JP2009215230A - Thiadiazole compound, and use thereof - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a compound having excellent efficacy in controlling harmful arthropods. <P>SOLUTION: Disclosed is a thiadiazole compound represented by formula (I). In the formula, R represents a 1-7C linear hydrocarbon group (provided that the linear hydrocarbon group may be substituted with one or more of substituents selected from the group consisting of halogen atoms or the like), a 3 to 10 membered carbocyclic group (provided that the carbocyclic group may be substituted with one or more of substituents selected from the group consisting of halogen atoms or the like), or a 3 to 10 membered heterocyclic group (provided that the heterocycle group may be substituted with one or more of substituents selected from the group consisting of halogen atoms or the like). <P>COPYRIGHT: (C)2009,JPO&INPIT

Description

  The present invention relates to thiadiazole compounds and their use for controlling harmful arthropods.

  Conventionally, many compounds have been developed as active ingredients of pest control agents and put into practical use. In addition, it is known that certain thiadiazole compounds have a controlling effect on harmful arthropods (see, for example, Patent Document 1 and Patent Document 2).

DE3030661 JP 2003-277372 A

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

  As a result of intensive studies to find a compound having an excellent harmful arthropod controlling effect, the present inventor found that the thiadiazole compound represented by the following formula (I) has an excellent harmful arthropod controlling effect, Completed the invention.

〔式中、
ＲはＣ１−Ｃ７鎖式炭化水素基（但し、該鎖式炭化水素基は下記Ａ群より選ばれる１以上の置換基で置換されていてもよい。）、Ｃ３−Ｃ６アルカノイル基、-Ｑ基、-Ｔ-Ｑ基、-Ｔ-Ｏ-Ｑ基、または、-Ｔ-Ｏ-Ｔ-Ｑ基を表し、
Ｑは３〜１０員の炭素環基（但し、該炭素環基は下記Ｂ群より選ばれる１以上の置換基で置換されていてもよく、下記Ｃ群より選ばれる１以上の置換基で置換されていてもよい。）、または、３〜１０員の複素環基（但し、該複素環基は下記Ｂ群より選ばれる１以上の置換基で置換されていてもよく、下記Ｃ群より選ばれる１以上の置換基で置換されていてもよい。）を表し、
ＴはＣ１−Ｃ４アルカンジイル基をし、
Ａ群はハロゲン原子、シアノ基、ニトロ基、-Ｚ²-(Ｔ-Ｚ²)r-Ｒ¹⁰基、-(Ｚ²)p-Ｃ(=Ｏ)-(Ｚ³)q-Ｒ¹⁰基、および、-Ｃ(=ＮＯ-Ｒ¹⁰)-Ｒ¹¹基からなる１価の置換基の群を表し、
Ｂ群はハロゲン原子、シアノ基、ニトロ基、-Ｒ¹²基、-Ｚ²-(Ｔ-Ｚ²)r-Ｒ¹⁰基、-(Ｔ-Ｚ²)s-Ｒ¹⁰基、-(Ｚ²)p-Ｃ(=Ｏ)-(Ｚ³)q-Ｒ¹⁰基、-Ｃ(=ＮＯ-Ｒ¹⁰)-Ｒ¹¹基、-Ｑ¹基、-Ｚ²-Ｑ¹基、-Ｔ-Ｑ¹基、-Ｚ²-Ｔ-Ｑ¹基、および、-Ｔ-Ｚ²-Ｑ¹基からなる１価の置換基の群を表し、
Ｃ群は酸素原子、硫黄原子、-Ｔ-基、-Ｚ⁴-Ｔ-Ｚ⁵-基、および、-Ｔ-Ｚ⁴-Ｔ-基からなる２価の置換基の群を表す
｛ここで、
ｒは０、１または２を表し、ｐおよびｑは各々独立して０または１を表し、ｓは１または２を表し、
Ｚ²およびＺ³は各々独立して、酸素原子、硫黄原子、-ＮＨ-基または-Ｎ(Ｃ１−Ｃ６アルキル)-基を表し、
Ｚ⁴およびＺ⁵は各々独立して、酸素原子または硫黄原子を表し、
Ｒ¹⁰およびＲ¹¹は各々独立して、ハロゲン原子で置換されていてもよいＣ１−Ｃ７鎖式炭化水素基、または、水素原子を表し
Ｒ¹²はハロゲン原子で置換されていてもよいＣ１−Ｃ７鎖式炭化水素基を表し、
Ｑ¹は３〜１０員の炭素環基（但し、該炭素環基は上記Ａ群より選ばれる１以上の置換基で置換されていてもよく、同一または隣接する環構成原子上にて上記Ｃ群より選ばれる１以上の置換基で置換されていてもよい。）、または、３〜１０員の複素環基（但し、該複素環基は上記Ａ群より選ばれる１以上の置換基で置換されていてもよく、同一または隣接する環構成原子上にて上記Ｃ群より選ばれる１以上の２価の置換基で置換されていてもよい。）を表す。｝。〕
で示されるチアジアゾール化合物（以下、本発明化合物と記す。）、本発明化合物を有効成分として含有することを特徴とする有害節足動物防除剤、および、本発明化合物の有効量を有害節足動物または有害節足動物の生息場所に施用することを特徴とする有害節足動物の防除方法を提供する。 That is, the present invention provides a compound of formula (I)

[Where,
R is a C1-C7 chain hydrocarbon group (provided that the chain hydrocarbon group may be substituted with one or more substituents selected from the following group A), a C3-C6 alkanoyl group, a -Q group , -TQ group, -T-O-Q group, or -T-O-TQ group,
Q is a 3- to 10-membered carbocyclic group (provided that the carbocyclic group may be substituted with one or more substituents selected from the following group B, and substituted with one or more substituents selected from the following group C) Or a 3- to 10-membered heterocyclic group (provided that the heterocyclic group may be substituted with one or more substituents selected from the following group B and selected from the following group C) And may be substituted with one or more substituents.
T represents a C1-C4 alkanediyl group;
A group halogen atom, a cyano group, a nitro ^{group, -Z 2 - (T-Z} 2) r-R 10 ^{group, - (Z 2) p-} C (= O) - (Z 3) q-R 10 group And a group of monovalent substituents consisting of —C (═NO—R ¹⁰ ) —R ¹¹ groups,
Group B is a halogen atom, a cyano group, a nitro group, -R ^{12 group, -Z 2 - (T-Z} 2) r-R 10 ^{group, - (T-Z 2)} s-R 10 group, - (Z ² ) p-C (= O)-(Z ³ ) q-R ¹⁰ group, -C (= NO-R ¹⁰ ) -R ¹¹ group, -Q ¹ group, -Z ² -Q ¹ group, -TQ ¹ represents a group of monovalent substituents consisting of ¹ group, -Z ² -TQ ¹ group, and -TZ ² -Q ¹ group,
Group C represents a group of divalent substituents consisting of an oxygen atom, a sulfur atom, a -T- group, a -Z ⁴ -TZ ⁵ -group, and a -TZ ⁴ -T- group {here ,
r represents 0, 1 or 2, p and q each independently represents 0 or 1, s represents 1 or 2,
Z ² and Z ³ each independently represent an oxygen atom, a sulfur atom, a —NH— group or a —N (C 1 -C 6 alkyl) -group;
Z ⁴ and Z ⁵ each independently represents an oxygen atom or a sulfur atom,
R ¹⁰ and R ¹¹ each independently represent a C1-C7 chain hydrocarbon group which may be substituted with a halogen atom, or a hydrogen atom, and R ¹² may be substituted with a halogen atom. Represents a chain hydrocarbon group,
Q ¹ is a 3- to 10-membered carbocyclic group (provided that the carbocyclic group may be substituted with one or more substituents selected from Group A above, and the above C Substituted with one or more substituents selected from the group), or a 3- to 10-membered heterocyclic group (provided that the heterocyclic group is substituted with one or more substituents selected from Group A above) Which may be substituted with one or more divalent substituents selected from the group C on the same or adjacent ring constituent atoms. }. ]
A thiadiazole compound (hereinafter referred to as the compound of the present invention), an arthropod pesticide characterized by containing the compound of the present invention as an active ingredient, and an effective amount of the compound of the present invention in a harmful arthropod Alternatively, the present invention provides a method for controlling harmful arthropods, which is applied to a habitat of harmful arthropods.

  The compound of the present invention has an excellent harmful arthropod controlling effect and is useful as an active ingredient of a harmful arthropod controlling agent.

  Various substituents used in the description of the present specification will be described below with examples. In the present invention, in the description of “C2-C6 alkoxyalkyl group”, “C2-C6” means that the total number of carbon atoms forming the alkoxyalkyl group is 2-6. The same applies to the description of other substituents.

In the present specification, the following groups are defined in addition to the A group, the B group, and the C group as a group of substituents composed of specific substituents.
Group D halogen ^{atoms, -Z 2 - (T-Z} 2) r-R 10 group, ^{and, - (Z 2) p-} C (= O) - (Z 3) 1 monovalent consisting q-R ¹⁰ group A group of substituents of
Group E is a halogen atom, -R ^{12 group, -Z 2 - (T-Z} 2) r-R 10 ^{group, - (T-Z 2)} s-R 10 ^{group, - (Z 2) p-} C (= O)-(Z ³ ) q-R ¹⁰ group, -Q ³ group, -Z ² -Q ³ group, -TQ ³ group, -Z ² -TQ ³ group, and -TZ ² A group of monovalent substituents consisting of -Q ³ groups;
Group F is a group of divalent substituents consisting of an oxygen atom, a -T- group, and a -Z ⁴ -TZ ⁵ -group;

Group H is a C1-C4 alkyl group optionally substituted with a halogen atom, a C2-C4 alkenyl group optionally substituted with a halogen atom, a C2-C4 alkynyl group optionally substituted with a halogen atom, and A group of monovalent substituents consisting of halogen atoms;
Group I is a C1-C4 alkyl group optionally substituted with a halogen atom, a C1-C4 alkoxy group optionally substituted with a halogen atom, a C1-C4 alkylthio group, a halogen atom, a cyano group, a nitro group, and A group of monovalent substituents comprising a formyl group;
Group J is a group of monovalent substituents consisting of a C1-C4 alkyl group optionally substituted with a halogen atom, a C2-C4 alkynyl group, and a halogen atom;
Group K is a C1-C4 alkyl group and a group of monovalent substituents consisting of a halogen atom; and Group L is an optionally substituted C1-C4 alkyl group and a halogen atom. A good C1-C4 alkoxy group, an alkylthio group, and a group of monovalent substituents consisting of a halogen atom are each meant.
{Wherein Q ³ represents a 3- to 10-membered carbocyclic group or a 3- to 10-membered heterocyclic group, and r, p, q, s, Z ² , Z ³ , Z ⁴ , Z ⁵ , R ¹⁰ and R ¹² represents the same meaning as described above. }

Examples of “C1-C7 chain hydrocarbon group in R (wherein the chain hydrocarbon group may be substituted with one or more monovalent groups selected from group A)” include, for example, C1- C7 alkyl group, C3-C7 alkenyl group, C3-C7 alkynyl group, C1-C7 haloalkyl group, C3-C7 haloalkenyl group, C3-C7 haloalkynyl group, (C1-C7 alkoxy) C1-C7 alkyl group, {( C1-C7 alkoxy) C1-C4 alkoxy} C1-C7 alkyl group, [{(C1-C7 alkoxy) C1-C4 alkoxy} C1-C4 alkoxy] C1-C7 alkyl group, (C1-C7 haloalkoxy) C1-C7 An alkyl group, a (C3-C7 alkenyloxy) C1-C7 alkyl group, a (C3-C7 alkynyloxy) C1-C7 alkyl group, (C3-C Haloalkenyloxy) C1-C7 alkyl group, (C3-C7 haloalkynyloxy) C1-C7 alkyl group, (C1-C7 alkylthio) alkyl group, C1-C7 hydroxyiminoalkyl group, (C1-C7 alkoxyimino) C1- C7 alkyl group, (C1-C7 alkylamino) C1-C7 alkyl group, C2-C8 cyanoalkyl group, C2-C8 formylalkyl group, (C2-C8 alkanoyl) C1-C7 alkyl group, (C2-C8 alkoxycarbonyl) A C1-C7 alkyl group, a C1-C7 hydroxyalkyl group, a (C2-C8 alkylcarbonyloxy) C1-C7 alkyl group;
C1-C6 alkyl group, C3-C6 alkenyl group, C3-C6 alkynyl group, C1-C6 haloalkyl group, C3-C6 haloalkenyl group, C3-C6 haloalkynyl group, C2-C7 alkoxyalkyl group, C2-C6 alkylthioalkyl Group, C2-C6 formylalkyl group, C2-C6 cyanoalkyl group, C2-C6 hydroxyiminoalkyl group, C3-C7 alkoxyiminoalkyl group, C3-C10 alkylaminoalkyl group, C2-C6 alkoxycarbonylalkyl group, C2- A C6 hydroxyalkyl group is preferred.

  Examples of the “C3-C6 alkanoyl group” in R include a propionyl group.

  The “—Q group” in R is a 3- to 10-membered carbocyclic group (provided that the carbocyclic group is substituted with one or more substituents selected from group B, or is the same or adjacent ring member atoms. Or may be substituted with one or more substituents selected from group C above), or a 3- to 10-membered heterocyclic group (provided that the carbocyclic group is one or more substituents selected from group B) Or may be substituted with one or more substituents selected from group C on the same or adjacent ring atoms.

“3 to 10-membered carbocyclic group (provided that the carbocyclic group is substituted with one or more substituents selected from group B, or one or more selected from group C on the same or adjacent ring member atoms) As the above-mentioned ")", for example, a C3-C8 cycloalkyl group optionally substituted with one or more substituents selected from Group B and Group C, Group B and Group C A C5-C8 cycloalkenyl group which may be substituted with one or more selected substituents, and a phenyl group which may be substituted with one or more substituents selected from Group B and Group C;
C3-C8 cycloalkyl group optionally substituted with one or more substituents selected from Group H, C5-C8 cycloalkenyl group optionally substituted with one or more substituents selected from Group H, Group I Preferred is a phenyl group which may be substituted with one or more substituents selected from the above.

“3 to 10-membered heterocyclic group (provided that the carbocyclic group is substituted with one or more substituents selected from group B, or one or more selected from group C on the same or adjacent ring atoms) Is optionally substituted with one or more substituents selected from Group B and Group C, for example, a 3- to 6-membered saturated heterocyclic group (provided that The atom is only an oxygen atom or a sulfur atom.), A 3- to 6-membered saturated heterocyclic group which may be substituted with one or more substituents selected from Group B and Group C (however, the heteroatom is a nitrogen atom) 5-6 membered unsaturated heterocyclic group optionally substituted with one or more substituents selected from group B and group C (the hetero atom is only an oxygen atom or a sulfur atom) ), May be substituted with one or more substituents selected from Group B and Group C. A 6-membered unsaturated heterocyclic group (wherein the heteroatom is only a nitrogen atom), a 5- to 6-membered unsaturated group which may be substituted with one or more substituents selected from Group B and Group C A heterocyclic group (however, the hetero atom is only a sulfur atom and a nitrogen atom, or only an oxygen atom and a nitrogen atom);
5-membered heterocyclic group containing only 1 or 2 oxygen atoms as a heteroatom, 6-membered heterocyclic group containing only 1 or 2 oxygen atoms as a heteroatom, 5-membered containing only one sulfur atom as a heteroatom Heterocyclic groups, 6-membered heterocyclic groups containing only one or two sulfur atoms as heteroatoms, 5-membered heterocyclic groups containing only one or two nitrogen atoms as heteroatoms, sulfur atoms and nitrogen atoms as heteroatoms 5-membered heterocyclic group containing only oxygen, 5-membered heterocyclic group containing only oxygen and nitrogen atoms as heteroatoms, and 6-membered heterocyclic group containing only one or two nitrogen atoms as heteroatoms (provided that The ring group may be substituted with one or more substituents selected from the group B and the group C).
5-membered heterocyclic group containing only 1 or 2 oxygen atoms as a heteroatom, 6-membered heterocyclic group containing only 1 or 2 oxygen atoms as a heteroatom, 5-membered containing only one sulfur atom as a heteroatom Heterocyclic groups, 6-membered heterocyclic groups containing only one or two sulfur atoms as heteroatoms, 5-membered heterocyclic groups containing only one or two nitrogen atoms as heteroatoms, sulfur atoms and nitrogen atoms as heteroatoms 5-membered heterocyclic group containing only oxygen, 5-membered heterocyclic group containing only oxygen and nitrogen atoms as heteroatoms, and 6-membered heterocyclic group containing only one or two nitrogen atoms as heteroatoms (provided that More preferably, the ring group may be substituted with one or more substituents selected from Group I).

  The “—TQ group” in R is a 3- to 10-membered carbocyclic group (provided that the carbocyclic group is substituted with one or more substituents selected from Group B, or is the same or adjacent rings. A C1-C4 alkyl group substituted with one or more substituents selected from group C on the constituent atoms, or a 3- to 10-membered heterocyclic group (provided that the carbocyclic group) May be substituted with one or more substituents selected from Group B, or may be substituted with one or more substituents selected from Group C on the same or adjacent ring atoms. -C4 alkyl group.

“3 to 10-membered carbocyclic group (provided that the carbocyclic group is substituted with one or more substituents selected from group B, or one or more selected from group C on the same or adjacent ring member atoms) The C1-C4 alkyl group substituted by the above-mentioned substituent may be substituted with one or more monovalent substituents selected from Group B and Group C, for example. C1-C4 alkyl group substituted with a C8 cycloalkyl group, C1-C4 substituted with a C5-C8 cycloalkenyl group optionally substituted with one or more monovalent substituents selected from Group B and Group C An alkyl group, and a C1-C4 alkyl group substituted with a phenyl group which may be substituted with one or more monovalent substituents selected from Group B and Group C;
For example, a C1-C4 alkyl group substituted with a C3-C8 cycloalkyl group optionally substituted with one or more monovalent substituents selected from Group H, one or more monovalent substituents selected from Group H A C1-C4 alkyl group substituted with a C5-C8 cycloalkenyl group optionally substituted with, a C1 substituted with a phenyl group optionally substituted with one or more monovalent substituents selected from Group I Preferred is a -C4 alkyl group.

