JP7110190B2 - Nitrogen-containing heterocyclic compound and agricultural and horticultural fungicide containing it as an active ingredient - Google Patents

Description

TECHNICAL FIELD The present invention relates to a nitrogen-containing heterocyclic compound and an agricultural chemical containing the compound as an active ingredient.

Disease control of agricultural and horticultural crops plays an important role in ensuring stable agricultural production. Therefore, various fungicides are used, but long-term use of fungicides leads to the emergence of drug-resistant bacteria. It is

By the way, with respect to 1,5,6-substituted-2-pyrimidinone compounds and 1,5,6-substituted-2-pyrazinone compounds, for example, a heteroaryloxy group at the para-position of the phenyl group at the 6-position as a dopamine D1 ligand 1,5,6-substituted-2-pyrimidinone compounds and 1,5,6-substituted-2-pyrazinone compounds substituted with are disclosed (see, for example, US Pat.

WO2014/207601 WO2014/072881

However, the uses of the compounds described in the specifications of Patent Document 1 and Patent Document 2 are both related to medicine, and are different from the technical field to which the agricultural and horticultural fungicide of the present invention belongs.

An object of the present invention is to provide novel compounds that are effective as agricultural and horticultural fungicides.

In order to solve the above-mentioned problems, the present inventors have extensively studied a group of 1,4,5,6-substituted-2-pyrimidinone compounds and a group of 1,3,5,6-substituted-2-pyrazinone compounds. As a result, with respect to the 6-position in the 2-pyrimidinone and 2-pyrazinone skeletons, a new group of compounds introduced with an aryl group or heteroaryl group having a substituent at the ortho position exhibits excellent control activity against plant diseases. The present inventors have found that the present invention has been completed.

That is, the present invention is as follows.

[式中、Ｒ１は、
水酸基、
シアノ基、
置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
Ｃ１～Ｃ６のハロアルキル基、
置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
Ｃ２～Ｃ６のハロアルケニル基、
置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
Ｃ２～Ｃ６のハロアルキニル基、
置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
Ｃ１～Ｃ６のハロアルコキシ基、
置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、
置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニルオキシ基、
Ｃ２～Ｃ６のハロアルケニルオキシ基、
置換基Ａで適宜置換されてもよいＣ３～Ｃ６のアルキニルオキシ基、
Ｃ３～Ｃ６のハロアルキニルオキシ基、
またはＲａＲｂＮ－（ここで、ＲａおよびＲｂは、それぞれ独立していて、水素原子、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、またはＣ３～Ｃ８のシクロアルキル基を表すか、あるいはＲａおよびＲｂは、結合する窒素原子と一緒になって、アジリジニル基、アゼチジニル基、ピロリジニル基、ピペリジニル基、ホモピペリジニル基、またはアゾカニル基を形成するものを表す。）を表し；
Ｒ２は、
シアノ基、
置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
Ｃ１～Ｃ６のハロアルキル基、
置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
Ｃ２～Ｃ６のハロアルケニル基、
置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
Ｃ２～Ｃ６のハロアルキニル基、
置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
Ｃ１～Ｃ６のハロアルコキシ基、
置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、
ＲａＲｂＮ－（ここで、ＲａおよびＲｂは前記と同義である。）、
Ｒｘ１Ｃ（＝Ｏ）－（ここで、Ｒｘ１は、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、またはＲａＲｂＮ－（ここで、ＲａおよびＲｂは前記と同義である。）を表す。）、
フェニル基、
５員～６員の複素環基、
または８～１０員の複素環基を表し、
該フェニル基は、Ｒ３が適宜０～５置換し（ただし、２置換以上のＲ３がある場合、Ｒ３はそれぞれ独立した置換基を表す。）、
該５～６員の複素環基、または該８～１０員の複素環基は、Ｒ３が適宜０～６置換し（ただし、２置換以上のＲ３がある場合、Ｒ３はそれぞれ独立した置換基を表す。）；
Ｒ３は、
水酸基、
シアノ基、
ニトロ基、
ハロゲン原子、
置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
Ｃ１～Ｃ６のハロアルキル基、
置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
Ｃ２～Ｃ６ハロアルケニル基、
置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
Ｃ２～Ｃ６のハロアルキニル基、
置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
Ｃ１～Ｃ６のハロアルコキシ基、
置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、
置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニルオキシ基、
Ｃ２～Ｃ６のハロアルケニルオキシ基、
置換基Ｃで適宜置換されてもよいＣ３～Ｃ６のアルキニルオキシ基、
Ｃ３～Ｃ６のハロアルキニルオキシ基、
置換基Ｄで適宜置換されてもよいアリール基、
置換基Ｄで適宜置換されてもよいヘテロアリール基、
置換基Ｄで適宜置換されてもよいアリールオキシ基、
置換基Ｄで適宜置換されてもよいヘテロアリールオキシ基、
置換基Ｄで適宜置換されてもよいアラルキルオキシ基、
ＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）、
Ｒｃ－Ｌ－（ここで、Ｒｃは、Ｃ１～Ｃ６のアルキル基、またはＣ１～Ｃ６のハロアルキル基を表し、Ｌは、Ｓ、ＳＯ、またはＳＯ_２を表す。）、
Ｒｘ１Ｃ（＝Ｏ）－（ここでＲｘ１は、前記と同義である。）、
Ｒｘ１Ｃ（＝Ｏ）Ｏ－（ここでＲｘ１は、前記と同義である。）、
Ｒｘ２Ｃ（＝Ｏ）Ｎ（Ｒｘ３）－（ここで、Ｒｘ２は、水素原子、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、またはＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）を表し、Ｒｘ３は、水素原子、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、またはＣ３～Ｃ８のシクロアルキル基を表す。）、
Ｒｘ４Ｒｘ５Ｃ＝Ｎ－Ｏ－（ここで、Ｒｘ４およびＲｘ５は、それぞれ独立していて、水素原子、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、またはＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）を表す。）、
または１～２個の酸素原子を含む３～６員環の基を表し；
Ｙは、
フェニル基、ピリジル基、ピリダジニル基、ピリミジニル基、ピラジニル基、トリアジニル基、テトラジニル基、チエニル基、チアゾリル基、イソチアゾリル基、またはチアジアゾリル基を表し、
該フェニル基は、Ｒ４がオルト位に置換し、さらにＲ５が適宜０～４置換し（ただし、２置換以上のＲ５がある場合、Ｒ５はそれぞれ独立した置換基を表す。）、
該ピリジル基、該ピリダジニル基、該ピリミジニル基、該ピラジニル基、該トリアジニル基、または該テトラジニル基は、Ｒ４がオルト位に置換し、さらにＲ５が適宜０～３置換し（ただし、２置換以上のＲ５がある場合、Ｒ５はそれぞれ独立した置換基を表す。）、
該チエニル基、該チアゾリル基、該イソチアゾリル基、または該チアジアゾリル基は、Ｒ４がオルト位に置換し、さらにＲ５が適宜０～２置換し（ただし、２置換以上のＲ５がある場合、Ｒ５はそれぞれ独立した置換基を表す。）、
Ｒ４は、
水酸基、
シアノ基、
ニトロ基、
ハロゲン原子、
置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
Ｃ１～Ｃ６のハロアルキル基、
置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
Ｃ２～Ｃ６ハロアルケニル基、
置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
Ｃ２～Ｃ６のハロアルキニル基、
置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
Ｃ１～Ｃ６のハロアルコキシ基、
置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、
置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニルオキシ基、
Ｃ２～Ｃ６のハロアルケニルオキシ基、
置換基Ｃで適宜置換されてもよいＣ３～Ｃ６のアルキニルオキシ基、
Ｃ３～Ｃ６のハロアルキニルオキシ基、
置換基Ｄで適宜置換されてもよいアリール基、
置換基Ｄで適宜置換されてもよいヘテロアリール基、
置換基Ｄで適宜置換されてもよいアラルキルオキシ基、
ＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）、
Ｒｃ－Ｌ－（ここで、ＲｃおよびＬは、前記と同義である。）、
Ｒｘ１Ｃ（＝Ｏ）－（ここでＲｘ１は、前記と同義である。）、
Ｒｘ１Ｃ（＝Ｏ）Ｏ－（ここでＲｘ１は、前記と同義である。）、
Ｒｘ２Ｃ（＝Ｏ）Ｎ（Ｒｘ３）－（ここで、Ｒｘ２は、水素原子、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、またはＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）を表し、Ｒｘ３は、水素原子、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、またはＣ３～Ｃ８のシクロアルキル基を表す。）、
Ｒｘ４Ｒｘ５Ｃ＝Ｎ－Ｏ－（ここで、Ｒｘ４およびＲｘ５は、それぞれ独立していて、水素原子、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、またはＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）を表す。）、
または１～２個の酸素原子を含む３～６員環の基を表し、
Ｒ５は、前記に記載のＲ４と同義であり；
Ｚ１は、Ｃ－Ｒ６、または窒素原子を表し、
Ｚ２は、Ｃ－Ｒ７、または窒素原子を表し、
該Ｚ１および該Ｚ２の少なくとも一方は窒素原子を表し；
Ｒ６は、
水素原子、
ハロゲン原子、
置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基
Ｃ１～Ｃ６のハロアルキル基、
置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
Ｃ２～Ｃ６のハロアルケニル基、
置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
Ｃ２～Ｃ６のハロアルキニル基、
置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
Ｃ１～Ｃ６のハロアルコキシ基、
またはＲｃ－Ｌ－（ここで、ＲｃおよびＬは、前記と同義である。）を表し；
Ｒ７は、
水素原子、
ハロゲン原子、
Ｃ１～Ｃ６のハロアルキル基、
置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
Ｃ２～Ｃ６のハロアルケニル基、
置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
Ｃ２～Ｃ６のハロアルキニル基、
置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
Ｃ１～Ｃ６のハロアルコキシ基、
Ｒｃ－Ｌ－（ここで、ＲｃおよびＬは、前記と同義である。）、
またはＲｘ１Ｃ（＝Ｏ）－（ここで、Ｒｘ１は、前記と同義である。）を表し；
Ｘは、酸素原子、または硫黄原子を表し；
そして、置換基Ａは、
水酸基、
シアノ基、
Ｃ３～Ｃ８のシクロアルキル基、
Ｃ１～Ｃ６のアルコキシ基、
Ｃ１～Ｃ６のハロアルコキシ基、
Ｃ３～Ｃ８のシクロアルコキシ基、
ＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）、
およびＲｃ－Ｌ－（ここで、ＲｃおよびＬは、前記と同義である。）からなる群から選択される少なくとも１種であり；
置換基Ｂは、
シアノ基、
Ｃ１～Ｃ６のアルコキシ基、
Ｃ１～Ｃ６のハロアルコキシ基、
およびＣ３～Ｃ８のシクロアルコキシ基からなる群から選択される少なくとも１種であり；
置換基Ｃは、
水酸基、
シアノ基、
Ｃ３～Ｃ８のシクロアルキル基、
Ｃ１～Ｃ６のアルコキシ基、
Ｃ１～Ｃ６のハロアルコキシ基、
Ｃ３～Ｃ８のシクロアルコキシ基、
Ｃ２～Ｃ６のアルコキシアルコキシ基、
ＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）、
Ｒｃ－Ｌ－（ここでＲｃおよびＬは、前記と同義である。）、
Ｒｘ１Ｃ（＝Ｏ）－（ここでＲｘ１は、前記と同義である。）、
Ｒｘ６Ｒｘ７Ｒｘ８Ｓｉ－（ここで、Ｒｘ６、Ｒｘ７およびＲｘ８は、それぞれ独立していてＣ１～Ｃ６のアルキル基を表す。）、
および１～２個の酸素原子を含む３～６員環の基からなる群から選択される少なくとも１種であり；
置換基Ｄは、
水酸基、
シアノ基、
ニトロ基、
ハロゲン原子、
置換基Ｂで置換されてもよいＣ１～Ｃ６のアルキル基、
Ｃ１～Ｃ６のハロアルキル基、
Ｃ３～Ｃ８のシクロアルキル基、
Ｃ１～Ｃ６のアルコキシ基、
Ｃ１～Ｃ６のハロアルコキシ基、
およびＣ３～Ｃ８のシクロアルコキシ基からなる群から選択される少なくとも１種である。］で表される含窒素複素環化合物またはその塩。[1]
formula (1)

[In the formula, R1 is
hydroxyl group,
cyano group,
a C1-C6 alkyl group optionally substituted with a substituent A,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with a substituent A,
a C2-C6 alkenyl group optionally substituted with a substituent A,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted with a substituent A,
a C2-C6 haloalkynyl group,
a C1-C6 alkoxy group optionally substituted with a substituent A,
a C1-C6 haloalkoxy group,
a C3-C8 cycloalkoxy group optionally substituted with a substituent A,
a C2-C6 alkenyloxy group optionally substituted with a substituent A,
a C2-C6 haloalkenyloxy group,
a C3-C6 alkynyloxy group optionally substituted with a substituent A,
a C3-C6 haloalkynyloxy group,
or RaRbN- (wherein Ra and Rb are each independently a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, or a C3-C8 Alternatively, Ra and Rb together with the attached nitrogen atom form an aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl, homopiperidinyl, or azocanyl group). represent;
R2 is
cyano group,
a C1-C6 alkyl group optionally substituted with a substituent A,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with a substituent A,
a C2-C6 alkenyl group optionally substituted with a substituent A,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted with a substituent A,
a C2-C6 haloalkynyl group,
a C1-C6 alkoxy group optionally substituted with a substituent A,
a C1-C6 haloalkoxy group,
a C3-C8 cycloalkoxy group optionally substituted with a substituent A,
RaRbN- (where Ra and Rb are as defined above),
Rx1C(=O)-(wherein Rx1 is a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or RaRbN- (wherein Ra and Rb are as defined above.),
phenyl group,
a 5- to 6-membered heterocyclic group,
or represents an 8- to 10-membered heterocyclic group,
the phenyl group is optionally substituted with 0 to 5 R3 (provided that when there are two or more substituted R3, each R3 represents an independent substituent);
The 5- to 6-membered heterocyclic group or the 8- to 10-membered heterocyclic group is optionally substituted with 0 to 6 R3 (provided that when there are 2 or more R3s, each R3 is an independent substituent. show.);
R3 is
hydroxyl group,
cyano group,
nitro group,
halogen atom,
a C1 to C6 alkyl group optionally substituted with a substituent C,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with a substituent C,
a C2-C6 alkenyl group optionally substituted with a substituent C,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted with a substituent C,
a C2-C6 haloalkynyl group,
a C1-C6 alkoxy group optionally substituted with a substituent C,
a C1-C6 haloalkoxy group,
a C3-C8 cycloalkoxy group optionally substituted with a substituent C,
a C2-C6 alkenyloxy group optionally substituted with a substituent C,
a C2-C6 haloalkenyloxy group,
a C3-C6 alkynyloxy group optionally substituted with a substituent C,
a C3-C6 haloalkynyloxy group,
an aryl group optionally substituted with a substituent D,
a heteroaryl group optionally substituted with a substituent D,
an aryloxy group optionally substituted with a substituent D,
a heteroaryloxy group optionally substituted with a substituent D,
an aralkyloxy group optionally substituted with a substituent D,
RaRbN- (wherein Ra and Rb are as defined above),
Rc-L- (wherein Rc represents a C1-C6 alkyl group or a C1 _- C6 haloalkyl group, and L represents S, SO, or SO2),
Rx1C (=O) - (where Rx1 is as defined above),
Rx1C(=O)O- (wherein Rx1 has the same definition as above),
Rx2C(=O)N(Rx3)- (here, Rx2 is a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or RaRbN- (wherein Ra and Rb are as defined above), and Rx3 is represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group),
Rx4Rx5C=NO- (here, Rx4 and Rx5 are each independently a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3- represents a C8 cycloalkyl group, a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group, or RaRbN- (wherein Ra and Rb are as defined above); ),
or represents a 3- to 6-membered ring group containing 1 to 2 oxygen atoms;
Y is
a phenyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, a tetrazinyl group, a thienyl group, a thiazolyl group, an isothiazolyl group, or a thiadiazolyl group;
the phenyl group is substituted with R4 at the ortho position and further optionally substituted with 0 to 4 R5 (provided that when there are two or more substituted R5, each R5 represents an independent substituent);
The pyridyl group, the pyridazinyl group, the pyrimidinyl group, the pyrazinyl group, the triazinyl group, or the tetrazinyl group is substituted with R4 at the ortho position, and optionally with 0 to 3 substituents with R5 (provided that 2 or more substituents are substituted). When R5 is present, each R5 represents an independent substituent.),
In the thienyl group, the thiazolyl group, the isothiazolyl group, or the thiadiazolyl group, R4 is substituted at the ortho position, and R5 is optionally substituted with 0 to 2 (provided that when there are two or more substituted R5, each R5 is represents an independent substituent.),
R4 is
hydroxyl group,
cyano group,
nitro group,
halogen atom,
a C1 to C6 alkyl group optionally substituted with a substituent C,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with a substituent C,
a C2-C6 alkenyl group optionally substituted with a substituent C,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted with a substituent C,
a C2-C6 haloalkynyl group,
a C1-C6 alkoxy group optionally substituted with a substituent C,
a C1-C6 haloalkoxy group,
a C3-C8 cycloalkoxy group optionally substituted with a substituent C,
a C2-C6 alkenyloxy group optionally substituted with a substituent C,
a C2-C6 haloalkenyloxy group,
a C3-C6 alkynyloxy group optionally substituted with a substituent C,
a C3-C6 haloalkynyloxy group,
an aryl group optionally substituted with a substituent D,
a heteroaryl group optionally substituted with a substituent D,
an aralkyloxy group optionally substituted with a substituent D,
RaRbN- (wherein Ra and Rb are as defined above),
Rc-L- (wherein Rc and L are as defined above),
Rx1C (=O) - (where Rx1 is as defined above),
Rx1C(=O)O- (wherein Rx1 has the same definition as above),
Rx2C(=O)N(Rx3)- (here, Rx2 is a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or RaRbN- (wherein Ra and Rb are as defined above), and Rx3 is represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group),
Rx4Rx5C=NO- (here, Rx4 and Rx5 are each independently a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3- represents a C8 cycloalkyl group, a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group, or RaRbN- (wherein Ra and Rb are as defined above); ),
or represents a 3- to 6-membered ring group containing 1 to 2 oxygen atoms,
R5 has the same definition as R4 described above;
Z1 represents C—R6 or a nitrogen atom;
Z2 represents C—R7 or a nitrogen atom;
at least one of said Z1 and said Z2 represents a nitrogen atom;
R6 is
hydrogen atom,
halogen atom,
a C1-C6 alkyl group C1-C6 haloalkyl group optionally substituted with a substituent A;
a C3-C8 cycloalkyl group optionally substituted with a substituent A,
a C2-C6 alkenyl group optionally substituted with a substituent A,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted with a substituent A,
a C2-C6 haloalkynyl group,
a C1-C6 alkoxy group optionally substituted with a substituent A,
a C1-C6 haloalkoxy group,
or Rc-L- (wherein Rc and L are as defined above);
R7 is
hydrogen atom,
halogen atom,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with a substituent A,
a C2-C6 alkenyl group optionally substituted with a substituent A,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted with a substituent A,
a C2-C6 haloalkynyl group,
a C1-C6 alkoxy group optionally substituted with a substituent A,
a C1-C6 haloalkoxy group,
Rc-L- (wherein Rc and L are as defined above),
or Rx1C (=O) - (wherein Rx1 is as defined above);
X represents an oxygen atom or a sulfur atom;
And the substituent A is
hydroxyl group,
cyano group,
a C3-C8 cycloalkyl group,
a C1-C6 alkoxy group,
a C1-C6 haloalkoxy group,
a C3-C8 cycloalkoxy group,
RaRbN- (wherein Ra and Rb are as defined above),
and Rc-L- (wherein Rc and L are as defined above); at least one selected from the group;
Substituent B is
cyano group,
a C1-C6 alkoxy group,
a C1-C6 haloalkoxy group,
and at least one selected from the group consisting of C3-C8 cycloalkoxy groups;
Substituent C is
hydroxyl group,
cyano group,
a C3-C8 cycloalkyl group,
a C1-C6 alkoxy group,
a C1-C6 haloalkoxy group,
a C3-C8 cycloalkoxy group,
a C2-C6 alkoxyalkoxy group,
RaRbN- (wherein Ra and Rb are as defined above),
Rc-L- (wherein Rc and L are as defined above),
Rx1C (=O) - (where Rx1 is as defined above),
Rx6Rx7Rx8Si- (wherein Rx6, Rx7 and Rx8 each independently represent a C1-C6 alkyl group),
and at least one selected from the group consisting of a 3- to 6-membered ring group containing 1 to 2 oxygen atoms;
Substituent D is
hydroxyl group,
cyano group,
nitro group,
halogen atom,
a C1-C6 alkyl group optionally substituted by a substituent B,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group,
a C1-C6 alkoxy group,
a C1-C6 haloalkoxy group,
and at least one selected from the group consisting of C3-C8 cycloalkoxy groups. ] A nitrogen-containing heterocyclic compound or a salt thereof.

[2]
R2 is
cyano group,
a C1-C6 alkyl group optionally substituted with a substituent A,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with a substituent A,
a C2-C6 alkenyl group optionally substituted with a substituent A,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted with a substituent A,
a C2-C6 haloalkynyl group,
a C1-C6 alkoxy group optionally substituted with a substituent A,
a C1-C6 haloalkoxy group,
a C3-C8 cycloalkoxy group optionally substituted with a substituent A,
RaRbN- (wherein Ra and Rb are each independently a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, or a C3-C8 cyclo an alkyl group, or Ra and Rb together with the attached nitrogen atom form an aziridinyl group, azetidinyl group, pyrrolidinyl group, piperidinyl group, homopiperidinyl group, or azocanyl group),
Rx1C(=O)-(wherein Rx1 is a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or RaRbN- (wherein Ra and Rb are as defined above),
phenyl group, pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, tetrazinyl group, thienyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, thiatriazolyl group, pyrrolyl group, pyrazolyl group, imidazolyl group, triazolyl group, tetrazolyl group , pentazolyl group, furyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, indolyl group, isoindolyl group, indazolyl group, benzimidazolyl group, benzotriazolyl group, benzofuryl group, isobenzofuryl group, benzoxazolyl group, benzothienyl group, benzothiazolyl group, benzoisothiazolyl group, benzothiadiazolyl group, indolizinyl group, imidazopyridyl group, pyrazolopyridyl group, triazolopyridyl group, pyrrolopyrimidinyl group, imidazopyrimidinyl group, pyrazolopyrimidinyl group, triazolopyrimidinyl group a pyrrolopyrazinyl group, an imidazopyrazinyl group, a pyrazolopyrazinyl group, a triazolopyrazinyl group, a quinolyl group, an isoquinolyl group, a cinolyl group, a phthalazinyl group, a quinoxalinyl group, a quinazolinyl group, or a napthyridinyl group;
the phenyl group is optionally substituted with 0 to 5 R3 (provided that when there are two or more substituted R3, each R3 represents an independent substituent);
The pyridyl group, the pyridazinyl group, the pyrimidinyl group, the pyrazinyl group, the triazinyl group, or the tetrazinyl group is optionally substituted with 0 to 4 R3s (provided that when there are two or more R3s, each R3 is independently represents a substituent that has
The thienyl group, the thiazolyl group, the isothiazolyl group, the thiadiazolyl group, or the thiatriazolyl group is optionally substituted by 0 to 3 R3 (provided that when there are two or more substituted R3, each R3 is an independent substituent. show.),
The pyrrolyl group, the pyrazolyl group, the imidazolyl group, the triazolyl group, the tetrazolyl group, or the pentazolyl group is optionally substituted with 0 to 4 R3 (provided that when there are two or more R3 substituted, each R3 is independently represents a substituent that has
the furyl group, the oxazolyl group, the isoxazolyl group, or the oxadiazolyl group is optionally substituted with 0 to 3 R3 (provided that when there are two or more substituted R3, each R3 represents an independent substituent);
The indolyl group, the isoindolyl group, the indazolyl group, the benzimidazolyl group, or the benzotriazolyl group is optionally substituted with 0 to 6 R3s (provided that when there are two or more R3s, each R3 is independently represents a substituent.),
The benzofuryl group, the isobenzofuryl group, or the benzoxazolyl group is optionally substituted with 0 to 5 R3 (provided that when there are two or more R3 substituted, each R3 represents an independent substituent). ,
The benzothienyl group, the benzothiazolyl group, the benzoisothiazolyl group, or the benzothiadiazolyl group is optionally substituted with 0 to 5 R3 (provided that when there are two or more substituted R3, each R3 is independently represents a substituent.),
The indolizinyl group, the imidazopyridyl group, the pyrazolopyridyl group, or the triazolopyridyl group is optionally substituted with 0 to 6 R3s (provided that when there are two or more R3s, each R3 is an independent substituent represents ),
The pyrrolopyrimidinyl group, the imidazopyrimidinyl group, the pyrazolopyrimidinyl group, the triazolopyrimidinyl group, the pyrrolopyrazinyl group, the imidazopyrazinyl group, the pyrazolopyrazinyl group, or the triazolopyrazinyl group , where R3 is optionally substituted with 0 to 5 substituents (provided that when there are two or more substituted R3, each R3 represents an independent substituent);
The quinolyl group, the isoquinolyl group, the cinolyl group, the phthalazinyl group, the quinoxalinyl group, the quinazolinyl group, or the naphthyridinyl group is optionally substituted with 0 to 6 R3 (provided that when there are 2 or more R3 substitutions, Each R3 represents an independent substituent.),
The nitrogen-containing heterocyclic compound according to [1] above, or a salt thereof.

[3]
R1 is
cyano group,
a C1-C6 alkyl group optionally substituted with a substituent A,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with a substituent A,
a C2-C6 alkenyl group optionally substituted with a substituent A,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted with a substituent A,
or represents a C2-C6 haloalkynyl group;
R2 is
a C1-C6 alkyl group optionally substituted with a substituent A,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with a substituent A,
a C1-C6 alkoxy group optionally substituted with a substituent A,
a C1-C6 haloalkoxy group,
a C3-C8 cycloalkoxy group optionally substituted with a substituent A,
RaRbN- (wherein Ra and Rb are each independently a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, or a C3-C8 cyclo an alkyl group, or Ra and Rb together with the attached nitrogen atom form an aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl, homopiperidinyl, or azocanyl group),
Rx1C(=O)-(wherein Rx1 is a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or RaRbN- (wherein Ra and Rb are as defined above.),
phenyl group, pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, tetrazinyl group, thienyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, thiatriazolyl group, pyrrolyl group, pyrazolyl group, imidazolyl group, triazolyl group, tetrazolyl group , a pentazolyl group, a furyl group, an oxazolyl group, an isoxazolyl group, or an oxadiazolyl group,
the phenyl group is optionally substituted with 0 to 5 R3 (provided that when there are two or more substituted R3, each R3 represents an independent substituent);
The pyridyl group, the pyridazinyl group, the pyrimidinyl group, the pyrazinyl group, the triazinyl group, or the tetrazinyl group is optionally substituted with 0 to 4 R3 (provided that when there are two or more substituted R3, each R3 is independently represents a substituent that has
The thienyl group, the thiazolyl group, the isothiazolyl group, the thiadiazolyl group, or the thiatriazolyl group is optionally substituted with 0 to 3 R3 (provided that when there are two or more R3 substituted, each R3 is an independent substituent. show.),
The pyrrolyl group, the pyrazolyl group, the imidazolyl group, the triazolyl group, the tetrazolyl group, or the pentazolyl group is appropriately substituted with 0 to 4 R3 (provided that when there are two or more R3 substituted, each R3 is independently represents a substituent that has
the furyl group, the oxazolyl group, the isoxazolyl group, or the oxadiazolyl group, optionally substituted with 0 to 3 R3 (provided that when there are two or more R3 substituted, each R3 represents an independent substituent);
R3 is
hydroxyl group,
cyano group,
halogen atom,
a C1 to C6 alkyl group optionally substituted with a substituent C,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with a substituent C,
a C2-C6 alkenyl group optionally substituted with a substituent C,
a C2-C6 alkynyl group optionally substituted with a substituent C,
a C1-C6 alkoxy group optionally substituted with a substituent C,
a C1-C6 haloalkoxy group,
a C3-C8 cycloalkoxy group optionally substituted with a substituent C,
a C2-C6 alkenyloxy group optionally substituted with a substituent C,
a C2-C6 haloalkenyloxy group,
a C3-C6 alkynyloxy group optionally substituted with a substituent C,
or represents a C3-C6 haloalkynyloxy group;
Y is
phenyl group,
or represents a pyridyl group,
the phenyl group is substituted with R4 at the ortho position and further optionally substituted with 0 to 4 R5 (provided that when there are two or more substituted R5, each R5 represents an independent substituent);
The pyridyl group is substituted with R4 at the ortho position and optionally substituted with 0 to 3 R5 (provided that when there are two or more substituted R5, each R5 represents an independent substituent),
R4 is
halogen atom,
a C1 to C6 alkyl group optionally substituted with a substituent C,
a C1-C6 haloalkyl group,
a C1-C6 alkoxy group optionally substituted with a substituent C,
or represents a C1-C6 haloalkoxy group,
R5 is
hydroxyl group,
cyano group,
halogen atom,
a C1 to C6 alkyl group optionally substituted with a substituent C,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with a substituent C,
a C2-C6 alkenyl group optionally substituted with a substituent C,
a C2-C6 alkynyl group optionally substituted with a substituent C,
a C1-C6 alkoxy group optionally substituted with a substituent C,
a C1-C6 haloalkoxy group,
a C3-C8 cycloalkoxy group optionally substituted with a substituent C,
a C2-C6 alkenyloxy group optionally substituted with a substituent C,
a C3-C6 alkynyloxy group optionally substituted with a substituent C,
a heteroaryl group optionally substituted with a substituent D,
Rc-L- (wherein Rc represents a C1-C6 alkyl group or a C1 _- C6 haloalkyl group, and L represents S, SO, or SO2),
or Rx1C (=O) O- (where Rx1 is as defined above),
R6 is
hydrogen atom,
halogen atom,
a C1-C6 alkyl group optionally substituted with a substituent A,
a C3-C8 cycloalkyl group optionally substituted with a C1-C6 haloalkyl group substituent A,
a C1-C6 alkoxy group optionally substituted with a substituent A,
or represents a C1-C6 haloalkoxy group,
R7 is
hydrogen atom,
halogen atom,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with a substituent A,
a C1-C6 alkoxy group optionally substituted with a substituent A,
or represents a C1-C6 haloalkoxy group,
The nitrogen-containing heterocyclic compound or a salt thereof according to [2] above.

[4]
R1 is
a C1-C6 alkyl group optionally substituted with a substituent A,
or represents a C1-C6 haloalkyl group;
R2 is
a C1-C6 alkyl group optionally substituted with a substituent A,
a C1-C6 haloalkyl group,
Rx1C(=O)-(wherein Rx1 is a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or RaRbN- (wherein Ra and Rb are as defined above.),
or represents a phenyl group,
the phenyl group is optionally substituted with 0 to 5 R3 (provided that when there are two or more substituted R3, each R3 represents an independent substituent);
R3 is
halogen atom,
a C1 to C6 alkyl group optionally substituted with a substituent C,
or represents a C1-C6 alkoxy group optionally substituted with a substituent C;
Y is
represents a phenyl group,
the phenyl group is substituted with R4 at the ortho position and further optionally substituted with 0 to 4 R5 (provided that when there are two or more substituted R5, each R5 represents an independent substituent);
R4 is
halogen atom,
a C1 to C6 alkyl group optionally substituted with a substituent C,
or represents a C1-C6 alkoxy group optionally substituted with a substituent C,
R5 is
cyano group,
halogen atom,
a C1-C6 alkoxy group optionally substituted with a substituent C,
or represents a C1-C6 haloalkoxy group;
R6 is
hydrogen atom,
halogen atom,
a C1-C6 alkyl group optionally substituted with a substituent A,
or represents a C1-C6 haloalkyl group,
R7 is
hydrogen atom,
Or the compound or its salt according to the above [3], which represents a halogen atom.

の部分構造を表す、［１］～［１３］のいずれか１つに記載の化合物またはその塩。
［１５］
Ｙは、
式（ｋ－１）、または式（ｋ－４）

の部分構造を表す、［１］～［１３］のいずれか１つに記載の化合物またはその塩。
［１６］
Ｒ４は、
ハロゲン原子を表す、［１］～［１５］のいずれか１つに記載の化合物またはその塩。
［１７］
Ｒ４は、
フッ素原子、塩素原子、臭素原子、ヨウ素原子、メチル基、エチル基、メトキシ基、エトキシ基、プロピルオキシ基、またはイソプロピルオキシ基を表す、［１］～［１５］のいずれか１つに記載の化合物またはその塩。
［１８］
Ｒ４は、
フッ素原子を表す、［１］～［１５］のいずれか１つに記載の化合物またはその塩。
［１９］
Ｒ５は、
ハロゲン原子、置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、またはＣ１～Ｃ６のハロアルコキシ基を表す、［１］～［１８］のいずれか１つに記載の化合物またはその塩。
［２０］
Ｒ５は、
シアノ基、フッ素原子、塩素原子、臭素原子、ヨウ素原子、メトキシ基、エトキシ基、プロピルオキシ基、イソプロピルオキシ基、ジフルオロメトキシ基、トリフルオロメトキシ基、２，２－ジフルオロエトキシ基、または２，２，２－トリフルオロエトキシ基を表す、［１］～［１８］のいずれか１つに記載の化合物またはその塩。
［２１］
Ｒ５は、
フッ素原子、メトキシ基、または２，２，２－トリフルオロエトキシ基を表す、［１］～［１８］のいずれか１つに記載の化合物またはその塩。
［２２］
Ｚ１は、Ｃ－Ｒ６を表し、 Ｚ２は、窒素原子を表す、［１］～［２１］のいずれか１つに記載の化合物またはその塩。
［２３］
Ｚ１は、窒素原子を表し、 Ｚ２は、Ｃ－Ｒ７を表す、［１］～［２１］のいずれか１つに記載の化合物またはその塩。
［２４］
Ｚ１は、窒素原子を表し、 Ｚ２は、窒素原子を表す、［１］～［２１］のいずれか１つに記載の化合物またはその塩。
［２５］
Ｒ６は、
水素原子、またはハロゲン原子を表す［１］～［２２］のいずれか１つに記載の化合物またはその塩。
［２６］
Ｒ６は、
水素原子、フッ素原子、塩素原子、臭素原子、ヨウ素原子、メチル基、エチル基、プロピル基、ジフルオロメチル基、トリフルオロメチル基、２－フルオロエチル基、２，２－ジフルオロエチル基、または２，２，２－トリフルオロエチル基を表す［１］～［２２］のいずれか１つに記載の化合物またはその塩。
［２７］
Ｒ６は、
水素原子、または塩素原子を表す［１］～［２２］のいずれか１つに記載の化合物またはその塩。
［２８］
Ｒ７は、
水素原子、フッ素原子、塩素原子、臭素原子、またはヨウ素原子を表す［１］～［２１］、および［２３］のいずれか１つに記載の化合物またはその塩。
［２９］
Ｒ７は、
水素原子を表す［１］～［２１］、および［２３］のいずれか１つに記載の化合物またはその塩。
［３０］
Ｘは、
酸素原子を表す［１］～［２９］のいずれか１つに記載の化合物またはその塩。
［３１］
Ｘは、
硫黄原子を表す［１］～［２９］のいずれか１つに記載の化合物またはその塩。
［３２］
［１］～［３１］に記載の化合物またはその塩を有効成分として含有する農園芸用有害生物防除剤。
［３３］
［１］～［３１］に記載の化合物またはその塩を有効成分として含有する農園芸用殺菌剤。
［３４］
［３２］に記載の農園芸用有害生物防除剤を、植物、植物の種子、または植物を栽培する土壌に施用することを含む、植物病害を防除する方法。
［３５］
［３３］に記載の農園芸用殺菌剤を、植物、植物の種子、または植物を栽培する土壌に施用することを含む、植物病害を防除する方法。
［３６］
農園芸用有害生物防除剤としての［１］～［３１］のいずれか１つに記載の化合物の使用。
［３７］
農園芸用殺菌剤としての［１］～［３１］のいずれか１つに記載の化合物の使用。[5]
R1 is
The compound or a salt thereof according to any one of [1] to [4], which represents a C1 to C6 alkyl group or a C1 to C6 haloalkyl group.
[6]
R1 is
any one of [1] to [4], which is a methyl group, ethyl group, propyl group, isobutyl group, 2-fluoroethyl group, 2,2-difluoroethyl group, or 2,2,2-trifluoroethyl group A compound according to one, or a salt thereof.
[7]
R1 is
The compound according to any one of [1] to [4], which is a methyl group, ethyl group, isobutyl group, or 2,2-difluoroethyl group, or a salt thereof.
[8]
R2 is
A C1-C6 alkyl group optionally substituted with a substituent A, Rx1C(=O)-(wherein Rx1 is a C1-C6 alkyl group optionally substituted with a substituent B, C1-C6 a haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or RaRbN— (wherein Ra and Rb are as defined above ), or a phenyl group (the phenyl group is optionally substituted with 0 to 5 R3 (provided that when there are two or more R3s, each R3 represents an independent substituent))) The compound according to any one of [1] to [7], or a salt thereof.
[9]
R2 is
methyl group, ethyl group, isopropyl group, isobutyl group, difluoromethyl group, trifluoromethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, acetyl group, methoxyacetyl group, cyanoacetyl group , difluoroacetyl group, trifluoroacetyl group, methoxycarbonyl group, ethoxycarbonyl group, phenyl group, 2-fluorophenyl group, 2-chlorophenyl group, 2-bromophenyl group, 2-iodophenyl group, 2-methoxyphenyl group, 3-fluorophenyl group, 3-chlorophenyl group, 3-bromophenyl group, 3-iodophenyl group, 3-methoxyphenyl group, 4-chlorophenyl group, 4-bromophenyl group, 4-iodophenyl group, 4-methoxyphenyl group, 2,3-difluorophenyl group, 2,4-difluorophenyl group, 2,5-difluorophenyl group, 2,6-difluorophenyl group, 2-chloro-3-fluorophenyl group, 2-chloro-4- fluorophenyl group, 2-chloro-5-fluorophenyl group, 2-chloro-6-fluorophenyl group, 2-bromo-3-fluorophenyl group, 2-bromo-4-fluorophenyl group, 2-bromo-5- fluorophenyl group, 2-bromo-6-fluorophenyl group, 2-fluoro-3-methoxyphenyl group, 2-fluoro-4-methoxyphenyl group, 2-fluoro-5-methoxyphenyl group, 2-fluoro-6- methoxyphenyl group, 2-chloro-3-methoxyphenyl group, 2-chloro-4-methoxyphenyl group, 2-chloro-5-methoxyphenyl group, 2-chloro-6-methoxyphenyl group, 2-bromo-3- methoxyphenyl group, 2-bromo-4-methoxyphenyl group, 2-bromo-5-methoxyphenyl group, 2-bromo-6-methoxyphenyl group, 2,3,4-trifluorophenyl group, 2,3,5 -trifluorophenyl group, 2,3,6-trifluorophenyl group, 2-chloro-3,4-difluorophenyl group, 2-chloro-3,5-difluorophenyl group, 2-chloro-3,6-difluoro phenyl group, 2-bromo-3,4-difluorophenyl group, 2-bromo-3,5-difluorophenyl group, 2-bromo-3,6-difluorophenyl group, 2-fluoro-3,4-dimethoxyphenyl group, 2-fluoro-3,5-dimethoxyphenyl group, 2-fluoro-3,6-dimethoxyphenyl group, 2-chloro-3,4-dimethoxyphenyl group Nyl group, 2-chloro-3,5-dimethoxyphenyl group, 2-chloro-3,6-dimethoxyphenyl group, 2-bromo-3,4-dimethoxyphenyl group, 2-bromo-3,5-dimethoxyphenyl group , or a compound according to any one of [1] to [7], which represents a 2-bromo-3,6-dimethoxyphenyl group, or a salt thereof.
[10]
R2 is
represents a methyl group, isopropyl group, ethoxycarbonyl group, 2-fluorophenyl group, 2-chlorophenyl group, 2-chloro-5-methoxyphenyl group, or 2-chloro-3,5-difluorophenyl group, [1] to The compound according to any one of [7], or a salt thereof.
[11]
R3 is
The compound or a salt thereof according to any one of [1] to [8], which represents a halogen atom or a C1 to C6 alkoxy group optionally substituted with a substituent C;
[12]
R3 is
fluorine atom, chlorine atom, bromine atom, iodine atom, methyl group, ethyl group, propyl group, isopropyl group, methoxy group, ethoxy group, propyloxy group, or isopropyloxy group, any of [1] to [8] or a salt thereof.
[13]
R3 is
The compound or salt thereof according to any one of [1] to [8], which represents a fluorine atom, a chlorine atom, or a methoxy group.
[14]
Y is
Formula (k-1), Formula (k-2), Formula (k-3), Formula (k-4), Formula (k-5), Formula (k-6)

The compound or salt thereof according to any one of [1] to [13], which represents a partial structure of
[15]
Y is
Formula (k-1) or Formula (k-4)

The compound or salt thereof according to any one of [1] to [13], which represents a partial structure of
[16]
R4 is
The compound or salt thereof according to any one of [1] to [15], which represents a halogen atom.
[17]
R4 is
Any one of [1] to [15], which represents a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a methyl group, an ethyl group, a methoxy group, an ethoxy group, a propyloxy group, or an isopropyloxy group. compound or its salt.
[18]
R4 is
The compound or salt thereof according to any one of [1] to [15], which represents a fluorine atom.
[19]
R5 is
The compound or salt thereof according to any one of [1] to [18], which represents a halogen atom, a C1 to C6 alkoxy group optionally substituted with a substituent C, or a C1 to C6 haloalkoxy group, or a salt thereof .
[20]
R5 is
cyano group, fluorine atom, chlorine atom, bromine atom, iodine atom, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, difluoromethoxy group, trifluoromethoxy group, 2,2-difluoroethoxy group, or 2,2 ,2-trifluoroethoxy group, the compound or a salt thereof according to any one of [1] to [18].
[21]
R5 is
The compound or salt thereof according to any one of [1] to [18], which represents a fluorine atom, a methoxy group, or a 2,2,2-trifluoroethoxy group.
[22]
The compound or salt thereof according to any one of [1] to [21], wherein Z1 represents C—R6, and Z2 represents a nitrogen atom.
[23]
The compound or salt thereof according to any one of [1] to [21], wherein Z1 represents a nitrogen atom and Z2 represents C—R7.
[24]
The compound or salt thereof according to any one of [1] to [21], wherein Z1 represents a nitrogen atom and Z2 represents a nitrogen atom.
[25]
R6 is
The compound or salt thereof according to any one of [1] to [22], which represents a hydrogen atom or a halogen atom.
[26]
R6 is
hydrogen atom, fluorine atom, chlorine atom, bromine atom, iodine atom, methyl group, ethyl group, propyl group, difluoromethyl group, trifluoromethyl group, 2-fluoroethyl group, 2,2-difluoroethyl group, or 2, The compound or a salt thereof according to any one of [1] to [22], which represents a 2,2-trifluoroethyl group.
[27]
R6 is
The compound or salt thereof according to any one of [1] to [22], which represents a hydrogen atom or a chlorine atom.
[28]
R7 is
The compound or salt thereof according to any one of [1] to [21] and [23], which represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.
[29]
R7 is
The compound or salt thereof according to any one of [1] to [21] and [23], which represents a hydrogen atom.
[30]
X is
The compound or salt thereof according to any one of [1] to [29], which represents an oxygen atom.
[31]
X is
The compound or salt thereof according to any one of [1] to [29], which represents a sulfur atom.
[32]
An agricultural and horticultural pest control agent containing the compound or its salt according to [1] to [31] as an active ingredient.
[33]
An agricultural and horticultural fungicide containing the compound or a salt thereof according to [1] to [31] as an active ingredient.
[34]
A method for controlling plant diseases, which comprises applying the agricultural and horticultural pest control agent according to [32] to plants, plant seeds, or soil for cultivating plants.
[35]
A method for controlling plant diseases, which comprises applying the agricultural and horticultural fungicide of [33] to plants, plant seeds, or soil for cultivating plants.
[36]
Use of the compound according to any one of [1] to [31] as an agricultural and horticultural pest control agent.
[37]
Use of the compound according to any one of [1] to [31] as an agricultural and horticultural fungicide.

INDUSTRIAL APPLICABILITY According to the present invention, it is possible to provide a novel compound that is effective as an agricultural and horticultural pest control agent, particularly as an agricultural and horticultural fungicide.

DETAILED DESCRIPTION OF THE INVENTION Embodiments for carrying out the present invention will be described in detail below.

Unless otherwise specified, each term used in the claims and the specification shall be defined as generally used in the technical field.

The abbreviations used in this specification are described below.

DMF: N,N-dimethylformamide, THF: tetrahydrofuran, Me: methyl group, Et: ethyl group, Pr: propyl group, Bu: butyl group, Ac: acetyl group, Ph: phenyl group, Py: pyridyl group, c: cyclo, i: iso, sec: secondary, t: tertiary, =: double bond, ≡: triple bond. Pr and Bu in the columns of the table mean normal if there is no prefix.

Definitions of terms used in this specification are described below.

The description Cx-Cy represents having x to y carbon atoms. It is understood that x and y represent integers and that all integers between x and y are also individually disclosed. For example, C1-C6 are 1, 2, 3, 4, 5, or 6 carbon atoms, C2-C6 are 2, 3, 4, 5, or 6 carbon atoms, C3-C8 are , 3, 4, 5, 6, 7, or 8 carbon atoms, C3-C6 are 3, 4, 5, or 6 carbon atoms, C1-C5 are 1, 2, 3, 4 , or 5 carbon atoms, and C1-C3 means having 1, 2, or 3 carbon atoms, respectively.

The term "optionally substituted" means substituted or unsubstituted. In using this term, if the number of substituents is not specified, it means that the number of substituents is one. On the other hand, for example, when the number of substituents is specified as "optionally substituted with 0 to 6", it is understood that all integers between 0 and 6 are also individually disclosed. be done. That is, it means that there are none, 1, 2, 3, 4, 5, or 6 substituents. Similarly, in "optionally substituted with 0 to 5 substituents", the number of substituents is none, 1, 2, 3, 4, or 5. In "optionally substituted with 0 to 4 substituents" , the number of substituents is none, 1, 2, 3, or 4, and "optionally substituted with 0 to 3" means that none, 1, 2, or 3 substituents are "optionally "optionally substituted with 0 to 2" means having none, 1, or 2 substituents, respectively.

The C1-C6 alkyl group may be linear or branched, and is methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, t-butyl group, pentyl group, isopentyl group, 2-methylbutyl group, neopentyl group, 1-ethylpropyl group, hexyl group, 4-methylpentyl group, 3-methylpentyl group, 2-methylpentyl group, 1-methylpentyl group, 3,3-dimethylbutyl group , 2,2-dimethylbutyl group, 1,1-dimethylbutyl group, 1,2-dimethylbutyl group, 1,3-dimethylbutyl group, 2,3-dimethylbutyl group, 2-ethylbutyl group, 1-isopropylpropyl group, 1,1,2-trimethylpropyl group, 1,2,2-trimethylpropyl group and the like.

A halogen atom includes a fluorine atom, a chlorine atom, a bromine atom, an iodine atom and the like.

The C1-C6 haloalkyl group represents a C1-C6 alkyl group in which hydrogen atoms in the above-mentioned C1-C6 alkyl groups are optionally substituted with one or more halogen atoms. When substituted with two or more halogen atoms, those halogen atoms may be the same or different, and the number of substitutions is not particularly limited as long as they can exist as substituents.

Specific examples of C1 to C6 haloalkyl groups include monofluoromethyl group, difluoromethyl group, trifluoromethyl group, monochloromethyl group, monobromomethyl group, monoiodomethyl group, chlorodifluoromethyl group, bromodifluoromethyl group, 1 -fluoroethyl group, 2-fluoroethyl group, 1,1-difluoroethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, 1,1,2,2-tetrafluoroethyl group , pentafluoroethyl group, 2,2,2-trichloroethyl group, 3,3-difluoropropyl group, 3,3,3-trifluoropropyl group, heptafluoropropyl group, heptafluoroisopropyl group, 2,2,2 -trifluoro-1-(trifluoromethyl)ethyl group, nonafluorobutyl group, nonafluoro-sec-butyl group, 3,3,4,4,5,5,5-heptafluoropentyl group, undecafluoropentyl group , tridecafluorohexyl group, and the like.

The C3-C8 cycloalkyl group includes a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group and the like.

The C2-C6 alkenyl group means a linear or branched unsaturated hydrocarbon group having one or more double bonds. In addition, when there is a geometric isomer, it is either E-isomer or Z-isomer only, or a mixture of E-isomer and Z-isomer in any ratio, and if it is within the specified carbon number range, it is not particularly limited. never

Specific examples of C2-C6 alkenyl groups include vinyl, 1-propenyl, allyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl and 3-pentenyl. group, 4-pentenyl group, 3-methyl-2-butenyl group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group, 4-methyl-3-pentenyl group, 3-methyl-2-pentenyl group and the like.

The C2-C6 haloalkenyl group represents a C2-C6 alkenyl group in which the hydrogen atoms in the above C2-C6 alkenyl group are optionally substituted with one or more halogen atoms. When substituted with two or more halogen atoms, those halogen atoms may be the same or different, and the number of substitutions is not particularly limited as long as they can exist as substituents.

Specific examples of C2 to C6 haloalkenyl groups include 2-fluorovinyl group, 2,2-difluorovinyl group, 2,2-dichlorovinyl group, 3-fluoroallyl group, 3,3-difluoroallyl group, 3, 3-dichloroallyl group, 4,4-difluoro-3-butenyl group, 5,5-difluoro-4-pentenyl group, 6,6-difluoro-5-hexenyl group and the like.

The C2-C6 alkynyl group represents a linear or branched unsaturated hydrocarbon group having one or more triple bonds. Specific examples of C2-C6 alkynyl groups include ethynyl, 1-propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl and 3-pentynyl. group, 4-pentynyl group, 1,1-dimethyl-2-propynyl group, 1-hexynyl group, 2-hexynyl group, 3-hexynyl group, 4-hexynyl group, 5-hexynyl group and the like.

The C2-C6 haloalkynyl group represents a C2-C6 alkynyl group in which hydrogen atoms in the above C2-C6 alkynyl group are optionally substituted with one or more halogen atoms. When substituted with two or more halogen atoms, those halogen atoms may be the same or different, and the number of substitutions is not particularly limited as long as they can exist as substituents.

Specific examples of C2-C6 haloalkynyl groups include 2-fluoroethynyl, 2-chloroethynyl, 2-bromoethynyl, 2-iodoethynyl, 3,3-difluoro-1-propynyl, 3-chloro -3,3-difluoro-1-propynyl group, 3-bromo-3,3-difluoro-1-propynyl group, 3,3,3-trifluoro-1-propynyl group, 4,4-difluoro-1-butynyl group, 4,4-difluoro-2-butynyl group, 4-chloro-4,4-difluoro-1-butynyl group, 4-chloro-4,4-difluoro-2-butynyl group, 4-bromo-4,4 -difluoro-1-butynyl group, 4-bromo-4,4-difluoro-2-butynyl group, 4,4,4-trifluoro-1-butynyl group, 4,4,4-trifluoro-2-butynyl group , 5,5-difluoro-3-pentynyl group, 5-chloro-5,5-difluoro-3-pentynyl group, 5-bromo-5,5-difluoro-3-pentynyl group, 5,5,5-trifluoro -3-pentynyl group, 6,6-difluoro-4-hexynyl group, 6-chloro-6,6-difluoro-4-hexynyl group, 6-bromo-6,6-difluoro-4-hexynyl group, 6,6 , 6-trifluoro-4-hexynyl group and the like.

The C1-C6 alkoxy group represents a C1-C6 alkyl group bonded via an oxygen atom. Specific examples of C1 to C6 alkoxy groups include methoxy, ethoxy, propyloxy, isopropyloxy, butoxy, isobutoxy, sec-butoxy, t-butoxy, pentyloxy, and isopentyloxy. group, 1-methylbutoxy group, 2-methylbutoxy group, neopentyloxy group, 1-ethylpropyloxy group, 1,2-dimethylpropyloxy group, hexyloxy group, 1-methylpentyloxy group, 2-methylpentyl oxy group, 3-methylpentyloxy group, 4-methylpentyloxy group, 1,1-dimethylbutoxy group, 2,2-dimethylbutoxy group, 3,3-dimethylbutoxy group, 1,2-dimethylbutoxy group, 1 ,3-dimethylbutoxy group, 2,3-dimethylbutoxy group, 2-ethylbutoxy group, 1-isopropylpropyloxy group, 1,1,2-trimethylpropyloxy group, 1,2,2-trimethylpropyloxy group, etc. is mentioned.

