WO2004011467A1 - Triazolopyrimidine derivatives and fungicides for agricultural and horticultural use - Google Patents

Abstract

Fungicides for agricultural and horticultural use which contain novel triazolopyrimidine derivatives represented by the general formula (A), (B), or (C) and which exhibit high disease control activity and do not cause chemical damage: (A) (B) (C) wherein HetA-C is a heteroatom-containing five- or six-membered ring; XA-C is halogeno, cyano, or the like; RA and RA’ may be the same or different from each other and are each C1-10 alkyl, C2-10 alkenyl, C2-10 alkynyl, or phenyl; RB is an optionally substituted nitrogenous heterocycle attached at the nitrogen atom; and RC is C1-10 alkyl, C2-10 alkenyl, C2-10 alkynyl, C3-8 cycloalkyl, C4-10 cycloalkylalkyl, or aralkyl.

Description

Description ^: Triazolopyrimidine derivative and fungicide for agricultural and horticultural use

Technical field

 The present invention relates to a novel triazolopyrimidine derivative and a fungicide for agricultural and horticultural use comprising the derivative as an active ingredient. Background art.

 Heretofore, some triazolovirimidine derivatives similar in chemical structure to the present invention are known as shown below.

 (1) Japanese Patent Application Laid-Open No. 05-262773 describes that a triazo-opened pyrimidine represented by the following general formula has herbicidal activity.

(Wherein, R i _a represents a hydrogen atom, an alkyl group, an alkoxy group, an alkylthio group, a haloalkyl group, a haloalkoxy group, haloalkylthio group, a Shiano group, R _{2 a} represents an alkyl group, an alkoxy group, an alkylthio group , R _{3 a} represents an alkyl group, an alkoxy group, an alkylthio group, a haloalkyl group, c port alkoxy groups, haloalkylthio groups.)

(2) WO 99/41255 describes that a triazolopyrimidine derivative represented by the following general formula has a bactericidal activity.

(Wherein, R _b is an optionally substituted alkyl group, an alkenyl group, Arukini group, alkadienyl group, § Li Ichiru group, a cycloalkyl group or a consequent Roaruke two group, R _{2 b} is a hydrogen atom, halogen atom, hydroxy group, an an alkoxy _{group, R 3 b, R 4 bN} R 5 b, R 6 b , and: _{7 b} is, its is it independently hydrogen atom, a halogen atom, an alkyl group, an alkoxy group , Represents a nitro group or a cyano group.)

 (3) EP 2 153 382 discloses that triazolopyrimidine derivatives represented by the following general formula have bactericidal activity.

(In the formula, represents an unsubstituted or substituted alkyl group, an unsubstituted or substituted aralkyl group, an unsubstituted or substituted aryl group, etc., and R _{2 C} and R _{3 c} represent a hydrogen atom, an alkyl group, an aryl group, A represents a nitrogen atom, CR _4c , and R _4c represents a hydrogen atom, a halogen atom, or an alkyl group.)

 (4) International Patent Publication WO 00/44754 describes that a triazolopyrimidine derivative represented by the following general formula has an activity of suppressing fat accumulation in the human body.

n4d ヽ (Expressed in the formula, R _ld is a hydrogen atom, an alkyl group, an alkenyl group, R _{2 d} and R _{3 d} represents a hydrogen atom, a halogen atom, an alkyl group, a etc. alkenyl group, R _{4 d} is a hydrogen atom, Represents an alkyl group, etc., R _{5 d} represents an alkyl group, an alkenyl group, etc., and A represents a nitrogen atom, CH, etc.)

 (5) U.S. Pat. No. 5,593,996 describes that a triazolopyrimidine derivative represented by the following general formula has bactericidal activity.

Man

(Wherein, R _ie represents alkyl group, alkenyl group, cycloalkyl group, and heterocyclic Shikimoto a, R _2e represents a hydrogen atom, an alkyl group, or, together with _e and R _{2 e} is adjacent nitrogen atom Represents a heterocyclic group, R _3e represents an aryl group, and R _4e represents a hydrogen atom, a halogen atom, or an alkylamino group.)

(6) WO 01/96341 describes a method for producing a triazolopyrimidine-1 7-ylidene derivative using a triazolopyrimidine derivative represented by the following general formula as a raw material. Have been. Nevertheless, among the bets Riazoropiri thymidine derivative represented by the following general formula, derivative R _{2 f} is a complex璟is a specific example is not disclosed.

(Expressed in the formula, R _lf is a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, a haloalkyl group, a cycloalkyl group, phenyl group, naphthyl group, and heterocyclic Shikimoto a, R ₂ f Hue group, a cycloalkyl Alkyl group, heterocyclic group Represents, R _{3 f} represents a halogen atom, an amino group, an alkoxy group, a haloalkoxy group, and alkylamino group. )

 However, the compounds described in the above literature are shown in later test examples and have insufficient bactericidal activity against diseases in the field of agriculture and horticulture, have little therapeutic effect, and cause phytotoxicity to crops. Therefore, it is practically unsatisfactory. Therefore, there is a demand for an agricultural and horticultural fungicide containing a novel compound different from conventional drugs. DISCLOSURE OF THE INVENTION An object of the present invention is to provide a novel compound meeting the above-mentioned demands and a fungicide for agricultural and horticultural use using the same.

 The present inventors have synthesized many compounds and intensively studied their usefulness in order to achieve the above object. As a result, a novel triazolopyrimidine derivative with a specific structure has a broad control spectrum and a high control effect as an agricultural and horticultural fungicide, and depending on the type of disease, has both preventive and therapeutic effects It has been found to have high disease control activity.

 That is, the present invention is as follows.

(1) General formula (A),, N, _N A ^ H _e t _A

N people χ _Α

 (A)

 [Where,

H et _A denotes a 5- or 6-membered ring containing a hetero element, wherein these rings are a halogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, May be substituted with a C1-C6 haloalkyl group or a C2-C6 alkoxyalkyl group,

X _A is a halogen atom, Shiano group, C 1 through C 6 alkoxy group, C l to C 6 alkylthio group, C. 1 to C 6 alkylsulfinyl group, C 1 through C 6 alkylsulfonyl group, C 1 through C 6 alkyl Represents an amino group or a C 1 -C 6 alkoxycarbonyl group, and

 ! ^ び! ^^^ represents the same or different, C 1 -C 10 alkyl group, C 2 -C 10 alkenyl group, C 2 -C 10 alkynyl group or phenyl group (the alkyl group, alkenyl group, alkynyl group And a phenyl group are a halogen atom, a C1-C6 alkyl group, a C1-C6 alkyl group, a C1-C6 alkoxy group, a C1-C6 alkylthio group, a C1-C6 alkoxycarbonyl group. And may be substituted with one or more groups selected from the group consisting of carboxyl groups). ] The triazolopyrimidine derivative represented by these.

(2) The Het _A is represented by the following general formula Hetet _5.

(Where R ₂ and R ₃ are the same or different and represent a hydrogen atom, a C 1 -C 6 alkyl group, a C 1 -C 6 alkoxy group, a C 1 -C 6 haloalkyl group, or a halogen atom) Represents any group,

X _A represents a halogen atom, and

R _A and R _A , are the same or different from each other, are a C 1 -C 10 alkyl group, a C 2 -C 10 alkenyl group or a C 2 -C 10 alkynyl group (the alkyl group, the alkenyl group and The alkynyl group may be substituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 haloalkyl group)

The triazolopyrimidine derivative according to (1), which is characterized in that:

(3) the the He t _A is characterized in that it is a group table in the the He t have H et ₆ or H eti _2, preparative Riazoropiri midges down derivative according to (2). '

 (4) General formula (B)

[Where,

Het _B represents a 5- or 6-membered ring containing a hetero element, which is a halogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkyl group or a C2. ~ C 6 alkoxyalkyl group may be substituted,

X _B is halogen atom, Shiano group, C 1 through C 6 alkoxy group, C l ~ C 6 alkylthio group, C. 1 to C 6 alkylsulfinyl group, C. 1 to C 6 alkylsulfonyl group, C 1 ~ C 6 Arukiruamino A C 1 -C 6 alkoxycarbonyl group; and R _B is attached at the nitrogen atom, a nitrogen-containing heterocyclic ring which may be substituted. ]

A triazolopyrimidine derivative represented by the formula:

• (5) The Het _B represents any of the groups represented by the above general formula Hetet ₁₅ , and

X _B represents a halogen atom

The triazolobirimidine derivative according to (4), which is characterized in that:

(6) the the He t _B is characterized in that it is a group table in俞記the He t have H et ₆ or H et _2, preparative Riazoropiri midges down derivative according to ■ (5).

 (7) General formula (C)

 (C)

[Where,

H et _c represents a 5- or 6-membered ring containing a hetero element, and these 5- or 6-membered rings are a halogen atom, a C1-C6 alkyl group, a C1-C.6 alkoxy group, May be substituted by a group selected from the group consisting of C1 to G6 haloalkyl groups and C2 to C6 alkoxyalkyl groups,

_Xc represents a halogen atom, a cyano group, a C1-C6 alkoxy group or a C1-C6 alkylthio group, and.

R _c is, C 1 through C 10 alkyl group, C 2~ C 10 alkenyl group, C 2 ~C 1 0 alkynyl group, C 3 ~ C 8 cycloalkyl group, C4 ~ C 10 shea click port alkyl group or Ararukiru A benzene ring of the aralkyl group may be substituted with a halogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group or a C1-C6 alkylthio group. No. ]

 A triazolopyrimidine derivative represented by the formula:

(8) said H e t. _C is characterized by a group represented by the general formula H et, preparative Ria triazolopyrimidine derivative according to (7).

(9) A fungicide for agricultural and horticultural use, comprising the triazolopyrimidine derivative according to any one of (1) to (8) as an active ingredient. Formula (A;), Formula (B), Formula (C) or the general formula H etj ~H eti ₅ on the base is an alkyl group or a haloalkyl group, an alkoxy group, a haloalkoxy group, an alkylthio group The alkyl moiety of the alkoxycarbonyl group or the alkylamino group may be linear or branched.

In the general formula (A), H et _A or in the general formula (B), H et _B is an arbitrary 5-membered or 6-membered ring containing a hetero element within {}, preferably, the general formula H a ring represented by any one of Eteti _5, more preferably the ring represented by the He t physician 116 seven ₆ or ¾ [6 _"1 1 _2.

In the general formula (C), H et _c is an arbitrary 5- or 6-membered ring containing a hetero element in the ring, and is preferably any ring represented by the following general formula. Yes, and more preferably, Het! Is a ring represented by

, Ν

NS ヽ SS

Halogen atoms as R ₂ or R ₃ on Het _A , Het _B or Het _c , or on Het to Het ₅ include chlorine, bromine, iodine and fluorine atoms. And C 1 -C 6 alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, isobutyl, sec-butyl, n- Examples include a pentyl group, an isoamyl group, and an n-hexyl group. Examples of the C 1 -C 6 alkoxy group include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, and a sec-butoxy group. Group, t-butoxy group, isobutoxy group and isohexyloxy group. Examples of the C 1 -C 6 haloalkyl group include trifluoromethyl group, difluoromethyl group, trichloromethyl group, dichloromethyl group, and fluoromethylyl. Group, chloromethyl group, chloromethyl group, bromomethyl group, bromomethyl group, pentafluoroethyl group, 2,2,2-trifluoroethyl group, pentachloroethyl group, etc., and the C2-C6 alkoxyalkyl group includes methoxymethyl group. Group, ethoxymethyl group, n-propoxymethyl group, isopropogishethyl group, n Butoxymethyl group, sec - Butokishime butyl group, t Butokishimechiru group, I Su Wu butoxy methyl group, such as n- butoxy Echiru group.

In the general formula (A), the C 1 -C 10 alkyl group represented by R _A or R _A , is a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec group. —Butyl group, t-butyl group, n-pentyl group, isoamyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group and n-decyl group, and C 2 Examples of the -C 10 alkenyl group include a vinyl group, an aryl group, a 1-butenyl group, a 2-butenyl group, a 1-isobutenyl group, a 3-methyl-2-butenyl group, a 1-pentenyl group, a 1-hexenyl group, and a 1-hexenyl group. And a C 2 -C 10 alkynyl group such as ethynyl group, 2-propynyl group, 2-butynyl group, 3-butynyl group, 5-pentynyl group, 3,3-dimethyl-1-butynyl Group, 4-methyl-1-pen Such alkenyl groups and 7 Okuchiniru group. Examples of the halogen atom which is substituted with one or more hydrogen atoms on the alkyl group, alkenyl group, alkynyl group or phenyl group represented by R _A and R _A ′ include a chlorine atom, a bromine atom, an iodine atom and a fluorine atom. And as the C1-C6 alkyl group, A methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a t-butyl group, an isobutyl group, a sec-butyl group, an n-pentyl group, an isoamyl group, and an n-hexyl group. C1-C6 haloalkyl groups include trifluoromethyl, difluoromethyl, trichloromethyl, dichloromethyl, fluoromethyl, chloromethyl, odomethyl, promomethyl, penfluorofluorethyl and penchlorochloroethyl. Examples of the C 1 -C 6 alkoxy group include a methoxy group, an ethoxy group, an I-propoxy group, an isopropoxy group, an n-butoxy group, a sec-butoxy group, a t-butoxy group, an isobutoxy group and a And an isohexyloxy group. Examples of the C1-C6 alkylthio group include a methylthio group, Ethylthio group, n-propylthio group, isopropylthio group, n-butylthio group, sec-butylthio group, t-butylthio group, isoptylthio group, and isohexylthio group, and the like. Toxoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, sec-butoxycarbonyl, t-butoxycarbonyl, isobutoxycarbonyl and isohexyloxy And a carbonyl group.

