TW201127291A - Diaryltriazole derivative or its salt; insecticide, miticide, nematicide or soil pesticide containing it; and process for its production - Google Patents

Abstract

To provide a novel insecticide, miticide, nematicide or soil pesticide. The present invention provides an insecticide, miticide, nematicide or soil pesticide containing a diaryltriazole derivative of the formula (I) or its salt, as an active ingredient: wherein R1 is alkyl which may be substituted by halogen, alkenyl which may be substituted by halogen, or alkynyl which may be substituted by halogen, R2 is phenyl which may be substituted by X, or pyridyl which may be substituted by X; X is halogen, alkyl, haloalkyl, alkenyl, alkynyl, alkoxy, haloalkoxy, alkylthio, amino, nitro or cyano; each of R3 and R4 which are independent of each other, is a hydrogen atom, halogen, alkyl, alkenyl, alkynyl or cyano; R5 is alkyl which may be substituted by A, alkenyl which may be substituted by A, or alkynyl which may be substituted by A; A is halogen, cyano or cycloalkyl; and n is 0, 1 or 2.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an insecticide, an acaricide, a nematicide or a soil pesticide containing a novel diaryltriazole derivative or a salt thereof as an active ingredient. [Prior Art] Patent Document 1 discloses a phenyltriazole derivative which can be used as an insecticide or an acaricide, however, this document differs from the present invention in a substituent corresponding to R2 in the formula (I) mentioned below. Compound. Further, Patent Document 2 discloses a (3-sulfo-substituted phenyl)heteroaryl derivative which can be used as an insecticide or an acaricide. However, the phenyl group substituted on the triazole ring is different from this. Inventive compound. Patent Document 1: W099/55668 Patent Document 2: JP-A-2008-308448 SUMMARY OF THE INVENTION The object of the present invention has been to use many insecticides, acaricides, nematicides or soil pesticides for many years, but Many of them have various problems, and the lack of efficacy is limited by the use of pests and the like to obtain resistance. Therefore, it is desirable to develop novel insecticides, acaricides, nematicides or soil pesticides that are substantially free of such problems. Method for achieving the purpose-5-201127291 The present inventors have performed various cockroaches on phenyltriazole derivatives to find an excellent insecticide, acaricide, nematicide or soil result, and have found novel diaryl groups. The triazole derivatives are extremely high, and the present invention has been completed in safety against crops, natural enemies of insects, etc., or mammals, particularly at low doses for extremely high control of the two-spotted spider mites. Namely, the present invention relates to a diaryl group represented by the formula (I) or a salt thereof: Control effect, same, and thus azole derivatives

Wherein R 1 is an alkyl group which may be substituted by halogen, an alkynyl group which may be substituted by a halogen group or may be halogen; and R 2 is a pyridyl group which may be X-substituted or X-substituted; X is a halogen, an alkyl group, Halogen, alkynyl, alkoxy, haloalkoxy, alkylthio, amine or cyano; each R3 and R4 are independent of each other and are a hydrogen atom & base 'alkenyl, alkynyl or cyanide R5 is an alkenyl group which may be substituted by A substituted alkane A or an alkynyl group which may be substituted by A; A is a halogen ring-based group: and η is 0, 1, or 2. Further, the present invention relates to a phenyl group, an alkyl group, a nitro group, a halogen group, a pharmaceutically acceptable group, a cyano group or a aryl group of a olefin having a (1) bisaryltriazole derivative or a salt thereof as an active ingredient. Containing insecticide 201127291, acaricide, nematicide or soil pesticide, a method of controlling insects, pots, nematodes or soil pests by applying such compounds and a method of manufacture. Advantageous Effects of Invention The insecticide, the lethal agent, the nematicide or the soil pesticide containing the diaryltriazole derivative of the above formula (I) or a salt thereof as an active ingredient has extremely high resistance against insects and cockroaches at low doses. , the control effect of nematodes or soil pests. BEST MODE FOR CARRYING OUT THE INVENTION As the halogen in the formula (I) or the halogen as a substituent, an atom of fluorine, chlorine, bromine or iodine may be mentioned. The number of halogens as a substituent may be 1 or more, and if it is more than 1, the individual halogens may be the same or different. Further, the substitution position of the halogens may be any position. The alkyl group in the formula (I) may be a straight chain or a branched chain. As a specific example, mention may be made of Ci-6, such as methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl or hexyl. As the cycloalkyl group in the formula (I), for example, a c3-6 cycloalkyl group such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group or a cyclohexyl group can be mentioned. The alkenyl group in the formula (I) may be a straight chain or a branched chain. As a specific example thereof, a c2-6 alkenyl group such as a vinyl group, a 1-propenyl group, an allyl group, an isopropenyl group, a 1-butenyl group, a 1,3-butadienyl group or a 1-hexenyl group can be mentioned. The alkynyl group in the formula (I) may be a straight chain or a branched chain. As a specific example thereof, a c2.6 alkynyl group such as an ethynyl group, a 2-butynyl group, a 2-pentynyl group, a 3-methyl-1-butynyl group, a 2-penten-4-ynyl group may be mentioned. Or 3-hexynyl. The pyridyl group represented by R2 in the formula (1) may be, for example, a 2-pyridyl group, a 3-pyridyl group or a 4-pyridyl group. Among them, 2 _pyridyl is preferred. Further, when the pyridyl substituent X is substituted, the plural oximes may be the same or different, and the number of substituents is 1 to 4. When the phenyl group represented by R2 in the formula (I) is substituted with the substituent X, the plural X may be the same or different from the number of substituents of 1 to 5. The salts of the diaryltriazole derivatives of the formula (I) include all types as long as they are acceptable in the art. For example, mention may be made of ammonium salts such as -methyl saddle or triethylammonium salts; mineral acid salts such as hydrochlorides, perchlorates, sulfates or nitrates; or organic acid salts such as acetates or Methanesulfonate. The above diaryltriazole derivatives of the formula (I) may have isomers such as optical isomers or geometric isomers, and the isomers and mixtures thereof are both included in the present invention. In this specification, isomers are in the form of a mixture unless otherwise stated. Further, in the present invention, various isomers other than the foregoing may be included in the scope of common knowledge in the technical field. Further, depending on the type of isomer, it may have a chemical structure different from that of the above formula (I), but it is sufficient for those skilled in the art to confirm that it is in a heterogeneous relationship and fall within the scope of the present invention. The diaryltriazole derivative of the above formula (I) or a salt thereof (hereinafter referred to as a compound of the present invention) can be produced by the following methods Π] to [6] and according to a general salt production method. However, the invention is in no way limited to such methods. 201127291 Method [1]

(Π) (TV) (I) In the above formula, R1, R2, R3, R4, R5 and n are as defined above. Process [1] is a process for producing a compound of formula (I) which comprises reacting a compound of formula (II) with a compound of formula (III) to give a compound of formula (IV), which is subjected to a dehydrogenation reaction, And the method [1] comprises the aforementioned steps 1-1 and 1-2. The individual reaction steps are described in detail below. The reaction in Process 1-1 can usually be carried out in the presence of an acid and a solvent. As the acid, one or more kinds selected from the group consisting of, for example, acetic acid, hydrochloric acid, sulfuric acid, methanesulfonic acid and p-toluenesulfonic acid. The acid amount may be 0.05 to 2 moles, more preferably 0.1 to 1 moles, relative to the compound of the formula (II). The solvent is not particularly limited as long as the reaction can be carried out, and may be one or more suitable selected from, for example, ethers such as diethyl ether, butyl methyl ether, tetrahydrofuran, dioxane and dimethoxyethane; halogenated hydrocarbons such as Chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane, trichloroethane and dichloroethylene; aromatic hydrocarbons such as benzene, toluene and xylene; and aliphatic hydrocarbons Such as pentane, hexane, heptane, octane and cyclohexane. The reaction in the step 1-1 can be carried out usually at 20 to 250 ° C, preferably at 2 to 150 ° C, and the reaction time is usually about 0.5 to 24 hours, preferably about 1 to 20 hours. . After the completion of the reaction of the step 1-1, the reaction of the step 1-2 can be carried out continuously after the isolation of the obtained formula (IV) -9-201127291 or without isolation. When the compound of formula (IV) is isolated, the reaction of steps 1-2 is usually carried out in the presence of a base or an oxidizing agent. When the compound of the formula (IV) is not isolated, depending on the type of the compound of the formula (III) to be used, the reaction can be carried out even without using a base or an oxidizing agent. As the base, one or more suitable ones selected from, for example, amines such as trimethylamine, triethylamine, triisopropylamine, diisopropylamine, pyridine, 2-methylpyridine, 3-methyl can be selected. Pyridine, 4-methylpyridine, 4-dimethylaminopyridine, 2,6-lutidine, 4-pyrrolidinopyridine, N-methylmorpholine, N,N-dimethylaniline, N,N-diethylaniline, N-ethyl-N-methylaniline, 1,8-diazabicyclo[5.4.0]-7-undecene and 1,4-diazabicyclo[ 2.2.2] Octane. The base may be used in an amount of 0.1 to 5 moles, preferably 1 to 3 moles, relative to the compound of the formula (IV). As the oxidizing agent, one or more suitable ones selected from, for example, 2,3-dichloro-5,6-dicyano-I,4-benzoquinone, tetrachlorophenylhydrazine, o-tetrachlorophenylhydrazine, hydrogen peroxide , ammonium peroxodisulfate, sodium peroxodisulfate, potassium peroxodisulfate, potassium permanganate, OXONE (trademark, manufactured by EI DuPont; potassium peroxodisulfate), sodium hypochlorite, sodium chlorite, benzoyl peroxide Formamidine, tert-butyl hydroperoxide, oxygen, and the like. The oxidizing agent can be used in an amount of from 1 to 10 moles, preferably from 1 to 4 moles, relative to the compound of formula (IV). The reaction in the step 1-2 is usually carried out in the presence of a solvent. The solvent is not particularly limited as long as it can be used for the reaction, and the same as the aforementioned step 1-1 can be used. Further, in addition to the above, one or more suitable ones may be selected, for example, from a polar aprotic solvent such as acetonitrile, propionitrile, N,N-dimethylformamide, N,N-dimethylacetamidine. Amine, dimethyl hydrazine, trimethyl hexamethyl phosphate-10-201127291 Amine, cyclobutyl hydrazine and N-methyl-2-pyrrolidone; alcohols such as methanol, ethanol, n-propanol, isopropanol , n-butanol and tert-butanol; organic acids such as acetic acid and propionic acid; water; and esters such as methyl acetate and ethyl acetate. The reaction in the step 1-2 can be usually from -20 to 250. (: proceeding, preferably at 〇 to 150 ° C, and the reaction time is usually about 0.5 to 48 hours, preferably about 1 to 30 hours.) [2]

[2] H^NrRl ηΝ·^Ν R2C0C1(V) r3A —1 T^S(0)nR5 R4 (Π) In the above formula, R1, R2, R3, R4, R5 and n are as defined above. The method [2] is a method for producing a compound of the formula (I), which comprises reacting a compound of the formula (π) with a compound of the formula (V), and will be described in detail. The reaction of the method [2] can be usually carried out in the presence of a base and a solvent. As the test, the same as step I-2 of the method [1] can be used. The base may be used in an amount of from 0.5 to 5 moles per mole of the compound of the formula (Π), preferably from 1 to 2 moles of the solvent. The solvent is not particularly limited 'as long as it can be used for the reaction, and can be used and used [ 1] The same is illustrated in steps 1-1. The reaction of the method [2] can be carried out usually at -20 to 25 Torr, preferably at 〇 to 150 ° C, and the reaction time is usually about 0.5 to 48 hours, preferably about 3 to 12 hours. 201127291 R1 method [3]

R4 (I-a) oxidation R1

S(〇)nbR5 R4 (I-b) In the above formula, R1, R2, R3, R4 and R5 are as defined above, and nb is 1 or 2. The method [3] is a method for producing a compound of the formula (I-b), which comprises oxidizing a compound of the formula (I-a), and the oxidation reaction of the method [3] can be carried out in the presence of an oxidizing agent. The oxidizing agent' may be one or more suitable selected from, for example, meta-chloroperbenzoic acid, hydrogen peroxide, sodium periodate, OXONE (trademark, manufactured by Pont·Ι. DuPont; potassium hydrogen peroxysulfate), hypochlorous Tert-butyl acid and sodium hypochlorite. Among these oxides, m-chloroperbenzoic acid and/or hydrogen peroxide are preferred, and m-chloroperbenzoic acid is more preferred. The oxidizing agent may be used in an amount of from 1 to 1 moles per mole of the compound of the formula (I-a), preferably from 1 to 6 moles. The reaction of the method [3] can usually be carried out in the presence of a solvent. The solvent is not particularly limited as long as it can be used for the reaction, and may be one or more suitable ones selected from, for example, ethers such as diethyl ether, butyl methyl ether, tetrahydrofuran, dioxane, and dimethoxyethane; halogenated hydrocarbons, Such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane, trichloroethane and dichloroethylene; aromatic hydrocarbons such as benzene, toluene and xylene; aliphatic hydrocarbons , such as pentane, hexane, heptane, octane and cyclohexane; polar aprotic solvents such as acetonitrile, propionitrile, N,N-dimethylformamide 'N,N-dimethylacetamide, Dimethyl sulfoxide, trimethylamine hexamethylphosphate, cyclobutyl sulphate and N-methyl-2-pyridinone-12- 201127291 : alcohols such as methanol, ethanol, n-propanol, isopropanol, N-butanol and second butanol; organic acids such as acetic acid and propionic acid; water; and ketones such as acetone, methyl ethyl ketone and cyclohexanone. The reaction of the method [3] can be carried out in a reaction system at a temperature of from -30 ° C to reflux temperature, preferably -1 CTC to loot: and the reaction time is usually about 11 to 48 hours. .5 to 24 hours. Method [4]

R4 (Ic) R4 (Id) In the above formula, R1, R2, R3, R4 and η are as defined above, an alkyl group which may be substituted with A 1 , an alkenyl group which may be substituted with a 1 , or may be subjected to A a substituted alkynyl group; the ft. 5 £1 is a haloalkyl group which may be substituted by A2, an alkenyl group which may be substituted by A2, or a haloalky group which may be substituted by A2; A1 is a halogen, a cyano group or a cycloalkane And A2 is a cyano group or a cycloalkyl group. The method [4] is a method for producing a compound of the formula (i-d) which comprises halogenating a compound of the formula (I-c) and will be described in detail. The halogenation reaction of the method [4] can be carried out in the presence of a halogenating agent. As the gerifier, one or more suitable ones selected from, for example, chlorine, bromine, chloramine, N-chloropyrmine, N-bromosinium imide, phosphorus pentachloride, phosphonium chloride, phosphonium Bromine, sulfinium chloride and sulfinium bromide. The halogenation reaction of the method [4] can be usually carried out in the presence of a solvent. Solvent No-13 - 201127291 is particularly limited as long as it can be used for the reaction, and may be one or more suitable selected from, for example, ethers such as diethyl ether, butyl methyl ether, tetrahydrofuran, dioxane and dimethoxyethane; Halogenated hydrocarbons such as chlorobenzene 'dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane, trichloroethane and dichloroethylene; aliphatic hydrocarbons such as pentane, hexane, gly Alkyl octane and cyclohexane; polar aprotic solvents such as acetonitrile, propionitrile, hydrazine, hydrazine-dimethylformamide, hydrazine, hydrazine-dimethylacetamide, dimethyl hydrazine, hexamethyl Triammonium phosphate, cyclobutyl hydrazine and hydrazine-methyl-2-pyrrolidone; organic acids such as acetic acid and propionic acid: water; and esters such as methyl acetate and ethyl acetate. The halogenation reaction of the method [4] can be carried out usually at -100 to 150 ° C, preferably at -10 to 110 ° C, and the reaction time is usually about 0.1 to 48 hours, preferably about 0.5 to 24 hours. Method [5]