“3 to 10-membered heterocyclic group (provided that the carbocyclic group is substituted with one or more substituents selected from group B, or one or more selected from group C on the same or adjacent ring atoms) As the C1-C4 alkyl group substituted by the above-mentioned substituent (s), for example, a 3- to 6-membered group optionally substituted by one or more substituents selected from Group B and Group C A saturated heterocyclic group (however, the hetero atom is only an oxygen atom or a sulfur atom) may be substituted with a substituted C1-C4 alkyl group, one or more substituents selected from Group B and Group C 3 A 6-membered saturated heterocyclic group (however, the hetero atom is only a nitrogen atom) may be substituted with a substituted C1-C4 alkyl group, one or more substituents selected from Group B and Group C. 5- to 6-membered unsaturated heterocyclic group (provided that the heteroatom is an oxygen atom Is a sulfur atom only), a C1-C4 alkyl group substituted, and a 5- to 6-membered unsaturated heterocyclic group optionally substituted with one or more substituents selected from Group B and Group C (provided that Hetero atoms are only nitrogen atoms.) A substituted C1-C4 alkyl group, a 5- to 6-membered unsaturated heterocyclic group optionally substituted with one or more substituents selected from Group B and Group C ( Provided that the hetero atom includes only a sulfur atom and a nitrogen atom, or an oxygen atom and a nitrogen atom only), and a substituted C1-C4 alkyl group;
C1-C4 alkyl group substituted with a 5-membered heterocyclic group containing only one or two oxygen atoms as a hetero atom, C1-C4 substituted with a 6-membered heterocyclic group containing only one or two oxygen atoms as a hetero atom C1 alkyl group, C1-C4 alkyl group substituted with a 5-membered heterocyclic group containing only one sulfur atom as a hetero atom, C1 substituted with a 6-membered heterocyclic group containing only one or two sulfur atoms as a hetero atom -C4 alkyl group, C1-C4 alkyl group substituted with a 5-membered heterocyclic group containing only one or two nitrogen atoms as a hetero atom, 5-membered heterocyclic group containing only a sulfur atom and a nitrogen atom substituted as a hetero atom C1-C4 alkyl group, a C1-C4 alkyl group substituted with a 5-membered heterocyclic group containing only oxygen and nitrogen atoms as a hetero atom, or only one nitrogen atom as a hetero atom Preferred is a C1-C4 alkyl group substituted with two 6-membered heterocyclic groups (wherein the above heterocyclic group may be substituted with one or more substituents selected from Group B and Group C). Being;
C1-C4 alkyl group substituted with a 5-membered heterocyclic group containing only one or two oxygen atoms as a hetero atom, C1-C4 substituted with a 6-membered heterocyclic group containing only one or two oxygen atoms as a hetero atom C1 alkyl group, C1-C4 alkyl group substituted with a 5-membered heterocyclic group containing only one sulfur atom as a hetero atom, C1 substituted with a 6-membered heterocyclic group containing only one or two sulfur atoms as a hetero atom -C4 alkyl group, C1-C4 alkyl group substituted with a 5-membered heterocyclic group containing only one or two nitrogen atoms as a hetero atom, 5-membered heterocyclic group containing only a sulfur atom and a nitrogen atom substituted as a hetero atom C1-C4 alkyl group, a C1-C4 alkyl group substituted with a 5-membered heterocyclic group containing only oxygen and nitrogen atoms as a hetero atom, or only one nitrogen atom as a hetero atom Two containing 6-membered heterocyclic C1-C4 alkyl group which group is substituted (provided that said heterocyclic group may be substituted with one or more substituents selected from Group I.) Is exemplified more preferably.

The “—T—O—Q group” in R is a 3- to 10-membered carbocyclic group (provided that the carbocyclic group is substituted with one or more substituents selected from Group B, or is the same or adjacent) A group substituted with a C1-C4 alkyl group via an oxygen atom, or a 3- to 10-membered complex, which may be substituted with one or more substituents selected from group C A cyclic group (provided that the carbocyclic group is substituted with one or more substituents selected from group B, or is substituted with one or more substituents selected from group C on the same or adjacent ring atoms) Is a group substituted with a C1-C4 alkyl group through an oxygen atom,
For example, a phenyloxy group which may be substituted with one or more substituents selected from group B and C is substituted with a substituted C1-C4 alkyl group, one or more substituents selected from group B and C Examples thereof include a group in which a 3 to 10-membered heterocyclic group which may be substituted is substituted with a C1-C4 alkyl group via an oxygen atom.

The “—T—O—TQ group” in R is a 3- to 10-membered carbocyclic group (provided that the carbocyclic group is substituted with one or more substituents selected from Group B or the same Or a C1-C4 alkoxy group substituted with one or more substituents selected from group C on adjacent ring atoms, or a 3- to 10-membered heterocyclic group (provided that The carbocyclic group may be substituted with one or more substituents selected from Group B, or may be substituted with one or more substituents selected from Group C on the same or adjacent ring constituent atoms. Is a substituted C1-C4 alkoxy group,
Examples thereof include a C1-C4 alkyl group substituted with a benzyloxy group which may be substituted with one or more substituents selected from Group B and Group C.

Examples of the “3- to 10-membered carbocyclic group” include a C3-C8 cycloalkyl group, a C5-C8 cycloalkenyl group, a phenyl group, and a naphthyl group.
Examples of the “3- to 10-membered heterocyclic group” include a 3- to 8-membered heterocyclic group having at least one atom selected from the group consisting of an oxygen atom, a sulfur atom and a nitrogen atom as a ring constituent atom, For example, a 5-membered heterocyclic group containing only 1 or 2 oxygen atoms as a heteroatom, a 6-membered heterocyclic group containing only 1 or 2 oxygen atoms as a heteroatom, and a sulfur atom only as a heteroatom 5 5-membered heterocyclic groups, 6-membered heterocyclic groups containing only 1 or 2 sulfur atoms as heteroatoms, 5-membered heterocyclic groups containing only 1 or 2 nitrogen atoms as heteroatoms, sulfur atoms and nitrogen as heteroatoms Examples thereof include a 5-membered heterocyclic group containing only atoms, a 5-membered heterocyclic group containing only oxygen and nitrogen atoms as heteroatoms, and a 6-membered heterocyclic group containing only one or two nitrogen atoms as heteroatoms.

As the “—Z ² — (TZ ² ) r—R ¹⁰ group” in the substituents of the A group and the B group, for example, a group in which r = 0, Z ² = oxygen atom and R ¹⁰ = hydrogen atom ( Hydroxyl group); r = 0, Z ² = oxygen atom and R ¹⁰ = group which is a C1-C7 chain hydrocarbon group optionally substituted by a halogen atom (methoxy group, ethoxy group, propoxy group, isopropoxy group) , 2-propenyloxy group, 2,2,2-trifluoroethoxy group, 3,3-dichloro-2-propenyloxy group, etc.); r = 0, Z ² = sulfur atom and R ¹⁰ = substituted with halogen atom An optionally substituted C1-C7 chain hydrocarbon group (methylthio group, ethylthio group, etc.); r = 1, Z ² = oxygen atom, T = C1-C4 alkanediyl group and R ¹⁰ = substituted with a halogen atom C1-C7 chain hydrocarbons In a group (methoxymethoxy group, ethoxymethoxy group, a 2-methoxyethoxy group, 2-ethoxyethoxy group, etc.).

As the “— (Z ² ) p—C (═O) — (Z ³ ) q—R ¹⁰ group” in the substituents of the A group and the B group, for example, p = 0, q = 0 and R ¹⁰ = hydrogen A group which is an atom (formyl group); p = 0, q = 0 and R ¹⁰ = a group which is a C1-C7 chain hydrocarbon group optionally substituted by a halogen atom (acetyl group, propanoyl group, etc.); p = 1, q = 0, Z ² = oxygen atom and R ¹⁰ = hydrogen atom (formyloxy group); p = 1, q = 0, Z ² = oxygen atom and R ¹⁰ = substituted with halogen atom A group that is a C1-C7 chain hydrocarbon group (acetyloxy group, propanoyloxy group, etc.); p = 0, q = 1, Z ³ = oxygen atom and R ¹⁰ = a group that is a hydrogen atom (carboxyl Group); p = 0, q = 1, Z ³ = oxygen atom and R ¹⁰ = C1-C7 chain optionally substituted with a halogen atom Groups that are hydrocarbon groups (methoxycarbonyl group, ethoxycarbonyl group, tert-butoxycarbonyl group, etc.); p = 1, q = 1, Z ² = sulfur atom, Z ³ = —N (C1-C6 alkyl group) -Groups and R ¹⁰ = groups which are C1-C7 chain hydrocarbon groups optionally substituted with a halogen atom (such as -SC (= O) NMe ₂ group, -SC (= O) NEt ₂ group). It is done.

As the “—C (═NO—R ¹⁰ ) —R ¹¹ group” in the substituents of the A group and the B group, for example, a group in which R ¹⁰ = hydrogen atom and R ¹¹ = hydrogen atom (hydroxyiminomethyl group); R ¹⁰ = C1-C7 chain hydrocarbon group optionally substituted with a halogen atom and R ¹¹ = a group having a hydrogen atom (methoxyiminomethyl group, ethoxyiminomethyl group, etc.); R ¹⁰ = substituted with a halogen atom C1-C7 chain hydrocarbon group which may be substituted and R ¹¹ = C1-C7 chain hydrocarbon group which may be substituted with a halogen atom (2- (methoxyimino) ethyl group, 2- (ethoxy Imino) ethyl group and the like.

Examples of the “— (T—Z ² ) s—R ¹⁰ group” in the substituent of group B include, for example, s = 1, Z ² = oxygen atom, T = C 1 -C 4 alkanediyl group and R ¹⁰ = hydroxyl group ( Hydroxymethyl group, 2-hydroxyethyl group, etc.); s = 1, Z ² = oxygen atom, T = C1-C4 alkanediyl group and R ¹⁰ = C1-C7 chain hydrocarbon optionally substituted with a halogen atom Examples thereof include groups (methoxymethyl group, ethoxymethyl group, 2-methoxyethyl group, 2-ethoxyethyl group, etc.) that are groups.
As the “—Z ² -Q ¹ group” in the substituent of Group B, for example, a group in which a 3- to 10-membered carbocyclic group is bonded through an oxygen atom (phenoxy group, cyclohexyloxy group, etc.); Examples include a group in which a membered heterocyclic group is bonded via an oxygen atom (such as a 4-pyridyloxy group) and an amino group (such as a phenylamino group) substituted with a 3 to 10 membered carbocyclic group.
As the “—TQ ¹ group” in the substituent of Group B, for example, a C1-C4 alkyl group (benzyl group, cyclohexylmethyl group, etc.) substituted with a 3-10 membered carbocyclic group, 3-10 membered C1-C4 alkyl group (4-pyridylmethyl group etc.) substituted by the heterocyclic group is mentioned.
Examples of the “—Z ² -TQ ¹ group” in the substituent of Group B include a C1-C4 alkoxy group (benzyloxy group and the like) substituted with a 3 to 10-membered carbocyclic group.
Examples of the “—TZ ² -Q ¹ group” in the substituent of the group B include groups in which a 3 to 10-membered carbocyclic group is substituted with a C1-C4 alkoxy group through an oxygen atom (phenoxymethyl group, 1 -Phenoxyethyl group, etc.).

Examples of the “—Z ⁴ —TZ ⁵ — group” in the divalent substituent of the group C include, for example, a group in which Z ⁴ = oxygen atom and Z ⁵ = oxygen atom (—OCH ₂ CH ₂ O—, —OC (CH ₃ ) ₂ O— and the like.
Examples of the “—TZ ⁴ -T— group” in the divalent substituent of Group C include, for example, a group in which Z ⁴ = oxygen atom (—CH ₂ OCH ₂ —, —CH ₂ CH ₂ OCH ₂ CH ₂ — Etc.).

また、Ｃ群より選ばれる２価の置換基が、３〜１０員の炭素環基または３〜１０員の複素環基の隣接する環構成原子上にて置換された状態を、シクロヘキシル基の隣接する環構成原子上にて置換された具体例として以下に示す。

A divalent substituent selected from Group C is substituted on the same ring member atom of a 3 to 10-membered carbocyclic group or a 3 to 10-membered heterocyclic group, and the same ring of the cyclohexyl group Specific examples of substitution on the constituent atoms are shown below.

In addition, a divalent substituent selected from group C is substituted on a ring-constituting atom adjacent to a 3- to 10-membered carbocyclic group or a 3- to 10-membered heterocyclic group, adjacent to the cyclohexyl group. Specific examples of substitution on the ring-constituting atoms are shown below.

Examples of the “C1-C4 alkyl group optionally substituted with a halogen atom” in the H group substituent include a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-butyl group, a trifluoromethyl group, and a difluoro group. Examples thereof include a methyl group and a pentafluoroethyl group, and examples of the “C2-C4 alkenyl group optionally substituted with a halogen atom” include a vinyl group and an allyl group. Examples of the “optional C2-C4 alkynyl group” include an ethynyl group, and examples of the “halogen atom” include a fluorine atom and a chlorine atom.
Examples of the “C1-C4 alkyl group optionally substituted with a halogen atom” in the substituent of Group I include, for example, methyl group, ethyl group, propyl group, isopropyl group, tert-butyl group, trifluoromethyl group, difluoromethyl Group and a pentafluoroethyl group, and examples of the “C1-C4 alkoxy group optionally substituted with a halogen atom” include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a trifluoromethoxy group, Examples of the “C1-C4 alkylthio group” include a methylthio group and an ethylthio group.

  Examples of the “halogen atom” include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

  The “C1-C7 alkyl group” means a monovalent substituent of a C1-C7 linear or branched saturated hydrocarbon, for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group , Isobutyl group, sec-butyl group, tert-butyl group, pentyl group, isopentyl group, neopentyl group, sec-pentyl group, tert-pentyl group, 2-methylbutyl group, 1,2-dimethylpropyl group, 1-ethylpropyl group Group, hexyl group, 3,3-dimethylbutyl group, 1,2-dimethylbutyl group, 2-methylpentyl group, 3-methylpentyl group, 4-methylpentyl group, 2,2-dimethylbutyl group, 2,3 -Dimethylbutyl group, 2-ethylbutyl group, 1-methylpentyl group, 1,2,2-trimethylpropyl group, 1,3-dimethylbutyl group, 1-ethyl Butyl group, 1-ethyl-2-methylpropyl group, heptyl group, 1-ethyl-2,2-dimethylpropyl group, 1-methylhexyl group, 2-methylhexyl group, 3-methylhexyl group, 4-methyl Hexyl group, 5-methylhexyl group, 1,2-dimethylpentyl group, 1,3-dimethylpentyl group, 1,4-dimethylpentyl group, 2,2-dimethylpentyl group, 2,3-dimethylpentyl group, 2 , 4-dimethylpentyl group, 3,3-dimethylpentyl group, 3,4-dimethylpentyl group, 4,4-dimethylpentyl group, 1-ethylpentyl group, 2-ethylpentyl group, 3-ethylpentyl group, 1 -Propylbutyl group, 2-ethyl-1-methylbutyl group, 1-ethyl-2-methylbutyl group, 1-ethyl-3-methylbutyl group, 1-tert-butyl group Propyl group, and a 3-ethyl-4-methylbutyl group.

  The “C3-C7 alkenyl group” means a monovalent substituent of hydrocarbon having at least one double bond of C3-C6 linear or branched, for example, 2-propenyl group, 2-butenyl Group, 3-butenyl group, 1-methyl-2-butenyl group, 2-methyl-2-propenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 2-methyl-2-butenyl group, 2 -Methyl-2-butenyl group, 2-methyl-3-butenyl group, 3-methyl-2-butenyl group, 3-methyl-3-butenyl group, 1-methyl-1-butenyl group, 1-methyl-3- Butenyl group, 1,2-dimethyl-2-propenyl group, 1-ethyl-2-propenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group, 1-methyl-3-pentenyl Group, 1- Tyl-4-pentenyl group, 2-methyl-2-pentenyl group, 3-methyl-3-pentenyl group, 3-methyl-4-pentenyl group, 4-methyl-3-pentenyl group, 4-methyl-4-pentenyl group Group, 2-propyl-2-propenyl group, 1-propyl-2-propenyl group, 1,2-dimethyl-2-butenyl group, 1,2-dimethyl-3-butenyl group, 1,3-dimethyl-2- Butenyl group, 1,3-dimethyl-3-butenyl group, 1-ethyl-2-methyl-2-propenyl group, 1- (1-methylethyl) -2-propenyl group, 1-ethyl-2-butenyl group, A 1-ethyl-3-butenyl group may be mentioned.

  The “C3-C7 alkynyl group” means a monovalent substituent of hydrocarbon having at least one triple bond of C3-C6 straight chain or branched, for example, 2-propynyl group, 1-methyl- 2-propynyl group, 1,1-dimethyl-2-propynyl group, 1-ethyl-2-propynyl group, 1-propyl-2-propynyl group, 1- (1-methylethyl) -2-propynyl group, 2- Butynyl group, 1-methyl-2-butynyl group, 1-ethyl-2-butynyl group, 2-pentynyl group, 1-methyl-2-pentynyl group, 2-hexynyl group, 3-butynyl group, 1-methyl-3 Examples include -butynyl group, 1-ethyl-3-butynyl group, 3-pentynyl group, 1-methyl-3-pentynyl group, 3-hexynyl group, 4-pentynyl group, and 5-hexynyl group.

  “C1-C7 haloalkyl group” means a C1-C7 alkyl group substituted with one or more halogen atoms, for example, 2-fluoroethyl group, 2,2-difluoroethyl group, 2,2,2-trimethyl. Fluoroethyl group, 2-chloroethyl group, 2,2-dichloroethyl group, 2,2,2-trichloroethyl group, 3-chloropropyl group, 2-bromoethyl group, 2,2,2-tribromoethyl group, 3 -A bromopropyl group and 2-iodoethyl group are mentioned.

