TW201029575A - Triazolopyrimidine derivative or its salt, process for producing the same and pesticide containing the same - Google Patents

Abstract

To provide a novel pesticide. A triazolopyrimidine derivative represented by the formula (I) or its salt: wherein R1 is alkyl which may be substituted, cycloalkyl which may be substituted, alkenyl which may be substituted, alkynyl which may be substituted, halogen, cyano, aryl or the like; and Het is substituted heterocycle group, provided that excluded are (1) a case where R1 is methyl, and Het is 5-hydroxy-3-methyl-1-phenyl-pyrazol-4-yl, (2) a case where R1 is phenyl, and Het is 1-ethyl-pyrazol-4-yl, (3) a case where R1 is methyl, and Het is thiophen-2-yl substituted by alkyl and (4) a case where R1 is trifluoromethyl, and Het is thiophen-2-yl substituted by alkyl.

Description

201029575 SUMMARY OF THE INVENTION [Technical Field] The present invention relates to an insecticide containing a novel triazolopyrimidine derivative or a salt thereof as an active ingredient. [Prior Art] Patent Document 1 discloses that a specific 7-heteroaryl [1,2,4]triazolo[l,5-a] φ pyrimidine can be used as a medicament. However, the compounds of the present invention are not specifically described in Patent Document 1. Patent Document 2 discloses an insecticide containing a pyridyl-triazolopyrimidine derivative as an active ingredient. However, the compound described in Patent Document 2 is different from the compound of the present invention because in Patent Document 2, the Het moiety in the formula (I) mentioned below is a pyridyl group. Patent Document 1: U.S. Patent No. 4,444,774, Patent Document 2: W02008/099902 〇 [Summary of the Invention] The object of the present invention has been to use many insecticides for many years, but many of them have various problems. Insufficient efficacy, limited use of pests due to their resistance to drugs. It is therefore desirable to develop novel insecticides that do not have such problems in nature, such as insecticides that can control a variety of pests that cause problems in agricultural and horticultural fields, or insecticides that can control pests that are parasitic on animals. . Means for achieving the object -5- 201029575 The present inventors have conducted various studies on triazolopyrimidine derivatives in an effort to find an excellent insecticide. As a result, novel triazolopyrimidine derivatives have been found which have extremely high insecticidal effects against pests at low doses and are safe against crops, natural enemies of mammals or mammals. Therefore, the present invention has been completed. Namely, the present invention relates to an insecticide containing a triazolopyrimidine derivative of the formula (I) or a salt thereof as an active ingredient:

Wherein R1 is an alkyl group which may be substituted by A, a cycloalkyl group which may be substituted by A, an alkenyl group which may be substituted by A, an alkynyl group which may be substituted by A, a halogen, a cyano group, an aryl group, a 1,3-di Oxolane, COR2, S(O) nR3' NR3R4 or CONR3R4; Het is ^£^(X)W, ^^(Xjw2 Het1 Het2, Het3 % Het4 ^ , or 〇(X)w ( X)w1 Het5 (X)w1 Het6 Het7

A is halogen, OR2, alkyl or ring-based; R2 is hydrogen 'alkyl, halogen-based, ortho-oxy or nr3r4; r3 is hydrogen or affinity; r4 is hydrogen, alkyl, halogen Alkyl group, alkyl group, alkoxycarbonyl group, _ sylylene base-6- 201029575 or haloalkoxycarbonyl; X is alkyl, alkenyl, alkynyl, aryl, halogen, haloalkyl, cyanide Base, nitro, NR3R4, S ( Ο ) nR3, OR2 or COR2; Y is oxygen, sulfur or NR5; R5 is alkyl, haloalkyl, cycloalkyl or aryl; η is 〇 to 2 An integer; wl is an integer from 1 to 3; w2 is an integer from 1 to 2; and when the case is wi or w2 is at least 2, the plurality of Xs may be the same or different, with the constraint that the following is excluded: 1) R1 is methyl 'and Het is 5-hydroxy-3-methyl-1-phenyl-pyrazole-0 core' (2) Rl is phenyl and Het is 1-ethyl -pyrazol-4-yl'(3) R1 is a methyl group, and Het is an alkyl-substituted thiophen-2-yl' and (4) R1 is a trifluoromethyl group, and Het is an alkane Substituted thiophen-2-yl. EFFECTS OF THE INVENTION The insecticide containing the triazolopyrimidine derivative of the above formula (I) or a salt thereof as an active ingredient has an extremely high insecticidal effect against pests at a low dose. BEST MODE FOR CARRYING OUT THE INVENTION In the formula (I), the number of the substituents X or A may be 1 or at least 2, and when it is at least 2, the substituents may be the same or different. In addition, each X or A substitution position may be any position. As the halogen in the formula (I), an atom of fluorine, chlorine, bromine or iodine can be mentioned. The number of halogen atoms as a substituent may be 1 or at least 2, and when at least 2, the individual halogen atoms may be the same or different. Further, the substitution position of each halogen atom may be any position. 201029575 In formula (I), the alkyl group may be a straight or branched chain. As a specific example of the alkyl group, a C!-6 alkyl group such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, a pentyl group or a hexyl group can be mentioned. In the formula (I), as the cycloalkyl group, 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. In the formula (I), the alkenyl group may be a straight chain or a branched chain. As a specific example of the alkenyl group, 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. In the formula (I), the alkynyl group may be a straight chain or a branched chain. As a specific example of the alkynyl group, 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. In the formula (I), as the aryl group, for example, a C6_1() aryl group such as a phenyl group or a naphthyl group can be mentioned. The salt of the triazolopyrimidine derivative of the above formula (I) includes all types as long as it is of a type acceptable in the art. For example, a table salt such as a dimethylammonium salt or a trimethylammonium salt; a mineral acid salt such as a hydrochloride, a perchlorate, a sulfate or a nitrate; or an organic acid salt such as an acetate or Methanesulfonate. The tri-wam-pyrimidine derivatives of formula (I) may have certain isomers, such as optical isomers or geometric isomers, and such isomers and mixtures of such isomers are included in In the invention. In the present specification, the isomers are described as a mixture unless otherwise stated. Further, in the present invention, various isomers other than the foregoing may be included in the scope of ordinary knowledge in the technical field. Further, depending on the type of isomer, it may have a chemical structure different from that of the formula -8-201029575 (I), however, those skilled in the art will be fully aware that the compounds are isomers of the compound of the present invention, apparently Compounds and the like are included in the scope of the present invention. The triazolopyrimidine derivative of the formula (I) or a salt thereof can be obtained by the following processes [1] to [8] and a general method for producing a salt. Further, the triazolopyrimidine derivative of the formula (I) or a salt thereof can be produced according to the synthesis examples mentioned below. Now, each manufacturing method will be described in detail with reference to a reaction flow chart.

In the process [1], 111!1 is an alkyl group which may be substituted by A1, a cycloalkyl group which may be substituted by A1, an alkenyl group which may be substituted by A1, an alkynyl group which may be substituted by A1, or an aryl group; R6 and R7 are each independently alkyl; A1 is 〇R2a, alkyl or cycloalkyl; R2a is hydrogen, alkyl or haloalkyl; and Het is as previously mentioned. Process [1] is a process for producing a triazolopyrimidine derivative of the formula (1-1) from the compound of the formula (II), and comprising the above steps 1 and 2. In the first step of the process [1], the compound of the formula (II) and the compound of the formula (III) are condensed to form an α,/3-unsaturated ketone derivative of the formula (IV). The compound of the formula (ΙΠ) may be used in a proportion of from 1 to 5 equivalents, preferably from 3 to 3 equivalents per 1 mole of the compound of the formula (II). This 201029575 reaction can be carried out in the presence of a solvent, if necessary. The solvent is not particularly limited as long as the reaction is not impaired. For example, mention may be made of alcohols such as methanol, ethanol, propanol or butanol; aromatic hydrocarbons such as benzene, toluene or xylene; aliphatic hydrocarbons such as pentane, hexane, heptane, petroleum ether, light gasoline or Petroleum essence; ether, such as diethyl ether, dipropyl ether, dibutyl ether, tetrahydrofuran or dioxane; esters such as methyl acetate or ethyl acetate; nitriles such as acetonitrile or propionitrile; acid amines such as N, N-dimethylformamide, hydrazine, hydrazine-dimethylacetamide or N-methylpyrrolidone; and hydrazine, such as dimethyl argon; hydrazine, such as butyl sulphate; guanidinium phosphate, such as Hexamethylphosphonium; a halogenated hydrocarbon such as chloroform, dichloromethane, carbon tetrachloride or 1,2·dichloroethane; or a mixed solvent thereof. The reaction temperature is usually from 80 to 200 ° C, preferably from 100 to 150 ° C. The reaction time is usually from 3 to 48 hours. After the termination of the step 1 of the process [1], the step 2 of the process [1] can be continuously carried out without separately separating the compound of the formula (IV). In the step 2 of the process [1], the compound of the formula (IV) and the compound of the formula (V) are condensed to form a compound of the formula (1-1). The compound of the formula (V) may be used in a proportion of from 1 to 10 equivalents, preferably from 1 to 2.5 equivalents per 1 mole of the compound of the formula (IV). This reaction can usually be carried out in the presence of a solvent. The solvent is not particularly limited as long as the reaction is not impaired. For example, mention may be made of carboxylic acids such as acetic acid or propionic acid, alcohols such as methanol, ethanol, propanol or butanol; aromatic hydrocarbons such as benzene, toluene or xylene; aliphatic hydrocarbons such as pentane, hexane, Heptane, petroleum ether 'light gasoline or petroleum spirit; ether, such as diethyl ether, dipropyl ether, dibutyl ether, tetrahydrofuran or dioxane; esters such as methyl acetate or ethyl acetate; nitriles such as acetonitrile or propyl Nitrile; acid amide, such as hydrazine, hydrazine-dimethylformamide, N,N-dimethylacetamide-10-201029575 or N-methylpyrrolidone; and hydrazine, such as dimethylhydrazine Milling, such as cyclobutyl hydrazine; guanidinium phosphate, such as hexamethylphosphoniumamine; halogenated hydrocarbon such as chloroform, dichloromethane, carbon tetrachloride or 1,2-dichloroethane; or a mixed solvent thereof. Among them, the carboxylic acid is particularly preferred. The reaction temperature is usually from 50 to 150 ° C, preferably from 80 to 120 ° C. The reaction time is usually from 30 minutes to 1 hour. Process [2]

