WO2003089433A1 - 5,6-DIPHENYLIMIDAZO[1,2-a]PYRIMIDINE AND BACTERICIDAL COMPOSITION CONTAINING THE SAME - Google Patents

Abstract

An imidazopyrimidine represented by the following formula (1): (1) wherein R1 and R2 each represents halogeno; R4 represents halogeno, etc.; R5 represents halogeno, nitro, etc.; m is an integer of 0 to 4; n is an integer of 0 to 5; and when m is an integer of 2 or larger, then R1's may be the same or different atoms, and when n is an integer of 2 or larger, then R5's may be the same or different atoms or groups. It has excellent bactericidal activity against plant diseases.

Description

 Specification

 5,6-Diphenylimidazo [1,2-a] pyrimidine and bactericidal composition containing it

 The present invention relates to 5,6-diphenylimidazo [1,2-a] pyrimidine and a bactericidal composition containing the same. Background art

 Japanese Patent Application Laid-Open No. 2001_43978 discloses an imidazo [1,2-a] pyrimidine represented by the following formula:

Wherein, χ ₁ ~χ ₅ is a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, a substituted or unsubstituted Ararukiru group, a substituted or unsubstituted Ariru group, a substituted or unsubstituted Ararukiruokishi group, there have represents a substituted or unsubstituted Ariruokishi group, further, X and chi _2, chi ₃ and chi _4, and chi ₄ with an adjacent group selected from chi ₅ are each It may combine to form a substituted or unsubstituted carbocyclic aliphatic ring or a substituted or unsubstituted carbocyclic aromatic ring together with a substituted carbon atom. ],

Is described as being effective as a material for an organic electroluminescent device.

 An object of the present invention is to provide a novel imidazo [1,2-a] pyrimidine having excellent control activity against plant diseases. Disclosure of the invention

As a result of intensive studies, the present inventor has found that the 5,6-diphenylanimi represented by formula (1) The present inventors have found that dazo [1,2-a] pyrimidine has an excellent plant disease controlling effect, and have reached the present invention.

 That is, the present invention provides the following formula (1)

Wherein R ¹ and R ² represent a halogen atom, R ⁴ represents a halogen atom, a CI—C4 alkyl group, a C 1—C4 alkoxy group or a cyano group, and R ⁵ represents a halogen atom, a nitro group, a cyano group. Group, CI-C4 alkyl group, C1-C4 alkoxy group, C1-C4 alkylthio group, C1-C4 haloalkylthio group, C1-C4 haloalkyl group, C1-C4 haloalkoxy group, C1 One represents a C4 acyl group, a C2-C5 alkoxycarbonyl group or a phenyl group, m represents an integer of 0 to 4, and n represents an integer of 0 to 5. When m is an integer of 2 or more, R ¹ may represent the same or different atoms, and when n is an integer of 2 or more, R ⁵ may represent the same or different atoms or groups. Good. ]

And a fungicidal composition containing the compound of the present invention as an active ingredient, and a method for controlling plant diseases by applying the compound of the present invention to plants or soil. In the present invention, specific examples of the substituents represented by RR ² , R ⁴ or R ⁵ are shown below.

Examples of the halogen atom represented by R ¹ and R ² include a fluorine atom and a chlorine atom,

Examples of the halogen atom represented by R ⁴ include a chlorine atom and a bromine atom, and examples of the C 1 -C 4 alkyl group include a methyl group, an ethyl group, a propyl group, and an isopropyl group; Examples of the C 1 -C 4 alkoxy group represented by include a methoxy group, an ethoxy group, a propyloxy group and an isopropyloxy group.

Examples of the halogen atom represented by R ⁵ include a fluorine atom, a chlorine atom and a bromine atom,

Examples of the C 1 -C 4 alkyl group represented by R ⁵ include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, an isobutyl group and a tert-butyl group.

Examples of the C 1 -C 4 alkoxy group represented by R ⁵ include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, and a butoxy group.

Examples of the C 1 -C 4 alkylthio group represented by R ⁵ include a methylthio group, an ethylthio group, a propylthio group, and an isopropylthio group.

Examples of the C 1 -C 4 haloalkylthio group represented by R ⁵ include a trifluoromethylthio group and a 1,1,2,2-tetrafluoroethylthio group,

Examples of the C 1 -C 4 haloalkyl group represented by R ⁵ include a trifluoromethyl group,

The C 1 one C 4 haloalkoxy group represented by R ⁵ for example Torifuruorome butoxy group and 1, 1, 2, 2-tetrafluoropropoxy O b ethoxy group, and

Examples of the CI—C 4 acyl group represented by R ⁵ include a formyl group, an acetyl group and a propionyl group.

The C 2 -C 5 alkoxycarbonyl group represented by R ⁵ includes, for example, a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, an isopropoxycarbonyl group and a butoxycarbonyl group.

In the formula (1), examples of the phenyl group substituted by (R ^ and: ² include 2-fluorophenyl group, 2-chlorophenyl group, 2,3-difluorophenyl group, and 2,3-dichlorophenyl Group, 2,4-difluorophenyl group, 2-chloro-4-fluorophenylinole group, 4-chlorophenyl_2-fluorophenyl group, 2,4-dichlorophenol group, 2,5-diphenylolenophenyl Nore group, 2,5-dichlorophenol group, 2,6-diphenoleno group, 2-chloro-6-phenylolephenyl group, 2,6-chlorophenol group, 2,3, 4-Mono-trifluorophenyl group, 2, 3, 5- Trifluorophenyl group, 2,4,5-trifluorophenyl group, 2,3,6-trifluorophenyl group, 2,4,6-trifluorophenyl group, 2-chloro-4,6-diphneololophenyli Nore group, 4,1-dichloro-2-phenylenolenophenyl group, 2,4-dichloro-6-phenylolenophenylene group, 2,6-dichloro-4-phenylene phenyl group, 2,4, 6 _ trichloro mouth phenyl group, 2,3,4,5-tetrafluoro mouth phenyl group, 2,3,4,6-tetrafluorophenyl group, 2,3,5,6-tetrafluorophenyl group, 2,3, 4,5,6-pentafluorophenyl group and 4-chloro-1,2,3,5,6-tetraphenylolenophenyl group are mentioned. As the phenyl group substituted by (R ⁵ ) _n in the formula (1), Is, for example, phenyl, 4-methylphenyl, 3_methylphenyl, 2-methylphenyl group, 4-ethynolephenyl group, 4-propylphenyl group, 4-isopropylphenyl group, 4-butylphenyl group, 41-sec-butynolephenyl group, 4-isobutylphenyl group, 4-tert-butynolephenyl group 2,3-Dimethylphenol group, 2,4-Dimethylphenyl group, 2,5-Dimethyl / lephenyl group, 3,4-Dimethylphenyl group, 3,5-Dimethylphenyl group, 4- Phenylphenyl group, 4-chlorophenyl group, 3-chlorophenyl group, 2-chlorophenyl group, 4-phenololenophenyl group, 3-fluorophenyl group, 2-fluorophenyl group , 2,3-Dichloro phenyl group, 2,4-Dichloro phenyl group, 2,5-Dichloro phenyl group, 3,4-Dichloro phenyl group, 3,5-Dichlorophenyl group, 2, 3 —Difluorophenyl group, 2 , 4-Difnoleolopheninole group, 2,5-Difnoleolopheninole group, 3,4-Difluoropheninole group, 3,5-Difnoleolopheninole group, 2-Clot mouth_4-Fnoleolofenenole group , 4-tri-fluorenolomethinolephenylinole, 3-tri-phenyleno-methylenophenyl, 2-trifluoromethylphenyl, 3,5-bis (trifluoromethyl) phenyl, 4-Methoxyphenyl group, 3-Methoxyphenyl group, 2-Methoxyphenyl group, 2,3-Dimethoxyphenyl group, 2,4 Dimethoxyphenyl group, 2,5-Dimethoxyphenyl group , 3,4-dimethoxyphenyl, 3,5-dimethoxyphenyl, 2,3,4-trimethoxyphenyl, 3,4,5-trimethoxyphenyl, 4-ethoxyphenyl, 3-ethoxy Enyl group, 2-ethoxy Phenyl group, 4-methylthiazol-off enyl, 3-methylthiazol-off enyl, 2-methylthiopheneyl group, 4-trifluoronoremethoxyphenyl group, 3-trifluoromethoxyphenyl group, 2-triphenylenomethoxyphenyl group, 4-cyanophenyl group, 3-cyanophenyl group, 2-cyanophenyl Group, 4-formino phenyl group, 3-formylphenyl group, 2-formylphenyl group, 4-acetylphenyl group, 3-acetylphenyl group, 2-acetylphenyl group, 4- (methoxycalponinole) phenyl group, 4-1 (Ethoxycarbonyl) phenyl group, 4- (isopropoxycarbonyl) phenyl group and 4-fluoro-3-methylphenyl group. Embodiments of the present compound include, for example, the following compounds.

In the formula (1), an imidazopyrimidine compound in which R ¹ is a fluorine atom or a chlorine atom;

An imidazopyrimidine compound wherein R ¹ is a fluorine atom in the formula (1); an imidazopyrimidine compound wherein R ¹ is a chlorine atom in the formula (1);

An imidazopyrimidine compound in which m is an integer of 0 to 2 in the formula (1); an imidazopyrimidine compound in which m is 0 in the formula (1)

In the formula (1), an imidazopyrimidine compound in which m is 1

In the formula (1), an imidazopyrimidine compound in which m is 2

In the formula (1), m is 0, m is 1, and R ¹ is a halogen atom substituted at the 4- or 6-position, or m is 2, and one R ¹ is An imidazopyrimidine compound which is a halogen atom substituted at the 4-position and another R ¹ is a halogen atom substituted at the 6-position;

In the formula (1), m is 1 or 2, and at least one R ¹ is a halogen atom substituted at the 4- or 6-position; an imidazopyrimidine compound;

In the formula (1), m is 0, or m is 1, and R ¹ is a halogen atom substituted at the 4-position, an imidazopyrimidine compound;

In the formula (1), m is 1 and R ¹ is a halogen atom substituted at the 6-position, or m is 2 and one R ¹ is a halogen atom substituted at the 4-position, and An imidazopyrimidine compound, wherein the other R ¹ is a halogen atom substituted at the 6-position; In the formula (1), m is 1, and R ¹ is a fluorine atom or a chlorine atom substituted at the 6-position, or m is 2 and one R ¹ is substituted at the 4-position. Or a chlorine atom, and another: an imidazopyrimidine compound in which R ¹ is a fluorine atom or a chlorine atom substituted at the 6-position;

An imidazopyrimidine compound of the formula (1), wherein m is 1 and R ¹ is a halogen atom substituted at the 4-position;

In the formula (1), m is 1, and R ¹ is a halogen atom substituted at the 6-position, an imidazopyrimidine compound;

In the formula (1), an imidazopyrimidine compound in which m is 2, one R ¹ is a halogen atom substituted at the 4-position, and another R ¹ is a halogen atom substituted at the 6-position;

In the formula (1), an imidazopyrimidine compound in which m is 2, one R ¹ is a halogen atom substituted at the 3-position, and the other R ¹ is a halogen atom substituted at the 6-position;

In the formula (1), m is 1, and R ¹ is a fluorine atom substituted at the 4-position, an imidazopyrimidine compound;

An imidazo pyrimidine compound represented by the formula (1), wherein m is 1 and R ¹ is a chlorine atom substituted at the 6-position;

In the formula (1), an imidazopyrimidine compound in which m is 2, one R ¹ is a fluorine atom substituted at the 4-position, and another R ¹ is a fluorine atom substituted at the 6-position;

In the formula (1), an imidazopyrimidine compound in which m is 2, one R ¹ is a fluorine atom substituted at the 4-position, and another R ¹ is a chlorine atom substituted at the 6-position In the formula (1), m is 2, one R ¹ is a fluorine atom substituted at the 3-position, and another R ¹ is a chlorine atom substituted at the 6-position. In the formula (1), m is 2, one of R ¹ is a chlorine atom substituted at the 4-position, imidazopyrimidine compound is a chlorine atom of another R ¹ is substituted with 6-position; In the formula (1), an imidazopyrimidine compound in which R ² is a fluorine atom or a chlorine atom;

In the formula (1), an imidazopyrimidine compound in which R ² is a fluorine atom; In the formula (1), an imidazopyrimidine compound in which R ² is a chlorine atom;

In the formula (1), an imidazopyrimidine compound in which ¹ and R ² are each independently a fluorine atom or a chlorine atom;

In the formula (1), an imidazopyrimidine compound in which ¹ and R ² are each independently a fluorine atom or a chlorine atom, and m is an integer of 0 to 2;

In the formula (1), m is 0, m is 1, and R ¹ is a fluorine atom substituted at the 4- or 6-position or a chlorine atom substituted at the 4- or 6-position, or M is 2, one R ¹ is a fluorine atom substituted at the 4-position or a chlorine atom substituted at the 4-position, and another R ¹ is a fluorine atom substituted at the 6-position or substituted at the 6-position Imidazopi limidine compound, wherein R ² is a fluorine atom or a chlorine atom;

In the formula (1), m is 1 or 2, and at least one R ¹ is a fluorine atom substituted at the 4- or 6-position or a chlorine atom substituted at the 4- or 6-position, and R ² is fluorine Imidazopyrimidine compounds which are atoms or chlorine atoms;

In the formula (1), m is 1, and R ¹ is a fluorine atom or a chlorine atom substituted at the 6-position, or m is 2, and one R ¹ is a fluorine atom substituted at the 4-position. Or an imidazopyrimidine in which a chlorine atom substituted in the 4-position, another R ¹ is a fluorine atom substituted in the 6-position or a chlorine atom substituted in the 6-position, and R ² is a fluorine atom or a chlorine atom Compound;

In the formula (1), an imidazopyrimidine compound wherein m is 1, R ¹ is a fluorine atom substituted at the 4-position or a chlorine atom substituted at the 4-position, and R ² is a fluorine atom or a chlorine atom;

In the formula (1), an imidazopyrimidine compound wherein m is 1, R ¹ is a phthalene atom substituted at the 6-position or a chlorine atom substituted at the 6-position, and R ² is a fluorine atom or a chlorine atom;

In the formula (1), m is 2, and one R ¹ is a fluorine atom substituted at the 4-position or Is a chlorine atom substituted at the 4-position, another R ¹ is a fluorine atom substituted at the 6-position or a chlorine atom substituted at the 6-position, and R ² is a fluorine atom or a chlorine atom;

In the formula (1), an imidazopyrimidine compound in which R ¹ and R ² are a fluorine atom;

In the formula (1), an imidazopyrimidine compound in which R ¹ and R ² are a fluorine atom and m is an integer of 0 to 2;

In the formula (1), or m is 0, m is 1,: force R ¹ is a fluorine atom substitution in the 4-position or 6-position, or,, m is 2, one of: ¹ Is a fluorine atom substituted at the 4-position, and another: an imidazopyrimidine compound in which ¹ is a fluorine atom substituted at the 6-position, and further R ² is a fluorine atom;

In the formula (1), an imidazopyrimidine compound in which m is 1 or 2, at least one R ¹ is a fluorine atom substituted at the 4- or 6-position, and R ² is a fluorine atom;

In the formula (1), m is 1 and R ¹ is a fluorine atom substituted at the 6-position, or m is 2 and one R ¹ is a fluorine atom substituted at the 4-position. An imidazopyrimidine compound in which another R ¹ is a fluorine atom substituted at the 6-position, and ² is a fluorine atom;

In the formula (1), an imidazopyrimidine compound in which m is 1, R ¹ is a fluorine atom substituted at the 4-position, and R ² is a fluorine atom;

In the formula (1), m is 1, R ¹ is a fluorine atom substituted at the 6-position, and R ² is a fluorine atom, an imidazopyrimidine compound;

In the formula (1), m is 2, one R ¹ is a fluorine atom substituted at the 4-position, another R ¹ is a fluorine atom substituted at the 6-position, and R ² is a fluorine atom An imidazopyrimidine compound;

In the formula (1), m is 1, R ¹ is a fluorine atom substituted at the 6-position, and R ² is a chlorine atom, an imidazopyrimidine compound;

