JP2010265260A - Pyrimidine compound, and its use for pest control - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a new compound having control activity on a harmful organism. <P>SOLUTION: The pyrimidine compound is represented by formula (1) [in the formula, Q represents oxygen or -S(O)<SB>n</SB>-; n represents 0, 1 or 2; G<SP>1</SP>represents nitrogen or CR<SP>6</SP>; R<SP>1</SP>, R<SP>2</SP>and R<SP>6</SP>may be the same or different and each represents hydrogen, a halogen or the like; R<SP>3</SP>represents hydrogen, a halogen or the like; R<SP>4</SP>represents hydrogen, a halogen or the like; and R<SP>5</SP>represents a 1-10C alkyl group substituted at least with one group, or a 3-10C alkenyl group substituted at least with one group]. The compound has an excellent effect of controlling a harmful organism. <P>COPYRIGHT: (C)2011,JPO&INPIT

Description

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

  A compound having a pest control activity has been found and developed as an active ingredient of a pest control agent. Moreover, a certain kind of pyrimidine compound is known (for example, refer patent documents 1-5).

International Publication WO2006 / 072426 Pamphlet Japanese Unexamined Patent Publication No. Sho 63-039875 International publication WO99 / 41253 pamphlet International Publication WO2006 / 005571 Pamphlet International Publication WO2005 / 019207 Pamphlet

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

〔式中、
Ｑは酸素または−Ｓ（Ｏ）ｎ−を表し、
ｎは、０、１または２を表し、
Ｇ¹は窒素またはＣＲ⁶を表し、
Ｒ¹、Ｒ²およびＲ⁶は同一または相異なり、水素、ハロゲン、ニトロ基、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、−Ｌ¹Ｒ⁷、−Ｃ（＝Ｏ）Ｒ⁸、群Ａより選ばれる１個以上の基で置換されていてもよいフェニル基または群Ａより選ばれる１個以上の基で置換されていてもよい５員もしくは６員芳香へテロ環基を表し、
Ｌ¹は酸素、−Ｓ（Ｏ）ｎ−または−ＮＲ⁹−を表し、
Ｒ⁷は水素または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し（但し、Ｌ¹が−Ｓ（Ｏ）ｎ−であり、ｎが１または２である場合は、Ｒ⁷は水素ではない）、
Ｒ⁸は水素、ヒドロキシ基、アミノ基、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、
Ｒ⁹は水素、ハロゲンで置換されていてもよいＣ１−Ｃ６鎖状炭化水素基またはハロゲンで置換されていてもよいＣ１−Ｃ６アルキルスルホニル基を表し、
Ｒ³は水素、ハロゲン、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−Ｃ８シクロアルキル基または−Ｌ²Ｒ¹⁰を表し、
Ｒ⁴は水素、ハロゲン、ニトロ基、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−Ｃ８シクロアルキル基、−Ｌ²Ｒ¹⁰、−Ｃ（＝Ｏ）Ｒ¹¹、群Ａより選ばれる１個以上の基で置換されていてもよいフェニル基または群Ａより選ばれる１個以上の基で置換されていてもよい５−もしくは６−員芳香へテロ環基を表し、
Ｌ²は酸素、−Ｓ（Ｏ）ｎ−または−ＮＲ¹²−を表し、
Ｒ¹⁰は水素または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し（但し、Ｌ²が−Ｓ（Ｏ）ｎ−であり、ｎが１または２である場合は、Ｒ¹⁰は水素ではない）、
Ｒ¹¹は水素、ヒドロキシ基、アミノ基、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、
Ｒ¹²は水素、ハロゲンで置換されていてもよいＣ１−Ｃ６鎖状炭化水素基、またはハロゲンで置換されていてもよいＣ１−Ｃ６アルキルスルホニル基を表し、
Ｒ⁵は群Ｂより選ばれる１個以上の基で置換されたＣ１−Ｃ１０アルキル基または群Ｂより選ばれる１個以上の基で置換されたＣ３−Ｃ１０アルケニル基を表し、
群Ａはハロゲン、アミノ基、シアノ基、ニトロ基、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Ｃ１−Ｃ６アルコキシ基およびＳ（Ｏ）ｎＲ¹³（ここで、Ｒ¹³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）からなる群を表し、
群Ｂはハロゲン、−Ｌ³Ｒ¹⁴、及び−Ｃ（＝Ｏ）Ｒ¹⁵、
｛Ｌ³は酸素、−Ｓ（Ｏ）ｎ−、−ＮＲ¹⁶−または−Ｓｉ（Ｒ¹⁷）₂−を表し、
Ｒ¹⁴は水素、または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し（ここで、Ｌ³が−Ｓ（Ｏ）ｎ−であり、ｎが１または２である場合は、Ｒ¹⁴は水素ではない）、
Ｒ¹⁵は水素、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Ｃ１−Ｃ４アルキルアミノ基、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、またはハロゲンで置換されていてもよいＣ１−Ｃ６アルコキシ基を表し、
Ｒ¹⁶は水素、または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し、
Ｒ¹⁷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（以下、本発明化合物と記す。）。
［２］ Ｒ¹、Ｒ²およびＲ⁶が同一または相異なり、水素、ハロゲン、ニトロ基、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、−Ｌ¹Ｒ⁷または−Ｃ（＝Ｏ）Ｒ⁸である［１］記載のピリミジン化合物。
［３］ Ｒ¹、Ｒ²およびＲ⁶が同一または相異なり、水素、ハロゲン、ハロゲンで置換されていてもよいＣ１−Ｃ６鎖状炭化水素基、−Ｌ¹Ｒ⁷、または−Ｃ（＝Ｏ）Ｒ⁸である［１］または［２］記載のピリミジン化合物。
［４］ Ｒ¹およびＲ⁶が同一または相異なり、水素、ハロゲン、ハロゲンで置換されていてもよいＣ１−Ｃ６鎖状炭化水素基、または−Ｃ（＝Ｏ）Ｒ⁸である［１］〜［３］いずれか一項記載のピリミジン化合物。
［５］ Ｒ²が水素、ハロゲン、ハロゲンで置換されていてもよいＣ１−Ｃ６鎖状炭化水素基、または−Ｌ¹Ｒ⁷である［１］〜［４］いずれか一項記載のピリミジン化合物。
［６］ Ｒ⁴が水素、ハロゲン、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−Ｃ８シクロアルキル基、または−Ｌ²Ｒ¹⁰である［１］〜［５］いずれか一項記載のピリミジン化合物。
［７］ Ｒ³が水素、ハロゲン、ハロゲンで置換されていてもよいＣ１−Ｃ６鎖状炭化水素基、またはハロゲンで置換されていてもよいＣ３−Ｃ８シクロアルキル基である［１］〜［６］いずれか一項記載のピリミジン化合物。
［８］ Ｒ³が水素である［１］〜［６］いずれか一項記載のピリミジン化合物。
［９］ Ｑが酸素である［１］〜［８］いずれか一項記載のピリミジン化合物。
［１０］ Ｒ⁵がハロゲンもしくは−Ｌ³Ｒ¹⁴で置換されたＣ１−Ｃ１０アルキルまたはＣ３−Ｃ１０アルケニル基である［１］〜［９］いずれか一項記載のピリミジン化合物。
［１１］ Ｒ⁵がハロゲンで置換されたＣ１−Ｃ１０アルキルまたはＣ３−Ｃ１０アルケニル基である［１］〜［１０］いずれか１項記載のピリミジン化合物。
［１２］ Ｑが酸素であり、Ｇ¹が窒素またはＣＲ⁶であり、Ｒ¹およびＲ⁶が同一または相異なり、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鎖状炭化水素基であり、Ｒ²が水素、ハロゲン、ハロゲンで置換されていてもよいＣ１−Ｃ６鎖状炭化水素基、または−Ｌ¹Ｒ⁷であり、Ｒ³が水素、またはハロゲンで置換されていてもよいＣ１−Ｃ６鎖状炭化水素基であり、Ｒ⁴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鎖状炭化水素基であり、Ｒ⁵がハロゲンもしくは−Ｌ³Ｒ¹⁴で置換されたＣ１−Ｃ１０アルキルまたはＣ３−Ｃ１０アルケニル基である［１］記載のピリミジン化合物。
［１３］ ［１］〜［１２］いずれか一項記載のピリミジン化合物と不活性担体とを含有する有害生物防除剤。
［１４］ 有害生物を防除するための［１］〜［１２］いずれか一項記載のピリミジン化合物の使用。
［１５］ ［１］〜［１２］いずれか一項記載のピリミジン化合物の有効量を有害生物又は有害生物の生息場所に施用する工程を含む有害生物の防除方法。
［１６］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
［１７］５−メチル−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
［１８］５−クロロ−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
［１９］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
［２０］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
［２１］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
［２２］４−（２，２，３，３，４，４，５，５−オクタフルオロペンチロキシ）−５−メチル−６−（［１，２，４］トリアゾール−１−イル）−ピリミジン
［２３］５−クロロ−４−（２，２，３，３，４，４，５，５−オクタフルオロペンチロキシ）−６−（［１，２，４］トリアゾール−１−イル）−ピリミジン
［２４］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
［２５］４−（２，２−ジクロロプロポキシ）−５−メチル−６−（［１，２，４］トリアゾール−１−イル）−ピリミジン
［２６］
式（４）

〔式中、Ｑ’は酸素を表し、Ｒ³は水素を表し、Ｒ⁴は水素、ハロゲンまたはＣ１−Ｃ６鎖状炭化水素基を表し、Ｒ⁵は１個以上のハロゲンで置換されたＣ１−Ｃ１０アルキル基または１個以上のハロゲンで置換されたＣ３−Ｃ１０アルケニル基を表す。〕
で示されるピリミジン化合物。
［２７］
式（２）

〔式中、Ｇ^１は窒素またはＣＲ^６を表し、Ｒ⁶は水素を表し、Ｒ¹は水素またはハロゲンを表し、Ｒ²は水素、ハロゲンまたはアミノ基を表し、Ｒ³は水素を表し、Ｒ⁴はハロゲン、ニトロ基、シアノ基、または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。〕
で示されるピリミジン化合物。
［２８］
式（６）

〔式中、Ｇ^１は窒素またはＣＲ^６を表し、Ｒ⁶は水素を表し、Ｒ¹は水素またはハロゲンを表し、Ｒ²は水素、ハロゲンまたはアミノ基を表し、Ｒ³は水素を表し、Ｒ⁴はハロゲン、ニトロ基、シアノ基、または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。〕
で示されるピリミジン化合物。 As a result of studying to find a compound having a control activity against pests, the present inventor has found that a pyrimidine compound represented by the following formula (1) has a control effect on pests, leading to the present invention. It was.
That is, the present invention is as follows.

[1] Formula (1)

[Where,
Q represents oxygen or -S (O) n-
n represents 0, 1 or 2;
G ¹ represents nitrogen or CR ⁶
R ¹ , R ² and R ⁶ are the same or different and are hydrogen, halogen, nitro group, cyano group, C1-C6 chain hydrocarbon group optionally substituted with halogen, -L ¹ R ⁷ , -C ( = O) R ⁸ , to a phenyl group optionally substituted with one or more groups selected from group A or to a 5-membered or 6-membered aromatic optionally substituted with one or more groups selected from group A Represents a terrorist ring group,
L ¹ represents oxygen, —S (O) n— or —NR ⁹ —,
R ⁷ represents a C1-C6 chain hydrocarbon group which may be substituted with hydrogen or halogen (provided that when L ¹ is —S (O) n— and n is 1 or 2, ⁷ is not hydrogen)
R ⁸ is hydrogen, a hydroxy group, an amino group, a C1-C6 chain hydrocarbon group which may be substituted with halogen, a C1-C6 alkoxy group which may be substituted with halogen, or a halogen. A C1-C4 alkylamino group or a C2-C8 dialkylamino group optionally substituted with halogen,
R ⁹ represents hydrogen, a C1-C6 chain hydrocarbon group which may be substituted with halogen, or a C1-C6 alkylsulfonyl group which may be substituted with halogen,
R ³ represents hydrogen, halogen, a C1-C6 chain hydrocarbon group which may be substituted with halogen, a C3-C8 cycloalkyl group which may be substituted with halogen, or -L ² R ¹⁰ ;
R ⁴ is hydrogen, halogen, nitro group, cyano group, C1-C6 chain hydrocarbon group optionally substituted with halogen, C3-C8 cycloalkyl group optionally substituted with halogen, -L ² R ¹⁰ , -C (= O) R ¹¹ , a phenyl group optionally substituted with one or more groups selected from group A, or 5- or optionally substituted with one or more groups selected from group A Represents a 6-membered aromatic heterocyclic group,
L ² represents oxygen, —S (O) n— or —NR ¹² —,
When R ¹⁰ represents a hydrogen or halogen substituted C6 C1-may be a chain hydrocarbon group (provided, L ² is -S (O) is n-, n is 1 or 2, R ¹⁰ is not hydrogen)
R ¹¹ is hydrogen, a hydroxy group, an amino group, a C1-C6 chain hydrocarbon group optionally substituted with halogen, a C1-C6 alkoxy group optionally substituted with halogen, or optionally substituted with halogen. A C1-C4 alkylamino group or a C2-C8 dialkylamino group optionally substituted with halogen,
R ¹² represents hydrogen, a C1-C6 chain hydrocarbon group which may be substituted with halogen, or a C1-C6 alkylsulfonyl group which may be substituted with halogen;
R ⁵ represents a C1-C10 alkyl group substituted with one or more groups selected from Group B or a C3-C10 alkenyl group substituted with one or more groups selected from Group B;
Group A includes halogen, amino group, cyano group, nitro group, C1-C6 chain hydrocarbon group optionally substituted with halogen, C1-C6 alkoxy group optionally substituted with halogen, and S (O) nR. ¹³ wherein R ¹³ represents a C1-C6 alkyl group optionally substituted with halogen,
Group B is halogen, -L ³ R ^14, and -C (= O) R ^15,
{L ³ represents oxygen, —S (O) n—, —NR ¹⁶ — or —Si (R ¹⁷ ) ₂ —,
R ¹⁴ represents hydrogen or a C1-C6 chain hydrocarbon group which may be substituted with halogen (where L ³ is —S (O) n— and n is 1 or 2). , R ¹⁴ is not hydrogen)
R ¹⁵ is hydrogen, a C1-C6 chain hydrocarbon group which may be substituted with halogen, a C1-C4 alkylamino group which may be substituted with halogen, or a C2-C8 dialkylamino group which may be substituted with halogen. A C1-C6 alkoxy group optionally substituted with a group or halogen,
R ¹⁶ represents a hydrogen or halogen substituted C6 C1-may be a chain hydrocarbon group,
R ¹⁷ 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 pyrimidine compound represented by the following (hereinafter referred to as the present compound).
[2] R ¹ , R ² and R ⁶ are the same or different and are hydrogen, halogen, nitro group, cyano group, C1-C6 chain hydrocarbon group optionally substituted with halogen, -L ¹ R ⁷ or The pyrimidine compound according to [1], which is —C (═O) R ⁸ .
[3] R ¹ , R ² and R ⁶ are the same or different and are hydrogen, halogen, a C1-C6 chain hydrocarbon group optionally substituted with halogen, -L ¹ R ⁷ , or -C (= O ) The pyrimidine compound according to [1] or [2], which is R ⁸ .
[4] R ¹ and R ⁶ are the same or different and are hydrogen, halogen, a C1-C6 chain hydrocarbon group which may be substituted with halogen, or —C (═O) R ⁸ [1] to [3] The pyrimidine compound according to any one of the above.
[5] The pyrimidine compound according to any one of [1] to [4], wherein R ² is hydrogen, halogen, a C1-C6 chain hydrocarbon group which may be substituted with halogen, or -L ¹ R ⁷ . .
[6] R ⁴ is hydrogen, halogen, a C1-C6 chain hydrocarbon group which may be substituted with halogen, a C3-C8 cycloalkyl group which may be substituted with halogen, or -L ² R ¹⁰ . The pyrimidine compound according to any one of [1] to [5].
[7] R ³ is hydrogen, halogen, halogen-substituted C6 C1-may be a chain hydrocarbon group or a halogen optionally substituted C3-C8 cycloalkyl, [1] to [6 ] The pyrimidine compound as described in any one.
[8] The pyrimidine compound according to any one of [1] to [6], wherein R ³ is hydrogen.
[9] The pyrimidine compound according to any one of [1] to [8], wherein Q is oxygen.
[10] The pyrimidine compound according to any one of [1] to [9], wherein R ⁵ is a C1-C10 alkyl or C3-C10 alkenyl group substituted with halogen or —L ³ R ¹⁴ .
[11] The pyrimidine compound according to any one of [1] to [10], wherein R ⁵ is a C1-C10 alkyl or C3-C10 alkenyl group substituted with a halogen.
[12] C1-C6 chain hydrocarbon in which Q is oxygen, G ¹ is nitrogen or CR ⁶ , R ¹ and R ⁶ are the same or different and may be substituted with hydrogen, halogen, or halogen a group, R ² is hydrogen, halogen, halogen optionally substituted C1-C6 chain hydrocarbon group or -L ¹ R ^7,, optionally substituted R ³ are hydrogen or halogen, A good C1-C6 chain hydrocarbon group, R ⁴ is hydrogen, halogen, or a C1-C6 chain hydrocarbon group optionally substituted with halogen, and R ⁵ is halogen or -L ³ R ¹⁴ The pyrimidine compound according to [1], which is a substituted C1-C10 alkyl or C3-C10 alkenyl group.
[13] A pest control agent comprising the pyrimidine compound according to any one of [1] to [12] and an inert carrier.
[14] Use of the pyrimidine compound according to any one of [1] to [12] for controlling pests.
[15] A method for controlling pests comprising a step of applying an effective amount of the pyrimidine compound according to any one of [1] to [12] to a pest or a pest habitat.
[16] 4- (2,2,3,3-Tetrafluoropropoxy) -6-([1,2,4] triazol-1-yl) -pyrimidine [17] 5-methyl-4- (2,2 , 3,3-tetrafluoropropoxy) -6-([1,2,4] triazol-1-yl) -pyrimidine [18] 5-chloro-4- (2,2,3,3-tetrafluoropropoxy) -6-([1,2,4] triazol-1-yl) -pyrimidine [19] 4- (2,2,3,4,4,4-hexafluorobutyroxy) -6-([1,2, , 4] triazol-1-yl) -pyrimidine [20] 4- (2,2,3,4,4,4-hexafluorobutyroxy) -5-methyl-6-[[1,2,4] triazole -1-yl) -pyrimidine [21] 5-chloro-4- (2,2,3,4,4) 4-Hexafluorobutyoxy) -6-([1,2,4] triazol-1-yl) -pyrimidine [22] 4- (2,2,3,3,4,4,5,5-octafluoro Pentyloxy) -5-methyl-6-([1,2,4] triazol-1-yl) -pyrimidine [23] 5-chloro-4- (2,2,3,3,4,4,5,5) 5-octafluoropentyloxy) -6-([1,2,4] triazol-1-yl) -pyrimidine [24] 4- (2-chloro-2-methylpropoxy) -5-methyl-6-[[ 1,2,4] triazol-1-yl) -pyrimidine [25] 4- (2,2-dichloropropoxy) -5-methyl-6-[[1,2,4] triazol-1-yl) -pyrimidine [26]
Formula (4)

[Wherein, Q ′ represents oxygen, R ³ represents hydrogen, R ⁴ represents hydrogen, halogen or a C1-C6 chain hydrocarbon group, and R ⁵ represents C1-substituted with one or more halogens. A C10 alkyl group or a C3-C10 alkenyl group substituted with one or more halogens. ]
The pyrimidine compound shown by these.
[27]
Formula (2)

[Wherein, G ¹ represents nitrogen or CR ⁶ , R ⁶ represents hydrogen, R ¹ represents hydrogen or halogen, R ² represents hydrogen, halogen or an amino group, R ³ represents hydrogen, ⁴ represents a halogen, a nitro group, a cyano group, or a C1-C6 chain hydrocarbon group which may be substituted with a halogen. ]
The pyrimidine compound shown by these.
[28]
Formula (6)

[Wherein, G ¹ represents nitrogen or CR ⁶ , R ⁶ represents hydrogen, R ¹ represents hydrogen or halogen, R ² represents hydrogen, halogen or an amino group, R ³ represents hydrogen, ⁴ represents a halogen, a nitro group, a cyano group or a halogen-substituted C6 C1-may be a chain hydrocarbon group. ]
The pyrimidine compound shown by these.

