WO2010119879A1

WO2010119879A1 - Pyrimidine compound and its use for pest control

Info

Publication number: WO2010119879A1
Application number: PCT/JP2010/056629
Authority: WO
Inventors: Hiroki Tomioka; Hajime Mizuno; Daisuke Takaoka; Hiroshi Ikegami; Yoshihiko Nokura
Original assignee: Sumitomo Chemical Co Ltd
Current assignee: Sumitomo Chemical Co Ltd
Priority date: 2009-04-16
Filing date: 2010-04-07
Publication date: 2010-10-21
Anticipated expiration: 2011-10-16
Also published as: AR076296A1; JP2010265259A

Abstract

A pyrimidine compound represented by formula (1) has a control effect against pests and is useful as an active ingredient of a pest controlling agent.

Description

DESCRIPTION PYRIMIDINE COMPOUND AND ITS USE FOR PEST CONTROL

Technical Field The present invention relates to a pyrimidine compound and its use in pest control.

Background Art

Compounds having control activity against pests have been found and developed as active ingredients of a pest controlling agent. Certain pyrimidine compounds are known in, for example, US200/0005403 Al, JP-A-63-039875 and WO 99/41253.

Disclosure of Invention

An object of the present invention is to provide a novel compound having a control activity against pests.

The present inventors have studied so as to find a compound having a control activity against pests and found that a pyrimidine compound represented by formula (1) shown below has a control activity against pests, thus leading to the present invention.

That is, the present invention provides the following. [1] A pyrimidine compound represented by formula (1) :

(D wherein

Q represents oxygen or -S(O)_n-, n represents 0, 1 or 2, G¹ represents nitrogen or CR⁶ , R¹ , R² and R⁶ are the same or different and represent hydrogen, halogen, a nitro group, a cyano group, a chain Cl- C6 hydrocarbon group optionally substituted with halogen, - L¹R⁷, -C (=0) R⁸ , a phenyl group optionally substituted with one or more members selected from Group A, or a 5- or 6- membered aromatic heterocyclic group optionally substituted with one or more members selected from Group A, L¹ represents oxygen, -S(O)_n- or -NR⁹-,

R⁷ represents hydrogen or a chain C1-C6 hydrocarbon group optionally substituted with halogen, provided that R⁷ is not hydrogen when L¹ is -S(O)_n- and n is 1 or 2,

R⁸ represents hydrogen, a hydroxy group, an amino group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C1-C6 alkoxy group optionally substituted with halogen, a C1-C4 alkylamino group optionally substituted with halogen, or a C2-C8 dialkylamino group optionally substituted with halogen,

R⁹ represents hydrogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or a C1-C6 alkylsulfonyl group optionally substituted with halogen, R³ represents hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen, or - L²R¹⁰, R⁴ represents hydrogen, halogen, a nitro group, a cyano group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen, -L²R¹⁰, -C(=O)R¹¹, a phenyl group optionally substituted with one or more members selected from Group A, or a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more members selected from Group A,

L² represents oxygen, -S(O)_n- or -NR¹²-,

R¹⁰ represents hydrogen or a chain C1-C6 hydrocarbon group optionally substituted with halogen, provided that R¹⁰ is not hydrogen when L² is -S(O)_n- and n is 1 or 2,, R¹¹ represents hydrogen, a hydroxy group, an amino group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C1-C6 alkoxy group optionally substituted with halogen, a C1-C4 alkylamino group optionally substituted with halogen, or a C2-C8 dialkylamino group optionally substituted with halogen,

R¹² represents hydrogen, a chain Cl-Cβ hydrocarbon group optionally substituted with halogen, or a C1-C6 alkylsulfonyl group optionally substituted with halogen, R⁵ represents a C4-C10 alkyl group or a C3-C10 alkenyl group, and

Group A represents the group consisting of halogen, an amino group, a cyano group, a nitro group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a Cl- Cβ alkoxy group optionally substituted with halogen and S(O)_nR¹³, in which that R¹³ represents a C1-C6 alkyl group optionally substituted with halogen (hereinafter referred to as the present compound) . [2] The pyrimidine compound according to [1], wherein R¹, R² and R⁶ are the same or different and represent hydrogen, halogen, a nitro group, a cyano group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, -L¹R⁷ or -C(=O)R⁸.

[3] The pyrimidine compound according to [1] , wherein R¹ , R² and R⁶ are the same or different and represent hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, -L¹R⁷ or -C(=O)R⁸. [4] The pyrimidine compound according to any one of [1] to

[3] , wherein R¹ and R⁶ are the same or different and represent hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or -C(=O)R⁸.

[5] The pyrimidine compound according to any one of [1] to [4], wherein R² is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or -L¹R⁷.

[6] The pyrimidine compound according to any one of [1] to

[5] , wherein R⁴ is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3- C8 cycloalkyl group optionally substituted with halogen, or -L²R¹⁰.

[7] The pyrimidine compound according to any one of [1] to

[6], wherein R³ is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or a C3-C8 cycloalkyl group optionally substituted with halogen.

[8] The pyrimidine compound according to any one of [1] to

[6], wherein R³ is hydrogen. [9] The pyrimidine compound according to any one of [1] to

[8], wherein Q is oxygen.

[10] The pyrimidine compound according to any one of [1] to

[9], wherein R⁵ is a branched C4-C10 alkyl group, or a C3- ClO alkenyl group.

[11] The pyrimidine compound according to [1], wherein

Q is oxygen,

G¹ is nitrogen or CR⁶ ,

R¹ and R⁶ are the same or different and represent hydrogen, ha logen, or a chain C1-C6 hydrocarbon group optionally subst ituted with halogen,

R² is hydrogen, halogen, a chain C1-C6 hydrocarbon group opti onally substituted with halogen, or -L¹R⁷,

R³ is hydrogen or a chain C1-C6 hydrocarbon group optionally s ubstituted with halogen,

R⁴ is hydrogen, halogen, or a chain C1-C6 hydrocarbon grou p optionally substituted with halogen, and

R⁵ is a branched C4-C8 alkyl group, or a C3-C8 alkenyl grou

P- [12] A pest controlling agent comprising the pyrimidine compound according to any one of [1] to [11], and an inert carrier.

[13] Use of the pyrimidine compound according to any one of

[1] to [11] for controlling pests. [14] A method of controlling pests, which comprises a step of applying an effective amount of the pyrimidine compound according to any one of [1] to [11] to pests or habitats of the pests. Mode of Carrying Out the Invention

In the present compound, examples of the "halogen" include fluorine, chlorine, bromine and iodine.

In the present compound, the "chain C1-C6 hydrocarbon group" includes, for example, C1-C6 alkyl groups such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an isopentyl group, a 1- methylbutyl group, a tert-pentyl group, a neopentyl group, a hexyl group and an isohexyl group;

C2-C6 alkenyl groups such as a vinyl group, a 2- propenyl group, a 2-butenyl group, a 3-butenyl group, a 2- methyl-2-propenyl group, a 3-methyl-2-butenyl group, a 2- pentenyl group and a 2-hexenyl group; and C2-C6 alkynyl groups such as an ethynyl group, a 2- propynyl group, a 2-butynyl group and a 3-butynyl group.

In the present compound, the "chain C1-C6 hydrocarbon group optionally substituted with halogen" includes, for example, C1-C6 alkyl groups optionally substituted with halogen, such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an isopentyl group, a 1-methylbutyl group, a tert-pentyl group, a neopentyl group, a hexyl group, an isohexyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a 2, 2, 2-trifluoroethyl group, a 2, 2, 2-trichloroethyl group, a pentafluoroethyl group, a perfluoropropyl group, a perfluorobutyl group and a perfluorohexyl group; C2-C6 alkenyl groups optionally substituted with halogen, such as a vinyl group, a 2-propenyl group, a 3-chloro-2- propenyl group, a 2-chloro-2-propenyl group, a 3, 3-dichloro- 2-propenyl group, a 2-butenyl group, a 3-butenyl group, a 2- methyl-2-propenyl group, a 3-methyl-2-butenyl group, a 2- pentenyl group and a 2-hexenyl group; and

C2-C6 alkynyl groups optionally substituted with halogen, such as an ethynyl group, a 2-propynyl group, a 2-butynyl group, a 3-butynyl group, a 3-chloro-2-propynyl group and a 3-bromo-2-propynyl group.

In the present compound, the "phenyl group optionally substituted with one or more members selected from Group A" includes, for example, a phenyl group, a 2-chlorophenyl group, a 3-chlorophenyl group, a 4-chlorophenyl group, a 2- aminophenyl group, a 3-aminophenyl group, a 4-aminophenyl group, a 2-cyanophenyl group, a 3-cyanophenyl group, a 4- cyanophenyl group, a 2-nitrophenyl group, a 3-nitrophenyl group, a 4-nitrophenyl group, a 2-methylphenyl group, a 3- methylphenyl group, a 4-methylphenyl group, a 2- (trifluoromethyl) phenyl group, a 3- (trifluoromethyl) phenyl group, a 4- (trifluoromethyl) phenyl group, a 2-methoxyphenyl group, a 3-methoxyphenyl group, a 4-methoxyphenyl group, a 4- (trifluoromethoxy) phenyl group, a 4- (methylthio) phenyl group, a 4- (methylsulfinyl) phenyl group and a 4- (methylsulfonyl) phenyl group.

In the present compound, the "5- or 6-membered aromatic heterocyclic group" includes, for example, a 2- pyrrolyl group, a 2-furyl group, a 3-furyl group, a 2- thienyl group, a 3-thienyl group, a 5-pyrazolyl group, a 4- pyrazolyl group, a 2-pyridinyl group, a 3-pyridinyl group, a 4-pyridinyl group, a pyrazinyl group, a 1-pyrrolyl group and a 1-pyrazolyl group.

In the present compound, the "5- or 6-membered aromatic heterocyclic group optionally substituted with one or more members selected from Group A" includes, for example, a l-methyl-2-pyrrolyl group, a 2-furyl group, a 3- furyl group, a 5-bromo-2-furyl group, a 5-nitro-2-furyl group, a 2-methyl-3-furyl group, a 2, 5-dimethyl-3-furyl group, a 2, 4-dimethyl-3-furyl group, a 2-thienyl group, a 3- thienyl group, a 5-methyl-2-thienyl group, a 3-methyl-2- thienyl group, a l-methyl-3-trifluoromethyl-5-pyrazolyl group, a 5-chloro-l, 3-dimethyl-4-pyrazolyl group, a 2- pyridinyl group, a 3-pyridinyl group, a 4-pyridinyl group, a 2-methyl-3-pyridinyl group, a 6-methyl-3-pyridinyl group, a 2-chloro-3-pyridinyl group, a 6-chloro-3-pyridinyl group, a pyrazinyl group, a 1-pyrrolyl group and a 1-pyrazolyl group.

In the present compound, the "C1-C6 alkoxy group optionally substituted with halogen" includes, for example, a methoxy group, a trifluoromethoxy group, an ethoxy group, a 2, 2, 2-trifluoroethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group, an isobutyloxy group, a sec-butyloxy group, a tert-butyloxy group, a pentyloxy group and a hexyloxy group. In the present compound, the "C1-C6 alkylsulfonyl group optionally substituted with halogen" includes, for example, a methylsulfonyl group, a trifluoromethylsulfonyl group and an ethylsulfonyl group.

In the present compound, the "C1-C4 alkylamino group optionally substituted with halogen" includes, for example, a methylamino group, an ethylamino group, a 2,2,2- trifluoroethylamino group, a propylamino group, an isopropylamino group and a butylamino group. In the present compound, the "C2-C8 dialkylamino group optionally substituted with halogen" includes, for example, a dimethylamino group, a diethylamino group, a bis (2,2, 2- trifluoroethyl) amino group and a dipropylamino group.

In the present compound, the "C3-C8 cycloalkyl group optionally substituted with halogen" includes, for example, a cyclopropyl group, a 2, 2-difluorocyclopropyl group, a 2,2- dichlorocyclopropyl group, a 2, 2-dibromocyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group and a cyclooctyl group. In the present compound, the "C4-C10 alkyl group" includes, for example, linear C4-C10 alkyl groups such as a butyl group, a pentyl group, a hexyl group, a heptyl group and an octyl group; and branched C4-C10 alkyl groups such as an isobutyl group, a sec-butyl group, a tert-butyl group, an isopentyl group, a 1-methylbutyl group, a tert-pentyl group, a neopentyl group, an isohexyl group and a 3, 3-dimethylpentyl group.

In the present compound, the "C3-C10 alkenyl group" includes, for example, linear C3-C10 alkenyl groups such as a 2-propenyl group, a 2-butenyl group, a 3-butenyl group, a 2-pentenyl group, a 2-hexenyl group, a 2-heptenyl group and a 2-octenyl group; and branched C3-C10 alkenyl groups such as a l-methyl-2- propenyl group, a 2-methyl-2-propenyl group and a 1-methyl- 2-butenyl group.

In the present compound, the "C1-C6 alkyl group optionally substituted with halogen" includes, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an isopentyl group, a 1- methylbutyl group, a tert-pentyl group, a neopentyl group, a hexyl group, an isohexyl group, a 1, 1, 1-trifluoromethyl group, a 2, 2, 2-trifluoroethyl group and a 2,2,2- trichloroethyl group.

Examples of the present compound includes the following pyrimidine compounds. A pyrimidine compound represented by formula (1), wherein Q is oxygen.

A pyrimidine compound represented by formula (1), wherein Q is -S(O)_n-.

A pyrimidine compound represented by formula (1), wherein n is 0.

A pyrimidine compound represented by formula (1), wherein n is 1.

A pyrimidine compound represented by formula (1), wherein n is 2. A pyrimidine compound represented by formula (1), wherein R¹ is hydrogen, halogen, a nitro group, a cyano group, a chain

C1-C6 hydrocarbon group optionally substituted with halogen,

-L¹R⁷ or -C(=O)R⁸.

A pyrimidine compound represented by formula (1), wherein R¹ is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, -L¹R⁷ or -C(=0)R⁸.

A pyrimidine compound represented by formula (1), wherein R¹ is hydrogen, halogen, or a chain C1-C6 hydrocarbon group optionally substituted with halogen.

A pyrimidine compound represented by formula (1), wherein R¹ is hydrogen.

A pyrimidine compound represented by formula (1), wherein R² is hydrogen, halogen, a nitro group, a cyano group, a chain C1-C6 hydrocarbon group optionally substituted with halogen,

-L¹R⁷ or -C(=O)R⁸.

A pyrimidine compound represented by formula (1), wherein R² is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or -L¹R⁷. A pyrimidine compound represented by formula (1), wherein R² is hydrogen, halogen, or a chain C1-C6 hydrocarbon group optionally substituted with halogen.

A pyrimidine compound represented by formula (1), wherein R² is hydrogen. A pyrimidine compound represented by formula (1), wherein R¹ and R² are the same or different and represent hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or -L¹R⁷.

A pyrimidine compound represented by formula (1), wherein R¹ and R² are hydrogen.

A pyrimidine compound represented by formula (1), wherein G¹ is nitrogen.

A pyrimidine compound represented by formula (1), wherein G¹ is CR⁶ .

A pyrimidine compound represented by formula (1), wherein G¹ is CR⁶ and R⁶ is hydrogen.

A pyrimidine compound represented by formula (1), wherein R¹ is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, -L¹R⁷ or -C(=O)R⁸, R² is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or -L¹R⁷, G¹ is nitrogen or CR⁶, and R⁶ is hydrogen. A pyrimidine compound represented by formula (1), wherein R¹ is hydrogen, halogen, or a chain C1-C6 hydrocarbon group optionally substituted with halogen, R² is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or -L¹R⁷, G¹ is nitrogen or CR⁶, and R⁶ is hydrogen.

