JP2012036178A - Pyridine compound and pest-control usage therefor - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a novel compound that exhibits pest-control activity on harmful organism.SOLUTION: The compound is a pyrimidine compound represented by formula (1). In formula (1), J represents a group represented by formula J1 or the like; L represents a single bond or the like; A represents a single bond or the like bound to position 3 or 4 on the benzene ring in formula (1); Q represents a group represented by formula Q1 or the like; G represents a hydrogen atom or the like; m represents 0 or 1; E represents a 1-2C alkyl group or the like that may contain one or more halogen atoms; and n represents 0, 1, 2, 3 or 4.

Description

  The present invention relates to a pyrimidine compound and its use for controlling pests.

A compound having a pest control activity has been found and developed as an active ingredient of a pest control agent.
Patent Document 1 describes certain pyrimidine compounds as pharmaceuticals.

JP-A 64-25756

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

  As a result of studying to find a compound having a control activity against pests, the present inventor has found that a pyrimidine compound represented by the following formula (1) has a control effect on pests, leading to the present invention. It was.

〔式中、
Ｊは、下式Ｊ１またはＪ２

（式中、
Ｒ¹およびＲ²は、同一または相異なり、１個以上のハロゲン原子を有していてもよいＣ１−Ｃ３アルキル基を表し、
Ｒ³は、１個以上のハロゲン原子を有していてもよいＣ１−Ｃ６鎖式炭化水素基、ハロゲン原子または水素原子を表し、
Ｒ⁴およびＲ⁵は、同一または相異なり、Ｃ１−Ｃ３アルキル基を表し、
Ｒ⁶は、水素原子またはＣ１−Ｃ６鎖式炭化水素基を表す。）で示される基を表し、
Ｌは、単結合または１個以上のハロゲン原子を有していてもよいＣ１−Ｃ３アルキレン基を表し、
Ａは、上記式（１）のベンゼン環の３位または４位に結合し、単結合、−Ｏ−、または−Ｓ（Ｏ）_x−を表し（ここで、ｘは、０、１または２を表す。）、
Ｑは、下式Ｑ１、Ｑ２、Ｑ３またはＱ４

（式中、
Ｒ^xおよびＲ^yは、同一または相異なり、群αより選ばれる１個以上の原子もしくは基を有していてもよいＣ１−Ｃ６鎖式炭化水素基、シアノ基、ハロゲン原子、水素原子またはシクロプロピル基を表し、
ｙは０、１または２を表し、
Ｒ^zは、群αより選ばれる１個以上の原子もしくは基を有していてもよいＣ１−Ｃ６鎖式炭化水素基、−Ｃ（Ｏ）−Ｔ¹、−Ｓ（Ｏ）₂−Ｔ²、水素原子またはシクロプロピル基を表し、
Ｔ¹は、１個以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルキル基、１個以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルコキシ基、１個以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルキルアミノ基、１個以上のハロゲン原子を有していてもよいＣ２−Ｃ１２ジアルキルアミノ基、水酸基、アミノ基、水素原子またはシクロプロピル基を表し、
Ｔ²は、１個以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルキル基を表す。）で示される基を表し、
Ｇは、水素原子、ハロゲン原子、ニトロ基、シアノ基、水酸基、メルカプト基もしくはアミノ基を表すか、または、下式Ｇ１、Ｇ２、Ｇ３もしくはＧ４

｛式中、
Ｒ^aは、群βより選ばれる１個以上の原子もしくは基を有していてもよいＣ１−Ｃ６鎖式炭化水素基、シクロプロピル基または−Ｃ（Ｏ）−Ｔ¹を表し、
Ｒ^bは、群γより選ばれる１個以上の原子もしくは基を有していてもよいＣ１−Ｃ６鎖式炭化水素基、−Ｃ（Ｏ）−Ｔ¹、−Ｓ（Ｏ）₂−Ｔ²、Ｃ３−Ｃ９トリアルキルシリル基またはシクロプロピル基を表し、
Ｒ^cは、群γより選ばれる１個以上の原子もしくは基を有していてもよいＣ１−Ｃ６鎖式炭化水素基、−Ｃ（Ｏ）−Ｔ¹またはシクロプロピル基を表し（ここで、Ｔ¹は前述と同義であるが、ＧがＧ２、Ｇ３またはＧ４の場合には、Ｔ¹は、１個以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルキル基、１個以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルコキシ基、１個以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルキルアミノ基、１個以上のハロゲン原子を有していてもよいＣ２−Ｃ１２ジアルキルアミノ基、アミノ基、水素原子またはシクロプロピル基を表す。）、
ｚは、０、１または２を表し、
Ｒ^dは、群γより選ばれる１個以上の原子もしくは基を有していてもよいＣ１−Ｃ６鎖式炭化水素基、−Ｃ（Ｏ）−Ｔ¹、−Ｓ（Ｏ）₂−Ｔ²またはシクロプロピル基を表し（ここで、Ｔ¹およびＴ²は前述と同義である。）、
Ｒ^eは、群γより選ばれる１個以上の原子もしくは基を有していてもよいＣ１−Ｃ６鎖式炭化水素基、水素原子またはシクロプロピル基を表す。｝で示される基を表し、
ｍは０または１を表し、
Ｅは、１個以上のハロゲン原子を有していてもよいＣ１−Ｃ２アルキル基またはハロゲン原子を表し、
ｎは０、１、２、３または４を表し、
但し、ｎが２、３または４の場合は、各々のＥは互いに異なっていてもよい。
群α：ハロゲン原子、シアノ基およびシクロプロピル基からなる群。
群β：１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４アルコキシ基、１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４アルキルチオ基、１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４アルキルスルフィニル基、１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４アルキルスルホニル基、１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４アルキルアミノ基、１個以上のハロゲン原子を有していてもよいＣ２−Ｃ８ジアルキルアミノ基、ハロゲン原子、シアノ基、Ｃ３−Ｃ９トリアルキルシリル基およびシクロプロピル基からなる群。
群γ：１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４アルコキシ基、１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４アルキルチオ基、１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４アルキルスルフィニル基、１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４アルキルスルホニル基、１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４アルキルアミノ基、１個以上のハロゲン原子を有していてもよいＣ２−Ｃ８ジアルキルアミノ基、フェニル基（該フェニル基は、メチル基、メトキシ基、塩素原子またはニトロ基を有していてもよい。）、ハロゲン原子、シアノ基、Ｃ３−Ｃ９トリアルキルシリル基およびシクロプロピル基からなる群。
但し、ＱがＱ４であり、Ｒ^zが水素原子であり、Ｇが水素原子であり、ｎが０であり、Ａ基の置換位置がベンゼン環の４位であり、Ａが単結合であり、ＪがＪ１であり、Ｒ¹およびＲ²がいずれもエチル基であり、かつ、Ｒ³が水素原子である場合には、Ｌは、単結合またはＣ１−Ｃ３アルキレン基を表す。〕
で示されるピリミジン化合物。（以下、本発明化合物と記す。）。
［発明２］ ＱがＱ１である［発明１］記載のピリミジン化合物。
［発明３］ ＱがＱ２、Ｑ３またはＱ４である［発明１］記載のピリミジン化合物。
［発明４］ ＱがＱ２である［発明１］記載のピリミジン化合物。
［発明５］ ＱがＱ３である［発明１］記載のピリミジン化合物。
［発明６］ ＱがＱ４である［発明１］記載のピリミジン化合物。
［発明７］ Ｌが、単結合またはＣ１−Ｃ３アルキレン基である［発明１］記載のピリミジン化合物。
［発明８］ Ｇが、水素原子、ハロゲン原子、Ｇ１、Ｇ２、Ｇ３またはＧ４である［発明１］記載のピリミジン化合物。
［発明９］ Ｇが、Ｇ１、Ｇ２、Ｇ３またはＧ４である［発明１］記載のピリミジン化合物。
［発明１０］ Ｇが、Ｇ２またはＧ３である［発明１］記載のピリミジン化合物。
［発明１１］ Ｇが、Ｇ１またはＧ４である［発明１］記載のピリミジン化合物。
［発明１２］ ［発明１］〜［発明１１］いずれか一項記載のピリミジン化合物と不活性担体とを含有する有害生物防除剤。
［発明１３］ 有害生物を防除するための［発明１］〜［発明１１］いずれか一項記載のピリミジン化合物の使用。
［発明１４］ ［発明１］〜［発明１１］いずれか一項記載のピリミジン化合物の有効量を有害生物又は有害生物の生息場所に施用する工程を含む有害生物の防除方法。 That is, the present invention is as follows.
[Invention 1] Formula (1)

[Where,
J is the following formula J1 or J2

(Where
R ¹ and R ² are the same or different and each represents a C1-C3 alkyl group optionally having one or more halogen atoms,
R ³ represents a C1-C6 chain hydrocarbon group which may have one or more halogen atoms, a halogen atom or a hydrogen atom,
R ⁴ and R ⁵ are the same or different and represent a C1-C3 alkyl group,
R ⁶ represents a hydrogen atom or a C1-C6 chain hydrocarbon group. ) Represents a group represented by
L represents a single bond or a C1-C3 alkylene group which may have one or more halogen atoms,
A is bonded to the 3-position or 4-position of the benzene ring of the formula (1) and represents a single bond, —O—, or —S (O) _x — (where x is 0, 1 or 2). Represents)
Q is the following formula Q1, Q2, Q3 or Q4

(Where
R ^x and R ^y are the same or different and each may have one or more atoms or groups selected from group α, a C1-C6 chain hydrocarbon group, cyano group, halogen atom, hydrogen atom or cyclo Represents a propyl group,
y represents 0, 1 or 2;
R ^z is a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from the group α, —C (O) —T ¹ , —S (O) ₂ —T ^2. Represents a hydrogen atom or a cyclopropyl group,
T ¹ has a C1-C6 alkyl group optionally having one or more halogen atoms, a C1-C6 alkoxy group optionally having one or more halogen atoms, and having one or more halogen atoms. An optionally substituted C1-C6 alkylamino group, an optionally substituted C2-C12 dialkylamino group, a hydroxyl group, an amino group, a hydrogen atom or a cyclopropyl group,
T ² represents a C1-C6 alkyl group which may have one or more halogen atoms. ) Represents a group represented by
G represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a mercapto group or an amino group, or G 1, G 2, G 3 or G 4

{Where,
R ^a represents a C1-C6 chain hydrocarbon group, a cyclopropyl group or —C (O) —T ¹ which may have one or more atoms or groups selected from the group β,
R ^b is a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from the group γ, —C (O) —T ¹ , —S (O) ₂ —T ^2. Represents a C3-C9 trialkylsilyl group or a cyclopropyl group,
R ^c represents a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from the group γ, —C (O) —T ¹ or a cyclopropyl group (where, T ¹ is as defined above, but when G is G2, G3 or G4, T ¹ is a C1-C6 alkyl group optionally having one or more halogen atoms, one or more halogens. C1-C6 alkoxy group which may have an atom, C1-C6 alkylamino group which may have one or more halogen atoms, C2-C12 which may have one or more halogen atoms A dialkylamino group, an amino group, a hydrogen atom or a cyclopropyl group).
z represents 0, 1 or 2;
R ^d is a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from the group γ, —C (O) —T ¹ , —S (O) ₂ —T ^2. Or a cyclopropyl group (wherein T ¹ and T ² are as defined above),
R ^e represents a C1-C6 chain hydrocarbon group, a hydrogen atom or a cyclopropyl group which may have one or more atoms or groups selected from the group γ. } Represents a group represented by
m represents 0 or 1;
E represents a C1-C2 alkyl group which may have one or more halogen atoms or a halogen atom,
n represents 0, 1, 2, 3 or 4;
However, when n is 2, 3 or 4, each E may be different from each other.
Group α: a group consisting of a halogen atom, a cyano group and a cyclopropyl group.
Group β: C1-C4 alkoxy group optionally having one or more halogen atoms, C1-C4 alkylthio group optionally having one or more halogen atoms, having one or more halogen atoms C1-C4 alkylsulfinyl group which may have one, C1-C4 alkylsulfonyl group which may have one or more halogen atoms, C1-C4 alkylamino group which may have one or more halogen atoms A group consisting of a C2-C8 dialkylamino group optionally having one or more halogen atoms, a halogen atom, a cyano group, a C3-C9 trialkylsilyl group and a cyclopropyl group.
Group γ: C1-C4 alkoxy group optionally having one or more halogen atoms, C1-C4 alkylthio group optionally having one or more halogen atoms, having one or more halogen atoms C1-C4 alkylsulfinyl group which may have one, C1-C4 alkylsulfonyl group which may have one or more halogen atoms, C1-C4 alkylamino group which may have one or more halogen atoms A C2-C8 dialkylamino group or a phenyl group which may have one or more halogen atoms (the phenyl group may have a methyl group, a methoxy group, a chlorine atom or a nitro group), A group consisting of a halogen atom, a cyano group, a C3-C9 trialkylsilyl group and a cyclopropyl group.
However, Q is Q4, ^Rz is a hydrogen atom, G is a hydrogen atom, n is 0, the substitution position of the A group is the 4-position of the benzene ring, A is a single bond, When J is J1, R ¹ and R ² are both ethyl groups, and R ³ is a hydrogen atom, L represents a single bond or a C1-C3 alkylene group. ]
The pyrimidine compound shown by these. (Hereinafter referred to as the present compound).
[Invention 2] The pyrimidine compound according to [Invention 1], wherein Q is Q1.
[Invention 3] The pyrimidine compound according to [Invention 1], wherein Q is Q2, Q3 or Q4.
[Invention 4] The pyrimidine compound according to [Invention 1], wherein Q is Q2.
[Invention 5] The pyrimidine compound according to [Invention 1], wherein Q is Q3.
[Invention 6] The pyrimidine compound according to [Invention 1], wherein Q is Q4.
[Invention 7] The pyrimidine compound according to [Invention 1], wherein L is a single bond or a C1-C3 alkylene group.
[Invention 8] The pyrimidine compound according to [Invention 1], wherein G is a hydrogen atom, a halogen atom, G1, G2, G3 or G4.
[Invention 9] The pyrimidine compound according to [Invention 1], wherein G is G1, G2, G3 or G4.
[Invention 10] The pyrimidine compound according to [Invention 1], wherein G is G2 or G3.
[Invention 11] The pyrimidine compound according to [Invention 1], wherein G is G1 or G4.
[Invention 12] A pest control agent comprising the pyrimidine compound according to any one of [Invention 1] to [Invention 11] and an inert carrier.
[Invention 13] Use of the pyrimidine compound according to any one of [Invention 1] to [Invention 11] for controlling pests.
[Invention 14] A method for controlling pests comprising a step of applying an effective amount of the pyrimidine compound according to any one of [Invention 1] to [Invention 11] to a pest or a habitat of the pest.

  Examples of substituents used in the description of the present specification will be described below.

  In the compound of the present invention, “halogen atom” means a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

Examples of the “C1-C2 alkyl group optionally having one or more halogen atoms” in the compound of the present invention include a methyl group, an ethyl group, and a trifluoromethyl group.

Examples of the “C1-C3 alkyl group” in the compound of the present invention include a methyl group, an ethyl group, a propyl group, and an isopropyl group.

Examples of the “C1-C3 alkyl group optionally having one or more halogen atoms” in the compound of the present invention include a methyl group, an ethyl group, a propyl group, an isopropyl group, and a trifluoromethyl group.

Examples of the “C1-C6 alkyl group optionally having one or more halogen atoms” in the compound of the present invention include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, and a sec-butyl group. , Tert-butyl group, pentyl group, hexyl group and trifluoromethyl group.

In the compound of the present invention, examples of the “C1-C6 chain hydrocarbon group” include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, 2 , C1-C6 alkyl groups such as 2-dimethylpropyl group, 3-methylbutyl group, 2,3-dimethylbutyl group, 3,3-dimethylbutyl group and hexyl group;
Vinyl group, 1-propenyl group, 2-propenyl group, isopropenyl group, 2-methyl-1-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group and 1-hexenyl group C2-C6 alkenyl groups such as ethynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 3,3-dimethyl-1-butynyl, 1-pentynyl and 1-hexynyl C2-C6 alkynyl groups such as

Examples of the “C1-C6 chain hydrocarbon group optionally having one or more halogen atoms” in the compound of the present invention include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, sec 1 such as -butyl group, tert-butyl group, pentyl group, 2,2-dimethylpropyl group, 3-methylbutyl group, 2,3-dimethylbutyl group, 3,3-dimethylbutyl group hexyl group and trifluoromethyl group A C1-C6 alkyl group optionally having one or more halogen atoms;
Vinyl group, 1-propenyl group, 2-propenyl group, isopropenyl group, 2-methyl-1-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group and 1-hexenyl group A C2-C6 alkenyl group optionally having one or more halogen atoms such as a C2-C6 alkenyl group such as 2,2-difluorovinyl group, etc .; and an ethynyl group, a propargyl group, a 1-butynyl group, 2- C2 which may have one or more halogen atoms such as butynyl group, 3-butynyl group, 3,3-dimethyl-1-butynyl group, 1-pentynyl group, 1-hexynyl group and 2-chloroethynyl group -C6 alkynyl group is mentioned.

In the compound of the present invention, examples of the “C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from group α” include, for example, methyl group, ethyl group, propyl group, isopropyl group, butyl One or more atoms selected from the group α such as a group, isobutyl group, sec-butyl group, tert-butyl group, trifluoromethyl group, 2,2,2-trifluoroethyl group, cyanomethyl group and cyclopropylmethyl group Or a C1-C6 alkyl group which may have a group;
A C2-C6 alkenyl group optionally having one or more atoms or groups selected from group α such as 2-propenyl group; and one or more selected from group α such as propargyl group and 2-butynyl group The C2-C6 alkynyl group which may have an atom or group is mentioned.

Examples of the “C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from group β” in the compounds of the present invention include a methyl group, an ethyl group, a propyl group, an isopropyl group, and butyl. Groups, isobutyl groups, sec-butyl groups, C1-C6 alkyl groups such as tert-butyl groups;
C1-C6 alkyl having one or more atoms or groups selected from the group β such as trifluoromethyl group, cyanomethyl group, cyclopropylmethyl group, methoxymethyl group, ethoxymethyl group, 1-methoxyethyl group and methylthiomethyl group Group;
One or more atoms or groups selected from the group β such as vinyl group, isopropenyl group, 1-propenyl group, 2-methyl-1-propenyl group, 2,2-dichlorovinyl group, and 2,2-difluorovinyl group A C2-C6 alkenyl group optionally having one of the following: and one selected from the group β such as an ethynyl group, a 1-propynyl group, a 2-chloroethynyl group, a 2-fluoroethynyl group and a 2- (trimethylsilyl) ethynyl group The C2-C6 alkynyl group which may have the above atoms or groups is mentioned.

In the compound of the present invention, examples of the “C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from group γ” include a methyl group, an ethyl group, a propyl group, an isopropyl group, and butyl. Groups, C1-C6 alkyl groups such as isobutyl group, sec-butyl group and tert-butyl group;
Difluoromethyl group, trifluoromethyl group, 2-fluoroethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, 1,1,1-trifluoro-2-propyl group, cyanomethyl group 1-cyanoethyl group, cyclopropylmethyl group, 1- (cyclopropyl) ethyl group, methoxymethyl group, ethoxymethyl group, 1-methoxyethyl group, 2-methoxyethyl group, methylthiomethyl group, methylsulfinylmethyl group, methyl Sulfonylmethyl group, 2- (methylthio) ethyl group, 2- (methylsulfinyl) ethyl group, 2- (methylsulfonyl) ethyl group, 2- (methylamino) ethyl group, 2- (dimethylamino) ethyl group, benzyl group 4-methoxybenzyl group, 3,4-dimethoxybenzyl group, 4-nitrobenzyl group, etc. C1-C6 alkyl group having one or more atoms or groups selected from the group gamma;
A C3-C6 alkenyl group optionally having one or more atoms or groups selected from the group γ such as 2-propenyl group, 2-butenyl group and 3-methyl-2-butenyl group; and a propargyl group, 2 -C2-C6 alkynyl group which may have one or more atoms or groups selected from group γ such as -butynyl group and 3-butynyl group.

Examples of the “C1-C3 alkylene group optionally having one or more halogen atoms” in the compound of the present invention include —CH ₂ —, —CHCl—, —CHF—, —CF ₂ —, —CH ₂ CH. ₂ - and -CH ₂ CH ₂ CH ₂ - and the like.

In the compound of the present invention, “C3-C9 trialkylsilyl group” means a trialkylsilyl group having 3 to 9 carbon atoms in the alkyl portion, and each alkyl group may be the same or different. Examples thereof include a tert-butyldimethylsilyl group, a triethylsilyl group, an isopropyldimethylsilyl group, and a triisopropylsilyl group.

Examples of the “C1-C6 alkoxy group optionally having one or more halogen atoms” in the compounds of the present invention include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, and a sec-butoxy group. Group, tert-butoxy group, 2,2,2-trichloroethoxy group and 2,2,2-trifluoroethoxy group.

Examples of the “C1-C6 alkylamino group optionally having one or more halogen atoms” in the compound of the present invention include a methylamino group, an ethylamino group, a propylamino group, an isopropylamino group, a butylamino group, and an isobutyl group. Examples thereof include an amino group, a sec-butylamino group, a tert-butylamino group, and a 2,2,2-trifluoroethylamino group.

In the compound of the present invention, the “C2-C12 dialkylamino group optionally having one or more halogen atoms” has one or more halogen atoms in which the total number of carbons in the alkyl moiety is 2 to 12. Each alkyl group may be the same or different, for example, N, N-dimethylamino group, N, N-diethylamino group, N, N-dipropylamino group, N, N- Dibutylamino group, N-ethyl-N-methylamino group, N-methyl-N-propylamino group, N-isopropyl-N-methylamino group, N-tert-butyl-N-methylamino group and N-methyl- N-2,2,2-trifluoroethylamino group may be mentioned.

As the “C1-C4 alkoxy group optionally having one or more halogen atoms” in the present compound,
Examples thereof include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, a sec-butoxy group, a tert-butoxy group, and a 2,2,2-trifluoroethoxy group.

In the compound of the present invention, “C1-C4 alkylthio group optionally having one or more halogen atoms”
Examples thereof include a methylthio group, an ethylthio group, a propylthio group, an isopropylthio group, a butylthio group, an isobutylthio group, a sec-butylthio group, a tert-butylthio group, and a 2,2,2-trifluoroethylthio group.

In the compound of the present invention, “C1-C4 alkylsulfinyl group optionally having one or more halogen atoms”
Examples include methylsulfinyl group, ethylsulfinyl group, propylsulfinyl group, isopropylsulfinyl group, butylsulfinyl group, isobutylsulfinyl group, sec-butylsulfinyl group, tert-butylsulfinyl group, and 2,2,2-trifluoroethylsulfinyl group. It is done.

As the “C1-C4 alkylsulfonyl group optionally having one or more halogen atoms” in the present compound,
Examples include methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group, isopropylsulfonyl group, butylsulfonyl group, isobutylsulfonyl group, sec-butylsulfonyl group, tert-butylsulfonyl group and 2,2,2-trifluoroethylsulfonyl group. It is done.

In the compound of the present invention, “C1-C4 alkylamino group optionally having one or more halogen atoms”
Examples include methylamino group, ethylamino group, propylamino group, isopropylamino group, butylamino group, isobutylamino group, sec-butylamino group, tert-butylamino group and 2,2,2-trifluoroethylamino group. It is done.