In the compound of the present invention, “halogen” includes fluorine, chlorine, bromine and iodine.
In the compound of the present invention, examples of the “C1-C6 chain hydrocarbon group” include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, 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 compound of the present invention 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.
Examples of the “phenyl group optionally substituted with one or more groups selected from group A” in the compounds of the present invention include a phenyl group, a 2-chlorophenyl group, a 3-chlorophenyl group, a 4-chlorophenyl group, and a 2-amino group. Phenyl group, 3-aminophenyl group, 4-aminophenyl group, 2-cyanophenyl group, 3-cyanophenyl group, 4-cyanophenyl group, 2-nitrophenyl group, 3-nitrophenyl group, 4-nitrophenyl group 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 2- (trifluoromethyl) phenyl group, 3- (trifluoromethyl) phenyl group, 4- (trifluoromethyl) phenyl group, 2 -Methoxyphenyl group, 3-methoxyphenyl group, 4-methoxyphenyl group, 4- (trifluoromethoxy) phenyl group 4- (methylthio) phenyl group, 4- (methylsulfinyl) phenyl and 4- (methylsulfonyl) phenyl group.
In the compound of the present invention, examples of the “5- or 6-membered aromatic heterocyclic group” include 2-pyrrolyl group, 2-furyl group, 3-furyl group, 2-thienyl group, 3-thienyl group, and 5-pyrazolyl group. 4-pyrazolyl group, 2-pyridinyl group, 3-pyridinyl group, 4-pyridinyl group, pyrazinyl group, 1-pyrrolyl group and 1-pyrazolyl group.
In the compound of the present invention, examples of the “5- or 6-membered aromatic heterocyclic group optionally substituted with one or more groups selected from group A” include 1-methyl-2-pyrrolyl group, 2-furyl Group, 3-furyl group, 5-bromo-2-furyl group, 5-nitro-2-furyl group, 2-methyl-3-furyl group, 2,5-dimethyl-3-furyl group, 2,4-dimethyl -3-furyl group, 2-thienyl group, 3-thienyl group, 5-methyl-2-thienyl group, 3-methyl-2-thienyl group, 1-methyl-3-trifluoromethyl-5-pyrazolyl group, 5 -Chloro-1,3-dimethyl-4-pyrazolyl group, 2-pyridinyl group, 3-pyridinyl group, 4-pyridinyl group, 2-methyl-3-pyridinyl group, 6-methyl-3-pyridinyl group, 2-chloro -3-pyridinyl group, 6-chloro- - pyridinyl group, a pyrazinyl group, and a 1-pyrrolyl group and 1-pyrazolyl group.
Examples of the “C1-C6 alkoxy group optionally substituted with halogen” in the compound of the present invention 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-C6 alkylsulfonyl group optionally substituted with halogen” in the compound of the present invention include a methylsulfonyl group, a trifluoromethylsulfonyl group, and an ethylsulfonyl group.
Examples of the “C1-C4 alkylamino group optionally substituted with halogen” in the compounds of the present invention 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 compounds of the present invention include a dimethylamino group, a diethylamino group, a bis (2,2,2-trifluoroethyl) amino group, and a dipropylamino group. Groups.
Examples of the “C3-C8 cycloalkyl group optionally substituted with halogen” in the compounds of the present invention include a cyclopropyl group, a 2,2-difluorocyclopropyl group, a 2,2-dichlorocyclopropyl group, a 2,2- Examples include dibromocyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group and cyclooctyl group.
Examples of the “C1-C10 alkyl group substituted with one or more groups selected from group B” in the compounds of the present invention include, for example, 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-difluoropro Group, 2,3,3-trifluoropropyl group, 3,3,3-trifluoropropyl group, 2,2,3,3-tetrafluoropropyl group, 2,2,3,3,3-pentafluoro Propyl 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- Fluorobutyl group, 3,3-difluorobutyl group, 4,4-difluorobutyl group, 4,4,4-trifluorobutyl group, 2,2,3-trifluorobutyl group, 2,2,3,3- Tetrafluorobuty Group, 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, and 1,1 , 2,2,3,3,4,4-octafluorobutyl group, 2-methoxyethyl group, 2-trifluoromethoxyethyl group, 2-tert-butyloxyethyl group, 2- (tert-butylthio) ethyl group 2-dimethylaminoethyl group, 2- (dimethylamino) -2-methyl-propyl group, 1- (trimethylsilyl) methyl group, 2- (trimethylsilyl) ethyl group, 2- (methylamino) ethyl group, 2- ( Ethylamino) ethyl Group, 2- (2,2,2-trifluoroethylamino) ethyl group, 2- (propylamino) ethyl group, 2- (isopropylamino) ethyl group, 2- (butylamino) ethyl group, 2- (methoxy Examples include carbonyl) ethyl group and 2- (tert-butyloxycarbonyl) ethyl group.
Examples of the “C3-C10 alkenyl group substituted with one or more groups selected from group B” in the compounds of the present invention include, for example, 3,3-dichloro-2-propenyl group, 2,3,3-trichloro-2- Propenyl group, 3,3-difluoro-2-propenyl group, 2,3-difluoro-2-propenyl group, 4,4,4-trifluoro-2-butenyl group, 2,3,4,4,4-penta A fluoro-2-butenyl group, a 4-methoxy-2-propenyl group, a 4-methylthio-2-propenyl group, and a 4-dimethylamino-2-propenyl group can be mentioned.
Examples of the “C1-C6 alkyl group optionally substituted with halogen” in the compound of the present invention include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group. Pentyl group, isopentyl group, 1-methylbutyl group, tert-pentyl group, neopentyl group, hexyl group, isohexyl group, 1,1,1-trifluoromethyl group, 2,2,2-trifluoroethyl group and A 2,2,2-trichloroethyl group may be mentioned.

Examples of the compound of the present invention include the following pyrimidine compounds.
A pyrimidine compound represented by formula (1), wherein Q is oxygen;
A pyrimidine compound represented by formula (1), wherein Q is -S (O) n-;
The pyrimidine compound whose n is 0 in Formula (1).
The pyrimidine compound whose n is 1 in Formula (1).
The pyrimidine compound whose n is 2 in Formula (1).
In the formula (1), R ¹ is hydrogen, halogen, nitro group, cyano group, C1-C6 chain hydrocarbon group optionally substituted with halogen, —L ¹ R ⁷ , or —C (═O) R. A pyrimidine compound which is ⁸ .
A pyrimidine compound represented by formula (1), wherein R ¹ is hydrogen, halogen, a C1-C6 chain hydrocarbon group optionally substituted with halogen, -L ¹ R ⁷ , or -C (= O) R ⁸ .
A pyrimidine compound represented by formula (1), wherein R ¹ is hydrogen, halogen, or a C1-C6 chain hydrocarbon group optionally substituted with halogen.
A pyrimidine compound represented by formula (1), wherein R ¹ is hydrogen.
In the formula (1), R ² is hydrogen, halogen, nitro group, cyano group, C1-C6 chain hydrocarbon group optionally substituted with halogen, -L ¹ R ⁷ , or -C (= O) R. A pyrimidine compound which is ⁸ .
A pyrimidine compound represented by formula (1), wherein R ² is hydrogen, halogen, a C1-C6 chain hydrocarbon group which may be substituted with halogen, or -L ¹ R ⁷ .
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.
In Formula (1), R ¹ and R ² may be the same or different from each other, and may be hydrogen, halogen, a C1-C6 chain hydrocarbon group optionally substituted with halogen, or -L ¹ R ⁷ A pyrimidine compound.
A pyrimidine compound represented by formula (1), wherein R ¹ and R ² are hydrogen.

A pyrimidine compound represented by formula (1), wherein G ¹ is nitrogen.
A pyrimidine compound represented by formula (1), wherein G ¹ is CR ⁶ .
A pyrimidine compound represented by formula (1), wherein G ¹ is CR ⁶ and R ⁶ is hydrogen.
In Formula (1), R ¹ is hydrogen, halogen, a C1-C6 chain hydrocarbon group optionally substituted with halogen, -L ¹ R ⁷ , or -C (= O) R ⁸ , and R ² Is a hydrogen atom, halogen, a C1-C6 chain hydrocarbon group optionally substituted with halogen, or -L ¹ R ⁷ , G ¹ is nitrogen or CR ⁶ , and R ⁶ is hydrogen.
In the formula (1), R ¹ is hydrogen, halogen, or a C1-C6 chain hydrocarbon group which may be substituted with halogen, and R ² is C1- which may be substituted with hydrogen, halogen or halogen. A pyrimidine compound which is a C6 chain hydrocarbon group, or -L ¹ R ⁷ , G ¹ is nitrogen or CR ⁶ , and R ⁶ is hydrogen.
A pyrimidine compound represented by formula (1), wherein R ¹ is hydrogen, R ² is hydrogen or an amino group, G ¹ is nitrogen or CR ⁶ , and R ⁶ is hydrogen.

A pyrimidine compound represented by formula (1), wherein R ³ is hydrogen, halogen, a C1-C6 chain hydrocarbon group optionally substituted with halogen, or a C3-C8 cycloalkyl group optionally substituted with halogen.
A pyrimidine compound represented by formula (1), wherein R ³ is hydrogen, a C1-C6 chain hydrocarbon group optionally substituted with halogen, or -L ² R ¹⁰ .
A pyrimidine compound represented by formula (1), wherein R ³ is a C1-C6 chain hydrocarbon group optionally substituted with hydrogen or halogen.
A pyrimidine compound represented by formula (1), wherein R ³ is hydrogen.
In the formula (1), R ⁴ is hydrogen, halogen, nitro group, cyano group, C1-C6 chain hydrocarbon group optionally substituted with halogen, C3-C8 cycloalkyl group optionally substituted with halogen. , -L ² R ¹⁰ or -C (= O) pyrimidine compound is R ^11,.
In formula (1), R ⁴ is substituted with hydrogen, halogen, a C1-C6 chain hydrocarbon group optionally substituted with halogen, -L ² R ¹⁰ , or one or more groups selected from group A. A pyrimidine compound which is an optionally substituted phenyl group.
In the formula (1), R ⁴ is hydrogen, halogen, nitro group, cyano group, C1-C6 chain hydrocarbon group optionally substituted with halogen, C3-C8 cycloalkyl group optionally substituted with halogen. Or a pyrimidine compound of -C (= O) R ¹¹ .
In Formula (1), R ⁴ is hydrogen, halogen, a C1-C6 chain hydrocarbon group which may be substituted with halogen, a C3-C8 cycloalkyl group which may be substituted with halogen, or -L ² R A pyrimidine compound which is ¹⁰ .
A pyrimidine compound represented by formula (1), wherein R ⁴ is hydrogen, chlorine or a methyl group.
In the formula (1), R ³ is hydrogen, and R ⁴ is hydrogen, halogen, nitro group, cyano group, C1-C6 chain hydrocarbon group which may be substituted with halogen, or halogen. good C3-C8 cycloalkyl group, -L ² R ¹⁰ or -C (= O) pyrimidine compound is R ^11,.
A pyrimidine compound represented by formula (1), wherein R ³ is hydrogen and R ⁴ is hydrogen, halogen, a C1-C6 chain hydrocarbon group which may be substituted with halogen, or -L ² R ¹⁰ .
A pyrimidine compound represented by formula (1), wherein R ³ is hydrogen and R ⁴ is hydrogen, chlorine, or a methyl group.

In the formula (1), R ¹ , R ² and R ⁶ are the same or different and are hydrogen, halogen, nitro group, cyano group, C1-C6 chain hydrocarbon group which may be substituted with halogen, -L ¹ The pyrimidine compound which is R < ⁷ > or -C (= O) R < ⁸ >.
In the formula (1), R ¹ , R ² and R ⁶ are the same or different and are each hydrogen, halogen, a C1-C6 chain hydrocarbon group optionally substituted with halogen, -L ¹ R ⁷ or -C ( = O) pyrimidine compound is R ^8.
A pyrimidine compound represented by formula (1), wherein R ¹ and R ⁶ are the same or different and are hydrogen, halogen, a C1-C6 chain hydrocarbon group optionally substituted with halogen, or —C (═O) R ⁸ .
In Formula (1), R ¹ is hydrogen, halogen, a C1-C6 chain hydrocarbon group which may be substituted with halogen, -L ¹ R ⁷ , or -C (= O) R ⁸ , and R ² Is hydrogen, halogen, a C1-C6 chain hydrocarbon group optionally substituted with halogen, or -L ¹ R ⁷ , G ¹ is nitrogen or CR ⁶ , R ⁶ is hydrogen, R ³ Is hydrogen, R ⁴ is hydrogen, halogen, a C1-C6 chain hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen, or -L ² R ¹⁰ A pyrimidine compound.
In the formula (1), R ¹ is hydrogen, halogen, or a C1-C6 chain hydrocarbon group which may be substituted with halogen, and R ² is C1- which may be substituted with hydrogen, halogen or halogen. C6 chain hydrocarbon group, or -L ¹ R ⁷ , G ¹ is nitrogen or CR ⁶ , R ⁶ is hydrogen, R ³ is hydrogen, R ⁴ is substituted with hydrogen, halogen, halogen pyrimidine compound is a -L ² R ¹⁰ hydrocarbon group or may also be a chain C1-C6 have been.

A pyrimidine compound represented by formula (1), wherein R ⁵ is a halogen or a C1-C10 alkyl group substituted with -L ³ R ¹⁴ , and L ³ is oxygen, sulfur, or -Si (R ¹⁷ ) _2- .
A pyrimidine compound represented by formula (1), wherein R ⁵ is a C1-C10 alkyl group substituted with -L ³ R ¹⁴ .
In the formula (1), a C1-C10 alkyl group R ⁵ is substituted with -L ³ R ^14, L ³ is oxygen, sulfur or -Si (R ¹⁷⁾ _2, - a is pyrimidine compound.
A pyrimidine compound represented by formula (1), wherein R ⁵ is a C1-C10 alkyl group substituted with halogen.
A pyrimidine compound represented by formula (1), wherein R ⁵ is a C1-C10 alkyl group substituted with 1 to 8 halogens.
A pyrimidine compound represented by formula (1), wherein R ⁵ is a C2-C6 alkyl group substituted with 1 to 8 halogens.
A pyrimidine compound represented by formula (1), wherein R ⁵ is a C3-C6 alkyl group substituted with 1 to 8 halogens.
A pyrimidine compound represented by formula (1), wherein R ⁵ is a C1-C10 alkyl group substituted with 1 to 8 fluorines.
A pyrimidine compound represented by formula (1), wherein R ⁵ is a C2-C6 alkyl group substituted with 1 to 8 fluorines.
A pyrimidine compound represented by formula (1), wherein R ⁵ is a C3-C6 alkyl group substituted with 1 to 8 fluorines.
A pyrimidine compound represented by formula (1), wherein R ⁵ is a C1-C10 alkyl group substituted with 1 to 8 chlorines.
In the formula (1), R ⁵ 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, perfluoroisopropyl 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-octafluoropentyl group Pyrimidine compound.

A pyrimidine compound represented by formula (1), wherein R ⁵ is a halogen or C 3 -C 10 alkenyl group substituted with —L ³ R ¹⁴ , and L ³ is oxygen, sulfur, or —Si (R ¹⁷ ) ₂ —.
A pyrimidine compound represented by formula (1), wherein R ⁵ is a C3-C10 alkenyl group substituted with -L ³ R ¹⁴ , and L ³ is oxygen, sulfur, or -Si (R ¹⁷ ) _2- .
A pyrimidine compound represented by formula (1), wherein R ⁵ is a C3-C10 alkenyl group substituted with halogen.
A pyrimidine compound represented by formula (1), wherein R ⁵ is a C3-C10 alkenyl group substituted with 1 to 8 halogens.
In the formula (1), pyrimidine compound is C3-C6 alkenyl group R ⁵ is substituted by one to eight halogens.
A pyrimidine compound represented by formula (1), wherein R ⁵ is a C3-C10 alkenyl group substituted with 1 to 8 fluorines.
A pyrimidine compound represented by formula (1), wherein R ⁵ is a C3-C6 alkenyl group substituted with 1 to 8 fluorines.
A pyrimidine compound represented by formula (1), wherein R ⁵ is a C3-C10 alkenyl group substituted with 1 to 8 chlorines.
In the formula (1), R ⁵ is 3,3-dichloro-2-propenyl group, 2,3,3-trichloro-2-propenyl group, 3,3-difluoro-2-propenyl group, 4,4,4 A pyrimidine compound which is a trifluoro-2-butenyl group or a 2,3,4,4,4-pentafluoro-2-butenyl group.