  “C3-C7 haloalkenyl group” means a C3-C7 alkenyl group substituted with one or more halogen atoms, such as 3,3-difluoro-2-propenyl group, 3,3-dichloro-2-propenyl, and the like. Group and a 3,3-dibromo-2-propenyl group.

  The “C3-C7 haloalkynyl group” means a C3-C7 alkynyl group substituted with one or more halogen atoms, and examples thereof include a 3-chloropropynyl group and a 3-bromopropynyl group.

  “(C1-C7 alkoxy) C1-C7 alkyl group” means a C1-C7 alkyl group substituted with one or more C1-C7 alkoxy groups, for example, a methoxymethyl group, 2-methoxyethyl group, 1- Methyl-2-methoxyethyl group, 2-methyl-2-methoxyethyl group, 2-ethoxyethyl group, 3-methoxypropyl group, 2,3-dimethoxypropyl group, 1-methoxymethyl-2-methoxyethyl group, 2 , 3-diethoxypropyl group, and 1-ethoxymethyl-2-ethoxyethyl group.

  Examples of the “{(C1-C7 alkoxy) C1-C4 alkoxy} C1-C7 alkyl group” include a 2- (2-methoxyethoxy) ethyl group.

  Examples of “[{(C1-C7 alkoxy) C1-C4 alkoxy} C1-C4 alkoxy] C1-C7 alkyl group” include a 2- {2- (2-methoxyethoxy) ethoxy} ethyl group.

  “(C1-C7 haloalkoxy) C1-C7 alkyl group” means a C1-C7 alkyl group substituted by one or more C1-C7 haloalkoxy groups, for example, a 2- (2-chloroethoxy) ethyl group. Is mentioned.

  The “(C3-C7 alkenyloxy) C1-C7 alkyl group” means a C1-C7 alkyl group substituted with one or more C3-C7 alkenyloxy groups, and examples thereof include a 2-allyloxyethyl group.

  “(C3-C7 alkynyloxy) C1-C7 alkyl group” means a C1-C7 alkyl group substituted with one or more C3-C7 alkynyloxy groups, for example, 2- (2-propynyloxy) ethyl group Is mentioned.

“(C3-C7 haloalkenyloxy) C1-C7 alkyl group” means a C1-C7 alkyl group substituted with one or more C1-C7 haloalkenyloxy groups, for example 2- (3-chloro-2 -Propenyloxy) ethyl group.

  The “(C1-C7 alkylthio) alkyl group” means a C1-C7 alkyl group substituted with one or more C1-C7 alkylthio groups, and examples thereof include a 2-methylthioethyl group.

  The “C1-C7 hydroxyiminoalkyl group” means a C1-C7 alkyl group substituted with one or more hydroxyimino groups, and examples thereof include a 2-hydroxyiminoethyl group.

“(C1-C7 alkoxyimino) C1-C7 alkyl group” means a C1-C7 alkyl group substituted with one or more C1-C7 alkoxyimino groups, for example, a 2- (methoxyimino) ethyl group. It is done.

  “(C1-C7 alkylamino) C1-C7 alkyl group” means a C1-C7 alkyl group substituted with one or more C1-C7 alkylamino groups, for example, a 2- (methylamino) ethyl group. It is done.

  The “C2-C8 cyanoalkyl group” means a C1-C7 alkyl group substituted with one or more cyano groups, and examples thereof include a cyanomethyl group.

  The “C2-C8 formylalkyl group” means a C1-C7 alkyl group substituted with one or more formyl groups, and examples thereof include a formylmethyl group.

  The “(C2-C8 alkanoyl) C1-C7 alkyl group” means a C1-C7 alkyl group substituted with one or more C2-C8 alkanoyl groups, and examples thereof include an acetylmethyl group.

  “(C2-C8 alkoxycarbonyl) C1-C7 alkyl group” means a C1-C7 alkyl group substituted with one or more C2-C8 alkoxycarbonyl groups, for example, a 2- (methoxycarbonyl) ethyl group. It is done.

  The “C1-C7 hydroxyalkyl group” means a C1-C7 alkyl group substituted with one or more hydroxy groups, and examples thereof include a 2-hydroxyethyl group.

  “(C2-C8 alkylcarbonyloxy) C1-C7 alkyl group” means a C1-C7 alkyl group substituted with one or more C2-C8 alkylcarbonyloxy groups, for example, a 2-acetoxyethyl group. .

Examples of the “C3-C8 cycloalkyl group optionally substituted with one or more substituents selected from Group B and Group C” include a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-butyl group, a trityl group, and the like. Substituted with one or more monovalent substituents selected from the group consisting of a fluoromethyl group, a difluoromethyl group, a pentafluoroethyl group, a vinyl group, an allyl group, an ethynyl group, a fluorine atom, a chlorine atom, and a bromine atom C3-C8 cycloalkyl group may be mentioned,
More specifically, for example, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and cyclohexyl are exemplified.

Examples of the “C5-C8 cycloalkenyl group optionally substituted with one or more substituents selected from Group B and C” include a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-butyl group, a trityl group, and the like. Substituted with one or more monovalent substituents selected from the group consisting of a fluoromethyl group, a difluoromethyl group, a pentafluoroethyl group, a vinyl group, an allyl group, an ethynyl group, a fluorine atom, a chlorine atom, and a bromine atom A C5-C8 cycloalkenyl group,
More specifically, for example, a 2-cyclohexenyl group can be mentioned.

Examples of the “phenyl group optionally substituted with one or more substituents selected from group B and group C” include, for example, methyl group, ethyl group, propyl group, isopropyl group, tert-butyl group, trifluoromethyl group, Difluoromethyl, pentafluoroethyl, methoxy, ethoxy, propoxy, isopropoxy, trifluoromethoxy, difluoromethoxy, methylthio, ethylthio, fluorine, chlorine, bromine, cyano, nitro And a phenyl group which may be substituted with one or more substituents selected from the group consisting of a group and a formyl group,
More specifically, phenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, 2-bromophenyl group, 3- Examples include a bromophenyl group and a 4-bromophenyl group.

  “3 to 10-membered heterocyclic group (provided that the carbocyclic group is substituted with one or more substituents selected from group B, or one or more selected from group C on the same or adjacent ring atoms) For example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-butyl group, a trifluoromethyl group, a difluoromethyl group, a pentafluoroethyl group, a methoxy group. , Ethoxy group, propoxy group, isopropoxy group, trifluoromethoxy group, difluoromethoxy group, methylthio group, ethylthio group, fluorine atom, chlorine atom, bromine atom, cyano group, nitro group, and formyl group A heterocyclic group which may be substituted with one or more substituents (provided that the heterocyclic group is a 5-membered heterocyclic group containing only one or two oxygen atoms as a hetero atom) Groups, 6-membered heterocyclic groups containing only one or two oxygen atoms as heteroatoms, 5-membered heterocyclic groups containing only one sulfur atom as heteroatoms, and containing one or two sulfur atoms as heteroatoms 6-membered heterocyclic group, 5-membered heterocyclic group containing only one or two nitrogen atoms as a heteroatom, 5-membered heterocyclic group containing only sulfur and nitrogen atoms as a heteroatom, oxygen atom and nitrogen atom as a heteroatom Or a 6-membered heterocyclic group containing only one or two nitrogen atoms as a hetero atom.

As the “3- to 6-membered saturated heterocyclic group optionally substituted with one or more substituents selected from Group B and Group C (wherein the heteroatom is only an oxygen atom or a sulfur atom)” For example, an oxacycloalkyl group {specifically, a tetrahydro-2-furyl group, a tetrahydro-3-furyl group, a tetrahydro-2-pyranyl group, which may be substituted with one or more substituents selected from Group B and Group C , Tetrahydro-3-pyranyl group and tetrahydro-4-pyranyl group};
Dioxolanyl group optionally substituted with one or more substituents selected from Group B and Group C (specifically, 1,3-dioxolan-4-yl group, 2-methyl-1,3-dioxolane-4- Yl group and 2,2-dimethyl-1,3-dioxolan-4-yl group};
Dioxanyl group optionally substituted with one or more substituents selected from Group B and Group C {specifically, 5-1,3-dioxanyl group, 2-methyl-5-1,3-dioxanyl group, 2 , 2-dimethyl-5-1,3-dioxanyl group};
A thiacycloalkyl group {specifically, a tetrahydro-2-thiopyranyl group, a tetrahydro-3-thiopyranyl group and a tetrahydro-4-thiopyranyl group} which may be substituted with one or more substituents selected from group B and group C}
Is mentioned.

Examples of the “3- to 6-membered saturated heterocyclic group optionally substituted with one or more substituents selected from Group B and Group C (wherein the heteroatom is only a nitrogen atom)” include, for example, Group B And a pyrrolidinyl group optionally substituted with one or more substituents selected from group C, and
Examples thereof include a piperidyl group which may be substituted with one or more substituents selected from Group B and Group C.

As the “5- to 6-membered unsaturated heterocyclic group optionally substituted with one or more substituents selected from Group B and Group C (wherein the heteroatom is only an oxygen atom or a sulfur atom)” For example,
A furyl group optionally substituted with one or more substituents selected from Group B and Group C;
A pyranyl group optionally substituted with one or more substituents selected from Group B and Group C; and
Examples include a thienyl group which may be substituted with one or more substituents selected from Group B and Group C.

Examples of the “5- to 6-membered unsaturated heterocyclic group optionally substituted with one or more substituents selected from Group B and Group C (however, the heteroatom is only a nitrogen atom)” include B A pyrrolyl group optionally substituted by one or more substituents selected from the group and group C;
A pyridyl group optionally substituted with one or more substituents selected from Group B and Group C;
A pyrimidinyl group optionally substituted with one or more substituents selected from Group B and Group C;
A pyrazinyl group optionally substituted with one or more substituents selected from Group B and Group C;
A pyridazinyl group optionally substituted with one or more substituents selected from Group B and Group C;
An imidazolyl group optionally substituted with one or more substituents selected from Group B and Group C; and
A pyrazolyl group optionally substituted by one or more substituents selected from Group B and Group C;
Is mentioned.

"5 to 6-membered unsaturated heterocyclic group optionally substituted with one or more substituents selected from Group B and Group C (provided that the heteroatom is only a sulfur atom and a nitrogen atom, or an oxygen atom and a nitrogen atom ")" Is, for example, a thiazolyl group optionally substituted by one or more substituents selected from Group B and Group C;
An isothiazolyl group optionally substituted with one or more substituents selected from Group B and Group C; and
And an isoxazolyl group optionally substituted with one or more substituents selected from Group B and Group C.

Examples of the “C1-C4 alkyl group substituted with a C3-C8 cycloalkyl group optionally substituted with one or more substituents selected from Group B and Group C” include a methyl group, an ethyl group, a propyl group, One or more 1 selected from the group consisting of isopropyl group, tert-butyl group, trifluoromethyl group, difluoromethyl group, pentafluoroethyl group, vinyl group, allyl group, ethynyl group, fluorine atom, chlorine atom, and bromine atom A C1-C4 alkyl group substituted with a C3-C8 cycloalkyl group optionally substituted with a valent substituent, and
More specifically, examples include a cyclopropylmethyl group, a cyclobutylmethyl group, a cyclopentylmethyl group, and a cyclohexylmethyl group.

Examples of the “C1-C4 alkyl group substituted with a C5-C8 cycloalkenyl group optionally substituted with one or more substituents selected from Group B and Group C” include a methyl group, an ethyl group, a propyl group, 1 or more of 1 selected from the group consisting of isopropyl group, tert-butyl group, trifluoromethyl group, difluoromethyl group, pentafluoroethyl group, vinyl group, allyl group, ethynyl group, fluorine atom, chlorine atom, and bromine atom A C1-C4 alkyl group substituted with a C5-C8 cycloalkenyl group optionally substituted with a valent substituent, and
More specifically, for example, 1-cyclohexenylmethyl group can be mentioned.

Examples of the “C1-C4 alkyl group substituted with a phenyl group optionally substituted with one or more substituents selected from Group B and C” include, for example, methyl group, ethyl group, propyl group, isopropyl group, tert group -Butyl group, trifluoromethyl group, difluoromethyl group, pentafluoroethyl group, methoxy group, ethoxy group, propoxy group, isopropoxy group, trifluoromethoxy group, difluoromethoxy group, methylthio group, ethylthio group, fluorine atom, chlorine A C1-C4 alkyl group substituted with a phenyl group which may be substituted with one or more substituents selected from the group consisting of an atom, a bromine atom, a cyano group, a nitro group, and a formyl group; Are, for example, benzyl, 2-fluorobenzyl, 3-fluorobenzyl, 4-fluorobenzyl , 2-chlorobenzyl group, 3-chlorobenzyl group, 4-chlorobenzyl group, 2-bromobenzyl group, and a 3-bromobenzyl group and a 4-bromobenzyl group.

  “3 to 10-membered heterocyclic group (provided that the carbocyclic group is substituted with one or more substituents selected from group B, or one or more selected from group C on the same or adjacent ring atoms) Examples of the C1-C4 alkyl group substituted with a substituent of (1) may include, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-butyl group, a trifluoromethyl group, and a difluoromethyl group. , Pentafluoroethyl group, methoxy group, ethoxy group, propoxy group, isopropoxy group, trifluoromethoxy group, difluoromethoxy group, methylthio group, ethylthio group, fluorine atom, chlorine atom, bromine atom, cyano group, nitro group, and A C1-C4 alkyl group substituted with a heterocyclic group which may be substituted with one or more substituents selected from the group consisting of formyl groups (provided that the heterocyclic ring Includes a 5-membered heterocyclic group containing only one or two oxygen atoms as a hetero atom, a 6-membered heterocyclic group containing only one or two oxygen atoms as a hetero atom, and only one sulfur atom as a hetero atom A 5-membered heterocyclic group, a 6-membered heterocyclic group containing only 1 or 2 sulfur atoms as a heteroatom, a 5-membered heterocyclic group containing only 1 or 2 nitrogen atoms as a heteroatom, a sulfur atom as a heteroatom, and A 5-membered heterocyclic group containing only a nitrogen atom, a 5-membered heterocyclic group containing only oxygen and nitrogen atoms as a heteroatom, or a 6-membered heterocyclic group containing only one or two nitrogen atoms as a heteroatom .).

"C1 substituted by a 3-6 membered saturated heterocyclic group optionally substituted with one or more substituents selected from Group B and Group C (wherein the heteroatom is only an oxygen atom or a sulfur atom). As the “—C4 alkyl group”, for example, a C1-C4 alkyl group substituted with an oxacycloalkyl group optionally substituted with one or more substituents selected from Group B and Group C {specifically, for example, tetrahydro 2-furylmethyl group, tetrahydro-3-furylmethyl group, tetrahydro-2-pyranylmethyl group, tetrahydro-3-pyranylmethyl group and tetrahydro-4-pyranylmethyl group};
A C1-C4 alkyl group substituted with a dioxolanyl group optionally substituted with one or more substituents selected from Group B and Group C; specifically, for example, (1,3-dioxolan-4-yl) methyl Group, (2-methyl-1,3-dioxolan-4-yl) methyl group, (2,2-dimethyl-1,3-dioxolan-4-yl) methyl group, 1- (2,2-dimethyl-1) , 3-dioxolan-4-yl) ethyl group and 2- (2,2-dimethyl-1,3-dioxolan-4-yl) ethyl group};
A C1-C5 alkyl group substituted with a dioxanyl group optionally substituted with one or more substituents selected from Group B and Group C (specifically, (5-1,3-dioxanyl) methyl group, (2 -Methyl-5-1,3-dioxanyl) methyl group, (2,2-dimethyl-5-1,3-dioxanyl) methyl group, 1- (2,2-dimethyl-5-1,3-dioxanyl) ethyl Group and 2- (2,2-dimethyl-5-1,3-dioxanyl) ethyl group}; and
C1-C4 alkyl group substituted by the thiacycloalkyl group which may be substituted by one or more substituents chosen from B group and C group is mentioned.

"C1-C4 alkyl substituted with a 3-6 membered saturated heterocyclic group (however, the heteroatom is only a nitrogen atom) optionally substituted with one or more substituents selected from Group B and Group C As the “group”, for example, a C1-C4 alkyl group substituted with a pyrrolidinyl group optionally substituted with one or more substituents selected from Group B and Group C, and
C1-C4 alkyl group substituted by the piperidyl group which may be substituted by 1 or more substituents chosen from B group and C group is mentioned.

“A 5- to 6-membered unsaturated heterocyclic group which is optionally substituted with one or more substituents selected from Group B and Group C (wherein the heteroatom is only an oxygen atom or a sulfur atom) is substituted. As the “C1-C4 alkyl group”, for example, a C1-C4 alkyl group substituted with a furyl group optionally substituted with one or more substituents selected from Group B and Group C, and
C1-C4 alkyl group substituted by the thienyl group which may be substituted by the 1 or more substituent chosen from B group and C group is mentioned.

“C1-C4 substituted with a 5- to 6-membered unsaturated heterocyclic group (however, the heteroatom is only a nitrogen atom) optionally substituted with one or more substituents selected from Group B and Group C As the “alkyl group”, for example, a C1-C4 alkyl group substituted with a pyrrolyl group optionally substituted with one or more substituents selected from Group B and Group C,
A C1-C4 alkyl group substituted with a pyridyl group optionally substituted with one or more substituents selected from Group B and Group C;
A C1-C4 alkyl group substituted with a pyrimidinyl group optionally substituted with one or more substituents selected from Group B and Group C;
A C1-C4 alkyl group substituted with a pyrazinyl group optionally substituted with one or more substituents selected from Group B and Group C;
A C1-C4 alkyl group substituted with a pyridazinyl group optionally substituted with one or more substituents selected from Group B and Group C;
A C1-C4 alkyl group substituted with an imidazolyl group optionally substituted with one or more substituents selected from Group B and Group C; and
C1-C4 alkyl group substituted by the pyrazolyl group which may be substituted by 1 or more substituents chosen from B group and C group is mentioned.