In the compound of the present invention, the “C2-C8 dialkylamino group optionally having one or more halogen atoms” has one or more halogen atoms having 2 to 8 carbon atoms in the alkyl part. Each alkyl group may be the same or different, for example, N, N-dimethylamino group, N, N-diethylamino group, N, N-dipropylamino group, N, N- Dibutylamino group, N-ethyl-N-methylamino group, N-methyl-N-propylamino group, N-isopropyl-N-methylamino group, N-tert-butyl-N-methylamino group, N-tert- Examples thereof include a butyl-N-methylamino group and an N-methyl-N-2,2,2-trifluoroethylamino group.

In the compound of the present invention, “phenyl group (which may have a methyl group, a methoxy group, a chlorine atom or a nitro group”) means a group consisting of a methyl group, a methoxy group, a chlorine atom and a nitro group. Represents a phenyl group which may be substituted with one or more substituents independently selected from, for example, phenyl group, 4-methoxyphenyl group, 3,4-dimethoxyphenyl group, 4-nitrophenyl group 2-nitrophenyl group, 4-chlorophenyl group, 2-chlorophenyl group, 2,6-dichlorophenyl group and 4-methylphenyl group.

Examples of the compound of the present invention include the following pyrimidine compounds.
In the formula (1), a compound in which Q and G are a combination of [Table 1] to [Table 6] (Aspect 1 to Aspect 138). In addition, for example, the aspect 1 is “a pyrimidine compound in which Q is Q1, Q2, Q3 or Q4 and G is a hydrogen atom, a halogen atom, G1, G2, G3 or G4 in the formula (1)”. To express.

Moreover, as this invention compound, the following pyrimidine compounds are also mentioned, for example.
In the formula (1), L is a single bond or —CH ₂ —, A is a single bond or —O—, and J is J1 or J2. [Invention 1] to [Invention 6], [Invention 8] ] To [Invention 11] and the pyrimidine compound according to any one of Embodiments 1 to 138;
In Formula (1), L is a single bond or —CH ₂ —, A is a single bond or —O—, and J is J1 (when J is J1, R ¹ and R ² are both methyl groups. And R ³ is a hydrogen atom, a methyl group, or an ethyl group.) Or J2 (when J is J2, R ⁴ , R ^5, and R ⁶ are all methyl groups). Invention 1] to [Invention 6], [Invention 8] to [Invention 11] and a pyrimidine compound according to any one of Embodiments 1 to 138;
In formula (1), L is a single bond, A is a single bond, J is J1 (when J is J1, R ¹ and R ² are both methyl groups, R ³ is a hydrogen atom, [Invention 1] to [Invention 6], which is a methyl group or an ethyl group) or J2 (when J is J2, R ⁴ , R ⁵ and R ⁶ are all methyl groups). [Invention 8] to [Invention 11] and a pyrimidine compound according to any one of Embodiments 1 to 138;
[Invention 1] to [Invention 6], [Invention 8] to [Invention 11] and Aspect 1 to Aspect 138, wherein J-LA is a tert-butyl group in Formula (1). Pyrimidine compounds;

In the formula (1), Q is Q1, and R ^x and R ^y may be the same or different and may have one or more atoms or groups selected from the group α, A group or a hydrogen atom,
Q is Q2 or
Q is Q3 or
[Invention 1], [Invention], wherein Q is Q4 and R ^z is a C1-C6 chain hydrocarbon group or hydrogen atom optionally having one or more atoms or groups selected from group α 7] to [Invention 11] and the pyrimidine compound according to any one of Embodiments 1 to 23;
In the formula (1), Q is Q1, and R ^x and R ^y are the same or different and are a methyl group or a hydrogen atom,
Q is Q2 or
Q is Q3 and y is 0, or
The pyrimidine compound according to any one of [Invention 1], [Invention 7] to [Invention 11] and Embodiments 1 to 23, wherein Q is Q4 and R ^z is a methyl group or a hydrogen atom;

In the formula (1), Q is Q1, and R ^x and R ^y may be the same or different and may have one or more atoms or groups selected from the group α, The pyrimidine compound according to any one of [Invention 2] and Embodiments 24 to 46, which is a group or a hydrogen atom;
In Formula (1), Q is Q1, and R ^x and R ^y are the same or different and are a methyl group or a hydrogen atom [Invention 2] and a pyrimidine compound according to any one of Embodiments 24 to 46;

In the formula (1), Q is Q2 or
Q is Q3 or
Q is Q4, and R ^z is a C1-C6 chain hydrocarbon group or hydrogen atom optionally having one or more atoms or groups selected from group α [Invention 3] and Embodiment 47 The pyrimidine compound according to any one of to 69.
In the formula (1), Q is Q2 or
Q is Q3 and y is 0, or
The pyrimidine compound according to any one of [Invention 3] and Embodiments 47 to 69, wherein Q is Q4 and R ^z is a methyl group or a hydrogen atom;

In Formula (1), Q is Q3, and y is 0 [Invention 5] and a pyrimidine compound according to any one of Embodiments 93 to 115;

In the formula (1), Q is Q4, and R ^z is a C1-C6 chain hydrocarbon group or hydrogen atom which may have one or more atoms or groups selected from the group α [ Invention 6] and a pyrimidine compound according to any one of Embodiments 116 to 138;
In Formula (1), Q is Q4, and R ^z is a methyl group or a hydrogen atom [Invention 6] and a pyrimidine compound according to any of Embodiments 116 to 138;

In the formula (1), G is a hydrogen atom or a halogen atom,
G is G1 and R ^a is ^a C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from group β,
G is G2 and R ^b is a C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from group γ,
G is G3, and R ^c is a C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from group γ, or
G is G4, R ^d is a C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from group γ, and R ^e is selected from group γ The pyrimidine compound according to any one of [Invention 1] to [Invention 7], which is a C1-C6 chain hydrocarbon group which may have one or more atoms or groups, or a hydrogen atom;
In Formula (1), G is a halogen atom,
G is G1 and R ^a is ^a C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from group β,
G is G2 and R ^b is a C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from group γ,
G is G3, and R ^c is a C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from group γ, or
G is G4, R ^d is a C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from group γ, and R ^e is selected from group γ The pyrimidine compound according to any one of [Invention 1] to [Invention 7], which is a C1-C6 chain hydrocarbon group which may have one or more atoms or groups, or a hydrogen atom;

In Formula (1), G is G1, and R ^a is ^a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from group β,
G is G2 and R ^b is a C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from group γ,
G is G3, and R ^c is a C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from group γ, or
G is G4, R ^d is a C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from group γ, and R ^e is selected from group γ The pyrimidine compound according to any one of [Invention 1] to [Invention 7], which is a C1-C6 chain hydrocarbon group which may have one or more atoms or groups, or a hydrogen atom;

In the formula (1), G is a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, a methyl group, an ethyl group, a propyl group, an isopropyl group, a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, 2,2, 2-trifluoroethoxy group, methylthio group, ethylthio group, propylthio group, isopropylthio group, 2,2,2-trifluoroethylthio group, N, N-dimethylamino group, N, N-diethylamino group, N, N -Dipropylamino group, N-ethyl-N-methylamino group, N-methyl-N-propylamino group, N-isopropyl-N-methylamino group, N-methyl-N- (2,2,2-tri Fluoroethyl) amino group, N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group or N- (2,2,2-tri Ruoroechiru) an amino group [Invention 1] to pyrimidine compound according to any one of [Invention 7];
In the formula (1), G is a fluorine atom, a chlorine atom, a bromine atom, a methyl group, an ethyl group, a propyl group, an isopropyl group, a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, 2,2,2-tri Fluoroethoxy group, methylthio group, ethylthio group, propylthio group, isopropylthio group, 2,2,2-trifluoroethylthio group, N, N-dimethylamino group, N, N-diethylamino group, N, N-dipropyl Amino group, N-ethyl-N-methylamino group, N-methyl-N-propylamino group, N-isopropyl-N-methylamino group, N-methyl-N- (2,2,2-trifluoroethyl) Amino group, N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group or N- (2,2,2-trifluoroethyl) Le) is an amino group [Invention 1] to pyrimidine compound according to any one of [Invention 7];
In the formula (1), G is methyl group, ethyl group, propyl group, isopropyl group, methoxy group, ethoxy group, propoxy group, isopropoxy group, 2,2,2-trifluoroethoxy group, methylthio group, ethylthio group , Propylthio group, isopropylthio group, 2,2,2-trifluoroethylthio group, N, N-dimethylamino group, N, N-diethylamino group, N, N-dipropylamino group, N-ethyl-N- Methylamino group, N-methyl-N-propylamino group, N-isopropyl-N-methylamino group, N-methyl-N- (2,2,2-trifluoroethyl) amino group, N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, or N- (2,2,2-trifluoroethyl) amino group [Invention 1] to [Invention] Pyrimidine compound according to any one of 7];

In the formula (1), G is G2, and R ^b is a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from the group γ, or G Any one of [Invention 1] to [Invention 7], wherein R is G3, and R ^c is a C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from group γ A pyrimidine compound according to claim 1;
In the formula (1), G represents methoxy group, ethoxy group, propoxy group, isopropoxy group, 2,2,2-trifluoroethoxy group, methylthio group, ethylthio group, propylthio group, isopropylthio group, or 2,2, The pyrimidine compound according to any one of [Invention 1] to [Invention 7], which is a 2-trifluoroethylthio group;
In the formula (1), G is G1, and R ^a is ^a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from the group β, or
G is G4, R ^d is a C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from group γ, and R ^e is selected from group γ The pyrimidine compound according to any one of [Invention 1] to [Invention 7], which is a C1-C6 chain hydrocarbon group which may have one or more atoms or groups, or a hydrogen atom;
In the formula (1), G is methyl group, ethyl group, propyl group, isopropyl group, N, N-dimethylamino group, N, N-diethylamino group, N, N-dipropylamino group, N-ethyl-N. -Methylamino group, N-methyl-N-propylamino group, N-isopropyl-N-methylamino group, N-methyl-N- (2,2,2-trifluoroethyl) amino group, N-methylamino group , N-ethylamino group, N-propylamino group, N-isopropylamino group, or N- (2,2,2-trifluoroethyl) amino group, [Invention 1] to [Invention 7] Pyrimidine compounds of
In Formula (1), G is G1, and R ^a is ^a C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from group β [Invention 1] To [Invention 7] pyrimidine compound according to any one of the above;
The pyrimidine compound according to any one of [Invention 1] to [Invention 7], wherein, in Formula (1), G is a methyl group, an ethyl group, a propyl group, or an isopropyl group;
In the formula (1), G is G2, and R ^b is a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from the group γ [Invention 1] To [Invention 7] pyrimidine compound according to any one of the above;
The pyrimidine according to any one of [Invention 1] to [Invention 7], wherein, in the formula (1), G is a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group or a 2,2,2-trifluoroethoxy group. Compound;

In the formula (1), G is G3, and R ^c is a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from the group γ [Invention 1] To [Invention 7] pyrimidine compound according to any one of the above;
In the formula (1), G is a methylthio group, an ethylthio group, a propylthio group, an isopropylthio group, or a 2,2,2-trifluoroethylthio group, according to any one of [Invention 1] to [Invention 7]. Pyrimidine compounds;
In the formula (1), G is G4, R ^d is a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from the group γ, and R ^e is The pyrimidine compound according to any one of [Invention 1] to [Invention 7], which is a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from group γ, or a hydrogen atom ;
In the formula (1), G represents N, N-dimethylamino group, N, N-diethylamino group, N, N-dipropylamino group, N-ethyl-N-methylamino group, N-methyl-N-propyl. Amino group, N-isopropyl-N-methylamino group, N-methyl-N- (2,2,2-trifluoroethyl) amino group, N-methylamino group, N-ethylamino group, N-propylamino group The pyrimidine compound according to any one of [Invention 1] to [Invention 7], which is an N-isopropylamino group or an N- (2,2,2-trifluoroethyl) amino group.

Moreover, as this invention compound, the following pyridine compounds are also mentioned, for example.

In equation (1),
L is a single bond or —CH ₂ —, A is a single bond or —O—, J is J1 (when J is J1, R ¹ and R ² are both methyl groups, and R ³ is A hydrogen atom, a methyl group or an ethyl group) or J2 (when J is J2, R ⁴ , R ⁵ and R ⁶ are all methyl groups);
Q is Q1, and R ^x and R ^y are the same or different, and are a methyl group or a hydrogen atom, Q is Q2, Q is Q3, and y is 0, or , Q is Q4, and R ^z is a methyl group or a hydrogen atom,
G is methyl, ethyl, propyl, isopropyl, methoxy, ethoxy, propoxy, isopropoxy, 2,2,2-trifluoroethoxy, methylthio, ethylthio, propylthio, isopropylthio Group, 2,2,2-trifluoroethylthio group, N, N-dimethylamino group, N, N-diethylamino group, N, N-dipropylamino group, N-ethyl-N-methylamino group, N- Methyl-N-propylamino group, N-isopropyl-N-methylamino group, N-methyl-N- (2,2,2-trifluoroethyl) amino group, N-methylamino group, N-ethylamino group, The pyrimidine compound according to [Invention 1], which is an N-propylamino group, an N-isopropylamino group or an N- (2,2,2-trifluoroethyl) amino group

〔式中、
Ｑ^zは、−ＣＨ₂−、−ＣＨ（ＣＨ₃）−、酸素原子、硫黄原子、−ＮＨ−または−ＮＨ（ＣＨ₃）−を表し、
Ｇ^zは、メチル基、エチル基、プロピル基、イソプロピル基、メトキシ基、エトキシ基、プロポキシ基、イソプロポキシ基、２，２，２−トリフルオロエトキシ基、メチルチオ基、エチルチオ基、プロピルチオ基、イソプロピルチオ基、２，２，２−トリフルオロエチルチオ基、Ｎ，Ｎ−ジメチルアミノ基、Ｎ，Ｎ−ジエチルアミノ基、Ｎ，Ｎ−ジプロピルアミノ基、Ｎ−エチル−Ｎ−メチルアミノ基、Ｎ−メチル−Ｎ−プロピルアミノ基、Ｎ−イソプロピル−Ｎ−メチルアミノ基、Ｎ−メチル−Ｎ−（２，２，２−トリフルオロエチル）アミノ基、Ｎ−メチルアミノ基、Ｎ−エチルアミノ基、Ｎ−プロピルアミノ基、Ｎ−イソプロピルアミノ基またはＮ−（２，２，２−トリフルオロエチル）アミノ基を表し、
ｍは０または１を表す。〕
で示される[発明１]記載のピリミジン化合物； Formula (1z)

[Where,
Q ^z represents —CH ₂ —, —CH (CH ₃ ) —, an oxygen atom, a sulfur atom, —NH— or —NH (CH ₃ ) —,
G ^z is methyl group, ethyl group, propyl group, isopropyl group, methoxy group, ethoxy group, propoxy group, isopropoxy group, 2,2,2-trifluoroethoxy group, methylthio group, ethylthio group, propylthio group, isopropyl Thio group, 2,2,2-trifluoroethylthio group, N, N-dimethylamino group, N, N-diethylamino group, N, N-dipropylamino group, N-ethyl-N-methylamino group, N -Methyl-N-propylamino group, N-isopropyl-N-methylamino group, N-methyl-N- (2,2,2-trifluoroethyl) amino group, N-methylamino group, N-ethylamino group N-propylamino group, N-isopropylamino group or N- (2,2,2-trifluoroethyl) amino group,
m represents 0 or 1; ]
A pyrimidine compound as described in [Invention 1];

In the formula (1z), Q ^z is _{-CH 2 -, - CH (CH} 3) - or an oxygen atom [Invention 1] pyrimidine compound according;

In formula (1z), G ^z is an ethyl group, a methoxy group, a methylthio group or an N, N-diethylamino group.

In the formula (1z), Q ^z is —CH ₂ —, —CH (CH ₃ ) — or an oxygen atom, and G ^z is an ethyl group, methoxy group, methylthio group or N, N-diethylamino group [Invention 1 ] The pyrimidine compound of description;

Next, the manufacturing method of this invention compound is demonstrated.

The compound of the present invention can be produced, for example, according to the following (Production Method 1) to (Production Method 9).

〔式中、Ｊ、Ｌ、Ａ、Ｅ、Ｇ、Ｒ^x、ｎおよびｍは前記と同じ意味を表し、Ｘ³は、臭素原子またはヨウ素原子を表し、Ｒ^y1は、群αより選ばれる１個以上の原子もしくは基を有していてもよいＣ１−Ｃ６鎖式炭化水素基またはシクロプロピル基を表し、Ｌｇは、塩素原子、臭素原子、ヨウ素原子、メタンスルホニルオキシ基、パラトルエンスルホニルオキシ基、または、トリフルオロメタンスルホニルオキシ基等の脱離基を表す。〕
・（５ａ）→（３）
化合物（５ａ）と金属マグネシウムとを反応させることによって生成するグリニャール反応剤を、式（２）で示されるアミド化合物と反応させることにより化合物（３）を製造することができる。
該反応は、通常溶媒の存在下行われ、該反応に用いられる溶媒としては、例えばジエチルエーテル、テトラヒドロフラン等のエーテル類が挙げられる。
化合物（５ａ）１モルに対して、金属マグネシウムは通常１モルの割合で用いられるが、適宜変更することができる。また、必要に応じて触媒量の活性化剤を加えて、金属マグネシウムを活性化させることができる。該活性化剤としては、例えば、ヨウ素、１，２−ジブロモエタンが挙げられる。
化合物（５ａ）と金属マグネシウムとの反応における反応温度は、通常室温から用いる溶媒の沸点の範囲であり、反応時間は、通常瞬時から１時間の範囲である。
化合物（５ａ）１モルに対して化合物（２）は通常１モルの割合で用いられるが、適宜変更することができる。
生成したグリニャール反応剤と化合物（２）との反応における反応温度は、通常−７８℃から溶媒の沸点の範囲であり、反応時間は、通常０．１時間から２４時間の範囲である。
反応終了後は、通常の後処理操作を行うことにより、化合物（３）を単離することができる。
・（３）→（７）
化合物（３）を還元することにより、化合物（７）を製造することができる。
還元方法としては、例えば、水素化ホウ素ナトリウムを用いる還元反応が挙げらる。化合物（３）１モルに対して、水素化ホウ素ナトリウムは通常０．２５モル〜１モルの割合で用いられるが、適宜変更することができる。
該反応は、通常溶媒の存在下行われ、該反応に用いられる溶媒としては、例えばメタノール、エタノール、イソプロピルアルコール等のアルコール類が挙げられる。
該反応における反応温度は、通常０℃から溶媒の沸点の範囲である。
該反応における反応時間は、通常瞬時から２４時間の範囲である。
反応終了後は、通常の後処理操作を行うことにより、化合物（７）を単離することができる。
・（５ａ）→（７）
化合物（５ａ）をアルキルリチウム化合物と反応させた後に、生成する反応中間体と式（６）で示されるカルボニル化合物と反応させることにより、化合物（７）を製造することができる。
該反応は、通常溶媒の存在下行われ、該反応に用いられる溶媒としては、例えばジエチルエーテル、テトラヒドロフラン、エチレングリコールジメチルエーテル、１，４−ジオキサンなどのエーテル類、トルエン、キシレン等の芳香族炭化水素類が挙げられる。
該反応に用いられるアルキルリチウム化合物としては、例えば、ブチルリチウムが挙げられる。化合物（５ａ）１モルに対して、アルキルリチウム化合物は通常１モルの割合で用いられるが、適宜変更することができる。
化合物（５ａ）とアルキルリチウム化合物との反応における反応温度は、通常−７８℃から−５０℃の範囲であり、反応時間は、通常瞬時から１時間の範囲である。
化合物（５ａ）１モルに対して化合物（６）は通常１モルの割合で用いられるが、適宜変更することができる。
該反応中間体と化合物（６）との反応における反応温度は、通常−７８℃から３０℃の範囲であり、反応時間は、通常０．１時間から２４時間の範囲である。
反応終了後は、反応混合物に水または塩化アンモニウム水溶液等を注加した後、有機溶媒で抽出し、通常の後処理操作を行うことにより、化合物（７）を単離することができる。
・（４）→（７）
化合物（４）をリチオ化した後に、生成する反応中間体と式（１７）で示されるカルボニル化合物と反応させることにより、化合物（７）を製造することができる。
リチオ化に用いられるリチウム化合物としては、例えば、ブチルリチウム、ｓｅｃ−ブチルリチウム、ｔｅｒｔ−ブチルリチウム等のアルキルリチウム化合物、リチウムジイソプロピルアミド、リチウムテトラメチルピペリジド等のリチウムジアルキルアミド化合物が挙げられる。
中でも、化合物（４）のうち、Ｇが−ＮＨＣ（Ｏ）ｔ−Ｂｕである化合物のリチオ化は、Ｎ，Ｎ，Ｎ’，Ｎ’−テトラメチルエチレンジアミン（以下、ＴＭＥＤＡと記す。）の存在下、ブチルリチウムを用いて行うことができる。
該反応は、通常溶媒の存在下行われ、該反応に用いられる溶媒としては、例えばジエチルエーテル、テトラヒドロフラン、エチレングリコールジメチルエーテル、１，４−ジオキサンなどのエーテル類が挙げられる。
化合物（４）１モルに対して、ブチルリチウムおよびＴＭＥＤＡはそれぞれ通常１モルの割合で用いられるが、適宜変更することができる。
化合物（４）とブチルリチウムとの反応における反応温度は、通常−７８℃から３０℃の範囲であり、反応時間は、通常０．１時間から２４時間の範囲である。
該反応中間体と化合物（１７）との反応における反応温度は、通常−７８℃から３０℃の範囲であり、反応時間は、通常０．１時間から２４時間の範囲である。
反応終了後は、通常の後処理操作を行うことにより、化合物（７）を単離することができる。
・（７）→（１ａ）
本発明化合物（１ａ）は、化合物（７）を脱ヒドロキシ化することにより製造することができる。脱ヒドロキシ化の方法としては、例えば、接触水素還元反応などが挙げられる。
接触水素還元反応は、溶媒および触媒の存在下、水素と反応させて行う。
該反応に用いられる溶媒としては、例えば酢酸が挙げられる。また必要に応じて硫酸等の鉱酸を加えることができ、その場合のモル比は化合物（７）１モルに対して、通常０．０１モル〜１０モルである。
該反応に用いられる触媒としては、例えば、パラジウム炭素等が挙げられる。
該反応における、水素圧は通常１気圧から５気圧である。
該反応における反応時間は、通常０．１時間から２４時間の範囲である。
反応終了後は、ろ過によって触媒を除去した後、通常の後処理操作を行うことにより、本発明化合物（１ａ）を単離することができる。
・（１ａ）→（１ｂ）
さらに、本発明化合物（１ａ）とリチウムジイソプロピルアミド（以下、ＬＤＡと記す。）等の塩基とを反応させた後、Ｒ^y1−Ｌｇで示される化合物と反応させることにより、本発明化合物（１ｂ）を製造することもできる。 (Production method 1)
Among the compounds of the present invention, a compound in which Q is Q1 can be produced, for example, according to the following scheme.