An imidazopyrimidine compound represented by the formula (1), wherein is a halogen atom or a C 1 -C 4 alkyl group; In the formula (1), an imidazopyrimidine conjugate in which R ⁴ is a halogen atom; in the formula (1), an imidazopyrimidine compound in which R ⁴ is a chlorine atom; in the formula (1), R ⁴ is an alkyl group In the formula (1), an imidazopyrimidine compound in which R ⁴ is a methyl group; in the formula (1): an imidazopyrimidine compound in which R ⁴ is an alkoxy group; in the formula (1), R ⁴ is a methoxy group In the formula (1), an imidazopyrimidine compound in which R ⁴ is a cyano group; In the formula (1), an imidazopyrimidine compound in which R ⁴ is a chlorine atom, a methyl group, a methoxy group, or a cyano group ;

In the formula (1), m is an integer of 0 to 2, and R ⁴ is a halogen atom, an imidazo pyrimidine compound;

In the formula (1), m is 0 or m is 1, and R ¹ is a halogen atom substituted at the 4- or 6-position \ or m is 2, and one R ¹ is An imidazopyrimidine compound in which the halogen atom is substituted at the 4-position, another R ¹ is a halogen atom substituted at the 6-position, and R ^{4 is} a halogen atom;

In the formula (1), im is an imidazopyrimidine in which m is 1 or 2, at least one R ¹ is a haguchigen atom substituted at the 4-position or the 6-position, and R ⁴ is a no-halogen atom. Compound;

In the formula (1), m is 1 and R ¹ is a halogen atom substituted at the 6-position, or m is 2 and one R ¹ is a halogen atom substituted at the 4-position, and An imidazopyrimidine compound in which another R ¹ is a Haguchigen atom substituted at the 6-position and R ^{4 is a} Haguchigen atom;

In the formula (1), m is 1, R ¹ is a halogen atom substituted at the 4-position, and R ⁴ is a halogen atom; an imidazopyrimidine compound;

In the formula (1), m is 1, an imidazopyrimidine compound in which R ¹ is a halogen atom substituted at the 6-position, and R ⁴ is a nitrogen atom;

In the formula (1), m is 2, one R ¹ is a halogen atom substituted at the 4-position, another R ¹ is a halogen atom substituted at the 6-position, and R ⁴ is a nitrogen atom. Certain imidazopyrimidine compounds; In the formula (1), an imidazopyrimidine compound in which R ² is a fluorine atom and R ⁴ is a halogen atom;

In the formula (1), an imidazopyrimidine compound in which R ² is a chlorine atom and R ⁴ is a nodogen atom;

In the formula (1), an imidazopyrimidine compound in which m is 1, R ¹ is a chlorine atom substituted at the 6-position, R ² is a chlorine atom, and R ^{4 is a} halogen atom;

In the formula (1), m is 2, one R ¹ is a halogen atom substituted at the 4-position, another R ¹ is a fluorine atom substituted at the 6-position, and R ² is a fluorine atom. An imidazopyrimidine compound in which R ^{4 is a} halogen atom;

In the formula (1), m is 2, one R ¹ is a halogen atom substituted at the 4-position, another R ¹ is a chlorine atom substituted at the 6-position, and R ² is a chlorine atom. An imidazopyrimidine compound in which R ^{4 is a} halogen atom;

In the formula (1), m is 2, one R ¹ is a halogen atom substituted at the 4-position, another R ¹ is a fluorine atom substituted at the 6-position, and R ² is a chlorine atom. ,: An imidazopyrimidine compound in which ^{4 is a} halogen atom;

In the formula (1), m is 2, one of ¹ is a fluorine atom substituted at the 4-position, another R ¹ is a fluorine atom substituted at the 6-position, and R ² is a fluorine atom. And R ^{4 is a} halogen atom; an imidazopyrimidine compound;

In the formula (1), m is 2, one R ¹ is a chlorine atom substituted at the 4-position, another R ¹ is a chlorine atom substituted at the 6-position, and R ² is a chlorine atom. An imidazopyrimidine compound wherein R ⁴ is a halogen atom;

In the formula (1), R ² is a fluorine atom or a chlorine atom; R ⁴ is a chlorine atom; an imidazopyrimidine compound;

In the formula (1), an imidazopyrimidine compound in which R ² is a fluorine atom and R ⁴ is a chlorine atom;

In the formula (1), an imidazopyrimidine compound in which R ² is a chlorine atom and R ⁴ is a chlorine atom;

In the formula (1), a fluorine atom or a chlorine atom and R ¹ and R. ² are each independently, imidazopyrimidine compounds wherein R ⁴ is a chlorine atom; In the formula (1), R ¹ and R ² are each independently a fluorine atom or a chlorine atom, m is an integer of 0 to 2, and: an imidazopyrimidine compound in which R ⁴ is a chlorine atom;

In the formula (1), m is 0, m is 1, and R ¹ is a fluorine atom substituted at the 4- or 6-position or a chlorine atom substituted at the 4- or 6-position, or M is 2, one R ¹ is a fluorine atom substituted at the 4-position or a chlorine atom substituted at the 4-position, and another R ¹ is a fluorine atom substituted at the 6-position or substituted at the 6-position An imidazopyrimidine compound in which ² is a fluorine atom or a chlorine atom, and R ⁴ is a chlorine atom;

In the formula (1), m is 1 or 2, and at least one R ¹ is a fluorine atom substituted at the 4- or 6-position or a chlorine atom substituted at the 4- or 6-position, and R ² is An imidazo pyrimidine compound in which ⁴ is a chlorine atom;

In the formula (1), m is 1, and R ¹ is a fluorine atom substituted at the 6-position or a chlorine atom substituted at the 6-position, or m is 2, and one of: R ¹ is at the 4-position R ¹ is a fluorine atom substituted at the 6-position or a chlorine atom substituted at the 6-position, and R ² is a fluorine atom or a chlorine atom substituted at the 6-position. An imidazopyrimidine compound wherein R ⁴ is a chlorine atom; in the formula (1), m is 1, R ¹ is a fluorine atom substituted at the 4-position or a chlorine atom substituted at the 4-position, and R ² is a fluorine atom An imidazopyrimidine compound which is an atom or a chlorine atom and R ⁴ is a chlorine atom;

In the formula (1), m is 1, R ¹ is a fluorine atom substituted at the 6-position or a chlorine atom substituted at the 6-position, R ² is a fluorine atom or a chlorine atom, and R ⁴ is a chlorine atom. Certain imidazopyrimidine compounds;

In the formula (1), m is 2, and one of: R ¹ is a fluorine atom substituted at the 4-position or a chlorine atom substituted at the 4-position, and another R ¹ is a fluorine atom substituted at the 6-position. Or an imidazopyrimidine compound which is a chlorine atom substituted at the 6-position, R ² is a fluorine atom or a chlorine atom, and R ⁴ is a chlorine atom;

In the formula (1), R ¹ and R ² are fluorine atoms, and R ⁴ is a chlorine atom. Dazopyrimidine compounds;

In the formula (1), an imidazopyrimidine compound in which R ¹ and R ² are a chlorine atom, and R ⁴ is a chlorine atom;

In the formula (1), an imidazopyrimidine compound in which R ¹ is a chlorine atom, R ² is a fluorine atom, and R ⁴ is a chlorine atom;

In the formula (1), an imidazopyrimidine compound in which R ¹ is a fluorine atom, R ² is a chlorine atom, and R ⁴ is a chlorine atom;

In the formula (1), an imidazopyrimidine compound in which R ¹ and R ² are a fluorine atom, m is an integer of 0 to 2, and R ⁴ is a chlorine atom;

In the formula (1), m is 0 or m is 1 and R ¹ is a fluorine atom substituted at the 4- or 6-position \ or m is 2 and one R ¹ is An imidazopyrimidine compound in which a fluorine atom substituted in the 4-position, another R ¹ is a fluorine atom substituted in the 6-position, R ² is a fluorine atom, and R ⁴ is a chlorine atom; )), Wherein m is 1 or 2, at least one R ¹ is a fluorine atom substituted at the 4- or 6-position, R ² is a fluorine atom, and R ⁴ is a chlorine atom. ;

In the formula (1), a force wherein m is 1 and R ¹ is a fluorine atom substituted at the 6-position, or m is 2 and one R ¹ is a fluorine atom substituted at the 4-position. And another R ¹ is a fluorine atom substituted at the 6-position, R ² is a fluorine atom, and an imidazopyrimidine compound in which R ⁴ is a chlorine atom;

In the formula (1), m is 1, R ¹ is a fluorine atom substituted at the 4-position, R ² is a fluorine atom, and R ⁴ is a chlorine atom; an imidazopyrimidine compound; an imidazopyrimidine compound in which m is 1, R ¹ is a fluorine atom substituted at the 6-position, R ² is a fluorine atom, and is a chlorine atom; In the formula (1), m is 2; An imidazopyrimidine compound in which R ¹ is a fluorine atom substituted at the 4-position, another R ¹ is a fluorine atom substituted at the 6-position, and ² is a fluorine atom and R ⁴ is a chlorine atom;

In the formula (1), an imidazopyrimidine compound in which m is 1, R ¹ is a fluorine atom substituted at the 6-position, R ² is a chlorine atom, and R ⁴ is a chlorine atom; In the formula (1), an imidazopyrimidine compound in which m is 1, R ¹ is a halogen atom substituted at the 4-position, and R ⁴ is a chlorine atom;

In the formula (1), m is 1, R ¹ is a halogen atom substituted at the 6-position, and R ⁴ is a chlorine atom, an imidazopyrimidine compound;

In the formula (1), m is 2, one R ¹ is a halogen atom substituted at the 4-position, another R ¹ is a halogen atom substituted at the 6-position, and R ⁴ is a chlorine atom. Imidazopyrimidine compounds;

In the formula (1), m is 2, one of: R ¹ is a halogen atom substituted at the 3-position, and another: R ¹ is a halogen atom substituted at the 6-position, and R ⁴ is a chlorine atom. An imidazopyrimidine compound which is

An imidazopyrimidine compound of the formula (1), wherein n is 0;

An imidazopyrimidine compound of the formula (1), wherein n is 1;

An imidazopyrimidine compound in which n is 1 in the formula (1) and the substitution position of R ⁵ is 4-position;

In the formula (1), n is 1, and R ⁵ is an imidazopyrimidine compound;

In the formula (1), n is 1, and R ⁵ is a C 1 -C 4 alkyl group, an imidazopyrimidine compound;

An imidazo pyrimidine compound in which n is 1 in the formula (1) and R ⁵ is a C 1 -C 4 haloalkyl group;

An imidazopyrimidine compound of the formula (1), wherein n is 1 and R ⁵ is a C 1 -C 4 alkoxy group;

In the formula (1), n is 0, 1 or 2, and R ⁵ is a halogen atom, C 1 -C 4 alkyl group, C 1 -C 4 is an imidoalkyl group or a C 1 -C 4 alkoxy group. Zopyrimidine compounds;

An imidazopyrimidine compound represented by the formula (1), wherein n is 1 and R ⁵ is a chlorine atom substituted at the 4-position or a methyl group substituted at the 4-position.

Among the compounds of the present invention, a compound represented by the formula (2) (hereinafter, referred to as compound (2) o)

[Wherein: ¹ R ² , R m and n represent the same meaning as described above, and R ⁴ ° represents a halogen atom or a C 1 -C 4 alkyl group. ]

Is a compound represented by the formula (3) (hereinafter, referred to as compound (3)):

[Wherein, R ¹ R ² , R ⁴ ° and m represent the same meaning as described above, and X ¹ represents a halogen atom (for example, a chlorine atom or the like). ]

And phenylporonic acid represented by the formula (4) (hereinafter, referred to as compound (4))

[Wherein, R ⁵ and n represent the same meaning as described above. ]

And in the presence of a palladium catalyst. The reaction is usually performed in a solvent in the presence of a base. Examples of the solvent used in the reaction include ethers such as methinolate tert-butyl ether, ethylene glycol dimethinole ether, tetrahydrofuran and 1,4-dioxane, and aliphatic hydrocarbons such as hexane, heptane and octane. And aromatic hydrocarbons such as toluene, xylene and the like, nitriles such as acetonitrile and butyronitrile, water and a mixture thereof.

Examples of the palladium catalyst used in the reaction include palladium acetate, tetrakistrifuedinolephosphine palladium, {1,1′-bis (diphen-norephosphino) phenoctene} dioctane palladium (II) methylene chloride complex, bis chloride ( bird Phenylphosphine) palladium, salted-on {1,4-bis (diphenylenophosphinobutane)} palladium and {1,3-bis (diphenylphosphino) propane chloride} palladium. Examples include sodium bicarbonate, potassium bicarbonate, sodium carbonate, potassium carbonate, sodium phosphate and potassium phosphate.

 In the reaction, the compound (4) is usually used in an amount of 1 to 2 mol, the palladium catalyst is usually used in an amount of 0.001 to 0.1 monol, and the base is usually used in an amount of 2 to 20 mol per 1 mol of the compound (3). Is done.

 The reaction temperature of the reaction is usually in the range of 20 to 120 ° C, and the reaction time is usually in the range of 0.1 to 24 hours.

 After completion of the reaction, the compound of the present invention represented by the formula (2) is subjected to post-treatment operations such as pouring the reaction mixture into water, extracting with an organic solvent, and drying and concentrating the obtained organic layer. Can be isolated. The isolated compound of the present invention represented by the formula (2) can be further purified by chromatography, recrystallization and the like.

 Among the compounds of the present invention, a compound represented by the formula (5) (hereinafter referred to as compound (5)

. )

[Wherein, RR \ R ⁵ , m and n represent the same meaning as described above. ]

Is a compound represented by the formula (6) (hereinafter, referred to as compound (6)):

[Wherein, RRR ⁵ , m and n represent the same meaning as described above. ] And a metal cyanide.

 The reaction may be carried out in the presence of a solvent. Examples of the solvent used include nitriles such as acetonitrinole, propionitrile, methyl-tert-butylatenoate, ethylene glycolone methinoleatenoate, tetrahydrofuran, 1 Ethers such as 1,4-dioxane; amides such as N, N-dimethylformamide; and sulfoxides such as dimethyl sulfoxide.

 Examples of the metal cyanide used in the reaction include potassium cyanide, sodium cyanide and the like. The metal cyanide is usually used in a proportion of 1 mol to 10 mol per 1 mol of the compound (6).

 In the reaction, a crown ether such as 18_crown-16, dibenzo-18-crown-16, dicyclohexano 18-crown-16, 15-crown-15 may be used in the reaction, if necessary. In such a case, the crown ether is usually used in a proportion of 1 mol to 10 mol per 1 mol of the compound (6).

 The reaction temperature of the reaction is usually in the range of 20 to 150 ° C, and the reaction time is usually in the range of 1 to 48 hours.

 After completion of the reaction, for example, the reaction mixture is poured into water, extracted with an organic solvent, and the obtained organic layer is subjected to post-treatment operations such as drying and concentration to obtain the present invention represented by the formula (5). The compound can be isolated. The isolated compound of the present invention represented by the formula (5) can be further purified by chromatography, recrystallization and the like.

 Among the compounds of the present invention, a compound represented by the formula (7) (hereinafter referred to as compound (7)

. )

[Wherein, R ¹ R ² , R ⁵ , m and n represent the same meaning as described above, and R ⁴¹ represents a C 1 -C 4 alkyl group. ]

The compound (6), a metal alkoxide compound: R ⁴ in ¹ OM [wherein, R ^{4 1} is said In the same meaning, M represents an alkali metal. And a reaction with each other.

The reaction is usually performed in a solvent. Examples of the solvent used in the reaction include ethers such as methanol, tert-butylinoleate, ethylene glycolone resin methinoleate, tetrahydrofuran, 1,4-dioxane and the like; N, N-dimethylformamide and the like. Or an alcohol corresponding to the metal alkoxide compound used: R ⁴¹ 〇H wherein R ⁴¹ has the same meaning as described above. ].