The C1-C6 haloalkoxy group represents a C1-C6 alkoxy group in which hydrogen atoms in the above-mentioned C1-C6 alkoxy groups are optionally substituted with one or more halogen atoms. When substituted with two or more halogen atoms, those halogen atoms may be the same or different, and the number of substitutions is not particularly limited as long as they can exist as substituents.

Specific examples of C1 to C6 haloalkoxy groups include difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2 -trifluoroethoxy group, 1,1,2,2-tetrafluoroethoxy group, pentafluoroethoxy group, 2,2,2-trichloroethoxy group, 3,3-difluoropropyloxy group, 3,3,3-tri fluoropropyloxy group, heptafluoropropyloxy group, heptafluoroisopropyloxy group, 2,2,2-trifluoro-1-(trifluoromethyl)-ethoxy group, nonafluorobutoxy group, nonafluoro-sec-butoxy group, 3 , 3,4,4,5,5,5-heptafluoropentyloxy group, undecafluoropentyloxy group, tridecafluorohexyloxy group and the like.

The C3-C8 cycloalkoxy group represents a C3-C8 cycloalkyl group bonded via an oxygen atom. Specific examples of the C3-C8 cycloalkoxy groups include cyclopropyloxy, cyclobutoxy, cyclopentyloxy, cyclohexyloxy, cycloheptyloxy, cyclooctyloxy and the like.

The C2-C6 alkenyloxy group represents a C2-C6 alkenyl group bonded via an oxygen atom. In addition, when there is a geometric isomer, it is either the E isomer or the Z isomer alone, or a mixture of the E isomer and the Z isomer in an arbitrary ratio, and if it is within the specified carbon number range, it is not particularly limited. never

Specific examples of C2 to C6 alkenyloxy groups include vinyloxy, 1-propenyloxy, allyloxy, 1-butenyloxy, 2-butenyloxy, 3-butenyloxy, 1-pentenyloxy and 2-pentenyloxy groups. , 3-pentenyloxy group, 4-pentenyloxy group, 3-methyl-2-butenyloxy group, 1-hexenyloxy group, 2-hexenyloxy group, 3-hexenyloxy group, 4-hexenyloxy group, 5-hexenyloxy group, 4-methyl-3-pentenyloxy group, 3-methyl-2-pentenyloxy group and the like.

The C2-C6 haloalkenyloxy group represents a C2-C6 alkenyloxy group in which the hydrogen atoms in the above C2-C6 alkenyloxy group are optionally substituted with one or more halogen atoms. When substituted with two or more halogen atoms, those halogen atoms may be the same or different, and the number of substitutions is not particularly limited as long as they can exist as substituents.

Specific examples of C2 to C6 haloalkenyloxy groups include 2-fluorovinyloxy, 2,2-difluorovinyloxy, 2,2-dichlorovinyloxy, 3-fluoroallyloxy, and 3,3-difluoro allyloxy group, 3,3-dichloroallyloxy group, 4,4-difluoro-3-butenyloxy group, 5,5-difluoro-4-pentenyloxy group, 6,6-difluoro-5-hexenyloxy group and the like. be done.

The C3-C6 alkynyloxy group represents a C3-C6 alkynyl group bonded via an oxygen atom among the above-mentioned C2-C6 alkynyl groups. Specific examples of C3-C6 alkynyloxy groups include propargyloxy, 2-butynyloxy, 3-butynyloxy, 2-pentynyloxy, 3-pentynyloxy, 4-pentynyloxy, 1,1 -dimethyl-2-propynyloxy group, 2-hexynyloxy group, 3-hexynyloxy group, 4-hexynyloxy group, 5-hexynyloxy group and the like.

The C3-C6 haloalkynyloxy group represents a C3-C6 alkynyloxy group in which hydrogen atoms in the above-mentioned C3-C6 alkynyloxy group are optionally substituted with one or more halogen atoms. When substituted with two or more halogen atoms, those halogen atoms may be the same or different, and the number of substitutions is not particularly limited as long as they can exist as substituents.

Specific examples of C3-C6 haloalkynyloxy groups include 1,1-difluoro-2-propynyloxy group, 4,4-difluoro-2-butynyloxy group and 4-chloro-4,4-difluoro-2-butynyloxy group. , 4-bromo-4,4-difluoro-2-butynyloxy group, 4,4,4-trifluoro-2-butynyloxy group, 5,5-difluoro-3-pentynyloxy group, 5-chloro-5,5 -difluoro-3-pentynyloxy group, 5-bromo-5,5-difluoro-3-pentynyloxy group, 5,5,5-trifluoro-3-pentynyloxy group, 6,6-difluoro-4 -hexynyloxy group, 6-chloro-6,6-difluoro-4-hexynyloxy group, 6-bromo-6,6-difluoro-4-hexynyloxy group, 6,6,6-trifluoro-4-hexynyloxy group and the like. be done.

The C2-C6 alkoxyalkoxy group is a C1-C6 alkoxy group in which hydrogen atoms in the C1-C5 alkoxy group are optionally substituted with one or more C1-C5 alkoxy groups. represents There is no particular limitation as long as the total number of carbon atoms is within the specified carbon number range.

Specific examples of C2-C6 alkoxyalkoxy groups include methoxymethoxy, ethoxymethoxy, propyloxymethoxy, isopropyloxymethoxy, methoxyethoxy, ethoxyethoxy, propyloxyethoxy, isopropyloxyethoxy, and methoxypropyl. oxy group, ethoxypropyloxy group, propyloxypropyloxy group, isopropyloxypropyloxy group and the like.

An aryl group represents a cyclic aromatic substituent composed of hydrogen and carbon atoms. Specific examples of aryl groups include a phenyl group and a naphthyl group.

A heteroaryl group is a cyclic aromatic substituent selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom and containing at least one heteroatom as a ring-constituting atom.

Specific examples of heteroaryl groups include pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, tetrazinyl, thienyl, thiazolyl, isothiazolyl, thiadiazolyl, furyl, pyrrolyl, imidazolyl, pyrazolyl, oxazolyl group, isoxazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group, tetrazolyl group and the like.

An aryloxy group represents the above aryl group bonded via an oxygen atom. Specific examples of aryloxy groups include a phenoxy group and a naphthyloxy group.

A heteroaryloxy group represents the above heteroaryl group bonded via an oxygen atom.

Specific examples of heteroaryloxy groups include pyridyloxy, pyridazinyloxy, pyrimidinyloxy, pyrazinyloxy, triazinyloxy, tetrazinyloxy, thienyloxy, thiazolyloxy, and isothiazolyloxy. group, thiadiazolyloxy group, furyloxy group, pyrrolyloxy group, imidazolyloxy group, pyrazolyloxy group, oxazolyloxy group, isoxazolyloxy group, triazolyloxy group, oxadiazolyloxy group, thiadiazolyl oxy group, tetrazolyloxy group and the like.

An aralkyloxy group is an aralkyl group in which a hydrogen atom in a C1 to C3 alkyl group is substituted with an aryl group such as a phenyl group or a naphthyl group, bonded via an oxygen atom. Specific examples of aralkyloxy groups include benzyloxy, phenethyloxy, phenylpropyloxy, naphthalenylmethoxy, naphthalenylethoxy and naphthalenylpropoxy groups.

Specific examples of 3- to 6-membered ring groups containing 1-2 oxygen atoms include 1,2-epoxyethanyl, oxetanyl, oxolanyl, oxanyl, 1,3-dioxolanyl, 1,3- dioxanyl group, 1,4-dioxanyl group and the like.

The compound of the present invention includes a nitrogen-containing heterocyclic compound represented by the following formula (1) or a salt thereof.

以下、式（１）について説明する。

Formula (1) will be described below.

R1 in formula (1) is a hydroxyl group, a cyano group, a C1-C6 alkyl group optionally substituted with a substituent A, a C1-C6 haloalkyl group optionally substituted with a substituent A, a C3-C8 optionally substituted with a substituent A a cycloalkyl group of, a C2 to C6 alkenyl group optionally substituted with a substituent A,
a C2-C6 haloalkenyl group, a C2-C6 alkynyl group optionally substituted with a substituent A, a C2-C6 haloalkynyl group, a C1-C6 alkoxy group optionally substituted with a substituent A, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group optionally substituted with substituent A, C2-C6 alkenyloxy group optionally substituted with substituent A, C2-C6 haloalkenyl an oxy group, a C3-C6 alkynyloxy group optionally substituted with a substituent A, a C3-C6 haloalkynyloxy group, or RaRbN— (wherein Ra and Rb are each independently a hydrogen atom , a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group, or Ra and Rb together with the binding nitrogen atom to form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, a piperidinyl group, a homopiperidinyl group, or an azocanyl group).

Among them, R1 is a cyano group, a C1 to C6 alkyl group optionally substituted with a substituent A,
a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with a substituent A, a C2-C6 alkenyl group optionally substituted with a substituent A, a C2-C6 haloalkenyl group, A C2-C6 alkynyl group or a C2-C6 haloalkynyl group optionally substituted with a substituent A is preferred,
In particular, a C1-C6 alkyl group optionally substituted with a substituent A or a C1-C6 haloalkyl group is preferred.

R1 in formula (1) includes a hydroxyl group and a cyano group.

The C1-C6 alkyl group of the "C1-C6 alkyl group optionally substituted with a substituent A" for R1 in formula (1) has the same definition as above, preferably a methyl group or an ethyl group. , propyl group, isopropyl group, butyl group or isobutyl group, more preferably methyl group, ethyl group, propyl group or isobutyl group, particularly preferably methyl group, ethyl group or isobutyl group. . When having a substituent A, a hydrogen atom in the C1-C6 alkyl group is optionally substituted by the substituent A.

The "C1-C6 haloalkyl group" for R1 in formula (1) has the same meaning as defined above, preferably 2-fluoroethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoro ethyl group, 3,3-difluoropropyl group or 3,3,3-trifluoropropyl group, more preferably 2-fluoroethyl group, 2,2-difluoroethyl group or 2,2,2- A trifluoroethyl group, particularly preferably a 2,2-difluoroethyl group.

The C3-C8 cycloalkyl group of the "C3-C8 cycloalkyl group optionally substituted with a substituent A" in R1 of formula (1) has the same meaning as defined above, preferably a cyclopropyl group. , cyclobutyl group, cyclopentyl group or cyclohexyl group, more preferably cyclopropyl group or cyclobutyl group. A hydrogen atom in the C3-C8 cycloalkyl group is optionally replaced by the substituent A, if the substituent A is present.

The C2-C6 alkenyl group of the "C2-C6 alkenyl group optionally substituted with a substituent A" in R1 of formula (1) has the same meaning as defined above, preferably a vinyl group, 1- It is a propenyl group or an allyl group, more preferably a vinyl group or an allyl group. A hydrogen atom in the C2-C6 alkenyl group is optionally replaced by the substituent A, if the substituent A is present.

The "C2-C6 haloalkenyl group" for R1 in formula (1) has the same meaning as defined above, preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, a 3-fluoroallyl group, or It is a 3,3-difluoroallyl group, more preferably a 2-fluorovinyl group or a 2,2-difluorovinyl group.

The C2-C6 alkynyl group in the "C2-C6 alkynyl group optionally substituted with a substituent A" for R1 in formula (1) has the same definition as above, preferably a propargyl group, 2- It is a butynyl group or a 3-butynyl group, more preferably a propargyl group. A hydrogen atom in the C2-C6 alkynyl group is optionally replaced by the substituent A, if the substituent A is present.

The “C2-C6 haloalkynyl group” for R1 in formula (1) has the same meaning as defined above, preferably 4,4-difluoro-2-butynyl group, 4-chloro-4,4-difluoro- 2-butynyl group, 4-bromo-4,4-difluoro-2-butynyl group, or 4,4,4-trifluoro-2-butynyl group, more preferably 4,4-difluoro-2-butynyl or 4,4,4-trifluoro-2-butynyl group.

The C1-C6 alkoxy group of the "C1-C6 alkoxy group optionally substituted with a substituent A" in R1 of formula (1) has the same definition as above, preferably a methoxy group or an ethoxy group. , propyloxy, isopropyloxy, butoxy or isobutoxy, more preferably methoxy or ethoxy. When having a substituent A, a hydrogen atom in the C1-C6 alkoxy group is optionally replaced by the substituent A.

The “C1-C6 haloalkoxy group” for R1 in formula (1) has the same definition as above, preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, 2,2, 2-trifluoroethoxy group, 3,3-difluoropropyloxy group or 3,3,3-trifluoropropyloxy group, more preferably difluoromethoxy group, trifluoromethoxy group and 2,2-difluoroethoxy or a 2,2,2-trifluoroethoxy group.

The C3-C8 cycloalkoxy group of the "C3-C8 cycloalkoxy group optionally substituted with a substituent A" for R1 in formula (1) has the same definition as above, preferably cyclopropyloxy group, cyclobutoxy group, cyclopentyloxy group or cyclohexyloxy group, more preferably cyclopropyloxy group or cyclobutoxy group. A hydrogen atom in the C3-C8 cycloalkoxy group is optionally replaced by the substituent A, if the substituent A is present.

The C2-C6 alkenyloxy group in the "C2-C6 alkenyloxy group optionally substituted with a substituent A" in R1 of formula (1) has the same definition as above, preferably a vinyloxy group, It is a 1-propenyloxy group or an allyloxy group, more preferably a vinyloxy group. When having a substituent A, a hydrogen atom in the C2-C6 alkenyloxy group is optionally replaced by the substituent A.

The "C2-C6 haloalkenyloxy group" for R1 in formula (1) has the same meaning as defined above, preferably a 2-fluorovinyloxy group, a 2,2-difluorovinyloxy group, a 3-fluoro It is an allyloxy group or a 3,3-difluoroallyloxy group, more preferably a 2-fluorovinyloxy group or a 2,2-difluorovinyloxy group.

The C3-C6 alkynyloxy group in the "C3-C6 alkynyloxy group optionally substituted with a substituent A" in R1 of formula (1) has the same definition as above, preferably a propargyloxy group. , 2-butynyloxy, or 3-butynyloxy, more preferably propargyloxy. A hydrogen atom in the C3-C6 alkynyloxy group is optionally replaced by the substituent A, if the substituent A is present.

The “C3-C6 haloalkynyloxy group” for R1 in formula (1) has the same meaning as defined above, preferably 4,4-difluoro-2-butynyloxy group, 4-chloro-4,4- difluoro-2-butynyloxy group, 4-bromo-4,4-difluoro-2-butynyloxy group, or 4,4,4-trifluoro-2-butynyloxy group, more preferably 4,4-difluoro-2 -butynyloxy group, or 4,4,4-trifluoro-2-butynyloxy group.

“RaRbN—” for R1 in formula (1) (wherein Ra and Rb are each independently a hydrogen atom, a C1 to C6 alkyl group optionally substituted with a substituent B, a C1 to C6 represents a haloalkyl group or a C3-C8 cycloalkyl group, or Ra and Rb, together with the nitrogen atom to which they are attached, represent an aziridinyl group, azetidinyl group, pyrrolidinyl group, piperidinyl group, homopiperidinyl group, or azocanyl group; each term has the same meaning as defined above. Regarding the "C1-C6 alkyl group optionally substituted with a substituent B", when the substituent B is present, the hydrogen atom in the C1-C6 alkyl group is optionally substituted with the substituent B. . Ra and Rb are preferably a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group, more preferably It is a hydrogen atom or a C1-C6 alkyl group optionally substituted with a substituent B. "RaRbN-" is preferably an amino group, methylamino group, ethylamino group, (methoxymethyl)amino group, (2-methoxyethyl)amino group, (cyanomethyl)amino group, (2-cyanoethyl)amino group, dimethylamino group, ethylmethylamino group, diethylamino group, (methoxymethyl)methylamino group, (2-methoxyethyl)methylamino group, (cyanomethyl)methylamino group, (2-cyanoethyl)methylamino group, 2,2- difluoroethylamino group, 2,2,2-trifluoroethylamino group, cyclopropylamino group, (cyclopropyl)methylamino group, pyrrolidinyl group, or piperidinyl group, more preferably dimethylamino group, ethylmethylamino group or a diethylamino group.

R2 in formula (1) is a cyano group, a C1-C6 alkyl group optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 optionally substituted with a substituent A a cycloalkyl group, a C2-C6 alkenyl group optionally substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group optionally substituted with a substituent A, a C2-C6 haloalkynyl group, a C1-C6 alkoxy group optionally substituted with a substituent A, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group optionally substituted with a substituent A, RaRbN-( Here, Ra and Rb are as defined above.), Rx1C(=O)-(wherein Rx1 is a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or RaRbN— (where Ra and Rb are as defined above). ), represents a phenyl group, a 5- to 6-membered heterocyclic group, or an 8- to 10-membered heterocyclic group, and the phenyl group is optionally substituted with 0 to 5 R3 (provided that 2 or more When there is R3, each R3 represents an independent substituent.), the 5- to 6-membered heterocyclic group, or the 8- to 10-membered heterocyclic group is optionally substituted with 0 to 6 R3 (provided that , when there are two or more substituted R3, each R3 represents an independent substituent).

Among them, R2 is a cyano group, a C1-C6 alkyl group optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with a substituent A, a C2-C6 alkenyl group optionally substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group optionally substituted with a substituent A, a C2-C6 haloalkynyl group, a C1-C6 alkoxy group optionally substituted with a substituent A,
C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group optionally substituted with substituent A, RaRbN- (wherein Ra and Rb are as defined above), Rx1C(=O)- (wherein Rx1 has the same definition as above), a phenyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, a tetrazinyl group, a thienyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a thiatriazolyl group, pyrrolyl group, pyrazolyl group, imidazolyl group, triazolyl group, tetrazolyl group, pentazolyl group, furyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, indolyl group, isoindolyl group, indazolyl group, benzimidazolyl group, benzotriazolyl group, benzofuryl group , isobenzofuryl group, benzoxazolyl group, benzothienyl group, benzothiazolyl group, benzoisothiazolyl group, benzothiadiazolyl group, indolizinyl group, imidazopyridyl group, pyrazolopyridyl group, triazolopyridyl group, pyrrolopyrimidinyl group group, imidazopyrimidinyl group, pyrazolopyrimidinyl group, triazolopyrimidinyl group, pyrrolopyrazinyl group, imidazopyrazinyl group, pyrazolopyrazinyl group, triazolopyrazinyl group, quinolyl group, isoquinolyl group, cinolyl group, phthalazinyl group , is preferably a quinoxalinyl group, a quinazolinyl group, or a naphthyridinyl group, and the phenyl group is appropriately substituted with 0 to 5 R3 (provided that when there are two or more R3s, each R3 represents an independent substituent), The pyridyl group, the pyridazinyl group, the pyrimidinyl group, the pyrazinyl group, the triazinyl group, or the tetrazinyl group is optionally substituted with 0 to 4 R3 (provided that when there are two or more substituted R3, each R3 is independently ), the thienyl group, the thiazolyl group, the isothiazolyl group, the thiadiazolyl group, or the thiatriazolyl group, optionally substituted with 0 to 3 R3 (provided that when there are two or more R3 substitutions, Each R3 represents an independent substituent.), the pyrrolyl group, the pyrazolyl group, the imidazolyl group, the triazolyl group, the tetrazolyl group, or the pentazolyl group is optionally substituted with 0 to 4 R3 (provided that 2 When there are substituted or more R3, each R3 represents an independent substituent.), the furyl group, the oxazolyl group, the isoxazolyl group, or the oxadiazolyl group, wherein R3 is optionally 0 ~3 substituted (provided that when there are two or more R3 substituted, each R3 represents an independent substituent. ), the indolyl group, the isoindolyl group, the indazolyl group, the benzimidazolyl group, or the benzotriazolyl group, optionally substituted by 0 to 6 R3 (provided that when there are two or more substituted R3, each R3 is represents an independent substituent.), the benzofuryl group, the isobenzofuryl group, or the benzoxazolyl group is optionally substituted with 0 to 5 R3 (provided that when there are two or more substituted R3, R3 is Each represents an independent substituent.), the benzothienyl group, the benzothiazolyl group, the benzoisothiazolyl group, or the benzothiadiazolyl group is optionally substituted by 0 to 5 R3 (provided that the When R3 is present, each R3 represents an independent substituent.), the indolizinyl group, the imidazopyridyl group, the pyrazolopyridyl group, or the triazolopyridyl group is optionally substituted with 0 to 6 R3 (with the proviso that , when there are two or more R3 substituted, each R3 represents an independent substituent), the pyrrolopyrimidinyl group, the imidazopyrimidinyl group, the pyrazolopyrimidinyl group, the triazolopyrimidinyl group, the pyrrolopyrazinyl group, the imidazo The pyrazinyl group, the pyrazolopyrazinyl group, or the triazolopyrazinyl group is optionally substituted with 0 to 5 R3s (provided that when there are two or more R3s, each R3 is an independent substituent ), the quinolyl group, the isoquinolyl group, the cinolyl group, the phthalazinyl group, the quinoxalinyl group, the quinazolinyl group, or the naphthyridinyl group, where R3 is optionally substituted with 0 to 6 (provided that 2 or more When R3 is present, each R3 represents an independent substituent.).

Further, R2 is a C1-C6 alkyl group optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with a substituent A, a substituent A A C1-C6 alkoxy group optionally substituted with a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group optionally substituted with a substituent A, RaRbN— (wherein Ra and Rb are as defined above), Rx1C(=O)- (wherein Rx1 is as defined above), phenyl group, pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, tetrazinyl group, thienyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, thiatriazolyl group, pyrrolyl group, pyrazolyl group, imidazolyl group, triazolyl group, tetrazolyl group, pentazolyl group, furyl group, oxazolyl group, isoxazolyl group, or oxadiazolyl group, and the phenyl group is optionally substituted with 0 to 5 R3 (provided that when there are two or more R3, each R3 represents an independent substituent), the pyridyl group, the pyridazinyl group, the pyrimidinyl group, the pyrazinyl group, The triazinyl group or the tetrazinyl group is optionally substituted with 0 to 4 R3 (provided that when there are two or more R3s, each R3 represents an independent substituent), the thienyl group, the thiazolyl group, The isothiazolyl group, the thiadiazolyl group, or the thiatriazolyl group is optionally substituted with 0 to 3 R3 (provided that when there are two or more R3s, each R3 represents an independent substituent), the pyrrolyl group, The pyrazolyl group, the imidazolyl group, the triazolyl group, the tetrazolyl group, or the pentazolyl group is optionally substituted with 0 to 4 R3 (provided that when there are two or more R3 substituted, each R3 is an independent substituent. ), the furyl group, the oxazolyl group, the isoxazolyl group, or the oxadiazolyl group is optionally substituted with 0 to 3 R3s (provided that when there are two or more R3s, each R3 is an independent substituent show.).

In particular, R2 is a C1-C6 alkyl group optionally substituted with a substituent A, a C1-C6 haloalkyl group, Rx1C(=O)- (wherein Rx1 is as defined above), or A phenyl group is preferred. The phenyl group is optionally substituted with 0 to 5 R3 (provided that when there are two or more substituted R3s, each R3 represents an independent substituent).
Among them, R2 is preferably a C1-C6 alkyl group optionally substituted with a substituent A, Rx1C(=O)- (wherein Rx1 is as defined above), or a phenyl group. The phenyl group is optionally substituted with 0 to 5 R3 (provided that when there are two or more substituted R3s, each R3 represents an independent substituent).

R2 in formula (1) includes a cyano group.

The C1-C6 alkyl group of the "C1-C6 alkyl group optionally substituted with a substituent A" for R2 in formula (1) has the same meaning as defined above, and is preferably a methyl group or an ethyl group. , propyl, isopropyl, butyl or isobutyl, more preferably methyl, ethyl, isopropyl or isobutyl, particularly preferably methyl or isopropyl. When having a substituent A, a hydrogen atom in the C1-C6 alkyl group is optionally substituted by the substituent A.

The “C1 to C6 haloalkyl group” for R2 in formula (1) has the same meaning as defined above, preferably difluoromethyl group, trifluoromethyl group, 2,2-difluoroethyl group, 2,2,2 -trifluoroethyl group, 3,3-difluoropropyl group, or 3,3,3-trifluoropropyl group, more preferably difluoromethyl group, trifluoromethyl group, 2,2-difluoroethyl group, or It is a 2,2,2-trifluoroethyl group.

The C3-C8 cycloalkyl group of the "C3-C8 cycloalkyl group optionally substituted with a substituent A" for R2 in formula (1) has the same meaning as defined above, preferably a cyclopropyl group. , cyclobutyl group, cyclopentyl group or cyclohexyl group, more preferably cyclopropyl group, cyclopentyl group or cyclohexyl group. A hydrogen atom in the C3-C8 cycloalkyl group is optionally replaced by the substituent A, if the substituent A is present.

The C2-C6 alkenyl group of the "C2-C6 alkenyl group optionally substituted with a substituent A" for R2 in formula (1) has the same meaning as defined above, preferably a vinyl group, 1- It is a propenyl group or an allyl group, more preferably a vinyl group or an allyl group. A hydrogen atom in the C2-C6 alkenyl group is optionally replaced by the substituent A, if the substituent A is present.

The “C2-C6 haloalkenyl group” for R2 in formula (1) has the same meaning as defined above, preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, a 3-fluoroallyl group, or It is a 3,3-difluoroallyl group, more preferably a 2-fluorovinyl group or a 2,2-difluorovinyl group.

The C2-C6 alkynyl group in the "C2-C6 alkynyl group optionally substituted with a substituent A" for R2 in formula (1) is as defined above, preferably an ethynyl group, 1- It is a propynyl group, propargyl group, 1-butynyl group, 2-butynyl group or 3-butynyl group, more preferably an ethynyl group, 1-propynyl group or propargyl group. A hydrogen atom in the C2-C6 alkynyl group is optionally replaced by the substituent A, if the substituent A is present.

The "C2-C6 haloalkynyl group" for R2 in formula (1) has the same meaning as defined above, preferably 2-fluoroethynyl group, 2-chloroethynyl group, 2-bromoethynyl group, 2-iodo ethynyl group, 3,3-difluoro-1-propynyl group, 3,3,3-trifluoro-1-propynyl group, 4,4-difluoro-1-butynyl group, 4,4-difluoro-2-butynyl group, 4,4,4-trifluoro-1-butynyl group or 4,4,4-trifluoro-2-butynyl group, more preferably 2-fluoroethynyl group and 3,3-difluoro-1-propynyl or a 3,3,3-trifluoro-1-propynyl group.

The C1-C6 alkoxy group of the "C1-C6 alkoxy group optionally substituted with a substituent A" for R2 in formula (1) has the same definition as above, and is preferably a methoxy group or an ethoxy group. , propyloxy, isopropyloxy, butoxy or isobutoxy, more preferably ethoxy, propyloxy, isopropyloxy or isobutoxy. When having a substituent A, a hydrogen atom in the C1-C6 alkoxy group is optionally replaced by the substituent A.

The “C1-C6 haloalkoxy group” for R2 in formula (1) has the same meaning as defined above, preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, 2,2, 2-trifluoroethoxy group, 3,3-difluoropropyloxy group or 3,3,3-trifluoropropyloxy group, more preferably difluoromethoxy group, trifluoromethoxy group and 2,2-difluoroethoxy or a 2,2,2-trifluoroethoxy group.

The C3-C8 cycloalkoxy group of the "C3-C8 cycloalkoxy group optionally substituted with a substituent A" for R2 in formula (1) has the same definition as above, preferably cyclopropyloxy cyclobutoxy group, cyclopentyloxy group or cyclohexyloxy group, more preferably cyclopropyloxy group, cyclopentyloxy group or cyclohexyloxy group. A hydrogen atom in the C3-C8 cycloalkoxy group is optionally replaced by the substituent A, if the substituent A is present.

“RaRbN—” for R2 in formula (1) (where Ra and Rb are each independently a hydrogen atom, a C1 to C6 alkyl group optionally substituted with a substituent B, a C1 to C6 represents a haloalkyl group or a C3-C8 cycloalkyl group, or Ra and Rb, together with the nitrogen atom to which they are attached, represent an aziridinyl group, azetidinyl group, pyrrolidinyl group, piperidinyl group, homopiperidinyl group, or azocanyl group; each term has the same meaning as defined above. Regarding the "C1-C6 alkyl group optionally substituted with a substituent B", when the substituent B is present, the hydrogen atom in the C1-C6 alkyl group is optionally substituted with the substituent B. . Ra and Rb are preferably a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group, more preferably It is a hydrogen atom or a C1-C6 alkyl group optionally substituted with a substituent B. "RaRbN-" is preferably an amino group, methylamino group, ethylamino group, (methoxymethyl)amino group, (2-methoxyethyl)amino group, (cyanomethyl)amino group, (2-cyanoethyl)amino group, dimethylamino group, ethylmethylamino group, diethylamino group, (methoxymethyl)methylamino group, (2-methoxyethyl)methylamino group, (cyanomethyl)methylamino group, (2-cyanoethyl)methylamino group, 2,2- difluoroethylamino group, 2,2,2-trifluoroethylamino group, cyclopropylamino group, (cyclopropyl)methylamino group, pyrrolidinyl group, or piperidinyl group, more preferably dimethylamino group, ethylmethylamino group or a diethylamino group.

"Rx1C(=O)-" for R2 in formula (1) (wherein Rx1 is a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 represents a cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or RaRbN- (wherein Ra and Rb are as defined above). Each term has the same meaning as defined above. Rx1 is preferably a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 halo represents an alkoxy group or RaRbN- (wherein Ra and Rb are as defined above). ), more preferably a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, or a C1-C6 alkoxy group, particularly preferably a C1-C6 It is an alkoxy group. "Rx1C(=O)-" is preferably an acetyl group, a methoxyacetyl group, a cyanoacetyl group, a propionyl group, a difluoroacetyl group, a trifluoroacetyl group, a cyclopropanecarbonyl group, a methoxycarbonyl group, an ethoxycarbonyl group, 2 , 2-difluoroethoxycarbonyl group, 2,2,2-trifluoroethoxycarbonyl group, 3,3,3-trifluoropropyloxycarbonyl group, aminocarbonyl group, methylaminocarbonyl group, ethylaminocarbonyl group, dimethylaminocarbonyl group, ethylmethylaminocarbonyl group, diethylaminocarbonyl group, pyrrolidinylcarbonyl group or piperidinylcarbonyl group, more preferably acetyl group, methoxyacetyl group, cyanoacetyl group, difluoroacetyl group or trifluoroacetyl group , a methoxycarbonyl group, or an ethoxycarbonyl group, and particularly preferably an ethoxycarbonyl group.

R2 in formula (1) includes a phenyl group. The phenyl group is optionally substituted with 0 to 5 R3s (provided that when there are two or more R3s substituted, each R3 represents an independent substituent).
A phenyl group for R2 in formula (1) (the phenyl group is suitably substituted with 0 to 5 R3s (provided, however, that when there are two or more R3s, each R3 represents an independent substituent.) is preferably is a phenyl group, 2-fluorophenyl group, 2-chlorophenyl group, 2-bromophenyl group, 2-iodophenyl group, 2-methylphenyl group, 2-methoxyphenyl group, 3-fluorophenyl group, 3-chlorophenyl group , 3-bromophenyl group, 3-iodophenyl group, 3-methylphenyl group, 3-methoxyphenyl group, 4-chlorophenyl group, 4-bromophenyl group, 4-iodophenyl group, 4-methylphenyl group, 4- methoxyphenyl group, 2,3-difluorophenyl group, 2,4-difluorophenyl group, 2,5-difluorophenyl group, 2,6-difluorophenyl group, 2-chloro-3-fluorophenyl group, 2-chloro- 4-fluorophenyl group, 2-chloro-5-fluorophenyl group, 2-chloro-6-fluorophenyl group, 2-bromo-3-fluorophenyl group, 2-bromo-4-fluorophenyl group, 2-bromo- 5-fluorophenyl group, 2-bromo-6-fluorophenyl group, 2-fluoro-3-methylphenyl group, 2-fluoro-4-methylphenyl group, 2-fluoro-5-methylphenyl group, 2-fluoro- 6-methylphenyl group, 2-chloro-3-methylphenyl group, 2-chloro-4-methylphenyl group, 2-chloro-5-methylphenyl group, 2-chloro-6-methylphenyl group, 2-bromo- 3-methylphenyl group, 2-bromo-4-methylphenyl group, 2-bromo-5-methylphenyl group, 2-bromo-6-methylphenyl group, 2,3-dimethylphenyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 2,6-dimethylphenyl group, 2-fluoro-3-methoxyphenyl group, 2-fluoro-4-methoxyphenyl group, 2-fluoro-5-methoxyphenyl group, 2- fluoro-6-methoxyphenyl group, 2-chloro-3-methoxyphenyl group, 2-chloro-4-methoxyphenyl group, 2-chloro-5-methoxyphenyl group, 2-chloro-6-methoxyphenyl group, 2- bromo-3-methoxyphenyl group, 2-bromo-4-methoxyphenyl group, 2-bromo-5-methoxyphenyl group, 2-bromo-6-methoxyphenyl group, 2,3,4-trifluorophenyl group, 2 , 3,5-trifle orophenyl group, 2,3,6-trifluorophenyl group, 2-chloro-3,4-difluorophenyl group, 2-chloro-3,5-difluorophenyl group, 2-chloro-3,6-difluorophenyl group, 2-bromo-3,4-difluorophenyl group, 2-bromo-3,5-difluorophenyl group, 2-bromo-3,6-difluorophenyl group, 2-fluoro-3,4-dimethoxyphenyl group, 2 -fluoro-3,5-dimethoxyphenyl group, 2-fluoro-3,6-dimethoxyphenyl group, 2-chloro-3,4-dimethoxyphenyl group, 2-chloro-3,5-dimethoxyphenyl group, 2-chloro -3,6-dimethoxyphenyl group, 2-bromo-3,4-dimethoxyphenyl group, 2-bromo-3,5-dimethoxyphenyl group, or 2-bromo-3,6-dimethoxyphenyl group, more preferably is a phenyl group, 2-fluorophenyl group, 2-chlorophenyl group, 2-bromophenyl group, 2-iodophenyl group, 2-methoxyphenyl group, 3-fluorophenyl group, 3-chlorophenyl group, 3-bromophenyl group , 3-iodophenyl group, 3-methoxyphenyl group, 4-chlorophenyl group, 4-bromophenyl group, 4-iodophenyl group, 4-methoxyphenyl group, 2,3-difluorophenyl group, 2,4-difluorophenyl group, 2,5-difluorophenyl group, 2,6-difluorophenyl group, 2-chloro-3-fluorophenyl group, 2-chloro-4-fluorophenyl group, 2-chloro-5-fluorophenyl group, 2- chloro-6-fluorophenyl group, 2-bromo-3-fluorophenyl group, 2-bromo-4-fluorophenyl group, 2-bromo-5-fluorophenyl group, 2-bromo-6-fluorophenyl group, 2- fluoro-3-methoxyphenyl group, 2-fluoro-4-methoxyphenyl group, 2-fluoro-5-methoxyphenyl group, 2-fluoro-6-methoxyphenyl group, 2-chloro-3-methoxyphenyl group, 2- chloro-4-methoxyphenyl group, 2-chloro-5-methoxyphenyl group, 2-chloro-6-methoxyphenyl group, 2-bromo-3-methoxyphenyl group, 2-bromo-4-methoxyphenyl group, 2- Bromo-5-methoxyphenyl group, 2-bromo-6-methoxyphenyl group, 2,3,4-trifluorophenyl group, 2,3,5-trifluorophenyl group, 2,3,6-trifluorophenyl group group, 2-chloro-3,4-difluorophenyl group, 2-chloro-3,5-difluorophenyl group, 2-chloro-3,6-difluorophenyl group, 2-bromo-3,4-difluorophenyl group , 2-bromo-3,5-difluorophenyl group, 2-bromo-3,6-difluorophenyl group, , 2-fluoro-3,4-dimethoxyphenyl group, 2-fluoro-3,5-dimethoxyphenyl group, 2-fluoro-3,6-dimethoxyphenyl group, 2-chloro-3,4-dimethoxyphenyl group, 2-chloro-3,5-dimethoxyphenyl group, 2-chloro-3,6-dimethoxyphenyl group, 2- bromo-3,4-dimethoxyphenyl group, 2-bromo-3,5-dimethoxyphenyl group or 2-bromo-3,6-dimethoxyphenyl group, particularly preferably 2-fluorophenyl group and 2-chlorophenyl 2-chloro-5-methoxyphenyl group, or 2-chloro-3,5-difluorophenyl group.

R2 in formula (1) includes a 5- to 6-membered heterocyclic group or an 8- to 10-membered heterocyclic group. The 5- to 6-membered heterocyclic group or the 8- to 10-membered heterocyclic group is optionally substituted with 0 to 6 R3 (provided that when there are 2 or more R3, each R3 is an independent substituent. show.).

Specific examples of 5- to 6-membered heterocyclic groups include pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, tetrazinyl, thienyl, thiazolyl, isothiazolyl, thiadiazolyl, thiatriazolyl, pyrrolyl, A pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, a pentazolyl group, a furyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, and the like.

Specific examples of 8- to 10-membered heterocyclic groups include indolyl group, isoindolyl group, indazolyl group, benzimidazolyl group, benzotriazolyl group, benzofuryl group, isobenzofuryl group, benzoxazolyl group, benzothienyl group, benzothiazolyl group, benzoisothiazolyl group, benzothiadiazolyl group, indolizinyl group, imidazopyridyl group, pyrazolopyridyl group, triazolopyridyl group, pyrrolopyrimidinyl group, imidazopyrimidinyl group, pyrazolopyrimidinyl group, triazolopyrimidinyl group, pyrrolopyrazinyl group, imidazopyrazinyl group, pyrazolopyrazinyl group, triazolopyrazinyl group, quinolyl group, isoquinolyl group, cinolyl group, phthalazinyl group, quinoxalinyl group, quinazolinyl group, naphthyridinyl group, and the like.

Among them, a 5- to 6-membered heterocyclic group is preferable, and specifically, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, a tetrazinyl group, a thienyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, and a thiatriazolyl group. , pyrrolyl group, pyrazolyl group, imidazolyl group, triazolyl group, tetrazolyl group, pentazolyl group, furyl group, oxazolyl group, isoxazolyl group, or oxadiazolyl group,
A pyridyl group, a thienyl group, a pyrrolyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, an oxazolyl group, or an isoxazolyl group is particularly preferred.

The pyridyl group, the pyridazinyl group, the pyrimidinyl group, the pyrazinyl group, the triazinyl group, or the tetrazinyl group is optionally substituted with 0 to 4 R3 (provided that when there are two or more R3 substituted, each R3 is independently represents a substituted group).
The thienyl group, the thiazolyl group, the isothiazolyl group, the thiadiazolyl group, or the thiatriazolyl group is optionally substituted with 0 to 3 R3s (provided that when there are two or more R3s, each R3 is an independent substituent. show.).
The pyrrolyl group, the pyrazolyl group, the imidazolyl group, the triazolyl group, the tetrazolyl group, or the pentazolyl group is optionally substituted with 0 to 4 R3 (provided that when there are two or more R3 substituted, each R3 is independently represents a substituted group).
The furyl group, the oxazolyl group, the isoxazolyl group, or the oxadiazolyl group is optionally substituted with 0 to 3 R3s (provided that when there are two or more R3s, each R3 represents an independent substituent).
The indolyl group, the isoindolyl group, the indazolyl group, the benzimidazolyl group, or the benzotriazolyl group is optionally substituted with 0 to 6 R3s (provided that when there are two or more R3s, each R3 is independently represents a substituent).
The benzofuryl group, the isobenzofuryl group, or the benzoxazolyl group is optionally substituted with 0 to 5 R3 (provided that when there are two or more R3 substituted, each R3 represents an independent substituent). .
The benzothienyl group, the benzothiazolyl group, the benzoisothiazolyl group, or the benzothiadiazolyl group is optionally substituted with 0 to 5 R3 (provided that when there are two or more substituted R3, each R3 is independently represents a substituent).
The indolizinyl group, the imidazopyridyl group, the pyrazolopyridyl group, or the triazolopyridyl group is optionally substituted with 0 to 6 R3 (provided that when there are two or more R3 substituted, each R3 is an independent substituent represents ).
The pyrrolopyrimidinyl group, the imidazopyrimidinyl group, the pyrazolopyrimidinyl group, the triazolopyrimidinyl group, the pyrrolopyrazinyl group, the imidazopyrazinyl group, the pyrazolopyrazinyl group, or the triazolopyrazinyl group , R3 are optionally substituted with 0 to 5 (provided that when there are two or more substituted R3, each R3 represents an independent substituent).
The quinolyl group, the isoquinolyl group, the cinolyl group, the phthalazinyl group, the quinoxalinyl group, the quinazolinyl group, or the naphthyridinyl group is optionally substituted with 0 to 6 R3 (provided that when there are 2 or more R3 substitutions, Each R3 represents an independent substituent.).

The 5- to 6-membered heterocyclic group or the 8- to 10-membered heterocyclic group for R2 in formula (1) will be described in detail below.

で表される部分構造（ここで、Ｒ３は前記と同義であり、ｎａは０～４の整数を表す。）を表す。A) When R2 is a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, or a tetrazinyl group, R2 has the formula (a)

represents a partial structure represented by (here, R3 is as defined above and na represents an integer of 0 to 4).

G1, G2, G3, G4, and G5 in formula (a) each independently represent a carbon atom or a nitrogen atom. However, at least one of G1, G2, G3, G4 and G5 is a nitrogen atom. Any one of G1, G2, G3, G4 and G5 is preferably a nitrogen atom. That is, it is a pyridyl group.

na in the formula (a) represents an integer of 0-4.

When na in formula (a) is 2 or more, 2 or more R3 each represent an independent substituent, may be the same or different, and can be arbitrarily selected.

Specific examples of the partial structure of formula (a) are shown below.

Preferred specific examples of the partial structure of formula (a) are shown below.

More preferred specific examples of the partial structure of formula (a) are shown below.

または式（ｂ－２）

で表される部分構造（ここで、Ｒ３は前記と同義であり、ｎｂは０～３の整数を表す。）を表す。B) When R2 is a thienyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, or a thiatriazolyl group, R2 is represented by formula (b-1)

or formula (b-2)

represents a partial structure represented by (here, R3 is as defined above, and nb represents an integer of 0 to 3).

G6, G7 and G8 in formulas (b-1) and (b-2) each independently represent a carbon atom or a nitrogen atom.

nb in formulas (b-1) and (b-2) represents an integer of 0-3.

When nb in formula (b-1) and formula (b-2) is 2 or more, 2 or more R3 each represent an independent substituent, may be the same or different, and can be arbitrarily selected. .

Specific examples of the partial structure of formula (b-1) are shown below.

Preferred specific examples of the partial structure of formula (b-1) are shown below.

Preferred specific examples of the partial structure of formula (b-1) are shown below.

Specific examples of the partial structure of formula (b-2) are shown below.

Preferred specific examples of the partial structure of formula (b-2) are shown below.

Preferred specific examples of the partial structure of formula (b-2) are shown below.

式（ｃ－２）

または式（ｃ－３）

で表される部分構造（ここで、Ｒ３は前記と同義であり、ｎｃは０～４の整数を表す。）を表す。C) When R2 is a pyrrolyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, or a pentazolyl group, R2 is
Formula (c-1)

Formula (c-2)

or formula (c-3)

represents a partial structure represented by (here, R3 is as defined above, and nc represents an integer of 0 to 4).

G9, G10, G11 and G12 in formulas (c-1), (c-2) and (c-3) each independently represent a carbon atom or a nitrogen atom.

nc in formulas (c-1), (c-2), and (c-3) represents an integer of 0-4.

When nc in formula (c-1), formula (c-2), and formula (c-3) is 2 or more, two or more R3 each represent an independent substituent and may be the same or different, Can be selected arbitrarily.

Specific examples of the partial structure of formula (c-1) are shown below.

Preferred specific examples of the partial structure of formula (c-1) are shown below.

Preferred specific examples of the partial structure of formula (c-1) are shown below.

Specific examples of the partial structure of formula (c-2) are shown below.

Preferred specific examples of the partial structure of formula (c-2) are shown below.

Preferred specific examples of the partial structure of formula (c-2) are shown below.

Specific examples of the partial structure of formula (c-3) are shown below.

Preferred specific examples of the partial structure of formula (c-3) are shown below.

Preferred specific examples of the partial structure of formula (c-3) are shown below.

式（ｄ－２）

式（ｄ－３）

または、式（ｄ－４）

で表される部分構造（ここで、Ｒ３は前記と同義であり、ｎｄは０～３の整数を表す。）を表す。D) when R2 is a furyl group, an oxazolyl group, an isoxazolyl group, or an oxadiazolyl group, R2 is
Formula (d-1)

Formula (d-2)

Formula (d-3)

Or, formula (d-4)

represents a partial structure represented by (here, R3 is as defined above, and nd represents an integer of 0 to 3).

G13 and G14 in formulas (d-1), (d-2), (d-3) and (d-4) each independently represent a carbon atom or a nitrogen atom.

nd in formula (d-1), formula (d-2), formula (d-3), and formula (d-4) represents an integer of 0-3.

When nd in formula (d-1), formula (d-2), formula (d-3), and formula (d-4) is 2 or more, 2 or more R3 each represent an independent substituent, They may be the same or different and can be arbitrarily selected.

式（ｄ－１）の部分構造のうち、好ましい具体例を以下に示す。

Specific examples of the partial structure of formula (d-1) are shown below.

Preferred specific examples of the partial structure of formula (d-1) are shown below.

Preferred specific examples of the partial structure of formula (d-1) are shown below.

式（ｄ－２）の部分構造のうち、好ましい具体例を以下に示す。

Specific examples of the partial structure of formula (d-2) are shown below.

Preferred specific examples of the partial structure of formula (d-2) are shown below.

Preferred specific examples of the partial structure of formula (d-2) are shown below.

式（ｄ－３）の部分構造のうち、好ましい具体例を以下に示す。

Specific examples of the partial structure of formula (d-3) are shown below.

Preferred specific examples of the partial structure of formula (d-3) are shown below.

Preferred specific examples of the partial structure of formula (d-3) are shown below.

式（ｄ－３）の部分構造のうち、好ましい具体例を以下に示す。

Specific examples of the partial structure of formula (d-4) are shown below.

Preferred specific examples of the partial structure of formula (d-3) are shown below.

Preferred specific examples of the partial structure of formula (d-3) are shown below.

または式（ｅ－２）

で表される部分構造（ここで、Ｒ３は前記と同義であり、ｎｅは０～６の整数を表す。）を表す。E) When R2 is an indolyl group, an isoindolyl group, an indazolyl group, a benzimidazolyl group, or a benzotriazolyl group, R2 is represented by formula (e-1)

or formula (e-2)

represents a partial structure represented by (here, R3 has the same meaning as defined above, and ne represents an integer of 0 to 6).

G15 and G16 in formulas (e-1) and (e-2) each independently represent a carbon atom or a nitrogen atom.

ne in the formulas (e-1) and (e-2) represents an integer of 0-6.

When ne in formula (e-1) and formula (e-2) is 2 or more, 2 or more R3 each represent an independent substituent, may be the same or different, and can be arbitrarily selected. .

Specific examples of the partial structure of formula (e-1) are shown below.

Specific examples of the partial structure of formula (e-2) are shown below.

または式（ｆ－２）

で表される部分構造（ここで、Ｒ３は前記と同義であり、ｎｆは０～５の整数を表す。）を表す。F) When R2 is a benzofuryl group, an isobenzofuryl group, or a benzoxazolyl group, R2 is represented by formula (f-1)

or formula (f-2)

represents a partial structure represented by (here, R3 is as defined above, and nf represents an integer of 0 to 5).

G17 in formula (f-1) represents a carbon atom or a nitrogen atom.

nf in formulas (f-1) and (f-2) represents an integer of 0-5.

When nf in formula (f-1) and formula (f-2) is 2 or more, 2 or more R3 each represent an independent substituent, may be the same or different, and can be arbitrarily selected. .

Specific examples of the partial structure of formula (f-1) are shown below.

Specific examples of the partial structure of formula (f-2) are shown below.

または式（ｇ－２）

で表される部分構造（ここで、Ｒ３は前記と同義であり、ｎｇは０～５の整数を表す。）を表す。G) When R2 is a benzothienyl group, a benzothiazolyl group, a benzoisothiazolyl group, or a benzothiadiazolyl group, R2 is represented by formula (g-1)

or formula (g-2)

represents a partial structure represented by (here, R3 is as defined above, and ng represents an integer of 0 to 5).

G18 and G19 in formulas (g-1) and (g-2) each independently represent a carbon atom or a nitrogen atom.

ng in the formulas (g-1) and (g-2) represents an integer of 0-5.

When ng in formula (g-1) and formula (g-2) is 2 or more, 2 or more R3 each represent an independent substituent, may be the same or different, and can be arbitrarily selected. .

Specific examples of the partial structure of formula (g-1) are shown below.

Specific examples of the partial structure of formula (g-2) are shown below.

で表される部分構造（ここで、Ｒ３は前記と同義であり、ｎｈは０～６の整数を表す。）を表す。H) When R2 is an indolizinyl group, an imidazopyridyl group, a pyrazolopyridyl group, or a triazolopyridyl group, R2 is represented by formula (h-1)

represents a partial structure represented by (here, R3 is as defined above, and nh represents an integer of 0 to 6).

G20, G21 and G22 in formula (h-1) each independently represent a carbon atom or a nitrogen atom.

nh in the formula (h-1) represents an integer of 0-6.

When nh in formula (h-1) is 2 or more, 2 or more R3 each represent an independent substituent, may be the same or different, and can be arbitrarily selected.

Specific examples of the partial structure of formula (h-1) are shown below.

式（ｉ－２）

または式（ｉ－３）

で表される部分構造（ここで、Ｒ３は前記と同義であり、ｎｉは０～５の整数を表す。）を表す。I) When R2 is a pyrrolopyrimidinyl group, imidazopyrimidinyl group, pyrazolopyrimidinyl group, triazolopyrimidinyl group, pyrrolopyrazinyl group, imidazopyrazinyl group, pyrazolopyrazinyl group, or triazolopyrazinyl group, R2 is the formula (i-1)

Formula (i-2)

or formula (i-3)

represents a partial structure represented by (here, R3 is as defined above, and ni represents an integer of 0 to 5).

G23, G24 and G25 in formulas (i-1), (i-2) and (i-3) each independently represent a carbon atom or a nitrogen atom.

ni in formula (i-1), formula (i-2) and formula (i-3) represents an integer of 0-5.

When ni in formula (i-1), formula (i-2) and formula (i-3) is 2 or more, two or more R3 each represent an independent substituent, which may be the same or different, and optionally can be selected to

Specific examples of the partial structure of formula (i-1) are shown below.

Specific examples of the partial structure of formula (i-2) are shown below.

Specific examples of the partial structure of formula (i-3) are shown below.

または式（ｊ－２）

で表される部分構造（ここで、Ｒ３は前記と同義であり、ｎｊは０～６の整数を表す。）を表す。J) When R2 is a quinolyl group, isoquinolyl group, cinolyl group, phthalazinyl group, quinoxalinyl group, quinazolinyl group, or naphthyridinyl group, R2 is represented by formula (j-1)

or formula (j-2)

represents a partial structure represented by (here, R3 has the same meaning as defined above, and nj represents an integer of 0 to 6).

G26, G27, G28 and G29 in formula (j-1) and formula (j-2) each independently represent a carbon atom or a nitrogen atom. However, at least one of G26, G27, G28 and G29 is a nitrogen atom. In formula (j-1), any one of G26, G27, G28 and G29 is preferably a nitrogen atom among G26, G27, G28 and G29. That is, it is a quinolyl group.

nj in formula (j-1) and formula (j-2) represents an integer of 0-6.

When nj in formula (j-1) and formula (j-2) is 2 or more, two or more R3 each represent an independent substituent, may be the same or different, and can be arbitrarily selected. .

Specific examples of the partial structure of formula (j-1) are shown below.

Specific examples of the partial structure of formula (j-2) are shown below.