In the above general formula (Β ·), R _B is an optionally substituted nitrogen-containing heterocyclic ring which is bonded to triazolopyrimidine and a nitrogen atom, and is preferably the following nitrogen-containing heterocycle. Rings. — Me

In the general formula (C), the C 1 to C 10 alkyl group as R _c includes a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, Isobutyl, sec-butyl, t-butyl, n-pentyl, isoamyl, n-hexyl, n-heptyl, 'n-octyl, n-nonyl and n-decyl No. Examples of the C 2 -C 10 alkenyl group include a vinyl group, an aryl group, a 1-butenyl group, a 2-butenyl group, a 1-isobutenyl group, a 3-methyl-2-butenyl group, a 1-pentenyl group, and a 1-hexenyl And a 1-octenyl group. Examples of the C 2 -C 10 alkynyl group include ethynyl group, 2-propynyl group, 2-butynyl group, 3-butynyl group, 5-pentynyl group, 3,3-dimethyl-1-butynyl group, 4 -Methyl-1-pentynyl group and 7-octynyl group. Examples of the C3-C8 cycloalkyl group include a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like. Examples of the C4-C10 cycloalkylalkyl group include a cyclopropylmethyl group, a cyclopropylethyl group, a cyclobutylmethyl group, a cyclopentylmethyl group, a cyclohexylmethyl group, a cyclohexylethyl group, and the like. Examples of the aralkyl group include a pendyl group, a monophenyl group, a -phenyl group, a 3-phenylpropyl group and a 4-phenylbutyl group. Examples of the aralkyl group having a halogen atom substituted on the benzene ring represented by R _c in the general formula (C) include a 2-chloropentyl group, a 3-chlorobenzene group, a 4-chlorobenzyl group, and a 2-chlorobenzene group. 6-Fluoropendyl group, 2,6-dichlorobenzyl group, 2,3-dichlorobenzyl group, 2,4-dichlorobenzyl group, 3,4-dichlorobenzyl group, 3-bromobenzyl group, 2-Fluoro benzyl group, 3-Fluoro benzyl group, 4-Fluoro benzyl group, 2,6-Difluoro benzyl group, 2,5-Difluoro benzyl group, 3,4-Difluoro benzyl group Examples include a benzyl group, a 3,5-difluorobenzyl group, a 4-chloro-phenylene group and a 4-chloro-phenylene group. Aralkyl groups having a benzene ring substituted with a C 1 -C 6 alkyl group include 2-methylbenzyl group, 3-methylbenzyl group, 4 monomethylbenzyl group, 2,4-dimethylbenzyl group, 3,4-dimethylbenzyl group, 2,4,6—trimethylbenzyl group, 4-ethylbenzyl group, 4-isopropylbenzyl group, 2,4,6 —Triisopropylbenzyl group, p-t-butylbenzyl group, and 3,5-di-t-butylbenzyl group. Examples of the aralkyl group in which the benzene ring is substituted with a C1-C6 alkoxy group include a 2-methoxybenzyl group, a 3-methoxybenzyl group, a 3,4-dimethoxybenzyl group, and a 3,5-dimethoxybenzyl group. , 3-Methoxy- 4-ethoxybenzyl, 4-ethoxybenzyl, 4-n-propoxybenzyl, 4-isopropoxybenzyl, 4-n-butoxybenzyl, 4-sec-butoxybenzyl, Examples include 4-isobutoxypentyl group, 4-t-butoxybenzyl group and 4-isohexyloxybenzyl group. Aralkyl groups in which the benzene ring has been substituted with a C1-C6 alkylthio group include 2-methylthiobenzyl, 3-methylthiobenzyl, 4-methylthiobenzyl, 4-ethylthiobenzyl, and 4-n —Propylthiobenzyl, 4-isopropylthiobenzyl, 4-η-butylthiobenzyl, 4-sec—Butylthiopendyl, 4-isobutylthiobenzyl, 4-t-butylthiobenzyl, and 4-t-butylthiobenzyl Cishexylthiobenzyl group and the like.

As the halogen atom is a X _c in X _B or the general formula X _A, general formula in the formula (A) (B) (C ), a chlorine atom, a bromine atom, and an iodine atom and fluorine atom. Examples of the C 1 -C 6 alkoxy group include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, a sec-butoxy group, a t-butoxy group, an isobutoxy group, an n-pentyloxy group, and a And a so-hexyloxy group. C1-C6 alkylthio groups include methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, sec-butylthio, t-butylthio, isobutylthio and isohexyl. And a silthio group.

The C 1 ~ C 6 alkylsulfinyl group is X _B in X _A or formula In Formula (A) (B), methylsulfinyl group, E Ji Rusurufieru group, n- propyl sulfinyl group, isopropyl sulphates Iniru group , N-butylsulfinyl, sec-butylsulfinyl, t-butylsulfinyl, isobutylsulfinyl, and isohexylsulfinyl. C1-C6 alkylsulfonyl groups include methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, sec-butylsulfonyl, t-butylsulfonyl, isobutyls And a ruphonyl group and an isohexylsulfonyl group. The C 1 -C 6 alkylamino group may be a monoalkylamino group or a dialkylamino group. Examples of the alkyl moiety include methyl, ethyl, n-propyl, isopropyl, and n-alkyl. Butyl, isobutyl, isohexyl and the like. Examples of the alkoxy moiety of the C 1 -C 6 alkoxycarbonyl group include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, t-butoxy, isobutoxy, n-pentyloxy and isohexyloxy. Is mentioned.

 Tables 1 to 10 show specific examples of the triazolopyrimidine derivative of the present invention represented by the general formula (A), and specific examples of the triazolopyrimidine derivative of the present invention represented by the general formula (B). Tables 11 to 22 show specific examples of the triazolopyrimidine derivative represented by the general formula (C) according to the present invention in Tables 23 to 25. Further, Table 26 shows specific examples of compounds that can be intermediates of these derivatives (compounds represented by the general formula (1) in Scheme 1 described below).

In the table, "Me" represents a methyl group, "Et" represents an ethyl group, "nPr" represents an n-propyl group, "iPrj represents an isopropyl group, and" nBu " Is n-butyl group, “iBu” is isoptyl group, “nPenI is n-pentyl Represents a group. The compound No. in the table is also referred to in the following Examples and Test Examples.

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Replacement paper (Kaikai ¾26) —The triazopyrimidine derivative represented by the general formula (A), (B) or (C) can be produced by the method shown in Scheme 1 below.

 Scheme 1

(Where Halo represents a halogen atom, Het _A , Het _B and Hetc and RAS RA ', HB, and' RC are the same as described above, Het represents any of Het _A , Het _B or Hetc, and W represents Y represents a hydrogen atom or an alkali metal atom such as sodium or potassium, and Y represents a cyano group, a C1-C6 alkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 group. Alkylamino group or C1-C6 alkoxy group.)

—Step (Step 1) of reacting the compound of the general formula (1) with the compound of the general formula (2) or reacting the compound of the general formula (1) with the compound of the general formula (4) The step (Step 3) preferably comprises adding 1 equivalent of the compound of the general formula (2) or the compound of the general formula (4) to the compound of the general formula (1), and adding 1.0 to 2.5 equivalents of a base. In the presence of a suitable organic solvent. The reaction temperature is 20 to 150 ° C, and the reaction time is 1 to 8 hours. Examples of the base include organic bases such as triethylamine and N, N-getyl di'phosphorus; and inorganic bases such as sodium carbonate, sodium hydrogencarbonate, carbonated lime, and oily hydrogenated sodium. Examples of the organic solvent include hydrocarbons such as toluene and xylene; halogenated hydrocarbons such as chloroform and benzene; ethers such as dioxane and tetrahydrofuran; nitriles such as acetonitrile; Amides such as dimethylformamide and dimethylacetamide and dimethylsulfoxide can be used. After completion of the reaction, water and an organic solvent such as benzene, toluene, and chloroform are added to the reaction mixture for extraction.The organic solvent layer is dehydrated with anhydrous sodium sulfate, magnesium sulfate anhydrous, etc., and the solvent is distilled off. Perform normal processing such as If necessary, purify by operations such as chromatography. The compound of the general formula (2) and the compound of the general formula (4), which are the starting compounds for this reaction, are commercially available products or are known compounds that can be easily produced by known methods.

The 5-halogen triazolopyrimidine derivative (A ⁵ ) or (Β ′) thus obtained is converted into an alcohol, alkylamine or a compound represented by the general formula (3) in the presence of a base. Producing a triazolopyrimidine derivative represented by the general formula (A ") or (B") by reacting the compound with a metal or the like or with an alkali metal cyanide (Step 2 or Step 4). Can be. The compound represented by the general formula (3), which is a starting compound for this reaction, is a known compound that is commercially available or can be easily produced by a known method. Examples of the compound represented by the general formula (3) include, for example, methyl alcohol, ethyl alcohol, isopropyl alcohol, methylamine, and ethylamine. , Methyl mercaptonate sodium, sodium cyanide, potassium cyanide and the like.

 In the step (Step 5) of reacting the compound represented by the general formula (1) with the compound represented by the general formula (5), preferably, one equivalent of the compound (5) is added to the compound (1). The reaction is carried out in a suitable organic solvent in the presence of 0.01 to 1.0 equivalent of a transition metal such as palladium or nickel. By this reaction, among the compounds represented by the general formula (C), a 5-halogentriazolopyrimidine derivative (compound (C ′)) in which X is a halogen atom is obtained. As the organic solvent, hydrocarbons such as toluene and xylene or ethers such as dioxane and tetrahydrofuran can be used.The reaction temperature is 20 to 150 ° C., preferably used. The temperature is close to the boiling point of the organic solvent used, and the reaction time is 1 to 8 hours.

 Further, reacting the obtained 5-halogenated liazolopyrimidine derivative represented by the general formula (C,) with an alcohol or a thiol in the presence of a base or with a metal cyanide or the like. Thus, the triazolopyrimidine derivative represented by the general formula (C) of the present invention can be produced. Examples of the base used in the present reaction include, for example, organic bases such as triethylamine, N, N-getylalanine and the like. And inorganic bases such as sodium hydroxide, sodium carbonate, sodium bicarbonate, potassium carbonate or sodium hydride.Examples of metal cyanides include, for example, sodium cyanide, potassium cyanide, etc. Is mentioned.

 After the reaction is completed, water and an organic solvent such as benzene, toluene or chloroform are added to the reaction solution for extraction, and the mixture is separated.After that, the organic solvent layer is dehydrated with anhydrous sodium sulfate or anhydrous magnesium sulfate. Perform normal processing such as distilling off the solvent. If necessary, purify by chromatography, recrystallization, etc.

Compound (5), which is one of the starting compounds in the above-mentioned reaction, is a known compound, and is obtained by using a commercially available product or by producing it by a known method. Can be used ...

 The dihalogentriazolo pyrimidine derivative represented by the general formula (1) in the above scheme 1 can be produced according to the following scheme 2.

 Scheme 2

(Where Halo represents a halogen atom, R represents a C1-C10 alkyl group, and Het represents any of Bet _A , Het _B or Hetc, where Het _A , Het _B and Hetc are the same as described above. That is, the compound represented by the general formula (1) is composed of a malonic ester derivative represented by the general formula (7) and a 3-amino-1,2,4 represented by the general formula (6). The compound can be produced by condensing triazole to obtain a compound represented by the general formula (8) and halogenating the compound. This reaction will be described separately in the following condensation step and halogenation step.

(Condensation step) In the step of reacting compound (7) with compound (6), one equivalent of compound (7) is preferably added to compound (6), and the reaction is performed in the presence of 1 to 5 equivalents of a base. The reaction is performed in an appropriate organic solvent according to Bases used in this reaction step include alkali metal alkoxides such as sodium methoxide, triethylamine, tri-n-propylamine, tri-n-butylamine, pyridine, dimethylaminoviridine, and N, N-ethylethylaniline. Organic bases, inorganic bases such as sodium carbonate, sodium hydrogen carbonate, and potassium carbonate. Organic solvents include hydrocarbons such as toluene and xylene, and halogenated compounds such as benzene Hydrocarbons, ethers such as dioxane and tetrahydrofuran, alcohols such as methanol, ethanol, n-butanol, amides such as dimethylformamide and dimethylacetamide, and dimethylsulfoxide. Can be used. A preferable reaction temperature for facilitating the above reaction is 20 to 150 ° C., preferably a temperature close to the boiling point of the organic solvent used, and a reaction time for the starting compound used. Although it varies depending on the catalyst, reaction temperature, etc., it is generally 1 to 8 hours. When the reaction is performed in this manner, compound (8) is obtained. This compound may be fractionated and used in the next reaction, but is preferably used as it is in the next reaction step.

 (Halogenation Step) In the step of halogenating the compound (8) obtained in the above reaction to obtain the compound (1), the reaction solution containing the compound (8) generated in the above step is added to the deoxidizing agent if necessary. The compound (8) may be reacted by adding 1 to 10 equivalents of a halogenating agent in the presence of the compound (8). Next, the reaction solution is subjected to a normal treatment such as distilling off the used solvent and excess halogenating agent, or, if necessary, purification by an operation such as chromatography and recrystallization. The desired compound (1) can be obtained. Examples of the deoxidizing agent that can be used in the nitrogenation step include organic bases such as triethylamine, tri-n-propylamine, tri-n-butylamine, pyridine, dimethylaminopyridine, N, N-jetylaniline, sodium carbonate, hydrogencarbonate and the like. Examples include inorganic bases such as sodium and potassium carbonate. Examples of the halogenating agent that can be used in the halogenation step include phosphorus oxychloride and phosphorus oxybromide. Since the halogenating agent also serves as a solvent, the reaction does not require a reaction solvent.However, when an organic solvent is used in the reaction, for example, hydrocarbons such as benzene and toluene, chlorobenzene, and chloroform are used. Halogenated hydrocarbons can be used. The reaction temperature of the halogenation is 50 to 150 ° C., and the reaction time is 1 to 10 hours.

Further, the obtained halogen triazolopyrimidine represented by the general formula (1) The compound is reacted in a suitable organic solvent by adding 1 to 10 equivalents of a halogenating agent to compound (1) in the presence of 0.05 to 2.5 equivalents of a base, if necessary. Thus, a hydrogen atom on Het can be replaced with a halogen atom. Examples of the halogenating agent that can be used in the reaction include chlorine, sulfuryl chloride, N-chlorosuccinimide, bromine, and N-promosuccinimide. Examples of bases that can be used in the reaction include organic bases such as triethylamine, tri-n-propylamine, tri-n-butylamine, pyridine, dimethylaminoviridine, N, N-ethylethylphosphorus, sodium carbonate, hydrogen carbonate and the like. Organic bases such as sodium and potassium carbonate can be used. The reaction temperature of the halogenation is 50 to 150 ° C, and the reaction time is 1 to 10 hours. As the organic solvent, hydrocarbons such as benzene and toluene, and halogenated hydrocarbons such as benzene and chloroform can be used _.

 The malonic ester derivative represented by the general formula (7) can be produced by the following method 3 (Method 1 to Method 3).

 Scheme 3

Method 1

(Ten)

 (In the formula, H et and R represent the same meaning as described above, and Z represents a halogen atom or a C 1 -C 10 alkoxy group.)

Method 2

(In the formula, Het and R represent the same meaning as described above, and L represents a leaving group such as a halogen atom, a toluenesulfonyl group, a methylsulfonyl group, etc.) Method 3

(Wherein, Ha 1 o, R, R ₂ and H ₃ represent the same meaning as described above, and A and B represent a nitrogen atom and CR i, or CR and a nitrogen atom, where R, Hereinafter, each of Method 1 to Method 3 will be described in detail.

(Method 1) The reaction between the compound represented by the general formula (9) and the compound represented by the general formula (10) is performed by adding 1 to 2 equivalents of the compound (10) to the compound (9). The reaction is carried out in a suitable organic solvent in the presence of 1 to 2 equivalents of a base as necessary. The reaction temperature is —70 to 150. C, and the reaction time is 1 to 8 hours. Examples of the base include alkali metal alkoxides such as sodium methoxide, organic bases such as triethylamine, N, N-getylaniline, and inorganic bases such as sodium carbonate, sodium hydrogencarbonate, sodium carbonate, and oily sodium hydride. And lithium diisopropylamine. Examples of the organic solvent include hydrocarbons such as toluene and xylene, halogenated hydrocarbons such as chloroform and benzene, ethers such as dioxane and tetrahydrofuran, and amines such as dimethylformamide and dimethylacetamide. And dimethylsulfoxide. After completion of the reaction, water and an organic solvent such as benzene, toluene, or chloroform are added to the reaction mixture for extraction.The organic solvent layer is dehydrated with anhydrous sodium sulfate, anhydrous magnesium sulfate, etc., and the solvent is distilled off. Perform normal processing such as If necessary, purify by chromatography, recrystallization, etc. The compounds represented by the general formulas (9) and (10), which are the starting compounds for this reaction, are known compounds, and may be obtained from commercial products or used, or produced by known methods. Can be used.

