JP7118961B2 - Pyridone compound and agricultural and horticultural fungicide containing the same as an active ingredient - Google Patents

Description

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

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

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

WO 98/55480 EP 0308020 WO2016/12913

However, the uses of the compounds described in WO 98/55480, EP 0308020 and WO 2016/12913 are all related to medicine, and the agricultural and horticultural fungicide according to the present invention It is different from the technical field to which the agent belongs.

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

In order to solve the above-mentioned problems, the present inventors have made extensive studies on a group of 1,3,5,6-substituted-2-pyridone compounds. As a result, it was found that a novel compound group in which a substituent containing an oxime structure (C=N-O) was introduced at the 5-position in the 2-pyridone skeleton exhibited excellent control activity against plant diseases. , have completed the present invention.

［式中、Ｒ１は、
水酸基、
シアノ基、
置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
Ｃ１～Ｃ６のハロアルキル基、
置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
Ｃ２～Ｃ６のハロアルケニル基、
置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
Ｃ２～Ｃ６のハロアルキニル基、
置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
Ｃ１～Ｃ６のハロアルコキシ基、
置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、
置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニルオキシ基、
Ｃ２～Ｃ６のハロアルケニルオキシ基、
置換基Ａで適宜置換されてもよいＣ３～Ｃ６のアルキニルオキシ基、
Ｃ３～Ｃ６のハロアルキニルオキシ基、
またはＲａＲｂＮ－（ここで、ＲａおよびＲｂは、それぞれ独立していて、水素原子、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、またはＣ３～Ｃ８のシクロアルキル基を表すか、あるいはＲａおよびＲｂは、結合する窒素原子と一緒になって、アジリジニル基、アゼチジニル基、ピロリジニル基、ピペリジニル基、ホモピペリジニル基、またはアゾカニル基を形成するものを表す。）を表し；
Ｒ２は、
水素原子、
シアノ基、
ニトロ基、
ハロゲン原子、
置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
Ｃ１～Ｃ６のハロアルキル基、
置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
Ｃ２～Ｃ６のハロアルケニル基、
置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
Ｃ２～Ｃ６のハロアルキニル基、
置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
Ｃ１～Ｃ６のハロアルコキシ基、
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、前記と同義である）を表す。）を表し；
Ｘは、酸素原子または硫黄原子を表し；
Ｙは、
Ｒ３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Ｒ３の場合、それぞれ独立している。）、
Ｒ３で適宜０～４置換されてもよいピリジル基（ただし、２置換以上のＲ３の場合、それぞれ独立している。）、
Ｒ３で適宜０～３置換されてもよいピリダジニル基（ただし、２置換以上のＲ３の場合、それぞれ独立している。）、
Ｒ３で適宜０～３置換されてもよいピリミジニル基（ただし、２置換以上のＲ３の場合、それぞれ独立している。）、
Ｒ３で適宜０～３置換されてもよいピラジニル基（ただし、２置換以上のＲ３の場合、それぞれ独立している。）、
Ｒ３で適宜０～２置換されてもよいトリアジニル基（ただし、２置換のＲ３の場合、それぞれ独立している。）、
Ｒ３で適宜置換されてもよいテトラジニル基、
Ｒ３で適宜０～３置換されてもよいチエニル基（ただし、２置換以上のＲ３の場合、それぞれ独立している。）、
Ｒ３で適宜０～２置換されてもよいチアゾリル基（ただし、２置換のＲ３の場合、それぞれ独立している。）、
Ｒ３で適宜０～２置換されてもよいイソチアゾリル基（ただし、２置換のＲ３の場合、それぞれ独立している。）、
またはＲ３で適宜置換されてもよいチアジアゾリル基を表し、
Ｒ３は、
水酸基、
シアノ基、
ニトロ基、
ハロゲン原子、
置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
Ｃ１～Ｃ６のハロアルキル基、
置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
Ｃ２～Ｃ６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。）、
１～２個の酸素原子を含む３～６員環の基、
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ＲｅＣ（＝Ｏ）Ｎ（Ｒｆ）－（ここで、ＲｅとＲｆは、それぞれ独立していて、水素原子、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、またはＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）を表す。）を表し；
Ｒ４は、
水素原子、
置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
Ｃ１～Ｃ６のハロアルキル基、
置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
Ｃ２～Ｃ６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。）、
置換基Ｄで適宜０～５置換されてもよいフェニル基を有するＣ１～Ｃ６のアルキル基（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。）、
置換基Ｄで適宜０～５置換されてもよいフェニル基を有するＣ１～Ｃ６のハロアルキル基（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。）、
またはＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）を表し、
Ｒ５は、
水素原子、
置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
Ｃ１～Ｃ６のハロアルキル基、
置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
Ｃ２～Ｃ６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。）、
置換基Ｄで適宜０～５置換されてもよいフェニル基を有するＣ１～Ｃ６のアルキル基（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。）、
置換基Ｄで適宜０～５置換されてもよいフェニル基を有するＣ１～Ｃ６のハロアルキル基（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。）、
またはＲｄＣ（＝Ｏ）－（ここで、Ｒｄは、前記と同義である。）を表し、
あるいは、Ｒ４とＲ５が、結合するオキシム構造（Ｃ＝Ｎ－Ｏ）と一緒になって、
置換基Ｅで適宜０～２置換されてもよいイソキサゾール環（ただし、２置換の置換基Ｅの場合、それぞれ独立している。）、
置換基Ｆで適宜０～４置換されてもよいイソキサゾリン環（ただし、２置換以上の置換基Ｆの場合、それぞれ独立している。）、
置換基Ｄで適宜０～４置換されてもよいベンズイソキサゾール環（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。）、
または置換基Ｆで適宜０～６置換されてもよい５，６－ジヒドロ－４Ｈ－１，２－オキサジン環（ただし、２置換以上の置換基Ｆの場合、それぞれ独立している。）を形成するものを表し；
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。）、ＲｄＣ（＝Ｏ）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、ニトロ基、ハロゲン原子、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Ｅは、水酸基、シアノ基、ハロゲン原子、置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ｃで適宜置換されてもよいＣ２～Ｃ６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、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。）、ＲｄＣ（＝Ｏ）Ｏ－（ここで、Ｒｄは、前記と同義である。）、ＲｇＯＮ＝Ｃ（Ｒｈ）－（ここで、ＲｇおよびＲｈ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。）、ＲｉＲｊＲｋＳｉ－（ここで、Ｒｉ、ＲｊおよびＲｋは、それぞれ独立していてＣ１～Ｃ６のアルキル基を表す。）および１～２個の酸素原子を含む３～６員環の基からなる群から選択される少なくとも１種であり；
置換基Ｆは、水酸基、シアノ基、ハロゲン原子、置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ｃで適宜置換されてもよいＣ２～Ｃ６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、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ＲｄＣ（＝Ｏ）Ｏ－（ここで、Ｒｄ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；
Ｒ２は、
水素原子、
ハロゲン原子、
置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
Ｃ１～Ｃ６のハロアルキル基、
置換基Ａで適宜置換されてもよい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、
Ｃ１～Ｃ６のハロアルコキシ基、
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。）、
または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、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。）を表し；
Ｙは、
Ｒ３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Ｒ３の場合、それぞれ独立している。）、
またはＲ３で適宜０～４置換されてもよいピリジル基（ただし、２置換以上のＲ３の場合、それぞれ独立している。）を表し、
Ｒ３は、
水酸基、
シアノ基、
ハロゲン原子、
置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
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、
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、
またはＲｄＣ（＝Ｏ）Ｏ－（ここで、Ｒｄは、前記と同義である。）を表し；
Ｒ４は、
水素原子、
置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
Ｃ１～Ｃ６のハロアルキル基、
置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
Ｃ２～Ｃ６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。）、
またはＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）を表し、
Ｒ５は、
水素原子、
置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
Ｃ１～Ｃ６のハロアルキル基、
置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
Ｃ２～Ｃ６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、
またはＲｄＣ（＝Ｏ）－（ここで、Ｒｄは、前記と同義である。）を表し、
あるいは、Ｒ４とＲ５が、結合するオキシム構造（Ｃ＝Ｎ－Ｏ）と一緒になって、
置換基Ｅで適宜０～２置換されてもよいイソキサゾール環（ただし、２置換の置換基Ｅの場合、それぞれ独立している。）、
置換基Ｆで適宜０～４置換されてもよいイソキサゾリン環（ただし、２置換以上の置換基Ｆの場合、それぞれ独立している。）、
または置換基Ｄで適宜０～４置換されてもよいベンズイソキサゾール環（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。）を形成するものを表す、［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、
置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
または置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基を表し；
Ｙは、
Ｒ３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Ｒ３の場合、それぞれ独立している。）を表し、
Ｒ３は、
シアノ基、
ハロゲン原子、
または置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基を表し；
Ｒ４は、
水素原子、
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Ｃ３～Ｃ８のシクロアルキル基、
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。）、
またはＲａＲｂＮ－（ここで、ＲａおよびＲｂは、それぞれ独立していて、水素原子、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、またはＣ３～Ｃ８のシクロアルキル基を表すか、あるいはＲａおよびＲｂは、結合する窒素原子と一緒になって、アジリジニル基、アゼチジニル基、ピロリジニル基、ピペリジニル基、ホモピペリジニル基、またはアゾカニル基を形成するものを表す。）を表し、
Ｒ５は、
水素原子、
置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
または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、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。）を表し、
あるいは、Ｒ４とＲ５が、結合するオキシム構造（Ｃ＝Ｎ－Ｏ）と一緒になって、
置換基Ｅで適宜０～２置換されてもよいイソキサゾール環（ただし、２置換の置換基Ｅの場合、それぞれ独立している。）、
置換基Ｆで適宜０～４置換されてもよいイソキサゾリン環（ただし、２置換以上の置換基Ｆの場合、それぞれ独立している。）、
または置換基Ｄで適宜０～４置換されてもよいベンズイソキサゾール環（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。）を形成するものを表す、［２］に記載の化合物またはその塩。
［４］
Ｒ４は、
水素原子、
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Ｃ３～Ｃ８のシクロアルキル基、
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。）、
またはＲａＲｂＮ－（ここで、ＲａおよびＲｂは、それぞれ独立していて、水素原子、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、またはＣ３～Ｃ８のシクロアルキル基を表すか、あるいはＲａおよびＲｂは、結合する窒素原子と一緒になって、アジリジニル基、アゼチジニル基、ピロリジニル基、ピペリジニル基、ホモピペリジニル基、またはアゾカニル基を形成するものを表す。）を表し、
Ｒ５は、
水素原子、
置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
または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、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。）を表し、
あるいは、Ｒ４とＲ５が、結合するオキシム構造（Ｃ＝Ｎ－Ｏ）と一緒になって、
置換基Ｅで適宜０～２置換されてもよいイソキサゾール環（ただし、２置換の置換基Ｅの場合、それぞれ独立している。）を形成するものを表す、［３］に記載の化合物またはその塩。
［５］
Ｒ１が、メチル基、エチル基、または２，２－ジフルオロエチル基である、［１］～［４］のいずれか１つに記載の化合物またはその塩。
［６］
Ｒ２が、塩素原子、臭素原子、メチル基、メトキシ基、またはエチニル基である、［１］～［５］のいずれか１つに記載の化合物またはその塩。
［７］
Ｘが、酸素原子である、［１］～［６］のいずれか１つに記載の化合物またはその塩。
［８］
Ｒ３が、シアノ基、フッ素原子、臭素原子、またはメトキシ基である、［１］～［７］のいずれか１つに記載の化合物またはその塩。
［９］
Ｙは、フェニル基、４－シアノフェニル基、４－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、２，６－ジフルオロ－４－メトキシフェニル基、３－ブロモ－４－メトキシフェニル基、または４－メトキシフェニル基である、［１］～［７］のいずれか１つに記載の化合物またはその塩。
［１０］
Ｒ４は、水素原子、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ｔ－ブチル基、シクロペンチル基、フェニル基、アミノ基、またはメチルアミノ基である、［１］～［９］のいずれか１つに記載の化合物またはその塩。
［１１］
Ｒ５は、水素原子、メチル基、エチル基、イソプロピル基、またはアセチル基である、［１］～［１０］のいずれか１つに記載の化合物またはその塩。
［１２］
Ｒ５ＯＮ＝Ｃ（Ｒ４）－の構造が、（ヒドロキシイミノ）メチル基、１－（ヒドロキシイミノ）プロピル基、１－（ヒドロキシイミノ）－２－メチルプロピル基、１－（ヒドロキシイミノ）－２，２－ジメチルプロピル基、１－（ヒドロキシイミノ）－３－メチルブチル基、（メトキシイミノ）メチル基、１－（メトキシイミノ）エチル基、１－（メトキシイミノ）プロピル基、１－（メトキシイミノ）－２－メチルプロピル基、１－（メトキシイミノ）－２，２－ジメチルプロピル基、１－（メトキシイミノ）ブチル基、１－（メトキシイミノ）－３－メチルブチル基、１－（メトキシイミノ）ペンチル基、（メトキシイミノ）（フェニル）メチル基、１－（エトキシイミノ）プロピル基、１－（イソプロピルオキシイミノ）プロピル基、１－（アセトキシイミノ）プロピル基、シクロペンチル（ヒドロキシイミノ）メチル基、シクロペンチル（メトキシイミノ）メチル基、ＨＯＮ＝Ｃ（ＮＨ２）－、ＨＯＮ＝Ｃ（ＮＨＭｅ）－、またはＭｅＯＮ＝Ｃ（ＮＨＭｅ）－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］
置換基Ｅが、ハロゲン原子、置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ｃで適宜置換されてもよいＣ２～Ｃ６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、ＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）、ＲｄＣ（＝Ｏ）－（ここで、Ｒｄは、前記と同義である。）、ＲｇＯＮ＝Ｃ（Ｒｈ）－（ここで、ＲｇおよびＲｈは、前記と同義である。）およびＲｉＲｊＲｋＳｉ－（ここで、Ｒｉ、ＲｊおよびＲｋ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、［１］～［９］のいずれか１つに記載の化合物またはその塩。
［１４］
置換基Ｅが、塩素原子、臭素原子、ヨウ素原子、メチル基、エチル基、イソプロピル基、ヒドロキシメチル基、１－ヒドロキシエチル基、トリフルオロアセトキシメチル基、ブロモメチル基、ジフルオロメチル基、ビニル基、エチニル基、アミノ基、ホルミル基、アセチル基、（メトキシイミノ）メチル基、およびトリメチルシリル基からなる群から選択される少なくとも１種である、［１］～［９］のいずれか１つに記載の化合物またはその塩。
［１５］
Ｒ４とＲ５が、結合するオキシム構造（Ｃ＝Ｎ－Ｏ）と一緒になって、置換基Ｅで適宜０～２置換されてもよいイソキサゾール環（ただし、２置換の置換基Ｅの場合、それぞれ独立している。）を形成するものが、イソキサゾール－３－イル基、４－クロロイソキサゾール－３－イル基、４－ブロモイソキサゾール－３－イル基、４－ヨードイソキサゾール－３－イル基、４－メチルイソキサゾール－３－イル基、５－メチルイソキサゾール－３－イル基、５－（ヒドロキシメチル）イソキサゾール－３－イル基、５－エチルイソキサゾール－３－イル基、５－（１－ヒドロキシエチル）イソキサゾール－３－イル基、５－イソプロピルイソキサゾール－３－イル基、５－アミノイソキサゾール－３－イル基、５－（トリメチルシリル）イソキサゾール－３－イル基、４，５－ジクロロイソキサゾール－３－イル基、４－クロロ－５－メチルイソキサゾール－３－イル基、４，５－ジブロモイソキサゾール－３－イル基、４－ブロモ－５－メチルイソキサゾール－３－イル基、４－ブロモ－５－エチルイソキサゾール－３－イル基、４－ブロモ－５－イソプロピルイソキサゾール－３－イル基、４－ブロモ－５－（ジフルオロメチル）イソキサゾール－３－イル基、４－ブロモ－５－ホルミルイソキサゾール－３－イル基、４－ブロモ－５－（トリメチルシリル）イソキサゾール－３－イル基、４，５－ジヨードイソキサゾール－３－イル基、４－ヨード－５－メチルイソキサゾール－３－イル基、４，５－ジメチルイソキサゾール－３－イル基、４－（ヒドロキシメチル）－５－メチルイソキサゾール－３－イル基、４－（ジフルオロメチル）－５－メチルイソキサゾール－３－イル基、４－（ブロモメチル）－５－メチルイソキサゾール－３－イル基、４－（トリフルオロアセトキシメチル）－５－メチルイソキサゾール－３－イル基、４－（１－ヒドロキシエチル）－５－メチルイソキサゾール－３－イル基、５－メチル－４－ビニルイソキサゾール－３－イル基、４－エチニル－５－メチルイソキサゾール－３－イル基、４－ホルミル－５－メチルイソキサゾール－３－イル基、４－アセチル－５－メチルイソキサゾール－３－イル基、または４－（（メトキシイミノ）メチル）－５－メチルイソキサゾール－３－イル基である［１］～［９］のいずれか１つに記載の化合物またはその塩。
［１６］
置換基Ｆが、ハロゲン原子、置換基Ｃで適宜置換されてもよいアルキル基、および置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基からなる群から選択される少なくとも１種である、［１］～［３］、［５］～［９］のいずれか１つに記載の化合物またはその塩。
［１７］
置換基Ｆが、臭素原子、メチル基、エチル基、およびエトキシ基からなる群から選択される少なくとも１種である、［１］～［３］、［５］～［９］のいずれか１つに記載の化合物またはその塩。
［１８］
Ｒ４とＲ５が、結合するオキシム構造（Ｃ＝Ｎ－Ｏ）と一緒になって、置換基Ｆで適宜０～４置換されてもよいイソキサゾリン環（ただし、２置換以上の置換基Ｆの場合、それぞれ独立している。）を形成するものが、４－ブロモ－５，５－ジメチル－４，５－ジヒドロイソキサゾール－３－イル基、５－エチル－４，５－ジヒドロイソキサゾール－３－イル基、５，５－ジメチル－４，５－ジヒドロイソキサゾール－３－イル基、または５－エトキシ－４，５－ジヒドロイソキサゾール－３－イル基である、［１］～［３］、［５］～［９］のいずれか１つに記載の化合物またはその塩。
［１９］
Ｒ４とＲ５が、結合するオキシム構造（Ｃ＝Ｎ－Ｏ）と一緒になって、置換基Ｄで適宜０～４置換されてもよいベンズイソキサゾール環（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。）を形成するものが、ベンゾ［ｄ］イソキサゾール－３－イル基である、［１］～［３］、［５］～［９］のいずれか１つに記載の化合物またはその塩。
［２０］
［１］～［１９］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。
［２１］
［１］～［１９］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。
［２２］
［２０］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。
［２３］
［２１］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。That is, the present invention is as follows.
[1]
formula (1)

[In the formula, R is
hydroxyl group,
cyano group,
a C1-C6 alkyl group optionally substituted with a substituent A,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with a substituent A,
a C2-C6 alkenyl group optionally substituted with a substituent A,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted with a substituent A,
a C2-C6 haloalkynyl group,
a C1-C6 alkoxy group optionally substituted with a substituent A,
a C1-C6 haloalkoxy group,
a C3-C8 cycloalkoxy group optionally substituted with a substituent A;
a C2-C6 alkenyloxy group optionally substituted with a substituent A,
a C2-C6 haloalkenyloxy group,
a C3-C6 alkynyloxy group optionally substituted with a substituent A,
a C3-C6 haloalkynyloxy group,
or RaRbN- (wherein Ra and Rb are each independently a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, or a C3-C8 Alternatively, Ra and Rb together with the attached nitrogen atom form an aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl, homopiperidinyl, or azocanyl group). represent;
R2 is
hydrogen atom,
cyano group,
nitro group,
halogen atom,
a C1-C6 alkyl group optionally substituted with a substituent A,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with a substituent A,
a C2-C6 alkenyl group optionally substituted with a substituent A,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted with a substituent A,
a C2-C6 haloalkynyl group,
a C1-C6 alkoxy group optionally substituted with a substituent A,
a C1-C6 haloalkoxy group,
a C3-C8 cycloalkoxy group optionally substituted with a substituent A;
a C2-C6 alkenyloxy group optionally substituted with a substituent A,
a C2-C6 haloalkenyloxy group,
a C3-C6 alkynyloxy group optionally substituted with a substituent A,
a C3-C6 haloalkynyloxy group,
Rc-L- (wherein Rc represents a C1-C6 alkyl group or a C1 _- C6 haloalkyl group, and L represents S, SO, or SO2),
RaRbN- (wherein Ra and Rb are as defined above),
or RdC(=O)-(wherein Rd is a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, C1 represents a C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or RaRbN- (wherein the same definition as above);
X represents an oxygen atom or a sulfur atom;
Y is
a phenyl group optionally substituted with 0 to 5 substituents with R3 (however, in the case of disubstituted or more R3, each is independent),
a pyridyl group optionally substituted with 0 to 4 substituents with R3 (provided that, in the case of two or more substituted R3, each is independent),
a pyridazinyl group optionally substituted by R3 with 0 to 3 substituents (provided that, in the case of two or more substituted R3, each is independent),
a pyrimidinyl group optionally substituted with 0 to 3 substituents with R3 (provided that, in the case of two or more substituted R3, each is independent),
a pyrazinyl group optionally substituted by R3 with 0 to 3 substituents (provided that, in the case of two or more substituted R3, each is independent),
a triazinyl group optionally substituted with 0 to 2 substituents with R3 (provided that, in the case of disubstituted R3, each is independent),
a tetrazinyl group optionally substituted with R3,
a thienyl group which may be optionally substituted with 0 to 3 substituents with R3 (provided, however, that each R3 is independently substituted with 2 or more substituents),
a thiazolyl group optionally substituted with 0 to 2 substituents at R3 (provided that, in the case of disubstituted R3, each is independent),
an isothiazolyl group optionally substituted with 0 to 2 substituents at R3 (provided, however, that in the case of disubstituted R3, each is independent),
or represents a thiadiazolyl group optionally substituted with R3,
R3 is
hydroxyl group,
cyano group,
nitro group,
halogen atom,
a C1 to C6 alkyl group optionally substituted with a substituent C,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with a substituent C,
a C2-C6 alkenyl group optionally substituted with a substituent C,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted with a substituent C,
a C2-C6 haloalkynyl group,
a C1-C6 alkoxy group optionally substituted with a substituent C,
a C1-C6 haloalkoxy group,
a C3-C8 cycloalkoxy group optionally substituted with a substituent C,
a C2-C6 alkenyloxy group optionally substituted with a substituent C,
a C2-C6 haloalkenyloxy group,
a C3-C6 alkynyloxy group optionally substituted with a substituent C,
a C3-C6 haloalkynyloxy group,
RdC (=O) - (wherein Rd is as defined above),
RdC(=O)O- (wherein Rd is as defined above),
a 3- to 6-membered ring group containing 1 to 2 oxygen atoms;
Rc-L- (wherein Rc and L are as defined above),
RaRbN- (wherein Ra and Rb are as defined above),
or ReC(=O)N(Rf)- (where Re and Rf are each independently a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 A haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or RaRbN— (wherein Ra and Rb are There is.) Represents.) Represents;
R4 is
hydrogen atom,
a C1 to C6 alkyl group optionally substituted with a substituent C,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with a substituent C,
a C2-C6 alkenyl group optionally substituted with a substituent C,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted with a substituent C,
a C2-C6 haloalkynyl group,
a phenyl group optionally substituted with 0 to 5 substituents D (provided that, in the case of disubstituted or more substituents D, each is independent),
a C1-C6 alkyl group having a phenyl group optionally substituted with 0 to 5 substituents D (provided that, in the case of disubstituted or more substituents D, each is independent);
a C1-C6 haloalkyl group having a phenyl group optionally substituted with 0 to 5 substituents D (provided that, in the case of disubstituted or more substituents D, each is independent);
or RaRbN- (wherein Ra and Rb are as defined above),
R5 is
hydrogen atom,
a C1 to C6 alkyl group optionally substituted with a substituent C,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with a substituent C,
a C2-C6 alkenyl group optionally substituted with a substituent C,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted with a substituent C,
a C2-C6 haloalkynyl group,
a phenyl group optionally substituted with 0 to 5 substituents D (provided that, in the case of disubstituted or more substituents D, each is independent),
a C1-C6 alkyl group having a phenyl group optionally substituted with 0 to 5 substituents D (provided that, in the case of disubstituted or more substituents D, each is independent);
a C1-C6 haloalkyl group having a phenyl group optionally substituted with 0 to 5 substituents D (provided that, in the case of disubstituted or more substituents D, each is independent);
or RdC (=O) - (wherein Rd is as defined above),
Alternatively, R4 and R5, together with the attached oxime structure (C=N-O),
an isoxazole ring optionally substituted with 0 to 2 substituents E (provided that, in the case of disubstituted substituents E, each is independent),
an isoxazoline ring optionally substituted with 0 to 4 substituents F (provided that, in the case of two or more substituents F, each is independent),
a benzisoxazole ring optionally substituted with 0 to 4 substituents D (provided that, in the case of two or more substituents D, each is independent);
Alternatively, a 5,6-dihydro-4H-1,2-oxazine ring optionally substituted with 0 to 6 substituents F (provided that, in the case of 2 or more substituents F, each is independent) is formed. represents what to do;
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- (wherein Rc and L are as defined above); at least one selected from the group consisting of;
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-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, a C2-C6 alkoxyalkoxy group, RaRbN. - (where Ra and Rb are as defined above), Rc-L- (wherein Rc and L are as defined above), RdC (=O) - (where Rd is as defined above), RdC(=O)O— (wherein Rd is as defined above) and a 3- to 6-membered ring group containing 1 to 2 oxygen atoms is at least one selected from the group;
Substituent D is a hydroxyl group, a cyano group, a nitro group, a halogen atom, a C1 to C6 alkyl group optionally substituted with a substituent B, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group, a C1 to at least one selected from the group consisting of a C6 alkoxy group, a C1-C6 haloalkoxy group and a C3-C8 cycloalkoxy group;
Substituent E is a hydroxyl group, a cyano group, a halogen atom, a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group, a C3-C8 optionally substituted with a substituent C A 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, a C2-C6 haloalkynyl group, C1-C6 alkoxy group optionally substituted with substituent C, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group optionally substituted with substituent C, substituent C C2-C6 alkenyloxy group optionally substituted with C2-C6 haloalkenyloxy group, C3-C6 alkynyloxy group optionally substituted with substituent C, C3-C6 haloalkynyloxy group , a C2-C6 alkoxyalkoxy group, RaRbN- (where Ra and Rb are as defined above), Rc-L- (wherein Rc and L are as defined above), RdC (=O)-(wherein Rd is as defined above), RdC(=O)O-(wherein Rd is as defined above), RgON=C(Rh)-( Here, Rg and Rh each independently represent a hydrogen atom or a C1-C6 alkyl group.), RiRjRkSi- (wherein Ri, Rj and Rk each independently represent a C1-C6 represents an alkyl group) and at least one selected from the group consisting of a 3- to 6-membered ring group containing 1 to 2 oxygen atoms;
Substituent F is a hydroxyl group, a cyano group, a halogen atom, a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group, a C3-C8 optionally substituted with a substituent C A 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, a C2-C6 haloalkynyl group, C1-C6 alkoxy group optionally substituted with substituent C, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group optionally substituted with substituent C, substituent C C2-C6 alkenyloxy group optionally substituted with C2-C6 haloalkenyloxy group, C3-C6 alkynyloxy group optionally substituted with substituent C, C3-C6 haloalkynyloxy group , RaRbN- (wherein Ra and Rb are as defined above), Rc-L- (wherein Rc and L are as defined above), RdC (=O)- (where , Rd has the same meaning as defined above) and RdC(=O)O- (wherein Rd has the same meaning as defined above). ] or a salt thereof.
[2]
R1 is
a C1-C6 alkyl group optionally substituted with a substituent A,
a C1-C6 haloalkyl group,
a C2-C6 alkenyl group optionally substituted with a substituent A,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted with a substituent A,
or represents a C2-C6 haloalkynyl group;
R2 is
hydrogen atom,
halogen atom,
a C1-C6 alkyl group optionally substituted with a substituent A,
a C1-C6 haloalkyl group,
a C2-C6 alkenyl group optionally substituted with a substituent A,
a C2-C6 alkynyl group optionally substituted with a substituent A,
a C1-C6 alkoxy group optionally substituted with a substituent A,
a C1-C6 haloalkoxy group,
Rc-L- (wherein Rc represents a C1-C6 alkyl group or a C1 _- C6 haloalkyl group, and L represents S, SO, or SO2),
or RdC(=O)-(wherein Rd is a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, C1 ~C6 alkoxy group, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group, or RaRbN- (wherein Ra and Rb are each independently and optionally substituted with a hydrogen atom, a substituent B may be a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group, or Ra and Rb together with the binding nitrogen atom are an aziridinyl group, an azetidinyl , represents a pyrrolidinyl group, a piperidinyl group, a homopiperidinyl group, or an azocanyl group.) represents;
Y is
a phenyl group optionally substituted with 0 to 5 substituents with R3 (however, in the case of disubstituted or more R3, each is independent),
or R3 optionally represents a pyridyl group optionally substituted with 0 to 4 substituents (provided that, in the case of two or more substituted R3, each is independent),
R3 is
hydroxyl group,
cyano group,
halogen atom,
a C1 to C6 alkyl group optionally substituted with a substituent C,
a C1-C6 alkoxy group optionally substituted with a substituent C,
a C1-C6 haloalkoxy group,
a C2-C6 alkenyloxy group optionally substituted with a substituent C,
a C2-C6 haloalkenyloxy group,
a C3-C6 alkynyloxy group optionally substituted with a substituent C,
a C3-C6 haloalkynyloxy group,
or RdC (=O) O- (wherein Rd is as defined above);
R4 is
hydrogen atom,
a C1 to C6 alkyl group optionally substituted with a substituent C,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with a substituent C,
a C2-C6 alkenyl group optionally substituted with a substituent C,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted with a substituent C,
a C2-C6 haloalkynyl group,
a phenyl group optionally substituted with 0 to 5 substituents D (provided that, in the case of disubstituted or more substituents D, each is independent),
or RaRbN- (wherein Ra and Rb are as defined above),
R5 is
hydrogen atom,
a C1 to C6 alkyl group optionally substituted with a substituent C,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with a substituent C,
a C2-C6 alkenyl group optionally substituted with a substituent C,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted with a substituent C,
a C2-C6 haloalkynyl group,
or RdC (=O) - (wherein Rd is as defined above),
Alternatively, R4 and R5, together with the attached oxime structure (C=N-O),
an isoxazole ring optionally substituted with 0 to 2 substituents E (provided that, in the case of disubstituted substituents E, each is independent),
an isoxazoline ring optionally substituted with 0 to 4 substituents F (provided that, in the case of two or more substituents F, each is independent),
or a benzisoxazole ring optionally substituted with 0 to 4 substituents D (provided that, in the case of disubstituted or more substituents D, each is independent), [1] The described compound or a salt thereof.
[3]
R1 is
a C1-C6 alkyl group optionally substituted with a substituent A,
or represents a C1-C6 haloalkyl group;
R2 is
halogen atom,
a C1-C6 alkyl group optionally substituted with a substituent A,
a C2-C6 alkynyl group optionally substituted with a substituent A,
or represents a C1-C6 alkoxy group optionally substituted with a substituent A;
Y is
a phenyl group optionally substituted with 0 to 5 substituents at R3 (provided, however, that each R3 is disubstituted or more is independent);
R3 is
cyano group,
halogen atom,
or represents a C1-C6 alkoxy group optionally substituted with a substituent C;
R4 is
hydrogen atom,
a C1 to C6 alkyl group optionally substituted with a substituent C,
a C3-C8 cycloalkyl group optionally substituted with a substituent C,
a phenyl group optionally substituted with 0 to 5 substituents D (provided that, in the case of disubstituted or more substituents D, each is independent),
or RaRbN- (wherein Ra and Rb are each independently a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, or a C3-C8 Alternatively, Ra and Rb together with the attached nitrogen atom form an aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl, homopiperidinyl, or azocanyl group). represent,
R5 is
hydrogen atom,
a C1 to C6 alkyl group optionally substituted with a substituent C,
or RdC(=O)-(wherein Rd is a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, C1 ~C6 alkoxy group, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group, or RaRbN- (wherein Ra and Rb are each independently and optionally substituted with a hydrogen atom, a substituent B may be a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group, or Ra and Rb together with the binding nitrogen atom are an aziridinyl group, an azetidinyl , a pyrrolidinyl group, a piperidinyl group, a homopiperidinyl group, or an azocanyl group.
Alternatively, R4 and R5, together with the attached oxime structure (C=N-O),
an isoxazole ring optionally substituted with 0 to 2 substituents E (provided that, in the case of disubstituted substituents E, each is independent),
an isoxazoline ring optionally substituted with 0 to 4 substituents F (provided that, in the case of two or more substituents F, each is independent),
or a benzisoxazole ring optionally substituted with 0 to 4 substituents D (provided that, in the case of disubstituted or more substituents D, each is independent), [2] The described compound or a salt thereof.
[4]
R4 is
hydrogen atom,
a C1 to C6 alkyl group optionally substituted with a substituent C,
a C3-C8 cycloalkyl group optionally substituted with a substituent C,
a phenyl group optionally substituted with 0 to 5 substituents D (provided that, in the case of disubstituted or more substituents D, each is independent),
or RaRbN- (wherein Ra and Rb are each independently a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, or a C3-C8 Alternatively, Ra and Rb together with the attached nitrogen atom form an aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl, homopiperidinyl, or azocanyl group). represent,
R5 is
hydrogen atom,
a C1 to C6 alkyl group optionally substituted with a substituent C,
or RdC(=O)-(wherein Rd is a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, C1 ~C6 alkoxy group, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group, or RaRbN- (wherein Ra and Rb are each independently and optionally substituted with a hydrogen atom, a substituent B may be a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group, or Ra and Rb together with the binding nitrogen atom are an aziridinyl group, an azetidinyl , a pyrrolidinyl group, a piperidinyl group, a homopiperidinyl group, or an azocanyl group.
Alternatively, R4 and R5, together with the attached oxime structure (C=N-O),
The compound according to [3] or its salt.
[5]
The compound or salt thereof according to any one of [1] to [4], wherein R1 is a methyl group, an ethyl group, or a 2,2-difluoroethyl group.
[6]
The compound or salt thereof according to any one of [1] to [5], wherein R2 is a chlorine atom, a bromine atom, a methyl group, a methoxy group, or an ethynyl group.
[7]
The compound or salt thereof according to any one of [1] to [6], wherein X is an oxygen atom.
[8]
The compound or salt thereof according to any one of [1] to [7], wherein R3 is a cyano group, a fluorine atom, a bromine atom, or a methoxy group.
[9]
Y is a phenyl group, 4-cyanophenyl group, 4-fluorophenyl group, 2,6-difluorophenyl group, 2,4,6-trifluorophenyl group, 2,6-difluoro-4-methoxyphenyl group, 3 The compound or salt thereof according to any one of [1] to [7], which is -bromo-4-methoxyphenyl group or 4-methoxyphenyl group.
[10]
R4 is a hydrogen atom, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, cyclopentyl group, phenyl group, amino group, or methylamino group, [1]-[ 9], the compound or a salt thereof according to any one of the above.
[11]
The compound or salt thereof according to any one of [1] to [10], wherein R5 is a hydrogen atom, a methyl group, an ethyl group, an isopropyl group, or an acetyl group.
[12]
The structure of R5ON=C(R4)- is a (hydroxyimino)methyl group, 1-(hydroxyimino)propyl group, 1-(hydroxyimino)-2-methylpropyl group, 1-(hydroxyimino)-2,2 -dimethylpropyl group, 1-(hydroxyimino)-3-methylbutyl group, (methoxyimino)methyl group, 1-(methoxyimino)ethyl group, 1-(methoxyimino)propyl group, 1-(methoxyimino)-2 -methylpropyl group, 1-(methoxyimino)-2,2-dimethylpropyl group, 1-(methoxyimino)butyl group, 1-(methoxyimino)-3-methylbutyl group, 1-(methoxyimino)pentyl group, (Methoxyimino) (phenyl) methyl group, 1-(ethoxyimino) propyl group, 1-(isopropyloxyimino) propyl group, 1-(acetoxyimino) propyl group, cyclopentyl (hydroxyimino) methyl group, cyclopentyl (methoxyimino) ) a methyl group, HON=C(NH2)-, HON=C(NHMe)-, or MeON=C(NHMe)-, the compound or a salt thereof according to any one of [1] to [9] .
[13]
Substituent E is a halogen atom, a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group, a C2-C6 alkenyl group optionally substituted with a substituent C, a substituent C2-C6 alkynyl group optionally substituted with C, RaRbN- (wherein Ra and Rb are as defined above), RdC(=O)- (wherein Rd is as defined above ), RgON=C(Rh)- (wherein Rg and Rh are as defined above) and RiRjRkSi- (wherein Ri, Rj and Rk are as defined above) from The compound or salt thereof according to any one of [1] to [9], which is at least one selected from the group consisting of:
[14]
Substituent E is chlorine atom, bromine atom, iodine atom, methyl group, ethyl group, isopropyl group, hydroxymethyl group, 1-hydroxyethyl group, trifluoroacetoxymethyl group, bromomethyl group, difluoromethyl group, vinyl group, ethynyl The compound according to any one of [1] to [9], which is at least one selected from the group consisting of an amino group, a formyl group, an acetyl group, a (methoxyimino)methyl group, and a trimethylsilyl group. Or its salt.
[15]
Together with the oxime structure (C═N—O) to which R4 and R5 are attached, an isoxazole ring optionally substituted with 0 to 2 substituents E (however, in the case of a disubstituted substituent E, each are independent) are formed by isoxazol-3-yl group, 4-chloroisoxazol-3-yl group, 4-bromoisoxazol-3-yl group, 4-iodoisoxazol- 3-yl group, 4-methylisoxazol-3-yl group, 5-methylisoxazol-3-yl group, 5-(hydroxymethyl)isoxazol-3-yl group, 5-ethylisoxazol-3 -yl group, 5-(1-hydroxyethyl)isoxazol-3-yl group, 5-isopropylisoxazol-3-yl group, 5-aminoisoxazol-3-yl group, 5-(trimethylsilyl)isoxazol- 3-yl group, 4,5-dichloroisoxazol-3-yl group, 4-chloro-5-methylisoxazol-3-yl group, 4,5-dibromoisoxazol-3-yl group, 4 -bromo-5-methylisoxazol-3-yl group, 4-bromo-5-ethylisoxazol-3-yl group, 4-bromo-5-isopropylisoxazol-3-yl group, 4-bromo -5-(difluoromethyl)isoxazol-3-yl group, 4-bromo-5-formylisoxazol-3-yl group, 4-bromo-5-(trimethylsilyl)isoxazol-3-yl group, 4,5- Diiodoisoxazol-3-yl group, 4-iodo-5-methylisoxazol-3-yl group, 4,5-dimethylisoxazol-3-yl group, 4-(hydroxymethyl)-5- methylisoxazol-3-yl group, 4-(difluoromethyl)-5-methylisoxazol-3-yl group, 4-(bromomethyl)-5-methylisoxazol-3-yl group, 4-( trifluoroacetoxymethyl)-5-methylisoxazol-3-yl group, 4-(1-hydroxyethyl)-5-methylisoxazol-3-yl group, 5-methyl-4-vinylisoxazole- 3-yl group, 4-ethynyl-5-methylisoxazol-3-yl group, 4-formyl-5-methylisoxazol-3-yl group, 4-acetyl-5-methylisoxazol-3-yl group The compound or a salt thereof according to any one of [1] to [9], which is an yl group or a 4-((methoxyimino)methyl)-5-methylisoxazol-3-yl group.
[16]
Substituent F is at least one selected from the group consisting of a halogen atom, an alkyl group optionally substituted with substituent C, and a C1-C6 alkoxy group optionally substituted with substituent C. , [1] to [3], [5] to [9], or a salt thereof.
[17]
any one of [1] to [3] and [5] to [9], wherein the substituent F is at least one selected from the group consisting of a bromine atom, a methyl group, an ethyl group, and an ethoxy group; The compound or its salt as described in .
[18]
An isoxazoline ring optionally substituted with 0 to 4 substituents F together with the oxime structure (C═N—O) to which R4 and R5 are attached each independently) are formed by 4-bromo-5,5-dimethyl-4,5-dihydroisoxazol-3-yl group, 5-ethyl-4,5-dihydroisoxazole- 3-yl group, 5,5-dimethyl-4,5-dihydroisoxazol-3-yl group, or 5-ethoxy-4,5-dihydroisoxazol-3-yl group [1]- The compound or salt thereof according to any one of [3], [5] to [9].
[19]
A benzisoxazole ring optionally substituted with 0 to 4 substituents D (provided that the substituents D in any one of [1] to [3] and [5] to [9], which is a benzo[d]isoxazol-3-yl group The described compound or a salt thereof.
[20]
An agricultural and horticultural pest control agent containing the compound according to any one of [1] to [19] or a salt thereof as an active ingredient.
[21]
An agricultural and horticultural fungicide containing the compound according to any one of [1] to [19] or a salt thereof as an active ingredient.
[22]
A method for controlling plant diseases, which comprises applying the agricultural and horticultural pest control agent according to [20] to plants, plant seeds, or soil for cultivating plants.
[23]
A method for controlling plant diseases, which comprises applying the agricultural and horticultural fungicide of [21] to plants, plant seeds, or soil for cultivating plants.

INDUSTRIAL APPLICABILITY According to the present invention, it is possible to provide novel compounds that are effective as agricultural and horticultural fungicides.

BEST MODE FOR CARRYING OUT THE INVENTION The best mode for carrying out the present invention will be described in detail below.

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

The abbreviations used in this specification are described below.
DMF: N,N-dimethylformamide, THF: tetrahydrofuran, Me: methyl group, Et: ethyl group, Pr: propyl group, Bu: butyl group, Pent: pentyl group, Hex: hexyl group, Ac: acetyl group, Ph: Phenyl group, Py: pyridyl group, c: cyclo, i: iso, sec: secondary, t: tertiary, =: double bond, ≡: triple bond. For Pr, Bu, Pent, and Hex in the columns of the table, no prefix means normal.

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

The term "optionally substituted" means substituted or unsubstituted. In using this term, if the number of substituents is not specified, it means that the number of substituents is one. On the other hand, for example, when the number of substituents is specified as "optionally substituted with 0 to 6", it is understood that all integers between 0 and 6 are also individually disclosed. be done. That is, it means that there are no, 1, 2, 3, 4, 5, or 6 substituents. Similarly, in "optionally 0 to 5 substituted", the number of substituents is none, 1, 2, 3, 4, or 5. In "optionally 0 to 4 substituted" , the number of substituents is none, 1, 2, 3, or 4, and ``optionally substituted with 0 to 3'' means ``no, 1, 2, or 3 substituents,'' and ``optionally "may be substituted with 0 to 2" means having no, 1, or 2 substituents, respectively.

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

A halogen atom includes a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, and the like.
The C1-C6 haloalkyl group represents a C1-C6 alkyl group in which the hydrogen in the above-mentioned C1-C6 alkyl group is optionally substituted with one or more halogen atoms. When substituted with two or more halogen atoms, those halogen atoms may be the same or different, and the number of substitutions is not particularly limited as long as they can exist as substituents. Specific examples of C1 to C6 haloalkyl groups include monofluoromethyl group, difluoromethyl group, trifluoromethyl group, monochloromethyl group, monobromomethyl group, monoiodomethyl group, chlorodifluoromethyl group, bromodifluoromethyl group, 1 -fluoroethyl group, 2-fluoroethyl group, 1,1-difluoroethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, 1,1,2,2-tetrafluoroethyl group , pentafluoroethyl group, 2,2,2-trichloroethyl group, 3,3-difluoropropyl group, 3,3,3-trifluoropropyl group, heptafluoropropyl group, heptafluoroisopropyl group, 2,2,2 -trifluoro-1-(trifluoromethyl)ethyl group, nonafluorobutyl group, nonafluoro-sec-butyl group, 3,3,4,4,5,5,5-heptafluoropentyl group, undecafluoropentyl group , tridecafluorohexyl group, and the like.