R3 is a hydroxyl group, a cyano group, a nitro group, a halogen atom, a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group optionally substituted with a substituent C, a C3- C8 cycloalkyl group, C2-C6 alkenyl group optionally substituted with substituent C, C2-C6 haloalkenyl group, C2-C6 alkynyl group optionally substituted with substituent C, C2-C6 A haloalkynyl group, a C1 to C6 alkoxy group optionally substituted with a substituent C, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group optionally substituted with a substituent C, a substituent C2-C6 alkenyloxy group optionally substituted with C, C2-C6 haloalkenyloxy group, C3-C6 alkynyloxy group optionally substituted with substituent C, C3-C6 haloalkynyloxy group group, an aryl group optionally substituted with a substituent D, a heteroaryl group optionally substituted with a substituent D, an aryloxy group optionally substituted with a substituent D, an aryloxy group optionally substituted with a substituent D a heteroaryloxy group optionally substituted with a substituent D, an aralkyloxy group optionally substituted with a substituent D, RaRbN- (where Ra and Rb are as defined above), Rc-L- (where Rc represents a C1-C6 alkyl group or a C1-C6 haloalkyl group, and L represents S, SO, or SO2.), _Rx1C (=O)- (wherein Rx1 has the same ), Rx1C (=O) O- (where Rx1 has the same definition as above), Rx2C (=O) N (Rx3)- (where Rx2 is a hydrogen atom, a substituent B as appropriate optionally substituted C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group, or RaRbN- (wherein Ra and Rb are as defined above), Rx3 is a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl or a C3-C8 cycloalkyl group), Rx4Rx5C=NO- (wherein Rx4 and Rx5 are each independently a hydrogen atom, optionally substituted with a substituent B C1 -C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, A C3-C8 cycloalkoxy group, or RaRbN— (wherein Ra and Rb are as defined above. ). ), or a 3- to 6-membered ring group containing 1 to 2 oxygen atoms.

Among them, R3 is a hydroxyl group, a cyano group, a halogen atom, a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group optionally substituted with a substituent C, a C3-C8 optionally substituted with a substituent C a cycloalkyl group, a C2 to C6 alkenyl group optionally substituted with a substituent C, a C2 to C6 alkynyl group optionally substituted with a substituent C, a C1 optionally substituted with a substituent C to C6 alkoxy group, C1 to C6 haloalkoxy group, C3 to C8 cycloalkoxy group optionally substituted by substituent C, C2 to C6 alkenyloxy group optionally substituted by substituent C, A C2 to C6 haloalkenyloxy group, a C3 to C6 alkynyloxy group optionally substituted with a substituent C, or a C3 to C6 haloalkynyloxy group are preferred,
Furthermore, a halogen atom, a C1-C6 alkyl group optionally substituted with a substituent C, or a C1-C6 alkoxy group optionally substituted with a substituent C is preferred,
In particular, a halogen atom or a C1-C6 alkoxy group optionally substituted with a substituent C is preferred.

R3 in formula (1) includes a hydroxyl group, a cyano group and a nitro group.

The halogen atom for R3 in formula (1) has the same definition as above, preferably a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, more preferably a fluorine atom or a chlorine atom.

The C1-C6 alkyl group of the "C1-C6 alkyl group optionally substituted with a substituent C" for R3 in formula (1) has the same definition as above, preferably a methyl group or an ethyl group. , propyl group or isopropyl group, more preferably methyl group or ethyl group. When having a substituent C, a hydrogen atom in the C1-C6 alkyl group is optionally replaced by the substituent C.

The “C1-C6 haloalkyl group” for R3 in formula (1) has the same meaning as defined above, preferably difluoromethyl group, trifluoromethyl group, 2,2-difluoroethyl group, 2,2,2 -trifluoroethyl group, 3,3-difluoropropyl group, or 3,3,3-trifluoropropyl group, more preferably difluoromethyl group, trifluoromethyl group, 2,2-difluoroethyl group, or It is a 2,2,2-trifluoroethyl group.

The C3-C8 cycloalkyl group of the "C3-C8 cycloalkyl group optionally substituted with a substituent C" for R3 in formula (1) has the same definition as above, preferably a cyclopropyl group. , cyclobutyl group, cyclopentyl group or cyclohexyl group, more preferably cyclopropyl group or cyclobutyl group. A hydrogen atom in the C3-C8 cycloalkyl group is optionally replaced by a substituent C, if it has a substituent C.

The C2-C6 alkenyl group of the "C2-C6 alkenyl group optionally substituted with a substituent C" in R3 of formula (1) has the same definition as above, preferably a vinyl group, 1- It is a propenyl group, allyl group, 1-butenyl group, 2-butenyl group or 3-butenyl group, more preferably vinyl group, 1-propenyl group or allyl group. If a substituent C is present, a hydrogen atom in the C2-C6 alkenyl group is optionally replaced by the substituent C.

The “C2-C6 haloalkenyl group” for R3 in formula (1) has the same meaning as defined above, and is preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, or a 2,2-dichlorovinyl group. , 3-fluoroallyl group, 3,3-difluoroallyl group or 3,3-dichloroallyl group, more preferably 2-fluorovinyl group or 2,2-difluorovinyl group.

The C2-C6 alkynyl group of the "C2-C6 alkynyl group optionally substituted with a substituent C" in R3 of formula (1) has the same meaning as defined above, preferably an ethynyl group, 1- It is a propynyl group, propargyl group, 1-butynyl group, 2-butynyl group or 3-butynyl group, more preferably an ethynyl group or propargyl group. When having a substituent C, a hydrogen atom in the C2-C6 alkynyl group is optionally replaced by the substituent C.

The “C2-C6 haloalkynyl group” for R3 in formula (1) has the same meaning as defined above, preferably 3,3-difluoro-1-propynyl group, 3,3,3-trifluoro-1 -propynyl group, 4,4-difluoro-1-butynyl group, 4,4-difluoro-2-butynyl group, 4,4,4-trifluoro-1-butynyl group, or 4,4,4-trifluoro- It is a 2-butynyl group, more preferably a 3,3-difluoro-1-propynyl group or a 3,3,3-trifluoro-1-propynyl group.

The C1-C6 alkoxy group of the "C1-C6 alkoxy group optionally substituted with a substituent C" for R3 in formula (1) has the same definition as above, preferably a methoxy group or an ethoxy group. , propyloxy, isopropyloxy, butoxy or isobutoxy, more preferably methoxy, ethoxy, propyloxy or isopropyloxy, particularly preferably methoxy. When having a substituent C, a hydrogen atom in the C1-C6 alkoxy group is optionally replaced by the substituent C.

The “C1-C6 haloalkoxy group” for R3 in formula (1) has the same meaning as defined above, preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, 2,2, 2-trifluoroethoxy group, 3,3-difluoropropyloxy group or 3,3,3-trifluoropropyloxy group, more preferably difluoromethoxy group, trifluoromethoxy group and 2,2-difluoroethoxy or a 2,2,2-trifluoroethoxy group.

The C3-C8 cycloalkoxy group in the "C3-C8 cycloalkoxy group optionally substituted with a substituent C" for R3 in formula (1) has the same definition as above, preferably cyclopropyloxy group, cyclobutoxy group, cyclopentyloxy group or cyclohexyloxy group, more preferably cyclopropyloxy group or cyclobutoxy group. A hydrogen atom in the C3-C8 cycloalkoxy group is optionally replaced by the substituent C, if the substituent C is present.

The C2-C6 alkenyloxy group of the "C2-C6 alkenyloxy group optionally substituted with a substituent C" for R3 in formula (1) has the same definition as above, preferably a vinyloxy group, 1-propenyloxy group, allyloxy group, 1-butenyloxy group, 2-butenyloxy group or 3-butenyloxy group, more preferably vinyloxy group, 1-propenyloxy group or allyloxy group. When having a substituent C, a hydrogen atom in the C2-C6 alkenyloxy group is optionally replaced by the substituent C.

The “C2 to C6 haloalkenyloxy group” for R3 in formula (1) has the same meaning as defined above, preferably a 2-fluorovinyloxy group, a 2,2-difluorovinyloxy group, a 2,2- dichlorovinyloxy group, 3-fluoroallyloxy group, 3,3-difluoroallyloxy group or 3,3-dichloroallyloxy group, more preferably 2-fluorovinyloxy group or 2,2-difluoro It is a vinyloxy group.

The C3-C6 alkynyloxy group in the "C3-C6 alkynyloxy group optionally substituted with a substituent C" for R3 in formula (1) has the same definition as above, preferably a propargyloxy group. , 2-butynyloxy, or 3-butynyloxy, more preferably propargyloxy. When having a substituent C, a hydrogen atom in the C3-C6 alkynyloxy group is optionally replaced by the substituent C.

The “C3-C6 haloalkynyloxy group” for R3 in formula (1) has the same meaning as defined above, preferably 4,4-difluoro-2-butynyloxy group, 4-chloro-4,4-difluoro -2-butynyloxy group, 4-bromo-4,4-difluoro-2-butynyloxy group, or 4,4,4-trifluoro-2-butynyloxy group, more preferably 4,4-difluoro-2- butynyloxy group, or 4,4,4-trifluoro-2-butynyloxy group.

The aryl group of "an aryl group optionally substituted with a substituent D" for R3 in formula (1) has the same definition as above, and is preferably a phenyl group. A hydrogen in the aryl group is optionally replaced by the substituent D, if the substituent D is present.

The heteroaryl group of the "heteroaryl group optionally substituted with a substituent D" in R3 of formula (1) has the same meaning as defined above, preferably a pyridyl group, a pyrazinyl group, a thienyl group and a thiazolyl group. , an isothiazolyl group, a furyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a triazolyl group, an oxadiazolyl group, or a tetrazolyl group, more preferably a pyridyl group, an imidazolyl group, a pyrazolyl group, a triazolyl group, and a tetrazolyl group. be. A hydrogen in the heteroaryl group is optionally replaced by a substituent D, if a substituent D is present.

The aryloxy group of the "aryloxy group optionally substituted with a substituent D" in R3 of formula (1) has the same meaning as defined above, preferably a phenoxy group or a naphthyloxy group, and further A phenoxy group is preferred. A hydrogen atom in the aryloxy group is optionally replaced by a substituent D, if a substituent D is present.

The heteroaryloxy group of the "heteroaryloxy group optionally substituted with a substituent D" for R3 in formula (1) has the same meaning as defined above, preferably a pyridyloxy group, a pyridazinyloxy a pyrimidinyloxy group, a pyrazinyloxy group, a pyrazolyloxy group, a triazinyloxy group, a tetrazinyloxy group, a thienyloxy group, a thiazolyloxy group, an isothiazolyloxy group, or a thiadiazolyloxy group, more preferably a pyridyloxy group, a pyridazinyloxy group, a pyrimidinyloxy group, a pyrazinyloxy group, or a pyrazolyloxy group; A hydrogen atom in the heteroaryloxy group is optionally replaced by the substituent D, if the substituent D is present.

The aralkyloxy group of "an aralkyloxy group optionally substituted with a substituent D" in R3 of formula (1) has the same meaning as defined above, preferably a benzyloxy group, a phenethyloxy group, or a phenylpropyl It is an oxy group, more preferably a benzyloxy group or a phenethyloxy group. A hydrogen atom in the aralkyloxy group is optionally replaced by a substituent D, if a substituent D is present.

Ra and Rb of "RaRbN-" in R3 of formula (1) are the same as defined above. "RaRbN-" is preferably amino group, methylamino group, ethylamino group, (methoxymethyl)amino group, (2-methoxyethyl)amino group, (cyanomethyl)amino group, (2-cyanoethyl)amino group, dimethyl amino group, ethylmethylamino group, diethylamino group, (methoxymethyl)methylamino group, (2-methoxyethyl)methylamino group, (cyanomethyl)methylamino group, (2-cyanoethyl)methylamino group, 2,2-difluoro ethylamino group, 2,2,2-trifluoroethylamino group, cyclopropylamino group, (cyclopropyl)methylamino group, pyrrolidinyl group or piperidinyl group, more preferably amino group, dimethylamino group, ethyl A methylamino group or a diethylamino group.

Rc and L of "Rc-L-" in R3 of formula (1) are the same as defined above. "Rc-L-" is preferably a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, a trifluoromethanesulfinyl group, and a trifluoromethanesulfonyl group, more preferably a methylthio group and a methanesulfinyl group. , and a methanesulfonyl group.

Rx1 of "Rx1C(=O)-" in R3 of formula (1) has the same meaning as defined above. "Rx1C(=O)-" is preferably an acetyl group, a methoxyacetyl group, a cyanoacetyl group, a propionyl group, a difluoroacetyl group, a trifluoroacetyl group, a cyclopropanecarbonyl group, a methoxycarbonyl group, an ethoxycarbonyl group, 2 , 2-difluoroethoxycarbonyl group, 2,2,2-trifluoroethoxycarbonyl group, 3,3,3-trifluoropropyloxycarbonyl group, cyclopropyloxycarbonyl group, aminocarbonyl group, methylaminocarbonyl group, ethylamino carbonyl group, (methoxymethyl)aminocarbonyl group, (2-methoxyethyl)aminocarbonyl group, (cyanomethyl)aminocarbonyl group, (2-cyanoethyl)aminocarbonyl group, dimethylaminocarbonyl group, ethylmethylaminocarbonyl group, diethylaminocarbonyl group, (methoxymethyl)methylaminocarbonyl group, (2-methoxyethyl)methylaminocarbonyl group, (cyanomethyl)methylaminocarbonyl group, (2-cyanoethyl)methylaminocarbonyl group, 2,2-difluoroethylaminocarbonyl group, 2,2,2-trifluoroethylaminocarbonyl group, cyclopropylaminocarbonyl group, (cyclopropyl)methylaminocarbonyl group, pyrrolidinylcarbonyl group and piperidinylcarbonyl group, more preferably acetyl group, methoxyacetyl group, cyanoacetyl group, difluoroacetyl group, trifluoroacetyl group, methoxycarbonyl group, ethoxycarbonyl group, aminocarbonyl group, dimethylaminocarbonyl group, ethylmethylaminocarbonyl group, and diethylaminocarbonyl group.

Rx1 of "Rx1C(=O)O-" in R3 of formula (1) has the same definition as above. "Rx1C(=O)O-" is preferably an acetyloxy group, a methoxyacetyloxy group, a cyanoacetyloxy group, a propionyloxy group, a difluoroacetyloxy group, a trifluoroacetyloxy group, a cyclopropanecarbonyloxy group, a methoxy carbonyloxy group, ethoxycarbonyloxy group, 2,2-difluoroethoxycarbonyloxy group, 2,2,2-trifluoroethoxycarbonyloxy group, 3,3,3-trifluoropropyloxycarbonyloxy group, cyclopropyloxycarbonyl oxy group, aminocarbonyloxy group, methylaminocarbonyloxy group, ethylaminocarbonyloxy group, (methoxymethyl)aminocarbonyloxy group, (2-methoxyethyl)aminocarbonyloxy group, (cyanomethyl)aminocarbonyloxy group, (2 -Cyanoethyl) aminocarbonyloxy group, dimethylaminocarbonyloxy group, ethylmethylaminocarbonyloxy group, diethylaminocarbonyloxy group, (methoxymethyl) methylaminocarbonyloxy group, (2-methoxyethyl) methylaminocarbonyloxy group, (cyanomethyl ) methylaminocarbonyloxy group, (2-cyanoethyl)methylaminocarbonyloxy group, 2,2-difluoroethylaminocarbonyloxy group, 2,2,2-trifluoroethylaminocarbonyloxy group, cyclopropylaminocarbonyloxy group, (cyclopropyl)methylaminocarbonyloxy group, pyrrolidinylcarbonyloxy group and piperidinylcarbonyloxy group, more preferably acetyloxy group, methoxyacetyloxy group, cyanoacetyloxy group, difluoroacetyloxy group, a trifluoroacetyloxy group, a methoxycarbonyloxy group, an ethoxycarbonyloxy group, an aminocarbonyloxy group, a dimethylaminocarbonyloxy group, an ethylmethylaminocarbonyloxy group, and a diethylaminocarbonyloxy group;

"Rx2C(=O)N(Rx3)-" in R3 of formula (1) (here, Rx2 is a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 A haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or RaRbN— (wherein Ra and Rb are ), and Rx3 represents a hydrogen atom, a C1 to C6 alkyl group optionally substituted with a substituent B, a C1 to C6 haloalkyl group, or a C3 to C8 cycloalkyl group.) The terms are synonymous with the definitions given above. Regarding the "C1-C6 alkyl group optionally substituted with a substituent B", when the substituent B is present, the hydrogen atom in the C1-C6 alkyl group is optionally substituted with the substituent B. .

Rx2 is preferably a hydrogen atom, a methyl group, a methoxymethyl group, a cyanomethyl group, an ethyl group, a difluoromethyl group, a trifluoromethyl group, a cyclopropyl group, a methoxy group, an ethoxy group, 2,2-difluoroethoxy, 2, 2,2-trifluoroethoxy group, cyclopropyloxy group, amino group, methylamino group, ethylamino group, (methoxymethyl) amino group, (2-methoxyethyl) amino group, (cyanomethyl) amino group, (2- cyanoethyl)amino group, dimethylamino group, ethylmethylamino group, diethylamino group, (methoxymethyl)methylamino group, (2-methoxyethyl)methylamino group, (cyanomethyl)methylamino group, (2-cyanoethyl)methylamino group , 2,2-difluoroethylamino group, 2,2,2-trifluoroethylamino group, cyclopropylamino group, (cyclopropyl)methylamino group, pyrrolidinyl group or piperidinyl group, more preferably a hydrogen atom , methyl group, methoxymethyl group, cyanomethyl group, difluoromethyl group, trifluoromethyl group, methoxy group, ethoxy group, amino group, dimethylamino group, ethylmethylamino group or diethylamino group. Rx3 is preferably a hydrogen atom, a methyl group, a methoxymethyl group, an ethoxymethyl group, a cyanomethyl group, an ethyl group, a 2-methoxyethyl group, a 2-ethoxyethyl group, a 2-cyanoethyl group, a propyl group, 2, a 2-difluoroethyl group, a 2,2,2-trifluoroethyl group, or a cyclopropyl group, more preferably a hydrogen atom, a methyl group, a methoxymethyl group, a cyanomethyl group, an ethyl group, a 2-methoxyethyl group, 2,2-difluoroethyl group or 2,2,2-trifluoroethyl group.

"Rx4Rx5C=NO-" for R3 in formula (1) (where Rx4 and Rx5 are each independently a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group, or RaRbN- (wherein Ra and Rb are ) has the same meaning as defined above. Regarding the "C1-C6 alkyl group optionally substituted with a substituent B", when the substituent B is present, the hydrogen atom in the C1-C6 alkyl group is optionally substituted with the substituent B. .

Rx4 and Rx5 are preferably methyl group, ethyl group, propyl group, isopropyl group, trifluoromethyl group, 2,2,2-trifluoroethyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group, methoxy group and ethoxy group , isopropyloxy group, difluoromethoxy group, trifluoromethoxy group, 2,2-difluoroethoxy group, 2,2,2-trifluoroethoxy group, cyclopropyloxy group, cyclobutyloxy group, cyclopentyloxy group, amino group, methylamino group, ethylamino group, (methoxymethyl)amino group, (2-methoxyethyl)amino group, (cyanomethyl)amino group, (2-cyanoethyl)amino group, dimethylamino group, ethylmethylamino group, diethylamino group, (Methoxymethyl)methylamino group, (2-methoxyethyl)methylamino group, (cyanomethyl)methylamino group, (2-cyanoethyl)methylamino group, 2,2-difluoroethylamino group, 2,2,2-tri fluoroethylamino group, cyclopropylamino group, (cyclopropyl)methylamino group, pyrrolidinyl group or piperidinyl group, more preferably methyl group, ethyl group, trifluoromethyl group, 2,2,2-trifluoro ethyl group, methoxy group, ethoxy group, 2,2,2-trifluoroethoxy group, dimethylamino group, ethylmethylamino group or diethylamino group.

The "3- to 6-membered ring group containing 1 to 2 oxygen atoms" for R3 in formula (1) has the same meaning as defined above, preferably an oxolanyl group, an oxanyl group, or a 1,3-dioxolanyl group. , or a 1,3-dioxanyl group, more preferably a 1,3-dioxolanyl group or a 1,3-dioxanyl group.

Y in Formula (1) represents a phenyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, a tetrazinyl group, a thienyl group, a thiazolyl group, an isothiazolyl group, or a thiadiazolyl group. Among them, a phenyl group or a pyridyl group is preferred, and a phenyl group is particularly preferred.
The phenyl group is substituted with R4 at the ortho position and optionally with 0 to 4 R5 (provided that when there are two or more R5 substituted, each R5 represents an independent substituent).
The pyridyl group, the pyridazinyl group, the pyrimidinyl group, the pyrazinyl group, the triazinyl group, or the tetrazinyl group is substituted with R4 at the ortho position, and further substituted with 0 to 3 R5 as appropriate (provided that 2 or more When R5 is present, each R5 represents an independent substituent.).
In the thienyl group, the thiazolyl group, the isothiazolyl group, or the thiadiazolyl group, R4 is substituted at the ortho position, and R5 is optionally substituted with 0 to 2 substituents (provided that when there are two or more R5 substituted, R5 is represents an independent substituent).
When there are two or more substituted R5 in Y of formula (1), each R5 represents an independent substituent, which may be the same or different, and is not particularly limited.

R4 in formula (1) is a hydroxyl group, a cyano group, a nitro group, a halogen atom, a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group optionally substituted with a substituent C a C3-C8 cycloalkyl group optionally substituted with a substituent C, a C2-C6 alkenyl group optionally substituted with a substituent C, a C2-C6 haloalkenyl group, a C2-C6 alkynyl optionally substituted with a substituent C a C2-C6 haloalkynyl group, a C1-C6 alkoxy group optionally substituted with a substituent C, a C1-C6 haloalkoxy group, a C3-C8 cyclo optionally substituted with a substituent C alkoxy group, C2-C6 alkenyloxy group optionally substituted with substituent C, C2-C6 haloalkenyloxy group, C3-C6 alkynyloxy group optionally substituted with substituent C, C3- haloalkynyloxy group of C6, an aryl group optionally substituted with a substituent D, a heteroaryl group optionally substituted with a substituent D, an aralkyloxy group optionally substituted with a substituent D, RaRbN- (where Ra and Rb are as defined above), Rc-L- (wherein Rc and L are as defined above), Rx1C (=O)- (where Rx1 is as defined above.), Rx1C(=O)O- (wherein Rx1 is as defined above.), Rx2C(=O)N(Rx3)- (wherein Rx2 is a hydrogen atom, substituted C1-C6 alkyl group optionally substituted by group B, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C3-C8 represents a cycloalkoxy group or RaRbN- (wherein Ra and Rb are as defined above), Rx3 is a hydrogen atom, a C1 to C6 alkyl group optionally substituted with a substituent B, C1 ~C6 haloalkyl group, or C3-C8 cycloalkyl group. a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or RaRbN - (wherein Ra and Rb are as defined above)), or a 3- to 6-membered ring group containing 1 to 2 oxygen atoms.

Among them, R4 is a halogen atom, a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group, a C1-C6 alkoxy group optionally substituted with a substituent C, or A C1-C6 haloalkoxy group is preferred, and a halogen atom, a C1-C6 alkyl group optionally substituted with a substituent C, or a C1-C6 alkoxy group optionally substituted with a substituent C A halogen atom is preferred, and a halogen atom is particularly preferred.

R4 in formula (1) includes a hydroxyl group, a cyano group and a nitro group.

The halogen atom for R4 in formula (1) has the same definition as above, preferably a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, particularly preferably a fluorine atom.

The C1-C6 alkyl group of the "C1-C6 alkyl group optionally substituted with a substituent C" for R4 in formula (1) has the same definition as above, and is preferably a methyl group or an ethyl group. , propyl group or isopropyl group, more preferably methyl group or ethyl group. When having a substituent C, a hydrogen atom in the C1-C6 alkyl group is optionally replaced by the substituent C.

The “C1-C6 haloalkyl group” for R4 in formula (1) has the same meaning as defined above, preferably difluoromethyl group, trifluoromethyl group, 2,2-difluoroethyl group, 2,2,2 -trifluoroethyl group, 3,3-difluoropropyl group, or 3,3,3-trifluoropropyl group, more preferably difluoromethyl group, trifluoromethyl group, 2,2-difluoroethyl group, or It is a 2,2,2-trifluoroethyl group.

The C3-C8 cycloalkyl group of the "C3-C8 cycloalkyl group optionally substituted with a substituent C" for R4 in formula (1) has the same definition as above, preferably a cyclopropyl group. , cyclobutyl group, cyclopentyl group or cyclohexyl group, more preferably cyclopropyl group or cyclobutyl group. A hydrogen atom in the C3-C8 cycloalkyl group is optionally replaced by a substituent C, if it has a substituent C.

The C2-C6 alkenyl group of the "C2-C6 alkenyl group optionally substituted with a substituent C" for R4 in formula (1) has the same definition as above, preferably a vinyl group, 1- It is a propenyl group, allyl group, 1-butenyl group, 2-butenyl group or 3-butenyl group, more preferably vinyl group, 1-propenyl group or allyl group. If a substituent C is present, a hydrogen atom in the C2-C6 alkenyl group is optionally replaced by the substituent C.

The “C2-C6 haloalkenyl group” for R4 in formula (1) has the same meaning as defined above, and is preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, or a 2,2-dichlorovinyl group. , 3-fluoroallyl group, 3,3-difluoroallyl group or 3,3-dichloroallyl group, more preferably 2-fluorovinyl group or 2,2-difluorovinyl group.

The C2-C6 alkynyl group of the "C2-C6 alkynyl group optionally substituted with a substituent C" for R4 in formula (1) has the same meaning as defined above, preferably an ethynyl group, 1- It is a propynyl group, propargyl group, 1-butynyl group, 2-butynyl group or 3-butynyl group, more preferably an ethynyl group or propargyl group. When having a substituent C, a hydrogen atom in the C2-C6 alkynyl group is optionally replaced by the substituent C.

The “C2-C6 haloalkynyl group” for R4 in formula (1) has the same meaning as defined above, preferably 3,3-difluoro-1-propynyl group, 3,3,3-trifluoro-1 -propynyl group, 4,4-difluoro-1-butynyl group, 4,4-difluoro-2-butynyl group, 4,4,4-trifluoro-1-butynyl group, or 4,4,4-trifluoro- It is a 2-butynyl group, more preferably a 3,3-difluoro-1-propynyl group or a 3,3,3-trifluoro-1-propynyl group.

The C1-C6 alkoxy group of the "C1-C6 alkoxy group optionally substituted with a substituent C" in R4 of formula (1) has the same definition as above, preferably a methoxy group or an ethoxy group. , propyloxy, isopropyloxy, butoxy or isobutoxy, more preferably methoxy, ethoxy, propyloxy or isopropyloxy. When having a substituent C, a hydrogen atom in the C1-C6 alkoxy group is optionally replaced by the substituent C.

The “C1-C6 haloalkoxy group” for R4 in formula (1) has the same meaning as defined above, preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, 2,2, 2-trifluoroethoxy group, 3,3-difluoropropyloxy group or 3,3,3-trifluoropropyloxy group, more preferably difluoromethoxy group, trifluoromethoxy group and 2,2-difluoroethoxy or a 2,2,2-trifluoroethoxy group.

The C3-C8 cycloalkoxy group of the "C3-C8 cycloalkoxy group optionally substituted with a substituent C" for R4 in formula (1) has the same definition as above, preferably cyclopropyloxy group, cyclobutoxy group, cyclopentyloxy group or cyclohexyloxy group, more preferably cyclopropyloxy group or cyclobutoxy group. A hydrogen atom in the C3-C8 cycloalkoxy group is optionally replaced by the substituent C, if the substituent C is present.

The C2-C6 alkenyloxy group in the "C2-C6 alkenyloxy group optionally substituted with a substituent C" for R4 in formula (1) has the same definition as above, preferably a vinyloxy group, 1-propenyloxy group, allyloxy group, 1-butenyloxy group, 2-butenyloxy group or 3-butenyloxy group, more preferably vinyloxy group, 1-propenyloxy group or allyloxy group. When having a substituent C, a hydrogen atom in the C2-C6 alkenyloxy group is optionally replaced by the substituent C.

The “C2 to C6 haloalkenyloxy group” for R4 in formula (1) has the same meaning as defined above, preferably a 2-fluorovinyloxy group, a 2,2-difluorovinyloxy group, a 2,2- dichlorovinyloxy group, 3-fluoroallyloxy group, 3,3-difluoroallyloxy group or 3,3-dichloroallyloxy group, more preferably 2-fluorovinyloxy group or 2,2-difluoro It is a vinyloxy group.

The C3-C6 alkynyloxy group in the "C3-C6 alkynyloxy group optionally substituted with a substituent C" for R4 in formula (1) has the same definition as above, preferably a propargyloxy group. , 2-butynyloxy, or 3-butynyloxy, more preferably propargyloxy. When having a substituent C, a hydrogen atom in the C3-C6 alkynyloxy group is optionally replaced by the substituent C.

The “C3-C6 haloalkynyloxy group” for R4 in formula (1) has the same meaning as defined above, preferably 4,4-difluoro-2-butynyloxy group, 4-chloro-4,4-difluoro -2-butynyloxy group, 4-bromo-4,4-difluoro-2-butynyloxy group, or 4,4,4-trifluoro-2-butynyloxy group, more preferably 4,4-difluoro-2- butynyloxy group, or 4,4,4-trifluoro-2-butynyloxy group.

The aryl group of "an aryl group optionally substituted with a substituent D" for R4 in formula (1) has the same definition as above, and is preferably a phenyl group. A hydrogen in the aryl group is optionally replaced by the substituent D, if the substituent D is present.

The heteroaryl group of the "heteroaryl group optionally substituted with a substituent D" in R4 of formula (1) has the same meaning as defined above, and is preferably a pyridyl group, a pyrazinyl group, a thienyl group or a thiazolyl group. , an isothiazolyl group, a furyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a triazolyl group, an oxadiazolyl group, or a tetrazolyl group, more preferably a pyridyl group, an imidazolyl group, a pyrazolyl group, a triazolyl group, and a tetrazolyl group. be. A hydrogen in the heteroaryl group is optionally replaced by a substituent D, if a substituent D is present.

The aralkyloxy group of "an aralkyloxy group optionally substituted with a substituent D" in R4 of formula (1) has the same meaning as defined above, preferably a benzyloxy group, a phenethyloxy group, or a phenylpropyl It is an oxy group, more preferably a benzyloxy group or a phenethyloxy group. A hydrogen atom in the aralkyloxy group is optionally replaced by a substituent D, if a substituent D is present.

Ra and Rb of "RaRbN-" in R4 of formula (1) are the same as defined above. "RaRbN-" is preferably amino group, methylamino group, ethylamino group, (methoxymethyl)amino group, (2-methoxyethyl)amino group, (cyanomethyl)amino group, (2-cyanoethyl)amino group, dimethyl amino group, ethylmethylamino group, diethylamino group, (methoxymethyl)methylamino group, (2-methoxyethyl)methylamino group, (cyanomethyl)methylamino group, (2-cyanoethyl)methylamino group, 2,2-difluoro ethylamino group, 2,2,2-trifluoroethylamino group, cyclopropylamino group, (cyclopropyl)methylamino group, pyrrolidinyl group or piperidinyl group, more preferably amino group, dimethylamino group, ethyl A methylamino group or a diethylamino group.

Rc and L of "Rc-L-" in R4 of formula (1) are the same as defined above. "Rc-L-" is preferably a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, a trifluoromethanesulfinyl group, and a trifluoromethanesulfonyl group, more preferably a methylthio group and a methanesulfinyl group. , and a methanesulfonyl group.

Rx1 of "Rx1C(=O)-" in R4 of formula (1) has the same meaning as defined above. "Rx1C(=O)-" is preferably an acetyl group, a methoxyacetyl group, a cyanoacetyl group, a propionyl group, a difluoroacetyl group, a trifluoroacetyl group, a cyclopropanecarbonyl group, a methoxycarbonyl group, an ethoxycarbonyl group, 2 , 2-difluoroethoxycarbonyl group, 2,2,2-trifluoroethoxycarbonyl group, 3,3,3-trifluoropropyloxycarbonyl group, cyclopropyloxycarbonyl group, aminocarbonyl group, methylaminocarbonyl group, ethylamino carbonyl group, (methoxymethyl)aminocarbonyl group, (2-methoxyethyl)aminocarbonyl group, (cyanomethyl)aminocarbonyl group, (2-cyanoethyl)aminocarbonyl group, dimethylaminocarbonyl group, ethylmethylaminocarbonyl group, diethylaminocarbonyl group, (methoxymethyl)methylaminocarbonyl group, (2-methoxyethyl)methylaminocarbonyl group, (cyanomethyl)methylaminocarbonyl group, (2-cyanoethyl)methylaminocarbonyl group, 2,2-difluoroethylaminocarbonyl group, 2,2,2-trifluoroethylaminocarbonyl group, cyclopropylaminocarbonyl group, (cyclopropyl)methylaminocarbonyl group, pyrrolidinylcarbonyl group and piperidinylcarbonyl group, more preferably acetyl group, methoxyacetyl group, cyanoacetyl group, difluoroacetyl group, trifluoroacetyl group, methoxycarbonyl group, ethoxycarbonyl group, aminocarbonyl group, dimethylaminocarbonyl group, ethylmethylaminocarbonyl group, and diethylaminocarbonyl group.

Rx1 of "Rx1C(=O)O-" in R4 of formula (1) has the same meaning as defined above. "Rx1C(=O)O-" is preferably an acetyloxy group, a methoxyacetyloxy group, a cyanoacetyloxy group, a propionyloxy group, a difluoroacetyloxy group, a trifluoroacetyloxy group, a cyclopropanecarbonyloxy group, a methoxy carbonyloxy group, ethoxycarbonyloxy group, 2,2-difluoroethoxycarbonyloxy group, 2,2,2-trifluoroethoxycarbonyloxy group, 3,3,3-trifluoropropyloxycarbonyloxy group, cyclopropyloxycarbonyl oxy group, aminocarbonyloxy group, methylaminocarbonyloxy group, ethylaminocarbonyloxy group, (methoxymethyl)aminocarbonyloxy group, (2-methoxyethyl)aminocarbonyloxy group, (cyanomethyl)aminocarbonyloxy group, (2 -Cyanoethyl) aminocarbonyloxy group, dimethylaminocarbonyloxy group, ethylmethylaminocarbonyloxy group, diethylaminocarbonyloxy group, (methoxymethyl) methylaminocarbonyloxy group, (2-methoxyethyl) methylaminocarbonyloxy group, (cyanomethyl ) methylaminocarbonyloxy group, (2-cyanoethyl)methylaminocarbonyloxy group, 2,2-difluoroethylaminocarbonyloxy group, 2,2,2-trifluoroethylaminocarbonyloxy group, cyclopropylaminocarbonyloxy group, (cyclopropyl)methylaminocarbonyloxy group, pyrrolidinylcarbonyloxy group and piperidinylcarbonyloxy group, more preferably acetyloxy group, methoxyacetyloxy group, cyanoacetyloxy group, difluoroacetyloxy group, a trifluoroacetyloxy group, a methoxycarbonyloxy group, an ethoxycarbonyloxy group, an aminocarbonyloxy group, a dimethylaminocarbonyloxy group, an ethylmethylaminocarbonyloxy group, and a diethylaminocarbonyloxy group;

"Rx2C(=O)N(Rx3)-" in R4 of formula (1) (where Rx2 is a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 A haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or RaRbN— (wherein Ra and Rb are ), and Rx3 represents a hydrogen atom, a C1 to C6 alkyl group optionally substituted with a substituent B, a C1 to C6 haloalkyl group, or a C3 to C8 cycloalkyl group.) The terms are synonymous with the definitions given above. Regarding the "C1-C6 alkyl group optionally substituted with a substituent B", when the substituent B is present, the hydrogen atom in the C1-C6 alkyl group is optionally substituted with the substituent B. .

Rx2 is preferably a hydrogen atom, a methyl group, a methoxymethyl group, a cyanomethyl group, an ethyl group, a difluoromethyl group, a trifluoromethyl group, a cyclopropyl group, a methoxy group, an ethoxy group, 2,2-difluoroethoxy, 2, 2,2-trifluoroethoxy group, cyclopropyloxy group, amino group, methylamino group, ethylamino group, (methoxymethyl) amino group, (2-methoxyethyl) amino group, (cyanomethyl) amino group, (2- cyanoethyl)amino group, dimethylamino group, ethylmethylamino group, diethylamino group, (methoxymethyl)methylamino group, (2-methoxyethyl)methylamino group, (cyanomethyl)methylamino group, (2-cyanoethyl)methylamino group , 2,2-difluoroethylamino group, 2,2,2-trifluoroethylamino group, cyclopropylamino group, (cyclopropyl)methylamino group, pyrrolidinyl group or piperidinyl group, more preferably a hydrogen atom , methyl group, methoxymethyl group, cyanomethyl group, difluoromethyl group, trifluoromethyl group, methoxy group, ethoxy group, amino group, dimethylamino group, ethylmethylamino group or diethylamino group. Rx3 is preferably a hydrogen atom, a methyl group, a methoxymethyl group, an ethoxymethyl group, a cyanomethyl group, an ethyl group, a 2-methoxyethyl group, a 2-ethoxyethyl group, a 2-cyanoethyl group, a propyl group, 2, a 2-difluoroethyl group, a 2,2,2-trifluoroethyl group, or a cyclopropyl group, more preferably a hydrogen atom, a methyl group, a methoxymethyl group, a cyanomethyl group, an ethyl group, a 2-methoxyethyl group, 2,2-difluoroethyl group or 2,2,2-trifluoroethyl group.

"Rx4Rx5C=NO-" for R4 in formula (1) (where Rx4 and Rx5 are each independently a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group, or RaRbN- (wherein Ra and Rb are ) has the same meaning as defined above. Regarding the "C1-C6 alkyl group optionally substituted with a substituent B", when the substituent B is present, the hydrogen atom in the C1-C6 alkyl group is optionally substituted with the substituent B. .

Rx4 and Rx5 are preferably methyl group, ethyl group, propyl group, isopropyl group, trifluoromethyl group, 2,2,2-trifluoroethyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group, methoxy group and ethoxy group , isopropyloxy group, difluoromethoxy group, trifluoromethoxy group, 2,2-difluoroethoxy group, 2,2,2-trifluoroethoxy group, cyclopropyloxy group, cyclobutyloxy group, cyclopentyloxy group, amino group, methylamino group, ethylamino group, (methoxymethyl)amino group, (2-methoxyethyl)amino group, (cyanomethyl)amino group, (2-cyanoethyl)amino group, dimethylamino group, ethylmethylamino group, diethylamino group, (Methoxymethyl)methylamino group, (2-methoxyethyl)methylamino group, (cyanomethyl)methylamino group, (2-cyanoethyl)methylamino group, 2,2-difluoroethylamino group, 2,2,2-tri fluoroethylamino group, cyclopropylamino group, (cyclopropyl)methylamino group, pyrrolidinyl group or piperidinyl group, more preferably methyl group, ethyl group, trifluoromethyl group, 2,2,2-trifluoro ethyl group, methoxy group, ethoxy group, 2,2,2-trifluoroethoxy group, dimethylamino group, ethylmethylamino group or diethylamino group.

The "3- to 6-membered ring group containing 1 to 2 oxygen atoms" for R4 in formula (1) has the same meaning as defined above, and is preferably an oxolanyl group, an oxanyl group, or a 1,3-dioxolanyl group. , or a 1,3-dioxanyl group, more preferably a 1,3-dioxolanyl group or a 1,3-dioxanyl group.

R5 in formula (1) has the same definition as R4 described above. That is, a hydroxyl group, a cyano group, a nitro group, a halogen atom, a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group optionally substituted with a substituent C, a C3-C8 optionally substituted with a substituent C cycloalkyl group, C2 to C6 alkenyl group optionally substituted by substituent C, C2 to C6 haloalkenyl group, C2 to C6 alkynyl group optionally substituted by substituent C, C2 to C6 haloalkynyl group, C1-C6 alkoxy group optionally substituted with substituent C, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group optionally substituted with substituent C, substituent C C2-C6 alkenyloxy group optionally substituted with C2-C6 haloalkenyloxy group, C3-C6 alkynyloxy group optionally substituted with substituent C, C3-C6 haloalkynyloxy group , an aryl group optionally substituted with a substituent D, a heteroaryl group optionally substituted with a substituent D, an aralkyloxy group optionally substituted with a substituent D, RaRbN- (wherein Ra and Rb is as defined above.), Rc-L- (wherein Rc and L are as defined above), Rx1C(=O)- (wherein Rx1 is as defined above. ), Rx1C (=O) O- (where Rx1 has the same definition as above), Rx2C (=O) N (Rx3)- (where Rx2 is a hydrogen atom, optionally substituted with a substituent B a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or RaRbN - (Here, Ra and Rb are as defined above.), Rx3 is a hydrogen atom, a C1 to C6 alkyl group optionally substituted with a substituent B, a C1 to C6 haloalkyl group, or represents a C3-C8 cycloalkyl group), Rx4Rx5C=NO- (where Rx4 and Rx5 are each independently a hydrogen atom, C1-C6 optionally substituted with a substituent B) alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group, or RaRbN- (where Ra and Rb are as defined above.), or a 3- to 6-membered ring group containing 1 to 2 oxygen atoms.

Among them, R5 is a hydroxyl group, a cyano group, a halogen atom, a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group optionally substituted with a substituent C, a C3-C8 optionally substituted with a substituent C a cycloalkyl group, a C2 to C6 alkenyl group optionally substituted with a substituent C, a C2 to C6 alkynyl group optionally substituted with a substituent C, a C1 optionally substituted with a substituent C to C6 alkoxy group, C1 to C6 haloalkoxy group, C3 to C8 cycloalkoxy group optionally substituted by substituent C, C2 to C6 alkenyloxy group optionally substituted by substituent C, a C3-C6 alkynyloxy group optionally substituted with a substituent C, a heteroaryl group optionally substituted with a substituent D, Rc-L- (wherein Rc is a C1-C6 alkyl group, or represents a C1 _- C6 haloalkyl group, and L represents S, SO, or SO2. , a cyano group, a halogen atom, a C1-C6 alkoxy group optionally substituted with a substituent C, or a C1-C6 haloalkoxy group are preferable.

R5 in formula (1) includes a hydroxyl group, a cyano group, and a nitro group.

The halogen atom for R5 in formula (1) has the same definition as above, preferably a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, particularly preferably a fluorine atom.

The C1-C6 alkyl group of the "C1-C6 alkyl group optionally substituted with a substituent C" for R5 in formula (1) has the same definition as above, and is preferably a methyl group or an ethyl group. , propyl group or isopropyl group, more preferably methyl group or ethyl group. When having a substituent C, a hydrogen atom in the C1-C6 alkyl group is optionally replaced by the substituent C.

The “C1-C6 haloalkyl group” for R5 in formula (1) has the same meaning as defined above, preferably difluoromethyl group, trifluoromethyl group, 2,2-difluoroethyl group, 2,2,2 -trifluoroethyl group, 3,3-difluoropropyl group, or 3,3,3-trifluoropropyl group, more preferably difluoromethyl group, trifluoromethyl group, 2,2-difluoroethyl group, or It is a 2,2,2-trifluoroethyl group.

The C3-C8 cycloalkyl group of the "C3-C8 cycloalkyl group optionally substituted with a substituent C" for R5 in formula (1) is as defined above, preferably a cyclopropyl group , cyclobutyl group, cyclopentyl group or cyclohexyl group, more preferably cyclopropyl group or cyclobutyl group. A hydrogen atom in the C3-C8 cycloalkyl group is optionally replaced by a substituent C, if it has a substituent C.

The C2-C6 alkenyl group of the "C2-C6 alkenyl group optionally substituted with a substituent C" for R5 in formula (1) has the same definition as above, preferably a vinyl group, 1- It is a propenyl group, allyl group, 1-butenyl group, 2-butenyl group or 3-butenyl group, more preferably vinyl group, 1-propenyl group or allyl group. If a substituent C is present, a hydrogen atom in the C2-C6 alkenyl group is optionally replaced by the substituent C.

The “C2-C6 haloalkenyl group” for R5 in formula (1) has the same meaning as defined above, and is preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, or a 2,2-dichlorovinyl group. , 3-fluoroallyl group, 3,3-difluoroallyl group or 3,3-dichloroallyl group, more preferably 2-fluorovinyl group or 2,2-difluorovinyl group.

The C2-C6 alkynyl group of the "C2-C6 alkynyl group optionally substituted with a substituent C" for R5 in formula (1) has the same meaning as defined above, preferably an ethynyl group, 1- It is a propynyl group, propargyl group, 1-butynyl group, 2-butynyl group or 3-butynyl group, more preferably an ethynyl group or propargyl group. When having a substituent C, a hydrogen atom in the C2-C6 alkynyl group is optionally replaced by the substituent C.

The “C2-C6 haloalkynyl group” for R5 in formula (1) has the same meaning as defined above, preferably 3,3-difluoro-1-propynyl group, 3,3,3-trifluoro-1 -propynyl group, 4,4-difluoro-1-butynyl group, 4,4-difluoro-2-butynyl group, 4,4,4-trifluoro-1-butynyl group, or 4,4,4-trifluoro- It is a 2-butynyl group, more preferably a 3,3-difluoro-1-propynyl group or a 3,3,3-trifluoro-1-propynyl group.

The C1-C6 alkoxy group of the "C1-C6 alkoxy group optionally substituted with a substituent C" for R5 in formula (1) has the same definition as above, preferably a methoxy group or an ethoxy group. , propyloxy, isopropyloxy, butoxy or isobutoxy, more preferably methoxy, ethoxy, propyloxy or isopropyloxy, particularly preferably methoxy. When having a substituent C, a hydrogen atom in the C1-C6 alkoxy group is optionally replaced by the substituent C.

The “C1-C6 haloalkoxy group” for R5 in formula (1) has the same meaning as defined above, preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, 2,2, 2-trifluoroethoxy group, 3,3-difluoropropyloxy group or 3,3,3-trifluoropropyloxy group, more preferably difluoromethoxy group, trifluoromethoxy group and 2,2-difluoroethoxy or a 2,2,2-trifluoroethoxy group, particularly preferably a 2,2,2-trifluoroethoxy group.

The C3-C8 cycloalkoxy group in the "C3-C8 cycloalkoxy group optionally substituted with a substituent C" for R5 in formula (1) has the same definition as above, preferably cyclopropyloxy group, cyclobutoxy group, cyclopentyloxy group or cyclohexyloxy group, more preferably cyclopropyloxy group or cyclobutoxy group. A hydrogen atom in the C3-C8 cycloalkoxy group is optionally replaced by the substituent C, if the substituent C is present.

The C2-C6 alkenyloxy group in the "C2-C6 alkenyloxy group optionally substituted with a substituent C" for R5 in formula (1) has the same meaning as defined above, preferably a vinyloxy group, 1-propenyloxy group, allyloxy group, 1-butenyloxy group, 2-butenyloxy group or 3-butenyloxy group, more preferably vinyloxy group, 1-propenyloxy group or allyloxy group. When having a substituent C, a hydrogen atom in the C2-C6 alkenyloxy group is optionally replaced by the substituent C.

The "C2-C6 haloalkenyloxy group" for R5 in formula (1) has the same meaning as defined above, preferably a 2-fluorovinyloxy group, a 2,2-difluorovinyloxy group, a 2,2- dichlorovinyloxy group, 3-fluoroallyloxy group, 3,3-difluoroallyloxy group or 3,3-dichloroallyloxy group, more preferably 2-fluorovinyloxy group or 2,2-difluoro It is a vinyloxy group.

The C3-C6 alkynyloxy group in the "C3-C6 alkynyloxy group optionally substituted with a substituent C" for R5 in formula (1) has the same definition as above, preferably a propargyloxy group. , 2-butynyloxy, or 3-butynyloxy, more preferably propargyloxy. When having a substituent C, a hydrogen atom in the C3-C6 alkynyloxy group is optionally replaced by the substituent C.

The “C3-C6 haloalkynyloxy group” for R5 in formula (1) has the same meaning as defined above, preferably 4,4-difluoro-2-butynyloxy group, 4-chloro-4,4-difluoro -2-butynyloxy group, 4-bromo-4,4-difluoro-2-butynyloxy group, or 4,4,4-trifluoro-2-butynyloxy group, more preferably 4,4-difluoro-2- butynyloxy group, or 4,4,4-trifluoro-2-butynyloxy group.

The aryl group of "an aryl group optionally substituted with a substituent D" for R5 in formula (1) has the same definition as above, and is preferably a phenyl group. A hydrogen in the aryl group is optionally replaced by the substituent D, if the substituent D is present.

The heteroaryl group of the "heteroaryl group optionally substituted with a substituent D" for R5 in formula (1) has the same meaning as defined above, preferably a pyridyl group, a pyrazinyl group, a thienyl group and a thiazolyl group. , an isothiazolyl group, a furyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a triazolyl group, an oxadiazolyl group, or a tetrazolyl group, more preferably a pyridyl group, an imidazolyl group, a pyrazolyl group, a triazolyl group, and a tetrazolyl group. be. A hydrogen in the heteroaryl group is optionally replaced by a substituent D, if a substituent D is present.

The aralkyloxy group of "an aralkyloxy group optionally substituted with a substituent D" in R5 of formula (1) has the same meaning as defined above, preferably a benzyloxy group, a phenethyloxy group, or a phenylpropyl It is an oxy group, more preferably a benzyloxy group or a phenethyloxy group. A hydrogen atom in the aralkyloxy group is optionally replaced by a substituent D, if a substituent D is present.

Ra and Rb of "RaRbN-" in R5 of formula (1) are the same as defined above. "RaRbN-" is preferably amino group, methylamino group, ethylamino group, (methoxymethyl)amino group, (2-methoxyethyl)amino group, (cyanomethyl)amino group, (2-cyanoethyl)amino group, dimethyl amino group, ethylmethylamino group, diethylamino group, (methoxymethyl)methylamino group, (2-methoxyethyl)methylamino group, (cyanomethyl)methylamino group, (2-cyanoethyl)methylamino group, 2,2-difluoro ethylamino group, 2,2,2-trifluoroethylamino group, cyclopropylamino group, (cyclopropyl)methylamino group, pyrrolidinyl group or piperidinyl group, more preferably amino group, dimethylamino group, ethyl A methylamino group or a diethylamino group.

Rc and L of "Rc-L-" in R5 of formula (1) are the same as defined above. "Rc-L-" is preferably a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, a trifluoromethanesulfinyl group, and a trifluoromethanesulfonyl group, more preferably a methylthio group and a methanesulfinyl group. , and a methanesulfonyl group.

Rx1 of "Rx1C(=O)-" in R5 of formula (1) has the same meaning as defined above. "Rx1C(=O)-" is preferably an acetyl group, a methoxyacetyl group, a cyanoacetyl group, a propionyl group, a difluoroacetyl group, a trifluoroacetyl group, a cyclopropanecarbonyl group, a methoxycarbonyl group, an ethoxycarbonyl group, 2 , 2-difluoroethoxycarbonyl group, 2,2,2-trifluoroethoxycarbonyl group, 3,3,3-trifluoropropyloxycarbonyl group, cyclopropyloxycarbonyl group, aminocarbonyl group, methylaminocarbonyl group, ethylamino carbonyl group, (methoxymethyl)aminocarbonyl group, (2-methoxyethyl)aminocarbonyl group, (cyanomethyl)aminocarbonyl group, (2-cyanoethyl)aminocarbonyl group, dimethylaminocarbonyl group, ethylmethylaminocarbonyl group, diethylaminocarbonyl group, (methoxymethyl)methylaminocarbonyl group, (2-methoxyethyl)methylaminocarbonyl group, (cyanomethyl)methylaminocarbonyl group, (2-cyanoethyl)methylaminocarbonyl group, 2,2-difluoroethylaminocarbonyl group, 2,2,2-trifluoroethylaminocarbonyl group, cyclopropylaminocarbonyl group, (cyclopropyl)methylaminocarbonyl group, pyrrolidinylcarbonyl group and piperidinylcarbonyl group, more preferably acetyl group, methoxyacetyl group, cyanoacetyl group, difluoroacetyl group, trifluoroacetyl group, methoxycarbonyl group, ethoxycarbonyl group, aminocarbonyl group, dimethylaminocarbonyl group, ethylmethylaminocarbonyl group, and diethylaminocarbonyl group.