 (Method 2) The step of reacting the compound represented by the general formula (11) with the compound represented by the general formula (12) is performed in an amount of 1 to 2.5 equivalents of the compound represented by the formula (11). (12) is added, and the reaction is carried out in an appropriate organic solvent in the presence of 1.0 to 2. equivalents of a base, if necessary. The reaction temperature is 20 to 150 ° C, and the reaction time is 1 to 8 hours. Examples of the base include organic bases such as alkali metal alkoxides such as sodium methoxide, triethylamine, N, N-methylethylaniline, and inorganic bases such as sodium carbonate, sodium hydrogencarbonate, potassium carbonate, and oily sodium hydride. Can be used. Examples of the organic solvent include hydrocarbons such as toluene and xylene, halogenated hydrocarbons such as chloroform and benzene, ethers such as dioxane and tetrahydrofuran, and nitriles such as acetonitrile. Amides such as dimethylformamide and dimethylacetamide, and dimethylsulfoxide can be used. After completion of the reaction, water and an organic solvent such as benzene, toluene, and chloroform are added to the reaction solution for extraction.The organic solvent layer is dehydrated with anhydrous sodium sulfate, anhydrous magnesium sulfate, etc., and the solvent is distilled off. Normal processing such as is performed. If necessary, purify by chromatography or other procedures.

 The compounds represented by the general formulas (11) and (12), which are the starting compounds for this reaction, are known compounds, and may be obtained by using commercially available products or produced by known methods. Can be used.

(Method 3) The step of reacting the compound represented by the general formula (13) with the compound represented by the general formula (14) is performed in an amount of 1 to 2.5 equivalents of the compound (14) with respect to the compound (13). The reaction is carried out in a suitable organic solvent in the presence of 1.0 to 2.5 equivalents of a base, if necessary. The reaction temperature is 20 to 150 ° C, preferably, a temperature close to the boiling point of the organic solvent used, and the reaction time. W

49 is 1 to 8 hours. Examples of the base include alkali metal alkoxides such as sodium-toxide, organic bases such as triethylamine, N, N-ethylylaniline, sodium carbonate, sodium hydrogencarbonate, sodium carbonate, and sodium oil hydride. Inorganic bases can be used. Examples of the organic solvent include hydrocarbons such as toluene and xylene, halogenated hydrocarbons such as chloroform and benzene, ethers such as dioxane and tetrahydrofuran, nitriles such as acetonitrile, and the like. Amides such as dimethylformamide and dimethylacetamide and dimethylsulfoxide can be used. After completion of the reaction, water and an organic solvent such as benzene, toluene, and chloroform are added to the reaction mixture for extraction.The organic solvent layer is dehydrated with anhydrous sodium sulfate, anhydrous magnesium sulfate, etc., and the solvent is distilled off. Perform normal processing such as If necessary, purify by chromatography, recrystallization, etc.

 The compounds of the general formulas (13) and (14), which are the starting compounds for this reaction, are known compounds, and are obtained by using commercially available products or manufactured and used by known methods. be able to.

 The derivatives represented by the general formula (A), (B) or (C) include salts thereof. Examples of the salt include an inorganic acid salt such as hydrochloride and sulfate, and an organic acid salt such as acetate, oxalate and methyl sulfonate.

 The derivative represented by the general formula (A), the general formula (B) or the general formula (C) (hereinafter, also referred to as “the compound according to the present invention”) has a bactericidal activity. Thus, compositions containing one or more of the compounds according to the present invention can be used as fungicides. In particular, compositions containing one or more of the compounds according to the present invention can be used as agricultural and horticultural fungicides.

Among the compounds according to the present invention, preferred compounds as components of agricultural and horticultural fungicides are triazolopyrimidine derivatives shown in Tables 1 to 25, and more preferably, 31 is a triazolic pyrimidine derivative shown in FIG. Table 27 Compounds in Kakko in 7 to 31 The product numbers correspond to the compound numbers in Tables 1-25. '

Table 27

 5—Chloro-6— (3,5-dichroic 2-Chenyl) — Ί— (Ν—Methyl-1-21-methylpropylamino) 1,1,4-Triazolo [1,5a] pyrimidine (Compound N 0. A- 2)

 5—Chloro 6— (2,5-dichloro π 3 —Chenyl) 1 7— {N— (2-butenyl) 1-ethylamino} —1,2,4-triazolo [1,5a] pyrimidine (compound N 0. A— 2 1)

 5—Black mouth 6— (2,5-Dichloro-3-phenyl) 1 7— {N— (2-Methyl-2-propenyl) —ethylamino} —1,2,4—Triazolo [1,5a ] Pyrimidine (Compound N 0. A— 22)

 5-chloro-6- (2,5-dichloro-3-Chenyl) -1 7- {N- (2-butenyl) -1 2,2,2-Trifluoroethylamino} -1,2,4-tria Zoro [1,5a] pyrimidine (Compound No. A—23)

 5—Black D—6— (5—Black mouth 6—Ethyl-4—Pyrimidyl) -1Ί- (N-methyl-2-Methylprohirylamino) -1-1,2,4-Triazolo [1,5a] Pyrimidine (Compound N 0. A— 49)

 5-chloro-6- (5-chloro-1-6-methyl-4-pyrimidyl) 7- (N-methyl-2-methylpropylamino) 2,4-triazolo [1,5a] pyrimidine (compound A — 50)

 5-Chloro-6- (5-bromo-1-6-methyl-4-pyrimidyl) -1-7- (N-methyl-2-methylpropylamino) -1,2,4-trizolo [1,5a] pyrimidine (Compound N o. A— 52)

 5-chloro-1,6- (5,6-dimethyl-14-pyrimidyl) -17- (N-methyl-2-methylpropylamino) -1,2,4-triazolo [1,5a] pyri Midine (Compound N 0. A-57)

 5-chloro-6- (2,5-dimethyl-14-pyrimidyl) -17- (N-methyl-2-methylpropylamino) 1-1,2,4-triazolo [1,5a] pyrimidine (Compound N 0. A- 60)

 5—Chloro 6— (2-Methyl-1 5—Chloro-1-pyrimidyl) 1 7— (N-methyl-2-methylpropylamino) 1 1,2,4—Triazolo [1,5a] Pyrimidine (Compound No. A-64)

6- (1-Methyl-2-pyrrolyl) -17- (N-methyl-2-methylpropylamino) -1,2,4-Triazolo [1,5a] pyrimidine (compound Object N 0. A- 7 4) Table 28

 5-chloro-1-6- (2-methyl-5-chloro-4-thiazolyl) -17- (N-methyl-2-methylpropylamino) 1-1,2,4-triazolo [1,5a] pyrimidine (compound A — 8 4)

 5-chloro-1-6- (3,5-dimethyl-1-1-pyrazolyl) -17- (N-methyl-2-methylpropylamino) -1,2,4-triazolo [1,5a] pyri Midine (compound N 0. A— 99)

 5-Methylthio-1 6- (3,5-dimethyl-1-birazolyl) 1 7- (N-methyl-2-methylpropylamino) 1,2,4-Triazo D [1,5a] pyrimidine ( Compound No. A—102).

 5-cyano 6- (3,5-dimethyl-1-pyrazolyl) -7- (N-methyl-2-methylpropylamino) 1,2,4-triazolo [1,5a] pyrimidine (compound N 0. A- 1 0 5)

 6- (3-Ethyl-5-methyl-1 monopyrazolyl) -17- (N-Methyl-12-methylpropylamino) 1-1,24-Triazolo [1,5a] pyrimidine (Compound N o. A- 1 1 2)

 6- (3,4,5-trimethyl-1-pyrazolyl) -17- (N-methyl-2-methylpropylamino) 1-1,24-triazolo [1,5a] pyrimidine ( Compound N o. A— 1 16)

 5-chloro-6— (1,5-dimethyl-3-birazolyl) — —— (N-methyl 2-methylpropylamino) 1,1,2,4-triazolo [1,5a] pyrimidine (compound N 0.A- 1 2 4)

 5-chloro-1,6- (3,5-dichloro-2-enedyl) -17- (4-methyl-1 -piperidyl) 1,2,4-triazolo [1,5a] pyrimidine (compound Object N 0. B— .8)

 5—Black mouth 6— (3,5-Dichro mouth 1—Chenyl) 1 7— (4-ethoxycarbone 1-piperidyl) 1 1,2,4—Triazolo [1,5a] pyrimidine (Compound N 0. B— 11)

 6- (3-Chenyl) -17- (4-Methyl-1-piperidyl) —1,2,4-Triazolo [1,5a] pyrimidine (Compound No. B-16)

5—Chloro-6— (2,5-dichloro-3-Chenyl) -17— (4-Methyl-1-1-piperidyl) —1,2,4-Triazolo [1,5a] pyrimidine (Compound N 0.B -1 9)

'5-Chloro-6- (2,5-dichloro-1.-Chenyl) — Ί — (1 —Pyridyl) 1-1,2,4-Triazolo [1, .5a] pyrimidine (Compound N 0. B—2 3) Table 29

 5-chloro-1--6- (25-dichloro-1-3-enyl) -17- (4-methyl-11-piperazyl) 1-12,4-triazolo [1,5a] pyrimidine (compound N 0.B-24)

 5-Chloro-6- (25-Dichloro-3-Chenyl) -1 7- (4-ethoxycarbone 1-piperidyl) 1,2,4-Triazolo [1,5a] pyrimidine (Compound N 0.B-2 8)

 5-cyano 6- (25-dichlo-l-cenyl) 1 7- (4-methyl-1-pyridyl) 1 1, 2,4 Triazolo [1,5a] pyrimidine (compound N 0. B— 3 2)

 5—Black mouth— 6— (2,3,5—Trichrome mouth—4—Chenyl) — 7— (4—Methyl-1—Pyridyl) —1,2,4—Triazolo [1,5 a] Pyrimidine (Compound N 0. B-39)

 5—Chloro 6— (2,3,5 Triclo mouth 1—Chenyl) 1 7—

4-oxazine-1-4-yl) 1 1, 2,4—Triazolo [1,5a] pyrimidine (compound No. B-41)

 5-chloro-one 6- (2,5-jibu-mout 3-cynyl) -17- (4-methyl--1-piperidyl) 1-1,2,4-triazolo [1,5a] pyrimidine (compound Object N 0.B-4 3)

 5-chloro-6- (2-methyl-4-tritrifluoromethyl-6-pyrimidyl) -7- (4-methyl-1- 1-piperidyl)-1,2,4-triazolo [1,

5 a] Pyrimidine (Compound N 0. B-50)

 5—Black mouth 6— (5-Black mouth 6-methyl-1-41-pyridyl) — 7— (4-Methyl-1-piperidyl)-1,2,4—Triazolo “, 5 a] (Compound N 0. B— 57)

 5-chloro-6- (5-funoleo-6-methyl-4-pyrimidyl) -17- (4-methyl-11-piridyl) 1-1,2,4-triazolo [1,5a] pyrimidine (Compound N 0. B—60)

 5-chloro-6- (5-chloro-1-6-ethyl-4-pyrimidyl) -17- (4-methyl-1-piperidyl) 1-1,2,4-triazolo [1,5a] pyrimidine (compound N 0 B-6 1)

5-chloro-1-6- (5-chloro-6-isopropyl-1-pyrimidyl) -17- (4-methyl-1-piperidyl) 1-1,2,4-triazolo [1,5a] bilimidine ( Compound N 0. B— 6 2) Table 30

 5—Chloro 6— (5-Chloro 4-pyrimidyl) 1 7— (4-methyl-1—piperidyl) —1,2,4—triazolo [1,5a] pyrimidine (compound N 0 B-6 3)

 6- (5-bromo-6-methyl-1-pyrimidyl) 7- (4-methyl-1-1-1-pyridyl) 1-12,4-Triazolo [1,5a] pyrimid (Compound N 0. B-64)

 5-Chloro-6- (2-methyl. 5-fluoro-4-pyrimidyl) -1 7- (4-methyl-1 1-piperidyl) 1 124-triazolo [1,5a] pyrimidine (compound N o B-6 6)

 5—Black mouth 6— (2-Methyl 5—Black mouth 4-pyrimidyl) 2 7— (4—Methyl-1—Piperidyl) 1 1,2,4—Triazolo [1,5a] Pyrimidine ( Compound N o. B— 68)

 6- (5-Fluoro 6-Fluoromethyl-4-Pyrimidyl) — 7— (4-Methyl-1—Piperidyl) 1-1,2,4-Triazolo [1,5a] pyrimidine (Compound N 0 .B-7 2)

 6- (2,5-Dimethyl-4-pyrimidyl) — 1,4- (4-methyl-1-piperidyl) -1,2,4-Triazolo [1,5a] pyrimidine (Compound N 0 B— 7 6)

 6— (1—Methyl-1-2-pyrrolyl) — (— (4-Methyl-1-1—piperidyl) -1-1,2,4-Triazolo [1,5a] pyrimidine (compound N o B-9 3)

 5 _ 1-methyl-6- (1-methyl-1-5- 2-pyrrolyl) -1 7 "(4-methyl-1-piperidyl) 1,2,4-triazolo [1,5a] pyrimidine ( Compound N 0.B-97)

 5—Chloro-6— (2-Methyl-1-4-thiazolyl) -1 7— (4-Methyl-1-1-piperidyl) —1,2,4-triazolo [1,5a] pyrimidine (Compound No. B- 1 0 2)

 5—Chloro 6— (2-Methyl-1 5—Chloro1.4.1-thiazolyl) 1 7— (4-Methyl-1—piperidyl) 1 1,2,4-Triazolo [1,5a] pyri Mizine (Compound No. B-103).

