JP7370998B2 - Pyridone compounds and agricultural and horticultural fungicides containing them as active ingredients - Google Patents

Description

The present invention relates to a pyridone compound and an agricultural chemical containing the compound as an active ingredient.

Controlling diseases in agricultural and horticultural crops plays an important role in ensuring stable agricultural production. For this reason, various fungicides are used, but as long-term use of fungicides has led to the emergence of drug-resistant bacteria, there is an urgent need for new fungicides that are effective against not only drug-susceptible bacteria but also drug-resistant bacteria. has been done.

By the way, precedent examples regarding 1,3,5,6-substituted-2-pyridone compounds are known. For example, 1,3,5,6-substituted-2-pyridone compounds having an aryl group or a heteroaryl group at the 3-position have been disclosed as GABA alpha 2/3 ligands (for example, WO 98/55480 reference). As therapeutic agents for bacterial infections, 1,3,5,6-substituted-2-pyridone compounds having a carboxyl group at the 3-position have been disclosed (see, for example, European Patent No. 0308020). Furthermore, 1,3,5,6-substituted-2-pyridone compounds in which 4,4-dimethylpentanoic acid is introduced at the 1-position have been disclosed as anti-HIV agents (for example, WO 2016/012913 reference).

International Publication No. 98/55480 European Patent Specification No. 0308020 International Publication No. 2016/12913

However, the uses of the compounds described in International Publication No. 98/55480, European Patent No. 0308020, and International Publication No. 2016/12913 are all related to medicine, and the use of the agricultural and horticultural sterilizers according to the present invention is This is different from the technical field to which the agent 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 problems, the present inventors conducted intensive studies on 1,3,5,6-substituted-2-pyridone compounds. As a result, it was found that a new group of compounds in which pyrazole was introduced at the 5th position of the 2-pyridone skeleton exhibited control activity against plant diseases. Surprisingly, it was discovered that a group of compounds having a substituted pyrazole has significantly improved pesticidal activity compared to a group of compounds having an unsubstituted pyrazole, leading to the completion of the present invention.

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、モルホリル基、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およびＲ３は、それぞれ独立していて、
ハロゲン原子、
水酸基、
シアノ基、
ニトロ基、
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、
ＲｄＣ（＝Ｏ）－（ここで、Ｒｄ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。）を表す。）、
ＲｄＣ（＝Ｏ）Ｏ－（ここで、Ｒｄ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。）、
ＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）、
またはＲｅＣ（＝Ｏ）Ｎ（Ｒｆ）－（ここで、Ｒｅ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、Ｒｆ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。）を表し；
ｎは、０～４の整数（ｎが２以上の場合、２置換以上のＲ３は、それぞれ独立した置換基を表す。）を表し；
Ｒ４は、
ハロゲン原子、
シアノ基、
ニトロ基、
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、
Ｒｃ－Ｌ－（ここで、ＲｃおよびＬは、前記と同義である。）、
ＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）、
またはＲｇＣ（＝Ｏ）－（ここで、Ｒｇは水素原子、水酸基、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；
Ｒ５は、
ハロゲン原子、
シアノ基、
ニトロ基、
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、
ＲｄＣ（＝Ｏ）－（ここで、Ｒｄは、前記と同義である。）、
ＲｄＣ（＝Ｏ）Ｏ－（ここで、Ｒｄ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。）、
ＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）、
ＲｅＣ（＝Ｏ）Ｎ（Ｒｆ）－（ここで、ＲｅおよびＲｆは、前記と同義である。）、
ＲｈＯＮ＝Ｃ（Ｒｉ）－（ここで、ＲｈおよびＲｉは、それぞれ独立していて、水素原子またはＣ１～Ｃ６のアルキル基を表す。）、
または置換基Ｄで適宜０～５置換されてもよいフェニル基（ただし、２置換以上の置換基Ｄの場合、それぞれ独立している。）を表し；
ｍは、１～２の整数（ｍが２の場合、２置換のＲ５は、それぞれ独立している。）を表し；
Ｘは、酸素原子または硫黄原子を表し；
破線部を含む結合は、二重結合、または単結合を表し；
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。）、ＲｄＣ（＝Ｏ）－（ここで、Ｒｄは、前記と同義である。）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、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、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種である。］で表される化合物、またはその塩。
［２］
Ｒ１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Ｃ１～Ｃ６のアルコキシ基、
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、モルホリル基、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およびＲ３は、それぞれ独立していて、
ハロゲン原子、
水酸基、
シアノ基、
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Ｃ２～Ｃ６のアルケニル基、
置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
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Ｃ２～Ｃ６の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、
または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。）を表し；
Ｒ４は、
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Ｃ２～Ｃ６のアルケニル基、
置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
またはＲｇＣ（＝Ｏ）－（ここで、Ｒｇは水素原子、水酸基、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；
Ｒ５は、
ハロゲン原子、
シアノ基、
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、
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、
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、
ＲｄＣ（＝Ｏ）－（ここで、Ｒｄ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。）を表す。）、
Ｒｃ－Ｌ－（ここで、ＲｃおよびＬは、前記と同義である。）、
ＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）、
ＲｈＯＮ＝Ｃ（Ｒｉ）－（ここで、ＲｈおよびＲｉは、それぞれ独立していて、水素原子またはＣ１～Ｃ６のアルキル基を表す。）、
または置換基Ｄで適宜０～５置換されてもよいフェニル基（ただし、２置換以上の置換基Ｄの場合、それぞれ独立している。）を表す、［１］に記載の化合物、またはその塩。
［３］
Ｒ１は、
置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
またはＣ１～Ｃ６のハロアルキル基を表し；
Ｒ２およびＲ３は、それぞれ独立していて、
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、
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。）を表し；
Ｒ４は、
ハロゲン原子を表し；
Ｒ５は、
ハロゲン原子、
シアノ基、
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、
置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
ＲｄＣ（＝Ｏ）－（ここで、Ｒｄ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、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、モルホリル基、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。）を表す。）、
Ｒｃ－Ｌ－（ここで、ＲｃおよびＬは、前記と同義である。）、
ＲｈＯＮ＝Ｃ（Ｒｉ）－（ここで、ＲｈおよびＲｉは、それぞれ独立していて、水素原子またはＣ１～Ｃ６のアルキル基を表す。）、
または置換基Ｄで適宜０～５置換されてもよいフェニル基（ただし、２置換以上の置換基Ｄの場合、それぞれ独立している。）を表し、
Ｘは、酸素原子を表し；
破線部を含む結合は、二重結合を表す、［２］に記載の化合物、またはその塩。
［４］
Ｒ１は、
Ｃ１～Ｃ６のアルキル基、またはＣ１～Ｃ６のハロアルキル基を表す、［１］～［３］のいずれか１つに記載の化合物、またはその塩。
［５］
Ｒ１は、
メチル基、エチル基、または２，２－ジフルオロエチル基を表す、［１］～［３］のいずれか１つに記載の化合物、またはその塩。
［６］
Ｒ２およびＲ３は、それぞれ独立していて、
ハロゲン原子、Ｃ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のアルコキシ基、または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。）を表す、［１］～［５］のいずれか１つに記載の化合物、またはその塩。
［７］
Ｒ２およびＲ３は、それぞれ独立していて、
フッ素原子、塩素原子、メチル基、メトキシ基、メチルチオ基、メタンスルフィニル基、またはメタンスルホニル基を表す、［１］～［５］のいずれか１つに記載の化合物、またはその塩。
［８］
式（１）における部分構造のＰｈ

が、２－フルオロフェニル基、２－クロロフェニル基、２－クロロ－４－フルオロフェニル基、２－クロロ－６－フルオロフェニル基、２，４－ジフルオロフェニル基、２，６－ジフルオロフェニル基、２，４，６－トリフルオロフェニル基、２－フルオロ－４－メチルフェニル基、２－フルオロ－４－メトキシフェニル基、２－フルオロ－４－（メチルチオ）フェニル基、２－フルオロ－４－（メタンスルフィニル）フェニル基、または２－フルオロ－４－（メタンスルホニル）フェニル基である、［１］～［５］のいずれか１つに記載の化合物、またはその塩。
［９］
Ｒ４は、
塩素原子、または臭素原子を表す、［１］～［８］のいずれか１つに記載の化合物、またはその塩。
［１０］
Ｒ５は、
ハロゲン原子、シアノ基、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、Ｃ３～Ｃ８のシクロアルキル基、Ｃ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のアルキニル基、Ｃ１～Ｃ６のアルコキシ基、ＲｄＣ（＝Ｏ）－（ここで、Ｒｄ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、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、モルホリル基、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。）を表す。）、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。）、ＲｈＯＮ＝Ｃ（Ｒｉ）－（ここで、ＲｈおよびＲｉは、それぞれ独立していて、水素原子またはＣ１～Ｃ６のアルキル基を表す。）、またはフェニル基を表す、［１］～［９］のいずれか１つに記載の化合物、またはその塩。
［１１］
Ｒ５は、
塩素原子、臭素原子、ヨウ素原子、シアノ基、メチル基、エチル基、プロピル基、イソプロピル基、イソブチル基、ｔ－ブチル基、１－ヒドロキシエチル基、トリフルオロメチル基、シクロプロピル基、ビニル基、２－メチルプロペン－１－イル基、エチニル基、メトキシ基、ホルミル基、エトキシカルボニル基、メチルチオ基、（メトキシイミノ）メチル基、またはフェニル基を表す、［１］～［９］のいずれか１つに記載の化合物、またはその塩。
［１２］
式（１）における部分構造のＡｚ

が、５－クロロ－１H－ピラゾール－１－イル、５－ブロモ－１H－ピラゾール－１－イル、５－ヨード－１H－ピラゾール－１－イル、５－シアノ－１H－ピラゾール－１－イル、３－メチル－１H－ピラゾール－１－イル、５－メチル－１H－ピラゾール－１－イル、５－エチル－１H－ピラゾール－１－イル、５－プロピル－１H－ピラゾール－１－イル、５－イソプロピル－１H－ピラゾール－１－イル、５－イソブチル－１H－ピラゾール－１－イル、５－（t-ブチル）－１H－ピラゾール－１－イル、５－（１－ヒドロキシエチル）－１H－ピラゾール－１－イル、３，５－ジメチル－１H－ピラゾール－１－イル、５－エチル－3-メチル－１H－ピラゾール－１－イル、５－イソプロピル－3-メチル－１H－ピラゾール－１－イル、５－(t-ブチル)－3-メチル－１H－ピラゾール－１－イル、３，５－ジエチル－１H－ピラゾール－１－イル、５－(t-ブチル)－3-エチル－１H－ピラゾール－１－イル、５－クロロ－３－メチル－１H－ピラゾール－１－イル、５－ブロモ－３－メチル－１H－ピラゾール－１－イル、５－（トリフルオロメチル）－１H－ピラゾール－１－イル、３，５－ジ（トリフルオロメチル）－１H－ピラゾール－１－イル、３－メチル－５－（トリフルオロメチル）－１H－ピラゾール－１－イル、５－シクロプロピル－１H－ピラゾール－１－イル、５－シクロプロピル－3－メチル－１H－ピラゾール－１－イル、５－ビニル－１H－ピラゾール－１－イル、５－（２－メチルプロペン－１－イル）－１H－ピラゾール－１－イル、５－エチニル－１H－ピラゾール－１－イル、５－メトキシ－１H－ピラゾール－１－イル、５－ホルミル－１H－ピラゾール－１－イル、３－エトキシカルボニル－５－メチル－１H－ピラゾール－１－イル、５－エトキシカルボニル－３－メチル－１H－ピラゾール－１－イル、５－（メチルチオ）－１H－ピラゾール－１－イル、５－（（メトキシイミノ）メチル）－１H－ピラゾール－１－イル、５－フェニル－１H－ピラゾール－１－イル、または３－メチル－５－フェニル－１H－ピラゾール－１－イルである、［１］～［９］のいずれか１つに記載の化合物、またはその塩。
［１３］
［１］～［１２］のいずれか１つに記載の化合物、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。
［１４］
［１］～［１２］のいずれか１つに記載の化合物、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。
［１５］
［１３］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。
［１６］
［１４］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。[1]
Formula (1)

[In the formula,
R1 is
hydroxyl group,
cyano group,
C1 to C6 alkyl group which may be optionally substituted with substituent A,
C1 to C6 haloalkyl group,
C3 to C8 cycloalkyl group optionally substituted with substituent A,
C2 to C6 alkenyl group optionally substituted with substituent A,
C2-C6 haloalkenyl group,
C2 to C6 alkynyl group optionally substituted with substituent A,
C2-C6 haloalkynyl group,
C1 to C6 alkoxy group which may be optionally substituted with substituent A,
C1 to C6 haloalkoxy group,
C3 to C8 cycloalkoxy group which may be optionally substituted with substituent A,
C2 to C6 alkenyloxy group optionally substituted with substituent A,
C2-C6 haloalkenyloxy group,
a C3 to C6 alkynyloxy group which may be optionally substituted with substituent A;
C3 to C6 haloalkynyloxy group,
or RaRbN- (where Ra and Rb are each independently a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent B, a C1-C6 haloalkyl group, or a C3-C8 haloalkyl group) Ra and Rb represent a cycloalkyl group, or together with the nitrogen atom to which they are bonded, form an aziridinyl group, azetidinyl group, pyrrolidinyl group, piperidinyl group, morpholyl group, homopiperidinyl group, or azocanyl group .) represents;
R2 and R3 are each independent,
halogen atom,
hydroxyl group,
cyano group,
nitro group,
C1 to C6 alkyl group which may be optionally substituted with substituent C,
C1 to C6 haloalkyl group,
C3 to C8 cycloalkyl group which may be optionally substituted with substituent C,
C2 to C6 alkenyl group optionally substituted with substituent C,
C2-C6 haloalkenyl group,
a C2 to C6 alkynyl group which may be optionally substituted with substituent C;
C2-C6 haloalkynyl group,
C1 to C6 alkoxy group which may be optionally substituted with substituent C,
C1 to C6 haloalkoxy group,
C3 to C8 cycloalkoxy group which may be optionally substituted with substituent C,
C2 to C6 alkenyloxy group optionally substituted with substituent C,
C2-C6 haloalkenyloxy group,
a C3 to C6 alkynyloxy group which may be optionally substituted with substituent C;
C3 to C6 haloalkynyloxy group,
RdC(=O)-(wherein, Rd is a hydrogen atom, a C1 to C6 alkyl group which may be optionally substituted with substituent B, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group, a C1 to C8 cycloalkyl group, represents a C6 alkoxy group, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group, or RaRbN- (where Ra and Rb have the same meanings as above),
RdC(=O)O- (here, Rd has the same meaning as above),
Rc-L- (where Rc represents a C1 to C6 alkyl group or a C1 to C6 haloalkyl group, and L represents S, SO, or SO ₂ ),
RaRbN- (where Ra and Rb have the same meanings as above),
or ReC(=O)N(Rf)- (where Re is a hydrogen atom, a C1 to C6 alkyl group which may be optionally substituted with substituent B, a C1 to C6 haloalkyl group, a C3 to C8 cyclo Represents an alkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or RaRbN- (where Ra and Rb have the same meanings as above), and Rf is , represents a hydrogen atom, a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, or a C3 to C8 cycloalkyl group, which may be optionally substituted with a substituent B);
n represents an integer of 0 to 4 (when n is 2 or more, R3 of 2 or more substitutions each represents an independent substituent);
R4 is
halogen atom,
cyano group,
nitro group,
C1 to C6 alkyl group which may be optionally substituted with substituent A,
C1 to C6 haloalkyl group,
C3 to C8 cycloalkyl group optionally substituted with substituent A,
C2 to C6 alkenyl group optionally substituted with substituent A,
C2-C6 haloalkenyl group,
C2 to C6 alkynyl group optionally substituted with substituent A,
C2-C6 haloalkynyl group,
C1 to C6 alkoxy group which may be optionally substituted with substituent A,
C1 to C6 haloalkoxy group,
C3 to C8 cycloalkoxy group which may be optionally substituted with substituent A,
C2 to C6 alkenyloxy group optionally substituted with substituent A,
C2-C6 haloalkenyloxy group,
a C3 to C6 alkynyloxy group which may be optionally substituted with substituent A;
C3 to C6 haloalkynyloxy group,
Rc-L- (where Rc and L have the same meanings as above),
RaRbN- (where Ra and Rb have the same meanings as above),
or RgC(=O)- (where Rg is a hydrogen atom, a hydroxyl group, a C1 to C6 alkyl group that may be optionally substituted with substituent B, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group, represents a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group, or RaRbN- (where Ra and Rb have the same meanings as above);
R5 is
halogen atom,
cyano group,
nitro group,
C1 to C6 alkyl group which may be optionally substituted with substituent C,
C1 to C6 haloalkyl group,
C3 to C8 cycloalkyl group which may be optionally substituted with substituent C,
C2 to C6 alkenyl group optionally substituted with substituent C,
C2-C6 haloalkenyl group,
a C2 to C6 alkynyl group which may be optionally substituted with substituent C;
C2-C6 haloalkynyl group,
C1 to C6 alkoxy group which may be optionally substituted with substituent C,
C1 to C6 haloalkoxy group,
C3 to C8 cycloalkoxy group which may be optionally substituted with substituent C,
C2 to C6 alkenyloxy group optionally substituted with substituent C,
C2-C6 haloalkenyloxy group,
a C3 to C6 alkynyloxy group which may be optionally substituted with substituent C;
C3 to C6 haloalkynyloxy group,
RdC(=O)-(here, Rd has the same meaning as above),
RdC(=O)O- (here, Rd has the same meaning as above),
Rc-L- (where Rc and L have the same meanings as above),
RaRbN- (where Ra and Rb have the same meanings as above),
ReC(=O)N(Rf)-(Here, Re and Rf have the same meanings as above.),
RhON=C(Ri)- (where Rh and Ri each independently represent a hydrogen atom or a C1 to C6 alkyl group),
or a phenyl group that may be optionally substituted with 0 to 5 substituents D (however, in the case of two or more substituents D, each is independent);
m represents an integer of 1 to 2 (when m is 2, each of the two substituted R5s is independent);
X represents an oxygen atom or a sulfur atom;
Bonds containing broken lines represent double bonds or single bonds;
Substituent A 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- (where Rc and L are as defined above);
Substituent B is 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;
Substituent C is a hydroxyl group, a cyano group, a C3 to C8 cycloalkyl group, a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group, a C2 to C6 alkoxyalkoxy group, RaRbN -(Here, Ra and Rb have the same meanings as above.), Rc-L-(Here, Rc and L have the same meanings as above.), RdC(=O)-(Here, Rd is as defined above) and at least one member selected from the group consisting of a 3- to 6-membered ring group containing 1 to 2 oxygen atoms;
Substituent D is a hydroxyl group, a cyano group, a halogen atom, a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, a C1 to C6 alkoxy group, RaRbN- (where Ra and Rb are as defined above) ) and Rc-L- (where Rc and L have the same meanings as above). ] or its salt.
[2]
R1 is
C1 to C6 alkyl group which may be optionally substituted with substituent A,
C1 to C6 haloalkyl group,
C2 to C6 alkenyl group optionally substituted with substituent A,
C2-C6 haloalkenyl group,
C1 to C6 alkoxy group which may be optionally substituted with substituent A,
or RaRbN- (where Ra and Rb are each independently a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent B, a C1-C6 haloalkyl group, or a C3-C8 haloalkyl group) Ra and Rb represent a cycloalkyl group, or together with the nitrogen atom to which they are bonded, form an aziridinyl group, azetidinyl group, pyrrolidinyl group, piperidinyl group, morpholyl group, homopiperidinyl group, or azocanyl group .) represents;
R2 and R3 are each independent,
halogen atom,
hydroxyl group,
cyano group,
C1 to C6 alkyl group which may be optionally substituted with substituent C,
C1 to C6 haloalkyl group,
C2 to C6 alkenyl group optionally substituted with substituent C,
a C2 to C6 alkynyl group which may be optionally substituted with substituent C;
C1 to C6 alkoxy group which may be optionally substituted with substituent C,
C1 to C6 haloalkoxy group,
C2 to C6 alkenyloxy group optionally substituted with substituent C,
a C3 to C6 alkynyloxy group which may be optionally substituted with substituent C;
or Rc-L- (where Rc represents a C1 to C6 alkyl group or a C1 to C6 haloalkyl group, and L represents S, SO, or SO ₂ );
R4 is
halogen atom,
C1 to C6 alkyl group which may be optionally substituted with substituent A,
C1 to C6 haloalkyl group,
C2 to C6 alkenyl group optionally substituted with substituent A,
C2 to C6 alkynyl group optionally substituted with substituent A,
C1 to C6 alkoxy group which may be optionally substituted with substituent A,
or RgC(=O)- (where Rg is a hydrogen atom, a hydroxyl group, a C1 to C6 alkyl group that may be optionally substituted with substituent B, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group, represents a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group, or RaRbN- (where Ra and Rb have the same meanings as above);
R5 is
halogen atom,
cyano group,
C1 to C6 alkyl group which may be optionally substituted with substituent C,
C1 to C6 haloalkyl group,
C3 to C8 cycloalkyl group which may be optionally substituted with substituent C,
C2 to C6 alkenyl group optionally substituted with substituent C,
C2-C6 haloalkenyl group,
a C2 to C6 alkynyl group which may be optionally substituted with substituent C;
C2-C6 haloalkynyl group,
C1 to C6 alkoxy group which may be optionally substituted with substituent C,
C2 to C6 alkenyloxy group optionally substituted with substituent C,
a C3 to C6 alkynyloxy group which may be optionally substituted with substituent C;
RdC(=O)-(wherein, Rd is a hydrogen atom, a C1 to C6 alkyl group which may be optionally substituted with substituent B, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group, a C1 to C8 cycloalkyl group, represents a C6 alkoxy group, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group, or RaRbN- (where Ra and Rb have the same meanings as above),
Rc-L- (where Rc and L have the same meanings as above),
RaRbN- (where Ra and Rb have the same meanings as above),
RhON=C(Ri)- (where Rh and Ri each independently represent a hydrogen atom or a C1 to C6 alkyl group),
or the compound according to [1], or a salt thereof, which represents a phenyl group that may be optionally substituted with 0 to 5 substituents D (however, in the case of two or more substituents D, each is independent); .
[3]
R1 is
C1 to C6 alkyl group which may be optionally substituted with substituent A,
or represents a C1 to C6 haloalkyl group;
R2 and R3 are each independent,
halogen atom,
C1 to C6 alkyl group which may be optionally substituted with substituent C,
C1 to C6 alkoxy group which may be optionally substituted with substituent C,
or Rc-L- (where Rc represents a C1 to C6 alkyl group or a C1 to C6 haloalkyl group, and L represents S, SO, or SO ₂ );
R4 is
Represents a halogen atom;
R5 is
halogen atom,
cyano group,
C1 to C6 alkyl group which may be optionally substituted with substituent C,
C1 to C6 haloalkyl group,
C3 to C8 cycloalkyl group which may be optionally substituted with substituent C,
C2 to C6 alkenyl group optionally substituted with substituent C,
a C2 to C6 alkynyl group which may be optionally substituted with substituent C;
C1 to C6 alkoxy group which may be optionally substituted with substituent C,
RdC(=O)-(wherein, Rd is a hydrogen atom, a C1 to C6 alkyl group which may be optionally substituted with substituent B, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group, a C1 to C8 cycloalkyl group, C6 alkoxy group, C1 to C6 haloalkoxy group, C3 to C8 cycloalkoxy group, or RaRbN- (where Ra and Rb are each independently substituted with a hydrogen atom or substituent B) may represent a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group, or Ra and Rb, together with the nitrogen atom to which they are bonded, represent an aziridinyl group, an azetidinyl group, represents a group that forms a pyrrolidinyl group, piperidinyl group, morpholyl group, homopiperidinyl group, or azocanyl group),
Rc-L- (where Rc and L have the same meanings as above),
RhON=C(Ri)- (where Rh and Ri each independently represent a hydrogen atom or a C1 to C6 alkyl group),
or a phenyl group which may be optionally substituted with 0 to 5 substituents D (however, in the case of two or more substituents D, each is independent),
X represents an oxygen atom;
The compound according to [2], or a salt thereof, wherein the bond containing the broken line represents a double bond.
[4]
R1 is
The compound according to any one of [1] to [3], or a salt thereof, which represents a C1 to C6 alkyl group or a C1 to C6 haloalkyl group.
[5]
R1 is
The compound according to any one of [1] to [3], or a salt thereof, which represents a methyl group, an ethyl group, or a 2,2-difluoroethyl group.
[6]
R2 and R3 are each independent,
A halogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, or Rc-L- (where Rc represents a C1-C6 alkyl group or a C1-C6 haloalkyl group, and L represents S, The compound according to any one of [1] to [5], or a salt thereof, which represents SO or SO ₂ .
[7]
R2 and R3 are each independent,
The compound according to any one of [1] to [5], or a salt thereof, which represents a fluorine atom, a chlorine atom, a methyl group, a methoxy group, a methylthio group, a methanesulfinyl group, or a methanesulfonyl group.
[8]
Ph of the partial structure in formula (1)

is a 2-fluorophenyl group, 2-chlorophenyl group, 2-chloro-4-fluorophenyl group, 2-chloro-6-fluorophenyl group, 2,4-difluorophenyl group, 2,6-difluorophenyl group, 2 , 4,6-trifluorophenyl group, 2-fluoro-4-methylphenyl group, 2-fluoro-4-methoxyphenyl group, 2-fluoro-4-(methylthio)phenyl group, 2-fluoro-4-(methane The compound according to any one of [1] to [5], or a salt thereof, which is a sulfinyl) phenyl group or a 2-fluoro-4-(methanesulfonyl) phenyl group.
[9]
R4 is
The compound according to any one of [1] to [8], or a salt thereof, representing a chlorine atom or a bromine atom.
[10]
R5 is
Halogen atom, cyano group, C1-C6 alkyl group optionally substituted with substituent C, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C2-C6 alkenyl group, C2-C6 alkynyl group group, a C1 to C6 alkoxy group, RdC(=O)- (where Rd is a hydrogen atom, a C1 to C6 alkyl group which may be optionally substituted with substituent B, a C1 to C6 haloalkyl group, a C3 -C8 cycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group, or RaRbN- (where Ra and Rb are each independently hydrogen atom , represents a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group, which may be optionally substituted with a substituent B, or Ra and Rb, together with the bonding nitrogen atom, ), Rc-L- (where Rc is C1- represents a C6 alkyl group or a C1 to C6 haloalkyl group, L represents S, SO, or SO ₂ ), RhON=C(Ri)- (wherein Rh and Ri are each independently , a hydrogen atom or a C1-C6 alkyl group), or a phenyl group, or a salt thereof according to any one of [1] to [9].
[11]
R5 is
Chlorine atom, bromine atom, iodine atom, cyano group, methyl group, ethyl group, propyl group, isopropyl group, isobutyl group, t-butyl group, 1-hydroxyethyl group, trifluoromethyl group, cyclopropyl group, vinyl group, Any one of [1] to [9] representing a 2-methylpropen-1-yl group, ethynyl group, methoxy group, formyl group, ethoxycarbonyl group, methylthio group, (methoxyimino)methyl group, or phenyl group or a salt thereof.
[12]
Az of the partial structure in formula (1)

is 5-chloro-1H-pyrazol-1-yl, 5-bromo-1H-pyrazol-1-yl, 5-iodo-1H-pyrazol-1-yl, 5-cyano-1H-pyrazol-1-yl, 3-Methyl-1H-pyrazol-1-yl, 5-methyl-1H-pyrazol-1-yl, 5-ethyl-1H-pyrazol-1-yl, 5-propyl-1H-pyrazol-1-yl, 5- Isopropyl-1H-pyrazol-1-yl, 5-isobutyl-1H-pyrazol-1-yl, 5-(t-butyl)-1H-pyrazol-1-yl, 5-(1-hydroxyethyl)-1H-pyrazole -1-yl, 3,5-dimethyl-1H-pyrazol-1-yl, 5-ethyl-3-methyl-1H-pyrazol-1-yl, 5-isopropyl-3-methyl-1H-pyrazol-1-yl , 5-(t-butyl)-3-methyl-1H-pyrazol-1-yl, 3,5-diethyl-1H-pyrazol-1-yl, 5-(t-butyl)-3-ethyl-1H-pyrazole -1-yl, 5-chloro-3-methyl-1H-pyrazol-1-yl, 5-bromo-3-methyl-1H-pyrazol-1-yl, 5-(trifluoromethyl)-1H-pyrazol-1 -yl, 3,5-di(trifluoromethyl)-1H-pyrazol-1-yl, 3-methyl-5-(trifluoromethyl)-1H-pyrazol-1-yl, 5-cyclopropyl-1H-pyrazole -1-yl, 5-cyclopropyl-3-methyl-1H-pyrazol-1-yl, 5-vinyl-1H-pyrazol-1-yl, 5-(2-methylpropen-1-yl)-1H-pyrazole -1-yl, 5-ethynyl-1H-pyrazol-1-yl, 5-methoxy-1H-pyrazol-1-yl, 5-formyl-1H-pyrazol-1-yl, 3-ethoxycarbonyl-5-methyl- 1H-pyrazol-1-yl, 5-ethoxycarbonyl-3-methyl-1H-pyrazol-1-yl, 5-(methylthio)-1H-pyrazol-1-yl, 5-((methoxyimino)methyl)-1H - Any one of [1] to [9] which is pyrazol-1-yl, 5-phenyl-1H-pyrazol-1-yl, or 3-methyl-5-phenyl-1H-pyrazol-1-yl or a salt thereof.
[13]
An agricultural and horticultural pest control agent containing the compound according to any one of [1] to [12] or a salt thereof as an active ingredient.
[14]
An agricultural and horticultural fungicide containing the compound according to any one of [1] to [12] or a salt thereof as an active ingredient.
[15]
A method for controlling plant diseases, which comprises applying the agricultural and horticultural pest control agent according to [13] to plants, plant seeds, or soil in which plants are grown.
[16]
A method for controlling plant diseases, which comprises applying the agricultural and horticultural fungicide according to [14] to plants, plant seeds, or soil in which plants are grown.

According to the present invention, it is possible to provide a novel compound that is effective as a fungicide for agriculture and horticulture.

EMBODIMENT OF THE INVENTION Hereinafter, the form for implementing this invention is demonstrated in detail.

It should be noted that each term used in the claims and the specification shall have the definition commonly used in the technical field, unless otherwise specified.

In this specification, the abbreviations used are explained below.
DMF: N,N-dimethylformamide, THF: tetrahydrofuran, Me: methyl group, Et: ethyl group, Pr: propyl group, Bu: butyl group, Ph: phenyl group, i: iso, sec: secondary, t: tertiary, c: cyclo, =: double bond, ≡: triple bond. Regarding Pr and Bu in the columns of the table, if there is no prefix, it means normal.

Below, definitions of terms used in this specification will be explained.

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

The term "optionally substituted" means substituted or unsubstituted. When using this term, if the number of substituents is not specified, it is indicated that the number of substituents is one. On the other hand, for example, when the number of substituents is specified as "may be appropriately substituted by 0 to 5", it is understood that all integers between 0 and 5 are also individually disclosed. be done. That is, it means that the number of substituents is none, 1, 2, 3, 4, or 5 substituents.

The C1 to C6 alkyl group may be linear or branched, and specifically includes a methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, and t-butyl group. , pentyl group, isopentyl group, 1-methylbutyl group, 2-methylbutyl group, neopentyl group, 1-ethylpropyl group, 1,2-dimethylpropyl group, hexyl group, 1-methylpentyl group, 2-methylpentyl group, 3 -Methylpentyl group, 4-methylpentyl group, 1,1-dimethylbutyl group, 2,2-dimethylbutyl group, 3,3-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.

Specifically, the 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 the hydrogen atom is optionally substituted with one or more halogen atoms. When substituted with two or more halogen atoms, these halogen atoms may be the same or different, and the number of substitutions is not particularly limited as long as it can exist as a substituent. Specific examples of C1 to C6 haloalkyl groups include monofluoromethyl group, difluoromethyl group, trifluoromethyl group, monochloromethyl group, dichloromethyl group, monobromomethyl group, dibromomethyl group, monoiodomethyl group, diiodomethyl group, Chlorodifluoromethyl group, bromodifluoromethyl group, trichloromethyl group, 1-fluoroethyl group, 2-fluoroethyl group, 1,1-difluoroethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoro Ethyl 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.

Specific examples of the C3 to C8 cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group.

The C2-C6 alkenyl group represents an unsaturated hydrocarbon group that has one or more double bonds and is linear or branched. In addition, if there is a geometric isomer, it may be only one of the E-form or the Z-form, or a mixture of the E-form and the Z-form at any ratio, and there are no particular limitations as long as the number of carbon atoms is within the specified range. It never happens. Specific examples of C2 to C6 alkenyl groups include vinyl group, 1-propenyl group, allyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group. 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, Examples include 3-methyl-2-pentenyl group.

The C2-C6 haloalkenyl group represents a C2-C6 alkenyl group in which the hydrogen atom is optionally substituted with one or more halogen atoms. When substituted with two or more halogen atoms, these halogen atoms may be the same or different, and the number of substitutions is not particularly limited as long as it can exist as a substituent. 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, Examples include 3-dichloroallyl group, 4,4-difluoro-3-butenyl group, 5,5-difluoro-4-pentenyl group, and 6,6-difluoro-5-hexenyl group.

The C2-C6 alkynyl group represents an unsaturated hydrocarbon group that has one or more triple bonds and is linear or branched. Specific examples of C2 to C6 alkynyl groups include ethynyl group, 1-propynyl group, propargyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group. 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 the hydrogen atom is optionally substituted with one or more halogen atoms. When substituted with two or more halogen atoms, these halogen atoms may be the same or different, and the number of substitutions is not particularly limited as long as it can exist as a substituent. Specific examples of C2 to C6 haloalkynyl groups include 2-fluoroethynyl group, 2-chloroethynyl group, 2-bromoethynyl group, 2-iodoethynyl group, 3,3-difluoro-1-propynyl group, 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 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 group in which the above-mentioned C1-C6 alkyl groups are bonded via an oxygen atom. Specific examples of C1 to C6 alkoxy groups include methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butoxy group, isobutoxy group, sec-butoxy group, t-butoxy group, pentyloxy group, isopentyloxy group, 1-methylbutoxy group, 2-methylbutoxy group, neopentyloxy group, 1-ethylpropyloxy group, 1,2-dimethylpropyloxy group, hexyloxy group, 1-methylpentyloxy group, 2-methylpentyloxy 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. It will be done.

The C1-C6 haloalkoxy group represents a C1-C6 alkoxy group in which the hydrogen atom is optionally substituted with one or more halogen atoms. When substituted with two or more halogen atoms, these halogen atoms may be the same or different, and the number of substitutions is not particularly limited as long as it can exist as a substituent. Specific examples of C1 to C6 haloalkoxy groups include difluoromethoxy group, trifluoromethoxy group, chlorodifluoromethoxy group, bromodifluoromethoxy group, 2-fluoroethoxy group, 2,2-difluoroethoxy group, 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-trifluoroethoxy group 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 group in which the above-mentioned C3-C8 cycloalkyl groups are bonded via an oxygen atom. Specific examples of the C3 to C8 cycloalkoxy group include a cyclopropyloxy group, a cyclobutoxy group, a cyclopentyloxy group, a cyclohexyloxy group, a cycloheptyloxy group, a cyclooctyloxy group, and the like.

The C2-C6 alkenyloxy group represents a group in which the above-mentioned C2-C6 alkenyl groups are bonded via an oxygen atom. In addition, if there is a geometric isomer, it is only one of the E form or the Z form, or a mixture of the E form and the Z form at any ratio, and there are no particular restrictions as long as the number of carbon atoms is within the specified range. It never happens. Specific examples of C2 to C6 alkenyloxy groups include vinyloxy group, 1-propenyloxy group, allyloxy group, 1-butenyloxy group, 2-butenyloxy group, 3-butenyloxy group, 1-pentenyloxy group, 2-pentenyloxy group. , 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 group, 3-methyl-2-pentenyloxy group, 4-methyl-3-pentenyloxy group, and the like.