❹ In the process [2], R3a is an alkyl group; Z is a leucoside; and Het is as mentioned above. As the halogen of Z, an atom of fluorine, chlorine, bromine or iodine can be mentioned. Process [2] is a process for producing a triazolopyrimidine derivative of the formula (1-2) from the compound of the formula (II), and comprising the above steps 1 and 2. In the first step of the process [2], the compound of the formula (II), carbon disulfide and the compound of the formula (VI) are reacted to form an α:, /3-unsaturated ketone derivative of the formula (VII). The carbon disulfide and the compound of the formula (VI) may be used in a proportion of 1 to 5 equivalents, preferably 1 to 3 equivalents per 1 mole of the compound. This reaction can usually be carried out in the presence of a base and a solvent. The base may, for example, be an alkali metal hydride such as sodium hydride or potassium hydride; an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide; an alkali metal such as sodium or potassium; or an alkali metal alkoxide-11 - 201029575, such as Sodium methoxide, sodium ethoxide or potassium butoxide. The base can be used in an amount of from 1 to 10 equivalents, preferably from i to 3 equivalents per 1 mole of the compound. The solvent is not particularly limited as long as the reaction is not impaired. For example, the same solvents as mentioned in the step 1 of the process [1] can be mentioned. The reaction temperature is usually from 0 to 10 ° C, preferably from 10 to 50 ° C. The reaction time is usually from 6 to 48 hours. In step 2 of Process [2], the compound of formula (VII) and the compound of formula (V) are condensed to form a compound of formula (1-2). The compound of the formula (V) may be used in a proportion of from 1 to 5 equivalents, preferably from 1 to 3 equivalents per 1 mole of the compound of the formula (VII). This reaction can usually be carried out in the presence of a base and a solvent. The base may, for example, be an alkali metal hydride such as sodium hydride or potassium hydride; an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide; a base metal such as sodium or potassium; or an alkali metal alkoxide such as sodium methoxide or ethanol. Sodium or potassium butoxide; an alkali metal carbonate such as sodium carbonate or potassium carbonate; an alkali metal hydrogencarbonate such as sodium hydrogencarbonate or potassium hydrogencarbonate; or an organic base such as triethylamine or pyridine. The base may be used in an amount of from 1 to 5 equivalents, preferably from 1 to 3 equivalents per 1 mole of the compound of the formula (VII). The solvent is not particularly limited as long as the reaction is not impaired. For example, the same solvent as mentioned in the step 1 of Process [1] can be mentioned. Among them, acid amide is preferred. The reaction temperature is usually from 100 to 200 °C. The reaction time is usually from 5 minutes to 10 hours. -12- 201029575 Process [3] (1-2)

S(〇)mR3a In the formula (1-2) of the process [3], Het and R3a are as described above; and 1^ is an integer of 1 or 2. In the process [3], the compound of the formula (1-2) and the oxidizing agent are reacted to form a triazolopyrimidine derivative of Φ(I-3). The oxidizing agent can be, for example, hydrogen peroxide, peracetic acid or m-chloroperbenzene. This reaction can usually be carried out in the presence of a solvent. The reactant is not particularly limited as long as it does not damage the reactants. For example, mention may be made of halogenated hydrocarbons such as chloroform, dioxane, carbon tetrachloride or 1,2-dichloroethane; ketones such as acetone or methyl ketone; ethers such as diethyl ether, dipropyl ether, dibutyl ether , tetrahydrofuran or an alkane; a carboxylic acid such as acetic acid or propionic acid; or a mixed solvent thereof. The oxidation is used in a ratio of 1 to 3 equivalents per 1 mole of the compound (1-2). The reaction temperature is usually from 15 ° C to the reflux temperature. The reaction time is usually 24 hours. Process [4] Nucleophilic reagent (1-3) - Process [4], Rb is an alkyl group which may be substituted by A1, may be substituted by a cycloalkyl group, may be substituted by A1, may be used The A1 substituted alkyne refers to the form of formic acid, and the chloromethylethyl dioxor is available. 1 to

. A group, -13- 201029575 halogen, cyano, aryl or NR3R4; and formulas (1-3), Het, A1, R3 and R4 are as mentioned above. The compound of the formula (1-3) and the nucleophilic reagent in the process [4] are reacted to form a triazolopyrimidine derivative of the formula (1-4). The nucleophilic reagent can be, for example, a primary or secondary amine such as methylamine, dimethylamine or piperidine; an organometallic reagent such as methylmagnesium bromide, ethylmagnesium bromide, vinylmagnesium bromide, brominated 1 -butenyl zinc, zinc 1-propynyl zinc or phenyl magnesium bromide; halogenating agent such as potassium fluoride, fluorinated planer, tetrabutyl fluorinated, lithium chloride or sodium bromide; or metal cyanide a compound such as sodium cyanide, potassium cyanide or copper cyanide. The nucleophilic reagent may be used in an amount of from 1 to 5 equivalents, preferably from 1 to 3 equivalents per 1 mole of the compound of the formula (1-3). The reaction can usually be carried out in the presence of a solvent. The solvent is not particularly limited as long as the reaction is not impaired. For example, mention may be made of alcohols such as methanol, ethanol, propanol or butanol; aromatic hydrocarbons such as benzene, toluene or xylene; aliphatic hydrocarbons such as pentane, hexane, heptane, petroleum ether, light gasoline or Petroleum essence; ether, such as diethyl ether, dipropyl ether, dibutyl ether, tetrahydrofuran or dioxane; esters such as methyl acetate or ethyl acetate; nitriles such as acetonitrile or propionitrile; acid amines such as N, N-dimethylformamide, N,N-dimethylacetamide or N-methylsarozolone; and Yafeng' such as dimethyl sulfite; or a mixed solvent thereof. The reaction temperature is usually -100 to 501, preferably -70 to 30 °C. The reaction time is usually from 1 minute to 48 hours. -14- 201029575 Process [5]

Step 1 r1cco2r8 01)

Step 2 (K)

In process [5], R1. Is an alkyl group which may be substituted by hydrazine 1, a cycloalkyl group which may be substituted by hydrazine 1, an alkenyl group which may be substituted by A1, an alkynyl group which may be substituted by A1, an aryl group or an aryl group; R8 is an alkyl group; and Het and A1 As mentioned before. Process [5] is a process for producing a triazolopyrimidine derivative of the formula (1-5) from a compound of the formula (II), and comprising the above steps 1 and 2. In step 1 of Process [5], a compound of formula (Π) and a compound of formula (VIII) are reacted to form a compound of formula (IX). The compound of the formula (VIII) can be used in a proportion of from 1 equivalent to an excess, preferably from 1 to 10 equivalents per 1 mole of the compound of the formula (II). The reaction can usually be carried out in the presence of a base and a solvent. The same base as mentioned in the step 1 of the process [2] can be mentioned. The base may be used in an amount of from 1 to 5 equivalents, preferably from 1 to 2 equivalents per 1 mole of the compound. The solvent is not particularly limited as long as the reaction is not impaired. For example, mention may be made of alcohols such as methanol, ethanol, propanol or butanol; aromatic hydrocarbons such as benzene, toluene or xylene; aliphatic hydrocarbons such as pentane, hexane, heptane, petroleum ether, light gasoline or Petroleum essence; ethers such as diethyl ether, dipropyl ether, dibutyl ether, tetrahydrofuran or dioxane; acid amines such as N,N-dimethylformamide, hydrazine, hydrazine-dimethylacetamide or Ν-methylpyrrolidone; argon, such as dimethyl hydrazine; maple, such as cyclazone; halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride or 1,2 - di-15- 201029575 An alkane; or a mixed solvent thereof. Wherein ' is preferred as ether. The reaction temperature is usually from 0 to 100. (:, preferably 10 to 80 ° C. The reaction time is usually 5 minutes to 24 hours. After the termination of the step 1 of the process [5], the process 2 of the process [5] can be continuously performed instead of the single type (IX). The compound of the formula (IX) and the compound of the formula (V) are condensed in the step 2 of the process [5] to form a compound of the formula (1-5). The compound of the formula (V) can be used in a ratio of 1 mole per mole. The compound of the formula (IX) has 1 to 10 equivalents, preferably 1 to 5 equivalents. The reaction is usually carried out in the presence of a solvent, and the solvent is not particularly limited as long as the reaction is not impaired. For example, the procedure of the process can be mentioned. The same solvent as mentioned in 2, wherein the carboxylic acid is preferred. The reaction temperature is usually from 50 to 200 ° C, preferably from 80 to 15 (TC. The reaction time is usually from 30 minutes to 1 hour. Process [6]

(1-5) In the process [6], R9 is the yard base; and Het and Rle are as mentioned above. Process [6] is a process for producing a triazolopyrimidine derivative of the formula (^5) from the compound of the formula (X), and comprising the above steps 1 and 2. In the step 1 of the process [6], the compound of the formula (X) and the compound of the formula (ΧΙ) are reacted to form a compound of the formula (IX). The compound of the formula (XI) can be used in a proportion of from 1 equivalent to an excess, preferably from 1 to 10 equivalents per 1 mole of the compound of the formula (X). This reaction can usually be carried out in the presence of a base and a solvent. As the base, for example, the same base as mentioned in the step 1 of the process [2] can be mentioned. The base may be used in an amount of from 1 to 5 equivalents, preferably from 1 to 2 equivalents per 1 mole of the compound of the formula (X). The solvent is not particularly limited as long as the reaction is not impaired. For example, the same solvent as mentioned in the step 1 of the process [5] may be mentioned, wherein the ether is preferred. The anti-φ should be usually from 〇 to loot: preferably from 10 to 80 °C. The reaction time is usually from 5 minutes to 24 hours. In the step 2 of the process [6], the compound of the formula (IX) and the compound of the formula (V) are condensed to form a compound of the formula (1-5). The reaction can be carried out in the same manner as in step 2 of the process [5].

