WO2010087294A1

WO2010087294A1 - Triazolopyrimidine derivative or its salt, process for producing the same and pesticide containing the same

Info

Publication number: WO2010087294A1
Application number: PCT/JP2010/050863
Authority: WO
Inventors: Hirohiko Kimura; Toshihiko Ueki; Kazuhisa Kiriyama; Tomohiro Okamoto
Original assignee: Ishihara Sangyo Kaisha, Ltd.
Priority date: 2009-01-29
Filing date: 2010-01-19
Publication date: 2010-08-05
Also published as: JP2010195771A; TW201029575A; AR075046A1

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

DESCRIPTION

TRIAZOLOPYRIMIDINE DERIVATIVE OR ITS SALT, PROCESS FOR PRODUCING THE SAME AND PESTICIDE CONTAINING THE SAME

TECHNICAL FIELD

The present invention relates to a pesticide containing a novel triazolopyrimidine derivative or its salt as an active ingredient.

BACKGROUND ART Patent Document 1 discloses that a specific 7-heteroaryl [1 ,2,4] triazolo [1 ,5-a] pyrimidine can be used as a medicine. However, the compound of the present invention is not specifically described in Patent Document 1. Patent Document 2 discloses a pesticide 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, since in Patent Document 2, an Het part in the after-mentioned formula (I) is pyridyl.

Patent Document 1 : US Patent No. 4,444,774 Patent Document 2: WO2008/099902

DISCLOSURE OF THE INVENTION

OBJECT TO BE ACCOMPLISHED BY THE INVENTION

For many years, many pesticides have been used, but many of them have various problems such that the effects are inadequate, their use is restricted as pests have acquired resistance, etc. Accordingly, it is desired to develop a novel pesticide substantially free from such problems, for example, a pesticide capable of controlling various pests which create problems in agricultural and horticultural fields or a pesticide capable of controlling pests parasitic on animals.

MEANS TO ACCOMPLISH THE OBJECT The present inventors have conducted various studies on triazolopyrimidine derivatives in an effort to find a superior pesticide. As a result, they have found that a novel triazolopyrimidine derivative has an extremly high pesticidal effect against pests at a low does and safety on crops, natural enemies agains pests or mammals. Thus, the present invention has been accomplished . That is, the present invention relates to a pesticide containing, as an active ingredient, a triazolopyrimidine derivative represented by the formula (I) or its salt:

wherein R¹ is alkyl which may be substituted by A, cycloalkyl which may be substituted by A, alkenyl which may be substituted by A, alkynyl which may be substituted by A, halogen, cyano, aryl, 1 ,3-dioxolanyl, COR², S(O)_nR³, NR³R⁴ or CONR³R⁴; Het is

Het1 Het2 Het3 Het4

Het5 Het6 Het7

A is halogen, OR², alkyl or cycloalkyl; R² is hydrogen, alkyl, haloalkyl, alkoxy or NR³R⁴; R³ is hydrogen or alkyl; R⁴ is hydrogen, alkyl, haloalkyl, alkylcarbonyl, alkoxycarbonyl, haloalkylcarbonyl or haloalkoxycarbonyl; X is alkyl, alkenyl, alkynyl, aryl, halogen, haloalkyl, cyano, nitro, NR³R⁴, S(O)_nR³, OR² or COR²; Y is oxygen, sulfur or NR⁵; R⁵ is alkyl, haloalkyl, cycloalkyl or aryl; n is an integer of from 0 to 2; w¹ is an integer of from 1 to 3; w² is an integer of from 1 to 2; and in a case where w¹ or w² is at least 2, a plurality of X may be the same or different, 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.

EFFECTS OF THE INVENTION A pesticide containing the triazolopyrimidine derivative of the above formula (I) or its salt as an active ingredient has a very high pesticidal 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 in the case of at least 2, the substituents may be the same or different. Further, the position for substitution of each of X or A may be any position.

As the halogen in the formula (I), an atom of fluorine, chlorine, bromine or iodine may be mentioned. The number of halogen atoms as substituents may be 1 or at least 2, and in the case of at least 2, the respective halogen atoms may be the same or different. Further, the position for substitution of each halogen atom may be any position.

In the formula (I), the alkyl may be linear or branched. As a specific example of the alkyl, Ci_-6 alkyl such as methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl or hexyl may be mentioned.

In the formula (I), as the cycloalkyl, C₃-6 cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl may be mentioned.

In the formula (I), the alkenyl may be linear or branched. As a specific example of the alkenyl, C_∑-β alkenyl such as vinyl, 1-propenyl, allyl, isopropenyl, 1- butenyl, 1 ,3-butadienyl or 1 -hexenyl may be mentioned.

In the formula (I), the alkynyl may be linear or branched. As a specific example of the alkynyl, C2-6 alkynyl such as ethynyl, 2-butynyl, 2-pentynyl, 3-methy!-1- butynyl, 2-penten-4-ynyl or 3-hexynyl may be mentioned. In the formula (I), as the aryl, Cβ-io aryl such as phenyl or naphthyl may be mentioned.

The salt of the triazolopyrimidine derivative of the formula (I) includes all kinds so long as they are acceptable in this technical field. For example, an ammonium salt such as a dimethylammonium salt or a trimethylammonium salt; an inorganic acid salt such as a hydrochloride, a perchlorate, a sulfate or a nitrate; or an organic acid salt such as an acetate or a methane sulfonate may be mentioned.

The triazolopyrimidine derivative of the formula (I) may have some isomers such as optical isomers or geometrical isomers, and such isomers and mixtures of such isomers are both included in the present invention. In the present specification, isomers are described as a mixture unless otherwise specified. Further, in the present invention, various isomers other than those mentioned above, may be included within the scope of the common knowledge in this technical field. Further, depending on types of isomers, they may have chemical structures different from the formula (I), however, those skilled in the art can sufficiently recognize that such compounds are isomers of the compound of the present invention, and it is clear that such compounds are included in the scope of the present invention.

The triazolopyrimidine derivative of the formula (I) or its salt can be produced in accordance with the following production processes [1] to [8] and a usual method for producing a salt. Further, the triazolopyrimidine derivative of the formula (I) or its salt can be produced in accordance with the after-mentioned synthetic examples. Now, the respective production processes will be described in detail with reference to the reaction flow charts. PRODUCTION PROCESS [1]

In the production process [1], R^1a is alkyl which may be substituted by A¹, cycloalkyl which may be substituted by A¹, alkenyl which may be substituted by A¹, alkynyl which may be substituted by A¹, or aryl; each of R⁶ and R⁷ which are independent of each other is alkyl; A¹ is OR^2a, alkyl or cycloalkyl; R^2a is hydrogen, alkyl or haloalkyl; and Het is as mentioned above.

The production process [1] is a method for producing a triazolopyrimidine derivative of the formula (1-1) from a compound of the formula (II) and comprises the above steps 1 and 2.

In the step 1 of the production process [1], a compound of the formula (M) and a compound of the formula (III) are condensed to form an α,β-unsatu rated ketone derivative of the formula (IV).

The compound of the formula (III) can be used in a proportion of from 1 to 5 equivalent amounts, preferably from 1 to 3 equivalent amounts per 1 mol of the compound of the formula (II). As a case requires, this reaction can be cried out in the presence of a solvent. So long as the reaction is not impaired, the solvent is not particularly restricted. For example, an alcohol such as methanol, ethanol, propanol or butanol; an aromatic hydrocarbon such as benzene, toluene or xylene; an aliphatic hydrocarbon such as pentane, hexane, heptane, petroleum ether, ligroin or petroleum benzine; an ether such as diethyl ether, dipropyl ether, dibutyl ether, tetrahydrofuran or dioxane; an ester such as methyl acetate or ethyl acetate; a nitrile such as acetonitrile or propiononitrile; an acid amide such as N,N-dimethylformamide, N, N- dimethylacetamide or N-methylpyrrolidinone; a sulfoxide such as dimethylsulfoxide; a sulfone such as sulfolane; a phosphoric acid amide such as hexamethylphosphoramide; a halogenated hydrocarbon such as chloroform, dichloromethane, carbon tetrachloride or 1 ,2-dichloroethane; or a mixed solvent thereof may be mentioned. 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 production process [1], the step 2 of the production process [1] can be continuously carried out without isolating the compound of the formula (IV). In the step 2 of the production process [1], a compound of the formula (IV) and a compound of the formula (V) are condensed to form a compound of the formula (1-1).

The compound of the formula (V) can be used in a proportion of from 1 to 10 equivalent amounts, preferably from 1 to 2.5 equivalent amounts per 1 mol of the compound of the formula (IV). This reaction can usually be carried out in the presence of a solvent. So long as the reaction is not impaired, solvent is not particularly restricted. For example, a carboxylic acid such as acetic acid or propionic acid; an alcohol such as methanol, ethanol, propanol or butanol; an aromatic hydrocarbon such as benzene, toluene or xylene; an aliphatic hydrocarbon such as pentane, hexane, heptane, petroleum ether, ligroin or petroleum benzine; an ether such as diethyl ether, dipropyl ether, dibutyl ether, tetrahydrofuran or dioxane; an ester such as methyl acetate or ethyl acetate; a nitrile such as acetonitrile or propiononitrile; an acid amide such as N,N-dimethylformamide, N,N-dimethylacetamide or N- methylpyrrolidinone; a sulfoxide such as dimethylsulfoxide; a sulfone such as sulfolane; a phosphoric acid amide such as hexamethylphosphoramide; a halogenated hydrocarbon such as chloroform, dichloromethane, carbon tetrachloride or 1 ,2- dichloroethane; or a mixed solvent thereof may be mentioned. Among them, the carboxylic acid is particularly preferred. The reaction temperature is usually from 50 to 150°C, preferably from 80 to 120⁰C. The reaction time is usually from 30 minutes to 100 hours. PRODUCTION PROCESS [2]

In the production process [2], R^3a is alkyl; Z is halogen; and Het is as mentioned above. As the halogen of Z, an atom of fluorine, chlorine, bromine or iodine may be mentioned. The production process [2] is a method for producing a triazolopyrimidine derivative of the formula (1-2) from a compound of the formula (II) and comprises the above steps 1 and 2.