Rx1 of "Rx1C(=O)O-" in R5 of formula (1) has the same meaning as defined above. "Rx1C(=O)O-" is preferably an acetyloxy group, a methoxyacetyloxy group, a cyanoacetyloxy group, a propionyloxy group, a difluoroacetyloxy group, a trifluoroacetyloxy group, a cyclopropanecarbonyloxy group, a methoxy carbonyloxy group, ethoxycarbonyloxy group, 2,2-difluoroethoxycarbonyloxy group, 2,2,2-trifluoroethoxycarbonyloxy group, 3,3,3-trifluoropropyloxycarbonyloxy group, cyclopropyloxycarbonyl oxy group, aminocarbonyloxy group, methylaminocarbonyloxy group, ethylaminocarbonyloxy group, (methoxymethyl)aminocarbonyloxy group, (2-methoxyethyl)aminocarbonyloxy group, (cyanomethyl)aminocarbonyloxy group, (2 -Cyanoethyl) aminocarbonyloxy group, dimethylaminocarbonyloxy group, ethylmethylaminocarbonyloxy group, diethylaminocarbonyloxy group, (methoxymethyl) methylaminocarbonyloxy group, (2-methoxyethyl) methylaminocarbonyloxy group, (cyanomethyl ) methylaminocarbonyloxy group, (2-cyanoethyl)methylaminocarbonyloxy group, 2,2-difluoroethylaminocarbonyloxy group, 2,2,2-trifluoroethylaminocarbonyloxy group, cyclopropylaminocarbonyloxy group, (cyclopropyl)methylaminocarbonyloxy group, pyrrolidinylcarbonyloxy group and piperidinylcarbonyloxy group, more preferably acetyloxy group, methoxyacetyloxy group, cyanoacetyloxy group, difluoroacetyloxy group, a trifluoroacetyloxy group, a methoxycarbonyloxy group, an ethoxycarbonyloxy group, an aminocarbonyloxy group, a dimethylaminocarbonyloxy group, an ethylmethylaminocarbonyloxy group, and a diethylaminocarbonyloxy group;

"Rx2C(=O)N(Rx3)-" in R5 of formula (1) (wherein Rx2 is a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 A haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or RaRbN— (wherein Ra and Rb are ), and Rx3 represents a hydrogen atom, a C1 to C6 alkyl group optionally substituted with a substituent B, a C1 to C6 haloalkyl group, or a C3 to C8 cycloalkyl group.) The terms are synonymous with the definitions given above. Regarding the "C1-C6 alkyl group optionally substituted with a substituent B", when the substituent B is present, the hydrogen atom in the C1-C6 alkyl group is optionally substituted with the substituent B. .

Rx2 is preferably a hydrogen atom, a methyl group, a methoxymethyl group, a cyanomethyl group, an ethyl group, a difluoromethyl group, a trifluoromethyl group, a cyclopropyl group, a methoxy group, an ethoxy group, 2,2-difluoroethoxy, 2, 2,2-trifluoroethoxy group, cyclopropyloxy group, amino group, methylamino group, ethylamino group, (methoxymethyl) amino group, (2-methoxyethyl) amino group, (cyanomethyl) amino group, (2- cyanoethyl)amino group, dimethylamino group, ethylmethylamino group, diethylamino group, (methoxymethyl)methylamino group, (2-methoxyethyl)methylamino group, (cyanomethyl)methylamino group, (2-cyanoethyl)methylamino group , 2,2-difluoroethylamino group, 2,2,2-trifluoroethylamino group, cyclopropylamino group, (cyclopropyl)methylamino group, pyrrolidinyl group or piperidinyl group, more preferably a hydrogen atom , methyl group, methoxymethyl group, cyanomethyl group, difluoromethyl group, trifluoromethyl group, methoxy group, ethoxy group, amino group, dimethylamino group, ethylmethylamino group or diethylamino group. Rx3 is preferably a hydrogen atom, a methyl group, a methoxymethyl group, an ethoxymethyl group, a cyanomethyl group, an ethyl group, a 2-methoxyethyl group, a 2-ethoxyethyl group, a 2-cyanoethyl group, a propyl group, 2, a 2-difluoroethyl group, a 2,2,2-trifluoroethyl group, or a cyclopropyl group, more preferably a hydrogen atom, a methyl group, a methoxymethyl group, a cyanomethyl group, an ethyl group, a 2-methoxyethyl group, 2,2-difluoroethyl group or 2,2,2-trifluoroethyl group.

"Rx4Rx5C=NO-" for R5 in formula (1) (where Rx4 and Rx5 are each independently a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group, or RaRbN- (wherein Ra and Rb are ) has the same meaning as defined above. Regarding the "C1-C6 alkyl group optionally substituted with a substituent B", when the substituent B is present, the hydrogen atom in the C1-C6 alkyl group is optionally substituted with the substituent B. .

Rx4 and Rx5 are preferably methyl group, ethyl group, propyl group, isopropyl group, trifluoromethyl group, 2,2,2-trifluoroethyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group, methoxy group and ethoxy group , isopropyloxy group, difluoromethoxy group, trifluoromethoxy group, 2,2-difluoroethoxy group, 2,2,2-trifluoroethoxy group, cyclopropyloxy group, cyclobutyloxy group, cyclopentyloxy group, amino group, methylamino group, ethylamino group, (methoxymethyl)amino group, (2-methoxyethyl)amino group, (cyanomethyl)amino group, (2-cyanoethyl)amino group, dimethylamino group, ethylmethylamino group, diethylamino group, (Methoxymethyl)methylamino group, (2-methoxyethyl)methylamino group, (cyanomethyl)methylamino group, (2-cyanoethyl)methylamino group, 2,2-difluoroethylamino group, 2,2,2-tri fluoroethylamino group, cyclopropylamino group, (cyclopropyl)methylamino group, pyrrolidinyl group or piperidinyl group, more preferably methyl group, ethyl group, trifluoromethyl group, 2,2,2-trifluoro ethyl group, methoxy group, ethoxy group, 2,2,2-trifluoroethoxy group, dimethylamino group, ethylmethylamino group or diethylamino group.

The "3- to 6-membered ring group containing 1 to 2 oxygen atoms" for R5 in formula (1) has the same meaning as defined above, and is preferably an oxolanyl group, an oxanyl group, or a 1,3-dioxolanyl group. , or a 1,3-dioxanyl group, more preferably a 1,3-dioxolanyl group or a 1,3-dioxanyl group.

Y in the formula (1) will be described in detail below.

で表される部分構造（ここで、Ｒ４およびＲ５は前記と同義であり、ｍａは０～４の整数を表す。）を表す。A) When Y is a phenyl group, Y is represented by formula (k)

represents a partial structure represented by (here, R4 and R5 are as defined above, and ma represents an integer of 0 to 4).

ma in the formula (k) represents an integer of 0-4.

When ma in formula (k) is 2 or more, 2 or more R5 each represent an independent substituent, may be the same or different, and can be arbitrarily selected.

As used herein, when Y is a phenyl group, the ortho position means the position of the phenyl group where the substituent R4 is located, as shown in formula (k).

A phenyl group in which the substituent R4 is located in the ortho position is characteristic of the invention.

Preferred combinations of substituents in formula (k) are 2-R4-phenyl group, 2-R4-6-R5-phenyl group, 2-R4-4-R5-phenyl group, 2-R4-4-R5-6 -R5-phenyl group, 2-R4-3-R5-phenyl group, or 2-R4-3-R5-4-R5-6-R5-phenyl group, and a more preferred combination of substituents is 2-R4 -phenyl group, or 2-R4-4-R5-6-R5-phenyl group. Here, for example, "2-R4-6-R5-phenyl group" means a disubstituted phenyl group having a substituent R4 at the 2-position and a substituent R5 at the 6-position, and the same applies to the following description.

で表される部分構造（ここで、Ｒ４、Ｒ５は前記と同義であり、ｍｂは０～３の整数を表す。）を表す。B) When Y is a pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, or tetrazinyl group, Y is represented by formula (L)

represents a partial structure represented by (here, R4 and R5 are as defined above, and mb represents an integer of 0 to 3).

G30, G31, G32 and G33 in formula (L) each independently represent a carbon atom or a nitrogen atom. However, at least one of G30, G31, G32 and G33 is a nitrogen atom. Any one of G30, G31, G32 and G33 is preferably a nitrogen atom. That is, it is a pyridyl group.

mb in formula (L) represents an integer of 0-3.

When mb in formula (L) is 2 or more, 2 or more R5 each represent an independent substituent, may be the same or different, and can be arbitrarily selected.

In this specification, when Y is a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, or a tetrazinyl group, the ortho position means a 6-membered ring having a substituent R4, as shown in formula (L). means the position of

Specific examples of the partial structure represented by formula (L) are shown below.

A pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl or tetrazinyl group in which the substituent R4 is in the ortho position is a feature of the invention.

Preferred specific examples of formula (L) are 3-R4-pyridin-2-yl group, 3-R4-5-R5-pyridin-2-yl group, 2-R4-pyridin-3-yl group, 2-R4 -4-R5-pyridin-3-yl group, 2-R4-6-R5-pyridin-3-yl group, 2-R4-4-R5-6-R5-pyridin-3-yl group, 4-R4- pyridin-3-yl group, 4-R4-2-R5-pyridin-3-yl group, 4-R4-6-R5-pyridin-3-yl group, 4-R4-2-R5-6-R5-pyridine -3-yl group, 3-R4-pyridin-4-yl group, or 3-R4-5-R5-pyridin-4-yl group.

式（ｍ－２）

または、式（ｍ－３）

で表される部分構造（ここで、Ｒ４およびＲ５は前記と同義であり、ｍｃは０～２の整数を表す。）を表す。C) when Y is a thienyl group, a thiazolyl group, an isothiazolyl group, or a thiadiazolyl group, Y is the formula (m-1)

Formula (m-2)

Or, formula (m-3)

represents a partial structure represented by (here, R4 and R5 are as defined above, and mc represents an integer of 0 to 2).

G34 and G35 in formulas (m-1), (m-2) and (m-3) each independently represent a carbon atom or a nitrogen atom.

mc in formula (m-1), formula (m-2) and formula (m-3) represents an integer of 0-2.

When mc of formula (m-1), formula (m-2) and formula (m-3) is 2, R5 of 2 each represents an independent substituent, which may be the same or different, and optionally can do.

In this specification, when Y is a thienyl group, a thiazolyl group, an isothiazolyl group, or a thiadiazolyl group, the ortho position is represented by formula (m-1), formula (m-2) and formula (m-3). at the 5-membered ring position at which R4 is located.

Specific examples of the partial structure represented by formula (m-1) are shown below.

Specific examples of the partial structure represented by formula (m-2) are shown below.

Specific examples of the partial structure represented by formula (m-3) are shown below.

A thienyl, thiazolyl, isothiazolyl or thiadiazolyl group with R4 in the ortho position is a feature of the invention.

Z1 in formula (1) represents C—R6 or a nitrogen atom, and Z2 represents C—R7 or a nitrogen atom. At least one of said Z1 and said Z2 represents a nitrogen atom.
Among them, Z1 is preferably a nitrogen atom, and Z2 is preferably CR7.

（式中、Ｒ１、Ｒ２、Ｒ７、ＸおよびＹは、式（１）と同義である。）で表される化合物、またはその塩を表す。When Z1 in formula (1) is a nitrogen atom and Z2 is C—R7, formula (Za)

(In the formula, R1, R2, R7, X and Y have the same meanings as in formula (1).) or a salt thereof.

（式中、Ｒ１、Ｒ２、Ｒ６、ＸおよびＹは、式（１）と同義である。）で表される化合物、またはその塩を表す。When Z1 in formula (1) is C—R6 and Z2 is a nitrogen atom, formula (Zb)

(wherein, R1, R2, R6, X and Y have the same meanings as in formula (1)) or a salt thereof.

（式中、Ｒ１、Ｒ２、ＸおよびＹは、式（１）と同義である。）で表される化合物、またはその塩を表す。When Z1 in formula (1) is a nitrogen atom and Z2 is a nitrogen atom, formula (Zc)

(In the formula, R1, R2, X and Y are synonymous with formula (1).) or a salt thereof.

R6 is a hydrogen atom, a halogen atom, a C1-C6 alkyl group optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with a substituent A , a C2-C6 alkenyl group optionally substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group optionally substituted with a substituent A, a C2-C6 haloalkynyl group , a C1-C6 alkoxy group optionally substituted with a substituent A, a C1-C6 haloalkoxy group, or Rc-L- (wherein Rc and L are as defined above).

Among them, R6 is a hydrogen atom, a halogen atom, a C1-C6 alkyl group optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cyclo optionally substituted with a substituent A An alkyl group, a C1 to C6 alkoxy group optionally substituted with a substituent A, or a C1 to C6 haloalkoxy group are preferred, and furthermore, a hydrogen atom, a halogen atom, C1 optionally substituted with a substituent A A to C6 alkyl group or a C1 to C6 haloalkyl group is preferred, and a hydrogen atom or a halogen atom is particularly preferred.

R6 in formula (1) contains a hydrogen atom.

The halogen atom for R6 in formula (1) has the same meaning as defined above, preferably a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, particularly preferably a chlorine atom.

The C1-C6 alkyl group of the "C1-C6 alkyl group optionally substituted with a substituent A" for R6 in formula (1) has the same meaning as defined above, and is preferably a methyl group or an ethyl group. , propyl, isopropyl, butyl or isobutyl, more preferably methyl, ethyl or propyl. When having a substituent A, a hydrogen atom in the C1-C6 alkyl group is optionally substituted by the substituent A.

The “C1-C6 haloalkyl group” for R6 in formula (1) has the same meaning as defined above, and is preferably a difluoromethyl group, a trifluoromethyl group, a 2-fluoroethyl group, or a 2,2-difluoroethyl group. , 2,2,2-trifluoroethyl group, 3,3-difluoropropyl group, or 3,3,3-trifluoropropyl group, more preferably difluoromethyl group, trifluoromethyl group, 2-fluoro It is an ethyl group, a 2,2-difluoroethyl group, or a 2,2,2-trifluoroethyl group.

The C3-C8 cycloalkyl group of the "C3-C8 cycloalkyl group optionally substituted with a substituent A" for R6 in formula (1) is as defined above, preferably a cyclopropyl group , cyclobutyl group, cyclopentyl group or cyclohexyl group, more preferably cyclopropyl group or cyclobutyl group. A hydrogen atom in the C3-C8 cycloalkyl group is optionally replaced by the substituent A, if the substituent A is present.

The C2-C6 alkenyl group of the "C2-C6 alkenyl group optionally substituted with a substituent A" for R6 in formula (1) has the same meaning as defined above, preferably a vinyl group, 1- It is a propenyl group or an allyl group, more preferably a vinyl group or an allyl group. A hydrogen atom in the C2-C6 alkenyl group is optionally replaced by the substituent A, if the substituent A is present.

The "C2-C6 haloalkenyl group" for R6 in formula (1) has the same meaning as defined above, preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, a 3-fluoroallyl group, or It is a 3,3-difluoroallyl group, more preferably a 2-fluorovinyl group or a 2,2-difluorovinyl group.

The C2-C6 alkynyl group of the "C2-C6 alkynyl group optionally substituted with a substituent A" for R6 in formula (1) has the same meaning as defined above, preferably an ethynyl group, 1- It is a propynyl group, propargyl group, 2-butynyl group or 3-butynyl group, more preferably an ethynyl group, 1-propynyl group or propargyl group. A hydrogen atom in the C2-C6 alkynyl group is optionally replaced by the substituent A, if the substituent A is present.

The “C2-C6 haloalkynyl group” for R6 in formula (1) has the same meaning as defined above, preferably 3,3-difluoro-1-propynyl group, 3,3,3-trifluoro-1 -propynyl group, 4,4-difluoro-2-butynyl group, 4-chloro-4,4-difluoro-2-butynyl group, 4-bromo-4,4-difluoro-2-butynyl group, or 4,4, 4-trifluoro-2-butynyl group, more preferably 3,3-difluoro-1-propynyl group and 3,3,3-trifluoro-1-propynyl group.

The C1-C6 alkoxy group of the "C1-C6 alkoxy group optionally substituted with a substituent A" for R6 in formula (1) has the same definition as above, preferably a methoxy group or an ethoxy group. , propyloxy, isopropyloxy, butoxy or isobutoxy, more preferably methoxy or ethoxy. When having a substituent A, a hydrogen atom in the C1-C6 alkoxy group is optionally replaced by the substituent A.

The “C1-C6 haloalkoxy group” for R6 in formula (1) has the same meaning as defined above, preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, 2,2, 2-trifluoroethoxy group, 3,3-difluoropropyloxy group or 3,3,3-trifluoropropyloxy group, more preferably difluoromethoxy group, trifluoromethoxy group and 2,2-difluoroethoxy or a 2,2,2-trifluoroethoxy group.

Rc and L of "Rc-L-" in R6 of formula (1) are the same as defined above. "Rc-L-" is preferably a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, a trifluoromethanesulfinyl group, and a trifluoromethanesulfonyl group, more preferably a methylthio group and a methanesulfinyl group. , and a methanesulfonyl group.

R7 is a hydrogen atom, a halogen atom, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with a substituent A, a C2-C6 alkenyl group optionally substituted with a substituent A , a C2-C6 haloalkenyl group, a C2-C6 alkynyl group optionally substituted with a substituent A, a C2-C6 haloalkynyl group, a C1-C6 alkoxy group optionally substituted with a substituent A , a C1-C6 haloalkoxy group, Rc-L- (wherein Rc and L are as defined above), or Rx1C(=O)- (wherein Rx1 is as defined above. ).

Among them, R7 is a hydrogen atom, a halogen atom, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with a substituent A, a C1-C6 optionally substituted with a substituent A An alkoxy group or a C1-C6 haloalkoxy group is preferred, a hydrogen atom or a halogen atom is more preferred, and a hydrogen atom is particularly preferred.

A hydrogen atom is included in R7 in Formula (1).

The halogen atom for R7 in formula (1) has the same meaning as defined above, and is preferably a fluorine atom, chlorine atom, bromine atom or iodine atom.

The “C1-C6 haloalkyl group” for R7 in formula (1) has the same meaning as defined above, preferably 2-fluoroethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoro ethyl group, 3,3-difluoropropyl group or 3,3,3-trifluoropropyl group, more preferably 2-fluoroethyl group, 2,2-difluoroethyl group or 2,2,2- It is a trifluoroethyl group.

The C3-C8 cycloalkyl group of the "C3-C8 cycloalkyl group optionally substituted with a substituent A" for R7 in formula (1) has the same definition as above, preferably a cyclopropyl group. , cyclobutyl group, cyclopentyl group or cyclohexyl group, more preferably cyclopropyl group or cyclobutyl group. A hydrogen atom in the C3-C8 cycloalkyl group is optionally replaced by the substituent A, if the substituent A is present.

The C2-C6 alkenyl group of the "C2-C6 alkenyl group optionally substituted with a substituent A" for R7 in formula (1) has the same definition as above, preferably a vinyl group, 1- It is a propenyl group or an allyl group, more preferably a vinyl group or an allyl group. A hydrogen atom in the C2-C6 alkenyl group is optionally replaced by the substituent A, if the substituent A is present.

The “C2-C6 haloalkenyl group” for R7 in formula (1) has the same meaning as defined above, preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, a 3-fluoroallyl group, or It is a 3,3-difluoroallyl group, more preferably a 2-fluorovinyl group or a 2,2-difluorovinyl group.

The C2-C6 alkynyl group of the "C2-C6 alkynyl group optionally substituted with a substituent A" for R7 in formula (1) has the same meaning as defined above, preferably an ethynyl group, 1- It is a propynyl group, propargyl group, 2-butynyl group or 3-butynyl group, more preferably an ethynyl group, 1-propynyl group or propargyl group. A hydrogen atom in the C2-C6 alkynyl group is optionally replaced by the substituent A, if the substituent A is present.

The “C2-C6 haloalkynyl group” for R7 in formula (1) has the same meaning as defined above, preferably 3,3-difluoro-1-propynyl group, 3,3,3-trifluoro-1 -propynyl group, 4,4-difluoro-2-butynyl group, 4-chloro-4,4-difluoro-2-butynyl group, 4-bromo-4,4-difluoro-2-butynyl group, or 4,4, 4-trifluoro-2-butynyl group, more preferably 3,3-difluoro-1-propynyl group, 3,3,3-trifluoro-1-propynyl group, 4,4-difluoro-2-butynyl group or 4,4,4-trifluoro-2-butynyl group.

The C1-C6 alkoxy group of the "C1-C6 alkoxy group optionally substituted with a substituent A" for R7 in formula (1) has the same definition as above, preferably a methoxy group or an ethoxy group. , propyloxy, isopropyloxy, butoxy or isobutoxy, more preferably methoxy or ethoxy. When having a substituent A, a hydrogen atom in the C1-C6 alkoxy group is optionally replaced by the substituent A.

The “C1-C6 haloalkoxy group” for R7 in formula (1) has the same meaning as defined above, preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, 2,2, 2-trifluoroethoxy group, 3,3-difluoropropyloxy group or 3,3,3-trifluoropropyloxy group, more preferably difluoromethoxy group, trifluoromethoxy group and 2,2-difluoroethoxy or a 2,2,2-trifluoroethoxy group.

Rc and L of "Rc-L-" in R7 of formula (1) are the same as defined above. "Rc-L-" is preferably a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, a trifluoromethanesulfinyl group, and a trifluoromethanesulfonyl group, more preferably a methylthio group and a methanesulfinyl group. , and a methanesulfonyl group.

Rx1 of "Rx1C(=O)-" in R7 of formula (1) has the same meaning as defined above. "Rx1C(=O)-" is preferably an acetyl group, a methoxyacetyl group, a cyanoacetyl group, a propionyl group, a difluoroacetyl group, a trifluoroacetyl group, a cyclopropanecarbonyl group, a methoxycarbonyl group, an ethoxycarbonyl group, 2 , 2-difluoroethoxycarbonyl group, 2,2,2-trifluoroethoxycarbonyl group, 3,3,3-trifluoropropyloxycarbonyl group, cyclopropyloxycarbonyl group, aminocarbonyl group, methylaminocarbonyl group, ethylamino carbonyl group, (methoxymethyl)aminocarbonyl group, (2-methoxyethyl)aminocarbonyl group, (cyanomethyl)aminocarbonyl group, (2-cyanoethyl)aminocarbonyl group, dimethylaminocarbonyl group, ethylmethylaminocarbonyl group, diethylaminocarbonyl group, (methoxymethyl)methylaminocarbonyl group, (2-methoxyethyl)methylaminocarbonyl group, (cyanomethyl)methylaminocarbonyl group, (2-cyanoethyl)methylaminocarbonyl group, 2,2-difluoroethylaminocarbonyl group, 2,2,2-trifluoroethylaminocarbonyl group, cyclopropylaminocarbonyl group, (cyclopropyl)methylaminocarbonyl group, pyrrolidinylcarbonyl group, and piperidinylcarbonyl group, more preferably acetyl group, methoxyacetyl group, cyanoacetyl group, difluoroacetyl group, trifluoroacetyl group, methoxycarbonyl group, ethoxycarbonyl group, aminocarbonyl group, dimethylaminocarbonyl group, ethylmethylaminocarbonyl group, and diethylaminocarbonyl group.

X in Formula (1) represents an oxygen atom or a sulfur atom. Preferred X is an oxygen atom.

The "substituent A" of formula (1) is a hydroxyl group, a cyano group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, RaRbN- (Here, Ra and Rb are as defined above.) and Rc-L- (Here, Rc and L are as defined above.) Represents at least one selected from the group consisting of .

Among them, the substituent A is preferably a cyano group, a C1 to C6 alkoxy group, and Rc-L- (wherein Rc and L are as defined above), particularly a cyano group and a C1 to C6 Alkoxy groups are preferred.

Preferred specific examples of the substituent A include a hydroxyl group, a cyano group,
cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl groups as C3-C8 cycloalkyl groups;
C1-C6 alkoxy groups include methoxy, ethoxy, propyloxy, and isopropyloxy groups,
The C1 to C6 haloalkoxy groups include a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 3,3-difluoropropyloxy group, and a 3,3 , 3-trifluoropropyloxy group,
C3-C8 cycloalkoxy groups include cyclopropyloxy, cyclobutoxy, cyclopentyloxy, and cyclohexyloxy groups,
RaRbN- (wherein Ra and Rb are as defined above) is an amino group, methylamino group, ethylamino group, (methoxymethyl)amino group, (2-methoxyethyl)amino group, (cyanomethyl) amino group, (2-cyanoethyl)amino group, dimethylamino group, ethylmethylamino group, diethylamino group, (methoxymethyl)methylamino group, (2-methoxyethyl)methylamino group, (cyanomethyl)methylamino group, (2 -cyanoethyl)methylamino group, 2,2-difluoroethylamino group, 2,2,2-trifluoroethylamino group, cyclopropylamino group, (cyclopropyl)methylamino group, pyrrolidinyl group, and piperidinyl group, and Rc-L- (wherein Rc and L are as defined above) is a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, a trifluoromethanesulfinyl group, and a trifluoromethanesulfonyl group. .

More preferred specific examples of the substituent A include a hydroxyl group; a cyano group;
As the C3-C8 cycloalkyl group, a cyclopropyl group and a cyclobutyl group,
C1-C6 alkoxy groups, methoxy group and ethoxy group,
as the C1-C6 haloalkoxy groups, a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group and a 2,2,2-trifluoroethoxy group;
cyclopropyloxy group and cyclobutoxy group as C3-C8 cycloalkoxy groups,
RaRbN- (wherein Ra and Rb are as defined above) are a dimethylamino group, an ethylmethylamino group, and a diethylamino group,
and Rc-L- (wherein Rc and L are as defined above) are a methylthio group, a methanesulfinyl group and a methanesulfonyl group.

The "substituent B" in formula (1) represents at least one selected from the group consisting of a cyano group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, and a C3-C8 cycloalkoxy group. .

Among them, the substituent B is preferably a cyano group and a C1-C6 alkoxy group.

With respect to preferred specific examples of substituent B, a cyano group;
methoxy, ethoxy, propyloxy, and isopropyloxy groups as C1-C6 alkoxy groups;
The C1 to C6 haloalkoxy groups include a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 3,3-difluoropropyloxy group, and a 3,3 , 3-trifluoropropyloxy group;
and C3-C8 cycloalkoxy groups are cyclopropyloxy, cyclobutoxy, cyclopentyloxy, and cyclohexyloxy.

Further preferred specific examples of the substituent B include a cyano group;
Methoxy group and ethoxy group as C1 to C6 alkoxy groups;
difluoromethoxy, trifluoromethoxy, 2,2-difluoroethoxy, and 2,2,2-trifluoroethoxy groups as C1-C6 haloalkoxy groups;
and C3-C8 cycloalkoxy groups include cyclopropyloxy and cyclobutoxy groups.

The "substituent C" in formula (1) is a hydroxyl group, a cyano group, a C3-C8 cycloalkyl group,
a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, a C2-C6 alkoxyalkoxy group, RaRbN- (wherein Ra and Rb are as defined above), Rc-L- (where Rc and L are as defined above), Rx1C (=O)- (where Rx1 is as defined above), Rx6Rx7Rx8Si- (where Rx6, Rx7 and Each Rx8 independently represents a C1-C6 alkyl group.), and at least one selected from the group consisting of a 3- to 6-membered ring group containing 1 to 2 oxygen atoms.
Among them, the substituent C is a cyano group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C2-C6 alkoxyalkoxy group, Rc-L- (wherein Rc and L is as defined above), Rx1C(=O)- (wherein Rx1 is as defined above), and a 3- to 6-membered ring group containing 1 to 2 oxygen atoms preferably
Particularly preferred are a cyano group, a C1-C6 alkoxy group, and Rc-L- (wherein Rc and L are as defined above).

Preferred specific examples of the substituent C include a hydroxyl group; a cyano group;
cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl groups as C3-C8 cycloalkyl groups;
methoxy, ethoxy, propyloxy, isopropyloxy, butoxy, isobutoxy, and t-butoxy groups as C1-C6 alkoxy groups;
The C1 to C6 haloalkoxy groups include a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 3,3-difluoropropyloxy group, and a 3,3 , 3-trifluoropropyloxy group;
cyclopropyloxy, cyclobutoxy, cyclopentyloxy, and cyclohexyloxy groups as C3-C8 cycloalkoxy groups;
methoxymethoxy, ethoxymethoxy, methoxyethoxy, ethoxyethoxy, and methoxypropyloxy groups as C2-C6 alkoxyalkoxy groups;
RaRbN- (wherein Ra and Rb are as defined above) is an amino group, methylamino group, ethylamino group, (methoxymethyl)amino group, (2-methoxyethyl)amino group, (cyanomethyl) amino group, (2-cyanoethyl)amino group, dimethylamino group, ethylmethylamino group, diethylamino group, (methoxymethyl)methylamino group, (2-methoxyethyl)methylamino group, (cyanomethyl)methylamino group, (2 -cyanoethyl)methylamino group, 2,2-difluoroethylamino group, 2,2,2-trifluoroethylamino group, cyclopropylamino group, (cyclopropyl)methylamino group, pyrrolidinyl group, and piperidinyl group;
Rc-L- (wherein Rc and L are as defined above), a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, a trifluoromethanesulfinyl group, and a trifluoromethanesulfonyl group;
Rx1C(=O)- (here, Rx1 has the same definition as above) is an acetyl group, a methoxyacetyl group, a cyanoacetyl group, a propionyl group, a difluoroacetyl group, a trifluoroacetyl group, a cyclopropanecarbonyl group, methoxycarbonyl group, ethoxycarbonyl group, 2,2-difluoroethoxycarbonyl group, 2,2,2-trifluoroethoxycarbonyl group, 3,3,3-trifluoropropyloxycarbonyl group, cyclopropyloxycarbonyl group, aminocarbonyl group, methylaminocarbonyl group, ethylaminocarbonyl group, (methoxymethyl)aminocarbonyl group, (2-methoxyethyl)aminocarbonyl group, (cyanomethyl)aminocarbonyl group, (2-cyanoethyl)aminocarbonyl group, dimethylaminocarbonyl group , ethylmethylaminocarbonyl group, diethylaminocarbonyl group, (methoxymethyl)methylaminocarbonyl group, (2-methoxyethyl)methylaminocarbonyl group, (cyanomethyl)methylaminocarbonyl group, (2-cyanoethyl)methylaminocarbonyl group, 2 ,2-difluoroethylaminocarbonyl group, 2,2,2-trifluoroethylaminocarbonyl group, cyclopropylaminocarbonyl group, (cyclopropyl)methylaminocarbonyl group, pyrrolidinylcarbonyl group, and piperidinylcarbonyl group;
Rx6Rx7Rx8Si- (wherein Rx6, Rx7 and Rx8 are as defined above), a trimethylsilyl group and a triethylsilyl group;
and 3- to 6-membered ring groups containing 1 to 2 oxygen atoms are oxolanyl, oxanyl, 1,3-dioxolanyl and 1,3-dioxanyl groups.

More preferred specific examples of the substituent C include a hydroxyl group; a cyano group;
cyclopropyl group and cyclobutyl group as C3-C8 cycloalkyl groups;
Methoxy group and ethoxy group as C1 to C6 alkoxy groups;
difluoromethoxy, trifluoromethoxy, 2,2-difluoroethoxy, and 2,2,2-trifluoroethoxy groups as C1-C6 haloalkoxy groups;
cyclopropyloxy group and cyclobutoxy group as C3-C8 cycloalkoxy groups;
methoxymethoxy, ethoxymethoxy, methoxyethoxy, and ethoxyethoxy groups as C2-C6 alkoxyalkoxy groups;
RaRbN- (wherein Ra and Rb are as defined above) are a dimethylamino group, an ethylmethylamino group, and a diethylamino group;
Rc-L- (wherein Rc and L are as defined above), a methylthio group, a methanesulfinyl group, and a methanesulfonyl group;
Rx1C(=O)- (here, Rx1 has the same definition as above) includes an acetyl group, a methoxyacetyl group, a cyanoacetyl group, a difluoroacetyl group, a trifluoroacetyl group, a methoxycarbonyl group, an ethoxycarbonyl group, aminocarbonyl group, dimethylaminocarbonyl group, ethylmethylaminocarbonyl group, and diethylaminocarbonyl group;
Rx6Rx7Rx8Si- (wherein Rx6, Rx7 and Rx8 are as defined above), a trimethylsilyl group;
and 3- to 6-membered ring groups containing 1 to 2 oxygen atoms are 1,3-dioxolanyl and 1,3-dioxanyl groups.

The "substituent D" in formula (1) means a hydroxyl group, a cyano group, a nitro group, a halogen atom, a C1 to C6 alkyl group optionally substituted by a substituent B, a C1 to C6 haloalkyl group, a C3 to C8 a cycloalkyl group, a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group,
and at least one selected from the group consisting of C3-C8 cycloalkoxy groups.

Among them, the substituent D is a cyano group, a halogen atom, a C1 to C6 alkyl group optionally substituted with a substituent B, a C1 to C6 haloalkyl group, a C1 to C6 alkoxy group and a C1 to C6 haloalkoxy group. is preferred.

With respect to preferred specific examples of substituent D,
as halogen atoms, a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom;
hydroxyl group; cyano group; nitro group;
Examples of C1 to C6 alkyl groups optionally substituted by substituent B include methyl group, methoxymethyl group, ethoxymethyl group, cyanomethyl group, ethyl group, 2-methoxyethyl group, 2-ethoxyethyl group, and 2-cyanoethyl. group, propyl group, isopropyl group, butyl group, and isobutyl group;
The C1 to C6 haloalkyl groups include difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 3,3-difluoropropyl, and 3,3,3 - a trifluoropropyl group;
cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl groups as C3-C8 cycloalkyl groups;
methoxy, ethoxy, propyloxy, isopropyloxy, butoxy, isobutoxy, and t-butoxy groups as C1-C6 alkoxy groups;
The C1 to C6 haloalkoxy groups include a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 3,3-difluoropropyloxy group, and a 3,3 , 3-trifluoropropyloxy group;
and the C3-C8 cycloalkoxy groups are cyclopropyloxy, cyclobutoxy, cyclopentyloxy, and cyclohexyloxy.

With respect to more preferred specific examples of the substituent D,
as halogen atoms, a fluorine atom, a chlorine atom, and a bromine atom;
hydroxyl group; cyano group; nitro group;
Examples of the C1 to C6 alkyl groups optionally substituted by the substituent B include a methyl group, a methoxymethyl group, an ethoxymethyl group, a cyanomethyl group, an ethyl group, a 2-methoxyethyl group, a 2-ethoxyethyl group, and a 2- cyanoethyl group;
a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, and a 2,2,2-trifluoroethyl group as the C1 to C6 haloalkyl groups;
cyclopropyl group and cyclobutyl group as C3-C8 cycloalkyl groups;
methoxy, ethoxy, propyloxy, and isopropyloxy groups as C1-C6 alkoxy groups;
difluoromethoxy, trifluoromethoxy, 2,2-difluoroethoxy, and 2,2,2-trifluoroethoxy groups as C1-C6 haloalkoxy groups;
and C3-C8 cycloalkoxy groups include cyclopropyloxy and cyclobutoxy groups.

The compounds represented by formula (1) may have 1 or 2 axial asymmetries. The isomer ratio at this time is not particularly limited, and may be a single isomer ratio or an arbitrary mixing ratio.

The compound represented by formula (1) may contain an asymmetric atom. The isomer ratio at this time is not particularly limited, and may be a single isomer ratio or an arbitrary mixing ratio.

The compound represented by Formula (1) may contain geometric isomers. The isomer ratio at this time is not particularly limited, and may be a single isomer ratio or an arbitrary mixing ratio.

Compounds of formula (1) may be capable of forming salts. Examples include acid salts such as hydrochloric acid, sulfuric acid, acetic acid, fumaric acid, and maleic acid, and metal salts such as sodium, potassium, and calcium. no.

Preferred ranges of R1, R2, R3, R4, R5, R6, R7, X, Y, Z1, Z2, substituent A, substituent B, substituent C, and substituent D described above can be obtained by arbitrarily combining them. The scope of all compounds of Formula (1) of the present invention or intermediate compounds thereof is also set forth herein.

Next, specific compounds of the present invention are represented by structural formulas P-1 to P-44 shown in Table 1 (where X in Table 1 represents an oxygen atom or a sulfur atom) and Table 2. Structural formulas (Y-1 to Y-408) of Y shown (where Y is as defined above) and formulas (wherein R2 is as defined above) shown in Table 3 (wherein R2 is as defined above) R2-1 to R2-5214). These compounds are for illustration and the invention is not limited to them.

A method for producing the compound represented by formula (1) is exemplified below.

式中、Ｒ１は、水酸基、シアノ基、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
Ｃ２～Ｃ６のハロアルキニル基、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニルオキシ基、
Ｃ２～Ｃ６のハロアルケニルオキシ基、置換基Ａで適宜置換されてもよいＣ３～Ｃ６のアルキニルオキシ基、Ｃ３～Ｃ６のハロアルキニルオキシ基、またはＲａＲｂＮ－（ここで、ＲａおよびＲｂは、それぞれ独立していて、水素原子、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、またはＣ３～Ｃ８のシクロアルキル基を表すか、あるいはＲａおよびＲｂは、結合する窒素原子と一緒になって、アジリジニル基、アゼチジニル基、ピロリジニル基、ピペリジニル基、ホモピペリジニル基、またはアゾカニル基を形成するものを表す。）を表し、
Ｒ２は、シアノ基、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、ＲａＲｂＮ－（ここで、ＲａおよびＲｂは前記と同義である。）、Ｒｘ１Ｃ（＝Ｏ）－（ここで、Ｒｘ１は、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、またはＲａＲｂＮ－（ここで、ＲａおよびＲｂは前記と同義である。）を表す。）、フェニル基、５員～６員の複素環基、または８～１０員の複素環基を表し、
該フェニル基は、Ｒ３が適宜０～５置換し（ただし、２置換以上のＲ３がある場合、Ｒ３はそれぞれ独立した置換基を表す。）、
該５～６員の複素環基、または該８～１０員の複素環基は、Ｒ３が適宜０～６置換し（ただし、２置換以上のＲ３がある場合、Ｒ３はそれぞれ独立した置換基を表す。）、
Ｙは、フェニル基、ピリジル基、ピリダジニル基、ピリミジニル基、ピラジニル基、トリアジニル基、テトラジニル基、チエニル基、チアゾリル基、イソチアゾリル基、またはチアジアゾリル基を表し、
該フェニル基は、Ｒ４がオルト位に置換し、さらにＲ５が適宜０～４置換し（ただし、２置換以上のＲ５がある場合、Ｒ５はそれぞれ独立した置換基を表す。）、
該ピリジル基、該ピリダジニル基、該ピリミジニル基、該ピラジニル基、該トリアジニル基、または該テトラジニル基は、Ｒ４がオルト位に置換し、さらにＲ５が適宜０～３置換し（ただし、２置換以上のＲ５がある場合、Ｒ５はそれぞれ独立した置換基を表す。）、
該チエニル基、該チアゾリル基、該イソチアゾリル基、または該チアジアゾリル基は、Ｒ４がオルト位に置換し、さらにＲ５が適宜０～２置換し（ただし、２置換以上のＲ５がある場合、Ｒ５はそれぞれ独立した置換基を表す。）、
Ｒ４は、水酸基、シアノ基、ニトロ基、ハロゲン原子、置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６ハロアルケニル基、置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニルオキシ基、Ｃ２～Ｃ６のハロアルケニルオキシ基、置換基Ｃで適宜置換されてもよいＣ３～Ｃ６のアルキニルオキシ基、Ｃ３～Ｃ６のハロアルキニルオキシ基、置換基Ｄで適宜置換されてもよいアリール基、置換基Ｄで適宜置換されてもよいヘテロアリール基、
置換基Ｄで適宜置換されてもよいアラルキルオキシ基、ＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）、Ｒｃ－Ｌ－（ここで、ＲｃおよびＬは、前記と同義である。）、Ｒｘ１Ｃ（＝Ｏ）－（ここでＲｘ１は、前記と同義である。）、Ｒｘ１Ｃ（＝Ｏ）Ｏ－（ここでＲｘ１は、前記と同義である。）、Ｒｘ２Ｃ（＝Ｏ）Ｎ（Ｒｘ３）－（ここで、Ｒｘ２は、水素原子、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、またはＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）を表し、Ｒｘ３は、水素原子、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、またはＣ３～Ｃ８のシクロアルキル基を表す。）、Ｒｘ４Ｒｘ５Ｃ＝Ｎ－Ｏ－（ここで、Ｒｘ４およびＲｘ５は、それぞれ独立していて、水素原子、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、またはＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）を表す。）、または１～２個の酸素原子を含む３～６員環の基を表し、
Ｒ５は、前記に記載のＲ４と同義であり、
Ｒ７は、水素原子、ハロゲン原子、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｒｃ－Ｌ－（ここで、ＲｃおよびＬは、前記と同義である。）、Ｒｘ１Ｃ（＝Ｏ）－（ここで、Ｒｘ１は、前記と同義である。）を表し、
Ｘは、酸素原子、または硫黄原子を表す。[Manufacturing method A]

In the formula, R1 is a hydroxyl group, a cyano group, a C1-C6 alkyl group optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cyclo optionally substituted with a substituent A an alkyl group, a C2-C6 alkenyl group optionally substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group optionally substituted with a substituent A,
C2-C6 haloalkynyl group, C1-C6 alkoxy group optionally substituted with substituent A, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group optionally substituted with substituent A , a C2-C6 alkenyloxy group optionally substituted with a substituent A,
A C2-C6 haloalkenyloxy group, a C3-C6 alkynyloxy group optionally substituted with a substituent A, a C3-C6 haloalkynyloxy group, or RaRbN— (where Ra and Rb are each independently represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group, or Ra and Rb are a bond together with the nitrogen atom to form an aziridinyl group, azetidinyl group, pyrrolidinyl group, piperidinyl group, homopiperidinyl group, or azocanyl group.)
R2 is a cyano group, a C1-C6 alkyl group optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with a substituent A, a substituent C2-C6 alkenyl group optionally substituted with A, C2-C6 haloalkenyl group, C2-C6 alkynyl group optionally substituted with substituent A, C2-C6 haloalkynyl group, substituent A C1-C6 alkoxy group optionally substituted with A, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group optionally substituted with a substituent A, RaRbN— (where Ra and Rb is as defined above.), Rx1C(=O)-(wherein Rx1 is a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 a cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or RaRbN- (wherein Ra and Rb are as defined above).), represents a phenyl group, a 5- to 6-membered heterocyclic group, or an 8- to 10-membered heterocyclic group,
the phenyl group is optionally substituted with 0 to 5 R3 (provided that when there are two or more substituted R3, each R3 represents an independent substituent);
The 5- to 6-membered heterocyclic group or the 8- to 10-membered heterocyclic group is optionally substituted with 0 to 6 R3 (provided that when there are 2 or more R3s, each R3 is an independent substituent. show.),
Y represents a phenyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, a tetrazinyl group, a thienyl group, a thiazolyl group, an isothiazolyl group, or a thiadiazolyl group;
the phenyl group is substituted with R4 at the ortho position and further optionally substituted with 0 to 4 R5 (provided that when there are two or more substituted R5, each R5 represents an independent substituent);
The pyridyl group, the pyridazinyl group, the pyrimidinyl group, the pyrazinyl group, the triazinyl group, or the tetrazinyl group is substituted with R4 at the ortho position, and optionally with 0 to 3 substituents with R5 (provided that 2 or more substituents are substituted). When R5 is present, each R5 represents an independent substituent.),
In the thienyl group, the thiazolyl group, the isothiazolyl group, or the thiadiazolyl group, R4 is substituted at the ortho position, and R5 is optionally substituted with 0 to 2 (provided that when there are two or more substituted R5, R5 is represents an independent substituent.),
R4 is a hydroxyl group, a cyano group, a nitro group, a halogen atom, a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group optionally substituted with a substituent C, a C3- C8 cycloalkyl group, C2-C6 alkenyl group optionally substituted with substituent C, C2-C6 haloalkenyl group, C2-C6 alkynyl group optionally substituted with substituent C, C2-C6 A haloalkynyl group, a C1 to C6 alkoxy group optionally substituted with a substituent C, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group optionally substituted with a substituent C, a substituent C2-C6 alkenyloxy group optionally substituted with C, C2-C6 haloalkenyloxy group, C3-C6 alkynyloxy group optionally substituted with substituent C, C3-C6 haloalkynyloxy group group, an aryl group optionally substituted with a substituent D, a heteroaryl group optionally substituted with a substituent D,
An aralkyloxy group optionally substituted with a substituent D, RaRbN- (wherein Ra and Rb are as defined above), Rc-L- (wherein Rc and L are as defined above) ), Rx1C(=O)-(wherein Rx1 has the same definition as above.), Rx1C(=O)O-(wherein Rx1 has the same definition as above.), Rx2C(=O) N(Rx3)-(wherein Rx2 is a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 An alkoxy group, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group, or RaRbN— (wherein Ra and Rb are as defined above.), Rx3 is a hydrogen atom, a substituent B represents an optionally substituted C1 to C6 alkyl group, a C1 to C6 haloalkyl group, or a C3 to C8 cycloalkyl group.), Rx4Rx5C=NO- (wherein Rx4 and Rx5 are each independently a hydrogen atom, a C1 to C6 alkyl group optionally substituted with a substituent B, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group, a C1 to C6 alkoxy group, a C1 to represents a C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or RaRbN— (wherein Ra and Rb are as defined above), or 3 to 3 containing 1 to 2 oxygen atoms represents a 6-membered ring group,
R5 has the same definition as R4 described above;
R7 is a hydrogen atom, a halogen atom, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with a substituent A, a C2-C6 alkenyl group optionally substituted with a substituent A , a C2-C6 haloalkenyl group, a C2-C6 alkynyl group optionally substituted with a substituent A, a C2-C6 haloalkynyl group, a C1-C6 alkoxy group optionally substituted with a substituent A , a C1 to C6 haloalkoxy group, Rc-L- (wherein Rc and L are as defined above), Rx1C(=O)- (wherein Rx1 is as defined above.) represents
X represents an oxygen atom or a sulfur atom.

Production method A is a method for obtaining a compound represented by formula (Za) among the compounds represented by formula (1), wherein the compound represented by formula (2) and the compound represented by formula (3) are obtained. and a compound in the presence of an acid.

The compound represented by formula (3) used in this reaction can be obtained as a commercial product or produced by a known method. Formula (3) may be a salt formed with an acidic compound such as hydrochloric acid or acetic acid, and is not particularly limited as long as the intended reaction proceeds.

The compound represented by formula (3) used in this reaction may be in an amount of 1 equivalent or more relative to the compound represented by formula (2), and is not particularly limited as long as the desired reaction proceeds. However, it is preferably from 1 equivalent to 20 equivalents.

Examples of the acid used in this reaction include inorganic acids such as hydrochloric acid and sulfuric acid, and organic acids such as acetic acid, methanesulfonic acid and p-toluenesulfonic acid. p-toluenesulfonic acid is preferred. Moreover, when using the salt with the compound represented by Formula (3), the use of an acid is not essential.

The amount of acid used in this reaction may be 1 equivalent or more with respect to the compound represented by formula (2), and is not particularly limited as long as the intended reaction proceeds. It is 1 equivalent or more and 20 equivalents or less. Moreover, when the acid used is liquid, it can also be used as a solvent.

A solvent can be used in this reaction, but is not essential.

The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds. Ether solvents such as ethane, tetrahydrofuran and dioxane; alcohol solvents such as methanol, ethanol and isopropanol; benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene; Ester solvents, nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone Solvents include halogen-based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride. These solvents can be used singly or as a mixture of two or more at any ratio. The solvent preferably includes an acidic solvent and a benzene-based solvent, and more preferably includes a benzene-based solvent.

The amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times the weight of the compound represented by the formula (3). be.

The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually from 50° C. to 180° C. or below the boiling point of the solvent.

As a post-treatment of the reaction, a liquid separation operation can be performed by adding water or a suitable aqueous solution to the reaction mixture. When using an aqueous solution, use an acidic aqueous solution with hydrochloric acid, sulfuric acid, ammonium chloride, etc. dissolved, an alkaline aqueous solution with potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc. dissolved, or salt water. etc. can be used arbitrarily. During the liquid separation operation, if necessary, benzene solvents such as toluene, xylene, benzene, chlorobenzene, and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate, diethyl ether, diisopropyl ether, methyl- Ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane, which are incompatible with water. It is possible to add In addition, these solvents can be used alone, or two or more of them can be mixed at any ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield.

The reaction mixture containing the compound represented by the formula (Za) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.

The solvent can be distilled off from the reaction mixture containing the compound represented by formula (Za) obtained above under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (Za) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, or the like with an appropriate solvent. It may be appropriately set according to the desired purity.

式中、ＳＲは硫黄化剤を表し、Ｒ１、Ｒ２、Ｒ７、およびＹは、前記と同義である。[Manufacturing method B]

In the formula, SR represents a sulfurizing agent, and R1, R2, R7 and Y are as defined above.

Production method B is a production method for obtaining a compound represented by formula (Za-2) among the compounds represented by formula (1), wherein the compound represented by formula (Za-1) and sulfuration agent (SR) in a solvent.

Sulfurizing agents used in this reaction include Lawesson's reagent (2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide) and the like.

The amount of the sulfurizing agent used in this reaction may be 0.5 equivalents or more with respect to the compound represented by formula (Za-1), and is not particularly limited as long as the desired reaction proceeds. However, it is preferably from 1 equivalent to 10 equivalents.

The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane, Benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, and the like are included. These solvents can be used singly or as a mixture of two or more at any ratio.

The amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times the weight of the compound represented by the formula (Za-1). It is below.

The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually from 50° C. to 180° C. or below the boiling point of the solvent.

As a post-treatment of the reaction, a liquid separation operation can be performed by adding water or a suitable aqueous solution to the reaction mixture. When using an aqueous solution, use an acidic aqueous solution with hydrochloric acid, sulfuric acid, ammonium chloride, etc. dissolved, an alkaline aqueous solution with potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc. dissolved, or salt water. etc. can be used arbitrarily. During the liquid separation operation, if necessary, benzene solvents such as toluene, xylene, benzene, chlorobenzene, and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate, diethyl ether, diisopropyl ether, methyl- Ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane, which are incompatible with water. It is possible to add In addition, these solvents can be used alone, or two or more of them can be mixed at any ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield. Moreover, liquid separation operation is not essential in this reaction.

Moisture can be removed from the reaction mixture containing the compound represented by formula (Za-2) obtained above with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.

From the reaction mixture containing the compound represented by formula (Za-2) obtained above, the solvent can be distilled off under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (Za-2) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. with an appropriate solvent. It may be appropriately set according to the desired purity.

式中、Ｒｙａは、Ｃ１～Ｃ６のアルコキシ基を表し、Ｙａは、フェニル基、ピリジル基、ピリダジニル基、ピリミジニル基、ピラジニル基、トリアジニル基、テトラジニル基、チエニル基、チアゾリル基、イソチアゾリル基、またはチアジアゾリル基を表し、該フェニル基は、Ｒｙａがオルト位に置換した場合、さらにＲ５が適宜０～４置換し（ただし、２置換以上のＲ５がある場合、Ｒ５はそれぞれ独立した置換基を表す。）、Ｒ４がオルト位に位置した場合、さらにＲ５が適宜０～３置換し（ただし、２置換以上のＲ５がある場合、Ｒ５はそれぞれ独立した置換基を表す。）、該ピリジル基、該ピラジニル基、該ピリミジニル基、該ピリダジニル基、該トリアジニル基、または該テトラジニル基は、Ｒｙａがオルト位に置換した場合、さらにＲ５が適宜０～３置換し（ただし、２置換以上のＲ５がある場合、Ｒ５はそれぞれ独立した置換基を表す。）、Ｒ４がオルト位に位置した場合、さらにＲ５が適宜０～２置換し（ただし、２置換のＲ５がある場合、Ｒ５はそれぞれ独立した置換基を表す。）、該チエニル基、該チアゾリル基、該イソチアゾリル基、または該チアジアゾリル基は、Ｒｙａがオルト位に置換した場合、さらにＲ５が適宜０～２置換し（ただし、２置換以上のＲ５がある場合、Ｒ５はそれぞれ独立した置換基を表す。）、Ｒ４がオルト位に置換した場合、さらにＲ５が適宜０～１置換し、Ｒ１、Ｒ２、Ｒ７、およびＸは前記と同義である。[Manufacturing method C]

In the formula, Rya represents a C1-C6 alkoxy group, Ya is a phenyl group, pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, tetrazinyl group, thienyl group, thiazolyl group, isothiazolyl group, or thiadiazolyl When Rya is substituted at the ortho position, the phenyl group is optionally substituted with 0 to 4 R5 (provided that when there are two or more R5 substituted, each R5 represents an independent substituent.) , When R4 is located at the ortho position, R5 is optionally substituted with 0 to 3 (provided that when there are two or more R5, each R5 represents an independent substituent), the pyridyl group, the pyrazinyl group , the pyrimidinyl group, the pyridazinyl group, the triazinyl group, or the tetrazinyl group, when Rya is substituted at the ortho position, is further optionally substituted with 0 to 3 R5 (provided that when there are two or more R5 substituted, R5 each represent an independent substituent), and when R4 is located at the ortho position, R5 is optionally substituted with 0 to 2 substituents (provided that when there is a disubstituted R5, each R5 represents an independent substituent. ), the thienyl group, the thiazolyl group, the isothiazolyl group, or the thiadiazolyl group, when Rya is substituted at the ortho position, further optionally substituted with 0 to 2 R5 (provided that when there are 2 or more R5 substitutions, Each R5 represents an independent substituent.), when R4 is substituted at the ortho position, R5 is optionally substituted 0-1 times, and R1, R2, R7 and X are as defined above.