A pyrimidine compound represented by formula (1), wherein R¹ is hydrogen, R² is hydrogen or an amino group, G¹ is nitrogen or CR⁶, and R⁶ is hydrogen.

A pyrimidine compound represented by formula (1), wherein R³ is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or a C3-C8 cycloalkyl group optionally substituted with halogen. A pyrimidine compound represented by formula (1) , wherein R³ is hydrogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or -L²R¹⁰.

A pyrimidine compound represented by formula (1), wherein R³ is hydrogen or a chain C1-C6 hydrocarbon group optionally substituted with halogen. A pyrimidine compound represented by formula (1), wherein R³ is hydrogen.

A pyrimidine compound represented by formula (1), wherein R⁴ is hydrogen, halogen, a nitro group, a cyano group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen, -L²R¹⁰ or -C(=O)R¹¹.

A pyrimidine compound represented by formula (1), wherein R⁴ is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, -L²R¹⁰ or a phenyl group optionally substituted with one or more members selected from Group A.

A pyrimidine compound represented by formula (1), wherein R⁴ is hydrogen, halogen, a nitro group, a cyano group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen, or -CC=O)R¹¹.

A pyrimidine compound represented by formula (1), wherein R⁴ is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen, or -L²R¹⁰. A pyrimidine compound represented by formula (1), wherein R³ is hydrogen, R⁴ is hydrogen, halogen, a nitro group, a cyano group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen, -L²R¹⁰ or -C C=O)R¹¹. A pyrimidine compound represented by formula (1), wherein R³ is hydrogen, R⁴ is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or -L²R¹⁰.

A pyrimidine compound represented by formula (1), wherein R³ is hydrogen, R⁴ is hydrogen, chlorine or a methyl group.

A pyrimidine compound represented by formula (1), wherein R¹ , R² and R⁶ are the same or different and represent hydrogen, halogen, a nitro group, a cyano group, a chain Cl- C6 hydrocarbon group optionally substituted with halogen, - L¹R⁷ or -C(=O)R⁸.

A pyrimidine compound represented by formula (1), wherein R¹ , R² and R⁶ are the same or different and represent hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, -L¹R⁷ or -C(=O)R⁸. A pyrimidine compound represented by formula (1), wherein R¹ and R⁶ are the same or different and represent hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or -C(=O)R⁸. A pyrimidine compound represented by formula (1), wherein R¹ is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, -L¹R⁷ or -C(=O)R⁸, R² is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or -L¹R⁷, G¹ is nitrogen or CR⁶ , R⁶ is hydrogen, R³ is hydrogen, and R⁴ is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen, or -L²R¹⁰. A pyrimidine compound represented by formula (1), wherein R¹ is hydrogen, halogen or a chain C1-C6 hydrocarbon group optionally substituted with halogen, R² is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or -L¹R⁷, G¹ is nitrogen or CR⁶, R⁶ is hydrogen, R³ is hydrogen, and R⁴ is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or -L²R¹⁰.

A pyrimidine compound represented by formula (1), wherein R⁵ is a C4-C10 alkyl group. A pyrimidine compound represented by formula (1), wherein R⁵ is a branched C4-C10 alkyl group.

A pyrimidine compound represented by formula (1), wherein R⁵ is a tert-butyl group, a sec-butyl group, an isobutyl group, a 1, 2-dimethylpropyl group, a neopentyl group, an isopentyl group, a 1-methylbutyl group, a 2-methylbutyl group, a tert- pentyl group, an isohexyl group, a 3, 3-dimethylpentyl group, or a 4, 4-dimethylpentyl group.

A pyrimidine compound represented by formula (1), wherein R⁵ is a C3-C10 alkenyl group. A pyrimidine compound represented by formula (1), wherein R⁵ is a 2-propenyl group, a 2-butenyl group, a 3-butenyl group, a 2-pentenyl group, a 2-hexenyl group, a 2-heptenyl group, a 2-octenyl group, a l-methyl-2-propenyl group, a 2-methyl-2- propenyl group or a l-methyl-2-butenyl group. A pyrimidine compound represented by formula (1), wherein R⁵ is a branched C3-C10 alkenyl group.

A pyrimidine compound represented by formula (1), wherein R⁵ is a branched C4-C6 alkyl group or a C3-C6 alkenyl group. A pyrimidine compound represented by formula (1), wherein Q is oxygen and R⁵ is a C4-C10 alkyl group.

A pyrimidine compound represented by formula (1), wherein Q is oxygen and R⁵ is a branched C4-C10 alkyl group. A pyrimidine compound represented by formula (1), wherein Q is oxygen, R⁵ is a tert-butyl group, a sec-butyl group, an isobutyl group, a 1, 2-dimethylpropyl group, a neopentyl group, an isopentyl group, a 1-methylbutyl group, a 2- methylbutyl group, a tert-pentyl group, an isohexyl group, a 3, 3-dimethylpentyl group, or a 4, 4-dimethylpentyl group. A pyrimidine compound represented by formula (1), wherein R⁵ is a branched C4-C6 alkyl group.

A pyrimidine compound represented by formula (1), wherein Q is oxygen and R⁵ is a C3-C10 alkenyl group. A pyrimidine compound represented by formula (1), wherein Q is oxygen and R⁵ is a branched C3-C10 alkenyl group.

A pyrimidine compound represented by formula (1), wherein Q is oxygen, R⁵ is a 2-propenyl group, a 2-butenyl group, a 3- butenyl group, a 2-pentenyl group, a 2-hexenyl group, a 2- heptenyl group and a 2-octenyl group, a l-methyl-2-propenyl group, a 2-methyl-2-propenyl group, or a l-methyl-2- butenyl group.

A pyrimidine compound represented by formula (1), wherein Q is oxygen and R⁵ is a branched C4-C6 alkyl group or a C3- C6 alkenyl group.

A pyrimidine compound represented by formula (1), wherein Q is oxygen, G¹ is nitrogen or CR⁶ , R¹ and R⁶ are the same or different and represent hydrogen, halogen or a chain C1-C6 hydrocarbon group optionally substituted with halogen, R² is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or -L¹R⁷, R³ is hydrogen or a chain C1-C6 hydrocarbon group optionally substituted with halogen, R⁴ is hydrogen, halogen or a chain C1-C6 hydrocarbon group optionally substituted with halogen, and R⁵ is a branched C4-C8 alkyl group or a C3-C8 alkenyl group.

A pyrimidine compound represented by formula (1), wherein Q is oxygen, G¹ is nitrogen or CR⁶ , R¹ is hydrogen, halogen, A chain C1-C6 hydrocarbon group optionally substituted with halogen, -L¹R⁷ or -C(=O)R⁸, R² is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or -L¹R⁷, R⁶ is hydrogen, R³ is hydrogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or -L²R¹⁰, R⁴ is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3- C8 cycloalkyl group optionally substituted with halogen, or -L²R¹⁰, and R⁵ is a C4-C10 alkyl group or a C3-C10 alkenyl group.

A pyrimidine compound represented by formula (1), wherein Q is oxygen, G¹ is nitrogen or CR⁶ , R¹ is hydrogen, halogen, a methyl group or an amino group, R² is hydrogen, halogen, a methyl group or an amino group, R⁶ is hydrogen, R³ is hydrogen, a chain Cl-Cβ hydrocarbon group optionally substituted with halogen, or -L²R¹⁰, R⁴ is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen, or -L²R¹⁰, R⁵ is a C4- ClO alkyl group or a C3-C10 alkenyl group.

A pyrimidine compound represented by formula (1), wherein Q is oxygen, G¹ is nitrogen or CR⁶ , R¹ is hydrogen or halogen, R² is hydrogen, halogen, a methyl group or an amino group, R⁶ is hydrogen, R³ is hydrogen or a chain C1-C6 hydrocarbon group optionally substituted with halogen, R⁴ is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or -L²R¹⁰, and R⁵ is a branched C4-C10 alkyl group or a C3-C10 alkenyl group.

A pyrimidine compound represented by formula (1), wherein Q is oxygen, R¹ is hydrogen, R² is hydrogen or an amino group, G¹ is nitrogen or CR⁶ , R⁶ is hydrogen, R³ is hydrogen, R⁴ is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, and R⁵ is a branched C4-C6 alkyl group or a C3-C6 alkenyl group.

Processes for producing the present compound will be described below.

The present compound can be produced, for example, by the following (Production Process A) to (Production Process E) .

(Production Process A)

Among the present compound, the compound represented by formula (1-i) :

wherein R¹, R², R³, R⁴, R⁵ and G¹ are as defined above, and Q' represents oxygen or sulfur (hereinafter referred to as the present compound (1-i)) can be produced by reacting the compound represented by formula (2) :

wherein R¹ , R² , R³ , R⁴ and G¹ are as defined above (hereinafter referred to as the compound (2)) with the compound represented by formula (3) : R⁵-Q'-H wherein R⁵ and Q' are as defined above (hereinafter referred to as the compound (3)) .

The reaction is performed in the presence or absence of a solvent. The solvent used in the reaction includes, for example, water; ethers such as 1,4-dioxane, diethyl^'ether, tetrahydrofuran and tert-butyl methyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane and chlorobenzene; hydrocarbons such as toluene, benzene and xylene; nitriles such as acetonitrile; aprotic polar solvents such as N, N-dimethylformamide, N-methyl pyrrolidone (hereinafter referred to as NMP), 1, 3-dimethyl-2- imidazolidinone and dimethyl sulfoxide; and mixtures thereof.

The amount of the compound (3) used in the reaction is usually from 1 to 2 mol per 1 mol of the compound (2) . The reaction is usually performed in the presence of a base. The base used in the reaction includes, for example, nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2, 6-lutidine, 1, 8-diazabicyclo [5, 4, 0] 7-undecene (hereinafter referred to as DBU) and 1,5- diazabicyclo [4, 3, 0] 5-nonene; tertiary amines such as triethylamine and N, N-diisopropylethylamine; and inorganic bases such as potassium carbonate and sodium hydride.

The amount of the base used in the reaction is usually 1 mol or more per 1 mol of the compound (2) . The reaction temperature of the reaction is usually within a range from -20 to 100°C. The reaction time of the reaction is usually within a range from 0.1 to 24 hours.

After completion of the reaction, the present compound (1-i) can be isolated by pouring the reaction mixture into water followed by extraction with an organic solvent and subsequent concentration of the organic layer; pouring the reaction mixture into water followed by collection of the formed solid by filtration; or collecting a solid formed in the reaction mixture by filtration. The isolated present compound (1-i) can also be further purified by recrystallization, chromatography and so on.

The compound (2) includes, for example, the following pyrimidine compounds. A pyrimidine compound represented by formula (2), wherein G¹ is nitrogen.

A pyrimidine compound represented by formula (2), wherein G¹ is CR⁶ and R⁶ is hydrogen. A pyrimidine compound represented by formula (2), wherein R¹ is hydrogen.

A pyrimidine compound represented by formula (2), wherein R² is hydrogen.

A pyrimidine compound represented by formula (2), wherein R¹ and R² are hydrogen.

A pyrimidine compound represented by formula (2), wherein G¹ is nitrogen, R¹ and R² is hydrogen.

A pyrimidine compound represented by formula (2), wherein R³ is hydrogen. A pyrimidine compound represented by formula (2), wherein G¹ is nitrogen and R³ is hydrogen.

A pyrimidine compound represented by formula (2), wherein G¹ is CR⁶, R⁶ is hydrogen and R³ is hydrogen.

A pyrimidine compound represented by formula (2), wherein R⁴ is hydrogen, halogen, a nitro group, a cyano group, a chain

C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen or -CC=O)R¹¹.

A pyrimidine compound represented by formula (2), wherein R⁴ is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen or -L²R¹⁰.

A pyrimidine compound represented by formula (2), wherein R⁴ is halogen, a nitro group, a cyano group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3- C8 cycloalkyl group optionally substituted with halogen or - Cl=O)R¹¹.

A pyrimidine compound represented by formula (2), wherein R³ is hydrogen and R⁴ is hydrogen, halogen, a nitro group, A cyano group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen, -L²R¹⁰ or -C(O)R¹¹. A pyrimidine compound represented by formula (2), wherein R³ is hydrogen and R⁴ is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen or -

L²R¹⁰.

A pyrimidine compound represented by formula (2), wherein R³ is hydrogen and R⁴ is halogen, a ^"chain C1-C6 hydrocarbon group optionally substituted with halogen or -L²R¹⁰.

A pyrimidine compound represented by formula (2), wherein R³ is hydrogen and R⁴ is hydrogen, chlorine or a methyl group. A pyrimidine compound represented by formula (2), wherein G¹ is nitrogen or CR⁶, R⁶ is hydrogen, R¹ is hydrogen or halogen, R² is hydrogen, halogen or an amino group, R³ is hydrogen and R⁴ is halogen, a nitro group, a cyano group or a chain C1-C6 hydrocarbon group optionally substituted with halogen.

A pyrimidine compound represented by formula (2), wherein G¹ is nitrogen, R¹ is hydrogen or halogen, R² is hydrogen, halogen or an amino group, R³ is hydrogen and R⁴ is hydrogen, halogen or a chain C1-C6 hydrocarbon group optionally substituted with halogen. A pyrimidine compound represented by formula (2), wherein G¹ is nitrogen, R¹ and R² is hydrogen, R³ is hydrogen and R⁴ is hydrogen, chlorine or a methyl group.

(Production Process B) The present compound (1-i) can be produced by reacting the compound represented by formula (4):

wherein R³ , R⁴ , R⁵ and Q' are as defined above (hereinafter referred to as the compound (4)) with the compound represented by formula (5) :

wherein R¹ , R² and G¹ are as defined above (hereinafter referred to as the compound (5)) .

The reaction is performed in the presence or absence of a solvent. The solvent used in the reaction includes, for example, water; ethers such as 1,4-dioxane, diethylether, tetrahydrofuran and tert-butyl methyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane and chlorobenzene; hydrocarbons such as toluene, benzene and xylene; nitriles such as acetonitrile; aprotic polar solvents such as N, N-dimethylformamide, NMP, 1, 3-dimethyl-2- imidazolidinone and dimethyl sulfoxide; and mixtures thereof .

The amount of the compound (5) used in the reaction is usually from 1 to 2 mol per 1 mol of the compound (4) .

The reaction is usually performed in the presence of a base.

The base used in the reaction includes, for example, nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2, 6-lutidine, DBU and 1, 5-diazabicyclo [4, 3, 0] 5- nonene; tertiary amines such as triethylamine and N, N- diisopropylethylamine; and inorganic bases such as potassium carbonate and sodium hydride.

The amount of the base used in the reaction is usually 1 mol or more per 1 mol of the compound (4) .

The reaction temperature of the reaction is usually within a range from -20 to 100°C. The reaction time of the reaction is usually within a range from 0.1 to 24 hours.

The compound (4) include, for example, the following pyrimidine compounds. A pyrimidine compound represented by formula (4), wherein R³ is hydrogen.

A pyrimidine compound represented by formula (4), wherein R⁴ is hydrogen, halogen, a nitro group, a cyano group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen, or -C(O)R¹¹.

A pyrimidine compound represented by formula (4), wherein R⁴ is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen, or -L²R¹⁰.

A pyrimidine compound represented by formula (4), wherein R⁴ is hydrogen, halogen or a chain C1-C6 hydrocarbon group optionally substituted with halogen. A pyrimidine compound represented by formula (4), wherein R³ is hydrogen, R⁴ is hydrogen, halogen, a nitro group, a cyano group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen, -L²R¹⁰, or -C C=O)R¹¹; A pyrimidine compound represented by formula (4), wherein R³ is hydrogen, R⁴ is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or -

L²R¹⁰.

A pyrimidine compound represented by formula (4), wherein R³ is hydrogen, R⁴ is hydrogen, chlorine, or a methyl group. A pyrimidine compound represented by formula (4), wherein R⁵ is a C4-C10 alkyl group.

