JP2012087059A - Noxious animal controlling composition and controlling method of noxious animal - Google Patents

Abstract

〔式中、Ｑ、Ｇ¹、Ｒ¹、Ｒ²、Ｒ³は明細書に記載の定義を表す。〕で示されるピリミジン化合物と、クロルピリホス、クロルピリホスメチル、アセフェート、メタミドフォス、メチダチオン及びフェニトロチオンからなる群より選ばれる少なくとも１種の有機リン化合物とを含有する有害動物防除組成物。
【選択図】なしProvided are a composition for controlling harmful animals having an excellent controlling effect on harmful animals, and a method for controlling harmful animals.
SOLUTION: Formula (1)

[Wherein, Q, G ¹ , R ¹ , R ² , R ³ represent the definitions described in the specification. ] The pest control composition containing the pyrimidine compound shown by these, and at least 1 sort (s) of organic phosphorus compound chosen from the group which consists of chlorpyrifos, chlorpyrifosmethyl, acephate, methamidophos, methidathion, and fenitrothion.
[Selection figure] None

Description

  The present invention relates to a pest control composition and a pest control method.

  So far, various compounds have been studied and put into practical use for the purpose of controlling pests.

The Pesticide Manual-15th edition (BCPC); ISBN 978-1-901396-18-8

  An object of the present invention is to provide a pest control composition having an excellent control effect on harmful animals, and a method for controlling harmful animals.

〔式中、
Ｑは酸素または硫黄を表し、
Ｇ¹は窒素またはＣＨを表し、
Ｒ¹は水素またはアミノ基を表し、
Ｒ²は水素、ハロゲン、ニトロ基、アミノ基、シアノ基、ハロゲンで置換されていてもよいＣ１−Ｃ６鎖状炭化水素基、ハロゲンで置換されていてもよいＣ３−Ｃ６シクロアルキル基、ハロゲンで置換されていてもよいＣ１−Ｃ６アルコキシ基、ハロゲンで置換されていてもよいＣ１−Ｃ４アルキルアミノ基またはハロゲンで置換されていてもよいＣ２−Ｃ８ジアルキルアミノ基を表し、
Ｒ³は群Ａより選ばれる１個以上の基で置換されたＣ１−Ｃ６アルキル基または群Ａより選ばれる１個以上の基で置換されたＣ３−Ｃ６アルケニル基を表し、
群Ａはハロゲンおよび−Ｓｉ（Ｒ⁴）₃
｛Ｒ⁴は互いに同一でも相異なっていてもよく、ハロゲンで置換されていてもよいＣ１−Ｃ６鎖状炭化水素基を表す。｝からなる群を表す。〕
で示されるピリミジン化合物と、クロルピリホス、クロルピリホスメチル、アセフェート、メタミドホス、メチダチオン及びフェニトロチオンからなる群より選ばれる少なくとも１種の有機リン化合物とを含有する有害動物防除組成物。
［２］ 式（１）における、Ｑが酸素である［１］記載の有害動物防除組成物。
［３］ 式（１）における、Ｒ²が水素、ハロゲンまたはハロゲンで置換されていてもよいＣ１−Ｃ６アルキル基である［１］又は［２］記載の有害動物防除組成物。
［４］ 式（１）における、Ｒ²が水素又はハロゲンで置換されていてもよいＣ１−Ｃ６アルキル基である［１］又は［２］記載の有害動物防除組成物。
［５］ 式（１）における、Ｒ¹が水素である［１］〜［４］いずれか一項記載の有害動物防除組成物。
［６］ 式（１）における、Ｒ³がハロゲンで置換されたＣ１−Ｃ６アルキル基またはハロゲンで置換されたＣ３−Ｃ６アルケニル基である［１］〜［５］いずれか一項記載の有害動物防除組成物。
［７］ 式（１）における、Ｒ³がハロゲンで置換されたＣ１−Ｃ６アルキル基である［１］〜［５］いずれか一項記載の有害動物防除組成物。
［８］ 式（１）における、Ｒ³が１個〜８個のフッ素または塩素で置換されたＣ１−Ｃ６アルキル基である［１］〜［５］いずれか一項記載の有害動物防除組成物。
［９］ 式（１）における、Ｇ¹が窒素である［１］〜［８］いずれか一項記載の有害動物防除組成物。
［１０］ ピリミジン化合物と有機リン化合物との重量比が、５：９５〜９５：５の［１］〜［９］いずれか一項記載の有害動物防除組成物。
［１１］ 式（Ａ）

〔式中、
Ｒ^2Aは水素、Ｃ１−Ｃ３アルキル又はハロゲンを表し、
Ｒ^3Aはハロゲンで置換されていてもよいＣ１−Ｃ６アルキル基又はハロゲンで置換されていてもよいＣ３−Ｃ６アルケニル基を表す。〕
で示されるピリミジン化合物と、クロルピリホス、クロルピリホスメチル、アセフェート、メタミドホス、メチダチオン及びフェニトロチオンからなる群より選ばれる少なくとも１種の有機リン化合物とを含有する有害動物防除組成物。
［１２］ ピリミジン化合物と有機リン化合物との重量比が、５：９５〜９５：５の［１１］記載の有害動物防除組成物。
［１３］
式（１）

〔式中、
Ｑは酸素または硫黄を表し、
Ｇ¹は窒素またはＣＨを表し、
Ｒ¹は水素またはアミノ基を表し、
Ｒ²は水素、ハロゲン、ニトロ基、アミノ基、シアノ基、ハロゲンで置換されていてもよいＣ１−Ｃ６鎖状炭化水素基、ハロゲンで置換されていてもよいＣ３−Ｃ６シクロアルキル基、ハロゲンで置換されていてもよいＣ１−Ｃ６アルコキシ基、ハロゲンで置換されていてもよいＣ１−Ｃ４アルキルアミノ基またはハロゲンで置換されていてもよいＣ２−Ｃ８ジアルキルアミノ基を表し、
Ｒ³は群Ａより選ばれる１個以上の基で置換されたＣ１−Ｃ６アルキル基または群Ａより選ばれる１個以上の基で置換されたＣ３−Ｃ６アルケニル基を表し、
群Ａはハロゲンおよび−Ｓｉ（Ｒ⁴）₃
｛Ｒ⁴は互いに同一でも相異なっていてもよく、ハロゲンで置換されていてもよいＣ１−Ｃ６鎖状炭化水素基を表す。｝からなる群を表す。〕
で示されるピリミジン化合物と、クロルピリホス、クロルピリホスメチル、アセフェート、メタミドホス、メチダチオン及びフェニトロチオンからなる群より選ばれる少なくとも１種の有機リン化合物との有効量を、有害動物または有害動物の生息場所に施用する有害動物の防除方法。
［１４］ 式（１）における、Ｑが酸素である［１３］記載の防除方法。
［１５］ 式（１）における、Ｒ²が水素、ハロゲンまたはハロゲンで置換されていてもよいＣ１−Ｃ６アルキル基である［１３］又は［１４］記載の防除方法。
［１６］ 式（１）における、Ｒ²が水素又はハロゲンで置換されていてもよいＣ１−Ｃ６アルキル基である［１３］又は［１４］記載の防除方法。
［１７］ 式（１）における、Ｒ¹が水素である［１３］〜［１６］いずれか一項記載の防除方法。
［１８］ 式（１）における、Ｒ³がハロゲンで置換されたＣ１−Ｃ６アルキル基またはハロゲンで置換されたＣ３−Ｃ６アルケニル基である［１３］〜［１７］いずれか一項記載の防除方法。
［１９］ 式（１）における、Ｒ³がハロゲンで置換されたＣ１−Ｃ６アルキル基である［１３］〜［１７］いずれか一項記載の防除方法。
［２０］ 式（１）における、Ｒ³が１個〜８個のフッ素または塩素で置換されたＣ１−Ｃ６アルキル基である［１３］〜［１７］いずれか一項記載の防除方法。
［２１］ 式（１）における、Ｇ¹が窒素である［１３］〜［２０］いずれか一項記載の防除方法。
［２２］ ピリミジン化合物と有機リン化合物との重量比が、５：９５〜９５：５の［１３］〜［２１］いずれか一項記載の防除方法。
［２３］ 式（Ａ）

〔式中、
Ｒ^2Aは水素、Ｃ１−Ｃ３アルキル又はハロゲンを表し、
Ｒ^3Aはハロゲンで置換されていてもよいＣ１−Ｃ６アルキル基又はハロゲンで置換されていてもよいＣ３−Ｃ６アルケニル基を表す。〕
で示されるピリミジン化合物と、クロルピリホス、クロルピリホスメチル、アセフェート、メタミドホス、メチダチオン及びフェニトロチオンからなる群より選ばれる少なくとも１種の有機リン化合物との有効量を、有害動物または有害動物の生息場所に施用する有害動物の防除方法。
［２４］ ピリミジン化合物と有機リン化合物との重量比が、５：９５〜９５：５の［２３］記載の防除方法。 As a result of intensive studies, the present inventors have determined that a pyrimidine compound represented by the following formula (1) and at least one organic phosphorus compound selected from the group consisting of chlorpyrifos, chlorpyrifosmethyl, acephate, methamidophos, metidathion, and fenitrothion. By using together, it discovered that it had the outstanding control effect with respect to a harmful animal, and resulted in this invention.
That is, the present invention has the following configuration.
[1] Formula (1)

[Where,
Q represents oxygen or sulfur,
G ¹ represents nitrogen or CH,
R ¹ represents hydrogen or an amino group,
R ² is hydrogen, halogen, nitro group, amino group, cyano group, C1-C6 chain hydrocarbon group optionally substituted with halogen, C3-C6 cycloalkyl group optionally substituted with halogen, halogen, A C1-C6 alkoxy group which may be substituted, a C1-C4 alkylamino group which may be substituted with a halogen, or a C2-C8 dialkylamino group which may be substituted with a halogen,
R ³ represents a C1-C6 alkyl group substituted with one or more groups selected from group A or a C3-C6 alkenyl group substituted with one or more groups selected from group A;
Group A is a halogen and -Si (R ⁴⁾ ₃
{R ⁴ may be the same or different from each other, and represents a C1-C6 chain hydrocarbon group which may be substituted with halogen. } Represents a group consisting of. ]
And a pesticide composition comprising at least one organic phosphorus compound selected from the group consisting of chlorpyrifos, chlorpyrifosmethyl, acephate, methamidophos, methidathion and fenitrothion.
[2] The pest control composition according to [1], wherein Q in formula (1) is oxygen.
[3] The pest control composition according to [1] or [2], wherein R ² in formula (1) is hydrogen, halogen, or a C1-C6 alkyl group optionally substituted with halogen.
[4] The pest control composition according to [1] or [2], wherein R ² in formula (1) is a C1-C6 alkyl group optionally substituted with hydrogen or halogen.
[5] The pest control composition according to any one of [1] to [4], wherein R ¹ in formula (1) is hydrogen.
[6] The pest according to any one of [1] to [5], wherein in formula (1), R ³ is a C1-C6 alkyl group substituted with halogen or a C3-C6 alkenyl group substituted with halogen. Control composition.
[7] The pest control composition according to any one of [1] to [5], wherein R ³ in formula (1) is a C1-C6 alkyl group substituted with halogen.
[8] The pest control composition according to any one of [1] to [5], wherein R ³ in formula (1) is a C1-C6 alkyl group substituted with 1 to 8 fluorine or chlorine. .
[9] The pest control composition according to any one of [1] to [8], wherein G ¹ in formula (1) is nitrogen.
[10] The pest control composition according to any one of [1] to [9], wherein the weight ratio of the pyrimidine compound and the organophosphorus compound is 5:95 to 95: 5.
[11] Formula (A)

[Where,
R ^2A represents hydrogen, C1-C3 alkyl or halogen;
R ^3A represents a C1-C6 alkyl group which may be substituted with halogen or a C3-C6 alkenyl group which may be substituted with halogen. ]
And a pesticide composition comprising at least one organic phosphorus compound selected from the group consisting of chlorpyrifos, chlorpyrifosmethyl, acephate, methamidophos, methidathion and fenitrothion.
[12] The pest control composition according to [11], wherein the weight ratio of the pyrimidine compound and the organophosphorus compound is 5:95 to 95: 5.
[13]
Formula (1)

[Where,
Q represents oxygen or sulfur,
G ¹ represents nitrogen or CH,
R ¹ represents hydrogen or an amino group,
R ² is hydrogen, halogen, nitro group, amino group, cyano group, C1-C6 chain hydrocarbon group optionally substituted with halogen, C3-C6 cycloalkyl group optionally substituted with halogen, halogen, A C1-C6 alkoxy group which may be substituted, a C1-C4 alkylamino group which may be substituted with a halogen, or a C2-C8 dialkylamino group which may be substituted with a halogen,
R ³ represents a C1-C6 alkyl group substituted with one or more groups selected from group A or a C3-C6 alkenyl group substituted with one or more groups selected from group A;
Group A is a halogen and -Si (R ⁴⁾ ₃
{R ⁴ may be the same or different from each other, and represents a C1-C6 chain hydrocarbon group which may be substituted with halogen. } Represents a group consisting of. ]
A harmful effect in which an effective amount of the pyrimidine compound represented by the above formula and at least one organophosphorus compound selected from the group consisting of chlorpyrifos, chlorpyrifosmethyl, acephate, methamidophos, methidathion and fenitrothion is applied to harmful animals or habitats of harmful animals Animal control methods.
[14] The control method according to [13], wherein Q in formula (1) is oxygen.
[15] The control method according to [13] or [14], wherein in formula (1), R ² is hydrogen, halogen or a C1-C6 alkyl group optionally substituted with halogen.
[16] The control method according to [13] or [14], wherein R ² in formula (1) is a C1-C6 alkyl group optionally substituted with hydrogen or halogen.
[17] The control method according to any one of [13] to [16], wherein R ¹ in formula (1) is hydrogen.
[18] The control method according to any one of [13] to [17], wherein in formula (1), R ³ is a C1-C6 alkyl group substituted with halogen or a C3-C6 alkenyl group substituted with halogen. .
[19] The control method according to any one of [13] to [17], wherein in Formula (1), R ³ is a C1-C6 alkyl group substituted with a halogen.
[20] The control method according to any one of [13] to [17], wherein in formula (1), R ³ is a C1-C6 alkyl group substituted with 1 to 8 fluorine or chlorine.
[21] The control method according to any one of [13] to [20], wherein G ¹ in the formula (1) is nitrogen.
[22] The control method according to any one of [13] to [21], wherein the weight ratio of the pyrimidine compound to the organophosphorus compound is 5:95 to 95: 5.
[23] Formula (A)

[Where,
R ^2A represents hydrogen, C1-C3 alkyl or halogen;
R ^3A represents a C1-C6 alkyl group which may be substituted with halogen or a C3-C6 alkenyl group which may be substituted with halogen. ]
A harmful effect in which an effective amount of the pyrimidine compound represented by the above formula and at least one organophosphorus compound selected from the group consisting of chlorpyrifos, chlorpyrifosmethyl, acephate, methamidophos, methidathion and fenitrothion is applied to harmful animals or habitats of harmful animals Animal control methods.
[24] The control method according to [23], wherein the weight ratio of the pyrimidine compound and the organophosphorus compound is 5:95 to 95: 5.

  The pest control composition according to the present invention has an excellent control effect on pests.

  The pest control composition according to the present invention (hereinafter sometimes referred to as “the present composition”) may be referred to as a pyrimidine compound represented by the formula (1) (hereinafter referred to as “the present active compound”). ) And at least one organic phosphorus compound selected from the group consisting of chloropyrifos, chloropyrifosmethyl, acephate, methamidophos, methidathion and fenitrothion (hereinafter sometimes referred to as “the present organic phosphorus compound”) as active ingredients. To do.

The active compound will be described.
Examples of the substituent in the active compound include the following. In the present invention, “halogen atom” means a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

In the active compound, examples of the “C1-C6 chain hydrocarbon group” include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, and an isopentyl group. A C1-C6 alkyl group such as a group, 1-methylbutyl group, tert-pentyl group, neopentyl group, hexyl group, isohexyl group;
C2-C6 such as vinyl group, 2-propenyl group, 2-butenyl group, 3-butenyl group, 2-methyl-2-propenyl group, 3-methyl-2-butenyl group, 2-pentenyl group and 2-hexenyl group An alkenyl group;
Examples include C2-C6 alkynyl groups such as ethynyl group, 2-propynyl group, 2-butynyl group and 3-butynyl group.

Examples of the “C1-C6 chain hydrocarbon group optionally substituted with halogen” in the active compound include, for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert group -Butyl group, pentyl group, isopentyl group, 1-methylbutyl group, tert-pentyl group, neopentyl group, hexyl group, isohexyl group, fluoromethyl group, difluoromethyl group, trifluoromethyl group, 2,2,2- A C1-C6 alkyl group optionally substituted with a halogen such as a trifluoroethyl group, 2,2,2-trichloroethyl group, pentafluoroethyl group, perfluoropropyl group, perfluorobutyl group, perfluorohexyl group;
Vinyl group, 2-propenyl group, 3-chloro-2-propenyl group, 2-chloro-2-propenyl group, 3,3-dichloro-2-propenyl group, 2-butenyl group, 3-butenyl group, 2-methyl A C2-C6 alkenyl group optionally substituted with halogen such as a 2-propenyl group, a 3-methyl-2-butenyl group, a 2-pentenyl group and a 2-hexenyl group;
C2-C6 alkynyl group optionally substituted with halogen such as ethynyl group, 2-propynyl group, 2-butynyl group, 3-butynyl group, 3-chloro-2-propynyl group and 3-bromo-2-propynyl group Is mentioned.

  In this active compound, examples of the “C3-C6 cycloalkyl group optionally substituted with halogen” include a cyclopropyl group, a 2,2-difluorocyclopropyl group, a 2,2-dichlorocyclopropyl group, a 2,2- Examples thereof include a dibromocyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.

  In this active compound, examples of the “C1-C6 alkoxy group optionally substituted with halogen” include a methoxy group, a trifluoromethoxy group, an ethoxy group, a 2,2,2-trifluoroethoxy group, a propyloxy group, and an isopropyl group. Examples thereof include an oxy group, a butoxy group, an isobutyloxy group, a sec-butyloxy group, a tert-butyloxy group, a pentyloxy group, and a hexyloxy group.

  Examples of the “C1-C4 alkylamino group optionally substituted with halogen” in the present active compound include a methylamino group, an ethylamino group, a 2,2,2-trifluoroethylamino group, a propylamino group, and an isopropylamino group. Groups and butylamino groups.

  Examples of the “C2-C8 dialkylamino group optionally substituted with halogen” in the present active compound include a dimethylamino group, a diethylamino group, a bis (2,2,2-trifluoroethyl) amino group, and a dipropylamino group. Groups.

  In the present active compound, examples of the “C1-C6 alkyl group substituted by one or more groups selected from group A” include 2,2-dichloropropyl group, 2-chloro-2-methylpropyl group, 2,2 , 2-trichloroethyl group, 1-methyl-2,2,2-trichloroethyl group, monofluoromethyl group, difluoromethyl group, trifluoromethyl group, 1,1-difluoroethyl group, 2,2-difluoroethyl group 1,2,2-trifluoroethyl group, 2,2,2-trifluoroethyl group, 1,1,2,2-tetrafluoroethyl group, 1,1,2,2,2-pentafluoroethyl group 1-fluoropropyl group, 2-fluoropropyl group, 3-fluoropropyl group, 1,1-difluoropropyl group, 2,2-difluoropropyl group, 3,3-difluoropropylene Group, 2,3,3-trifluoropropyl group, 3,3,3-trifluoropropyl group, 2,2,3,3-tetrafluoropropyl group, 2,2,3,3,3-pentafluoropropyl Group, 1,1,2,3,3,3-hexafluoropropyl group, 1,1,2,2,3,3,3-heptafluoropropyl group, 1,1-bis (trifluoromethyl) methyl group Perfluoroisopropyl group, 2,3,3,3-tetrafluoro-2- (trifluoromethyl) propyl group, 4-fluorobutyl group, 2-fluorobutyl group, 2,2-difluorobutyl group, 3-fluoro Butyl group, 3,3-difluorobutyl group, 4,4-difluorobutyl group, 4,4,4-trifluorobutyl group, 2,2,3-trifluorobutyl group, 2,2,3,3-tetra Fluorobutyl 2,2,3,4-tetrafluorobutyl group, 3,3,4,4-tetrafluorobutyl group, 2,2,3,4,4-pentafluorobutyl group, 2,2,3,4, 4,4-hexafluorobutyl group, 2,2,3,3,4,4-hexafluorobutyl group, 2,2,3,3,4,4,4-heptafluorobutyl group, 1,1,2 2,3,3,4,4-octafluorobutyl group, 1- (trimethylsilyl) methyl group and 2- (trimethylsilyl) ethyl group.

  In the present active compound, examples of the “C3-C6 alkenyl group substituted with one or more groups selected from group A” include, for example, 3,3-dichloro-2-propenyl group, 2,3,3-trichloro-2- Propenyl, 3,3-difluoro-2-propenyl, 2,3-difluoro-2-propenyl, 4,4,4-trifluoro-2-butenyl and 2,3,4,4,4-penta A fluoro-2-butenyl group may be mentioned.

As an aspect of this active compound used for this invention, the following are mentioned, for example.
A pyrimidine compound represented by formula (1), wherein Q is oxygen;
A pyrimidine compound represented by formula (1), wherein Q is sulfur;
A pyrimidine compound represented by formula (1), wherein R ¹ is hydrogen;
A pyrimidine compound represented by formula (1), wherein R ¹ is an amino group;

A pyrimidine compound represented by formula (1), wherein R ² is hydrogen, a halogen, a nitro group, an amino group, a cyano group, or a C1-C6 chain hydrocarbon group optionally substituted with a halogen;
A pyrimidine compound represented by formula (1), wherein R ² is hydrogen, halogen, or a C1-C6 chain hydrocarbon group optionally substituted with halogen;
A pyrimidine compound represented by formula (1), wherein R ² is hydrogen, halogen, or a C1-C6 alkyl group optionally substituted with halogen;
A pyrimidine compound represented by formula (1), wherein R ² is hydrogen, halogen or a C1-C6 alkyl group;
A pyrimidine compound represented by formula (1), wherein R ² is hydrogen, fluorine, chlorine, bromine or a C1-C6 alkyl group;
A pyrimidine compound represented by formula (1), wherein R ² is hydrogen, fluorine, chlorine, bromine or a methyl group;

A pyrimidine compound represented by formula (1), wherein Q is oxygen, and R ³ is a C1-C6 alkyl group substituted with one or more groups selected from Group A;
A pyrimidine compound represented by formula (1), wherein Q is oxygen, and R ³ is a C3-C6 alkenyl group substituted with one or more groups selected from Group A;
A pyrimidine compound represented by formula (1), wherein Q is oxygen and R ³ is a C1-C6 alkyl group substituted with a trimethylsilyl group;
A pyrimidine compound represented by formula (1), wherein Q is oxygen and R ³ is a C1-C6 alkyl group substituted with halogen or a C3-C6 alkenyl group substituted with halogen;
A pyrimidine compound represented by formula (1), wherein Q is oxygen and R ³ is a C1-C6 alkyl group substituted with halogen;
A pyrimidine compound represented by formula (1), wherein Q is oxygen and R ³ is a C3-C6 alkenyl group substituted with halogen;
A pyrimidine compound represented by formula (1), wherein Q is oxygen, and R ³ is a C1-C6 alkyl group substituted with 1 to 8 fluorine or chlorine;
A pyrimidine compound represented by formula (1), wherein Q is oxygen and R ³ is a C1-C6 alkyl group substituted with 1 to 8 fluorines;
A pyrimidine compound represented by formula (1), wherein Q is oxygen and R ³ is a C1-C6 alkyl group substituted with 1 to 8 chlorines;
In the formula (1), Q is oxygen, R ³ is 2,2-dichloropropyl group, 2-chloro-2-methylpropyl group, 2,2,2-trichloroethyl group, 1-methyl-2,2 , 2-trichloroethyl group, 2,2,3,3-tetrafluoropropyl group, 2,2,3,3,3-pentafluoropropyl group, 1,1-bis (trifluoromethyl) methyl group, perfluoro Isopropyl group, 4,4,4-trifluorobutyl group, 2,2,3,3,4,4,4-heptafluorobutyl group, 2,2,3,4,4,4-hexafluorobutyl group, 2,2,3,3,4,4-hexafluorobutyl group, 2,2-bis (trifluoromethyl) propyl group, 2-methyl-2- (trifluoromethyl) propyl group, or 2,2,3 , 3,4,4,5,5-octafluo Pyrimidine compound pentyl group;

A pyrimidine compound represented by formula (1), wherein Q is oxygen, R ² is hydrogen, halogen or a C1-C6 alkyl group optionally substituted with halogen, and R ¹ is hydrogen;
In Formula (1), Q is oxygen, R ² is a C1-C6 alkyl group optionally substituted with hydrogen, halogen, or halogen, R ¹ is hydrogen, and R ³ is substituted with halogen. A pyrimidine compound which is a C1-C6 alkyl group or a C3-C6 alkenyl group substituted with a halogen;
A pyrimidine in which Q is oxygen, R ² is hydrogen, halogen or a C1-C6 alkyl group, R ¹ is hydrogen, and R ³ is a C1-C6 alkyl group substituted by halogen in formula (1) Compound;
In formula (1), Q is oxygen, G ¹ is nitrogen, R ² is hydrogen, halogen or a C1-C6 alkyl group optionally substituted with halogen, R ¹ is hydrogen, R ^{1 A} pyrimidine compound wherein ³ is a C1-C6 alkyl group substituted with halogen;
In Formula (1), Q is oxygen, R ² is a C1-C6 alkyl group optionally substituted with hydrogen, halogen, or halogen, R ¹ is hydrogen, and R ³ is substituted with halogen. A pyrimidine compound which is a C1-C6 alkyl group;
In the formula (1), Q is oxygen, R ² is hydrogen, halogen or a C1-C6 alkyl group optionally substituted with halogen, R ¹ is hydrogen, and R ³ is 1 to 8 A pyrimidine compound which is a C1-C6 alkyl group substituted with fluorine or chlorine
In the formula (1), Q is oxygen, R ² is hydrogen, halogen or a C1-C6 alkyl group optionally substituted with halogen, R ¹ is hydrogen, and R ³ is 1 to 8 A pyrimidine compound which is a C1-C6 alkyl group substituted with fluorine or chlorine

〔式中、
Ｒ^2Aは水素、Ｃ１−Ｃ３アルキル又はハロゲンを表し、
Ｒ^3Aはハロゲンで置換されていてもよいＣ１−Ｃ６アルキル基又はハロゲンで置換されていてもよいＣ３−Ｃ６アルケニル基を表す。〕
で示されるピリミジン化合物。 In the formula (1), Q is oxygen, G ¹ is nitrogen, R ¹ is hydrogen, R ² is hydrogen, C1-C3 alkyl or halogen, and R ³ is substituted with halogen. A pyrimidine compound which is a good C1-C6 alkyl group or a C3-C6 alkenyl group optionally substituted by halogen; ie, formula (A)

[Where,
R ^2A represents hydrogen, C1-C3 alkyl or halogen;
R ^3A represents a C1-C6 alkyl group which may be substituted with halogen or a C3-C6 alkenyl group which may be substituted with halogen. ]
The pyrimidine compound shown by these.