Production method C is a method for synthesizing a compound represented by formula (Za-4) having a hydroxyl group in Y among the compounds represented by formula (1), and represented by formula (Za-3) A production method comprising obtaining by reacting a compound and an acid in a solvent.

Acids used in this reaction include boron halides such as boron trichloride and boron tribromide.

The amount of the acid used in this reaction is not particularly limited as long as it is 1 equivalent or more relative to the compound represented by the formula (Za-3), as long as the intended reaction proceeds, but is preferred. is 1 equivalent or more and 10 equivalents or less.

The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds. , dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. These solvents can be used singly or as a mixture of two or more at any ratio.

The amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times the weight of the compound represented by the formula (Za-3). It is below.

The temperature for carrying out this reaction is not particularly limited as long as the desired reaction proceeds, but it is usually -80° C. or higher and 100° C. or lower, or the boiling point of the solvent or lower.

As a post-treatment of the reaction, a liquid separation operation can be performed by adding water or a suitable aqueous solution to the reaction mixture. When using an aqueous solution, use an acidic aqueous solution with hydrochloric acid, sulfuric acid, ammonium chloride, etc. dissolved, an alkaline aqueous solution with potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc. dissolved, or salt water. etc. can be used arbitrarily. During the liquid separation operation, if necessary, benzene solvents such as toluene, xylene, benzene, chlorobenzene, and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate, diethyl ether, diisopropyl ether, methyl- Ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane, which are incompatible with water. It is possible to add In addition, these solvents can be used alone, or two or more of them can be mixed at any ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield.

Moisture can be removed from the reaction mixture containing the compound represented by formula (Za-4) obtained above with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.

From the reaction mixture containing the compound represented by formula (Za-4) obtained above, the solvent can be distilled off under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (Za-4) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. with an appropriate solvent. It may be appropriately set according to the desired purity.

式中、Ｒｙｂは、置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ｃで適宜置換されてもよいＣ３～Ｃ６のアルキニル基、Ｃ３～Ｃ６のハロアルキニル基、置換基Ｄで適宜置換されてもよいアラルキル基、またはＲｘ１Ｃ（＝Ｏ）－を表し、Ｌｖは、メタンスルホニル基、トリフルオロメタンスルホニル基、ｐ‐トルエンスルホニル基、ハロゲン原子等の脱離基を表し、Ｒ１、Ｒ２、Ｒ７、Ｙａ、およびＸは前記と同義である。[Manufacturing method D]

In the formula, Ryb is a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with a substituent C, a substituent C2-C6 alkenyl group optionally substituted with C, C2-C6 haloalkenyl group, C3-C6 alkynyl group optionally substituted with substituent C, C3-C6 haloalkynyl group, substituent D represents an optionally substituted aralkyl group or Rx1C(=O)-, Lv represents a leaving group such as a methanesulfonyl group, a trifluoromethanesulfonyl group, a p-toluenesulfonyl group, a halogen atom, etc., and R1 , R2, R7, Ya, and X are as defined above.

Production method D comprises a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group, a C1 to C6 haloalkoxy group in which Ryb-O- may be optionally substituted with a substituent C, and a substituent C in the compound represented by the formula (1). A C3-C8 cycloalkoxy group optionally substituted with a C2-C6 alkenyloxy group optionally substituted with a substituent C, a C2-C6 haloalkenyloxy group optionally substituted with a substituent C a C3-C6 alkynyloxy group, a C3-C6 haloalkynyloxy group, an aralkyloxy group optionally substituted with a substituent D, or Rx1C(=O)O-(Rx1 is as defined above A method for synthesizing a compound represented by the formula (Za-5), which comprises reacting the compound represented by the formula (Za-4) with Ryb-Lv in the presence of a base in a solvent. It is a manufacturing method including

Ryb-Lv used in this reaction can be obtained as a commercial product or produced by a known method.

Ryb-Lv used in this reaction may be 1 equivalent or more relative to the compound represented by formula (Za-4), and is not particularly limited as long as the desired reaction proceeds, but is preferably is 1 equivalent or more and 10 equivalents or less.

Examples of bases used in this reaction include inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate and sodium hydride, and organic bases such as triethylamine, tributylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, collidine and lutidine. are exemplified, but are not particularly limited as long as the intended reaction proceeds.

The base used in this reaction may be 1 equivalent or more relative to the compound represented by formula (Za-4), and is not particularly limited as long as the target reaction proceeds, but preferably It is 1 equivalent or more and 10 equivalents or less.

The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane, alcohol solvents such as methanol, ethanol and isopropanol; benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene; ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate; nitrile solvents such as acetonitrile; Amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide and N,N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, dichloromethane, dichloroethane, chloroform, carbon tetrachloride halogen-based solvents such as dimethylsulfoxide, sulfur-based solvents such as sulfolane, ketone-based solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and the like. These solvents can be used singly or as a mixture of two or more at any ratio.

The amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times the weight of the compound represented by the formula (Za-4). It is below.

The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but it is usually from -20°C to 150°C or below the boiling point of the solvent.

As a post-treatment of the reaction, a liquid separation operation can be performed by adding water or a suitable aqueous solution to the reaction mixture. When using an aqueous solution, acidic aqueous solution with hydrochloric acid, sulfuric acid, ammonium chloride, etc. dissolved, alkaline aqueous solution with potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc. dissolved, thiosulfuric acid An aqueous solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved, a saline solution, or the like can be arbitrarily used. During the liquid separation operation, if necessary, benzene solvents such as toluene, xylene, benzene, chlorobenzene, and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate, diethyl ether, diisopropyl ether, methyl- Ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane, which are incompatible with water. It is possible to add In addition, these solvents can be used alone, or two or more of them can be mixed at any ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield.

The reaction mixture containing the compound represented by formula (Za-5) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.

From the reaction mixture containing the compound represented by formula (Za-5) obtained above, the solvent can be distilled off under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (Za-5) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. with an appropriate solvent. It may be appropriately set according to the desired purity.

式中、Ｒｙｃはハロゲン原子を表し、Ｙｃは、フェニル基、ピリジル基、ピリダジニル基、ピリミジニル基、ピラジニル基、トリアジニル基、テトラジニル基、チエニル基、チアゾリル基、イソチアゾリル基、またはチアジアゾリル基を表し、該フェニル基は、Ｒｙｃがオルト位に置換した場合、さらにＲ５が適宜０～４置換し（ただし、２置換以上のＲ５がある場合、Ｒ５はそれぞれ独立した置換基を表す。）、Ｒ４がオルト位に位置した場合、さらにＲ５が適宜０～３置換し（ただし、２置換以上のＲ５がある場合、Ｒ５はそれぞれ独立した置換基を表す。）、該ピリジル基、該ピラジニル基、該ピリミジニル基、該ピリダジニル基、該トリアジニル基、または該テトラジニル基は、Ｒｙｃがオルト位に置換した場合、さらにＲ５が適宜０～３置換し（ただし、２置換以上のＲ５がある場合、Ｒ５はそれぞれ独立した置換基を表す。）、Ｒ４がオルト位に位置した場合、さらにＲ５が適宜０～２置換し（ただし、２置換のＲ５がある場合、Ｒ５はそれぞれ独立した置換基を表す。）、該チエニル基、該チアゾリル基、該イソチアゾリル基、または該チアジアゾリル基は、Ｒｙｃがオルト位に置換した場合、さらにＲ５が適宜０～２置換し（ただし、２置換以上のＲ５がある場合、Ｒ５はそれぞれ独立した置換基を表す。）、Ｒ４がオルト位に置換した場合、さらにＲ５が適宜０～１置換し、Ｒｙｄは置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、またはＣ２～Ｃ６のハロアルケニル基、置換基Ｄで適宜置換されてもよいアリール基、または置換基Ｄで適宜置換されてもよいヘテロアリール基を表し、Ｒｙｄ－Ｂは有機ボロン酸類を表し、Ｒ１、Ｒ２、Ｒ７、およびＸは前記と同義である。[Manufacturing method E]

In the formula, Ryc represents a halogen atom, Yc represents a phenyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, a tetrazinyl group, a thienyl group, a thiazolyl group, an isothiazolyl group, or a thiadiazolyl group, In the phenyl group, when Ryc is substituted at the ortho position, R5 is optionally substituted with 0 to 4 (provided that when there are two or more R5 substituted, each R5 represents an independent substituent), and R4 is at the ortho position. , further optionally substituted with 0 to 3 R5 (provided that when there are two or more substituted R5, each R5 represents an independent substituent), the pyridyl group, the pyrazinyl group, the pyrimidinyl group, The pyridazinyl group, the triazinyl group, or the tetrazinyl group, when Ryc is substituted at the ortho position, is further optionally substituted with 0 to 3 R5 (provided that when there are two or more R5 substituted, each R5 is independently substituted). group), and when R4 is located at the ortho position, R5 is optionally substituted with 0 to 2 (provided that when there is disubstituted R5, each R5 represents an independent substituent.), the thienyl group , the thiazolyl group, the isothiazolyl group, or the thiadiazolyl group, when Ryc is substituted at the ortho position, further R5 is optionally substituted with 0 to 2 (provided that when there are 2 or more R5 substituted, each R5 is independently represents a substituent.), when R4 is substituted at the ortho position, R5 is optionally substituted 0 to 1 further, Ryd is a C1 to C6 alkyl group optionally substituted by a substituent C, C1 to C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with a substituent C, a C2-C6 alkenyl group optionally substituted with a substituent C, or a C2-C6 haloalkenyl group, a substituent D represents an aryl group which may be optionally substituted, or a heteroaryl group which may be optionally substituted with a substituent D, Ryd-B represents an organic boronic acid, and R1, R2, R7, and X are as defined above. .

In production method E, among the compounds represented by formula (1), Ryd is a C1 to C6 alkyl group optionally substituted with a substituent C, a C1 to C6 haloalkyl group optionally substituted with a substituent C, a C3-C8 cycloalkyl group optionally substituted with a substituent C, a C2-C6 alkenyl group optionally substituted with a substituent C, a C2-C6 haloalkenyl group, an aryl group optionally substituted with a substituent D, or A method for synthesizing a compound represented by the formula (Za-7), which is a heteroaryl group optionally substituted with a substituent D, comprising a compound represented by the formula (Za-6) and Ryd-B It is a production method including obtaining by Suzuki-Miyaura coupling in which organic boronic acids are reacted.

Preferred Ryc in the compound represented by formula (Za-6) is a chlorine atom, a bromine atom, or an iodine atom.

Ryd-B used in this reaction represents an organic boronic acid such as an organic boronic acid or an organic boronic acid ester, and can be obtained as a commercial product or produced by a known method.

The amount of Ryd-B used in this reaction is not particularly limited as long as it is 1 equivalent or more with respect to the compound represented by formula (Za-6), as long as the desired reaction proceeds. , preferably 1 equivalent or more and 10 equivalents or less.

The transition metals used in this reaction are palladium, nickel, ruthenium, etc., and may have ligands. Preferably, palladium acetate, [1,1′-bis(diphenylphosphino)ferrocene]palladium dichloride, tris(dibenzylideneacetone)dipalladium, tetrakis(triphenylphosphine)palladium, bis(triphenylphosphine)palladium dichloride and the like Palladium is mentioned.

The amount of the transition metal used in this reaction is 0.001 equivalent or more and 1 equivalent or less with respect to the compound represented by formula (Za-6), but is not particularly limited as long as the desired reaction proceeds. never

A phosphine ligand such as triphenylphosphine or tricyclohexylphosphine can be added for efficient progress of this reaction.

The amount of the phosphine ligand used in this reaction is 0.001 equivalent or more and 1 equivalent or less with respect to the compound represented by formula (Za-6), but is particularly limited as long as the desired reaction proceeds. will not be

The base used in this reaction includes inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate and tripotassium phosphate, and metal alkoxides such as sodium methoxide, sodium ethoxide and potassium t-butoxide.

The amount of the base used in this reaction is not particularly limited as long as it is 1 equivalent or more with respect to the compound represented by formula (Za-6) as long as the target reaction proceeds, but preferably , 1 equivalent or more and 50 equivalents or less.

The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds. and benzene-based solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene. These solvents can be used singly or as a mixture of two or more at any ratio.

The amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times the weight of the compound represented by the formula (Za-6). It is below.

The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually from 30° C. to 200° C. or below the boiling point of the solvent.

As a post-treatment of the reaction, a liquid separation operation can be performed by adding water or a suitable aqueous solution to the reaction mixture. When using an aqueous solution, acidic aqueous solution with hydrochloric acid, sulfuric acid, ammonium chloride, etc. dissolved, alkaline aqueous solution with potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc. dissolved, thiosulfuric acid An aqueous solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved, a saline solution, or the like can be arbitrarily used. During the liquid separation operation, if necessary, benzene solvents such as toluene, xylene, benzene, chlorobenzene, and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate, diethyl ether, diisopropyl ether, methyl- Ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane, which are incompatible with water. It is possible to add In addition, these solvents can be used alone, or two or more of them can be mixed at any ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield. In addition, although it is possible to remove insoluble matter by performing a filtering operation, it is not essential.
The reaction mixture containing the compound represented by formula (Za-7) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.

From the reaction mixture containing the compound represented by formula (Za-7) obtained above, the solvent can be distilled off under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (Za-7) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. with an appropriate solvent. It may be appropriately set according to the desired purity.

式中、Ｒｙｅは置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、またはＣ２～Ｃ６のハロアルキニル基を表し、Ｒ１、Ｒ２、Ｒ７、Ｒｙｃ、ＸおよびＹｃは前記と同義である。[Manufacturing method F]

In the formula, Rye represents a C2-C6 alkynyl group optionally substituted with a substituent C or a C2-C6 haloalkynyl group, and R1, R2, R7, Ryc, X and Yc are as defined above. .

In the production method F, among the compounds represented by the formula (1), Rye is a C2-C6 alkynyl group optionally substituted with a substituent C or a C2-C6 haloalkynyl group of the formula (Za- A method for synthesizing the compound represented by 8), wherein the compound represented by (Za-6) and a terminal alkyne compound are reacted in a solvent in the presence of transition metals and a base by Sonogashira coupling. It is a manufacturing method including obtaining.

Preferred Ryc in the compound represented by formula (Za-6) is a chlorine atom, a bromine atom, or an iodine atom.

The terminal alkyne compound used in this reaction can be obtained as a commercial product or produced by a known method. Trimethylsilylacetylene can also be used as the terminal alkyne compound. In this case, it is necessary to introduce a trimethylsilylethynyl group into the compound represented by the formula (Za-6) and then desilylate it. For desilylation, see Journal of the American Chemical Society, Vol. 131, No. 2, pp. 634-643 (2009). and Journal of Organometallic Chemistry, Vol. 696, No. 25, pp. 4039-4045 (2011). It can be performed with reference to non-patent literature such as.

The amount of the terminal alkyne compound used in this reaction is not particularly limited as long as it is 1 equivalent or more with respect to the compound represented by formula (Za-6), as long as the desired reaction proceeds. Preferably, it is 1 equivalent or more and 10 equivalents or less.

The transition metals used in this reaction may have a ligand, palladium acetate, [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride, tris(dibenzylideneacetone) dipalladium, tetrakis ( and palladium compounds such as triphenylphosphine)palladium and bis(triphenylphosphine)palladium dichloride. Coppers such as copper chloride, copper bromide and copper iodide are also used at the same time.

The amount of transition metals used in this reaction may be 0.001 equivalents or more of palladium compounds and copper compounds relative to the compound represented by formula (Za-6), respectively, and the desired reaction proceeds. There are no particular restrictions as long as it does. Preferred amounts for both are 0.001 equivalent or more and 1 equivalent or less.

The base used in this reaction includes organic amines such as triethylamine, tributylamine, isopropylamine, diethylamine, diisopropylamine and diisopropylethylamine, and inorganic bases such as sodium carbonate, potassium carbonate and cesium carbonate.

The amount of the base used in this reaction is not particularly limited as long as it is 1 equivalent or more with respect to the compound represented by formula (Za-6) as long as the target reaction proceeds, but preferably , 1 equivalent or more and 50 equivalents or less. In addition, organic bases in liquid form can be used as solvents.

A phosphine ligand such as tri-t-butylphosphine, 2-dicyclohexylphosphino-2'4'6'-triisopropylbiphenyl, etc. can be added in order to allow the reaction to proceed efficiently, but is not essential. .

The amount of the phosphine ligand used in this reaction is 0.001 equivalent or more and 1 equivalent or less with respect to the compound represented by formula (Za-6), but is particularly limited as long as the desired reaction proceeds. will not be

The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane, Benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene Ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate Nitrile solvents such as acetonitrile, N-methylpyrrolidone, N,N-dimethylformamide , N,N-dimethylacetamide and other amide solvents, 1,3-dimethyl-2-imidazolidinone and other urea solvents, dichloromethane, dichloroethane, chloroform, carbon tetrachloride and other halogen solvents, triethylamine, tributylamine, Examples include organic amine solvents such as isopropylamine, diethylamine, diisopropylamine, and diisopropylethylamine. These solvents can be used singly or as a mixture of two or more at any ratio.

The amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times the weight of the compound represented by the formula (Za-6). It is below.

The temperature for carrying out this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 0° C. or higher and 150° C. or lower or the boiling point of the solvent or lower.

As a post-treatment of the reaction, a liquid separation operation can be performed by adding water or a suitable aqueous solution to the reaction mixture. When using an aqueous solution, an acidic aqueous solution with hydrochloric acid, sulfuric acid, etc. dissolved, an alkaline aqueous solution with potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc. dissolved, sodium thiosulfate, sulfurous acid An aqueous solution in which a salt containing a sulfur atom such as sodium is dissolved, a saline solution, or the like can be arbitrarily used. During the liquid separation operation, if necessary, benzene solvents such as toluene, xylene, benzene, chlorobenzene, and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate, diethyl ether, diisopropyl ether, methyl- Ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane, which are incompatible with water. It is possible to add Moreover, these solvents can be used alone, or two or more of them can be mixed at any ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield. In addition, although it is possible to remove insoluble matter by performing a filtering operation, it is not essential.

The reaction mixture containing the compound represented by formula (Za-8) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.

From the reaction mixture containing the compound represented by formula (Za-8) obtained above, the solvent can be distilled off under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (Za-8) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. with an appropriate solvent. It may be appropriately set according to the desired purity.

式中、Ｒｙｇは、置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニルオキシ基、Ｃ２～Ｃ６のハロアルケニルオキシ基、置換基Ｃで適宜置換されてもよいＣ３～Ｃ６のアルキニルオキシ基、Ｃ３～Ｃ６のハロアルキニルオキシ基、置換基Ｄで適宜置換されてもよいヘテロアリール基、置換基Ｄで適宜置換されてもよいアラルキルオキシ基、ＲａＲｂＮ－（ここでＲａおよびＲｂは前記と同義である）、Ｒｃ－Ｌ－（ここで、ＲｃおよびＬは前記と同義である。）、またはＲｘ４Ｒｘ５Ｃ＝Ｎ－Ｏ－（ここで、Ｒｘ４およびＲｘ５は、それぞれ独立していて、水素原子、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、またはＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）を表す。）を表し、Ｑは、水素原子または金属を表し、Ｒ１、Ｒ２、Ｒ７、Ｒｙｃ、Ｘ、およびＹｃは前記と同義である。[Manufacturing method G]

In the formula, Ryg is a C1-C6 alkoxy group optionally substituted with a substituent C, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group optionally substituted with a substituent C, substituted C2-C6 alkenyloxy group optionally substituted by group C, C2-C6 haloalkenyloxy group, C3-C6 alkynyloxy group optionally substituted by substituent C, C3-C6 haloalkynyl an oxy group, a heteroaryl group optionally substituted with a substituent D, an aralkyloxy group optionally substituted with a substituent D, RaRbN- (where Ra and Rb are as defined above), Rc-L - (wherein Rc and L are as defined above), or Rx4Rx5C=NO- (wherein Rx4 and Rx5 are each independently substituted with a hydrogen atom, a substituent B C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group, or RaRbN- (Here, Ra and Rb are as defined above.), Q represents a hydrogen atom or a metal, R1, R2, R7, Ryc, X, and Yc are as defined above. be.

In production method G, Ryg is a C1-C6 alkoxy group optionally substituted with a substituent C, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group optionally substituted with a substituent C, C2-C6 alkenyloxy group optionally substituted with substituent C, C2-C6 haloalkenyloxy group, C3-C6 alkynyloxy group optionally substituted with substituent C, C3-C6 halo an alkynyloxy group, a heteroaryl group optionally substituted with a substituent D, an aralkyloxy group optionally substituted with a substituent D, RaRbN- (wherein Ra and Rb are as defined above), Rc- L- (wherein Rc and L are as defined above), or Rx4Rx5C=NO- (wherein Rx4 and Rx5 are as defined above) represented by formula (Za-9) A production method comprising reacting a compound represented by formula (Za-6) with Ryg-Q in the presence of a base in a solvent.

Preferred Ryc in the compound represented by formula (Za-6) is a fluorine atom, a chlorine atom, or a bromine atom.

Ryg-Q used in this reaction is commercially available or can be produced by a known method. Preferred Q is a hydrogen atom or alkali metals such as sodium and potassium.

The amount of Ryg-Q used in this reaction is not particularly limited as long as it is 1 equivalent or more relative to the compound represented by formula (Za-6), as long as the desired reaction proceeds. , usually 1 equivalent or more and 30 equivalents or less. Moreover, when Q represents a hydrogen atom, it can be used as a solvent.

The base used in this reaction is preferably inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate and sodium hydride. Also, when Q is an alkali metal, the use of a base is not essential.

The amount of the base used in this reaction is not particularly limited as long as it is 1 equivalent or more relative to the compound represented by formula (Za-6), as long as the target reaction proceeds. It is 1 equivalent or more and 30 equivalents or less.

The solvent used in this reaction is not particularly limited as long as the intended reaction proceeds, but an alcoholic solvent represented by Ryg-H (wherein Ryg is as defined above), Ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane; benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene; ethyl acetate, isopropyl acetate, and butyl acetate; ester solvents such as acetonitrile, nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, 1,3-dimethyl-2-imidazolidinone and the like Examples include urea-based solvents, halogen-based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, sulfur-based solvents such as dimethylsulfoxide and sulfolane, and ketone-based solvents such as acetone, methyl ethyl ketone and methyl isobutyl ketone. These solvents can be used singly or as a mixture of two or more at any ratio.

The amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times the weight of the compound represented by the formula (Za-6). It is below.

The temperature for carrying out this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 0° C. or higher and 150° C. or lower or the boiling point of the solvent or lower.

As a post-treatment of the reaction, a liquid separation operation can be performed by adding water or a suitable aqueous solution to the reaction mixture. When using an aqueous solution, acidic aqueous solution with hydrochloric acid, sulfuric acid, ammonium chloride, etc. dissolved, alkaline aqueous solution with potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc. dissolved, thiosulfuric acid An aqueous solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved, a saline solution, or the like can be arbitrarily used. During the liquid separation operation, if necessary, benzene solvents such as toluene, xylene, benzene, chlorobenzene, and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate, diethyl ether, diisopropyl ether, methyl- Ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane, which are incompatible with water. It is possible to add In addition, these solvents can be used alone, or two or more of them can be mixed at any ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield.

Moisture can be removed from the reaction mixture containing the compound represented by formula (Za-9) obtained above with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.

From the reaction mixture containing the compound represented by formula (Za-9) obtained above, the solvent can be distilled off under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (Za-9) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. with an appropriate solvent. It may be appropriately set according to the desired purity.

式中、Ｒ２ａは、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、フェニル基、５員～６員の複素環基、または８～１０員の複素環基を表し、該フェニル基は、Ｒｙａが適宜１～５置換した場合、さらにＲ３が適宜０～４置換し（ただし、２置換以上のＲ３がある場合、Ｒ３はそれぞれ独立した置換基を表す。）、該５～６員の複素環基、または該８～１０員の複素環基は、Ｒｙａが適宜１～６置換した場合、Ｒ３が適宜０～５置換し（ただし、２置換以上のＲ３がある場合、Ｒ３はそれぞれ独立した置換基を表す。）、Ｒ１、Ｒ７、Ｒｙａ、ＸおよびＹは前記と同義である。[Manufacturing method H]

In the formula, R2a is a C1-C6 alkyl group optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with a substituent A, a substituent C1-C6 alkoxy group optionally substituted with A, C1-C6 haloalkoxy group optionally substituted with substituent A, C3-C8 cycloalkoxy group optionally substituted with substituent A, phenyl group, 5- to 6-membered represents a heterocyclic group or an 8- to 10-membered heterocyclic group, wherein the phenyl group is optionally substituted with 1 to 5 Rya and further optionally substituted with 0 to 4 R3 (provided that there are 2 or more R3 substituted R3 represents an independent substituent.), the 5- to 6-membered heterocyclic group, or the 8- to 10-membered heterocyclic group is optionally substituted with 1 to 6 Rya, and R3 is optionally 0 ~5 substituted (provided that when there are two or more R3 substituted, each R3 represents an independent substituent), and R1, R7, Rya, X and Y are as defined above.

Production method H is a method for synthesizing a compound represented by formula (Za-11) having a hydroxyl group at R2a among the compounds represented by formula (1), and represented by formula (Za-10) A production method comprising obtaining by reacting a compound and an acid in a solvent.

Production method H can be carried out according to production method C by using the compound represented by formula (Za-3) in production method C in place of the compound represented by formula (Za-10). can.

式中、Ｒ１、Ｒ２ａ、Ｒｙｂ、Ｒ７、Ｘ、ＹおよびＬｖは前記と同義である。[Manufacturing method I]

In the formula, R1, R2a, Ryb, R7, X, Y and Lv are as defined above.

In the production method I, among the compounds represented by the formula (1), Ryb-O- may be optionally substituted with a substituent C, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a substituent C A C3-C8 cycloalkoxy group optionally substituted with a C2-C6 alkenyloxy group optionally substituted with a substituent C, a C2-C6 haloalkenyloxy group optionally substituted with a substituent C a C3-C6 alkynyloxy group, a C3-C6 haloalkynyloxy group, an aralkyloxy group optionally substituted with a substituent D, or Rx1C(=O)O-(Rx1 is as defined above .) is a method for synthesizing a compound represented by the formula (Za-12), wherein the compound represented by the formula (Za-11) and Ryb-Lv are reacted in a solvent in the presence of a base. It is a manufacturing method including

Production method I can be carried out according to production method D by using the compound represented by formula (Za-4) in production method D in place of the compound represented by formula (Za-11). can.

式中、Ｒ２ｃはフェニル基、５員～６員の複素環基、または８～１０員の複素環基を表し、該フェニル基は、Ｒｙｃが適宜１～５置換した場合、さらにＲ３が適宜０～４置換し（ただし、２置換以上のＲ３がある場合、Ｒ３はそれぞれ独立した置換基を表す。）、該５～６員の複素環基、または該８～１０員の複素環基は、Ｒｙｃが適宜１～６置換した場合、Ｒ３が適宜０～５置換し（ただし、２置換以上のＲ３がある場合、Ｒ３はそれぞれ独立した置換基を表す。）、Ｒｙｄ－Ｂは有機ボロン酸類を表し、Ｒ１、Ｒｙｃ、Ｒｙｄ、Ｒ７、Ｘ、およびＹは前記と同義である。[Manufacturing method J]

In the formula, R2c represents a phenyl group, a 5- to 6-membered heterocyclic group, or an 8- to 10-membered heterocyclic group. ~4-substituted (provided that when there are two or more R3 substituted, each R3 represents an independent substituent), the 5- to 6-membered heterocyclic group or the 8- to 10-membered heterocyclic group, When Ryc is optionally substituted 1 to 6, R3 is optionally substituted 0 to 5 (however, when there are two or more substituted R3, each R3 represents an independent substituent.), and Ryd-B is an organic boronic acid. and R1, Ryc, Ryd, R7, X, and Y are as defined above.

In production method J, among the compounds represented by formula (1), Ryd is a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group optionally substituted with a substituent C, a C3-C8 cycloalkyl group optionally substituted with a substituent C, a C2-C6 alkenyl group optionally substituted with a substituent C, a C2-C6 haloalkenyl group, an aryl group optionally substituted with a substituent D, or A method for synthesizing a compound represented by the formula (Za-14), which is a heteroaryl group optionally substituted with a substituent D, comprising a compound represented by the formula (Za-13) and Ryd-B It is a production method including obtaining by Suzuki-Miyaura coupling in which organic boronic acids are reacted.

Preferred Ryc in the compound represented by formula (Za-13) is a chlorine atom, a bromine atom, or an iodine atom.

Ryd-B used in this reaction represents an organic boronic acid such as an organic boronic acid or an organic boronic acid ester, and can be obtained as a commercial product or produced by a known method.

By using the compound represented by Formula (Za-6) in Production Method E in place of the compound represented by Formula (Za-13), Production Method J can be carried out according to Production Method E. can.

式中、Ｒ１、Ｒ２ｃ、Ｒ７、Ｒｙｃ、Ｒｙｅ、ＸおよびＹは前記と同義である。[Manufacturing method K]

In the formula, R1, R2c, R7, Ryc, Rye, X and Y are as defined above.

In the production method K, among the compounds represented by the formula (1), Rye is a C2-C6 alkynyl group optionally substituted with a substituent C or a C2-C6 haloalkynyl group of the formula (Za- 15) A method for synthesizing the compound represented by (Za-13), wherein the compound represented by (Za-13) and a terminal alkyne compound are reacted in the presence of transition metals and a base in a solvent by Sonogashira coupling. It is a manufacturing method including

In formula (Za-13), Ryc is preferably a chlorine atom, a bromine atom, or an iodine atom.

The terminal alkyne compound used in this reaction can be obtained as a commercial product or produced by a known method. Trimethylsilylacetylene can also be used as the terminal alkyne compound. In this case, it is necessary to introduce a trimethylsilylethynyl group into the compound represented by the formula (Za-13) and then desilylate it. For desilylation, see Journal of the American Chemical Society, Vol. 131, No. 2, pp. 634-643 (2009). and Journal of Organometallic Chemistry, Vol. 696, No. 25, pp. 4039-4045 (2011). Non-Patent Literature, etc. can be referred to.

By using the compound represented by the formula (Za-6) in the production method F in place of the compound represented by the formula (Za-13), the production method K can be carried out according to the production method F. can.

式中、Ｒｙｆはハロゲン原子を表し、Ｒ２ｂは、フェニル基、５員～６員の複素環基、または８～１０員の複素環基を表し、該フェニル基は、Ｒ３が適宜０～４置換し（ただし、２置換以上のＲ３がある場合、Ｒ３はそれぞれ独立した置換基を表す。）、該５～６員の複素環基、または該８～１０員の複素環基は、Ｒ３が適宜０～５置換し（ただし、２置換以上のＲ３がある場合、Ｒ３はそれぞれ独立した置換基を表す。）、ＨａｌＲはハロゲン化剤を表し、Ｒ１、Ｒ７、Ｘ、およびＹは前記と同義である。[Manufacturing method L]

In the formula, Ryf represents a halogen atom; R2b represents a phenyl group, a 5- to 6-membered heterocyclic group, or an 8- to 10-membered heterocyclic group; (However, when there are two or more substituted R3, each R3 represents an independent substituent.) The 5- to 6-membered heterocyclic group or the 8- to 10-membered heterocyclic group is optionally represented by R3 0 to 5 substituted (provided that when there are two or more R3 substituted, each R3 represents an independent substituent), HalR represents a halogenating agent, and R1, R7, X, and Y are as defined above. be.

Production method L is a production method for obtaining a compound represented by formula (Za-17), in which Ryf is a halogen atom, among the compounds represented by formula (1). A compound and a halogenating agent (HalR) are reacted in a solvent, or a compound represented by the formula (Za-16) and a halogenating agent (HalR), and a radical initiator are reacted in a solvent. It is a manufacturing method that also includes making
In this reaction, a base or radical initiator can be added. The conditions may be appropriately set so that the intended reaction proceeds.

A method of reacting the compound represented by the formula (Za-16) with a halogenating agent (HalR) in a solvent is described below.

Halogenating agents used in this reaction include selectrofluor (N-fluoro-N'-triethylenediamine bis(tetrafluoroborate)), N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, 1 ,3-dichloro-5,5-dimethylhydantoin, 1,3-dibromo-5,5-dimethylhydantoin, 1,3-diiodo-5,5-dimethylhydantoin, bromine, iodine and the like.

The amount of the halogenating agent used in this reaction is not particularly limited as long as it is 1 equivalent or more relative to the compound represented by formula (Za-16), as long as the target reaction proceeds. Preferably, it is 1 equivalent or more and 10 equivalents or less. However, the amount of the halogenating agent containing hydantoin is not particularly limited as long as it is 0.5 equivalents or more as long as the intended reaction proceeds, and is preferably 1 equivalent or more and 5 equivalents or less.

When the halogenating agent used in this reaction is an iodinating agent, an acid such as an inorganic acid such as hydrochloric acid or sulfuric acid, or an organic acid such as acetic acid, trifluoroacetic acid, methanesulfonic acid or trifluoromethanesulfonic acid may be added. can be done.

When the halogenating agent used in this reaction is an iodinating agent, the amount of the acid used is 0.01 equivalent or more with respect to the compound represented by the formula (Za-16). Although it is not particularly limited as long as it proceeds, it is preferably 0.1 equivalent or more and 3 equivalent or less.

The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds. , diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, and other ether solvents; methanol, ethanol, isopropanol, and other alcohol solvents; benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, and other benzene solvents. , ethyl acetate, isopropyl acetate, ester solvents such as butyl acetate, nitrile solvents such as acetonitrile, N-methylpyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide and other amide solvents, 1,3- Urea-based solvents such as dimethyl-2-imidazolidinone, halogen-based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride can be used. These solvents can be used singly or as a mixture of two or more at any ratio.

The amount of the solvent used in this reaction is not particularly limited as long as the intended reaction proceeds, but is usually 3 to 200 times the weight of the compound represented by the formula (Za-16). It is below.

The temperature for carrying out this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 0° C. or higher and 150° C. or lower or the boiling point of the solvent or lower.

As a post-treatment of the reaction, a liquid separation operation can be performed by adding water or a suitable aqueous solution to the reaction mixture. When using an aqueous solution, acidic aqueous solution with hydrochloric acid, sulfuric acid, ammonium chloride, etc. dissolved, alkaline aqueous solution with potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc. dissolved, thiosulfuric acid An aqueous solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved, a saline solution, or the like can be arbitrarily used. During the liquid separation operation, if necessary, benzene solvents such as toluene, xylene, benzene, chlorobenzene, and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate, diethyl ether, diisopropyl ether, methyl- Ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane, which are incompatible with water. It is possible to add In addition, these solvents can be used alone, or two or more of them can be mixed at any ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield.

Moisture can be removed from the reaction mixture containing the compound represented by formula (Za-17) obtained above with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.

From the reaction mixture containing the compound represented by formula (Za-17) obtained above, the solvent can be distilled off under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (Za-17) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. with an appropriate solvent. It may be appropriately set according to the desired purity.

A method of reacting the compound represented by formula (Za-16), the halogenating agent (HalR), and the radical initiator in a solvent is described below.

Radical initiators used in this reaction include azobisisobutyronitrile, benzoyl peroxide and the like.

The amount of the radical initiator used in this reaction is not particularly limited as long as the intended reaction proceeds, but usually 0.01 equivalent with respect to the compound represented by the formula (Za-16) It is more than 1.0 equivalent or less.

Halogenating agents used in this reaction include N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, 1,3-dichloro-5,5-dimethylhydantoin, and 1,3-dibromo-5,5-dimethylhydantoin. , 1,3-diiodo-5,5-dimethylhydantoin and the like.

The amount of the halogenating agent used in this reaction is not particularly limited as long as it is 1 equivalent or more with respect to the compound represented by formula (Za-16), as long as the desired reaction proceeds. Usually, it is 1 equivalent or more and 1.8 equivalents or less.

The solvent used in this reaction is not particularly limited as long as the intended reaction proceeds, but halogenated benzene solvents such as chlorobenzene and dichlorobenzene; Solvents include halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane. These solvents can be used singly or as a mixture of two or more at any ratio.

The amount of the solvent used in this reaction is not particularly limited as long as the intended reaction proceeds, but is usually 3 to 200 times the weight of the compound represented by the formula (Za-16). It is below.

The temperature for carrying out this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 20° C. or higher and 150° C. or lower, or the boiling point of the solvent or lower.

As a post-treatment of the reaction, a liquid separation operation can be performed by adding water or a suitable aqueous solution to the reaction mixture. When using an aqueous solution, acidic aqueous solution with hydrochloric acid, sulfuric acid, ammonium chloride, etc. dissolved, alkaline aqueous solution with potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc. dissolved, thiosulfuric acid An aqueous solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved, a saline solution, or the like can be arbitrarily used. During the liquid separation operation, if necessary, benzene solvents such as toluene, xylene, benzene, chlorobenzene, and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate, diethyl ether, diisopropyl ether, methyl- Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, and chloroform, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane, may be added. It is possible. In addition, these solvents can be used alone, or two or more of them can be mixed at any ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield.

Moisture can be removed from the reaction mixture containing the compound represented by formula (Za-17) obtained above with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.

From the reaction mixture containing the compound represented by formula (Za-17) obtained above, the solvent can be distilled off under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (Za-17) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. with an appropriate solvent. It may be appropriately set according to the desired purity.

式中、Ｒ６は、水素原子、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、またはＲｃ－Ｌ－（ここで、ＲｃおよびＬは前記と同義である。）を表し、
Ｌｖはメタンスルホニル基、トリフルオロメタンスルホニル基、ｐ‐トルエンスルホニル基、ハロゲン原子等の脱離基を表し、Ｒ１、Ｒ２、ＸおよびＹは、前記と同義である。[Manufacturing method M]

In the formula, R6 is a hydrogen atom, a halogen atom, a C1-C6 alkyl group optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 optionally substituted with a substituent A a cycloalkyl group, a C2-C6 alkenyl group optionally substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group optionally substituted with a substituent A, a C2-C6 a haloalkynyl group, a C1-C6 alkoxy group optionally substituted with a substituent A, a C1-C6 haloalkoxy group, or Rc-L- (wherein Rc and L are as defined above); represent,
Lv represents a leaving group such as a methanesulfonyl group, a trifluoromethanesulfonyl group, a p-toluenesulfonyl group and a halogen atom, and R1, R2, X and Y are as defined above.

Production method M is a method for obtaining a compound represented by formula (Zb-2) among compounds represented by formula (1), wherein a production intermediate represented by formula (Zb-1) and R1 -Lv in a solvent in the presence of a base.
The compound represented by formula (Zb-1) used in this reaction can be obtained according to the synthesis method described in Production Method AB.

R1-Lv used in this reaction can be obtained as a commercial product or produced by a known method.

The amount of R1-Lv used in this reaction may be 1 equivalent or more with respect to the compound represented by formula (Zb-1), and is not particularly limited as long as the desired reaction proceeds. , preferably 1 equivalent or more and 10 equivalents or less.

Examples of the base used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, and sodium hydride. will not be

The amount of the base used in this reaction is not particularly limited as long as it is 1 equivalent or more with respect to the compound represented by the formula (Zb-1), as long as the intended reaction proceeds, but is preferred. is 1 equivalent or more and 10 equivalents or less.

The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane, alcohol solvents such as methanol, ethanol and isopropanol; benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene; ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate; nitrile solvents such as acetonitrile; Amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide and N,N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, dichloromethane, dichloroethane, chloroform, carbon tetrachloride halogen-based solvents such as dimethylsulfoxide, sulfur-based solvents such as sulfolane, ketone-based solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and the like. These solvents can be used singly or as a mixture of two or more at any ratio.

The amount of the solvent used in this reaction is not particularly limited as long as the intended reaction proceeds, but is usually 3 to 200 times the weight of the compound represented by the formula (Zb-1). It is below.

The temperature for carrying out this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 0° C. or higher and 150° C. or lower or the boiling point of the solvent or lower.
As a post-treatment of the reaction, a liquid separation operation can be performed by adding water or a suitable aqueous solution to the reaction mixture. When using an aqueous solution, acidic aqueous solution with hydrochloric acid, sulfuric acid, ammonium chloride, etc. dissolved, alkaline aqueous solution with potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc. dissolved, thiosulfuric acid An aqueous solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved, a saline solution, or the like can be arbitrarily used. During the liquid separation operation, if necessary, benzene solvents such as toluene, xylene, benzene, chlorobenzene, and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate, diethyl ether, diisopropyl ether, methyl- Ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane, which are incompatible with water. It is possible to add In addition, these solvents can be used alone, or two or more of them can be mixed at any ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield.

The reaction mixture containing the compound represented by formula (Zb-2) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.

From the reaction mixture containing the compound represented by formula (Zb-2) obtained above, the solvent can be distilled off under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (Zb-2) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. with an appropriate solvent. It may be appropriately set according to the desired purity.

式中、ＳＲは硫黄化剤を表し、Ｒ１、Ｒ２、Ｒ６、およびＹは、前記と同義である。[Manufacturing method N]

In the formula, SR represents a sulfurizing agent, and R1, R2, R6 and Y are as defined above.

Production method N is a production method for obtaining a compound represented by formula (Zb-4) among the compounds represented by formula (1), wherein the compound represented by formula (Zb-3) and sulfuration agent (SR) in a solvent.

Sulfurizing agents used in this reaction include Lawesson's reagent (2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide) and the like.

The amount of the sulfurizing agent used in this reaction may be 0.5 equivalents or more with respect to the compound represented by formula (Zb-3), and is not particularly limited as long as the desired reaction proceeds. However, it is preferably from 1 equivalent to 10 equivalents.

The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane, Benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, and the like are included. These solvents can be used singly or as a mixture of two or more at any ratio.

The amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times the weight of the compound represented by the formula (Zb-3). It is below.

The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually from 50° C. to 180° C. or below the boiling point of the solvent.

As a post-treatment of the reaction, a liquid separation operation can be performed by adding water or a suitable aqueous solution to the reaction mixture. When using an aqueous solution, use an acidic aqueous solution with hydrochloric acid, sulfuric acid, ammonium chloride, etc. dissolved, an alkaline aqueous solution with potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc. dissolved, or salt water. etc. can be used arbitrarily. During the liquid separation operation, if necessary, benzene solvents such as toluene, xylene, benzene, chlorobenzene, and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate, diethyl ether, diisopropyl ether, methyl- Ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane, which are incompatible with water. It is possible to add In addition, these solvents can be used alone, or two or more of them can be mixed at any ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield. Moreover, liquid separation operation is not essential in this reaction.

Moisture can be removed from the reaction mixture containing the compound represented by formula (Zb-4) obtained above with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.

From the reaction mixture containing the compound represented by formula (Zb-4) obtained above, the solvent can be distilled off under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (Zb-4) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. with an appropriate solvent. It may be appropriately set according to the desired purity.

式中、Ｒ１、Ｒ２、Ｙａ、Ｒｙａ、Ｒ６、およびＸは前記と同義である。[Manufacturing method O]

In the formula, R1, R2, Ya, Rya, R6 and X are as defined above.

Production method O is a method for synthesizing a compound represented by formula (Zb-6) having a hydroxyl group in Y among the compounds represented by formula (1), and represented by formula (Zb-5) A production method comprising obtaining by reacting a compound and an acid in a solvent.

Acids used in this reaction include boron halides such as boron trichloride and boron tribromide.

Production method O can be carried out according to production method C by using the compound represented by formula (Za-3) in production method C in place of the compound represented by formula (Zb-5). can.

式中、Ｒ１、Ｒ２、Ｙａ、Ｒｙｂ、Ｒ６、ＸおよびＬｖは前記と同義である。[Manufacturing method P]

In the formula, R1, R2, Ya, Ryb, R6, X and Lv are as defined above.

Production method P is a method for synthesizing the compound represented by formula (Zb-7) among the compounds represented by formula (1), wherein the compound represented by formula (Zb-6) and Ryb-Lv and in a solvent in the presence of a base.

Ryb-Lv used in this reaction can be obtained as a commercial product or produced by a known method.

Production method P can be carried out according to production method D by using the compound represented by formula (Za-4) in production method D in place of the compound represented by formula (Zb-6). can.

式中、Ｒｙｄ－Ｂは有機ボロン酸類を表し、Ｒ１、Ｒ２、Ｙｃ、Ｒｙｃ、Ｒｙｄ、Ｒ６およびＸは前記と同義である。[Manufacturing method Q]

In the formula, Ryd-B represents an organic boronic acid, and R1, R2, Yc, Ryc, Ryd, R6 and X are as defined above.

In production method Q, among the compounds represented by formula (1), Ryd is a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group optionally substituted with a substituent C, a C3-C8 cycloalkyl group optionally substituted with a substituent C, a C2-C6 alkenyl group optionally substituted with a substituent C, a C2-C6 haloalkenyl group, an aryl group optionally substituted with a substituent D, or A method for synthesizing a compound represented by the formula (Zb-9), which is a heteroaryl group optionally substituted with a substituent D, comprising a compound represented by the formula (Zb-8) and a compound represented by Ryd-B It is a production method including obtaining by Suzuki-Miyaura coupling in which organic boronic acids are reacted.

Preferred Ryc in the compound represented by formula (Zb-8) is a chlorine atom, a bromine atom, or an iodine atom.

Ryd-B used in this reaction represents an organic boronic acid such as an organic boronic acid or an organic boronic acid ester, and can be obtained as a commercial product or produced by a known method.

Production method Q can be carried out according to production method E by using the compound represented by formula (Za-6) in production method E in place of the compound represented by formula (Zb-8). can.

式中、Ｒｙｅは置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、またはＣ２～Ｃ６のハロアルキニル基を表し、Ｒ１、Ｒ２、Ｙｃ、Ｒｙｃ、Ｒ６およびＸは前記と同義である。[Manufacturing method R]

In the formula, Rye represents a C2-C6 alkynyl group optionally substituted with a substituent C or a C2-C6 haloalkynyl group, and R1, R2, Yc, Ryc, R6 and X are as defined above. .

In the production method R, among the compounds represented by the formula (1), Rye is a C2-C6 alkynyl group optionally substituted with a substituent C or a C2-C6 haloalkynyl group of the formula (Zb- 10) A method for synthesizing the compound represented by (Zb-8), wherein the compound represented by (Zb-8) and a terminal alkyne compound are reacted in the presence of transition metals and a base in a solvent to obtain by Sonogashira coupling. It is a manufacturing method including

In formula (Zb-8), Ryc is preferably a chlorine atom, a bromine atom, or an iodine atom.

The terminal alkyne compound used in this reaction can be obtained as a commercial product or produced by a known method. Trimethylsilylacetylene can also be used as the terminal alkyne compound. In this case, it is necessary to introduce a trimethylsilylethynyl group into the compound represented by the formula (Zb-8) and then desilylate it. For desilylation, see Journal of the American Chemical Society, Vol. 131, No. 2, pp. 634-643 (2009). and Journal of Organometallic Chemistry, Vol. 696, No. 25, pp. 4039-4045 (2011). It can be performed with reference to non-patent literature such as.

Carrying out Production Method R according to Production Method F by using the compound represented by Formula (Za-6) in Production Method F in place of the compound represented by Formula (Zb-8). can be done.

式中、Ｒ１、Ｒ２、Ｙｃ、Ｒｙｃ、Ｒｙｇ、Ｒ６、Ｘ、およびＱは前記と同義である。[Manufacturing method S]

In the formula, R1, R2, Yc, Ryc, Ryg, R6, X and Q are as defined above.

In production method S, Ryg is a C1-C6 alkoxy group optionally substituted with a substituent C, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group optionally substituted with a substituent C, C2-C6 alkenyloxy group optionally substituted with substituent C, C2-C6 haloalkenyloxy group, C3-C6 alkynyloxy group optionally substituted with substituent C, C3-C6 halo an alkynyloxy group, a heteroaryl group optionally substituted with a substituent D, an aralkyloxy group optionally substituted with a substituent D, RaRbN- (wherein Ra and Rb are as defined above), Rc- L- (wherein Rc and L are as defined above), or represented by formula (Zb-11) which is Rx4Rx5C=NO- (wherein Rx4 and Rx5 are as defined above) It is a production method comprising reacting a compound represented by formula (Zb-8) with Ryg-Q in a solvent.

Preferred Ryc in the compound represented by formula (Zb-8) is a fluorine atom, a chlorine atom, or a bromine atom.

Ryg-Q used in this reaction is commercially available or can be produced by a known method. Preferred Q is a hydrogen atom or alkali metals such as sodium and potassium.

Carrying out Production Method S according to Production Method G by using the compound represented by Formula (Za-6) in Production Method G in place of the compound represented by Formula (Zb-8). can be done.

式中、Ｒ１、Ｒ２ａ、Ｒｙａ、Ｒ６、ＸおよびＹは前記と同義である。[Manufacturing method T]

In the formula, R1, R2a, Rya, R6, X and Y are as defined above.

Production method T is a method for synthesizing a compound represented by formula (Zb-13) having a hydroxyl group at R2a among the compounds represented by formula (1), and represented by formula (Zb-12) A production method comprising obtaining by reacting a compound and an acid in a solvent.

Acids used in this reaction include boron halides such as boron trichloride and boron tribromide.

Production method T can be carried out according to production method C by using the compound represented by formula (Za-3) in production method C in place of the compound represented by formula (Zb-12). can.

式中、Ｒ１、Ｒ２ａ、Ｒｙｂ、Ｒ６、Ｘ、ＹおよびＬｖは前記と同義である。[Manufacturing method U]

In the formula, R1, R2a, Ryb, R6, X, Y and Lv are as defined above.

In the production method U, among the compounds represented by formula (1), Ryb-O- may be optionally substituted with a substituent C, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a substituent C A C3-C8 cycloalkoxy group optionally substituted with a C2-C6 alkenyloxy group optionally substituted with a substituent C, a C2-C6 haloalkenyloxy group optionally substituted with a substituent C a C3-C6 alkynyloxy group, a C3-C6 haloalkynyloxy group, an aralkyloxy group optionally substituted with a substituent D, or Rx1C(=O)O-(Rx1 is as defined above .), wherein the compound represented by the formula (Zb-13) and Ryb-Lv are reacted in a solvent in the presence of a base. It is a manufacturing method including

Ryb-Lv used in this reaction can be obtained as a commercial product or produced by a known method.

Carrying out production method U according to production method D by using the compound represented by formula (Za-4) in production method D in place of the compound represented by formula (Zb-13) can be done.

式中、Ｒｙｄ－Ｂは有機ボロン酸類を表し、Ｒ１、Ｒ２ｃ、Ｒｙｃ、Ｒｙｄ、Ｒ６、Ｘ、およびＹは前記と同義である。[Manufacturing method V]

In the formula, Ryd-B represents an organic boronic acid, and R1, R2c, Ryc, Ryd, R6, X and Y are as defined above.

In production method V, among the compounds represented by formula (1), Ryd is a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group optionally substituted with a substituent C, a C3-C8 cycloalkyl group optionally substituted with a substituent C, a C2-C6 alkenyl group optionally substituted with a substituent C, a C2-C6 haloalkenyl group, an aryl group optionally substituted with a substituent D, or A method for synthesizing a compound represented by the formula (Zb-16), which is a heteroaryl group optionally substituted with a substituent D, comprising a compound represented by the formula (Zb-15) and a compound represented by Ryd-B It is a production method including obtaining by Suzuki-Miyaura coupling in which organic boronic acids are reacted.

Preferred Ryc in the compound represented by formula (Za-13) is a chlorine atom, a bromine atom, or an iodine atom.