A pyrimidine compound represented by formula (4), wherein R⁵ is a branched C4-C10 alkyl group. A pyrimidine compound represented by formula (4), wherein R⁵ is a tert-butyl group, a sec-butyl group, an isobutyl group, a 1, 2-dimethylpropyl group, a neopentyl group, an isopentyl group, a 1-methylbutyl group, a 2-methylbutyl group, a tert- pentyl group, an isohexyl group, a 3, 3-dimethylpentyl group or a 4 , 4-dimethylpentyl group.

A pyrimidine compound represented by formula (4), wherein R⁵ is a C3-C10 alkenyl group.

A pyrimidine compound represented by formula (4), wherein R⁵ is a 2-propenyl group, a 2-butenyl group, a 3-butenyl group, a 2-pentenyl group, a 2-hexenyl group, a 2-heptenyl group and a 2-octenyl group, a l-methyl-2-propenyl group, a 2- methyl-2-propenyl group or a l-methyl-2-butenyl group. A pyrimidine compound represented by formula (4), wherein R⁵ is a branched C3-C10 alkenyl group. A pyrimidine compound represented by formula (4), wherein R⁵ is a branched C4-C6 alkyl group or a C3-C6 alkenyl group.

(Production Process C)

The present compound (1-i) can be produced by reacting the compound represented by formula (6) :

wherein R¹ , R² , R³ , R⁴ and G¹ are as defined above] (hereinafter referred to as the compound (6)) with the compound ( 3 ) .

The reaction is performed in the presence or absence of a solvent. The solvent used in the reaction includes, for example, water; ethers such as 1,4-dioxane, diethylether, tetrahydrofuran and tert-butyl methyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane and chlorobenzene; hydrocarbons such as toluene, benzene and xylene; nitriles such as acetonitrile; aprotic polar solvents such as N, N-dimethylformamide, NMP, 1, 3-dimethyl-2- imidazolidinone and dimethyl sulfoxide; and mixtures thereof.

The amount of the compound (3) used in the reaction is usually from 1 to 2 mol per 1 mol of the compound (6) .

The reaction is usually performed in the presence of a base. The base used in the reaction includes, for example, nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2, 6-lutidine, DBU and 1, 5-diazabicyclo [4, 3, 0] 5- nonene; tertiary amines such as triethylamine and N, N- diisopropylethylamine; and inorganic bases such as potassium carbonate and sodium hydride. The amount of the base used in the reaction is usually 1 mol or more per 1 mol of the compound ( 6) .

The reaction temperature of the reaction is usually within a range from -20 to 100°C. The reaction time of the reaction is usually within a range from 0.1 to 24 hours. After completion of the reaction, the present compound (1-i) can be isolated by pouring the reaction mixture into water followed by extraction with an organic solvent and subsequent concentration of the organic layer; pouring the reaction mixture into water followed by collection of the formed solid by filtration; or collecting a solid formed in the reaction mixture by filtration. The isolated present compound (1-i) can also be further purified by recrystallization, chromatography and so on.

The compound (6) includes, for example, the following pyrimidine compounds .

A pyrimidine compound represented by formula (6), wherein G¹ is nitrogen.

A pyrimidine compound represented by formula (6), wherein G¹ is CR⁶ and R¹ is hydrogen.

A pyrimidine compound represented by formula (6), wherein R¹ is hydrogen.

A pyrimidine compound represented by formula (6), wherein R² is hydrogen.

A pyrimidine compound represented by formula (6), wherein R¹ and R² are hydrogen.

A pyrimidine compound represented by formula (6), wherein G¹ is nitrogen, and R¹ and R² are hydrogen.

A pyrimidine compound represented by formula (6), wherein R³ is hydrogen.

A pyrimidine compound represented by formula (6), wherein G¹ is nitrogen and R³ is hydrogen.

A pyrimidine compound represented by formula (6), wherein G¹ is CR⁶, R⁶ is hydrogen and R³ is hydrogen.

A pyrimidine compound represented by formula (6), wherein R⁴ is hydrogen, halogen, a nitro group, a cyano group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen, or -C C=O) R^{1 1} .

A pyrimidine compound represented by formula (6), wherein R⁴ is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen, or -L²R¹⁰.

A pyrimidine compound represented by formula (6), wherein R⁴ is halogen, a nitro group, a cyano group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3- C8 cycloalkyl group optionally substituted with halogen, or -CC=O)R¹¹.

A pyrimidine compound represented by formula (6), wherein R³ is hydrogen and R⁴ is hydrogen, halogen, a nitro group, a cyano group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen, -L²R¹⁰ or -CC=O)R¹¹;

A pyrimidine compound represented by formula (6), wherein R³ is hydrogen and R⁴ is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or - L²R¹⁰. A pyrimidine compound represented by formula (6), wherein R³ is hydrogen and R⁴ is halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or -L²R¹⁰. A pyrimidine compound represented by formula (6), wherein R³ is hydrogen and R⁴ is hydrogen, chlorine or a methyl group. A pyrimidine compound represented by formula (6), wherein G¹ is nitrogen or CR⁶, R⁶ is hydrogen, R¹ is hydrogen or halogen, R² is hydrogen, halogen or an amino group, R³ is hydrogen and R⁴ is halogen, a nitro group, a cyano group or a chain C1-C6 hydrocarbon group optionally substituted with halogen .

A pyrimidine compound represented by formula (6), wherein G¹ is nitrogen, R¹ is hydrogen or halogen, R² is hydrogen, halogen or an amino group, R³ is hydrogen and R⁴ is hydrogen, halogen or a chain C1-C6 hydrocarbon group optionally substituted with halogen.

A pyrimidine compound represented by formula (6), wherein G¹ is nitrogen, R¹ and R² is hydrogen, R³ is hydrogen and R⁴ is hydrogen, chlorine or a methyl group.

(Production Process D)

The present compound (1-i) can be produced by reacting the compound represented by formula (7) : R³

^Hv^yy R²v*^{1 (7)} wherein R¹ , R² , R³ , R⁴ , G¹ and Q' are as defined above

(hereinafter referred to as the compound (7)) with the compound represented by formula (8) :

R⁵-L wherein R⁵ is as defined above, L represents a leaving group (chlorine, bromine, iodine, a paratoluenesulfonyloxy group, a methanesulfonyloxy group and so on) (hereinafter referred to as the compound (8)) .

The reaction is performed in the presence or absence of a solvent. The solvent used in the reaction includes, for example, water; ethers such as 1,4-dioxane, diethylether, tetrahydrofuran and tert-butyl methyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane and chlorobenzene; hydrocarbons such as toluene, benzene and xylene; nitriles such as acetonitrile; aprotic polar solvents such as N,N-dimethylformamide, NMP, 1, 3-dimethyl-2- imidazolidinone and dimethyl sulfoxide; and mixtures thereof.

The amount of the compound (8) used in the reaction is usually from 1 to 2 mol per 1 mol of the compound (7) .

The reaction is usually performed in the presence of a base. The base used in the reaction includes, for example, nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2, 6-lutidine, DBU and 1, 5-diazabicyclo [4 , 3, 0] 5- nonene; tertiary amines such as triethylamine and N, N- diisopropylethylamine; and inorganic bases such as potassium carbonate and sodium hydride. The amount of the base used in the reaction is usually 1 mol or more per 1 mol of the compound ( 7 ) . The reaction temperature of the reaction is usually within a range from -20 to 100⁰C. The reaction time of the reaction is usually within a range from 0.1 to 24 hours.

After completion of the reaction, the present compound (1-i) can be isolated by pouring the reaction mixture into water followed by extraction with an organic solvent and subsequent concentration of the organic layer; ; pouring the reaction mixture into water followed by collection of the formed solid by filtration; or collecting a solid formed in the reaction mixture by filtration. The isolated present compound (1-i) can also be further purified by recrystallization, chromatography and so on.

The compound (7) includes, for example, the following pyrimidine compounds.

A pyrimidine compound represented by formula (7), wherein G¹ is nitrogen.

A pyrimidine compound represented by formula (I] wherein G¹ is CR⁶ and R⁶ is hydrogen. A pyrimidine compound represented by formula (I] _ wherein R¹ is hydrogen.

A pyrimidine compound represented by formula (7), wherein R² is hydrogen.

A pyrimidine compound represented by formula (7), wherein R¹ and R² are hydrogen.

A pyrimidine compound represented by formula (7), wherein G¹ is nitrogen, and R¹ and R² are hydrogen.

A pyrimidine compound represented by formula (7), wherein R³ is hydrogen. A pyrimidine compound represented by formula (7), wherein G¹ is nitrogen and R³ is hydrogen.

A pyrimidine compound represented by formula (7), wherein G¹ is CR⁶, R⁶ is hydrogen and R³ is hydrogen.

A pyrimidine compound represented by formula (7), wherein R⁴ is hydrogen, halogen, a nitro group, a cyano group, a chain

C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen, or -CC=O)R¹¹.

A pyrimidine compound represented by formula (7), wherein R⁴ is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen, or -L²R¹⁰. A pyrimidine compound represented by formula (7), wherein R⁴ is halogen, a nitro group, a cyano group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3- C8 cycloalkyl group optionally substituted with halogen, or -C(O)R¹¹. A pyrimidine compound represented by formula (7), wherein R³ is hydrogen and R⁴ is hydrogen, halogen, a nitro group, a cyano group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen, -L²R¹⁰ or -C(=O)R^1:L. A pyrimidine compound represented by formula (7), wherein R³ is hydrogen and R⁴ is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or -

L²R¹⁰.

A pyrimidine compound represented by formula (7), wherein R³ is hydrogen and R⁴ is halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or -L²R¹⁰.

A pyrimidine compound represented by formula (7), wherein R³ is hydrogen and R⁴ is hydrogen, chlorine or a methyl group. A pyrimidine compound represented by formula (7), wherein Q' is oxygen, R³ is hydrogen and R⁴ is hydrogen, chlorine or a methyl group.

A pyrimidine compound represented by formula (7), wherein G¹ is nitrogen, R¹ and R² are hydrogen, Q' is oxygen, R³ is hydrogen and R⁴ is hydrogen, chlorine or a methyl group. (Production Process E)

Among the present compound, the compound represented by formula (1-ii) : R³

^RVVS R²' ^<1"π) wherein R¹, R², R³, R⁴, R⁵ and G¹ are as defined above, and Q" represents -S(O)- or -S(O)₂- (hereinafter referred to as the present compound (1-ii)), the compound represented by formula (1-iii) :

wherein R¹ , R² , R³ , R⁴ , R⁵ and G¹ are as defined above

(hereinafter referred to as the compound (1-iii)), and an oxidizing agent.

Processes for producing intermediates in the production of the present compound will be described below.

(Reference Production Process 1)

The compound (2) can be produced by reacting the compound represented by formula (9) :

wherein R³ and R⁴ are as defined above (hereinafter referred to as the compound (9)) with the compound represented by the compound (5) .

The amount of the compound (5) used in the reaction is usually from 1 to 2 mol per 1 mol of the compound (9) .

The reaction is usually performed in the presence of a base. The base used in the reaction includes, for example, nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2, 6-lutidine, DBU and 1, 5-diazabicyclo [4, 3, 0] 5- nonene; tertiary amines such as triethylamine and N, N- diisopropylethylamine; and inorganic bases such as potassium carbonate and sodium hydride. The amount of the base used in the reaction is usually 1 mol or more per 1 mol of the compound (9) .

The reaction temperature of the reaction is usually within a range from -20 to 100°C. The reaction time of the reaction is usually within a range from 0.1 to 24 hours. After completion of the reaction, the present compound (2) can be isolated by pouring the reaction mixture into water followed by extraction with an organic solvent and subsequent concentration of the organic layer; pouring the reaction mixture into water followed by collection of the formed solid by filtration; or collecting a solid formed in the reaction mixture by filtration. The isolated present compound (2) can also be further purified by recrystallization, chromatography and so on.

(Reference Production Process 2)

The compound (4) can be produced by reacting the compound (9) with the compound (3) .

The amount of the compound (3) used in the reaction is usually from 1 to 2 mol per 1 mol of the compound (9) .

The reaction is usually performed in the presence of a base. The base used in the reaction includes, for example, nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2, 6-lutidine, DBU and 1, 5-diazabicyclo [4, 3, 0] 5- nonene; tertiary amines such as triethylamine and N, N- diisopropylethylamine; and inorganic bases such as potassium carbonate and sodium hydride. The amount of the base used in the reaction is usually 1 mol or more per 1 mol of the compound ( 9) .

The reaction temperature of the reaction is usually within a range from 0 to 100°C. The reaction time of the reaction is usually within a range from 0.1 to 24 hours.

After completion of the reaction, the present compound (4) can be isolated by pouring the reaction mixture into water followed by extraction with an organic solvent and subsequent concentration of the organic layer; pouring the reaction mixture into water followed by collection of the formed solid by filtration; or collecting a solid formed in the reaction mixture by filtration. The isolated present compound (4) can also be further purified by recrystallization, chromatography and so on.

(Reference Production Process 3)

The compound (6) can be produced by reacting the compound (9) with the compound (5).

The amount of the compound (5) used in the reaction is usually from 2 to 3 mol per 1 mol of the compound (9) .

The reaction is usually performed in the presence of a base. The base used in the reaction includes, for example, nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2, 6-lutidine, DBU and 1, 5-diazabicyclo [4, 3, 0] 5- nonene; tertiary amines such as triethylamine and N, N- diisopropylethylamine; and inorganic bases such as potassium carbonate and sodium hydride. The amount of the base used in the reaction is usually 2 mol or more per 1 mol of the compound ( 9) .

The reaction temperature of the reaction is usually within a range from 0 to 100⁰C. The reaction time of the reaction is usually within a range from 0.1 to 24 hours.

After completion of the reaction, the present compound (6) can be isolated by pouring the reaction mixture into water followed by extraction with an organic solvent and subsequent concentration of the organic layer; pouring the reaction mixture into water followed by collection of the formed solid by filtration; or collecting a solid formed in the reaction mixture by filtration. The isolated present compound (6) can also be further purified by recrystallization, chromatography and so on. (Reference Production Process 4)

Among the compound (7), the compound represented by formula (7-i) :

wherein R¹ , R² , R³ , R⁴ and G¹ are as defined above (hereinafter referred to as the compound (7-i) ) can be produced, for example, by subjecting the compound represented by formula (Y) :

wherein R¹ , R² , R³ , R⁴ and G¹ are as defined above, to a hydrolysis reaction.

The reaction is usually performed in the presence of a base or an acid in water. An organic solvent may be added to the reaction. The organic solvent includes, for example, ethers such as 1,4-dioxane, diethylether, tetrahydrofuran, tert-butyl methyl ether and diglyme; hydrocarbons such as toluene, benzene and xylene; and nitriles such as acetonitrile .

The base used in the reaction includes, for example, inorganic bases such as potassium carbonate, sodium hydroxide, potassium hydroxide and sodium hydride; nitrogen- containing heterocyclic compounds such as pyridine, picoline, 2, 6-lutidine, DBU and 1, 5-diazabicyclo [4, 3, 0] 5- nonene; and tertiary amines such as triethylamine and N, N- diisopropylethylamine . When the reaction is performed in the presence of the base, the amount of the based used in the reaction is usually from 0.1 to 4 mol per 1 mol of the compound ( 6) .

The acid used in the reaction includes, for example, inorganic acids such as hydrochloric acid, bromic acid and sulfuric acid; and organic acids such as acetic acid and paratoluenesulfonic acid. When the reaction is performed in the presence of the acid, the amount of the acid used in the reaction is usually 0.1 mol or more per 1 mol of the compound (6) . The reaction temperature of the reaction is usually within a range from 20 to 120°C. The reaction time of the reaction is usually within a range from 0.1 to 24 hours.

