JPWO2018190349A1 - Pyridone compounds and fungicides for agricultural and horticultural use containing the same as active ingredients - Google Patents

Abstract

A novel compound for controlling a plant disease is provided. The pyridone compound of the present invention is a novel compound and can control plant diseases.

Description

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

  Various fungicides are used because controlling disease of agricultural and horticultural crops plays an important role in ensuring stable agricultural production. However, the use of fungicides for many years has led to the emergence of drug-resistant bacteria, and a new fungicide that is effective not only against drug-sensitive bacteria but also against drug-resistant bacteria is eagerly desired.

  With respect to 1,3,5,6-substituted-2-pyridone compounds, for example, 1,3,5,6-substituted-2-pyridones having an aryl group or a heteroaryl group at the 3-position as GABA alpha-2 / 3 ligand Compounds have been disclosed (see, for example, WO 98/55480). Further, 1,3,5,6-substituted-2-pyridone compounds having a carboxyl group at the 3-position have been disclosed as therapeutic agents for bacterial infectious diseases (see, for example, European Patent No. 0308020).

International Publication No. 98/55480 European Patent No. 0308020

However, WO 98/55480 and EP 0 308 020 disclose compounds whose 3-position substituents are completely different from those of the compounds according to the invention and which differ in their chemical structure. It's just that. In addition, the uses of the compounds described in the patent documents are all related to pharmaceuticals, which is different from the technical field to which the agricultural and horticultural fungicides according to the present invention belong.
An object of the present invention is to provide a novel compound that is effective as an agricultural and horticultural fungicide.

  The present inventors have conducted intensive studies on the 1,3,5,6-substituted-2-pyridone compound group and the 1,5,6-substituted-2-pyridone compound group in order to solve the above problems, With respect to the 6-position in the 2-pyridone skeleton, it has been found that a compound group in which an aryl group or heteroaryl group having a substituent at the ortho position is introduced exhibits excellent control activity against plant diseases, and the present invention It was completed.

  That is, the present invention is as follows.

［式中、Ｒ１は、
水酸基、
シアノ基、
置換基Ａで適宜置換されてもよいＣ１〜Ｃ６のアルキル基、
Ｃ１〜Ｃ６のハロアルキル基、
置換基Ａで適宜置換されてもよいＣ３〜Ｃ８のシクロアルキル基、
置換基Ａで適宜置換されてもよいＣ２〜Ｃ６のアルケニル基、
Ｃ２〜Ｃ６のハロアルケニル基、
置換基Ａで適宜置換されてもよいＣ２〜Ｃ６のアルキニル基、
Ｃ２〜Ｃ６のハロアルキニル基、
置換基Ａで適宜置換されてもよいＣ１〜Ｃ６のアルコキシ基、
Ｃ１〜Ｃ６のハロアルコキシ基、
置換基Ａで適宜置換されてもよいＣ３〜Ｃ８のシクロアルコキシ基、
置換基Ａで適宜置換されてもよいＣ２〜Ｃ６のアルケニルオキシ基、
Ｃ２〜Ｃ６のハロアルケニルオキシ基、
置換基Ａで適宜置換されてもよいＣ３〜Ｃ６のアルキニルオキシ基、
Ｃ３〜Ｃ６のハロアルキニルオキシ基、
またはＲ１０Ｒ１１Ｎ−（ここで、Ｒ１０およびＲ１１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。）を表し；
Ｒ２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、
置換基Ｂ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Ｂ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Ｂ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Ｂ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Ｂ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Ｂ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Ｂ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、
Ｒ２０Ｃ（＝Ｏ）−（ここで、Ｒ２０は、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Ｒ２１Ｒ２２Ｎ−（ここで、Ｒ２１およびＲ２２は、それぞれ独立していて、水素原子、置換基Ｂ１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Ｒ２１およびＲ２２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。）、
Ｒ２０Ｃ（＝Ｏ）Ｏ−（ここで、Ｒ２０は、前記と同義である。）、
Ｒ２１Ｒ２２Ｎ−（ここで、Ｒ２１およびＲ２２は、前記と同義である。）、
Ｒ２３−Ｌ２−（ここで、Ｒ２３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、Ｌ２は、Ｓ、ＳＯ、またはＳＯ_２を表す。）、
Ｒ２４Ｃ（＝Ｏ）Ｎ（Ｒ２５）−（ここで、Ｒ２４は、水素原子、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Ｒ２１Ｒ２２Ｎ−（ここで、Ｒ２１およびＲ２２は、前記と同義である。）を表し、Ｒ２５は、水素原子、置換基Ｂ１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。）、
または１〜２個の酸素原子を含む３〜６員環の基を表し；
Ｒ３は、
水素原子、
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、
Ｒ３０−Ｌ３−（ここで、Ｒ３０は、前記のＲ２３と同義であり、Ｌ３は、前記のＬ２と同義である。）、
Ｒ３１Ｒ３２Ｎ−（ここで、Ｒ３１およびＲ３２は、前記のＲ２１およびＲ２２と同義である。）、
またはＲ３３Ｃ（＝Ｏ）−（ここで、Ｒ３３は、Ｃ１〜Ｃ６のアルキル基、Ｃ１〜Ｃ６のハロアルキル基、またはＣ３〜Ｃ８のシクロアルキル基を表す。）を表し；
ｎは、０〜５の整数（ただし、ｎが２以上のとき、２以上のＲ２は、それぞれ独立した置換基を表す。）を表し；
Ｘは、酸素原子、または硫黄原子を表し；
Ｙは、
フェニル基、ピリジル基、ピリダジニル基、ピリミジニル基、ピラジニル基、トリアジニル基、チエニル基、チアゾリル基、または、イソチアゾリル基を表し、
該フェニル基は、置換基Ｄがオルト位に置換し、置換基Ｄ１が、それぞれ独立して適宜０〜３置換し、さらに置換基Ｄ２が、それぞれ独立して適宜１〜４置換し、
該ピリジル基、該ピリダジニル基、該ピリミジニル基、該ピラジニル基、または該トリアジニル基は、置換基Ｄがオルト位に置換し、置換基Ｄ１が、それぞれ独立して適宜０〜２置換し、さらに置換基Ｄ２が、それぞれ独立して適宜１〜３置換し、
該チエニル基、該チアゾリル基、または該イソチアゾリル基は、置換基Ｄがオルト位に置換し、置換基Ｄ１が、それぞれ独立して適宜０〜１置換し、さらに置換基Ｄ２が、それぞれ独立して適宜１〜２置換し；
破線部を含む結合は、二重結合、または単結合を表し；
そして、置換基Ａは、
水酸基、シアノ基、Ｃ３〜Ｃ８のシクロアルキル基、Ｃ１〜Ｃ６のアルコキシ基、Ｃ１〜Ｃ６のハロアルコキシ基、Ｃ３〜Ｃ８のシクロアルコキシ基、Ｒ１２Ｒ１３Ｎ−（ここで、Ｒ１２およびＲ１３は、それぞれ独立していて、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か、あるいはＲ１２およびＲ１３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。）、およびＲ１４−Ｌ１−（ここで、Ｒ１４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、Ｌ１は、Ｓ、ＳＯ、またはＳＯ_２を表す。）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、
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、Ｒ２１Ｒ２２Ｎ−（ここで、Ｒ２１およびＲ２２は、前記と同義である。）、Ｒ２３−Ｌ２−（ここで、Ｒ２３およびＬ２は、前記と同義である。）、Ｒ２６Ｒ２７Ｒ２８Ｓｉ−（ここで、Ｒ２６、Ｒ２７およびＲ２８は、それぞれ独立していてＣ１〜Ｃ６のアルキル基を表す。）、Ｒ２６Ｒ２７Ｒ２８Ｓｉ−（ＣＨ_２）ｓ−Ｏ−（ここで、ｓは、１〜３の整数を表し、Ｒ２６、Ｒ２７およびＲ２８は、前記と同義である。）、Ｒ２０Ｃ（＝Ｏ）−（ここで、Ｒ２０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Ｂ１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、Ｒ３１Ｒ３２Ｎ−（ここで、Ｒ３１およびＲ３２は、前記のＲ２１およびＲ２２と同義である。）、およびＲ３０−Ｌ３−（ここで、Ｒ３０は、前記のＲ２３と同義であり、Ｌ３は、前記のＬ２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Ｄ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、およびＣ１〜Ｃ６のハ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Ｄ１は、
水酸基、ハロゲン原子、Ｃ１〜Ｃ６のアルキル基、Ｃ１〜Ｃ６のハロアルキル基、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Ｄ２は、
シアノ基、
ニトロ基、
置換基Ｂで適宜置換されてもよいＣ２〜Ｃ６のアルケニル基、
Ｃ２〜Ｃ６ハロアルケニル基、
置換基Ｂ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Ｂ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Ｂ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、
Ｃ２〜Ｃ６のシアノアルコキシ基、
Ｃ４〜Ｃ９のシクロアルキルアルコキシ基、
置換基Ｄで適宜置換されてもよいアリール基、
置換基Ｄで適宜置換されてもよいヘテロアリール基、
置換基Ｄで適宜置換されてもよいアリールオキシ基、
置換基Ｄで適宜置換されてもよいヘテロアリールオキシ基、
置換基Ｄで適宜置換されてもよいアラルキルオキシ基、
Ｒ４０（ＣＨ２）ｐ−Ｕ−（ここで、ｐは、１〜３の整数を表し、Ｒ４０は１〜２個の酸素原子を含む３〜６員環の基、Ｒ４１Ｒ４２Ｎ−（ここで、Ｒ４１およびＲ４２は、前記のＲ２１およびＲ２２と同義である。）、またはＲ４３−Ｌ４−（ここで、Ｒ４３は、前記のＲ１４と同義であり、Ｌ４は、前記のＬ１と同義である。）を表し、Ｕは、酸素原子、または硫黄原子を表す。）、
Ｒ４１Ｒ４２Ｎ−（ここで、Ｒ４１およびＲ４２は前記と同義である。）、
Ｒ４３−Ｌ４−（ここで、Ｒ４３は、前記のＲ１４と同義であり、Ｌ４は、前記のＬ１と同義である。）、
Ｒ４４Ｃ（＝Ｏ）−（ここで、Ｒ４４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Ｒ４１Ｒ４２Ｎ−（ここで、Ｒ４１およびＲ４２は前記と同義である。）を表す。）、
Ｒ４４Ｃ（＝Ｏ）Ｏ−（ここで、Ｒ４４は、前記と同義である。）、
Ｒ４５Ｃ（＝Ｏ）Ｎ（Ｒ４６）−（ここで、Ｒ４５は、水素原子、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、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Ｒ４１Ｒ４２Ｎ−（ここで、Ｒ４１およびＲ４２は、前記と同義である。）を表し、Ｒ４６は、水素原子、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、またはＣ３〜Ｃ８のシクロアルキル基を表す。）、
Ｒ４７Ｒ４８Ｃ＝Ｎ−Ｏ−（ここで、Ｒ４７およびＲ４８は、それぞれ独立していて、水素原子、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、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Ｒ４１Ｒ４２Ｎ−（ここで、Ｒ４１およびＲ４２は、前記と同義である。）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種である］で表される化合物またはその塩。[1] Equation (1)