In the step 1 of the production process [2], a compound of the formula (II), carbon disulfide and a compound of the formula (Vl) are reacted to form an α,β- unsaturated ketone derivative of the formula (VII). Carbon disulfide and the compound of the formula (Vl) can be used in a proportion of from 1 to 5 equivalent amounts, preferably from 1 to 3 equivalent amounts per 1 mol of the compound of the formula (II) respectively. 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 such as sodium methoxide, sodium ethoxide or potassium tertiary butoxide. Such a base can be used in a proportion of from 1 to 10 equivalent amounts, preferably from 1 to 3 equivalent amounts per 1 mol of the compound of the formula (II). So long as the reaction is not impaired, the solvent is not particularly restricted. For example, the same solvents mentioned in the step 1 of the production process [1] may be mentioned. The reaction temperature is usually from 0 to 100⁰C, preferably from 10 to 50⁰C. The reaction time is usually from 6 to 48 hours.

In the step 2 of the production process [2], a compound of the formula (VII) and a compound of (V) are condensed to form a compound of the formula (I-2).

The compound of the formula (V) can be used in a proportion of from 1 to 5 equivalent amounts, preferably from 1 to 3 equivalent amounts per 1 mol 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; an alkali metal such as sodium or potassium; an alkali metal alkoxide such as sodium methoxide, sodium ethoxide or potassium tertiary butoxide; an alkali metal carbonate such as sodium carbonate or potassium carbonate; an alkali metal bicarbonate such as sodium bicarbonate or potassium bicarbonate; or an organic base such as triethyl amine or pyridine. Such a base can be used in a proportion of from 1 to 5 equivalent amounts, preferably from 1 to 3 equivalent amounts per 1 mol of the compound of the formula (VII). So long as the reaction is not impaired, the solvent is not particularly restricted. For example, the same solvents mentioned in the step 1 of the production process [1] may be mentioned. Among them, the acid amide is preferred. The reaction temperature is usually from 100 to 200⁰C. The reaction time is usually from 5 minutes to 10 hours. PRODUCTION PROCESS [3]

In the production process [3], the formula (1-2), Het and R^3a are as mentioned above; and na is an integer of 1 or 2.

In the production process [3], a compound of the formula (I-2) and an oxidizing agent are reacted to form a triazolopyrimidine derivative of the formula (I-3).

The oxidizing agent may, for example, be hydrogen peroxide, peracetic acid or m-chloroperbenzoic acid. This reaction can usually be carried out in the presence of a solvent. So long as the reaction is not impaired, the solvent is not particularly restricted. For example, a halogenated hydrocarbon such as chloroform, dichloromethane, carbon tetrachloride or 1 ,2-dichloroethane; a ketone such as acetone or methyl ethyl ketone; an ether such as diethyl ether, dipropyl ether, dibutyl ether, tetrahydrofuran or dioxane; a carboxylic acid such as acetic acid or propionic acid; or a mixed solvent thereof may be mentioned. The oxidizing agent may be used in a proportion of from 1 to 3 equivalent amounts per 1 mol of the compound of the formula (I-2). The reaction temperature is usually from 15°C to a reflux temperature. The reaction time is usually from 1 to 24 hours. PRODUCTION PROCESS [4]

In the production process [4], R^1b is alkyl which may be substituted by A¹, cycloalkyl which may be substituted by A¹, alkenyl which may be substituted by A¹, alkynyl which may be substituted by A¹, halogen, cyano, aryl, or NR³R⁴; and the formula (I-3), Het, A¹, R³ and R⁴ are as mentioned above.

In the production process [4], a compound of the formula (I-3) and a nucleophilic reagent are reacted to form a triazolopyrimidine derivative of the formula (I-4). The nucleophilic reagent may, for example, be a primary or secondary amine such as methylamine, dimethylamine or piperidine; an organic metal reagent such as methyl magnesium bromide, ethyl magnesium bromide, vinyl magnesium bromide, 1- butenyl zinc bromide, 1-propynyl zinc chloride or phenyl magnesium bromide; a halogenating agent such as potassium fluoride, cesium fluoride, tetrabutylammonium fluoride, lithium chloride or sodium bromide; or a metal cyanide such as sodium cyanide, potassium cyanide or copper cyanide.

The nucleophilic reagent can be used in a proportion of from 1 to 5 equivalent amounts, preferably from 1 to 3 equivalent amounts per 1 mol of the compound of the formula (I-3). The reaction can usually be carried out in the presence of a solvent. So long as the reaction is not impaired, the solvent is not particularly restricted. For example, an alcohol such as methanol, ethanol, propanol or butanol; an aromatic hydrocarbon such as benzene, toluene or xylene; an aliphatic hydrocarbon such as pentane, hexane, heptane, petroleum ether, ligroin or petroleum benzine; an ether such as diethyl ether, dipropyl ether, dibutyl ether, tetrahydrofuran or dioxane; an ester such as methyl acetate or ethyl acetate; a nitrile such as acetonitrile or propiononitrile; an acid amide such as N,N-dimethylformamide, N,N-dimethylacetamide or N- methylpyrrolidinone; a sulfoxide such as dimethylsulfoxide; or a mixed solvent thereof may be mentioned. The reaction temperature is usually from -100 to 50⁰C, preferably from -70 to 30°C. The reaction time is usually from 1 minute to 48 hours. PRODUCTION PROCESS [5]

In the production process [5], R¹° is alkyl which may be substituted by A¹, cycloalkyl which may be substituted by A¹, alkenyl which may be substituted by A¹, alkynyl which may be substituted by A¹, or aryl; R⁸ is alkyl; and Het and A¹ are as mentioned above.

The production process [5] is a method for producing a triazolopyrimidine derivative of the formula (I-5) from the compound of a formula (II) and comprises the above steps 1 and 2. In the step 1 of the production process [5], a compound of the formula (II) and a compound of the formula (VIII) are reacted to form a compound of the formula (IX).

The compound of the formula (VIII) can be used in a proportion of from 1 equivalent amount to an excess amount, preferably from 1 to 10 equivalent amounts per 1 mol of the compound of the formula (II). The reaction may be usually carried out in the presence of a base and a solvent. The same bases mentioned in the step 1 of the production process [2] may be mentioned. The base may be used in a proportion of from 1 to 5 equivalent amounts, preferably from 1 to 2 equivalent amounts per 1 mol of the compound of the formula (II). So long as the reaction is not impaired, the solvent is not particularly restricted. For example, an alcohol such as methanol, ethanol, propanol or butanol; an aromatic hydrocarbon such as benzene, toluene or xylene; an aliphatic hydrocarbon such as pentane, hexane, heptane, petroleum ether, ligroin or petroleum benzine; an ether such as diethyl ether, dipropyl ether, dibutyl ether, tetrahydrofuran or dioxane; an acid amide such as N, N- dimethylformamide, N,N-dimethylacetamide or N-methylpyrrolidinone; a sulfoxide such as dimethylsulfoxide; a sulfone such as sulfolane; a halogenated hydrocarbon such as chloroform, dichloromethane, carbon tetrachloride or 1 ,2-dichloroethane; or a mixed solvent thereof may be mentioned. Among them, the ether is preferred. The reaction temperature is usually from 0 to 100°C, preferably from 10 to 80°C. The reaction time is usually from 5 minutes to 24 hours. After the termination of the step 1 of the production process [5], the step 2 of the production process [5] can continuously be carried out without isolating the compound of the formula (IX).

In the step 2 of the production process [5], a compound of the formula (IX) and a compound of the formula (V) are condensed to form a compound of the formula (I-5). The compound of the formula (V) can be used in a proportion of from 1 to 10 equivalent amounts, preferably from 1 to 5 equivalent amounts by 1 mol of the compound of the formula (IX). The reaction can usually be carried out in the presence of a solvent. So long as the reaction is not impaired, the solvent is not particularly restricted. For example, the same solvents in the step 2 of the production process [1] may be mentioned, and among them, the carboxylic acid is preferred. The reaction temperature is usually from 50 to 200°C, preferably from 80 to 150⁰C. The reaction time is usually from 30 minutes to 100 hours. PRODUCTION PROCESS [6]

(X) (K) ( I -5)

In the production process [6], R⁹ is an alkyl; and Het and R^1c are as mentioned above. The production process [6] is a method for producing a triazolopyrimidine derivative of the formula (I-5) from the compound of a formula (X) and comprises the above steps 1 and 2.

