WO2010018853A1 - Pyridyl-triazolopyrimidine derivative or salt thereof, and harmful organism control agent comprising the same - Google Patents

Abstract

Disclosed is a novel harmful organism control agent. The harmful organism control agent comprises a pyridyl-triazolopyrimidine derivative represented by formula (I) [wherein R¹ represents an optionally substituted alkyl, an optionally substituted cycloalkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, a halogen atom, a cyano, an aryl, an optionally alkyl-substituted heterocyclic group, CH=NOR², CH=NNR⁴R⁵, COR², COOR², OR², S(O)_nR³, NR⁴R⁵ or CONR⁴R⁵; X represents an alkyl, an alkenyl, an alkynyl, an aryl, a heterocyclic group, a halogen atom, a haloalkyl, a cyano, a nitro, NR⁴R⁵, CONR⁴R⁵, S(O)_nR³, OR², COR² or COOR²; m represents an integer of 1 to 4; and n represents an integer of 0 to 2] or a salt thereof as an active ingredient.

Description

Pyridyl-triazolopyrimidine derivatives or salts thereof, and pest control agents containing them

The present invention relates to a pest control agent containing a novel pyridyl-triazolopyrimidine derivative or a salt thereof as an active ingredient.

Patent Document 1 discloses the use of a triazolopyrimidine derivative having a specific chemical structure as a nematicide. However, these compounds differ in chemical structure from the compounds of the present invention. Patent Document 2 discloses a method for inhibiting or treating cancerous tumor cell proliferation and related diseases by administering an effective amount of a triazolopyrimidine derivative to a mammal. However, there is no description of the compounds of the present invention and the use of the compounds of the present invention as pest control agents.

International Publication Gazette WO2004 / 083383 International Publication WO2002 / 02563

Over the years, many pest control agents have been used, but many have various problems such as insufficient efficacy, pests gaining resistance and their use being restricted. Therefore, development of a new pest control agent with few such disadvantages, for example, a pest control agent capable of controlling various pests that are problematic in the field of agriculture and horticulture and pests parasitic on animals is desired.

The present inventors have made various studies on pyridyl-triazolopyrimidine derivatives in order to find better pest control agents. As a result, it was found that the novel pyridyl-triazolopyrimidine derivative has a very high control effect against pests at a low dosage, and also has safety against crops, pest natural enemies or mammals. The present invention has been completed.

That is, the present invention relates to the formula (I):

[Wherein R ¹ is alkyl optionally substituted with A, cycloalkyl optionally substituted with A, alkenyl optionally substituted with A, alkynyl optionally substituted with A, halogen atom, cyano, aryl , A heterocyclic group which may be substituted with alkyl, CH═NOR ² , CH═NNR ⁴ R ⁵ , COR ² , COOR ² , OR ² , S (O) _n R ³ , NR ⁴ R ⁵ or CONR ⁴ R ⁵ X is alkyl, alkenyl, alkynyl, aryl, heterocyclic group, halogen atom, haloalkyl, cyano, nitro, NR ⁴ R ⁵ , CONR ⁴ R ⁵ , S (O) _n R ³ , OR ² , COR ² or COOR ² ; A is a halogen atom, OR ² , S (O) _n R ³ , OS (O) _n R ³ , NR ⁴ R ⁵ , cyano, alkyl, cycloalkyl, aryl, heterocyclic group, SCH ₂ COOR ² , NHNR ⁴ R ⁵ , C OOR ² , nitro or —CH (CN) ₂ ; R ² is a hydrogen atom, alkyl, alkenyl, alkynyl, haloalkyl, cyanoalkyl, alkoxyalkyl, acetyl, benzyl or aryl; R ³ is alkyl or acetyl R ⁴ is a hydrogen atom or alkyl; R ⁵ is a hydrogen atom, alkyl, cycloalkyl, haloalkyl, COR ² , COOR ² , S (O) _n R ³ , CH ₂ CH ₂ OR ² or CH ₂ CN. M is an integer of 1 to 4; n is an integer of 0 to 2], or a salt thereof.
The present invention also relates to a pest control agent comprising a pyridyl-triazolopyrimidine derivative of the formula (I) or a salt thereof as an active ingredient.

The pest control agent comprising the pyridyl-triazolopyrimidine derivative of the formula (I) or a salt thereof as an active ingredient has a very high control effect against pests with a low dose.

When m in the formula (I) is an integer of 2 to 4, each X may be the same or different.
Examples of the halogen atom in the formula (I) or the halogen atom as a substituent include each atom of fluorine, chlorine, bromine or iodine. The number of halogen atoms as a substituent may be 1 or 2 or more, and in the case of 2 or more, each halogen atom may be the same or different. Further, the halogen atom may be substituted at any position.
The alkyl in the formula (I) may be linear or branched, and specific examples thereof include C ₁ such as methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, hexyl. _-6 and so on.
Examples of cycloalkyl in formula (I) include C _3-6 such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

The alkenyl in the formula (I) may be linear or branched, and specific examples thereof include vinyl, 1-propenyl, allyl, isopropenyl, 1-butenyl, 1,3-butadienyl, -C _2-6 such as hexenyl.
The alkynyl in the formula (I) may be linear or branched, and specific examples thereof include ethynyl, 2-butynyl, 2-pentynyl, 3-methyl-1-butynyl, 2-pentene- Examples thereof include C _2-6 such as 4-ynyl and 3-hexynyl.
Examples of the aryl in the formula (I) include C _6-10 aryl such as phenyl and naphthyl.

The heterocyclic group in the formula (I) includes a condensed heterocyclic group in addition to a monocyclic heterocyclic group. The monocyclic heterocyclic group includes, for example, a 3-membered heterocyclic group such as oxiranyl; furyl, tetrahydrofuryl, thienyl, pyrrolyl, pyrrolinyl, pyrrolidinyl, dioxolanyl, oxazolyl, oxazolinyl, isoxazolyl, thiazolyl, thiazolinyl, isothiazolyl, imidazolyl, imidazolinyl 5-membered heterocyclic groups such as imidazolidinyl, oxazolidinyl, oxazolidinyl, thiazolidinyl, pyrazolyl, pyrazolinyl, pyrazolidinyl, triazolyl, oxadiazolyl, thiadiazolyl, tetrazolyl; And 6-membered heterocyclic groups such as triazinyl. Among these monocyclic heterocyclic groups, a 5- or 6-membered heterocyclic group containing 1 to 4 atoms of at least one atom selected from the group consisting of O, S and N is desirable. Examples of the condensed heterocyclic group include benzofuranyl, isobenzofuranyl, dihydrobenzofuranyl, dihydroisobenzofuranyl, benzothienyl, isobenzothienyl, dihydrobenzothienyl, dihydroisobenzothienyl, tetrahydrobenzothienyl, indolyl, isoindolyl, Benzoxazolyl, benzothiazolyl, indazolyl, benzimidazolyl, benzodioxolanyl, benzodioxanyl, chromenyl, chromanyl, isochromanyl, chromonyl, chromanonyl, quinolyl, isoquinolyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, indolizinyl, quinolizylyl , Naphthyridinyl, pteridinyl, dihydrobenzoxazinyl, dihydrobenzoxazolinonyl, dihydride Benzoxadiazoles nonyl, benzothiadiazole oxa sulfonyl and the like. Among these condensed heterocyclic groups, 8- to 10-membered condensed heterocyclic groups containing 1 to 4 at least one atom selected from the group consisting of O, S and N are desirable.

The salt of the pyridyl-triazolopyrimidine derivative of the formula (I) includes any agriculturally acceptable salt. Examples thereof include ammonium salts such as dimethylammonium salt and triethylammonium salt; hydrochloride Inorganic acid salts such as perchlorate, sulfate and nitrate; organic acid salts such as acetate and methanesulfonate.

The pyridyl-triazolopyrimidine derivative of the formula (I) may have isomers such as optical isomers and geometric isomers, but the present invention includes both isomers and isomer mixtures. It is. In the present specification, unless otherwise specified, isomers are described as a mixture. The present invention also includes various isomers other than those described above within the scope of technical common sense in the technical field. Depending on the type of isomer, there may be a chemical structure different from that of the formula (I). However, since those skilled in the art can fully recognize that they are related to isomers, the scope of the present invention. It is clear that it is within.

The pyridyl-triazolopyrimidine derivative of the formula (I) or a salt thereof can be produced according to the following production methods [1] to [9] and usual salt production methods, and is also produced according to the synthesis examples described later. be able to.
Manufacturing method [1]

PRODUCTION PROCESS [1], R ^1a is optionally substituted by by alkyl which may be, cycloalkyl which may be substituted by A ^1, alkenyl which may be substituted by A ^1, A ¹ substituted by A ¹ alkynyl, A heterocyclic group which may be substituted with aryl or alkyl; A ¹ is a halogen atom, OR ^2a , S (O) _n R ³ , NR ⁴ R ^5a , cyano, alkyl, cycloalkyl, aryl, heterocyclic group , SCH ₂ COOR ^2a , NHNR ⁴ R ^5a or —CH (CN) ₂ ; R ^2a is a hydrogen atom, alkyl, alkenyl, alkynyl, haloalkyl, alkoxyalkyl, acetyl, benzyl or aryl; R ^5a is a hydrogen atom , alkyl, cycloalkyl, haloalkyl, COR ^2a, be COOR ^2a or ^{_{S (O) n R 3;}} R 6 and ^{R 7} each independently is ^{alkyl; R 3, R 4, X} , m Fine n are as defined above.

In the production method [1], the compound of the formula (II) and the compound of the formula (III) are condensed to obtain the α, β-unsaturated ketone derivative of the formula (IV), the reaction of the formula (IV) The latter reaction consists of condensing the compound with the compound of formula (V) to obtain the [1,2,4] triazolo [1,5-a] pyrimidine derivative of formula (I-1).

Production Method [1] In the first half of the reaction, the compound of formula (III) can be used at a ratio of 0.8 to 5 equivalents, preferably 1 to 3.5 equivalents, per 1 mol of the compound of formula (II). This reaction can be performed in the presence of a solvent, if necessary. Any solvent may be used as long as it is inert to the reaction. For example, alcohols such as methanol, ethanol, propanol and butanol; aromatic hydrocarbons such as benzene, toluene and xylene; pentane, hexane, heptane, Aliphatic hydrocarbons such as petroleum ether, ligroin and petroleum benzine; ethers such as diethyl ether, dipropyl ether, dibutyl ether, tetrahydrofuran and dioxane; esters such as methyl acetate and ethyl acetate; acetonitrile, propionitrile and the like Nitriles; acid amides such as N, N-dimethylformamide, N, N-dimethylacetamide and N-methylpyrrolidinone; sulfoxides such as dimethyl sulfoxide; sulfones such as sulfolane; hexamethyl phosphorami Phosphoric acid amides such as; may be mentioned, and a mixed solvent thereof; chloroform, dichloromethane, carbon tetrachloride, halogenated hydrocarbons such as 1,2-dichloroethane. The reaction temperature is usually from 80 to 200 ° C, preferably from 100 to 150 ° C. The reaction time is usually 2 to 48 hours.

Production Method [1] In the latter half of the reaction, the compound of formula (V) can be used in a proportion of 0.8 to 10 equivalents, preferably 1 to 2.5 equivalents, relative to 1 mol of the compound of formula (IV). This reaction can be performed in the presence of a solvent, if necessary. Any solvent may be used as long as it is inert to the reaction, for example, carboxylic acids such as acetic acid and propionic acid; alcohols such as methanol, ethanol, propanol and butanol; aromatic carbonization such as benzene, toluene and xylene. Hydrogen: aliphatic hydrocarbons such as pentane, hexane, heptane, petroleum ether, ligroin, petroleum benzine; ethers such as diethyl ether, dipropyl ether, dibutyl ether, tetrahydrofuran, dioxane; esters such as methyl acetate and ethyl acetate Nitriles such as acetonitrile and propionitrile; acid amides such as N, N-dimethylformamide, N, N-dimethylacetamide and N-methylpyrrolidinone; sulfoxides such as dimethyl sulfoxide; sulfolane and the like Examples include sulfones; phosphoric acid amides such as hexamethylphosphoramide; halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride, and 1,2-dichloroethane; and mixed solvents thereof. Acids are desirable. The reaction temperature is usually 50 to 150 ° C., desirably 80 to 120 ° C. The reaction time is usually 0.5 to 100 hours.
Manufacturing method [2]

PRODUCTION PROCESS [2], Y is a halogen atom, R ^{3, X} and m are as defined above. Examples of the halogen atom for Y include fluorine, chlorine, bromine and iodine atoms.