The C2-C6 haloalkenyloxy group represents a C2-C6 alkenyloxy group in which the hydrogen atom is optionally substituted with one or more halogen atoms. When substituted with two or more halogen atoms, these halogen atoms may be the same or different, and the number of substitutions is not particularly limited as long as it can exist as a substituent. Specific examples of C2 to C6 haloalkenyloxy groups include 2-fluorovinyloxy group, 2,2-difluorovinyloxy group, 2,2-dichlorovinyloxy group, 3-fluoroallyloxy group, 3,3-difluoro Examples include allyloxy group, 3,3-dichloroallyloxy group, 4,4-difluoro-3-butenyloxy group, 5,5-difluoro-4-pentenyloxy group, 6,6-difluoro-5-hexenyloxy group, etc. It will be done.

The C3-C6 alkynyloxy group refers to a C3-C6 alkynyl group bonded via an oxygen atom among the above-mentioned C2-C6 alkynyl groups. Specific examples of C3 to C6 alkynyloxy groups include propargyloxy group, 2-butynyloxy group, 3-butynyloxy group, 2-pentynyloxy group, 3-pentynyloxy group, 4-pentynyloxy group, 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 the hydrogen atom is optionally substituted with one or more halogen atoms. When substituted with two or more halogen atoms, these halogen atoms may be the same or different, and the number of substitutions is not particularly limited as long as it can exist as a substituent. Specific examples of C3 to 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, etc. It will be done.

A C2-C6 alkoxyalkoxy group is one in which the hydrogen atom in the C1-C5 alkoxy group among the above-mentioned C1-C6 alkoxy groups is optionally substituted with one or more C1-C5 alkoxy groups. represents. There is no particular limitation as long as the total number of carbons is within the specified range of carbon numbers. Specific examples of C2 to C6 alkoxyalkoxy groups include methoxymethoxy group, ethoxymethoxy group, propyloxymethoxy group, isopropyloxymethoxy group, methoxyethoxy group, ethoxyethoxy group, propyloxyethoxy group, isopropyloxyethoxy group, methoxypropyl Examples include oxy group, ethoxypropyloxy group, propyloxypropyloxy group, isopropyloxypropyloxy group, and the like.

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

The pyridone compound of the present invention includes a compound represented by the following formula (1) and a salt thereof (hereinafter also referred to as "the compound of the present invention").

Formula (1) will be explained below.

R1 in formula (1) is a hydroxyl group, a cyano group, a C1 to C6 alkyl group which may be optionally substituted with a substituent A, a C1 to C6 haloalkyl group, or a C3 to C6 which may be optionally substituted with a substituent A. C8 cycloalkyl group, C2-C6 alkenyl group optionally substituted with substituent A, C2-C6 haloalkenyl group, C2-C6 alkynyl group optionally substituted with substituent A, C2- C6 haloalkynyl group, C1 to C6 alkoxy group optionally substituted with substituent A, C1 to C6 haloalkoxy group, C3 to C8 cycloalkoxy group optionally substituted with substituent A, substitution C2-C6 alkenyloxy group optionally substituted with group A, C2-C6 haloalkenyloxy group, C3-C6 alkynyloxy group optionally substituted with substituent A, C3-C6 haloalkynyl oxy group, or RaRbN- (where Ra and Rb are each independently a hydrogen atom, a C1 to C6 alkyl group which may be optionally substituted with substituent B, a C1 to C6 haloalkyl group, or a C3 ~C8 cycloalkyl group, or Ra and Rb together with the bonding nitrogen atom form an aziridinyl group, azetidinyl group, pyrrolidinyl group, piperidinyl group, morpholyl group, homopiperidinyl group, or azocanyl group represents something).

Among them, R1 is a C1 to C6 alkyl group optionally substituted with a substituent A, a C1 to C6 haloalkyl group, a C2 to C6 alkenyl group optionally substituted with a substituent A, or a C2 to C6 halo group. An alkenyl group, a C1 to C6 alkoxy group optionally substituted with substituent A, or RaRbN- (where Ra and Rb have the same meanings as above) are preferred,
In particular, R1 is preferably a C1 to C6 alkyl group which may be optionally substituted with a substituent A, or a C1 to C6 haloalkyl group.
For example, in a preferred embodiment, R1 represents a C1-C6 alkyl group or a C1-C6 haloalkyl group.

R1 in formula (1) includes a hydroxyl group and a cyano group.
The C1 to C6 alkyl group of the "C1 to C6 alkyl group optionally substituted with substituent A" in R1 of formula (1) has the same meaning as the above definition, and is preferably a methyl group or an ethyl group. , or a propyl group, more preferably a methyl group or an ethyl group. When a substituent A is present, a hydrogen atom in a C1 to C6 alkyl group is optionally substituted with the substituent A.

The "C1 to C6 haloalkyl group" in R1 of formula (1) has the same meaning as the above definition, and is preferably a 2-fluoroethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group. 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 to C8 cycloalkyl group of the "C3 to C8 cycloalkyl group optionally substituted with substituent A" in R1 of formula (1) has the same meaning as the above definition, and is preferably a cyclopropyl group. , a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, and more preferably a cyclopropyl group or a cyclobutyl group. When a substituent A is present, a hydrogen atom in a C3 to C8 cycloalkyl group is optionally substituted with the substituent A.

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

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

The C2 to C6 alkynyl group of the "C2 to C6 alkynyl group optionally substituted with substituent A" in R1 of formula (1) has the same meaning as the above definition, and is preferably a propargyl group, a 2- A butynyl group or a 3-butynyl group, more preferably a propargyl group. When a substituent A is present, a hydrogen atom in a C2 to C6 alkynyl group is optionally substituted with the substituent A.

The "C2-C6 haloalkynyl group" in R1 of formula (1) has the same meaning as the above definition, and is preferably a 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 group. or 4,4,4-trifluoro-2-butynyl group.

The C1 to C6 alkoxy group of the "C1 to C6 alkoxy group optionally substituted with substituent A" in R1 of formula (1) has the same meaning as the above definition, and is preferably a methoxy group or an ethoxy group. , or a propyloxy group, more preferably a methoxy group or an ethoxy group. When a substituent A is present, a hydrogen atom in a C1 to C6 alkoxy group is optionally substituted with the substituent A.

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

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

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

The "C2-C6 haloalkenyloxy group" in R1 of formula (1) has the same meaning as the above definition, and is preferably a 2-fluorovinyloxy group, a 2,2-difluorovinyloxy group, a 3-fluorovinyloxy group, Allyloxy group or 3,3-difluoroallyloxy group, more preferably 2-fluorovinyloxy group or 2,2-difluorovinyloxy group.

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

The "C3 to C6 haloalkynyloxy group" in R1 of formula (1) has the same meaning as the above definition, and is preferably a 4,4-difluoro-2-butynyloxy group, a 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. -butynyloxy group or 4,4,4-trifluoro-2-butynyloxy group.

"RaRbN-" in R1 of formula (1) (where Ra and Rb are each independently a hydrogen atom, a C1 to C6 alkyl group which may be optionally substituted with substituent B, a C1 to C6 alkyl group) A haloalkyl group or a C3-C8 cycloalkyl group, or Ra and Rb together with the nitrogen atom to which they are bonded represent an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, a piperidinyl group, a morpholyl group, a homopiperidinyl group, or Each term (representing a group forming an azocanyl group) has the same meaning as defined above. Regarding the "C1 to C6 alkyl group which may be optionally substituted with substituent B", when the C1 to C6 alkyl group has substituent B, the hydrogen atom in the C1 to C6 alkyl group is optionally substituted by 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 amino group, methylamino group, It is an ethylamino group, a dimethylamino group, an ethylmethylamino group, or a diethylamino group.
For example, in preferred embodiments, R1 represents a methyl group, an ethyl group, or a 2,2-difluoroethyl group.

R2 in formula (1) is a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1 to C6 alkyl group which may be optionally substituted with substituent C, a C1 to C6 haloalkyl group, or a C1 to C6 haloalkyl group, which is optionally substituted with substituent C. a C3-C8 cycloalkyl group which may be optionally substituted with a substituent C, a C2-C6 alkenyl group which may be optionally substituted with a substituent C, a C2-C6 haloalkenyl group which may be optionally substituted with a substituent C; Alkynyl group, C2-C6 haloalkynyl group, C1-C6 alkoxy group optionally substituted with substituent C, C1-C6 haloalkoxy group, C3-C8 haloalkoxy group optionally substituted with substituent C Cycloalkoxy group, C2-C6 alkenyloxy group optionally substituted with substituent C, C2-C6 haloalkenyloxy group, C3-C6 alkynyloxy group optionally substituted with substituent C, C3 -C6 haloalkynyloxy group, RdC(=O)- (wherein, Rd is a hydrogen atom, a C1-C6 alkyl group which may be optionally substituted with substituent B, a C1-C6 haloalkyl group, 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- (where Ra and Rb have the same meanings as above). ), RdC(=O)O- (here, Rd has the same meaning as above), Rc-L- (here, Rc is a C1-C6 alkyl group or a C1-C6 haloalkyl group) (wherein, L represents S, SO, or SO ₂ ), RaRbN- (where Ra and Rb have the same meanings as above), or ReC(=O)N(Rf)- (wherein , Re is a hydrogen atom, a C1 to C6 alkyl group which may be appropriately substituted with substituent B, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group, a C1 to C6 alkoxy group, a C1 to C6 alkyl group, Represents a haloalkoxy group, a C3 to C8 cycloalkoxy group, or RaRbN- (where Ra and Rb have the same meanings as above), and Rf may be optionally substituted with a hydrogen atom or substituent B. represents a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group.

Among these, R2 is a halogen atom, a hydroxyl group, a cyano group, a C1 to C6 alkyl group optionally substituted with substituent C, a C1 to C6 haloalkyl group, and a C2 to C6 alkyl group optionally substituted with substituent C. Alkenyl group, C2-C6 alkynyl group optionally substituted with substituent C, C1-C6 alkoxy group optionally substituted with substituent C, C1-C6 haloalkoxy group, optionally substituted with substituent C An optionally substituted C2-C6 alkenyloxy group, a C3-C6 alkynyloxy group optionally substituted with substituent C, or Rc-L- (where Rc and L are as defined above) ) is preferred;
In particular, R2 is a halogen atom, a C1 to C6 alkyl group optionally substituted with a substituent C, a C1 to C6 alkoxy group optionally substituted with a substituent C, or Rc-L- (wherein Rc and L have the same meanings as above.) is preferable,
Further, R2 is preferably a halogen atom or a C1 to C6 alkyl group which may be optionally substituted with a substituent C,
More preferably, R2 is a halogen atom.

The halogen atom for R2 in formula (1) has the same meaning as defined above, and is preferably a fluorine atom, chlorine atom, bromine atom, or iodine atom.

R2 in formula (1) includes a hydroxyl group, a cyano group, and a nitro group.

The C1 to C6 alkyl group of the "C1 to C6 alkyl group optionally substituted with substituent C" in R2 of formula (1) has the same meaning as the above definition, and is preferably a methyl group or an ethyl group. , a propyl group, or an isopropyl group, and more preferably a methyl group or an ethyl group. When the substituent C is present, a hydrogen atom in the C1 to C6 alkyl group is optionally substituted with the substituent C.

The "C1 to C6 haloalkyl group" in R2 of formula (1) has the same meaning as the above definition, and is preferably a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, or a 2,2, A 2-trifluoroethyl group, more preferably a difluoromethyl group or a trifluoromethyl group.

The C3 to C8 cycloalkyl group of the "C3 to C8 cycloalkyl group optionally substituted with substituent C" in R2 of formula (1) has the same meaning as the above definition, and is preferably a cyclopropyl group. , a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, and more preferably a cyclopropyl group or a cyclobutyl group. When the substituent C is present, a hydrogen atom in the C3 to C8 cycloalkyl group is optionally substituted with the substituent C.

The C2 to C6 alkenyl group of the "C2 to C6 alkenyl group optionally substituted with substituent C" in R2 of formula (1) has the same meaning as the above definition, and is preferably a vinyl group, 1- It is a propenyl group or an allyl group, and more preferably a vinyl group. When a substituent C is present, a hydrogen atom in a C2 to C6 alkenyl group is optionally substituted with the substituent C.

The "C2 to C6 haloalkenyl group" in R2 of formula (1) has the same meaning as the above definition, 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, and more preferably 2-fluorovinyl group or 2,2-difluorovinyl group.

The C2 to C6 alkynyl group of the "C2 to C6 alkynyl group optionally substituted with substituent C" in R2 of formula (1) has the same meaning as the above definition, and is preferably an ethynyl group, 1- A propynyl group or a propargyl group, more preferably an ethynyl group. When the substituent C is present, a hydrogen atom in the C2 to C6 alkynyl group is optionally substituted with the substituent C.

The "C2 to C6 haloalkynyl group" in R2 of formula (1) has the same meaning as the above definition, and is preferably a 3,3-difluoro-1-propynyl group, a 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- A 2-butynyl group, more preferably a 3,3-difluoro-1-propynyl group or a 3,3,3-trifluoro-1-propynyl group.

The C1 to C6 alkoxy group of the "C1 to C6 alkoxy group optionally substituted with substituent C" in R2 of formula (1) has the same meaning as the above definition, and is preferably a methoxy group or an ethoxy group. , a propyloxy group, or an isopropyloxy group, and more preferably a methoxy group or an ethoxy group. When the substituent C is present, a hydrogen atom in the C1 to C6 alkoxy group is optionally substituted with the substituent C.

The "C1 to C6 haloalkoxy group" in R2 of formula (1) has the same meaning as the above definition, and is preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2, A 2-trifluoroethoxy group, a 3,3-difluoropropyloxy group, or a 3,3,3-trifluoropropyloxy group, more preferably a difluoromethoxy group or a trifluoromethoxy group.

The C3 to C8 cycloalkoxy group of the "C3 to C8 cycloalkoxy group optionally substituted with substituent C" in R2 of formula (1) has the same meaning as the above definition, and is preferably cyclopropyloxy. group, cyclobutoxy group, cyclopentyloxy group, or cyclohexyloxy group, and more preferably cyclopropyloxy group or cyclobutoxy group. When the substituent C is present, a hydrogen atom in the C3 to C8 cycloalkoxy group is optionally substituted with the substituent C.

The C2 to C6 alkenyloxy group of the "C2 to C6 alkenyloxy group optionally substituted with substituent C" in R2 of formula (1) has the same meaning as the above definition, and is preferably a vinyloxy group, A 1-propenyloxy group or an allyloxy group, more preferably a vinyloxy group. When the substituent C is present, a hydrogen atom in the C2 to C6 alkenyloxy group is optionally substituted with the substituent C.

The "C2 to C6 haloalkenyloxy group" in R2 of formula (1) has the same meaning as the above definition, and is 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-difluoroallyloxy group. It is a vinyloxy group.

The C3 to C6 alkynyloxy group of the "C3 to C6 alkynyloxy group optionally substituted with substituent C" in R2 of formula (1) has the same meaning as the above definition, and is preferably a propargyloxy group. , 2-butynyloxy group, or 3-butynyloxy group, and more preferably propargyloxy group or 2-butynyloxy group. When the substituent C is present, a hydrogen atom in the C3 to C6 alkynyloxy group is optionally substituted with the substituent C.

The "C3 to C6 haloalkynyloxy group" in R2 of formula (1) has the same meaning as the above definition, and is preferably a 4,4-difluoro-2-butynyloxy group, a 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- It is a butynyloxy group or a 4,4,4-trifluoro-2-butynyloxy group.

"RdC(=O)-" in R2 of formula (1) (here, Rd is a hydrogen atom, a C1 to C6 alkyl group that may be appropriately substituted with substituent B, a C1 to 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 have the same meanings as above). each term (represented) has the same meaning as defined above. Regarding the "C1 to C6 alkyl group which may be optionally substituted with substituent B", when the C1 to C6 alkyl group has substituent B, the hydrogen atom in the C1 to C6 alkyl group is optionally substituted by substituent B. . "RdC(=O)-" is preferably a formyl group, an acetyl group, a methoxyacetyl group, a cyanoacetyl group, a propionyl group, a difluoroacetyl group, a trifluoroacetyl group, a cyclopropanecarbonyl group, a methoxycarbonyl group, or an ethoxycarbonyl group. 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-difluoroethylamino carbonyl group, 2,2,2-trifluoroethylaminocarbonyl group, cyclopropylaminocarbonyl group, (cyclopropyl)methylaminocarbonyl group, pyrrolidinylcarbonyl group, or piperidinylcarbonyl group, more preferably, An acetyl group, a methoxyacetyl group, a cyanoacetyl group, a propionyl group, a methoxycarbonyl group, or an ethoxycarbonyl group.

Rd of "RdC(=O)O-" in R2 of formula (1) has the same meaning as the above definition. "RdC(=O)O-" is preferably a formyloxy group, an acetyloxy group, a methoxyacetyloxy group, a cyanoacetyloxy group, a propionyloxy group, a difluoroacetyloxy group, a trifluoroacetyloxy group, or a cyclopropanecarbonyl group. Oxy group, methoxycarbonyloxy group, ethoxycarbonyloxy group, 2,2-difluoroethoxycarbonyloxy group, 2,2,2-trifluoroethoxycarbonyloxy group, 3,3,3-trifluoropropyloxycarbonyloxy group, Cyclopropyloxycarbonyloxy group, aminocarbonyloxy group, methylaminocarbonyloxy group, ethylaminocarbonyloxy group, (methoxymethyl)aminocarbonyloxy group, (2-methoxyethyl)aminocarbonyloxy group, (cyanomethyl)aminocarbonyloxy group 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, cyclopropylamino carbonyloxy group, (cyclopropyl)methylaminocarbonyloxy group, pyrrolidinylcarbonyloxy group, or piperidinylcarbonyloxy group, more preferably acetyloxy group, methoxyacetyloxy group, cyanoacetyloxy group, or It is a propionyloxy group.

"Rc-L-" in R2 of formula (1) (here, Rc represents a C1 to C6 alkyl group or a C1 to C6 haloalkyl group, and L represents S, SO, or SO _2. ) each term has the same meaning as defined above. "Rc-L-" is preferably a methylthio group, methanesulfinyl group, methanesulfonyl group, ethylthio group, ethanesulfinyl group, ethanesulfonyl group, trifluoromethylthio group, trifluoromethanesulfinyl group, or trifluoromethanesulfonyl group. , more preferably a methylthio group, a methanesulfinyl group, or a methanesulfonyl group.

Ra and Rb of "RaRbN-" in R2 of formula (1) have the same meanings as above. "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, piperidinyl group, or morpholyl group, more preferably amino group, methyl An amino group, an ethylamino group, a dimethylamino group, an ethylmethylamino group, a diethylamino group, a pyrrolidinyl group, a piperidinyl group, or a morpholyl group.

"ReC(=O)N(Rf)-" in R2 of formula (1) (where Re is a hydrogen atom, a C1 to C6 alkyl group which may be optionally substituted with a substituent B, a C1 to C6 alkyl group) Haloalkyl group, C3-C8 cycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group, or RaRbN- (where Ra and Rb have the same meanings as above) ), and Rf represents a hydrogen atom, a C1 to C6 alkyl group optionally substituted with substituent B, a C1 to C6 haloalkyl group, or a C3 to C8 cycloalkyl group. Terms have the same meanings as defined above. Regarding the "C1 to C6 alkyl group optionally substituted with substituent B" in Re and Rf, when substituent B is present, the hydrogen atom in the C1 to C6 alkyl group can be optionally substituted by substituent B. will be replaced with Re is preferably a hydrogen atom, methyl group, methoxymethyl group, cyanomethyl group, ethyl group, difluoromethyl group, trifluoromethyl group, cyclopropyl group, methoxy group, 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 methyl group. , or an ethyl group. Rf is preferably a hydrogen atom, methyl group, methoxymethyl group, ethoxymethyl group, cyanomethyl group, ethyl group, 2-methoxyethyl group, 2-ethoxyethyl group, 2-cyanoethyl group, propyl group, 2,2- A difluoroethyl group, a 2,2,2-trifluoroethyl group, or a cyclopropyl group, and more preferably a hydrogen atom, a methyl group, or an ethyl group.

R3 in formula (1) has the same meaning as R2 described above. That is, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1-C6 alkyl group optionally substituted with substituent C, a C1-C6 haloalkyl group, a C3-C8 optionally substituted with substituent C. 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 haloalkynyl group, C1 to C6 alkoxy group optionally substituted with substituent C, C1 to C6 haloalkoxy group, C3 to C8 cycloalkoxy group optionally substituted with substituent C, substituent C2 to C6 alkenyloxy group optionally substituted with C, C2 to C6 haloalkenyloxy group, C3 to C6 alkynyloxy group optionally substituted with substituent C, C3 to C6 haloalkynyloxy group, RdC(=O)-(here, Rd has the same meaning as above), RdC(=O)O-(here, Rd has the same meaning as above), Rc-L-( Here, Rc and L have the same meanings as above.), RaRbN- (where Ra and Rb have the same meanings as above), or ReC(=O)N(Rf)-(here, Re and Rf have the same meanings as above.

Among them, R3 is a halogen atom, a hydroxyl group, a cyano group, a C1 to C6 alkyl group optionally substituted with substituent C, a C1 to C6 haloalkyl group, and a C2 to C6 alkyl group optionally substituted with substituent C. Alkenyl group, C2-C6 alkynyl group optionally substituted with substituent C, C1-C6 alkoxy group optionally substituted with substituent C, C1-C6 haloalkoxy group, optionally substituted with substituent C An optionally substituted C2-C6 alkenyloxy group, a C3-C6 alkynyloxy group optionally substituted with substituent C, or Rc-L- (where Rc and L are as defined above) ) is preferred;
In particular, R3 is a halogen atom, a C1 to C6 alkyl group optionally substituted with a substituent C, a C1 to C6 alkoxy group optionally substituted with a substituent C, or Rc-L- (wherein, Rc and L have the same meanings as above.) is preferred.

The halogen atom for R3 in formula (1) has the same meaning as defined above, and is preferably a fluorine atom, chlorine atom, bromine atom, or iodine atom.

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

The C1 to C6 alkyl group of the "C1 to C6 alkyl group optionally substituted with substituent C" in R3 of formula (1) has the same meaning as the above definition, and is preferably a methyl group or an ethyl group. , propyl group, isopropyl group, butyl group, or isobutyl group, and more preferably methyl group, ethyl group, propyl group, or isopropyl group. When the substituent C is present, a hydrogen atom in the C1 to C6 alkyl group is optionally substituted with the substituent C.

The "C1 to C6 haloalkyl group" in R3 of formula (1) has the same meaning as the above definition, and is preferably a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, or a 2,2, A 2-trifluoroethyl group, more preferably a difluoromethyl group or a trifluoromethyl group.

The C3 to C8 cycloalkyl group of the "C3 to C8 cycloalkyl group optionally substituted with substituent C" in R3 of formula (1) has the same meaning as the above definition, and is preferably a cyclopropyl group. , a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, and more preferably a cyclopropyl group or a cyclobutyl group. When the substituent C is present, a hydrogen atom in the C3 to C8 cycloalkyl group is optionally substituted with the substituent C.

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

The "C2 to C6 haloalkenyl group" in R3 of formula (1) has the same meaning as the above definition, 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, and more preferably 2-fluorovinyl group or 2,2-difluorovinyl group.

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

The "C2 to C6 haloalkynyl group" in R3 of formula (1) has the same meaning as the above definition, and is preferably a 3,3-difluoro-1-propynyl group, a 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- A 2-butynyl group, more preferably a 3,3-difluoro-1-propynyl group or a 3,3,3-trifluoro-1-propynyl group.

The C1 to C6 alkoxy group of the "C1 to C6 alkoxy group optionally substituted with substituent C" in R3 of formula (1) has the same meaning as the above definition, and is preferably a methoxy group or an ethoxy group. , propyloxy group, isopropyloxy group, butoxy group, isobutoxy group, or pentyloxy group, and more preferably methoxy group, ethoxy group, propyloxy group, or isopropyloxy group. When the substituent C is present, a hydrogen atom in the C1 to C6 alkoxy group is optionally substituted with the substituent C.

The "C1 to C6 haloalkoxy group" in R3 of formula (1) has the same meaning as the above definition, and is preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2, 2-trifluoroethoxy group, 3,3-difluoropropyloxy group, or 3,3,3-trifluoropropyloxy group, more preferably difluoromethoxy group, trifluoromethoxy group, 2,2-difluoroethoxy group. or 2,2,2-trifluoroethoxy group.

The C3 to C8 cycloalkoxy group of the "C3 to C8 cycloalkoxy group optionally substituted with substituent C" in R3 of formula (1) has the same meaning as the above definition, and is preferably cyclopropyloxy. group, cyclobutoxy group, cyclopentyloxy group, or cyclohexyloxy group, and more preferably cyclopropyloxy group or cyclobutoxy group. When the substituent C is present, a hydrogen atom in the C3 to C8 cycloalkoxy group is optionally substituted with the substituent C.

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

The "C2-C6 haloalkenyloxy group" in R3 of formula (1) has the same meaning as the above definition, and is 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-difluoroallyloxy group. It is a vinyloxy group.

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

The "C3 to C6 haloalkynyloxy group" in R3 of formula (1) has the same meaning as the above definition, and is preferably a 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- It is a butynyloxy group or a 4,4,4-trifluoro-2-butynyloxy group.

Rd of "RdC(=O)-" in R3 of formula (1) has the same meaning as the above definition. "RdC(=O)-" is preferably a formyl group, an acetyl group, a methoxyacetyl group, a cyanoacetyl group, a propionyl group, a difluoroacetyl group, a trifluoroacetyl group, a cyclopropanecarbonyl group, a methoxycarbonyl group, or an ethoxycarbonyl group. 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-difluoroethylamino carbonyl group, 2,2,2-trifluoroethylaminocarbonyl group, cyclopropylaminocarbonyl group, (cyclopropyl)methylaminocarbonyl group, pyrrolidinylcarbonyl group, or piperidinylcarbonyl group, more preferably, An acetyl group, a methoxyacetyl group, a cyanoacetyl group, a propionyl group, a methoxycarbonyl group, or an ethoxycarbonyl group.

Rd of "RdC(=O)O-" in R3 of formula (1) has the same meaning as the above definition. "RdC(=O)O-" is preferably a formyloxy group, an acetyloxy group, a methoxyacetyloxy group, a cyanoacetyloxy group, a propionyloxy group, a difluoroacetyloxy group, a trifluoroacetyloxy group, or a cyclopropanecarbonyl group. Oxy group, methoxycarbonyloxy group, ethoxycarbonyloxy group, 2,2-difluoroethoxycarbonyloxy group, 2,2,2-trifluoroethoxycarbonyloxy group, 3,3,3-trifluoropropyloxycarbonyloxy group, Cyclopropyloxycarbonyloxy group, aminocarbonyloxy group, methylaminocarbonyloxy group, ethylaminocarbonyloxy group, (methoxymethyl)aminocarbonyloxy group, (2-methoxyethyl)aminocarbonyloxy group, (cyanomethyl)aminocarbonyloxy group 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, cyclopropylamino carbonyloxy group, (cyclopropyl)methylaminocarbonyloxy group, pyrrolidinylcarbonyloxy group, or piperidinylcarbonyloxy group, more preferably acetyloxy group, methoxyacetyloxy group, cyanoacetyloxy group, or It is a propionyloxy group.

Rc and L of "Rc-L-" in R3 of formula (1) are as defined above. Rc is preferably a C1 to C6 alkyl group. "Rc-L-" is preferably a methylthio group, methanesulfinyl group, methanesulfonyl group, ethylthio group, ethanesulfinyl group, ethanesulfonyl group, trifluoromethylthio group, trifluoromethanesulfinyl group, or trifluoromethanesulfonyl group. More preferably, a methylthio group, a methanesulfinyl group, a methanesulfonyl group, an ethylthio group, an ethanesulfinyl group, or an ethanesulfonyl group.

Ra and Rb of "RaRbN-" in R3 of formula (1) have the same meanings as above. "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, piperidinyl group, or morpholyl group, more preferably amino group, methyl An amino group, an ethylamino group, a dimethylamino group, an ethylmethylamino group, a diethylamino group, a pyrrolidinyl group, a piperidinyl group, or a morpholyl group.

Re and Rf of "ReC(=O)N(Rf)-" in R3 of formula (1) have the same meanings as the above definitions. Re is preferably a hydrogen atom, methyl group, methoxymethyl group, cyanomethyl group, ethyl group, difluoromethyl group, trifluoromethyl group, cyclopropyl group, methoxy group, 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 methyl group. , or an ethyl group. Further, Rf 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, and more preferably a hydrogen atom, a methyl group, or an ethyl group.
For example, in a preferred embodiment, R2 and R3 are each independently a halogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, or Rc-L- (where Rc is a C1-C6 represents an alkyl group or a C1 to C6 haloalkyl group, and L represents S, SO, or SO ₂ ).
For example, in a preferred embodiment, R2 and R3 each independently represent a fluorine atom, a chlorine atom, a methyl group, a methoxy group, a methylthio group, a methanesulfinyl group, or a methanesulfonyl group.

n in formula (1) is an integer from 0 to 4. In this case, it is assumed that all integers between 0 and 4 are also individually disclosed. That is, n means 0, 1, 2, 3, or 4. However, when n is 2 or more, 2 or more R3's each represent an independent substituent, and may be the same or different, and can be arbitrarily selected.

R4 in formula (1) is a halogen atom, a cyano group, a nitro group, a C1-C6 alkyl group optionally substituted with substituent A, a C1-C6 haloalkyl group, optionally substituted with substituent A. Good C3-C8 cycloalkyl group, C2-C6 alkenyl group optionally substituted with substituent A, C2-C6 haloalkenyl group, C2-C6 alkynyl group optionally substituted with substituent A. , C2 to C6 haloalkynyl group, C1 to C6 alkoxy group optionally substituted with substituent A, C1 to C6 haloalkoxy group, C3 to C8 cycloalkoxy optionally substituted with substituent A group, a C2-C6 alkenyloxy group optionally substituted with substituent A, a C2-C6 haloalkenyloxy group, a C3-C6 alkynyloxy group optionally substituted with substituent A, C3-C6 haloalkynyloxy group, Rc-L- (here, Rc and L have the same meanings as above), RaRbN- (here, Ra and Rb have the same meanings as above), or RgC (= O)-(Here, Rg is a hydrogen atom, a hydroxyl group, a C1 to C6 alkyl group which may be optionally substituted with substituent B, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group, a C1 to C6 cycloalkyl group, represents an alkoxy group, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group, or RaRbN- (where Ra and Rb have the same meanings as above).

Among them, R4 is a halogen atom, a C1 to C6 alkyl group optionally substituted with a substituent A, a C1 to C6 haloalkyl group, a C2 to C6 alkenyl group optionally substituted with a substituent A, a substituent A C2 to C6 alkynyl group optionally substituted with A, a C1 to C6 alkoxy group optionally substituted with substituent A, or RgC(=O)- (where Rg has the same meaning as above) ) is preferred;
In particular, R4 is preferably a halogen atom.

R4 in formula (1) includes a cyano group and a nitro group.
The halogen atom for R4 in formula (1) has the same meaning as defined above, and is preferably a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, and more preferably a chlorine atom or a bromine atom.

The C1 to C6 alkyl group of the "C1 to C6 alkyl group optionally substituted with substituent A" in R4 of formula (1) has the same meaning as the above definition, and is preferably a methyl group or an ethyl group. , propyl group, isopropyl group, butyl group, or isobutyl group, and more preferably methyl group or ethyl group. When a substituent A is present, a hydrogen atom in a C1 to C6 alkyl group is optionally substituted with the substituent A.

The "C1 to C6 haloalkyl group" in R4 of formula (1) has the same meaning as the above definition, and is preferably a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, a 2,2,2 -trifluoroethyl group, 3,3-difluoropropyl group, or 3,3,3-trifluoropropyl group, and more preferably difluoromethyl group or trifluoromethyl group.

The C3 to C8 cycloalkyl group of the "C3 to C8 cycloalkyl group optionally substituted with substituent A" in R4 of formula (1) has the same meaning as the above definition, and is preferably a cyclopropyl group. , a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, and more preferably a cyclopropyl group or a cyclobutyl group. When a substituent A is present, a hydrogen atom in a C3 to C8 cycloalkyl group is optionally substituted with the substituent A.

The C2 to C6 alkenyl group of the "C2 to C6 alkenyl group optionally substituted with substituent A" in R4 of formula (1) has the same meaning as the above definition, and is preferably a vinyl group, 1- A propenyl group, an allyl group, a 1-butenyl group, a 2-butenyl group, or a 3-butenyl group, and more preferably a vinyl group, a 1-propenyl group, or an allyl group. When a substituent A is present, a hydrogen atom in a C2 to C6 alkenyl group is optionally substituted with the substituent A.

The "C2-C6 haloalkenyl group" in R4 of formula (1) has the same meaning as the above definition, 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, and more preferably 2-fluorovinyl group or 2,2-difluorovinyl group.

The C2 to C6 alkynyl group of the "C2 to C6 alkynyl group optionally substituted with substituent A" in R4 of formula (1) has the same meaning as the above definition, and is preferably an ethynyl group, 1- A propynyl group, a propargyl group, a 1-butynyl group, a 2-butynyl group, or a 3-butynyl group, and more preferably an ethynyl group, a 1-propynyl group, or a propargyl group. When a substituent A is present, a hydrogen atom in a C2 to C6 alkynyl group is optionally substituted with the substituent A.

The "C2 to C6 haloalkynyl group" in R4 of formula (1) has the same meaning as the above definition, and is preferably a 3,3-difluoro-1-propynyl group, a 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- A 2-butynyl group, more preferably a 3,3-difluoro-1-propynyl group or a 3,3,3-trifluoro-1-propynyl group.

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

The "C1 to C6 haloalkoxy group" in R4 of formula (1) has the same meaning as the above definition, and is preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2, 2-trifluoroethoxy group, 3,3-difluoropropyloxy group, or 3,3,3-trifluoropropyloxy group, more preferably difluoromethoxy group, trifluoromethoxy group, 2,2-difluoroethoxy group. or 2,2,2-trifluoroethoxy group.

The C3 to C8 cycloalkoxy group of the "C3 to C8 cycloalkoxy group optionally substituted with substituent A" in R4 of formula (1) has the same meaning as the above definition, and is preferably cyclopropyloxy. group, cyclobutoxy group, cyclopentyloxy group, or cyclohexyloxy group, and more preferably cyclopropyloxy group or cyclobutoxy group. When a substituent A is present, a hydrogen atom in a C3 to C8 cycloalkoxy group is optionally substituted with the substituent A.

The C2 to C6 alkenyloxy group of the "C2 to C6 alkenyloxy group optionally substituted with substituent A" in R4 of formula (1) has the same meaning as the above definition, and is preferably a vinyloxy group, A 1-propenyloxy group, an allyloxy group, a 1-butenyloxy group, a 2-butenyloxy group, or a 3-butenyloxy group, and more preferably a vinyloxy group, a 1-propenyloxy group, or an allyloxy group. When a substituent A is present, a hydrogen atom in a C2 to C6 alkenyloxy group is optionally substituted with the substituent A.

"C2-C6 haloalkenyloxy group" in R4 of formula (1) has the same meaning as the above definition, and includes 2-fluorovinyloxy group, 2,2-difluorovinyloxy group, 2,2-dichlorovinyloxy group, group, 3-fluoroallyloxy group, 3,3-difluoroallyloxy group, or 3,3-dichloroallyloxy group, more preferably 2-fluorovinyloxy group or 2,2-difluorovinyloxy group. It is.

The C3 to C6 alkynyloxy group of the "C3 to C6 alkynyloxy group optionally substituted with substituent A" in R4 of formula (1) has the same meaning as the above definition, and is preferably a propargyloxy group. , 2-butynyloxy group, or 3-butynyloxy group, and more preferably propargyloxy group. When a substituent A is present, a hydrogen atom in a C3 to C6 alkynyloxy group is optionally substituted with the substituent A.

The "C3 to C6 haloalkynyloxy group" in R4 of formula (1) has the same meaning as the above definition, and is preferably a 4,4-difluoro-2-butynyloxy group, a 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- It is a butynyloxy group or a 4,4,4-trifluoro-2-butynyloxy group.

Rc and L of "Rc-L-" in R4 of formula (1) have the same meanings as above. "Rc-L-" is preferably a methylthio group, methanesulfinyl group, methanesulfonyl group, ethylthio group, ethanesulfinyl group, ethanesulfonyl group, trifluoromethylthio group, trifluoromethanesulfinyl group, or trifluoromethanesulfonyl group. , more preferably a methylthio group, a methanesulfinyl group, or a methanesulfonyl group.

Ra and Rb of "RaRbN-" in R4 of formula (1) have the same meanings as above. "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. group, or diethylamino group.