Process [7]

In the process [7], R1() and R11 are each independently hydrogen, alkyl or cycloalkyl; Q is halogen; and Het is as mentioned above. In the process [7], the compound of the formula (1-6) and a halogenating agent are reacted to form a triazolopyrimidine derivative of the formula (1-7). The halogenating agent may, for example, be N-chlorosuccinimide, N-bromosuccinimide or N-iodosuccinimide. The halogenating agent can be used in an amount of from 1 to 5 equivalents per 1 mole of the compound of the formula (1-6), preferably from 1 to 2 equivalents, -17 to 201029575. The reaction can usually be carried out in the presence of a free radical initiator. The radical initiator can be, for example, benzammonium peroxide or 2,2'-azobis(isobutyronitrile). The reaction can be carried out under light if necessary. The reaction can usually be carried out in the presence of a solvent. The solvent is not particularly limited as long as the reaction is not impaired. For example, a halogenated hydrocarbon such as chloroform, methylene chloride, carbon tetrachloride or 1,2-dichloroethane may be mentioned. The reaction temperature is usually from 〇 to 1 ° C. The thickness is preferably from 10 to 8 (TC. The reaction time is usually from 5 minutes to 24 hours.

Process [8]

(XIV)

1d Het-B(R13)p (XV) Process [8] 'Rld is an alkyl group which may be substituted by A, a cycloalkyl group which may be substituted by A, an alkenyl group which may be substituted by A, and may be substituted by A. Alkynyl' or aryl; Q1 is halogen; R13 is OH, alkyl, cycloalkyl, alkoxy@yl or fluoro; when R13 is OH, alkyl, cycloalkyl or alkoxy, p Is 2' and when R13 is fluorine, p is 3; the alkyl or alkoxy group of Ri3 may be bonded to each other together with adjacent boron atoms to form a ring; and Het and A are as mentioned above. In the process [8], the compound of the formula (XIV) and the boron compound of the formula (?ν) are subjected to a Suzuki coupling reaction in the presence of a transition metal catalyst to form a triazolopyrimidine derivative of the formula (8).

Suzuki coupling reactions have been studied in many publications, -18 - 201029575 The 'Suzuki coupling reaction in the steps of the invention can be carried out according to known methods (eg ' Synth. Commun·, 1 98 1,1 1 ( 7 ) , 5 1 3 -5 1 9 or Synl ett., 1 992, 207-21 0 method). Since the substituted boron moiety _ BF3 group represented by B(R13) p in the formula (XV) (wherein R 13 is fluorine and the p system is 3) has a negative charge, the BF 3 group is usually associated with an alkali metal such as potassium. ) formation of trifluoroborate. The substituted boron represented by B(R13)p in the formula (XV) may be, for example, a hydroxy boron, a ruthenium-based boron 'homocarbo-boron or a trifluoro sulfonate. The boron compound in the formula (XV) may be used in a proportion of 0.5 to 1 equivalent per 1 mol of the compound of the formula (XIV), preferably 0.5 to 0.8 equivalent. The transition metal catalyst used in the reaction is a complex of a transition metal compound or a transition metal compound and optionally a ligand. For example, palladium-carbon (Pd/C), tetrakis(triphenylphosphine)palladium (ruthenium), bis(dibenzylideneacetone)palladium(0), tetrakis(dibenzylideneacetone)dipalladium (0) may be mentioned. ), palladium (II) acetate-triphenylphosphine or palladium (II) acetate-tricyclohexylphosphine. In the case of a mismatched φ, (1) a pre-isolated complex may be used, or (2) a transition may be used in which the transition metal compound and the ligand are mixed in a solvent selected as appropriate and are not separated. Compound. The transition metal catalyst can be used in a proportion of from 0.001 to 0.2 equivalents per 1 mole of the compound of the formula (XIV), preferably from 0.01 to 0.1 equivalents. The reaction can usually be carried out in the presence of a base. The base may, for example, be an alkali metal carbonate such as sodium carbonate, potassium carbonate or carbonic acid; an alkali metal hydrogencarbonate such as sodium hydrogencarbonate; an alkaline earth metal carbonate such as calcium carbonate; an alkali metal hydroxide such as sodium hydroxide or Potassium hydroxide; alkaline earth metal hydroxide, -19· 201029575 such as calcium hydroxide; alkali metal fluorides such as fluorinated planer or potassium fluoride; or organic bases such as triethylamine, pyridine or 4-(Ν, Ν-Dimethylamino)pyridine. The base may be used in an amount of from 1 to 20 equivalents per 1 mol of the compound of the formula (XIV), preferably from 1 to 3 equivalents. The reaction can usually be carried out in the presence of a solvent. The solvent is not particularly limited as long as the reaction is not impaired. For example, mention may be made of water; alcohols such as methanol, ethanol, propanol or butanol; aromatic hydrocarbons such as benzene, toluene or xylene; aliphatic hydrocarbons such as pentane, hexane, heptane, petroleum ether, light Gasoline or petroleum spirit; ethers such as diethyl ether, dipropyl ether, dibutyl ether, tetrahydrofuran, dioxane, ethylene glycol dimethyl ether; nitriles such as acetonitrile or propionitrile; halogenated hydrocarbons such as chloroform, dichloro Methane, carbon tetrachloride or 1,2-dichloroethane; or a mixed solvent thereof. The reaction temperature is usually from 15 ° C to the reflux temperature of the reaction mixture, preferably from 40 ° C to the reflux temperature of the reaction mixture. The reaction temperature varies depending on the reaction temperature, the amount of the reactant, the reaction pressure, and the like, however, it is usually from 1 to 96 hours. The boron compound in the formula (XV) is commercially available or can be synthesized by a known method. For example, a boron compound can be synthesized by reacting a halogen derivative (preferably a bromine derivative) with trimethyl borate in the presence of a base such as t-butyllithium in the aforementioned individual process for the process [1] or Process [6] is particularly good. For example, the compound of formula (XIV) in Process [8] can be obtained by the following process [A]. -20- 201029575 Process [A]

(ΧΠ)

Halogenation reaction Step 2 (Xffl)