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

The C2-C6 alkenyl group means a linear or branched unsaturated hydrocarbon group having one or more double bonds. In addition, when there is a geometric isomer, it is either E-isomer or Z-isomer only, or a mixture of E-isomer and Z-isomer in any ratio, and if it is within the specified carbon number range, it is not particularly limited. never Specific examples of C2 to C6 alkenyl groups include vinyl group, 1-propenyl group, allyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 2-methyl-1-propenyl group, and 1-pentenyl group. , 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 2-methyl-1-butenyl group, 3-methyl-2-butenyl group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4 -hexenyl group, 5-hexenyl group, 4-methyl-3-pentenyl group, 3-methyl-2-pentenyl group and the like.

The C2-C6 haloalkenyl group represents a C2-C6 alkenyl group in which hydrogen atoms in the above-mentioned C2-C6 alkenyl groups are optionally substituted with one or more halogen atoms. When substituted with two or more halogen atoms, those halogen atoms may be the same or different, and the number of substitutions is not particularly limited as long as they can exist as substituents. Specific examples of C2 to C6 haloalkenyl groups include 2-fluorovinyl group, 2,2-difluorovinyl group, 2,2-dichlorovinyl group, 3-fluoroallyl group, 3,3-difluoroallyl group, 3, 3-dichloroallyl group, 4,4-difluoro-3-butenyl group, 5,5-difluoro-4-pentenyl group, 6,6-difluoro-5-hexenyl group and the like.

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

The C2-C6 haloalkynyl group represents a C2-C6 alkynyl group in which the hydrogen atoms in the above C2-C6 alkynyl group are optionally substituted with one or more halogen atoms. When substituted with two or more halogen atoms, those halogen atoms may be the same or different, and the number of substitutions is not particularly limited as long as they can exist as substituents. Specific examples of C2-C6 haloalkynyl groups include 2-fluoroethynyl, 2-chloroethynyl, 2-bromoethynyl, 2-iodoethynyl, 3,3-difluoro-1-propynyl, 3-chloro -3,3-difluoro-1-propynyl group, 3-bromo-3,3-difluoro-1-propynyl group, 3,3,3-trifluoro-1-propynyl group, 4,4-difluoro-1-butynyl group, 4,4-difluoro-2-butynyl group, 4-chloro-4,4-difluoro-1-butynyl group, 4-chloro-4,4-difluoro-2-butynyl group, 4-bromo-4,4 -difluoro-1-butynyl group, 4-bromo-4,4-difluoro-2-butynyl group, 4,4,4-trifluoro-1-butynyl group, 4,4,4-trifluoro-2-butynyl group , 5,5-difluoro-3-pentynyl group, 5-chloro-5,5-difluoro-3-pentynyl group, 5-bromo-5,5-difluoro-3-pentynyl group, 5,5,5-trifluoro -3-pentynyl group, 6,6-difluoro-4-hexynyl group, 6-chloro-6,6-difluoro-4-hexynyl group, 6-bromo-6,6-difluoro-4-hexynyl group, 6,6 , 6-trifluoro-4-hexynyl group and the like.

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

The C1-C6 haloalkoxy group represents a C1-C6 alkoxy group in which hydrogen atoms in the above C1-C6 alkoxy groups are optionally substituted with one or more halogen atoms. When substituted with two or more halogen atoms, those halogen atoms may be the same or different, and the number of substitutions is not particularly limited as long as they can exist as substituents. Specific examples of C1 to C6 haloalkoxy groups include difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2 -trifluoroethoxy group, 1,1,2,2-tetrafluoroethoxy group, pentafluoroethoxy group, 2,2,2-trichloroethoxy group, 3,3-difluoropropyloxy group, 3,3,3-tri fluoropropyloxy group, heptafluoropropyloxy group, heptafluoroisopropyloxy group, 2,2,2-trifluoro-1-(trifluoromethyl)-ethoxy group, nonafluorobutoxy group, nonafluoro-sec-butoxy group, 3 , 3,4,4,5,5,5-heptafluoropentyloxy group, undecafluoropentyloxy group, tridecafluorohexyloxy group and the like.

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

The C2-C6 alkenyloxy group represents a C2-C6 alkenyl group bonded via an oxygen atom. In addition, when there is a geometric isomer, it is either the E isomer or the Z isomer alone, or a mixture of the E isomer and the Z isomer in an arbitrary ratio, and if it is within the specified carbon number range, it is not particularly limited. never Specific examples of C2 to C6 alkenyloxy groups include vinyloxy, 1-propenyloxy, allyloxy, 1-butenyloxy, 2-butenyloxy, 3-butenyloxy, 2-methyl-1-propenyloxy, 1 -Pentenyloxy group, 2-pentenyloxy group, 3-pentenyloxy group, 4-pentenyloxy group, 2-methyl-1-butenyloxy group, 3-methyl-2-butenyloxy group, 1-hexenyloxy group, 2-hexenyl oxy group, 3-hexenyloxy group, 4-hexenyloxy group, 5-hexenyloxy group, 4-methyl-3-pentenyloxy group, 3-methyl-2-pentenyloxy group and the like.

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

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

The C3-C6 haloalkynyloxy group represents a C3-C6 alkynyloxy group in which hydrogen atoms in the above-mentioned C3-C6 alkynyloxy group are optionally substituted with one or more halogen atoms. When substituted with two or more halogen atoms, those halogen atoms may be the same or different, and the number of substitutions is not particularly limited as long as they can exist as substituents. Specific examples of C3-C6 haloalkynyloxy groups include 1,1-difluoro-2-propynyloxy group, 4,4-difluoro-2-butynyloxy group and 4-chloro-4,4-difluoro-2-butynyloxy group. , 4-bromo-4,4-difluoro-2-butynyloxy group, 4,4,4-trifluoro-2-butynyloxy group, 5,5-difluoro-3-pentynyloxy group, 5-chloro-5,5 -difluoro-3-pentynyloxy group, 5-bromo-5,5-difluoro-3-pentynyloxy group, 5,5,5-trifluoro-3-pentynyloxy group, 6,6-difluoro-4 -hexynyloxy group, 6-chloro-6,6-difluoro-4-hexynyloxy group, 6-bromo-6,6-difluoro-4-hexynyloxy group, 6,6,6-trifluoro-4-hexynyloxy group and the like. be done.

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

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

以下、式（１）について説明する。The pyridone compound of the present invention includes compounds represented by the following formula (1) and salts thereof. (hereinafter also referred to as the compound of the present invention).

Formula (1) will be described below.

R1 in formula (1) is a hydroxyl group, a cyano group, a C1 to C6 alkyl group optionally substituted with a substituent A, a C1 to C6 haloalkyl group optionally substituted with a substituent A, a C3 to 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-C6 alkoxy group optionally substituted with substituent A, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group optionally substituted with substituent A, substituted 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— (wherein Ra and Rb are each independently a hydrogen atom, a C1 to C6 alkyl group optionally substituted with a substituent B, a C1 to C6 haloalkyl group, or a C3 represents a ~C8 cycloalkyl group, or Ra and Rb together with the attached nitrogen atom form an aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl, homopiperidinyl, or azocanyl group ).

Among them, R1 is a C1-C6 alkyl group optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C2-C6 alkenyl group optionally substituted with a substituent A, a C2-C6 halo An alkenyl group, a C2-C6 alkynyl group optionally substituted with a substituent A, or a C2-C6 haloalkynyl group are preferred,
In particular, R1 is preferably a C1-C6 alkyl group optionally substituted with a substituent A or a C1-C6 haloalkyl group.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

“RaRbN—” for R1 in formula (1) (wherein Ra and Rb are each independently a hydrogen atom, a C1 to C6 alkyl group optionally substituted with a substituent B, a C1 to C6 represents a haloalkyl group or a C3-C8 cycloalkyl group, or Ra and Rb, together with the nitrogen atom to which they are attached, represent an aziridinyl group, azetidinyl group, pyrrolidinyl group, piperidinyl group, homopiperidinyl group, or azocanyl group; The definition of each term of "former" is the same as the definition given above. Regarding the "C1-C6 alkyl group optionally substituted with a substituent B", when the substituent B is present, the hydrogen atom in the C1-C6 alkyl group is optionally substituted with the substituent B. . "RaRbN-" is preferably 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, more preferably amino group, dimethylamino group , the ethylmethylamino group, and the diethylamino group.

R2 in formula (1) is a hydrogen atom, a cyano group, a nitro group, a halogen atom, a C1 to C6 alkyl group optionally substituted with a substituent A, a C1 to C6 haloalkyl group, or a substituent A as appropriate. optionally substituted C3-C8 cycloalkyl group, optionally substituted C2-C6 alkenyl group, C2-C6 haloalkenyl group optionally substituted with substituent A, C2- optionally substituted with substituent A C6 alkynyl group, C2-C6 haloalkynyl group, C1-C6 alkoxy group optionally substituted with substituent A, C1-C6 haloalkoxy group optionally substituted with substituent A C3- C8 cycloalkoxy group, C2-C6 alkenyloxy group optionally substituted with substituent A, C2-C6 haloalkenyloxy group, C3-C6 alkynyloxy group optionally substituted with substituent A , a C3-C6 haloalkynyloxy group, Rc-L- (wherein Rc represents a C1-C6 alkyl group or a C1-C6 haloalkyl group, and L represents S, SO, or SO ₂ ). ), RaRbN- (wherein Ra and Rb are as defined above), or RdC (=O)- (wherein Rd is a hydrogen atom, optionally substituted with a substituent B C1- C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group, or RaRbN— (where Ra and Rb are as defined above).

Among them, R2 is a hydrogen atom, a halogen atom, a C1-C6 alkyl group optionally substituted with a substituent A, a C1-C6 haloalkyl group, or a C2-C6 alkenyl group optionally substituted with a substituent A. , a C2-C6 alkynyl group optionally substituted with a substituent A, a C1-C6 alkoxy group optionally substituted with a substituent A, a C1-C6 haloalkoxy group, Rc-L- (where , Rc and L are as defined above), or RdC(=O)- (wherein Rd is as defined above),
In particular, R2 is a halogen atom, a C1-C6 alkyl group optionally substituted with a substituent A, a C2-C6 alkynyl group optionally substituted with a substituent A, or optionally substituted with a substituent A A good C1-C6 alkoxy group is preferred.

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

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

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

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

The C2-C6 alkenyl group of the "C2-C6 alkenyl group optionally substituted with a substituent A" for R2 in formula (1) has the same meaning as defined above, preferably a vinyl group, 1- It is a propenyl group, allyl group, 1-butenyl group, 2-butenyl group or 3-butenyl group, more preferably vinyl group, 1-propenyl group or allyl group. A hydrogen atom in the C2-C6 alkenyl group is optionally replaced by the substituent A, if the substituent A is present.

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

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

The “C2-C6 haloalkynyl group” for R2 in formula (1) has the same meaning as defined above, preferably 3,3-difluoro-1-propynyl group, 3,3,3-trifluoro-1 -propynyl group, 4,4-difluoro-1-butynyl group, 4,4-difluoro-2-butynyl group, 4,4,4-trifluoro-1-butynyl group, or 4,4,4-trifluoro- It is a 2-butynyl group, more preferably a 3,3-difluoro-1-propynyl group or a 3,3,3-trifluoro-1-propynyl group.

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

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

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

The C2-C6 alkenyloxy group in the "C2-C6 alkenyloxy group optionally substituted with a substituent A" for R2 in formula (1) has the same meaning as defined above, preferably a vinyloxy group, 1-propenyloxy group, allyloxy group, 1-butenyloxy group, 2-butenyloxy group or 3-butenyloxy group, more preferably vinyloxy group, 1-propenyloxy group or allyloxy group. A hydrogen atom in the C2-C6 alkenyloxy group is optionally replaced by the substituent A, if the substituent A is present.

The “C2-C6 haloalkenyloxy group” for R2 in formula (1) has the same meaning as defined above, and includes a 2-fluorovinyloxy group, a 2,2-difluorovinyloxy group, and 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-difluorovinyloxy group is.

The C3-C6 alkynyloxy group in the "C3-C6 alkynyloxy group optionally substituted with a substituent A" for R2 in formula (1) has the same definition as above, preferably a propargyloxy group. , 2-butynyloxy, or 3-butynyloxy, more preferably propargyloxy. A hydrogen atom in the C3-C6 alkynyloxy group is optionally replaced by the substituent A, if the substituent A is present.

The “C3-C6 haloalkynyloxy group” for R2 in formula (1) has the same meaning as defined above, preferably 4,4-difluoro-2-butynyloxy group, 4-chloro-4,4-difluoro -2-butynyloxy group, 4-bromo-4,4-difluoro-2-butynyloxy group, or 4,4,4-trifluoro-2-butynyloxy group, more preferably 4,4-difluoro-2- butynyloxy group, or 4,4,4-trifluoro-2-butynyloxy group.

"Rc-L-" for R2 in formula (1) (wherein Rc represents a C1-C6 alkyl group or a C1 _- C6 haloalkyl group, and L represents S, SO, or SO2.) each term has the same meaning as defined above. "Rc-L-" is preferably a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, a trifluoromethanesulfinyl group, or a trifluoromethanesulfonyl group, more preferably a methylthio group or a methanesulfinyl group. , or a methanesulfonyl group.

Ra and Rb of "RaRbN-" in R2 of formula (1) are the same as defined above. "RaRbN-" is preferably amino group, methylamino group, ethylamino group, propylamino group, isopropylamino group, (methoxymethyl)amino group, (2-methoxyethyl)amino group, (cyanomethyl)amino group, (2-cyanoethyl)amino group, dimethylamino group, ethyl (methyl)amino group, methyl (propyl)amino group, isopropyl (methyl)amino group, diethylamino group, ethyl (propyl)amino group, ethyl (isopropyl)amino group, (Methoxymethyl)methylamino group, (2-methoxyethyl)methylamino group, (cyanomethyl)methylamino group, (2-cyanoethyl)methylamino group, 2,2-difluoroethylamino group, 2,2,2-tri fluoroethylamino group, cyclopropylamino group, (cyclopropyl)methylamino group, pyrrolidinyl group or piperidinyl group, more preferably amino group, dimethylamino group, ethyl(methyl)amino group or diethylamino group .

"RdC(=O)-" for R2 in formula (1) (here, Rd is a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3 ~C8 cycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group, or RaRbN- (wherein Ra and Rb are as defined above) ) have the same meanings as defined above. Regarding the "C1-C6 alkyl group optionally substituted with a substituent B", when the substituent B is present, the hydrogen atom in the C1-C6 alkyl group is optionally substituted with the substituent B. . "RdC(=O)-" is preferably formyl group, acetyl group, methoxyacetyl group, cyanoacetyl group, propionyl group, difluoroacetyl group, trifluoroacetyl group, cyclopropanecarbonyl group, methoxycarbonyl group, ethoxycarbonyl group, 2,2-difluoroethoxycarbonyl group, 2,2,2-trifluoroethoxycarbonyl group, 3,3,3-trifluoropropyloxycarbonyl group, cyclopropyloxycarbonyl group, aminocarbonyl group, methylaminocarbonyl group , ethylaminocarbonyl group, (methoxymethyl)aminocarbonyl group, (2-methoxyethyl)aminocarbonyl group, (cyanomethyl)aminocarbonyl group, (2-cyanoethyl)aminocarbonyl group, dimethylaminocarbonyl group, ethyl (methyl)amino carbonyl group, diethylaminocarbonyl group, (methoxymethyl)methylaminocarbonyl group, (2-methoxyethyl)methylaminocarbonyl group, (cyanomethyl)methylaminocarbonyl group, (2-cyanoethyl)methylaminocarbonyl group, 2,2-difluoro ethylaminocarbonyl group, 2,2,2-trifluoroethylaminocarbonyl group, cyclopropylaminocarbonyl group, cyclopropyl(methyl)aminocarbonyl group, pyrrolidinylcarbonyl group, or piperidinylcarbonyl group, more preferably is an acetyl group, methoxyacetyl group, cyanoacetyl group, difluoroacetyl group, trifluoroacetyl group, methoxycarbonyl group, ethoxycarbonyl group, aminocarbonyl group, dimethylaminocarbonyl group, ethyl(methyl)aminocarbonyl group, or diethylaminocarbonyl is the base.

X in Formula (1) represents an oxygen atom or a sulfur atom. Preferred X is an oxygen atom.
Y in formula (1) is a phenyl group optionally substituted with R3 from 0 to 5 (provided that each of R3 is disubstituted or more is independent), optionally substituted with R3 from 0 to 4 good pyridyl group (however, in the case of two or more substituted R3, each independently ), a pyrimidinyl group optionally substituted with 0 to 3 substituents at R3 (however, in the case of R3 having 2 or more substitutions, each is independent), a pyrazinyl group optionally substituted with 0 to 3 substituents at R3 ( However, in the case of 2 or more substituted R3, each is independent.), a triazinyl group optionally substituted with 0 to 2 substituents with R3 (provided that, in the case of disubstituted R3, each is independent.), R3 a tetrazinyl group optionally substituted with R3, a thienyl group optionally substituted with 0 to 3 R3 (provided that each of R3 is disubstituted or more is independent), optionally substituted with 0 to 2 R3 A thiazolyl group (provided that, in the case of disubstituted R3, each independently ), or a thiadiazolyl group optionally substituted with R3.

Among them, Y is a phenyl group optionally substituted with 0 to 5 substituents by R3 (however, in the case of two or more substituted R3, each is independent), or a pyridyl group optionally substituted by 0 to 4 substituents by R3. (However, in the case of two or more substituted R3, each is independent.) is preferred,
In particular, Y is preferably a phenyl group which may optionally be substituted with 0 to 5 groups of R3 (provided that each of R3 groups having two or more substitutions is independent).

式（ａ）中、ｎａは０～５の整数を表し、ｎａ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し、同一もしくは異なっていてよく、任意に選択することができる。"A phenyl group optionally substituted with 0 to 5 R3" in Y of formula (1) (provided that each of R3 is disubstituted or more is independent.) is represented by formula (a). It represents the partial structure shown below.

In formula (a), na represents an integer of 0 to 5, and when na is 2 or more, each of the two or more substituted R3 represents an independent substituent, may be the same or different, and can be arbitrarily selected. can.

式（ｂ－１）、式（ｂ－２）および式（ｂ－３）中、ｎｂは０～４の整数を表し、ｎｂ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し、同一もしくは異なっていてよく、任意に選択することができる。"A pyridyl group optionally substituted with 0 to 4 R3" in Y of formula (1) (provided that each R3 is two or more substituted, each independently) is represented by formula (b-1), formula (b-2) and the following partial structures represented by formula (b-3) are represented.

In formula (b-1), formula (b-2) and formula (b-3), nb represents an integer of 0 to 4, and when nb is 2 or more, two or more substituted R3 are each independent substituents and may be the same or different and can be arbitrarily selected.

式（ｃ－１）、式（ｃ－２）および式（ｃ－３）中、ｎｃは０～３の整数を表し、ｎｃ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し、同一もしくは異なっていてよく、任意に選択することができる。The “pyridazinyl group optionally substituted with 0 to 3 R3” in Y of formula (1) (provided that each R3 is disubstituted or more is independent) is represented by formula (c-1), formula (c-2) and the following partial structures represented by formula (c-3) are represented.

In formula (c-1), formula (c-2) and formula (c-3), nc represents an integer of 0 to 3, and when nc is 2 or more, two or more substituted R3 are each independent substituents and may be the same or different and can be arbitrarily selected.

式（ｄ－１）、式（ｄ－２）および式（ｄ－３）中、ｎｄは０～３の整数を表し、ｎｄ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し、同一もしくは異なっていてよく、任意に選択することができる。"A pyrimidinyl group optionally substituted with 0 to 3 R3" in Y of formula (1) (provided that each R3 is two or more substituted, each independently) is represented by formula (d-1), formula (d-2) and the following partial structures represented by formula (d-3) are represented.

In formula (d-1), formula (d-2) and formula (d-3), nd represents an integer of 0 to 3, and when nd is 2 or more, two or more substituted R3 are each independent substituents and may be the same or different and can be arbitrarily selected.

式（ｅ）中、ｎｅは０～３の整数を表し、ｎｅ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し、同一もしくは異なっていてよく、任意に選択することができる。The "pyrazinyl group optionally substituted with 0 to 3 R3 (provided that each R3 is two or more substituents are independent.)" in Y of formula (1) is represented by formula (e). It represents the partial structure shown below.

In formula (e), ne represents an integer of 0 to 3, and when ne is 2 or more, each of the two or more substituted R3 represents an independent substituent, which may be the same or different, and can be arbitrarily selected. can.

式（ｆ－１）、式（ｆ－２）、式（ｆ－３）、式（ｆ－４）および式（ｆ－５）中、ｎｆは０～２の整数を表し、ｎｆが２の場合、２置換のＲ３はそれぞれ独立した置換基を表し、同一もしくは異なっていてよく、任意に選択することができる。The “triazinyl group optionally substituted with 0 to 2 substituents with R3” for Y in formula (1) (provided that each of the disubstituted R3 is independent) is represented by formula (f-1), formula ( f-2), formula (f-3), formula (f-4) and the following partial structures represented by formula (f-5).

In formula (f-1), formula (f-2), formula (f-3), formula (f-4) and formula (f-5), nf represents an integer of 0 to 2, and nf is 2 In this case, each disubstituted R3 represents an independent substituent, may be the same or different, and can be arbitrarily selected.

式（ｇ－１）、式（ｇ－２）および式（ｇ－３）中、ｎｇは０～１の整数を表す。The "tetrazinyl group optionally substituted with R3" in Y of formula (1) is the moiety shown below represented by formula (g-1), formula (g-2) and formula (g-3) Represent structure.

In formulas (g-1), (g-2) and (g-3), ng represents an integer of 0-1.

式（ｈ－１）および式（ｈ－２）中、ｎｈは０～３の整数を表し、ｎｈが２以上の場合、２以上のＲ３はそれぞれ独立した置換基を表し、同一もしくは異なっていてよく、任意に選択することができる。"A thienyl group optionally substituted with 0 to 3 R3" in Y of formula (1) (provided that each R3 is two or more substituted, each independently) is represented by formula (h-1) and formula It represents the partial structure shown below represented by (h-2).

In formula (h-1) and formula (h-2), nh represents an integer of 0 to 3, and when nh is 2 or more, 2 or more R3 each represent an independent substituent, the same or different Well, you can choose arbitrarily.

式（ｉ－１）、式（ｉ－２）および式（ｉ―３）中、ｎｉは０～２の整数を表し、ｎｉが２の場合、２置換のＲ３はそれぞれ独立した置換基を表し、同一もしくは異なっていてよく、任意に選択することができる。"A thiazolyl group optionally substituted with 0 to 2 substituents with R3" for Y in formula (1) (provided that, in the case of disubstituted R3, each is independent.) is represented by formula (i-1), formula ( i-2) and the following partial structures represented by formula (i-3).

In formula (i-1), formula (i-2) and formula (i-3), ni represents an integer of 0 to 2, and when ni is 2, each of the disubstituted R3 represents an independent substituent. , may be the same or different and can be arbitrarily selected.

式（ｊ－１）、式（ｊ－２）および式（ｊ―３）中、ｎｊは０～２の整数を表し、ｎｊが２の場合、２置換のＲ３はそれぞれ独立した置換基を表し、同一もしくは異なっていてよく、任意に選択することができる。The “isothiazolyl group optionally substituted with 0 to 2 substituents with R3” for Y in formula (1) (provided that each of the disubstituted R3 is independent) is represented by formula (j-1), formula ( j-2) and the following partial structures represented by formula (j-3).

In formula (j-1), formula (j-2) and formula (j-3), nj represents an integer of 0 to 2, and when nj is 2, each disubstituted R3 represents an independent substituent. , may be the same or different and can be arbitrarily selected.

式（ｋ－１）、式（ｋ－２）、式（ｋ－３）、式（ｋ－４）、式（ｋ－５）および式（ｋ－６）中、ｎｋは０～１の整数を表す。The "thiadiazolyl group optionally substituted with R3" in Y of formula (1) is represented by formula (k-1), formula (k-2), formula (k-3), formula (k-4), formula (k-5) and the following partial structures represented by formula (k-6) are represented.

In formula (k-1), formula (k-2), formula (k-3), formula (k-4), formula (k-5) and formula (k-6), nk is an integer of 0 to 1 represents

R3 in formula (1) is a hydroxyl group, a cyano group, a nitro group, a halogen atom, a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group, optionally substituted with a substituent C a C3-C8 cycloalkyl group optionally substituted with a substituent C, a C2-C6 alkenyl group optionally substituted with a substituent C, a C2-C6 haloalkenyl group optionally substituted with a substituent C, a C2-C6 optionally substituted with a substituent C C2-C6 haloalkynyl group, C1-C6 alkoxy group optionally substituted with substituent C, C1-C6 haloalkoxy group, C3-C8 optionally substituted with substituent C a cycloalkoxy group, a C2 to C6 alkenyloxy group optionally substituted with a substituent C, a C2 to C6 haloalkenyloxy group, a C3 to C6 alkynyloxy group optionally substituted with a substituent C, C3-C6 haloalkynyloxy groups, RdC(=O)- (wherein Rd is as defined above), RdC(=O)O- (wherein Rd is as defined above). ), a 3- to 6-membered ring group containing 1 to 2 oxygen atoms, Rc-L- (wherein Rc and L are as defined above), RaRbN- (wherein Ra and Rb are , as defined above), or ReC(=O)N(Rf)- (wherein Re and Rf are each independently a hydrogen atom, optionally substituted with a substituent B C1 to C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group, or RaRbN— (where Ra and Rb are as defined above.).

Among them, R3 is a hydroxyl group, a cyano group, a halogen atom, a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 alkoxy group optionally substituted with a substituent C, a C1-C6 haloalkoxy 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 or RdC(=O)O- (wherein Rd is as defined above) is preferred,
In particular, R3 is preferably a cyano group, a halogen atom, or a C1-C6 alkoxy group optionally substituted with a substituent C.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Rd of "RdC(=O)-" in R3 of formula (1) has the same meaning as defined above. "RdC(=O)-" is preferably formyl group, acetyl group, methoxyacetyl group, cyanoacetyl group, propionyl group, difluoroacetyl group, trifluoroacetyl group, cyclopropanecarbonyl group, methoxycarbonyl group, ethoxycarbonyl group, 2,2-difluoroethoxycarbonyl group, 2,2,2-trifluoroethoxycarbonyl group, 3,3,3-trifluoropropyloxycarbonyl group, cyclopropyloxycarbonyl group, aminocarbonyl group, methylaminocarbonyl group , ethylaminocarbonyl group, (methoxymethyl)aminocarbonyl group, (2-methoxyethyl)aminocarbonyl group, (cyanomethyl)aminocarbonyl group, (2-cyanoethyl)aminocarbonyl group, dimethylaminocarbonyl group, ethyl (methyl)amino carbonyl group, diethylaminocarbonyl group, (methoxymethyl)methylaminocarbonyl group, (2-methoxyethyl)methylaminocarbonyl group, (cyanomethyl)methylaminocarbonyl group, (2-cyanoethyl)methylaminocarbonyl group, 2,2-difluoro ethylaminocarbonyl group, 2,2,2-trifluoroethylaminocarbonyl group, cyclopropylaminocarbonyl group, cyclopropyl(methyl)aminocarbonyl group, pyrrolidinylcarbonyl group, or piperidinylcarbonyl group, more preferably is an acetyl group, methoxyacetyl group, cyanoacetyl group, difluoroacetyl group, trifluoroacetyl group, methoxycarbonyl group, ethoxycarbonyl group, aminocarbonyl group, dimethylaminocarbonyl group, ethyl(methyl)aminocarbonyl group, or diethylaminocarbonyl is the base.

Rd of "RdC(=O)O-" in R3 of formula (1) has the same meaning as defined above. "RdC(=O)O-" is preferably formyloxy group, acetyloxy group, methoxyacetyloxy group, cyanoacetyloxy group, propionyloxy group, difluoroacetyloxy group, trifluoroacetyloxy group, cyclopropanecarbonyl 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, ethyl(methyl)aminocarbonyloxy group, diethylaminocarbonyloxy group, (methoxymethyl)methylaminocarbonyloxy group, (2-methoxyethyl)methylamino carbonyloxy group, (cyanomethyl)methylaminocarbonyloxy group, (2-cyanoethyl)methylaminocarbonyloxy group, 2,2-difluoroethylaminocarbonyloxy group, 2,2,2-trifluoroethylaminocarbonyloxy group, cyclo propylaminocarbonyloxy group, cyclopropyl(methyl)aminocarbonyloxy group, pyrrolidinylcarbonyloxy group, or piperidinylcarbonyloxy group, more preferably acetyloxy group, methoxyacetyloxy group, cyanoacetyloxy group , a difluoroacetyloxy group, a trifluoroacetyloxy group, a methoxycarbonyloxy group, an ethoxycarbonyloxy group, an aminocarbonyloxy group, a dimethylaminocarbonyloxy group, an ethyl(methyl)aminocarbonyloxy group, or a diethylaminocarbonyloxy group.

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

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

Ra and Rb of "RaRbN-" in R3 of formula (1) are the same as defined above. "RaRbN-" is preferably amino group, methylamino group, ethylamino group, propylamino group, isopropylamino group, (methoxymethyl)amino group, (2-methoxyethyl)amino group, (cyanomethyl)amino group, (2-cyanoethyl)amino group, dimethylamino group, ethyl(methyl)amino group, methyl(propyl)amino group, isopropyl(methyl)amino group, (methoxymethyl)methylamino group, (2-methoxyethyl)methylamino group , (cyanomethyl)methylamino group, (2-cyanoethyl)methylamino group, diethylamino group, ethyl (propyl)amino group, ethyl (isopropyl)amino group, ethyl (methoxymethyl)amino group, ethyl (2-methoxyethyl)amino group, (cyanomethyl)ethylamino group, (2-cyanoethyl)ethylamino 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, ethyl(methyl)amino group, isopropyl(methyl)amino group, diethylamino group or ethyl(isopropyl)amino group.

"ReC(=O)N(Rf)-" for R3 in formula (1) (where Re and Rf are each independently a hydrogen atom, C1 to C6 optionally substituted with a substituent B alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group, or RaRbN- (where Ra and Rb have the same meanings as defined above. Regarding the "C1-C6 alkyl group optionally substituted with a substituent B", when the substituent B is present, the hydrogen atom in the C1-C6 alkyl group is optionally substituted with the substituent B. . "ReC(=O)N(Rf)-" is preferably a formylamino group, an acetylamino group, a methoxyacetylamino group, a cyanoacetylamino group, a propionylamino group, a difluoroacetylamino group, a trifluoroacetylamino group, cyclopropanecarbonylamino group, methoxycarbonylamino group, ethoxycarbonylamino group, 2,2-difluoroethoxycarbonylamino group, 2,2,2-trifluoroethoxycarbonylamino group, 3,3,3-trifluoropropyloxycarbonyl amino group, cyclopropyloxycarbonylamino group, aminocarbonylamino group, methylaminocarbonylamino group, ethylaminocarbonylamino group, (methoxymethyl)aminocarbonylamino group, (2-methoxyethyl)aminocarbonylamino group, (cyanomethyl) aminocarbonylamino group, (2-cyanoethyl)aminocarbonylamino group, dimethylaminocarbonylamino group, ethyl(methyl)aminocarbonylamino group, diethylaminocarbonylamino group, (methoxymethyl)methylaminocarbonylamino group, (2-methoxyethyl ) methylaminocarbonylamino group, (cyanomethyl)methylaminocarbonylamino group, (2-cyanoethyl)methylaminocarbonylamino group, 2,2-difluoroethylaminocarbonylamino group, 2,2,2-trifluoroethylaminocarbonylamino group, cyclopropylaminocarbonylamino group, cyclopropyl(methyl)aminocarbonylamino group, pyrrolidinylcarbonylamino group, piperidinylcarbonylamino group, formyl(methyl)amino group, acetyl(methyl)amino group, methoxyacetyl ( methyl)amino group, cyanoacetyl(methyl)amino group, propionyl(methyl)amino group, difluoroacetyl(methyl)amino group, trifluoroacetyl(methyl)amino group, cyclopropanecarbonyl(methyl)amino group, methoxycarbonyl(methyl)amino group ) amino group, ethoxycarbonyl (methyl) amino group, 2,2-difluoroethoxycarbonyl (methyl) amino group, 2,2,2-trifluoroethoxycarbonyl (methyl) amino group, 3,3,3-trifluoropropyl oxycarbonyl(methyl)amino group, cyclopropyloxycarbonyl(methyl)amino group, aminocarbonyl(methyl)amino group, methylaminocarbonyl(methyl)amino group Chill)amino group, ethylaminocarbonyl(methyl)amino group, (methoxymethyl)aminocarbonyl(methyl)amino group, (2-methoxyethyl)aminocarbonyl(methyl)amino group, (cyanomethyl)aminocarbonyl(methyl)amino group , (2-cyanoethyl)aminocarbonyl(methyl)amino group, dimethylaminocarbonyl(methyl)amino group, ethyl(methyl)aminocarbonyl(methyl)amino group, diethylaminocarbonyl(methyl)amino group, (methoxymethyl)methylaminocarbonyl (methyl)amino group, (2-methoxyethyl)methylaminocarbonyl(methyl)amino group, (cyanomethyl)methylaminocarbonyl(methyl)amino group, (2-cyanoethyl)methylaminocarbonyl(methyl)amino group, 2,2 -difluoroethylaminocarbonyl(methyl)amino group, 2,2,2-trifluoroethylaminocarbonyl(methyl)amino group, cyclopropylaminocarbonyl(methyl)amino group, cyclopropyl(methyl)aminocarbonyl(methyl)amino group , pyrrolidinylcarbonyl(methyl)amino group, piperidinylcarbonyl(methyl)amino group, formyl(ethyl)amino group, acetyl(ethyl)amino group, methoxyacetyl(ethyl)amino group, cyanoacetyl(ethyl)amino group , propionyl (ethyl) amino group, difluoroacetyl (ethyl) amino group, trifluoroacetyl (ethyl) amino group, cyclopropanecarbonyl (ethyl) amino group, methoxycarbonyl (ethyl) amino group, ethoxycarbonyl (ethyl) amino group, 2,2-difluoroethoxycarbonyl(ethyl)amino group, 2,2,2-trifluoroethoxycarbonyl(ethyl)amino group, 3,3,3-trifluoropropyloxycarbonyl(ethyl)amino group, cyclopropyloxycarbonyl (ethyl)amino group, aminocarbonyl(ethyl)amino group, methylaminocarbonyl(ethyl)amino group, ethylaminocarbonyl(ethyl)amino group, (methoxymethyl)aminocarbonyl(ethyl)amino group, (2-methoxyethyl) aminocarbonyl(ethyl)amino group, (cyanomethyl)aminocarbonyl(ethyl)amino group, (2-cyanoethyl)aminocarbonyl(ethyl)amino group, dimethylaminocarbonyl(ethyl)amino group, ethyl(methyl)aminocarbonyl(ethyl) amino group, diethylaminocarbonyl(ethyl)amino group, (methoxymethyl)methylaminocarbonyl(ethyl)amino group, (2-methoxyethyl)methylaminocarbonyl(ethyl)amino group, (cyanomethyl)methylaminocarbonyl(ethyl)amino group , (2-cyanoethyl)methylaminocarbonyl (ethyl)amino group, 2,2-difluoroethylaminocarbonyl (ethyl)amino group, 2,2,2-trifluoroethylaminocarbonyl (ethyl)amino group, cyclopropylaminocarbonyl (ethyl)amino group, cyclopropyl(methyl)aminocarbonyl(ethyl)amino group, pyrrolidinylcarbonyl(ethyl)amino group, piperidinylcarbonyl(ethyl)amino group, formyl(methoxy)amino group, acetyl(methoxy) amino group, methoxyacetyl(methoxy)amino group, cyanoacetyl(methoxy)amino group, propionyl(methoxy)amino group, difluoroacetyl(methoxy)amino group, trifluoroacetyl(methoxy)amino group, cyclopropanecarbonyl(methoxy)amino group group, methoxycarbonyl (methoxy) amino group, ethoxycarbonyl (methoxy) amino group, 2,2-difluoroethoxycarbonyl (methoxy) amino group, 2,2,2-trifluoroethoxycarbonyl (methoxy) amino group, 3,3 , 3-trifluoropropyloxycarbonyl (methoxy) amino group, cyclopropyloxycarbonyl (methoxy) amino group, aminocarbonyl (methoxy) amino group, methylaminocarbonyl (methoxy) amino group, ethylaminocarbonyl (methoxy) amino group, (methoxymethyl)aminocarbonyl(methoxy)amino group, (2-methoxyethyl)aminocarbonyl(methoxy)amino group, (cyanomethyl)aminocarbonyl(methoxy)amino group, (2-cyanoethyl)aminocarbonyl(methoxy)amino group, dimethylaminocarbonyl(methoxy)amino group, ethyl(methyl)aminocarbonyl(methoxy)amino group, diethylaminocarbonyl(methoxy)amino group, (methoxymethyl)methylaminocarbonyl(methoxy)amino group, (2-methoxyethyl)methylamino carbonyl (methoxy) amino group, (cyanomethyl) methylaminocarbonyl (methoxy) amino group, (2-cyanoethyl) methylaminocarbonyl (methoxy) amino group, 2,2-di fluoroethylaminocarbonyl(methoxy)amino group, 2,2,2-trifluoroethylaminocarbonyl(methoxy)amino group, cyclopropylaminocarbonyl(methoxy)amino group, cyclopropyl(methyl)aminocarbonyl(methoxy)amino group, pyrrolidinylcarbonyl(methoxy)amino group, piperidinylcarbonyl(methoxy)amino group, formyl(ethoxy)amino group, acetyl(ethoxy)amino group, methoxyacetyl(ethoxy)amino group, cyanoacetyl(ethoxy)amino group, propionyl (ethoxy) amino group, difluoroacetyl (ethoxy) amino group, trifluoroacetyl (ethoxy) amino group, cyclopropanecarbonyl (ethoxy) amino group, methoxycarbonyl (ethoxy) amino group, ethoxycarbonyl (ethoxy) amino group, 2 , 2-difluoroethoxycarbonyl (ethoxy) amino group, 2,2,2-trifluoroethoxycarbonyl (ethoxy) amino group, 3,3,3-trifluoropropyloxycarbonyl (ethoxy) amino group, cyclopropyloxycarbonyl ( ethoxy)amino group, aminocarbonyl(ethoxy)amino group, methylaminocarbonyl(ethoxy)amino group, ethylaminocarbonyl(ethoxy)amino group, (methoxymethyl)aminocarbonyl(ethoxy)amino group, (2-methoxyethyl)amino carbonyl (ethoxy) amino group, (cyanomethyl) aminocarbonyl (ethoxy) amino group, (2-cyanoethyl) aminocarbonyl (ethoxy) amino group, dimethylaminocarbonyl (ethoxy) amino group, ethyl (methyl) aminocarbonyl (ethoxy) amino group group, diethylaminocarbonyl(ethoxy)amino group, (methoxymethyl)methylaminocarbonyl(ethoxy)amino group, (2-methoxyethyl)methylaminocarbonyl(ethoxy)amino group, (cyanomethyl)methylaminocarbonyl(ethoxy)amino group, (2-cyanoethyl) methylaminocarbonyl (ethoxy) amino group, 2,2-difluoroethylaminocarbonyl (ethoxy) amino group, 2,2,2-trifluoroethylaminocarbonyl (ethoxy) amino group, cyclopropylaminocarbonyl ( ethoxy)amino group, cyclopropyl(methyl)aminocarbonyl(ethoxy)amino group, pyrrolidinylcarbonyl(ethoxy)amino group, or piperidinyl carbonyl(ethoxy)amino group, more preferably acetylamino group, acetyl(methyl)amino group, acetyl(ethyl)amino group, acetyl(methoxy)amino group, acetyl(ethoxy)amino group, methoxycarbonylamino group , ethoxycarbonylamino group, methoxycarbonyl(methyl)amino group, ethoxycarbonyl(methyl)amino group, methoxycarbonyl(ethyl)amino group, ethoxycarbonyl(ethyl)amino group, methoxycarbonyl(methoxy)amino group, ethoxycarbonyl(methoxy ) amino group, methoxycarbonyl(ethoxy)amino group, or ethoxycarbonyl(ethoxy)amino group.

R4 in formula (1) is a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group, a C3-C8 optionally substituted with a substituent C a 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, a C2-C6 a haloalkynyl group, a phenyl group optionally substituted with 0 to 5 substituents D (however, in the case of disubstituted or more substituents D, each is independent), optionally substituted with 0 to 5 substituents D a C1 to C6 alkyl group having a phenyl group which may be optionally substituted (however, in the case of disubstituted or more substituents D, each is independent); represents a C1 to C6 haloalkyl group having (provided that, in the case of disubstituted or more substituents D, each is independent), or RaRbN- (wherein Ra and Rb are as defined above).

Among them, R4 is a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with a substituent C, substituted C2-C6 alkenyl group optionally substituted by group C, C2-C6 haloalkenyl group, C2-C6 alkynyl group optionally substituted by substituent C, C2-C6 haloalkynyl group, substituted A phenyl group optionally substituted with 0 to 5 groups D (however, in the case of disubstituted or more substituents D, each is independent), or RaRbN- (wherein Ra and Rb are as defined above). ) is preferred,
In particular, R4 is a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent C, a C3-C8 cycloalkyl group optionally substituted with a substituent C, a substituent D optionally from 0 to 5 An optionally substituted phenyl group (however, in the case of disubstituted or more substituents D, each is independent) or RaRbN- (wherein Ra and Rb are as defined above) are preferred.

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

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

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

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

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

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

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

The "phenyl group optionally substituted with 0 to 5 substituents D" in R4 of formula (1) (provided that, in the case of two or more substituents D, each is independent), the substituent D optionally substituted by a substituent D for a hydrogen atom in the phenyl group.

"C1-C6 alkyl group having a phenyl group optionally substituted with 0 to 5 substituents D" in R4 of formula (1) (however, in the case of two or more substituents D, each independently .), “a phenyl group optionally substituted with 0 to 5 substituents D” and “a C1 to C6 alkyl group” have the same meanings as defined above. The "C1-C6 alkyl group having a phenyl group" is preferably a phenylmethyl group, a 2-phenylethyl group, a 1-phenylethyl group, a 3-phenylpropyl group, a 2-phenylpropyl group and a 1-phenylpropyl group. , 4-phenylbutyl group or 5-phenylpentyl group, more preferably phenylmethyl group, 2-phenylethyl group, 1-phenylethyl group or 1-phenylpropyl group. A hydrogen atom in the phenyl group is optionally replaced by the substituent D, if the substituent D is present.

"C1-C6 haloalkyl group having a phenyl group optionally substituted with 0 to 5 substituents D" in R4 of formula (1) (however, in the case of two or more substituents D, each independently .), “a phenyl group optionally substituted with 0 to 5 substituents D” and “a C1 to C6 haloalkyl group” have the same meanings as defined above. The "C1-C6 haloalkyl group having a phenyl group" is preferably a 2,2,2-trifluoro-1-phenylethyl group or a 2,2-difluoro-1-phenylethyl group, more preferably , 2,2,2-trifluoro-1-phenylethyl group. A hydrogen atom in the phenyl group is optionally replaced by the substituent D, if the substituent D is present.

Ra and Rb of "RaRbN-" in R4 of formula (1) are the same as defined above. Ra and Rb are preferably a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, or a C1-C6 haloalkyl group, more preferably a hydrogen atom, or a substituent B It is an optionally substituted C1-C6 alkyl group. "RaRbN-" is preferably amino group, methylamino group, ethylamino group, propylamino group, isopropylamino group, (methoxymethyl)amino group, (2-methoxyethyl)amino group, (cyanomethyl)amino group, (2-cyanoethyl)amino group, dimethylamino group, ethyl(methyl)amino group, methyl(propyl)amino group, isopropyl(methyl)amino group, (methoxymethyl)methylamino group, (2-methoxyethyl)methylamino group , (cyanomethyl)methylamino group, (2-cyanoethyl)methylamino group, diethylamino group, ethyl (propyl)amino group, ethyl (isopropyl)amino group, ethyl (methoxymethyl)amino group, ethyl (2-methoxyethyl)amino group, (cyanomethyl)ethylamino group, (2-cyanoethyl)ethylamino 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, ethylamino group, propylamino group, dimethylamino group, ethyl(methyl)amino group or diethylamino group.