Ryd-B used in this reaction represents an organic boronic acid such as an organic boronic acid or an organic boronic acid ester, and can be obtained as a commercial product or produced by a known method.

Production method V can be carried out according to production method E by using the compound represented by formula (Za-6) in production method E in place of the compound represented by formula (Zb-15). can.

式中、Ｒ１、Ｒ２ｃ、Ｒｙｃ、Ｒｙｅ、Ｒ６、ＸおよびＹは前記と同義である。[Manufacturing method W]

In the formula, R1, R2c, Ryc, Rye, R6, X and Y are as defined above.

In the production method W, among the compounds represented by the formula (1), Rye is a C2-C6 alkynyl group optionally substituted with a substituent C or a C2-C6 haloalkynyl group of the formula (Zb- 17) A method for synthesizing the compound represented by (Zb-15), wherein the compound represented by (Zb-15) and a terminal alkyne compound are reacted in the presence of transition metals and a base in a solvent to obtain by Sonogashira coupling. It is a manufacturing method including

In formula (Zb-15), Ryc is preferably a chlorine atom, a bromine atom, or an iodine atom.

The terminal alkyne compound used in this reaction can be obtained as a commercial product or produced by a known method. Trimethylsilylacetylene can also be used as the terminal alkyne compound. In this case, it is necessary to introduce a trimethylsilylethynyl group into the compound represented by the formula (Zb-15) and then desilylate it. For desilylation, see Journal of the American Chemical Society, Vol. 131, No. 2, pp. 634-643 (2009). and Journal of Organometallic Chemistry, Vol. 696, No. 25, pp. 4039-4045 (2011). It can be performed with reference to non-patent literature such as.

Production method W can be carried out according to production method F by using the compound represented by formula (Za-6) in production method F in place of the compound represented by formula (Zb-15). can.

式中、ＨａｌＲはハロゲン化剤を表し、Ｒ１、Ｒ２ｂ、Ｒｙｆ、Ｒ６、Ｘ、およびＹは前記と同義である。[Manufacturing method X]

In the formula, HalR represents a halogenating agent, and R1, R2b, Ryf, R6, X and Y are as defined above.

Production method X is a production method for obtaining a compound represented by formula (Zb-19), in which Ryf is a halogen atom, among the compounds represented by formula (1). A compound and a halogenating agent (HalR) are reacted in a solvent, or a compound represented by the formula (Zb-18) and a halogenating agent (HalR), and a radical initiator are reacted in a solvent It is a manufacturing method that also includes

Production method X can be carried out according to production method L by using the compound represented by formula (Za-16) in production method L in place of the compound represented by formula (Zb-18). can.

式中、ＨａｌＲはハロゲン化剤を表し、Ｒ１、Ｒ２、Ｒｙｆ、ＸおよびＹは前記と同義である。[Manufacturing method Y]

In the formula, HalR represents a halogenating agent, and R1, R2, Ryf, X and Y are as defined above.

Production method Y is a production method for obtaining a compound represented by formula (Zb-21), in which Ryf is a halogen atom, among the compounds represented by formula (1). It is a production method comprising reacting a compound to be obtained and a halogenating agent (HalR) in a solvent.

Halogenating agents used in this reaction include selectrofluor (N-fluoro-N'-triethylenediamine bis(tetrafluoroborate)), N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, 1 ,3-dichloro-5,5-dimethylhydantoin, 1,3-dibromo-5,5-dimethylhydantoin, 1,3-diiodo-5,5-dimethylhydantoin, bromine, iodine and the like.

The amount of the halogenating agent used in this reaction is not particularly limited as long as it is 1 equivalent or more relative to the compound represented by formula (Zb-20), as long as the target reaction proceeds. Preferably, it is 1 equivalent or more and 10 equivalents or less. However, the amount of the halogenating agent containing hydantoin is not particularly limited as long as it is 0.5 equivalents or more as long as the intended reaction proceeds, and is preferably 1 equivalent or more and 5 equivalents or less.

When the halogenating agent used in this reaction is an iodinating agent, an acid such as an inorganic acid such as hydrochloric acid or sulfuric acid, or an organic acid such as acetic acid, trifluoroacetic acid, methanesulfonic acid or trifluoromethanesulfonic acid may be added. can be done.

When the halogenating agent used in this reaction is an iodinating agent, the amount of the acid used is 0.01 equivalent or more with respect to the compound represented by the formula (Zb-20). Although it is not particularly limited as long as it proceeds, it is preferably 0.1 equivalent or more and 3 equivalent or less.

The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds. , diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, and other ether solvents; methanol, ethanol, isopropanol, and other alcohol solvents; benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, and other benzene solvents. , ethyl acetate, isopropyl acetate, ester solvents such as butyl acetate, nitrile solvents such as acetonitrile, N-methylpyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide and other amide solvents, 1,3- Urea-based solvents such as dimethyl-2-imidazolidinone, halogen-based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride can be used. These solvents can be used singly or as a mixture of two or more at any ratio.

The amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but usually 3 to 200 times the weight of the compound represented by the formula (Zb-20) It is below.

The temperature for carrying out this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 0° C. or higher and 150° C. or lower or the boiling point of the solvent or lower.

As a post-treatment of the reaction, a liquid separation operation can be performed by adding water or a suitable aqueous solution to the reaction mixture. When using an aqueous solution, acidic aqueous solution with hydrochloric acid, sulfuric acid, ammonium chloride, etc. dissolved, alkaline aqueous solution with potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc. dissolved, thiosulfuric acid An aqueous solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved, a saline solution, or the like can be arbitrarily used. During the liquid separation operation, if necessary, benzene solvents such as toluene, xylene, benzene, chlorobenzene, and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate, diethyl ether, diisopropyl ether, methyl- Ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane, which are incompatible with water. It is possible to add In addition, these solvents can be used alone, or two or more of them can be mixed at any ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield.

Moisture can be removed from the reaction mixture containing the compound represented by formula (Zb-21) obtained above with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.

From the reaction mixture containing the compound represented by formula (Zb-21) obtained above, the solvent can be distilled off under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (Zb-21) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. with an appropriate solvent. It may be appropriately set according to the desired purity.

式中、ＬａはＳを表し、ＬｂはＳＯまたはＳＯ_２を表し、Ｏｘ’は酸化剤を表す。[Manufacturing method Z]

_In the formula, La represents S, Lb represents SO or SO2, and Ox' represents an oxidizing agent.

Production method Z is represented by formula (Lb) wherein Lb contained in R3, R4, R5, R6, R7, substituent A and substituent C in the compound represented by formula ( ₁ ) is SO or SO2 wherein La contained in R3, R4, R5, R6, R7, substituent A and substituent C in the compound represented by formula (1) is S A production method comprising reacting a compound represented by with an oxidizing agent (Ox') in a solvent.

Examples of the oxidizing agent used in this reaction include aqueous hydrogen peroxide and peroxides such as meta-chloroperbenzoic acid. Transition metals such as sodium tungstate can also be added.

The amount of the oxidizing agent used in this reaction is usually 1.0 equivalent or more and 1.2 equivalent or less with respect to the compound represented by the _formula (La) when producing SO. When carrying out, it is usually 2 equivalents or more and 10 equivalents or less. Moreover, when adding transition metals, it is usually 0.001 equivalent or more and 1 equivalent or less.

The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds. Examples include benzene-based solvents, nitrile-based solvents such as acetonitrile, and halogen-based solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride. These solvents can be used singly or as a mixture of two or more at any ratio.

The amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times the weight of the compound represented by the formula (La). be.

The temperature for carrying out this reaction is not particularly limited as long as the desired reaction proceeds, but it is usually -10° C. or higher and 120° C. or lower or the boiling point of the solvent or lower.

As a post-treatment of the reaction, a liquid separation operation can be performed by adding water or a suitable aqueous solution to the reaction mixture. When using an aqueous solution, acidic aqueous solution with hydrochloric acid, sulfuric acid, ammonium chloride, etc. dissolved, alkaline aqueous solution with potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc. dissolved, thiosulfuric acid An aqueous solution in which a sulfur-containing salt such as sodium or sodium sulfite is dissolved, a saline solution, or the like can be arbitrarily used. During the liquid separation operation, if necessary, benzene solvents such as toluene, xylene, benzene, chlorobenzene, and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate, diethyl ether, diisopropyl ether, methyl- Ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane, which are incompatible with water. It is possible to add In addition, these solvents can be used alone, or two or more of them can be mixed at any ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield.

The reaction mixture containing the compound represented by formula (Lb) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.

The solvent can be distilled off from the reaction mixture containing the compound represented by formula (Lb) obtained above under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (Lb) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, or the like with an appropriate solvent. It may be appropriately set according to the desired purity.

Next, a method for synthesizing the compound represented by formula (2) described in Production Method A will be described.

式中、Ｒ２、Ｒ７、ＸおよびＹは、前記と同義である。[Manufacturing method AA]

In the formula, R2, R7, X and Y are as defined above.

Production method AA is a method for producing a production intermediate represented by formula (2), wherein the compound represented by formula (4) and the compound represented by formula (5) are mixed in a solvent or without a solvent. It is a manufacturing method including reacting.

The compound represented by Formula (4) used in this reaction can be synthesized according to Reference Examples. Also, Green Chemistry, Vol. 41, pp. 580-585; The Journal of Organic Chemistry, Vol. 65, No. 20, pp. 6458-6461 (2000); Synthesis can also be performed by referring to ORGANIC LETTERS, Vol. 9, No. 4, pp. 667-669 (2007).

The compound represented by formula (5) used in this reaction can be obtained as a commercial product or produced by a known method.

The amount of the compound represented by formula (5) used in this reaction is particularly limited as long as it is 1 equivalent or more relative to the compound represented by formula (4), as long as the desired reaction proceeds. but preferably 1 equivalent or more and 10 equivalents or less.

Solvents used in this reaction include ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran and dioxane; benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene; ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate; nitrile solvents such as acetonitrile; amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide and N,N-dimethylacetamide; 1,3-dimethyl -Urea solvents such as 2-imidazolidinone; halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride; sulfur solvents such as dimethylsulfoxide and sulfolane; ketone solvents such as acetone, methyl ethyl ketone and methyl isobutyl ketone; and compounds represented by formula (5). A compound represented by formula (5) can be used as a solvent. These solvents can be used singly or as a mixture of two or more at any ratio.

The amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times the weight of the compound represented by the formula (4). be.

The temperature for carrying out this reaction is not particularly limited as long as the desired reaction proceeds, but it is usually -50° C. or higher and 150° C. or lower or the boiling point of the solvent or lower.

As a post-treatment of the reaction, a liquid separation operation can be performed by adding water or a suitable aqueous solution to the reaction mixture. When an aqueous solution is used, an acidic aqueous solution with hydrochloric acid, sulfuric acid, etc. dissolved therein, an alkaline aqueous solution with potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc. dissolved therein, or salt water, etc. is optional. can be used for During the liquid separation operation, if necessary, benzene solvents such as toluene, xylene, benzene, chlorobenzene, and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate, diethyl ether, diisopropyl ether, methyl- Ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane, which are incompatible with water. It is possible to add In addition, these solvents can be used alone, or two or more of them can be mixed at any ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield.

The reaction mixture containing the compound represented by formula (2) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.

From the reaction mixture containing the compound represented by formula (2) obtained above, the solvent can be distilled off under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (2) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, or the like with an appropriate solvent. It may be appropriately set according to the desired purity.

Next, a method for synthesizing the compound represented by formula (Zb-1) described in Production Method M will be described.

式中、Ｒ２、Ｒ６、ＸおよびＹは、前記と同義である。[Manufacturing method AB]

In the formula, R2, R6, X and Y are as defined above.

Production method AB is a method for producing a production intermediate represented by formula (Zb-1), wherein the compound represented by formula (6) and the compound represented by formula (7) are reacted under acidic conditions or with a base. It is a production method including reacting in a solvent under toxic conditions.

The compound represented by Formula (6) used in this reaction can be synthesized according to Reference Examples. Alternatively, it can be synthesized by referring to Tetrahedron, 2012, Vol. 68, pp. 9598-9605.

The compound represented by formula (7) used in this reaction can be obtained as a commercial product or produced by a known method.

The amount of the compound represented by formula (7) used in this reaction is particularly limited as long as it is 1 equivalent or more relative to the compound represented by formula (6), as long as the desired reaction proceeds. but preferably 1 equivalent or more and 10 equivalents or less.

First, the reaction under acidic conditions will be described.

Acids used in this reaction include inorganic acids such as hydrochloric acid, hydrobromic acid and phosphoric acid, and organic acids such as acetic acid, methanesulfonic acid, p-toluenesulfonic acid and trifluoroacetic acid. There are no particular limitations as long as the intended reaction proceeds.

The amount of acid used in this reaction may be a catalytic amount, and is not particularly limited as long as the intended reaction proceeds, but preferably 0.00 to the compound represented by formula (6). 01 equivalents or more. Liquid acids can also be used as solvents.

The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds. Ether solvents such as butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane, alcohol solvents such as methanol, ethanol, and isopropanol, benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene, ethyl acetate, isopropyl acetate, and acetic acid. ester solvents such as butyl, nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, 1,3-dimethyl-2-imidazolidinone, etc. and halogen-based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride. These solvents can be used singly or as a mixture of two or more at any ratio.

The amount of the solvent used in this reaction is not particularly limited as long as the intended reaction proceeds, but is usually 3 to 200 times the weight of the compound represented by the formula (6). be.

The temperature for carrying out this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 0° C. or higher and 180° C. or lower or the boiling point of the solvent or lower.

Next, the reaction under basic conditions will be described.

The base used in this reaction is exemplified by inorganic bases such as lithium hydroxide, sodium hydroxide and potassium hydroxide, but is not particularly limited as long as the desired reaction proceeds.

The base used in this reaction is not particularly limited as long as it is 1 equivalent or more relative to the compound represented by formula (6), as long as the target reaction proceeds, but preferably 1 equivalent or more. 30 equivalents or less.

The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds. alcohol solvents such as methanol, ethanol, and isopropanol; benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene; ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate; nitriles such as acetonitrile. amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide and N,N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, dichloromethane, dichloroethane, chloroform, Examples thereof include halogen-based solvents such as carbon tetrachloride. These solvents can be used singly or as a mixture of two or more at any ratio.

The amount of the solvent used in this reaction is not particularly limited as long as the intended reaction proceeds, but is usually 3 to 200 times the weight of the compound represented by the formula (6). be.

The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but it is usually from -20°C to 180°C or below the boiling point of the solvent.

Post-treatment of the reaction can be carried out by a common method for the reaction under acidic conditions and the reaction under basic conditions. A liquid separation operation can be performed by adding water or a suitable aqueous solution to the reaction mixture. When an aqueous solution is used, an acidic aqueous solution with hydrochloric acid, sulfuric acid, etc. dissolved therein, an alkaline aqueous solution with potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc. dissolved therein, saline solution, etc. is optional. can be used for During the liquid separation operation, if necessary, benzene solvents such as toluene, xylene, benzene, chlorobenzene, and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate, diethyl ether, diisopropyl ether, methyl- Ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane, which are incompatible with water. It is possible to add In addition, these solvents can be used alone, or two or more of them can be mixed at any ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield.

The reaction mixture containing the compound represented by formula (Zb-1) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.

From the reaction mixture containing the compound represented by formula (Zb-1) obtained above, the solvent can be distilled off under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (Zb-1) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. with an appropriate solvent. It may be appropriately set according to the desired purity.

（式中、Ｒ２、Ｒ６、ＸおよびＹは前記と同義である。）
で表される異性体も含む。The compound represented by the formula (Zb-1) has the formula (Zb-1′)

(Wherein, R2, R6, X and Y are as defined above.)
Also includes isomers represented by

The compound represented by formula (Zb-1') can be handled in the same manner as the compound represented by formula (Zb-1), and production method M can be applied. Also, a mixture of the compound represented by the formula (Zb-1) and the compound represented by the formula (Zb-1') may be used, and the isomer mixture ratio may be either singly or as a mixture at any ratio.

The compound represented by formula (1) or a salt thereof can be produced by arbitrarily combining the production methods A to AB shown above. Alternatively, the compound represented by formula (1) or a salt thereof can be produced by any combination of known methods and production methods A to AB.

The compound of the present invention can be used as an agricultural chemical because it can control organisms that are harmful to plants. Specific examples include fungicides, insecticides, herbicides, plant growth regulators and the like. Preferably, it is a disinfectant.

The compound of the present invention can be used as an agricultural and horticultural fungicide in upland fields, paddy fields, tea gardens, orchards, pastures, lawns, forests, gardens, roadside trees, etc. for controlling plant diseases.

The term "plant disease" as used in the present invention refers to systemic abnormal pathological symptoms such as wilting, damping, yellowing, atrophy, and elongation in plants such as crops, flowers, flowering trees, and trees, or spots, leaf blight, and mosaic disease. , cigars, withered branches, root rot, root knots, galls, and other partial pathological symptoms are induced. That is, plants become sick. Pathogens that cause plant diseases mainly include fungi, bacteria, spiroplasma, phytoplasma, viruses, viroids, parasitic higher plants, and nematodes. Although the compounds of the present invention are effective against fungi, they are not so limited.

Diseases caused by fungi are primarily fungal diseases. Fungi (pathogens) that cause fungal diseases include Necromycota, Oomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycota, and the like. For example, clubroot fungi include clubroot fungi, potato powdery scab fungi, sugar beet root fungi, oomycetes such as phytophthora, downy mildew, Pythium spp. and Aphanomyces spp. Peach leaf curl fungus, corn sesame leaf blight, rice blast fungus, powdery mildew, anthracnose, Fusarium head blight, bakanae fungus, sclerotinia, basidiomycete rust fungi, smut fungi, and purpura Examples of feather fungi, blast fungi, sheath blight fungi, and imperfect fungi include botrytis, Alternaria, Fusarium, Penicillium, Rhizoctonia, and white silkworms.

The compounds of the present invention are effective against various plant diseases. Specific examples of disease names and pathogen names are shown below.

Rice blast (Magnaporthe grisea), sheath blight (Thanatephorus cucumeris), brown sclerotia (Ceratobasidium setariae), brown sclerotia (Waitea circinata), brown wilt (Thanatephorus cucumeris), sclerotidosis ( Sclerotium hydrophilum, Wairea circinata, Entyloma dactylidis, Magnaporthe salvinii, Ceratobasidium cornigerum, Cochiliobolus leaf blight Sphaerulina oryzina, Gibberella fujikuroi, Pythium spp., Fusarium spp., Trichoderma spp., Rhizopus spp., Rhizoctonia solani, Mucorsph. disease (Pythium spp., Achlya spp., Dictyuchus spp.), rice malt (Claviceps virens), ink smut (Tilletia barclayana), brown rice (Curvularia spp., Alternaria spp.), yellow dwarf disease (Sclerophthorap) ), bacterial blight (Xanthomonas oryzae pv. oryzae), brown streak (Acidovorax avenae subsp. ), Pseudomonas fuscovaginae, Pseudomonas syringae pv.oryzae, Erwinia chrysanthemi, Phytoplasma oryzae, Rice stripe tenuivirus Rice dwarf reovirus);
Wheat powdery mildew (Blumeria graminis f.sp.hordei; f.sp.tritici), rust (Puccinia striiformis, Puccinia graminis, Puccinia recondita, Puccinia hordei), leaf spot (Pyrenophora gramine), leaf spot (Pyrenophora gramine) Ｐｙｒｅｎｏｐｈｏｒａ ｔｅｒｅｓ）、赤かび病（Ｇｉｂｂｅｒｅｌｌａ ｚｅａｅ、Ｆｕｓａｒｉｕｍ ｃｕｌｍｏｒｕｍ、Ｆｕｓａｒｉｕｍ ａｖｅｎａｃｅｕｍ、Ｍｏｎｏｇｒａｐｈｅｌｌａ ｎｉｖａｌｉｓ）、雪腐病（Ｔｙｐｈｕｌａ ｉｎｃａｒｎａｔａ、Ｔｙｐｈｕｌａ ｉｓｈｉｋａｒｉｅｎｓｉｓ、Ｍｏｎｏｇｒａｐｈｅｌｌａ ｎｉｖａｌｉｓ）、裸黒穂病（Ｕｓｔｉｌａｇｏ ｎｕｄａ）、なまぐさ黒穂病（Ｔｉｌｌｅｔｉａ ｃａｒｉｅｓ、 Ｔｉｌｌｅｔｉａ ｃｏｎｔｒｏｖｅｒｓａ）、眼紋病（Ｐｓｅｕｄｏｃｅｒｃｏｓｐｏｒｅｌｌａ ｈｅｒｐｏｔｒｉｃｈｏｉｄｅｓ）、株腐病（Ｃｅｒａｔｏｂａｓｉｄｉｕｍ ｇｒａｍｉｎｅｕｍ）、雲形病（Ｒｈｙｎｃｈｏｓｐｏｒｉｕｍ ｓｅｃａｌｉｓ）、葉枯病（Ｓｅｐｔｏｒｉａ ｔｒｉｔｉｃｉ）、ふ枯病（Ｐｈａｅｏｓｐｈａｅｒｉａ ｎｏｄｏｒｕｍ）、苗立枯病（Ｆｕｓａｒｉｕｍ ｓｐｐ ．、Ｐｙｔｈｉｕｍ ｓｐｐ．、Ｒｈｉｚｏｃｔｏｎｉａ ｓｐｐ．、Ｓｅｐｔｏｒｉａ ｓｐｐ．、Ｐｙｒｅｎｏｐｈｏｒａ ｓｐｐ．）、立枯病（Ｇａｅｕｍａｎｎｏｍｙｃｅｓ ｇｒａｍｉｎｉｓ）、炭疽病（Ｃｏｌｌｅｔｏｔｒｉｃｈｕｍ ｇｒａｍｉｎｉｃｏｌａ）、麦角病（Ｃｌａｖｉｃｅｐｓ ｐｕｒｐｕｒｅａ）、斑点病（Ｃｏｃｈｌｉｏｂｏｌｕｓ ｓａｔｉｖｕｓ）、黒節diseases (Pseudomonas syringae pv. syringae);
Fusarium head blight of corn (Gibberella zeae, etc.), seedling blight (Fusarium avenaceum, Penicillium spp, Pythium spp., Rhizoctonia spp.), rust (Puccinia sorghi), leaf blight (Cochliobolus heterostrophus), smut (cochliobolus heterostrophus) Ｕｓｔｉｌａｇｏ ｍａｙｄｉｓ）、炭疽病（Ｃｏｌｌｅｔｏｔｒｉｃｈｕｍ ｇｒａｍｉｎｉｃｏｌａ）、北方斑点病（Ｃｏｃｈｌｉｏｂｏｌｕｓ ｃａｒｂｏｎｕｍ）、褐条病（Ａｃｉｄｏｖｏｒａｘ ａｖｅｎａｅ ｓｕｂｓｐ． ａｖｅｎａｅ）、条斑細菌病（Ｂｕｒｋｈｏｌｄｅｒｉａ ａｎｄｒｏｐｏｇｏｎｉｓ）、倒伏細菌病（Ｅｒｗｉｎｉａ ｃｈｒｙｓａｎｔｈｅｍｉ ｐｖ． ｚｅａｅ）、 Bacterial wilt disease (Erwinia stewartii); Grape downy mildew (Plasmopara viticola), Rust (Physopella ampelopsidis), Powdery mildew (Uncinula necator), Black rot (Elsinoe ampelina), Late rot (Glomerella cingulata, Glomerella cingulata, acutatum), Guignardia bidwellii, Phomopsis viticola, Zygophiala jamaicensis, Botrytis cinerea, Diaporthememia medusaea, Heliupicobasae ), Rosellinia necatrix, Agrobacterium vitis; Podosphaera leucotricha of apples, Venturia inaequalis, Alternaria mali, Red star ( Gymnosporangium yamadae), Monilinia mali, rot (Valsa ceratosperma), ring blight (Botryosphaeria berengeriana), anthracnose (Colletotrichum acutatum, Glomerella cingulata) amaicensis), soot spot (Gloeodes pomigena), black spot (Mycosphaerella pomi), purple spot (Helicobasidium moma), white spot (Rosellinia necatrix), body blight (Phomopsis mali, Diaporthe tanak) (Diplocarpon mali), apple burn (Erwinia amylovora), root canker (Agrobacterium tumefaciens), hairy root disease (Agrobacterium rhizogenes);
Alternaria kikuchiana, Venturia nashicola, Gymnosporangium asiaticum, Botryosphaeria bengeriana f.sp. Ｅｒｗｉｎｉａ ｓｐ．）、根頭がんしゅ病（Ａｇｒｏｂａｃｔｅｒｉｕｍ ｔｕｍｅｆａｃｉｅｎｓ）、さび色胴枯病（Ｅｒｗｉｎｉａ ｃｈｒｙｓａｎｔｈｅｍｉ ｐｖ． ｃｈｒｙｓａｎｔｈｅｍｉ）、花腐細菌病（Ｐｓｅｕｄｏｍｏｎａｓ ｓｙｒｉｎｇａｅ ｐｖ． ｓｙｒｉｎｇａｅ）；セイヨウナシの疫病（Ｐｈｙｔｏｐｈｔｈｏｒａ ｃａｃｔｏｒｕｍ、 Ｐｈｙｔｏｐｈｔｈｏｒａ syringae, bacterial shoot blight (Erwinia sp.); peach scab (Cladosporium carpophilum), Phomopsis sp., phytophthora sp. deformans), perforating bacterial disease (Xhanthomonas campestris pv. pruni), root canker disease (Agrobacterium tumefaciens); ）、根頭がんしゅ病（Ａｇｒｏｂａｃｔｅｒｉｕｍ ｔｕｍｅｆａｃｉｅｎｓ）、樹脂細菌病（Ｐｓｅｕｄｏｍｏｎａｓ ｓｙｒｉｎｇａｅ ｐｖ． ｓｙｒｉｎｇａｅ）；カキの炭疽病（Ｇｌｏｍｅｒｅｌｌａ ｃｉｎｇｕｌａｔａ）、落葉病（Ｃｅｒｃｏｓｐｏｒａ ｋａｋｉ； Ｍｙｃｏｓｐｈａｅｒｅｌｌａ ｎａｗａｅ）、うどんこ病（Ｐｈｙｌｌａｃｔｉｎｉａ ｋａｋｉｋｏｒａ） , Agrobacterium tumefaciens; Diaporthe citri, Penicillium digitatum, Penicillium italicum, Elsinoe fawcettii, Phytoph hora citrophthora), canker (Xhanthomonas campestris pv. citri), Pseudomonas syringae pv. syringae, Liberibacter asiaticus, Agrobacterium tumefaciens;
Botrytis cinerea of tomatoes, cucumbers, beans, strawberries, potatoes, cabbage, eggplants, lettuce, etc.; ); Seedling blight of various vegetables such as tomato, cucumber, beans, radish, watermelon, eggplant, rapeseed, green pepper, spinach, sugar beet (Rhizoctonia spp., Pythium spp., Fusarium spp., Phythophthora spp., Sclerotinia sclerotiorum, etc.) Solanaceous plant wilt (Ralstonia solanacearum); downy mildew of cucurbits (Pseudoperonospora cubensis), powdery mildew (Sphaerotheca fuliginea), anthracnose (Colletotrichum orbiculare), vine wilt (Didymella bryoni) （Ｆｕｓａｒｉｕｍ ｏｘｙｓｐｏｒｕｍ）、疫病（Ｐｈｙｔｏｐｈｔｈｏｒａ ｐａｒａｓｉｔｉｃａ、Ｐｈｙｔｏｐｈｔｈｏｒａ ｍｅｌｏｎｉｓ、Ｐｈｙｔｏｐｈｔｈｏｒａ ｎｉｃｏｔｉａｎａｅ、Ｐｈｙｔｏｐｈｔｈｏｒａ ｄｒｅｃｈｓｌｅｒｉ、Ｐｈｙｔｏｐｈｔｈｏｒａ ｃａｐｓｉｃｉ等）、褐斑細菌病（Ｘｈａｎｔｈｏｍｏｎａｓ ｃａｍｐｅｓｔｒｉｓ ｐｖ．ｃｕｃｕｒｂｉｔａｅ）、軟腐病（Ｅｒｗｉｎｉａ ｃａｒｏｔｏｖｏｒａ ｓｕｂｓｐ． ｃａｒｏｔｏｖｏｒａ）、斑点細菌病（ Pseudomonas syringae pv. lachrymans, Pseudomonas marginalis pv. marginalis, Streptomyces sp., Agrobacterium rhizogenes, Cucumber mosaic virus;
トマトの輪紋病（Ａｌｔｅｒｎａｒｉａ ｓｏｌａｎｉ）、葉かび病（Ｆｕｌｖｉａ ｆｕｌｖａ）、疫病（Ｐｈｙｔｏｐｈｔｈｏｒａ ｉｎｆｅｓｔａｎｓ）、萎凋病（Ｆｕｓａｒｉｕｍ ｏｘｙｓｐｏｒｕｍ）、根腐病（Ｐｙｔｈｉｕｍ ｍｙｒｉｏｔｙｌｕｍ、Ｐｙｔｈｉｕｍ ｄｉｓｓｏｔｏｃｕｍ）、炭疽病（Ｃｏｌｌｅｔｏｔｒｉｃｈｕｍ ｇｌｏｅｏｓｐｏｒｉｏｉｄｅｓ）、かいよう病（Ｃｌａｖｉｂａｃｔｅｒ ｍｉｃｈｉｇａｎｅｎｓｉｓ）、茎えそ細菌病（Ｐｓｅｕｄｏｍｏｎａｓ ｃｏｒｒｕｇａｔａ）、黒斑細菌病（Ｐｓｅｕｄｏｍｏｎａｓ ｖｉｒｉｄｉｆｌａｖａ）、軟腐病（Ｅｒｗｉｎｉａ ｃａｒｏｔｏｖｏｒａ ｓｕｂｓｐ． ｃａｒｏｔｏｖｏｒａ）、葉こぶ病（Ｃｒｙｎｅｂａｃｔｅｒｉｕｍ ｓｐ．）、萎黄病（Ｐｈｙｔｏｐｌａｓｍａ ａｓｔｅｒｉｓ） , yellow dwarf disease (Tobacco leaf curl subgroup III geminivirus); eggplant powdery mildew (Sphaerotheca fuliginea, etc.), soot blight (Mycovellosiella nattrassii), late blight (Phytophthora infestans), brown rot (Phytophthora infestans), brown rot (Phytophthora infestans) Pseudomonas cichorii, Pseudomonas corrugata, Erwinia chrysanthemi, Erwinia carotovora subsp. carotovora, Pseudomonas sp. Alternaria brassicae), Black rot (Xhanthomonas campestris pv. campestris), Pseudomonas syringae pv. maculicola, Soft rot (Erwinia carotovora); Cruciferous vegetable black spot (Alternaria brasica, etc.) Cercosporella brassicae), root rot (Phoma lingam), clubroot (Plasmodiophora brassicae), downy mildew (Peronospora parasitica), black rot (Xhanthomonas campestris pv. campestris), Pseudomonas syringae pv. maculicola), soft rot (Erwinia carotovora subsp. carotovora);
Cabbage stock rot (Thanatephorus cucumeris), chlorosis (Fusarium oxysporum), black soot (Alternaria brassicola); Chinese cabbage bottom rot (Rhizoctonia solani), yellow spot (Verticillium dahliae); ), Alternaria porri, Sclerotium rolfsii, Phytophthora porri, Sclerotium cepivorum; ． ｃａｒｏｔｏｖｏｒａ）、斑点細菌病（Ｐｓｅｕｄｏｍｏｎａｓ ｓｙｒｉｎｇａｅ ｐｖ． ｓｙｒｉｎｇａｅ）、腐敗病（Ｅｒｗｉｎｉａ ｒｈａｐｏｎｔｉｃｉ）、鱗片腐敗病（Ｂｕｒｋｈｏｌｄｅｒｉａ ｇｌａｄｉｏｌｉ）、萎黄病（Ｐｈｙｔｏｐｌａｓｍａ ａｓｔｅｒｉｓ）；ニンニクの軟腐病（Ｅｒｗｉｎｉａ ｃａｒｏｔｏｖｏｒａ ｓｕｂｓｐ． ｃａｒｏｔｏｖｏｒａ）、春Pseudomonas marginalis pv. marginalis; soybean purpura (Cercospora kikuchii), Elsinoe glycines, Diaporthe phaselorum, Rhizoctonia solani, Stem rot (Ph.べと病（Ｐｅｒｏｎｏｓｐｏｒａ ｍａｎｓｈｕｒｉｃａ）、さび病（Ｐｈａｋｏｐｓｏｒａ ｐａｃｈｙｒｈｉｚｉ）、炭疽病（Ｃｏｌｌｅｔｏｔｒｉｃｈｕｍ ｔｒｕｎｃａｔｕｍ等）、葉焼病（Ｘｈａｎｔｈｏｍｏｎａｓ ｃａｍｐｅｓｔｒｉｓ ｐｖ． ｇｌｙｃｉｎｅｓ）、斑点細菌病（Ｐｓｅｕｄｏｍｏｎａｓ ｓｙｒｉｎｇａｅ ｐｖ． ｇｌｙｃｉｎｅａ）；インゲンの炭疽病（ Colletotrichum lindemuthianum), bacterial wilt (Ralstonia solanacearum), lint wilt (Pseudomonas syringae pv. phaseolicola), brown spot bacterial disease (Pseudomonas viridiflava) ), leaf scorch (Xhanthomonas campestris pv. phaseoli);
Peanut black stain (Mycosphaerella berkeleyi), brown spot (Mycosphaerella arachidis), bacterial wilt (Ralstonia solanacearum); syringae pv. pisi), vine rot (Xhanthomonas campestris pv. pisi); broad bean downy mildew (Peronospora viciae), late blight (Phytophthora nicotianae);疫病（Ｐｈｙｔｏｐｈｔｈｏｒａ ｉｎｆｅｓｔａｎｓ）、銀か病（Ｈｅｌｍｉｎｔｈｏｓｐｏｒｉｕｍ ｓｏｌａｎｉ）、乾腐病（Ｆｕｓａｒｉｕｍ ｏｘｙｓｐｏｒｕｍ、Ｆｕｓａｒｉｕｍ ｓｏｌａｎｉ）、粉状そうか病（Ｓｐｏｎｇｏｓｐｏｒａ ｓｕｂｔｅｒｒａｎｅａ）、青枯病（Ｒａｌｓｔｏｎｉａ ｓｏｌａｎａｃｅａｒｕｍ）、黒あし病（Ｅｒｗｉｎｉａ ｃａｒｏｔｏｖｏｒａ ｓｕｂｓｐ ． ａｔｒｏｓｅｐｔｉｃａ）、そうか病（Ｓｔｒｅｐｔｏｍｙｃｅｓ ｓｃａｂｉｅｓ、Ｓｔｒｅｐｔｏｍｙｃｅｓ ａｃｉｄｉｓｃａｂｉｅｓ）、軟腐病（Ｅｒｗｉｎｉａ ｃａｒｏｔｏｖｏｒａ ｓｕｂｓｐ． ｃａｒｏｔｏｖｏｒａ）、粘性腐敗病（Ｃｒｏｓｔｒｉｄｉｕｍ ｓｐｐ．）、輪腐病（Ｃｌａｖｉｂａｃｔｅｒ ｍｉｃｈｉｇａｎｅｎｓｉｓ ｓｕｂｓｐ．ｓｅｐｅｄｏｎｉｃｕｓ）；サツマイモの立枯病Cercospora beticola, Peronospora schachtii, Aphanomyces cochioides, Phoma betae, Agrobacterium tumefaciens, disease (Streptomyces scabies), bacterial spot (Pseudomonas syringae pv. aptata);
Alternaria dauci of carrots, Rhizobacter dauci, Agrobacterium tumefaciens, Streptomyces spp., Erwinia carotovora subsp. Strawberry powdery mildew (Sphaerotheca aphanis var. aphanis), late blight (Phytophthora nicotianae, etc.), anthracnose (Glomerella cingulata, etc.), fruit rot (Pythium ultimum), bacterial wilt (Ralstonia solanacearum), horn spot bacteria campestris, Pseudomonas marginalis pv. marginalis; Exobasidium reticulatum, Elsinoe leucospira, Colletotrichum theae-sinensis, Pesistalo Pseudomonas syringae pv. theae, Xhanthomonas campestris pv. theicola, Pseudomonas sp.; ｇｌｏｅｏｓｐｏｒｉｏｉｄｅｓ）、疫病（Ｐｈｙｔｏｐｈｔｈｏｒａ ｎｉｃｏｔｉａｎａｅ）、野火病（Ｐｓｅｕｄｏｍｏｎａｓ ｓｙｒｉｎｇａｅ ｐｖ．ｔａｂａｃｉ）、黄がさ細菌病（Ｐｓｅｕｄｏｍｏｎａｓ ｓｙｒｉｎｇａｅ ｐｖ．ｍｅｌｌｅａ）、空洞病（Ｅｒｗｉｎｉａ ｃａｒｏｔｏｖｏｒａ ｓｕｂｓｐ． ｃａｒｏｔｏｖｏｒａ）、立枯病（Ｒａｌｓｔｏｎｉａ ｓｏｌａｎａｃｅａｒｕｍ）、 Tobacco mosaic virus;
coffee rust (Hemileia vastatrix); banana black sigatoga (Mycosphaerella fijiensis), Panama disease (Fusarium oxysporum f.sp cubense); cotton wilt (Fusarium oxysporum), white mold (Ramularia; sunflower)菌核病（Ｓｃｌｅｒｏｔｉｎｉａ ｓｃｌｅｒｏｔｉｏｒｕｍ）、角点病（Ｘｈａｎｔｈｏｍｏｎａｓ ｃａｍｐｅｓｔｒｉｓ ｐｖ．ｍａｌｖａｃｅａｒｕｍ）、空洞病（Ｅｒｗｉｎｉａ ｃａｒｏｔｏｖｏｒａ ｓｕｂｓｐ． ｃａｒｏｔｏｖｏｒａ）、斑点細菌病（Ｐｓｅｕｄｏｍｏｎａｓ ｓｙｒｉｎｇａｅ ｐｖ．ｈｅｌｉａｎｔｈｉ）；バラの黒星病（Ｄｉｐｌｏｃａｒｐｏｎ ｒｏｓａｅ）、うどんThis disease (Sphaerotheca pannosa, etc.), Late blight (Phytophthora megasperma), Downy mildew (Peronospora sparsa), Agrobacterium tumefaciens; 、疫病（Ｐｈｙｔｏｐｈｔｈｏｒａ ｃａｃｔｏｒｕｍ）、斑点細菌病（Ｐｓｅｕｄｏｍｏｎａｓ ｃｉｃｈｏｒｉｉ）、軟腐病（Ｅｒｗｉｎｉａ ｃａｒｏｔｏｖｏｒａ ｓｕｂｓｐ． ｃａｒｏｔｏｖｏｒａ）、根頭がんしゅ病（Ａｇｒｏｂａｃｔｅｒｉｕｍ ｔｕｍｅｆａｃｉｅｎｓ）、毛根病（Ａｇｒｏｂａｃｔｅｒｉｕｍ ｒｈｉｚｏｇｅｎｅｓ）、緑化病（Ｐｈｙｔｏｐｌａｓｍａ ａｕｒａｎｔｉｆｏｌｉａ）； Lawn brown patch (Rhizoctonia solani), Dollar spot (Sclerotinia homoeocarpa), Curvularia sp., Rust (Puccinia zoysiae), Helmintosporium leaf blight (Cochliobolus sp.), cloud form (Rhynchosporium secalis), wilt disease (Gaeumannomyces graminis), anthracnose (Colletotrichum sp.), snow rot brown small sclerotinia (Typula incarnata), snow rot black small sclerotinia (Typhula ishikariensis), snow rot large sclerotinia disease (Myrioscl erotinia borealis), fairy ring disease (Marasmius oreades etc.), pythium disease (Pythium aphanidermatum etc.), blast disease (Pyricularia grisea) and the like.

The compound of the present invention may be used alone, but is preferably mixed with a solid carrier, liquid carrier, gaseous carrier, surfactant, sticking agent, dispersant, stabilizer, etc., and used as a powder or wettable powder. , wettable powders, aqueous solutions, aqueous granules, granules, emulsions, liquids, microemulsions, aqueous suspensions, aqueous emulsions, suspoemulsions and the like. As long as the effect is exhibited, it is not limited to those compositions.

Specific formulation examples are shown below, but are not limited to these.

[Formulation Example 1 Flowable agent]
Compound of the present invention (10 parts by mass), formaldehyde condensate sodium salt of naphthalenesulfonic acid (5 parts by mass), polyoxyethylene arylphenyl ether (1 part by mass), propylene glycol (5 parts by mass), silicone antifoaming agent ( 0.1 parts by mass), xanthan gum (0.2 parts by mass), and ion-exchanged water (78.7 parts by mass) were mixed to form a slurry, which was further wet-ground using glass beads with a diameter of 1.0 mm in a Dynomill KDL. and obtain a flowable agent.

[Formulation Example 2 Emulsion]
The compound of the present invention (5 parts by mass) is dissolved in a mixed solution of xylene (40 parts by mass) and cyclohexane (35 parts by mass), and Tween 20 (20 parts by mass) is added and mixed to obtain an emulsion.

[Formulation Example 3 wettable powder]
Compound of the present invention (10 parts by mass), white carbon (10 parts by mass), polyvinyl alcohol (2 parts by mass), sodium dioctylsulfosuccinate (0.5 parts by mass), sodium alkylbenzenesulfonate (5 parts by mass), baking Diatomaceous earth (10 parts by mass) and kaolinite clay (62.5 parts by mass) are thoroughly mixed and pulverized with an air mill to obtain a wettable powder.

Examples of the method of applying the compound of the present invention or a composition containing it include a method of contacting with plants or seeds, or a method of including in cultivation soil and contacting roots or rhizomes of plants. Specific examples include foliage spray treatment, injection treatment, seedling box treatment, cell tray treatment, spray treatment on plant seeds, smear treatment on plant seeds, and plant seeds of the compound of the present invention or a composition containing it. immersion treatment, dressing treatment for plant seeds, spraying treatment on the soil surface, soil mixing after spraying treatment on the soil surface, injection treatment into soil, soil mixing after injection treatment in soil, soil Examples include irrigation treatment, soil mixing after soil irrigation treatment, and the like. Generally, any method of application as utilized by those skilled in the art will suffice.

The term "plant" as used in the present invention refers to a plant that performs photosynthesis and lives without movement. Specific examples include rice, wheat, barley, corn, coffee, bananas, grapes, apples, pears, peaches, cherry, oysters, citrus, soybeans, green beans, cotton, strawberries, potatoes, cabbage, lettuce, tomatoes, cucumbers, eggplants, Watermelons, sugar beets, spinach, snow peas, pumpkins, sugarcane, tobacco, green peppers, sweet potatoes, taro, konnyaku, cotton, sunflowers, roses, tulips, chrysanthemums, grass, etc. and their F1 varieties. It also includes genetically modified crops that are produced by artificially manipulating genes, etc. and do not originally exist in nature. , tobacco, etc., corn imparted with insecticidal substance-producing ability, and agricultural and horticultural crops such as cotton. Furthermore, trees such as pine, ash, ginkgo, maple, oak, poplar, and zelkova are included. In addition, the term "plant body" as used in the present invention is a general term for all parts constituting the above-described individual plant, and examples thereof include stems, leaves, roots, seeds, flowers, fruits, and the like.

The term "seed" as used in the present invention refers to a material that stores nutrients for seedling germination and is used for agricultural propagation. Specific examples include seeds such as corn, soybeans, cotton, rice, sugar beets, wheat, barley, sunflowers, tomatoes, cucumbers, eggplants, spinach, snow peas, pumpkins, sugarcane, tobacco, green peppers, and rapeseed, and their F1 varieties. Examples include seeds, seed potatoes such as taro, potato, sweet potato, and konnyaku, bulbs such as edible lilies and tulips, seed bulbs such as scallions, and seeds and tubers of genetically modified crops.

The application amount and application concentration of the compound of the present invention or a composition containing it vary depending on the target crop, target disease, degree of disease occurrence, formulation of the compound, application method, various environmental conditions, etc., but spraying or irrigation In some cases, the amount of active ingredient is suitably 0.1 to 10,000 g per hectare, preferably 10 to 1,000 g per hectare. The amount of the active ingredient used for seed treatment is 0.0001 to 1000 g, preferably 0.001 to 100 g, per 1 kg of seed. When the compound of the present invention or a composition containing it is used for foliar application to individual plants, application to the soil surface, injection into the soil or soil irrigation, it is used in an appropriate carrier at an appropriate concentration. Processing may be performed after dilution. When the compound of the present invention or a composition containing it is brought into contact with plant seeds, the plant seeds may be dipped, powdered, sprayed or smeared after being diluted to an appropriate concentration. The amount of the compound of the present invention or the composition containing it in the case of immersion, dressing, spraying or smearing treatment is usually about 0.05 to 50% of the dry plant seed weight as an active ingredient amount, Preferably, 0.1 to 30% is suitable, but it may be appropriately set depending on the form of the composition and the type of plant seed to be treated, and is not limited to these ranges.

Compositions containing the compounds of the present invention may optionally be added to other pesticides such as fungicides, insecticides (including acaricides and nematicides), herbicides, microbial materials, and plant growth regulators. pesticides, disease control agents containing nucleic acids as active ingredients (International Publication No. 2014/062775), soil conditioners or fertilizing substances, and the like.

The method of using the compound of the present invention and other pesticides in combination includes the method of formulating the compound of the present invention and other pesticides into one dosage form and using them, and the method of formulating the compounds of the present invention and other pesticides into separate dosage forms. method of mixing before use, method of using both formulated in separate dosage forms at the same time, or both formulated in separate dosage forms, use either one and then use the other.

Specific ingredients contained in the fungicide that can be mixed and used with the compound of the present invention are exemplified in Group b below, including salts, isomers and N-oxides thereof. However, known disinfectants are not limited to these.

Group b:
b-1: Phenylamide fungicide Phenylamide fungicides include [b-1.1]: benalaxyl, [b-1.2] benalaxyl-M or kiralaxyl, [b -1.3] furalaxyl, [b-1.4] metalaxyl, [b-1.5] metalaxyl-M or mefenoxam, [b-1.6] oxadixyl ( oxadoxyl), [b-1.7] ofurace, and the like.

b-2: Mitotic and Cytotic Inhibitors As mitotic and cytostatic inhibitors, [b-2.1] benomyl, [b-2.2] carbendazim, [b- 2.3] fuberidazole, [b-2.4] thiabendazole, [b-2.5] thiophanate, [b-2.6] thiophanate-methyl, [b- 2.7] diethofencarb, [b-2,8] zoxamide, [b-2.9] ethaboxam, [b-2.10] pencycuron, [b-2. 11] fluopicolide, [b-2.12] phenamacril and the like.

b-3: succinate dehydrogenase inhibitor (SDHI agent)
As succinate dehydrogenase inhibitors (SDHI agents), [b-3.1] benodanil, [b-3.2] benzovindiflupyr, [b-3.3] bixafen ), [b-3.4] boscalid, [b-3.5] carboxin, [b-3.6] fenfuram, [b-3.7] fluopyram , [b-3.8] flutolanil, [b-3.9] fluxapyroxad, [b-3.10] furametpyr, [b-3.11] isofetamide ), [b-3.12] isopyrazam, [b-3.13] mepronil, [b-3.14] oxycarboxin, [b-3.15] penthiopyrad ), [b-3.16] penflufen, [b-3.17] pydiflumetofen, [b-3.18] sedaxane, [b-3.19] thifluzamide ( thifluzamide), [b-3.20]pyraziflumid and the like.

b-4: quinone external inhibitor (QoI agent)
As quinone external inhibitors (QoI agents), [b-4.1] azoxystrobin, [b-4.2] coumoxystrobin, [b-4.3] dimoxist dimoxystrobin, [b-4.4] enoxastrobin, [b-4.5] famoxadone, [b-4.6] fenamidone, [b-4.7 ] fenaminestrobin, [b-4.8] flufenoxystrobin, [b-4.9] fluoxastrobin, [b-4.10] kresoxim-methyl ), [b-4.11] mandestrobin, [b-4.12] metominostrobin, [b-4.13] orysastrobin, [b-4.14] pico xystrobin, [b-4.15] pyraclostrobin, [b-4.16] pyrametostrobin, [b-4.17] pyroxystrobin, [b-4.18] pyribencarb, [b-4.19] triclopyricarb, [b-4.20] trifloxystrobin and the like.

b-5: quinone internal inhibitor (QiI agent)
Quinon internal inhibitors (QiI agents) include [b-5.1] cyazofamid, [b-5.2] amisulbrom and the like.

b-6: Oxidative phosphorylation uncoupling inhibitor As oxidative phosphorylation uncoupling inhibitors, [b-6.1] binapacryl, [b-6.2] meptyldinocap, [ b-6.3] dinocap, [b-6.4] fluazinam and the like.

b-7: Quinone extrinsic stigmatelin-binding subsite inhibitor (QoSI agent)
Quinone extrinsic stigmatelin binding subsite inhibitors (QoSI agents) include [b-7.1]ametoctradin and the like.

b-8: amino acid biosynthesis inhibitors As amino acid biosynthesis inhibitors, [b-8.1] cyprodinil, [b-8.2] mepanipyrim, [b-8.3] pyrimethanil ) and the like.

b-9: Protein biosynthesis inhibitors As protein biosynthesis inhibitors, [b-9.1] streptomycin, [b-9.2] blasticidin-S, [b-9. 3] kasugamycin, [b-9.4] oxytetracycline and the like.

b-10: Signal transduction inhibitor Signal transduction inhibitors include [b-10.1] fenpiclonil, [b-10.2] fludioxonil, [b-10.3] quinoxyfen, [b-10.4] proquinazid, [b-10.5] clozolinate, [b-10.6] dimethachlone, [b-10.7] iprodione, [b -10.8] procymidone, [b-10.9] vinclozolin and the like.

b-11: Lipid and Cell Membrane Biosynthesis Inhibitor As a lipid and cell membrane biosynthesis inhibitor, [b-11.1] edifenphos, [b-11.2] iprobenfos, [b-11.3 ] pyrazophos, [b-11.4] isoprothiolane, [b-11.5] biphenyl, [b-11.6] chloroneb, [b-11.7] dichlorane (dicloran), [b-11.8] quintozene, [b-11.9] tecnazene, [b-11.10] tolclofos-methyl, [b-11.11] etridiazole (echromezol or etridiazole), [b-11.12] iodocarb, [b-11.13] propamocarb, [b-11.14] prothiocarb and the like.

b-12: demethylation inhibitor (DMI agent)
As demethylation inhibitors (DMI agents), [b-12.1] azaconazole, [b-12.2] bitertanol, [b-12.3] bromuconazole, [ b-12.4] cyproconazole, [b-12.5] difenoconazole, [b-12.6] diniconazole, [b-12.7] diniconazole-M ), [b-12.8] epoxiconazole, [b-12.9] etaconazole, [b-12.10] fenarimol, [b-12.11] fenbuconazole (fenbuconazole), [b-12.12] fluquinconazole, [b-12.13] quinconazole, [b-12.14] flusilazole, [b-12.15] flutriafol, [b-12.16] hexaconazole, [b-12.17] imazalil, [b-12.18] imibenconazole, [b- 12.19] ipconazole, [b-12.20] metconazole, [b-12.21] myclobutanil, [b-12.22] nuarimol, [b-12. 23] oxpoconazole, [b-12.24] oxpoconazole fumarate, [b-12.25] pefurazoate, [b-12.26] penconazole ( penconazole), [b-12.27] prochloraz, [b-12.28] propiconazole, [b-12.29] prothioconazole, [b-12.30] pyrifenox, [b-12.31] pyrisoxazole, [b-12.32 ] simeconazole, [b-12.33] tebuconazole, [b-12.34] tetraconazole, [b-12.35] triadimefon, [b-12.36 ] triadimenol, [b-12.37] triflumizole, [b-12.38] triforine, [b-12.39] triticonazole [b- 12.40] mefentrifluconazole, [b-12.41] ipfentrifluconazole and the like.

b-13: Amine fungicides As amine fungicides, [b-13.1] aldimorph, [b-13.2] dodemorph, [b-13.3] fenpropimorph ), [b-13.4] tridemorph, [b-13.5] fenpropidin, [b-13.6] piperalin, [b-13.7] spiroxamine ) and the like.

b-14: 3-keto reductase inhibitor in C4 position demethylation of sterol biosynthesis As a 3-keto reductase inhibitor in C4 position demethylation of sterol biosynthesis, [b-14.1] fenhexamide (fenhexamide), [b-14.2]fenpyrazamine and the like.

b-15: Squalene epoxidase inhibitors of sterol biosynthesis As squalene epoxidase inhibitors of sterol biosynthesis, [b-15.1] pyributicarb, [b-15.2] naftifine, [b -15.3] terbinafine and the like.

b-16: Cell wall biosynthesis inhibitor Cell wall biosynthesis inhibitors include [b-16.1] polyoxins, [b-16.2] dimethomorph, [b-16.3] fullmorph ( flumorph), [b-16.4] pyrimorph, [b-16.5] benthiavalicarb, [b-16.6] benthivalicarb-isopropyl, [b -16.7] iprovalicarb, [b-16.8] mandipropamid, [b-17.9] valifenalate and the like.

b-17: melanin biosynthesis inhibitor melanin biosynthesis inhibitors such as [b-17.1] phthalide or fthalide, [b-17.2] pyroquilone, [b-17.3] tricyclazole (tricyclazole), [b-17.4] carpropamid, [b-17.5] diclocymet, [b-17.6] fenoxanil, [b-17.7] tolprocarb ) and the like.

b-18: Host plant resistance inducer Host plant resistance inducers include [b-18.1] acibenzolar-S-methyl, [b-18.2] probenazole, [b -18.3] tiadinil, [b-18.4] isotianil, [b-18.5] laminarin and the like.

b-19: Dithiocarbamate fungicide Dithiocarbamate fungicides include [b-19.1] mancozeb or manzeb, [b-19.2] maneb, [b-19.3] ] metiram, [b-19.4] propineb, [b-19.5] thiram, [b-19.6] zineb, [b-19.7] ziram (ziram), [b-19.8] ferbam and the like.

b-20: Phthalimide-based fungicides As phthalimide-based fungicides, [b-20.1] captan, [b-20.2] captafol, [b-20.3] folpet ), [b-20.4] fluorofolpet and the like.

b-21: Guanidine fungicide As guanidine fungicides, [b-21.1] guazatin, [b-21.2] iminoctadine, [b-21.3] iminoctadine albesilate (iminoctadine albesilate), [b-21.4] iminoctadine triacetate and the like.

b-22: Multi-point contact active fungicide As multi-point contact active fungicides, [b-22.1] basic copper chloride (copper oxychloride), [b-22.2] cupric hydroxide (copper (II) hydroxide), [b-22.3] basic copper hydroxide sulfate, [b-22.4] organocopper compound, [b-22.5] dodecyl benzene sulfone acid bisethylenediamine copper complex salt [II] (Dodecylbenzenesulphonic acid bisethylenediamine copper [II] salt, DBEDC), [b-22.6] sulfur, [b-22.7] fluoroimide, [b-22. 8] chlorothalonil, [b-22.9] dichlofluanid, [b-22.10] tolylfluanid, [b-22.11] anilazine, [b- 22.12] dithianon, [b-22.13] chinomethionate or quinomethionate, [b-22.14] extract from cotyledons of lupine seedlings (BLAD), and the like.