Wherein R1 is
Hydroxyl group,
Cyano group,
A C1-C6 alkyl group optionally substituted with a substituent A,
A C1-C6 haloalkyl group,
A C3-C8 cycloalkyl group optionally substituted with a substituent A,
A C2-C6 alkenyl group optionally substituted with a substituent A,
A C2-C6 haloalkenyl group,
A C2-C6 alkynyl group optionally substituted with a substituent A,
A C2-C6 haloalkynyl group,
A C1-C6 alkoxy group optionally substituted with a substituent A,
A C1-C6 haloalkoxy group,
A C3-C8 cycloalkoxy group optionally substituted with a substituent A,
A C2-C6 alkenyloxy group optionally substituted with a substituent A,
A C2-C6 haloalkenyloxy group,
A C3-C6 alkynyloxy group optionally substituted with a substituent A,
A C3-C6 haloalkynyloxy group,
Or R10R11N- (wherein R10 and R11 are each independently a hydrogen atom or a C1-C6 alkyl group);
R2 is
Hydroxyl group,
Cyano group,
Nitro group,
Halogen atom,
A C1-C6 alkyl group optionally substituted with a substituent B,
A C1-C6 haloalkyl group,
A C3-C8 cycloalkyl group optionally substituted with a substituent B,
A C2-C6 alkenyl group optionally substituted with substituent B,
A C2-C6 haloalkenyl group,
A C2-C6 alkynyl group optionally substituted with a substituent B,
A C2-C6 haloalkynyl group,
A C1-C6 alkoxy group optionally substituted with a substituent B,
A C1-C6 haloalkoxy group,
A C3-C8 cycloalkoxy group optionally substituted with a substituent B,
A C2-C6 alkenyloxy group optionally substituted with a substituent B,
A C2-C6 haloalkenyloxy group,
A C3-C6 alkynyloxy group optionally substituted with a substituent B,
A C3-C6 haloalkynyloxy group,
R20C (= O)-(where R20 is a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, A C3-C8 cycloalkoxy group, or R21R22N- (wherein R21 and R22 are each independently a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B1, a C1-C6 Represents a haloalkyl group, or a C3-C8 cycloalkyl group, or R21 and R22, together with the nitrogen atom to which they are attached, represent an aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl, homopiperidinyl, or azocanyl group; Represents what is formed.).),
R20C (= O) O- (where R20 has the same meaning as described above),
R21R22N- (where R21 and R22 are as defined above),
R23-L2- (wherein, R23 represents an alkyl group or a haloalkyl group of C1 -C6, a C1 -C6, L2 represents S, SO, or SO _2.),
R24C (= O) N (R25)-(where R24 is a hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1 Represents a haloalkoxy group of C6 to C6, a cycloalkoxy group of C3 to C8, or R21R22N- (where R21 and R22 have the same meanings as described above), and R25 is appropriately substituted with a hydrogen atom or a substituent B1. Represents a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, or a C3 to C8 cycloalkyl group.)
Or a 3- to 6-membered ring group containing 1 to 2 oxygen atoms;
R3 is
Hydrogen atom,
Nitro group,
Halogen 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 C1-C6 alkoxy group optionally substituted with a substituent C,
A C1-C6 haloalkoxy group,
R30-L3- (where R30 has the same meaning as R23, and L3 has the same meaning as L2);
R31R32N- (where R31 and R32 have the same meanings as R21 and R22 described above),
Or R33C (= O)-(where R33 represents a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group);
n represents an integer of 0 to 5 (however, when n is 2 or more, 2 or more R2 represents an independent substituent);
X represents an oxygen atom or a sulfur atom;
Y is
A phenyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, a thienyl group, a thiazolyl group, or an isothiazolyl group;
In the phenyl group, the substituent D is substituted at the ortho position, the substituent D1 is independently substituted with 0 to 3 as appropriate, and further the substituent D2 is independently substituted with 1 to 4 as appropriate.
In the pyridyl group, the pyridazinyl group, the pyrimidinyl group, the pyrazinyl group, or the triazinyl group, the substituent D is substituted at the ortho position, and the substituents D1 are each independently optionally substituted with 0 to 2, and further substituted. Groups D2 are each independently appropriately substituted with 1 to 3,
In the thienyl group, the thiazolyl group, or the isothiazolyl group, the substituent D is substituted at the ortho position, the substituents D1 are each independently optionally substituted with 0 to 1, and the substituents D2 are each independently substituted. Substitute 1-2 as appropriate;
A bond containing a broken line represents a double bond or a single bond;
And the substituent A is
Hydroxyl group, cyano group, C3-C8 cycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group, R12R13N- (where R12 and R13 are each independently And represents a hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group, or R12 and R13 together with the bonding nitrogen atom form an aziridinyl group , Azetidinyl group, pyrrolidinyl group, piperidinyl group, homopiperidinyl group, or azocanyl group), and R14-L1- (where R14 is a C1-C6 alkyl group, or a C1-C6 haloalkyl). represents a group, is selected L1 is, S, SO, or from the group consisting of.) representing the SO _2, At least one of the following:
Substituent B 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, R21R22N- R21 and R22 are as defined above, R23-L2- (where R23 and L2 are as defined above), R26R27R28Si- (where R26, R27 and R28 are each independently represents an alkyl group having C1~C6 _{have.), R26R27R28Si- (CH 2)} s-O- ( wherein, s represents an integer of 1 to 3, R26, R27 and R28 is a as defined above ), R20C (= O)-(where R20 has the same meaning as described above), and a 3- to 6-membered ring group containing 1 to 2 oxygen atoms. That is at least one selected from the group;
The substituent B1 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, R31R32N- (where R31 and R32 are the aforementioned R21 And R22 and R30-L3- (where R30 has the same meaning as R23, and L3 has the same meaning as L2). Species;
Substituent D is
At least one selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, and a C1-C6 haloalkoxy group;
The substituent D1 is
Hydroxyl group, halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, and C3-C8 cycloalkoxy group At least one selected from the group consisting of:
The substituent D2 is
Cyano group,
Nitro group,
A C2-C6 alkenyl group optionally substituted with substituent B,
A C2-C6 haloalkenyl group,
A C2-C6 alkynyl group optionally substituted with a substituent B,
A C2-C6 haloalkynyl group,
A C2-C6 alkenyloxy group optionally substituted with a substituent B,
A C2-C6 haloalkenyloxy group,
A C3-C6 alkynyloxy group optionally substituted with a substituent B,
A C3-C6 haloalkynyloxy group,
A C2-C6 alkoxyalkoxy group,
A C2-C6 cyanoalkoxy group,
A C4-C9 cycloalkylalkoxy group,
An aryl group optionally substituted with a substituent D,
A heteroaryl group optionally substituted with a substituent D,
An aryloxy group optionally substituted with a substituent D,
A heteroaryloxy group optionally substituted with a substituent D,
An aralkyloxy group optionally substituted with a substituent D,
R40 (CH2) pU- (where p represents an integer of 1 to 3, and R40 is a 3- to 6-membered ring group containing 1 to 2 oxygen atoms, R41R42N- (where R41 and R42 has the same meaning as R21 and R22 described above; or R43-L4- (where R43 has the same meaning as R14, and L4 has the same meaning as L1); U represents an oxygen atom or a sulfur atom.),
R41R42N- (where R41 and R42 are as defined above),
R43-L4- (where R43 has the same meaning as R14, and L4 has the same meaning as L1);
R44C (＝ O)-(where R44 is a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group which may be appropriately substituted with a substituent B A group, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group, or R41R42N- (where R41 and R42 have the same meanings as described above),
R44C (= O) O- (where R44 is as defined above),
R45C (＝ O) N (R46)-(where R45 is a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl A group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or R41R42N- (where R41 and R42 have the same meanings as described above); A hydrogen atom, a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, or a C3 to C8 cycloalkyl group which may be appropriately substituted with a substituent A);
R47R48C = N-O- (where R47 and R48 are each independently a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C Represents a C8 cycloalkyl group, a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group, or R41R42N- (where R41 and R42 have the same meanings as described above). .),
And at least one member selected from the group consisting of a 3- to 6-membered ring group containing 1 or 2 oxygen atoms.] Or a salt thereof.