A pyrimidine compound represented by formula (1), wherein R ⁵ is a C1-C10 alkyl or C3-C10 alkenyl group substituted with halogen or -L ³ R ¹⁴ .
In Formula (1), R ⁵ is a C1-C10 alkyl or C3-C10 alkenyl group substituted with halogen or —L ³ R ¹⁴ , and L ³ is oxygen, sulfur or —Si (R ¹⁷ ) ₂ —. Pyrimidine compounds.
In formula (1), R ⁵ is a C1-C10 alkyl or C3-C10 alkenyl group substituted with -L ³ R ¹⁴ , and L ³ is oxygen, sulfur, or —Si (R ¹⁷ ) ₂ —. Compound.
A pyrimidine compound represented by formula (1), wherein R ⁵ is a C1-C10 alkyl or C3-C10 alkenyl group substituted with halogen.
In formula (1), Q is oxygen, R ⁵ is a C1-C10 alkyl or C3-C10 alkenyl group substituted with halogen or —L ³ R ¹⁴ , and L ³ is oxygen, sulfur, or —Si ( A pyrimidine compound which is R ¹⁷ ) _2- .
In the formula (1), Q is oxygen, R ⁵ is a C1-C10 alkyl or C3-C10 alkenyl group substituted with —L ³ R ¹⁴ , and L ³ is oxygen, sulfur or —Si (R ¹⁷ ). A pyrimidine compound which is _2- .
A pyrimidine compound represented by formula (1), wherein Q is oxygen and R ⁵ is a C1-C10 alkyl or C3-C10 alkenyl group substituted with halogen.
In the formula (1), Q is oxygen, R ⁵ 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, 2,2,3, 3,4,4,5,5-octafluoropen Group, 3,3-dichloro-2-propenyl group, 2,3,3-trichloro-2-propenyl group, 3,3-difluoro-2-propenyl group, 4,4,4-trifluoro-2-butenyl Group, or a pyrimidine compound which is a 2,3,4,4,4-pentafluoro-2-butenyl group.

In equation (1),
Q is oxygen, G ¹ is nitrogen, or CR ⁶ , and R ¹ and R ⁶ are the same or different and each is hydrogen, halogen, or a C1-C6 chain hydrocarbon group optionally substituted with halogen R ² is hydrogen, halogen, a C1-C6 chain hydrocarbon group which may be substituted with halogen, or -L ¹ R ⁷ , and R ³ is hydrogen or halogen-substituted C1-C6 C1 having a chain hydrocarbon group, R ⁴ being hydrogen, halogen, or a C1-C6 chain hydrocarbon group optionally substituted with halogen, and R ⁵ being substituted with halogen or -L ³ R ¹⁴ A pyrimidine compound which is a C10 alkyl or C3-C10 alkenyl group.

In formula (1), Q is oxygen, G ¹ is nitrogen or CR ⁶ , R ¹ is hydrogen, halogen, a C1-C6 chain hydrocarbon group optionally substituted with halogen, -L ¹ R ⁷ or -C (= O) a R ^8, R ² is hydrogen, halogen or halogen-substituted C6 C1-may be a chain hydrocarbon group, or -L ¹ R ^7,, R ^6, Is hydrogen, R ³ is a C1-C6 chain hydrocarbon group optionally substituted with hydrogen or halogen, or -L ² R ¹⁰ , and R ⁴ is substituted with hydrogen, halogen or halogen A good C1-C6 chain hydrocarbon group, a C3-C8 cycloalkyl group optionally substituted with halogen, or -L ² R ¹⁰ , wherein R ⁵ is substituted with one or more groups selected from group B Substituted with a C1-C10 alkyl group or one or more groups selected from group B Pyrimidine compound is C3-C10 alkenyl group.

In the formula (1), Q is oxygen, G ¹ is nitrogen or CR ⁶ , R ¹ is hydrogen, halogen, or a C1-C6 chain hydrocarbon group which may be substituted with halogen, R ² is a C1-C6 chain hydrocarbon group optionally substituted with hydrogen, halogen, or halogen, or —L ¹ R ⁷ , R ⁶ is hydrogen, and R ³ is substituted with hydrogen or halogen. An optionally substituted C1-C6 chain hydrocarbon group, R ⁴ is hydrogen, halogen, a C1-C6 chain hydrocarbon group optionally substituted with halogen, or -L ² R ¹⁰ , and R ⁵ is halogen or -L a C1-C10 alkyl or C3-C10 alkenyl group substituted with ³ R ^14, L ³ is oxygen, sulfur or -Si (R ¹⁷⁾ ₂ - a is pyrimidine compound.

In the formula (1), Q is oxygen, G ¹ is nitrogen or CR ⁶ , R ¹ is hydrogen, halogen, or methyl group, and R ² is hydrogen, halogen, methyl group, or amino group , R ⁶ is hydrogen, R ³ is a C1-C6 chain hydrocarbon group optionally substituted with hydrogen or halogen, or -L ² R ¹⁰ , and R ⁴ is substituted with hydrogen, halogen or halogen. An optionally substituted C1-C6 chain hydrocarbon group, an optionally substituted C3-C8 cycloalkyl group, or —L ² R ¹⁰ , wherein R ⁵ is substituted with halogen or —L ³ R ¹⁴ A pyrimidine compound which is a C1-C10 alkyl or C3-C10 alkenyl group and L ³ is oxygen, sulfur, or —Si (R ¹⁷ ) ₂ —.

In equation (1),
Q is oxygen, G ¹ is nitrogen or CR ⁶ , R ¹ is hydrogen or halogen, R ² is hydrogen, halogen, methyl group or amino group, R ⁶ is hydrogen, R ³ Is a C1-C6 chain hydrocarbon group optionally substituted with hydrogen or halogen, R ⁴ is a C1-C6 chain hydrocarbon group optionally substituted with hydrogen, halogen, halogen, or -L ² R ¹⁰ , R ⁵ is a C1-C10 alkyl or C3-C10 alkenyl group substituted with halogen or —L ³ R ¹⁴ , and L ³ is oxygen, sulfur, or —Si (R ¹⁷ ) ₂ —. Pyrimidine compounds.

In the formula (1), Q is oxygen, G ¹ is nitrogen or CR ⁶ , R ¹ is hydrogen, R ² is hydrogen or an amino group, R ⁶ is hydrogen, and R ³ is hydrogen R ⁴ is hydrogen, halogen, a C1-C6 chain hydrocarbon group optionally substituted with halogen, and R ⁵ is C1-C10 alkyl substituted with halogen or -L ³ R ¹⁴ or C3- A pyrimidine compound which is a C10 alkenyl group and L ³ is oxygen, sulfur, or —Si (R ¹⁷ ) ₂ —.

In the formula (1), Q is oxygen, G ¹ is nitrogen or CR ⁶ , R ¹ is hydrogen or halogen, R ² is hydrogen, halogen, methyl group, or amino group, and R ⁶ is A C1-C6 chain hydrocarbon group that is hydrogen, R ³ may be substituted with hydrogen or halogen, and R ⁴ is a C1-C6 chain hydrocarbon group that may be substituted with hydrogen, halogen, or halogen Or a pyrimidine compound wherein -L ² R ¹⁰ and R ⁵ is a C1-C10 alkyl or C3-C10 alkenyl group substituted with halogen.

In the formula (1), Q is oxygen, G ¹ is nitrogen, R ¹ is hydrogen or halogen, R ² is hydrogen, halogen or amino group, R ³ is hydrogen, R ⁴ is Pyrimidine which is hydrogen, halogen, C1-C6 chain hydrocarbon group, and R ⁵ is a C1-C10 alkyl group substituted with one or more halogens or a C3-C10 alkenyl group substituted with one or more halogens Compound.

Next, the manufacturing method of this invention compound is demonstrated.
The compound of the present invention can be produced, for example, according to the following (Production Method A) to (Production Method E).

〔式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵およびＧ¹は、前記と同じ意味を表し、Ｑ’は酸素または硫黄を表す。〕
で示される化合物（以下、本発明化合物（１−ｉ）と記す。）は、
式（２）

〔式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴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、Ｒ⁵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。 (Production method A)
Among the compounds of the present invention,
Formula (1-i)

[Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ and G ¹ represent the same meaning as described above, and Q ′ represents oxygen or sulfur. ]
(Hereinafter referred to as the present compound (1-i))
Formula (2)

[Wherein R ¹ , R ² , R ³ , R ⁴ and G ¹ represent the same meaning as described above. ]
A compound represented by (hereinafter referred to as compound (2)),
Formula (3)

[Wherein, R ⁵ and Q ′ represent the same meaning as described above. ]
It can manufacture by making the compound (henceforth a compound (3)) 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, 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 the compound (3) used in the reaction is usually 1 to 2 moles relative to 1 mole of the 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 compound (1-i) of the present invention 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 (1-i) of the present invention can be further purified by recrystallization, chromatography or the like.

Examples of the compound (2) include the following pyrimidine compounds.
A pyrimidine compound represented by formula (2), wherein G ¹ is nitrogen.
A pyrimidine compound represented by formula (2), wherein G ¹ is CR ⁶ and R ⁶ is hydrogen.
A pyrimidine compound represented by formula (2), wherein R ¹ is hydrogen.
A pyrimidine compound represented by formula (2), wherein R ² is hydrogen.
A pyrimidine compound represented by formula (2), wherein R ¹ and R ² are hydrogen.
A pyrimidine compound represented by formula (2), wherein G ¹ is nitrogen, and R ¹ and R ² are hydrogen.
In the formula (2), pyrimidine compounds wherein ^{R 3} is hydrogen.
A pyrimidine compound represented by formula (2), wherein G ¹ is nitrogen and R ³ is hydrogen.
A pyrimidine compound represented by formula (2), wherein G ¹ is CR ⁶ , R ⁶ is hydrogen, and R ³ is hydrogen.
In the formula (2), R ⁴ is hydrogen, halogen, nitro group, cyano group, C1-C6 chain hydrocarbon group optionally substituted with halogen, C3-C8 cycloalkyl group optionally substituted with halogen. Or a pyrimidine compound of -C (= O) R ¹¹ .
In Formula (2), R ⁴ is hydrogen, halogen, a C1-C6 chain hydrocarbon group that may be substituted with halogen, a C3-C8 cycloalkyl group that may be substituted with halogen, or -L ² R A pyrimidine compound which is ¹⁰ . .
In the formula (2), R ⁴ is halogen, nitro group, cyano group, C1-C6 chain hydrocarbon group which may be substituted with halogen, C3-C8 cycloalkyl group which may be substituted with halogen, or A pyrimidine compound which is -C (= O) R ¹¹ .
In the formula (2), R ³ is hydrogen, and R ⁴ is hydrogen, halogen, nitro group, cyano group, C1-C6 chain hydrocarbon group which may be substituted with halogen, or halogen. good C3-C8 cycloalkyl group, -L ² R ¹⁰ or -C (= O) pyrimidine compound is R ^11.
A pyrimidine compound represented by formula (2), wherein R ³ is hydrogen and R ⁴ is hydrogen, halogen, a C1-C6 chain hydrocarbon group optionally substituted with halogen, or -L ² R ¹⁰ .
In formula (2), R ³ is hydrogen, R ⁴ is halogen, halogen optionally substituted C1-C6 chain hydrocarbon group or pyrimidine compound is a -L ² R ^10,.
A pyrimidine compound represented by formula (2), wherein R ³ is hydrogen and R ⁴ is hydrogen, chlorine or a methyl group.
In the formula (2), G ¹ is nitrogen or CR ⁶ , R ⁶ is hydrogen, R ¹ is hydrogen or halogen, R ² is hydrogen, halogen or amino group, and R ³ is hydrogen , R ⁴ is a pyrimidine compound in which R ⁴ is a halogen, a nitro group, a cyano group, or a C1-C6 chain hydrocarbon group optionally substituted with a halogen.
In the formula (2), G ¹ is nitrogen, R ¹ is hydrogen or halogen, R ² is hydrogen, halogen or amino group, R ³ is hydrogen, R ⁴ is hydrogen, halogen, or C 1 A pyrimidine compound which is a C6 chain hydrocarbon group.
A pyrimidine compound represented by formula (2), wherein G ¹ is nitrogen, R ¹ and R ² are hydrogen, R ³ is hydrogen, and R ⁴ is hydrogen, chlorine, or a methyl group.

〔式中、Ｒ³、Ｒ⁴、Ｒ⁵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（４）と記す。）と、
式（５）

〔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（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。 (Production method B)
The compound (1-i) of the present invention is
Formula (4)

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

[Wherein, R ¹ , R ² and G ¹ represent 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 compound (1-i) of the present invention 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 (1-i) of the present invention can be further purified by recrystallization, chromatography or the like.

Examples of the compound (4) include the following pyrimidine compounds.
A pyrimidine compound represented by formula (4), wherein R ³ is hydrogen.
In the formula (4), R ⁴ is hydrogen, halogen, nitro group, cyano group, C1-C6 chain hydrocarbon group which may be substituted with halogen, C3-C8 cycloalkyl group which may be substituted with halogen. or -C (= O) pyrimidine compound is R ^11.
In the formula (4), R ⁴ is hydrogen, halogen, halogen-substituted C6 C1-may be a chain hydrocarbon group, a halogen or C3-C8 optionally substituted cycloalkyl group or -L ² R ¹⁰ A pyrimidine compound. .
A pyrimidine compound represented by formula (4), wherein R ⁴ is hydrogen, halogen, or a C1-C6 chain hydrocarbon group optionally substituted with halogen.
In Formula (4), R ³ is hydrogen, and R ⁴ is hydrogen, halogen, nitro group, cyano group, C1-C6 chain hydrocarbon group which may be substituted with halogen, or halogen. good C3-C8 cycloalkyl group, -L ² R ¹⁰ or -C (= O) pyrimidine compound is R ^11.
A pyrimidine compound represented by formula (4), wherein R ³ is hydrogen and R ⁴ is hydrogen, halogen, a C1-C6 chain hydrocarbon group which may be substituted with halogen, or -L ² R ¹⁰ .
A pyrimidine compound represented by formula (4), wherein R ³ is hydrogen and R ⁴ is hydrogen, chlorine or a methyl group.
A pyrimidine compound represented by formula (4), wherein R ⁵ is a C1-C10 alkyl or C3-C10 alkenyl group substituted with halogen or -L ³ R ¹⁴ .
In Formula (4), R ⁵ is a C1-C10 alkyl or C3-C10 alkenyl group substituted with halogen or —L ³ R ¹⁴ , and L ³ is oxygen, sulfur or —Si (R ¹⁷ ) ₂ —. Pyrimidine compounds.
In the formula (4), a C1-C10 alkyl or C3-C10 alkenyl group R ⁵ is substituted with -L ³ R ^14, L ³ is oxygen, sulfur or -Si (R ¹⁷⁾ ₂ - a is pyrimidine compound .
A pyrimidine compound represented by formula (4), wherein R ⁵ is a C1-C10 alkyl or C3-C10 alkenyl group substituted with halogen.
A pyrimidine compound represented by formula (4), wherein R ⁵ is a C1-C10 alkyl group substituted with one or more fluorine atoms or a C3-C10 alkenyl group substituted with one or more fluorine atoms.
In the formula (4), Q 'is oxygen, C1-C10 alkyl or C3-C10 alkenyl group R ⁵ is substituted by halogen or -L ³ R ^14, L ³ is oxygen, sulfur or -Si ( A pyrimidine compound which is R ¹⁷ ) _2- .
In Formula (4), Q ′ is oxygen, R ⁵ is a C1-C10 alkyl or C3-C10 alkenyl group substituted with —L ³ R ¹⁴ , and L ³ is oxygen, sulfur or —Si (R ¹⁷ ₂ ) A pyrimidine compound which is _2- .
In the formula (4), Q 'is oxygen, pyrimidine compounds wherein R ⁵ is C1-C10 alkyl or C3-C10 alkenyl group substituted with halogen.

In Formula (4), Q ′ is oxygen, R ³ is hydrogen, R ⁴ is hydrogen, halogen, or a C1-C6 chain hydrocarbon group, and R ⁵ is substituted with one or more halogens. A pyrimidine compound which is a C1-C10 alkyl group or a C3-C10 alkenyl group substituted with one or more halogens.
In formula (4), Q ′ is oxygen, R ³ is hydrogen, R ⁴ is hydrogen, chlorine or a methyl group, and R ⁵ is a C1-C10 alkyl group substituted with one or more fluorines or A pyrimidine compound which is a C3-C10 alkenyl group substituted with one or more fluorines.
In the formula (4), Q ′ is oxygen, R ³ is hydrogen, R ⁴ is hydrogen, chlorine or methyl group, R ⁵ is 2,2-dichloropropyl group, 2-chloro-2-methyl Propyl 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, perfluoroisopropyl group, 4,4,4-trifluorobutyl group, 2,2,3,3,4,4,4-heptafluoro Butyl 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 a 2,2,3,3,4,4,5,5-octafluoropentyl group.

〔式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴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。 (Production method C)
The compound (1-i) of the present invention is
Formula (6)

[Wherein R ¹ , R ² , R ³ , R ⁴ 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 compound (1-i) of the present invention 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 (1-i) of the present invention can be further purified by recrystallization, chromatography or the like.

Examples of the compound (6) include the following pyrimidine compounds.
A pyrimidine compound represented by formula (6), wherein G ¹ is nitrogen.
A pyrimidine compound represented by formula (6), wherein G ¹ is CR ⁶ and R ⁶ is hydrogen.
A pyrimidine compound represented by formula (6), wherein R ¹ is hydrogen.
A pyrimidine compound represented by formula (6), wherein R ² is hydrogen.
A pyrimidine compound represented by formula (6), wherein R ¹ and R ² are hydrogen.
A pyrimidine compound represented by formula (6), wherein G ¹ is nitrogen, and R ¹ and R ² are hydrogen.
A pyrimidine compound represented by formula (6), wherein R ³ is hydrogen.
A pyrimidine compound represented by formula (6), wherein G ¹ is nitrogen and R ³ is hydrogen.
A pyrimidine compound represented by formula (6), wherein G ¹ is CR ⁶ , R ⁶ is hydrogen, and R ³ is hydrogen.
In the formula (6), R ⁴ is hydrogen, halogen, nitro group, cyano group, C1-C6 chain hydrocarbon group optionally substituted with halogen, C3-C8 cycloalkyl group optionally substituted with halogen. or -C (= O) pyrimidine compound is R ^11.
In the formula (6), R ⁴ is hydrogen, halogen, a C1-C6 chain hydrocarbon group which may be substituted with halogen, a C3-C8 cycloalkyl group which may be substituted with halogen, or -L ² R ^10. A pyrimidine compound.
In the formula (6), R ⁴ is halogen, nitro group, cyano group, C1-C6 chain hydrocarbon group which may be substituted with halogen, C3-C8 cycloalkyl group which may be substituted with halogen, or — C (= O) pyrimidine compound is R ^11.
In Formula (6), R ³ is hydrogen and R ⁴ is hydrogen, halogen, nitro group, cyano group, C1-C6 chain hydrocarbon group which may be substituted with halogen, or halogen good C3-C8 cycloalkyl group, -L ² R ¹⁰ or -C (= O) pyrimidine compound is R ^11.
In the formula (6), R ³ is hydrogen, R ⁴ is hydrogen, halogen, halogen is optionally may C1-C6 chain also substituted hydrocarbon group or -L ² R pyrimidine compound ^10.
A pyrimidine compound represented by formula (6), wherein R ³ is hydrogen and R ⁴ is halogen, a C1-C6 chain hydrocarbon group which may be substituted with halogen, or -L ² R ¹⁰ .
A pyrimidine compound represented by formula (6), wherein R ³ is hydrogen and R ⁴ is hydrogen, chlorine or a methyl group.
In the formula (6), G ¹ is nitrogen or CR ⁶ , R ⁶ is hydrogen, R ¹ is hydrogen or halogen, R ² is hydrogen, halogen or amino group, and R ³ is hydrogen , R ⁴ is a pyrimidine compound in which R ⁴ is a halogen, a nitro group, a cyano group, or a C1-C6 chain hydrocarbon group which may be substituted with a halogen.
In Formula (6), G ¹ is nitrogen, R ¹ is hydrogen or halogen, R ² is hydrogen, halogen or amino group, R ³ is hydrogen, R ⁴ is hydrogen, halogen, or C 1 A pyrimidine compound which is a C6 chain hydrocarbon group.
A pyrimidine compound represented by formula (6), wherein G ¹ is nitrogen, R ¹ and R ² are hydrogen, R ³ is hydrogen, and R ⁴ is hydrogen, chlorine or a methyl group.