The production method [2] includes a reaction in the first half to obtain an α, β-unsaturated ketone derivative of the formula (VII) by reacting a compound of the formula (II), carbon disulfide and a compound of the formula (VI). The latter reaction consists of condensing the compound of formula (VII) with the compound of formula (V) to obtain the [1,2,4] triazolo [1,5-a] pyrimidine derivative of formula (I-2).

Production method [2] In the first half of the reaction, carbon disulfide and the compound of formula (VI) are used in an amount of 0.8 to 5 equivalents, preferably 1 to 3 equivalents, per 1 mol of the compound of formula (II). it can. In this reaction, the compound of formula (VII) can be produced by reacting in the presence of a base and a solvent. Examples of the base include alkali metal hydrides such as sodium hydride and potassium hydride; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metals such as sodium and potassium; sodium methoxide and sodium Ethoxide, alkali metal alkoxides such as potassium tertiary butoxide; and the like. The base can be used in an amount of 1 to 10 equivalents, preferably 1 to 3 equivalents, relative to 1 mol of the compound of formula (II). The solvent may be any solvent as long as it is inert to the reaction, and examples thereof include the same ones as in the reaction in the first half of the production method [1]. The reaction temperature is usually 0 to 100 ° C., preferably 10 to 50 ° C. The reaction time is usually 6 to 48 hours.

Production method [2] In the latter half of the reaction, the compound of the formula (V) can be used in a proportion of 0.8 to 5 equivalents, preferably 1 to 3 equivalents, relative to 1 mol of the compound of the formula (VII). This reaction can be performed in the presence of a base and a solvent, if necessary. Examples of the base include alkali metal hydrides such as sodium hydride and potassium hydride; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metals such as sodium and potassium; sodium methoxide and sodium Alkali metal alkoxides such as ethoxide and potassium tertiary butoxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; alkali metal bicarbonates such as sodium bicarbonate and potassium bicarbonate; such as triethylamine and pyridine Organic bases; and the like. The base can be used in an amount of 1 to 5 equivalents, preferably 1 to 3 equivalents, relative to 1 mol of the compound of formula (V). The solvent may be any solvent as long as it is inert to the reaction, and examples thereof include the same ones as in the reaction in the first half of the production method [1]. The reaction temperature is usually 100 to 200 ° C. The reaction time is usually 0.1 to 10 hours.
Manufacturing method [3]

In the production method [3], R ³ , X and m are as described above, and na is an integer of 1 to 2.

In the production method [3], the compound of formula (I-2) and an oxidizing agent are reacted in the presence of a solvent to thereby react [1,2,4] triazolo [1,5-a of formula (I-3). Pyrimidine derivatives can be produced.

Examples of the oxidizing agent used in the above reaction include hydrogen peroxide, peracetic acid, m-chloroperbenzoic acid, and the like. The solvent may be any solvent that is inert to the reaction, for example, halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride, and 1,2-dichloroethane; ketones such as acetone and dimethyl ethyl ketone; Mention may be made of ethers such as diethyl ether, dipropyl ether, dibutyl ether, tetrahydrofuran and dioxane; carboxylic acids such as acetic acid and propionic acid; and mixed solvents thereof. The oxidizing agent can be used in a ratio of 1 to 3 equivalents per 1 mol of the compound of the formula (I-2). The reaction temperature is usually room temperature to reflux temperature. The reaction time is usually 1 to 24 hours.
Manufacturing method [4]

PRODUCTION PROCESS [4], R ^1b is optionally substituted by by alkyl which may be, cycloalkyl which may be substituted by A ^1, alkenyl which may be substituted by A ^1, A ¹ substituted by A ¹ alkynyl, A halogen atom, cyano, aryl, an optionally substituted heterocyclic group, OR ^2a or NR ⁴ R ^5a ; R ^2a , R ⁴ , R ^5a , A ¹ , X and m are as defined above.

In the production method [4], the compound of the formula (I-3) is reacted with a nucleophile in the presence of a solvent to thereby react [1,2,4] triazolo [1,5- a] Pyrimidine derivatives can be produced.

Examples of the nucleophile include alkali metal alkoxides such as sodium methoxide and sodium ethoxide; alkali metal mercaptides such as sodium methyl mercaptan; primary or secondary amines such as methylamine, dimethylamine and piperidine; And organometallic reagents such as bromide, ethylmagnesium bromide, and phenylmagnesium bromide; fluorinating agents such as potassium fluoride, cesium fluoride, and tetrabutylammonium fluoride; The nucleophilic reagent can be used in a ratio of 1 to 5 equivalents, preferably 1 to 3 equivalents, relative to 1 mol of the compound of formula (I-3). Any solvent may be used as long as it is inert to the reaction. For example, alcohols such as methanol, ethanol, propanol and butanol; aromatic hydrocarbons such as benzene, toluene and xylene; pentane, hexane and heptane Aliphatic ethers such as petroleum ether, ligroin and petroleum benzine; ethers such as diethyl ether, dipropyl ether, dibutyl ether, tetrahydrofuran and dioxane; esters such as methyl acetate and ethyl acetate; acetonitrile, propionitrile and the like Nitriles; acid amides such as N, N-dimethylformamide, N, N-dimethylacetamide and N-methylpyrrolidinone; sulfoxides such as dimethyl sulfoxide; and mixed solvents thereof. The reaction temperature is usually −100 to 50 ° C., desirably −70 to 30 ° C. The reaction time is usually 1 minute to 48 hours.
Manufacturing method [5]

In the production process [5], R ⁸ is alkyl; R ^1a , X and m are as described above.

In the production method [5], the reaction of the first half to obtain the compound of the formula (IX) by reacting the compound of the formula (II) with the compound of the formula (VIII), the compound of the formula (IX) and the compound of the formula (V) The latter reaction consists of condensing the compound to obtain the [1,2,4] triazolo [1,5-a] pyrimidine derivative of formula (I-5).

Process [5] In the first half of the reaction, the compound of formula (VIII) can be used in a proportion of 0.8 equivalent to large excess, preferably 1 to 10 equivalents, relative to 1 mol of the compound of formula (II). In this reaction, the compound of formula (IX) can be produced by reacting in the presence of a base and a solvent. Examples of the base include those similar to the reaction in the first half of the above production method [2]. The base can be used in a proportion of 1 to 5 equivalents, preferably 1 to 2 equivalents, relative to the compound of formula (II). Any solvent may be used as long as it is inert to the reaction. For example, alcohols such as methanol, ethanol, propanol and butanol; aromatic hydrocarbons such as benzene, toluene and xylene; pentane, hexane, heptane, Aliphatic hydrocarbons such as petroleum ether, ligroin and petroleum benzine; ethers such as diethyl ether, dipropyl ether, dibutyl ether, tetrahydrofuran and dioxane; N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl Acid amides such as pyrrolidinone; sulfoxides such as dimethyl sulfoxide; sulfones such as sulfolane; halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride, 1,2-dichloroethane; and a mixed solvent thereof. You can gel, among others ethers are preferred. The reaction temperature is usually 0 to 70 ° C., preferably 10 to 50 ° C. The reaction time is usually 0.1 to 24 hours.

Production Method [5] In the latter half of the reaction, the compound of the formula (V) can be used in a proportion of 0.8 to 10 equivalents, preferably 1 to 2.5 equivalents, relative to 1 mol of the compound of the formula (IX). In this reaction, the compound of formula (I-5) can be produced in the presence of a solvent. The solvent may be any solvent as long as it is inert to the reaction, and examples thereof include the same ones as in the reaction in the latter half of the above production method [1]. Among them, carboxylic acids are preferable. In addition, when Formula (IX) is a liquid at normal temperature, after the reaction in the first half of the production method [5], the reaction in the latter half of the production method [5] can be carried out without isolating the compound. The reaction temperature is usually 50 to 150 ° C., desirably 80 to 120 ° C. The reaction time is usually 0.5 to 100 hours.
Manufacturing method [6]

In the production process [6], R ^1c is a halogen atom; R ⁹ and R ¹⁰ are each independently alkyl; X, Y, and m are as described above. Examples of the halogen atom for R ^1c include fluorine, chlorine and bromine atoms.

In the production method [6], the compound of the formula (I-6) can be produced by the reactions (a) to (e) above. Each reaction is described in detail below.

(a) The compound of the formula (XII) can be produced by reacting the compound of the formula (X) with the compound of the formula (XI) in the presence of a base and a solvent. The compound of the formula (XI) can be used in a proportion of 0.8 equivalent to a large excess, desirably 1 to 30 equivalent, relative to 1 mol of the compound of the formula (X). Examples of the base include those similar to the reaction in the first half of the above production method [2]. The base can be used at a ratio of 1 to 5 equivalents, preferably 1 to 2 equivalents, relative to 1 mol of the compound of the formula (X). The solvent may be any solvent as long as it is inert to the reaction, and examples thereof include those similar to the reaction in the first half of the above production method [5]. Among them, ethers are desirable. The reaction temperature is usually 0 to 70 ° C., preferably 10 to 50 ° C. The reaction time is usually 0.1 to 24 hours.

(b) The compound of the formula (XIII) can be produced by hydrolyzing the compound of the formula (XII) in the presence of a base and water. Examples of the base include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide. The base can be used in a proportion of 1 equivalent to a large excess with respect to the compound of the formula (XII). The reaction temperature is usually 0 to 70 ° C., preferably 10 to 50 ° C. The reaction time is usually 0.1 to 24 hours.

(c) The compound of formula (XIV) can be produced by reacting the compound of formula (XIII) with a halogenating agent in the presence of a solvent. Examples of the halogenating agent include thionyl chloride and oxalyl dichloride. The halogenating agent can be used in a proportion of 1 to 5 equivalents, preferably 1 to 2 equivalents, relative to 1 mol of the compound of the formula (XIII). The solvent may be any solvent that is inert to the reaction, and examples thereof include halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride, and 1,2-dichloroethane. The reaction temperature is usually 0 to 100 ° C., preferably 10 to 50 ° C. The reaction time is usually 0.1 to 24 hours.

(d) 4,5-dihydro-5-oxo [1,2,4] triazolo [1,5-a] pyrimidine derivative of formula (XV) is a compound of formula (XIV) and a compound of formula (V) Can be produced by condensation. The compound of the formula (V) can be used in a ratio of 0.8 to 10 equivalents, desirably 1 to 2.5 equivalents, relative to 1 mol of the compound of the formula (XIV). This reaction can be performed in the presence of a solvent, if necessary. Any solvent may be used as long as it is inert to the reaction. For example, the same reaction as in the first half of the above production method [5] can be mentioned, but acid amides are particularly desirable. The reaction temperature is usually 0 to 150 ° C., preferably 20 to 100 ° C. The reaction time is usually 0.5 to 100 hours.

(e) The 5-halo [1,2,4] triazolo [1,5-a] pyrimidine derivative of formula (I-6) is produced by reacting the compound of compound (XV) with a halogenating agent. be able to. Examples of the halogenating agent include thionyl chloride, phosphorus oxychloride, phosphorus oxybromide and the like. The halogenating agent can be used in a proportion of 1 to 20 equivalents, preferably 1 to 8 equivalents, relative to 1 mol of the compound of the formula (XV). This reaction can be performed in the presence of a solvent, if necessary. The solvent may be any solvent that is inert to the reaction, and examples thereof include halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride, 1,2-dichloroethane. The reaction temperature is usually 0 to 150 ° C., preferably 20 to 100 ° C. The reaction time is usually 0.1 to 24 hours.
Manufacturing method [7]

In the production method [7], R ⁹ , R ^1a , X and m are as described above.

In the production method [7], the compound of formula (X) is reacted with the compound of formula (XVI) to obtain the compound of formula (IX), and the compound of formula (IX) and formula (V) The latter reaction consists of condensing the compound to obtain the [1,2,4] triazolo [1,5-a] pyrimidine derivative of formula (I-5).

Production Method [7] In the first half of the reaction, the compound of the formula (XVI) can be used in a proportion of 0.8 equivalent to a large excess, preferably 1 to 10 equivalents, relative to 1 mol of the compound of the formula (X). In this reaction, the compound of formula (IX) can be produced in the presence of a base and a solvent. Examples of the base include those similar to the reaction in the first half of the above production method [5]. The base can be used at a ratio of 1 to 5 equivalents, preferably 1 to 2 equivalents, relative to 1 mol of the compound of the formula (X). The solvent may be any solvent as long as it is inert to the reaction, and examples thereof include those similar to the reaction in the first half of the above production method [5]. Among them, ethers are desirable. The reaction temperature is usually 0 to 70 ° C., preferably 10 to 50 ° C. The reaction time is usually 0.1 to 24 hours.
The reaction in the latter half of the production process [7] can be carried out in the same manner as the reaction in the latter half of the production process [5]. Manufacturing method [8]

In the production process [8], R ¹¹ and R ¹² are each independently hydrogen, alkyl or cycloalkyl; X, Y and m are as described above.

