JP2018070512A - Harmful arthropod control composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a composition having excellent control effect on harmful arthropods.SOLUTION: The present invention provides a composition that shows excellent control effect on harmful arthropods and contains a compound represented by formula (I) or a salt thereof and an inert support. [Ris a C1-C8 chain hydrocarbon group, a C3-C7 cycloalkyl group, a phenyl group, a 5-10 membered heteroaryl group or a 3-7 membered saturated heterocycle group or the like; Gis CH, C(CH) or C(CN); Gis a single bond or CRR; Gis a single bond or CRR; Gis a single bond or CRR; Gis a single bond or CRR; Gis a single bond or CRR; Gis CRR; R-Rindependently represent halogen, nitro, cyano, alkyne, aryl or the like; and X is H or a C1-C3 alkoxy group and the like].SELECTED DRAWING: None

Description

  The present invention relates to a harmful arthropod control composition.

で示される化合物が記載されている。また、医薬用途としてある種の化合物が知られている（例えば特許文献２参照）。 In Patent Document 1, there is a formula (X).

Are described. In addition, certain compounds are known for pharmaceutical use (see, for example, Patent Document 2).

International Publication No. 2014/119696 International Publication No. 2016/040515

  An object of the present invention is to provide a harmful arthropod control composition having an excellent control effect.

As a result of studies to find a harmful arthropod composition having excellent control efficacy, the present inventors have found that a composition containing a compound represented by the following formula (I) and an inert carrier is a harmful arthropod. Has been found to have an excellent control effect against the above, and the present invention has been reached.
That is, the present invention is as follows.

〔式中、
Ｒ¹は、群Ａ１より選ばれる１以上の置換基を有してもよいＣ１−Ｃ８鎖式炭化水素基、群Ａ２より選ばれる１以上の置換基を有してもよいＣ３−Ｃ７シクロアルキル基、群Ａ２より選ばれる１以上の置換基を有してもよいフェニル基、群Ａ２より選ばれる１以上の置換基を有してもよい５−１０員ヘテロアリール基、又は群Ｂより選ばれる１以上の置換基を有してもよい３−７員飽和へテロ環基を表し、
Ｇ¹は、ＣＨ、Ｃ（ＣＨ₃）、又はＣ（ＣＮ）を表し、
Ｇ²は、ＣＲ²Ｒ³を表し、
Ｇ³は、単結合又はＣＲ⁴Ｒ⁵を表し、
Ｇ⁴は、単結合又はＣＲ⁶Ｒ⁷を表し、
Ｇ⁵は、単結合又はＣＲ⁸Ｒ⁹を表し、
Ｇ⁶は、単結合又はＣＲ¹⁰Ｒ¹¹を表し、
Ｇ⁷は、ＣＲ¹²Ｒ¹³を表し、
Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ｒ⁶、Ｒ⁷、Ｒ⁸、Ｒ⁹、Ｒ¹⁰、Ｒ¹¹、Ｒ¹²、及びＲ¹³は、各々独立して、ハロゲン原子、ニトロ基、シアノ基、ホルミル基、ＮＲ¹⁸Ｒ¹⁹｛Ｒ¹⁸及びＲ¹⁹は、各々独立して、１以上のハロゲン原子を有してもよいＣ１−Ｃ６アルキル基又は水素原子を表す｝、群Ｃより選ばれる１以上の置換基を有してもよいＣ１−Ｃ８鎖式炭化水素基、１以上のハロゲン原子を有してもよいＣ１−Ｃ４アルコキシ基、群Ｄより選ばれる１以上の置換基を有してもよいＣ６−Ｃ１０アリール基、群Ｄより選ばれる１以上の置換基を有してもよいＣ６−Ｃ１０アリールオキシ基、群Ｄより選ばれる１以上の置換基を有してもよい５−１０員ヘテロアリール基、群Ｄより選ばれる１以上の置換基を有してもよいＣ３−Ｃ７シクロアルキル基又は水素原子を表し、
Ｘは水素原子、ハロゲン原子、Ｃ１−Ｃ３鎖式炭化水素基、シアノ基、ホルミル基、ヒドロキシ基、又はＣ１−Ｃ３アルコキシ基を表す。
群Ａ１：群Ａ２より選ばれる１以上の置換基を有してもよいＣ３−Ｃ７シクロアルキル基、群Ａ２より選ばれる１以上の置換基を有してもよいフェニル基、群Ａ２より選ばれる１以上の置換基を有してもよい５−１０員ヘテロアリール基、群Ｂより１以上の置換基を有してもよい３−７員飽和へテロ環基、ハロゲン原子、１以上のハロゲン原子を有してもよいＣ１−Ｃ４アルコキシ基、ヒドロキシ基、１以上のハロゲン原子を有してもよいＣ２−Ｃ５アルコキシカルボニル基、ＮＲ¹⁴Ｒ¹⁵及びＣ（Ｏ）ＮＲ¹⁴Ｒ¹⁵からなる群｛Ｒ¹⁴及びＲ¹⁵は、各々独立して、１以上のハロゲン原子を有してもよいＣ１−Ｃ６アルキル基又は水素原子を表す｝。
群Ａ２：ハロゲン原子、１以上のハロゲン原子を有してもよいＣ１−Ｃ４アルキル基、１以上のハロゲン原子を有してもよいＣ１−Ｃ４アルコキシ基、ヒドロキシ基、ニトロ基、シアノ基、ホルミル基、１以上のハロゲン原子を有してもよいＣ２−Ｃ５アルコキシカルボニル基、ＮＲ¹⁶Ｒ¹⁷及びＣ（Ｏ）ＮＲ¹⁶Ｒ¹⁷からなる群｛Ｒ¹⁶及びＲ¹⁷は、各々独立して、１以上のハロゲン原子を有してもよいＣ１−Ｃ６アルキル基又は水素原子を表す｝。
群Ｂ：１以上のハロゲン原子を有してもよいＣ１−Ｃ４アルキル基、１以上のハロゲン原子を有してもよいＣ１−Ｃ４アルコキシ基、１以上のハロゲン原子を有してもよいＣ２−Ｃ５アルコキシカルボニル基、オキソ基及びハロゲン原子からなる群。
群Ｃ：群Ｄより選ばれる１以上の置換基を有してもよいＣ３−Ｃ７シクロアルキル基、群Ｄより選ばれる１以上の置換基を有してもよいＣ６−Ｃ１０アリール基、群Ｄより選ばれる１以上の置換基を有してもよいＣ６−Ｃ１０アリールオキシ基、群Ｄより選ばれる１以上の置換基を有してもよい（Ｃ６−Ｃ１０アリール）Ｃ１−Ｃ４アルコキシ基、群Ｄより選ばれる１以上の置換基を有してもよい５−１０員ヘテロアリール基、１以上のハロゲン原子を有してもよいＣ１−Ｃ４アルコキシ基、ハロゲン原子、ヒドロキシ基、ニトロ基、シアノ基、ホルミル基、１以上のハロゲン原子を有してもよいＣ２−Ｃ５アルコキシカルボニル基、ＮＲ¹⁸Ｒ¹⁹及びＣ（Ｏ）ＮＲ¹⁸Ｒ¹⁹からなる群。
群Ｄ：１以上のハロゲン原子を有してもよいＣ１−Ｃ４鎖式炭化水素基、１以上のハロゲン原子を有してもよいＣ１−Ｃ４アルコキシ基、１以上のハロゲン原子を有してもよいＣ１−Ｃ４アルコキシアルキル基、１以上のハロゲン原子を有してもよいＣ１−Ｃ４アルキルチオ基、１以上のハロゲン原子を有してもよいＣ１−Ｃ４アルキルスルフィニル基、１以上のハロゲン原子を有してもよいＣ１−Ｃ４アルキルスルホニル基、１以上のハロゲン原子を有してもよいＣ２−Ｃ５アルコキシカルボニル基、ヒドロキシ基、ニトロ基、シアノ基、ホルミル基、カルボキシ基、ＮＲ²⁰Ｒ²¹、ＣＯＮＲ²⁰Ｒ²¹及びハロゲン原子からなる群｛Ｒ²⁰及びＲ²¹は、各々独立して、１以上のハロゲン原子を有してもよいＣ１−Ｃ６アルキル基又は水素原子を表す｝〕
で示される化合物又はその塩（以下、本化合物と記す）と不活性担体とを含有する有害節足動物防除組成物（以下、本発明組成物と記す）。
〔２〕 前記式（Ｉ）において、
Ｒ¹が、群Ａ３より選ばれる１以上の置換基を有してもよいＣ１−Ｃ６鎖式炭化水素基、ヒドロキシ基を有してもよいＣ３−Ｃ６シクロアルキル基、フェニル基、ピリジル基｛該フェニル基及び該ピリジル基は、ハロゲン原子及びＣ１−Ｃ４アルキル基からなる群より選ばれる１以上の置換基を有してもよい｝、アゼチジニル基、ピロリジニル基、又はピペリジル基｛該アゼチジニル基、該ピロリジニル基、及び該ピペリジル基は、１以上のハロゲン原子を有してもよいＣ１−Ｃ４アルキル基及び１以上のハロゲン原子を有してもよいＣ２−Ｃ５アルコキシカルボニル基からなる群より選ばれる１以上の置換基を有してもよい｝であり、
Ｇ¹がＣＨであり、
Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ｒ⁶、Ｒ⁷、Ｒ⁸、Ｒ⁹、Ｒ¹⁰、Ｒ¹¹、Ｒ¹²、及びＲ¹³が、各々独立して、群Ｆより選ばれる１以上の置換基を有してもよいフェニル基、群Ｆより選ばれる１以上の置換基を有してもよいナフチル基、群Ｇより選ばれる１以上の置換基を有してもよいＣ１−Ｃ２鎖式炭化水素基又は水素原子であり、
Ｘが、水素原子である請求項１に記載の有害節足動物防除組成物。
群Ａ３：メトキシ基、アミノ基、メチルアミノ基、ジメチルアミノ基、テトラヒドロフラニル基、テトラヒドロピラニル基、群Ｆより選ばれる１以上の置換基を有してもよいフェニル基、及び群Ｆより選ばれる１以上の置換基を有してもよいピリジル基からなる群。
群Ｆ：ハロゲン原子、メチル基、トリフルオロメチル基、メトキシ基、トリフルオロメトキシ基、ヒドロキシ基、アミノ基、メチルアミノ基、ジメチルアミノ基、ニトロ基、シアノ基、及びホルミル基からなる群。
群Ｇ：群Ｆより選ばれる１以上の置換基を有してもよいフェニル基、及び群Ｆより選ばれる１以上の置換基を有してもよいナフチル基からなる群である〔１〕記載の有害節足動物防除組成物。
〔３〕 〔１〕又は〔２〕いずれかに記載の有害節足動物防除組成物を有害節足動物又は有害節足動物の生息場所に施用する有害節足動物の防除方法。
〔４〕 式（ＩＩ）

〔式中、
Ｒ^1xは、群Ａ３より選ばれる１以上の置換基を有してもよいＣ１−Ｃ６鎖式炭化水素基、ヒドロキシ基を有してもよいＣ３−Ｃ６シクロアルキル基、フェニル基、又はピリジル基｛該フェニル基及び該ピリジル基は、１以上のハロゲン原子又はメチル基を有してもよい｝を表し、
Ｇ^2xは、ＣＲ^2xＲ^3xを表し、
Ｇ^3xは、単結合又はＣＲ^4xＲ^5xを表し、
Ｇ^4xは、単結合又はＣＲ^6xＲ^7xを表し、
Ｇ^5xは、単結合又はＣＲ^8xＲ^9xを表し、
Ｇ^6xは、単結合又はＣＲ^10xＲ^11xを表し、
Ｇ^7xは、ＣＲ^12xＲ^13xを表し、
Ｒ^2x、Ｒ^3x、Ｒ^4x、Ｒ^5x、Ｒ^6x、Ｒ^7x、Ｒ^8x、Ｒ^9x、Ｒ^10x、Ｒ^11x、Ｒ^12x、及びＲ^13xは、各々独立して、群Ｆより選ばれる１以上の置換基を有してもよいフェニル基、群Ｆより選ばれる１以上の置換基を有してもよいナフチル基、群Ｇより選ばれる１以上の置換基を有してもよいＣ１−Ｃ２鎖式炭化水素基又は水素原子を表す。
群Ａ３：メトキシ基、アミノ基、メチルアミノ基、ジメチルアミノ基、テトラヒドロフラニル基、テトラヒドロピラニル基、群Ｆより選ばれる１以上の置換基を有してもよいフェニル基、及び群Ｆより選ばれる１以上の置換基を有してもよいピリジル基からなる群。
群Ｆ：ハロゲン原子、メチル基、トリフルオロメチル基、メトキシ基、トリフルオロメトキシ基、ヒドロキシ基、アミノ基、メチルアミノ基、ジメチルアミノ基、ニトロ基、シアノ基、ホルミル基からなる群。
群Ｇ：群Ｆより選ばれる１以上の置換基を有してもよいフェニル基、及び群Ｆより選ばれる１以上の置換基を有してもよいナフチル基からなる群。〕
で示される化合物又はその塩。 [1] Formula (I)

[Where,
R ¹ is a C1-C8 chain hydrocarbon group which may have one or more substituents selected from group A1, and a C3-C7 cycloalkyl which may have one or more substituents selected from group A2. A group, a phenyl group optionally having one or more substituents selected from group A2, a 5-10 membered heteroaryl group optionally having one or more substituents selected from group A2, or a group B Represents a 3- to 7-membered saturated heterocyclic group optionally having one or more substituents,
G ¹ represents CH, C (CH ₃ ), or C (CN);
G ² represents CR ² R ³ ,
G ³ represents a single bond or CR ⁴ R ⁵ ,
G ⁴ represents a single bond or CR ⁶ R ⁷ ,
G ⁵ represents a single bond or CR ⁸ R ⁹ ;
G ⁶ represents a single bond or CR ¹⁰ R ¹¹ ,
G ⁷ represents CR ¹² R ¹³ ,
R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ , R ¹² , and R ¹³ are each independently a halogen atom, nitro group, cyano Group, formyl group, NR ¹⁸ R ¹⁹ {R ¹⁸ and R ¹⁹ each independently represents a C1-C6 alkyl group optionally having one or more halogen atoms or a hydrogen atom}, selected from group C A C1-C8 chain hydrocarbon group which may have one or more substituents, a C1-C4 alkoxy group which may have one or more halogen atoms, and one or more substituents selected from group D An optionally substituted C6-C10 aryl group, a C6-C10 aryloxy group optionally having one or more substituents selected from group D, and one or more substituents selected from group D; 10-membered heteroaryl group, C3-C7 cycloalkyl optionally having one or more substituents selected from group D It represents a group or a hydrogen atom,
X represents a hydrogen atom, a halogen atom, a C1-C3 chain hydrocarbon group, a cyano group, a formyl group, a hydroxy group, or a C1-C3 alkoxy group.
Group A1: A C3-C7 cycloalkyl group optionally having one or more substituents selected from Group A2, a phenyl group optionally having one or more substituents selected from Group A2, and a group A2 5-10 membered heteroaryl group optionally having one or more substituents, 3-7 membered saturated heterocyclic group optionally having one or more substituents from group B, halogen atom, one or more halogens A group consisting of a C1-C4 alkoxy group optionally having an atom, a hydroxy group, a C2-C5 alkoxycarbonyl group optionally having one or more halogen atoms, NR ¹⁴ R ¹⁵ and C (O) NR ¹⁴ R ¹⁵ {R ¹⁴ and R ¹⁵ each independently represents a C1-C6 alkyl group which may have one or more halogen atoms or a hydrogen atom}.
Group A2: halogen atom, C1-C4 alkyl group optionally having one or more halogen atoms, C1-C4 alkoxy group optionally having one or more halogen atoms, hydroxy group, nitro group, cyano group, formyl Group, C2-C5 alkoxycarbonyl group optionally having one or more halogen atoms, a group consisting of NR ¹⁶ R ¹⁷ and C (O) NR ¹⁶ R ¹⁷ {R ¹⁶ and R ¹⁷ are each independently 1 Represents a C1-C6 alkyl group or a hydrogen atom which may have the above halogen atoms}.
Group B: C1-C4 alkyl group which may have one or more halogen atoms, C1-C4 alkoxy group which may have one or more halogen atoms, C2- which may have one or more halogen atoms A group consisting of a C5 alkoxycarbonyl group, an oxo group and a halogen atom.
Group C: C3-C7 cycloalkyl group optionally having one or more substituents selected from Group D, C6-C10 aryl group optionally having one or more substituents selected from Group D, Group D A C6-C10 aryloxy group optionally having one or more substituents selected from the above, a (C6-C10 aryl) C1-C4 alkoxy group optionally having one or more substituents selected from the group D, a group 5-10 membered heteroaryl group optionally having one or more substituents selected from D, C1-C4 alkoxy group optionally having one or more halogen atoms, halogen atom, hydroxy group, nitro group, cyano A group consisting of a group, a formyl group, a C2-C5 alkoxycarbonyl group optionally having one or more halogen atoms, NR ¹⁸ R ¹⁹ and C (O) NR ¹⁸ R ¹⁹ .
Group D: C1-C4 chain hydrocarbon group which may have one or more halogen atoms, C1-C4 alkoxy group which may have one or more halogen atoms, or one or more halogen atoms Good C1-C4 alkoxyalkyl group, C1-C4 alkylthio group optionally having one or more halogen atoms, C1-C4 alkylsulfinyl group optionally having one or more halogen atoms, having one or more halogen atoms C1-C4 alkylsulfonyl group which may have one or more, C2-C5 alkoxycarbonyl group which may have one or more halogen atoms, hydroxy group, nitro group, cyano group, formyl group, carboxy group, NR ²⁰ R ²¹ , CONR ²⁰ R ²¹ and the group {R ²⁰ and R ²¹ consisting of a halogen atom, each independently, 1 or more halogen atoms or C1-C6 alkyl group or a hydrogen atom may have a Be}]
Or a salt thereof (hereinafter referred to as the present compound) and an inert arthropod control composition (hereinafter referred to as the composition of the present invention).
[2] In the formula (I),
R ¹ is a C1-C6 chain hydrocarbon group that may have one or more substituents selected from group A3, a C3-C6 cycloalkyl group that may have a hydroxy group, a phenyl group, a pyridyl group { The phenyl group and the pyridyl group may have one or more substituents selected from the group consisting of a halogen atom and a C1-C4 alkyl group}, an azetidinyl group, a pyrrolidinyl group, or a piperidyl group {the azetidinyl group, The pyrrolidinyl group and the piperidyl group are selected from the group consisting of a C1-C4 alkyl group which may have one or more halogen atoms and a C2-C5 alkoxycarbonyl group which may have one or more halogen atoms. Which may have one or more substituents}
G ¹ is CH,
R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ , R ¹² , and R ¹³ are each independently one or more selected from group F A phenyl group which may have one of the substituents, a naphthyl group which may have one or more substituents selected from group F, and a C1-C2 which may have one or more substituents selected from group G A chain hydrocarbon group or a hydrogen atom,
The harmful arthropod control composition according to claim 1, wherein X is a hydrogen atom.
Group A3: selected from methoxy group, amino group, methylamino group, dimethylamino group, tetrahydrofuranyl group, tetrahydropyranyl group, phenyl group optionally having one or more substituents selected from group F, and group F A group consisting of a pyridyl group optionally having one or more substituents.
Group F: Group consisting of halogen atom, methyl group, trifluoromethyl group, methoxy group, trifluoromethoxy group, hydroxy group, amino group, methylamino group, dimethylamino group, nitro group, cyano group, and formyl group.
Group G: a group consisting of a phenyl group optionally having one or more substituents selected from Group F and a naphthyl group optionally having one or more substituents selected from Group F [1] Harmful arthropod control composition.
[3] A method for controlling harmful arthropods, wherein the composition for controlling harmful arthropods according to any one of [1] or [2] is applied to harmful arthropods or habitats of harmful arthropods.
[4] Formula (II)

[Where,
R ^1x is a C1-C6 chain hydrocarbon group that may have one or more substituents selected from group A3, a C3-C6 cycloalkyl group that may have a hydroxy group, a phenyl group, or a pyridyl group. {The phenyl group and the pyridyl group may have one or more halogen atoms or methyl groups};
G ^2x represents CR ^2x R ^3x
G ^3x represents a single bond or CR ^4x R ^5x ,
G ^4x represents a single bond or CR ^6x R ^7x ,
G ^5x represents a single bond or CR ^8x R ^9x ,
G ^6x represents a single bond or CR ^10x R ^11x ,
G ^7x represents CR ^12x R ^13x
R ^2x , R ^3x , R ^4x , R ^5x , R ^6x , R ^7x , R ^8x , R ^9x , R ^10x , R ^11x , R ^12x , and R ^13x are each independently one or more selected from group F A phenyl group which may have one of the substituents, a naphthyl group which may have one or more substituents selected from group F, and a C1-C2 which may have one or more substituents selected from group G Represents a chain hydrocarbon group or a hydrogen atom.
Group A3: selected from methoxy group, amino group, methylamino group, dimethylamino group, tetrahydrofuranyl group, tetrahydropyranyl group, phenyl group optionally having one or more substituents selected from group F, and group F A group consisting of a pyridyl group optionally having one or more substituents.
Group F: Group consisting of halogen atom, methyl group, trifluoromethyl group, methoxy group, trifluoromethoxy group, hydroxy group, amino group, methylamino group, dimethylamino group, nitro group, cyano group, formyl group.
Group G: A group consisting of a phenyl group which may have one or more substituents selected from Group F and a naphthyl group which may have one or more substituents selected from Group F. ]
Or a salt thereof.

  The composition of the present invention has excellent control activity against harmful arthropods.

  The compound may have one or more stereoisomers. Examples of stereoisomers include enantiomers and diastereomers. Diastereomers include cycloalkyl cis- and trans-isomers. The present invention includes each stereoisomer and any ratio of stereoisomer mixtures.

  The salt of the present compound is produced by mixing the present compound with an inorganic acid such as hydrogen chloride, phosphoric acid or sulfuric acid, or an organic acid such as acetic acid, trifluoroacetic acid, benzoic acid or p-toluenesulfonic acid. .

The substituent in the present invention will be described.
“Halogen atom” represents a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.
In the case of having two or more halogen atoms, these halogen atoms may be the same as or different from each other.
In this specification, the expression “CX-CY” means that the number of carbon atoms is X to Y. For example, the expression “C1-C4” means that the number of carbon atoms is 1 to 4.
The “chain hydrocarbon group” represents an alkyl group, an alkenyl group or an alkynyl group. When the “chain hydrocarbon group” is an alkenyl group or an alkynyl group, the number of carbon atoms means 2 or more.
Examples of the “alkyl group” include methyl group, ethyl group, propyl group, isopropyl group, 1,1-dimethylpropyl group, 1,2-dimethylpropyl group, 1-ethylpropyl group, butyl group, sec-butyl group, Examples thereof include a tert-butyl group, a pentyl group, a hexyl group, and an octyl group.
Examples of the “alkenyl group” include a vinyl group, 1-propenyl group, 2-propenyl group, 1-methyl-1-propenyl group, 1-methyl-2-propenyl group, 1,2-dimethyl-1-propenyl group, Examples include 1-ethyl-2-propenyl group, 3-butenyl group, 4-pentenyl group, 5-hexenyl group, and 7-octenyl group.
Examples of the “alkynyl group” include ethynyl group, 1-propynyl group, 2-propynyl group, 1-methyl-2-propynyl group, 1,1-dimethyl-2-propynyl group, 1-ethyl-2-propynyl group, Examples include 2-butynyl group, 4-pentynyl group, 5-hexynyl group and 7-octynyl group.
The “C3-C7 cycloalkyl group” represents, for example, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, or a cycloheptyl group.
“C2-C5 alkoxycarbonyl group” means a carbonyl group to which a C1-C4 alkoxy group is bonded, and examples thereof include a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, and a butoxycarbonyl group.
Examples of the “5-10 membered heteroaryl group” include pyrrolyl, furyl, thienyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl Group, pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group and quinolyl group.
Examples of the “3-7 membered saturated heterocyclic group” include aziridinyl group, azetidinyl group, pyrrolidinyl group, piperidyl group, azepanyl group, pyrazolidinyl group, imidazolidinyl group, oxetanyl group, tetrahydrofuranyl group, tetrahydropyranyl group, tetrahydrothienyl group. Group, oxazolidinyl group, thiazolidinyl group, isoxazolidinyl group, morpholinyl group, thiomorpholinyl group, 1,2-oxazinyl group, 1,3-oxazinyl group, 1,3-thiazinyl group, piperazinyl group, hexahydropyridazinyl group Group, hexahydropyrimidinyl group and 1,4-thiazepanyl group. As the 3-7-membered saturated heterocyclic group, a tetrahydrofuranyl group is preferable.
Examples of the “C6-C10 aryl group” include a phenyl group, an indanyl group, a tetrahydronaphthyl group, and a naphthyl group.

  "(C6-C10 aryl) C1-C4 alkoxy group optionally having one or more substituents selected from group D" means a C6-C10 aryl part of (C6-C10 aryl) C1-C4 alkoxy group. It represents a group to which one or more substituents selected from group D may be bonded, and examples thereof include a 2-fluorophenylmethoxy group and a 3-methoxynaphthylethoxy group.

The following compounds are mentioned as an aspect of this compound.
[Aspect 1] In this compound, R ¹ may have one or more substituents selected from group A3, a C1-C6 chain hydrocarbon group, and one or more hydroxy groups. A C6 cycloalkyl group, a phenyl group, a pyridyl group (the phenyl group and the pyridyl group may have one or more substituents selected from the group consisting of a halogen atom and a methyl group), an azetidinyl group, a pyrrolidinyl group, Or a piperidyl group {the azetidinyl group, the pyrrolidinyl group, and the piperidyl group may have a C1-C4 alkyl group that may have one or more halogen atoms and a C2-C5 alkoxy that may have one or more halogen atoms. A compound that may have one or more substituents selected from the group consisting of carbonyl groups;
[Aspect 2] In this compound, R ¹ may have one or more substituents selected from group A3, a C1-C6 chain hydrocarbon group, and one or more hydroxy groups. A compound that is a C6 cycloalkyl group, a phenyl group, or a pyridyl group (the phenyl group and the pyridyl group may have one or more substituents selected from the group consisting of a halogen atom and a methyl group);
[Aspect 3] A compound in which R ¹ is a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from group A3;
[Aspect 4] A compound in which R ¹ is a C3-C6 cycloalkyl group optionally having one or more hydroxy groups in the present compound;
[Aspect 5] In this compound, R ¹ may have a phenyl group or a pyridyl group {the phenyl group and the pyridyl group may have one or more substituents selected from the group consisting of a halogen atom and a methyl group. } A compound that is
[Aspect 6] In the present compound, R ¹ has a C1-C4 alkoxy group, NR ¹⁴ R ¹⁵ , a phenyl group optionally having one or more C1-C4 alkyl groups, and one or more C1-C4 alkyl groups. A C1-C8 alkyl group optionally having one or more substituents selected from the group consisting of 3-7 membered saturated heterocyclic groups,
A C3-C6 cycloalkyl group optionally having one or more hydroxy groups,
A phenyl group which may have one or more substituents selected from the group consisting of a halogen atom and a C1-C4 alkyl group,
3-7 member which may have one or more substituents selected from the group consisting of a pyridyl group which may have one or more C1-C4 alkyl groups or a C1-C4 alkyl group and a C2-C5 alkoxycarbonyl group A compound which is a saturated heterocyclic group;
[Aspect 7] In this compound, R ¹ has a C1-C4 alkoxy group, NR ¹⁴ R ¹⁵ , a phenyl group optionally having one or more C1-C4 alkyl groups, and one or more C1-C4 alkyl groups. A C1-C8 alkyl group optionally having one or more substituents selected from the group consisting of 3-7 membered saturated heterocyclic groups,
A C3-C6 cycloalkyl group optionally having one or more hydroxy groups,
A phenyl group which may have one or more substituents selected from the group consisting of a halogen atom and a C1-C4 alkyl group,
Or a compound that is a pyridyl group optionally having one or more C1-C4 alkyl groups;
[Aspect 8] In the present compound, R ¹ has a C1-C4 alkoxy group, NR ¹⁴ R ¹⁵ , a phenyl group optionally having one or more C1-C4 alkyl groups, and one or more C1-C4 alkyl groups. A compound that is a C1-C8 alkyl group optionally having one or more substituents selected from the group consisting of 3-7-membered saturated heterocyclic groups;
[Aspect 9] In this compound, R ¹ is a phenyl group which may have one or more substituents selected from the group consisting of a halogen atom and a C1-C4 alkyl group;
[Aspect 10] A compound in which R ¹ is a pyridyl group optionally having one or more C1-C4 alkyl groups;

[Aspect 11] A compound in which X is a hydrogen atom in the present compound;
[Aspect 12] A compound in which G ¹ is CH in the present compound;

[Aspect 13] In this compound, X is a hydrogen atom, G ¹ is CH, R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ , R ¹² , and R ¹³ may each independently have a phenyl group that may have one or more substituents selected from group F, or one or more substituents selected from group F. A naphthyl group, a C1-C2 chain hydrocarbon group which may have one or more substituents selected from group G, or a compound which is a hydrogen atom;
[Aspect 14] In the present compound, X is a hydrogen atom, G ¹ is CH, G ⁶ is a single bond, R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹² , and R ¹³ each independently have a phenyl group that may have one or more substituents selected from group F, and one or more substituents selected from group F. A naphthyl group, a C1-C2 chain hydrocarbon group which may have one or more substituents selected from group G or a hydrogen atom;
[Aspect 15] In this compound, X is a hydrogen atom, G ¹ is CH, G ⁵ and G ⁶ are single bonds, R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ¹² , and R ¹³ are each independently a phenyl group that may have one or more substituents selected from group F, or a naphthyl that may have one or more substituents selected from group F A group, a C1-C2 chain hydrocarbon group which may have one or more substituents selected from group G or a hydrogen atom;
[Aspect 16] In the present compound, X is a hydrogen atom, G ¹ is CH, G ⁴ , G ⁵ and G ⁶ are single bonds, and R ² , R ³ , R ⁴ , R ⁵ , R ¹² And R ¹³ are each independently a phenyl group optionally having one or more substituents selected from group F, a naphthyl group optionally having one or more substituents selected from group F, group A compound which is a C1-C2 chain hydrocarbon group or hydrogen atom which may have one or more substituents selected from G;
[Aspect 17] In the present compound, X is a hydrogen atom, G ¹ is CH, G ³ , G ⁴ , G ⁵ and G ⁶ are single bonds, R ² , R ³ , R ¹² , and R ¹³ are each independently selected from a phenyl group optionally having one or more substituents selected from group F, a naphthyl group optionally having one or more substituents selected from group F, or a group G. A C1-C2 chain hydrocarbon group which may have one or more substituents or a hydrogen atom;

[Aspect 18] In this compound, X is a hydrogen atom, G ¹ is CH, G ² , G ³ , G ⁴ , G ⁵ and G ⁶ are single bonds, and R ¹² and R ¹³ are each Independently, a phenyl group optionally having one or more substituents selected from group F, a naphthyl group optionally having one or more substituents selected from group F, one or more selected from group G A compound that is a C1-C2 chain hydrocarbon group or a hydrogen atom which may have a substituent;
[Aspect 19] In this compound, X is a hydrogen atom, G ¹ is CH, G ⁶ is a single bond, G ² , G ³ , G ⁴ and G ⁵ are CH ₂ , R ¹² and From R ¹³ each independently a phenyl group optionally having one or more substituents selected from group F, a naphthyl group optionally having one or more substituents selected from group F, from group G A compound that is a C1-C2 chain hydrocarbon group or a hydrogen atom which may have one or more selected substituents;
[Aspect 21] In this compound, X is a hydrogen atom, G ¹ is CH, G ⁵ and G ⁶ are single bonds, G ² , G ³ , and G ⁴ are CH ₂ , R ¹² And R ¹³ each independently represents a phenyl group which may have one or more substituents selected from group F, a naphthyl group which may have one or more substituents selected from group F, group G A compound which is a C1-C2 chain hydrocarbon group or hydrogen atom which may have one or more substituents selected from;
[Aspect 22] In the present compound, X is a hydrogen atom, G ¹ is CH, G ⁴ , G ⁵ and G ⁶ are single bonds, G ² and G ³ are CH ₂ , R ¹² and From R ¹³ each independently a phenyl group optionally having one or more substituents selected from group F, a naphthyl group optionally having one or more substituents selected from group F, from group G A compound that is a C1-C2 chain hydrocarbon group or a hydrogen atom which may have one or more selected substituents;
[Aspect 23] In this compound, X is a hydrogen atom, G ¹ is CH, G ³ , G ⁴ , G ⁵ and G ⁶ are single bonds, G ² is CH ₂ , R ¹² and From R ¹³ each independently a phenyl group optionally having one or more substituents selected from group F, a naphthyl group optionally having one or more substituents selected from group F, from group G A compound that is a C1-C2 chain hydrocarbon group or a hydrogen atom which may have one or more selected substituents;