Metal alkoxide compound used in the reaction: R ⁴¹ OM is an alcohol: R ⁴¹ OH and an alkali metal (eg, lithium, sodium, potassium) or an alkali metal hydride (eg, lithium hydride, sodium hydride, hydrogen) Chemical strength). Usually, sodium alkoxide is used. The metal alkoxide compound is generally used in a proportion of 1 mol to 5 mol per 1 mol of compound (6).

 The reaction temperature of the reaction is usually in the range of 0 to 100 ° C, and the reaction time is usually in the range of 1 to 48 hours.

 After completion of the reaction, for example, the reaction mixture is poured into water and extracted with an organic solvent, and the obtained organic layer is subjected to a post-treatment operation such as drying and concentration to obtain the present invention represented by the formula (7). The compound can be isolated. The isolated compound of the present invention represented by the formula (7) can be further purified by chromatography, recrystallization and the like.

Among the compounds of the present invention, a compound represented by the formula (9) (hereinafter, referred to as compound (9)) can be produced, for example, by a route shown in the following scheme.

 (9

Wherein, RR ^2, R \ m and n are as defined above, R ^{4 2} is C: represents a C 4 alkyl group. ]

Process 1-1

 The compound represented by formula (8) (hereinafter referred to as compound (8)) can be produced by reacting compound (6) with dialkyl malonate in the presence of a base.

 The reaction is usually performed in a solvent. Examples of the solvent used in the reaction include ether's such as methylenolate tert-butylinoleatene, ethylene glycolone resin methinoleatenole, tetrahydrofuran, 1,4-dioxane, and N, N-dimethylhonolemamide. Amides. Examples of the base used in the reaction include alkali metal hydrides such as sodium hydride.

 In the reaction, the dialkyl malate is generally used in a proportion of 2 to 8 mol, and the base is usually used in a proportion of 2 to 8 mol per 1 mol of the compound (6).

 The reaction temperature of the reaction is usually in the range of 0 to: 150 ° C, and the reaction time is usually in the range of 1 to 48 hours.

After completion of the reaction, for example, the reaction mixture is poured into acidic water (for example, hydrochloric acid, aqueous solution of citric acid, etc.), extracted with an organic solvent, and subjected to a post-treatment operation such as drying and concentration of the obtained organic layer. The compound (8) can be isolated. Isolated compound ( 8) can be further purified by chromatography, recrystallization and the like. Process 1 1 2

 Compound (9) can be produced by thermally decomposing compound (8).

 The reaction is usually carried out in a strong acid aqueous solution (hydrochloric acid, sulfuric acid, etc.), the reaction temperature is usually in the range of 50 to 100 ° C, and the reaction time is usually in the range of 0.1 to 24 hours. Thereafter, the compound (9) can be isolated by performing post-treatment operations such as neutralizing the reaction solution, extracting with an organic solvent, and drying and concentrating the obtained organic layer. The isolated compound (9) can be further purified by chromatography, recrystallization and the like.

 The compound represented by the formula (A-3) (hereinafter, referred to as compound (A-3)) can be produced, for example, by a route shown in the following scheme.

 (A-3)

[Wherein, RR ² , X ¹ and m have the same meanings as described above; ⁶ represents a C 1 -C 4 alkyl group. ]

Process 2-1

The compound represented by the formula (A-2) (hereinafter, referred to as compound (A-2)) is a malonic acid ester ロ ン conjugated compound represented by the formula (A-1) (hereinafter, referred to as compound (Α-1) ) And 2-aminoimidazole hydrochloride in the presence of a base. can do.

 The reaction can also be performed in the presence of a solvent. Examples of the solvent used include aromatic hydrocarbons such as xylene and mesitylene and acid amides such as N, N-dimethylformamide.

 Examples of the base used in the reaction include triptylamine, 1,8-diazabicyclo [5.4.0] indeck-17-ene (hereinafter, referred to as DBU), 1,5-diazabicyclo [4.3.0] ] Organic bases such as non-5-ene (hereinafter referred to as DBN).

 In the reaction, 2-aminoimidazolone hydrochloride is usually used in a proportion of 0.5 to 2 mol, and a base is usually used in a proportion of 1.5 to 3 mol, per 1 mol of the compound (A-1). The reaction temperature of the reaction is usually in the range of 50 to 200 ° C, and the reaction time is usually in the range of 0.5 to 24 hours.

 After completion of the reaction, for example, the reaction mixture is partitioned between an organic solvent and water (or alkaline water), and a precipitate formed by adding an acid such as hydrochloric acid to the obtained aqueous layer (after concentrating as necessary). The compound (A-2) can be isolated by filtering. The compound (A-12) can be isolated in the form of a salt by filtering the reaction mixture as it is or, if necessary, concentrating it.

 The reaction of Step 2-1 can be carried out similarly by using 2-aminoimidazole sulfate instead of 2-aminoimidazole hydrochloride.

Process 2-2

 Compound (A-3) can be produced by reacting compound (A-2) with a halogenating agent.

 The reaction can be performed in the presence of a solvent. Examples of the solvent to be used include aromatic hydrocarbons such as toluene and xylene, nitrinoles such as acetonitrile and propionitolinole, and halogenated hydrocarbons such as 1,2-dichloroethane.

As the halogenating agent used in the reaction, for example, an organic phosphorus compound: In the formula, X ¹ has the same meaning as described above. Specific examples include phosphorus oxychloride and the like]. The halogenating agent used in the reaction is usually 2 mol to an excess amount per 1 mol of the compound (A-2).

 For the reaction, N, N-dimethylaniline, N, N-getylaniline, triethynoleamine, diisopropylethylamine, pyridine, 5-ethyl

Organic bases such as 2-picoline, DBU, and DBN can also be allowed to coexist. The amount of the base used is usually 0.1 to 5 mol per 1 mol of the compound (A-2). .

 The reaction temperature of the reaction is usually in the range of 50 to 150 ° C, and the reaction time is usually in the range of 1 to 48 hours.

 After completion of the reaction, for example, the reaction mixture is directly concentrated, and the obtained residue is separated with an organic solvent and a weakly basic aqueous solution (for example, aqueous sodium hydrogen carbonate). The compound represented by the formula (A-3) can be isolated. The isolated compound represented by the formula (A-3) can be further purified by chromatography, recrystallization, or the like.

 The compound represented by the formula (B-3) (hereinafter, referred to as compound (B-3)) can be produced, for example, by a route shown in the following scheme.

[Wherein, RR ² , R ⁶ , X ¹ and m represent the same meaning as described above, and R ⁴³ represents a C1-C4 alkyl group. ]

Process 3-1 A compound represented by the formula (B-2) (hereinafter, referred to as compound (B-2)) is represented by the formula (B-1):] 3-ketoester compound (hereinafter, referred to as compound (B-1)) ) And 2-aminoimidazole hydrochloride in the presence of a base.

 The reaction can be performed in the presence of a solvent. Examples of the solvent used include aromatic hydrocarbons such as xylene and mesitylene and acid amides such as N, N-dimethylformamide.

 Examples of the base used in the reaction include organic bases such as triptylamine, DBU and DBN. '

 In the reaction, 2-aminoimidazole hydrochloride is usually used in a proportion of 0.5 to 2 mol, and a base is usually used in a proportion of 1.5 to 3 mol per 1 mol of the compound (B-1). The reaction temperature of the reaction is usually in the range of 50 to 200 ° C, and the reaction time is usually in the range of 0.5 to 24 hours.

 After completion of the reaction, for example, the reaction mixture is partitioned between an organic solvent and water (or alkaline water), and a precipitate formed by adding an acid such as hydrochloric acid to the obtained aqueous layer (after concentrating as necessary). Compound (B-2) can be isolated by filtration. The compound represented by the compound (B-12) can be isolated in the form of a salt by filtering the reaction mixture as it is or, if necessary, concentrating it.

 The reaction of Step 3-1 can be carried out in the same manner by using 2-aminoimidazole sulfate instead of 2-aminoimidazole hydrochloride.

Process 3-2

 Compound (B-3) can be produced by reacting compound (B-2) with a halogenating agent. '

 The reaction can also be performed in the presence of a solvent. Examples of the solvent to be used include aromatic hydrocarbons such as toluene and xylene, nitriles such as acetoethryl and propionitrile, and halogenated hydrocarbons such as 1,2-dichloropropane. ·

As the halogenating agent used in the reaction, for example, an organic phosphorus compound: ΡΟΧ [wherein, X ¹ has the same meaning as described above. More specifically, for example, can give.

 The amount of the halogenating agent used in the reaction is usually 1 mol to an excess amount per 1 mol of the compound represented by the formula (B-2).

 If necessary, an organic base such as N, N-dimethylaniline, N, N-getylaniline, triethylamine, diisopropylethylamine, pyridine, 5-ethyl-2-picoline, DBU, or DBN may be used in the reaction. In this case, the amount of the base is 0.1 to 5 monoles per 1 mol of the compound represented by the formula (B-2).

 The reaction temperature of the reaction is usually in the range of 50 to 150 ° C, and the reaction time is usually in the range of 1 to 48 hours.

 After completion of the reaction, post-treatment operations such as concentrating the reaction mixture as it is, then separating the residue with an organic solvent and a weakly basic aqueous solution (for example, aqueous sodium hydrogen carbonate), and concentrating the obtained organic layer are performed. By this, compound (B-3) can be isolated. The isolated compound (B-3) can be further purified by chromatography, recrystallization, or the like.

 The compound (4) can be produced, for example, according to the method described on page 68 of Org Anic Synthes Synthes Colls. Compound (A-1) can be produced, for example, according to the method described in Japanese Patent Application Laid-Open No. 2-202876, Chemistry Let Lets, 1981, p. 367.

 The compound (B-1) can be prepared, for example, according to the method described in, for example, Organic Synthesis Collective Volume 2, pp. 487-489 and 284-286, Japanese Patent Application Laid-Open No. 60-255788. It can be manufactured according to it.

 2-Aminoimidazole sulfate and hydrochloride are known from J. Chem. Soc., 1956, p. 307, J. Org. Chem., 1964, p.

Next, specific examples of the compound of the present invention are shown below. A compound represented by the formula shown below.

の続き）

Continued)

の続き）

Continued)

の続き）

Continued)

の続き）

Continued)

1の続き）

1 continuation)

の続き）

Continued)

1の続き）

1 continuation)

1の続き）

1 continuation)

(表 1の続き)

(Continuation of Table 1)

の続き）

Continued)

1の続き）

1 continuation)

の続き）

Continued)

MOiO / COdf / X3d εεΐ "68θ / εο OAV 1 continuation)

の続き）

Continued)

GO CO CO oo CO CO

GO CO CO oo CO CO

 n Cn

 1 1 I I 1 1 1

 , c

 l

 ^ cj ^ irj ^ ir]

o

1 1 continuation)

¾)0 - ¾3 13 Τ3ΐΡ-9^

¾) 0-¾3 13 Τ3ΐΡ-9 ^

 ¾0 ID DTP-9 '

¾ο-ε ¾3 TO DTP-9 '

¾)-¾3 TO Τ0ΐΡ-9 ^

Ό-Ζ ¾3 TO ΐΟΐΡ-9 ^ το-ε ¾3 TO Ϊ3ΪΡ- 9 '

¾0 TO ΐ3ΐΡ-9 ^

¾0 TO DTP-9 '

¾α-ε ¾0 TO Τ3ΐΡ-9 ^

¾. -TO TOTP-9 '^ One ID Τ3ΐΡ-9 ^

¾30-Z 13 d-9

¾οο-ε ¾0 13 -9

¾D0- ¾3 TO d-9

 ¾3 TO d-9

¾ο-ε TO Λ-9

 ¾tsu 13 d-9 ld-Z TO d-9 ΐο-ε ¾0 13 d-9

Ό- ¾3 TO d-9

¾. -2 ¾3 13

 ¾ο-ε TO d-9

 Pit 13 d-9

T3 d-9 εΗ30-2 ¾3 d «ί-9 u ( _s a)

nOZO / £ Od £ / ∑Jd

Continued)

(表 1の続き）

(Continuation of Table 1)

(表 1の続き）

(Continuation of Table 1)

ΐΟ-8 ¾D0 d

ΐΟ-8 ¾D0 d

 Poo- ¾00 d dW-9 '

¾α-2 ¾30 d

 ¾ο-ε ¾30 d dW-9 '

¾tsu-¾30 d

 -¾30 d

 ¾30-2 ¾30 Ό ldW-9 '

¾30-ε ¾30 Ό ldW-9'f

¾) 0- ¾30 Ό I3TP-9 ^

 ¾. 0 ID Ϊ3ΪΡ-9 '

¾30 TO

 0 つ 0 ID Τ0ΐΡ-9 ^

Ό-Ζ ¾. 0 TO ΐΟΐΡ-9'ϊ ⁷ ιο-ε ¾30 13 ldW-9 '

¾00 13

 eRd-Z ¾30 TO ΐ3ΐΡ-9 ^

¾ο-ε ¾30 13 Ϊ3ΪΡ-9 '

¾. 0 Ό lD -9'f

-¾D0 13 O -9 '

¾D0 13 d-9

¾οο-ε ¾30 ID d-9

P0-¾30 T3 d-9

 ¾30 10 d-9

¾α-ε ¾00 TO d-9

¾D-¾30 d-9

^U ( _S H)

If nOZO / £ Od £ / ∑Jd (Continuation of Table 1)

¾0-2 ¾30 TO -

¾0-2 ¾30 TO-

¾30 TO-

¾)-¾30 TD-

-Po ~ 0 TO-

¾00 d one

 ¾οο-ε ¾30 d one

 ¾D0-¾00 ά one

 ¾30 ή-

¾30 d one

 ¾00 d-

¾30 i-ΐ3-ε ¾30 d-

¾30 ή one

 ¾αο d-

¾ο-ε ¾30 d-

¾)-¾30 one

 -¾30 ή-

¾00 TO O-

¾οο-ε ¾30 TO lO-f

 One. -¾30 Ϊ3 Ό-

¾. 0 Ώ-

¾00 ΐθ Ό- Tsu- ¾30 Ό

 ¾30 Ό ΐ. -,

 το-ε ¾00 13 13-

^U ( _S ) „Η ^m (xH)

6

Pl0Z0 / £ 0d £ / 13d ε 680 / εο OAV (Continuation of Table 1)

(表 1の続き)

(Continuation of Table 1)

 6 ^ m I

 Z

Moro / codf / i3d ££ t6 0 / £ 0 OAV ¾D0- NO TO D-

NO TO

NO 10 ΐ-sdd- NO TO 13- ^

 NO TO Ό-f

 ιο-ε N3 13 D-

Id- NO TO TO-

N3 10 Ϊ3-

¾3-e N3 13 1-

NO TO Ϊ3-one NO 13 ΐ-

¾30-2 NO Λ d-

¾οο-ε NO d Λ-

¾30- NO d d-f

 One-2 NO ή d-f

 ¾ο-ε NO d d-f

 NO d d- ld-Z N3 Λ d- ΐο-ε NO d ή-Ψ

 ΐ つ-、 NO d d-

¾ つ-2 NO Λ d-

. ¾ο-ε NO d d-

¾3-, NO d d-

NO d d-f

 )

PlOZO / £ Od £ / 13d ε 680 / εο OAV (Continuation of Table 1)

(表 1の続き）

(Continuation of Table 1)

(表 1の続き)

(Continuation of Table 1)

(表 1の続き）

(Continuation of Table 1)

(表 1の続き)

(Continuation of Table 1)

(R ¹ ) ^ R ² R ⁴ (R ⁵ ) _n -FF CH (CH ₃ ) ₂ 1 -FF CH (CH ₃ ) ₂ 4-CH ₃ -FF CH (CH ₃ ) ₂ 4-C1 -FF 0C _{2 H 5 - -FF 0C 2 H 5} 4-CH 3 -FF 0C 2 H 5 4- CI -FF 0 (CH 2) 2 CH 3 one _{-FF 0 (CH 2) 2 CH} 3 4-CH 3 -FF 0 _{(CH 2) 2 CH 3 4} -C1 -FF 0CH (CH 3) 2 one _{-FF 0CH (CH 3) 2 4-} CH 3 -FF 0CH (CH 3) 2 4- CI, 6-diF F CH 3 - , 6-diF F CH ₃ 4-CH ₃ , 6-diF F CH ₃ 4- CI, 4-diF F CH ₃ 1, 4-diF F CH ₃ 4-CH ₃ , 4-diF F CH ₃ 4-C1 , 5-diF F CH ₃ -1,5-diF F CH ₃ 4-CH ₃ , 5-diF F CH ₃ 4-C1,, 4,6-triF F CH ₃

, 4,6-triF F CH ₃ 4-CH ₃ , 4,6-triF F CH ₃ 4-CI i OAV

 ◦ ◦ X

oooo ぎ ¾ o c¾ t¾ PL, c¾

¾3

ΐ.