R5 in formula (1) is a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group, a C3-C8 optionally substituted with a substituent C a 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, a C2-C6 a haloalkynyl group, a phenyl group optionally substituted with 0 to 5 substituents D (however, in the case of disubstituted or more substituents D, each is independent), optionally substituted with 0 to 5 substituents D a C1 to C6 alkyl group having a phenyl group which may be optionally substituted (however, in the case of disubstituted or more substituents D, each is independent); a C1 to C6 haloalkyl group (provided that, in the case of disubstituted or more substituents D, each is independent), or RdC(=O)- (wherein Rd is as defined above.) show.

Among them, R5 is a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with a substituent C, a substituted a C2-C6 alkenyl group optionally substituted with a group C, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group optionally substituted with a substituent C, a C2-C6 haloalkynyl group, or RdC (=O) - (wherein Rd is as defined above) is preferred,
In particular, R5 is preferably a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent C, or RdC(=O)- (wherein Rd is as defined above).

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

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

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

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

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

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

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

The “phenyl group optionally substituted with 0 to 5 substituents D” in R5 of formula (1) (provided that, in the case of two or more substituents D, each is independent), the substituent D optionally substituted by a substituent D for a hydrogen atom in the phenyl group.

"A C1-C6 alkyl group having a phenyl group optionally substituted with 0 to 5 substituents D" for R5 in formula (1) (however, in the case of two or more substituents D, each independently .), “a phenyl group optionally substituted with 0 to 5 substituents D” and “a C1 to C6 alkyl group” have the same meanings as defined above. The "C1-C6 alkyl group having a phenyl group" is preferably a phenylmethyl group, a 2-phenylethyl group, a 1-phenylethyl group, a 3-phenylpropyl group, a 2-phenylpropyl group and a 1-phenylpropyl group. , 4-phenylbutyl group or 5-phenylpentyl group, more preferably phenylmethyl group, 2-phenylethyl group, 1-phenylethyl group or 1-phenylpropyl group. A hydrogen atom in the phenyl group is optionally replaced by the substituent D, if the substituent D is present.

"A C1-C6 haloalkyl group having a phenyl group optionally substituted with 0 to 5 substituents D" for R5 in formula (1) (however, in the case of two or more substituents D, each independently .), “a phenyl group optionally substituted with 0 to 5 substituents D” and “a C1 to C6 haloalkyl group” have the same meanings as defined above. The "C1-C6 haloalkyl group having a phenyl group" is preferably a 2,2,2-trifluoro-1-phenylethyl group or a 2,2-difluoro-1-phenylethyl group, more preferably , 2,2,2-trifluoro-1-phenylethyl group. A hydrogen atom in the phenyl group is optionally replaced by the substituent D, if the substituent D is present.

Rd of "RdC(=O)-" in R5 of formula (1) has the same definition as above. Rd is preferably a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group, more preferably a substituent B as appropriate It is an optionally substituted C1-C6 alkyl group. "RdC(=O)-" is preferably formyl group, acetyl group, methoxyacetyl group, cyanoacetyl group, propionyl group, difluoroacetyl group, trifluoroacetyl group, cyclopropanecarbonyl group, methoxycarbonyl group, ethoxycarbonyl group, 2,2-difluoroethoxycarbonyl group, 2,2,2-trifluoroethoxycarbonyl group, 3,3,3-trifluoropropyloxycarbonyl group, cyclopropyloxycarbonyl group, aminocarbonyl group, methylaminocarbonyl group , ethylaminocarbonyl group, (methoxymethyl)aminocarbonyl group, (2-methoxyethyl)aminocarbonyl group, (cyanomethyl)aminocarbonyl group, (2-cyanoethyl)aminocarbonyl group, dimethylaminocarbonyl group, ethyl (methyl)amino carbonyl group, diethylaminocarbonyl group, (methoxymethyl)methylaminocarbonyl group, (2-methoxyethyl)methylaminocarbonyl group, (cyanomethyl)methylaminocarbonyl group, (2-cyanoethyl)methylaminocarbonyl group, 2,2-difluoro ethylaminocarbonyl group, 2,2,2-trifluoroethylaminocarbonyl group, cyclopropylaminocarbonyl group, cyclopropyl(methyl)aminocarbonyl group, pyrrolidinylcarbonyl group, or piperidinylcarbonyl group, more preferably is an acetyl group, a methoxyacetyl group, a cyanoacetyl group, or a propionyl group.

R4 and R5 in formula (1), together with the oxime structure (C=N-O) to which they are bonded, isoxazole ring optionally substituted 0-2 by substituent E (provided that disubstituted In the case of substituents E, each is independent.), isoxazoline ring optionally substituted with 0 to 4 substituents F (provided that, in the case of two or more substituents F, each is independent.), A benzisoxazole ring optionally substituted with 0 to 4 substituents D (however, in the case of disubstituted or more substituents D, each is independent), or optionally substituted with 0 to 6 substituents F 5,6-dihydro-4H-1,2-oxazine ring (provided that, in the case of two or more substituents F, each is independent).

Among them, R4 and R5, together with the oxime structure (C=N-O) to which they are bound, are an isoxazole ring optionally substituted with 0 to 2 substituents E (however, in the case of a disubstituted substituent E, each independently.), an isoxazoline ring optionally substituted with 0 to 4 substituents F (provided that, in the case of two or more substituents F, each is independent.), or a substituent D as appropriate preferably form a benzisoxazole ring optionally substituted with 0 to 4 substituents (provided that, in the case of disubstituted or more substituents D, each is independent),
In particular, R4 and R5, together with the oxime structure (C=N-O) to which they are bound, are an isoxazole ring optionally substituted 0-2 with a substituent E (provided that in the case of a disubstituted substituent E, are each independent).

で表される。R4 and R5 in formula (1) together with the bonding oxime structure (C=N-O) form an isoxazole ring optionally substituted with 0 to 2 substituents E (provided that In the case of disubstituted substituents E, each is independent.) is represented by formula (2)

is represented by

R6 and R7 in formula (2) each independently represent a hydrogen atom or a substituent E, and R1, R2, X and Y are as defined above.

Specifically, R6 in formula (2) is a hydrogen atom, a hydroxyl group, a cyano group, a halogen atom, a C1 to C6 alkyl group optionally substituted with a substituent C, a C1 to C6 haloalkyl group, a substituent C3-C8 cycloalkyl group optionally substituted with C, C2-C6 alkenyl group optionally substituted with substituent C, C2-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 C3-C8 cycloalkoxy group, C2-C6 alkenyloxy group optionally substituted with substituent C, C2-C6 haloalkenyloxy group, C3-C6 alkynyl optionally substituted with substituent C oxy group, C3-C6 haloalkynyloxy group, C2-C6 alkoxyalkoxy group, RaRbN- (wherein Ra and Rb are as defined above), Rc-L- (wherein Rc and L is as defined above.), RdC(=O)-(wherein Rd is as defined above.), RdC(=O)O-(wherein Rd is as defined above ), RgON=C(Rh)- (where Rg and Rh each independently represent a hydrogen atom or a C1-C6 alkyl group), RiRjRkSi- (where Ri, Rj and Rk each independently represent a C1-C6 alkyl group), or a 3- to 6-membered ring group containing 1 to 2 oxygen atoms.

Among them, R6 is a hydrogen atom, a cyano group, a halogen atom, a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group optionally substituted with a substituent C, a C2-C6 optionally substituted with a substituent C alkenyl group, C2-C6 haloalkenyl group, C2-C6 alkynyl group optionally substituted with substituent C, C2-C6 haloalkynyl group, RdC(=O)- (wherein Rd is ), or RgON=C(Rh)-(where Rg and Rh are as defined above) are preferred,
In particular, R6 is a hydrogen atom, a halogen atom, a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group, a C2-C6 alkenyl group optionally substituted with a substituent C, A C2-C6 alkynyl group optionally substituted with a substituent C, RdC(=O)- (wherein Rd is as defined above), or RgON=C(Rh)- (where Rg and Rh are as defined above.) is preferred.

Preferred examples of each substituent of R6 are the same as those described for the substituent E.

Specifically, R7 in formula (2) is a hydrogen atom, a hydroxyl group, a cyano group, a halogen atom, a C1 to C6 alkyl group optionally substituted with a substituent C, a C1 to C6 haloalkyl group, a substituent C3-C8 cycloalkyl group optionally substituted with C, C2-C6 alkenyl group optionally substituted with substituent C, C2-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 C3-C8 cycloalkoxy group, C2-C6 alkenyloxy group optionally substituted with substituent C, C2-C6 haloalkenyloxy group, C3-C6 alkynyl optionally substituted with substituent C oxy group, C3-C6 haloalkynyloxy group, C2-C6 alkoxyalkoxy group, RaRbN- (wherein Ra and Rb are as defined above), Rc-L- (wherein Rc and L is as defined above.), RdC(=O)-(wherein Rd is as defined above.), RdC(=O)O-(wherein Rd is as defined above ), RgON=C(Rh)- (wherein Rg and Rh are as defined above), RiRjRkSi- (wherein Ri, Rj and Rk are each independently C1-C6 alkyl group), or a 3- to 6-membered ring group containing 1 to 2 oxygen atoms.

Among them, R7 is a hydrogen atom, a cyano group, a halogen atom, a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group optionally substituted with a substituent C, a C2-C6 optionally substituted with a substituent C alkenyl group, C2-C6 haloalkenyl group, C2-C6 alkynyl group optionally substituted with substituent C, C2-C6 haloalkynyl group, RaRbN- (wherein Ra and Rb are as defined above) ), RdC(=O)- (wherein Rd is as defined above), or RiRjRkSi- (wherein Ri, Rj and Rk are each independently C1-C6 alkyl represents a group.) is preferred,
In particular, R7 is a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group, RaRbN- (wherein Ra and Rb are as defined above), RdC(=O)- (wherein Rd is as defined above), or RiRjRkSi- (wherein Ri, Rj and Rk each independently represent a C1-C6 alkyl group.) is preferred.

Preferred examples of each substituent of R7 are the same as those described for the substituent E.

で表される。R4 and R5 in formula (1) together with the bonding oxime structure (C═N—O) form an isoxazoline ring optionally substituted with 0 to 4 substituents F (provided that In the case of two or more substituents F, each is independent.) is represented by formula (3)

is represented by

In formula (3), R8, R9, R10 and R11 each independently represent a hydrogen atom or a substituent F, and R1, R2, X and Y are as defined above.

R8 and R9 in formula (3) are each independently, specifically, a hydrogen atom, a hydroxyl group, a cyano group, a halogen atom, a C1-C6 alkyl group optionally substituted with a substituent C, C1-C6 haloalkyl group, C3-C8 cycloalkyl group optionally substituted with substituent C, C2-C6 alkenyl group optionally substituted with substituent C, C2-C6 haloalkenyl group, substituted C2-C6 alkynyl group optionally substituted with group C, C2-C6 haloalkynyl group, C1-C6 alkoxy group optionally substituted with substituent C, C1-C6 haloalkoxy group, substituted C3-C8 cycloalkoxy group optionally substituted with group C, C2-C6 alkenyloxy group optionally substituted with substituent C, C2-C6 haloalkenyloxy group optionally substituted with substituent C C3-C6 alkynyloxy group, C3-C6 haloalkynyloxy group, RaRbN- (wherein Ra and Rb are as defined above), Rc-L- (wherein Rc and L is as defined above.), RdC(=O)-(wherein Rd is as defined above), or RdC(=O)O-(wherein Rd is as defined above ).

Among them, R8 and R9 are each independently preferably a hydrogen atom, a cyano group, a halogen atom, a C1-C6 alkyl group optionally substituted with a substituent C, or a C1-C6 haloalkyl group,
In particular, R8 and R9 are each independently preferably a hydrogen atom or a halogen atom.

Preferable examples of each substituent of R8 and R9 are the same as those described for the substituent F.

R10 and R11 in formula (3) are each independently and specifically, a hydrogen atom, a hydroxyl group, a cyano group, a halogen atom, a C1 to C6 alkyl group optionally substituted with a substituent C, C1-C6 haloalkyl group, C3-C8 cycloalkyl group optionally substituted with substituent C, C2-C6 alkenyl group optionally substituted with substituent C, C2-C6 haloalkenyl group, substituted C2-C6 alkynyl group optionally substituted with group C, C2-C6 haloalkynyl group, C1-C6 alkoxy group optionally substituted with substituent C, C1-C6 haloalkoxy group, substituted C3-C8 cycloalkoxy group optionally substituted with group C, C2-C6 alkenyloxy group optionally substituted with substituent C, C2-C6 haloalkenyloxy group optionally substituted with substituent C C3-C6 alkynyloxy group, C3-C6 haloalkynyloxy group, RaRbN- (wherein Ra and Rb are as defined above), Rc-L- (wherein Rc and L is as defined above.), RdC(=O)-(wherein Rd is as defined above), or RdC(=O)O-(wherein Rd is as defined above ).

Among them, R10 and R11 are each independently a hydrogen atom, a cyano group, a halogen atom, a C1 to C6 alkyl group optionally substituted with a substituent C, a C1 to C6 haloalkyl group, or a substituent C as appropriate An optionally substituted C1 to C6 alkoxy group, a C2 to C6 alkenyloxy group optionally substituted by a substituent C, or a C3 to C6 alkynyloxy group optionally substituted by a substituent C are preferred. ,
In particular, R10 and R11 are each independently a hydrogen atom, a halogen atom, a C1-C6 alkyl group optionally substituted with a substituent C, or a C1-C6 optionally substituted with a substituent C Alkoxy groups are preferred.

Preferable examples of each substituent of R10 and R11 are the same as those described for the substituent F.

で表される。R4 and R5 in formula (1) together with the oxime structure (C=N-O) to form a benzisoxazole ring which may optionally be substituted 0 to 4 times with a substituent D (However, in the case of two or more substituents D, each is independent.) is represented by formula (4)

is represented by

In formula (4), R12, R13, R14 and R15 each independently represent a hydrogen atom or a substituent D, and R1, R2, X and Y are as defined above.

で表される。5,6-dihydro-4H-1 optionally substituted with 0 to 6 substituents F together with the oxime structure (C═N—O) to which R4 and R5 in formula (1) are attached , forming a 2-oxazine ring (however, in the case of two or more substituents F, each is independent) is represented by formula (5)

is represented by

In formula (5), R16, R17, R18, R19, R20 and R21 each independently represent a hydrogen atom or a substituent F, and R1, R2, X and Y are as defined above.

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— (where Ra and Rb has the same meaning as defined above) and Rc-L- (wherein Rc and L have the same meaning as defined above).

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

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

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

Substituent B represents at least one selected from the group consisting of a cyano group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group and a C3-C8 cycloalkoxy group.

Among them, the substituent B is preferably a cyano group or a C1-C6 alkoxy group.
Each term for the substituent B has the same meaning as defined above.

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

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

Substituent C 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. - (where Ra and Rb are as defined above), Rc-L- (wherein Rc and L are as defined above), RdC (=O) - (where Rd is as defined above), RdC(=O)O— (wherein Rd is as defined above) and a 3- to 6-membered ring group containing 1 to 2 oxygen atoms represents at least one selected from the group;

Among them, the substituent C 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, Rc-L- (here, Rc and L are as defined above.), RdC(=O)- (wherein Rd is as defined above), or RdC(=O)O- (wherein Rd is is synonymous with.) is preferred,
A hydroxyl group or RdC(=O)O- (wherein Rd has the same definition as above) is particularly preferred.

Each term for the substituent C has the same meaning as defined above. Pd in "RdC(=O)O-" is preferably a C1-C6 alkyl group optionally substituted with a substituent B or a C1-C6 haloalkyl group, more preferably C1-C6 is a haloalkyl group of

Preferred specific examples of the substituent C include a hydroxyl group; a cyano group;
cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl groups as C3-C8 cycloalkyl groups;
methoxy, ethoxy, propyloxy, isopropyloxy, butoxy, isobutoxy, and t-butoxy groups as C1-C6 alkoxy groups;
The C1 to C6 haloalkoxy groups include a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 3,3-difluoropropyloxy group, and a 3,3 , 3-trifluoropropyloxy group;
cyclopropyloxy, cyclobutoxy, cyclopentyloxy, and cyclohexyloxy groups as C3-C8 cycloalkoxy groups;
methoxymethoxy, ethoxymethoxy, methoxyethoxy, ethoxyethoxy, and methoxypropyloxy groups as C2-C6 alkoxyalkoxy groups;
RaRbN- (wherein Ra and Rb are as defined above) is an amino group, methylamino group, ethylamino group, propylamino group, isopropylamino group, (methoxymethyl)amino group, (2-methoxy ethyl)amino group, (cyanomethyl)amino group, (2-cyanoethyl)amino group, dimethylamino group, ethyl(methyl)amino group, methyl(propyl)amino group, isopropyl(methyl)amino group, (methoxymethyl)methylamino group, (2-methoxyethyl)methylamino group, (cyanomethyl)methylamino group, (2-cyanoethyl)methylamino group, diethylamino group, ethyl(propyl)amino group, ethyl(isopropyl)amino group, ethyl(methoxymethyl) amino group, ethyl(2-methoxyethyl)amino group, (cyanomethyl)ethylamino group, (2-cyanoethyl)ethylamino group, 2,2-difluoroethylamino group, 2,2,2-trifluoroethylamino group, cyclopropylamino group, (cyclopropyl)methylamino group, pyrrolidinyl group, and piperidinyl group;
Rc-L- (wherein Rc and L are as defined above), a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, a trifluoromethanesulfinyl group, and a trifluoromethanesulfonyl group;
RdC(=O)- (wherein Rd has the same definition as above) is 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, ethyl(methyl)aminocarbonyl group, diethylaminocarbonyl group, (methoxymethyl)methylaminocarbonyl group, (2-methoxyethyl)methylaminocarbonyl group, (cyanomethyl)methylaminocarbonyl group, (2-cyanoethyl)methyl aminocarbonyl group, 2,2-difluoroethylaminocarbonyl group, 2,2,2-trifluoroethylaminocarbonyl group, cyclopropylaminocarbonyl group, (cyclopropyl)methylaminocarbonyl group, pyrrolidinylcarbonyl group, and pyrrolidinylcarbonyl group; peridinylcarbonyl group;
RdC(=O)O- (wherein Rd has the same definition as above), a formyloxy group, an acetyloxy group, a methoxyacetyloxy group, a cyanoacetyloxy group, a propionyloxy group, a difluoroacetyloxy group, trifluoroacetyloxy group, cyclopropanecarbonyloxy 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)aminocarbonyl oxy group, (cyanomethyl)aminocarbonyloxy group, (2-cyanoethyl)aminocarbonyloxy group, dimethylaminocarbonyloxy group, ethyl(methyl)aminocarbonyloxy group, diethylaminocarbonyloxy group, (methoxymethyl)methylaminocarbonyloxy group , (2-methoxyethyl) methylaminocarbonyloxy group, (cyanomethyl) methylaminocarbonyloxy group, (2-cyanoethyl) methylaminocarbonyloxy group, 2,2-difluoroethylaminocarbonyloxy group, 2,2,2- a trifluoroethylaminocarbonyloxy group, a cyclopropylaminocarbonyloxy group, a cyclopropyl(methyl)aminocarbonyloxy group, a pyrrolidinylcarbonyloxy group, and a piperidinylcarbonyloxy group;
and 3- to 6-membered ring groups containing 1-2 oxygen atoms include oxolanyl, oxanyl, 1,3-dioxolanyl, and 1,3-dioxanyl groups.

More preferred specific examples of the substituent C include a hydroxyl group; a cyano group;
cyclopropyl group and cyclobutyl group as C3-C8 cycloalkyl groups;
Methoxy group and ethoxy group as C1 to C6 alkoxy groups;
difluoromethoxy, trifluoromethoxy, 2,2-difluoroethoxy, and 2,2,2-trifluoroethoxy groups as C1-C6 haloalkoxy groups;
C3-C8 cycloalkoxy groups, cyclopropyloxy group, cyclobutoxy group;
methoxymethoxy, ethoxymethoxy, methoxyethoxy, and ethoxyethoxy groups as C2-C6 alkoxyalkoxy groups;
RaRbN- (wherein Ra and Rb are as defined above), a dimethylamino group, an ethyl(methyl)amino group, and a diethylamino group;
Rc-L- (wherein Rc and L are as defined above), a methylthio group, a methanesulfinyl group, and a methanesulfonyl group;
RdC(=O)- (wherein Rd is as defined above) is a formyl group, an acetyl group, a methoxyacetyl group, a cyanoacetyl group, a difluoroacetyl group, a trifluoroacetyl group, a methoxycarbonyl group, an ethoxy carbonyl group, aminocarbonyl group, dimethylaminocarbonyl group, ethyl(methyl)aminocarbonyl group, and diethylaminocarbonyl group;
RdC(=O)O— (wherein Rd is as defined above), an acetyloxy group, a difluoroacetyloxy group, and a trifluoroacetyloxy group;
and 3- to 6-membered ring groups containing 1-2 oxygen atoms include 1,3-dioxolanyl and 1,3-dioxanyl groups.

Substituent D is a hydroxyl group, a cyano group, a nitro group, a halogen atom, a C1 to C6 alkyl group optionally substituted with a substituent B, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group, a C1 to represents at least one selected from the group consisting of a C6 alkoxy group, a C1-C6 haloalkoxy group and a C3-C8 cycloalkoxy group;

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

Each term of the substituent D has the same meaning as defined above. Regarding the "C1-C6 alkyl group optionally substituted with a substituent B", when the substituent B is present, the hydrogen atom in the C1-C6 alkyl group is optionally substituted with the substituent B. .

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

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

Substituent E is a hydroxyl group, a cyano group, a halogen atom, a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group, a C3-C8 optionally substituted with a substituent C A 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, a C2-C6 haloalkynyl group, C1-C6 alkoxy group optionally substituted with substituent C, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group optionally substituted with substituent C, substituent C C2-C6 alkenyloxy group optionally substituted with C2-C6 haloalkenyloxy group, C3-C6 alkynyloxy group optionally substituted with substituent C, C3-C6 haloalkynyloxy group , a C2-C6 alkoxyalkoxy group, RaRbN- (where Ra and Rb are as defined above), Rc-L- (wherein Rc and L are as defined above), RdC (=O)-(wherein Rd is as defined above), RdC(=O)O-(wherein Rd is as defined above), RgON=C(Rh)-( Here, Rg and Rh each independently represent a hydrogen atom or a C1-C6 alkyl group), RiRjRkSi- (wherein Ri, Rj and Rk each independently represent a C1-C6 represents an alkyl group) and at least one selected from the group consisting of a 3- to 6-membered ring group containing 1 to 2 oxygen atoms.

Among them, the substituent E is a cyano group, a halogen atom, a C1 to C6 alkyl group optionally substituted with a substituent C, a C1 to C6 haloalkyl group, a C3 to C8 optionally substituted with a 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 halo alkynyl group, RaRbN- (wherein Ra and Rb are as defined above), RdC(=O)- (wherein Rd is as defined above), RgON=C(Rh)- (wherein Rg and Rh are as defined above) and RiRjRkSi- (wherein Ri, Rj and Rk are as defined above) are preferred,
In particular, a halogen atom, a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group, a C2-C6 alkenyl group optionally substituted with a substituent C, a substituent C optionally An optionally substituted C2-C6 alkynyl group, RaRbN- (wherein Ra and Rb are as defined above), RdC(=O)- (wherein Rd is as defined above. ), RgON=C(Rh)- (wherein Rg and Rh are as defined above) and RiRjRkSi- (wherein Ri, Rj and Rk are as defined above).

Each term for the substituent E has the same meaning as defined above. Regarding the "C1-C6 alkyl group optionally substituted with a substituent C", when it has a substituent C, the hydrogen atom in the C1-C6 alkyl group is arbitrarily substituted with the substituent C. . With respect to the "C3-C8 cycloalkyl group optionally substituted with a substituent C", when having a substituent C, a hydrogen atom in the C3-C8 cycloalkyl group is optionally substituted with the substituent C . With respect to the “C2-C6 alkenyl group optionally substituted with a substituent C”, if the C2-C6 alkenyl group has a substituent C, a hydrogen atom in the C2-C6 alkenyl group is optionally substituted with the substituent C. With respect to the “C2-C6 alkynyl group optionally substituted with a substituent C”, when having a substituent C, a hydrogen atom in the C2-C6 alkynyl group is optionally substituted with the substituent C. With respect to the “C1-C6 alkoxy group optionally substituted with a substituent C”, when having a substituent C, a hydrogen atom in the C1-C6 alkoxy group is optionally substituted with the substituent C. With respect to the "C3-C8 cycloalkoxy group optionally substituted with a substituent C", when having a substituent C, a hydrogen atom in the C3-C8 cycloalkoxy group is optionally substituted with the substituent C . With respect to the "C2-C6 alkenyloxy group optionally substituted with a substituent C", when having a substituent C, a hydrogen atom in the C2-C6 alkenyloxy group is optionally substituted with the substituent C . With respect to the "C3-C6 alkynyloxy group optionally substituted with a substituent C", when having a substituent C, a hydrogen atom in the C3-C6 alkynyloxy group is optionally substituted with the substituent C .

Preferred specific examples of the substituent E include a hydroxyl group; a cyano group;
as halogen atoms, a fluorine atom, a chlorine atom, a bromine atom and an iodine atom;
Examples of C1 to C6 alkyl groups optionally substituted by substituent C include a methyl group, a hydroxymethyl group, a cyanomethyl group, a cyclopropylmethyl group, a cyclobutylmethyl group, a methoxymethyl group, an ethoxymethyl group, and a difluoromethoxymethyl group. , trifluoromethoxymethyl group, cyclopropyloxymethyl group, cyclobutyloxymethyl group, methoxymethoxymethyl group, dimethylaminomethyl group, methylthiomethyl group, methylsulfinylmethyl group, methylsulfonylmethyl group, acetylmethyl group, propionoyl methyl group, trifluoroacetylmethyl group, methoxycarbonylmethyl group, ethoxycarbonylmethyl group, acetyloxymethyl group, difluoroacetyloxymethyl group, trifluoroacetyloxymethyl group, (1,3-dioxolan-2-yl)methyl group , (1,3-dioxan-2-yl)methyl group, ethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 1-cyanoethyl group, 2-cyanoethyl group, 1-methoxyethyl group, 2-methoxyethyl group, 1-methoxyethyl group, 2-ethoxyethyl group, 1-difluoromethoxyethyl group, 2-difluoromethoxyethyl group, 1-trifluoromethoxyethyl group, 2-trifluoromethoxyethyl group, 1-methoxymethoxyethyl group , 2-methoxymethoxyethyl group, 2-(dimethylamino)ethyl group, 1-(methylthio)ethyl group, 2-(methylthio)ethyl group, 1-(methylsulfinyl)ethyl group, 2-(methylsulfinyl)ethyl group , 1-(methylsulfonyl)ethyl group, 2-(methylsulfonyl)ethyl group, 2-(acetyl)ethyl group, 2-(propionoyl)ethyl group, 2-(methoxycarbonyl)ethyl group, 2-(ethoxycarbonyl) ethyl group, 1-(acetyloxy)ethyl group, 2-(acetyloxy)ethyl group, 1-(difluoroacetyloxy)ethyl group, 2-(difluoroacetyloxy)ethyl group, 1-(trifluoroacetyloxy)ethyl group, 2-(trifluoroacetyloxy)ethyl group, 2-(1,3-dioxolan-2-yl)ethyl group, 2-(1,3-dioxan-2-yl)ethyl group, propyl group, 1- hydroxypropyl group, 2-hydroxypropyl group, 3-hydroxypropyl group, 1-cyanopropyl group, 2-cyanopropyl group, 3-cyanopropyl group, 1-methoxypropyl group, 2-methoxypropyl group group, 3-methoxypropyl group, 1-ethoxypropyl group, 2-ethoxypropyl group, 3-ethoxypropyl group, 1-(acetyloxy)propyl group, 2-(acetyloxy)propyl group, 3-(acetyloxy ) propyl group, 1-(difluoroacetyloxy) propyl group, 2-(difluoroacetyloxy) propyl group, 3-(difluoroacetyloxy) propyl group, 1-(trifluoroacetyloxy) propyl group, 2-(trifluoro acetyloxy)propyl group, 3-(trifluoroacetyloxy)propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, and t-butyl group;
C1 to C6 haloalkyl groups include monofluoromethyl group, difluoromethyl group, trifluoromethyl group, monochloromethyl group, monobromomethyl group, monoiodomethyl group, 2,2-difluoroethyl group, 2,2,2- a trifluoroethyl group, a 3,3-difluoropropyl group, and a 3,3,3-trifluoropropyl group;
Examples of C3-C8 cycloalkyl groups optionally substituted with substituent C include a cyclopropyl group, a 1-hydroxycyclopropyl group, a 1-cyanocyclopropyl group, a 2-cyclopropylcyclopropyl group and a 1-methoxychloropropyl group. group, 1-ethoxycyclopropyl group, cyclobutyl group, 1-hydroxycyclobutyl group, 1-cyanocyclobutyl group, 1-methoxycyclobutyl group, 1-ethoxycyclobutyl group, cyclopentyl group, 1-hydroxycyclopentyl group, 1 -cyanocyclopentyl group, 1-methoxynocyclopentyl group, 1-ethoxynocyclopentyl group, cyclohexyl group, 1-hydroxycyclohexyl group, 4-hydroxycyclohexyl group, 1-cyanocyclohexyl group, 1-methoxycyclohexyl group, 1-ethoxycyclohexyl group, 4-methoxycyclohexyl group, 4-ethoxycyclohexyl group, 4-difluoromethoxycyclohexyl group, 4-trifluoromethoxycyclohexyl group, 4-cyclopropyloxycyclohexyl group, 4-cyclobutyloxycyclohexyl group, 4-(methoxymethoxy ) cyclohexyl group, 4-(dimethylamino)cyclohexyl group, 4-(methylthio)cyclohexyl group, 4-(methylsulfinyl)cyclohexyl group, 4-(methylsulfonyl)cyclohexyl group, 4-acetylcyclohexyl group, 4-trifluoroacetyl cyclohexyl group, 4-acetyloxycyclohexyl group, 4-trifluoroacetyloxycyclohexyl group, 4-(1,3-dioxolan-2-yl)cyclohexyl group, and 4-(1,3-dioxan-2-yl)cyclohexyl group;
Examples of C2-C6 alkenyl groups optionally substituted with substituent C include vinyl group, 2-cyanovinyl group, 2-cyclopropylvinyl group, 2-methoxyvinyl group, 2-ethoxyvinyl group and 2-trifluoromethoxyvinyl. group, 2-cyclopropyloxyvinyl group, 2-(methoxymethoxy)vinyl group, 2-(dimethylamino)vinyl group, 2-acetylvinyl group, 2-(trifluoroacetyl)vinyl group, 2-(1,3 -dioxolan-2-yl)vinyl group, 2-(1,3-dioxan-2-yl)vinyl group, 1-propenyl group, 3-hydroxy-1-propenyl group, allyl group, 1-hydroxyallyl group, 1 -(methoxymethoxy) allyl group, 1-(methylthio) allyl group, 1-(methylsulfinyl) allyl group, 1-(methylsulfonyl) allyl group, 1-(acetyloxy) allyl group, 1-(difluoroacetyloxy) allyl group, 1-(trifluoroacetyloxy)allyl group, 1-butenyl group, 2-butenyl group, and 3-butenyl group;
The C2 to C6 haloalkenyl groups include 2-fluorovinyl, 2,2-difluorovinyl, 2,2-dichlorovinyl, 3-fluoroallyl, 3,3-difluoroallyl, and 3,3- dichloroallyl group;
Examples of C2-C6 alkynyl groups optionally substituted with substituent C include ethynyl group, 2-cyclopropylethynyl group, 2-cyclobutylethynyl group, 2-(acetyl)ethynyl group, and 2-(trifluoroacetyl). ethynyl group, 2-(1,3-dioxolan-2-yl) ethynyl group, 2-(1,3-dioxan-2-yl) ethynyl group, 1-propynyl group, propargyl group, 1-hydroxypropargyl group, 1 -cyanopropargyl group, 1-methoxypropargyl group, 1-ethoxypropargyl group, 1-(difluoromethoxy)propargyl group, 1-(trifluoromethoxy)propargyl group, 1-(dimethylamino)propargyl group, 1-(methylthio) propargyl group, 1-(methylsulfinyl)propargyl group, 1-(methylsulfonyl)propargyl group, 1-(acetyloxy)propargyl group, 1-(trifluoroacetyloxy)propargyl group, 1-butynyl group, 2-butynyl group , and a 3-butynyl group;
C2 to C6 haloalkynyl groups include 3,3-difluoro-1-propynyl group, 3,3,3-trifluoro-1-propynyl group, 4,4-difluoro-1-butynyl group, 4,4-difluoro -2-butynyl group, 4,4,4-trifluoro-1-butynyl group, and 4,4,4-trifluoro-2-butynyl group;
Examples of C1 to C6 alkoxy groups optionally substituted by substituent C include methoxy group, cyanomethoxy group, cyclopropylmethoxy group, cyclobutylmethoxy group, methoxymethoxy group, ethoxymethoxy group, difluoromethoxymethoxy group, trifluoro methoxymethoxy group, cyclopropyloxymethoxy group, cyclobutyloxymethoxy group, methylthiomethoxy group, methylsulfinylmethoxy group, methylsulfonylmethoxy group, acetylmethoxy group, propionoylmethoxy group, trifluoroacetylmethoxy group, methoxycarbonylmethoxy group , ethoxycarbonylmethoxy group, acetyloxymethoxy group, difluoroacetyloxymethoxy group, trifluoroacetyloxymethoxy group, (1,3-dioxolan-2-yl)methoxy group, (1,3-dioxan-2-yl)methoxy group, ethoxy group, 2-hydroxyethoxy group, 1-cyanoethoxy group, 2-cyanoethoxy group, 2-methoxyethoxy group, 2-ethoxyethoxy group, 1-difluoromethoxyethoxy group, 2-difluoromethoxyethoxy group, 1 -trifluoromethoxyethoxy group, 2-trifluoromethoxyethoxy group, 2-methoxymethoxyethoxy group, 2-(dimethylamino) ethoxy group, 1-(methylthio) ethoxy group, 2-(methylthio) ethoxy group, 1-( methylsulfinyl)ethoxy group, 2-(methylsulfinyl)ethoxy group, 1-(methylsulfonyl)ethoxy group, 2-(methylsulfonyl)ethoxy group, 2-(acetyl)ethoxy group, 2-(propionoyl)ethoxy group, 2 -(methoxycarbonyl) ethoxy group, 2-(ethoxycarbonyl) ethoxy group, 1-(acetyloxy) ethoxy group, 2-(acetyloxy) ethoxy group, 1-(difluoroacetyloxy) ethoxy group, 2-(difluoroacetyl oxy)ethoxy group, 1-(trifluoroacetyloxy)ethoxy group, 2-(trifluoroacetyloxy)ethoxy group, 2-(1,3-dioxolan-2-yl)ethoxy group, 2-(1,3- dioxan-2-yl) ethoxy group, propyloxy group, 2-hydroxypropyloxy group, 3-hydroxypropyloxy group, 1-(acetyloxy) propyloxy group, 2-(acetyloxy) propyloxy group, 3-( acetyloxy) propyloxy group, 1-(difluoroacetyloxy) propyloxy group, 2-( difluoroacetyloxy) propyloxy group, 3-(difluoroacetyloxy) propyloxy group, 1-(trifluoroacetyloxy) propyloxy group, 2-(trifluoroacetyloxy) propyloxy group, 3-(trifluoroacetyloxy) ) propyloxy, isopropyloxy, butyloxy, isobutyloxy, sec-butyloxy, and t-butyloxy groups;
The C1 to C6 haloalkoxy groups include a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 3,3-difluoropropyloxy group, and a 3,3 , 3-trifluoropropyloxy group;
Examples of the C3-C8 cycloalkoxy group optionally substituted with substituent C include a cyclopropyloxy group, a 1-cyanocyclopropyloxy group, a 2-cyclopropylcyclopropyloxy group, a cyclobutyloxy group and a 1-cyanocyclo butyloxy group, cyclopentyloxy group, 1-cyanocyclopentyloxy group, cyclohexyloxy group, 4-hydroxycyclohexyloxy group, 1-cyanocyclohexyloxy group, 4-methoxycyclohexyloxy group, 4-ethoxycyclohexyloxy group, 4-difluoro methoxycyclohexyloxy group, 4-trifluoromethoxycyclohexyloxy group, 4-cyclopropyloxycyclohexyloxy group, 4-cyclobutyloxycyclohexyloxy group, 4-(methoxymethoxy)cyclohexyloxy group, 4-(dimethylamino)cyclohexyloxy group, 4-(methylthio)cyclohexyloxy group, 4-(methylsulfinyl)cyclohexyloxy group, 4-(methylsulfonyl)cyclohexyloxy group, 4-acetylcyclohexyloxy group, 4-trifluoroacetylcyclohexyloxy group, 4-acetyl oxycyclohexyloxy group, 4-trifluoroacetyloxycyclohexyloxy group, 4-(1,3-dioxolan-2-yl)cyclohexyloxy group, and 4-(1,3-dioxan-2-yl)cyclohexyloxy group;
Examples of C2 to C6 alkenyloxy groups which may be optionally substituted with a substituent C include a vinyloxy group, a 2-cyanovinyloxy group, a 2-cyclopropylvinyloxy group, a 2-methoxyvinyloxy group and a 2-ethoxyvinyloxy group. , 2-trifluoromethoxyvinyloxy group, 2-cyclopropyloxyvinyloxy group, 2-(methoxymethoxy)vinyloxy group, 2-(dimethylamino)vinyloxy group, 2-acetylvinyloxy group, 2-(trifluoroacetyl ) vinyloxy group, 2-(1,3-dioxolan-2-yl) vinyloxy group, 2-(1,3-dioxan-2-yl) vinyloxy group, 1-propenyloxy group, 3-hydroxy-1-propenyloxy group, allyloxy group, 1-(methoxymethoxy)allyloxy group, 1-(methylthio)allyloxy group, 1-(methylsulfinyl)allyloxy group, 1-(methylsulfonyl)allyloxy group, 1-(acetyloxy)allyloxy group, 1 -(difluoroacetyloxy) allyloxy group, 1-(trifluoroacetyloxy) allyloxy group, 1-butenyloxy group, 2-butenyloxy group, and 3-butenyloxy group;
C2 to C6 haloalkenyloxy groups include 2-fluorovinyloxy, 2,2-difluorovinyloxy, 2,2-dichlorovinyloxy, 3-fluoroallyloxy, and 3,3-difluoroallyloxy groups , and a 3,3-dichloroallyloxy group;
Examples of the C3-C6 alkynyloxy group optionally substituted with a substituent C include a propargyloxy group, a 3-(cyclopropyl)propargyloxy group, a 3-(cyclobutyl)propargyloxy group, and a 3-(acetyl)propargyloxy group. , 3-(difluoroacetyl) propargyloxy group, 3-(trifluoroacetyl) propargyloxy group, 3-(1,3-dioxolan-2-yl) propargyloxy group, 3-(1,3-dioxane-2- yl) propargyloxy group, 2-butynyloxy group, 4-hydroxy-2-butynyloxy group, 4-cyano-2-butynyloxy group, 4-methoxy-2-butynyloxy group, 4-ethoxy-2-butynyloxy group, 4-difluoro methoxy-2-butynyloxy group, 4-trifluoromethoxy-2-butynyloxy group, 4-cyclopropyloxy-2-butynyloxy group, 4-cyclobutyloxy-2-butynyloxy group, 4-methoxymethoxy-2-butynyloxy group, 4-dimethylamino-2-butynyloxy group, 4-pyrrolidino-2-butynyloxy group, 4-piperidino-2-butynyloxy group, 4-pyrrolidino-2-butynyloxy group, 4-methylthio-2-butynyloxy group, 4-methylsulfinyl -2-butynyloxy group, 4-methylsulfonyl-2-butynyloxy group, 4-acetyloxy-2-butynyloxy group, 4-trifluoroacetyloxy-2-butynyloxy group, and 3-butynyloxy group;
C3-C6 haloalkynyloxy groups, 4,4-difluoro-2-butynyloxy group, 4-chloro-4,4-difluoro-2-butynyloxy group, 4-bromo-4,4-difluoro-2-butynyloxy group , and a 4,4,4-trifluoro-2-butynyloxy group;
methoxymethoxy, ethoxymethoxy, methoxyethoxy, ethoxyethoxy, and methoxypropyloxy groups as C2-C6 alkoxyalkoxy groups;
RaRbN- (wherein Ra and Rb are as defined above) is an amino group, methylamino group, ethylamino group, propylamino group, isopropylamino group, (methoxymethyl)amino group, (2-methoxy ethyl)amino group, (cyanomethyl)amino group, (2-cyanoethyl)amino group, dimethylamino group, ethyl(methyl)amino group, methyl(propyl)amino group, isopropyl(methyl)amino group, (methoxymethyl)methylamino group, (2-methoxyethyl)methylamino group, (cyanomethyl)methylamino group, (2-cyanoethyl)methylamino group, diethylamino group, ethyl(propyl)amino group, ethyl(isopropyl)amino group, ethyl(methoxymethyl) amino group, ethyl(2-methoxyethyl)amino group, (cyanomethyl)ethylamino group, (2-cyanoethyl)ethylamino group, 2,2-difluoroethylamino group, 2,2,2-trifluoroethylamino group, cyclopropylamino group, (cyclopropyl)methylamino group, pyrrolidinyl group, and piperidinyl group;
Rc-L- (wherein Rc and L are as defined above), a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, a trifluoromethanesulfinyl group, and a trifluoromethanesulfonyl group;
RdC(=O)- (wherein Rd has the same definition as above) is 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, ethyl(methyl)aminocarbonyl group, diethylaminocarbonyl group, (methoxymethyl)methylaminocarbonyl group, (2-methoxyethyl)methylaminocarbonyl group, (cyanomethyl)methylaminocarbonyl group, (2-cyanoethyl)methyl aminocarbonyl group, 2,2-difluoroethylaminocarbonyl group, 2,2,2-trifluoroethylaminocarbonyl group, cyclopropylaminocarbonyl group, (cyclopropyl)methylaminocarbonyl group, pyrrolidinylcarbonyl group, and pyrrolidinylcarbonyl group; peridinylcarbonyl group;
RdC(=O)O- (wherein Rd has the same definition as above), a formyloxy group, an acetyloxy group, a methoxyacetyloxy group, a cyanoacetyloxy group, a propionyloxy group, a difluoroacetyloxy group, trifluoroacetyloxy group, cyclopropanecarbonyloxy 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)aminocarbonyl oxy group, (cyanomethyl)aminocarbonyloxy group, (2-cyanoethyl)aminocarbonyloxy group, dimethylaminocarbonyloxy group, ethyl(methyl)aminocarbonyloxy group, diethylaminocarbonyloxy group, (methoxymethyl)methylaminocarbonyloxy group , (2-methoxyethyl) methylaminocarbonyloxy group, (cyanomethyl) methylaminocarbonyloxy group, (2-cyanoethyl) methylaminocarbonyloxy group, 2,2-difluoroethylaminocarbonyloxy group, 2,2,2- a trifluoroethylaminocarbonyloxy group, a cyclopropylaminocarbonyloxy group, a cyclopropyl(methyl)aminocarbonyloxy group, a pyrrolidinylcarbonyloxy group, and a piperidinylcarbonyloxy group;
RgON=C(Rh)- (wherein Rg and Rh are as defined above), a (hydroxyimino)methyl group, a 1-(hydroxyimino)ethyl group, a 1-(hydroxyimino)propyl group, 1-(hydroxyimino)butyl group, (methoxyimino)methyl group, 1-(methoxyimino)ethyl group, 1-(methoxyimino)propyl group, 1-(methoxyimino)butyl group, (ethoxyimino)methyl group, 1-(ethoxyimino) ethyl group, 1-(ethoxyimino) propyl group, 1-(ethoxyimino) butyl group, (propyloxyimino) methyl group, 1-(propyloxyimino) ethyl group, 1-(propyloxy imino)propyl group, 1-(propyloxyimino)butyl group, (isopropyloxyimino)methyl group, 1-(isopropyloxyimino)ethyl group, 1-(isopropyloxyimino)propyl group, and 1-(isopropyloxyimino) ) butyl group;
RiRjRkSi- (wherein Ri, Rj and Rk are as defined above), a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, and a triisopropylsilyl group;
and 3- to 6-membered ring groups containing 1-2 oxygen atoms include oxolanyl, oxanyl, 1,3-dioxolanyl, and 1,3-dioxanyl groups.