R4 (VI) R4 J 2 (XIV) R4 σ-a) In the above formula, R1, R2, R3, R4 and R5 are as defined above, and L1 is a leaving group. The method [5] is a method for producing a compound of the formula (I-a), which comprises a reaction of a compound of the formula (VI) or (XIV) with a compound of the formula (VII), and will be described in detail. The reaction of the method [5] can be usually carried out in the presence of a base and/or a reaction initiator. The base may be any base as long as it exhibits a pH of at least 8, and may be -14-201127291 or a plurality of suitable ones selected from, for example, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkaline earth metal hydroxides , such as calcium hydroxide and magnesium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; alkali metal hydrogencarbonates such as sodium hydrogencarbonate and potassium hydrogencarbonate; alkali metal hydrides such as sodium hydride and potassium hydride; Metal alkoxides such as sodium methoxide, sodium ethoxide and potassium butoxide; and organometallics such as methyllithium, butyllithium, methylmagnesium bromide and lithium diisopropylamide. Among these bases, alkali metal carbonates, alkali metal hydrogencarbonates, alkali metal hydrides and alkali metal alkoxides are preferred, and sodium carbonate, sodium hydrogencarbonate, potassium carbonate, potassium hydrogencarbonate or sodium hydride is more preferred. The base may be used in an amount of from 1 to 1 moles per mole of the compound of the formula (VI), preferably from 1 to 3 moles. The leaving group L 1 is not particularly limited as long as it can be used for the reaction, and it may be, for example, a halogen or a toluenesulfonyl group. As the reaction initiator, one or more kinds selected from the group consisting of, for example, sulfurous acid, sulfite and Rongalit (formaldehyde, sodium sulfate) can be used. The reaction initiator can be used in an amount of 0.05 to 5 moles per mole of the compound of the formula (VI) or (XIV), preferably 〇·ι to 丨.2 mole multiple. The reaction of the method [5] can usually be carried out in the presence of a solvent. As the solvent, one or more suitable ones selected from, for example, ethers such as diethyl ether, butyl methyl ether, tetrahydrofuran, dioxane and dimethoxyethane; halogenated hydrocarbons such as chlorobenzene, dichlorobenzene, and the like Methyl chloride, chloroform, carbon tetrachloride, dichloroethane 'trichloroethane and dichloroethylene; aromatic hydrocarbons such as benzene, toluene and xylene; aliphatic hydrocarbons such as pentane, hexane, gly Alkane, octane and cyclohexyl; polar aprotic solvents such as acetonitrile, propionitrile, N,N-dimethylformamide, -15-201127291 N,N-dimethylacetamide, dimethyl Anthraquinone, tridecyl hexamethyl phosphate, cyclobutyl hydrazine and N-methyl-2-pyrrolidone; and water. The reaction of the method [5] can be carried out usually in the reaction system at -40 ° C to reflux temperature, preferably at 0 ° C to 100 ° C, and the reaction time is usually about 10 to 24 hours, preferably about 0.5 to 20 hours. The compound of the formula (XIV) can be obtained by subjecting the compound of the formula (VI) to a conventional method. The compound of the formula (VI) and the compound of the formula (XIV) are mutually converted by an oxidation reduction reaction, and the compound of the formula (VI) can be easily oxidized by oxygen in the air to form a compound of the formula (XIV). Method [6]

R4 (1-0 R4 (Ig) In the above formula, R1, R3, R4 and R5 are as defined above, and Q is a benzene ring or a pyridine ring. Process [6] is a method for producing a compound of the formula (Ig) , which comprises reducing a compound of the formula (If) and will be described in detail. The reduction reaction of the method [6] is a reaction of a compound of the formula (If) with a reducing agent, and the reduction reaction can be, for example, the following catalytic hydrogenation reaction, or by The reduction reaction of a metal or a metal salt can be carried out to obtain a compound of the formula (Ig). The reducing agent used for the catalytic hydrogenation reaction is hydrogen. The catalytic hydrogenation reaction can usually be carried out in the presence of a catalyst and a solvent. It may be one or more suitable from -1627 to 201127291, selected from the group consisting of pin carbon, Raney nickel and cerium oxide. The amount of catalyst may be 0.0001 to 1 〇 mole multiple relative to the compound of the formula (If). It is preferably 0.001 to 1 mol. The solvent is not particularly limited 'as long as it can be used for the reaction, and may be one or more suitable selected from, for example, ethers such as diethyl ether, butyl methyl acid, tetrahydrofuran, dioxane and Methoxyethane; aromatic hydrocarbons such as benzene , toluene and xylene; aliphatic hydrocarbons such as pentane, hexane, heptane, octane and cyclohexyl; polar aprotic solvents such as acetonitrile, propionitrile, N,N-dimethylformamide, N , N-dimethylacetamide, dimethyl hydrazine, tridecyl hexamethyl phosphate, cyclobutyl hydrazine and N-methyl-2-pyrrolidone: alcohols such as methanol, ethanol, n-propanol , isopropanol, n-butanol and tert-butanol: organic acids such as acetic acid and propionic acid; esters such as methyl acetate and ethyl acetate; and pyridines such as pyridine and picoline. It can be carried out at -2 to 150 ° C, preferably at 〇 to 1 〇〇 ° C ' and the reaction time is usually from about 30 minutes to about 48 hours, preferably from about 1 to 24 hours. The reducing agent for the reduction reaction of the metal or metal salt is a metal or metal salt ' and may be one or more suitable selected from, for example, zinc, tin, tin chloride, iron, etc. The amount of the metal or metal salt relative to the formula (compound may It is a multiple of 1 to 100 moles, preferably 1 to 10 moles. The reduction reaction by metal or metal salt can be present in acid or base. It is carried out as needed. As the acid, one or more suitable ones may be selected, for example, from organic acids such as acetic acid and propionic acid; and inorganic acids such as hydrochloric acid, sulfuric acid and phosphoric acid. As the base, one or more suitable ones may be selected. From, for example, alkali metal-17-201127291 hydroxides such as sodium hydroxide and potassium hydroxide; and alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide. The amount of acid or base may be relative to the compound of formula (If) 0.1 to 1,000 moles, preferably 1 to 100 moles. The reduction by metal or metal salt can be usually carried out in the presence of a solvent. The solvent is not particularly limited as long as it can be used for the reaction, and for example, the foregoing can be used. The catalytic hydrogenation reaction is exemplified. Furthermore, in addition to the above, one or more suitable ones may be selected, for example, from halogenated hydrocarbons such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane, trichloroethane. And dichloroethylene; and water. The reaction of the method [6] can be carried out usually at -50 to 150 ° C, preferably at -10 to 100 ° C, and the reaction time is usually about 30 minutes to 48 hours, preferably about 1 to 2 4 hour. [Method of Producing Intermediate] The compound of the formula (VI) which is the starting material of the method [5] can be obtained, for example, by a three-step reaction, and comprises (1) the first step of the compound of the formula (VIII) and the formula (IX). The compound is subjected to a coupling reaction to obtain a compound of the formula (X) '(2), the second step is a method of applying a halosulfonate to a compound of the formula (X) to obtain a compound of the formula (XI), and (3) a third step The compound of formula (XI) is reduced to give a compound of formula (VI). This method is described in detail below. In the following formula, R1, R2, R3 and R4 are as defined above, and X is a halogen. -18 - 201127291 R1 乂?" B(OH)2 r3〇二R1 r2^Vn halosulfonated R1 N-/ RzA HR f reduction, r3ttS Η4 V R4 (X) ''t>s〇—Vs ( VIII) (IX) R4 (xi) R4 (VI) The coupling reaction is usually carried out in the presence of a copper catalyst. The copper catalyst can be any copper catalyst 'as long as it can be used to carry out the coupling reaction, and can be one or more suitable ones selected from, for example, copper (metal copper), copper (II) sulfate, copper (I) sulfate, copper oxide ( II), copper (I) oxide, copper (II) chloride, copper (I) chloride, copper (II) acetate and copper (I) acetate. The amount of the copper catalyst may be 0.001 to 1 mole, and preferably 0.01 to 0.5 mole, relative to the compound of the formula (X). The coupling reaction can be carried out in the presence of a base and a solvent, as the case requires. As the base, the same as the step [1-2] of the method [1] can be used. The base may be used in an amount of 0.1 to 10 moles, more preferably 1 to 2 moles, per mole of the compound of the formula (VIII). The solvent is not particularly limited 'as long as it can be used for the reaction, and may be one or more suitable selected from, for example, ethers such as diethyl ether, butyl methyl ether, tetrahydrofuran, dioxane and dimethoxyethane; aromatic hydrocarbons , such as benzene, toluene and xylene; aliphatic hydrocarbons such as pentane, hexane 'heptane, octane and cyclohexane; and polar aprotic solvents such as acetonitrile, propionitrile, N,N_: methylformamidine Amine, N,N-dimethylacetamide, dimethyl hydrazine, tridecyl hexamethyl phosphate, cyclobutyl hydrazine and N-methyl-2-pyrrolidone. The coupling reaction can usually be carried out in a reaction system at a temperature of from 〇C to reflux, preferably at t to 150 ° C, and the reaction time is usually from about 1 to 30 hours. The halosulfonation reaction can be carried out in the presence of a halosulfonating agent. As the sulphuric acid "19-201127291 oximation agent, one or more suitable ones selected from, for example, a halogen sulfonic acid compound such as chlorosulfonic acid and bromosulfonic acid can be used. Among these sulfonating agents, chlorosulfonic acid is preferably used. The halosulfonating agent can be used in an amount of from 1 to 100 moles, preferably from 1 to 10 moles, per mole of the compound of the formula (X). The halosulfonation reaction can be carried out in the presence of a solvent, as the case requires. The solvent is not particularly limited as long as it can be used for the reaction, and may be one or more suitable ones selected from, for example, ethers such as diethyl ether, butyl methyl ether, tetrahydrofuran, dioxane, and dimethoxyethane; halogenated hydrocarbons, Such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane, trichloroethane and dichloroethylene; aliphatic hydrocarbons such as pentane, hexane, heptane, octane And cyclohexane; and organic acids such as acetic acid and propionic acid. The halosulfonation reaction can be carried out usually in the reaction system at -10 ° C to reflux temperature, preferably at 10 ° C to 15 Torr. (: proceeding, and the reaction time is usually about 1 to 48 hours, preferably about 1 to 24 hours. The reduction reaction can be carried out in the presence of a reducing agent. As the reducing agent, one or more suitable ones selected from, for example, metals Compounds such as zinc, tin and iron; pity compounds such as red phosphorus and triphenylphosphine; and halogen compounds such as potassium iodide and iodine. The reducing agent can be used in an amount of from 1 to 1 mole per mole of the compound of formula (XI). The multiple is preferably 1 to 10 moles. The reduction reaction may be carried out in the presence of an acid, as the case requires. As the acid, one or more suitable ones may be selected, for example, from inorganic acids such as hydrochloric acid, sulfuric acid, nitric acid and phosphoric acid: Lewis acids such as aluminum chloride and polyphosphoric acid; organic acids such as acetic acid and propionic acid; and solid acids such as montmorillonite K-io. The acid can be used in an amount of 0066 to 200 moles relative to the compound of formula (XI). Ear multiplier, -20- 201127291 is preferably 2 to 20 moles. The reduction reaction may be carried out in the presence of a solvent, as the case requires. The solvent is not particularly limited 'as long as it can be used for the reaction, and may be one or more suitable choices Self-example Ethers such as diethyl ether, butyl methyl ether, tetrahydrofuran, dioxane and dimethoxyethane; aromatic hydrocarbons such as benzene, toluene and xylene: aliphatic hydrocarbons such as pentane, hexane 'g Alkanes, octanes and cyclohexanes; alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol; and nitriles such as acetonitrile and propionitrile. Reduction reaction usually at 0 °c to reflux temperature in the reaction system is preferably '0 ° C to 1 000. (:: and the reaction time is usually about) to 48 hours, preferably about! ~ 24 hours. The compound of the formula (X) which can be obtained by the first step (1) of the method for producing an intermediate can also be obtained by the following method [A] or [B].

In the method [A], R1 '· R2, R3 and R4 are as defined above. Process [A] is a process for producing a compound of the formula (X) which comprises reacting a compound of the formula (χΠ) with a compound of the formula (III) to give a compound of the formula (XIII), which is subjected to a dehydrogenation reaction' and comprises the aforementioned step A- 1 and A-2. The method [A] can be carried out in accordance with the aforementioned method [1]. -21 - 201127291 Method [B]

R4 (XII) R4 (X) In the method [B], R1, R2, R3 and R4 are as defined above. Process [B] is a process for producing a compound of the formula (X), which comprises reacting a compound of the formula (XII) with a compound of the formula (V). The method [B] can be carried out in accordance with the aforementioned method [2]. The compound which is the starting material of the above-mentioned method [A] or [B] can be produced, for example, according to the following method [C]. Method [C1 [C]