[Wherein, J, L, A, E, G, R ^x , n and m represent the same meaning as described above, X ³ represents a bromine atom or an iodine atom, and R ^y1 represents 1 selected from the group α. Represents a C1-C6 chain hydrocarbon group or cyclopropyl group optionally having one or more atoms or groups, and Lg is a chlorine atom, a bromine atom, an iodine atom, a methanesulfonyloxy group, a paratoluenesulfonyloxy group Or a leaving group such as a trifluoromethanesulfonyloxy group. ]
・ (5a) → (3)
Compound (3) can be produced by reacting a Grignard reactant produced by reacting compound (5a) with metallic magnesium with an amide compound represented by formula (2).
The reaction is usually performed in the presence of a solvent, and examples of the solvent used in the reaction include ethers such as diethyl ether and tetrahydrofuran.
Although metal magnesium is normally used in the ratio of 1 mol with respect to 1 mol of compounds (5a), it can change suitably. Further, if necessary, a catalytic amount of an activator can be added to activate the magnesium metal. Examples of the activator include iodine and 1,2-dibromoethane.
The reaction temperature in the reaction of the compound (5a) with metallic magnesium is usually in the range of the boiling point of the solvent used from room temperature, and the reaction time is usually in the range of 1 hour from the instant.
The compound (2) is usually used at a ratio of 1 mol per 1 mol of the compound (5a), but can be appropriately changed.
The reaction temperature in the reaction between the produced Grignard reagent and compound (2) is usually in the range of −78 ° C. to the boiling point of the solvent, and the reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (3) can be isolated by carrying out ordinary post-treatment operations.
・ (3) → (7)
Compound (7) can be produced by reducing compound (3).
Examples of the reduction method include a reduction reaction using sodium borohydride. Although sodium borohydride is normally used in the ratio of 0.25 mol-1 mol with respect to 1 mol of compounds (3), it can change suitably.
The reaction is usually performed in the presence of a solvent, and examples of the solvent used in the reaction include alcohols such as methanol, ethanol, and isopropyl alcohol.
The reaction temperature in the reaction is usually in the range of 0 ° C. to the boiling point of the solvent.
The reaction time in the reaction is usually in the range of 24 hours from the instant.
After completion of the reaction, the compound (7) can be isolated by performing ordinary post-treatment operations.
・ (5a) → (7)
Compound (7) can be produced by reacting compound (5a) with an alkyllithium compound and then reacting the resulting reaction intermediate with a carbonyl compound represented by formula (6).
The reaction is usually carried out in the presence of a solvent. Examples of the solvent used in the reaction include ethers such as diethyl ether, tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane, and aromatic hydrocarbons such as toluene and xylene. Is mentioned.
Examples of the alkyl lithium compound used in the reaction include butyl lithium. The alkyllithium compound is usually used in a proportion of 1 mol with respect to 1 mol of the compound (5a), but can be appropriately changed.
The reaction temperature in the reaction of the compound (5a) with the alkyl lithium compound is usually in the range of −78 ° C. to −50 ° C., and the reaction time is usually in the range of 1 hour from the instant.
The compound (6) is usually used in a ratio of 1 mol per 1 mol of the compound (5a), but can be appropriately changed.
The reaction temperature in the reaction of the reaction intermediate with compound (6) is usually in the range of −78 ° C. to 30 ° C., and the reaction time is usually in the range of 0.1 hour to 24 hours.
After completion of the reaction, the compound (7) can be isolated by pouring water or an aqueous ammonium chloride solution into the reaction mixture, extracting with an organic solvent, and performing a normal post-treatment operation.
・ (4) → (7)
After lithiation of compound (4), compound (7) can be produced by reacting the resulting reaction intermediate with the carbonyl compound represented by formula (17).
Examples of the lithium compound used for lithiation include alkyl lithium compounds such as butyl lithium, sec-butyl lithium, and tert-butyl lithium, and lithium dialkylamide compounds such as lithium diisopropylamide and lithium tetramethylpiperidide.
Among them, among compounds (4), lithiation of a compound in which G is —NHC (O) t-Bu is the presence of N, N, N ′, N′-tetramethylethylenediamine (hereinafter referred to as TMEDA). Below, butyl lithium can be used.
The reaction is usually performed in the presence of a solvent, and examples of the solvent used in the reaction include ethers such as diethyl ether, tetrahydrofuran, ethylene glycol dimethyl ether, and 1,4-dioxane.
Although butyl lithium and TMEDA are each normally used in a ratio of 1 mol with respect to 1 mol of the compound (4), it can be appropriately changed.
The reaction temperature in the reaction between the compound (4) and butyllithium is usually in the range of −78 ° C. to 30 ° C., and the reaction time is usually in the range of 0.1 to 24 hours.
The reaction temperature in the reaction of the reaction intermediate with compound (17) is usually in the range of −78 ° C. to 30 ° C., and the reaction time is usually in the range of 0.1 hour to 24 hours.
After completion of the reaction, the compound (7) can be isolated by performing ordinary post-treatment operations.
・ (7) → (1a)
The compound (1a) of the present invention can be produced by dehydroxylating the compound (7). Examples of the dehydroxylation method include a catalytic hydrogen reduction reaction.
The catalytic hydrogen reduction reaction is performed by reacting with hydrogen in the presence of a solvent and a catalyst.
Examples of the solvent used in the reaction include acetic acid. Moreover, mineral acids, such as a sulfuric acid, can be added as needed, and the molar ratio in that case is 0.01 mol-10 mol normally with respect to 1 mol of compounds (7).
Examples of the catalyst used in the reaction include palladium on carbon.
The hydrogen pressure in the reaction is usually 1 to 5 atmospheres.
The reaction time in the reaction is usually in the range of 0.1 hour to 24 hours.
After completion of the reaction, the compound (1a) of the present invention can be isolated by removing the catalyst by filtration and then performing a usual post-treatment operation.
・ (1a) → (1b)
Further, after reacting the compound (1a) of the present invention with a base such as lithium diisopropylamide (hereinafter referred to as LDA), the compound (1b) of the present invention is reacted with a compound represented by R ^y1 -Lg. Can also be manufactured.

〔式中、Ｊ、Ｌ、Ａ、Ｅ、Ｇ、ｎおよびｍは前記と同じ意味を表し、Ｘ¹は、ハロゲン原子を表す。〕
本発明化合物（１ｃ）は、式（８）で示されるフェノール化合物と、式（９）で示されるハロピリミジン化合物とを、塩基、および、必要に応じて銅化合物の存在下反応させることにより製造することができる。
（１）銅化合物を用いない場合：
Ｘ¹としては塩素原子またはフッ素原子が好ましい。
該反応は、通常溶媒の存在下行われ、該反応に用いられる溶媒としては、例えばテトラヒドロフラン、エチレングリコールジメチルエーテル、１，４−ジオキサンなどのエーテル類、トルエン、キシレン等の芳香族炭化水素類、アセトニトリル等のニトリル類、Ｎ，Ｎ−ジメチルホルムアミド、Ｎ−メチルピロリジノン等の酸アミド類、ジメチルスルホキシド等のスルホキシド類及びこれらの混合物が挙げられる。
該反応において用いられる塩基としては、水酸化ナトリウム、水酸化カリウム、水素化ナトリウム、炭酸カリウム、炭酸セシウム、カリウムtert−ブトキシド等が挙げる。化合物（８）１モルに対して、塩基は通常１モル〜１０モルの割合で用いられる。
化合物（８）１モルに対して化合物（９）は通常１モルの割合で用いられるが、適宜変更することができる。
該反応における反応温度は、通常２０℃から２００℃あるいは溶媒の沸点の範囲である。
該反応における反応時間は、通常０．１時間から２４時間の範囲である。
反応終了後は、通常の後処理操作を行うことにより、本発明化合物（１ｃ）を単離することができる。
（２）銅化合物を用いる場合：
Ｘ¹としては臭素原子またはヨウ素原子が好ましい。
該反応は、通常溶媒の存在下行われ、該反応に用いられる溶媒としては、例えばテトラヒドロフラン、エチレングリコールジメチルエーテル、１，４−ジオキサンなどのエーテル類、トルエン、キシレン等の芳香族炭化水素類、アセトニトリル等のニトリル類、Ｎ，Ｎ−ジメチルホルムアミド、Ｎ−メチルピロリジノン等の酸アミド類、ジメチルスルホキシド等のスルホキシド類及びこれらの混合物が挙げられる。
該反応において用いられる塩基としては、水酸化ナトリウム、水酸化カリウム、水素化ナトリウム、炭酸カリウム、炭酸セシウム、カリウムtert−ブトキシド等が挙げる。化合物（８）１モルに対して、塩基は通常１モル〜１０モルの割合で用いられる。
銅化合物としては、銅粉末、酸化銅（Ｉ）、塩化銅（Ｉ）、臭化銅（Ｉ）、ヨウ化銅（Ｉ）等が挙げられる。化合物（８）１モルに対して、銅化合物は通常０．０１モル〜１０モルの割合で用いられる。
化合物（８）１モルに対して化合物（９）は通常１モルの割合で用いられるが、適宜変更することができる。
該反応における反応温度は、通常５０℃から２００℃あるいは溶媒の沸点の範囲である。
該反応における反応時間は、通常０．１時間から２４時間の範囲である。
反応終了後は、通常の後処理操作を行うことにより、本発明化合物（１ｃ）を単離することができる。 (Production method 2)
Among the compounds of the present invention, a compound in which Q is Q2 can be produced, for example, according to the following scheme.

[Wherein, J, L, A, E, G, n and m represent the same meaning as described above, and X ¹ represents a halogen atom. ]
The compound (1c) of the present invention is produced by reacting a phenol compound represented by the formula (8) with a halopyrimidine compound represented by the formula (9) in the presence of a base and, if necessary, a copper compound. can do.
(1) When no copper compound is used:
X ¹ is preferably a chlorine atom or a fluorine atom.
The reaction is usually performed in the presence of a solvent. Examples of the solvent used in the reaction include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether, and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, acetonitrile, and the like. Nitriles, acid amides such as N, N-dimethylformamide and N-methylpyrrolidinone, sulfoxides such as dimethyl sulfoxide, and mixtures thereof.
Examples of the base used in the reaction include sodium hydroxide, potassium hydroxide, sodium hydride, potassium carbonate, cesium carbonate, potassium tert-butoxide and the like. The base is usually used in the proportion of 1 mol to 10 mol with respect to 1 mol of the compound (8).
The compound (9) is usually used at a ratio of 1 mol per 1 mol of the compound (8), but can be appropriately changed.
The reaction temperature in the reaction is usually in the range of 20 ° C. to 200 ° C. or the boiling point of the solvent.
The reaction time in the reaction is usually in the range of 0.1 hour to 24 hours.
After completion of the reaction, the compound (1c) of the present invention can be isolated by performing ordinary post-treatment operations.
(2) When using a copper compound:
X ¹ is preferably a bromine atom or an iodine atom.
The reaction is usually performed in the presence of a solvent. Examples of the solvent used in the reaction include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether, and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, acetonitrile, and the like. Nitriles, acid amides such as N, N-dimethylformamide and N-methylpyrrolidinone, sulfoxides such as dimethyl sulfoxide, and mixtures thereof.
Examples of the base used in the reaction include sodium hydroxide, potassium hydroxide, sodium hydride, potassium carbonate, cesium carbonate, potassium tert-butoxide and the like. The base is usually used in the proportion of 1 mol to 10 mol with respect to 1 mol of the compound (8).
Examples of the copper compound include copper powder, copper (I) oxide, copper (I) chloride, copper (I) bromide, and copper (I) iodide. A copper compound is normally used in the ratio of 0.01 mol-10 mol with respect to 1 mol of compound (8).
The compound (9) is usually used at a ratio of 1 mol per 1 mol of the compound (8), but can be appropriately changed.
The reaction temperature in the reaction is usually in the range of 50 to 200 ° C. or the boiling point of the solvent.
The reaction time in the reaction is usually in the range of 0.1 hour to 24 hours.
After completion of the reaction, the compound (1c) of the present invention can be isolated by performing ordinary post-treatment operations.

〔式中、Ｊ、Ｌ、Ａ、Ｅ、Ｇ、Ｘ¹、ｎおよびｍは前記と同じ意味を表し、Ｘ³は、臭素原子またはヨウ素原子を表し、ｙ１は１または２を表す。〕
・（１ｄ）の製造
本発明化合物（１ｄ）は、式（１０）で示されるチオフェノール化合物と、式（９）で示されるハロピリミジン化合物とを、塩基、および、必要に応じて銅化合物の存在下反応させるか、あるいは、式（５ｂ）で示されるハロベンゼン化合物と、式（１１）で示されるメルカプトピリミジン化合物とを、塩基、および、銅化合物の存在下反応させることにより製造することができる。
（１）銅化合物を用いない場合：
Ｘ¹としては塩素原子またはフッ素原子が好ましい。
該反応は、通常溶媒の存在下行われ、該反応に用いられる溶媒としては、例えばテトラヒドロフラン、エチレングリコールジメチルエーテル、１，４−ジオキサンなどのエーテル類、トルエン、キシレン等の芳香族炭化水素類、アセトニトリル等のニトリル類、Ｎ，Ｎ−ジメチルホルムアミド、Ｎ−メチルピロリジノン等の酸アミド類、ジメチルスルホキシド等のスルホキシド類及びこれらの混合物が挙げられる。
該反応において用いられる塩基としては、水酸化ナトリウム、水酸化カリウム、水素化ナトリウム、炭酸カリウム、炭酸セシウム、カリウムtert−ブトキシド等が挙げる。化合物（１０）１モルに対して、塩基は通常１モル〜１０モルの割合で用いられる。
化合物（１０）１モルに対して化合物（９）は通常１モルの割合で用いられるが、適宜変更することができる。
該反応における反応温度は、通常２０℃から２００℃あるいは溶媒の沸点の範囲である。
該反応における反応時間は、通常０．１時間から２４時間の範囲である。
反応終了後は、通常の後処理操作を行うことにより、本発明化合物（１ｄ）を単離することができる。
（２）銅化合物を用いる場合：
Ｘ¹としては臭素原子またはヨウ素原子が好ましい。
該反応は、通常溶媒の存在下行われ、該反応に用いられる溶媒としては、例えばテトラヒドロフラン、エチレングリコールジメチルエーテル、１，４−ジオキサンなどのエーテル類、トルエン、キシレン等の芳香族炭化水素類、アセトニトリル等のニトリル類、Ｎ，Ｎ−ジメチルホルムアミド、Ｎ−メチルピロリジノン等の酸アミド類、ジメチルスルホキシド等のスルホキシド類及びこれらの混合物が挙げられる。
該反応において用いられる塩基としては、水酸化ナトリウム、水酸化カリウム、水素化ナトリウム、炭酸カリウム、炭酸セシウム、カリウムtert−ブトキシド等が挙げられる。化合物（１０）または化合物（１１）１モルに対して、塩基は通常１モル〜１０モルの割合で用いられる。
銅化合物としては、銅粉末、酸化銅（Ｉ）、塩化銅（Ｉ）、臭化銅（Ｉ）、ヨウ化銅（Ｉ）等が挙げられる。化合物（１０）または化合物（１１）１モルに対して、銅化合物は通常０．０１モル〜１０モルの割合で用いられる。
化合物（１０）または化合物（１１）１モルに対して、化合物（９）または化合物（５ｂ）は通常１モル用いられるが、適宜変更することができる。
該反応における反応温度は、通常５０℃から２００℃あるいは溶媒の沸点の範囲である。
該反応における反応時間は、通常０．１時間から２４時間の範囲である。
反応終了後は、通常の後処理操作を行うことにより、本発明化合物（１ｄ）を単離することができる。
・（１ｄ）→（１ｅ）
さらに、本発明化合物（１ｄ）を、過酸化水素、メタクロロ過安息香酸（以下、ｍＣＰＢＡと記す。）、過ヨウ素酸ナトリウム等の酸化剤と反応させることにより、本発明化合物（１ｅ）を製造することもできる。 (Production method 3)
Among the compounds of the present invention, a compound in which Q is Q3 can be produced, for example, according to the following scheme.

[Wherein, J, L, A, E, G, X ¹ , n and m represent the same meaning as described above, X ³ represents a bromine atom or an iodine atom, and y 1 represents 1 or 2. ]
-Production of (1d) The compound (1d) of the present invention comprises a thiophenol compound represented by the formula (10) and a halopyrimidine compound represented by the formula (9), a base, and optionally a copper compound. It can be produced by reacting in the presence or by reacting a halobenzene compound represented by formula (5b) with a mercaptopyrimidine compound represented by formula (11) in the presence of a base and a copper compound. .
(1) When no copper compound is used:
X ¹ is preferably a chlorine atom or a fluorine atom.
The reaction is usually performed in the presence of a solvent. Examples of the solvent used in the reaction include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether, and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, acetonitrile, and the like. Nitriles, acid amides such as N, N-dimethylformamide and N-methylpyrrolidinone, sulfoxides such as dimethyl sulfoxide, and mixtures thereof.
Examples of the base used in the reaction include sodium hydroxide, potassium hydroxide, sodium hydride, potassium carbonate, cesium carbonate, potassium tert-butoxide and the like. The base is usually used in the proportion of 1 mol to 10 mol with respect to 1 mol of the compound (10).
The compound (9) is usually used at a ratio of 1 mol per 1 mol of the compound (10), but can be appropriately changed.
The reaction temperature in the reaction is usually in the range of 20 ° C. to 200 ° C. or the boiling point of the solvent.
The reaction time in the reaction is usually in the range of 0.1 hour to 24 hours.
After completion of the reaction, the compound of the present invention (1d) can be isolated by carrying out ordinary post-treatment operations.
(2) When using a copper compound:
X ¹ is preferably a bromine atom or an iodine atom.
The reaction is usually performed in the presence of a solvent. Examples of the solvent used in the reaction include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether, and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, acetonitrile, and the like. Nitriles, acid amides such as N, N-dimethylformamide and N-methylpyrrolidinone, sulfoxides such as dimethyl sulfoxide, and mixtures thereof.
Examples of the base used in the reaction include sodium hydroxide, potassium hydroxide, sodium hydride, potassium carbonate, cesium carbonate, potassium tert-butoxide and the like. The base is usually used in a proportion of 1 mol to 10 mol with respect to 1 mol of the compound (10) or the compound (11).
Examples of the copper compound include copper powder, copper (I) oxide, copper (I) chloride, copper (I) bromide, and copper (I) iodide. A copper compound is normally used in the ratio of 0.01 mol -10 mol with respect to 1 mol of compound (10) or a compound (11).
Although 1 mol of compound (9) or compound (5b) is usually used with respect to 1 mol of compound (10) or compound (11), it can be appropriately changed.
The reaction temperature in the reaction is usually in the range of 50 to 200 ° C. or the boiling point of the solvent.
The reaction time in the reaction is usually in the range of 0.1 hour to 24 hours.
After completion of the reaction, the compound of the present invention (1d) can be isolated by carrying out ordinary post-treatment operations.
・ (1d) → (1e)
Further, the compound (1e) of the present invention is produced by reacting the compound (1d) of the present invention with an oxidizing agent such as hydrogen peroxide, metachloroperbenzoic acid (hereinafter referred to as mCPBA), sodium periodate or the like. You can also.

〔式中、Ｊ、Ｌ、Ａ、Ｅ、Ｇ、Ｒ^z、Ｘ¹、ｎおよびｍは前記と同じ意味を表し、Ｘ⁴は、臭素原子、ヨウ素原子、またはトリフルオロメタンスルホニルオキシ基を表す。〕
本発明化合物（１ｆ）は、式（１２）で示されるアニリン化合物と、式（９）で示されるハロピリミジン化合物とを、塩基、および、必要に応じてパラジウム触媒の存在下反応させるか、あるいは、式（５ｃ）で示される化合物と、式（１３）で示されるアミノピリミジン化合物とを、塩基、および、パラジウム触媒の存在下反応させることにより製造することができる。
（１）パラジウム触媒を用いない場合：
Ｘ¹としては塩素原子またはフッ素原子が好ましい。
該反応は、通常溶媒の存在下行われ、該反応に用いられる溶媒としては、例えばテトラヒドロフラン、エチレングリコールジメチルエーテル、１，４−ジオキサンなどのエーテル類、トルエン、キシレン等の芳香族炭化水素類、アセトニトリル等のニトリル類、Ｎ，Ｎ−ジメチルホルムアミド、Ｎ−メチルピロリジノン等の酸アミド類、ジメチルスルホキシド等のスルホキシド類及びこれらの混合物が挙げられる。
該反応において用いられる塩基としては、例えば、ピリジン、トリエチルアミン、ジイソプロピルエチルアミン等の有機塩基類、水酸化ナトリウム、水酸化カリウム、炭酸カリウム、炭酸セシウム、炭酸水素ナトリウム等が挙げられる。化合物（１２）１モルに対して、塩基は通常１モル〜１０モルの割合で用いられる。
化合物（１２）１モルに対して化合物（９）は通常１モルの割合で用いられるが、適宜変更することができる。
該反応における反応温度は、通常２０℃から、２００℃または溶媒の沸点の範囲である。
該反応における反応時間は、通常０．１時間から２４時間の範囲である。
反応終了後は、通常の後処理操作を行うことにより、本発明化合物（１ｆ）を単離することができる。
（２）パラジウム触媒を用いる場合：
Ｘ¹としては臭素原子またはヨウ素原子が好ましい。
該反応は、通常溶媒の存在下行われ、該反応に用いられる溶媒としては、例えばテトラヒドロフラン、エチレングリコールジメチルエーテル、１，４−ジオキサンなどのエーテル類、トルエン、キシレン等の芳香族炭化水素類が挙げられる。
該反応において用いられる塩基としては、例えば、ナトリウムtert-ブトキシド、炭酸セシウム等が挙げられる。化合物（１２）または化合物（１３）１モルに対して、塩基は通常１モル〜１０モルの割合で用いられる。
該反応において用いられるパラジウム触媒としては、たとえば、｛１，１’−ビス（ジフェニルホスフィノ）フェロセン｝ジクロロパラジウム、およびトリス（ジベンジリデンアセトン）ジパラジウム（以下、Ｐｄ₂(ｄｂａ)₃と記す。）と４，５−ビス(ジフェニルホスフィノ)−９，９−ジメチルキサンテン（以下、キサントホスと記す。）との組み合わせ、等が挙げられる。化合物（１２）または化合物（１３）１モルに対して、パラジウム触媒は通常０．０１〜０．２モルの割合で用いられる。
化合物（１２）または化合物（１３）１モルに対して化合物（９）または化合物（５ｃ）は通常１モルの割合で用いられるが、適宜変更することができる。
該反応における反応温度は、通常２０℃から１００℃の範囲である。
該反応における反応時間は、通常０．１時間から２４時間の範囲である。
反応終了後は、通常の後処理操作を行うことにより、本発明化合物（１ｆ）を単離することができる。 (Production Method 4)
Among the compounds of the present invention, a compound in which Q is Q4 can be produced, for example, according to the following scheme.