(XN) In the process [A], 'R12 is an alkyl group; and Rld and Q1 are as mentioned above. As the halogen of Q1, each atom of chlorine, bromine and iodine can be mentioned. Process [A] is a process for producing a compound of the formula (XIV) from a compound of the formula (XII) and comprising the above steps 1 and 2. In the step 1 of the process [A], the compound of the formula (XII) and the compound of the formula (v) are condensed to form a compound of the formula (XIII). The compound of the formula (V) may be used in a proportion of usually 1 to 1 equivalent, preferably 1 to 3 equivalents per 1 mole of the compound of the formula (XII). The reaction can usually be carried out in the presence of a solvent. The solvent is not particularly limited as long as the reaction is not impaired. For example, mention may be made of a carboxylic acid 'such as acetic acid or propionic acid; an alcohol such as methanol, ethanol, propanol or butanol; an ester such as methyl acetate or ethyl acetate; a nitrile such as acetonitrile or propionitrile; Such as hydrazine, hydrazine-dimethylformamide, hydrazine, hydrazine-dimethylacetamide or hydrazine-methylpyrrolidone; alum, such as dimethyl sulfoxide; maple, such as cyclobutyl hydrazine; Such as hexamethylphosphonamide; or a mixed solvent thereof. Among them, the carboxylic acid is particularly preferred. The reaction temperature is usually from 50 to 150 ° C, preferably from 80 to 120 ° C. The reaction time is usually from 30 minutes to 100 hours. Step 2 of Process [A] is a step of halogenating a compound of the formula (XIII), and comprises: -21 - 201029575 (a) reacting a compound of the formula (XIII) with a chlorinating agent or a brominating agent to form a formula (XIV) a step of the compound (where Qi is chlorine or bromine), and (b) reacting the compound of formula (XIV) formed by (a) (wherein Q1 is chlorine or bromine) with ammonia, and then The step of reacting with an iodinating agent in the presence of a nitriding agent to form a compound of the formula (XIV) wherein Q1 is iodine. Now, each of the steps (a) and (b) will be described in detail. (a) The chlorinating agent may be, for example, phosphonium chloride, phosphorus trichloride or phosphorus pentachloride. The brominating agent can be, for example, phosphonium bromide, phosphorus tribromide or phosphorus pentabromide. The chlorinating agent or brominating agent may be used in a ratio of 2 to 3 equivalents per 1 mole of the compound of the formula (XIII). This reaction can be carried out in the presence of a solvent as the case requires. The solvent is not particularly limited as long as the reaction is not impaired. For example, a halogenated hydrocarbon such as dichloromethane can be mentioned. The reaction temperature is usually from 〇 ° C to the reflux temperature of the reaction mixture, preferably from 20 ° C to the reflux temperature of the reaction mixture. The reaction time is usually from 1 to 48 hours. Step (b) comprises a previous reaction in which a compound of the formula (XIV) formed in the step (a) wherein Q1 is chlorine or bromine is reacted with ammonia; and a reaction is carried out later, wherein the compound formed and the iodinating agent are heavy Reaction in the presence of a nitriding agent. The previous reaction in (b) can usually be carried out in the presence of a base. It is especially good to use excess ammonia, which can also be used as a hydrazine. The previous reaction in (b) can usually be carried out in the presence of a solvent. The solvent is not particularly limited as long as the reaction is not impaired. For example, mention may be made of aromatic hydrocarbons such as benzene, toluene or xylene; aliphatic hydrocarbons such as pentane, hexane, heptane, petroleum ether, light gasoline or petroleum -22-201029575; halogenated hydrocarbons such as chloroform , dichloromethane, carbon tetrachloride or dichloroethane; or a mixed solvent thereof. The reaction temperature is usually from 20 ° C to the reflux temperature of the reaction mixture, preferably from 40 ° C to the reflux temperature of the reaction mixture. The reaction time is usually from 2 to 48 hours. In the later reaction of (b), the diazotizing agent may, for example, be an alkyl nitrite as it is used, wherein 'isoamyl nitrite is preferred. The diazotizing agent can be used in a ratio of from 1 to 5 equivalents per 1 mole of the compound of the formula (XIV) wherein the Qi is a chlorine Φ or a bromine atom. The iodinating agent can be, for example, iodine or diiodomethane. The iodinating agent can be used in a proportion of from 5 to 5 equivalents per 1 mole of the compound of the formula (XIV) wherein the Q1 is a chlorine or a bromine atom. The reaction later in (b) can usually be carried out in the presence of a solvent. The solvent is not particularly limited as long as the reaction is not impaired. For example, mention may be made of aliphatic hydrocarbons such as pentane, hexane, heptane, petroleum ether, light gasoline or petroleum spirit; ethers such as diethyl ether, dipropyl ether, dibutyl ether, tetrahydrofuran or dioxins An alkane; an ester such as methyl acetate or ethyl acetate; a nitrile such as acetonitrile or propionitrile; or a mixed solvent thereof. When an alkyl nitrite is used as the diazotizing agent, diiodomethane as an iodinating agent can be used as a secondary solvent. The reaction temperature is usually from 60 to 120 ° C', preferably from 70 to 10 ° C. The reaction time is usually from 1 to 48 hours. Hereinafter, preferred embodiments of the insecticide containing the compound of the present invention will be described. The insecticide containing the compound of the present invention is particularly useful as, for example, an agent for controlling various pests which are problematic in the agricultural and horticultural fields, that is, agricultural and horticultural insecticides, or as an agent for controlling pests parasitic on animals, that is, against animals. The insecticide of the parasite on the body. -23- 201029575 Agricultural and horticultural insecticides containing the compounds of the present invention can be used as insecticides, acaricides, nematicides or soil insecticides, and are effective for controlling plant parasitic wovens, such as two-spotted spider mites ( Tetranychus urti cae ), Tetranychus cinnabarinus, T etranychus kanzawai, Panonychus citri, Panonychus ulmi, Polyphagotarsonemus latus, mandarin Aculops pelekassi and rhizoglyphus echinopus; budworms such as Myzus persicae and Aphis gossypii; agricultural insect pests such as Plutella xylostella and Mamestra Brassicae), Spodoptera litura, cydia pomonella, Heliothis zea, Heliothis virescens, Lymantria dispar, Cnaphalocrocis medinalis, Adoxophyes sp., Leptinotarsa decemlineata, Aculc Ophora femoralis), ringworm weevil (Anthonomus grandis), hunting zen, leafhopper, scale insect, bed bug, whitefly, thrips, grasshopper, flower fly, scarab, Agrotis ipsilon, cutting root Agrotis segetum and ants; plant-parasitic nematodes such as Rhizobium nematode, cyst nematode, root rot nematode, Aphelenchoides besseyi, Nothotylenchus acris, and Bursaphelenchus xylophilus Gastropods, such as insects and snails; soil pests, such as isopods, such as tide worms ( -24- 201029575)