More preferred specific examples of the substituent E include a hydroxyl group; a cyano group;
as halogen atoms, a chlorine atom, a bromine atom and an iodine atom;
Examples of C1 to C6 alkyl groups optionally substituted by substituent C include methyl group, hydroxymethyl group, methoxymethyl group, acetyloxymethyl group, difluoroacetyloxymethyl group, trifluoroacetyloxymethyl group, ethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 1-methoxyethyl group, 1-(acetyloxy)ethyl group, 2-(acetyloxy)ethyl group, 1-(difluoroacetyloxy)ethyl group, 2-(difluoro acetyloxy)ethyl group, 1-(trifluoroacetyloxy)ethyl group, 2-(trifluoroacetyloxy)ethyl group, propyl group, and isopropyl group;
a monobromomethyl group, a difluoromethyl group, and a trifluoromethyl group as the C1 to C6 haloalkyl groups;
cyclopropyl group, cyclobutyl group, and cyclopentyl group as C3-C8 cycloalkyl groups optionally substituted with substituent C;
C2-C6 alkenyl groups optionally substituted with a substituent C include a vinyl group, a 1-propenyl group, and an allyl group;
2-fluorovinyl group and 2,2-difluorovinyl group as C2-C6 haloalkenyl groups;
Ethynyl group, 1-propynyl group, and propargyl group as C2-C6 alkynyl groups optionally substituted with substituent C;
3,3-difluoro-1-propynyl group and 3,3,3-trifluoro-1-propynyl group as C2-C6 haloalkynyl groups;
Examples of C1 to C6 alkoxy groups optionally substituted with substituent C include a methoxy group, a cyanomethoxy group, a methoxymethoxy group, a methylthiomethoxy group, a methylsulfinylmethoxy group, a methylsulfonylmethoxy group, an ethoxy group, and 1-cyanoethoxy. 2-cyanoethoxy, 2-methoxyethoxy, propyloxy, isopropyloxy, butyloxy, isobutyloxy, sec-butyloxy, and t-butyloxy groups;
difluoromethoxy, trifluoromethoxy, 2,2-difluoroethoxy, and 2,2,2-trifluoroethoxy groups as C1-C6 haloalkoxy groups;
C3-C8 cycloalkoxy groups optionally substituted with a substituent C include a cyclopropyloxy group, a cyclobutyloxy group and a cyclopentyloxy group;
C2-C6 alkenyloxy groups optionally substituted with substituent C include vinyloxy, 1-propenyloxy, and allyloxy groups;
2-fluorovinyloxy and 2,2-difluorovinyloxy as C2-C6 haloalkenyloxy groups;
A propargyloxy group as the C3-C6 alkynyloxy group optionally substituted with a substituent C;
4,4-difluoro-2-butynyloxy group as the C3-C6 haloalkynyloxy group;
methoxymethoxy, ethoxymethoxy, methoxyethoxy, and ethoxyethoxy groups as C2-C6 alkoxyalkoxy groups;
RaRbN- (wherein Ra and Rb are as defined above), an amino group, a dimethylamino group, an ethyl(methyl)amino group, and a diethylamino group;
Rc-L- (wherein Rc and L are as defined above), a methylthio group, a methanesulfinyl group, and a methanesulfonyl group;
RdC(=O)- (wherein Rd is as defined above), a formyl group, an acetyl group, a methoxyacetyl group, a cyanoacetyl group, a difluoroacetyl group, and a trifluoroacetyl group;
RdC(=O)O- (wherein Rd has the same definition as above) is an acetyloxy group, methoxyacetyloxy group, cyanoacetyloxy group, difluoroacetyloxy group, trifluoroacetyloxy group, methoxycarbonyl oxy group, ethoxycarbonyloxy group, aminocarbonyloxy group, dimethylaminocarbonyloxy group, ethyl(methyl)aminocarbonyloxy group, and diethylaminocarbonyloxy group;
RgON=C(Rh)- (where Rg and Rh are as defined above) are (hydroxyimino)methyl group, 1-(hydroxyimino)ethyl group, (methoxyimino)methyl group, 1- (methoxyimino) ethyl group, (ethoxyimino) methyl group, 1-(ethoxyimino) ethyl group, (propyloxyimino) methyl group, 1-(propyloxyimino) ethyl group, (isopropyloxyimino) methyl group, and 1-(isopropyloxyimino) ethyl group;
RiRjRkSi- (wherein Ri, Rj and Rk are as defined above), a trimethylsilyl group and a triethylsilyl group;
and 3- to 6-membered ring groups containing 1-2 oxygen atoms include 1,3-dioxolanyl and 1,3-dioxanyl groups.

Substituent F is a hydroxyl group, a cyano group, a halogen atom, a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group, a C3-C8 optionally substituted with a substituent C. A 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, a C2-C6 haloalkynyl group, C1-C6 alkoxy group optionally substituted with substituent C, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group optionally substituted with substituent C, substituent C C2-C6 alkenyloxy group optionally substituted with C2-C6 haloalkenyloxy group, C3-C6 alkynyloxy group optionally substituted with substituent C, C3-C6 haloalkynyloxy group , RaRbN- (wherein Ra and Rb are as defined above), Rc-L- (wherein Rc and L are as defined above), RdC (=O)- (where , Rd has the same meaning as defined above) and RdC(=O)O- (wherein Rd has the same meaning as defined above).

Among them, the substituent F is a hydroxyl group, a cyano group, a halogen atom, a C1 to C6 alkyl group optionally substituted with a substituent C, a C1 to C6 haloalkyl group optionally substituted with a substituent C, a C3 to C8 cycloalkyl group, C1-C6 alkoxy group optionally substituted with substituent C, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group optionally substituted with substituent C, RdC (=O)- (wherein Rd is as defined above) and RdC(=O)O- (wherein Rd is as defined above) are preferred,
In particular, a halogen atom, a C1-C6 alkyl group optionally substituted with a substituent C, and a C1-C6 alkoxy group optionally substituted with a substituent C are preferred.

Each term for the substituent F has the same meaning as defined above. Regarding the "C1-C6 alkyl group optionally substituted with a substituent C", when it has a substituent C, the hydrogen atom in the C1-C6 alkyl group is arbitrarily substituted with the substituent C. . With respect to the "C3-C8 cycloalkyl group optionally substituted with a substituent C", when having a substituent C, a hydrogen atom in the C3-C8 cycloalkyl group is optionally substituted with the substituent C . With respect to the “C2-C6 alkenyl group optionally substituted with a substituent C”, if the C2-C6 alkenyl group has a substituent C, a hydrogen atom in the C2-C6 alkenyl group is optionally substituted with the substituent C. With respect to the “C2-C6 alkynyl group optionally substituted with a substituent C”, when the substituent C is present, a hydrogen atom in the C2-C6 alkynyl group is optionally substituted with the substituent C.
With respect to the "C1-C6 alkoxy group optionally substituted with a substituent C", when having a substituent C, a hydrogen atom in the C1-C6 alkoxy group optionally substituted with a substituent C is substituted optionally substituted by group C; With respect to the "C3-C8 cycloalkoxy group optionally substituted with a substituent C", when having a substituent C, a hydrogen atom in the C3-C8 cycloalkoxy group is optionally substituted with the substituent C . With respect to the "C2-C6 alkenyloxy group optionally substituted with a substituent C", when having a substituent C, a hydrogen atom in the C2-C6 alkenyloxy group is optionally substituted with the substituent C . With respect to the "C3-C6 alkynyloxy group optionally substituted with a substituent C", when having a substituent C, a hydrogen atom in the C3-C6 alkynyloxy group is optionally substituted with the substituent C .

Preferred specific examples of the substituent F include a hydroxyl group; a cyano group;
as halogen atoms, a fluorine atom, a chlorine atom, a bromine atom and an iodine atom;
Examples of C1 to C6 alkyl groups optionally substituted by substituent C include a methyl group, a hydroxymethyl group, a cyanomethyl group, a cyclopropylmethyl group, a cyclobutylmethyl group, a methoxymethyl group, an ethoxymethyl group, and a difluoromethoxymethyl group. , trifluoromethoxymethyl group, cyclopropyloxymethyl group, cyclobutyloxymethyl group, methoxymethoxymethyl group, dimethylaminomethyl group, methylthiomethyl group, methylsulfinylmethyl group, methylsulfonylmethyl group, acetylmethyl group, propionoyl methyl group, trifluoroacetylmethyl group, methoxycarbonylmethyl group, ethoxycarbonylmethyl group, acetyloxymethyl group, difluoroacetyloxymethyl group, trifluoroacetyloxymethyl group, (1,3-dioxolan-2-yl)methyl group , (1,3-dioxan-2-yl)methyl group, ethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 1-cyanoethyl group, 2-cyanoethyl group, 1-methoxyethyl group, 2-methoxyethyl group, 1-methoxyethyl group, 2-ethoxyethyl group, 1-difluoromethoxyethyl group, 2-difluoromethoxyethyl group, 1-trifluoromethoxyethyl group, 2-trifluoromethoxyethyl group, 1-methoxymethoxyethyl group , 2-methoxymethoxyethyl group, 2-(dimethylamino)ethyl group, 1-(methylthio)ethyl group, 2-(methylthio)ethyl group, 1-(methylsulfinyl)ethyl group, 2-(methylsulfinyl)ethyl group , 1-(methylsulfonyl)ethyl group, 2-(methylsulfonyl)ethyl group, 2-(acetyl)ethyl group, 2-(propionoyl)ethyl group, 2-(methoxycarbonyl)ethyl group, 2-(ethoxycarbonyl) ethyl group, 1-(acetyloxy)ethyl group, 2-(acetyloxy)ethyl group, 1-(difluoroacetyloxy)ethyl group, 2-(difluoroacetyloxy)ethyl group, 1-(trifluoroacetyloxy)ethyl group, 2-(trifluoroacetyloxy)ethyl group, 2-(1,3-dioxolan-2-yl)ethyl group, 2-(1,3-dioxan-2-yl)ethyl group, propyl group, 1- hydroxypropyl group, 2-hydroxypropyl group, 3-hydroxypropyl group, 1-cyanopropyl group, 2-cyanopropyl group, 3-cyanopropyl group, 1-methoxypropyl group, 2-methoxypropyl group group, 3-methoxypropyl group, 1-ethoxypropyl group, 2-ethoxypropyl group, 3-ethoxypropyl group, 1-(acetyloxy)propyl group, 2-(acetyloxy)propyl group, 3-(acetyloxy ) propyl group, 1-(difluoroacetyloxy) propyl group, 2-(difluoroacetyloxy) propyl group, 3-(difluoroacetyloxy) propyl group, 1-(trifluoroacetyloxy) propyl group, 2-(trifluoro acetyloxy)propyl group, 3-(trifluoroacetyloxy)propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, and t-butyl group;
C1 to C6 haloalkyl groups include monofluoromethyl group, difluoromethyl group, trifluoromethyl group, monochloromethyl group, monobromomethyl group, monoiodomethyl group, 2,2-difluoroethyl group, 2,2,2- a trifluoroethyl group, a 3,3-difluoropropyl group, and a 3,3,3-trifluoropropyl group;
Examples of C3-C8 cycloalkyl groups optionally substituted with substituent C include a cyclopropyl group, a 1-hydroxycyclopropyl group, a 1-cyanocyclopropyl group, a 2-cyclopropylcyclopropyl group and a 1-methoxychloropropyl group. group, 1-ethoxycyclopropyl group, cyclobutyl group, 1-hydroxycyclobutyl group, 1-cyanocyclobutyl group, 1-methoxycyclobutyl group, 1-ethoxycyclobutyl group, cyclopentyl group, 1-hydroxycyclopentyl group, 1 -cyanocyclopentyl group, 1-methoxynocyclopentyl group, 1-ethoxynocyclopentyl group, cyclohexyl group, 1-hydroxycyclohexyl group, 4-hydroxycyclohexyl group, 1-cyanocyclohexyl group, 1-methoxycyclohexyl group, 1-ethoxycyclohexyl group, 4-methoxycyclohexyl group, 4-ethoxycyclohexyl group, 4-difluoromethoxycyclohexyl group, 4-trifluoromethoxycyclohexyl group, 4-cyclopropyloxycyclohexyl group, 4-cyclobutyloxycyclohexyl group, 4-(methoxymethoxy ) cyclohexyl group, 4-(dimethylamino)cyclohexyl group, 4-(methylthio)cyclohexyl group, 4-(methylsulfinyl)cyclohexyl group, 4-(methylsulfonyl)cyclohexyl group, 4-acetylcyclohexyl group, 4-trifluoroacetyl cyclohexyl group, 4-acetyloxycyclohexyl group, 4-trifluoroacetyloxycyclohexyl group, 4-(1,3-dioxolan-2-yl)cyclohexyl group, and 4-(1,3-dioxan-2-yl)cyclohexyl group;
Examples of C2-C6 alkenyl groups optionally substituted with substituent C include vinyl group, 2-cyanovinyl group, 2-cyclopropylvinyl group, 2-methoxyvinyl group, 2-ethoxyvinyl group and 2-trifluoromethoxyvinyl. group, 2-cyclopropyloxyvinyl group, 2-(methoxymethoxy)vinyl group, 2-(dimethylamino)vinyl group, 2-acetylvinyl group, 2-(trifluoroacetyl)vinyl group, 2-(1,3 -dioxolan-2-yl)vinyl group, 2-(1,3-dioxan-2-yl)vinyl group, 1-propenyl group, 3-hydroxy-1-propenyl group, allyl group, 1-hydroxyallyl group, 1 -(methoxymethoxy) allyl group, 1-(methylthio) allyl group, 1-(methylsulfinyl) allyl group, 1-(methylsulfonyl) allyl group, 1-(acetyloxy) allyl group, 1-(difluoroacetyloxy) allyl group, 1-(trifluoroacetyloxy)allyl group, 1-butenyl group, 2-butenyl group, and 3-butenyl group;
The C2 to C6 haloalkenyl groups include 2-fluorovinyl, 2,2-difluorovinyl, 2,2-dichlorovinyl, 3-fluoroallyl, 3,3-difluoroallyl, and 3,3- dichloroallyl group;
Examples of C2-C6 alkynyl groups optionally substituted with substituent C include ethynyl group, 2-cyclopropylethynyl group, 2-cyclobutylethynyl group, 2-(acetyl)ethynyl group, and 2-(trifluoroacetyl). ethynyl group, 2-(1,3-dioxolan-2-yl) ethynyl group, 2-(1,3-dioxan-2-yl) ethynyl group, 1-propynyl group, propargyl group, 1-hydroxypropargyl group, 1 -cyanopropargyl group, 1-methoxypropargyl group, 1-ethoxypropargyl group, 1-(difluoromethoxy)propargyl group, 1-(trifluoromethoxy)propargyl group, 1-(dimethylamino)propargyl group, 1-(methylthio) propargyl group, 1-(methylsulfinyl)propargyl group, 1-(methylsulfonyl)propargyl group, 1-(acetyloxy)propargyl group, 1-(trifluoroacetyloxy)propargyl group, 1-butynyl group, 2-butynyl group , and a 3-butynyl group;
C2 to C6 haloalkynyl groups include 3,3-difluoro-1-propynyl group, 3,3,3-trifluoro-1-propynyl group, 4,4-difluoro-1-butynyl group, 4,4-difluoro -2-butynyl group, 4,4,4-trifluoro-1-butynyl group, and 4,4,4-trifluoro-2-butynyl group;
Examples of C1 to C6 alkoxy groups optionally substituted by substituent C include methoxy group, cyanomethoxy group, cyclopropylmethoxy group, cyclobutylmethoxy group, methoxymethoxy group, ethoxymethoxy group, difluoromethoxymethoxy group, trifluoro methoxymethoxy group, cyclopropyloxymethoxy group, cyclobutyloxymethoxy group, methylthiomethoxy group, methylsulfinylmethoxy group, methylsulfonylmethoxy group, acetylmethoxy group, propionoylmethoxy group, trifluoroacetylmethoxy group, methoxycarbonylmethoxy group , ethoxycarbonylmethoxy group, acetyloxymethoxy group, difluoroacetyloxymethoxy group, trifluoroacetyloxymethoxy group, (1,3-dioxolan-2-yl)methoxy group, (1,3-dioxan-2-yl)methoxy group, ethoxy group, 2-hydroxyethoxy group, 1-cyanoethoxy group, 2-cyanoethoxy group, 2-methoxyethoxy group, 2-ethoxyethoxy group, 1-difluoromethoxyethoxy group, 2-difluoromethoxyethoxy group, 1 -trifluoromethoxyethoxy group, 2-trifluoromethoxyethoxy group, 2-methoxymethoxyethoxy group, 2-(dimethylamino) ethoxy group, 1-(methylthio) ethoxy group, 2-(methylthio) ethoxy group, 1-( methylsulfinyl)ethoxy group, 2-(methylsulfinyl)ethoxy group, 1-(methylsulfonyl)ethoxy group, 2-(methylsulfonyl)ethoxy group, 2-(acetyl)ethoxy group, 2-(propionoyl)ethoxy group, 2 -(methoxycarbonyl) ethoxy group, 2-(ethoxycarbonyl) ethoxy group, 1-(acetyloxy) ethoxy group, 2-(acetyloxy) ethoxy group, 1-(difluoroacetyloxy) ethoxy group, 2-(difluoroacetyl oxy)ethoxy group, 1-(trifluoroacetyloxy)ethoxy group, 2-(trifluoroacetyloxy)ethoxy group, 2-(1,3-dioxolan-2-yl)ethoxy group, 2-(1,3- dioxan-2-yl) ethoxy group, propyloxy group, 2-hydroxypropyloxy group, 3-hydroxypropyloxy group, 1-(acetyloxy) propyloxy group, 2-(acetyloxy) propyloxy group, 3-( acetyloxy) propyloxy group, 1-(difluoroacetyloxy) propyloxy group, 2-( difluoroacetyloxy) propyloxy group, 3-(difluoroacetyloxy) propyloxy group, 1-(trifluoroacetyloxy) propyloxy group, 2-(trifluoroacetyloxy) propyloxy group, 3-(trifluoroacetyloxy) ) propyloxy, isopropyloxy, butyloxy, isobutyloxy, sec-butyloxy, and t-butyloxy groups;
The C1 to C6 haloalkoxy groups include a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 3,3-difluoropropyloxy group, and a 3,3 , 3-trifluoropropyloxy group;
Examples of the C3-C8 cycloalkoxy group optionally substituted with substituent C include a cyclopropyloxy group, a 1-cyanocyclopropyloxy group, a 2-cyclopropylcyclopropyloxy group, a cyclobutyloxy group and a 1-cyanocyclo butyloxy group, cyclopentyloxy group, 1-cyanocyclopentyloxy group, cyclohexyloxy group, 4-hydroxycyclohexyloxy group, 1-cyanocyclohexyloxy group, 4-methoxycyclohexyloxy group, 4-ethoxycyclohexyloxy group, 4-difluoro methoxycyclohexyloxy group, 4-trifluoromethoxycyclohexyloxy group, 4-cyclopropyloxycyclohexyloxy group, 4-cyclobutyloxycyclohexyloxy group, 4-(methoxymethoxy)cyclohexyloxy group, 4-(dimethylamino)cyclohexyloxy group, 4-(methylthio)cyclohexyloxy group, 4-(methylsulfinyl)cyclohexyloxy group, 4-(methylsulfonyl)cyclohexyloxy group, 4-acetylcyclohexyloxy group, 4-trifluoroacetylcyclohexyloxy group, 4-acetyl oxycyclohexyloxy group, 4-trifluoroacetyloxycyclohexyloxy group, 4-(1,3-dioxolan-2-yl)cyclohexyloxy group, and 4-(1,3-dioxan-2-yl)cyclohexyloxy group;
Examples of C2 to C6 alkenyloxy groups which may be optionally substituted with a substituent C include a vinyloxy group, a 2-cyanovinyloxy group, a 2-cyclopropylvinyloxy group, a 2-methoxyvinyloxy group and a 2-ethoxyvinyloxy group. , 2-trifluoromethoxyvinyloxy group, 2-cyclopropyloxyvinyloxy group, 2-(methoxymethoxy)vinyloxy group, 2-(dimethylamino)vinyloxy group, 2-acetylvinyloxy group, 2-(trifluoroacetyl ) vinyloxy group, 2-(1,3-dioxolan-2-yl) vinyloxy group, 2-(1,3-dioxan-2-yl) vinyloxy group, 1-propenyloxy group, 3-hydroxy-1-propenyloxy group, allyloxy group, 1-(methoxymethoxy)allyloxy group, 1-(methylthio)allyloxy group, 1-(methylsulfinyl)allyloxy group, 1-(methylsulfonyl)allyloxy group, 1-(acetyloxy)allyloxy group, 1 -(difluoroacetyloxy) allyloxy group, 1-(trifluoroacetyloxy) allyloxy group, 1-butenyloxy group, 2-butenyloxy group, and 3-butenyloxy group;
C2 to C6 haloalkenyloxy groups include 2-fluorovinyloxy, 2,2-difluorovinyloxy, 2,2-dichlorovinyloxy, 3-fluoroallyloxy, and 3,3-difluoroallyloxy groups , and a 3,3-dichloroallyloxy group;
Examples of the C3-C6 alkynyloxy group optionally substituted with a substituent C include a propargyloxy group, a 3-(cyclopropyl)propargyloxy group, a 3-(cyclobutyl)propargyloxy group, and a 3-(acetyl)propargyloxy group. , 3-(difluoroacetyl) propargyloxy group, 3-(trifluoroacetyl) propargyloxy group, 3-(1,3-dioxolan-2-yl) propargyloxy group, 3-(1,3-dioxane-2- yl) propargyloxy group, 2-butynyloxy group, 4-hydroxy-2-butynyloxy group, 4-cyano-2-butynyloxy group, 4-methoxy-2-butynyloxy group, 4-ethoxy-2-butynyloxy group, 4-difluoro methoxy-2-butynyloxy group, 4-trifluoromethoxy-2-butynyloxy group, 4-cyclopropyloxy-2-butynyloxy group, 4-cyclobutyloxy-2-butynyloxy group, 4-methoxymethoxy-2-butynyloxy group, 4-dimethylamino-2-butynyloxy group, 4-pyrrolidino-2-butynyloxy group, 4-piperidino-2-butynyloxy group, 4-pyrrolidino-2-butynyloxy group, 4-methylthio-2-butynyloxy group, 4-methylsulfinyl -2-butynyloxy group, 4-methylsulfonyl-2-butynyloxy group, 4-acetyloxy-2-butynyloxy group, 4-trifluoroacetyloxy-2-butynyloxy group, and 3-butynyloxy group;
C3-C6 haloalkynyloxy groups, 4,4-difluoro-2-butynyloxy group, 4-chloro-4,4-difluoro-2-butynyloxy group, 4-bromo-4,4-difluoro-2-butynyloxy group , and a 4,4,4-trifluoro-2-butynyloxy group;
RaRbN- (wherein Ra and Rb are as defined above) is an amino group, methylamino group, ethylamino group, propylamino group, isopropylamino group, (methoxymethyl)amino group, (2-methoxy ethyl)amino group, (cyanomethyl)amino group, (2-cyanoethyl)amino group, dimethylamino group, ethyl(methyl)amino group, methyl(propyl)amino group, isopropyl(methyl)amino group, (methoxymethyl)methylamino group, (2-methoxyethyl)methylamino group, (cyanomethyl)methylamino group, (2-cyanoethyl)methylamino group, diethylamino group, ethyl(propyl)amino group, ethyl(isopropyl)amino group, ethyl(methoxymethyl) amino group, ethyl(2-methoxyethyl)amino group, (cyanomethyl)ethylamino group, (2-cyanoethyl)ethylamino group, 2,2-difluoroethylamino group, 2,2,2-trifluoroethylamino group, cyclopropylamino group, (cyclopropyl)methylamino group, pyrrolidinyl group, and piperidinyl group;
Rc-L- (wherein Rc and L are as defined above), a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, a trifluoromethanesulfinyl group, and a trifluoromethanesulfonyl group;
RdC(=O)- (wherein Rd has the same definition as above) is a formyl group, an acetyl group, a methoxyacetyl group, a cyanoacetyl group, a propionyl group, a difluoroacetyl group, a trifluoroacetyl group, a 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, ethyl(methyl)aminocarbonyl group, diethylaminocarbonyl group, (methoxymethyl)methylaminocarbonyl group, (2-methoxyethyl)methylaminocarbonyl group, (cyanomethyl)methylaminocarbonyl group, (2-cyanoethyl)methyl aminocarbonyl group, 2,2-difluoroethylaminocarbonyl group, 2,2,2-trifluoroethylaminocarbonyl group, cyclopropylaminocarbonyl group, (cyclopropyl)methylaminocarbonyl group, pyrrolidinylcarbonyl group, and pyrrolidinylcarbonyl group; peridinylcarbonyl group;
and RdC(=O)O- (wherein Rd is as defined above), a formyloxy group, an acetyloxy group, a methoxyacetyloxy group, a cyanoacetyloxy group, a propionyloxy group and a difluoroacetyloxy group , trifluoroacetyloxy group, cyclopropanecarbonyloxy 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)amino carbonyloxy group, (cyanomethyl)aminocarbonyloxy group, (2-cyanoethyl)aminocarbonyloxy group, dimethylaminocarbonyloxy group, ethyl(methyl)aminocarbonyloxy group, diethylaminocarbonyloxy group, (methoxymethyl)methylaminocarbonyloxy group group, (2-methoxyethyl)methylaminocarbonyloxy group, (cyanomethyl)methylaminocarbonyloxy group, (2-cyanoethyl)methylaminocarbonyloxy group, 2,2-difluoroethylaminocarbonyloxy group, 2,2,2 -trifluoroethylaminocarbonyloxy, cyclopropylaminocarbonyloxy, cyclopropyl(methyl)aminocarbonyloxy, pyrrolidinylcarbonyloxy, and piperidinylcarbonyloxy groups.

More preferred specific examples of the substituent F include a hydroxyl group; a cyano group;
as halogen atoms, a chlorine atom, a bromine atom and an iodine atom;
Examples of C1 to C6 alkyl groups optionally substituted by substituent C include methyl group, hydroxymethyl group, methoxymethyl group, ethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 1-methoxyethyl group, a propyl group, and an isopropyl group;
a monobromomethyl group, a difluoromethyl group, and a trifluoromethyl group as the C1 to C6 haloalkyl groups;
cyclopropyl group, cyclobutyl group, and cyclopentyl group as C3-C8 cycloalkyl groups optionally substituted with substituent C;
C2-C6 alkenyl groups optionally substituted with a substituent C include a vinyl group, a 1-propenyl group, and an allyl group;
2-fluorovinyl group and 2,2-difluorovinyl group as C2-C6 haloalkenyl groups;
Ethynyl group, 1-propynyl group, and propargyl group as C2-C6 alkynyl groups optionally substituted with substituent C;
3,3-difluoro-1-propynyl group and 3,3,3-trifluoro-1-propynyl group as C2-C6 haloalkynyl groups;
Examples of C1 to C6 alkoxy groups optionally substituted by substituent C include a methoxy group, a cyanomethoxy group, a methoxymethoxy group, an ethoxy group, a 2-methoxyethoxy group, a propyloxy group, an isopropyloxy group, a butyloxy group and an isobutyl group. oxy group, sec-butyloxy group, and t-butyloxy group;
difluoromethoxy, trifluoromethoxy, 2,2-difluoroethoxy, and 2,2,2-trifluoroethoxy groups as C1-C6 haloalkoxy groups;
C3-C8 cycloalkoxy groups optionally substituted with a substituent C include a cyclopropyloxy group, a cyclobutyloxy group and a cyclopentyloxy group;
C2-C6 alkenyloxy groups optionally substituted with substituent C include vinyloxy, 1-propenyloxy, and allyloxy groups;
2-fluorovinyloxy and 2,2-difluorovinyloxy as C2-C6 haloalkenyloxy groups;
A propargyloxy group as the C3-C6 alkynyloxy group optionally substituted with a substituent C;
4,4-difluoro-2-butynyloxy group as the C3-C6 haloalkynyloxy group;
RaRbN- (wherein Ra and Rb are as defined above), an amino group, a dimethylamino group, an ethyl(methyl)amino group, and a diethylamino group;
Rc-L- (wherein Rc and L are as defined above), a methylthio group, a methanesulfinyl group, and a methanesulfonyl group;
RdC(=O)- (wherein Rd is as defined above), a formyl group, an acetyl group, a methoxyacetyl group, a cyanoacetyl group, a difluoroacetyl group, and a trifluoroacetyl group;
and RdC(=O)O- (wherein Rd is as defined above), an acetyloxy group, a methoxyacetyloxy group, a cyanoacetyloxy group, a difluoroacetyloxy group, a trifluoroacetyloxy group, a methoxy Examples include carbonyloxy, ethoxycarbonyloxy, aminocarbonyloxy, dimethylaminocarbonyloxy, ethyl(methyl)aminocarbonyloxy, and diethylaminocarbonyloxy groups.

で表される化合物または式（１－ｂ）

で表される化合物を表す。その比率は、どちらか一方が単独、あるいは任意の割合の混合物であってよく、特に限定されることはない。The wavy line part in the compound represented by Formula (1) represents E-form or Z-form. That is, formula (1-a)

A compound or formula (1-b) represented by

Represents a compound represented by The ratio is not particularly limited, and either one may be used alone or a mixture of any ratio may be used.

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

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

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

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

Obtained by arbitrarily combining the preferred ranges of R1, R2, R3, R4, R5, X, Y, substituent A, substituent B, substituent C, substituent D, substituent E and substituent F described above. The scope of all compounds shall also be described herein as the scope of compounds represented by Formula (1) of the present invention.

Next, specific compounds of the present invention have the structural formulas shown in Table 1 (P-1 to P-30: where X in the structural formulas is an oxygen atom or a sulfur atom) and Table 2. Y (Y-1 to Y-86), and Z shown in Table 3 (Z-a0001 to Z-a0140, Z-b0001 to Z-b1300, Z-c0001 to Z-c0084, Z-d0001 to Z-d0033) It is represented by a combination of

These compounds are for illustration and the invention is not limited to them.

表３中、Ｚｂで表記される部分構造は、以下に示す式（Ｚｂ）で表される。

表３中、Ｚｃで表記される部分構造は、以下に示す式（Ｚｃ）で表される。

表３中、Ｚｄで表記される部分構造は、以下の式（Ｚｄ）で表される。

In Table 3, the partial structure represented by Za is represented by formula (Za) shown below.

In Table 3, the partial structure represented by Zb is represented by formula (Zb) shown below.

In Table 3, the partial structure represented by Zc is represented by formula (Zc) shown below.

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

式中、Ｚ１はＣ１～Ｃ６のアルキル基を表し、Ｒ２２は水素原子またはＣ１～Ｃ６のアルキル基を表し、Ｒ２、ＸおよびＹは、前記と同義である。The method for producing the compound represented by formula (1) of the present invention is shown below. The production method of the compound of the present invention is not limited to production method A to production method AQ.
[Manufacturing method A]

In the formula, Z1 represents a C1-C6 alkyl group, R22 represents a hydrogen atom or a C1-C6 alkyl group, and R2, X and Y are as defined above.

Production method A is a method for producing a compound represented by formula (8), which is a production intermediate of the compound of the present invention, wherein the compound represented by formula (6) is combined with the compound represented by formula (7). , in the presence of a base and in a solvent.

The compound represented by formula (6) used in this reaction can be obtained as a commercial product, or can be produced using Reference Examples or known methods.

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

The amount of the compound represented by formula (7) used in this reaction is particularly limited as long as it is 1 equivalent or more relative to the compound represented by formula (6), as long as the desired reaction proceeds. but usually 1 equivalent or more and 3 equivalents or less.

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

The base used in this reaction is not particularly limited as long as the intended reaction proceeds, but is usually 0.01 equivalent or more and 3 equivalents or less with respect to the compound represented by formula (6). .

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

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

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

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

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

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

式中、Ｒ２２ａはＣ１～Ｃ６のアルキル基を表し、Ｒ２、Ｘ、ＹおよびＺ１は、前記と同義である。[Manufacturing method B]

In the formula, R22a represents a C1-C6 alkyl group, and R2, X, Y and Z1 are as defined above.

Production method B is a method for obtaining a production intermediate represented by formula (8b) among the compounds represented by formula (8), wherein the compound represented by formula (8a) is subjected to acidic conditions or a base It is a production method including reacting in a solvent under toxic conditions.

First, the reaction under acidic conditions will be described.
Acids used in this reaction include inorganic acids such as hydrochloric acid, hydrobromic acid and phosphoric acid, and organic acids such as acetic acid, methanesulfonic acid, p-toluenesulfonic acid and trifluoroacetic acid. There are no particular restrictions as long as the intended reaction proceeds.

The amount of acid used in this reaction may be a catalytic amount, and is not particularly limited as long as the desired reaction proceeds. Equivalent or more. Liquid acids can also be used as solvents.

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

The amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times the weight of the compound represented by the formula (8a). be.

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

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

The base used in this reaction is not particularly limited as long as it is 1 equivalent or more relative to the compound represented by formula (8a), as long as the desired reaction proceeds. equivalent or less.

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

The amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times the weight of the compound represented by the formula (8a). be.

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

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

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

The solvent can be distilled off from the reaction mixture containing the compound represented by formula (8b) obtained above under reduced pressure as long as the compound does not decompose.

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

（式中、Ｒ２、Ｘ、ＹおよびＺ１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 (8b) is represented by formula (8b')

(Wherein, R2, X, Y and Z1 are as defined above.)
Also includes isomers represented by

The compound represented by formula (8b') can be handled in the same manner as the compound represented by formula (8b), and can be applied to production method C, for example. In addition, the compound represented by formula (8b') contains an asymmetric carbon, and the isomers may be mixed alone or in an arbitrary ratio. Furthermore, a mixture of the compound represented by the formula (8b) and the compound represented by the formula (8b') may be used, and the isomers may be mixed alone or in any ratio.

式中、Ｒ２３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、Ｒ２２、Ｘ、ＹおよびＺ１は、前記と同義である。[Manufacturing method C]

In the formula, R23 is a hydrogen atom, a hydroxyl group, a cyano group, a C1-C6 alkyl group optionally substituted with a substituent A, a C1-C6 haloalkyl group optionally substituted with a substituent A, a C3- C8 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-C6 alkoxy group optionally substituted with substituent A, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group optionally substituted with substituent A, substituted 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- (wherein Ra and Rb are as defined above), and R2, R22, X, Y and Z1 are as defined above.

Production method C is a method for obtaining the compound represented by formula (9), which is a production intermediate of the compound of the present invention, and comprises reacting the compound represented by formula (8) with _R23NH2 in the presence of an acid. It is a manufacturing method including making

_R23NH2 used in this reaction can be obtained as a commercial product or produced by a known method. _R23NH2 may be a salt formed with an acidic compound such as hydrochloric acid or acetic acid, and is not particularly limited as long as the intended reaction proceeds.

_R23NH2 used in this reaction may be 1 equivalent or more relative to the compound represented by formula (8), and is not particularly limited as long as the desired reaction proceeds. It is more than 200 equivalents or less.

Examples of the acid used in this reaction include inorganic acids such as hydrochloric acid and sulfuric acid, and organic acids such as acetic acid, methanesulfonic acid and p-toluenesulfonic acid. acetic acid is preferred. Also, when using a salt of _R23NH2 with an acidic compound, the use of an acid is not essential.

The amount of the acid used in this reaction may be 1 equivalent or _more relative to R23NH2, and is not particularly limited as long as the desired reaction proceeds, but is usually 1 equivalent or more and 200 equivalents or less. . Moreover, when the acid used is liquid, it can also be used as a solvent.

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

The amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times the weight of the compound represented by the formula (8). be.

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

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

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

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

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

式中、Ｌｖはメタンスルホニル基、トリフルオロメタンスルホニル基、ｐ‐トルエンスルホニル基、ハロゲン原子等の脱離基を表し、Ｒ１、Ｒ２、Ｘ、ＹおよびＺ１は、前記と同義である。[Manufacturing method D]

In the formula, Lv represents a leaving group such as methanesulfonyl group, trifluoromethanesulfonyl group, p-toluenesulfonyl group and halogen atom, and R1, R2, X, Y and Z1 are as defined above.

Production method D is a method for obtaining a compound represented by formula (9b), which is a production intermediate of the compound of the present invention, wherein the compound represented by formula (9a) and R1-Lv are reacted in the presence of a base, It is a manufacturing method including reacting in a solvent.

The compound represented by the formula (9a), which is the raw material of the present invention, is prepared according to Production Method C and Journal of OHeterocyclic Chemistry, Vol. 20, pp. 65-67 (1983). Non-Patent Literature, etc., can be used for synthesis.

R1-Lv used in this reaction can be obtained as a commercial product or produced by a known method.
Examples of the base used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, and sodium hydride. will not be

The amount of the base used in this reaction may be 1 equivalent or more with respect to the compound represented by formula (9a), and is not particularly limited as long as the desired reaction proceeds. It is equal to or more and 10 equivalents or less.

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

The amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times the weight of the compound represented by the formula (9a). be.

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

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

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

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

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

式中、ＳＲは硫黄化剤を表し、Ｒ１、Ｒ２、ＹおよびＺ１は、前記と同義である。[Manufacturing method E]

In the formula, SR represents a sulfurizing agent, and R1, R2, Y and Z1 are as defined above.

Production method E is a method for obtaining a compound represented by formula (9b-2) among the compounds represented by formula (9b), wherein the compound represented by formula (9b-1) and a sulfurizing agent (SR) in a solvent.

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

The amount of the sulfurizing agent used in this reaction may be 0.5 equivalents or more with respect to the compound represented by formula (9b-1), and is not particularly limited as long as the intended 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, but ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane, Benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, and the like are included. These solvents can be used singly or as a mixture of two or more at any ratio.

The amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times the weight of the compound represented by formula (9b-1). It is below.

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

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

The reaction mixture containing the compound represented by formula (9b-2) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.

From the reaction mixture containing the compound represented by formula (9b-2) obtained above, the solvent can be distilled off under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (9b-2) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. with an appropriate solvent. It may be appropriately set according to the desired purity.

式中、Ｒ２ａは、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよい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、またはＲｄＣ（＝Ｏ）－（ここで、Ｒｄは、前記と同義である。）を表し、Ｒ１、Ｘ、Ｙ、Ｚ１およびＬｖは、前記と同義である。[Manufacturing method F]

In the formula, R2a is a C1-C6 alkyl group optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with a substituent A, a substituent a C2-C6 alkenyl group optionally substituted with A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group optionally substituted with a substituent A, a C2-C6 haloalkynyl group, or RdC (=O)-(wherein Rd is as defined above), and R1, X, Y, Z1 and Lv are as defined above.

In production method F, among the compounds represented by formula (9b), R2a is a C1 to C6 alkyl group optionally substituted with a substituent A, a C1 to C6 haloalkyl group optionally substituted with a substituent A, a C3-C8 cycloalkyl group optionally substituted with a substituent A, a C2-C6 alkenyl group optionally substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 optionally substituted with a substituent A A method for obtaining a compound represented by formula (9b-4), which is an alkynyl group, a C2-C6 haloalkynyl group, or RdC(=O)- (wherein Rd is as defined above). A production method comprising reacting a compound represented by formula (9b-3) with R2a-Lv in the presence of a base in a solvent.

R2a-Lv used in this reaction can be obtained as a commercial product or produced by a known method.
The amount of R2a-Lv used in this reaction may be 1 equivalent or more relative to the compound represented by formula (9b-3), and is not particularly limited as long as the desired reaction proceeds. , usually 1 equivalent or more and 1.8 equivalent or less.

Bases used in this reaction include metal hydrides such as sodium hydride, organic lithiums such as methyllithium, butyllithium, sec-butyllithium, t-butyllithium and hexyllithium, lithium diisopropylamide and hexamethyldisilazane. Metal amides such as lithium, sodium hexamethyldisilazane and potassium hexamethyldisilazane are exemplified.

The amount of the base used in this reaction may be 1 equivalent or more with respect to the compound represented by formula (9b-3), and is not particularly limited as long as the intended reaction proceeds. , 1 equivalent or more and 10 equivalents or less.

The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane, 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 singly or as a mixture of two or more at any ratio.

The amount of the solvent used in this reaction is not particularly limited as long as the intended reaction proceeds, but usually 3 to 200 times the weight of the compound represented by formula (9b-3). It is below.

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

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

The reaction mixture containing the compound represented by formula (9b-4) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.

From the reaction mixture containing the compound represented by formula (9b-4) obtained above, the solvent can be distilled off under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (9b-4) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. with an appropriate solvent. It may be appropriately set according to the desired purity.

式中、Ｏｘは酸化剤を表し、Ｒ１、Ｒ２、Ｘ、ＹおよびＺ１は、前記と同義である。[Manufacturing method G]

In the formula, Ox represents an oxidizing agent, and R1, R2, X, Y and Z1 are as defined above.

Production method G is a method for obtaining a compound represented by formula (10), which is a production intermediate of the compound of the present invention, wherein the compound represented by formula (9b) and an oxidizing agent (Ox) are reacted in a solvent. It is a manufacturing method including reacting with.

The oxidizing agent used in this reaction includes metal oxides such as manganese dioxide, benzoquinones such as 2,3-dichloro-5,6-dicyano-p-benzoquinone, azobisisobutyronitrile, benzoyl peroxide, and the like. and N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, 1,3-dichloro-5,5-dimethylhydantoin, 1,3-dibromo-5,5-dimethylhydantoin, 1,3- A combination with a halogenating agent such as diiodo-5,5-dimethylhydantoin can be used.

A method in which the oxidizing agent is a metal oxide will be described below.
The amount of the oxidizing agent used in this reaction is not particularly limited as long as it is 1 equivalent or more with respect to the compound represented by formula (9b), as long as the desired reaction proceeds. It is equal to or more and 200 equivalents or less.

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

The amount of the solvent used in this reaction is not particularly limited as long as the intended reaction proceeds, but is usually 3 to 200 times the weight of the compound represented by the formula (9b). be.

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

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

The reaction mixture containing the compound represented by formula (10) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.

From the reaction mixture containing the compound represented by formula (10) obtained above, the solvent can be distilled off under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (10) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. with an appropriate solvent. It may be appropriately set according to the desired purity.

A method in which the oxidizing agent is a benzoquinone will be described below.
The amount of the oxidizing agent used in this reaction is not particularly limited as long as it is 1 equivalent or more with respect to the compound represented by formula (9b), as long as the desired reaction proceeds. It is equal to 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 thereof include halogen-based solvents such as carbon tetrachloride. These solvents can be used singly or as a mixture of two or more at any ratio.

The amount of the solvent used in this reaction is not particularly limited as long as the intended reaction proceeds, but is usually 3 to 200 times the weight of the compound represented by the formula (9b). be.

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

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

The reaction mixture containing the compound represented by formula (10) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.

From the reaction mixture containing the compound represented by formula (10) obtained above, the solvent can be distilled off under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (10) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. with an appropriate solvent. It may be appropriately set according to the desired purity.

A method in which the oxidizing agent is a combination of a radical initiator and a halogenating agent is described below.
The amounts of the radical initiator and the halogenating agent used in this reaction are 0.01 equivalent or more and 1.0 equivalent or more, respectively, with respect to the compound represented by the formula (9b), so that the target reaction proceeds. It is not particularly limited as long as it does. Generally, the amount of the radical initiator is 0.01 to 1 equivalent, and the amount of the halogenating agent is 1 to 3 equivalents.

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

The amount of the solvent used in this reaction is not particularly limited as long as the intended reaction proceeds, but is usually 3 to 200 times the weight of the compound represented by the formula (9b). be.

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

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

The reaction mixture containing the compound represented by formula (10) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.

From the reaction mixture containing the compound represented by formula (10) obtained above, the solvent can be distilled off under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (10) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. with an appropriate solvent. It may be appropriately set according to the desired purity.

式中、Ｒ２ｂはハロゲン原子を表し、Ｚ２はＣ１～Ｃ６のアルキル基またはＲ５ＯＮ＝Ｃ（Ｒ４）－（Ｒ４およびＲ５は前記と同義であり、ＯＮ結合は単独または任意の割合の異性体を含む）を表し、ＨａｌＲはハロゲン化剤を表し、Ｒ１、ＸおよびＹは前記と同義である。[Manufacturing method H]

In the formula, R2b represents a halogen atom, Z2 is a C1-C6 alkyl group or R5ON=C(R4)-(R4 and R5 are as defined above, and the ON bond is singular or contains isomers in any proportion. ), HalR represents a halogenating agent, and R1, X and Y are as defined above.