"RgC(=O)-" in R4 of formula (1) (where Rg is a hydrogen atom, a hydroxyl group, a C1 to C6 alkyl group that may be appropriately substituted with substituent B, a C1 to C6 haloalkyl group, C3 to C8 cycloalkyl group, C1 to C6 alkoxy group, C1 to C6 haloalkoxy group, C3 to C8 cycloalkoxy group, or RaRbN- (where Ra and Rb are as defined above). ) has the same meaning as defined above. Regarding the "C1 to C6 alkyl group which may be optionally substituted with substituent B", when the C1 to C6 alkyl group has substituent B, the hydrogen atom in the C1 to C6 alkyl group is optionally substituted by substituent B. . "RgC(=O)-" is preferably a formyl group, a hydroxycarbonyl group, an acetyl group, a methoxyacetyl group, a cyanoacetyl group, a propionyl group, a difluoroacetyl group, a trifluoroacetyl group, a cyclopropanecarbonyl group, or a methoxycarbonyl group. 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, ethyl Methylaminocarbonyl 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, or piperidinylcarbonyl group, More preferred are an acetyl group, a methoxyacetyl group, a cyanoacetyl group, or a propionyl group.

R5 in formula (1) is a halogen atom, a cyano group, a nitro group, a C1 to C6 alkyl group optionally substituted with substituent C, a C1 to C6 haloalkyl group, optionally substituted with substituent C Good 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 to C6 haloalkynyl group, C1 to C6 alkoxy group optionally substituted with substituent C, C1 to C6 haloalkoxy group, C3 to C8 cycloalkoxy optionally substituted with substituent C group, a C2-C6 alkenyloxy group optionally substituted with substituent C, a C2-C6 haloalkenyloxy group, a C3-C6 alkynyloxy group optionally substituted with substituent C, C3-C6 haloalkynyloxy group, RdC(=O)-(herein, Rd has the same meaning as above), RdC(=O)O-(herein, Rd has the same meaning as above), Rc -L- (here, Rc and L have the same meanings as above), RaRbN- (here, Ra and Rb have the same meanings as above), ReC(=O)N(Rf)-( Here, Re and Rf have the same meanings as above.), RhON=C(Ri)- (Here, Rh and Ri each independently represent a hydrogen atom or a C1 to C6 alkyl group. ), or a phenyl group which may be optionally substituted with 0 to 5 substituents D (however, in the case of two or more substituents D, each is independent).

Among them, R5 is a halogen atom, a cyano group, a C1 to C6 alkyl group optionally substituted with substituent C, a C1 to C6 haloalkyl group, and a C3 to C8 cycloalkyl group optionally substituted with substituent C. C2-C6 alkenyl group optionally substituted with substituent C, C2-C6 haloalkenyl group, C2-C6 alkynyl group optionally substituted with substituent C, C2-C6 haloalkynyl group, a C1 to C6 alkoxy group which may be optionally substituted with substituent C, a C2 to C6 alkenyloxy group which may be optionally substituted with substituent C, C3 to C6 which may be optionally substituted with substituent C an alkynyloxy group, RdC(=O)- (here, Rd has the same meaning as above), Rc-L- (here, Rc and L have the same meaning as above), RaRbN-( Here, Ra and Rb have the same meanings as above.), RhON=C(Ri)- (Here, Rh and Ri have the same meanings as above.), or 0 to 5 substitutions as appropriate with substituent D. A phenyl group that may be substituted (however, in the case of two or more substituents D, each is independent) is preferable,
In particular, R5 is a halogen atom, a cyano group, a C1-C6 alkyl group optionally substituted with substituent C, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group optionally substituted with substituent C. group, a C2-C6 alkenyl group optionally substituted with substituent C, a C2-C6 alkynyl group optionally substituted with substituent C, a C1-C6 alkenyl group optionally substituted with substituent C Alkoxy group, RdC(=O)- (here, Rd has the same meaning as above), Rc-L- (here, Rc and L have the same meaning as above), RhON=C(Ri )-(Here, Rh and Ri have the same meanings as above.), or a phenyl group that may be optionally substituted with 0 to 5 substituents D (however, in the case of two or more substituents D, each independently ) is preferred.
For example, in a preferred embodiment, R5 is a halogen atom, a cyano group, a C1 to C6 alkyl group optionally substituted with substituent C, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group, a C2 to C6 alkenyl group, C2 to C6 alkynyl group, C1 to C6 alkoxy group, RdC(=O)- (here, Rd has the same meaning as above), Rc-L- (here, Rc and L has the same meaning as above), RhON=C(Ri)- (where Rh and Ri have the same meaning as above), or a phenyl group.

The halogen atom in R5 in formula (1) has the same meaning as defined above, and is preferably a fluorine atom, chlorine atom, bromine atom, or iodine atom.

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

The C1 to C6 alkyl group of the "C1 to C6 alkyl group optionally substituted with substituent C" in R5 of formula (1) has the same meaning as the above definition, and is preferably a methyl group or an ethyl group. , propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, t-butyl group, or pentyl group, more preferably methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group. , sec-butyl group, or t-butyl group. When the substituent C is present, a hydrogen atom in the C1 to C6 alkyl group is optionally substituted with the substituent C.

"C1-C6 haloalkyl group" in R5 of formula (1) has the same meaning as the above definition, and is preferably a difluoromethyl group, dibromomethyl group, trifluoromethyl group, trichloromethyl group, 2,2-difluoromethyl group, Ethyl group, 2,2,2-trifluoroethyl group, 3,3-difluoropropyl group, or 3,3,3-trifluoropropyl group, more preferably difluoromethyl group or trifluoromethyl group. .

The C3 to C8 cycloalkyl group of the "C3 to C8 cycloalkyl group optionally substituted with substituent C" in R5 of formula (1) has the same meaning as the above definition, and is preferably a cyclopropyl group. , a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, and more preferably a cyclopropyl group or a cyclobutyl group. When the substituent C is present, a hydrogen atom in the C3 to C8 cycloalkyl group is optionally substituted with the substituent C.

The C2 to C6 alkenyl group of the "C2 to C6 alkenyl group optionally substituted with substituent C" in R5 of formula (1) has the same meaning as the above definition, and is preferably a vinyl group, 1- Propenyl group, allyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, or 2-methyl-1-propenyl group, more preferably vinyl group, 1-propenyl group, allyl group, or 2-methyl-1-propenyl group. When a substituent C is present, a hydrogen atom in a C2 to C6 alkenyl group is optionally substituted with the substituent C.

The "C2-C6 haloalkenyl group" in R5 of formula (1) has the same meaning as the above definition, 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, and more preferably 2-fluorovinyl group or 2,2-difluorovinyl group.

The C2 to C6 alkynyl group of the "C2 to C6 alkynyl group optionally substituted with substituent C" in R5 of formula (1) has the same meaning as the above definition, and is preferably an ethynyl group, 1- A propynyl group, a propargyl group, a 1-butynyl group, a 2-butynyl group, or a 3-butynyl group, and more preferably an ethynyl group, a 1-propynyl group, or a propargyl group. When the substituent C is present, a hydrogen atom in the C2 to C6 alkynyl group is optionally substituted with the substituent C.

The "C2-C6 haloalkynyl group" in R5 of formula (1) has the same meaning as the above definition, and is preferably a 3,3-difluoro-1-propynyl group, a 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- A 2-butynyl group, more preferably a 3,3-difluoro-1-propynyl group or a 3,3,3-trifluoro-1-propynyl group.

The C1 to C6 alkoxy group of the "C1 to C6 alkoxy group optionally substituted with substituent C" in R5 of formula (1) has the same meaning as the above definition, and is preferably a methoxy group or an ethoxy group. , a propyloxy group, or an isopropyloxy group, and more preferably a methoxy group or an ethoxy group. When the substituent C is present, a hydrogen atom in the C1 to C6 alkoxy group is optionally substituted with the substituent C.

The "C1 to C6 haloalkoxy group" in R5 of formula (1) has the same meaning as the above definition, and is preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2, 2-trifluoroethoxy group, 3,3-difluoropropyloxy group, or 3,3,3-trifluoropropyloxy group, more preferably difluoromethoxy group, trifluoromethoxy group, 2,2-difluoroethoxy group. or 2,2,2-trifluoroethoxy group.

The C3 to C8 cycloalkoxy group of the "C3 to C8 cycloalkoxy group optionally substituted with substituent C" in R5 of formula (1) has the same meaning as the above definition, and is preferably cyclopropyloxy. group, cyclobutoxy group, cyclopentyloxy group, or cyclohexyloxy group, and more preferably cyclopropyloxy group or cyclobutoxy group. When the substituent C is present, a hydrogen atom in the C3 to C8 cycloalkoxy group is optionally substituted with the substituent C.

The C2 to C6 alkenyloxy group of the "C2 to C6 alkenyloxy group optionally substituted with substituent C" in R5 of formula (1) has the same meaning as the above definition, and is preferably a vinyloxy group, A 1-propenyloxy group or an allyloxy group, more preferably a vinyloxy group. When the substituent C is present, a hydrogen atom in the C2 to C6 alkenyloxy group is optionally substituted with the substituent C.

"C2-C6 haloalkenyloxy group" in R5 of formula (1) has the same meaning as the above definition, and includes 2-fluorovinyloxy group, 2,2-difluorovinyloxy group, 2,2-dichlorovinyloxy group group, 3-fluoroallyloxy group, 3,3-difluoroallyloxy group, or 3,3-dichloroallyloxy group, more preferably 2-fluorovinyloxy group or 2,2-difluorovinyloxy group. It is.

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

The "C3 to C6 haloalkynyloxy group" in R5 of formula (1) has the same meaning as the above definition, and is preferably a 4,4-difluoro-2-butynyloxy group, a 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- It is a butynyloxy group or a 4,4,4-trifluoro-2-butynyloxy group.

Rd of "RdC(=O)-" in R5 of formula (1) has the same meaning as the above definition. Rd is preferably a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent B, a C1-C6 haloalkyl group, or a C1-C6 alkoxy group, more preferably a hydrogen atom, or a C1 to C6 alkoxy group. "RdC(=O)-" is preferably a formyl group, an acetyl group, a methoxyacetyl group, a cyanoacetyl group, a propionyl group, a difluoroacetyl group, a trifluoroacetyl group, a cyclopropanecarbonyl group, a methoxycarbonyl group, or an ethoxycarbonyl group. 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-difluoroethylamino carbonyl group, 2,2,2-trifluoroethylaminocarbonyl group, cyclopropylaminocarbonyl group, (cyclopropyl)methylaminocarbonyl group, pyrrolidinylcarbonyl group, or piperidinylcarbonyl group, more preferably, A formyl group, a methoxycarbonyl group, or an ethoxycarbonyl group.

Rd of "RdC(=O)O-" in R5 of formula (1) has the same meaning as the above definition. "RdC(=O)O-" is preferably a formyloxy group, an acetyloxy group, a methoxyacetyloxy group, a cyanoacetyloxy group, a propionyloxy group, a difluoroacetyloxy group, a trifluoroacetyloxy group, or a cyclopropanecarbonyl group. Oxy group, methoxycarbonyloxy group, ethoxycarbonyloxy group, 2,2-difluoroethoxycarbonyloxy group, 2,2,2-trifluoroethoxycarbonyloxy group, 3,3,3-trifluoropropyloxycarbonyloxy group, Cyclopropyloxycarbonyloxy group, aminocarbonyloxy group, methylaminocarbonyloxy group, ethylaminocarbonyloxy group, (methoxymethyl)aminocarbonyloxy group, (2-methoxyethyl)aminocarbonyloxy group, (cyanomethyl)aminocarbonyloxy group 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, cyclopropylamino Carbonyloxy group, (cyclopropyl)methylaminocarbonyloxy group, pyrrolidinylcarbonyloxy group, or piperidinylcarbonyloxy group, more preferably acetyloxy group, methoxyacetyloxy group, cyanoacetyloxy group, propionyl group. It is an oxy group, a methoxycarbonyloxy group, or an ethoxycarbonyloxy group.

Rc and L of "Rc-L-" in R5 of formula (1) have the same meanings as above. Rc is preferably an alkyl group. "Rc-L-" is preferably a methylthio group, methanesulfinyl group, methanesulfonyl group, ethylthio group, ethanesulfinyl group, ethanesulfonyl group, trifluoromethylthio group, trifluoromethanesulfinyl group, or trifluoromethanesulfonyl group. , more preferably a methylthio group, a methanesulfinyl group, or a methanesulfonyl group.

Ra and Rb of "RaRbN-" in R5 of formula (1) have the same meanings as above. "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 amino group, dimethylamino group, It is an ethylmethylamino group or a diethylamino group.

Re and Rf of "ReC(=O)N(Rf)-" in R5 of formula (1) have the same meanings as above. Re is preferably a hydrogen atom, methyl group, methoxymethyl group, cyanomethyl group, ethyl group, difluoromethyl group, trifluoromethyl group, cyclopropyl group, methoxy group, 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 methyl group. , or an ethyl group. Rf is preferably a hydrogen atom, methyl group, methoxymethyl group, ethoxymethyl group, cyanomethyl group, ethyl group, 2-methoxyethyl group, 2-ethoxyethyl group, 2-cyanoethyl group, propyl group, 2,2- A difluoroethyl group, a 2,2,2-trifluoroethyl group, or a cyclopropyl group, and more preferably a hydrogen atom, a methyl group, or an ethyl group.

Each term "RhON=C(Ri)-" (wherein Rh and Ri each independently represent a hydrogen atom or a C1 to C6 alkyl group) in R5 of formula (1) is the above-mentioned It is synonymous with the definition of Rh is preferably a hydrogen atom, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, or a t-butyl group, and more preferably a methyl group or an ethyl group. It is. Ri is preferably a hydrogen atom, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, or a t-butyl group, and more preferably a hydrogen atom, a methyl group, It is an ethyl group or a propyl group.

The phenyl group of "the phenyl group which may be optionally substituted with 0 to 5 substituents D" (however, in the case of two or more substituents D, each is independent) in R5 of formula (1) is a substituted When having group D, a hydrogen atom in the phenyl group is optionally substituted with substituent D.
For example, in a preferred embodiment, R5 is a chlorine atom, a bromine atom, an iodine atom, a cyano group, a methyl group, an ethyl group, a propyl group, an isopropyl group, an isobutyl group, a t-butyl group, a 1-hydroxyethyl group, a trifluoro Represents a methyl group, cyclopropyl group, vinyl group, 2-methylpropen-1-yl group, ethynyl group, methoxy group, formyl group, ethoxycarbonyl group, methylthio group, (methoxyimino)methyl group, or phenyl group.

は、２－フルオロフェニル基、２－クロロフェニル基、２－クロロ－４－フルオロフェニル基、２－クロロ－６－フルオロフェニル基、２，４－ジフルオロフェニル基、２，６－ジフルオロフェニル基、２，４，６－トリフルオロフェニル基、２－フルオロ－４－メチルフェニル基、２－フルオロ－４－メトキシフェニル基、２－フルオロ－４－（メチルチオ）フェニル基、２－フルオロ－４－（メタンスルフィニル）フェニル基、または２－フルオロ－４－（メタンスルホニル）フェニル基である。
例えば、好ましい実施態様において、式（１）における部分構造のＡｚ

は、５－クロロ－１H－ピラゾール－１－イル、５－ブロモ－１H－ピラゾール－１－イル、５－ヨード－１H－ピラゾール－１－イル、５－シアノ－１H－ピラゾール－１－イル、３－メチル－１H－ピラゾール－１－イル、５－メチル－１H－ピラゾール－１－イル、５－エチル－１H－ピラゾール－１－イル、５－プロピル－１H－ピラゾール－１－イル、５－イソプロピル－１H－ピラゾール－１－イル、５－イソブチル－１H－ピラゾール－１－イル、５－（t-ブチル）－１H－ピラゾール－１－イル、５－（１－ヒドロキシエチル）－１H－ピラゾール－１－イル、３，５－ジメチル－１H－ピラゾール－１－イル、５－エチル－3-メチル－１H－ピラゾール－１－イル、５－イソプロピル－3-メチル－１H－ピラゾール－１－イル、５－(t-ブチル)－3-メチル－１H－ピラゾール－１－イル、３，５－ジエチル－１H－ピラゾール－１－イル、５－(t-ブチル)－3-エチル－１H－ピラゾール－１－イル、５－クロロ－３－メチル－１H－ピラゾール－１－イル、５－ブロモ－３－メチル－１H－ピラゾール－１－イル、５－（トリフルオロメチル）－１H－ピラゾール－１－イル、３，５－ジ（トリフルオロメチル）－１H－ピラゾール－１－イル、３－メチル－５－（トリフルオロメチル）－１H－ピラゾール－１－イル、５－シクロプロピル－１H－ピラゾール－１－イル、５－シクロプロピル－3－メチル－１H－ピラゾール－１－イル、５－ビニル－１H－ピラゾール－１－イル、５－（２－メチルプロペン－１－イル）－１H－ピラゾール－１－イル、５－エチニル－１H－ピラゾール－１－イル、５－メトキシ－１H－ピラゾール－１－イル、５－ホルミル－１H－ピラゾール－１－イル、３－エトキシカルボニル－５－メチル－１H－ピラゾール－１－イル、５－エトキシカルボニル－３－メチル－１H－ピラゾール－１－イル、５－（メチルチオ）－１H－ピラゾール－１－イル、５－（（メトキシイミノ）メチル）－１H－ピラゾール－１－イル、５－フェニル－１H－ピラゾール－１－イル、または３－メチル－５－フェニル－１H－ピラゾール－１－イルである。m in formula (1) is an integer of 1 to 2. However, when m is 2, each of the two substituents R5 represents an independent substituent, which may be the same or different, and can be arbitrarily selected.
For example, in a preferred embodiment, Ph of the partial structure in formula (1)

is 2-fluorophenyl group, 2-chlorophenyl group, 2-chloro-4-fluorophenyl group, 2-chloro-6-fluorophenyl group, 2,4-difluorophenyl group, 2,6-difluorophenyl group, 2 , 4,6-trifluorophenyl group, 2-fluoro-4-methylphenyl group, 2-fluoro-4-methoxyphenyl group, 2-fluoro-4-(methylthio)phenyl group, 2-fluoro-4-(methane sulfinyl) phenyl group or 2-fluoro-4-(methanesulfonyl) phenyl group.
For example, in a preferred embodiment, the partial structure Az in formula (1)

is 5-chloro-1H-pyrazol-1-yl, 5-bromo-1H-pyrazol-1-yl, 5-iodo-1H-pyrazol-1-yl, 5-cyano-1H-pyrazol-1-yl, 3-Methyl-1H-pyrazol-1-yl, 5-methyl-1H-pyrazol-1-yl, 5-ethyl-1H-pyrazol-1-yl, 5-propyl-1H-pyrazol-1-yl, 5- Isopropyl-1H-pyrazol-1-yl, 5-isobutyl-1H-pyrazol-1-yl, 5-(t-butyl)-1H-pyrazol-1-yl, 5-(1-hydroxyethyl)-1H-pyrazole -1-yl, 3,5-dimethyl-1H-pyrazol-1-yl, 5-ethyl-3-methyl-1H-pyrazol-1-yl, 5-isopropyl-3-methyl-1H-pyrazol-1-yl , 5-(t-butyl)-3-methyl-1H-pyrazol-1-yl, 3,5-diethyl-1H-pyrazol-1-yl, 5-(t-butyl)-3-ethyl-1H-pyrazole -1-yl, 5-chloro-3-methyl-1H-pyrazol-1-yl, 5-bromo-3-methyl-1H-pyrazol-1-yl, 5-(trifluoromethyl)-1H-pyrazol-1 -yl, 3,5-di(trifluoromethyl)-1H-pyrazol-1-yl, 3-methyl-5-(trifluoromethyl)-1H-pyrazol-1-yl, 5-cyclopropyl-1H-pyrazole -1-yl, 5-cyclopropyl-3-methyl-1H-pyrazol-1-yl, 5-vinyl-1H-pyrazol-1-yl, 5-(2-methylpropen-1-yl)-1H-pyrazole -1-yl, 5-ethynyl-1H-pyrazol-1-yl, 5-methoxy-1H-pyrazol-1-yl, 5-formyl-1H-pyrazol-1-yl, 3-ethoxycarbonyl-5-methyl- 1H-pyrazol-1-yl, 5-ethoxycarbonyl-3-methyl-1H-pyrazol-1-yl, 5-(methylthio)-1H-pyrazol-1-yl, 5-((methoxyimino)methyl)-1H -pyrazol-1-yl, 5-phenyl-1H-pyrazol-1-yl, or 3-methyl-5-phenyl-1H-pyrazol-1-yl.

（式中、Ｒ１、Ｒ２、Ｒ３、Ｒ４、ｎ、Ｘおよび破線部は、式（１）と同義である。）、
または式（１－２）

（式中、Ｒ１、Ｒ２、Ｒ３、Ｒ４、ｎ、Ｘおよび破線部は、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 m in formula (1) is 1, formula (1-1)

(In the formula, R1, R2, R3, R4, n, X and the broken line part have the same meaning as in formula (1).)
or formula (1-2)

(In the formula, R1, R2, R3, R4, n, X and the broken line part have the same meanings as in formula (1).) or a salt thereof.

（式中、Ｒ１、Ｒ２、Ｒ３、Ｒ４、ｎ、Ｘおよび破線部は、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 m in formula (1) is 2, formula (1-3)

(In the formula, R1, R2, R3, R4, n, X and the broken line part have the same meanings as in formula (1).) or a salt thereof.

R5a in formula (1-1) and formula (1-3) has the same meaning as R5 described above. That is, a halogen atom, a cyano group, a nitro group, a C1 to C6 alkyl group optionally substituted with a substituent C, a C1 to C6 haloalkyl group, a C3 to C8 cyclo group optionally substituted with a substituent C. Alkyl 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 halo Alkynyl 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 A C2 to C6 alkenyloxy group which may be optionally substituted, a C2 to C6 haloalkenyloxy group, a C3 to C6 alkynyloxy group which may be optionally substituted with substituent C, a C3 to C6 haloalkynyloxy group, RdC(=O)-(here, Rd has the same meaning as above), RdC(=O)O-(here, Rd has the same meaning as above), Rc-L-(here, Rd has the same meaning as above), , Rc and L have the same meanings as above), RaRbN- (where Ra and Rb have the same meanings as above), ReC(=O)N(Rf)- (where Re and Rf has the same meaning as above), RhON=C(Ri)- (where Rh and Ri have the same meaning as above), or a phenyl group which may be optionally substituted with 0 to 5 substituents D. (However, in the case of two or more substituents D, each is independent.)

Among them, R5a is a halogen atom, a cyano group, a C1 to C6 alkyl group optionally substituted with substituent C, a C1 to C6 haloalkyl group, and a C3 to C8 cycloalkyl group optionally substituted with substituent C. C2-C6 alkenyl group optionally substituted with substituent C, C2-C6 haloalkenyl group, C2-C6 alkynyl group optionally substituted with substituent C, C2-C6 haloalkynyl group, a C1 to C6 alkoxy group which may be optionally substituted with substituent C, a C2 to C6 alkenyloxy group which may be optionally substituted with substituent C, C3 to C6 which may be optionally substituted with substituent C an alkynyloxy group, RdC(=O)- (here, Rd has the same meaning as above), Rc-L- (here, Rc and L have the same meaning as above), RaRbN-( Here, Ra and Rb have the same meanings as above.), RhON=C(Ri)- (Here, Rh and Ri have the same meanings as above.), or 0 to 5 substitutions as appropriate with substituent D. A phenyl group that may be substituted (however, in the case of two or more substituents D, each is independent) is preferable,
In particular, R5a is a halogen atom, a cyano group, a C1-C6 alkyl group optionally substituted with substituent C, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group optionally substituted with substituent C. group, a C2-C6 alkenyl group optionally substituted with substituent C, a C2-C6 alkynyl group optionally substituted with substituent C, a C1-C6 alkenyl group optionally substituted with substituent C Alkoxy group, RdC(=O)- (here, Rd has the same meaning as above), Rc-L- (here, Rc and L have the same meaning as above), RhON=C(Ri )-(Here, Rh and Ri have the same meanings as above.), or a phenyl group that may be optionally substituted with 0 to 5 substituents D (however, in the case of two or more substituents D, each independently ) is preferred;
Further, R5a is a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, which may be optionally substituted with a substituent C, or RdC(=O)- (where Rd has the same meaning as above). preferable.

R5b in formula (1-2) and formula (1-3) has the same meaning as R5 described above. That is, a halogen atom, a cyano group, a nitro group, a C1 to C6 alkyl group optionally substituted with a substituent C, a C1 to C6 haloalkyl group, a C3 to C8 cyclo group optionally substituted with a substituent C. Alkyl 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 halo Alkynyl 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 A C2 to C6 alkenyloxy group which may be optionally substituted, a C2 to C6 haloalkenyloxy group, a C3 to C6 alkynyloxy group which may be optionally substituted with substituent C, a C3 to C6 haloalkynyloxy group, RdC(=O)-(here, Rd has the same meaning as above), RdC(=O)O-(here, Rd has the same meaning as above), Rc-L-(here, Rd has the same meaning as above), , Rc and L have the same meanings as above), RaRbN- (where Ra and Rb have the same meanings as above), ReC(=O)N(Rf)- (where Re and Rf has the same meaning as above), RhON=C(Ri)- (where Rh and Ri have the same meaning as above), or a phenyl group which may be optionally substituted with 0 to 5 substituents D. (However, in the case of two or more substituents D, each is independent.)

Among these, R5b is a halogen atom, a cyano group, a C1 to C6 alkyl group optionally substituted with substituent C, a C1 to C6 haloalkyl group, and a C3 to C8 cycloalkyl group optionally substituted with substituent C. C2-C6 alkenyl group optionally substituted with substituent C, C2-C6 haloalkenyl group, C2-C6 alkynyl group optionally substituted with substituent C, C2-C6 haloalkynyl group, a C1 to C6 alkoxy group which may be optionally substituted with substituent C, a C2 to C6 alkenyloxy group which may be optionally substituted with substituent C, C3 to C6 which may be optionally substituted with substituent C an alkynyloxy group, RdC(=O)- (here, Rd has the same meaning as above), Rc-L- (here, Rc and L have the same meaning as above), RaRbN-( Here, Ra and Rb have the same meanings as above.), RhON=C(Ri)- (Here, Rh and Ri have the same meanings as above.), or 0 to 5 substitutions as appropriate with substituent D. A phenyl group that may be substituted (however, in the case of two or more substituents D, each is independent) is preferable,
In particular, R5b is a halogen atom, a cyano group, a C1-C6 alkyl group optionally substituted with substituent C, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group optionally substituted with substituent C. group, a C2-C6 alkenyl group optionally substituted with substituent C, a C2-C6 alkynyl group optionally substituted with substituent C, a C1-C6 alkenyl group optionally substituted with substituent C Alkoxy group, RdC(=O)- (here, Rd has the same meaning as above), Rc-L- (here, Rc and L have the same meaning as above), RhON=C(Ri )-(Here, Rh and Ri have the same meanings as above.), or a phenyl group that may be optionally substituted with 0 to 5 substituents D (however, in the case of two or more substituents D, each independently ) is preferred.

Preferred specific examples of each substituent for R5a and R5b in formula (1-1), formula (1-2) and formula (1-3) are the same as the preferred specific example described for R5.

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

A bond including a broken line in formula (1) represents a double bond or a single bond. A preferred bond containing the dashed line is a double bond.

（式中、Ｒ１、Ｒ２、Ｒ３、ｎ、Ｒ４、Ｒ５、ｍおよびＸ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。If the bond including the broken line in formula (1) is a double bond, formula (1a)

(In the formula, R1, R2, R3, n, R4, R5, m and X have the same meanings as in formula (1).) or a salt thereof.

（式中、Ｒ１、Ｒ２、Ｒ３、ｎ、Ｒ４、Ｒ５、ｍおよびＸ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。If the bond including the broken line in formula (1) is a single bond, formula (1b)

(In the formula, R1, R2, R3, n, R4, R5, m and X have the same meanings as in formula (1).) or a salt thereof.

The compound represented by formula (1b) is either the R form or the S form, or a mixture of the R form and the S form in any proportion.

The compound represented by formula (1) may have one or two axial asymmetries. The isomer ratio at this time is a mixture ratio of individual or arbitrary ratios, and is not particularly limited.

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

The compound represented by formula (1) may include geometric isomers. The isomer ratio at this time is a mixture ratio of individual or arbitrary ratios, and is not particularly limited.

The compound represented by formula (1) may be capable of forming a salt. 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, but there are no particular limitations as long as they can be used as agricultural and horticultural fungicides. There isn't.

"Substituent A" 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, RaRbN- (Here, Ra and Rb have the same meanings as above.) and Rc-L- (Here, Rc and L have the same meanings as above.).

Among these, the substituent A is preferably a cyano group, a C1 to C6 alkoxy group, or Rc-L- (where Rc and L have the same meanings as above),
Further, substituent A is preferably a cyano group or a C1 to C6 alkoxy group.

In addition, each term of substituent A is synonymous with the said definition.

Preferred specific examples of substituent A include hydroxyl group; cyano group;
As a C3 to C8 cycloalkyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group;
As C1 to C6 alkoxy groups, methoxy group, ethoxy group, propyloxy group, and isopropyloxy group;
As C1 to C6 haloalkoxy groups, difluoromethoxy group, trifluoromethoxy group, 2,2-difluoroethoxy group, 2,2,2-trifluoroethoxy group, 3,3-difluoropropyloxy group, and 3,3 ,3-trifluoropropyloxy group;
As a C3 to C8 cycloalkoxy group, a cyclopropyloxy group, a cyclobutoxy group, a cyclopentyloxy group, and a cyclohexyloxy group;
RaRbN- (where Ra and Rb have the same meanings as above) includes 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- (where Rc and L have the same meanings as above), a methylthio group, methanesulfinyl group, methanesulfonyl group, ethylthio group, ethanesulfinyl group, ethanesulfonyl group, trifluoromethylthio group, Examples include trifluoromethanesulfinyl group and trifluoromethanesulfonyl group.

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

"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 these, substituent B is preferably a cyano group or a C1 to C6 alkoxy group.

In addition, each term of substituent B has the same meaning as the said definition.

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

Regarding more preferred specific examples of substituent B, cyano group;
As a C1 to C6 alkoxy group, a methoxy group and an ethoxy group;
As C1 to C6 haloalkoxy groups, difluoromethoxy group, trifluoromethoxy group, 2,2-difluoroethoxy group, and 2,2,2-trifluoroethoxy group;
Examples of the C3 to C8 cycloalkoxy group include a cyclopropyloxy group and a cyclobutoxy group.

"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- (here, Ra and Rb have the same meanings as above), Rc-L- (here, Rc and L have the same meanings as above), RdC (=O )-(here, Rd has the same meaning as above) and represents at least one member selected from the group consisting of a 3- to 6-membered ring group containing 1 to 2 oxygen atoms.

Among these, substituent C is a hydroxyl group, a cyano group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, or Rc-L- (where Rc and L are as defined above). ) is preferred,
In particular, substituent C is preferably a hydroxyl group or a C1 to C6 alkoxy group.

In addition, each term of substituent C has the same meaning as the said definition.

Preferred specific examples of substituent C include hydroxyl group; cyano group;
As a C3 to C8 cycloalkyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group;
As C1 to C6 alkoxy groups, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butoxy group, isobutoxy group, and t-butoxy group;
As C1 to C6 haloalkoxy groups, difluoromethoxy group, trifluoromethoxy group, 2,2-difluoroethoxy group, 2,2,2-trifluoroethoxy group, 3,3-difluoropropyloxy group, and 3,3 ,3-trifluoropropyloxy group;
As a C3 to C8 cycloalkoxy group, a cyclopropyloxy group, a cyclobutoxy group, a cyclopentyloxy group, and a cyclohexyloxy group;
As a C2 to C6 alkoxyalkoxy group, a methoxymethoxy group, an ethoxymethoxy group, a methoxyethoxy group, an ethoxyethoxy group, and a methoxypropyloxy group;
RaRbN- (where Ra and Rb have the same meanings as above) includes 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, piperidinyl group, and morpholyl group ;
Rc-L- (where Rc and L have the same meanings as above), a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, a trifluoromethanesulfinyl group, and a trifluoromethanesulfonyl group;
RdC(=O)- (wherein Rd has the same meaning as above), formyl group, acetyl group, methoxyacetyl group, cyanoacetyl group, propionyl group, difluoroacetyl group, trifluoroacetyl group, cyclopropane Carbonyl 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, dimethyl Aminocarbonyl group, ethylmethylaminocarbonyl group, diethylaminocarbonyl group, (methoxymethyl)methylaminocarbonyl group, (2-methoxyethyl)methylaminocarbonyl group, (cyanomethyl)methylaminocarbonyl group, (2-cyanoethyl)methylaminocarbonyl group group, 2,2-difluoroethylaminocarbonyl group, 2,2,2-trifluoroethylaminocarbonyl group, cyclopropylaminocarbonyl group, (cyclopropyl)methylaminocarbonyl group, pyrrolidinylcarbonyl group, and piperidinyl group carbonyl group;
Examples of the 3- to 6-membered ring group containing 1 to 2 oxygen atoms include an oxolanyl group, an oxanyl group, a 1,3-dioxolanyl group, and a 1,3-dioxanyl group.

More preferred specific examples of substituent C include hydroxyl group; cyano group;
As a C3 to C8 cycloalkyl group, a cyclopropyl group and a cyclobutyl group;
As a C1 to C6 alkoxy group, a methoxy group and an ethoxy group;
As a C1 to C6 haloalkoxy group, a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group;
As a C3 to C8 cycloalkoxy group, a cyclopropyloxy group, a cyclobutoxy group;
As a C2 to C6 alkoxyalkoxy group, a methoxymethoxy group, an ethoxymethoxy group, a methoxyethoxy group, and an ethoxyethoxy group;
RaRbN- (where Ra and Rb have the same meanings as above), a dimethylamino group, an ethylmethylamino group, and a diethylamino group;
Rc-L- (wherein Rc and L have the same meanings as above), a methylthio group, a methanesulfinyl group, and a methanesulfonyl group;
RdC(=O)- (wherein Rd has the same meaning as above), 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;
Examples of the 3- to 6-membered ring group containing 1 to 2 oxygen atoms include a 1,3-dioxolanyl group and a 1,3-dioxanyl group.

"Substituent D" in formula (1) is a hydroxyl group, a cyano group, a halogen atom, a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, a C1 to C6 alkoxy group, RaRbN- (where Ra and Rb has the same meaning as above) and Rc-L- (where Rc and L have the same meanings as above).

Among them, the substituent D is a halogen atom, a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, a C1 to C6 alkoxy group, RaRbN- (where Ra and Rb are as defined above), or Rc-L- (where Rc and L have the same meanings as above) is preferred,
In particular, substituent D is preferably a halogen atom, a C1-C6 alkyl group, or a C1-C6 haloalkyl group.

In addition, each term of substituent D has the same meaning as the said definition.
Preferred specific examples of substituent D include hydroxyl group; cyano group;
As halogen atoms, fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms;
As C1 to C6 alkyl groups, methyl group, ethyl group, propyl group, isopropyl group, butyl group, and isobutyl group;
As C1 to C6 haloalkyl groups, difluoromethyl group, trifluoromethyl group, 2,2-difluoroethyl group, and 2,2,2-trifluoroethyl group;
As C1 to C6 alkoxy groups, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butoxy group, isobutoxy group, and t-butoxy group;
RaRbN- (where Ra and Rb have the same meanings as above) includes 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, piperidinyl group, and morpholyl group ;
and Rc-L- (where Rc and L have the same meanings as above), a methylthio group, methanesulfinyl group, methanesulfonyl group, ethylthio group, ethanesulfinyl group, ethanesulfonyl group, trifluoromethylthio group, Examples include trifluoromethanesulfinyl group and trifluoromethanesulfonyl group.

More preferred specific examples of substituent D include hydroxyl group; cyano group;
As halogen atoms, fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms;
As C1 to C6 alkyl groups, methyl group, ethyl group, propyl group, and isopropyl group;
As a C1 to C6 haloalkyl group, a difluoromethyl group and a trifluoromethyl group;
As a C1 to C6 alkoxy group, a methoxy group and an ethoxy group;
RaRbN- (where Ra and Rb have the same meanings as above), a dimethylamino group, an ethylmethylamino group, and a diethylamino group;
and Rc-L- (where Rc and L have the same meanings as above) include a methylthio group, a methanesulfinyl group, and a methanesulfonyl group.