The following are examples of plant diseases which the compound of the present invention has control effect.

 Phiicularia oryzae, Cochliobolus miyabeanus, Rhizoctonia solani;

 Wheat spikelets (Erysiphe graminis), redness, rot (Gibbere 丄 la zeae), rust (Puccinia striiformis, P. graminis, P. recondita, P. hordei), ¾ rot (Typhula sp., Micronectriella nivalis), smut (Ustilago tritici, U. nuda), black smut (Tilletia caries), eye spot (Pseudocercosporella herpotrichoides), scald (Rhynchosporium secalis), leaf blight (Septoria tritic 內) (Leptosphaeria nodorum);

 Sunspots of citrus, disease (Diaporthe citri), soybean sickness (Elsinoe fawcetti), fruit rot (Penicillium digitatum, P. italicum;

 Apple morilia disease (Sclerotinia mali), rot (Valsa mali), udon noodles (Podosphaera leucotricha), spotted deciduous leaves Γhei (Alternaria mali) Kuroboshi (Venturia maequa 丄 isno;

 Pear of the pear (Venturia nashicola, V. pirina), black spot (Alternaria kikuchiana) ^ red disease (Gymnosporangium haraeanum);

 Peach ash disease (Sclerotinia cinerea), scab (Cladosporium carpophilum), Phomopsis rot (Phomopsis sp.);

 Grape scab (Elsinoe ampelina), rot (Glomerella cingulataj), powdery mildew (Unc inula necator), rust (Phakopsora ampe 丄 opsiais), bukkake rot (Guignardia bidwellii), and bets and pings (Plasmopara viticola) );

 Gloeosporium kaki, Visitor leaf ^ 內 (Cercospora kaki, Mycosphaerella nawae;

 Anthracnose (colletotrichum lagenarium), powdery mildew

(Sphaerothecafuliginea), O ¾ ¾ ^ (Mycospnaerella melonis), harmful 1 | Hei (Fusarium oxysporum), bee ;; Hee (Pseu operonospora cubensis), ¾ (Phytophthora sp.), Seedling (Pythium sp.)

Tomato no Rinhei (Alternaria solani), Scab (Shu adosporium fulvumj, Plague (Phytophthora infestans);

 Eggplant disease (Phomopsis vexans), powdery mildew (Erysiphe cichoracearum) on eggplant; Brassica vegetable black spot (Alternaria japonica), white spot (Cercosporella brassicae;

 Green onion rust (Puccinia allii), soybean purpura (Cercospora kikuchii), black rot (Elsinoe glycines), black spot (Diaporthe phaseolorum var. Sojae); Kingen's anthracnose (Colletotrichum lindemthianum);

 Black rot of laccasei (Cercospora personata brown spot) (Cercospora arachidicola);

 Endo powdery mildew (Erysiphe pisi);

 Potato summer plague (Alternaria solani), plague (Phytophthora infestans);

 Sphaerotheca humuli;

 Tea net rot (Exobasidium reticulatum); Hakuboshi hei (Elsinoe leucospila), tobacco scab (Alternaria longipes), Tsudonko E (Erysiphe cichoracearum), Charmeso bat (Colletotrichum tabacum), Downy mildew (Peronospora tabacina) disease (Phytophthora nicotianae);

 Brown spot of sugar beet (Cercospora beticola;

 Nora scab (Diplocarpon rosae), powdery mildew (Sphaerotheca pannosa); chrysanthemum spot of chrysanthemum (Septoria chrysanthemi- indici), white rot (Puccinia noriana);

Gray rot (Botrytis cinerea), sclerotium (Sclerotinia sc 丄 erotiorunv ₀ ) on various crops

The compound of the present invention exerts a bactericidal effect even when it is applied to plants or soil, but is usually used in the form of a bactericidal composition containing the compound of the present invention and a suitable carrier. The germicidal composition of the present invention is usually prepared by mixing the compound of the present invention with a solid carrier and / or a liquid carrier, and adding a surfactant or other formulation aid as necessary, to prepare an emulsion, a wettable powder, It is prepared as preparations such as wettable powders, flowables, powders, and granules. In these preparations, the compound of the present invention is usually contained at 0.1 to 90% by weight.

 Examples of the solid carrier used in the formulation include kaolin clay, attaparjait clay, bentonite, montmorillonite, acid clay, pyrophyllite, tanolek, diatomaceous earth, calcite and other minerals, corn cob powder, walnut shell powder, etc. Fine powders or granules made of natural organic substances, synthetic organic substances such as urea, salts such as calcium carbonate and ammonium sulfate, and synthetic inorganic substances such as synthetic hydrated silicon dioxide.Examples of the liquid carrier include xylene, Aromatic hydrocarbons such as alkylbenzene, methylnaphthalene, etc., alcohols such as 2-propanol, ethylene glycol, propylene glycol, cellosolve, ketones such as acetone, cyclohexanone, isophorone, soybean oil, cottonseed oil, etc. Vegetable oil, petroleum aliphatic hydrocarbon , Ester le include dimethyl sulfoxide, Asetonitoriru and water.

 Surfactants include, for example, alkyl sulfates, alkylaryl sulfonates, dialkyl sulfosuccinates, polyoxyethylene alkylaryl etherenolate phosphate, lignin snolephonate, naphthalene sulfonate polyaldehyde polycondensates And the like, and nonionic surfactants such as polyoxyethylene alkenyl oleoretinol, polyoxyethylene olenoquinole polyoxypropylene block copolymer, and sorbitan fatty acid ester.

 Other pharmaceutical auxiliaries include, for example, water-soluble polymers such as polybutyl alcohol and polybutylpyrrolidone, gum arabic, alginic acid and its salts, polysaccharides such as CMC (Ruboxymethylcenorellose), xanthan gum, and aluminum magnesium.無機 Inorganic substances such as silicate and alumina sol, preservatives, coloring agents and stabilizers such as PAP (isopropyl acid phosphate) and BHT. By treating the plant with the fungal composition of the present invention, the plant can be protected from plant diseases, that is, plant diseases can be controlled. Further, by treating the soil with the fungicidal composition of the present invention, plants growing on the soil can be protected from plant diseases, that is, plant diseases can be controlled.

When the fungicidal composition of the present invention is subjected to foliage treatment on a plant, or the fungicidal composition of the present invention When applied to soil, the amount of treatment can be varied depending on the type of crop as a plant to be controlled, the type of disease to be controlled, the degree of occurrence of the disease to be controlled, formulation, treatment time, weather conditions, etc. However, the compound of the present invention is usually 1 to 500 g, preferably 5 to 100 g per l′ OOOO m ² .

 Emulsions, wettable powders, flowables, etc. are usually treated by diluting with water and spraying. In this case, the concentration of the compound of the present invention is generally in the range of 0.001 to 3% by weight, preferably in the range of 0.0 'to 5-1% by weight. Dusts, granules, etc. are usually processed without dilution.

 When the fungicidal composition of the present invention is applied to a plant, the plant can be protected from plant diseases by treating the plant at the seed stage. As a specific method, for example, a method of immersing a seed in a fungicidal composition of the present invention prepared by adjusting the concentration of the compound of the present invention to 1 to 100 ppm, The method includes spraying or smearing the fungicidal composition of the present invention at a concentration of l to 100 ppm, and coating the seed of a plant with the fungicidal composition of the present invention.

 The method for controlling plant diseases of the present invention is generally carried out by applying an effective amount of the bactericidal composition of the present invention to a plant in which the occurrence of a disease is predicted or a soil in which the plant grows. The fungicidal composition of the present invention is generally used as an agricultural / horticultural fungicide, that is, a fungicide for controlling plant diseases in fields, paddy fields, orchards, tea fields, pastures, lawns, and the like. The fungicidal compositions of the present invention can also be used with other fungicides, insecticides, acaricides, nematicides, herbicides, plant growth regulators and / or fertilizers.

Such fungicides include, for example, propiconazole, triazimenol, prochloraz, penconazo monole, tebuconazonole, funoresilazonole, dinicozonore, bromconazonole, epoxyconazo monole, difuenoconazonole, ciproconazole Azole propagating compounds such as triflumizole, tetraconazole, microbutanol, fenbuconazole, hexaconazole, fluquinconazole, triconazole, bitertanol, imazalil and flutoriaphor; fenpropimorph, tridemorph and phen Cyclic amine fungicidal compounds such as providin; benzimidazole fungicidal compounds such as carbendazim, benomyl, thiabendazole, and thiophane monomethyl; Shimidon; Shipurodi two Nore; Pyrimethanil; Jetofencarp; Thiuram; Fluazinam; Mancozep; Iprodione; Bink zoline; Chlorothaloninole; Kyabtan; Mepanipyrim; Fenpiclonil; Fludioxonil; Zikuguchi fluanid; Trifloxystrobin; Picoxis trobin; Pyraclostrobin; N-Methyl Λ ^ -α-Methoxyiminor 2-[((2,5-dimethylphenoxy) methyl] phenylacetamide; Spiroxamine; Quinoxyfen; Fenhexamide; famoxadone; fenamidone (RP-407213); iplovalicarp; bentivarivaricalp; schazofuamide; nicobifen; metolaphenone and sifu ^ enamide. Hereinafter, the present invention will be described in more detail with reference to Production Examples, Formulation Examples, Test Examples, and the like, but the present invention is not limited to these Examples.

 First, Production Examples of the compound of the present invention will be described.

-(2, 4, 6—trinoleolophenyl) imidazo [1

0.95 g, 0.49 g of 4-methylphenylboronic acid, 1.91 g of potassium phosphate hydrate, {1,1,1-bis (diphenylphosphino) phenyl) diclodium palladium ( II) 73 mg of methylene chloride complex and 15 ml of ethylene glycol dimethyl ether were mixed, and the mixture was heated under reflux under a nitrogen atmosphere for 6 hours. Thereafter, the reaction mixture was allowed to cool to room temperature, filtered, and the filtrate was concentrated. The residue was dissolved in chloroform and washed successively with water, a 10% aqueous sodium hydroxide solution, water, a saturated aqueous ammonium chloride solution and water. The organic layer was dried over anhydrous sodium sulfate and concentrated. The residue was subjected to silica gel column chromatography, washed with a mixture of methyl tert-butyl ether and hexane, and treated with 5_ (4-methylphenyl)- ― (2,4,6-trifluorophenyl) 1 7-cycloimidazo [1,2—a] pyrimidine

 (Hereinafter referred to as the present compound (1).) 0.28 g was obtained.

 Melting point: 155.1 ° C

 -i-NMR (CDC 13, TMS) δ (ρ ρ m): 239 (3H, s), 6.63 (2Η, dd, J = 7.1 Hz, 8.6Hz), 7 20- 7.25 (4H, m), 7.25 (1H, d, J = 1.5Hz), 7.75 (1H, d, J = 1.5Hz)

Production Example 2

5,7-dichrolic 6- (2,4,6-triphnoleolopheninole) imidazo [1,2-a] pyrimidine 0.48 g, phenylboronic acid 0.27 g, carbonated rim 0. A mixture of 62 g, {1,1,1-bis (diphen-norophosphino) fuecsen} dichloroparadium (II) chloride methylene complex (3 lmg) and toluene (10 ml) was heated and refluxed for 13 hours under a nitrogen atmosphere. Thereafter, the reaction mixture was allowed to cool to room temperature and then filtered. The filtrate was poured into water and extracted with toluene. The organic layer was washed successively with water, a 10% aqueous sodium hydroxide solution, water, a saturated aqueous sodium chloride solution and a saturated saline solution, dried over anhydrous sodium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give 5-phenyl-6- (2,4,6-trifluorophenyl) -17-chloroimidazo [1,2-a] pyrimidine

 (Hereinafter referred to as the present compound (2).) 0.1 lg was obtained.

 Melting point: 139.4 ° C

 — NMR (CDC 13, TMS) δ (ρ ρ m): 663 (2H, dd, J = 7Η Η, 8Hz), 7.24 (1Η, s), 7.3—7.4 (2H, m ), 7.4-7.5.5 (m, 3Η), 7.78 (1Η, s)

Production Example 3

5,7-dichloro-1-6- (2,4,6-trinoleolopheninole) imidazo [1,2, -a] pyrimidine 0.48 g, 4-monoclofenylporonic acid 0.28 g, A mixture of 0.62 g of potassium carbonate and {1,1,1-bis (diphenylphosphino) phenol} dichloropalladium (II) 31 mg of a methylene complex of sodium chloride and 10 ml of ethylene glycol dimethyl ether was mixed with nitrogen. The mixture was refluxed under heating for 6 hours. Thereafter, the reaction mixture was allowed to cool to room temperature, filtered, and the filtrate was concentrated. The residue was dissolved in chloroform and washed sequentially with water, 10% aqueous sodium hydroxide, water, saturated aqueous sodium chloride, and water. The organic layer was dried over anhydrous sodium sulfate and concentrated. The residue was subjected to silica gel column chromatography, and the obtained crude product was mixed with 5 ml of ethyl alcohol and 5 ml of aqueous ammonia, and refluxed with heating for 3 hours. After concentrating the reaction mixture, the residue was subjected to silica gel column chromatography to give 5- (4-chlorophenyl) -6- (2,4,6-trifluorophenyl) -17-chloroimidazo [1 , 2-a] pyrimidine

 (Hereinafter referred to as the present compound (3).) 0.16 g was obtained.

 Melting point: 156.3 ° C

 One stroke R (CDC 13, TMS) δ (p pm): 6.66 (2H, dd, J = 7Hz, 8Hz), 7.20 (1H, d, J = 1Hz), 7.29 (2H, d, J = 8Hz), 7.84 (2H, d, J = 8Hz), 7.79 (1H, d, J = 1Hz)

Production Example 4

5,7-dichloro-6- (2,4,6-trifluorophenyl) imidazo [1,2-a] pyrimidine 0.48 g, 4-methoxyphenylboronic acid 0.27 g, potassium phosphate hydrate 0 96 g, {1,1,1-bis (diphenylphosphino) erocene) dichloropalladium (II) 37 mg of methylene chloride complex and ethylene glycol dimethyl ether omom 1 were mixed and heated under nitrogen atmosphere for 4 hours to reflux. did. Thereafter, the reaction mixture was allowed to cool to room temperature, filtered, and the filtrate was concentrated. The residue was dissolved in a mouth-mouth form and washed successively with water, a 10% aqueous sodium hydroxide solution, water, a saturated aqueous sodium chloride aqueous solution, and water. The organic layer was dried over anhydrous sodium sulfate and concentrated. The residue was subjected to silica gel gel chromatography. The obtained crude product was dissolved in ethyl alcohol (2 ml), hydrazine monohydrate (34 mg) was added, and the mixture was stirred at room temperature for 2 hours. The reaction solution was poured into water, and the deposited precipitate was collected by filtration and subjected to silica gel column chromatography to give 5- (4-methoxyphenyl) -16- (2,4,6-trifluorophenyl) One 7-cloth imidazo [1, 2-a] pyrimidine

 (Hereinafter referred to as the present compound (4).) 0.15 g was obtained.