Production method H is a method for obtaining a compound represented by formula (10b) in which R2b represents a halogen atom, wherein the compound represented by formula (10a) and a halogenating agent (HalR) are reacted in a solvent. It is a manufacturing method including making

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

The amount of the halogenating agent used in this reaction is not particularly limited as long as it is 1 equivalent or more relative to the compound represented by formula (10a) as long as the desired reaction proceeds. It is 1 equivalent or more and 10 equivalents or less. However, the amount of the hydantoin-containing halogenating agent is not particularly limited as long as it is 0.5 equivalents or more as long as the intended 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, an acid such as an inorganic acid such as hydrochloric acid or sulfuric acid, or an organic acid such as acetic acid, trifluoroacetic acid, methanesulfonic acid or trifluoromethanesulfonic acid may be added. can be done.

When the halogenating agent used in this reaction is an iodinating agent, the amount of the acid used is 0.01 equivalent or more with respect to the compound represented by the formula (10a), so that the intended reaction proceeds. Although it is not particularly limited as long as it is, 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. , diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, and other ether solvents; methanol, ethanol, isopropanol, and other alcohol solvents; benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, and other benzene solvents. , ethyl acetate, isopropyl acetate, ester solvents such as butyl acetate, nitrile solvents such as acetonitrile, N-methylpyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide and other amide solvents, 1,3- Urea-based solvents such as dimethyl-2-imidazolidinone, halogen-based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride can be used. These solvents can be used singly or as a mixture of two or more at any ratio.

The amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times the weight of the compound represented by formula (10a). be.

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

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

The reaction mixture containing the compound represented by formula (10b) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.

The solvent can be distilled off from the reaction mixture containing the compound represented by formula (10b) obtained above under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (10b) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, or the like with an appropriate solvent. It may be appropriately set according to the desired purity.

式中、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、Ｒ２ｃ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Ｃ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基を表し、Ｊが硫黄原子の場合、Ｒ２ｃ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、Ｒ２ｂ、Ｘ、ＹおよびＺ２は前記と同義である。[Manufacturing method I]

In the formula, J represents an oxygen atom or a sulfur atom, and when J is an oxygen atom, R2c is a C1 to C6 alkyl group optionally substituted with a substituent A, a C1 to C6 haloalkyl group, a substituent A optionally substituted C3-C8 cycloalkyl group optionally substituted with substituent A C2-C6 alkenyl group optionally substituted with substituent A C2-C6 haloalkenyl group optionally substituted with substituent A C2 -C6 alkynyl group, C2-C6 haloalkynyl group, when J is a sulfur atom, R2c represents a C1-C6 alkyl group or a C1-C6 haloalkyl group, Q represents a hydrogen atom or a metal, R1, R2b, X, Y and Z2 are as defined above.

In production method I, J represents an oxygen atom or a sulfur atom, and when J is an oxygen atom, R2c is a C1 to C6 alkyl group optionally substituted with a substituent A, a C1 to C6 haloalkyl group, a substituent A C3-C8 cycloalkyl group optionally substituted with A, a C2-C6 alkenyl group optionally substituted with a substituent A, a C2-C6 haloalkenyl group optionally substituted with a substituent A represents a good C2-C6 alkynyl group or a C2-C6 haloalkynyl group, and when J is a sulfur atom, R2c represents a C1-C6 alkyl group or a C1-C6 haloalkyl group represented by formula (10c) A method for obtaining a compound, which includes obtaining a compound represented by the formula (10b) by a coupling reaction in which R2c-JQ is reacted in the presence of a transition metal.

Preferred R2b in the compound represented by formula (10b) is a chlorine atom, a bromine atom, or an iodine atom.

R2c-JQ used in this reaction is commercially available or can be produced by a known method. Preferred Q is a hydrogen atom or alkali metals such as sodium and potassium.

The amount of R2c-JQ used in this reaction is not particularly limited as long as it is 1 equivalent or more relative to the compound represented by formula (10b), as long as the intended 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, palladium acetate, [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride, tris(dibenzylideneacetone) dipalladium, tetrakis ( and palladium compounds such as triphenylphosphine)palladium and bis(triphenylphosphine)palladium dichloride.

The amount of the transition metal used in this reaction is usually 0.001 equivalent or more and 1 equivalent or less with respect to the compound represented by formula (10b), but is particularly limited as long as the desired reaction proceeds. will not be

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

The amount of the phosphine ligand used in this reaction is usually 0.001 equivalent or more and 1 equivalent or less with respect to the compound represented by formula (10b), and is particularly not limited.

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.

The amount of the base used in this reaction is not particularly limited as long as it is 1 equivalent or more relative to the compound represented by formula (10b), as long as the desired reaction proceeds. 50 equivalents or less.

The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but R2c-JH (wherein R2c is as defined above and J is an oxygen atom. ), 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, etc. is mentioned. These solvents can be used singly or as a mixture of two or more at any ratio.

The amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times the weight of the compound represented by the formula (10b). be.

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

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

The reaction mixture containing the compound represented by formula (10c) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.

The solvent can be distilled off from the reaction mixture containing the compound represented by formula (10c) obtained above under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (10c) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. with an appropriate solvent. It may be appropriately set according to the desired purity.

式中、Ｒ２ｄ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、Ｒ２ｄ－Ｂは有機ボロン酸類を表し、Ｒ１、Ｒ２ｂ、Ｘ、ＹおよびＺ２は前記と同義である。[Manufacturing method J]

In the formula, R2d is a C1-C6 alkyl group optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with a substituent A, a substituent A represents a C2-C6 alkenyl group or a C2-C6 haloalkenyl group optionally substituted with, R2d-B represents an organic boronic acid, and R1, R2b, X, Y and Z2 are as defined above. .

In production method J, R2d is a C1-C6 alkyl group optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with a substituent A, substituted A method for obtaining a compound represented by formula (10d), which is a C2-C6 alkenyl group or a C2-C6 haloalkenyl group optionally substituted with group A, wherein the compound represented by formula (10b) It is a production method including obtaining by Suzuki-Miyaura coupling in which a compound and organic boronic acids (R2d-B) are reacted in the presence of transition metals and a base.

In formula (10b), preferred R2b is a chlorine atom, a bromine atom, or an iodine atom.
R2d-B used in this reaction represents an organic boronic acid such as an organic boronic acid or an organic boronate ester, and can be obtained as a commercially available product or produced by a known method.

The amount of R2d-B used in this reaction is not particularly limited as long as it is 1 equivalent or more with respect to the compound represented by formula (10b), as long as the target reaction proceeds. , 1 equivalent or more and 10 equivalents or less.

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

The amount of the transition metal used in this reaction is usually 0.001 equivalent or more and 1 equivalent or less with respect to the compound represented by formula (10b), but is particularly limited as long as the desired reaction proceeds. will not be

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

The amount of the phosphine ligand used in this reaction is usually 0.001 equivalent or more and 1 equivalent or less with respect to the compound represented by formula (10b), and is particularly not limited.

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

The amount of the base used in this reaction is not particularly limited as long as it is 1 equivalent or more relative to the compound represented by formula (10b), as long as the desired reaction proceeds. 50 equivalents or less.

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

The amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times the weight of the compound represented by the formula (10b). be.

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

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

The reaction mixture containing the compound represented by formula (10d) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.

The solvent can be distilled off from the reaction mixture containing the compound represented by formula (10d) obtained above under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (10d) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. with an appropriate solvent. It may be appropriately set according to the desired purity.

式中、Ｒ２ｅ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、Ｒ２ｂ、Ｘ、ＹおよびＺ２は前記と同義である。[Manufacturing method K]

In the formula, R2e represents a C2-C6 alkynyl group or a C2-C6 haloalkynyl group optionally substituted with a substituent A, and R1, R2b, X, Y and Z2 are as defined above.

Production method K is a method for obtaining a compound represented by formula (10e), wherein R2e is a C2-C6 alkynyl group optionally substituted with a substituent A or a C2-C6 haloalkynyl group, A production method comprising obtaining by Sonogashira coupling in which the compound represented by (10b) and a terminal alkyne compound are reacted in the presence of transition metals and a base.

In formula (10b), preferred R2b is a chlorine atom, a bromine atom, or an iodine atom.
The terminal alkyne compound used in this reaction can be obtained as a commercial product or produced by a known method. Trimethylsilylacetylene can also be used as the terminal alkyne compound. In this case, it is necessary to desilylate after introducing a trimethylsilylethynyl group into the compound represented by formula (10b). For desilylation, see Journal of the American Chemical Society, Vol. 131, No. 2, pp. 634-643 (2009). and Journal of Organometallic Chemistry, Vol. 696, No. 25, pp. 4039-4045 (2011). Non-Patent Literature, etc. can be referred to.

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

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

The amount of transition metals used in this reaction is usually 0.001 equivalents or more of palladium compounds and copper compounds, respectively, relative to the compound represented by formula (10b). There are no particular restrictions as long as it progresses. Preferred amounts for both are 0.001 equivalent or more and 1 equivalent or less.

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

The amount of the base used in this reaction is not particularly limited as long as it is 1 equivalent or more relative to the compound represented by formula (10b), as long as the desired reaction proceeds. 50 equivalents or less. In addition, organic bases in liquid form can be used as solvents.

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

The amount of the phosphine ligand used in this reaction is usually 0.001 equivalent or more and 1 equivalent or less with respect to the compound represented by formula (10b), and is particularly not limited.

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

The amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times the weight of the compound represented by the formula (10b). be.

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

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

The reaction mixture containing the compound represented by formula (10e) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.

The solvent can be distilled off from the reaction mixture containing the compound represented by formula (10e) obtained above under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (10e) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. with an appropriate solvent. It may be appropriately set according to the desired purity.

式中、Ｚ３はハロゲン原子を表し、ＨａｌＲ、Ｒ１、Ｒ２、ＸおよびＹは前記と同義である。[Manufacturing method L]

In the formula, Z3 represents a halogen atom, HalR, R1, R2, X and Y are as defined above.

Production method L is a method for obtaining a compound represented by formula (10f) in which Z3 is a halogen atom, and is represented by formula (10-1) using a radical initiator and a halogenating agent (HalR). A manufacturing method comprising reacting compounds.

In formula (10f), preferred Z3 is a chlorine atom, a bromine atom, or an iodine atom.
Radical initiators used in this reaction include azobisisobutyronitrile, benzoyl peroxide and the like.

The amount of the radical initiator used in this reaction is not particularly limited as long as the desired reaction proceeds, but usually 0.01 equivalent with respect to the compound represented by formula (10-1) It is more than 1.0 equivalent or less.

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

The amount of the halogenating agent used in this reaction is not particularly limited as long as it is 2 equivalents or more with respect to the compound represented by formula (10-1), as long as the desired reaction proceeds. Usually, it is 2 equivalents or more and 2.8 equivalents or less.

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

The amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times the weight of the compound represented by formula (10-1). It is below.

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

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

The reaction mixture containing the compound represented by formula (10f) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.

The solvent can be distilled off from the reaction mixture containing the compound represented by formula (10f) obtained above under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (10f) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. with an appropriate solvent. It may be appropriately set according to the desired purity.

式中、Ｒ１、Ｒ２、Ｘ、ＹおよびＺ３は前記と同義である。[Manufacturing method M]

In the formula, R1, R2, X, Y and Z3 are as defined above.

Production method M is a method for obtaining a compound represented by formula (10g), which is a production intermediate of the compound of the present invention, and includes hydrolyzing a compound represented by formula (10f) in the presence of water. manufacturing method.

In formula (10f), preferred Z3 is a chlorine atom, a bromine atom, or an iodine atom.
Water is essential for this reaction. In addition, silver nitrate can be used to facilitate the reaction.

The amount of water used in this reaction is not limited as long as it is 1 equivalent or more relative to the compound represented by formula (10f), as long as the desired reaction proceeds. Also, water can be used as a solvent.

The amount of silver nitrate used in this reaction is not limited as long as it is 2 equivalents or more with respect to the compound represented by formula (10f), as long as the desired reaction proceeds. equivalent or less.

The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds. nitrile-based solvents such as system solvents, acetonitrile, and the like. These solvents can be used singly or as a mixture of two or more at any ratio.

The amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times the weight of the compound represented by the formula (10f). be.

The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but it is usually from -10°C to 100°C or below the boiling point of the solvent.

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

The reaction mixture containing the compound represented by the formula (10 g) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.

The solvent can be distilled off from the reaction mixture containing the compound represented by the formula (10g) obtained above under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by the formula (10g) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. with an appropriate solvent. It may be appropriately set according to the desired purity.

式中、Ｒ４ａは置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、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。）、置換基Ｄで適宜０～５置換されてもよいフェニル基を有するＣ１～Ｃ６のアルキル基（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。）、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を有するＣ１～Ｃ６のハロアルキル基（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、Ｒ１、Ｒ２、ＸおよびＹは前記と同義である。[Manufacturing method N]

In the formula, R4a is a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with a substituent C, a substituent C C2-C6 alkenyl group optionally substituted with C2-C6 haloalkenyl group, C2-C6 alkynyl group optionally substituted with substituent C, C2-C6 haloalkynyl group, substituent D A phenyl group optionally substituted with 0 to 5 substituents (however, in the case of two or more substituents D, each is independent.), a phenyl group optionally substituted with 0 to 5 substituents D C1-C6 alkyl group (however, in the case of 2 or more substituents D, each is independent), or C1-C6 haloalkyl having a phenyl group optionally substituted with 0-5 substituents D group (however, in the case of disubstituted or more substituents D, each is independent), and R1, R2, X and Y are as defined above.

In production method N, R4a is a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with a substituent C, substituted C2-C6 alkenyl group optionally substituted by group C, C2-C6 haloalkenyl group, C2-C6 alkynyl group optionally substituted by substituent C, C2-C6 haloalkynyl group, substituted a phenyl group optionally substituted with 0 to 5 substituents D (however, in the case of disubstituted or more substituents D, each is independent), a phenyl group optionally substituted with 0 to 5 substituents D (However, in the case of two or more substituents D, each is independent.), or C1 to C6 having a phenyl group optionally substituted with a substituent D from 0 to 5 A method for obtaining a compound represented by the formula (10h) which is a haloalkyl group of (however, in the case of disubstituted or more substituents D, each is independent), the compound represented by the formula (10g) and an organometallic reagent in a solvent.

The organometallic reagent used in this reaction includes an organomagnesium halide (R4a-Mg-Hal: where Hal represents a halogen atom and R4a is as defined above.), an organolithium reagent (R4a-Li: Here, R4a is as defined above.), an organomagnesium halide-zinc(II)ate complex reagent ([(R4a) ₃ -Zn] ^- [Mg-Hal] ⁺ [Mg-(Hal) ₂ ] ₂ : Here, R4a and Hal are as defined above.) and the like. These organometallic reagents are commercially available or can be produced by known methods.

The amount of the organometallic reagent used in this reaction may be 1 equivalent or more with respect to the formula represented by formula (10g), and is not particularly limited as long as the desired reaction proceeds. Usually, it is 1 equivalent or more and 10 equivalents or less.

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

The amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times the weight of the compound represented by the formula (10 g). be.

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

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

The reaction mixture containing the compound represented by the formula (10h) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.

The solvent can be distilled off from the reaction mixture containing the compound represented by formula (10h) obtained above under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (10h) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. with an appropriate solvent. It may be appropriately set according to the desired purity.

式中、Ｏｘ’は酸化剤を表し、Ｒ１、Ｒ２、Ｘ、ＹおよびＲ４ａは前記と同義である。[Manufacturing method O]

In the formula, Ox' represents an oxidizing agent, and R1, R2, X, Y and R4a are as defined above.

Production method O is a method for obtaining a compound represented by formula (10i), which is a production intermediate of the compound of the present invention, wherein a compound represented by formula (10h) and an oxidizing agent (Ox′) are combined in a solvent It is a manufacturing method including reacting in.

This production method is carried out by an oxidation method commonly used by those skilled in the art such as Dess-Martin oxidation, Swern oxidation, Parikh-Doering oxidation, etc. can be done. Moreover, the oxidation reaction is not particularly limited as long as the intended reaction proceeds. Here we describe a method for the Palik-Daering oxidation using dimethylsulfoxide, a pyridine-sulfur trioxide complex and a base in a solvent.

Dimethyl sulfoxide used in this reaction is not particularly limited as long as it is 1 equivalent or more relative to the compound represented by formula (10h), as long as the desired reaction proceeds, and it can also be used as a solvent. can also

The pyridine-sulfur trioxide complex used in this reaction is not particularly limited as long as it is 1 equivalent or more relative to the compound represented by the formula (10h), as long as the intended reaction proceeds. It is 1 equivalent or more and 20 equivalents or less.

Examples of the base used in this reaction include organic amines such as triethylamine, tributylamine and diisopropylethylamine.

The amount of the base used in this reaction is not particularly limited as long as it is 1 equivalent or more relative to the compound represented by the formula (10h) as long as the desired reaction proceeds, and is usually 1 equivalent or more. 50 equivalents or less.

The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds. mentioned. These solvents can be used singly or as a mixture of two or more at any ratio.

The amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but it is usually 3 to 200 times the weight of the compound represented by the formula (10h). be.

The temperature for carrying out this reaction is not particularly limited as long as the desired reaction proceeds, but is usually -10° C. or higher and 150° C. or lower or the boiling point of the solvent or lower.

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

The reaction mixture containing the compound represented by formula (10i) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.

The solvent can be distilled off from the reaction mixture containing the compound represented by formula (10i) obtained above under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (10i) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. with an appropriate solvent. It may be appropriately set according to the desired purity.

式中、Ｒ４ｂは、水素原子、置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６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。）、置換基Ｄで適宜０～５置換されてもよいフェニル基を有するＣ１～Ｃ６のアルキル基（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。）、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を有するＣ１～Ｃ６のハロアルキル基（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、Ｒ１、Ｒ２、Ｒ５、ＸおよびＹは前記と同義である。[Manufacturing method P]

In the formula, R4b is a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with a substituent C , a C2-C6 alkenyl group optionally substituted with a substituent C, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group optionally substituted with a substituent C, a C2-C6 haloalkynyl group , a phenyl group optionally substituted with 0 to 5 substituents D (however, in the case of disubstituted or more substituents D, each is independent), optionally substituted with 0 to 5 substituents D a C1 to C6 alkyl group having a phenyl group (however, in the case of two or more substituents D, each is independent), or a C1 having a phenyl group optionally substituted with a substituent D with 0 to 5 substituents; represents a ∼C6 haloalkyl group (provided that, in the case of disubstituted or more substituents D, each is independent), and R1, R2, R5, X and Y are as defined above.

In the production method P, among the compounds represented by the general formula (1), R4b is a hydrogen atom, a C1 to C6 alkyl group optionally substituted with a substituent C, a C1 to C6 haloalkyl group, a substituent C a C3-C8 cycloalkyl group optionally substituted with a C2-C6 alkenyl group optionally substituted with a substituent C, a C2-C6 haloalkenyl group optionally substituted with a substituent C a C2-C6 alkynyl group, a C2-C6 haloalkynyl group, a phenyl group optionally substituted with 0 to 5 substituents D (however, in the case of two or more substituents D, each is independent); , a C1-C6 alkyl group having a phenyl group optionally substituted with 0 to 5 substituents D (however, in the case of two or more substituents D, each is independent), or with the substituent D A compound represented by formula (1a), which is a C1 to C6 haloalkyl group having a phenyl group optionally substituted with 0 to 5 substituents (provided that, in the case of disubstituted or more substituents D, each is independent); which comprises reacting a compound represented by formula (10j) with R5ONH2 in a solvent.

R5ONH2 used in this reaction can be obtained as a commercial product or produced by a known method. R5ONH2 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 bases to be 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 is no particular limitation as long as the intended reaction proceeds. The amount of the base to be used is not particularly limited as long as it is 1 equivalent or more relative to R5ONH2, as long as the intended reaction proceeds, but it is usually 1 equivalent or more and 20 equivalents or less. It is also possible to use R5ONH2 after desalting in advance by a known method.

The amount of R5ONH2 used in this reaction is not particularly limited as long as it is 1 equivalent or more relative to the compound represented by formula (10j), as long as the desired reaction proceeds. 20 equivalents or less.

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

The amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times the weight of the compound represented by the formula (10j). be.

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

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

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

The solvent can be distilled off from the reaction mixture containing the compound represented by formula (1a) obtained above under reduced pressure as long as the compound does not decompose.

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

式中、Ｒ１、Ｒ２、ＸおよびＹは前記と同義である。[Manufacturing method Q]

In the formula, R1, R2, X and Y are as defined above.

Production method Q is a method for obtaining a compound represented by formula (1d), which is a production intermediate of the present invention, and comprises reacting a compound represented by formula (1b) with a chlorinating agent in a solvent. It is a manufacturing method including.

Examples of the chlorinating agent used in this reaction include N-chlorosuccinimide and 1,3-dichloro-5,5-dimethylhydantoin.

The amount of the chlorinating agent used in this reaction is, in the case of N-chlorosuccinimide, 1 equivalent or more relative to the compound represented by formula (1b), as long as the target reaction proceeds. Although not limited, it is usually 1 equivalent or more and 20 equivalents or less. In the case of 1,3-dichloro-5,5-dimethylhydantoin, 0.5 equivalent or more relative to the compound represented by formula (1b) is not particularly limited as long as the target reaction proceeds. However, it is usually 0.5 equivalents or more and 10 equivalents or less.

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

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

The temperature for carrying out this reaction is not particularly limited as long as the desired reaction proceeds, but is usually -10° C. or higher and 150° C. or lower or the boiling point of the solvent or lower.

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

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

The solvent can be distilled off from the reaction mixture containing the compound represented by formula (1d) obtained above under reduced pressure as long as the compound does not decompose.

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

式中、Ｒ１、Ｒ２、Ｒ４ａ、ＸおよびＹは前記と同義である。[Manufacturing method R]

In the formula, R1, R2, R4a, X and Y are as defined above.

Production method R is a method for obtaining a compound represented by formula (1e) among the compounds represented by formula (1), wherein the compound represented by formula (1d) and an organometallic reagent are combined in a solvent It is a manufacturing method including reacting in.

The organometallic reagent used in this reaction includes an organomagnesium halide (R4a-Mg-Hal: where Hal represents a halogen atom and R4a is as defined above.), an organolithium reagent (R4a-Li: Here, R4a is as defined above.) and the like. These organometallic reagents are commercially available or can be produced by known methods.

The amount of the organometallic reagent used in this reaction may be 2 equivalents or more with respect to the formula represented by formula (1d), and is not particularly limited as long as the intended reaction proceeds. Usually, it is 2 equivalents or more and 10 equivalents or less.

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

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

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

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

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

The solvent can be distilled off from the reaction mixture containing the compound represented by formula (1e) obtained above under reduced pressure as long as the compound does not decompose.

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

式中、Ｒ１、Ｒ２、Ｒａ、Ｒｂ、ＸおよびＹは前記と同義である。[Manufacturing method S]

In the formula, R1, R2, Ra, Rb, X and Y are as defined above.

Production method S is a method for obtaining a compound represented by formula (1f) among the compounds represented by formula (1), wherein the compound represented by formula (1d) and RaRbNH are combined in a solvent. It is a manufacturing method including reacting.

RaRbNH used in this reaction can be obtained as a commercial product or produced by a known method. RaRbNH 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 bases to be 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 is no particular limitation as long as the intended reaction proceeds. The amount of the base to be used is not particularly limited as long as it is 1 equivalent or more relative to RaRbNH, and is not particularly limited as long as the desired reaction proceeds. It is also possible to use RaRbNH after desalting in advance by a known method.

The amount of RaRbNH used in this reaction is not particularly limited as long as it is 2 equivalents or more with respect to the compound represented by formula (1d), as long as the desired reaction proceeds. 20 equivalents or less.

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

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

The temperature for carrying out this reaction is not particularly limited as long as the desired reaction proceeds, but is usually -10° C. or higher and 150° C. or lower or the boiling point of the solvent or lower.

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

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

The solvent can be distilled off from the reaction mixture containing the compound represented by formula (1f) obtained above under reduced pressure as long as the compound does not decompose.

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

式中、Ｒ５ａは、置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、置換基Ｄで適宜０～５置換されてもよいフェニル基を有するＣ１～Ｃ６のアルキル基（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。）、置換基Ｄで適宜０～５置換されてもよいフェニル基を有するＣ１～Ｃ６のハロアルキル基（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。）、またはＲｄＣ（＝Ｏ）－（ここで、Ｒｄは、前記と同義である。）を表し、Ｒ１、Ｒ２、Ｒ４、Ｒ５ａ、Ｘ、ＹおよびＬｖは前記と同義である。[Manufacturing method T]

In the formula, R5a is a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with a substituent C, a substituent C2-C6 alkenyl group optionally substituted with C, C2-C6 haloalkenyl group, C2-C6 alkynyl group optionally substituted with substituent C, C2-C6 haloalkynyl group, substituent a C1-C6 alkyl group having a phenyl group optionally substituted by D with 0 to 5 substituents (however, in the case of disubstituted or more substituents D, each is independent); A C1 to C6 haloalkyl group having an optionally substituted phenyl group (however, in the case of disubstituted or more substituents D, each is independent), or RdC(=O)- (wherein Rd is has the same meaning as above), and R1, R2, R4, R5a, X, Y and Lv have the same meanings as above.

Production method T is a method for obtaining a compound represented by formula (1h) among the compounds represented by formula (1), wherein the compound represented by formula (1g) and R5a-Lv are combined with a base It is a manufacturing method including reacting in the presence.

R5a-Lv used in this reaction can be obtained as a commercial product or by a known method.
R5a-Lv used in this reaction may be 1 equivalent or more relative to the compound represented by formula (1g), and is not particularly limited as long as the desired reaction proceeds. It is equal to or more and 50 equivalents or less.

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

The base used in this reaction may be 1 equivalent or more relative to the compound represented by formula (1g), and is not particularly limited as long as the desired reaction proceeds. 50 equivalents or less.

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

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

The temperature for carrying out this reaction is not particularly limited as long as the desired reaction proceeds, but is usually -10° C. or higher and 150° C. or lower or the boiling point of the solvent or lower.

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

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

The solvent can be distilled off from the reaction mixture containing the compound represented by formula (1h) obtained above under reduced pressure as long as the compound does not decompose.

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

式中、Ｒ１、Ｒ２、Ｒ８、Ｒ９、Ｒ１０、Ｒ１１、ＸおよびＹは前記と同義である。[Manufacturing method U]

In the formula, R1, R2, R8, R9, R10, R11, X and Y are as defined above.

Production method U is a method for obtaining a compound represented by formula (3), and the compound represented by formula (1d) is reacted with the compound represented by formula (11) in the presence of a base in a solvent. It is a manufacturing method including

The compound represented by formula (11) used in this reaction can be obtained as a commercial product or produced by a known method.

The compound represented by formula (11) used in this reaction may be in an amount of 1 equivalent or more relative to the compound represented by formula (1d), and is not particularly limited as long as the desired reaction proceeds. However, it is usually 1 equivalent or more and 20 equivalents or less.

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

The base used in this reaction may be 1 equivalent or more relative to the compound represented by formula (1d), and is not particularly limited as long as the desired reaction proceeds, but usually 1 equivalent or more. 20 equivalents or less.

The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane, Benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene; ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate; nitrile solvents such as acetonitrile; Examples thereof include halogen-based solvent media. These solvents can be used singly or as a mixture of two or more at any ratio.

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

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

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

The reaction mixture containing the compound represented by formula (3) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.

From the reaction mixture containing the compound represented by formula (3) obtained above, the solvent can be distilled off under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (3) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, or the like with an appropriate solvent. It may be appropriately set according to the desired purity.

式中、Ｒ８ａはハロゲン原子を表し、Ｒ１、Ｒ２、Ｒ９、Ｒ１０、Ｒ１１、ＸおよびＹは前記と同義である。[Manufacturing method V]

In the formula, R8a represents a halogen atom, and R1, R2, R9, R10, R11, X and Y are as defined above.

Production method V is a method for obtaining a compound represented by formula (3b) among the compounds represented by formula (3), wherein the compound represented by formula (3a) is used as a radical initiator and a halogenating agent. is used to react in a solvent.

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

The amount of the radical initiator used in this reaction may be 0.01 equivalent or more with respect to the compound represented by formula (3a), and is not particularly limited as long as the desired reaction proceeds. is usually 0.01 equivalent or more and 1 equivalent or less.

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

The amount of the halogenating agent used in this reaction is, in the case of imides, 1 equivalent or more relative to the compound represented by formula (3a), and is particularly limited as long as the desired reaction proceeds. Usually, it is 1 equivalent or more and 3 equivalents or less. On the other hand, with respect to hydantoins, the amount may be 0.5 equivalents or more relative to the compound represented by formula (3a), and is not particularly limited as long as the intended reaction proceeds. It is 5 equivalents or more and 1.5 equivalents or less.

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

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

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

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

The reaction mixture containing the compound represented by formula (3b) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.

The solvent can be distilled off from the reaction mixture containing the compound represented by formula (3b) obtained above under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (3b) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, or the like with an appropriate solvent. It may be appropriately set according to the desired purity.

式中、Ｒ２４はＣ１～Ｃ６のアルキル基を表し、Ｒ１、Ｒ２、Ｒ８、Ｒ１０、ＸおよびＹは前記と同義である。[Manufacturing method W]

In the formula, R24 represents a C1-C6 alkyl group, and R1, R2, R8, R10, X and Y are as defined above.

Production method W is a production method for obtaining the compound represented by formula (2a) among the compounds represented by formula (2), wherein the compound represented by formula (3c) is dissolved in a solvent in the presence of an acid. It is a manufacturing method including reacting in.

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

The amount of acid used in this reaction may be a catalytic amount, and is not particularly limited as long as the desired reaction proceeds. Equivalent or more. Liquid acids can also be used as solvents.

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

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

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

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

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

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

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

式中、Ｒ１、Ｒ２、Ｒ６、Ｒ７、ＸおよびＹは前記と同義である。[Manufacturing method X]

In the formula, R1, R2, R6, R7, X and Y are as defined above.

Production method X is a method for obtaining a compound represented by formula (2), and reacting a compound represented by formula (1d) with a compound represented by formula (12) in the presence of a base in a solvent. It is a manufacturing method including

The compound represented by formula (12) used in this reaction can be obtained as a commercial product or produced by a known method.

The compound represented by formula (12) used in this reaction may be in an amount of 1 equivalent or more relative to the compound represented by formula (1d), and is not particularly limited as long as the desired reaction proceeds. However, it is usually 1 equivalent or more and 100 equivalents or less.

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

The base used in this reaction may be 1 equivalent or more relative to the compound represented by formula (1d), and is not particularly limited as long as the desired reaction proceeds, but usually 1 equivalent or more. 20 equivalents or less.

The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane, Benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene; ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate; nitrile solvents such as acetonitrile; Examples thereof include halogen-based solvent media. These solvents can be used singly or as a mixture of two or more at any ratio.

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

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

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

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

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

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

式中、Ｒ６ａはハロゲン原子を表し、Ｒ１、Ｒ２、Ｒ７、ＸおよびＹは前記と同義である。[Manufacturing method Y]

In the formula, R6a represents a halogen atom, and R1, R2, R7, X and Y are as defined above.

Production method Y is a method for obtaining a compound represented by formula (2c) among compounds represented by formula (2), wherein a compound represented by formula (2b) and a halogenating agent are It is a manufacturing method including reacting in.

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

The amount of the halogenating agent used in this reaction is not particularly limited as long as it is 1 equivalent or more with respect to the compound represented by formula (2b), as long as the intended reaction proceeds. It is 1 equivalent or more and 100 equivalents or less. However, the amount of the hydantoin-containing halogenating agent is not particularly limited as long as it is 0.5 equivalents or more as long as the intended 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, an acid such as an inorganic acid such as hydrochloric acid or sulfuric acid, or an organic acid such as acetic acid, trifluoroacetic acid, methanesulfonic acid or trifluoromethanesulfonic acid may be added. can be done.

When the halogenating agent used in this reaction is an iodinating agent, the amount of the acid used is 0.01 equivalent or more with respect to the compound represented by the formula (2b), so that the intended reaction proceeds. Although it is not particularly limited as long as it is, 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. , diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, and other ether solvents; methanol, ethanol, isopropanol, and other alcohol solvents; benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, and other benzene solvents. , ethyl acetate, isopropyl acetate, ester solvents such as butyl acetate, nitrile solvents such as acetonitrile, N-methylpyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide and other amide solvents, 1,3- Urea-based solvents such as dimethyl-2-imidazolidinone, halogen-based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride can be used. These solvents can be used singly or as a mixture of two or more at any ratio.

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

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

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

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

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

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

式中、Ｒ１、Ｒ２、Ｒ６、Ｒｉ、Ｒｊ、Ｒｋ、ＸおよびＹは前記と同義である。[Manufacturing method Z]

In the formula, R1, R2, R6, Ri, Rj, Rk, X and Y are as defined above.

Production method Z is a method for obtaining a compound represented by formula (2e) among compounds represented by formula (2), wherein a compound represented by formula (2d) and a fluorine-containing compound are It is a manufacturing method including reacting in.

Examples of the fluorine-containing compound used in this reaction include inorganic salts such as sodium fluoride, potassium fluoride and cesium fluoride, and organic salts such as tetrabutylammonium fluoride.

The amount of the fluorine-containing 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 (2d) as long as the desired reaction proceeds. , 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, but ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane, alcohol solvents such as methanol, ethanol and isopropanol; benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene; ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate; nitrile solvents such as acetonitrile; Halogen-based solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride are included. These solvents can be used singly or as a mixture of two or more at any ratio.

The amount of the solvent used in this reaction is not particularly limited as long as the intended reaction proceeds, but it is usually 3 to 200 times the weight of the compound represented by the 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 from -20°C to 150°C or below the boiling point of the solvent.

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

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

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

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

式中、Ｒ４ｃおよびＲ５ｂは、それぞれ独立していて、水素原子またはＣ１～Ｃ６のアルキル基を表し、Ｒ１、Ｒ２、ＸおよびＹは前記と同義である。[Manufacturing method AA]

In the formula, R4c and R5b each independently represent a hydrogen atom or a C1-C6 alkyl group, and R1, R2, X and Y are as defined above.

Production method AA is a method for obtaining a compound represented by formula (2f) among compounds represented by formula (2), wherein the compound represented by formula (1i) is treated with iodine and It is a manufacturing method including reacting with a metal iodide in a solvent.

The compound represented by formula (1i) used in this reaction can be prepared by the method described in Production method R.

The base used in this reaction includes inorganic bases such as sodium carbonate, sodium hydrogen carbonate, potassium carbonate, potassium hydrogen carbonate, cesium carbonate, cesium hydrogen carbonate, sodium methoxide, sodium ethoxide, sodium t-butoxide, potassium t - metal alkoxides such as butoxide;

The amount of the base used in this reaction is not particularly limited as long as it is 1 equivalent or more with respect to the compound represented by formula (1i), as long as the desired reaction proceeds. It is equal to or more and 30 equivalents or less.

The amount of iodine used in this reaction is not particularly limited as long as it is 1 equivalent or more with respect to the compound represented by formula (1i), as long as the desired reaction proceeds. It is equal to or more and 30 equivalents or less.

Examples of metal iodides used in this reaction include sodium iodide and potassium iodide.

The amount of the metal iodide used in this reaction is not particularly limited as long as it is 1 equivalent or more with respect to the compound represented by formula (1i), as long as the target reaction proceeds, but preferably , 1 equivalent or more and 30 equivalents or less.

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, and dichlorobenzene; nitrile solvents such as acetonitrile; amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, and N,N-dimethylacetamide. Solvents include urea solvents such as 1,3-dimethyl-2-imidazolidinone, and halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride. These solvents can be used singly or as a mixture of two or more at any ratio.

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

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

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

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

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

式中、Ｒ６ｂは水素原子または置換基Ｅを表し、Ｏｘ’’は酸化剤を表し、Ｒ１、Ｒ２、Ｒｈ、ＸおよびＹは前記と同義である。[Manufacturing method AB]

In the formula, R6b represents a hydrogen atom or a substituent E, Ox'' represents an oxidizing agent, and R1, R2, Rh, X and Y are as defined above.

Production method AB is a method for obtaining a compound represented by formula (2h) among the compounds represented by formula (2), comprising a compound represented by formula (2g) and an oxidizing agent (Ox'') and in a solvent.

This production method is carried out by an oxidation method commonly used by those skilled in the art such as Dess-Martin oxidation, Swern oxidation, Parikh-Doering oxidation, etc. can be done. Moreover, the oxidation reaction is not particularly limited as long as the intended reaction proceeds. Here, a method for Dess-Martin oxidation using a Dess-Martin reagent in a solvent is described.

The oxidizing agent used in this reaction is Dess-Martin reagent (1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one), which is commercially available. can be obtained as

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

The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds. mentioned. These solvents can be used singly or as a mixture of two or more at any ratio.

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

The temperature for carrying out this reaction is not particularly limited as long as the desired reaction proceeds, but is usually -10° C. or higher and 150° C. or lower or the boiling point of the solvent or lower.

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

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

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

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

式中、Ｒ１、Ｒ２、Ｒ６ｂ、ＸおよびＹは前記と同義である。[Manufacturing method AC]

In the formula, R1, R2, R6b, X and Y are as defined above.

Production method AC is a method for obtaining a compound represented by formula (2j) among the compounds represented by formula (2), wherein the compound represented by formula (2i) and a fluorinating agent (FR) are in a solvent.

Fluorinating agents used in this reaction include (diethylamino)sulfur trifluoride, bis(2-methoxyethyl)aminosulfur trifluoride, N,N-diethyl-1,1,2,3,3,3-hexafluoropropyl amine, 2,2-difluoro-1,3-dimethylimidazolidine and the like.

The amount of the fluorinating agent used in this reaction may be 1 equivalent or more with respect to the compound represented by formula (2i), and is not particularly limited as long as the intended reaction proceeds. , 1 equivalent or more and 10 equivalents or less.

The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane, Benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene; nitrile solvents such as acetonitrile; halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride; Examples thereof include hydrocarbon solvents. These solvents can be used singly or as a mixture of two or more at any ratio.

The amount of the solvent used in this reaction is not particularly limited as long as the intended reaction proceeds, but is usually 3 to 200 times the weight of the compound represented by formula (2i). be.

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

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

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

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

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

式中、Ｒ１、Ｒ２、Ｒ６ｂ、Ｒｈ、Ｒｇ、ＸおよびＹは前記と同義である。[Manufacturing method AD]

In the formula, R1, R2, R6b, Rh, Rg, X and Y are as defined above.

Production method AD is a method for obtaining a compound represented by formula (2k) among the compounds represented by formula (2), wherein the compound represented by formula (2g) and RgONH2 are mixed in a solvent. It is a manufacturing method including reacting.

Carrying out production method AD according to production method P by using the compound represented by formula (10j) and R5ONH2 in production method P in place of the compound represented by formula (2g) and RgONH2, respectively. can be done.

式中、Ｒｌは水素原子またはＣ１～Ｃ４のアルキル基であり、Ｒ１、Ｒ２、Ｒ６ｂ、ＸおよびＹは前記と同義である。
Ｃ１～Ｃ４のアルキル基とは、前記したＣ１～Ｃ６のアルキル基のうち、炭素原子数が１～４個のものを表す。[Manufacturing method AE]

In the formula, Rl is a hydrogen atom or a C1-C4 alkyl group, and R1, R2, R6b, X and Y are as defined above.
The C1-C4 alkyl group means those having 1-4 carbon atoms among the above-mentioned C1-C6 alkyl groups.

Production method AE is a method for obtaining a compound represented by formula (2m) among compounds represented by formula (2), wherein a compound represented by formula (2l) and a diazophosphonate reagent are reacted with a base It is a production method in which the reaction is carried out in the presence of a solvent.

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 may be 1 equivalent or more relative to the compound represented by formula (2l), and is not particularly limited as long as the intended reaction proceeds. Usually, it is 1 equivalent or more and 10 equivalents or less.

The base used in this reaction includes 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- and metal alkoxides such as butoxide.

The amount of the base used in this reaction may be 1 equivalent or more with respect to the compound represented by formula (2l), and is not particularly limited as long as the desired reaction proceeds. It is equal to or more and 20 equivalents or less.

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

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

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

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

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

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

式中、Ｒ６ｃは、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、またはＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）を表し、
Ｒ７ａは、置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ｃで適宜置換されてもよいＣ２～Ｃ６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を表し、Ｒ１、Ｒ２、ＸおよびＹは前記と同義である。[Manufacturing method AF]

In the formula, R6c is a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 halo an alkoxy group, a C3-C8 cycloalkoxy group, or RaRbN— (wherein Ra and Rb are as defined above),
R7a is a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with a substituent C, a substituent C optionally represents an optionally substituted C2-C6 alkenyl group, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group optionally substituted with a substituent C, a C2-C6 haloalkynyl group, R1, R2, X and Y are as defined above.

Production method AF is a method for obtaining a compound represented by formula (2n) among the compounds represented by formula (2), wherein the compound represented by formula (1d) and the compound represented by formula (13) compound in the presence of a base in a solvent.

The compound represented by formula (13) used in this reaction can be obtained as a commercial product or produced by a known method.

Production method AF can be carried out according to production method X by using the compound represented by formula (12) in production method X instead of the compound represented by formula (13).

式中、Ｒ１、Ｒ２、Ｒ６ｂ、Ｒｈ、ＸおよびＹは前記と同義である。[Manufacturing method AG]

In the formula, R1, R2, R6b, Rh, X and Y are as defined above.

Production method AG is a method for obtaining formula (2g) among the compounds represented by formula (2), comprising reacting the compound represented by formula (2h) with a hydride reagent in a solvent. It is a manufacturing method including.

Examples of hydride reagents used in this reaction include boron compounds such as sodium borohydride.

The hydride reagent used in this reaction is not particularly limited as long as it is 1 equivalent or more in terms of hydride with respect to the compound represented by the formula (2h) as long as the desired reaction proceeds. , 1 equivalent or more and 40 equivalents or less.

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

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

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

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

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

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

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

式中、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、Ｒ６ｂ、ＸおよびＹは前記と同義である。
Ｃ１～Ｃ４のアルキル基とは、前記したＣ１～Ｃ６のアルキル基のうち、炭素原子数が１～４個のものを表す。[Manufacturing method AH]

In the formula, Rm and Rn each independently represent a hydrogen atom or a C1-C4 alkyl group (where the total number of carbon atoms of Rm and Rn is 4 or less), and R1, R2, R6b , X and Y are as defined above.
The C1-C4 alkyl group means those having 1-4 carbon atoms among the above-mentioned C1-C6 alkyl groups.

Production method AH is a method for obtaining a compound represented by formula (2p) among compounds represented by formula (2), wherein a compound represented by formula (2o) is reacted in a solvent in the presence of an acid. It is a manufacturing method including reacting with.

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

The amount of acid used in this reaction may be a catalytic amount, and is not particularly limited as long as the desired reaction proceeds. Equivalent or more. Liquid acids can also be used as solvents.

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

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

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

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

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

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

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

式中、Ｒ１、Ｒ２、Ｒ１２、Ｒ１３、Ｒ１４、Ｒ１５、Ｒｉ、Ｒｊ、Ｒｋ、ＸおよびＹは前記と同義である。[Manufacturing method AI]

In the formula, R1, R2, R12, R13, R14, R15, Ri, Rj, Rk, X and Y are as defined above.

Production method AI is a method for obtaining a compound represented by formula (4), wherein a compound represented by formula (1d), a compound represented by formula (14), and a fluorine-containing compound are mixed in a solvent. It is a manufacturing method including reacting.

The compound represented by formula (14) used in this reaction can be obtained as a commercial product or produced by a known method.

The amount of the compound represented by formula (14) used in this reaction is particularly limited as long as it is 1 equivalent or more relative to the compound represented by formula (1d), as long as the desired reaction proceeds. However, it is usually 1 equivalent or more and 30 equivalents or less.

Examples of the fluorine-containing compound used in this reaction include inorganic salts such as sodium fluoride, potassium fluoride and cesium fluoride, and organic salts such as tetrabutylammonium fluoride.

The amount of the fluorine-containing compound used in this reaction is not particularly limited as long as it is 2 equivalents or more with respect to the compound represented by formula (1d) as long as the desired reaction proceeds. , 2 equivalents or more and 30 equivalents or less.