Armadillidium vulgare and Porcellio scaber; hygienic insect pests such as tropical rat aphids (0rnith〇nyssus bacoti), bee stings, mulberry (Musca domestica) and house mosquitoes (Culex pipiens); storage of grain insect pests such as Maito moth (Sitotr〇ga cerealella), red bean weevil (Callosobruchus chinensis), Tribolium castaneum and mealworm; houseware insect pests such as Tinea pellionella, Stupidus japonicus And terrestrial white pelicans; woven in the room, such as Tyrophagus putrescentiae, Dermatophagoides farinae, Chel acaropsis moorei and so on. Among them, agricultural and horticultural insecticides containing the compound of the present invention are particularly useful for controlling plant parasitic mites, agronomic insect pests, plant-borne nematodes or the like. In particular, it can more effectively control plant parasitic cockroaches and agronomic 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 organic dish, urethane, synthetic pyrethroid and/or neonicotinoid insecticide. Moreover, the compound of the present invention has excellent systemic insecticidal properties, and by applying the agricultural and horticultural insecticide containing the compound of the present invention to the soil treatment, it is possible to control not only harmful insects in the soil, harmful mites, harmful nematodes, harmful gastropods. And harmful isopods can also control leaf pests. Another preferred embodiment of the insecticide containing the compound of the present invention may be an agricultural and horticultural insecticide for controlling the above-mentioned plant parasitic cockroaches, agronomic insect pests, plant parasitic nematodes, gastropods and soil pests in a holistic manner. . The agricultural and horticultural insecticides containing the compound of the present invention are usually formulated by mixing the compound with various agronomic additives, and are used in the form of a formulation such as a powder, granules, powder granules, water-dispersible granules, Wettable powder, water-based suspension concentrate, oil-based suspension concentrate, water-soluble powder, water-soluble granule, emulsifiable concentrate, soluble concentrate, paste, aerosol, oil solution, hair Smoke insecticides, microcapsules 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 additives include solid carriers such as diatomaceous earth, calcium carbonate 'talc, kaolin, bentonite, sericite, clay, zeolite, pumice, quartz sand, bun iron, white carbon, sodium carbonate, sodium sulfate, ammonium sulfate, Urea, starch and sugar; solvent such as water, xylene, C1Q alkylbenzene, alkylnaphthalene, isophorone, methyl isobutyl ketone, cyclohexanone, butyrolactone, cyclohexane, dimethyl Sub-milling, hydrazine, hydrazine-dimethylformamide, hydrazine, hydrazine-dimethylacetamide, hydrazine-methyl-2-pyrrolidinium, and alcohol; anionic surfactants, such as salts of fatty acids, Benzoate, alkyl sulfosuccinate, dialkyl sulfosuccinate, polycarboxylate, alkyl sulfate, alkyl sulfate, alkyl aryl sulfate, alkyl digan Alcohol ether sulfate, alcohol sulfate salt, alkyl sulfonate, alkyl aryl sulfonate, aryl sulfonate, lignosulfonate, alkyl diphenyl ether disulfonate, polystyrene a salt of a sulfonate, an alkyl phosphate, an alkyl aryl phosphate, a styryl aryl phosphate, a polyethylene oxide alkyl ether sulfate, Ethylene oxide alkyl aryl ether sulfate, polyethylene oxide alkyl aryl ether sulfate salt, polyethylene oxide alkyl ether phosphate, polyethylene oxide alkyl aryl phosphate Salt and naphthalene sulfonate and formaldehyde condensate; nonionic surfactant, such as sorbitan fatty acid ester, glycerin fatty acid ester, -26- 201029575 fatty acid polyglyceride, fatty acid alcohol polyglycol ether, acetylene glycol , alkylene oxide block polymer, polyethylene oxide alkyl ether, polyepoxy aryl ether, polyethylene oxide styryl aryl ether, polyethylene oxide ether, polyethylene Alcohol, polyethylene oxide fatty acid ester, polyepoxylated fatty acid ester, polyethylene oxide glycerin fatty acid ester, polycyclic hydrogenated castor oil and polypropylene oxide fatty acid ester; plant and mineral oil, Cross oil, kapok seed oil, castor oil, palm oil, camellia oil, coconut Φ sesame oil, corn oil, rice bran oil, peanut oil, cottonseed oil, soybean oil seed oil, linseed oil, tung oil, and liquid paraffin. The individual components of the agent may be one or more appropriately selected users as long as the object of the present invention is achieved. Further, the use of the aforementioned additional additives may be appropriately selected, some of which are known in the art. For example, various additives or adjuvants generally used, such as thickeners, anti-icing antifreezes, dispersion stabilizers, phytotoxicity reducing agents, antifungal agents, 'anti-sticking agents, lubricating adjuvants, desiccants, antioxidants, UV and so on. The weight of the compound of the present invention for various additives (including adjuvants) is usually 0.001:99.999 to 95:5, preferably 0.005:99.995 § 〇 In the practical application of the formulation, it may be in the original form' or may be used The diluent (such as water) is diluted to a predetermined concentration, and it is necessary to add various spreading agents such as a surfactant, or mineral oil thereto. Application of agricultural and horticultural insecticides containing the compound of the invention acetylene alcohol ethane alkanediol ethane oxalate such as olive oil, zhizhi, rapeseed can be added by means of a reducing agent, an antifoaming agent Dose ratio: 9〇: The use of visible vegetable oil cannot be determined by -27-201029575, as it varies depending on the climatic conditions, the type of formulation, the season of application, the site of application or the extent of insect outbreaks. 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 g, preferably from 1 to 30,000. g/ha. Further, as another preferred embodiment of the insecticide containing the compound of the present invention, agricultural and horticultural insecticides can be applied according to the aforementioned insecticide application. The present invention includes such a method of controlling pests, particularly for the treatment of plant parasitic mites, agronomic insect pests or plant parasitic nematodes by the application. The agricultural and horticultural insecticides containing the compounds of the present invention or diluted compositions thereof can be applied by conventionally applied methods such as spreading (for example, spreading, spraying, spraying, atomizing, powder or granule spreading or dispersion). In water), soil application (eg mixing or soaking), surface application (eg coating, dusting or covering) or impregnation to obtain toxic copper. 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. In addition, the active ingredient can also be applied by a so-called ultra low volume application method. In this method, the composition may consist of 100% active ingredient. Further, agricultural and horticultural insecticides containing the compound of the present invention may be used in combination or in combination with other agrochemical chemicals, fertilizers or phytotoxicity reducing agents, sometimes with synergistic effects or activities. Such other agrochemical chemicals include, for example, herbicides, insecticides, acaricides, nematicides, soil insecticides, fungicides, antivirals, attractants, antibiotics, plant hormones, plant growth regulators, and the like. . In particular, the use of a mixed insecticide which mixes or combines the compound of the present invention with an active compound of one or -28-201029575 of various other agrochemical chemicals can improve the application range, application time, insecticidal activity and the like in a preferred direction. The compounds of the invention and the active compounds of other agrochemical chemicals may 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 a mixed insecticidal composition. The mixing weight ratio of the compound of the present invention to the active compound of other agrochemical chemicals cannot be defined in a blanket manner because it varies depending on the climatic conditions, the type of formulation, the application time, the application site, the type or extent of the insect pest outbreak, and the like, However, it is usually in the range of 1:300 to 300:1 by weight, preferably 1:1000 to 10.0:1. Further, the dosage system is applied such that the total amount of the active compound is from 0.1 to 50,000 g, preferably from 1 to 30, g/ha. The present invention includes a method for controlling pests by applying the mixed insecticidal composition, an active compound of an insect pest controlling agent, such as an insecticide, acaricide, nematicide or soil in other agrochemical chemicals mentioned above. Insecticides, including φ (for example, using common names, some of which are still in the application stage, or test specifications), organophosphate compounds such as profenofos, dichlorvos, fenamiphos, and extinguishing Fenitrothion , EPN , diazinon , chlorpyrifos , chlorpyrifos-methyl , acephate , prothiofos , fosthiazate , sulphur Cadusafos, dis 1 ufot ο η, isoxathion, isofenphos, ethion, etrimfos, quetiapine ( 29- 201029575 quinalphos ), dimethylvinphos, dimethoate, suiprofos, methyl ethion Thiometone, vamidothion, pyraclofos, pyridaphthion, pirimiphos-methyl, propaphos, phosalone, hibiscus Forin〇thion), marathion, tetrachlorvinphos, chlorfenvinphos, cyanophos, trichlorfon, methidathion, phenthoate ), ESP, azinphos-methyl, fenthion, heptenophos, methoxychlor, parathion., phosphocarb, extinction Demeton-S-methyl, monocrotophos, methamidophos, imicacyfos, methyl balason, terbufos, phosphamidon , phosmet and phorate; urethane compounds such as carbaryl, propoxur, aldicarb, carbofuran, sulphur Enemy thiodicarb ), methomyl, oxamyl, ethiofencarb, pirimicarb 'fenobucarb, butyl plus carbosulfan, propyl thiophene Benfuracarb, bendiocarb, furathiocarb, isoprocarb, metolcarb, xylylcarb 201029575, XMC and fenothiocarb; Nereistoxin derivatives, such as cartap, thiocyclam, bensultap, and thiosultap-sodium; organochlorine compounds, such as dicofol, de- 蹒(tetradifon), endosulfan, dienochlor, and dieldrin: organometallic compounds such as fenbutatin oxide and cyhexatin; pyrethrum vinegar compounds, Such as fenvalerate, permethrin, cyp ermethr in, deltamethrin, cyhalothrin, tefluthrin, efenin ( ethofenprox ), Sancha Flufenprox, cyfluthrin, fenpropathrin, flucythrinate, fluvalinate, cycloprothrin, λ-cylonine (lambda-cyhalothrin), pyrethrins, esfenvalerate, tetramethrin, resmethrin, protrifenbute, bifenthine vinegar (bifenthrin), cypermethrin, cyrinathrin, a-% cypermethrin, allethrin Pyrethroid, tralomethrin, profluthrin, 5-cypermethrin, cyfluthrin, metofluthrin, phenothrin and cypermethrin (flumethrin); benzoquinone compounds, such as diflubenzuron, chlorfluazuron, flubenzuron (-31 - 201029575 teflubenzuron), flufenoxuron, triflumuron, fluoride Hexaflumuron, Lufenuron, novaluron, no vi flumuron, bistrifluron and fluazuron; juvenile hormones such as worms Methoprene, pyriproxyfen, fenoxycarb, and diofenolan; antimony compounds such as fenpyroximate, fipronil, 卩Tebufenpyrad, ethiprole, tolfenpyrad, acetoprole, pyrafluprole and pyriprole; neonicotinoids, such as Imidacloprid, nitenpyram, acetamiprid, thiacloprid, thiamethoxam, clothianidin, dinotefuran And nithiazine; 肼 compounds such as tebufenozide, methoxyfenozide, chromafenozide and hafenofozide; pyridoxine compounds such as Ether (pyridalyl) and Fonicamid; a tetronic acid compound such as spirodiclofen; a strobilurin compound such as fluacrypyrim; a pyrimidine compound such as fluorine Flufenerim: dinitro compounds; organic sulfur compounds; urea compounds; three-till compounds; antimony compounds; and other compounds such as buprofezin, hexythrone (hexythiazox), amitraz 201029575 Pyrethroids (inhibitors, mitmidonitrile (amitraz), chlordimeform silafluofen), triazamate pymetrozine, pyrimidi fen chlorfenapyr, indoxacarb ), acequinocyl, etoxazole, cyromazine, 1,3-dichloropropene, diafenthiuron, benclothiaz, biphenyl vinegar (bifenazate), spiromesifen, spirotetramat, propargite, clofentezine, metaflumizone, flubendiamide (fl Ubendiamide), cyflumetofen, chlorantraniliprole, cyenopyrafen, pyrifluquinazon, fenazaquin, pyrababen, sulphate Amidoflumet, chlorobenzoic acid vinegar, sulfluramid, hydramethylnon, meditation, HGW 86, ryanodine and verbutin. Further, for example, a microbial insecticide can be mentioned, such as Bacillus thuringiensis aizawai, kurstaki var. Bacillus thuringiensis kurstaki, Bacillus thuringiensis israelensis, Japan Manufactured from Bacillus thuringiensis japonensis, Bacillus thuringiensis tenebrionis or Bacillus thuringiensis, insect virus, etomopathogenic fungi and nematophagous fungi杀-33- 201029575 Insect crystalline protein; antibiotic or semi-synthetic antibiotics, such as avermectin, emamectin-benzoic acid vinegar, milbemectin, mibemycin ( Milbemycin, spinosad, ivermectin, lepimectin, DE-175, abamectin, emamectin and stibitre (spinetoram): natural products, such as azadirachtin and poisonous squid (r Otenone ); and repellents, such as deet.

The fungicidal active compounds in the aforementioned other agrochemical chemicals include, for example, (using common names, some of which are still in the application stage, or the test specifications of the Japan Plant Protection Association) aniline pyrimidine compounds such as mepanipyrim and pyramimethanil. ), cyprodinil and pyrimidine; trisicil, such as 5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4 , 6-trifluorophenyl) [1,2,4]triazolo[l,5-a]pyrimidine; pyridinamine compound, such as fluazinam; terpenoids, such as triadimefon , bittertanol, triflumizole, etaconazole, propiconazole, penconazole, flusilazole, myclobutanil ), cyproconazole, tebuconazole, hexaconazole, furfur 〇na ζ ο 1 e - cis, proch 1 〇raz, hydroxy Metconazole, epoxiconazole, strontium tetrahydrofluoride Traconazole ), oxpoconazole -34- 201029575 fumarate , sipconazole , prothioconazole , triadimenol , flutriafol , 啰Difenoconazole, fluquinconazole, fenbuconazole, bromuconazole, diniconazole, tricyclazole, probenazole, Simeconazole, pefurazoate, ipconazole, and imibenconazole; quinoline compounds, such as quinomethionate; dithiocarbamate compounds, Such as maneb, manzine, mancozeb, urethane, metiram, propineb and thiram; Organochlorine compounds such as fthalide, chlorothalonil and quintozene; imipenem compounds such as benomyl, thiophanate- Methy l), carbendazim, thiabendazole, fuberiazole and cyazofamid; cyanoacetic acid amine compounds, such as cymoxanil: phenylguanamine compounds Such as metalaxyl, metalaxyl-M, mefenoxam, oxadixyl, ofurace, benaxyl, Benalaxyl-M (another name: kiralaxyl, chiralaxyl), furalaxyl and cyprofuram; sulfenic acid compounds such as diflulofluanid; copper compounds such as Hydrogen-35- 201029575 Copper oxide and copper hydroxyparaphyllin; isoxazole compounds such as carbendazim; organophosphorus compounds such as triethylphosphonic acid-A1, tolclofos-methyl, edifenphos , iprobenfos, hydrazine, hydrazine-diisopropyl-thiophosphoric acid S-benzyl ester, S, S-diphenyl thiophosphate 0-ethyl ester and ethyl hydrogen phosphinate; N- Halothioalkyl compounds such as captan, captafol and folpet; Indoleamine compounds, such as procymidone, iprodione, and vinclozolin; phenyl anilide compounds such as flutolanil and mepronil ), zoxamid and tiadinil; aniline compounds such as carboxin, oxycarboxin, thifluzamide, penthiopyrad ), boscal id, isothianil, bixafen, and two syngeneic isomers 3-(difluoromethyl)-1-methyl-N -[ ( 1RS,4SR,9RS ) -1,2,3,4-tetrahydro-9-isopropyl-1,4-methylnaphthalen-5-yl]pyrazole-4-carboxamide and 2 The isomer 3-(difluoromethyl)-bumethyl-:^-[(1«^,4811,9811)-1,2,3,4-tetrahydro-9-isopropyl-1,4 Mixture of -methylnaphthalen-5-yl]pyrazole-4-carboxamide (isopyrazam): piperidine compound, such as triforine: pyridyl compound, such as pyrefenox •, primary alcohol Compounds such as fenarimol and flutriafol: pipe steep a compound such as fenpropidine; a morpholine compound such as fenpropimorph, spiroxamine, and tridemorph; organotinated 201029575 compound, such as hydroxide III Phentin hydr〇xide and triphenyltin acetate; urea compounds such as Pencycuron; cinnamic acid compounds such as dimethomorPh and flumorph: phenylamine Carbamate compounds, such as diethofencarb: cyanopyrrole compounds, such as fludioxonil and fenpiclonil; strobilurin compounds, such as azoxystrobin ), kresoxim-methyl, metomino fen, trifloxystrobin, picoxystrobin, oryzastrobin, dimoxystrobin, Pyraclostrobin and fluoxastrobin; chewing ketone compounds such as famotoxadone; thiazolidine compounds such as ethaboxam: 矽a base amine compound such as silthiopham; an amino acid amide amine urethane compound such as iprovalicarb, benthiavalicarb-isopropyl and 1^ -(isopropoxycarbyl)-1^ amidoxime-(3118)-3-(4-chlorophenyl)-/8-alanine methyl ester (valifenalate); imidazolium compound, such as imidacloprid (fenamidone); a hydroxyaniline compound such as fenhexamid: a benzenesulfonamide compound such as flusulfamide; an oxime ether compound such as cyflufenamid; phenoxy amide Compounds such as fenoxanil; antibiotics such as vaiidamycin, kasugamycin and polyoxomycin; bismuth compounds such as gram-37-201029575 iminoctadine and many more Dodine; a quinoline compound such as 6-t-butyl-8-fluoro-2,3-dimethylquinolin-4-yl acetate (tebufloquin); a thiazolidine compound such as 2-[2 -fluoro-5-(trifluoromethyl)phenylthio]-2-[3-(2-methoxyphenyl)thiazolidin-2-ylidene]acetonitrile (f Lutianil ); and other compounds, such as isoprothiolane, pyroquilon, diclomezine, quinoxyfen, propamocarb hydrochloride, chloropicrin Chloropicrin ), dazomet chlorate (metam-sodium), nicobifen, metrafenone, MTF-753, UBF-307, chloramphenicol ( Diclocymet), proquinazid, amisulbrom ' pyribencarb , mandipropamid , fluopicolide , cyproterone Carpropamid, meptylidinocap, floopyram, BCF-051 'BCM-061 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, ectoparasites that are parasitic on the surface of the host animal (such as the back, armpits, lower abdomen or inner thigh) or parasitic in the host animal (such as the stomach, intestines, lungs, Endoparasites of the heart, liver, blood vessels, subcutaneous tissue or lymphoid tissue - 38- 201029575, 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 different types that it is difficult to fully list them, so list their typical examples.