In the method [C], 'R1, R3 and R4 are as defined above. Process [c] is a process for producing a compound of the formula (XII), which comprises reacting a compound of the formula (XV) with a compound of the formula (X VI ) to give a compound of the formula (XV π), which is converted to give the formula (X ν ) 111) A compound which further reacts a compound of the formula (XV) to an aqueous ammonia solution, and which comprises the aforementioned steps Cd, C-2 and C.3. In this case, in the aforementioned step c-1, the compound of the formula (xVI) can be substituted with the acetal form or the hemiacetal form of the compound of the formula (XVI) in 201127291. The individual reaction steps are described in detail. The reaction of the step C-1 can be carried out in the presence of an acid, as the case requires. The acid ' may be one or more suitable selected from the group consisting of acetic acid, hydrochloric acid, sulfuric acid, methanesulfonic acid, p-toluenesulfonic acid and the like. The acid amount may be 0.05 to 2 moles per mole of the compound of the formula (XV), preferably 〇.! to! Mohr multiples. The compound of formula (XV) can be a salt. When a salt of the compound of the formula (XV) is used, the reaction of the step C-1 can be carried out in the presence of a base, as the case requires. As the base, one or more suitable ones may be selected, for example, from alkali metal carbonates such as sodium carbonate and potassium carbonate; alkali metal hydrogencarbonates such as sodium hydrogencarbonate and potassium hydrogencarbonate: acetates such as sodium acetate and potassium acetate; And an organic base such as triethylamine and hydrazine. The reaction of step C-1 can usually be carried out in the presence of a solvent. The solvent is not particularly limited as long as it can be used for the reaction, and the same as the reduction reaction used in the aforementioned "method for producing an intermediate" can be used. The reaction of the step C-1 can be carried out usually in the reaction system at -70 ° C to reflux temperature, preferably -20 ° C to 150 ° C, and the reaction time is usually about 1 minute to 24 hours, preferably. It takes about 30 minutes to 12 hours. The halogenation reaction of the step C-2 can be carried out in the presence of a halogenating agent. As the halogenating agent, it may be one or more suitable selected from, for example, chlorine, bromine, chloramine, N-chloroammonium imine, N-bromosinium imine, hypochlorous acid and tert-butyl hypochlorite. After the reaction of the step C-1, the reaction of the step C-2 can be carried out continuously after the isolation of the obtained (χνπ) compound or without isolation. When the compound of the formula (XVII) is isolated, the anti--23-201127291 reaction of the step C-2 can usually be carried out in the presence of a solvent. The solvent is not particularly limited as long as it can be used for the reaction, and the same as the coupling reaction used in the aforementioned "method for producing an intermediate" can be used. The halogenation reaction of the step C-2 can be carried out usually in the reaction system at -7 (TC to reflux temperature, preferably -20 ° C to 150 ° C, and the reaction time is usually about 10 minutes to 24 hours, preferably. The reaction is carried out for about 30 minutes to 12 hours. The reaction of the step C-3 can be usually carried out in the presence of a solvent. The solvent is not particularly limited as long as it can be used for the reaction, and may be one or more suitable ones selected from, for example, ethers such as diethyl ether. , butyl methyl ether, tetrahydrofuran, dioxane and dimethoxyethane; halogenated hydrocarbons such as chlorobenzene 'dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane, trichloroethane And dichloroethane: aromatic hydrocarbons such as benzene, toluene and xylene; aliphatic hydrocarbons such as pentane, hexane, heptane, octane and cyclohexane; polar aprotic solvents such as acetonitrile, propionitrile , N,N-dimethylformamide, hydrazine, hydrazine-dimethylacetamide, dimethyl hydrazine, trimethylamine hexamethylphosphate, cyclobutyl hydrazine and hydrazine-methyl-2-pyrrolidine Ketone; water; esters such as methyl acetate and ethyl acetate; ketones such as acetone, methyl ethyl ketone and cyclohexanone; and pyridine, such as The reaction of the pyridine and the methylpyridinium in the step C-3 can be carried out usually in the reaction system at a temperature of from -30 ° C to the reflux temperature, preferably from -10 ° C to 1 ° ° C ' and the reaction time is usually about 10 minutes to 24 hours, preferably about 30 minutes to 12 hours. Specific embodiments of the insecticide, acaricide, nematicide or soil pesticide containing the compound of the present invention are described below. Insecticides, acaricides, nematicides or soil pesticides can be used, for example, as insects, mites, nematodes or soil pests that cause problems in farms and horticultural fields, ie as agricultural and horticultural insecticides. Agent, acaricide, nematicide or soil pesticide or as an agent for controlling parasitic insects or mites on animals, that is, as an agent for controlling parasites in animals. The compound of the present invention can be used as an agricultural and horticultural insecticide, acaricide , nematicides or soil pesticides. In particular, it is effective against insects such as mites such as 'Myzus persicae and Aphis gossypii', agricultural insect pests such as Plutella xyllis (Plutella x) Ylostella), Mamestra brassicae, Spodoptera litura, Cydia p〇mοne 11 a, Heliothis zea, Heliothis virescens, Lymantria dispar ), Cnaphalocrocis medinalis, Adoxophyes sp., Leptinotarsa decemlineata, Aulacophora femoralis, Anthonomus grandis, locust, leaf蝉, scale insects, beetles, whiteflies, thrips, locusts, anthomyiid flies, chafers, Agrotis ipsilon, Agrotis segetum and grasshoppers; gastropods such as scorpion And snails; hygienic insect pests such as tropical rat touches (Ornithonyssus bacoti), cockroaches, Musca domestica and Culex pipiens; storage of cereal insects such as Sitotroga cerealella, Callonomy (Callosobruchus) Chinensis ), T rib ο 1 iumcastaneum and Tenebrio molitor; Such as Tinea pellionella, Attagenus japonicus and subterranean termites; 螨, such as plants-25- 201127291 parasitic mites, such as Tetranychus urticae, Tetranychus cinnabarinus, Tetranychus kanzawai, Panonychus citri, Panonychus ulmi, Polyphagotarsonemus latus, A cu 1 ops pelekassi and root 螨Rhizoglyphus echinopus); and domestic transmissions, such as Tyrophagus putrescentiae, Dermatophagoids farinae, Chelacaropsis mo or ei; nematodes, such as plant-parasitic nematodes, such as nodule nematodes, cystic nematodes , root rot nematodes, Aphelenchoides besseyi, Nothotylenchus acris and Bursaphelenchus xylophilus; and soil pests such as isopods such as Armadillidium vulgare and balls Chaos (Porcellio scaber). Among them, agricultural and horticultural insecticides, acaricides, nematicides or soil pesticides containing the compound of the present invention are particularly effective for the prevention of plant parasitic mites, agricultural insect pests, plant parasitic nematodes or the like. In particular, it can more effectively control plant parasitic mites and agricultural insect pests, and thus can be used as an insecticide or an acaricide. In addition, it is effective against insect pests that have acquired resistance to organophosphorus, urethane, pyrethroid and/or neonicotinoid insecticides. Moreover, the compound of the present invention has excellent system properties, and by applying the agricultural and horticultural insecticide containing the compound of the present invention to soil treatment, it can not only control harmful insects, harmful cockroaches, harmful nematodes, harmful gastropods and harmful substances in the soil. Foot animals can also control leaf pests. -26- 201127291 Another preferred embodiment of an insecticide, acaricide, nematicide or soil pesticide containing a compound of the invention may be an agricultural and horticultural insecticide, an acaricide, a nematicide or a soil Pesticides, which prevent the above-mentioned plant parasitic cockroaches, agricultural insect pests, plant parasitic nematodes, gastropods and soil pests as a whole. Agricultural and horticultural insecticides, acaricides, nematicides or soil pesticides containing the compounds of the invention are usually formulated by mixing the compounds with various agronomic adjuvants and are used in the form of formulations such as powders, granules, water - dispersible granules, wettable powders, water-based suspension concentrates, oil-based suspension concentrates, water-soluble granules, water-soluble powders, emulsifiable concentrates, soluble concentrates, pastes, aerosols Or ultra low volume formulations. However, as long as it is suitable for the purpose of the present invention, it can be formulated to be any type of formulation generally used in the field. Such agronomic adjuvants include solid carriers such as diatomaceous earth, calcium carbonate, talc, white carbon, kaolin, bentonite, kaolin, sericite, clay, sodium carbonate, sodium hydrogencarbonate, thenardite 'zeolite and starch; solvent, Such as water, toluene, xylene, solvent naphtha, dioxane, acetone, isophorone, methyl isobutyl ketone, chlorobenzene, cyclohexane, dimethyl hydrazine, hydrazine, hydrazine - dimethyl Mercaptoamine, N,N-dimethylacetamide, N-methyl-2-pyrrolidone and alcohol; anionic surfactants such as fatty acid salts, benzoates, alkyl sulfo amber Acid salt, sulfosuccinate, dialkyl sulfosuccinate, polycarboxylate, alkyl sulfate salt, alkyl sulfate, alkyl aryl sulfate, alkyl diglycol ether sulfate Alcohol sulfate salt, alkyl sulfonate, alkyl aryl sulfonate, aryl sulfonate, lignosulfonate, alkyl diphenyl ether disulfonate, polystyrene-6-201127291 Alkene sulfonate, alkyl phosphate salt, alkyl aryl phosphate, phenylethyl aryl phosphate, polyethylene oxide alkyl ether sulfate Salt, polyethylene oxide alkyl aryl ether sulfate, polyethylene oxide alkyl aryl ether sulfate salt 'polyethylene oxide alkyl ether phosphate, polyethylene oxide alkyl aryl a salt of a phosphate ester and a salt of a naphthalene sulfonate and a formaldehyde condensate; a nonionic surfactant such as a sorbitan fatty acid ester, a glycerin fatty acid ester, a fatty acid polyglyceride, a fatty acid alcohol polyglycol ether, an acetylene II Alcohol, acetylene alcohol, alkylene oxide block polymer, polyethylene oxide alkyl ether, polyethylene oxide alkyl aryl ether, polyethylene oxide styryl aryl ether, polyethylene oxide Glycol alkyl ether, polyethylene glycol, polyethylene oxide fatty acid ester, polyethylene oxide sorbitan fatty acid ester, polyethylene oxide glycerin fatty acid ester, polyethylene oxide hydrogenated castor oil And polypropylene oxide fatty acid esters; plants and mineral oils such as olive oil, kapok oil, castor oil, palm oil, camellia oil, coconut oil, sesame oil, corn oil, rice bran oil, peanut oil, cottonseed oil, rapeseed Oil, linseed oil and liquid paraffin, etc. The individual components of the adjuvant may be one or more appropriately selected users as long as the object of the present invention can be attained. Further, adjuvants other than the aforementioned additives may be appropriately selected, some of which are known in the art. For example, various adjuvants which are generally used, such as a tanning agent, an encapsulating agent, an anti-settling agent, an antifreeze agent, a dispersion stabilizer, a phytotoxicity reduction||, an antifungal agent, etc. can also be used. The weight ratio of the compound of the present invention to various agronomic adjuvants is 0.001:99.999 to 95:5, preferably 0.005:99.995 to 90:10. In the practical application of the formulation, it may be diluted to a predetermined concentration in the original form, or may be diluted with a diluent such as water, and may be added to various exhibiting agents according to the conditions of 1f-28-201127291. For example, surfactants, vegetable oils or mineral oils. The application of agricultural and horticultural insecticides, acaricides, nematicides or soil pesticides containing the compounds of the invention cannot be defined as such, depending on the climatic conditions, the type of formulation, the season of application, the site of application or the outbreak of insect pests Change in degree. However, usually the active ingredient is applied at a concentration of from 0.05 to 800,000 ppm, preferably from 0.5 to 500,000 ppm, and the dosage per unit area is such that the compound of the present invention is from 0.05 to 50,000,000 grams per hectare. The best is 1 to 3,000 grams per hectare. Furthermore, the present invention encompasses such a method of controlling insects, mites, nematodes or soil pests, particularly for controlling plant parasitic mites, horticultural insect pests or plant parasitic nematodes. The insecticide, acaricide, nematicide or soil pesticide or a diluted composition thereof containing the compound of the present invention can be applied by a conventionally applied application method such as spraying (for example, spraying, spraying, atomizing, powder or The particles are spread or dispersed in water), applied (eg mixed or soaked) by the soil, applied (eg coated, dusted or covered) or impregnated to obtain a toxic feed. Further, the food containing the aforementioned active ingredient can be used to feed the livestock and control the outbreak or growth of the excrement pests, especially insect pests. Further, the active ingredient can also be applied by a so-called ultra low volume application method. In this method, the composition may consist of 1% active ingredient. In addition, agricultural and horticultural insecticides, acaricides, nematicides or soil pesticides containing the compounds of the invention may be combined or combined with other horticultural chemicals, fertilizers or phytotoxicity reducing agents, sometimes with synergistic effects or active. Such other agrochemical chemicals include, for example, herbicides, insecticides, -29-201127291 elixirs, nematicides, soil insecticides, fungicides, antivirals, attractants, antibiotics, phytohormones, plant growth Conditioner and so on. In particular, mixing or combining an insecticide, acaricide, nematicide or soil pesticide having a compound of the invention with an active compound of one or more other agrochemical chemicals allows for application range, application time, insecticidal activity, etc. Improve in the better direction. The compounds of the present invention and the active compounds of other agrochemical chemicals can be formulated separately such that they can be mixed at the time of application or they can be formulated together. The present invention includes such insecticides, acaricides, nematicides or soil pesticide compositions. The mixing ratio of the compound of the present invention relative to the active compound of other horticultural chemicals cannot be defined as it varies depending on the climatic conditions, the type of formulation, the time of application, the site of application, the type or extent of the outbreak of insect pests, etc., but usually It is in the range of 1:300 to 30,000:1 by weight, preferably 1:100 to 100:1. Further, the dosage is administered such that the total amount of the active compound is from 0.1 to 5 Å, preferably from 1 to 30,000 g/ha. The present invention includes a method of controlling insects, mites, nematodes or soil pests by applying the insecticide, acaricide, nematicide or soil pesticide composition. The aforementioned insect pest control agents (such as insecticides, killers, nematicides, or soil-killing insecticides) in the horticultural chemicals include, for example, (using the common name 'some of which are still in the application stage, or the Japan Plant Protection Association) Test code): Organic dish vinegar compound, such as breamone (pr〇fen〇f〇S), dichlorvos, fenamiphos, fenitrothion, EPN, dinitrogen Diazinon, taosson (-30- 201127291 chlorpyrifos), taosson-methyl ester, acephate, prothiofos, cadusafos, dislufoton, plusfusone Isoxathion ), isofenphos, ethion, etrimfos, quinalphos, dimethy 1 vi np h 〇s Dimethoate, sulprofos, thiometon, vamidothion, pyraclofos, pyridaphenthion 'pirimiphos-m Ethyl), propaphos, phosalone, formothion, malathion, tetrachlorvinphos, chlorfenvinphos, cyanophos, Trichlorfon, methidathion, phenthoate, ESP, azinphos-methyl, fenthi ο η, heptenophos, chlorinated methanol (methoxychlor), parathion, phosphocarb, demeton-S-methyl, monocrotophos, methamidophos, imicyaf〇 s), methyl balason, terbufos, ph〇sphamid〇n, ph 〇smet and ph 〇rate; urethane compounds, Such as carbaryl, propoxur, aldicarb, carb〇furan, thiodicarb, methomyl, octopus-31 - 201127291 (oxamyl), ethiofencarb, Pontimicarb, fenobucarb, carbosulfan, benfuracarb, bendiocarb, furathiocarb, isoprocarb Isoprocarb), metolcarb, xylylcarb, XMC and fe η othiocarb; silkworm toxin derivatives such as cartap, thiocycl am, exempt Bensultap and thiosultap-sodium; organochlorine compounds such as dicofol, tetradi fon, endosulufan, dienochlor and Dieldrin; organometallic compounds such as fenbutatin oxide and cyhexatin; pyrethroids such as fenvalerate, permethrin, cypermethrin Cypermethrin ) 'deltamethrin, cyhalothrin, tefluthrin, etho fenpr ο x, flufenprox, cyfluthrin ( c Yfluthrin ), fenpropathrin, flucythrinate, fluvalinate, cycloprothrin, lambda-cyhalothrin, de-worming Pyrethrins, esfenvalerate, tetramethrin, resmethrin, promethrin (-32- 201127291 protrifenbute), bifenthrin, cypermethrin vinegar (zeta-cypermethrin), arvinthrin, alpha-cypermethrin, al 1 ethri η , y-cyhalothrin, 0-cypermethrin, fluocin Tau-fluvalinate, trolomethrin, profluthrin, 3-cypermethrin, cyhalothrin, metofluthrin, fenfluthrin Phenothrin) and flumethrin; benzamidine urea compounds, such as diflubenzuron, chlorfluazuron, teflubenzuron, flufenoxuron, lufenlong Lufenuron), Valentin (novaluron), triflumuron, hexaflumuron, bistrifluron, noviflumuron, and fluzuron; juvenile hormones such as beauty Metoprene, pyriproxyfen, fenoxycarb, and diofenolan; chlorpyrifos compounds, such as pyridaben; oral oxime compounds, such as Fenpu Contact (fenpyroximate), fipronil, H. tebufenpyrad, ethiprole, tο 1 fenpyrad, acetoprole, bismuth nitrile ( Pyrafluprole) and pyriprole; neonicotinoids such as imidacloprid, nitenpyram-33-201127291 (nitenpyram), acetamiprid, thiacloprid , thiamethoxam, thiamethoxam, c 1 〇thianidi η , nidi η 〇tefura η, di η 〇tefura η and nithiazine; bismuth compounds such as fenfen Connaught Ebufenozide), methoxyfenozide, chromafenozide and halofenozide; shame compounds such as pyridaryl and flonicamid; cyclic ketones - a suspected alcohol compound such as spirodiclofen; spiromesifen, spirotetramat; a strobilurin compound such as fluacrypyrim; a pyridinamine compound such as flufensulfonate ( Flufenerim): dinitro compounds; organic sulfur compounds; urea compounds; triterpenoids; antimony compounds; other compounds such as buprofezin, hexythi azox, amitraz, insecticidal ( chlordimeform ), silafluofen, triazamate, pymetrozine, pyrimidifen, ch 1 orfenapyr, indoxacarb, sub Ace (acequinocyl), etoxazole, cyromazine, 1,3-dichloropropene diafenthiuron, benclothia z), biphenyl hydrazine-34- 201127291 (bifenazate), prop ar gite, clofentezine, metaflumizone, flubendiamide, butylated fluoroester ( Cyflumetofen), chlorantraniliprole, cyenopyrafen, pyrifluquinazon, fenazaquin, amidoflumet, sulfluramid, amesone ( hydramethylnon ), metaldehyde, HGW 86, ryanodine, and verbutin; and the like. In addition, it can be used in combination or together with the following components: microbial agrochemicals, such as Bacillus thuringiensis aizawai, kurstaki strain Bacillus thuringiensis kurstaki, 以! j variant Suli Bacillus thuringiensis israelensis, B aci 11 ust hur in gi en sis japonensis, Bacillus thuringiensis tenebrionis or Bacillus thuringiensis, insect virus, insect Insect crystallized protein produced by fungi (etomopathogenic fungi) and nematophagous fungi (nematophagous fungi); antibiotic or semi-synthetic antibiotics such as avermectin, emamectin-benzoic acid vinegar, rice Milbemectin, milbemycin, spinosad, ivermectin, lepimectin, DE-175, abamectin, y Emamectin and spinetoram; natural products such as azadirachtin and venom ( Rotenone); and repellents, such as enemies (deet-35-201127291, the other active ingredients of fungicides in other horticultural chemicals, including, for example, (using common names, some of which are still in the application stage, or the Plant Protection Association) Test code): an anilino-based chewing compound such as mepanipyrim, pyrimethanil, and cyprodinil; triazoropyrimidine compound, such as 5-chloro -7-(4-Methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl) [1,2,4]triazolo[1,5-a]pyrimidine; pyridine Amine compounds, such as fluazinam; azole compounds such as triadimefon, bitertanol, triflumizole, etaconazole, propiconazole , penconazole 'flusilazole, myclobutanil, cyproconazole, tebuconazole, hexaconazole, furfurazol e- Cis ), prochloraz, mute (m Etconazole ), epoxiconazole, tetraconazole, oxpoconazole fumarate, sipconazο 1 e, prothioconazole, triterpene Triadimenol, flutriafol, difenoconazole, fluquinconazole, fenbuconazole, bromuconazole, diniconazole, Tricyclic 哗 ( -36- 201127291 tricyc 1 a ζ ο 1 e ), propyl benzophenanthrene (pr 〇bena ζ ο 1 e ), simeconazole, pefurazoate, inoculum 13⁄4 (ipconazole And imibenconazole; sulphonate compounds, such as quinomethionate; dithiocarbamate compounds, such as maneb, zineb, daisen Zinc (mancozeb), polyamine-based Shen vinegar, metiram, propineb and thiram; organochlorine compounds such as fthalide, tetrachlorobenzene (benzene) Chlorothhalonil) and pentachloronitro Benzene (quintozene); imipenem compounds, such as benomyl (benomyl), cyanofamid, thiophanate-methyl, carbendazim, thiabendazole ) and fuberiazole; cyanoacetamide compounds, such as cymoxanil; phenyl guanamine compounds, such as metalaxyl, metalaxyl-M, fine armor Mefenoxam, oxadixyl, ofurace, benaxyl, benalaxyl-M (alias: kiralaxyl, Cressi) (chiralaxyl)), furalaxyl, cyprofuram, carboxin, oxycarboxin, thifluzamide, boscalid, Bixafen, isotianil, tiadinil, and sedaxane; -37- 201127291 Sulfonamide compounds, such as diflulofluanid; copper compounds, such as hydrogen Copper oxide and copper hydroxyquinolate; isoxazole compounds, such as carbendazim Organic phosphorus compounds such as triethylphosphonic acid-A1, tolclofos-methyl, 0,0-diisopropyl-thiophosphoric acid S-vinegar, S,S-diphenyldithiophosphate Ο-ethyl ester, ethyl aluminum hydrogenphosphonate, edifenphos and iprobenfos; benzoquinone imine compounds such as captan, captafol and sterilization Folpet; a dimethyl quinone imine compound, such as a procymidone, an iprodione, and a vinclozolin; a benzoquinone compound such as flutolanil And mepronil; guanamine compounds, such as penthiopyrad, 3-(difluoromethyl)-1-methyl-chuan (1113, 4311, 931〇-1, 2, 3, 4-tetrahydro-9-isopropyl-1,4-methylenenaphthalen-5-yl]pyrazole-4-carboxamide and 3-(difluoromethyl)-bumethyl-N-[(1RS, 4SR,9SR) -1,2,3,4-tetrahydro-9-isopropyl·1,4-methylenenaphthalen-5-yl]lazen-4-carboxamide mixture (isopyrazam), sand Silthiopham and fenoxanil; benzoic acid amine compounds such as fluopyr Am ) and oxazolamide (ζ ο X amide ); piperidine compounds such as triforine; pyridine compounds such as pyrifenox; ortho alcohol compounds such as chloramphetamine (fenarimol) -38- 201127291 piperidine compounds, such as fenPr〇Pidine; morpholine compounds such as fenpromorph (h) and decanomorph; organotin compounds such as triphenylhydrogen Fetin hydroxide and fentin acetate; urea compounds such as pencycuron; cinnamic acid compounds such as dimethomorph and flumorph; phenyl A urethane compound, such as diehofencarb; a cyanopyrrole compound, such as fludioxonil and fenpiclonil; a strobilurin, such as azoxystrobin , kresoxim-methyl, metominofen, trifloxystrobin, picoxystrobin, oryzastrobin, & dimoxystrobi n), pyraclostrobin and fluoxastrobin; oxazolidinone compounds, such as famoxadone; thiazolylamine compounds, such as ethaboxam; amidoxime Compounds such as iprovalicarb and benthiavalicarb-isopropyl; thiol amino acid compounds such as hydrazine (isopropoxycarbonyl)-L-nonylamine thiol (3RS) -3-(4-chlorophenyl)-lu-alanine methyl ester (-39- 201127291 valiphenalate); an imidazolinone compound such as fenamidone; a hydroxyaniline compound such as fenhexamid a benzenesulfonamide compound, such as sulfsulfamide; a compound of the month 5, such as cyflufenamid; an anthraquinone compound; a crotonic acid compound; an antibiotic such as validamycin, jia Kasugamycin and scleromycin (p0ly0Xins); hydrazine compounds such as iminoctadine and dodine; sputum compounds such as 6-t-butyl-8-fluoroacetate 2,3-dimethylsporphyrin-4- (tebufloquin); thiazolidine compound, such as 2-[2-fluoro-5-(trifluoromethyl)phenylthio]-2-[3-(2-methoxyphenyl)thiazolidin-2-y Acetonitrile; and other compounds, such as pyribencarb, isoprothiolane, pyroquilon, diclomezine, quinoxyfen, hydrochloric acid Propamocarb hydrochloride, chloropicrin, dazomet, metam-sodium, nicobifen, metrafenone, UBF-307, double Diclocymet, proquinazid, amisulbrom (alias: amberromdole), pyridoxone (-40-201127291 pyriofenone), dipropionamide (mandipropamid) , fluopicolide, carpropamid, meptyldinocap, ferimzone, spiroxamine S-2 1 8 8 ), S-2200, ZF-9646, BCF-051, BCM-06 1 and BCM-062. Furthermore, agrochemicals which may be blended or used in combination with the compounds of the invention may, for example, be active ingredient compounds in herbicides, as disclosed in The Pesticide Manual, 14th edition, especially soil. Processing type. Insecticides against parasites in animals can effectively control, for example, harmful ectoparasites that are parasitic on the surface of the host animal (such as the back, armpits, lower abdomen or inner thigh) or parasitic on the host animal (such as the stomach, intestines, lungs) Harmful endoparasites in the heart, liver, blood vessels, subcutaneous tissue or lymphoid tissue, but are particularly useful for controlling ectoparasites. The ectoparasite can be, for example, an animal parasitic hair follicle or a mites. There are so many kinds that it is difficult to fully list them, so a typical example is listed. The animal parasitic hair follicles can be, for example, ticks, such as Boophilus microplus, Rhipicephalus sanguineus, long-horned blood clams. (H a em ap hysa 1 is longicornis ), Haemaphysalis flava, Haemaphysalis campanulata, Haemaphysalis concinna 'Haemaphysalis japonica, North Gang blood Haemaphysalis kitaokai, Haemaphysalis -41 - 201127291 ias, Ixodes ovatus, Ixodes nipponensis, Ixodes persulcatus, Amblyomma testudinarium ), giant blood stasis