 Melting point: 170 .. 4 ° C

 ^ -NMR (CDC 1 a, TMS) δ (ρ pm): 3.84 (3Η, s), 6.65 (2Η, dd, J = 7Hz, 8Hz), 6.93 (2H, d, J = 1Hz, 7.27 (2H, d, J = 9Hz), 7.28 (1H, d, J = 2Hz), 7.76 (1H, d, J = 2Hz)

Production Example 5

5,7-dichloro-6- (2,4,6-trifluorophenyl) imidazo [1,2-a] pyrimidine 0.48 g, 4- (trifrenoleolomethinole) pheninolepolonic acid 0.34 g, 0.96 g of potassium phosphate hydrate, {1,1-bis (diphenyl phosphino) phenoctene} dice palladium (II) methylene chloride complex (37 mg) and ethylene glycol dimethyl ether (10 ml) were mixed and mixed under a nitrogen atmosphere. Heated to reflux for an hour. Thereafter, the reaction mixture was allowed to cool to room temperature, filtered, and the filtrate was concentrated. The residue was dissolved in chloroform, and washed sequentially with water, a 10% aqueous sodium hydroxide solution, water, a saturated aqueous ammonium chloride solution, and water. The organic layer was dried over anhydrous sodium sulfate and concentrated. The residue was subjected to silica gel column chromatography, washed with hexane, and treated with 5- (4- (tri-phenolic phenyl) phenyl) -6- (2,4,6-trifluorophenol). 1) 7-Chloroimidazo [1, 2-a] pyrimidine

 (Hereinafter referred to as the present compound (5).) 89 mg was obtained.

 Melting point: 123.5 ° C

ΙΗζ), 7. 51 (2H， d, J =8Hz)， 7. 75 (2Η， d, J =8Hz)， 7. 80 (1H， d, J = lHz) 'H-NMR (CDC 13, TMS) δ (ρ pm): 667 (2H, dd, J

ΙΗζ), 7.51 (2H, d, J = 8Hz), 7.75 (2Η, d, J = 8Hz), 7.80 (1H, d, J = lHz)

Production Example 6

5,7-Dichloro mouth_6_ (2,4,6-trifluorophenyl) imidazo [1,2-a] pyrimidine 0.48 g, 3-Cro mouth phenylboronic acid 0.28 g, potassium phosphate water 0.96 g of the hydrate, {1,1, —bis (diphenylphosphino) phenoctene} dicyclopentalium (II) 37 mg of methylene complex of salt and 1 ml of ethylene dalicol dimethyl ether were mixed, The mixture was refluxed for 4 hours under a nitrogen atmosphere. Thereafter, the reaction mixture was allowed to cool to room temperature, filtered, and the filtrate was concentrated. The residue was dissolved in black-mouthed form and washed sequentially with water, 10% aqueous sodium hydroxide, water, saturated aqueous ammonium chloride and water. The organic layer was dried over anhydrous sodium sulfate and concentrated. The residue was subjected to silica gel column chromatography. The obtained crude product was dissolved in ethyl alcohol (2 ml), hydrazine monohydrate (30 mg) was added, and the mixture was stirred at room temperature for 2 hours. The reaction solution was poured into water and extracted with black-mouthed form. The organic layer was washed successively with a saturated aqueous solution of ammonium chloride and water, and then concentrated. The residue was subjected to silica gel column chromatography to give 5- (3-chlorophenyl) -6- (2,4,6-trifluorophenyl) -17-chloroimidazo [1,2-a] pyrimidine

 (Hereinafter referred to as the present compound (6).) 28 mg was obtained.

 Melting point: 176.0 ° C

 NMR (CDC 1 a, TMS) δ (p pm) 6.6-6.8 (m, 2H), 7.21 (1H, d, J = 1 Hz), 7.20-7 25 (1 H, m), 7

36 (1H, s), 7.41 (1H, t, J = 8Hz), 7.45-7.50 (1H, m), 7.80 (1H, d, J = 1Hz)

Production example 7 '

 5,7-dichroic 6- (2,4,6-trifluoropheninole) imidazo [1,2-a] pyrimidine 0.48 g, 2-methylphenylporonic acid 0.25 g, potassium phosphate 0.96 g of hydrate, {1,1, -bis (diphenylphosphino) phenoctene} dichloropalladium (II) 37 mg of methylene chloride complex and 10 ml of ethylene glycol dimethyl ether were mixed under nitrogen atmosphere. Heated to reflux for 5 hours. Thereafter, the reaction mixture was allowed to cool to room temperature, filtered, and the filtrate was concentrated. The residue was dissolved in chloroform and washed successively with water, a 10% aqueous sodium hydroxide solution, water, a saturated aqueous ammonium chloride solution and water. The organic layer was dried over anhydrous sodium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give 5- (2-methylpheninole) -6- (2,4,6-trifluorophenyl) -17-chloroimidazo [1,2-a] pyrimidine

(Hereinafter, referred to as the present compound (7).) 0. to give the 12 g _c Melting point: 173.9 ° C

 'H-NMR (CDC 13, TMS) δ (p pm): 2.07 (3H, s), 6.5-6.7 (2H, m), 6.96 (1H, d, J = 1Hz ), 7.15 (1H, d, J = 8Hz), 7.22 (1H, t, J = 8Hz), 7.30 (1H, d, J = 8Hz), 7.35-7. 41 (1H, m), 7.78 (1H, d, J = 1Hz)

Production Example 8

 5,7-dichroic 6- (2,4,6-trifluorophenyl) imidazo [1,2-a] pyrimidine 0.95 g, 4-fluorophenylboronic acid 0.42 g, potassium phosphate hydrate 1. 91 g, {1,1,1-bis (diphenylphosphino) erocene} dichloropalladium (II) 73 mg of methylene chloride complex and 15 ml of ethylene glycol dimethyl ether are mixed, and mixed at 50 ° C under a nitrogen atmosphere. Heated for hours. Thereafter, the reaction mixture was allowed to cool to room temperature, poured into a 10% aqueous sodium hydroxide solution, and extracted with methyl-tert-butyl ether. The organic layer was washed successively with water, a saturated aqueous solution of sodium chloride and water, dried over anhydrous sodium sulfate and concentrated. The residue was subjected to silica gel column chromatography, washed with methyl tert-butyl ether, and washed with 5- (4-fluorophenyl) -1-61 (2,4,6-trifluorophenylinole) —7-chloroimidazo [1 , 2-a] pyrimidine

 (Hereinafter referred to as the present compound (8).) 0.15 g was obtained.

 Melting point: 188.7 ° C

aH-NMR (CDC 13, TMS) δ (p pm): 6.66 (2H, dd, J = 7.1 Hz, 8.5Hz), 7.16 (2H, t, J = 8.5Hz) , 7.2 1 (1H, d, J = 1.5Hz), 7.35 (2H, dd, J = 5.0Hz, 8.5Hz) 7.79 (1H, d, J = 1.5Hz)

Production Example 9

 5,7-dichroic 6- (2,4,6-trifluorophenyl) imidazo [1,2-a] pyrimidine 0.95 g, 4-ethylpyrroloporonic acid 0.45 g, potassium phosphate water 1.91 g, {1,1, —bis (diphenylphosphino) phenyl} dichloropalladium (II) 73 mg of methylene chloride complex and 30 ml of ethylene dalicol dimethyl ether are mixed at 50 ° C under a nitrogen atmosphere. For 8 hours. Thereafter, the reaction mixture was allowed to cool to room temperature, filtered, and the filtrate was concentrated. After the residue was subjected to silica gel column chromatography, the obtained crude product was mixed with 5 ml of ethyl alcohol and 5 ml of aqueous ammonia, and heated under reflux for 3 hours. The reaction mixture was allowed to cool to room temperature, poured into a 10% aqueous solution of taenoic acid, and extracted with methyl-tert e-butyl ether. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated. The residue was subjected to silica gel column chromatography, and 5- (4-ethylphenyl) -6- (2,4,6-trifluorophenyl) -7 monoimidazo [1,2-a] pyrimidine was obtained.

 (Hereinafter referred to as the present compound (9).) 80 mg was obtained.

 ^ -NM (CDC 13, TMS) δ (ρ pm): 1.25 (3Η, t, J-7.5Hz), 2.68 (2H, q, J = 7.5Hz), 6.6- 6.7 (2 H, m), 7.2.7.3 (5H, m), 7.74 (1H, d, J = 1.5 Hz) Production Example 10

5,7-Dichloro-6- (2,4,6-trifluorophenyl) imidazo [1,2-a] pyrimidine 0.32 g, 4-cyanophenylporonic acid 0.18 g, charcoal 0.42 g of acid lithium, {1,1, —bis (diphenylphosphino) phenoctene} dichloropalladium (II) 24 mg of methylene dichloride salt, molecular sieves 4 A 300 g and ethylene glycol dimethyl ether 10 m 1 And heated at 70 ° C. for 8 hours under a nitrogen atmosphere. After allowing the reaction mixture to cool to room temperature, the mixture was filtered, and the filtrate was poured into a 10% aqueous sodium hydroxide solution, followed by extraction with chloroform. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated. The residue was subjected to silica gel column chromatography, washed with methinolate tert-butyl ether, and 5- (4-cyanophenyl) -16- (2,4,6-trifluorophenyl) —7-cloth imidazo [1 , 2-a] pyrimidine

 (Hereinafter referred to as the present compound (10).) L Omg was obtained.

 ^ -NMR (CDC 13, TMS) δ (ρ pm): 6.68 (2Η, dd, J = 7. OHz, 8.3 Hz), 7.15 (1 H, d, J = 1.2 H z), 7.52 (2H, d, J = 8.4 Hz), 7.79 (2H, d, J = 8.4 Hz), 7.80 (1 H)

Production Example 11

5,7-Dichloro-6- (2,4,6-triphneololophenyl) imidazo [1,2-a] pyrimidine 0.95 g, 0.41 g of 3-methylphenylporonic acid, potassium phosphate hydrate 1.91 g, {1,1,1-bis (diphenylphosphino) phene} dichloropalladium (II) 73 mg of a methylene complex of chloride and ethylene daricol dimethyl ether ₃ Om 1 were mixed under a nitrogen atmosphere. At 50 ° C for 8 hours. Thereafter, the reaction mixture was allowed to cool to room temperature, filtered, and the filtrate was concentrated. After subjecting the residue to silica gel column chromatography, the obtained crude product is mixed with 5 ml of ethyl alcohol and 5 ml of aqueous ammonia, and heated under reflux for 2 hours. did. The reaction mixture was allowed to cool to room temperature, poured into a 10% aqueous solution of taenoic acid, and extracted with methyl tert-butyl ether. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated. The residue was subjected to silica gel gel column chromatography to give 5- (3-methylphenyl) -1-6- (2,4,6-trifluorophenyl) -7-chloroimidazo [1,2-a] pyrimidine

 (Hereinafter referred to as the present compound (11).) 47 mg was obtained.

^X H-NMR (CDC 13, TMS) δ (ρ pm): 2.34 (3Η, s), 6.6-6.7 (2H, m), 7.1—7.4 (5H, m) , 7.76 (1H, s)

Production Example 12

5,7-dichloro-1-6- (2,4,6-trifluorophenyl) imidazo [1,2-a] pyrimidine 0.95 g, 3,4-dimethylmethylphenylpropylonic acid 0.45 g, phosphorus Potassium acid hydrate 1.91 g, {l, 1'-bis (diphenylphosphino) phenecene} Dichroic palladium (II) 73 mg of methylene chloride complex and 40 ml of ethylenedaricol dimethyl ether are mixed under a nitrogen atmosphere. Heated at 50 ° C for 10 hours. Thereafter, the reaction mixture was allowed to cool to room temperature, poured into a 10% aqueous sodium hydroxide solution, and extracted with methyl tert-butyl ether. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated. After the residue was subjected to silica gel column chromatography, the obtained crude product was mixed with 3 ml of ethyl alcohol and 3 ml of aqueous ammonia, and heated under reflux for 1.5 hours. The reaction mixture is concentrated, and the residue is subjected to silica gel column chromatography to give 5- (3,4-dimethylpheninole) -16- (2,4,6-trifluorophenyl) -7-chloroimidazo [1, 2— a] pyrimidine

 (Hereinafter referred to as the present compound (12).) 33 mg was obtained.

^X H-NMR (CDC 13, TMS) δ (ρ pm): 2.28 (3Η, s), 2.29 (3Η, s), 6.63 (2Η, t, J = 8Hz), 7. 03 (1H, d, J = 8Hz), 7.08 (1H, s), 7.16 (1H, d, J = 8Hz), 7.2.7.3 (1H, m), 7 . 74 (1 H, d, J = 1 H z)

Production Example 13

 5,7-Dichloro-6- (2,4,6-trifluoropheninole) imidazo [1,2-a] pyrimidine 0.95 g, 3,4 dimethoxymethylphenylporonic acid 0.55 g, potassium phosphate water 1.91 g, {1,1,1-bis (diphenylphosphino) phenoctene} dichloropalladium (II) 73 mg of methylene dichloride complex and 4 dl of ethylenedaricol dimethyl ether mixed in a nitrogen atmosphere Heated at 50 ° C for 8 hours. Thereafter, the reaction mixture was allowed to cool to room temperature, poured into a 10% aqueous sodium hydroxide solution, and extracted with methyl-tert-butyl ether. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated. The residue is subjected to silica gel column chromatography, washed with a mixture of ethyl acetate and hexane, and 5- (3,4-dimethoxyphenyl) -6- (2,4,6-triphenyl phenyl) _ 7—Chloroimidazo [1, 2-a] pyrimidine

(以下、 本発明化合物 （13) と記す。） 0. 15 gを得た。

(Hereinafter referred to as the present compound (13).) 0.15 g was obtained.

_{^{X H-NM (CDC 1 3}} , TMS) δ (ρ pm): 3. 77 (3Η, s), 3. 91 (3Η, s), 6. 65 (2Η, m), 6. 79 (1Η, d, J = 2Η z), 6.90 (1H, d, J = 8 Hz), 6.94 (1H, dd, J = 2 Hz, 8 Hz), 7.32 (1 H, d, J = lHz), 7.76 (1H, d, J = 1 Hz)

Production Example 14

 5,7-Dichloro-6- (2,6-dichloromouth phenyl) imidazo [1, 2—a

] Pyrimidine

 0.99 g, 0.41 g of 4-methylphenylenoboronic acid, 1.91 g of potassium phosphate hydrate, {1,1'-bis (diphenylphosphino) phene} II) 73 mg of methylene chloride complex and 15 ml of ethylene glycol dimethyl ether were mixed and heated at 60 ° C for 9 hours under a nitrogen atmosphere. Thereafter, the reaction mixture was allowed to cool to room temperature, poured into a 10% aqueous sodium hydroxide solution, and extracted with methyl tert-butyl ether. The organic layer was washed successively with water, a saturated aqueous solution of ammonium chloride and water, dried over anhydrous sodium sulfate and concentrated. The residue was subjected to gel chromatography on a silica gel column, washed with ethyl alcohol, and 5- (4-methylphenyl) -6- (2,6-dichlorophenyl) -7-chloroimidazo [1,2-a ] Pyrimidine

(以下、 本発明化合物 （14) と記す。） 0. 12 gを得た。

(Hereinafter referred to as the present compound (14).) 0.12 g was obtained.