After the completion of the reaction, the compound (7) can be isolated by pouring the reaction mixture into water, extracting with an organic solvent and concentrating the organic layer; collecting a solid produced by pouring the reaction mixture into water by filtration; or collecting a solid produced in the reaction mixture by filtration. The isolated compound (7) can further purified by chromatography, distillation and so on.

(Reference Production Process 5)

Among the compound (7), the compound represented by formula (7-ii) :

wherein R¹ , R² , R³ , R⁴ and G¹ are as defined above (hereinafter referred to as the compound (7-ii) ) can be produced by reacting the compound (7-i) with a sulfuration agent .

The reaction is performed in the presence or absence of a solvent. The solvent used in the reaction includes, for example, ethers such as 1,4-dioxane, diethylether, tetrahydrofuran, tert-butyl methyl ether and diglyme; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane and chlorobenzene; hydrocarbons such as toluene, benzene and xylene; nitriles such as acetonitrile; pyridines such as pyridine, picoline and lutidine; and mixtures thereof.

The sulfuration agent used in the reaction includes, for example, diphosphorus pentasulfide and Lawesson' s reagent (2, 4-bis (4-methoxyphenyl) -1, 3-dithia-2, 4- diphosphetane 2, 4-disulfide) . The amount of the sulfuration agent used in the reaction is usually 1 mol or more per 1 mol of the compound (7-i) .

The reaction temperature of the reaction is usually within a range from 0⁰C to 200°C. The reaction time of the reaction is usually within a range from 1 to 24 hours.

After completion of the reaction, the present compound (7-ii) can be isolated by pouring the reaction mixture into water followed by extraction with an organic solvent and subsequent concentration of the organic layer; pouring the reaction mixture into water followed by collection of the formed solid by filtration; or collecting a solid formed in the reaction mixture by filtration. The isolated present compound (7-ii) can also be further purified by recrystallization, chromatography and so on.

Specific examples of the present compound include the following. A compound represented by formula (A) :

wherein R¹ and R³ represent hydrogen, Q represents oxygen, and R² , R⁵ , G¹ and R⁶ represent any one of the combinations shown in Table 1 to Table 3.

A compound represented by formula (B)

wherein R¹ and R³ represent hydrogen, Q represents oxygen, and R² , R⁵ , G¹ and R⁶ represent any one of the combinations described in Table 1 to Table 3.

A compound represented by formula (C) :

A compound represented by formula (D) :

A compound represented by formula (E) :

wherein R¹ and R³ represent hydrogen, Q represents oxygen, and R² , R⁵ , G¹ and R⁶ represent any one of the combinations described in Table 1 to Table 3. A compound represented by formula (F) :

A compound represented by formula (G) : .

A compound represented by formula (H) :

wherein R¹ and R³ represent hydrogen, Q represents sulfur, and R² , R⁵ , G¹ and R⁶ represent any one of the combinations described in Table 1 to Table 3.

A compound represented by formula (I) :

a compound represented by formula (J) :

wherein R¹ and R³ represent hydrogen, Q represents sulfur, and R² , R⁵ , G¹ and R⁶ represents any one of the combinations described in Table 1 to Table 3.

Pests against which the present compound has an activity include, for example, noxious arthropods such as noxious insects and noxious acarines, and nematodes. Specific examples of these pests include the following.

Hemiptera:

Planthoppers (Delphacidae) such as small brown planthopper (Laodelphax striatellus) , brown rice planthopper (Nilaparvata lugens) , and white-backed rice planthopper

(Sogatella furcifera) ; leafhoppers (Deltocephalidae) such as green rice leafhopper (Nephotettix cincticeps), green rice leafhopper (Nephotettix virescens) , and tea green leafhopper (Empoasca onukii) ; aphids (Aphididae) such as cotton aphid

(Aphis gossypii), green peach aphid (Myzus persicae) , cabbage aphid (Brevicoryne brassicae) , piraea aphid (Aphis spiraecola) , potato aphid (Macrosiphum euphorbiae) , foxglove aphid (Aulacorthum solani) , oat bird-cherry aphid

(Rhopalosiphum padi) , tropical citrus aphid (Toxoptera citricidus) , and mealy plum aphid (Hyalopterus pruni) ; stink bugs (Pentatomidae) such as green stink bug (Nezara antennata) , bean bug (Riptortus clavetus) , rice bug (Leptocorisa chinensis) , white spotted spined bug

(Eysarcoris parvus) , and stink bug (Halyomorpha mista) ; whiteflies (Aleyrodidae) such as greenhouse whitefly

(Trialeurodes vaporariorum) , sweetpotato whitefly (Bemisia tabaci) , citrus whitefly (Dialeurodes citri) , and citrus spiny white fly (Aleurocanthus spiniferus) ; scales

(Coccidae) such as Calfornia red scale (Aonidiella aurantii) , San Jose scale (Comstockaspis perniciosa) , citrus north scale (Unaspis citri) , red wax scale (Ceroplastes rubens) , cottonycushion scale (Icerya purchasi) , Japanese mealybug (Planococcus kraunhiae) , Cosmstock mealybug

(Pseudococcus longispinis) , and white peach scale

(Pseudaulacaspis pentagona) ; lace bugs (Tingidae) ; cimices such as Cimex lectularius; psyllids (Psyllidae) .

Lepidoptera:

Pyralid moths (Pyralidae) such as rice stem borer (Chilo suppressalis) , yellow rice borer (Tryporyza incertulas) , rice leafroller (Cnaphalocrocis medinalis), cotton leafroller (Notarcha derogata) , Indian meal moth (Plodia interpunctella) , oriental corn borer (Ostrinia furnacalis), cabbage webworm (Hellula undalis) , and bluegrass webworm (Pediasia teterrellus) ; owlet moths (Noctuidae) such as common cutworm (Spodoptera litura) , beet armyworm (Spodoptera exigua) , armyworm (Pseudaletia separata) , cabbage armyworm (Mamestra brassicae) , black cutworm (Agrotis ipsilon) , beet semi-looper (Plusia nigrisigna) , Thoricoplusia spp., Heliothis spp., and Helicoverpa spp.; white butterflies (Pieridae) such as common white (Pieris rapae) ; tortricid moths (Tortricidae) such as Adoxophyes spp., oriental fruit moth (Grapholita molesta) , soybean pod borer (Leguminivora glycinivorella) , azuki bean podworm (Matsumuraeses azukivora) , summer fruit tortrix (Adoxophyes orana fasciata) , smaller tea tortrix (Adoxophyes honmai . ) , oriental tea tortrix (Homona magnanima) , apple tortrix (Archips fuscocupreanus) , and codling moth (Cydia pomonella) ; leafblotch miners (Gracillariidae) such as tea leafroller (Caloptilia theivora) , and apple leafminer (Phyllonorycter ringoneella) ; Carposinidae such as peach fruit moth (Carposina niponensis) ; lyonetiid moths (Lyonetiidae) such as Lyonetia spp.; tussock moths (Lymantriidae) such as Lymantria spp., and Euproctis spp.; yponomeutid moths (Yponomeutidae) such as diamondback (Plutella xylostella) ; gelechiid moths (Gelechiidae) such as pink bollworm (Pectinophora gossypiella) , and potato tubeworm (Phthorimaea operculella) ; tiger moths and allies (Arctiidae) such as fall webworm (Hyphantria cunea) ; tineid moths (Tineidae) such as casemaking clothes moth (Tinea translucens) , and webbing clothes moth (Tineola bisselliella) .

Thysanoptera :

Thrips (Thripidae) such as yellow citrus thrips (Frankliniella occidentalis) , melon thrips (Thrips palmi) , yellow tea thrips (Scirtothrips dorsalis), onion thrips (Thrips tabaci) , flower thrips (Frankliniella intonsa) .

Diptera: Culices such as common mosquito (Culex pipiens pallens) , Cluex tritaeniorhynchus, and Cluex quinquefasciatus; Aedes spp. such as yellow fever mosquito (Aedes aegypti) , and Asian tiger mosquito (Aedes albopictus) ; Anopheles spp. such as Anopheles sinensis; chironomids (Chironomidae) ; house flies (Muscidae) such as Musca domestica, and Muscina stabulans; blow flies (Calliphoridae) ; flesh flies (Sarcophagidae) ; little house flies (Fanniidae) ; anthomyiid flies (Anthomyiidae) such as seedcorn fly (Delia platura) , and onion fly (Delia antiqua) ; leafminer flies (Agromyzidae) such as rice leafminer (Agromyza oryzae) , little rice leafminer (Hydrellia griseola) , tomato leafminer (Liriomyza sativae) , legume leafminer (Liriomyza trifolii) , and garden pea leafminer (Chromatomyia horticola) ; gout flies (Chloropidae) ^"such as rice stem maggot (Chlorops oryzae) ; fruit flies

(Tephritidae) such as melon fly (Dacus cucurbitae) , and Meditteranean fruit fly (Ceratitis capitata) ; Drosophilidae; humpbacked flies (Phoridae) such as Megaselia spiracularis; moth flies (Psychodidae) such as Clogmia albipunctata; Simuliidae; Tabanidae such as horsefly (Tabanus trigonus) ; stable flies.

Coleoptera : Corn root worms (Diabrotica spp.) such as Western corn root worm (Diabrotica virgifera virgifera) , and Sourthern corn root worm (Diabrotica undecimpunctata howardi) ; scarabs (Scarabaeidae) such as cupreous chafer (Anomala cuprea) , soybean beetle (Anomala rufocuprea) , and Japanese beetle (Popillia japonica) ; weevils such as maize weevil

(Sitophilus zeamais) , rice water weevil (Lissorhoptrus oryzophilus) , azuki bean weevil (Callosobruchus chinensis) , rice curculio (Echinocnemus squameus) , boll weevil (Anthonomus grandis) , and hunting billbug (Sphenophorus venatus) ; darkling beetles (Tenebrionidae) such as yellow mealworm (Tenebrio molitor) , and red flour beetle (Tribolium castaneum) ; leaf beetles (Chrysomelidae) such as rice leaf beetle (Oulema oryzae) , cucurbit leaf beetle (Aulacophora femoralis) , striped flea beetle (Phyllotreta striolata) , and Colorado potato beetle (Leptinotarsa decemlineata) ; dermestid beetles (Dermestidae) such as varied carper beetle (Anthrenus verbasci), and hide beetle (Dermestes maculates); deathwatch beetles (Anobiidae) such as cigarette beetle (Lasioderma serricorne) ; Epilachna such as Twenty-eight- spotted ladybird (Epilachna vigintioctopunctata) ; bark beetles (Scolytidae) such as powder-post beetle (Lyctus brunneus) , and pine shoot beetle (Tomicus piniperda) ; false powder-post beetles (Bostrychidae) ; spider beetles (Ptinidae); longhorn beetles (Cerambycidae) such as white- spotted longicorn beetle (Anoplophora malasiaca) ; click beetles (Agriotes spp.); Paederus fuscipens.

Orthoptera: Asiatic locust (Locusta migratoria) , African mole cricket (Gryllotalpa africana) , rice grasshopper (Oxya yezoensis) , rice grasshopper (Oxya japonica), Gryllidae.

Hymenoptera: Ants (Formicidae) such as pharaoh ant (Monomorium pharaosis) , negro ant (Formica fusca japonica) , black house ant (Ochetellus glaber) , Pristomyrmex pungens, Pheidole noda, leaf-cutting ant (Acromyrmex spp.) , and fire ant (Solenopsis spp. ) ; hornets (Vespidae) ; bethylid wasps (Betylidae) ; sawflies (Tenthredinidae) such as cabbage sawfly (Athalia rosae) , and Athalia japonica.

Nematoda :

Aphelenchoides besseyi, Nothotylenchus acris, Meloidogyne incognita, Meloidogyne hapla, Meloidogyne javanica, Heterodera glycines, Globodera rostochiensis, Pratylenchus coffeae, Pratylenchus neglectus.

Blattodea: German cockroach (Blattella germanica) , smokybrown cockroach (Periplaneta fuliginosa) , American cockroach (Periplaneta americana) , Periplaneta brunnea, oriental cockroach (Blatta orientalis) ; Acarina :

Spider mites (Tetranychidae) such as two-spotted spider mite (Tetranychus urticae) , Kanzawa spider mite (Tetranychus kanzawai) , citrus red mite (Panonychus citri) , European red mite (Panonychus ulmi) , and Oligonychus spp.; eriophyid mites (Eriophyidae) such as pink citrus rust mite (Aculops pelekassi) , Phyllocoptruta citri, tomato rust mite (Aculops lycopersici) , purple tea mite (Calacarus carinatus), pink tea rust mite (Acaphylla theavagran) , Eriophyes chibaensis, and apple rust mite (Aculus schlechtendali) ; tarosonemid mites (Tarsonemidae) such as broad mite (Polyphagotarsonemus latus) ; false spider mites (Tenuipalpidae) such as Brevipalpus phoenicis; Tuckerellidae; ticks (Ixodidae) such as Haemaphysalis longicornis, Haemaphysalis flava, Dermacentor taiwanicus,

Ixodes ovatus, Ixodes persulcatus, black legged tick (Ixodes scapularis) , Boophilus microplus, and Rhipicephalus sanguineus; acarid mites (Acaridae) such as mold mite (Tyrophagus putrescentiae) , and Tyrophagus similis; house dust mites (Pyroglyphidae) such as Dermatophagoides farinae, and Dermatophagoides ptrenyssnus; cheyletide mites (Cheyletidae) such as Cheyletus eruditus, Cheyletus malaccensis, and Cheyletus moorei; parasitoid mites (Dermanyssidae) such as tropical rat mite (Ornithonyssus bacoti) , northern fowl mite (Ornithonyssus sylviarum) , and poultry red mite (Dermanyssus gallinae) ; chiggers (Trombiculidae) such as Leptotrombidium akamushi; spiders (Araneae) such as Japanese foliage spider (Chiracanthium japonicum) , redback spider (Latrodectus hasseltii) . The pest controlling agent of the present invention contains the present compound and an inert carrier. Generally, the pest controlling agent of the present invention is a formulation obtained by mixing the present compound and an inert carrier such as a solid carrier, a liguid carrier and a gaseous carrier, and further adding a surfactant and other adjuvant for formulation, if necessary.

The formulation includes, for example, an emulsion, an oil solution, a powder, a granule, a wettable powder, a flowable formulation, a microcapsule, an aerosol, a smoking agent, a poison bait, and a resin formulation. In the pest controlling agent of the present invention, the present compound is usually contained in an amount of 0.01% to 95% by weight.

The solid carrier used for formulation includes, for example, a fine power and a granule of clays (e.g., kaolin clay, diatomite, bentonite, Fubasami clay, and acid clay) , synthetic hydrated silicon oxide, talc, ceramic, other inorganic minerals (e.g., sericite, quartz, sulfur, activated carbon, calcium carbonate, hydrated silica) or chemical fertilizers (e.g., ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, and ammonium chloride) .

The liquid carrier includes, for example, water, alcohols (e.g., methanol, ethanol, isopropyl alcohol, butanol, hexanol, benzyl alcohol, ethylene glycol, propylene glycol, phenoxyethanol) , ketones (e.g., acetone, methyl ethyl ketone, cyclohexanone) , aromatic hydrocarbons (e.g., toluene, xylene, ethylbenzene, dodecylbenzene, phenylxylylethane, methylnaphthalene) , aliphatic hydrocarbons (e.g., hexane, cyclohexane, kerosine, light oil), esters (e.g., ethyl acetate, butyl acetate, isopropyl mylistate, ethyl oleate, diisopropyl adipate, diisobutyl adipate, propyleneglycol monomethyl ether acetate) , nitriles (e.g., acetonitrile, isobutyronitrile) , ethers (e.g., diisopropyl ether, 1,4-dioxane, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether, 3-methoxy-3-methyl-l- butanol) , acid amides (e.g., N, N-dimethylformamide, N, N- dimethylacetamide) , halogenated hydrocarbons (e.g., dichloromethane, trichloroethane, tetrachlorocarbon) , sulfoxides (e.g., dimethylsulfoxide) , propylene carbonate, and vegetable oils (e.g., soy bean oil, cotton seed oil) .