The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane, Benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene; ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate; nitrile solvents such as acetonitrile; Examples include halogen-based solvents. These solvents can be used singly or as a mixture of two or more at any ratio.

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

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

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

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

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

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

式中、Ｒ３ａはハロゲン原子を表し、Ｒ３ｂは置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニルオキシ基、Ｃ２～Ｃ６のハロアルケニルオキシ基、置換基Ｃで適宜置換されてもよいＣ３～Ｃ６のアルキニルオキシ基、またはＣ３～Ｃ６のハロアルキニルオキシ基を表し、Ｙ１は、Ｒ３で適宜ｎＡ置換されてもよいＲ３ａを有するフェニル基、またはＲ３で適宜ｎＡ置換されてもよいＲ３ａを有するピリジル基を表し、Ｙ１がフェニル基の場合、ｎＡは０から４の整数を表し（ただし、２置換以上のＲ３の場合、それぞれ独立している。）、Ｙ１がピリジル基の場合、ｎＡは０～３の整数（ただし、２置換以上のＲ３の場合、それぞれ独立している。）を表し、Ｒ１、Ｒ２、Ｒ３、Ｒ４、Ｒ５、ＱおよびＸは前記と同義である。[Manufacturing method AJ]

In the formula, R3a represents a halogen atom, R3b is a C1-C6 alkoxy group optionally substituted with a substituent C, a C1-C6 haloalkoxy group, a C3-C8 optionally substituted with a substituent C a cycloalkoxy group, a C2 to C6 alkenyloxy group optionally substituted with a substituent C, a C2 to C6 haloalkenyloxy group, a C3 to C6 alkynyloxy group optionally substituted with a substituent C, or a C3 to C6 haloalkynyloxy group, Y1 represents a phenyl group having R3a optionally substituted with nA by R3, or a pyridyl group having R3a optionally substituted with nA by R3, and Y1 is In the case of a phenyl group, nA represents an integer of 0 to 4 (however, in the case of disubstituted or more R3, each is independent.), and when Y1 is a pyridyl group, nA is an integer of 0 to 3 (however, In the case of two or more substituted R3, each is independent.), and R1, R2, R3, R4, R5, Q and X are as defined above.

In production method AJ, among the compounds represented by formula (1), R3b is a C1 to C6 alkoxy group optionally substituted with a substituent C, a C1 to C6 haloalkoxy group, or a substituent C, as appropriate C3-C8 cycloalkoxy group optionally substituted, C2-C6 alkenyloxy group optionally substituted with substituent C, C2-C6 haloalkenyloxy group optionally substituted with substituent C represents a C3-C6 alkynyloxy group or a C3-C6 haloalkynyloxy group, Y1 is a phenyl group having R3a optionally substituted nA with R3, or R3a optionally substituted nA with R3; represents a pyridyl group having, when Y1 is a phenyl group, nA represents an integer of 0 to 4 (however, in the case of disubstituted or more R3, each is independent), when Y1 is a pyridyl group, nA is A method for obtaining a compound represented by the formula (1j) representing an integer of 0 to 3 (provided that each R3 is disubstituted or more is independent), the compound represented by the formula (1j) and R3b-Q in a solvent.

R3b-Q used in this reaction is commercially available or can be produced by a known method. Preferred Q is a hydrogen atom or alkali metals such as sodium and potassium.

The amount of R3b-Q used in this reaction is not particularly limited as long as it is 1 equivalent or more with respect to the compound represented by formula (1j), as long as the target reaction proceeds. , 1 equivalent or more and 30 equivalents or less. Moreover, when Q represents a hydrogen atom, it can be used as a solvent.

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

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

The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but alcoholic solvents represented by R3b-H, diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxy Ether solvents such as ethane, tetrahydrofuran and dioxane; Benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene; Ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate; Nitrile solvents such as acetonitrile; Amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide and N,N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, dichloromethane, dichloroethane, chloroform, carbon tetrachloride halogen-based solvents such as dimethylsulfoxide, sulfur-based solvents such as sulfolane, ketone-based solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and the like. These solvents can be used singly or as a mixture of two or more at any ratio.

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

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

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

The solvent can be distilled off from the reaction mixture containing the compound represented by formula (1k) obtained above under reduced pressure as long as the compound does not decompose.

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

式中、Ｒ３ｃはＣ１～Ｃ６のアルコキシ基を表し、Ｒ１、Ｒ２、Ｒ３、Ｒ４、Ｒ５、ｎＡ、ＸおよびＹ１は前記と同義である。[Manufacturing method AK]

In the formula, R3c represents a C1-C6 alkoxy group, and R1, R2, R3, R4, R5, nA, X and Y1 are as defined above.

The production method Z is a method for obtaining a compound represented by the formula (1m) having a hydroxyl group among the compounds represented by the formula (1) by reacting the compound represented by the formula (1l) with an acid. It is a manufacturing method comprising obtaining by causing

Examples of the acid used in this reaction include boron halides such as boron trichloride and boron tribromide.

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

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

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

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

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

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

The solvent can be distilled off from the reaction mixture containing the compound represented by formula (1m) obtained above under reduced pressure as long as the compound does not decompose.

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

式中、Ｒ３ｄは、置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ３～Ｃ６のハロアルキニル基、またはＲｄＣ（＝Ｏ）－（ここで、Ｒｄは、前記と同義である。）を表し、Ｒ１、Ｒ２、Ｒ３、Ｒ４、Ｒ５、ｎＡ、Ｌｖ、ＸおよびＹ１は前記と同義である。[Manufacturing method AL]

In the formula, R3d is a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with a substituent C, a substituent a C2-C6 alkenyl group optionally substituted with C, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group optionally substituted with a substituent C, a C3-C6 haloalkynyl group, or RdC (=O)-(wherein Rd is as defined above), and R1, R2, R3, R4, R5, nA, Lv, X and Y1 are as defined above.

In production method AL, among the compounds represented by formula (1), R3d is a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group optionally substituted with a substituent C, a C3-C8 cycloalkyl group optionally substituted with a substituent C, a C2-C6 alkenyl group optionally substituted with a substituent C, a C2-C6 haloalkenyl group, a C2-C6 optionally substituted with a substituent C A method for obtaining a compound represented by formula (1n) which is an alkynyl group, a C3-C6 haloalkynyl group, or RdC(=O)- (wherein Rd is as defined above), A production method comprising reacting a compound represented by formula (1m) with R3d-Lv in the presence of a base in a solvent.

R3d-Lv used in this reaction is commercially available or can be produced by a known method.

R3d-Lv used in this reaction may be 1 equivalent or more relative to the compound represented by formula (1m), and is not particularly limited as long as the desired reaction proceeds. It is equal to or more and 10 equivalents or less.

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

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

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

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

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

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

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

The solvent can be distilled off from the reaction mixture containing the compound represented by formula (1n) obtained above under reduced pressure as long as the compound does not decompose.

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

式中、Ｒ３ｅは置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、またはＣ２～Ｃ６のハロアルケニル基を表し、Ｒ３ｅ－Ｂは有機ボロン酸類を表し、Ｒ１、Ｒ２、Ｒ３、Ｒ３ａ、Ｒ４、Ｒ５、ｎＡ、ＸおよびＹ１は前記と同義である。[Manufacturing method AM]

In the formula, R3e is a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with a substituent C, a substituent C represents a C2-C6 alkenyl group or a C2-C6 haloalkenyl group optionally substituted with, R3e-B represents organic boronic acids, R1, R2, R3, R3a, R4, R5, nA, X and Y1 are as defined above.

In the production method AM, among the compounds represented by the formula (1), R3e is a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group optionally substituted with a substituent C, a C3-C8 cycloalkyl group optionally substituted with a substituent C, a C2-C6 alkenyl group optionally substituted with a substituent C, or a C2-C6 haloalkenyl group. A production method comprising obtaining by Suzuki-Miyaura coupling in which the compound represented by formula (1j) and organic boronic acids (R3e-B) are reacted in the presence of transition metals and a base.

In formula (1j), preferred R3a is a chlorine atom, a bromine atom, or an iodine atom.

R3e-B used in this reaction represents an organic boronic acid such as an organic boronic acid or an organic boronate ester, and can be obtained as a commercially available product or produced by a known method.

A production method according to production method J by using the compound represented by formula (10b) and R2d-B in production method J in place of the compound represented by formula (1j) and R3e-B, respectively AM can be performed.

式中、Ｒ３ｆは置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、またはＣ２～Ｃ６のハロアルキニル基を表し、Ｒ１、Ｒ２、Ｒ３、Ｒ３ａ、Ｒ４、Ｒ５、ｎＡ、ＸおよびＹ１は前記と同義である。[Manufacturing method AN]

In the formula, R3f represents a C2-C6 alkynyl group optionally substituted with a substituent C or a C2-C6 haloalkynyl group, and R1, R2, R3, R3a, R4, R5, nA, X and Y1 has the same meaning as above.

In the production method AN, among the compounds represented by the formula (1), R3f is a C2-C6 alkynyl group or a C2-C6 haloalkynyl group optionally substituted with a substituent C, the formula (1p) A method for obtaining a compound represented by (1j) by Sonogashira coupling in which the compound represented by (1j) is reacted with a terminal alkyne compound in the presence of a transition metal and a base. .

In formula (1j), preferred R3a is a chlorine atom, a bromine atom, or an iodine atom.

The terminal alkyne compound used in this reaction can be obtained as a commercial product or produced by a known method. Trimethylsilylacetylene can also be used as the terminal alkyne compound.

Production method AN can be carried out according to production method K by using the compound represented by formula (10b) in production method K instead of the compound represented by formula (1j).

式中、Ｒ７ｂは、置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルキル基を表し、Ｒ１、Ｒ２、ＸおよびＹは前記と同義である。[Manufacturing method AO]

In the formula, R7b represents a C1-C6 alkyl group optionally substituted with a substituent C, and R1, R2, X and Y are as defined above.

The production method AO is a method for obtaining a compound represented by the formula (2q), in which the compound represented by the formula (1d) is reacted with the compound represented by the formula (15) in the presence of a base in a solvent. It is a manufacturing method including

The compound represented by formula (15) used in this reaction can be obtained as a commercial product or produced by a known method.

The compound represented by formula (15) used in this reaction may be in an amount of 1 equivalent or more relative to the compound represented by formula (1d), and is not particularly limited as long as the desired reaction proceeds. However, it is usually 1 equivalent or more and 20 equivalents or less.

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

The base used in this reaction may be 1 equivalent or more relative to the compound represented by formula (1d), and is not particularly limited as long as the desired reaction proceeds, but usually 1 equivalent or more. 20 equivalents or less.

The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane, Benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene; ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate; nitrile solvents such as acetonitrile; Examples thereof include halogen-based solvent media. These solvents can be used singly or as a mixture of two or more at any ratio.

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

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

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

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

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

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

式中、Ｒ１、Ｒ２、Ｒ１６、Ｒ１７、Ｒ１８、Ｒ１９、Ｒ２０、Ｒ２１、Ｌｖ、ＸおよびＹは前記と同義である。[Manufacturing method AP]

In the formula, R1, R2, R16, R17, R18, R19, R20, R21, Lv, X and Y are as defined above.

Production method AP is a method for obtaining a compound represented by formula (5), and is a production method including reacting a compound represented by formula (1c) in the presence of a base in a solvent.

The compound represented by formula (1c) can be obtained by referring to production method R and the like.

The base used in this reaction is exemplified by inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate, and sodium hydride, but is not particularly limited as long as the target reaction proceeds.

The base used in this reaction may be 1 equivalent or more relative to the compound represented by formula (1c), and is not particularly limited as long as the desired reaction proceeds. 20 equivalents or less.

The solvent used in this reaction is not particularly limited as long as the intended reaction proceeds, but alcohol solvents such as tertiary butanol, diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, Ether solvents such as tetrahydrofuran and dioxane; Benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene; Nitrile solvents such as acetonitrile; Examples thereof include amide solvents such as dimethylacetamide and urea solvents such as 1,3-dimethyl-2-imidazolidinone. These solvents can be used singly or as a mixture of two or more at any ratio.

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

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

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

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

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

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

式中、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 AQ]

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

Production method AQ is a method for obtaining a compound represented by formula (Lb), wherein Lb contained in R1, _R2 , R3, R4 and R5 in the compound represented by formula (1) is SO or SO2. A compound represented by the formula (La) in which La contained in R1, R2, R3, R4 and R5 in the compound represented by the formula (1) is S, and an oxidizing agent (Ox''') , a manufacturing method including reacting in a solvent.

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

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

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

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

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

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

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

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

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

The compound represented by the formula (1) can be produced by any combination of the production methods A to AQ shown above. Alternatively, the compound represented by formula (1) can be produced by any combination of known methods and production methods A to AQ.

Since the compound of the present invention can control organisms harmful to plants, it can be used as an agricultural chemical, especially an agricultural and horticultural pest control agent. Specific examples include fungicides, insecticides, herbicides, plant growth regulators and the like. Preferably, it is a disinfectant.

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

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

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

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

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

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

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

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

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

Application of a composition (agricultural and horticultural pest control agent, agricultural and horticultural fungicide) containing the compound of the present invention is described below.

A method of applying the composition containing the compound of the present invention includes a method of contacting with plants or seeds, or a method of including in cultivation soil and contacting roots or rhizomes of plants. Specific examples include foliage spraying treatment, injection treatment, seedling box treatment, cell tray treatment, spraying treatment on plant seeds, smearing treatment on plant seeds, immersion treatment on plant seeds, and plant seeds. Dressing 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, after soil irrigation treatment Soil admixture and the like are included. Generally, any method of application as utilized by those skilled in the art will suffice.

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

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

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

The compound of the present invention may optionally be used with other pesticides such as fungicides, insecticides (including acaricides and nematicides), herbicides, microbial agents, and plant growth regulators. It can be used by mixing with a disease control agent (International Publication No. 2014/062775), a soil conditioner, a fertilizing substance, or the like as an active ingredient. The method of using the compound of the present invention and other pesticides in combination includes the method of formulating the compound of the present invention and other pesticides into one dosage form and using them, and the method of formulating the compounds of the present invention and other pesticides into separate dosage forms. method of mixing before use, method of using both formulated in separate dosage forms at the same time, or both formulated in separate dosage forms, use either one and then use the other.

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

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

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

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

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

b-5: quinone internal inhibitor (QiI agent)
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 oxidative phosphorylation uncoupling inhibitors, [b-6.1] binapacryl, [b-6.2] meptyldinocap, [ b-6.3] dinocap, [b-6.4] fluazinam and the like.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

b-23: Other fungicides Other fungicides include [b-23.1] dichlobentiazox, [b-23.2] fenpicoxamide, [b-23.3 ] dipymetitrone, [b-23.4] bupirimate, [b-23.5] dimethirimol, [b-23.6] ethirimol, [b-23.7] acetic acid triphenyltin acetate, [b-23.8]triphenyltin chloride, [b-23.9]fentin hydroxide, [b-23.10]oxolinic acid (oxolinic acid), [b-23.11] hymexazol, [b-23.12] octhilinone, [b-23.13] fosetyl, [b-23.14] phosphorus phosphorous acid, [b-23.15] sodium phosphite, [b-23.16] ammonium phosphite, [b-23.17] potassium phosphate, [b-23.18] tecloftalam, [b-23.19] triazoxide, [b-23.20] flusulfamide, [b-23 .21] diclomezine, [b-23.22] silthiofam, [b-23.23] diflumetrim, [b-23.24] methasulfocarb, [b-23 .25] cyflufenamide, [b-23.26] metrafenone, [b-23.27] pyriofenone, [b-23.28] dodine, [b-23.29 ] flutianil, [b-23.30] ferimzone, [b-23.31] oxathiapiprolin, [b-23.32] tebufloquin, [b-23.33] picarbutrazox, [b-23.34] validamycins, [b-23.35] cymoxanil ), [b-23.36] quinofumelin,

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] Expression (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] Expression (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)

[Wherein, A3 represents a hydrogen atom, a halogen atom, a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, or a cyano group; A4 represents a hydrogen atom, a C1 to C6 alkyl group, a C1 to C6 It represents a haloalkyl group or a C3-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、国際特許第０９／１３７６５１号参照）、[b-23.53] Expression (s17)

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

［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)

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

［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)

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

［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)

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

［式中、Ａ２３およびＡ２４は、それぞれ独立していて、水素原子、ハロゲン原子、Ｃ１～Ｃ６のアルキル基、またはＣ３～Ｃ８のシクロアルキル基を表し、Ｘは、酸素原子または硫黄原子を表す。］で表される化合物（国際公開第０７／０８７９０６号、国際特許第０９／０１６２２０号、国際特許第１０／１３０７６７号参照）、[b-23.57] formula (s21)

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

［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-C8 cycloalkyl group, and when m3 is 2 or more, two or more A25 represent independent substituents and may be the same or different. ] (see WO 13/092224),

［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)

[Wherein, m4 represents an integer of 0 to 5, A27 represents a C1 to C6 alkyl group, A28 represents a halogen atom, a cyano group, a C1 to C6 alkyl group, or a C1 to C6 haloalkyl group When m4 is 2 or more, 2 or more A28 each represent an independent substituent, which may be the same or different, and A29 is a C1 to C6 alkyl group, a C2 to C6 alkenyl group, or a C3 represents 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)

[Wherein, m5 represents an integer of 0 to 5, A30 represents a C1 to C6 alkyl group, A31 represents a halogen atom, a cyano group, a C1 to C6 alkyl group, or a C1 to C6 haloalkyl group When m5 is 2 or more, 2 or more A31 each represent an independent substituent, which may be the same or different, and A32 is a C1 to C6 alkyl group, a C2 to C6 alkenyl group, or a C3 represents 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、国際特許第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. ] (see International Publication No. 06/031631, International Patent No. 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-C6 alkyl group or a C1-C6 haloalkyl group, and A39 and A40 each independently represent a hydrogen atom or a halogen atom. ] (see WO 14/043376),

［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 hydrogen sulfur group (-SH), a thiocyanate group (-SCN), or a C1-C6 alkylthio group, and A42, A43, A44 and A45 are each independently , a hydrogen atom, or a halogen atom. ] (see WO 09/077443),

［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) and the like.

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

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

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

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

c-4: Sodium channel modulators Sodium channel modulators include [c-4.1] acrinathrin, [c-4.2] allethrin [(1R)-isomer] (allethrin [(1R)-isomer]), [c-4.3] bifenthrin, [c-4.4] bioallethrin, [c-4.5] bioallethrin S-cyclopentenyl isomer, [c- 4.6] bioresmethrin, [c-4.7] cycloprothrin, [c-4.8] cyfluthrin, [c-4.9] beta-cyfluthrin , [c-4.10] cyhalothrin, [c-4.11] gamma-cyhalothrin, [c-4.12] lambda-cyhalothrin, [c-4. 13] cypermethrin, [c-4.14] alpha-cypermethrin, [c-4.15] beta-cypermethrin, [c-4.16] ceta - cypermethrin (theta-cypermethrin), [c-4.17] zeda-cypermethrin (zeta-cypermethrin), [c-4.18] cyphenothrin [(1R)-trans-isomer] (cyphenothrin [(1R) -trans-isomer]), [c-4.19] deltamethrin, [c-4.20] empenthrin [(EZ)-(1R)-isomer] (empenthrin [(EZ)-(1R)-isomer ]), [c-4.21] esfenvalerate, [c-4.22] ethofenprox, [c-4.23] fenpropathrin, [c-4. 24] fenvalerate, [c-4.25] flucythrinate, [c-4.26] flumethrin rin), [c-4.27] tau-fluvalinate, [c-4.28] halfenprox, [c-4.29] imiprothrin, [c-4 .30] methothrin, [c-4.31] metofluthrin, [c-4.32] epsilon-metofluthrin, [c-4.33] momfluorothrin, [c-4.34] epsilon-momfluorothrin, [c-4.35] permethrin, [c-4.36] phenothrin [(1R)-trans-isomer] (phenothrin [ (1R)-trans-isomer]), [c-4.37] prallethrin, [c-4.38] resmethrin, [c-4.39] kadethrin, [c-4 .40] silafluofen, [c-4.41] tefluthrin, [c-4.42] tetramethrin, [c-4.43] tetramethrin [(1R)-isomer] (tetramethrin [ (1R)-isomer]), [c-4.44] tralomethrin, [c-4.45] transfluthrin, [c-4.46] ZXI8901 (3-(4-bromophenoxy) phenyl]-cyanomethyl4-(difluoromethyl)-α-(1-methylethyl)benzeneacetate), [c-4.47] biopermethrin, [c-4.48] furamethrin, [c-4.49 ] profluthrin, [c-4.50] flubrocythrinate, [c-4.51] dimefluthrin, [c-4.52] DDT (dichloro-diphenyl-trichloroethane), [ c-4.53]methoxychlor, [c -4.54] phenothrin, [c-4.55] fluvalinate and the like.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

c-28: Other insecticides Other insecticides such as [c-28.1] azadirachtin, [c-28.2] benzoximate, [c-28.3] phenisobromo phenisobromolate, [c-28.4]chinomethionate, [c-28.5]dicofol, [c-28.6]pyridalyl, [c-28.7]bromopropoxy bromopropylate, [c-28.8] triazamate, [c-28.9] dicyclanil, [c-28.10] dinobuton, [c-28.11] dinocap ( dinocap), [c-28.12] hydrogen cyanide, [c-28.13] methyl iodide, [c-28.14] karanjin, [c-28.15] mercury chloride, [c-28.16] methyl isothiocyanate, [c-28.17] pentachlorophenol, [c-28.18] phosphine, [c -28.19] piperonyl butoxide, [c-28.20] polynactin complexes (polynactins), [c-28.21] sabadilla, [c-28.22] sulcofuron salts (sulcofuron- sodium (sulcofuron-sodium), [c-28.23] tribufos, [c-28.24] aldrin, [c-28.25] amidithion, [c-28.26 ] Amidothioate, [c-28.27] aminocarb, [c-28.28] amiton, [c-28.29] aramite, [c-28.30 ] athidathion, [c-28.31] azothoate, [c-28.32] polysulfide barium (barium polysulfide ), [c-28.33] benclothiaz, [c-28.34] 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone (5- (1,3-benzodioxole-5-yl)-3-hexylcyclohexa-2-enone), [c-28.35] 1,1-bis(4-chlorophenyl)-2-ethoxyethanol (1,1-bis( 4-chlorophenyl)-2-ethoxyethanol), [c-28.36] butonate, [c-28.37] butopyronoxyl, [c-28.38] 2-(2-butoxyethoxy) ethyl Thiocyanate (2-(2-butoxyethoxy)ethyl thiocyanate), [c-28.39] camphechlor, [c-28.40] chlorbenside, [c-28.41] chlordecone, [ c-28.42] chlordimeform, [c-28.43] chlorfenethol, [c-28.44] chlorfenson, [c-28.45] fluazuron , [c-28.46] metaldehyde, [c-28.47] bialaphos, [c-28.48] levamisol hydrochloride, [c-28.49] amidoflumet , [c-28.50] pyrafluprole, [c-28.51] pyriprole, [c-28.52] tralopyril, [c-28.53] flupyrazofos , [c-28.54] diofenolan, [c-28.55] chlorobenzylate, [c-28.56] flufenzine, [c-28.57] benzomate , [c-28.58] flufenerim, [c-28.59] albendazole, [c-28.60] oxybendazole dazole), [c-28.61] fenbendazole, [c-28.62] metam-sodium, [c-28.63] 1,3-dichloropropene (1,3 -dichloropropene), [c-28.64] flometoquin, [c-28.65] cyclaniliprole, [c-28.66] tetraniliprole, [c-28. 67] broflanilide, [c-28.68] dichloromezotiaz, [c-28.69] ethylene dibromide, [c-28.70] acrylonitrile, [ c-28.71] bis (2-chloroethyl) ether (bis (2-chloroethyl) ether), [c-28.72] 1-bromo-2-chloroethane (1-bromo-2-chloroethane), [c- 28.73]3-bromo-1-chloroprop-1-ene, [c-28.74]bromocyclen, [c-28.75]disulfide carbon disulfide, [c-28.76] tetrachloromethane, [c-28.77] nemadectin, [c-28.78] cymiazole [c-28.79] calcium polysulfide, [c-28.80] cytokinin, [c-28.81] 2-(octylthio)ethanol, [c-28.82] potassium oleate, [c -28.83] sodium oleate, [c-28.84] machine oil, [c-28.85] tar oil, [c-28.86] anabasine ( anabasine), [c-28.87] morantel tartrate, [c-28.88] pyrethrum, [c-28.89] rape seed oil), [c-28.90] soybean lecithin, [c-28.91] starch, [c-28.92] hydroxypropylstarch, [c-28.93] fatty acid decanoyloctanoylglycerol, [c-28.94] propylene glycol fatty acid ester, [c-28.95] diatomite, [c-28.96] afoxolaner, [c-28.97] fluazaindolizine, [c-28.98] afidopyropen, [c-28.99] cyhalodiamide, [c-28.100] tioxazafen , [c-28.101] fluhexafon, [c-28.102] fluralaner, [c-28.103] fluxametamide, [c-28.104] tetrachlorantrani tetrachlorantraniliprole, [c-28.105]sarolaner, [c-28.106]lotilaner, [c-28.107]cycloxaprid, [c-28.108]fluene fluensulfone, [c-28.109] TPIC (tripropyl isocyanurate), [c-28.110] DD (1,3-Dichloropropene), [c-28.111] peroxocarbonate, [c-28.112] MB-599 (verbutin), [c-28.113] bis (2,3,3,3-tetrachloropropyl) ether (bis (2,3,3,3-tetrachloropropyl) ether ), [c-28.114] DCIP (bis(2-chloro-1-methylethyl) ether), [c-28.115] ENT-8184 (N-(2-Ethylhexyl)bicyclo[2.2.1] hept-5-ene-2,3-dic ａｒｂｏｘｉｍｉｄｅ）、［ｃ－２８．１１６］Ｂａｙｅｒ ２２４０８（Ｏ，Ｏ－ｄｉｅｔｈｙｌ Ｏ－ｎａｐｈｔｈａｌｉｍｉｄｏ ｐｈｏｓｐｈｏｒｏｔｈｉｏａｔｅ）、［ｃ－２８．１１７］Ｂａｙｅｒ ３２３９４（ｔｒｉｓ（１－ｄｏｄｅｃｙｌ－３－ｍｅｔｈｙｌ－２－ｐｈｅｎｙｌｂｅｎｚｉｍｉｄａｚｏｌｉｕｍ）ｈｅｘａｃｙａｎｏｆｅｒｒａｔｅ） ,

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、国際特許第１５／１４４６８３号参照）、[c-28.122] formula (s38)

(see International Publication No. 14/053450, International Patent No. 15/144683),

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

(see International Publication No. 14/053450, International Patent No. 15/144683),

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

(see International Publication No. 14/053450, International Patent No. 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 of 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 of 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（特開平２７―１６０８１３号公報参照）、[c-28.127] formula (s43)

[In the formula, m8 represents an integer of 0 to 2. ] (see JP-A-27-160813),

［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、国際特許第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 Patent 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 WO 11/134964, WO 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 WO 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)

[Wherein, A57 represents a hydrogen atom, a fluorine atom, or a chlorine atom, and A58 is

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

［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)

[Wherein, A59 represents a hydrogen atom, a fluorine atom, or a chlorine atom, and A60 is

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

［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)

[Wherein, m10 represents an integer of 0 to 2, A61 represents a trifluoromethyl group, a trifluoromethylthio group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group, A62 represents a hydrogen atom, or represents a trifluoromethyl group, V6 represents a nitrogen atom or a carbon atom, and V7 represents an oxygen atom or an N-methyl group. ] (see WO 14/104407),

［式中、Ａ６３は、水素原子、またはフッ素原子を表し、アミド基は４位、または５位に結合し、Ａ６４は、

からなる群から選択される部分構造を表す。］で表される化合物（国際公開第１５／０３８５０３号、国際特許第１６／１４４３５１号、国際特許第１６／１４４６７８号参照）、[c-28.135] formula (s51)

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

represents a partial structure selected from the group consisting of ] (see International Publication No. 15/038503, International Patent No. 16/144351, International Patent No. 16/144678),

［式中、Ａ６５は、水素原子、Ｃ１～Ｃ６のアルキル基、またはＣ１～Ｃ６のハロアルキル基を表し、Ａ６６は、水素原子、ハロゲン原子、またはＣ１～Ｃ６のアルキル基を表し、Ａ６７およびＡ６８は、それぞれ独立していて、水素原子、シアノ基で適宜置換されてもよいＣ１～Ｃ６のアルキル基、メトキシ基で適宜置換されてもよいアルキル基、エトキシ基で適宜置換されてもよいアルキル基、またはＣ３～Ｃ８のシクロアルキル基を表し、
Ａ６９は、水素原子、シアノ基、シアノ基で適宜置換されてもよいＣ１～Ｃ６のハロアルキル基、Ｃ１～Ｃ６のアルキル基、またはＣ３～Ｃ８のシクロアルキル基を表す。］で表される化合物（国際公開第１２／１４３３１７号、国際特許第１６／０１６３６９号参照）、[c-28.136] formula (s52)

[In the formula, A65 represents a hydrogen atom, a C1-C6 alkyl group, or a C1-C6 haloalkyl group, A66 represents a hydrogen atom, a halogen atom, or a C1-C6 alkyl group, and A67 and A68 are , which are each independently a hydrogen atom, a C1 to C6 alkyl group optionally substituted with a cyano group, an alkyl group optionally substituted with a methoxy group, an alkyl group optionally substituted with an ethoxy group, or represents a C3-C8 cycloalkyl group,
A69 represents a hydrogen atom, a cyano group, a C1-C6 haloalkyl group optionally substituted with a cyano group, a C1-C6 alkyl group, or a C3-C8 cycloalkyl group. ] (see International Publication No. 12/143317, International Patent No. 16/016369),

［式中、Ａ７０は、メチル基、エチル基、イソプロピル基、２，２，２－トリフルオロエチル基、またはフェニル基を表し、Ａ７１は、

からなる群から選択される部分構造を表し、Ａ７２は、

からなる群から選択される部分構造を表し、Ｖ８は、酸素原子、硫黄原子、－ＣＨ_２－、または－ＣＨ_２ＣＨ_２－を表す。］で表される化合物（国際公開第１４／１６７０８４号、国際特許第１６／０５５４３１号参照）、[c-28.137] formula (s53) or formula (s54)

[Wherein, A70 represents a methyl group, an ethyl group, an isopropyl group, a 2,2,2-trifluoroethyl group, or a phenyl group;

A72 represents a partial structure selected from the group consisting of

represents a partial structure selected from the group consisting of V8 represents an oxygen atom, a sulfur atom, —CH ₂ —, or —CH ₂ CH ₂ —. ] (see International Publication No. 14/167084, International Patent No. 16/055431),

［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)

[Wherein, m11 represents an integer of 0 to 1, A73 represents a chlorine atom, a bromine atom, a methyl group, or a trifluoromethyl group, A74 represents a hydrogen atom, a chlorine atom, a bromine atom, a cyano group, or represents a trifluoromethyl group, A75 represents a hydrogen atom, a chlorine atom or a bromine atom, A76 and A77 each independently represent a C1-C6 alkyl group or a C3-C8 cycloalkyl group, A78 represents a chlorine atom, a bromine atom, a cyano group, a nitro group, a difluoromethyl group, or a trifluoromethyl group. ] (see WO 13/024009),

［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)

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

［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)

[Wherein, m12 represents an integer of 0 to 2, A83 represents a hydrogen atom or a fluorine atom, and A84 represents

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

［Ａ９０は、ハロゲン原子、Ｃ１～Ｃ６のアルキル基、またはＣ１～Ｃ６のハロアルキル基を表し、Ａ９１は、Ｃ１～Ｃ６のハロアルキル基を表し、Ａ９２およびＡ９３は、それぞれ独立していて、水素原子、Ｃ１～Ｃ６のアルキル基、アセチル基、プロピオノイル基、メタンスルホニルエチル基、メトキシカルボニル基、またはエトキシカルボニル基を表し、Ａ９４およびＡ９５は、それぞれ独立していて、水素原子、Ｃ１～Ｃ６のアルキル基、またはＣ１～Ｃ６のハロアルキル基を表す。］で表される化合物（国際公開第１２／１６４６９８号参照）等が挙げられる。[c-28.141] acynonapyr,
[c-28.142] formula (s59)

[A90 represents a halogen atom, a C1-C6 alkyl group, or a C1-C6 haloalkyl group, A91 represents a C1-C6 haloalkyl group, A92 and A93 are each independently a hydrogen atom, represents a C1-C6 alkyl group, an acetyl group, a propionoyl group, a methanesulfonylethyl group, a methoxycarbonyl group, or an ethoxycarbonyl group, A94 and A95 each independently represent a hydrogen atom, a C1-C6 alkyl group, or represents a C1-C6 haloalkyl group. ] (see International Publication No. 12/164698) and the like.

The mixing ratio of the compound of the present invention and the pest control agent is not particularly limited as long as the effect is exhibited. A ratio of 1000, preferably a ratio of 0.01 to 100.

The present invention will be illustrated in more detail below by giving Synthesis Examples, Reference Examples, and Test Examples, but the present invention is not limited to these.

５－アセチル－３－クロロ－６－（２，６－ジフルオロフェニル）－１－エチルピリジン－２（１Ｈ）－オン １８０ｍｇ、Ｏ－メチルヒドロキシルアミン塩酸塩 ５８ｍｇとピリジン ９４μｌを含むエタノール溶液 ４ｍｌを還流下で１．５時間撹拌した。減圧下で溶媒留去した後に、反応混合物に１規定塩酸と酢酸エチルを加えて分液した。得られた有機層を飽和炭酸水素ナトリウム水溶液と飽和食塩水で順次洗浄し、硫酸ナトリウムで乾燥した。減圧下で溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物は異性体混合物として得られ、主成分が低極性成分である白色固体を１２２ｍｇ、主成分が高極性成分である白色固体を２８ｍｇ得た。前者が化合物番号１であり、その成分比率は＞９９：＜１（低極性：高極性）であった。一方、後者は化合物番号２であり、その成分比は１６：８４（低極性：高極性）であった。[Synthesis Example 1]
Synthesis of 3-chloro-6-(2,6-difluorophenyl)-1-ethyl-5-(1-(methoxyimino)ethyl)pyridin-2(1H)-one (compound numbers: A-001 and A- 002)

4 ml of an ethanol solution containing 180 mg of 5-acetyl-3-chloro-6-(2,6-difluorophenyl)-1-ethylpyridin-2(1H)-one, 58 mg of O-methylhydroxylamine hydrochloride and 94 μl of pyridine was refluxed. Stir under low heat for 1.5 hours. After the solvent was distilled off under reduced pressure, 1N hydrochloric acid and ethyl acetate were added to the reaction mixture to separate the layers. The obtained organic layer was washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over sodium sulfate. After evaporating the solvent under reduced pressure, the obtained residue was purified by silica gel column chromatography. The title compound was obtained as an isomer mixture, and 122 mg of a white solid whose main component was a low polar component and 28 mg of a white solid whose main component was a high polar component were obtained. The former was Compound No. 1, and its component ratio was >99:<1 (low polarity: high polarity). On the other hand, the latter was Compound No. 2, and its component ratio was 16:84 (low polarity:high polarity).

参考例１～６を参考にして調製した５－クロロ－２－（２，４，６－トリフルオロフェニル）－１－エチル－６－オキソ－１，６－ジヒドロピリジン－３－カルボアルデヒド ３．０６ｇ、ヒドロキシルアミン塩酸塩 ７４３ｍｇとピリジン ８６１μｌを含むエタノール溶液 ３０ｍｌを室温で１時間撹拌した。反応混合物に１規定塩酸と酢酸エチルを加えて分液した後に、得られた有機層を飽和食塩水で洗浄し、硫酸ナトリウムで乾燥した。減圧下で溶媒留去した後に、表題の化合物を含む３．３０ｇの黄色アモルファスが得られた。これ以上精製することなく、次の反応に使用した。[Synthesis Example 2]
Step 1: Synthesis of 5-chloro-1-ethyl-6-oxo-2-(2,4,6-trifluorophenyl)-1,6-dihydropyridine-3-carbaldehyde oxime

3.06 g of 5-chloro-2-(2,4,6-trifluorophenyl)-1-ethyl-6-oxo-1,6-dihydropyridine-3-carbaldehyde prepared with reference to Reference Examples 1 to 6 , 30 ml of an ethanol solution containing 743 mg of hydroxylamine hydrochloride and 861 μl of pyridine was stirred at room temperature for 1 hour. 1N Hydrochloric acid and ethyl acetate were added to the reaction mixture and the layers were separated, and the resulting organic layer was washed with saturated brine and dried over sodium sulfate. After evaporation of the solvent under reduced pressure, 3.30 g of a yellow amorphous containing the title compound were obtained. Used for next reaction without further purification.

ステップ１で得られた５－クロロ－１－エチル－６－オキソ－２－（２，４，６－トリフルオロフェニル）－１，６－ジヒドロピリジン－３－カルバルデヒド オキシム ３００ｍｇとＮ－クロロスクシンイミド １３３ｍｇを含むＤＭＦ溶液 ３ｍｌを５０℃で４０分間撹拌した。室温まで冷却した後に、反応混合物に水と酢酸エチルを加えて分液した。得られた有機層を飽和食塩水で洗浄し、硫酸ナトリウムで乾燥した。減圧下で溶媒留去した後に、表題の化合物を含む３５６ｍｇの黄色アモルファスが得られた。これ以上精製することなく、次の反応に使用した。 ¹ H-NMR (CDCl ₃ ) δ: 8.13 (1H, s), 7.36 (1H, s), 7.24 (1H, s), 6.92-6.88 (2H, m), 3.88 (2H, q, J = 7.2 Hz), 1.15 (3H, t, J = 7.2 Hz).
Step 2: Synthesis of 5-chloro-1-ethyl-N-hydroxy-6-oxo-2-(2,4,6-trifluorophenyl)-1,6-dihydropyridine-3-carbimidoyl chloride

300 mg of 5-chloro-1-ethyl-6-oxo-2-(2,4,6-trifluorophenyl)-1,6-dihydropyridine-3-carbaldehyde oxime obtained in Step 1 and 133 mg of N-chlorosuccinimide 3 ml of a DMF solution containing was stirred at 50° C. for 40 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 saline and dried with sodium sulfate. After evaporating the solvent under reduced pressure, 356 mg of a yellow amorphous was obtained containing the title compound. Used for next reaction without further purification.

ステップ１で得られた５－クロロ－１－エチル－Ｎ－ヒドロキシ－６－オキソ－２－（２，４，６－トリフルオロフェニル）－１，６－ジヒドロピリジン－３－カルビミドイルクロリド １５２ｍｇを含むＴＨＦ溶液 ４ｍｌに、イソプロピルマグネシウムクロリドのＴＨＦ溶液（２．０ｍｏｌ／Ｌ） ６２４μｌを－７８℃で滴下して３．５時間撹拌した。反応混合物に飽和塩化アンモニウム水溶液と酢酸エチルを加えて分液した後に、得られた有機層を飽和食塩水で洗浄し、硫酸ナトリウムで乾燥した。減圧下で溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が９５ｍｇの黄色アモルファスとして得られた。Step 3: Synthesis of 3-chloro-1-ethyl-5-(1-(hydroxyimino)-2-methylpropyl)-6-(2,4,6-trifluorophenyl)pyridin-2(1H)-one (Compound number: A-009)

152 mg of 5-chloro-1-ethyl-N-hydroxy-6-oxo-2-(2,4,6-trifluorophenyl)-1,6-dihydropyridine-3-carbimidoyl chloride obtained in Step 1 was 624 μl of a THF solution of isopropylmagnesium chloride (2.0 mol/L) was added dropwise to 4 ml of the THF solution containing the mixture at −78° C. and stirred for 3.5 hours. A saturated aqueous ammonium chloride solution and ethyl acetate were added to the reaction mixture and the mixture was separated, and the obtained organic layer was washed with saturated brine and dried over sodium sulfate. After evaporating the solvent under reduced pressure, the obtained residue was purified by silica gel column chromatography. 95 mg of the title compound was obtained as a yellow amorphous.

３－クロロ－１－エチル－５－（１－（ヒドロキシイミノ）－２－メチルプロピル）－６－（２，４，６－トリフルオロフェニル）ピリジン－２（１Ｈ）－オン ６９．８ｍｇ、ヨウ化メチル ２３．３μｌと酸化銀（Ｉ） ８６．８ｍｇを含むジクロロメタン溶液 ２ｍｌを室温で１１時間撹拌した。さらに、ヨウ化メチル ２３．３μｌと酸化銀（Ｉ） ８６．８ｍｇを追加して、室温で２時間撹拌した。得られた反応混合物を濾過することにより不溶物を除去した。濾液を減圧下にて溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が４８ｍｇの白色固体として得られた。[Synthesis Example 3]
Synthesis of 3-chloro-1-ethyl-5-(1-(methoxyimino)-2-methylpropyl)-6-(2,4,6-trifluorophenyl)pyridin-2(1H)-one (Compound No. : A-010)

3-chloro-1-ethyl-5-(1-(hydroxyimino)-2-methylpropyl)-6-(2,4,6-trifluorophenyl)pyridin-2(1H)-one 69.8 mg, iodine 2 ml of a dichloromethane solution containing 23.3 μl of methyl chloride and 86.8 mg of silver (I) oxide was stirred at room temperature for 11 hours. Furthermore, 23.3 μl of methyl iodide and 86.8 mg of silver (I) oxide were added, and the mixture was stirred at room temperature for 2 hours. The insoluble matter was removed by filtering the obtained reaction mixture. After evaporating the filtrate under reduced pressure, the resulting residue was purified by silica gel column chromatography. 48 mg of the title compound was obtained as a white solid.

５－クロロ－１－エチル－６－オキソ－２－（２，４，６－トリフルオロフェニル）－１，６－ジヒドロピリジン－３－カルバルデヒド オキシム ２０３ｍｇとＮ－クロロスクシンイミド １２３ｍｇを含むＴＨＦ溶液 ５ｍｌを５０℃で１時間撹拌した。室温まで冷却した後に、エチルビニルエーテル ２９５μｌとトリエチルアミン ９５μｌを加えて、室温で１０分間撹拌した。反応混合物に飽和炭酸水素ナトリウム水溶液と酢酸エチルを加えて分液した後に、得られた有機層を飽和食塩水で洗浄し、硫酸ナトリウムで乾燥した。濾液を減圧下にて溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が２１７ｍｇの淡黄色ガム状物質として得られた。[Synthesis Example 4]
3-chloro-5-(5-ethoxy-4,5-dihydroisoxazol-3-yl)-1-ethyl-6-(2,4,6-trifluorophenyl)pyridin-2(1H)-one Synthesis of (compound number: C-001)

5 ml of THF solution containing 203 mg of 5-chloro-1-ethyl-6-oxo-2-(2,4,6-trifluorophenyl)-1,6-dihydropyridine-3-carbaldehyde oxime and 123 mg of N-chlorosuccinimide Stir at 50° C. for 1 hour. After cooling to room temperature, 295 μl of ethyl vinyl ether and 95 μl of triethylamine were added and stirred at room temperature for 10 minutes. A saturated aqueous solution of sodium hydrogencarbonate and ethyl acetate were added to the reaction mixture and the mixture was separated, and then the resulting organic layer was washed with saturated brine and dried over sodium sulfate. After evaporating the filtrate under reduced pressure, the resulting residue was purified by silica gel column chromatography. 217 mg of the title compound was obtained as a pale yellow gum.