Haemaphysalis megaspinosa), Dermacentor reticulatus and Dermacentor taiwanesis; Darmanyssus gallinae; northern fowl mite, such as Ornithonyssus sylviarum and tropical birds Nit (Ornithonyssus bursa ); trombiculidae, such as Eutrombicula wichmanni, Leptotrombidium akamushi, Leptotrombidium pallidum, Leptotrombidium fuji , Leptotrombidium tosa, Neotrombicula autumnalis, Eutrombicula alfreddugesi and Helenicula miyagawai; carnivorous contact, such as Cheyletiella yasguri, skin absorption虫 (C hey 1 etie 11 aparasitivorax ) and rabbit 螨 (Cheyletiella blakei); sarcoptic mange mite, such as Psoroptes cuniculi, Chorioptes bovis, deafness Worm (Otodectes cynotis), human touch (S arcoptessc a b i e i ) and cat mites (N o t o e d r e s c a t i ); and Demodicidae, such as Demodex canis. The insecticide containing the compound of the present invention against parasitic animals is particularly effective for controlling the above-mentioned niches. The animal parasitic mites may be, for example, an extracorporeal parasitic wingless insect belonging to the genus Hymenoptera (Siphonaptera - 42-201127291), especially a genus belonging to the genus Puli cidae, Ceratephyllus or the like. The genus belonging to the genus Aphididae can be, for example, a dog mites: (Ctenocephalides canis), Ctenocephalides felis, Pulex irritans, eggs (Echidnophaga gallinacea), Xenopsylla cheopis, 肓蚤: Leptopsylla segnis), European eggs (Nosopsyllus fasciatus) and unequal monophyls (Monopsyllus anisus). The insecticide containing the compound of the present invention against parasites in animals is particularly effective for controlling mites belonging to the family Aphididae, among which Ctenocephalides canis and Ctenocephalides felis ο other ectoparasites can be, for example Bloody (Anoplura), such as Haematopinus eurysternus, horse blood 13⁄4 (

Haematopinus asini), sheep worm, Linognathus vituli and Pediculus capitis; bristles 13⁄4, such as Trichodectes canis; and blood-sucking dipterous insects, such as insects (Tabanus trigonus) ), Taiwan snail (Culicoides schultzei) and scorpion (Simulium ornatum). In addition, the endoparasite can be, for example, a nematode such as a lung worm, a Trichuris, a tuberous worm, a stomach parasite, a mites, and a filaria; a locust, such as a snail scorpion (Spirometra erinacei) ), Diphyllobothrium latum, Dipylidium caninum, Taenia multiceps 'Echinococcus granulosus and multi-atrial hydatid (-43- 201127291)