The animal parasitic hair follicle may be, for example, a ticks such as Boophilus microplus, Rhipicephalus sanguineus, Haemaphysalis longicornis, Haemaphysalis flava, short-sleeved blood clams. (Haemaphysalis campanulata), Haemaphysalis concinna, Haemaphysalis japonica, Haemaphysalis kitaokai, Haemaphysalis ias, Ixodes ovatus, Japanese hard palate (Ixodes) Nipponensis ), Ixodes persulcatus, Amblyomma testudinarium, Haemaphysalis megaspinosa, Dermacentor reticulatus, and Dermacentor taiwanesis; red for J Spider (Dermanyssus gallinae): northern fowl mite, such as Ornithonyssus syl viarum and tropical bird contact (Ornithony s sus bursa); trombiculidae, such as Eutrobicula wichmanni, red Fibrous touch

Leptotrombidium akamushi ) , Leptotrombidium pallidum , Leptotrombidium fuj i , Leptotrombidium to sa Autumn ( Neotrombicula autumnalis ) ' North American 恙 螨 ( -39- 201029575

Eutrombicula alfreddugesi and Helenicula miyagawai; carnivora, such as Cheyletiella yasguri, Cheyletiella p aras iti vorax and Cheyletiella blakei; sarcoptic mange mite, such as Psoroptes Cuniculi), Chorioptes bovis, Otodectes cynotis, Sarcoptes scabiei, and Notoedres cati; and Demodicidae, such as dogs Demodex canis. The insecticide containing the compound of the present invention against parasitic animals is particularly effective in controlling (especially) tick. The steroids may, for example, be in vitro parasitic insects belonging to the genus Siphon aptera, especially those belonging to the genus Pulicidae, Ceratephyllus and the like. The genus belonging to the genus Aphididae can be, for example, Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Echidnophaga gallinacea, Xenopsylla cheopis, and Leptopsylla. Segnis), European squid (Nosopsyllus fasciatus) and unequal scorpion (Monopsyllus anisus). The insecticide containing the compound of the present invention against parasites in animals is particularly effective for controlling the species belonging to the family Aphididae, among which Ctenocephalides canis and Ctenocephalides felis. Other ectoparasites may, for example, be Anoplura, such as Haematopinus eurysternus, Haematopinus asini, Sheep, and Proboscis (Linognathus 201029575).

Vituli) and Pediculus capitis; ticks, such as Trichodectes canis; and blood-sucking dipterous insects, such as Tabanus trigonus, Culicoides schultzei, and Simulium ornatum ). Further, the endoparasite may 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, Dipylidiuna caninum, Taenia multiceps, Echinococcus granulosus, and Echinococcus multilocul aris; Trematoda, such as Schistosoma japonicum and Fasciola hepatica; and protozoa, such as coccidia, Plasmodium malariae, intestinal spores 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 rhyme, a crane, a crane, a Javanese, a honey crane). Crane (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 pet animals or livestock. -41 - 201029575

When the compound of the present invention is used as an insecticide against parasites in animals, 'can be used in its original state or can be used together with appropriate additives to prepare various formulations such as powders, granules, powder granules, tablets , microcapsules, soluble concentrates, emulsifiable concentrates, oil solutions, water-soluble powders, water-soluble granules, water-based suspension concentrates, oil-based suspension concentrates, wettable powders, water-dispersible Granules, pastes and smoked insecticides. 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 additive to be used in the formulation may, for example, be an anionic surfactant or a nonionic surfactant exemplified as an additive when used in the formulation of agricultural and horticultural insecticides; a cationic surfactant such as hexabromide Alkyltrimethylammonium: solvent such as water, hydrazine, hydrazine-dimethylacetamide 'N,N-dimethylformamide, N-methyl-2-pyrrolidone, cyclohexanone, iso Propanol,

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 n-butyl ether, dipropylene glycol monomethyl ether or dipropylene glycol n-butyl ether; antioxidants such as butyl hydroxy anisole, butyl hydroxy toluene, ascorbic acid, sodium metabisulfite, no food Propyl acrylate or sodium thiosulfate; coating film forming agent, such as polyvinylpyrrolidone, polyvinyl alcohol or a copolymer of vinyl acetate and vinyl pyrrolidone; vegetable oil and mineral oil, as previously described for agricultural use and Additives exemplified by the formulation of horticultural insecticides: carrier, such as lactose, sucrose, glucose, starch, flour, clay, bentonite, talc, diatomaceous earth, calcium carbonate, white carbon, sodium sulfate, ammonium sulfate, urea; Wait. One or more of these additives may be appropriately selected and used as long as the use does not deviate from the object of the present invention. Further, some of those known in the art may be appropriately selected and used in addition to the aforementioned additives, and some of the aforementioned various additives 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 additives 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 with various spreading agents (eg, φ surfactant, Vegetable oil 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 lozenge, a liquid medicament, a capsule, a tablet, a medicated cake, 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 applied to the surface φ of the body 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 dose ratio is 0.01 mg to 100 g, preferably 0.1 mg to 10 g π kg of the host animal body weight. 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 can be prevented or treated in some cases. 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, sedatives, anti-inflammatory agents may be blended or combined with the additives. , fungicides, colorants, aromatic substances, preservatives, etc. In addition, other animal drugs or agrochemicals such as vitamins, anthelmintics, coccidiostats, insecticides, acaricides, miticides, nematicides, or antibacterial agents may be mixed as the case may be. Or combined use, sometimes improved results can be obtained. The present invention includes a mixed insecticidal composition in which the above various components are mixed or used in combination, and a method for controlling pests by using the composition, particularly a method for controlling ectoparasites or endoparasites. A preferred embodiment of the compound of formula (I) is a triazolopyrimidine derivative wherein, in formula (I), R1 is an alkyl group which may be substituted by A, a cycloalkyl group which may be substituted by A, a halogen , cyano, S(0)nR3 or NR3R4 or a salt thereof. However, the invention is by no means limited thereby. [Embodiment] Now, the embodiments of the present invention are described, but it should be understood that the present invention is by no means limited thereto. First, synthetic examples of the compounds of the present invention are described. -44 - 201029575 Preparation Example 1 5-methyl-7-(4-(trifluoromethyl)pyrimidin-2-yl)-[1,2,4]triazolo[l,5-a]pyrimidine ( Preparation of Compound No. 8) (1) wherein 470 mg of 2-ethylindenyl-4-trifluoromethylpyrimidine and 1 ml of hydrazine, dimethyl-dimethylacetamide dimethyl acetal are dissolved in 10 ml of toluene The solution was stirred under hot reflux for 5 hours. After the reaction was terminated, the φ solvent was distilled off under reduced pressure to give (Ε)-3-dimethylamino 1-(4-(trifluoromethyl)pyrimidin-2-yl)-2-butene-b. Ketone liquid. (2) Add 10 ml of acetic acid and 229 mg of 3-amino-1Η-1,2,4-triazole to all (())-3-dimethylamino-1-(#) obtained in (1) In a liquid of 4-(trifluoromethyl)pyrimidin-2-yl)-2-buten-1-one, the mixture was stirred at 100 ° C for 2 hours. After the reaction was terminated, the solvent was distilled off under reduced pressure to give water. It was added to the obtained residue, and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate, dried over anhydrous sodium sulfate and evaporated. The residue was purified by EtOAc EtOAc (EtOAc:EtOAc) PREPARATIVE EXAMPLE 2 5_Cyclopropyl-7-(1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)-[1,2,4]triazolo[1, Preparation of 5-a]pyrimidine (Compound No. 3) (1) Add 161 mg of sodium ethoxide to 350 mg of 1-methyl-3-(trifluoromethyl)-1Η-pyrazole at about 60 ° C with stirring. In a mixture of -5-ethyl formate, 400 mg of cyclopropylmethyl ketone and 3.5 ml of anhydrous tetrahydrofuran - 45 - 201029575, after the addition was terminated, the resulting solution was stirred at the same temperature for 50 minutes. After the reaction was terminated, the reaction mixture was cooled to room temperature, and 1N hydrochloric acid was added to the reaction mixture to make it acidic, and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution and dried over anhydrous sodium sulfate, and then evaporated under reduced pressure. The residue obtained was purified by EtOAc EtOAc (EtOAc:EtOAc:EtOAc Methyl)-1H-pyrazol-5-yl)propane-1,3-dione. The NMR spectrum of the obtained product is shown below. 1H-NMR <5 ppm (solvent: CDC13 /400MHz) 1.03 (m, 2H), 1.24 (m, 2H), 1.70 (m, 1 Η ), 4 · 2 3 ( s, 3 Η ), 6.09 ( s,lH ), 6.92 ( s,3H ) (2 ) 5 ml of acetic acid and 1 18 mg of 3-amino-1H-1,2,4-triazole were added to 181 mg of 1-cyclopropyl-3 -(1-Methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)propane-1,3-dione, the mixture was stirred at reflux for 3 hours, then 118 mg of 3-amino group -1H-1,2,4-triazole was added to the mixture, followed by stirring under hot reflux for 24 hours. After the reaction was terminated, the reaction mixture was cooled to room temperature, and water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium hydrogen sulfate and brine and dried over anhydrous sodium sulfate. The residue obtained was purified by EtOAc EtOAc (EtOAc:EtOAc) A typical example of a compound of formula (I) is shown in Table 1. In Table 1, the numbers represent the compound numbers, Me is a methyl group, Et is an ethyl group, i-Pr is an isopropyl group, and Ph is a phenyl group, and the temperature expressed in a physical form is a melting point. -46- 201029575 These compounds can be synthesized based on the various processes of Synthesis Examples 1 and 2 or the compounds of the present invention.