[Aspect 24] A compound in which X is a hydrogen atom, G ¹ is CH, and G ² , G ³ , G ⁴ , G ⁵ , G ⁶ and G ⁷ are CH ₂ in the present compound;
[Aspect 25] A compound in which X is a hydrogen atom, G ¹ is CH, G ⁶ is a single bond, and G ² , G ³ , G ⁴ , G ⁵ and G ⁷ are CH ₂ in this compound. ;
[Aspect 26] A compound in which X is a hydrogen atom, G ¹ is CH, G ⁵ and G ⁶ are single bonds, and G ² , G ³ , G ⁴ and G ⁷ are CH ₂ in this compound. ;
[Aspect 27] A compound wherein X is a hydrogen atom, G ¹ is CH, G ⁴ , G ⁵ and G ⁶ are single bonds, and G ² , G ³ and G ⁷ are CH ₂ ;
[Aspect 28] In this compound, X is a hydrogen atom, G ¹ is CH, G ³ , G ⁴ , G ⁵ and G ⁶ are single bonds, and G ² and G ⁷ are CH ₂ ;

[Aspect 29] In any one of aspects 11 to 28, R ¹ has a C1-C6 chain hydrocarbon group which may have one or more substituents selected from group A3, and has one or more hydroxy groups. C3-C6 cycloalkyl group, phenyl group, pyridyl group {the phenyl group and the pyridyl group may have one or more substituents selected from the group consisting of a halogen atom and a methyl group}, An azetidinyl group, a pyrrolidinyl group, or a piperidyl group {the azetidinyl group, the pyrrolidinyl group, and the piperidyl group have a C1-C4 alkyl group that may have one or more halogen atoms, and one or more halogen atoms A compound that may have one or more substituents selected from the group consisting of optionally C2-C5 alkoxycarbonyl groups;
[Aspect 30] In any one of Aspects 11 to 28, R ¹ has a C1-C6 chain hydrocarbon group which may have one or more substituents selected from Group A3, and has one or more hydroxy groups. A C3-C6 cycloalkyl group, a phenyl group, or a pyridyl group (the phenyl group and the pyridyl group may have one or more substituents selected from the group consisting of a halogen atom and a methyl group) A compound which is
[Aspect 31] The compound according to any one of Aspects 11 to 28, wherein R ¹ is a C1-C6 chain hydrocarbon group which may have one or more substituents selected from group A3.
[Aspect 32] The compound according to any one of Aspects 11 to 28, wherein R ¹ is a C3-C6 cycloalkyl group optionally having one or more hydroxy groups.
[Aspect 33] In any one of Aspects 11 to 28, R ¹ is a phenyl group or a pyridyl group {wherein the phenyl group and the pyridyl group are selected from the group consisting of a halogen atom and a methyl group. Which may have a compound.
[Aspect 34] In any one of aspects 11 to 28, R ¹ is a C1-C4 alkoxy group, NR ¹⁴ R ¹⁵ , a phenyl group optionally having one or more C1-C4 alkyl groups, and one or more C1- A C1-C8 alkyl group which may have one or more substituents selected from the group consisting of 3-7 membered saturated heterocyclic groups which may have a C4 alkyl group,
A C3-C7 cycloalkyl group optionally having one or more hydroxy groups,
A phenyl group which may have one or more substituents selected from the group consisting of a halogen atom and a C1-C4 alkyl group,
3-7 member which may have one or more substituents selected from the group consisting of a pyridyl group which may have one or more C1-C4 alkyl groups or a C1-C4 alkyl group and a C2-C5 alkoxycarbonyl group A compound which is a saturated heterocyclic group.
[Aspect 35] In any one of aspects 11 to 28, R ¹ is a C1-C4 alkoxy group, NR ¹⁴ R ¹⁵ , a phenyl group optionally having one or more C1-C4 alkyl groups, and one or more C1- A C1-C8 alkyl group which may have one or more substituents selected from the group consisting of 3-7 membered saturated heterocyclic groups which may have a C4 alkyl group,
A C3-C7 cycloalkyl group optionally having one or more hydroxy groups,
A phenyl group which may have one or more substituents selected from the group consisting of a halogen atom and a C1-C4 alkyl group,
Or the compound which is a pyridyl group which may have one or more C1-C4 alkyl groups.
In any of the [Mode 36] embodiment 11 embodiment 28, R ¹ is, C1-C4 alkoxy group, NR ¹⁴ R ^15, 1 or more C1-C4 phenyl group which may have an alkyl group and one or more C1 A compound which is a C1-C8 alkyl group which may have one or more substituents selected from the group consisting of a 3-7 membered saturated heterocyclic group which may have a -C4 alkyl group.
[Aspect 37] The compound according to any one of Aspects 11 to 28, wherein R ¹ is a phenyl group which may have one or more substituents selected from the group consisting of a halogen atom and a C1-C4 alkyl group.
[Aspect 38] The compound according to any one of Aspects 11 to 28, wherein R ¹ is a pyridyl group optionally having one or more C1-C4 alkyl groups.

[Aspect 39] In the present compound, G ¹ is CH, G ² is CH ₂ , G ⁷ is CHR ¹² , G ³ , G ⁴ , G ⁵ and G ⁶ are single bonds, and R ¹² Is a C1-C8 alkyl group optionally having a hydrogen atom, a phenyl group or a phenyl group,
G ¹ is CH, G ² , G ³ , G ⁴ and G ⁷ are CH ₂ , G ⁵ and G ⁶ are single bonds, or G ¹ is CH, G ² , G ³ , G ⁴ , G ⁵ and G ⁷ are CH ₂ , G ⁶ is a single bond,
X is a hydrogen atom,
R ¹ may have a C1-C4 alkoxy group, NR ¹⁴ R ¹⁵ , a phenyl group optionally having one or more C1-C4 alkyl groups, and a 3-7 membered saturated optionally having one or more C1-C4 alkyl groups A C1-C8 alkyl group optionally having one or more substituents selected from the group consisting of heterocyclic groups,
A C3-C6 cycloalkyl group optionally having one or more hydroxy groups,
A phenyl group which may have one or more substituents selected from the group consisting of a halogen atom and a C1-C4 alkyl group,
3-7 member which may have one or more substituents selected from the group consisting of a pyridyl group which may have one or more C1-C4 alkyl groups or a C1-C4 alkyl group and a C2-C5 alkoxycarbonyl group A compound which is a saturated heterocyclic group.

[Aspect 40] In the present compound, G ¹ is CH, G ² is CH ₂ , G ⁷ is CHR ¹² , G ³ , G ⁴ , G ⁵ and G ⁶ are single bonds, and R ¹² Is a C1-C8 alkyl group optionally having a hydrogen atom, a phenyl group or a phenyl group, X is a hydrogen atom,
R ¹ may have one or more substituents selected from the group consisting of a C1-C4 alkoxy group, NR ¹⁴ R ¹⁵ , and a 3-7 membered saturated heterocyclic group,
A C3-C6 cycloalkyl group optionally having one or more hydroxy groups,
A phenyl group which may have one or more substituents selected from the group consisting of a halogen atom and a C1-C4 alkyl group,
3-7 member which may have one or more substituents selected from the group consisting of a pyridyl group which may have one or more C1-C4 alkyl groups or a C1-C4 alkyl group and a C2-C5 alkoxycarbonyl group A compound which is a saturated heterocyclic group.

[Aspect 41] In the present compound, G ¹ is CH, G ² , G ³ , G ⁴ and G ⁷ are CH ₂ , G ⁵ and G ⁶ are single bonds,
X is a hydrogen atom,
R ¹ is NR ¹⁴ R ¹⁵ , and a C1-C8 alkyl group which may have one or more substituents selected from the group consisting of a 3-7 membered saturated heterocyclic group,
A C3-C6 cycloalkyl group optionally having one or more hydroxy groups,
One or more substituents selected from the group consisting of a phenyl group or a C1-C4 alkyl group and a C2-C5 alkoxycarbonyl group which may have one or more substituents selected from the group consisting of a halogen atom and a C1-C4 alkyl group The compound which is a 3-7 membered saturated heterocyclic group which may have a group.

[Aspect 42] In the present compound, G ¹ is CH, G ² , G ³ and G ⁷ are CH ₂ , G ⁴ , G ⁵ and G ⁶ are single bonds,
X is a hydrogen atom,
R ¹ is NR ¹⁴ R ¹⁵ , and a C1-C8 alkyl group which may have one or more substituents selected from the group consisting of a 3-7 membered saturated heterocyclic group,
A C3-C6 cycloalkyl group optionally having one or more hydroxy groups,
One or more substituents selected from the group consisting of a phenyl group or a C1-C4 alkyl group and a C2-C5 alkoxycarbonyl group which may have one or more substituents selected from the group consisting of a halogen atom and a C1-C4 alkyl group The compound which is a 3-7 membered saturated heterocyclic group which may have a group.

[Aspect 43] In this compound, G ¹ is CH, G ² is CH ₂ , G ⁷ is CHR ¹² , G ³ , G ⁴ , G ⁵ and G ⁶ are single bonds, and R ¹² Is a C1-C8 alkyl group optionally having a hydrogen atom, a phenyl group or a phenyl group,
G ¹ is CH, G ² , G ³ , G ⁴ and G ⁷ are CH ₂ , G ⁵ and G ⁶ are single bonds, or G ¹ is CH, G ² , G ³ , G ⁴ , G ⁵ and G ⁷ are CH ₂ , G ⁶ is a single bond,
X is a hydrogen atom,
R ¹ has one or more substituents selected from the group consisting of a C1-C4 alkoxy group, NR ¹⁴ R ¹⁵ , a phenyl group which may have a C1-C4 alkyl group, and a 3-7-membered saturated heterocyclic group. An optionally substituted C1-C8 alkyl group,
A C3-C6 cycloalkyl group optionally having one or more hydroxy groups,
A phenyl group which may have one or more substituents selected from the group consisting of a halogen atom and a C1-C4 alkyl group,
Or the compound which is a pyridyl group which may have one or more C1-C4 alkyl groups.

[Aspect 44] A compound represented by formula (II).

The following are mentioned as an aspect of this invention composition.

The composition according to the invention, wherein the compound is a compound according to any one of [Aspect 1] to [Aspect 44].

  Next, the manufacturing method of this compound is demonstrated. This compound can be produced, for example, by the following production method.

［式中、記号は前記と同じ意味を表す。］
反応は、通常溶媒中で行われる。反応に用いられる溶媒としては、例えば、ｎ−ヘキサン、トルエン、キシレン等の炭化水素類（以下、炭化水素類と記す）、ジエチルエーテル、エチレングリコールジメチルエーテル、メチルｔｅｒｔ−ブチルエーテル、テトラヒドロフラン（以下、ＴＨＦと記す）等のエーテル類（以下、エーテル類と記す）、クロロホルム、クロロベンゼン等のハロゲン化炭化水素類（以下、ハロゲン化炭化水素類と記す）、ジメチルホルムアミド（以下、ＤＭＦと記す）等のアミド類（以下、アミド類と記す）、及び酢酸エチル等のエステル類（以下、エステル類と記す）等が挙げられる。
反応に用いられる縮合剤としては、例えば、プロピルホスホン酸無水物、ジシクロヘキシルカルボジイミド、１−エチル−３−（３−ジメチルアミノプロピル）カルボジイミド塩酸塩（以下、ＥＤＣと記す）、１Ｈ−ベンゾトリアゾール−１−イルオキシトリス（ジメチルアミノ）ホスホニウムヘキサフルオロホスフェート及びヘキサフルオロリン酸（ベンゾトリアゾール−１−イルオキシ）トリピロリジノホスホニウムが挙げられる。
反応に用いられる塩基としては、例えば炭酸ナトリウム、炭酸カリウム等のアルカリ金属炭酸塩類（以下、アルカリ金属炭酸塩類と記す）、トリエチルアミン、ジイソプロピルエチルアミン、ピリジン、４−（ジメチルアミノ）ピリジン等の有機塩基類（以下、有機塩基類と記す）が挙げられる。
反応は、化合物（Ａ）１モルに対して通常化合物（Ｂ）が１モル〜１０モルの割合で、縮合剤が１モル〜５モルの割合で、塩基が１モル〜１０モルの割合で用いられる。
反応には、さらに１−ヒドロキシベンゾトリアゾール、１−ヒドロキシ−７−アザベンゾトリアゾール、又はＮ−ヒドロキシコハク酸イミド等を加えてもよい。これらの化合物の使用量は、化合物（Ａ）１モルに対して、通常０．０１モル〜１モルであり、好ましくは０．０５モル〜０．２モルである。
反応時間は、通常、５分間〜７２時間の範囲である。反応温度は、通常、−２０℃〜１００℃の範囲である。
反応終了後は、反応混合物に水又は塩酸を加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、本化合物を単離することができる。
化合物（Ｂ）は、公知であるか、公知の方法に準じて製造することができる。 Manufacturing method 1
This compound comprises a compound represented by formula (A) (hereinafter referred to as compound (A)) and a compound represented by formula (B) (hereinafter referred to as compound (B)) as a base and a condensing agent. It can manufacture by making it react in presence.

[Wherein the symbols have the same meaning as described above. ]
The reaction is usually performed in a solvent. Examples of the solvent used for the reaction include hydrocarbons such as n-hexane, toluene and xylene (hereinafter referred to as hydrocarbons), diethyl ether, ethylene glycol dimethyl ether, methyl tert-butyl ether, tetrahydrofuran (hereinafter referred to as THF). Amides such as ethers (hereinafter referred to as ethers), halogenated hydrocarbons such as chloroform and chlorobenzene (hereinafter referred to as halogenated hydrocarbons), and dimethylformamide (hereinafter referred to as DMF). (Hereinafter referred to as amides) and esters such as ethyl acetate (hereinafter referred to as esters).
Examples of the condensing agent used in the reaction include propylphosphonic anhydride, dicyclohexylcarbodiimide, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (hereinafter referred to as EDC), 1H-benzotriazole-1 -Yloxytris (dimethylamino) phosphonium hexafluorophosphate and hexafluorophosphoric acid (benzotriazol-1-yloxy) tripyrrolidinophosphonium.
Examples of the base used in the reaction include alkali metal carbonates such as sodium carbonate and potassium carbonate (hereinafter referred to as alkali metal carbonates), organic bases such as triethylamine, diisopropylethylamine, pyridine, and 4- (dimethylamino) pyridine. (Hereinafter referred to as organic bases).
In the reaction, the compound (B) is usually used in a proportion of 1 mol to 10 mol, the condensing agent is used in a proportion of 1 mol to 5 mol, and the base is used in a proportion of 1 mol to 10 mol with respect to 1 mol of the compound (A). It is done.
In the reaction, 1-hydroxybenzotriazole, 1-hydroxy-7-azabenzotriazole, N-hydroxysuccinimide or the like may be further added. The amount of these compounds to be used is generally 0.01 mol to 1 mol, preferably 0.05 mol to 0.2 mol, per 1 mol of compound (A).
The reaction time is usually in the range of 5 minutes to 72 hours. The reaction temperature is usually in the range of -20 ° C to 100 ° C.
After completion of the reaction, this compound can be isolated by post-treatment such as addition of water or hydrochloric acid to the reaction mixture, extraction with an organic solvent, and drying and concentration of the organic layer.
Compound (B) is known or can be produced according to a known method.

［式中、記号は前記と同じ意味を表す。］
反応は、通常溶媒中で行われる。反応に用いられる溶媒としては、例えば、エーテル類、炭化水素類、ハロゲン化炭化水素類、エステル類、アセトニトリル、ブチロニトリル等のニトリル類（以下、ニトリル類と記す）及びこれらの混合物が挙げられる。
反応に用いられる塩基としては、例えば、アルカリ金属炭酸塩類、有機塩基類が挙げられる。
反応は、通常化合物（Ｃ）１モルに対して、化合物（Ｂ）が１〜１０モルの割合で、塩基が１〜５モルの割合で用いられる。
反応時間は、通常、５分間〜７２時間の範囲である。反応温度は、通常、−２０〜１００℃の範囲である。
反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、本化合物を単離することができる。 Manufacturing method 2
This compound can be produced by reacting a compound represented by formula (C) (hereinafter referred to as compound (C)) with compound (B) in the presence of a base.

[Wherein the symbols have the same meaning as described above. ]
The reaction is usually performed in a solvent. Examples of the solvent used in the reaction include ethers, hydrocarbons, halogenated hydrocarbons, esters, nitriles such as acetonitrile and butyronitrile (hereinafter referred to as nitriles), and mixtures thereof.
Examples of the base used for the reaction include alkali metal carbonates and organic bases.
In the reaction, the compound (B) is usually used in a proportion of 1 to 10 mol and the base is used in a proportion of 1 to 5 mol with respect to 1 mol of the compound (C).
The reaction time is usually in the range of 5 minutes to 72 hours. The reaction temperature is usually in the range of -20 to 100 ° C.
After completion of the reaction, the compound can be isolated by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.

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

［式中、Ｒ^aは、メチル基又はエチル基を表し、その他の記号は前記と同じ意味を表す。］
反応は、国際公開第２０１４／１１９６９６号に記載の方法に準じて実施することができる。 Reference manufacturing method 1
Compound (A) can be produced by hydrolyzing a compound represented by formula (D) (hereinafter referred to as compound (D)) in the presence of a base.

[Wherein, R ^a represents a methyl group or an ethyl group, and other symbols represent the same meaning as described above. ]
The reaction can be carried out according to the method described in International Publication No. 2014/119696.

［式中、記号は前記と同じ意味を表す。］ Reference production method 2
Compound (D) can also be produced according to the following scheme.

[Wherein the symbols have the same meaning as described above. ]

First, a step of producing a compound represented by formula (F) (hereinafter referred to as compound (F)) from a compound represented by formula (E) (hereinafter referred to as compound (E)) (hereinafter referred to as first step) Will be described.
Compound (F) can be produced by reacting compound (E) with an oxalate ester in the presence of a base.
Compound (E) is known or published in WO 2006/223884, Bioorganic and Medicinal Chemistry Letters, 20, 4918 (2010), Journal of Organic Chemistry, 80, 7212 (2015), or Journal of Medicinal Chemistry, 59, 282 (2016).

Next, the process for producing the compound (D) from the compound (F) (hereinafter referred to as the second process) will be described.
Compound (D) can be produced by reacting compound (F) with hydroxylamine.
The first step and the second step can be performed according to the method described in Bioorganic & Medicinal Chemistry Letters, 23, 273 (2013).

［式中、記号は前記と同じ意味を表す。］
反応は、国際公開第２０１４／１１９６９６号に記載の方法に準じて実施することができる。 Reference manufacturing method 3
Compound (C) can be produced by reacting compound (A) with a chlorinating agent.

[Wherein the symbols have the same meaning as described above. ]
The reaction can be carried out according to the method described in International Publication No. 2014/119696.

［式中、記号は前記と同じ意味を表す。］
反応は、Jounal of Chemical Society, Perkin Trans., 14, 1716 (2001)に記載の方法に準じて実施することができる。
化合物（Ｇ）は、公知であるか、Synlett, 558 (2009)、Organic Synthesis, 64, 44 (1986)、国際公開第2000/018706号、Tetrahedron letters, 49, 6794 (2008)、J. Org. Chem., 51, 4507 (1986)、Synthesis, 458 (1975) 、Angewandte Chemie, 53, 4154 (2014)、又はOrganic Letters, 15, 5810 (2013)に記載の方法に準じて製造することができる。
化合物（Ｈ）は、公知である。 Reference manufacturing method 4
Compound (D) is produced by reacting a compound represented by formula (G) (hereinafter referred to as compound (G)) with a compound represented by formula (H) (hereinafter referred to as compound (H)). You can also

[Wherein the symbols have the same meaning as described above. ]
The reaction can be carried out according to the method described in Journal of Chemical Society, Perkin Trans., 14, 1716 (2001).
Compound (G) is known or synlett, 558 (2009), Organic Synthesis, 64, 44 (1986), WO 2000/018706, Tetrahedron letters, 49, 6794 (2008), J. Org. Chem., 51, 4507 (1986), Synthesis, 458 (1975), Angelwandte Chemie, 53, 4154 (2014), or Organic Letters, 15, 5810 (2013).
Compound (H) is known.

［式中、記号は前記と同じ意味を表す。］
反応は、Europian Jounal of Organic Chemistry, 4852 (2006)、又は国際公開第２０１４／１１９６９６号記載の方法に準じて実施することができる。
化合物（Ｊ）は、公知である。 Reference production method 5
Compound (D) can also be produced by reacting compound (G) with a compound represented by formula (J) (hereinafter referred to as compound (J)).

[Wherein the symbols have the same meaning as described above. ]
The reaction can be performed according to the method described in Europian Jounal of Organic Chemistry, 4852 (2006) or International Publication No. 2014/119696.
Compound (J) is publicly known.

  Examples of harmful arthropods for which the composition of the present invention is effective include harmful insects and harmful mites. Specific examples of such harmful arthropods include the following.

  Hemiptera: Japanese brown planthopper (Laodelphax striatellus), Japanese brown planthopper (Nilaparvata lugens), white-tailed planthopper (Sogatella furcifera), corn planter (Peregrinus maidis), yellow-spotted plant (Javesella pellucida), black-tailed squid (Delphacidae); Nephotettix cincticeps, Nephotettix virescens, Nephotettix nigropictus, Recilia dorsalis, Eki ca ), Corn Leaf Hopper (Dalbulus maidis), Cofana spectra, etc., Cicadellidae; Mahanarva posticata, Mahanarva fimbriolata, etc., Cercopidae; Aphis fabae, soybean aphids (Aphis glycines), cotton aphids (Aphis gossypii), European apple aphids (Aphis pomi), snowy aphids (Aphis spiraecola), peach aphids (Myzus persicae), wheat arasi , Radish aphids (Brevicoryne brassicae), Dysaphis plantaginea, lip aphid erysimi, tulip beetle aphids (Macrosiphum euphorbiae), potato beetle aphids (Aulacorthum solani), aphids (Rhopalosiphum padi), corn aphid (Rhopalosiphum maidis), citrus aphid (Toxoptera citricidus), peach beetle (Hyalopterus pruni), hyena aphid (Melanaphis sacchari), brown aphid (Tetraneura nigriabdominalis), aphid (Ceratovacuna lanigera), apple aphid (Eriosoma lanigerum); Aphididae; Pecan leaf phylloxera (Phylloxera notabilis), Southern pecan leaf phylloxera (Phylloxera russellae), etc. Nephididae (Phylloxeridae); ); Rice stink bug (Scotinophara lurida), Malayan rice black bug (Scotinophara coarctata), blue stink bug (Nezara antennata), black spider stink bug (Eysarcoris aeneus), white spider stink bug (Eysarcoris ys) , Eryscalis annamita, Halyomorpha halys, Nezara viridula, Brown stink bug (Euschistus heros), Red banded stink bug (Piezodorus guildinii), Oebalus p (Pentatomidae); Burrower brown bug (Scaptocoris castanea), etc. (Cydnidae); Alydidae); Cletus punctiger, Leptoglossus australis, etc. (Coreidae); Naga (Blissus leucopterus) Lygaeidae; Trigonotylus caelestialium; Stenotus rubrovittatus; Stenodema calcarata; vaporariorum), tobacco whitefly (Bemisia tabaci), citrus whitefly (Dialeurodes citri), citrus whitefly (Aleurocanthus spiniferus), chaffed whitefly (Aleurocanthus camelliae), Hisakakifuta (Pealius eleyrodidae); Buprestidae (Abgrallaspis cyanophylli), Buprestidae (Aonidiella aurantii), Buprestidae (Diaspidiotus perniciosus), Scarab scale (Pseudaulacaspis pentagona), Buprestidae (Unaspis yanone) nsis), Nymphaensis scales (Unaspis citri), etc. (Diaspididae); Ruby beetles (Ceroplastes rubens), etc. Margarodidae, etc .; Phenacoccus solani, Phenacoccus solenopsis, Pterococcus kraunhiae, Planococcus comPlanoc , Pseudococcidae (Pseudococcus calceolariae), Pseudodococcus longispinus, Brevennia rehi, etc .; Pseudococcidae; Diaphorina citri Lami (Trioza erytreae), Pepper lice (Ccopsylla pyricuga), Pter psylla (Cacopsylla pyricola), Pear psylla (Cacopsylla pyricola), Pile psylla (Cacopsylla pyricola) Gumbai (Corythucha marmorata), Nashigumbai (Stephanitis nashi), Azalea Gumbai (Stephanitis pyrioides), etc .; Camidex lectularius, etc .;

  Lepidoptera: Green moth (Chilo suppressalis), Darkheaded stem borer (Chilo polychrysus), White stem borer (Scirpophaga innotata), Scirpophaga incertulas, Rupela albina, Cnaphalocrocisis media, Cnaphalocrocisis medis Hacasino maiga (Marasmia exigua), Watano maiga (Notarcha derogata), Awa no maiga (Ostrinia furnacalis), European corn borer (Ostrinia nubilalis), Hydraula undalis, Herpetogramma rel tueter, Rice case worms (Nymphula depunctalis), Sugarcane borer (Diatraea saccharalis), etc. (Crambidae); , Shiloi Spodoptera exigua, Mythimna separata, Mamestra brassicae, Sesamia inferens, Spodoptera mauritia, Naranga aenescens opt, Safoptera ma exempta), Agrotis ipsilon, Autographa nigrisigna, Inakinawaba (Plusia festucae), Soybean looper (Chrysodeixis includens), Trichoplusia spp., Heliothis virescens Helicoverpa armigera, Helicoverpa zea, and other Helicobelpa species, Velvetbean caterpillar (Anticarsia gemmatalis), Cotton leafworm (Alabama argillacea), Hop vine borer (Hydraecia immanis), etc. Noctuidae; Pae) and other white butterflies (Pieridae); Nashihimeshinsukui (Grapholita molesta); Crab (Adoxophyes honmai), Chamonaki (Homona magnanima), Midlekakumonmonki (Archips fuscocupreanus), Codlinga (Cydia pomonella), Kashashishinamaki (Tetramoera schistaceana), Bean Shoot Borer (Epinotia aporema) (Citrus fruit bore) Tortricidae; Toroptidae; Caloptilia theivora; Phyllonorycter ringoniella; Grascillariidae; Carposin sasakii; Carposinidae; Leucoptera Anemone family (Lynetia clerkella), Anemone family (Lyonetia prunifoliella), etc. (Lyonetiidae); Anthracite family (Lymantria dispar), such as Limantria genus; Plutella xylostella, etc. (Pluteliidae); Prunella (Anarsia lineatella), Prunella (Helcystogramma triannulellum), Cotton moth (Pectinophora gossypiella), Potato moth (Phthorimaea operculella); Arctiidae such as cunea; Castniidae such as Giant Sugarcane borer (Telchin licus); Castoridae such as Cosus insularis; Cosidae such as Ascotis selenaria ); Limacodidae such as Parasa lepida; Stahmmopodidae such as Stahmmopoda masinissa; Sphingidae such as Acherontia lachesis; Nokona feralis (Sesiidae); Hesperiidae such as Parnara guttata.

  Thysanoptera: Citrus thalis (Fripliniella occidentalis), Thrips palmi, Scirtothrips dorsalis, Thrips tabasa, Thrips tabasa, Thrips tabasa ), Thripidae such as Echinothrips americanus; Phlaeothripidae such as Haplothrips aculeatus.

  Diptera: Drosophila (Delia platura), onion flies (Delia antiqua), etc .; Anthomyiidae; Tomato leaf fly (Liriomyza sativae), bee leaf leaf fly (Liriomyza trifolii), leaf leaf fly (Chromatomyia horticola), and the like leaf fly family (Agromyzidae); ), Eggplant fly (Bactrocera latifrons), olive fruit fly (Bactrocera oleae), quinsland fruit fly (Bactrocera tryoni), Ceratitis capitata, etc. (Tephritidae); Hydrellia philippina, Hydrellia sasakii, and other species (Ephydridae); Drosophila suzukii, and other species; Drosophila suzukii; (Clogmia albipunctata) and other butterflies; Bradysia difformis and other species of black flies (Sciaridae); Diopsidae such as macrophthalma; Tipulidae such as Tipula aino, Common cranefly (Tipula oleracea), European cranefly (Tipula paludosa).

  Coleoptera: Western corn root worm (Diabrotica virgifera virgifera), Southern corn root worm (Diabrotica undecimpunctata howardi), Northern corn root worm (Diabrotica barberi), Mexican corn root worm (Diabrotica virgifera zeae), Banded cucumber beetle Diabrotica balteata), Cucurbit Beetle (Diabrotica speciosa), bean leaf beetle (Cerotoma trifurcata), tiger beetle (Oulema melanopus), cucumber leaf beetle (Aulacophora femoralis), pheasant leaf beetle (Phyllotreta striolata) et black flea beetle (Phyllotreta pusilla), Cabbage stem flea beetle (Psylliodes chrysocephala), Colorado potato beetle (Leptinotarsa decemlineata), rice beetle (Oulema oryzae), grape colaspis (Colaspis brunnea), corn flarebi Toru (Chaetocnema pulicaria), sweet potato beetle (Chaetocnema confi), potato flare beetle (Epitrix cucumeris), rice beetle (Dicladispa armigera), Grape Colaspis (Colaspis brunnea), southern corn leaf denetle (Sweet corn leaf denticle) Laccoptera quadrimacu), Chrysomelidae such as Epitrix hirtipennis; Seedcorn beetle (Stenolophus lecontei), Slender seedcorn beetle (Clivina impressifrons); Carabidae; Anomala ala rufocuprea), Anomala albopilosa, bean squirrel (Popillia japonica), nagachakogane (Heptophylla picea), European Chafer (Rhizotrogus majalis), black marsh squirrel (Tomarus gibbosus), holotrichia genus, hyllophia lob s abderus genus Diloboderus genus Scarabaeidae; cotton beetle (Araecerus coffeae), aphid weevil (Cylas formicarius), weevil (Euscepes postfasciatus), alfalfa weevil (Hypera post zoe) (Echinocnemus squameus), rice weevil (Lissorhoptrus oryzophilus), white-headed weevil (Rhabdoscelus lineatocollis), cotton weevil (Anthonomus grandis), sword weevil (Sphenophorus venatus), Southern Corn Billbug (Sphenophusweest stalk stalk) , Sugarcane weevil (Sphenophorus levis), Sabigo weevil (Scepticus griseus), Scoticus uniform weevil (Scepticus uniformis), Brazilian weevil (Zabrotes subfasciatus), pine beetle (Tomicus piniperda), Coffee Berry Borer (Hypothenemus hampei), Aracanthus genus such as Aracanthus mourei, culmidae (Curculionidae) such as cotton root borer (Eutinobothrus brasiliensis); Tribolium castaneum, ), Ladybirds such as Epilachna vigintioctopunctata (Coccinellidae); beetles such as Lyctus brunneus (Bostrychidae); Ptinidae; Cerambycidae; Melanotus okinawensis, Agriotes fuscicollis, Melanotus sp., Elousus sp. , Limonius sp., Conoderu s sp., Ctenicera sp.); Staphylinidae, such as Paederus fuscipes.