In the production method [8], the compound of the formula (I-7) and the halogenating agent are reacted in the presence of a solvent and a small amount of a radical initiator to thereby produce [1,2,4 of the formula (I-8). ] A triazolo [1,5-a] pyrimidine derivative can be produced. This reaction can be performed under light irradiation as needed.

Examples of the halogenating agent include N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide and the like. The halogenating agent can be used in a proportion of 1 to 5 equivalents, preferably 1 to 2 equivalents, relative to the compound of formula (I-7). Examples of the radical initiator include benzoyl peroxide and azobisisobutyronitrile. Any solvent may be used as long as it is inert to the reaction. Examples thereof include halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride, and 1,2-dichloroethane. The reaction temperature is usually 0 to 100 ° C., preferably 10 to 80 ° C. The reaction time is usually 0.1 to 24 hours.
Manufacturing method [9]

PRODUCTION PROCESS [9], R ¹³ is optionally substituted by by alkyl which may be, cycloalkyl which may be substituted by A ^1, alkenyl which may be substituted by A ^1, A ¹ substituted by A ¹ alkynyl, A heterocyclic group which may be substituted with a halogen atom, cyano, aryl or alkyl, OR ¹⁴ , SR ¹⁴ or NR ¹⁵ R ¹⁶ , wherein R ¹⁴ , R ¹⁵ and R ¹⁶ may each independently be substituted with A ¹ ; alkyl, cycloalkyl which may be substituted by A ^1, is substituted with an alkenyl or A ¹ may be substituted by A ¹ be also good ^{alkynyl; R 11, R 12, A} 1, X and m are described above It is as follows.

In the production method [9], the compound of the formula (I-8) is reacted with a nucleophile in the presence of a solvent to give [1,2,4] triazolo [1,5- a] Pyrimidine derivatives can be produced.

Examples of nucleophiles include alkali metal alkoxides such as sodium methoxide and sodium ethoxide; alkali metal haloalkoxides such as sodium trifluoromethyl ethoxide; alkali metal mercaptides such as sodium methyl mercaptan; methylamine and dimethylamine Primary or secondary amines such as pyridine, piperidine, morpholine; organometallic reagents such as methylmagnesium bromide, ethylmagnesium bromide, phenylmagnesium bromide; fluorine such as potassium fluoride, cesium fluoride, tetrabutylammonium fluoride A cyanating agent such as potassium cyanide and sodium cyanide; and the like. The nucleophilic reagent can be used in a ratio of 1 to 5 equivalents, preferably 1 to 3 equivalents, relative to 1 mol of the compound of the formula (I-8). The solvent may be any solvent as long as it is inert to the reaction, and examples thereof include the same ones as in the reaction of the above production method [4]. The reaction temperature is usually −100 to 50 ° C., desirably −70 to 20 ° C. The reaction time is usually 6 to 48 hours.

Further, the following formula (I-10) which can be produced by the same production method as described in the above production method [1], production method [4], production method [5] or production method [7] or Synthesis Example 1 (1) to (2) described later ;

Wherein X ^a is alkyl, aryl, halogen atom, haloalkyl, cyano, nitro, OR ^2b , COR ^2b or COOR ^2b ; R ^2b is alkyl, alkenyl, alkynyl, haloalkyl, cyanoalkyl, alkoxyalkyl, acetyl, Benzyl or aryl; m is as described above), and one or more methods are appropriately selected from the same methods as those described in Synthesis Examples 1 to 13 below. By performing, the methyl group at the 5-position on the triazolopyrimidine ring can be appropriately converted to another substituent selected from R ¹ . In addition, the following formula (I-11) which can be produced by the production method [1], the production method [4] or the production method [5] or the same method as in Synthesis Examples 14 (1) to (4) described later;

(Wherein, X ^a and m are as described above), and 5 5 on the triazolopyrimidine ring is prepared in the same manner as in Synthesis Example 14 (5) or Synthesis Example 15 described later. The 1-hydroxyethyl group at the position can be appropriately converted to another substituent selected from R ¹ .

Further, the above-mentioned production method [1], production method [4], production method [5], production method [7] or production method [9], or Synthesis Examples 1 (1) to (2), Synthesis Example 14 (1) to (2), Synthesis Example 14 (1) to (5), Synthesis Example 16 (1) to (5) or Synthesis Example 17 (1) to (2) or the following formula (I-12) ;

Wherein X ^b is alkyl, halogen atom, haloalkyl, cyano, OR ^2a , COOR ^2a acetyl, S (O) _n R ^3a , NR ⁴ R ^5a or CONR ⁴ R ^5b ; R ^3a is alkyl R ^1a , R ^2a , R ⁴ , R ^5a , m and n are as described above), and the synthesis examples 18 (1), 18 (2), and 18 A specific substituent on the pyridine ring can be appropriately converted to another substituent selected from X by appropriately selecting and executing one or more methods from the same methods as in Example 19. Further, the compound represented by the formula (I-12) may be selected from X by selecting a specific substituent on the pyridine ring by a known substituent conversion reaction in addition to the method similar to the synthesis example described later. Can be appropriately converted to the above substituent.

The desirable mode of the pest control agent containing the compound of the present invention is described below. The pest control agent containing the compound of the present invention includes, for example, various pest control agents that are problematic in the field of agriculture and horticulture, that is, agricultural and horticultural pest control agents, and pest control agents that parasitize animals, that is, animal parasitics. It is particularly useful as a biocontrol agent.

Pesticides for agricultural and horticultural use are useful, for example, as insecticides, acaricides, nematicides or soil insecticides. Plant parasitic mites such as rustic mites, mites, aphids such as peach aphids and cotton aphids; diamondback moths, weevil, scallops, codling moths, ball worms, tobacco worms, mai moths, yellow moths, prickly winged clams, Colorado Agricultural pests such as leaf beetle, cucumber beetle, ball weevil, leafhoppers, leafhoppers, scale insects, stink bugs, whitefly, thrips, grasshoppers, fly flies, scarab beetles, tamanayaga, kaburagaga, ants, etc .; Plant parasitic nematodes such as cucumbers, cyst nematodes, nesting nematodes, rice scented nematodes, strawberry nematodes, pine wood nematodes; gastropods such as slugs, maimai, etc .; Soil pests such as isopods; hygiene pests such as house dust mites, cockroaches, house flies, mosquitoes; storage pests such as bark moths, azuki beetles, bark beetles, bark beetles, bark beetles, etc .; It is effective for controlling clothes such as termites, house pests; indoor dust mites such as white mites, white leopard mites, and white ticks. The agricultural and horticultural pest control agent containing the compound of the present invention is particularly effective for controlling plant parasitic mites, agricultural pests, plant parasitic nematodes and the like. Among them, it is most useful as an insecticidal or acaricidal agent because it exhibits a further excellent effect in controlling plant parasitic mites and agricultural pests. Moreover, the agricultural and horticultural pesticide containing the compound of the present invention is also effective for controlling various resistant pests against drugs such as organic phosphorus agents, carbamate agents, and synthetic pyrethroid agents. Furthermore, since the compound of the present invention has excellent osmotic transfer properties, soil harmful insects, mites, nematodes by treating agricultural and horticultural pesticides containing the compound of the present invention on the soil It is possible to control pests on the foliage at the same time as the control of gastropods and isopods.

Another desirable embodiment of the pest control agent containing the compound of the present invention is a farm that comprehensively controls the aforementioned plant parasitic mites, agricultural pests, plant parasitic nematodes, gastropods, soil pests, etc. Examples include horticultural pest control agents.

The agricultural and horticultural pest control agent containing the compound of the present invention is usually a powder, granule, granule wettable powder, wettable powder, aqueous suspension, by mixing the compound with various agricultural adjuvants, Used in various forms such as oil suspensions, aqueous solvents, emulsions, solutions, pastes, aerosols, microdispersions, etc. It can be in any formulation form. Adjuvants used in the formulation include solid carriers such as diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, kaolin, bentonite, kaolinite, sericite, clay, sodium carbonate, sodium bicarbonate, sodium sulfate, zeolite, starch; water , Toluene, xylene, solvent naphtha, dioxane, acetone, isophorone, methyl isobutyl ketone, chlorobenzene, cyclohexane, dimethyl sulfoxide, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, alcohol, etc. Solvent; fatty acid salt, benzoate, alkylsulfosuccinate, dialkylsulfosuccinate, polycarboxylate, alkylsulfate, alkylsulfate, alkylarylsulfate, alkyldiglycolethersulfate, al Cole sulfate ester salt, alkyl sulfonate salt, alkyl aryl sulfonate salt, aryl sulfonate salt, lignin sulfonate salt, alkyl diphenyl ether disulfonate salt, polystyrene sulfonate salt, alkyl phosphate ester salt, alkyl aryl phosphate salt, styryl Aryl phosphate, polyoxyethylene alkyl ether sulfate, polyoxyethylene alkyl aryl ether sulfate, polyoxyethylene alkyl aryl ether sulfate, polyoxyethylene alkyl ether phosphate, polyoxyethylene alkyl aryl phosphate Salts, anionic surfactants such as salt of naphthalenesulfonic acid formalin condensate; sorbitan fatty acid ester, glycerin fatty acid ester, fatty acid polyglyceride, Fatty acid alcohol polyglycol ether, acetylene glycol, acetylene alcohol, oxyalkylene block polymer, polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene styryl aryl ether, polyoxyethylene glycol alkyl ether, polyethylene glycol, polyoxy Nonionic surfactants such as ethylene fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene glycerin fatty acid ester, polyoxyethylene hydrogenated castor oil, polyoxypropylene fatty acid ester; olive oil, kapok oil, castor oil, palm oil , Coconut oil, palm oil, sesame oil, corn oil, rice bran oil, peanut oil, cottonseed oil, soybean oil, rapeseed oil, linseed oil Tung oil, vegetable oil or mineral oil such as liquid paraffin; and the like. Each component of these adjuvants can be used by appropriately selecting one or two or more types without departing from the object of the present invention. In addition to the above-mentioned auxiliary agents, they can be appropriately selected from those known in the art. For example, various commonly used adjuvants such as extenders, thickeners, anti-settling agents, antifreeze agents, dispersion stabilizers, safeners, and antifungal agents can be used. The compounding ratio of the compound of the present invention and various adjuvants is 0.001: 99.999 to 95: 5, preferably 0.005: 99.995 to 90:10. In actual use of these preparations, use them as they are, or dilute them to a predetermined concentration with a diluent such as water, and add various spreading agents (surfactants, vegetable oils, mineral oils, etc.) as necessary. Can be used.

Application of the agricultural and horticultural pest control agent containing the compound of the present invention cannot be defined unconditionally due to differences in weather conditions, formulation form, application time, application location, type of pests and occurrence, etc., but generally 0.05 to 800,000 ppm The active ingredient concentration is preferably 0.5 to 500,000 ppm, and the application amount per unit area is 0.05 to 50,000 g, preferably 1 to 30,000 g of the compound of the present invention per hectare. In addition, application of the agricultural and horticultural pest control agent, which is another desirable embodiment of the pest control agent containing the compound of the present invention, is performed according to the application of the pest control agent. The present invention also includes a method for controlling pests by such an application method, particularly a method for controlling plant parasitic mites, agricultural pests, and plant parasitic nematodes.

Application of various preparations or dilutions of agricultural and horticultural pesticides containing the compound of the present invention is usually performed by a commonly used application method, that is, spraying (for example, spraying, spraying, misting, atomizing, It can be carried out by powder application, water surface application, etc.), soil application (mixing, irrigation, etc.), surface application (application, powder coating, coating, etc.), immersion poison bait, etc. It is also possible to feed livestock with the above-mentioned active ingredient mixed with feed to inhibit the occurrence and growth of harmful insects, particularly harmful insects, in the excreta. It can also be applied by the so-called ultra-low concentration low volume method. In this method, it is possible to contain 100% of the active ingredient.