5-chloro-1,6- (3,5-ditrifluoromethyl-1-pyrazolyl) -17-1,4-methyl-1-piperidyl 1,1,2,4-triazolo [1,5a] pyri Midine (Compound N 0. B— 1 15) Table 3 1

 5-Chloro-6- (3-trifluoromethyl-1-5-methoxyl-birazolyl) -17- (4-methyl-1-piperidyl) 1-1,2,4-Triazolo [1,5a] pyrimidine (compound N 0.B-1 2 4)

 5-chloro-6- (3,5-dimethyl-1-pyrazolyl) -17- (4-methyl-1-piperidyl) 1-1,2,4-triazolo [1,5a] pyrimidine (compound N 0.B-1 2 7)

 5-cyano 6- (3,5-dimethyl-1-pyrazolyl) -17- (4-methyl-1-piperidyl) 1,1,2,4-triazolo [1,5a] pyrimidine (compound N 0.B-1 3 3)

 5-Chloro-6- (3-ethyl-5-methyl-1-pyrazolyl) -17- (4-methyl-1-piperidyl) -11,2,4-triazolo [1,5a] pyrimidine (compound N 0.B -1 3 6)

 5-chloro-1,6- (3,4,5-trimethyl-1-1-pyrazolyl) -17- (4-methyl-1-piperidyl) -1,2,4-triazolo [1,5a] pyrimidine ( Compound N o. B— 1 3 8)

 5-Chloro-6— (3,5-dimethyl-1 4-chloro-1- 1-pyrazolyl) — Ί— (4-methyl-1-biperidyl) 1-1,2,4-triazolo [1,5a] pyrimidine ( Compound N o. B-1 4 1)

 6- (1,5-dimethyl-3-pyrazolyl) -17- (4-methyl-1-1-piperidyl) -1,2,4-triazolo [1,5a] pyrimidine (compound Object N 0.B-1 4 7)

 6- (3,5-Dimethyl-1-pyrazolyl) -17-cyclohexyl-1,2,4-1triazolo [1,5a] pyrimidine (Compound No. C-1)

5-Chloro-6- (3,5-dimethyl-1- 1-pyrazolyl) -17- (2-methylpropyl) 1-1,2,4-triazolo [1,5a] pyrimidine (compound N.C-5)

 5-Chloro-6- (3,5-dimethyl-1-pyrazolyl) -17- (1-methylbutyl) 1-1,2,4-triazolo [1,5a] pyrimidine (Compound No. C-6)

 6- (3,5-dimethyl-11-pyrazolyl) -17-cyclopropylpyrmethyl-1,2,4-triazolo [1,5a] pyrimidine (compound N.C-10)

5—Chloro— 6— (3,5-Dimethyl-1-Vilazolyl) -1 7—Benzyl-1,2,4-Triazolo [1,5a] pyrimidine (Compound N 0. C—11) The compounds according to the present invention can have excellent bactericidal activity against bacteria belonging to a wide variety of filamentous fungi. Therefore, the composition containing the compound according to the present invention as an active ingredient can be used for various diseases of agricultural and horticultural crops including petals, turf, etc. by foliage application, water application, soil application, seed treatment, or the like. Can be done.

The compounds according to the present invention have a particularly high controlling effect in controlling the diseases shown in Tables 32 to 34 described below.

Table 3 2

Kyupuri Udonko (Sphaerotheca fuliginea)

Gray power ^s bi (Bo trytis cin erea)

 囷 Sclerotinia sclerotiorm

 Scab (Cladosporium cucumerinum) Downy mildew (Pseudoperonospora cubensis) Plague (Pytophthora sp)

 Vine blight (Mycospaerella melonis)

 Vine harm! ] Disease (Fusarium oxysporu)

Eggplant powdery mildew (Sphaerotheca fuliginea)

 Gray mold (Bo trytis cin ere a)

Soot force ^¾ beauty's disease {Myco vellosiella na ttrassii) black blotch {Corynespora melongenae)

 Brown spot (Phomopsis vexans) Kingen Gray mold (Bo trytis cin erea)

 Sclerotinia disease (Sclerotinia sclerotiorum)

Azuki Gray Rust (Bo trytis cin erea)

 Sclerotinia sclerotiorum

Erysiphe graminis f. Sp. Hordei Naked smut, disease (Ustilago n u da)

 Nettle spot (Pyrenophora teres) Black smut (Tille tia con tro versa) Wheat powdery mildew (Erysiphe graminis f. Sp.tritici) Red mold (Gibberella zeae) Red rust (Puccinia recondita)

 Spot disease (Cochliobolus sativus)

 Eye fe: Disease (Pseudocercosporella herp o trich oiaes) Blight (Leptoshaeria nodorum)

 Leaf blight (Septoria tritici)

 Red snow rot (Micron e c trielJa nivalis) Snow rot (Typh ula sp., Micron e c triella nivalis) Strawberry powdery mildew (Sohaerotheca hum uh)

 Gray Rust. (Bo trytis cin ere a)

Charcoal purse (Colletorrich urn gloeosporioides) Table 3 3

 Tomato powdery mildew (Oidium viol a e)

 Gray rust (Botrytis cinerea)

 Leaf mold Fu] via fulva) Tohei (Phytophthora infestans)

 Ring spot \ Altern aria solani)

Grape Udonko (Un cin ula neca tor)

 Gray mold (Botrytis cinerea)

 Downy mildew (Plasmopara viticola)

 Rust (Physopella ampelopsidis) 晚 Rot (Glomerella cingulata)

 Black rot (Elsioe amp e Jin a)

 Lingo powdery mildew (Podosphaera leucotricha)

 , Scab (Ven tulia inaequalis)

 Rot (Valsa cera tosperm a)

 Spot deciduous disease (Alternalia m all)

 Brown spot (Diplocarpon mali)

 Monilinia mali)

 Black spot disease (Mycosph a erella pomi)

Pear (Venturia nashicola)

 Black spot (Alternaria kikuchiana) Scab (Gymn osp orangium a si a ticu) Ring spot (Bo tryosph a eria berengeriana) Oyster powdery mildew (Phyllactinia kakicola)

 Charcoal 3 & Byung (Gloeosporium kaki)

 Circospora kaki KMycosphaerella na wae) Cercospora kaki

Peach ash (Monilinia fructicola)

 Black star ίhei '(Cladosporium carpophilu) Onion Gray mold (Bo trytis cin erea)

 Gray rot (Bo trytis allii)

 Colle to trich um Jin dem u thian um (Pestalotia theae)

Anthrax (Colle to trich um theae 'sin en sis) Reticulum (Exob a sidi um re tic ula t um) Leaf spot (Blsinoe le cospila) Table 3 4

Gray canker, Bo trytis cin ere a)

 Scab (Elsinoe fa wcettii)

 Blue mold (Penicillium i tali cum) Green mold (Penicillium digitatum) Black spot (Diaporthe citn)

Rice blast (Pyricularia oryzae)

 Rhizoctonia solani)

 Idiot disease (Gibberella fujik uroi) sesame leaf blight (Cochliobolus miyabean us) octopus powdery mildew (Erysiphe cichoracearum) sclerotium disease (Sclerotinia sclerotioruni) plague (Phytoph th ora nico tian ae) red scab (Alternaria longipes)

 Charcoal purse (CoUectotrich um tabacum) Tulip gray rot (Bo trytis cin ere a) Rose powdery mildew (Sphaerotheca pannosa)

 (Diplocarpon rosae)

Chrysanthemum brown spot (Sep toria ch rysan themi -in dici) white rust (Puccini a horiana)

Soybean purpura (Cercospora kikuchii) Potato blight (Phytophthora infestans)

 (Alternaria solani)

Sugar beet Brown spot (Cercospora beticola) Laccasei Brown spot (Mycosph a erella arachidis) Black spot (Mycosph a erella berkeleyi)

When the compound according to the present invention is used as a component of an agricultural and horticultural fungicide, the compound according to the present invention can be formulated into a conventional formulation and used. That is, the compound according to the present invention and a suitable carrier and auxiliary agent, for example, a surfactant, a binder, a stabilizer and the like can be blended to prepare a formulation generally used as a formulation of an agricultural chemical. That is, the compound of the general formula (1) according to the present invention includes, for example, powder, coarse powder, DL (driftless type) powder, flodstat, fine granule, fine granule, granule, tablet, and wettable powder. It can be formulated into hydrated granules, sols (flowables), emulsions and oils. The dosage forms that can be prepared are not limited to those listed here.

 As a carrier that can be used for formulation, any carrier that is commonly used for agricultural and horticultural fungicides can be used, and it is not limited to a specific carrier.

 Such solid carriers include, for example, animal and plant powders such as starch, activated carbon, soy flour, flour, wood flour, fish meal, milk powder, talc, kaolin, bentonite, zeolite diatomaceous earth, white carbon, clay, alumina And mineral powders such as calcium carbonate, potassium chloride and ammonium sulfate. .

 Examples of the liquid carrier include water; alcohols such as isopropyl alcohol and ethylene glycol; ketones such as hexahexanone and methylethyl ketone; propylene glycol monomethyl ether, and ethylene glycol mono-n-butyl ether. Ethers; aliphatic hydrocarbons such as kerosene and gas oil; xylene, trimethylbenzene, tetramethylbenzene, methylnaphthine, sorbent and naphtha; aromatic hydrocarbons such as N-methyl-2-pyrrolidone Amides; esters such as glycerin esters of fatty acids; and vegetable oils such as soybean oil and rapeseed oil.

These carriers can be used alone or in combination of two or more. Surfactants that can be used in the formulation include nonionic surfactants, anionic surfactants, cationic surfactants, and amphoteric surfactants. Things can be used.

 Examples of nonionic surfactants include, for example, polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene styryl phenyl ether, polyoxyethylene alkyl ester, polyoxyethylene sorbin alkylate, polyoxyethylene Examples include ethylene phenyl ether polymer, polyoxyethylene alkylene aryl phenyl ether, polyoxyethylene alkylene glycol, and polyoxyethylene polyoxypropylene block polymer.

 Examples of anionic surfactants include, for example, lignin sulfonate, alkylaryl sulfonate, dialkyl sulfosuccinate, polyoxyethylene alkylaryl ether sulfate, alkyl naphthylene sulfonate, polyoxyethylene Styrylphenyl ether sulfate and the like.

 Examples of the cationic surfactant include, for example, an alkylamine salt and the like.

 Examples of the amphoteric surfactant include, for example, quaternary ammonium salt alkylbenzene in, amine oxide and the like.

 The surfactants that can be used in the formulation are not limited to these, and they may be used alone or in combination of two or more.

 Other auxiliary agents include binders, thickeners, fixing agents, preservatives, fungicides, solvents, pesticide active ingredient stabilizers, antioxidants, UV inhibitors, crystal precipitation inhibitors, defoamers, Examples include, but are not limited to, physical property improvers, colorants, and the like, and these auxiliaries can be added as needed.

The binding agent, thickening agent and fixing agent are not particularly limited, For example, starch, dextrin, cellulose, methylcellulose, ethylcellulose, carboxymethylcellulose, hydroxyethylcellulose, hydroxypropylcellulose, hydroxypropylmethylcellulose, carboxymethylstarch, pullulan, sodium alginate, ammonium alginate Propylene glycol alginate, guar gum, 'gum cast bean gum, gum arabic, xanthan gum, gelatin, casein, polyvinyl alcohol, polyethylene oxide, polyethylene glycol, ethylene.Propylene block polymer-sodium polyacrylate And polyvinyl alcohol.

 The amount of the compound of the present invention to be added can be appropriately determined depending on the dosage form of the preparation and the method of use, and it is generally desirable to use the compound in the range of 0.1 to 90% by weight.

 Although the compound according to the present invention is sufficiently effective when used alone, it is used in combination with one or more selected from various fungicides, insecticides and acaricides, and synergists. You can also. Representative examples of fungicides, insecticides, and acaricides that can be used by mixing with the compound of the present invention are shown below. .

(Bactericide) Kyabtan, Holpett, Thiuram, Jiram, Zineb, Manneb, Manzeb, Probineb, Polycarbamate, Kuroguchironil, Quintzen, Capyahor, Iprodione, Procymidone, Fluorimid, Mepronil, Flutranil , Pencyclon, oxycarboxin, Josetyl, triazimefone, triazimenol, propiconazole, diclobutrazol, vitelenol, hexaconazole, microbutenil, flusilazole, metconazole, etaconazole, fluotrimazoline , Cyproconazole, epoxyconazole, flutriafen, benconazole, diniconazole, cyproconazole, fenarimol, triflumizole, prochloraz, imazalil, 、 furazoe Door, door Li Demorufu, fenpropimorph, door Rihorin, pyridinium Hue Knox, § two Razine, polyoxin, metalaxyl, oxadixyl, furalaxyl, isoprothiolane, probenazole, pyrrolnitrin, plastocidin S, kasugamycin, noridamycin, dihydrostrebtomycin sulfate, benomyl, carbendazim, thiophanemethoxide methyl Copper chloride, basic copper sulfate, dietofencalp, metasulfocarb, quinomethionate, pinapacryl, lecithin, baking soda, dithianon, dinocap, phenaminosulf, diclomedine, dozine, IBP, edifenphos, mepanipyrim, pherimison, triclimid, fluazimide , Etokinolac, dimethomorph, pyroquilon, teclophthalam, fusaride, phenazine oxide, thiapendazole, Rishikura tetrazole, cymoxanil, Puropamokarupu hydrochloride, Okisorinidzuku acid, arsenate de Loki Consequences Soki no doubt - le, I Minokutajin triacetate salt, Tetorakonazo Ichiru, Lee Mibenkonazo Ichiru and metiram.

 (Insecticides and miticides) Organophosphorus and carbamate insecticides; phenthione, phennitrothion, diazinon, chlorpyrifos, ESP ヽ bamidothion, fentoate, dimethate, formotione, malazone, trichlorfon, thiomethone, phosmet, Dilorvos, Acephate, EPBP, Methylparathion, Oxidimethone-methyl, Ethion, Salithion, Cyanophos, Isoxathion, Pyridafention, Hosalon, Methidathion, Sulprofos, Chlorfenvinphos, Tetrachlorbinphos, Dimethylvinphos, Propafos, Propaphos, Propaphos , Biraclofos, Monochrome tophos, Azinphos-methyl, Aldicarb, Methomil, Zodicalp, Carbo Orchids, carbosulfan, benfuracarb, Furachiokarupu, propoxycarbonyl sake, B P M (:, M T M C, M I P C, force Rubariru, pyridinium Mikabu, E Chio Fen Culp, Fuenokishikarupu, such as E D D P.

Pyrethroid insecticides; permethrin, cypermethrin, del yus metrine, fenvalerate, fenpronotrin, pyrethrin, arelesli , Tetramethrin, resmethrin, dimethrin, propasulin, phenothrin, protrin, fluparinate, cyfluthrin, cyhalothrin, flucitrinet, etofenprox, cycloprotrin, tralomethrin, silafluophan, brofenprox , Acrinasulin and the like. Benzoylpereas and other insecticides; difluvenzuron, chlorfluazuron, hexaflumuron, triflumuron, tetrabenzuron, flufenoxuron, flucycloxuron, puprofezin, pyriproxyfen, methoprene, benzepin, diafenthiuron, acetamimi Pride, imidacloprid, ditenviram, fipronil, cartap, thiocyclam, bensultap., Nicotine sulfate, rotenone, metaaldehyde, machine oil, microbial pesticides such as BT and insect viruses.

 (Nematocide) Fenamiphos, phosthiazetate, etc.

 (Acaricide) Chlorbenzylate, fenisobromolate, dicofol, amitraz, BPPS ヽ benzomate, hexithiaox, fentin oxide, polynactin, quinomethionate, CPCBS, tetradifon, avermectin, milmectin, clos Fuentezin, cyhexatin, pyridapen, fenpyroximate, tebufenvirad, pyrimidifene, phenothocalp, dienochlor, etc.

 A fungicide for agricultural and horticultural use containing the compound represented by the general formula (A), the general formula (B) or the general formula (C) as an active ingredient (hereinafter, also referred to as “a fungicide for agricultural and horticultural use according to the present invention”) The usage of is generally as follows. That is, in the case of wettable powders, solutions, emulsions, sols (flowables), granule wettable powders and oils, the active ingredient is generally diluted 50-1000 times with water. It is adjusted to a concentration of ~ 100 ppm. This diluted solution is applied to the foliage of the site where the disease of the plant occurs in the range of 10 to 2000 liters per 10 ares, usually in the range of 20 to 700 liters.