ステップ１で得られた３－クロロ－５－（５－エトキシ－４，５－ジヒドロイソキサゾール－３－イル）－１－エチル－６－（２，４，６－トリフルオロフェニル）ピリジン－２（１Ｈ）－オン １６９ｍｇとｐ－トルエンスルホン酸一水和物 ７ｍｇを含むトルエン溶液 ４ｍｌを還流下で１５分間撹拌した。さらにｐ－トルエンスルホン酸一水和物 ６５ｍｇを追加して、還流下で１時間撹拌した。室温まで冷却した後に、反応混合物に飽和炭酸水素ナトリウム水溶液と酢酸エチルを加えて分液した。得られた有機層を飽和食塩水で洗浄し、硫酸ナトリウムで乾燥した。濾液を減圧下にて溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が１３２ｍｇの白色固体として得られた。[Synthesis Example 5]
Synthesis of 3-chloro-1-ethyl-5-(isoxazol-3-yl)-6-(2,4,6-trifluorophenyl)pyridin-2(1H)-one (Compound No.: B-001)

3-chloro-5-(5-ethoxy-4,5-dihydroisoxazol-3-yl)-1-ethyl-6-(2,4,6-trifluorophenyl)pyridine- obtained in step 1 4 ml of a toluene solution containing 169 mg of 2(1H)-one and 7 mg of p-toluenesulfonic acid monohydrate was stirred under reflux for 15 minutes. Further, 65 mg of p-toluenesulfonic acid monohydrate was added, and the mixture was stirred under reflux for 1 hour. After cooling to room temperature, saturated aqueous sodium hydrogencarbonate solution and ethyl acetate were added to the reaction mixture to separate the layers. The obtained organic layer was washed with saturated saline and dried with sodium sulfate. After evaporating the filtrate under reduced pressure, the resulting residue was purified by silica gel column chromatography. 132 mg of the title compound was obtained as a white solid.

３－クロロ－１－エチル－５－（イソキサゾール－３－イル）－６－（２，４，６－トリフルオロフェニル）ピリジン－２（１Ｈ）－オン ６０３ｍｇと臭素 １．４６ｍｌを含む酢酸溶液 １７ｍｌを１２０℃で５時間撹拌した。さらに、臭素 ９７３μｌを追加して、１２０℃で３時間撹拌した。室温まで冷却した後に、反応混合物にチオ硫酸ナトリウム水溶液と酢酸エチルを加えて分液した。得られた有機層を飽和炭酸水素ナトリウム水溶液と飽和食塩水で順次洗浄し、硫酸ナトリウムで乾燥した。濾液を減圧下にて溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が２４９ｍｇの白色固体として得られた。[Synthesis Example 6]
Synthesis of 5-(4-bromoisoxazol-3-yl)-3-chloro-1-ethyl-6-(2,4,6-trifluorophenyl)pyridin-2(1H)-one (compound number: B-002)

17 ml of acetic acid solution containing 603 mg of 3-chloro-1-ethyl-5-(isoxazol-3-yl)-6-(2,4,6-trifluorophenyl)pyridin-2(1H)-one and 1.46 ml of bromine was stirred at 120° C. for 5 hours. Further, 973 µl of bromine was added, and the mixture was stirred at 120°C for 3 hours. After cooling to room temperature, an aqueous sodium thiosulfate solution and ethyl acetate were added to the reaction mixture to separate the layers. The obtained organic layer was washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over sodium sulfate. After evaporating the filtrate under reduced pressure, the resulting residue was purified by silica gel column chromatography. 249 mg of the title compound was obtained as a white solid.

５－クロロ－１－エチル－６－オキソ－２－（２，４，６－トリフルオロフェニル）－１，６－ジヒドロピリジン－３－カルバルデヒド オキシム ２０９ｍｇとＮ－クロロスクシンイミド ９３ｍｇを含むＴＨＦ溶液 ５ｍｌを５０℃で１１０分間撹拌した。さらにＮ－クロロスクシンイミド ４２ｍｇを追加して、５０℃で４０分間撹拌した。室温まで冷却した後に、トリメチルシリルアセチレン ４３７μｌとトリエチルアミン ９８μｌを加えて、室温で１５分間撹拌した。反応混合物に飽和炭酸水素ナトリウム水溶液と酢酸エチルを加えて分液した後に、得られた有機層を飽和食塩水で洗浄し、硫酸ナトリウムで乾燥した。濾液を減圧下にて溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が２４１ｍｇの白色固体として得られた。[Synthesis Example 7]
Step 1: Synthesis of 3-chloro-1-ethyl-6-(2,4,6-trifluorophenyl)-5-(5-(trimethylsilyl)isoxazol-3-yl)pyridin-2(1H)-one ( Compound number: B-004)

5-chloro-1-ethyl-6-oxo-2-(2,4,6-trifluorophenyl)-1,6-dihydropyridine-3-carbaldehyde oxime 209mg and N-chlorosuccinimide 93mg of THF solution 5ml Stir at 50° C. for 110 minutes. Further, 42 mg of N-chlorosuccinimide was added, and the mixture was stirred at 50°C for 40 minutes. After cooling to room temperature, 437 μl of trimethylsilylacetylene and 98 μl of triethylamine were added and stirred at room temperature for 15 minutes. A saturated aqueous solution of sodium hydrogencarbonate and ethyl acetate were added to the reaction mixture and the mixture was separated, and then the resulting organic layer was washed with saturated brine and dried over sodium sulfate. After evaporating the filtrate under reduced pressure, the resulting residue was purified by silica gel column chromatography. 241 mg of the title compound was obtained as a white solid.

３－クロロ－１－エチル－６－（２，４，６－トリフルオロフェニル）－５－（５－（トリメチルシリル）イソキサゾール－３－イル）ピリジン－２（１Ｈ）－オン ８８ｍｇとＮ－ブロモスクシンイミド ４４ｍｇを含むＤＭＦ溶液 ２ｍｌを８０℃で２０分間撹拌した後、１２０℃で１．５時間撹拌した。さらにＮ－ブロモスクシンイミド １４７ｍｇを追加して、１２０℃で５５分間撹拌した。室温まで冷却した後に、反応混合物に水と酢酸エチルを加えて分液した。得られた有機層をチオ硫酸ナトリウム水溶液と飽和食塩水で順次洗浄し、硫酸ナトリウムで乾燥した。濾液を減圧下にて溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。高極性成分である白色固体を３１ｍｇ、低極性成分である白色固体を３０ｍｇ得た。前者が化合物番号Ｂ－００３であり、後者は化合物番号Ｂ－００５であった。[Synthesis Example 8]
3-chloro-5-(4,5-dibromoisoxazol-3-yl)-1-ethyl-6-(2,4,6-trifluorophenyl)pyridin-2(1H)-one (compound number: B-003) and 5-(4-bromo-5-(trimethylsilyl)isoxazol-3-yl)-3-chloro-1-ethyl-6-(2,4,6-trifluorophenyl)pyridine-2(1H )-one synthesis (compound number: B-005)

3-chloro-1-ethyl-6-(2,4,6-trifluorophenyl)-5-(5-(trimethylsilyl)isoxazol-3-yl)pyridin-2(1H)-one 88 mg and N-bromosuccinimide 2 ml of a DMF solution containing 44 mg was stirred at 80°C for 20 minutes and then stirred at 120°C for 1.5 hours. Further, 147 mg of N-bromosuccinimide was added, and the mixture was stirred at 120°C for 55 minutes. After cooling to room temperature, 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 filtrate under reduced pressure, the resulting residue was purified by silica gel column chromatography. 31 mg of a white solid, which is a highly polar component, and 30 mg of a white solid, which is a low polar component, were obtained. The former was Compound No. B-003 and the latter was Compound No. B-005.

３－クロロ－１－エチル－６－（２，４，６－トリフルオロフェニル）－５－（５－（トリメチルシリル）イソキサゾール－３－イル）ピリジン－２（１Ｈ）－オン ２５０ｍｇとＮ－クロロスクシンイミド １０２ｍｇを含む酢酸溶液 ５ｍｌを１００℃で４０分間撹拌した。さらに、Ｎ－クロロスクシンイミド １０２ｍｇを追加して、１００℃で１．５時間撹拌した。室温まで冷却した後に、反応混合物に飽和炭酸水素ナトリウム水溶液と酢酸エチルを加えて分液した。得られた有機層を飽和食塩水で洗浄し、硫酸ナトリウムで乾燥した。濾液を減圧下にて溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が７３ｍｇの白色固体として得られた。[Synthesis Example 9]
Step 1: 3-Chloro-5-(4-chloro-5-(trimethylsilyl)isoxazol-3-yl)-1-ethyl-6-(2,4,6-trifluorophenyl)pyridine-2(1H)- Composite on

3-chloro-1-ethyl-6-(2,4,6-trifluorophenyl)-5-(5-(trimethylsilyl)isoxazol-3-yl)pyridin-2(1H)-one 250 mg and N-chlorosuccinimide 5 ml of acetic acid solution containing 102 mg was stirred at 100° C. for 40 minutes. Further, 102 mg of N-chlorosuccinimide was added, and the mixture was stirred at 100° C. for 1.5 hours. After cooling to room temperature, saturated aqueous sodium hydrogencarbonate solution and ethyl acetate were added to the reaction mixture to separate the layers. The obtained organic layer was washed with saturated saline and dried with sodium sulfate. After evaporating the filtrate under reduced pressure, the resulting residue was purified by silica gel column chromatography. The title compound was obtained as 73 mg of white solid.

３－クロロ－５－（４－クロロ－５－（トリメチルシリル）イソキサゾール－３－イル）－１－エチル－６－（２，４，６－トリフルオロフェニル）ピリジン－２（１Ｈ）－オン ９６ｍｇを含むアセトニトリル溶液 ３ｍｌに、エタノール １ｍｌとフッ化セシウム ４１ｍｇを加えて室温で５分撹拌した。反応混合物に飽和塩化アンモニウム水溶液と酢酸エチルを加えて分液した後に、得られた有機層を飽和食塩水で洗浄し、硫酸ナトリウムで乾燥した。減圧下で溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が７１ｍｇの白色固体として得られた。 ¹ H-NMR (CDCl ₃ ) δ: 7.71 (1H, s), 6.74-6.72 (2H, m), 3.98 (2H, q, J = 7.2 Hz), 19 (3H, t, J = 7.2 Hz), 0.36 (9H, s).
Step 2: Synthesis of 3-chloro-5-(4-chloroisoxazol-3-yl)-1-ethyl-6-(2,4,6-trifluorophenyl)pyridin-2(1H)-one ( Compound number: B-006)

3-chloro-5-(4-chloro-5-(trimethylsilyl)isoxazol-3-yl)-1-ethyl-6-(2,4,6-trifluorophenyl)pyridin-2(1H)-one 96 mg 1 ml of ethanol and 41 mg of cesium fluoride were added to 3 ml of the acetonitrile solution containing the mixture, and the mixture was stirred at room temperature for 5 minutes. A saturated aqueous ammonium chloride solution and ethyl acetate were added to the reaction mixture and the mixture was separated, and the obtained organic layer was washed with saturated brine and dried over sodium sulfate. After evaporating the solvent under reduced pressure, the obtained residue was purified by silica gel column chromatography. The title compound was obtained as 71 mg of white solid.

５－クロロ－１－エチル－Ｎ－ヒドロキシ－６－オキソ－２－（２，４，６－トリフルオロフェニル）－１，６－ジヒドロピリジン－３－カルビミドイル クロリド ２８８ｍｇを含むＴＨＦ溶液 ３ｍｌに、イソプロペニルマグネシウムブロミドのＴＨＦ溶液（０．５ｍｏｌ／Ｌ） ４．７３ｍｌを－７８℃で滴下して３０分間撹拌した。反応混合物に飽和塩化アンモニウム水溶液と酢酸エチルを加えて分液した後に、得られた有機層を飽和食塩水で洗浄し、硫酸ナトリウムで乾燥した。減圧下で溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が１７９ｍｇの白色アモルファスとして得られた。[Synthesis Example 10]
Step 1: Synthesis of 3-chloro-1-ethyl-5-(1-(hydroxyimino)-2-methylallyl)-6-(2,4,6-trifluorophenyl)pyridin-2(1H)-one

Isopropenyl 4.73 ml of a THF solution (0.5 mol/L) of magnesium bromide was added dropwise at -78°C and stirred for 30 minutes. A saturated aqueous ammonium chloride solution and ethyl acetate were added to the reaction mixture and the mixture was separated, and the obtained organic layer was washed with saturated brine and dried over sodium sulfate. After evaporating the solvent under reduced pressure, the obtained residue was purified by silica gel column chromatography. 179 mg of the title compound was obtained as a white amorphous.

３－クロロ－１－エチル－５－（１－（ヒドロキシイミノ）－２－メチルアリル）－６－（２，４，６－トリフルオロフェニル）ピリジン－２（１Ｈ）－オン １７９ｍｇを含むＴＨＦ溶液 ４ｍｌに炭酸水素ナトリウム １６２ｍｇを含む水溶液 ３ｍｌを室温で加えた。これにヨウ素 １３５ｍｇとヨウ化カリウム ２８１ｍｇの水溶液 ３ｍｌを加えて、還流下で５０分間撹拌した。室温まで冷却した後に、反応混合物にチオ硫酸ナトリウム水溶液と酢酸エチルを加えて分液した。得られた有機層を飽和食塩水で洗浄し、硫酸ナトリウムで乾燥した。減圧下で溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が２０ｍｇの白色固体として得られた。 ¹ H-NMR (CDCl ₃ ) δ: 7.62 (1H, s), 7.09 (1H, br s), 6.80-6.78 (2H, m), 5.24-5.23 ( 1H, m), 4.99-4.97 (1H, m), 3.90 (2H, q, J = 7.2 Hz), 1.75 (3H, s), 1.15 (3H, t , J=7.2 Hz).
Step 2: Synthesis of 3-chloro-1-ethyl-5-(4-methylisoxazol-3-yl)-6-(2,4,6-trifluorophenyl)pyridin-2(1H)-one ( Compound number: B-008)

4 ml of THF solution containing 179 mg of 3-chloro-1-ethyl-5-(1-(hydroxyimino)-2-methylallyl)-6-(2,4,6-trifluorophenyl)pyridin-2(1H)-one 3 ml of an aqueous solution containing 162 mg of sodium hydrogencarbonate was added to the solution at room temperature. 3 ml of an aqueous solution containing 135 mg of iodine and 281 mg of potassium iodide was added thereto, and the mixture was stirred under reflux for 50 minutes. After cooling to room temperature, an aqueous sodium thiosulfate solution and ethyl acetate were added to the reaction mixture to separate the layers. The obtained organic layer was washed with saturated saline and dried with sodium sulfate. After evaporating the solvent under reduced pressure, the obtained residue was purified by silica gel column chromatography. 20 mg of the title compound was obtained as a white solid.

５－クロロ－１－エチル－Ｎ－ヒドロキシ－６－オキソ－２－（２，４，６－トリフルオロフェニル）－１，６－ジヒドロピリジン－３－カルビミドイル クロリド ３７８ｍｇに、１－プロピンのＴＨＦ溶液（２．０ｍｏｌ／Ｌ） ３１ｍｌとトリエチルアミン １６０μｌを加えて、室温で２時間撹拌した。反応混合物に飽和炭酸水素ナトリウム水溶液と酢酸エチルを加えて分液した後に、得られた有機層を飽和食塩水で洗浄し、硫酸ナトリウムで乾燥した。濾液を減圧下にて溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が２８７ｍｇの白色固体として得られた。[Synthesis Example 11]
Synthesis of 3-chloro-1-ethyl-5-(5-methylisoxazol-3-yl)-6-(2,4,6-trifluorophenyl)pyridin-2(1H)-one (compound number: B-013)

To 378 mg of 5-chloro-1-ethyl-N-hydroxy-6-oxo-2-(2,4,6-trifluorophenyl)-1,6-dihydropyridine-3-carbimidoyl chloride, THF solution of 1-propyne ( 2.0 mol/L) 31 ml and triethylamine 160 μl were added and stirred at room temperature for 2 hours. A saturated aqueous solution of sodium hydrogencarbonate and ethyl acetate were added to the reaction mixture and the mixture was separated, and then the resulting organic layer was washed with saturated brine and dried over sodium sulfate. After evaporating the filtrate under reduced pressure, the resulting residue was purified by silica gel column chromatography. 287 mg of the title compound was obtained as a white solid.

３－クロロ－１－エチル－５－（５－メチルイソキサゾール－３－イル）－６－（２，４，６－トリフルオロフェニル）ピリジン－２（１Ｈ）－オン ２８７ｍｇとＮ－ブロモスクシンイミド ２０８ｍｇを含む酢酸溶液 ３ｍｌを８０℃で２０分間撹拌した後、１００℃で４時間撹拌した。さらに、Ｎ－ブロモスクシンイミド ６９ｍｇを追加して、１００℃で１時間撹拌した。室温まで冷却した後に、反応混合物にチオ硫酸ナトリウム水溶液と酢酸エチルを加えて分液した。得られた有機層を飽和炭酸水素ナトリウム水溶液と飽和食塩水で順次洗浄し、硫酸ナトリウムで乾燥した。濾液を減圧下にて溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が２６８ｍｇの白色固体として得られた。[Synthesis Example 12]
Synthesis of 5-(4-bromo-5-methylisoxazol-3-yl)-3-chloro-1-ethyl-6-(2,4,6-trifluorophenyl)pyridin-2(1H)-one (Compound number: B-014)

3-chloro-1-ethyl-5-(5-methylisoxazol-3-yl)-6-(2,4,6-trifluorophenyl)pyridin-2(1H)-one 287 mg and N-bromosuccinimide After stirring 3 ml of an acetic acid solution containing 208 mg at 80° C. for 20 minutes, it was stirred at 100° C. for 4 hours. Further, 69 mg of N-bromosuccinimide was added, and the mixture was stirred at 100°C for 1 hour. After cooling to room temperature, an aqueous sodium thiosulfate solution and ethyl acetate were added to the reaction mixture to separate the layers. The obtained organic layer was washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over sodium sulfate. After evaporating the filtrate under reduced pressure, the resulting residue was purified by silica gel column chromatography. 268 mg of the title compound was obtained as a white solid.

５－クロロ－１－エチル－６－オキソ－２－（２，４，６－トリフルオロフェニル）－１，６－ジヒドロピリジン－３－カルバルデヒド オキシム ３０５ｍｇとＮ－クロロスクシンイミド １８５ｍｇを含むＴＨＦ溶液 ６ｍｌを５０℃で５５分間撹拌した。室温まで冷却した後に、２－プロピン－１－オール ２７２μｌとトリエチルアミン １４３μｌを加えて、室温で５０分間撹拌した。反応混合物に飽和炭酸水素ナトリウム水溶液と酢酸エチルを加えて分液した後に、得られた有機層を飽和食塩水で洗浄し、硫酸ナトリウムで乾燥した。濾液を減圧下にて溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が２８１ｍｇの白色アモルファスとして得られた。[Synthesis Example 13]
Synthesis of 3-chloro-1-ethyl-5-(5-(hydroxymethyl)isoxazol-3-yl)-6-(2,4,6-trifluorophenyl)pyridin-2(1H)-one (Compound No. : B-019)

6 ml of THF solution containing 305 mg of 5-chloro-1-ethyl-6-oxo-2-(2,4,6-trifluorophenyl)-1,6-dihydropyridine-3-carbaldehyde oxime and 185 mg of N-chlorosuccinimide Stir at 50° C. for 55 minutes. After cooling to room temperature, 272 μl of 2-propyn-1-ol and 143 μl of triethylamine were added and stirred at room temperature for 50 minutes. A saturated aqueous solution of sodium hydrogencarbonate and ethyl acetate were added to the reaction mixture and the mixture was separated, and then the resulting organic layer was washed with saturated brine and dried over sodium sulfate. After evaporating the filtrate under reduced pressure, the resulting residue was purified by silica gel column chromatography. 281 mg of the title compound was obtained as a white amorphous.

３－クロロ－１－エチル－５－（５－（ヒドロキシメチル）イソキサゾール－３－イル）－６－（２，４，６－トリフルオロフェニル）ピリジン－２（１Ｈ）－オン ２４８ｍｇとＮ－ブロモスクシンイミド １７２ｍｇを含むＤＭＦ溶液 ３ｍｌを７０℃で２０分間撹拌した後、１００℃で１時間撹拌した。さらに、Ｎ－ブロモスクシンイミド １７２ｍｇを追加して、１００℃で１時間撹拌した。室温まで冷却した後に、反応混合物に水と酢酸エチルを加えて分液した。得られた有機層をチオ硫酸ナトリウム水溶液と飽和食塩水で順次洗浄して、硫酸ナトリウムで乾燥した。濾液を減圧下にて溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物を含む１７６ｍｇの黄色固体が得られた。これ以上精製することなく、次の反応に使用した。[Synthesis Example 14]
Step 1: 5-(4-bromo-5-(hydroxymethyl)isoxazol-3-yl)-3-chloro-1-ethyl-6-(2,4,6-trifluorophenyl)pyridine-2(1H) -Synthesis of on

3-chloro-1-ethyl-5-(5-(hydroxymethyl)isoxazol-3-yl)-6-(2,4,6-trifluorophenyl)pyridin-2(1H)-one 248 mg and N-bromo 3 ml of a DMF solution containing 172 mg of succinimide was stirred at 70°C for 20 minutes and then stirred at 100°C for 1 hour. Further, 172 mg of N-bromosuccinimide was added, and the mixture was stirred at 100° C. for 1 hour. After cooling to room temperature, 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 filtrate under reduced pressure, the resulting residue was purified by silica gel column chromatography. 176 mg of a yellow solid containing the title compound was obtained. Used for next reaction without further purification.

¹ H-NMR (CDCl ₃ ) δ: 7.67 (1H, s), 6.76-6.71 (2H, m), 4.73 (2H, d, J = 6.6 Hz), 3. 97 (2H, q, J = 7.1 Hz), 1.97 (1H, t, J = 6.6 Hz) 1.20 (3H, t, J = 7.1 Hz).

ステップ１で得られた５－（４－ブロモ－５－（ヒドロキシメチル）イソキサゾール－３－イル）－３－クロロ－１－エチル－６－（２，４，６－トリフルオロフェニル）ピリジン－２（１Ｈ）－オン １７６ｍｇのジクロロメタン溶液 ４ｍｌに、デス・マーチン試薬（１，１，１－トリアセトキシ－１，１－ジヒドロ－１，２－ベンズヨードキソール－３（１Ｈ）－オン） １７７ｍｇを加えて室温で撹拌した。さらに１時間後と５．５時間後に、デス・マーチン試薬 １７７ｍｇをそれぞれ追加し、室温で１０５分間撹拌した。反応混合物に飽和炭酸水素ナトリウム水溶液と酢酸エチルを加えて分液した。得られた有機層をチオ硫酸ナトリウム水溶液と飽和食塩水で順次洗浄して、硫酸ナトリウムで乾燥した。濾液を減圧下にて溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が９４ｍｇの白色固体として得られた。Step 2: 4-bromo-3-(5-chloro-1-ethyl-6-oxo-2-(2,4,6-trifluorophenyl)-1,6-dihydropyridin-3-yl)isoxazole-5- Synthesis of carbaldehyde (compound number: B-020)

5-(4-bromo-5-(hydroxymethyl)isoxazol-3-yl)-3-chloro-1-ethyl-6-(2,4,6-trifluorophenyl)pyridine-2 obtained in step 1 177 mg of Dess-Martin reagent (1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one) was added to 4 ml of a dichloromethane solution of 176 mg of (1H)-one. The mixture was added and stirred at room temperature. After 1 hour and 5.5 hours, 177 mg of Dess-Martin reagent was added, respectively, and the mixture was stirred at room temperature for 105 minutes. A saturated aqueous sodium hydrogencarbonate solution 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 filtrate under reduced pressure, the resulting residue was purified by silica gel column chromatography. 94 mg of the title compound was obtained as a white solid.

４－ブロモ－３－（５－クロロ－１－エチル－６－オキソ－２－（２，４，６－トリフルオロフェニル）－１，６－ジヒドロピリジン－３－イル）イソキサゾール－５－カルバルデヒド ６８ｍｇのジクロロメタン溶液 ３ｍｌに、（ジエチルアミノ）サルファートリフルオリド ３９μｌを氷冷下で加えて、１０分間撹拌した後、室温で１００分間撹拌した。反応混合物に１規定塩酸と酢酸エチルを加えて分液した後に、得られた有機層を飽和食塩水で洗浄し、硫酸ナトリウムで乾燥した。濾液を減圧下にて溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が４５ｍｇの白色アモルファスとして得られた。[Synthesis Example 15]
5-(4-bromo-5-(difluoromethyl)isoxazol-3-yl)-3-chloro-1-ethyl-6-(2,4,6-trifluorophenyl)pyridin-2(1H)-one Synthesis (compound number: B-023)

4-bromo-3-(5-chloro-1-ethyl-6-oxo-2-(2,4,6-trifluorophenyl)-1,6-dihydropyridin-3-yl)isoxazole-5-carbaldehyde 68 mg (Diethylamino)sulfur trifluoride (39 μl) was added to 3 ml of a dichloromethane solution of (diethylamino)sulfur trifluoride under ice-cooling, stirred for 10 minutes, and then stirred at room temperature for 100 minutes. 1N Hydrochloric acid and ethyl acetate were added to the reaction mixture to separate the layers, and the obtained organic layer was washed with saturated brine and dried over sodium sulfate. After evaporating the filtrate under reduced pressure, the resulting residue was purified by silica gel column chromatography. 45 mg of the title compound was obtained as a white amorphous.

５－クロロ－１－エチル－６－オキソ－２－（２，４，６－トリフルオロフェニル）－１，６－ジヒドロピリジン－３－カルバルデヒド オキシム ３２５ｍｇとＮ－クロロスクシンイミド １９７ｍｇを含むＴＨＦ溶液 ６ｍｌを５０℃で４５分間撹拌した。室温まで冷却した後に、クロトンアルデヒド ４０５μｌとトリエチルアミン １５２μｌを加えて、室温で２時間撹拌した。反応混合物に飽和炭酸水素ナトリウム水溶液と酢酸エチルを加えて分液した後に、得られた有機層を飽和食塩水で洗浄し、硫酸ナトリウムで乾燥した。濾液を減圧下にて溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が１８４ｍｇの黄色アモルファスとして得られた。[Synthesis Example 16]
3-(5-chloro-1-ethyl-6-oxo-2-(2,4,6-trifluorophenyl)-1,6-dihydropyridin-3-yl)-5-methylisoxazole-4-carba Synthesis of rudehyde (compound number: B-027)

6 ml of THF solution containing 325 mg of 5-chloro-1-ethyl-6-oxo-2-(2,4,6-trifluorophenyl)-1,6-dihydropyridine-3-carbaldehyde oxime and 197 mg of N-chlorosuccinimide Stir at 50° C. for 45 minutes. After cooling to room temperature, 405 μl of crotonaldehyde and 152 μl of triethylamine were added and stirred at room temperature for 2 hours. A saturated aqueous solution of sodium hydrogencarbonate and ethyl acetate were added to the reaction mixture and the mixture was separated, and then the resulting organic layer was washed with saturated brine and dried over sodium sulfate. After evaporating the filtrate under reduced pressure, the resulting residue was purified by silica gel column chromatography. 184 mg of the title compound were obtained as a yellow amorphous.

３－（５－クロロ－１－エチル－６－オキソ－２－（２，４，６－トリフルオロフェニル）－１，６－ジヒドロピリジン－３－イル）－５－メチルイソキサゾール－４－カルバルデヒド ４４ｍｇ、Ｏ－メチルヒドロキシルアミン塩酸塩 １２ｍｇとピリジン １２μｌを含むエタノール溶液 ３ｍｌを室温で７５分間撹拌した。反応混合物に１規定塩酸と酢酸エチルを加えて分液した後に、得られた有機層を飽和食塩水で洗浄し、硫酸ナトリウムで乾燥した。濾液を減圧下にて溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が２８ｍｇの白色アモルファスとして得られた。[Synthesis Example 17]
3-(5-chloro-1-ethyl-6-oxo-2-(2,4,6-trifluorophenyl)-1,6-dihydropyridin-3-yl)-5-methylisoxazole-4-carba Synthesis of rudehyde O-methyl oxime (Compound No.: B-032)

3-(5-chloro-1-ethyl-6-oxo-2-(2,4,6-trifluorophenyl)-1,6-dihydropyridin-3-yl)-5-methylisoxazole-4-carba 3 ml of an ethanol solution containing 44 mg of rudehyde, 12 mg of O-methylhydroxylamine hydrochloride and 12 μl of pyridine was stirred at room temperature for 75 minutes. 1N Hydrochloric acid and ethyl acetate were added to the reaction mixture and the layers were separated, and the resulting organic layer was washed with saturated brine and dried over sodium sulfate. After evaporating the filtrate under reduced pressure, the resulting residue was purified by silica gel column chromatography. 28 mg of the title compound was obtained as a white amorphous.

３－（５－クロロ－１－エチル－６－オキソ－２－（２，４，６－トリフルオロフェニル）－１，６－ジヒドロピリジン－３－イル）－５－メチルイソキサゾール－４－カルバルデヒド ７１ｍｇ、（１－ジアゾ－２－オキソプロピル）ホスホン酸ジメチル ３２μｌと炭酸カリウム ３７ｍｇを含むメタノール溶液 ３ｍｌを室温で６５分間撹拌した。さらに、（１－ジアゾ－２－オキソプロピル）ホスホン酸ジメチル １１μｌを追加して、室温で３０分間撹拌した。反応混合物に飽和塩化アンモニウム水溶液と酢酸エチルを加えて分液した後に、得られた有機層を飽和食塩水で洗浄し、硫酸ナトリウムで乾燥した。減圧下で溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が２５ｍｇの白色固体として得られた。[Synthesis Example 18]
Synthesis of 3-chloro-1-ethyl-5-(4-ethynyl-5-methylisoxazol-3-yl)-6-(2,4,6-trifluorophenyl)pyridin-2(1H)-one (Compound number: B-033)

3-(5-chloro-1-ethyl-6-oxo-2-(2,4,6-trifluorophenyl)-1,6-dihydropyridin-3-yl)-5-methylisoxazole-4-carba 3 ml of a methanol solution containing 71 mg of rudehyde, 32 μl of dimethyl (1-diazo-2-oxopropyl)phosphonate and 37 mg of potassium carbonate was stirred at room temperature for 65 minutes. Further, 11 μl of dimethyl (1-diazo-2-oxopropyl)phosphonate was added, and the mixture was stirred at room temperature for 30 minutes. A saturated aqueous ammonium chloride solution and ethyl acetate were added to the reaction mixture and the mixture was separated, and the obtained organic layer was washed with saturated brine and dried over sodium sulfate. After evaporating the solvent under reduced pressure, the obtained residue was purified by silica gel column chromatography. 25 mg of the title compound was obtained as a white solid.

５－クロロ－１－エチル－６－オキソ－２－（２，４，６－トリフルオロフェニル）－１，６－ジヒドロピリジン－３－カルバルデヒド オキシム ２２７ｍｇとＮ－クロロスクシンイミド １３７ｍｇを含むＴＨＦ溶液 ５ｍｌを５０℃で５０分間撹拌した。室温まで冷却した後に、アセチルアセトン ３５１μｌとトリエチルアミン １０６μｌを加えて、室温で５時間撹拌した。反応混合物に飽和炭酸水素ナトリウム水溶液と酢酸エチルを加えて分液した後に、得られた有機層を飽和食塩水で洗浄し、硫酸ナトリウムで乾燥した。濾液を減圧下にて溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が１６４ｍｇの白色アモルファスとして得られた。[Synthesis Example 19]
Synthesis of 5-(4-acetyl-5-methylisoxazol-3-yl)-3-chloro-1-ethyl-6-(2,4,6-trifluorophenyl)pyridin-2(1H)-one (Compound number: B-035)

5-chloro-1-ethyl-6-oxo-2-(2,4,6-trifluorophenyl)-1,6-dihydropyridine-3-carbaldehyde oxime 227mg and N-chlorosuccinimide 137mg of THF solution 5ml Stir at 50° C. for 50 minutes. After cooling to room temperature, 351 μl of acetylacetone and 106 μl of triethylamine were added and stirred at room temperature for 5 hours. A saturated aqueous solution of sodium hydrogencarbonate and ethyl acetate were added to the reaction mixture and the mixture was separated, and then the resulting organic layer was washed with saturated brine and dried over sodium sulfate. After evaporating the filtrate under reduced pressure, the resulting residue was purified by silica gel column chromatography. The title compound was obtained as 164 mg of white amorphous.

５－（４－アセチル－５－メチルイソキサゾール－３－イル）－３－クロロ－１－エチル－６－（２，４，６－トリフルオロフェニル）ピリジン－２（１Ｈ）－オン １３７ｍｇのメタノール溶液 ３ｍｌに、水素化ホウ素ナトリウム ３８ｍｇを氷冷下で加えて、２０分間撹拌した。反応混合物に飽和塩化アンモニウム水溶液と酢酸エチルを加えて分液した後に、得られた有機層を飽和食塩水で洗浄し、硫酸ナトリウムで乾燥した。減圧下で溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が１１６ｍｇの白色アモルファスとして得られた。[Synthesis Example 20]
3-chloro-1-ethyl-5-(4-(1-hydroxyethyl)-5-methylisoxazol-3-yl)-6-(2,4,6-trifluorophenyl)pyridine-2(1H )-one synthesis (compound number: B-037)

5-(4-acetyl-5-methylisoxazol-3-yl)-3-chloro-1-ethyl-6-(2,4,6-trifluorophenyl)pyridin-2(1H)-one 137 mg 38 mg of sodium borohydride was added to 3 ml of the methanol solution under ice-cooling, and the mixture was stirred for 20 minutes. A saturated aqueous ammonium chloride solution and ethyl acetate were added to the reaction mixture and the mixture was separated, and the obtained organic layer was washed with saturated brine and dried over sodium sulfate. After evaporating the solvent under reduced pressure, the obtained residue was purified by silica gel column chromatography. 116 mg of the title compound was obtained as a white amorphous.

３－クロロ－１－エチル－５－（４－（１－ヒドロキシエチル）－５－メチルイソキサゾール－３－イル）－６－（２，４，６－トリフルオロフェニル）ピリジン－２（１Ｈ）－オン４１ｍｇとｐ－トルエンスルホン酸一水和物 １７ｍｇを含むトルエン溶液 ３ｍｌを１２０℃で３０分間撹拌した。室温まで冷却した後に、反応混合物に飽和炭酸水素ナトリウム水溶液と酢酸エチルを加えて分液した。得られた有機層を飽和食塩水で洗浄し、硫酸ナトリウムで乾燥した。濾液を減圧下にて溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が３６ｍｇの淡黄色ガム状物質として得られた。[Synthesis Example 21]
Synthesis of 3-chloro-1-ethyl-5-(5-methyl-4-vinylisoxazol-3-yl)-6-(2,4,6-trifluorophenyl)pyridin-2(1H)-one (Compound number: B-038)

3-chloro-1-ethyl-5-(4-(1-hydroxyethyl)-5-methylisoxazol-3-yl)-6-(2,4,6-trifluorophenyl)pyridine-2(1H 3 ml of a toluene solution containing 41 mg of )-one and 17 mg of p-toluenesulfonic acid monohydrate was stirred at 120° C. for 30 minutes. After cooling to room temperature, saturated aqueous sodium hydrogencarbonate solution and ethyl acetate were added to the reaction mixture to separate the layers. The obtained organic layer was washed with saturated saline and dried with sodium sulfate. After evaporating the filtrate under reduced pressure, the resulting residue was purified by silica gel column chromatography. 36 mg of the title compound was obtained as a pale yellow gum.

５－クロロ－１－エチル－６－オキソ－２－（２，４，６－トリフルオロフェニル）－１，６－ジヒドロピリジン－３－カルバルデヒド オキシム １５２ｍｇとＮ－クロロスクシンイミド ９２ｍｇを含むＴＨＦ溶液 ３ｍｌを５０℃で４５分間撹拌した。室温まで冷却した後に、１５重量％のイソブテンのＴＨＦ溶液 ４．１４ｍｌとトリエチルアミン ７１μｌを加えて、室温で１４０分間撹拌した。反応混合物に飽和炭酸水素ナトリウム水溶液と酢酸エチルを加えて分液した後に、得られた有機層を飽和食塩水で洗浄し、硫酸ナトリウムで乾燥した。濾液を減圧下にて溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が１４３ｍｇの淡黄色固体として得られた。[Synthesis Example 22]
3-chloro-5-(5,5-dimethyl-4,5-dihydroisoxazol-3-yl)-1-ethyl-6-(2,4,6-trifluorophenyl)pyridine-2(1H) -Synthesis of one (Compound No.: C-003)

3 ml of THF solution containing 5-chloro-1-ethyl-6-oxo-2-(2,4,6-trifluorophenyl)-1,6-dihydropyridine-3-carbaldehyde oxime 152 mg and N-chlorosuccinimide 92 mg Stir at 50° C. for 45 minutes. After cooling to room temperature, 4.14 ml of a 15% by weight isobutene solution in THF and 71 μl of triethylamine were added and stirred at room temperature for 140 minutes. A saturated aqueous solution of sodium hydrogencarbonate and ethyl acetate were added to the reaction mixture and the mixture was separated, and then the resulting organic layer was washed with saturated brine and dried over sodium sulfate. After evaporating the filtrate under reduced pressure, the resulting residue was purified by silica gel column chromatography. The title compound was obtained as 143 mg of pale yellow solid.

３－クロロ－５－（５，５－ジメチル－４，５－ジヒドロイソキサゾール－３－イル）－１－エチル－６－（２，４，６－トリフルオロフェニル）ピリジン－２（１Ｈ）－オン １１５ｍｇ、Ｎ－ブロモスクシンイミド ８０ｍｇとアゾビスイソブチロニトリル １０ｍｇを含む四塩化炭素溶液 ３ｍｌを９０℃で１．５時間撹拌した。室温まで冷却した後に、反応混合物にチオ硫酸ナトリウム水溶液と酢酸エチルを加えて分液した。得られた有機層を飽和食塩水で洗浄し、硫酸ナトリウムで乾燥した。濾液を減圧下にて溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が５１ｍｇの白色アモルファスとして得られた。[Synthesis Example 23]
5-(4-bromo-5,5-dimethyl-4,5-dihydroisoxazol-3-yl)3-chloro-1-ethyl-6-(2,4,6-trifluorophenyl)pyridine-2 Synthesis of (1H)-one (Compound No.: C-004)

3-chloro-5-(5,5-dimethyl-4,5-dihydroisoxazol-3-yl)-1-ethyl-6-(2,4,6-trifluorophenyl)pyridine-2(1H) 3 ml of a carbon tetrachloride solution containing 115 mg of -one, 80 mg of N-bromosuccinimide and 10 mg of azobisisobutyronitrile was stirred at 90° C. for 1.5 hours. After cooling to room temperature, an aqueous sodium thiosulfate solution and ethyl acetate were added to the reaction mixture to separate the layers. The obtained organic layer was washed with saturated saline and dried with sodium sulfate. After evaporating the filtrate under reduced pressure, the resulting residue was purified by silica gel column chromatography. 51 mg of the title compound was obtained as a white amorphous.

５－クロロ－１－エチル－Ｎ－ヒドロキシ－６－オキソ－２－（２，４，６－トリフルオロフェニル）－１，６－ジヒドロピリジン－３－カルビミドイル クロリド １１０ｍｇと２－（トリメチルシリル）フェニルトリフラート ２１９μｌを含むＴＨＦ溶液 ２ｍｌに、テトラブチルアンモニウムフルオリドのＴＨＦ溶液（１．０ｍｏｌ／Ｌ） １．０５ｍｌを加えて、室温で１０分間撹拌した。さらに、テトラブチルアンモニウムフルオリドのＴＨＦ溶液（１．０ｍｏｌ／Ｌ） ３０１μｌを追加して、室温で１０分間撹拌した。反応混合物に飽和塩化アンモニウム水溶液と酢酸エチルを加えて分液した後に、得られた有機層を飽和食塩水で洗浄し、硫酸ナトリウムで乾燥した。減圧下で溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が５１ｍｇの白色アモルファスとして得られた。[Synthesis Example 24]
Synthesis of 5-(benzo[d]isoxazol-3-yl)-3-chloro-1-ethyl-6-(2,4,6-trifluorophenyl)pyridin-2(1H)-one (compound number: D -001)

5-chloro-1-ethyl-N-hydroxy-6-oxo-2-(2,4,6-trifluorophenyl)-1,6-dihydropyridine-3-carbimidoyl chloride 110 mg and 2-(trimethylsilyl)phenyl triflate 219 μl 1.05 ml of a THF solution of tetrabutylammonium fluoride (1.0 mol/L) was added to 2 ml of a THF solution containing and stirred at room temperature for 10 minutes. Furthermore, 301 μl of a THF solution (1.0 mol/L) of tetrabutylammonium fluoride was added, and the mixture was stirred at room temperature for 10 minutes. A saturated aqueous ammonium chloride solution and ethyl acetate were added to the reaction mixture and the mixture was separated, and the obtained organic layer was washed with saturated brine and dried over sodium sulfate. After evaporating the solvent under reduced pressure, the obtained residue was purified by silica gel column chromatography. 51 mg of the title compound was obtained as a white amorphous.

５－クロロ－１－エチル－２－（４－フルオロフェニル）－６－オキソ－１，６－ジヒドロピリジン－３－カルボアルデヒド ３１４ｍｇ、ヒドロキシルアミン塩酸塩 １０１ｍｇとピリジン １１８μｌを含むエタノール溶液 ５ｍｌを室温で１５分間撹拌した。反応混合物に１規定塩酸と酢酸エチルを加えて分液した後に、得られた有機層を飽和食塩水で洗浄し、硫酸ナトリウムで乾燥した。減圧下で溶媒留去した後に、表題の化合物を含む３５３ｍｇの黄色アモルファスが得られた。これ以上精製することなく、次の反応に使用した。[Synthesis Example 25]
Step 1: Synthesis of 5-chloro-1-ethyl-2-(4-fluorophenyl)-6-oxo-1,6-dihydropyridine-3-carbaldehyde oxime

5-chloro-1-ethyl-2-(4-fluorophenyl)-6-oxo-1,6-dihydropyridine-3-carbaldehyde 314 mg, hydroxylamine hydrochloride 101 mg and pyridine 118 μl 5 ml of an ethanol solution containing 15 ml at room temperature. Stir for a minute. 1N Hydrochloric acid and ethyl acetate were added to the reaction mixture and the layers were separated, and the resulting organic layer was washed with saturated brine and dried over sodium sulfate. After evaporating the solvent under reduced pressure, 353 mg of a yellow amorphous was obtained containing the title compound. Used for next reaction without further purification.

ステップ１で得られた５－クロロ－１－エチル－２－（４－フルオロフェニル）－６－オキソ－１，６－ジヒドロピリジン－３－カルボアルデヒドオキシム ２３２ｍｇとＮ－クロロスクシンイミド １５８ｍｇを含むＴＨＦ溶液 ４．５ｍｌを５０℃で８０分間撹拌した。さらにＮ－クロロスクシンイミド １０５ｍｇを追加して、５０℃で１５分間撹拌した。室温まで冷却した後に、エチルビニルエーテル ３７８μｌとトリエチルアミン １２２μｌを加えて、室温で１５分間撹拌した。反応混合物に飽和炭酸水素ナトリウム水溶液と酢酸エチルを加えて分液した後に、得られた有機層を飽和食塩水で洗浄し、硫酸ナトリウムで乾燥した。濾液を減圧下にて溶媒留去し、残渣を得た。得られた残渣とｐ－トルエンスルホン酸一水和物 １３６ｍｇを含むトルエン溶液 ４．５ｍｌを還流下で３５分間撹拌した。室温まで冷却した後に、反応混合物に飽和炭酸水素ナトリウム水溶液と酢酸エチルを加えて分液した。得られた有機層を飽和食塩水で洗浄し、硫酸ナトリウムで乾燥した。濾液を減圧下にて溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が１１２ｍｇの白色固体として得られた。 ¹ H-NMR (CDCl ₃ ) δ: 8.10 (1H, s), 7.28-7.24 (5H, m), 7.04 (1H, s), 3.85 (2H, q, J = 7.0 Hz), 1.14 (3H, t, J = 7.0 Hz).
Step 2: Synthesis of 3-chloro-1-ethyl-6-(4-fluorophenyl)-5-(isoxazol-3-yl)pyridin-2(1H)-one (Compound No.: B-012)

THF solution containing 232 mg of 5-chloro-1-ethyl-2-(4-fluorophenyl)-6-oxo-1,6-dihydropyridine-3-carbaldehyde oxime obtained in Step 1 and 158 mg of N-chlorosuccinimide 4 .5 ml was stirred at 50° C. for 80 minutes. Further, 105 mg of N-chlorosuccinimide was added, and the mixture was stirred at 50°C for 15 minutes. After cooling to room temperature, 378 μl of ethyl vinyl ether and 122 μl of triethylamine were added and stirred at room temperature for 15 minutes. A saturated aqueous solution of sodium hydrogencarbonate and ethyl acetate were added to the reaction mixture and the mixture was separated, and then the resulting organic layer was washed with saturated brine and dried over sodium sulfate. The filtrate was evaporated under reduced pressure to give a residue. A toluene solution (4.5 ml) containing the resulting residue and p-toluenesulfonic acid monohydrate (136 mg) was stirred under reflux for 35 minutes. After cooling to room temperature, saturated aqueous sodium hydrogencarbonate solution and ethyl acetate were added to the reaction mixture to separate the layers. The obtained organic layer was washed with saturated saline and dried with sodium sulfate. After evaporating the filtrate under reduced pressure, the resulting residue was purified by silica gel column chromatography. 112 mg of the title compound was obtained as a white solid.