In addition, the agricultural and horticultural pest control agent containing the compound of the present invention can be mixed or used in combination with other agricultural chemicals, fertilizers, safeners, etc. There is. Other agrochemicals include herbicides, insecticides, acaricides, nematicides, soil insecticides, fungicides, antiviral agents, attractants, antibiotics, plant hormones, plant growth regulators, etc. It is done. In particular, a mixed pest control composition in which the compound of the present invention and one or more active compound compounds of other agricultural chemicals are used in combination or in combination is preferred in terms of application range, timing of chemical treatment, control activity, etc. It is possible to improve. The compound of the present invention and the other active ingredient compounds of other agricultural chemicals may be prepared separately and mixed at the time of spraying, or both may be used together. The present invention includes such a composition for controlling mixed pests.

The mixing ratio between the compound of the present invention and the active ingredient compound of other agricultural chemicals cannot be defined unconditionally due to differences in weather conditions, formulation form, application time, application location, type of pests and occurrence, etc., but generally from 1: 300 to 300: 1, preferably 1: 100 to 100: 1. The appropriate amount to be applied is 0.1 to 50,000 g, preferably 1 to 30,000 g as the total amount of active ingredient compounds per hectare. The present invention also includes a method for controlling pests by a method for applying such a composition for controlling mixed pests.

In the above-mentioned other agricultural chemicals, as an active ingredient compound of an insecticide, acaricide, nematicide or soil pesticide (generic name; including some pending applications or Japan Plant Protection Association test code), for example Profenofos, dichlorvos, fenamiphos, fenitrothion, EPN, diazinon, chlorpyrifos, chlorpyrifos-methyl, acephate, prothiophos, prothiophos Fosthiazate, cadusafos, dislufoton, isoxathion, isofenphos, ethion, etrimfos, quinalphos, dimethylvinphos, dimethoate ), Sulprofos, thiometon, Vmidothion, pyraclofos, pyridaphenthion, pirimiphos-methyl, propaphos, phosalone, formothion, malathion, tetrachlovinphos, tetrachlovinphos Chlorfenvinphos, cyanophos, trichlorfon, methidathion, phenthoate, ESP, azinphos-methyl, fenthion, heptenophos, methoxychlor ), Parathion, phosphocarb, demeton-S-methyl, monocrotophos, metamidophos, imicyafos, parathion-methyl, Terbufos, ho Famidon (phosphamidon), phosmet (phosmet), organic phosphoric acid ester compounds such as folate (phorate);
Carbaryl, propoxur, aldicarb, carbofuran, thiodicarb, methomyl, oxamyl, ethiofencarb, pirimicarb, fenobucarb, fenobucarb Carbamates such as carbosulfan, benfuracarb, bendiocarb, furathiocab, isoprocarb, metolcarb, xylylcarb, XMC, fenothiocarb Compound;
Nereistoxin derivatives such as cartap, thiocyclam, bensultap, sodium thiosultap-sodium;
Organochlorine compounds such as dicofol, tetradifon, endosulfan, dienochlor, dieldrin;

Organometallic compounds such as fenbutatin oxide and cyhexatin;
Fenvalerate, permethrin, cypermethrin, deltamethrin, cyhalothrin, tefluthrin, etofenprox, flufenprox, cyfluthrin , Fenpropathrin, flucytrinate, fluvalinate, cycloprothrin, lambda-cyhalothrin, pyrethrin, esfenvalerate, Tetramethrin, resmethrin, protrifenbute, bifenthrin, zeta-cypermethrin, acrinathrin, alpha-cypermethri n), allethrin, gamma-cyhalothrin, theta-cypermethrin, tau-fluvalinate, tralomethrin, profluthrin, beta cypermethrin ( pyrethroid compounds such as beta-cypermethrin, beta-cyfluthrin, metofurthrin, phenothrin;
Diflubenzuron, chlorfluazuron, teflubenzuron, flufenoxuron, triflumuron, hexaflumuron, lufenuron, novaluron, novaluron, ), Bistrifluron, benzoylurea compounds such as fluazuron;
Juvenile hormone-like compounds such as metoprene, pyriproxyfen, phenoxycarb, diofenolan;
Pyrazole compounds such as fenpyroximate, fipronil, tebufenpyrad, etiprole, tolfenpyrad, acetoprole, pyrafluprole, pyriprole;
Neonicochioids such as imidacloprid, nitenpyram, acetamiprid, thiacloprid, thiamethoxam, clothianidin, dinotefuran, nithiazine;
Hydrazine compounds such as tebufenozide, methoxyfenozide, chromafenozide, halofenozide;

Pyridine compounds such as pyridalyl, flonicamid and the like;
Tetronic acid compounds such as spirodiclofen;
Strobilurin-based compounds such as fluacrypyrim;
Pyridinamine 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 (1,3-dichloropropene), diafenthiuron, benclothiaz, bifenazate, spiromesifen, spirotetramat, propargi Propargite, clofentezine, metaflumizone, flubendiamide, cyflumetofen, chlorantraniliprole, cyenopyrafen, pyrifluquinazon, pirafluquinazon ), Pyridaben, amidoflumet, chlorobenzoate, sulfluramid, hydramethylnon, metaldehyde, HGW 86, ryanodine, and the like; Can be mentioned. Furthermore, Bacillus thuringienses aizawai, Bacillus thuringienses kurstaki, Bacillus thuringienses israelensis, Bacillus thuringienses japonensis, Bacillus thuringienses tenebrionis, crystalline protein toxins produced by Bacillus thuringienses, entomopathogenic fungi, nematode pathogenic fungi, etc. Microbial pesticides such as: avermectin, emamectin-benzoate, milbemectin, milbemycin, spinosad, ivermectin, lepimectin, DE-175, abamectin and antibiotics such as abamectin and emamectin; semi-synthetic antibiotics; natural products such as azadirachtin and rotenone; repellents such as deet;

Examples of the bactericidal active ingredient compounds (generic name; including partial application or Japanese Plant Protection Association test code) in the above-mentioned other agricultural chemicals include, for example, mepanipyrim, pyrimethanil, cyprodinil Anilinopyrimidine compounds such as ferimzone;
Tria such as 5-chloro-6- (2,4,6-trifluorophenyl) -7- (4-methylpiperidin-1-yl) [1,2,4] triazolo [1,5-a] pyrimidine Zolopyrimidine compounds;
Pyridinamine compounds such as fluazinam;
Triadimefon, bitertanol, triflumizole, etaconazole, propiconazole, penconazole, flusilazole, microbutanil, cyproconazole cyproconazole), tebuconazole, hexaconazole, furconazole-cis, prochloraz, metconazole, epoxiconazole, tetraconazole, o Oxpoconazole fumarate, sipconazole, prothioconazole, triadimenol, flutriafol, difenoconazole , Fluquinconazole, fenbuconazole, bromuconazole, diniconazole, tricyclazole, probenazole, cimeconazole, pefurazoate, ipconazole, ipconazole ), Azole compounds such as imibenconazole;

Quinoxaline compounds such as quinomethionate;
Dithiocarbamate compounds such as maneb, zineb, mancozeb, polycarbamate, metiram, propineb, thiram;
Organochlorine compounds such as fthalide, chlorothalonil, quintozene;
Imidazole compounds such as benomyl, thiophanate-methyl, carbendazim, thiabendazole, fuberiazole, cyazofamid;
Cyanoacetamide compounds such as cymoxanil;
Metalaxyl, metalaxyl-M, mefenoxam, oxadixyl, offurace, benalaxyl, benalaxyl-M, also known as kiralaxyl, chiax ), Phenylamide compounds such as furalaxyl, cyprofuram;

Sulfenic acid compounds such as dichlofluanid;
Copper-based compounds such as cupric hydroxide and oxine copper;
Isoxazole compounds such as hymexazol;
Fosetyl aluminum (fosetyl-Al), tolclofos-methyl, edifenphos, iprobenfos, S-benzyl O, O-diisopropyl phosphorothioate, O-ethyl S, S-diphenyl phosphorodithioate, aluminum Organophosphorus compounds such as ethyl hydrogen phosphonate;
N-halogenothioalkyl compounds such as captan, captafol, folpet;
Dicarboximide compounds such as procymidone, iprodione, vinclozolin;

Benzanilide compounds such as flutolanil, mepronil, zoxamid, tiadinil;
Carboxin (carboxin), oxycarboxin, thifluzamide, penthiopyrad, boscalid, isothianil, bixafen, 3- (difluoromethyl) -1-methyl-N- [(1RS, 4SR, 9RS) -1,2,3,4-Tetrahydro-9-isopropyl-1,4-methanonaphthalen-5-yl] pyrazole-4-carboxamide and 3- (difluoromethyl) -1-methyl- Of a mixture of N-[(1RS, 4SR, 9SR) -1,2,3,4-tetrahydro-9-isopropyl-1,4-methanonaphthalen-5-yl] pyrazole-4-carboxamide (isopyrazam) Such anilide compounds;
Piperazine compounds such as triforine;
Pyridine compounds such as pyrifenox;
Carbinol compounds such as fenarimol, flutriafol;
Piperidine-based compounds such as fenpropidine;
Morpholine compounds such as fenpropimorph, spiroxamine, tridemorph;

Organotin compounds such as fentin hydroxide and fentin acetate;
Urea-based compounds such as pencycuron;
Synamic acid compounds such as dimethomorph and flumorph;
Phenyl carbamate compounds such as dietofencarb;
Cyanopyrrole compounds such as fludioxonil and fenpiclonil;
Azoxystrobin, kresoxim-methyl, metominofen, trifloxystrobin, picoxystrobin, oryzastrobin, dimoxystrobin Strobilurin-based compounds such as pyraclostrobin, fluoxastrobin, fluacrypyrin;

Oxazolidinone compounds such as famoxadone;
Thiazole carboxamide compounds such as ethaboxam;
Silylamide compounds such as silthiopham;
Iprovalicarb, Benthiavalicarb-isopropyl, methyl [S- (R, S)]-[3- (N-isopropoxycarbonylvalinyl) -amino] -3- (4-chloro Aminoacid amide carbamate compounds such as -phenyl) propionate (valiphenal);
Imidazolidine compounds such as fenamidone;
Hydroxyanilide 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, polyoxins;
Guanidine compounds such as iminoctadine and dodine;
4-quinolinol derivative compounds such as 6-tertiarybutyl-8-fluoro-2,3-dimethylquinolin-4-yl acetate;
Cyanomethylene compounds such as 2- (2-fluoro-5- (trifluoromethyl) phenylthio) -2- (3- (2-methoxyphenyl) thiazolidine-2-ylidene) acetonitrile;

As other compounds, isoprothiolane, pyroquilon, diclomezine, quinoxyfen, propamocarb hydrochloride, chloropicrin, dazomet, metam sodium salt ( metam-sodium, nicobifen, metrafenone, MTF-753, UBF-307, diclocymet, proquinazid, amisulbrom, pyribencarb, mandipropamid, flupropamide fluopicolide spp., carpropamid, meptyldinocap, fluopyram, BCF051, BCM061, BCM062; and the like.

Other pesticides that can be used in combination with or combined with the compounds of the present invention include, for example, active ingredient compounds of herbicides such as those described in The な ど Pesticide Manual (14th edition), especially those of soil treatment type. is there.

Examples of animal parasite control agents include ectoparasites that parasitize on the body surface of the host animal (back, armpit, lower abdomen, inner thigh, etc.) and the host animal body (stomach, intestinal tract, lung, heart, liver). , Vascular, subcutaneous, lymphoid tissue, etc.) are effective in controlling endoparasites, and in particular, are effective in controlling ectoparasites.

Examples of ectoparasites include animal parasitic mites and fleas. There are so many of these types that it is difficult to list them all.