  Orthoptera: Orthooptera: Locusta migratoria, Moroccan locust (Dociostaurus maroccanus), Australian locust (Chortoicetes terminifera), Red-necked grasshopper (Nomadacris septemfasciata), Brown Locust (Locustana parustina, Locustana pardalina, Locustana pardalina) Italian Locust (Calliptamus italicus), Differential grasshopper (Melanoplus differentialis), Two striped grasshopper (Melanoplus bivittatus), Migratory grasshopper (Melanoplus sanguinipes), Red-Legged grasshopper (Melanoplus femurrubrum), Clearwinged grasshopper (Camnula pellucister) gregaria), Yellow-winged locust (Gastrimargus musicus), Spur-throated locust (Austracris guttulosa), Cobainago (Oxya yezoensis), Scarlet moth (Oxya japonica), Thai winged locust (Patanga succincta), etc. a ricidae (Gryllotalpidae) such as a africana; crickets (Gryllidae) such as European cricket (Acheta domesticus) and Teleogryllus emma; and Tettigoniidae such as Mormon cricket (Anabrus simplex).

  Hymenoptera: Ants such as Athalia rosae and Athalia japonica, Tenthredinidae; Fire ant (Solenopsis spp.), Brown leaf-cutting ant (Atta capiguara) Department (Formicidae) etc.

  Cockroaches (Blattodea): German cockroach (Blattellidae) such as Blattella germanica; Black cockroach (Periplaneta fuliginosa), American cockroach (Periplaneta americana), Greater cockroach (Periplaneta brunnea), Greater cockroach (B) Family (Blattidae); Yamato termite (Reticulitermes speratus), termite (Coptotermes formosanus), American ant termite (Incisitermes minor), scallop termite (Cryptotermes domesticus), taiwan termite (Odontotermes formosanus), hun Nen termis (Glyptotermes satsumensis), long term termite (Glyptotermes nakajimai), long term termite (Glyptotermes fuscus), large termite (Hodotermopsis sjostedti), long term termite (Coptotermes guangzhouensis), amami Loite (Reticulitermes namobei), Miyatake termite (Reticulitermes miyatakei), Japanese termite (Reticulitermes kanmonensis), Takasago termite (Nasutitermes takasagoensis), Ants termites (Pericapritermes nitobei), Shari termites (mu) termites (mu) termites ).

  Acari: Tick spider mites (Tetranychus urticae), Kantawa spider mite (Tetranychus kanzawai), Aedes spp. (Aculops pelekassi), Ryukyu mandarin mite (Phyllocoptruta citri), Tomato rust mite (Aculops lycopersici), Chinese rustic mite (Calacarus carinatus), Chinese prickly tick (Acaphylla theavagrans), Green moss mite (Eriophytchile) Eriophyidae, such as Aceria diospyri, Aceria tosichella, Shevtchenkella sp .; Dustaceae, such as Polyphagotarsonemus latus; Tarsonemidae; Brevipalpus phoenicis, etc. Tenuipalpidae; Tuckerellidae; Haemaphysalis longicornis, Haemaphysalis flava, Dermacentor taiwanensis, Dermacentor tus, Tick Ixodes persulcatus, black legged ticks (Ixodes scapularis), Amblyomma americanum, Boophilus microplus, Rhipicephalus sanguineus, etc. Tick (Ixodidae); Acaridae such as Tyrophagus similis; Dermatophagoides pteronyssinus such as Dermatophagoides farinae; Pyroglyphidae; uditus), Scarlet mite (Cheyletus malaccensis), Scarlet ticks (Cheyletus moorei), Scarlet ticks (Cheyletiella yasguri), etc. (Cheyletidae); Demodexidae, such as Demodex canis; Listrophoridae; Haplochthoniidae; Ornithonyssus bacoti; ), Etc .; Dermanyssidae; Leptotrombidium akamushi, etc.

The composition of the present invention contains the present compound and an inert carrier. The composition of the present invention is usually prepared by mixing the present compound with an inert carrier such as a solid carrier, a liquid carrier, a gaseous carrier, etc., and adding a surfactant or other adjuvant for formulation as necessary. , Oils, powders, granules, wettable powders, flowables, microcapsules, aerosols, smoke agents, poison baits, resin preparations, shampoos, pastes, foams, carbon dioxide preparations, tablets, etc. It becomes. These preparations may be used after being processed into mosquito coils, electric mosquito mats, liquid mosquito traps, fumigants, fumigants, sheet preparations, spot-on agents, or oral treatments. The composition of the present invention can also be mixed with other insecticides, acaricides, nematicides, fungicides, plant growth regulators, herbicides and synergists. For the formulation, the present compound may be used, or the present compound in the form of an acid addition salt.
The composition of the present invention usually contains 0.01 to 95% by weight of the present compound.

  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 powders and granules of chemical fertilizers (ammonium sulfate, phosphorous acid, ammonium nitrate, urea, ammonium chloride, etc.), and synthetic resins (polypropylene, polyacrylonitrile, polymethyl methacrylate) Polyester resins such as polyethylene terephthalate, nylon resins such as nylon-6, nylon-11, and nylon-66, polyamide resins, polyvinyl chloride, polyvinylidene chloride, and vinyl chloride-propylene copolymers).

  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. ), Amides (DMF, dimethylacetamide, etc.), sulfoxides (dimethylsulfoxide (hereinafter referred to as DMSO), etc.), propylene carbonate and vegetable oils (soybean oil, cottonseed oil, etc.).

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

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

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

Examples of the base material of the resin preparation include vinyl chloride polymers, polyurethanes, etc., and these base materials include phthalic acid esters (dimethyl phthalate, dioctyl phthalate, etc.) and adipic acid esters as necessary. Further, a plasticizer such as stearic acid may be added. The resin formulation is obtained by kneading the compound in the base material using a normal kneading apparatus, and then molding by injection molding, extrusion molding, press molding, etc., and if necessary, through steps such as molding, cutting, It can be processed into resin preparations such as plate, film, tape, net, and string. These resin preparations are processed, for example, as animal collars, animal ear tags, sheet preparations, attracting strings, or gardening supports.
Examples of the base material of the poison bait include cereal flour, vegetable oil, sugar, crystalline cellulose and the like, and further, if necessary, preservation of antioxidants such as dibutylhydroxytoluene and nordihydroguaiaretic acid, dehydroacetic acid and the like Ingredients, anti-fouling preventives for children and pets such as pepper powder, cheese flavor, onion flavor, peanut oil and other insect-attracting flavors are added.

  In the method for controlling harmful arthropods of the present invention, an effective amount of the present compound is applied to harmful arthropods and / or to the habitat of harmful arthropods (plants, soil, households, animal bodies, etc.). Is done.

When the composition of the present invention is used for controlling harmful arthropods in the agricultural field, the application amount of the present compound is usually 1 to 10,000 g per 10,000 m ² . When the composition 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 concentration of the compound is 0.01 to 10,000 ppm. Powders are usually applied as they are.

  These preparations and water dilutions of these preparations may be applied directly to harmful arthropods or plants to be protected from harmful arthropods, and to control harmful arthropods that inhabit cultivated soil. In addition, the soil may be treated.

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

When the composition of the present invention is used for controlling harmful arthropods that inhabit a house, the amount of the compound applied is usually 0.01 to 1000 mg per 1 m ² of treatment area when treated on the surface. When processing to space, it is 0.01-500 mg normally per 1 m < ³ > of processing space. When the composition of the present invention is formulated into an emulsion, wettable powder, flowable agent, etc., it is usually diluted with water so that the concentration of the present compound is 0.1 to 10,000 ppm, and is applied as an oil or aerosol. Apply smoke, poisonous bait, etc. as they are.

  When the composition of the present invention is used for controlling ectoparasites of domestic animals for cattle, horses, pigs, sheep, goats, chickens, and other small animals such as dogs, cats, rats, and mice, Can be used for As a specific method of use, for the purpose of systemic suppression, for example, administration by tablet, feed mixing, suppository, injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.) is intended for non-systemic suppression. In this case, for example, an oil agent or an aqueous liquid is sprayed, a pour-on treatment or a spot-on treatment is performed, the animal is washed with a shampoo preparation, or a resin preparation is attached to the animal with a collar or ear tag. The amount of the present compound when administered to an animal body is usually in the range of 0.1 to 1000 mg per 1 kg body weight of the animal.

  Hereinafter, the present invention will be described with reference to production examples, formulation examples, and test examples, but the present invention is not limited to these examples. In the present specification, Me represents a methyl group, Boc represents a tert-butoxycarbonyl group, and Ph represents a phenyl group.

本化合物１：¹Ｈ−ＮＭＲ（ＣＤＣｌ₃、ＴＭＳ、δ（ｐｐｍ））： ７．３２（２Ｈ，ｔ），７．２３（１Ｈ，ｔ），７．１４（２Ｈ，ｄ），６．９４（１Ｈ，ｓ），６．４３（１Ｈ，ｓ），３．９４−３．８３ （２Ｈ，ｍ），３．７７（１Ｈ，ｄｄ），３．５９（１Ｈ，ｄｄ），３．４５（２Ｈ，ｔ），２．６２−２．４７（２Ｈ，ｍ），２．３５−２．３１（１Ｈ，ｍ），２．１２−２．０３（１Ｈ，ｄｔ），１．７１−１．５７（３Ｈ，ｍ）． Production Example 1
Triethylamine 0.17 mL was added to a mixture of tetrahydrofuran-3-ylmethanamine hydrochloride 0.16 g and chloroform 2.5 mL, followed by stirring for 30 minutes. To this mixture was added 0.23 g of 5- (2-phenylcyclopropyl) isoxazole-3-carboxylic acid, 0.014 g of 1-hydroxybenzotriazole, and 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride. 23 g was sequentially added, and the mixture was stirred at room temperature for 3 hours. 1N Hydrochloric acid was added to this mixture, and the mixture was stirred for 30 min and extracted twice with chloroform. The obtained organic layer was filtered through silica gel, and the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.27 g of a compound represented by the following formula (hereinafter referred to as the present compound 1). In addition, this compound 1 is a diastereomeric mixture derived from a cyclopropane ring.

This compound 1: ¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 7.32 (2H, t), 7.23 (1H, t), 7.14 (2H, d), 6.94 (1H, s), 6.43 (1H, s), 3.94-3.83 (2H, m), 3.77 (1H, dd), 3.59 (1H, dd), 3.45 ( 2H, t), 2.62-2.47 (2H, m), 2.35-2.31 (1H, m), 2.12-2.03 (1H, dt), 1.71-1. 57 (3H, m).

で示される化合物において、Ｇ及びＲ¹が［表１］に記載のいずれかで示される化合物。なお、本化合物２、３及び４は、シクロプロパン環に由来にするジアステレオマー混合物である。 Production Example 2
The compounds produced according to the method described in Production Example 1 and their physical properties are shown below.
Formula (IA)

In which G and R ¹ are any one of those described in [Table 1]. In addition, this compound 2, 3 and 4 are diastereomeric mixtures derived from a cyclopropane ring.

［表１の続き］

［表１の続き］

本化合物２：¹Ｈ−ＮＭＲ（ＣＤＣｌ₃、ＴＭＳ、δ（ｐｐｍ））：７．３２（２Ｈ，ｔｔ，），７．２３ （１Ｈ，ｔｔ），７．１４（２Ｈ，ｄｔ，），６．８７（１Ｈ，ｂｒ ｓ），６．４３（１Ｈ，），４．００−３．９７（２Ｈ，ｍ），３．３９−３．３４（４Ｈ，ｍ），２．５１−２．４９（１Ｈ，ｍ），２．３４−２．３２（１Ｈ，ｍ），１．９２−１．８０（１Ｈ，ｍ）， １．６８−１．５７（４Ｈ，ｍ），１．３９−１．３５（２Ｈ，ｍ）．
本化合物３：¹Ｈ−ＮＭＲ（ＣＤＣｌ₃、ＴＭＳ、δ（ｐｐｍ））：８．０８（１Ｈ，ｂｒ ｓ），７．３５−７．３１（２Ｈ，ｍ），７．２６−７．２４（１Ｈ，ｍ），７．１９−７．１１（５Ｈ，ｍ），６．５３ （１Ｈ，ｓ），２．５５−２．５３（１Ｈ，ｍ），２．３８−２．３６（１Ｈ，ｍ），２．２９（６Ｈ，ｓ），１．７２−１．５９（２Ｈ，ｍ）．
本化合物４：¹Ｈ−ＮＭＲ（ＣＤＣｌ₃、ＴＭＳ、δ（ｐｐｍ））：７．３３−７．３０（２Ｈ，ｍ），７．２５−７．２１（１Ｈ，ｍ），７．１５−７．１２（２Ｈ，ｍ），６．８６（１Ｈ，ｂｒｓ），６．４４（１Ｈ，ｓ），３．２６（２Ｈ，ｔ），２．５４−２．４７（１Ｈ，ｍ），２．３６−２．３０（１Ｈ， ｍ），１．９６−１．８２（１Ｈ，ｍ），１．７２−１．５７（２Ｈ，ｍ），０．９８（３Ｈ，ｓ），０．９６（３Ｈ，ｓ）．
本化合物５：¹Ｈ−ＮＭＲ（ＣＤＣｌ₃、ＴＭＳ、δ（ｐｐｍ））：７．３０−７．２３（２Ｈ，ｍ），７．１９（１Ｈ，ｄｔ），７．１１−７．０９（２Ｈ，ｍ），６．９６（１Ｈ，ｂｒ ｓ），６．４５（１Ｈ，ｓ）， ３．９４−３．８４（２Ｈ，ｍ），３．７８−３．７６（１Ｈ，ｍ），３．６０−３．５８（１Ｈ， ｍ），３．４８−３．４４（２Ｈ，ｍ），２．６７−２．５１（３Ｈ，ｍ），２．３１−２．２２（１Ｈ，ｍ），２．１４−２．０５（１Ｈ，ｍ），１．７３−１．５７（２Ｈ，ｍ），１．４２−１．３２（１Ｈ，ｍ），１．０５（１Ｈ，ｑ）．
本化合物６：¹Ｈ−ＮＭＲ（ＣＤＣｌ₃、ＴＭＳ、δ（ｐｐｍ））：７．３３−７．２９（２Ｈ，ｍ），７．２５−７．２０（３Ｈ，ｍ），６．９２（１Ｈ，ｂｒ ｓ），６．３２（１Ｈ，ｓ），３．９３−３．８２（２Ｈ，ｍ），３．７８−３．７２（１Ｈ，ｍ），３．６０−３．５４（１Ｈ，ｍ），３．４９−３．３８（２Ｈ，ｍ），２．８３−２．７０（２Ｈ，ｍ），２．６１−２．４９（１Ｈ，ｍ），２．１２−２．０１（１Ｈ，ｍ），２．００−１．９３（１Ｈ，ｍ），１．７１−１．５９（２Ｈ，ｍ），１．２８−１．２３（１Ｈ，ｍ），１．１３−１．０４（１Ｈ，ｍ）．
本化合物７：¹Ｈ−ＮＭＲ（ＣＤＣｌ₃、ＴＭＳ、δ（ｐｐｍ））：７．３０−７．２３（２Ｈ，ｍ），７．２１−７．１７（１Ｈ，ｍ），７．１１−７．０９（２Ｈ，ｍ），６．９０（１Ｈ，ｂｒ ｓ），６．４４（１Ｈ，ｓ），４．０２−３．９５（２Ｈ，ｍ），３．４３−３．３１（４Ｈ，ｍ），２．６８−２．４９（２Ｈ，ｍ），２．２９−２．２３（１Ｈ，ｍ），１．９３−１．８０（１Ｈ，ｍ），１．７０−１．６０（４Ｈ，ｍ），１．４３−１．３２（３Ｈ，ｍ）．
本化合物８：¹Ｈ−ＮＭＲ（ＣＤＣｌ₃、ＴＭＳ、δ（ｐｐｍ））：７．３３−７．２９（２Ｈ，ｍ），７．２６−７．１９（３Ｈ，ｍ），６．８４（１Ｈ，ｂｒ ｓ），６．３１（１Ｈ，ｓ），４．００−３．９６（２Ｈ，ｍ），３．４２−３．２７（４Ｈ，ｍ），２．８２−２．７０（２Ｈ，ｍ），１．９９−１．９４（１Ｈ，ｍ），１．９０−１．７８（１Ｈ，ｍ），１．６８−１．６１（３Ｈ，ｍ），１．４２−１．２９（２Ｈ，ｍ），１．２８−１．２３（１Ｈ，ｍ），１．１３−１．０５（１Ｈ，ｍ）．
本化合物９：¹Ｈ−ＮＭＲ（ＣＤＣｌ₃、ＴＭＳ、δ（ｐｐｍ））：７．２９−７．２３（２Ｈ，ｍ），７．２１−７．１６（１Ｈ，ｍ），７．１２−７．０７（２Ｈ，ｍ），６．８６（１Ｈ，ｂｒ ｓ），６．４５（１Ｈ，ｓ），３．２７（２Ｈ，ｔ），２．６９−２．４９（３Ｈ，ｍ），２．２９−２．２１（１Ｈ， ｍ），１．９５−１．８３（１Ｈ，ｍ），１．６７−１．５８（１Ｈ，ｍ），１．４２−１．３２（１Ｈ，ｍ），０．９９（３Ｈ，ｓ），０．９７（３Ｈ，ｓ）．
本化合物１０：¹Ｈ−ＮＭＲ（ＣＤＣｌ₃、ＴＭＳ、δ（ｐｐｍ））：７．３３−７．２９（２Ｈ，ｍ），７．２４−７．２１（３Ｈ，ｍ），６．７９（１Ｈ，ｂｒ ｓ），６．３２（１Ｈ，ｓ），３．２４（２Ｈ，ｔ）， ２．８３−２．７０（２Ｈ，ｍ），１．９９−１．９４（１Ｈ，ｍ），１．９０−１．８３（１Ｈ， ｍ），１．６７−１．６２（１Ｈ，ｍ），１．２８−１．２２（１Ｈ，ｍ），１．１２−１．０５（１Ｈ，ｍ），０．９６（３Ｈ，ｓ），０．９５（３Ｈ，ｓ）．
本化合物１１：¹Ｈ−ＮＭＲ（ＣＤＣｌ₃、ＴＭＳ、δ（ｐｐｍ））：８．４８（１Ｈ，ｂｒｓ），８．４２（１Ｈ，ｄ），８．３４（１Ｈ，ｄ），７．３１−７．１７（４Ｈ， ｍ），７．１５−７．０７（２Ｈ，ｍ）， ６．５４（１Ｈ，ｓ），２．７１−２．５５（５Ｈ，ｍ），２．３５−２．２７（１Ｈ，ｍ），１．７４−１．６４（１Ｈ，ｍ），１．４６−１．３８（１Ｈ，ｍ），１．１１（１Ｈ，ｑ）．
本化合物１２：¹Ｈ−ＮＭＲ（ＣＤＣｌ₃、ＴＭＳ、δ（ｐｐｍ））：８．４３（１Ｈ，ｂｒｓ），８．３８（１Ｈ，ｄ），８．３３（１Ｈ，ｄ），７．３６−７．１８（５Ｈ，ｍ），６．４２（１Ｈ，ｓ），４．１２ （１Ｈ，ｑ），２．８５−２．７３（２Ｈ，ｍ），２．５９（３Ｈ，ｓ），２．０４−１．９９（１Ｈ，ｍ），１．７３−１．６６（１Ｈ，ｍ），１．３３−１．２９（１Ｈ，ｍ），１．１８−１．１０（１Ｈ，ｍ）．
本化合物１３：¹Ｈ−ＮＭＲ （ＣＤＣｌ₃、ＴＭＳ、δ（ｐｐｍ））：７．３４−７．２８（２Ｈ，ｍ），７．２６−７．２０（３Ｈ，ｍ），７．０９（１Ｈ，ｂｒ ｓ），６．３２（１Ｈ，ｓ），３．７１−３．６３ （１Ｈ，ｍ），３．５４−３．４５（１Ｈ，ｍ），３．３６（３Ｈ，ｓ），３．２８−３．２１（１Ｈ，ｍ），２．８３−２．７０（２Ｈ，ｍ），１．９９−１．９４（１Ｈ，ｍ），１．７０−１．６１（１Ｈ，ｍ），１．２８−１．２３（１Ｈ，ｍ），１．１７（３Ｈ，ｄ），１．１２−１．０５（１Ｈ，ｍ）．
本化合物１４：¹Ｈ−ＮＭＲ（ＣＤＣｌ₃、ＴＭＳ、δ（ｐｐｍ））：７．４２（１Ｈ，ｂｒｓ），６．３３（１Ｈ，ｓ），３．３２（２Ｈ，ｄ），２．２１（６Ｈ，ｓ），２．１１−２．０４（１Ｈ，ｍ），１．１４−１．０８（２Ｈ，ｍ），１．０４１（６Ｈ，ｓ），１．６５−０．８５（２Ｈ，ｍ）．
本化合物１５：¹Ｈ−ＮＭＲ（ＣＤＣｌ₃、ＴＭＳ、δ（ｐｐｍ））：７．４１（１Ｈ，ｂｓｍ），６ ．３２（１Ｈ，ｓ），３．３２（２Ｈ，ｄ），２．２１（１Ｈ，ｓ），２．１０−２．０４（６Ｈ，ｓ），１．１４−１．０８（２Ｈ，ｍ），１．０４（６Ｈ，ｓ），２．２０−２．０５（２Ｈ，ｍ），１．００−０．９５（２Ｈ，ｍ）．
本化合物１６：¹Ｈ−ＮＭＲ（ＣＤＣｌ₃、ＴＭＳ、δ（ｐｐｍ））：７．２４（１Ｈ，ｂｒｓ），６．３３（１Ｈ，ｓ），３．３０（２Ｈ，ｄ），２．１２−２．０４（１Ｈ，ｍ），１．３５（２Ｈ，ｓ），１．１６（６Ｈ，ｓ）１．１４−１．０８（２Ｈ，ｍ），１．０１−０．９６（２Ｈ，ｍ）．
本化合物１７：¹Ｈ−ＮＭＲ（ＣＤＣｌ₃、ＴＭＳ、δ（ｐｐｍ））：７．１４（１Ｈ，ｂｓｍ），６ ．３２（１Ｈ，ｓ），４．８４−４．７４（１Ｈ，ｍ），４．３０（２Ｈ，ｔ），３．８６（２Ｈ，ｄｄ），２．１２−２．０３（１Ｈ，ｍ），１．４５（９Ｈ，ｓ）１．１７−１．１０（２Ｈ，ｍ），１．０２−０．９６（２Ｈ，ｍ）．
本化合物１８：¹Ｈ−ＮＭＲ（ＣＤＣｌ₃、ＴＭＳ、δ（ｐｐｍ））：６．６４（１Ｈ，ｂｒｓ），６．３２（１Ｈ，ｓ），４．１６−３．９９（３Ｈ，ｍ），２．９０（２Ｈ，ｔ），２．１１−２．０３（１Ｈ，ｍ），２．０１−１．９４（２Ｈ，ｍ），１．５８（２Ｈ，ｍ），１．４６（９Ｈ，ｓ），１．１５−１．０９（２Ｈ，ｍ），１．０１−０．９５（２Ｈ，ｍ）．
本化合物１９：¹Ｈ−ＮＭＲ（ＣＤＣｌ₃、ＴＭＳ、δ（ｐｐｍ））： ６．６４（１Ｈ，ｂｒｓ），６．３２（１Ｈ，ｓ），３．９８−３．８９（１Ｈ，ｍ），２．８０（２Ｈ、ｄ），２．２９（３Ｈ，ｓ），２．１３（２Ｈ，ｔ），２．０９−２．０５（１Ｈ，ｍ），２．００（２Ｈ，ｄｄ），１．６１−１．５３（２Ｈ，ｍ），１．１４−１．０８（２Ｈ，ｍ），１．００−０．９４（２Ｈ，ｍ）．
本化合物２８：¹Ｈ−ＮＭＲ（ＣＤＣｌ₃、ＴＭＳ、δ（ｐｐｍ））：６．６１（１Ｈ，ｓ），６．３２（１Ｈ，ｓ），３．９７−３．８７（１Ｈ，ｍ），２．１１−２．０２（１Ｈ，ｍ），２．０２−１．９５（２Ｈ，ｍ），１．７９−１．７１（２Ｈ，ｍ），１．６９−１．６０（１Ｈ，ｍ），１．４７−１．３３（２Ｈ，ｍ），１．３１−１．１８（３Ｈ，ｍ），１．１３−１．０７（２Ｈ，ｍ），１．００−０．９４（２Ｈ，ｍ）．
本化合物２９：¹Ｈ−ＮＭＲ（ＣＤＣｌ₃、ＴＭＳ、δ（ｐｐｍ））：８．４３（１Ｈ，ｂｒｓ），８．０５−８．００（１Ｈ，ｍ），７．３０−７．２０（２Ｈ，ｍ），７．１５−７．０５（１Ｈ，ｍ），６．５２（１Ｈ，ｓ），３．３２−３．２０（１Ｈ，ｍ），２．３５（３Ｈ，ｓ），２．２０−２．０８（２Ｈ，ｍ），１．８５−１．６５（６Ｈ，ｍ）．
本化合物３０：¹Ｈ−ＮＭＲ（ＣＤＣｌ₃、ＴＭＳ、δ（ｐｐｍ））：８．４７（１Ｈ，ｂｒｓ），７．９０−７．８４（１Ｈ，ｍ），７．３０−７．１５（２Ｈ，ｍ），６．５２（１Ｈ，ｓ），３．３２−３．２２（１Ｈ，ｍ），２．４０（３Ｈ，ｓ），２．２０−２．０５（２Ｈ，ｍ），１．８５−１．６８（６Ｈ，ｍ）．
本化合物３２：¹Ｈ−ＮＭＲ（ＣＤＣｌ₃、ＴＭＳ、δ（ｐｐｍ））：９．１０（１Ｈ，ｂｒｓ），６．４０（１Ｈ，ｓ），３．３６−３．３２（２Ｈ，ｍ），３．２９−３．１７（１Ｈ，ｍ），２．３４（６Ｈ，ｓ），２．３３−２．２８（２Ｈ，ｍ），２．１８−２．０５（２Ｈ，ｍ），１．８２−１．６２（６Ｈ，ｍ），０．９７（６Ｈ，ｓ）．
本化合物３３：¹Ｈ−ＮＭＲ（ＣＤＣｌ₃、ＴＭＳ、δ（ｐｐｍ））：６．９０（１Ｈ，ｂｒｓ），６．４２（１Ｈ，ｓ），３．９５−３．７２（３Ｈ，ｍ），３．６２−３．５２（１Ｈ，ｍ），３．５０−３．４０（２Ｈ，ｍ），３．３０−３．１８（１Ｈ，ｍ），２．６２−２．５１（１Ｈ，ｍ），２．１８−２．０２（３Ｈ，ｍ），１．９２−１．６０（７Ｈ，ｍ）．
本化合物３４：¹Ｈ−ＮＭＲ（ＣＤＣｌ₃、ＴＭＳ、δ（ｐｐｍ））：６．６０（１Ｈ，ｂｒｓ），６．４１（１Ｈ，ｓ），３．９６−３．８６（１Ｈ，ｍ），３．７１−３．６２（１Ｈ，ｍ），３．２９−３．１７（１Ｈ，ｍ），２．１８−２．００（６Ｈ，ｍ），１．８２−１．６５（６Ｈ，ｍ），１．５２−１．３０（５Ｈ，ｍ）．
本化合物３５：¹Ｈ−ＮＭＲ（ＣＤＣｌ₃、ＴＭＳ、δ（ｐｐｍ））：６．６５（１Ｈ，ｂｒｓ），６．４１（１Ｈ，ｓ），４．００−３．９０（１Ｈ，ｍ），３．２８−３．２０（１Ｈ，ｍ），２．８５−２．７２（２Ｈ，ｍ），２．２９（３Ｈ，ｓ），２．２０−１．９５（６Ｈ，ｍ），１．８２−１．５５（８Ｈ，ｍ）．
本化合物３６：¹Ｈ−ＮＭＲ（ＣＤＣｌ₃、ＴＭＳ、δ（ｐｐｍ））：６．６７（１Ｈ，ｂｒｓ），６．４２（１Ｈ，ｄ），４．１５−４．００（３Ｈ，ｍ），３．２８−３．１９（１Ｈ，ｍ），２．９７−２．８４（２Ｈ，ｍ），２．１４−２．０５（２Ｈ，ｍ），２．０３−１．９５（２Ｈ，ｍ），１．６５−１．５８（６Ｈ，ｍ），１．５０−１．３８（１１Ｈ，ｍ）．
本化合物３７：¹Ｈ−ＮＭＲ（ＣＤＣｌ₃、ＴＭＳ、δ（ｐｐｍ））：６．７０（１Ｈ，ｂｒｓ），６．４２（１Ｈ，ｄ），４．０９−３．９８（１Ｈ，ｍ），３．２９−３．１９（１Ｈ，ｍ），３．１５−３．０７（２Ｈ，ｍ），２．７８−２．６９（２Ｈ，ｍ），２．１７−１．９７（４Ｈ，ｍ），１．８３−１．６６（６Ｈ，ｍ），１．４９−１．３７（２Ｈ，ｍ）．
本化合物３８：¹Ｈ−ＮＭＲ（ＣＤＣｌ₃、ＴＭＳ、δ（ｐｐｍ））：８．４４（１Ｈ，ｂｒｓ），８．０５−８．００（１Ｈ，ｍ），７．３０−７．２０（２Ｈ，ｍ），７．１４−７．０８（１Ｈ，ｍ），６．５１（１Ｈ，ｓ），２．９０−２．８２（１Ｈ，ｍ），２．３５（３Ｈ，ｓ），２．１５−２．０５（２Ｈ，ｍ），１．９０−１．８２（２Ｈ，ｍ），１．８０−１．７０（１Ｈ，ｍ），１．５２−１．２６（５Ｈ，ｍ）．
本化合物３９：¹Ｈ−ＮＭＲ（ＣＤＣｌ₃、ＴＭＳ、δ（ｐｐｍ））：８．４７（１Ｈ，ｂｒｓ），７．８９−７．８５（１Ｈ，ｍ），７．３０−７．１５（２Ｈ，ｍ），６．５０（１Ｈ，ｓ），２．９０−２．８２（１Ｈ，ｍ），２．４０（３Ｈ，ｓ），２．１２−２．０４（２Ｈ，ｍ），１．８８−１．８０（２Ｈ，ｍ），１．７８−１．７０（１Ｈ，ｍ），１．５５−１．２５（５Ｈ，ｍ）．
本化合物４１：¹Ｈ−ＮＭＲ（ＣＤＣｌ₃、ＴＭＳ、δ（ｐｐｍ））：９．１０（１Ｈ，ｂｒｓ），６．３９（１Ｈ，ｓ），３．４８−３．４２（２Ｈ，ｍ），２．８８−２．７５（１Ｈ，ｍ），２．３４（６Ｈ，ｓ），２．１２−２．０２（２Ｈ，ｍ），１．９０−１．２０（１０Ｈ，ｍ），０．９７（６Ｈ，ｓ）．
本化合物４２：¹Ｈ−ＮＭＲ（ＣＤＣｌ₃、ＴＭＳ、δ（ｐｐｍ））：６．９１（１Ｈ，ｂｒｓ），６．４１（１Ｈ，ｓ），３．９４−３．８０（２Ｈ，ｍ），３．８９−３．７２（１Ｈ，ｍ），３．６０−３．５５（１Ｈ，ｍ），３．４９−３．４０（２Ｈ，ｍ），２．８５−２．７５（１Ｈ，ｍ），２．６０−２．５２（１Ｈ，ｍ），２．１３−２．０３（３Ｈ，ｍ），１．９０−１．２０（９Ｈ，ｍ）．
本化合物４３：¹Ｈ−ＮＭＲ（ＣＤＣｌ₃、ＴＭＳ、δ（ｐｐｍ））：６．６０（１Ｈ，ｂｒｓ），６．４０（１Ｈ，ｓ），３．９８−３．８８（１Ｈ，ｍ），３．７０−３．６０（１Ｈ，ｍ），２．８５−２．７５（１Ｈ，ｍ），２．１２−１．９８（６Ｈ，ｍ），１．８５−１．２０（１３Ｈ，ｍ）．
本化合物４４：¹Ｈ−ＮＭＲ（ＣＤＣｌ₃、ＴＭＳ、δ（ｐｐｍ））：６．６６（１Ｈ，ｂｒｓ），６．４０（１Ｈ，ｓ），４．００−３．９０（１Ｈ，ｍ），２．９０−２．７５（３Ｈ，ｍ），２．２９（３Ｈ，ｓ），２．２０−１．９８（６Ｈ，ｍ），１．８８−１．２０（１０Ｈ，ｍ）．
本化合物４５：¹Ｈ−ＮＭＲ（ＣＤＣｌ₃、ＴＭＳ、δ（ｐｐｍ））：６．６７（１Ｈ，ｂｒｓ），６．４１（１Ｈ，ｄ），４．１６−４．００（３Ｈ，ｍ），２．９８−２．７６（３Ｈ，ｍ），２．１０−１．９５（４Ｈ，ｍ），１．６９−１．５１（３Ｈ，ｍ），１．４６−１．２０（１６Ｈ，ｍ）．
本化合物４６：¹Ｈ−ＮＭＲ（ＣＤＣｌ₃、ＴＭＳ、δ（ｐｐｍ））：６．７０（１Ｈ，ｂｒｓ），６．４１（１Ｈ，ｄ），４．１０−３．９９（１Ｈ，ｍ），３．１５−３．０７（２Ｈ，ｍ），２．８６−２．６９（３Ｈ，ｍ），２．０９−１．９７（４Ｈ，ｍ），１．８６−１．６８（３Ｈ，ｍ），１．５２−１．２２（７Ｈ，ｍ）．
本化合物４７：¹Ｈ−ＮＭＲ（ＣＤＣｌ₃、ＴＭＳ、δ（ｐｐｍ））：７．３９−７．３５（２Ｈ，ｍ），７．２９−７．２７（１Ｈ，ｍ），７．２６−７．２５（１Ｈ，ｍ），７．０８−６．９９（１Ｈ，ｂｒ），６．３６（１Ｈ，ｓ），４．５７（２Ｈ，ｄ），２．１１−２．０３（１Ｈ，ｍ），１．３１（９Ｈ，ｓ），１．１４−１．０８（２Ｈ，ｍ），１．００−０．９５（２Ｈ，ｍ）．
本化合物４８：¹Ｈ−ＮＭＲ（ＣＤＣｌ₃、ＴＭＳ、δ（ｐｐｍ））：６．９４−６．８６（１Ｈ，ｍ），６．３３（１Ｈ，ｓ），３．９１（１Ｈ，ｔｄ），３．８５（１Ｈ，ｄｄ），３．７６（１Ｈ，ｄｄ），３．５８（１Ｈ，ｄｄ）３．４４（２Ｈ，ｔ），２．６３−２．５０（１Ｈ，ｍ），２．１３−２．０２（２Ｈ，ｍ），１．７１−１．６５（１Ｈ, ｍ），１．１５−１．０９（２Ｈ，ｍ），１．０１−０．９６（２Ｈ，ｍ）．