As an aspect of this invention composition, the following are mentioned, for example.
A composition comprising a pyrimidine compound represented by the formula (A) and the present organophosphorus compound;
A composition containing a pyrimidine compound represented by the formula (A) and chlorpyrifos;
A composition containing the pyrimidine compound represented by the formula (A) and the present organophosphorus compound in a weight ratio of the pyrimidine compound represented by the formula (A) / the present organophosphorus compound = 5: 95 to 95: 5;
A composition comprising a pyrimidine compound represented by formula (A) and chlorpyrifos in a weight ratio of pyrimidine compound represented by formula (A) / chlorpyrifos = 5: 95 to 95: 5.

Next, the manufacturing method of this active compound which is an active ingredient in this invention composition is demonstrated.
The active compound can be produced, for example, according to the following (Production Method A) to (Production Method D).

〔式中、Ｒ¹、Ｒ²およびＧ¹は、前記と同じ意味を表す。〕
で示される化合物（以下、化合物（２）と記す。）と、
式（３）

〔式中、Ｒ³およびＱは、前記と同じ意味を表す。〕
で示される化合物（以下、化合物（３）と記す。）とを反応させることにより製造することができる。
該反応は、溶媒の存在下または非存在下で行われる。反応に用いられる溶媒としては、例えば水、１，４−ジオキサン、ジエチルエーテル、テトラヒドロフラン、tert−ブチルメチルエーテル等のエーテル、ジクロロメタン、クロロホルム、四塩化炭素、１，２−ジクロロエタン、クロロベンゼン等のハロゲン化炭化水素、トルエン、ベンゼン、キシレン等の炭化水素、アセトニトリル等のニトリル、Ｎ，Ｎ−ジメチルホルムアミド、Ｎ−メチルピロリドン（以下、ＮＭＰと記す。）、１，３−ジメチル−２−イミダゾリジノン、ジメチルスルホキシド等の非プロトン性極性溶媒およびこれらの混合物が挙げられる。
該反応に用いられる化合物（３）の量は、化合物（２）１モルに対して、通常１〜２モルの割合である。
該反応は、通常、塩基の存在下で行われる。塩基の存在下で行われる場合に用いられる塩基としては、例えばピリジン、ピコリン、２，６−ルチジン、１，８−ジアザビシクロ〔５，４，０〕７−ウンデセン（以下、ＤＢＵと記す。）、１，５−ジアザビシクロ〔４，３，０〕５−ノネン等の含窒素複素環化合物、トリエチルアミン、Ｎ−エチルジイソプロピルアミン等の第３級アミン、炭酸カリウム、水素化ナトリウム等の無機塩基が挙げられる。
塩基の存在下で行われる場合に用いられる塩基の量は、化合物（２）１モルに対して、通常１モル以上である。
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、反応混合物を水に注加した後、有機溶媒抽出する、または、析出した沈殿を濾取することにより本活性化合物を単離することができる。単離された本活性化合物は、再結晶、クロマトグラフィー等により更に精製することもできる。 (Production method A)
The active compound is
Formula (2)

[Wherein R ¹ , R ² and G ¹ represent the same meaning as described above. ]
A compound represented by the following (hereinafter referred to as compound (2));
Formula (3)

[Wherein R ³ and Q represent the same meaning as described above. ]
It can manufacture by making the compound shown below (it is hereafter described as a compound (3)) react.
The reaction is performed in the presence or absence of a solvent. Examples of the solvent used in the reaction include water, ethers such as 1,4-dioxane, diethyl ether, tetrahydrofuran, and tert-butyl methyl ether, and halogenations such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, and chlorobenzene. Hydrocarbons, hydrocarbons such as toluene, benzene, xylene, nitriles such as acetonitrile, N, N-dimethylformamide, N-methylpyrrolidone (hereinafter referred to as NMP), 1,3-dimethyl-2-imidazolidinone, Examples include aprotic polar solvents such as dimethyl sulfoxide and mixtures thereof.
The amount of compound (3) used in the reaction is usually 1 to 2 moles relative to 1 mole of compound (2).
The reaction is usually performed in the presence of a base. Examples of the base used when the reaction is performed in the presence of a base include pyridine, picoline, 2,6-lutidine, 1,8-diazabicyclo [5,4,0] 7-undecene (hereinafter referred to as DBU), and the like. Examples include nitrogen-containing heterocyclic compounds such as 1,5-diazabicyclo [4,3,0] 5-nonene, tertiary amines such as triethylamine and N-ethyldiisopropylamine, and inorganic bases such as potassium carbonate and sodium hydride. .
When performed in the presence of a base, the amount of the base used is usually 1 mol or more per 1 mol of the compound (2).
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 active compound can be isolated by pouring the reaction mixture into water and extracting the mixture with an organic solvent, or collecting a deposited precipitate by filtration. The isolated active compound can be further purified by recrystallization, chromatography or the like.

〔式中、Ｒ²、Ｒ³、ＱおよびＧ¹は、前記と同じ意味を表す。〕
で示される化合物（以下、本活性化合物（１−ｉ）と記す。）は、
式（４）

〔式中、Ｒ²およびＲ³は前記と同じ意味を表す。〕
で示される化合物（以下、化合物（４）と記す。）と、
式（５）

〔式中、Ｇ¹は前記と同じ意味を表す。〕
で示される化合物（以下、化合物（５）と記す。）とを反応させることにより製造することができる。
該反応は、溶媒の存在下または非存在下で行われる。反応に用いられる溶媒としては、例えば水、１，４−ジオキサン、ジエチルエーテル、テトラヒドロフラン、tert−ブチルメチルエーテル等のエーテル、ジクロロメタン、クロロホルム、四塩化炭素、１，２−ジクロロエタン、クロロベンゼン等のハロゲン化炭化水素、トルエン、ベンゼン、キシレン等の炭化水素、アセトニトリル等のニトリル、Ｎ，Ｎ−ジメチルホルムアミド、ＮＭＰ、１，３−ジメチル−２−イミダゾリジノン、ジメチルスルホキシド等の非プロトン性極性溶媒およびこれらの混合物が挙げられる。
該反応に用いられる化合物（５）の量は、化合物（４）１モルに対して、通常１〜２モルの割合である。
該反応は、通常、塩基の存在下で行われる。塩基の存在下で行われる場合に用いられる塩基としては、例えばピリジン、ピコリン、２，６−ルチジン、ＤＢＵ、１，５−ジアザビシクロ〔４，３，０〕５−ノネン等の含窒素複素環化合物、トリエチルアミン、Ｎ−エチルジイソプロピルアミン等の第３級アミン、炭酸カリウム、水素化ナトリウム等の無機塩基が挙げられる。
塩基の存在下で行われる場合に用いられる塩基の量は、化合物（４）１モルに対して、通常１モル以上である。
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、反応混合物を水に注加した後、有機溶媒抽出する、または、析出した沈殿を濾取することにより本活性化合物（１−ｉ）を単離することができる。単離された本活性化合物（１−ｉ）は、再結晶、クロマトグラフィー等により更に精製することもできる。 (Production method B)
Among the active compounds,
Formula (1-i)

[Wherein R ² , R ³ , Q and G ¹ represent the same meaning as described above. ]
(Hereinafter referred to as the present active compound (1-i))
Formula (4)

[Wherein R ² and R ³ represent the same meaning as described above. ]
A compound represented by formula (hereinafter referred to as compound (4)),
Formula (5)

[Wherein G ¹ represents the same meaning as described above. ]
It can manufacture by making the compound (henceforth a compound (5)) shown by reacting.
The reaction is performed in the presence or absence of a solvent. Examples of the solvent used in the reaction include water, ethers such as 1,4-dioxane, diethyl ether, tetrahydrofuran, and tert-butyl methyl ether, and halogenations such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, and chlorobenzene. Hydrocarbons such as hydrocarbons, toluene, benzene, xylene, nitriles such as acetonitrile, aprotic polar solvents such as N, N-dimethylformamide, NMP, 1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide and the like Of the mixture.
The amount of the compound (5) used in the reaction is usually 1 to 2 moles relative to 1 mole of the compound (4).
The reaction is usually performed in the presence of a base. Examples of the base used in the presence of a base include nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2,6-lutidine, DBU, and 1,5-diazabicyclo [4,3,0] 5-nonene. And tertiary amines such as triethylamine and N-ethyldiisopropylamine, and inorganic bases such as potassium carbonate and sodium hydride.
The amount of the base used when the reaction is performed in the presence of a base is usually 1 mol or more per 1 mol of the compound (4).
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 active compound (1-i) can be isolated by pouring the reaction mixture into water and extracting the mixture with an organic solvent, or collecting a deposited precipitate by filtration. The isolated active compound (1-i) can be further purified by recrystallization, chromatography or the like.

〔式中、Ｒ¹、Ｒ²およびＧ¹は前記と同じ意味を表す。〕
で示される化合物（以下、化合物（６）と記す。）と、
化合物（３）とを反応させることにより製造することができる。
該反応は、溶媒の存在下または非存在下で行われる。反応に用いられる溶媒としては、例えば水、１，４−ジオキサン、ジエチルエーテル、テトラヒドロフラン、tert−ブチルメチルエーテル等のエーテル、ジクロロメタン、クロロホルム、四塩化炭素、１，２−ジクロロエタン、クロロベンゼン等のハロゲン化炭化水素、トルエン、ベンゼン、キシレン等の炭化水素、アセトニトリル等のニトリル、Ｎ，Ｎ−ジメチルホルムアミド、ＮＭＰ、１，３−ジメチル−２−イミダゾリジノン、ジメチルスルホキシド等の非プロトン性極性溶媒およびこれらの混合物が挙げられる。
該反応に用いられる化合物（３）の量は、化合物（６）１モルに対して、通常１〜２モルの割合である。
該反応は、通常、塩基の存在下で行われる。塩基の存在下で行われる場合に用いられる塩基としては、例えばピリジン、ピコリン、２，６−ルチジン、ＤＢＵ、１，５−ジアザビシクロ〔４，３，０〕５−ノネン等の含窒素複素環化合物、トリエチルアミン、Ｎ−エチルジイソプロピルアミン等の第３級アミン、炭酸カリウム、水素化ナトリウム等の無機塩基が挙げられる。
塩基の存在下で行われる場合に用いられる塩基の量は、化合物（６）１モルに対して、通常１モル以上である。
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、反応混合物を水に注加した後、有機溶媒抽出する、または、析出した沈殿を濾取することにより本活性化合物を単離することができる。単離された本活性化合物は、再結晶、クロマトグラフィー等により更に精製することもできる。 (Production method C)
The active compound is
Formula (6)

[Wherein, R ¹ , R ² and G ¹ represent the same meaning as described above. ]
A compound represented by formula (hereinafter referred to as compound (6)),
It can be produced by reacting compound (3).
The reaction is performed in the presence or absence of a solvent. Examples of the solvent used in the reaction include water, ethers such as 1,4-dioxane, diethyl ether, tetrahydrofuran, and tert-butyl methyl ether, and halogenations such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, and chlorobenzene. Hydrocarbons such as hydrocarbons, toluene, benzene, xylene, nitriles such as acetonitrile, aprotic polar solvents such as N, N-dimethylformamide, NMP, 1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide and the like Of the mixture.
The amount of compound (3) used in the reaction is usually 1 to 2 moles relative to 1 mole of compound (6).
The reaction is usually performed in the presence of a base. Examples of the base used in the presence of a base include nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2,6-lutidine, DBU, and 1,5-diazabicyclo [4,3,0] 5-nonene. And tertiary amines such as triethylamine and N-ethyldiisopropylamine, and inorganic bases such as potassium carbonate and sodium hydride.
When performed in the presence of a base, the amount of the base used is usually 1 mol or more per 1 mol of the compound (6).
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 active compound can be isolated by pouring the reaction mixture into water and extracting the mixture with an organic solvent, or collecting a deposited precipitate by filtration. The isolated active compound can be further purified by recrystallization, chromatography or the like.

〔式中、Ｒ¹、Ｒ²、Ｇ¹およびＱは前記と同じ意味を表す。〕
で示される化合物（以下、化合物（７）と記す。）と、
式（８）

〔式中、Ｒ³は前記と同じ意味を表し、Ｌは塩素、臭素、ヨウ素、パラトルエンスルホニルオキシ基またはメタンスルホニルオキシ基等の脱離基を表す。〕
で示される化合物（以下、化合物（８）と記す。）とを反応させることにより製造することができる。
該反応は、溶媒の存在下または非存在下で行われる。反応に用いられる溶媒としては、例えば水、１，４−ジオキサン、ジエチルエーテル、テトラヒドロフラン、tert−ブチルメチルエーテル等のエーテル、ジクロロメタン、クロロホルム、四塩化炭素、１，２−ジクロロエタン、クロロベンゼン等のハロゲン化炭化水素、トルエン、ベンゼン、キシレン等の炭化水素、アセトニトリル等のニトリル、Ｎ，Ｎ−ジメチルホルムアミド、ＮＭＰ、１，３−ジメチル−２−イミダゾリジノン、ジメチルスルホキシド等の非プロトン性極性溶媒およびこれらの混合物が挙げられる。
該反応に用いられる化合物（８）の量は、化合物（７）１モルに対して、通常１〜２モルの割合である。
該反応は、通常、塩基の存在下で行われる。塩基の存在下で行われる場合に用いられる塩基としては、例えばピリジン、ピコリン、２，６−ルチジン、ＤＢＵ、１，５−ジアザビシクロ〔４，３，０〕５−ノネン等の含窒素複素環化合物、トリエチルアミン、Ｎ−エチルジイソプロピルアミン等の第３級アミン、炭酸カリウム、水素化ナトリウム等の無機塩基が挙げられる。
塩基の存在下で行われる場合に用いられる塩基の量は、化合物（７）１モルに対して、通常１モル以上である。
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、反応混合物を水に注加した後、有機溶媒抽出する、または、析出した沈殿を濾取することにより本活性化合物を単離することができる。単離された本活性化合物は、再結晶、クロマトグラフィー等により更に精製することもできる。 (Production Method D)
The active compound is
Formula (7)

[Wherein R ¹ , R ² , G ¹ and Q represent the same meaning as described above. ]
(Hereinafter referred to as compound (7)),
Formula (8)

[Wherein, R ³ represents the same meaning as described above, and L represents a leaving group such as chlorine, bromine, iodine, para-toluenesulfonyloxy group or methanesulfonyloxy group. ]
It can manufacture by making the compound (henceforth a compound (8)) shown by reacting.
The reaction is performed in the presence or absence of a solvent. Examples of the solvent used in the reaction include water, ethers such as 1,4-dioxane, diethyl ether, tetrahydrofuran, and tert-butyl methyl ether, and halogenations such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, and chlorobenzene. Hydrocarbons such as hydrocarbons, toluene, benzene, xylene, nitriles such as acetonitrile, aprotic polar solvents such as N, N-dimethylformamide, NMP, 1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide and the like Of the mixture.
The amount of compound (8) used in the reaction is usually 1 to 2 moles relative to 1 mole of compound (7).
The reaction is usually performed in the presence of a base. Examples of the base used in the presence of a base include nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2,6-lutidine, DBU, and 1,5-diazabicyclo [4,3,0] 5-nonene. And tertiary amines such as triethylamine and N-ethyldiisopropylamine, and inorganic bases such as potassium carbonate and sodium hydride.
The amount of the base used when the reaction is carried out in the presence of a base is usually 1 mol or more per 1 mol of the compound (7).
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 active compound can be isolated by pouring the reaction mixture into water and extracting the mixture with an organic solvent, or collecting a deposited precipitate by filtration. The isolated active compound can be further purified by recrystallization, chromatography or the like.

  Next, the manufacturing method of the manufacturing intermediate of this active compound is demonstrated. A part of the production intermediate is a compound that is commercially available or can be produced according to known literature. For example, it can also be produced by the following method.

〔式中、Ｒ²及びＧ¹は、前記と同じ意味を表す。〕
で示される化合物（以下、化合物（２−ｉ）と記す。）は、
式（９）

〔式中、Ｒ²は前記と同じ意味を表す。〕
で示される化合物（以下、化合物（９）と記す。）と、
化合物（５）とを反応させることにより製造することができる。
該反応は、溶媒の存在下または非存在下で行われる。反応に用いられる溶媒としては、例えば水、１，４−ジオキサン、ジエチルエーテル、テトラヒドロフラン、tert−ブチルメチルエーテル等のエーテル、ジクロロメタン、クロロホルム、四塩化炭素、１，２−ジクロロエタン、クロロベンゼン等のハロゲン化炭化水素、トルエン、ベンゼン、キシレン等の炭化水素、アセトニトリル等のニトリル、Ｎ，Ｎ−ジメチルホルムアミド、ＮＭＰ、１，３−ジメチル−２−イミダゾリジノン、ジメチルスルホキシド等の非プロトン性極性溶媒およびこれらの混合物が挙げられる。
該反応に用いられる化合物（５）の量は、化合物（９）１モルに対して、通常１〜２モルの割合である。
該反応は、通常、塩基の存在下で行われる。塩基の存在下で行われる場合に用いられる塩基としては、例えばピリジン、ピコリン、２，６−ルチジン、ＤＢＵ、１，５−ジアザビシクロ〔４，３，０〕５−ノネン等の含窒素複素環化合物、トリエチルアミン、Ｎ−エチルジイソプロピルアミン等の第３級アミン、炭酸カリウム、水素化ナトリウム等の無機塩基が挙げられる。
塩基の存在下で行われる場合に用いられる塩基の量は、化合物（９）１モルに対して、通常１モル以上である。
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、反応混合物を水に注加した後、有機溶媒抽出する、または、析出した沈殿を濾取することにより化合物（２−ｉ）を単離することができる。単離された化合物（２−ｉ）は、再結晶、クロマトグラフィー等により更に精製することもできる。 (Reference production method 1)
Of the compounds (2)
Formula (2-i)

[Wherein R ² and G ¹ represent the same meaning as described above. ]
(Hereinafter referred to as compound (2-i))
Formula (9)

[Wherein R ² represents the same meaning as described above. ]
A compound represented by formula (hereinafter referred to as compound (9)),
It can be produced by reacting with compound (5).
The reaction is performed in the presence or absence of a solvent. Examples of the solvent used in the reaction include water, ethers such as 1,4-dioxane, diethyl ether, tetrahydrofuran, and tert-butyl methyl ether, and halogenations such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, and chlorobenzene. Hydrocarbons such as hydrocarbons, toluene, benzene, xylene, nitriles such as acetonitrile, aprotic polar solvents such as N, N-dimethylformamide, NMP, 1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide and the like Of the mixture.
The amount of the compound (5) used in the reaction is usually 1 to 2 mol relative to 1 mol of the compound (9).
The reaction is usually performed in the presence of a base. Examples of the base used in the presence of a base include nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2,6-lutidine, DBU, and 1,5-diazabicyclo [4,3,0] 5-nonene. And tertiary amines such as triethylamine and N-ethyldiisopropylamine, and inorganic bases such as potassium carbonate and sodium hydride.
When performed in the presence of a base, the amount of the base used is usually 1 mol or more per 1 mol of the compound (9).
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 (2-i) can be isolated by pouring the reaction mixture into water and extracting the mixture with an organic solvent, or collecting a deposited precipitate by filtration. The isolated compound (2-i) can be further purified by recrystallization, chromatography or the like.

〔式中、Ｒ²は前記と同じ意味を表す。〕
で示される化合物（以下、化合物（２−ｉｉ）と記す。）は、
式（１０）

〔式中、Ｒ²は前記と同じ意味を表す。〕
で示される化合物（以下、化合物（１０）と記す。）と、
式（１１）

〔式中、Ｒ⁵は、ハロゲンで置換されていてもよいＣ１−Ｃ６アルキル基を表す。〕
で示される化合物（以下、化合物（１１）と記す。）とを反応させることにより製造することができる。
該反応は、溶媒の存在下または非存在下で行われる。反応に用いられる溶媒としては、例えば水；１，４−ジオキサン、ジエチルエーテル、テトラヒドロフラン、tert−ブチルメチルエーテル等のエーテル；ジクロロメタン、クロロホルム、四塩化炭素、１，２−ジクロロエタン、クロロベンゼン等のハロゲン化炭化水素；トルエン、ベンゼン、キシレン等の炭化水素；アセトニトリル等のニトリル；Ｎ，Ｎ−ジメチルホルムアミド、ＮＭＰ、１，３−ジメチル−２−イミダゾリジノン、ジメチルスルホキシド等の非プロトン性極性化合物；およびこれらの混合物が挙げられる。
該反応に用いられる化合物（１１）の量は、化合物（１０）１モルに対して、通常１〜２モルである。
該反応の反応温度は、通常、−２０〜１００℃の範囲である。該反応の反応時間は、通常、０．１〜２４時間の範囲である。
反応終了後は、反応混合物を水に注加してから有機溶媒抽出し、有機層を濃縮することにより化合物（２−ｉｉ）を単離することができる。単離された化合物（２−ｉｉ）は、クロマトグラフィー、蒸留等により更に精製することもできる。 (Reference production method 2)
Of the compounds (2)
Formula (2-ii)

[Wherein R ² represents the same meaning as described above. ]
(Hereinafter referred to as the compound (2-ii))
Formula (10)

[Wherein R ² represents the same meaning as described above. ]
A compound represented by formula (hereinafter referred to as compound (10)),
Formula (11)

[Wherein, R ⁵ represents a C1-C6 alkyl group which may be substituted with halogen. ]
It can manufacture by making the compound shown below (it is hereafter described as a compound (11)) react.
The reaction is performed in the presence or absence of a solvent. Examples of the solvent used in the reaction include water; ethers such as 1,4-dioxane, diethyl ether, tetrahydrofuran, and tert-butyl methyl ether; halogenation such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, and chlorobenzene. Hydrocarbons such as toluene, benzene, xylene; nitriles such as acetonitrile; aprotic polar compounds such as N, N-dimethylformamide, NMP, 1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide; and These mixtures are mentioned.
The amount of compound (11) used in the reaction is usually 1 to 2 moles relative to 1 mole of compound (10).
The reaction temperature of the reaction is usually in the range of -20 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (2-ii) can be isolated by pouring the reaction mixture into water and extracting the mixture with an organic solvent, and concentrating the organic layer. The isolated compound (2-ii) can be further purified by chromatography, distillation or the like.

(Reference production method 3)
Compound (10) can be produced by reacting compound (9) with hydrazine.
The reaction is performed in the presence or absence of a solvent. Examples of the solvent used in the reaction include water; ethers such as 1,4-dioxane, diethyl ether, tetrahydrofuran, and tert-butyl methyl ether; halogenation such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, and chlorobenzene. Hydrocarbons such as toluene, benzene, xylene; nitriles such as acetonitrile; aprotic polar compounds such as N, N-dimethylformamide, NMP, 1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide; and These mixtures are mentioned.
Examples of hydrazine used in the reaction include hydrazine and hydrazine hydrate.
The amount of hydrazine used in the reaction is usually 1 to 10 mol per 1 mol of compound (9).
The reaction is usually performed in the presence of a base. Examples of the base used in the reaction include nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2,6-lutidine, DBU, 1,5-diazabicyclo [4,3,0] 5-nonene; triethylamine, N-ethyl Tertiary amines such as diisopropylamine; and inorganic bases such as potassium carbonate and sodium hydride.
The amount of the base used in the reaction is usually 1 mol or more per 1 mol of the compound (9).
The reaction temperature of the reaction is usually in the range of 0 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the reaction mixture is poured into water and then extracted with an organic solvent, and the organic layer is concentrated; the reaction mixture is poured into water and the resulting solid is collected by filtration; or formed in the reaction mixture The collected solid can be collected by filtration to isolate compound (10). The isolated compound (10) can be further purified by recrystallization, chromatography or the like.

