2-ylmethylamino) pyrazole-4
-Yl)] Disulfide (raw material of Example 4) In a test tube, 1 ml of acetic acid, 3 ml of dehydrated toluene, Production Example 1
Of 1- (2,6-dichloro-4-trifluoromethylphenyl) -5- (pyridin-2-ylmethylamino) pyrazole-3-carbonitrile obtained by the method of 1.
g (0.485 mmol), sulfur monochloride (S ₂ Cl ₂ ) 4
0 mg was charged and reacted under nitrogen for 3 hours. Thereafter, the crystals formed in the reaction solution are collected by filtration, and an aqueous solution of sodium bicarbonate,
After neutralization and extraction with ethyl acetate, liquid separation was performed, the organic phase was dried over magnesium sulfate, magnesium sulfate was filtered, ethyl acetate was distilled off, and bis [1- (2,6-
Dichloro-4-trifluoromethylphenyl) -3-cyano-5- (pyridin-2-ylmethylamino) pyrazol-4-yl)] disulfide 200 mg (purity = 8)
(5.6%, 0.193 mmol, yield = 79.7%).

Example 4 Compound No. using chlorodifluoromethane Preparation of 2 Bis [1- obtained by the method of Preparation Example 2 under a nitrogen atmosphere
(2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-5- (pyridin-2-ylmethylamino) pyrazol-4-yl)] disulfide 500 m
g (0.565 mmol) and absolute ethanol (15
mL) was charged into a 50 mL three-neck flask and cooled to 3 ° C. While stirring, sodium borohydride (64 m
g, 3.0 eq. ) Was added slowly. It returned to room temperature and stirred for 1 hour. Subsequently, while blowing chlorodifluoromethane into the reaction solution using a gas introduction tube, sodium ethoxide (192 m 2) dissolved in 5 ml of absolute ethanol was used.
g, 2.83 mmol, 5.0 eq. ) Was slowly dropped into the reaction solution. After the completion of the reaction, ethanol was distilled off, 20 mL of distilled water was added, and ethyl acetate (75 mL ×
Extracted in 2). The combined ethyl acetate extracts were washed with distilled water (30 mL) and dried over anhydrous magnesium sulfate. After filtration of the magnesium sulfate, the ethyl acetate was distilled off and the desired product, 1- (2,6-dichloro-4-trifluoromethylphenyl) -4-difluoromethylthio-5- (pyridin-2-ylmethylamino) was obtained. ) Pyrazole-3-carbonitrile was obtained in 64% yield.

Example 5 Compound No. using difluoromethylsulfenyl chloride Production of 2 In a nitrogen atmosphere, 1- (2, obtained by the method of Production Example 1
6-dichloro-4-trifluoromethylphenyl) -5
-(Pyridin-2-ylmethylamino) pyrazole-3
500 mg (1.21 mmol) of carbonitrile are suspended in 5.0 ml of anhydrous dichloromethane and, while stirring, 180 mg of difluoromethylsulphenyl chloride
2.0 mL of anhydrous dichloromethane containing (1.52 mmol, 1.25 eq.) Was added dropwise at room temperature and reacted for 2 hours. 100 mL of ethyl acetate was added, and the organic layer was washed with 20 mL of a saturated aqueous solution of sodium hydrogen carbonate, followed by 20 mL of water, and dried over anhydrous magnesium sulfate. After filtering off magnesium sulfate, the solvent was distilled off under reduced pressure, and the crude product was recrystallized with a mixed solvent of hexane / ethyl acetate (3/1) to give 535 mg of 1- (2,6-dichloro- 4
-Trifluoromethylphenyl) -4-difluoromethylthio-5- (pyridin-2-ylmethylamino) pyrazole-3-carbonitrile was obtained (yield 90%, purity 96%).

Hereinafter, examples of preparations 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. <Formulation Example 1> Wetting agent 20 parts by weight of the compound of the present invention, 20 parts by weight of Carplex # 80 (white carbon, Shionogi & Co., Ltd., trade name), ST kaolin clay (kaolinite, Tsuchiya Kaolin 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.), The mixture was uniformly mixed and pulverized to obtain a wettable powder containing 20% by weight of the active ingredient.

<Formulation Example 2> Dust 2 parts by weight of the compound of the present invention, clay (manufactured by Nippon Talc) 9
3 parts by weight, carplex # 80 (white carbon,
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 were 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, Toho Chemical Co., trade name) 15 parts by weight, add 20% by weight of active ingredient
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, mixed well and pulverized to obtain an active ingredient 20.
By weight, a flowable agent was obtained.