"5 to 6-membered unsaturated heterocyclic group optionally substituted with one or more substituents selected from Group B and Group C (provided that the heteroatom is only a sulfur atom and a nitrogen atom, or an oxygen atom and a nitrogen atom As the C1-C4 alkyl group substituted by, for example, a C1-C4 alkyl group substituted with a thiazolyl group optionally substituted with one or more substituents selected from Group B and Group C,
A C1-C4 alkyl group substituted with an isothiazolyl group optionally substituted with one or more substituents selected from Group B and Group C;
A C1-C4 alkyl group substituted with an izoxazolyl group optionally substituted with one or more substituents selected from Group B and Group C; and
C1-C4 alkyl group substituted by the oxazolyl group which may be substituted by 1 or more substituents chosen from B group and C group is mentioned.

  Examples of the “C1-C4 alkyl group substituted with one or more substituents selected from group B and group C which may be substituted” include a 2-phenyloxyethyl group.

  Examples of the “group in which a 3- to 10-membered heterocyclic group optionally substituted with one or more substituents selected from Group B and Group C is substituted with a C1-C4 alkyl group via an oxygen atom” include B And a C1-C4 alkyl group substituted with a thiadiazolyloxy group which may be substituted with one or more substituents selected from the group and group C.

  Examples of the “C1-C4 alkyl group substituted with one or more substituents selected from group B and group C which are optionally substituted by a benzyloxy group” include a 2-benzyloxyethyl group.

As an aspect of this invention compound, the following aspects are mentioned, for example.
"Aspect 1"
In formula (I):
R is a C1-C7 chain hydrocarbon group (provided that the chain hydrocarbon group may be substituted with one or more substituents selected from group A), -Q group, -TQ group, -T-O-Q group or -T-O-TQ group,
Q is a 3- to 10-membered carbocyclic group (provided that the carbocyclic group may be substituted with one or more substituents selected from Group B, and selected from Group C on the same or adjacent ring member atoms) Or a 3- to 10-membered heterocyclic group (provided that the heterocyclic group may be substituted with one or more substituents selected from Group B). And may be substituted with one or more substituents selected from group C on the same or adjacent ring-constituting atoms).
A thiadiazole compound in which T is a C1-C4 alkanediyl group.

“Aspect 2”
In formula (I):
R is a C1-C7 chain hydrocarbon group (provided that the chain hydrocarbon group may be substituted with one or more substituents selected from group D), -Q ² group, -TQ ² A group, -T-O-Q ² group, or -T-O-TQ ² group,
Q ² is a 3- to 10-membered carbocyclic group (provided that the carbocyclic group may be substituted with one or more substituents selected from the E group, and from the F group on the same or adjacent ring-constituting atoms) Optionally substituted with one or more selected substituents), or a 3- to 10-membered heterocyclic group (provided that the heterocyclic group is substituted with one or more substituents selected from Group E) And may be substituted with one or more substituents selected from group F on the same or adjacent ring-constituting atoms).
A thiadiazole compound in which T is a C1-C4 alkanediyl group.

“Aspect 3”
In formula (I):
R is a C1-C7 chain hydrocarbon group (provided that the chain hydrocarbon group may be substituted with one or more substituents selected from group D), -Q ⁴ group, -TQ ⁴ A group, -T-O-Q ⁴ group, or -T-O-TQ ⁴ group,
Q ⁴ is a 3- to 6-membered carbocyclic group (provided that the carbocyclic group may be substituted with one or more substituents selected from group B, and from the C group on the same or adjacent ring member atoms) Or a 3 to 6-membered saturated heterocyclic group (provided that the heterocyclic group is substituted with one or more substituents selected from group B). And may be substituted with one or more substituents selected from group C on the same or adjacent ring atoms.
A thiadiazole compound in which T is a C1-C4 alkanediyl group.

で示される基であり、
ｔは０または１であり、
Ｒ¹³およびＲ¹⁴は各々独立して、水素原子、Ｃ１−Ｃ４アルキル基、Ｃ２−Ｃ７アルケニル基、Ｃ２−Ｃ４アルキニル基、Ｃ１−Ｃ４アルコキシアルキル基、Ｃ２−Ｃ４ハロアルキル基、または、-Ｑ⁸基であるか、もしくは、Ｒ¹³およびＲ¹⁴が末端で結合してＣ２−Ｃ７アルカンジイル基、または、-Ｚ⁴-Ｔ-Ｚ⁵-基であり、
Ｑ⁸が３〜１０員の炭素環基（但し、該炭素環基は上記Ｄ群より選ばれる１以上の置換基で置換されていてもよく、同一または隣接する環構成原子上にて上記Ｆ群より選ばれる１以上の置換基で置換されていてもよい。）、または、３〜１０員の複素環基（但し、該複素環基は上記Ｄ群より選ばれる１以上の置換基で置換されていてもよく、同一または隣接する環構成原子上にて上記Ｆ群より選ばれる１以上の２価の置換基で置換されていてもよい。）を表す。｝であり、
Ｚ⁴およびＺ⁵は各々独立して、酸素原子または硫黄原子であり、
ＴがＣ１−Ｃ４アルカンジイル基であるチアジアゾール化合物。 “Aspect 4”
In formula (I):
R is a C1-C7 chain hydrocarbon group (provided that the chain hydrocarbon group may be substituted with one or more substituents selected from group D), -Q ⁶ group, -TQ ⁶ A group, —T—O—Q ⁶ group, or —T—O—TQ ⁶ group,
Q ⁶ is a 3- to 6-membered carbocyclic group (provided that the carbocyclic group may be substituted with one or more substituents selected from the E group, and from the F group on the same or adjacent ring-constituting atoms) Or a 3 to 6-membered saturated heterocyclic group (provided that the heterocyclic group is substituted with one or more substituents selected from Group E). And may be substituted with one or more substituents selected from group F on the same or adjacent ring-constituting atoms).
A thiadiazole compound in which T is a C1-C4 alkanediyl group.
“Aspect 5”
In formula (I):
R is a C1-C7 chain hydrocarbon group (provided that the chain hydrocarbon group may be substituted with one or more substituents selected from group D), -Q ⁷ group or -TQ ⁷ Group,
Q ⁷ is a C3-C8 cycloalkyl group (provided that the cycloalkyl group may be substituted with one or more substituents selected from Group E, and is selected from Group F on the same or adjacent ring member atoms) Optionally substituted with one or more substituents), or

A group represented by
t is 0 or 1;
R ¹³ and R ¹⁴ are each independently a hydrogen atom, a C1-C4 alkyl group, a C2-C7 alkenyl group, a C2-C4 alkynyl group, a C1-C4 alkoxyalkyl group, a C2-C4 haloalkyl group, or -Q ⁸ A group, or R ¹³ and R ¹⁴ are bonded at the end to form a C2-C7 alkanediyl group, or a -Z ⁴ -TZ ⁵ -group,
Q ⁸ is a 3- to 10-membered carbocyclic group (provided that the carbocyclic group may be substituted with one or more substituents selected from the above-mentioned group D, and the above F on the same or adjacent ring-constituting atoms. Substituted with one or more substituents selected from the group), or a 3- to 10-membered heterocyclic group (provided that the heterocyclic group is substituted with one or more substituents selected from Group D above) And may be substituted with one or more divalent substituents selected from the above-mentioned group F on the same or adjacent ring-constituting atoms. },
Z ⁴ and Z ⁵ are each independently an oxygen atom or a sulfur atom,
A thiadiazole compound in which T is a C1-C4 alkanediyl group.

で示される基であり、
ｔは０または１であり、
Ｒ¹³およびＲ¹⁴は各々独立して、水素原子、Ｃ１−Ｃ４アルキル基、Ｃ２−Ｃ７アルケニル基、Ｃ２−Ｃ４アルキニル基、Ｃ１−Ｃ４アルコキシアルキル基、または、-Ｑ⁸基であるか、もしくは、Ｒ¹³およびＲ¹⁴が末端で結合してＣ２−Ｃ７アルカンジイル基、または、-Ｚ⁴-Ｔ-Ｚ⁵-基であり、
Ｑ⁸が３〜１０員の炭素環基（但し、該炭素環基は上記Ｄ群より選ばれる１以上の置換基で置換されていてもよく、同一または隣接する環構成原子上にて上記Ｆ群より選ばれる１以上の置換基で置換されていてもよい。）、または、３〜１０員の複素環基（但し、該複素環基は上記Ｄ群より選ばれる１以上の置換基で置換されていてもよく、同一または隣接する環構成原子上にて上記Ｆ群より選ばれる１以上の２価の置換基で置換されていてもよい。）を表す。｝であり、
Ｚ⁴およびＺ⁵は各々独立して、酸素原子または硫黄原子であり、
ＴがＣ１−Ｃ４アルカンジイル基であるチアジアゾール化合物。 “Aspect 6”
In formula (I):
R is a C1-C7 chain hydrocarbon group (provided that the chain hydrocarbon group may be substituted with one or more substituents selected from group D), -Q ⁷ group or -TQ ⁷ Group,
Q ⁷ is a C3-C8 cycloalkyl group (provided that the cycloalkyl group may be substituted with one or more substituents selected from Group E, and is selected from Group F on the same or adjacent ring member atoms) Optionally substituted with one or more substituents), or

A group represented by
t is 0 or 1;
R ¹³ and R ¹⁴ are each independently a hydrogen atom, C1-C4 alkyl group, C2-C7 alkenyl, C2-C4 alkynyl group, C1-C4 alkoxyalkyl group, or whether it is -Q ⁸ group, or , R ¹³ and R ¹⁴ are bonded at the end to form a C2-C7 alkanediyl group, or a —Z ⁴ -TZ ⁵ — group,
Q ⁸ is a 3- to 10-membered carbocyclic group (provided that the carbocyclic group may be substituted with one or more substituents selected from the above-mentioned group D, and the above F on the same or adjacent ring-constituting atoms. Substituted with one or more substituents selected from the group), or a 3- to 10-membered heterocyclic group (provided that the heterocyclic group is substituted with one or more substituents selected from Group D above) And may be substituted with one or more divalent substituents selected from the above-mentioned group F on the same or adjacent ring-constituting atoms. },
Z ⁴ and Z ⁵ are each independently an oxygen atom or a sulfur atom,
A thiadiazole compound in which T is a C1-C4 alkanediyl group.

“Aspect 7”
In formula (I):
R is a C1-C7 chain hydrocarbon group (provided that the chain hydrocarbon group may be substituted with one or more substituents selected from group D), -Q ⁹ group or -TQ ⁹ Group,
Q ⁹ is a phenyl group (provided that the phenyl group may be substituted with one or more substituents selected from group E), or a 5- to 6-membered unsaturated heterocyclic group (provided that the unsaturated group) And the heterocyclic group may be substituted with one or more substituents selected from the group E).
A thiadiazole compound in which T is a C1-C4 alkanediyl group.

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

  The compound of the present invention can be produced, for example, by the following production method.

で示される化合物１モルに対して、式（ｂ）
Ｒ−ＯＨ （ｂ）
〔式中、Ｒは上記と同じ意味を表す〕
で示されるアルコール化合物２モル以上を、通常塩基の存在下に反応させることにより製造することができる。
該反応は、通常、溶媒中で行なわれる。
反応に用いられる溶媒としては、例えば、ヘキサン、ヘプタン等の脂肪族炭化水素、トルエン、キシレン等の芳香族炭化水素、ジエチルエーテル、メチル−ｔｅｒｔ−ブチルエーテル、テトラヒドロフラン、１，４−ジオキサン、１，２−ジメトキシエタン等のエーテル、Ｎ，Ｎ−ジメチルホルムアミド、Ｎ−メチルピロリドン等の非プロトン性極性溶媒、および、これらの混合物等が挙げられる。
該反応に用いられる塩基としては、例えば、水酸化ナトリウム、水酸化カリウム、水酸化カルシウム等のアルカリ金属もしくはアルカリ土類金属の水酸化物、または水素化ナトリウム、水素化カリウム、水素化カルシウム等のアルカリ金属もしくはアルカリ土類金属の水素化物が挙げられる。
式（ａ）で示される化合物１モルに対して、式（ｂ）で示されるアルコール化合物は２モル以上であるが、通常２モル〜４モルの割合である。式（ｂ）で示されるアルコール化合物を過剰に用いる場合は、上記の溶媒を使用しないで反応を行うこともできる。
該反応の反応温度は、通常−７８℃〜１００℃の範囲であり、反応時間は、通常０．１〜４８時間の範囲である。
反応終了後は、例えば、反応混合物を水に注加し、有機溶媒抽出してから、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、本発明化合物を単離することができる。単離された本発明化合物は、再結晶、カラムクロマトグラフィー等により、さらに精製することができる。 (Production method 1-1)
Formula (a)

With respect to 1 mole of the compound represented by formula (b)
R-OH (b)
[Wherein R represents the same meaning as described above]
It can manufacture by making 2 mol or more of alcohol compounds shown by reacting in presence of a base normally.
The reaction is usually performed in a solvent.
Examples of the solvent used in the reaction include aliphatic hydrocarbons such as hexane and heptane, aromatic hydrocarbons such as toluene and xylene, diethyl ether, methyl-tert-butyl ether, tetrahydrofuran, 1,4-dioxane, 1,2 -Ethers such as dimethoxyethane, aprotic polar solvents such as N, N-dimethylformamide and N-methylpyrrolidone, and mixtures thereof.
Examples of the base used in the reaction include alkali metal or alkaline earth metal hydroxides such as sodium hydroxide, potassium hydroxide and calcium hydroxide, or sodium hydride, potassium hydride and calcium hydride. Alkali metal or alkaline earth metal hydrides may be mentioned.
The amount of the alcohol compound represented by the formula (b) is 2 moles or more with respect to 1 mole of the compound represented by the formula (a), but the ratio is usually 2 moles to 4 moles. When the alcohol compound represented by the formula (b) is used in excess, the reaction can be carried out without using the above solvent.
The reaction temperature of the reaction is usually in the range of −78 ° C. to 100 ° C., and the reaction time is usually in the range of 0.1 to 48 hours.
After completion of the reaction, for example, the compound of the present invention can be isolated by performing post-treatment operations such as pouring the reaction mixture into water and extracting the mixture with an organic solvent, and then drying and concentrating the organic layer. . The isolated compound of the present invention can be further purified by recrystallization, column chromatography or the like.

(Production method 1-2)
Formula (a)
With respect to 1 mol of the compound represented by formula (b ′)
R-OM (b ′)
[Wherein, M represents an alkali metal such as sodium or potassium, and R represents the same meaning as described above.]
It can manufacture by making 2 mol or more of organometallic compounds shown by react.
The reaction is usually performed in a solvent.
Examples of the solvent used in the reaction include aliphatic hydrocarbons such as hexane and heptane, aromatic hydrocarbons such as toluene and xylene, diethyl ether, methyl-tert-butyl ether, tetrahydrofuran, 1,4-dioxane, 1,2 Examples include ethers such as -dimethoxyethane, aprotic polar solvents such as N, N-dimethylformamide and N-methylpyrrolidone, alcohol compounds represented by the formula (b), and mixtures thereof.
The amount of the organometallic compound represented by the formula (b ′) is 2 mol or more with respect to 1 mol of the compound represented by the formula (a), but it is usually in a ratio of 2 mol to 4 mol.
The reaction temperature of the reaction is usually in the range of −78 ° C. to 100 ° C., and the reaction time is usually in the range of 0.1 to 48 hours.
After completion of the reaction, for example, the compound of the present invention can be isolated by performing post-treatment operations such as pouring the reaction mixture into water and extracting the mixture with an organic solvent, and then drying and concentrating the organic layer. . The isolated compound of the present invention can be further purified by recrystallization, column chromatography or the like.

〔式中、Ｒは上記と同じ意味を表す。〕
で示される化合物を、酸化剤の存在下に反応させることにより製造することができる。
該反応は、通常、溶媒中で行なわれる。
反応に用いられる溶媒としては、例えば、アセトン、メチルエチルケトン等のケトン、トルエン、キシレン等の芳香族炭化水素、ジエチルエーテル、メチル−ｔｅｒｔ−ブチルエーテル、テトラヒドロフラン、１，４−ジオキサン、１，２−ジメトキシエタン等のエーテル、Ｎ，Ｎ−ジメチルホルムアミド、Ｎ−メチルピロリドン等の非プロトン性極性溶媒、酢酸、水、およびこれらの溶媒の混合物等が挙げられる。
該反応に用いられる酸化剤としてはヨウ素等のハロゲン、過酸化水素および酸素等が挙げられる。
式（ｃ）で示される化合物１モルに対して、酸化剤が通常１〜１．５当量の割合である。
該反応の反応温度は、通常０℃〜１００℃の範囲であり、反応時間は、通常０．１〜２４時間の範囲である。
反応終了後は、例えば、反応混合物を水に注加し、有機溶媒抽出してから、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、本発明化合物を単離することができる。単離された本発明化合物は、再結晶、カラムクロマトグラフィー等により、さらに精製することができる (Production method 2)
Formula (c)

[Wherein R represents the same meaning as described above. ]
Can be produced by reacting in the presence of an oxidizing agent.
The reaction is usually performed in a solvent.
Examples of the solvent used in the reaction include ketones such as acetone and methyl ethyl ketone, aromatic hydrocarbons such as toluene and xylene, diethyl ether, methyl tert-butyl ether, tetrahydrofuran, 1,4-dioxane, and 1,2-dimethoxyethane. And aprotic polar solvents such as N, N-dimethylformamide and N-methylpyrrolidone, acetic acid, water, and mixtures of these solvents.
Examples of the oxidizing agent used in the reaction include halogen such as iodine, hydrogen peroxide and oxygen.
An oxidizing agent is a ratio of 1-1.5 equivalent normally with respect to 1 mol of compounds shown by Formula (c).
The reaction temperature of the reaction is usually in the range of 0 ° C to 100 ° C, and the reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, for example, the compound of the present invention can be isolated by performing post-treatment operations such as pouring the reaction mixture into water and extracting the mixture with an organic solvent, and then drying and concentrating the organic layer. . The isolated compound of the present invention can be further purified by recrystallization, column chromatography, etc.