(Reference production method 4)
Compound (4) can be produced by reacting compound (9) with compound (3).
The reaction is performed in the presence or absence of a solvent. Examples of the solvent used in the reaction include water, ethers such as 1,4-dioxane, diethyl ether, tetrahydrofuran, and tert-butyl methyl ether, and halogenations such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, and chlorobenzene. Hydrocarbons such as hydrocarbons, toluene, benzene, xylene, nitriles such as acetonitrile, aprotic polar solvents such as N, N-dimethylformamide, NMP, 1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide and the like Of the mixture.
The amount of the compound (3) used in the reaction is usually 1 to 2 moles relative to 1 mole of the compound (9).
The reaction is usually performed in the presence of a base. Examples of the base used in the presence of a base include nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2,6-lutidine, DBU, and 1,5-diazabicyclo [4,3,0] 5-nonene. And tertiary amines such as triethylamine and N-ethyldiisopropylamine, and inorganic bases such as potassium carbonate and sodium hydride. When performed in the presence of a base, the amount of the base used is usually 1 mol or more per 1 mol of the compound (9).
The reaction temperature of the reaction is usually in the range of 0 to 100 ° C., and the reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (4) can be isolated by pouring the reaction mixture into water and extracting the mixture with an organic solvent. The isolated compound (4) can be further purified by chromatography or the like.

〔式中、Ｒ²及びＧ¹は前記と同じ意味を表す。〕
で示される化合物（以下、化合物（６−ｉ）と記す。）は、化合物（９）と化合物（５）とを反応させることにより製造することができる。
該反応は、溶媒の存在下または非存在下で行われる。反応に用いられる溶媒としては、例えば水、１，４−ジオキサン、ジエチルエーテル、テトラヒドロフラン、tert−ブチルメチルエーテル等のエーテル、ジクロロメタン、クロロホルム、四塩化炭素、１，２−ジクロロエタン、クロロベンゼン等のハロゲン化炭化水素、トルエン、ベンゼン、キシレン等の炭化水素、アセトニトリル等のニトリル、Ｎ，Ｎ−ジメチルホルムアミド、ＮＭＰ、１，３−ジメチル−２−イミダゾリジノン、ジメチルスルホキシド等の非プロトン性極性溶媒およびこれらの混合物が挙げられる。
該反応に用いられる化合物（５）の量は、化合物（９）１モルに対して、通常２〜３モルの割合である。
該反応は、通常、塩基の存在下で行われる。塩基の存在下で行われる場合に用いられる塩基としては、例えばピリジン、ピコリン、２，６−ルチジン、ＤＢＵ、１，５−ジアザビシクロ〔４，３，０〕５−ノネン等の含窒素複素環化合物、トリエチルアミン、Ｎ−エチルジイソプロピルアミン等の第３級アミン、炭酸カリウム、水素化ナトリウム等の無機塩基が挙げられる。塩基の存在下で行われる場合に用いられる塩基の量は、化合物（９）１モルに対して、通常２モル以上である。
該反応の反応温度は、通常、０〜１００℃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、反応混合物を水に注加した後、有機溶媒抽出する、または、析出した沈殿を濾取することにより化合物（６−ｉ）を単離することができる。単離された化合物（６−ｉ）は、再結晶、クロマトグラフィー等により更に精製することもできる。 (Reference production method 5)
Of the compounds (6), the formula (6-i)

[Wherein R ² and G ¹ represent the same meaning as described above. ]
(Hereinafter referred to as compound (6-i)) can be produced by reacting compound (9) with compound (5).
The reaction is performed in the presence or absence of a solvent. Examples of the solvent used in the reaction include water, ethers such as 1,4-dioxane, diethyl ether, tetrahydrofuran, and tert-butyl methyl ether, and halogenations such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, and chlorobenzene. Hydrocarbons such as hydrocarbons, toluene, benzene, xylene, nitriles such as acetonitrile, aprotic polar solvents such as N, N-dimethylformamide, NMP, 1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide and the like Of the mixture.
The amount of the compound (5) used in the reaction is usually 2 to 3 moles relative to 1 mole of the compound (9).
The reaction is usually performed in the presence of a base. Examples of the base used in the presence of a base include nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2,6-lutidine, DBU, and 1,5-diazabicyclo [4,3,0] 5-nonene. And tertiary amines such as triethylamine and N-ethyldiisopropylamine, and inorganic bases such as potassium carbonate and sodium hydride. The amount of the base used when the reaction is carried out in the presence of a base is usually 2 mol or more per 1 mol of the compound (9).
The reaction temperature of the reaction is usually in the range of 0 to 100 ° C., and the reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (6-i) can be isolated by pouring the reaction mixture into water and extracting the mixture with an organic solvent, or collecting a deposited precipitate by filtration. The isolated compound (6-i) can be further purified by recrystallization, chromatography or the like.

〔式中、Ｒ¹、Ｒ²およびＧ¹は前記と同じ意味を表す。〕
で示される化合物（以下、化合物（７−ｉ）と記す。）は、化合物（６）を加水分解反応に付すことで製造することができる。
該反応は、水の存在下において、塩基あるいは酸の存在下で行われる。必要に応じて、用いられる溶媒としては、例えば１，４−ジオキサン、ジエチルエーテル、テトラヒドロフラン、tert−ブチルメチルエーテル、ジグライム等のエーテル；トルエン、ベンゼン、キシレン等の炭化水素；及びアセトニトリル等のニトリルが挙げられる。
該反応に用いられる塩基としては、例えば炭酸カリウム、水酸化ナトリウム、水酸化カリウム、水素化ナトリウム等の無機塩基；ピリジン、ピコリン、２，６−ルチジン、ＤＢＵ、１，５−ジアザビシクロ〔４，３，０〕５−ノネン等の含窒素複素環化合物；及びトリエチルアミン、Ｎ−エチルジイソプロピルアミン等の第３級アミンが挙げられる。該反応が塩基の存在下で行われる場合、該反応に用いられる塩基の量は、化合物（６）１モルに対して、通常０．１〜４モルである。
該反応に用いられる酸としては、例えば塩酸、臭酸、硫酸等の無機酸；及び酢酸、パラトルエンスルホン酸等の有機酸が挙げられる。該反応が酸の存在下で行われる場合、該反応に用いられる酸の量は、化合物（６）１モルに対して、通常０．１モル以上である。
該反応の反応温度は、通常、２０〜１２０℃の範囲である。該反応の反応時間は、通常、０．１〜２４時間の範囲である。
反応終了後は、反応混合物を水に注加してから有機溶媒抽出し、有機層を濃縮する；反応混合物を水に注加して生じた固体を濾過により集める；または、反応混合物中に生成した固体を濾過により集めることにより化合物（７−ｉ）を単離することができる。単離された化合物（７−ｉ）は、再結晶、クロマトグラフィー等により更に精製することもできる。 (Reference production method 6)
Of compounds (7)
Formula (7-i)

[Wherein, R ¹ , R ² and G ¹ represent the same meaning as described above. ]
(Hereinafter referred to as compound (7-i)) can be produced by subjecting compound (6) to a hydrolysis reaction.
The reaction is carried out in the presence of water or base or acid. If necessary, examples of the solvent to be used include ethers such as 1,4-dioxane, diethyl ether, tetrahydrofuran, tert-butyl methyl ether and diglyme; hydrocarbons such as toluene, benzene and xylene; and nitriles such as acetonitrile. Can be mentioned.
Examples of the base used in the reaction include inorganic bases such as potassium carbonate, sodium hydroxide, potassium hydroxide and sodium hydride; pyridine, picoline, 2,6-lutidine, DBU, 1,5-diazabicyclo [4,3 , 0] 5-nonene and the like, and tertiary amines such as triethylamine and N-ethyldiisopropylamine. When the reaction is carried out in the presence of a base, the amount of the base used for the reaction is usually 0.1 to 4 mol with respect to 1 mol of compound (6).
Examples of the acid used in the reaction include inorganic acids such as hydrochloric acid, odorous acid, and sulfuric acid; and organic acids such as acetic acid and paratoluenesulfonic acid. When the reaction is carried out in the presence of an acid, the amount of acid used in the reaction is usually 0.1 mol or more per 1 mol of compound (6).
The reaction temperature of the reaction is usually in the range of 20 to 120 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the reaction mixture is poured into water and then extracted with an organic solvent, and the organic layer is concentrated; the reaction mixture is poured into water and the resulting solid is collected by filtration; or formed in the reaction mixture The collected solid is collected by filtration to isolate compound (7-i). The isolated compound (7-i) can be further purified by recrystallization, chromatography or the like.

〔式中、Ｒ¹、Ｒ²およびＧ¹は前記と同じ意味を表す。〕
で示される化合物（以下、化合物（７−ｉｉ）と記す。）は、化合物（７−ｉ）と硫化剤とを反応させることにより製造することができる。
該反応は、溶媒の存在下または非存在下で行われる。反応に用いられる溶媒としては、例えば１，４−ジオキサン、ジエチルエーテル、テトラヒドロフラン、tert−ブチルメチルエーテル、ジグライム等のエーテル、ジクロロメタン、クロロホルム、四塩化炭素、１，２−ジクロロエタン、クロロベンゼン等のハロゲン化炭化水素、トルエン、ベンゼン、キシレン等の炭化水素、アセトニトリル等のニトリル、ピリジン、ピコリン、ルチジン等のピリジンおよびこれらの混合物が挙げられる。
該反応に用いられる硫化剤としては、五硫化ニリン、ローソン試薬（２，４−ビス−（４−メトキシフェニル）−１，３−ジチア−２，４−ジホスフェタン ２，４−ジスルフィド）等が挙げられる。
該反応に用いられる硫化剤の量は、化合物（７−ｉ）1モルに対して、通常１モル以上である。
該反応の反応温度は、通常、０℃〜２００℃の範囲であり、反応時間は、通常、１〜２４時間の範囲である。
反応終了後は、反応混合物中に析出した沈殿を濾取する、または、反応混合物を有機溶媒抽出等により化合物（７−ｉｉ）を単離することができる。単離された化合物（７−ｉｉ）は、再結晶、クロマトグラフィー等によりさらに精製することもできる。 (Reference production method 6)
Of compounds (7)
Formula (7-ii)

[Wherein, R ¹ , R ² and G ¹ represent the same meaning as described above. ]
(Hereinafter referred to as compound (7-ii)) can be produced by reacting compound (7-i) with a sulfurizing agent.
The reaction is performed in the presence or absence of a solvent. Examples of the solvent used in the reaction include ethers such as 1,4-dioxane, diethyl ether, tetrahydrofuran, tert-butyl methyl ether, and diglyme, and halogenations such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, and chlorobenzene. Examples thereof include hydrocarbons, hydrocarbons such as toluene, benzene and xylene, nitriles such as acetonitrile, pyridines such as pyridine, picoline and lutidine, and mixtures thereof.
Examples of the sulfurizing agent used in the reaction include nilin pentasulfide, Lawesson's reagent (2,4-bis- (4-methoxyphenyl) -1,3-dithia-2,4-diphosphetane 2,4-disulfide), and the like. It is done.
The amount of the sulfurizing agent used in the reaction is usually 1 mol or more per 1 mol of the compound (7-i).
The reaction temperature of the reaction is usually in the range of 0 ° C. to 200 ° C., and the reaction time is usually in the range of 1 to 24 hours.
After completion of the reaction, the precipitate precipitated in the reaction mixture can be collected by filtration, or the compound (7-ii) can be isolated from the reaction mixture by organic solvent extraction or the like. The isolated compound (7-ii) can be further purified by recrystallization, chromatography or the like.

  The active compound contained in the composition of the present invention may be one type or two or more types. Preferably they are 1 type or more and 3 types or less.

The organophosphorus compound used in combination with the active compound in the composition of the present invention will be described.
Chlorpyrifos is described in No. 157 of "The Pesticide Manual, Fifteenth Edition" (edited by Clive Tomlin, published by The British Crop Production Council, 2009). ing.
Chlorpyrifosmethyl is described in No. 158 of “The Pesticide Manual, Fifteenth Edition” (edited by Clive Tomlin, published by The British Crop Production Council, 2009). The acephate is listed in No. 3 of “The Pesticide Manual, Fifteenth Edition” (edited by Clive Tomlin, published by The British Crop Production Council, 2009). Are commercially available.
Metamidophos is described in No. 565 of “The Pesticide Manual, Fifteenth Edition” (edited by Clive Tomlin, published by The British Crop Production Council, 2009). Methidathione is described in No. 566 of “The Pesticide Manual, Fifteenth Edition” (edited by Clive Tomlin, published by The British Crop Production Council, 2009). It is commercially available.
Fenitrothion is described in No. 359 of “The Pesticide Manual, Fifteenth Edition” (edited by Clive Tomlin, published by The British Crop Production Council, 2009). The present organic phosphorus compound contained in the composition of the present invention may be one kind or two or more kinds. Preferably they are 1 type or more and 3 types or less.

The active compound and the organophosphorus compound may have geometric isomers and / or stereoisomers, and the present invention includes each of these isomers and mixtures of these isomers.
In addition, the active compound and the organophosphorus compound may form an agrochemically acceptable salt. Examples of such salts include inorganic bases (for example, alkali metals such as sodium, potassium and lithium, alkaline earth metals such as calcium and magnesium, ammonia), and organic bases (for example, pyridine, collidine, triethylamine, triethanol). Amines), inorganic acids (eg hydrochloric acid, hydrobromic acid, hydroiodic acid, phosphoric acid, sulfuric acid, perchloric acid etc.), organic acids (eg formic acid, acetic acid, tartaric acid, malic acid, citric acid, oxalic acid) , Succinic acid, benzoic acid, picric acid, methanesulfonic acid, p-toluenesulfonic acid and the like). In the present invention, the active compound or the organophosphorus compound includes their respective salts.

  In the composition of the present invention, the ratio of the present active compound to the present organophosphorus compound is usually 5:95 to 95: 5, preferably 20:80 to 80 in the weight ratio (= the present active compound: the present organophosphorus compound). : 20 range.

In general, the composition of the present invention contains a carrier to be described later, and is a preparation that can be taken by an agrochemical or animal medicine.
The composition of the present invention comprises dissolving or dispersing the active compound and the organophosphorus compound in a suitable liquid carrier, mixing or adsorbing the active compound and the organophosphorus compound with a suitable solid carrier or ointment base, For example, the following dosage forms can be prepared by a known method such as mixing or dispersing the active compound and the present organophosphorus compound in a suitable gaseous carrier.
The above dosage forms include emulsions, liquids, microemulsions, flowables, oils, wettable powders, granular wettable powders, powders, granules, fine granules, seed coating agents, seed soaking agents, smoke agents, tablets, Microcapsules, sprays, aerosols, carbon dioxide preparations, heat transpiration agents such as mosquito coils, electric mosquito mats, liquid electric mosquito traps, EW agents, ointments, poison baits, capsules, pellets, films, injections, coating agents, Examples include resin preparations and shampoo preparations.
In the preparation, if necessary, auxiliary agents for formulation such as emulsifiers, suspending agents, spreading agents, penetrating agents, wetting agents, thickening agents, stabilizers, fixing agents, binders, dispersing agents, coloring agents and the like. It may be added.

  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 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 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, polyethylene glycol fatty acid ester, and the like, and alkyl sulfonates, alkyl benzene sulfonates, alkyl sulfates, and the like. An ionic 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, polyvinylpyrrolidone, 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).

  In addition to the active compound and the organophosphorus compound, the composition of the present invention comprises an insecticide, acaricide, nematicide, fungicide, plant hormone agent, plant growth regulator, herbicide, synergist or safener An agent may be contained.

The content ratio of the active compound and the organophosphorus compound in the composition of the present invention is usually 0.01 to 95% by weight, preferably about 0.1 to 90% by weight, more preferably, based on the total amount of the composition of the present invention. About 5 to 70% by weight.
Specifically, when the composition of the present invention is in the form of an emulsion, solution, wettable powder, or granular wettable powder, the content is usually about 1 to 90% by weight with respect to the total amount of the composition of the present invention. %, Preferably about 5 to 50% by weight. When the composition of the present invention is in the form of oil or powder, the content is usually about 0.1 to 50% by weight, preferably about 0.1 to 20% by weight. When the composition of the present invention is in the form of granules, the content is usually about 0.1 to 50% by weight, preferably about 0.5 to 20% by weight.
The other pesticidal active ingredient (for example, insecticide, herbicide, acaricide and / or fungicide) blended in the composition of the present invention is preferably about 1 to 80% by weight based on the total amount of the composition of the present invention. More preferably, it is about 1 to 20% by weight.
The content of additives other than the above active ingredients varies depending on the type or content of the pesticidal active ingredient or the dosage form of the preparation, but is usually about 0.001 to 99.9% by weight, preferably about 1 to 99% by weight. is there. For example, the surfactant is usually about 1 to 20% by weight, preferably about 1 to 15% by weight, the flow aid is about 1 to 20% by weight, and the carrier is about 1 to 90% by weight with respect to the total amount of the composition of the present invention. %, Preferably about 1 to 70% by weight can be added. In the case of a liquid preparation, the surfactant is usually added in an amount of about 1 to 20% by weight, preferably about 1 to 10% by weight, and about 20 to 90% by weight of water based on the total amount of the composition of the present invention. . In addition, emulsions, wettable powders, granular wettable powders, and the like can be sprayed by appropriately increasing the dilution with water or the like (for example, about 100 to 5000 times).

  Examples of harmful animals for which the composition of the present invention exhibits a controlling effect include the following harmful arthropods and harmful gastropods.

  Hemiptera: Pepper (Laodelphax striatellus), brown planthopper (Nilaparvata lugens), leafhopper (Sogatella furcifera) and other species, Nephotettix cincticeps, Nephotettip Leafhoppers, cotton aphids (Aphis gossypii), peach aphids (Myzus persicae), radish aphids (Brevicoryne brassicae), snowy aphids (Aphis spiraecola), tulip mustard aphids (Macrosiphum euphorbiae), potato aphids Aphids such as aphids (Rhopalosiphum padi), citrus aphids (Toxoptera citricidus), peach beetles (Hyalopterus pruni), Nezara antennata, hosohelika Riptortus clavetus, Leptocorisa chinensis, Eysarcoris parvus, Halyomorpha mista, Lygus lineolaris, Trichotium esti , Whitefly (Trialeurodes vaporariorum), whitefly (Bemisia tabaci), whitefly (Dialeurodes citri), whitefly (Aleurocanthus spiniferus), whitefly, Aonidiella aurantii, snail Scale (Unaspis citri), Ruby Beetle (Ceroplastes rubens), Icerya purchasi, Fujico scale (Planococcus kraunhiae), Pseudoococcus longispinis, Mi Down mealybugs (Planococus citri), grape mealy bug (Planococcus maritimus), scale insects such as white peach scale (Pseudaulacaspis pentagona), tingidae class, bed bugs such as bed bugs (Cimex lectularius), psyllid, and the like.

  Lepidopterous insects: Chilo suppressalis, Tryporyza incertulas, Cnaphalocrocis medinalis, Notarcha derogata, Plodia interpunctella, Odaltrihis, Ostrinia furnacalis, Ostrinia furnacalis Common moths such as Pediasia teterrellus, Spodoptera litura, Spodoptera exigua, Pseudaletia separata, Mamestra brassicae, Mamestra brassicae, Agrotis ipsila, Agrotis ipsila Heliotis genus, Helicoberpa genus moths, white butterflies (Pieris rapae) squirrels, Adoxofies genus, Grapholita molesta, bean squirrel (Leguminivora glycinivorella), azoxa yam Moth (Matsumuraeses azukivora), apple wolfberry (Adoxophyes orana fasciata), tea wolfberry (Adoxophyes honmai.), Chamonaki (Homona magnanima), midarekamonmon (Archips fuscocupreanus), codling moth (Cydia moth) , Chasohosuga (Caloptilia theivora), Kinsohosoga (Phyllonorycter ringoneella), etc ), Spits such as Pectinophora gossypiella, Potatoes such as Phthhorimaea operculella, Hitritria such as Hyphantria cunea, Hiros such as Tinea translucens, Tineola bisselliella, etc.

  Thrips of the order: Thrips parmi, Scirtothrips dorsalis, Thrips tabaci, and ella F.

  Diptera: Culex pipiens pallens, Culex tritaeniorhynchus, Culex quinquefasciatus, etc., Aedes aegypti, Aedes albopictus, etc. Genus Anopheles, Chironomidae, Musca domestica, Muscina stabulans, and other houseflies, Drosophila, Drosophila, Drosophila, Delia platura, Delia antiqua, Drosophila (Agromyza oryzae), rice leaflet (Hydrellia griseola), tomato leaffly, (Liriomyza sativae), leafworm (Liriomyza trifolii), leafworm (Chromatomyia horticola) and other leafhoppers (Chromatomyia horticola), Flies, fruit flies (Dacus cucurbitae), fruit flies such as Ceratitis capitata, fruit flies, fruit flies such as Megaselia spiracularis trigonus) and other species such as flies and flies.

  Coleoptera: Western corn root worms (Diabrotica virgifera virgifera), Southern corn root worms (Diabrotica undecimpunctata howardi), corn root worms, Anomala cuprea, Anomala rufocuprea, Japanese beetle (Popillia japonica) Moss, maize weevil (Sitophilus zeamais), rice weevil (Lissorhoptrus oryzophilus), weevil (Callosobruchuys chienensis), weevil (Echinocnemus squameus), cotton weevil (Anthonomus grandis), tussophyllum tuss Tenebrio molitor, Tribolium castaneum and other species, Oulema oryzae, Aulacophora femoralis, Phyllotreta striolata, co Leaf beetles such as Leptinotarsa decemlineata, beetles such as Anthrenus verbasci, beetles such as Dermestes maculates, beetles such as tobacco larva (Lasioderma serricorne) Epiracuna, Caterpillars such as Lyctus brunneus, Tomicus piniperda, Nagashimushi, Leopardia, Anoplophora malasiaca, etc. (Paederus fuscipes) etc.

  Pterodoptera: Locusta migratoria, Gryllotalpa africana, Oxya yezoensis, Oxya japonica, crickets, etc.

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

  Lice pests: white lice (Pediculus humanus corporis), white lice (Phthirus pubis), cattle lice (Haematopinus eurysternus), sheep lice (Dalmalinia ovis), pig lice (Haematopinus suis), etc.

  Hymenopteran pests: Monomorium pharaosis, Formica fusca japonica, Ruriari (Ochetellus glaber), Apricot worm (Pristomyrmex pungens), Pheidole noda, Acromyrmex spp., Opis sp (len) Such as ants, hornets, scallops, bees (Athalia rosae), Japanese bees (Athalia japonica), and the like.

Cockroach eye insects: German cockroach (Blattella germanica), Black cockroach (Periplaneta fuliginosa), American cockroach (Periplaneta americana), Great cockroach (Periplaneta brunnea), Great cockroach (Blatta orientalis), etc.
Termite insect pests: Yamato termite (Reticulitermes speratus), termite (Coptotermes formosanus), American white termite (Incisitermes minor), scallop termite (Cryptotermes domesticus), taiwan termite (Odontotermes formosanus), red ant termite (hunsterm termite) Glyptotermes satsumensis, Glyptotermes nakajimai, Caterpillar (Glyptotermes fudamcus), White termite (Glyptotermes kodamai), Ants (Glyptotermes kushimensis), Japanese termites (pants) miyatakei), white termite (Reticulitermes flaviceps amamianus), common termite (Reticulitermes sp.), white termite (Nasutitermes takasagoensis), white termite (Pericapri) termes nitobei), Sinocapritermes mushae, Reticuliterumes flavipes, Reticulitermes hesperus, Reticulitermes virginicus, Reticulitermes tibialis, Heterotermes aureus, Zootermopsis nevadensis and the like.

  Acarid pests: Nite spider mite (Tetranychus urticae), Kanzawa spider mite (Tetranychus kanzawai), Scarlet spider mite (Panonychus citri) Apple spider mite (Panonychus ulmi), Oligonicus spp. Tomato rustic mites (Aculops lycopersici), Chinese radish mites (Calacarus carinatus), Chinese radish mites (Acaphylla theavagrans), Green radish mites (Eriophyes chibaensis), Apple rustic mites (Aculus schlechtendali), mussels photicid mites Scarlet mites (Brevipalpus phoenicis) and other spider mites, mosquito spider mites (Haemaphysalis longicornis), Scarlet tick (Haemaphysalis flava), Dermacentor taiwanicus, Scarlet mite ( Tick such as Ixodes ovatus, Tickling tick (Ixodes persulcatus), Black-legged tick (Ixodes scapularis), Tick (Boophilus microplus), Rhipicephalus sanguineus, Tyrophagus putrescentia, Tyrophagus putrescentia ) And other mites, Dermatophagoides farinae, Dermatophagoides ptrenyssnus, etc. ), Cucumbers such as Ornithonyssus sylvairum, dermatoyssus gallinae, and tsutsugamushi such as Leptotrombidium akamushi. Spiders such as Chiracanthium japonicum and Latrodectus hasseltii.

Lip and limb class: Thereuonema hilgendorfi, Scolopendra subspinipes, etc.
Double-legged class: Japanese red millipede (Oxidus gracilis), Japanese red millipede (Nedyopus tambanus).
Isopods: Armadillidium vulgare, etc.
Gastropods: Limax marginatus, Limax flavus, etc.