[2] R1 is
Cyano group,
A C1-C6 alkyl group optionally substituted with a substituent A,
A C1-C6 haloalkyl group,
A C3-C8 cycloalkyl group optionally substituted with a substituent A,
A C2-C6 alkenyl group optionally substituted with a substituent A,
A C2-C6 haloalkenyl group,
A C2-C6 alkynyl group optionally substituted with a substituent A,
Or R10R11N- (wherein R10 and R11 are each independently a hydrogen atom or a C1-C6 alkyl group);
R2 is
Hydroxyl group,
Cyano group,
Halogen atom,
A C1-C6 alkyl group optionally substituted with a substituent B,
A C1-C6 haloalkyl group,
A C1-C6 alkoxy group optionally substituted with a substituent B,
A C1-C6 haloalkoxy group,
A C3-C8 cycloalkoxy group optionally substituted with a substituent B,
A C2-C6 alkenyloxy group optionally substituted with a substituent B,
A C3-C6 alkynyloxy group optionally substituted with a substituent B,
R20C (= O) O- (where R20 is a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group , A C3-C8 cycloalkoxy group, or R21R22N- (wherein R21 and R22 are each independently a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B1, a C1-C6 Represents a haloalkyl group or a C3-C8 cycloalkyl group, or R21 and R22 together with a bonding nitrogen atom form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, a piperidinyl group, a homopiperidinyl group, or an azocanyl group Represents what forms).
Or R23-L2- (wherein, R23 represents an alkyl group or a haloalkyl group of C1 -C6, a C1 -C6, L2 is S, SO, or an SO _2.) Represents;
R3 is
Hydrogen atom,
Halogen atom,
A C1-C6 alkyl group optionally substituted with a substituent C,
A C3-C8 cycloalkyl group optionally substituted with a substituent C,
A C2-C6 alkynyl group optionally substituted with a substituent C,
A C1-C6 alkoxy group optionally substituted with a substituent C,
Or R30-L3- (where R30 has the same meaning as R23, and L3 has the same meaning as L2);
Y represents a phenyl group or a pyridyl group,
In the phenyl group, the substituent D is substituted at the ortho position, the substituent D1 is independently substituted with 0 to 3 as appropriate, and further the substituent D2 is independently substituted with 1 to 4 as appropriate.
In the pyridyl group, the substituent D is substituted at the ortho-position, the substituent D1 is independently optionally substituted with 0 to 2, and the substituent D2 is each independently substituted with 1 to 3 as appropriate;
The substituent D2 is
Cyano group,
A C2-C6 alkenyl group optionally substituted with substituent B,
A C2-C6 alkynyl group optionally substituted with a substituent B,
A C2-C6 alkenyloxy group optionally substituted with a substituent B,
A C3-C6 alkynyloxy group optionally substituted with a substituent B,
A C2-C6 alkoxyalkoxy group,
A C2-C6 cyanoalkoxy group,
A C4-C9 cycloalkylalkoxy group,
A heteroaryl group optionally substituted with a substituent D,
An aryloxy group optionally substituted with a substituent D,
An aralkyloxy group optionally substituted with a substituent D,
R40 (CH2) pU- (where p represents an integer of 1 to 3, and R40 is a 3- to 6-membered ring group containing 1 to 2 oxygen atoms, R41R42N- (where R41 and R42 is each independently a hydrogen atom, a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, or a C3 to C8 cycloalkyl group which may be appropriately substituted with a substituent B1; And R42 represents a group which forms an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, a piperidinyl group, a homopiperidinyl group, or an azocanyl group together with the nitrogen atom to be bonded thereto, or R43-L4- (wherein R43 represents a C1 to C6 alkyl group or a C1 to C6 haloalkyl group; L4 represents S, SO, or SO2), and U represents an acid. Atom or a sulfur atom.),
R41R42N- (where R41 and R42 are as defined above),
R43-L4- (where R43 and L4 are as defined above),
R44C (＝ O) O— (where R44 is a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group, a C1 to C6 An alkoxy group, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group, or R41R42N- (where R41 and R42 have the same meanings as described above);
And R47R48C = NO- (where R47 and R48 are each independently a hydrogen atom, a C1 to C6 alkyl group optionally substituted with a substituent A, a C1 to C6 haloalkyl group, A C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or R41R42N- (where R41 and R42 are as defined above). The compound according to [1], or a salt thereof, which is at least one member selected from the group consisting of:

[3] R1 is
A C1-C6 alkyl group optionally substituted with a substituent A,
Or a C1-C6 haloalkyl group;
R2 is
Halogen atom,
A C1-C6 alkyl group optionally substituted with a substituent B,
A C1-C6 alkoxy group optionally substituted with a substituent B,
Or R23-L2- (wherein, R23 represents an alkyl group or a haloalkyl group of C1 -C6, a C1 -C6, L2 is S, SO, or an SO _2.) Represents;
R3 is
Hydrogen atom,
Halogen atom,
Or a C1-C6 alkyl group optionally substituted with a substituent C;
Y represents a phenyl group,
In the phenyl group, the substituent D is substituted at the ortho-position, the substituent D1 is independently substituted with 0 to 3 as appropriate, and the substituent D2 is independently substituted with 1 to 4 as appropriate. Or a salt thereof.