 Melting point: 224.4 ° C

^X H-NMR (CDC 13, TMS) δ (ρ m): 2.36 (3Η, s), 7.18-7.24 (3H, m), 7.27 (1 H, d, J = 1 5 Hz), 7.29-7. 33 (4H, m), 7.76 (1H, d, J-1.5Hz) Production example 15

 5,7-dichloro-6- (2,6-diphnoleo mouth feninole) imidazo [1,2-a] pyrimidine

 0.90 g, 0.41 g of 4-methylphenylboronic acid, 1.91 g of potassium phosphate hydrate, {1,1'-bis (diphenylphosphino) phenyl} dichloro / ク ロ ロ ° radium ( II) 73 mg of methylene chloride complex and 15 ml of ethylene glycol dimethyl ether were mixed and ripened at 60 ° C for 10 hours under a nitrogen atmosphere. Thereafter, the reaction mixture was allowed to cool to room temperature, poured into a 10% aqueous sodium hydroxide solution, and extracted with methyl-tert-butyl ether. The organic layer was washed successively with water, a saturated aqueous solution of ammonium chloride and water, dried over anhydrous sodium sulfate and concentrated. The residue was subjected to silica gel column chromatography, washed with methyl tert-butyl ether, and 5-(4-methylphenyl)-6-(2, 6-difluoro phenyl) 1-7-chloroimidazo [1, 2- a] Pyrimidine

(Hereinafter referred to as the present compound (15).) 0.16 g was obtained. Melting point: 220.2 ° C

 NMR (CDC 13, TMS) δ (ppm): 2.36 (3H, s), 6.86 (2H, m), 7.19-7.25 (4H, m), 7.26 (1H ), 7.30 (1H, m), 7.75 (1H, d, J = 1.5Hz)

Production Example 16

 5,7-dichloro-1- 6_ (2-chloro mouth _ 6-fluorophenyl) imidazo [1, 2, a] pyrimidine

 0.95 g, 0.41 g of 4-methinorefenyl porulonic acid, 1.91 g of potassium phosphate hydrate, {1,1'-bis (diphenylphosphino) phenoctene} dichloropalladium (II) chloride 73 mg of methylene complex and 40 ml of ethylene glycol dimethyl ether were mixed and heated at 60 ° C for 7 hours under a nitrogen atmosphere. Thereafter, the reaction mixture was allowed to cool to room temperature, poured into a 10% aqueous sodium hydroxide solution, and extracted with methyl-tert-butyl ether. The organic layer was washed successively with water, a saturated aqueous solution of ammonium chloride and water, dried over anhydrous sodium sulfate and concentrated. The residue was subjected to silica gel column chromatography, washed with methinolate tert-butyl ether, and 5- (4-methylphenyl) -6- (2-chloro-6-fluorophenyl) -17-chloroimidazo [1,2 — A] Pyrimidine

 (Hereinafter referred to as the present compound (16).) 04 g was obtained.

Melting point: 230. 9 ° C NMR (CDC 1a, TMS) δ (p pm): 2.36 (3H, s), 6.96 (1H, dt, J = 1.0 Hz, 8.3Hz), 7.18-7. 26 (4 H, m), 7.20 (1H), 7.26—7.30 (2H, m), 7.75 (1 H, d, J = 1.5 Hz)

6 (2,4-difluorophenyl) imidazo [1, 2—

0.90 g, 4-methylphenylporonic acid 0.41 g, potassium phosphate hydrate 1.91 g, {1,1,1-bis (diphenylphosphino) phenol} dichloropalladium (II) chloride 73 mg of methylene complex and 40 ml of ethylenedaricol dimethyl ester were mixed and heated at 60 ° C for 7 hours under a nitrogen atmosphere. Thereafter, the reaction mixture was allowed to cool to room temperature, then poured into a 10% aqueous sodium hydroxide solution, and extracted with methyl tert-butyl ether. The organic layer was washed successively with water, a saturated aqueous solution of ammonium chloride and water, dried over anhydrous sodium sulfate and concentrated. After the residue was subjected to silica gel column chromatography, the obtained crude product was mixed with 5 ml of ethanolic ethanol and 5 ml of aqueous ammonia, and heated under reflux for 3 hours. The reaction mixture was allowed to cool to room temperature, poured into a 10% aqueous solution of citric acid, and extracted with methyl tert-butyl ether. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated. The residue was subjected to silica gel column chromatography, and 5- (4-methynolepheninole) -6- (2,4-diphenololenophenyl) -1-7-chloroimidazo [1,2-a] pyrimidine 02014

80

 (Hereinafter referred to as the present compound (17).) 0.1 g was obtained.

 Melting point: 164.5 ° C

Ichikaku _{R (CDC 1 3, TMS)} δ (pm): 2. 37 (3H, s), 6. 76- 6. 83 (2H, m), 7. 03- 7. 09 (4H, m), 7.25 (1 H), 7.74 (1H, d, J = 1.5 Hz)

Production Example 18

 5,7-dichloro-1-6- (2-fluorophenyl) imidazo [1,2-a] pyrimidine

0.85 g, 0.41 g of 4-methylphenylporonic acid, 1.91 g of potassium phosphate hydrate, {1,1, —bis (dipheninolephosphino) phenol} dichloropalladium (II ) 73 mg of methylene chloride complex and 40 ml of ethylene glycol dimethyl ether were mixed and heated at 60 ° C for 6 hours under a nitrogen atmosphere. Thereafter, the reaction mixture was allowed to cool to room temperature, poured into a 10% aqueous sodium hydroxide solution, and extracted with methyl tert-butyl ether. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated. After the residue was subjected to silica gel gel chromatography, the obtained crude product was mixed with 10 ml of ethyl alcohol and 5 ml of aqueous ammonia, and heated under reflux for 6 hours. The reaction mixture was allowed to cool to room temperature, poured into a 10% aqueous solution of citric acid, and extracted with methyl-tert-butyl ether. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated. Residue is methyl-tert -Wash with butyl ether, and 5-(4-methylphenyl)-6-(2-fluorophenyl) 1 7-chloroimidazo [1, 2-a] pyrimidine

 (Hereinafter referred to as the present compound (18).) 0.15 g was obtained.

 Melting point: 188.6 ° C

 ^ -NM (CDC 1 TMS) δ (p pm): 2.35 (3H, s), 7.00-7.09 (3H, m), 7.18 (4H, s), 7.25 (1H , s), 7.27-7. 31 (1H, m), 7.74 (1H, s)

Production Example 19

 5,7-Dichrolic 6- (2-Chlorophenyl) imidazo [1,2-a] pyrimidine

0.90 g, 0.41 g of 4-methylphenylboronic acid, 1.91 g of potassium phosphate hydrate, {1,1,1-bis (dipheninolephosfuino) fuecsen} 73 mg of dimethylene (II) methylene chloride complex and 40 ml of ethylene glycol dimethyl ether were mixed and heated at 50 ° C for 6 hours under a nitrogen atmosphere. Thereafter, the reaction mixture was allowed to cool to room temperature, poured into a 10% aqueous sodium hydroxide solution, and extracted with methyl tert-butyl ether. The organic layer was washed successively with water and a saturated aqueous solution of ammonium chloride, dried over anhydrous sodium sulfate and concentrated. After the residue was subjected to silica gel column chromatography, the obtained crude product was mixed with 10 ml of ethyl alcohol and 5 ml of aqueous ammonia, and heated under reflux for 18 hours. reaction The mixture was allowed to cool to room temperature, poured into a 10% aqueous solution of citric acid, and extracted with methyl-tert-butyl ether. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated. The residue was subjected to silica gel column chromatography, washed with methyl tert-butyl ether, and then washed with 5- (4-methylphenyl) 16- (2-chlorophenol) _7-cycloimidazo [1, 2 -a] pyrimidine

 (Hereinafter referred to as the present compound (19).) 0.10 g was obtained.

 Melting point: 211.5 ° C

^J H-NMR (CDC 13, TMS) δ (p pm): 2.34 (3H, s), 7.09 (1H, dd, J = 2Hz, 8Hz), 7.17 (1H, t, J = 8Hz), 7.15-7.25 (4H, m), 7.26 (1H, dt, J = 2Hz, 8Hz), 7.26 (1H), 7.38 (1H, d, J = 8Hz), 7.74 (1H, d, J = 1Hz)

(2,4 dicro-mouth feninole) imidazo [1, 2-a

1. 32 g, 0.54 g of 4-methylphenylboronic acid, 2.53 g of potassium phosphate hydrate, {1,1, —bis (diphenylphosphino) phenoctene) dichloropalladium (II ) 97 mg of methylene chloride complex and 50 ml of ethylene glycol dimethyl ether were mixed and heated at 50 ° C for 8 hours under a nitrogen atmosphere. Then, anti The reaction mixture was allowed to cool to room temperature, filtered, and the filtrate was concentrated. The residue was subjected to silica gel column chromatography, washed with ethyl alcohol, and 5-(4-methylinolephenyl)-6-(2,4- dichloromouth feninole)-17-chloroimidazo [1,2- a] Pyrimidine

 (Hereinafter referred to as the present compound (20).) 95 mg was obtained.

One _{NMR (CDC 1 3, TMS)} δ (p pm):. 2. 37 (3H, s), 7. 03 (. 1H, d, J = 8 1H z), 7. 1-7 3 (6H, m), 7.41 (1 H, d, J = 2.OHz), 7.75 (1 H, d, J = 1.7 Hz) Production Example 21

 8 Omg of sodium hydride (60% oily) was suspended in 5 ml of tetrahydrofuran, and a solution of 0.32 g of getyl malonate in tetrahydrofuran and a solution of 0.37 g of the compound of the present invention (1) in tetrahydrofuran were sequentially added dropwise at room temperature. After that, it was heated at 50 for 20 hours. After allowing the reaction mixture to cool to room temperature, the mixture was poured into a 10% aqueous solution of citric acid, and extracted with methinolate tert_butyl ether. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated. The residue was subjected to silica gel column chromatography, and [5- (4-methylphenyl) -6- (2,4,6-trifluorophenyl) imidazo [1,2-a] pyrimidine-17-yl] malonic acid Jethil

0. 21 gを得た。

0.21 g was obtained.

 iH—NMR (CDC 1 a, TMS) δ (p pm): 1.24 (6H, t,

J = 7.1 Hz), 2.37 (3H, s), 4.1—4.3 (4H, m), 4.75 (1H, s), 6.62 (2H, dd, J = 7. 1 Hz, 8.6 Hz), 7.20 (4H, s), 7.25 (1H, d, J = 1.4 Hz), 7.77 (1H, d, J

= 1. 4Hz)

 [5-(4-Methinolepheninole)]-6-(2,4,6-Triphnoleolopheninole) Imidazo [1,2-a] pyrimidin-1 7-yl] Jetyl malonate 0.20 g And 5 ml of concentrated hydrochloric acid, and heated at 80 ° C. for 1 hour. The reaction mixture was allowed to cool to room temperature, poured into a 10% aqueous sodium hydroxide solution, and extracted with methyl-tert-butyl ether. The organic layer was washed with water, dried over anhydrous sodium sulfate, and then concentrated. The residue was subjected to silica gel chromatography to give 5- (4-methylphenyl) -6- (2,4,6-trifluorophenyl) -1-methinoleimidazo [1,2-a] pyrimidine

 (Hereinafter referred to as the present compound (21).) 0.12 g was obtained.

 Melting point: 186.5 ° C

 H—NMR (CDC 13, TMS) δ (ρ pm): 2.37 (3Η, s), 2.43 (3H, s), 6.63 (2H, m), 7.16 (1 H, s) ), 7.19 (4 H, m), 7.69 (1H, s)

Production Example 22

0.16 g of sodium hydride (60% oil) was suspended in 2 ml of tetrahydrofuran, and a solution of 0.64 g of getyl malonate in tetrahydrofuran and a solution of 0.35 g of the compound (19) of the present invention in tetrahydrofuran were sequentially added dropwise at room temperature. After 9 o'clock The mixture was refluxed while heating. The reaction mixture was allowed to cool to room temperature, poured into a 10% aqueous solution of citric acid, and extracted with methyl-tert-butyl ether. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated. The residue was applied to a silica gel column chromatography, and [5- (4-methylphenyl) -6- (2-chlorophenol) imidazo [1,2-a] pyrimidine-1 7-yl] malonic acid Jethil

 0.37 g was obtained.

 Melting point: 127.3 ° C

One _{NMR (CDC 1 3, TMS)} δ (p pm): 1. 13 (3H, t, J = 7. 2H z), 1. 30 (. 3H, t, J = 7 2H z), 2. 33 (3H, s), 4.0—4.1 (2H, m), 4.2.4.4 (2H, m), 4.71 (1 H, s), 7.07 (1 H, dd , J = 1.7 Hz, 7.6 Hz), 7.1-7.3 (7H, m), 7.38 (1H, dd, J = 0.7 Hz, 8.0 Hz), 7.76 (1 (H, d, J = 1.4Hz)

[5 -— (4-methylphenyl) _6— (2-chlorophenyl) imidazo [1,2-a] pyrimidine—7-yl] Mix 0.26 g of getyl malonate and 2 ml of concentrated hydrochloric acid, and add 0. The mixture was refluxed for 5 hours. The reaction mixture was allowed to cool to room temperature, poured into a 10% aqueous sodium hydroxide solution, and extracted with chloroform. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated. The residue was subjected to silica gel gel chromatography, and 5- (4-methylphenyl) -16- (2-chlorophenyl) -17-methylimidazo [1,2-a] pyrimidine

 (Hereinafter referred to as the present compound (22).) 0.15 g was obtained.

 Melting point: 229.9 ° C

 ^ I-NMR (CDC 13, TMS) δ (ppm): 2.33 (3H, s), 2.38 (3H, s), 7.06 (1 H, dd, J = 1.6 Hz, 7 6Hz), 7.10-7.26 (7H, m), 7.39 (1H, dd, J = 1.2Hz, 8.OHz), 7.69 (1H, d, J = 1.5H z)

Production Example 23

 0.12 g of the present compound (1), 39 mg of potassium cyanide, 60.15 g of dibenzo-18-one crown-1 and 0.15 g of N, N-dimethylformamide were mixed and heated at 100 for 3 hours. . Water was poured into the reaction mixture at room temperature, and the mixture was extracted with methyl-tert-butyl ether. The organic layer was washed sequentially with 10% sodium hydroxide and water, dried over anhydrous sodium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to give 5- (4-methinolephenyl) -6- (2,4,6-triphneoleolophenyl) -1-cyanoimidazo [1,2-a] pyrimidine

 (Hereinafter referred to as the present compound (23).) 58 mg was obtained.

 Melting point: 205.2 ° C

One _{NMR (CDC 1 3, TMS)} δ (P m): 2. 1 (3H, s), 6.70 (2H, dd, 1 = 7.lHz, 8.6Hz), 7.20-7.29 (4H, m), 7.54 (1H, d, J = 1.5Hz), 8.06 (1H, d, J = 1.5Hz)

Production Example 24

 0.17 g of the present compound (1), 0.13 g of sodium methoxide (28% methanol solution) and 2 ml of methanol were mixed at room temperature. After standing overnight, water was poured into the reaction mixture, which was extracted with black hole form. The organic layer is washed with water, dried over anhydrous sodium sulfate, concentrated, and concentrated to 5- (4-methylphenyl) -1-6- (2,4,6-trifluorophenyl) -17-methoxyimidazo [1,2- a] pyrimidine

 (Hereinafter, this is referred to as the present compound (24).) 0.15 g was obtained.

 Melting point: 231.8 ° C

 iH—NMR (CDC 13, TMS) δ (p pm): 2.37 (3H, s), 4.04 (3H, s), 6.58 (2H, dd, J = 7.lHz , 8.6Hz): 7.06 (1H, d, J = 1.7), 7.20 (4H, s), 7.47 (1H, d, J-1.7Hz) The production method of the intermediate for producing the invention compound is described as a reference production example.

Reference Production Example 1

HN ^

 N HCI

H ₂ N

 Sodium hydride (60% oil-based) 4.8 was suspended in 1,4-dioxane 10 Om 1, and 19.2 g of getyl malonate was added dropwise at room temperature. Thereafter, 17.2 g of copper (I) bromide and 21.1 g of 1-bromo-1,2,4,6-trifluorobenzene were sequentially added to the mixture at 40 ° C., and the mixture was heated under reflux for 26 hours. Thereafter, the reaction mixture was ice-cooled, concentrated hydrochloric acid was added to the reaction mixture, and liquid separation was performed with tert_butyl methyl ether and water. The organic layer was washed sequentially with an aqueous sodium hydroxide solution, diluted hydrochloric acid, and water, dried over anhydrous sodium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 12.6 g of getyl (2,4,6-trifluorophenyl) malonate.

^J H-NMR (CDC 13, TMS) δ (p pm): 1.28 (6H, t, J = 7.1 Hz), 4.26 (4H, q, J = 7.1 Hz), 4 89 (1H, s), 6.71 (2H, t, J = 8.2Hz)

(2,4,6-trinoleolophenyl) getyl malonate 2.9 g, 2.39 g of 2-aminoaminoimidazole hydrochloride, DBU 4.57 g, N, N-dimethylformamide 1 Om 1 Was stirred at 100 ° C. for 6 hours. Thereafter, the reaction mixture was allowed to cool to room temperature, and the reaction mixture was added with chloroform and extracted twice with water. The aqueous layers were combined and concentrated. 1 Om 1 of water was added to the obtained residue. Concentrated hydrochloric acid was added to the solution under ice cooling. The precipitated precipitate is collected by filtration, dried and dried with 5,7-dihydroxy-6- (2,4,6-trifluoromethyl) imidazo [1,2-a] pyrimidine 2.2 g was obtained.