The pest control method according to the present invention (hereinafter sometimes referred to as “the present pest control method”) is an effective amount of the active compound and the organophosphorus compound applied to the pest or the habitat of the pest. Apply.
In the present control method, an effective amount of the present active compound and the present organophosphorus compound is applied to a plant, a soil for cultivating a plant, a hydroponics solution, a medium, or the like.
Pests can be controlled by the control method of the present invention.
In the control method of the present invention, the active compound and the organophosphorus compound can be applied as they are without adding any other components, and the active compound and the organophosphorus compound and the insecticide, acaricide, Other chemicals such as nematicides and fungicides may be applied, or the active compound and the organophosphorus compound may be used in combination with natural enemy organisms or natural enemy microorganisms. The active compound and the organophosphorus compound may be applied separately at the same time, but are usually applied as the composition of the present invention from the viewpoint of simplicity during application.
Examples of habitats of harmful animals include plants, paddy fields, dry fields, fields, tea gardens, orchards, non-agricultural lands, houses, seedling trays and seedling boxes, seedling culture soil and seedling mats, hydroponic liquids in hydroponic farms, etc. It is done.
Examples of plants to be applied include foliage, seeds, seed pods, bulbs, and seedlings. Here, the bulb means a bulb, a bulb, a rhizome, a tuber, a tuberous root, and a root support body.
In the control method of the present invention, the active compound and the organophosphorus compound can be applied to harmful animals, harmful animal habitats, etc. by contacting or ingesting the above harmful animals in the same manner as conventional harmful animal control agents. can do.
Examples of such application methods include spraying treatment, soil treatment, seed treatment, and hydroponic liquid treatment.
The above-mentioned spraying treatment, for example, exerts control effects on harmful animals by spraying active ingredients (this active compound and this organophosphorus compound) on the surface of plants such as foliage spraying, trunk spraying, etc. or harmful animals themselves. It is a processing method.
The above-mentioned soil treatment is, for example, a treatment that directly controls harmful animals by giving an active ingredient to the rhizosphere of the plant to be protected, or controls the harmful animals by penetrating and transferring the active ingredients to the inside of the plant. Is the method.
Specifically, the above-mentioned soil treatment includes planting hole treatment, plant source treatment, grooving treatment, rowing treatment, rowing treatment, full surface treatment, side row treatment, water surface treatment, other soil spraying treatment, and other irrigation. Processing, seedling box processing, seedling tray processing, seedbed processing, bed soil mixing processing, and the like can be mentioned.
The seed treatment is, for example, a treatment method that exerts a controlling effect on harmful animals by treating the seed, seed pod or bulb of the plant to be protected directly or in the vicinity thereof with an active ingredient. Specific examples of the seed treatment include spraying, smearing, dipping, impregnation, coating, film coating, and pellet coating.
The above-mentioned hydroponic liquid treatment means, for example, that the plant is harmful by treating the hydroponic liquid etc. with the active ingredient in order to infiltrate and transfer the active ingredient from the root of the plant to be protected to the inside of the plant. This is a treatment method that protects animals from damage. Specific examples of the hydroponic liquid treatment include mixing a hydroponic liquid and mixing a hydroponic liquid.

The pest control method of the present invention can be carried out on agricultural land such as fields, paddy fields, lawns, orchards, or non-agricultural land.
When this active compound and this organophosphorus compound are used for the control of harmful animals in the agricultural field, the dose of this active compound and this organophosphorus compound depends on the type and occurrence of harmful arthropods to be controlled, the formulation Although it can be changed in a wide range according to the form, application time, application place, application method, weather conditions, etc., it is generally 1 to 10,000 g per 10,000 m ² .
Emulsions, wettable powders, flowables and the like are usually diluted with water so that the concentration of the active compound and the organophosphorus compound is 0.01 to 10000 ppm, and granules, powders, etc. are usually Apply as is.

  The active compound, the organophosphorus compound and the water dilution thereof may be sprayed directly on harmful animals or plants, or may be subjected to the soil treatment described above.

  The active compound and the organophosphorus compound can be applied by a method such as wrapping around a plant as a resin preparation processed into a sheet or string, stretching it in the vicinity of the plant, or laying it on the stock soil.

The composition 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.), cucurbits (cucumbers, pumpkins, zucchini, watermelons, melons, etc.), cruciferous 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, apricots, prunes, etc.), citrus (satsuma mandarin, orange, lemon, lime, grapefruit) ), 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, 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, black beetle, cinnamon, tsuga, rat, pine, spruce, yew), oil trees (Jatrophacurcas, oil palm), 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, blue whale, etc.
Other: Flowers, foliage plants, etc.

  “Crop” also includes genetically modified crops.

When this active compound and this organophosphorus compound are used to control harmful animals (such as flies, mosquitoes, cockroaches) living in the house, the application amount of this active compound and this organophosphorus compound should be applied on the surface. When it is applied, it is usually 0.01 to 1000 mg per 1 m ^{2 of} processing area, and when applied to a space, it is usually 0.01 to 500 mg per 1 m ^{3 of} processing space.
Emulsions, wettable powders and flowables are usually diluted with water so that the concentration of the active compound and the organophosphorus compound is 0.1 to 1000 ppm, and are applied to oils, aerosols, smoke agents, poison baits. Apply the agent as it is.

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

  The production of this active compound will be shown as production examples.

¹Ｈ−ＮＭＲ（ＤＭＳＯ−Ｄ₆）δ：８．１１（１Ｈ，ｄ），８．５０（２Ｈ，ｓ），９．１８（１Ｈ，ｄ），９．６２（２Ｈ，ｓ）．
２，２，３，４，４，４−ヘキサフルオロ−１−ブタノール３．６４ｇおよびテトラヒドロフラン２０ｍＬの混合物に氷冷下で水素化ナトリウム（６０％油性）０．８１ｇを加え１０分間攪拌した。この混合物に４，６−ビス（［１，２，４］トリアゾール−１−イル）−ピリミジン４．２８ｇを加え、氷冷下で１５分間および室温で２時間攪拌した。反応混合物に水を注加し、酢酸エチルで抽出した。有機層を水洗した後、硫酸ナトリウムで乾燥し、減圧下に濃縮した。残渣をシリカゲルカラムクロマトグラフィーに付し、４−（２，２，３，４，４，４−ヘキサフルオロブチロキシ）−６−（［１，２，４］トリアゾール−１−イル）−ピリミジン５．１７ｇを得た。
４−（２，２，３，４，４，４−ヘキサフルオロブチロキシ）−６−（［１，２，４］トリアゾール−１−イル）−ピリミジン〈本活性化合物２７〉

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

¹ H-NMR (DMSO-D ₆ ) δ: 8.11 (1H, d), 8.50 (2H, s), 9.18 (1H, d), 9.62 (2H, s).
To a mixture of 3.64 g of 2,2,3,4,4,4-hexafluoro-1-butanol and 20 mL of tetrahydrofuran, 0.81 g of sodium hydride (60% oily) was added under ice cooling and stirred for 10 minutes. To this mixture, 4.28 g of 4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine was added, and the mixture was stirred for 15 minutes under ice cooling and for 2 hours at room temperature. Water was poured into the 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 residue was subjected to silica gel column chromatography to give 4- (2,2,3,4,4,4-hexafluorobutyroxy) -6-([1,2,4] triazol-1-yl) -pyrimidine 5 .17 g was obtained.
4- (2,2,3,4,4,4-Hexafluorobutyoxy) -6-([1,2,4] triazol-1-yl) -pyrimidine <active compound 27>

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：８．２６（２Ｈ，ｓ），８．９８（１Ｈ，ｓ），９．１２（２Ｈ，ｓ）．
５−クロロ−４，６−ビス（［１，２，４］トリアゾール−１−イル）−ピリミジン０．２７ｇ、ＮＭＰ２ｍＬ、ＤＢＵ０．１５ｇ及び２，２，３，４，４，４−ヘキサフルオロ−１−ブタノール０．１８ｇの混合物を氷冷下で０．５時間攪拌した。反応混合物にクエン酸水溶液を注加し、酢酸エチルで抽出した。有機層を水洗した後、硫酸ナトリウムで乾燥し、減圧下に濃縮した。残渣をシリカゲルカラムクロマトグラフィーに付し、５−クロロ−４−（２，２，３，４，４，４−ヘキサフルオロブチロキシ）−６−（［１，２，４］トリアゾール−１−イル）−ピリミジン０．２０ｇを得た。
５−クロロ−４−（２，２，３，４，４，４−ヘキサフルオロブチロキシ）−６−（［１，２，４］トリアゾール−１−イル）−ピリミジン〈本活性化合物４８〉

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

¹ H-NMR (CDCl ₃ ) δ: 8.26 (2H, s), 8.98 (1H, s), 9.12 (2H, s).
5-chloro-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine 0.27 g, NMP 2 mL, DBU 0.15 g and 2,2,3,4,4,4-hexafluoro- A mixture of 0.18 g of 1-butanol was stirred for 0.5 hour under ice cooling. An aqueous citric acid solution was poured into the 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 residue was subjected to silica gel column chromatography to give 5-chloro-4- (2,2,3,4,4,4-hexafluorobutyroxy) -6-[[1,2,4] triazol-1-yl. ) -Pyrimidine 0.20 g was obtained.
5-Chloro-4- (2,2,3,4,4,4-hexafluorobutyroxy) -6-([1,2,4] triazol-1-yl) -pyrimidine <active compound 48>

¹Ｈ−ＮＭＲ（ＤＭＳＯ−Ｄ₆）δ：８．５２（２Ｈ，ｓ），９．０３（１Ｈ，ｓ），９．５３（２Ｈ，ｓ）．
５−フルオロ−４，６−ビス（［１，２，４］トリアゾール−１−イル）−ピリミジン０．４６ｇ、ＮＭＰ４ｍＬ及び２，２，３，４，４，４−ヘキサフルオロ−１−ブタノール０．３６ｇの混合物に氷冷下でＤＢＵ０．３０ｇを加えた。この混合物を氷冷下０．５時間攪拌した。反応混合物にクエン酸水溶液を注加し、酢酸エチルで抽出した。有機層を水洗した後、硫酸ナトリウムで乾燥し、減圧下に濃縮した。残渣をシリカゲルカラムクロマトグラフィーに付し、５−フルオロ−４−（２，２，３，４，４，４−ヘキサフルオロブチロキシ）−６−（［１，２，４］トリアゾール−１−イル）−ピリミジン０．３７ｇを得た。
５−フルオロ−４−（２，２，３，４，４，４−ヘキサフルオロブチロキシ）−６−（［１，２，４］トリアゾール−１−イル）−ピリミジン〈本活性化合物５４〉

Production Example 3
To a mixture of 8.29 g of 1,2,4-triazole, 50 mL of acetonitrile and 15.5 g of N-ethyldiisopropylamine, 6.70 g of 4,5,6-trifluoropyrimidine was added dropwise at room temperature. The mixture was stirred at room temperature for 2 hours. The reaction mixture was filtered to collect the solid. This solid was washed successively with acetonitrile and water and then dried to obtain 8.95 g of 5-fluoro-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine.
5-Fluoro-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine

¹ H-NMR (DMSO-D ₆ ) δ: 8.52 (2H, s), 9.03 (1H, s), 9.53 (2H, s).
0.46 g of 5-fluoro-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine, 4 mL of NMP and 2,2,3,4,4,4-hexafluoro-1-butanol 0 To the .36 g mixture, 0.30 g of DBU was added under ice cooling. This mixture was stirred for 0.5 hour under ice cooling. An aqueous citric acid solution was poured into the 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 residue was subjected to silica gel column chromatography to give 5-fluoro-4- (2,2,3,4,4,4-hexafluorobutyoxy) -6-[[1,2,4] triazol-1-yl. ) -Pyrimidine 0.37 g was obtained.
5-Fluoro-4- (2,2,3,4,4,4-hexafluorobutyroxy) -6-([1,2,4] triazol-1-yl) -pyrimidine <active compound 54>

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：４．７１−４．８８（２Ｈ，ｍ），４．９５−５．１８（１Ｈ，ｍ），６．９１−６．９３（１Ｈ，ｍ），８．６２−８．６４（１Ｈ，ｍ）．
６−クロロ−４−（２，２，３，４，４，４−ヘキサフルオロブチロキシ）−ピリミジン１．４７ｇ、ヒドラジン１水和物０．５ｇ及びトリエチルアミン０．６０ｇの混合物を７０℃で２時間攪拌した。の混合物を室温まで冷却した。この反応混合物に水を注加し、酢酸エチルで抽出した。有機層を水洗した後、硫酸ナトリウムで乾燥し、減圧下に濃縮した。得られた結晶を濾過により集め、乾燥して、４−（２，２，３，４，４，４−ヘキサフルオロブチロキシ）−６−ヒドラジノピリミジン０．６０ｇを得た。
４−（２，２，３，４，４，４−ヘキサフルオロブチロキシ）−６−ヒドラジノピリミジン

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：３．７６（２Ｈ，ｓ），４．６７−４．８０（２Ｈ，ｍ），４．９７−５．２１（１Ｈ，ｍ），６．２１（１Ｈ，ｓ），６．２４（１Ｈ，ｓ），８．２５（１Ｈ，ｓ）．
４−（２，２，３，４，４，４−ヘキサフルオロブチロキシ）−６−ヒドラジノピリミジン０．５ｇ及びアセトニトリル４ｍＬの混合物に氷冷下でエチル−Ｎ−シアノ−ホルムイミデート０．１７ｇ及びアセトニトリル２ｍＬの混合物を加えた。この混合物を５０℃で２時間攪拌した。反応混合物に水を注加し、酢酸エチルで抽出した。有機層を水洗した後、硫酸ナトリウムで乾燥し、減圧下に濃縮した。残渣をシリカゲルカラムクロマトグラフィーに付し、６−｛５−アミノ−［１，２，４］トリアゾール−１−イル｝−４−（２，２，３，４，４，４−ヘキサフルオロブチロキシ）−ピリミジン６．９ｇを得た。
６−｛５−アミノ−［１，２，４］トリアゾール−１−イル｝−４−（２，２，３，４，４，４−ヘキサフルオロブチロキシ）−ピリミジン〈本活性化合物５８〉

Production Example 4
To a mixture of 9.0 g of 2,2,3,4,4,4-hexafluoro-1-butanol and 50 mL of tetrahydrofuran, 2.0 g of sodium hydride (60% oily) was added under ice cooling and stirred for 10 minutes. To this mixture, 7.45 g of 4,6-dichloropyrimidine was added and stirred at room temperature for 1 day. Water was poured into the 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 residue was subjected to silica gel column chromatography to obtain 6.9 g of 6-chloro-4- (2,2,3,4,4,4-hexafluorobutyroxy) -pyrimidine.
6-Chloro-4- (2,2,3,4,4,4-hexafluorobutyroxy) -pyrimidine

¹ H-NMR (CDCl ₃ ) δ: 4.71-4.88 (2H, m), 4.95-5.18 (1H, m), 6.91-6.93 (1H, m), 8 .62-8.64 (1H, m).
A mixture of 1.47 g of 6-chloro-4- (2,2,3,4,4,4-hexafluorobutyroxy) -pyrimidine, 0.5 g of hydrazine monohydrate and 0.60 g of triethylamine at 70 ° C. Stir for hours. The mixture was cooled to room temperature. Water was poured into the 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 crystals were collected by filtration and dried to obtain 0.60 g of 4- (2,2,3,4,4,4-hexafluorobutyroxy) -6-hydrazinopyrimidine.
4- (2,2,3,4,4,4-Hexafluorobutyoxy) -6-hydrazinopyrimidine

¹ H-NMR (CDCl ₃ ) δ: 3.76 (2H, s), 4.67-4.80 (2H, m), 4.97-5.21 (1H, m), 6.21 (1H , S), 6.24 (1H, s), 8.25 (1H, s).
Ethyl-N-cyano-formimidate was added to a mixture of 0.5 g of 4- (2,2,3,4,4,4-hexafluorobutyroxy) -6-hydrazinopyrimidine and 4 mL of acetonitrile under ice cooling. A mixture of 17 g and 2 mL of acetonitrile was added. The mixture was stirred at 50 ° C. for 2 hours. Water was poured into the 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 residue was subjected to silica gel column chromatography to give 6- {5-amino- [1,2,4] triazol-1-yl} -4- (2,2,3,4,4,4-hexafluorobutyroxy. ) -Pyrimidine 6.9g was obtained.
6- {5-amino- [1,2,4] triazol-1-yl} -4- (2,2,3,4,4,4-hexafluorobutyroxy) -pyrimidine <active compound 58>

¹Ｈ−ＮＭＲ（ＤＭＳＯ−Ｄ₆）δ：８．５１（２Ｈ，ｓ），９．３３（１Ｈ，ｓ），９．７１（２Ｈ，ｓ）．
５−ニトロ−４，６−ビス（［１，２，４］トリアゾール−１−イル）−ピリミジン１．０４ｇ、ＮＭＰ１２ｍＬ及び２，２，３，４，４，４−ヘキサフルオロ−１−ブタノール０．７３ｇの混合物に氷冷下でし、ＤＢＵ０．６１ｇを滴下した。この混合物を氷冷下で０．５時間攪拌した。反応混合物にクエン酸水溶液を注加し、酢酸エチルで抽出した。有機層を水洗した後、硫酸ナトリウムで乾燥し、減圧下に濃縮した。残渣をシリカゲルカラムクロマトグラフィーに付し、４−（２，２，３，４，４，４−ヘキサフルオロブチロキシ）−５−ニトロ−６−（［１，２，４］トリアゾール−１−イル）−ピリミジン０．５５ｇを得た。
４−（２，２，３，４，４，４−ヘキサフルオロブチロキシ）−５−ニトロ−６−（［１，２，４］トリアゾール−１−イル）−ピリミジン〈本活性化合物６１〉

４−（２，２，３，４，４，４−ヘキサフルオロブチロキシ）−５−ニトロ−６−（［１，２，４］トリアゾール−１−イル）−ピリミジン０．３７ｇ、酢酸エチル１０ｍＬ及び１０％Ｐｄ／Ｃの混合物を、約１気圧の水素雰囲気下、室温で２時間で攪拌した。反応混合物を濾過し、濾液を水洗した後、硫酸ナトリウムで乾燥し、減圧下で濃縮した。残渣をシリカゲルカラムクロマトグラフィーに付し、５−アミノ−４−（２，２，３，４，４，４−ヘキサフルオロブチロキシ）−６−（［１，２，４］トリアゾール−１−イル）−ピリミジン０．２９ｇを得た。
５−アミノ−４−（２，２，３，４，４，４−ヘキサフルオロブチロキシ）−６−（［１，２，４］トリアゾール−１−イル）−ピリミジン〈本活性化合物６０〉

Production Example 5
To a mixture of 3.32 g of 1,2,4-triazole, 20 mL of acetonitrile and 6.20 g of N-ethyldiisopropylamine, 3.88 g of 4,6-dichloro-5-nitropyrimidine was added at room temperature. The mixture was stirred at room temperature for 4 hours. The reaction mixture was filtered, and the residue was washed with acetonitrile and dried to obtain 1.40 g of 5-nitro-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine.
5-Nitro-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine

¹ H-NMR (DMSO-D ₆ ) δ: 8.51 (2H, s), 9.33 (1H, s), 9.71 (2H, s).
5-nitro-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine 1.04 g, NMP 12 mL and 2,2,3,4,4,4-hexafluoro-1-butanol 0 .73 g of the mixture was cooled with ice, and 0.61 g of DBU was added dropwise. The mixture was stirred for 0.5 hour under ice cooling. An aqueous citric acid solution was poured into the 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 residue was subjected to silica gel column chromatography, and 4- (2,2,3,4,4,4-hexafluorobutyroxy) -5-nitro-6-[[1,2,4] triazol-1-yl ) -Pyrimidine (0.55 g) was obtained.
4- (2,2,3,4,4,4-Hexafluorobutyoxy) -5-nitro-6-[[1,2,4] triazol-1-yl) -pyrimidine <active compound 61>

4- (2,2,3,4,4,4-Hexafluorobutyoxy) -5-nitro-6-[[1,2,4] triazol-1-yl) -pyrimidine 0.37 g, ethyl acetate 10 mL And a mixture of 10% Pd / C was stirred at room temperature for 2 hours under a hydrogen atmosphere of about 1 atm. The reaction mixture was filtered, and the filtrate was washed with water, dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 5-amino-4- (2,2,3,4,4,4-hexafluorobutyroxy) -6-[[1,2,4] triazol-1-yl. ) -Pyrimidine (0.29 g) was obtained.
5-Amino-4- (2,2,3,4,4,4-hexafluorobutyroxy) -6-([1,2,4] triazol-1-yl) -pyrimidine <active compound 60>

¹Ｈ−ＮＭＲ（ＤＭＳＯ−Ｄ₆）δ：２．５６（３Ｈ，ｓ），８．４５（２Ｈ，ｓ），９．１１（１Ｈ，ｓ），９．４０（２Ｈ，ｓ）．
５−メチル−４，６−ビス（［１，２，４］トリアゾール−１−イル）−ピリミジン０．４６ｇ、ＮＭＰ４ｍＬ及び２，２，３，４，４，４−ヘキサフルオロ−１−ブタノール０．３６ｇの混合物に氷冷下でＤＢＵ０．３０ｇを加えた。この混合物を１時間攪拌した。反応混合物にクエン酸水溶液を注加し、酢酸エチルで抽出した。有機層を水洗した後、硫酸ナトリウムで乾燥し、減圧下に濃縮した。残渣をシリカゲルカラムクロマトグラフィーに付し、４−（２，２，３，４，４，４−ヘキサフルオロブチロキシ）−５−メチル−６−（［１，２，４］トリアゾール−１−イル）−ピリミジン０．５０ｇを得た。
４−（２，２，３，４，４，４−ヘキサフルオロブチロキシ）−５−メチル−６−（［１，２，４］トリアゾール−１−イル）−ピリミジン〈本活性化合物６２〉

Production Example 6
To a mixture of 2.65 g of 1,2,4-triazole, 10 mL of acetonitrile and 4.96 g of N-ethyldiisopropylamine, 2.61 g of 4,6-dichloro-5-methylpyrimidine was added at room temperature. The mixture was heated to reflux for 14 hours. The cooled reaction mixture was filtered to collect the solid. This solid was washed with acetonitrile and then dried to obtain 2.12 g of 5-methyl-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine.
5-Methyl-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine

¹ H-NMR (DMSO-D ₆ ) δ: 2.56 (3H, s), 8.45 (2H, s), 9.11 (1H, s), 9.40 (2H, s).
0.46 g of 5-methyl-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine, 4 mL of NMP and 2,2,3,4,4,4-hexafluoro-1-butanol 0 To the .36 g mixture, 0.30 g of DBU was added under ice cooling. The mixture was stirred for 1 hour. An aqueous citric acid solution was poured into the 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 residue was subjected to silica gel column chromatography, and 4- (2,2,3,4,4,4-hexafluorobutyroxy) -5-methyl-6-[[1,2,4] triazol-1-yl ) -Pyrimidine 0.50 g was obtained.
4- (2,2,3,4,4,4-Hexafluorobutyroxy) -5-methyl-6-[[1,2,4] triazol-1-yl) -pyrimidine <active compound 62>

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：２．２９（３Ｈ，ｓ），４．７４−４．８７（２Ｈ，ｍ），４．９２−５．１５（１Ｈ，ｍ），８．４６（１Ｈ，ｓ）． The active compound 62 can also be synthesized by the following production method.
A mixture of 5 g of 4,6-dichloro-5-methylpyrimidine, 5.58 g of 2,2,3,4,4,4-hexafluorobutanol and 30 mL of NMP was ice-cooled, 5.6 g of DBU was added, and the mixture was stirred at room temperature for 1 day. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 7.84 g of 4-chloro-6- (2,2,3,4,4,4-hexafluorobutyroxy) -5-methylpyrimidine.
4-chloro-6- (2,2,3,4,4,4-hexafluorobutyroxy) -5-methylpyrimidine

¹ H-NMR (CDCl ₃ ) δ: 2.29 (3H, s), 4.74-4.87 (2H, m), 4.92-5.15 (1H, m), 8.46 (1H , S).