The animal parasitic mites, for example Boophilus microplus (Boophilus microplus), Rhipicephalus sanguineus (Rhipicephalus sanguineus), Haemaphysalis longicornis (Haemaphysalis longicornis), Haemaphysalis flava (Haemaphysalis flava), Adenophora chima tick (Haemaphysalis campanulata), Isukachimadani (Haemaphysalis concinna), Yamatochimadani (Haemaphysalis japonica), H. kitaokai (Haemaphysalis kitaokai), Iyasuchimadani (Haemaphysalis ias), Ixodes ovatus (Ixodes ovatus), I. nipponensis (Ixodes nipponensis), Schulze ticks (Ixodes persulcatus), Takasago testudinarium (Amblyomma testudinarium), Ootogechimadani (Haemaphysalis megaspinosa ), tick such as Dermacentor reticulatus , Dermacentor taiwanesis ; duck ( Dermanyssus gallinae ); Shidani (Ornithonyssus sylviarum), Torisashidani, such as Southern tri sand mite (Ornithonyssus bursa); Nan iodine tsutsugamushi (Eutrombicula wichmanni), red mites (Leptotrombidium akamushi), L. pallidum (Leptotrombidium pallidum), Fuji chiggers (Leptotrombidium fuji), Tosa mites ( Leptotrombidium tosa), Europe Aki mites (Neotrombicula autumnalis), the United States chiggers (Eutrombicula alfreddugesi), chiggers, such as Miyagawa Tama chiggers (Helenicula miyagawai); Inutsumedani (Cheyletiella yasguri), rabbit Tsumedani (Cheyletiella parasitivorax), Nekotsumedani (Cheyletiella blakei) Tsumedani, such as; rabbits 9,000 mite (Psoroptes cuniculi), Ushishokuhidani (Chorioptes bovis), dog ear mites (Otodectes cynotis), mange mites (Sar coptes scabiei ), mite mites like Notoedres cati ; mite mites like Demodex canis , and the like. Among them, the animal parasite control agent containing the compound of the present invention is particularly effective for controlling ticks and the like.

Examples of fleas include ectoparasite worms belonging to the order Flea ( Siphonaptera ), and more specifically fleas belonging to the family Flea family ( Pulicidae ), Nagano family ( Ceratephyllus ) and the like. Examples of fleas belonging to the family flea family include, for example, dog fleas ( Ctenocephalides canis ), cat fleas ( Ctenocephalides felis ), human fleas ( Purex irritans ), elephant fleas ( Echidnophaga gallinacea ), keops mouse fleas ( Xenopsylla cheopis ) Leptopsylla segnis ), European mud minnow ( Nosopsyllus fasciatus ), and Yamato mud mink ( Monopsyllus anisus ). Among them, the animal parasite control agent containing the compound of the present invention is effective for controlling fleas belonging to the family Flea, particularly dog fleas, cat fleas and the like.

Other ectoparasites include, for example, lice such as bovine lice, foal lice, sheep lice, bovine white lice, head lice; lice such as dog lice; blood-sucking dipterous pests such as bovine abs, quail sharks, . In addition, examples of endoparasites include nematodes such as lungworms, benthic worms, tuberous worms, gastric parasites, roundworms, and filamentous worms; Tapeworms such as real tapeworms, multi-headed tapeworms, single-banded tapeworms, multi-banded tapeworms; Japanese schistosomiasis, fluke like liver fluke; coccidium, malaria parasite, intestinal granulocyst, toxoplasma, chestnut Protozoa such as Ptosporidium, and the like.

Examples of host animals include various pet animals, livestock, poultry, etc., and more specifically dogs, cats, mice, rats, hamsters, guinea pigs, squirrels, rabbits, ferrets, birds (eg, pigeons, parrots, (E.g., nine-bird, bird, parakeet, juvenile pine, canary, etc.), cattle, horses, pigs, sheep, ducks, chickens, etc. Among them, the animal parasite control agent containing the compound of the present invention is effective for controlling pests parasitic on pet animals or livestock, particularly ectoparasites. Among pet animals or domestic animals, it is particularly effective for dogs, cats, cows or horses.

When the compound of the present invention is used as an animal parasite control agent, it may be used as it is. In addition, it can be used in the form of various forms such as powders, granules, tablets, powders, capsules, liquids, emulsions, aqueous suspensions, oily suspensions and the like together with appropriate auxiliary agents. In addition to the above-mentioned preparation forms, any preparation forms used in the normal field can be used as long as the object of the present invention is met. Examples of the adjuvant used in the preparation include anionic surfactants and nonionic surfactants exemplified as the above-mentioned preparation adjuvants for agricultural and horticultural pest control agents; positive agents such as cetyltrimethylammonium bromide. Ionic surfactants: water, acetone, acetonitrile, N-methylacetamide, N, N-dimethylacetamide, N, N-dimethylformamide, 2-pyrrolidone, N-methyl-2-pyrrolidone, kerosene, triacetin, methanol, Ethanol, isopropanol, benzyl alcohol, ethylene glycol, propylene glycol, polyethylene glycol, liquid polyoxyethylene glycol, butyl diglycol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monoethyl Solvents such as ether, diethylene glycol normal butyl ether, dipropylene glycol monomethyl ether, dipropylene glycol normal butyl ether; oxidations such as butylhydroxyanisole, butylhydroxytoluene, ascorbic acid, sodium metabisulfite, propyl gallate, sodium thiosulfate Inhibitors; Film forming agents such as polyvinylpyrrolidone, polyvinyl alcohol, vinyl acetate and vinylpyrrolidone copolymers; vegetable oils and mineral oils exemplified as preparations for the aforementioned agricultural and horticultural pest control agents; lactose, sucrose, glucose , Starch, wheat flour, corn flour, soybean oil cake, defatted rice bran, calcium carbonate, and other carriers such as commercially available feed materials. Each component of these adjuvants can be used by appropriately selecting one or two or more types without departing from the object of the present invention. In addition to the above-mentioned adjuvants, it can be used by appropriately selecting from those known in the field, and further, selected from various adjuvants used in the above-mentioned agricultural and horticultural fields. You can also

The compounding ratio of the compound of the present invention and various adjuvants is usually about 0.1: 99.9 to 90:10. In actual use of these preparations, use them as they are, or dilute them to a predetermined concentration with a diluent such as water, and add various spreading agents (surfactants, vegetable oils, mineral oils, etc.) as necessary. Can be used.

Administration of the compound of the present invention to the host animal is performed orally or parenterally. Examples of the oral administration method include a method of administering tablets, liquid agents, capsules, wafers, biscuits, minced meat, and other feeds containing the compound of the present invention. As a parenteral administration method, for example, the compound of the present invention is prepared into an appropriate preparation and then taken into the body by intravenous administration, intramuscular administration, intradermal administration, subcutaneous administration, etc .; spot-on For example, a method of administering to the body surface by treatment, pour-on treatment, spray treatment, etc .; a method of embedding a resin piece containing the compound of the present invention under the skin of a host animal, and the like.

The dose of the compound of the present invention to the host animal varies depending on the administration method, administration purpose, disease symptoms, etc., but is usually a ratio of 0.01 mg to 100 g, preferably 0.1 mg to 10 g, per 1 kg body weight of the host animal. Is suitable for administration.

The present invention includes a method for controlling pests according to the administration method or dosage as described above, particularly a method for controlling ectoparasites or endoparasites.

Further, in the present invention, there are cases where various diseases of host animals caused by them can be prevented or treated by controlling animal parasitic pests as described above. As described above, the present invention includes a prophylactic or therapeutic agent for parasitic animal diseases containing the compound of the present invention as an active ingredient, and a method for preventing or treating parasitic animal diseases.

When the compound of the present invention is used as an animal parasite control agent, various vitamins, minerals, amino acids, nutrients, enzyme preparations, antipyretics, sedatives, anti-inflammatory agents, bactericides, coloring agents, fragrances, together with adjuvants These can be used in combination with or in combination with preservatives. Also, if necessary, mix or use with other animal drugs and pesticides such as anthelmintics, anticoccidials, insecticides, acaricides, fleas, nematicides, fungicides, antibacterials, etc. In this case, a more excellent effect may be exhibited. The present invention includes a composition for controlling mixed pests in which various components as described above are mixed or used together, and a method for controlling pests using the composition, particularly a method for controlling ectoparasites or endoparasites. Is also included.

Next, although an example of the desirable mode of the present invention is described, the present invention is not limited to these.
(1) In formula (I), R ¹ is alkyl optionally substituted with A, cycloalkyl optionally substituted with A, alkenyl optionally substituted with A, alkynyl optionally substituted with A, halogen atoms, cyano, aryl which may be substituted by an alkyl heterocyclic ^{group, CH = NOR 2, CH =} NNR 4 R 5, COR 2, COOR 2, OR 2, S (O) n R 3, NR 4 R 5 Or CONR ⁴ R ⁵ ; X is alkyl, alkenyl, alkynyl, aryl, halogen atom, haloalkyl, cyano, nitro, NR ⁴ R ⁵ , S (O) _n R ³ , OR ² , COR ² or COOR ² A is a halogen atom, OR ² , S (O) _n R ³ , OS (O) _n R ³ , NR ⁴ R ⁵ , cyano, alkyl, cycloalkyl, aryl, heterocyclic group, SCH ₂ COOR ² , NHNR ⁴ R ⁵ , COOR ² , nitro Or —CH (CN) ₂ ; R ² is a hydrogen atom, alkyl, alkenyl, alkynyl, haloalkyl, cyanoalkyl, alkoxyalkyl, acetyl or aryl; R ³ is alkyl or acetyl; R ⁴ is a hydrogen atom Or R ⁵ is a hydrogen atom, alkyl, haloalkyl, COR ² , COOR ² , CH ₂ CH ₂ OR ² or CH ₂ CN; m is an integer of 1 to 4; n is 0 to 2 An integer pyridyl-triazolopyrimidine derivative or a salt thereof.
(2) R ¹ is alkyl optionally substituted with A, cycloalkyl optionally substituted with A, alkenyl optionally substituted with A, alkynyl optionally substituted with A, halogen atom, substituted with alkyl An optionally heterocyclic group, CH═NOR ² , CH═NNR ⁴ R ⁵ , COR ² , COOR ² , OR ² , S (O) _n R ³ , NR ⁴ R ⁵ or CONR ⁴ R ⁵ ; Alkyl, aryl, halogen atom, haloalkyl or OR ² ; A is a halogen atom, OR ² , S (O) _n R ³ , OS (O) _n R ³ , NR ⁴ R ⁵ , alkyl, cycloalkyl, heterocycle A group, NHNR ⁴ R ⁵ , COOR ² or nitro; R ² is a hydrogen atom, alkyl, haloalkyl or cyanoalkyl; R ³ is alkyl; R ⁵ is a hydrogen atom, alkyl, haloalkyl, COR ² or COOR ² Triazolopyrimidine derivative or a salt thereof - pyridyl according to (1).
(3) R ¹ is may be substituted by A alkyl, cycloalkyl which may be substituted by A, it may be substituted by A ^{alkenyl, CH = NOR 2, CH =} NNR 4 R 5, COR 2, COOR ² , NR ⁴ R ⁵ or CONR ⁴ R ⁵ ; pyridyl according to (2), wherein A is OR ² , S (O) _n R ³ , OS (O) _n R ³ , NR ⁴ R ⁵ or nitro. A triazolopyrimidine derivative or a salt thereof.
(4) R ¹ is may be substituted by A alkyl, cycloalkyl which may be substituted by A, it may be substituted by A ^{alkenyl, CH = NOR 2, CH =} NNR 4 R 5, COR 2, COOR ² , NR ⁴ R ⁵ or CONR ⁴ R ⁵ ; A is OR ² , S (O) _n R ³ , OS (O) _n R ³ , NR ⁴ R ⁵ or nitro; R ⁵ is haloalkyl, COR The pyridyl-triazolopyrimidine derivative or a salt thereof according to (2), which is ² or COOR ² .
(5) The pyridyl-triazolopyrimidine derivative or a salt thereof according to (1), wherein X is OR ² .
(6) The pyridyl-triazolopyrimidine derivative or a salt thereof according to (2), wherein R ¹ is NR ⁴ R ⁵ ; R ⁵ is a hydrogen atom, alkyl, haloalkyl, COR ² or COOR ² .

(7) The pyridyl-triazolopyrimidine derivative or a salt thereof according to (6), wherein R ⁵ is haloalkyl, COR ² or COOR ² .
(8) The pyridyl-triazolopyrimidine derivative or a salt thereof according to (6), wherein R ⁵ is a hydrogen atom or COR ² .
(9) A pest control agent comprising the pyridyl-triazolopyrimidine derivative or a salt thereof according to (1) as an active ingredient.
(10) An agricultural and horticultural pest control agent comprising the pyridyl-triazolopyrimidine derivative or a salt thereof according to (1) as an active ingredient.
(11) An insecticide, acaricide, nematicide or soil insecticide containing the pyridyl-triazolopyrimidine derivative or a salt thereof according to (1) as an active ingredient.
(12) An insecticide or acaricide containing the pyridyl-triazolopyrimidine derivative or a salt thereof according to (1) as an active ingredient.
(13) A method for controlling pests by applying an effective amount of the pyridyl-triazolopyrimidine derivative or a salt thereof according to (1).

Next, examples of the present invention will be described, but the present invention should not be construed as being limited thereto. First, the synthesis example of this invention compound is described.