〔式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、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、Ｒ⁵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。 (Production method D)
The compound (1-i) of the present invention is
Formula (7)

[Wherein, R ¹ , R ² , R ³ , R ⁴ , G ¹ and Q ′ represent the same meaning as described above. ]
A compound represented by formula (hereinafter referred to as compound (7)),
Formula (8)

[Wherein, R ⁵ 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 shown below (it is hereafter described as a compound (8)) 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 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.
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 (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 compound (1-i) of the present invention 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 (1-i) of the present invention can be further purified by recrystallization, chromatography or the like.

Examples of the compound (7) include the following pyrimidine compounds.
A pyrimidine compound represented by formula (7), wherein G ¹ is nitrogen.
A pyrimidine compound represented by formula (7), wherein G ¹ is CR ⁶ and R ⁶ is hydrogen.
In the formula (7), pyrimidine compound ^{wherein R 1} is hydrogen.
A pyrimidine compound represented by formula (7), wherein R ² is hydrogen.
A pyrimidine compound represented by formula (7), wherein R ¹ and R ² are hydrogen.
A pyrimidine compound represented by formula (7), wherein G ¹ is nitrogen, and R ¹ and R ² are hydrogen.
A pyrimidine compound represented by formula (7), wherein R ³ is hydrogen.
A pyrimidine compound represented by formula (7), wherein G ¹ is nitrogen and R ³ is hydrogen.
A pyrimidine compound represented by formula (7), wherein G ¹ is CR ⁶ , R ⁶ is hydrogen, and R ³ is hydrogen.
In the formula (7), R ⁴ is hydrogen, halogen, nitro group, cyano group, C1-C6 chain hydrocarbon group which may be substituted with halogen, C3-C8 cycloalkyl group which may be substituted with halogen. or -C (= O) pyrimidine compound is R ^11.
In the formula (7), R ⁴ is hydrogen, halogen, a C1-C6 chain hydrocarbon group which may be substituted with halogen, a C3-C8 cycloalkyl group which may be substituted with halogen, or —L ² R ^10. A pyrimidine compound.
In the formula (7), R ⁴ is halogen, nitro group, cyano group, halogen-substituted C6 C1-may be a chain hydrocarbon group may C3-C8 cycloalkyl group or optionally substituted with halogen - A pyrimidine compound represented by C (═O) R ¹¹ .
In the formula (7), R ³ is hydrogen, and R ⁴ is hydrogen, halogen, nitro group, cyano group, C1-C6 chain hydrocarbon group which may be substituted with halogen, or halogen. good C3-C8 cycloalkyl group, -L ² R ¹⁰ or -C (= O) pyrimidine compound is R ^11.
A pyrimidine compound represented by formula (7), wherein R ³ is hydrogen and R ⁴ is hydrogen, halogen, a C1-C6 chain hydrocarbon group which may be substituted with halogen, or -L ² R ¹⁰ .
A pyrimidine compound represented by formula (7), wherein R ³ is hydrogen and R ⁴ is halogen, a C1-C6 chain hydrocarbon group which may be substituted with halogen, or -L ² R ¹⁰ .
A pyrimidine compound represented by formula (7), wherein R ³ is hydrogen and R ⁴ is hydrogen, chlorine or a methyl group.
A pyrimidine compound represented by formula (7), wherein Q 'is oxygen, R ³ is hydrogen, and R ⁴ is hydrogen, chlorine, or a methyl group.
In formula (7), pyrimidine in which G ¹ is nitrogen, R ¹ and R ² are hydrogen, Q ′ is oxygen, R ³ is hydrogen, and R ⁴ is hydrogen, chlorine, or a methyl group Compound.

〔式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵およびＧ¹は前記と同じ意味を表し、Ｑ”は−Ｓ（Ｏ）−または−Ｓ（Ｏ）₂−を表す。〕
で示される化合物（以下、本発明化合物（１−ｉｉ）と記す。）は、
式（１−ｉｉｉ）

〔式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵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（１−ｉｉｉ）と記す。）と酸化剤とを反応させることにより製造することができる。 (Production method E)
Among the compounds of the present invention,
Formula (1-ii)

[Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ and G ¹ represent the same meaning as described above, and Q ″ represents —S (O) — or —S (O) ₂ —.]
(Hereinafter, referred to as the present compound (1-ii))
Formula (1-iii)

[Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁵ and G ¹ represent the same meaning as described above. ]
It can manufacture by making the compound (henceforth a compound (1-iii)) shown by these and an oxidizing agent react.

  Next, the manufacturing method of the manufacturing intermediate of this invention 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、Ｒ³およびＲ⁴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。 (Reference production method 1)
Compound (2) is
Formula (9)

[Wherein R ³ and R ⁴ represent the same meaning as described above. ]
A compound represented by formula (hereinafter referred to as compound (9)),
It can be produced by reacting 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 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 -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) 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) can be further purified by recrystallization, chromatography or the like.

〔式中、Ｒ¹、Ｒ³およびＲ⁴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（１０）

〔式中、Ｒ³およびＲ⁴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、Ｒ¹⁴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。 (Reference production method 2)
Of the compounds (2)
Formula (2-i)

Wherein, R ^1, R ³ and R ⁴ are as defined above. ]
(Hereinafter referred to as compound (2-i))
Formula (10)

[Wherein R ³ and R ⁴ represent the same meaning as described above. ]
A compound represented by formula (hereinafter referred to as compound (10)),
Formula (11)

[Wherein, R ¹⁴ 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; 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-i) can be isolated by pouring the reaction mixture into water, extracting with an organic solvent, and concentrating the organic layer. The isolated compound (2-i) 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; 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) is
It 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 compound (3) used in the reaction is usually 1 to 2 moles relative to 1 mole of 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.

(Reference production method 5)
Compound (6) is
It 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 compound (5) used in the reaction is usually 2 to 3 moles per 1 mole of 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) 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) can be further purified by recrystallization, chromatography or the like.

〔式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴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、例えば式（Ｙ）

で示される化合物を加水分解反応に付すことで製造することができる。 (Reference production method 6)
Of compounds (7)
Formula (7-i)

[Wherein R ¹ , R ² , R ³ , R ⁴ and G ¹ represent the same meaning as described above. ]
The compound represented by the formula (hereinafter referred to as compound (7-i)) is, for example, the formula (Y).

It can manufacture by attaching | subjecting the compound shown by hydrolysis reaction.

The reaction is carried out in the presence of a base or acid in the presence of water. 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 can be collected by filtration to isolate compound (7). The isolated compound (7) can be further purified by recrystallization, chromatography or the like.

〔式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴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。 (Reference production method 6)
Of compounds (7)
Formula (7-ii)

[Wherein R ¹ , R ² , R ³ , R ⁴ 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.

Specific examples of the compound of the present invention are shown below.

式中のＲ¹およびＲ³は水素を表し、Ｑは酸素を表し、Ｒ²、Ｒ⁵、Ｇ¹およびＲ⁶は、〔表１〕〜〔表３〕に記載の組合せを表す。 Compound represented by formula (A).

In the formula, R ¹ and R ³ represent hydrogen, Q represents oxygen, and R ² , R ⁵ , G ¹ and R ⁶ represent the combinations described in [Table 1] to [Table 3].

式中のＲ¹およびＲ³は水素を表し、Ｑは酸素を表し、Ｒ²、Ｒ⁵、Ｇ¹およびＲ⁶は、〔表１〕〜〔表６〕に記載の組合せを表す。 A compound represented by formula (B).

In the formula, R ¹ and R ³ represent hydrogen, Q represents oxygen, and R ² , R ⁵ , G ¹ and R ⁶ represent the combinations described in Table 1 to Table 6.

式中のＲ¹およびＲ³は水素を表し、Ｑは酸素を表し、Ｒ²、Ｒ⁵、Ｇ¹およびＲ⁶は、〔表１〕〜〔表６〕に記載の組合せを表す。 A compound represented by formula (C).

In the formula, R ¹ and R ³ represent hydrogen, Q represents oxygen, and R ² , R ⁵ , G ¹ and R ⁶ represent the combinations described in Table 1 to Table 6.

式中のＲ¹およびＲ³は水素を表し、Ｑは酸素を表し、Ｒ²、Ｒ⁵、Ｇ¹およびＲ⁶は、〔表１〕〜〔表６〕に記載の組合せを表す。 A compound represented by formula (D).

In the formula, R ¹ and R ³ represent hydrogen, Q represents oxygen, and R ² , R ⁵ , G ¹ and R ⁶ represent the combinations described in Table 1 to Table 6.

式中のＲ¹およびＲ³は水素を表し、Ｑは酸素を表し、Ｒ²、Ｒ⁵、Ｇ¹およびＲ⁶は、〔表１〕〜〔表６〕に記載の組合せを表す。 A compound represented by formula (E).

In the formula, R ¹ and R ³ represent hydrogen, Q represents oxygen, and R ² , R ⁵ , G ¹ and R ⁶ represent the combinations described in Table 1 to Table 6.

式中のＲ¹およびＲ³は水素を表し、Ｑは酸素を表し、Ｒ²、Ｒ⁵、Ｇ¹およびＲ⁶は、〔表１〕〜〔表６〕に記載の組合せを表す。 A compound represented by formula (F).

In the formula, R ¹ and R ³ represent hydrogen, Q represents oxygen, and R ² , R ⁵ , G ¹ and R ⁶ represent the combinations described in Table 1 to Table 6.

式中のＲ¹およびＲ³は水素を表し、Ｑは酸素を表し、Ｒ²、Ｒ⁵、Ｇ¹およびＲ⁶は、〔表１〕〜〔表６〕に記載の組合せを表す。 A compound represented by formula (G).

In the formula, R ¹ and R ³ represent hydrogen, Q represents oxygen, and R ² , R ⁵ , G ¹ and R ⁶ represent the combinations described in Table 1 to Table 6.

式中のＲ¹およびＲ³は水素を表し、Ｑは硫黄を表し、Ｒ²、Ｒ⁵、Ｇ¹およびＲ⁶は、〔表１〕〜〔表６〕に記載の組合せを表す。 A compound represented by formula (H).

In the formula, R ¹ and R ³ represent hydrogen, Q represents sulfur, and R ² , R ⁵ , G ¹ and R ⁶ represent the combinations described in [Table 1] to [Table 6].

式中のＲ¹およびＲ³は水素を表し、Ｑは硫黄を表し、Ｒ²、Ｒ⁵、Ｇ¹およびＲ⁶は、〔表１〕〜〔表６〕に記載の組合せを表す。 A compound represented by formula (I).

In the formula, R ¹ and R ³ represent hydrogen, Q represents sulfur, and R ² , R ⁵ , G ¹ and R ⁶ represent the combinations described in [Table 1] to [Table 6].

式中のＲ¹およびＲ³は水素を表し、Ｑは硫黄を表し、Ｒ²、Ｒ⁵、Ｇ¹およびＲ⁶は、〔表１〕〜〔表６〕に記載の組合せを表す。 A compound represented by formula (J).

In the formula, R ¹ and R ³ represent hydrogen, Q represents sulfur, and R ² , R ⁵ , G ¹ and R ⁶ represent the combinations described in [Table 1] to [Table 6].

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

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

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

  Thrips pests: Frankliniella occidentalis, Thrips parmi, Sriptotrips dorsalis, and Thrips thrips

  Diptera: Culex (Culex pipiens pallens), Culex (Culex tritaeniorhynchus), Culex such as Culex quinquefasciatus (Culex quinquefasciatus), Aedes aegypti (Aedes aegypti), Aedes albopictus (Aedes albopictus) Aedes genus such as Anopheles sinensis (Anopheles sinensis), etc. Genus Anopheles, chironomid, housefly (Musca domestica), housefly (Muscina stabulans) and other species of houseflies, fly flies, sphagnum flies, fly flies, leaf flies, moth flies, moth flies D (Agromyza oryzae), rice Hime leafminer (Hydrellia griseola), tomato leafminer, (Liriomyza sativae), legume leafminer (Liriomyza trifolii), leafminer such as the pea (Chromatomyia horticola), chloropidae such as Inekimoguribae (Chlorops oryzae), melon fly (Dacus cucurbitae), fruit flies such as Ceratitis capitata, fruit flies such as Drosophila, flea flies, Megasaria sp., And the like. Abu acids, and stable flies such as gadfly (Tabanus trigonus).

Coleoptera pests: Western Corn Rootworm (Diabrotica virgifera virgifera), corn rootworm such as southern corn rootworm (Diabrotica undecimpunctata howardi), cupreous chafer (Anomala cuprea), rufocuprea (Anomala rufocuprea), chafers such as Japanese beetle (Popillia japonica) , Weevil (Sitophilus zeamais), Rice weevil (Lissorhoptrus oryzophilus), Azuki beetle (Callosobruchuys chiensis), Echonocnemus squatium (Echinocnemus squat) onomus grandis), weevils such as grass reed weevil (Sphenophorus venatus), Chai Loco Meno mealworm (Tenebrio molitor), mealworm such as red flour beetle (Tribolium castaneum),
Inedorooimushi (Oulema oryzae), cucurbit leaf beetle (Aulacophora femoralis), Kisujinomihamushi (Phyllotreta striolata), beetles such as Colorado potato beetle (Leptinotarsa decemlineata), varied carpet beetle (Anthrenus verbasci), carpet beetle such as Hara Giro beetle (Dermestes maculates), cigarette beetle (Lasiderma serricorne) and the like, Epilachna vigintioctopuncta and other epilacunas, Lyctus brunneus and pine beetle (Pompicus) erda), bark beetles, leopard beetles, longhorn beetles (Anoprophora malasiaca), longhorn beetles (Agriotes spp.), and blue scallops (ed) p.

  Pterodoptera: Tocusama grasshopper (Locusta migratoria), Kera (Gryllotalpa africana), Oxya yezoensis, Oyana japonica, Oroja japonica, etc.

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

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

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

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

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

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

  Examples of the liquid carrier include water, alcohols (methanol, ethanol, isopropyl alcohol, butanol, hexanol, benzyl alcohol, ethylene glycol, propylene glycol, phenoxyethanol, etc.), ketones (acetone, methyl ethyl ketone, cyclohexanone, etc.), aromatic hydrocarbons (Toluene, xylene, ethylbenzene, dodecylbenzene, phenylxylylethane, methylnaphthalene, etc.), aliphatic hydrocarbons (hexane, cyclohexane, kerosene, light oil, etc.), esters (ethyl acetate, butyl acetate, isopropyl myristate, Ethyl oleate, diisopropyl adipate, diisobutyl adipate, propylene glycol monomethyl ether acetate, etc.), nitriles (acetonitrile, isobutyro Tolyl), ethers (diisopropyl ether, 1,4-dioxane, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether, 3-methoxy-3-methyl-1-butanol, etc. ), Acid amides (N, N-dimethylformamide, N, N-dimethylacetamide, etc.), halogenated hydrocarbons (dichloromethane, trichloroethane, carbon tetrachloride, etc.), sulfoxides (dimethylsulfoxide, etc.), propylene carbonate and vegetable oil (Soybean oil, cottonseed oil, etc.).

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

  Examples of the surfactant include nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, 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).

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

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

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

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

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

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

  “Crop” also includes genetically modified crops.