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

で示される化合物またはその塩（塩酸塩、酢酸塩、硫酸塩等）と、パークロロメチルメルカプタン（トリクロロメチルスルフェニル=クロリド；Trichloromethylsulphenyl chloride）とを反応させることにより製造することができる。
該反応は、通常、塩基の存在下で行われ、通常、溶媒中で行なわれる。
反応に用いられる溶媒としては、例えば、酢酸エチル等のエステル、塩化メチレン、クロロホルム等のハロゲン化炭化水素、トルエン、キシレン等の芳香族炭化水素、およびジエチルエーテル、メチル−ｔｅｒｔ−ブチルエーテル、テトラヒドロフラン、１，４−ジオキサン、１，２−ジメトキシエタン等のエーテル等の有機溶媒、これら有機溶媒の混合物、並びに、これら有機溶媒と水との混合物が挙げられる
該反応に用いられる塩基としては、例えば、水酸化ナトリウム等のアルカリ金属もしくはアルカリ土類金属の水酸化物、炭酸水素ナトリウム、炭酸ナトリウム、炭酸カリウム等の無機塩基が挙げられる。
式（ｄ）で示される化合物１モルに対して、パークロロメチルメルカプタンが通常１〜１．５モルの割合、塩基が通常４〜６モルの割合である。
該反応の反応温度は、通常０℃〜１００℃の範囲であり、反応時間は、通常０．１〜４８時間の範囲である。
反応終了後は、例えば、反応混合物を水に注加し、有機溶媒抽出してから、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、式（ａ）で示される化合物を単離することができる。単離された式（ａ）で示される化合物は、再結晶、カラムクロマトグラフィー等により、さらに精製することができる (Reference production method 1)
The production intermediate of the compound of the present invention represented by the formula (a) has the formula (d)

Or a salt thereof (hydrochloride, acetate, sulfate, etc.) and perchloromethyl mercaptan (trichloromethylsulfenyl chloride).
The reaction is usually performed in the presence of a base, and is usually performed in a solvent.
Examples of the solvent used in the reaction include esters such as ethyl acetate, halogenated hydrocarbons such as methylene chloride and chloroform, aromatic hydrocarbons such as toluene and xylene, and diethyl ether, methyl-tert-butyl ether, tetrahydrofuran, 1 An organic solvent such as ether such as 1,4-dioxane, 1,2-dimethoxyethane, a mixture of these organic solvents, and a mixture of these organic solvents and water. Examples of the base used in the reaction include water. Inorganic bases such as alkali metal or alkaline earth metal hydroxides such as sodium oxide, sodium hydrogen carbonate, sodium carbonate, potassium carbonate and the like can be mentioned.
Perchloromethyl mercaptan is usually in the proportion of 1 to 1.5 mol and the base is usually in the proportion of 4 to 6 mol with respect to 1 mol of the compound represented by the formula (d).
The reaction temperature of the reaction is usually in the range of 0 ° C to 100 ° C, and the reaction time is usually in the range of 0.1 to 48 hours.
After completion of the reaction, for example, the compound represented by the formula (a) is simply obtained by performing post-treatment operations such as pouring the reaction mixture into water, extracting with an organic solvent, and drying and concentrating the organic layer. Can be separated. The isolated compound represented by the formula (a) can be further purified by recrystallization, column chromatography or the like.

(Reference production method 2)
The compound represented by the formula (d) or a hydrochloride thereof can be produced by reacting dimethylcarbamoyl chloride with thiourea.
The reaction is usually performed in a solvent.
Examples of the solvent used in the reaction include alcohols such as methanol and ethanol, ethers such as diethyl ether, methyl-tert-butyl ether, tetrahydrofuran, 1,4-dioxane and 1,2-dimethoxyethane, toluene, xylene and the like. Aromatic hydrocarbons or halogenated hydrocarbons such as methylene chloride and chloroform can be mentioned.
The carbamoyl chloride compound represented by the formula (d) is usually in a ratio of 1 to 1.5 mol with respect to 1 mol of thiourea.
The reaction temperature of the reaction is usually in the range of 0 ° C to 100 ° C, and the reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, for example, the compound represented by the formula (d) is simply obtained by performing post-treatment operations such as pouring the reaction mixture into water and extracting the organic solvent, and then drying and concentrating the organic layer. Can be separated. The isolated compound represented by the formula (d) can be further purified by recrystallization or the like. In addition, for example, the hydrochloride of the compound represented by the formula (d) can be isolated by filtering out crystals generated by an operation such as concentration of the reaction mixture under reduced pressure. The isolated hydrochloride of the compound represented by the formula (d) can be further purified by recrystallization or the like.

(Reference production method 3)
The organometallic compound represented by the formula (b ′) is a commercially available product, or an alcohol compound represented by the formula (b), an alkali metal such as sodium, a metal hydride compound such as sodium hydride or lithium borohydride. What was adjusted by making it react can be used.

  The alcohol compound represented by the formula (b) is a known compound, or can be produced from a known compound according to a known method.

  In the compound of the present invention, isomers such as geometrical isomers and stereoisomers can exist, but in the present invention, each of these isomers alone and mixtures thereof are included in the compound of the present invention.

  Examples of harmful arthropods for which the compounds of the present invention are effective include harmful insects and harmful mites, and specific examples thereof include the following.

  Hemiptera: Pepper (Laodelphax striatellus), brown planthopper (Nilaparvata lugens), leafhopper (Sogatella furcifera) and other species, Nephotettix cincticeps, Nephotettip Leafhoppers, cotton aphids (Aphis gossypii), peach aphids (Myzus persicae), radish aphids (Brevicoryne brassicae), snowy aphids (Aphis spiraecola), tulip mustard aphids (Macrosiphum euphorbiae), potato aphids Aphids such as aphids (Rhopalosiphum padi), citrus black aphids (Toxoptera citricidus), peach beetles (Hyalopterus pruni), Nezara antennata, hosohelika Riptortus clavetus, Leptocorisa chinensis, Eysarcoris parvus, Halyomorpha mista, etc., Trialeurodes vaporariorum, Tribaleuros vaporariorum, Tobacco emisia Whitefly, such as Bemisia argentifolii, citrus whitefly (Dialeurodes citri), whitefly (Aleurocanthus spiniferus), red beetle (Aonidiella aurantii), safflower scale (Comstockaspis perniciosa), citrus snow scale (Unaspis tris) ), Icerya purchasi, Planococcus kraunhiae, Pseudococcus longispinis, Pseudaulacaspis pentagona, etc. Ramushi such, tingidae acids, psyllid, and the like.

  Lepidopterous insects: Chilo suppressalis, Tryporyza incertulas, Cnaphalocrocis medinalis, Notarcha derogata, Plodia interpunctella, Odaltrihis, Ostrinia furnacalis, Ostrinia furnacalis Common moths such as Pediasia teterrellus, Spodoptera litura, Spodoptera exigua, Pseudaletia separata, Mamestra brassicae, Agrotis ipsilon, Agrotis ipsilon, Heliotis genus, Helicobelpa genus moths, white butterflies (Pieris rapae), etc. Mushiga (Matsumuraeses azukivora), Apple cockroach (Adoxophyes orana fasciata), Chanokokumonmonaki (Adoxophyes sp.), Chamonaki (Homona magnanima), Midarekamonmonki (Archips fuscocupreanus) Chanohosoga (Caloptilia theivora), Golden moth Hosoga (Phyllonorycter ringoneella) Hosogaga, Carposina niponensis, etc. Sugas, cotton moths (Pectinophora gossypiella) potato moths (Phthorimaea operculella), etc., tigers such as Hyphantria cunea, tigers (Tinea translucens), Hirosukoga such as Tineola bisselliella, etc.

  Thrips pests: Citrus thrips (Frankliniella occidentalis), Thrips parmi, Scirtothrips dorsalis, Thrips tabaci, ella thrips

  Diptera: Musca domestica, Culex popiens pallens, Cattle fly (Tabanus trigonus), Onion fly (Hylemya antiqua), Flyfly (Hylemya platura), Sycaenidae (Anopheles sinensis), Aye grouse flies Hydrellia griseola, Chlorops oryzae, Dacus cucurbitae, Ceratitis capitata, Bean-spotted fly (Liriomyza trifolii), Tomato-spotted leaf (Liriomyza trifolii)

  Coleopterous pests: Epilachna vigintioctopunctata, Aulacophora femoralis, Phyllotreta striolata, Oulema oryzth, Lyz (Echinocnemus squameus), Echinocnemus squameus, Echinocnemus squameus, Echinocnemus squameus Azuki beetle (Callosobruchus chinensis), Sphenophorus venatus, beetle (Popillia japonica), Anomala cuprea, corn rootworm mate (Diabrotica spp.), Colorado potato beetle (Leptinotarsa decemline squirrel) spp.), tobacco beetle (Lasioderma serricorne), Anthrenus verbasci, Tribolium castaneum, Lyctus brunneus, Anoplophora malasiaca), Toxus piniperda, etc.

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

  Hymenoptera: Athalia rosae, Achillyrmex spp., Fire ant (Solenopsis spp.), Etc.

  Cockroach eye pest: German cockroach (Blattella germanica), Black cockroach (Periplaneta fuliginosa), American cockroach (Periplaneta americana), Great cockroach (Periplaneta brunnea), Great cockroach (Blatta orientalis), etc.

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

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

  Termite pests: Yamato termites (Reticulitermes speratus), termites (Coptotermes formosanus), etc.

  Acarid pests: Nite spider mite (Tetranychus urticae), Kanzawa spider mite (Tetranychus kanzawai), Scarlet spider mite (Panonychus citri) Apple spider mite (Panonychus ulmi), Oligonicus spp. Tomato rustic mites (Aculops lycopersici), Chinese radish mites (Calacarus carinatus), Chinese radish mites (Acaphylla theavagrans), red ticks (Eriophyes chibaensis) and other ticks (Polyphagotarsonemus latus) Scarlet mites, mosquito spider mites, Haemaphysalis longicornis, Yamato tick (Haemaphysalis flava), Dermacentor taiwanicus, Yamato tick (Ixodes ovatus), Shulz tick (Ixodes p ersulcatus, tick such as Boophilus microplus, Rhipicephalus sanguineus, tick such as Tyrophagus putrescentiae, tyrophagogo mite, ides D Leopard mites, such as horned ticks (Cheyletus eruditus), tsume mites (Cheyletus malaccensis), tsume mites (Cheyletus moorei), etc.

  The harmful arthropod control agent of the present invention may be the compound of the present invention itself, but usually the compound of the present invention and an inert carrier such as a solid carrier, a liquid carrier, a gaseous carrier, etc. are mixed, if necessary, Add surfactants and other formulation adjuvants to prepare emulsions, oils, powders, granules, wettable powders, flowables, microcapsules, aerosols, smokers, poison baits, resin formulations, etc. It may be made. These preparations usually contain 0.01 to 95% by weight of the compound of the present invention relative to the whole preparation.

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

  Examples of the liquid carrier include water, alcohol (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, isobutyronitrile, etc.) , Ether (diisopropyl ether, 1,4-dioxane, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether, 3-methoxy-3-methyl-1-butanol, etc.), acid amide (N, N-dimethylformamide, N, N-dimethylacetamide, etc.), halogenated hydrocarbons (dichloromethane, trichloroethane, carbon tetrachloride, etc.), sulfoxide (dimethylsulfoxide, etc.), propylene carbonate, or vegetable oils (soybean oil, cottonseed oil, etc.) ) And the like.

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

  Examples of the surfactant include nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, and polyethylene glycol fatty acid ester, or alkyl sulfonate, alkyl benzene sulfonate, alkyl sulfate, and the like. Anionic surfactants may be mentioned.

  Other formulation adjuvants include sticking agents, dispersants, colorants, or stabilizers, such as casein, gelatin, saccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives. , Bentonite, synthetic water-soluble polymers (polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylic acids, etc.), PAP (isopropyl acid phosphate), BHT (2,6-di-tert-butyl-4-methylphenol), BHA (2 -Tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol).

  The method for controlling harmful arthropods according to the present invention usually uses the harmful arthropod control agent of the present invention as harmful arthropods or habitats of harmful arthropods (plants, soil, indoors, animals, etc.). ) Can be applied.

When the harmful arthropod control agent of the present invention is used for controlling harmful arthropods in the agricultural field, the application amount is usually 1 to 10,000 g in terms of the amount of the compound of the present invention per 10,000 m ² . When the harmful arthropod control agent of the present invention is formulated into an emulsion, a wettable powder, a flowable agent, etc., it is usually diluted with water so that the active ingredient concentration becomes 0.01 to 10,000 ppm. The applied granules, powders, etc. may be applied as they are.
These preparations and water dilutions of these preparations may be applied directly to harmful arthropods or plants such as crops to be protected from harmful arthropods, and harmful nodules that inhabit cultivated soil The soil may be treated to control paw animals.
Moreover, you may process by the method of wrapping the resin formulation processed into the sheet form or the string form around the crop, stretching over the vicinity of the crop, and laying on the stock soil.

When the harmful arthropod control agent of the present invention is used for controlling harmful arthropods that live in the house (for example, flies, mosquitoes, cockroaches, etc.), The amount of the compound of the present invention is usually 0.01 to 1000 mg per area of 1 m ² , and the amount of the compound of the present invention is usually 0.01 to 500 mg per 1 m ^{3 of} processing space when treated in space. When the harmful arthropod control agent of the present invention is formulated into an emulsion, a wettable powder, a flowable agent, etc., it is usually diluted with water so that the active ingredient concentration is 0.1 to 1000 ppm. The oil agent, aerosol agent, smoke agent, poison bait and the like may be applied as they are.

  The harmful arthropod control agent of the present invention includes other harmful arthropod control agents, nematicides, fungicides, herbicides, plant growth regulators, synergists, fertilizers, soil conditioners, animal feeds. Etc. may be contained.

  Examples of the active ingredients of the other harmful arthropod control agents, acaricides, and nematicides include the following.

(1) Organophosphorous compounds Acephate, Aluminum phosphide, Butathiofos, Cadosafos, Chlorethoxyfos, Chlorfenvinphos, Chlorpyrifos, Chlorpyrifos, Chlorpyrifos-methyl, cyanophos (CYAP), diazinon, DCIP (dichlorodiisopropyl ether), dichlorfenthion (ECP), dichlorvos (DDVP), dimethoate, dimethylvinphos (dimethylvinphos) ), Disulfoton, EPN, ethion, ethoprophos, etrimfos, fenthion (MPP), fenitrothion (MEP), fosthiazate, formimothion (Formothion), hydrogen phosphide, isofenphos, isoxathion, malathion, mesulfenfos, methidathion (DMTP), monocrotophos, nared (BRP) ), Oxydeprofos (ESP), parathion, phosalone, phosmet (PMP), pirimiphos-methyl, pyridafenthion, quinalphos, phenthoate (PAP) ), Profenofos, propaphos, prothiofos, prothiofos, pyraclorfos, salithion, sulprofos, tebupirimfos, temephos, tetrachlorbinphos (tetrachor) vinphos, terbufos, thiometon, trichlorphon (DEP), bamidothion, etc.

(2) Carbamate compounds alaniccarb, bendiocarb, benfuracarb, BPMC, carbaryl, carbofuran, carbosulfan, cloethocarb, ethiofencarb (ethiofencarb) ), Fenobucarb, fenothiocarb, fenoxycarb, furathiocarb, isoprocarb (MIPC), metolcarb, metomyl, methiocarb, NAC, oxamyl (amyl) ), Pirimicarb, propoxur (PHC), XMC, thiodicarb, xylylcarb and the like.

(3) Synthetic pyrethroid compounds acrinathrin, allethrin, benfluthrin, beta-cyfluthrin, bifenthrin, cycloprothrin, cyfluthrin, cyhalothrin (cyfluthrin) cyhalothrin), cypermethrin, deltamethrin, esfenvalerate, ethofenprox, fenpropathrin, fenvalerate, flucythrinate, flufenthrinate Prox (flufenoprox), flumethrin, fluvalinate, halfenprox (halfenprox), imiprothrin, permethrin, praretrin (pi) Threin (pyrethrins), resmethrin, sigma-cypermethrin, silafluofen, tefluthrin, tralomethrin, transfluthrin, 2,3,5,6-tetra Fluoro-4- (methoxymethyl) benzyl (EZ)-(1RS, 3RS; 1RS, 3SR) -2,2-dimethyl-3-prop-1-enylcyclopropanecarboxylate, 2,3,5,6-tetra Fluoro-4-methylbenzyl (EZ)-(1RS, 3RS; 1RS, 3SR) -2,2-dimethyl-3-prop-1-enylcyclopropanecarboxylate, 2,3,5,6-tetrafluoro-4 -(Methoxymethyl) benzyl (1RS, 3RS; 1RS, 3SR) -2,2-dimethyl-3- (2- Chill-1-propenyl) cyclopropanecarboxylate and the like.

(4) Nereistoxin compounds Cartap, bensu1tap, thiocyclam, monosultap, bisultap and the like.

(5) Neonicotinoid compounds Imidacloprid (imidac1oprid), nitenpyram (nitenpyram), acetamiprid (acetamiprid), thiamethoxam (thiamethoxam), thiacloprid, dinotefuran, clothianidin and the like.

(6) Benzoylurea compounds chlorfluazuron, bistrifluron, diafenthiuron, diflubenzuron, fluazuron, flucycloxuron, flufenoc Flufenoxuron, hexaflumuron, lufenuron, novaluron, noiflumuron, teflubenzuron, triflumuron, etc.

(7) Phenylpyrazole compounds Acetoprole, ethiprole, fipronil, vaniliprole, pyriprole, pyrafluprole and the like.