Table 1 N / R1 No. R1 Het Physical Properties Et 1 - <] 141-143 ° C Me 2 Me cf3 162-163 ° C 3 > 3 170-173 ° C 4 - <] Cl 156-157 ° C 5 Cl 177-178. . 6 Me Cl 175-176°C 7 Me N^i / person f3 101-105°C 8 Me ΛχΗ 149-153°C cf3 9 Me 82-85°C 10 Me j^y〇F3 211-215°C - 47- 201029575

Table 1 (continued)

No. R1 Het Physical Properties 11 -<] Me Me 115-118°C 12 -nh2 13 -NHCOMe 14 -NHCOCFg >F3 15 -ΝΜθ2 >F3 16 -NHMe 17 -CH(OMe)2 >F3 18 19 20 j^rCF3 Cl 21 Ph cf3 22 Me m>f3 122-124°C -48- 201029575

Table ι (continued) No. R1 Het Physical Properties 23 i-Pr N^n cf3 121-123°C 24 ·-<] Me /^-CF3 C! 124-125°C 25 cf3 N into NY^c, 26 Y^Me 191-193°C 27 ·-〇Me^N^ 28 ·—〇Me^N, ^Me 123-124°C 29 F3Cyn1 NV-Me 30 F3c>^Me 31 F>C1 -49- 201029575

Table ι (continued) No. R1 Het Physical Properties 32 A 33 34 J^Me 35 f3c^^ 36 -<l >^~Me Me' 37 -<] Me, NN 38 Me Ph 39 -<] Me . c \}-Me 40 Me S]i~Me 187°C 41 Me j^Me 148°C

-50- 201029575

Table ι (continued) No. R1 Het Physical properties 42 Me JlJ~CFz 153-154°C 43 Me Me 44 Me Me ύ- 45 Me cr 46 Me Cl 47 Et 48 i-Pr > F3 49 Br 50 201-208. . 51 Me 52 -0 i-Pr c,^CF3 149-150°C -51 - 201029575

Table ι (continued) No. R1 Het Physical Properties 53 Me, NN EtO-^^CFa 144-149°C 54 -<] cf3 146-150°C 55 Me Minute 1 Cl 114°C 56 —C] Et 90- 92°C 57 Me •VN7 〇Λ'Ν Me 139-140°C 58 Me Br>^Me 142°C 59 Me c^Me 184°C 60 Me dc 172°C 61 Me ON 156°C 62 -< Me $ 140-142°C 63 Me 124°C -52- 201029575

Table ι (continued) No. R1 Het Physical Properties 64 Me jS~a hf2c 165-167°C 65 Me NT0, JL/-cF3 92-94°C 66 -<l N〆0, JL/~CF3 112-114 °C 67 Me 丫Νγ〇Η N'^Me 275°C (decomposition) 68 Me .A 120-123°C 69 Cl 70 cf3 Λ Cl 71 Me n^VCF3 •v Cl r*VCF3 72 ^<3 Br 73 Me' ψα 171-173°C Now, a test case will be described. Test Example 1 -53 - 201029575 Test against the control effect of Myzus persicae (Myzuspersicae) The radish leaves were inserted into a test tube containing water, and about 20 green peach nymphs were released on the leaves. The next day' counts the number of nymphs parasitic on the leaves, after which the leaves are immersed in an insecticide solution adjusted to a concentration of 200 ppm of the compound of the invention for about 10 seconds, dried in air and left at 25 ° C under illumination. In the incubator. The number of dead nymphs was counted 5 days after the treatment, and the mortality was calculated by the following formula. An insect that has fallen from a leaf or exhibits a poisonous condition is considered an insect of death. Tests were carried out using the aforementioned compound numbers 3, 4, 24, 54 and 68, and all compounds showed a mortality rate of at least 90%. Mortality (%) = (1 - number of surviving insects / number of treated insects) xl 〇〇 test example 2 Test against the control effect of Nilaparvatalugens Seedlings were adjusted to a concentration of 200 ppm of the compound of the present invention Soaking in the insecticide solution for 10 seconds', then drying in the air, the roots are covered with absorbent cotton, and the seedlings are placed in a test tube. Thereafter, the second to third instar nymphs of the cockroach are released into the tube. The gauze covers the test tube's and is placed in an incubator under illumination at 25 ° C. After the release, the number of dead nymphs is counted, and the mortality is calculated by the following formula. For the aforementioned compound numbers 1, 3, 4, 5 6, 24' 26, 28, 50, 54, 57, 62, 66, 68 and 73 were tested and all compounds showed at least 90% mortality. Mortality (%) = (number of dead insects / release) Insect number) X100 -54- 201029575 Test Example 3 Test for the control effect against white powder 13⁄4 (Bemisia argentifolii) The insecticide solution adjusted to a concentration of 200 ppm of the compound of the present invention by manual spraying was applied to the parasitic white powder one to two. Yellow in the nymph of the nymph The melon seedlings are dried in the air. After that, the cucumber seedlings are left in an incubator under the φ light at 25 ° C. The nymphs are counted on the 10th day after the treatment, and the protection 値 (%) is obtained by the following formula. Compound Nos. 3, 4, 22, 24, 26, 28, 50, 54, 65, 66 and 68 were tested and all compounds showed at least 80% mortality. Protection 値 (%) = (1-( TaxCb / ( TbxCa) ) ) xlOO Ta: Number of old nymphs at treated cucumber seedlings after treatment Tb: Number of nymphs from one to two in the treated cucumber seedlings before treatment Ca: untreated cucumber after treatment Number of nymphs at the seedlings φ Cb: Number of nymphs of the first to second instars at the untreated cucumber seedlings before treatment. Test Example 4 The insecticide test using the dog against Haemaphysalis longicornis will contain a dose of 10 A gelatin capsule of the compound of the invention in milligrams per kilogram weight is applied to a dog (Beagle, 8 months old), and about 50 young cerevisiae of Haemaphysalis longicornis are placed in the dog immediately after administration - 55- 201029575 Artificial parasitism on the auricle. After treatment, proceed Observing the number of parasites, the number of falls, and the mortality of falling long-horned blood stasis. As a result, the compound of the present invention can effectively cause parasitic long-horned blood stasis to fall or die. Test Example 5 Using a dog to fight against cat mites (Ctenocephalides felis) Insecticide test A gelatin capsule containing a compound of the invention at a dose of 10 mg/kg is applied to a dog (Beagle, 8 months old), and about 1 非 of non-hemorrhagic feline mites are released from the back immediately after administration. Artificial and parasitic on the hair. The compounds of the present invention show an inhibitory effect on the hatching of the eggs produced by the treated adults. Now, the formulation examples are described below. Formulation Example 1 2 parts by weight 7 parts by weight 5 parts by weight 3 parts by weight 2 parts by weight (1) Compound of the invention (2) Clay (3) White carbon (4) Sodium polycarboxylate ( 5) Sodium alkylnaphthalenesulfonate The above components were uniformly mixed and pulverized to obtain a wettable powder. Formulation Example 2 -56- 201029575 5 parts by weight 60 parts by weight 34.5 parts by weight 0.5 parts by weight (1) Compound of the invention (2) Clay (3) Calcium carbonate (4) Liquid paraffin The above components are homogeneous Mix to obtain a powder. Formulation Example 3 (1) 20 parts by weight of the compound of the present invention (2) 20 parts by weight of N,N-dimethylacetamide (3) 10 parts by weight of polyethylene oxide tristyrylphenyl ether Number (4) 2 parts by weight of calcium dodecylbenzenesulfonate (5) 48 parts by weight of xylene The above components were uniformly mixed and dissolved to obtain an emulsifiable concentrate. Formulation Example 4 φ (1) Clay 68 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 the compound of the present invention at a weight ratio of 4:1 and pulverized to obtain a wettable powder. Formulation Example 5 -57- 201029575 (1) Compound of the present invention 50 parts by weight (2) Condensate of sodium alkylnaphthalenesulfonate and formaldehyde 2 weight &# (3) Polyoxyxylene oil 0.2 parts by weight Number (4) Water 47.8 parts by weight The above components were uniformly mixed and pulverized to obtain a matrix liquid 'and (5) sodium polycarboxylate 5 parts by weight (6) anhydrous sodium sulfate 42.8 parts by weight of the mixture Uniformly mixed, granulated and dried to obtain water-dispersible granules 5 parts by weight 1 part by weight 0.1 parts by weight 93.9 parts by weight of the formulation Example 6 (1) The compound of the invention (2) Polyethylene oxide Octyl phenyl ether (3) Polyethylene oxide alkyl ether phosphate (4) Granular calcium carbonate ❹ The above components (1) to (3) are uniformly mixed in advance, diluted with an appropriate amount of acetone, and then the mixture is sprayed. On component (4), acetone was removed to give granules. 2.5 parts by weight 2.5 parts by weight 9 5.0 parts by weight An ultra-low volume formulation was obtained. Formulation Example 7 (1) Compound of the present invention (2) N,N-dimethylacetamide (3) seed oil methyl ester The above components were uniformly mixed and dissolved -58-201029575 Formulation Example 8 ( 1) 40 parts by weight of the compound of the present invention (2) Polyethylene oxide tristyrylphenyl ether potassium phosphate 4 parts by weight 0.2 parts by weight 0.1 parts by weight 5 parts by weight 50.7 parts by weight (3) Poly Sand oil (4) Hansheng gum (5) Ethylene glycol (6) water The above components are uniformly mixed and pulverized to obtain a water-based suspension concentrate. Formulation Example 9 (1) Compound of the present invention 10 parts by weight (2) Diethylene glycol monoethyl ether 80 parts by weight 10 parts by weight (3) Polyethylene oxide alkyl ether