[Wherein, J, L, A, E, G, R ^z , X ¹ , n and m represent the same meaning as described above, and X ⁴ represents a bromine atom, an iodine atom or a trifluoromethanesulfonyloxy group. ]
The compound (1f) of the present invention is obtained by reacting an aniline compound represented by the formula (12) and a halopyrimidine compound represented by the formula (9) in the presence of a base and, if necessary, a palladium catalyst, or The compound represented by the formula (5c) and the aminopyrimidine compound represented by the formula (13) can be produced by reacting in the presence of a base and a palladium catalyst.
(1) When no palladium catalyst is used:
X ¹ is preferably a chlorine atom or a fluorine atom.
The reaction is usually performed in the presence of a solvent. Examples of the solvent used in the reaction include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether, and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, acetonitrile, and the like. Nitriles, acid amides such as N, N-dimethylformamide and N-methylpyrrolidinone, sulfoxides such as dimethyl sulfoxide, and mixtures thereof.
Examples of the base used in the reaction include organic bases such as pyridine, triethylamine and diisopropylethylamine, sodium hydroxide, potassium hydroxide, potassium carbonate, cesium carbonate, sodium hydrogen carbonate and the like. The base is usually used in the proportion of 1 mol to 10 mol with respect to 1 mol of the compound (12).
The compound (9) is usually used at a ratio of 1 mol per 1 mol of the compound (12), but can be appropriately changed.
The reaction temperature in the reaction is usually in the range of 20 ° C. to 200 ° C. or the boiling point of the solvent.
The reaction time in the reaction is usually in the range of 0.1 hour to 24 hours.
After completion of the reaction, the compound of the present invention (1f) can be isolated by carrying out ordinary post-treatment operations.
(2) When using a palladium catalyst:
X ¹ is preferably a bromine atom or an iodine atom.
The reaction is usually performed in the presence of a solvent, and examples of the solvent used in the reaction include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether, and 1,4-dioxane, and aromatic hydrocarbons such as toluene and xylene. .
Examples of the base used in the reaction include sodium tert-butoxide, cesium carbonate and the like. The base is generally used in a proportion of 1 mol to 10 mol with respect to 1 mol of the compound (12) or compound (13).
Examples of the palladium catalyst used in the reaction are {1,1′-bis (diphenylphosphino) ferrocene} dichloropalladium and tris (dibenzylideneacetone) dipalladium (hereinafter referred to as Pd ₂ (dba) ₃ . ) And 4,5-bis (diphenylphosphino) -9,9-dimethylxanthene (hereinafter referred to as xanthophos), and the like. The palladium catalyst is usually used in a proportion of 0.01 to 0.2 mol with respect to 1 mol of the compound (12) or the compound (13).
The compound (9) or the compound (5c) is usually used at a ratio of 1 mol per 1 mol of the compound (12) or the compound (13), but can be appropriately changed.
The reaction temperature in the reaction is usually in the range of 20 ° C to 100 ° C.
The reaction time in the reaction is usually in the range of 0.1 hour to 24 hours.
After completion of the reaction, the compound of the present invention (1f) can be isolated by carrying out ordinary post-treatment operations.

〔式中、Ｊ、Ｌ、Ａ、Ｅ、Ｇ、ｎおよびｍは前記と同じ意味を表し、Ｑ^aは、Ｑ２、Ｑ３またはＱ４を表し、Ｘ¹は、ハロゲン原子を表す。〕
化合物（１５）は、化合物（１４）とジハロピリミジン化合物（１６）とを、塩基の存在下に反応させることにより製造することができる。
化合物（１６）の２つのＸ¹は相異なっていてもよいが、２つのＸ¹がともに塩素原子である化合物が好ましい。
該反応は、前記の製造法２（１）、製造法３（１）または製造法４（１）に準じて行うことができる。
本発明化合物（１ｇ）は、化合物（１５）を脱ハロゲン化することにより製造することができる。脱ハロゲン化の方法としては、例えば、接触水素還元反応などが挙げられる。
接触水素還元反応は、溶媒および触媒の存在下、水素と反応させて行う。
該反応に用いられる溶媒としては、例えば、メタノール、エタノール等のアルコール類、酢酸エチル等のエステル類、酢酸等のカルボン酸類および水が挙げられる。
また必要に応じて塩基または酸を加えることができる。その場合のモル比は化合物（１５）１モルに対して、通常０．０１モル〜１０モルである。
該反応に用いられる塩基としては、例えば、酸化マグネシウム、水酸化ナトリウム、酢酸ナトリウム、トリエチルアミンが挙げられる。酸としては、例えば、硫酸、塩酸が挙げられる。
該反応に用いられる触媒としては、例えば、パラジウム炭素が挙げられる。
該反応における、水素圧は通常１気圧から５気圧である。
該反応における反応時間は、通常０．１時間から２４時間の範囲である。
反応終了後は、ろ過によって触媒を除去した後、通常の後処理操作を行うことにより、本発明化合物（１ｇ）を単離することができる。 (Production method 5)
Among the compounds of the present invention, a compound in which Q is Q2, Q3 or Q4 can be produced, for example, according to the following scheme.

[Wherein, J, L, A, E, G, n and m represent the same meaning as described above, Q ^a represents Q2, Q3 or Q4, and X ¹ represents a halogen atom. ]
Compound (15) can be produced by reacting compound (14) with dihalopyrimidine compound (16) in the presence of a base.
Two X ¹ of the compound (16) may be different from each other, but a compound in which the two X ¹ are both chlorine atoms is preferable.
This reaction can be carried out according to the above Production Method 2 (1), Production Method 3 (1) or Production Method 4 (1).
The compound (1g) of the present invention can be produced by dehalogenating the compound (15). Examples of the dehalogenation method include a catalytic hydrogen reduction reaction.
The catalytic hydrogen reduction reaction is performed by reacting with hydrogen in the presence of a solvent and a catalyst.
Examples of the solvent used in the reaction include alcohols such as methanol and ethanol, esters such as ethyl acetate, carboxylic acids such as acetic acid, and water.
Moreover, a base or an acid can be added as needed. In this case, the molar ratio is usually 0.01 mol to 10 mol with respect to 1 mol of compound (15).
Examples of the base used in the reaction include magnesium oxide, sodium hydroxide, sodium acetate, and triethylamine. Examples of the acid include sulfuric acid and hydrochloric acid.
As a catalyst used for this reaction, palladium carbon is mentioned, for example.
The hydrogen pressure in the reaction is usually 1 to 5 atmospheres.
The reaction time in the reaction is usually in the range of 0.1 hour to 24 hours.
After completion of the reaction, the compound of the present invention (1 g) can be isolated by removing the catalyst by filtration and then performing a usual post-treatment operation.

〔式中、Ｊ、Ｌ、Ａ、Ｅ、Ｑ、Ｒ^b、ｎ、ｍおよびＬｇは前記と同じ意味を表し、Ｒ^b1は、群γより選ばれる１個以上の原子もしくは基を有していてもよいＣ１−Ｃ６鎖式炭化水素基を表し、Ｒ^b2は、ＯＨ基の保護基（例えば、メチル基、メトキシメチル基、ベンジル基等）を表す。〕
・（１ｉ）→（１ｊ’）
本発明化合物（１ｊ’）は、本発明化合物（１ｉ）とＲ^b1ＯＨとを、塩基の存在下に反応させることにより製造することができる。
該反応は、通常溶媒の存在下で行われるが、Ｒ^b1ＯＨを溶媒量用いてもよい。
該反応に用いられる溶媒としては、例えばテトラヒドロフラン、エチレングリコールジメチルエーテル、１，４−ジオキサンなどのエーテル類、トルエン、キシレン等の芳香族炭化水素類、アセトニトリル等のニトリル類、Ｎ，Ｎ−ジメチルホルムアミド、Ｎ−メチルピロリジノン等の酸アミド類、ジメチルスルホキシド等のスルホキシド類及びこれらの混合物が挙げられる。
該反応において用いられる塩基としては、水素化ナトリウム、水酸化ナトリウム、水酸化カリウム、水素化ナトリウム、炭酸カリウム、炭酸セシウム、カリウムtert−ブトキシド等が挙げられる。
本発明化合物（１ｉ）１モルに対して、Ｒ^b1ＯＨが通常１〜１０モルの割合、塩基が通常１〜１０モルの割合で用いられる。
該反応の反応温度は、通常０℃〜溶媒の沸点の範囲であり、反応時間は通常０．１時間から２４時間の範囲である。
反応終了後は、反応終了後は、通常の後処理操作を行うことにより、本発明化合物（１ｊ’）を単離することができる。
・（１ｌ）→（１ｋ）
本発明化合物（１ｋ）は、本発明化合物（１ｌ）を脱保護することにより製造することができる。
保護基であるＲ^b2としては、例えば、メチル基、メトキシメチル基およびベンジル基が挙げられ、当業者に公知の方法で脱保護することができる。
・（１ｋ）→（１ｊ）
本発明化合物（１ｊ）は、本発明化合物（１ｋ）とＲ^bＬｇとを、塩基の存在下に反応させることにより製造することができる。
該反応に用いられる溶媒としては、例えばテトラヒドロフラン、エチレングリコールジメチルエーテル、１，４−ジオキサンなどのエーテル類、トルエン、キシレン等の芳香族炭化水素類、アセトニトリル等のニトリル類、Ｎ，Ｎ−ジメチルホルムアミド、Ｎ−メチルピロリジノン等の酸アミド類、ジメチルスルホキシド等のスルホキシド類及びこれらの混合物が挙げられる。
該反応に用いられる塩基としては、例えば水素化ナトリウム等のアルカリ金属水素化物類、炭酸カリウム、炭酸カリウム、炭酸セシウム、炭酸水素ナトリウム等の炭酸塩類等、水酸化ナトリウム、水酸化カリウム等の金属水酸化物、ピリジン、トリエチルアミン、ジイソプロピルエチルアミン等の有機塩基類、水酸化ナトリウム、水酸化カリウム、炭酸カリウム、炭酸セシウム、炭酸水素ナトリウム等が挙げられる。本発明化合物（１ｋ）１モルに対して、塩基は通常１モル〜１０モルの割合で用いられる。
本発明化合物（１ｋ）１モルに対して、Ｒ^bＬｇは通常１モルの割合で用いられるが、適宜変更することができる。
該反応の反応温度は、通常０℃〜溶媒の沸点の範囲であり、反応時間は通常０．１時間から２４時間である。
反応終了後は、反応終了後は、通常の後処理操作を行うことにより、本発明化合物（１ｊ）を単離することができる。
なお、本発明化合物（１ｊ）は本発明化合物（１ｊ’）を包含する。 (Production method 6)
Among the compounds of the present invention, a compound in which G is G2 can be produced, for example, according to the following scheme.

[Wherein, J, L, A, E, Q, R ^b , n, m and Lg have the same meaning as described above, and R ^b1 has one or more atoms or groups selected from the group γ. Represents an optionally substituted C1-C6 chain hydrocarbon group, and R ^b2 represents an OH-protecting group (for example, a methyl group, a methoxymethyl group, a benzyl group, etc.). ]
・ (1i) → (1j ′)
The compound (1j ′) of the present invention can be produced by reacting the compound (1i) of the present invention with R ^b1 OH in the presence of a base.
The reaction is usually performed in the presence of a solvent, but R ^b1 OH may be used in an amount of a solvent.
Examples of the solvent used in the reaction include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, nitriles such as acetonitrile, N, N-dimethylformamide, Examples thereof include acid amides such as N-methylpyrrolidinone, sulfoxides such as dimethyl sulfoxide, and mixtures thereof.
Examples of the base used in the reaction include sodium hydride, sodium hydroxide, potassium hydroxide, sodium hydride, potassium carbonate, cesium carbonate, potassium tert-butoxide and the like.
Present compound (1i) with respect to 1 mole, the ratio R ^b1 OH is generally 1 to 10 mol and the base is generally used at a ratio of 1 to 10 mol.
The reaction temperature of the reaction is usually in the range of 0 ° C. to the boiling point of the solvent, and the reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound of the present invention (1j ′) can be isolated by carrying out a usual post-treatment operation after the reaction.
・ (1l) → (1k)
The compound (1k) of the present invention can be produced by deprotecting the compound (1l) of the present invention.
Examples of the protective group R ^b2 include a methyl group, a methoxymethyl group, and a benzyl group, which can be deprotected by methods known to those skilled in the art.
・ (1k) → (1j)
The compound (1j) of the present invention can be produced by reacting the compound (1k) of the present invention with R ^b Lg in the presence of a base.
Examples of the solvent used in the reaction include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, nitriles such as acetonitrile, N, N-dimethylformamide, Examples thereof include acid amides such as N-methylpyrrolidinone, sulfoxides such as dimethyl sulfoxide, and mixtures thereof.
Examples of the base used in the reaction include alkali metal hydrides such as sodium hydride, carbonates such as potassium carbonate, potassium carbonate, cesium carbonate and sodium hydrogen carbonate, and metal water such as sodium hydroxide and potassium hydroxide. Examples thereof include oxides, organic bases such as pyridine, triethylamine, diisopropylethylamine, sodium hydroxide, potassium hydroxide, potassium carbonate, cesium carbonate, sodium hydrogen carbonate and the like. The base is usually used in a proportion of 1 mol to 10 mol with respect to 1 mol of the compound (1k) of the present invention.
Present compound (1k) with respect to 1 mole, R ^b Lg is used usually in a proportion of 1 mole, but may be appropriately changed.
The reaction temperature of the reaction is usually in the range of 0 ° C. to the boiling point of the solvent, and the reaction time is usually 0.1 to 24 hours.
After completion of the reaction, the compound of the present invention (1j) can be isolated by carrying out ordinary post-treatment operations after the reaction.
In addition, this invention compound (1j) includes this invention compound (1j ').

〔式中、Ｊ、Ｌ、Ａ、Ｅ、Ｑ、ｎおよびｍは前記と同じ意味を表し、Ｒ^c1は、群γより選ばれる１個以上の原子もしくは基を有していてもよいＣ１−Ｃ６鎖式炭化水素基を表す。〕
本発明化合物（１ｍ）は、本発明化合物（１ｉ）とＲ^c1ＳＨとを、塩基の存在下に反応させることにより製造することができる。
該反応に用いられる溶媒としては、例えばテトラヒドロフラン、エチレングリコールジメチルエーテル、１，４−ジオキサンなどのエーテル類、トルエン、キシレン等の芳香族炭化水素類、アセトニトリル等のニトリル類、Ｎ，Ｎ−ジメチルホルムアミド、Ｎ−メチルピロリジノン等の酸アミド類、ジメチルスルホキシド等のスルホキシド類及びこれらの混合物が挙げられる。
該反応に用いられる塩基としては、例えば水素化ナトリウム、水酸化ナトリウム、水酸化カリウム、炭酸カリウム、炭酸セシウム、カリウムtert−ブトキシド等が挙げられる。
本発明化合物（１ｉ）１モルに対して、Ｒ^c1ＳＨが通常１〜１０モルの割合、塩基が通常１〜１０モルの割合で用いられる。
該反応の反応温度は通常０℃〜溶媒の沸点の範囲であり、反応時間は通常０．１〜２４時間の範囲である。
反応終了後は、通常の後処理操作を行うことにより、本発明化合物（１ｍ）を単離することができる。
この反応終了後、本発明化合物（１ｍ）に対して、更に当業者に公知の酸化反応を行うことにより、本発明化合物（１ｍ）における−ＳＲ^c1を−Ｓ(Ｏ)_z1Ｒ^c1（この場合、ｚ１は１または２を表す）に変換することもできる。 (Production method 7)
Among the compounds of the present invention, a compound in which G is G3 can be produced, for example, according to the following scheme.

[Wherein, J, L, A, E, Q, n and m represent the same meaning as described above, and R ^c1 may have one or more atoms or groups selected from group γ. Represents a C6 chain hydrocarbon group. ]
The compound (1m) of the present invention can be produced by reacting the compound (1i) of the present invention with R ^c1 SH in the presence of a base.
Examples of the solvent used in the reaction include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, nitriles such as acetonitrile, N, N-dimethylformamide, Examples thereof include acid amides such as N-methylpyrrolidinone, sulfoxides such as dimethyl sulfoxide, and mixtures thereof.
Examples of the base used in the reaction include sodium hydride, sodium hydroxide, potassium hydroxide, potassium carbonate, cesium carbonate, potassium tert-butoxide and the like.
R 1 ^C1 SH is usually used in a proportion of 1 to 10 mol, and a base is usually used in a proportion of 1 to 10 mol with respect to 1 mol of the compound (1i) of the present invention.
The reaction temperature of the reaction is usually in the range of 0 ° C. to the boiling point of the solvent, and the reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound of the present invention (1m) can be isolated by carrying out ordinary post-treatment operations.
After completion of this reaction, the present compound (1m) is further subjected to an oxidation reaction known to those skilled in the art to convert -SR ^c1 in the present compound (1m) to -S (O) _z1 R ^c1 (in this case) , Z1 represents 1 or 2).

〔式中、Ｊ、Ｌ、Ａ、Ｅ、Ｑ、Ｒ^d、Ｒ^e、ｎ、ｍおよびＬｇは前記と同じ意味を表す。〕
・（１ｎ）→（１ｏ）
本発明化合物（１ｏ）は、本発明化合物（１ｎ）とＲ^dＬｇとを、塩基の存在下に反応させることにより製造することができる。
該反応に用いられる溶媒としては、例えばテトラヒドロフラン、エチレングリコールジメチルエーテル、１，４−ジオキサンなどのエーテル類、トルエン、キシレン等の芳香族炭化水素類、アセトニトリル等のニトリル類、Ｎ，Ｎ−ジメチルホルムアミド、Ｎ−メチルピロリジノン等の酸アミド類、ジメチルスルホキシド等のスルホキシド類及びこれらの混合物が挙げられる。
該反応に用いられる塩基としては、例えば水素化ナトリウム等のアルカリ金属水素化物類、炭酸カリウム、炭酸カリウム、炭酸セシウム、炭酸水素ナトリウム等の炭酸塩類等、水酸化ナトリウム、水酸化カリウム等の金属水酸化物、ピリジン、トリエチルアミン、ジイソプロピルエチルアミン等の有機塩基類、水酸化ナトリウム、水酸化カリウム、炭酸カリウム、炭酸セシウム、炭酸水素ナトリウム等が挙げられる。本発明化合物（１ｎ）１モルに対して、塩基は通常１モル〜２モルの割合で用いられる。
本発明化合物（１ｎ）１モルに対して、Ｒ^dＬｇが通常１モルの割合で用いられるが適宜変更することができる。
該反応の反応温度は通常０℃〜溶媒の沸点の範囲であり、反応時間は通常０．１時間から２４時間の範囲である。
反応終了後は、通常の後処理操作を行うことにより、本発明化合物（１ｏ）を単離することができる。
・（１ｏ）→（１ｐ）
さらに、本発明化合物（１ｏ）に対して、上記に準じる方法でＲ^eＬｇを反応させることにより、本発明化合物（１ｐ）を製造することができる。
また、Ｒ^dまたはＲ^eが１級または２級アルキル基である場合には、上記の方法に代えて、本発明化合物（１ｎ）または本発明化合物（１ｏ）と、アルデヒドまたはケトン化合物とを還元剤の存在下反応させることにより、本発明化合物（１ｏ）または本発明化合物（１ｐ）を製造することもできる。
該反応に用いられる還元剤としては、例えば、トリアセトキシ水素化ホウ素ナトリウムが挙げられる。本発明化合物（１ｎ）または本発明化合物（１ｏ）１モルに対して、トリアセトキシ水素化ホウ素ナトリウムは１〜５モルの割合で用いられる。
該反応に用いられる溶媒としては、例えばテトラヒドロフラン、エチレングリコールジメチルエーテル、１，４−ジオキサンなどのエーテル類、トルエン、キシレン等の芳香族炭化水素類、ジクロロメタン、クロロホルム等のハロゲン化炭化水素類及びこれらの混合物が挙げられる。また、必要に応じて酢酸等のカルボン酸類を加えて反応を行う。
本発明化合物（１ｎ）または本発明化合物（１ｏ）１モルに対して、アルデヒドまたはケトン化合物は通常１モルの割合で用いられるが適宜変更することができる。
該反応の反応温度は通常０℃〜溶媒の沸点の範囲であり、反応時間は通常０．１時間から２４時間の範囲である。
反応終了後は、通常の後処理操作を行うことにより、本発明化合物（１ｏ）または本発明化合物（１ｐ）を単離することができる。 (Production method 8)
Among the compounds of the present invention, a compound in which G is G4 can be produced, for example, according to the following scheme.

[Wherein, J, L, A, E, Q, R ^d , ^Re , n, m and Lg have the same meaning as described above. ]
・ (1n) → (1o)
The compound (1o) of the present invention can be produced by reacting the compound (1n) of the present invention with R ^d Lg in the presence of a base.
Examples of the solvent used in the reaction include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, nitriles such as acetonitrile, N, N-dimethylformamide, Examples thereof include acid amides such as N-methylpyrrolidinone, sulfoxides such as dimethyl sulfoxide, and mixtures thereof.
Examples of the base used in the reaction include alkali metal hydrides such as sodium hydride, carbonates such as potassium carbonate, potassium carbonate, cesium carbonate and sodium hydrogen carbonate, and metal water such as sodium hydroxide and potassium hydroxide. Examples thereof include oxides, organic bases such as pyridine, triethylamine, diisopropylethylamine, sodium hydroxide, potassium hydroxide, potassium carbonate, cesium carbonate, sodium hydrogen carbonate and the like. The base is usually used in a proportion of 1 mol to 2 mol with respect to 1 mol of the compound (1n) of the present invention.
R ^d Lg is usually used in a proportion of 1 mol per 1 mol of the compound (1n) of the present invention, but can be appropriately changed.
The reaction temperature is usually in the range of 0 ° C. to the boiling point of the solvent, and the reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound of the present invention (1o) can be isolated by carrying out ordinary post-treatment operations.
・ (1o) → (1p)
Furthermore, this invention compound (1p) can be manufactured by making Re ^e Lg react with this invention compound (1o) by the method according to the above.
When R ^d or R ^e is a primary or secondary alkyl group, the present compound (1n) or the present compound (1o) and an aldehyde or ketone compound are reduced instead of the above method. The present compound (1o) or the present compound (1p) can also be produced by reacting in the presence of an agent.
Examples of the reducing agent used in the reaction include sodium triacetoxyborohydride. Sodium triacetoxyborohydride is used in a ratio of 1 to 5 moles with respect to 1 mole of the compound (1n) or the compound (1o) of the present invention.
Examples of the solvent used in the reaction include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether, and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, halogenated hydrocarbons such as dichloromethane and chloroform, and the like. A mixture is mentioned. Moreover, it reacts by adding carboxylic acids, such as an acetic acid, as needed.
The aldehyde or ketone compound is usually used at a ratio of 1 mole per 1 mole of the compound (1n) or the compound (1o) of the present invention, but can be appropriately changed.
The reaction temperature is usually in the range of 0 ° C. to the boiling point of the solvent, and the reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound of the present invention (1o) or the compound of the present invention (1p) can be isolated by carrying out ordinary post-treatment operations.

〔式中、Ｊ、Ｌ、Ａ、Ｅ、Ｇ、Ｑおよびｎは前記と同じ意味を表す。〕
本発明化合物（１ｒ）は、本発明化合物（１ｑ）を酸化剤と反応させることにより製造することができる。
該反応は、通常溶媒の存在下で行われる。
該反応に用いられる溶媒としては、例えばジクロロメタン、クロロホルム等の脂肪族ハロゲン化炭化水素類、酢酸、水及びこれらの混合物が挙げられる。
該反応に用いられる酸化剤としては、例えば３−クロロ過安息香酸等のカルボン酸の過酸化物、過酸化水素水等が挙げられる。
本発明化合物（１ｑ）１モルに対して、酸化剤が通常１〜３モルの割合で用いられる。
該反応の反応温度は、通常−２０〜１００℃の範囲であり、反応時間は通常０．１〜２４時間の範囲である。
反応終了後は、通常の後処理操作を行うことにより、本発明化合物（１ｒ）を単離することができる。 (Production method 9)
Among the compounds of the present invention, a compound in which m is 1 can be produced, for example, according to the following scheme.