Echinococcus multilocularis ); trematoda, such as Schistosoma japonicum and Fasciola hepatica; and protozoa, such as Plasmodium malariae Intestinal sarcocyst, toxoplasma and Cryptosporidium. The host animal can be, for example, a pet, a domestic animal, and a poultry, such as a dog, a cat, a mouse, a rat, a hamster, a guinea pig, a squirrel, a rabbit, a ferrets, a bird (such as a crane, a cockatoo, a cockroach, a clawed gull, a honey parrot). (honey parrot), love birds and canaries), cattle, horses, pigs, sheep, ducks and chickens. Insecticides containing the compounds of the present invention against parasites in animals are particularly effective in controlling parasitic pests that are parasitic on pet animals or domestic animals, particularly in the treatment of ectoparasites. It is particularly effective for dogs and cats, cattle and horses in dragon animals or livestock. When the compound of the present invention is used as an insecticide against parasites in animals, it may be used in its original state or may be formulated with various adjuvants to prepare various formulations such as powders, granules, lozenges, powders. , capsules, soluble concentrates, emulsifiable concentrates, water-based suspension concentrates and oil-based suspension concentrates. In addition to the formulations, it can be formulated into any type of formulation generally used in the art, as long as it is suitable for the purposes of the present invention. The adjuvant to be used in the formulation may, for example, be an anionic surfactant or a nonionic surfactant exemplified as an adjuvant for the formulation of agricultural and horticultural insecticides, acaricides, nematicides or soil pesticides. a cationic surfactant such as cetyltrimethyl-44-201127291 ammonium; solvent such as water, acetone, acetonitrile, N-methylacetamide, N,N-dimethylacetamidine Amine, N,N-dimethylformamide, 2-pyrrolidone, N-methyl-2-pyrrolidone, kerosene, triacetin, methanol, ethanol, isopropanol, benzyl alcohol, ethylene glycol, propylene glycol, Polyethylene glycol, liquid polyoxyethylene glycol, diethylene glycol monobutyl ether, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monoethyl ether, diethylene glycol Butyl ether, dipropylene glycol monomethyl ether or dipropylene glycol n-butyl ether; antioxidants such as butylated hydroxyanisole, butylhydroxytoluene, ascorbic acid, sodium metabisulfite, propyl gallate or thio Sodium sulfate; a film forming agent such as polyvinylpyrrolidone, polyvinyl alcohol or B Copolymer of vinyl ester and vinyl pyrrolidone; vegetable oil and mineral oil, as exemplified above for the formulation of agricultural and horticultural insecticides; carrier, such as lactose, sucrose, glucose, starch, flour, corn flour, large Okara and soybean meal, defatted rice bran, calcium carbonate or other commercially available feed; One or more of these adjuvants may be appropriately selected for use as long as the use does not deviate from the object of the present invention. Further, in addition to the aforementioned adjuvants, some of those known in the art may be suitably selected, and some of the aforementioned various adjuvants to be used in the agricultural and horticultural fields may be appropriately selected and used. The blending ratio of the compound of the present invention with respect to various adjuvants is usually from 0.1:99.9 to 90:10 by weight. In the actual use of such a formulation, it may be used in its original form, or may be diluted to a predetermined concentration using a diluent such as water and optionally added various spreading agents (eg, surfactants, vegetable oils). Or mineral oil). Administration of the compounds of the invention to a host animal is carried out orally or parenterally. As the oral administration method, a -45-201127291 lozenge, a liquid medicament, a capsule, a flake, a patties, a meat puree or other feed containing the compound of the present invention can be mentioned. As a parenteral administration method, for example, a method in which a compound of the present invention is formulated into a suitable formulation, and then administered to the body by, for example, intravenous administration, intramuscular administration, intradermal administration, subcutaneous administration, or the like can be mentioned. A method in which it is administered to a body surface by a spot coating treatment, a potting treatment or a spray treatment; or a method of embedding a resin fragment or a compound containing the compound of the present invention under the skin of a host animal. The dose of the compound of the present invention to the host animal varies depending on the administration method, the purpose of administration, the symptom reduction, and the like, but the usual administration ratio is 0.01 mg to 100 g per 1 kg of the host animal, preferably 0.1 mg to 10 g. . The present invention also encompasses a method for controlling pests by the aforementioned administration method or by the aforementioned dosage, particularly for controlling ectoparasites or endoparasites. Further, in the present invention, by controlling the aforementioned parasitic animal pests, various diseases of the host animal caused by the pest in some cases can be prevented or treated. Accordingly, the present invention also encompasses a prophylactic or therapeutic agent for an animal disease caused by a parasite comprising the compound of the present invention as an active ingredient, and a method for preventing or treating an animal disease caused by a parasite. When the compound of the present invention is used as an insecticide against parasitic animals in animals, various vitamins, minerals, amino acids, nutrients, enzymes, antipyretics, sputum agents, or the like may be used in combination or combination with an adjuvant. Anti-inflammatory agents, fungicides, colorants, aromatic substances, preservatives, and the like. In addition, depending on the situation, other animal drugs or horticultural chemicals, such as vitamins, anthelmintics, anticoccidial agents, insecticides, acaricides, miticides, nematicides, bactericides -46-201127291 Or antibacterial agents, which can be mixed or combined, sometimes with improved effects. The present invention includes a mixture of the above-mentioned various components in combination or in combination, and a method of controlling pests by using the composition, particularly a method for controlling ectoparasites or endoparasites. The present invention is now described as a preferred embodiment of the above formula ('). It is to be understood that the invention is in no way limited thereto. (1) A compound of the formula (I) or a salt thereof. (2) The aryltriazole derivative or a salt thereof according to the above (1), wherein R1 is an alkyl group which may be substituted by halogen; R2 is a phenyl group which may be substituted by X, or a pyridine which may be substituted by X X; is a halogen, an alkyl group, a haloalkyl group, an alkoxy group, a aryl alkoxy group, an alkylthio group, an amine group, a nitro group or a cyano group: each R3 and R4 are independent of each other and are hydrogen Atom, halogen, alkyl or cyano 'R5 is an alkyl group which may be substituted by A or an alkenyl group which may be substituted by A. (3) A aryltriazole derivative according to (2) or a salt thereof, wherein each of R and R4 is independently of each other and is a halogen, an alkyl group or a cyano group; and R5 is an alkyl group which may be substituted with A. (4) The aryltriazole derivative according to (2) or a salt thereof, wherein each of R and R4 is independently of each other and is a hydrogen atom, a halogen or an alkyl group; and R5 is an alkyl group which may be substituted by A. (5) The aryl-hydrazine derivative according to the above (1), (2), (3) or (4) or a salt thereof, wherein R2 is a pyridyl group which may be substituted by X. (6) The aryltriazole derivative or a salt thereof according to the above (5), wherein the X-substituted pyridyl group is a 2-pyridine group which may be substituted by an anthracene. (7) The aryltriazole derivative or a salt thereof according to the above (5), wherein the X-substituted pyridyl 2-pyridyl group is -47-201127291. (8) A salt according to the above (1) to (7), wherein n is ruthenium. (9) An insecticide, acaricide, nematicidal which comprises the diaryltriazole derivative as defined in the above (1) as an active ingredient. (1) The insecticide or the acaricidal soil pesticide according to the above (9), wherein the insecticide, the acaricide, and the killing line contain a diaryltriazole derivative or a salt thereof as an active ingredient and a horticultural use. (11) The agricultural and horticultural acaricide according to the above (10), which comprises a diaryltriazole derivative or a salt thereof (12), such as the insecticide or acaricide or acaricide of the above (9) , nematicide or soil pesticide containing two or a salt thereof as an active ingredient, for controlling animals (1 3) - controlling insects, mites, nematodes or soils comprising applying an effective amount as defined in the above (1) Or its salt. [Embodiment] Now, the present invention will be described in more detail with reference to the embodiments. First, a chemical example of the present invention will be described. A triazole derivative or agent or a soil pesticide, an organism or a salt thereof, a nematicide or insecticide or a soil pesticide, which is an insecticide for agricultural use or as an active ingredient. An agent wherein the insecticidal aryl triazole derivative is wormed or picked. The method of pests, the diaryltriazole is derived, but it should be understood that the preparation of the present compound is carried out -48-201127291 Preparation Example 1 2-(1-(2-fluoro-4-methyl-5-(2, Preparation of 2,2-trifluoroethylthio)phenyl)-3-(trifluoromethyl)-1H-1,2,4-triazol-5-yl)pyridine (Compound No. 32) 0.10 g Add p-toluenesulfonic acid monohydrate to 1.0 g of 2,2,2-trifluoro-fluorene-(2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio) a mixture of phenyl)acetamide (acetohydrazonamide), 0.34 g of 2-indene-sthamaldehyde and 20 mL of toluene, followed by heating under reflux for 1 hour by means of an azeotropic dehydration apparatus. The reactor was taken out from the oil bath and cooled to room temperature, after which a mixed solution of 0.59 g of triethylamine and 2 mL of toluene was added', followed by a reaction for 20 hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. Then, the organic layer was washed with water and an aqueous solution of sodium chloride, and anhydrous sodium sulfate was added to dry. The solvent was evaporated under reduced pressure and the residue was purified mjjjjjlililililililililili Preparation Example 2 Preparation of 2-(1-(2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulfonyl)phenyl)-3-(trifluoromethyl)- Preparation of 1H-1,2,4-triazol-5-yl)pyridine (Compound No. 34) 0.30 g of 3-chloroperbenzoic acid was added in three portions to 2-(1-(2-fluoro-) containing 0.18 g. 4-methyl-5(2,2,2-trifluoroethylthio)phenyl-3-(trifluoromethyl)-1 fluorene, 1,2,4-triazol-5-yl)pyridine (compound) In the mixed solution of No. 32) and 5 mL of chloroform, 'then reacted at room temperature for 24 hours. Add water -49-201127291 to the reaction solution, then extract with ethyl acetate. Then 'organic layer with sodium bicarbonate solution, water and The aqueous solution of sodium chloride was washed with the addition of anhydrous sodium sulfate to dryness. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography (solvent: n-hexane/ethyl acetate = 1/0 to 6/4) A solid of 0.11 g of the desired product was obtained. Preparation Example 3 2-(2-(2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl) Preparation of -3-(trifluoromethyl)-1H-1,2,4-triazol-5-yl)benzonitrile (Compound No. 21) 0.016 g of p-toluenesulfonic acid monohydrate Up to 0.15 g of 2,2,2-trifluoro-fluorene'-(2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl)acetamide In a mixed solution of 0.11 g of 2-cyanobenzaldehyde and 5 mL of toluene, followed by heating under reflux by an azeotropic dehydration apparatus for 4 hours. Then, further adding 0.008 g of p-toluenesulfonic acid monohydrate, followed by heating to reflux 1 After 4 hours, water was added to the reaction solution, followed by extraction with ethyl acetate. Then, the organic layer was washed with water and a sodium chloride aqueous solution, and anhydrous sodium sulfate was added to dry. The solvent was distilled off under reduced pressure, and the residue was subjected to a solvent. Column chromatography purification (solvent: n-hexane / ethyl acetate = 1 / 0 to 4 / 1) gave 0.058 g of the desired product oil. Preparation Example 4 1-(2-fluoro-4-methyl - 5-(2,2,2-Trifluoroethylthio)phenyl)-5-( 2·nitrophenyl)-3-(trifluoromethyl)-1H-1,2,4-triazole Preparation of Compound Blend-50-201127291 No. 25, 0.044 g of p-toluenesulfonic acid monohydrate was added to 2,2,2-trifluoro-Ν'-(2-fluoro-) containing 0.4 g 4-methyl-5-(2,2,2-trifluoroethylthio)phenyl)acetamidamine, 〇35 g 2-nitrobyl Of toluene and 10 mL of mixed solution, followed by azeotropic dehydration apparatus was heated to reflux for 2 hours. The reactor taken out from the oil bath, and cooled to room temperature. Then, 0.23 g of triethylamine, followed by reaction for 22 hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. Then, the organic layer was washed with water and an aqueous solution of sodium chloride, and anhydrous sodium sulfate was added to dry. The solvent was evaporated under reduced pressure and the residue was purified mjjjjjjjjjjj Preparation Example 5 2-(1-(2-Fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl)-3-(trifluoromethyl)-1H-1 Preparation of 2,4-triazol-5-yl)aniline (Compound No. 26) 0.050 g of 5% palladium on carbon was added to 1-(2-fluoro-4-methyl-5-(2) containing 0.27 g , 2,2-Trifluoroethylthio)phenyl)-5-(2-nitrophenyl)-3-(trifluoromethyl)-1H-1,2,4-triazole (Compound No. 25) In a mixed solution of 10 mL of methanol, the inside of the reaction system was ventilated with hydrogen, and then reacted at room temperature for 22 hours. After the reaction, water was added to the reaction mixture, followed by filtration. The filtrate obtained was extracted with ethyl acetate. Then, the organic layer was washed with water and a sodium chloride aqueous solution, and anhydrous sodium sulfate was added thereto for drying. The solvent was distilled off under reduced pressure, and the residue was purified mjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjj Preparation Example 6 5-(2-Chlorophenyl)-1-(2-fluoro-4-methyl-5-(2,2,2-dioxaethyl)phenyl)-3-(trifluoro) Preparation of methyl)-1H-1,2,4-triazole (Compound No. 10) 0.002 mL of hydrazine, hydrazine-dimethylformamide was added to contain 0.14 g of 2-chlorobenzoic acid, 2 mL of tetrahydrofuran. And 0.10 mL of a mixture of grass and chlorine. After reacting at room temperature for 1 hour, the reaction mixture was concentrated under reduced pressure to give 2-chlorobenzylidene chloride. In the separation reactor, 0.30 g of 2,2,2-trifluoro-N,-(2-fluoro-4-methyl-5.(2,2,2-trifluoroethylthio)phenyl) was added. Acetamide, 5 mL of I,4-dioxane and 0.075 g of pyridine. To the mixed solution, a previously mixed solution of 2-chlorobenzhydrin chloride and 2 mL of 1,4-dioxane was added dropwise, followed by heating under reflux for 6 hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. Then, the organic layer was washed with water and an aqueous solution of sodium chloride, and anhydrous sodium sulfate was added to dry. The solvent was distilled off under reduced pressure, and the residue was purified by methylene chloride column chromatography (solvent: n-hexane/ethyl acetate = 1/0 to 1/1) to give the desired product as an oil. Preparation Example 7 4-Chloro-2-(1-(2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl)-3-(trifluoromethyl) Preparation of -1H-1,2,4-triazol-5-yl)pyridine (Compound No. 39) 0.002 mL of N,N-dimethylformamide was added to contain 0.15 g of -52-201127291 4 - Chloroquine is a mixture of D-formic acid, 2 mL of tetrahydrofuran and 0_10 mL of grass-brewed chlorine. After reacting at room temperature for 1 hour, the reaction mixture was concentrated under reduced pressure to give 4-chloropyridinium chloride. In the separation reactor, 〇. 30 g of 2,2,2-trifluoro (-Ν'-( 2 -win-4 -methyl-5-( 2,2,2-di-ethanethio) Phenyl)acetamide, 5 mL of 1,4-dioxane and ruthenium 75 g of pyridine. In the mixed solution, the previously prepared 4-chloropyridinium chloride and 3 were added dropwise. a mixed solution of m, 1,4-dioxane, followed by heating under reflux for 6 hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. Then, the organic layer was washed with water and aqueous sodium chloride, and anhydrous sulfuric acid was added. The sodium was dried, and the solvent was evaporated under reduced pressure. Preparation Example 8 2-(1-(5-(1-Chloro-2,2,2-trifluoroethylthio)-2-fluoro-4-methylphenyl)-3-(trifluoromethyl) Preparation of -1H-1,2,4-triazol-5-yl)pyridine (Compound No. 64) 0.18 g of N-chlorosuccinimide was added to 2-( ΙΟ-fluoro-4-) containing 0.30 g Methyl-5-(2,2,2-trifluoroethylthio)phenyl)-3-(trifluoromethyl)-1Η-1,2,4-triazol-5-yl)pyridine (compound) No. 32) and 5 mL of hydrazine, a mixed solution of hydrazine-dimethylformamide, followed by a reaction at room temperature for 16 hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. Then, the organic layer was washed with water and an aqueous solution of sodium chloride, and anhydrous sodium sulfate was added to dry. The solvent was evaporated under reduced pressure, and the residue was purified mjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjjj PREPARATIVE EXAMPLE 9 2-(1-(4-Methyl-3-(2,2,2-trifluoroethylthio)phenyl)-3-(trifluoromethyl)-1H-1,2,4 -Triazol-5-yl)pyridine (Compound No. 131) Preparation (1) 8.40 g of p-toluene hydrochloride, 9.10 g of trifluoroacetaldehyde hemiethyl acetal, 4.33 g of sodium acetate and 100 The mixture of mL ethanol was heated to reflux for 2 hours. The reaction solution was cooled to room temperature, and then water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with water and a sodium chloride aqueous solution, and anhydrous sodium sulfate was added to dry. Then, the solvent was evaporated under reduced pressure to give 1-(p-tolyl)-2-(2,2,2-trifluoroethylidene) oxime. (2) Add 50 mL of N,N-dimethyl group to 1_(p-tolyl)·2-(2,2,2-trifluoroethylene) oxime obtained in (1) Methionamide and 9.4 g of N-bromosuccinimide were reacted for 30 minutes at room temperature. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with water and an aqueous solution of sodium chloride, and anhydrous sodium sulfate was added to dry. Then, the solvent was distilled off under reduced pressure to give 2,2,2-trifluoro-indole-(p-tolyl)ethylhydrazinium bromide. (3) Add 120 mL of chloroform and 60 mL of 28% ammonia solution to 2,2,2-trifluoro-Ν'-(p-tolyl)ethenyl bromide obtained in (2). After that, it was reacted at room temperature for 1.5 hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with water and an aqueous solution of sodium chloride -54-201127291, and anhydrous sodium sulfate was added for drying. Then, 2,2,2-trifluoro-N'-(p-tolyl)acetamide was obtained under reduced pressure. The 1H-NMR data [measured by 1H-nuclear magnetic resonance spectroscopy, 5 system is as follows]. iH-NMR (solvent: (D3C) 2S = 0/400 MHz) δ (8.3 1 ( lH, s ), 6.97 (2H, d), 6.81 ( 2H, d ) , 6.33 ( ), 2.16 ( 3H, s ) ( 4) Add 100 mL of toluene, 6.02 g of 2-pyridyl and 1.94 g of p-toluene to the total amount of (2) 2,2,2-trifluoro-indole-(I-based) acetamidine obtained. The sulfonic acid monohydrate was then refluxed for 1 hour by azeotropic dehydration heat. The reactor was taken out from the oil bath and cooled to room temperature' plus 1 0.3 g of triethylamine, followed by a reaction of 20 hours. Water was added to the solution, after which It was extracted with ethyl acetate. Then the organic layer was washed with water and aqueous solution, and anhydrous sodium sulfate was added to carry out drying. The residue was purified by a solvent column chromatography under reduced pressure solvent (solvent: acid ethyl ester = 1/0) To 9/1), 9.09 g of 2-(b-p-toluene; (trifluoromethyl)-1H-1,2,4-trio- _5-yl)pyrylene (melting point: ) is obtained. 1H-NMR data are as follows. ]H-NMR (solvent: CDC13/4 〇〇MHz) δ (ppm): lH, dd), 7.94 (1H, dd), 7.79 (lH, dt), 7.35-7.30), 7.26 ( 2H,d), 7.21 ( 2H,d), 2.40 ( 3H,s) (5 ) Slowly under ice cooling 'in 17·8 mL of chlorosulfonic acid 4) The obtained 9.09 g of 2-0-(p-tolyl)-3-(trifluoro 1 1 Η -1,2,4-triazol-5-yl)pyrrole was reacted at 1 2 0 °c. The small distillate dissolves this product to shift the ppm): 2 Η, brs - the toluidine formaldehyde device is added and then added to the reaction sodium chloride to distill off 5 alkane / B S) -3-9 2.4. . 8.48 ((1H, m when added (methyl)·. anti-55- 201127291 The solution should be cooled to room temperature, then added to ice water, then extracted with ethyl acetate. The organic layer was washed with water and aqueous sodium chloride Anhydrous sodium sulfate was added to dryness, and then the solvent was distilled off under reduced pressure to give 2-methyl-5-(5-(pyridin-2-yl)-3-(trifluoromethyl)-1H-1,2 , 4 -triazol-1-yl)benzene-1-sulfonyl chloride. (6) The total amount of (5) 2-methyl-5-(5-(pyridin-2-yl)-3-() a mixture of trifluoromethyl)-1H-1,2,4-triazol-1-yl)benzene-1-sulfonyl chloride, 30 mL of acetic acid, 1.58 g of red phosphorus and 0.25 g of iodine at 100 ° C The reaction mixture was cooled to room temperature, and then the solid was filtered off from the reaction mixture. The obtained filtrate was concentrated under reduced pressure and the residue was purified by column chromatography (solvent: n-hexane / ethyl acetate = 7 / 3 to 0/10) 4.82 g of 2-methyl-5-(5-(pyridin-2-yl)-3-(trifluoromethyl)-1H-1,2,4-triazole-1- Phenyl mercaptan (melting point: 111.7T:). (7) Containing 0.20 g of 2-methyl-5·(5-(pyridin-2-yl)-3-(trifluoromethyl)-1H- 1,2,4-triazole-1- a mixture of phenylthiol, 0.12 g of potassium carbonate, 0.07 g of Rongalit and 3 mL of hydrazine, hydrazine-dimethylformamide, 0.19 g of 1,1,1-trifluoro-2 a mixed solution of iodoethane and 1 mL of hydrazine, hydrazine-dimethylformamide, and then reacted at room temperature for 16 hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. Then, the organic layer was water and The aqueous solution of sodium chloride was washed, and anhydrous sodium sulfate was added to dry. The solvent was evaporated under reduced pressure, and the residue was purified by column chromatography (solvent: n-hexane/ethyl acetate = 1/0 to 9/1) 0.18 g of a solid of the desired product are obtained. A typical example of a compound of the above formula (I) is shown in Table 1. These compounds can be based on the aforementioned preparation examples or by the various methods described above for the manufacture of the compounds of the invention. To prepare. In Table 1, the number indicates the compound number, M e : methyl; Et: ethyl; n-Pr: n-propyl; i-pr: isopropyl; c-Pr: cyclopropyl; Bu: tert-butyl; i-Bu: isobutyl; Ph: phenyl; and Py: pyridyl 'the physical temperature is the melting point. In addition, some of the compounds of the former formula (Ϊ) Words, iH-NMR data [NMR spectra measured by ιΗ_ 'δ chemical shift Department] series are shown in Table 2. -57 · 201127291 R1