<Formulation Example 5> Granules 2 parts of the compound of the present invention, 40 parts of bentonite, clay 53
And 5 parts of calcium ligninsulfonate were uniformly pulverized and mixed, water was added and kneaded well, followed by extrusion granulation and drying and sizing to obtain granules. <Formulation Example 6> Granules After mixing silica sand in a tumbling granulator and making it wet, 2 parts of the compound of the present invention, 3 parts of calcium ligninsulfonate, and 3 parts of polyvinyl alcohol (PVA), which were previously pulverized and mixed, were added. 5
Parts, 0.5 parts of white carbon and 94 parts of silica sand, coated, dried and sized to obtain granules.

<Formulation Example 7> Granule seed coating powder 2 parts of the compound of the present invention, calcium ligninsulfonate 6
Parts, polyvinyl al, and 82 parts of clay were uniformly mixed and pulverized, and a powder prepared and mixed with a pre-moistened seed were air-dried to obtain a coated seed. Hereinafter, a test example of an agricultural and horticultural insecticide containing the compound of the present invention as an active ingredient,
The mode of use of the present invention is not limited to the following.

<Test Example 1> Insecticidal effect of brown planthopper on larvae Rice germination seedlings were set on a glass cylinder (inner diameter 3 cm x length 17 cm), and five fourth-stage larvae of brown planthopper were released. 0.5 ml of a water dilution of the agricultural and horticultural insecticide of the present invention produced according to the formulation of Formulation Example 3 was sprayed on the above-mentioned glass cylinder using a spray tower (manufactured by Mizuho Rika) (1 concentration, 2 repetitions). The larvae were kept in a constant temperature room at 25 ° C., and after 5 days from the treatment, the larvae were examined for viability and writhing, and the killing rate (%) was determined by assuming that the writhing larva was 頭 dead. The results are shown in Table 2 (the compound numbers in the table correspond to Table 1).

[0113]

[Table 2]

<Test Example 2> Insecticidal effect on Japanese larva of Japanese moth Cabbage cut leaves (6 cm in diameter) were immersed in a water dilution of the agricultural and horticultural insecticide of the present invention produced according to the formulation of Preparation Example 1 for 1 minute. After immersion, air-dry the plastic cup (7
cm) and five third-instar larvae of the Japanese moth were released into the cup (one concentration, two 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, and the killing rate (%) was determined by assuming that the agony insects were 頭 dead. Table 3 shows the results
(In the table below, the compound numbers correspond to Table 1).

[0115]

[Table 3]

Test Example 3 Insecticidal Effect of Azuki Bean Weevil on Adult Insect Bean 2 in a glass cylinder (inner diameter 3 cm × length 15 cm)
Individually, 10 adults of Azuki weevil were released. 0.3 ml of a water dilution of the agricultural and horticultural insecticide of the present invention produced according to the formulation of Formulation Example 3 was sprayed onto the above-mentioned glass cylinder using a spray tower (manufactured by Mizuho Rika) (one concentration, 2 repetitions). 25 ° C
4 days after the treatment, the larvae were examined for life and death and agony, and the killing rate (%) was determined by assuming that the agony worms were １ ／ dead. The results are shown in Table 4 (the compound numbers in the table correspond to Table 1).

[0117]

[Table 4]

<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) filled with water, and 5 to 6 peach peach aphids were inoculated per leaf. . After inoculation, glass cylinder (diameter: 3.5c
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 ( 1 concentration, 2 replicates). 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. The results are shown in Table 5 (the compound numbers in the table correspond to Table 1).

[0119]

[Table 5]

<Test Example 5> Insecticidal effect of rice planthopper on larvae of brown planthopper through osmotic transferability The roots of rice seedlings (plant height: about 10 cm) planted in plastic cups were washed with water, and the soil was thoroughly washed off without damaging the fine roots. . Urethane chips with cuts (diameter 3cm,
(2 cm in height), and insert the root into an Erlenmeyer flask containing 50 ml of a medicinal solution (water dilution of the agricultural and horticultural insecticide of the present invention manufactured according to the formulation of Formulation Example 1). ~ 3 tubes / flask), and a urethane chip was inserted between the mouths of the flask to fix the rice seedlings. A glass tube (diameter 3 cm, height 5 cm) was placed thereon, sandwiched between urethane chips, and fixed with tape. In this state, it was kept in a constant temperature room at 25 ° C. for 3 days. After placing five brown planthopper larvae in this glass tube, cover with a urethane chip,
Was kept in a constant temperature room. (1 concentration, 2 replicates). After processing 4
On the day, larvae were examined for life and death and agony, and
The insect kill rate (%) was determined as the head. This test was performed for two chemical solutions having different active ingredient concentrations. The results are shown in Table 6 (the compound numbers in the table correspond to Table 1).