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

〔式中、
Ｒ₁は塩素、臭素またはトリフルオロメチル基を表し、
Ｒ₂は塩素、臭素またはメチル基を表し、
Ｒ₃は塩素、臭素またはシアノ基を表す。〕
で示される化合物、及び
下記式（Ｌ）

〔式中、
Ｒ₁は塩素、臭素またはヨウ素を表す。〕
で示される化合物。 Active Ingredients of Insecticides (1) Organophosphorus Compounds Acephate, Aluminum Phosphide, Butathiofos, Cadosafos, Chlorethoxyfos, Chlorfenvinphos, Chlorfenvinphos (Chlorpyrifos), Chlorpyrifos-methyl (Chlorpyrifos-methyl), Cyanophos (Cyanophos: CYAP), Diazinon (Diazinon), DCIP (Dichlorodiisopropylene ether), Diclofenthion (V: D) ), Dimethoate, dimethylvinphos, disulfoton, EPN, etion, ethoprofos, etrimfos, fenthion: MPP, fethion: MPP Phosthiazate, formothion, hydrogen phosphide, isofenphos, isoxathion, malathion, methulfenfos, methulfenfos, methulfenfos MTP), monocrotophos, nared (BRP), oxydeprofos (ESP), parathion, fosarone, phosmet (PMP), pirimiphosmethyl (pirimithiopimethiopimethiopimethiopimethiopimethiopimethiopimethiopimethypisonepimethypisonepimethypisonepimethypisonepimethypisonepimethypisonepimethypisonepimethypisonepimethypisone (Pyridafenthion), quinalphos, phentoate (PAP), profenofos, propopafos, prothiofos, pyrachlorfos, prothiouls, prothion Tebupirimfos, temefos, tetrachlorbinphos (tetrach1orvinphos), terbufos, thiomethon, trichlorfon (DEP), bamidithios (vamidothionate, vamidothionate) .
(2) Carbamate compounds alaniccarb, bendiocarb, benfuracarb, BPMC, carbaryl (carbary1), carbofuran, carbothofen, loecarb , Fenobucarb, phenothiocarb, phenoxycarb, furatiocarb, isoprocarb (MIPC), methocarb (metolcarb) hiocarb, NAC, oxamyl, pirimiccarb, propoxur (PHC), XMC, thiodicarb, xylylcarb, and aldicarb.
(3) Pyrethroid compounds acrinathrin, allethrin, benfluthrin, beta-cyfluthrin, bifenthrin, cycloprotorin, fluprothrin , Cypermethrin, deltamethrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucitrate lucytrinate, flufenprox, flumethrin, fluvalinate, halfenprox, imiprothrin, permethrin, praretrin, praretrin resmethrin), sigma-cypermethrin, silafluofen, tefluthrin, tralomethrin, transfluthrin, tetramethrin. ethrin, phenothrin, cyphenothrin, alpha-permethrin, zeta-cypermethrin, lambda cihalothrin (lambda-halothrin) ), Furamethrin, tau-fluvalinate, methfluthrin, profluthrin, dimethylfluthrin, 2,3,5,6-tetrafluoro-4- (methoxymethyl) benzyl EZ)-(1RS, 3RS; 1RS, 3S R) -2,2-dimethyl-3-prop-1-enylcyclopropanecarboxylate, 2,3,5,6-tetrafluoro-4-methylbenzyl (EZ)-(1RS, 3RS; 1RS, 3SR)- 2,2-dimethyl-3-prop-1-enylcyclopropanecarboxylate and 2,3,5,6-tetrafluoro-4- (methoxymethyl) benzyl (1RS, 3RS; 1RS, 3SR) -2,2 -Dimethyl-3- (2-methyl-1-propenyl) cyclopropanecarboxylate.
(4) Nereistoxin compound Cartap, bensultap, thiocyclam, monosultap, bisultap.
(5) Neonicotinoid compounds imidacloprid (imidac1oprid), nitenpyram (nitenpyram), acetamiprid (acetamipride), thiamethoxam, thiacloprid (thiacloprid), dinoteurine (dinocurin)
(6) Benzoylurea compounds Chlorfluazuron, bistrifluron, diafenthiuron, diflubenzuron, fluazuron, flucyclolone, flucyclolone (Flufenoxuron), hexaflumuron, lufenuron, novaluron, novifluuron, teflubenzuron, triflumuron, and triflumuron.
(7) Phenylpyrazole compounds Acetoprole, etiprole, fipronil, vaniliprole, pyriprole, and pyrafluprole.
(8) Bt toxin insecticide Live spores and produced crystal toxins derived from Bacillus thuringiensis, and mixtures thereof.
(9) Hydrazine compounds Chromafenozide, halofenozide, methoxyphenozide, and tebufenozide.
(10) Organochlorine compounds Aldrin, dieldrin, dienochlor, endosulfan, and methoxychlor.
(11) Other insecticide active ingredients Machine oil (nicotine-sulfate); avermectin (avermectin-B), bromopropyrate, buprofezin, chlorphenapyr Ritranol, cyromazine, DD (1,3-Dichloropropene), emamectin benzoate, fenazaquin, flupyrazolene, flupyrazolene Indoxacarb, methoxadiazone, milbemycin-A, pymetrozine, pyridalyl, lurapyruto, finoprodyl ), Triazemate, flubendiamide, repimectin, arsenous acid, benclothiaz, lime nitrogen (Calcium cynamide), lime sulfur compound lfide), chlordane, DDT, DSP, flufenerim, flonicamid, flurimfen, formatenate, metham-ammonium, metam-ammonium sodium, methyl bromide, potassium oleate, protrifenbute, spiromesifen, sulfoxafluor, sulfur, metafluon, sulfur ), Spirotetramat (spi) otetramat), pyrifluquinazon (pyrifluquinazone), spinetoram (spinetoram), chlorantraniliprole (chlorantraniliprole), Toraropiriru (tralopyril), cyan tiger Niri Prowl (cyantraniliprole),
Following formula (K)

[Where,
R ₁ represents chlorine, bromine or trifluoromethyl group;
R ₂ represents chlorine, bromine or methyl group;
R ₃ represents chlorine, bromine or a cyano group. ]
And a compound represented by the following formula (L)

[Where,
R ₁ represents chlorine, bromine or iodine. ]
A compound represented by

Active ingredients of acaricides: acequinocyl, amitraz, benzoximate, bifenaate, phenisobromolate, chinomethionate BS, chloromethionate BS chlorfenson, clofentezine, cyflumetofene, kelsen (dicofol), etoxazole, fenbutatin oxide, fenothiocarbene roximate, fluacrylpyrim, fluproxyfen, hexythiazox, propargite (BPPS), polynactin complex (pyridene), pyridaben (pyriben) (Teradifoun), spirodiclofen, spiromesifen, spirotetramat, amideflumet, and cenopyrafen.

Active ingredients of nematicides DCIP, fostiazate, levamisole hydrochloride, methylisothiocyanate, morantel tartrate, and imiciafos.

Antibacterial active ingredients propiconazole, prothioconazole, triadimenol, prochloraz, penconazole, tebuconazole, tebuconazole, tebuconazole, tebuconazole , Bromuconazole, epoxiconazole, difenoconazole, cyproconazole, metconazole, triflumazole, triflumizole Tetraconazole, microbutanil, fenbuconazole, hexaconazole, fluquinconazole, triticonazole, triticonazole, triticonazole, triticonazole, triticonazole, triticonazole Azole fungicidal compounds such as flutriafol;
Cyclic amine bactericidal compounds such as fenpropimorph, tridemorph, fenpropidin;
Benzimidazolic fungicidal compounds such as carbendezim, benomyl, thiabendazole, thiophanate-methyl;
Procymidone; cyprodinil; pyrimethanil; dietofencarb; thiuram; fluazilonyl; Captan; mepanipyrim; fenpiclonil; fludioxonil; dicloflulanid; folppet; cresoxime- azoxystrobin; trifloxystrobin; fluoxastrobin; picoxystrobin; pyracrostrobin; dimoxystrobin; dimoxystrobin; dimoxystrobin; Pyribencarb; spiroxamine; quinoxyfen; fenhexamid; famoxadone; fenamidone; samamide; samamide; iprovalicarb; benthiavaricarb; cyazofamid; mandipropamid; boscaliden; (Bixafen); cyflufenamide; proquinazid; isotianil and thiadinil.

Active ingredient of herbicide (1) Phenoxy fatty acid herbicidal compound 2,4-PA, MCP, MCPB, phenthiol (phenothio1), mecoprop, fluroxypyr, triclopyr, clomeprop, and clomeprop Naproanilide.
(2) Benzoic acid herbicidal compound 2,3,6-TBA, dicamba, clopyralid, picloram, aminopyralid, quinclorac, and quinmerac.
(3) Urea herbicidal compounds diuron, linuron, chlortoluron, isoproturon, fluometuron, isouron, tebuthiuron, tebuthiuron, metabenthuron , Cumyluron, daimuron, and methyl-daimuron.
(4) Triazine herbicidal compounds atrazine, ametrine, cyanazine, simazine, propazine, simetrin, dimetamethrin (dimetrimetrin) ), Triaziflam, and indaziflam.
(5) Bipyridinium herbicidal compound paraquat and diquat.
(6) Hydroxybenzonitrile herbicidal compounds bromoxynil, ioxynil.
(7) Dinitroaniline herbicidal compound pendimethalin, prodiamine, and trifluralin.
(8) Organophosphorus herbicidal compounds amiprofos-methyl, butamifos, bensulide, piperophos, anilofos, glyphosate, glufosinate, glufosinate, glufosinate P (glufosinate-P), and bialaphos.
(9) Carbamate herbicidal compounds di-allate, tri-allate, EPTC, butyrate, beniocarb, esprocarb, molinate, dimepiperate (Swep), chlorpropham, phenmedifam, phenisopham, piributicalb, and asuram.
(10) Acid amide herbicidal compounds propanil, propyzamide, bromobutide, and etobenzanide.
(11) Chloroacetanilide herbicidal compounds acetochlor, acechlor, butachlor, dimethenamide, propachlor, metazachlor, metrachlor, pretrachlor pretilachor), tenylchlor (theny1ch1or), and petoxamide.
(12) Diphenyl ether herbicidal compounds aciflufen-sodium, bifenox, oxyfluorfen, lactofen, fomesafen, clomethoxythonifen, and clomethoxythonipheni.
(13) Cyclic imide herbicidal compounds oxadiazon, cinidon-ethyl, carfentrazone-ethyl, sulfentrazone, full-microlac-pentyl, flumi-lacyl-pentyl Oxazine (flumioxazin), pyraflufen-ethyl, oxadiargyl (oxadiargyl), pentoxazone (pentoxazone), fluthiacet-methyl (butafenzilben) zone), and saflufenacil (saflufenacil).
(14) Pyrazole herbicidal compounds benzofenap, pyrazolate, pyrazoxifene, topramzone, and pyrasulfotole.
(15) Triketone herbicidal compounds isoxaflutole, benzobicyclon, sulcotrione, mesotrione, tembotrione, and tefriltrione.
(16) Aryloxyphenoxypropionic acid herbicidal compound clodinafop-propargyl, cyhalofop-butyl, diclohop-methyl, phenoxaprop-ethyl, fenoxaprop-propyl Fluazifop-butyl, haloxyhop-methyl, quizalofop-ethyl, and metamihop.
(17) Trione oxime herbicidal compounds alloxydim-sodium, cetoxydim, butroxydim, crestodim, cloproxidim, cyclohexyloxym (Traxydim), and profoxidim.
(18) sulfonylurea herbicidal compounds chlorsulfuron, sulfomethuron-methyl, metsulfuron-methyl, chlorimuron-ethyl, trivenuron methyl (18) tribenuron-methyl, triasulfuron, bensulfuron-methyl, thifensulfuron-methyl, pyrazosulfuron-methyl, urmisyl Nicosulfuron (nico) ulfuron, amidosulfuron, cinosulfuron, imazosulfuron, rimsulfuron, halosulfuron (th), thulfuron (thulsulfuron), prosulfuron (thulsulfuron) , Triflusulfuron-methyl, flazasulfuron, cyclosulfamuron, flupirsulfuron, sulfosulfurium, sulfosulfurium Azulsulfuron, ethoxysulfuron, oxasulfuron, iodosulfuron-methyl-sodium, foramsulfuron, mesosulfuron, mesulfuron methyl Trisulfoxysulfuron, tritosulfuron, orthosulfamuron, flucetosulfuron, and propyrisulfuron.
(19) Imidazolinone herbicidal compounds imazametabenz-methyl, imazametapyr, imazamox, imazapyr, and imazaquin (p), imazapyr and imazaquin (p)
(20) Sulfonamide herbicidal compounds flumetslam, metosulam, dicloslam, florasulam, chloranthrammethyl, penoxsulox, penoxsulox, and penoxsulox.
(21) Pyrimidinyloxybenzoic acid herbicidal compound pyrithiobac-sodium, bispyribac-sodium, pyriminobac-methy1, pyribenzoximid, pyrifalidomid And pyrimisulfan.
(22) Other herbicidal compounds bentazone, bromacil, terbacil, chlorthiamid, isoxaben, dinoseb, amitrol, cinmethyline, cinmethyline (cinthyl) tripiphane, dalapon (da1apon), diflufenzopyr sodium (diflufenzopyr-sodium), dithiopyr (dithiopyr), thiazopyr (thiazopyr), sodium flucarbazone (profluzazone) Nasset (mefenacet), flufenacet (flufenacet), fentrazamide (fentrazamide), caffenstrole (cafenstrom), indanophan (indanofan), oxadichromemephone (oxaneclomefone), fidarate (benduresate) (Norflurazon), flurtamon, diflufenican, picolinafene, beflubutamid, clomazone, amicarbazone , Pinoxaden (pinoxaden), pyraclonil (pyraclonil), pyroxasulfone (pyroxasulfone), thien-carbazone methyl (thiencarbazone-methyl), amino cyclo Pila crawl (aminocyclopyrachlor), type phen carbazone (ipfencarbazone), and Mechiozorin (methiozolin).

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

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

  First, the manufacture example of this invention compound is shown below. In the production examples, Ph represents a phenyl group, and 2-ClPh represents a 2-chlorophenyl group.

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〈化合物４４〉

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 then 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 <Compound 44>

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〈化合物７７〉

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 <Compound 77>

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〈化合物８３〉

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-hexafluorobutyroxy) -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 <Compound 83>

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〈化合物８７〉

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 <Compound 87>

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〈化合物９０〉

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〈化合物８９〉

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 give 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 to give 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 <Compound 90>

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 10% Pd / C mixture 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 <Compound 89>

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〈化合物９１〉

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. The solid was washed with acetonitrile and 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 5-methyl-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine, 4 mL 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-hexafluorobutyoxy) -5-methyl-6-[[1,2,4] triazol-1-yl ) -Pyrimidine 0.50 g was obtained.
4- (2,2,3,4,4,4-Hexafluorobutyoxy) -5-methyl-6-[[1,2,4] triazol-1-yl) -pyrimidine <Compound 91>

Compound 91 was synthesized by the following production method (Production Example 6-1 and Production Example 6-2).

^１Ｈ−ＮＭＲ（ＣＤＣｌ_３）δ：２．２９（３Ｈ，ｓ），４．７４−４．８７（２Ｈ，ｍ），４．９２−５．１５（１Ｈ，ｍ），８．４６（１Ｈ，ｓ）．
４−クロロ−６−（２，２，３，４，４，４−ヘキサフルオロブチロキシ）−５−メチルピリミジン０．６２ｇ、１，２，４−トリアゾール０．１５ｇ、ＤＢＵ０．３５ｇおよびＮＭＰ３ｍＬの混合物を５０℃で１時間攪拌し、１００℃で１時間および１３０℃で６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−（２，２，３，４，４，４−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０．３３ｇを得た。＜化合物９１＞ Production Example 6-1
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).
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. <Compound 91>

^１Ｈ−ＮＭＲ（ＣＤＣｌ_３）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。＜化合物９１＞ Production Example 6-2
A mixture of 3.26 g of 4,6-dichloro-5-methylpyrimidine and 30 mL of tetrahydrofuran was ice-cooled, 2.02 g of sodium 1,2,4-triazole 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. <Compound 91>

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〈化合物１０２〉

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 hand solids. 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).
0.44 g of 5-bromo-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine, 3 mL of NMP 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 <Compound 102>

¹Ｈ−ＮＭＲ（ＤＭＳＯ−Ｄ₆）δ：２．７５（３Ｈ，ｓ），７．９５（１Ｈ，ｓ），８．４７（２Ｈ，ｓ），９．５６（２Ｈ，ｓ）．
２−メチル−４，６−ビス（［１，２，４］トリアゾール−１−イル）−ピリミジン０．３４ｇ、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。この混合物を６０℃で０．５時間攪拌した。放冷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）−２−メチル−６−（［１，２，４］トリアゾール−１−イル）−ピリミジン０．２６ｇを得た。
４−（２，２，３，４，４，４−ヘキサフルオロブチロキシ）−２−メチル−６−（［１，２，４］トリアゾール−１−イル）−ピリミジン〈化合物１０６〉

Production Example 8
To a mixture of 27.6 g of 1,2,4-triazole, 50 mL of acetonitrile and 51.7 g of N-ethyldiisopropylamine, 16.3 g of 4,6-dichloro-2-methylpyrimidine was added at room temperature. The mixture was heated to reflux for 14 hours. The reaction mixture was filtered to collect the solid. The solid was washed with acetonitrile and dried to obtain 20.3 g of 2-methyl-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine.
2-Methyl-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine

¹ H-NMR (DMSO-D ₆ ) δ: 2.75 (3H, s), 7.95 (1H, s), 8.47 (2H, s), 9.56 (2H, s).
2-methyl-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine 0.34 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. The mixture was stirred at 60 ° C. for 0.5 hour. An aqueous citric acid solution was poured into the reaction mixture which had been allowed to cool, 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) -2-methyl-6-[[1,2,4] triazol-1-yl ) -Pyrimidine (0.26 g) was obtained.
4- (2,2,3,4,4,4-Hexafluorobutyoxy) -2-methyl-6-([1,2,4] triazol-1-yl) -pyrimidine <Compound 106>

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〈化合物１１２〉

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 <Compound 112>

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〈化合物１１６〉

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 obtain 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-hexafluorobutyroxy) -6-([1,2,4] triazol-1-yl) -pyrimidine <Compound 116>

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〈化合物１２４〉

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 was added 0.51 g DBU 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 <Compound 124>

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〈化合物１２９〉

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-hexafluorobutyoxy) -6-([1,2,4] triazol-1-yl) -pyrimidine <Compound 129>

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〈化合物１５２〉

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 <Compound 152>

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〈化合物１５６〉

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 <Compound 156>

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：７．１６−７．１８（２Ｈ，ｍ），７．４０−７．５０（３Ｈ，ｍ），７．９１（２Ｈ，ｓ），８．５４（２Ｈ，ｓ），９．１６（１Ｈ，ｓ）．
５−フェニル−４，６−ビス（［１，２，４］トリアゾール−１−イル）−ピリミジン０．２９ｇ、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）−５−フェニル−６−（［１，２，４］トリアゾール−１−イル）−ピリミジン０．２６ｇを得た。
４−（２，２，３，４，４，４−ヘキサフルオロブチロキシ）−５−フェニル−６−（［１，２，４］トリアゾール−１−イル）−ピリミジン〈化合物１６１〉

Production Example 15
To a mixture of 3.32, g of 1,2,4-triazole, 10 mL of acetonitrile and 4.50 g of 4,6-dichloro-5-phenylpyrimidine, 6.20 g of N-ethyldiisopropylamine was added at room temperature. The mixture was heated to reflux for 13 hours. The reaction mixture was allowed to cool to room temperature and the solid was collected by filtration. The solid was washed with acetonitrile and dried to obtain 4.72 g of 5-phenyl-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine.
5-Phenyl-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine

¹ H-NMR (CDCl ₃ ) δ: 7.16-7.18 (2H, m), 7.40-7.50 (3H, m), 7.91 (2H, s), 8.54 (2H , S), 9.16 (1H, s).
5-phenyl-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine 0.29 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 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, and 4- (2,2,3,4,4,4-hexafluorobutyroxy) -5-phenyl-6-[[1,2,4] triazol-1-yl ) -Pyrimidine (0.26 g) was obtained.
4- (2,2,3,4,4,4-Hexafluorobutyoxy) -5-phenyl-6-([1,2,4] triazol-1-yl) -pyrimidine <Compound 161>

^１Ｈ−ＮＭＲ（ＣＤＣｌ_３）δ：７．１２−７．１４（１Ｈ，ｍ），７．２７−７．２９（１Ｈ，ｍ），７．３９−７．４６（２Ｈ，ｍ），７．８６（２Ｈ，ｓ），８．９０（２Ｈ，ｓ），９．１３（１Ｈ，ｓ）．
５−（２−クロロフェニル）−４，６−ビス（［１，２，４］トリアゾール−１−イル）−ピリミジン０．３２ｇ、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、５−（２−クロロフェニル）−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０．３２ｇを得た。
５−（２−クロロフェニル）−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〈化合物１６３〉