Synthesis example 1
Synthesis of 7- [3-chloro-5- (trifluoromethyl) pyridin-2-yl] -5-formyl [1,2,4] triazolo [1,5-a] pyrimidine (Compound No. 18)
(1) 2-acetyl-3-chloro-5- (trifluoromethyl) pyridine (1.0 g) and N, N-dimethylacetamide dimethylacetal (715 mg) were reacted in toluene (6 ml) at 100 ° C. for 14 hours. The reaction mixture was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (eluent: ethyl acetate) to give 1- [3-chloro-5- (trifluoromethyl) pyridine- 869 mg of 2-yl] -3- (dimethylamino) -2-buten-1-one was obtained.
(2) 1- [3-Chloro-5- (trifluoromethyl) pyridin-2-yl] -3- (dimethylamino) -2-buten-1-one 850 mg was dissolved in 3 ml of acetic acid, and 3-amino- 244 mg of 1H-1,2,4-triazole was added and heated to reflux for 17 hours. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate solution and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: n-hexane / ethyl acetate = 1/1), and 7- [3-chloro-5- (trifluoromethyl) pyridin-2-yl having a melting point of 105-107 ° C. 609 mg of] -5-methyl [1,2,4] triazolo [1,5-a] pyrimidine was obtained.
(3) 8.0 g of 7- [3-chloro-5- (trifluoromethyl) pyridin-2-yl] -5-methyl [1,2,4] triazolo [1,5-a] pyrimidine and N, N -A mixed solution of 25 ml of dimethylformamide dimethylacetal was heated to reflux for 12 hours. After completion of the reaction, the reaction solution was concentrated under reduced pressure. To a mixed solution of the obtained residue and 30 ml of N, N-dimethylformamide, a mixed solution of 17.1 g of sodium periodate and 60 ml of water was slowly added dropwise and stirred at room temperature for 5 hours. Insoluble solids were removed with a pad of celite, followed by extraction twice with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel chromatography (eluent: n-hexane / ethyl acetate = 1/1) to obtain 5.9 g of the desired product as pale yellow crystals.

Synthesis example 2
(E) -7- [3-Chloro-5- (trifluoromethyl) pyridin-2-yl] [1,2,4] triazolo [1,5-a] pyrimidine-5-carbaldehyde O-methyloxime ( Synthesis of Compound No. 1) 7- [3-Chloro-5- (trifluoromethyl) pyridin-2-yl] -5-formyl [1,2,4] triazolo [1,5-a] pyrimidine 33 mg and methanol To 3 ml of the mixed solution, 17 mg of O-methylhydroxylamine hydrochloride and 17 mg of sodium acetate were added and stirred at room temperature for 2 hours. After completion of the reaction, 5 ml of water was added and the mixture was extracted twice with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel chromatography (eluent: n-hexane / ethyl acetate = 2/1) to obtain 27 mg of the desired product as white crystals.

Synthesis example 3
Synthesis of 7- [3-chloro-5- (trifluoromethyl) pyridin-2-yl] -5-dimethoxymethyl [1,2,4] triazolo [1,5-a] pyrimidine (Compound No. 7) 7 -[3-Chloro-5- (trifluoromethyl) pyridin-2-yl] -5-formyl [1,2,4] triazolo [1,5-a] pyrimidine in a mixed solution of 220 mg and methanol Paratoluenesulfonic acid was added and heated to reflux for 7 hours. After completion of the reaction, the mixture was neutralized by adding a saturated aqueous sodium hydrogen carbonate solution, extracted twice with ethyl acetate, the organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel chromatography (eluent: n-hexane / ethyl acetate = 1/1) to obtain 89 mg of the desired product as a colorless oil.

Synthesis example 4
Synthesis of 7- [3-chloro-5- (trifluoromethyl) pyridin-2-yl] -5-hydroxymethyl [1,2,4] triazolo [1,5-a] pyrimidine (Compound No. 36) 7 A mixed solution of 710 mg of [3-chloro-5- (trifluoromethyl) pyridin-2-yl] -5-formyl [1,2,4] triazolo [1,5-a] pyrimidine and 10 ml of methanol was ice-cooled. 164 mg of sodium borohydride was added and stirred for 30 minutes. After completion of the reaction, 5 ml of a saturated aqueous ammonium chloride solution was added, and the mixture was extracted twice with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel chromatography (eluent: n-hexane / ethyl acetate = 1/3) to obtain 336 mg of the desired product as white crystals.

Synthesis example 5
7- [3-Chloro-5- (trifluoromethyl) pyridin-2-yl] -5-methanesulfonyloxymethyl [1,2,4] triazolo [1,5-a] pyrimidine (Compound No. 51) Synthesis 7- [3-Chloro-5- (trifluoromethyl) pyridin-2-yl] -5-hydroxymethyl [1,2,4] triazolo [1,5-a] pyrimidine 136 mg, triethylamine 0.23 ml and chloroform 5 ml of the mixed solution was ice-cooled, 0.05 ml of methanesulfonyl chloride was added, and the mixture was stirred for 1 hour under ice-cooling. After completion of the reaction, 5 ml of water was added and the mixture was extracted twice with chloroform. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel chromatography (eluent: n-hexane / ethyl acetate = 1/1) to obtain 80 mg of the desired product as white amorphous.

Synthesis Example 6
7- [3-Chloro-5- (trifluoromethyl) pyridin-2-yl] -5- (2-methoxyvinyl) [1,2,4] triazolo [1,5-a] pyrimidine (Compound No. 28 ) A suspension of 293 mg of (methoxymethyl) triphenylphosphonium chloride and 8 ml of tetrahydrofuran was ice-cooled, 0.48 ml of a hexane solution (1.6 M) of n-butyllithium was added dropwise, and the mixture was stirred for 30 minutes. To this mixed solution was mixed 140 mg of 7- [3-chloro-5- (trifluoromethyl) pyridin-2-yl] -5-formyl [1,2,4] triazolo [1,5-a] pyrimidine and 1 ml of tetrahydrofuran. The solution was added dropwise and stirred at room temperature overnight. After completion of the reaction, 5 ml of a saturated aqueous ammonium chloride solution was added, and the mixture was extracted twice with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel chromatography (eluent: n-hexane / ethyl acetate = 2/1) to obtain 14 mg of the desired product as white crystals.

Synthesis example 7
7- [3-Chloro-5- (trifluoromethyl) pyridin-2-yl] -5- (oxiran-2-yl) [1,2,4] triazolo [1,5-a] pyrimidine (Compound No. 1) 21) Synthesis 7- [3-Chloro-5- (trifluoromethyl) pyridin-2-yl] -5-formyl [1,2,4] triazolo [1,5-a] pyrimidine 200 mg, trimethyl sulfoiodide 110 mg of potassium tert-butoxide was added to a mixed solution of 215 mg of xsonium and 5 ml of dimethyl sulfoxide, and stirred at room temperature for 20 hours. After completion of the reaction, 10 ml of water was added, followed by extraction twice with ethyl acetate, the organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel chromatography (eluent: n-hexane / ethyl acetate = 1/1) to obtain 34 mg of the desired product as white crystals.

Synthesis example 8
Synthesis of 7- [3-chloro-5- (trifluoromethyl) pyridin-2-yl] [1,2,4] triazolo [1,5-a] pyrimidine-5-carboxylic acid (Compound No. 48) 7 A mixed solution of 1.0 g of 10- [3-chloro-5- (trifluoromethyl) pyridin-2-yl] -5-formyl [1,2,4] triazolo [1,5-a] pyrimidine and 10 ml of acetone was added to ice. After cooling, 3 ml of Jones reagent was slowly added dropwise, and the mixture was stirred for 1 hour under ice cooling. After completion of the reaction, 3 ml of isopropanol was added and stirred at room temperature for 30 minutes. After removing insoluble solids with a pad of celite, 10 ml of water was added and extracted twice with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 394 mg of the desired product as a light brown solid.

Synthesis Example 9
Synthesis of 7- [3-chloro-5- (trifluoromethyl) pyridin-2-yl] -5-methoxycarbonyl [1,2,4] triazolo [1,5-a] pyrimidine (Compound No. 8) 7 Trimethylsilyl in a mixed solution of 50 mg of [3-chloro-5- (trifluoromethyl) pyridin-2-yl] [1,2,4] triazolo [1,5-a] pyrimidine-5-carboxylic acid and 5 ml of diethyl ether 1 ml of a diethyl ether solution of diazomethane (2M) was added and stirred at room temperature for 1 hour. After completion of the reaction, excess trimethylsilyldiazomethane was decomposed with 1 ml of acetic acid. Next, the mixture was neutralized by adding a saturated aqueous sodium hydrogen carbonate solution, and extracted twice with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel chromatography (eluent: n-hexane / ethyl acetate = 2/1) to obtain 33 mg of the desired product as white crystals.

Synthesis Example 10
tert-Butyl 7- [3-chloro-5- (trifluoromethyl) pyridin-2-yl] [1,2,4] triazolo [1,5-a] pyrimidin-5-ylcarbamate (Compound No. 23) Synthesis of 7- [3-Chloro-5- (trifluoromethyl) pyridin-2-yl] [1,2,4] triazolo [1,5-a] pyrimidine-5-carboxylic acid 394 mg, tert-butanol To a mixed solution of 34 ml and 10 ml of toluene, 0.28 ml of diphenylphosphoric acid azide and then 0.18 ml of triethylamine were added and heated to reflux for 3 hours. After completion of the reaction, 10 ml of water was added and the mixture was extracted twice with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel chromatography (eluent: n-hexane / ethyl acetate = 1/1) to obtain 178 mg of the desired product as white crystals.

Synthesis Example 11
Synthesis of 5-amino-7- [3-chloro-5- (trifluoromethyl) pyridin-2-yl] [1,2,4] triazolo [1,5-a] pyrimidine (Compound No. 15) tert- In a mixed solution of 178 mg of butyl 7- [3-chloro-5- (trifluoromethyl) pyridin-2-yl] [1,2,4] triazolo [1,5-a] pyrimidin-5-ylcarbamate and 10 ml of chloroform 1 ml of trifluoroacetic acid was added and heated to reflux for 12 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel chromatography (eluent: ethyl acetate / methanol = 15/1) to obtain 147 mg of the desired product as white crystals.

Synthesis Example 12
N- {7- [3-Chloro-5- (trifluoromethyl) pyridin-2-yl] [1,2,4] triazolo [1,5-a] pyrimidin-5-yl} -2,2,2 Of 2-trifluoroacetamide (Compound No. 26) 5-Amino-7- [3-chloro-5- (trifluoromethyl) pyridin-2-yl] [1,2,4] triazolo [1,5-a ] To a mixed solution of 56 mg of pyrimidine, a catalytic amount of 4-dimethylaminopyridine and 1 ml of pyridine, 0.5 ml of trifluoroacetic anhydride was added dropwise and stirred at room temperature for 12 hours. After completion of the reaction, the reaction solution was concentrated under reduced pressure, and the resulting residue was purified by silica gel chromatography (eluent: n-hexane / ethyl acetate = 1/1) to obtain 15 mg of the desired product as white crystals. .

Synthesis Example 13
7- [3-Chloro-5- (trifluoromethyl) pyridin-2-yl] -5-iodo [1,2,4] triazolo [1,5-a] pyrimidine (Compound No. 40) and 7- [ Synthesis of 3-chloro-5- (trifluoromethyl) pyridin-2-yl] -5-hydroxy [1,2,4] triazolo [1,5-a] pyrimidine (Compound No. 41) 5-amino-7 A mixed solution of 61 mg of [3-chloro-5- (trifluoromethyl) pyridin-2-yl] [1,2,4] triazolo [1,5-a] pyrimidine, 148 mg of iodine and 5 ml of acetonitrile was ice-cooled, 0.05 ml of tert-butyl nitrite was added. The reaction mixture was stirred for 30 minutes under ice cooling and then overnight at room temperature. After completion of the reaction, 5 ml of water was added and the mixture was extracted twice with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel chromatography (eluent: n-hexane / ethyl acetate = 1/1) to obtain 12 mg of the desired product (Compound No. 40) and the desired product (Compound). No. 41) 16 mg was obtained as white crystals.