All compounds obtained by arbitrarily combining the preferred ranges of R1, R2, R3, R4, R5, m, n, The range is also described in this specification as the range of the compound represented by formula (1) of the present invention.

を表し、Ａｚは下記部分構造

を表す。Next, specific compounds of the present invention have structural formulas P-1 to P-28 shown in Table 1, structural formulas Ph (Ph-1 to Ph-302) shown in Table 2, and structures shown in Table 3. It is represented by a combination with the formula Az (Az1-001 to Az1-082, Az2-001 to Az2-082, Az3-001 to Az3-832). In addition, X in Table 1 represents an oxygen atom or a sulfur atom, the bond including the broken line represents a double bond or a single bond, and Ph represents the following partial structure.

, and Az is the following partial structure

represents.

These compounds are for illustrative purposes only, and the invention is not limited thereto.

In Table 3, the partial structure represented by Az1 is represented by the following formula (Az1).

In Table 3, the partial structure represented by Az2 is represented by the following formula (Az2).

In Table 3, the partial structure represented by Az3 is represented by the following formula (Az3).

The method for producing the compound represented by formula (1) is illustrated below. The method for producing the compound of the present invention is not limited to Production Method A to Production Method X.

式中、Ｒ４Ａは、水素原子、ハロゲン原子、シアノ基、ニトロ基、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、
Ｒｃ－Ｌ－（ここで、ＲｃおよびＬは、前記と同義である。）、ＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）、またはＲｇＣ（＝Ｏ）－（ここで、Ｒｇは、前記と同義である。）を表し、Ｒ７は、水素原子またはＣ１～Ｃ６のアルキル基を表し、Ｒ６ａは、水素原子、ニトロ基、またはアミノ基を表し、ｐは、０～２の整数（ただし、ｐが２の場合、２置換のＲ５は、それぞれ独立している。）を表し、Ｒ２、Ｒ３、Ｒ５、ｎ、およびＸは前記と同義である。[Manufacturing method A]

In the formula, R4A is a hydrogen atom, a halogen atom, a cyano group, a nitro group, a C1-C6 alkyl group optionally substituted with substituent A, a C1-C6 haloalkyl group, optionally substituted with substituent A. a C3-C8 cycloalkyl group that may be optionally substituted with a substituent A, a C2-C6 alkenyl group that may be optionally substituted with a substituent A, a C2-C6 haloalkenyl group that may be optionally substituted with a substituent A; group, C2 to C6 haloalkynyl group, C1 to C6 alkoxy group optionally substituted with substituent A, C1 to C6 haloalkoxy group, C3 to C8 cyclo optionally substituted with substituent A Alkoxy group, C2-C6 alkenyloxy group optionally substituted with substituent A, C2-C6 haloalkenyloxy group, C3-C6 alkynyloxy group optionally substituted with substituent A, C3- C6 haloalkynyloxy group,
Rc-L- (here, Rc and L have the same meanings as above), RaRbN- (here, Ra and Rb have the same meanings as above), or RgC(=O)-(here, , Rg are as defined above), R7 represents a hydrogen atom or a C1 to C6 alkyl group, R6a represents a hydrogen atom, a nitro group, or an amino group, and p is 0 to 2. (However, when p is 2, each of the two substituted R5s is independent.), and R2, R3, R5, n, and X are as defined above.

Production method A is a method for synthesizing a production intermediate represented by formula (6), in which a compound represented by formula (4) and a compound represented by formula (5) are combined in a solvent in the presence of a base. This is a manufacturing method that involves reacting with

The compound represented by formula (4) used in this reaction can be synthesized according to known methods and reference examples.

The compound represented by formula (5) used in this reaction can be obtained as a commercially available product or can be 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. However, it is usually 1 equivalent or more and 3 equivalents or less.

The bases used in this reaction include inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate, and tripotassium phosphate; metal alkoxides such as sodium methoxide, sodium ethoxide, sodium t-butoxide, and potassium t-butoxide; These include organic bases such as triethylamine, tributylamine, 1,8-diazabicyclo[5.4.0]-7-undecene, and 1,4-diazabicyclo[2.2.2]octane.

The base used in this reaction can be carried out in a catalytic amount and is not particularly limited as long as the desired reaction proceeds, but it is usually used for the compound represented by formula (4). The amount is 0.01 equivalent or more and 3 equivalents or less.

The 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, butyl acetate, nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, 1,3-dimethyl Urea solvents such as -2-imidazolidinone, halogen solvents such as dichloromethane, dichloroethane, chloroform, carbon tetrachloride, sulfur solvents such as dimethyl sulfoxide and sulfolane, ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, etc. can be mentioned. These solvents can be used alone or in a mixture of two or more in any ratio.

The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but it is usually at least 3 times and no more than 200 times the weight of the compound represented by formula (4). be.

The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually -50°C to 150°C or below the boiling point of the solvent.

As a post-treatment of the reaction, it is possible to perform a liquid separation operation by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, use an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, etc., an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, etc., or a saline solution. etc. can be used arbitrarily. During the separation operation, benzene solvents such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, 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, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. It is possible to add. Moreover, these solvents can be used alone or two or more kinds can be mixed in any ratio. The number of separations is not particularly limited and can be performed depending on the desired purity and yield.

Moisture can be removed from the reaction mixture containing the compound represented by formula (6) obtained above using a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential. The reaction mixture containing the compound represented by ) can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (6) obtained after evaporation of the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. using an appropriate solvent. It may be set as appropriate depending on the desired purity.

式中、Ｒ７ａはＣ１～Ｃ６のアルキル基を表し、Ｒ２、Ｒ３、Ｒ４Ａ、Ｒ５、Ｒ６ａ、ｎ、ｐおよびＸは前記と同義である。[Manufacturing method B]

In the formula, R7a represents a C1 to C6 alkyl group, and R2, R3, R4A, R5, R6a, n, p and X are as defined above.

Production method B is a method for producing a production intermediate represented by formula (6b) among the compounds represented by formula (6), in which the compound represented by formula (6a) is prepared under acidic conditions or with a base. This is a production method that involves reacting in a solvent under specific conditions.

First, the reaction under acidic conditions will be explained.

Examples of 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 is no particular restriction as long as the desired reaction proceeds.

The amount of acid used in this reaction may be a catalytic amount and is not particularly limited as long as the desired reaction proceeds, but it is usually 0.01 It is more than equivalent. Furthermore, 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, but includes aqueous solvents, acidic solvents such as acetic acid and methanesulfonic acid, diethyl ether, diisopropyl ether, methyl-t- 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. Examples include urea-based solvents, dichloromethane, dichloroethane, chloroform, and halogen-based solvents such as carbon tetrachloride. These solvents can be used alone or in a mixture of two or more in any ratio.

The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but it is usually 3 times or more and 200 times or less by weight relative to the compound represented by formula (6a). be.

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

Next, the reaction under basic conditions will be explained.

The base used in this reaction is exemplified by inorganic bases such as lithium hydroxide, sodium hydroxide, potassium hydroxide, etc., 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 (6a), as long as the desired reaction proceeds, but it is usually 1 equivalent or more. It is less than the equivalent amount.

The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but includes water, ethers such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane. alcoholic solvents such as methanol, ethanol, isopropanol, benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, nitriles such as acetonitrile amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, dichloromethane, dichloroethane, chloroform, Examples include halogenated solvents such as carbon tetrachloride. These solvents can be used alone or in a mixture of two or more in any ratio.

The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but it is usually 3 times or more and 200 times or less by weight relative to the compound represented by formula (6a). 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 -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 reactions under acidic conditions and reactions under basic conditions. A liquid separation operation can be performed by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, use an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, etc., an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, etc., or saline solution. etc. can be used arbitrarily. During the separation operation, benzene solvents such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, 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, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. It is possible to add. Moreover, these solvents can be used alone or two or more kinds can be mixed in any ratio. The number of separations is not particularly limited and can be performed depending on the desired purity and yield.

Moisture can be removed from the reaction mixture containing the compound represented by formula (6b) obtained above using a desiccant such as sodium sulfate or magnesium sulfate, but this is not essential.

The reaction mixture containing the compound represented by formula (6b) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (6b) obtained after evaporation of the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. using an appropriate solvent. It may be set as appropriate depending on the desired purity.

（式中、Ｒ２、Ｒ３、Ｒ４Ａ、Ｒ５、Ｒ６ａ、ｎ、ｐおよびＸは前記と同義である。）で表される異性体も含む。The compound represented by formula (6b) is represented by formula (6b')

(In the formula, R2, R3, R4A, R5, R6a, n, p and X have the same meanings as above.) It also includes isomers represented by the formula.

The compound represented by formula (6b') can be handled in the same manner as the compound represented by formula (6b), and production method C can be applied. Furthermore, although the compound represented by formula (6b') contains an asymmetric carbon, the isomer may be used alone or as a mixture at any ratio. Furthermore, a mixture of the compound represented by formula (6b) and the compound represented by formula (6b') may be used, and the isomer mixing ratio may be a single one or a mixture at any ratio.

式中、Ｒ１ａは、水素原子、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、前記と同義である。）を表し、Ｒ２、Ｒ３、Ｒ４Ａ、Ｒ５、Ｒ６ａ、Ｒ７、ｎ、ｐおよびＸは前記と同義である。[Manufacturing method C]

In the formula, R1a is a hydrogen atom, a hydroxyl group, a cyano group, a C1 to C6 alkyl group optionally substituted with a substituent A, a C1 to C6 haloalkyl group, or a C3 to C6 optionally substituted with a substituent A. C8 cycloalkyl group, C2-C6 alkenyl group optionally substituted with substituent A, C2-C6 haloalkenyl group, C2-C6 alkynyl group optionally substituted with substituent A, C2- C6 haloalkynyl group, C1 to C6 alkoxy group optionally substituted with substituent A, C1 to C6 haloalkoxy group, C3 to C8 cycloalkoxy group optionally substituted with substituent A, substitution C2-C6 alkenyloxy group optionally substituted with group A, C2-C6 haloalkenyloxy group, C3-C6 alkynyloxy group optionally substituted with substituent A, C3-C6 haloalkynyl represents an oxy group or RaRbN- (where Ra and Rb are as defined above), and R2, R3, R4A, R5, R6a, R7, n, p and X are as defined above.

Production method C is a method for obtaining a compound represented by formula (3a) containing a production intermediate of the compound of the present invention, in which a compound represented by formula (6) and R1a-NH ₂ are mixed in the presence of an acid. This is a manufacturing method that involves reacting with

R1a-NH ₂ used in this reaction can be obtained as a commercial product or produced by a known method. R1a-NH ₂ 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 desired reaction proceeds.

R1a-NH ₂ used in this reaction may be used in an amount of 1 equivalent or more relative to the compound represented by formula (6), and is not particularly limited as long as the desired reaction proceeds, but usually, The amount is 1 equivalent or more and 200 equivalents or less.

Examples of acids 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, and there is no particular limitation as long as the desired reaction proceeds. but preferably acetic acid. Further, when using a salt of R1a-NH ₂ and an acidic compound, the use of an acid is not essential.

The amount of acid used in this reaction may be 1 equivalent or more relative to R1a-NH ₂ and is not particularly limited as long as the desired reaction proceeds, but it is usually 1 equivalent or more and 200 equivalents or less. It is. Furthermore, when the acid used is a liquid, it can also be used as a solvent.

Although a solvent can be used in this reaction, it is not necessarily essential.

The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but includes acidic solvents such as acetic acid and methanesulfonic acid, diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxy Ether solvents such as ethane, tetrahydrofuran, dioxane, alcohol solvents such as methanol, ethanol, isopropanol, benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, ethyl acetate, isopropyl acetate, butyl acetate, etc. Ester solvents, nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, and urea solvents such as 1,3-dimethyl-2-imidazolidinone. Solvents include halogenated solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride. These solvents can be used alone or in a mixture of two or more in any ratio. As the solvent, preferably an acidic solvent is used, and more preferably acetic acid is used.

The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but it is usually at least 3 times and no more than 200 times the weight of the compound represented by formula (6). be.

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

As a post-treatment of the reaction, it is possible to perform a liquid separation operation by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, use an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, etc., an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, etc., or a saline solution. etc. can be used arbitrarily. During the separation operation, benzene solvents such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, 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, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. It is possible to add. Moreover, these solvents can be used alone or two or more kinds can be mixed in any ratio. The number of separations is not particularly limited and can be performed depending on the desired purity and yield.

Moisture can be removed from the reaction mixture containing the compound represented by formula (3a) obtained above using a desiccant such as sodium sulfate or magnesium sulfate, but this is not essential.

The reaction mixture containing the compound represented by formula (3a) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (3a) obtained after evaporation of the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. using an appropriate solvent. It may be set as appropriate depending on the desired purity.

（式中、Ｒ６は、ニトロ基またはアミノ基を表し、Ｒ２、Ｒ３、Ｒ４Ａ、Ｒ５、ｎ、ｐ、およびＸは、前記と同義である。）で表される化合物は、本発明の式（１）で表される化合物を得る有用な製造中間体となりうる。According to production method C, a compound that can be produced when R1a represents a hydrogen atom and R6a represents a nitro group or an amino group in the compound represented by formula (3a), that is, formula (3)

(In the formula, R6 represents a nitro group or an amino group, and R2, R3, R4A, R5, n, p, and X are as defined above.) The compound represented by the formula ( It can be a useful production intermediate for obtaining the compound represented by 1).

を表す。Specific examples of the production intermediate represented by formula (3) are combinations of structural formulas J-1 to J-8 shown in Table 4 and structural formulas Ph (Ph-1 to Ph-302) shown in Table 2. Represented by In addition, R5, R6, p and X in Table 4 are synonymous with formula (3), and Ph has the following partial structure.

represents.

These compounds are for illustrative purposes only, and the production intermediate of the present invention is not limited thereto.

式中、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、Ｒ３、Ｒ４Ａ、Ｒ５、Ｒ６ａ、ｎ、ｐおよびＸは前記と同義である。[Manufacturing method D]

In the formula, Lv represents a leaving group such as a methanesulfonyl group, a trifluoromethanesulfonyl group, a p-toluenesulfonyl group, or a halogen atom, and R1, R2, R3, R4A, R5, R6a, n, p and X are as described above. are synonymous.

Production method D is a method for obtaining a compound represented by formula (2b) containing a production intermediate of the compound of the present invention, in which the production intermediate represented by formula (3b) and R1-Lv are combined with a base. This is a manufacturing method that includes reacting in the presence of a solvent.

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

The amount of R1-Lv used in this reaction may be 1 equivalent or more relative to the compound represented by formula (3b), and is not particularly limited as long as the desired reaction proceeds, but usually , 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, but there are no particular limitations as long as the desired reaction proceeds. It will not be done.

The amount of base used in this reaction is not particularly limited as long as it is 1 equivalent or more based on the compound represented by formula (3b), and as long as the desired reaction proceeds, but it is usually 1 equivalent or more. The amount is equal to or more than 10 equivalents.

The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds; Alcohol solvents such as methanol, ethanol, isopropanol, benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, 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, dichloromethane, dichloroethane, chloroform, carbon tetrachloride Examples include halogen-based solvents such as, sulfur-based solvents such as dimethyl sulfoxide and sulfolane, and ketone-based solvents such as acetone, methyl ethyl ketone, and methyl isobutyl ketone. These solvents can be used alone or in a mixture of two or more in any ratio.

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

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

As a post-treatment of the reaction, it is possible to perform a liquid separation operation by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, use an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, etc., an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc., thiosulfuric acid, etc. An aqueous solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved, or a saline solution can be arbitrarily used. During the separation operation, benzene solvents such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, 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, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. It is possible to add. Moreover, these solvents can be used alone or two or more kinds can be mixed in any ratio. The number of separations is not particularly limited and can be performed depending on the desired purity and yield.

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

The reaction mixture containing the compound represented by formula (2b) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (2b) obtained after evaporation of the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. using an appropriate solvent. It may be set as appropriate depending on the desired purity.

式中、ＳＲは硫黄化剤を表し、Ｒ１、Ｒ２、Ｒ３、Ｒ４Ａ、Ｒ５、Ｒ６ａ、ｎおよびｐは前記と同義である。[Manufacturing method E]

In the formula, SR represents a sulfurizing agent, and R1, R2, R3, R4A, R5, R6a, n and p are as defined above.

Manufacturing method E is a manufacturing method for obtaining a compound represented by formula (2b-b) among the manufacturing intermediates represented by formula (2b), which comprises a compound represented by formula (2b-a) and a compound represented by formula (2b-a). This is a manufacturing method that includes reacting a sulfurizing agent (SR) in a solvent.

Examples of the sulfating agent used in this reaction include Lawson's reagent (2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide).

The amount of the sulfurizing agent used in this reaction may be 0.5 equivalent or more relative to the compound represented by formula (2b-a), and is not particularly limited as long as the desired reaction proceeds. However, it is usually 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; Examples include benzene-based solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene. These solvents can be used alone or in a mixture of two or more in any ratio.

The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but it is usually 3 times or more by weight or more and 200 times by weight relative to the compound represented by formula (2b-a). It is as follows.

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

As a post-treatment of the reaction, a liquid separation operation can be performed by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, use an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, etc., an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, etc., or a saline solution. etc. can be used arbitrarily. During the separation operation, benzene solvents such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, 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, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. It is possible to add. Moreover, these solvents can be used alone or two or more kinds can be mixed in any ratio. The number of separations is not particularly limited and can be performed depending on the desired purity and yield. Moreover, in this reaction, a liquid separation operation is not essential.

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

The reaction mixture containing the compound represented by formula (2b-b) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (2b-b) obtained after evaporation of the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. using an appropriate solvent. It may be set as appropriate depending on the desired purity.

式中、Ｏｘは酸化剤を表し、Ｒ１、Ｒ２、Ｒ３、Ｒ４Ａ、Ｒ５、Ｒ６ａ、ｎ、ｐおよびＸは前記と同義である。[Manufacturing method F]

In the formula, Ox represents an oxidizing agent, and R1, R2, R3, R4A, R5, R6a, n, p and X are as defined above.

Production method F is a production method for obtaining a compound represented by formula (2a) containing a production intermediate of the compound of the present invention, in which a compound represented by formula (2b) and an oxidizing agent (Ox) are mixed in a solvent. This is a manufacturing method that involves reacting inside a container.

In the compound represented by formula (2b), R6a is preferably a nitro group.

As the oxidizing agent used in this reaction, metal oxides, benzoquinones, a combination of a radical initiator and a halogenating agent, etc. can be used.

A method in which the oxidizing agent is a metal oxide will be described below.

Examples of the metal oxide used in this reaction include manganese dioxide and the like.

The amount of the oxidizing 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 (2b), as long as the desired reaction proceeds, but it is usually 1 equivalent or more. The amount is equal to or more than 200 equivalents.

The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but includes benzene-based solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene, dichloromethane, dichloroethane, chloroform, Examples include halogenated solvents such as carbon tetrachloride. These solvents can be used alone or in a mixture of two or more in any ratio.

The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but it is usually 3 times or more and 200 times or less by weight relative to the compound represented by formula (2b). be.

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

As a post-treatment of the reaction, undissolved metals can be removed by filtration. Furthermore, it is possible to perform a liquid separation operation by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, use an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, etc., an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, etc., or a saline solution. etc. can be used arbitrarily. During the separation operation, benzene solvents such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, 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, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. It is possible to add. Moreover, these solvents can be used alone or two or more kinds can be mixed in any ratio. The number of separations is not particularly limited and can be performed depending on the desired purity and yield. Moreover, in this reaction, a liquid separation operation is not essential.

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

The reaction mixture containing the compound represented by formula (2a) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (2a) obtained after evaporation of the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. using an appropriate solvent. It may be set as appropriate depending on the desired purity.

The method using benzoquinones as the oxidizing agent will be described below.

Examples of the benzoquinones used in this reaction include 2,3-dichloro-5,6-dicyano-p-benzoquinone.

The amount of the oxidizing agent used in this reaction is not particularly limited as long as the amount of the oxidizing agent is 1 equivalent or more relative to the compound represented by formula (2b), as long as the desired reaction proceeds, but it is usually 1 equivalent. The amount is not less than 20 equivalents and not more than 20 equivalents.

The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but includes benzene-based solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene, dichloromethane, dichloroethane, chloroform, Examples include halogenated solvents such as carbon tetrachloride. These solvents can be used alone or in a mixture of two or more in any ratio.

The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but it is usually 3 times or more and 200 times or less by weight relative to the compound represented by formula (2b). be.

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

As a post-treatment of the reaction, it is possible to perform a liquid separation operation by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, use an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, etc., an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, etc., or a saline solution. etc. can be used arbitrarily. During the separation operation, benzene solvents such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, 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, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. It is possible to add. Moreover, these solvents can be used alone or two or more kinds can be mixed in any ratio. The number of separations is not particularly limited and can be performed depending on the desired purity and yield. Moreover, in this reaction, a liquid separation operation is not essential.

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

The reaction mixture containing the compound represented by formula (2a) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (2a) obtained after evaporation of the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. using an appropriate solvent. It may be set as appropriate depending on the desired purity.

A method in which the oxidizing agent is a combination of a radical initiator and a halogenating agent will be described below.

Examples of the radical initiator used in this reaction include azobisisobutyronitrile, 2,2'-azobis(4-methoxy-2,4-dimethylvaleronitrile), and benzoyl peroxide.

The amount of the radical initiator used in this reaction is not particularly limited as long as it is 0.01 equivalent or more relative to the compound represented by formula (2b), as long as the desired reaction proceeds. Usually, it is 0.01 equivalent or more and 1 equivalent or less.

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

The amount of halogenating agent used in this reaction is not particularly limited as long as it is 1.0 equivalent or more relative to the compound represented by formula (2b), as long as the desired reaction proceeds. Usually, it is 1 equivalent or more and 3 equivalents or less. However, the amount of the halogenating agent containing hydantoin is not particularly limited as long as it is 0.5 equivalent or more and the desired reaction proceeds, and is usually 0.5 equivalent or more and 1.5 equivalent or less. be.

The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but includes halogenated benzene solvents such as chlorobenzene and dichlorobenzene, and ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate. 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 alone or in a mixture of two or more in any ratio.

The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but it is usually 3 times or more and 200 times or less by weight relative to the compound represented by formula (2b). be.

The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually at least 20°C and at most 150°C or at most the boiling point of the solvent.

As a post-treatment of the reaction, it is possible to perform a liquid separation operation by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, use an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, etc., an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc., thiosulfuric acid, etc. An aqueous solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved, or a saline solution can be arbitrarily used. During the separation operation, benzene solvents such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, diethyl ether, diisopropyl ether, methyl- It is possible to add solvents that are incompatible 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. It is possible. Moreover, these solvents can be used alone or two or more kinds can be mixed in any ratio. The number of separations is not particularly limited and can be performed depending on the desired purity and yield.

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

The reaction mixture containing the compound represented by formula (2a) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (2a) obtained after evaporation of the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. using an appropriate solvent. It may be set as appropriate depending on the desired purity.

式中、Ｒ４ａはハロゲン原子を表し、ＨａｌＲはハロゲン化剤を表し、Ｒ１、Ｒ２、Ｒ３、Ｒ５、Ｒ６、ｎ、ｐおよびＸは前記と同義である。[Manufacturing method G]

In the formula, R4a represents a halogen atom, HalR represents a halogenating agent, and R1, R2, R3, R5, R6, n, p and X are as defined above.

Manufacturing method G is a manufacturing method for obtaining a compound represented by formula (2a-b) in which R4a represents a halogen atom among the manufacturing intermediates represented by formula (2a), This is a manufacturing method that includes reacting a compound represented by the above with a halogenating agent (HalR) in a solvent.

The halogenating agents used in this reaction include selectrofluor (N-fluoro-N'-triethylenediamine bis(tetrafluoroborate)), N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, , 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 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 (2a-a), as long as the desired reaction proceeds. Usually, 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 equivalent or more and the desired reaction proceeds, and is usually 1 equivalent or more and 5 equivalents or less.

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

When the halogenating agent used in this reaction is an iodizing agent, the amount of acid used is 0.01 equivalent or more with respect to the compound represented by formula (2a-a), so that the desired reaction can be achieved. Although there is no particular restriction as long as it proceeds, it is usually 0.1 equivalent or more and 3 equivalents or less.

The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but includes acidic solvents such as sulfuric acid, acetic acid, trifluoroacetic acid, methanesulfonic acid, and trifluoromethanesulfonic acid, diethyl ether, etc. , 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 , ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, 1,3- Examples include urea solvents such as dimethyl-2-imidazolidinone, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride. These solvents can be used alone or in a mixture of two or more in any ratio.

The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but it is usually 3 times or more by weight or more and 200 times by weight relative to the compound represented by formula (2a-a). It is as follows.

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

As a post-treatment of the reaction, it is possible to perform a liquid separation operation by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, use an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, etc., an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc., thiosulfuric acid, etc. An aqueous solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved, or a saline solution can be arbitrarily used. During the separation operation, benzene solvents such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, 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, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. It is possible to add. Moreover, these solvents can be used alone or two or more kinds can be mixed in any ratio. The number of separations is not particularly limited and can be performed depending on the desired purity and yield.

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

The reaction mixture containing the compound represented by formula (2a-b) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (2a-b) obtained after evaporation of the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. using an appropriate solvent. It may be set as appropriate depending on the desired purity.

式中、Ｊは酸素原子または硫黄原子を表し、Ｊが酸素原子の場合、Ｒ８ｃ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Ｃ３～Ｃ６のアルキニル基、またはＣ３～Ｃ６のハロアルキニル基を表し、Ｊが硫黄原子の場合、Ｒ８ｃ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、Ｑは水素原子または金属を表し、Ｒ１、Ｒ２、Ｒ３、Ｒ４ａ、Ｒ５、Ｒ６ａ、ｎ、ｐおよびＸは前記と同義である。[Manufacturing method H]

In the formula, J represents an oxygen atom or a sulfur atom, and when J is an oxygen atom, R8c is a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, or a C1 to C6 haloalkyl group, which may be optionally substituted with a substituent A. A C3 to C8 cycloalkyl group which may be optionally substituted, a C2 to C6 alkenyl group which may be optionally substituted with substituent A, a C2 to C6 haloalkenyl group, a C3 which may be optionally substituted with substituent A. ~ Represents a C6 alkynyl group or a C3 to C6 haloalkynyl group, and when J is a sulfur atom, R8c represents a C1 to C6 alkyl group or a C1 to C6 haloalkyl group, and Q represents a hydrogen atom or a metal. , R1, R2, R3, R4a, R5, R6a, n, p and X have the same meanings as above.

Production method H is a production intermediate represented by formula (2a), in which J represents an oxygen atom or a sulfur atom, and when J is an oxygen atom, R8c may be optionally substituted with a substituent A. C6 alkyl group, C1 to C6 haloalkyl group, C3 to C8 cycloalkyl group optionally substituted with substituent A, C2 to C6 alkenyl group optionally substituted with substituent A, C2 to C6 represents a haloalkenyl group, a C3-C6 alkynyl group optionally substituted with substituent A, or a C3-C6 haloalkynyl group, and when J is a sulfur atom, R8c is a C1-C6 alkyl group or C1 - A method for synthesizing a compound represented by formula (2a-c) representing a C6 haloalkyl group, wherein the compound represented by formula (2a-b) and R8c-J-Q are combined in the presence of transition metals. Below is a manufacturing method including obtaining the compound by a coupling reaction in a solvent.

In the compound represented by formula (2a-b), R4a is preferably a chlorine atom, a bromine atom, or an iodine atom.

R8c-JQ used in this reaction is available as a commercial product or can be produced by a known method. Preferred Q is a hydrogen atom or an alkali metal such as sodium or potassium.

The amount of R8c-J-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 (2a-b), as long as the desired reaction proceeds. . When Q is a hydrogen atom, it can also be used as a solvent.

The transition metals used in this reaction may have a ligand, such as palladium acetate, [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride, tris(dibenzylideneacetone)dipalladium, tetrakis( These include palladiums such as triphenylphosphine)palladium and bis(triphenylphosphine)palladium dichloride.

The amount of transition metals used in this reaction is 0.001 equivalent or more and 1 equivalent or less relative to the compound represented by formula (2a-b), but is not particularly limited as long as the desired reaction proceeds. It never happens.

In order to proceed with this reaction efficiently, triphenylphosphine, 1,1'-bis(diphenylphosphino)ferrocene, 2-dicyclohexylphosphino-2'4'6'-triisopropylbiphenyl, 2-di-t A phosphine ligand such as -butylphosphino-2'4'6'-triisopropylbiphenyl can be added.

The amount of 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 (2a-b), but is particularly limited as long as the desired reaction proceeds. It will not be done.

The bases used in this reaction include inorganic bases such as sodium carbonate, potassium carbonate, and cesium carbonate, and organic bases such as triethylamine, tributylamine, and diisopropylethylamine. However, when Q is an alkali metal, the base is not essential.

The amount of 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 (2a-b), as long as the desired reaction proceeds, but usually, It is 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, but R8c-J-H (wherein R8c has the same meaning as above and J is an oxygen atom). ), ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, etc. can be mentioned. These solvents can be used alone or in a mixture of two or more in any ratio.

The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but it is usually 3 times or more by weight or more and 200 times by weight relative to the compound represented by formula (2a-b). It is as follows.

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

As a post-treatment of the reaction, it is possible to perform a liquid separation operation by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, use an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, etc., an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, etc., or a saline solution. etc. can be used arbitrarily. During the separation operation, benzene solvents such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, 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, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. It is possible to add. Moreover, these solvents can be used alone or two or more kinds can be mixed in any ratio. The number of separations is not particularly limited and can be performed depending on the desired purity and yield. It is also possible to remove insoluble matter by performing a filtration operation, but this is not essential.

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

The reaction mixture containing the compound represented by formula (2a-c) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (2a-c) obtained after evaporation of the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. using an appropriate solvent. It may be set as appropriate depending on the desired purity.

式中、Ｒ８ｄ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Ｃ２～Ｃ６のアルケニル基、またはＣ２～Ｃ６のハロアルケニル基を表し、Ｒ８ｄ－Ｂは有機ボロン酸類を表し、Ｒ１、Ｒ２、Ｒ３、Ｒ４ａ、Ｒ５、Ｒ６ａ、ｎ、ｐおよびＸは前記と同義である。[Manufacturing method I]

In the formula, R8d is a C1-C6 alkyl group optionally substituted with substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with substituent A, substituent A represents a C2 to C6 alkenyl group or a C2 to C6 haloalkenyl group which may be optionally substituted, R8d-B represents an organic boronic acid, R1, R2, R3, R4a, R5, R6a, n, p and X have the same meanings as above.

Production method I is a production intermediate represented by formula (2a), in which R8d is a C1 to C6 alkyl group optionally substituted with a substituent A, a C1 to C6 haloalkyl group, or a C1 to C6 haloalkyl group, optionally substituted with a substituent A. Represented by formula (2a-d) which is an optionally substituted C3 to C8 cycloalkyl group, a C2 to C6 alkenyl group optionally substituted with substituent A, or a C2 to C6 haloalkenyl group A method for synthesizing a compound, comprising Suzuki-Miyaura coupling in which a compound represented by formula (2a-b) and an organic boronic acid (R8d-B) are reacted in a solvent in the presence of a transition metal and a base. This is a manufacturing method including obtaining by.

In formulas (2a-b), R4a is preferably a chlorine atom, a bromine atom, or an iodine atom.

R8d-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 commercially available product or produced by a known method.

The amount of R8d-B used in this reaction is not particularly limited as long as it is 1 equivalent or more relative to the compound represented by formula (2a-b), as long as the desired reaction proceeds. , usually 1 equivalent or more and 10 equivalents or less.

The transition metals used in this reaction are palladium, nickel, ruthenium, etc., and may have a ligand. Preferably, palladium acetate, [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride, tris(dibenzylideneacetone)dipalladium, tetrakis(triphenylphosphine)palladium, bis(triphenylphosphine)palladium dichloride, etc. Examples include palladiums.

The amount of transition metals used in this reaction is 0.001 equivalent or more and 1 equivalent or less relative to the compound represented by formula (2a-b), but is not particularly limited as long as the desired reaction proceeds. It never happens.

In order to make this reaction proceed efficiently, a phosphine ligand such as triphenylphosphine or tricyclohexylphosphine can be added.

The amount of 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 (2a-b), but is particularly limited as long as the desired reaction proceeds. It will not be done.

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

The amount of 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 (2a-b), as long as the desired reaction proceeds, but usually, It is 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, but includes water, ethers such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane. Examples include benzene-based solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene. These solvents can be used alone or in a mixture of two or more in any ratio.

The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but it is usually 3 times or more by weight or more and 200 times by weight relative to the compound represented by formula (2a-b). It is as follows.

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

As a post-treatment of the reaction, it is possible to perform a liquid separation operation by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, use an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, etc., an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, etc., or a saline solution. etc. can be used arbitrarily. During the separation operation, benzene solvents such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, 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, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. It is possible to add. Moreover, these solvents can be used alone or two or more kinds can be mixed in any ratio. The number of separations is not particularly limited and can be performed depending on the desired purity and yield. It is also possible to remove insoluble matter by performing a filtration operation, but this is not essential.

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

The reaction mixture containing the compound represented by formula (2a-d) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (2a-d) obtained after evaporation of the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. using an appropriate solvent. It may be set as appropriate depending on the desired purity.

式中、Ｒ４ｂは置換基Ａ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、Ｒ３、Ｒ４ａ、Ｒ５、Ｒ６ａ、ｎ、ｐおよびＸは前記と同義である。[Manufacturing method J]

In the formula, R4b represents a C2 to C6 alkynyl group or a C2 to C6 haloalkynyl group which may be optionally substituted with a substituent A, and R1, R2, R3, R4a, R5, R6a, n, p and X has the same meaning as above.

Production method J is a production intermediate represented by formula (2a), in which R4b is a C2 to C6 alkynyl group or a C2 to C6 haloalkynyl group, which may be optionally substituted with substituent A. A method for synthesizing a compound represented by 2a-e), which comprises reacting a compound represented by (2a-b) with a terminal alkyne compound in a solvent in the presence of a transition metal and a base. The manufacturing method includes obtaining by ring.

In formulas (2a-b), R4a 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 commercially available product or produced by a known method. Moreover, trimethylsilylacetylene can also be used as a terminal alkyne compound. In this case, it is necessary to introduce a trimethylsilylethynyl group into the compound represented by formula (2a-b) and then perform desilylation. Regarding 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). This can be done by referring 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 relative to the compound represented by formula (2a-b), as long as the desired reaction proceeds. Usually, it is 1 equivalent or more and 10 equivalents or less.

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

The amounts of transition metals used in this reaction should be 0.001 equivalent or more of palladium, etc. and copper, respectively, relative to the compound represented by formula (1a-b), so that the desired reaction proceeds. There are no particular restrictions as long as you do so. Preferred amounts for both are 0.001 equivalent or more and 1 equivalent or less.

Examples of the base used in this reaction include 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 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 (2a-b), as long as the desired reaction proceeds, but usually, It is 1 equivalent or more and 50 equivalents or less. Furthermore, liquid organic bases can be used as solvents.

In order to make this reaction proceed efficiently, a phosphine ligand such as tri-t-butylphosphine or 2-dicyclohexylphosphine-2'4'6'-triisopropylbiphenyl can be added, but it is not essential. do not have.

The amount of 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 (2a-b), but is particularly limited as long as the desired reaction proceeds. It will not be done.

The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds; Benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, nitrile solvents such as acetonitrile, N-methylpyrrolidone, N,N-dimethylformamide , amide solvents such as N,N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, halogen solvents such as dichloromethane, dichloroethane, chloroform, carbon tetrachloride, triethylamine, tributylamine, Examples include organic amine solvents such as isopropylamine, diethylamine, diisopropylamine, and diisopropylethylamine. These solvents can be used alone or in a mixture of two or more in any ratio.

The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but it is usually 3 times or more by weight or more and 200 times by weight relative to the compound represented by formula (2a-b). It is as follows.

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

As a post-treatment of the reaction, it is possible to perform a liquid separation operation by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, use an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, etc., an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, etc., or a saline solution. etc. can be used arbitrarily. During the separation operation, benzene solvents such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, 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, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. It is possible to add. Moreover, these solvents can be used alone or two or more kinds can be mixed in any ratio. The number of separations is not particularly limited and can be performed depending on the desired purity and yield. It is also possible to remove insoluble matter by performing a filtration operation, but this is not essential.