で表される化合物（国際公開第９８／０４６６０７号参照）、
［ｂ－２３．３８］式（ｓ２）

で表される化合物（国際公開第０８／１４８５７０号参照）、
［ｂ－２３．３９］式（ｓ３）

で表される化合物（国際公開第９２／０１２９７０号参照）、
［ｂ－２３．４０］式（ｓ４）

で表される化合物（国際公開第１２／０８４８１２号参照）、
［ｂ－２３．４１］式（ｓ５）

で表される化合物（ｇｏｕｇｅｒｏｔｉｎ）、
［ｂ－２３．４２］式（ｓ６）

で表される化合物（ｎｉｎｇｎａｎｍｙｃｉｎ）、
［ｂ－２３．４３］式（ｓ７）

で表される化合物（国際公開第１０／１３６４７５号参照）、
［ｂ－２３．４４］式（ｓ８）

で表される化合物（国際公開第１４／０１０７３７号参照）、
［ｂ－２３．４５］式（ｓ９）

で表される化合物（国際公開第１１／０８５０８４号参照）、
［ｂ－２３．４６］式（ｓ１０）

で表される化合物（国際公開第１１／１３７００２号参照）、
［ｂ－２３．４７］式（ｓ１１）

で表される化合物（国際公開第１３／１６２０７２号参照）、
［ｂ－２３．４８］式（ｓ１２）

で表される化合物（国際公開第０８／１１０３１３号参照）、
［ｂ－２３．４９］式（ｓ１３）

で表される化合物（国際公開第０９／１５６０９８号参照）、
［ｂ－２３．５０］式（ｓ１４）

で表される化合物（国際公開第１２／０２５５５７号参照）、
［ｂ－２３．５１］式（ｓ１５）

で表される化合物（国際公開第１４／００６９４５号参照）、
［ｂ－２３．５２］式（ｓ１６）

［式中、Ａ３は、水素原子、ハロゲン原子、Ｃ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、またはシアノ基を表し、Ａ４は、水素原子、Ｃ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、またはＣ３～Ｃ８のシクロアルキル基を表す。］で表される化合物（国際公開第１４／０９５６７５号参照）、
［ｂ－２３．５３］式（ｓ１７）

［式中、ｍ１は、０～３の整数を表し、Ａ５およびＡ６は、それぞれ独立していて、ハロゲン原子、またはＣ１～Ｃ６のアルキル基を表し、Ａ７およびＡ８は、それぞれ独立していて、ハロゲン原子、またはＣ１～Ｃ６のアルコキシ基を表し、ｍ１が２以上の場合、２以上のＡ７は、それぞれ独立した置換基を表し、同一または異なっていてよい。］で表される化合物（国際公開第０９／１３７５３８号、国際特許第０９／１３７６５１号参照）、
［ｂ－２３．５４］式（ｓ１８）

［式中、Ａ９およびＡ１０は、それぞれ独立していて、水素原子、またはハロゲン原子を表し、Ａ１１は、ハロゲン原子を表し、Ａ１２は、ハロゲン原子、またはＣ１～Ｃ６のアルキル基を表し、Ａ１３は、ハロゲン原子、シアノ基、Ｃ１～Ｃ６のアルキル基、またはＣ１～Ｃ６のアルコキシ基を表す。］で表される化合物（国際公開第１２／０３１０６１号参照）、
［ｂ－２３．５５］式（ｓ１９）

［式中、ｍ２は、０～６の整数を表し、Ａ１４およびＡ１５は、それぞれ独立していて、ハロゲン原子、シアノ基、またはＣ１～Ｃ６のアルキル基を表し、Ａ１６は、水素原子、ハロゲン原子、またはＣ１～Ｃ６のアルコキシ基を表し、Ａ１７は、ハロゲン原子、またはＣ１～Ｃ６のアルコキシ基を表し、ｍ２が２以上の場合、２以上のＡ１７は、それぞれ独立した置換基を表し、同一または異なっていてよい。］で表される化合物（国際公開第０５／１２１１０４号参照）、
［ｂ－２３．５６］式（ｓ２０）

［式中、Ａ１８およびＡ１９は、それぞれ独立していて、ハロゲン原子、シアノ基、またはＣ１～Ｃ６のアルキル基を表し、Ａ２０、Ａ２１およびＡ２２は、それぞれ独立していて、水素原子、ハロゲン原子、またはＣ１～Ｃ６のアルコキシ基を表す。］で表される化合物（国際公開第０７／０６６６０１号参照）、
［ｂ－２３．５７］式（ｓ２１）

［式中、Ａ２３およびＡ２４は、それぞれ独立していて、水素原子、ハロゲン原子、Ｃ１～Ｃ６のアルキル基、またはＣ３～Ｃ８のシクロアルキル基を表し、Ｘは、酸素原子または硫黄原子を表す。］で表される化合物（国際公開第０７／０８７９０６号、国際特許第０９／０１６２２０号、国際特許第１０／１３０７６７号参照）、
［ｂ－２３．５８］式（ｓ２２）

［式中、ｍ３は、０～５の整数を表し、Ａ２５は、ハロゲン原子、Ｃ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、またはＣ３～Ｃ８のシクロアルキル基を表し、ｍ３が２以上の場合、２以上のＡ２５は、それぞれ独立した置換基を表し、同一または異なっていてよい。］で表される化合物（国際公開第１３／０９２２２４号参照）、
［ｂ－２３．５９］式（ｓ２３）

［式中、Ａ２６は、水素原子、またはハロゲン原子を表し、Ｖ１およびＶ２は、それぞれ独立していて、酸素原子、または硫黄原子を表す。］で表される化合物（国際公開第１２／０２５４５０号参照）、
［ｂ－２３．６０］式（ｓ２４）または式（ｓ２５）

［式中、ｍ４は、０～５の整数を表し、Ａ２７は、Ｃ１～Ｃ６のアルキル基を表し、Ａ２８は、ハロゲン原子、シアノ基、Ｃ１～Ｃ６のアルキル基、またはＣ１～Ｃ６のハロアルキル基を表し、ｍ４が２以上の場合、２以上のＡ２８は、それぞれ独立した置換基を表し、同一または異なっていてよく、Ａ２９は、Ｃ１～Ｃ６のアルキル基、Ｃ２～Ｃ６のアルケニル基、またはＣ３～Ｃ６のアルキニル基を表す。］で表される化合物（国際公開第１３／０３７７１７号参照）、
［ｂ－２３．６１］式（ｓ２６）または式（ｓ２７）

［式中、ｍ５は、０～５の整数を表し、Ａ３０は、Ｃ１～Ｃ６のアルキル基を表し、Ａ３１は、ハロゲン原子、シアノ基、Ｃ１～Ｃ６のアルキル基、またはＣ１～Ｃ６のハロアルキル基を表し、ｍ５が２以上の場合、２以上のＡ３１は、それぞれ独立した置換基を表し、同一または異なっていてよく、Ａ３２は、Ｃ１～Ｃ６のアルキル基、Ｃ２～Ｃ６のアルケニル基、またはＣ３～Ｃ６のアルキニル基を表す。］で表される化合物（国際公開第１３／０３７７１７号参照）、
［ｂ－２３．６２］式（ｓ２８）

［式中、Ａ３３、Ａ３４、Ａ３５およびＡ３６は、それぞれ独立していて、水素原子、またはハロゲン原子を表し、Ａ３７は、水素原子、アセチル基、またはベンゾイル基を表す。］で表される化合物（国際公開第０６／０３１６３１号、国際特許第１０／０６９８８２号参照）、
［ｂ－２３．６３］式（ｓ２９）

［式中、Ａ３８は、Ｃ１～Ｃ６のアルキル基、またはＣ１～Ｃ６のハロアルキル基を表し、Ａ３９およびＡ４０は、それぞれ独立していて、水素原子、またはハロゲン原子を表す。］で表される化合物（国際公開第１４／０４３３７６号参照）、
［ｂ－２３．６４］式（ｓ３０）

［式中、Ａ４１は、水素原子、水硫基（－ＳＨ）、チオシアン酸基（－ＳＣＮ）、またはＣ１～Ｃ６のアルキルチオ基を表し、Ａ４２、Ａ４３、Ａ４４およびＡ４５は、それぞれ独立していて、水素原子、またはハロゲン原子を表す。］で表される化合物（国際公開第０９／０７７４４３号参照）、
［ｂ－２３．６５］式（ｓ３１）または式（ｓ３２）

［式中、Ａ４６は、水素原子、またはハロゲン原子を表し、Ａ４７は、Ｃ１～Ｃ６のアルキル基を表し、Ａ４８は、ハロゲン原子を表す。］で表される化合物（国際公開第１１／０７０７７１号参照）、
［ｂ－２３．６６］式（ｓ３３）

［式中、Ａ４９、Ａ５０およびＡ５１は、それぞれ独立していて、水素原子、またはハロゲン原子を表す。］で表される化合物（国際公開第１１／０８１１７４号参照）等が挙げられる。b-23: Other fungicides Other fungicides include [b-23.1] dichlobentiazox, [b-23.2] fenpicoxamide, [b-23.3 ] dipymetitrone, [b-23.4] bupirimate, [b-23.5] dimethirimol, [b-23.6] ethirimol, [b-23.7] acetic acid triphenyltin acetate, [b-23.8]triphenyltin chloride, [b-23.9]fentin hydroxide, [b-23.10]oxolinic acid (oxolinic acid), [b-23.11] hymexazol, [b-23.12] octhilinone, [b-23.13] fosetyl, [b-23.14] phosphorus phosphorous acid, [b-23.15] sodium phosphite, [b-23.16] ammonium phosphite, [b-23.17] potassium phosphate, [b-23.18] tecloftalam, [b-23.19] triazoxide, [b-23.20] flusulfamide, [b-23 .21] diclomezine, [b-23.22] silthiofam, [b-23.23] diflumetrim, [b-23.24] methasulfocarb, [b-23 .25] cyflufenamide, [b-23.26] metrafenone, [b-23.27] pyriofenone, [b-23.28] dodine, [b-23.29 ] flutianil, [b-23.30] ferimzone, [b-23.31] oxathiapiprolin, [b-23.32] tebufloquin, [b-23.33] picarbutrazox, [b-23.34] validamycins, [b-23.35] cymoxanil ), [b-23.36] quinofumelin,
[b-23.37] Formula (s1)

A compound represented by (see WO 98/046607),
[b-23.38] Formula (s2)

A compound represented by (see WO 08/148570),
[b-23.39] Formula (s3)

A compound represented by (see WO 92/012970),
[b-23.40] Expression (s4)

A compound represented by (see WO 12/084812),
[b-23.41] Formula (s5)

A compound represented by (gougerotin),
[b-23.42] Expression (s6)

A compound represented by (ningnanmycin),
[b-23.43] Expression (s7)

A compound represented by (see WO 10/136475),
[b-23.44] Formula (s8)

A compound represented by (see WO 14/010737),
[b-23.45] Formula (s9)

A compound represented by (see WO 11/085084),
[b-23.46] Formula (s10)

A compound represented by (see WO 11/137002),
[b-23.47] Formula (s11)

A compound represented by (see WO 13/162072),
[b-23.48] Formula (s12)

A compound represented by (see WO 08/110313),
[b-23.49] Formula (s13)

A compound represented by (see WO 09/156098),
[b-23.50] Formula (s14)

A compound represented by (see WO 12/025557),
[b-23.51] Formula (s15)

A compound represented by (see WO 14/006945),
[b-23.52] Expression (s16)

[Wherein, A3 represents a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a cyano group; A4 represents a hydrogen atom, a C1-C6 alkyl group, a C1-C6 It represents a haloalkyl group or a C3-C8 cycloalkyl group. ] (see WO 14/095675),
[b-23.53] Expression (s17)

[Wherein, m1 represents an integer of 0 to 3, A5 and A6 each independently represent a halogen atom or a C1 to C6 alkyl group, A7 and A8 each independently represents a halogen atom or a C1-C6 alkoxy group, and when m1 is 2 or more, two or more A7 represent independent substituents and may be the same or different. ] (see International Publication No. 09/137538, International Patent No. 09/137651),
[b-23.54] Formula (s18)

[Wherein, A9 and A10 each independently represent a hydrogen atom or a halogen atom, A11 represents a halogen atom, A12 represents a halogen atom or a C1-C6 alkyl group, and A13 represents , a halogen atom, a cyano group, a C1-C6 alkyl group, or a C1-C6 alkoxy group. ] (see WO 12/031061),
[b-23.55] Formula (s19)

[In the formula, m2 represents an integer of 0 to 6, A14 and A15 each independently represents a halogen atom, a cyano group, or a C1 to C6 alkyl group, and A16 represents a hydrogen atom, a halogen atom, , or represents a C1-C6 alkoxy group, A17 represents a halogen atom or a C1-C6 alkoxy group, and when m2 is 2 or more, 2 or more A17 each represent an independent substituent, the same or can be different. ] (see WO 05/121104),
[b-23.56] formula (s20)

[Wherein, A18 and A19 each independently represent a halogen atom, a cyano group, or a C1-C6 alkyl group; A20, A21 and A22 each independently represent a hydrogen atom, a halogen atom, or represents a C1-C6 alkoxy group. ] (see WO 07/066601),
[b-23.57] formula (s21)

[In the formula, A23 and A24 each independently represent a hydrogen atom, a halogen atom, a C1-C6 alkyl group, or a C3-C8 cycloalkyl group, and X represents an oxygen atom or a sulfur atom. ] (see International Publication No. 07/087906, International Patent No. 09/016220, International Patent No. 10/130767),
[b-23.58] formula (s22)

[Wherein, m3 represents an integer of 0 to 5, A25 is a halogen atom, a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group, or represents a C3-C8 cycloalkyl group, and when m3 is 2 or more, two or more A25 represent independent substituents and may be the same or different. ] (see WO 13/092224),
[b-23.59] formula (s23)

[In the formula, A26 represents a hydrogen atom or a halogen atom, and V1 and V2 each independently represent an oxygen atom or a sulfur atom. ] (see WO 12/025450),
[b-23.60] Formula (s24) or Formula (s25)

[Wherein, m4 represents an integer of 0 to 5, A27 represents a C1 to C6 alkyl group, A28 represents a halogen atom, a cyano group, a C1 to C6 alkyl group, or a C1 to C6 haloalkyl group When m4 is 2 or more, 2 or more A28 each represent an independent substituent which may be the same or different, and A29 is a C1 to C6 alkyl group, a C2 to C6 alkenyl group, or a C3 represents an alkynyl group of ~C6. ] (see WO 13/037717),
[b-23.61] formula (s26) or formula (s27)

[Wherein, m5 represents an integer of 0 to 5, A30 represents a C1 to C6 alkyl group, A31 represents a halogen atom, a cyano group, a C1 to C6 alkyl group, or a C1 to C6 haloalkyl group When m5 is 2 or more, 2 or more A31 each represent an independent substituent which may be the same or different, and A32 is a C1 to C6 alkyl group, a C2 to C6 alkenyl group, or a C3 represents an alkynyl group of ~C6. ] (see WO 13/037717),
[b-23.62] formula (s28)

[In the formula, A33, A34, A35 and A36 each independently represent a hydrogen atom or a halogen atom, and A37 represents a hydrogen atom, an acetyl group or a benzoyl group. ] (see International Publication No. 06/031631, International Patent No. 10/069882),
[b-23.63] formula (s29)

[In the formula, A38 represents a C1-C6 alkyl group or a C1-C6 haloalkyl group, and A39 and A40 each independently represent a hydrogen atom or a halogen atom. ] (see WO 14/043376),
[b-23.64] formula (s30)

[In the formula, A41 represents a hydrogen atom, a hydrogen sulfur group (-SH), a thiocyanate group (-SCN), or a C1-C6 alkylthio group, and A42, A43, A44 and A45 are each independently , a hydrogen atom, or a halogen atom. ] (see WO 09/077443),
[b-23.65] Formula (s31) or Formula (s32)

[In the formula, A46 represents a hydrogen atom or a halogen atom, A47 represents a C1 to C6 alkyl group, and A48 represents a halogen atom. ] (see WO 11/070771),
[b-23.66] formula (s33)

[In the formula, A49, A50 and A51 each independently represent a hydrogen atom or a halogen atom. ] (see International Publication No. 11/081174) and the like.

Specific ingredients contained in pesticides that can be used in admixture with the compounds of the present invention are exemplified in Group c below, including salts, isomers and N-oxides thereof. However, known insecticides are not limited to these.

Group c:
c-1: Carbamate Acetylcholinesterase (AChE) Inhibitors As carbamate acetylcholinesterase (AChE) inhibitors, [c-1.1] phosphocarb, [c-1.2] alanycarb, [c -1.3] butocarboxim, [c-1.4] butoxycarboxim, [c-1.5] thiodicarb, [c-1.6] thiofanox ), [c-1.7] aldicarb, [c-1.8] bendiocarb, [c-1.9] benfuracarb, [c-1.10] carbaryl, [c-1.11] carbofuran, [c-1.12] carbosulfan, [c-1.13] ethiofencarb, [c-1.14] fenobucarb, [c-1.15] formetanate, [c-1.16] furatiocarb, [c-1.17] isoprocarb, [c-1.18] methiocarb, [c -1.19] methomyl, [c-1.20] oxamyl, [c-1.21] pirimicarb, [c-1.22] propoxur, [c-1 .23] trimethacarb, [c-1.24] XMC (3,5-xylyl methylcarbamate), [c-1.25] allyxycarb, [c-1.26] aldoxycarb , [c-1.27] bufencarb, [c-1.28] butacarb, [c-1.29] carbanolate, [c-1.30] metolcarb, [ c-1.31] xylylcarb, [c-1.32] phenothiocarb, [c-1.33] xylylcarb, [c-1.34] bendiocarb and bendiocarb.

c-2: Organophosphorus acetylcholinesterase (AChE) inhibitors Organophosphate acetylcholinesterase (AChE) inhibitors include [c-2.1] acephate, [c-2.2] azamethiphos, [c-2.3] azinphos-methyl, [c-2.4] azinphos-ethyl, [c-2.5] ethephon, [c-2.6 ] cadusafos, [c-2.7] chlorethoxyfos, [c-2.8] chlorfenvinphos, [c-2.9] chlormephos, [c- 2.10] chlorpyrifos, [c-2.11] chlorpyrifos-methyl, [c-2.12] coumaphos, [c-2.13] cyanophos, [ c-2.14] demeton-S-methyl, [c-2.15] diazinon, [c-2.16] dichlofenthion, [c-2.17] Dichlorvos, [c-2.18] dicrotophos, [c-2.19] dimethoate, [c-2.20] dimethylvinphos, [c-2.21] disulfoton, [c-2.22] O-ethyl O-4-nitrophenyl phenylphosphonothioate, [c-2.23] ethion, [ c-2.24] ethoprophos, [c-2.25] famphur, [c-2.26] fenamiphos, [c-2.27] fenitrothion, [c- 2.28] fenthion, [c-2.29] fosthiazate, [c-2.30] heptenophos, [c-2.31] isofenphos- isofenphos-methyl, [c-2.32] Isocarbophos, [c-2.33] isoxathion, [c-2.34] malathion, [c-2.35] mecarbam, [c-2.36] methamidophos, [c-2.37] methidathion, [c-2.38] mevinphos, [c-2.39] monocrotophos (monocrotophos), [c-2.40] naled, [c-2.41] omethoate, [c-2.42] oxydemeton-methyl, [c-2.43 ] parathions, [c-2.44] parathion-methyl, [c-2.45] phenthoate, [c-2.46] phorate, [c-2 .47] phosalone, [c-2.48] phosmet, [c-2.49] phosphamidon, [c-2.50] phoxim, [c-2.51 ] pirimiphos-methyl, [c-2.52] profenofos, [c-2.53] propetamphos, [c-2.54] prothiofos, [c-2 .55] pyraclofos, [c-2.56] pyridaphenthion, [c-2.57] quinalphos, [c-2.58] sulfotep, [c-2.59 ] Tebupirimfos, [c-2.60] Temephos, [c-2.61] Terbufos, [c-2.62] Thiometon, [c-2.63] Triazophos (triazophos), [c-2.64] trichlorfon, [c-2.65] vamidothion, [c-2.66] chlorothion, [c-2.67] bromo bromfenvinfos, [c-2.68] bromophos, [c-2.69] bromophos-ethyl, [c-2.70] butathiofos, [c-2. 71] carbophenothion, [c-2.72] chlorphoxim, [c-2.73] sulprofos, [c-2.74] diamidafos, [c-2. 75] tetrachlorvinphos, [c-2.76] propaphos, [c-2.77] mesulfenfos, [c-2.78] dioxabenzofos, [ c-2.79] etrimfos, [c-2.80] oxydeprofos, [c-2.81] formothion, [c-2.82] fensulfothion, [ c-2.83] isazofos, [c-2.84] imicyafos, [c-2.85] isamidofos, [c-2.86] thionazin, [c- 2.87] fosthietan and the like.

c-3: GABAergic chloride ion channel blocker As GABAergic chloride ion channel blockers, [c-3.1] chlordane, [c-3.2] endosulfan, [c-3.3 ] lindane, [c-3.4] dienochlor, [c-3.5] ethiprole, [c-3.6] fipronil, [c-3.7] aceto and acetoprole.

c-4: Sodium channel modulators Sodium channel modulators include [c-4.1] acrinathrin, [c-4.2] allethrin [(1R)-isomer] (allethrin [(1R)-isomer]), [c-4.3] bifenthrin, [c-4.4] bioallethrin, [c-4.5] bioallethrin S-cyclopentenyl isomer, [c- 4.6] bioresmethrin, [c-4.7] cycloprothrin, [c-4.8] cyfluthrin, [c-4.9] beta-cyfluthrin , [c-4.10] cyhalothrin, [c-4.11] gamma-cyhalothrin, [c-4.12] lambda-cyhalothrin, [c-4. 13] cypermethrin, [c-4.14] alpha-cypermethrin, [c-4.15] beta-cypermethrin, [c-4.16] ceta - cypermethrin (theta-cypermethrin), [c-4.17] zeda-cypermethrin (zeta-cypermethrin), [c-4.18] cyphenothrin [(1R)-trans-isomer] (cyphenothrin [(1R) -trans-isomer]), [c-4.19] deltamethrin, [c-4.20] empenthrin [(EZ)-(1R)-isomer] (empenthrin [(EZ)-(1R)-isomer ]), [c-4.21] esfenvalerate, [c-4.22] ethofenprox, [c-4.23] fenpropathrin, [c-4. 24] fenvalerate, [c-4.25] flucythrinate, [c-4.26] flumethrin rin), [c-4.27] tau-fluvalinate, [c-4.28] halfenprox, [c-4.29] imiprothrin, [c-4 .30] methothrin, [c-4.31] metofluthrin, [c-4.32] epsilon-metofluthrin, [c-4.33] momfluorothrin, [c-4.34] epsilon-momfluorothrin, [c-4.35] permethrin, [c-4.36] phenothrin [(1R)-trans-isomer] (phenothrin [ (1R)-trans-isomer]), [c-4.37] prallethrin, [c-4.38] resmethrin, [c-4.39] kadethrin, [c-4 .40] silafluofen, [c-4.41] tefluthrin, [c-4.42] tetramethrin, [c-4.43] tetramethrin [(1R)-isomer] (tetramethrin [ (1R)-isomer]), [c-4.44] tralomethrin, [c-4.45] transfluthrin, [c-4.46] ZXI8901 (3-(4-bromophenoxy) phenyl]-cyanomethyl 4-(difluoromethyl)-α-(1-methylethyl)benzeneacetate), [c-4.47] biopermethrin, [c-4.48] furamethrin, [c-4. 49] profluthrin, [c-4.50] flubrocythrinate, [c-4.51] dimefluthrin, [c-4.52] DDT (dichloro-diphenyl-trichloroethane), [c-4.53] methoxychlor , [c-4.54] phenothrin, [c-4.55] fluvalinate and the like.

c-5: Nicotinic acetylcholine receptor (nAChR) competitive modulators As nicotinic acetylcholine receptor (nAChR) competitive modulators, [c-5.1] acetamiprid, [c-5.2] clothianidin ), [c-5.3] dinotefuran, [c-5.4] imidacloprid, [c-5.5] nitenpyram, [c-5.6] thiacloprid, [c-5.7] thiamethoxam, [c-5.8] nicotine, [c-5.9] nicotine sulfate, [c-5.10] sulfoxaflor, [c-5.11] flupyradifurone, [c-5.12] triflumezopyrim and the like.

c-6: Nicotinic acetylcholine receptor (nAChR) allosteric modulator Nicotinic acetylcholine receptor (nAChR) allosteric modulators such as [c-6.1] spinosad, [c-6.2] spinetoram are mentioned.

c-7: Glutamatergic chloride channel (GluCl) allosteric modulators As glutamatergic chloride channel (GluCl) allosteric modulators, [c-7.1] abamectin, [c-7.2] emamectin benzoate salt (emamectin benzoate), [c-7.3] lepimectin, [c-7.4] milbemectin and the like.

c-8: Juvenile Hormone Analogs As juvenile hormone analogs, [c-8.1] hydroprene, [c-8.2] kinoprene, [c-8.3] methoprene ), [c-8.4]fenoxycarb, [c-8.5]pyriproxyfen and the like.

c-9: Non-specific (multi-site) inhibitor Non-specific (multi-site) inhibitors include [c-9.1] methyl bromide, [c-9.2] chloropicrin , [c-9.3] cryolite, [c-9.4] sulfuryl fluoride, [c-9.5] borax, [c-9.6] boron Boric acid, [c-9.7] disodium octaborate, [c-9.8] sodium metaborate [c-9.9] tartar emetic), [c-9.10] dazomet, [c-9.11] metam, [c-9.12] carbam sodium and the like.

c-10: Chordone TRPV Channel Modulator Chordone TRPV channel modulators include [c-10.1] pymetrozine, [c-10.2] pyrifluquinazon and the like.

c-11: Mites Growth Inhibitors As mites growth inhibitors, [c-11.1] clofentezine, [c-11.2] diflovidazin, [c-11.3] hexythiazox (hexythiazox), [c-11.4] etoxazole and the like.

c-12: Mitochondrial ATP Synthase Inhibitor As a mitochondrial ATP synthase inhibitor, [c-12.1] diafenthiuron, [c-12.2] azocyclotin, [c-12. 3] cyhexatin, [c-12.4] fenbutatin oxide, "c-12.5" propargite, "c-12.6" tetradifon and the like .

c-13: Oxidative phosphorylation uncoupling agent that disrupts the proton gradient As oxidative phosphorylation uncoupling agents that disrupt the proton gradient, [c-13.1] chlorfenapyl, [c-13.2] DNOC (dinitro-ortho-cresol), [c-13.3] binapacryl, [c-13.4] sulfluramid and the like.

c-14: Nicotinic acetylcholine receptor (nAChR) channel blocker As nicotinic acetylcholine receptor (nAChR) channel blockers, [c-14.1] bensultap, [c-14.2] cartap hydrochloride hydrochloride), [c-14.3] thiocyclam, [c-14.4] monosultap and the like.

c-15: chitin biosynthesis inhibitor type 0
As chitin biosynthesis inhibitor type 0, [c-15.1] bistrifluron, [c-15.2] chlorfluazuron, [c-15.3] diflubenzuron, [c-15.4] flucycloxuron, [c-15.5] flufenoxuron, [c-15.6] hexaflumuron, [c-15.7] lufenuron, [c-15.8] novaluron, [c-15.9] noviflumuron, [c-15.10] teflubenzuron, [c-15.11] triflumuron ( triflumuron) and the like.

c-16: chitin biosynthesis inhibitor type 1
Chitin biosynthesis inhibitor type 1 includes [c-16.1] buprofezin and the like.

c-17: Moulting Inhibitor of Diptera Insect Moulting inhibitor of Diptera includes [c-17.1] cyromazine and the like.

c-18: molting hormone (ecdysone) receptor agonists [c-18.1] chromafenozide, [c-18.2] halofenozide, [c-18] as molting hormone (ecdysone) receptor agonists .3] methoxyfenozide, [c-18.4] tebufenozide and the like.

c-19: Octopamine Receptor Agonists Examples of octopamine receptor agonists include [c-19.1] amitraz and the like.

c-20: Mitochondrial Electron Transport System Complex III Inhibitors As mitochondrial electron transport system complex III inhibitors, [c-20.1] hydramethylnon, [c-20.2] acequinocyl, [c-20.3] fluacrypyrim, [c-20.4] bifenazate and the like.

c-21: mitochondrial electron transport chain complex I inhibitor (METI)
As mitochondrial electron transport chain complex I inhibitors (METI), [c-21.1] fenazaquin, [c-21.2] fenpyroximate, [c-21.3] pyridaben, [c-21.4] pyrimidifen, [c-21.5] tebufenpyrad, [c-21.6] tolfenpyrad, [c-21.7] rotenone and the like be done.

c-22: Voltage-gated sodium channel blockers Voltage-gated sodium channel blockers include [c-22.1] indoxacarb, [c-22.2] metaflumizone and the like.

c-23: Acetyl-CoA carboxylase inhibitors As acetyl-CoA carboxylase inhibitors, [c-23.1] spirodiclofen, [c-23.2] spiromesifen, [c-23.3 ] and spirotetramat.

c-24: Mitochondrial electron transport system complex IV inhibitor Mitochondrial electron transport system complex IV inhibitors include [c-24.1] aluminum phosphide, [c-24.2] calcium phosphide ( calcium phosphide), [c-24.3] phosphine, [c-24.4] zinc phosphide, [c-24.5] calcium cyanide, [c -24.6] sodium cyanide, [c-24.7] sodium cyanide and the like.

c-25: Mitochondrial electron transport system complex II inhibitor Mitochondrial electron transport system complex II inhibitors include [c-25.1] cyenopyrafen, [c-25.2] cyflumetofen, [c -25.3] pyflubumide and the like.

c-26: ryanodine receptor modulators As ryanodine receptor modulators, [c-26.1] chlorantraniliprole, [c-26.2] cyantraniliprole, [c-26. 3] Flubendiamide and the like.

c-27: Unspecified target-site-unspecified chordotonal organ modulator Examples of target-site-unspecified chordotonal organ modulators include [c-27.1] flonicamid and the like.

で表される化合物（国際公開第１０／０５１９２６号参照）、
［ｃ－２８．１１９］式（ｓ３５）

で表される化合物（国際公開第１３／１１５３９１号参照）、
［ｃ－２８．１２０］式（ｓ３６）

で表される化合物（国際公開第１２／０２９６７２号参照）、
［ｃ－２８．１２１］式（ｓ３７）

で表される化合物（国際公開第０６／０５６１０８号参照）、
［ｃ－２８．１２２］式（ｓ３８）

で表される化合物（国際公開第１４／０５３４５０号、国際特許第１５／１４４６８３号参照）、
［ｃ－２８．１２３］式（ｓ３９）

で表される化合物（国際公開第１４／０５３４５０号、国際特許第１５／１４４６８３号参照）、
［ｃ－２８．１２４］式（ｓ４０）

で表される化合物（国際公開第１４／０５３４５０号、国際特許第１５／１４４６８３号参照）、
［ｃ－２８．１２５］式（ｓ４１）

［式中、ｍ６は、０～２の整数を表す。］で表される化合物（国際公開第１０／１２９４９７号参照）、
［ｃ－２８．１２６］式（ｓ４２）

［式中、ｍ７は、０～２の整数を表す。］で表される化合物（国際公開第１１／１５２３２０号参照）、
［ｃ－２８．１２７］式（ｓ４３）

［式中、ｍ８は、０～２の整数を表す。］で表される化合物（特開平２７―１６０８１３号公報参照）、
［ｃ－２８．１２８］式（ｓ４４）

［式中、Ａ５２は、水素原子、またはフッ素原子を表す。］で表される化合物（国際公開第１１／１３４９６４号、国際特許第１４／００５９８２号参照）、
［ｃ－２８．１２９］式（ｓ４５）

［式中、ｍ９は、０～２の整数を表し、Ａ５３は、フッ素原子、または塩素原子を表す。］で表される化合物（国際公開第１５／０２５８２６号参照）、
［ｃ－２８．１３０］式（ｓ４６）

［式中、Ｖ３は、窒素原子、炭素原子、またはＣ－Ｆを表し、Ｖ４およびＶ５は、それぞれ独立していて、窒素原子、または炭素原子を表す。］で表される化合物（国際公開第１１／１３４９６４号、国際公開第１４／００５９８２号参照）、
［ｃ－２８．１３１］式（ｓ４７）

［式中、Ａ５４は、水素原子、メチル基、メトキシ基、またはエトキシ基を表し、Ａ５５は、塩素原子、またはメチル基を表し、Ａ５６は、メチル基、またはエチル基を表す。］で表される化合物（国際公開第０９／０４９８５１号参照）、
［ｃ－２８．１３２］式（ｓ４８）

［式中、Ａ５７は、水素原子、フッ素原子、または塩素原子を表し、Ａ５８は、

からなる群から選択される１種の部分構造を表す。］で表される化合物（国際公開第１１／０６７２７２号参照）、
［ｃ－２８．１３３］式（ｓ４９）

［式中、Ａ５９は、水素原子、フッ素原子、または塩素原子を表し、Ａ６０は、

からなる群から選択される部分構造を表す。］で表される化合物（国際公開第１０／０９０３４４号参照）、
［ｃ－２８．１３４］式（ｓ５０）

［式中、ｍ１０は、０～２の整数を表し、Ａ６１は、トリフルオロメチル基、トリフルオロメチルチオ基、トリフルオロメチルスルフィニル基、またはトリフルオロメチルスルホニル基を表し、Ａ６２は、水素原子、またはトリフルオロメチル基を表し、Ｖ６は、窒素原子、または炭素原子を表し、Ｖ７は、酸素原子、またはＮ－メチル基を表す。］で表される化合物（国際公開第１４／１０４４０７号参照）、
［ｃ－２８．１３５］式（ｓ５１）

［式中、Ａ６３は、水素原子、またはフッ素原子を表し、アミド基は４位、または５位に結合し、Ａ６４は、

からなる群から選択される部分構造を表す。］で表される化合物（国際公開第１５／０３８５０３号、国際特許第１６／１４４３５１号、国際特許第１６／１４４６７８号参照）、
［ｃ－２８．１３６］式（ｓ５２）

［式中、Ａ６５は、水素原子、Ｃ１～Ｃ６のアルキル基、またはＣ１～Ｃ６のハロアルキル基を表し、Ａ６６は、水素原子、ハロゲン原子、またはＣ１～Ｃ６のアルキル基を表し、Ａ６７およびＡ６８は、それぞれ独立していて、水素原子、シアノ基で適宜置換されてもよいＣ１～Ｃ６のアルキル基、メトキシ基で適宜置換されてもよいアルキル基、エトキシ基で適宜置換されてもよいアルキル基、またはＣ３～Ｃ８のシクロアルキル基を表し、
Ａ６９は、水素原子、シアノ基、シアノ基で適宜置換されてもよいＣ１～Ｃ６のハロアルキル基、Ｃ１～Ｃ６のアルキル基、またはＣ３～Ｃ８のシクロアルキル基を表す。］で表される化合物（国際公開第１２／１４３３１７号、国際特許第１６／０１６３６９号参照）、
［ｃ－２８．１３７］式（ｓ５３）または式（ｓ５４）

［式中、Ａ７０は、メチル基、エチル基、イソプロピル基、２，２，２－トリフルオロエチル基、またはフェニル基を表し、Ａ７１は、

からなる群から選択される部分構造を表し、Ａ７２は、

からなる群から選択される部分構造を表し、Ｖ８は、酸素原子、硫黄原子、－ＣＨ_２－、または－ＣＨ_２ＣＨ_２－を表す。］で表される化合物（国際公開第１４／１６７０８４号、国際特許第１６／０５５４３１号参照）、
［ｃ－２８．１３８］式（ｓ５５）

［式中、ｍ１１は、０～１の整数を表し、Ａ７３は、塩素原子、臭素原子、メチル基、またはトリフルオロメチル基を表し、Ａ７４は、水素原子、塩素原子、臭素原子、シアノ基、またはトリフルオロメチル基表し、Ａ７５は、水素原子、塩素原子または臭素原子を表し、Ａ７６およびＡ７７は、それぞれ独立していて、Ｃ１～Ｃ６のアルキル基、またはＣ３～Ｃ８のシクロアルキル基を表し、Ａ７８は、塩素原子、臭素原子、シアノ基、ニトロ基、ジフルオロメチル基、またはトリフルオロメチル基を表す。］で表される化合物（国際公開第１３／０２４００９号参照）、
［ｃ－２８．１３９］式（ｓ５６）

［式中、Ａ７９、Ａ８０、Ａ８１およびＡ８２は、それぞれ独立していて、水素原子、ハロゲン原子、Ｃ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ１～Ｃ６のアルコキシ基、またはＣ３～Ｃ８のシクロアルコキシ基を表す。］で表される化合物（国際公開第１２／０２７５２１号参照）、
［ｃ－２８．１４０］式（ｓ５７）

［式中、ｍ１２は、０～２の整数を表し、Ａ８３は、水素原子、またはフッ素原子を表し、Ａ８４は、

からなる群から選択される部分構造を表す。］で表される化合物（国際公開第１３／１６２７１５号参照）、
［ｃ－２８．１４１］アシノナピル（ａｃｙｎｏｎａｐｙｒ）、
［ｃ－２８．１４２］式（ｓ５９）

［Ａ９０は、ハロゲン原子、Ｃ１～Ｃ６のアルキル基、またはＣ１～Ｃ６のハロアルキル基を表し、Ａ９１は、Ｃ１～Ｃ６のハロアルキル基を表し、Ａ９２およびＡ９３は、それぞれ独立していて、水素原子、Ｃ１～Ｃ６のアルキル基、アセチル基、プロピオノイル基、メタンスルホニルエチル基、メトキシカルボニル基、またはエトキシカルボニル基を表し、Ａ９４およびＡ９５は、それぞれ独立していて、水素原子、Ｃ１～Ｃ６のアルキル基、またはＣ１～Ｃ６のハロアルキル基を表す。］で表される化合物（国際公開第１２／１６４６９８号参照）等が挙げられる。c-28: Other insecticides Other insecticides such as [c-28.1] azadirachtin, [c-28.2] benzoximate, [c-28.3] phenisobromo phenisobromolate, [c-28.4]chinomethionate, [c-28.5]dicofol, [c-28.6]pyridalyl, [c-28.7]bromopropoxy bromopropylate, [c-28.8] triazamate, [c-28.9] dicyclanil, [c-28.10] dinobuton, [c-28.11] dinocap ( dinocap), [c-28.12] hydrogen cyanide, [c-28.13] methyl iodide, [c-28.14] karanjin, [c-28.15] mercury chloride, [c-28.16] methyl isothiocyanate, [c-28.17] pentachlorophenol, [c-28.18] phosphine, [c -28.19] piperonyl butoxide, [c-28.20] polynactin complexes (polynactins), [c-28.21] sabadilla, [c-28.22] sulcofuron salts (sulcofuron- sodium (sulcofuron-sodium), [c-28.23] tribufos, [c-28.24] aldrin, [c-28.25] amidithion, [c-28.26 ] Amidothioate, [c-28.27] aminocarb, [c-28.28] amiton, [c-28.29] aramite, [c-28.30 ] athidathion, [c-28.31] azothoate, [c-28.32] polysulfide barium (barium polysulfide ), [c-28.33] benclothiaz, [c-28.34] 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone (5- (1,3-benzodioxole-5-yl)-3-hexylcyclohexa-2-enone), [c-28.35] 1,1-bis(4-chlorophenyl)-2-ethoxyethanol (1,1-bis( 4-chlorophenyl)-2-ethoxyethanol), [c-28.36] butonate, [c-28.37] butopyronoxyl, [c-28.38] 2-(2-butoxyethoxy) ethyl Thiocyanate (2-(2-butoxyethoxy)ethyl thiocyanate), [c-28.39] camphechlor, [c-28.40] chlorbenside, [c-28.41] chlordecone, [ c-28.42] chlordimeform, [c-28.43] chlorfenethol, [c-28.44] chlorfenson, [c-28.45] fluazuron , [c-28.46] metaldehyde, [c-28.47] bialaphos, [c-28.48] levamisol hydrochloride, [c-28.49] amidoflumet , [c-28.50] pyrafluprole, [c-28.51] pyriprole, [c-28.52] tralopyril, [c-28.53] flupyrazofos , [c-28.54] diofenolan, [c-28.55] chlorobenzylate, [c-28.56] flufenzine, [c-28.57] benzomate , [c-28.58] flufenerim, [c-28.59] albendazole, [c-28.60] oxybendazole dazole), [c-28.61] fenbendazole, [c-28.62] metam-sodium, [c-28.63] 1,3-dichloropropene (1,3 -dichloropropene), [c-28.64] flometoquin, [c-28.65] cyclaniliprole, [c-28.66] tetraniliprole, [c-28. 67] broflanilide, [c-28.68] dichloromezotiaz, [c-28.69] ethylene dibromide, [c-28.70] acrylonitrile, [ c-28.71] bis (2-chloroethyl) ether (bis (2-chloroethyl) ether), [c-28.72] 1-bromo-2-chloroethane (1-bromo-2-chloroethane), [c- 28.73]3-bromo-1-chloroprop-1-ene, [c-28.74]bromocyclen, [c-28.75]disulfide carbon disulfide, [c-28.76] tetrachloromethane, [c-28.77] nemadectin, [c-28.78] cymiazole [c-28.79] calcium polysulfide, [c-28.80] cytokinin, [c-28.81] 2-(octylthio)ethanol, [c-28.82] potassium oleate, [c -28.83] sodium oleate, [c-28.84] machine oil, [c-28.85] tar oil, [c-28.86] anabasine ( anabasine), [c-28.87] morantel tartrate, [c-28.88] pyrethrum, [c-28.89] rape seed oil), [c-28.90] soybean lecithin, [c-28.91] starch, [c-28.92] hydroxypropylstarch, [c-28.93] fatty acid decanoyloctanoylglycerol, [c-28.94] propylene glycol fatty acid ester, [c-28.95] diatomite, [c-28.96] afoxolaner, [c-28.97] fluazaindolizine, [c-28.98] afidopyropen, [c-28.99] cyhalodiamide, [c-28.100] tioxazafen , [c-28.101] fluhexafon, [c-28.102] fluralaner, [c-28.103] fluxametamide, [c-28.104] tetrachlorantrani tetrachlorantraniliprole, [c-28.105]sarolaner, [c-28.106]lotilaner, [c-28.107]cycloxaprid, [c-28.108]fluene fluensulfone, [c-28.109] TPIC (tripropyl isocyanurate), [c-28.110] DD (1,3-Dichloropropene), [c-28.111] peroxocarbonate, [c-28.112] MB-599 (verbutin), [c-28.113] bis (2,3,3,3-tetrachloropropyl) ether (bis (2,3,3,3-tetrachloropropyl) ether ), [c-28.114] DCIP (bis(2-chloro-1-methylethyl) ether), [c-28.115] ENT-8184 (N-(2-Ethylhexyl)bicyclo[2.2.1] hept-5-ene-2,3-dic ａｒｂｏｘｉｍｉｄｅ）、［ｃ－２８．１１６］Ｂａｙｅｒ ２２４０８（Ｏ,Ｏ－ｄｉｅｔｈｙｌ Ｏ－ｎａｐｈｔｈａｌｉｍｉｄｏ ｐｈｏｓｐｈｏｒｏｔｈｉｏａｔｅ）、［ｃ－２８．１１７］Ｂａｙｅｒ ３２３９４（ｔｒｉｓ（１－ｄｏｄｅｃｙｌ－３－ｍｅｔｈｙｌ－２－ｐｈｅｎｙｌｂｅｎｚｉｍｉｄａｚｏｌｉｕｍ）ｈｅｘａｃｙａｎｏｆｅｒｒａｔｅ） ,
[c-28.118] formula (s34)

A compound represented by (see WO 10/051926),
[c-28.119] formula (s35)

A compound represented by (see WO 13/115391),
[c-28.120] formula (s36)

A compound represented by (see WO 12/029672),
[c-28.121] formula (s37)

A compound represented by (see WO 06/056108),
[c-28.122] formula (s38)

(see International Publication No. 14/053450, International Patent No. 15/144683),
[c-28.123] formula (s39)

(see International Publication No. 14/053450, International Patent No. 15/144683),
[c-28.124] formula (s40)

(see International Publication No. 14/053450, International Patent No. 15/144683),
[c-28.125] formula (s41)

[In the formula, m6 represents an integer of 0 to 2. ] (see WO 10/129497),
[c-28.126] formula (s42)

[In the formula, m7 represents an integer of 0 to 2. ] (see WO 11/152320),
[c-28.127] formula (s43)

[In the formula, m8 represents an integer of 0 to 2. ] (see JP-A-27-160813),
[c-28.128] formula (s44)

[In the formula, A52 represents a hydrogen atom or a fluorine atom. ] (see International Publication No. 11/134964, International Patent No. 14/005982),
[c-28.129] formula (s45)

[In the formula, m9 represents an integer of 0 to 2, and A53 represents a fluorine atom or a chlorine atom. ] (see WO 15/025826),
[c-28.130] formula (s46)

[In the formula, V3 represents a nitrogen atom, a carbon atom, or CF, and V4 and V5 each independently represent a nitrogen atom or a carbon atom. ] (see WO 11/134964, WO 14/005982),
[c-28.131] formula (s47)

[In the formula, A54 represents a hydrogen atom, a methyl group, a methoxy group or an ethoxy group, A55 represents a chlorine atom or a methyl group, and A56 represents a methyl group or an ethyl group. ] (see WO 09/049851),
[c-28.132] formula (s48)

[In the formula, A57 represents a hydrogen atom, a fluorine atom, or a chlorine atom, and A58 is

represents one partial structure selected from the group consisting of ] (see WO 11/067272),
[c-28.133] formula (s49)

[Wherein, A59 represents a hydrogen atom, a fluorine atom, or a chlorine atom, and A60 is

represents a partial structure selected from the group consisting of ] (see WO 10/090344),
[c-28.134] formula (s50)

[Wherein, m10 represents an integer of 0 to 2, A61 represents a trifluoromethyl group, a trifluoromethylthio group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group, A62 represents a hydrogen atom, or represents a trifluoromethyl group, V6 represents a nitrogen atom or a carbon atom, and V7 represents an oxygen atom or an N-methyl group. ] (see WO 14/104407),
[c-28.135] formula (s51)

[Wherein, A63 represents a hydrogen atom or a fluorine atom, an amide group is bonded to the 4th or 5th position, and A64 is

represents a partial structure selected from the group consisting of ] (see International Publication No. 15/038503, International Patent No. 16/144351, International Patent No. 16/144678),
[c-28.136] formula (s52)

[In the formula, A65 represents a hydrogen atom, a C1-C6 alkyl group, or a C1-C6 haloalkyl group, A66 represents a hydrogen atom, a halogen atom, or a C1-C6 alkyl group, and A67 and A68 are , which are each independently a hydrogen atom, a C1 to C6 alkyl group optionally substituted with a cyano group, an alkyl group optionally substituted with a methoxy group, an alkyl group optionally substituted with an ethoxy group, or represents a C3-C8 cycloalkyl group,
A69 represents a hydrogen atom, a cyano group, a C1-C6 haloalkyl group optionally substituted with a cyano group, a C1-C6 alkyl group, or a C3-C8 cycloalkyl group. ] (see International Publication No. 12/143317, International Patent No. 16/016369),
[c-28.137] formula (s53) or formula (s54)

[Wherein, A70 represents a methyl group, an ethyl group, an isopropyl group, a 2,2,2-trifluoroethyl group, or a phenyl group;

A72 represents a partial structure selected from the group consisting of

represents a partial structure selected from the group consisting of V8 represents an oxygen atom, a sulfur atom, —CH ₂ —, or —CH ₂ CH ₂ —. ] (see International Publication No. 14/167084, International Patent No. 16/055431),
[c-28.138] formula (s55)

[Wherein, m11 represents an integer of 0 to 1, A73 represents a chlorine atom, a bromine atom, a methyl group, or a trifluoromethyl group, A74 represents a hydrogen atom, a chlorine atom, a bromine atom, a cyano group, or represents a trifluoromethyl group, A75 represents a hydrogen atom, a chlorine atom or a bromine atom, A76 and A77 each independently represent a C1-C6 alkyl group or a C3-C8 cycloalkyl group, A78 represents a chlorine atom, a bromine atom, a cyano group, a nitro group, a difluoromethyl group, or a trifluoromethyl group. ] (see WO 13/024009),
[c-28.139] formula (s56)

[In the formula, A79, A80, A81 and A82 are each independently a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, or a C3-C8 represents a cycloalkoxy group. ] (see WO 12/027521),
[c-28.140] formula (s57)

[Wherein, m12 represents an integer of 0 to 2, A83 represents a hydrogen atom or a fluorine atom, and A84 represents

represents a partial structure selected from the group consisting of ] (see WO 13/162715),
[c-28.141] acynonapyr,
[c-28.142] formula (s59)

[A90 represents a halogen atom, a C1-C6 alkyl group, or a C1-C6 haloalkyl group, A91 represents a C1-C6 haloalkyl group, A92 and A93 are each independently a hydrogen atom, represents a C1-C6 alkyl group, an acetyl group, a propionoyl group, a methanesulfonylethyl group, a methoxycarbonyl group, or an ethoxycarbonyl group, A94 and A95 each independently represent a hydrogen atom, a C1-C6 alkyl group, or represents a C1-C6 haloalkyl group. ] (see International Publication No. 12/164698) and the like.

The mixing ratio of the compound of the present invention and other pesticides is not particularly limited as long as the effect is exhibited, but usually the weight ratio of the other pesticide to the compound of the present invention is 0.001 to 1000. is a ratio of , preferably a ratio of 0.01 to 100.