No. R1 R2 R3 R4 R5 n Physical Properties 1 cf3 Ph F Me CH2CF3 〇93.6°C 2 cf3 2-Me-Ph F Me CH2CF3 〇Oil 3 cf3 3-Me-Ph F Me CH2CF3 〇76.3°C 4 cf3 4-Me -Ph F Me CH2CF3 〇99.2°C 5 cf3 2-Et-Ph F Me CH2CF3 Emu Oil 6 cf3 2~CF3*Ph F Me CH2CF3 Emu Oil 7 cf3 2-F-Ph F Me CH2CF3 Emu Oil 8 cf3 3-F -Ph F Me CH2CF3 〇9 cf3 4-F-Ph F Me CH2CF3 〇10 cf3 2-CI-Ph F Me CH2CF3 〇11 cf3 2-CI-Ph F Me CH2CF3 1 12 cf3 3-CI-Ph F Me CH2CF3 〇115.4°C 13 cf3 4-CI-Ph F Me CH2CF3 〇120.5°C 14 cf3 2-Br-Ph F Me CH2CF3 〇 oil 15 cf3 2-l-Ph F Me CH2CF3 〇 oil 16 cf3 2-OMe-Ph F Me CH2CF3 Emu Oil 17 cf3 3-OMe-Ph F Me CH2CF3 〇103.8°C 18 cf3 4-OMe-Ph F Me CH2CF3 〇99.3°C 19 cf3 2-OCF3_Ph F Me CH2CF3 Emu Oil 20 cf3 2-SMe-Ph F Me CH2CF3 Emu Oil 21 cf3 2-CN-Ph F Me CH2CF3 Emu Oil 22 cf3 2-CN-Ph F. Me CH2CF3 1 23 cf3 3-CN-Ph F Me CH2CF3 Emu Oil 24 cf3 4-CN-Ph F Me CH2CF3 Emu oil 25 cf3 2*N〇2~Ph F Me CH2CF3 Emu oil-58- 201127291 Table 1 (continued) No. R1 R2 R3 R4 R5 n Nature 26 cf3 2-NH2-Ph F Me CH2CF3 0 90.0°C 27 cf3 2,3-CI2-Ph F Me ch2cf3 0 Oil 28 cf3 2,4-CI2-Ph F Me CH2CF3 0 Oil 29 cf3 2,5-CI2 -Ph F Me CH2CF3 0 Oil 30 cf3 2,6-CI2-Ph F Me CH2CF3 0 Oil 31 cf3 2,6-F2-Ph F Me CH2CF3 0 Oil 32 cf3 2-Py F Me CH2CF3 0 91.0°C 33 cf3 2 -Pv F Me CH2CF3 1 110-120°C 34 cf3 2-Pv F Me CH2CF3 2 120-130°C 35 cf3 3-Me-2-Py F Me CH2CF3 0 94.9°C 36 cf3 6-Me-2-Py F Me CH2CF3 0 124.4°C 37 cf3 3-CI-2-PV F Me CH2CF3 0 106.9°C 38 cf3 3-CI-2-PV F Me CH2CF3 1 39 cf3 4-CI-2-PV F Me CH2CF3 0 100.9 °C 40 cf3 5-CI-2-PV F Me ch2cf3 0 41 cf3 6-CI-2-PV F Me CH2CF3 0 42 cf3 3-Br-2-Py F Me CH2CF3 0 43 cf3 3-Br-2-Py F Me CH2CF3 1 44 cf3 5-Br-2-Py F Me ch2cf3 0 126-128°C 45 cf3 6-Br-2-Py F Me ch2cf3 0 120.7°C 46 cf3 4-CF3*2-Py F Me ch2cf3 0 81.4°C 47 cf3 5-CF3*2-Pv F Me CH2CF3 0 106.8°C 48 cf3 3~CI-5*CF3-2-Py F Me CH2CF3 0 Oil 49 cf3 3-CN-2-PV F Me ch2cf3 0 50 cf3 3*ON-2-Py F Me CH2CF3 1 51 cf3 3-Py F Me ch2cf3 0 109.9°C 52 cf3 2-CI-3-Pv F Me CH2CF3 0 Oil 53 cf3 4-CI-3-PV F Me ch2cf3 0 Oil 54 cf3 4-Py F Me CH2CF3 0 113.7°C 55 cf3 3-CI-4-Py F Me CH2CF3 0 Oil 56 cf3 2-CI -Ph F Me cf3 0 57 cf3 2-C!-Ph F Me ch2ch2cf3 0 58 cf3 2-CI-Ph F Me ch2cn 0 59 cf3 2-CI-Ph F Me CH2(c-Pr) 0 60 cf3 2-CN -Ph F Me cf3 0 61 cf3 2-CN-Ph F Me ch2ch2cf3 0 -59- 201127291 Table 1 (Revocation number R1 R2 R3 R4 R5 n Physical properties 62 cf3 2-CN-Ph F Me CH2CN 0 63 cf3 2-CN -Ph F Me CH2(c-Pr) 0 64 cf3 2-Py F Me CHCICF3 0 101.9°C 65 cf3 2-Py F Me cf3 0 66 cf3 2-Pv F Me CH2CH2CF3 0 67 cf3 2-Py F Me CH2CN 0 68 cf3 2-Pv F Me CH2(c-Pr) 0 69 cf3 2-Pv F Me Me 0 70 cf3 2-Pv F Me Et 0 71 cf3 2-Py F Me n-Pr 0 72 cf3 2-Pv F Me i-Pr 0 73 cf3 2-Pv F Me CH2CH=CH2 0 74 cf3 3-CI-2-PV F Me cf3 0 75 cf3 3-CI-2-PV F Me ch2ch2cf3 0 76 cf3 3-01-2-Py F Me ch2cn 0 77 cf3 3-CI-2-PV F Me CH2(c-Pr) 0 78 Me 2-Py F Me CH2CF3 0 79 Et 2-Py F Me ch2cf3 0 80 n-Pr 2-Py F Me CH2CF3 0 81 i-Pr 2-CI-Ph F Me CH2CF3 0 82 i-Pr 2-CN-Ph F Me CH2CF3 0 83 i-Pr 2-Pv F Me ch2cf3 0 84 i-Pr 3-CI-2-PV F Me ch2cf3 0 85 t-Bu 2*CI-Ph F Me ch2cf3 0 86 t-Bu 2-CN-Ph F Me CH2CF3 0 87 t-Bu 2-Pv F Me CH2CF3 0 Oil 88 t-Bu 3-CI-2-Py F Me ch2cf3 0 89 i-Bu 2-CI-Ph F Me CH2CF3 0 90 i-Bu 2-CN -Ph F Me CH2CF3 0 91 j-Bu 2-Pv F Me CH2CF3 0 92 i-Bu 3-CI-2-Py F Me CH2CF3 0 93 cf3 2-CI-Ph Me Me CH2CF3 0 Oil 94 cf3 2-CI- Ph Me CN CH2CF3 0 95 cf3 2-CI-Ph Me Cl CH2CF3 0 96 cf3 2-CI-Ph Me Br ch2cf3 0 97 cf3 2-CI-Ph Me I ch2cf3 0 -60- 201127291 Table 1 (continued) No. R1 R2 R3 R4 R5 n Physical Properties 98 cf3 2-CI-Ph CN Me CH2CF3 0 99 cf3 2-CI-Ph CN Cl CH2CF3 0 100 cf3 2-CI-Ph CN Br ch2cf3 0 101 cf3 2-CI-Ph F CN ch2cf3 0 102 cf3 2-CI-Ph F Cl CH2CF3 0 103 cf3 2-CI-Ph F Br CH2CF3 0 104 cf3 2-CI-Ph Cl Me CH2CF3 0 Oil 105 cf3 2-CI-Ph Cl CN CH2CF3 0 106 cf3 2-CI -Ph Cl Cl ch2cf3 0 107 cf3 2-CI-Ph Cl Br CH2CF3 0 108 cf3 2-CI-Ph Br Me ch2cf3 0 109 cf3 2-CI-Ph Br CN CH2CF3 0 110 cf3 2-CI-Ph Br Cl CH2CF3 0 111 cf3 2-CI-Ph Br Br ch 2cf3 0 112 cf3 2-CN-Ph Me Me CH2CF3 0 100.9°C 113 cf3 2-CN-Ph Me CN ch2cf3 0 114 cf3 2-CN-Ph Me Cl ch2cf3 0 115 cf3 2-CN-Ph Me Br ch2cf3 0 116 Cf3 2-CN-Ph Me I ch2cf3 0 117 cf3 2-CN-Ph CN Me ch2cf3 0 118 cf3 2-CN-Ph CN Cl ch2cf3 0 119 cf3 2-CN-Ph CN Br ch2cf3 0 120 cf3 2-CN-Ph F CN ch2cf3 0 121 cf3 2-CN-Ph F Cl CH2CF3 0 122 cf3 2-CN-Ph F Br ch2cf3 0 123 cf3 2-CN-Ph Cl Me ch2cf3 0 Oil 124 cf3 2-CN-Ph Cl CN CH2CF3 0 125 Cf3 2-CN-Ph Cl Cl CH2CF3 0 126 cf3 2-CN-Ph Cl Br CH2CF3 0 127 cf3 2-CN-Ph Br Me CH2CF3 0 128 cf3 2-CN-Ph Br CN CH2CF3 0 129 cf3 2-CN-Ph Br Cl CH2CF3 0 130 cf3 2-CN-Ph Br Br CH2CF3 0 131 cf3 2-Py H Me ch2cf3 0 85.3°C 132 cf3 2-Pv Me Me CH2CF3 0 84.9°C 133 cf3 2-Pv Me CN CH2CF3 0 :3⁄4 -61 - 201127291 No. R1 R2 R3 R4 R5 n Physical Properties 134 cf3 2-Pv Me Cl CH2CF3 0 89.8°C 135 cf3 2-Py Me Br ch2cf3 0 136 cf3 2-Py Me I ch2cf3 0 137 cf3 2-Pv CN Me ch2cf3 0 138 cf3 2-Pv CN Cl ch2cf3 0 139 cf3 2-Pv CN Br ch2cf3 0 140 Cf3 2-Pv F CN CH2CF3 0 120-130°C 141 cf3 2-Pv F Cl CH2CF3 0 142 cf3 2-Pv F Br ch2cf3 0 143 cf3 2-Pv Cl Me ch2cf3 0 144 cf3 2-Pv Cl CN ch2cf3 0 145 Cf3 2-Pv Cl Cl ch2cf3 0 146 cf3 2-Py Cl Br ch2cf3 0 147 cf3 2-Pv Br Me CH2CF3 0 148 CF3 2-Pv Br CN CH2CF3 0 149 cf3 2-Pv Br Cl CH2CF3 0 150 cf3 2-Pv Br Br CH2CF3 0 151 cf3 3-CI-2-Py Me Me CH2CF3 0 152 cf3 3-CI-2-Py Me CN CH2CF3 0 153 cf3 3-CI-2-PV Me Cl CH2CF3 0 154 cf3 3-CI-2- Py Me Br CH2CF3 0 155 cf3 3-CI-2-PV Me I ch2cf3 0 156 cf3 3-CI-2-PV CN Me CH2CF3 0 157 cf3 3-CI-2-Py CN Cl CH2CF3 0 158 cf3 3-CI- 2-Py CN Br CH2CF3 0 159 cf3 3-CI-2-Py F CN CH2CF3 0 160 cf3 3-CI-2-Py F Cl CH2CF3 0 161 cf3 3-CI-2-Py F Br ch2cf3 0 162 cf3 3* CI-2-Py Cl Me ch2cf3 0 163 cf3 3-CI-2-Py Cl CN CH2CF3 0 164 cf3 3-CI-2-Py Cl Cl CH2CF3 0 165 cf3 3-CI-2-Py Cl Br ch2cf3 0 166 cf3 3-CI-2-PV Br Me CH2CF3 0 167 cf3 3-CI-2-Py Br CN ch2cf3 0 168 cf3 3-CI-2-Py Br Cl CH2CF3 0 169 cf3 3-CI-2-Py Br Br ch2cf3 0 -62- 20 1127291 Table 1 (continued) No. R1 R2 R3 R4 R5 Gate Physical Properties 170 cf3 3-OMe-2-Py F Me CH2CF3 0 171 cf3 2-OEt-Ph F Me CH2CF3 0 Oil 172 cf3 3,4-CI2-Ph F Me CH2CF3 0 Oil 173 cf3 3,5-CI2-Ph F Me CH2CF3 0 Oil 174 cf3 2,3,4-CI3-Ph F Me CH2CF3 0 175 cf3 2,3,5-CI3-Ph F Me ch2cf3 0 Oil 176 Cf3 2,3,6-CI3-Ph F Me CH2CF3 0 Oil 177 cf3 2,4,5-CI3-Ph F Me CH2CF3 0 Oil 178 cf3 2,4,6-CI3-Ph F Me CH2CF3 0 179 cf3 5- CI-3-PV F Me CH2CF3 0 Oil 180 cf3 6-CI-3-PV F Me ch2cf3 0 Oil 181 cf3 2-CI-4-PV F Me ch2cf3 0 Oil 182 cf3 2-OMe-Ph Me Me ch2cf3 0 107.3 °C 183 cf3 2-OMe-Ph Me CN CH2CF3 0 184 cf3 2-OMe-Ph Me Cl ch2cf3 0 185 cf3 2-OMe-Ph Me Br ch2cf3 0 186 cf3 2-OMe-Ph Me I ch2cf3 0 187 cf3 2- OMe-Ph CN Me ch2cf3 0 188 cf3 2-OMe-Ph CN Cl ch2cf3 0 189 cf3 2-OMe-Ph CN Br CH2CF3 0 190 cf3 2-OMe-Ph F CN CH2CF3 0 191 cf3 2-OMe-Ph F Cl ch2cf3 0 192 cf3 2-OMe-Ph F Br ch2cf3 0 193 cf3 2-OMe-Ph Cl Me CH2CF3 0 81.0°C 194 cf3 2-OMe-Ph Cl CN ch2cf3 0 195 cf3 2-OMe-Ph Cl Cl CH2CF3 0 1 96 cf3 2-OMe-Ph Cl Br CH2CF3 0 197 cf3 2-OMe-Ph Br Me CH2CF3 0 198 cf3 2-OMe-Ph Br CN ch2cf3 0 199 cf3 2-OMe-Ph Br Cl ch2cf3 0 200 cf3 2-OMe- Ph Br Br CH2CF3 0 201 cf3 2,4-CI2-Ph Me Me CH2CF3 0 202 cf3 2,4-CI2-Ph Me CN CH2CF3 0 203 cf3 2,4-CI2-Ph Me Cl ch2cf3 0 204 cf3 2,4- CI2-Ph Me Br ch2cf3 0 205 cf3 2,4-CI2-Ph Me I ch2cf3 0 -63- 201127291 Table 1 (continued) No. R1 R2 R3 R4 R5 n Physical Properties 206 cf3 2,4-CI2-Ph CN Me CH2CF3 0 207 cf3 2,4-CI2-Ph CN Cl CH2CF3 0 208 cf3 2,4-CI2-Ph CN Br CH2CF3 0 209 cf3 2,4-CI2-Ph F CN CH2CF3 0 210 CF3 2,4-Clz-Ph F Cl CH2CF3 0 211 cf3 2,4-Cl2~Ph F Br ch2cf3 0 212 CF3 2,4-CI2-Ph Cl Me CH2CF3 0 213 cf3 2,4-CI2-Ph Cl CN CH2CF3 0 214 cf3 2,4-Cl2* Ph Cl Cl CH2CF3 0 215 cf3 2,4-CI2-Ph Cl Br CH2CF3 0 216 cf3 2,4-CI2-Ph Br Me CH2CF3 0 217 cf3 2,4-CI2-Ph Br CN CH2CF3 0 218 CF3 2,4- CI2-Ph Br Cl ch2cf3 0 219 cf3 2,4-Cl2~Ph Br Br CH2CF3 0 220 cf3 2,5-CI2-Ph Me Me CH2CF3 0 221 cf3 2,5-CI2-Ph Me CN ch2cf3 0 222 cf3 2, 5-Cls- Ph Me Cl CH2CF3 0 223 cf3 2,5-CI2-Ph Me Br CH2CF3 0 224 cf3 2,5-CI2-Ph Me I CH2CF3 0 225 cf3 2,5-CI2-Ph CN Me CH2CF3 0 226 cf3 2,5- CI2-Ph CN Cl CH2CF3 0 227 cf3 2,5-CI2-Ph CN Br ch2cf3 0 228 cf3 2,5-CI2-Ph F CN CH2CF3 0 229 cf3 2,5-CI2-Ph F Cl ch2cf3 0 230 cf3 2, 5-CI2-Ph F Br ch2cf3 0 231 cf3 2,5-CI2-Ph Cl Me CH2CF3 0 232 CF3 2,5-CI2-Ph Cl CN CH2CF3 0 233 cf3 2,5-CI2-Ph Cl Cl chcf3 0 234 cf3 2,5-CI2-Ph Cl Br ch2cf3 0 235 cf3 2,5-CI2-Ph Br Me CH2CF3 0 236 cf3 2,5-CI2-Ph Br CN ch2cf3 0 237 cf3 2,5-CI2-Ph Br Cl ch2cf3 0 238 cf3 2,5-CI2*Ph Br Br CH2CF3 0 239 cf3 4~CI~3~Py Me Me ch2cf3 . 