In the step 1 of the production process [6], a compound of the formula (X) and a compound of the formula (Xl) are reacted to form a compound of the formula (IX). The compound of the formula (Xl) can be used in a proportion of from 1 equivalent amount to an excess amount, preferably from 1 to 10 equivalent amounts per 1 mol of the compound of the formula (X). The reaction can usually be carried out in the presence of a base and a solvent. As the base, the same bases mentioned in the step 1 of the production process [2] may, for example, be mentioned. The base can be used in a proportion of usually from 1 to 5 equivalent amounts, preferably from 1 to 2 equivalent amounts per 1 mol of the compound of the formula (X). So long as the reaction is not impaired, the solvent is not particularly restricted. For example, the same solvents mentioned in the step 1 of the production process [5] may be mentioned, and among them, the ether is preferred. The reaction temperature is usually from 0 to 100⁰C, preferably from 10 to 80°C. The reaction time is usually from 5 minutes to 24 hours.

In the step 2 of the production process [6], a compound of the formula (IX) and a compound of the formula (V) are condensed to form a compound of the formula (I-5). The reaction may be carried out in the same manner as in the step 2 of the production process [5].

PRODUCTION PROCESS [7]

In the production process [7], R¹⁰ and R¹¹ which are independent of each other, is hydrogen, alkyl or a cycloalkyl; Q is halogen; and Het is as mentioned above. In the production process [7], a compound of the formula (I-6) and a halogenating agent are reacted to form a triazolopyrimidine derivative of the formula (I-

7)-

The halogenating agent may, for example, be N-chlorosuccinimide, N- bromosuccinimide or N-iodosuccinimide. The halogenating agent can be used in a proportion of from 1 to 5 equivalent amounts, preferably from 1 to 2 equivalent amounts per 1 mol of the compound of the formula (I-6). The reaction can usually be carried out in the presence of a radical initiator. The radical initiator may, for example, be benzoyl peroxide or 2,2'-azobis(isobutyronitrile). As a case requires, the reaction may be carried out under light irradiation.

The reaction can usually be carried out in the presence of a solvent. So long as the reaction is not impaired, the solvent is not particularly restricted. For example, a halogenated hydrocarbon such as chloroform, dichloromethane, carbon tetrachloride or 1 ,2-dichloroethane may be mentioned. The reaction temperature is usually from 0 to 100°C, preferably from 10 to 80°C. The reaction time is usually from 5 minutes to 24 hours. PRODUCTION PROCESS [8]

In the production process [8], R^1d is alkyl which may be substituted by A, cycloalkyl which may be substituted by A, alkenyl which may be substituted by A, alkynyl which may be substituted by A, or aryl; Q¹ is halogen; R¹³ is OH, alkyl, cycloalkyl, alkoxy or fluorine; in a case where R¹³ is OH, alkyl, cycloalkyl or alkoxy, p is 2, and in a case where R¹³ is fluorine, p is 3; alkyl or alkoxy for R¹³ may bond each other to form a ring together with the adjacent boron atom; and Het and A are as mentioned above.

In the production process [8], a compound of the formula (XIV) and a boron compound of the formula (XV) are Suzuki coupling-reacted in the presence of a transition metal catalyst to form a triazolopyrimidine derivative of the formula (I-8).

The Suzuki coupling reaction has been studied and published in many publications, and in the steps of the present invention, the Suzuki coupling reaction may be carried out in accordance with a known method (for example, a method described in Synth. Commun., 1981, 11 (7), 513-519 or Synlett., 1992, 207-210). Since in the substituted boron part represented by B(R¹³)_P in the formula (XV), a -BF3 group wherein R¹³ is fluorine, and p is 3 has a negative charge, and the BF₃ group usually form a trifluoroborate salt with an alkali metal such as potassium. The substituted boron represented by B(R¹³)_P in the formula (XV) may, for example, be hydroxyboron, alkylboron, alkoxyboron or trifluoroborate. The boron compound in the formula (XV) can be used in a proportion of from 0.5 to 1 equivalent amount, preferably from 0.5 to 0.8 equivalent amount per 1 mol of the compound of the formula (XIV).

The transition metal catalyst used in the reaction is a transition metal compound or a complex of a transition metal compound with an optional ligand. For example, paradium-carbon (Pd/C), tetrakis(triphenylphosphine)palladium(0), bis(dibenzylidene acetone)palladium(O), tetrakis(dibenzylidene acetone)dipalladium(O), palladium acetate(ll)-triphenylphosphine or palladium acetate(ll)- tricyclohexylphosphine may be mentioned. In the case of the complex, (1) a preliminarily isolated complex may be used, or (2) a complex wherein a transition metal compound and a ligand are mixed in an optional reaction solvent may be used without isolation. The transition metal catalyst can be used in a proportion of from 0.001 to 0.2 equivalent amount, preferably from 0.01 to 0.1 equivalent amount per 1 mol of the compound of the formula (XIV). 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 cesium carbonate; a hydrogen carbonate of an alkali metal such as sodium hydrogen carbonate; an alkaline earth metal carbonate such as calcium carbonate; an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide; an alkaline earth metal hydroxide such as calcium hydroxide; an alkali metal fluoride such as cesium fluoride or potassium fluoride; or an organic base such as triethylamine, pyridine or 4-(N,N-dimethylamino)pyridine. The base can be used in a proportion of usually from 1 to 20 equivalent amounts, preferably from 1 to 3 equivalent amounts per 1 mol of the compound of the formula (XIV).

The reaction can usually be carried out in the presence of a solvent. So long as the reaction is not impaired, the solvent is not particularly restricted. For example, water; an alcohol such as methanol, ethanol, propanol or butanol; an aromatic hydrocarbon such as benzene, toluene or xylene; an aliphatic hydrocarbon such as pentane, hexane, heptane, petroleum ether, ligroin or petroleum benzine; an ether such as diethyl ether, dipropyl ether, dibutyl ether, tetrahydrofuran, dioxane, ethylene glycol dimethyl ether; a nitrile such as acetonitrile or propiononitrile; a halogenated hydrocarbon such as chloroform, dichloromethane, carbon tetrachloride or 1 ,2- dichloroethane; or a mixed solvent thereof may be mentioned. The reaction temperature is usually from 15°C to a reflux temperature of a reaction mixture, preferably from 40°C to a reflux temperature of a reaction mixture. The reaction time varies depending on the reaction temperature, the amount of reactant, reaction pressure, etc., however, it is usually from 1 to 96 hours.

The boron compound in the formula (XV) is available in markets or can be synthesized by a known method. For example, the 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 tert-butyl lithium.

In the above respective production processes, the production process [1] or the production process [6] is particularly preferred. For example, the compound of the formula (XIV) in the production process [8] can be produced by the following production process [A]. PRODUCTION PROCESS [A]

(X E ) (XI) (XN)

In the production process [A], R¹² is alkyl; and R^1d and Q¹ are as mentioned above. As the halogen for Q¹, each atom of chlorine, bromine or iodine may be mentioned.

The production process [A] is a method for producing a compound of the formula (XIV) from a compound of the formula (XII) and comprises the above steps 1 and 2. In the step 1 of the production process [A], a compound of the formula (XII) and a compound of the formula (V) are condensed to form a compound of the formula (XIII).

The compound of the formula (V) can be used in a proportion of usually from 1 to 10 equivalent amounts, preferably from 1 to 3 equivalent amounts per 1 mol of the compound of the formula (XII). The reaction can usually be carried out in the presence of a solvent. So long as the reaction is not impaired, the solvent is not particularly restricted. For example, 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 propiononitrile; an acid amide such as N.N-dimethylformamide, N,N-dimethylacetamide or N- methylpyrroiidinone; a sulfoxide such as dimethylsulf oxide; a sulfone such as sulfolane; a phosphoric acid amide such as hexamethylphosphoramide; or a mixed solvent thereof may be mentioned. 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 the production process [A] is a step of halogenating the compound of the formula (XIII) and comprises:

(a) a step of reacting a compound of the formula (XIII) with a chlorinating agent or brominating agent to form a compound of the formula (XIV) (wherein Q¹ is chlorine or bromine) and (b) as a case requires, a step of reacting the compound of the formula (XIV) formed in (a) (wherein Q¹ is chlorine or bromine) with ammonia, followed by reaction with an iodinating agent in the presence of a diazonating agent to form a compound of the formula (XIV) (wherein Q¹ is iodine). Now, each step of (a) and (b) will be described in detail. (a) The chlorinating agent may, for example, be phosphorus oxychloride, phosphorus trichloride or phosphorus pentachloride. The brominating agent may, for example, be phosphorus oxybromide, phosphorus tribromide or phosphorus pentabromide. The chlorinating agent or the brominating agent can be used in a proportion of usually from 2 to 30 equivalent amounts per 1 mol of the compound of the formula (XIII). As a case requires, the reaction can be carried out in the presence of a solvent. So long as the reaction is not impaired, the solvent is not particularly restricted. For example, a halogenated hydrocarbon such as dichloromethane may be mentioned. The reaction temperature is usually from 0°C to a reflux temperature of a reaction mixture, preferably from 20⁰C to a reflux temperature of a reaction mixture. The reaction time is usually from 1 to 48 hours.

The step (b) comprises a former reaction wherein the compound of the formula (XIV) formed in step (a) (wherein Q¹ is chlorine or bromine) and ammonia are reacted and a later reaction wherein a resulting compound is reacted with a iodinating agent in the presence of a diazonating agent. The former reaction in (b) can usually be carried out in the presence of a base.

It is particularly preferred to employ an excess amount of ammonia which may also be used as a base. The former reaction in (b) can usually be carried out in the presence of a solvent. So long as the reaction is not impaired, the solvent is not particularly restricted. For example, an aromatic hydrocarbon such as benzene, toluene or xylene; an aliphatic hydrocarbon such as pentane, hexane, heptane, petroleum ether, ligroin or petroleum benzine; a halogenated hydrocarbon such as chloroform, dichloromethane, carbon tetrachloride or 1 ,2-dichloroethane; or a mixed solvent thereof may be mentioned. The reaction temperature is from 20°C to a reflux temperature of a reaction mixture, preferably from 40°C to a reflux temperature of a reaction mixture. The reaction time is usually from 2 to 48 hours.