The present invention will be illustrated in more detail below by giving Synthesis Examples, Reference Examples and Test Examples, but the present invention is not limited to these.

参考例３で得られた２－（２－クロロ－５－メトキシフェニル）－３－（ジメチルアミノ）－１－（２，４，６－トリフルオロフェニル）－２－プロぺン－１－オン ５００ｍｇを含むトルエン溶液 ２０ｍｌに、メチルウレア ２９８ｍｇとｐ－トルエンスルホン酸・１水和物 １．０ｇを加えて、１３０℃で１５時間撹拌した。室温まで冷却した後に、反応混合物に水と酢酸エチルを加えて分液した。得られた有機層を飽和食塩水で洗浄し、硫酸ナトリウムで乾燥した。減圧下で溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が１８３ｍｇの白色固体として得られた。[Synthesis Example 1]
Synthesis of 2-(2-chloro-5-methoxyphenyl)-1-methyl-6-(2,4,6-trifluorophenyl)pyrimidin-2(1H)-one (Compound No.: 4)

2-(2-chloro-5-methoxyphenyl)-3-(dimethylamino)-1-(2,4,6-trifluorophenyl)-2-propen-1-one obtained in Reference Example 3 298 mg of methylurea and 1.0 g of p-toluenesulfonic acid monohydrate were added to 20 ml of a toluene solution containing 500 mg, and the mixture was stirred at 130° C. for 15 hours. After cooling to room temperature, water and ethyl acetate were added to the reaction mixture to separate the layers. The obtained organic layer was washed with saturated saline and dried with sodium sulfate. After evaporating the solvent under reduced pressure, the obtained residue was purified by silica gel column chromatography. The title compound was obtained as 183 mg of white solid.

合成例１で得られた２－（２－クロロー５－メトキシフェニル）－１－メチル－６－（２，４，６－トリフルオロフェニル）ピリミジン－２（１Ｈ）－オン ６３ｍｇを含むＴＨＦ溶液 ３ｍｌに、２，２，２－トリフルオロエタノール １８μｌと６０％水素化ナトリウム １０ｍｇを加えて、加熱還流下で１４時間撹拌した。室温まで冷却した後に、反応混合物に水と酢酸エチルを加えて分液した。得られた有機層を飽和食塩水で洗浄し、硫酸ナトリウムで乾燥した。 減圧下で溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が４９ｍｇの白色固体として得られた。[Synthesis Example 2]
Synthesis of 5-(2-chloro-5-methoxyphenyl)-6-(2,6-difluoro-4-(2,2,2-trifluoroethoxy)phenyl)-1-methylpyrimidin-2(1H)-one (Compound number: 11)

3 ml of THF solution containing 63 mg of 2-(2-chloro-5-methoxyphenyl)-1-methyl-6-(2,4,6-trifluorophenyl)pyrimidin-2(1H)-one obtained in Synthesis Example 1 18 μl of 2,2,2-trifluoroethanol and 10 mg of 60% sodium hydride were added to the solution, and the mixture was stirred under reflux with heating for 14 hours. After cooling to room temperature, water and ethyl acetate were added to the reaction mixture to separate the layers. The obtained organic layer was washed with saturated saline and dried with sodium sulfate. After evaporating the solvent under reduced pressure, the obtained residue was purified by silica gel column chromatography. 49 mg of the title compound was obtained as a white solid.

２－（２－クロロー５－メトキシフェニル）－１－メチル－６－（２，４，６－トリフルオロフェニル）ピリミジン－２（１Ｈ）－オン ８０ｍｇを含むトルエン溶液 ２ｍｌに、ローソン試薬 １２８ｍｇを加えて、加熱還流下で２時間撹拌した。室温まで冷却した後に、反応混合物に水と酢酸エチルを加えて分液した。得られた有機層を飽和食塩水で洗浄し、硫酸ナトリウムで乾燥した。減圧下で溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が６１ｍｇの黄色固体として得られた。[Synthesis Example 3]
Synthesis of 2-(2-chloro-5-methoxyphenyl)-1-methyl-6-(2,4,6-trifluorophenyl)pyrimidine-2(1H)-thione (Compound No.: 14)

To 2 ml of a toluene solution containing 80 mg of 2-(2-chloro-5-methoxyphenyl)-1-methyl-6-(2,4,6-trifluorophenyl)pyrimidin-2(1H)-one, add 128 mg of Lawesson's reagent. and stirred for 2 hours while heating to reflux. After cooling to room temperature, water and ethyl acetate were added to the reaction mixture to separate the layers. The obtained organic layer was washed with saturated saline and dried with sodium sulfate. After evaporating the solvent under reduced pressure, the obtained residue was purified by silica gel column chromatography. 61 mg of the title compound was obtained as a yellow solid.

製造方法ＡＡを参照にして合成した３－メチル－１－（２，４，６－トリフルオロフェニル）ブタン－１－オン ３．３ｇに、Ｎ，Ｎ－ジメチルホルムアミドジメチルアセタール １０．２ｍｌを加えて、１００℃で１２時間撹拌した。さらに、１２０℃で８時間撹拌した。室温まで冷却した後に、反応混合物に水と酢酸エチルを加えて分液した。得られた有機層を飽和食塩水で洗浄し、硫酸ナトリウムで乾燥した。減圧下で溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物を含む混合物が２．８ｇの黄色油状物質として得られた。これ以上精製することなく、次の反応に使用した。[Synthesis Example 4]
Step 1: Synthesis of 2-((dimethylamino)methylene)-3-methyl-1-methyl-(2,4,6-trifluorophenyl)butan-1-one

10.2 ml of N,N-dimethylformamide dimethylacetal was added to 3.3 g of 3-methyl-1-(2,4,6-trifluorophenyl)butan-1-one synthesized with reference to Production Method AA. and 100° C. for 12 hours. Furthermore, it stirred at 120 degreeC for 8 hours. After cooling to room temperature, water and ethyl acetate were added to the reaction mixture to separate the layers. The obtained organic layer was washed with saturated saline and dried with sodium sulfate. After evaporating the solvent under reduced pressure, the obtained residue was purified by silica gel column chromatography. A mixture containing the title compound was obtained as 2.8 g of a yellow oil. Used for next reaction without further purification.

ステップ１で得られた２－（（ジメチルアミノ）メチレン）－３－メチル－１－メチル－（２，４，６－トリフルオロフェニル）ブタン－１－オン ２．８ｇを含むトルエン溶液 ２０ｍｌに、エチルウレア ２．７ｇとｐ－トルエンスルホン酸・１水和物 ５．３ｇを加えて、加熱還流下で１７時間撹拌した。室温まで冷却した後に、反応混合物に水と酢酸エチルを加えて分液した。得られた有機層を飽和食塩水で洗浄し、硫酸ナトリウムで乾燥した。減圧下で溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が１６５ｍｇの褐色固体として得られた。Step 2: Synthesis of 1-ethyl-5-isopropyl-6-(2,4,6-trifluorophenyl)pyrimidin-2(1H)-one (Compound No.: 18)

In 20 ml of a toluene solution containing 2.8 g of 2-((dimethylamino)methylene)-3-methyl-1-methyl-(2,4,6-trifluorophenyl)butan-1-one obtained in step 1, 2.7 g of ethyl urea and 5.3 g of p-toluenesulfonic acid monohydrate were added, and the mixture was stirred under reflux with heating for 17 hours. After cooling to room temperature, water and ethyl acetate were added to the reaction mixture to separate the layers. The obtained organic layer was washed with saturated saline and dried with sodium sulfate. After evaporating the solvent under reduced pressure, the obtained residue was purified by silica gel column chromatography. 165 mg of the title compound was obtained as a brown solid.

合成例４で得られた１－エチル－５－イソプロピル－６－（２，４，６－トリフルオロフェニル）ピリミジン－２（１Ｈ）－オン ６０ｍｇを含むメタノール溶液 ２ｍｌに、２８％ナトリウムメトキシドのメタノール溶液 １９５μｌを加えて、６０℃で１６時間撹拌した。室温まで冷却した後に、反応混合物に水と酢酸エチルを加えて分液した。得られた有機層を飽和食塩水で洗浄し、硫酸ナトリウムで乾燥した。 減圧下で溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が５７ｍｇの白色固体として得られた。[Synthesis Example 5]
Synthesis of 6-(2,6-difluoro-4-methoxyphenyl)-1-ethyl-5-isopropylpyrimidin-2(1H)-one (Compound No.: 20)

2 ml of a methanol solution containing 60 mg of 1-ethyl-5-isopropyl-6-(2,4,6-trifluorophenyl)pyrimidin-2(1H)-one obtained in Synthesis Example 4 was added with 28% sodium methoxide. 195 μl of methanol solution was added and stirred at 60° C. for 16 hours. After cooling to room temperature, water and ethyl acetate were added to the reaction mixture to separate the layers. The obtained organic layer was washed with saturated saline and dried with sodium sulfate. After evaporating the solvent under reduced pressure, the obtained residue was purified by silica gel column chromatography. 57 mg of the title compound was obtained as a white solid.

１－エチル－５－イソプロピル－６－（２，４，６－トリフルオロフェニル）ピリミジン－２（１Ｈ）－オン １００ｍｇを含むトルエン溶液 ３ｍｌに、ローソン試薬 １７４ｍｇを加えて、加熱還流下で２時間撹拌した。室温まで冷却した後に、反応混合物に水と酢酸エチルを加えて分液した。得られた有機層を飽和食塩水で洗浄し、硫酸ナトリウムで乾燥した。 減圧下で溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が９４ｍｇの黄色固体として得られた。[Synthesis Example 6]
Synthesis of 1-ethyl-5-isopropyl-6-(2,4,6-trifluorophenyl)pyrimidine-2(1H)-thione (Compound No.: 21)

174 mg of Lawesson's reagent was added to 3 ml of a toluene solution containing 100 mg of 1-ethyl-5-isopropyl-6-(2,4,6-trifluorophenyl)pyrimidin-2(1H)-one, and the mixture was heated under reflux for 2 hours. Stirred. After cooling to room temperature, water and ethyl acetate were added to the reaction mixture to separate the layers. The obtained organic layer was washed with saturated saline and dried with sodium sulfate. After evaporating the solvent under reduced pressure, the obtained residue was purified by silica gel column chromatography. 94 mg of the title compound was obtained as a yellow solid.

合成例４で得られた１－エチル－５－イソプロピル－６－（２，４，６－トリフルオロフェニル）ピリミジン－２（１Ｈ）－チオン ４６ｍｇを含むメタノール溶液 ３ｍｌに、２８％ナトリウムメトキシドのメタノール溶液 １４２μｌを加えて、６０℃で４時間撹拌した。室温まで冷却した後に、反応混合物に水と酢酸エチルを加えて分液した。得られた有機層を飽和食塩水で洗浄し、硫酸ナトリウムで乾燥した。 減圧下で溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が４３ｍｇの黄色固体として得られた。[Synthesis Example 7]
Synthesis of 1-ethyl-5-isopropyl-6-(2,4,6-trifluorophenyl)pyrimidine-2(1H)-thione (Compound No.: 22)

To 3 ml of a methanol solution containing 46 mg of 1-ethyl-5-isopropyl-6-(2,4,6-trifluorophenyl)pyrimidine-2(1H)-thione obtained in Synthesis Example 4, 28% sodium methoxide was added. 142 μl of methanol solution was added and stirred at 60° C. for 4 hours. After cooling to room temperature, water and ethyl acetate were added to the reaction mixture to separate the layers. The obtained organic layer was washed with saturated saline and dried with sodium sulfate. After evaporating the solvent under reduced pressure, the obtained residue was purified by silica gel column chromatography. 43 mg of the title compound was obtained as a yellow solid.

参考例６を参照にして得られた５，６－ビス（２－フルオロフェニル）ピラジン－２（１Ｈ）－オン ５００ｍｇを含むＤＭＦ溶液 １０ｍｌに、ヨウ化エチル ４４２μｌと炭酸カリウム７２９ｍｇを加えて、４０℃で５時間撹拌した。室温まで冷却した後に、反応混合物に水と酢酸エチルを加えて分液した。得られた有機層を飽和食塩水で洗浄し、硫酸ナトリウムで乾燥した。 減圧下で溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が１３４ｍｇの透明油状物質として得られた。[Synthesis Example 8]
Synthesis of 1-ethyl-5,6-bis(2-fluorophenyl)pyrazin-2(1H)-one (compound number: 7)

To 10 ml of a DMF solution containing 500 mg of 5,6-bis(2-fluorophenyl)pyrazin-2(1H)-one obtained with reference to Reference Example 6, 442 μl of ethyl iodide and 729 mg of potassium carbonate were added to obtain 40 C. for 5 hours. After cooling to room temperature, water and ethyl acetate were added to the reaction mixture to separate the layers. The obtained organic layer was washed with saturated saline and dried with sodium sulfate. After evaporating the solvent under reduced pressure, the obtained residue was purified by silica gel column chromatography. 134 mg of the title compound was obtained as a clear oil.

合成例８で得られた１－エチル－５，６－ビス（２－フルオロフェニル）ピラジン－２（１Ｈ）－オン １３０ｍｇを含むＤＭＦ溶液 ５ｍｌに、Ｎ－クロロスクシンイミド １１１ｍｇを加えて、７０℃で３時間撹拌した。室温まで冷却した後に、反応混合物に水と酢酸エチルを加えて分液した。得られた有機層を飽和食塩水で洗浄し、硫酸ナトリウムで乾燥した。 減圧下で溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が１２５ｍｇの白色固体として得られた。[Synthesis Example 9]
Synthesis of 3-chloro-1-ethyl-5,6-bis(2-fluorophenyl)pyrazin-2(1H)-one (compound number: 10)

111 mg of N-chlorosuccinimide was added to 5 ml of a DMF solution containing 130 mg of 1-ethyl-5,6-bis(2-fluorophenyl)pyrazin-2(1H)-one obtained in Synthesis Example 8, and the mixture was stirred at 70°C. Stirred for 3 hours. After cooling to room temperature, water and ethyl acetate were added to the reaction mixture to separate the layers. The obtained organic layer was washed with saturated saline and dried with sodium sulfate. After evaporating the solvent under reduced pressure, the obtained residue was purified by silica gel column chromatography. 125 mg of the title compound was obtained as a white solid.

水酸化ナトリウム ４．０ｇを溶解した水溶液 ６００ｍｌに、 Ｎ－（３－メトキシベンジリデン）－４－メチルベンゼンスルホニルヒドラジド ３０．４ｇを加えて、均一になるまで室温下で撹拌した。続いて、２，４，６－トリフルオロベンズアルデヒド ８．０ｇを加えて、８０℃で１時間撹拌した。室温まで冷却した後に、反応混合物に酢酸エチルを加えて分液した。得られた有機層を飽和塩化アンモニウム水溶液と飽和食塩水で順次洗浄し、硫酸ナトリウムで乾燥した。減圧下で溶媒留去を行い、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が６．４ｇの無色油状物質として得られた。[Reference example 1]
Synthesis of 2-(3-methoxyphenyl)-1-(2,4,6-trifluorophenyl)ethanone

30.4 g of N-(3-methoxybenzylidene)-4-methylbenzenesulfonylhydrazide was added to 600 ml of an aqueous solution in which 4.0 g of sodium hydroxide was dissolved, and the mixture was stirred at room temperature until uniform. Subsequently, 8.0 g of 2,4,6-trifluorobenzaldehyde was added and stirred at 80° C. for 1 hour. After cooling to room temperature, ethyl acetate was added to the reaction mixture to separate the layers. The obtained organic layer was washed successively with saturated aqueous ammonium chloride solution and saturated brine, and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography. 6.4 g of the title compound were obtained as a colorless oil.

参考例１で得られた２－（３－メトキシフェニル）－１－（２，４，６－トリフルオロフェニル）エタノン ６．４ｇを含むＤＭＦ溶液６０ｍｌに、Ｎ－クロロスクシンイミド ３．４ｇを加えて、７５℃で１．５時間撹拌した。室温まで冷却した後に、反応混合物に水と酢酸エチルを加えて分液した。得られた有機層を飽和食塩水で洗浄し、硫酸ナトリウムで乾燥した。 減圧下で溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が５．１ｇの白色固体として得られた。 ¹ H-NMR (CDCl ₃ ) δ: 7.21 (1H, m), 6.80-6.78 (2H, m), 6.75 (1H, m), 6.68-6.65 (2H , m), 4.10 (2H, s), 3.77 (3H, s).
[Reference example 2]
Synthesis of 2-(2-chloro-5-methoxyphenyl)-1-(2,4,6-trifluorophenyl)ethanone

3.4 g of N-chlorosuccinimide was added to 60 ml of a DMF solution containing 6.4 g of 2-(3-methoxyphenyl)-1-(2,4,6-trifluorophenyl)ethanone obtained in Reference Example 1. at 75° C. for 1.5 hours. After cooling to room temperature, water and ethyl acetate were added to the reaction mixture to separate the layers. The obtained organic layer was washed with saturated saline and dried with sodium sulfate. After evaporating the solvent under reduced pressure, the obtained residue was purified by silica gel column chromatography. The title compound was obtained as 5.1 g of white solid.

参考例２で得られた２－（２－クロロ－５－メトキシフェニル）－１－（２，４，６－トリフルオロフェニル）エタノン １．５ｇに、Ｎ，Ｎ－ジメチルホルムアミドジメチルアセタール ３．２ｍｌを加えて、５０℃で３時間撹拌した。室温まで冷却した後に、反応混合物に水と酢酸エチルを加えて分液した。得られた有機層を飽和食塩水で洗浄し、硫酸ナトリウムで乾燥した。減圧下で溶媒留去した後に、得られた残渣をジイソプロピルエーテルとヘキサンで洗浄した。表題の化合物が１．６ｇの白色固体として得られた。 ¹ H-NMR (CDCl ₃ ) δ: 7.27 (1H, d, J = 8.5 Hz), 6.81 (1H, d, J = 3.1 Hz), 6.75 (1H, dd, J = 8.5, 3.1 Hz), 6.73-6.70 (2H, m), 4.24 (2H, s), 3.78 (3H, s).
[Reference example 3]
Synthesis of 2-(2-chloro-5-methoxyphenyl)-3-(dimethylamino)-1-(2,4,6-trifluorophenyl)-2-propen-1-one

To 1.5 g of 2-(2-chloro-5-methoxyphenyl)-1-(2,4,6-trifluorophenyl)ethanone obtained in Reference Example 2, 3.2 ml of N,N-dimethylformamide dimethylacetal was added and stirred at 50° C. for 3 hours. After cooling to room temperature, water and ethyl acetate were added to the reaction mixture to separate the layers. The obtained organic layer was washed with saturated saline and dried with sodium sulfate. After evaporating the solvent under reduced pressure, the resulting residue was washed with diisopropyl ether and hexane. The title compound was obtained as 1.6 g of white solid.

２－（２－フルオロフェニル）酢酸 ５．０ｇを含むＴＨＦ溶液 １５０ｍｌを－７８℃に冷却した後に、１．９ｍｏｌ／ＬのヘキサメチルジシラザンナトリウムのＴＨＦ溶液 ５４．６ｍｌを－６５℃以下で滴下して、－７８℃で１０分間撹拌した。これに２－フルオロ安息香酸メチル ５．０ｇを含むＴＨＦ溶液 ５ｍｌを－７８℃で滴下した後に、室温まで昇温して３０分間撹拌した。反応混合物に飽和塩化アンモニウム水溶液を加えて撹拌した後に、酢酸エチルを加えて分液した。得られた有機層を飽和食塩水で洗浄して、硫酸ナトリウムで乾燥した。減圧下にて溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製することにより、表題の化合物を７．５ｇの白色固体として得た。 ¹ H-NMR (CDCl ₃ ) δ: 8.02 (1H, br s), 7.47-7.16 (1H, m), 7.05-6.73 (2H, m), 6.45- 6.43 (1H, m), 3.80-3.69 (3H, m), 3.22-2.54 (6H, m).
[Reference Example 4]
Synthesis of 1,2-bis(2-fluorophenyl)ethan-1-one

After cooling 150 ml of a THF solution containing 5.0 g of 2-(2-fluorophenyl)acetic acid to −78° C., 54.6 ml of a 1.9 mol/L THF solution of sodium hexamethyldisilazane was added dropwise at −65° C. or lower. and stirred at -78°C for 10 minutes. After 5 ml of a THF solution containing 5.0 g of methyl 2-fluorobenzoate was added dropwise thereto at -78°C, the mixture was warmed to room temperature and stirred for 30 minutes. After adding a saturated aqueous ammonium chloride solution to the reaction mixture and stirring, ethyl acetate was added to separate the layers. The obtained organic layer was washed with saturated saline and dried with sodium sulfate. After evaporating the solvent under reduced pressure, the obtained residue was purified by silica gel column chromatography to obtain 7.5 g of the title compound as a white solid.

参考例４で得られた１，２－ビス（２－フルオロフェニル）エタン－１－オン １．０ｇを含むＤＭＳＯ溶液 １５ｍｌに、酸化銅（II）３４３ｍｇとヨウ素 １．２ｇを加えて、１００℃で５時間撹拌した。室温まで冷却した後に、反応混合物に、１％チオ硫酸ナトリウム水溶液を加えて撹拌した後に、酢酸エチルを加えて分液した。得られた有機層を飽和食塩水で洗浄して、硫酸ナトリウムで乾燥した。減圧下にて溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製することにより、表題の化合物を５８０ｍｇの白色固体として得た。 ¹ H-NMR (CDCl ₃ ) δ: 7.90 (1H, td, J = 7.6, 1.9 Hz), 7.57-7.51 (1H, m), 7.30-7.05 (6H, m), 4.33 (2H, d, J = 2.2 Hz).
[Reference Example 5]
Synthesis of 2-bis(2-fluorophenyl)ethane-1,2-dione

To 15 ml of DMSO solution containing 1.0 g of 1,2-bis(2-fluorophenyl)ethan-1-one obtained in Reference Example 4, 343 mg of copper (II) oxide and 1.2 g of iodine were added, and the mixture was heated to 100°C. for 5 hours. After cooling to room temperature, a 1% aqueous sodium thiosulfate solution was added to the reaction mixture and the mixture was stirred, and then ethyl acetate was added to separate the layers. The obtained organic layer was washed with saturated saline and dried with sodium sulfate. After evaporating the solvent under reduced pressure, the obtained residue was purified by silica gel column chromatography to obtain 580 mg of the title compound as a white solid.

参考例５で得られた１，２－ビス（２－フルオロフェニル）エタン－１，２－ジオン ５８０ｍｇ、グリシンアミド塩酸塩 ２６０ｍｇ含むメタノール溶液 ５ｍｌに、１２Ｎの水酸化ナトリウム水溶液を室温下で加えて、加熱還流下で５時間撹拌した。室温まで冷却した後に、反応混合物に、１Ｎ塩酸水溶液を加えて中和した後に、酢酸エチルを加えて分液した。得られた有機層を飽和食塩水で洗浄して、硫酸ナトリウムで乾燥した。減圧下にて溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製することにより、表題の化合物を３７５ｍｇの黄色固体として得た。 ¹ H-NMR (CDCl ₃ ) δ: 8.09-8.07 (2H, m), 7.69-7.64 (2H, m), 7.36 (2H, td, J = 7.6, 1.1 Hz), 7.15 (2H, ddd, J = 10.5, 8.5, 1.1 Hz).
[Reference Example 6]
Synthesis of 5,6-bis(2-fluorophenyl)pyrazin-2(1H)-one

To 5 ml of a methanol solution containing 580 mg of 1,2-bis(2-fluorophenyl)ethane-1,2-dione obtained in Reference Example 5 and 260 mg of glycinamide hydrochloride, 12N aqueous sodium hydroxide solution was added at room temperature. , and stirred under reflux for 5 hours. After cooling to room temperature, the reaction mixture was neutralized by adding a 1N hydrochloric acid aqueous solution, and then ethyl acetate was added to separate the layers. The obtained organic layer was washed with saturated saline and dried with sodium sulfate. After evaporating the solvent under reduced pressure, the obtained residue was purified by silica gel column chromatography to obtain 375 mg of the title compound as a yellow solid.

¹ H-NMR (CDCl ₃ ) δ: 8.20 (1H, s), 7.41-7.40 (1H, m), 7.35-7.29 (3H, m), 7.18-7 .12 (3H, m), 7.07-7.02 (1H, m).

Table 4 shows compounds synthesized according to the above examples, but the present invention is not limited to these.
In Table 4, Ph represents a phenyl group and 3-Py represents a pyridin-3-yl group. means a phenyl group having fluorine atoms bonded to the 4- and 6-positions, and the description “2-Cl-3-Py” means pyridine-3 having a chlorine atom bonded to the 2-position -yl group, and other descriptions are the same. In R6 and R7, the description of "-" indicates that they do not have a substituent.

In Table 4, structure A shows the following.

In Table 4, structure B shows the following.

In Table 4, structure C shows the following.

In Table 4, structure D shows the following.

Next, for the compounds listed in Table 4, Table 5 shows their ¹ H-NMR data.

Next, the effectiveness of the compounds of the present invention against plant diseases will be specifically shown, but the present invention is not limited to these examples.

[Test Example A] Rice blast Seeds of a test plant (rice cultivar: Kofu) were sown and cultivated until the second leaf developed. In the test, the compound of the present invention was dissolved in a dimethylsulfoxide-methanol mixed solution (volume ratio: 9/1) and diluted with well water to a concentration of 250 ppm to obtain a chemical solution. The resulting chemical solution was sprayed on the test plants (2.5 ml/pot). After the chemical solution had dried, the plants were spray-inoculated with a conidia suspension of 1 to 2×10 ⁵ conidia/ml of Magnaporthe grisea. After inoculation, the plants were left in a moist room at a room temperature of 20 to 23°C for about 24 hours to promote disease development. 6 to 10 days after inoculation, the degree of disease development was investigated to evaluate the effect of the drug solution.

[Test Example B] Gray mold of tomato Seeds of a test plant (tomato variety: Dai Fukuju) were sown and cultivated until 3 to 5 true leaves developed. In the test, the compound of the present invention was dissolved in a dimethylsulfoxide-methanol mixed solution (volume ratio: 9/1) and diluted with well water to a concentration of 250 ppm to obtain a chemical solution. The resulting chemical solution was sprayed on the test plants (2.5 ml/pot). After the chemical solution had dried, the plants were spray-inoculated with a conidia suspension of 4-8×10 ⁵ cells/ml of Botrytis cinerea. After inoculation, the plants were left in a moist room at a room temperature of 20 to 23°C for about 48 hours to promote disease development. 2 to 3 days after inoculation, the degree of disease development was investigated to evaluate the effect of the drug solution.

[Test Example C] Cabbage black soot disease Seeds of a test plant (cabbage variety: Shikimi) were sown and cultivated until cotyledons developed. In the test, the compound of the present invention was dissolved in a dimethylsulfoxide-methanol mixed solution (volume ratio: 9/1) and diluted with well water to a concentration of 250 ppm to obtain a chemical solution. The resulting chemical solution was sprayed on the test plants (2.5 ml/pot). After the chemical solution had dried, the plants were spray-inoculated with a conidia suspension of 4-8×10 ⁵ cells/ml of Alternaia brassicicola. After inoculation, the plants were left in a moist room at a room temperature of 20 to 23°C for about 48 hours to promote disease development. 2 to 3 days after inoculation, the degree of disease development was investigated to evaluate the effect of the drug solution.

[Test Example D] Barley Powdery Mildew Seeds of a test plant (barley variety: Akashinriki) were sown and cultivated until the first leaves developed. In the test, the compound of the present invention was dissolved in a dimethylsulfoxide-methanol mixed solution (volume ratio: 9/1) and diluted with well water to a concentration of 250 ppm to obtain a chemical solution. The resulting chemical solution was sprayed on the test plants (2.5 ml/pot). After the chemical solution had dried, the plants were inoculated with conidia of barley powdery mildew (Blumeria graminis f.sp.hordei) by knocking them down. After 6 to 10 days after inoculation, the degree of disease onset was investigated to evaluate the effect.

[Test Example E] Wheat leaf rust Seeds of a test plant (wheat variety: Norin No. 61) were sown and cultivated until the first leaves developed. In the test, the compound of the present invention was dissolved in a dimethylsulfoxide-methanol mixed solution (volume ratio: 9/1) and diluted with well water to a concentration of 250 ppm to obtain a chemical solution. The resulting chemical solution was sprayed on the test plants (2.5 ml/pot). After the chemical solution had dried, the plants were spray-inoculated with a urediniospore suspension of 1 to 2×10 ⁵ cells/ml of Puccinia recondita. After inoculation, the plants were left in a moist room at a room temperature of 20 to 23°C for about 24 hours to promote disease development. 7 to 10 days after inoculation, the degree of disease development was investigated to evaluate the effect of the drug solution.

[Test Example F] Late blight of tomato Seeds of a test plant (tomato variety: Dai Fukuju) were sown and cultivated until 3 to 5 true leaves developed. In the test, the compound of the present invention was dissolved in a dimethylsulfoxide-methanol mixed solution (volume ratio: 9/1) and diluted with well water to a concentration of 250 ppm to obtain a chemical solution. The resulting chemical solution was sprayed on the test plants (2.5 ml/pot). After the chemical solution had dried, the plants were spray inoculated with a zoosporangial suspension of Phytophthora infestans at 4-8×10 ³ cells/ml. After inoculation, the plants were left in a moist room at a room temperature of 20°C for about 24 hours to promote disease development. 5 to 10 days after inoculation, the degree of disease development was investigated to evaluate the effect of the drug solution.

[Test Example G] Downy mildew of a test plant (grape variety: Neo Muscat) was sown and cultivated until 3 to 4 true leaves developed. In the test, the compound of the present invention was dissolved in a dimethylsulfoxide-methanol mixed solution (volume ratio: 9/1) and diluted with well water to a concentration of 250 ppm to obtain a chemical solution. The resulting chemical solution was sprayed on the test plants (2.5 ml/pot). After the chemical solution had dried, the plants were inoculated by spraying a zoosporangial suspension of Plasmopara viticola at 1-2×10 ⁴ cells/ml. After inoculation, the plants were left in a moist room at a room temperature of 20°C for about 24 hours to promote disease development. 7 to 10 days after inoculation, the degree of disease development was investigated to evaluate the effect of the drug solution.

[Test Example H] Cucumber anthracnose Seeds of a test plant (cucumber variety: Sagamihanjiro) were sown and cultivated until one true leaf developed. In the test, the compound of the present invention was dissolved in a dimethylsulfoxide-methanol mixed solution (volume ratio: 9/1) and diluted with well water to a concentration of 250 ppm to obtain a chemical solution. The resulting chemical solution was sprayed on the test plants (2.5 ml/pot). After the chemical solution had dried, the plants were spray-inoculated with a conidia suspension of 2-4×10 ⁵ cells/ml of Colletotrichum orbiculare. After inoculation, the plants were left in a moist room at a room temperature of 20 to 23°C for about 24 hours to promote disease development. 6 to 10 days after inoculation, the degree of disease development was investigated to evaluate the effect of the drug solution.

With regard to the degree of disease onset in the above test examples, the degree of disease onset in non-diseased plants was set to 0, and the degree of disease onset in plants not treated with chemicals was set to 3, and the degree of disease onset was evaluated in increments of 0.05. In addition, the preventive value was calculated from the degree of disease according to the following formula.

<Control value>
Control value = 100 {1-(n/3)}
Table 6 shows a summary of the test results for n=the degree of disease onset in each drug-treated plot. In the table, H indicates that the control value is greater than 50%, and L indicates that the control value is 50% or less. Moreover, nt represents that the test was not performed.

The nitrogen-containing heterocyclic compound or salt thereof of the present invention is a novel compound and can control plant diseases, so it is useful as an agricultural chemical, such as an agricultural and horticultural pest control agent, especially an agricultural and horticultural fungicide. There is

The disclosure of Japanese Patent Application No. 2017-112817 (filing date: June 7, 2017) is incorporated herein by reference in its entirety.
All publications, patent applications and technical standards mentioned herein are to the same extent as if each individual publication, patent application and technical standard were specifically and individually noted to be incorporated by reference. incorporated herein by reference.

Claims (8)

formula (1)

[In the formula, R1 is
hydroxyl group,
cyano group,
a C1-C6 alkyl group optionally substituted with a substituent A,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with a substituent A,
a C2-C6 alkenyl group optionally substituted with a substituent A,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted with a substituent A,
a C2-C6 haloalkynyl group,
a C1-C6 alkoxy group optionally substituted with a substituent A,
a C1-C6 haloalkoxy group,
a C3-C8 cycloalkoxy group optionally substituted with a substituent A;
a C2-C6 alkenyloxy group optionally substituted with a substituent A,
a C2-C6 haloalkenyloxy group,
a C3-C6 alkynyloxy group optionally substituted with a substituent A,
a C3-C6 haloalkynyloxy group,
or RaRbN- (wherein Ra and Rb are each independently a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, or a C3-C8 Alternatively, Ra and Rb together with the attached nitrogen atom form an aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl, homopiperidinyl, or azocanyl group). represent;
R2 is
cyano group,
a C1-C6 alkyl group optionally substituted with a substituent A,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with a substituent A,
a C2-C6 alkenyl group optionally substituted with a substituent A,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted with a substituent A,
a C2-C6 haloalkynyl group,
a C1-C6 alkoxy group optionally substituted with a substituent A,
a C1-C6 haloalkoxy group,
a C3-C8 cycloalkoxy group optionally substituted with a substituent A,
RaRbN- (where Ra and Rb are as defined above),
Rx1C(=O)-(wherein Rx1 is a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or RaRbN- (wherein Ra and Rb are as defined above.),
phenyl group,
a 5- to 6-membered heterocyclic group,
or represents an 8- to 10-membered heterocyclic group,
the phenyl group is optionally substituted with 0 to 5 R3 (provided that when there are two or more substituted R3, each R3 represents an independent substituent);
The 5- to 6-membered heterocyclic group or the 8- to 10-membered heterocyclic group is optionally substituted with 0 to 6 R3 (provided that when there are 2 or more R3s, each R3 is an independent substituent. show.);
R3 is
hydroxyl group,
cyano group,
nitro group,
halogen atom,
a C1 to C6 alkyl group optionally substituted with a substituent C,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with a substituent C,
a C2-C6 alkenyl group optionally substituted with a substituent C,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted with a substituent C,
a C2-C6 haloalkynyl group,
a C1-C6 alkoxy group optionally substituted with a substituent C,
a C1-C6 haloalkoxy group,
a C3-C8 cycloalkoxy group optionally substituted with a substituent C,
a C2-C6 alkenyloxy group optionally substituted with a substituent C,
a C2-C6 haloalkenyloxy group,
a C3-C6 alkynyloxy group optionally substituted with a substituent C,
a C3-C6 haloalkynyloxy group,
an aryl group optionally substituted with a substituent D,
a heteroaryl group optionally substituted with a substituent D,
an aryloxy group optionally substituted with a substituent D,
a heteroaryloxy group optionally substituted with a substituent D,
an aralkyloxy group optionally substituted with a substituent D,
RaRbN- (wherein Ra and Rb are as defined above),
Rc-L- (wherein Rc represents a C1-C6 alkyl group or a C1 _- C6 haloalkyl group, and L represents S, SO, or SO2),
Rx1C (=O) - (where Rx1 is as defined above),
Rx1C(=O)O- (wherein Rx1 has the same definition as above),
Rx2C(=O)N(Rx3)- (here, Rx2 is a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or RaRbN- (wherein Ra and Rb are as defined above), and Rx3 is represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group),
Rx4Rx5C=NO- (here, Rx4 and Rx5 are each independently a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3- represents a C8 cycloalkyl group, a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group, or RaRbN— (wherein Ra and Rb are as defined above); ),
or represents a 3- to 6-membered ring group containing 1 to 2 oxygen atoms;
Y is
a phenyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, a tetrazinyl group, a thienyl group, a thiazolyl group, an isothiazolyl group, or a thiadiazolyl group;
the phenyl group is substituted with R4 at the ortho position and further optionally substituted with 0 to 4 R5 (provided that when there are two or more substituted R5, each R5 represents an independent substituent);
The pyridyl group, the pyridazinyl group, the pyrimidinyl group, the pyrazinyl group, the triazinyl group, or the tetrazinyl group is substituted with R4 at the ortho position, and optionally with 0 to 3 substituents with R5 (provided that 2 or more substituents are substituted). When R5 is present, each R5 represents an independent substituent.),
In the thienyl group, the thiazolyl group, the isothiazolyl group, or the thiadiazolyl group, R4 is substituted at the ortho position, and R5 is optionally substituted with 0 to 2 (provided that when there are two or more substituted R5, each R5 is represents an independent substituent.),
R4 is
hydroxyl group,
cyano group,
nitro group,
halogen atom,
a C1 to C6 alkyl group optionally substituted with a substituent C,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with a substituent C,
a C2-C6 alkenyl group optionally substituted with a substituent C,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted with a substituent C,
a C2-C6 haloalkynyl group,
a C1-C6 alkoxy group optionally substituted with a substituent C,
a C1-C6 haloalkoxy group,
a C3-C8 cycloalkoxy group optionally substituted with a substituent C,
a C2-C6 alkenyloxy group optionally substituted with a substituent C,
a C2-C6 haloalkenyloxy group,
a C3-C6 alkynyloxy group optionally substituted with a substituent C,
a C3-C6 haloalkynyloxy group,
an aryl group optionally substituted with a substituent D,
a heteroaryl group optionally substituted with a substituent D,
an aralkyloxy group optionally substituted with a substituent D,
RaRbN- (wherein Ra and Rb are as defined above),
Rc-L- (wherein Rc and L are as defined above),
Rx1C (=O) - (where Rx1 is as defined above),
Rx1C(=O)O- (wherein Rx1 has the same definition as above),
Rx2C(=O)N(Rx3)- (here, Rx2 is a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or RaRbN- (wherein Ra and Rb are as defined above), and Rx3 is represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group),
Rx4Rx5C=NO- (here, Rx4 and Rx5 are each independently a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3- represents a C8 cycloalkyl group, a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group, or RaRbN- (wherein Ra and Rb are as defined above); ),
or represents a 3- to 6-membered ring group containing 1 to 2 oxygen atoms,
R5 has the same definition as R4 described above;
Z1 represents C—R6 or a nitrogen atom;
Z2 represents C—R7 or a nitrogen atom;
at least one of said Z1 and said Z2 represents a nitrogen atom;
R6 is
hydrogen atom,
halogen atom,
a C1-C6 alkyl group C1-C6 haloalkyl group optionally substituted with a substituent A;
a C3-C8 cycloalkyl group optionally substituted with a substituent A,
a C2-C6 alkenyl group optionally substituted with a substituent A,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted with a substituent A,
a C2-C6 haloalkynyl group,
a C1-C6 alkoxy group optionally substituted with a substituent A,
a C1-C6 haloalkoxy group,
or Rc-L- (wherein Rc and L are as defined above);
R7 is
hydrogen atom,
halogen atom,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with a substituent A,
a C2-C6 alkenyl group optionally substituted with a substituent A,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted with a substituent A,
a C2-C6 haloalkynyl group,
a C1-C6 alkoxy group optionally substituted with a substituent A,
a C1-C6 haloalkoxy group,
Rc-L- (wherein Rc and L are as defined above),
or Rx1C (=O) - (wherein Rx1 is as defined above);
X represents an oxygen atom or a sulfur atom;
And the substituent A is
hydroxyl group,
cyano group,
a C3-C8 cycloalkyl group,
a C1-C6 alkoxy group,
a C1-C6 haloalkoxy group,
a C3-C8 cycloalkoxy group,
RaRbN- (where Ra and Rb are as defined above),
and Rc-L- (wherein Rc and L are as defined above); at least one selected from the group;
Substituent B is
cyano group,
a C1-C6 alkoxy group,
a C1-C6 haloalkoxy group,
and at least one selected from the group consisting of C3-C8 cycloalkoxy groups;
Substituent C is
hydroxyl group,
cyano group,
a C3-C8 cycloalkyl group,
a C1-C6 alkoxy group,
a C1-C6 haloalkoxy group,
a C3-C8 cycloalkoxy group,
a C2-C6 alkoxyalkoxy group,
RaRbN- (where Ra and Rb are as defined above),
Rc-L- (wherein Rc and L are as defined above),
Rx1C (=O) - (where Rx1 is as defined above),
Rx6Rx7Rx8Si- (wherein Rx6, Rx7 and Rx8 each independently represent a C1-C6 alkyl group),
and at least one selected from the group consisting of a 3- to 6-membered ring group containing 1 to 2 oxygen atoms;
Substituent D is
hydroxyl group,
cyano group,
nitro group,
halogen atom,
a C1-C6 alkyl group optionally substituted by a substituent B,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group,
a C1-C6 alkoxy group,
a C1-C6 haloalkoxy group,
and at least one selected from the group consisting of C3-C8 cycloalkoxy groups. ] A nitrogen-containing heterocyclic compound or a salt thereof. R2 is
cyano group,
a C1-C6 alkyl group optionally substituted with a substituent A,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with a substituent A,
a C2-C6 alkenyl group optionally substituted with a substituent A,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted with a substituent A,
a C2-C6 haloalkynyl group,
a C1-C6 alkoxy group optionally substituted with a substituent A,
a C1-C6 haloalkoxy group,
a C3-C8 cycloalkoxy group optionally substituted with a substituent A;
RaRbN- (wherein Ra and Rb are each independently a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, or a C3-C8 cyclo an alkyl group, or Ra and Rb together with the attached nitrogen atom form an aziridinyl group, azetidinyl group, pyrrolidinyl group, piperidinyl group, homopiperidinyl group, or azocanyl group),
Rx1C(=O)-(wherein Rx1 is a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or RaRbN- (wherein Ra and Rb are as defined above.),
phenyl group, pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, tetrazinyl group, thienyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, thiatriazolyl group, pyrrolyl group, pyrazolyl group, imidazolyl group, triazolyl group, tetrazolyl group , pentazolyl group, furyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, indolyl group, isoindolyl group, indazolyl group, benzimidazolyl group, benzotriazolyl group, benzofuryl group, isobenzofuryl group, benzoxazolyl group, benzothienyl group, benzothiazolyl group, benzoisothiazolyl group, benzothiadiazolyl group, indolizinyl group, imidazopyridyl group, pyrazolopyridyl group, triazolopyridyl group, pyrrolopyrimidinyl group, imidazopyrimidinyl group, pyrazolopyrimidinyl group, triazolopyrimidinyl group a pyrrolopyrazinyl group, an imidazopyrazinyl group, a pyrazolopyrazinyl group, a triazolopyrazinyl group, a quinolyl group, an isoquinolyl group, a cinolyl group, a phthalazinyl group, a quinoxalinyl group, a quinazolinyl group, or a napthyridinyl group;
the phenyl group is optionally substituted with 0 to 5 R3 (provided that when there are two or more substituted R3, each R3 represents an independent substituent);
The pyridyl group, the pyridazinyl group, the pyrimidinyl group, the pyrazinyl group, the triazinyl group, or the tetrazinyl group is optionally substituted with 0 to 4 R3s (provided that when there are two or more R3s, each R3 is independently represents a substituent that has
The thienyl group, the thiazolyl group, the isothiazolyl group, the thiadiazolyl group, or the thiatriazolyl group is optionally substituted by 0 to 3 R3 (provided that when there are two or more substituted R3, each R3 is an independent substituent. show.),
The pyrrolyl group, the pyrazolyl group, the imidazolyl group, the triazolyl group, the tetrazolyl group, or the pentazolyl group is optionally substituted with 0 to 4 R3 (provided that when there are two or more R3 substituted, each R3 is independently represents a substituent that has
the furyl group, the oxazolyl group, the isoxazolyl group, or the oxadiazolyl group is optionally substituted with 0 to 3 R3 (provided that when there are two or more substituted R3, each R3 represents an independent substituent);
The indolyl group, the isoindolyl group, the indazolyl group, the benzimidazolyl group, or the benzotriazolyl group is optionally substituted with 0 to 6 R3s (provided that when there are two or more R3s, each R3 is independently represents a substituent.),
The benzofuryl group, the isobenzofuryl group, or the benzoxazolyl group is optionally substituted with 0 to 5 R3 (provided that when there are two or more R3 substituted, each R3 represents an independent substituent). ,
The benzothienyl group, the benzothiazolyl group, the benzoisothiazolyl group, or the benzothiadiazolyl group is optionally substituted with 0 to 5 R3 (provided that when there are two or more substituted R3, each R3 is independently represents a substituent.),
The indolizinyl group, the imidazopyridyl group, the pyrazolopyridyl group, or the triazolopyridyl group is optionally substituted with 0 to 6 R3s (provided that when there are two or more R3s, each R3 is an independent substituent represents ),
The pyrrolopyrimidinyl group, the imidazopyrimidinyl group, the pyrazolopyrimidinyl group, the triazolopyrimidinyl group, the pyrrolopyrazinyl group, the imidazopyrazinyl group, the pyrazolopyrazinyl group, or the triazolopyrazinyl group , where R3 is optionally substituted by 0 to 5 (provided that when there are two or more substituted R3, each R3 represents an independent substituent),
The quinolyl group, the isoquinolyl group, the cinolyl group, the phthalazinyl group, the quinoxalinyl group, the quinazolinyl group, or the naphthyridinyl group is optionally substituted with 0 to 6 R3 (provided that when there are 2 or more R3 substitutions, Each R3 represents an independent substituent.),
The nitrogen-containing heterocyclic compound or a salt thereof according to claim 1. R1 is
cyano group,
a C1-C6 alkyl group optionally substituted with a substituent A,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with a substituent A,
a C2-C6 alkenyl group optionally substituted with a substituent A,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted with a substituent A,
or represents a C2-C6 haloalkynyl group;
R2 is
a C1-C6 alkyl group optionally substituted with a substituent A,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with a substituent A,
a C1-C6 alkoxy group optionally substituted with a substituent A,
a C1-C6 haloalkoxy group,
a C3-C8 cycloalkoxy group optionally substituted with a substituent A;
RaRbN- (wherein Ra and Rb are each independently a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, or a C3-C8 cyclo an alkyl group, or Ra and Rb together with the attached nitrogen atom form an aziridinyl group, azetidinyl group, pyrrolidinyl group, piperidinyl group, homopiperidinyl group, or azocanyl group),
Rx1C(=O)-(wherein Rx1 is a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or RaRbN- (wherein Ra and Rb are as defined above.),
phenyl group, pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, tetrazinyl group, thienyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, thiatriazolyl group, pyrrolyl group, pyrazolyl group, imidazolyl group, triazolyl group, tetrazolyl group , a pentazolyl group, a furyl group, an oxazolyl group, an isoxazolyl group, or an oxadiazolyl group,
the phenyl group is optionally substituted with 0 to 5 R3 (provided that when there are two or more substituted R3, each R3 represents an independent substituent);
The pyridyl group, the pyridazinyl group, the pyrimidinyl group, the pyrazinyl group, the triazinyl group, or the tetrazinyl group is optionally substituted with 0 to 4 R3s (provided that when there are two or more R3s, each R3 is independently represents a substituent that has
The thienyl group, the thiazolyl group, the isothiazolyl group, the thiadiazolyl group, or the thiatriazolyl group is optionally substituted by 0 to 3 R3 (provided that when there are two or more substituted R3, each R3 is an independent substituent. show.),
The pyrrolyl group, the pyrazolyl group, the imidazolyl group, the triazolyl group, the tetrazolyl group, or the pentazolyl group is optionally substituted with 0 to 4 R3 (provided that when there are two or more R3 substituted, each R3 is independently represents a substituent that has
the furyl group, the oxazolyl group, the isoxazolyl group, or the oxadiazolyl group is optionally substituted with 0 to 3 R3 (provided that when there are two or more substituted R3, each R3 represents an independent substituent);
R3 is
hydroxyl group,
cyano group,
halogen atom,
a C1 to C6 alkyl group optionally substituted with a substituent C,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with a substituent C,
a C2-C6 alkenyl group optionally substituted with a substituent C,
a C2-C6 alkynyl group optionally substituted with a substituent C,
a C1-C6 alkoxy group optionally substituted with a substituent C,
a C1-C6 haloalkoxy group,
a C3-C8 cycloalkoxy group optionally substituted with a substituent C,
a C2-C6 alkenyloxy group optionally substituted with a substituent C,
a C2-C6 haloalkenyloxy group,
a C3-C6 alkynyloxy group optionally substituted with a substituent C,
or represents a C3-C6 haloalkynyloxy group;
Y is
phenyl group,
or represents a pyridyl group,
the phenyl group is substituted with R4 at the ortho position and further optionally substituted with 0 to 4 R5 (provided that when there are two or more substituted R5, each R5 represents an independent substituent);
The pyridyl group is substituted with R4 at the ortho position, and further optionally substituted with 0 to 3 R5 (provided that when there are two or more substituted R5, each R5 represents an independent substituent),
R4 is
halogen atom,
a C1 to C6 alkyl group optionally substituted with a substituent C,
a C1-C6 haloalkyl group,
a C1-C6 alkoxy group optionally substituted with a substituent C,
or represents a C1-C6 haloalkoxy group,
R5 is
hydroxyl group,
cyano group,
halogen atom,
a C1 to C6 alkyl group optionally substituted with a substituent C,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with a substituent C,
a C2-C6 alkenyl group optionally substituted with a substituent C,
a C2-C6 alkynyl group optionally substituted with a substituent C,
a C1-C6 alkoxy group optionally substituted with a substituent C,
a C1-C6 haloalkoxy group,
a C3-C8 cycloalkoxy group optionally substituted with a substituent C,
a C2-C6 alkenyloxy group optionally substituted with a substituent C,
a C3-C6 alkynyloxy group optionally substituted with a substituent C,
a heteroaryl group optionally substituted with a substituent D,
Rc-L- (wherein Rc represents a C1-C6 alkyl group or a C1 _- C6 haloalkyl group, and L represents S, SO, or SO2),
or Rx1C (=O) O- (where Rx1 is as defined above),
R6 is
hydrogen atom,
halogen atom,
a C1-C6 alkyl group optionally substituted with a substituent A,
a C3-C8 cycloalkyl group optionally substituted with a C1-C6 haloalkyl group substituent A,
a C1-C6 alkoxy group optionally substituted with a substituent A,
or represents a C1-C6 haloalkoxy group,
R7 is
hydrogen atom,
halogen atom,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with a substituent A,
a C1-C6 alkoxy group optionally substituted with a substituent A,
or represents a C1-C6 haloalkoxy group,
The nitrogen-containing heterocyclic compound or a salt thereof according to claim 2. R1 is
a C1-C6 alkyl group optionally substituted with a substituent A,
or represents a C1-C6 haloalkyl group;
R2 is
a C1-C6 alkyl group optionally substituted with a substituent A,
a C1-C6 haloalkyl group,
Rx1C(=O)-(wherein Rx1 is a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or RaRbN- (wherein Ra and Rb are as defined above.),
or represents a phenyl group,
the phenyl group is optionally substituted with 0 to 5 R3 (provided that when there are two or more substituted R3, each R3 represents an independent substituent);
R3 is
halogen atom,
a C1 to C6 alkyl group optionally substituted with a substituent C,
or represents a C1-C6 alkoxy group optionally substituted with a substituent C;
Y is
represents a phenyl group,
the phenyl group is substituted with R4 at the ortho position and further optionally substituted with 0 to 4 R5 (provided that when there are two or more substituted R5, each R5 represents an independent substituent);
R4 is
halogen atom,
a C1 to C6 alkyl group optionally substituted with a substituent C,
or represents a C1-C6 alkoxy group optionally substituted with a substituent C,
R5 is
cyano group,
halogen atom,
a C1-C6 alkoxy group optionally substituted with a substituent C,
or represents a C1-C6 haloalkoxy group;
R6 is
hydrogen atom,
halogen atom,
a C1-C6 alkyl group optionally substituted with a substituent A,
or represents a C1-C6 haloalkyl group,
R7 is
hydrogen atom,
or represents a halogen atom,
The nitrogen-containing heterocyclic compound or a salt thereof according to claim 3. An agricultural and horticultural pesticide containing the compound according to claim 1 or a salt thereof as an active ingredient. An agricultural or horticultural fungicide containing the compound according to claim 1 or a salt thereof as an active ingredient. A method for controlling plant diseases, which comprises applying the agricultural and horticultural pest control agent according to claim 5 to plants, plant seeds, or soil for cultivating plants. A method for controlling plant diseases, which comprises applying the agricultural and horticultural fungicide according to claim 6 to plants, plant seeds, or soil for cultivating plants.