0 240 cf3 4-CI-3-PV Me CN CH2CF3 0 -64- 201127291 Table 1 (continued) No. R1 R2 R3 R4 R5 n Physical Properties 241 cf3 4-CI-3-PV Me Cl CH2CF3 0 242 cf3 4-CI-3-PV Me Br CH2CF3 0 243 cf3 4-CI*3-Py Me I ch2cf3 0 244 cf3 4 -CI-3-PV CN Me CH2CF3 0 245 cf3 4-CI-3-PV CN Cl CH2CF3 0 246 cf3 4-CI-3-PV CN Br ch2cf3 0 247 cf3 4-CI-3-Pv F CN ch2cf3 0 248 Cf3 4-CI-3-PV F Cl ch2cf3 0 249 cf3 4-CI-3-PV F Br CH2CF3 0 250 cf3 4-CI-3-PV Cl Me ch2cf3 0 251 cf3 4-CI-3-PV Cl CN ch2cf3 0 252 cf3 4-CI~3~Pv Cl Cl CH2CF3 0 253 cf3 4-CI-3*Py Cl Br CH2CF3 0 254 cf3 4-CI-3-PV Br Me CH2CF3 0 255 cf3 4-GI-3-Py Br CN CH2CF3 0 256 cf3 4~OI-3- Py Br Cl CH2CF3 0 257 cf3 4-CI-3-PV Br Br CH2CF3 0 258 cf3 3-CI-4-PV Me Me ch2cf3 0 259 cf3 3~CI-4-Py Me CN CH2CF3 0 260 cf3 3-CI- 4-PV Me Cl CH2CF3 0 261 cf3 3-CI-4-PV Me Br ch2cf3 0 262 cf3 3-CI-4-Pv Me I ch2cf3 0 263 cf3 3-CI-4-PV CN Me CH2CF3 0 264 cf3 3- CI-4-PV CN Cl CH2CF3 0 265 cf3 3-CI-4-PV CN Br CH2CF3 0 266 cf3 3-CI-4-PV F CN ch2cf3 0 267 cf3 3-CI-4-PV F Cl CH2CF3 0 268 cf3 3-CI-4-PV F Br CH2CF3 0 269 cf3 3-CI-4-PV Cl Me CH2CF3 0 270 cf3 3-CI-4-Pv Cl CN CH2CF3 0 271 cf3 3-CI-4-PV Cl Cl CH2CF3 0 272 cf3 3-CI-4-Pv Cl Br CH2CF3 0 273 cf3 3*GI~4-Py Br Me CH2CF3 0 274 cf3 3-CI-4-PV Br CN CH2CF3 0 275 cf3 3-CI-4-Py Br Cl CH2CF3 0 -65- 201127291 Table 1 (continued) No. R1 R2 R3 R4 R5 n Physical 276 cf3 3-CI-4-Pv Br Br CH2CF3 0 277 cf3 4-CI*2-Py Me Me CH2CF3 0 278 cf3 4-Cl_2-Py Me CN ch2cf3 0 279 cf3 4-CI-2-Py Me Cl CH2CF3 0 280 cf3 4-CI-2-PV Me Br CH2CF3 0 281 cf3 4eCI~2_Py Me I CH2CF3 0 282 cf3 4-CI-2-Py CN Me CH2CF3 0 283 cf3 4-CI-2-Pv CN Cl ch2cf3 0 284 Cf3 4-CI-2_Py CN Br ch2cf3 0 285 cf3 4-CI-2-PV F CN ch2cf3 0 286 cf3 4-CI-2-PV F Cl CH2CF3 0 287 cf3 4-CI-2-Py F Br CH2CF3 0 288 Cf3 4-CI-2-PV Cl Me CH2CF3 0 289 cf3 4-CI-2-PV Cl CN CH2CF3 0 290 cf3 4-CI-2-Py Cl Cl CH2CF3 0 291 cf3 4-CI-2-PY Cl Br CH2CF3 0 292 cf3 4-CI*2-Py Br Me ch2cf3 0 293 cf3 4-CI-2-Pv Br CN CH2CF3 0 294 cf3 4-CI~2-Py Br Cl CH2CF3 0 295 cf3 4-CI~2-Py Br Br ch2cf3 0 296 cf3 5-Ct-2-Py Me Me ch2cf3 0 297 cf3 5-CI-2-Py Me CN ch2cf3 0 298 cf3 5-CI-2-PV Me Cl ch2cf3 0 299 cf3 5-CI-2- PV Me Br CH2CF3 0 300 cf3 5-CI-2-PV Me I CH2CF3 0 301 CF3 5.CI-2-PV CN Me CH2CF3 0 302 cf3 5-CI-2-PV CN Cl CH2CF3 0 303 cf3 5-CI- 2-PV CN Br CH2CF3 0 304 cf3 5-CI-2-Py F CN CH2CF3 0 305 cf3 5-CI-2-Py F Cl CH2CF3 0 306 cf3 5-CI-2-Py F Br CH2CF3 0 307 cf3 5-CI-2-PV Cl Me CH2CF3 0 308 cf3 5OI*2-Py Cl CN ch2cf3 0 309 cf3 5-CI-2-PV Cl Cl CH2CF3 0 310 cf3 5-CI-2-Py Cl Br ch2cf3 0 -66 - 201127291 Table 1 (continued) No. R1 R2 R3 R4 R5 n Physical Properties 311 CF2CF3 2-Pv H Me CH2CF3 0 68.1 °C 312 CH2CF3 2-Pv H Me CH2CF3 0 62.7°C 313 cf3 2-Py H Et CH2CF3 0 83.7°C 314 cf3 2-PV H Cl ch2cf3 0 123.7°C 315 cf3 2- Pv H Me Me 0 83.5°C 316 cf3 2-Pv H Me Et 0 101.2°C 317 cf3 2-Pv H Me n-Pr 0 56.9°C 318 cf3 2-Pv H Me i-Pr 0 Oil 319 cf3 2- Pv H Me n-Bu 0 39.7°C 320 cf3 2-Py H Me i-Bu 0 67.4°C 321 cf3 2-Pv H Me i-Bu 1 127.3°C 322 cf3 2-Pv H Me CH2(c-Pr 0 77.0°C 323 cf3 2-Pv H Me CH2CH2F 0 78.6°C 324 cf3 2-Pv H Me ch2ch2ci 0 95.3°C 325 cf3 2-Pv H Me CH2CH2Br 0 101.8°C 326 cf3 2-Pv H Me CH2CF3 1 136.5°C 327 cf3 2-Pv H Me cf2cf2h 0 58.0°C 328 cf3 2-Pv H Me ch2ch2cf3 0 82.0°C 329 cf3 2-Pv H Me CH2CH2CF3 1 124.4°C 330 cf3 Ph H Me CH2CF3 0 68.7°C 331 cf3 Ph H Me CH2CF3 1 152.9°C 332 cf3 2-CI-Ph H Me CH2CF3 0 Oil 333 cf3 2-CI-Ph H Me CH2CF3 1 Oil 334 cf3 2-CN-Ph H Me CH2CF3 0 Oil 335 cf3 2-CN-Ph H Me CH2CF3 1 Oil 336 cf3 2-OMe-Ph H Me ch2cf3 0 Oil 337 cf3 2-OMe-Ph H Me CH2CF3 1 Oil 338 cf3 2-CI-Ph Cl Me CH2CF3 1 Oil 339 cf3 2-OMe-Ph Cl Me CH2CF3 1 Oil 340 cf3 2-CN-Ph Cl Me CH2CF3 1 Oil 341 cf3 2-Pv Me Me ch2cn 0 126.5°C 342 cf3 2-CI-Ph Me Me CH2CF3 1 Oil 343 cf3 2- OMe-Ph Me Me CH2CF3 1 Oil 344 cf3 2-CN-Ph Me Me ch2cf3 1 Oil 345 cf3 2-Py Cl Me ch2cf3 1 131.8°C 346 cf3 2-Pv H Me CH2CH2CCI3 0 Oil-67- 201127291 Table 2 No. 1H -NMR δρριτι (Solvent : CDCI;j/400MHz ) 2 7.46(1 H,d), 7.34-7.24(2H,m), 7.15-7.02(2H,m), 6.99(1 H,d), 3.15(2H ,q), 2.4 6(3H,s), 2.22(3H,s) 5 7.45(1H,d), 7.40-7.34(1 H,m), 7.29(1H,d), 7.15-7.06(2H,m ), 7.01(1H,d), 3.1 5(2H,q), 2.57(2H,q), 2.45(3H,s), 1.11(3H,t) 6 7.73(1 H,d), 7.64-7.54( 2H,m), 7.46-7.39(2H,m), 7.00(1 H,d), 3.19(2H,q), 2.4 4(3H,s) 7 7.64-7.58(1 H,m), 7.54(1H, d), 7.50-7.43 (1 H, m), 7.28-7.22 (1 H, m), 7.05-6.98 (2H, m), 3.23 (2H, q), 2.49 (3H, s) 10 7.51- 7.46(2H,m), 7.44-7.39(1 H,m), 7.38-7.32(2H,m), 7.01 (1H,d), 3.18(2H,q ),2.46(3H,s) 14 7.54(1 H,dd), 7.49(1 H,d), 7.45(1 H,dd), 7.40-7.30(2H,m), 7.01 (1H,d), 3.18(2 H,q), 2.45(3H,s 15 7.83(1H,d), 7.54(1H,d), 7.42-7.34(2H,m), 7.18-7.12(1H,m), 7.01(1H,d), 3.2 0(2H,q), 2.45 (3H, s) 16 7.57(1 H,dd), 7.45-7.39(1 H,m), 7.34(1 H,d), 7.09-7.02(2H,m), 6.77(1 H,d), 3 06(2H,q), 3.43(3H,s), 2.46(3H,s) 19 7.66(1 H,dd), 7.57-7.50(1 H,m), 7.46(1 H,d), 7.43- 7.38(1 H,m), 7.24-7.18(1 H, m), 7.03(1 H,d), 3.19(2H,q), 2.48(3H,s) 20 7.47(1H,d), 7.43-7.38 (1 H,m), 7.30(1H,d), 7.25(1H,d), 7.21-7.15(1 H,m), 7.0 0(1 H,d), 3.14(2H,q), 2.44(3H ,s), 2.30(3H,s) 21 7.73-7.65(3H,m), 7.62-7.57(2H,m), 6.97(1 Hd), 3.36(2H,q), 2.48(3H,s) 23 7.84 (1 H,dd), 7.76-7.67(2H,m), 7.50(1 H,dd), 7.23(1 H,d), 3.35(2H,q), 2.56(3 H,s) 24 7.69-7.62 (5H,m), 7.11(1H,d), 3.36(2H,q), 2.56(3H,s) 25 8.06(1 H,dd), 7.77-7.72(1 H,m), 7.68(1 H , dd), 7.67-7.63 (1 H, m), 7.52 (1 H, d), 6.95 (1 H, d), 3.29 (2H, q), 2.44 (3H, s) 26 7.62 (1H, d) , 7.26-7.23(1 H,m), 7.18-7.02(2H,m), 6.82(1H,d), 6.68-6.60(1 H,m ), 3.26(2H,q), 2.51 (3H,s) 27 7.57(1 H,dd), 7.51 (1H,d), 7.39(1 H,dd), 7.30(1 H,d), 7.02(1 H,d), 3.23(2H,q), 2.47(3H , s) 28 7.54(1 H,d), 7.42(1 H,d), 7.38(1 H,d), 7.33(1 H,dd), 7.02(1 H,d), 3.25(2H,q) , 2 .48(3H,s) 29 7.55-7.52(2H,m), 7.39(1 H,dd), 7.28(1 H(d), 7.03(1 H,d), 3.24(2H,q), 2.48(3 H,s) 30 7.50(1 H,d), 7.36-7.34(3H,m), 7.05(1 H,d), 3.19(2H,q), 2.45(3H,s) 31 7.57(1 H,d), 7.49-7.40(1 H,m), 7.03(1 H,d), 6.98-6.91 (2H,m), 3.24(2H,q), 2.4 8(3H,s) -68- 201127291 Table 2 (continued) No. 1H-NMR δρρηι (Solvent : CDCI3MOOMHZ ) 32 8.34-8.31 (1H, m), 8.20 (1 H, dd), 7.85-7.80 (1 Η, m), 7.68 (1 H, d) , 7.34-7.29(1 Η ,m), 7.05(1 H,d), 3.36(2H,q), 2.55(3H,s) 34 8.30-8.26(2H,m), 8.22(1 H,d), 7.87-7.81(1H,m), 7.34-7.30(1 H,m), 7.21 (1H,d),3.97(2H,q), 2.79(3H,s) 39 8.27(1 H,d), 8.21 ( 1H,d), 7.67(1 H,d), 7.32(1 H,dd), 7.05(1 H,d), 3.36(2H,q) , 2 _55(3H,s) 48 8.62(1 H,d), 8.07(1 H,d), 7.65(1 H,d), 7.01 (1H,d), 3.32(2H,q), 2.50(3H , s) 52 8.50(1 H,dd), 7.91(1H,dd), 7.60(1 H,d), 7.37(1 H,dd), 7.00(1 H,d), 3.28(2H,q) , 2.47(3H,s) 53 8.65(1 H,s), 8.60(1 H,d), 7.59(1 H,d), 7.38(1 H,d), 7.02(1 H,d), 3.27(2H , q), 2. 48(3H, s) 55 8.64(1 H,s), 8.61 (1H,d), 7.61 (1H,d), 7.46(1 H,d), 7.02(1 H,d) , 3.29(2H,q), 2. 49(3H,s) 64 8.34-8.31 (1H,m), 8.23(1H,dd), 7.86-7.80(2H,m), 7.34-7.29(1 H,m ), 7.13(1H, d), 5.19(1 H,q), 2.61(3H,s) 87 8.35(1 H,dd), 8.22(1 H,d), 7.80(1 H,m), 7.69( 1 H,d), 7.27(1 H,m), 7.02(1 H,d), 3.36(2H,q), 2.52(3H,s), 1.48(9H,s) 93 7.45-7.32(4H,m ), 7.16(1H,s), 7.12(1H,s), 3.04(2H,q), 2.41(3H,s), 2.19(3H, s) 104 7.46-7.37(4H,m), 7.33-7.25( (2H, m) ), 3.47(2H,q), 2.4 6(3H,s) 171 7.57(1 H,dd), 7.56(1 H,ddd), 7.29(1 H,d), 7.07-7.04(2H,m), 6.76(1 H,d), 3.70( 2H,q), 2.99(2H,q), 2.46(3H,s), 1.09(3H,t) 172 7.75-7.21 (4H,m), 7.14(1 H, d), 3.37 (2H,q), 2.58(3H,s) 173 7.70(1 H,d), 7.51-7.39(3H,m), 7.16(1 H,d), 3.36(2H,q), 2.58(3H,s ) 175 7.59(1 H,d), 7.55(1 H,d), 7.43(1 H,d), 7.05(1 H,d), 3.27(2H,q), 2.49(3H,s) 176 7.53- 7.50(2H,m), 7.29(1 H,d), 7.07(1 H,d), 3.22(2H,q), 2.47(3H,s) 177 7.67(1 H,s), 7.57(1 H, d), 7.47(1 H,s), 7.04(1 H,d), 3.28(2H,q), 2.49(3H,s) 179 8.67(1 H,d), 8.45(1 H,d), 8.20 (1 H,dd), 7.72(1 H,d), 7.15(1 H,d), 3.38(2H,q), 2 ,57(3H,s) 180 8.40(1 H,d), 7.91(1H ,dd), 7.69(1 H,d), 7.39(1 H,d), 7.12(1 H,d), 3.36(2H,q), 2 .55(3H,s) 181 8.40(1H,d) , 7.71(1H,d), 7.57(1H,s), 7.21-7.14(2H,m), 3.38(2H,q), 2.57(3H, s) 318 8.53(1 H,d), 7.97(1 H , d), 7.87(1 H,t), 7.40(1 H,m), 7.30(1 H,d), 7.26(1 H,d), 7. 16(1H,dd), 3.27(1 H. Heptet), 2.41 (3H, s), 1.24(6H,d) -69- 201127291 Table 2瀬) No. 1H-NMR δρρΓη (Solvent : CDCIaMOOMHz ) 332 7.55(1 H,dd), 7.54-7.38(3H,m ), 7.27-7.23(3H,m), 3.12(2H,q), 2.43(3H,s) 333 7.81(1H,d), 7.62(1H,dd), 7.53-7.32(4H,m), 7.28( 1H,d), 3.25-3.17(2H,m), 2. 40(3H,s) 334 7.76-7.70(2H,m), 7.66-7. 61 (2H,m), 7.30-7.25(2H,m), 7.21(1H,dd), 3.21 (2H, q), 2.46(3H,s) 335 7.80.7.64(5H,m), 7.54(1 H , dd), 7.31(1 H,dd), 3.38-3.20(2H,m), 2.42(3H,s) 336 7.59(1 H,dd), 7.48(1 H,t), 7.26-7.24(3H, m), 7.11(1H,t), 6.82(1 H,d), 3.36(3H, s), 3.07(2H,q), 2.43(3H,s) 337 7.89(1 H,d), 7.57-7.45 (3H,m), 7.29(1 H,d), 7.09(1 H,t), 6.84(1 H,d), 3.44(3H,s ),3.31-3.14(2H,m), 2.40(3H, s) 338 8.01 (1H,S), 7.50(1 H,d), 7.43-7.31 (4H,m), 3.30(2H,q), 2.40(3H,s) 339 7.96(1 H,s), 7.56 (1 H,dd), 7.46-7.39(2H,m), 7.04(1 H,t), 6.77(1 H,d), 3.54(3H, s), 3.39-3.17(2H,m), 2.40( 3H, s) 340 8.26 (1 H, s), 7.74 (1 H, d), 7.66-7.53 (3H, m), 7.36 (1 H, s), 3.61-3.43 (2H, m), 2.4 4 ( 3H, s) 342 7.59-7.53(2H,m), 7.44-7.33(3H,m), 7.22(1H,s), 3.10(2H,q), 2.36(3H,s), 2.3 0(3H,s ) 343 7.64(1 H,s), 7.54(1 H,d), 7.44-7.38(1 H,m), 7.20(1 H,s), 7.05(1 H,t), 6.75(1 H,d ), 3.47 (3H, s), 3.24-3.00 (2H, m), 2.37 (3H, s), 2.24 (3H, s) 344 7.62-7.58 (5H, m), 7.27 (1 H, s), 3.27 -3.18(2H,m), 2.39(3H,s), 2.29(3H,s) 346 8.53(1 H,d), 8.06(1 H,d), 7.90(1 H,t), 7.42(1 H,t), 7.33(1 H,d), 7.26(1 H,d), 7.1 6(1H,dd), 3.21-3.17(2H,m), 2.92-2.88(2H,m), 2.42 (3H, s) Now, a test case will be described. Test Example 1 Test of adult (Tetranychusurticae) adult The insecticidal solution was prepared, and the concentration of the compound of the present invention was adjusted to 2 〇〇ppm. The bean with only one initial leaf was transferred to a pot (diameter: 8 cm' height: 7 cm), and 20 adult spider mites were released on the pot. Together with the kidney bean leaves, they were immersed in the aforementioned insecticidal solution, dried in the air, and then left in a thermostat bath with illumination at 25 °C. On the second or third day after treatment, the number of dead adults was counted, and adult mortality was calculated by the following formula. Adults that fall from the leaves and dying are included in the number of deaths. For the aforementioned compound numbers 1, 2, 6-70-201127291, 7, 10, 14-16, 20, 21, 25, 26, 28, 29, 32, 33, 35, 37, 39, 44, 46, 5 1 - 55, 87, 131, 132, 143, 171, 177, 179, 181, 311-314, 317, 322-324' 326, 328, 330, 3 3 2- 3 3 7 tested, all compounds showed at least 90% adult mortality. Adult mortality (%) = (number of dead two-pointed spider mites / treated two