Synthesis Example 14
7- [3-Chloro-5- (trifluoromethyl) pyridin-2-yl] -5- (1-ethoxyethyl) [1,2,4] triazolo [1,5-a] pyrimidine (Compound No. 12 ) Synthesis
(1) To a mixed solution of 6.0 g of ethyl 3-chloro-5- (trifluoromethyl) pyridine-2-carboxylate, 2.6 g of methyl ethyl ketone and 80 ml of tetrahydrofuran (dehydrated) was added 3.2 g of sodium ethoxide at room temperature. Stir for minutes. After completion of the reaction, the reaction mixture was acidified with 1N hydrochloric acid, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to give 1- [3-chloro- The presence of 5- (trifluoromethyl) pyridin-2-yl] -pentane-1,3-dione was confirmed by ¹ H-NMR. Its ¹ H-NMR δppm (Solvent: CDCl ₃ / 400MHz) is 1.22 (3H, t, J = 7.2Hz), 2.48 (2H, q, J = 7.2Hz), 6.28 (1H, s), 8.02 (1H , s), 8.77 (1H, s).
(2) To the total amount of liquid containing 1- [3-chloro-5- (trifluoromethyl) pyridin-2-yl] -pentane-1,3-dione obtained in (1), 65 ml of acetic acid and 3- Amino-1H-1,2,4-triazole (2.2 g) was added, and the mixture was stirred at 100 ° C. overnight. After completion of the reaction, the solvent was distilled off under reduced pressure, water was added to the resulting residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and then dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: n-hexane / ethyl acetate = 3/1), and 7- [3-chloro-5- (trifluoromethyl) pyridin-2-yl] -5-ethyl [ 3.1 g of 1,2,4] triazolo [1,5-a] pyrimidine was obtained. Its ¹ H-NMR δppm (Solvent: CDCl ₃ / 400MHz) is 1.47 (3H, t, J = 8.0Hz), 3.09 (2H, q, J = 8.0Hz), 7.17 (1H, s), 8.21 (1H , d, J = 1.6Hz), 8.47 (1H, s), 8.98 (1H, m).

(3) 7- [3-Chloro-5- (trifluoromethyl) pyridin-2-yl] -5-ethyl [1,2,4] triazolo [1,5-a] pyrimidine (5.76 g) in 30 ml of chloroform To the dissolved solution, 4.47 g of N-bromosuccinimide and 50 mg of azobisisobutyronitrile (AIBN) were added, and the mixture was stirred overnight with heating under reflux. After completion of the reaction, water was added to the reaction solution, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: n-hexane / ethyl acetate = 5/2) to give 5- (1-bromoethyl) -7- [3-chloro-5- (trifluoromethyl) pyridine-2. There was obtained 4.47 g of -yl] [1,2,4] triazolo [1,5-a] pyrimidine as a solid with a melting point of 118 ° C.

(4) 840 mg of 5- (1-bromoethyl) -7- [3-chloro-5- (trifluoromethyl) pyridin-2-yl] [1,2,4] triazolo [1,5-a] pyrimidine and dimethyl 30 mg of silver tetrafluoroborate was added to a mixed solution of 10 ml of sulfoxide and stirred overnight at room temperature. After completion of the reaction, 10 ml of water was added and the mixture was extracted twice with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. By distilling off the solvent under reduced pressure, 7- [3-chloro-5- (trifluoromethyl) pyridin-2-yl] -5- (1-hydroxyethyl) [1,2,4] triazolo [1 , 5-a] pyrimidine was obtained as white crystals with a melting point of 178 ° C.

(5) 7- [3-chloro-5- (trifluoromethyl) pyridin-2-yl] -5- (1-hydroxyethyl) [1,2,4] triazolo [1,5-a] pyrimidine 100 mg, A mixed solution of 0.2 ml of 10N aqueous sodium hydroxide and 5 ml of N, N-dimethylformamide was ice-cooled, and 0.2 ml of ethyl iodide was added. The reaction solution was stirred under ice-cooling for 30 minutes and then at room temperature for 4 hours. After completion of the reaction, 5 ml of a saturated aqueous ammonium chloride solution was added, and the mixture was extracted twice with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel chromatography (eluent: n-hexane / ethyl acetate = 1/1) to obtain 63 mg of the desired product as colorless crystals.

Synthesis Example 15
Synthesis of 5-acetyl-7- [3-chloro-5- (trifluoromethyl) pyridin-2-yl] [1,2,4] triazolo [1,5-a] pyrimidine (Compound No. 3) 7- [3-Chloro-5- (trifluoromethyl) pyridin-2-yl] -5- (1-hydroxyethyl) [1,2,4] triazolo [1,5-a] pyrimidine 240 mg and acetone 5 ml mixed solution The mixture was ice-cooled, and 1 ml of Jones reagent was slowly added dropwise, followed by stirring under ice-cooling for 30 minutes and then at room temperature for 1 hour. After completion of the reaction, 1 ml of isopropanol was added and stirred at room temperature for 30 minutes. After removing insoluble solids with a pad of celite, 5 ml of water was added and extracted twice with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel chromatography (eluent: n-hexane / ethyl acetate = 2/1) to obtain 152 mg of the desired product as white crystals.

Synthesis Example 16
Synthesis of 5-cyclopropyl-7- [3-iodo-5- (trifluoromethyl) pyridin-2-yl] [1,2,4] triazolo [1,5-a] pyrimidine (Compound No. 74)
(1) After adding 72 g of potassium fluoride in 400 ml of dimethyl sulfoxide and stirring at 120 ° C. for 10 minutes, 127 g of 2-chloro-3-iodo-5- (trifluoromethyl) pyridine was added and stirred at 120 ° C. for 2 hours. . After completion of the reaction, the reaction solution was returned to room temperature, and the precipitated solid was filtered to obtain a filtrate containing 2-fluoro-3-iodo-5- (trifluoromethyl) pyridine. To the total amount of the filtrate obtained, 22.3 g of sodium cyanide and 6.7 g of tetrabutylammonium bromide were added and stirred at 50 ° C. for 6 hours. After completion of the reaction, the reaction solution was poured into 4,000 ml of water, and the precipitated solid was filtered. The obtained solid was purified by silica gel column chromatography (eluent: n-hexane / ethyl acetate = 95/5) to obtain 87 g of 3-iodo-5- (trifluoromethyl) pyridine-2-carbonitrile as white crystals. Got as. Its ^{1 H-NMR δppm (Solvent:} CDCl 3 / 400MHz) is, 8.44 (1H, s), was 8.90 (1H, s).
(2) After slowly adding 520 ml of 96% sulfuric acid to 60 ml of water, 87 g of 3-iodo-5- (trifluoromethyl) pyridine-2-carbonitrile was added at room temperature, and the mixture was stirred at 120 ° C. for 3 hours. . After completion of the reaction, the reaction solution was poured into 5,000 ml of ice water, and the resulting crystals were filtered, washed with water, and dried to give 3-iodo-5- (trifluoromethyl) pyridine-2-carboxylic acid. 80 g was obtained as white crystals.

(3) To 13 ml of 1,2-dichloroethane, 4.0 g of 3-iodo-5- (trifluoromethyl) pyridine-2-carboxylic acid, 2.3 g of thionyl chloride and 92 mg of N, N-dimethylformamide were added at 75 ° C. Stir for 2 hours. The reaction solution was returned to room temperature, the liquid obtained by distilling off the solvent under reduced pressure was added to 13 ml of ethanol at 0 ° C., and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, the solvent of the reaction solution was distilled off under reduced pressure, 15 ml of water was added, the mixture was extracted twice with ethyl acetate, the organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent: n-hexane / ethyl acetate = 9/1) to give 3-iodo-5- (trifluoromethyl) pyridine- 4.05 g of ethyl 2-carboxylate was obtained as a yellow liquid. Its ^{1 H-NMR δppm (Solvent:} CDCl 3 / 400MHz) is, 1.42 (3H, t, J = 7.2Hz), 4.49 (2H, q, J = 7.2Hz), 8.44 (1H, s), 8.84 (1H , s).

(4) 955 mg of sodium ethoxide was added to a mixed solution of 4.0 g of ethyl 3-iodo-5- (trifluoromethyl) pyridine-2-carboxylate, 1.46 g of cyclopropyl methyl ketone and 23 ml of tetrahydrofuran (dehydrated) at room temperature. Stir for 15 minutes. After completion of the reaction, the reaction mixture was acidified with 1N hydrochloric acid, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and evaporated under reduced pressure to remove crude 1-cyclopropyl-3- [ 3-Iodo-5- (trifluoromethyl) pyridin-2-yl] propane-1,3-dione was obtained as a liquid.
(5) The total amount of the crude liquid 1-cyclopropyl-3- [3-iodo-5- (trifluoromethyl) pyridin-2-yl] propane-1,3-dione obtained in (4) To a mixed solution of acetic acid (23 ml), 3-amino-1H-1,2,4-triazole (1.02 g) was added, and the mixture was stirred at 100 ° C. overnight. After completion of the reaction, the solvent was distilled off under reduced pressure, water was added to the obtained residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and then dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: n-hexane / ethyl acetate = 1/1) to obtain 1.7 g of the desired product as white crystals.

Synthesis Example 17
Of 3-chloro-2- (5-methyl [1,2,4] triazolo [1,5-a] pyrimidin-7-yl) -5- (trifluoromethyl) isonicotinate (Compound No. 98) Composition
(1) Heating a mixed solution of 500 mg of methyl 2,3-dichloro-5- (trifluoromethyl) isonicotinate, 0.66 ml of tributyl (1-ethoxyvinyl) tin, 216 mg of tetrakis (triphenylphosphine) palladium and 10 ml of toluene The reaction was carried out for 5 hours under reflux. The reaction solution was concentrated under reduced pressure, 1 ml of 6N hydrochloric acid was added to a mixed solution of the obtained residue and 5 ml of tetrahydrofuran, and the mixture was heated to reflux for 2 hours. After completion of the reaction, 3 ml of water was added, and the mixture was extracted with ethyl acetate. The residue was purified by silica gel column chromatography (eluent: n-hexane / ethyl acetate = 6/1), and 307 mg of methyl 2-acetyl-3-chloro-5- (trifluoromethyl) isonicotinate was obtained as a colorless oil. Got as. Its ^{1 H-NMR δppm (Solvent:} CDCl 3 / 400MHz) is, 2.72 (3H, s), 4.02 (3H, s), was 8.84 (1H, s).
(2) Methyl 2-acetyl-3-chloro-5- (trifluoromethyl) isonicotinate (307 mg) and N, N-dimethylacetamide dimethyl acetal (0.41 mg) were reacted in 5 ml of toluene at 100 ° C. for 4 hours. . The reaction mixture was concentrated under reduced pressure, and the resulting residue was dissolved in 3 ml of acetic acid, 100 mg of 3-amino-1H-1,2,4-triazole was added, and the mixture was heated to reflux for 17 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: n-hexane / ethyl acetate = 1/5) to obtain 138 mg of the desired product.

Synthesis Example 18
7- [4-Amino-3-chloro-5- (trifluoromethyl) pyridin-2-yl] -5-methyl [1,2,4] triazolo [1,5-a] pyrimidine (Compound No. 114) Synthesis of
(1) Methyl 3-chloro-2- (5-methyl [1,2,4] triazolo [1,5-a] pyrimidin-7-yl) -5- (trifluoromethyl) isonicotinate 502 mg and methanol 3 ml To the mixed solution was added 0.32 ml of 10N sodium hydroxide and reacted at 55 ° C. for 2 hours. The reaction solution was concentrated under reduced pressure, and 6N hydrochloric acid was added to the resulting residue to make it acidic (pH = 3-4). Extracted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, and evaporated under reduced pressure to remove 3-chloro-2- (5-methyl [1,2,4] triazolo [1 , 5-a] pyrimidin-7-yl) -5- (trifluoromethyl) isonicotinic acid 407 mg was obtained as a solid. Its ^{1 H-NMR δppm (Solvent:} DMSO-d 6 / 400MHz) is, 2.73 (3H, s), 7.64 (1H, s), 8.63 (1H, s), was 9.28 (1H, s).
(2) 3-chloro-2- (5-methyl [1,2,4] triazolo [1,5-a] pyrimidin-7-yl) -5- (trifluoromethyl) isonicotinic acid 237 mg, tert-butanol To a mixed solution of 0.24 ml and toluene 5 ml, 0.18 ml of diphenylphosphoric acid azide and then 0.13 ml of triethylamine were added and heated to reflux for 5 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel chromatography (eluent: methanol / ethyl acetate = 1/40) to obtain 55 mg of the desired product.