[Wherein, J, L, A, E, G, Q and n represent the same meaning as described above. ]
The compound (1r) of the present invention can be produced by reacting the compound (1q) of the present invention with an oxidizing agent.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include aliphatic halogenated hydrocarbons such as dichloromethane and chloroform, acetic acid, water, and mixtures thereof.
Examples of the oxidizing agent used in the reaction include peroxides of carboxylic acids such as 3-chloroperbenzoic acid, hydrogen peroxide water, and the like.
An oxidizing agent is normally used in the ratio of 1-3 mol with respect to 1 mol of this invention compounds (1q).
The reaction temperature of the reaction is usually in the range of -20 to 100 ° C, and the reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound of the present invention (1r) can be isolated by carrying out ordinary post-treatment operations.

  Examples of pests for which the compounds of the present invention are effective include harmful arthropods such as harmful insects and harmful mites, linear animals and molluscs. Specific examples of such pests include the following.

Hemiptera: small brown planthopper (Laodelphax striatellus), brown planthopper (Nilaparvata lugens), planthoppers such as Sejirounka (Sogatella furcifera), green rice leafhopper (Nephotettix cincticeps), Taiwan green rice leafhopper (Nephotettix virescens), tea Roh green leafhopper (Empoasca onukii) such as Leafhoppers, cotton aphids (Aphis gossypii), peach aphids (Myzus persicae), radish aphids (Brevicoryne brassicae), snowy aphids (Aphis spiraecola), tulip beetle aphids rosiphum euphorbiae), potato beetle aphids (Aulacorthum solani), barley aphids (Rhopalosiphum padi), citrus aphids (Toxoptera citricidus), peach beetles, Stink bugs such as stink bugs (Riptortus clavetus), spider helicopter bugs (Leptocorina chinensis), bark beetles (Eysarcoris parvus), winged beetles (Halyomorpha mista) whitefly such as orariorum, tobacco whitefly (Bemisia tabaci), citrus whitefly (Dialeurodes citris), whitefly (Aleurocanthus spiniferus) and other species of whitefly ), Ruby Beetle (Ceroplastes rubens), Icerya purchasi, Fujino scale (Pranococcus kraunhiae), Pseudococcus longispinis, Pseudococcus longispinis Scale insects such as scale insects (Pseudauracapsis pentagona), bed bugs, bed bugs such as bed bugs (Cimex lectularus), and cetaceans.

  Lepidoptera: rice stem borer (Chilo suppressalis), Sankameiga (Tryporyza incertulas), leaf roller (Cnaphalocrocis medinalis), Watanomeiga (Notarcha derogata), Indian meal moth (Plodia interpunctella), the European corn borer (Ostrinia furnacalis), high Madara Roh moth (Hellula undalis), Japanese medusa such as Shibatatsuga (Pediasia teterrellus), Spodoptera litura, Spodoptera exigua, Ayuyoto (Pseudaletia septata), Atoga ras genus such as ra brassicae, Agrotis ipsilon, Tamanaginiwaba (Prusia nigrisigna), Trichopulsia, Heliotis, Helicoberpa, etc. (Leguminivora glycinivolorella), Azusa yamushiga (Matsusumuraeses azukikivora), Apple wolfberry (Adoxophyes orana fasciata), Chanokokumakuhama hamakiki (Adohomocha). Pseudomonas (Archips fuscopuprineus), Codlinga (Cydia pomonella), etc. , Genus Euprocutis, etc., Suga such as Plutella xylostella, cotton moth (Pectinophora gossypiella) potato, Phthorimaea operculella, etc .; Hitriga, Hirosukoga such as iga (Tinea translucens), Koiga (Tineola bisselliella) and the like.

  Thrips pests: Frankliniella occidentalis, Thrips parmi, etc.

  Diptera: Culex (Culex pipiens pallens), Culex (Culex tritaeniorhynchus), Culex such as Culex quinquefasciatus (Culex quinquefasciatus), Aedes aegypti (Aedes aegypti), Aedes albopictus (Aedes albopictus) Aedes genus such as Anopheles sinensis (Anopheles sinensis), etc. Genus Anopheles, chironomid, housefly (Musca domestica), housefly (Muscina stabulans), etc. D (Agromyza oryzae), rice Hime leafminer (Hydrellia griseola), tomato leafminer, (Liriomyza sativae), legume leafminer (Liriomyza trifolii), leafminer such as the pea (Chromatomyia horticola), chloropidae such as Inekimoguribae (Chlorops oryzae), melon fly (Dacus cucurbitae), fruit flies such as Ceratitis capitata, fruit flies such as Drosophila, Drosophila, Megaseria spiracuralis, Clogmial butterflies, etc. Abu such as gadfly (Tabanus trigonus), and stable flies, and the like.

Coleoptera pests: Western Corn Rootworm (Diabrotica virgifera virgifera), corn rootworm such as southern corn rootworm (Diabrotica undecimpunctata howardi), cupreous chafer (Anomala cuprea), rufocuprea (Anomala rufocuprea), chafers such as Japanese beetle (Popillia japonica) , Weevil (Sitophilus zeamais), Rice weevil (Lissohoprus oryzophilus), Azuki beetle (Callosobrchuchus chiensis), Echonocnemus quail weevil such as Onomus grandis and Sphenophorus venatus Phyllotreta striola), Colorado potato beetle (Leptinotarsa decemlineata) and other potato beetles, Anthrenus verbasci, Harajiro beetle worm (Dermestes calculus L) Iderma serricorne, etc., Epilacunas such as Epilachna vigintioctopuntata, Lyctus brunneus, pine beetle longhorn beetles such as malasica), click beetles (Agriotes spp.), and the leaf beetle (Paederus fuscipes).

  Diptera: Tocusama grasshopper (Locusta migratoria), Kera (Gryllotalpa africana), Oxya yezoensis, Scarabae (Oxya japonica), and crickets.

Lepidoptera: Cat fleas (Ctenocephalides felis), Dog fleas (Ctenocephalides canis), Human fleas (Pulex irritans), Xenopsilla cheopes, etc.

Lice insect pests: pediculus humanus corporis, phethyrus pubis, cattle lice (Haematopinus eurysternus), sheep lice (Dalmalinia ovis), pig lice

  Hymenoptera: Monomorium phalaosis, Formica fusca japonica, Ochellelus glove, pistomrme puns, pol. Spr. Such as ants, wasps, scallops, wasp (Athalia rosae), Japanese bee (Athalia japonica), and the like.

  Cockroach pests: German cockroaches (Blatella germanica), Black cockroaches (Periplaneta furiginosa), American cockroaches (Periplaneta americana), Japanese cockroach (Peripraneta brunet)

  Termite pests: Reticulites perstus, Cypterforms minorus, Incitermes minors, Cyptotermes domesticus, Owanstermus Glypoptermes satsumensis), Glypoptermes nakajimai, Gyptotermes fuscus, Glyptotermes kodamai, Kushimoto Roari (Glyptotermes kushimensis), giant termite (Hodotermopsis japonica), Kou Shu Ye termite (Coptotermes guangzhoensis), Amami termites (Reticulitermes miyatakei), R. flavipes (Reticulitermes flaviceps amamianus), Kang Mont termites (Reticulitermes sp.), Takasago termite (Nasutitermes takasagoensis) , Peripritermes nitobei, Sinocapriteres mushae, Reticulitermes flavipes, Re iculitermes hesperus, Reticulitermes virginicus, Reticulitermes tibialis, Heterotermes aureus, Zootermopsis nevadensis or the like.

  Mite order pests: Taninychus urticae, Kantawa spider mite (Tetranychus kanzawai), citrus spider mite (Panonychus citri), mite spider mite (Pananycos ulmi), spider mite pistula mite (Panthonychus urmi), spider mite pistula mite (Panthonychus urmi), spider mite pistula mite (Panthonychus urmi); Tomato rust mites (Aculops lycopersici), Chinese radish mites (Calacarus carinatus), Chinese prickly ticks (Acaphylla theavagrans), Green rust mites (Eriophyes chibaensis), Apple rust ticles li) Fushidani such as, dust mite such as Chanohokoridani (Polyphagotarsonemus latus), southern Hime Himehadani such as spider mites (Brevipalpus phoenicis), Kenagahadani such, longicornis (Haemaphysalis longicornis), Yamatochimadani (Haemaphysalis flava), Taiwan Kaku ticks (Dermacentor taiwanicus ), Yamato tick (Ixodes ovatus), Schulz tick (Ixodes persulcatus), Black legged tick (Ixodes scapularis), Boobius microplus, Rhipice tick (Rhipicph) Ticks such as anguineus), Tyrophagus (Tyrophagus putrescentiae), grain mites such as Tyrophagus (Tyrophagus similis), farinae (Dermatophagoides farinae), house dust mite such as pteronyssinus (Dermatophagoides ptrenyssnus), Hosotsumedani (Cheyletus eruditus), Stag Tsumedani (Cheyletus malaccensis), claw mites such as Cheyletus moorei, house dust mite (Ornithonyssus bacoti), bird mite (Ornithonysus sylvairum), duck (Derman) Spiders such as Yssus gallinae, tsutsugamushi such as Leptotropidum akamushi, and Chiracanthium japonicum, Latrodectus spiders such as Latrodectus spider.

Lip and leg class: Geeu (Thereuonema hilgendorfi), Tobizukadeka (Scorpendra subspinipes) and the like.
Double leg class: Oxidus gracilis, Nedyopus tambanus, etc.
Isopods: Armadillium vulgare, etc.

Gastropoda: Limax marginatus, Limax flavus, etc.

  Nematodes: rice Shin Galle nematode (Aphelenchoides besseyi), strawberry menu nematode (Nothotylenchus acris), sweet potato root-knot nematode (Meloidogyne incognita), northern root-knot nematode (Meloidogyne hapla), Java root-knot nematode (Meloidogyne javanica), soybean cyst nematode (Heterodera glycines), Potato cyst nematodes (Globodera rostochiensis), Southern nematode crest nematodes (Pratylenchus coffeae), Barley nematode nematodes (Pratylenchus neglectus) and the like.

The pest control agent of the present invention contains the compound of the present invention and an inert carrier. The pest control agent of the present invention is usually a mixture of the compound of the present invention and an inert carrier such as a solid carrier, a liquid carrier, a gaseous carrier, etc., and a surfactant or other formulation adjuvant is added as necessary. Thus, they are formulated into emulsions, oils, powders, granules, wettable powders, flowables, microcapsules, aerosols, smoke agents, poison baits, resin preparations and the like.
The pest control agent of the present invention usually contains 0.01 to 95% by weight of the compound of the present invention.

  Examples of solid carriers used for formulation include clays (kaolin clay, diatomaceous earth, bentonite, fusami clay, acidic clay), synthetic hydrous silicon oxide, talc, ceramics, and other inorganic minerals (sericite, quartz, sulfur). , Activated carbon, calcium carbonate, hydrated silica, etc.), fine fertilizers such as chemical fertilizers (ammonium sulfate, phosphorous acid, ammonium nitrate, urea, ammonium chloride, etc.) and granular materials.

  Examples of the liquid carrier include water, alcohols (methanol, ethanol, isopropyl alcohol, butanol, hexanol, benzyl alcohol, ethylene glycol, propylene glycol, phenoxyethanol, etc.), ketones (acetone, methyl ethyl ketone, cyclohexanone, etc.), aromatic hydrocarbons (Toluene, xylene, ethylbenzene, dodecylbenzene, phenylxylylethane, methylnaphthalene, etc.), aliphatic hydrocarbons (hexane, cyclohexane, kerosene, light oil, etc.), esters (ethyl acetate, butyl acetate, isopropyl myristate, Ethyl oleate, diisopropyl adipate, diisobutyl adipate, propylene glycol monomethyl ether acetate, etc.), nitriles (acetonitrile, isobutyro Tolyl), ethers (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-1-butanol, etc. ), Acid amides (N, N-dimethylformamide, N, N-dimethylacetamide, etc.), halogenated hydrocarbons (dichloromethane, trichloroethane, carbon tetrachloride, etc.), sulfoxides (dimethylsulfoxide, etc.), propylene carbonate and vegetable oil (Soybean oil, cottonseed oil, etc.).

  Examples of the gaseous carrier include fluorocarbon, butane gas, LPG (liquefied petroleum gas), dimethyl ether, and carbon dioxide gas.

  Examples of the surfactant include nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, and polyethylene glycol fatty acid ester, and anions such as alkyl sulfonate, alkyl benzene sulfonate, and alkyl sulfate. Surfactant is mentioned.

  Examples of other adjuvants for preparation include fixing agents, dispersants, colorants and stabilizers, such as casein, gelatin, saccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, Synthetic water-soluble polymers (polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylic acids, etc.), PAP (isopropyl acid phosphate), BHT (2,6-di-tert-butyl-4-methylphenol), BHA (2-tert- And a mixture of butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol).

  The pest control method of the present invention is carried out by applying an effective amount of the compound of the present invention directly to pests and / or to habitats of pests (plants, soil, households, animal bodies, etc.). . In the pest control method of the present invention, the compound of the present invention is usually used in the form of the pest control agent of the present invention.

When the pest control agent of the present invention is used for pest control in the agricultural field, the application amount is 1 to 10,000 g in terms of the amount of the compound of the present invention per 10,000 m ² . When the pest control agent of the present invention is formulated into an emulsion, a wettable powder, a flowable agent, etc., it is usually diluted with water so that the active ingredient concentration is 0.01 to 10000 ppm. Agents, powders, etc. are usually applied as they are.

  These preparations and water dilutions of the preparations may be sprayed directly on pests or plants such as crops to be protected from pests, and in order to control pests that inhabit the soil of cultivated land. You may process to soil.

  Moreover, it can also process by the method of wrapping the resin formulation processed into the sheet form or the string form around the crop, stretching over the crop vicinity, and laying on the stock soil.

When the pest control agent of the present invention is used for controlling pests living in a house, the amount applied is the amount of the compound of the present invention per 1 m ² of treatment area when treated on the surface, usually 0.01. The amount of the compound of the present invention per 1 m ³ of the treatment space is usually 0.01 to 500 mg. When the pest control agent of the present invention is formulated into an emulsion, a wettable powder, a flowable agent, etc., it is usually diluted with water so that the active ingredient concentration is 0.1 to 1000 ppm. Apply aerosols, smoke, poisonous bait, etc. as they are.

The pest control agent of the present invention can be used in farmland where the following “crop” is cultivated.
Agricultural crops: corn, rice, wheat, barley, rye, oat, sorghum, cotton, soybean, peanut, buckwheat, sugar beet, rapeseed, sunflower, sugarcane, tobacco, etc.
Vegetables: Solanum vegetables (eggplants, tomatoes, peppers, peppers, potatoes, etc.), Cucurbitaceae vegetables (cucumbers, pumpkins, zucchini, watermelons, melons, etc.), Brassicaceae vegetables (radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage) , Mustard, broccoli, cauliflower, etc.), asteraceae vegetables (burdock, shungiku, artichokes, lettuce, etc.), liliaceae vegetables (leek, onion, garlic, asparagus), celery family vegetables (carrot, parsley, celery, American scallop, etc.) ), Red crustacean vegetables (spinach, chard, etc.), persimmon vegetables (perilla, mint, basil, etc.), strawberry, sweet potato, yam, taro, etc.
Fruit trees: berries (apples, pears, Japanese pears, quince, quince, etc.), nuclear fruits (peaches, plums, nectarines, ume, sweet cherry, apricot, prunes, etc.) ), Nuts (chestnut, walnut, hazel, almond, pistachio, cashew nut, macadamia nut, etc.), berries (blueberry, cranberry, blackberry, raspberry, etc.), grape, oyster, olive, loquat, banana, coffee, Date palm, coconut palm, oil palm etc.
Trees other than fruit trees: tea, mulberry, flowering trees (Satsuki, camellia, hydrangea, sasanqua, shikimi, sakura, yurinoki, crape myrtle, eustoma, etc.), roadside trees (ash, birch, dogwood, eucalyptus, ginkgo, lilac, maple, oak) , Poplar, redwood, fu, sycamore, zelkova, blackfish, Japanese amberjack, moths, pine, pine, spruce, yew, elm, Japanese cypress, etc.), coral jug, dogwood, cedar, cypress, croton, masaki, kanamochi, etc.
Lawn: Shiba (Nasis, Pleurotus, etc.), Bermudagrass (Neurodonidae, etc.), Bentgrass (Oleoptera, Hykonukagusa, Odonoptera, etc.), Bluegrass (Nagahagusa, Oosuzunokatabira, etc.), Fescue (Oonishi nokegusa, Drosophila, etc.) , Grass, etc.), ryegrass (rat, wheat, etc.), anemonefish, and blue whale.
Other: Flowers (Rose, Carnation, Chrysanthemum, Eustoma, Gypsophila, Gerbera, Marigold, Salvia, Petunia, Verbena, Tulip, Aster, Gentian, Lily, Pansy, Cyclamen, Orchid, Lily of the valley, Lavender, Stock, Habutton, Primula, Poinsettia, gladiolus, cattleya, daisy, symbidium, begonia, etc.), biofuel plants (Jatropha, Curcas, safflower, Amanazuna, switchgrass, Miscanthus, Kusanoshi, Danchiku, Kenaf, cassava, willow, algae, etc.), ornamental plants, etc. .

  “Crop” also includes genetically modified crops.

  The pest control agent of the present invention can be mixed or used in combination with other insecticides, acaricides, nematicides, fungicides, plant growth regulators, herbicides and synergists. Examples of active ingredients of such insecticides, acaricides, nematicides, fungicides, plant growth regulators, herbicides and synergists are shown below.

〔式中、
Ｒ¹⁰⁰は塩素原子、臭素原子またはトリフルオロメチル基を表し、
Ｒ²⁰⁰は塩素原子、臭素原子またはメチル基を表し、
Ｒ³⁰⁰は塩素原子、臭素原子またはシアノ基を表す。〕
で示される化合物、
下記式（Ｌ）

〔式中、
Ｒ¹⁰⁰⁰は塩素原子、臭素原子またはヨウ素原子を表す。〕
で示される化合物、メトキサジアゾン（Ｍｅｔｏｘａｄｉａｚｏｎｅ）、スルフラミド（Ｓｕｌｆｌｕｒａｍｉｄ）、亜ヒ酸（Ａｒｓｅｎｉｃ ａｃｉｄ）、ベンクロチアズ（Ｂｅｎｃｌｏｔｈｉａｚ）、石灰窒素（Ｃａｌｃｉｕｍ ｃｙａｎａｍｉｄｅ）、石灰硫黄合剤（Ｃａｌｃｉｕｍ ｐｏｌｙｓｕｌｆｉｄｅ）、メタム・アンモニウム（Ｍｅｔａｍ−ａｍｍｏｎｉｕｍ）、メタム・ナトリウム（Ｍｅｔａｍ−ｓｏｄｉｕｍ）、オレイン酸カリウム（Ｐｏｔａｓｓｉｕｍ ｏｌｅａｔｅ）、硫黄（Ｓｕｌｆｕｒ）、及びトラロピリル（Ｔｒａｌｏｐｙｒｉｌ）。 Active Ingredient of Insecticide (1) Carbamate Compounds Alaniccarb, Aldicarb, Bendiocarb, Benfurcarb, Butocaboxim, Butoxycarbyl, Butoxycarboxyl = NAC), Carbofuran, Carbosulfan, Cloethocarb, Ethiofencarb, Fenobucarb (BPMC), Fenothiocarb (Fenothiocarb, Fenothiocarb) ratiocarb, isoprocarb (Isoprocarb = MIPC), methiocarb (Methiocarb), methomyl (Methomyl), metorcarb (Metocarb), oxamyl (Oxamyl), pirimicarb (Pro), propoxyl (Pro) ), Triazamate, Trimesacarb, XMC, and Xylylcarb.
(2) Organophosphorus compounds Acetate, Azamethiphos, Azinphos-ethyl, Azinphos-methyl, Kazusafos, Chlorethhophos, Chlorethophos , Chlormephos, Chlorpyrifos, Chlorpyrifos-methyl, Coumaphos, Cyanophos = CYAP, Demeton-S-methyl, Demethon-S Jiku Rubos (Dichlorvos = DDVP), Dicrotophos, Dimethoate, Dimethylvinphos, Disulfoton, EPN, Ethion, Etoprofos, Ethoprophos ), Fenamifos, fenitrothion (MEP), fenthion (MPP), phosphatiate, heptenophos (Imicyfos), isofenphos (Is) Ethoxyaminothio-phosphoryl) salicylate, isoxathion (Isoxathion), malathion (Malathion), mecarbam (Mecarbam), mesulfophos (Mesulfophos), methophos (Methidophos), methophos (Methidophos) (Naled: BRP), ometoate (Omethoate), oxydemethon-methyl, parathion, parathion-methyl, phentoate (Phenhoate = PAP) Phorate, Phosalone, Phosmet = PMP, Phosphamidon, Phoxim, Pirimiphos-meth1, Profenfos (Pro), Profenfos (Profenfos) , Pyrachlorfos, pyridafenthion, quinalphos, sulfotep, tebupyrimfos, temephos, terubfos, terbufos, terbufos nphos), thiomethon (Thiomethon), triazophos (Triazophos), trichlorphone (TRICHPHORON = DEP), bamidthione (Vamidothion), aluminum phosphide (Phiothiophene), rothiophos Formothion (Hydrogen phosphide), Oxydeprofos (ESP), Propaphos (Propaphos), Salicion (Salithion), and Sulprofos.
(3) Pyrethroid compounds Acrinathrin, Allethrin, Benfluthrin, Beta-Cyfluthrin, Bifenthrin, Cycloprothrin, Cycloprothrin (Cycloprothrin) , Cypermethrin, Deltamethrin, Esfenvalerate, Etofenprox, Fenpropatrin, Fenvalerate, Fulcitrate F lucytrinate, flufenprox, flumethrin, fluvalinate, halfenprox, imiprothrin, permethrin, praletrin, prethrin. Resmethrin, Sigma-Cypermethrin, Silafluofen, Tefluthrin, Tralomethrin, Transfluthrin, Tetramethrin thrin), phenothrin, cyphenothrin, alpha-Cypermethrin, zeta-Cypermethrin, lambda cihalothrin (lambda-Cyhalothrin) ), Furamethrin, tau-fluvalinate, methfluthrin, profluthrin, dimethylfluthrin, protrifenbute6, protrifenbute6 4- (Methoxyme L) benzyl (EZ)-(1RS, 3RS; 1RS, 3SR) -2,2-dimethyl-3-prop-1-enylcyclopropanecarboxylate, 2,3,5,6-tetrafluoro-4-methylbenzyl (EZ)-(1RS, 3RS; 1RS, 3SR) -2,2-dimethyl-3-prop-1-enylcyclopropanecarboxylate and 2,3,5,6-tetrafluoro-4- (methoxymethyl) Benzyl (1RS, 3RS; 1RS, 3SR) -2,2-dimethyl-3- (2-methyl-1-propenyl) cyclopropanecarboxylate and the like.
(4) Nereistoxin compounds Cartap, Bensulpap, Thiocylam, Thiosultap, Monosultap, and Bisultap.
(5) Neonicotinoid compounds Imidacloprid (Imidac1oprid), Nitenpyram (Nitenpyram), Acetamiprid (Acetamiprid), Thiamethoxam (Thiamethoxam), Thiacloprid (Thiacloprid) and dinotefurin (in)
(6) Benzoylurea compounds Bistrifluron, Chlorfluazuron, Diflubenzuron, Flucycloxuron, Flufenoxuron, Hexafluuron, Hexafluuron Lufenuron, Novaluron, Noviflumuron, Teflubenzuron, Triflumuron, and fluazuuron.
(7) Phenylpyrazole compounds Acetoprole, Ethiprole, Fipronil, Vaniliprole, Pyriprole, and Pyrafluprole.
(8) Bt toxin insecticide Live spores and produced crystal toxins derived from Bacillus thuringiensis, and mixtures thereof.
(9) Hydrazine compounds Chromafenozide, halofenozide, methoxyphenozide, and tebufenozide.
(10) Organochlorine compounds Aldrin, Dieldrin, Dienochlor, Endosulfan, Methoxychlor, Chlordane, and DDT.
(11) Other insecticide active ingredients Machine oil (Machine oil), nicotine sulfate (Nicotine-sulfate), nicotine (Nicotine), abamectin (Abamectin), emamectin benzoate (Emamectin-benzoate), milbemectin (Milbemectin) (Lepidectin), Spinosad, Spinetoram, Indoxacarb, Metaflumizone, Buprofezine, Cyromene, Cyromene, Cyromene, Cyromene ), Pyriproxyfen, Phenoxycarb, Chlorphenapyr, DNOC, Diafenthiuron, Pymetrozine, Pymetrozine, Pymetrozine Tolfenpyrad, Flurimfen, Flufenerim, Spirotetramat, Spiromesifen, Sulfoxaflor, Chloranthrolitrol orantraniliprole, cyantraniliprole, fulvendiamide,
Following formula (K)

[Where,
R ¹⁰⁰ represents a chlorine atom, a bromine atom or a trifluoromethyl group,
R ²⁰⁰ represents a chlorine atom, a bromine atom or a methyl group,
R ³⁰⁰ represents a chlorine atom, a bromine atom or a cyano group. ]
A compound represented by
The following formula (L)

[Where,
R ¹⁰⁰⁰ represents a chlorine atom, a bromine atom or an iodine atom. ]
, Methoxadiazone, sulfuramide, arsenous acid, benclothiaz, lime nitrogen (Calcium flude) ammonium, Metam-sodium, Potassium oleate, Sulfur, and Tralopyril.