In the later reaction of (b), the diazolating agent may, for example, be an optional alkyl ester of nitrous acid, and among them, isopentyl nitrite is preferred. The diazonating agent can be used in a proportion of from 1 to 5 equivalent amounts per 1 mol of the compound of the formula (XIV) (wherein Q¹ is a chlorine or bromine atom). The iodinating agent may, for example, be iodine or diiodomethane. The iodinating agent may be used in a proportion of from 1 to 5 equivalent amounts per 1 mol of the compound of the formula (XIV) (wherein Q¹ is chlorine or bromine). The later reaction of (b) can usually be carried out in the presence of a solvent.

So long as the reaction is not impaired, the solvent is not particularly restricted. For example, an aliphatic hydrocarbon such as pentane, hexane, heptanes, petroleum ether, ligroin or petroleum benzine; an ether such as diethyl ether, dipropyl ether, dibutyl ether, tetrahydrofuran or dioxane; an ester such as methyl acetate or ethyl acetate; a nitrile such as acetonitrile or propiononitrile; or a mixed solvent thereof may be mentioned. In a case where the alkyl ester of nitrous acid is used as the diazonating agent, diiodomethane which is an iodinating agent can be used as a cosolvent. The reaction temperature is usually from 60 to 120°C, preferably from 70 to 110°C. The reaction time is from 1 to 48 hours. Preferred embodiments of pesticides containing the compounds of the present invention will be described below. The pesticides containing the compounds of the present invention are particularly useful, for example, as agents for controlling various pests which become problematic in the agricultural and horticultural fields, i.e. agricultural and horticultural pesticides, or as agents for controlling pests which are parasitic on animals i.e. pesticides against parasites on animals.

The agricultural and horticultural pesticides containing the compounds of the present invention are useful as an insecticide, a miticide, a nematicide or a soil pesticide, and they are effective for controlling plant parasitic mites such as two- spotted spider mite (Tetranvchus urticae), carmine spider mite (Tetranvchus cinnabarinus), kanzawa spider mite (Tetranvchus kanzawai), citrus red mite (Panonvchus citrfl, European red mite (Panonvchus ulmfl. broad mite (Polvphaqotarsonemus latus), pink citrus rust mite (Aculops pelekassQ and bulb mite (Rhizoglvphus echinopus); aphids such as green peach aphid (Mvzus persicae) and cotton aphid (Aphis qossypii); agricultural insect pests such as diamondback moth (Plutella xylostella), cabbage armyworm (Mamestra brassjcae), common cutworm (Spodoptera litura), codling moth (cvdia pomonella), bollworm (Heliothis zea), tobacco budworm (Heliothis virescens), gypsy moth (Lvmantria dispar), rice leafroller (Cnaphalocrocis medinalis), smaller tea tortrix (Adoxophyes sp_.), Colorado potato beetle (Leptinotarsa decemlineata). cucurbit leaf beetle (Aulacophora femoralis). boll weevil (Anthonomus qrandis), planthoppers, leafhoppers, scales, bugs, whiteflies, thrips, grasshoppers, anthomyiid flies, scarabs, black cutworm (Agrotis ipsilon). cutworm (Aqrotis seqetunrO and ants; plant parasitic nematodes such as root-knot nematodes, cyst nematodes, root-lesion nematodes, white-tip nematode (Aphelenchoides bessevi), strawberry bud nematode (Nothotylenchus acris), and pine wood nematode (Bursaphelenchus xylophilus); gastropods such as slugs and snails; soil pests such as isopods such as pillbugs (Armadillidium vulqarei and pillbugs (Porcellio scaber); hygienic insect pests such as tropical rat mite (Ornithonvssus bacoti), cockroaches, housefly (Musca domestica) and house mosquito (Culex pipiens): stored grain insect such as angoumois grain moth (Sitotroqa cerealella), adzuki bean weevil (Callosobruchus chinensis), red flour beetle (Tribolium castaneum) and mealworms; household goods insect pests such as casemaking clothes moth (Tinea pellionella), black carpet beetle (Attagenus iaponicus) and subterranean termites; domestic mites such as mold mite (Tyrophagus putrescentiae),

Dermatophagoides farinae, Chelacaropsis moorei, and so on. Among them, the agricultural and horticultural pesticides containing the compounds of the present invention are particularly effective for controlling plant parasitic mites, agricultural insect pests, plant parasitic nematodes or the like. Particularly, they are more effective for controlling plant parasitic mites and agricultural insect pests, and accordingly they are useful as an insecticide or miticide. Further, they are effective against insect pests having acquired resistance to organophosphorus, carbamate, synthetic pyrethroid and/or neonicotinoid insecticides. Moreover, the compounds of the present invention have excellent systemic properties, and by the application of the agricultural and horticultural pesticides containing the compounds of the present invention to soil treatment, not only noxious insects, noxious mites, noxious nematodes, noxious gastropods and noxious isopods in soil but also foliage pests can be controlled.

Another preferred embodiments of the pesticides containing compounds of the present invention may be agricultural and horticultural pesticides which collectively control the above-mentioned plant parasitic mites, agricultural insect pests, plant parasitic nematodes, gastropods and soil pests.

The agricultural and horticultural pesticide containing the compound of the present invention, is usually formulated by mixing the compound with various agricultural additives and used in the form of a formulation such as a dust, granules, dust granules, water-dispersible granules, a wettable powder, a water-based suspension concentrate, an oil-based suspension concentrate, a water soluble powder, water soluble granules, an emulsifiable concentrate, a soluble concentrate, a paste, an aerosol, an oil solution, a smoking pesticide, microcapsules or an ultra low-volume formulation. However, so long as it is suitable for the purpose of the present invention, it may be formulated into any type of formulation which is commonly used in this field. Such additives include solid carriers such as diatomaceous earth, calcium carbonate, talc, kaoline, bentonite, sericite, clay, zeolite, pumice stone, quartz sand, pearlite, white carbon, sodium carbonate, sodium sulfate, ammonium sulfate, urea, starch and succharide; solvents such as water, xylene, C₁₀ alkylbenzene, alkyl naphthalene, isophorone, methyl isobutyl ketone, cyclohexanone, γ-butyrolactone, cyclohexane, dimethylsulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2- pyrrolidone, and alcohol; anionic surfactants such as a salt of fatty acid, a benzoate, an alkylsulfosuccinate, a dialkylsulfosuccinate, a polycarboxylate, a salt of alkylsulfuric acid ester, an alkyl sulfate, an alkylaryl sulfate, an alkyl diglycol ether sulfate, a salt of alcohol sulfuric acid ester, an alkyl sulfonate, an alkylaryl sulfonate, an aryl sulfonate, a lignin sulfonate, an alkyldiphenyl ether disulfonate, a polystyrene sulfonate, a salt of alkylphosphoric acid ester, an alkylaryl phosphate, a styrylaryl phosphate, a salt of polyoxyethylene alkyl ether sulfuric acid ester, a polyoxyethylene alkylaryl ether sulfate, a salt of polyoxyethylene alkylaryl ether sulfuric acid ester, a polyoxyethylene alkyl ether phosphate, a salt of polyoxyethylene alkylaryl phosphoric acid ester, and a condensate of naphthalene sulfonate with formaldehyde; nonionic surfactants such as a sorbitan fatty acid ester, a glycerin fatty acid ester, a fatty acid polyglyceride, a fatty acid alcohol polyglycol ether, acetylene glycol, acetylene alcohol, an oxyalkylene block polymer, a polyoxyethylene alkyl ether, a polyoxyethylene alkylaryl ether, a polyoxyethylene styrylaryl ether, a polyoxyethylene glycol alkyl ether, a polyethylene glycol, a polyoxyethylene fatty acid ester, a polyoxyethylene sorbitan fatty acid ester, a polyoxyethylene glycerin fatty acid ester, a polyoxyethylene hydrogenated castor oil, and a polyoxypropylene fatty acid ester; vegetable and mineral oils such as olive oil, kapok oil, castor oil, palm oil, camellia oil, coconut oil, sesame oil, com oil, rice bran oil, peanut oil, cottonseed oil, soybean oil, rapeseed oil, linseed oil, tung oil, and liquid paraffins; and so on. Each of the components as such additives may be one or more suitably selected for use, so long as the purpose of the present invention can thereby be accomplished. Further, other than the above-mentioned additives, some among those known in this field may suitably be selected for use. For example, various additives or adjuvants which are commonly used, such as a thickener, an anti-settling agent, an anti-freezing agent, a dispersion stabilizer, a phytotoxicity reducing agent, an anti-mold agent, an anti-foaming agent, an anti-bonding agent, a lubricant auxiliary, a desiccant, an antioxidant, ultraviolet absorbing agent, and so on, may also be employed.

The weight ratio of the compound of the present invention to the various additives including adjuvants is usually from 0.001 :99.999 to 95:5, preferably from 0.005:99.995 to 90:10. In the actual application of such a formulation, it may be used as it is, or may be diluted to a predetermined concentration with a diluent such as water, and various spreaders e.g. surfactants, vegetable oils or mineral oils may be added thereto, as the case requires.