［式中、Ｒ２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、
置換基Ｂ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Ｂ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Ｂ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Ｂ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Ｂ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Ｂ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Ｂ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、
Ｒ２０Ｃ（＝Ｏ）−（ここで、Ｒ２０は、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Ｒ２１Ｒ２２Ｎ−（ここで、Ｒ２１およびＲ２２は、それぞれ独立していて、水素原子、置換基Ｂ１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Ｒ２１およびＲ２２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。）、
Ｒ２０Ｃ（＝Ｏ）Ｏ−（ここで、Ｒ２０は、前記と同義である。）、
Ｒ２１Ｒ２２Ｎ−（ここで、Ｒ２１およびＲ２２は、前記と同義である。）、
Ｒ２３−Ｌ２−（ここで、Ｒ２３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、Ｌ２は、Ｓ、ＳＯ、またはＳＯ_２を表す。）、
Ｒ２４Ｃ（＝Ｏ）Ｎ（Ｒ２５）−（ここで、Ｒ２４は、水素原子、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Ｒ２１Ｒ２２Ｎ−（ここで、Ｒ２１およびＲ２２は、前記と同義である。）を表し、Ｒ２５は、水素原子、置換基Ｂ１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。）、
または１〜２個の酸素原子を含む３〜６員環の基を表し；
Ｒ３は、
水素原子、
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、
Ｒ３０−Ｌ３−（ここで、Ｒ３０は、前記のＲ２３と同義であり、Ｌ３は、前記のＬ２と同義である。）、
Ｒ３１Ｒ３２Ｎ−（ここで、Ｒ３１およびＲ３２は、前記のＲ２１およびＲ２２と同義である。）、
またはＲ３３Ｃ（＝Ｏ）−（ここで、Ｒ３３は、Ｃ１〜Ｃ６のアルキル基、Ｃ１〜Ｃ６のハロアルキル基、またはＣ３〜Ｃ８のシクロアルキル基を表す。）を表し；
ｎは、０〜５の整数（ただし、ｎが２以上のとき、２以上のＲ２は、それぞれ独立した置換基を表す。）を表し；
Ｘは、酸素原子、または硫黄原子を表し；
Ｙは、フェニル基、ピリジル基、ピリダジニル基、ピリミジニル基、ピラジニル基、トリアジニル基、チエニル基、チアゾリル基、または、イソチアゾリル基を表し、
該フェニル基は、置換基Ｄがオルト位に置換し、置換基Ｄ１が、それぞれ独立して適宜０〜３置換し、さらに置換基Ｄ２が、それぞれ独立して適宜１〜４置換し、
該ピリジル基、該ピリダジニル基、該ピリミジニル基、該ピラジニル基、または該トリアジニル基は、置換基Ｄがオルト位に置換し、置換基Ｄ１が、それぞれ独立して適宜０〜２置換し、さらに置換基Ｄ２が、それぞれ独立して適宜１〜３置換し、
該チエニル基、該チアゾリル基、または該イソチアゾリル基は、置換基Ｄがオルト位に置換し、置換基Ｄ１が、それぞれ独立して適宜０〜１置換し、さらに置換基Ｄ２が、それぞれ独立して適宜１〜２置換し；
そして、置換基Ｂ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、Ｒ２１Ｒ２２Ｎ−（ここで、Ｒ２１およびＲ２２は、前記と同義である。）、Ｒ２３−Ｌ２−（ここで、Ｒ２３およびＬ２は、前記と同義である。）、Ｒ２６Ｒ２７Ｒ２８Ｓｉ−（ここで、Ｒ２６、Ｒ２７およびＲ２８は、それぞれ独立していてＣ１〜Ｃ６のアルキル基を表す。）、Ｒ２６Ｒ２７Ｒ２８Ｓｉ−（ＣＨ_２）ｓ−Ｏ−（ここで、ｓは、１〜３の整数を表し、Ｒ２６、Ｒ２７およびＲ２８は、前記と同義である。）、Ｒ２０Ｃ（＝Ｏ）−（ここで、Ｒ２０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Ｂ１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、Ｒ３１Ｒ３２Ｎ−（ここで、Ｒ３１およびＲ３２は、前記のＲ２１およびＲ２２と同義である。）、およびＲ３０−Ｌ３−（ここで、Ｒ３０は、前記のＲ２３と同義であり、Ｌ３は、前記のＬ２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Ｄ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、およびＣ１〜Ｃ６のハ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Ｄ１は、
水酸基、ハロゲン原子、Ｃ１〜Ｃ６のアルキル基、Ｃ１〜Ｃ６のハロアルキル基、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Ｄ２は、
シアノ基、
ニトロ基、
置換基Ｂで適宜置換されてもよいＣ２〜Ｃ６のアルケニル基、
Ｃ２〜Ｃ６ハロアルケニル基、
置換基Ｂ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Ｂ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Ｂ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、
Ｃ２〜Ｃ６のシアノアルコキシ基、
Ｃ４〜Ｃ９のシクロアルキルアルコキシ基、
置換基Ｄで適宜置換されてもよいアリール基、
置換基Ｄで適宜置換されてもよいヘテロアリール基、
置換基Ｄで適宜置換されてもよいアリールオキシ基、
置換基Ｄで適宜置換されてもよいヘテロアリールオキシ基、
置換基Ｄで適宜置換されてもよいアラルキルオキシ基、
Ｒ４０（ＣＨ２）ｐ−Ｕ−（ここで、ｐは、１〜３の整数を表し、Ｒ４０は１〜２個の酸素原子を含む３〜６員環の基、Ｒ４１Ｒ４２Ｎ−（ここで、Ｒ４１およびＲ４２は、前記のＲ２１およびＲ２２と同義である。）、またはＲ４３−Ｌ４−（ここで、Ｒ４３は、前記のＲ１４と同義であり、Ｌ４は、前記のＬ１と同義である。）を表し、Ｕは、酸素原子、または硫黄原子を表す。）、
Ｒ４１Ｒ４２Ｎ−（ここで、Ｒ４１およびＲ４２は前記と同義である。）、
Ｒ４３−Ｌ４−（ここで、Ｒ４３は、前記のＲ１４と同義であり、Ｌ４は、前記のＬ１と同義である。）、
Ｒ４４Ｃ（＝Ｏ）−（ここで、Ｒ４４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Ｒ４１Ｒ４２Ｎ−（ここで、Ｒ４１およびＲ４２は前記と同義である。）を表す。）、
Ｒ４４Ｃ（＝Ｏ）Ｏ−（ここで、Ｒ４４は、前記と同義である。）、
Ｒ４５Ｃ（＝Ｏ）Ｎ（Ｒ４６）−（ここで、Ｒ４５は、水素原子、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、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Ｒ４１Ｒ４２Ｎ−（ここで、Ｒ４１およびＲ４２は、前記と同義である。）を表し、Ｒ４６は、水素原子、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、またはＣ３〜Ｃ８のシクロアルキル基を表す。）、
Ｒ４７Ｒ４８Ｃ＝Ｎ−Ｏ−（ここで、Ｒ４７およびＲ４８は、それぞれ独立していて、水素原子、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、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Ｒ４１Ｒ４２Ｎ−（ここで、Ｒ４１およびＲ４２は、前記と同義である。）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種である。］で表される化合物またはその塩。[4] Equation (2)