Production Example 16
A mixture of 1.16 g of 1,2,4-triazole, 5 mL of acetonitrile and 1.81 g of 5- (2-chlorophenyl) -4,6-dichloropyrimidine was ice-cooled, and 2.56 g of DBU was added. The mixture was stirred at room temperature for 0.5 hours. The reaction mixture was filtered to collect hand solids. This solid was washed with acetonitrile and then dried to obtain 1.46 g of 5- (2-chlorophenyl) -4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine.
5- (2-Chlorophenyl) -4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine

¹ H-NMR (CDCl ₃ ) δ: 7.12-7.14 (1H, m), 7.27-7.29 (1H, m), 7.39-7.46 (2H, m), 7 .86 (2H, s), 8.90 (2H, s), 9.13 (1H, s).
5- (2-Chlorophenyl) -4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine 0.32 g, NMP 2 mL and 2,2,3,4,4,4-hexafluoro- To a mixture of 0.18 g of 1-butanol, 0.15 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- (2-chlorophenyl) -4- (2,2,3,4,4,4-hexafluorobutyroxy) -6-([1,2,4] triazole -1-yl) -pyrimidine (0.32 g) was obtained.
5- (2-Chlorophenyl) -4- (2,2,3,4,4,4-hexafluorobutyroxy) -6-([1,2,4] triazol-1-yl) -pyrimidine <Compound 163 >

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〈化合物１６５〉

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 <Compound 165>

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〈化合物１６７〉

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 then 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 <Compound 167>

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〈化合物１６９〉

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 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 <Compound 169>

¹Ｈ−ＮＭＲ（ＤＭＳＯ−Ｄ₆）δ：７．０１（１Ｈ，ｓ），７．６０（２Ｈ，ｂｒｓ），８．３７（１Ｈ，ｓ），９．２０（１Ｈ，ｓ）．
２−アミノ−４−クロロ−６−（［１，２，４］トリアゾール−１−イル）−ピリミジン０．９８ｇ、ＮＭＰ５ｍＬ及び２，２，３，４，４，４−ヘキサフルオロ−１−ブタノール０．９１ｇの混合物に、室温で６０％水素化ナトリウム（油性）０．２４ｇを加えた。この混合物を９０℃で３時間攪拌した。放冷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、２−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０．１１ｇを得た。
２−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〈化合物１９０〉

Production Example 20
To a mixture of 8.29 g of 1,2,4-triazole, 25 mL of acetonitrile and 15.5 g of N-ethyldiisopropylamine, 8.20 g of 2-amino-4,6-dichloropyrimidine was added at room temperature. The mixture was heated to reflux for 6 hours. The reaction mixture was cooled to room temperature. The reaction mixture was filtered to collect the solid. This solid was washed successively with acetonitrile and tetrahydrofuran and dried to obtain 3.86 g of 2-amino-4-chloro-6-[[1,2,4] triazol-1-yl) -pyrimidine.
2-Amino-4-chloro-6-[[1,2,4] triazol-1-yl) -pyrimidine

¹ H-NMR (DMSO-D ₆ ) δ: 7.01 (1H, s), 7.60 (2H, brs), 8.37 (1H, s), 9.20 (1H, s).
2-Amino-4-chloro-6-[[1,2,4] triazol-1-yl) -pyrimidine 0.98 g, NMP 5 mL and 2,2,3,4,4,4-hexafluoro-1-butanol To 0.91 g of the mixture was added 0.24 g of 60% sodium hydride (oil) at room temperature. The mixture was stirred at 90 ° C. for 3 hours. An aqueous citric acid solution was poured into the reaction mixture which had been allowed to cool, 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 2-amino-4- (2,2,3,4,4,4-hexafluorobutyroxy) -6-[[1,2,4] triazol-1-yl. ) -Pyrimidine (0.11 g) was obtained.
2-Amino-4- (2,2,3,4,4,4-hexafluorobutyroxy) -6-([1,2,4] triazol-1-yl) -pyrimidine <Compound 190>

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〈化合物１９１〉

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０．５５ｇ及びクロロホルム５ｍＬの混合物に氷冷下でｍ−クロロ過安息香酸０．４９ｇを加えた。この混合物を室温で一晩攪拌した。反応混合物に炭酸水素ナトリウム水溶液を注加し、酢酸エチルで抽出した。有機層を水洗した後、硫酸ナトリウムで乾燥し、減圧下に濃縮した。残渣をヘキサン及びｔ−ブチルメチルエーテルの混合溶媒（２：１）で洗浄し、４−（２，２，３，４，４，４−ヘキサフルオロブチル−１−スルフィニル）−６−（［１，２，４］トリアゾール−１−イル）−ピリミジン０．４２ｇを得た。
４−（２，２，３，４，４，４−ヘキサフルオロブチル−１−スルフィニル）−６−（［１，２，４］トリアゾール−１−イル）−ピリミジン〈化合物１９２〉

４−（２，２，３，４，４，４−ヘキサフルオロブチル−１−スルフィニル）−６−（［１，２，４］トリアゾール−１−イル）−ピリミジン０．３０ｇ及びクロロホルム５ｍＬの混合物に、ｍ−クロロ過安息香酸０．２５ｇを加えた。この混合物を６０℃で８時間攪拌した。放冷した反応混合物に炭酸水素ナトリウム水溶液を注加し、酢酸エチルで抽出した。有機層を水洗した後、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−スルホニル）−６−（［１，２，４］トリアゾール−１−イル）−ピリミジン０．１８ｇを得た。
４−（２，２，３，４，４，４−ヘキサフルオロブチル−１−スルホニル）−６−（［１，２，４］トリアゾール−１−イル）−ピリミジン〈化合物１９３〉

Production Example 21
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 <Compound 191>

A mixture of 0.55 g of 4- (2,2,3,4,4,4-hexafluorobutyl-1-sulfanyl) -6-([1,2,4] triazol-1-yl) -pyrimidine and 5 mL of chloroform To the solution, 0.49 g of m-chloroperbenzoic acid was added under ice cooling. The mixture was stirred overnight at room temperature. An aqueous sodium hydrogen carbonate solution was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate, and concentrated under reduced pressure. The residue was washed with a mixed solvent of hexane and t-butyl methyl ether (2: 1) to give 4- (2,2,3,4,4,4-hexafluorobutyl-1-sulfinyl) -6-([1 , 2,4] triazol-1-yl) -pyrimidine 0.42 g was obtained.
4- (2,2,3,4,4,4-Hexafluorobutyl-1-sulfinyl) -6-([1,2,4] triazol-1-yl) -pyrimidine <Compound 192>

4- (2,2,3,4,4,4-hexafluorobutyl-1-sulfinyl) -6-([1,2,4] triazol-1-yl) -pyrimidine (0.30 g) and chloroform (5 mL) 0.25 g of m-chloroperbenzoic acid was added. The mixture was stirred at 60 ° C. for 8 hours. An aqueous sodium hydrogen carbonate solution was poured into the cooled reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 4- (2,2,3,4,4,4-hexafluorobutyl-1-sulfonyl) -6-[[1,2,4] triazol-1-yl). -0.18 g of pyrimidine was obtained.
4- (2,2,3,4,4,4-Hexafluorobutyl-1-sulfonyl) -6-([1,2,4] triazol-1-yl) -pyrimidine <Compound 193>

Production Example 22
To a mixture of 0.23 g of 4,6-di (imidazol-1-yl) -5-methylpyrimidine, 2 mL of NMP and 0.10 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 <Compound 195>

Production Example 23
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) was added 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 <Compound 196>

^１Ｈ−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）．
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−Ｄ_６）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＜化合物１９７＞

Production Example 24
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 5.84 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 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) -pyrimidine-4-thiol 0.19 g, N, N-dimethylformamide 1 mL and trifluoromethanesulfonic acid 2,2,3,4, To a mixture of 4,1-hexafluoro-1-butyl 0.31 g, potassium carbonate 0.17 g 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 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 <Compound 197>

Production Example 25
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 <Compound 198>

Production Example 26
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 <Compound 222>

Production Example 27
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 <Compound 219>

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、ＮＭＰ３ｍＬ及び２，２，２，４，４−ペンタフルオロ−１，３−ブタンジオール０．３６ｇの混合物に氷冷下で、ＤＢＵ０．４０ｇ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、酢酸エチルで抽出した。有機層を飽和塩化アンモニウム水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−（３−ヒドロキシ−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０．３０ｇを得た。
４−（３−ヒドロキシ−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＜化合物２２６＞

Production Example 28
Under a nitrogen atmosphere, 84 mL of butyl lithium (1.6 M) was added to a mixture of 10.9 g of 1,1,1,3,3,3-hexafluoro-2-propanol and 50 mL of tetrahydrofuran under ice cooling. The mixture was stirred for 2 hours under ice cooling. Next, 19.5 g of paraformaldehyde was added to the mixture, and the mixture was stirred at room temperature for 10 hours. To the reaction mixture, 100 mL of water and 3.7 g of sodium borohydride were added. The mixture was stirred at room temperature for 1 day. 20% hydrochloric acid (20 mL) was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was concentrated under reduced pressure. The residue was distilled under reduced pressure to obtain 7 g of 2,2,2,4,4-pentafluoro-1,3-butanediol.
2,2,2,4,4-pentafluoro-1,3-butanediol

0.46 g of 5-methyl-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine, 3 mL of NMP and 2,2,2,4,4-pentafluoro-1,3-butanediol To 0.36 g of the mixture, 0.40 g of DBU was added under ice cooling. The mixture was stirred at room temperature for 5 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 to give 4- (3-hydroxy-2,2,4,4,4-pentafluorobutyroxy) -5-methyl-6-[[1,2,4] triazole-1 0.30 g of -yl) -pyrimidine was obtained.
4- (3-Hydroxy-2,2,4,4,4-pentafluorobutyoxy) -5-methyl-6-[[1,2,4] triazol-1-yl) -pyrimidine <Compound 226>

Production Example 29
4- (3-Hydroxy-2,2,4,4,4-pentafluorobutyroxy) -5-methyl-6-[[1,2,4] triazol-1-yl) -pyrimidine 0.17 g and tetrahydrofuran To 3 mL of the mixture, 0.03 g of sodium hydride (60% oily) and 0.08 g of methyl iodide were added under ice cooling. 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 to give 4- (2,2,4,4,4-pentafluoro-3-methoxy-butyroxy) -5-methyl-6-[[1,2, 4] 0.18 g of triazol-1-yl) -pyrimidine was obtained. <Compound 227>

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＜化合物２２８＞

Production Example 30
4- (3-Hydroxy-2,2,4,4,4-pentafluorobutyroxy) -5-methyl-6-[[1,2,4] triazol-1-yl) -pyrimidine 0.68 g and tetrahydrofuran To 3 mL of the mixture, 0.03 g of sodium hydride (60% oily) and 0.38 g of phenyl chlorothiocarbonate were added under ice cooling. 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-pentafluorobutyoxy) -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 <Compound 228>

^１Ｈ−ＮＭＲ（ＣＤＣｌ_３）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。＜化合物１１＞

Production Example 31
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 0.18 g of 4-([1,2,4] triazol-1-yl) -6- [2,2-bis (trifluoromethyl) propoxy] -pyrimidine. Got. <Compound 11>

^１Ｈ−ＮＭＲ（ＣＤＣｌ_３）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。＜化合物２２＞

Production Example 32
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. <Compound 22>

Compound 22 was synthesized by the following production method (Production Example 32-1).

Production Example 32-1
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 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. <Compound 22>

Production Example 33
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 <compound 121 >

Production Example 34
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 <compound 133 >

Production Example 35
To a mixture of 0.46 g of 5-methyl-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine, 3 mL of NMP and 0.25 g of ethylene glycol mono-tert-butyl ether, add 0.33 g of DBU. 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 0.68 g of 5-methyl-4- (2-tert-butoxyethoxy) -6-([1,2,4] triazol-1-yl) -pyrimidine. Obtained.
5-Methyl-4- (2-tert-butoxyethoxy) -6-([1,2,4] triazol-1-yl) -pyrimidine <Compound 135>

式中のＲ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ｇ¹、Ｒ⁶およびＱは、下記の〔表７〕〜〔表１４〕に記載の組合せを表す。 Hereinafter, the compound manufactured by the manufacturing method according to the method as described in the above-mentioned Example manufacture example is illustrated.

R ¹ , R ² , R ³ , R ⁴ , R ⁵ , G ¹ , R ⁶ and Q in the formula represent the combinations described in the following [Table 7] to [Table 14].

¹ H-NMR data of the compounds of the present invention described in [Table 7] to [Table 17] are shown below.

Compound 1
¹ H-NMR (CDCl ₃ ) δ: 2.23 (3H, s), 2.91 (2H, t), 4.64 (2H, t), 7.24 (1H, d), 8.12 ( 1H, s), 8.65 (1H, d), 9.18 (1H, s).
Compound 2
¹ H-NMR (CDCl ₃ ) δ: 1.00 (3H, t), 1.41 (6H, s), 1.53-1.65 (2H, m), 2.60 (2H, t), 4.41 (2H, s), 7.27 (1H, d), 8.12 (1H, s), 8.64 (1H, d), 9.18 (1H, s).
Compound 3
¹ H-NMR (CDCl ₃ ) δ: 1.40 (6H, s), 2.12-2.14 (3H, m), 4.41 (2H, s), 7.27 (1H, s), 8.12 (1H, s), 8.64 (1H, s), 9.18 (1H, s).
Compound 5
¹ H-NMR (CDCl ₃ ) δ: 1.54 (6H, s), 3.02 (3H, s), 4.69 (2H, s), 7.26 (1H, s), 8.13 ( 1H, s), 8.69 (1H, s), 9.20 (1H, s).
Compound 6
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).
Compound 7
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).
Compound 8
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).
Compound 9
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).
Compound 10
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).
Compound 11
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).
Compound 12
¹ H-NMR (CDCl ₃ ) δ: 1.65 to 1.82 (3H, m), 1.87 to 1.89 (2H, m), 3.28 (2H, t), 3.74 (2H , S), 7.71 (1H, d), 8.12 (1H, s), 8.79 (1H, d), 9.20 (1H, s).
Compound 13
¹ H-NMR (CDCl ₃ ) δ: 1.25 (6H, s), 2.00-2.04 (2H, m), 3.24 (3H, s), 4.53-4.57 (2H M), 7.19 (1H, d), 8.12 (1H, s), 8.65 (1H, d), 9.18 (1H, s).
Compound 14
¹ H-NMR (CDCl ₃ ) δ: 1.25 (6H, s), 1.99-2.03 (2H, m), 3.24 (3H, s), 4.52-4.56 (2H M), 6.63 (1H, d), 7.20-7.21 (1H, m), 7.60-7.61 (1H, m), 8.41-8.42 (1H, m). ), 8.65 (1H, d).
Compound 15
¹ H-NMR (CDCl ₃ ) δ: 1.23 (9H, s), 3.74 (2H, t), 4.55 (2H, t), 7.26 (1H, d), 8.12 ( 1H, s), 8.64 (1H, d), 9.18 (1H, s).
Compound 16
¹ H-NMR (CDCl ₃ ) δ: 1.23 (9H, s), 3.73 (2H, t), 4.55 (2H, t), 6.71 (1H, s), 7.21 ( 1H, s), 7.60 (1H, s), 8.41 (1H, s), 8.64 (1H, s).
Compound 17
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).
Compound 18
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).
Compound 19
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).
Compound 20
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).

Compound 21
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).
Compound 22
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).
Compound 23
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).
Compound 24
¹ H-NMR (CDCl ₃ ) δ: 1.27 (9H, s), 5.30 (2H, s), 6.81 (1H, d), 7.20-7.21 (1H, m), 7.59-7.60 (1H, m), 8.42 (1H, s), 8.55 (1H, d).
Compound 25
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).
Compound 26
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).
Compound 29
¹ H-NMR (CDCl ₃ ) δ: 1.17 (9H, s), 5.03 (1H, d), 7.39 (1H, d), 8.13 (1H, s), 8.55 ( 1H, s), 9.18 (1H, s), 9.73 (1H, d).
Compound 30
¹ H-NMR (CDCl ₃ ) δ: 1.28 (9H, s), 5.31 (2H, s), 7.36 (1H, d), 8.12 (1H, s), 8.54 ( 1H, d), 9.17 (1H, s).
Compound 31
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).
Compound 32
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).
Compound 33
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).
Compound 34
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).
Compound 35
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).
Compound 36
¹ H-NMR (CDCl ₃ ) δ: 3.45 (3H, s), 3.76-3.78 (2H, m), 4.60-4.63 (2H, m), 7.29 (1H , D), 8.11 (1H, s), 8.64 (1H, d), 9.18 (1H, s).
Compound 37
¹ H-NMR (CDCl ₃ ) δ: 3.45 (3H, s), 3.75-3.77 (2H, m), 4.60-4.62 (2H, m), 6.73 (1H , S), 7.20-7.21 (1H, m), 7.58-7.59 (1H, m), 8.40 (1H, s), 8.64 (1H, s).
Compound 38
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).
Compound 39
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).
Compound 40
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).

Compound 41
_{^{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).
Compound 42
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).
Compound 43
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).
Compound 44
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).
Compound 45
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).
Compound 46
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).
Compound 47
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).
Compound 48
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).
Compound 49
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).

Compound 51
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).
Compound 52
_{^{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).
Compound 53
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).
Compound 54
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) ).
Compound 55
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).
Compound 56
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).
Compound 57
¹ H-NMR (CDCl ₃ ) δ: 4.85-4.94 (2H, m), 5.98 (1H, tt), 7.32 (1H, d), 8.69 (1H, d), 9.07 (1H, s).
Compound 58
¹ H-NMR (CDCl ₃ ) δ: 4.87-4.95 (2H, m), 5.99 (1H, tt), 7.43 (1H, d), 8.74 (1H, d), 9.27 (1H, s).
Compound 59
¹ H-NMR (CDCl ₃ ) δ: 4.06 (3H, s), 4.85-4.95 (2H, m), 5.98 (1H, tt), 7.51-7.53 (1H , M), 8.72-8.74 (1H, m), 9.27 (1H, s).
Compound 60
¹ H-NMR (CDCl ₃ ) δ: 4.85-4.94 (2H, m), 5.98 (1H, tt), 7.30 (1H, d), 8.69 (1H, d), 9.10 (1H, s).