The gaseous carrier includes, for example, fluorocarbo ns, butane gas, liquefied petroleum gas (LPG) , dimethyl ether , and carbon dioxide.

The surfactant includes, for example, nonionic surfactant, such as polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, polyethyleneglycol fatty acid ester; and anionic surfactant, such as alkylsulfonic acid salts, alkylbenzenesulfonic acid salts, and alkylsurfic acid salts. The other adjuvant for formulation includes, for example, binders, dispersants, colorants and stabilizers, and specifically for example, casein, gelatin, polysaccharides (e.g., starch, gum arabic, cellulose derivatives, alginic acid) , lignin derivatives, synthetic water-soluble polymers (e.g., polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acid), PAP (isopropyl acid phosphate), BHT (2, 6-di-t-butyl-4-methylphenol) , BHA (a mixture of 2-t-butyl-4-methoxyphenol and 3-t-butyl-4- methoxyphenol) .

The method for controlling pests of the present invention is applying an effective amount of the present compound to pests directly and/or habitats of pests (e.g., plant, soil, indoor, and in-body of animals) . The present compound is usually used as the pest controlling agent of the present invention for the method for controlling pests of the present invention.

When the pest controlling agent of the present invention is used for a control of pests in agriculture, the application amount is usually 1 to 10,000 g as the present compound per 10,000 m². When the pest controlling agent of the present invention is a formulation of emulsions, wettable powders or flowables, they are usually applied after a dilution with water to have an active ingredient concentration of 0.01 to 10000 ppm. When the pest controlling agent of the present invention is a formulation of granules or powders, they are usually applied as such. These formulations and the dilute aqueous solution of the formulation may be sprayed directly to the plant to be protected from pests, and may be applied to the soil to control the pests living in a soil.

Furthermore, the resin formulations of sheets or strip form can be applied by a method such as winding around plants, stretching in the vicinity of plants and laying on the soil surface at the plant bottom.

When the pest controlling agent of the present invention is used for a control of pests in indoor, the application amount is usually 0.01 to 1000 mg as the present compound per 1 m² in case of application for plane surface, and 0.01 to 500 mg as the present compound per 1 m³ in case of application for space. When the pest controlling agent of the present invention is a formulation of emulsions, wettable powders or flowables, they are usually applied after a dilution with water to have an active ingredient concentration of 0.01 to 100,000 ppm. When the pest controlling agent of the present invention is a formulation of oil solutions, aerosols, smoking agents and poison baits, they are usually applied as such.

The pest controlling agent of the present . invention could be used in farmlands on which "crops" shown below are cultivated. "Crops"

Agricultural crops: corn, rice, wheat, barley, rye, oat, sorghum, cotton, soybean, peanut, sarrazin, sugar beet, rapeseed, sunflower, sugar cane, tobacco; Vegetables: Solanaceae vegetables (eggplant, tomato, green pepper, hot pepper, and potato) , Cucurbitaceae vegetables (cucumber, pumpkin, zucchini, watermelon, and melon ) , Cruciferae vegetables (Japanese radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, brown mustard, broccoli, and cauliflower) , Compositae vegetables (burdock, garland chrysanthemum, artichoke, and lettuce) , Liliaceae vegetables (Welsh onion, onion, garlic, and asparagus ) , Umbelliferae vegetables (carrot, parsley, celery, and parsnip) , Chenopodiaceae vegetables (spinach, and Swiss chard) , Labiatae vegetables (Japanese basil, mint, and basil) , strawberry, sweat potato, yam, aroid;

Fruit trees: pomaceous fruits (apple, common pear, Japanese pear, Chinese quince, and quince) , stone fleshy fruits (peach, plum, nectarine, Japanese plum, cherry, apricot, and prune) , citrus, plants (Satsuma mandarin, orange, lemon, lime, and grapefruit) , nuts (chestnut, walnut, hazel nut, almond, pistachio, cashew nut, and macadamia nut) , berry fruits (blueberry, cranberry, blackberry, and raspberry) , grape, persimmon, olive, loquat, banana, coffee, date, coconut palm, and oil palm;

Trees other fruit trees: tea, mulberry, flowering trees (azalea, japonica, hydrangea, sasanqua, lllicium anisatum, cherry tree, tulip poplar, crepe myetle, and orange osmanthus) , street trees (ash tree, birch, dogwood, eucalyptus, ginkgo, lilac, maple tree, oak, poplar, cercis, Chinese sweet gum, plane tree, zelkova, Japanese arborvitae, fir tree, Japanese hemlock, needle juniper, pine, spruce, yew, elm, and horse-chestnut) , sweet viburnum, Podocarpus macrophyllus, Japanese cedar, Japanese cypress, croton, spindle tree, Chainese howthorn.

Lawn: zoysia (Japanese lawn grass, mascarene grass) , Bermuda grass (Cynodon dactylon) , bent grass (creeping bent grass, Agrostis stolonifera, Agrostis tenuis) , bluegrass (Kentucky bluegrass, rough bluegrass) , fescue (tall fescue, chewing fescue, creeping fescue) , ryegrass (darnel, perennial ryegrass) , cocksfoot, timothy grass;

Others: flowers (rose, carnation, chrysanthemum, Eustoma grandiflorum Shinners (prairie gentian) , gypsophila, gerbera, pot marigold, salvia, petunia, verbena, tulip, aster, gentian, lily, pansy, cyclamen, orchid, lily of the valley, lavender, stock, ornamental kale, primula, poinsttia, gladiolus, cattleya, daisy, verbena, cymbidium, begonia) , biofuel plants ( Jatropha, curcas, safflower, Camelina alyssum, switchgrass, miscanthus, reed canary grass, Arundo donax, kenaf, cassava, willow, algae) , foliage plant .

The "crops" include genetically modified crops.

The pest controlling agents of the present invention can be a admixture with or together with other insecticides, acaricides, nematocides, fungicides, plant growth regulators, herbicides, and synergists. Examples of active ingredients of the insecticide, the acaricide, the nematocide, the fungicide, the plant growth regulator, the herbicide, and the synergist are shown below.

Active ingredients of the insecticides:

(1) Organic phosphorus compounds:

Acephate, Aluminium phosphide, butathiofos, cadusafos, chlorethoxyfos, chlorfenvinphos, chlorpyrifos, chlorpyrifos- methyl, cyanophos: CYAP, diazinon, DCIP (dichlorodiisopropyl ether) , dichlofenthion: ECP, dichlorvos (DDVP) , dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, etrimfos, fenthion: MPP, fenitrothion: MEP, fosthiazate, formothion, hydrogen phosphide, isofenphos, isoxathion, malathion, mesulfenfos, methidathion: DMTP, monocrotophos, naled: BRP, oxydeprofos: ESP, parathion, phosalone, phosmet: PMP, pirimiphos-methyl, pyridafenthion, quinalphos, phenthoate: PAP, profenofos, propaphos, prothiofos, pyraclorfos, salithion, sulprofos, tebupirimfos, temephos, tetrachlorvinphos, terbufos, thiometon, trichlorphon: DEP, vamidothion, phorate, cadusafos;

(2) Carbamate compounds:

Alanycarb, bendiocarb, benfuracarb, BPMC, carbaryl, carbofuran, carbosulfan, cloethocarb, ethiofencarb, fenobucarb, fenothiocarb, fenoxycarb, furathiocarb, isoprocarb: MIPC, metolcarb, methomyl, methiocarb, NAC, oxamyl, pirimicarb, propoxur: PHC, XMC, thiodicarb, xylylcarb, aldicarb;

(3) Pyrethroid compounds:

Acrinathrin, allethrin, benfluthrin, beta-cyfluthrin, bifenthrin, cycloprothrin, cyfluthrin, cyhalothrin, cypermethrin, deltamethrin, esfenvalerate, ethofenprox, fenpropathrin, fenvalerate, flucythrinate, flufenoprox, flumethrin, fluvalinate, halfenprox, imiprothrin, permethrin, prallethrin, pyrethrins, resmethrin, sigma- cypermethrin, silafluofen, tefluthrin, tralomethrin, transfluthrin, tetramethrin, phenothrin, cyphenothrin, alpha-cypermethrin, zeta-cypermethrin, lambda-cyhalothrin, gamma-cyhalothrin, furamethrin, tau-fluvalinate, metofluthrin, profluthrin, dimefluthrin, 2,3,5,6- tetrafluoro-4- (methoxymethyl) benzyl (EZ) - (IRS, 3RS; IRS, 3SR) - 2, 2-dimethyl-S-prop-l-enylcyclopropanecarboxylate, 2,3,5,6- tetrafluoro-4-methylbenzyl (EZ)-(IRS, 3RS; IRS, 3SR) -2,2- dimethyl-3-prop-l-enylcyclopropanecarboxylate, and 2,3,5,6- tetrafluoro-4- (methoxymethyl) benzyl (IRS, 3RS; IRS, 3SR) -2,2- dimethyl-3- (2-methyl-l-propenyl) cyclopropanecarboxylate;

(4) Nereistoxin compounds:

Cartap, bensultap, thiocyclam, monosultap, bisultap;

(5) Neonicotinoid compounds: Imidacloprid, nitenpyram, acetamiprid, thiamethoxam, thiacloprid, dinotefuran, clothianidin;

(6) Benzoylurea compounds:

Chlorfluazuron, bistrifluron, diafenthiuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron, triazuron;

(7) Phenylpyrazole compounds:

Acetoprole, ethiprole, fipronil, vaniliprole, pyriprole, pyrafluprole; ( 8 ) Bt toxins :

Live spores derived from and crystal toxins produced from Bacillus thuringiesis and a mixture thereof;

(9) Hydrazine compounds: Chromafenozide, halofenozide, methoxyfenozide, tebufenozide;

(10) Organic chlorine compounds:

Aldrin, dieldrin, dienochlor, endosulfan, methoxychlor ; (11) Other insecticidal active ingredients:

Machine oil, nicotine-sulfate; avermectin-B, bromopropylate, buprofezin, chlorphenapyr, cyantraniliprole, cyromazine, D-D (1, 3-Dichloropropene, emamectin-benzoate, fenazaquin, flupyrazofos, hydroprene, methoprene, indoxacarb, metoxadiazone, milbemycin-A, pymetrozine, pyridalyl, pyriproxyfen, spinosad, sulfluramid, tolfenpyrad, triazamate, flubendiamide, lepimectin, Arsenic acid, benclothiaz, Calcium cyanamide, Calcium polysulfide, chlordane, DDT, DSP, flufenerim, flonicamid, flurimfen, formetanate, metam-ammonium, metam-sodium, Methyl bromide, Potassium oleate, protrifenbute, spiromesifen, sulfoxaflor, Sulfur, metaflumizone, spirotetramat , pyrifluquinazone, spinetoram, chlorantraniliprole, tralopyril, cyantraniliprole, any compound represented by the following formula (K) :

wherein

R¹⁰⁰ represents chlorine, bromine or a trifluoromethyl group,

R²⁰⁰ represents chlorine, bromine or a methyl group,

R³⁰⁰ represents chlorine, bromine or a cyano group and, any compound represented by the following formula (L) :

wherein

R¹⁰⁰⁰ represents chlorine, bromine or iodide.

Active ingredients of the acardides:

Acequinocyl, amitraz, benzoximate, bifenaate, bromopropylate, chinomethionat, chlorobenzilate, CPCBS (chlorfenson) , clofentezine, cyflumetofen, dicofol, etoxazole, fenbutatin oxide, fenothiocarb, fenpyroximate, fluacrypyrim, fluproxyfen, hexythiazox, propargite: BPPS, polynactins, pyridaben, Pyrimidifen, tebufenpyrad, tetradifon, spirodiclofen, spiromesifen, sp,irotetramat , amidoflumet, cyenopyrafen. Active ingredients of the nematocides :

DCIP, fosthiazate, levamisol, methyisothiocyanate, morantel tartarate, imicyafos.

Active ingredients of the fungicides:

Azole fungicidal compounds such as propiconazole, prothioconazole, triadimenol, prochloraz, penconazole, tebuconazole, flusilazole, diniconazole, bromuconazole, epoxiconazole, difenoconazole, cyproconazole, metconazole, triflumizole, tetraconazole, myclobutanil, fenbuconazole, hexaconazole, fluquinconazole, triticonazole, bitertanol, imazalil, and flutriafol;

Cyclic amine fungicidal compouds such as fenpropimorph, tridemorph, and fenpropidin;

Benzimidazole fungicidal compounds such as carbendezim, benomyl, thiabendazole, and thiophanate-methyl;

Procymidone; cyprodinil; pyrimethanil; diethofencarb; thiuram; fluazinam; mancozeb; iprodione; vinclozolin; chlorothalonil; captan; mepanipyrim; fenpiclonil; fludioxonil; dichlofluanid; folpet; kresoxim-methyl; azoxystrobin; trifloxystrobin; fluoxastrobin; picoxystrobin; pyraclostrobin; dimoxystrobin; pyribencarb; spiroxamine; quinoxyfen; fenhexamid; famoxadone; fenamidone; zoxamide; ethaboxam; amisulbrom; iprovalicarb; benthiavalicarb) ; cyazofamid; mandipropamid; boscalid; penthiopyrad; metrafenone; fluopiran; bixafen; cyflufenamid; proquinazid; isotianil, tiadinil. Active ingredients of the herbicides: (1) Phenoxyfatty acid herbicidal compounds

2,4-PA, MCP, MCPB, phenothiol, mecoprop, fluroxypyr, triclopyr, clomeprop, and naproanilide . (2) Benzoic acid herbicidal compounds

2,3,6-TBA, dicamba, clopyralid, picloram, aminopyralid, quinclorac, and quinmerac.

(3) Urea herbicidal compounds diuron, linuron, chlortoluron, isoproturon, fluometuron, isouron, tebuthiuron, methabenzthiazuron, cumyluron, daimuron, and methyl-daimuron.

(4) Triazine herbicidal compounds atrazine, ametoryn, cyanazine, simazine, propazine, simetryn, dimethametryn, prometryn, metribuzin, indaziflam, and triaziflam.

(5) Bipyridinium herbicidal compounds paraquat, and diquat .

(6) Hydroxybenzonitrile herbicidal compounds bromoxynil and ioxynil. (7) Dinitroaniline herbicidal compounds pendimethalin, prodiamine, and trifluralin. (8) Organic phosphorus herbicidal compounds amiprofos-methyl, butamifos, bensulide, piperophos, anilofos, glyphosate, glufosinate, and bialaphos. (9) Carbamate herbicidal compounds di-allate, tri-allate, EPTC, butylate, benthiocarb, esprocarb, molinate, dimepi^'perate, swep, chlorpropham, phenmedipham, phenisopham, pyributicarb, and asulam; (10) Acid amide herbicidal compounds propanil, propyzamide, bromobutide, and etobenzanid.

(11) Chloroacetanilide herbicidal compounds acetochlor, alachlor, butachlor, dimethenamid, propachlor, metazachlor, metolachlor, pretilachlor, thenylchlor, and pethoxamid.

(12) Diphenylether herbicidal compounds acifluorfen-sodium, bifenox, oxyfluorfen, lactofen, fomesafen, chlomethoxynil, and aclonifen.