Active ingredients of acaricides: Acequinocyl, Amitraz, Benzoximate, Bifenaate, Bromopropyl, BSPC, Chromethionate, Chromethionate ), Clofentezine, cyflumetofen, dicofol, etoxazole, fenazaquin, fenbutatin oxide, phenothicarb, fenothiocarb. Pyroximate, Fluacrylpyrim, Hexythiaxox, propargite (di), di (R), pyridene (P), piridaben (Pyriben) Diclofen, Spirodiclofen, Amidoflumet, and Cyenopyrafen.

Active ingredient of nematicide Methyl bromide, DD (1,3-Dichloropropene), DCIP, Fostiazate, levamisole hydrochloride, Levisosol, Methylisothiocyanate tartarate), and Imicyafos.

Active ingredients of fungicides: Azaconazole, Vitertanol, Bromuconazole, Cyproconazole, Difenaconol, Dinicoconol, Inicoconol (Fenarimol) Fenbuconazole, Flucilazole, Fluquinconazole, Flutriafol, Hexaconazole, Imazaril (Imazalil) mibenconazole), ipconazole (Ipconazole), metconazole (Metconazole), microbutanyl (Myclobutanil), Nuarimol, oxpoconazole (Oppoconazole), penfazoate (o) Propiconazole, Prothioconazole, Pyrifenox, Simeconazole, Tebuconazole, Tetraconazole, Triazimone fon), triadimenol (Triadimenol), triflumizole (Triflumizole), trifolin (Trifolin), triticonazole (Triticonazole), aldimorph (Dodemorph), fenpropimorph (Forproimorph) , Fenpropidin, Piperalin, Spiroxamine, Fenhexamide, Pyributicarb, Naphtifine, Nabinifine, Terbinafine (Terbinasterol)
Benomyl, Carbendazim, Fuberidazole, Thiabendazole, Thiophaneate, Thiophaneate, Thiophaneate, Thiophanate, Thyphenate ) And other cell division inhibiting bactericidal compounds;
Clozolinate (Chlozolinate), Iprodione (Iprodione), Procymidone (Procymidone), Vinclozoline (Quinoxyfen), Proquinazin (Proquinodil), Fenpiclonil (Fenpiclonil)
Amino acid biosynthesis inhibiting fungicidal compounds such as cyprodinil, pyrimethanil, mepanipyrim;
Bactericidal compounds that inhibit nucleic acid biosynthesis, such as metalaxyl, benalaxyl, oxolinic acid;
Isoprothiolane (Isoprothiolane), Iprobenfos (Iprobenfos), Toluclofos-methyl (Prothiocarb), Dimethomorphic (Benthiatropiprob) Bactericidal compounds that inhibit lipid and membrane synthesis;
Melanin biosynthesis inhibiting bactericidal compounds such as diclocymet, carpropamide, phenoxanil, fthalide, tricyclazole, pyroquilon, etc .;
Azoxystrobin, dimoxystrobin, enestrobin, fluoxastrobin, cresoxime-methyl, methinostrobin (methominostrobin) Strobilurin bactericidal compounds such as Pyroxystrobin, Pyraclostrobin, Pyribencarb Trifloxystrobin;
Carboxin, Oxycarboxin, Mepronil, Flutolanil, Furametopyr, Thifluzamide, Flupy, penthirid, P Anilide fungicidal compounds such as Bixafen, Isopyrazam, Penflufen, Sedaxan, Fluxapyroxad;
A resistance-inducing compound such as acibenzolar-S-methyl, probenazole, thiadinil, isothianil;
Glucan synthesis-inhibiting fungicidal compounds such as validamycin A and polyoxin B;
Protein biosynthesis inhibiting bactericidal compounds such as Blastcidin-S, Kasugamycin, Streptomycin, etc .;
Thiuram, Mancozeb, Chlorothalonil, Captan, Diclofluanid, Folpet, Iminoctaine, Bacteria of Ziram (Zira) Compound;
Amisulbrom; Cyazofamid; Ferimzone; Fluazinam; Binapacryl; Dinocapone; Famoxadone; Famoxadone; Cyflufenamide and the like.

Active ingredient of herbicide (1) Phenoxy fatty acid herbicidal compound 2,4-PA, MCP, MCPB, phenthiol (Phenothio1), mecoprop, Fluroxypyr, Triclopyr, Clomeprop, and Clomeprop Naproanilide.
(2) Benzoic acid herbicidal compound 2,3,6-TBA, dicamba, clopyralid, picloram, aminopyralid, quinclorac, and quinmerac.
(3) Urea herbicidal compounds diuron (Diuron), linuron (Linuron), chlortoluron (Chlortururon), isoproturon (Isoproturon), fluometuron (Isouron) (Isouron), tebuthiuron (Tebuthuron (Tebuthuron) , Cumyluron, Daimuron, and Methyl-daimuron.
(4) Triazine herbicidal compounds Atrazine, Amethrin, Cyanazine, Simazine, Propazine, Simetrin, Dimethametrin, Dimetamethrin ), Triaziflam, and indaziflam.
(5) Bipyridinium herbicidal compound paraquat (Paraquat) and diquat (Diquat).
(6) Hydroxybenzonitrile herbicidal compounds bromoxynil and Ioxynil.
(7) Dinitroaniline herbicidal compound pendimethalin, prodiamine, and trifluralin.
(8) Organophosphorus herbicidal compounds Amiprofos-methyl, Butamifos, Bensulide, Piperophos, Anilofos, Glyphosate, Glufonate, Glufonate, Glufonate P (Glufosinate-P), and Bialaphos.
(9) Carbamate herbicidal compounds di-allate, tri-allate, EPTC, butyrate, benthocarb, esprocarb, molinate, dimepiperate, dimepiperate (Swep), Chlorprofham, Phenmedifam, Phenisopham, Pyributicalb, and Asuram.
(10) Acid amide herbicidal compounds propanil, propyzamide, bromobutide, and etobanzanide.
(11) Chloroacetanilide herbicidal compounds acetochlor (Acetochlor), alachlor (Alaclor), butachlor (Butachlor), dimethenamide (Dimethenamide), propachlor (Metaphachlor), metolachlor (et) Pretilachor), tenylchlor (Theny1ch1or), and petoxamide (Pethoxamide).
(12) Diphenyl ether herbicidal compound acifluorfen (Acifluorfen-sodium), bifenox (Bifenox), oxyfluorfen (Oxyfluorfen), lactofen (Lactofen), fomesafen (ChlophenoxyAclofeni), clomethoxenyl (ChlophenoxyAclofeny).
(13) Cyclic imide herbicidal compounds oxadiazone, cinidone-ethyl, carfentrazone-ethyl, sulfentrazone, full microlac-pentyl, flumilacrac-pentyl Oxazine (Flumioxazin), Pyraflufen-ethyl, Oxadiargyl (Oxadiargyl), Pentoxazone, Fluthiacet-methyl, Butafenzil (Butafenzil) zone), and saflufenacil (Saflufenacil).
(14) Pyrazole herbicidal compounds benzofenap, Pyrazolate, Pyrazoxifene, topramzone, and pyrasulfotole.
(15) Triketone herbicidal compounds isoxaflutole, benzobicyclon, sulcotrione, mesotrione, tembotrione, and tefril trione.
(16) Aryloxyphenoxypropionic acid herbicidal compound Clodinafop-propargyl, Cyhalofop-butyl, Diclohop-methyl, Fenoxaprop-ethyl Fluazifop-butyl, haloxyhop-methyl, quizalofop-ethyl, and metamihop.
(17) Trionoxime herbicidal compounds Alloxydim-sodium, Setoxydim, Butroxidim, Crethodim, Cloproxidim, Cycloxydim, Cycloxydim (Tralkoxydim), and Profoxydim.
(18) sulfonylurea herbicidal compounds chlorsulfuron (Sulfomethuron-methyl), metsulfuron-methyl, chlorimuron-ethyl, trivenuron methyl (18) Tribenuron-methyl), trisulfuron (Triasulfuron), bensulfuron-methyl (Bensulfuron-methyl), thifensulfuron-methyl (pyrizosulfuron-methyl), pyrulsulfuron-methyl- (1) Nicosulfuron (Nico ulfuron, amidosulfuron, minosulfuron, imazosulfuron, rimsulfuron, halosulfuron methyl, sulfulon methyl, sulfulon methyl , Triflusulfuron-methyl, frazasulfuron, cyclosulfamuron, flupirsulfuron, sulfosulfuron, azulizurium Azimsulfuron, ethoxysulfuron, oxasulfuron, iodosulfuron-methyl sodium (Idosulfuron-methyl-sodium), foramsulfuron, mesosulfuron methyl Trisulfursulfuron, Tritosulfuron, Orthosulfururon, Flucetosulfuron, and Propyrisulfuron.
(19) Imidazolinone herbicidal compounds: imazametabenz-methyl, imazametapyr, imazamox, imazapi, imazakin, and imazakin.
(20) Sulfonamide Herbicidal Compounds Flumetslam, Metoslam, Dicloslam, Floraslam, Chloransrammethyl, Penoxsulox, Penoxsulox and Penoxsulox.
(21) Pyrimidinyloxybenzoic acid herbicidal compound Pyrithiobac-sodium, Bispyribac-sodium, Pyriminobac-methyl1, Pyribenzoximid, Pyriphthaloxid And Pyrimisulfan.
(22) Other herbicidal compounds: Bentazone, Bromazone, Terbacil, Chlorthiamid, Isoxaben, Dinoseb, Amitrol, Intrimethyline, Synthylin, C Tridiphane, Dalapon (Dalapon), Diflufenzopyr sodium (Diflufenzopyr-sodium), Dithiopyr (Dithiopyr), Thiazopyr (Thiazopyr), Sodium Flucarbazone (Prolucazone) Nasset (Mefenacet), Flufenacet (Flufenacet), Fentrazamide, Cavenstrole, Indanophan (Indanofan), Oxaziclomephone (R), Bendasate (Benfuresate), N (Norflurazon), Flurtamone (Diflufenican), Diflufenican, Picolinafene (Picolinafene), Beflubutamide (Clonzone), Achromazone (Amicarzone) , Pinoxaden (Pinoxaden), pyraclonil (Pyraclonil), pyroxasulfone (Pyroxasulfone), thien-carbazone methyl (Thiencarbazone-methyl), amino cyclo Pila crawl (Aminocyclopyrachlor), type phen carbazone (Ipfencarbazone), and Mechiozorin (Methiozolin).

Active ingredient of synergist piperonyl butoxide, sesamex, sulfoxide, N- (2-ethylhexyl) -8,9,10-trinorborn-5-ene-2,3-di Carboximide (MGK 264), N-decrimimidazole (N-Decimidizole), WARF-anti-resitant, TBPT, TPP, IBP, PSCP, methyl iodide (CH ₃ I), t-phenyl butyl Tenon (t-Phenylbutenone), Diethylmaleate, DMC, FDMC, ETP, and ETN.

Among the active ingredients that can be used in combination or in combination, as a particularly preferred example, an active ingredient of an insecticide such as cartap hydrochloride, fipronil, methoxyphenozide, tebufenozide, clothianidin, spinosad, spinetoram, chlorantraniliprole or cyantraniliprole, Examples include active ingredients of bactericides such as diclocimet, fusaride, tricyclazole, pyroxylone, azoxystrobin, metminostrobin, orisatrobin, flutolanil, furametopyr, tifluzamide, probenazole, thiazinyl, isothianyl, validamycin, kasugamycin or ferrimzone.

  Hereinafter, the present invention will be described in more detail with reference to production examples, formulation examples, test examples, and the like, but the present invention is not limited to these examples.

  First, the manufacture example of this invention compound is shown below.

Production Example 1
A mixture of 0.25 g of 4-chloropyrimidine, 0.30 g of 4-tert-butylphenol, 0.70 g of cesium carbonate and 3 ml of N-methylpyrrolidinone was stirred at 80 ° C. for 2 hours. Water was poured into the reaction mixture which had been allowed to cool, saturated aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.49 g of 4- (4-tert-butylphenoxy) pyrimidine.
4- (4-tert-Butylphenoxy) pyrimidine (Compound 2-1)

Production Example 2
A mixture of 0.49 g of 4,6-dichloro-5-methylpyrimidine, 0.45 g of 4-tert-butylphenol, 1.08 g of cesium carbonate and 4 ml of N-methylpyrrolidinone was stirred at 70 ° C. for 2 hours and at 100 ° C. for 2 hours. did. Water was poured into the reaction mixture which had been allowed to cool, saturated aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.62 g of 4- (4-tert-butylphenoxy) -6-chloro-5-methylpyrimidine.
¹ H-NMR (CDCl ₃ ) δ: 1.35 (9H, s), 2.42 (3H, s), 7.06 (2H, d), 7.45 (2H, d), 8.39 ( 1H, s).
4- (4-tert-Butylphenoxy) -6-chloro-5-methylpyrimidine (0.50 g), sulfuric acid (0.2 g), ethanol (50 ml) and Pd carbon (catalytic amount) were mixed, and the mixture was heated at room temperature under a hydrogen atmosphere of about 1 atm. For 2 hours. The reaction mixture was filtered and the filtrate was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.07 g of 4- (4-tert-butylphenoxy) -5-methylpyrimidine.
4- (4-tert-butylphenoxy) -5-methylpyrimidine (Compound 2-9)

Production Example 3
A mixture of 0.25 g of 4-chloropyrimidine, 0.33 g of 4-tert-butylthiophenol, 0.70 g of cesium carbonate and 3 ml of N-methylpyrrolidinone was stirred at 80 ° C. for 2 hours. Water was poured into the reaction mixture which had been allowed to cool, saturated aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.59 g of 4- (4-tert-butylphenylthio) pyrimidine.
4- (4-tert-butylphenylthio) pyrimidine (Compound 3-1)

Production Example 4
A mixture of 0.03 g of 4- (4-tert-butylphenylthio) pyrimidine and 2 ml of chloroform was ice-cooled, 0.49 g of metachloroperbenzoic acid (75%) was added, and the mixture was stirred at room temperature for 1 day. A saturated aqueous sodium hydrogen carbonate solution was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.17 g of 4- (4-tert-butylbenzenesulfonyl) pyrimidine.
4- (4-tert-butylbenzenesulfonyl) pyrimidine (Compound 3-3)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：１．３４（９Ｈ，ｓ），３．８６（３Ｈ，ｓ），３．９４（２Ｈ，ｂｒｓ），６．４０（１Ｈ，ｂｒｓ），７．４１−７．５１（４Ｈ，ｍ），８．２１（１Ｈ，ｓ）．
４−（４−ｔｅｒｔ−ブチルフェニルチオ）−６−ヒドラジノ−５−メトキシピリミジン２．０ｇおよびピリジン１０ｍｌの混合物を氷冷し、塩化トシル１．２５ｇを加えて室温で２時間攪拌した。反応混合物を室温まで放冷し、水を加え、酢酸エチルで抽出した。有機層を水洗した後、無水硫酸ナトリウムで乾燥し、減圧下に濃縮した。得られた残渣をシリカゲルクロマトグラフィーに付し、Ｎ−〔６−（４−ｔｅｒｔ−ブチルフェニルチオ）−５−メトキシピリミジン−４−イル〕−Ｎ’−トシルヒドラジン１．３８ｇを得た。
Ｎ−〔６−（４−ｔｅｒｔ−ブチルフェニルチオ）−５−メトキシピリミジン−４−イル〕−Ｎ’−トシルヒドラジン

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：１．３３（９Ｈ，ｓ），２．３５（３Ｈ，ｓ），３．８４（３Ｈ，ｓ），６．９６−７．０２（１Ｈ，ｍ），７．１８（２Ｈ，ｄ），７．３８−７．４８（５Ｈ，ｍ），７．７８（２Ｈ，ｄ），７．８３（１Ｈ，ｓ）．
エチレングリコール３５ｍｌ、水１５ｍｌおよび水酸化ナトリウム０．３ｇの混合物を１００℃に加熱し、そこへＮ−〔６−（４−ｔｅｒｔ−ブチルフェニルチオ）−５−メトキシピリミジン−４−イル〕−Ｎ’−トシルヒドラジン１．２８ｇ、エチレングリコール７ｍｌおよび水３ｍｌの混合物を加え、１００℃で１時間攪拌した。反応混合物を室温まで放冷し、水を加え、酢酸エチルで抽出した。有機層を水洗した後、無水硫酸ナトリウムで乾燥し、減圧下に濃縮した。得られた残渣をシリカゲルクロマトグラフィーに付し、４−（４−ｔｅｒｔ−ブチルフェニルチオ）−５−メトキシピリミジン０．２９ｇを得た。
４−（４−ｔｅｒｔ−ブチルフェニルチオ）−５−メトキシピリミジン（化合物３−１９）

Production Example 5
A mixture of 0.90 g of 4,6-dichloro-5-methoxypyrimidine, 0.83 g of 4-tert-butylthiophenol, 1.77 g of cesium carbonate and 5 ml of N-methylpyrrolidinone was stirred at 80 ° C. for 2 hours. The reaction mixture was allowed to cool to room temperature, water and saturated aqueous ammonium chloride solution were added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 1.33 g of 4- (4-tert-butylphenylthio) -6-chloro-5-methoxypyrimidine.
¹ H-NMR (CDCl ₃ ) δ: 1.36 (9H, s), 4.02 (3H, s), 7.48 (4H, s), 8.37 (1H, s).
A mixture of 1.14 g of 4- (4-tert-butylphenylthio) -6-chloro-5-methoxypyrimidine, 1.0 g of hydrazine monohydrate and 10 ml of triethylamine was stirred with heating under reflux for 4 hours. The reaction mixture was allowed to cool to room temperature, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous sodium sulfate. Concentration under reduced pressure gave 2.34 g of crude 4- (4-tert-butylphenylthio) -6-hydrazino-5-methoxypyrimidine.
4- (4-tert-butylphenylthio) -6-hydrazino-5-methoxypyrimidine

¹ H-NMR (CDCl ₃ ) δ: 1.34 (9H, s), 3.86 (3H, s), 3.94 (2H, brs), 6.40 (1H, brs), 7.41- 7.51 (4H, m), 8.21 (1H, s).
A mixture of 2.0 g of 4- (4-tert-butylphenylthio) -6-hydrazino-5-methoxypyrimidine and 10 ml of pyridine was ice-cooled, 1.25 g of tosyl chloride was added, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was allowed to cool to room temperature, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 1.38 g of N- [6- (4-tert-butylphenylthio) -5-methoxypyrimidin-4-yl] -N′-tosylhydrazine.
N- [6- (4-tert-Butylphenylthio) -5-methoxypyrimidin-4-yl] -N'-tosylhydrazine

¹ H-NMR (CDCl ₃ ) δ: 1.33 (9H, s), 2.35 (3H, s), 3.84 (3H, s), 6.96-7.02 (1H, m), 7.18 (2H, d), 7.38-7.48 (5H, m), 7.78 (2H, d), 7.83 (1H, s).
A mixture of 35 ml of ethylene glycol, 15 ml of water and 0.3 g of sodium hydroxide was heated to 100 ° C., where N- [6- (4-tert-butylphenylthio) -5-methoxypyrimidin-4-yl] -N was added. A mixture of 1.28 g of '-tosylhydrazine, 7 ml of ethylene glycol and 3 ml of water was added, and the mixture was stirred at 100 ° C for 1 hour. The reaction mixture was allowed to cool to room temperature, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.29 g of 4- (4-tert-butylphenylthio) -5-methoxypyrimidine.
4- (4-tert-butylphenylthio) -5-methoxypyrimidine (Compound 3-19)

Production Example 6
A mixture of 0.25 g of 4-chloropyrimidine, 0.30 g of 4-tert-butylaniline, 0.70 g of cesium carbonate and 3 ml of N-methylpyrrolidinone was stirred at 80 ° C. for 2 hours. Water was poured into the reaction mixture which had been allowed to cool, saturated aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.15 g of N- (4-tert-butylphenyl) pyrimidin-4-ylamine.
N- (4-tert-butylphenyl) pyrimidin-4-ylamine (Compound 4-1)

¹H-NMR (CDCl₃) δ: 1.36 (9H, s), 7.54 (2H, dd), 7.90 (1H, dd), 8.04 (2H, dd), 9.02 (1H, d), 9.39 (1H, d).
４−（４−ｔｅｒｔ−ブチルベンゾイル）ピリミジン４９１ｍｇ、水素化ホウ素ナトリウム１５５ｍｇおよびメタノール８ｍｌの混合物を室温で３０分間攪拌した。反応混合物に飽和塩化アンモニウム水溶液を注加した後、酢酸エチルで抽出した。有機層を水洗した後、無水硫酸マグネシウムで乾燥し、減圧下に濃縮した。得られた残渣をシリカゲルクロマトグラフィーに付し、（４−ｔｅｒｔ−ブチルフェニル）−ピリミジン−４−イル−メタノール３９７ｍｇを得た。
（４−ｔｅｒｔ−ブチルフェニル）−ピリミジン−４−イル−メタノール

¹H-NMR (CDCl₃) δ: 1.30 (9H, s), 4.43 (1H, d), 5.72 (1H, d), 7.27-7.31 (3H, m), 7.38 (2H, dd), 8.65 (1H, d), 9.19 (1H, d).
（４−ｔｅｒｔ−ブチルフェニル）−ピリミジン−４−イル−メタノール１４８ｍｇ、トリエチルアミン０．１０ｍｌおよびテトラヒドロフラン３ｍｌの混合物に、氷冷下、塩化アセチル４３μｌを加えた後、室温で５時間攪拌した。反応混合物に飽和炭酸水素ナトリウム水溶液を注加し、酢酸エチルで抽出した。有機層を水洗し、無水硫酸マグネシウムで乾燥した後、減圧下に濃縮し、酢酸＝（４−ｔｅｒｔ−ブチルフェニル）−ピリミジン−４−イル−メチル１７１ｍｇを得た。
酢酸＝（４−ｔｅｒｔ−ブチルフェニル）−ピリミジン−４−イル−メチル