(8) Bt toxin insecticides: live spores and produced crystal toxins derived from Bacillus thuringiensis, and mixtures thereof.

(9) Hydrazine compounds Chromafenozide, halofenozide, methoxyfenozide, tebufenozide and the like.

(10) Organochlorine compounds Aldrin, dieldrin, dienochlor, endosulfan, methoxychlor and the like.

(11) Natural insecticide machine oil, nicotine-sulfate, etc.

(12) Other insecticides avermectin-aver (B), bromopropylate, buprofezin, chlorphenapyr, cyromazine, DD (1,3-Dichloropropene), emamectin benzoate ( emamectin-benzoate, fenazaquin, flupyrazofos, hydroprene, indoxacarb, indoxacarb, metoxadiazone, milbemycin-A, pymetrozine, pyridalyl , Pyriproxyfen, spinosad, sulfluramid, chlorantraniliprole, tolfenpyrad, triazamate, flubendiamide, SI-00 09, cyflumetofen, arsenic acid, benclothiaz, calcium cyanamide, calcium polysulfide, chlordane, DDT, DSP, flufenerim ), Flonicamid, flurimfen, formetanate, lepimectin, metam-ammonium, metam-sodium, methyl bromide Nidinotefuran, potassium oleate, protrifenbute, spiromesifen, sulfur, metaflumizone, spirotetramat, etc.

Acaricides acequinocyl, amitraz, benzoximate, bromopropylate, chinomethionat, chlorobenzilate, CPCBS (chlorfenson), clofentezine ), Kelsen (dicofol), etoxazole, fenbutatin oxide, phenothiocarb, fenpyroximate, fluacrypyrim, fluproxyfen, hexythiazox, hexythiazox propargite: BPPS, polynactins (polynactins), pyridaben, pyrimidifen, tebufenpyrad, tetradifon, spirodiclof Down (spirodiclofen), amide full Met (amidoflumet), bifenazate (Bifenazate), cyflumetofen (Cyflumetofen) or the like.

Nematicide (nematode active ingredient)
DCIP, fosthiazate, levamisol hydrochloride, methyl isothiocyanate, morantel tartarate, etc.

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

Specific examples of the compound of the present invention are shown below.
The abbreviations used in this specification have the following meanings.
Me: methyl group, Et: ethyl group, ⁿ Pr: propyl group, ⁱ Pr: isopropyl group, ⁿ Bu: butyl group, ⁱ Bu: isobutyl group, ^s Bu: sec-butyl group, ^t Bu: tert-butyl group, Bn: benzyl group, Ph: phenyl group.

式（Ｉ）において、
Ｒはメチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ｓｅｃ−ブチル基、ｔｅｒｔ−ブチル基、ペンチル基、イソペンチル基、ネオペンチル基、ｓｅｃ−ペンチル基、ｔｅｒｔ−ペンチル基、２−メチルブチル基、１，２−ジメチルプロピル基、１−エチルプロピル基、ヘキシル基、３，３−ジメチルブチル基、１，２−ジメチルブチル基、２−メチルペンチル基、３−メチルペンチル基、４−メチルペンチル基、２，２−ジメチルブチル基、２，３−ジメチルブチル基、２−エチルブチル基、１−メチルペンチル基、１，２，２−トリメチルプロピル基、１，３−ジメチルブチル基、１−エチルブチル基、１−エチル−２−メチルプロピル基、へプチル基、１−エチル−２，２−ジメチルプロピル基、１−メチルヘキシル基、２−メチルヘキシル基、３−メチルヘキシル基、４−メチルヘキシル基、５−メチルヘキシル基、１，２−ジメチルペンチル基、１，３−ジメチルペンチル基、１，４−ジメチルペンチル基、２，２−ジメチルペンチル基、２，３−ジメチルペンチル基、２，４−ジメチルペンチル基、３，３−ジメチルペンチル基、３，４−ジメチルペンチル基、４，４−ジメチルペンチル基、１−エチルペンチル基、２−エチルペンチル基、３−エチルペンチル基、１−プロピルブチル基、２−エチル−１−メチルブチル基、１−エチル−２−メチルブチル基、１−エチル−３−メチルブチル基、１−ｔｅｒｔ−ブチルプロピル基、３−エチル−４−メチルブチル基、

In formula (I):
R is methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, sec-pentyl, tert-pentyl, 2 -Methylbutyl, 1,2-dimethylpropyl, 1-ethylpropyl, hexyl, 3,3-dimethylbutyl, 1,2-dimethylbutyl, 2-methylpentyl, 3-methylpentyl, 4 -Methylpentyl group, 2,2-dimethylbutyl group, 2,3-dimethylbutyl group, 2-ethylbutyl group, 1-methylpentyl group, 1,2,2-trimethylpropyl group, 1,3-dimethylbutyl group, 1-ethylbutyl, 1-ethyl-2-methylpropyl, heptyl, 1-ethyl-2,2-dimethylpropyl, 1-methyl Ruhexyl group, 2-methylhexyl group, 3-methylhexyl group, 4-methylhexyl group, 5-methylhexyl group, 1,2-dimethylpentyl group, 1,3-dimethylpentyl group, 1,4-dimethylpentyl group 2,2-dimethylpentyl group, 2,3-dimethylpentyl group, 2,4-dimethylpentyl group, 3,3-dimethylpentyl group, 3,4-dimethylpentyl group, 4,4-dimethylpentyl group, 1 -Ethylpentyl group, 2-ethylpentyl group, 3-ethylpentyl group, 1-propylbutyl group, 2-ethyl-1-methylbutyl group, 1-ethyl-2-methylbutyl group, 1-ethyl-3-methylbutyl group, 1-tert-butylpropyl group, 3-ethyl-4-methylbutyl group,

2-propenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-butenyl group, 2-methyl-2-propenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 2- Methyl-2-butenyl group, 2-methyl-2-butenyl group, 2-methyl-3-butenyl group, 3-methyl-2-butenyl group, 3-methyl-3-butenyl group, 1-methyl-1-butenyl Group, 1-methyl-3-butenyl group, 1,2-dimethyl-2-propenyl group, 1-ethyl-2-propenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group 1-methyl-3-pentenyl group, 1-methyl-4-pentenyl group, 2-methyl-2-pentenyl group, 3-methyl-3-pentenyl group, 3-methyl-4-pentenyl group, 4-methyl- 3-pen Nyl group, 4-methyl-4-pentenyl group, 2-propyl-2-propenyl group, 1-propyl-2-propenyl group, 1,2-dimethyl-2-butenyl group, 1,2-dimethyl-3-butenyl Group, 1,3-dimethyl-2-butenyl group, 1,3-dimethyl-3-butenyl group, 1-ethyl-2-methyl-2-propenyl group, 1- (1-methylethyl) -2-propenyl group 1-ethyl-2-butenyl group, 1-ethyl-3-butenyl group,

2-propynyl group, 1-methyl-2-propynyl group, 1,1-dimethyl-2-propynyl group, 1-ethyl-2-propynyl group, 1-propyl-2-propynyl group, 1- (1-methylethyl ) -2-propynyl group, 2-butynyl group, 1-methyl-2-butynyl group, 1-ethyl-2-butynyl group, 2-pentynyl group, 1-methyl-2-pentynyl group, 2-hexynyl group, 3 -Butynyl group, 1-methyl-3-butynyl group, 1-ethyl-3-butynyl group, 3-pentynyl group, 1-methyl-3-pentynyl group, 3-hexynyl group, 4-pentynyl group, 5-hexynyl group ,

2-fluoroethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, 3-fluoropropyl group, 3,3-difluoropropyl group, 3,3,3-trifluoropropyl group, 2,2,3,3-tetrafluoropropyl group, 2,2,3,3,3-pentafluoropropyl group, 1-methyl-2-fluoroethyl group, 1-methyl-2,2,2-trifluoro Ethyl group, 2-fluoro-1- (fluoromethyl) ethyl group, 2,2,2-trifluoro-1- (trifluoromethyl) ethyl group, 4-fluorobutyl group, 4,4-difluorobutyl group, 4 , 4,4-trifluorobutyl group, 3,3,4,4,4-pentafluorobutyl group, 2,2,3,3,4,4-hexafluorobutyl group, 2,2,3,3 4,4,4-heptafluo Butyl group, 1-trifluoromethyl-propyl group, 3,3,3-trifluoro-1-methylpropyl group, 2,2,3,3-tetrafluoro-1-methylpropyl group, 2,2,3, 3,3-pentafluoro-1-methylpropyl group, 2,2,3,3,3-pentafluoro-1-trifluoromethyl-propyl group, 5-fluoropentyl group, 5,5,5-trifluoropentyl Group, 6-fluorohexyl group, 6,6,6-trifluorohexyl group, 2,2,3,4,4-pentafluoro-3-butenyl group, 2,2,3,3,3-pentafluoro- 1-methylpropyl group, 2,2,3,3,4,4,4-heptafluorobutyl group, 2-chloroethyl group, 2,2-dichloroethyl group, 2,2,2-trichloroethyl group, 3- Chloropropyl group, 2- Lolopropyl group, 3-chloro-2,2-dimethylpropyl group, 3,3-dichloropropyl group, 2,3-dichloropropyl group, 2-chloro-1-methylethyl group, 2-chloro-1- (chloromethyl) ) Ethyl group, 1-methyl-2,2,2-trichloroethyl group, 4-chlorobutyl group, 1-chlorobutyl group, 3-chloro-1- (chloromethyl) propyl group, 2-chloro-2-methylpropyl group 5-chloropentyl group, 6-chlorohexyl group, 2-bromoethyl group, 2,2,2-tribromoethyl group, 3-bromopropyl group, 2,3-dibromopropyl group, 2-bromo-1- Methyl ethyl group, 2-bromo-1- (bromomethyl) ethyl group, 4-bromobutyl group, 3-bromo-1- (bromomethyl) propyl group, 2- (bromomethyl) propyl group, 3 -Bromo-2- (bromomethyl) propyl group, 2-iodoethyl group, 3-iodopropyl group,

3-fluoro-2-propenyl group, 2-fluoro-2-propenyl group, 3,3-difluoro-2-propenyl group, 2,3-difluoro-2-propenyl group, 2,3,3-trifluoro-2 -Propenyl group, 4,4-difluoro-3-butenyl group, 3,4,4-trifluoro-3-butenyl group, 2,3-difluoro-2-butenyl group, 2-fluoro-3-methyl-2- Butenyl group, 5,5-difluoro-4-pentenyl group, 4,5,5-trifluoro-4-pentenyl group, 4,4,4-trifluoro-3- (trifluoromethyl) -2-butenyl group, 2,4,4,4-tetrafluoro-2-butenyl group, 4,4,4-trifluoro-3-methyl-2-butenyl group, 4,4,4-trifluoro-3- (trifluoromethyl) 2-butenyl group, 3 Chloro-2-propenyl group, 2-chloro-2-propenyl group, 3,3-dichloro-2-propenyl group, 2,3-dichloro-2-propenyl group, 2,3,3-trichloro-2-propenyl group 4-chloro-3-butenyl group, 4,4-dichloro-3-butenyl group, 3,4-dichloro-3-butenyl group, 3-chloro-2-butenyl group, 2-chloro-2-butenyl group, 2,3-dichloro-2-butenyl group, 2-chloro-3-methyl-2-butenyl group, 5-chloro-4-pentenyl group, 4-chloro-4-pentenyl group, 4,5-dichloro-4- Pentenyl group, 3-bromo-2-propenyl group, 2-bromo-2-propenyl group, 3,3-dibromo-2-propenyl group, 2,3-dibromo-2-propenyl group, 4-bromo-3-butenyl Group 4,4-dibu Mo-3-butenyl group, 3,4-dibromo-3-butenyl group, 3,4,4-tribromo-3-butenyl group, 3-bromo-2-butenyl group, 2-bromo-2-butenyl group, 2 , 3-Dibromo-2-butenyl group, 2-bromo-3-methyl-2-butenyl group, 4-bromo-4-pentenyl group, 4,5-dibromo-4-pentenyl group, 4,5,5-tribromo -4-pentenyl group,

3-chloro-propynyl group, 3-chloro-1-methyl-2-propynyl group, 3-chloro-1,1-dimethyl-2-propynyl group, 3-chloro-1-ethyl-2-propynyl group, 3- Chloro-1-propyl-2-propynyl group, 3-chloro-1- (1-methylethyl) -2-propynyl group, 4-chloro-3-butynyl group, 4-chloro-1-methyl-3-butynyl group 4-chloro-1-ethyl-3-butynyl group, 5-chloro-4-pentynyl group, 6-chloro-5-hexynyl group, 3-bromopropynyl group, 3-bromo-1-methyl-2-propynyl group, 3-bromo 1,1-dimethyl-2-propynyl group, 3-bromo 1-ethyl-2-propynyl group, 3-bromo 1-propyl-2-propynyl group, 3-bromo 1-isopropyl-2-propynyl group, 4 Bromo-3-butynyl group, 4-bromo-1-methyl-3-butynyl group, 4-bromo-1-ethyl-3-butynyl group, 5-bromo-4-pentynyl group, 6-bromo 5-hexynyl group,

で示されるいずれかの基、 Methoxymethyl group, 2-methoxyethyl group, 2-methoxy-1-methylethyl group, 2-methoxy-2-methylethyl group, 2-ethyl-2-methoxyethyl group, 2-ethoxyethyl group, 2-propoxyethyl Group, 2- (1-methylethyl) oxyethyl group, 2-butoxyethyl group, 2-isobutoxyethyl group, 2- (sec-butoxy) ethyl group, 2- (tert-butoxy) ethyl group, 3-methoxypropyl Group, 3-methoxy-3-methylpropyl group, 3-methoxy-3,3-dimethylpropyl group, 3-ethoxypropyl group, 3-propoxypropyl group, 3- (1-methylethyl) oxypropyl group, 3- Butoxypropyl group, 3-isobutoxypropyl group, 3- (sec-butoxy) propyl group, 3- (tert-butoxy) propyl group, , 3-diethoxy-propyl, 2,2-diethoxyethyl group, the following formula

Any of the groups represented by

Methylthiomethyl group, 2-methylthioethyl group, 2-ethylthioethyl group, 2-propylthioethyl group, 2-isopropylthioethyl group, 2-butylthioethyl group, 2-isobutylthioethyl group, 2- (sec- Butylthio) ethyl group, 2- (tert-butylthio) ethyl group, 3-methylthiopropyl group, 3-ethylthiopropyl group, 3-propylthiopropyl group, 3-butylthiobutyl group, 3- (tert-butylthio) propyl Group,

Formylmethyl group, 1-formylethyl group, 2-formylethyl group, 3-formylpropyl group, 4-formylbutyl group, 5-formylpentyl group,

Cyanomethyl group, 1-cyanoethyl group, 2-cyanoethyl group, 3-cyanopropyl group, 4-cyanobutyl group, 5-cyanopentyl group,

1-hydroxyiminoethyl group, 2-hydroxyiminoethyl group, 3-hydroxyiminopropyl group, 4-hydroxyiminobutyl group, 5- (hydroxyimino) pentyl group, 6- (hydroxyimino) hexyl group,

2- (methoxyimino) ethyl group, 2- (ethoxyimino) ethyl group, 2- (propoxyimino) ethyl group, 2- (isopropoxyimino) ethyl group, 3- (methoxyimino) propyl group, 3- (ethoxy Imino) propyl group, 3- (propoxyimino) propyl group, 3- (isopropoxyimino) propyl group, 4- (methoxyimino) butyl group, 4- (ethoxyimino) butyl group, 4- (propoxyimino) butyl group , 4- (isopropoxyimino) butyl group,

2- (methylamino) ethyl group, 3- (methylamino) propyl group, 4- (methylamino) butyl group, 5- (methylamino) pentyl group, 6- (methylamino) hexyl group, 2- (dimethylamino) ) Ethyl group, 3- (dimethylamino) propyl group, 4- (dimethylamino) butyl group, 5- (dimethylamino) pentyl group, 6- (dimethylamino) hexyl group,

2- (methoxycarbonyl) ethyl group, 2- (ethoxycarbonyl) ethyl group, 3- (methoxycarbonyl) propyl group, 3- (ethoxycarbonyl) propyl group, 4- (methoxycarbonyl) butyl group, 4- (ethoxycarbonyl) ) Butyl group, 5- (methoxycarbonyl) pentyl group, 5- (ethoxycarbonyl) pentyl group,

で示されるいずれかの基、 1-hydroxyethyl group, 2-hydroxyethyl group, 3-hydroxypropyl group, 4-hydroxybutyl group, 5-hydroxypentyl group, 6-hydroxyhexyl group, the following formula (corrected in the figure)

Any of the groups represented by

Acetylmethyl group, propionylmethyl group, butyrylmethyl group, valerylmethyl group, 2-acetylethyl group, 2-propionylethyl group, 2-butyrylethyl group, 3-acetylpropyl group, 3-propionylpropyl group, 4-acetylbutyl group,

で示されるいずれかの基、 2- (methoxymethoxy) ethyl group, the following formula

Any of the groups represented by

で示されるいずれかの基、 The following formula

Any of the groups represented by

3- (2,2,2-ethoxy) propyl group, 2- (2-fluoroethoxy) ethyl group, 2- (2-chloroethoxy) ethyl group, 2- (2-bromoethoxy) ethyl group, 2- ( 2-iodoethoxy) ethyl group, 2- (2,2,2-trifluoroethoxy) ethyl group, 3- (2-chloroethoxy) propyl group, 3- (2-bromoethoxy) propyl group, 3- (2 -Iodoethoxy) propyl group, 3- (2,2,2-trifluoroethoxy) propyl group,

で示されるいずれかの基、 The following formula

Any of the groups represented by

で示されるいずれかの基、 The following formula

Any of the groups represented by

で示されるいずれかの基、 The following formula

Any of the groups represented by

で示されるいずれかの基、 The following formula

Any of the groups represented by

Propionyl group, butyryl group, isobutyryl group, valeryl group, isovaleryl group, pivaloyl group,

Cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, 2-methylcyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 1-vinylcyclohexyl group, 1 -Allylcyclohexyl group, 1-ethynylcyclohexyl group, 2-chlorocyclohexyl group, 4-chlorocyclohexyl group, 2-fluorocyclohexyl group, 2-methoxycyclobutyl group, 2-methoxycyclopentyl group, 3-methoxycyclopentyl Group, 2-methoxycyclohexyl group, 3-methoxycyclohexyl group, 4-methoxycyclohexyl group, 2-methoxycycloheptyl group, 2-methoxycyclooctyl group,

で示されるいずれかの基、 The following formula

Any of the groups represented by

で示されるいずれかの基、 Phenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2,3-difluorophenyl group, 2,4-difluorophenyl group, 2,5-difluorophenyl group, 2,6-difluoro Phenyl group, 3,4-difluorophenyl group, 3,5-difluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, 2,3-dichlorophenyl group, 2,4 dichlorophenyl group, 2,5 -Dichlorophenyl group, 2,6-dichlorophenyl group, 3,4-dichlorophenyl group, 3,5-dichlorophenyl group, 2-bromophenyl group, 3-bromophenyl group, 4-bromophenyl group, 2,3-dibromophenyl group 2,4 dibromophenyl group, 2,5-dibromophenyl group, 2,6-dibromophenyl Group, 3,4-dibromophenyl group, 3,5-dibromophenyl group, 2-iodophenyl group, 3-iodophenyl group, 4-iodophenyl group, 2-methylphenyl group, 3-methylphenyl group, 4- Methylphenyl group, 2,3-dimethylphenyl group, 2,4 dimethylphenyl group, 2,5-dimethylphenyl group, 2,6-dimethylphenyl group, 3,4-dimethylphenyl group, 3,5-dimethylphenyl group 2-methoxyphenyl group, 3-methoxyphenyl group, 4-methoxyphenyl group, 2,3-dimethoxyphenyl group, 2,4 dimethoxyphenyl group, 2,5-dimethoxyphenyl group, 2,6-dimethoxyphenyl group, 3,4-dimethoxyphenyl group, 3,5-dimethoxyphenyl group, 2-ethylphenyl group, 3-ethylphenyl group, 4-ethylphenyl group Nyl group, 2- (trifluoromethyl) phenyl group, 3- (trifluoromethyl) phenyl group, 4- (trifluoromethyl) phenyl group, 2-methylthiophenyl group, 3-methylthiophenyl group, 4-methylthiophenyl group 2- (trifluoromethoxy) phenyl group, 3- (trifluoromethoxy) phenyl group, 4- (trifluoromethoxy) phenyl group, 2-nitrophenyl group, 3-nitrophenyl group, 4-nitrophenyl group, 2 -Cyanophenyl group, 3-cyanophenyl group, 4-cyanophenyl group, the following formula

Any of the groups represented by

で示されるいずれかの基、下記の式

で示されるいずれかの基、下記の式

で示されるいずれかの基、下記の式

で示されるいずれかの基、 The following formula

Any of the groups represented by

Any of the groups represented by

Any of the groups represented by

Any of the groups represented by

で示されるいずれかの基、下記の式

で示されるいずれかの基、 The following formula

Any of the groups represented by

Any of the groups represented by

で示されるいずれかの基、下記の式

で示されるいずれかの基、 The following formula

Any of the groups represented by

Any of the groups represented by

で示されるいずれかの基、２−ピリジル基、３−ピリジル基、４−ピリジル基、２−ピリミジニル基、４−ピリミジニル基、５−ピリミジニル基、２−ピラジニル基、３−ピリダジニル基、４−ピリダジニル基、下記の式

で示されるいずれかの基、下記の式

で示されるいずれかの基、 The following formula

2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 2-pyrimidinyl group, 4-pyrimidinyl group, 5-pyrimidinyl group, 2-pyrazinyl group, 3-pyridazinyl group, 4- Pyridazinyl group, the following formula

Any of the groups represented by

Any of the groups represented by

で示されるいずれかの基、下記の式

で示されるいずれかの基、下記の式

で示されるいずれかの基、 The following formula

Any of the groups represented by

Any of the groups represented by

Any of the groups represented by

で示されるいずれかの基、 The following formula

Any of the groups represented by

で示されるいずれかの基、 The following formula

Any of the groups represented by

Benzyl group, 2-fluorobenzyl group, 3-fluorobenzyl group, 4-fluorobenzyl group, 2,3-difluorobenzyl group, 2,4-difluorobenzyl group, 2,5-difluorobenzyl group, 2,6-difluoro Benzyl group, 3,4-difluorobenzyl group, 3,5-difluorobenzyl group, 2-chlorobenzyl group, 3-chlorobenzyl group, 4-chlorobenzyl group, 2,3-dichlorobenzyl group, 2,4-dichloro Benzyl group, 2,5-dichlorobenzyl group, 2,6-dichlorobenzyl group, 3,4-dichlorobenzyl group, 3,5-dichlorobenzyl group, 2-bromobenzyl group, 3-bromobenzyl group, 4-bromo Benzyl group, 2,3-dibromobenzyl group, 2,4-dibromobenzyl group, 2,5-dibromobenzyl group, 2,6-dibromobenzyl group Gyl group, 3,4-dibromobenzyl group, 3,5-dibromobenzyl group, 2-iodobenzyl group, 3-iodobenzyl group, 4-iodobenzyl group, 2-methylbenzyl group, 3-methylbenzyl group, 4 -Methylbenzyl group, 2- (trifluoromethyl) benzyl group, 3- (trifluoromethyl) benzyl group, 4- (trifluoromethyl) benzyl group, 2-methoxybenzyl group, 3-methoxybenzyl group, 4-methoxy Benzyl group, 2,5-dimethoxybenzyl group, 3,5-dimethoxybenzyl group, 2-methylthiobenzyl group, 3-methylthiobenzyl group, 4-methylthiobenzyl group, 2- (trifluoromethoxy) benzyl group, 3- ( Trifluoromethoxy) benzyl group, 4- (trifluoromethoxy) benzyl group, 2-nitrobenzyl group, 3 Nitrobenzyl group, 4-nitrobenzyl group, 2-cyanobenzyl group, 3-cyanobenzyl group, 4-cyanobenzyl group, 2-ethoxy-benzyl group, 3-ethoxybenzyl group, 4-ethoxybenzyl group, 4-isopropyl Benzyl group, 4-tert-butylbenzyl group, 2-fluoro-4- (trifluoromethyl) benzyl group, 2-fluoro-5- (trifluoromethyl) benzyl group, 4-fluoro-3- (trifluoromethyl) Benzyl group, 2,4-bis (trifluoromethyl) benzyl group, 5-fluoro-2-methylbenzyl group, pentafluorobenzyl group, phenethyl group,

で示されるいずれかの基、下記の式

The following formula

Any of the groups represented by

で示されるいずれかの基、下記の式

Any of the groups represented by

で示されるいずれかの基、下記の式

で示されるいずれかの基、

Any of the groups represented by

Any of the groups represented by

で示されるいずれかの基、下記の式

で示されるいずれかの基、 The following formula

Any of the groups represented by

Any of the groups represented by

で示されるいずれかの基、下記の式

で示されるいずれかの基、 The following formula

Any of the groups represented by

Any of the groups represented by

で示されるいずれかの基、下記の式

で示されるいずれかの基、下記の式

で示されるいずれかの基、下記の式

で示されるいずれかの基、下記の式

で示されるいずれかの基、下記の式

で示されるいずれかの基、下記の式

で示されるいずれかの基、 The following formula

Any of the groups represented by

Any of the groups represented by

Any of the groups represented by

Any of the groups represented by

Any of the groups represented by

Any of the groups represented by

Any of the groups represented by

で示されるいずれかの基、下記の式

で示されるいずれかの基、下記の式

で示されるいずれかの基、下記の式

で示されるいずれかの基、 The following formula

Any of the groups represented by

Any of the groups represented by

Any of the groups represented by

Any of the groups represented by

2-phenyloxyethyl group, 2- (2-fluorophenyloxy) ethyl group, 2- (3-fluorophenyloxy) ethyl group, 2- (4-fluorophenyloxy) ethyl group, 2- (2,3- Difluorophenyloxy) ethyl group, 2- (2,4-difluorophenyloxy) ethyl group, 2- (2,5-difluorophenyloxy) ethyl group, 2- (2,6-difluorophenyloxy) ethyl group, 2 -(3,4-difluorophenyloxy) ethyl group, 2- (3,5-difluorophenyloxy) ethyl group, 2- (2-chlorophenyloxy) ethyl group, 2- (3-chlorophenyloxy) ethyl group, 2 -(4-chlorophenyloxy) ethyl group, 2- (2,3-dichlorophenyloxy) ethyl group, 2- (2,4dichlorophenyloxy) ) Ethyl group, 2- (2,5-dichlorophenyloxy) ethyl group, 2- (2,6-dichlorophenyloxy) ethyl group, 2- (3,4-dichlorophenyloxy) ethyl group, 2- (3,5- Dichlorophenyloxy) ethyl group, 2- (2-bromophenyloxy) ethyl group, 2- (3-bromophenyloxy) ethyl group, 2- (4-bromophenyloxy) ethyl group, 2- (2,3-dibromo) Phenyloxy) ethyl group, 2- (2,4dibromophenyloxy) ethyl group, 2- (2,5-dibromophenyloxy) ethyl group, 2- (2,6-dibromophenyloxy) ethyl group, 2- ( 3,4-dibromophenyloxy) ethyl group, 2- (3,5-dibromophenyloxy) ethyl group, 2- (2-iodophenyloxy) ethyl group, 2- ( -Iodophenyloxy) ethyl group, 2- (4-iodophenyloxy) ethyl group, 2- (2-methylphenyloxy) ethyl group, 2- (3-methylphenyloxy) ethyl group, 2- (4-methyl) Phenyloxy) ethyl group, 2- (2,3-dimethylphenyloxy) ethyl group, 2- (2,4dimethylphenyloxy) ethyl group, 2- (2,5-dimethylphenyloxy) ethyl group, 2- ( 2,6-dimethylphenyloxy) ethyl group, 2- (3,4-dimethylphenyloxy) ethyl group, 2- (3,5-dimethylphenyloxy) ethyl group, 2- (2-methoxyphenyloxy) ethyl group 2- (3-methoxyphenyloxy) ethyl group, 2- (4-methoxyphenyloxy) ethyl group, 2- (2,3-dimethoxyphenyloxy) ethyl Group, 2- (2,4 dimethoxyphenyloxy) ethyl group, 2- (2,5-dimethoxyphenyloxy) ethyl group, 2- (2,6-dimethoxyphenyloxy) ethyl group, 2- (3,4- Dimethoxyphenyloxy) ethyl group, 2- (3,5-dimethoxyphenyloxy) ethyl group, 2- (2-ethylphenyloxy) ethyl group, 2- (3-ethylphenyloxy) ethyl group, 2- (4- Ethyl group, 2- (2- (trifluoromethyl) phenyloxy) ethyl group, 2- (3- (trifluoromethyl) phenyloxy) ethyl group, 2- (4- (trifluoromethyl) phenyl Oxy) ethyl group, 2- (2-methylthiophenyloxy) ethyl group, 2- (3-methylthiophenyloxy) ethyl group, 2- (4-methylthiooff) Nyloxy) ethyl group, 2- (2- (trifluoromethoxy) phenyloxy) ethyl group, 2- (3- (trifluoromethoxy) phenyloxy) ethyl group, 2- (4- (trifluoromethoxy) phenyloxy) Ethyl group, 2- (2-nitrophenyloxy) ethyl group, 2- (3-nitrophenyloxy) ethyl group, 2- (4-nitrophenyloxy) ethyl group, 2- (2-cyanophenyloxy) ethyl group 2- (3-cyanophenyloxy) ethyl group, 2- (4-cyanophenyloxy) ethyl group, 3-phenyloxypropyl group,

2-benzyloxyethyl group, 2- (2-fluorobenzyloxy) ethyl group, 2- (3-fluorobenzyloxy) ethyl, 2- (4-fluorobenzyloxy) ethyl group, 2- (2,3-difluoro Benzyloxy) ethyl group, 2- (2,4-difluorobenzyloxy) ethyl group, 2- (2,5-difluorobenzyloxy) ethyl group, 2- (2,6-difluorobenzyloxy) ethyl group, 2- (3,4-difluorobenzyloxy) ethyl group, 2- (3,5-difluorobenzyloxy) ethyl group, 2- (2-chlorobenzyloxy) ethyl group, 2- (3-chlorobenzyloxy) ethyl group, 2- (4-chlorobenzyloxy) ethyl group, 2- (2,3-dichlorobenzyloxy) ethyl group, 2- (2,4-dichlorobenzyloxy) ) Ethyl group, 2- (2,5-dichlorobenzyloxy) ethyl group, 2- (2,6-dichlorobenzyloxy) ethyl group, 2- (3,4-dichlorobenzyloxy) ethyl group, 2- (3 , 5-dichlorobenzyloxy) ethyl group, 2- (2-bromobenzyloxy) ethyl group, 2- (3-bromobenzyloxy) ethyl group, 2- (4-bromobenzyloxy) ethyl group, 2- (2 , 3-Dibromobenzyloxy) ethyl group, 2- (2,4-dibromobenzyloxy) ethyl group, 2- (2,5-dibromobenzyloxy) ethyl group, 2- (2,6-dibromobenzyloxy) ethyl Group, 2- (3,4-dibromobenzyloxy) ethyl group, 2- (3,5-dibromobenzyloxy) ethyl group, 2- (2-iodobenzyloxy) ethyl group, 2- 3-iodobenzyloxy) ethyl group, 2- (4-iodobenzyloxy) ethyl group, 2- (2-methylbenzyloxy) ethyl group, 2- (3-methylbenzyloxy) ethyl group, 2- (4- Methylbenzyloxy) ethyl group, 2- (2- (trifluoromethyl) benzyloxy) ethyl group, 2- (3- (trifluoromethyl) benzyloxy) ethyl group, 2- (4- (trifluoromethyl) benzyl Oxy) ethyl group, 2- (2-methoxybenzyloxy) ethyl group, 2- (3-methoxybenzyloxy) ethyl group, 2- (4-methoxybenzyloxy) ethyl group, 2- (2,5-dimethoxybenzyl) Oxy) ethyl group, 2- (3,5-dimethoxybenzyloxy) ethyl group, 2- (2-methylthiobenzyloxy) ethyl group, 2- (3- Methylthiobenzyloxy) ethyl group, 2- (4-methylthiobenzyloxy) ethyl group, 2- (2- (trifluoromethoxy) benzyloxy) ethyl group, 2- (3- (trifluoromethoxy) benzyloxy) ethyl group 2- (4- (trifluoromethoxy) benzyloxy) ethyl group, 2- (2-nitrobenzyloxy) ethyl group, 2- (3-nitrobenzyloxy) ethyl group, 2- (4-nitrobenzyloxy) Ethyl group, 2- (2-cyanobenzyloxy) ethyl group, 2- (3-cyanobenzyloxy) ethyl group, 2- (4-cyanobenzyloxy) ethyl group, 2- (2-ethoxy-benzyloxy) ethyl Group, 2- (3-ethoxybenzyloxy) ethyl group, 2- (4-ethoxybenzyloxy) ethyl group, 2- (4-isopropyl Rubenzyloxy) ethyl group, 2- (4-tert-butylbenzyloxy) ethyl group, 2- (2-fluoro-4- (trifluoromethyl) benzyloxy) ethyl group, 2- (2-fluoro-5- (Trifluoromethyl) benzyloxy) ethyl group, 2- (4-fluoro-3- (trifluoromethyl) benzyloxy) ethyl group, 2- (2,4-bis (trifluoromethyl) benzyloxy) ethyl group, 2- (5-fluoro-2-methylbenzyloxy) ethyl group, 2- (pentafluorobenzyloxy) ethyl group, or 3-benzyloxypropyl group.

で示される化合物２．５ｇを加え、２時間攪拌した後、室温で一昼夜放置した。その後、反応混合物に飽和塩化アンモニウム水溶液を加え、クロロホルムで抽出した。有機層を硫酸ナトリウムで乾燥した後、減圧下濃縮した。残渣をヘキサンに溶解し、不溶物をろ別した後、減圧下濃縮した。残渣をシリカゲルカラムクロマトグラフィーに付して、式（１）

で示される化合物（以下、本発明化合物（１）と記す。）０．８９ｇを含む粗生成物を得た。
¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）δ（ｐｐｍ）：４．５４（４Ｈ，ｑ，Ｊ＝７Ｈｚ），１．４６（６Ｈ，ｔ，Ｊ＝７Ｈｚ）． Next, production examples of the compound of the present invention are shown.
Production Example 1
8.4 g of a 20% ethanol solution of sodium ethoxide was dissolved in 25 ml of tetrahydrofuran, and the formula (a) was added under ice cooling.

After adding 2.5 g of the compound represented by formula (2) and stirring for 2 hours, the mixture was allowed to stand overnight at room temperature. Thereafter, a saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was dissolved in hexane, insolubles were filtered off, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain the formula (1)

A crude product containing 0.89 g of a compound represented by the following (hereinafter referred to as the present compound (1)) was obtained.
¹ H-NMR (CDCl ₃ , TMS) δ (ppm): 4.54 (4H, q, J = 7 Hz), 1.46 (6H, t, J = 7 Hz).

で示される化合物（以下、本発明化合物（２）と記す。）０．２１ｇを得た。
¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：４．４３（４Ｈ，ｔ，Ｊ＝７Ｈｚ），１．８９−１．８０（４Ｈ，ｍ），１．０２（６Ｈ，ｔ，Ｊ＝７Ｈｚ）． Production Example 2
Under ice cooling, 0.39 g (60% oily) of sodium hydride was added to 10 ml of 1-propanol and stirred for 30 minutes. To the reaction mixture, 1.0 g of the compound represented by the formula (a) was added and stirred for 1 hour, and then left at room temperature for a whole day and night. Thereafter, a saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was dissolved in t-butyl methyl ether, insolubles were filtered off, and concentrated under reduced pressure. The residue was subjected to silica gel preparative thin layer chromatography to obtain the formula (2)

0.21 g of a compound represented by the following (hereinafter referred to as the present compound (2)) was obtained.
¹ H-NMR (CDCl ₃ , TMS): 4.43 (4H, t, J = 7 Hz), 1.89-1.80 (4H, m), 1.02 (6H, t, J = 7 Hz).