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

The reaction mixture containing the compound represented by formula (2a-e) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (2a-e) obtained after evaporation of the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. using an appropriate solvent. It may be set as appropriate depending on the desired purity.

式中、Ｒ２ｙとＲ３ｙは、それぞれ独立していて、フッ素原子、水酸基、シアノ基、ニトロ基、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、ＲｄＣ（＝Ｏ）－（ここで、Ｒｄは、前記と同義である。）、ＲｄＣ（＝Ｏ）Ｏ－（ここで、Ｒｄ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。）、ＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）、またはＲｅＣ（＝Ｏ）Ｎ（Ｒｆ）－（ここで、ＲｅおよびＲｆは、前記と同義である。）を表し、Ｒ３ｘはハロゲン原子を表し、ｌは０～３の整数（ｌが２以上の場合、２置換以上のＲ３ｙは、それぞれ独立した置換基を表す。）を表し、Ｊは酸素原子または硫黄原子を表し、Ｊが酸素原子の場合、Ｒ３ｂ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Ｃ３～Ｃ６のアルキニル基、またはＣ３～Ｃ６のハロアルキニル基を表し、Ｊが硫黄原子の場合、Ｒ３ｂ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、Ｑは水素原子または金属を表し、Ｒ１、Ｒ４Ａ、Ｒ５、Ｒ６ａ、ｐおよびＸは前記と同義である。[Manufacturing method K]

In the formula, R2y and R3y are each independently a fluorine atom, a hydroxyl group, a cyano group, a nitro group, a C1 to C6 alkyl group optionally substituted with a substituent C, a C1 to C6 haloalkyl group, a substituted C3 to C8 cycloalkyl group optionally substituted with group C, C2 to C6 alkenyl group optionally substituted with substituent C, C2 to C6 haloalkenyl group, optionally substituted with substituent C C2-C6 alkynyl group, C2-C6 haloalkynyl group, C1-C6 alkoxy group optionally substituted with substituent C, C1-C6 haloalkoxy group, optionally substituted with substituent C. a C3 to C8 cycloalkoxy group which may be optionally substituted with a C2 to C6 alkenyloxy group which may be optionally substituted with a substituent C, a C2 to C6 haloalkenyloxy group which may be optionally substituted with a substituent C alkynyloxy group, C3 to C6 haloalkynyloxy group, RdC(=O)-(herein, Rd has the same meaning as above), RdC(=O)O-(herein, Rd has the same meaning as above), ), Rc-L- (herein, Rc and L have the same meanings as above), RaRbN- (herein, Ra and Rb have the same meanings as above), or ReC( =O)N(Rf)- (where Re and Rf have the same meanings as above), R3x represents a halogen atom, l is an integer from 0 to 3 (when l is 2 or more, 2 Each of R3y above substitution represents an independent substituent.), J represents an oxygen atom or a sulfur atom, and when J is an oxygen atom, R3b is a C1 to C6 which may be optionally substituted with a substituent A. alkyl group, C1 to C6 haloalkyl group, C3 to C8 cycloalkyl group optionally substituted with substituent A, C2 to C6 alkenyl group optionally substituted with substituent A, C2 to C6 alkenyl group Represents a haloalkenyl group, a C3-C6 alkynyl group optionally substituted with substituent A, or a C3-C6 haloalkynyl group, and when J is a sulfur atom, R3b is a C1-C6 alkyl group or a C1-C6 alkyl group. represents a C6 haloalkyl group, Q represents a hydrogen atom or a metal, and R1, R4A, R5, R6a, p and X have the same meanings as above.

Production method K is a production intermediate represented by formula (2a), in which J represents an oxygen atom or a sulfur atom, and when J is an oxygen atom, R3b may be optionally substituted with a substituent C. C6 alkyl group, C1 to C6 haloalkyl group, C3 to C8 cycloalkyl group optionally substituted with substituent C, C2 to C6 alkenyl group optionally substituted with substituent C, C2 to C6 represents a haloalkenyl group, a C3 to C6 alkynyl group optionally substituted with a substituent C, or a C3 to C6 haloalkynyl group, and when J is a sulfur atom, R3b is a C1 to C6 alkyl group or a C1 to C6 alkyl group. - A method for synthesizing a compound represented by formula (2a-g) representing a C6 haloalkyl group, wherein the compound represented by formula (2a-f) and R3b-J-Q are combined in the presence of transition metals. Below is a manufacturing method including obtaining the compound by a coupling reaction in a solvent.

In the compounds represented by formulas (2a-f), R3x is preferably a chlorine atom, a bromine atom, or an iodine atom.

R3b-JQ used in this reaction can be obtained as a commercially available product or produced by a known method.

By using the compound represented by formula (2a-b) and R8c-J-Q in production method H in place of the compound represented by formula (2a-f) and R3b-J-Q, respectively. , Manufacturing method K can be carried out in accordance with manufacturing method H.

式中、Ｒ３ｃ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Ｃ２～Ｃ６のアルケニル基、またはＣ２～Ｃ６のハロアルケニル基を表し、Ｒ３ｃ－Ｂは有機ボロン酸類を表し、Ｒ１、Ｒ２ｙ、Ｒ３ｘ、Ｒ３ｙ、Ｒ４Ａ、Ｒ５、Ｒ６ａ、ｌ、ｐおよびＸは前記と同義である。[Manufacturing method L]

In the formula, R3c is a C1-C6 alkyl group optionally substituted with substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with substituent A, substituent A represents a C2 to C6 alkenyl group, or a C2 to C6 haloalkenyl group, which may be optionally substituted, R3c-B represents an organic boronic acid, R1, R2y, R3x, R3y, R4A, R5, R6a, l , p and X have the same meanings as above.

Production method L is a production intermediate represented by formula (2a), in which R3c is a C1 to C6 alkyl group which may be optionally substituted with a substituent A, a C1 to C6 haloalkyl group, or a C1 to C6 haloalkyl group, which is optionally substituted with a substituent A. Represented by formula (2a-h) which is an optionally substituted C3 to C8 cycloalkyl group, a C2 to C6 alkenyl group optionally substituted with substituent A, or a C2 to C6 haloalkenyl group A method for synthesizing a compound, comprising Suzuki-Miyaura coupling in which a compound represented by formula (2a-f) and an organic boronic acid (R3c-B) are reacted in a solvent in the presence of a transition metal and a base. This is a manufacturing method including obtaining by.

In the compounds represented by formulas (2a-f), R3x is preferably a chlorine atom, a bromine atom, or an iodine atom.

R3c-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 commercially available product or produced by a known method.

By using the compound represented by formula (2a-b) and R8d-B in manufacturing method I in place of the compound represented by formula (2a-f) and R3c-B, respectively, manufacturing method I Manufacturing method L can be carried out according to.

式中、Ｒ３ｄは置換基Ａ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、Ｒ２ｙ、Ｒ３ｘ、Ｒ３ｙ、Ｒ４Ａ、Ｒ５、Ｒ６ａ、ｌ、ｐおよびＸは前記と同義である。[Manufacturing method M]

In the formula, R3d represents a C2 to C6 alkynyl group or a C2 to C6 haloalkynyl group, which may be optionally substituted with a substituent A, and R1, R2y, R3x, R3y, R4A, R5, R6a, l, p and X have the same meanings as above.

Production method M is a production intermediate represented by formula (2a), in which R3d is a C2 to C6 alkynyl group, which may be optionally substituted with substituent A, or a C2 to C6 haloalkynyl group ( 2a-i) A method for synthesizing a compound represented by (2a-i), which comprises reacting a compound represented by (2a-f) with a terminal alkyne compound in a solvent in the presence of a transition metal and a base. The manufacturing method includes obtaining by ring.

In formulas (2a-f), R3x 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 commercially available product or produced by a known method. Moreover, trimethylsilylacetylene can also be used as a terminal alkyne compound. In this case, it is necessary to introduce a trimethylsilylethynyl group into the compound represented by formula (2a-f) and then perform desilylation. Regarding 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). This can be done by referring to non-patent literature such as .

By using the compound represented by formula (2a-b) in manufacturing method J in place of the compound represented by formula (2a-f), manufacturing method M can be carried out according to manufacturing method J. can.

式中、Ｒ５ｘは、水素原子、ハロゲン原子、シアノ基、ニトロ基、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、ＲｄＣ（＝Ｏ）－（ここで、Ｒｄは、前記と同義である。）、ＲｄＣ（＝Ｏ）Ｏ－（ここで、Ｒｄ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。）、ＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）、ＲｅＣ（＝Ｏ）Ｎ（Ｒｆ）－（ここで、ＲｅおよびＲｆは、前記と同義である。）、ＲｈＯＮ＝Ｃ（Ｒｉ）－（ここで、ＲｈおよびＲｉは、前記と同義である。）、または置換基Ｄで適宜０～５置換されてもよいフェニル基（ただし、２置換以上の置換基Ｄの場合、それぞれ独立している。）を表し、Ｒ５ｙはハロゲン原子を表し、Ｒ１、Ｒ２、Ｒ３、Ｒ４Ａ、ｎ、Ｘ、およびＨａｌＲは前記と同義である。[Manufacturing method N]

In the formula, R5x is a hydrogen atom, a halogen atom, a cyano group, a nitro group, a C1 to C6 alkyl group optionally substituted with substituent C, a C1 to C6 haloalkyl group, or a C1 to C6 haloalkyl group, optionally substituted with substituent C. a C3-C8 cycloalkyl group, 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; group, C2 to C6 haloalkynyl group, C1 to C6 alkoxy group optionally substituted with substituent C, C1 to C6 haloalkoxy group, C3 to C8 cyclo optionally substituted with 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- C6 haloalkynyloxy group, RdC(=O)-(herein, Rd has the same meaning as above), RdC(=O)O-(herein, Rd has the same meaning as above), Rc-L- (here, Rc and L have the same meanings as above), RaRbN- (here, Ra and Rb have the same meanings as above), ReC(=O)N(Rf)- (Here, Re and Rf have the same meanings as above.), RhON=C(Ri)- (Here, Rh and Ri have the same meanings as above.), or the substituent D is 0 to 5 as appropriate. represents an optionally substituted phenyl group (however, in the case of two or more substituents D, each is independent), R5y represents a halogen atom, R1, R2, R3, R4A, n, X, and HalR has the same meaning as above.

Manufacturing method N is a manufacturing method for obtaining compounds represented by formulas (2a-k) among the manufacturing intermediates represented by formula (2a), and is a manufacturing method for obtaining compounds represented by formulas (2a-j) and This production method includes reacting a halogenating agent (HalR) in a solvent in the presence of a base.

Bases used in this reaction include metal hydrides such as sodium hydride, organolithiums such as methyllithium, butyllithium, sec-butyllithium, t-butyllithium, hexyllithium, lithium diisopropylamide, hexamethyldisilazane lithium. , sodium hexamethyldisilazane, potassium hexamethyldisilazane, and other metal amides.

The amount of base used in this reaction may be 1 equivalent or more relative to the compound represented by formula (2a-j), and is not particularly limited as long as the desired reaction proceeds, but usually , 1 equivalent or more and 10 equivalents or less.

The halogenating agents used in this reaction include selectrofluor (N-fluoro-N'-triethylenediamine bis(tetrafluoroborate)), N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, ,3-dichloro-5,5-dimethylhydantoin, 1,3-dibromo-5,5-dimethylhydantoin, 1,3-diiodo-5,5-dimethylhydantoin, bromine, iodine, hexachloroethane, 1,2-dibromo -1,1,2,2-tetrachloroethane and the like.

The amount of 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 (2a-j), as long as the desired reaction proceeds. Usually, 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 equivalent or more and the desired reaction proceeds, and is usually 1 equivalent or more and 5 equivalents or less.

The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds; Examples include benzene-based solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene, and hydrocarbon-based solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. These solvents can be used alone or in a mixture of two or more in any ratio.

The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but it is usually 3 times or more by weight or more and 200 times by weight relative to the compound represented by formula (2a-j). It is as follows.

The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually -80°C to 100°C or below the boiling point of the solvent.

As a post-treatment of the reaction, it is possible to perform a liquid separation operation by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, use an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, etc., an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc., thiosulfuric acid, etc. An aqueous solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved, or a saline solution can be arbitrarily used. During the separation operation, benzene solvents such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, 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, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. It is possible to add. Moreover, these solvents can be used alone or two or more kinds can be mixed in any ratio. The number of separations is not particularly limited and can be performed depending on the desired purity and yield.

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

The reaction mixture containing the compound represented by formula (2a-k) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (2a-k) obtained after evaporation of the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. using an appropriate solvent. It may be set as appropriate depending on the desired purity.

式中、Ｒ９はＣ１～Ｃ６のアルキル基を表し、Ｒ１、Ｒ２、Ｒ３、Ｒ４Ａ、Ｒ５ｘ、ｎ、およびＸは前記と同義である。[Manufacturing method O]

In the formula, R9 represents a C1 to C6 alkyl group, and R1, R2, R3, R4A, R5x, n, and X are as defined above.

Production method O is a production method for obtaining a compound represented by formula (2a-l) among the production intermediates represented by formula (2a), and is a production method for obtaining a compound represented by formula (2a-l) and a compound represented by formula (2a-j). This is a manufacturing method including reacting a compound represented by formula (7) in a solvent in the presence of a base.

Bases used in this reaction include metal hydrides such as sodium hydride, organolithiums such as methyllithium, butyllithium, sec-butyllithium, t-butyllithium, hexyllithium, lithium diisopropylamide, hexamethyldisilazane lithium. , sodium hexamethyldisilazane, potassium hexamethyldisilazane, and other metal amides.

The amount of base used in this reaction may be 1 equivalent or more relative to the compound represented by formula (2a-j), and is not particularly limited as long as the desired reaction proceeds, but usually , 1 equivalent or more and 10 equivalents or less.

The compound represented by formula (7) used in this reaction can be obtained as a commercially available product or can be produced by a known method. Preferred R9 is a methyl group or an ethyl group.

The amount of the compound represented by formula (7) used in this reaction is not particularly limited as long as it is 1 equivalent or more relative to the compound represented by formula (2a-j), as long as the desired reaction proceeds. However, it is usually 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; Examples include benzene-based solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene, and hydrocarbon-based solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. These solvents can be used alone or in a mixture of two or more in any ratio.

The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but it is usually 3 times or more by weight or more and 200 times by weight relative to the compound represented by formula (2a-j). It is as follows.

The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually -80°C to 100°C or below the boiling point of the solvent.

As a post-treatment of the reaction, it is possible to perform a liquid separation operation by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, use an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, etc., an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc., thiosulfuric acid, etc. An aqueous solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved, or a saline solution can be arbitrarily used. During the separation operation, benzene solvents such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, 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, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. It is possible to add. Moreover, these solvents can be used alone or two or more kinds can be mixed in any ratio. The number of separations is not particularly limited and can be performed depending on the desired purity and yield.

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

The reaction mixture containing the compound represented by formula (2a-l) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (2a-l) obtained after evaporation of the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. using an appropriate solvent. It may be set as appropriate depending on the desired purity.

式中、Ｒ１、Ｒ２、Ｒ３、Ｒ４Ａ、Ｒ５、ｍ、ｎ、Ｘおよび破線部は前記と同義である。[Manufacturing method P]

In the formula, R1, R2, R3, R4A, R5, m, n, X and the broken line part have the same meanings as above.

Production method P is a method for synthesizing a compound represented by formula (2d) among the production intermediates represented by formula (2), in which the compound represented by formula (2c) and a reducing agent are This is a manufacturing method that involves reacting in a solvent.

Reducing agents used in this reaction include combinations of hydrogen, metals such as palladium, cobalt and nickel, acids, and metals such as tin, zinc and iron, and are particularly limited as long as the desired reaction proceeds. However, here we will explain the combination of acid and iron.

The amount of iron used in this reaction may be 3 equivalents or more relative to the compound represented by formula (2c), and is not particularly limited as long as the desired reaction proceeds; however, it is usually 3 equivalents or more. The amount is equal to or more than 50 equivalents.

Examples of acids used in this reaction include inorganic acids such as hydrochloric acid and ammonium chloride.
The amount of acid used in this reaction may be at least a catalytic amount with respect to the compound represented by formula (2c), and is not particularly limited as long as the desired reaction proceeds; however, it is usually 0. .01 equivalent or more and 20 equivalents or less.

The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, and examples thereof include water solvents and alcoholic solvents such as methanol, ethanol, and isopropanol. These solvents can be used alone or in a mixture of two or more in any ratio.

The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but it is usually 3 times or more and 200 times or less by weight relative to the compound represented by formula (2c). be.

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

As a post-treatment of the reaction, it is possible to perform a liquid separation operation by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, use an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, etc., an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc., thiosulfuric acid, etc. An aqueous solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved, or a saline solution can be arbitrarily used. During the separation operation, benzene solvents such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, 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, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. It is possible to add. Moreover, these solvents can be used alone or two or more kinds can be mixed in any ratio. The number of separations is not particularly limited and can be performed depending on the desired purity and yield. It is also possible to remove insoluble matter by performing a filtration operation, but this is not essential.

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

The reaction mixture containing the compound represented by formula (2d) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (2d) obtained after evaporation of the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. using an appropriate solvent. It may be set as appropriate depending on the desired purity.

式中、Ｒ１、Ｒ２、Ｒ３、Ｒ４Ａ、Ｒ５、ｎ、ｍ、Ｘおよび破線部は前記と同義である。[Manufacturing method Q]

In the formula, R1, R2, R3, R4A, R5, n, m, X and the broken line part have the same meanings as above.

Production method Q is a method for obtaining a compound represented by formula (1), which is a compound of the present invention, in which the compound represented by formula (2d) and nitrites are reacted in a solvent, and then a reducing agent is added. This is a production method that involves a Sandmeyer reaction.

Examples of the nitrites used in this reaction include nitrite metal salts such as sodium nitrite, and nitrite esters such as isoamyl nitrite and t-butyl nitrite.

The amount of nitrous acids used in this reaction is not particularly limited as long as it is 1 equivalent or more relative to the compound represented by formula (2d), as long as the desired reaction proceeds, but usually, The amount is 1 equivalent or more and 10 equivalents or less.

Examples of the reducing agent used in this reaction include hypophosphorous acid.
The amount of the reducing 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 (2d), as long as the desired reaction proceeds.

The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but includes water, ethers such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane. alcoholic solvents such as methanol, ethanol, isopropanol, benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, nitrile solvents such as acetonitrile, N-methylpyrrolidone, N,N-dimethylformamide , amide solvents such as N,N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, halogen solvents such as dichloromethane, dichloroethane, chloroform, carbon tetrachloride, dimethyl sulfoxide, sulfolane, etc. Examples include sulfur-based solvents. These solvents can be used alone or in a mixture of two or more in any ratio.

The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but it is usually 3 times or more and 200 times or less by weight relative to the compound represented by formula (2d). 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 -20°C to 150°C or below the boiling point of the solvent.

As a post-treatment of the reaction, it is possible to perform a liquid separation operation by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, use an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, etc., an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc., thiosulfuric acid, etc. An aqueous solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved, or a saline solution can be arbitrarily used. During the separation operation, benzene solvents such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, 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, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. It is possible to add. Moreover, these solvents can be used alone or two or more kinds can be mixed in any ratio. The number of separations is not particularly limited and can be performed depending on the desired purity and yield. It is also possible to remove insoluble matter by performing a filtration operation, but this is not essential.

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

The reaction mixture containing the compound represented by formula (2d) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (2d) obtained after evaporation of the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. using an appropriate solvent. It may be set as appropriate depending on the desired purity.

（式中、ｍは、１～２の整数（ｍが２の場合、２置換のＲ５は、それぞれ独立している。）を表し、Ｒ１、Ｒ２、Ｒ３、Ｒ４Ａ、Ｒ５、Ｒ６、ｎ、Ｘおよび破線部は、式（１）と同義である。）で表される化合物は、本発明の式（１）で表される化合物を得る有用な製造中間体となりうる。According to production methods P and Q, a compound represented by formula (2c) and a compound represented by formula (2d), that is, formula (2)

(In the formula, m represents an integer of 1 to 2 (when m is 2, each of the two substituted R5s is independent), R1, R2, R3, R4A, R5, R6, n, and the broken line portion have the same meaning as formula (1).) The compound represented by formula (1) can be a useful production intermediate for obtaining the compound represented by formula (1) of the present invention.

を表す。Specific examples of the production intermediate represented by formula (2) are combinations of structural formulas I-1 to I-32 shown in Table 5 and structural formulas Ph (Ph-1 to Ph-302) shown in Table 2. Represented by In addition, R5, R6, m, X and the broken line part in Table 5 have the same meaning as formula (2), and Ph has the following partial structure

represents.

These compounds are for illustrative purposes only, and the production intermediate of the present invention is not limited thereto.

式中、Ｒｊは水素原子またはＣ１～Ｃ６のアルキル基を表し、ｑは０～１の整数を表し、Ｒ１、Ｒ２、Ｒ３、ｎ、Ｒ４Ａ、Ｒ５、Ｘおよび破線部は前記と同義である。[Manufacturing method R]

In the formula, Rj represents a hydrogen atom or a C1 to C6 alkyl group, q represents an integer of 0 to 1, and R1, R2, R3, n, R4A, R5, X and the broken line portion have the same meanings as above.

Production method R is a method for synthesizing a compound represented by formula (1-b) among compounds represented by formula (1), which comprises a compound represented by formula (1-a) and a diazophosphonate. This is a manufacturing method that includes reacting a reagent with a reagent in a solvent in the presence of a base.

Examples of the diazophosphonate reagent used in this reaction include dimethyl (1-diazo-2-oxypropyl)phosphonate and dimethyl (diazomethyl)phosphonate.

The amount of the diazophosphonate reagent used in this reaction is not particularly limited as long as it is 1 equivalent or more relative to the compound represented by formula (1-a), and as long as the desired reaction proceeds. is usually 1 equivalent or more and 10 equivalents or less.

The bases used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, sodium hydride, sodium methoxide, sodium ethoxide, sodium t-butoxide, potassium t- These include metal alkoxides such as butoxide.

The amount of 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 (1-a), and as long as the desired reaction proceeds, but usually , 1 equivalent or more and 20 equivalents or less.

The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds; Examples include alcohol solvents such as methanol, ethanol, and isopropanol. These solvents can be used alone or in a mixture of two or more in any ratio.

The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but it is usually 3 times or more by weight or more and 200 times by weight relative to the compound represented by formula (1-a). It is as follows.

The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but it is usually -20° C. or higher and 100° C. or lower or lower than the boiling point of the solvent.

As a post-treatment of the reaction, it is possible to perform a liquid separation operation by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, use an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, etc., an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc., thiosulfuric acid, etc. An aqueous solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved, or a saline solution can be arbitrarily used. During the separation operation, benzene solvents such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, 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, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. It is possible to add. Moreover, these solvents can be used alone or two or more kinds can be mixed in any ratio. The number of separations is not particularly limited and can be performed depending on the desired purity and yield.

The reaction mixture containing the compound represented by formula (1-b) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (1-b) obtained after evaporation of the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. using an appropriate solvent. It may be set as appropriate depending on the desired purity.

式中、Ｒｋは水素原子またはＣ１～Ｃ６のアルキル基を表し、Ｒ１、Ｒ２、Ｒ３、Ｒ４Ａ、Ｒ５、Ｒｊ、ｎ、ｑ、Ｘおよび破線部は前記と同義である。なお、式中の波線は幾何異性を表し、Ｅ体またはＺ体のどちらか一方のみ、あるいはＥ体とＺ体との任意の割合の混合物である。[Manufacturing method S]

In the formula, Rk represents a hydrogen atom or a C1 to C6 alkyl group, and R1, R2, R3, R4A, R5, Rj, n, q, X and the broken line part have the same meanings as above. Note that the wavy line in the formula represents geometric isomerism, and is either only the E form or the Z form, or a mixture of the E form and the Z form in any ratio.

Production method S is a method for synthesizing a compound represented by formula (1-c) among compounds represented by formula (1), which comprises a compound represented by formula (1-a), RkONH ₂ and This is a manufacturing method that includes reacting in a solvent.

RkONH ₂ used in this reaction is available as a commercial product or can be produced by a known method. RkONH ₂ may be a salt formed with an acidic compound such as hydrochloric acid or sulfuric acid, and can be used in the presence of a base in the reaction system. Examples of the bases used 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. However, there are no particular limitations as long as the desired reaction proceeds. The amount of the base to be used may be 1 equivalent or more relative to RkONH ₂ and is not particularly limited as long as the desired reaction proceeds, but it is usually 1 equivalent or more and 20 equivalents or less. It is also possible to use RkONH ₂ after desalting it in advance by a known method.

The amount of RkONH ₂ used in this reaction is not particularly limited as long as it is 1 equivalent or more relative to the compound represented by formula (1-a), but as long as the desired reaction proceeds, it is usually , 1 equivalent or more and 20 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, isopropanol, benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, 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, dichloromethane, dichloroethane, chloroform, carbon tetrachloride Examples include halogen-based solvents such as. These solvents can be used alone or in a mixture of two or more in any ratio.

The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but it is usually 3 times or more by weight or more and 200 times by weight relative to the compound represented by formula (1-a). It is as follows.

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

As a post-treatment of the reaction, it is possible to perform a liquid separation operation by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, use an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, etc., an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc., thiosulfuric acid, etc. An aqueous solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved, or a saline solution can be arbitrarily used. During the separation operation, benzene solvents such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, 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, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. It is possible to add. Moreover, these solvents can be used alone or two or more kinds can be mixed in any ratio. The number of separations is not particularly limited and can be performed depending on the desired purity and yield.

Moisture can be removed from the reaction mixture containing the compound represented by formula (1-c) obtained above using a desiccant such as sodium sulfate or magnesium sulfate, but this is not essential.

The reaction mixture containing the compound represented by formula (1-c) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (1-c) obtained after evaporation of the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. using an appropriate solvent. It may be set as appropriate depending on the desired purity.

式中、Ｒｌ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、またはＣ３～Ｃ８のシクロアルキル基を表し、Ｒ１、Ｒ２、Ｒ３、Ｒ４Ａ、Ｒ５、ｎ、ｑ、Ｘおよび破線部は前記と同義である。[Manufacturing method T]

In the formula, Rl represents a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, or a C3 to C8 cycloalkyl group, which may be optionally substituted with a substituent B, and R1, R2, R3, R4A, R5, n, q, X and the broken line portion have the same meanings as above.

Production method T is a method for synthesizing a compound represented by formula (1-e) among compounds represented by formula (1), which comprises a compound represented by formula (1-d) and an organometallic reagent. This is a manufacturing method that includes reacting these in a solvent.

The organometallic reagents used in this reaction include organomagnesium halide (Rl-Mg-Hal: where Hal represents a halogen atom and Rl has the same meaning as above), organolithium reagent (Rl-Li: Here, Rl has the same meaning as above), organomagnesium halide-zinc (II) ate complex reagent ([(Rl) ₃ -Zn] ^- [Mg-Hal] ⁺ [Mg-(Hal) ₂ ] ₂ : Here, Rl and Hal have the same meanings as above. These organometallic reagents can be obtained as commercially available products or manufactured by known methods.

The amount of the organometallic reagent used in this reaction is not particularly limited as long as the amount of the organometallic reagent used in this reaction is 1 equivalent or more relative to the formula (1-d), and as long as the desired reaction proceeds. is usually 1 equivalent or more and 10 equivalents or less.

The solvent used in the reaction is not particularly limited as long as the desired reaction proceeds, but includes ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane, and hexane. , heptane, cyclohexane, methylcyclohexane, and other hydrocarbon solvents. These solvents can be used alone or in a mixture of two or more in any ratio.

The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but it is usually 3 times or more by weight or more and 200 times by weight relative to the compound represented by formula (1-d). It is as follows.

The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually -80°C to 100°C or below the boiling point of the solvent.

As a post-treatment of the reaction, it is possible to perform a liquid separation operation by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, use an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, etc., an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc., thiosulfuric acid, etc. An aqueous solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved, or a saline solution can be arbitrarily used. During the separation operation, benzene solvents such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, diethyl ether, diisopropyl ether, methyl- It is possible to add solvents that are incompatible 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. It is possible. Moreover, these solvents can be used alone or two or more kinds can be mixed in any ratio. The number of separations is not particularly limited and can be performed depending on the desired purity and yield.

Moisture can be removed from the reaction mixture containing the compound represented by formula (1-e) obtained above using a desiccant such as sodium sulfate or magnesium sulfate, but this is not essential.

The reaction mixture containing the compound represented by formula (1-e) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (1-e) obtained after evaporation of the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. using an appropriate solvent. It may be set as appropriate depending on the desired purity.

式中、ＲｍおよびＲｎは、それぞれ独立していて、水素原子またはＣ１～Ｃ４のアルキル基（ただし、ＲｍとＲｎの炭素数の総和は４個以下である。）を表し、Ｒ１、Ｒ２、Ｒ３、Ｒ４Ａ、Ｒ５、ｎ、ｑ、Ｘおよび破線部は前記と同義である。[Manufacturing method U]

In the formula, Rm and Rn each independently represent a hydrogen atom or a C1 to C4 alkyl group (however, the total number of carbon atoms of Rm and Rn is 4 or less), and R1, R2, R3 , R4A, R5, n, q, X and the broken line portion have the same meanings as above.

Production method U is a method for synthesizing a compound represented by formula (1-g) among compounds represented by formula (1), in which a compound represented by formula (1-f) is synthesized in the presence of an acid. Below is a manufacturing method including reaction in a solvent.

Examples of 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 is no particular restriction as long as the desired reaction proceeds.

The amount of acid used in this reaction may be a catalytic amount and is not particularly limited as long as the desired reaction proceeds; .01 equivalent or more. Furthermore, 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, but includes aqueous solvents, acidic solvents such as acetic acid and methanesulfonic acid, diethyl ether, diisopropyl ether, methyl-t- 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. Examples include urea-based solvents, dichloromethane, dichloroethane, chloroform, and halogen-based solvents such as carbon tetrachloride. These solvents can be used alone or in a mixture of two or more in any ratio.

The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but it is usually 3 times or more by weight or more and 200 times by weight relative to the compound represented by formula (1-f). It is as follows.

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

As a post-treatment of the reaction, a liquid separation operation can be performed by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, use an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, etc., an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc., thiosulfuric acid, etc. An aqueous solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved, or a saline solution can be arbitrarily used. During the separation operation, benzene solvents such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, 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, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. It is possible to add. Moreover, these solvents can be used alone or two or more kinds can be mixed in any ratio. The number of separations is not particularly limited and can be performed depending on the desired purity and yield.

Moisture can be removed from the reaction mixture containing the compound represented by formula (1-g) obtained above using a desiccant such as sodium sulfate or magnesium sulfate, but this is not essential.

The reaction mixture containing the compound represented by formula (1-g) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (1-g) obtained after evaporation of the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. using an appropriate solvent. It may be set as appropriate depending on the desired purity.

式中、ＲｘはＣ１～Ｃ６のアルキル基またはベンジル基を表し、Ｒ１０は水素原子またはメトキシ基を表し、Ｒ１、Ｒ２、Ｒ３、Ｒ４Ａ、ｎ、Ｘおよび破線部は前記と同義である。[Manufacturing method V]

In the formula, Rx represents a C1 to C6 alkyl group or a benzyl group, R10 represents a hydrogen atom or a methoxy group, and R1, R2, R3, R4A, n, X and the broken line part have the same meanings as above.

Production method V is a method for synthesizing a production intermediate represented by formula (1-i), in which a compound represented by formula (1-h) and a compound represented by formula (8) are combined with a base. This is a manufacturing method that includes reacting in the presence of a solvent.

The compound represented by formula (1-h) used in this reaction can be synthesized according to Reference Example.

The compound represented by formula (8) used in this reaction can be obtained as a commercially available product or can be produced by a known method.

The amount of the compound represented by formula (8) used in this reaction is particularly limited as long as it is 1 equivalent or more relative to the compound represented by formula (1-h), as long as the desired reaction proceeds. Although not always used, it is usually 1 equivalent or more and 20 equivalents or less.

Bases used in this reaction include metal hydrides such as sodium hydride, inorganic bases such as sodium carbonate, potassium carbonate, and cesium carbonate, sodium methoxide, sodium ethoxide, sodium t-butoxide, potassium t-butoxide, etc. Examples include metal alkoxides and metal amides such as lithium diisopropylamide, lithium hexamethyldisilazane, sodium hexamethyldisilazane, and potassium hexamethyldisilazane.

The amount of 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 (1-h), as long as the desired reaction proceeds, but usually, It is 1 equivalent or more and 20 equivalents or less.

The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds; Examples include amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide and N,N-dimethylacetamide, and urea solvents such as 1,3-dimethyl-2-imidazolidinone. These solvents can be used alone or in a mixture of two or more in any ratio.

The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but it is usually 3 times or more by weight or more and 200 times by weight relative to the compound represented by formula (1-h). It is as follows.

The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but it is usually -80°C or higher and 150°C or lower or lower than the boiling point of the solvent.

As a post-treatment of the reaction, it is possible to perform a liquid separation operation by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, use an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, etc., an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc., thiosulfuric acid, etc. An aqueous solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved, or a saline solution can be arbitrarily used. During the separation operation, benzene solvents such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, 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, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. It is possible to add. Moreover, these solvents can be used alone or two or more kinds can be mixed in any ratio. The number of separations is not particularly limited and can be performed depending on the desired purity and yield.

Moisture can be removed from the reaction mixture containing the compound represented by formula (1-i) obtained above using a desiccant such as sodium sulfate or magnesium sulfate, but this is not essential.

The reaction mixture containing the compound represented by formula (1-i) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (1-i) obtained after evaporation of the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. using an appropriate solvent. It may be set as appropriate depending on the desired purity.

式中、Ｒ１、Ｒ２、Ｒ３、Ｒ４Ａ、Ｒ５、Ｒ５ｘ、Ｒｘ、ｎ、Ｘおよび破線部は前記と同義である。[Manufacturing method W]

In the formula, R1, R2, R3, R4A, R5, R5x, Rx, n, X and the broken line part have the same meanings as above.

Production method W is a method for synthesizing a compound represented by formula (1-j) among compounds represented by formula (1), in which a compound represented by formula (1-i) and formula (9) are synthesized. ) in a solvent in the presence of an acid.

（式中、ＲｙはＣ１～Ｃ６のアルキル基を表し、ｎｂは１～４の整数を表し、Ｒ５およびＲ５ｘは前記と同義である。）で表される反応等価体を含む。さらに、Ｒ５ｘが水素原子を表す場合には、

（式中、ＲｙａはＣ１～Ｃ６のアルキル基を表し、Ｒ５、Ｒｙおよびｎｂは前記と同義である。式中の波線は幾何異性を表し、Ｅ体またはＺ体のどちらか一方のみ、あるいはＥ体とＺ体との任意の割合の混合物である。）を含む。In the compound represented by formula (1-i), Rx is preferably a t-butoxy group.
The compound represented by formula (9) used in this reaction can be obtained as a commercially available product or can be produced by a known method. Moreover, the compound represented by formula (9) is

(In the formula, Ry represents a C1 to C6 alkyl group, nb represents an integer of 1 to 4, and R5 and R5x have the same meanings as above.) Furthermore, when R5x represents a hydrogen atom,

(In the formula, Rya represents a C1 to C6 alkyl group, and R5, Ry, and nb have the same meanings as above. The wavy line in the formula represents geometric isomerism, and only one of the E form or Z form, or the E It is a mixture of Z-isomer and Z-isomer in any proportion.)

The amount of the compound represented by formula (9) used in this reaction is not particularly limited as long as the amount of the compound represented by formula (9) is 1 equivalent or more relative to the compound represented by formula (1-i), as long as the desired reaction proceeds. However, it is usually 1 equivalent or more and 10 equivalents or less.

Examples of acids 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, and there is no particular limitation as long as the desired reaction proceeds. .

The amount of acid used in this reaction is not particularly limited as long as it is a catalytic amount relative to the compound represented by formula (1-i), and as long as the desired reaction proceeds, but usually, It is 1 equivalent or more and 20 equivalents or less.

The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds; Examples include alcohol solvents such as methanol, ethanol, and isopropanol. These solvents can be used alone or in a mixture of two or more in any ratio.

The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but it is usually 3 times or more by weight or more and 200 times by weight relative to the compound represented by formula (1-i). It is as follows.

The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but it is usually -80°C or higher and 150°C or lower or lower than the boiling point of the solvent.