[Continuation of Table 1]

[Continuation of Table 1]

Compound 2: ¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 7.32 (2H, tt,), 7.23 (1H, tt), 7.14 (2H, dt,), 6 .87 (1H, brs), 6.43 (1H,), 4.00-3.97 (2H, m), 3.39-3.34 (4H, m), 2.51-2.49 (1H, m), 2.34-2.32 (1H, m), 1.92-1.80 (1H, m), 1.68-1.57 (4H, m), 1.39-1 .35 (2H, m).
Compound 3: ¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 8.08 (1H, brs), 7.35-7.31 (2H, m), 7.26-7.24 (1H, m), 7.19-7.11 (5H, m), 6.53 (1H, s), 2.55-2.53 (1H, m), 2.38-2.36 (1H M), 2.29 (6H, s), 1.7-1.59 (2H, m).
Compound 4: ¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 7.33-7.30 (2H, m), 7.25-7.21 (1H, m), 7.15- 7.12 (2H, m), 6.86 (1H, brs), 6.44 (1H, s), 3.26 (2H, t), 2.54-2.47 (1H, m), 2 .36-2.30 (1H, m), 1.96-1.82 (1H, m), 1.72-1.57 (2H, m), 0.98 (3H, s), 0.96 (3H, s).
Compound 5: ¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 7.30-7.23 (2H, m), 7.19 (1H, dt), 7.11-7.09 ( 2H, m), 6.96 (1H, brs), 6.45 (1H, s), 3.94-3.84 (2H, m), 3.78-3.76 (1H, m), 3.60-3.58 (1H, m), 3.48-3.44 (2H, m), 2.67-2.51 (3H, m), 2.31-2.22 (1H, m ), 2.14-2.05 (1H, m), 1.73-1.57 (2H, m), 1.42-1.32 (1H, m), 1.05 (1H, q).
Compound 6: ¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 7.33-7.29 (2H, m), 7.25-7.20 (3H, m), 6.92 ( 1H, br s), 6.32 (1H, s), 3.93-3.82 (2H, m), 3.78-3.72 (1H, m), 3.60-3.54 (1H M), 3.49-3.38 (2H, m), 2.83-2.70 (2H, m), 2.61-2.49 (1H, m), 2.12-2.01. (1H, m), 2.00-1.93 (1H, m), 1.71-1.59 (2H, m), 1.28-1.23 (1H, m), 1.13-1 .04 (1H, m).
Compound 7: ¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 7.30-7.23 (2H, m), 7.21-7.17 (1H, m), 7.11- 7.09 (2H, m), 6.90 (1H, br s), 6.44 (1H, s), 4.02-3.95 (2H, m), 3.43-3.31 (4H M), 2.68-2.49 (2H, m), 2.29-2.23 (1H, m), 1.93-1.80 (1H, m), 1.70-1.60. (4H, m), 1.43-1.32 (3H, m).
Compound 8: ¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 7.33-7.29 (2H, m), 7.26-7.19 (3H, m), 6.84 ( 1H, br s), 6.31 (1H, s), 4.00-3.96 (2H, m), 3.42-3.27 (4H, m), 2.82-2.70 (2H M), 1.99-1.94 (1H, m), 1.90-1.78 (1H, m), 1.68-1.61 (3H, m), 1.42-1.29. (2H, m), 1.28-1.23 (1H, m), 1.13-1.05 (1H, m).
Compound 9: ¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 7.29-7.23 (2H, m), 7.21-7.16 (1H, m), 7.12- 7.07 (2H, m), 6.86 (1H, br s), 6.45 (1H, s), 3.27 (2H, t), 2.69-2.49 (3H, m), 2.29-2.21 (1H, m), 1.95-1.83 (1H, m), 1.67-1.58 (1H, m), 1.42-1.32 (1H, m ), 0.99 (3H, s), 0.97 (3H, s).
Compound 10: ¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 7.33-7.29 (2H, m), 7.24-7.21 (3H, m), 6.79 ( 1H, br s), 6.32 (1H, s), 3.24 (2H, t), 2.83-2.70 (2H, m), 1.99-1.94 (1H, m), 1.90-1.83 (1H, m), 1.67-1.62 (1H, m), 1.28-1.22 (1H, m), 1.12-1.05 (1 H, m) ), 0.96 (3H, s), 0.95 (3H, s).
Compound 11: ¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 8.48 (1H, brs), 8.42 (1H, d), 8.34 (1H, d), 7.31 -7.17 (4H, m), 7.15-7.07 (2H, m), 6.54 (1H, s), 2.71-2.55 (5H, m), 2.35-2 .27 (1H, m), 1.74-1.64 (1H, m), 1.46-1.38 (1H, m), 1.11 (1H, q).
Compound 12: ¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 8.43 (1H, brs), 8.38 (1H, d), 8.33 (1H, d), 7.36 -7.18 (5H, m), 6.42 (1H, s), 4.12 (1H, q), 2.85-2.73 (2H, m), 2.59 (3H, s), 2.04-1.99 (1H, m), 1.73-1.66 (1H, m), 1.33-1.29 (1H, m), 1.18-1.10 (1H, m ).
Compound 13: ¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 7.34-7.28 (2H, m), 7.26-7.20 (3H, m), 7.09 ( 1H, br s), 6.32 (1H, s), 3.71-3.63 (1H, m), 3.54-3.45 (1H, m), 3.36 (3H, s), 3.28-3.21 (1H, m), 2.83-2.70 (2H, m), 1.99-1.94 (1H, m), 1.70-1.61 (1H, m ), 1.28-1.23 (1H, m), 1.17 (3H, d), 1.12-1.05 (1H, m).
Compound 14: ¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 7.42 (1H, brs), 6.33 (1H, s), 3.32 (2H, d), 2.21 (6H, s), 2.11 to 2.04 (1H, m), 1.14 to 1.08 (2H, m), 1.041 (6H, s), 1.65 to 0.85 (2H) , M).
Compound 15: ¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 7.41 (1H, bsm), 6. 32 (1H, s), 3.32 (2H, d), 2.21 (1H, s), 2.10-2.04 (6H, s), 1.14-1.08 (2H, m) , 1.04 (6H, s), 2.20-2.05 (2H, m), 1.00-0.95 (2H, m).
Compound 16: ¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 7.24 (1H, brs), 6.33 (1H, s), 3.30 (2H, d), 2.12 -2.04 (1H, m), 1.35 (2H, s), 1.16 (6H, s) 1.14-1.08 (2H, m), 1.01-0.96 (2H, m).
Compound 17: ¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 7.14 (1H, bsm), 6. 32 (1H, s), 4.84-4.74 (1H, m), 4.30 (2H, t), 3.86 (2H, dd), 2.12 to 2.03 (1H, m) , 1.45 (9H, s) 1.17-1.10 (2H, m), 1.02-0.96 (2H, m).
Compound 18: ¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 6.64 (1H, brs), 6.32 (1H, s), 4.16-3.99 (3H, m) , 2.90 (2H, t), 2.11-1.03 (1H, m), 2.01-1.94 (2H, m), 1.58 (2H, m), 1.46 (9H) , S), 1.15-1.09 (2H, m), 1.01-0.95 (2H, m).
Compound 19: ¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 6.64 (1H, brs), 6.32 (1H, s), 3.98-3.89 (1H, m) , 2.80 (2H, d), 2.29 (3H, s), 2.13 (2H, t), 2.09-2.05 (1H, m), 2.00 (2H, dd), 1.61-1.53 (2H, m), 1.14-1.08 (2H, m), 1.00-0.94 (2H, m).
Compound 28: ¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 6.61 (1H, s), 6.32 (1H, s), 3.97-3.87 (1H, m) , 2.11-2.02 (1H, m), 2.02-1.95 (2H, m), 1.79-1.71 (2H, m), 1.69-1.60 (1H, m), 1.47-1.33 (2H, m), 1.31-1.18 (3H, m), 1.13-1.07 (2H, m), 1.00-0.94 ( 2H, m).
Compound 29: ¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 8.43 (1H, brs), 8.05-8.00 (1H, m), 7.30-7.20 ( 2H, m), 7.15-7.05 (1H, m), 6.52 (1H, s), 3.32-3.20 (1H, m), 2.35 (3H, s), 2 20-2.08 (2H, m), 1.85-1.65 (6H, m).
Compound 30: ¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 8.47 (1H, brs), 7.90-7.84 (1H, m), 7.30-7.15 ( 2H, m), 6.52 (1H, s), 3.32-3.22 (1H, m), 2.40 (3H, s), 2.20-2.05 (2H, m), 1 .85-1.68 (6H, m).
Compound 32: ¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 9.10 (1H, brs), 6.40 (1H, s), 3.36-3.32 (2H, m) , 3.29-3.17 (1H, m), 2.34 (6H, s), 2.33-2.28 (2H, m), 2.18-2.05 (2H, m), 1 .82-1.62 (6H, m), 0.97 (6H, s).
Compound 33: ¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 6.90 (1H, brs), 6.42 (1H, s), 3.95-3.72 (3H, m) , 3.62-3.52 (1H, m), 3.50-3.40 (2H, m), 3.30-3.18 (1H, m), 2.62-2.51 (1H, m), 2.18-2.02 (3H, m), 1.92-1.60 (7H, m).
Compound 34: ¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 6.60 (1H, brs), 6.41 (1H, s), 3.96-3.86 (1H, m) 3.71-3.62 (1H, m), 3.29-3.17 (1H, m), 2.18-2.00 (6H, m), 1.82-1.65 (6H, m), 1.52-1.30 (5H, m).
Compound 35: ¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 6.65 (1H, brs), 6.41 (1H, s), 4.00-3.90 (1H, m) , 3.28-3.20 (1H, m), 2.85-2.72 (2H, m), 2.29 (3H, s), 2.20-1.95 (6H, m), 1 .82-1.55 (8H, m).
Compound 36: ¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 6.67 (1H, brs), 6.42 (1H, d), 4.15-4.00 (3H, m) 3.28-3.19 (1H, m), 2.97-2.84 (2H, m), 2.14 to 2.05 (2H, m), 2.03-1.95 (2H, m), 1.65 to 1.58 (6H, m), 1.50 to 1.38 (11H, m).
Compound 37: ¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 6.70 (1H, brs), 6.42 (1H, d), 4.09-3.98 (1H, m) , 3.29-3.19 (1H, m), 3.15-3.07 (2H, m), 2.78-2.69 (2H, m), 2.17-1.97 (4H, m), 1.83-1.66 (6H, m), 1.49-1.37 (2H, m).
Compound 38: ¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 8.44 (1H, brs), 8.05-8.00 (1H, m), 7.30-7.20 ( 2H, m), 7.14-7.08 (1H, m), 6.51 (1H, s), 2.90-2.82 (1H, m), 2.35 (3H, s), 2 .15-2.05 (2H, m), 1.90-1.82 (2H, m), 1.80-1.70 (1H, m), 1.52-1.26 (5H, m) .
Compound 39: ¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 8.47 (1H, brs), 7.89-7.85 (1H, m), 7.30-7.15 ( 2H, m), 6.50 (1H, s), 2.90-2.82 (1H, m), 2.40 (3H, s), 2.12 to 2.04 (2H, m), 1 .88-1.80 (2H, m), 1.78-1.70 (1H, m), 1.55-1.25 (5H, m).
Compound 41: ¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 9.10 (1H, brs), 6.39 (1H, s), 3.48-3.42 (2H, m) 2.88-2.75 (1H, m), 2.34 (6H, s), 2.12-2.02 (2H, m), 1.90-1.20 (10H, m), 0 97 (6H, s).
Compound 42: ¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 6.91 (1H, brs), 6.41 (1H, s), 3.94-3.80 (2H, m) 3.89-3.72 (1H, m), 3.60-3.55 (1H, m), 3.49-3.40 (2H, m), 2.85-2.75 (1H, m), 2.60-2.52 (1H, m), 2.13-2.03 (3H, m), 1.90-1.20 (9H, m).
Compound 43: ¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 6.60 (1H, brs), 6.40 (1H, s), 3.98-3.88 (1H, m) , 3.70-3.60 (1H, m), 2.85-2.75 (1H, m), 2.12-1.98 (6H, m), 1.85-1.20 (13H, m).
Compound 44: ¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 6.66 (1H, brs), 6.40 (1H, s), 4.00-3.90 (1H, m) , 2.90-2.75 (3H, m), 2.29 (3H, s), 2.20-1.98 (6H, m), 1.88-1.20 (10H, m).
Compound 45: ¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 6.67 (1H, brs), 6.41 (1H, d), 4.16-4.00 (3H, m) 2.98-2.76 (3H, m), 2.10-1.95 (4H, m), 1.69-1.51 (3H, m), 1.46-1.20 (16H, m).
Compound 46: ¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 6.70 (1H, brs), 6.41 (1H, d), 4.10-3.99 (1H, m) 3.15-3.07 (2H, m), 2.86-2.69 (3H, m), 2.09-1.97 (4H, m), 1.86-1.68 (3H, m), 1.52-1.22 (7H, m).
Compound 47: ¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 7.39-7.35 (2H, m), 7.29-7.27 (1H, m), 7.26- 7.25 (1H, m), 7.08-6.99 (1H, br), 6.36 (1H, s), 4.57 (2H, d), 2.11-2.03 (1H, m), 1.31 (9H, s), 1.14-1.08 (2H, m), 1.00-0.95 (2H, m).
Compound 48: ¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 6.94-6.86 (1H, m), 6.33 (1H, s), 3.91 (1H, td) , 3.85 (1H, dd), 3.76 (1H, dd), 3.58 (1H, dd) 3.44 (2H, t), 2.63-2.50 (1H, m), 2 .13-2.02 (2H, m), 1.71-1.65 (1H, m), 1.15-1.09 (2H, m), 1.01-0.96 (2H, m) .

本化合物２０：¹Ｈ−ＮＭＲ（ＣＤＣｌ₃、ＴＭＳ、δ（ｐｐｍ））：９．２０（１Ｈ、ｄ），６．３５（１Ｈ，ｂｒｓ），５．１３−５．０２（１Ｈ，ｍ），４．４１−４．２８（４Ｈ，ｍ），２．９３−２．４８（２Ｈ，ｂｒｓ），２．１１―２．０４（１Ｈ，ｍ），１．１５−１．１０（２Ｈ，ｍ），１．００−０．９５（２Ｈ，ｍ）． Production Example 3
0.60 g of the present compound 17 was added to 5 mL of methanol. To this mixture, 2 mL of a 5-10% hydrogen chloride methanol solution was added under ice cooling, and the mixture was stirred at room temperature for 20.5 hours. To this mixture, 4 mL of a 5-10% hydrogen chloride methanol solution was added under ice cooling, and the mixture was stirred at room temperature for 22 hours. The resulting mixture was concentrated under reduced pressure, and the resulting solid was washed with n-hexane. The obtained solid was filtered and dried to obtain 0.38 g of a compound represented by the following formula (hereinafter referred to as the present compound 20).

Compound 20: ¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 9.20 (1H, d), 6.35 (1H, brs), 5.13-5.02 (1H, m) 4.41-4.28 (4H, m), 2.93-2.48 (2H, brs), 2.11-2.04 (1H, m), 1.15-1.10 (2H, m), 1.00-0.95 (2H, m).

で示される化合物において、Ｒ¹が［表２］に記載のいずれかで示される化合物。 Production Example 4
The compounds produced according to the method described in Production Example 3 and their physical properties are shown below.
Formula (IB)

Wherein R ¹ is any one of those described in [Table 2].

本化合物２１：¹Ｈ−ＮＭＲ（ＤＭＳＯ、ＴＭＳ、δ（ｐｐｍ））：８．８４（１Ｈ，ｄ），６．５１（１Ｈ，ｓ），４．０９−３．９７（１Ｈ，ｍ）３．２８（２Ｈ，ｄ），２．９８（２Ｈ，ｔ），２．２２−２．１５（１Ｈ，ｍ），１，９２（２Ｈ，ｄｄ），１．８４−１．７０（２Ｈ，ｍ），１．１３−１．０７（２Ｈ，ｍ），０．９５−０．８９（２Ｈ，ｍ）．
本化合物２２：¹Ｈ−ＮＭＲ（ＣＤＣｌ₃、ＴＭＳ、δ（ｐｐｍ））：９．１１（１Ｈ，ｂｒｓ），８．８０（１Ｈ，ｂｒｓ），８．２５（１Ｈ，ｂｒｓ），６．３９（１Ｈ，ｓ），５．０４−４．９１（１Ｈ，ｍ），４．６５−４．５６（２Ｈ，ｍ），４．４８−４．３８（２Ｈ，ｍ），２．１４−２．０５（１Ｈ，ｍ），１．１９−１．１２（２Ｈ，ｍ），１．０４−０．９７（２Ｈ，ｍ）．
本化合物２３：¹Ｈ−ＮＭＲ（ＣＤＣｌ₃、ＴＭＳ、δ（ｐｐｍ））：６．３３（１Ｈ，ｓ），４．９５（３Ｈ，ｂｒｓ），４．２３−４．１８（１Ｈ，ｍ），３．５２（２Ｈ，ｄ），３．０６（２Ｈ，ｔ），２．２３（２Ｈ，ｄ），２．１２−２．０４（１Ｈ，ｍ），２．０１−１．８７（２Ｈ，ｍ），１．１７−１．０９（２Ｈ，ｍ），１．０３−０．９４（２Ｈ，ｍ）．

Compound 21: ¹ H-NMR (DMSO, TMS, δ (ppm)): 8.84 (1H, d), 6.51 (1H, s), 4.09-3.97 (1H, m) 3 .28 (2H, d), 2.98 (2H, t), 2.22-2.15 (1H, m), 1,92 (2H, dd), 1.84-1.70 (2H, m) ), 1.13-1.07 (2H, m), 0.95-0.89 (2H, m).
Compound 22: ¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 9.11 (1H, brs), 8.80 (1H, brs), 8.25 (1H, brs), 6.39 (1H, s), 5.04-4.91 (1H, m), 4.65-4.56 (2H, m), 4.48-4.38 (2H, m), 2.14-2 .05 (1H, m), 1.19-1.12 (2H, m), 1.04-0.97 (2H, m).
Compound 23: ¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 6.33 (1H, s), 4.95 (3H, brs), 4.23-4.18 (1H, m) , 3.52 (2H, d), 3.06 (2H, t), 2.23 (2H, d), 2.12-2.04 (1H, m), 2.01-1.87 (2H) , M), 1.17-1.09 (2H, m), 1.03-0.94 (2H, m).

本化合物２４：¹Ｈ−ＮＭＲ（ＣＤＣｌ₃、ＴＭＳ、δ（ｐｐｍ））：６．６６（１Ｈ、ｂｒｓ），６．３２（１Ｈ，ｓ），４．０８−３．９７（１Ｈ，ｍ），３．１０（２Ｈ，ｄｔ），２．７３（２Ｈ，ｄｔ），２．０７（１Ｈ，ｔｔ），２．０３−１．９６（２Ｈ，ｍ），１．４２（２Ｈ，ｄｄｄ），１．１４−１．０８（２Ｈ，ｍ），１．００−０．９５（２Ｈ，ｍ）． Production Example 5
To a mixture of 0.30 g of the present compound 23 and chloroform 3 mL, 0.3 mL of a 0.37 M aqueous potassium carbonate solution was added. The mixture was stirred at room temperature for 18.5 hours, and 2 mL of a 0.37 M aqueous potassium carbonate solution was further added. The mixture was stirred at room temperature for 2 hours. This mixture was extracted with chloroform, and the obtained organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 0.13 g of a compound represented by the following formula (hereinafter referred to as the present compound 24).

Compound 24: ¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 6.66 (1H, brs), 6.32 (1H, s), 4.08-3.97 (1H, m) 3.10 (2H, dt), 2.73 (2H, dt), 2.07 (1H, tt), 2.03-1.96 (2H, m), 1.42 (2H, ddd), 1.14-1.08 (2H, m), 1.00-0.95 (2H, m).

本化合物２７：¹Ｈ−ＮＭＲ（ＤＭＳＯ、ＴＭＳ、δ（ｐｐｍ））：９．３３（１Ｈ，ｄ），６．５１（１Ｈ，ｓ），４．６７−４．５８（１Ｈ，ｍ）,４．３７（１Ｈ,ｔ）,４．１４−４．００（３Ｈ, ｍ），３．８４（１Ｈ，ｄｄ），２．２４−２．１５（１Ｈ，ｍ），１．１３−１．０７（２Ｈ，ｍ），０．９６−０．９０（２Ｈ，ｍ）． Production Example 6
Instead of this compound 23, this compound 22 was used, and 0.08 g of a compound represented by the following formula (hereinafter referred to as this compound 27) was obtained according to the method described in Production Example 5.

Compound 27: ¹ H-NMR (DMSO, TMS, δ (ppm)): 9.33 (1H, d), 6.51 (1H, s), 4.67-4.58 (1H, m), 4.37 (1H, t), 4.14-4.00 (3H, m), 3.84 (1H, dd), 2.24-2.15 (1H, m), 1.13-1. 07 (2H, m), 0.96-0.90 (2H, m).

本化合物２５：¹Ｈ−ＮＭＲ（ＣＤＣｌ₃、ＴＭＳ、δ（ｐｐｍ））：７．０４（１Ｈ、ｂｒｓ），６．３１（１Ｈ，ｓ），４．６５（１Ｈ，ｄｔ），３．６８（２Ｈ，ｄｄ），２．９７（２Ｈ，ｔ），２．３４−２．２８（１Ｈ，ｍ），２．１１−２．０３（１Ｈ，ｍ），１．１５−１．０９（２Ｈ，ｍ），１．０１−０．９６（２Ｈ，ｍ），０．９５（３Ｈ，ｓ），０．９４（３Ｈ，ｓ）． Production Example 7
To a mixture of 0.24 g of the present compound 20 and 3 mL of DMF, 0.05 g of sodium hydride was added under ice cooling, and the mixture was stirred at room temperature for 15 minutes. To this mixture, 0.12 mL of isopropyl iodide was added under ice cooling, and the mixture was stirred at room temperature for 18.5 hours. To this mixture was added a saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (chloroform: methanol = 10: 1) to obtain 0.05 g of a compound represented by the following formula (hereinafter referred to as the present compound 25).

Compound 25: ¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 7.04 (1H, brs), 6.31 (1H, s), 4.65 (1H, dt), 3.68 (2H, dd), 2.97 (2H, t), 2.34-2.28 (1H, m), 2.11-2.03 (1H, m), 1.15-1.09 (2H , M), 1.01-0.96 (2H, m), 0.95 (3H, s), 0.94 (3H, s).

本化合物２６：¹Ｈ−ＮＭＲ（ＣＤＣｌ₃、ＴＭＳ、δ（ｐｐｍ））：７．２９（１Ｈ，ｂｒｓ），６．３２（１Ｈ，ｄ），４．７５−４．６４（１Ｈ，ｍ），３．９２（２Ｈ，ｔ），３．４４（２Ｈ，ｔ），２．５５（３Ｈ，ｓ），２．１３−２．０２（１Ｈ，ｍ），１．１７−１．０９（２Ｈ，ｍ），１．０２−０．９６（２Ｈ，ｍ）． Production Example 8
To a mixture of 0.25 g of the present compound 20 and 10 mL of methanol, 0.86 mL of acetic acid and 0.04 g of 37% formaldehyde aqueous solution were sequentially added, and stirred at room temperature for 1 hour. To this mixture was added 0.14 g of sodium cyanoborohydride, and the mixture was stirred at room temperature for 14 hours. To this mixture, 0.15 g of 37% aqueous formaldehyde solution and 0.15 g of sodium cyanoborohydride were sequentially added and stirred at room temperature for 1.5 hours. The mixture was poured into 10 mL of water and concentrated under reduced pressure. The obtained residue was extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (chloroform: methanol = 10: 1) to obtain 0.03 g of a compound represented by the following formula (hereinafter referred to as the present compound 26).

Compound 26: ¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 7.29 (1H, brs), 6.32 (1H, d), 4.75-4.64 (1H, m) , 3.92 (2H, t), 3.44 (2H, t), 2.55 (3H, s), 2.13-2.02 (1H, m), 1.17-1.09 (2H , M), 1.02-0.96 (2H, m).

中間体１Ａ：¹Ｈ−ＮＭＲ（ＣＤＣｌ_3、ＴＭＳ、δ（ｐｐｍ））：７．３１−７．２６（２Ｈ，ｍ），７．２６−７．１４（３Ｈ，ｍ），３．６２（３Ｈ，ｓ），３．１８（３Ｈ，ｓ），２．８１−２．５９（２Ｈ，ｍ）， １．７２−１．６７（１Ｈ，ｍ），１．３２−１．２６（１Ｈ，ｍ），１．０７−１．０１（１Ｈ， ｍ），０．８６−０．７９（１Ｈ，ｍ）． Reference production example 1
To a mixture of 2.87 g of ethyl 2-benzylcyclopropane-1-carboxylate and 50 mL of THF, 2.05 g of N, O-dimethylhydroxylamine hydrochloride was added. To this mixture, 21.1 mL of a 2M isopropylmagnesium chloride THF solution was added dropwise at −10 ° C. over 15 minutes, followed by stirring at −10 ° C. for 2 hours. After the temperature of the mixture was raised to room temperature, 1N hydrochloric acid was added to the obtained mixture little by little at room temperature. Water was added to this mixture, and the mixture was extracted with t-butyl methyl ether. The obtained organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and a compound represented by the following formula (hereinafter referred to as intermediate 1A) 3 .31 g was obtained. Intermediate 1A is a diastereomeric mixture derived from a cyclopropane ring.

Intermediate 1A: ¹ H-NMR (CDCl _3, TMS, δ (ppm)): 7.31-7.26 (2H, m), 7.26-7.14 (3H, m), 3.62 ( 3H, s), 3.18 (3H, s), 2.81-2.59 (2H, m), 1.72-1.67 (1H, m), 1.32-1.26 (1H, m), 1.07-1.01 (1H, m), 0.86-0.79 (1H, m).

中間体２Ａ：¹Ｈ−ＮＭＲ（ＣＤＣｌ_3、ＴＭＳ、δ（ｐｐｍ））：７．３１−７．２５（２Ｈ，ｍ），７．２０−７．１６（３Ｈ，ｍ），２．９２−２．６２（２Ｈ，ｍ），２．２１（３Ｈ，ｓ），２．１７−２．０９ （１Ｈ，ｍ），１．７１−１．６４（１Ｈ，ｍ），１．３２−１．２４（１Ｈ，ｍ），１．１１−１．０４（１Ｈ，ｍ）．

中間体２Ｂ：¹Ｈ−ＮＭＲ （ＣＤＣｌ_3、ＴＭＳ、δ（ｐｐｍ））：７．３３−７．２７（２Ｈ，ｍ），７．２４−７．１９（３Ｈ， ｍ），２．７４−２．６１（２Ｈ，ｍ），２．２０（３Ｈ，ｓ），１．８７−１．８３（１Ｈ，ｍ），１．７５−１．６６（１Ｈ，ｍ），１．３５−１．３１（１Ｈ ｍ），０．９３−０．８５（１Ｈ，ｍ）． Reference production example 2
To a mixture of 3.29 g of intermediate 1A and 70 mL of THF, 7.0 mL of 3M methylmagnesium bromide diethyl ether solution was added dropwise at 0 ° C. over 1 hour, and the mixture was stirred at 0 ° C. for 2 hours. After the temperature of the mixture was raised to room temperature, 1N hydrochloric acid was added to the obtained mixture little by little at room temperature. Water was added to this mixture, and the mixture was extracted with t-butyl methyl ether. The obtained organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 0.84 g of a cis isomer (hereinafter referred to as Intermediate 2A) represented by the following formula and 1.35 g of a trans isomer (hereinafter referred to as Intermediate 2B). It was.

Intermediate 2A: ¹ H-NMR (CDCl _3, TMS, δ (ppm)): 7.31-7.25 (2H, m), 7.20-7.16 (3H, m), 2.92- 2.62 (2H, m), 2.21 (3H, s), 2.17-2.09 (1H, m), 1.71-1.64 (1H, m), 1.32-1. 24 (1H, m), 1.11-1.04 (1H, m).

Intermediate 2B: ¹ H-NMR (CDCl _3, TMS, δ (ppm)): 7.33-7.27 (2H, m), 7.24-7.19 (3H, m), 2.74- 2.61 (2H, m), 2.20 (3H, s), 1.87-1.83 (1H, m), 1.75-1.66 (1H, m), 1.35-1. 31 (1H m), 0.93-0.85 (1H, m).