As a control compound, JP-A-10-33
Compounds I, II and III described in JP 8676 were similarly subjected to the test.

[0122]

Embedded image

[0123]

[Table 6]

Brown planthopper is an important problem pest species in agricultural and horticultural scenes, but its application method such as spraying on foliage is not effective enough when discovery is delayed or when the drug is not sufficiently distributed to the root. There may not be. This species has the characteristic of inhabiting the roots of rice etc. and damaging it by sucking. Therefore, a more efficient control method is to treat the surface of the soil with a drug (granule treatment) before the occurrence of many species Is mentioned. However, in order to achieve a high control effect by such a method, it is necessary to have a property of penetrating into a plant as a property of the drug. As is evident from Table 6, the compound of the present invention and Compound I both showed insecticidal activity through high systemic transfer to this species, which is an important problem pest. On the other hand, Compounds II and III had such a low effect, and were therefore clearly less effective than the compounds of the present invention.

<Test Example 6> In Vitro Cellular Metabolic Cooperation Inhibition Test (IMC) In this test example, the presence or absence of carcinogenicity (cancer promoting activity) of a compound was determined by using the inhibitory effect of intercellular communication via gap junction as an index. It was considered. In this test, 6-thioguanine (6
-TG) and the following compounds were added and treated. If intercellular communication is normal, toxic metabolites of 6-TG generated in hgprt + cells (6-TG sensitive) also transfer to hgprt- cells (6-TG resistant) via gap junctions. Both cells die. On the other hand, when intercellular communication is inhibited by the test compound, hgprt
-Only cells survive and form colonies.

The compound of the present invention no. 2 and Test Example 5 above
As a result of conducting a test on Comparative Compound I, which exhibited high systemic migration activity, Compound No. 2 was negative, but compound I was positive at 7.5 and 15 μg / ml with a significant increase in colony formation. Therefore,
From this test result, it was found that the compound of the present invention had a lower carcinogenic risk than Compound I.

<Test Example 7> Insecticidal Effect on Cat Flea A chemical solution diluted to a predetermined concentration in a circular filter paper (diameter: 10 cm) was added.
After dropping 7ml and drying, cylinder (diameter: 10cmx height 30cm)
Laid on the bottom. 10 fleas were released in it and 1 after treatment
The number of deaths on day 2 and day 2 was investigated, and the mortality was calculated based on the results. The results are shown in Table 7 (the compound numbers in the table correspond to Table 1).

[0128]

[Table 7]

[0129]

The 1-aryl-3-cyano-5 of the present invention
The pyridylalkylaminopyrazole derivative is a compound useful as a novel pesticide, which is excellent in insecticidal effect, has a broad insecticidal spectrum, has a systemic activity, and is highly safe.

 ──────────────────────────────────────────────────続 き Continued on the front page (72) Inventor Toshiki Fukuchi 1000 Kamoshita-cho, Aoba-ku, Yokohama-shi, Kanagawa Prefecture Inside Mitsubishi Chemical Corporation (72) Inventor Kazuya Okano 8-3-1 Chuo, Ami-cho, Inashiki-gun, Ibaraki Mitsubishi Inside Chemical Co., Ltd. (72) Inventor Yoshitomo What, 3-3-1 Chuo, Ami-cho, Inashiki-gun, Ibaraki Prefecture Inside Mitsubishi Chemical Co., Ltd. (72) Akiko Miyauchi 8-3-1 Chuo, Ami-cho, Inashiki-gun, Ibaraki Mitsubishi F term in Chemical Co., Ltd. (reference) 4C063 AA01 BB09 CC22 DD11 EE03 4H011 AC01 AC04 BA01 BB09 BC03 BC06 BC07 BC18 BC19 BC20 DA02 DA14 DA15 DA16 DC04 DH03 DH14

Claims (12)