Compound 61
¹ H-NMR (CDCl ₃ ) δ: 2.50 (3H, s), 4.82-4.92 (2H, m), 5.85-6.12 (1H, m), 7.28 (1H , D), 8.65 (1H, d), 9.06 (1H, s).
Compound 62
¹ H-NMR (CDCl ₃ ) δ: 2.94 (3H, s), 4.84-4.92 (2H, m), 6.00 (1H, tt), 7.43 (1H, d), 7.93 (1H, s), 8.72 (1H, d).
Compound 63
¹ H-NMR (CDCl ₃ ) δ: 4.87-4.95 (2H, m), 5.84-6.13 (1H, m), 7.53 (1H, s), 8.74 (1H , S), 9.31 (1H, s).
Compound 64
¹ H-NMR (DMSO-D ₆ ) δ: 5.08 (2H, t), 6.60-6.86 (1H, m), 7.43 (1H, d), 7.85 (1H, brs) ), 8.12 (1H, brs), 8.92 (1H, d), 9.56 (1H, s).
Compound 65
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).
Compound 66
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).
Compound 67
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).
Compound 68
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).
Compound 69
¹ H-NMR (CDCl ₃ ) δ: 2.34 (6H, s), 2.75 (2H, t), 4.55 (2H, t), 7.27 (1H, d), 8.11 ( 1H, s), 8.64 (1H, d), 9.18 (1H, s).
Compound 70
¹ H-NMR (CDCl ₃ ) δ: 2.34 (6H, s), 2.73 (2H, t), 4.54 (2H, t), 6.72-6.74 (1H, m), 7.19-7.21 (1H, m), 7.57-7.59 (1H, m), 8.40 (1H, s), 8.64 (1H, s).
Compound 71
¹ H-NMR (DMSO-D ₆ ) δ: 5.02 (2H, t), 6.14 (2H, brs), 6.57-6.87 (1H, m), 6.94 (1H, s ), 8.74 (1H, s), 9.01 (1H, s).
Compound 72
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).
Compound 73
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).
Compound 74
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) ).
Compound 75
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).
Compound 76
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).
Compound 77
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).
Compound 78
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).
Compound 79
¹ H-NMR (CDCl ₃ ) δ: 5.22 (2H, s), 8.22 (1H, s), 8.63 (1H, s), 9.09 (1H, s).
Compound 80
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).

Compound 81
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).
Compound 82
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).
Compound 83
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).
Compound 84
¹ H-NMR (CDCl ₃ ) δ: 5.23 (2H, s), 8.24 (1H, s), 8.50 (1H, s), 9.12 (1H, s).
Compound 85
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).
Compound 86
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).
Compound 87
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).
Compound 88
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).
Compound 89
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).
Compound 90
¹ H-NMR (CDCl ₃ ) δ: 4.91-5.07 (3H, m), 8.17 (1H, s), 8.76 (1H, s), 9.22 (1H, s).
Compound 91
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).
Compound 92
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).
Compound 93
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).
Compound 94
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).
Compound 95
¹ H-NMR (CDCl ₃ ) δ: 1.20 (6H, d), 3.64-3.71 (1H, m), 3.79-3.81 (2H, m), 4.57-4 .60 (2H, m), 7.27 (1H, d), 8.11 (1H, s), 8.64 (1H, d), 9.18 (1H, s).
Compound 96
¹ H-NMR (CDCl ₃ ) δ: 0.91 (6H, d), 1.86-1.92 (1H, m), 3.29 (2H, d), 3.79-3.81 (2H , M), 4.59-4.62 (2H, m), 7.27 (1H, d), 8.12 (1H, s), 8.64 (1H, d), 9.18 (1H, s).
Compound 97
¹ H-NMR (CDCl ₃ ) δ: 1.18 (9H, s), 1.38 (3H, d), 3.47-3.50 (2H, m), 5.43-5.45 (1H M), 7.20 (1H, d), 8.11 (1H, s), 8.63 (1H, d), 9.17 (1H, s).
Compound 98
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).
Compound 99
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).
Compound 100
¹ H-NMR (CDCl ₃ ) δ: 4.81-4.94 (2H, m), 4.99-5.20 (1H, m), 7.36 (1H, d), 8.02 (1H , S), 8.81 (1H, d).

Compound 101
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).
Compound 102
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).
Compound 103
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).
Compound 104
¹ H-NMR (CDCl ₃ ) δ: 5.21 (2H, s), 8.22 (1H, s), 8.63 (1H, s), 9.05 (1H, s).
Compound 105
¹ H-NMR (CDCl ₃ ) δ: 1.22 (9H, s), 3.72 (2H, t), 4.52 (2H, t), 6.66 (2H, brs), 7.19 ( 1H, d), 7.58 (1H, s), 8.59 (1H, d).
Compound 106
¹ H-NMR (CDCl ₃ ) δ: 2.66 (3H, s), 4.77-4.88 (2H, m), 5.00-5.21 (1H, m), 7.16 (1H , S), 8.11 (1H, s), 9.19 (1H, s).
Compound 107
¹ H-NMR (CDCl ₃ ) δ: 2.66 (3H, s), 4.84-4.88 (2H, m), 6.00 (1H, tt), 7.15 (1H, s), 8.11 (1H, s), 9.19 (1H, s).
Compound 108
¹ H-NMR (CDCl ₃ ) δ: 2.66 (3H, s), 5.14 (2H, s), 7.23 (1H, s), 8.12 (1H, s), 9.20 ( 1H, s).
Compound 109
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).
Compound 110
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).
Compound 111
¹ H-NMR (CDCl ₃ ) δ: 2.25 (3H, s), 5.05 (2H, s), 7.37 (1H, s), 8.13 (1H, s), 8.59 ( 1H, s), 9.18 (1H, s).
Compound 112
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).
Compound 113
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).
Compound 114
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).
Compound 115
¹ H-NMR (CDCl ₃ ) δ: 1.70-1.78 (2H, m), 1.82-1.91 (3H, m), 3.25 (2H, t), 3.71-3 .77 (2H, m), 6.73 (2H, brs), 7.58 (1H, s), 7.66 (1H, d), 8.72 (1H, d).
Compound 116
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).
Compound 117
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).
Compound 118
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).
Compound 119
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).
Compound 120
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).

Compound 121
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).
Compound 122
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).
Compound 123
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).
Compound 124
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).
Compound 125
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).
Compound 126
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).
Compound 127
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).
Compound 128
¹ H-NMR (CDCl ₃ ) δ: 1.23 (9H, s), 3.79 (2H, t), 4.64 (2H, t), 8.20 (1H, s), 8.58 ( 1H, s), 9.03 (1H, s).
Compound 129
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).
Compound 130
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).
Compound 131
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).
Compound 132
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).
Compound 133
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).
Compound 134
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).
Compound 135
¹ H-NMR (CDCl ₃ ) δ: 1.24 (9H, s), 2.47 (3H, s), 3.76 (2H, t), 4.56 (2H, t), 8.13 ( 1H, s), 8.52 (1H, s), 9.04 (1H, s).
Compound 136
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).
Compound 137
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).
Compound 138
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).
Compound 139
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).
Compound 140
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).

Compound 141
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).
Compound 142
¹ H-NMR (CDCl ₃ ) δ: 2.66-2.82 (2H, m), 4.86 (2H, t), 8.21 (1H, s), 8.62 (1H, s), 9.06 (1H, s).
Compound 143
¹ H-NMR (CDCl ₃ ) δ: 2.48 (3H, s), 2.62-2.77 (2H, m), 4.79 (2H, t), 8.14 (1H, s), 8.55 (1H, s), 9.07 (1H, s).
Compound 144
¹ H-NMR (CDCl ₃ ) δ: 2.60-2.75 (2H, m), 4.78 (2H, t), 7.26 (1H, s), 8.12 (1H, s), 8.67 (1H, s), 9.19 (1H, s).
Compound 145
¹ H-NMR (CDCl ₃ ) δ: 5.08 (2H, t), 8.22 (1H, s), 8.63 (1H, s), 9.09 (1H, s).
Compound 146
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).
Compound 147
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).
Compound 148
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).
Compound 149
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).
Compound 150
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).
Compound 151
¹ H-NMR (DMSO-D ₆ ) δ: 3.94 (2H, t), 5.11 (2H, t), 6.03 (1H, brs), 7.35 (1H, s), 8. 42 (1H, s), 8.89 (1H, s), 9.49 (1H, s).
Compound 152
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).
Compound 153
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).
Compound 154
¹ H-NMR (CDCl ₃ ) δ: 3.51 (3H, s), 3.88 (2H, t), 4.98 (2H, t), 7.37 (1H, s), 8.13 ( 1H, s), 8.68 (1H, s), 9.19 (1H, s).
Compound 155
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).
Compound 156
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).
Compound 157
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).
Compound 158
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).
Compound 159
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).
Compound 160
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).

Compound 161
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).
Compound 162
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).
Compound 163
¹ H-NMR (CDCl ₃ ) δ: 4.45-4.64 (1H, m), 4.70-4.92 (2H, m), 7.17-7.20 (1H, m), 7 .34-7.35 (1H, m), 7.40-7.42 (1H, m), 7.49-7.51 (1H, m), 7.84 (1H, s), 8.78 (1H, s), 8.99 (1H, s).
Compound 164
¹ H-NMR (CDCl ₃ ) δ: 4.78-4.87 (2H, m), 5.59 (1H, tt), 7.18-7.20 (1H, m), 7.34 (1H , Td), 7.40 (1H, td), 7.47-7.49 (1H, m), 7.83 (1H, s), 8.78 (1H, s), 8.95 (1H, s).
Compound 165
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).
Compound 166
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).
Compound 167
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).
Compound 168
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).
Compound 169
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).
Compound 170
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).
Compound 171
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).
Compound 172
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).
Compound 173
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).
Compound 174
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).
Compound 175
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).
Compound 176
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).
Compound 177
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).
Compound 178
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).
Compound 179
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).
Compound 180
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).

Compound 181
¹ H-NMR (CDCl ₃ ) δ: 1.55 (1.5 H, d), 1.58 (1.5 H, d), 4.26-4.62 (1.0 H, m), 5.49 -5.60 (0.5H, m), 5.61-5.71 (0.5H, m), 7.15-7.16 (2.0H, m), 7.42-7.44 ( 3.0H, m), 7.88-7.89 (1.0H, m), 8.59-8.61 (1.0H, m), 8.75-8.76 (1.0H, m ).
Compound 182
¹ H-NMR (CDCl ₃ ) δ: 1.29 (3H, s), 4.70 (2H, s), 7.14-7.16 (2H, m), 7.39-7.41 (3H M), 7.91 (1H, s), 8.49 (1H, s), 8.76 (1H, s).
Compound 183
¹ H-NMR (CDCl ₃ ) δ: 5.16 (2H, s), 7.24-7.27 (2H, m), 7.41-7.41 (3H, m), 7.93 (1H , S), 8.48 (1H, s), 8.77 (1H, s).
Compound 184
¹ H-NMR (CDCl ₃ ) δ: 1.98-2.08 (4H, m), 4.49 (2H, t), 7.16-7.16 (2H, m), 7.40-7 .41 (3H, m), 7.90 (1H, s), 8.43 (1H, s), 8.74 (1H, s).
Compound 185
¹ H-NMR (CDCl ₃ ) δ: 0.87-0.97 (3H, m), 1.30-1.41 (2H, m), 1.43-1.54 (2H, m), 2 .28-2.40 (2H, m), 5.08-5.17 (2H, m), 7.25 (1H, s), 8.13 (1H, s), 8.65-8.68 (1H, m), 9.19 (1H, s).
Compound 186
¹ H-NMR (CDCl ₃ ) δ: 0.86-0.97 (3H, m), 1.24-1.89 (6H, m), 2.28-2.44 (1H, m), 4 .38-5.02 (3H, m), 7.26 (1H, s), 8.13 (1H, s), 8.64-8.68 (1H, m), 9.17-9.20 (1H, m).
Compound 187
¹ H-NMR (CDCl ₃ ) δ: 3.97-4.14 (4H, m), 4.85-5.03 (2H, m), 5.93 (1H, tt), 7.37 (1H , S), 8.13 (1H, s), 8.68 (1H, s), 9.20 (1H, s).
Compound 188
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).
Compound 189
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).
Compound 190
¹ H-NMR (CDCl ₃ ) δ: 4.73-4.76 (2H, m), 5.00-5.18 (3H, m), 6.71 (1H, s), 8.08 (1H , S), 9.07 (1H, s).
Compound 191
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).
Compound 192
¹ H-NMR (CDCl ₃ ) δ: 3.64-3.77 (1H, m), 3.92-4.10 (1H, m), 5.16-5.33 (1H, m), 8 21-8.21 (1H, m), 8.60-8.62 (1H, m), 9.11 (1H, s), 9.30 (1H, s).
Compound 193
¹ H-NMR (CDCl ₃ ) δ: 4.26-4.39 (1H, m), 4.46-4.53 (1H, m), 5.21-5.37 (1H, m), 8 .24 (1H, s), 8.54 (1H, d), 9.25 (1H, d), 9.32 (1H, s).
Compound 194
¹ H-NMR (CDCl ₃ ) δ: 2.23 (3H, s), 4.82-4.85 (1H, m), 4.97-5.07 (1H, m), 5.39-5 .54 (1H, m), 8.21 (1H, s), 8.53 (1H, s), 9.06 (1H, s), 9.20 (1H, s).
Compound 195
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).
Compound 196
¹ H-NMR (CDCl ₃ ) δ: 0.11 (9H, s), 1.17 to 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).
Compound 1973
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).
Compound 198
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).
Compound 199
¹ H-NMR (CDCl ₃ ) δ: 1.89-2.01 (1H, m), 2.24 (3H, s), 2.38-2.50 (1H, m), 3.17-3 .30 (1H, m), 4.62-4.74 (2H, m), 7.25 (1H, s), 8.12 (1H, s), 8.67 (1H, s), 9. 19 (1H, s).
Compound 200
¹ H-NMR (CDCl ₃ ) δ: 1.93-2.05 (1H, m), 2.24 (3H, s), 2.42-2.52 (4H, m), 3.14-3 .28 (1H, m), 4.63-4.76 (2H, m), 8.14 (1H, s), 8.54 (1H, s), 9.07 (1H, s).

Compound 201
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).
Compound 202
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).
Compound 203
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).
Compound 204
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).
Compound 205
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).
Compound 206
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).
Compound 207
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).
Compound 208
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).
Compound 209
¹ H-NMR (CDCl ₃ ) δ: 2.23 (3H, s), 2.48 (3H, s), 2.93 (2H, t), 4.65 (2H, t), 8.13 ( 1H, s), 8.52 (1H, s), 9.05 (1H, s).
Compound 210
_{^{1 H-NMR (CDCl 3)}} δ: 1.21 (6H, s), 2.38 (6H, s), 2.50 (3H, s), 4.38 (2H, s), 8.13 ( 1H, s), 8.53 (1H, s), 9.05 (1H, s).
Compound 211
¹ H-NMR (CDCl ₃ ) δ: 1.19 (9H, s), 1.39 (3H, d), 2.44 (3H, d), 3.47 (1H, dd), 3.62 ( 1H, dd), 5.39-5.49 (1H, m), 8.13 (1H, s), 8.51 (1H, s), 9.02 (1H, s).
Compound 212
¹ H-NMR (CDCl ₃ ) δ: 1.39 (3H, d), 2.45 (3H, s), 3.41 (3H, s), 3.56 (1H, dd), 3.65 ( 1H, dd), 5.53-5.62 (1H, m), 8.13 (1H, s), 8.52 (1H, s), 9.03 (1H, s).
Compound 213
¹ H-NMR (CDCl ₃ ) δ: 2.54 (3H, s), 4.83-4.93 (2H, m), 4.96-5.18 (1H, m), 8.55 (1H , S), 9.05 (1H, s).
Compound 214
¹ H-NMR (CDCl ₃ ) δ: 2.13 (3H, s), 4.80-5.14 (3H, m), 7.57 (1H, s), 8.66 (1H, s).
Compound 215
¹ H-NMR (CDCl ₃ ) δ: 2.57 (3H, s), 4.05 (3H, s), 4.83-4.95 (2H, m), 4.96-5.18 (1H M), 8.59 (1H, s), 9.16 (1H, s).
Compound 216
¹ H-NMR (CDCl ₃ ) δ: 2.53 (3H, s), 4.80-4.93 (2H, m), 4.96-5.18 (1H, m), 8.55 (1H , S), 9.01 (1H, s).
Compound 217
¹ H-NMR (CDCl ₃ ) δ: 2.55 (3H, s), 4.82-4.95 (2H, m), 4.97-5.18 (1H, m), 8.59 (1H , S), 9.19 (1H, s).
Compound 218
¹ H-NMR (CDCl ₃ ) δ: 2.11 (3H, s), 4.82-4.96 (2H, m), 4.97-5.17 (1H, m), 7.14 (2H , S), 8.68 (1H, s).
Compound 219
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).
Compound 220
_{^{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).

Compound 221
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).
Compound 222
¹ H-NMR (CDCl ₃ ) δ: 2.69 (3H, s), 8.16 (1H, s), 8.76 (1H, s), 9.16 (1H, s).
Compound 223
¹ H-NMR (CDCl ₃ ) δ: 2.09-2.19 (5H, m), 2.47 (3H, s), 2.69 (2H, t), 4.57 (2H, t), 8.13 (1H, s), 8.52 (1H, s), 9.05 (1H, s).
Compound 224
¹ H-NMR (CDCl ₃ ) δ: 1.31 (3H, t), 2.48 (3H, s), 2.67 (2H, q), 2.95 (2H, t), 4.63 ( 2H, t), 8.13 (1H, s), 8.52 (1H, s), 9.05 (1H, s).
Compound 225
¹ H-NMR (CDCl ₃ ) δ: 1.75-1.85 (2H, m), 1.91-2.01 (2H, m), 2.12 (3H, s), 2.46 (3H , S), 2.59 (2H, t), 4.48 (2H, t), 8.13 (1H, s), 8.52 (1H, s), 9.04 (1H, s).
Compound 226
¹ H-NMR (CDCl ₃ ) δ: 2.51 (3H, s), 4.33-4.55 (2H, m), 4.65-4.79 (1H, m), 4.94-5 .10 (1H, m), 8.12 (1H, s), 8.55 (1H, s), 9.08 (1H, s).
Compound 227
¹ H-NMR (CDCl ₃ ) δ: 2.54 (3H, s), 3.70 (3H, s), 3.95-4.05 (1H, m), 4.75-4.93 (2H M), 8.15 (1H, s), 8.56 (1H, s), 9.10 (1H, s).
Compound 228
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).
Compound 229
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).
Compound 230
¹ H-NMR (CDCl ₃ ) δ: 1.27 (3H, t), 1.68 (4H, dd), 2.54 (3H, s), 4.23 (2H, q), 5.42 ( 1H, q), 8.13 (1H, s), 8.47 (1H, s), 9.05 (1H, s).
Compound 231
¹ H-NMR (CDCl ₃ ) δ: 1.70 (3H, d), 2.55 (3H, s), 3.77 (3H, s), 5.46 (1H, q), 8.14 ( 1H, s), 8.48 (1H, s), 9.06 (1H, s).
Compound 232
¹ H-NMR (CDCl ₃ ) δ: 1.12 (3H, t), 2.02-2.12 (2H, m), 2.55 (3H, s), 3.76 (3H, s), 5.30 (1H, t), 8.14 (1H, s), 8.47 (1H, s), 9.05 (1H, s).
Compound 233
¹ H-NMR (CDCl ₃ ) δ: 1.01 (3H, t), 1.27 (3H, t), 1.51-1.64 (2H, m), 1.91-2.11 (2H M), 2.54 (3H, s), 4.22 (2H, q), 5.32 (1H, dd), 8.14 (1H, s), 8.46 (1H, s), 9 .05 (1H, s).
Compound 234
¹ H-NMR (CDCl ₃ ) δ: 1.18 (3H, t), 1.74 (6H, s), 2.49 (3H, s), 4.18 (2H, q), 8.13 ( 1H, s), 8.43 (1H, s), 9.03 (1H, s).
Compound 235
¹ H-NMR (CDCl ₃ ) δ: 1.15 (3H, t), 2.53-2.58 (5H, m), 5.07 (2H, s), 8.14 (1H, s), 8.45 (1H, s), 9.06 (1H, s).
Compound 236
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).
Compound 237
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).
Compound 238
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).
Compound 239
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).
Compound 240
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).