In the case of liquids, emulsions and sols (floor pulls), they are not diluted with water, but are used as a concentrated solution, or diluted with water within 50 times, mainly for aerial spraying. As a small amount of spraying agents (LV spraying, ULV spraying, S spraying), 50-5000ml per 10 ares is sprayed using a helicopter. In the case of powder, coarse powder, DL powder, flodust, fine granules, fine granules and granules, 2 to 5 kg (about 5 to 500 g as active ingredient) per 10 ares It is applied to foliage at the site of disease, soil surface, in soil or on the water surface. BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples. Examples 1 to 13 (Production Examples) Production methods of compounds represented by general formula (A) (Examples 1 to 4)

 Example 1

 Preparation of 5-methylene 7-methylisobutylamino-6- (2,5-dichro--3-thenyl) 1-1,2,4-triazolo [1,5a] pyrimidine (Compound No. A— 1 1)

In a 50-ml four-necked flask, 5,7-dichloro-6- (2,5-dichloro-1-thienyl) —1,2,4-triazolo [1,5a] Dissolve 2 g (6 mmo 1) of virimidine and add, then add 5 ml of a mouthpiece form solution containing 0.8 g (8 mmo 1) of triethylamine and 0.5 g (6 mmo 1) of methylisobutylamine Then, the mixture was stirred at room temperature for 30 minutes. After completion of the reaction, the reaction mixture was washed twice with water, and then dried over anhydrous sodium sulfate. The residue obtained by evaporating the solvent under reduced pressure was purified by silica gel chromatography (eluent: toluene: acetone-2 20: 1), and the title compound was purified by 5-chloro-7-methyl-ethyl acetate. Soptylamino-6- (2,5-dichro-3--3-enyl) —1,2,4-triazolo [1,5a] pyrimidine 2.1 g (90% yield) was a white crystal (melting point). 16 2 to 16 3 ° C).

MS (M + 3 9 0) : 1 H-NMR (CD C l 3 d 8. 3 5 (s, 1 H); 6. 8 0 (s, 1 H); 3. 2 0 (s, 3 H) ; 3.06 (m, 1H); 2.82 (m, 1H); 1.92 (m, 1H); 0.81 (d, 6H))

 Example 2

 Preparation of 5-chloro-7-methylisobutylamino-6- (2-methyl-5-chloro-4-4-pyrimidyl) 1-1,2,4-triazolo [1,5a] pyrimidine (compound N o A— 6 4)

 In a 50 ml four-necked flask, add 5,7-dichloro-1-6- (2-methyl-5-chloro-4-pyrimidyl) -1,2,4, -triazolo to 20 ml of black-mouthed form. [1,5a] Pyrimidine 1.9 g (6 mmo 1) is dissolved and added, to which 0.8 g (8 mmo 1) of triethylamine and 0.5 g (6 mmo 1) of methyl isobutylamine are added. ) Was dissolved therein, and 5 ml of a chloroform solution was added dropwise thereto, followed by stirring at room temperature for 30 minutes. After the completion of the reaction, the reaction mixture was washed twice with water, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel chromatography (developing solvent; toluene: acetone = 20: 1) to give the title compound 5-chloro-7-methylisobutylamine. 6- (2-Methyl-5-chloro-4-pyrimidyl) 1-1,2,4-triazolo [1,5a] pyrimidine 1.8 g (80% yield) was a white crystal (melting point: 153). 1154 ° C.).

1 H-NMR (CD C 1 3 (8. 7 8 (s, 1 Η);? 8. 3 8 (s, 1 H); 3. 4 6 (m, 1 H) 2. 9 5 (s, 3H); 2.84 (s, m, 4H); 1.93 (m, 1H); 0.85 (m, 6H))

 Example 3

7-Methylisobutylamino-6- (3,5-dimethyl 1-Bilazolyl) 1,2,4-Triazolo [1,5a] Production of Hymidine (Compound N 0. A-99)

 In a 50 ml four-necked flask, 5,7-dichloro-6- (3,5-dimethyl-1-birazolyl) —1,2,4-triazolo [1,5a] 1.7 g (6 mm o 1) of pyrimidine was dissolved and added, and 0.8 g (8 mm o l) of triethylamine and 0.5 g (6 mm o 1) of methyl isobutylamine were dissolved therein. 5 ml of black-mouthed form was added dropwise, followed by stirring at room temperature for 30 minutes. After the completion of the reaction, the reaction mixture was washed twice with water and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel chromatography (developing solvent; toluene: acetone = 20: 1) to give the title compound 5-chloro-7-methylisobutylamino. — 6— (3,5-Dimethyl-1-birazolyl) — 1,2,4-triazolo [1,5a] pyrimidine 1.7 g (84% yield) is a white crystal (mp 136-137 °) C).

MS (M + 1 334): 1 H-NMR (CD C 1 3 (58. 35 (s, 1 H); 6. 05 (s, 1 H); 3. 39 (m, 1 H) 3. 08 (m, 1H); 2.96 (s, 3H); 2.30 (s, 3H) 2.15 (s, 3H) 1.94 (m, 1H); 0, 87 (m , 6 H))

 Example 4

 Preparation of 5-methylthio-1 7-methylisobutylamino-6- (3,5-dimethyl-1-11-pyrazolyl) -1,2,4-triazolo [1,5a] pyrimidine (Compound No. A— 102)

In a 50 ml 1-capacity four-necked flask, add 20 ml of dimethyl sulfoxide to 5-methyl-17-methylisobutylamino-6- (3,5-dimethyl-1-1-pyrazolyl) -1,2,4- 1.7 g (5 mm 01) of triazolo [1,5a] pyrimidine is dissolved and added, and 2.3 g (5 mmo 1) of a 15% aqueous methylmer solution is added dropwise at room temperature. The mixture was stirred for one hour. After the completion of the reaction, add 30 ml of chloroform to the reaction mixture and add water twice. After washing, it was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel chromatography (developing solvent; toluene: acetone == 30: 1) to give the title compound, 5-methylthio-7-methylisobutyla. Minnow 6— (3,5-dimethyl-1-biazolyl) 1-1,2,4-triazolo [1,5a] pyrimidine 1.5 g (85% yield) was a white crystal (melting point 146-148 ° C) ).

MS (M + 345): 1 H-NMR (CD C l 3 d 8. 25 (s, 1 H); 6. 04 (s, 1 H); 3. 19 (m, 1 H) 2. 94 (s , M, 4H); 2.53 (s, 3H); 2.31 (s, 3H) 2.12 (s, 3H) 1.91 (m, 1H); 0.82 (m, 6 H))

Method for producing compound represented by general formula (B) (Examples 5 to 11)

 Example 5

 Production of 7- (4-Methyl-1-piperidyl) 1 6- (2,5-dichloro-1-3-phenyl) 1,2,4-Triazolo [1,5a] pyrimidine ( Compound No. B-19)

 In a 50 ml capacity four-necked flask, 5,7-dichro-6- (2,5-dichro-3-3-chenyl) 1-1,2,4-triazolo in 20 ml of black-mouthed form , 5a] Pyrimidine 2 g (6 mm 01) was dissolved and added, to which 0.8 g (8 mmol) of triethylamine and 0.6 g (6 mm 01) of 4-pipecoline were dissolved 5 ml of black-mouthed form was added dropwise, and the mixture was stirred at room temperature for 30 minutes. After completion of the reaction, the anti-jfe mixture was washed twice with water, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel chromatography (developing solvent; toluene: acetone = 20: 1) to give the title compound 5-chloro-7- (4-methyl-1 —Piperidyl) 1 6— (2,5-dichroic 1-3-chenyl) 1,1,2,4-triazolo [1,5a] pyrimidine 2.3 g (95% yield) is a white crystal ( Melting point 176-178 ° C).

MS (M + 402): 1 H-NMR (CDC 1 3 (58. 35 (s, 1 H); 6.85 (s, 1 H); 4.10 (m, 1 H); 3.54 (m, 1 H); 3.03 (m, 1 H); 2.89 (m, 1 H); 1.74-1.27 (m, 5 H); 0.99 (d, 3 H))

 Example 6

 Production of 5-chloro-1- (4-ethoxycarbonyl-1-piperidyl) -1-6-1 (2,5-dichloro-1-thienyl) 1-1,2,4-triazolo [1,5a] pyrimidine ( Compound No. B—28)

 In a 50-ml four-necked flask, add 5,7-dichroic 1-6— (2,5-dichroic 1-3-chenyl) 1 1,2,4—triazolo [1,5a] 1.7 g (5 mmo1) of pyrimidine are dissolved and added, and 0.65 g (6.5 mmo1) of triethylamine and 0.8 g (5 mmo1) of 4-ethoxycarbonylbiperidine are added thereto. 5 ml of the dissolved form was added dropwise and stirred at room temperature for 1 hour. After the completion of the reaction, the reaction mixture was washed twice with water, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel chromatography (developing solvent; toluene: acetone = 20: 1) to give the title compound 5-chloro-1--7- (4-ethoxycarbonyl). L-pyridine 1-yl) -1-6- (2: 5-dichloro-1-3-enyl) 1,1,2,4-triazolo [1,5a] pyrimidine 2.0 g (87% yield) as white crystals (Melting point: 156 to 157 ° C).

MS (M + 1 46 1) :. 1 H-NMR (CD C 1 3 58. 37 (s, 1 H); 6. 86 (s, 1 H); 4. 1 6 (q, 2 H); 4 0 2 (m, 1 H); 3.55 (m, 1 H); 3.16-3. 03 (m ₃ 2 H); 2.55 (m, 1 H); 2.05- 1.78 (m, 4 H); 1.27 (t, 3 H))

 Example 7

5-Chloro-7— (3,5 dimethyl-1-birazolyl) 1 6— (2,5-dichloro-3-cenyl) 1-1,2,4-1 Triazolo [1,5a] Production of pyrimidine (Compound No. B-38)

 In a 50 ml four-necked flask, dissolve 3.57 g (6 mmo1) of dimethylformamide in 20 ml of dimethylformamide and add under water cooling 60% oily hydrogenated sodium hydroxide. 0.24 g (6 mmo l)

It was added in 15 minutes and stirred for 1 hour at room temperature. Then, 5,7-dichloro-6- (2,5-dichloro-1-thienyl) 1-1,2,4-triazolo

[1, 5a] Pyrimidine (2 g, 6 mmo 1) was added, and the mixture was stirred at room temperature for 3 hours. After the completion of the reaction, the reaction mixture was put into water and extracted with toluene. The toluene layer was washed three times with a saturated saline solution, and then dried with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was subjected to silica gel chromatography.

Purify with (developing solvent; toluene: acetone = 30: 1) to give the title compound 5-chloro-1,7- (3,5-dimethyl-1-pyrazolyl) -1-6- (2,5-dichloro-1-3-enyl) 1.4 g (58% yield) of 1,2,4-triazolo [1,5a] bilimidine was obtained as white crystals (melting point: 193-194 ° C).

MS (M + 399):. 1 H- NMR (CD C 1 3 <58 54 (s, 1 H); 6. 85 (s, 1 H); 6. 0 5 (s, 1 H); 2. 2 1 (s, 3H); 2.17 (s, 3H))

 Example 8

 5-Chloro-7— (4-Methyl-1-biperidyl) 1 6— (2-Methyl 1-5—Chloro-1-pyrimidyl) 1,1,2,4-1 Triazolo [1,5a] Production of bilimidine ( Compound No. B-68)

In a 50-ml four-necked flask, add 5,7-dichloro-6- (2-methyl-1-5-chloro-1-4-pyrimidyl) -1,1,2,4-triazolo to 20 ml of black-mouthed form [1,5] a] Dissolve 1.9 g (6 mmo 1) of bilimidine and add to it 0.8 mL (8 mmo 1) of triethylamine and 0.6 g (6 mmo 1) of 4-pipecoline 5 ml of mouth form was added dropwise, and the mixture was stirred at room temperature for 30 minutes. After the reaction is completed, the reaction mixture is After washing twice, it was dried with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel chromatography (developing solvent; toluene: acetone = 30: 1) to give the title compound 5-chloro- 7- (4-methyl-1-) Piperidyl) 1 6— (2-Methyl-5-chloro-1-41-pyrimidyl) — 1,2,4-Triazolo [1,5a] pyrimidine 2 g (88% yield) is a white crystal ( Melting point 200-201 ° C).

MS (M + 1 378): 1 H-NMR (CD C 1 3 58. 78 (s, 1 Η); 8. 39 (s, 1 H); 3. 86 (m, 1 H); 3. 72 ( 2.83-2.70 (m, 5 H); 1.68-1.5 1 (m, 3 H); 1.40-1.23 (m, 2 H); 0 . 96 (d, 3H))

 Embodiment 9.

 5-—Mouth—7— (4-Methyl-1-piperidyl) — 6— (3,5-Dimethyl-1-birazolyl) -1,2,4-triazolo [1,5a] Preparation of pyrimidine ( Compound No.B-127)

In a 50 ml four-necked flask, 5,7-dichloro-16- (3,5-dimethyl-1-pyrazolyl) -1,2,4— .triazolo [1,5a] 1.7 g (6 mmo 1) of pyrimidine is dissolved and added, to which 0.8 g (8 mmo l) of triethylamine and 0.6 g (6 mm o 1) of 41 pipecoline are dissolved. 5 ml of mouth form was dropped, and the mixture was stirred at room temperature for 30 minutes. After the completion of the reaction, the reaction mixture was washed twice with water and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel chromatography (developing solvent: toluene: acetone = 30: 1) to give the title compound 5-chloro-1- (4 —Methyl-1-piperidyl) — 6— (3,5-Dimethyl-1-pyrazolyl) — 1, -2 ₃ 4—Triazolo [1,5'a] birimidine 1.9 g (Yield 92) %) Were obtained as white crystals (melting point: 138-140 ° C).

MS (M + 345): 1 H-NMR (CD C 1 3 ^ 8. 37 (s, 1 H); 6. 0 5 (s, 1 H); 4. 0 1 (m, 1 H); 3. 84 (m, 1 2003/009615

72

H); 2.92-2.74 (m, 2H); 2.31 (s, 3H); 2.13 (s, 3H); 1.71-1.55 ( m, 3H); 1.40—1.26 (m, 2H); 0.96 (d, 3H))

 Example 10

 5—Methoxy 7— (4-Methyl-11-piperidyl) 1—6— (2,5 Dichloro-mouth 3-Cenyl) 1-1,2,4-Triazolo [1,5a] Production (Compound No. B—34)

 In a 50 ml 1-capacity four-necked flask, add 10 ml of tetrahydrofuran to 10 ml of 5-chloro-7- (4-methyl-1-biperidyl) -1 6- (2,5-dichloro-1-3-enyl) 1-1,2 , 4-Triazolo [1,5a] pyrimidine 1 g (2.5 mmo 1) dissolved and added, 28% sodium methoxide methanol solution 0.5 g (2.5 mmo 1) Was added dropwise, and the mixture was stirred at room temperature for 1 hour. After the completion of the reaction, the reaction mixture was put into water and extracted with toluene. The toluene layer was washed three times with a saturated saline solution, and then dried with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel chromatography (developing solvent; toluene: acetone = 20: 1) to give the title compound 5-methoxy-7- (4-methyl — 1-piperidyl) — 6— (2: 5-dichloro-1-thienyl) -1-1,2,4-triazolo [1,5a] bilimidine 0.85 g (yield 85%) as white crystals (Melting point 201-203 ° C.).