中間体３Ａ：¹Ｈ−ＮＭＲ（ＣＤＣｌ_3、ＴＭＳ、δ（ｐｐｍ））：７．３２−７．２８（２Ｈ，ｍ），７．２５−７．２０（１Ｈ，ｍ），７．１４−７．０９（２Ｈ，ｍ），６．５２（１Ｈ，ｓ），４．３５（２Ｈ，ｑ）， ２．７４−２．６７（１Ｈ，ｍ），２．１７−２．１１（１Ｈ，ｍ），１．９０−１．８５（１Ｈ， ｍ），１．６１−１．５５（１Ｈ，ｍ），１．３８（３Ｈ，ｔ）． Reference production example 3
To a mixture of 3.2 g of 1- (2-phenylcyclopropyl) ethane-1-one and 32 mL of ethanol, 3.3 mL of diethyl oxalate was added at −10 ° C. and stirred for 15 minutes. To this mixture, a solution of 6.8 g of 20% sodium ethoxide ethanol solution and 8 mL of ethanol was added dropwise at −10 ° C. over 1 hour and a half, and then stirred at room temperature overnight. The mixture was concentrated under reduced pressure, 1N hydrochloric acid was added to the residue, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 4.42 g of intermediate 3A represented by the following formula. Intermediate 3A is a diastereomeric mixture derived from a cyclopropane ring.

Intermediate 3A: ¹ H-NMR (CDCl _3, TMS, δ (ppm)): 7.32-7.28 (2H, m), 7.25-7.20 (1H, m), 7.14- 7.09 (2H, m), 6.52 (1H, s), 4.35 (2H, q), 2.74-2.67 (1H, m), 2.17-2.11 (1H, m), 1.90-1.85 (1H, m), 1.61-1.55 (1H, m), 1.38 (3H, t).

で示される化合物において、Ｇが［表３］に記載のいずれかである化合物。 Reference production example 4
The compounds produced according to the method described in Reference Production Example 3 and their physical properties are shown below.
Formula (III-A)

In which G is any of those described in [Table 3].

中間体４Ａ：¹Ｈ−ＮＭＲ（ＣＤＣｌ_3、ＴＭＳ、δ（ｐｐｍ））：７．３０−７．２４（２Ｈ，ｍ），７．２０−７．１３（３Ｈ，ｍ），６．５２（１Ｈ，ｓ），４．３５（２Ｈ，ｑ），２．９５−２．７０（２Ｈ，ｍ）， ２．１１−２．０５（１Ｈ，ｍ），１．８８−１．７７（１Ｈ，ｍ），１．４８−１．４４（１Ｈ，ｍ）， １．３７（３Ｈ，ｔ），１．３１−１．２４（１Ｈ，ｍ）．
中間体４Ｂ：¹Ｈ−ＮＭＲ（ＣＤＣｌ_3、ＴＭＳ、δ（ｐｐｍ））：７．３３−７．２９（２Ｈ，ｍ），７．２５−７．１９（３Ｈ，ｍ），６．４５（１Ｈ，ｓ），４．３５（２Ｈ，ｑ），２．７９−２．６８（２Ｈ，ｍ）， １．９４−１．８７（１Ｈ，ｍ），１．８２−１．７７（１Ｈ，ｍ），１．５３−１．４９（１Ｈ， ｍ），１．３７（３Ｈ，ｔ），１．１２−１．０５（１Ｈ，ｍ）．

Intermediate 4A: ¹ H-NMR (CDCl _3, TMS, δ (ppm)): 7.30-7.24 (2H, m), 7.20-7.13 (3H, m), 6.52 ( 1H, s), 4.35 (2H, q), 2.95-2.70 (2H, m), 2.11-1.05 (1H, m), 1.88-1.77 (1H, m), 1.48-1.44 (1H, m), 1.37 (3H, t), 1.31-1.24 (1H, m).
Intermediate 4B: ¹ H-NMR (CDCl _3, TMS, δ (ppm)): 7.33-7.29 (2H, m), 7.25-7.19 (3H, m), 6.45 ( 1H, s), 4.35 (2H, q), 2.79-2.68 (2H, m), 1.94-1.87 (1H, m), 1.82-1.77 (1H, m), 1.53-1.49 (1H, m), 1.37 (3H, t), 1.12-1.05 (1H, m).

中間体５Ａ：¹Ｈ−ＮＭＲ（ＣＤＣｌ_3、ＴＭＳ、δ（ｐｐｍ））：７．３５−７．２８（２Ｈ，ｍ），７．２５−７．２１（１Ｈ，ｍ），７．１６−７．１２（２Ｈ，ｍ），６．４０（１Ｈ，ｓ），４．４３（２Ｈ，ｑ）， ２．５６−２．４９（１Ｈ，ｍ），２．３７−２．３０（１Ｈ，ｍ），１．７２−１．６５（１Ｈ， ｍ），１．６４−１．５６（１Ｈ，ｍ），１．４１（３Ｈ，ｔ）． Reference production example 5
To a mixture of 4.4 g of Intermediate 3A and 56 mL of ethanol, 3.5 g of hydroxylamine hydrochloride was added at room temperature and refluxed for 5 hours under a nitrogen atmosphere. The mixture was cooled to room temperature, water and 1N hydrochloric acid were added, and the mixture was concentrated under reduced pressure. The obtained residue was extracted with ethyl acetate, and the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 3.28 g of intermediate 5A represented by the following formula. The intermediate 5A is a diastereomeric mixture derived from a cyclopropane ring.

Intermediate 5A: ¹ H-NMR (CDCl _3, TMS, δ (ppm)): 7.35-7.28 (2H, m), 7.25-7.21 (1H, m), 7.16- 7.12 (2H, m), 6.40 (1H, s), 4.43 (2H, q), 2.56-2.49 (1H, m), 2.37-2.30 (1H, m), 1.72-1.65 (1H, m), 1.64-1.56 (1H, m), 1.41 (3H, t).

で示される化合物において、Ｇが［表４］に記載のいずれかである化合物。 Reference production example 6
The compounds produced according to the method described in Reference Production Example 5 and their physical properties are shown below.
Formula (III-B)

Wherein G is any of those described in [Table 4].

中間体６Ａ： ¹Ｈ−ＮＭＲ （ＣＤＣｌ_3、ＴＭＳ、δ（ｐｐｍ））：７．３０−７．２２（２Ｈ，ｍ），７．２２−７．１５（１Ｈ，ｍ），７．１２−７．０６（２Ｈ，ｍ），６．４１（１Ｈ，ｓ），４．４４（２Ｈ， ｑ），２．６９−２．５０（２Ｈ，ｍ），２．３１−２．２２（１Ｈ，ｍ），１．６７−１．６０（１Ｈ，ｍ），１．４２（３Ｈ，ｔ），１．４０−１．３４（１Ｈ，ｍ），１．１１−１．０５（１Ｈ， ｍ）．
中間体６Ｂ：¹Ｈ−ＮＭＲ（ＣＤＣｌ_3、ＴＭＳ、δ（ｐｐｍ））：７．３３−７．２９（２Ｈ，ｍ），７．２４−７．２１（３Ｈ，ｍ），６．２８（１Ｈ，ｓ），４．４１（２Ｈ，ｔ），２．８５−２．６９（２Ｈ，ｍ）， ２．００−１．９５（１Ｈ，ｍ），１．７２−１．６２（１Ｈ，ｍ），１．４０（３Ｈ，ｔ），１．２９−１．２４（１Ｈ，ｍ），１．１３−１．０５（１Ｈ，ｍ）．

Intermediate 6A: ¹ H-NMR (CDCl _3, TMS, δ (ppm)): 7.30-7.22 (2H, m), 7.22-7.15 (1H, m), 7.12- 7.06 (2H, m), 6.41 (1H, s), 4.44 (2H, q), 2.69-2.50 (2H, m), 2.31-2.22 (1H, m), 1.67-1.60 (1H, m), 1.42 (3H, t), 1.40-1.34 (1H, m), 1.11-1.05 (1H, m) .
Intermediate 6B: ¹ H-NMR (CDCl _3, TMS, δ (ppm)): 7.33-7.29 (2H, m), 7.24-7.21 (3H, m), 6.28 ( 1H, s), 4.41 (2H, t), 2.85-2.69 (2H, m), 2.00-1.95 (1H, m), 1.72-1.62 (1H, m), 1.40 (3H, t), 1.29-1.24 (1H, m), 1.13-1.05 (1H, m).

中間体７Ａ：１Ｈ−ＮＭＲ（ＣＤＣｌ_3、ＴＭＳ、δ（ｐｐｍ））：７．３５−７．２９（２Ｈ，ｍ），７．２７−７．２１（１Ｈ，ｍ），７．１８−７．１２（２Ｈ，ｍ），６．４７（１Ｈ，ｓ），２．６０−２．５２（１Ｈ，ｍ），２．４０−２．３２（１Ｈ，ｍ），１．７６−１．６８（１Ｈ，ｍ），１．６８−１．５９（１Ｈ，ｍ）． Reference production example 7
To a mixture of 3.1 g of Intermediate 5A and 40 mL of ethanol, 20 mL of 1.2 M aqueous potassium hydroxide solution was added at room temperature and stirred for 1 hour. The mixture was concentrated under reduced pressure to remove ethanol, and diluted hydrochloric acid was added to the resulting residue to adjust to pH 2. The mixture was extracted with ethyl acetate, and the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained solid was washed with a mixed solution of hexane: t-butyl methyl ether = 30: 1 and dried to obtain 2.61 g of a compound represented by the following formula (hereinafter referred to as intermediate 7A). Intermediate 7A is a diastereomeric mixture derived from a cyclopropane ring.

Intermediate 7A: 1H-NMR (CDCl _3, TMS, δ (ppm)): 7.35-7.29 (2H, m), 7.27-7.21 (1H, m), 7.18-7 .12 (2H, m), 6.47 (1H, s), 2.60-2.52 (1H, m), 2.40-2.32 (1H, m), 1.76-1.68 (1H, m), 1.68-1.59 (1H, m).

で示される化合物において、Ｇが［表５］に記載のいずれかである化合物。 Reference production example 8
The compounds produced according to the method described in Reference Production Example 7 and their physical properties are shown below.
Formula (III-C)

In which G is any of those listed in [Table 5].

中間体８Ａ：¹Ｈ−ＮＭＲ（ＣＤＣｌ_3、ＴＭＳ、δ（ｐｐｍ））：９．５５（１Ｈ，ｂｒ ｓ），７．３１−７．２３（２Ｈ，ｍ），７．２２−７．１６（１Ｈ，ｍ），７．１２−７．０５（２Ｈ，ｍ），６．４６（１Ｈ，ｓ），２．６７−２．５６（２Ｈ，ｍ），２．３３−２．２５（１Ｈ，ｍ），１．７３−１．６２（１Ｈ，ｍ），１．４５−１．３７（１Ｈ，ｍ），１．１５−１．０７（１Ｈ，ｍ）．
中間体８Ｂ：¹Ｈ−ＮＭＲ（ＣＤＣｌ_3、ＴＭＳ、δ（ｐｐｍ））：７．３４−７．３０（２Ｈ，ｍ），７．２５−７．２２（３Ｈ，ｍ），６．３５（１Ｈ，ｓ），２．８６−２．７０（２Ｈ，ｍ），２．０２−１．９７ （１Ｈ，ｍ），１．７６−１．６６（１Ｈ，ｍ），１．３４−１．２６（１Ｈ，ｍ），１．１６−１．０９（１Ｈ，ｍ）．

Intermediate 8A: ¹ H-NMR (CDCl _3, TMS, δ (ppm)): 9.55 (1H, brs), 7.31-7.23 (2H, m), 7.22-7.16 (1H, m), 7.12-7.05 (2H, m), 6.46 (1H, s), 2.67-2.56 (2H, m), 2.33-2.25 (1H , M), 1.73-1.62 (1H, m), 1.45-1.37 (1H, m), 1.15-1.07 (1H, m).
Intermediate 8B: ¹ H-NMR (CDCl _3, TMS, δ (ppm)): 7.34-7.30 (2H, m), 7.25-7.22 (3H, m), 6.35 ( 1H, s), 2.86-2.70 (2H, m), 2.02-1.97 (1H, m), 1.76-1.66 (1H, m), 1.34-1. 26 (1H, m), 1.16-1.09 (1H, m).

で示される化合物において、Ｇ及びＲ¹が［表６］に記載のいずれかで示される化合物。 Reference production example 9
The compounds produced according to the method described in Production Example 1 and their physical properties are shown below.
Formula (III-D)

In which G and R ¹ are any one of those described in [Table 6].

中間体９Ａ：¹Ｈ−ＮＭＲ（ＣＤＣｌ₃、ＴＭＳ、δ（ｐｐｍ））：６．２１（１Ｈ，ｓ），３．７５−３．６５（４Ｈ，ｍ），３．２６−３．１６（１Ｈ，ｍ），２．１７−２．０６（２Ｈ，ｍ），１．７２−１．６０（１２Ｈ，ｍ）．
中間体１０Ａ：¹Ｈ−ＮＭＲ（ＣＤＣｌ₃、ＴＭＳ、δ（ｐｐｍ））：６．２０（１Ｈ，ｓ），３．７５−３．６８（４Ｈ，ｍ），２．８５−２．７５（１Ｈ，ｍ），２．１２−２．０５（２Ｈ，ｍ），１．９０−１．２０（１４Ｈ，ｍ）．

Intermediate 9A: ¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 6.21 (1H, s), 3.75-3.65 (4H, m), 3.26-3.16 ( 1H, m), 2.17-2.06 (2H, m), 1.72-1.60 (12H, m).
Intermediate 10A: ¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 6.20 (1H, s), 3.75-3.68 (4H, m), 2.85-2.75 ( 1H, m), 2.12-2.05 (2H, m), 1.90-1.20 (14H, m).

In the compounds represented by formula (Y-1) to formula (Y-678) according to the above production method, a compound wherein Q ¹ is any group selected from the following group (Q-1) (hereinafter referred to as the present invention) (Referred to as compound A).
In the following [Q ¹ ], 3Cy represents a cyclopropyl group, 4Cy represents a cyclobutyl group, 5Cy represents a cyclopentyl group, 6Cy represents a cyclohexyl group, 7Cy represents a cycloheptyl group, and NA1 represents naphthalene-1 -Yl, NA2 represents naphthalen-2-yl, IN1 represents indan-1-yl, IN2 represents indan-2-yl, Py2 represents 2-pyridyl, Qun2 represents 2-quinolyl , Fur2 represents 2-furyl, Thi2 represents 2-thienyl, BF5 represents 5-benzofuranyl, BF2 represents 2-benzofuranyl, BT5 represents 5-benzothienyl, BT2 represents 2-benzothienyl , BDXO5 represents 1,3-benzodioxol-5-yl, BDXA6 represents 1,4-benzodioxan-6-yl, TN represents tetrahydronaphthalen-2-yl, and Py2 represents a 2-pyridyl group Represents In group (Q-1), when the cycloalkyl group has a substituent, the substituent is described together with the substitution position before the symbol. For example, [2- (CH ₂ CH ₂ (2-F-Ph))-3Cy] represents a 2- [2- (2-fluorophenyl) ethyl)] cyclopropyl group, and [3- (CH ₂ CH ₂ (8-F-NA2))-4Cy] represents a 3- [2- (8-fluoronaphthalen-2-yl) ethyl] cyclobutyl group, [2,2-Me ₂ -3-Me-3Cy] Represents a 2,2,3-trimethylcyclopropyl group.