The application of the agricultural and horticultural pesticide containing the compound of the present invention cannot generally be defined, as it varies depending upon the weather conditions, the type of the formulation, the application season, the application site or the types or degree of outbreak of the pest insects. However, it is usually applied in a concentration of the active ingredient being from 0.05 to 800,000 ppm, preferably from 0.5 to 500,000 ppm, and the dose 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, per hectare. Further, agricultural and horticultural pesticides as another preferred embodiment of pesticides containing the compounds of the present invention may be applied in accordance with the above-described application of pesticides. The present invention includes such a method for controlling pests, particularly for controlling plant parasitic mites, agricultural insect pests or plant parasitic nematodes by such applications.

Various formulations of agricultural and horticultural pesticides containing the compounds of the present invention or their diluted compositions may be applied by conventional methods for application which are commonly employed, such as spraying (e.g. spraying, jetting, misting, atomizing, powder or grain scattering or dispersing in water), soil application (e.g. mixing or drenching), surface application (e.g. coating, powdering or covering) or impregnation to obtain poisonous feed. Further, it is possible to feed domestic animals with a food containing the above active ingredient and to control the outbreak or growth of pests, particularly insect pests, with their excrements. Furthermore, the active ingredient may also be applied by a so-called ultra low-volume application method. In this method, the composition may be composed of 100% of the active ingredient.

Further, the agricultural and horticultural pesticides containing compounds of the present invention may be mixed with or may be used in combination with other agricultural chemicals, fertilizers or phytotoxicity-reducing agents, whereby synergistic effects or activities may sometimes be obtained. Such other agricultural chemicals include, for example, a herbicide, an insecticide, a miticide, a nematicide, a soil pesticide, a fungicide, an antivirus agent, an attractant, an antibiotic, a plant hormone, a plant growth regulating agent, and so on. Especially, with a mixed pesticide having a compound of the present invention mixed with or used in combination with one or more active compounds of other agricultural chemicals, the application range, the application time, the pesticidal activities, etc. may be improved to preferred directions. The compound of the present invention and the active compounds of other agricultural chemicals may separately be formulated so that they may be mixed for use at the time of application, or they may be formulated together. The present invention includes such a mixed pesticidal composition.

The mixing weight ratio of the compound of the present invention to the active compounds of other agricultural chemicals can not generally be defined, since it varies depending upon the weather conditions, the types of formulations, the application time, the application site, the types or degree of outbreak of insect pests, etc., but it is usually within a range of from 1 :300 to 300:1 , preferably from 1 :100 to 100:1 , by weight. Further, the dose for the application is such that the total amount of the active compounds is from 0.1 to 50,000 g, preferably from 1 to 30,000 g, per hectare. The present invention includes a method for controlling pests by an application of such a mixed pesticide composition.

The active compounds of insect pest control agents such as insecticides, miticides, nematicides or soil pesticides in the above-mentioned other agricultural chemicals, include, for example, (by common names, some of them are still in an application stage, or test codes) organic phosphate compounds such as profenofos, dichlorvos, fenamiphos, fenitrothion, EPN, diazinon, chlorpyrifos, chlorpyrifos-methyl, acephate, prothiofos, fosthiazate, cadusafos, dislufoton, isoxathion, isofenphos, ethion, etrimfos, quinalphos, dimethylvinphos, dimethoate, sulprofos, thiometon, vamidothion, pyraclofos, pyridaphenthion, pirimiphos-methyl, propaphos, phosalone, formothion, malathion, tetrachlorvinphos, chlorfenvinphos, cyanophos, trichlorfon, methidathion, phenthoate, ESP, azinphos-methyl, fenthion, heptenophos, methoxychlor, parathion, phosphocarb, demeton-S-methyl, monocrotophos, methamidophos, imicyafos, parathion-methyl, terbufos, phosphamidon, phosmet and phorate; carbamate compounds such as carbaryl, propoxur, aldicarb, carbofuran, thiodicarb, methomyl, oxamyl, ethiofencarb, pirimicarb, fenobucarb, carbosulfan, benfuracarb, bendiocarb, furathiocarb, isoprocarb, metolcarb, xylylcarb, XMC and fenothiocarb; nereistoxin derivatives such as cartap, thiocyclam, bensultap and thiosultap-sodium; organic chlorine compounds such as dicofol, tetradifon, endosulfan, dienochlor and dieldrin; organic metal compounds such as fenbutatin oxide and cyhexatin; pyrethroid compounds such as fenvalerate, permethrin, cypermethrin, deltamethrin, cyhalothrin, tefluthrin, ethofenprox, flufenprox, cyfluthrin, fenpropathrin, flucythrinate, fluvalinate, cycloprothrin, lambda-cyhalothrin, pyrethrins, esfenvalerate, tetramethrin, resmethrin, protrifenbute, bifenthrin, zeta-cypermethrin, acrinathrin, alpha-cypermethrin, allethrin, gamma-cyhalothrin, theta-cypermethrin, tau-fluvalinate, tralomethrin, profluthrin, beta- cypermethrin, beta-cyfluthrin, metofluthrin, phenothrin and flumethrin; benzoylurea compounds such as diflubenzuron, chlorfluazuron, teflubenzuron, flufenoxuron, triflumuron, hexaflumuron, lufenuron, novaluron, noviflumuron, bistrifluron and fluazuron; juvenile hormone-like compounds such as methoprene, pyriproxyfen, fenoxycarb and diofenolan; pyrazole compounds such as fenpyroximate, fipronil, tebufenpyrad, ethiprole, tolfenpyrad, acetoprole, pyrafluprole and pyriprole; neonicotinoids such as imidacloprid, nitenpyram, acetamiprid, thiacloprid, thiamethoxam, clothianidin, dinotefuran and nithiazine; hydrazine compounds such as tebufenozide, methoxyfenozide, chromafenozide and halofenozide; pyridine compounds such as pyridalyl and flonicamid; tetronic acid compounds such as spirodiclofen; strobilurin compounds such as fluacrypyrim; pyrimidinamine compounds such as flufenerim; dinitro compounds; organic sulfur compounds; urea compounds; triazine compounds; hydrazone compounds; and other compounds such as buprofezin, hexythiazox, amitraz, chlordimeform, silafluofen, triazamate, pymetrozine, pyrimidifen, chlorfenapyr, indoxacarb, acequinocyl, etoxazole, cyromazine, 1 ,3-dichloropropene, diafenthiuron, benclothiaz, bifenazate, spiromesifen, spirotetramat, propargite, clofentezine, metaflumizone, flubendiamide, cyflumetofen, chlorantraniliprole, cyenopyrafen, pyrifluquinazon, fenazaquin, pyridaben, amidoflumet, chlorobenzoate, sulfluramid, hydramethylnon, metaldehyde, HGW 86, ryanodine and verbutin. Further, microbial pesticides such as insecticidal crystal protein produced by Bacillus thuringiensis aizawai, Bacillus thuringiensis kurstaki, Bacillus thuringiensis israelensis, Bacillus thuringiensis japonensis, Bacillus thuringiensis tenebrionis or Bacillus thuringiensis, insect viruses, etomopathogenic fungi, and nematophagous fungi; antibiotics or semisynthetic antibiotics such as avermectin, emamectin-benzoate, milbemectin, milbemycin, spinosad, ivermectin, lepimectin, DE-175, abamectin, emamectin and spinetoram; natural products such as azadirachtin and rotenone; and repellents such as deet may, for example, be mentioned. The fungicidal active compounds in the above-mentioned other agricultural chemicals include, for example, (by common names, some of them are still in an application stage, or test codes of Japan Plant Protection Association) anilinopyrimidine compounds such as mepanipyrim, pyrimethanil, cyprodinil and ferimzone; triazolopyrimidine compounds such as 5-chloro-7-(4-methylpiperidin-1-yl)-6- (2,4,6-trifluorophenyl)[1 ,2,4]triazolo[1 ,5-a]pyrimidine; pyridinamine compounds such as fluazinam; azole compounds such as triadimefon, bitertanol, triflumizole, etaconazole, propiconazole, penconazole, flusilazole, myclobutanil, cyproconazole, tebuconazole, hexaconazole, furconazole-cis, prochloraz, metconazole, epoxiconazole, tetraconazole, oxpoconazole fumarate, sipconazole, prothioconazole, triadimenol, flutriafol, difenoconazole, fluquinconazole, fenbuconazole, bromuconazole, diniconazole, tricyclazole, probenazole, simeconazole, pefurazoate, ipconazole and imibenconazole; quinoxaline compounds such as quinomethionate; dithiocarbamate compounds such as maneb, zineb, mancozeb, polycarbamate, metiram, propineb and thiram; organic chlorine compounds such as fthalide, chlorothalonil and quintozene; imidazole compounds such as benomyl, thiophanate-methyl, carbendazim, thiabendazole, fuberiazole and cyazofamid; cyanoacetamide compounds such as cymoxanil; phenylamide compounds such as metalaxyl, metalaxyl-M, mefenoxam, oxadixyl, ofurace, benalaxyl, benalaxyl-M (another name: kiralaxyl, chiralaxyl), furalaxyl and cyprofuram; sulfenic acid compounds such as dichlofluanid; copper compounds such as cupric hydroxide and oxine copper; isoxazole compounds such as hymexazol; organophosphorus compounds such as fosetyl-AI, tolclofos-methyl, edifenphos, iprobenfos, S-benzyl O,0-diisopropylphosphorothioate, O-ethyl S, S- diphenylphosphorodithioate and aluminum ethylhydrogen phosphonate; N- halogenothioalkyl compounds such as captan, captafol and folpet; dicarboximide compounds such as procymidone, iprodione and vinclozolin; benzanilide compounds such as flutolanil, mepronil, zoxamid and tiadinil; anilide compounds such as carboxin, oxycarboxin, thifluzamide, penthiopyrad, boscalid, isothianil, bixafen and mixture of 2 sy/7-isomers 3-(difluoromethyl)-1 -methyl-Λ/-[(1 RS,4SR,9 RS)-1 ,2,3,4-tetrahydro-9- isopropyl-1 ,4-methanonaphthalen-5-yl]pyrazole-4-carboxamide and 2 antf-isomers 3- (difluoromethyl)-1-methyl-/V-[(1 RSASRgSR)-1 ,2,3,4-tetrahydro-9-isopropyl-1 ,4- methanonaphthalen-5-yl]pyrazole-4-carboxamide (isopyrazam); piperazine compounds such as triforine; pyridine compounds such as pyrifenox; carbinol compounds such as fenarimol and flutriafol; piperidine compounds such as fenpropidine; morpholine compounds such as fenpropimorph, spiroxamine and tridemorph; organotin compounds such as fentin hydroxide and fentin acetate; urea compounds such as pencycuron; cinnamic acid compounds such as dimethomorph and flumorph; phenylcarbamate compounds such as diethofencarb; cyanopyrrole compounds such as fludioxonil and fenpiclonil; strobilurin compounds such as azoxystrobin, kresoxim- methyl, metominofen, trifloxystrobin, picoxystrobin, oryzastrobin, dimoxystrobin, pyraclostrobin and fluoxastrobin; oxazolidinone compounds such as famoxadone; thiazolecarboxamide compounds such as ethaboxam; siiylamide compounds such as silthiopham; aminoacid amidecarbamate compounds such as iprovalicarb, benthiavalicarb-isopropyl and methyl N-(isopropoxycarbonyl)-L-valyl-(3RS)-3-(4- chlorophenyl)-β-alaninate (valifenalate); imidazoiidine compounds such as fenamidone; hydroxanilide compounds such as fenhexamid; benzenesulfonamide compounds such as flusulfamide; oxime ether compounds such as cyflufenamid; phenoxyamide compounds such as fenoxanil; antibiotics such as validamycin, kasugamycin and polyoxins; guanidine compounds such as iminoctadine and dodine; quinoline compounds such as 6-tert-butyl-8-fluoro-2,3-dimethylquinolin-4-yl acetate (tebufloquin); thiazolidine compounds such as 2-[2-fluoro-5-(trifluoromethyl)phenylthio]- 2-[3-(2-methoxyphenyl)thiazolidin-2-ylidene]acetonitrile (flutianil); and other compounds such as isoprothiolane, pyroquilon, diclomezine, quinoxyfen, propamocarb hydrochloride, chloropicrin, dazomet, metam-sodium, nicobifen, metrafenone, MTF- 753, UBF-307, diclocymet, proquinazid, amisulbrom, pyribencarb, mandipropamid, fluopicolide, carpropamid, meptylidinocap, fluopyram, BCF-051 , BCM-061 and BCM- 062.