¹H-NMR (CDCl₃) δ: 1.29 (9H, s), 2.22 (3H, s), 6.74 (1H, s), 7.34 (2H, dd), 7.38 (2H, dd), 7.43 (1H, dd), 8.72 (1H, d), 9.17 (1H, d).
酢酸＝（４−ｔｅｒｔ−ブチルフェニル）−ピリミジン−４−イル−メチル１６８ｍｇ、トリエチルアミン０．１３ｍｌ、メタノール１０ｍｌおよびＰｄ炭素（触媒量）を混合し、約１気圧の水素雰囲気下、室温で９時間攪拌した。反応混合物を濾過した後、減圧下に濃縮した。得られた残渣をシリカゲルクロマトグラフィーに付し、４−（４−ｔｅｒｔ−ブチルベンジル）ピリミジン７７ｍｇを得た。
４−（４−ｔｅｒｔ−ブチルベンジル）ピリミジン（化合物１−１）

Production Example 7
To a mixture of 495 mg of N-methoxy-N-methyl-4-pyrimidinecarboxamide and 8 ml of tetrahydrofuran, a solution of 4-tert-butylphenylmagnesium bromide (2.5 g of 4-tert-butylphenylbromide, 0.31 g of magnesium and 10 ml of tetrahydrofuran). 5 ml (prepared) was added dropwise under ice cooling. After stirring at room temperature for 1 hour, 1N hydrochloric acid and saturated aqueous sodium hydrogen carbonate solution were sequentially added to the reaction mixture, and the mixture was filtered. The obtained filtrate was extracted with ethyl acetate, and then the organic layer was washed with water and dried over anhydrous magnesium sulfate. After concentration under reduced pressure, the residue was subjected to silica gel chromatography to obtain 491 mg of 4- (4-tert-butylbenzoyl) pyrimidine.
4- (4-tert-butylbenzoyl) pyrimidine

¹ H-NMR (CDCl ₃ ) δ: 1.36 (9H, s), 7.54 (2H, dd), 7.90 (1H, dd), 8.04 (2H, dd), 9.02 (1H, d), 9.39 (1H, d ).
A mixture of 491 mg of 4- (4-tert-butylbenzoyl) pyrimidine, 155 mg of sodium borohydride and 8 ml of methanol was stirred at room temperature for 30 minutes. A saturated aqueous ammonium chloride solution was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 397 mg of (4-tert-butylphenyl) -pyrimidin-4-yl-methanol.
(4-tert-Butylphenyl) -pyrimidin-4-yl-methanol

¹ H-NMR (CDCl ₃ ) δ: 1.30 (9H, s), 4.43 (1H, d), 5.72 (1H, d), 7.27-7.31 (3H, m), 7.38 (2H, dd), 8.65 (1H , d), 9.19 (1H, d).
To a mixture of 148 mg of (4-tert-butylphenyl) -pyrimidin-4-yl-methanol, 0.10 ml of triethylamine and 3 ml of tetrahydrofuran was added 43 μl of acetyl chloride under ice cooling, and the mixture was stirred at room temperature for 5 hours. Saturated aqueous sodium hydrogen carbonate solution was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 171 mg of acetic acid = (4-tert-butylphenyl) -pyrimidin-4-yl-methyl.
Acetic acid = (4-tert-butylphenyl) -pyrimidin-4-yl-methyl

¹ H-NMR (CDCl ₃ ) δ: 1.29 (9H, s), 2.22 (3H, s), 6.74 (1H, s), 7.34 (2H, dd), 7.38 (2H, dd), 7.43 (1H, dd ), 8.72 (1H, d), 9.17 (1H, d).
Acetic acid = (4-tert-butylphenyl) -pyrimidin-4-yl-methyl (168 mg), triethylamine (0.13 ml), methanol (10 ml) and Pd carbon (catalytic amount) were mixed, and the mixture was stirred at room temperature for 9 hours under a hydrogen atmosphere of about 1 atm. Stir. The reaction mixture was filtered and then concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, so as to obtain 77 mg of 4- (4-tert-butylbenzyl) pyrimidine.
4- (4-tert-butylbenzyl) pyrimidine (Compound 1-1)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：１．３１（３Ｈ，ｔ），３．１４（２Ｈ，ｑ），６．６２（１Ｈ，ｄｄ），７．３３（１Ｈ，ｄｄ），７．６８（１Ｈ，ｄｄ），８．７６（１Ｈ，ｓ）．
４−クロロ−５−エチル−６−フラン−２−イル−ピリミジン３．０ｇ、ヒドラジン一水和物３．０ｇ、トリエチルアミン３．０ｇおよびＴＨＦ２０ｍｌの混合物を、加熱還流下２時間攪拌し、その混合物にヒドラジン一水和物１ｇを加え加熱還流下３時間攪拌した。反応混合物を室温まで放冷した後、反応混合物に水を注加し、酢酸エチルで抽出した。有機層を硫酸ナトリウムで乾燥させた後、減圧下濃縮し、（５−エチル−６−フラン−２−イル−ピリミジン−４−イル）−ヒドラジン２．８５ｇを得た。
（５−エチル−６−フラン−２−イル−ピリミジン−４−イル）−ヒドラジン

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：１．２６（３Ｈ，ｔ），２．７７（２Ｈ，ｑ），４．０９（２Ｈ，ｂｒｓ），６．２２（１Ｈ，ｂｒｓ），６．５６（１Ｈ，ｄｄ），７．１１（１Ｈ，ｄｄ），７．６０（１Ｈ，ｄｄ），８．５８（１Ｈ，ｓ）．
（５−エチル−６−フラン−２−イル−ピリミジン−４−イル）−ヒドラジン２．８５ｇ、アセトニトリル５０ｍｌおよび塩化パラトルエンスルホニル２．８６ｇの混合物に、氷冷下ピリジン２．３７ｇを加え室温で２時間攪拌した。反応混合物に水５０ｍｌを注加し、析出した固体をろ取した。この固体を水２０ｍｌとアセトニトリル２０ｍｌで順次洗浄し乾燥させた。得られた固体に水酸化ナトリウム８．１ｇ、エチレングリコール１００ｍｌおよび水５０ｍｌを加え、加熱還流下３時間攪拌した。反応混合物を室温まで放冷した後、反応混合物に水を注加し、酢酸エチルで抽出した。有機層を硫酸ナトリウムで乾燥させた後、減圧下濃縮した。残渣をシリカゲルカラムクロマトグラフィーに付し、５−エチル−４−フラン−２−イル−ピリミジン２．０３ｇを得た。
５−エチル−４−フラン−２−イル−ピリミジン

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：１．３１（３Ｈ，ｔ），２．９９（２Ｈ，ｑ），６．６１（１Ｈ，ｄｄ），７．２９（１Ｈ，ｄｄ），７．６７（１Ｈ，ｄｄ），８．５９（１Ｈ，ｓ），９．０４（１Ｈ，ｓ）．
５−エチル−４−フラン−２−イル−ピリミジン２．０３ｇ、アセトン７０ｍｌおよび水３５ｍｌの混合物５０℃で攪拌し、その混合物に過マンガン酸カリウム１５ｇを１５分間かけて加え、加熱還流下１時間攪拌した。反応混合物を室温まで放冷した後、反応混合物に飽和炭酸水素ナトリウム水溶液を注加し、ｔｅｒｔ−ブチルメチルエーテルで抽出した。得られた水層に塩酸を加え、ｔｅｒｔ−ブチルメチルエーテルで抽出し、有機層を硫酸ナトリウムで乾燥させた後、減圧下濃縮することで、５−エチル−ピリミジン−４−カルボン酸１．１４ｇを得た。
５−エチル−ピリミジン−４−カルボン酸

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：１．３３（３Ｈ，ｔ），３．２２（２Ｈ，ｑ），８．９０（１Ｈ，ｓ），９．１８（１Ｈ，ｓ）．
５−エチル−ピリミジン−４−カルボン酸３４１ｍｇ、Ｎ，Ｏ−ジメチルヒドロキシルアミン塩酸塩３２８ｍｇ、１−エチル−３−（３−ジメチルアミノプロピル）カルボジイミド塩酸塩８６１ｍｇ、１−ヒドロキシベンゾトリアゾール３０ｍｇ、トリエチルアミン１．５６ｍｌおよびクロロホルム６ｍｌの混合物を室温で４時間攪拌した。反応混合物に飽和塩化アンモニウム水溶液を注加した後、クロロホルムで抽出した。有機層を水洗した後、無水硫酸マグネシウムで乾燥し、減圧下に濃縮した。得られた残渣をシリカゲルクロマトグラフィーに付し、Ｎ−メトキシ−Ｎ−メチル−５−エチル−４−ピリミジンカルボキサミド４００ｍｇを得た。
Ｎ−メトキシ−Ｎ−メチル−５−エチル−４−ピリミジンカルボキサミド

¹H-NMR (CDCl₃) δ: 1.27 (3H, t), 2.66 (2H, q), 3.38 (3H, s), 3.61 (3H, s), 8.67 (1H, s), 9.07 (1H, s).
Ｎ−メトキシ−Ｎ−メチル−５−エチル−４−ピリミジンカルボキサミド３９５ｍｇとテトラヒドロフラン８ｍｌとの混合物に、４−ｔｅｒｔ−ブチルフェニルマグネシウムブロミド溶液（４−ｔｅｒｔ−ブチルフェニルブロミド２．５ｇ、マグネシウム０．３１ｇおよびテトラヒドロフラン１０ｍｌより調製した）５ｍｌを、氷冷下滴下した。室温で１時間攪拌した後、反応混合物に１規定塩酸および飽和炭酸水素ナトリウム水溶液を順次注加し、混合物を濾過した。得られた濾液を酢酸エチルで抽出した後、有機層を水洗し、無水硫酸マグネシウムで乾燥した。減圧下に濃縮後、シリカゲルクロマトグラフィーに付し、４−（４−ｔｅｒｔ−ブチルベンゾイル）−５−エチルピリミジン１２２ｍｇを得た。
４−（４−ｔｅｒｔ−ブチルベンゾイル）−５−エチルピリミジン

¹H-NMR (CDCl₃) δ: 1.24 (3H, t), 1.35 (9H, s), 2.71 (2H, q), 7.51 (2H, dd), 7.79 (2H, dd), 8.79 (1H, s), 9.15 (1H, s).
４−（４−ｔｅｒｔ−ブチルベンゾイル）−５−エチルピリミジン１２２ｍｇ、水素化ホウ素ナトリウム１７ｍｇおよびメタノール５ｍｌの混合物を室温で３時間攪拌した。反応混合物に飽和塩化アンモニウム水溶液を注加した後、酢酸エチルで抽出した。有機層を水洗した後、無水硫酸マグネシウムで乾燥し、減圧下に濃縮した。得られた残渣をシリカゲルクロマトグラフィーに付し、（４−ｔｅｒｔ−ブチルフェニル）−（５−エチルピリミジン−４−イル）−メタノール６９ｍｇを得た。
（４−ｔｅｒｔ−ブチルフェニル）−（５−エチルピリミジン−４−イル）−メタノール

¹H-NMR (CDCl₃) δ: 1.06 (3H, t), 1.28 (9H, s), 2.34-2.63 (2H, m), 5.38 (1H, d), 5.78 (1H, d), 7.16 (2H, dd), 7.33 (2H, dd), 8.51 (1H, s), 9.14 (1H, s).
（４−ｔｅｒｔ−ブチルフェニル）−（５−エチルピリミジン−４−イル）−メタノール６９ｍｇ、トリエチルアミン４３μｌおよびテトラヒドロフラン４ｍｌの混合物に、氷冷下、塩化アセチル１８μｌを加えた後、室温で５時間攪拌した。反応混合物に飽和炭酸水素ナトリウム水溶液を注加し、酢酸エチルで抽出した。有機層を水洗し、無水硫酸マグネシウムで乾燥した後、減圧下に濃縮し、酢酸＝（４−ｔｅｒｔ−ブチルフェニル）−（５−エチルピリミジン−４−イル）−メチル７４ｍｇを得た。
酢酸＝（４−ｔｅｒｔ−ブチルフェニル）−（５−エチルピリミジン−４−イル）−メチル

¹H-NMR (CDCl₃) δ: 1.22 (3H, t), 1.29 (9H, s), 2.19 (3H, s), 2.59-2.81 (2H, m), 6.85 (1H, s), 7.35-7.37 (4H, m), 8.52 (1H, s), 9.12 (1H, s).
酢酸＝（４−ｔｅｒｔ−ブチルフェニル）−（５−エチルピリミジン−４−イル）−メチル７４ｍｇ、トリエチルアミン５０μｌ、メタノール５ｍｌおよびＰｄ炭素（触媒量）を混合し、約１気圧の水素雰囲気下、室温で９時間攪拌した。反応混合物を濾過した後、減圧下に濃縮した。得られた残渣をシリカゲルクロマトグラフィーに付し、４−（４−ｔｅｒｔ−ブチルベンジル）−５−エチルピリミジン３５ｍｇを得た。
４−（４−ｔｅｒｔ−ブチルベンジル）−５−エチルピリミジン（化合物１−３３）

Production Example 8
A mixture of 10 g of 4,6-dichloro-5-ethylpyrimidine, 6.33 g of 2-furylboronic acid, 1.94 g of tetrakistriphenylphosphine palladium, 100 ml of dimethoxyethane and 60 ml of aqueous sodium carbonate solution (2 mol / l) And stirred at 80 ° C. for 2 hours. The reaction mixture was allowed to cool to room temperature, water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 6.06 g of 4-chloro-5-ethyl-6-furan-2-yl-pyrimidine.
4-Chloro-5-ethyl-6-furan-2-yl-pyrimidine

¹ H-NMR (CDCl ₃ ) δ: 1.31 (3H, t), 3.14 (2H, q), 6.62 (1H, dd), 7.33 (1H, dd), 7.68 ( 1H, dd), 8.76 (1H, s).
A mixture of 3.0 g of 4-chloro-5-ethyl-6-furan-2-yl-pyrimidine, 3.0 g of hydrazine monohydrate, 3.0 g of triethylamine and 20 ml of THF was stirred with heating under reflux for 2 hours. 1 g of hydrazine monohydrate was added to the mixture, and the mixture was stirred for 3 hours under reflux with heating. The reaction mixture was allowed to cool to room temperature, water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and then concentrated under reduced pressure to obtain 2.85 g of (5-ethyl-6-furan-2-yl-pyrimidin-4-yl) -hydrazine.
(5-Ethyl-6-furan-2-yl-pyrimidin-4-yl) -hydrazine

¹ H-NMR (CDCl ₃ ) δ: 1.26 (3H, t), 2.77 (2H, q), 4.09 (2H, brs), 6.22 (1H, brs), 6.56 ( 1H, dd), 7.11 (1H, dd), 7.60 (1H, dd), 8.58 (1H, s).
To a mixture of (5-ethyl-6-furan-2-yl-pyrimidin-4-yl) -hydrazine 2.85 g, acetonitrile 50 ml and paratoluenesulfonyl chloride 2.86 g, 2.37 g of pyridine was added at room temperature under ice cooling. Stir for 2 hours. 50 ml of water was poured into the reaction mixture, and the precipitated solid was collected by filtration. This solid was washed successively with 20 ml of water and 20 ml of acetonitrile and dried. To the obtained solid, 8.1 g of sodium hydroxide, 100 ml of ethylene glycol and 50 ml of water were added, and the mixture was stirred for 3 hours with heating under reflux. The reaction mixture was allowed to cool to room temperature, water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 2.03 g of 5-ethyl-4-furan-2-yl-pyrimidine.
5-Ethyl-4-furan-2-yl-pyrimidine

¹ H-NMR (CDCl ₃ ) δ: 1.31 (3H, t), 2.99 (2H, q), 6.61 (1H, dd), 7.29 (1H, dd), 7.67 ( 1H, dd), 8.59 (1H, s), 9.04 (1H, s).
A mixture of 2.03 g of 5-ethyl-4-furan-2-yl-pyrimidine, 70 ml of acetone and 35 ml of water was stirred at 50 ° C., 15 g of potassium permanganate was added to the mixture over 15 minutes, and the mixture was heated under reflux for 1 hour. Stir. The reaction mixture was allowed to cool to room temperature, saturated aqueous sodium hydrogen carbonate solution was poured into the reaction mixture, and the mixture was extracted with tert-butyl methyl ether. Hydrochloric acid was added to the obtained aqueous layer, and the mixture was extracted with tert-butyl methyl ether. The organic layer was dried over sodium sulfate and concentrated under reduced pressure to give 1.14 g of 5-ethyl-pyrimidine-4-carboxylic acid. Got.
5-ethyl-pyrimidine-4-carboxylic acid

¹ H-NMR (CDCl ₃ ) δ: 1.33 (3H, t), 3.22 (2H, q), 8.90 (1H, s), 9.18 (1H, s).
5-ethyl-pyrimidine-4-carboxylic acid 341 mg, N, O-dimethylhydroxylamine hydrochloride 328 mg, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride 861 mg, 1-hydroxybenzotriazole 30 mg, triethylamine 1 A mixture of .56 ml and 6 ml of chloroform was stirred at room temperature for 4 hours. A saturated aqueous ammonium chloride solution was poured into the reaction mixture, followed by extraction with chloroform. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 400 mg of N-methoxy-N-methyl-5-ethyl-4-pyrimidinecarboxamide.
N-methoxy-N-methyl-5-ethyl-4-pyrimidinecarboxamide

¹ H-NMR (CDCl ₃ ) δ: 1.27 (3H, t), 2.66 (2H, q), 3.38 (3H, s), 3.61 (3H, s), 8.67 (1H, s), 9.07 (1H, s ).
To a mixture of 395 mg of N-methoxy-N-methyl-5-ethyl-4-pyrimidinecarboxamide and 8 ml of tetrahydrofuran was added 4-tert-butylphenylmagnesium bromide solution (2.5 g of 4-tert-butylphenylbromide, 0.31 g of magnesium). And 5 ml of tetrahydrofuran (prepared from 10 ml of tetrahydrofuran) was added dropwise under ice cooling. After stirring at room temperature for 1 hour, 1N hydrochloric acid and saturated aqueous sodium hydrogen carbonate solution were sequentially added to the reaction mixture, and the mixture was filtered. The obtained filtrate was extracted with ethyl acetate, and then the organic layer was washed with water and dried over anhydrous magnesium sulfate. After concentration under reduced pressure, the residue was subjected to silica gel chromatography to obtain 122 mg of 4- (4-tert-butylbenzoyl) -5-ethylpyrimidine.
4- (4-tert-butylbenzoyl) -5-ethylpyrimidine

¹ H-NMR (CDCl ₃ ) δ: 1.24 (3H, t), 1.35 (9H, s), 2.71 (2H, q), 7.51 (2H, dd), 7.79 (2H, dd), 8.79 (1H, s ), 9.15 (1H, s).
A mixture of 122 mg of 4- (4-tert-butylbenzoyl) -5-ethylpyrimidine, 17 mg of sodium borohydride and 5 ml of methanol was stirred at room temperature for 3 hours. A saturated aqueous ammonium chloride solution was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, so as to obtain 69 mg of (4-tert-butylphenyl)-(5-ethylpyrimidin-4-yl) -methanol.
(4-tert-Butylphenyl)-(5-ethylpyrimidin-4-yl) -methanol

¹ H-NMR (CDCl ₃ ) δ: 1.06 (3H, t), 1.28 (9H, s), 2.34-2.63 (2H, m), 5.38 (1H, d), 5.78 (1H, d), 7.16 (2H , dd), 7.33 (2H, dd), 8.51 (1H, s), 9.14 (1H, s).
To a mixture of 69 mg of (4-tert-butylphenyl)-(5-ethylpyrimidin-4-yl) -methanol, 43 μl of triethylamine and 4 ml of tetrahydrofuran was added 18 μl of acetyl chloride under ice cooling, and the mixture was stirred at room temperature for 5 hours. . Saturated aqueous sodium hydrogen carbonate solution was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to obtain 74 mg of acetic acid = (4-tert-butylphenyl)-(5-ethylpyrimidin-4-yl) -methyl.
Acetic acid = (4-tert-butylphenyl)-(5-ethylpyrimidin-4-yl) -methyl

¹ H-NMR (CDCl ₃ ) δ: 1.22 (3H, t), 1.29 (9H, s), 2.19 (3H, s), 2.59-2.81 (2H, m), 6.85 (1H, s), 7.35-7.37 (4H, m), 8.52 (1H, s), 9.12 (1H, s).
Acetic acid = (4-tert-butylphenyl)-(5-ethylpyrimidin-4-yl) -methyl (74 mg), triethylamine (50 μl), methanol (5 ml) and Pd carbon (catalytic amount) were mixed, and the mixture was heated at room temperature under a hydrogen atmosphere of about 1 atm. For 9 hours. The reaction mixture was filtered and then concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, so as to obtain 35 mg of 4- (4-tert-butylbenzyl) -5-ethylpyrimidine.
4- (4-tert-butylbenzyl) -5-ethylpyrimidine (Compound 1-33)

¹H-NMR (CDCl₃) δ: 1.28 (9H, s), 3.89 (3H, s), 4.86 (1H, d), 5.95 (1H, d), 7.27-7.35 (4H, m), 8.27 (1H, s), 8.87 (1H, s).
（４−ｔｅｒｔ−ブチルフェニル）−（５−メトキシピリミジン−４−イル）−メタノール２７５ｍｇ、トリエチルアミン０．１７ｍｌおよびテトラヒドロフラン８ｍｌの混合物に、氷冷下、塩化アセチル７２μｌを加えた後、室温で５時間攪拌した。反応混合物に飽和炭酸水素ナトリウム水溶液を注加し、酢酸エチルで抽出した。有機層を水洗し、無水硫酸マグネシウムで乾燥した後、減圧下に濃縮し、酢酸＝（４−ｔｅｒｔ−ブチルフェニル）−（５−メトキシピリミジン−４−イル）−メチル３０８ｍｇを得た。
酢酸＝（４−ｔｅｒｔ−ブチルフェニル）−（５−メトキシピリミジン−４−イル）−メチル

¹H-NMR (CDCl₃) δ: 1.29 (9H, s), 2.20 (3H, s), 3.94 (3H, s), 6.99 (1H, s), 7.36 (2H, dd), 7.44 (2H, dd), 8.29 (1H, s), 8.86 (1H, s).
酢酸＝（４−ｔｅｒｔ−ブチルフェニル）−（５−メトキシピリミジン−４−イル）−メチル３０８ｍｇ、トリエチルアミン０．２１ｍｌ、メタノール１５ｍｌおよびＰｄ炭素（触媒量）を混合し、約１気圧の水素雰囲気下、室温で７時間攪拌した。反応混合物を濾過した後、減圧下に濃縮した。得られた残渣をシリカゲルクロマトグラフィーに付し、４−（４−ｔｅｒｔ−ブチルベンジル）−５−メトキシピリミジン１９９ｍｇを得た。
４−（４−ｔｅｒｔ−ブチルベンジル）−５−メトキシピリミジン（化合物１−３７）