As a post-treatment of the reaction, it is possible to perform a liquid separation operation by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, use an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, etc., an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc., thiosulfuric acid, etc. An aqueous solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved, or a saline solution can be arbitrarily used. During the separation operation, benzene solvents such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, 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, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. It is possible to add. Moreover, these solvents can be used alone or two or more kinds can be mixed in any ratio. The number of separations is not particularly limited and can be performed depending on the desired purity and yield.

Moisture can be removed from the reaction mixture containing the compound represented by formula (1-j) obtained above using a desiccant such as sodium sulfate or magnesium sulfate, but this is not essential.

The reaction mixture containing the compound represented by formula (1-j) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (1-j) obtained after evaporation of the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. using an appropriate solvent. It may be set as appropriate depending on 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 X]

In the formula, La represents S, Lb represents SO or _SO2 , and Ox' represents an oxidizing agent.

_Production method A method for synthesizing a compound represented by formula (La) in which La contained in R1, R2, R3, R4 and R5 is S among the compounds represented by formula (1) and formula (2); This is a manufacturing method that includes reacting an oxidizing agent (Ox') in a solvent.

Examples of the oxidizing agent used in this reaction include peroxides such as hydrogen peroxide solution and meta-chloroperbenzoic acid. It is also possible to add transition metals such as sodium tungstate.

The amount of oxidizing agent used in this reaction is usually 1.0 equivalent or more and 1.2 equivalent or less relative to the compound represented by formula (La) when producing _SO2 . When doing so, the amount is usually 2 equivalents or more and 10 equivalents or less. Further, when adding transition metals, the amount 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, but includes water, acidic solvents such as acetic acid, benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, etc. 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 alone or in a mixture of two or more in any ratio.

The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but it is usually 3 times or more and 200 times or less by weight relative to the compound represented by formula (La). 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 -10° C. or higher and 120° C. or lower or lower than the boiling point of the solvent.

As a post-treatment of the reaction, it is possible to perform a liquid separation operation by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, use an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, etc., an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc., thiosulfuric acid, etc. An aqueous solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved, or a saline solution can be arbitrarily used. During the separation operation, benzene solvents such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, 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, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. It is possible to add. Moreover, these solvents can be used alone or two or more kinds can be mixed in any ratio. The number of separations is not particularly limited and can be performed depending on the desired purity and yield.

Moisture can be removed from the reaction mixture containing the compound represented by formula (Lb) obtained above using a desiccant such as sodium sulfate or magnesium sulfate, but this is not essential.

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

The reaction mixture containing the compound represented by formula (Lb) obtained after evaporation of the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. using an appropriate solvent. It may be set as appropriate depending on the desired purity.

The compound represented by formula (1) can be produced by arbitrarily combining the production methods A to X shown above. Alternatively, the compound represented by formula (1) can be produced by arbitrarily combining known methods and production methods A to X.

Since the compound of the present invention can control organisms harmful to plants, it can be used as a pesticide, particularly as a pest control agent for agriculture and horticulture. Specific examples include fungicides, insecticides, herbicides, plant growth regulators, and the like. Preferably it is a bactericide.

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

Plant diseases as used in the present invention refer to systemic abnormal pathological symptoms such as wilting, damping, yellowing, atrophy, elongation, or spots, leaf blight, mosaic, etc. on crops, flowers, flowering plants, trees, etc. , causing localized pathological symptoms such as leaf curls, withered branches, root rot, root galls, and galls. In other words, plants become diseased. Pathogens that cause plant diseases include mainly fungi, bacteria, spiroplasma, phytoplasma, viruses, viroids, parasitic higher plants, nematodes, and the like. The compounds of the present invention are effective against fungi, but are not limited thereto.

Diseases caused by fungi are mainly fungal diseases. Examples of fungi (pathogens) that cause fungal diseases include Neclinoid fungi, oomycetes, zygomycetes, ascomycetes, basidiomycetes, and deuteromycetes. For example, the fungi include clubroot fungi, potato powdery fungi, sugar beet root fungi, the oomycetes include Phytophthora blight, downy mildew, Pythium spp., and Aphanomyces spp., and the zygomycetes include Rhizopus spp. Fungi include peach leaf curl fungus, corn sesame leaf blight fungus, rice blast fungus, powdery mildew fungus, anthracnose fungus, Fusarium head fungus, Bakanae fungus, Sclerotinia fungus, and basidiomycetes include rust fungi, smut fungus, and purple spot fungi. Examples of the feather blight fungus, blast fungus, sheath blight fungus, and Deuteromycetes include botrytis fungi, Alternaria genus fungi, Fusarium genus fungi, Penicillium genus fungi, Rhizoctonia genus fungi, and white silk fungi.

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), Thanatephorus cucumeris, Ceratobasidium setariae, Waitea circinata, and brown sheath blight (Thana tephorus cucumeris), coccoid sclerotia ( Sclerotium hydrophilum), Wairea circinata, Entyloma dactylidis, Magnaporthe salvinii, Ceratobasidium c. ornigerum), sesame leaf blight (Cochliobolus miyabeanus), row leaf blight Blight (Sphaerulina oryzina), Gibberella fujikuroi, Seedling blight (Pythium spp., Fusarium spp., Trichoderma spp., Rhizopus spp., R hizoctonia solani, Mucor sp., Phoma sp.), seedling rot diseases (Pythium spp., Achlya spp., Dictyuchus spp.), rice mildew (Claviceps virens), black smut (Tilletia barclayana), brown rice (Curvularia spp., Alterna) ria spp.), yellowing disease (Sclerophthora macrospora ), Xanthomonas oryzae pv. oryzae, Acidovorax avenae subsp. avenae, Erwinia ananas, Burkholderia blight plantarii), Burkholderia glumae ), leaf sheath browning disease (Pseudomonas fuscovaginae), leaf blight (Pseudomonas syringae pv. oryzae), stock rot (Erwinia chrysanthemi), yellow wilt (Phytoplasma oryzae) ae), Rice stripe tenuivirus, Rice stripe blight ( rice dwarf reovirus);
Powdery mildew (Blumeria graminis f.sp.hordei; f.sp.tritici), rust (Puccinia striiformis, Puccinia graminis, Puccinia recondita, Puc) of wheat cinia hordei), spotted leaf disease (Pyrenophora graminea), web spot disease ( Pyrenophora teres), Gibberella zeae, Fusarium culmorum, Fusarium avenaceum, Monographella nivalis, snow rot (Typhula incarna) ta, Typhula ishikariensis, Monographella nivalis), naked smut (Ustilago nuda), slug smut (Tilletia caries, Tilletia controversa), Pseudocercosporella herpotrichoides, Ceratobasidium gramineum, Rhynchosporium secalis, Septoria tritici, Phaeosphaeria nodorum, Fusarium spp. ., Pythium spp., Rhizoctonia spp., Septoria spp., Pyrenophora spp.), damping-off (Gaeumannomyces graminis), anthracnose (Colletotrichum grami) nicola), ergot disease (Claviceps purpurea), spot disease (Cochliobolus sativus), black knot disease (Pseudomonas syringae pv. syringae);
Fusarium head blight (Gibberella zeae, etc.), seedling damping-off (Fusarium avenaceum, Penicillium spp, Pythium spp., Rhizoctonia spp.), and rust (Puccinia spp.) of corn ), sesame leaf blight (Cochliobolus heterostrophus), smut ( Ustilago maydis), anthrax (Colletotrichum graminicola), northern spot disease (Cochliobolus carbonum), brown streak disease (Acidovorax avenae subsp. avenae), streak bacterial disease ( Burkholderia andropogonis), bacterial lodging disease (Erwinia chrysanthemi pv. zeae), Bacterial wilt (Erwinia stewartii); Grape downy mildew (Plasmopara viticola), Rust (Physopella ampelopsidis), Powdery mildew (Uncinula necator), Black rot (Elsinoe am.) pelina), late rot (Glomerella cingulata, Colletotrichum) acutatum), black rot (Guignardia bidwellii), vine split disease (Phomopsis viticola), soot spot disease (Zygophiala jamaicensis), gray mold (Botrytis cinerea), bud blight ( Diaporthe medusaea), Helicobasidium mompa ), Rosellinia necatrix, Agrobacterium vitis; apple powdery mildew (Podosphaera leucotricha), Venturia inaequalis, leaf spot ( Alternaria mali), Akaboshi disease ( Gymnosporangium yamadae), Monilinia mali, Valsa ceratosperma, Botryosphaeria berengeriana, Colletotric hum acutatum, Glomerella cingulata), sooty spot disease (Zygophiala jamaicensis), sooty spot disease (Gloeodes pomigena) ), Mycosphaerella pomi, Helicobasidium mompa, Rosellinia necatrix, Phomopsis mali, Diaporthe tanakae, Phomopsis mali, Diaporthe tanakae (Diplocarpon mali), apple fire blight (Erwinia amylovora), Agrobacterium tumefaciens, Agrobacterium rhizogenes;
Pear black spot (Alternaria kikuchiana), black spot (Venturia nashicola), red spot (Gymnosporangium asiaticum), ring spot (Botryosphaeria berengeriana f.sp. piricola), Phomopsis fukushii, and bacterial branch blight (Phomopsis fukushii). Erwinia sp.), Agrobacterium tumefaciens, Erwinia chrysanthemi pv. chrysanthemi, Pseudomonas syringae pv. phytophthora blight (Phytophthora cactorum, Phytophthora syringae), bacterial branch blight (Erwinia sp.); peach scab (Cladosporium carpophilum), homopsis rot (Phomopsis sp.), late blight (Phytophthora sp.), anthracnose (Colletotrich) um gloeosporioides), leaf curl disease (Taphrina deformans), borer bacterial disease (Xhanthomonas campestris pv. pruni), tumefaciens disease (Agrobacterium tumefaciens); cherry anthracnose disease (Glomerella cingulata), juvenile fungi Monilinia kusanoi, Monilinia fructicola ), Agrobacterium tumefaciens, Pseudomonas syringae pv. kaki; Mycosphaerella nawae), powdery mildew (Phyllactinia kakikora) , Agrobacterium tumefaciens; citrus black spot (Diaporthe citri), green mold (Penicillium digitatum), blue mold (Penicillium italicum), scab disease (El sinoe fawcettii), brown rot (Phytophthora citrophthora ), canker disease (Xhanthomonas campestris pv. citri), Pseudomonas syringae pv. syringae, Greening disease (Liberibactor asiaticus), Agrobacterium tumefaciens;
Botrytis cinerea on tomatoes, cucumbers, beans, strawberries, potatoes, cabbage, eggplants, lettuce, etc.; Sclerotinia sclerotiorum on tomatoes, cucumbers, beans, strawberries, potatoes, rapeseed, cabbage, eggplants, lettuce, etc. ); Seedling damping-off of tomatoes, cucumbers, beans, radish, watermelon, eggplant, rapeseed, green pepper, spinach, sugar beet, etc. (Rhizoctonia spp., Pythium spp., Fusarium spp., Phythophthora spp., Sclerotinia spp. clerotiorum etc.) Ralstonia solanacearum; downy mildew of cucurbits (Pseudoperonospora cubensis), powdery mildew (Sphaerotheca fuliginea), anthracnose (Colletotrichum o) bryoniae), vine blight (Didimella bryoniae), vine split disease (Fusarium oxysporum), Phytophthora parasitica, Phytophthora melonis, Phytophthora nicotianae, Phytophthora drechsleri, Phytophthora phthora capsici etc.), bacterial brown spot disease (Xhanthomonas campestris pv. cucurbitae), soft rot disease (Erwinia carotovora subsp. carotovora), bacterial spot disease ( Pseudomonas syringae pv. lachrymans), Pseudomonas marginalis pv. marginalis, Streptomyces sp., Agrobacterium rhizogenes), Cucumber mosaic virus;
Tomato rot (Alternaria solani), leaf mold (Fulvia fulva), late blight (Phytophthora infestans), wilt (Fusarium oxysporum), root rot (Pythium myriotylum, P. ythium dissotocum), anthrax (Colletotrichum gloeosporioides), canker sores Clavibacter michiganensis, Pseudomonas corrugata, Pseudomonas viridiflava, Erwinia carotovora subsp. otovora), leaf club disease (Crynebacterium sp.), yellow chlorosis (Phytoplasma asteris) , Tobacco leaf curl subgroup III geminivirus; powdery mildew of eggplant (Sphaerotheca fuliginea, etc.), sooty mold (Mycovellosiella nattrassii), late blight ( Phytophthora infestans), brown rot (Phytophthora capsici), brown spot bacteria Pseudomonas cichorii, Pseudomonas corrugata, Erwinia chrysanthemi, Erwinia carotovora subsp. carotovora , bacterial spot (Pseudomonas sp.); black spot of rapeseed ( Alternaria brassicae), black rot (Xhanthomonas campestris pv. campestris), black spot bacterial disease (Pseudomonas syringae pv. maculicola), soft rot (Erwinia c. arotovora); black spot disease of cruciferous vegetables (Alternaria brassicae, etc.), white spot disease ( Cercosporella brassicae), root rot (Phoma lingam), clubroot (Plasmodiophora brassicae), downy mildew (Peronospora parasitica), black rot (Xhanthomonas ca) campestris), Pseudomonas syringae pv. maculicola), soft rot (Erwinia carotovora subsp. carotovora);
Cabbage stump rot (Thanatephorus cucumeris), yellowing disease (Fusarium oxysporum), black soot rot (Alternaria brassisicola); Chinese cabbage end rot (Rhizoctonia solani), yellowing disease (Ve) rticillium dahliae); allium rust (Puccinia allii); ), Alternaria porri, Sclerotium rolfsii, Phytophthora porri, Sclerotium cepivorum; Curtobacterium onion flaccumfaciens), soft rot (Erwinia carotovora subsp. carotovora), Pseudomonas syringae pv. syringae, Erwinia rhapontici, Burkholderia gladioli, Phytoplasma asteris); soft rot of garlic (Erwinia carotovora subsp. carotovora), spring rot (Pseudomonas marginalis pv. marginalis); soybean purpura (Cercospora kikuchii), black cabbage (Elsinoe glycines), black spot (Diaporthe phaseolorum), rhizoctobe Rhizoctonia solani, Phytophthora sojae, Downy mildew (Peronospora manshurica), rust (Phakopsora pachyrhizi), anthracnose (Colletotrichum truncatum, etc.), leaf blight (Xhanthomonas campestris pv. glycinea), bacterial spot disease (Pseudomonas syringae pv. glycinea); anthracnose of kidney beans ( Ralstonia solanacearum, Pseudomonas syringae pv. phaseolicola, Pseudomonas v. iridiflava), leaf blight (Xhanthomonas campestris pv. phaseoli);
Groundnut blight (Mycosphaerella berkeleyi), brown spot (Mycosphaerella arachidis), bacterial wilt (Ralstonia solanacearum); pea powdery mildew (Erysiphe pisi), downy mildew (P. ronospora pisi), Pseudomonas blight (Pseudomonas syringae pv. pisi), vine rot bacterial disease (Xhanthomonas campestris pv. pisi); downy mildew of broad bean (Peronospora viciae), late blight (Phytophthora nicotianae); summer blight of potato (A alternaria solani), black bruise (Thanatephorus cucumeris) , Phytophthora infestans, Helminthosporium solani, Fusarium oxysporum, Fusarium solani, Spongospora subter ranea), bacterial wilt (Ralstonia solanacearum), black foot blight (Erwinia carotovora) subsp. atroseptica), Streptomyces scabies, Streptomyces acidiscabies, Erwinia carotovora subsp. carotovora, sticky rot (Cr ostridium spp.), ring rot (Clavibacter michiganensis subsp. sepedonicus); damping off of sweet potatoes Diseases (Streptomyces ipomoeae); Sugar beet brown spot (Cercospora beticola), downy mildew (Peronospora schachtii), black root disease (Aphanomyces cochioides), snake's eye disease (Phoma be tae), Agrobacterium tumefaciens, so Streptomyces scabies, Pseudomonas syringae pv. aptata;
Carrot black leaf blight (Alternaria dauci), clubroot (Rhizobacter dauci), tumefaciens (Agrobacterium tumefaciens), Streptomyces spp., soft rot (Erwi) nia carotovora subsp. carotovora); Strawberry powdery mildew (Sphaerotheca aphanis var. aphanis), late blight (Phytophthora nicotianae, etc.), anthracnose (Glomerella cingulata, etc.), fruit rot disease (Pythium ultimum) ), bacterial wilt (Ralstonia solanacearum), bacterial horn spot disease (Xhanthomonas campestris), bacterial shoot blight (Pseudomonas marginalis pv. marginalis); tea net blast (Exobasidium reticulatum), white star disease (Elsinoe leucospila), anthracnose (Col letotrichum theae-sinensis), Pestalotiopsis longiseta, red Pseudomonas syringae pv. theae, canker disease (Xhanthomonas campestris pv. theicola), Pseudomonas sp. nata), powdery mildew (Erysiphe cichoracearum), anthrax (Colletotrichum) gloeosporioides), late blight (Phytophthora nicotianae), wildfire disease (Pseudomonas syringae pv. tabaci), yellow bacterium disease (Pseudomonas syringae pv. mellea), cavities disease (Erwinia carotovora subsp. carotovora), damping-off disease (Ralstonia solanacearum), Tobacco mosaic virus;
Coffee rust (Hemileia vastatrix); banana blight (Mycosphaerella fijiensis), Panama blight (Fusarium oxysporum f.sp cubense); cotton damping-off (Fusarium oxys) porum), white mold (Ramularia areola); Sclerotinia sclerotiorum, Xhanthomonas campestris pv. malvacearum, Erwinia carotovora subsp. carotovora, bacterial spot disease (P seudomonas syringae pv.helianthi); rose scab (Diplocarpon rosae), udon Phytophthora megasperma, downy mildew (Peronospora sparsa), Agrobacterium tumefaciens; chrysanthemum brown spot (Se) ptoria obesa), white rust (Puccinia horiana) , Phytophthora cactorum, Pseudomonas cichorii, Erwinia carotovora subsp. carotovora, Agrobacterium tumefacillus aciens), hair root disease (Agrobacterium rhizogenes), greening disease (Phytoplasma aurantifolia); Lawn brown patch disease (Rhizoctonia solani), dollar spot disease (Sclerotinia homoeocarpa), Curvularia sp., rust (Puccinia zoysiae), Helminthosporium leaf blight (Cochliob) olus sp.), cloud disease (Rhynchosporium secalis), damping-off (Gaeumannomyces graminis), anthracnose (Colletotrichum sp.), snow rot brown small-grain sclerotia (Typhula incarnata), snow rot black small-grain sclerotia (Typhu) la ishikariensis), snow rot large sclerotia disease (Myriosclerotinia borealis), fairy ring disease (Marasmius oreades, etc.), pythium disease (Pythium aphanidermatum, etc.), rice blast disease (Pyricularia grisea), and the like.

Although the compound of the present invention may be used alone, it is preferably mixed with a solid carrier, liquid carrier, gas carrier, surfactant, sticking agent, dispersant, stabilizer, etc., and is used as a powder or wettable powder. It can be used as a composition such as a wettable powder, a water-dispersible powder, a water-soluble powder, a granule, an emulsion, a liquid, a microemulsion, an aqueous suspension, an aqueous emulsion, or a suspoemulsion. The composition is not limited to these compositions as long as the effect is exhibited.

Specific formulation examples are shown below, but the formulation is not limited thereto.

[Formulation example 1 flowable agent]
Compound of the present invention (10 parts by mass), sodium salt of formaldehyde condensate of naphthalene sulfonic 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 then wet-pulverized using glass beads with a diameter of 1.0 mm in a Dyno Mill 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 this solution to obtain an emulsion.

[Formulation Example 3 Hydrating agent]
Compound of the present invention (10 parts by mass), white carbon (10 parts by mass), polyvinyl alcohol (2 parts by mass), dioctyl sulfosuccinate sodium salt (0.5 parts by mass), alkylbenzenesulfonic acid sodium salt (5 parts by mass), calcination Diatomaceous earth (10 parts by mass) and kaolinite clay (62.5 parts by mass) are thoroughly mixed and ground with an air mill to obtain a wettable powder.

Application of the composition (agricultural and horticultural pest control agent, agricultural and horticultural fungicide, etc.) containing the compound of the present invention will be explained below.

Methods for applying the composition containing the compound of the present invention include a method in which it is brought into contact with plants or seeds, or a method in which it is contained in cultivation soil and brought into contact with roots or rhizomes of plants. Specific examples include foliage spraying of the composition on individual plants, injection treatment, seedling box treatment, cell tray treatment, spraying treatment on plant seeds, smearing treatment on plant seeds, immersion treatment on plant seeds, and treatment on plant seeds. powder coating treatment, spraying treatment on the soil surface, soil mixing after spraying on the soil surface, injection treatment into the soil, soil mixing after injection treatment in the soil, soil irrigation treatment, soil irrigation treatment after soil irrigation treatment. Examples include soil mixing. Generally, any method of application available to those skilled in the art will be sufficiently effective.

A "plant" as used in the present invention refers to a plant that photosynthesizes and lives without exercise. Specific examples include rice, wheat, barley, corn, coffee, bananas, grapes, apples, pears, peaches, cherry blossoms, persimmons, citrus, soybeans, green beans, cotton, strawberries, potatoes, cabbage, lettuce, tomatoes, cucumbers, eggplants, Examples include watermelon, sugar beet, spinach, snow pea, pumpkin, sugarcane, tobacco, green pepper, sweet potato, taro, konnyaku, cotton, sunflower, rose, tulip, chrysanthemum, 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, such as soybeans, corn, cotton, etc. that are resistant to herbicides, and rice adapted to cold regions. , tobacco, etc., and agricultural and horticultural crops such as corn and cotton that have been given the ability to produce insecticidal substances. Further examples include trees such as pine, ash, ginkgo, maple, oak, poplar, and zelkova. Furthermore, the term "plant" as used in the present invention is a general term for all parts constituting the above-mentioned individual plant, and includes, for example, stems, leaves, roots, seeds, flowers, fruits, and the like.

The term "seed" as used in the present invention refers to a seed that stores nutrients for germination of young plants and is used for agricultural propagation. Specific examples include seeds of corn, soybeans, cotton, rice, sugar beets, wheat, barley, sunflowers, tomatoes, cucumbers, eggplants, spinach, snow peas, pumpkins, sugarcane, tobacco, green peppers, oilseed rape, etc., 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 rakkyo, and seeds and tubers of genetically modified crops.

The amount and concentration of the composition containing the compound of the present invention will vary depending on the target crop, the target disease, the degree of disease occurrence, the dosage form of the compound, the method of application, and various environmental conditions. The appropriate amount of active ingredient is 0.1 to 10,000 g per hectare, preferably 10 to 1,000 g per hectare. Further, in the case of seed treatment, the amount of active ingredient used is 0.0001 to 1000 g per kg of seeds, preferably 0.001 to 100 g. When a composition containing the compound of the present invention is used as a foliar spray treatment on individual plants, a spray treatment on the soil surface, an injection treatment into the soil, or a soil irrigation treatment, it is diluted in an appropriate carrier at an appropriate concentration. After that, processing may be performed. When a composition containing the compound of the present invention is brought into contact with plant seeds, the composition may be diluted to an appropriate concentration and then used by dipping, coating, spraying, or smearing on the plant seeds. The amount of the composition to be used when dipping, dusting, spraying or smearing is usually about 0.05 to 50%, preferably 0.1 to 30%, of the weight of dry plant seeds as the amount of active ingredients. However, it may be set as appropriate depending on the form of the composition and the type of plant seeds to be treated, and is not limited to these ranges.

The compound of the present invention may be used with other agricultural chemicals, such as fungicides, insecticides (including acaricides and nematicides), herbicides, microbial materials, plant growth regulators, and nucleic acids, as necessary. It can be used in combination with a disease control agent (International Publication No. 2014/062775), a soil conditioner, or a fertilizer substance as an active ingredient. Methods for using the compound of the present invention and other agricultural chemicals in combination include methods in which the compound of the present invention and other agricultural chemicals are formulated into one dosage form, and methods in which the compound of the invention and other agricultural chemicals are formulated into one dosage form, and both methods are used in which the compounds of the invention and other agricultural chemicals are formulated into separate dosage forms. Mix the two before use, use both at the same time in separate dosage forms, or use either one of the two in separate dosage forms. One method is to use the other after

Specific components contained in the fungicide that can be used in combination with the compound of the present invention are exemplified by the following group b, including salts, isomers, and N-oxides thereof. However, known disinfectants are not limited to these.

Group b:
b-1: Phenylamide fungicide As a phenylamide fungicide, [b-1.1]: benalaxyl, [b-1.2] benalaxyl M or kiralaxyl, [b -1.3] furaxyl, [b-1.4] metalaxyl, [b-1.5] metalaxyl-M or mefenoxam, [b-1.6] oxadixyl ( oxadixyl), [b-1.7]ofurace, and the like.

b-2: Mitotic and cell division inhibitors As mitotic and cell division 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] phenamacryl, 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] dimoxyst Dimoxystrobin, [b-4.4] enoxastrobin, [b-4.5] famoxadone, [b-4.6] fenamidone, [b-4.7] ] phenaminestrobin, [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 picoxystrobin, [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)
Examples of quinone internal inhibitors (QiI agents) include [b-5.1] cyazofamid, [b-5.2] amisulbrom, and the like.

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

b-7: Quinone external stigmatellin binding subsite inhibitor (QoSI agent)
[b-7.1] ametoctradin and the like are exemplified as quinone external stigmatellin binding subsite inhibitors (QoSI agents).

b-8: Amino acid biosynthesis inhibitor As an amino acid biosynthesis inhibitor, [b-8.1] cyprodinil, [b-8.2] mepanipyrim, [b-8.3] pyrimethanil. ) etc.

b-9: Protein biosynthesis inhibitor As the protein biosynthesis inhibitor, [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 As the signal transduction inhibitor, [b-10.1] fenpiclonil, [b-10.2] fludioxonil, [b-10.3] quinoxyfen, [b-10.4] proquinazid, [b-10.5] chlozolinate, [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 inhibitors As lipid and cell membrane biosynthesis inhibitors, [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] Examples include echlomezol or etridiazole, [b-11.12] iodocarb, [b-11.13] propamocarb, and [b-11.14] prothiocarb.

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 (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] ipfentriflu conazole ) etc.

b-13: Amine-based fungicide As the amine-based fungicide, [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 ) etc.

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 inhibitor 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] mandipropamide, [b-17.9] valifenalate, and the like.

b-17: Melanin biosynthesis inhibitor As a melanin biosynthesis inhibitor, [b-17.1] phthalide or fthalide, [b-17.2] pyroquilone, [b-17.3] tricyclazole. (tricyclazole), [b-17.4] carpropamide, [b-17.5] diclocymet, [b-17.6] fenoxanil, [b-17.7] tolprocarb ) etc.

b-18: Host plant resistance inducer As host plant resistance inducer, [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 As a dithiocarbamate fungicide, [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 Examples of phthalimide-based fungicides include [b-20.1] captan, [b-20.2] captafol, and [b-20.3] folpet. ), [b-20.4] fluorofolpet, and the like.

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

b-22: Multi-point contact-active fungicide As a multi-point contact-activated fungicide, [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] dodecylbenzene sulfone Dodecylbenzenesulfonic acid bisethylenediamine copper [II] salt, DBEDC, [b-22.6] sulfur, [b-22.7] fluorimide (f luoroid), [b-22. 8] chlorothalonil, [b-22.9] dichlofluanid, [b-22.10] tolylfluanid, [b-22.11] anilazine, [b- 22.12] dithianon, [b-22.13] chinomethionat or quinomethionate, [b-22.14] extract from cotyledons of lentil seedlings (BLAD), and the like.

b-23: Other fungicides Other fungicides include [b-23.1] dichlobentiazox, [b-23.2] fenpicoxamide, [b-23.3] ] Dipymethitrone, [b-23.4] bupirimate, [b-23.5] dimethirimol, [b-23.6] ethirimol, [b-23.7] acetic acid fentin acetate, [b-23.8] fentin chloride, [b-23.9] fentin hydroxide, [b-23.10] oxolinic acid (oxolinic acid), [b-23.11] hymexazol, [b-23.12] octilinone, [b-23.13] fosetyl, [b-23.14] hymexazol phosphorous acid, [b-23.15] sodium phosphorous acid, [b-23.16] ammonium phosphorous acid, [b-23.17] phosphorous acid; Potassium phosphite, [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,

で表される化合物（国際公開第９８／０４６６０７号参照）、[b-23.37] Formula (s1)

A compound represented by (see WO 98/046607),

で表される化合物（国際公開第０８／１４８５７０号参照）、[b-23.38] Formula (s2)

A compound represented by (see WO 08/148570),

で表される化合物（国際公開第９２／０１２９７０号参照）、[b-23.39] Formula (s3)

A compound represented by (see WO 92/012970),

で表される化合物（国際公開第１２／０８４８１２号参照）、[b-23.40] Formula (s4)

A compound represented by (see WO 12/084812),

で表される化合物（ｇｏｕｇｅｒｏｔｉｎ）、[b-23.41] Formula (s5)

A compound represented by (gougerotin),

で表される化合物（ｎｉｎｇｎａｎｍｙｃｉｎ）、[b-23.42] Formula (s6)

A compound represented by (ningnanmycin),

で表される化合物（国際公開第１０／１３６４７５号参照）、[b-23.43] Formula (s7)

A compound represented by (see WO 10/136475),

で表される化合物（国際公開第１４／０１０７３７号参照）、[b-23.44] Formula (s8)

A compound represented by (see WO 14/010737),

で表される化合物（国際公開第１１／０８５０８４号参照）、[b-23.45] Formula (s9)

A compound represented by (see WO 11/085084),

で表される化合物（国際公開第１１／１３７００２号参照）、[b-23.46] Formula (s10)

A compound represented by (see WO 11/137002),

で表される化合物（国際公開第１３／１６２０７２号参照）、[b-23.47] Formula (s11)

A compound represented by (see WO 13/162072),

で表される化合物（国際公開第０８／１１０３１３号参照）、[b-23.48] Formula (s12)

A compound represented by (see WO 08/110313),

で表される化合物（国際公開第０９／１５６０９８号参照）、[b-23.49] Formula (s13)

A compound represented by (see WO 09/156098),

で表される化合物（国際公開第１２／０２５５５７号参照）、[b-23.50] Formula (s14)

A compound represented by (see WO 12/025557),

で表される化合物（国際公開第１４／００６９４５号参照）、[b-23.51] Formula (s15)

A compound represented by (see WO 14/006945),

［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-23.52] Formula (s16)

[In the formula, A3 represents a hydrogen atom, a halogen atom, a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, or a cyano group, and A4 represents a hydrogen atom, a C1 to C6 alkyl group, a C1 to C6 alkyl group, or a C1 to C6 alkyl group. Represents a haloalkyl group or a C3 to C8 cycloalkyl group. ] (see WO 14/095675),

［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、国際公開第０９／１３７６５１号参照）、[b-23.53] Formula (s17)

[In the formula, 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 to C6 alkoxy group, and when m1 is 2 or more, 2 or more A7's each represent an independent substituent and may be the same or different. ] Compounds represented by (see WO 09/137538 and WO 09/137651),

［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-23.54] Formula (s18)

[In the formula, 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 to C6 alkyl group, and A13 represents a halogen atom or a C1 to C6 alkyl group. , represents a halogen atom, a cyano group, a C1 to C6 alkyl group, or a C1 to C6 alkoxy group. ] (see WO 12/031061),

［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-23.55] Formula (s19)

[In the formula, m2 represents an integer of 0 to 6, A14 and A15 each independently represent a halogen atom, a cyano group, or a C1 to C6 alkyl group, and A16 is a hydrogen atom, a halogen atom , or represents a C1 to C6 alkoxy group, A17 represents a halogen atom or a C1 to C6 alkoxy group, and when m2 is 2 or more, 2 or more A17s each represent an independent substituent, and are the same or It's okay to be different. ] (see WO 05/121104),

［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-23.56] Formula (s20)

[In the formula, A18 and A19 are each independently a halogen atom, a cyano group, or a C1 to C6 alkyl group, and A20, A21 and A22 are each independently a hydrogen atom, a halogen atom, Or represents a C1 to C6 alkoxy group. ] (see WO 07/066601),

［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、国際公開第０９／０１６２２０号、国際公開第１０／１３０７６７号参照）、[b-23.57] Formula (s21)

[In the formula, A23 and A24 each independently represent a hydrogen atom, a halogen atom, a C1 to C6 alkyl group, or a C3 to C8 cycloalkyl group, and X represents an oxygen atom or a sulfur atom. ] Compounds represented by (see WO 07/087906, WO 09/016220, WO 10/130767),

［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-23.58] 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 to C8 cycloalkyl group, and when m3 is 2 or more, two or more A25's each represent an independent substituent and may be the same or different. ] (see WO 13/092224),

［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-23.59] 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),

［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-23.60] Formula (s24) or formula (s25)

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

［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-23.61] Formula (s26) or formula (s27)

[In the formula, m5 represents an integer of 0 to 5, A30 represents a C1 to C6 alkyl group, and A31 is a halogen atom, a cyano group, a C1 to C6 alkyl group, or a C1 to C6 haloalkyl group. and when m5 is 2 or more, 2 or more A31s each represent an independent substituent and 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 a C6 alkynyl group. ] (see WO 13/037717),

［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、国際公開第１０／０６９８８２号参照）、[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. ] Compounds represented by (see WO 06/031631 and WO 10/069882),

［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-23.63] Formula (s29)

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

［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-23.64] Formula (s30)

[In the formula, A41 represents a hydrogen atom, a hydrosulfur group (-SH), a thiocyanate group (-SCN), or a C1 to C6 alkylthio group, and A42, A43, A44 and A45 are each independently , hydrogen atom, or halogen atom. ] (see International Publication No. 09/077443),

［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-23.65] 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),

［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-23.66] 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).

Specific components contained in the insecticide that can be used in combination with the compound of the present invention are exemplified by the following group c, including salts, isomers, and N-oxides thereof. However, known insecticides are not limited to these.

Group c:
c-1: Carbamate-based acetylcholinesterase (AChE) inhibitor Carbamate-based acetylcholinesterase (AChE) inhibitors include [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] furathiocarb, [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 etc.

c-2: Organophosphate acetylcholinesterase (AChE) inhibitor As an organophosphate acetylcholinesterase (AChE) inhibitor, [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] diclofenthion, [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-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, [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, [c-2 .64] trichlorfon, [c-2.65] vamidothion, [c-2.66] chlorothion, [c-2.67] 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] etrimphos ( etrimfos), [c-2.80] oxydeprofos, [c-2.81] formothion, [c-2.82] fensulfothion, [c-2.83] isazofos ( isazofos), [c-2.84] imicyafos, [c-2.85] isamidofos, [c-2.86] thionazin, [c-2.87] fosthietan etc.

c-3: GABAergic chloride channel blocker GABAergic chloride channel blocker includes [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 Examples include acetoprole.

c-4: Sodium channel modulator Sodium channel modulators include [c-4.1] acrinathrin, [c-4.2] 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] theta -cypermethrin (theta-cypermethrin), [c-4.17]zeta-cypermethrin, [c-4.18]cyphenothrin [(1R)-trans-isomer] (cyphenothrin [(1R) -trans-isomer]), [c-4.19] deltamethrin, [c-4.20] 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, [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-methofluthrin, [c-4.33] momfluorothrin, [c-4.34] epsilon-momfluorothrin, [ c-4.35] permethrin, [c-4.36] phenothrin [(1R)-trans-isomer], [c-4.37] pralethrin ( 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], [c-4.44]tralomethrin , [c-4.45]transfluthrin, [c-4.46]ZXI8901(3-(4-bromophenoxy)phenyl]-cyanomethyl 4-(difluoromethoxy)-α-(1-methylethyl )benzeneacetate) , [c-4.47] biopermethrin, [c-4.48] furamethrin, [c-4.49] profluthrin, [c-4.50] flubrocitrinate ( flubrocythrinate), [c-4.51] dimefluthrin, [c-4.52] DDT (dichloro-diphenyl-trichloroethane), [c-4.53] methoxychlor, [c-4.54] Examples include phenothrin, [c-4.55] fluvalinate, and the like.

c-5: Nicotinic acetylcholine receptor (nAChR) competitive modulator As nicotinic acetylcholine receptor (nAChR) competitive modulator, [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, Examples include [c-5.11] flupyradifurone, [c-5.12] triflumezopyrim, and the like.

c-6: Nicotinic acetylcholine receptor (nAChR) allosteric modulator As a nicotinic acetylcholine receptor (nAChR) allosteric modulator, [c-6.1] spinosad, [c-6.2] spinetoram, etc. can be mentioned.