Further, agricultural chemicals which may be used in admixture with or in combination with the compounds of the present invention, may, for example, be the active ingredient compounds in the herbicides as disclosed in The Pesticide Manual (14th edition), particularly those of soil treatment type.

The pesticides against parasites on animals are effective for controlling e.g. external parasites which are parasitic on the body surface of host animals (such as the back, the axilla, the lower abdomen or inside of the thigh) or internal parasites which are parasitic in the body of host animals (such as the stomach, the intestinal tract, the lung, the heart, the liver, the blood vessels, the subcutis or lymphatic tissues), but they are particularly effective for controlling the external parasites.

The external parasites may, for example, be animal parasitic acarus or fleas. Their species are so many that it is difficult to list all of them, and therefore, their typical examples will be given.

The animal parasitic acarus may, for example, be ticks such as Boophilus microplus, Rhipicephalus sanguineus. Haemaphvsalis lonqicornjs, Haemaphvsalis flava. Haemaphvsalis campanulata, Haemaphvsalis concinna. Haemaphvsalis japonica, Haemaphvsalis kitaokai, Haemaphvsalis ias, Ixodes ovatus. Ixodes nipponensis, Ixodes persulcatus, Amblvomma testudinarium. Haemaphvsalis megaspinosa, Dermacentor reticulatus, and Dermacentor taiwanesis: red mite (Dermanvssus gallinae); northern fowl mites such as Ornithonvssus sylviarum, and Qrnithonvssus bursa; trombiculidae such as Eutrombicula wichmanni. Leptotrombidium akamushi, Leptotrombidium pallidum, Leptotrombidium fuji, Leptotrombidium tosa, Neotrombicula autumnalis. Eutrombicula alfredduαesi. and Helenicula miyaqawai; cheyletidae such as Cheyletiella yasguri, Cheyletiella parasitivorax. and Cheyletiella blakei; sarcoptic mange mites such as Psoroptes cuniculi, Chorioptes bovis, Otodectes cynotis, Sarcoptes scabiei, and Notoedres cati: and Demodicidae such as Demodex cam^'s. The pesticides against parasites on animals, containing the compounds of the present invention, are particularly effective for the control of ticks among them. The fleas may, for example, be externally parasitic wingless insects belonging to Siphonaptera, more specifically, fleas belonging to Pulicidae. Ceratephyllus, etc. Fleas belonging to Pulicidae may for example, be Ctenocephalides canis, Ctenocephalides felis. Pulex irritans, Echidnophaαa gallinacea. Xenopsylla cheopis. Leptopsylla segnis, Nosopsyllus fasciatus, and Monopsyllus anisus. The pesticides against parasites on animals, containing the compounds of the present invention, are particularly effective for the control of fleas belonging to Pulicidae, particularly Ctenocephalides canis and Ctenocephalides felis, among them.

Other external parasites may, for example, be sucking lice (Anoplura) such as shortnosed cattle louse (Haematopinus eurysternus), horse sucking louse (Haematopinus asini), sheep louse, longnosed cattle louse (Linognathus vituli), and head louse (Pediculus capitis); biting lice such as dog biting louse (Trichodectes canis); and blood-sucking dipterous insects such as horsefly (Tabanus tπgonus), biting midges (Culicoides schujtzei), and blackfly (Simulium ornatum). Further, the internal parasites may, for example, be nematodes such as lung worms, whipworms (Trichuris). tuberous worms, gastric parasites, ascaris, and filarioidea; cestoda such as Spirometra erinacei, Diphyllobothrium latum, Dipylidium caninum. Taenia multiceps, Echinococcus granulosus, and Echinococcus multilocularis: trematoda such as Schistosoma japonicum and Fasciola hepatica; and protozoa such as coccidia, malaria parasites (Plasmodium malariae), intestinal sarcocyst, toxoplasma, and Cryptosporidium. The host animals may, for example, be pet animals, domestic animals, and poultry, such as dogs, cats, mice, rats, hamsters, guinea pigs, squirrels, rabbits, ferrets, birds (such as pigeons, parrots, hill mynas, Java sparrows, honey parrots, lovebirds and canaries), cows, horses, pigs, sheep, ducks and chickens. The pesticides against parasites on animals, containing the compounds of the present invention, are particularly effective for the control of pests parasitic on pet animals or domestic animals, especially for the control of external parasites, among them. Among pet animals or domestic animals, they are effective particularly for dogs and cats, cows and horses.

When the compound of the present invention is used as a pesticide against parasites on animals, it may be used as it is or may be used together with suitable additives, as formulated into various formulations such as a dust, granules, dust granules, tablets, microcapsules, a soluble concentrate, an emulsifiable concentrate, an oil solution, water soluble powder, water soluble granules, a water-based suspension concentrate, an oil-based suspension concentrate, a wettable powder, water dispersible granules, a paste and a smoking pesticide. In addition to such formulations, it may be formulated into any type of formulation which is commonly used in this field, so long as it is suitable for the purpose of the present invention. The additives to be used for formulations may, for example, be anionic surfactants or nonionic surfactants exemplified above as additives for formulation of agricultural and horticultural pesticides; a cationic surfactant such as cetyl trimethylammonium bromide; a solvent such as water, N,N-dimethylacetamide, N,N-dimethylformamide, N- methyl-2-pyrrolidone, cyclohexanone, isopropanol, ethylene glycol, propylene glycol, polyethylene glycol, liquid polyoxyethylene glycol, butyl diglycol, 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; an antioxidant such as butylhydroxyanisole, butylhydroxytoluene, ascorbic acid, sodium hydrogenmetasulfite, propyl gallate or sodium thiosulfate; a coating film-forming agent such as polyvinylpyrrolidone, polyvinyl alcohol, or a copolymer of vinyl acetate and vinyl pyrrolidone; the vegetable oils and mineral oils as exemplified above as additives for formulation of agricultural and horticultural pesticides; a carrier such as lactose, sucrose, glucose, starch, wheat flour, clay, bentonite, talc, diatomaceous earth, calcium carbonate, white carbon, sodium sulfate, ammonium sulfate, urea; and so on. One or more of the respective components of these additives may be suitably selected for use, so long as such will not depart from the purpose of the present invention. Further, other than the above-mentioned additives, some among those known in this field may suitably be selected for use, and still further, some among the above-mentioned various additives to be used in the agricultural and horticultural field may suitably be selected for use.

The blend ratio of the compound of the present invention 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 as it is, or may be diluted to a predetermined concentration with a diluent such as water, and various spreaders (e.g. surfactants, vegetable oils or mineral oils) may be added thereto, as the case requires.