Wherein R2 is
Hydroxyl group,
Cyano group,
Nitro group,
Halogen atom,
A C1-C6 alkyl group optionally substituted with a substituent B,
A C1-C6 haloalkyl group,
A C3-C8 cycloalkyl group optionally substituted with a substituent B,
A C2-C6 alkenyl group optionally substituted with substituent B,
A C2-C6 haloalkenyl group,
A C2-C6 alkynyl group optionally substituted with a substituent B,
A C2-C6 haloalkynyl group,
A C1-C6 alkoxy group optionally substituted with a substituent B,
A C1-C6 haloalkoxy group,
A C3-C8 cycloalkoxy group optionally substituted with a substituent B,
A C2-C6 alkenyloxy group optionally substituted with a substituent B,
A C2-C6 haloalkenyloxy group,
A C3-C6 alkynyloxy group optionally substituted with a substituent B,
A C3-C6 haloalkynyloxy group,
R20C (= O)-(where R20 is a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, A C3-C8 cycloalkoxy group, or R21R22N- (wherein R21 and R22 are each independently a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B1, a C1-C6 Represents a haloalkyl group, or a C3-C8 cycloalkyl group, or R21 and R22, together with the nitrogen atom to which they are attached, represent an aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl, homopiperidinyl, or azocanyl group; Represents what is formed.).),
R20C (= O) O- (where R20 has the same meaning as described above),
R21R22N- (where R21 and R22 are as defined above),
R23-L2- (wherein, R23 represents an alkyl group or a haloalkyl group of C1 -C6, a C1 -C6, L2 represents S, SO, or SO _2.),
R24C (= O) N (R25)-(where R24 is a hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1 Represents a haloalkoxy group of C6 to C6, a cycloalkoxy group of C3 to C8, or R21R22N- (where R21 and R22 have the same meanings as described above), and R25 is appropriately substituted with a hydrogen atom or a substituent B1. Represents a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, or a C3 to C8 cycloalkyl group.)
Or a 3- to 6-membered ring group containing 1 to 2 oxygen atoms;
R3 is
Hydrogen atom,
Nitro group,
Halogen 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 C1-C6 alkoxy group optionally substituted with a substituent C,
A C1-C6 haloalkoxy group,
R30-L3- (where R30 has the same meaning as R23, and L3 has the same meaning as L2);
R31R32N- (where R31 and R32 have the same meanings as R21 and R22 described above),
Or R33C (= O)-(where R33 represents a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group);
n represents an integer of 0 to 5 (however, when n is 2 or more, 2 or more R2 represents an independent substituent);
X represents an oxygen atom or a sulfur atom;
Y represents a phenyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, a thienyl group, a thiazolyl group, or an isothiazolyl group;
In the phenyl group, the substituent D is substituted at the ortho position, the substituent D1 is independently substituted with 0 to 3 as appropriate, and further the substituent D2 is independently substituted with 1 to 4 as appropriate.
In the pyridyl group, the pyridazinyl group, the pyrimidinyl group, the pyrazinyl group, or the triazinyl group, the substituent D is substituted at the ortho position, and the substituents D1 are each independently optionally substituted with 0 to 2, and further substituted. Groups D2 are each independently appropriately substituted with 1 to 3,
In the thienyl group, the thiazolyl group, or the isothiazolyl group, the substituent D is substituted at the ortho position, the substituents D1 are each independently optionally substituted with 0 to 1, and the substituents D2 are each independently substituted. Substitute 1-2 as appropriate;
And the substituent B 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, R21R22N- R21 and R22 are as defined above, R23-L2- (where R23 and L2 are as defined above), R26R27R28Si- (where R26, R27 and R28 are each independently represents an alkyl group having C1~C6 _{have.), R26R27R28Si- (CH 2)} s-O- ( wherein, s represents an integer of 1 to 3, R26, R27 and R28 is a as defined above ), R20C (= O)-(where R20 has the same meaning as described above), and a 3- to 6-membered ring group containing 1 to 2 oxygen atoms. That is at least one selected from the group;
The substituent B1 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, R31R32N- (where R31 and R32 are the aforementioned R21 And R22 and R30-L3- (where R30 has the same meaning as R23, and L3 has the same meaning as L2). Species;
Substituent D is
At least one selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, and a C1-C6 haloalkoxy group;
The substituent D1 is
Hydroxyl group, halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, and C3-C8 cycloalkoxy group At least one selected from the group consisting of:
The substituent D2 is
Cyano group,
Nitro group,
A C2-C6 alkenyl group optionally substituted with substituent B,
A C2-C6 haloalkenyl group,
A C2-C6 alkynyl group optionally substituted with a substituent B,
A C2-C6 haloalkynyl group,
A C2-C6 alkenyloxy group optionally substituted with a substituent B,
A C2-C6 haloalkenyloxy group,
A C3-C6 alkynyloxy group optionally substituted with a substituent B,
A C3-C6 haloalkynyloxy group,
A C2-C6 alkoxyalkoxy group,
A C2-C6 cyanoalkoxy group,
A C4-C9 cycloalkylalkoxy group,
An aryl group optionally substituted with a substituent D,
A heteroaryl group optionally substituted with a substituent D,
An aryloxy group optionally substituted with a substituent D,
A heteroaryloxy group optionally substituted with a substituent D,
An aralkyloxy group optionally substituted with a substituent D,
R40 (CH2) pU- (where p represents an integer of 1 to 3, and R40 is a 3- to 6-membered ring group containing 1 to 2 oxygen atoms, R41R42N- (where R41 and R42 has the same meaning as R21 and R22 described above; or R43-L4- (where R43 has the same meaning as R14, and L4 has the same meaning as L1); U represents an oxygen atom or a sulfur atom.),
R41R42N- (where R41 and R42 are as defined above),
R43-L4- (where R43 has the same meaning as R14, and L4 has the same meaning as L1);
R44C (＝ O)-(where R44 is a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group which may be appropriately substituted with a substituent B A group, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group, or R41R42N- (where R41 and R42 have the same meanings as described above),
R44C (= O) O- (where R44 is as defined above),
R45C (＝ O) N (R46)-(where R45 is a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl A group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or R41R42N- (where R41 and R42 have the same meanings as described above); A hydrogen atom, a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, or a C3 to C8 cycloalkyl group which may be appropriately substituted with a substituent A);
R47R48C = N-O- (where R47 and R48 are each independently a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C Represents a C8 cycloalkyl group, a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group, or R41R42N- (where R41 and R42 have the same meanings as described above). .),
And at least one selected from the group consisting of a 3- to 6-membered ring group containing 1 to 2 oxygen atoms. Or a salt thereof.

[5] R1 is
The compound according to any one of [1] to [3], which represents a C1 to C6 alkyl group, or a salt thereof.

[6] R1 is
The compound according to any one of [1] to [3], which represents a methyl group, an ethyl group, a propyl group, a 2,2-difluoroethyl group, or a 2,2,2-trifluoroethyl group, or a compound thereof. salt.

[7] R1 is
The compound according to any one of [1] to [3], which represents a methyl group or an ethyl group, or a salt thereof.

[8] R2 is
Halogen atom, an alkoxy group C1 -C6 or R23-L2- (where,, R23 represents an alkyl group or a haloalkyl group of C1 -C6, a C1 -C6, L2 is S, SO, or SO ₂ The compound according to any one of [1] to [3] and [5] to [7], or a salt thereof.

[9] R2 is
Fluorine, chlorine, bromine, iodine, methyl, ethyl, methoxy, ethoxy, propyloxy, isopropyloxy, methylthio, methanesulfinyl, methanesulfonyl, (chloromethyl) thio, The compound according to any one of [1] to [3] and [5] to [7], which represents a (chloromethane) sulfinyl group or a (chloromethane) sulfonyl group, or a salt thereof.

[10] R2 is
The compound according to any one of [1] to [3], [5] to [7], which represents a fluorine atom, a chlorine atom, a methoxy group, or a methylthio group, or a salt thereof.

[11] R3 is
The compound according to any one of [1] to [3], [5] to [10], which represents a hydrogen atom, a halogen atom, or a C1 to C6 alkyl group, or a salt thereof.

[12] R3 is
Any one of [1] to [3], [5] to [10], representing a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a methyl group, an ethyl group, or a propyl group; A compound or a salt thereof.

[13] R3 is
The compound according to any one of [1] to [3], [5] to [10], which represents a hydrogen atom, a chlorine atom, a bromine atom, or a methyl group, or a salt thereof.

[14] The substituent D is
The compound according to any one of [1] to [3], [5] to [13], which represents a fluorine atom, a chlorine atom, or a bromine atom, or a salt thereof.

[15] The substituent D is
The compound according to any one of [1] to [3] and [5] to [13], which represents a fluorine atom, or a salt thereof.