MS (M + 1 3 9 8 ): 1 H -NMR (CDC 1 3 (5 8. 2 6 (s, 1 H); 6. 7 8 (s, 1 H); 4. 0 4 (m, 4 H) 3.40 (m, 1 H); 3.04 (m, 1 H); 2.85 (m, 1 H); 1.72-1.22 (m, 5 H) ; 0.98 (d, 3 H))

 Example 11

5-Methylthio-1 7- (4-Methyl-1-piperidyl) 1.6- (3,5-Dimethyl-1-pyrazolyl) 1-1,2,4-Triazolo [1,5a] pyrimidine production ( Compound N 0. B— 1 3 0) In a 50 ml four-necked flask, 20-ml of dimethylsulfoxide was charged with 5-chloro-7- (4-methyl-1-piperidyl) -1 6- (3,5-dimethyl-1-1-pyrazolyl) 1-1, 2,4— Triazolo [1,5a] pyrimidine 1.2 g (3.5 mmo 1) dissolved and added, 15 g methyl mercaptan sodium aqueous solution 1.6 g (3.5 mm ol) Was added dropwise and stirred at room temperature for 1 hour. After the completion of the reaction, the reaction mixture was added with chloroform and washed twice with water, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel chromatography (developing solvent; toluene: acetone = 30: 1) to give the title compound 5-methylthio-7- (4-methyl). — 1—Biperidyl) 1 6— (3,5-Dimethyl 1—pyrazolyl) 1-1,2,4-Triazolo [1,5a] pyrimidine 1.0 g (yield 81) was obtained as a white crystal ( Melting point 158-: 159 ° C).

MS (M + 3 5 8) : 1 H-NMR (CD C 1 3 5 8. 2 7 (s, 1 H); 6. 0 4 (s, IE); 3. 9 0 - 3. 7 8 (m 2.80—2.67 (m, 2H); 2.53 (s, 3H); 2.32 (s, 3H); 2.10 (s, 3 H); 1.66-1.26 (m, 5 H); 0.95 (d, 3 H))

Method for producing compound represented by general formula (C) (Examples 12 to 13)

 Example 1 2

 Preparation of 5-cyclohexyl 7-cyclohexyl-6- (3,5-dimethyl-11-birazolyl) -1,2,4-triazolo [1,5a] pyrimidine (compound N .. C— 1)

In a 50-ml four-necked flask, add 20 ml of tetrahydrofuran to 5,7-dichloro-1-6- (3,5-dimethyl-11-birazolyl) -1,2,4—triazolo [1, 5 a] pyrimidine 1. those that have been dissolved 7 g (6 mmo l) and chloride Bisujifue two Rufosufui Nopuropiruparaji © beam _{[P d C l 2 (dppp} )] 3 5 mg of (0. 0 6 mmo l) In addition, it was heated to 60 ° C. To this, 6 ml (6 mmol) of an 18% tetrahydrofuran solution of cyclohexylmagnesium bromide was added dropwise over 1 minute, and the mixture was stirred at 60 ° C for 1 hour.

 After the completion of the reaction, the reaction mixture was put into water and extracted with toluene. The toluene layer was washed twice with a saturated saline solution and then dried over anhydrous sodium sulfate. The organic solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel chromatography (eluent; hexane: acetone = 10: 1) to give the title compound 5-chloro-17-cyclohexane. Hexyl-6- (3,5-dimethyl-1-pyrazolyl) -1,2,4-triazolo [1,5a] birimidine 0 · 8 g

(40% yield) was obtained as white crystals (mp mp 204-205 ° C).

 MS (M + 3 3 0)

 Example 1 3

 7-Benzyl-1-6- (3,5-dimethyl-11-birazolyl) — 1,2,4-Triazolo [1,5a] Preparation of pyrimidine (Compound N 0.C— 1 1)

In a 4 ml flask with a volume of 5 ◦ ml, add 2,5 ml of tetrahydrofuran to 5,7-dichloro-6- (3,5-dimethyl-1-pyrazolyl) -1,2,4-triazolo [1,5a ] pyrimidine 1. 7 g (6 mm o 1 ) those that have been dissolve and chloride Bisujifue two Gandolfo staple Ino propyl para Jiu arm _{[P d C l 2 (dppp} )] 3 5 mg (0. 0 6 mmo l) pressurized And warmed to 60 ° C. To this, 6 ml (6 mmo 1) of a 1% benzylmagnesium chloride solution in tetrahydrofuran was added dropwise over 3 minutes, and the mixture was stirred at 60 ° C. for 1 hour.

After completion of the reaction, the reaction mixture was put into water and extracted with toluene. The toluene layer was washed twice with a saturated saline solution and then dried over anhydrous sodium sulfate. The organic solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel chromatography (developing solvent; hexane: carboxylic acid = 10: 1) to give the title compound. Compound 5-Chloroarcyclohexyl-6- (3,5-dimethyl-1-birazolyl) 1-1,2,4-triazolo [1,5a] pyrimidine 0.8 g (40% yield) ) Was obtained as white crystals (mp 60-61 ° C).

 M S (M + 3 3 8) Reference Production Example Method for producing compound represented by general formula (1) (Reference Production Examples 1 to 3)

 Preparation of 5,7-dichloro-1-6- (2,5-dichloro-3-phenyl) 1-1,2,4-triazolo [1,5a] pyrimidine (Compound No. 3)

(1) Synthesis of tert-Chenylmalonic acid getyl ester

 In a 500 ml four-necked flask, add 300 g (0.21 m 01) of 3-thenylacetic acid and 50 g (0.4 g) of diethyl carbonate to 300 ml of dimethylformamide. 2 mol) was dissolved and added, and 8.5 g (0.21 mol) of sodium hydrogen hydride in 60% was added thereto all at once, followed by stirring at room temperature for 4 hours. After the completion of the reaction, the reaction mixture was put into water and extracted with toluene. The toluene layer was washed three times with a saturated saline solution, and then dried with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel chromatography (developing solvent; hexane: acetone 20: 1) to give 3-ethyl cetylmalonate 47 (yield). 92%) was obtained as a yellow oil.

 M S (M + 1 2 4 3)

 (2) Synthesis of 5,7-dihydroxy-6- (3-chenyl) 1-1,2,4-triazolo [1,5a] pyrimidine

Powder in 50 ml 100-ml 4-neck flask with 100 ml capacity Sodium sodium ethoxide 2.8 g (41 mmo 1), 3-amino-1,2,4-triazole 4 g (41 mmo 1) and 10 g of thienylmalonic acid getyl ester 10 g (41 mmo) 1) was added, and the mixture was stirred under reflux for 6 hours. After the completion of the reaction, the mixture was cooled to room temperature, and the precipitated crystals were collected by filtration. 10% hydrochloric acid was added to the crystals obtained as sodium salt, and the precipitated white crystals were collected by filtration and dried to give 5,7-dihydroxy-6- (3-phenyl) 1-1,2,4-. 7 g (73% yield) of triazolo [1,5a] pyrimidine were obtained.

 MS (M + 234)

 (3) Synthesis of 5,7-dichloro-6- (3-cenyl) 1-1,2,4-triazolo [1,5a] pyrimidine (Compound No. 2)

 In a 50 ml four-necked flask, 7 g (3 Ommo 1) of 5,7-dihydroxy-1 6- (3-chanyl) -11,2,4-triazolo [1,5a] pyrimidine and oxy 3 Oml of phosphorus chloride was added, and the mixture was stirred for 3 hours while heating under reflux. After completion of the reaction, phosphorus oxychloride was distilled off under reduced pressure. Toluene was added to the obtained residue for extraction, and the toluene layer was washed three times with a saturated saline solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel chromatography (developing solvent; toluene: aceton = 20: 1) to give 5,7-dichloro-6- (3-phenyl) -one. 6.6 g (80% yield) of 1,2,4-triazolo [1,5a] pyrimidine was obtained as white crystals.

MS (M + 270): 1 H-NMR (. CDC 1 3 <58 56 (s, 1 H); 7. 54 (m, 2 H); 7. 1 8 (m, 1 H))

 (4) Synthesis of 5,7-dichloro-1-6- (2,5-dichloro-3-enyl)-1,2,4-triazolo [1,5a] pyrimidine

10 Om 1-volume four-necked flask, 10 ml of black-mouthed form, 40 ml of carbon tetrachloride, 5,7-dichloro-6- (3-chenyl) 1-1,2,4-triazolo [1,5a ] Add 6 g (22 mm 01) of pyrimidine, 9 g (66 mmo 1) of sulfuryl chloride and a catalytic amount of pyridine, and heat. The mixture was stirred under reflux for 4 hours. After completion of the reaction, the reaction layer was washed once with a saturated saline solution and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was washed with isopropyl ether to give the title compound 5,7-dichrochloride-6- (2,5-dichro-13-chenyl) -11,2,4- Triazolo [1,5a] bilimidine 7 g (93% yield) was obtained as white crystals (melting point 165-170 ° C).

MS (M + 1 341): 1 H -NMR (CD C 1 3 58. 60 (s, 1 H); 6. 84 (s, 1 H))

 Reference Manufacturing ί Row 2

 Preparation of 5,7-dichloro-6- (2-methyl-5-chloro-1-4-birimidyl) 1-1,2,4-triazolo [1,5a] pyrimidine (Compound No. 9)

 (1) Synthesis of getyl ester 2-methyl-1-5-chloro-4-pyrimidylmalonate

 100 ml of dimethylformamide was placed in a 300 ml four-neck flask, and 3 g (69 mmo 1) of 60% oily sodium hydride was added thereto. Under water cooling, 11 g (69 mmo 1) of getyl macrate was added dropwise over 10 minutes. After the addition, the mixture was stirred at room temperature for 20 minutes except for cooling. Next, 4,5-dichloro-1-methylpyrimidine llg (69 mmo 1) was added over 30 minutes, and the mixture was stirred at room temperature for 15 hours. After completion of the reaction, the reaction mixture was put into water and extracted with toluene. The toluene layer was washed three times with a saturated saline solution and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel chromatography (developing solvent; hexane: ethyl acetate = 5: 1) to give 2-methyl-5-chloro-14-4-pyrimidylmalone. 16 g (yield 81%) of the acid getyl ester was obtained as a yellow oil.

 • MS (M + 1 287)

(2) 5, 7-dichloro-1-6- (2-methyl-1-5-chloro-1-4-pyrimid Jill) Synthesis of 1,2,4-triazolo [1,5a] pyrimidine 2-Methyl-5-chloro-4-pyrimidylmalone in a 50-m1-capacity four-necked flask equipped with a Leanschiff tube Acid getyl ester 6 g

(20 mm o 1), 1.8 g (20 mm o 1) of 3-amino-1,2,4-triazole and 5.8 g (40 mm o 1) of tri-n-propylamine were added. The mixture was stirred at 140 ° C. for 5 hours while distilling off ethanol produced during the reaction. After completion of the reaction, the temperature was lowered to room temperature, and the inside of the reaction layer was washed three times with hexane. To this, 21 g (140 mmo 1) of phosphorus oxychloride was added, and the mixture was further stirred under reflux with heating for 3 hours. After completion of the reaction, phosphorus oxychloride was distilled off under reduced pressure. Toluene and water were added to the obtained residue, and the water tank was neutralized with sodium carbonate, followed by small luene extraction. The toluene layer was washed twice with a saturated saline solution, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel chromatography (developing solvent; toluene: acetone = 30: 1) to give the title compound 5,7-dichloromethane—

(2-Methyl-5-chloro-1-4-pyrimidyl) — 1,2,4-Triazo [1,5a] pyrimidine 2.5 g (40% yield) is a yellow crystal (melting point 165) ~ 169 ° C).

MS (M + 3 1 5) : 1 H- NMR (CD C 1 3 (58. 88 (s, 1 H); 8. 64 (s, 1 H); 2. 83 (s, 3 H))

 Reference Example 3

 Preparation of 5,7-dichloro-6- (3,5-dimethyl-1-pyrazolyl) -1, 2,4-triazolo [1,5a] pyrimidine (Compound N 0.6) (1) 3,5 Of dimethyl-dimethyl-1-birazolylmalonate

In a 50-Oml four-necked flask, dissolve 15 g (0.16 mo1) of 3,5-dimethylbiazole in 200 ml of tetrahydrofuran and add under water cooling 60% sodium hydride in oil. 6. 3 g (0.16mo1) was added over 15 minutes and stirred for 1 hour at room temperature. Then, 38 g (0.16 mol) of bromomalonic acid getyl ester was added dropwise over 10 minutes. Left for one day. After completion of the reaction, the reaction mixture was put into water, extracted with toluene, and the toluene-tetrahydrofuran mixed organic layer was washed twice with a saturated saline solution and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel chromatography (developing solvent; toluene: acetone = 20: 1), and 23 g of 3,5-dimethyl-1-ethylpyrazolylmalonate was obtained. (58% yield) was obtained as a pale yellow oil.

 MS (M + 254)

 (2) Synthesis of 5,7-dichloro-6- (3,5-dimethyl-11-pyrazolyl) -1,1,2,4-triazolo [1,5a] pyrimidine

 In a 10 Oml four-necked flask equipped with a lean stack tube, add 23 g (91 mm o 1) of 3-5-dimethyl-1-pyrazolylmalonic acid dimethyl ester to 3-amino-1,2,4- Add 7.6 g (91 mmo 1) of triazole and 26 g (182 mmo 1) of tri-n-propylamine, and remove the Et0H generated during the reaction by distillation at 140 ° C for 5 hours. Stirred. After completion of the reaction, the temperature was lowered to room temperature, and the inside of the reaction layer was washed three times with hexane. To this, 70 g (453 mmo 1) of phosphorus oxychloride was added, and the mixture was further stirred under heating and reflux for 3 hours. After completion of the reaction, phosphorus oxychloride was distilled off under reduced pressure. Toluene and water were added to the obtained residue, and the water tank was neutralized with sodium carbonate and extracted with toluene. The toluene layer was washed twice with a saturated saline solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel chromatography (developing solvent; toluene: acetone = 20: 1) to give the title compound 5,7-dichloro-6- ( 3,5-Dimethyl-1-biazolyl) 1,2,4-triazolo [1,5a] pyrimidine 12 g (yield 45%) was obtained as yellow crystals (melting point 156-160 ° C). Was done.

MS (M + 282): 1 H-NMR (CD C 1 3 58. 64 (s, 1 H); 6. 1 3 (s, 1 H); 2. 33 (s, 3 H); 2. 17 ( s, 3H)) Examples 14 to 28 (Formulation Examples) Formulation examples of formulating the compound (compound represented by the general formula (A), (B) or (C)) according to the present invention as an agricultural / horticultural fungicide (Examples 14 to 28) are described below. Dust (Examples 14 to 16)

 Example 14

 Compound 2 of compound No. A-11, 1 part of PAP (physical property improver) and 97 parts of clay are uniformly ground and mixed to give a dust containing 2% of active ingredient.