Administration of the compound of the present invention to a host animal is carried out orally or parenterally. As an oral administration method, a method of administering a tablet, a liquid agent, a capsule, a wafer, a biscuit, a minced meat or other feed, containing the compound of the present invention, may be mentioned. As a parenteral administration method, there may, for example, be mentioned a method wherein the compound of the present invention is formulated into a suitable formulation and then taken into the body by e.g. intravenous administration, intramuscular administration, intradermal administration, hypodermic administration, etc.; a method wherein it is administered on the body surface by spot-on treatment, pour-on treatment or spray treatment; or a method of embedding a resin fragment or the like containing the compound of the present invention under the skin of the host animal.

The dose of the compound of the present invention to a host animal varies depending upon the administration method, the purpose of administration, the deceased symptom, etc., but it is usually administered in a proportion of from 0.01 mg to 100 g, preferably from 0.1 mg to 10 g, per 1 kg of the body weight of the host animal.

The present invention also includes a method for controlling a pest by the above-mentioned administration method or by the above-mentioned dose, particularly a method for controlling external parasites or internal parasites.

Further, in the present invention, by controlling pests parasitic on animals as described above, it is possible to prevent or cure various diseases of the host animal thereby caused in some cases. Thus, the present invention also includes a preventive or therapeutic agent for an animal disease caused by parasites, containing the compound of the present invention as an active ingredient, and a method for preventing or curing an animal disease caused by parasites.

When the compound of the present invention is used as a pesticide against parasites on animals, various vitamins, minerals, amino acids, nutrients, enzymes, antipyretics, sedatives, antiphlogistics, fungicides, colorants, aromatic substances, preservatives, etc., may be used in admixture with or in combination with the additives. Further, as the case requires, other animal drugs or agricultural chemicals, such as vermicides, anti-coccidium agents, insecticides, miticides, pulicides, nematicides, bactericides or antibacterial agents, may be mixed or combined for use, whereby improved effects may sometimes be obtained. The present invention includes such a mixed pesticidal composition having the above-mentioned various components mixed or combined for use, and further a method for controlling a pest by using it, particularly a method for controlling external parasites or internal parasites.

The preferred embodiment of the compound of the formula (I) is a triazolopyrimidine derivative wherein in the formula (I), R¹ is alkyl which may be substituted by A, cycloalkyl which may be substituted by A, halogen, cyano, S(O)_nR³ or NR³R⁴, or its salt. But the present invention is not by no means thereby restricted.

EXAMPLES Now, Examples of the present invention will be described, but it should be understood that the present invention is by no means thereby restricted.

First, synthetic examples of the compound of the present invention will be described.

PREPARATION EXAMPLE 1 Preparation of 5-methyl-7-(4-(trifluoromethyl)pyrimidin-2-yl)-[1 ,2,4]triazolo[1 ,5- a]pyrimidine (compound No.8)

(1) A solution wherein 470 mg of 2-acetyl-4-trifluoromethylpyrimidine and 1 ml of N,N-dimethylacetamide dimethylacetal were dissolved in 10 ml of toluene was stirred for 5 hours under heat reflux. After the termination of the reaction, the solvent was distilled off under reduced pressure to obtain a liquid containing (E)-3- dimethylamino1-(4-(trifluoromethyl)pyrimidin-2-yl)-2-buten-1-one.

(2) 10 ml of acetic acid and 229 mg of 3-amino-1 H-1 ,2,4-triazole were added to the full amount of the liquid obtained in (1) containing (E)-3-dimethylamino-1-(4- (trifluoromethyl)pyrimidin-2-yl)-2-buten-1 -one, and the mixture was stirred for 2 hours at 100⁰C. After the termination of the reaction, the solvent was distilled off under reduced pressure, and water was added to the obtained residue, and extraction was carried out with ethyl acetate. The organic layer was washed with saturated sodium hydrogen carbonate aqueous solution and dried with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: methanol/ethyl acetate=1/3) to obtain 140 mg of the desired product. PREPARATION EXAMPLE 2 Preparation of 5-cyclopropyl-7-(1 -methyl-3-(trifluoromethyl)-1 H-pyrazol-5-yl)- [1 ,2,4]triazolo[1 ,5-a]pyrimidine (compound No.3)

(1) 161 mg of sodium ethoxide was added to a mixture of 350 mg of ethyl 1- methyl-3-(trifluoromethyl)-1 H-pyrazole-5-carboxylate, 400 mg of cyclopropyl methyl ketone and 3.5 ml of anhydrous tetrahydrofuran under stirring at about 60°C, and after the termination of the addition, the resulting solution was stirred for 50 minutes at the same temperature. After the termination of the reaction, the reaction mixture was cooled to room temperature, 1 N hydrochloric acid was added to the reaction mixture so as to be acidic, and extraction was carried out with ethyl acetate. The organic layer was washed with saturated salt solution and dried with anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/9) to obtain 181 mg of the oily 1-cyclopropyl-3-(1-methyl-3-(trifluoromethyl)-1 H-pyrazol-5- yl)propan-1 ,3-dione. NMR spectrum data of the obtained product is shown below. 1H-NMR δppm (solvent: CDCI₃ /400MHz ) 1.03(m,2H), 1.24(m,2H), 1.70(m,1 H), 4.23(s,3H), 6.09(s,1 H), 6.92(s,3H)

(2) 5 ml of acetic acid and 118 mg of 3-amino-1 H-1 ,2,4-triazole were added to 181 mg of 1-cyclopropyl-3-(1-methyl-3-(trifluoromethyl)-1 H-pyrazol-5-yl)propane-1 ,3- dione, a mixture was stirred for 3 hours under refulx, and then 118 mg of 3-amino-1 H- 1 ,2,4-triazole was added to the mixture, followed by stirring for 24 hours under heat reflux. After the termination of the reaction, the reaction mixture was cooled to room temperature, water was added to the reaction mixture, and then extraction was caried out with ethyl acetate. The organic layer was washed with a saturated sodium hydrogen carbonate aqueous solution and a saturated salt solution and dried with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=2/1 ) to obtain 117 mg of the desired product.

Typical examples of the compound of the formula (I) are shown in Table 1. In Table 1 , No. represents the compound No., Me methyl, Et ethyl, i-Pr isopropyl and Ph phenyl, and the temperature shown as the physical properties is the melting point. These compounds can be synthesized based on the synthesis examples 1 and 2 or various production process of the compounds of the present invention.

Now, Test Examples will be described. TEST EXAMPLE 1 Test on controlling effects against green peach aphid (Mvzus persicae)

A Japanese radish leaf was inserted in a test tube in which water was put, and about 20 first instar nymphs of green peach aphid were released on the leaf. On the next day, the number of nymphs parasitic on the leaf was counted, and then the leaf was dipped for about 10 seconds in an insecticidal solution adjusted to bring the concentration of the compound of the present invention to 200 ppm, dried in air and left in a constant temperature chamber at 25°C with lightening. The number of dead nymphs were counted 5 days after the treatment, and the mortality was calculated by the following equation. The insects dropped from the leaf or presented toxic symptom were counted as dead insects. The test was carried out with respect to the above- mentioned compound Nos. 3, 4, 24, 54 and 68, whereby all compounds showed a mortality of at least 90%. Mortality (%)=(1 -(number of survived insects/number of treated insects))x100

TEST EXAMPLE 2 Test on controlling effects against brown planthopper (Nilaparvata luqens)

Rice seedling was dipped for about 10 seconds in an insecticidal solution adjusted to bring the concentration of the compound of the present invention to 200 ppm and then dried in air, its root was wrapped with a wet absorbent cotton, and the seedling was put into a test tube. Then, 10 second-third instar nymphs of brown planthopper were released therein, and the test tube was covered with a gauze and left in a constant temperature chamber at 25°C with lightening. On the 5th day after the release, the number of dead nymphs were counted, and the mortality was calculated by the following equation.

The test was carried out with respect to the above-mentioned Compound Nos. 1 , 3, 4, 5, 6, 24, 26, 28, 50, 54, 57, 62, 66, 68 and 73, whereby all compounds showed a mortality of at least 90%.

Mortality (%)=(number of dead insects/number of released insects)x100 TEST EXAMPLE 3

Test on controlling effects against silverleaf whitefly (Bemisia arqentifoliO

An insecticidal solution adjusted to bring the concentration of the compound of the present invention to 200 ppm was applied by a hand spray to cucumber seedling planted in a pot on which first-second instar nymphs of silverleaf whitefly were parasitic, and dried in air. Thereafter, the cucumber seedling was left in a constant temperature chamber at 25°C with lightening. The number of old instar nymphs was counted 10 days after the treatment, and the protective value (%) was obtained by the following equation. The test was carried out with respect to the above-mentioned compound Nos. 3, 4, 22, 24, 26, 28, 50, 54, 65, 66 and 68, whereby all the compounds showed a protective value of at least 80%.

Protective value (%) = (1-((TaxCb)/(TbxCa)))x100

Ta: The number of old instar nymphs after the treatment at the treated cucumber seedling

Tb: The number of first-second instar nymphs before the treatment at the treated cucumber seedling

Ca: The number of old instar nymphs after the treatment at the untreated cucumber seedling

Cb: The number of first-second instar nymphs before the treatment at the untreated cucumber seedling

TEST EXAMPLE 4

Pesticidal test against Haemaphvsalis lonqicornis employing a dog

A gelatin capsule containing the compound of the present invention at a dose of 10 mg/kg weight is applied to a dog (Beagle, 8 months old), and immediately after the application, about 50 young mites of Haemaphvsalis longicornis are released on the auricle of the dog and artificially parasitized. After the treatment, observation is carried out to inspect the parasitic number, the fallen number and the mortality of the fallen Haemaphvsalis lonqicornis. As a result, the compound of the present invention is effective to have the parasitized Haemaphvsalis lonqicornis fallen or dead.