Compound 241
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).
Compound 242
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).
Compound 243
¹ H-NMR (CDCl ₃ ) δ: 2.51 (3H, s), 3.06 (3H, s), 3.55 (2H, t), 4.96 (2H, t), 8.14 ( 1H, s), 8.56 (1H, s), 9.09 (1H, s).
Compound 244
¹ H-NMR (CDCl ₃ ) δ: 2.42 (2H, dd), 2.48 (3H, s), 2.98 (3H, s), 3.23 (2H, dd), 4.62 ( 2H, t), 8.14 (1H, s), 8.53 (1H, s), 9.07 (1H, s).
Compound 245
¹ H-NMR (CDCl ₃ ) δ: 1.98-2.15 (4H, m), 2.47 (3H, s), 2.94 (3H, s), 3.13 (2H, dd), 4.51 (2H, t), 8.13 (1H, s), 8.52 (1H, s), 9.05 (1H, s).
Compound 246
¹ H-NMR (CDCl ₃ ) δ: 2.49 (3H, s), 2.71 (3H, s), 3.09-3.18 (1H, m), 3.20-3.30 (1H M), 4.86-5.01 (2H, m), 8.14 (1H, s), 8.54 (1H, s), 9.07 (1H, s).
Compound 247
¹ H-NMR (CDCl ₃ ) δ: 1.26 (2H, t), 1.96-2.04 (2H, m), 2.47 (3H, s), 2.60 (3H, s), 2.69-2.88 (2H, m), 4.46-4.56 (2H, m), 8.13 (1H, s), 8.52 (1H, s), 9.05 (1H, s).
Compound 248
¹ H-NMR (CDCl ₃ ) δ: 2.48 (3H, s), 3.34 (2H, t), 4.72 (2H, t), 8.13 (1H, s), 8.53 ( 1H, s), 9.07 (1H, s).
Compound 249
¹ H-NMR (CDCl ₃ ) δ: 1.23-1.30 (3H, m), 2.54 (3H, s), 3.73-3.86 (1H, m), 3.91-4 .01 (1H, m), 4.04-4.16 (1H, m), 4.74-4.95 (2H, m), 8.15 (1H, s), 8.56 (1H, s ), 9.10 (1H, s).
Compound 250
¹ H-NMR (CDCl ₃ ) δ: 1.27 (3H, t), 2.13-2.22 (2H, m), 2.46 (3H, s), 2.51 (2H, t), 4.16 (2H, q), 4.50 (2H, t), 8.13 (1H, s), 8.51 (1H, s), 9.04 (1H, s).
Compound 251
¹ H-NMR (CDCl ₃ ) δ: 1.59 (3H, d), 2.24 (3H, s), 2.55 (3H, s), 5.44 (1H, q), 8.14 ( 1H, s), 8.45 (1H, s), 9.06 (1H, s).

Next, formulation examples are shown. In addition, a part represents a weight part.

Formulation Example 1
10 parts of each of compounds 1 to 251 are dissolved in a mixture of 35 parts of xylene and 35 parts of N, N-dimethylformamide, 14 parts of polyoxyethylene styrylphenyl ether and 6 parts of calcium dodecylbenzenesulfonate are added and stirred well. Mix to obtain each 10% emulsion.

Formulation Example 2
20 parts of each of compounds 1 to 251 were added to 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, and mixed well with stirring. Obtain a% wettable powder.

Formulation Example 3
To 2 parts of each of compounds 1 to 251 are added 1 part of a synthetic silicon hydrous fine powder, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65 parts of kaolin clay and mixed 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
Dissolve 1 part of each of compounds 1 to 251 in an appropriate amount of acetone, add 5 parts of synthetic silicon hydroxide fine powder, 0.3 part of PAP and 93.7 parts of fusami clay, and mix well with stirring to evaporate and remove acetone. Each 1% powder is obtained.

Formulation Example 5
10 parts of each of compounds 1 to 251, 35 parts of white carbon containing 50 parts of polyoxyethylene alkyl ether sulfate ammonium salt and 55 parts of water are mixed and finely pulverized by a wet pulverization method to obtain each 10% flowable agent. obtain.

Formulation Example 6
0.1 part of each of compounds 1 to 251 is 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
10 mg of each of compounds 1 to 251 is dissolved in 0.5 ml of acetone, and this solution is processed into 5 g of animal solid feed powder (bred breeding solid feed powder CE-2, Nippon Claire Co., Ltd.) and mixed uniformly. To do. Then, acetone is evaporated to dryness to obtain each poisonous bait.

  Next, the pest control effect of the compound of the present invention is shown by test examples.

Test example 1
Compounds 8, 11, 15, 18, 21, 22, 25, 26, 33-35, 37, 39, 44, 45, 47-49, 51, 52, 55, 60, 61, obtained by Formulation Example 5 65-68, 73-75, 77, 79, 82-89, 91-94, 96, 102, 106, 107, 109, 110, 112, 114, 116, 117, 119, 120, 122, 123, 131- 134,140,141,146,148-150,152,156,180,188,189,190,195,196,199-202,204,205,208,220,221,227-229,236-238, The preparations 240 and 241 were diluted with water so that the active ingredient concentration was 500 ppm to prepare test chemicals.
About 30 aphids (Aphis gossypii) were inoculated on the cucumber seedlings in the second true leaf development stage planted in a polyethylene cup, and 10 ml of the test chemical solution was sprayed one day after the inoculation.
Five days after spraying, the number of live cotton aphids that parasitized on the leaves of the cucumber was examined, and the control value was determined by the following formula.
Control value (%) = {1− (Cb × Tai) / (Cai × Tb)} × 100
In addition, the character in a formula represents the following meaning.
Cb: number of insects before treatment in the untreated group Cai: number of insects when observed in the untreated group Tb: number of insects before treatment in the treated group Tai: number of insects when observed in the treated group As a result, compounds 8, 11 15, 18, 21, 22, 25, 26, 33-35, 37, 39, 44, 45, 47-49, 51, 52, 55, 60, 61, 65-68, 73-75, 77, 79, 82-89, 91-94, 96, 102, 106, 107, 109, 110, 112, 114, 116, 117, 119, 120, 122, 123, 131-134, 140, 141, 146, 148-150, Of 152, 156, 180, 188, 189, 190, 195, 196, 199-202, 204, 205, 208, 220, 221, 227-229, 236-238, 240 and 241 The treated area showed a control value of 90% or more.

Test example 2
Compound 3, 6-11, 14-16, 19-23, 25, 26, 33-35, 44-49, 52, 53, 55, 60, 65, 66, 71-73, obtained by Formulation Example 5 75, 77-80, 82-89, 91-95, 100-104, 107-110, 112-114, 116-128, 131-141, 143, 145, 148-150, 152, 155, 159, 162, 167, 169, 172, 176, 178-180, 188, 189, 194, 196, 199-209, 211, 219-221, 223-225, 227-229, 236-238 and 240-242 and active ingredients It diluted with water so that a density | concentration might be 500 ppm, and prepared the chemical | medical solution for a test.
Tomato seedlings in the third true leaf development stage planted in polyethylene cups were released adult adult whiteflies (Bemisia tabaci) and allowed to lay eggs for about 24 hours. The tomato seedlings were kept in a greenhouse for 8 days, and the test chemical solution was sprayed at a rate of 10 ml / cup to the place where the larvae had hatched from the delivered eggs. The cup was kept in a greenhouse at 25 ° C. Seven days later, the number of surviving larvae on the tomato leaves was examined, and the control value was determined by the following formula.
Control value (%) = {1− (Cb × Tai) / (Cai × Tb)} × 100
In addition, the character in a formula represents the following meaning.
Cb: number of insects before treatment in the untreated group Cai: number of insects at the time of observation of the untreated group Tb: number of insects before treatment of the treated group Tai: number of insects at the time of observation of the treated group

As a result, compounds 3, 6-11, 14-16, 19-23, 25, 26, 33-35, 44-49, 52, 53, 55, 60, 65, 66, 71-73, 75, 77- 80, 82-89, 91-95, 100-104, 107-110, 112-114, 116-128, 131-141, 143, 145, 148-150, 152, 155, 159, 162, 167, 169, 172, 176, 178-180, 188, 189, 194, 196, 199-209, 211, 219-221, 223-225, 227-229, 236-238 and 240-242 test spray treatment zones are The control value was 90% or more.

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

Claims (28)

Formula (1)

[Where,
Q represents oxygen or -S (O) n-
n represents 0, 1 or 2;
G ¹ represents nitrogen or CR ⁶
R ¹ , R ² and R ⁶ are the same or different and are hydrogen, halogen, nitro group, cyano group, C1-C6 chain hydrocarbon group optionally substituted with halogen, -L ¹ R ⁷ , -C ( = O) R ⁸ , to a phenyl group optionally substituted with one or more groups selected from group A or to a 5-membered or 6-membered aromatic optionally substituted with one or more groups selected from group A Represents a terrorist ring group,
L ¹ represents oxygen, —S (O) n— or —NR ⁹ —,
R ⁷ represents a C1-C6 chain hydrocarbon group which may be substituted with hydrogen or halogen (provided that when L ¹ is —S (O) n— and n is 1 or 2, ⁷ is not hydrogen)
R ⁸ is hydrogen, a hydroxy group, an amino group, a C1-C6 chain hydrocarbon group which may be substituted with halogen, a C1-C6 alkoxy group which may be substituted with halogen, or a halogen. A C1-C4 alkylamino group or a C2-C8 dialkylamino group optionally substituted with halogen,
R ⁹ represents hydrogen, a C1-C6 chain hydrocarbon group which may be substituted with halogen, or a C1-C6 alkylsulfonyl group which may be substituted with halogen,
R ³ represents hydrogen, halogen, a C1-C6 chain hydrocarbon group which may be substituted with halogen, a C3-C8 cycloalkyl group which may be substituted with halogen, or -L ² R ¹⁰ ;
R ⁴ is hydrogen, halogen, nitro group, cyano group, C1-C6 chain hydrocarbon group optionally substituted with halogen, C3-C8 cycloalkyl group optionally substituted with halogen, -L ² R ¹⁰ , -C (= O) R ¹¹ , a phenyl group optionally substituted with one or more groups selected from group A, or 5- or optionally substituted with one or more groups selected from group A Represents a 6-membered aromatic heterocyclic group,
L ² represents oxygen, —S (O) n— or —NR ¹² —,
When R ¹⁰ represents a hydrogen or halogen substituted C6 C1-may be a chain hydrocarbon group (provided, L ² is -S (O) is n-, n is 1 or 2, R ¹⁰ is not hydrogen)
R ¹¹ is hydrogen, a hydroxy group, an amino group, a C1-C6 chain hydrocarbon group optionally substituted with halogen, a C1-C6 alkoxy group optionally substituted with halogen, or optionally substituted with halogen. A C1-C4 alkylamino group or a C2-C8 dialkylamino group optionally substituted with halogen,
R ¹² represents hydrogen, a C1-C6 chain hydrocarbon group which may be substituted with halogen, or a C1-C6 alkylsulfonyl group which may be substituted with halogen;
R ⁵ represents a C1-C10 alkyl group substituted with one or more groups selected from Group B or a C3-C10 alkenyl group substituted with one or more groups selected from Group B;
Group A includes halogen, amino group, cyano group, nitro group, C1-C6 chain hydrocarbon group optionally substituted with halogen, C1-C6 alkoxy group optionally substituted with halogen, and S (O) nR. ¹³ wherein R ¹³ represents a C1-C6 alkyl group optionally substituted with halogen,
Group B is halogen, -L ³ R ^14, and -C (= O) R ^15,
{L ³ represents oxygen, —S (O) n—, —NR ¹⁶ — or —Si (R ¹⁷ ) ₂ —,
R ¹⁴ represents hydrogen or a C1-C6 chain hydrocarbon group which may be substituted with halogen (where L ³ is —S (O) n— and n is 1 or 2). , R ¹⁴ is not hydrogen)
R ¹⁵ is hydrogen, a C1-C6 chain hydrocarbon group which may be substituted with halogen, a C1-C4 alkylamino group which may be substituted with halogen, or a C2-C8 dialkylamino group which may be substituted with halogen. A C1-C6 alkoxy group optionally substituted with a group or halogen,
R ¹⁶ represents a hydrogen or halogen substituted C6 C1-may be a chain hydrocarbon group,
R ¹⁷ 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. ]
The pyrimidine compound shown by these. R ¹ , R ² and R ⁶ are the same or different and are hydrogen, halogen, nitro group, cyano group, C1-C6 chain hydrocarbon group optionally substituted with halogen, -L ¹ R ⁷ or -C ( = O) a R ⁸ is claim 1 pyrimidine compound according. R ¹ , R ² and R ⁶ are the same or different and are hydrogen, halogen, a C1-C6 chain hydrocarbon group optionally substituted with halogen, -L ¹ R ⁷ , or -C (= O) R ⁸ The pyrimidine compound according to claim 1 or 2. R ¹ and R ⁶ are the same or different and are hydrogen, halogen, a C1-C6 chain hydrocarbon group optionally substituted with halogen, or -C (= O) R ⁸ . The pyrimidine compound according to one item. The pyrimidine compound according to any one of claims 1 to 4, wherein R ² is hydrogen, halogen, a C1-C6 chain hydrocarbon group which may be substituted with halogen, or -L ¹ R ⁷ . 2. R ⁴ is hydrogen, halogen, a C1-C6 chain hydrocarbon group which may be substituted with halogen, a C3-C8 cycloalkyl group which may be substituted with halogen, or —L ² R ^10. The pyrimidine compound as described in any one of -5. R ³ is hydrogen, halogen, a C1-C6 chain hydrocarbon group which may be substituted with halogen, or a C3-C8 cycloalkyl group which may be substituted with halogen. The pyrimidine compound described. R ³ is preceding claims any one pyrimidine compound according hydrogen. Q is oxygen, The pyrimidine compound as described in any one of Claims 1-8. R ⁵ is halogen or -L ³ R ¹⁴ C1-C10 alkyl or C3-C10 alkenyl claims 1-9 any one pyrimidine compound according substituted with. The pyrimidine compound according to any one of claims 1 to 10, wherein R ⁵ is a C1-C10 alkyl or C3-C10 alkenyl group substituted with a halogen. Q is oxygen, G ¹ is nitrogen or CR ⁶ , R ¹ and R ⁶ are the same or different, and are hydrogen, halogen, or a C1-C6 chain hydrocarbon group optionally substituted with halogen , R ² is hydrogen, halogen, a C1-C6 chain hydrocarbon group optionally substituted with halogen, or -L ¹ R ⁷ , and R ³ is hydrogen or halogen optionally substituted C1- A C6-chain hydrocarbon group, R ⁴ is hydrogen, halogen, or a C1-C6 chain hydrocarbon group optionally substituted with halogen, and R ⁵ is substituted with halogen or —L ³ R ¹⁴ The pyrimidine compound according to claim 1, which is a C1-C10 alkyl or C3-C10 alkenyl group. A pest control agent comprising the pyrimidine compound according to any one of claims 1 to 12 and an inert carrier. Use of the pyrimidine compound according to any one of claims 1 to 12 for controlling pests. A pest control method comprising a step of applying an effective amount of the pyrimidine compound according to any one of claims 1 to 12 to a pest or a pest habitat. 4- (2,2,3,3-tetrafluoropropoxy) -6-([1,2,4] triazol-1-yl) -pyrimidine 5-Methyl-4- (2,2,3,3-tetrafluoropropoxy) -6-([1,2,4] triazol-1-yl) -pyrimidine 5-Chloro-4- (2,2,3,3-tetrafluoropropoxy) -6-([1,2,4] triazol-1-yl) -pyrimidine 4- (2,2,3,4,4,4-Hexafluorobutyoxy) -6-([1,2,4] triazol-1-yl) -pyrimidine 4- (2,2,3,4,4,4-Hexafluorobutyoxy) -5-methyl-6-([1,2,4] triazol-1-yl) -pyrimidine 5-chloro-4- (2,2,3,4,4,4-hexafluorobutyroxy) -6-([1,2,4] triazol-1-yl) -pyrimidine 4- (2,2,3,3,4,4,5,5-octafluoropentyloxy) -5-methyl-6-[[1,2,4] triazol-1-yl) -pyrimidine 5-Chloro-4- (2,2,3,3,4,4,5,5-octafluoropentyloxy) -6-[[1,2,4] triazol-1-yl) -pyrimidine 4- (2-Chloro-2-methylpropoxy) -5-methyl-6-[[1,2,4] triazol-1-yl) -pyrimidine 4- (2,2-dichloropropoxy) -5-methyl-6-([1,2,4] triazol-1-yl) -pyrimidine Formula (4)

[Wherein C ′ is oxygen, R ³ is hydrogen, R ⁴ is hydrogen, halogen or a C1-C6 chain hydrocarbon group, and R ⁵ is substituted with one or more halogens. A C10 alkyl group or a C3-C10 alkenyl group substituted with one or more halogens. ]
The pyrimidine compound shown by these. Formula (2)

[Wherein, G ¹ represents nitrogen or CR ⁶ , R ⁶ represents hydrogen, R ¹ represents hydrogen or halogen, R ² represents hydrogen, halogen or an amino group, R ³ represents hydrogen, ⁴ represents a halogen, a nitro group, a cyano group or a halogen-substituted C6 C1-may be a chain hydrocarbon group. ]
The pyrimidine compound shown by these. Formula (6)

[Wherein, G ¹ represents nitrogen or CR ⁶ , R ⁶ represents hydrogen, R ¹ represents hydrogen or halogen, R ² represents hydrogen, halogen or an amino group, R ³ represents hydrogen, ⁴ represents a halogen, a nitro group, a cyano group or a halogen-substituted C6 C1-may be a chain hydrocarbon group. ]
The pyrimidine compound shown by these.