^ -NMR (DMSO-d ₆ , TMS) δ (p pm): 7.11 (2H, dd, J = 7.7 Hz, 9.2 Hz), 7.39 (1H, d, J = 2 .5Hz), 7.48 (1H, d, J = 2.5Hz), 11.9 (2H, brs)

 A mixture of 2.1 g of 5,7-dihydroxy-6- (2,4,6-trifluorophenyl) imidazo [1,2-a] pyrimidine and 5 ml of phosphorus oxychloride was heated under reflux for 24 hours. Thereafter, the reaction mixture was concentrated. The residue was dissolved in a small amount of dichloromethane, and a saturated aqueous solution of sodium hydrogen carbonate was added to the solution. This was extracted with dichloromethane. The organic layer was washed successively with a saturated aqueous solution of sodium hydrogencarbonate and saturated saline, dried over anhydrous sodium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 1.39 g of 5,7-dichloro-1- (2-, 4,6-trifluorophenyl) imidazo [1,2-a] pyrimidine.

 Melting point: 192.5 ° C

One _{NMR (CDC 1 3, TMS)} δ (ppm): 6. 88 (2H, dd, J = 8. 6H z, 7. lHz), 7. 75 (1 H, d, J = 1H z), 7 . 92

(1H, d, J = lHz)

Reference Production Example 2

Sodium hydride (60% oil-based) 5.68 was suspended in 1,4-dioxane (70 ml), and 22.4 g of getyl malonate was added dropwise at 60 ° C. After that, this mixture At 60 ° C., 10.2 g of copper (I) bromide and 15.8 g of benzene having 1-bromo_2,6-dichlorobenzene were sequentially added, and the mixture was refluxed for 21 hours. Thereafter, the reaction mixture was ice-cooled, concentrated hydrochloric acid was added to the reaction mixture, and liquid separation was performed with methyl tert-butyl ether and water. The organic layer was washed sequentially with dilute hydrochloric acid and water, dried over anhydrous sodium sulfate, and concentrated. The residue was distilled under reduced pressure to obtain 7.59 g of (2,6-dichrophenyl) methyl getyl.

 Boiling point: 130-144 ° C (0.14mmHg)

^X H-NM (CDC 13, TMS) δ (p pm): 1.28 (6H, t, J = 7.1 Hz), 4.26 (4H, q, J = 7.1 Hz), 5.44 (1H, s), 7.18-7.23 (1H, m), 7.35 (2H, q, J = 7.8Hz)

(2,6-Dichloromouth phenyl) 7.32 g of getyl malonate, 3.81 g of 2-aminoimidazole sulfate, 8.04 g of DBU and 15 ml of N, N-dimethylformamide at 100 ° C Stirred for 6 hours. Thereafter, 20 ml of water was added to the reaction mixture, and the mixture was allowed to cool to room temperature. The resulting precipitate was collected by filtration and dried to give 5.17 g of 5,7-dihydroxy-1-6- (2,6-dichlorophenyl) imidazo [1,2-a] pyrimidine * DBU salt.

^X H-NMR (DMSO-d ₆ , TMS) δ (p pm): 1.59—1.6

7 (6H, m), 1.87-1.94 (2H, m), 2.49-2.51 (2H, m), 3.23 (2H, t, J = 5.6Hz), 3 46 (2H, t, J = 5.7 Hz), 3.52-3.56 (2H, m), 6.69 (1 H, d, J = 1.5 Hz), 7.09 (1H, d, J = 1.5 Hz, 7.15-7.20 (1H, m), 7.35 (2H, d, J = 8.OHz), 9.5 (brs), 10.3 (brs )

5,7-Dihydroxy 6- (2,6-dichlorophenyl) imidazo [1,2-1a] pyrimidine ′ DBU salt 4.48 g of a mixture of phosphorus oxychloride 2 Om 1 was heated to reflux for 16 hours. Thereafter, the reaction mixture was allowed to cool to room temperature and concentrated. The residue was dissolved in a small amount of chloroform, and a saturated aqueous solution of sodium hydrogen carbonate was added to the solution. This was extracted with chloroform. The organic layer was washed successively with a saturated aqueous solution of sodium hydrogen carbonate and water, dried over anhydrous sodium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to give 5,7-dichloro-6_ (2, 6- 2.64 g of dichlorophenyl) imidazo [1,2-a] pyrimidine were obtained.

^X H-NMR (CDC 13, TMS) δ (ρ pm): 7.41—7.46 (1Η, m), 7.50-7.53 (2Η, m), 7.76 (1H, d , J = 1.5 Hz), 7.92 (1H, d, J = 1.4 Hz)

Reference Production Example 3

ΗΝ ^ Ϊ

N 1 / 2H ₂ S0 ₄

H ₂ N

Sodium hydride (60% oil) 8.00 _§ and 10 Oml of 1,4-dioxane (10 Oml) were added dropwise with 32.0 g of getinole maltate at 60 ° C, followed by copper (I) bromide (14). .6 g and 1-bromo-2,6-difluorobenzene were sequentially added, and the mixture was heated under reflux for 16 hours. After adding concentrated hydrochloric acid to the reaction mixture under ice cooling, tert-butyl methyl ether and water were added, and the mixture was separated. The organic layer was washed sequentially with dilute hydrochloric acid and water, dried over sodium sulfate, and concentrated. The residue was distilled under reduced pressure to obtain 16.5 g of (2,6-difluorophenol) malonate getyl.

Boiling point: 107 ^D C_109 ° C (0.14 mmH g)

 XH-NM (CDC 13, TMS) δ (p pm): 1.28 (6H, t,

J = 7.1Hz), 4.26 (4H, q, J = 7.1Hz), 4.96 (1H, s), 6.93 (2H, m), 7.30 (1H, m)

(2,6-Difluorophenyl) maltonic acid jetinole 13.6 g, 2-aminoimidazole sulfate 7.93 g, DBU9.13 N-dimethylformamide 30 m 1 mixture at 100 ° C For 7 hours. Water is added to the reaction mixture, After allowing to cool to room temperature, the mixture was separated with t-butyl methyl ether. Concentrated hydrochloric acid was added to the aqueous layer, and the deposited precipitate was collected by filtration and dried to obtain 7,84 g of 5,7-dihydroxy-16- (2,6-difluorophenyl) imidazo [1,2-a] pyrimidine. Was.

NMR (DMSO—d ₆ , TMS) δ (p pm): 7.05 (2H, t, J = 8 Hz), 7.3-7.4 (1H, m), 7.40 (1H, d, J = 2Hz), 7.49 (1H, d, J = 2Hz), 11.94 (2H, brs)

 5, 7-dihydroxy-6- (2,6-diphneololophenyl) imidazo [1,2-a] pyrimidine 7.63 g, DBU 4.85 g and a mixture of oxysulfonated phosphorus 29 ml were refluxed. Heated under the conditions for 10 hours. After the reaction mixture was concentrated, chloroform and a saturated aqueous solution of sodium hydrogen carbonate were added to the residue, and the mixture was separated. The organic layer was washed successively with a saturated aqueous solution of sodium hydrogencarbonate and a saturated saline solution, dried over sodium sulfate, and concentrated. The residue was subjected to silica gel gel chromatography to obtain 2.48 g of 5,7-dichloro-6- (2,6-difluorophenyl) imidazo [1,2-a] pyrimidine.

¹ H-NMR (CDC 13, TMS) δ (ppm): 7.09 (2H, dd, J = 7.5 Hz, 8.2 Hz), 7.5-7.6 (1H, m), 7 74 (1 H, d, J = 1.7 Hz), 7.90 (1 H, d, J = 1.2 Hz)

Reference Production Example 4

产 N 1/2H₂SO₄

产 N 1 / 2H ₂ SO ₄

 H Ku N

水素化ナトリウム （60%油性） 7. 2 gと炭酸ジェチル 17. 0 gとテトラ ヒドロフラン 150mlとの混合物に、 還流条件下に、 2_クロロー 6—フルォ 口フエニル酢酸ェチル 26. 0 gを滴下し、 8時間還流条件下に加熱した。 反応 混合物を放冷後、 氷冷した希塩酸へ注カ卩し、 t -プチルメチルエーテルで抽出し た。 有機層を水洗し、 硫酸ナトリウムで乾燥した後、 濃縮した。 残渣をシリカゲ ルク口マトグラフィ一に付し、 (2—クロロー 6—フノレオロフェニル） マロン酸ジ ェチル 30. 4 gを得た。

To a mixture of 7.2 g of sodium hydride (60% oil), 17.0 g of getyl carbonate, and 150 ml of tetrahydrofuran, 26.0 g of 2-chloro-6-fluoroethyl phenylacetate was added dropwise under reflux conditions. Heated under reflux conditions for 8 hours. After allowing the reaction mixture to cool, the mixture was poured into ice-cooled diluted hydrochloric acid and extracted with t-butyl methyl ether. The organic layer was washed with water, dried over sodium sulfate, and concentrated. The residue was subjected to silica gel mouth chromatography to obtain 30.4 g of diethyl (2-chloro-6-funolelophenyl) malonate.

¹ H-NMR (CDC 1 a, TMS) δ (ppm): 1.28 (6H, t, J = 7.1 Hz), 4.26 (4H, q, J = 7.1 Hz), 5. 16 (1H, s), 7.0-7.1 (1H, m), 7.2-7.4 (2H, m)

 (2-Chloro-6-Fluorofeninole) 2.89 g of getyl germate and amino imidazole hydrochloride 1.20 and 1,5-diazabicyclo [4,3,0] —5-Nonene (DBN ) A mixture of 2.48 g and 10 ml of N, N-dimethylformamide (DMF) was heated at 100 ° C for 4 hours. After allowing the reaction mixture to cool, the precipitated precipitate was filtered and dried, and 5,7-dihydroxy-6- (2-chloro-6_fluorophenyl) imidazo [1,2-a] pyrimidine · DBN salt 1.80 g was obtained.

¹ H-NMR (DMSO—d ₆ , TMS) δ (pm): 1.8—1.9 (2 H, m), 1.9-2.0 (2H, m), 2.76 (2H, t, J = 7.9 Hz), 3.27 (2H, t, J = 5.7), 3.35 (2H, t, J = 5.7Hz), 3.58 (2H, t, J = 7.2Hz), 6.69 (1H, d, J = 1.6Hz), 7.0-7.1 (1H, m), 7.07 (1H, d, J = l.6Hz ), 7.1-7. 2 (2H, m), 10.35 (2H, brs)

5,7-Dihydroxy 6- (2-chloro-6-funolelopheninole) imidazo [1,2-a] pyrimidine 'DBN salt 1.62 g and a mixture of oxy-salt iridine 5 ml 1 Heated under reflux conditions for 10 hours. The reaction mixture was concentrated. Dichloromethane and saturated aqueous sodium hydrogen carbonate solution were added to the residue, and the mixture was separated. The organic layer was washed successively with a saturated aqueous solution of sodium hydrogen carbonate and water, dried over sodium sulfate, and concentrated. The residue was subjected to silica gel chromatography to give 5,7-dichroic port _ 6- (2-chloro-6-fluorophenyl) imita, zo [1,2-a] pyrimidine 1.0 0 g was obtained.

¹ H-NMR (CDC 13, TMS) δ (p pm): 7.1-7.2 (1 H, m), 7.4-7.6 (2H, m), 7.76 (1 H, d, J = lHz), 7.92 (1H, d, J = 1Hz)

Reference Production Example 5

N 1 / 2H ₂ SO ₄

H ₂ N

 Sodium hydride (60% oil-based) To a mixture of 8.008 and 1,4-dioxane (100 ml) at 60 ° C was dropped 32.0 g of getyl germate, followed by copper (I) bromide (14.6). g and 19.3 g of 1-bromo-2,4-difluorobenzene were sequentially calorimetrically heated and refluxed for 20 hours. After adding concentrated hydrochloric acid to the reaction mixture under ice cooling, t-tert-butyl methyl ether and water were added, and the mixture was separated. The organic layer was washed sequentially with dilute hydrochloric acid and water, dried over sodium sulfate, and concentrated. The residue was distilled under reduced pressure to obtain 12.5 g of getyl (2,6-difluorophenyl) malonate.

 Boiling point: 107 ° C — 113 ° C (0.2 mm Hg)

_{1 H-NMR (CDC 1 3} , TMS) δ (p pm): 1. 2- 1. 3 (6

H, m), 4.2.4.3 (4H, m), 4.92 (1H, s), 6.84 (1H, m), 6.91 (1H, m), 7.4 7.6 (1 H, m)

(2,4-Difluorophenyl) maltonic acid jetinole (12.0 g), 2-aminoimidazole sulfate (6.99 g), DBU (14.8 g) and N, N-dimethylformamide (26 ml) in 100 Heated for hours. Water is added to the reaction mixture, After allowing to cool to room temperature, liquid separation was performed with t-butyl methyl ether. Concentrated hydrochloric acid was added to the aqueous layer, and the deposited precipitate was collected by filtration and dried to obtain 5.80 g of 5,7-dihydroxy-16- (2,4-difluorophenyl) imidazo [1,2-a] pyrimidine. Was.

¹ H-NMR (DMSO—d ₆ , TMS) 8 (p pm): 7.04 (1 H, dt, J = 2.4 Hz, 8.5 Hz), 7.16 (1H, dt, J = 2 6H z, 9.7Hz), 7.34 (1H, dt, 1 = 7.0Hz, 8.5H z), 7.40 (1H, d, J = 2.4Hz,) 7.49 (1H, d, J = 2.41- I z)

 5,7-dihydroxy_6— (2,4 diphneololopheninole) imidazo [1,2-a] pyrimidine 5.80 g, 3.68 g of DBU and 22 m 1 of oxysulfonated phosphorus, Heated under reflux conditions for 7 hours. After concentrating the reaction mixture, the reaction mixture was separated by adding porcelain form and a saturated aqueous solution of sodium hydrogen carbonate. The organic layer was washed successively with a saturated aqueous sodium hydrogen carbonate solution and a saturated saline solution, dried over sodium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 1.82 g of 5,7-dichloro-6- (2,4-difluorophenyl) imidazo [1,2-a] pyrimidine.

_{^{1 H-NMR (CDC 1 3}} , TMS) δ (p pm): 6. 9- 7. 1 (2

H, m), 7.2-7.3 (1H, m), 7.73 (1H, d, J = 15 Hz), 7.90 (1 H, d, J = 1.5 Hz)

Reference Production Example 6

水素化ナトリウム （60%油性） 11. 2 §と 1, 4—ジォキサン 14 Oml との混合物に、 60 °Cでマ口ン酸ジェチル 44. 8 gを滴下した後、 臭化鲖 （ I ) 20. 4 gと 2—ブロモフルォロベンゼン 24. 5 gとを順次加え、 22時間 加熱還流した。 反応混合物に氷冷下濃塩酸を加えた後、 t e r t一ブチルメチル エーテルと水とを加え、 分液した。 有機層を希塩酸、 10%水酸ィ匕ナトリウム水 溶液、 希塩酸、 水で順次洗浄し、 硫酸ナトリウムで乾燥した後、 濃縮した。 残渣 をシリカゲルクロマトグラフィ一に付し、 (2—フルオロフェ -ル） マロン酸ジェ チル 17. 6 gを得た。

Sodium hydride (60% oil) 11.2 § and 1,4-dioxane 14 Oml were added dropwise at 60 ° C with 44.8 g of getyl germate, and then bromide (I) 20 .4 g and 24.5 g of 2-bromofluorobenzene were sequentially added, and the mixture was heated under reflux for 22 hours. After adding concentrated hydrochloric acid to the reaction mixture under ice-cooling, tert-butyl methyl ether and water were added, and the mixture was separated. The organic layer was washed sequentially with diluted hydrochloric acid, a 10% aqueous sodium hydroxide solution, diluted hydrochloric acid, and water, dried over sodium sulfate, and concentrated. The residue was subjected to silica gel chromatography to obtain 17.6 g of ethyl (2-fluorophenyl) malonate.