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：２．７６（３Ｈ，ｓ），８．１７（１Ｈ，ｓ），８．７５（１Ｈ，ｓ），９．１４（１Ｈ，ｓ）．
４−クロロ−５−メチル−６−（［１，２，４］トリアゾール−１−イル）−ピリミジン０．３９ｇ、２，２，３，４，４，４−ヘキサフルオロブタノール０．３６ｇおよびＮＭＰ４ｍＬの混合物に、ＤＢＵ０．３７ｇを加え室温で３０分間攪拌した。反応混合物に水を注加し、酢酸エチルで抽出した。有機層を水洗した後、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カラムクロマトグラフィーに付し、４−（２，２，３，４，４，４−ヘキサフルオロブチロキシ）−５−メチル−６−（［１，２，４］トリアゾール−１−イル）−ピリミジン０．３５ｇを得た。＜本活性化合物６２＞ 4-chloro-6- (2,2,3,4,4,4-hexafluorobutyroxy) -5-methylpyrimidine 0.62 g, 1,2,4-triazole 0.15 g, DBU 0.35 g and NMP 3 mL The mixture was stirred at 50 ° C. for 1 hour, stirred at 100 ° C. for 1 hour and 130 ° C. for 6 hours. Water was poured into the 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 column chromatography, and 4- (2,2,3,4,4,4-hexafluorobutyroxy) -5-methyl-6-[[1,2,4] triazole- 0.33 g of 1-yl) -pyrimidine was obtained. <Active compound 62>

A mixture of 3.26 g of 4,6-dichloro-5-methylpyrimidine and 30 mL of tetrahydrofuran was ice-cooled, 2.02 g of 1,2,4-triazole sodium was added, and the mixture was stirred at room temperature for 3 hours. Stir at 7 ° C. for 7 hours. Water was poured into the 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 column chromatography to obtain 1.35 g of 4-chloro-5-methyl-6-[[1,2,4] triazol-1-yl) -pyrimidine.
4-Chloro-5-methyl-6-([1,2,4] triazol-1-yl) -pyrimidine

¹ H-NMR (CDCl ₃ ) δ: 2.76 (3H, s), 8.17 (1H, s), 8.75 (1H, s), 9.14 (1H, s).
4-Chloro-5-methyl-6-([1,2,4] triazol-1-yl) -pyrimidine 0.39 g, 2,2,3,4,4,4-hexafluorobutanol 0.36 g and NMP 4 mL To this mixture, 0.37 g of DBU was added and stirred at room temperature 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 sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, and 4- (2,2,3,4,4,4-hexafluorobutyroxy) -5-methyl-6-[[1,2,4] triazole- 0.35 g of 1-yl) -pyrimidine was obtained. <Active compound 62>

¹Ｈ−ＮＭＲ（ＤＭＳＯ−Ｄ₆）δ：８．４７（２Ｈ，ｓ），９．２６（１Ｈ，ｓ），９．３５（２Ｈ，ｓ）．
５−ブロモ−４，６−ビス（［１，２，４］トリアゾール−１−イル）−ピリミジン０．４４ｇ、ＮＭＰ３ｍＬ及び２，２，３，４，４，４−ヘキサフルオロ−１−ブタノール０．２７ｇの混合物に氷冷下でＤＢＵ０．２３ｇを加えた。反応混合物にクエン酸水溶液を注加した。この混合物を酢酸エチルで抽出した。有機層を水洗し、硫酸ナトリウムで乾燥後、減圧下に濃縮した。残渣をシリカゲルカラムクロマトグラフィーに付し、５−ブロモ−４−（２，２，３，４，４，４−ヘキサフルオロブチロキシ）−６−（［１，２，４］トリアゾール−１−イル）−ピリミジン０．５１ｇを得た。
５−ブロモ−４−（２，２，３，４，４，４−ヘキサフルオロブチロキシ）−６−（［１，２，４］トリアゾール−１−イル）−ピリミジン〈本活性化合物６９〉

Production Example 7
To a mixture of 4.14 g of 1,2,4-triazole, 30 mL of acetonitrile and 7.75 g of N-ethyldiisopropylamine, 3.41 g of 5-bromo-4,6-dichloropyrimidine was added at room temperature. The mixture was stirred at room temperature for 8 hours. The reaction mixture was filtered to collect the solid. This solid was washed with acetonitrile and then dried to obtain 2.46 g of 5-bromo-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine.
5-Bromo-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine

¹ H-NMR (DMSO-D ₆ ) δ: 8.47 (2H, s), 9.26 (1H, s), 9.35 (2H, s).
5-Bromo-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine 0.44 g, NMP 3 mL and 2,2,3,4,4,4-hexafluoro-1-butanol 0 0.23 g of DBU was added to .27 g of the mixture under ice cooling. An aqueous citric acid solution was poured into the reaction mixture. This mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 5-bromo-4- (2,2,3,4,4,4-hexafluorobutyroxy) -6-[[1,2,4] triazol-1-yl. ) -Pyrimidine (0.51 g) was obtained.
5-Bromo-4- (2,2,3,4,4,4-hexafluorobutyroxy) -6-([1,2,4] triazol-1-yl) -pyrimidine <active compound 69>

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：０．８２（９Ｈ，ｓ），２．３６（２Ｈ，ｄ），７．３６（１Ｈ，ｓ），８．２３（２Ｈ，ｓ），８．４４（１Ｈ，ｓ），９．１１（２Ｈ，ｓ）．
５−ネオペンチルアミノ−４，６−ビス（［１，２，４］トリアゾール−１−イル）−ピリミジン０．３０ｇ、ＮＭＰ１ｍＬ及び２，２，３，４，４，４−ヘキサフルオロ−１−ブタノール０．１８ｇの混合物に氷冷下でＤＢＵ０．１５ｇを加えた。この混合物を室温で１２時間攪拌した。反応混合物にクエン酸水溶液を注加し、酢酸エチルで抽出した。有機層を水洗した後、硫酸ナトリウムで乾燥し、減圧下に濃縮した。残渣をシリカゲルカラムクロマトグラフィーに付し、４−（２，２，３，４，４，４−ヘキサフルオロブチロキシ）−５−ネオペンチルアミノ−６−（［１，２，４］トリアゾール−１−イル）−ピリミジン０．３１ｇを得た。
４−（２，２，３，４，４，４−ヘキサフルオロブチロキシ）−５−ネオペンチルアミノ−６−（［１，２，４］トリアゾール−１−イル）−ピリミジン〈本活性化合物７４〉

Production Example 9
A mixture of 3.48 g of 5-fluoro-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine, 45 mL of NMP and 2.62 g of neopentylamine was stirred at room temperature for 6 hours. An aqueous citric acid solution was poured into the 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. To the residue was added tret-butyl methyl ether, followed by filtration, and the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.41 g of 5-neopentylamino-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine.
5-Neopentylamino-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine

¹ H-NMR (CDCl ₃ ) δ: 0.82 (9H, s), 2.36 (2H, d), 7.36 (1H, s), 8.23 (2H, s), 8.44 ( 1H, s), 9.11 (2H, s).
5-Neopentylamino-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine 0.30 g, NMP 1 mL and 2,2,3,4,4,4-hexafluoro-1- To a mixture of 0.18 g of butanol, 0.15 g of DBU was added under ice cooling. The mixture was stirred at room temperature for 12 hours. An aqueous citric acid solution was poured into the 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 residue was subjected to silica gel column chromatography to give 4- (2,2,3,4,4,4-hexafluorobutyroxy) -5-neopentylamino-6-[[1,2,4] triazole-1 0.31 g of -yl) -pyrimidine was obtained.
4- (2,2,3,4,4,4-hexafluorobutyoxy) -5-neopentylamino-6-([1,2,4] triazol-1-yl) -pyrimidine <active compound 74 >

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：１．２８（３Ｈ，ｔ），３．４８（２Ｈ，ｑ），８．２１（２Ｈ，ｓ），８．８８（１Ｈ，ｓ），９．１５（２Ｈ，ｓ）．
５−エチル−４，６−ビス（［１，２，４］トリアゾール−１−イル）−ピリミジン０．４８ｇ、ＮＭＰ４ｍＬ及び２，２，３，４，４，４−ヘキサフルオロ−１−ブタノール０．３６ｇの混合物に、室温でＤＢＵ０．３０ｇを加えた。この混合物を室温で２時間攪拌した。反応混合物にクエン酸水溶液を注加し、酢酸エチルで抽出した。有機層を水洗した後、硫酸ナトリウムで乾燥し、減圧下に濃縮した。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−（２，２，３，４，４，４−ヘキサフルオロブチロキシ）−６−（［１，２，４］トリアゾール−１−イル）−ピリミジン０．５８ｇを得た。
５−エチル−４−（２，２，３，４，４，４−ヘキサフルオロブチロキシ）−６−（［１，２，４］トリアゾール−１−イル）−ピリミジン〈本活性化合物７７〉

Production Example 10
To a mixture of 6.91 g of 1,2,4-triazole, 12.5 mL of acetonitrile and 12.9 g of N, N diisopropylethylamine, 4.43 g of 4,6-dichloro-5-ethylpyrimidine was added at room temperature. The mixture was heated to reflux for 11 hours. The cooled reaction mixture was concentrated under reduced pressure, and then filtered to collect a solid. This solid was washed with acetonitrile and dried to give 4.89 g of 5-ethyl-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine.
5-ethyl-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine

¹ H-NMR (CDCl ₃ ) δ: 1.28 (3H, t), 3.48 (2H, q), 8.21 (2H, s), 8.88 (1H, s), 9.15 ( 2H, s).
0.48 g of 5-ethyl-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine, 4 mL of NMP and 2,2,3,4,4,4-hexafluoro-1-butanol 0 To the .36 g mixture was added 0.30 g DBU at room temperature. The mixture was stirred at room temperature for 2 hours. An aqueous citric acid solution was poured into the 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 residue was subjected to silica gel column chromatography to give 5-ethyl-4- (2,2,3,4,4,4-hexafluorobutyroxy) -6-[[1,2,4] triazol-1-yl. ) -Pyrimidine (0.58 g) was obtained.
5-ethyl-4- (2,2,3,4,4,4-hexafluorobutyoxy) -6-([1,2,4] triazol-1-yl) -pyrimidine <active compound 77>

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：１．３１（６Ｈ，ｄ），３．６２−３．７２（１Ｈ，ｍ），８．２１（２Ｈ，ｓ），８．９０（１Ｈ，ｓ），８．９６（２Ｈ，ｓ）．
５−イソプロピル−４，６−ビス（［１，２，４］トリアゾール−１−イル）−ピリミジン０．５１ｇ、ＮＭＰ４ｍＬ及び２，２，３，４，４，４−ヘキサフルオロ−１−ブタノール０．３６ｇの混合物に、室温でＤＢＵ０．５１ｇを加えた。この混合物を室温で一晩攪拌した。反応混合物にクエン酸水溶液を注加し、酢酸エチルで抽出した。有機層を水洗した後、硫酸ナトリウムで乾燥し、減圧下に濃縮した。残渣をシリカゲルカラムクロマトグラフィーに付し、５−イソプロピル−４−（２，２，３，４，４，４−ヘキサフルオロブチロキシ）−６−（［１，２，４］トリアゾール−１−イル）−ピリミジン０．５８ｇを得た。
５−イソプロピル−４−（２，２，３，４，４，４−ヘキサフルオロブチロキシ）−６−（［１，２，４］トリアゾール−１−イル）−ピリミジン〈本活性化合物８５〉

Production Example 11
A mixture of 6.91 g of 1,2,4-triazole, 12.5 mL of acetonitrile, 12.9 g of N-ethyldiisopropylamine and 4.78 g of 4,6-dichloro-5-isopropylpyrimidine was heated to reflux for 18 hours. The reaction mixture allowed to cool was concentrated under reduced pressure. The residue was filtered to collect the solid. This solid was washed with acetonitrile and then dried to obtain 4.41 g of 5-isopropyl-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine.
5-Isopropyl-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine

¹ H-NMR (CDCl ₃ ) δ: 1.31 (6H, d), 3.62-3.72 (1H, m), 8.21 (2H, s), 8.90 (1H, s), 8.96 (2H, s).
5-isopropyl-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine 0.51 g, NMP 4 mL and 2,2,3,4,4,4-hexafluoro-1-butanol 0 To the .36 g mixture, 0.51 g DBU was added at room temperature. The mixture was stirred overnight at room temperature. An aqueous citric acid solution was poured into the 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 residue was subjected to silica gel column chromatography to give 5-isopropyl-4- (2,2,3,4,4,4-hexafluorobutyroxy) -6-([1,2,4] triazol-1-yl. ) -Pyrimidine (0.58 g) was obtained.
5-Isopropyl-4- (2,2,3,4,4,4-hexafluorobutyroxy) -6-([1,2,4] triazol-1-yl) -pyrimidine <active compound 85>

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：１．１８（９Ｈ，ｓ），８．２０（２Ｈ，ｓ），８．７７（１Ｈ，ｓ），８．８９（２Ｈ，ｓ）．
５−ｔｅｒｔ−ブチル−４，６−ビス（［１，２，４］トリアゾール−１−イル）−ピリミジン０．２３ｇ、ＮＭＰ１．５ｍＬ及び２，２，３，４，４，４−ヘキサフルオロ−１−ブタノール０．１５ｇの混合物に、室温でＤＢＵ０．１３ｇを加えた。この混合物を室温で一晩攪拌した。反応混合物にクエン酸水溶液を注加し、酢酸エチルで抽出した。有機層を水洗した後、硫酸ナトリウムで乾燥し、減圧下に濃縮した。残渣をシリカゲルカラムクロマトグラフィーに付し、５−ｔｅｒｔ−ブチル−４−（２，２，３，４，４，４−ヘキサフルオロブチロキシ）−６−（［１，２，４］トリアゾール−１−イル）−ピリミジン０．２１ｇを得た。
５−ｔｅｒｔ−ブチル−４−（２，２，３，４，４，４−ヘキサフルオロブチロキシ）−６−（［１，２，４］トリアゾール−１−イル）−ピリミジン〈本活性化合物８９〉

Production Example 12
To a mixture of 0.86 g of 1,2,4-triazole, 6 mL of tetrahydrofuran and 1.90 g of DBU, 0.64 g of 5-tert-butyl-4,6-dichloropyrimidine was added at room temperature. The mixture was stirred at room temperature for 8 hours. The reaction mixture was concentrated under reduced pressure. To the residue was added aqueous citric acid solution, 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 residue was subjected to silica gel column chromatography to obtain 0.45 g of 5-tert-butyl-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine.
5-tert-butyl-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine

¹ H-NMR (CDCl ₃ ) δ: 1.18 (9H, s), 8.20 (2H, s), 8.77 (1H, s), 8.89 (2H, s).
5-tert-butyl-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine 0.23 g, NMP 1.5 mL and 2,2,3,4,4,4-hexafluoro- To a mixture of 0.15 g of 1-butanol, 0.13 g of DBU was added at room temperature. The mixture was stirred overnight at room temperature. An aqueous citric acid solution was poured into the 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 residue was subjected to silica gel column chromatography to give 5-tert-butyl-4- (2,2,3,4,4,4-hexafluorobutyroxy) -6-([1,2,4] triazole-1 0.21 g of -yl) -pyrimidine was obtained.
5-tert-butyl-4- (2,2,3,4,4,4-hexafluorobutyroxy) -6-([1,2,4] triazol-1-yl) -pyrimidine <active compound 89 >

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：３．９１（３Ｈ，ｓ），８．２８（２Ｈ，ｓ），８．８７（１Ｈ，ｓ），９．２６（２Ｈ，ｓ）．
５−メトキシ−４，６−ビス（［１，２，４］トリアゾール−１−イル）−ピリミジン０．２４ｇ、ＮＭＰ２ｍＬ及び２，２，３，４，４，４−ヘキサフルオロ−１−ブタノール０．１８ｇの混合物に、室温でＤＢＵ０．１５ｇを加えた。この混合物を室温で０．５時間攪拌した。反応混合物にクエン酸水溶液を注加し、酢酸エチルで抽出した。有機層を水洗した後、硫酸ナトリウムで乾燥し、減圧下に濃縮した。残渣をシリカゲルカラムクロマトグラフィーに付し、４−（２，２，３，４，４，４−ヘキサフルオロブチロキシ）−５−メトキシ−６−（［１，２，４］トリアゾール−１−イル）−ピリミジン０．１９ｇを得た。
４−（２，２，３，４，４，４−ヘキサフルオロブチロキシ）−５−メトキシ−６−（［１，２，４］トリアゾール−１−イル）−ピリミジン〈本活性化合物１０７〉

Production Example 13
To a mixture of 2.76 g of 1,2,4-triazole, 5 mL of acetonitrile and 1.79 g of 4,6-dichloro-5-methoxypyrimidine, 5.17 g of N-ethyldiisopropylamine was added at room temperature. The mixture was heated to reflux for 6 hours. The cooled reaction mixture was filtered to collect hand solids. This solid was washed with acetonitrile and then dried to obtain 0.95 g of 5-methoxy-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine.
5-Methoxy-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine

¹ H-NMR (CDCl ₃ ) δ: 3.91 (3H, s), 8.28 (2H, s), 8.87 (1H, s), 9.26 (2H, s).
5-methoxy-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine 0.24 g, NMP 2 mL and 2,2,3,4,4,4-hexafluoro-1-butanol 0 To a .18 g mixture was added 0.15 g DBU at room temperature. The mixture was stirred at room temperature for 0.5 hours. An aqueous citric acid solution was poured into the 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 residue was subjected to silica gel column chromatography, and 4- (2,2,3,4,4,4-hexafluorobutyroxy) -5-methoxy-6-[[1,2,4] triazol-1-yl ) -Pyrimidine 0.19 g was obtained.
4- (2,2,3,4,4,4-hexafluorobutyoxy) -5-methoxy-6-([1,2,4] triazol-1-yl) -pyrimidine <active compound 107>

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：１．６４（６Ｈ，ｓ），９．４３（１Ｈ，ｓ）．
２−クロロ−２−メチルプロピオンアルデヒド３．９０ｇ及びジエチルエーテル３７ｍLの混合物に、水素化ホウ素ナトリウム１．６ｇを加えた。この混合物を室温で５時間攪拌した。反応混合物に水を注加し、ジエチルエーテルで抽出した。有機層を硫酸ナトリウムで乾燥し、残渣を蒸留することにより、２−クロロ−２−メチルプロパン−１−オール１．０ｇを得た。
２−クロロ−２−メチルプロパン−１−オール

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：１．５７−１．５９（６Ｈ，ｍ），１．９８−２．０６（１Ｈ，ｍ），３．５５−３．６１（２Ｈ，ｍ）．
５−メチル−４，６−ビス（［１，２，４］トリアゾール−１−イル）−ピリミジン０．２３ｇ、ＮＭＰ３ｍＬ及び２−クロロ−２−メチルプロパン−１−オール０．１９ｇの混合物に、氷冷下でＤＢＵ０．１６ｇを加えた。この混合物を５０℃で５時間攪拌した。室温に放冷した反応混合物に水を注加し、酢酸エチルで抽出した。有機層を水洗した後、硫酸ナトリウムで乾燥し、減圧下に濃縮した。残渣をシリカゲルカラムクロマトグラフィーに付し、４−（２−クロロ−２−メチルプロポキシ）−５−メチル−６−（［１，２，４］トリアゾール−１−イル）−ピリミジン０．１４ｇを得た。
４−（２−クロロ−２−メチルプロポキシ）−５−メチル−６−（［１，２，４］トリアゾール−１−イル）−ピリミジン〈本活性化合物１１０〉

Production Example 14
7.21 g of tert-butylamine was added to 7.21 g of isobutyraldehyde under ice cooling. The mixture was stirred at room temperature for 2 hours. Chloroform 100mL was added to the reaction mixture, and it dried with sodium sulfate. To the obtained solution, 14.0 g of N-chlorosuccinimide was added under ice cooling, and the mixture was stirred at room temperature for 5 hours. 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. Concentrated hydrochloric acid was added to the obtained residue. The mixture was stirred at room temperature for 5 hours. Sodium hydrogen carbonate was added to the reaction mixture, and the mixture was extracted with chloroform. The residue was distilled to obtain 3.90 g of 2-chloro-2-methylpropionaldehyde.
2-chloro-2-methylpropionaldehyde

¹ H-NMR (CDCl ₃ ) δ: 1.64 (6H, s), 9.43 (1H, s).
1.6 g of sodium borohydride was added to a mixture of 3.90 g of 2-chloro-2-methylpropionaldehyde and 37 mL of diethyl ether. The mixture was stirred at room temperature for 5 hours. Water was poured into the reaction mixture, and the mixture was extracted with diethyl ether. The organic layer was dried over sodium sulfate, and the residue was distilled to obtain 1.0 g of 2-chloro-2-methylpropan-1-ol.
2-Chloro-2-methylpropan-1-ol

¹ H-NMR (CDCl ₃ ) δ: 1.57-1.59 (6H, m), 1.98-2.06 (1H, m), 3.55-3.61 (2H, m).
To a mixture of 0.23 g 5-methyl-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine, 3 mL NMP and 0.19 g 2-chloro-2-methylpropan-1-ol, DBU0.16g was added under ice-cooling. The mixture was stirred at 50 ° C. for 5 hours. Water was poured into the reaction mixture allowed to cool to room temperature, 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 residue was subjected to silica gel column chromatography to obtain 0.14 g of 4- (2-chloro-2-methylpropoxy) -5-methyl-6-[[1,2,4] triazol-1-yl) -pyrimidine. It was.
4- (2-Chloro-2-methylpropoxy) -5-methyl-6-[[1,2,4] triazol-1-yl) -pyrimidine <active compound 110>

¹Ｈ−ＮＭＲ（ＤＭＳＯ−Ｄ₆）δ：８．５８（２Ｈ，ｓ），９．３６（１Ｈ，ｓ），９．６３（２Ｈ，ｓ）．
５−シアノ−４，６−ビス（［１，２，４］トリアゾール−１−イル）−ピリミジン０．２４ｇ、ＮＭＰ２ｍＬ及び２，２，３，４，４，４−ヘキサフルオロ−１−ブタノール０．１８ｇの混合物に−２０℃でＤＢＵ０．１５ｇを加えた。反応混合物でクエン酸水溶液を加え、酢酸エチルで抽出した。有機層を水洗し、硫酸ナトリウムで乾燥後、減圧下に濃縮した。残渣をシリカゲルカラムクロマトグラフィーに付し、５−シアノ−４−（２，２，３，４，４，４−ヘキサフルオロブチロキシ）−６−（［１，２，４］トリアゾール−１−イル）−ピリミジン０．２１ｇを得た。
５−シアノ−４−（２，２，３，４，４，４−ヘキサフルオロブチロキシ）−６−（［１，２，４］トリアゾール−１−イル）−ピリミジン〈本活性化合物１１５〉

Production Example 17
To a mixture of 1.33 g of 1,2,4-triazole, 4 mL of acetonitrile and 1.39 g of 4,6-dichloro-5-cyanopyrimidine, 2.48 g of N-ethyldiisopropylamine was added dropwise under ice cooling. The mixture was allowed to stand for 1 hour under ice cooling. The reaction mixture was filtered to collect the solid. The solid was washed with acetonitrile and dried to obtain 1.67 g of 5-cyano-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine.
5-Cyano-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine

¹ H-NMR (DMSO-D ₆ ) δ: 8.58 (2H, s), 9.36 (1H, s), 9.63 (2H, s).
5-cyano-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine 0.24 g, NMP 2 mL and 2,2,3,4,4,4-hexafluoro-1-butanol 0 0.15 g DBU was added to the -18 g mixture at -20 ° C. An aqueous citric acid solution was added to the 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 residue was subjected to silica gel column chromatography to give 5-cyano-4- (2,2,3,4,4,4-hexafluorobutyroxy) -6-[[1,2,4] triazol-1-yl. ) -Pyrimidine 0.21 g was obtained.
5-cyano-4- (2,2,3,4,4,4-hexafluorobutyroxy) -6-([1,2,4] triazol-1-yl) -pyrimidine <active compound 115>

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：２．５４（３Ｈ，ｓ），７．２７−７．２８（２Ｈ，ｍ），７．５５−７．５６（２Ｈ，ｍ），８．１８−８．１９（２Ｈ，ｍ），８．９１（１Ｈ，ｓ）．
４，６−ジ（イミダゾール−１−イル）−５−メチルピリミジン０．２３ｇ、ＮＭＰ２ｍＬ及び２，２，３，４，４，４−ヘキサフルオロ−１−ブタノール０．１８ｇの混合物に、室温でＤＢＵ０．１５ｇを加えた。この混合物を室温で一晩攪拌した。反応混合物にクエン酸水溶液を注加し、酢酸エチルで抽出した。有機層を水洗した後、硫酸ナトリウムで乾燥し、減圧下に濃縮した。残渣をシリカゲルカラムクロマトグラフィーに付し、４−（２，２，３，４，４，４−ヘキサフルオロブチロキシ）−６−（イミダゾール−１−イル）−５−メチルピリミジン０．２３ｇを得た。
４−（２，２，３，４，４，４−ヘキサフルオロブチロキシ）−６−（イミダゾール−１−イル）−５−メチルピリミジン〈本活性化合物１１７〉

Production Example 18
To a mixture of 7.03 g of imidazole, 30 mL of tetrahydrofuran and 5.61 g of 4,6-dichloro-5-methylpyrimidine, 15.7 g of DBU was added at room temperature. The mixture was stirred overnight. The reaction mixture was concentrated under reduced pressure and filtered to collect the solid. This solid was washed with acetonitrile and dried to obtain 1.93 g of 4,6-di (imidazol-1-yl) -5-methylpyrimidine.
4,6-di (imidazol-1-yl) -5-methylpyrimidine

¹ H-NMR (CDCl ₃ ) δ: 2.54 (3H, s), 7.27-7.28 (2H, m), 7.55-7.56 (2H, m), 8.18-8 .19 (2H, m), 8.91 (1H, s).
To a mixture of 0.23 g of 4,6-di (imidazol-1-yl) -5-methylpyrimidine, 2 mL of NMP and 0.18 g of 2,2,3,4,4,4-hexafluoro-1-butanol at room temperature DBU 0.15 g was added. The mixture was stirred overnight at room temperature. An aqueous citric acid solution was poured into the 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 residue was subjected to silica gel column chromatography to obtain 0.23 g of 4- (2,2,3,4,4,4-hexafluorobutyroxy) -6- (imidazol-1-yl) -5-methylpyrimidine. It was.
4- (2,2,3,4,4,4-Hexafluorobutyoxy) -6- (imidazol-1-yl) -5-methylpyrimidine <active compound 117>