 Powders can be obtained in the same manner by using the compounds shown in Tables 1 to 10 in place of the compound No. A-11.

 Example 15

 Uniformly pulverize and mix 2 parts of compound No. B-19, 1 part of PAP (physical property improver) and 97 parts of clay to obtain a powder containing 2% of active ingredient.

 Powders can be obtained in the same manner by using the compounds shown in Tables 11 to 22 in place of the compound No. B-19.

 Example 16

 Uniformly pulverize and mix 2 parts of compound No. C-11, 1 part of PAP (physical property improver) and 97 parts of clay to obtain a powder containing 2% of active ingredient.

 Powders can be obtained in the same manner by using the compounds shown in Tables 23 to 25 in place of the compound N0.C-11.

Wettable powder (Example 17 ~! ■ 9)

Example 17 0961S

81 Compound No. A—A compound of compound A-64, 20 parts of potassium alkylbenzenesulfonate, 3 parts of polyoxyethylene nonylphenyl ether and 5 parts of clay are uniformly mixed and pulverized to obtain an active ingredient of 20 parts. % Wettable powder is obtained.

 A wettable powder can be obtained in the same manner by using the compounds shown in Tables 1 to 10 in place of the compound N0.A-64.

 Example 18

 20 parts of compound No. B-127, 3 parts of potassium alkylbenzenesulfonate, 5 parts of polyoxyethylene nonylphenyl ether and 72 parts of clay are uniformly mixed and pulverized to obtain an active ingredient. A wettable powder containing 20% is obtained.

 A wettable powder can be obtained in the same manner by using the compounds described in Tables 11 to 22 in place of the compound No. B-1_2_7.

 Example 19

 20 parts of compound No. C-1 compound, 3 parts of potassium alkylbenzenesulfonate, 5 parts of polyoxyethylene nonylphenyl ether and 0.72 parts of clay are uniformly mixed and ground to reduce the active ingredient content to 20%. To obtain a wettable powder containing.

 A wettable powder can be obtained in the same manner by using the compounds shown in Tables 23 to 25 in place of the compound No. C-1.

Emulsion (Examples 20 to 22)

 Example 20

 A compound containing 30% of the active ingredient can be dissolved by mixing and dissolving 30 parts of compound No. A—11, 40 parts of methylethyl ketone and 30 parts of polyoxyethylene nonylphenyl ether. obtain.

 Emulsions can be obtained in the same manner by using the compounds shown in Tables 1 to 10 in place of the compound No. A-11.

Example-2 1_ When 30 parts of compound No. B-68, 40 parts of methylethyl ketone and 30 parts of polyoxyethylene nonylphenyl ether are mixed and dissolved, an emulsion containing 30% of the active ingredient is obtained.

 Emulsions can be obtained in the same manner by using the compounds shown in Tables 11 to 22 in place of the compound N0.B-68.

 Example 22

 Emulsion containing 30% of active ingredient by mixing and dissolving 30 parts of compound No.C-1 of compound 1, 40 parts of methyl ethyl ketone and 30 parts of polyoxyethylene nonylphenyl ether Get.

 Emulsions can be obtained in the same manner by using the compounds shown in Tables 23 to 25 in place of the compound No. C-1.

Sol agent (Examples 23 to 25)

 Example 2 3

 Compound No. A—99 parts of compound A-99, 2 parts of lauryl sulfate, 2 parts of sodium alkylnaphthylene sulfonate, 1 part of acetopropyl propyl cellulose and 55 parts of water are uniformly mixed and active. A sol containing 40% of the components is obtained.

 A sol can be obtained in the same manner by using the compounds described in Tables 1 to 10 in place of the compound N 0 .A-99.

 Example 24

 Compound N 0.B-127 parts of compound 127, 2 parts of lauryl sulfate, 2 parts of alkyl naphthylene sodium sulfonate, 1 part of acetopropyl propyl cell mouth and 55 parts of water were uniformly mixed. A sol containing 40% of the active ingredient is obtained.

 A sol can be obtained in the same manner by using the compounds described in Tables 11 to 22 in place of the compound No. B-127.

 Example 2 5

40 parts of compound No. C—11, 2 parts of lauryl sallaet, A mixture of 2 parts of sodium alkylnaphthylene sulfonic acid, 1 part of acetopropylpropyl cellulose and 55 parts of water is uniformly mixed to obtain a sol containing 40% of the active ingredient.

 A sol can be obtained in the same manner by using the compounds shown in Tables 23 to 25 in place of the compound No. C-11.

Granules (Examples 26 to 28)

 Example 26

 Compound No. A-64 (10 parts), lauryl sulfate (1 part), calcium ligninsulfonate (5 parts), bentonite (30 parts) and water (54 parts) were added to water (15 parts), kneaded with a kneader, and then granulated. And granulate with a fluidized drier to obtain granules containing 10% of active ingredient.

 Granules can be obtained in the same manner by using the compounds shown in Tables 1 to 10 in place of the compound No. A-64.

 Example 27

 After adding 15 parts of water to 10 parts of the compound of compound No. B-68, 1 part of lauryl sulfate, 5 parts of calcium ligninsulfonate, 30 parts of bentonite and 54 parts of clay, kneading was carried out using a kneader. Granulate with a granulator and dry with a fluidized drier to obtain granules containing 10% of active ingredient.

 Granules can be obtained in the same manner by using the compounds shown in Tables 11 to 22 in place of the compound οο.Β-68.

 Example 28

 Add 15 parts of water to 10 parts of compound No. C-1 compound, 1 part of lauryl sulfate, 5 parts of calcium ligninsulfonate, 30 parts of bentonite and 54 parts of clay, knead with a kneader, and granulate. Granulate with a mechanical dryer and dry with a fluid dryer to obtain granules containing 10% of active ingredient.

Granules can be obtained in the same manner by using the compounds described in Tables 23 to 25 in place of the compound N0.C-1. Test Examples Specific examples of the usefulness of the compound according to the present invention as an active ingredient of the agricultural and horticultural fungicide and the usefulness of the agricultural and horticultural fungicide according to the present invention are shown in Test Examples 1 to 17. Rice Blast Prevention Effect Test (Test Examples 1-3)

 Test example 1

 A three-leaf stage seedling of rice (cultivar: Asahi) cultivated in a plastic pot having a diameter of 6 cm in a greenhouse was diluted with a predetermined concentration of a wettable powder prepared according to Example 17 in 1 step. 1 O ml was sprayed per pot. On the day after drug treatment, conidia of Pyr iculariao ryz ae (Pyricularia ryz ae) formed on oatmeal agar medium were inoculated in advance, and the disease was controlled in a 24 ° C climate chamber. . Five days after the inoculation of the fungus, the number of rice blast spots on the three leaves was investigated, and the control value (%) was calculated by the following formula. The control value (%) was converted into an evaluation value according to the following criteria.

 This test was performed on a three-pot system per chemical concentration. In addition, the degree of phytotoxicity to rice was investigated according to the following criteria. The results are shown in Table 35.

 The evaluation value of the control effect and the survey index for the degree of chemical damage are the same in Test Examples 2 to 15 below. . Number of lesions in the spray area

Control value (%)-(1) X100 <

 Evaluation value of control effect Control value

 D C

1: Only 0: None

 Spray chemical concentration Control effect

 Test compound No. ¾

 (ppm) evaluation value

 100 5 0

 A-5 0 100 '4 0

 A-5 2 100 4 0

 A— 7 4 100.

 100 5 0

 A-9.9 100 5 0

 A-1 0 2 100 5 0

 A-1 0 5 100 5 0

 A— 1 1 2-100 5 0

 A-1 1 6 100 5 0

 Comparative drug A 200 1 0

 'No scatter zone 0 (27)

Note 1) The values in parentheses in the non-spray plot indicate the average number of rice blast lesions per leaf. Note 2) Comparative drug A is the following comparative drug A, which was prepared and used in place of the compound of the present invention. The same applies to the following table.

Comparative drug A is a compound represented by the following formula, and is a compound described in US Pat. No. 5,593,996. .

 Comparative drug A

Test example 2

 The control value of the wettable powder prepared according to Example 18 was calculated in the same manner as in Test Example 1, and the control value was converted to an evaluation value according to the same standard. In addition, phytotoxicity to paddy rice was investigated according to the same criteria as in Test Example 1. The results are shown in Table 36.

 Table 3 6 Test compound No. Spraying chemical concentration Control effect

 Harm

(ρρπι) evaluation value

 B- 57 100 5 0

 B-62 100 4 0.

B- 93100 4 0

 B-.1 27 100 4 0

 ., Comparative agent B 200 1 0 No spray area 0 (26)

Note 1) The values in parentheses in the non-spray plot indicate the average number of rice blast spots per leaf. Note 2) Comparative drug Β is the following comparative drug 、 and was prepared and used in the same manner instead of the compound of the present invention. The same applies to the following table.

Comparative drug Β is a compound represented by the following formula, and is a compound described in US Pat. No. 5,593,996.

N eight _Cl

 Comparative drug B

Test example 3

 With respect to the wettable powder prepared according to Example 19, the control value was calculated by the same method as in Test Example 1, and the control value was converted to an evaluation value according to the same standard. In addition, phytotoxicity to paddy rice was investigated according to the same criteria as in Test Example 1. The results are shown in Table 37.

 Table 3 7 Test compound No. Concentration of sprayed chemical solution Control effect

 Evaluation value of chemical damage (ppm)

 C-1 100 5 0

 C- 5】 00 3 0

 C- 6 1005 0.

 C-1 9 100 3 0

C-1 0 100 3 0

 C-1 1 100 3 0 Comparative vegetable c 200 1 0

 . No scatter zone '' 0 (27)

Note 1) The values in parentheses in the non-dispersed plot indicate the average number of rice blast lesions per leaf. Note 2) Comparative drug C is the following Comparative Fiber ijC, which was prepared and used in place of the compound of the present invention. The same applies to the following table. Comparative drug C is a compound represented by the following formula, and is a compound described in International Patent Publication No. WO99 / 41255.

Trimming powdery mildew control effect test (Test Examples 4 to 6)

 Test example 4

 To a single-leaf stage seedling of barley (variety: Azuma Golden) cultivated in a plastic pot having a diameter of 6 cm in a greenhouse, a diluted solution of a predetermined concentration of a wettable powder prepared according to Example 17 was used. 10 m 1 was sprayed per pot. The day after the chemical treatment, conidia of rye sip e gram inis (Elysifer graminis), which had previously been formed on barley leaves, were inoculated, and the disease was controlled in an artificial weather chamber at 20 ° C. Seven days after the inoculation, the percentage (%) of the lesion area of the powdery mildew on the first leaf was investigated, and the control value (%) was calculated by the following formula. Then, it was converted to the evaluation value of the control effect in the same manner as in Test Example 1.

 This test was performed on a three-pot system per chemical concentration. In addition, the degree of phytotoxicity to barley was investigated using the same criteria as in Test Example 1. The results are shown in Table 38. Lesion area percentage of scattered area

Control value (%) = (1) X100 Table 38

 Spray chemical concentration Control effect

Test compound No.

 (ppm) evaluation value

 A- 5 0 100 .4 0

 A- 5 2 100 4 0

 A- 60 100 4 0

 A- 64 100 4 0

 A- 8 4 100 5 0

 A- 9 9 100 5 1

 A- 1 02 100 4 0

 A- 1 05 100 4 0

 A- 1 12 100 4 0

 A- 1 16 100 4 0 Comparative drug A 200 2 0 No spray area 0 (58.7)

Note 1) The values in parentheses in the non-sprayed plot indicate the average lesion area ratio (%) of pheasant powdery mildew per leaf. + Test Example 5

For the wettable powder prepared according to Example 18, the control value was calculated by the same method as in Test Example 4, and the control value was converted to an evaluation value according to the same standard. In addition, phytotoxicity to barley was investigated according to the same criteria as in Test Example 1. The results are shown in Table 39.

Table 3 9

 m

 Test compound D C No. Spraying chemical concentration Control effect

 (ppm) evaluation value, °

B-39 100 4 1

 B- 50 100 5 0

 B- 57 100 .4 0

 B- 61 100 4 0

 B- 62 J u u 4]

 J uu A n u

 B- 68〗 uu λ n u

 B- 76 100 4 0

 B-103] 00 4 0

 B- 115.100 5 0

 B-127 100 5 0

 B-133] 00 4 0

 B- 136 '100 5 0 Specific remedy B ■' 200 2 0 No spray area 0 (54.5)

 Note 1) The numbers in parentheses in the non-sprayed plots indicate the average percentage of leafy mildew on the leafy mildew udon per leaf. Test Example 6,

 With respect to the wettable powder prepared according to Example 19, the control value was calculated in the same manner as in Test Example 4, and the control value was converted to an evaluation value according to the same standard. In addition, phytotoxicity to barley was investigated according to the same criteria as in Test Example 1. Table 40 shows the results.

 Table 4 0 ■ Test compound No. Spray chemical concentration Control effect

 (ppm)

C-1 100 5 0 C-1 5 100 3 0 C-6 100 3 0 C-1 9 100 3 0 C-1 10 100 3 0

Indicates commission (). . Wheat leaf rust control effect test (Test Examples 7 to 9)

 Test example 7

 To a single-leaf seedling of wheat (cultivar: Norin 61) grown in a plastic pot with a diameter of 6 cm in a greenhouse, a predetermined concentration diluted solution of wettable powder prepared according to Example 17 was applied. 1 Oml was sprayed per pot. On the day after the chemical treatment, a summer spore of wheat leaf rust fungus (Puc cini nia reec on d it: Puccinia recondit) previously formed on wheat leaves was inoculated, and the disease was controlled in an artificial weather chamber at 20 ° C. Ten days after the inoculation, the number of lesions on the first leaf was examined, and the control value (%) was calculated by the following formula. Then, in the same manner as in Test Example 1, the evaluation value of the control effect was converted.

 This test was performed on a three-pot system per chemical concentration. The degree of phytotoxicity to wheat was investigated using the same criteria as in Test Example 1. The results are shown in Table 41. Number of lesions in the spray area

Control value (%) 2 (1) X100 No. of lesions in no-spray area

Table 4 1 RA: PΓ Tatsuno Nos

 Test compound No.