The foregoing components were uniformly mixed to give a soluble concentrate. Formulation Example 1 〇 (1) 40 parts by weight of the compound of the present invention (2) 5 parts by weight of a condensate of sodium alkylnaphthalene sulfonate and formaldehyde (3) 1 part by weight of sodium dioctyl sulfosuccinate ( 4) 54 parts by weight of lactose The above components were uniformly mixed and pulverized, followed by adding water and mixing. The mixture was granulated, dried and surface-treated to obtain water-soluble granules. The entire disclosure of the Japanese Patent Application No. 2009-017716, filed on Jan. 29, 2009, which is hereby incorporated by reference in its entirety, in

-60-

Claims (1)

201029575 VII. Patent application scope: A triazolopyrimidine derivative represented by formula (I) or a salt thereof: Het (I) wherein R 1 is an alkyl group which may be substituted by A, a cycloalkyl group which may be substituted by a, an alkenyl group which may be substituted by A, an alkynyl group which may be substituted by A, a halogen, a cyano group, an aryl group, 1 , 3-dioxolyl, COR2, S(O) nR3, NR3R4 or c〇NR3R4; Het is A is halogen, OR2, alkyl or cycloalkyl; R2 is hydrogen, alkyl, haloalkyl, alkoxy or NR3R4; R3 is hydrogen or alkyl; R4 is hydrogen, alkyl, halo Alkyl, alkylcarbonyl, alkoxycarbonyl, haloalkylcarbonyl or haloalkoxycarbonyl; X is alkyl, alkenyl, alkynyl, aryl, halogen, haloalkyl, cyano, nitro, NR3R4 , S ( Ο ) nR3, OR2 or COR2; Y is oxygen, sulfur or NR5; R5 is alkyl, haloalkyl, cycloalkyl or aryl; η is an integer from 0 to 2; w1 is 1 An integer from 3 to 2; w2 is an integer from 1 to 2; and when the condition is w1 or w2 is at least 2' -61 - 201029575 plural χ may be the same or different, with the restriction that the following cases are excluded: (1) R1 is a methyl group, and Het is a 5-hydroxy-3-methyl-1-phenyl-pyrazol-4-yl' (2) R1 is a phenyl group, and Het is a 1-ethyl-pyridyl group. Zyridin-4-yl, (3) R1 is methyl, Het is alkyl substituted thiophen-2-yl, and (4) R1 is trifluoromethyl, and Het is substituted by alkyl Thiophen-2-yl. 2. The triazolopyrimidine derivative or a salt thereof according to claim 1, wherein R1 is an alkyl group which may be substituted by A, a cycloalkyl group which may be substituted by A, or a halogen 'cyano' S (Ο) nR3 or NR3R4. 3. An insecticide comprising a triazolopyrimidine derivative or a salt thereof as defined in the first paragraph of the patent application as an active ingredient. 4. An agricultural and horticultural insecticide comprising a triazolopyrimidine derivative or a salt thereof as defined in the scope of claim 1 as an active ingredient. An insecticide, a sterilizing agent, a nematicide or a soil insecticide, which comprises the triazolopyrimidine derivative or a salt thereof as defined in the first aspect of the patent application as an active ingredient. An insecticide or acaricide containing a triazolopyrimidine derivative or a salt thereof as defined in the first aspect of the patent application as an active ingredient. 7. A method for controlling pests, which comprises applying an effective amount of a triazolopyrimidine derivative or a salt thereof as defined in claim 1 of the patent application, and producing a triterpenoid represented by formula (I) Method for pyrimidine derivatives or salts thereof: -62- 201029575 Het (I) wherein R 1 is an alkyl group which may be substituted by A, a cycloalkyl group which may be substituted by A, an alkenyl group which may be substituted by A, an alkynyl group which may be substituted by A, a halogen, a cyano group, an aryl group, 1 , 3-dioxolyl, COR2, S(O) nR3, NR3R4 or CONR3R4; Het is A is halogen, OR2, alkyl or cycloalkyl; R2 is hydrogen, alkyl ©, haloalkyl, alkoxy or NR3R4; R3 is hydrogen or alkyl; R4 is hydrogen, alkyl, halogen An alkyl group, an alkylcarbonyl group, an alkoxycarbonyl group, a haloalkylcarbonyl group or a haloalkoxycarbonyl group; the X system is an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a halogen, a haloalkyl group, a cyano group, a nitro group, NR3R4, S(O)nR3, OR2 or COR2; Y is oxygen, sulfur or NR5; R5 is alkyl, haloalkyl, cycloalkyl or aryl; η is an integer from 0 to 2; w1 is An integer from 1 to 3; w2 is an integer from 1 to 2; and when the condition is w1 or w2 is at least 2, X may be the same or different, with the constraint that the following is excluded: (1) R1 is methyl And Het is 5-hydroxy-3-methyl-1-phenyl-pyrazol-4-yl-63-201029575, (2) R1 is phenyl, and Het is 1-ethyl-pyrazole -4-yl, (3)Ri is methyl, and Het is alkyl substituted thiophen-2-yl, and (4) R1 is trifluoromethyl, and Het is substituted by alkyl Thiophen-2-yl This method comprises (1) an α,/3-unsaturated ketone derivative represented by the following formula (IV): Het R7 N^r7 wherein Rla is an alkyl group which may be substituted by A1, a cycloalkyl group which may be substituted by A1, an alkenyl group which may be substituted by A1, an alkynyl group or an aryl group which may be substituted by A1; and A1 is OR2a , alkyl or cycloalkyl; R 2a is hydrogen, alkyl or haloalkyl; R 7 is alkyl; and Het is condensed as defined above with a compound of formula (V), NH 2 (V) image 2) a cr,yS-unsaturated ketone derivative represented by the formula (VII): Het SR33 (W) wherein R3i> is an alkyl group; and Het is as defined above, and a compound represented by the formula (V) Condensation, (3) oxidation of the compound of formula (1-2): -64- 201029575 (1-2) wherein Het and 1133 are as defined above, and (4) the compound of formula (1-3) is: (Ι·3) Or 2 of which Het and 1133 are as defined above; and na is a number, reacts with a nucleophilic reagent, (5) gives a compound of formula (IX): Het R1c (K) Wherein Rle is an alkyl group which may be substituted by hydrazine 1, an alkenyl group which may be substituted by A1, an alkenyl group which may be substituted by A1, an alkynyl group which may be substituted by A1: and A1 and Het are as defined above, and formula (V) The combination shown, or (6) the triazolopyrimidine derivative R1d (XIV) represented by the formula (χΙν) wherein Rld is an alkyl group which may be substituted by A, and may be substituted by A by a group An alkenyl group, an alkynyl group which may be substituted by a, Q1 is a halogen; and A is as defined above, a cycloalkane or an aryl group substituted with a ring of the formula (XV) or an aryl compound; : Het-B (-65-201029575 R13) a compound represented by p, wherein R13 is OH, alkyl, cycloalkyl, alkoxy or fluoro; when R13 is OH, alkyl, cycloalkyl or alkoxy, p is 2; when R13 is fluorine, P is 3; the alkyl or alkoxy group of R13 may be bonded to each other together with adjacent boron atoms to form a ring; and Het is as defined above. 201029575 IV. Designated representative map: (1) The representative representative of the case is: None (2) The symbol of the representative figure is simple: No -3- 201029575 V. If there is a chemical formula in this case, please reveal the chemical formula that best shows the characteristics of the invention: Formula (I) R1 N N Het (I)