(13) Cyclic imide herbicidal compounds oxadiazon, cinidon-ethyl, carfentrazone-ethyl, surfentrazone, flumiclorac-pentyl, flumioxazin, pyraflufen- ethyl, oxadiargyl, pentoxazone, fluthiacet-methyl, butafenacil, benzfendizone, and saflufenacil .

(14) Pyrazole herbicidal compounds benzofenap, pyrazolate, pyrazoxyfen, topramezone, and pyrasulfotole.

(15) Triketone herbicidal compounds isoxaflutole, benzobicyclon, sulcotrione, mesotrione, tembotrione, and tefuryltrione. (16) Aryloxyphenoxypropionic acid herbicidal compounds clodinafop-propargyl, cyhalofop-butyl, diclofop- methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl, and -quizalofop-ethyl and metamifol.

(17) Trioneoxime herbicidal compounds alloxydim-sodium, sethoxydim, butroxydim, clethodim, cloproxydim, cycloxydim, tepraloxydim, tralkoxydim, and profoxydim.

(18) Sulfonylurea herbicidal compounds chlorsulfuron, sulfometuron-methyl, metsulfuron- methyl, chlorimuron-ethyl, tribenuron-methyl, triasulfuron, bensulfuron-methyl, thifensulfuron-methyl, pyrazosulfuron- ethyl, primisulfuron-methyl, nicosulfuron, amidosulfuron, cinosulfuron, imazosulfuron, rimsulfuron, halosulfuron- methyl, prosulfuron, ethametsulfuron-methyl, triflusulfuron- methyl, flazasulfuron, cyclosulfamuron, flupyrsulfuron, sulfosulfuron, azimsulfuron, ethoxysulfuron, oxasulfuron, iodosulfuron-methyl-sodium, foramsulfuron, mesosulfuron- methyl, trifloxysulfuron, tritosulfuron, orthosulfamuron, flucetosulfuron, and propyrisulfuron.

(19) Imidazolinone herbicidal compo.unds imazamethabenz-methyl, imazamethapyr, imazamox, imazapyr, imazaquin, and imazethapyr.

(20) Sulfonamide herbicidal compounds flumetsulam, metosulam, diclosulam, florasulam, cloransulam-methyl, penoxsulam, and pyroxsulam.

(21) Pyrimidinyloxybenzoic acid herbicidal compounds pyrithiobac-sodium, bispyribac-sodium, pyriminobac- methyl, pyribenzoxim, pyriftalid, and pyrimisulfan. (22) Other herbicidal compounds

Bentazon, bromacil, terbacil, chlorthiamid, isoxaben, dinoseb, amitrole, cinmethylin, tridiphane, dalapon, diflufenzopyr-sodium, dithiopyr, thiazopyr, flucarbazone- sodium, propoxycarbazone-sodium, mefenacet, flufenacet, fentrazamide, cafenstrole, indanofan, oxaziclomefone, benfuresate, ACN, pyridate, chloridazon, norflurazon, flurtamone, diflufenican, picolinafen, beflubutamid, clomazone, amicarbazone, pinoxaden, pyraclonil, pyroxasulfone, thiencarbazone-methyl, aminocyclopyrachlor, ipfencarbazone, and raethiozolin.

Active ingredients of the synergists: Piperonyl butoxide, sesamex, sulfoxide, N- (2- ethylhexyl) -8, 9, 10-trinorborn-5-ene-2, 3-dicarboxyimide (MGK 264), N-declyimidazole, WARF-antiresistant , TBPT, TPP, IBP, PSCP, methyl iodide (CH3I) , t-phenylbutenone, diethylmaleate, DMC, FDMC, ETP, and ETN.

Examples

The present invention will be described specifically by way of Production Examples, Formulation Examples and Test Examples but the present invention is not limited to these Examples .

First, Production Examples of the present compound are shown below. In the Production Examples, Ph represents a phenyl group.

Production Example 1

To a mixture of 7.0 g of 1, 2, 4-triazole and 100 mL of tetrahydrofuran (hereinafter referred to as THF) , 4 g of 60% sodium hydride (oily) and 14.9 g of 4, 6-dichloropyrimidine r were added under ice cooling. The mixture was stirred at room temperature for 1 hour and then stirred at 70⁰C for 6 hours. Water was poured into the reaction mixture which was cooled to room temperature, followed by extraction with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and then concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography to obtain 7.0 g of 4- chloro-6- ( [l,2,4]triazol-l-yl) -pyrimidine . 4-chloro-6- ( [1,2,4] triazol-1-yl) -pyrimidine

¹H-NMR(CDCl₃)O: 7.93(lH,s), 8.17(lH,s), 8.89(lH,s), 9.23(lH,s) .

To a mixture of 0.36 g of 2-methyl-2-propen-l-ol and 10 mli of N-methyl pyrrolidone (hereinafter referred to as NMP), 0.2 g of 60% sodium hydride (oily) and 0.91 g of 4- chloro-6- ( [1, 2, 4] triazol-1-yl) -pyrimidine were added under ice cooling. The mixture was stirred under ice cooling for 15 minutes and then stirred at room temperature for 2 hours. Water was poured into the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and then concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography to obtain 0.33 g of A- (2-methylallyloxy) -6- ( [l,2,4]triazol-l-yl) -pyrimidine . 4- (2-methylallyloxy) -6- ( [1, 2, 4] triazol-1-yl) -pyrimidine <Compound 8>

Production Example 2 To a mixture of 9.0 g of imidazolyl sodium and 100 mL of THF, 14.9 g of 4, 6-dichloropyrimidine was added under ice cooling. The mixture was stirred at room temperature for 2 hours and then stirred at 70°C for 6 hours. Water was poured into the reaction mixture which was cooled to room temperature, followed by extraction with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and then concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography to obtain 4.0 g of 4-chloro-6- (imidazol-1- yl) -pyrimidine.

4-chloro-6- (imidazol-1-yl) -pyrimidine

¹H-NMR(CDCl₃)O: 7.25-7.26 (IH, m) , 7.35-7.37 (IH, m) , 7.63- 7.65(lH,m), 8.45-8.47 (IH, m) , 8.86-8.88 (IH, m) . To a mixture of 0.36 g of 2-methyl-2-propen-l-ol and 10 mL of NMP, 0.2 g of 60% sodium hydride (oily) and 0.91 g of 4-chloro-6- (imidazol-1-yl) -pyrimidine were added under ice cooling. The mixture was stirred under ice cooling for 15 minutes and then stirred at room temperature for 2 hours. Water was poured into the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and then concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography to obtain 0.50 g of 4- (imidazol-1-yl) -6- (2-methylallyloxy) -pyrimidine .

4- (imidazol-1-yl) -6- (2-methylallyloxy) -pyrimidine <compound 29>

Production Example 3

To a mixture of 27.6 g of 1, 2, 4-triazole, 100 mL of acetonitrile and 51.7 g of N,N-diisopropylethylamine, 14.9 g of 4, 6-dichloropyrimidine was added at room temperature. The mixture was stirred at room temperature for 3 hours and then heated under reflux for 8 hours. The reaction mixture was allowed to cool and was filtered to collect a solid. This solid was washed with acetonitrile and dried to obtain 13.8 g of 4, 6-bis ( [1,2,4] triazol-1-yl) -pyrimidine. 4,6-bis( [l,2,4]triazol-l-yl) -pyrimidine

¹H-NMR(DMSO-D₆)O: 8. H(IH, d), 8.50(2H,s), 9.18(lH,d), 9.62(2H,s).

To a mixture of 0.23 g of 2, 2-dimethylpentan-3-ol and 5 mL of NMP, 0.08 g of 60% sodium hydride (oily) and 0.43 g of 4, 6-bis ( [1, 2, 4 ] triazol-1-yl) -pyrimidine were added under ice cooling. The mixture was stirred under ice cooling for 15 minutes and then stirred at room temperature for 1 hour. Water was poured into the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and then concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography to obtain 0.43 g of 4- (l-ethyl-2, 2-dimethyl-propoxy) -6- ( [1, 2, 4 ] triazol-1-yl) - pyrimidine.

4- (l-ethyl-2, 2-dimethyl-propoxy) -6- ( [1, 2, 4 ] triazol-1-yl) - pyrimidine <Compound 43>

Production Example 4

To a mixture of 7.45 g of 4, 6-dichloropyrimidine, 8.29 g of imidazole and 50 mL of acetonitrile, 6.73 g of potassium hydroxide and 1.61 g of tetrabutylammonium bromide were added at room temperature. The mixture was heated under reflux for 1 day. The reaction mixture was allowed to cool and was filtered to collect a solid. The solid was washed with water and acetonitrile and then dried to obtain 5.8 g of 4, 6-di (imidazol-1-yl) -pyrimidine. 4, 6-di (imidazol-1-yl) -pyrimidine

¹H-NMR(DMSO-D₆)O: 7.24-7.26 (2H,m) , 8.12-8.14 (2H,m) , 8.25- 8.27(lH,m), 8.76(2H,s), 9.02(lH,s) . To a mixture of 0.23 g of 2, 2-dimethylpentan-3-ol and 5 mL of NMP, 0.08 g of 60% sodium hydride (oily) and 0.42 g of 4 , 6-di (imidazol-1-yl) -pyrimidine were added under ice cooling. The mixture was stirred under ice cooling for 15 minutes and then stirred at room temperature for 1 hour. Water was poured into the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and then concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography to obtain 0.22 g of 4- (l-ethyl-2, 2-dimethyl-propoxy) -6- (imidazol-1-yl) -pyrimidine. 4- ( l-ethyl-2, 2-dimethyl-propoxy) -6- (imidazol-1-yl) - pyrimidine <Compound 44>

Production Example 5

To a mixture of 11.1 g of 1, 2, 4-triazole, 20 iriL of acetonitrile^' and 20.7 g of N,N-diisopropylethylamine, 7.34 g of 4 , 5, 6-trichloropyrimidine was added at room temperature. The mixture was stirred at room temperature for 2 hours. The reaction mixture was filtrated to collect a solid. The solid was washed with acetonitrile and then dried to obtain 8.24 g of 5-chloro-4, 6-bis ( [1, 2, 4] triazol-1-yl) -pyrimidine . 5-chloro-4, 6-bis ( [1,2,4] triazol-1-yl) -pyrimidine

1H-NMR(CDCl₃)O: 8.26(2H,s), 8.98(lH,s), 9.12(2H,s) .

To a mixture of 0.21 g of 3, 3-dimethylbutan-l-ol, 0.50 g of 5-chloro-4, 6-bis ( [1, 2, 4] triazol-1-yl) -pyrimidine and 4 mL of NMP, 0.33 g of 1, 8-diazabicyclo [5, 4, 0] 7-undecene (hereinafter, referred to as DBU) . The mixture was stirred under ice cooling for 1 hour. Water was poured into the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and then concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography to obtain 0.49 g of 5-chloro-4- (3, 3-dimethyl- butoxy) -6- ( [l,2,4]triazol-l-yl) -pyrimidine. 5-chloro-4- (3, 3-dimethy-lbutoxy) -6- ( [1,2, 4] triazol-1-yl) - pyrimidine <Compound 52>

Production Example 6

To a mixture of 2.65 g of 1, 2, 4-triazole, 10 mL of acetonitrile and 4.96 g of N, N-diisopropylethylamine, 2.61 g of 4, 6-dichloro-5-methylpyrimidine was added at room temperature. The mixture was heated under reflux for 14 hours. The reaction mixture was allowed to cool and was filtered. The filtered substance was washed with acetonitrile and then dried to obtain 2.12 g of 5-methyl- 4, 6-bis ( [1,2,4] triazol-1-yl) -pyrimidine. 5-methyl-4, 6-bis ( [1, 2, 4] triazol-1-yl) -pyrimidine

¹H-NMR(DMSO-D₆)O: 2.56(3H,s), .45(2H, s), 9. H(IH, s), 9.40 (2H,s) . To a mixture of 0.21 g of 3, 3-dimethylbutan-l-ol, 0.46 g of 5-methyl-4, 6-bis ( [1, 2, 4 ] triazol-1-yl) -pyrimidine and 3 mL of NMP, 0.33 g of DBU was added at room temperature. The mixture was stirred at room temperature for 1 day. Water was poured into the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and then concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography to obtain 0.27 g of 4- (3, 3- dimethylbutoxy) -5-methyl-6- ( [1,2,4] triazol-1-yl) -pyrimidine. 4- (3, 3-dimethyl-butoxy) -5-methyl-6- ( [1, 2, 4 ] triazol-1-yl) - pyrimidine <Compound 54>

Production Example 7

To a mixture of 7.03 g of imidazole, 30 mL of THF and

5.61 g of 4, 6-dichloro-5-methylpyrimidine, 15.7g of DBU was added room temperature. The mixture was stirred overnight.

The reaction mixture was concentrated under reduced pressure and then filtered. The solid was washed with acetonitrile and then dried to obtain 1.93 g of 4, 6-di (imidazol-1-yl) -5- methylpyrimidine .

4, 6-di (imidazol-1-yl) -5-methylpyrimidine

¹H-NMR(CDCl₃ ) O: 2.54 (3H, s) , 7.27-7.28 (2H,m) , 7.55- 7.56 (2H,m) , 8.18-8.19 (2H,m) , 8.91 (lH,s) .

To a mixture of 0.23 of 4, 6-di (imidazol-1-yl) -5- methylpyrimidine, 2 inL of NMP and 0.09 g of 2, 2-dimethyl-l- propanol, 0.04 g of 60% sodium hydride (oily) was added at room temperature. The mixture was stirred at room temperature for 1 hour. An aqueous citric acid solution was poured into the reaction mixture, followed by extraction with ethyl acetate twice. The organic layer was washed with water, dried over sodium sulfate and then concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography to obtain 0.12 g of 4- (2,2- dimethyl-1-propyloxy) -6- (imidazol-1-yl) -5-methylpyrimidine. 4- (2, 2-dimethyl-l-propyloxy) -6- (imidazol-1-yl) -5- methylpyrimidine <Compound 58>

Production Example 8

To a mixture of 0.23 g of 4, 6-di (imidazol-1-yl) -5- methylpyrimidine, 2 mL of NMP and 0.10 g of 3, 3-dimethyl-l- butanol, 0.04 g of 60% sodium hydride (oily) was added at room temperature. The mixture was stirred at room temperature for 1 hour. An aqueous citric acid solution was poured into the reaction mixture, followed by extraction twice with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and then concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography to obtain 0.16 g of 4- (3, 3- dimethyl-1-butyloxy) -6- (imidazol-1-yl) -5-methylpyrimidine . 4- (3, 3-dimethyl-l-butyloxy) -6- (imidazol-1-yl) -5- methylpyrimidine <Compound 59>

Production Example 9

A mixture of 4.56 g of 5-methyl-4, 6- bis ( [1, 2, 4 ] triazol-1-yl) -pyrimidine and 10 mL of concentrated hydrochloric acid was stirred at 70°C for 4 hours. After the reaction mixture was ice-cooled, an aqueous 10% sodium hydroxide solution was added. The precipitated crystal was collected by filtration. This crystal was dried to obtain 3.04 g of 5-methyl-6- ([1,2, 4] triazol-1-yl) -pyrimidin-4-ol .

5-methy1-6- ( [1,2, 4] triazol-1-yl) -pyrimidin-4-ol

¹H-NMR(DMSO-D₆)O: 2.17(3H,s), 8.24(lH,s), 8.31(lH,s), 9.13(lH,s), 12.94 (IH, brs) . A mixture of 2.84 g of 5-methyl-6- ( [1, 2, 4] triazol-1- yl) -pyrimidin-4-ol, 15 mL of 1,4-dioxane and 3.24 g of a Lawesson' s reagent was heated under reflux for 6 hours. The reaction mixture was allowed to cool and was filtrated to collect a solid. The solid was washed with 1,4-dioxane and then dried to obtain 2.24 g of 5-methyl-6- ( [1, 2, 4 ] triazol-1- yl) -pyrimidine-4-thiol .