[16] The substituent D1 is
The compound according to any one of [1] to [3], [5] to [15], which represents a halogen atom, a C1 to C6 alkyl group, or a C1 to C6 alkoxy group, or a salt thereof.

[17] The substituent D1 is
The compound according to any one of [1] to [3] and [5] to [15], which represents a halogen atom, or a salt thereof.

[18] The substituent D1 is
The compound according to any one of [1] to [3] and [5] to [15], which represents a fluorine atom, or a salt thereof.

[19] The substituent D2 is
A cyano group, a C2 to C6 alkynyl group optionally substituted with a substituent B, a C2 to C6 alkenyloxy group optionally substituted with a substituent B, and a C3 to C3 optionally substituted with a substituent B C6 alkynyloxy group, C2 to C6 alkoxyalkoxy group, C2 to C6 cyanoalkoxy group, C4 to C9 cycloalkylalkoxy group, heteroaryl group optionally substituted by substituent D, An optionally substituted aryloxy group, an aralkyloxy group optionally substituted with substituent D, R40 (CH2) pU- (where p, R40 and U are as defined above), R41R42N. -(Where R41 and R42 are as defined above), R43-L4- (where R43 and L4 are as defined above), R44C (= ) O- (where R44 has the same meaning as described above), or R47R48C = NO- (where R47 and R48 have the same meaning as described above) [1] to [3], [ 5] The compound according to any one of [18] or a salt thereof.

[20] The substituent D2 is
Cyano group, vinyl group, 1-propenyl group, allyl group, ethynyl group, 1-propynyl group, propargyl group, vinyloxy group, 1-propenyloxy group, allyloxy group, propargyloxy group, 2-butynyloxy group, 3-butynyloxy group Methoxymethoxy group, ethoxymethoxy group, methoxyethoxy group, methoxypropyloxy group, acetonitrileoxy group, 3-propanenitrileoxy group, cyclopropylmethoxy group, cyclopentylmethoxy group, cyclopropylethoxy group, 1H-pyrazol-1-yl Group, 1H-1,2,4-triazol-1-yl group, phenoxy group, (4-methoxy) phenoxy group, benzyloxy group, phenethyloxy group, (tetrahydrofuran-2-yl) methoxy group, (1,3 -Dioxolan-2-yl Methoxy, (dimethylamino) ethoxy, (dimethylamino) propyloxy, (methylthio) methoxy, (methylthio) ethoxy, (methylthio) propyl, methylamino, ethylamino, dimethylamino, ethylmethyl Amino group, diethylamino group, methylthio group, methanesulfinyl group, methanesulfonyl group, acetyloxy group, methoxyacetyloxy group, cyanoacetyloxy group, difluoroacetyloxy group, trifluoroacetyloxy group, methoxycarbonyloxy group, ethoxycarbonyloxy group Group, aminocarbonyloxy group, dimethylaminocarbonyloxy group, ethylmethylaminocarbonyloxy group, diethylaminocarbonyloxy group, dimethyliminooxy group, ethylmethyliminooxy Or an diethyl imino group, [1] to [3], [5] the compound according to any one of - [18] or a salt thereof.

[21] The substituent D2 is
Cyano group, ethynyl group, allyloxy group, propargyloxy group, methoxymethoxy group, methoxyethoxy group, methoxypropyloxy group, acetonitrileoxy group, cyclopropylmethoxy group, 1H-pyrazol-1-yl group, 1H-1,2,2 4-triazol-1-yl group, (4-methoxy) phenoxy group, benzyloxy group, (tetrahydrofuran-2-yl) methoxy group, (1,3-dioxolan-2-yl) methoxy group, (dimethylamino) ethoxy Represents a group, (dimethylamino) propyloxy group, (methylthio) methoxy group, methylamino group, dimethylamino group, methylthio group, acetyloxy group, or dimethyliminooxy group, [1] to [3], [5] Or the salt thereof according to any one of [18] to [18].

[22] Y is
Represents a phenyl group, wherein the phenyl group has a substituent D substituted at the ortho-position, a substituent D1 independently substituted with 0 to 3 as appropriate, and a substituent D2 independently substituted with 1 to 4 as appropriate. The compound according to any one of [1] to [3] and [5] to [21], or a salt thereof, which is substituted.

の部分構造を表す、［１］〜［３］、［５］〜［２１］のいずれか１つに記載の化合物、またはその塩。[23] Y is represented by the formula (a-1)

The compound according to any one of [1] to [3] and [5] to [21], or a salt thereof, which represents a partial structure of

[24] Y is
2,6-difluoro-4- (dimethylamino) ethoxy-phenyl group,
2,6-difluoro-4- (dimethylamino) propyloxy-phenyl group,
2,6-difluoro-4-acetonitrileoxy-phenyl group,
2,6-difluoro-4-propargyloxy-phenyl group,
2,6-difluoro-4-methoxymethoxy-phenyl group,
2,6-difluoro-4-methoxyethoxy-phenyl group,
2,6-difluoro-4-allyloxy-phenyl group,
2,6-difluoro-4-methoxypropyloxy-phenyl group,
2,6-difluoro-4-methylthiomethoxy-phenyl group,
2,6-difluoro-4-ethynyl-phenyl group,
2,6-difluoro-4- (tetrahydrofuran-2-yl) methoxy-phenyl group,
2,6-difluoro-4- (1,3-dioxolan-2-yl) methoxy-phenyl group,
2,6-difluoro-4-methylthio-phenyl group,
2,6-difluoro-4- (1H-pyrazol-1-yl) -phenyl group,
2,6-difluoro-4- (1H-1,2,4-triazol-1-yl) -phenyl group,
2,6-difluoro-4-cyclopropylmethoxy-phenyl group,
2,6-difluoro-4-acetyloxy-phenyl group,
2,6-difluoro-4-dimethyliminooxy-phenyl group,
2,6-difluoro-4-benzyloxy-phenyl group,
2,6-difluoro-4- (4-methoxyphenoxy) -phenyl group,
2,6-difluoro-4-cyano-phenyl group,
2,6-difluoro-4-methylamino-phenyl group,
Or the compound according to any one of [1] to [3] and [5] to [13], which represents a 2,6-difluoro-4-dimethylamino-phenyl group, or a salt thereof.

[25] X is
The compound according to any one of [1] to [3] and [5] to [24], which is an oxygen atom, or a salt thereof.

[26] X is
The compound according to any one of [1] to [3] and [5] to [24], which is a sulfur atom, or a salt thereof.

[27] The bond including the broken line portion is
The compound according to any one of [1] to [3] and [5] to [26], which is a double bond, or a salt thereof.

[28] The bond including the broken line portion is
The compound according to any one of [1] to [3] and [5] to [26], which is a single bond, or a salt thereof.

[29] A pest control agent for agricultural and horticultural use, comprising the compound according to [1] to [3] or [5] to [28] or a salt thereof as an active ingredient.

[30] A fungicide for agricultural and horticultural use containing the compound or salt thereof according to [1] to [3] or [5] to [28] as an active ingredient.

[31] A method for controlling plant diseases, comprising applying the pesticidal composition for agricultural and horticultural use according to [29] to a plant, a plant seed, or a soil in which the plant is grown.

[32] A method for controlling plant diseases, which comprises applying the agricultural and horticultural fungicide according to [30] to a plant, a plant seed, or a soil in which the plant is grown.

[33] Use of the compound according to any one of [1] to [3] and [5] to [28] as a pesticide for agricultural and horticultural use.

[34] Use of the compound according to any one of [1] to [3] and [5] to [28] as an agricultural and horticultural fungicide.

  ADVANTAGE OF THE INVENTION According to this invention, the novel compound effective as an agricultural and horticultural fungicide can be provided.

  Hereinafter, embodiments for carrying out the present invention will be described in detail.

  Each term used in the claims and the specification is defined according to a definition generally used in the technical field, unless otherwise specified.