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：７．２６−７．２７（２Ｈ，ｍ），７．８３−７．８４（２Ｈ，ｍ），８．４９−８．５０（２Ｈ，ｍ），８．８９（１Ｈ，ｓ）．
５−クロロ−４，６−ジ（イミダゾール−１−イル）−ピリミジン０．２５ｇ、ＮＭＰ２ｍＬ及び２，２，３，４，４，４−ヘキサフルオロ−１−ブタノール０．１８ｇの混合物に氷冷下でＤＢＵ０．１５ｇを加えた。この混合物を氷冷下０．５時間攪拌した。反応混合物にクエン酸水溶液を注加し、酢酸エチルで抽出した。有機層を水洗した後、硫酸ナトリウムで乾燥し、減圧下に濃縮した。残渣をシリカゲルカラムクロマトグラフィーに付し、５−クロロ−４−（２，２，３，４，４，４−ヘキサフルオロブチロキシ）−６−（イミダゾール−１−イル）−ピリミジン０．２１ｇを得た。
５−クロロ−４−（２，２，３，４，４，４−ヘキサフルオロブチロキシ）−６−（イミダゾール−１−イル）−ピリミジン〈本活性化合物１１９〉

Production Example 19
7.76 g of N, N-diisopropylethylamine was added to a mixture of 4.09 g of imidazole, 10 mL of acetonitrile and 3.67 g of 4,5,6-trichloropyrimidine under ice cooling. The mixture was left overnight at room temperature. The reaction mixture was filtered to collect the solid. This solid was washed with acetonitrile and then dried to obtain 3.20 g of 5-chloro-4,6-di (imidazol-1-yl) -pyrimidine.
5-Chloro-4,6-di (imidazol-1-yl) -pyrimidine

¹ H-NMR (CDCl ₃ ) δ: 7.26-7.27 (2H, m), 7.83-7.84 (2H, m), 8.49-8.50 (2H, m), 8 .89 (1H, s).
A mixture of 0.25 g of 5-chloro-4,6-di (imidazol-1-yl) -pyrimidine, 2 mL of NMP and 0.18 g of 2,2,3,4,4,4-hexafluoro-1-butanol was ice-cooled. Below, 0.15 g of DBU was added. This mixture was stirred for 0.5 hour under ice cooling. An aqueous citric acid solution was poured into the 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 residue was subjected to silica gel column chromatography to obtain 0.21 g of 5-chloro-4- (2,2,3,4,4,4-hexafluorobutyroxy) -6- (imidazol-1-yl) -pyrimidine. Obtained.
5-Chloro-4- (2,2,3,4,4,4-hexafluorobutyroxy) -6- (imidazol-1-yl) -pyrimidine <active compound 119>

¹Ｈ−ＮＭＲ（ＤＭＳＯ−Ｄ₆）δ：６．５９（１Ｈ，ｓ），８．３４（１Ｈ，ｓ），８．３８（１Ｈ，ｓ），９．２８（１Ｈ，ｓ）．
６−（［１，２，４］トリアゾール−１−イル）−ピリミジン−４−オール１．６３ｇ、１，４−ジオキサン１０ｍＬ及びローソン試薬３．０３ｇの混合物を、４時間加熱還流した。放冷した反応混合物を濾過して固体を集めた。この固体を１，４−ジオキサンで洗浄後、乾燥して、６−（［１，２，４］トリアゾール−１−イル）−ピリミジン−４−チオール１．６３ｇを得た。
６−（［１，２，４］トリアゾール−１−イル）−ピリミジン−４−チオール

¹Ｈ−ＮＭＲ（ＤＭＳＯ−Ｄ₆）δ：７．４５（１Ｈ，ｄ），８．４０（１Ｈ，ｓ），８．４８（１Ｈ，ｓ），９．３６（１Ｈ，ｓ），１４．４０（１Ｈ，ｂｒｓ）．
６−（［１，２，４］トリアゾール−１−イル）−ピリミジン−４−チオール０．５４ｇ、Ｎ，Ｎ−ジメチルホルムアミド３ｍＬ及びトリフルオロメタンスルホン酸 ２，２，３，４，４，４−ヘキサフルオロ−１−ブチル０．９４ｇの混合物に、室温で炭酸カリウム０．５０ｇを加えた。この混合物を室温で２時間攪拌した。反応混合物にクエン酸水溶液を注加し、酢酸エチルで抽出した。有機層を水洗した後、硫酸ナトリウムで乾燥し、減圧下に濃縮した。残渣をシリカゲルカラムクロマトグラフィーに付し、４−（２，２，３，４，４，４−ヘキサフルオロブチル−１−スルファニル）−６−（［１，２，４］トリアゾール−１−イル）−ピリミジン０．８８ｇを得た。
４−（２，２，３，４，４，４−ヘキサフルオロブチル−１−スルファニル）−６−（［１，２，４］トリアゾール−１−イル）−ピリミジン〈本活性化合物１３３〉

Production Example 20
A mixture of 2.3 g of 4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine and 20 mL of concentrated hydrochloric acid was heated to reflux for 4 hours. The reaction mixture was cooled to room temperature. Sodium bicarbonate was added to the reaction mixture. The precipitated crystals were collected by filtration. The crystals were dried to obtain 1.6 g of 6-([1,2,4] triazol-1-yl) -pyrimidin-4-ol.
6-([1,2,4] Triazol-1-yl) -pyrimidin-4-ol

¹ H-NMR (DMSO-D ₆ ) δ: 6.59 (1H, s), 8.34 (1H, s), 8.38 (1H, s), 9.28 (1H, s).
A mixture of 1.63 g of 6-([1,2,4] triazol-1-yl) -pyrimidin-4-ol, 10 mL of 1,4-dioxane and 3.03 g of Lawson's reagent was heated to reflux for 4 hours. The cooled reaction mixture was filtered to collect the solid. This solid was washed with 1,4-dioxane and dried to obtain 1.63 g of 6-([1,2,4] triazol-1-yl) -pyrimidine-4-thiol.
6-([1,2,4] Triazol-1-yl) -pyrimidine-4-thiol

¹ H-NMR (DMSO-D ₆ ) δ: 7.45 (1H, d), 8.40 (1H, s), 8.48 (1H, s), 9.36 (1H, s), 14. 40 (1H, brs).
6-([1,2,4] triazol-1-yl) -pyrimidine-4-thiol 0.54 g, 3 mL of N, N-dimethylformamide and trifluoromethanesulfonic acid 2,2,3,4,4,4- To a mixture of 0.94 g of hexafluoro-1-butyl, 0.50 g of potassium carbonate was added at room temperature. The mixture was stirred at room temperature for 2 hours. An aqueous citric acid solution was poured into the 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 residue was subjected to silica gel column chromatography, and 4- (2,2,3,4,4,4-hexafluorobutyl-1-sulfanyl) -6-[[1,2,4] triazol-1-yl) -0.88 g of pyrimidine was obtained.
4- (2,2,3,4,4,4-hexafluorobutyl-1-sulfanyl) -6-([1,2,4] triazol-1-yl) -pyrimidine <active compound 133>

Production Example 21
To a mixture of 0.23 g of 4,6-di (imidazol-1-yl) -5-methylpyrimidine, 2 mL of NMP and 0.10 g of (trimethylsilyl) methanol, 0.04 g of sodium hydride (60% oily) was added at room temperature. . The mixture was stirred at room temperature for 1 hour. An aqueous citric acid solution was poured into the reaction mixture, and the mixture was extracted twice with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.12 g of 6- (imidazol-1-yl) -5-methyl-4-{(trimethylsilyl) methoxy} pyrimidine.
6- (imidazol-1-yl) -5-methyl-4-{(trimethylsilyl) methoxy} pyrimidine <active compound 134>

Production Example 22
To a mixture of 0.23 g of 4,6-di (imidazol-1-yl) -5-methylpyrimidine, 2 mL of NMP and 0.12 g of 2- (trimethylsilyl) ethanol, 0.04 g of sodium hydride (60% oily) at room temperature. added. The mixture was stirred at room temperature for 1 hour. An aqueous citric acid solution was poured into the reaction mixture, and the mixture was extracted twice with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.13 g of 6- (imidazol-1-yl) -5-methyl-4- {2- (trimethylsilyl) ethoxy} pyrimidine.
6- (imidazol-1-yl) -5-methyl-4- {2- (trimethylsilyl) ethoxy} pyrimidine <active compound 135>

¹Ｈ−ＮＭＲ（ＤＭＳＯ−Ｄ₆）δ：２．１７（３Ｈ，ｓ），８．２４（１Ｈ，ｓ），８．３１（１Ｈ，ｓ），９．１３（１Ｈ，ｓ），１２．９４（１Ｈ，ｂｒｓ）．
５−メチル−６−（［１，２，４］トリアゾール−１−イル）−ピリミジン−４−オール２．８４ｇ、１，４−ジオキサン１５ｍＬ及びローソン試薬３．２４ｇの混合物を、６時間加熱還流した。放冷した反応混合物を濾過して固体を集めた。この固体を１，４−ジオキサンで洗浄後、乾燥して、５−メチル−６−（［１，２，４］トリアゾール−１−イル）−ピリミジン−４−チオール２．２４ｇを得た。
５−メチル−６−（［１，２，４］トリアゾール−１−イル）−ピリミジン−４−チオール

¹Ｈ−ＮＭＲ（ＤＭＳＯ−Ｄ₆）δ：２．４１（３Ｈ，ｓ），８．３５（１Ｈ，ｓ），８．３８（１Ｈ，ｓ），９．１８（１Ｈ，ｓ），１４．５２（１Ｈ，ｂｒｓ）．
５−メチル−６−（［１，２，４］トリアゾール−１−イル）−ピリミジン−４−チオール０．１９ｇ、Ｎ，Ｎ−ジメチルホルムアミド１ｍＬ及びトリフルオロメタンスルホン酸 ２，２，３，４，４，４−ヘキサフルオロ−１−ブチル０．３１ｇの混合物に、氷冷下で、炭酸カリウム０．１７ｇを加えた。この混合物を室温で１時間攪拌した。反応混合物に水を注加し、酢酸エチルで抽出した。有機層をクエン酸水溶液および水で順次洗浄した後、硫酸ナトリウムで乾燥し、減圧下に濃縮した。残渣をシリカゲルカラムクロマトグラフィーに付し、４−（２，２，３，４，４，４−ヘキサフルオロブチル−１−スルファニル）−５−メチル−６−（［１，２，４］トリアゾール−１−イル）−ピリミジン０．２７ｇを得た。
４−（２，２，３，４，４，４−ヘキサフルオロブチル−１−スルファニル）−５−メチル−６−（［１，２，４］トリアゾール−１−イル）−ピリミジン＜本活性化合物１３６＞

Production Example 23
A mixture of 4.56 g of 5-methyl-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine and 10 mL of concentrated hydrochloric acid was stirred at 70 ° C. for 4 hours. The reaction mixture was ice-cooled. To the reaction mixture was added 10% aqueous sodium hydroxide solution. The precipitated crystals were collected by filtration. The collected mass was dried to obtain 3.04 g of 5-methyl-6-([1,2,4] triazol-1-yl) -pyrimidin-4-ol.
5-Methyl-6-[[1,2,4] triazol-1-yl) -pyrimidin-4-ol

¹ H-NMR (DMSO-D ₆ ) δ: 2.17 (3H, s), 8.24 (1H, s), 8.31 (1H, s), 9.13 (1H, s), 12. 94 (1H, brs).
A mixture of 2.84 g of 5-methyl-6-[[1,2,4] triazol-1-yl) -pyrimidin-4-ol, 15 mL of 1,4-dioxane and 3.24 g of Lawson's reagent was heated to reflux for 6 hours. did. The cooled reaction mixture was filtered to collect the solid. This solid was washed with 1,4-dioxane and then dried to obtain 2.24 g of 5-methyl-6-[[1,2,4] triazol-1-yl) -pyrimidine-4-thiol.
5-Methyl-6-([1,2,4] triazol-1-yl) -pyrimidine-4-thiol

¹ H-NMR (DMSO-D ₆ ) δ: 2.41 (3H, s), 8.35 (1H, s), 8.38 (1H, s), 9.18 (1H, s), 14. 52 (1H, brs).
5-methyl-6-([1,2,4] triazol-1-yl) -pyrimidin-4-thiol 0.19 g, N, N-dimethylformamide 1 mL and trifluoromethanesulfonic acid 2,2,3,4, 0.17 g of potassium carbonate was added to a mixture of 0.31 g of 4,4-hexafluoro-1-butyl under ice cooling. The mixture was stirred at room temperature for 1 hour. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with aqueous citric acid solution and water, dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and 4- (2,2,3,4,4,4-hexafluorobutyl-1-sulfanyl) -5-methyl-6-[[1,2,4] triazole- 0.27 g of 1-yl) -pyrimidine was obtained.
4- (2,2,3,4,4,4-Hexafluorobutyl-1-sulfanyl) -5-methyl-6-[[1,2,4] triazol-1-yl) -pyrimidine <active compound 136>

Production Example 24
5-methyl-6-([1,2,4] triazol-1-yl) -pyrimidine-4-thiol 0.19 g, N, N-dimethylformamide 1 mL and trifluoromethanesulfonic acid 2,2,3,3- To a mixture of 0.26 g of tetrafluoro-1-propyl, 0.17 g of potassium carbonate was added under ice cooling. The mixture was stirred at room temperature for 1 hour. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with aqueous citric acid solution and water, dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and 5-methyl-4- (2,2,3,3-tetrafluoropropyl-1-sulfanyl) -6-[[1,2,4] triazol-1-yl). -0.21 g of pyrimidine was obtained.
5-Methyl-4- (2,2,3,3-tetrafluoropropyl-1-sulfanyl) -6-([1,2,4] triazol-1-yl) -pyrimidine <active compound 137>

Production Example 25
To a mixture of 0.39 g 5-methyl-6-[[1,2,4] triazol-1-yl) -pyrimidine-4-thiol, 5 mL N, N-dimethylformamide and 0.03 g potassium hydroxide at room temperature. Hexafluoropropene was added. The mixture was stirred at 60 ° C. for 1 hour. An aqueous citric acid solution was poured into the 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 residue was subjected to silica gel column chromatography, and (Z) -5-methyl-4- (1,2,3,3,3-pentafluoro-1-propenyl-1-sulfanyl) -6-([1,2, , 4] triazol-1-yl) -pyrimidine (0.26 g) was obtained.
(Z) -5-methyl-4- (1,2,3,3,3-pentafluoro-1-propenyl-1-sulfanyl) -6-([1,2,4] triazol-1-yl)- Pyrimidine <active compound 149>

Production Example 26
5-methyl-6-([1,2,4] triazol-1-yl) -pyrimidin-4-ol 0.35 g, 1,1,1-trifluoro-5-iodopentane 0.5 g, NMP 3 mL and carbonic acid A mixture of 0.75 g of cesium was stirred at 80 ° C. for 7 hours. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous ammonium chloride and water, dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and 4- (5,5,5-trifluoropentyloxy) -5-methyl-6-[[1,2,4] triazol-1-yl) -pyrimidine 0.05 g Got.
4- (5,5,5-trifluoropentyloxy) -5-methyl-6-[[1,2,4] triazol-1-yl) -pyrimidine <active compound 146>

式（Ｚ）で示される化合物０．８２ｇ、水素化トリブチルスズ０．５８ｇ、アゾジイソブチロニトリル０．０７ｇおよびトルエン５ｍＬの混合物を８０℃で１時間、１１０℃で１時間攪拌した。反応混合物に水を注加し、酢酸エチルで抽出した。硫酸ナトリウムで乾燥し、減圧下に濃縮した。残渣をシリカゲルカラムクロマトグラフィーに付し、４−（２，２，４，４，４−ペンタフルオロブチロキシ）−５−メチル−６−（［１，２，４］トリアゾール−１−イル）−ピリミジン０．４６ｇを得た。
４−（２，２，４，４，４−ペンタフルオロブチロキシ）−５−メチル−６−（［１，２，４］トリアゾール−１−イル）−ピリミジン＜本活性化合物１５０＞

Production Example 27
4- (3-Hydroxy-2,2,4,4,4-pentafluorobutyroxy) -5-methyl-6-[[1,2,4] triazol-1-yl) -pyrimidine 0.68 g and tetrahydrofuran 3 mL of the mixture was cooled to 0 ° C. and 0.03 g of sodium hydride and 0.38 g of phenyl chlorothiocarbonate were added. The mixture was stirred at room temperature for 30 minutes. 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 0.82 g of the compound represented by the formula (Z).

A mixture of 0.82 g of the compound represented by the formula (Z), 0.58 g of tributyltin hydride, 0.07 g of azodiisobutyronitrile and 5 mL of toluene was stirred at 80 ° C. for 1 hour and at 110 ° C. for 1 hour. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. Dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and 4- (2,2,4,4,4-pentafluorobutyroxy) -5-methyl-6-[[1,2,4] triazol-1-yl)- 0.46 g of pyrimidine was obtained.
4- (2,2,4,4,4-pentafluorobutyoxy) -5-methyl-6-([1,2,4] triazol-1-yl) -pyrimidine <active compound 150>

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：７．９３（１Ｈ，ｓ），８．１７（１Ｈ，ｓ），８．８９（１Ｈ，ｓ），９．２３（１Ｈ，ｓ）．
２，２−ビス（トリフルオロメチル）プロパノール０．２５ｇおよびテトラヒドロフラン４ｍＬの混合物に、６０％水素化ナトリウム（油性）０．０６ｇを加え２０分間攪拌した。ここへ４−クロロ−６−（［１，２，４］トリアゾール−１−イル）−ピリミジン０．２５ｇを加え室温で１日間攪拌した。反応混合物に水を注加し、酢酸エチルで抽出した。有機層を水洗した後、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カラムクロマトグラフィーに付し、４−（［１，２，４］トリアゾール−１−イル）−６−［２，２−ビス（トリフルオロメチル）プロポキシ］−ピリミジン０．１８ｇを得た。＜本活性化合物６＞

Production Example 28
A mixture of 7.0 g of 1,2,4-triazole and 100 mL of tetrahydrofuran was ice-cooled, 4 g of 60% sodium hydride (oil) was added, and the mixture was stirred for 15 minutes. 4,6-dichloropyrimidine 14.9g was added here, and it stirred at room temperature for 1 hour, Then, it stirred at 70 degreeC for 6 hours. Water was poured into the 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 column chromatography to obtain 7.0 g of 4-chloro-6-[[1,2,4] triazol-1-yl) -pyrimidine.
4-Chloro-6-[[1,2,4] triazol-1-yl) -pyrimidine

¹ H-NMR (CDCl ₃ ) δ: 7.93 (1H, s), 8.17 (1H, s), 8.89 (1H, s), 9.23 (1H, s).
To a mixture of 0.25 g of 2,2-bis (trifluoromethyl) propanol and 4 mL of tetrahydrofuran, 0.06 g of 60% sodium hydride (oil) was added and stirred for 20 minutes. To this was added 0.25 g of 4-chloro-6-[[1,2,4] triazol-1-yl) -pyrimidine, and the mixture was stirred at room temperature for 1 day. Water was poured into the 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 column chromatography to give 4-([1,2,4] triazol-1-yl) -6- [2,2-bis (trifluoromethyl) propoxy] -pyrimidine 0.18 g. Got. <Active compound 6>

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：４．８３（２Ｈ，ｔｔ），５．９６（１Ｈ，ｔｔ），６．９２（１Ｈ，ｓ），８．６２（１Ｈ，ｓ）．
４−クロロ−６−（２，２，３，３−テトラフルオロプロポキシ）−ピリミジン０．４９ｇ、１，２，４−トリアゾール０．１５ｇ、ＤＢＵ０．３７ｇおよびＮＭＰ３ｍＬの混合物を５０℃で１時間攪拌した後、８０℃で１時間攪拌した。反応混合物に水を注加し、酢酸エチルで抽出した。有機層を水洗した後、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カラムクロマトグラフィーに付し、４−（２，２，３，３−テトラフルオロプロポキシ）−６−（［１，２，４］トリアゾール−１−イル）−ピリミジン０．３９ｇを得た。＜本活性化合物１２＞

Production Example 29
To a mixture of 5 g of 4,6-dichloropyrimidine, 4.43 g of 2,2,3,3-tetrafluoropropanol and 70 mL of tetrahydrofuran, 1.4 g of 60% sodium hydride (oily) was added and stirred at room temperature for 1 hour. Water was poured into the 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 column chromatography to obtain 8.1 g of 4-chloro-6- (2,2,3,3-tetrafluoropropoxy) -pyrimidine.
4-Chloro-6- (2,2,3,3-tetrafluoropropoxy) -pyrimidine

¹ H-NMR (CDCl ₃ ) δ: 4.83 (2H, tt), 5.96 (1H, tt), 6.92 (1H, s), 8.62 (1H, s).
A mixture of 0.49 g of 4-chloro-6- (2,2,3,3-tetrafluoropropoxy) -pyrimidine, 0.15 g of 1,2,4-triazole, 0.37 g of DBU and 3 mL of NMP was stirred at 50 ° C. for 1 hour. Then, the mixture was stirred at 80 ° C. for 1 hour. Water was poured into the 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 column chromatography, and 4- (2,2,3,3-tetrafluoropropoxy) -6-([1,2,4] triazol-1-yl) -pyrimidine 0.39 g Got. <Active compound 12>

The active compound 12 can also be synthesized by the following production method.
To a mixture of 0.36 g of 4-chloro-6-[[1,2,4] triazol-1-yl) -pyrimidine, 0.24 g of 2,2,3,3-tetrafluoropropanol and 4 mL of NMP, 0.37 g of DBU was added. The mixture was further stirred at room temperature 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 sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 0.33 g of 4- (2,2,3,3-tetrafluoropropoxy) -6-([1,2,4] triazol-1-yl) -pyrimidine. Got. <Active compound 12>

Production Example 30
5-chloro-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine 0.5 g, NMP 5 mL and 2,2,3,3,4,4,5,5-octafluoropen A mixture of 0.46 g of ethanol was ice-cooled, 0.35 g of DBU was added, and the mixture was stirred at room temperature for 1 hour. Water was poured into the 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 column chromatography to give 5-chloro-4- (2,2,3,3,4,4,5,5-octafluoropentyloxy) -6-[[1,2, 4] 0.68 g of triazol-1-yl) -pyrimidine was obtained.
5-chloro-4- (2,2,3,3,4,4,5,5-octafluoropentyloxy) -6-[[1,2,4] triazol-1-yl) -pyrimidine <activities Compound 82>

Production Example 31
0.46 g of 5-methyl-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine, 3 mL of NMP and 2,2,3,3,4,4,5,5-octafluoropen DBU 0.33g was added to the mixture of 0.46g of tanol, and it stirred at room temperature for 1 hour. Water was poured into the 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 column chromatography to give 5-methyl-4- (2,2,3,3,4,4,5,5-octafluoropentyloxy) -6-[[1,2, 4] 0.68 g of triazol-1-yl) -pyrimidine was obtained.
5-methyl-4- (2,2,3,3,4,4,5,5-octafluoropentyloxy) -6-([1,2,4] triazol-1-yl) -pyrimidine <activities Compound 93>

式中のＲ¹、Ｒ²、Ｒ³、Ｇ¹およびＱは、下記の〔表１〕〜〔表８〕に記載の組合せを表す。 Hereinafter, this active compound manufactured by the manufacturing method according to the method as described in the above-mentioned Example manufacture example is illustrated.
A compound represented by the following formula:

R ¹ , R ² , R ³ , G ¹ and Q in the formula represent the combinations described in the following [Table 1] to [Table 8].

The ¹ H-NMR data of the active compounds described in [Table 1] to [Table 8] are shown below.