¹ H-NMR (CDC 13, TMS) δ (p pm): 1.27 (6H, m), 4.2-4.3 (4H, m), 4.97 (1H, s), 7.08 (1H, m), 7.16 (1 H, m), 7.3-7.4 (1 H, m), 7.47 (1H, m)

 A mixture of 17.1 g of getyl (2-fluorophenyl) malonate, 10.6 g of 2-aminoimidazole sulfate, 22.4 g of DBU and 40 ml of N, N-dimethylformamide was heated at 100 ° C for 8 hours. . Water was added to the reaction mixture, the mixture was allowed to cool to room temperature, and then separated with t-butyl methyl ether. Concentrated hydrochloric acid was added to the aqueous layer, and the deposited precipitate was collected by filtration and dried to obtain 5.3 g of 5,7-dihydroxy-6- (2-fluorophenyl) imidazo [1,2-a] pyrimidine.

¹ H-NMR (DMSO-d ₆ , TMS) δ (p pm): 7.1-7.2 (2H, m), 7.2-7.4 (2H, m), 7.39 (1H, d, J = 2.7 Hz), 7.50 (1H, d, J = 2.4 Hz), 12.6 (brs)

 5,7-Dihydroxy-1- (2-fluorophenyl) imidazo [1,2-a] pyrimidine 7.36 g, DBU5.02 g and a mixture of Oxy-Shi-Dai-Rin 30m 1 were refluxed for 11 hours. Heated. After the reaction mixture was concentrated, chloroform and a saturated aqueous sodium hydrogen carbonate solution were added to the residue, and the layers were separated. The organic layer was washed successively with a saturated aqueous solution of sodium hydrogen carbonate and a saturated saline solution, dried over sodium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 1.70 g of 5,7-dichloromethane-6- (2-fluorophenyl) imidazo [1,2-a] pyrimidine.

¹ H-NMR (CDC 13, TMS) δ (P pm): 7.2-7.3 (1 H, m), 7.3-7.4 (2H, m), 7.5-7.6 (1H, m), 7.73 (1H, d, J = 1.4 Hz), 7.89 ( 1H, d, J = l. 5H z)

Reference Production Example 7

N 1 / 2H ₂ S0 ₄

H ₂ N

 To a mixture of 12.0 g of sodium hydride (60% oil-based) and 15 Oml of 1,4-dioxane was added dropwise 48.1 g of getyl macrate at 60 ° C, followed by copper (I) bromide (21). 9 g and 28.7 g of 2-bromochlorobenzene were mixed around 1 hour and heated to reflux for 18 hours. After adding concentrated hydrochloric acid to the reaction mixture under ice-cooling, t-tert-butylmethyl ether and water were added, and the mixture was separated. The organic layer was washed successively with diluted hydrochloric acid, a 10% aqueous solution of sodium hydroxide, diluted hydrochloric acid, and water, dried over sodium sulfate, and concentrated. The residue was subjected to gel chromatography on a gel with a gel force to obtain 24.3 g of (2-chloro-mouth feninole) maltinate.

¹ H-NMR (CDC 13, TMS) δ (p pm): 1.28 (6H, t, J = 7.1Ηζ), 4.25 (4H, m), 5.21 (1H, s), 7 2—7.3 (2H, m), 7.3-7.4 (1H, m), 7.4.7.5 (1H, m)

A mixture of 17.1 g of getyl malonate, 10 g of 2-aminoimidazole sulfate, DBU21.lg and 40 ml of N, N-dimethylformamide was heated at 100 ° C. for 10 hours. Water was added to the reaction mixture, the mixture was allowed to cool to room temperature, and then separated with t-butyl methyl ether. Concentrated hydrochloric acid was added to the aqueous layer, and the deposited precipitate was collected by filtration, dried, and dried with 5,7-dihydroxy-6- (2-chlorophenyl). Imidazo [1,2-a] pyrimidine 12. lg was obtained.

¹ H-NMR (DMSO-d ₆ , TMS) δ (p pm): 7.2-7.3 (3H, m), 7.38 (1H, d, J = 2.6 Hz), 7.4 7.5 (1H, m), 7.49 (1H, d, J = 2.4 Hz), 12.5 (brs)

 5, 7-dihydroxy 6- (2-chloro phenyl) imidazo [1, 2-a] pyrimidine 6.54 g, DBU 4.12 g Heated under reflux conditions for 4 hours. After concentrating the reaction mixture, chloroform and a saturated aqueous sodium hydrogen carbonate solution were added to the residue, and the layers were separated. The organic layer was washed with water, dried over sodium sulfate, and concentrated. The residue was washed with ethylene daricol dimethyl ether to obtain 5.87 g of 5,7-dichloro-6- (2-chloropheninole) imidazo [1,2-a] pyrimidine.

¹ H-NMR (CDC 13, TMS) δ (p pm): 7.32 (1H, dd, J = 1.7 Hz, 7.6 Hz), 7.4-7.5 (2H, m), 7 58 (1 H, dd, J = 1.3 Hz, 7.9 Hz), 7.73 (1H, d, J = 1.5 Hz), 7.90 (1H, d, J = 1.7 Hz)

 Reference Production Example 8

To a mixture of sodium hydride (60% oily) 10.0 and 130 ml of 1,4-dioxane at 60 ° C was added dropwise 40.0 g of getyl macrate, followed by copper (I) bromide 18.2 g and 1-bromo-2,4-dichloromouth benzene 25.O g The mixture was heated under reflux for 17 hours. After adding concentrated hydrochloric acid to the reaction mixture under ice cooling, tert-butyl methyl ether and water were added, and the mixture was separated. The organic layer was washed sequentially with diluted hydrochloric acid, a 1.0% aqueous sodium hydroxide solution, diluted hydrochloric acid, and water, dried over sodium sulfate, and concentrated. The residue was subjected to gel chromatography on a silica gel to obtain 28.4 g of getyl (2,4-dichlorophenyl) malonate.

¹ H-NMR (CDC 13, TMS) 8 (p pm): 1.2—1.3 (6 H, m), 4.2—4.4 (4H, m), 5.15 (1H, s ), 7.2.7.3 (1H, m), 7.4.7.5 (2H, m)

 (2,4-Dichlorophenyl) 9.62 g of getyl malonate, 5.0 g of 2-aminoimidazole sulfate, 10.5 g of DBU and 25 ml of N, N-dimethylformamide at 100 ° C Heated for 10 hours. Water was added to the reaction mixture, the mixture was allowed to cool to room temperature, and then separated with t-butyl methyl ether. Concentrated hydrochloric acid was added to the aqueous layer, and the resulting precipitate was filtered and dried to obtain 5,7-dihydroxy-6_ (2,4-dichlorophenyl) imidazo [1,2-a] pyrimidine (7.0 g). .

1 H-NMR (DMSO-d ₆ , TMS) δ (p pm): 7.31 (1H, d, J = 8.3 Hz), 7.35-7.40 (2H, m), 7. 48 (11-1, d, J = 3.5 Hz), 7.58 (1 H, d, = 2.1 Hz), 11.8 (brs)

5,7-Dihydroxy 6- (2,4-dichlorophenyl) imidazo [1,2-a] pyrimidine 7.0 g, DBU 3.95 g and a mixture of oxychloride phosphorus 25 ml were refluxed. Heated under the conditions for 5 hours. After the reaction mixture was concentrated, chloroform and a saturated aqueous sodium hydrogen carbonate solution were added to the residue, and the layers were separated. The organic layer was washed successively with a saturated aqueous solution of sodium hydrogen carbonate and a saturated saline solution, dried over sodium sulfate, and concentrated. The residue was washed with chloroform to give 5,17-dichloro-6_ (2,4-dichlorophenyl) imidazo [1,2-a] pyrimidine (2.17 g).

_{1 H-NMR (CDC 1 3} , TMS) δ (p pm): 7. 27 (1 H, d

, J = 8.9 Hz), 7.43 (1H, dd, J = 1.9 Hz, 8.2 Hz), 7.60 (1H, d, 1 = 2. lHz), 7.73 (1H, d , J = 1.4 Hz), 7.90 (1H, d, J1.7Hz) Next, formulation examples are shown. In addition, parts represent parts by weight.

Formulation Example 1

 50 parts of each of the compounds of the present invention (1) to (24), 3 parts of calcium ligninsulfonate, 2 parts of magnesium lauryl sulfate and 45 parts of synthetic hydrous silicon dioxide are thoroughly pulverized and mixed to obtain each wettable powder. Get.

Formulation example 2.

 20 parts of each of the compounds (1) to (24) of the present invention and 1.5 parts of sorbitan triolate are mixed with 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol, and the mixture is pulverized by wet milling. After pulverization, 40 parts of an aqueous solution containing 0.05 parts of xanthan gum and 0.1 parts of aluminum magnesium silicate are added thereto, and 10 parts of propylene glycol are further added and mixed with stirring to obtain each flowable preparation.

Formulation Example 3

 Each of the compounds of the present invention (1) to (24), 2 parts of each, 88 parts of kaolin clay and 10 parts of talc are thoroughly pulverized and mixed to obtain each powder.

Formulation Example 4

Each of the present compounds (1) to (24) is mixed well with 5 parts of each, 14 parts of polyoxyethylene styryl phenol olenoether, 6 parts of calcium dodecylbenzenesulfonate and 75 parts of xylene to obtain each emulsion.

Formulation Example 5

 After thoroughly pulverizing and mixing 2 parts of each of the compounds (1) to (24) of the present invention, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65 parts of olcin clay, water may be added. Each granule is obtained by kneading and granulating and drying.

Formulation Example 6

A mixture of 10 parts of each of the compounds (1) to (24) of the present invention, 35 parts of white carbon containing 50 parts of polyoxyethylene alkyl ether termonium salt and 55 parts of water, and finely pulverizing by wet grinding. By the above, each preparation is obtained. Next, test examples show that the compounds of the present invention are effective in controlling plant diseases. For comparison, Japanese Patent Application Laid-Open Publication No. 2001-43978, page 17, A-74, page 17 A-74, ie, 2-phenyl-2-ene 5- (4-methinolephenyl) -17-methylimidazo [1,2—a] pyrimidine (hereinafter, referred to as Comparative compound A) was also subjected to the test.

トに砂壌土を詰め、 キユウリ （相模半白） を播種し、 温室内 で 10日間生育させた。 製剤例 6に準じて得られた本発明化合物 （1) 〜 （24 ) および比較ィヒ合物 Aの製剤の各々を、 水で 500 p pmの濃度に希釈し、 散布 液を調製した。 各々の散布液を、 前記のキユウリ子葉面に十分付着するように茎 葉散布した。 葉面上の散布液を風乾させた後、 キユウリの子葉面上に灰色かび病 菌の胞子を含有する PDA培地を置いた。 そのキユウリを 12 °C多湿下に 5日間 放置した後、 植物の病斑面積を肉眼にて観察した。 無処理の植物の病斑面積と、 薬剤を処理した植物の病斑面積を比較し、 病害の防除効果を判定した。 Comparative compound A

Were filled with sandy loam, sown with cucumber (Sagami Hanjiro), and grown in a greenhouse for 10 days. Each of the preparations of the compounds of the present invention (1) to (24) and Comparative Compound A obtained according to Formulation Example 6 was diluted with water to a concentration of 500 ppm to prepare a spray liquid. Each spray solution was sprayed on the foliage so as to be sufficiently adhered to the above-mentioned cucumber cotyledon surface. After the spray solution on the foliage was air-dried, a PDA medium containing the spores of Botrytis cinerea was placed on the cotyledon of Cucumber. After leaving the cucumber in a humid environment at 12 ° C for 5 days, the lesion area of the plant was visually observed. The lesion area of untreated plants was compared with the lesion area of plants treated with the drug, and the disease control effect was determined.

 As a result, the lesion area of cucumber treated with a spray liquid containing the present compounds (1) to (24) as an active ingredient was 30% or less of the lesion area of the untreated group. The lesion area of the cucumber treated with the spray liquid containing the comparative compound was 75% or more of the lesion area of the untreated group.

Test example 2

Each of the comparative compound A and the compound 22 dissolved in dimethyl sulfoxide was mixed with a PDA medium to a predetermined concentration (2 ppm), and poured into a sterile petri dish to prepare a plate medium. A piece of mycelium of a fungus of gray mold was inoculated in the center of the prepared medium, and cultured at 18 ° C for 60 hours, and then the flora radius was measured. As a result, the radius of the flora in the PDA medium supplemented with Compound 22 was 10% or less of the radius of the flora in the PDA medium supplemented without Compound 22. Comparative compound Radish flora in PDA medium with kazuri A It was more than 80% of the radius of the flora. . Industrial Applicability

 By using the compound of the present invention, plant diseases can be controlled.

Claims

The scope of the claims  Equation (1)

Wherein R ¹ and R ² represent a halogen atom, R ⁴ represents a halogen atom, a CI—C4 alkyl group, a C 1—C4 alkoxy group or a cyano group, and R ⁵ represents a halogen atom, a nitro group, a cyano group. Group, C1-C4 alkyl group, CI-C4 alkoxy group, C1-C4 alkylthio group, C1-C4 haloalkylthio group, C1-C4 haloanolequinole group, C1-C4 haloalkoxy group, C 11 represents a C4 acyl group, a C2-C5 alkoxycarbonyl group or a phenyl group, m represents an integer of 0 to 4, and n represents an integer of 0 to 5. When m is an integer of 2 or more, R ¹ may represent the same or different atoms, and when n is an integer of 2 or more, R ⁵ may represent the same or different atoms or groups. Good. ] An imidazopyrimidine compound represented by the formula:  2. The imidazopyrimidine compound according to claim 1, wherein in the formula (1), m is an integer of 0 to 2. 3. The imidazopyrimidine compound according to claim 1, wherein in formula (1), m is 0 or m is 1, and R ¹ is a halogenogen atom substituted at the 4-position. 4. In the formula (1), m is 0 or m is 1 and R ¹ is a halogen atom substituted at the 4- or 6-position, or m is 2 and one R ¹ 2. The imidazopyrimidine compound according to claim 1, wherein is a halogen atom substituted at the 4-position, and another R ¹ is a halogen atom substituted at the 6-position. 5. The imidazopyrimidine compound according to claim 1, wherein in the formula (1), m is 1 or 2, and at least one R ¹ is a halogen atom substituted at the 4- or 6-position. 6. In Formula (1), m is 1 and R ¹ is a halogen atom substituted at the 6-position, or m is 2 and one R ¹ is a halogen atom substituted at the 4-position. 2. The imidazopyrimidine compound according to claim 1, wherein the other R ¹ is a halogen atom substituted at the 6-position. 7. In the formula (1), m is 1, and R ¹ is a fluorine atom substituted at the 6-position or a chlorine atom substituted at the 6-position, or m is 2, and one R ¹ is R ¹ is a fluorine atom substituted at the 6-position or a chlorine atom substituted at the 6-position, and R ² is a fluorine atom substituted at the 6-position; 2. The imidazopyrimidine compound according to claim 1, which is an atom or a chlorine atom. 8. The imidazopyrimidine compound according to claim 1, wherein in the formula (1), R ¹ and R ² are each independently a fluorine atom or a chlorine atom. 9. The imidazopyrimidine compound according to any one of claims 1 to 8, wherein in the formula (1), R ⁴ is a halogen atom or a C1-C4 alkyl group. 10. The imidazopyrimidine compound according to any one of claims 1 to 8, wherein in the formula (1), R ⁴ is a halogen atom.  11. A germicidal composition comprising the imidazopyrimidine compound according to claim 1 as an active ingredient.  12. Use of the imidazopyrimidine conjugate according to claim 1 as an active ingredient of a bactericidal composition. 13. A method for controlling plant diseases, wherein the imidazopyrimidine compound according to claim 1 is applied to a plant or soil where the plant is grown.