Group (Q-1)
[Q¹] = [3Cy], [2- (CH_Three) -3Cy], [2- (CH₂CH_Three) -3Cy], [2- (CH₂CH₂CH_Three) -3Cy], [2- (3Cy) -3Cy], [2- (CH₂CH₂CH₂CH_Three) -3Cy], [2- (CH₂CHCH_ThreeCH_Three) -3Cy], [2- (CCH_ThreeCH_ThreeCH_Three) -3Cy], [2- (CH₂CH₂CH₂CH₂CH_Three) -3Cy], [2- (CH₂CH₂CH₂CH₂CH₂CH_Three) -3Cy], [2- (CH₂CH₂CH₂CH₂CH₂CH₂CH_Three) -3Cy], [2-F-3Cy], [2,2-F₂-3Cy], [2-Cl-3Cy], [2-Br-3Cy], [2- (OCH_Three) -3Cy], [2- (OCF_Three) -3Cy], [2- (CN) -3Cy], [2- (NO₂) -3Cy], [2- (CHO) -3Cy], [2- (NH₂) -3Cy], [2- (NHMe) -3Cy], [2- (NMe₂) -3Cy], [2- (CF_Three) -3Cy], [2- (CH₂CF_Three) -3Cy], [2- (CH₂CH₂CF_Three) -3Cy], [2- (CH₂CH₂CH₂CF_Three) -3Cy], [2- (CH₂CH₂CH₂CH₂CF_Three) -3Cy], [2-Ph-3Cy], [2- (CH₂Ph) -3Cy], [2- (CH₂CH₂Ph) -3Cy], [2- (CH₂CH₂CH₂Ph) -3Cy], [2- (CH₂CH₂CH₂CH₂Ph) -3Cy], [2- (2-F-Ph) -3Cy], [2- (CH₂(2-F-Ph) -3Cy], [2- (CH₂CH₂(2-F-Ph))-3Cy], [2- (CH₂CH₂CH₂(2-F-Ph))-3Cy], [2- (CH₂CH₂CH₂CH₂(2-F-Ph))-3Cy], [2- (3-F-Ph) -3Cy], [2- (CH₂(4-F-Ph))-3Cy], [2- (CH₂CH₂(2-Cl-Ph))-3Cy], [2- (CH₂CH₂CH₂(3-Cl-Ph))-3Cy], [2- (CH₂CH₂CH₂CH₂(4-Cl-Ph))-3Cy], [2- (2-Br-Ph))-3Cy], [2- (CH₂(4-Br-Ph))-3Cy], [2- (3-Br-5-F-Ph))-3Cy], [2- (CH₂(4-Br-3-F-Ph))-3Cy], [2- (CH₂CH₂(3-Me-Ph))-3Cy], [2- (CH₂CH₂CH₂CH₂(2- (CF_Three-Ph))-3Cy], (2- (CH₂CH₂(3- (CF_Three-Ph))-3Cy], [2- (CH₂CH₂CH₂(4-CF_Three-Ph))-3Cy], [2- (3-OMe-Ph))-3Cy], [2- (CH₂(4-OMe-Ph))-3Cy], [2- (CH₂CH₂(2-OCF_Three-Ph))-3Cy], [2- (CH₂CH₂CH₂(3-OCF_Three-Ph))-3Cy], [2- (CH₂CH₂CH₂CH₂(4-OCF_Three-Ph))-3Cy], [2- (CH₂CH₂(2- (CN-Ph))-3Cy], [2- (CH₂CH₂CH₂(3-NO₂-Ph))-3Cy], [2- (CH₂CH₂CH₂CH₂(4-CHO-Ph))-3Cy], [2- (CH₂(4-NH₂-Ph))-3Cy], [2- (CH₂CH₂(3-NHMe-Ph))-3Cy], [2- (CH₂CH₂CH₂CH₂(2- NMe₂-Ph))-3Cy], (2- (2-SCF_Three-Ph))-3Cy], [2- (CH₂(3-SCF_Three-Ph))-3Cy], [2- (CH₂CH₂(4-SCF_Three-Ph))-3Cy], [2- (NA1) -3Cy], [2- (CH₂(NA1))-3Cy], [2- (CH₂CH₂(NA1))-3Cy], [2- (CH₂CH₂CH₂(NA1))-3Cy], [2- (CH₂CH₂CH₂CH₂(NA1))-3Cy], [2- (NA2) -3Cy], [2- (CH₂(NA2))-3Cy], [2- (CH₂CH₂(NA2))-3Cy], [2- (CH₂CH₂CH₂(NA2))-3Cy], [2- (8-F-NA2) -3Cy], [2- (CH₂(8-F-NA2))-3Cy], [2- (CH₂CH₂(8-F-NA2))-3Cy], [2- (CH₂CH₂CH₂(8-F-NA2))-3Cy], [2- (8-Cl-NA2) -3Cy], [2- (CH₂(8-Cl-NA2))-3Cy], [2- (CH₂CH₂(8-Cl-NA2))-3Cy], [2- (CH₂CH₂CH₂(8-Cl-NA2))-3Cy], [2- (8-Br-NA2))-3Cy], [2- (CH₂(8-Br-NA2))-3Cy], [2- (CH₂CH₂(8-Br-NA2))-3Cy], [2- (CH₂CH₂CH₂(8-Br-NA2))-3Cy], [2- (CH₂CH₂OPh) -3Cy], [2- (CH₂CH₂OCH₂Ph) -3Cy], [2- (CH₂CH₂CH₂OPh) -3Cy], [2- (CH₂CH₂CH₂OCH₂Ph) -3Cy], [2- (CH₂CH₂CH₂CH₂OPh) -3Cy], [2- (CH₂CH₂CH₂CH₂OCH₂Ph) -3Cy], [2- (CH₂CH₂CH₂CH₂CH₂OPh) -3Cy], [2- (CH₂CH₂CH₂CH₂CH₂OCH₂Ph) -3Cy], [2- (CH₂CH₂O (NA2))-3Cy], [2- (CH₂CH₂OCH₂(NA2))-3Cy], [2- (CH₂CH₂CH₂O (NA2))-3Cy], [2- (CH₂CH₂CH₂OCH₂(NA2))-3Cy], [2- (CH₂CH₂CH₂CH₂O (NA2))-3Cy], [2- (CH₂CH₂CH₂CH₂OCH₂(NA2))-3Cy], [2- (CH₂CH₂CH₂CH₂CH₂O (NA2))-3Cy], [2- (CH₂CH₂CH₂CH₂CH₂OCH₂(NA2))-3Cy], (2- (CH₂CH₂(IN1))-3Cy], [2- (CH₂CH₂(IN2))-3Cy], [2- (CH₂CH₂(Py2))-3Cy], [2- (CH₂CH₂(Qun2))-3Cy], [2- (CH₂CH₂(Fur2))-3Cy], [2- (CH₂CH₂(Thi2))-3Cy], [2- (CH₂CH₂(BF5))-3Cy], [2- (CH₂CH₂(BF2))-3Cy], [2- (CH₂CH₂(BT5))-3Cy], [2- (CH₂CH₂(BT2))-3Cy], [2- (CH₂CH₂(BDXO5))-3Cy], [2- (CH₂CH₂(BDXA6))-3Cy], [2- (CH₂(4Cy))-3Cy], [2- (CH₂CH₂(5Cy))-3Cy], [2- (CH₂CH₂(2- (CN) -3Cy))-3Cy], [2- (CH₂CH₂(2,2-F₂-BDXO5))-3Cy], [2- (CH₂CH₂(2,2-F₂) -3Cy) -3Cy], [2- (IN1) -3Cy], [2- (Py2) -3Cy], [2- (Thi2) -3Cy], [2- (CH₂TN) -3Cy], (2,2-Me₂-3Cy], [2,2-Me₂-3-Me-3Cy], [2,2-Me₂-3,3-Me₂-3Cy], [4Cy], [2- (CH_Three) -4Cy], [2- (CH₂CH_Three) -4Cy], [2- (CH₂CH₂CH_Three) -4Cy], [2- (3Cy) -4Cy], [2- (CH₂CH₂CH₂CH_Three) -4Cy], [2- (CH₂CHCH_ThreeCH_Three) -4Cy], [2- (CCH_ThreeCH_ThreeCH_Three) -4Cy], [2- (CH₂CH₂CH₂CH₂CH_Three) -4Cy], [2- (CH₂CH₂CH₂CH₂CH₂CH_Three) -4Cy], [2- (CH₂CH₂CH₂CH₂CH₂CH₂CH_Three) -4Cy], [2-F-4Cy], [2,2-F₂-4Cy], [2-Cl-4Cy], [2-Br-4Cy], [2- (OCH_Three) -4Cy], [2- (OCF_Three) -4Cy], [2- (CN) -4Cy], [2- (NO₂) -4Cy], [2- (CHO) -4Cy], [2- (NH₂) -4Cy], [2- (NHMe) -4Cy], [2- (NMe₂) -4Cy], [2- (CF_Three) -4Cy], [2- (CH₂CF_Three) -4Cy], [2- (CH₂CH₂CF_Three) -4Cy], [2- (CH₂CH₂CH₂CF_Three) -4Cy], [2- (CH₂CH₂CH₂CH₂CF_Three) -4Cy], [2-Ph-4Cy], [2- (CH₂Ph) -4Cy], [2- (CH₂CH₂Ph) -4Cy], [2- (CH₂CH₂CH₂Ph) -4Cy], [2- (CH₂CH₂CH₂CH₂Ph) -4Cy], [2- (2-F-Ph))-4Cy], [2- (CH₂(2-F-Ph))-4Cy], [2- (CH₂CH₂(2-F-Ph))-4Cy], [2- (CH₂CH₂CH₂(2-F-Ph))-4Cy], [2- (CH₂CH₂CH₂CH₂(2-F-Ph))-4Cy], [2- (3-F-Ph))-4Cy], [2- (CH₂(4-F-Ph))-4Cy], [2- (CH₂CH₂(2- (Cl-Ph))-4Cy], [2- (CH₂CH₂CH₂(3- (Cl-Ph))-4Cy], [2- (CH₂CH₂CH₂CH₂(4-Cl-Ph))-4Cy], [2- (2-Br-Ph))-4Cy], [2- (CH₂(4-Br-Ph))-4Cy], [2- (3-Br-5-F-Ph))-4Cy], [2- (CH₂(4-Br-3-F-Ph))-4Cy], [2- (CH₂CH₂(3-Me-Ph))-4Cy], [2- (CH₂CH₂CH₂CH₂(2-CF_Three-Ph))-4Cy], (2- (CH₂CH₂(3-CF_Three-Ph))-4Cy], [2- (CH₂CH₂CH₂(4-CF_Three-Ph))-4Cy], [2- (3-OMe-Ph))-4Cy], [2- (CH₂(4-OMe-Ph))-4Cy], [2- (CH₂CH₂(2-OCF_Three-Ph))-4Cy], [2- (CH₂CH₂CH₂(3-OCF_Three-Ph))-4Cy], [2- (CH₂CH₂CH₂CH₂(4-OCF_Three-Ph))-4Cy], [2- (CH₂CH₂(2- (CN-Ph))-4Cy], [2- (CH₂CH₂CH₂(3-NO₂-Ph))-4Cy], [2- (CH₂CH₂CH₂CH₂(4-CHO-Ph))-4Cy], [2- (CH₂(4-NH₂-Ph))-4Cy], [2- (CH₂CH₂(3-NHMe-Ph))-4Cy], [2- (CH₂CH₂CH₂CH₂(2- NMe₂-Ph))-4Cy], (2- (2-SCF_Three-Ph))-4Cy], [2- (CH₂(3-SCF_Three-Ph))-4Cy], [2- (CH₂CH₂(4-SCF_Three-Ph))-4Cy], [2- (NA1) -4Cy], [2- (CH₂(NA1))-4Cy], [2- (CH₂CH₂(NA1))-4Cy], [2- (CH₂CH₂CH₂(NA1))-4Cy], [2- (CH₂CH₂CH₂CH₂(NA1))-4Cy], [2- (NA2) -4Cy], [2- (CH₂(NA2))-4Cy], [2- (CH₂CH₂(NA2))-4Cy], [2- (CH₂CH₂CH₂(NA2))-4Cy], [2- (8-F-NA2) -4Cy], [2- (CH₂(8-F-NA2))-4Cy], [2- (CH₂CH₂(8-F-NA2))-4Cy], [2- (CH₂CH₂CH₂(8-F-NA2))-4Cy], [2- (8-Cl-NA2) -4Cy], [2- (CH₂(8-Cl-NA2))-4Cy], [2- (CH₂CH₂(8-Cl-NA2))-4Cy], [2- (CH₂CH₂CH₂(8-Cl-NA2))-4Cy], [2- (8-Br-NA2))-4Cy], [2- (CH₂(
8-Br-NA2))-4Cy], [2- (CH₂CH₂(8-Br-NA2))-4Cy], [2- (CH₂CH₂CH₂(8-Br-NA2))-4Cy], [2- (CH₂CH₂OPh) -4Cy], [2- (CH₂CH₂OCH₂Ph) -4Cy], [2- (CH₂CH₂CH₂OPh) -4Cy], [2- (CH₂CH₂CH₂OCH₂Ph) -4Cy], [2- (CH₂CH₂CH₂CH₂OPh) -4Cy], [2- (CH₂CH₂CH₂CH₂OCH₂Ph) -4Cy], [2- (CH₂CH₂CH₂CH₂CH₂OPh) -4Cy], [2- (CH₂CH₂CH₂CH₂CH₂OCH₂Ph) -4Cy], [2- (CH₂CH₂O (NA2))-4Cy], [2- (CH₂CH₂OCH₂(NA2))-4Cy], [2- (CH₂CH₂CH₂O (NA2))-4Cy], [2- (CH₂CH₂CH₂OCH₂(NA2))-4Cy], [2- (CH₂CH₂CH₂CH₂O (NA2))-4Cy], [2- (CH₂CH₂CH₂CH₂OCH₂(NA2))-4Cy], [2- (CH₂CH₂CH₂CH₂CH₂O (NA2))-4Cy], [2- (CH₂CH₂CH₂CH₂CH₂OCH₂(NA2))-4Cy], (2- (CH₂CH₂(IN1))-4Cy], [2- (CH₂CH₂(IN2))-4Cy], [2- (CH₂CH₂(Py2))-4Cy], [2- (CH₂CH₂(Qun2))-4Cy], [2- (CH₂CH₂(Fur2))-4Cy], [2- (CH₂CH₂(Thi2))-4Cy], [2- (CH₂CH₂(BF5))-4Cy], [2- (CH₂CH₂(BF2))-4Cy], [2- (CH₂CH₂(BT5))-4Cy], [2- (CH₂CH₂(BT2))-4Cy], [2- (CH₂CH₂(BDXO5))-4Cy], [2- (CH₂CH₂(BDXA6))-4Cy], [2- (CH₂(4Cy))-4Cy], [2- (CH₂CH₂(5Cy))-4Cy], [2- (CH₂CH₂(2- (CN) -3Cy))-4Cy], [2- (CH₂CH₂(2,2-F₂-BDXO5))-4Cy], [2- (CH₂CH₂(2,2-F₂) -3Cy) -4Cy], [2- (IN1) -4Cy], [2- (Py2) -4Cy], [2- (Thi2) -4Cy], [2- (CH₂TN) -4Cy], (3- (CH_Three) -4Cy], [3- (CH₂CH_Three) -4Cy], [3- (CH₂CH₂CH_Three) -4Cy], [3- (3Cy) -4Cy], [3- (CH₂CH₂CH₂CH_Three) -4Cy], [3- (CH₂CHCH_ThreeCH_Three) -4Cy], [3- (CCH_ThreeCH_ThreeCH_Three) -4Cy], [3- (CH₂CH₂CH₂CH₂CH_Three) -4Cy], [3- (CH₂CH₂CH₂CH₂CH₂CH_Three) -4Cy], [3- (CH₂CH₂CH₂CH₂CH₂CH₂CH_Three) -4Cy], [3-F-4Cy], [3,3-F₂-4Cy], [3-Cl-4Cy], [3-Br-4Cy], [3- (OCH_Three) -4Cy], [3- (OCF_Three) -4Cy], [3- (CN) -4Cy], [3- (NO₂) -4Cy], [3- (CHO) -4Cy], [3- (NH₂) -4Cy], [3- (NHMe) -4Cy], [3- (NMe₂) -4Cy], [3- (CF_Three) -4Cy], [3- (CH₂CF_Three) -4Cy], [3- (CH₂CH₂CF_Three) -4Cy], [3- (CH₂CH₂CH₂CF_Three) -4Cy], [3- (CH₂CH₂CH₂CH₂CF_Three) -4Cy], [3-Ph-4Cy], [3- (CH₂Ph) -4Cy], [3- (CH₂CH₂Ph) -4Cy], [3- (CH₂CH₂CH₂Ph) -4Cy], [3- (CH₂CH₂CH₂CH₂Ph) -4Cy], [3- (2-F-Ph))-4Cy], [3- (CH₂(2-F-Ph))-4Cy], [3- (CH₂CH₂(2-F-Ph))-4Cy], [3- (CH₂CH₂CH₂(2-F-Ph))-4Cy], [3- (CH₂CH₂CH₂CH₂(2-F-Ph))-4Cy], [3- (3-F-Ph))-4Cy], [3- (CH₂(4-F-Ph))-4Cy], [3- (CH₂CH₂(2- (Cl-Ph))-4Cy], [3- (CH₂CH₂CH₂(3- (Cl-Ph))-4Cy], [3- (CH₂CH₂CH₂CH₂(4-Cl-Ph))-4Cy], [3- (2-Br-Ph))-4Cy], [3- (CH₂(4-Br-Ph))-4Cy], [3-3-Br-5-F-Ph) -4Cy], [3- (CH₂(4-Br-3-F-Ph))-4Cy], [3- (CH₂CH₂(3-Me-Ph))-4Cy], [3- (CH₂CH₂CH₂CH₂(2-CF_Three-Ph))-4Cy], (3- (CH₂CH₂(3-CF_Three-Ph))-4Cy], [3- (CH₂CH₂CH₂(4-CF_Three-Ph))-4Cy], [3- (3-OMe-Ph))-4Cy], [3- (CH₂(4-OMe-Ph))-4Cy], [3- (CH₂CH₂(2-OCF_Three-Ph))-4Cy], [3- (CH₂CH₂CH₂(3-OCF_Three-Ph))-4Cy], [3- (CH₂CH₂CH₂CH₂(4-OCF_Three-Ph))-4Cy], [3- (CH₂CH₂(2- (CN-Ph))-4Cy], [3- (CH₂CH₂CH₂(3-NO₂-Ph))-4Cy], [3- (CH₂CH₂CH₂CH₂(4-CHO-Ph))-4Cy], [3- (CH₂(4-NH₂-Ph))-4Cy], [3- (CH₂CH₂(3-NHMe-Ph))-4Cy], [3- (CH₂CH₂CH₂CH₂(2- NMe₂-Ph))-4Cy], (3- (2-SCF_Three-Ph))-4Cy], [3- (CH₂(3-SCF_Three-Ph))-4Cy], [3- (CH₂CH₂(4-SCF_Three-Ph))-4Cy], [3- (NA1) -4Cy], [3- (CH₂(NA1))-4Cy], [3- (CH₂CH₂(NA1))-4Cy], [3- (CH₂CH₂CH₂(NA1))-4Cy], [3- (CH₂CH₂CH₂CH₂(NA1))-4Cy], [3- (NA2) -4Cy], [3- (CH₂(NA2))-4Cy], [3- (CH₂CH₂(NA2))-4Cy], [3- (CH₂CH₂CH₂(NA2))-4Cy], [3- (8-F-NA2))-4Cy], [3- (CH₂(8-F-NA2))-4Cy], [3- (CH₂CH₂(8-F-NA2))-4Cy], [3- (CH₂CH₂CH₂(8-F-NA2))-4Cy], [3- (8-Cl-NA2) -4Cy], [3- (CH₂(8-Cl-NA2))-4Cy], [3- (CH₂CH₂(8-Cl-NA2))-4Cy], [3- (CH₂CH₂CH₂(8-Cl-NA2))-4Cy], [3- (8-Br-NA2))-4Cy], [3- (CH₂(8-Br-NA2))-4Cy], [3- (CH₂CH₂(8-Br-NA2))-4Cy], [3- (CH₂CH₂CH₂(8-Br-NA2))-4Cy], [3- (CH₂CH₂OPh) -4Cy], [3- (CH₂CH₂OCH₂Ph) -4Cy], [3- (CH₂CH₂CH₂OPh) -4Cy], [3- (CH₂CH₂CH₂OCH₂Ph) -4Cy], [3- (CH₂CH₂CH₂CH₂OPh) -4Cy], [3- (CH₂CH₂CH₂CH₂OCH₂Ph) -4Cy], [3- (CH₂CH₂CH₂CH₂CH₂OPh) -4Cy], [3- (CH₂CH₂CH₂CH₂CH₂OCH₂Ph) -4Cy], [3- (CH₂CH₂O (NA2))-4Cy], [3- (CH₂CH₂OCH₂(NA2))-4Cy], [3- (CH₂CH₂CH₂O (NA2))-4Cy], [3- (CH₂CH₂CH₂OCH₂(NA2))-4Cy], [3- (CH₂CH₂CH₂CH₂O (NA2))-4Cy], [3- (CH₂CH₂CH₂CH₂OCH₂(NA2))-4Cy], [3- (CH₂CH₂CH₂CH₂CH₂O (NA2))-4Cy], [3- (CH₂CH₂CH₂CH₂CH₂OCH₂(NA2))-4Cy], (3- (CH₂CH₂(IN1))-4Cy], [3- (CH₂CH₂(IN2))-4Cy], [3- (CH₂CH₂(Py2))-4Cy], [3- (CH₂CH₂(Qun2))-4Cy], [3- (CH₂CH₂(Fur2))-4Cy], [3- (CH₂CH₂(Thi2))-4Cy], [3- (CH₂CH₂(BF5))-4Cy], [3- (CH₂CH₂(BF2))-4Cy], [3- (CH₂CH₂(BT5))-4Cy], [3- (CH₂CH₂(BT2))-4Cy], [3- (CH₂CH₂(BDXO5))-4Cy], [3- (CH₂CH₂(BDXA6))-4Cy], [3- (CH₂(4Cy))-4Cy], [3- (CH₂CH₂(5Cy))-4Cy], [3- (CH₂CH₂(2- (CN) -3Cy))-4Cy], [3- (CH₂CH₂(2,2-F₂-BDXO5))-4Cy], [3- (CH₂CH₂(2,2-F₂) -3Cy))-4Cy], [3- (IN1) -4Cy], [3- (Py2) -4Cy], [3- (Thi2) -4Cy], [3- (CH₂TN) -4Cy], (2-Me-3-Me-4Cy), (2,2-Me₂-4Cy], [3,3-Me₂-4Cy], [2-Me-3-Me-4-Me-4Cy], [2,2-Me₂-3,3-Me₂-4,4-Me₂-4Cy], [5Cy], [2- (CH_Three) -5Cy], [2- (CH₂CH_Three) -5Cy], [2- (CH₂CH₂CH_Three) -5Cy], [2- (3Cy) -5Cy], [2- (CH₂CH₂CH₂CH_Three) -5Cy], [2- (CH₂CHCH_ThreeCH_Three) -5Cy], [2- (CCH_ThreeCH_ThreeCH_Three) -5Cy], [2- (CH₂CH₂CH₂CH₂CH_Three) -5Cy], [2- (CH₂CH₂CH₂CH₂CH₂CH_Three) -5Cy], [2- (CH₂CH₂CH₂CH₂CH₂CH₂CH_Three) -5Cy], [2-F-5Cy], [2- (OCH_Three) -5Cy], [2- (OCF_Three) -5Cy], [2- (CN) -5Cy], [2- (NMe₂) -5Cy], [2- (CF_Three) -5Cy], [2- (CH₂CF_Three) -5Cy], [2- (CH₂CH₂CF_Three) -5Cy], [2- (CH₂CH₂CH₂CF_Three) -5Cy], [2- (CH₂CH₂CH₂CH₂CF_Three) -5Cy], [2-Ph-5Cy], [2- (CH₂Ph) -5Cy], [2- (CH₂CH₂Ph) -5Cy], [2- (CH₂CH₂CH₂Ph) -5Cy], [2- (CH₂CH₂CH₂CH₂Ph) -5Cy], [2- (2-F-Ph))-5Cy], [2- (CH₂(4-F-Ph))-5Cy], [2- (CH₂CH₂(2-Cl-Ph))-5Cy], [2- (CH₂CH₂CH₂(4-CF_Three-Ph))-5Cy], [2- (CH₂CH₂CH₂CH₂(4-OCF_Three-Ph))-5Cy], [2- (NA1) -5Cy], [2- (CH₂(NA1))-5Cy], [2- (CH₂CH₂(NA2))-5Cy], [2- (CH₂CH₂CH
₂(NA2))-5Cy], [2- (8-F-NA2))-5Cy], [2- (CH₂CH₂OPh) -5Cy], [2- (CH₂CH₂CH₂CH₂CH₂OCH₂(NA2))-5Cy], (2- (CH₂CH₂(IN1))-5Cy], [2- (CH₂CH₂(IN2))-5Cy], [2- (CH₂CH₂(Py2))-5Cy], [2- (CH₂CH₂(Qun2))-5Cy], [2- (CH₂CH₂(Fur2))-5Cy], [2- (CH₂CH₂(Thi2))-5Cy], [2- (CH₂CH₂(BF5))-5Cy], [2- (CH₂CH₂(BF2))-5Cy], [2- (CH₂CH₂(BT5))-5Cy], [2- (CH₂CH₂(BT2))-5Cy], [2- (CH₂CH₂(BDXO5))-5Cy], [2- (CH₂CH₂(BDXA6))-5Cy], [2- (CH₂(4Cy))-5Cy], [2- (CH₂CH₂(5Cy))-5Cy] (2- (CH₂CH₂(2,2-F₂) -3Cy) -5Cy], [2- (CH₂CH₂(2- (CN) -3Cy))-5Cy], [2- (CH₂CH₂(2,2-F₂-BDXO5))-5Cy], [2- (IN1) -5Cy], [2- (Py2) -5Cy], [2- (Thi2) -5Cy], [2- (CH₂TN) -5Cy], (3- (CH_Three) -5Cy], [3- (CH₂CH_Three) -5Cy], [3- (CH₂CH₂CH_Three) -5Cy], [3- (3Cy) -5Cy], [3- (CH_{2- (C}H₂CH_{2- (C}H_Three) -5Cy], [3- (CH₂CHCH_ThreeCH_Three) -5Cy], [3- (CCH_ThreeCH_ThreeCH_Three) -5Cy], [3- (CH₂CH₂CH₂CH₂CH_Three) -5Cy], [3- (CH₂CH₂CH₂CH₂CH₂CH_Three) -5Cy], [3- (CH₂CH₂CH₂CH₂CH₂CH₂CH_Three) -5Cy], [3-F-5Cy], [3- (OCH_Three) -5Cy], [3- (OCF_Three) -5Cy], [3- (CN) -5Cy], [3- (NMe₂) -5Cy], [3- (CF_Three) -5Cy], [3- (CH₂CF_Three) -5Cy], [3- (CH₂CH₂CF_Three) -5Cy], [3- (CH₂CH₂CH₂CF_Three) -5Cy], [3- (CH₂CH₂CH₂CH₂CF_Three) -5Cy], [3-Ph-5Cy], [3- (CH₂Ph) -5Cy], [3- (CH₂CH₂Ph) -5Cy], [3- (CH₂CH₂CH₂Ph) -5Cy], [3- (CH₂CH₂CH₂CH₂Ph) -5Cy], [3- (2-F-Ph))-5Cy], [3- (CH₂(4-F-Ph))-5Cy], [3- (CH₂CH₂(2- (Cl-Ph))-5Cy], [3- (CH₂CH₂CH₂(4-CF_Three-Ph))-5Cy], [3- (CH₂CH₂CH₂CH₂(4-OCF_Three-Ph))-5Cy], [3- (NA1) -5Cy], [3- (CH₂(NA1))-5Cy], [3- (CH₂CH₂(NA2))-5Cy], [3- (CH₂CH₂CH₂(NA2))-5Cy], [3- (8-F-NA2))-5Cy], [3- (CH₂CH₂OPh) -5Cy], [3- (CH₂CH₂CH₂CH₂CH₂OCH₂(NA2))-5Cy], (3- (CH₂CH₂(IN1))-5Cy], [3- (CH₂CH₂(IN2))-5Cy], [3- (CH₂CH₂(Py2))-5Cy], [3- (CH₂CH₂(Qun2))-5Cy], [3- (CH₂CH₂(Fur2))-5Cy], [3- (CH₂CH₂(Thi2))-5Cy], [3- (CH₂CH₂(BF5))-5Cy], [3- (CH₂CH₂(BF2))-5Cy], [3- (CH₂CH₂(BT5))-5Cy], [3- (CH₂CH₂(BT2))-5Cy], [3- (CH₂CH₂(BDXO5))-5Cy], [3- (CH₂CH₂(BDXA6))-5Cy], [3- (CH₂(4Cy))-5Cy], [3- (CH₂CH₂(5Cy))-5Cy] (3- (CH₂CH₂(2,2-F₂) -3Cy) -5Cy], [3- (CH₂CH₂(2- (CN) -3Cy))-5Cy], [3- (CH₂CH₂(2,2-F₂-BDXO5))-5Cy], [3- (IN1) -5Cy], [3- (Py2) -5Cy], [3- (Thi2) -5Cy], [3- (CH₂TN) -5Cy], [6Cy], [2- (CH_Three) -6Cy], [2- (CH₂CH_Three) -6Cy], [2- (CH₂CH₂CH_Three) -6Cy], [2- (3Cy) -6Cy], [2- (CH₂CH₂CH₂CH_Three) -6Cy], [2- (CH₂CHCH_ThreeCH_Three) -6Cy], [2- (CCH_ThreeCH_ThreeCH_Three) -6Cy], [2- (CH₂CH₂CH₂CH₂CH_Three) -6Cy], [2- (CH₂CH₂CH₂CH₂CH₂CH_Three) -6Cy], [2- (CH₂CH₂CH₂CH₂CH₂CH₂CH_Three) -6Cy], [2-F-6Cy], [2- (OCH_Three) -6Cy], [2- (OCF_Three) -6Cy], [2- (CN) -6Cy], [2- (NMe₂) -6Cy], [2- (CF_Three) -6Cy], [2- (CH₂CF_Three) -6Cy], [2- (CH₂CH₂CF_Three) -6Cy], [2- (CH₂CH₂CH₂CF_Three) -6Cy], [2- (CH₂CH₂CH₂CH₂CF_Three) -6Cy], [2-Ph-6Cy], [2- (CH₂Ph) -6Cy], [2- (CH₂CH₂Ph) -6Cy], [2- (CH₂CH₂CH₂Ph) -6Cy], [2- (CH₂CH₂CH₂CH₂Ph) -6Cy], [2- (2-F-Ph))-6Cy], [2- (CH₂(4-F-Ph))-6Cy], [2- (CH₂CH₂(2- (Cl-Ph))-6Cy], [2- (CH₂CH₂CH₂(4-CF_Three-Ph))-6Cy], [2- (CH₂CH₂CH₂CH₂(4-OCF_Three-Ph))-6Cy], [2- (NA1) -6Cy], [2- (CH₂(NA1))-6Cy], [2- (CH₂CH₂(NA2))-6Cy], [2- (CH₂CH₂CH₂(NA2))-6Cy], [2- (8-F-NA2))-6Cy], [2- (CH₂CH₂OPh) -6Cy], [2- (CH₂CH₂CH₂CH₂CH₂OCH₂(NA2))-6Cy], (2- (CH₂CH₂(IN1))-6Cy], [2- (CH₂CH₂(IN2))-6Cy], [2- (CH₂CH₂(Py2))-6Cy], [2- (CH₂CH₂(Qun2))-6Cy], [2- (CH₂CH₂(Fur2))-6Cy], [2- (CH₂CH₂(Thi2))-6Cy], [2- (CH₂CH₂(BF5))-6Cy], [2- (CH₂CH₂(BF2))-6Cy], [2- (CH₂CH₂(BT5))-6Cy], [2- (CH₂CH₂(BT2))-6Cy], [2- (CH₂CH₂(BDXO5))-6Cy], [2- (CH₂CH₂(BDXA6))-6Cy], [2- (CH₂(4Cy))-6Cy], [2- (CH₂CH₂(5Cy))-6Cy] (2- (CH₂CH₂(2,2-F₂) -3Cy) -6Cy], [2- (CH₂CH₂(2- (CN) -3Cy))-6Cy], [2- (CH₂CH₂(2,2-F₂-BDXO5))-6Cy], [2- (IN1) -6Cy], [2- (Py2) -6Cy], [2- (Thi2) -6Cy], [2- (CH₂TN) -6Cy], (3- (CH_Three) -6Cy], [3- (CH₂CH_Three) -6Cy], [3- (CH₂CH₂CH_Three) -6Cy], [3- (3Cy) -6Cy], [3- (CH₂CH₂CH₂CH_Three) -6Cy], [3- (CH₂CHCH_ThreeCH_Three) -6Cy], [3- (CCH_ThreeCH_ThreeCH_Three) -6Cy], [3- (CH₂CH₂CH₂CH₂CH_Three) -6Cy], [3- (CH₂CH₂CH₂CH₂CH₂CH_Three) -6Cy], [3- (CH₂CH₂CH₂CH₂CH₂CH₂CH_Three) -6Cy], [3-F-6Cy], [3- (OCH_Three) -6Cy], [3- (OCF_Three) -6Cy], [3- (CN) -6Cy], [3- (NMe₂) -6Cy], [3- (CF_Three) -6Cy], [3- (CH₂CF_Three) -6Cy], [3- (CH₂CH₂CF_Three) -6Cy], [3- (CH₂CH₂CH₂CF_Three) -6Cy], [3- (CH₂CH₂CH₂CH₂CF_Three) -6Cy], [3-Ph-6Cy], [3- (CH₂Ph) -6Cy], [3- (CH₂CH₂Ph) -6Cy], [3- (CH₂CH₂CH₂Ph) -6Cy], [3- (CH₂CH₂CH₂CH₂Ph) -6Cy], [3- (2-F-Ph))-6Cy], [3- (CH₂(4-F-Ph))-6Cy], [3- (CH₂CH₂(2- (Cl-Ph))-6Cy], [3- (CH₂CH₂CH₂(4-CF_Three-Ph))-6Cy], [3- (CH₂CH₂CH₂CH₂(4-OCF_Three-Ph))-6Cy], [3- (NA1) -6Cy], [3- (CH₂(NA1))-6Cy], [3- (CH₂CH₂(NA2))-6Cy], [3- (CH₂CH₂CH₂(NA2))-6Cy], [3- (8-F-NA2))-6Cy], [3- (CH₂CH₂OPh) -6Cy], [3- (CH₂CH₂CH₂CH₂CH₂OCH₂(NA2))-6Cy], (3- (CH₂CH₂(IN1))-6Cy], [3- (CH₂CH₂(IN2))-6Cy], [3- (CH₂CH₂(Py2))-6Cy], [3- (CH₂CH₂(Qun2))-6Cy], [3- (CH₂CH₂(Fur2))-6Cy], [3- (CH₂CH₂(Thi2))-6Cy], [3- (CH₂CH₂(BF5))-6Cy], [3- (CH₂CH₂(BF2))-6Cy], [3- (CH₂CH₂(BT5))-6Cy], [3- (CH₂CH₂(BT2))-6Cy], [3- (CH₂CH₂(BDXO5))-6Cy], [3- (CH₂CH₂(BDXA6))-6Cy], [3- (CH₂(4Cy))-6Cy], [3- (CH₂CH₂(5Cy))-6Cy] (3- (CH₂CH₂(2,2-F₂) -3Cy) -6Cy], [3- (CH₂CH₂(2- (CN) -3Cy))-6Cy], [3- (CH₂CH₂(2,2-F₂-BDXO5))-6Cy], [3- (IN1) -6Cy], [3- (Py2) -6Cy], [3- (Thi2) -6Cy], [3- (CH₂TN) -6Cy], (4- (CH_Three) -6Cy], [4- (CH₂CH_Three) -6Cy], [4- (CH₂CH₂CH_Three) -6Cy], [4- (3Cy) -6Cy], [4- (CH₂CH₂CH₂CH_Three) -6Cy], [4- (CH₂CHCH_ThreeCH_Three) -6Cy], [4- (CCH_ThreeCH_ThreeCH_Three) -6Cy], [4- (CH₂CH₂CH₂CH₂CH_Three) -6Cy], [4- (CH₂CH₂CH₂CH₂CH₂CH_Three) -6Cy], [4- (CH₂CH₂CH₂CH₂CH₂CH₂CH_Three) -6Cy], [4-F-6Cy], [4- (OCH_Three) -6Cy], [4- (OCF_Three) -6Cy], [4- (CN) -6Cy], [4- (NMe₂) -6Cy], [4- (CF_Three) -6Cy], [4- (CH₂CF_Three