TEST EXAMPLE 5

Pesticidal test against cat flea (Ctenocephalides felis) employing a dog

A gelatin capsule containing the compound of the present invention at a dose of

10 mg/kg weight is applied to a dog (Beagle, 8 months old), and immediately after the application, about 100 non-bloodsucked adults of cat flea are released on the dorsal fur of the dog and artificially parasitized. The compound of the present invention shows an inhibitory effect for hatching on eggs laid by treated adults. Now, Formulation Examples are described below.

FORMULATION EXAMPLE 1 (1) Compound of the present invention 20 parts by weight

(2) Clay . 70 parts by weight

(3) White carbon 5 parts by weight

(4) Sodium polycarboxylate 3 parts by weight

(5) Sodium alkylnaphthalene sulfonate 2 parts by weight The above components are uniformly mixed and pulverized to obtain a wettable powder.

FORMULATION EXAMPLE 2

(1) Compound of the present invention 5 parts by weight

(2) Clay 60 parts by weight (3) Calcium carbonate 34.5 parts by weight

(4) Liquid paraffin 0.5 part by weight The above components are uniformly mixed to obtain a dust. FORMULATION EXAMPLE 3

(1) Compound of the present invention 20 parts by weight (2) N,N-dimethylacetamide 20 parts by weight

(3) Polyoxyethylene tristyryl phenyl ether 10 parts by weight

(4) Calcium dodecylbenzene sulfonate 2 parts by weight

(5) Xylene 48 parts by weight The above components are uniformly mixed and dissolved to obtain an emulsifiable concentrate.

FORMULATION EXAMPLE 4

(1 ) Clay 68 parts by weight

(2) Sodium lignin sulfonate 2 parts by weight

(3) Polyoxyethylenealkylaryl sulfate 5 parts by weight (4) White carbon 25 parts by weight

The mixture of the above components is mixed and pulverized with compound of the present invention in a weight ratio of 4:1 to obtain a wettable powder. FORMULATION EXAMPLE 5

(1) Compound of the present invention 50 parts by weight

(2) Condensate of sodium alkylnaphthalene sulfonate with formaldehyde

2 parts by weight (3) Silicone oil 0.2 part by weight

(4) Water 47.8 parts by weight The above components are uniformly mixed and pulverized to obtain a base liquid, and

(5) Sodium polycarboxylate 5 parts by weight (6) Anhydrous sodium sulfate 42.8 parts by weight are added, and the mixture is uniformly mixed, granulated and dried to obtain water-dispersible granules. FORMULATION EXAMPLE 6

(1) Compound of the present invention 5 parts by weight (2) Polyoxyethyleneoctylphenyl ether 1 part by weight

(3) Polyoxyethylene alkyl ether phosphoric acid ester 0.1 part by weight

(4) Granular calcium carbonate 93.9 parts by weight The above components (1) to (3) are preliminarily uniformly mixed and diluted with a proper amount of acetone, and then the mixture is sprayed onto the component (4), and acetone is removed to obtain granules. FORMULATION EXAMPLE 7

(1) Compound of the present invention 2.5 parts by weight

(2) N,N-dimethylacetamide 2.5 parts by weight

(3) Seed oil methyl ester 95.0 parts by weight The above components are uniformly mixed and dissolved to obtain an ultra low volume formulation. FORMULATION EXAMPLE 8

(1) Compound of the present invention 40 parts by weight

(2) Potassium polyoxyethylene tristyryl phenyl ether phosphate 4 parts by weight

(3) Silicone oil 0.2 part by weight

(4) Xanthan gum 0.1 part by weight

(5) Ethylene glycol 5 parts by weight

(6) Water 50.7 parts by weight 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 (3) Polyoxyethylenealkyl ether 10 parts by weight

The above components are uniformly mixed to obtain a soluble concentrate. FORMULATION EXAMPLE 10

(1 ) Compound of the present invention 40 parts by weight

(2) Condensate of sodium alkylnaphthalene sulfonate with formaldehyde 5 parts by weight

(3) Dioctyl sodium sulfosuccinate 1 part by weight

(4) Lactose 54 parts by weight The above components are uniformly mixed and pulverized, and then water is added and mixed. The mixture is granulated, dried and dressed to obtain water soluble granules.

The entire disclosure of Japanese Patent Application No. 2009-017716 filed on January 29, 2009 including specification, claims and summary is incorporated herein by reference in its entirety.

Claims

CLAIMS A triazolopyrimidine derivative represented by the formula (I) or its salt:

Het1 \ Het2 ^% Het3 v Het4

Het5 Het6 Het7

A is halogen, OR², alkyl or cycloalkyl; R² is hydrogen, alkyl, haloalkyl, alkoxy or NR³R⁴; R³ is hydrogen or alkyl; R⁴ is hydrogen, alkyl, haloalkyl, alkylcarbonyl, alkoxycarbonyl, haloalkylcarbonyl or haloalkoxycarbonyl; X is alkyl, alkenyl, alkynyl, aryl, halogen, haloalkyl, cyano, nitro, NR³R⁴, S(O)_nR³, OR² or COR²; Y is oxygen, sulfur or NR⁵; R⁵ is alkyl, haloalkyl, cycloalkyl or aryl; n is an integer of from O to 2; w¹ is an integer of from 1 to 3; w² is an integer of from 1 to 2; and in a case where w¹ or w² is at least 2, a plurality of X may be the same or different, 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.

2. The triazolopyrimidine derivative or its salt according to Claim 1 , wherein R¹ is alkyl which may be substituted by A, cycloalkyl which may be substituted by A, halogen, cyano, S(O)_nR³ or NR³R⁴.

3. A pesticide containing the triazolopyrimidine derivative or its salt as defined in Claim 1 , as an active ingredient.

4. An agricultural and horticultural pesticide containing the triazolopyrimidine derivative or its salt as defined in Claim 1 , as an active ingredient.

5. An insecticide, miticide, nematicide or soil pesticide containing the triazolopyrimidine derivative or its salt as defined in Claim 1 , as an active ingredient.

6. An insecticide or miticide containing the triazolopyrimidine derivative or its salt as defined in Claim 1 , as an active ingredient.

7. A method for controlling a pest, which comprises applying an effective amount of the triazolopyrimidine derivative or its salt as defined in Claim 1.

8. A process for producing a triazolopyrimidine derivative represented by the formula (I) or its salt:

Het5 _% Het6 Het7

A is halogen, OR², alkyl or cycloalkyl; R² is hydrogen, alkyl, haloalkyl, alkoxy or NR³R⁴; R³ is hydrogen or alkyl; R⁴ is hydrogen, alkyl, haloalkyl, alkylcarbonyl, alkoxycarbonyl, haloalkylcarbonyl or haloalkoxycarbonyl; X is alkyl, alkenyl, alkynyl, aryl, halogen, haloalkyl, cyano, nitro, NR³R⁴, S(O)_nR³, OR² or COR²; Y is oxygen, sulfur or NR⁵; R⁵ is alkyl, haloalkyl, cycloalkyl or aryl; n is an integer of from O to 2; w¹ is an integer of from 1 to 3; w² is an integer of from 1 to 2; and in a case where W¹ or W² is at least 2, X may be the same or different, 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, which comprises (1) condensing an α,β-unsaturated ketone derivative represented by the formula (IV):

wherein R^1a is alkyl which may be substituted by A¹, cycloalkyl which may be substituted by A¹, alkenyl which may be substituted by A¹, alkynyl which may be substituted by A¹ or aryl; A¹ is OR^2a, alkyl or cycloalkyl; R^2a is hydrogen, alkyl or haloalkyl; R⁷ is alkyl; and Het is as defined above, with a compound represented by the formula (V),

(2) condensing an α,β-unsaturated ketone derivative represented by the formula (VII):

wherein R^3a is alkyl; and Het is as defined above, with a compound represented by the formula (V),

(3) oxidizing a compound represented by the formula (1-2):

wherein Het and R^3a are as defined above,

(4) reacting a compound represented by the formula (1-3):

wherein Het and R^3a are as defined above; and na is an integer of 1 or 2, with a nucleophilic reagent,

(5) condensing a compound represented by the formula (IX)

wherein R^1c is alkyl which may be substituted by A¹, cycloalkyl which may be substituted by A¹, alkenyl which may be substituted by A¹, alkynyl which may be substituted by A¹, or aryl; and A¹ and Het are as defined above, with a compound represented by the formula (V), or

(6) reacting a triazolopyrimidine derivative represented by the formula (XIV):

wherein R^1d is alkyl which may be substituted by A, cycloalkyl which may be substituted by A, alkenyl which may be substituted by A, alkynyl which may be substituted by A, or aryl; Q¹ is halogen; and A is as defined above, with a compound represented by the formula (XV): Het-B(R¹³)_P wherein R¹³ is OH, alkyl, cycloalkyl, alkoxy or fluorine; in a case where R¹³ is OH, alkyl, cycloalkyl or alkoxy, p is 2; in a case where R¹³ is fluorine, p is 3; the alkyl or alkoxy for R¹³ may bond each other to form a ring together with the adjacent boron atom; and Het is as defined above.