Synthesis Example 19
7- (3-Chloro-4-iodo-5- (trifluoromethyl) pyridin-2-yl) -5-methyl [1,2,4] triazolo [1,5-a] pyrimidine (Compound No. 115) Synthesis of 7- (4-amino-3-chloro-5- (trifluoromethyl) pyridin-2-yl) -5-methyl [1,2,4] triazolo [1,5-a] pyrimidine 55 mg, iodine 82 mg And the mixed solution of 5 ml of acetonitrile was cooled to 0 ° C., and 0.02 ml of tert-butyl nitrite was added dropwise. After completion of dropping, the reaction solution was warmed to room temperature and stirred for 12 hours. After completion of the reaction, 0.5 ml of an aqueous sodium thiosulfate solution was added and stirred for another 30 minutes. 5 ml of water was added, extracted twice with ethyl acetate, the organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel chromatography (eluent: n-hexane / ethyl acetate = 1/1) to obtain 33 mg of the desired product as pale yellow crystals.

Representative examples of the compounds of formula (I) are listed in Table 1. In Table 1, No. indicates the compound No., Me is methyl, Et is ethyl, n-Pr is normal propyl, i-Pr is isopropyl, i-Bu is isobutyl, and t-Bu is tertiary. Ri-butyl, sec-Bu represents secondary butyl, Ph represents phenyl, and the temperature indicated as a physical property is the melting point. However, dec indicates that decomposition occurred at that temperature. Table 2 shows ¹ H-NMR for some of the compounds of formula (I). These compounds can be synthesized based on the above-described Synthesis Examples 1 to 19 or various production methods of the compound of the present invention described above.

Next, test examples are described.
Test Example 1 Effect test on peach aphid Japanese radish leaves were inserted into a test tube containing water, and about 20 first-instar larvae were released on the leaves. The next day, after counting the number of larvae parasitic on the radish leaves, the parasitic radish leaves were immersed in a chemical solution adjusted to a concentration of 200 ppm of the present compound for about 10 seconds. After the chemical solution was air-dried, it was left in a constant temperature room at 25 ° C. with illumination. Five days after the treatment, the viability of the peach aphid was determined, and the mortality rate was determined by the following formula. The detached insects and abnormal insects were regarded as dead insects. When the compound Nos. 15, 20, 24, 26, 34, 41, 46, 49, 59, 65, 70, 74, 78, 79, 87, 95, 96, 104, 111 and 116 were tested, all This compound showed a death rate of 90% or more.
Death rate (%) = (1− (number of surviving insects / number of treated insects)) × 100

Test Example 2 Effect test on green planthopper Rice seedlings were immersed in a chemical solution adjusted to have a concentration of the present compound of 200 ppm for about 10 seconds. After the chemical solution was air-dried, the root was wrapped with wet absorbent cotton and placed in a test tube. Ten 10-year-old larvae of the green planthopper were released into this, and the tube mouth was covered with gauze and left in a constant temperature room at 25 ° C. Five days after the insect release, the dead planthopper was judged to be alive or dead, and the mortality rate was determined by the following formula. Compound No. 7, 12, 15, 17, 20, 21, 23, 24, 25, 26, 28, 34, 39, 41, 42, 47, 49, 50, 59, 62, 65, 66, 70, 71, 72, 74, 75, 77, 78, 79, 82, 83, 84, 86, 87, 88, 89, 90, 91, 92, 95, 96, 97, 99, 101, 103, 104, 106, When 107, 111, 112, 114, 115, 116 and 117 were tested, all the compounds showed a mortality rate of 90% or more.
Death rate (%) = (Number of dead insects / Number of dead insects) × 100

Test Example 3 Effect test on silver leaf whitefly A potted cucumber seedling infested with silver leaf whitefly 1-2 larvae was sprayed with a chemical solution adjusted to a concentration of 200 ppm of the compound of the present invention using a hand spray. After the chemical solution was air-dried, it was left in a constant temperature room at 25 ° C. with illumination. Seven days after the treatment, the number of old larvae was examined, and the control efficiency (%) was determined by the following formula. Compound No. 15, 20, 21, 24, 25, 26, 34, 49, 59, 74, 87, 88, 91, 92, 96, 97, 99, 101, 103, 106, 107, 111, 112, When 114, 115, 116 and 117 were tested, all compounds showed a control efficiency of 80% or more.

Control efficiency (%) = (1− (Ta × Cb) / (Tb × Ca)) × 100
Ta: old larvae after treatment in treated cucumber seedlings
Tb: Number of 1-2 instar larvae before treatment in treated cucumber seedlings
Ca: number of old larvae after treatment in untreated cucumber seedlings
Cb: Number of 1-2 instar larvae before treatment in untreated cucumber seedlings

Test Example 4 Medicinal Efficacy Test Using Dogs Against Phytophyllum Tick A dog (beagle, 8 months old) was administered a gelatin capsule containing 10 mg / kg body weight of the compound of the present invention. Immediately thereafter, about 50 young mites were collected from the ear of the dog. Let go through and artificially infest. After the treatment, observe the number of infestations, the number of drops, and the life and death of the fallen spider mites. As a result, the compound of the present invention drops or kills the parasitic spider mite.

Test Example 5 Medicinal Efficacy Test Using a Dog against a Cat Flea A gelatin capsule containing 10 mg / kg body weight of the compound of the present invention was administered to a dog (beagle, 8 months old), and immediately after that about 100 cat flea non-blood-sucking adults were covered in the back Let go on and let it infest. The compound of the present invention exhibits a hatching-inhibiting effect on the treated eggs of treated adults.
Test Example 5 Drug efficacy test using dogs against cat fleas

Next, formulation examples are described.
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 or more To make a wettable powder.

Formulation Example 2
(1) Compound of the present invention 5 parts by weight (2) Talc 60 parts by weight (3) Calcium carbonate 34.5 parts by weight (4) Liquid paraffin 0.5 parts by weight or more are uniformly mixed to obtain a powder.

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 dodecylbenzenesulfonate 2 parts by weight (5) Xylene 48 A mixture of more than parts by weight is uniformly mixed and dissolved to obtain an emulsion.

Formulation Example 4
(1) Clay 68 parts by weight (2) Sodium lignin sulfonate 2 parts by weight (3) Polyoxyethylene alkylaryl sulfate 5 parts by weight (4) White carbon 25 parts by weight A mixture of each component and the present compound Mix at a weight ratio of 4: 1 to make a wettable powder.

Formulation Example 5
(1) Compound of the present invention 50 parts by weight (2) Sodium alkylnaphthalene sulfonate formaldehyde condensate 2 parts by weight (3) Silicone oil 0.2 parts by weight (4) Water 47.8 parts by weight or more uniformly mixed (5) 5 parts by weight of sodium polycarboxylate (6) 42.8 parts by weight of anhydrous sodium sulfate are further added to the crushed stock solution, and the mixture is uniformly mixed, granulated and dried to obtain a granulated wettable powder.

Formulation Example 6
(1) Compound of the present invention 5 parts by weight (2) Polyoxyethylene octylphenyl ether 1 part by weight (3) Polyoxyethylene alkyl ether phosphate 0.1 part by weight (4) Granular calcium carbonate 93.9 parts by weight (1 ) To (3) are mixed uniformly in advance and diluted with an appropriate amount of acetone, and then sprayed onto (4) to remove acetone and form 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) Soybean oil 95.0 parts by weight or more are uniformly mixed and dissolved to give a trace amount of spray ( ultra low volume formulation).

Formulation Example 8
(1) Compound of the present invention 40 parts by weight (2) Polyoxyethylene tristyryl phenyl ether potassium 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 Part by weight (6) Water 50.7 parts by weight or more are uniformly mixed and pulverized to obtain an aqueous suspension.

Formulation Example 9
(1) Compound of the present invention 10 parts by weight (2) 80 parts by weight of diethylene glycol monoethyl ether (3) Polyoxyethylene alkyl ether 10 parts by weight or more of ingredients are mixed uniformly to obtain an aqueous solution.

The novel pyridyl-triazolopyrimidine derivatives or salts thereof of the present invention are useful as pest control agents.
The entire contents of the specification, claims, and abstract of Japanese Patent Application No. 2008-208708, filed on August 13, 2008, are incorporated herein as the disclosure of the specification of the present invention. Is.

Claims (10)

1. Formula (I):
   

   

   [Wherein R ¹ is alkyl optionally substituted with A, cycloalkyl optionally substituted with A, alkenyl optionally substituted with A, alkynyl optionally substituted with A, halogen atom, cyano, aryl , A heterocyclic group which may be substituted with alkyl, CH═NOR ² , CH═NNR ⁴ R ⁵ , COR ² , COOR ² , OR ² , S (O) _n R ³ , NR ⁴ R ⁵ or CONR ⁴ R ⁵ X is alkyl, alkenyl, alkynyl, aryl, heterocyclic group, halogen atom, haloalkyl, cyano, nitro, NR ⁴ R ⁵ , CONR ⁴ R ⁵ , S (O) _n R ³ , OR ² , COR ² or COOR ² ; A is a halogen atom, OR ² , S (O) _n R ³ , OS (O) _n R ³ , NR ⁴ R ⁵ , cyano, alkyl, cycloalkyl, aryl, heterocyclic group, SCH ₂ COOR ² , NHNR ⁴ R ⁵ , C OOR ² , nitro or —CH (CN) ₂ ; R ² is a hydrogen atom, alkyl, alkenyl, alkynyl, haloalkyl, cyanoalkyl, alkoxyalkyl, acetyl, benzyl or aryl; R ³ is alkyl or acetyl R ⁴ is a hydrogen atom or alkyl; R ⁵ is a hydrogen atom, alkyl, cycloalkyl, haloalkyl, COR ² , COOR ² , S (O) _n R ³ , CH ₂ CH ₂ OR ² or CH ₂ CN. M is an integer of 1 to 4, n is an integer of 0 to 2, and a pyridyl-triazolopyrimidine derivative represented by the formula:
2. R ¹ is alkyl optionally substituted with A, cycloalkyl optionally substituted with A, alkenyl optionally substituted with A, alkynyl optionally substituted with A, halogen atom, optionally substituted with alkyl heterocyclic ^group, CH = NOR ^2, CH = be ^{NNR 4 R 5, COR 2,} COOR 2, oR 2, S (O) n R 3, NR 4 R 5 or CONR ⁴ R ^5; X is an alkyl, aryl , Halogen atom, haloalkyl or OR ² ; A is a halogen atom, OR ² , S (O) _n R ³ , OS (O) _n R ³ , NR ⁴ R ⁵ , alkyl, cycloalkyl, heterocyclic group, NHNR ⁴ R ⁵ , COOR ² or nitro; R ² is a hydrogen atom, alkyl, haloalkyl or cyanoalkyl; R ³ is alkyl; R ⁵ is a hydrogen atom, alkyl, haloalkyl, COR ² or COOR ² Contract The pyridyl-triazolopyrimidine derivative or a salt thereof according to claim 1.
3. R ¹ is alkyl optionally substituted with A, cycloalkyl optionally substituted with A, alkenyl optionally substituted with A, CH═NOR ² , CH═NNR ⁴ R ⁵ , COR ² , COOR ² , NR The pyridyl-triazolo according to claim 2, which is ⁴ R ⁵ or CONR ⁴ R ⁵ ; A is OR ² , S (O) _n R ³ , OS (O) _n R ³ , NR ⁴ R ⁵ or nitro. A pyrimidine derivative or a salt thereof.
4. R ¹ is alkyl optionally substituted with A, cycloalkyl optionally substituted with A, alkenyl optionally substituted with A, CH═NOR ² , CH═NNR ⁴ R ⁵ , COR ² , COOR ² , NR ⁴ R ⁵ or CONR ⁴ R ⁵ ; A is OR ² , S (O) _n R ³ , OS (O) _n R ³ , NR ⁴ R ⁵ or nitro; R ⁵ is haloalkyl, COR ² or COOR The pyridyl-triazolopyrimidine derivative or a salt thereof according to claim ^2, which is 2.
5. The pyridyl-triazolopyrimidine derivative or a salt thereof according to claim 1, wherein X is OR ² .
6. A pest control agent comprising the pyridyl-triazolopyrimidine derivative of claim 1 or a salt thereof as an active ingredient.
7. An agricultural and horticultural pest control agent comprising the pyridyl-triazolopyrimidine derivative or a salt thereof according to claim 1 as an active ingredient.
8. An insecticide, acaricide, nematicide or soil insecticide containing the pyridyl-triazolopyrimidine derivative or its salt according to claim 1 as an active ingredient.
9. An insecticide or acaricide containing the pyridyl-triazolopyrimidine derivative or its salt according to claim 1 as an active ingredient.
10. A method for controlling pests by applying an effective amount of the pyridyl-triazolopyrimidine derivative or a salt thereof according to claim 1.