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

c-8: Juvenile hormone analogues Juvenile hormone analogues include [c-8.1] hydroprene, [c-8.2] kinoprene, and [c-8.3] methoprene. ), [c-8.4]phenoxycarb, [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] borax 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 salt, and the like.

c-10: Chord tone organ TRPV channel modulator Examples of the chord tone organ TRPV channel modulator include [c-10.1] pymetrozine, [c-10.2] pyrifluquinazone, and the like.

c-11: Amite growth inhibitor As a mite growth inhibitor, [c-11.1] clofentezine, [c-11.2] diflobidazin, [c-11.3] hexythiazox. (hexythiazox), [c-11.4]ethoxazole, and the like.

c-12: Mitochondrial ATP synthase inhibitor Mitochondrial ATP synthase inhibitors include [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, etc. .

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

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

c-15: Chitin biosynthesis inhibitor type 0
Chitin biosynthesis inhibitor type 0 includes [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
Examples of chitin biosynthesis inhibitor type 1 include [c-16.1]buprofezin.

c-17: Inhibitor of molting of insects of the order Hymenoptera [c-17.1] Cyromazine and the like can be mentioned as inhibitors of molting of insects of the order Hydera.

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

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

c-20: Mitochondrial electron transport chain complex III inhibitor Mitochondrial electron transport chain complex III inhibitors include [c-20.1] hydramethylnon, [c-20.2] acequinocyl, Examples include [c-20.3] fluacrypyrim, [c-20.4] bifenazate, and the like.

c-21: Mitochondrial electron transport chain complex I inhibitor (METI)
Mitochondrial electron transport chain complex I inhibitors (METI) include [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, etc. It will be done.

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

c-23: Acetyl CoA carboxylase inhibitor As the acetyl CoA carboxylase inhibitor, [c-23.1] spirodiclofen, [c-23.2] spiromesifen, [c-23.3] ] Spirotetramat and the like.

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

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

c-26: Ryanodine receptor modulator As the ryanodine receptor modulator, [c-26.1] chlorantraniliprole, [c-26.2] cyantraniliprole, [c-26. 3] flubendiamide and the like.

c-27: Chord-tone organ modulator with unspecified target site Examples of chordo-tone organ modulators with unspecified target site include [c-27.1] flonicamid.

c-28: Other insecticides Other insecticides include [c-28.1] azadirachtin, [c-28.2] benzoximate, and [c-28.3] phenysobromo. phenisobromolate, [c-28.4] chinomethionat, [c-28.5] dicofol, [c-28.6] pyridalyl, [c-28.7] bromopropyl 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] polynactins, [c-28.21] sabadilla, [c-28.22] sulcofuron salt (sulcofuron- 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] barium polysulfide, [c-28.33] bencrothiaz, [c-28.3] 4 ]5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-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, [c-28.39] camphechlor, [c-28.40] chlorbenside, [c-28.41] chlordecone, [c-28.42] chlordimeform, [c-28.43] chlorphene chlorfenethol, [c-28.44] chlorfenson, [c-28.45] fluazuron, [c-28.46] metaldehyde, [c-28.47] ] bialaphos, [c-28.48] levamisole 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] Chlorobenzilate, [c-28.56] flufenzine, [c-28.57] benzomate, [c-28.58] flufenerim, [c-28.59] albendazole, [c-28.60] oxibendazole, [c-28.61] fenbendazole, [c-28.62] metam-sodium, [c-28.63] 1,3-dichloropropene, [c-28.64] flometoquin, [c-28.65] cyclaniliprole, [c -28.66] tetraniliprole, [c-28.67] broflanilide, [c-28.68] dichloromezothiaz, [c-28.69] ethylene dibromide ( ethylene dibromide), [c-28.70] acrylonitrile, [c-28.71] bis(2-chloroethyl) ether, [c-28.72] 1-bromo -2-chloroethane (1-bromo-2-chloroethane), [c-28.73] 3-bromo-1-chloroprop-1-ene (3-bromo-1-chloroprop-1-ene), [c-28 .74] bromocyclen, [c-28.75] 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, [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] hydroxypropyl starch, [c-28.93] Fatty acid glyceride (decanoyloctanoylglycerol), [c-28.94] propylene glycol monofatty acid ester, [c-28.95] diatomite, [c -28 .96] afoxolaner, [c-28.97] fluazindolizine, [c-28.98] afidopyropen, [c-28.99] cyhalodiamide , [c- 28.100] thioxazafene, [c-28.101] fluhexafon, [c-28.102] fluralaner, [c-28.103] fluxametamide, [c- 28.104] tetrachlorantraniliprole, [c-28.105] sarolaner, [c-28.106] lotilaner, [c-28.107] cycloxapr id), [c-28.108] 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-dicarboximide), [c-28.116] Bayer 22408 (O,O-diethyl O-naphthalimido phosphorothioate), [c-28.117 ] Bayer 32394 (tris(1-dodecyl-3-methyl-2-phenylbenzimidazolium)hexacyanoferrate),

で表される化合物（国際公開第１０／０５１９２６号参照）、[c-28.118] Formula (s34)

A compound represented by (see WO 10/051926),

で表される化合物（国際公開第１３／１１５３９１号参照）、[c-28.119] Formula (s35)

A compound represented by (see WO 13/115391),

で表される化合物（国際公開第１２／０２９６７２号参照）、[c-28.120] Formula (s36)

A compound represented by (see WO 12/029672),

で表される化合物（国際公開第０６／０５６１０８号参照）、[c-28.121] Formula (s37)

A compound represented by (see WO 06/056108),

で表される化合物（国際公開第１４／０５３４５０号、国際公開第１５／１４４６８３号参照）、[c-28.122] Formula (s38)

A compound represented by (see WO 14/053450, WO 15/144683),

で表される化合物（国際公開第１４／０５３４５０号、国際公開第１５／１４４６８３号参照）、[c-28.123] Formula (s39)

A compound represented by (see WO 14/053450, WO 15/144683),

で表される化合物（国際公開第１４／０５３４５０号、国際公開第１５／１４４６８３号参照）、[c-28.124] Formula (s40)

A compound represented by (see WO 14/053450, WO 15/144683),

［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-28.125] Formula (s41)

[In the formula, m6 represents an integer from 0 to 2. ] (see WO 10/129497),

［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-28.126] Formula (s42)

[In the formula, m7 represents an integer from 0 to 2. ] (see WO 11/152320),

［式中、ｍ８は、０～２の整数を表す。］で表される化合物（特開２０１５―１６０８１３号公報参照）、[c-28.127] Formula (s43)

[In the formula, m8 represents an integer from 0 to 2. ] (see JP-A No. 2015-160813 ),

［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、国際公開第１４／００５９８２号参照）、[c-28.128] Formula (s44)

[In the formula, A52 represents a hydrogen atom or a fluorine atom. ] (see International Publication No. 11/134964, International Publication No. 14/005982),

［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-28.129] 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),

［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-28.130] 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 International Publication No. 11/134964, International Publication No. 14/005982),

［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-28.131] 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 International Publication No. 09/049851),

［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-28.132] Formula (s48)

[In the formula, A57 represents a hydrogen atom, a fluorine atom, or a chlorine atom, and A58 is

represents one type of partial structure selected from the group consisting of. ] (see WO 11/067272),

［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-28.133] Formula (s49)

[In the formula, A59 represents a hydrogen atom, a fluorine atom, or a chlorine atom, and A60 is

represents a substructure selected from the group consisting of ] (see WO 10/090344),

［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-28.134] Formula (s50)

[In the formula, m10 represents an integer of 0 to 2, A61 represents a trifluoromethyl group, a trifluoromethylthio group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group, and A62 represents a hydrogen atom, or It 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),

［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、国際公開第１６／１４４３５１号、国際公開第１６／１４４６７８号参照）、[c-28.135] Formula (s51)

[In the formula, A63 represents a hydrogen atom or a fluorine atom, the amide group is bonded to the 4th or 5th position, and A64 is

represents a substructure selected from the group consisting of ] Compounds represented by (see WO 15/038503, WO 16/144351, WO 16/144678),

［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、国際公開第１６／０１６３６９号参照）、[c-28.136] Formula (s52)

[In the formula, A65 represents a hydrogen atom, a C1 to C6 alkyl group, or a C1 to C6 haloalkyl group, A66 represents a hydrogen atom, a halogen atom, or a C1 to C6 alkyl group, and A67 and A68 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 to 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. ] Compounds represented by (see WO 12/143317 and WO 16/016369),

［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、国際公開第１６／０５５４３１号参照）、[c-28.137] Formula (s53) or formula (s54)

[Wherein A70 represents a methyl group, ethyl group, isopropyl group, 2,2,2-trifluoroethyl group, or phenyl group, and A71 is

A72 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 -. ] Compounds represented by (see WO 14/167084 and WO 16/055431),

［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-28.138] Formula (s55)

[In the formula, m11 represents an integer of 0 to 1, A73 represents a chlorine atom, a bromine atom, a methyl group, or a trifluoromethyl group, and 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, and A76 and A77 each independently represent a C1 to C6 alkyl group or a C3 to 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),

［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-28.139] Formula (s56)

[In the formula, A79, A80, A81 and A82 are each independently a hydrogen atom, a halogen atom, a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, a C1 to C6 alkoxy group, or a C3 to C8 represents a cycloalkoxy group. ] (see WO 12/027521),

［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-28.140] Formula (s57)

[In the formula, m12 represents an integer of 0 to 2, A83 represents a hydrogen atom or a fluorine atom, and A84 is

represents a substructure selected from the group consisting of ] (see WO 13/162715),

[c-28.141] acynonapyr,

［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、プロピオニル基、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-28.142] Formula (s59)

[A90 represents a halogen atom, a C1 to C6 alkyl group, or a C1 to C6 haloalkyl group, A91 represents a C1 to C6 haloalkyl group, A92 and A93 are each independently a hydrogen atom, Represents a C1 to C6 alkyl group, acetyl group, propionyl group, methanesulfonylethyl group, methoxycarbonyl group, or ethoxycarbonyl group, A94 and A95 are each independently a hydrogen atom, a C1 to C6 alkyl group, Or represents a C1 to C6 haloalkyl group. ] (see International Publication No. 12/164698).

The mixing ratio of the compound of the present invention and other agricultural chemicals that can be mixed and used as necessary as described above is not particularly limited as long as the effect is exerted; The weight ratio of other agricultural chemicals is 0.001 to 1000, preferably 0.01 to 100.

The present invention will be illustrated in more detail below with reference to synthesis examples, reference examples, and test examples, but the present invention is not limited thereto.

[Synthesis example 1]
Synthesis of 3-chloro-5-(5-chloro-1H-pyrazol-1-yl)-6-(2,6-difluorophenyl)-1-ethylpyridin-2(1H)-one (compound number: A- 001)

5-(4-Amino-5-chloro-1H-pyrazol-1-yl)-3-chloro-6-(2,6-difluorophenyl)-1-ethylpyridin-2(1H)-one 116 mg and 50% To 3 ml of ethanol solution containing 176 μl of hypophosphorous acid aqueous solution, 39 μl of t-butyl nitrite was added at 0°C, and the mixture was stirred at 40°C for 25 minutes. 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 brine and dried over sodium sulfate. After distilling off the solvent under reduced pressure, the resulting residue was purified by silica gel column chromatography. The title compound was obtained as 40 mg of a pale yellow solid.

[Synthesis example 2]
3-chloro-5-(5-chloro-1H-pyrazol-1-yl)-1-(2,2-difluoroethyl)-6-(2,6-difluorophenyl)pyridin-2(1H)-one Synthesis (compound number: A-022)

5-(4-amino-5-chloro-1H-pyrazol-1-yl)-3-chloro-1-(2,2-difluoroethyl)-6-(2,6-difluorophenyl)pyridine-2(1H 3 ml of an ethanol solution containing 124 mg of )-one, 38 μl of t-butyl nitrite, and 1.5 ml of a 50% aqueous hypophosphorous acid solution was stirred at 40° C. for 10 minutes. 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 brine and dried over sodium sulfate. After distilling off the solvent under reduced pressure, the resulting residue was purified by silica gel column chromatography. The title compound was obtained as 56 mg of a white solid.

[Synthesis example 3]
Synthesis of 1-(5-chloro-2-(2,6-difluorophenyl)-1-ethyl-6-oxo-1,6-dihydropyridin-3-yl)-1H-pyrazole-5-carbaldehyde (compound no. :A-054)

4-Amino-1-(5-chloro-2-(2,6-difluorophenyl)-1-ethyl-6-oxo-1,6-dihydropyridin-3-yl)-1H-pyrazole-5-carbaldehyde 800mg , 10 ml of an ethanol solution containing 275 μl of t-butyl nitrite and 10 ml of a 50% aqueous hypophosphorous acid solution was stirred at 40° C. for 10 minutes. 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 brine and dried over magnesium sulfate. After distilling off the solvent under reduced pressure, the resulting residue was purified by silica gel column chromatography. The title compound was obtained as 253 mg of yellow amorphous.

[Synthesis example 4]
Synthesis of 3-chloro-6-(2,6-difluorophenyl)-1-ethyl-5-(5-ethynyl-1H-pyrazol-1-yl)pyridin-2(1H)-one (compound number: A- 068)

1-(5-chloro-2-(2,6-difluorophenyl)-1-ethyl-6-oxo-1,6-dihydropyridin-3-yl)-1H-pyrazole-5-carbaldehyde 60 mg, (1- 3 ml of a methanol solution containing 37 μl of dimethyl diazo-2-oxopropyl)phosphonate and 34 mg of potassium carbonate was stirred at room temperature for 4 hours. Water and ethyl acetate were added to the reaction mixture to separate the layers. The obtained organic layer was washed with saturated brine and dried over magnesium sulfate. After distilling off the solvent under reduced pressure, the resulting residue was purified by silica gel column chromatography. The title compound was obtained as 58 mg of white amorphous.

[Synthesis example 5]
1-(5-chloro-2-(2,6-difluorophenyl)-1-ethyl-6-oxo-1,6-dihydropyridin-3-yl)-1H-pyrazole-5-carbaldehyde O-methyloxime Synthesis (compound number: A-069)

1-(5-chloro-2-(2,6-difluorophenyl)-1-ethyl-6-oxo-1,6-dihydropyridin-3-yl)-1H-pyrazole-5-carbaldehyde 60 mg, O-methyl 3 ml of an ethanol solution containing 28 mg of hydroxylamine hydrochloride and 27 μl of pyridine was stirred at 80° C. for 55 minutes. 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 brine and dried over magnesium sulfate. After distilling off the solvent under reduced pressure, the resulting residue was purified by silica gel column chromatography. The title compound was obtained as 64 mg of pale yellow amorphous.

[Synthesis example 6]
Synthesis of 3-chloro-6-(2,6-difluorophenyl)-1-ethyl-5-(5-(1-hydroxyethyl)-1H-pyrazol-1-yl)pyridin-2(1H)-one ( Compound number: A-079)

THF solution containing 159 mg of 1-(5-chloro-2-(2,6-difluorophenyl)-1-ethyl-6-oxo-1,6-dihydropyridin-3-yl)-1H-pyrazole-5-carbaldehyde 217 μl of a 3 mol/L THF solution of methylmagnesium chloride was added dropwise to 5 ml at −78° C., and the mixture was stirred for 50 minutes. A saturated aqueous ammonium chloride solution and ethyl acetate were added to the reaction mixture to separate the layers. The obtained organic layer was washed with saturated brine and dried over sodium sulfate. After distilling off the solvent under reduced pressure, the resulting residue was purified by silica gel column chromatography. The title compound was obtained as 132 mg of a white solid.

[Synthesis example 7]
Synthesis of 3-chloro-6-(2,6-difluorophenyl)-1-ethyl-5-(5-vinyl-1H-pyrazol-1-yl)pyridin-2(1H)-one (compound number: A- 080)

3-chloro-6-(2,6-difluorophenyl)-1-ethyl-5-(5-(1-hydroxyethyl)-1H-pyrazol-1-yl)pyridin-2(1H)-one 100 mg and 85 5 ml of dioxane solution containing 45 μl of % phosphoric acid aqueous solution was stirred under reflux for 85 minutes. Further, 45 μl of 85% phosphoric acid aqueous solution was added, and the mixture was stirred under reflux for 2 hours. Furthermore, 75 mg of p-toluenesulfonic acid monohydrate was added, and the mixture was stirred under reflux for 8 hours. After cooling to room temperature, a saturated aqueous sodium hydrogen carbonate solution and ethyl acetate were added to the reaction mixture to separate the layers. The obtained organic layer was washed with saturated brine and dried over magnesium sulfate. After distilling off the solvent under reduced pressure, the resulting residue was purified by silica gel column chromatography. The title compound was obtained as 80 mg of a white solid.

[Synthesis example 8]
Synthesis of 3-chloro-6-(2,6-difluorophenyl)-1-ethyl-5-(5-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-2(1H)-one (compound Number: A-003)

220 mg of tert-butyl 1-(5-chloro-2-(2,6-difluorophenyl)-1-ethyl-6-oxo-1,6-dihydropyridin-3-yl)hydrazine-1-carboxylate and 4-ethoxy 196 μl of a 4N hydrogen chloride dioxane solution was added to 3 ml of an ethanol solution containing 138 μl of -1,1,1-trifluoro-3-buten-2-one, and the mixture was stirred at 90° C. for 30 minutes. After cooling to room temperature, a saturated aqueous sodium hydrogen carbonate solution and ethyl acetate were added to the reaction mixture to separate the layers. The obtained organic layer was washed with saturated brine and then dried over sodium sulfate. After distilling off the solvent under reduced pressure, the resulting residue was purified by silica gel column chromatography. The title compound was obtained as 172 mg of a white solid.

[Reference example 1]
Synthesis of 1-(2,6-difluorophenyl)-2-(4-nitro-1H-pyrazol-1-yl)ethane-1-one

To 20 ml of a DMF solution containing 1.62 g of 60% sodium hydride (dispersed in liquid paraffin), 3.81 g of 4-nitropyrazole was added under ice cooling, and the mixture was stirred for 10 minutes. Next, 20 ml of a DMF solution containing 10.3 g of 2-bromo-1-(2,6-difluorophenyl)ethane-1-one was added dropwise under ice cooling, and the mixture was stirred for 15 minutes. A saturated aqueous ammonium chloride solution and ethyl acetate were added to the reaction mixture to separate the layers. The obtained organic layer was washed with saturated brine and then dried over sodium sulfate. After distilling off the solvent under reduced pressure, the precipitate was washed with diisopropyl ether. The orange solid obtained was the title compound and weighed 6.27 g.

¹ H-NMR (CDCl ₃ ) δ: 8.28 (1H, s), 8.12 (1H, s), 7.57-7.55 (1H, m), 7.07-7.05 (2H , m), 5.46 (2H, s).

[Reference example 2]
Synthesis of ethyl 5-(2,6-difluorophenyl)-4-(4-nitro-1H-pyrazol-1-yl)-5-oxopentanoate

To 60 ml of THF solution containing 6.27 g of 1-(2,6-difluorophenyl)-2-(4-nitro-1H-pyrazol-1-yl)ethan-1-one, 527 mg of potassium t-butoxide and ethyl acrylate were added. 2.68 ml was added and stirred at room temperature for 35 minutes. Further, 527 mg of potassium t-butoxide was added, and the mixture was stirred at room temperature for 25 minutes. A saturated ammonium chloride solution and ethyl acetate were added to this to separate the layers, and the resulting organic layer was washed with saturated brine and dried over sodium sulfate. After evaporation of the solvent under reduced pressure, 7.57 g of a red oil containing the title compound were obtained. It was used in the next reaction without further purification.

^1H -NMR ( _CDCl3 ) δ: 8.31 (1H, s), 8.04 (1H, s), 7.45-7.43 (1H, m), 6.99-6.93 (2H , m), 5.73 (1H, dd, J = 10.4, 4.5 Hz), 4.14 (2H, q, J = 7.2 Hz), 2.66-1.63 (1H, m), 2.45-2.36 (2H, m), 2.19-2.16 (1H, m), 1.25 (3H, t, J = 7.2 Hz).

[Reference example 3]
Synthesis of 6-(2,6-difluorophenyl)-5-(4-nitro-1H-pyrazol-1-yl)-3,4-dihydropyridin-2(1H)-one

7.57 g of ethyl 5-(2,6-difluorophenyl)-4-(4-nitro-1H-pyrazol-1-yl)-5-oxopentanoate obtained in Reference Example 2 and 31.8 g of ammonium acetate were added. 37.5 ml of the acetic acid solution containing the above was stirred at 120°C for 1 hour. After cooling to room temperature, ethyl acetate and water were added to the reaction mixture, and potassium carbonate was further added until foaming subsided, followed by liquid separation. The obtained organic layer was washed with saturated brine and dried over sodium sulfate. After distilling off the solvent under reduced pressure, the precipitate was washed with diisopropyl ether. The brown solid obtained was the title compound and weighed 2.98 g.

^1H -NMR ( _CDCl3 ) δ: 8.05 (1H, s), 7.84 (1H, s), 7.44-7.38 (1H, m), 6.97-6.95 (2H , m), 6.71 (1H, br s), 3.11-3.09 (2H, m), 2.91-2.89 (2H, m).

[Reference example 4]
Synthesis of 6-(2,6-difluorophenyl)-1-ethyl-5-(4-nitro-1H-pyrazol-1-yl)-3,4-dihydropyridin-2(1H)-one

Add iodine to 30 ml of a DMF solution containing 2.98 g of 6-(2,6-difluorophenyl)-5-(4-nitro-1H-pyrazol-1-yl)-3,4-dihydropyridin-2(1H)-one. 1.49 ml of ethyl chloride and 6.06 g of cesium carbonate were added, and the mixture was stirred at 50°C for 1 hour. After cooling to room temperature, a saturated aqueous ammonium chloride solution and ethyl acetate were added to the reaction mixture to separate the layers. The obtained organic layer was washed successively with an aqueous sodium thiosulfate solution and saturated brine, and dried over sodium sulfate. After distilling off the solvent under reduced pressure, the resulting residue was purified by silica gel column chromatography. The title compound was obtained as 2.64 g of a yellow solid.

^1H -NMR ( _CDCl3 ) δ: 7.99 (1H, s), 7.87 (1H, s), 7.42-7.40 (1H, m), 6.98-6.93 (2H , m), 3.43 (2H, q, J = 7.0 Hz), 2.96-2.88 (4H, m), 0.98 (3H, t, J = 7.0 Hz).

[Reference example 5]
Synthesis of 6-(2,6-difluorophenyl)-1-ethyl-5-(4-nitro-1H-pyrazol-1-yl)pyridin-2(1H)-one (intermediate number: B-007)

Tetrachloride containing 2.64 g of 6-(2,6-difluorophenyl)-1-ethyl-5-(4-nitro-1H-pyrazol-1-yl)-3,4-dihydropyridin-2(1H)-one 1.42 g of N-bromosuccinimide and 62 mg of azobisisobutyronitrile were added to 52 ml of the carbon solution, and the mixture was stirred at 90° C. for 85 minutes. After cooling to room temperature, dichloromethane and water were added to separate the layers. The obtained organic layer was washed with sodium thiosulfate and dried over sodium sulfate. After distilling off the solvent under reduced pressure, the resulting residue was purified by silica gel column chromatography. The title compound was obtained as 2.37 g of a pale yellow solid.

[Reference example 6]
Synthesis of 3-chloro-6-(2,6-difluorophenyl)-1-ethyl-5-(4-nitro-1H-pyrazol-1-yl)pyridin-2(1H)-one (intermediate number; B -22)

DMF containing 1.12 g of 6-(2,6-difluorophenyl)-1-ethyl-5-(4-nitro-1H-pyrazol-1-yl)pyridin-2(1H)-one and 648 mg of N-chlorosuccinimide. 11 ml of the solution was stirred at 70°C for 110 minutes. 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 successively with sodium thiosulfate and saturated brine, and dried over sodium sulfate. After distilling off the solvent under reduced pressure, the resulting residue was purified by silica gel column chromatography. The title compound was obtained as 1.23 g of a white solid.

[Reference example 7]
Synthesis of 3-chloro-5-(5-chloro-4-nitro-1H-pyrazol-1-yl)-6-(2,6-difluorophenyl)-1-ethylpyridin-2(1H)-one (intermediate Body number: B-33)

6 ml of THF solution containing 615 mg of 3-chloro-6-(2,6-difluorophenyl)-1-ethyl-5-(4-nitro-1H-pyrazol-1-yl)pyridin-2(1H)-one, 1.62 ml of a 1.3 mol/L THF solution of lithium hexamethyldisilazane was added dropwise at -78°C, and the mixture was stirred for 10 minutes. Next, 6 ml of a THF solution containing 574 mg of hexachloroethane was added dropwise at -78°C and stirred for 10 minutes. A saturated aqueous ammonium chloride solution and ethyl acetate were added to the reaction mixture to separate the layers. The obtained organic layer was washed with saturated brine and dried over sodium sulfate. After distilling off the solvent under reduced pressure, the resulting residue was purified by silica gel column chromatography. The title compound was obtained as 606 mg of yellow amorphous.

[Reference example 8]
Synthesis of 5-(4-amino-5-chloro-1H-pyrazol-1-yl)-3-chloro-6-(2,6-difluorophenyl)-1-ethylpyridin-2(1H)-one (intermediate Body number: B-001)

3-chloro-5-(5-chloro-4-nitro-1H-pyrazol-1-yl)-6-(2,6-difluorophenyl)-1-ethylpyridin-2(1H)-one 606 mg and iron 408 mg A mixed solution of 6 ml of ethanol and 3 ml of 6N hydrochloric acid was stirred at 80° C. for 30 minutes. Furthermore, 204 mg of iron was added, and the mixture was stirred at 80° C. for 10 minutes. After cooling to room temperature, the reaction mixture was filtered through Celite, and a saturated aqueous sodium hydrogen carbonate solution and ethyl acetate were added to separate the layers. The obtained organic layer was washed with saturated brine and dried over sodium sulfate. After distilling off the solvent under reduced pressure, the resulting residue was purified by silica gel column chromatography. The title compound was obtained as 395 mg of a brown solid.

Reference Example 8 and Synthesis Example 1 show that a compound having an amino group derived by reduction of a nitro group can be a useful intermediate for obtaining the compound of the present invention.

で表される製造中間体と、表７には表６に該当する製造中間体の^１Ｈ－ＮＭＲデータを示す。Table 6 shows the following structural formula

Table 7 shows ¹ H-NMR data of the production intermediates corresponding to Table 6.

[Reference example 9]
1-(2,2-difluoroethyl)-6-(2,6-difluorophenyl)-5-(4-nitro-1H-pyrazol-1-yl)-3,4-dihydropyridin-2(1H)-one synthesis of

6-(2,6-difluorophenyl)-5-(4-nitro-1H-pyrazol-1-yl)-3,4-dihydropyridin-2(1H)-one 2.39 g, p-toluenesulfonic acid 2, 24 ml of a DMF solution containing 3.53 g of 2-difluoroethyl and 4.86 g of cesium carbonate was stirred at 60° C. for 1 hour. After cooling to room temperature, a saturated aqueous ammonium chloride solution and ethyl acetate were added to the reaction mixture to separate the layers. The obtained organic layer was washed with saturated brine and dried over sodium sulfate. After distilling off the solvent under reduced pressure, the resulting residue was purified by silica gel column chromatography. The title compound was obtained as 2.20 g of a yellow solid.

^1H -NMR ( _CDCl3 ) δ: 8.00 (1H, s), 7.88 (1H, s), 7.48-7.42 (1H, m), 6.98-6.96 (2H , m), 5.90 (1H, tt, J = 56.4, 4.4 Hz), 3.70 (2H, td, J = 13.4, 4.4 Hz), 3.02-2. 98 (2H, m), 2.97-2.94 (2H, m).

[Reference example 10]
Synthesis of 1-(2,2-difluoroethyl)-6-(2,6-difluorophenyl)-5-(4-nitro-1H-pyrazol-1-yl)pyridin-2(1H)-one (intermediate Number; B-34)

1-(2,2-difluoroethyl)-6-(2,6-difluorophenyl)-5-(4-nitro-1H-pyrazol-1-yl)-3,4-dihydropyridin-2(1H)-one 1.07 g of N-bromosuccinimide and 47 mg of azobisisobutyronitrile were added to 45 ml of a carbon tetrachloride solution containing 2.20 g, and the mixture was stirred at 90° C. for 85 minutes. After cooling to room temperature, dichloromethane and water were added to separate the layers. The obtained organic layer was washed with sodium thiosulfate and dried over sodium sulfate. After distilling off the solvent under reduced pressure, the resulting residue was purified by silica gel column chromatography. The title compound was obtained as 2.03 g of yellow amorphous.

[Reference example 11]
3-chloro-1-(2,2-difluoroethyl)-6-(2,6-difluorophenyl)-5-(4-nitro-1H-pyrazol-1-yl)pyridin-2(1H)-one Synthesis (intermediate number; B-35)

1-(2,2-difluoroethyl)-6-(2,6-difluorophenyl)-5-(4-nitro-1H-pyrazol-1-yl)pyridin-2(1H)-one and N-chloro 10 ml of a DMF solution containing 524 mg of succinimide was stirred at 70° C. for 2 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 successively with sodium thiosulfate and saturated brine, and dried over sodium sulfate. After distilling off the solvent under reduced pressure, the resulting residue was purified by silica gel column chromatography. The title compound was obtained as 880 mg of a white solid.

[Reference example 12]
3-chloro-5-(5-chloro-4-nitro-1H-pyrazol-1-yl)-1-(2,2-difluoroethyl)-6-(2,6-difluorophenyl)pyridine-2(1H )-one synthesis (intermediate number; B-36)

3-chloro-1-(2,2-difluoroethyl)-6-(2,6-difluorophenyl)-5-(4-nitro-1H-pyrazol-1-yl)pyridin-2(1H)-one 169 mg 406 μl of a 1.3 mol/L THF solution of lithium hexamethyldisilazane was added dropwise to 2 ml of a THF solution containing lithium hexamethyldisilazane at −78° C., and the mixture was stirred for 10 minutes. Next, 2 ml of a THF solution containing 125 mg of hexachloroethane was added dropwise at -78°C, and the mixture was stirred for 10 minutes. A saturated aqueous ammonium chloride solution and ethyl acetate were added to the reaction mixture to separate the layers. The obtained organic layer was washed with saturated brine and dried over sodium sulfate. After distilling off the solvent under reduced pressure, the resulting residue was purified by silica gel column chromatography. The title compound was obtained as 151 mg of a pale yellow solid.

[Reference example 13]
5-(4-amino-5-chloro-1H-pyrazol-1-yl)-3-chloro-1-(2,2-difluoroethyl)-6-(2,6-difluorophenyl)pyridine-2(1H )-one synthesis (intermediate number; B-037)

3-chloro-5-(5-chloro-4-nitro-1H-pyrazol-1-yl)-1-(2,2-difluoroethyl)-6-(2,6-difluorophenyl)pyridine-2(1H A mixed solution of 3 ml of ethanol and 1 ml of water containing 151 mg of )-one, 56 mg of iron, and 18 mg of ammonium chloride was stirred at 80° C. for 45 minutes. After cooling to room temperature, the reaction mixture was filtered through Celite, and a saturated aqueous sodium hydrogen carbonate solution and ethyl acetate were added to separate the layers. The obtained organic layer was washed with saturated brine and dried over sodium sulfate. After distilling off the solvent under reduced pressure, the resulting residue was purified by silica gel column chromatography. The title compound was obtained as 124 mg of an orange solid.

[Reference example 14]
1-(5-chloro-2-(2,6-difluorophenyl)-1-ethyl-6-oxo-1,6-dihydropyridin-3-yl)-4-nitro-1H-pyrazole-5-carbaldehyde Synthesis (intermediate number; B-38)

60 ml of THF solution containing 2.97 g of 3-chloro-6-(2,6-difluorophenyl)-1-ethyl-5-(4-nitro-1H-pyrazol-1-yl)pyridin-2(1H)-one 23.4 ml of a 1 mol/L THF solution of lithium hexamethyldisilazane was added dropwise at -78°C, and the mixture was stirred for 10 minutes. Next, 10 ml of a THF solution containing 5 ml of ethyl formate was added dropwise at -78°C, and the mixture was stirred for 80 minutes. A saturated aqueous ammonium chloride solution and ethyl acetate were added to the reaction mixture to separate the layers. The obtained organic layer was washed with saturated brine and dried over magnesium sulfate. After distilling off the solvent under reduced pressure, the resulting residue was purified by silica gel column chromatography. The title compound was obtained as 2.16 g of a yellow solid.

[Reference example 15]
4-amino-1-(5-chloro-2-(2,6-difluorophenyl)-1-ethyl-6-oxo-1,6-dihydropyridin-3-yl)-1H-pyrazole-5-carbaldehyde Synthesis (intermediate number; B-39)

1-(5-chloro-2-(2,6-difluorophenyl)-1-ethyl-6-oxo-1,6-dihydropyridin-3-yl)-4-nitro-1H-pyrazole-5-carbaldehyde 2 A mixed solution of 30 ml of ethanol and 15 ml of water containing 16 g of iron, 882 mg of iron, and 285 mg of ammonium chloride was stirred at 80° C. for 2 hours. After cooling to room temperature, the reaction mixture was filtered through Celite, and a saturated aqueous sodium hydrogen carbonate solution and ethyl acetate were added to separate the layers. The obtained organic layer was washed with saturated brine and dried over magnesium sulfate. After distilling off the solvent under reduced pressure, the precipitate was washed with diisopropyl ether. The brown solid obtained was the title compound and weighed 1.87 g.

ステップ１：１－（２，６－ジフルオロフェニル）－Ｎ－フェニルプロパン－１－イミンの合成
アニリン １１．７４ｇとトリエチルアミン １７．０１ｇを含むジクロロメタン溶液 １００ｍｌに、四塩化チタン２３．９１ｇを含むジクロロメタン溶液 ５０ｍｌを氷冷下で滴下した。該反応液に１－（２，６－ジフルオロフェニル）プロパン－１－オン １４．３０ｇを含むジクロロメタン溶液 ３０ｍｌを滴下した後に、氷冷から室温まで昇温して終夜撹拌した。得られた反応混合物に１規定塩酸を加えて分液し、硫酸ナトリウムで乾燥した。減圧下で溶媒留去した後に、表題の化合物を含む２１．１０ｇの濃緑色油状物質が得られた。これ以上精製することなく、次の反応に使用した。[Reference example 16]

Step 1: Synthesis of 1-(2,6-difluorophenyl)-N-phenylpropan-1-imine A dichloromethane solution containing 11.74 g of aniline and 17.01 g of triethylamine A dichloromethane solution containing 23.91 g of titanium tetrachloride in 100 ml 50 ml was added dropwise under ice cooling. After 30 ml of a dichloromethane solution containing 14.30 g of 1-(2,6-difluorophenyl)propan-1-one was added dropwise to the reaction solution, the temperature was raised from ice cooling to room temperature and stirred overnight. 1N hydrochloric acid was added to the resulting reaction mixture to separate the layers, and the mixture was dried over sodium sulfate. After evaporating the solvent under reduced pressure, 21.10 g of a dark green oil was obtained containing the title compound. It was used in the next reaction without further purification.

Step 2: Synthesis of 6-(2,6-difluorophenyl)-5-methyl-3,4-dihydropyridin-2(1H)-one 1-(2,6-difluorophenyl)-N obtained in Step 1 - 6.57 g of acrylamide monomer was added to 200 ml of a dioxane solution containing 21.10 g of phenylpropan-1-imine and 12.33 g of aluminum chloride, and the mixture was stirred at 90° C. for 3 hours. After distilling the solvent off of the reaction mixture to about half its volume under reduced pressure, 1N hydrochloric acid and ethyl acetate were added to separate the mixture. The obtained organic layer was washed with saturated brine and dried over sodium sulfate. After distilling off the solvent under reduced pressure, the resulting residue was purified by silica gel column chromatography. The resulting solid was washed with isopropyl ether to yield 11.65 g of the title compound as a white solid.

¹ H-NMR (CDCl ₃ ) δ: 7.36-7.34 (1H, m), 6.97-6.94 (2H, m), 6.52 (1H, br s), 2.61- 2.59 (2H, m), 2.48-2.47 (2H, m), 1.63 (3H, s).