5-methyl-6- ([1,2,4] triazol-1-yl) -pyrimidine-4-thiol

1H-NMR(DMSO-D₆)O: 2.41(3H,s), 8.35(lH,s), 8.38(lH,s), 9.18(lH,s), 14.52 (IH, brs) .

To a mixture of 0.19 g of 5-methyl-6- ( [1, 2, 4] triazol- 1-yl) -pyrimidine-4-thiol, 1 mL of N,N-dimethylformamide and 0.20 g of l-iodo-2, 2-dimethylpropane, 0.17 g of potassium carbonate was added under ice cooling. The mixture was stirred at 80°C for 2 hours. Water was poured into the reaction mixture, followed by extraction with ethyl acetate.

The organic layer was washed subsequently with an aqueous citric acid solution and water, dried over sodium sulfate and then concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography to obtain 0.17 g of 4- (2, 2-dimethylpropyl-l-sulfanyl) -5-methyl- 6- ( [1,2, 4] triazol-1-yl) -pyrimidine. 4- (2, 2-dimethylpropyl-l-sulfanyl) -5-methyl-6- ( [1,2, 4] triazol-1-yl) -pyrimidine <Compound 60>

The compounds produced in the same manner as in the above production method are shown in tables.

R² wherein R¹ , R² , R³ , R⁴ , R⁵ , G¹ , R⁶ and Q represent the combinations described in Table 4 to Table 6 shown below,

Table 4

Table 5

Table 6

¹H-NMR datas of the cpompounds of the present invention, whic h are described in Table 4 to Tabele 6, are shown below.

Compound 1

¹H-NMR(CDCl₃ )δ:1.05(9H,s) ,4.11(2H,s) ,7.24 (lH,d) _f 8.12 (lH,s) ,8

.63(lH,d) ,9.18(lH,s) .

Compound 2

¹H-NMR(CDCl₃ ) δ: 1.00 (9H, s) , 1.42 (9H, s) , 1.73 (2H,t) , 4.48 (2H,t) , 7

.15 (IH, d) , 8.61 (IH, d) , 9.04 (IH, s) .

Compound 3

¹H-NMR(CDCl₃ ) δ: 0.98-1.00 (6H, m) , 1.31 (3H,d) , 1.91-2.03 (lH,m) , 5. 15-5.21 ( IH, m) , 7.18 (IH, d) , 8.11 (IH, s) , 8.62 (IH, d) , 9.17 (IH, s) .

Compound 4

¹H-NMR(CDCl₃ )δ:1.03 (6H,d) ,2.06-2.20 (lH,m) , 4.21 (2H, d) , 7.22 (IH

,d) ,8.12 (IH, s) ,8.63 (IH, d) ,9.18 (IH, s) . Compound 5

¹H-NMR(CDCl₃ )δ:0.98 (3H,t) ,1.36(3H,d) , 1.63-1.85 (2H,m) ,5.22-5.

33 (lH,m) ,7.17 (IH, s) ,8.11 (IH, s) ,8.62 (IH, s) ,9.17 (IH, s) .

Compound 6

¹H-NMR(CDCl₃ ) δ: 1.07 (9H,s) ,2.49 (3H, s) , 4.12 (2H, s) , 8.14 (IH, s) , 8 .52 (IH, s) , 9.04 (IH, s) .

Compound 7

¹H-NMR(CDCl₃ ) δ:0.99(9H, s) , 1.28 (3H,d) , 5.13 (lH,q) ,7.18 (IH, s) , 8

.11 (IH, s) , 8.62 (IH, s) , 9.17 (IH, s) .

Compound 8 1H-NMR(CDCl₃ )δ:1.85(3H,s),4.88(2H,s),5.01(lH,s),5.09(lH,s),7

.27 (IH, s) ,8.12 (IH, s) ,8.65 (IH, d) ,9.18 (IH, s) .

Compound 9

¹H-NMR(CDCl₃ )δ:1.05(9H,s) ,4.11(2H,s) ,6.69(lH,d) ,7.20-7.21 (IH

,m) ,7.61-7.62 (lH,m) , 8.42 (IH, s) , 8.64 (IH, s) . Compound 10

¹H-NMR(CDCl₃ )δ:0.88 (3H,t) ,0.99 (6H,s) ,1.42 (2H,q) ,4.13 (2H,s) ,7

.23(lH,d) ,8.12 (IH, s) ,8.64 (lH,d) , 9.18 (IH, s) .

Compound 11

¹H-NMR(CDCl₃ )δ:1.05(9H,s) ,2.71 (3H,s) ,4.11(2H,s) , 6.69 (IH, s) ,7 .02(lH,d) , 7.39 ( IH, d) ,8.69 (IH, s) .

Compound 12

¹H-NMR(CDCl₃ )δ:1.04 (9H,s) ,2.29(3H,d) ,4.09(2H,s) ,6.61(lH,d) ,7

.29-7.31 ( IH, m) , 8.32-8.35 (lH,m) , 8.59-8.61 ( IH, m) .

Compound 14 ¹H-NMR(CDCl₃ )δ:1.05(9H,s) ,4.14 (2H,s) , 6.80 (IH, s) , 8.31-8.33 (IH

,m) ,8.47-8.49 (lH,m) ,8.69 (IH, s) ,9.98 (IH, s) .

Compound 15

, 1.43 ( 9H, s) , 4.10 (2H, s) , 7.20 (IH, d) , 8 .59(lH,d) ,9.05 (IH, s) .

Compound 16

¹H-NMR(CDCl₃ )δ:1.05(9H,s) ,2.70 (3H,s) ,4.14 (2H,s) ,6.73(lH,d) ,7

.94 (IH, s) ,8.72 (IH, d) .

Compound 17 1H-NMR(CDCl₃ ) δ: 1.00 (9H, s) , 1.73 (2H, t) , 4.49 (2H, t) , 6.62 (IH, d) , 7

.20-7.21 ( IH, m) , 7.59-7.60 (lH,m) , 8.40-8.41 (lH,m) , 8.65 (IH, d) .

Compound 19

¹H-NMR(CDCl₃ )δ:1.06(9H,s) ,3.28 (2H,s) ,7.71 (lH,d) ,8.12 (IH, s) ,8

.76(lH,d) , 9.19(1H, s) . Compound 20

¹H-NMR (CDCl₃ )δ:l.27 (9H, s) , 2.84 (IH, d) , 3.13 (IH, d) , 8.19 (IH, s) , 8

.62 (IH, s) ,9.06 (IH, s) ,9.28 (IH, s) .

Compound 21

¹H-NMR(CDCl₃ ) δ: 1.22 (9H, s) ,3.45 (2H, s) ,8.21 (IH, s) ,8.54-8.56 (IH ,m) , 9.20-9.22 (IH, m) ,9.28 (IH, s) .

Compound 22

¹H-NMR(CDCl₃ ) δ: l.65 (9H, s) , 7.11 (IH, s) , 8.10 (IH, s) , 8.59 (IH, s) , 9

.16 (lH, s) .

Compound 23 1H-NMR(CDCl₃ ) δ: 1.65 (9H, s) , 6.56 (IH, d) , 7.19-7.20 (lH,m) ,7.58-7.

59(lH,m) , 8.38-8.39 ( IH, m) , 8.60(lH,d) .

Compound 24

¹H-NMR(CDCl₃)OiO.99 (3H,t) , 1.48-1.50 (2H,m) , 1.77-1.82 (2H,m) , 4.

44 (2H,t) ,7.20 (IH, d) ,8.11 (IH, s) ,8.64 (IH, d) ,9.18 (IH, s) . Compound 25

¹H-NMR(CDCl₃ ) δ: 1.08 (9H, s) ,4.20 (2H, s) ,8.22 (IH, s) ,8.44 (IH, s) , 9

.07 (IH, s) .

Compound 26 1H-NMR(CDCl₃ ) δ: 1.07 (9H, s) , 4.18 (2H, s) , 7.22-7.23 (lH,m) ,7.81-7.

82 (IH, m) ,8.38 (IH, s) ,8.48 (IH, d) .

Compound 27

¹H-NMR(CDCl₃ )δ:1.04 (9H,s) ,2.62 (3H,s) ,4.07 (2H,s) ,7.04 (lH,s) ,8

.10(1H, s) ,9.18 (IH, s) . Compound 28

¹H-NMR(CDCl₃ )δ:1.04(9H,s),2.61(3H,s),4.08(2H,s),6.48(lH,s),7

.18-7.19(lH,m) , 7.60-7.61 (IH, m) ,8.41 (IH, s) .

Compound 29

¹H-NMR(CDCl₃ ) δ:l.85 (3H, s) ,4.87 (2H, s) ,5.01 (IH, s) ,5.08 (IH, s) ,6 .70-6.71 (IH, m) ,7.20-7.22 (lH,m) ,7.60-7.62 (lH,m) ,8.40-8.43 (IH, m) ,8.64-8.66(lH,m) .

Compound 30

¹H-NMR(CDCl₃ )δ:4.94-4.99(2H,m) ,5.32 (lH,d) ,5.43(lH,d) ,6.03-6.

11 ( IH, m) ,7.26 (IH, s) ,8.12 (IH, s) ,8.65 (IH, s) , 9.18 (IH, s) . Compound 31

¹H-NMR(CDCl₃ ) 5:4.95-4.98 (2H,m) , 5.30-5.36 (IH, m) ,5.40-5.47 (IH, m) ,6.02-6.14 (lH,m) , 6.69(lH,d) ,7.20-7.22 (lH,m) ,7.59-7.62 (lH,m

) ,8.42 (IH, s) ,8.64-8.66 (IH, m) .

Compound 32 1H-NMR(CDCl₃ ) δ : 0.98 ( 6H, d) ,1.66-1.74 (2H,m) , 1.75-1.86 (lH,m) ,4.

39-4.52 (2H,m) , 7.20 (IH, d) , 8.11 (IH, s) , 8.64 (IH, d) , 9.18 (IH, s) .

Compound 33

¹H-NMR(CDCl₃ ) δ:0.98 (6H,d) ,1.69 (2H,q) ,1.75-1.87 (lH,m) ,4.46 (2H

, t) , 6.64 (lH,d) ,7.19-7.22 (lH,m) ,7.59-7.61 (lH,m) , 8.41 (IH, s) , 8. 64 (IH, d) .

Compound 34

¹H-NMR(CDCl₃ )δ:1.77 (3H,d) ,4.89(2H,d) , 5.69-5.81 (IH, m) ,5.86-5.

98 (lH,m) ,7.21 (IH, s) ,8.11 (IH, s) ,8.64 (IH, s) ,9.18 (IH, s) . Compound 35

¹H-NMR(CDCl₃ )δ:1.77 (3H,d) ,4.88 (2H,d) , 5.70-5.79 (IH, m) ,5.86-5.

97 (lH,m) , 6.65 (IH, s ) ,7.20 (IH, s) , 7.58-7.60 (lH,m) ,8.40(lH,s),8.

64 (IH, s) .

Compound 36 1H-NMR(CDCl₃ ) δ : 1.80 ( 6H, d) , 4.95 (2H, d) , 5.48-5.54 ( IH, m) , 7.21 ( IH

,d) ,8.11 (IH, s) ,8.65 (IH, d) ,9.17 (IH, s) .

Compound 37

¹H-NMR(CDCl₃ ) δ:l.80 (6H,d) ,4.94 (2H,d) ,5.47-5.53 (IH, m) ,6.65 (IH

,d) ,7.19-7.21 ( IH, m) , 7.57-7.60 (lH,m) , 8.40 (IH, s) , 8.65 (IH, s) . Compound 38

¹H-NMR(CDCl₃ ) 5:2.54-2.61 (2H,m) ,4.50 (2H,t) , 5.11-5.21 (2H,m) ,5.

83-5.93 ( IH, m) , 7.22 (IH, d) , 8.11 (IH, s) , 8.64 ( IH, d) , 9.18 (IH, s) .

Compound 39

¹H-NMR(CDCl₃ ) 5:2.53-2.60 (2H,m) , 4.49 (2H, t) , 5.12-5.21 (2H,m) , 5. 82-5.93 ( IH, m) , 6.66(lH,d) , 7.19-7.22 (IH, m) , 7.59-7.61 (lH,m) ,8.4

1 (IH, s) ,8.64 (IH, d) .

Compound 40

¹H-NMR(CDCl₃ )δ:1.48 (3H,d) ,5.21 (lH,ddd) ,5.34 (lH,ddd) ,5.78-5.8

5 ( IH, m) ,5.98 (lH,ddd) , 7.21 (IH, d) , 8.11 (IH, s) , 8.63 (IH, d) , 9.17 (1 H, s) .

Compound 41

¹H-NMR(CDCl₃) δ:1.47 (3H,d) , 5.21 (IH, ddd) , 5.33 (IH, ddd) ,5.78-5.8

6 ( IH, m) ,5.97 (IH, ddd) , 6.64-6.66 ( IH, m) ,7.20-7.21 (lH,m) ,7.59-7.

60(lH,m) ,8.40-8.41(lH,m) ,8.63(lH,d) . Compound 42

¹H-NMR(CDCl₃ )δ:1.09(9H,s) ,4.19(2H,s) , 8.20 (IH, s) ,8.57 (IH, s) ,9

.03 (IH, s) .

Compound 43 1H-NMR(CDCl₃ ) δ : 0.88 ( 3H, t ) , 0.96 ( 9H, s) ,1.60-1.80 (2H,m) , 5.27-5.

33 (IH, m) ,7.19 (IH, d) ,8.12 (IH, s) ,8.59 (IH, d) , 9.18 (IH, s) .

Compound 44

¹H-NMR(CDCl₃ )δ:0.89(3H,t) ,0.96(9H,s) ,1.70-1.81 (2H,m) ,5.29-5.

34 (IH, m) , 6.64 (lH,d) ,7.20-7.22 (lH,m) , 7.61-7.63 (lH,m) ,8.42 (IH, s) ,8.59(lH,d) .

Compound 45

¹H-NMR(CDCl₃ )δ:0.90(3H,t) ,0.95(9H,s) , 1.20-1.39 (2H,m) ,1.60-1.

68 (2H,m) , 5.35-5.41 ( IH, m) , 7.18 (IH, d) , 8.12 (IH, s) , 8.59 (IH, d) , 9.

17 (IH, s) . Compound 46

¹H-NMR(CDCl₃ )δ:0.90(3H,t) ,0.96(9H,s) ,1.21-1.38 (2H,m) , 1.58-1.

66(2H,m) , 5.34-5.43 ( IH, m) ,6.62 (IH, d) ,7.20 (IH, s) ,7.60-7.62 (IH, m) ,8.41(lH,s) ,8.59(lH,s) .

Compound 47 1H-NMR(CDCl₃ )δ:1.04(9H,s),4.09(2H,s),6.21 (2H,brs) ,6.56(lH,s)

,6.74 (IH, d) , 6.91 (IH, d) ,8.59 (IH, s) .

Compound 48

¹H-NMR(CDCl₃ ) 5:0.76-1.07 (14H,m) , 1.29-1.43 (IH, m) ,1.53-1.74 (2H

,m) , 1.91-2.06 ( IH, m) , 5.34-5.46 (lH,m) , 7.17 (IH, s) , 8.11 (IH, s) , 8. 60 (IH, s) ,9.17 (IH, s) .

Compound 49

¹H-NMR(CDCl₃ ) δ: 0.89-0.99 (14H,m) , 1.33-1.40 (IH, m) , 1.54-1.71 (2H

, m) ,1.94-2.03 (IH, m) , 5.36-5.46 (IH, m) , 6.62 (IH, d) , 7.20 (IH, s) , 7.