The active compound 1
¹ H-NMR (CDCl ₃ ) δ: 1.73 (3H, d), 6.11 (1H, q), 7.36 (1H, d), 8.13 (1H, s), 8.68 ( 1H, d), 9.19 (1H, s).
The active compound 2
¹ H-NMR (CDCl ₃ ) δ: 1.69-1.75 (3H, m), 6.07-6.14 (1H, m), 6.79 (1H, s), 7.21-7 .23 (1H, m), 7.59-7.64 (1H, m), 8.43-8.46 (1H, m), 8.68 (1H, s).
The active compound 3
¹ H-NMR (CDCl ₃ ) δ: 5.17 (2H, s), 7.43 (1H, d), 8.14 (1H, s), 8.69 (1H, s), 9.20 ( 1H, s).
The active compound 4
¹ H-NMR (CDCl ₃ ) δ: 5.15-5.17 (2H, m), 6.86-6.88 (1H, m), 7.22-7.24 (1H, m), 7 .62-7.65 (1H, m), 8.45-8.47 (1H, m), 8.68-8.69 (1H, m).
The active compound 5
¹ H-NMR (CDCl ₃ ) δ: 4.90 (2H, q), 7.38 (1H, d), 8.14 (1H, s), 8.69 (1H, d), 9.20 ( 1H, s).
The active compound 6
¹ H-NMR (CDCl ₃ ) δ: 1.54 (3H, s), 4.77 (2H, s), 7.31 (1H, s), 8.13 (1H, s), 8.68 ( 1H, s), 9.19 (1H, s).
The active compound 7
¹ H-NMR (CDCl ₃ ) δ: 5.34 (2H, s), 7.46 (1H, d), 8.14 (1H, s), 8.69 (1H, d), 9.21 ( 1H, s).
The active compound 8
¹ H-NMR (CDCl ₃ ) δ: 5.33 (2H, s), 6.89 (1H, d), 7.23-7.25 (1H, m), 7.64-7.65 (1H M), 8.46-8.47 (1H, m), 8.69 (1H, d).
The active compound 9
¹ H-NMR (CDCl ₃ ) δ: 1.80 (6H, s), 7.18 (1H, d), 8.03 (1H, s), 8.55 (1H, d), 9.10 ( 1H, s).
The active compound 10
¹ H-NMR (CDCl ₃ ) δ: 1.14 (6H, s), 3.55 (2H, s), 4.28 (2H, s), 7.25 (1H, d), 8.12 ( 1H, s), 8.65 (1H, d), 9.18 (1H, s).
The active compound 11
¹ H-NMR (CDCl ₃ ) δ: 1.14 (6H, s), 3.55 (2H, s), 4.28 (2H, s), 6.69 (1H, d), 7.21- 7.22 (1H, m), 7.61-7.62 (1H, m), 8.42-8.43 (1H, m), 8.65 (1H, d).
The active compound 12
¹ H-NMR (CDCl ₃ ) δ: 4.90 (2H, t), 6.02 (1H, tt), 7.36 (1H, s), 8.14 (1H, s), 8.70 ( 1H, s), 9.21 (1H, s).
The active compound 13
¹ H-NMR (CDCl ₃ ) δ: 4.87-4.90 (2H, m), 5.99 (1H, tt), 6.80 (1H, s), 7.23 (1H, s), 7.62 (1H, s), 8.44 (1H, s), 8.69 (1H, s).
The active compound 14
¹ H-NMR (CDCl ₃ ) δ: 4.94-5.01 (2H, m), 7.38 (1H, d), 8.14 (1H, s), 8.69 (1H, d), 9.20 (1H, s).
The active compound 15
¹ H-NMR (CDCl ₃ ) δ: 4.92-4.99 (2H, m), 6.81 (1H, d), 7.22-7.23 (1H, m), 7.61-7 .62 (1H, m), 8.44-8.45 (1H, m), 8.69 (1H, d).
The active compound 16
¹ H-NMR (CDCl ₃ ) δ: 4.11 (2H, q), 7.80 (1H, d), 8.14 (1H, s), 8.85 (1H, d), 9.21 ( 1H, s).
The active compound 17
¹ H-NMR (CDCl ₃ ) δ: 4.12 (2H, q), 7.22 (1H, s), 7.24 (1H, d), 7.62-7.63 (1H, m), 8.44 (1H, s), 8.84 (1H, s).
The active compound 18
¹ H-NMR (CDCl ₃ ) δ: 1.88 (6H, d), 6.72 (1H, d), 7.20-7.21 (1H, m), 7.59-7.60 (1H M), 8.41-8.42 (1H, m), 8.63 (1H, d).
The active compound 19
¹ H-NMR (CDCl ₃ ) δ: 4.96 (2H, t), 6.03 (1H, tt), 8.24 (1H, s), 8.51 (1H, s), 9.12 ( 1H, s).
The active compound 20
¹ H-NMR (CDCl ₃ ) δ: 4.90-4.97 (2H, m), 6.03 (1H, tt), 7.24-7.25 (1H, m), 7.82-7 .83 (1H, m), 8.45 (1H, s), 8.49 (1H, d).

The active compound 21
¹ H-NMR (CDCl ₃ ) δ: 1.56 (3H, d), 5.86-5.92 (1H, m), 7.33 (1H, d), 8.13 (1H, s), 8.67 (1H, d), 9.19 (1H, s).
The active compound 22
¹ H-NMR (CDCl ₃ ) δ: 1.55 (3H, d), 5.84-5.91 (1H, m), 6.76 (1H, s), 7.22 (1H, s), 7.61 (1H, s), 8.44 (1H, s), 8.66 (1H, d).
The active compound 23
¹ H-NMR (CDCl ₃ ) δ: 6.55-6.61 (1H, m), 7.51 (1H, d), 8.16 (1H, s), 8.74 (1H, d), 9.22 (1H, s).
The active compound 24
¹ H-NMR (CDCl ₃ ) δ: 6.55-6.61 (1H, m), 6.95 (1H, d), 7.24 (1H, s), 7.64-7.65 (1H M), 8.48 (1H, s), 8.73 (1H, d).
The active compound 25
¹ H-NMR (CDCl ₃ ) δ: 4.70-4.71 (2H, m), 4.82-4.83 (2H, m), 5.72-5.78 (1H, m), 7 .33 (1H, d), 8.12 (1H, s), 8.65 (1H, d), 9.18 (1H, s).
The active compound 26
¹ H-NMR (CDCl ₃ ) δ: 4.70-4.71 (2H, m), 4.82-4.83 (2H, m), 5.71-5.76 (1H, m), 6 .77 (1H, d), 7.21-7.22 (1H, m), 7.60-7.61 (1H, m), 8.42-8.43 (1H, m), 8.65 (1H, d).
The active compound 27
¹ H-NMR (CDCl ₃ ) δ: 4.84-4.89 (2H, m), 5.06-5.17 (1H, m), 7.36 (1H, s), 8.14 (1H , S), 8.70 (1H, s), 9.20 (1H, s).
The active compound 28
¹ H-NMR (CDCl ₃ ) δ: 4.85-4.89 (2H, m), 5.02-5.19 (1H, m), 6.80 (1H, d), 7.22-7 .23 (1H, m), 7.61-7.62 (1H, m), 8.44-8.45 (1H, m), 8.69 (1H, d).
The active compound 29
¹ H-NMR (CDCl ₃ ) δ: 1.58 (3H, d), 5.96-6.04 (1H, m), 7.31 (1H, d), 8.13 (1H, s), 8.67 (1H, d), 9.19 (1H, s).
The active compound 30
¹ H-NMR (CDCl ₃ ) δ: 1.57 (3H, d), 5.96-6.04 (1H, m), 6.75 (1H, d), 7.22 (1H, s), 7.61-7.62 (1H, m), 8.44 (1H, s), 8.67 (1H, s).
The active compound 31
¹ H-NMR (CDCl ₃ ) δ: 2.64-2.70 (2H, m), 4.69 (2H, t), 7.26 (1H, d), 8.12 (1H, s), 8.66 (1H, d), 9.19 (1H, s).
The active compound 32
¹ H-NMR (CDCl ₃ ) δ: 2.62-2.68 (2H, m), 4.68 (2H, t), 6.69 (1H, d), 7.21-7.22 (1H M), 7.60-7.61 (1H, m), 8.42-8.43 (1H, m), 8.66 (1H, d).
The active compound 33
¹ H-NMR (CDCl ₃ ) δ: 0.15 (9H, t), 4.13 (2H, s), 7.23 (1H, d), 8.11 (1H, s), 8.65 ( 1H, d), 9.18 (1H, s).
The active compound 34
¹ H-NMR (CDCl ₃ ) δ: 0.15 (9H, s), 4.13 (2H, s), 6.67 (1H, s), 7.21 (1H, s), 7.61 ( 1H, s), 8.42 (1H, s), 8.65 (1H, s).
The active compound 35
¹ H-NMR (CDCl ₃ ) δ: 0.10 (9H, s), 1.15-1.19 (2H, m), 4.52-4.56 (2H, m), 7.17 (1H , D), 8.11 (1H, s), 8.64 (1H, d), 9.18 (1H, s).
The active compound 36
¹ H-NMR (CDCl ₃ ) δ: 0.10 (9H, s), 1.14-1.18 (2H, m), 4.51-4.55 (2H, m), 6.61 (1H , D), 7.20-7.21 (1H, m), 7.59-7.60 (1H, m), 8.40-8.41 (1H, m), 8.64 (1H, d) ).
The active compound 37
¹ H-NMR (CDCl ₃ ) δ: 5.03 (2H, t), 6.08 (1H, tt), 7.38 (1H, d), 8.14 (1H, s), 8.69 ( 1H, d), 9.20 (1H, s).
The active compound 38
¹ H-NMR (CDCl ₃ ) δ: 5.01 (2H, t), 6.08 (1H, tt), 6.81 (1H, d), 7.22-7.23 (1H, m), 7.62-7.63 (1H, m), 8.44-8.45 (1H, m), 8.69 (1H, d).
The active compound 39
¹ H-NMR (CDCl ₃ ) δ: 4.83 (2H, d), 6.06 (1H, t), 6.77 (1H, d), 7.22 (1H, s), 7.61 ( 1H, d), 8.43 (1H, s), 8.66 (1H, s).
The active compound 40
¹ H-NMR (CDCl ₃ ) δ: 4.84 (2H, d), 6.07 (1H, t), 7.33 (1H, d), 8.13 (1H, s), 8.67 ( 1H, d), 9.19 (1H, s).

The active compound 41
¹ H-NMR (CDCl ₃ ) δ: 5.25-5.33 (2H, m), 7.33 (1H, d), 8.13 (1H, s), 8.67 (1H, d), 9.19 (1H, s).
The active compound 42
¹ H-NMR (CDCl ₃ ) δ: 2.35-2.43 (2H, m), 4.36 (2H, t), 4.41 (2H, t), 6.78 (1H, s), 7.97 (1H, s), 8.08 (1H, s), 8.56 (1H, s).
The active compound 43
¹ H-NMR (DMSO-D ₆ ) δ: 5.02 (2H, t), 6.56-6.88 (1H, m), 7.13 (1H, s), 7.72 (1H, s ), 7.79 (2H, brs), 8.80 (1H, s).
The active compound 44
¹ H-NMR (CDCl ₃ ) δ: 5.05-5.07 (2H, m), 5.46-5.49 (1H, m), 5.55-5.58 (1H, m), 7 .31-7.33 (1H, m), 8.13 (1H, s), 8.66 (1H, s), 9.19 (1H, s).
The active compound 45
¹ H-NMR (CDCl ₃ ) δ: 5.04-5.06 (2H, m), 5.47-5.49 (1H, m), 5.56-5.58 (1H, m), 6 .75 (1H, s), 7.21-7.23 (1H, m), 7.60-7.62 (1H, m), 8.43 (1H, s), 8.66 (1H, s) ).
The active compound 46
¹ H-NMR (CDCl ₃ ) δ: 5.33 (2H, s), 7.32 (1H, d), 8.13 (1H, s), 8.67 (1H, d), 9.19 ( 1H, s).
The active compound 47
¹ H-NMR (CDCl ₃ ) δ: 5.32 (2H, s), 6.76 (1H, d), 7.22 (1H, s), 7.60-7.62 (1H, m), 8.43 (1H, s), 8.67 (1H, d).
The active compound 48
¹ H-NMR (CDCl ₃ ) δ: 4.84-4.97 (2H, m), 5.07-5.24 (1H, m), 8.22 (1H, s), 8.63 (1H , S), 9.09 (1H, s).
The active compound 49
¹ H-NMR (CDCl ₃ ) δ: 4.92-4.96 (2H, m), 6.06 (1H, tt), 8.22 (1H, s), 8.63 (1H, s), 9.09 (1H, s).
The active compound 50
¹ H-NMR (CDCl ₃ ) δ: 5.22 (2H, s), 8.22 (1H, s), 8.63 (1H, s), 9.09 (1H, s).
The active compound 51
¹ H-NMR (CDCl ₃ ) δ: 5.15 (2H, s), 6.74 (2H, brs), 7.37 (1H, d), 7.60 (1H, s), 8.64 ( 1H, d).
The active compound 52
¹ H-NMR (CDCl ₃ ) δ: 2.93 (2H, t), 4.64 (2H, t), 5.54-5.56 (1H, m), 5.72-5.74 (1H M), 7.22-7.24 (1H, m), 8.12 (1H, s), 8.66 (1H, s), 9.18 (1H, s).
The active compound 53
¹ H-NMR (CDCl ₃ ) δ: 2.92 (2H, t), 4.64 (2H, t), 5.56 (1H, d), 5.73 (1H, d), 6.67 ( 1H, d), 7.21 (1H, s), 7.59-7.61 (1H, m), 8.41 (1H, s), 8.66 (1H, d).
The active compound 54
¹ H-NMR (CDCl ₃ ) δ: 4.89-4.95 (2H, m), 5.05-5.22 (1H, m), 8.24 (1H, s), 8.51 (1H , S), 9.12 (1H, s).
The active compound 55
¹ H-NMR (CDCl ₃ ) δ: 5.23 (2H, s), 8.24 (1H, s), 8.50 (1H, s), 9.12 (1H, s).
The active compound 56
¹ H-NMR (CDCl ₃ ) δ: 2.23 (3H, s), 4.86 (2H, s), 7.36 (1H, s), 8.13 (1H, s), 8.67 ( 1H, s), 9.19 (1H, s).
The active compound 57
¹ H-NMR (CDCl ₃ ) δ: 2.23 (3H, s), 4.85 (2H, s), 6.81 (1H, d), 7.21-7.24 (1H, m), 7.61-7.64 (1H, m), 8.43-8.45 (1H, m), 8.67 (1H, d).
The active compound 58
¹ H-NMR (CDCl ₃ ) δ: 4.78-4.91 (2H, m), 4.99-5.21 (1H, m), 6.66 (2H, brs), 7.29 (1H , D), 7.60 (1H, s), 8.65 (1H, d).
The active compound 59
¹ H-NMR (DMSO-D ₆ ) δ: 1.50 (3H, d), 5.80-5.94 (1H, m), 6.62-6.93 (1H, m), 7.32 (1H, d), 8.42 (1H, s), 8.89 (1H, d), 9.49 (1H, s).
The active compound 60
¹ H-NMR (CDCl ₃ ) δ: 4.88-5.15 (3H, m), 5.53 (2H, brs), 8.09 (1H, s), 8.17 (1H, s), 9.23 (1H, s).

The active compound 61
¹ H-NMR (CDCl ₃ ) δ: 4.91-5.07 (3H, m), 8.17 (1H, s), 8.76 (1H, s), 9.22 (1H, s).
The active compound 62
¹ H-NMR (CDCl ₃ ) δ: 2.54 (3H, d), 4.84-4.91 (2H, m), 4.99-5.16 (1H, m), 8.15 (1H , S), 8.56 (1H, d), 9.11 (1H, s).
The active compound 63
¹ H-NMR (CDCl ₃ ) δ: 2.53 (3H, s), 4.87-4.90 (2H, m), 6.00 (1H, tt), 8.15 (1H, s), 8.56 (1H, s), 9.10 (1H, s).
The active compound 64
¹ H-NMR (CDCl ₃ ) δ: 2.60 (3H, d), 5.15 (2H, s), 8.15 (1H, s), 8.55 (1H, d), 9.11 ( 1H, s).
The active compound 65
¹ H-NMR (CDCl ₃ ) δ: 1.70 (6H, s), 4.53 (2H, s), 7.31 (1H, d), 8.13 (1H, s), 8.65 ( 1H, d), 9.19 (1H, s).
The active compound 66
¹ H-NMR (CDCl ₃ ) δ: 4.80-4.91 (2H, m), 5.00-5.20 (1H, m), 6.39 (2H, brs), 6.67 (1H , S), 6.75 (1H, d), 6.88 (1H, d), 8.66 (1H, s).
The active compound 67
¹ H-NMR (CDCl ₃ ) δ: 4.87 (2H, tt), 5.98 (1H, tt), 6.28 (2H, brs), 6.67 (1H, d), 6.75 ( 1H, d), 6.89 (1H, d), 8.65 (1H, d).
The active compound 68
¹ H-NMR (CDCl ₃ ) δ: 4.83-4.94 (2H, m), 5.00-5.20 (1H, m), 7.37 (1H, s), 8.06 (1H , S), 8.81 (1H, s).
The active compound 69
¹ H-NMR (CDCl ₃ ) δ: 4.82-4.99 (2H, m), 5.09-5.26 (1H, m), 8.21 (1H, s), 8.64 (1H , S), 9.06 (1H, s).
The active compound 70
¹ H-NMR (CDCl ₃ ) δ: 4.90-4.96 (2H, m), 6.08 (1H, tt), 8.21 (1H, s), 8.64 (1H, s), 9.05 (1H, s).
The active compound 71
¹ H-NMR (CDCl ₃ ) δ: 5.21 (2H, s), 8.22 (1H, s), 8.63 (1H, s), 9.05 (1H, s).
The active compound 72
¹ H-NMR (CDCl ₃ ) δ: 1.54-1.59 (3H, m), 4.94-5.22 (1H, m), 5.75-5.89 (1H, m), 7 .31 (1H, d), 8.13 (1H, s), 8.68 (1H, d), 9.19 (1H, s).
The active compound 73
¹ H-NMR (CDCl ₃ ) δ: 1.56 (3H, t), 4.93-5.21 (1H, m), 5.76-5.89 (1H, m), 6.73-6 .76 (1H, m), 7.22-7.24 (1H, m), 7.60-7.62 (1H, m), 8.44 (1H, s), 8.67-8.69 (1H, m).
The active compound 74
¹ H-NMR (CDCl ₃ ) δ: 0.96 (9H, s), 3.21 (2H, d), 4.83-5.16 (3H, m), 6.96 (1H, s), 8.08 (1H, s), 8.17 (1H, s), 9.23 (1H, s).
The active compound 75
¹ H-NMR (CDCl ₃ ) δ: 5.00 (2H, t), 7.39 (1H, s), 8.14 (1H, s), 8.68 (1H, s), 9.20 ( 1H, s).
The active compound 76
¹ H-NMR (CDCl ₃ ) δ: 5.04 (2H, t), 7.39 (1H, s), 8.13 (1H, s), 8.68 (1H, s), 9.20 ( 1H, s).
The active compound 77
¹ H-NMR (CDCl ₃ ) δ: 1.25 (3H, t), 3.06 (2H, q), 4.84-4.92 (2H, m), 5.01-5.12 (1H M), 8.15 (1H, s), 8.56 (1H, s), 9.12 (1H, s).
The active compound 78
¹ H-NMR (CDCl ₃ ) δ: 1.24 (3H, t), 3.05 (2H, q), 4.88-4.91 (2H, m), 5.99 (1H, tt), 8.14 (1H, s), 8.56 (1H, s), 9.11 (1H, s).
The active compound 79
¹ H-NMR (CDCl ₃ ) δ: 1.31 (3H, t), 3.11 (2H, q), 5.16 (2H, s), 8.15 (1H, s), 8.55 ( 1H, s), 9.11 (1H, s).
The active compound 80
¹ H-NMR (CDCl ₃ ) δ: 4.83-4.97 (2H, m), 6.05 (1H, t), 7.33 (1H, s), 8.13 (1H, s), 8.66 (1H, s), 9.19 (1H, s).

The active compound 81
¹ H-NMR (CDCl ₃ ) δ: 1.60 (3H, s), 4.81 (2H, s), 8.21 (1H, s), 8.61 (1H, s), 9.07 ( 1H, s).
The active compound 82
¹ H-NMR (CDCl ₃ ) δ: 5.08 (2H, t), 6.10 (1H, tt), 8.22 (1H, s), 8.63 (1H, s), 9.09 ( 1H, s).
The active compound 83
¹ H-NMR (CDCl ₃ ) δ: 1.62 (3H, d), 5.77-6.20 (2H, m), 8.21 (1H, s), 8.61 (1H, s), 9.07 (1H, s).
The active compound 84
¹ H-NMR (CDCl ₃ ) δ: 1.61-1.66 (3H, m), 4.98-5.30 (1H, m), 5.70-5.86 (1H, m), 8 .22 (1H, s), 8.61-8.62 (1H, m), 9.08 (1H, s).
The active compound 85
¹ H-NMR (CDCl ₃ ) δ: 1.35 (6H, d), 3.78-3.85 (1H, m), 4.88-5.16 (3H, m), 8.14 (1H , S), 8.56 (1H, s), 8.91 (1H, s).
The active compound 86
¹ H-NMR (CDCl ₃ ) δ: 1.35 (6H, d), 3.74-3.81 (1H, m), 4.89-4.92 (2H, m), 6.00 (1H , Tt), 8.13 (1H, s), 8.56 (1H, s), 8.89 (1H, s).
The active compound 87
¹ H-NMR (CDCl ₃ ) δ: 0.17 (9H, s), 4.25 (2H, s), 8.20 (1H, s), 8.58 (1H, s), 9.02 ( 1H, s).
The active compound 88
¹ H-NMR (CDCl ₃ ) δ: 0.12 (9H, s), 1.22-1.28 (2H, m), 4.62-4.69 (2H, m), 8.20 (1H , S), 8.58 (1H, s), 9.02 (1H, s).
The active compound 89
¹ H-NMR (CDCl ₃ ) δ: 1.25 (9H, s), 4.88-5.14 (3H, m), 8.11 (1H, s), 8.52 (1H, s), 8.53 (1H, s).
The active compound 90
¹ H-NMR (CDCl ₃ ) δ: 1.24 (9H, s), 4.89-4.93 (2H, m), 5.99 (1H, tt), 8.11 (1H, s), 8.51 (1H, s), 8.53 (1H, s).
The active compound 91
¹ H-NMR (CDCl ₃ ) δ: 1.57 (3H, s), 2.51 (3H, d), 4.90-5.18 (1H, m), 5.77-5.89 (1H M), 8.15 (1H, s), 8.55 (1H, d), 9.10 (1H, d).
The active compound 92
¹ H-NMR (CDCl ₃ ) δ: 1.56 (3H, s), 2.49-2.51 (3H, m), 5.80-6.12 (2H, m), 8.14 (1H , S), 8.55 (1H, s), 9.09 (1H, s).
The active compound 93
¹ H-NMR (CDCl ₃ ) δ: 2.54 (3H, s), 5.01 (2H, t), 6.09 (1H, tt), 8.15 (1H, s), 8.56 ( 1H, s), 9.11 (1H, s).
The active compound 94
¹ H-NMR (CDCl ₃ ) δ: 1.55 (3H, s), 2.50 (3H, s), 4.74 (2H, s), 8.14 (1H, s), 8.55 ( 1H, s), 9.09 (1H, s).
The active compound 95
¹ H-NMR (CDCl ₃ ) δ: 0.16 (9H, s), 2.45 (3H, s), 4.15 (2H, s), 8.13 (1H, s), 8.53 ( 1H, s), 9.03 (1H, s).
The active compound 96
¹ H-NMR (CDCl ₃ ) δ: 0.10 (9H, s), 1.15 to 1.23 (2H, m), 2.45 (3H, s), 4.52 to 4.58 (2H) M), 8.13 (1H, s), 8.52 (1H, s), 9.03 (1H, s).
The active compound 97
¹ H-NMR (CDCl ₃ ) δ: 1.79 (3H, d), 6.10 (1H, q), 8.22 (1H, s), 8.62 (1H, s), 9.08 ( 1H, s).
The active compound 98
¹ H-NMR (CDCl ₃ ) δ: 2.29 (3H, s), 4.92 (2H, s), 8.22 (1H, s), 8.61 (1H, s), 9.08 ( 1H, s).
The active compound 99
¹ H-NMR (CDCl ₃ ) δ: 1.75 (3H, d), 2.54 (3H, s), 6.06 (1H, q), 8.15 (1H, s), 8.55 ( 1H, s), 9.09 (1H, s).
The active compound 100
¹ H-NMR (CDCl ₃ ) δ: 2.25 (3H, s), 2.56 (3H, s), 4.84 (2H, s), 8.15 (1H, s), 8.54 ( 1H, s), 9.09 (1H, s).