) -6Cy], [4- (CH₂CH₂CF_Three) -6Cy], [4- (CH₂CH₂CH₂CF_Three) -6Cy], [4- (CH₂CH₂CH₂CH₂CF_Three) -6Cy], [4-Ph-6Cy], [4- (CH₂Ph) -6Cy], [4- (CH₂CH₂Ph) -6Cy], [4- (CH₂CH₂CH₂Ph) -6Cy], [4- (CH₂CH₂CH₂CH₂Ph) -6Cy], [4- (2-F-Ph) -6Cy], [4- (CH₂(4-F-Ph))-6Cy], [4- (CH₂CH₂(2- (Cl-Ph))-6Cy], [4- (CH₂CH₂CH₂(4-CF_Three-Ph))-6Cy], [4- (CH₂CH₂CH₂CH₂(4-OCF_Three-Ph))-6Cy], [4- (NA1) -6Cy], [4- (CH₂(NA1))-6Cy], [4- (CH₂CH₂(NA2))-6Cy], [4- (CH₂CH₂CH₂(NA2))-6Cy], [4- (8-F-NA2))-6Cy], [4- (CH₂CH₂OPh) -6Cy], [4- (CH₂CH₂CH₂CH₂CH₂OCH₂(NA2))-6Cy], (4- (CH₂CH₂(IN1))-6Cy], [4- (CH₂CH₂(IN2))-6Cy], [4- (CH₂CH₂(Py2))-6Cy], [4- (CH₂CH₂(Qun2))-6Cy], [4- (CH₂CH₂(Fur2))-6Cy], [4- (CH₂CH₂(Thi2))-6Cy], [4- (CH₂CH₂(BF5))-6Cy], [4- (CH₂CH₂(BF2))-6Cy], [4- (CH₂CH₂(BT5))-6Cy], [4- (CH₂CH₂(BT2))-6Cy], [4- (CH₂CH₂(BDXO5))-6Cy], [4- (CH₂CH₂(BDXA6))-6Cy], [4- (CH₂(4Cy))-6Cy], [4- (CH₂CH₂(5Cy))-6Cy] (4- (CH₂CH₂(2,2-F₂) -3Cy) -6Cy], [4- (CH₂CH₂(2- (CN) -3Cy))-6Cy], [4- (CH₂CH₂(2,2-F₂-BDXO5))-6Cy], [4- (IN1) -6Cy], [4- (Py2) -6Cy], [4- (Thi2) -6Cy], [4- (CH₂TN) -6Cy], [7Cy], [2- (CH_Three) -7Cy], [2- (CH₂CH_Three) -7Cy], [2- (CH₂CH₂CH_Three) -7Cy], [2- (3Cy) -7Cy], [2- (CH₂CH₂CH₂CH_Three) -7Cy], [2- (CH₂CHCH_ThreeCH_Three) -7Cy], [2- (CCH_ThreeCH_ThreeCH_Three) -7Cy], [2- (CH₂CH₂CH₂CH₂CH_Three) -7Cy], [2- (CH₂CH₂CH₂CH₂CH₂CH_Three) -7Cy], [2- (CH₂CH₂CH₂CH₂CH₂CH₂CH_Three) -7Cy], [2-F-7Cy], [2- (OCH_Three) -7Cy], [2- (OCF_Three) -7Cy], [2- (CN) -7Cy], [2- (NMe₂) -7Cy], [2- (CF_Three) -7Cy], [2- (CH₂CF_Three) -7Cy], [2- (CH₂CH₂CF_Three) -7Cy], [2- (CH₂CH₂CH₂CF_Three) -7Cy], [2- (CH₂CH₂CH₂CH₂CF_Three) -7Cy], [2-Ph-7Cy], [2- (CH₂Ph) -7Cy], [2- (CH₂CH₂Ph) -7Cy], [2- (CH₂CH₂CH₂Ph) -7Cy], [2- (CH₂CH₂CH₂CH₂Ph) -7Cy], [2- (2-F-Ph))-7Cy], [2- (CH₂(4-F-Ph))-7Cy], [2- (CH₂CH₂(2- (Cl-Ph))-7Cy], [2- (CH₂CH₂CH₂(4-CF_Three-Ph))-7Cy], [2- (CH₂CH₂CH₂CH₂(4-OCF_Three-Ph))-7Cy], [2- (NA1) -7Cy], [2- (CH₂(NA1))-7Cy], [2- (CH₂CH₂(NA2))-7Cy], [2- (CH₂CH₂CH₂(NA2))-7Cy], [2- (8-F-NA2))-7Cy], [2- (CH₂CH₂OPh) -7Cy], [2- (CH₂CH₂CH₂CH₂CH₂OCH₂(NA2))-7Cy], (2- (CH₂CH₂(IN1))-7Cy], [2- (CH₂CH₂(IN2))-7Cy], [2- (CH₂CH₂(Py2))-7Cy], [2- (CH₂CH₂(Qun2))-7Cy], [2- (CH₂CH₂(Fur2))-7Cy], [2- (CH₂CH₂(Thi2))-7Cy], [2- (CH₂CH₂(BF5))-7Cy], [2- (CH₂CH₂(BF2))-7Cy], [2- (CH₂CH₂(BT5))-7Cy], [2- (CH₂CH₂(BT2))-7Cy], [2- (CH₂CH₂(BDXO5))-7Cy], [2- (CH₂CH₂(BDXA6))-7Cy], [2- (CH₂(4Cy))-7Cy], [2- (CH₂CH₂(5Cy))-7Cy] (2- (CH₂CH₂(2,2-F₂) -3Cy) -7Cy], [2- (CH₂CH₂(2- (CN) -3Cy))-7Cy], [2- (CH₂CH₂(2,2-F₂-BDXO5))-7Cy], [2- (IN1) -7Cy], [2- (Py2) -7Cy], [2- (Thi2) -7Cy], [2- (CH₂TN) -7Cy], (3- (CH_Three) -7Cy], [3- (CH₂CH_Three) -7Cy], [3- (CH₂CH₂CH_Three) -7Cy], [3- (3Cy) -7Cy], [3- (CH₂CH₂CH₂CH_Three) -7Cy], [3- (CH₂CHCH_ThreeCH_Three) -7Cy], [3- (CCH_ThreeCH_ThreeCH_Three) -7Cy], [3- (CH₂CH₂CH₂CH₂CH_Three) -7Cy], [3- (CH₂CH₂CH₂CH₂CH₂CH_Three) -7Cy], [3- (CH₂CH₂CH₂CH₂CH₂CH₂CH_Three) -7Cy], [3-F-7Cy], [3- (OCH_Three) -7Cy], [3- (OCF) -7Cy], [3- (CN) -7Cy], [3- (NMe₂) -7Cy], [3- (CF_Three) -7Cy], [3- (CH₂CF_Three) -7Cy], [3- (CH₂CH₂CF_Three) -7Cy], [3- (CH₂CH₂CH₂CF_Three) -7Cy], [3- (CH₂CH₂CH₂CH₂CF_Three) -7Cy], [3-Ph-7Cy], [3- (CH₂Ph) -7Cy], [3- (CH₂CH₂Ph) -7Cy], [3- (CH₂CH₂CH₂Ph) -7Cy], [3- (CH₂CH₂CH₂CH₂Ph) -7Cy], [3- (2-F-Ph))-7Cy], [3- (CH₂(4-F-Ph))-7Cy], [3- (CH₂CH₂(2- (Cl-Ph))-7Cy], [3- (CH₂CH₂CH₂(4-CF_Three-Ph))-7Cy], [3- (CH₂CH₂CH₂CH₂(4-OCF_Three-Ph))-7Cy], [3- (NA1) -7Cy], [3- (CH₂(NA1))-7Cy], [3- (CH₂CH₂(NA2))-7Cy], [3- (CH₂CH₂CH₂(NA2))-7Cy], [3- (8-F-NA2))-7Cy], [3- (CH₂CH₂OPh) -7Cy], [3- (CH₂CH₂CH₂CH₂CH₂OCH₂(NA2))-7Cy], (3- (CH₂CH₂(IN1))-7Cy], [3- (CH₂CH₂(IN2))-7Cy], [3- (CH₂CH₂(Py2))-7Cy], [3- (CH₂CH₂(Qun2))-7Cy], [3- (CH₂CH₂(Fur2))-7Cy], [3- (CH₂CH₂(Thi2))-7Cy], [3- (CH₂CH₂(BF5))-7Cy], [3- (CH₂CH₂(BF2))-7Cy], [3- (CH₂CH₂(BT5))-7Cy], [3- (CH₂CH₂(BT2))-7Cy], [3- (CH₂CH₂(BDXO5))-7Cy], [3- (CH₂CH₂(BDXA6))-7Cy], [3- (CH₂(4Cy))-7Cy], [3- (CH₂CH₂(5Cy))-7Cy] (3- (CH₂CH₂(2,2-F₂) -3Cy) -7Cy], [3- (CH₂CH₂(2- (CN) -3Cy))-7Cy], [3- (CH₂CH₂(2,2-F₂-BDXO5))-7Cy], [3- (IN1) -7Cy], [3- (Py2) -7Cy], [3- (Thi2) -7Cy], [3- (CH₂TN) -7Cy], (4- (CH_Three) -7Cy], [4- (CH₂CH_Three) -7Cy], [4- (CH₂CH₂CH_Three) -7Cy], [4- (3Cy) -7Cy], [4- (CH₂CH₂CH₂CH_Three) -7Cy], [4- (CH₂CHCH_ThreeCH_Three) -7Cy], [4- (CCH_ThreeCH_ThreeCH_Three) -7Cy], [4- (CH₂CH₂CH₂CH₂CH_Three) -7Cy], [4- (CH₂CH₂CH₂CH₂CH₂CH_Three) -7Cy], [4- (CH₂CH₂CH₂CH₂CH₂CH₂CH_Three) -7Cy], [4-F-7Cy], [4- (OCH_Three) -7Cy], [4- (OCF_Three) -7Cy], [4- (CN) -7Cy], [4- (NMe₂) -7Cy], [4- (CF_Three) -7Cy], [4- (CH₂CF_Three) -7Cy], [4- (CH₂CH₂CF_Three) -7Cy], [4- (CH₂CH₂CH₂CF_Three) -7Cy], [4- (CH₂CH₂CH₂CH₂CF_Three) -7Cy], [4-Ph-7Cy], [4- (CH₂Ph) -7Cy], [4- (CH₂CH₂Ph) -7Cy], [4- (CH₂CH₂CH₂Ph) -7Cy], [4- (CH₂CH₂CH₂CH₂Ph) -7Cy], [4- (2-F-Ph) -7Cy], [4- (CH₂(4-F-Ph))-7Cy], [4- (CH₂CH₂(2- (Cl-Ph))-7Cy], [4- (CH₂CH₂CH₂(4-CF_Three-Ph))-7Cy], [4- (CH₂CH₂CH₂CH₂(4-OCF_Three-Ph))-7Cy], [4- (NA1) -7Cy], [4- (CH₂(NA1))-7Cy], [4- (CH₂CH₂(NA2))-7Cy], [4- (CH₂CH₂CH₂(NA2))-7Cy], [4- (8-F-NA2))-7Cy], [4- (CH₂CH₂OPh) -7Cy], [4- (CH₂CH₂CH₂CH₂CH₂OCH₂(NA2))-7Cy], (4- (CH₂CH₂(IN1))-7Cy], [4- (CH₂CH₂(IN2))-7Cy], [4- (CH₂CH₂(Py2))-7Cy], [4- (CH₂CH₂(Qun2))-7Cy], [4- (CH₂CH₂(Fur2))-7Cy], [4- (CH₂CH₂(Thi2))-7Cy], [4- (CH₂CH₂(BF5))-7Cy], [4- (CH₂CH₂(BF2))-7Cy], [4- (CH₂CH₂(BT5))-7Cy], [4- (CH₂CH₂(BT2))-7Cy], [4- (CH₂CH₂(BDXO5))-7Cy], [4- (CH₂CH₂(BDXA6))-7Cy], [4- (CH₂(4Cy))-7Cy], [4- (CH₂CH₂(5Cy))-7Cy] (4- (CH₂CH₂(2,2-F₂) -3Cy) -7Cy], [4- (CH₂CH₂(2- (CN) -3Cy))-7Cy], [4- (CH₂CH₂(2,2-F₂-BDXO5))-7Cy], [4- (IN1) -7Cy], [4- (Py2) -7Cy], [4- (Thi2) -7Cy], [4- (CH₂TN) -7Cy], [1-
(CH_Three) -3Cy], [1- (CN) -3Cy], [1- (CH_Three) -2- (CH_Three) -3Cy], [1- (CN) -2- (CH_Three) -3Cy], [1- (CH_Three) -2- (CH₂CH_Three) -3Cy], [1- (CN) -2- (CH₂CH_Three) -3Cy], [1- (CH_Three) -2-F-3Cy], [1- (CN) -2-F-3Cy], [1- (CH_Three) -2,2-F₂-3Cy], [1- (CN) -2,2-F₂-3Cy], [1- (CH_Three) -2-Ph-3Cy], [1- (CN) -2-Ph-3Cy], [1- (CH_Three) -2- (CH₂Ph) -3Cy], [1- (CN) -2- (CH₂Ph) -3Cy], [1- (CH_Three) -2- (CH₂CH₂Ph) -3Cy], [1- (CN) -2- (CH₂CH₂Ph) -3Cy], [1- (CH_Three) -2- (CH₂CH₂CH₂(4-CF_Three-Ph))-3Cy], [1- (CN) -2- (CH₂CH₂CH₂(4-CF_Three-Ph))-3Cy], [1- (CH_Three) -2- (CH₂CH₂CH₂CH₂(2- (NMe₂) Ph))-3Cy], (1- (CN) -2- (CH₂CH₂CH₂CH₂(2- (NMe₂) Ph))-3Cy], (1- (CH_Three) -2- (NA1) -3Cy], [1- (CN) -2- (NA1) -3Cy], [1- (CH_Three) -2- (CH₂(NA1))-3Cy], [1- (CN) -2- (CH₂(NA1))-3Cy], [1- (CH_Three) -2- (CH₂CH₂(NA1))-3Cy], [1- (CN) -2- (CH₂CH₂(NA1))-3Cy], [1- (CH_Three) -2- (NA2) -3Cy], [1- (CN) -2- (NA2) -3Cy], [1- (CH_Three) -2- (CH₂(NA2))-3Cy], [1- (CN) -2- (CH₂(NA2))-3Cy], [1- (CH_Three) -2- (CH₂CH₂(NA2))-3Cy], (1- (CN) -2- (CH₂CH₂(NA2))-3Cy], (1- (CH_Three) -2- (CH₂CH₂OPh) -3Cy], [1- (CN) -2- (CH₂CH₂OPh) -3Cy], [1- (CH_Three) -2- (CH₂CH₂(5Cy))-3Cy], (1- (CN) -2- (CH₂CH₂(5Cy))-3Cy], (1- (CH_Three) -2,2-Me₂-3Cy], [1- (CN) -2,2-Me₂-3Cy], [1- (CH_Three) -2,2-Me₂-3-Me-3Cy], [1- (CN) -2,2-Me₂-3-Me-3Cy], [1- (CH_Three) -2,2-Me₂-3,3-Me₂-3Cy], [1- (CN) -2,2-Me₂-3,3-Me₂-3Cy], [1- (CH_Three) -4Cy], [1- (CN) -4Cy], [1- (CH_Three) -2- (CH_Three) -4Cy], [1- (CN) -2- (CH_Three) -4Cy], [1- (CH_Three) -2- (CH₂CH_Three) -4Cy], [1- (CN) -2- (CH₂CH_Three) -4Cy], [1- (CH_Three) -2-F-4Cy], [1- (CN) -2-F-4Cy], [1- (CH_Three) -2,2-F₂-4Cy], [1- (CN) -2,2-F₂-4Cy], [1- (CH_Three) -2-Ph-4Cy], [1- (CN) -2-Ph-4Cy], [1- (CH_Three) -2- (CH₂Ph) -4Cy], [1- (CN) -2- (CH₂Ph) -4Cy], [1- (CH_Three) -2- (CH₂CH₂Ph) -4Cy], [1- (CN) -2- (CH₂CH₂Ph) -4Cy], [1- (CH_Three) -2- (CH₂CH₂CH₂(4-CF_Three-Ph))-4Cy], [1- (CN) -2- (CH₂CH₂CH₂(4-CF_Three-Ph))-4Cy], [1- (CH_Three) -2- (CH₂CH₂CH₂CH₂(2- (NMe₂) Ph))-4Cy], (1- (CN) -2- (CH₂CH₂CH₂CH₂(2- (NMe₂) Ph))-4Cy], (1- (CH_Three) -2- (NA1) -4Cy], [1- (CN) -2- (NA1) -4Cy], [1- (CH_Three) -2- (CH₂(NA1))-4Cy], [1- (CN) -2- (CH₂(NA1))-4Cy], [1- (CH_Three) -2- (CH₂CH₂(NA1))-4Cy], [1- (CN) -2- (CH₂CH₂(NA1))-4Cy], [1- (CH_Three) -2- (NA2) -4Cy], [1- (CN) -2- (NA2) -4Cy], [1- (CH_Three) -2- (CH₂(NA2))-4Cy], [1- (CN) -2- (CH₂(NA2))-4Cy], [1- (CH_Three) -2- (CH₂CH₂(NA2))-4Cy], (1- (CN) -2- (CH₂CH₂(NA2))-4Cy], (1- (CH_Three) -2- (CH₂CH₂OPh) -4Cy], [1- (CN) -2- (CH₂CH₂OPh) -4Cy], [1- (CH_Three) -2- (CH₂CH₂(5Cy))-4Cy], (1- (CN) -2- (CH₂CH₂(5Cy))-4Cy], (1- (CH_Three) -2,2-Me₂-4Cy], [1- (CN) -2,2-Me₂-4Cy], [1- (CH_Three) -2,2-Me₂-3-Me-4Cy], [1- (CN) -2,2-Me₂-3-Me-4Cy], [1- (CH_Three) -2,2-Me₂-3,3-Me₂-4Cy], [1- (CN) -2,2-Me₂-3,3-Me₂-4Cy], [1- (CH_Three) -3- (CH_Three) -4Cy], [1- (CN) -3- (CH_Three) -4Cy], [1- (CH_Three) -3- (CH₂CH_Three) -4Cy], [1- (CN) -3- (CH₂CH_Three) -4Cy], [1- (CH_Three) -3- (CH₂CH₂CH_Three) -4Cy], [1- (CN) -3- (CH₂CH₂CH_Three) -4Cy], [1- (CH_Three) -3-Ph-4Cy], [1- (CN) -3-Ph-4Cy], [1- (CH_Three) -3- (CH₂Ph) -4Cy], [1- (CN) -3- (CH₂Ph) -4Cy], [1- (CH_Three) -3- (CH₂CH₂Ph) -4Cy], [1- (CN) -3- (CH₂CH₂Ph) -4Cy], [1- (CH_Three) -3- (NA1) -4Cy], [1- (CN) -3- (NA1) -4Cy], [1- (CH_Three) -3- (CH₂(NA1))-4Cy], [1- (CN) -3- (CH₂(NA1))-4Cy], [1- (CH_Three) -3- (CH₂CH₂(NA1))-4Cy], [1- (CN) -3- (CH₂CH₂(NA1))-4Cy], [1- (CH_Three) -3- (NA2) -4Cy], [1- (CN) -3- (NA2) -4Cy], [1- (CH_Three) -3- (CH₂(NA2))-4Cy], [1- (CN) -3- (CH₂(NA2))-4Cy], [1- (CH_Three) -3- (CH₂CH₂(NA2))-4Cy], [1- (CN) -3- (CH₂CH₂(NA2))-4Cy], [1- (CH_Three) -3- (CH₂OPh) -4Cy], [1- (CN) -3- (CH₂OPh) -4Cy], [1- (CH_Three) -3- (CH₂CH₂O (NA1))-4Cy], [1- (CN) -3- (CH₂CH₂O (NA1))-4Cy], [1- (CH_Three) -3- (CH₂CH₂OCH₂(NA2))-4Cy], [1- (CN) -3- (CH₂CH₂OCH₂(NA2))-4Cy], [1- (CH_Three) -2-Me-3-Me-4Cy], [1- (CN) -2-Me-3-Me-4Cy], [1- (CH_Three) -5Cy], [1- (CN) -5Cy], [1- (CH_Three) -2- (CH_Three) -5Cy], [1- (CN) -2- (CH_Three) -5Cy], [1- (CH_Three) -2- (CH₂CH_Three) -5Cy], [1- (CN) -2- (CH₂CH_Three) -5Cy], [1- (CH_Three) -2-F-5Cy], [1- (CN) -2-F-5Cy], [1- (CH_Three) -2,2-F₂-5Cy], [1- (CN) -2,2-F₂-5Cy], [1- (CH_Three) -2-Ph-5Cy], [1- (CN) -2-Ph-5Cy], [1- (CH_Three) -2- (CH₂Ph) -5Cy], [1- (CN) -2- (CH₂Ph) -5Cy], [1- (CH_Three) -2- (CH₂CH₂Ph) -5Cy], [1- (CN) -2- (CH₂CH₂Ph) -5Cy], [1- (CH_Three) -2- (CH₂CH₂CH₂(4-CF_Three-Ph))-5Cy], [1- (CN) -2- (CH₂CH₂CH₂(4-CF_Three-Ph))-5Cy], [1- (CH_Three) -2- (CH₂CH₂CH₂CH₂(2- (NMe₂) Ph))-5Cy], (1- (CN) -2- (CH₂CH₂CH₂CH₂(2- (NMe₂) Ph))-5Cy], (1- (CH_Three) -2- (NA1) -5Cy], [1- (CN) -2- (NA1) -5Cy], [1- (CH_Three) -2- (CH₂(NA1))-5Cy], [1- (CN) -2- (CH₂(NA1))-5Cy], [1- (CH_Three) -2- (CH₂CH₂(NA1))-5Cy], [1- (CN) -2- (CH₂CH₂(NA1))-5Cy], [1- (CH_Three) -2- (NA2) -5Cy], [1- (CN) -2- (NA2) -5Cy], [1- (CH_Three) -2- (CH₂(NA2))-5Cy], [1- (CN) -2- (CH₂(NA2))-5Cy], [1- (CH_Three) -2- (CH₂CH₂(NA2))-5Cy], (1- (CN) -2- (CH₂CH₂(NA2))-5Cy], (1- (CH_Three) -2- (CH₂CH₂OPh) -5Cy], [1- (CN) -2- (CH₂CH₂OPh) -5Cy], [1- (CH_Three) -2- (CH₂CH₂(5Cy))-5Cy], (1- (CN) -2- (CH₂CH₂(5Cy))-5Cy], (1- (CH_Three) -2,2-Me₂-5Cy], [1- (CN) -2,2-Me₂-5Cy], [1- (CH_Three) -2,2-Me₂-3-Me-5Cy], [1- (CN) -2,2-Me₂-3-Me-5Cy], [1- (CH_Three) -2,2-Me₂-3,3-Me₂-5Cy], [1- (CN) -2,2-Me₂-3,3-Me₂-5Cy], [1- (CH_Three) -3- (CH_Three) -5Cy], [1- (CN) -3- (CH_Three) -5Cy], [1- (CH_Three) -3- (CH₂CH_Three) -5Cy], [1- (CN) -3- (CH₂CH_Three) -5Cy, [1- (CH_Three) -3- (CH₂CH₂CH_Three) -5Cy], [1- (CN) -3- (CH₂CH₂CH_Three) -5Cy], [1- (CH_Three) -3-Ph-5Cy], [1- (CN) -3-Ph-5Cy], [1- (CH_Three) -3- (CH₂Ph) -5Cy], [1- (CN) -3- (CH₂Ph) -5Cy], [1- (CH_Three) -3- (CH₂CH₂Ph) -5Cy], [1- (CN) -3- (CH₂CH₂Ph) -5Cy], [1- (CH_Three) -3- (NA1) -5Cy], [1- (CN) -3- (NA1) -5Cy], [1- (CH_Three) -3- (CH₂(NA1))-5Cy], [1- (CN) -3- (CH₂(NA1))-5Cy], [1- (CH_Three) -3- (CH₂CH₂(NA1))-5Cy], [1- (CN) -3- (CH₂CH₂(NA1))-5Cy], [1- (CH_Three) -3- (NA2) -5Cy], [1- (CN) -3- (NA2) -5Cy], [1- (CH_Three) -3- (CH₂(NA2))-5Cy], [1- (CN) -3- (CH₂(NA2))-5Cy], [1- (CH_Three) -3- (CH₂CH₂(NA2))-5Cy], [1- (CN) -3- (CH₂CH₂(NA2))-5Cy], [1- (CH_Three) -3- (CH₂OPh) -5Cy], [1- (CN) -3- (CH₂OPh) -5Cy], [1- (CH_Three) -3- (CH₂CH₂O (NA1))-5Cy], [1- (CN) -3- (CH₂CH₂O (NA1))-5Cy], [1- (CH_Three) -3- (CH₂CH₂OCH₂(NA2))-5Cy], [1- (CN) -3- (CH₂CH₂OCH₂(NA2))-5Cy], [1- (CH_Three) -2-Me-3-Me-5Cy], [1- (CN) -2-Me-3-Me-5Cy], [1- (CH_Three) -6Cy], [1- (CN) -6Cy], [1- (CH_Three) -2- (CH_Three) -6Cy], [1- (CN) -2- (CH_Three) -6Cy], [1- (CH_Three) -2- (CH₂CH_Three) -6Cy], [1- (CN) -2- (CH₂CH_Three) -6Cy], [1- (CH_Three) -2-F-6Cy], [1- (CN) -2-F-6Cy], [1- (CH_Three) -2,2-F₂-6Cy], [1- (CN) -2,2-F₂-6Cy], [1- (CH_Three) -2-Ph-6Cy], [1- (CN) -2-Ph-6Cy], [1- (CH_Three) -2- (CH₂Ph) -6Cy], [1- (CN) -2- (CH₂Ph) -6Cy], [1- (CH_Three) -2- (CH₂CH₂Ph) -6Cy], [1- (CN) -2- (CH₂CH₂Ph) -6Cy], [1- (CH_Three) -2- (CH₂CH₂CH₂(4-CF_Three-Ph))-6Cy], [1- (CN) -2- (CH₂CH₂CH₂(4-CF_Three-Ph))-6Cy], [1- (CH_Three) -2- (CH₂CH₂CH₂CH₂(2- (NMe
₂) Ph))-6Cy], (1- (CN) -2- (CH₂CH₂CH₂CH₂(2- (NMe₂) Ph))-6Cy], (1- (CH_Three) -2- (NA1) -6Cy], [1- (CN) -2- (NA1) -6Cy], [1- (CH_Three) -2- (CH₂(NA1))-6Cy], [1- (CN) -2- (CH₂(NA1))-6Cy], [1- (CH_Three) -2- (CH₂CH₂(NA1))-6Cy], [1- (CN) -2- (CH₂CH₂(NA1))-6Cy], [1- (CH_Three) -2- (NA2) -6Cy], [1- (CN) -2- (NA2) -6Cy], [1- (CH_Three) -2- (CH₂(NA2))-6Cy], [1- (CN) -2- (CH₂(NA2))-6Cy], [1- (CH_Three) -2- (CH₂CH₂(NA2))-6Cy], (1- (CN) -2- (CH₂CH₂(NA2))-6Cy], (1- (CH_Three) -2- (CH₂CH₂OPh) -6Cy], [1- (CN) -2- (CH₂CH₂OPh) -6Cy], [1- (CH_Three) -2- (CH₂CH₂(5Cy))-6Cy], (1- (CN) -2- (CH₂CH₂(5Cy))-6Cy], (1- (CH_Three) -2,2-Me₂-6Cy], [1- (CN) -2,2-Me₂-6Cy], [1- (CH_Three) -2,2-Me₂-3-Me-6Cy], [1- (CN) -2,2-Me₂-3-Me-6Cy], [1- (CH_Three) -2,2-Me₂-3,3-Me₂-6Cy], [1- (CN) -2,2-Me₂-3,3-Me₂-6Cy], [1- (CH_Three) -3- (CH_Three) -6Cy], [1- (CN) -3- (CH_Three) -6Cy], [1- (CH_Three) -3- (CH₂CH_Three) -6Cy], [1- (CN) -3- (CH₂CH_Three) -6Cy], [1- (CH_Three) -3- (CH₂CH₂CH_Three) -6Cy], [1- (CN) -3- (CH₂CH₂CH_Three) -6Cy], [1- (CH_Three) -3-Ph-6Cy], [1- (CN) -3-Ph-6Cy], [1- (CH_Three) -3- (CH₂Ph) -6Cy], [1- (CN) -3- (CH₂Ph) -6Cy], [1- (CH_Three) -3- (CH₂CH₂Ph) -6Cy], [1- (CN) -3- (CH₂CH₂Ph) -6Cy], [1- (CH_Three) -3- (NA1) -6Cy], [1- (CN) -3- (NA1) -6Cy], [1- (CH_Three) -3- (CH₂(NA1))-6Cy], [1- (CN) -3- (CH₂(NA1))-6Cy], [1- (CH_Three) -3- (CH₂CH₂(NA1))-6Cy], [1- (CN) -3- (CH₂CH₂(NA1))-6Cy], [1- (CH_Three) -3- (NA2) -6Cy], [1- (CN) -3- (NA2) -6Cy], [1- (CH_Three) -3- (CH₂(NA2))-6Cy], [1- (CN) -3- (CH₂(NA2))-6Cy], [1- (CH_Three) -3- (CH₂CH₂(NA2))-6Cy], [1- (CN) -3- (CH₂CH₂(NA2))-6Cy], [1- (CH_Three) -3- (CH₂OPh) -6Cy], [1- (CN) -3- (CH₂OPh) -6Cy], [1- (CH_Three) -3- (CH₂CH₂O (NA1))-6Cy], [1- (CN) -3- (CH₂CH₂O (NA1))-6Cy], [1- (CH_Three) -3- (CH₂CH₂OCH₂(NA2))-6Cy], [1- (CN) -3- (CH₂CH₂OCH₂(NA2))-6Cy], [1- (CH_Three) -2-Me-3-Me-6Cy], [1- (CN) -2-Me-3-Me-6Cy], [1- (CH_Three) -4- (CH_Three) -6Cy], [1- (CN) -4- (CH_Three) -6Cy], [1- (CH_Three) -4- (CH₂CH_Three) -6Cy], [1- (CN) -4- (CH₂CH_Three) -6Cy], [1- (CH_Three) -4- (CH₂CH₂CH_Three) -6Cy], [1- (CN) -4- (CH₂CH₂CH_Three) -6Cy], [1- (CH_Three) -4-Ph-6Cy], [1- (CN) -4-Ph-6Cy], [1- (CH_Three) -4- (CH₂Ph) -6Cy], [1- (CN) -4- (CH₂Ph) -6Cy], [1- (CH_Three) -4- (CH₂CH₂Ph) -6Cy], [1- (CN) -4- (CH₂CH₂Ph) -6Cy], [1- (CH_Three) -4- (NA1) -6Cy], [1- (CN) -4- (NA1) -6Cy], [1- (CH_Three) -4- (CH₂(NA1))-6Cy], [1- (CN) -4- (CH₂(NA1))-6Cy], [1- (CH_Three) -4- (CH₂CH₂(NA1))-6Cy], [1- (CN) -4- (CH₂CH₂(NA1))-6Cy], [1- (CH_Three) -4- (NA2) -6Cy], [1- (CN) -4- (NA2) -6Cy], [1- (CH_Three) -4- (CH₂(NA2))-6Cy], [1- (CN) -4- (CH₂(NA2))-6Cy], [1- (CH_Three) -4- (CH₂CH₂(NA2))-6Cy], [1- (CN) -4- (CH₂CH₂(NA2))-6Cy], [1- (CH_Three) -4- (CH₂OPh) -6Cy], [1- (CN) -4- (CH₂OPh) -6Cy], [1- (CH_Three) -4- (CH₂CH₂O (NA1))-6Cy], [1- (CN) -4- (CH₂CH₂O (NA1))-6Cy], [1- (CH_Three) -4- (CH₂CH₂OCH₂(NA2))-6Cy], [1- (CN) -4- (CH₂CH₂OCH₂(NA2))-6Cy], [1- (CH_Three) -3-Me-4-Me-6Cy], [1- (CN) -3-Me-4-Me-6Cy], [1- (CH_Three) -7Cy], [1- (CN) -7Cy], [1- (CH_Three) -2- (CH_Three) -7Cy], [1- (CN) -2- (CH_Three) -7Cy], [1- (CH_Three) -2- (CH₂CH_Three) -7Cy], [1- (CN) -2- (CH₂CH_Three) -7Cy], [1- (CH_Three) -2-F-7Cy], [1- (CN) -2-F-7Cy], [1- (CH_Three) -2,2-F₂-7Cy], [1- (CN) -2,2-F₂-7Cy], [1- (CH_Three) -2-Ph-7Cy], [1- (CN) -2-Ph-7Cy], [1- (CH_Three) -2- (CH₂Ph) -7Cy], [1- (CN) -2- (CH₂Ph) -7Cy], [1- (CH_Three) -2- (CH₂CH₂Ph) -7Cy], [1- (CN) -2- (CH₂CH₂Ph) -7Cy], [1- (CH_Three) -2- (CH₂CH₂CH₂(4-CF_Three-Ph))-7Cy], [1- (CN) -2- (CH₂CH₂CH₂(4-CF_Three-Ph))-7Cy], [1- (CH_Three) -2- (CH₂CH₂CH₂CH₂(2- (NMe₂) Ph))-7Cy], (1- (CN) -2- (CH₂CH₂CH₂CH₂(2- (NMe₂) Ph))-7Cy], (1- (CH_Three) -2- (NA1) -7Cy], [1- (CN) -2- (NA1) -7Cy], [1- (CH_Three) -2- (CH₂(NA1))-7Cy], [1- (CN) -2- (CH₂(NA1))-7Cy], [1- (CH_Three) -2- (CH₂CH₂(NA1))-7Cy], [1- (CN) -2- (CH₂CH₂(NA1))-7Cy], [1- (CH_Three) -2- (NA2) -7Cy], [1- (CN) -2- (NA2) -7Cy], [1- (CH_Three) -2- (CH₂(NA2))-7Cy], [1- (CN) -2- (CH₂(NA2))-7Cy], [1- (CH_Three) -2- (CH₂CH₂(NA2))-7Cy], (1- (CN) -2- (CH₂CH₂(NA2))-7Cy], (1- (CH_Three) -2- (CH₂CH₂OPh) -7Cy], [1- (CN) -2- (CH₂CH₂OPh) -7Cy], [1- (CH_Three) -2- (CH₂CH₂(5Cy))-7Cy], (1- (CN) -2- (CH₂CH₂(5Cy))-7Cy], (1- (CH_Three) -2,2-Me₂-7Cy], [1- (CN) -2,2-Me₂-7Cy], [1- (CH_Three) -2,2-Me₂-3-Me-7Cy], [1- (CN) -2,2-Me₂-3-Me-7Cy], [1- (CH_Three) -2,2-Me₂-3,3-Me₂-7Cy], [1- (CN) -2,2-Me₂-3,3-Me₂-7Cy], [1- (CH_Three) -3- (CH_Three) -7Cy], [1- (CN) -3- (CH_Three) -7Cy], [1- (CH_Three) -3- (CH₂CH_Three) -7Cy], [1- (CN) -3- (CH₂CH_Three) -7Cy], [1- (CH_Three) -3- (CH₂CH₂CH_Three) -7Cy], [1- (CN) -3- (CH₂CH₂CH_Three) -7Cy], [1- (CH_Three) -3-Ph-7Cy], [1- (CN) -3-Ph-7Cy], [1- (CH_Three) -3- (CH₂Ph) -7Cy], [1- (CN) -3- (CH₂Ph) -7Cy], [1- (CH_Three) -3- (CH₂CH₂Ph) -7Cy], [1- (CN) -3- (CH₂CH₂Ph) -7Cy], [1- (CH_Three) -3- (NA1) -7Cy], [1- (CN) -3- (NA1) -7Cy], [1- (CH_Three) -3- (CH₂(NA1))-7Cy], [1- (CN) -3- (CH₂(NA1))-7Cy], [1- (CH_Three) -3- (CH₂CH₂(NA1))-7Cy], [1- (CN) -3- (CH₂CH₂(NA1))-7Cy], [1- (CH_Three) -3- (NA2) -7Cy], [1- (CN) -3- (NA2) -7Cy], [1- (CH_Three) -3- (CH₂(NA2))-7Cy], [1- (CN) -3- (CH₂(NA2))-7Cy], [1- (CH_Three) -3- (CH₂CH₂(NA2))-7Cy], [1- (CN) -3- (CH₂CH₂(NA2))-7Cy], [1- (CH_Three) -3- (CH₂OPh) -7Cy], [1- (CN) -3- (CH₂OPh) -7Cy], [1- (CH_Three) -3- (CH₂CH₂O (NA1))-7Cy], [1- (CN) -3- (CH₂CH₂O (NA1))-7Cy], [1- (CH_Three) -3- (CH₂CH₂OCH₂(NA2))-7Cy], [1- (CN) -3- (CH₂CH₂OCH₂(NA2))-7Cy], [1- (CH_Three) -2-Me-3-Me-7Cy], [1- (CN) -2-Me-3-Me-7Cy], [1- (CH_Three) -4- (CH_Three) -7Cy], [1- (CN) -4- (CH_Three) -7Cy], [1- (CH_Three) -4- (CH₂CH_Three) -7Cy], [1- (CN) -4- (CH₂CH_Three) -7Cy], [1- (CH_Three) -4- (CH₂CH₂CH_Three) -7Cy], [1- (CN) -4- (CH₂CH₂CH_Three) -7Cy], [1- (CH_Three) -4-Ph-7Cy], [1- (CN) -4-Ph-7Cy], [1- (CH_Three) -4- (CH₂Ph) -7Cy], [1- (CN) -4- (CH₂Ph) -7Cy], [1- (CH_Three) -4- (CH₂CH₂Ph) -7Cy], [1- (CN) -4- (CH₂CH₂Ph) -7Cy], [1- (CH_Three) -4- (NA1) -7Cy], [1- (CN) -4- (NA1) -7Cy], [1- (CH_Three) -4- (CH₂(NA1))-7Cy], [1- (CN) -4- (CH₂(NA1))-7Cy], [1- (CH_Three) -4- (CH₂CH₂(NA1))-7Cy], [1- (CN) -4- (CH₂CH₂(NA1))-7Cy], [1- (CH_Three) -4- (NA2) -7Cy], [1- (CN) -4- (NA2) -7Cy], [1- (CH_Three) -4- (CH₂(NA2))-7Cy], [1- (CN) -4- (CH₂(NA2))-7Cy], [1- (CH_Three) -4- (CH₂CH₂(NA2))-7Cy], [1- (CN) -4- (CH₂CH₂(NA2))-7Cy], [1- (CH_Three) -4- (CH₂OPh) -7Cy], [1- (CN) -4- (CH₂OPh) -7Cy], [1- (CH_Three) -4- (CH₂CH₂O (NA1))-7Cy], [1- (CN) -4- (CH₂CH₂O (NA1))-7Cy], [1- (CH_Three) -4- (CH₂CH₂OCH₂(NA2))-7Cy], [1- (CN) -4- (CH₂CH₂OCH₂(NA2))-7Cy], [1- (CH_Three) -3-Me-4-Me-7Cy], [1- (CN) -3-Me-4-Me-7Cy]