Production Example 9
To a mixture of 833 mg of 2,2,6,6-tetramethylpiperidine and 50 ml of tetrahydrofuran, 3.7 ml of n-butyllithium (1.6M hexane solution) was added dropwise under ice cooling, followed by stirring for 30 minutes under ice cooling. did. Next, a mixture of 500 mg of 5-methoxypyrimidine and 10 ml of tetrahydrofuran was added dropwise at −70 ° C., and the mixture was stirred at −70 ° C. for 15 minutes. After adding 957 mg of 4-tert-butylbenzaldehyde dropwise at −70 ° C., the temperature was raised to room temperature, and water was poured into the reaction solution. The reaction mixture was extracted with ethyl acetate, the organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, so as to obtain 275 mg of (4-tert-butylphenyl)-(5-methoxypyrimidin-4-yl) -methanol.
(4-tert-Butylphenyl)-(5-methoxypyrimidin-4-yl) -methanol

¹ H-NMR (CDCl ₃ ) δ: 1.28 (9H, s), 3.89 (3H, s), 4.86 (1H, d), 5.95 (1H, d), 7.27-7.35 (4H, m), 8.27 (1H , s), 8.87 (1H, s).
To a mixture of 275 mg of (4-tert-butylphenyl)-(5-methoxypyrimidin-4-yl) -methanol, 0.17 ml of triethylamine and 8 ml of tetrahydrofuran was added 72 μl of acetyl chloride under ice cooling, and then at room temperature for 5 hours. Stir. Saturated aqueous sodium hydrogen carbonate solution was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 308 mg of acetic acid = (4-tert-butylphenyl)-(5-methoxypyrimidin-4-yl) -methyl.
Acetic acid = (4-tert-butylphenyl)-(5-methoxypyrimidin-4-yl) -methyl

¹ H-NMR (CDCl ₃ ) δ: 1.29 (9H, s), 2.20 (3H, s), 3.94 (3H, s), 6.99 (1H, s), 7.36 (2H, dd), 7.44 (2H, dd ), 8.29 (1H, s), 8.86 (1H, s).
Acetic acid = (4-tert-butylphenyl)-(5-methoxypyrimidin-4-yl) -methyl (308 mg), triethylamine (0.21 ml), methanol (15 ml) and Pd carbon (catalytic amount) were mixed, and hydrogen atmosphere at about 1 atm. And stirred at room temperature for 7 hours. The reaction mixture was filtered and then concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, so as to obtain 199 mg of 4- (4-tert-butylbenzyl) -5-methoxypyrimidine.
4- (4-tert-butylbenzyl) -5-methoxypyrimidine (Compound 1-37)

Production Example 10
A mixture of 150 mg of 4-tert-butylphenol, 179 mg of 4,6-dichloro-5-methoxypyrimidine, 358 mg of cesium carbonate and 3 ml of N-methylpyrrolidinone was stirred at 80 ° C. for 4 hours, and then stirred at 100 ° C. for 4 hours. Water was poured into the reaction mixture allowed to cool, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, so as to obtain 245 mg of 4- (4-tert-butylphenoxy) -6-chloro-5-methoxypyrimidine.
¹ H-NMR (CDCl ₃ ) δ: 1.35 (9H, s), 4.06 (3H, s), 7.09 (2H, dd), 7.46 (2H, dd), 8.26 (1H, s).
4- (4-tert-Butylphenoxy) -6-chloro-5-methoxypyrimidine (245 mg), ethyl acetate (10 ml), methanol (1 ml) and Pd carbon (catalytic amount) were mixed, and the mixture was mixed at about 1 atm of hydrogen atmosphere at room temperature for 15 hours. Stir. The reaction mixture was filtered and then concentrated under reduced pressure. Saturated aqueous sodium hydrogen carbonate solution was poured into the residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, so as to obtain 83 mg of 4- (4-tert-butylphenoxy) -5-methoxypyrimidine.
4- (4-tert-butylbenzyl) -5-methoxypyrimidine (Compound 2-13)

Production Example 11
A mixture of 2.00 g of 4,6-dichloro-5-nitropyrimidine, 1.55 g of 4-tert-butylphenol, 2.13 g of potassium carbonate and 4.5 ml of N, N-dimethylformamide was stirred at room temperature for 1 hour, Stir at 30 ° C. for 30 minutes. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was washed with n-hexane to obtain 1.93 g of 4- (4-tert-butylphenoxy) -6-chloro-5-nitropyrimidine.
¹ H-NMR (CDCl ₃ ) δ: 1.35 (9H, s), 7.10 (2H, dd), 7.47 (2H, dd), 8.60 (1H, s).
4- (4-tert-Butylphenoxy) -6-chloro-5-nitropyrimidine (1.73 g), triethylamine (2.5 ml), methanol (66 ml) and Pd carbon (catalytic amount) were mixed. Stir at 0 ° C. for 3 hours. The reaction mixture was filtered and then concentrated under reduced pressure. Saturated aqueous sodium hydrogen carbonate solution was poured into the residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, so as to obtain 845 mg of 4- (4-tert-butylphenoxy) -5-aminopyrimidine.
4- (4-tert-Butylphenoxy) -5-aminopyrimidine (Compound 2-33)

Production Example 12
A mixture of 270 mg of 4- (4-tert-butylphenoxy) -5-aminopyrimidine, 0.62 ml of acetaldehyde, 1.18 g of sodium triacetoxyborohydride, 1 drop of acetic acid and 6 ml of chloroform was stirred at 50 ° C. for 3 hours. A saturated aqueous sodium hydrogen carbonate solution was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, so as to obtain 297 mg of 4- (4-tert-butylphenoxy) -5-diethylaminopyrimidine.
4- (4-tert-Butylphenoxy) -5-diethylaminopyrimidine (Compound 2-31)

Production Example 13
To a mixture of 1.2 g of 2,2,6,6-tetramethylpiperidine and 10 ml of tetrahydrofuran, 5.3 ml of n-butyllithium (1.6 M hexane solution) was added dropwise at -10 ° C. Next, at -70 ° C, a mixture of 0.50 g of 5-ethoxypyrimidine and 10 ml of tetrahydrofuran was added dropwise to the reaction mixture, and the mixture was stirred at -70 ° C for 2 hours. Next, at -70 ° C, a mixture of 1.81 g of p-toluenesulfonyl azide and 10 ml of tetrahydrofuran was added dropwise to the reaction mixture, and the mixture was stirred at -70 ° C for 2 hours. Next, at −70 ° C., a mixture of 1 ml of concentrated hydrochloric acid and 2 ml of ethanol was added dropwise to the reaction mixture, and the temperature was raised to room temperature. Water was poured into the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with water, dried over sodium sulfate, and concentrated under reduced pressure to obtain 0.18 g of 4-azido-5-ethoxypyrimidine.
¹ H-NMR (CDCl ₃ ) δ: 1.61 (3H, t), 4.50 (2H, q), 7.79 (1H, s), 9.34 (1H, s).
To a mixture of 1.0 g of tin (II) chloride and 3 ml of concentrated hydrochloric acid, a mixture of 0.18 g of 4-azido-5-ethoxypyrimidine and 3 ml of methanol was added dropwise at room temperature. After stirring at room temperature for 0.5 hour, the reaction mixture was ice-cooled, and an aqueous sodium hydroxide solution and chloroform were added. The reaction mixture was filtered and the filtrate was separated. The organic layer was dried over sodium sulfate and concentrated under reduced pressure to give 0.10 g of 4-amino-5-ethoxypyrimidine.
¹ H-NMR (CDCl ₃ ) δ: 1.46 (3H, t), 4.12 (2H, q), 5.12 (2H, br s), 7.81 (1H, s), 8.23 (1H, s).
1-Bromo-4-tert-butylbenzene 0.18 g, 4-amino-5-ethoxypyrimidine 0.10 g, 1,4-dioxane 2 ml, sodium tert-butoxide 83 mg were mixed and purged with nitrogen. 10 mg of Pd ₂ (dba) ₃ and 25 mg of xanthophos were added, and the mixture was stirred at 100 ° C. for 8 hours. Water was poured into the cooled reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain N- (4-tert-butylphenyl) -5-ethoxypyrimidin-4-ylamine.
N- (4-tert-butylphenyl) -5-ethoxypyrimidin-4-ylamine (Compound 4-37)

Hereinafter, the compound manufactured by the manufacturing method according to the method as described in the above-mentioned Example manufacture example is illustrated.
In the table, Me is a methyl group (CH ₃ —), Et is an ethyl group (CH ₃ CH ₂ —), Pr is a propyl group (CH ₃ CH ₂ CH ₂ —), and i-Pr is an isopropyl group ((CH ₃ )). ₂ CH—), t-Bu represents a tert-butyl group ((CH ₃ ) ₃ C—), sec-Bu represents a sec-butyl group (CH ₃ CH ₂ CH (CH ₃ ) —), and Ph represents a phenyl group. .
In the table, the column “Substitution position” indicates the substitution position of A in the benzene ring in the formula.
In the table, when n is 1 in the column of “E _n ”, for example, “2-Me” is shown, which means that E is a methyl group substituted at the 2-position of the benzene ring. When n is 0, it is shown as “−”, which means that it is unsubstituted.

式中のＪ−Ｌ−Ａ基、Ｅ_n、Ｒ^x、Ｒ^y、Ｇ及びｍは、下記の〔表７〕〜〔表１２〕に記載の組み合わせを表す。 A compound represented by formula (A-1).

The JLA group, E _n , R ^x , R ^y , G and m in the formula represent the combinations described in the following [Table 7] to [Table 12].

式中のＪ−Ｌ−Ａ基、Ｅ_n、Ｇ及びｍは、下記の〔表１３〕〜〔表１６〕に記載の組み合わせを表す。 A compound represented by formula (A-2).

The JLA group, E _n , G and m in the formula represent the combinations described in the following [Table 13] to [Table 16].

式中のＪ−Ｌ−Ａ基、Ｅ_n、Ｇ、ｙ及びｍは、下記の〔表１７〕〜〔表２０〕に記載の組み合わせを表す。 A compound represented by formula (A-3).

The JLA group, E _n , G, y and m in the formula represent the combinations described in the following [Table 17] to [Table 20].

式中のＪ−Ｌ−Ａ基、Ｅ_n、Ｒ^z、Ｇ及びｍは、下記の〔表２１〕〜〔表２７〕に記載の組み合わせを表す。 A compound represented by formula (A-4).

The JLA group, E _n , R ^z , G and m in the formula represent the combinations described in the following [Table 21] to [Table 27].

The physical properties of the compounds of the present invention described in [Table 7] to [Table 27] are shown in [Table 28] to [Table 30] below.

  Next, the formulation example of this invention compound is shown. In addition, a part represents a weight part.

Formulation Example 1
10 parts of any one of the above compounds 1-1 to 1-127, compounds 2-1 to 2-89, compounds 3-1 to 3-81, or compounds 4-1 to 4-174 and 35 parts of xylene Dissolve in a mixture with 35 parts of N, N-dimethylformamide, add 14 parts of polyoxyethylene styryl phenyl ether and 6 parts of calcium dodecylbenzenesulfonate and mix to obtain each emulsion.

Formulation Example 2
4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, 20 parts of synthetic silicon hydrous fine powder and 54 parts of diatomaceous earth are mixed, and the above-mentioned compounds 1-1 to 1-127, compounds 2-1 to 2-89, 20 parts of any one of compounds 3-1 to 3-81 or compounds 4-1 to 4-174 are added and mixed to obtain each wettable powder.

Formulation Example 3
Any one of the above-mentioned compounds 1-1 to 1-127, compounds 2-1 to 2-89, compounds 3-1 to 3-81, or compounds 4-1 to 4-174, and 2 parts Add 1 part fine powder, 2 parts calcium lignin sulfonate, 30 parts bentonite and 65 parts kaolin clay and mix. Next, an appropriate amount of water is added to the mixture, and the mixture is further stirred, granulated by a granulator, and dried by ventilation to obtain each granule.

Formulation Example 4
Any one of the above-mentioned compounds 1-1 to 1-127, compounds 2-1 to 2-89, compounds 3-1 to 3-81 or compounds 4-1 to 4-174 1 part in an appropriate amount of acetone Dissolve it, add 5 parts of synthetic hydrous silicon oxide fine powder, 0.3 part of PAP, and 93.7 parts of fusami clay, stir and mix thoroughly, and evaporate and remove acetone to obtain each powder.

Formulation Example 5
35 parts of a mixture of polyoxyethylene alkyl ether sulfate ammonium salt and white carbon (weight ratio 1: 1), the above-mentioned compounds 1-1 to 1-127, compounds 2-1 to 2-89, compounds 3-1 to 3 -81 or 10 parts of any one of compounds 4-1 to 4-174 and 55 parts of water are mixed and pulverized by a wet pulverization method to obtain each preparation.

Formulation Example 6
Any one of the above compounds 1-1 to 1-127, compounds 2-1 to 2-89, compounds 3-1 to 3-81, or compounds 4-1 to 4-174 0.1 part of xylene 5 parts And dissolved in 5 parts of trichloroethane and mixed with 89.9 parts of deodorized kerosene to obtain each oil.

Formulation Example 7
10 mg of any one of the above-mentioned compounds 1-1 to 1-127, compounds 2-1 to 2-89, compounds 3-1 to 3-81, or compounds 4-1 to 4-174 is dissolved in 0.5 ml of acetone. Then, this solution is treated with 5 g of animal solid feed powder (solid feed powder CE-2 for breeding, product of Nippon Claire Co., Ltd.) and mixed uniformly. Then, acetone is evaporated to dryness to obtain each poisonous bait.

Formulation Example 8
0.1 part of any one of the above-mentioned compounds 1-1 to 1-127, compounds 2-1 to 2-89, compounds 3-1 to 3-81 or compounds 4-1 to 4-174, neothiozole (center Kasei Co., Ltd.) After putting 49.9 parts in an aerosol can and mounting an aerosol valve, 25 parts of dimethyl ether and 25 parts of LPG are added and shaken, and an oil aerosol is obtained by mounting an actuator.

Formulation Example 9
0.6 part of any one of the aforementioned compounds 1-1 to 1-127, compounds 2-1 to 2-89, compounds 3-1 to 3-81 or compounds 4-1 to 4-174, BHT (2 , 6-Di-tert-butyl-4-methylphenol), 0.01 part of xylene, 5 parts of xylene, 3.39 parts of deodorized kerosene and 1 part of emulsifier {Atmos 300 (registered trademark of Atmos Chemical)} Then, 50 parts of distilled water is filled into an aerosol container, and a valve is mounted. Then, 40 parts of a propellant (LPG) is pressurized and filled through the valve to obtain an aqueous aerosol.

Formulation Example 10
5 parts of any one of the above-mentioned compounds 1-1 to 1-127, compounds 2-1 to 2-89, compounds 3-1 to 3-81 or compounds 4-1 to 4-174 and 5 parts of ferrimzone In addition, 4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, 20 parts of synthetic silicon hydroxide-containing fine powder and the remainder of diatomaceous earth are mixed and mixed well to obtain 100 parts of wettable powder.

Formulation Examples 11-25
It replaces with 5 parts of ferrimzone, and except having applied with each compound and usage-amount of the [Table 31] description, operation similar to the formulation example 10 is performed, and 100 parts of each wettable powder is obtained.

  Next, test examples are shown.

Test example 1
The preparation of the compound of the present invention obtained in Formulation Example 5 was diluted with water so that the active ingredient concentration was 500 ppm to prepare a test drug solution.
10 ml of the test chemical solution was sprayed on rice seedlings in the second leaf development stage planted in a polyethylene cup. After air drying, 20 3-4 instar larvae of the brown planthopper were released and stored in a greenhouse at 25 ° C. Six days later, the number of brown planthoppers infested with rice was investigated, and the control value was determined by the following formula.
Control value (%) = {1− (Cb × Tai) / (Cai × Tb)} × 100
In addition, the character in a formula represents the following meaning.
Cb: number of insects before treatment in the untreated group Cai: number of insects when observed in the untreated group Tb: number of insects before treatment in the treated group Tai: number of insects when observed in the treated group As a result, the following compounds of the present invention The treatment group of the spray liquid for the test showed a control value of 90% or more.

Compounds 1-1, 1-37, 1-41, 2-1, 11-1, 2-13, 2-31, 2-33, 2-34, 2-35, 2-36, 2-37, 3 -17, 3-19, 4-21, 4-22, 4-33, 4-34, 4-37.
Moreover, as a result of conducting the same test using the test chemical solution having an active ingredient concentration of 200 ppm, the treatment group of the test spray solution of the following compound of the present invention showed a control value of 90% or more.

Compounds 1-33, 2-9, 3-1, 4-1.

Test example 2
The preparation of the compound of the present invention obtained in Formulation Example 5 was diluted with water so that the active ingredient concentration was 500 ppm to prepare a test spray solution.
On the other hand, about 30 cotton aphids were inoculated into cucumber seedlings (first true leaf development stage) planted in plastic cups and left for 1 day. Each of these seedlings was sprayed with 20 ml of the diluted solution.
Six days after spraying, the number of live cotton aphids that parasitized on the leaves of the cucumber was examined, and the control value was determined by the following formula.
Control value (%) = {1− (Cb × Tai) / (Cai × Tb)} × 100
In addition, the character in a formula represents the following meaning.
Cb: number of insects before treatment in the untreated group Cai: number of insects when observed in the untreated group Tb: number of insects before treatment in the treated group Tai: number of insects when observed in the treated group As a result, the following compounds of the present invention The treatment group of the spray liquid for the test showed a control value of 90% or more.

Compounds 1-1, 1-37, 1-41, 2-11, 2-13, 2-31, 2-36, 3-17, 3-19, 4-22, 4-33, 4-34, 4 -37.

  The compound of the present invention is useful for controlling pests.

Claims (14)

Formula (1)

[Where,
J is the following formula J1 or J2

(Where
R ¹ and R ² are the same or different and each represents a C1-C3 alkyl group optionally having one or more halogen atoms,
R ³ represents a C1-C6 chain hydrocarbon group which may have one or more halogen atoms, a halogen atom or a hydrogen atom,
R ⁴ and R ⁵ are the same or different and represent a C1-C3 alkyl group,
R ⁶ represents a hydrogen atom or a C1-C6 chain hydrocarbon group. ) Represents a group represented by
L represents a single bond or a C1-C3 alkylene group which may have one or more halogen atoms,
A is bonded to the 3-position or 4-position of the benzene ring of the formula (1) and represents a single bond, —O—, or —S (O) _x — (where x is 0, 1 or 2). Represents)
Q is the following formula Q1, Q2, Q3 or Q4

(Where
R ^x and R ^y are the same or different and each may have one or more atoms or groups selected from group α, a C1-C6 chain hydrocarbon group, cyano group, halogen atom, hydrogen atom or cyclo Represents a propyl group,
y represents 0, 1 or 2;
R ^z is a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from the group α, —C (O) —T ¹ , —S (O) ₂ —T ^2. Represents a hydrogen atom or a cyclopropyl group,
T ¹ has a C1-C6 alkyl group optionally having one or more halogen atoms, a C1-C6 alkoxy group optionally having one or more halogen atoms, and having one or more halogen atoms. An optionally substituted C1-C6 alkylamino group, an optionally substituted C2-C12 dialkylamino group, a hydroxyl group, an amino group, a hydrogen atom or a cyclopropyl group,
T ² represents a C1-C6 alkyl group which may have one or more halogen atoms. ) Represents a group represented by
G represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a mercapto group or an amino group, or G 1, G 2, G 3 or G 4

{Where,
R ^a represents a C1-C6 chain hydrocarbon group, a cyclopropyl group or —C (O) —T ¹ which may have one or more atoms or groups selected from the group β,
R ^b is a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from the group γ, —C (O) —T ¹ , —S (O) ₂ —T ^2. Represents a C3-C9 trialkylsilyl group or a cyclopropyl group,
R ^c represents a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from the group γ, —C (O) —T ¹ or a cyclopropyl group (where, T ¹ is as defined above, but when G is G2, G3 or G4, T ¹ is a C1-C6 alkyl group optionally having one or more halogen atoms, one or more halogens. C1-C6 alkoxy group which may have an atom, C1-C6 alkylamino group which may have one or more halogen atoms, C2-C12 which may have one or more halogen atoms A dialkylamino group, an amino group, a hydrogen atom or a cyclopropyl group).
z represents 0, 1 or 2;
R ^d is a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from the group γ, —C (O) —T ¹ , —S (O) ₂ —T ^2. Or a cyclopropyl group (wherein T ¹ and T ² are as defined above),
R ^e represents a C1-C6 chain hydrocarbon group, a hydrogen atom or a cyclopropyl group which may have one or more atoms or groups selected from the group γ. } Represents a group represented by
m represents 0 or 1;
E represents a C1-C2 alkyl group which may have one or more halogen atoms or a halogen atom,
n represents 0, 1, 2, 3 or 4;
However, when n is 2, 3 or 4, each E may be different from each other.
Group α: a group consisting of a halogen atom, a cyano group and a cyclopropyl group.
Group β: C1-C4 alkoxy group optionally having one or more halogen atoms, C1-C4 alkylthio group optionally having one or more halogen atoms, having one or more halogen atoms C1-C4 alkylsulfinyl group which may have one, C1-C4 alkylsulfonyl group which may have one or more halogen atoms, C1-C4 alkylamino group which may have one or more halogen atoms A group consisting of a C2-C8 dialkylamino group optionally having one or more halogen atoms, a halogen atom, a cyano group, a C3-C9 trialkylsilyl group and a cyclopropyl group.
Group γ: C1-C4 alkoxy group optionally having one or more halogen atoms, C1-C4 alkylthio group optionally having one or more halogen atoms, having one or more halogen atoms C1-C4 alkylsulfinyl group which may have one, C1-C4 alkylsulfonyl group which may have one or more halogen atoms, C1-C4 alkylamino group which may have one or more halogen atoms A C2-C8 dialkylamino group or a phenyl group which may have one or more halogen atoms (the phenyl group may have a methyl group, a methoxy group, a chlorine atom or a nitro group), A group consisting of a halogen atom, a cyano group, a C3-C9 trialkylsilyl group and a cyclopropyl group.
However, Q is Q4, ^Rz is a hydrogen atom, G is a hydrogen atom, n is 0, the substitution position of the A group is the 4-position of the benzene ring, A is a single bond, When J is J1, R ¹ and R ² are both ethyl groups, and R ³ is a hydrogen atom, L represents a single bond or a C1-C3 alkylene group. ]
The pyrimidine compound shown by these.   The pyrimidine compound according to claim 1, wherein Q is Q1.   The pyrimidine compound according to claim 1, wherein Q is Q2, Q3 or Q4.   The pyrimidine compound according to claim 1, wherein Q is Q2.   The pyrimidine compound according to claim 1, wherein Q is Q3.   The pyrimidine compound according to claim 1, wherein Q is Q4.   The pyrimidine compound according to claim 1, wherein L is a single bond or a C1-C3 alkylene group.   The pyrimidine compound according to claim 1, wherein G is a hydrogen atom, a halogen atom, G1, G2, G3 or G4.   The pyrimidine compound according to claim 1, wherein G is G1, G2, G3 or G4.   The pyrimidine compound according to claim 1, wherein G is G2 or G3.   The pyrimidine compound according to claim 1, wherein G is G1 or G4.   A pest control agent comprising the pyrimidine compound according to any one of claims 1 to 11 and an inert carrier.   Use of the pyrimidine compound according to any one of claims 1 to 11 for controlling pests.   A method for controlling pests, comprising a step of applying an effective amount of the pyrimidine compound according to any one of claims 1 to 11 to pests or habitats of pests.