The active compound 101
¹ H-NMR (CDCl ₃ ) δ: 5.08 (2H, t), 8.22 (1H, s), 8.63 (1H, s), 9.09 (1H, s).
The active compound 102
¹ H-NMR (CDCl ₃ ) δ: 2.54 (3H, s), 5.00 (2H, t), 8.15 (1H, s), 8.56 (1H, s), 9.11 ( 1H, s).
The active compound 103
¹ H-NMR (CDCl ₃ ) δ: 5.02 (2H, t), 7.38 (1H, s), 8.14 (1H, s), 8.69 (1H, s), 9.20 ( 1H, s).
The active compound 104
¹ H-NMR (CDCl ₃ ) δ: 2.12-2.21 (2H, m), 2.28-2.42 (2H, m), 4.61 (2H, t), 8.21 (1H , S), 8.59 (1H, s), 9.05 (1H, s).
The active compound 105
¹ H-NMR (CDCl ₃ ) δ: 2.08-2.18 (2H, m), 2.25-2.38 (2H, m), 2.48 (3H, s), 4.53 (2H , T), 8.14 (1H, s), 8.53 (1H, s), 9.06 (1H, s).
The active compound 106
¹ H-NMR (CDCl ₃ ) δ: 2.05-2.14 (2H, m), 2.23-2.37 (2H, m), 4.51 (2H, t), 7.23 (1H , S), 8.12 (1H, s), 8.65 (1H, s), 9.18 (1H, s).
The active compound 107
¹ H-NMR (CDCl ₃ ) δ: 3.99 (3H, s), 4.91-4.98 (2H, m), 5.04-5.15 (1H, m), 8.20 (1H , S), 8.50 (1H, s), 9.09 (1H, s).
The active compound 108
¹ H-NMR (CDCl ₃ ) δ: 4.00 (3H, s), 4.92-4.99 (2H, m), 6.01 (1H, tt), 8.20 (1H, s), 8.50 (1H, s), 9.09 (1H, s).
The active compound 109
¹ H-NMR (CDCl ₃ ) δ: 1.74 (6H, s), 4.59 (2H, s), 8.21 (1H, s), 8.59 (1H, s), 9.06 ( 1H, s).
The active compound 110
¹ H-NMR (CDCl ₃ ) δ: 1.72 (6H, s), 2.54 (3H, s), 4.52 (2H, s), 8.14 (1H, s), 8.53 ( 1H, s), 9.07 (1H, s).
The active compound 111
¹ H-NMR (CDCl ₃ ) δ: 5.03 (2H, t), 7.38 (1H, d), 8.14 (1H, s), 8.69 (1H, d), 9.20 ( 1H, s).
The active compound 112
¹ H-NMR (CDCl ₃ ) δ: 5.03 (2H, t), 7.38 (1H, s), 8.14 (1H, s), 8.69 (1H, s), 9.20 ( 1H, s).
The active compound 113
¹ H-NMR (CDCl ₃ ) δ: 4.47-4.58 (1H, m), 4.71-4.87 (2H, m), 7.17-7.19 (2H, m), 7 .43-7.45 (3H, m), 7.90 (1H, s), 8.61 (1H, s), 8.77 (1H, s).
The active compound 114
¹ H-NMR (CDCl ₃ ) δ: 4.82-4.85 (2H, m), 5.60 (1H, tt), 7.16-7.20 (2H, m), 7.41-7 .44 (3H, m), 7.90 (1H, s), 8.54 (1H, s), 8.77 (1H, s).
The active compound 115
¹ H-NMR (CDCl ₃ ) δ: 4.91-5.05 (2H, m), 5.14-5.25 (1H, m), 8.29 (1H, s), 8.82 (1H , S), 9.27 (1H, s).
The active compound 116
¹ H-NMR (CDCl ₃ ) δ: 4.99-5.02 (2H, m), 6.09 (1H, tt), 8.28 (1H, s), 8.81 (1H, s), 9.26 (1H, s).
The active compound 117
¹ H-NMR (CDCl ₃ ) δ: 2.33 (3H, d), 4.85-4.92 (2H, m), 5.01-5.12 (1H, m), 7.22-7 .23 (1H, m), 7.47-7.48 (1H, m), 8.07-8.08 (1H, m), 8.60 (1H, d).
The active compound 118
¹ H-NMR (CDCl ₃ ) δ: 2.33 (3H, d), 4.86-4.93 (2H, m), 5.99 (1H, tt), 7.22-7.23 (1H M), 7.46-7.47 (1H, m), 8.07-8.08 (1H, m), 8.60 (1H, d).
The active compound 119
¹ H-NMR (CDCl ₃ ) δ: 4.82-4.99 (2H, m), 5.03-5.26 (1H, m), 7.22 (1H, s), 7.87-7 .88 (1H, m), 8.53 (1H, s), 8.59 (1H, s).
The active compound 120
¹ H-NMR (CDCl ₃ ) δ: 4.91-4.94 (2H, m), 6.05 (1H, tt), 7.21-7.22 (1H, m), 7.86-7 .87 (1H, m), 8.52-8.53 (1H, m), 8.59 (1H, s).

The active compound 121
¹ H-NMR (CDCl ₃ ) δ: 2.53-2.68 (2H, m), 3.45-3.51 (2H, m), 7.73 (1H, d), 8.13 (1H , S), 8.83 (1H, d), 9.20 (1H, s).
The active compound 122
¹ H-NMR (CDCl ₃ ) δ: 2.53-2.68 (2H, m), 3.46-3.52 (2H, m), 8.21 (1H, s), 8.80 (1H , S), 9.08 (1H, s).
The active compound 123
¹ H-NMR (CDCl ₃ ) δ: 2.53-2.68 (5H, m), 3.46-3.52 (2H, m), 8.14 (1H, s), 8.74 (1H , S), 9.08 (1H, s).
The active compound 124
¹ H-NMR (CDCl ₃ ) δ: 1.91 (6H, s), 4.66 (2H, s), 8.21 (1H, s), 8.58-8.60 (1H, m), 9.05 (1H, s).
The active compound 125
¹ H-NMR (CDCl ₃ ) δ: 1.82 (3H, t), 4.70 (2H, t), 8.21 (1H, s), 8.61 (1H, s), 9.07 ( 1H, s).
The active compound 126
¹ H-NMR (CDCl ₃ ) δ: 5.06 (2H, t), 6.14 (1H, tt), 8.22 (1H, s), 8.63 (1H, s), 9.09 ( 1H, s).
The active compound 127
¹ H-NMR (CDCl ₃ ) δ: 1.76 (3H, t), 4.64 (2H, t), 7.33-7.35 (1H, m), 8.13 (1H, s), 8.67 (1H, s), 9.19 (1H, s).
The active compound 128
¹ H-NMR (CDCl ₃ ) δ: 5.00 (2H, t), 6.09 (1H, tt), 7.38 (1H, s), 8.14 (1H, s), 8.69 ( 1H, s), 9.20 (1H, s).
The active compound 129
¹ H-NMR (CDCl ₃ ) δ: 1.78 (3H, t), 2.53 (3H, s), 4.63 (2H, t), 8.14 (1H, s), 8.54 ( 1H, s), 9.09 (1H, s).
The active compound 130
¹ H-NMR (CDCl ₃ ) δ: 2.54 (3H, s), 4.99 (2H, t), 6.09 (1H, tt), 8.15 (1H, s), 8.56 ( 1H, s), 9.10 (1H, s).
The active compound 131
¹ H-NMR (CDCl ₃ ) δ: 4.80-4.97 (2H, m), 5.06-5.27 (1H, m), 6.29 (2H, brs), 7.67 (1H , S), 8.55 (1H, s).
The active compound 132
¹ H-NMR (CDCl ₃ ) δ: 2.54 (3H, s), 4.80-4.90 (2H, m), 4.96-5.18 (1H, m), 6.33 (2H , Brs), 7.60 (1H, s), 8.52 (1H, s).
The active compound 133
¹ H-NMR (CDCl ₃ ) δ: 4.08-4.17 (2H, m), 4.90-5.10 (1H, m), 7.81 (1H, d), 8.14 (1H , S), 8.84 (1H, d), 9.21 (1H, s).
The active compound 134
¹ H-NMR (CDCl ₃ ) δ: 0.16 (9H, s), 2.25 (3H, s), 4.14 (2H, s), 7.21-7.21 (1H, m), 7.43-7.43 (1H, m), 8.03-8.03 (1H, m), 8.57 (1H, s).
The active compound 135
¹ H-NMR (CDCl ₃ ) δ: 0.11 (9H, s), 1.17-1.21 (2H, m), 2.25 (3H, s), 4.53-4.58 (2H M), 7.21 (1H, s), 7.44 (1H, s), 8.03 (1H, s), 8.55 (1H, s).
The active compound 136
¹ H-NMR (CDCl ₃ ) δ: 2.64 (3H, s), 4.08-4.26 (2H, m), 4.89-5.09 (1H, m), 8.15 (1H , S), 8.74 (1H, s), 9.10 (1H, s).
The active compound 137
¹ H-NMR (CDCl ₃ ) δ: 2.63 (3H, s), 4.06 to 4.15 (2H, m), 5.90 (1H, tt), 8.15 (1H, s), 8.74 (1H, s), 9.09 (1H, s).
The active compound 138
¹ H-NMR (CDCl ₃ ) δ: 5.08-5.15 (2H, m), 5.95-6.07 (1H, m), 6.53-6.63 (1H, m), 7 .31 (1H, s), 8.13 (1H, s), 8.67 (1H, s), 9.19 (1H, s).
The active compound 139
¹ H-NMR (CDCl ₃ ) δ: 2.54 (3H, s), 5.08-5.15 (2H, m), 5.94-6.07 (1H, m), 6.55-6 .67 (1H, m), 8.15 (1H, s), 8.54 (1H, s), 9.09 (1H, s).
The active compound 140
¹ H-NMR (CDCl ₃ ) δ: 1.04 (3H, t), 1.57 (1H, dt), 1.68-1.80 (1H, m), 1.91-2.02 (1H M), 2.07-2.18 (1H, m), 2.19-2.32 (1H, m), 4.53 (2H, t), 7.22 (1H, s), 8. 12 (1H, s), 8.65 (1H, s), 9.18 (1H, s).

The active compound 141
¹ H-NMR (CDCl ₃ ) δ: 1.05 (3H, t), 1.52-1.64 (1H, m), 1.70-1.83 (1H, m), 1.93-2 .04 (1H, m), 2.10-2.33 (2H, m), 2.47 (3H, s), 4.55 (2H, t), 8.13 (1H, s), 8. 53 (1H, s), 9.06 (1H, s).
The active compound 142
¹ H-NMR (CDCl ₃ ) δ: 2.53 (3H, s), 4.84 (2H, d), 6.09 (1H, t), 8.14 (1H, s), 8.53 ( 1H, s), 9.09 (1H, s).
The active compound 143
¹ H-NMR (CDCl ₃ ) δ: 2.55 (3H, s), 4.89 (2H, q), 8.15 (1H, s), 8.55 (1H, s), 9.10 ( 1H, s).
The active compound 144
¹ H-NMR (CDCl ₃ ) δ: 2.52 (3H, s), 4.72 (2H, dd), 4.84 (2H, dd), 5.65-5.82 (1H, m), 8.14 (1H, s), 8.53 (1H, s), 9.07 (1H, s).
The active compound 145
¹ H-NMR (CDCl ₃ ) δ: 1.56-1.62 (3H, m), 2.50 (3H, s), 5.90-6.03 (1H, m), 8.14 (1H , S), 8.54 (1H, s), 9.09 (1H, s).
The active compound 146
¹ H-NMR (CDCl ₃ ) δ: 1.71-1.82 (2H, m), 1.88-1.98 (2H, m), 2.12-2.26 (2H, m), 2 .47 (3H, s), 4.49 (2H, t), 8.13 (1H, s), 8.52 (1H, s), 9.05 (1H, s).
The active compound 147
¹ H-NMR (CDCl ₃ ) δ: 2.48 (3H, s), 2.62-2.75 (2H, m), 4.70 (2H, t), 8.13 (1H, s), 8.54 (1H, s), 9.07 (1H, s).
The active compound 148
¹ H-NMR (CDCl ₃ ) δ: 1.69-1.82 (2H, m), 1.86-1.96 (2H, m), 2.12-2.26 (2H, m), 4 .47 (2H, t), 7.22 (1H, s), 8.12 (1H, s), 8.64 (1H, s), 9.18 (1H, s).
The active compound 149
¹ H-NMR (CDCl ₃ ) δ: 2.69 (3H, s), 8.16 (1H, s), 8.76 (1H, s), 9.16 (1H, s).
The active compound 150
¹ H-NMR (CDCl ₃ ) δ: 2.54 (3H, s), 2.89-3.09 (2H, m), 4.75 (2H, t), 8.15 (1H, s), 8.56 (1H, s), 9.11 (1H, s).
The active compound 151
¹ H-NMR (CDCl ₃ ) δ: 2.45-2.57 (3H, m), 4.53-5.37 (4H, m), 8.15 (1H, brs), 8.55 (1H , Brs), 9.04-9.14 (1H, m).
The active compound 152
¹ H-NMR (CDCl ₃ ) δ: 1.11 (3H, t), 1.96-2.16 (2H, m), 2.53 (3H, s), 4.65 (2H, t), 8.15 (1H, s), 8.54 (1H, s), 9.09 (1H, s).
The active compound 153
¹ H-NMR (CDCl ₃ ) δ: 1.24 (3H, t), 2.36 (2H, q), 4.89 (2H, s), 7.35 (1H, s), 8.12 ( 1H, s), 8.67 (1H, s), 9.19 (1H, s).
The active compound 154
¹ H-NMR (CDCl ₃ ) δ: 1.25 (3H, t), 2.37 (2H, q), 2.54 (3H, s), 4.87 (2H, s), 8.15 ( 1H, s), 8.54 (1H, s), 9.09 (1H, s).
The active compound 155
¹ H-NMR (CDCl ₃ ) δ: 1.26 (3H, t), 2.42 (2H, q), 4.95 (2H, s), 8.21 (1H, s), 8.61 ( 1H, s), 9.07 (1H, s).
The active compound 156
¹ H-NMR (CDCl ₃ ) δ: 1.22 (6H, d), 2.53-2.55 (3H, m), 2.59-2.68 (1H, m), 4.90 (2H , S), 8.15 (1H, s), 8.54 (1H, s), 9.09 (1H, s).
The active compound 157
¹ H-NMR (CDCl ₃ ) δ: 1.23 (6H, d), 2.67-2.74 (1H, m), 4.99 (2H, s), 8.21 (1H, s), 8.61 (1H, s), 9.07 (1H, s).
The active compound 158
¹ H-NMR (CDCl ₃ ) δ: 1.21 (6H, d), 2.57-2.67 (1H, m), 4.92 (2H, s), 7.34 (1H, s), 8.13 (1H, s), 8.67 (1H, s), 9.19 (1H, s).

Next, formulation examples are shown. In the following examples, parts represent parts by weight unless otherwise specified.
Formulation Example 1
1 part of the compound of any one of the present active compounds 1 to 158 described above and 9 parts of any one organic phosphorus compound selected from the group consisting of chlorpyrifos, chlorpyrifosmethyl, acephate, methamidophos, methidathion and fenitrothion, Dissolve in a mixture of 35 parts of xylene and 35 parts of N, N-dimethylformamide, add 14 parts of polyoxyethylene styryl phenyl ether and 6 parts of calcium dodecylbenzenesulfonate and mix well to obtain 10% emulsions. .

Formulation Example 2
4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, 20 parts of synthetic silicon hydroxide fine powder and 54 parts of diatomaceous earth are mixed, and 5 parts of any one of the above active compounds 1 to 158 are mixed with chlorpyrifos. And 15 parts of an organophosphorus compound selected from the group consisting of chloropyrifosmethyl, acephate, methamidophos, methidathion, and fenitrothion, and mixed well to obtain each 20% wettable powder.

Formulation Example 3
1 part of any one of the active compounds 1 to 158 described above and 1 part of an organophosphorus compound selected from the group consisting of chlorpyrifos, chlorpyrifosmethyl, acephate, methamidophos, methidathion, and fenitrothion, Add 1 part of synthetic hydrous hydrous powder, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65 parts of kaolin clay and mix well. Next, an appropriate amount of water is added to these mixtures, and the mixture is further stirred, granulated with a granulator, and dried by ventilation to obtain 2% granules.

Formulation Example 4
0.9 part of any one of the above active compounds 1 to 158 described above, and any one organophosphorus compound selected from the group consisting of chlorpyrifos, chlorpyrifosmethyl, acephate, methamidophos, methidathion and fenitrothion 0.1 Are dissolved in an appropriate amount of acetone, and 5 parts of synthetic silicon hydroxide fine powder, 0.3 part of PAP (isopropyl acid phosphate) and 93.7 parts of fusami clay are added, and the mixture is thoroughly stirred and mixed. Evaporate off to obtain each 1% powder.

Formulation Example 5
35 parts of a mixture of polyoxyethylene alkyl ether sulfate ammonium salt and white carbon (1: 1 by weight), 8 parts of any one of the above active compounds 1-158, chlorpyrifos, chloropyrifosmethyl, acephate, 10 parts of each flowable agent is obtained by mixing 2 parts of any one organic phosphorus compound selected from the group consisting of methamidophos, methidathion and fenitrothion and 55 parts of water and finely pulverizing them by a wet pulverization method.

Formulation Example 6
0.06 part of any one of the above-mentioned active compounds 1 to 158 described above and 0.06 part of any one of the organic phosphorus compounds selected from the group consisting of chlorpyrifos, chlorpyrifosmethyl, acephate, methamidophos, methidathion and fenitrothion 0.06 Are dissolved in 5 parts of xylene and 5 parts of trichloroethane, and this is mixed with 89.9 parts of deodorized kerosene to obtain each 0.1% oil.

Formulation Example 7
7 mg of any one of the above-mentioned active compounds 1 to 158 and 3 mg of any one organophosphorus compound selected from the group consisting of chlorpyrifos, chlorpyrifosmethyl, acephate, methamidophos, methidathion and fenitrothion are mixed with acetone 0 Dissolve in 5 ml, and treat this solution to 5 g of animal solid feed powder (solid feed powder CE-2 for breeding, product of Nippon Claire Co., Ltd.) and mix uniformly. Then, acetone is evaporated to dryness to obtain each poisonous bait.

Formulation Example 8
0.07 part of any one of the above active compounds 1 to 158 described above, 0.07 part of any one of the organic phosphorus compounds selected from the group consisting of chlorpyrifos, chlorpyrifosmethyl, acephate, methamidophos, methidathion and fenitrothion , Put 49.9 parts of Neothiozole (Chuo Kasei Co., Ltd.) into an aerosol can, attach an aerosol valve, fill 25 parts of dimethyl ether and 25 parts of LPG, shake, and install an actuator to obtain an oil aerosol .

Formulation Example 9
0.5 part of any one of the above active compounds 1 to 158 described above, 0.1 part of any one organic phosphorus compound selected from the group consisting of chlorpyrifos, chlorpyrifosmethyl, acephate, methamidophos, methidathion and fenitrothion , 0.01 part of BHT (2,6-di-tert-butyl-4-methylphenol), 5 parts of xylene, 3.39 parts of deodorized kerosene and 1 part of an emulsifier {Atmos 300 (registered trademark name of Atmos Chemical)} After mixing and dissolving, 50 parts of distilled water is filled in an aerosol container, and a valve is attached. Then, 40 parts of a propellant (LPG) is pressurized and filled through the valve to obtain an aqueous aerosol.

Formulation Example 10
2 parts of any one of the above active compounds 1 to 158, 8 parts of any one of the organic phosphorus compounds selected from the group consisting of chlorpyrifos, chlorpyrifosmethyl, acephate, methamidophos, methidathion, and fenitrothion; Pesticides such as insecticides, acaricides, nematicides or fungicides, plant hormones, plant growth regulators, herbicides, etc. that can be formulated with active compounds and organophosphorus compounds (isomers) And 10 parts of a synergist or safener, and a mixture of 4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, 20 parts of synthetic silicon hydroxide fine powder and 54 parts of diatomaceous earth, Stir and mix well to obtain a mixed wettable powder.

Next, the control effect with respect to harmful animals of the composition of the present invention is shown by test examples.
Test Example 1 (Insecticidal effect by spraying leaves on Aphis gossypii)
The active compounds 12, 27, 48, 49, 62, 63, 82, 93 and 100 were formulated as the active compounds by the method of Preparation Example 5 and diluted to a predetermined concentration. In addition, a commercially available chlorpyrifos wettable powder (trade name: Darzvan wettable powder; manufactured by Nissan Chemical Co., Ltd.) is used as the organic phosphorus compound. Dilute to concentration. Each diluted solution of this active compound and a diluted solution of chlorpyrifos were mixed so as to have a predetermined concentration to obtain a test drug solution.
On the day before the test, a total of about 30 cotton aphid larvae and adults were released on cucumber seedlings (2 weeks after sowing, the second leaf development stage. The first true leaf was left and the second true leaf was excised). On the next day, 20 ml of the test drug solution was sprayed on the seedlings. After the chemical solution sprayed on the cucumber was dried, the seedling was put in a polyethylene cup and covered with a lid having five air holes having a diameter of about 5 mm. After storing in a greenhouse at 25 ° C., the number of surviving insects was examined after 6 days. The control value (%) was calculated by the following formula, and the results are shown in Table 9.
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 shown in Table 9, the composition comprising each of the present active compounds 12, 27, 48, 49, 62, 63, 82, 93 and 100 and chlorpyrifos showed a high control effect against cotton aphids.

  ADVANTAGE OF THE INVENTION According to this invention, the pest control composition which has high activity, and the method which can control a pest animal effectively can be provided.

Claims (24)

Formula (1)

[Where,
Q represents oxygen or sulfur,
G ¹ represents nitrogen or CH,
R ¹ represents hydrogen or an amino group,
R ² is hydrogen, halogen, nitro group, amino group, cyano group, C1-C6 chain hydrocarbon group optionally substituted with halogen, C3-C6 cycloalkyl group optionally substituted with halogen, halogen, A C1-C6 alkoxy group which may be substituted, a C1-C4 alkylamino group which may be substituted with a halogen, or a C2-C8 dialkylamino group which may be substituted with a halogen,
R ³ represents a C1-C6 alkyl group substituted with one or more groups selected from group A or a C3-C6 alkenyl group substituted with one or more groups selected from group A;
Group A is a halogen and -Si (R ⁴⁾ ₃
{R ⁴ may be the same or different from each other, and represents a C1-C6 chain hydrocarbon group which may be substituted with halogen. } Represents a group consisting of. ]
And a pesticide composition comprising at least one organic phosphorus compound selected from the group consisting of chlorpyrifos, chlorpyrifosmethyl, acephate, methamidophos, methidathion and fenitrothion.   The pest control composition according to claim 1, wherein Q in the formula (1) is oxygen. The pest control composition according to claim 1 or 2, wherein R ² in formula (1) is hydrogen, halogen or a C1-C6 alkyl group optionally substituted with halogen. The pest control composition according to claim 1 or 2, wherein R ² in formula (1) is a C1-C6 alkyl group optionally substituted with hydrogen or halogen. The pest control composition according to any one of claims 1 to 4, wherein R ¹ in formula (1) is hydrogen. In formula (1), R ³ is pest control composition according one wherein any one of claims 1 to 5 is a C3-C6 alkenyl group substituted with C1-C6 alkyl group or a halogen substituted with halogen. In formula (1), R ³ is pest control composition of claims 1 to 5 any one claim is a C1-C6 alkyl group substituted with halogen. The pest control composition according to any one of claims 1 to 5, wherein R ³ in the formula (1) is a C1-C6 alkyl group substituted with 1 to 8 fluorine or chlorine. In the formula (1), pest control composition of claims 1 to 8 to any one claim G ¹ is a nitrogen.   The harmful animal pest control composition according to any one of claims 1 to 9, wherein the weight ratio of the pyrimidine compound and the organophosphorus compound is 5:95 to 95: 5. Formula (A)

[Where,
R ^2A represents hydrogen, C1-C3 alkyl or halogen;
R ^3A represents a C1-C6 alkyl group which may be substituted with halogen or a C3-C6 alkenyl group which may be substituted with halogen. ]
And a pesticide composition comprising at least one organic phosphorus compound selected from the group consisting of chlorpyrifos, chlorpyrifosmethyl, acephate, methamidophos, methidathion and fenitrothion.   The harmful animal pest control composition according to claim 11, wherein the weight ratio of the pyrimidine compound and the organophosphorus compound is 5:95 to 95: 5. Formula (1)

[Where,
Q represents oxygen or sulfur,
G ¹ represents nitrogen or CH,
R ¹ represents hydrogen or an amino group,
R ² is hydrogen, halogen, nitro group, amino group, cyano group, C1-C6 chain hydrocarbon group optionally substituted with halogen, C3-C6 cycloalkyl group optionally substituted with halogen, halogen, A C1-C6 alkoxy group which may be substituted, a C1-C4 alkylamino group which may be substituted with a halogen, or a C2-C8 dialkylamino group which may be substituted with a halogen,
R ³ represents a C1-C6 alkyl group substituted with one or more groups selected from group A or a C3-C6 alkenyl group substituted with one or more groups selected from group A;
Group A is a halogen and -Si (R ⁴⁾ ₃
{R ⁴ may be the same or different from each other, and represents a C1-C6 chain hydrocarbon group which may be substituted with halogen. } Represents a group consisting of. ]
A harmful effect in which an effective amount of the pyrimidine compound represented by the above formula and at least one organophosphorus compound selected from the group consisting of chlorpyrifos, chlorpyrifosmethyl, acephate, methamidophos, methidathion and fenitrothion is applied to harmful animals or habitats of harmful animals Animal control methods.   The control method according to claim 13, wherein Q in the formula (1) is oxygen. The control method according to claim 13 or 14, wherein R ² in formula (1) is hydrogen, halogen or a C1-C6 alkyl group optionally substituted with halogen. The control method according to claim 13 or 14, wherein R ² in formula (1) is a C1-C6 alkyl group optionally substituted with hydrogen or halogen. In the formula (1), according to claim 13 to 16 The control method according to any one claim wherein R ¹ is hydrogen. In formula (1), R ³ is claim 13 to 17 The control method according to any one claim is a C3-C6 alkenyl group substituted with C1-C6 alkyl group or a halogen substituted with halogen. In the formula (1), according to claim 13 to 17 The control method according to any one claim wherein R ³ is C1-C6 alkyl group substituted with halogen. In formula (1), R ³ is one to eight fluorine or claim 13 to 17 The control method according to any one claim chlorine is C1-C6 alkyl group substituted with. In the formula (1), according to claim 13 to 20 The control method according to any one claim G ¹ is a nitrogen.   The control method according to any one of claims 13 to 21, wherein the weight ratio of the pyrimidine compound and the organophosphorus compound is 5:95 to 95: 5. Formula (A)

[Where,
R ^2A represents hydrogen, C1-C3 alkyl or halogen;
R ^3A represents a C1-C6 alkyl group which may be substituted with halogen or a C3-C6 alkenyl group which may be substituted with halogen. ]
A harmful effect in which an effective amount of the pyrimidine compound represented by the above formula and at least one organophosphorus compound selected from the group consisting of chlorpyrifos, chlorpyrifosmethyl, acephate, methamidophos, methidathion and fenitrothion is applied to harmful animals or habitats of harmful animals Animal control methods.   The control method according to claim 23, wherein the weight ratio of the pyrimidine compound and the organophosphorus compound is 5:95 to 95: 5.