 (ρρπι)

 A- 2 1 100 4 n

 U

 '' A- 22 100 4 0

 A- 23 ιο'ο 4 0

A- 49 100 4 0

A- 50 100 5 0

A- 52 100 4 0

A- 57 100 4 0

A- 60 100-. 4 0

A- 64 100 4 0

A-74 100 4 0

A-83 100 4 0

A- 84 100 4 0

A- 9 9. 100 5 0

A- 1 05 100 4 0 A- 1 12 100 4 0 A- 1 16 100 4 .0 A- 1 24 '100 4 0 Comparative drug-agent A 200 2 0 No-spray area 0 (44.2)

Note 1) The value in parentheses in the non-sprayed plot indicates the average number of spots of wheat leaf rust per leaf. Test example 8

With respect to the wettable powder prepared according to Example 1.8, the control value was calculated in the same manner as in Test Example 7, and the control value was converted to an evaluation value according to the same standard. In addition, phytotoxicity to wheat was investigated according to the same criteria as in Test Example 1. Table 42 shows the results. · Table 42

 ffl

 r?-R

 Test compound No.-^. | ~ Tf "/ rt" 'Infectivity (ppm)

 ^ Value of D C

 B— 19 100 4 0

 100 4 0

100 4 0

Β-43 100 4 0

Β-5.0 100 4 0

Β- 57 100 5 0

Β-60 100 4 0

Β- 6 1 100 4 0

• Β-'63 100 4 0

• Β- 64 ion 4 0

Β— 66 1 A o n ri '4 0

Β— 68 4 0

Β- 72】 on • 4 0

Β-76 100 4 0

Β-93 100 4. 0

Β-97.100 4 0

Β- 1 02 100 4 0

Β-103 100- 4 0

Β- 1 15 100 .4 0

Β-1 27 100 4 0

Β-133】 00-4 0

Β-141] 00 4 0

Β- 147 100 4 0

-Comparative drug: Β 200 2 0 No spray area 0 (45.3)

Note 1) numbers in non-sprayed plot of () is, _c indicating the average disease number plaque of wheat rust per leaf

Test example 9

With respect to the wettable powder prepared according to Example 19, the control value was calculated in the same manner as in Test Example 7, and the control value was converted to an evaluation value according to the same standard. In addition, phytotoxicity to wheat was investigated according to the same criteria as in Test Example 1. The results are shown in Table 43. Table 4 3 Spray solution / ^ P ry removal \ v Effect /

 Test compound No.

 (nnm J's review

 P-Cho ll-LLI II word S-

C 1 1 100 5 ', 0

 C- 5 100 4 0

 C-1 6 100 5 0

 C—9 100 3 0

 C—10 100 3 0.

 .C- 1 1 100 4 0

 Comparative cryogen. C ... '200 0 0

 No scatter zone 0 (44.2) ''

 Note 1) The values in parentheses in the non-sprayed plot indicate the average number of spots of wheat leaf rust per leaf. Test for control of cucumber and disease (Test Examples 10 to 12)

 Test example 10

 A diluent of a predetermined concentration of a hydrating agent prepared according to Example 1 in a two-leaf stage seedling of a cucumber (variety: Sagami Hanshiro) cultivated in a plastic pot having a diameter of 6 cm in a greenhouse Was sprayed at a rate of 10 ml per pot. The day after the treatment with the agent, spores of Cucumber blight and a fungus (Pseudoperonos spora cuben s sis: Pseudomonas borax benbensis) previously formed on cucumber leaves were inoculated, and the disease was controlled in an artificial weather chamber at 20 ° C. After inoculation 6, the disease area ratio (%) was investigated, and the control value (%) was calculated by the following formula. Then, it was converted to an evaluation value in the same manner as in Test Example 1. This test was performed on a three-pot system per chemical concentration. In addition, the degree of phytotoxicity to cucumbers was investigated using the same criteria as in Test Example 1. The results are shown in Table 44. '' Lesion area of spray area

 Control value = (1) X100

Lesion area percentage of non-scattered area Table 44

 Spray chemical concentration Control effect

Test compound No.

 (ρρω; evaluation value

 A -49 100 4 0

A-1.1 6 100 4 0 Comparative drug A 200 1 0 No spray area 0 (46.3)

Pillars 1) The values in parentheses in the non-sprayed plot are the average lesion area percentage of cucumber and disease per leaf.

(%). Test example 1 1

 For the wettable powder prepared according to Example 18, the control value was calculated in the same manner as in Test Example 10, and the control value was converted to an evaluation value according to the same standard. In addition, phytotoxicity to Kiyuri 'was investigated using the same criteria as in Test Example 1. The results are shown in Table 45.

 Table 4 5 · Test compound No.

 -Drug damage

(ppm) evaluation value

 B-8 100 5 0

B-1 1 100 4 0

B-1 6 100 5 0

B- 24 100 4 0

B— 28 100 4 0

.B-57 100 5 0

'' B- 61 100 5 0

 B- 63 100.5 0

B- 64 100 5 0

B- 68 100 4 0

B- 76 100 4 0

B— 93 100 4 0

B-1 03】 00 4 0

B— 1 24 100 4 0

B- 127 100 5 0

B-133 100 4 0

B-138 100 4 0

B-147】 00 4 0 Comparative drug B 200 1 0 No-spray area 0 (47.3)

(%) 2003/009615

96 Test Example 1 2

 With respect to the wettable powder prepared according to Example 19, the control value was calculated by the same method as in Test Example 10, and the control value was converted to an evaluation value according to the same standard. In addition, phytotoxicity to cucumbers was investigated according to the same criteria as in Test Example 1. The results are shown in Table 46.

 Table 46 Test compound No. Concentration of applied chemicals Control effect

 φρπι) Evaluation value of chemical damage

 C-1 100 5 0

C-1 5 100 3 0

C-1 6 100 3 0

C-1 9 1.00 3 0

 C-1 10 100 3 0. C-1 1 1 100 3 0

'Comparative silica c 200 1 0 Non-dispersed area .0 (46.3)

Note 1) The figures in parentheses in the non-sprayed plot are the average lesion area percentage of cucumber and disease per leaf.

(%). '' Test for control effect of gray mold on cucumber (Test Examples 13 to 15)

 Test example 1 3 '.

 Water-wetting agent prepared according to Example 17 on 1.5-leaf stage seedlings of Kiyuri (cultivar: Sagami Hanjiro) cultivated in a plastic pot with a diameter of 6 cm in a greenhouse The diluted solution of the predetermined concentration was sprayed at 10 ml per pozzot. On the day after the treatment with the pharmaceutical agent, inoculated with agar-containing agar pieces of B. rystisii ii erea (Botrytis cinerea) previously cultured on a potato decoction medium, and placed in a humidity chamber at 20 ° C. I put it. Four days after the inoculation, the lesion diameter (cm) was measured, and the control value (%) was calculated by the following formula. Then, it was converted to an evaluation value in the same manner as in Test Example 1. .

This test was performed on a three-pot system per chemical concentration. In addition, the degree of phytotoxicity to cucumbers was investigated using the same criteria as in the test examples. The results are shown in Table 47. Five

97

Lesion diameter of the spray area

 Control value (%) (1 X100 Lesion diameter of non-sprayed area Table 47 Test compound No. Spraying drug concentration Concentration control effect

 (ppni) evaluation value

 A- 2 100 5 0

 A- 22 100 4 0

 • A- 50 100 4 0

 A- 52 100 5 0

 A- 64】 00 4 0

 A- 74 100 4 0

 A- 84 100 5 0

 A— 99 100 4 0

 A- 1 1 6 100 5 0

 Comparative drug A 200 2 0

 No scatter zone 0 (6cm)

Note 1) The values in parentheses in the non-sprayed plot indicate the average lesion diameter of cucumber gray mold per leaf. ■ Test Example 14

With respect to the wettable powder prepared according to Example 18, the control value was calculated by the same method as in Test Example 13, and the control value was converted to an evaluation value according to the same standard. In addition, phytotoxicity to cucumbers was investigated according to the same criteria as in Test Example 1. The results are shown in Table 48.

Table 48

 Cloth liquid concentration / ^ control effect

 Test compound No.

 No 1 pr $ mil I iLtB

 ■ R_j _ 1 upper Q i 1 n un u A 'n

 ] no 0 n U

Ώ 1 ΠΠ c

 1 uu u n — 1 1 Π uΠu D n c

 1 u Π

Β— 2 8 u ϋ u

Β-3 2 1 uu c n

 0 u r n

Β— 3 9 1 UU 0

 Β— 4 1 1 UU 4 u

Β-43 1 UU n d u

Β— 57 J UU 4 u

Β— 6 1 i no c

 0 u

A

 Jt3— 0 3 n

B— 6 ¾ 1 UU n

B— 6 8 100 • 5 0

B- 9 3 100 4 0

B- 1 03 100 5 0

B- 1 1 5 100 5 0

B- 1 27 100 4 0

B-1 3 8 100 5 0

Comparative drug B. 200. 2 0 No spray area 0 (6cm)

Note 1) Non-spray 数 値 The value in parentheses in 平均 indicates the average lesion diameter of cucumber gray mold per leaf. Test example 1 5

With respect to the wettable powder prepared according to Example 19, the control value was calculated in the same manner as in Test Example 13, and the control value was converted to an evaluation value according to the same standard. In addition, phytotoxicity to cucumbers was investigated according to the same criteria as in Test Example 1. The results are shown in Table 49. Table 4 9 Concentration of sprayed chemicals Control effect

 • I-Daizo No. ^.

 (ppm) evaluation value

 C-1 100 5 0

 C-5 100 3 0

 C- 6 100 3 0

 C-9 100 3 0

 C 1 10 100 3 0

 C-1 11 100 3 0

 Comparative drug c 200 0 0

 No Scatter Area ·

Note 1) The values in parentheses in the non-sprayed plot indicate the average lesion diameter of cucumber gray mold per leaf.

 Ο

 O Cucumber gray mold control effect test (Therapeutic effect) (Test Example 16 1 7)

 Test example 1 6

 Pre-cultured on potato decoction medium on the first leaf of 1.5-leaf stage seedling of Kiyuri (cultivar: Sagami Hanjiro) cultivated in a plastic pot with a diameter of 6 cm in a greenhouse Agar-containing agar pieces of the cucumber gray mold fungus Botrytisci_ne: rea: Botrytis cinerea) were inoculated and kept in a humidity chamber at 20 C for 1 day. After inoculation 1, 10 ml of a diluted solution of a predetermined concentration of wettable powder prepared according to Example 17 was sprayed per pot. After spraying, they were placed again in a humidity chamber at 20 ° C. Four days after application, the lesion diameter (cm) was measured, and the control value (%) was calculated by the following formula.

 This test was performed on a three-pot system per chemical concentration. The results are shown in Table 50. Lesion diameter of the spray area

Control value (%)-(! X100 No lesion spot diameter Table 50

'' Spray chemical concentration Control value

 Test compound No.

 (ρρηι ノ (¾)

 A-8 4 200 70

 UU 449

 A.— 9 9 200 85

 77

 14

 100 5

 No scatter zone 0 (6cm)

 ά • 1) —Non-cloth · The numbers in parentheses in parentheses indicate the average lesion diameter of cucumber gray mold per leaf. Test example 1 Ί

 The control value of the wettable powder prepared according to Example 18 was calculated in the same manner as in Test Example 16. The results are shown in Table 51.

 Table 5 1 Test compound No. Concentration of applied chemical liquid Control effect

 (ppm) (¾)

 B-1 0 3 200 72

 1 00 38

 B-1 2 7 200 72

 1 00 48

 Comparative drug B 200 1 6

 No scatter zone 0 (5.5 cm)

Note 1) The values in parentheses in the non-sprayed plots are: 1. The average lesion diameter of cucumber gray mold per leaf.

 The composition containing the compound according to the present invention can be used for the above-mentioned important diseases of agricultural crops, especially rice blast, rye powdery mildew, wheat red rust, rye downy mildew and rye gray. Various diseases such as mold can be effectively controlled. Therefore, the compound according to the present invention is useful as an aromatic component of an agricultural and horticultural fungicide.

Claims

 The scope of the claims

-General formula (A)

 '[Where

Het _A represents a 5- or 6-membered ring containing a hetero element, and these 璟 represent a halogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkyl group or May be substituted with a C 2 -C 6 alkoxyalkyl group,

X _A is a halogen atom, Shiano group, C 1 ~ C 6 alkoxy group, C l to C 6 alkylthio group, C. 1 to C 6 alkylsulfinyl group, C 1 through C 6 alkylsulfonyl group, C 1 ~ C 6 alkyl Represents an amino group or a C 1 to C 6 alkoxycarbonyl group, and

 1? ^ ぉ and 1,, are the same or different and are each a C 1 -C 10 alkyl group, a C 2 -C 1 alkenyl group, a C 2 -C 10 alkynyl group or a phenyl group (the alkyl group Alkenyl, alkynyl and phenyl are halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 alkylthio, C1 ~ 'C6 alkoxycarbonyl group and carboxyl group, which may be substituted with one or more groups selected from the group consisting of). ] The triazolopyrimidine derivative represented by these.

2. The Het is a group represented by the following general formula Heteti ₅ .

(Where R ₂ and R ₃ are the same or different and represent a hydrogen atom, a C 1 -C 6 alkyl group, a C 1 -C 6 alkoxy group, a C 1 -C 6 haloalkyl group, or a halogen atom) Represents any group of

X _A represents a halogen atom, and '

R _A and R _A , are the same or different and are each a C 1 C 10 alkyl group, a C 2 -C 10 alkenyl group or a C 2 -C 10 alkynyl group (the alkyl group, the alkenyl group and the alkynyl group) May be substituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 haloalkyl group)

The triazolobirimidine derivative according to claim 1, characterized in that:

3. The H et _A is characterized in that the a H et There H et ₆ or H eti ₂ represented is Ru group, tri § triazolopyrimidine derivative of claim 2.

4. General formula (B) ''

'[Where

Het _B represents a 5- or 6-membered ring containing a hetero element, which is a halogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkyl group or a C2- It may be substituted with a C 6 alkoxyalkyl group,.

X _B is halogen atom, Shiano group, C 1 ~ C 6 alkoxy group, C l ~ C 6 alkylthio group, C. 1 to C 6 alkylsulfinyl group, C 1 through C 6 alkylsulfonyl group, C. 1 to C 6 Arukiruamino A C 1 -C 6 alkoxycarbonyl group; and

R _B is attached at the nitrogen atom, a nitrogen-containing heterocyclic ring which may be substituted. ]

A triazolopyrimidine derivative represented by the formula:

5. The the He t _B is a group represented by the general formula H Etet Interview ₅ below

(Where R ₂ and R ₃ may be the same or different, and represent a hydrogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkyl group or a halogen atom. It indicates one of the groups represented), and wherein X _B represents a halogen atom

The triazolopyrimidine derivative according to claim 4, characterized in that:

6. The triazolopyrimidine derivative according to claim 5, wherein the Het _B is a group represented by the Het ₆ or Het ₂ .

 7. General formula (C)

 (C)

 [Where,

H et _c represents a 5- or 6-membered ring containing a hetero element, and The 5- or 6-membered member is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkyl group and a C2-C6 alkoxyalkyl group. May be substituted by a group

_Xc represents a halogen atom, a cyano group, a C1-C6 alkoxy group or a C1-C6 alkylthio group, and

_Rc is a C1-C10 alkyl group, a C2-C10 alkenyl group, a C2-C10 alkynyl group, a C3-C8 cycloalkyl group, a C4-C10 cycloalkyl. Represents an alkyl group or an aralkyl group, and the benzene ring of the aralkyl group may be substituted with a halogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group or a C1-C6 alkylthio group. . ]

A triazolopyrimidine derivative represented by the formula:

8. The above H Θ t _c is the following general formula Het!

[Wherein R ₂ and R ₃ are the same or different and represent a hydrogen atom, a halogen atom, a C 1 -C 6 alkyl group, a C 1 -C 6 alkoxy group or a C 1 -C 6 haloalkyl group] The triazolopyrimidine derivative according to claim 7, which is a group represented by the formula:

9. A fungicide for agricultural and horticultural use, comprising the triazolobirimidine derivative according to any one of claims 1 to 8 as an active ingredient.