本化合物Ａには、環構造、不斉炭素、又は硫黄原子に由来する異性体及びそれらの混合物も含まれる。例えば、式（Ｙ−１３１）で表される化合物においてＱ¹が〔2-(CH₂(2-F-Ph)-3Cy〕である化合物には１６個の異性体が存在する。異性体としては、例えば以下が挙げられる。

In the formula (Y-152), a compound in which Q ¹ is [3- (CH ₂ Ph) -4Cy] represents a compound in which Q ¹ is a 3-benzylcyclobutyl group in the formula (Y-152). Represents a compound represented by the following structural formula.

The compound A also includes isomers derived from a ring structure, asymmetric carbon, or a sulfur atom, and mixtures thereof. For example, in the compound represented by the formula (Y-131), the compound in which Q ¹ is [2- (CH ₂ (2-F-Ph) -3Cy] has 16 isomers. For example, the following may be mentioned.

A compound in which G ¹ is CPh also has a controlling effect on harmful arthropods. For example, in the compounds represented by formula (Y-1) to formula (Y-678), a compound in which Q ¹ is any group selected from the following group (Q-2) can be mentioned.

Group (Q-2)
[1-Ph-3Cy], [1-Ph-2- (CH ₃ ) -3Cy], [1-Ph-2- (CH ₂ CH ₃ ) -3Cy], [1-Ph-2-F-3Cy ], [1-Ph-2,2-F ₂ -3Cy], [1-Ph-2-Ph-3Cy], [1-Ph-2- (CH ₂ Ph) -3Cy], [1-Ph- 2- (CH ₂ CH ₂ Ph) -3Cy], [1-Ph-2- (CH ₂ CH ₂ CH ₂ (4-CF ₃ -Ph))-3Cy], [1-Ph-2- (CH ₂ CH ₂ CH ₂ CH ₂ (2- (NMe ₂ ) Ph))-3Cy], (1-Ph-2- (NA1) -3Cy), (1-Ph-2- (CH ₂ (NA1))-3Cy ], [1-Ph-2- (CH ₂ CH ₂ (NA1))-3Cy], [1-Ph-2- (NA2) -3Cy], [1-Ph-2- (CH ₂ (NA2)) -3Cy], [1-Ph-2- (CH ₂ CH ₂ (NA2))-3Cy], [1-Ph-2- (CH ₂ CH ₂ OPh) -3Cy], [1-Ph-2- ( CH ₂ CH ₂ (5Cy))-3Cy], (1-Ph-2,2-Me ₂ -3Cy), (1-Ph-2,2-Me ₂ -3-Me-3Cy), (1-Ph _{-2,2-Me 2 -3,3-Me 2} -3Cy ], [1-Ph-4Cy], _{[1-Ph-2- (CH 3} ) -4Cy ], [1-Ph-2- (CH ₂ CH ₃ ) -4Cy], [1-Ph-2-F-4Cy], [1-Ph-2,2-F ₂ -4Cy], [1-Ph-2-Ph-4Cy], [1- Ph-2- (CH ₂ Ph) -4Cy], [1-Ph-2- (CH ₂ CH ₂ Ph) -4Cy], [1-Ph-2- (CH ₂ CH ₂ CH ₂ (4-CF ₃ -Ph))-4Cy], [1-Ph-2- (CH ₂ CH ₂ CH ₂ CH ₂ (2- (NMe ₂ ) Ph))-4Cy], [1-Ph-2- (NA1) -4Cy ], [1-P h-2- (CH ₂ (NA1))-4Cy], [1-Ph-2- (CH ₂ CH ₂ (NA1))-4Cy], [1-Ph-2- (NA2) -4Cy], [ 1-Ph-2- (CH ₂ (NA2))-4Cy], [1-Ph-2- (CH ₂ CH ₂ (NA2))-4Cy], [1-Ph-2- (CH ₂ CH ₂ OPh ) -4Cy], [1-Ph-2- (CH ₂ CH ₂ (5Cy))-4Cy], [1-Ph-2,2-Me ₂ -4Cy], [1-Ph-2,2-Me ₂ -3-Me-4Cy], _{[1-Ph-2,2-Me 2} -3,3-Me 2 -4Cy ], _{[1-Ph-3- (CH 3} ) -4Cy ], [1-Ph -3- (CH ₂ CH ₃ ) -4Cy], [1-Ph-3- (CH ₂ CH ₂ CH ₃ ) -4Cy], [1-Ph-3-Ph-4Cy], [1-Ph-3 -(CH ₂ Ph) -4Cy], [1-Ph-3- (CH ₂ CH ₂ Ph) -4Cy], [1-Ph-3- (NA1) -4Cy], [1-Ph-3- ( CH ₂ (NA1))-4Cy], [1-Ph-3- (CH ₂ CH ₂ (NA1))-4Cy], [1-Ph-3- (NA2) -4Cy], [1-Ph-3 -(CH ₂ (NA2))-4Cy], [1-Ph-3- (CH ₂ CH ₂ (NA2))-4Cy], [1-Ph-3- (CH ₂ OPh) -4Cy], [1 -Ph-3- (CH ₂ CH ₂ O (NA1))-4Cy], [1-Ph-3- (CH ₂ CH ₂ OCH ₂ (NA2))-4Cy], [1-Ph-2-Me- 3-Me-4Cy], [1-Ph-5Cy], [1-Ph-2- (CH ₃ ) -5Cy], [1-Ph-2- (CH ₂ CH ₃ ) -5Cy], [1- Ph-2-F-5Cy], [1-Ph-2,2-F ₂ -5Cy], [1-Ph-2-Ph-5Cy], [1-Ph-2- (CH ₂ Ph) -5Cy ], [1-P h-2- (CH ₂ CH ₂ Ph) -5Cy], [1-Ph-2- (CH ₂ CH ₂ CH ₂ (4-CF ₃ -Ph))-5Cy], [1-Ph-2- ( CH ₂ CH ₂ CH ₂ CH ₂ (2- (NMe ₂ ) Ph))-5Cy], (1-Ph-2- (NA1) -5Cy), (1-Ph-2- (CH ₂ (NA1)) -5Cy], [1-Ph-2- (CH ₂ CH ₂ (NA1))-5Cy], [1-Ph-2- (NA2) -5Cy], [1-Ph-2- (CH ₂ (NA2 ))-5Cy], [1-Ph-2- (CH ₂ CH ₂ (NA2))-5Cy], [1-Ph-2- (CH ₂ CH ₂ OPh) -5Cy], [1-Ph-2 -(CH ₂ CH ₂ (5Cy))-5Cy], [1-Ph-2,2-Me ₂ -5Cy], [1-Ph-2,2-Me ₂ -3-Me-5Cy], [1 -Ph-2,2-Me ₂ -3,3-Me ₂ -5Cy], [1-Ph-3- (CH ₃ ) -5Cy], [1-Ph-3- (CH ₂ CH ₃ ) -5Cy ], [1-Ph-3- (CH ₂ CH ₂ CH ₃ ) -5Cy], [1-Ph-3-Ph-5Cy], [1-Ph-3- (CH ₂ Ph) -5Cy], [ 1-Ph-3- (CH ₂ CH ₂ Ph) -5Cy], [1-Ph-3- (NA1) -5Cy], [1-Ph-3- (CH ₂ (NA1))-5Cy], [ 1-Ph-3- (CH ₂ CH ₂ (NA1))-5Cy], [1-Ph-3- (NA2) -5Cy], [1-Ph-3- (CH ₂ (NA2))-5Cy] , [1-Ph-3- (CH ₂ CH ₂ (NA2))-5Cy], [1-Ph-3- (CH ₂ OPh) -5Cy], [1-Ph-3- (CH ₂ CH ₂ O (NA1))-5Cy], [1-Ph-3- (CH ₂ CH ₂ OCH ₂ (NA2))-5Cy], [1-Ph-2-Me-3-Me-5Cy], [1-Ph -6Cy], _{1-Ph-2- (CH 3} ) -6Cy ], _{[1-Ph-2- (CH 2} CH 3) -6Cy ], [1-Ph-2-F- 6Cy ], [1-Ph-2, 2-F ₂ -6Cy], [1-Ph-2-Ph-6Cy], [1-Ph-2- (CH ₂ Ph) -6Cy], [1-Ph-2- (CH ₂ CH ₂ Ph) -6Cy], [1-Ph-2- (CH ₂ CH ₂ CH ₂ (4-CF ₃ -Ph))-6Cy], [1-Ph-2- (CH ₂ CH ₂ CH ₂ CH ₂ (2- (NMe ₂ ) Ph))-6Cy], [1-Ph-2- (NA1) -6Cy], [1-Ph-2- (CH ₂ (NA1))-6Cy], [1-Ph-2- (CH ₂ CH ₂ (NA1))-6Cy], [1-Ph-2- (NA2) -6Cy], [1-Ph-2- (CH ₂ (NA2))-6Cy], [1-Ph- 2- (CH ₂ CH ₂ (NA2))-6Cy], [1-Ph-2- (CH ₂ CH ₂ OPh) -6Cy], [1-Ph-2- (CH ₂ CH ₂ (5Cy))- 6Cy], [[1-Ph-2,2-Me ₂ -6Cy], [1-Ph-2,2-Me ₂ -3-Me-6Cy], [1-Ph-2,2-Me _2- 3,3-Me ₂ -6Cy], [1-Ph-3- (CH ₃ ) -6Cy], [1-Ph-3- (CH ₂ CH ₃ ) -6Cy], [1-Ph-3- ( CH ₂ CH ₂ CH ₃ ) -6Cy], [1-Ph-3-Ph-6Cy], [1-Ph-3- (CH ₂ Ph) -6Cy], [1-Ph-3- (CH ₂ CH ₂ Ph) -6Cy], [1-Ph-3- (NA1) -6Cy], [1-Ph-3- (CH ₂ (NA1))-6Cy], [1-Ph-3- (CH ₂ CH ₂ (NA1))-6Cy], [1-Ph-3- (NA2) -6Cy], [1-Ph-3- (CH ₂ (NA2))-6Cy], [1-Ph-3- (CH ₂ CH ₂ (NA2 ))-6Cy], [1-Ph-3- (CH ₂ OPh) -6Cy], [1-Ph-3- (CH ₂ CH ₂ O (NA1))-6Cy], [1-Ph-3- (CH ₂ CH ₂ OCH ₂ (NA2))-6Cy], [1-Ph-2-Me-3-Me-6Cy], [1-Ph-4- (CH ₃ ) -6Cy], [1-Ph -4- (CH ₂ CH ₃ ) -6Cy], [1-Ph-4- (CH ₂ CH ₂ CH ₃ ) -6Cy], [1-Ph-4-Ph-6Cy], [1-Ph-4 -(CH ₂ Ph) -6Cy], [1-Ph-4- (CH ₂ CH ₂ Ph) -6Cy], [1-Ph-4- (NA1) -6Cy], [1-Ph-4- ( CH ₂ (NA1))-6Cy], [1-Ph-4- (CH ₂ CH ₂ (NA1))-6Cy], [1-Ph-4- (NA2) -6Cy], [1-Ph-4 -(CH ₂ (NA2))-6Cy], [1-Ph-4- (CH ₂ CH ₂ (NA2))-6Cy], [1-Ph-4- (CH ₂ OPh) -6Cy], [1 -Ph-4- (CH ₂ CH ₂ O (NA1))-6Cy], [1-Ph-4- (CH ₂ CH ₂ OCH ₂ (NA2))-6Cy], [1-Ph-3-Me- 4-Me-6Cy], [1-Ph-7Cy], [1-Ph-2- (CH ₃ ) -7Cy], [1-Ph-2- (CH ₂ CH ₃ ) -7Cy], [1- Ph-2-F-7Cy], [1-Ph-2,2-F ₂ -7Cy], [1-Ph-2-Ph-7Cy], [1-Ph-2- (CH ₂ Ph) -7Cy ], [1-Ph-2- (CH ₂ CH ₂ Ph) -7Cy], [1-Ph-2- (CH ₂ CH ₂ CH ₂ (4-CF ₃ -Ph))-7Cy], [1- Ph-2- (CH ₂ CH ₂ CH ₂ CH ₂ (2- (NMe ₂ ) Ph))-7Cy], [1-Ph-2- (NA1) -7Cy], [1-Ph-2- ( CH ₂ (NA1))-7Cy], [1-Ph-2- (CH ₂ CH ₂ (NA1))-7Cy], [1-Ph-2- (NA2) -7Cy], [1-Ph-2 -(CH ₂ (NA2))-7Cy], [1-Ph-2- (CH ₂ CH ₂ (NA2))-7Cy], [1-Ph-2- (CH ₂ CH ₂ OPh) -7Cy], (1-Ph-2- (CH ₂ CH ₂ (5Cy))-7Cy], (1-Ph-2,2-Me ₂ -7Cy), (1-Ph-2,2-Me ₂ -3-Me -7Cy], [1-Ph-2,2-Me ₂ -3,3-Me ₂ -7Cy], [1-Ph-3- (CH ₃ ) -7Cy], [1-Ph-3- (CH ₂ CH ₃ ) -7Cy], [1-Ph-3- (CH ₂ CH ₂ CH ₃ ) -7Cy], [1-Ph-3-Ph-7Cy], [1-Ph-3- (CH ₂ Ph ) -7Cy], [1-Ph-3- (CH ₂ CH ₂ Ph) -7Cy], [1-Ph-3- (NA1) -7Cy], [1-Ph-3- (CH ₂ (NA1) ) -7Cy], [1-Ph-3- (CH ₂ CH ₂ (NA1))-7Cy], [1-Ph-3- (NA2) -7Cy], [1-Ph-3- (CH ₂ ( NA2))-7Cy], [1-Ph-3- (CH ₂ CH ₂ (NA2))-7Cy], [1-Ph-3- (CH ₂ OPh) -7Cy], [1-Ph-3- (CH ₂ CH ₂ O (NA1))-7Cy], [1-Ph-3- (CH ₂ CH ₂ OCH ₂ (NA2))-7Cy], [1-Ph-2-Me-3-Me-7Cy ], [1-Ph-4- (CH ₃ ) -7Cy], [1-Ph-4- (CH ₂ CH ₃ ) -7Cy], [1-Ph-4- (CH ₂ CH ₂ CH ₃ )- 7Cy], [1-Ph-4-Ph-7Cy], [1-Ph-4- (CH ₂ Ph) -7Cy], [1-Ph-4- (CH ₂ CH ₂ Ph) -7Cy], [ 1 -Ph-4- (NA1) -7Cy], [1-Ph-4- (CH ₂ (NA1))-7Cy], [1-Ph-4- (CH ₂ CH ₂ (NA1))-7Cy], [1-Ph-4- (NA2) -7Cy], [1-Ph-4- (CH ₂ (NA2))-7Cy], [1-Ph-4- (CH ₂ CH ₂ (NA2))-7Cy ], [1-Ph-4- (CH ₂ OPh) -7Cy], [1-Ph-4- (CH ₂ CH ₂ O (NA1))-7Cy], [1-Ph-4- (CH ₂ CH ₂ OCH ₂ (NA2))-7Cy], [1-Ph-3-Me-4-Me-7Cy]

Next, formulation examples are shown. In addition, a part shows a weight part.
Formulation Example 1
10 parts of any one of the present compounds A are mixed in a mixture of 35 parts of xylene and 35 parts of DMF, and then 14 parts of polyoxyethylene styryl phenyl ether and 6 parts of calcium dodecylbenzenesulfonate are added and mixed to each. To obtain a formulation.

Formulation Example 2
4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, 20 parts of synthetic silicon hydroxide fine powder and 54 parts of diatomaceous earth are added, and 20 parts of any one of the present compound A is added and mixed to prepare each preparation. obtain.

Formulation Example 3
1 part of the synthetic silicon-containing fine powder, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65 parts of kaolin clay are mixed with 2 parts of any one of the present compounds A and mixed. Next, an appropriate amount of water is added to the mixture, and the mixture is further stirred, granulated by a granulator, and dried by ventilation to obtain each preparation.

Formulation Example 4
1 part of any one of the present compounds A is mixed with an appropriate amount of acetone, and 5 parts of a synthetic hydrous silicon oxide fine powder, 0.3 part of isopropyl acid phosphate and 93.7 parts of kaolin clay are added and sufficiently stirred. Mix and evaporate off the acetone to obtain each formulation.

Formulation Example 5
35 parts of a mixture of polyoxyethylene alkyl ether sulfate ammonium salt and white carbon (weight ratio 1: 1), 20 parts of any one of the present compound A, and 45 parts of water are sufficiently mixed to obtain a preparation.

Formulation Example 6
After mixing 10 parts of any one of the present compounds A and 10 parts of phenylxylylethane, the resulting mixture was added to 20 parts of a 10% aqueous solution of polyethylene glycol and stirred with a homomixer to obtain an average particle size. A 3 μm emulsion is obtained. On the other hand, 0.2 parts of xanthan gum and 1.0 part of aluminum magnesium silicate are dispersed in 58.8 parts of ion-exchanged water to obtain a thickener solution. 40 parts of the emulsion solution and 60 parts of the thickener solution are mixed to obtain a preparation.

Formulation Example 7
0.1 part of any one of the present compound A is added to 10 parts of isopropyl alcohol, and this is mixed with 89.9 parts of kerosene to obtain a preparation.

Formulation Example 8
Put 0.1 part of this compound A and 49.9 parts of kerosene into an aerosol can, attach an aerosol valve, fill 25 parts of dimethyl ether and 25 parts of LPG, shake, and attach an actuator. To obtain an oil aerosol.

Formulation Example 9
0.6 part of any one of the present compounds A, 0.01 part of 2,6-di-tert-butyl-4-methylphenol, 5 parts of xylene, 3.39 parts of kerosene and an emulsifier {Rheodor MO-60 (Kao (Made by Co., Ltd.)} A mixture of 1 part and 50 parts of distilled water are filled in an aerosol container, and after mounting a valve, 40 parts of a propellant (LPG) is pressurized and charged through the valve to form an aqueous aerosol. obtain.

Formulation Example 10
0.3 g of any one of the present compounds A is made 20 mL of acetone, and this is uniformly mixed with an incense base material (tab powder: cocoon powder: wood powder = 4: 3: 3) 99.7 g After stirring and mixing, 100 mL of water is added, and the kneaded mixture is molded and dried to obtain an insecticidal incense.

Formulation Example 11
Acetone is added to 0.8 g of any one of the present compounds A and 0.4 g of piperonyl butoxide to make a total of 10 mL. 0.5 mL of this solution was uniformly impregnated into a 2.5 cm × 1.5 cm, 0.3 cm thick electric insecticidal mat substrate (a mixture of cotton linter and pulp filled into a plate). Get an electric insecticidal matting agent.

Formulation Example 12
3 parts of any one of the present compound A is added to 97 parts of kerosene to obtain a liquid agent, which is put in a vinyl chloride container so that the upper part can be heated with a heater (inorganic powder is hardened with a binder, By inserting the sintered), parts used for the liquid absorption core type heat transpiration apparatus are obtained.

Formulation Example 13
100 mg of any one of the present compounds A is dissolved in an appropriate amount of acetone and impregnated into a porous ceramic plate having a size of 4.0 cm × 4.0 cm and a thickness of 1.2 cm to obtain a heated smoke.

Formulation Example 14
One 100 μg of Compound A is dissolved in an appropriate amount of acetone, and uniformly applied to a filter paper having a size of 2 cm × 2 cm and a thickness of 0.3 mm, and then acetone is air-dried to obtain a room temperature volatilizer.

  Next, the harmful arthropod controlling effect of this compound is shown as a test example.

Test example 1
The test compound is diluted with a mixture of isopropyl alcohol / kerosene = 1/9 to obtain a diluted solution containing the test compound at a predetermined concentration.
Release 10 adult mosquitoes in a plastic cup (bottom diameter 10.6 cm) and cover with a net. The cup is placed on the inner bottom of the chamber (bottom: 46 cm × 46 cm, height: 70 cm). Spray 0.5 ml of the diluent from a height of 30 cm above the upper surface of the cup using a spray gun (spray pressure 0.4 kg / cm ² ). Immediately after spraying, the cup is removed from the chamber and the number of insects knocked down after 15 minutes is counted to determine the knockdown rate. The knockdown rate is calculated by the following formula.
Knockdown rate (%) = (number of knockdown insects / number of test insects) × 100

The test was conducted according to Test Example 1 using the following present compound as a test compound at a predetermined concentration of 0.5% w / v. As a result, all the compounds had a knockdown rate of 80% or more.
This compound: 14, 15, 16, 19, 32, 33, 35, 41 and 44

The test was conducted according to Test Example 1 using the following present compound as a test compound at a predetermined concentration of 0.1% w / v. As a result, all the compounds had a knockdown rate of 80% or more.
This compound: 1, 2, 3, 5, 6, 7, 8, 9, 13, 15, 16, and 32

で示される化合物（国際公開第２０１４／１１９６９６号に記載）を用いて試験例１に従って試験を行った。その結果、式（Ｘ）で示される化合物はノックダウン率が２０％以下であった。 Comparative Example 1
The predetermined concentration is 0.1% w / v, and the compound of formula (X)

Was tested according to Test Example 1 using the compound represented by the formula (described in International Publication No. 2014/119696). As a result, the compound represented by the formula (X) had a knockdown rate of 20% or less.

Test example 2
The test compound is diluted with a mixture of isopropyl alcohol / kerosene = 1/9 to obtain a diluted solution containing the test compound at a predetermined concentration.
Release 10 adult house flies (5 males and 5 5 females) into a plastic cup (bottom diameter 10.6 cm) and cover with a net. The cup is placed on the inner bottom of the chamber (bottom: 46 cm × 46 cm, height: 70 cm). Spray 0.5 ml of the diluted solution from a height of 30 cm above the upper surface of the cup using a spray gun (spray pressure 0.4 kg / cm ² ). Immediately after spraying, the cup is removed from the chamber and the number of insects knocked down after 15 minutes is counted to determine the knockdown rate. The knockdown rate is calculated by the following formula.
Knockdown rate (%) = (number of knockdown insects / number of test insects) × 100

The test was performed according to Test Example 2 using the following present compound as a test compound at a predetermined concentration of 0.5% w / v. As a result, all the compounds had a knockdown rate of 80% or more.
This compound: 5, 6 and 8

Test example 3
The test compound is diluted with a mixture of isopropyl alcohol / kerosene = 1/9 to obtain a diluted solution containing the test compound at a predetermined concentration.
10 German cockroaches (5 males and 5 females) are released in a container with a buttered inner wall (diameter: 8.75 cm, height: 7.5 cm, bottom 16 mesh wire mesh), and chamber (bottom: 46 cm x 46 cm, height: 70 cm) on the inner bottom. Spray 1.5 ml of the diluted solution from a height of 60 cm above the upper surface of the container using a spray gun (spray pressure 0.42 kg / cm ² ). Immediately after spraying, the cup is removed from the chamber and the number of insects knocked down after 15 minutes is counted to determine the knockdown rate. The knockdown rate is calculated by the following formula.
Knockdown rate (%) = (number of knockdown insects / number of test insects) × 100

The test was conducted according to Test Example 3 using the following present compound as a test compound at a predetermined concentration of 0.5% w / v. As a result, all the compounds had a knockdown rate of 80% or more.
This compound: 5 and 6

Test example 4
A test compound is prepared according to the method described in Formulation Example 5, water is added thereto, and a diluted solution containing the test compound at a predetermined concentration is prepared.
30 larvae of Culex pipiens larvae are released into the diluted solution, and after 1 day, the life and death are examined to determine the mortality rate. The death rate is calculated by the following formula.
Death rate (%) = (Number of dead insects / number of test insects) × 100

The test was performed according to Test Example 4 using the following concentration as a test compound at a predetermined concentration of 3.5 ppm. As a result, all compounds showed a death rate of 91% or more.
This compound: 2 and 3

Test Example 5
A test compound is prepared according to the method described in Formulation Example 5, and water is added thereto to prepare a diluted solution containing this compound at a predetermined concentration.
A filter paper of the same size is laid on the inner bottom of a 5.5 cm diameter container, 0.7 mL of the diluted solution is dropped on the filter paper, and 30 mg of sucrose is uniformly placed in the container as food. Release 10 adult houseflies into the container and cap. After 24 hours, the life of the house fly is examined to determine the death rate. The death rate is calculated by the following formula.
Death rate (%) = (Number of dead insects / number of test insects) × 100

Test Example 6
A test compound is prepared according to the method described in Formulation Example 5, and water is added thereto to prepare a diluted solution containing this compound at a predetermined concentration.
A filter paper of the same size is laid on the inner bottom of a 5.5 cm diameter container, 0.7 ml of the diluted solution is dropped on the filter paper, and 30 mg of sucrose is uniformly placed in the container as food. Release 2 adult German cockroaches into the container and cap. Six days later, the death and death of German cockroaches are investigated, the number of dead insects is counted, and the death rate is obtained by the following formula.
Death rate (%) = (Number of dead insects / number of test insects) × 100

Test Example 7
A test compound is prepared according to the method described in Formulation Example 5, and water containing 0.03% by volume of a spreading agent is added thereto to prepare a diluted solution containing the present compound at a predetermined concentration.
About 30 cotton aphids (all stages) are inoculated on Cucumber sativas seedlings (second true leaf development stage) planted in a container. One day later, the diluted solution is sprayed on the seedlings at a rate of 10 mL / seedling. After 5 days, the number of live insects is examined, and the control value is obtained 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 test insects in the untreated group Cai: Number of live insects at the time of survey in the untreated group Tb: Number of test insects in the treated group Tai: Number of live insects at the time of survey in the treated group It means a group that performs the same operation as the treatment group except that this compound is not used.

Test Example 8
A test compound is prepared according to the method described in Formulation Example 5, and water containing 0.03% by volume of a spreading agent is added thereto to prepare a diluted solution containing the present compound at a predetermined concentration.
The diluted solution is sprayed at a rate of 10 mL / seedling on rice (Oryza sativa) seedlings (second leaf development stage) planted in a container. Then, 20 3rd instar larvae are released. After 6 days, the number of surviving insects is examined, and the death rate is obtained by the following formula.
Death rate (%) = {1−number of surviving insects / 20} × 100

Test Example 9
A test compound is prepared according to the method described in Formulation Example 5, and water is added thereto to prepare a diluted solution containing this compound at a predetermined concentration.
5 mL of the diluent is added to a container, and rice seedlings (second leaf development stage) planted in a container having a hole in the bottom are accommodated therein. Seven days later, 20 third-instar larvae are released. Further, after 6 days, the number of surviving insects is investigated, and the death rate is obtained by the following formula.
Death rate (%) = {1−number of surviving insects / 20} × 100

Test Example 10
A test compound is prepared according to the method described in Formulation Example 5, and water is added thereto to prepare a diluted solution containing this compound at a predetermined concentration.
7.7 g of artificial feed (Insector LF, Nippon Agricultural Industry) is placed in a container, and 2 mL of the diluted solution is irrigated thereto. Release 5 4th instar larvae on the artificial feed. After 5 days, the number of live insects is counted and the mortality rate is obtained from the following formula.
Mortality (%) = (1−number of surviving insects / 5) × 100

Test Example 11
A test compound is prepared according to the method described in Formulation Example 5, and water containing 0.03% by volume of a spreading agent is added thereto to prepare a diluted solution containing the present compound at a predetermined concentration.
The diluted solution is sprayed on a cabbage (Brassicae oleracea) seedling (second to third true leaf development stage) planted in a container at a rate of 20 mL / seedling. Thereafter, the stems and leaves of this seedling are cut out and placed in a container with filter paper. Release 5 5th instar larvae. Five days later, the number of live insects is counted, and the death rate is obtained from the following formula.
Death rate% = (1−Number of surviving insects / 5) × 100

The composition of the present invention has excellent control activity against harmful arthropods.

Claims (4)

Formula (I)

[Where,
R ¹ is a C1-C8 chain hydrocarbon group which may have one or more substituents selected from group A1, and a C3-C7 cycloalkyl which may have one or more substituents selected from group A2. A group, a phenyl group optionally having one or more substituents selected from group A2, a 5-10 membered heteroaryl group optionally having one or more substituents selected from group A2, or a group B Represents a 3- to 7-membered saturated heterocyclic group optionally having one or more substituents,
G ¹ represents CH, C (CH ₃ ), or C (CN);
G ² represents CR ² R ³ ,
G ³ represents a single bond or CR ⁴ R ⁵ ,
G ⁴ represents a single bond or CR ⁶ R ⁷ ,
G ⁵ represents a single bond or CR ⁸ R ⁹ ;
G ⁶ represents a single bond or CR ¹⁰ R ¹¹ ,
G ⁷ represents CR ¹² R ¹³ ,
R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ , R ¹² , and R ¹³ are each independently a halogen atom, nitro group, cyano Group, formyl group, NR ¹⁸ R ¹⁹ {R ¹⁸ and R ¹⁹ each independently represents a C1-C6 alkyl group optionally having one or more halogen atoms or a hydrogen atom}, selected from group C A C1-C8 chain hydrocarbon group optionally having one or more substituents, a C1-C4 alkoxy group optionally having one or more substituents selected from group C, one or more selected from group D A C6-C10 aryl group optionally having substituent (s), a C6-C10 aryloxy group optionally having one or more substituents selected from group D, and one or more substituents selected from group D An optionally substituted 5-10 membered heteroaryl group, optionally having one or more substituents selected from group D Black represents an alkyl group or a hydrogen atom,
X represents a hydrogen atom, a halogen atom, a C1-C3 chain hydrocarbon group, a cyano group, a formyl group, a hydroxy group, or a C1-C3 alkoxy group.
Group A1: A C3-C7 cycloalkyl group optionally having one or more substituents selected from Group A2, a phenyl group optionally having one or more substituents selected from Group A2, and a group A2 5-10 membered heteroaryl group optionally having one or more substituents, 3-7 membered saturated heterocyclic group optionally having one or more substituents from group B, halogen atom, one or more halogens A group consisting of a C1-C4 alkoxy group optionally having an atom, a hydroxy group, a C2-C5 alkoxycarbonyl group optionally having one or more halogen atoms, NR ¹⁴ R ¹⁵ and C (O) NR ¹⁴ R ¹⁵ {R ¹⁴ and R ¹⁵ each independently represents a C1-C6 alkyl group which may have one or more halogen atoms or a hydrogen atom}.
Group A2: halogen atom, C1-C4 alkyl group optionally having one or more halogen atoms, C1-C4 alkoxy group optionally having one or more halogen atoms, hydroxy group, nitro group, cyano group, formyl Group, C2-C5 alkoxycarbonyl group optionally having one or more halogen atoms, a group consisting of NR ¹⁶ R ¹⁷ and C (O) NR ¹⁶ R ¹⁷ {R ¹⁶ and R ¹⁷ are each independently 1 Represents a C1-C6 alkyl group or a hydrogen atom which may have the above halogen atoms}.
Group B: C1-C4 alkyl group which may have one or more halogen atoms, C1-C4 alkoxy group which may have one or more halogen atoms, C2- which may have one or more halogen atoms A group consisting of a C5 alkoxycarbonyl group, an oxo group and a halogen atom.
Group C: C3-C7 cycloalkyl group optionally having one or more substituents selected from Group D, C6-C10 aryl group optionally having one or more substituents selected from Group D, Group D A C6-C10 aryloxy group optionally having one or more substituents selected from the above, a (C6-C10 aryl) C1-C4 alkoxy group optionally having one or more substituents selected from the group D, a group 5-10 membered heteroaryl group optionally having one or more substituents selected from D, C1-C4 alkoxy group optionally having one or more halogen atoms, halogen atom, hydroxy group, nitro group, cyano A group consisting of a group, a formyl group, a C2-C5 alkoxycarbonyl group optionally having one or more halogen atoms, NR ¹⁸ R ¹⁹ and C (O) NR ¹⁸ R ¹⁹ .
Group D: C1-C4 chain hydrocarbon group which may have one or more halogen atoms, C1-C4 alkoxy group which may have one or more halogen atoms, or one or more halogen atoms Good C1-C4 alkoxyalkyl group, C1-C4 alkylthio group optionally having one or more halogen atoms, C1-C4 alkylsulfinyl group optionally having one or more halogen atoms, having one or more halogen atoms C1-C4 alkylsulfonyl group which may have one or more, C2-C5 alkoxycarbonyl group which may have one or more halogen atoms, hydroxy group, nitro group, cyano group, formyl group, carboxy group, NR ²⁰ R ²¹ , CONR ²⁰ R ²¹ and the group {R ²⁰ and R ²¹ consisting of a halogen atom, each independently, 1 or more halogen atoms or C1-C6 alkyl group or a hydrogen atom may have a Be}]
A harmful arthropod control composition comprising a compound represented by the above or a salt thereof and an inert carrier. R ¹ is a C1-C6 chain hydrocarbon group that may have one or more substituents selected from group A3, a C3-C6 cycloalkyl group that may have a hydroxy group, a phenyl group, a pyridyl group { The phenyl group and the pyridyl group may have one or more substituents selected from the group consisting of a halogen atom and a C1-C4 alkyl group}, an azetidinyl group, a pyrrolidinyl group, or a piperidyl group {the azetidinyl group, The pyrrolidinyl group and the piperidyl group are selected from the group consisting of a C1-C4 alkyl group which may have one or more halogen atoms and a C2-C5 alkoxycarbonyl group which may have one or more halogen atoms. Which may have one or more substituents}
G ¹ is CH,
R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ , R ¹² , and R ¹³ are each independently one or more selected from group F A phenyl group which may have one of the substituents, a naphthyl group which may have one or more substituents selected from group F, and a C1-C2 which may have one or more substituents selected from group G A chain hydrocarbon group or a hydrogen atom,
The harmful arthropod control composition according to claim 1, wherein X is a hydrogen atom.
Group A3: selected from methoxy group, amino group, methylamino group, dimethylamino group, tetrahydrofuranyl group, tetrahydropyranyl group, phenyl group optionally having one or more substituents selected from group F, and group F A group consisting of a pyridyl group optionally having one or more substituents.
Group F: Group consisting of halogen atom, methyl group, trifluoromethyl group, methoxy group, trifluoromethoxy group, hydroxy group, amino group, methylamino group, dimethylamino group, nitro group, cyano group, and formyl group.
Group G: A group consisting of a phenyl group which may have one or more substituents selected from Group F and a naphthyl group which may have one or more substituents selected from Group F.   A method for controlling harmful arthropods, which comprises applying the composition for controlling harmful arthropods according to claim 1 or 2 to harmful arthropods or habitats of harmful arthropods. Formula (II)

[Where,
R ^1x is a C1-C6 chain hydrocarbon group that may have one or more substituents selected from group A3, a C3-C6 cycloalkyl group that may have a hydroxy group, a phenyl group, or a pyridyl group. {The phenyl group and the pyridyl group may have one or more halogen atoms or methyl groups};
G ^2x represents CR ^2x R ^3x
G ^3x represents a single bond or CR ^4x R ^5x ,
G ^4x represents a single bond or CR ^6x R ^7x ,
G ^5x represents a single bond or CR ^8x R ^9x ,
G ^6x represents a single bond or CR ^10x R ^11x ,
G ^7x represents CR ^12x R ^13x
R ^2x , R ^3x , R ^4x , R ^5x , R ^6x , R ^7x , R ^8x , R ^9x , R ^10x , R ^11x , R ^12x , and R ^13x are each independently one or more selected from group F A phenyl group which may have one of the substituents, a naphthyl group which may have one or more substituents selected from group F, and a C1-C2 which may have one or more substituents selected from group G Represents a chain hydrocarbon group or a hydrogen atom.
Group A3: selected from methoxy group, amino group, methylamino group, dimethylamino group, tetrahydrofuranyl group, tetrahydropyranyl group, phenyl group optionally having one or more substituents selected from group F, and group F A group consisting of a pyridyl group optionally having one or more substituents.
Group F: Group consisting of halogen atom, methyl group, trifluoromethyl group, methoxy group, trifluoromethoxy group, hydroxy group, amino group, methylamino group, dimethylamino group, nitro group, cyano group, formyl group.
Group G: A group consisting of a phenyl group which may have one or more substituents selected from Group F and a naphthyl group which may have one or more substituents selected from Group F. ]
Or a salt thereof.