Number of leaf mites) xlOO Test Example 2 Test rice seedlings against the control effect of Nilaparvatalugens were immersed in an insecticidal solution adjusted to a concentration of 200 ppm of the compound of the present invention for about 10 seconds, followed by air. Dry, wrap the roots with moisturizing absorbent cotton, and place the rice seedlings in a test tube. Thereafter, 10 nymphs of the second to third instar were released into the tube, covered with gauze, and placed in an incubator under illumination at 25t. At the 5th week after release, the number of dead nymphs was counted and the mortality was calculated by the following formula. The test was carried out using the aforementioned compound numbers 4 8 , 1 3 1 , 3 2 6 , and all the compounds showed a mortality rate of at least 90%.

Mortality (%) = (number of dead insects / number of insects released) xlOO Test Example 3 Against the fall of the long-horned blood scorpion (Haemaphysalis longicornis) / killing effect with a micropipette placed in a petri dish 1 m L of the hair-71 - 201127291 acetone solution of the compound (concentration: l〇mg/mL, 1 mg/mL, 〇·1 mg/mL, 0.01 mg/mL, 0.001 mg/mL) was added to the filter paper. After the filter paper was dried, 100 pups (Haemaphysalis longicornis) were placed in a petri dish and covered with a polyethylene sheet to seal. After 10, 30, 60, and 240 minutes from the placement of the pups, the number of pups that fell over time was recorded. In addition, the number of pups that died over time was recorded after 24, 4, and 72 hours from the placement of the pups. The test was repeated twice. Test Example 4 Using a dog's insecticide test against Haemaphysalis longicornis, a gelatin capsule containing a compound of the present invention at a dose of 10 mg/kg was applied to a dog (Beagle, 8 months old). Immediately after administration, about 50 larvae of Haemaphysalis longicornis were released onto the dog's auricle and artificially parasitized. After treatment, observe the number of parasites, the number of falls, and the mortality of long-term bloody fall. As a result, the compound of the present invention can effectively cause parasitic long-horned blood stasis to fall or die. Test Example 5 Inhibition test using a dog against Ctenocephalides felis A gelatin capsule containing a compound of the present invention at a dose of 10 mg/kg was applied to a dog (Beagle, 8 months old) at the administration. Immediately afterwards, about 1 〇〇 of non-sucking cats were released from the back hair and artificially parasitized. After the treatment -72- 201127291 ‘Return the cat mites with the 蚤 comb and count the number of parasites. As a result, the compound of the present invention can effectively prevent the parasitism of the meerkat. 20 parts by weight 7 parts by weight 5 parts by weight 3 parts by weight 2 parts by weight Now the formulation examples are described below. Formulation Example 1 (1) Compound of the present invention (2) Clay (3) White carbon (4) Sodium polycarboxylate (5) Sodium alkylnaphthalene sulfonate The above components were uniformly mixed to obtain a powder formulation Example 2 (1) 5 parts by weight of the compound of the present invention (2) 60 parts by weight of talc (3) 34.5 parts by weight of calcium carbonate (4) Liquid paraffin 〇 5 parts by weight The above components are uniformly mixed to obtain a powder. Formulation Example 3 20 parts by weight 20 parts by weight 1 〇 parts by weight 2 parts by weight 48 parts by weight (1) The compound of the present invention (2) Ν, Ν-dimethylacetamide (3) Poly ring Ethoxyethane tristyrylphenyl ether (4) Calcium dodecylbenzenesulfonate-73- 201127291 The foregoing components were uniformly mixed and dissolved to obtain an emulsifiable concentrate. Formulation Example 4 (1) Clay 6 8 parts by weight (2) Sodium lignosulfonate 2 parts by weight (3) Polyethylene oxide alkyl aryl sulfate 5 parts by weight (4) White carbon 25 weight A mixture of parts of the foregoing components is mixed with a compound of the invention at a weight ratio of 4:1 to give a wettable powder. Formulation Example 5 (1) 50 parts by weight of the compound of the present invention (2) formaldehyde condensation product of sodium alkylnaphthalenesulfonate 2 parts by weight (3) 0.2 parts by weight of polyoxygenated oil (4) 47.8 parts by weight of water The above components are uniformly mixed and pulverized to obtain a base liquid, and 5 parts by weight of (5) sodium polycarboxylate is added (6) anhydrous sodium sulfate 4 2.8 parts by weight. The mixture is uniformly mixed, granulated and dried to obtain Water - dispersible granules. Formulation Example 6 -74- 201127291 5 parts by weight 1 part by weight 0.1 parts by weight 93.9 parts by weight (1) The compound of the invention (2) Polyethylene oxide octyl phenyl ether (3) Polyepoxy Ethyl alkyl ether phosphate (4) granular calcium carbonate The above components (1) to (3) are uniformly mixed in advance, diluted with an appropriate amount of acetone, and then the mixture is sprayed onto the component (4) to remove the acetone. Get granules. 2.5 parts by weight 2.5 parts by weight 95.0 parts by weight An ultra-low volume formulation was obtained. Formulation Example 7 (1) The compound of the present invention (2) Ν, Ν-dimethylacetamide (3) soybean oil The above components are uniformly mixed and the formulation is dissolved. Example 8 (1) The weight of the compound of the present invention 40 Parts (2) Polyethylene oxide tristyrylphenyl ether potassium phosphate 4 parts by weight (3) Polyoxygenated oil 0.2 parts by weight (4) Xanthan gum 0.1 parts by weight (5) B 5 parts by weight of the diol (6) Water 507 parts by weight The above components were uniformly mixed and pulverized to obtain a suspension concentrate mainly composed of water. -75- 201127291 Formulation Example 9 (1) Compound of the present invention 10 parts by weight (2) Diethylene glycol monoethyl ether 80 parts by weight (3) Polyethylene oxide alkyl ether 1 part by weight The foregoing components were uniformly mixed to obtain a soluble concentrate. The entire disclosure of the Japanese Patent Application No. 2009-242 1 23, filed on Jan. 21, 2009, the entire contents of the entire disclosure of -76-

Claims (1)

201127291 VII. Patent application scope: Its salt: 1 · A diaryl triazole derivative represented by formula (I) Wherein R 1 is an alkyl group which may be substituted by halogen, an alkynyl group which may be substituted by a halogen group or may be halogen; and R 2 is a pyridyl group which may be X-substituted or X-substituted: X is a halogen, an alkyl group, a dilute group, an alkynyl group, an alkoxy group, a haloalkoxy group, an alkylthio group, or a cyano group: each R3 and R4 are independently of each other and are a hydrogen source, an alkenyl group, an alkynyl group or a cyano group; 5 is an alkenyl group which may be substituted by A substituted with A or an alkynyl group which may be substituted by A; A is a halocycloalkyl group; and η is 0, fluorene or 2. 2. The azole derivative or a salt thereof according to the formula (I) of claim 1, wherein the phenyl group which may be substituted by X or which may be substituted by X; An alkyl group, a haloalkyl group, an alkoxy group, a haloalkoxy group, an alkane group, a nitro group or a cyano group; each of R3 and R4 is independent of each other, and is a s-, a phenyl or a cyano group; Replace the yard base, substitute alkenyl. a substituted phenyl group, a haloalkyl group, an amine group, a nitro group, a halogen, a hospital group, a cyano group or a diaryl ternary group; the R 2 system X is a halogen thio group, an amine The base is a gas atom, or may be taken by A-77-201127291 3. The diaryltriazole derivative or a salt thereof according to the formula (I) of claim 2, wherein each R3 and r4 are independent of each other Is a halogen, alkyl or cyano group; and R5 is an alkyl group which may be substituted by A. 4. The diaryltriazole derivative or a salt thereof according to the formula (1) of the patent application, wherein R2 is a pyridyl group which may be substituted by X. 5. As in the scope of claim 4 ( a diaryltriazole derivative or a salt thereof, wherein the X-substituted pyridyl group is a 2-pyridyl group which may be substituted by X. 6. The formula (I) of claim 1 a diaryltriazole derivative or a salt thereof, wherein the η system is 0. 7. An insecticide, acaricide, nematicide or soil pesticide, which contains the second item as claimed in claim 1 a triazole derivative or a salt thereof as an active ingredient. 8. The insecticide, acaricide, nematicide or soil pesticide according to item 7 of the patent application, wherein the diaryl triazole derivative or a salt thereof Insecticides, acaricides, nematicides or soil pesticides as active ingredients for agricultural and horticultural use. 9 - Insecticides or acaricides for agricultural and horticultural use, as in claim 8 Containing a diaryltriazole derivative or a salt thereof as an active ingredient. 10. An insecticide according to item 7 of the patent application or An elixir, wherein the diaryltriazole derivative or a salt thereof is used as an active ingredient as an insecticide, acaricide, nematicide or soil pesticide for controlling animal parasites or cockroaches - 78-201127291 The aryl group of the azole, the worm, the nematode or the soil pest contains an effective amount thereof as claimed in the first bis derivative of the patent application or a salt thereof. ) a diaryl tri η W organism or Wherein R1 is an alkyl group which may be substituted by halogen, an alkynyl group which may be substituted by halogen or a light halogen; and R2 is a phenyl group which may be substituted by X or a pyridyl group which may be substituted by X; Halogen, alkyl, haloalkylalkenyl 'alkynyl, alkoxy, haloalkoxy, alkylthio, amine, nitro or alkoxy; each R3 and R4 are independently of each other and are hydrogen An atom, a halogen, a hospital group, a stilbene group, an alkynyl group or a cyano group; R 5 is an alkyl group which may be substituted by A, an alkenyl group which may be substituted by A, or an alkynyl group which may be substituted by A; a is a halogen, cyanide a base or a ring-based base; and the η system is 0, 1, or 2, the method comprising (1) a compound of the formula (Π): -79- 201127291 Wherein R1, R3, R4, R5 and η are as defined above, and are reacted with a compound of formula (III): R2CHO wherein R2 is as defined above to give a compound of formula (IV): Wherein R1, R2, R3, R4, R5 and η are as defined above and dehydrogenated; or (2) reacting a compound of formula (II) with a compound of formula (V): R2C0C1, wherein R2 Is defined as defined above; or (3) oxidizing the compound of formula (Ia): R4 (I-a) wherein R1, R2, R3, R4 and R5 are as defined above; or (4) halogenating a compound of formula (I-c): -80- 201127291 S(0)nR5c (Ic) wherein R1, R2, R1, R2 and n are as defined above; R5c is an alkyl group which may be substituted with A1, an alkenyl group which may be substituted by Ai, or may be substituted by A; Alkynyl' and A1 are halogen, cyano or cycloalkyl; or (5) compounds of formula (VI): 0 R4 (VI) wherein R1, R3, R1 and R2 are as defined above or a compound of the formula (χιν): (XIV) -81 - 1 wherein R1, R3, R1 and R2 are reacted as defined above with a compound of formula (VII) 2: VL1, wherein r4 is as defined above and 3 4 L 1 is Detached from the base. 201127291 IV. Designated representative: (1) The designated representative of the case is: None (2) The symbol of the symbol of the representative circle is simple: No. 5. If there is a chemical formula in this case, please disclose the chemical formula that best shows the characteristics of the invention: I) -4-