[Reference example 17]
Synthesis of 6-(2,6-difluorophenyl)-1-ethyl-5-methyl-3,4-dihydropyridin-2(1H)-one

50 ml of a DMF solution containing 12.40 g of 6-(2,6-difluorophenyl)-5-methyl-3,4-dihydropyridin-2(1H)-one, 54.30 g of cesium carbonate and 25.99 g of ethyl iodide Stirred at ℃ for 3.5 hours. Next, 27.15 g of cesium carbonate and 13.01 g of ethyl iodide were added, followed by stirring at 50°C for 2 hours and further at 60°C for 1.5 hours. After cooling to room temperature, the reaction mixture was filtered to remove insoluble matter. After distilling off the solvent from the filtrate under reduced pressure, ethyl acetate and water were added to separate the layers. The obtained organic layer was washed successively with an aqueous sodium thiosulfate solution and saturated brine, and dried over sodium sulfate. After evaporating the solvent under reduced pressure, the resulting solid was washed with isopropyl ether. The title compound was obtained as 11.98 g of a white solid.

¹ H-NMR (CDCl ₃ ) δ: 7.38-7.35 (1H, m), 6.97-6.96 (2H, m), 3.33 (2H, q, J = 7.1 Hz ), 2.60-2.58 (2H, m), 2.38-2.36 (2H, m), 1.59 (3H, s), 0.91 (3H, t, J = 7.1 Hz).

[Reference example 18]
Synthesis of 6-(2,6-difluorophenyl)-1-ethyl-5-methylpyridin-2(1H)-one

11.98 g of 6-(2,6-difluorophenyl)-1-ethyl-5-methyl-3,4-dihydropyridin-2(1H)-one and 2,3-dichloro-5,6-dicyano-p-benzoquinone 170 ml of a toluene solution containing 21.65 g was stirred at 120° C. for 1.5 hours. After cooling to room temperature, the reaction mixture was filtered to remove insoluble matter. After distilling off the solvent from the filtrate under reduced pressure, the resulting residue was purified by silica gel column chromatography. The resulting solid was washed with isopropyl ether to obtain 9.34 g of the title compound as a pale yellow solid.

¹ H-NMR (CDCl ₃ ) δ: 7.50-7.49 (1H, m), 7.27 (2H, d, J = 9.5 Hz), 7.09-7.06 (2H, m ), 6.63 (1H, d, J = 9.5 Hz), 3.83 (2H, q, J = 7.1 Hz), 1.80 (3H, s), 1.10 (3H, t , J = 7.1 Hz).

[Reference example 19]
Synthesis of 3-chloro-6-(2,6-difluorophenyl)-1-ethyl-5-methylpyridin-2(1H)-one

110 ml of a DMF solution containing 11.36 g of 6-(2,6-difluorophenyl)-1-ethyl-5-methylpyridin-2(1H)-one and 6.69 g of N-chlorosuccinimide was stirred at 70°C for 50 minutes. . After cooling to room temperature, the reaction mixture was evaporated under reduced pressure. After adding ethyl acetate and water to separate the layers, the obtained organic layer was washed successively with an aqueous sodium thiosulfate solution and saturated brine, and dried over sodium sulfate. After evaporating the solvent under reduced pressure, the resulting solid was washed with isopropyl ether. The title compound was obtained as 11.41 g of a white solid.

^1H -NMR ( _CDCl3 ) δ: 7.53-7.49 (1H, m), 7.50 (1H, s), 7.09-7.07 (2H, m), 3.88 (2H , q, J = 7.1 Hz), 1.81 (3H, s), 1.12 (3H, t, J = 7.1 Hz).

[Reference example 20]
Synthesis of 3-chloro-5-(dibromomethyl)-6-(2,6-difluorophenyl)-1-ethylpyridin-2(1H)-one

To 230 ml of a chlorobenzene solution containing 12.65 g of 3-chloro-6-(2,6-difluorophenyl)-1-ethyl-5-methylpyridin-2(1H)-one, 16.67 g of N-bromosuccinimide and azobis 366 mg of isobutyronitrile was added and stirred at 110°C for 50 minutes. After cooling to room temperature, water and dichloromethane were added to the reaction mixture to separate the layers. The obtained organic layer was washed with an aqueous sodium thiosulfate solution and dried over sodium sulfate. After evaporating the solvent under reduced pressure, the resulting solid was washed with isopropyl ether. The title compound was obtained as 16.88 g of a light brown solid.

^1H -NMR ( _CDCl3 ) δ: 8.13 (1H, s), 7.65-7.63 (1H, m), 7.18 (2H, dd, J = 8.5, 6.8 Hz ), 5.96 (1H, s), 3.82 (2H, q, J = 7.1 Hz), 1.13 (3H, t, J = 7.1 Hz).

[Reference example 21]
Synthesis of 5-chloro-2-(2,6-difluorophenyl)-1-ethyl-6-oxo-1,6-dihydropyridine-3-carbaldehyde

190 ml of an aqueous solution containing 21.87 g of silver nitrate in 380 ml of acetonitrile containing 18.95 g of 3-chloro-5-(dibromomethyl)-6-(2,6-difluorophenyl)-1-ethylpyridin-2(1H)-one was added and stirred at room temperature for 15 minutes. The resulting reaction mixture was filtered to remove insoluble matter. After distilling off the solvent of the filtrate under reduced pressure, water and ethyl acetate were added to separate the layers. The obtained organic layer was washed with 1N hydrochloric acid and saturated brine, and dried over sodium sulfate. After evaporating the solvent under reduced pressure, the resulting solid was washed with isopropyl ether. The title compound was obtained as 11.37 g of a pale yellow solid.

¹ H-NMR (CDCl ₃ ) δ: 9.19 (1H, t, J = 1.0 Hz), 8.13 (1H, s), 7.67-7.63 (1H, m), 7. 18-7.16 (2H, m), 3.94 (2H, q, J = 7.1 Hz), 1.19 (3H, t, J = 7.1 Hz).

[Reference example 22]
Synthesis of 5-chloro-2-(2,6-difluorophenyl)-1-ethyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid

5-chloro-2-(2,6-difluorophenyl)-1-ethyl-6-oxo-1,6-dihydropyridine-3-carbaldehyde 1.5 g, 2-methyl-2-butene 2.36 ml and phosphoric acid To a mixed solution of 6.75 ml of water, 20.25 ml of THF, and 20.25 ml of tert-butanol containing 786 mg of sodium dihydrogen dihydrate, 1.71 g of 80% by weight sodium chlorite was added and the mixture was heated to 2.5 ml at room temperature. Stir for hours. After water and ethyl acetate were added to the reaction mixture to separate the layers, the resulting organic layer was washed successively with an aqueous sodium thiosulfate solution and saturated brine, and dried over sodium sulfate. After evaporating the solvent under reduced pressure, the resulting solid was washed with isopropyl ether. The title compound was obtained as 1.42 g of a white solid.

¹ H-NMR (CDCl ₃ ) δ: 8.21 (1H, s), 7.54-7.50 (1H, m), 7.05-7.04 (2H, m), 3.93 (2H , q, J = 7.2 Hz), 1.16 (3H, t, J = 7.2 Hz).

[Reference example 23]
Synthesis of tert-butyl (5-chloro-2-(2,6-difluorophenyl)-1-ethyl-6-oxo-1,6-dihydropyridin-3-yl)carbamate

2. To 20 ml of tert-butanol containing 1.42 g of 5-chloro-2-(2,6-difluorophenyl)-1-ethyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid, diphenylphosphoric azide was added. 93 ml and 1.89 ml of triethylamine were added, and the mixture was stirred at room temperature for 1 hour and further at 80°C for 2 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 brine and then dried over sodium sulfate. After distilling off the solvent under reduced pressure, the obtained solid was washed with a mixed solvent of ethyl acetate and isopropyl ether. The title compound was obtained as 1.09 g of a white solid.

^1H -NMR ( _CDCl3 ) δ: 7.86 (1H, br s), 7.56-7.54 (1H, m), 7.11-7.09 (2H, m), 5.59 ( 1H, br s), 3.90 (2H, q, J = 7.1 Hz), 1.35 (9H, s), 1.12 (3H, t, J = 7.1 Hz).

[Reference example 24]
Synthesis of tert-butyl 1-(5-chloro-2-(2,6-difluorophenyl)-1-ethyl-6-oxo-1,6-dihydropyridin-3-yl)hydrazine-1-carboxylate

((5-chloro-2-(2,6-difluorophenyl)-1-ethyl-6-oxo-1,6-dihydropyridine- 20 ml of a DMF solution containing 2.02 g of tert-butyl 3-yl)carbamate was added dropwise under ice cooling and stirred for 5 minutes.Next, after adding 1.59 g of O-(diphenylphosphinyl)hydroxylamine, The temperature was raised from ice cooling to room temperature and stirred for 20 minutes.The reaction mixture was cooled again with ice, and saturated ammonium chloride solution and ethyl acetate were added to separate the layers.The obtained organic layer was washed with saturated brine. , and dried over sodium sulfate. After evaporating the solvent under reduced pressure, the resulting residue was purified by silica gel column chromatography. 1.76 g of the title compound was obtained as a white solid.

¹ H-NMR (CDCl ₃ ) δ: 7.54-7.48 (2H, m), 7.07-7.05 (2H, m), 4.13 (2H, br s), 3.93- 3.90 (2H, br m), 1.33 (9H, s), 1.14 (3H, t, J = 7.1 Hz).

Table 8 shows compounds synthesized according to the examples described above, but the present invention is not limited thereto.

The structural formula in Table 8 is as follows.

Next, Table 9 shows ¹ H-NMR data for the compounds listed in Table 8.

Next, it will be specifically shown that the compounds of the present invention are effective against plant diseases, but the invention is not limited to these examples.

Regarding the degree of disease onset in the test examples shown below, the degree of disease onset was evaluated in increments of 0.05, with the degree of disease onset of plants without disease being 0, and the degree of disease onset of plants in the no-chemical treatment area being 3. In addition, the control value was calculated based on the degree of disease onset according to the formula below.

<Prevention value>
Control value = 100 {1-(n/3)}
n = degree of disease onset in each chemical treatment area

[Test Example A] Rice blast After sowing seeds of a test plant (rice variety: Kofu), the plants were cultivated until the second leaves developed. In the test, the compound of the present invention was dissolved in a mixed solution of dimethyl sulfoxide and methanol (volume ratio: 9/1) and diluted with well water to a concentration of 250 ppm to obtain a drug solution. The obtained chemical solution was sprayed on test plants (2.5 ml/pot). After the chemical solution had dried, the plants were inoculated by spraying with a conidial suspension of 1 to 2×10 ⁵ cells/ml of the rice blast fungus (Magnaporthe grisea). After inoculation, the plants were left in a humid room at a room temperature of 20 to 23°C for about 24 hours to promote disease development. The degree of disease onset was investigated 6 to 10 days after inoculation, and the effectiveness of the drug solution was evaluated.

As a result, the compounds shown below showed a control value greater than 50%.
Compound number: A-001, A-002, A-003, A-004, A-005, A-006, A-008, A-009, A-010, A-011, A-012, A-013 , A-014, A-015, A-018, A-020, A-022, A-023, A-024, A-025, A-026, A-027, A-028, A-031, A -032, A-033, A-034, A-037, A-038, A-039, A-040, A-041, A-042, A-043, A-044, A-045, A-046 , A-047, A-048, A-049, A-050, A-052, A-053, A-055, A-056, A-057, A-058, A-059, A-060, A -061, A-062, A-063, A-064, A-065, A-067, A-068, A-069, A-070, A-071, A-072, A-073, A-074 , A-075, A-076, A-077, A-078, A-079, A-080, A-081, A-082, A-083, A-084, A-085, A-086, A -087, A-088, A-089, A-090, A-091, A-092, A-093, A-094, A-095, A-096, A-097, A-098, A-099 , A-102, A-103, A-112

[Test Example B] Tomato Botrytis Botrytis After sowing seeds of test plants (tomato variety: Large Fukuju), the plants were cultivated until 3 to 5 true leaves developed. In the test, the compound of the present invention was dissolved in a mixed solution of dimethyl sulfoxide and methanol (volume ratio: 9/1) and diluted with well water to a concentration of 250 ppm to obtain a drug solution. The obtained chemical solution was sprayed on test plants (2.5 ml/pot). After the chemical solution had dried, the plants were spray inoculated with a conidial suspension of Botrytis cinerea at 4 to 8 x 10 ⁵ cells/ml. After inoculation, the plants were left in a humid room at a room temperature of 20 to 23°C for about 48 hours to promote disease development. The degree of disease onset was investigated 2 to 3 days after inoculation, and the effectiveness of the drug solution was evaluated.

As a result, the compounds shown below showed a control value greater than 50%.
Compound number: A-001, A-002, A-003, A-004, A-005, A-006, A-008, A-009, A-010, A-012, A-013, A-014 , A-015, A-020, A-021, A-022, A-023, A-024, A-025, A-026, A-027, A-028, A-031, A-032, A -033, A-034, A-037, A-038, A-039, A-040, A-042, A-043, A-044, A-045, A-046, A-047, A-048 , A-049, A-050, A-052, A-053, A-054, A-055, A-056, A-057, A-058, A-059, A-061, A-063, A -064, A-065, A-067, A-068, A-070, A-072, A-073, A-074, A-075, A-076, A-077, A-078, A-080 , A-081, A-082, A-083, A-084, A-085, A-086, A-087, A-088, A-089, A-090, A-094, A-095, A -096, A-097, A-098, A-099, A-103, A-104, A-105, A-106, A-108, A-111, A-112

[Test Example C] Cabbage black soot disease Seeds of test plants (cabbage variety: Shikiharu) were sown and then cultivated until cotyledons developed. In the test, the compound of the present invention was dissolved in a mixed solution of dimethyl sulfoxide and methanol (volume ratio: 9/1) and diluted with well water to a concentration of 250 ppm to obtain a drug solution. The obtained chemical solution was sprayed on test plants (2.5 ml/pot). After the chemical solution had dried, the plants were inoculated by spraying with a conidial suspension of Alternaia brassicicola at a concentration of 4 to 8×10 ⁵ cells/ml. After inoculation, the plants were left in a humid room at a room temperature of 20 to 23°C for about 48 hours to promote disease development. The degree of disease onset was investigated 2 to 3 days after inoculation, and the effectiveness of the drug solution was evaluated.

As a result, the compounds shown below showed a control value greater than 50%.
Compound number: A-001, A-002, A-003, A-004, A-005, A-006, A-008, A-009, A-010, A-011, A-012, A-013 , A-014, A-015, A-018, A-019, A-020, A-021, A-022, A-023, A-024, A-025, A-026, A-027, A -028, A-031, A-032, A-033, A-034, A-037, A-038, A-039, A-040, A-041, A-042, A-043, A-044 , A-045, A-046, A-047, A-048, A-049, A-050, A-051, A-052, A-053, A-054, A-055, A-056, A -057, A-058, A-059, A-060, A-061, A-062, A-063, A-064, A-065, A-067, A-068, A-069, A-070 , A-071, A-072, A-073, A-074, A-075, A-076, A-077, A-078, A-080, A-081, A-082, A-083, A -084, A-085, A-086, A-087, A-088, A-090, A-092, A-093, A-094, A-095, A-096, A-097, A-098 , A-099, A-100, A-101, A-102, A-103, A-104, A-105, A-106, A-107, A-108, A-109, A-111, A -112, A-113

[Test Example D] Barley Powdery Mildew Seeds of test plants (barley variety: Akashinriki) were sown and then cultivated until the first leaves developed. In the test, the compound of the present invention was dissolved in a mixed solution of dimethyl sulfoxide and methanol (volume ratio: 9/1) and diluted with well water to a concentration of 250 ppm to obtain a drug solution. The obtained chemical solution was sprayed on test plants (2.5 ml/pot). After the chemical solution had dried, conidia of barley powdery mildew (Blumeria graminis f.sp.hordei) were knocked off and inoculated onto the plants. The degree of disease onset was investigated 6 to 10 days after inoculation to evaluate its effectiveness.

As a result, the compounds shown below showed a control value greater than 50%.
Compound number: A-001, A-002, A-003, A-005, A-006, A-008, A-009, A-011, A-012, A-013, A-014, A-018 , A-019, A-020, A-021, A-022, A-023, A-024, A-025, A-026, A-027, A-031, A-032, A-033, A -034, A-037, A-038, A-039, A-040, A-041, A-042, A-043, A-044, A-045, A-046, A-048, A-049 , A-050, A-052, A-053, A-055, A-056, A-057, A-061, A-062, A-068, A-069, A-070, A-072, A -073, A-074, A-075, A-076, A-077, A-078, A-080, A-081, A-082, A-085, A-086, A-087, A-088 , A-090, A-092, A-093, A-094, A-095, A-096, A-097, A-098, A-099, A-101, A-102, A-103, A -104, A-105, A-106, A-107, A-108, A-109, A-110, A-111, A-112, A-113

[Test Example E] Wheat rust After sowing seeds of test plants (wheat variety: Norin No. 61), the plants were cultivated until the first leaves developed. In the test, the compound of the present invention was dissolved in a mixed solution of dimethyl sulfoxide and methanol (volume ratio: 9/1) and diluted with well water to a concentration of 250 ppm to obtain a drug solution. The obtained chemical solution was sprayed on test plants (2.5 ml/pot). After the chemical solution had dried, the plants were inoculated by spraying with a suspension of 1 to 2 x 10 ⁵ wheat spores/ml of Puccinia recondita. After inoculation, the plants were left in a humid room at a room temperature of 20 to 23°C for about 24 hours to promote disease development. The degree of disease onset was investigated 7 to 10 days after inoculation, and the effectiveness of the drug solution was evaluated.

As a result, the compounds shown below showed a control value greater than 50%.
Compound number: A-001, A-002, A-003, A-004, A-005, A-006, A-007, A-008, A-009, A-012, A-013, A-014 , A-015, A-018, A-019, A-020, A-021, A-022, A-023, A-024, A-025, A-026, A-027, A-028, A -031, A-032, A-033, A-034, A-037, A-038, A-039, A-040, A-041, A-042, A-043, A-044, A-045 , A-046, A-047, A-048, A-049, A-050, A-053, A-055, A-056, A-057, A-061, A-062, A-063, A -064, A-065, A-067, A-068, A-069, A-070, A-072, A-073, A-074, A-075, A-076, A-077, A-078 , A-080, A-081, A-082, A-083, A-084, A-085, A-086, A-087, A-088, A-089, A-090, A-094, A -095, A-096, A-099, A-102, A-103, A-104, A-105, A-109, A-112

[Test Example F] Tomato Phytophthora Seeds of test plants (tomato cultivar: Large Fukuju) were sown and then cultivated until 3 to 5 true leaves developed. In the test, the compound of the present invention was dissolved in a mixed solution of dimethyl sulfoxide and methanol (volume ratio: 9/1) and diluted with well water to a concentration of 250 ppm to obtain a drug solution. The obtained chemical solution was sprayed on test plants (2.5 ml/pot). After the chemical solution had dried, the plants were inoculated by spraying with a zoospore suspension of Phytophthora infestans at a concentration of 4 to 8×10 ³ cells/ml. After inoculation, the plants were left in a humid room at a room temperature of 20°C for about 24 hours to encourage disease onset. The degree of disease onset was investigated 5 to 10 days after inoculation, and the effectiveness of the drug solution was evaluated.

As a result, the compounds shown below showed a control value greater than 50%.
Compound number: A-052, A-068, A-096, A-098, A-099, A-101, A-102, A-108

[Test Example G] Grape Downy Mildew Seeds of test plants (grape variety: Neomuscat) were sown and then cultivated until 3 to 4 true leaves developed. In the test, the compound of the present invention was dissolved in a mixed solution of dimethyl sulfoxide and methanol (volume ratio: 9/1) and diluted with well water to a concentration of 250 ppm to obtain a drug solution. The obtained chemical solution was sprayed on test plants (2.5 ml/pot). After the chemical solution had dried, the plants were inoculated by spraying with a suspension of zoosporangia of 1 to 2×10 ⁴ cells/ml of the grape downy mildew fungus (Plasmopara viticola). After inoculation, the plants were left in a humid room at a room temperature of 20°C for about 24 hours to encourage disease onset. The degree of disease onset was investigated 7 to 10 days after inoculation, and the effectiveness of the drug solution was evaluated.

As a result, the compounds shown below showed a control value greater than 50%.
Compound number: A-006, A-007, A-018, A-019, A-020, A-021, A-024, A-025, A-027, A-028, A-032, A-033 , A-037, A-039, A-041, A-042, A-043, A-044, A-045, A-046, A-050, A-068, A-071, A-075, A -081, A-082, A-088, A-094, A-095, A-096, A-097, A-104, A-105, A-108, A-109, A-112

[Test Example H] Cucumber anthracnose Seeds of test plants (cucumber variety: Sagami Hanjiro) were sown and then cultivated until one true leaf developed. In the test, the compound of the present invention was dissolved in a mixed solution of dimethyl sulfoxide and methanol (volume ratio: 9/1) and diluted with well water to a concentration of 250 ppm to obtain a drug solution. The obtained chemical solution was sprayed on test plants (2.5 ml/pot). After the chemical solution had dried, the plants were spray-inoculated with a conidial suspension of 2 to 4 x 10 ⁵ cells/ml of Colletotrichum orbiculare. After inoculation, the plants were left in a humid room at a room temperature of 20 to 23°C for about 24 hours to promote disease development. The degree of disease onset was investigated 6 to 10 days after inoculation, and the effectiveness of the drug solution was evaluated.

As a result, the compounds shown below showed a control value greater than 50%.
Compound number: A-001, A-002, A-003, A-004, A-005, A-006, A-008, A-009, A-010, A-012, A-013, A-014 , A-015, A-018, A-020, A-022, A-023, A-024, A-025, A-026, A-027, A-028, A-031, A-032, A -033, A-034, A-037, A-038, A-039, A-040, A-041, A-042, A-043, A-044, A-045, A-046, A-047 , A-048, A-049, A-050, A-052, A-053, A-055, A-056, A-057, A-058, A-059, A-061, A-063, A -064, A-065, A-067, A-068, A-069, A-070, A-071, A-072, A-073, A-074, A-075, A-076, A-077 , A-078, A-080, A-081, A-082, A-083, A-084, A-085, A-086, A-087, A-088, A-089, A-090, A -096, A-097, A-103, A-105

Next, a comparison of the bactericidal activity of Comparative Compound A and the compounds of the present invention (A-042, A-043, A-044, A-075, A-088) will be illustrated. Note that Comparative Compound A was synthesized by a method similar to Production Methods V and W using corresponding raw material compounds.

[Comparative Example 1] Cabbage black sooty blight A test for cabbage black sooty blight was conducted according to the method of Test Example C. The results are shown in Table 10.

Table 10 shows that the compounds of the present invention exhibit a more superior bactericidal effect than Comparative Compound A against cabbage black spot.

[Comparative Example 2] Barley powdery mildew test was conducted according to the method of Test Example D for barley powdery mildew. The results are shown in Table 11.

Table 11 shows that the compounds of the present invention exhibit a superior bactericidal effect than Comparative Compound A against barley powdery mildew.

[Comparative Example 3] Cucumber anthracnose A test for cucumber anthracnose was conducted according to the method of Test Example H. The results are shown in Table 12.

Table 12 shows that the compounds of the present invention exhibit superior bactericidal activity to cucumber anthracnose than Comparative Compound A.

Comparative Examples 1 to 3 show that the group of compounds into which a substituted pyrazole group is introduced is more effective at lower doses than the unsubstituted pyrazole group.

The compound of the present invention is a novel compound and can control plant diseases, so it has utility as an agricultural pesticide, for example, an agricultural and horticultural pest control agent, particularly an agricultural and horticultural fungicide.

The disclosure of Japanese Patent Application No. 2018-190615 (filing date: October 9, 2018) is incorporated herein by reference in its entirety.
All documents, patent applications, and technical standards mentioned herein are incorporated by reference to the same extent as if each individual document, patent application, and technical standard was specifically and individually indicated to be incorporated by reference. Incorporated herein by reference.

Claims (7)

Formula (1)

[In the formula,
R1 is
hydroxyl group,
cyano group,
C1 to C6 alkyl group which may be optionally substituted with substituent A,
C1 to C6 haloalkyl group,
C3 to C8 cycloalkyl group optionally substituted with substituent A,
C2 to C6 alkenyl group optionally substituted with substituent A,
C2-C6 haloalkenyl group,
C2 to C6 alkynyl group optionally substituted with substituent A,
C2-C6 haloalkynyl group,
C1 to C6 alkoxy group which may be optionally substituted with substituent A,
C1 to C6 haloalkoxy group,
C3 to C8 cycloalkoxy group which may be optionally substituted with substituent A,
C2 to C6 alkenyloxy group optionally substituted with substituent A,
C2-C6 haloalkenyloxy group,
a C3 to C6 alkynyloxy group which may be optionally substituted with substituent A;
C3 to C6 haloalkynyloxy group,
or RaRbN- (where Ra and Rb are each independently a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent B, a C1-C6 haloalkyl group, or a C3-C8 haloalkyl group) Ra and Rb represent a cycloalkyl group, or together with the nitrogen atom to which they are bonded, form an aziridinyl group, azetidinyl group, pyrrolidinyl group, piperidinyl group, morpholyl group, homopiperidinyl group, or azocanyl group .) represents;
R2 and R3 are each independent,
halogen atom,
hydroxyl group,
cyano group,
nitro group,
C1 to C6 alkyl group which may be optionally substituted with substituent C,
C1 to C6 haloalkyl group,
C3 to C8 cycloalkyl group which may be optionally substituted with substituent C,
C2 to C6 alkenyl group optionally substituted with substituent C,
C2-C6 haloalkenyl group,
a C2 to C6 alkynyl group which may be optionally substituted with substituent C;
C2-C6 haloalkynyl group,
C1 to C6 alkoxy group which may be optionally substituted with substituent C,
C1 to C6 haloalkoxy group,
C3 to C8 cycloalkoxy group which may be optionally substituted with substituent C,
C2 to C6 alkenyloxy group optionally substituted with substituent C,
C2-C6 haloalkenyloxy group,
a C3 to C6 alkynyloxy group which may be optionally substituted with substituent C;
C3 to C6 haloalkynyloxy group,
RdC(=O)-(wherein, Rd is a hydrogen atom, a C1 to C6 alkyl group which may be optionally substituted with substituent B, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group, a C1 to C8 cycloalkyl group, represents a C6 alkoxy group, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group, or RaRbN- (where Ra and Rb have the same meanings as above),
RdC(=O)O- (here, Rd has the same meaning as above),
Rc-L- (where Rc represents a C1 to C6 alkyl group or a C1 to C6 haloalkyl group, and L represents S, SO, or SO ₂ ),
RaRbN- (where Ra and Rb have the same meanings as above),
or ReC(=O)N(Rf)- (where Re is a hydrogen atom, a C1 to C6 alkyl group which may be optionally substituted with substituent B, a C1 to C6 haloalkyl group, a C3 to C8 cyclo Represents an alkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or RaRbN- (where Ra and Rb have the same meanings as above), and Rf is , represents a hydrogen atom, a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, or a C3 to C8 cycloalkyl group, which may be optionally substituted with a substituent B);
n represents an integer of 0 to 4 (when n is 2 or more, R3 of 2 or more substitutions each represents an independent substituent);
R4 is
halogen atom,
cyano group,
nitro group,
C1 to C6 alkyl group which may be optionally substituted with substituent A,
C1 to C6 haloalkyl group,
C3 to C8 cycloalkyl group optionally substituted with substituent A,
C2 to C6 alkenyl group optionally substituted with substituent A,
C2-C6 haloalkenyl group,
C2 to C6 alkynyl group optionally substituted with substituent A,
C2-C6 haloalkynyl group,
C1 to C6 alkoxy group which may be optionally substituted with substituent A,
C1 to C6 haloalkoxy group,
C3 to C8 cycloalkoxy group which may be optionally substituted with substituent A,
C2 to C6 alkenyloxy group optionally substituted with substituent A,
C2-C6 haloalkenyloxy group,
a C3 to C6 alkynyloxy group which may be optionally substituted with substituent A;
C3 to C6 haloalkynyloxy group,
Rc-L- (where Rc and L have the same meanings as above),
RaRbN- (where Ra and Rb have the same meanings as above),
or RgC(=O)- (where Rg is a hydrogen atom, a hydroxyl group, a C1 to C6 alkyl group that may be optionally substituted with substituent B, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group, represents a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group, or RaRbN- (where Ra and Rb have the same meanings as above);
R5 is
halogen atom,
cyano group,
nitro group,
C1 to C6 alkyl group which may be optionally substituted with substituent C,
C1 to C6 haloalkyl group,
C3 to C8 cycloalkyl group which may be optionally substituted with substituent C,
C2 to C6 alkenyl group optionally substituted with substituent C,
C2-C6 haloalkenyl group,
a C2 to C6 alkynyl group which may be optionally substituted with substituent C;
C2-C6 haloalkynyl group,
C1 to C6 alkoxy group which may be optionally substituted with substituent C,
C1 to C6 haloalkoxy group,
C3 to C8 cycloalkoxy group which may be optionally substituted with substituent C,
C2 to C6 alkenyloxy group optionally substituted with substituent C,
C2-C6 haloalkenyloxy group,
a C3 to C6 alkynyloxy group which may be optionally substituted with substituent C;
C3 to C6 haloalkynyloxy group,
RdC(=O)-(here, Rd has the same meaning as above),
RdC(=O)O- (here, Rd has the same meaning as above),
Rc-L- (where Rc and L have the same meanings as above),
RaRbN- (where Ra and Rb have the same meanings as above),
ReC(=O)N(Rf)-(Here, Re and Rf have the same meanings as above.),
RhON=C(Ri)- (where Rh and Ri each independently represent a hydrogen atom or a C1 to C6 alkyl group),
or a phenyl group that may be optionally substituted with 0 to 5 substituents D (however, in the case of two or more substituents D, each is independent);
m represents an integer of 1 to 2 (when m is 2, each of the two substituted R5s is independent);
X represents an oxygen atom or a sulfur atom;
Bonds containing broken lines represent double bonds or single bonds;
Substituent A 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- (where Rc and L are as defined above);
Substituent B is 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;
Substituent C is a hydroxyl group, a cyano group, a C3 to C8 cycloalkyl group, a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group, a C2 to C6 alkoxyalkoxy group, RaRbN -(Here, Ra and Rb have the same meanings as above.), Rc-L-(Here, Rc and L have the same meanings as above.), RdC(=O)-(Here, Rd is as defined above) and at least one member selected from the group consisting of a 3- to 6-membered ring group containing 1 to 2 oxygen atoms;
Substituent D is a hydroxyl group, a cyano group, a halogen atom, a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, a C1 to C6 alkoxy group, RaRbN- (where Ra and Rb are as defined above) ) and Rc-L- (where Rc and L have the same meanings as above). ] or its salt. R1 is
C1 to C6 alkyl group which may be optionally substituted with substituent A,
C1 to C6 haloalkyl group,
C2 to C6 alkenyl group optionally substituted with substituent A,
C2-C6 haloalkenyl group,
C1 to C6 alkoxy group which may be optionally substituted with substituent A,
or RaRbN- (where Ra and Rb are each independently a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent B, a C1-C6 haloalkyl group, or a C3-C8 haloalkyl group) Ra and Rb represent a cycloalkyl group, or together with the nitrogen atom to which they are bonded, form an aziridinyl group, azetidinyl group, pyrrolidinyl group, piperidinyl group, morpholyl group, homopiperidinyl group, or azocanyl group .) represents;
R2 and R3 are each independent,
halogen atom,
hydroxyl group,
cyano group,
C1 to C6 alkyl group which may be optionally substituted with substituent C,
C1 to C6 haloalkyl group,
C2 to C6 alkenyl group optionally substituted with substituent C,
a C2 to C6 alkynyl group which may be optionally substituted with substituent C;
C1 to C6 alkoxy group which may be optionally substituted with substituent C,
C1 to C6 haloalkoxy group,
C2 to C6 alkenyloxy group optionally substituted with substituent C,
a C3 to C6 alkynyloxy group which may be optionally substituted with substituent C;
or Rc-L- (where Rc represents a C1 to C6 alkyl group or a C1 to C6 haloalkyl group, and L represents S, SO, or SO ₂ );
R4 is
halogen atom,
C1 to C6 alkyl group which may be optionally substituted with substituent A,
C1 to C6 haloalkyl group,
C2 to C6 alkenyl group optionally substituted with substituent A,
C2 to C6 alkynyl group optionally substituted with substituent A,
C1 to C6 alkoxy group which may be optionally substituted with substituent A,
or RgC(=O)- (where Rg is a hydrogen atom, a hydroxyl group, a C1 to C6 alkyl group that may be optionally substituted with substituent B, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group, represents a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group, or RaRbN- (where Ra and Rb have the same meanings as above);
R5 is
halogen atom,
cyano group,
C1 to C6 alkyl group which may be optionally substituted with substituent C,
C1 to C6 haloalkyl group,
C3 to C8 cycloalkyl group which may be optionally substituted with substituent C,
C2 to C6 alkenyl group optionally substituted with substituent C,
C2-C6 haloalkenyl group,
a C2 to C6 alkynyl group which may be optionally substituted with substituent C;
C2-C6 haloalkynyl group,
C1 to C6 alkoxy group which may be optionally substituted with substituent C,
C2 to C6 alkenyloxy group optionally substituted with substituent C,
a C3 to C6 alkynyloxy group which may be optionally substituted with substituent C;
RdC(=O)-(wherein, Rd is a hydrogen atom, a C1 to C6 alkyl group which may be optionally substituted with substituent B, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group, a C1 to C8 cycloalkyl group, represents a C6 alkoxy group, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group, or RaRbN- (where Ra and Rb have the same meanings as above),
Rc-L- (where Rc and L have the same meanings as above),
RaRbN- (where Ra and Rb have the same meanings as above),
RhON=C(Ri)- (where Rh and Ri each independently represent a hydrogen atom or a C1 to C6 alkyl group),
or a phenyl group which may be optionally substituted with 0 to 5 substituents D (however, in the case of two or more substituents D, each is independent), or a salt thereof according to claim 1. . R1 is
C1 to C6 alkyl group which may be optionally substituted with substituent A,
or represents a C1 to C6 haloalkyl group;
R2 and R3 are each independent,
halogen atom,
C1 to C6 alkyl group which may be optionally substituted with substituent C,
C1 to C6 alkoxy group which may be optionally substituted with substituent C,
or Rc-L- (where Rc represents a C1 to C6 alkyl group or a C1 to C6 haloalkyl group, and L represents S, SO, or SO ₂ );
R4 is
Represents a halogen atom;
R5 is
halogen atom,
cyano group,
C1 to C6 alkyl group which may be optionally substituted with substituent C,
C1 to C6 haloalkyl group,
C3 to C8 cycloalkyl group which may be optionally substituted with substituent C,
C2 to C6 alkenyl group optionally substituted with substituent C,
a C2 to C6 alkynyl group which may be optionally substituted with substituent C;
C1 to C6 alkoxy group which may be optionally substituted with substituent C,
RdC(=O)-(wherein, Rd is a hydrogen atom, a C1 to C6 alkyl group which may be optionally substituted with substituent B, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group, a C1 to C8 cycloalkyl group, C6 alkoxy group, C1 to C6 haloalkoxy group, C3 to C8 cycloalkoxy group, or RaRbN- (where Ra and Rb are each independently substituted with a hydrogen atom or substituent B) may represent a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group, or Ra and Rb, together with the nitrogen atom to which they are bonded, represent an aziridinyl group, an azetidinyl group, represents a group that forms a pyrrolidinyl group, piperidinyl group, morpholyl group, homopiperidinyl group, or azocanyl group),
Rc-L- (where Rc and L have the same meanings as above),
RhON=C(Ri)- (where Rh and Ri each independently represent a hydrogen atom or a C1 to C6 alkyl group),
or a phenyl group which may be optionally substituted with 0 to 5 substituents D (however, in the case of two or more substituents D, each is independent),
X represents an oxygen atom,
3. The compound or a salt thereof according to claim 2, wherein the bond containing the broken line represents a double bond. An agricultural and horticultural pest control agent containing the compound according to claim 1 or a salt thereof as an active ingredient. An agricultural and 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 4 to plants, plant seeds, or soil in which plants are cultivated. A method for controlling plant diseases, which comprises applying the agricultural and horticultural fungicide according to claim 5 to plants, plant seeds, or soil in which plants are grown.