61 (IH, s) ,8.41 (IH, s) ,8.61 (IH, d) . Compound 50

¹H-NMR(CDCl₃ ) δ: 1.09 (9H, s) , 4.18 (2H, s) , 8.20 (IH, s) , 8.58 (IH, s) , 8

.99 (1H, s) .

Compound 51 1H-NMR(CDCl₃ ) δ: 1.08 (9H, s) , 1.26 (3H, t) , 3.01 (2H, q) , 4.12 (2H, s) , 8

.13 (IH, s) ,8.51 (IH, s) , 9.05 (IH, s) .

Compound 52 '

¹H-NMR(CDCl₃ )δ:1.03(9H,s) , 1.81(2H,t) ,4.60 (2H,t) , 8.20 (IH, s) ,8

.59(1H, s) ,9.03(lH,s) . Compound 53

¹H-NMR(CDCl₃ ) δ:l.01 (3H,t) ,1.42 (3H,d) ,1.70-1.91 (2H,m) ,5.32-5.

40 (lH,m) ,8.20 (IH, s) ,8.56 (IH, s) ,9.01 (IH, s) .

Compound 54

¹H-NMR(CDCl₃ )δ:1.02 (9H,s) ,1.77 (2H,t) ,2.45 (3H,s) ,4.51 (2H,t) ,8 .13 (IH, s) ,8.53 (IH, s) , 9.03 (IH, s) .

Compound 55

¹H-NMR(CDCl₃ ) δ:0.99 (3H_f t) , 1.37 (3H,d) , 1.65-1.86 (2H,m) ,2.42-2.

45 (3H,m) , 5.26-5.35 (lH,m) , 8.13 (IH, s) , 8.51 (IH, s) , 9.02 (IH, s) .

Compound 56 1H-NMR(CDCl₃ )δ:0.86 (9H, s) ,4.08 (2H,s) , 7.18-7.20 (2H, m) ,7.39-7.

41 (3H,m) ,7.92 (IH, s) ,8.41 (IH, s) ,8.72 (IH, s) .

Compound 57

¹H-NMR(CDCl₃ )δ:0.89(9H,s) ,1.62 (2H,t) ,4.49 (2H,t) ,7.15-7.17 (2H

,m) ,7.37-7.39 (3H,m) ,7.91 (IH, s) ,8.34 (IH, s) ,8.74 (IH, s) . Compound 58

¹H-NMR(CDCl₃)0: 1.07 (9H, s) , 2.29 (3H, s) , 4.12 (2H, s) ,7.21-7.21 (IH, m) ,7.44-7.44 (lH,m) ,8.04 (IH, s) ,8.55 (IH, s) .

Compound 59

¹H-NMR(CDCl₃)O:!.02 (9H, s ) , 1.76 (2H, t) , 2.25 (3H, s) , 4.51 (2H, t) , 7. 21 (IH, s) ,7.44 (IH, s) ,8.03 (IH, s) ,8.56 (IH, s) .

Compound 60

¹H-NMR(CDCI₃)OILOS (9H, s) , 2.56 (3H, s) , 3.33 (2H, s) , 8.13 (IH, s) , 8.

68 (IH, s) ,9.02 (IH, s) . Compound 61

¹H-NMR (CDCl₃) δrl.05 (6H,d) , 2.09-2.22 (lH,m) , 2.47 (3H, s) , 4.23 (2H, d) ,8.13 (IH, s) ,8.52 (IH, s) , 9.04 (IH, s) .

Compound 62

¹H-NMR(CDCl₃)OrO.94 (3H,t) , 1.35-1.50 (4H,m) ,1.79-1.88 (2H,m) ,2.4 5-2.47 (3H,m) ,4.45(2H,t) ,8.13(lH,s) , 8.52 (lH,brs) , 9.03(lH,s) .

Compound 63

¹H-NMR(CDCl₃)O: 0.88-0.95 (3H,m) , 1.32-1.39 (4H,m) ,1.43-1.52 (2H,m

) ,1.77-1.87 (2H,m) , 2.46 (3H, brs) , 4.44 (2H, t) , 8.13 (IH, s) , 8.52 (IH

,s) , 9.03(1H, s) . Compound 64

¹H-NMR (CDCl₃)δ: L 87 (3H, s) , 2.51 (3H, s) , 4.89 (2H, s) , 5.01 (IH, brs) ,

5.10 (IH, brs) , 8.13 (IH, s) , 8.53 (IH, s) , 9.05 (IH, s) .

Compound 65

¹H-NMR (CDCl₃) δ: 2.45 (3H, s) , 2.55-2.63 (2H,m) , 4.51(2H,t) ,5.10-5.2 2 (2H,m) , 5.83-5.96 (IH, m) , 8.13 (IH, s) , 8.52 (IH, s) , 9.04 (IH, s) .

Compound 66

¹H-NMR(CDCl₃)OrL 49 (3H,d) , 2.47 (3H, s) , 5.20 (lH,dt) , 5.33 (lH,dt) ,

5.80-5.89(lH,m) , 5.95-6.05 (IH, m) , 8.13 (IH, s) , 8.51 (IH, s) , 9.03 (1

H, s) . Compound 67

¹H-NMR(CDCl₃^rO.90 (3H,t) ,1.25-1.52 (8H,m) , 1.77-1.88 (2H,m) , 2.4

6 (3H, s) ,4.44 (2H,t) ,8.13 (IH, s) ,8.52 (IH, s) , 9.03 (IH, s) .

Compound 68

¹H-NMR (CDCl₃) δr 2.49 (3H, s) , 4.99 (2H,d) , 5.32 (lH,d) , 5.44 (lH,d) , 6. 04-6.18 (lH_fm) ,8.13 (IH, s) ,8.53 (IH, s) ,9.05 (IH, s) .

Compound 69

¹H-NMR(CDCl₃) δ:0.99(3H,t) ,1.50 (2H,dd) ,1.81 (2H,dt) ,2.45 (3H, s)

, 4.45 (2H,t) ,8.12 (IH, s) ,8.51 (IH, s) , 9.03 (IH, s) .

Formulation Examples will be shown below. Parts means parts by weight.

Formulation Example 1

Ten (10) parts of each of the compounds (1) to (69) is dissolved in a mixture of 35 parts of xylene and 35 parts of

N, N-dimethylformamide, and 14 parts of polyoxyethylene styryl phenyl ether and 6 parts of calcium dodecylbenzenesulfonate are added thereto, followed by well stirring, to obtain 10% emulsions for each compound.

Formulation Example 2

Twenty (20) parts of each of the compounds (1) to (69) is added to a mixture containing 4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, 20 parts of a synthetic hydrated silicone oxide fine powder and 54 parts of diatomite, followed by well stirring, to obtain 20% wettable powders for each compound.

Formulation Example 3 To 2 parts of each of the compounds (1) to (69) are added 1 part of a synthetic hydrated silicon oxide fine powder, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65 parts of kaolin clay, followed by well stirring, and an appropriate amount of water is added to the mixture, followed by granulating with a granulator, and air drying, to give 2% granules for each compound.

Formulation Example 4 One (1) part of each of the compounds (1) to (69) is dissolved in an appropriate amount of acetone, and 5 parts of a synthetic hydrated silicon oxide fine powder, 0.3 parts of PAP, and 93.7 parts of Fubasami clay are well stirring and mixing, and acetone is removed by evaporation from the mixture, to give 1% powders for each compound.

Formulation Example 5

Ten (10) parts of each of the compounds (1) to (69), 35 parts of white carbon containing 50 parts of a polyoxyethylene alkyl ether sulfate ammonium salt, and 55 parts of water are mixed and pulverized by a wet grinding method to give 10% flowables for each compound.

Formulation Example 6 Zero point one (0.1) parts of each of the compounds (1) to (69) is dissolved in a mixture of 5 parts of xylene and 5 parts of trichloroethane, and the resulting solution is mixed with 89.9 parts of deodorized kerosine to give 0.1% oil solutions for each compound.

Formulation Example 7

Ten (10) mg of each of the compounds (1) to (69) is dissolved in 0.5 ml of acetone, the solution is applied to 5 g of powdery solid animal food (powdery solid animal food for bleeding CE-2; a product of CLEA Japan, Inc.) and mixed uniformly, and acetone is dried by evaporation from the mixture, to give poison baits for each compound.

Pest control activity of the present compound will be shown below by Test Examples. Test Example 1

The formulation of each of the present compounds (1), (3) to (7), (9), (17), (24) to (27), (30), (31), (33) to (35), (38), (39), (41), (42), (44), (46), (58), (59), (68) and (69) obtained in Formulation Example 5 was diluted with water so as to adjust the concentration of the active ingredient to 500 ppm, then a test solution was prepared.

On a cucumber seedling at 2nd true leaf stage placed in a polyethylene cup, about thirty (30) imagoes of Aphis gossypii were inoculated. One day after inoculation, 10 m of the above test solution was sprayed on the plant.

Five days after spraying, the number of the surviving insects of Aphis gossypii parasited on the leaves of the cucumber was examined and a control value was determined by the following equation.

Control value (%) = {1 - (Cb x Tai)/(Cai x Tb)) x 100 wherein symbols have the following meanings. Cb: the number of insects in a non-treated section before treatment

Cai: the number of insects in a non-treated section on observation

Tb: the number of insects in a treated-section before treatment Tai: the number of insects in a treated-section on observation

As a result, the treated section of the test solution of each of the compounds (1), (3) to (7), (9), (17), (24) to (27), (30), (31), (33) to (35), (38), (39), (41), (42),

(44), (46), (58), (59), (68) and (69) exhibited the control value of 90% or more.

Test Example 2 The formulation of each of the present compounds (1) to (3), (5) to (7), (9), (10), (15), (17) to (19), (22), (25), (26), (28), (30), (33), (34), (36), (38), (39), (41), (42), (44) to (46), (50) to (52), (54), (59), (63), (65) and (66) obtained in Reference Example 5 was diluted with water so as to adjust the concentration of the active ingredient to 500 ppm, then a test solution was prepared.

On a tomato seedling at the 3rd true leaf stage placed in a polyethylene cup, imagoes of Bemisia tabaci were released and then made to lay eggs for about 24 hours. The tomato seedling was stored in a greenhouse for 8 days. When instar larvae hatched from eggs of Bemisia tabaci, the above test solution was sprayed in the amount of 10 ml/cup. After storage in a greenhouse at 25°C for 7 days, the number of surviving instar larvae on the tomato leaves was examined and a control value was determined by the following equation.

Control value (%) = {1 - (Cb x Tai)/(Cai x Tb) } } } x 100 wherein symbols have the following meanings. Cb: the number of insects in a non-treated section before treatment

Cai: the number of insects in a non-treated section on observation Tb: the number of insects in a treated-section before treatment

Tai: the number of insects in a treated-section on observation

As a result, the treated section of the test solution of each of the compounds (1) to (3), (5) to (7), (9), (10),

(15), (17) to (19), (22), (25), (26), (28), (30), (33),

(34), (36), (38), (39), (41), (42), (44) to (46), (50) to

(52), (54), (59), (63), (65) and (66) exhibited the control value of 90% or more.

Industrial Applicability

The present compound has a control effect against pests and is useful as an active ingredient of a pest controlling agent.

Claims

1. A pyrimidine compound represented by formula (1) :

wherein

Q represents oxygen or -S(O)_n-, n represents 0, 1 or 2,

G¹ represents nitrogen or CR⁶,

R¹ , R² and R⁶ are the same or different and represent hydrogen, halogen, a nitro group, a cyano group, a chain Cl- C6 hydrocarbon group optionally substituted with halogen, - L¹R⁷, -C (=0) R⁸ , a phenyl group optionally substituted with one or more members selected from Group A, or a 5- or 6- membered aromatic heterocyclic group optionally substituted with one or more members selected from Group A, L¹ represents oxygen, -S(O)_n- or -NR⁹-,

R⁷ represents hydrogen or a chain C1-C6 hydrocarbon group optionally substituted with halogen, provided that R⁷ is not hydrogen when L¹ is -S(O)_n- and n is 1 or 2, R⁸ represents hydrogen, a hydroxy group, an amino group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C1-C6 alkoxy group optionally substituted with halogen, a C1-C4 alkylamino group optionally substituted with halogen, or a C2-C8 dialkylamino group optionally substituted with halogen, R⁹ represents hydrogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or a C1-C6 alkylsulfonyl group optionally substituted with halogen, R³ represents hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen, or -

L²R¹⁰,

R⁴ represents hydrogen, halogen, a nitro group, a cyano group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen, -L²R¹⁰, -CC=O)R¹¹, a phenyl group optionally substituted with one or more members selected from Group A, or a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more members selected from Group A,

L² represents oxygen, -S(O)_n- or -NR¹²-,

R¹⁰ represents hydrogen or a chain C1-C6 hydrocarbon group optionally substituted with halogen, provided that R¹⁰ is not hydrogen when L² is a -S(O)_n- and n is 1 or 2), R¹¹ represents hydrogen, a hydroxy group, an amino group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C1-C6 alkoxy group optionally substituted with halogen, a C1-C4 alkylamino group optionally substituted with halogen, or a C2-C8 dialkylamino group optionally substituted with halogen,

R¹² represents hydrogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or a C1-C6 alkylsulfonyl group optionally substituted with halogen, R⁵ represents a C4-C10 alkyl group or a C3-C10 alkenyl group, and

Group A represents the group consisting of halogen, an amino group, a cyano group, a nitro group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a Cl- C6 alkoxy group optionally substituted with halogen and S(O)_nR¹³, in which R¹³ represents a C1-C6 alkyl group optionally substituted with halogen.

2. The pyrimidine compound according to claim 1, wherein R¹ , R² and R⁶ are the same or different and represent hydrogen, halogen, a nitro group, a cyano group, a chain Cl- C6 hydrocarbon group optionally substituted with halogen, - L¹R⁷ or -C(=O)R⁸.

3. The pyrimidine compound according to claim 1, wherein R¹ , R² and R⁶ are the same or different and represent hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, -L¹R⁷ or -C(=O)R⁸.

4. The pyrimidine compound according to claim 1, wherein R¹ and R⁶ are the same or different and represent hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or -C(=O)R⁸.

5. The pyrimidine compound according to claim 1, wherein R² is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or -L¹R⁷.

6. The pyrimidine compound according to claim 1, wherein R⁴ is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen, or -L²R¹⁰.

7. The pyrimidine compound according to claim 1, wherein R³ is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or a C3-C8 cycloalkyl group optionally substituted with halogen.

8. The pyrimidine compound according to claim 1, wherein R³ is hydrogen.

9. The pyrimidine compound according to claim 1, wherein Q is oxygen.

10. The pyrimidine compound according to claim 1, wherein R⁵ is a branched C4-C10 alkyl group, or a C3-C10 alkenyl group.

11. The pyrimidine compound according to claim 1, wherein

Q is oxygen,

G¹ is nitrogen or CR⁶ ,

R¹ and R⁶ are the same or different and represent hydrogen, halogen, or a chain C1-C6 hydrocarbon group optionally substituted with halogen, R² is hydrogen, halogen, a chain

C1-C6 hydrocarbon group optionally substituted with halogen, or -L¹R⁷ ,

R³ is hydrogen or a chain C1-C6 hydrocarbon group optionally substituted with halogen, R⁴ is hydrogen, halogen, or a chain C1-C6 hydrocarbon group optionally substituted with halogen, and R⁵ is a branched C4-C8 alkyl group, or a C3-C8 alkenyl group.

12. A pest controlling agent comprising the pyrimidine compound according to claim 1, and an inert carrier.

13. Use of the pyrimidine compound according to claim 1 for controlling pests.

14. A method of controlling pests, which comprises a step of applying an effective amount of the pyrimidine compound according to claim 1 to pests or habitats of the pests.