で示される化合物（以下、本発明化合物（３）と記す。）１００ｍｇを含む粗生成物を得た。
¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）δ（ｐｐｍ）：５．２３−５．１３（２Ｈ，ｍ），１．４３（１２Ｈ，ｄ，Ｊ＝６Ｈｚ）． Production Example 3
Under ice cooling, 120 mg (60% oily) of sodium hydride was added to 3.5 ml of 2-propanol and stirred for 30 minutes. To the reaction mixture, 300 mg of the compound represented by the formula (a) was added and stirred for 1 hour, and then stirred at room temperature for 7 hours. Thereafter, 60 mg (60% oily) of sodium hydride and 2 ml of 2-propanol were further added, and the mixture was allowed to stand overnight at room temperature. Thereafter, a saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was dissolved in hexane, insolubles were filtered off, and concentrated under reduced pressure. The residue was subjected to silica gel preparative thin layer chromatography to obtain the formula (3)

A crude product containing 100 mg of a compound represented by the following (hereinafter referred to as the present compound (3)) was obtained.
¹ H-NMR (CDCl ₃ , TMS) δ (ppm): 5.23-5.13 (2H, m), 1.43 (12H, d, J = 6 Hz).

で示される化合物（以下、本発明化合物（４）と記す。）１１０ｍｇを含む粗生成物を得た。
¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）δ（ｐｐｍ）：４．５６−４．４８（６Ｈ，ｍ），４．１６−４．１２（２Ｈ，ｍ），３．８５−３．８１（２Ｈ，ｍ），１．４５（６Ｈ，ｓ），１．３９（６Ｈ，ｓ）． Production Example 4
Under ice-cooling, 120 mg (60% oily) of sodium hydride was added to 2 ml of 2,2-dimethyl-1,3-dioxolane-4-methanol and stirred for 15 minutes. To the reaction mixture, 300 mg of the compound represented by the formula (a) was added and stirred for 2 hours, and then allowed to stand overnight at room temperature. Thereafter, 60 mg (60% oily) of sodium hydride was further added and stirred for 1 hour. Thereafter, a saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was dissolved in a mixed solvent of hexane and t-butyl methyl ether, washed with water, and the organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to preparative thin layer chromatography on silica gel to obtain the formula (4)

A crude product containing 110 mg of the compound (hereinafter referred to as the present compound (4)) was obtained.
¹ H-NMR (CDCl ₃ , TMS) δ (ppm): 4.56 to 4.48 (6H, m), 4.16 to 4.12 (2H, m), 3.85 to 3.81 (2H) , M), 1.45 (6H, s), 1.39 (6H, s).

で示される化合物（以下、本発明化合物（５）と記す。）２００ｍｇを得た。
¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）δ（ｐｐｍ）：４．９４（２Ｈ，ｑｕｉｎｔ），４．２０（４Ｈ，ｄｄ，Ｊ＝１３，３Ｈｚ），４．０６（４Ｈ，ｄｄ，Ｊ＝１４，３Ｈｚ），１．４８（６Ｈ，ｓ），１．４５（６Ｈ，ｓ）． Production Example 5
500 mg of the compound represented by the formula (a) and 620 mg of 2,2-dimethyl-1,3-dioxane-5-ol are dissolved in 5 ml of tetrahydrofuran, and 200 mg (60% oily) of sodium hydride is added under ice cooling for 2 hours. After stirring, the mixture was left at room temperature for 1 day. Thereafter, 100 mg (60% oily) of sodium hydride was further added and stirred for 1 hour. Thereafter, a saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was dissolved in t-butyl methyl ether, insolubles were filtered off, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain the formula (5)

200 mg (hereinafter referred to as the present compound (5)) was obtained.
¹ H-NMR (CDCl ₃ , TMS) δ (ppm): 4.94 (2H, quint), 4.20 (4H, dd, J = 13, 3 Hz), 4.06 (4H, dd, J = 14 , 3 Hz), 1.48 (6H, s), 1.45 (6H, s).

で示される化合物１３．８ｇ、および炭酸水素ナトリウム３１．５ｇを酢酸エチル１５０ｍｌに懸濁させ、該混合溶液にパークロルメチルメルカプタン１８．２ｇを滴下し室温で一昼夜攪拌した。その後、反応混合物に水を加え、酢酸エチルで抽出した。有機層を飽和炭酸水素ナトリウム水溶液、および飽和塩化ナトリウム水溶液で順次洗浄し、硫酸ナトリウムで乾燥した後、減圧下濃縮した。残渣をシリカゲルカラムクロマトグラフィーに付して、式（ａ）で示される化合物１０．４ｇを得た。
¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）δ（ｐｐｍ）：３．０８（３Ｈ，ｂｒｓ）、３．０５（３Ｈ，ｂｒｓ） Next, the production of the production intermediate of the compound of the present invention is shown as a reference production example.
Reference production example 1
Formula (d-1)

13.8 g and 31.5 g of sodium bicarbonate were suspended in 150 ml of ethyl acetate, 18.2 g of perchlormethyl mercaptan was added dropwise to the mixed solution, and the mixture was stirred at room temperature for a whole day and night. Thereafter, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 10.4 g of the compound represented by the formula (a).
¹ H-NMR (CDCl ₃ , TMS) δ (ppm): 3.08 (3H, brs), 3.05 (3H, brs)

Reference production example 2
10.0 g of N, N-dimethylcarbamoyl chloride and 5.9 g of thiourea were suspended in 100 ml of tetrahydrofuran and heated to reflux for 10 hours. To the mixture, 1.0 g of N, N-dimethylcarbamoyl chloride was further added and heated under reflux for 2 hours. Thereafter, the reaction mixture was cooled to room temperature, and the resulting crystals were filtered off and washed successively with tetrahydrofuran and hexane to obtain 13.8 g of a compound represented by the formula (d-1).
¹ H-NMR (DMSO-d ₆ , TMS) δ (ppm): 9.71 (4H, br), 3.01 (3H, s), 2.99 (3H, s).

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

Formulation Example 1
10 parts of each of the compounds (1) to (5) of the present invention are dissolved in a mixture of 35 parts of xylene and 35 parts of N, N-dimethylformamide, and 14 parts of polyoxyethylene styryl phenyl ether and calcium dodecylbenzenesulfonate 6 Add 10 parts and mix well by stirring to obtain each 10% emulsion.

Formulation Example 2
20 parts of each of the compounds (1) to (5) of the present invention was added to a mixture of 4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, 20 parts of synthetic silicon hydroxide fine powder and 54 parts of diatomaceous earth and stirred well. Mix to obtain each 20% wettable powder.

Formulation Example 3
To 2 parts of each of the compounds (1) to (5) of the present invention, 1 part of a synthetic silicon hydrous fine powder, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65 parts of kaolin clay are mixed sufficiently. Next, an appropriate amount of water is added to these mixtures, and the mixture is further stirred, granulated with a granulator, and dried by ventilation to obtain 2% granules.

Formulation Example 4
1 part of each of the compounds (1) to (5) of the present invention is dissolved in an appropriate amount of acetone, and 5 parts of a synthetic silicon hydroxide fine powder, 0.3 part of PAP and 93.7 parts of Fubasami clay are added to this, and mixed thoroughly. Then, the acetone is removed by evaporation to obtain each 1% powder.

Formulation Example 5
10 parts of each of the compounds (1) to (5) of the present invention; 35 parts of white carbon containing 50 parts of polyoxyethylene alkyl ether sulfate ammonium salt; and 55 parts of water are mixed and finely pulverized by a wet grinding method. Obtain each 10% flowable.

Formulation Example 6
0.1 parts of each of the compounds (1) to (5) of the present invention are dissolved in 5 parts of xylene and 5 parts of trichloroethane and mixed with 89.9 parts of deodorized kerosene to obtain each 0.1% oil. .

Formulation Example 7
10 mg of each of the compounds (1) to (5) of the present invention is dissolved in 0.5 ml of acetone, and this solution is added to 5 g of animal solid feed powder (solid feed powder CE-2 for breeding, product of Nippon Claire Co., Ltd.). Process and mix evenly. The acetone is then evaporated to dryness to obtain each poison bait.

  Next, the harmful arthropod controlling effect of the compound of the present invention is shown by test examples.

Test example 1
Formulations of the present compounds (1) to (4) obtained in Formulation Example 5 were diluted with water so that the active ingredient concentration was 500 ppm to prepare a test spray solution.
On the other hand, a cucumber was planted in a polyethylene cup and allowed to grow until the first true leaf developed, and about 30 cotton aphids were infested there. One day later, the test spray solution was sprayed onto the cucumber at a rate of 20 ml / cup. Six days after spraying, the number of cotton aphids was investigated, and the control value was determined by the following formula.
Control value (%) = {1− (Cb × Tai) / (Cai × Tb)} × 100
In addition, the character in a formula represents the following meaning.
Cb: number of insects before treatment in the untreated group Cai: number of insects when observed in the untreated group Tb: number of insects before treatment in the treated group Tai: number of insects when observed in the treated group As a result, the compound of the present invention (1 ) To (4), the treatment groups of the test spray solution each showed a control value of 90% or more.

Test example 2
Each of the present compounds (1) to (4) was formulated according to Formulation Example 5. This preparation was diluted with water so that the active ingredient concentration was 500 ppm to prepare a test spray solution.
On the other hand, cabbage was planted in a polyethylene cup, grown until the first true leaf developed, the other leaves were excised, leaving the first true leaf, and adult whitefly was released to allow it to lay eggs for about 24 hours. . The cabbage was kept in a greenhouse for 8 days, and the test spray solution was sprayed at a rate of 20 ml / cup in a state where larvae hatched from the laid eggs. Seven days after spraying, the number of surviving larvae on the cabbage leaf was investigated, and the control value was determined by the following formula.
Control value (%) = {1− (Cb × Tai) / (Cai × Tb)} × 100
In addition, the character in a formula represents the following meaning.
Cb: number of insects before treatment in the untreated group Cai: number of insects when observed in the untreated group Tb: number of insects before treatment in the treated group Tai: number of insects when observed in the treated group As a result, the compound of the present invention (1 ) To (4), the treatment groups of the test spray solution each showed a control value of 90% or more.

Test example 3
Each of the present compounds (1) to (3) was formulated according to Formulation Example 5. This preparation was diluted with water so that the concentration of the compound of the present invention was 500 ppm.
On the other hand, about 60 adult spider mites were released on a perennial seedling seedling planted in a plastic cup (7 days after sowing, the primary leaf development stage) and left for 1 day. Each of these seedlings was sprayed with 20 ml of the diluted solution.
Eight days after spraying, the number of surviving ticks on the leaves of the vineyard bean was investigated, and the control rate was calculated by the following formula.
Control rate (%) = 100 × {1− (number of surviving mites in treated area) / (number of surviving mites in untreated area)}
As a result, all the groups which treated each of the compounds (1) to (3) of the present invention had a control rate of 90% or more.

  According to the present invention, the compound of the present invention has an excellent controlling effect on harmful arthropods, and therefore is useful as an active ingredient of a harmful arthropod controlling agent.

Claims (10)

Formula (I)

[Where,
R is a C1-C7 chain hydrocarbon group (provided that the chain hydrocarbon group may be substituted with one or more substituents selected from the following group A), a C3-C6 alkanoyl group, a -Q group , -TQ group, -T-O-Q group, or -T-O-TQ group,
Q is a 3- to 10-membered carbocyclic group (provided that the carbocyclic group may be substituted with one or more substituents selected from the following group B, and substituted with one or more substituents selected from the following group C) Or a 3- to 10-membered heterocyclic group (provided that the heterocyclic group may be substituted with one or more substituents selected from the following group B and selected from the following group C) And may be substituted with one or more substituents.
T represents a C1-C4 alkanediyl group;
A group halogen atom, a cyano group, a nitro ^{group, -Z 2 - (T-Z} 2) r-R 10 ^{group, - (Z 2) p-} C (= O) - (Z 3) q-R 10 group And a group of monovalent substituents consisting of —C (═NO—R ¹⁰ ) —R ¹¹ groups,
Group B is a halogen atom, a cyano group, a nitro group, -R ^{12 group, -Z 2 - (T-Z} 2) r-R 10 ^{group, - (T-Z 2)} s-R 10 group, - (Z ² ) p-C (= O)-(Z ³ ) q-R ¹⁰ group, -C (= NO-R ¹⁰ ) -R ¹¹ group, -Q ¹ group, -Z ² -Q ¹ group, -TQ ¹ represents a group of monovalent substituents consisting of ¹ group, -Z ² -TQ ¹ group, and -TZ ² -Q ¹ group,
Group C represents a group of divalent substituents consisting of an oxygen atom, a sulfur atom, a -T- group, a -Z ⁴ -TZ ⁵ -group, and a -TZ ⁴ -T- group {here ,
r represents 0, 1 or 2, p and q each independently represents 0 or 1, s represents 1 or 2,
Z ² and Z ³ each independently represent an oxygen atom, a sulfur atom, a —NH— group or a —N (C 1 -C 6 alkyl) -group;
Z ⁴ and Z ⁵ each independently represents an oxygen atom or a sulfur atom,
R ¹⁰ and R ¹¹ each independently represent a C1-C7 chain hydrocarbon group which may be substituted with a halogen atom, or a hydrogen atom, and R ¹² may be substituted with a halogen atom. Represents a chain hydrocarbon group,
Q ¹ is a 3- to 10-membered carbocyclic group (provided that the carbocyclic group may be substituted with one or more substituents selected from Group A above, and the same or adjacent ring member atoms from the Group C above) Which may be substituted with one or more selected substituents), or a 3- to 10-membered heterocyclic group (provided that the heterocyclic group is substituted with one or more substituents selected from Group A above). And may be substituted with one or more divalent groups selected from the above group C in the same or adjacent ring atoms. }. ]
A thiadiazole compound represented by In formula (I):
R is C1-C7 chain hydrocarbon group (provided that the C1-C7 chain hydrocarbon group may be substituted with one or more substituents selected from the following group D.), - Q ⁶ group, - A T-Q ⁶ group, a -T-O-Q ⁶ group, or a -T-O-T-Q ⁶ group,
Q ⁶ is a 3- to 6-membered carbocyclic group (provided that the carbocyclic group may be substituted with one or more substituents selected from Group E below, and one or more substituents selected from Group F below) Or a 3 to 6-membered saturated heterocyclic group (provided that the heterocyclic group may be substituted with one or more substituents selected from Group E above, and may be the same or adjacent). And may be substituted with one or more substituents selected from the following group F):
T is a C1-C4 alkanediyl group;
Group D halogen ^{atoms, -Z 2 - (T-Z} 2) r-R 10 group, ^{and, - (Z 2) p-} C (= O) - (Z 3) 1 monovalent consisting q-R ¹⁰ group A group of substituents of
Group E is a halogen atom, -R ^{12 group, -Z 2 - (T-Z} 2) r-R 10 ^{group, - (T-Z 2)} s-R 10 ^{group, - (Z 2) p-} C (= O)-(Z ³ ) q-R ¹⁰ group, -Q ³ group, -Z ² -Q ³ group, -TQ ³ group, -Z ² -TQ ³ group, and -TZ ² A group of monovalent substituents consisting of -Q ¹ groups;
Group F is a group of divalent substituents consisting of an oxygen atom, a -T- group, and a -Z ⁴ -TZ ⁵ -group,
r is 0, 1 or 2, p and q are each independently 0 or 1, s is 1 or 2,
Z ² and Z ³ are each independently an oxygen atom, a sulfur atom, a —NH— group or a —N (C 1 -C 6 alkyl) -group;
Z ⁴ and Z ⁵ are each independently an oxygen atom or a sulfur atom,
Each R ¹⁰ is independently a C1-C7 chain hydrocarbon group optionally substituted with a halogen atom, or a hydrogen atom;
R ¹² is a C1-C7 chain hydrocarbon group which may be substituted with a halogen atom,
The thiadiazole compound according to claim 1, wherein Q ³ is a 3- to 10-membered carbocyclic group or a 3- to 10-membered heterocyclic group. In formula (I):
R is C1-C7 chain hydrocarbon group, -Q ⁷ group or -T-Q ⁷ group,
Q ⁷ is

A group represented by
t is 0 or 1;
The thiadiazole compound according to claim 1, wherein R ¹³ and R ¹⁴ are each independently a hydrogen atom or a C1-C4 alkyl group. In formula (I):
R is a C1-C7 chain hydrocarbon group (provided that the chain hydrocarbon group is selected from the group of substituents consisting of a halogen atom, a cyano group, and a —Z ² — (TZ ² ) r—R ¹⁰ group) The thiadiazole compound according to claim 1, which may be substituted with a group. The thiadiazole compound according to claim 1, wherein in formula (I), R is a C1-C7 chain hydrocarbon group. In formula (I), a -Q ⁷ group or -T-Q ⁷ group,
Q ⁷ is

The thiadiazole compound according to claim 1, wherein t is 0 or 1, and R ¹³ and R ¹⁴ are each independently a hydrogen atom or a C1-C4 alkyl group. In formula (I):
2. R is an ethyl group, a propyl group, an isopropyl group, a 2,2-dimethyl-1,3-dioxolan-4-methyl group, and a 2,2-dimethyl-1,3-dioxane-5-yl group. Thiadiazole compounds. The harmful arthropod control agent which contains the compound in any one of Claims 1-7 as an active ingredient. Use of a compound according to any of claims 1 to 7 for controlling harmful arthropods. A method for controlling harmful arthropods, which comprises applying the compound according to any one of claims 1 to 7 to harmful arthropods or habitats of harmful arthropods.