Abbreviations used in this specification are described below.
DMF: N, N-dimethylformamide, DMSO: dimethylsulfoxide, THF: tetrahydrofuran, Me: methyl group, Et: ethyl group, Pr: propyl group, Bu: butyl group, Pentyl: pentyl group, Hexyl: hexyl group, Ac: Acetyl group, Ph: phenyl group, Py: pyridyl group, i: iso, sec: secondary, t: tertiary, c: cyclo, =: double bond, ≡: triple bond. In the columns of the table, a single “-” means no substitution, and Pr, Bu, Pentyl, and Hexyl mean normal when there is no prefix.

  Hereinafter, definitions of terms used in the present specification will be described.

  The description Cx-Cy indicates that it has x to y carbon atoms.

  The term "optionally substituted" means substituted or unsubstituted. In using this term, when the number of substituents is not specified, it indicates that the number of substituents is 1.

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

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

  The C1 to C6 haloalkyl group means a C1 to C6 alkyl group in which a hydrogen atom is arbitrarily 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 substitution is not particularly limited as long as it can be present as a substituent. Specific examples of C1 to C6 haloalkyl groups include monofluoromethyl, difluoromethyl, trifluoromethyl, monochloromethyl, monobromomethyl, monoiodomethyl, chlorodifluoromethyl, bromodifluoromethyl, -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-heptafluoro-pentyl group, undecyl decafluoropentyl, 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 to C6 alkenyl group refers to a linear or branched unsaturated hydrocarbon group having one or more double bonds. When there is a geometric isomer, only one of the E-form and the Z-form, or a mixture of the E-form and the Z-form in an arbitrary ratio is used, and if it is in the range of the specified number of carbon atoms, it is not particularly limited. Never. Specific examples of the C2 to C6 alkenyl groups include vinyl, 1-propenyl, allyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, and 3-pentenyl. Group, 4-pentenyl group, 3-methyl-2-butenyl group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group, 4-methyl-3-pentenyl group, And a 3-methyl-2-pentenyl group.

  The C2 to C6 haloalkenyl group means a C2 to C6 alkenyl group in which a hydrogen atom is arbitrarily substituted by 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 substitution is not particularly limited as long as it can be present as a substituent. Specific examples of the C2 to C6 haloalkenyl group include a 2-fluorovinyl group, a 2,2-difluorovinyl group, a 2,2-dichlorovinyl group, a 3-fluoroallyl group, a 3,3-difluoroallyl group, Examples thereof include a 3-dichloroallyl group, a 4,4-difluoro-3-butenyl group, a 5,5-difluoro-4-pentenyl group, and a 6,6-difluoro-5-hexenyl group.

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

  The C2 to C6 haloalkynyl group refers to a C2 to C6 alkynyl group in which a hydrogen atom is arbitrarily substituted by 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 substitution is not particularly limited as long as it can be present as a substituent. Specific examples of the C2 to C6 haloalkynyl groups include 2-fluoroethynyl, 2-chloroethynyl, 2-bromoethynyl, 2-iodoethynyl, 3,3-difluoro-1-propynyl, and 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- And a trifluoro-4-hexynyl group.

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

  The C1 to C6 haloalkoxy group means a C1 to C6 alkoxy group in which a hydrogen atom is arbitrarily substituted by 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 substitution is not particularly limited as long as it can be present as a substituent. Specific examples of the C1-C6 alkoxy group include a difluoromethoxy group, a trifluoromethoxy group, a chlorodifluoromethoxy group, a bromodifluoromethoxy group, a 2-fluoroethoxy group, a 2,2-difluoroethoxy group, a 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-trifluoro Propyloxy 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, c Decafluoropentyl group, tridecafluorohexyl group, and the like.

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

  The C2-C6 alkenyloxy group refers to the above-mentioned C2-C6 alkenyl group bonded via an oxygen atom. In addition, when there is a geometric isomer, only one of the E-form or the Z-form, or a mixture of the E-form and the Z-form in an arbitrary ratio is used. Never. Specific examples of C2 to C6 alkenyloxy groups include vinyloxy, 1-propenyloxy, allyloxy, 1-butenyloxy, 2-butenyloxy, 3-butenyloxy, 1-pentenyloxy, and 2-pentenyloxy. , 3-pentenyloxy, 4-pentenyloxy, 3-methyl-2-butenyloxy, 1-hexenyloxy, 2-hexenyloxy, 3-hexenyloxy, 4-hexenyloxy, 5-hexenyloxy Group, 4-methyl-3-pentenyloxy group, 3-methyl-2-pentenyloxy group and the like.

  The C2 to C6 haloalkenyloxy group refers to a C2 to C6 alkenyloxy group in which a hydrogen atom is arbitrarily 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 substitution is not particularly limited as long as it can be present as a substituent. Specific examples of the C2 to C6 haloalkenyloxy group include a 2-fluorovinyloxy group, a 2,2-difluorovinyloxy group, a 2,2-dichlorovinyloxy group, a 3-fluoroallyloxy group, and a 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. Can be

  The C3-C6 alkynyloxy group means a C3-C6 alkynyl group in which the C3-C6 alkynyl group is bonded via an oxygen atom. Specific examples of the C3-C6 alkynyloxy group 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 means a C3-C6 alkynyloxy group in which a hydrogen atom is arbitrarily 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 substitution is not particularly limited as long as it can be present as a substituent. Specific examples of the C3 to C6 haloalkynyloxy group include a 1,1-difluoro-2-propynyloxy group, a 4,4-difluoro-2-butynyloxy group, and a 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- Trifluoroacetic 4- hexynyloxy group.

  The C2 to C6 alkoxyalkoxy group is a C1 to C6 alkoxy group in which a hydrogen atom in the C1 to C5 alkoxy group is arbitrarily substituted with one or more C1 to C5 alkoxy groups. Represents There is no particular limitation as long as the sum of the carbon numbers is within the specified carbon number range. Specific examples of C2 to C6 alkoxyalkoxy groups include methoxymethoxy, ethoxymethoxy, propyloxymethoxy, isopropyloxymethoxy, methoxyethoxy, ethoxyethoxy, propyloxyethoxy, isopropyloxyethoxy, and methoxypropyl. Examples thereof include an oxy group, an ethoxypropyloxy group, a propyloxypropyloxy group, and an isopropyloxypropyloxy group.

  The C2 to C6 cyanoalkoxy group means a C1 to C6 alkoxy group in which a hydrogen atom in the C1 to C5 alkoxy group is arbitrarily substituted with one or two or more cyano groups. There is no particular limitation as long as the sum of the carbon numbers is within the specified carbon number range. Specific examples of the C2 to C6 cyanoalkoxy group include an acetonitrileoxy group, a 3-propanenitrileoxy group, a 4-butanenitrileoxy group, a 5-pentanenitrileoxy group, a 6-hexanenitrileoxy group, and a 2-propanenitrileoxy group. , 2-butanenitrileoxy group, 2-pentanenitrileoxy group, 2-methylpropanenitrile-3-oxy group, and the like.

  The C4-C9 cycloalkylalkoxy group means that one or two or more of the above-mentioned C3-C8 cycloalkyl groups in which the hydrogen atom in the C1-C5 alkoxy group among the above-mentioned C1-C6 alkoxy groups is arbitrary. Represents those substituted with There is no particular limitation as long as the sum of the carbon numbers is within the specified carbon number range. Specific examples of the C4-C9 cycloalkylalkoxy group include cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cycloheptylmethoxy, cyclooctylmethoxy, cyclopropylethoxy, cyclobutylethoxy, and cyclobutylethoxy. Group, cyclopentylethoxy group, cyclohexylethoxy group, cyclopropylpropanyloxy, cyclobutylpropanyloxy, cyclopentylpropanyloxy, cyclohexylpropanyloxy and the like.

  The aryl group represents a cyclic aromatic substituent composed of a hydrogen atom and a carbon atom. Specific examples of the aryl group include a phenyl group and a naphthyl group.

  The heteroaryl group is selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom, and represents a cyclic aromatic substituent containing at least one hetero atom as a ring constituent atom. Specific examples of the heteroaryl group, pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, tetrazinyl group, thienyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, furyl group, pyrrolyl group, imidazolyl group, pyrazolyl group, Examples include an oxazolyl group, an isoxazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group, and a tetrazolyl group.

  An aryloxy group refers to the above-mentioned aryl group bonded via an oxygen atom. Specific examples of the aryloxy group include a phenoxy group and a naphthyloxy group.