３－クロロ－１－エチル－６－（４－フルオロフェニル）－５－（イソキサゾール－３－イル）ピリジン－２（１Ｈ）－オン ９１ｍｇと臭素 ４３８μｌを含む酢酸溶液 ２．５ｍｌを１２０℃で撹拌した。１３時間後、２２時間後に、臭素 ４３８μｌをそれぞれ追加した後に、１２０℃で４時間撹拌した。室温まで冷却した後に、反応混合物に飽和炭酸水素ナトリウム水溶液と酢酸エチルを加えて分液した。得られた有機層をチオ硫酸ナトリウム水溶液と飽和食塩水で順次洗浄し、硫酸ナトリウムで乾燥した。濾液を減圧下にて溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が４０ｍｇの白色固体として得られた。[Synthesis Example 26]
Synthesis of 5-(4-bromoisoxazol-3-yl)-3-chloro-1-ethyl-6-(4-fluorophenyl)pyridin-2(1H)-one (Compound No.: B-015)

2.5 ml of an acetic acid solution containing 91 mg of 3-chloro-1-ethyl-6-(4-fluorophenyl)-5-(isoxazol-3-yl)pyridin-2(1H)-one and 438 μl of bromine was stirred at 120°C. did. After 13 hours and 22 hours, 438 μl of bromine was added, respectively, and the mixture was stirred at 120° C. for 4 hours. After cooling to room temperature, saturated aqueous sodium hydrogencarbonate solution 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 filtrate under reduced pressure, the resulting residue was purified by silica gel column chromatography. 40 mg of the title compound was obtained as a white solid.

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 1]

Step 1: Synthesis of 1-(2,6-difluorophenyl)-N-phenylpropane-1-imine A dichloromethane solution containing 23.91 g of titanium tetrachloride in 100 ml of a dichloromethane solution containing 11.74 g of aniline and 17.01 g of triethylamine. 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 evaporation under reduced pressure, 21.10 g of a dark green oil containing the title compound was obtained. Used for 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 dioxane solution containing 21.10 g of phenylpropane-1-imine and 12.33 g of aluminum chloride, and the mixture was stirred at 90° C. for 3 hours. After distilling off the solvent under reduced pressure to about half the amount of the reaction mixture, 1N hydrochloric acid and ethyl acetate were added to separate the layers. The obtained organic layer was washed with saturated saline and dried with sodium sulfate. After evaporating the solvent under reduced pressure, the obtained residue was purified by silica gel column chromatography. The resulting solid was washed with isopropyl ether to give 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).

６－（２，６－ジフルオロフェニル）－５－メチル－３，４－ジヒドロピリジン－２（１Ｈ）－オン １２．４０ｇ、炭酸セシウム ５４．３０ｇおよびヨウ化エチル ２５．９９ｇを含むＤＭＦ溶液 １２０ｍｌを５０℃で３．５時間撹拌した。次いで炭酸セシウム ２７．１５ｇおよびヨウ化エチル １３．０１ｇを追加した後に、５０℃で２時間、さらに６０℃で１．５時間撹拌した。室温まで冷却後、該反応混合物を濾過することにより不溶物を除去した。濾液を減圧下にて溶媒留去した後に、酢酸エチルと水を加えて分液した。得られた有機層をチオ硫酸ナトリウム水溶液および飽和食塩水で順次洗浄し、硫酸ナトリウムで乾燥した。減圧下で溶媒留去した後に、得られた固体をイソプロピルエーテルで洗浄した。表題の化合物が１１．９８ｇの白色固体として得られた。[Reference example 2]
Synthesis of 6-(2,6-difluorophenyl)-1-ethyl-5-methyl-3,4-dihydropyridin-2(1H)-one

120 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 was C. for 3.5 hours. After adding 27.15 g of cesium carbonate and 13.01 g of ethyl iodide, the mixture was stirred 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 insolubles. After evaporating the solvent from the filtrate under reduced pressure, ethyl acetate and water were added 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 solid obtained was washed with isopropyl ether. 11.98 g of the title compound was obtained as 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).

６－（２，６－ジフルオロフェニル）－１－エチル－５－メチル－３，４－ジヒドロピリジン－２（１Ｈ）－オン １１．９８ｇと２，３－ジクロロ－５，６－ジシアノ－ｐ－ベンゾキノン ２１．６５ｇを含むトルエン溶液 １７０ｍｌを１２０℃で１．５時間撹拌した。室温まで冷却した後に、反応混合物を濾過することにより不溶物を除去した。濾液を減圧下で溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。得られた固体をイソプロピルエーテルで洗浄し、表題の化合物が９．３４ｇの淡黄色固体として得られた。[Reference example 3]
Synthesis of 6-(2,6-difluorophenyl)-1-ethyl-5-methylpyridin-2(1H)-one

6-(2,6-difluorophenyl)-1-ethyl-5-methyl-3,4-dihydropyridin-2(1H)-one 11.98 g 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 insolubles. After evaporating the filtrate under reduced pressure, the resulting residue was purified by silica gel column chromatography. The resulting solid was washed with isopropyl ether to give 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).

６－（２，６－ジフルオロフェニル）－１－エチル－５－メチルピリジン－２（１Ｈ）－オン １１．３６ｇとＮ－クロロスクシンイミド ６．６９ｇを含むＤＭＦ溶液 １１０ｍｌを７０℃で５０分間撹拌した。室温まで冷却した後に、反応混合物を減圧下で溶媒留去した。これに酢酸エチルと水を加えて分液した後に、得られた有機層をチオ硫酸ナトリウム水溶液および飽和食塩水で順次洗浄し、硫酸ナトリウムで乾燥した。減圧下で溶媒留去した後に、得られた固体をイソプロピルエーテルで洗浄した。表題の化合物が１１．４１ｇの白色固体として得られた。[Reference Example 4]
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. Ethyl acetate and water were added to the mixture, and the mixture was separated. 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 solid obtained was washed with isopropyl ether. 11.41 g of the title compound was obtained as a white solid.

¹ H-NMR (CDCl ₃ ) 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).

３－クロロ－６－（２，６－ジフルオロフェニル）－１－エチル－５－メチルピリジン－２（１Ｈ）－オン １２．６５ｇを含むクロロベンゼン溶液 ２３０ｍｌに、Ｎ－ブロモスクシンイミド １６．６７ｇとアゾビスイソブチロニトリル ３６６ｍｇを加えて、１１０℃で５０分間撹拌した。室温まで冷却した後に、反応混合物に水とジクロロメタンを加えて分液した。得られた有機層をチオ硫酸ナトリウム水溶液で洗浄し、硫酸ナトリウムで乾燥した。減圧下で溶媒留去した後に、得られた固体をイソプロピルエーテルで洗浄した。表題の化合物が１６．８８ｇの淡褐色固体として得られた。[Reference Example 5]
Synthesis of 3-chloro-5-(dibromomethyl)-6-(2,6-difluorophenyl)-1-ethylpyridin-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 resulting organic layer was washed with an aqueous sodium thiosulfate solution and dried over sodium sulfate. After evaporating the solvent under reduced pressure, the solid obtained was washed with isopropyl ether. The title compound was obtained as 16.88 g of a pale brown solid.

¹ H-NMR (CDCl ₃ ) 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).

３－クロロ－５－（ジブロモメチル）－６－（２，６－ジフルオロフェニル）－１－エチルピリジン－２（１Ｈ）－オン １８．９５ｇを含むアセトニトリル ３８０ｍｌに、硝酸銀 ２１．８７ｇを含む水溶液 １９０ｍｌを加えて室温で１５分撹拌した。得られた反応混合物を濾過することにより不溶物を除去した。濾液を減圧下にて溶媒留去した後に、水と酢酸エチルを加えて分液した。得られた有機層を１規定塩酸と飽和食塩水で洗浄し、硫酸ナトリウムで乾燥した。減圧下で溶媒留去した後に、得られた固体をイソプロピルエーテルで洗浄した。表題の化合物が１１．３７ｇの淡黄色固体として得られた。[Reference Example 6]
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 insoluble matter was removed by filtering the obtained reaction mixture. After evaporating the solvent from 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 solid obtained was washed with isopropyl ether. 11.37 g of the title compound was obtained as 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).

５－クロロ－２－（２，６－ジフルオロフェニル）－１－エチル－６－オキソ－１，６－ジヒドロピリジン－３－カルボアルデヒド ０．８０ｇを含むＴＨＦ溶液 ２０ｍｌに、メチルマグネシウムブロミドのＴＨＦ溶液（１．０ｍｏｌ／Ｌ） ８．００ｍｌを氷冷下で滴下して２時間撹拌した。該反応混合物に飽和塩化アンモニウム水溶液と酢酸エチルを加えて分液した後に、得られた有機層を飽和食塩水で洗浄し、硫酸ナトリウムで乾燥した。減圧下で溶媒留去した後に、表題の化合物が０．８１ｇの白色固体として得られた。これ以上精製することなく、次の反応に使用した。[Reference Example 7]
Synthesis of 3-chloro-6-(2,6-difluorophenyl)-1-ethyl-5-(1-hydroxyethyl)pyridin-2(1H)-one

To 20 ml of a THF solution containing 0.80 g of 5-chloro-2-(2,6-difluorophenyl)-1-ethyl-6-oxo-1,6-dihydropyridine-3-carbaldehyde, a THF solution of methylmagnesium bromide ( 1.0 mol/L) (8.00 ml) was added dropwise under ice-cooling, and the mixture was stirred for 2 hours. A saturated aqueous solution of ammonium chloride and ethyl acetate were added to the reaction mixture and the layers were separated, and the resulting organic layer was washed with saturated brine and dried over sodium sulfate. After evaporation of the solvent under reduced pressure, 0.81 g of the title compound was obtained as a white solid. Used for next reaction without further purification.

¹ H-NMR (CDCl ₃ ) δ: 7.86 (1H, s), 7.56-7.54 (1H, m), 7.13-7.08 (2H, m), 4.25-4 .23 (1H, m), 3.89-3.86 (1H, m), 3.81-3.78 (1H, m), 1.65 (1H, d, J = 2.8 Hz), 1.29 (3H, d, J = 6.4 Hz), 1.12 (3H, t, J = 7.0 Hz).

３－クロロ－６－（２，６－ジフルオロフェニル）－１－エチル－５－（１－ヒドロキシエチル）ピリジン－２（１Ｈ）－オン ０．８１ｇとジメチルスルホキシド ３ｍｌを含むジクロロメタン溶液 ９ｍｌに、トリエチルアミン １．８０ｍｌとピリジン－三酸化硫黄コンプレックス １．６４ｇを氷冷下で加えて２時間撹拌した。該反応混合物に１規定塩酸と酢酸エチルを加えて分液した後に、得られた有機層を飽和炭酸水素ナトリウム水溶液と飽和食塩水で順次洗浄し、硫酸ナトリウムで乾燥した。減圧下で溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が０．７４ｇの淡黄色固体として得られた。[Reference Example 8]
Synthesis of 5-acetyl-3-chloro-6-(2,6-difluorophenyl)-1-ethylpyridin-2(1H)-one

In 9 ml of a dichloromethane solution containing 0.81 g of 3-chloro-6-(2,6-difluorophenyl)-1-ethyl-5-(1-hydroxyethyl)pyridin-2(1H)-one and 3 ml of dimethylsulfoxide, triethylamine 1.80 ml and 1.64 g of pyridine-sulfur trioxide complex were added under ice-cooling and stirred for 2 hours. 1N Hydrochloric acid and ethyl acetate were added to the reaction mixture and the layers were separated, and the resulting organic layer was washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated brine and dried over sodium sulfate. After evaporating the solvent under reduced pressure, the obtained residue was purified by silica gel column chromatography. 0.74 g of the title compound was obtained as a pale yellow solid.

ステップ１：５－（４－フルオロフェニル）－４－メチル－５－オキソペンタン酸エチルの合成
４－フルオロプロピオフェノン ２５．０ｇを含むＴＨＦ溶液 ２５０ｍｌに、カリウム ｔ－ブトキシド ３．６９ｇとアクリル酸エチル １７．２７ｇを加えて、氷冷下で３時間撹拌した。これに飽和塩化アンモニウム水溶液と酢酸エチルを加えて分液した後に、得られた有機層を飽和食塩水にて洗浄し、硫酸ナトリウムで乾燥した。減圧下にて溶媒留去し、表題の化合物が４１．５ｇの黄色油状物質として得られた。これ以上精製することなく次の反応に使用した。[Reference Example 9]

Step 1: Synthesis of ethyl 5-(4-fluorophenyl)-4-methyl-5-oxopentanoate To 250 ml of THF solution containing 25.0 g of 4-fluoropropiophenone, 3.69 g of potassium t-butoxide and acrylic acid were added. 17.27 g of ethyl was added and stirred for 3 hours under ice-cooling. A saturated aqueous ammonium chloride solution and ethyl acetate were added to the mixture, and the mixture was separated. The resulting organic layer was washed with saturated brine and dried over sodium sulfate. The solvent was distilled off under reduced pressure to obtain 41.5 g of the title compound as a yellow oil. Used for next reaction without further purification.

¹ H-NMR (CDCl ₃ ) δ: 8.01-8.00 (2H, m), 7.17-7.11 (2H, m), 4.11 (2H, q, J = 7.2 Hz ), 3.55-3.53 (1H, m), 2.42-2.27 (1H, m), 2.19-2.12 (1H, m), 1.78-1.74 (1H , m), 1.23 (3H, t, J = 7.2 Hz), 1.21 (3H, d, J = 7.0 Hz).
Step 2: Synthesis of 5-(4-fluorophenyl)-4-methyl-5-oxopentanoic acid Ethyl 5-(4-fluorophenyl)-4-methyl-5-oxopentanoate obtained in step 141. After adding 200 ml of THF and 100 ml of water to 5 g, 20.71 g of lithium hydroxide monohydrate was added and stirred at 60° C. for 3 hours. After cooling to room temperature, THF in the reaction mixture was distilled off under reduced pressure. Water and diethyl ether were added to the mixture to separate the layers, and 12 N hydrochloric acid and ethyl acetate were added to the resulting aqueous layer to separate the layers. The obtained organic layer was washed with saturated saline and dried with sodium sulfate. After evaporation of the solvent under reduced pressure, 34.0 g of the title compound was obtained as a brown oil.

¹ H-NMR (CDCl ₃ ) δ: 8.02-7.98 (2H, m), 7.16-7.13 (2H, m), 3.56-3.53 (1H, m), 2 .49-2.33 (2H, m), 2.18-2.15 (1H, m), 1.79-1.77 (1H, m), 1.22 (3H, d, J = 7. 0 Hz).

５－（４－フルオロフェニル）－４－メチル－５－オキソペンタン酸 ３４．０ｇと酢酸アンモニウム ２３３．７ｇを含む酢酸溶液 ３４０ｍｌを、９０℃で３時間撹拌した後に、さらに１２０℃で５時間撹拌した。室温まで冷却した後に、反応混合物に酢酸エチルと水を加えて分液した。得られた有機層を飽和食塩水にて洗浄し、硫酸ナトリウムで乾燥した。減圧下で溶媒留去を行った後に、ジイソプロピルエーテルにより析出物を洗浄した。得られた褐色固体 １７．８ｇは表題の化合物であった。[Reference Example 10]
Synthesis of 6-(4-fluorophenyl)-5-methyl-3,4-dihydropyridin-2(1H)-one

340 ml of an acetic acid solution containing 34.0 g of 5-(4-fluorophenyl)-4-methyl-5-oxopentanoic acid and 233.7 g of ammonium acetate was stirred at 90° C. for 3 hours, and then stirred at 120° C. for 5 hours. did. After cooling to room temperature, ethyl acetate and water were added to the reaction mixture to separate the layers. The obtained organic layer was washed with saturated saline and dried with sodium sulfate. After distilling off the solvent under reduced pressure, the precipitate was washed with diisopropyl ether. The resulting 17.8 g brown solid was the title compound.

¹ H-NMR (CDCl ₃ ) δ: 7.29-7.25 (2H, m), 7.11-7.06 (2H, m), 6.77 (1H, s), 2.58-2 .55 (2H, m), 2.43-2.41 (2H, m), 1.73 (3H, t, J = 0.9 Hz).

６－（４－フルオロフェニル）－５－メチル－３，４－ジヒドロピリジン－２（１Ｈ）－オン １７．３ｇを含むＤＭＦ溶液 １７３ｍｌに、ヨウ化エチル ２０．１７ｍｌと炭酸セシウム ８２．１６ｇを加えて、７０℃で３時間撹拌した後に、さらに９０℃で８時間撹拌した。室温まで冷却した後に、反応混合物に水と酢酸エチルを加えて分液した。得られた有機層を水および飽和食塩水で順次洗浄し、硫酸マグネシウムで乾燥した。減圧下で溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が８．１１ｇの淡黄色油状物質として得られた。[Reference Example 11]
Synthesis of 1-ethyl-6-(4-fluorophenyl)-5-methyl-3,4-dihydropyridin-2(1H)-one

To 173 ml of DMF solution containing 17.3 g of 6-(4-fluorophenyl)-5-methyl-3,4-dihydropyridin-2(1H)-one, 20.17 ml of ethyl iodide and 82.16 g of cesium carbonate were added. , 70°C for 3 hours, and then at 90°C for 8 hours. After cooling to room temperature, water and ethyl acetate were added to the reaction mixture to separate the layers. The resulting organic layer was washed with water and saturated brine in that order and dried over magnesium sulfate. After evaporating the solvent under reduced pressure, the obtained residue was purified by silica gel column chromatography. The title compound was obtained as 8.11 g of pale yellow oil.

¹ H-NMR (CDCl ₃ ) δ: 7.19-7.16 (2H, m), 7.12-7.07 (2H, m), 3.33 (2H, q, J = 7.0 Hz ), 2.59-2.54 (2H, m), 2.33-2.30 (2H, m), 1.60 (3H, s), 0.89 (3H, t, J = 7.0 Hz).

１－エチル－６－（４－フルオロフェニル）－５－メチル－３，４－ジヒドロピリジン－２（１Ｈ）－オン ８．１１ｇと２，３－ジクロロ－５，６－ジシアノ－ｐ－ベンゾキノン １５．７９ｇを含むトルエン溶液 １３０ｍｌを９０℃で４時間撹拌した。室温まで冷却した後に、反応混合物を濾過することにより不溶物を除去した。濾液を減圧下で溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が６．３０ｇの黄色固体物質として得られた。[Reference Example 12]
Synthesis of 1-ethyl-6-(4-fluorophenyl)-5-methylpyridin-2(1H)-one

1-ethyl-6-(4-fluorophenyl)-5-methyl-3,4-dihydropyridin-2(1H)-one 8.11 g and 2,3-dichloro-5,6-dicyano-p-benzoquinone 15. 130 ml of a toluene solution containing 79 g was stirred at 90° C. for 4 hours. After cooling to room temperature, the reaction mixture was filtered to remove insoluble matter. After evaporating the filtrate under reduced pressure, the obtained residue was purified by silica gel column chromatography. The title compound was obtained as 6.30 g of yellow solid material.

¹ H-NMR (CDCl ₃ ) δ: 7.25-7.18 (5H, m), 6.58 (1H, d, J = 9.3 Hz), 3.79 (2H, q, J = 7 .1 Hz), 1.73 (3H, s), 1.09 (3H, t, J = 7.1 Hz).

１－エチル－６－（４－フルオロフェニル）－５－メチルピリジン－２（１Ｈ）－オン ６．３０ｇとＮ－クロロスクシンイミド ４．００ｇを含むＤＭＦ溶液 ６３ｍｌを７０℃で３時間撹拌した。室温まで冷却した後に、反応混合物に酢酸エチルと水を加えて分液した。得られた有機層をチオ硫酸ナトリウム水溶液および飽和食塩水で順次洗浄し、硫酸ナトリウムで乾燥した。減圧下で溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が６．２５ｇの褐色固体として得られた。[Reference Example 13]
Synthesis of 3-chloro-1-ethyl-6-(4-fluorophenyl)-5-methylpyridin-2(1H)-one

63 ml of DMF solution containing 6.30 g of 1-ethyl-6-(4-fluorophenyl)-5-methylpyridin-2(1H)-one and 4.00 g of N-chlorosuccinimide was stirred at 70° C. for 3 hours. After cooling to room temperature, ethyl acetate and water 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 obtained residue was purified by silica gel column chromatography. 6.25 g of the title compound was obtained as a brown solid.

¹ H-NMR (CDCl ₃ ) δ: 7.47 (1H, s), 7.23-7.21 (4H, m), 3.84 (2H, q, J = 7.1 Hz), 75 (3H, s), 1.11 (3H, t, J = 7.1 Hz).

３－クロロ－１－エチル－６－（４－フルオロフェニル）－５－メチルピリジン－２（１Ｈ）－オン ５．１７ｇを含むクロロベンゼン溶液 １００ｍｌに、Ｎ－ブロモスクシンイミド ７．２５ｇとアゾビスイソブチロニトリル ３１８ｍｇを加えて、９０℃で４時間撹拌した。室温まで冷却した後に、反応混合物に水とジクロロメタンを加えて分液した。得られた有機層をチオ硫酸ナトリウム水溶液で洗浄し、硫酸ナトリウムで乾燥した。減圧下で溶媒留去した後に、得られた固体をイソプロピルエーテルで洗浄した。表題の化合物が７．３７ｇの褐色固体として得られた。[Reference Example 14]
Synthesis of 3-chloro-5-(dibromomethyl)-1-ethyl-6-(4-fluorophenyl)pyridin-2(1H)-one

7.25 g of N-bromosuccinimide and azobisisobutyl were added to 100 ml of a chlorobenzene solution containing 5.17 g of 3-chloro-1-ethyl-6-(4-fluorophenyl)-5-methylpyridin-2(1H)-one. 318 mg of lonitrile was added and stirred at 90° C. for 4 hours. After cooling to room temperature, water and dichloromethane were added to the reaction mixture to separate the layers. The resulting organic layer was washed with an aqueous sodium thiosulfate solution and dried over sodium sulfate. After evaporating the solvent under reduced pressure, the solid obtained was washed with isopropyl ether. The title compound was obtained as 7.37 g of brown solid.

¹ H-NMR (CDCl ₃ ) δ: 8.09 (1H, s), 7.35-7.29 (4H, m), 5.86 (1H, s), 3.78 (2H, q, J = 7.0 Hz), 1.11 (3H, t, J = 7.0 Hz).

３－クロロ－５－（ジブロモメチル）－１－エチル－６－（４－フルオロフェニル）ピリジン－２（１Ｈ）－オン ８．６７ｇを含むアセトニトリル １３０ｍｌに、硝酸銀 １０．４１ｇを含む水溶液 ６５ｍｌを加えて室温で３時間撹拌した。得られた反応混合物を濾過することにより不溶物を除去した。濾液を減圧下にて溶媒留去した後に、水と酢酸エチルを加えて分液した。得られた有機層を１規定塩酸と飽和食塩水で洗浄し、硫酸ナトリウムで乾燥した。減圧下で溶媒留去した後に、得られた固体をイソプロピルエーテルで洗浄した。表題の化合物が５．０１ｇの黄色固体として得られた。[Reference Example 15]
Synthesis of 5-chloro-1-ethyl-2-(4-fluorophenyl)-6-oxo-1,6-dihydropyridine-3-carbaldehyde

65 ml of an aqueous solution containing 10.41 g of silver nitrate was added to 130 ml of acetonitrile containing 8.67 g of 3-chloro-5-(dibromomethyl)-1-ethyl-6-(4-fluorophenyl)pyridin-2(1H)-one. and stirred at room temperature for 3 hours. The insoluble matter was removed by filtering the obtained reaction mixture. After evaporating the solvent from 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 solid obtained was washed with isopropyl ether. 5.01 g of the title compound was obtained as a yellow solid.

¹ H-NMR (CDCl ₃ ) δ: 9.09 (1H, s), 8.11 (1H, s), 7.40-7.39 (2H, m), 7.31-7.29 (2H , m), 3.90 (2H, q, J = 7.1 Hz), 1.18 (3H, t, J = 7.1 Hz).
Tables 4 to 7 show compounds synthesized according to the above examples, but the present invention is not limited to these.

In Table 4, compounds whose compound numbers start with A have the following structures. Moreover, ratio in Table 4 represents the isomer ratio.

In Table 5, compounds whose compound number starts with B represent formula (2).

In Table 6, compounds whose compound number starts with C represent formula (3).

In Table 7, compounds whose compound number starts with D represent formula (4).

Next, Tables 8-11 show their ¹ H-NMR data for the compounds listed in Tables 4-7.

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

[Test Example A] Rice blast Seeds of a test plant (rice variety: Kofu) were sown and cultivated until the second leaf developed. In the test, the compound of the present invention was dissolved in a dimethylsulfoxide-methanol mixed solution (volume ratio: 9/1) and diluted with well water to a concentration of 250 ppm to obtain a chemical solution. The resulting chemical solution was sprayed on the test plants (2.5 ml/pot). After the chemical solution had dried, the plants were spray-inoculated with a conidia suspension of 1 to 2×10 ⁵ conidia/ml of Magnaporthe grisea. After inoculation, the plants were left in a moist room at a room temperature of 20 to 23°C for about 24 hours to promote disease development. 6 to 10 days after inoculation, the degree of disease development was investigated to evaluate the effect of the drug solution.

[Test Example B] Gray mold of tomato Seeds of a test plant (tomato variety: Dai Fukuju) were sown and cultivated until 3 to 5 true leaves developed. In the test, the compound of the present invention was dissolved in a dimethylsulfoxide-methanol mixed solution (volume ratio: 9/1) and diluted with well water to a concentration of 250 ppm to obtain a chemical solution. The resulting chemical solution was sprayed on the test plants (2.5 ml/pot). After the chemical solution had dried, the plants were spray-inoculated with a conidia suspension of 4-8×10 ⁵ cells/ml of Botrytis cinerea. After inoculation, the plants were left in a moist room at a room temperature of 20 to 23°C for about 48 hours to promote disease development. 2 to 3 days after inoculation, the degree of disease development was investigated to evaluate the effect of the drug solution.

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

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

[Test Example E] Wheat leaf rust Seeds of a test plant (wheat variety: Norin No. 61) were sown and cultivated until the first leaves developed. In the test, the compound of the present invention was dissolved in a dimethylsulfoxide-methanol mixed solution (volume ratio: 9/1) and diluted with well water to a concentration of 250 ppm to obtain a chemical solution. The resulting chemical solution was sprayed on the test plants (2.5 ml/pot). After the chemical solution had dried, the plants were spray-inoculated with a uredospore suspension of 1-2×10 ⁵ cells/ml of Puccinia recondita. After inoculation, the plants were left in a moist room at a room temperature of 20 to 23°C for about 24 hours to promote disease development. 7 to 10 days after inoculation, the degree of disease onset was investigated, and the effect of the drug solution was evaluated.

[Test Example F] Late blight of tomato Seeds of a test plant (tomato variety: Dai Fukuju) were sown and cultivated until 3 to 5 true leaves developed. In the test, the compound of the present invention was dissolved in a dimethylsulfoxide-methanol mixed solution (volume ratio: 9/1) and diluted with well water to a concentration of 250 ppm to obtain a chemical solution. The resulting chemical solution was sprayed on the test plants (2.5 ml/pot). After the chemical solution had dried, the plants were spray-inoculated with a zoospore suspension of Phytophthora infestans at 4-8×10 ³ cells/ml. After inoculation, the plants were left in a moist room at a room temperature of 20°C for about 24 hours to promote disease development. 5 to 10 days after inoculation, the degree of disease development was investigated to evaluate the effect of the drug solution.

[Test Example G] Downy mildew of a test plant (grape variety: Neo Muscat) was sown and cultivated until 3 to 4 true leaves developed. In the test, the compound of the present invention was dissolved in a dimethylsulfoxide-methanol mixed solution (volume ratio: 9/1) and diluted with well water to a concentration of 250 ppm to obtain a chemical solution. The resulting chemical solution was sprayed on the test plants (2.5 ml/pot). After the chemical solution had dried, the plants were spray inoculated with a zoosporangial suspension of 1-2×10 ⁴ cells/ml of Plasmopara viticola. After inoculation, the plants were left in a moist room at a room temperature of 20°C for about 24 hours to promote disease development. 7 to 10 days after inoculation, the degree of disease development was investigated to evaluate the effect of the drug solution.

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

With regard to the degree of disease onset in the above test examples, the degree of disease onset in non-diseased plants was set to 0, and the degree of disease onset in plants not treated with chemicals was set to 3, and the degree of disease onset was evaluated in increments of 0.05. In addition, the preventive value was calculated according to the following formula from the degree of disease development.
<Control value>
Control value = 100 {1-(n/3)}
Tables 12 to 15 show the test results for n=symptomatic disease in each drug-treated plot. In the table, H indicates that the control value is greater than 50%, and L indicates that the control value is 50% or less.

Since the pyridone compound of the present invention is a novel compound and can control plant diseases, it is useful as an agricultural chemical, for example, an agricultural and horticultural pesticide, especially an agricultural and horticultural fungicide.

The disclosure of Japanese Patent Application No. 2017-115359 (filing date: June 12, 2017) is incorporated herein by reference in its entirety.

All publications, patent applications and technical standards mentioned herein are to the same extent as if each individual publication, patent application and technical standard were specifically and individually noted to be incorporated by reference. incorporated herein by reference.

Claims (7)

formula (1)

[In the formula, R is
hydroxyl group,
cyano group,
a C1-C6 alkyl group optionally substituted with a substituent A,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with a substituent A,
a C2-C6 alkenyl group optionally substituted with a substituent A,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted with a substituent A,
a C2-C6 haloalkynyl group,
a C1-C6 alkoxy group optionally substituted with a substituent A,
a C1-C6 haloalkoxy group,
a C3-C8 cycloalkoxy group optionally substituted with a substituent A,
a C2-C6 alkenyloxy group optionally substituted with a substituent A,
a C2-C6 haloalkenyloxy group,
a C3-C6 alkynyloxy group optionally substituted with a substituent A,
a C3-C6 haloalkynyloxy group,
or RaRbN- (wherein Ra and Rb are each independently a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, or a C3-C8 Alternatively, Ra and Rb together with the attached nitrogen atom form an aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl, homopiperidinyl, or azocanyl group). represent;
R2 is
hydrogen atom,
cyano group,
nitro group,
halogen atom,
a C1-C6 alkyl group optionally substituted with a substituent A,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with a substituent A,
a C2-C6 alkenyl group optionally substituted with a substituent A,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted with a substituent A,
a C2-C6 haloalkynyl group,
a C1-C6 alkoxy group optionally substituted with a substituent A,
a C1-C6 haloalkoxy group,
a C3-C8 cycloalkoxy group optionally substituted with a substituent A,
a C2-C6 alkenyloxy group optionally substituted with a substituent A,
a C2-C6 haloalkenyloxy group,
a C3-C6 alkynyloxy group optionally substituted with a substituent A,
a C3-C6 haloalkynyloxy group,
Rc-L- (wherein Rc represents a C1-C6 alkyl group or a C1 _- C6 haloalkyl group, and L represents S, SO, or SO2),
RaRbN- (wherein Ra and Rb are as defined above),
or RdC(=O)-(wherein Rd is a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, C1 represents a C6 alkoxy group, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group, or RaRbN- (wherein Ra and Rb are as defined above);
X represents an oxygen atom or a sulfur atom;
Y is
a phenyl group optionally substituted with 0 to 5 substituents with R3 (however, in the case of disubstituted or more R3, each is independent),
a pyridyl group optionally substituted with 0 to 4 substituents with R3 (provided that, in the case of two or more substituted R3, each is independent),
a pyridazinyl group optionally substituted by R3 with 0 to 3 substituents (provided that, in the case of two or more substituted R3, each is independent),
a pyrimidinyl group optionally substituted with 0 to 3 substituents with R3 (provided that, in the case of two or more substituted R3, each is independent),
a pyrazinyl group optionally substituted by R3 with 0 to 3 substituents (provided that, in the case of two or more substituted R3, each is independent),
a triazinyl group optionally substituted with 0 to 2 substituents with R3 (provided that, in the case of disubstituted R3, each is independent),
a tetrazinyl group optionally substituted with R3,
a thienyl group which may be optionally substituted with 0 to 3 substituents with R3 (provided, however, that each R3 is independently substituted with 2 or more substituents),
a thiazolyl group optionally substituted with 0 to 2 substituents at R3 (provided that, in the case of disubstituted R3, each is independent),
an isothiazolyl group optionally substituted with 0 to 2 substituents at R3 (provided, however, that in the case of disubstituted R3, each is independent),
or represents a thiadiazolyl group optionally substituted with R3,
R3 is
hydroxyl group,
cyano group,
nitro group,
halogen atom,
a C1 to C6 alkyl group optionally substituted with a substituent C,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with a substituent C,
a C2-C6 alkenyl group optionally substituted with a substituent C,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted with a substituent C,
a C2-C6 haloalkynyl group,
a C1-C6 alkoxy group optionally substituted with a substituent C,
a C1-C6 haloalkoxy group,
a C3-C8 cycloalkoxy group optionally substituted with a substituent C,
a C2-C6 alkenyloxy group optionally substituted with a substituent C,
a C2-C6 haloalkenyloxy group,
a C3-C6 alkynyloxy group optionally substituted with a substituent C,
a C3-C6 haloalkynyloxy group,
RdC (=O) - (wherein Rd is as defined above),
RdC(=O)O- (wherein Rd is as defined above),
a 3- to 6-membered ring group containing 1 to 2 oxygen atoms;
Rc-L- (wherein Rc and L are as defined above),
RaRbN- (wherein Ra and Rb are as defined above),
or ReC(=O)N(Rf)- (where Re and Rf are each independently a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 A haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or RaRbN— (wherein Ra and Rb are There is.) Represents.) Represents;
R4 is
hydrogen atom,
a C1 to C6 alkyl group optionally substituted with a substituent C,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with a substituent C,
a C2-C6 alkenyl group optionally substituted with a substituent C,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted with a substituent C,
a C2-C6 haloalkynyl group,
a phenyl group optionally substituted with 0 to 5 substituents D (provided that, in the case of disubstituted or more substituents D, each is independent),
a C1-C6 alkyl group having a phenyl group optionally substituted with 0 to 5 substituents D (provided that, in the case of disubstituted or more substituents D, each is independent);
a C1-C6 haloalkyl group having a phenyl group optionally substituted with 0 to 5 substituents D (provided that, in the case of disubstituted or more substituents D, each is independent);
or RaRbN- (wherein Ra and Rb are as defined above),
R5 is
hydrogen atom,
a C1 to C6 alkyl group optionally substituted with a substituent C,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with a substituent C,
a C2-C6 alkenyl group optionally substituted with a substituent C,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted with a substituent C,
a C2-C6 haloalkynyl group,
a phenyl group optionally substituted with 0 to 5 substituents D (provided that, in the case of disubstituted or more substituents D, each is independent),
a C1-C6 alkyl group having a phenyl group optionally substituted with 0 to 5 substituents D (provided that, in the case of disubstituted or more substituents D, each is independent);
a C1-C6 haloalkyl group having a phenyl group optionally substituted with 0 to 5 substituents D (provided that, in the case of disubstituted or more substituents D, each is independent);
or RdC (=O) - (wherein Rd is as defined above),
Alternatively, R4 and R5, together with the attached oxime structure (C=N-O),
an isoxazole ring optionally substituted with 0 to 2 substituents E (provided that, in the case of disubstituted substituents E, each is independent),
an isoxazoline ring optionally substituted with 0 to 4 substituents F (provided that, in the case of two or more substituents F, each is independent),
a benzisoxazole ring optionally substituted with 0 to 4 substituents D (provided that, in the case of two or more substituents D, each is independent);
Alternatively, a 5,6-dihydro-4H-1,2-oxazine ring optionally substituted with 0 to 6 substituents F (provided that, in the case of 2 or more substituents F, each is independent) is formed. represents what to do;
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- (wherein Rc and L are as defined above); at least one selected from the group consisting of;
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-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, a C2-C6 alkoxyalkoxy group, RaRbN. - (where Ra and Rb are as defined above), Rc-L- (wherein Rc and L are as defined above), RdC (=O) - (where Rd is as defined above), RdC(=O)O— (wherein Rd is as defined above) and a 3- to 6-membered ring group containing 1 to 2 oxygen atoms is at least one selected from the group;
Substituent D is a hydroxyl group, a cyano group, a nitro group, a halogen atom, a C1 to C6 alkyl group optionally substituted with a substituent B, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group, a C1 to at least one selected from the group consisting of a C6 alkoxy group, a C1-C6 haloalkoxy group and a C3-C8 cycloalkoxy group;
Substituent E is a hydroxyl group, a cyano group, a halogen atom, a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group, a C3-C8 optionally substituted with a substituent C A 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, a C2-C6 haloalkynyl group, C1-C6 alkoxy group optionally substituted with substituent C, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group optionally substituted with substituent C, substituent C C2-C6 alkenyloxy group optionally substituted with C2-C6 haloalkenyloxy group, C3-C6 alkynyloxy group optionally substituted with substituent C, C3-C6 haloalkynyloxy group , a C2-C6 alkoxyalkoxy group, RaRbN- (where Ra and Rb are as defined above), Rc-L- (wherein Rc and L are as defined above), RdC (=O)-(wherein Rd is as defined above), RdC(=O)O-(wherein Rd is as defined above), RgON=C(Rh)-( Here, Rg and Rh each independently represent a hydrogen atom or a C1-C6 alkyl group), RiRjRkSi- (wherein Ri, Rj and Rk each independently represent a C1-C6 represents an alkyl group) and at least one selected from the group consisting of a 3- to 6-membered ring group containing 1 to 2 oxygen atoms;
Substituent F is a hydroxyl group, a cyano group, a halogen atom, a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group, a C3-C8 optionally substituted with a substituent C A 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, a C2-C6 haloalkynyl group, C1-C6 alkoxy group optionally substituted with substituent C, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group optionally substituted with substituent C, substituent C C2-C6 alkenyloxy group optionally substituted with C2-C6 haloalkenyloxy group, C3-C6 alkynyloxy group optionally substituted with substituent C, C3-C6 haloalkynyloxy group , RaRbN- (wherein Ra and Rb are as defined above), Rc-L- (wherein Rc and L are as defined above), RdC (=O)- (where , Rd has the same meaning as defined above) and RdC(=O)O- (wherein Rd has the same meaning as defined above). ] or a salt thereof. R1 is
a C1-C6 alkyl group optionally substituted with a substituent A,
a C1-C6 haloalkyl group,
a C2-C6 alkenyl group optionally substituted with a substituent A,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted with a substituent A,
or represents a C2-C6 haloalkynyl group;
R2 is
hydrogen atom,
halogen atom,
a C1-C6 alkyl group optionally substituted with a substituent A,
a C1-C6 haloalkyl group,
a C2-C6 alkenyl group optionally substituted with a substituent A,
a C2-C6 alkynyl group optionally substituted with a substituent A,
a C1-C6 alkoxy group optionally substituted with a substituent A,
a C1-C6 haloalkoxy group,
Rc-L- (wherein Rc represents a C1-C6 alkyl group or a C1 _- C6 haloalkyl group, and L represents S, SO, or SO2),
or RdC(=O)-(wherein Rd is a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, C1 ~C6 alkoxy group, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group, or RaRbN- (wherein Ra and Rb are each independently and optionally substituted with a hydrogen atom, a substituent B may be a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group, or Ra and Rb together with the binding nitrogen atom are an aziridinyl group, an azetidinyl group , represents a pyrrolidinyl group, a piperidinyl group, a homopiperidinyl group, or an azocanyl group.) represents;
Y is
a phenyl group optionally substituted with 0 to 5 substituents with R3 (however, in the case of disubstituted or more R3, each is independent),
or R3 optionally represents a pyridyl group optionally substituted with 0 to 4 substituents (provided that, in the case of two or more substituted R3, each is independent),
R3 is
hydroxyl group,
cyano group,
halogen atom,
a C1 to C6 alkyl group optionally substituted with a substituent C,
a C1-C6 alkoxy group optionally substituted with a substituent C,
a C1-C6 haloalkoxy group,
a C2-C6 alkenyloxy group optionally substituted with a substituent C,
a C2-C6 haloalkenyloxy group,
a C3-C6 alkynyloxy group optionally substituted with a substituent C,
a C3-C6 haloalkynyloxy group,
or RdC (=O) O- (wherein Rd is as defined above);
R4 is
hydrogen atom,
a C1 to C6 alkyl group optionally substituted with a substituent C,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with a substituent C,
a C2-C6 alkenyl group optionally substituted with a substituent C,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted with a substituent C,
a C2-C6 haloalkynyl group,
a phenyl group optionally substituted with 0 to 5 substituents D (provided that, in the case of disubstituted or more substituents D, each is independent),
or RaRbN- (where Ra and Rb are as defined above),
R5 is
hydrogen atom,
a C1 to C6 alkyl group optionally substituted with a substituent C,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with a substituent C,
a C2-C6 alkenyl group optionally substituted with a substituent C,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted with a substituent C,
a C2-C6 haloalkynyl group,
or RdC (=O) - (wherein Rd is as defined above),
Alternatively, R4 and R5, together with the attached oxime structure (C=N-O),
an isoxazole ring optionally substituted with 0 to 2 substituents E (provided that, in the case of disubstituted substituents E, each is independent),
an isoxazoline ring optionally substituted with 0 to 4 substituents F (provided that, in the case of two or more substituents F, each is independent),
Alternatively, it forms a benzisoxazole ring optionally substituted with 0 to 4 substituents D (provided that, in the case of two or more substituents D, each is independent), according to claim 1 The described compound or a salt thereof. R1 is
a C1-C6 alkyl group optionally substituted with a substituent A,
or represents a C1-C6 haloalkyl group;
R2 is
halogen atom,
a C1-C6 alkyl group optionally substituted with a substituent A,
a C2-C6 alkynyl group optionally substituted with a substituent A,
or represents a C1-C6 alkoxy group optionally substituted with a substituent A;
Y is
a phenyl group optionally substituted with 0 to 5 substituents at R3 (provided, however, that each R3 is disubstituted or more is independent);
R3 is
cyano group,
halogen atom,
or represents a C1-C6 alkoxy group optionally substituted with a substituent C;
R4 is
hydrogen atom,
a C1 to C6 alkyl group optionally substituted with a substituent C,
a C3-C8 cycloalkyl group optionally substituted with a substituent C,
a phenyl group optionally substituted with 0 to 5 substituents D (provided that, in the case of disubstituted or more substituents D, each is independent),
or RaRbN- (wherein Ra and Rb are each independently a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, or a C3-C8 Alternatively, Ra and Rb together with the attached nitrogen atom form an aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl, homopiperidinyl, or azocanyl group). represent,
R5 is
hydrogen atom,
a C1 to C6 alkyl group optionally substituted with a substituent C,
or RdC(=O)-(wherein Rd is a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, C1 ~C6 alkoxy group, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group, or RaRbN- (wherein Ra and Rb are each independently and optionally substituted with a hydrogen atom, a substituent B may be a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group, or Ra and Rb together with the binding nitrogen atom are an aziridinyl group, an azetidinyl group , a pyrrolidinyl group, a piperidinyl group, a homopiperidinyl group, or an azocanyl group.
Alternatively, R4 and R5, together with the attached oxime structure (C=N-O),
an isoxazole ring optionally substituted with 0 to 2 substituents E (provided that, in the case of disubstituted substituents E, each is independent),
an isoxazoline ring optionally substituted with 0 to 4 substituents F (provided that, in the case of two or more substituents F, each is independent),
Alternatively, it forms a benzisoxazole ring optionally substituted with 0 to 4 substituents D (provided that, in the case of two or more substituents D, each is independent), according to claim 2 The described compound or a salt thereof. An agricultural and horticultural pesticide 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 for cultivating plants. A method for controlling plant diseases, which comprises applying the agricultural and horticultural fungicide according to claim 5 to plants, plant seeds, or soil for cultivating plants.