[Claims] 1. A 1-aryl-3-cyano-5-pyridylalkylaminopyrazole derivative represented by the following general formula (1). Embedded image (In the above formula, X represents an N or C-halogen atom;
¹ represents a haloalkyl group (excluding a perhaloalkyl group), R ² represents a hydrogen atom or an alkyl group,
R ³ represents a hydrogen atom, an alkyl group or an acyl group, R ⁴
Represents a hydrogen atom, a hydroxyl group, an alkyl group, a haloalkyl group, an alkoxy group, a haloalkoxy group, an alkylthio group, an alkylsulfinyl group, an alkylsulfonyl group, a halogen atom, a nitro group or a cyano group. ) 2. The 1-aryl-3-cyano-5-pyridylalkylaminopyrazole derivative according to claim 1, wherein R ⁴ is a hydrogen atom. 3. The 1-aryl-3-cyano-5 according to claim 1, wherein R ¹ is a haloalkyl group having 1 to 4 carbon atoms (excluding a perhaloalkyl group). Pyridylalkylaminopyrazole derivatives. 4. The 1-aryl-3-cyano-5-pyridylalkylaminopyrazole derivative according to claim 1, wherein R ² and R ³ are hydrogen atoms. 5. A pest control agent comprising the 1-aryl-3-cyano-5-pyridylalkylaminopyrazole derivative according to any one of claims 1 to 4 as an active ingredient. 6. An insecticide comprising the 1-aryl-3-cyano-5-pyridylalkylaminopyrazole derivative according to claim 1 as an active ingredient. 7. An agricultural and horticultural insecticide comprising the 1-aryl-3-cyano-5-pyridylalkylaminopyrazole derivative according to claim 1 as an active ingredient. 8. An insecticide for pets, comprising the 1-aryl-3-cyano-5-pyridylalkylaminopyrazole derivative according to claim 1 as an active ingredient. 9. A pyrazole represented by the following general formula (2)
Derivatives with R¹SX¹(R ¹Is synonymous with general formula (1),
X¹Represents a chlorine atom, bromine atom, alkylsulfonyl group, etc.
Or an arylsulfonyl group).
The 1-ary according to any one of claims 1 to 4, wherein
Ru-3-cyano-5-pyridylalkylaminopyrazo
A method for producing a derivative. Embedded image(In the above formula, X represents an N or C-halogen atom;
^TwoRepresents a hydrogen atom or an alkyl group;^ThreeIs a hydrogen atom,
An alkyl group or an acyl group;^FourIs hydrogen atom, water
Acid group, alkyl group, haloalkyl group, alkoxy group,
Alkoxy, alkylthio, alkylsulfini
Group, alkylsulfonyl group, halogen atom, nitro group
Or a cyano group. ) 10. The 1-aryl-3 according to claim 1, wherein a haloalkylating agent is allowed to act on a pyrazole derivative represented by the following general formula (3).
A method for producing a cyano-5-pyridylalkylaminopyrazole derivative. Embedded image (In the above formula, X represents an N or C-halogen atom;
² represents a hydrogen atom or an alkyl group; R ³ represents a hydrogen atom;
R ⁴ represents a hydrogen atom, a hydroxyl group, an alkyl group, a haloalkyl group, an alkoxy group, a haloalkoxy group, an alkylthio group, an alkylsulfinyl group, an alkylsulfonyl group, a halogen atom, a nitro group or a cyano group; . ) 11. The 1-aryl-3 according to claim 1, wherein a haloalkylating agent is allowed to act on a pyrazole derivative represented by the following general formula (4).
A method for producing a cyano-5-pyridylalkylaminopyrazole derivative. Embedded image (In the above formula, X represents an N or C-halogen atom;
² represents a hydrogen atom or an alkyl group; R ³ represents a hydrogen atom;
R ⁴ represents a hydrogen atom, a hydroxyl group, an alkyl group, a haloalkyl group, an alkoxy group, a haloalkoxy group, an alkylthio group, an alkylsulfinyl group, an alkylsulfonyl group, a halogen atom, a nitro group or a cyano group; . ) 12. The 1-aryl-3 according to claim 1, wherein a haloalkylating agent is allowed to act on a pyrazole derivative represented by the following general formula (5).
A method for producing a cyano-5-pyridylalkylaminopyrazole derivative. Embedded image (In the above formula, X represents an N or C-halogen atom;
² represents a hydrogen atom or an alkyl group; R ³ represents a hydrogen atom;
R ⁴ represents a hydrogen atom, a hydroxyl group, an alkyl group, a haloalkyl group, an alkoxy group, a haloalkoxy group, an alkylthio group, an alkylsulfinyl group, an alkylsulfonyl group, a halogen atom, a nitro group or a cyano group; . )