  The heteroaryloxy group refers to the above-mentioned heteroaryl group bonded via an oxygen atom. Specific examples of the heteroaryloxy group include a pyridyloxy group, a pyridazinyloxy group, a pyrimidinyloxy group, a pyrazinyloxy group, a triazinyloxy group, a tetrazinyloxy group, a thienyloxy group, a thiazolyloxy group, and an isothiazolyloxy group. Group, thiadiazolyloxy group, furyloxy group, pyrrolyloxy group, imidazolyloxy group, pyrazolyloxy group, oxazolyloxy group, isoxazolyloxy group, triazolyloxy group, oxadiazolyloxy group, thiadiazolyl group An oxy group, a tetrazolyloxy group and the like can be mentioned.

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

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

The pyridone compound of the present invention includes a compound represented by the following formula (1) and a salt thereof.

  Hereinafter, equation (1) will be described.

  R1 in the 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, or a C3 to C8 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, 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 substituent A C2-C6 alkenyloxy group optionally substituted with A, a C2-C6 haloalkenyloxy group, a C3-C6 alkynyloxy group optionally substituted with substituent A, C3-C Halo alkynyloxy group, or R10R11N- (wherein, R10, and R11 are each independent represent. A hydrogen atom or an alkyl group C1 -C6,) represents a.

Among them, R1 is a cyano group, a C1 to C6 alkyl group optionally substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group optionally substituted with a substituent A, A C2-C6 alkenyl group optionally substituted with a group A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group optionally substituted with a substituent A, or R10R11N- (where R10 and R11 has the same meaning as described above.),
In particular, a C1-C6 alkyl group which may be appropriately substituted with the substituent A, or a C1-C6 haloalkyl group is preferable,
Further, a C1-C6 alkyl group is preferred.

The “substituent A” in the formula (1) includes a hydroxyl group, a cyano group, a C3 to C8 cycloalkyl group, a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group, and R12R13N. -(Where R12 and R13 are each independently a hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group, or R12 and R13 are And a nitrogen atom to be bonded to form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, a piperidinyl group, a homopiperidinyl group, or an azocanyl group.) And R14-L1- (where R14 is represents an alkyl group or a haloalkyl group of C1 -C6, a C1 -C6, L1 is, S, SO, or SO ₂ Represents at least one selected from the group consisting of:

Among them, the substituent A is preferably a cyano group, a C1 to C6 alkoxy group, or R14-L1- (where R14 and L1 have the same meanings as described above).
Particularly, a cyano group or a C1 to C6 alkoxy group is preferable.

Preferred specific examples of the substituent A include a hydroxyl group; a cyano group;
As a C3-C8 cycloalkyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group;
A C1-C6 alkoxy group such as a methoxy group, an ethoxy group, a propyloxy group, and an isopropyloxy group;
As C1 to C6 haloalkoxy groups, difluoromethoxy, trifluoromethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 3,3-difluoropropyloxy, and 3,3 , 3-trifluoropropyloxy group;
A C3-C8 cycloalkoxy group such as a cyclopropyloxy group, a cyclobutoxy group, a cyclopentyloxy group, and a cyclohexyloxy group;
R12R13N- (where R12 and R13 have the same meanings as described above), such as an amino group, a dimethylamino group, an ethylmethylamino group, and a diethylamino group;
And R14-L1- (where R14 and L1 have the same meanings as described above) include a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, a trifluoromethanesulfinyl group, and a trifluoromethanesulfonyl group. No.

More preferred specific examples of the substituent A include a hydroxyl group; a cyano group;
A C3-C8 cycloalkyl group such as a cyclopropyl group and a cyclobutyl group;
A methoxy group and an ethoxy group as the C1-C6 alkoxy group;
A C1-C6 haloalkoxy group such as a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, and a 2,2,2-trifluoroethoxy group;
A C3-C8 cycloalkoxy group such as a cyclopropyloxy group and a cyclobutoxy group;
R12R13N- (where R12 and R13 have the same meanings as described above), such as a dimethylamino group, an ethylmethylamino group, and a diethylamino group;
And R14-L1- (where R14 and L1 are as defined above), include a methylthio group, a methanesulfinyl group, and a methanesulfonyl group.

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

  The C1 to C6 alkyl group of the “C1 to C6 alkyl group optionally substituted with the substituent A” for R1 in the formula (1) has the same meaning as described above, and is preferably a methyl group or an ethyl group. Propyl group, isopropyl group, butyl group, or isobutyl group, more preferably, methyl group, ethyl group, or propyl group, and particularly preferably methyl group or ethyl group. When it has the substituent A, the hydrogen atom in the C1-C6 alkyl group is optionally substituted by the substituent A.

  The “C1 to C6 haloalkyl group” for R1 in the formula (1) is as defined above, and is preferably a 2-fluoroethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoro group. An ethyl group, a 3,3-difluoropropyl group, or a 3,3,3-trifluoropropyl group, more preferably a 2-fluoroethyl group, a 2,2-difluoroethyl group, or a 2,2,2- It is a trifluoroethyl group, particularly preferably a 2,2-difluoroethyl group or a 2,2,2-trifluoroethyl group.

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

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

  The “C2 to C6 haloalkenyl group” for R1 in the formula (1) is as defined above, and is 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 to C6 alkynyl group of the "C2 to C6 alkynyl group optionally substituted with the substituent A" for R1 in the formula (1) is the same as defined above, and is preferably a propargyl group, It is a butynyl group or a 3-butynyl group, and more preferably a propargyl group. When it has the substituent A, the hydrogen atom in the C2 to C6 alkynyl group is optionally substituted by the substituent A.

  The "C2-C6 haloalkynyl group" for R1 in the formula (1) is as defined above, and preferably is a 4,4-difluoro-2-butynyl group, 4-chloro-4,4-difluoro- A 2-butynyl group, a 4-bromo-4,4-difluoro-2-butynyl group, or a 4,4,4-trifluoro-2-butynyl group, and more preferably 4,4-difluoro-2-butynyl Or a 4,4,4-trifluoro-2-butynyl group.

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

  The “C1 to C6 haloalkoxy group” for R1 in the formula (1) is as defined above, and is preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2 A 2-trifluoroethoxy group, a 3,3-difluoropropyloxy group, or a 3,3,3-trifluoropropyloxy group, more preferably a difluoromethoxy group, a trifluoromethoxy group, or a 2,2-difluoroethoxy group; Or 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 the formula (1) has the same meaning as defined above, and is preferably cyclopropyloxy. A cyclobutoxy group, a cyclopentyloxy group or a cyclohexyloxy group, and more preferably a cyclopropyloxy group or a cyclobutoxy group. When it has the substituent A, the hydrogen atom in the C3-C8 cycloalkoxy group is optionally substituted by the substituent A.

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

  The “C2 to C6 haloalkenyloxy group” for R1 in the formula (1) has the same meaning as the above definition, and is preferably a 2-fluorovinyloxy group, a 2,2-difluorovinyloxy group, a 3-fluoro 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 of the "C3-C6 alkynyloxy group optionally substituted with the substituent A" for R1 in the formula (1) has the same meaning as the above definition, and is preferably a propargyloxy group , A 2-butynyloxy group or a 3-butynyloxy group, and more preferably a propargyloxy group. When it has the substituent A, the hydrogen atom in the C3-C6 alkynyloxy group is optionally substituted by the substituent A.

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

  The C1 to C6 alkyl group of "R10R11N-" in R1 of the formula (1) (where R10 and R11 are each independently a hydrogen atom or a C1 to C6 alkyl group) is as described above. Synonymous with the definition. "R10R11N-" preferably includes an amino group, a dimethylamino group, an ethylmethylamino group, and a diethylamino group, and more preferably includes an amino group and a dimethylamino group.

R2 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, and a C3 to C3 optionally substituted with a substituent B. C8 cycloalkyl group, C2-C6 alkenyl group optionally substituted with substituent B, C2-C6 haloalkenyl group, C2-C6 alkynyl group optionally substituted with substituent B, C2- A C6 haloalkynyl group, a C1 to C6 alkoxy group optionally substituted with a substituent B, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group optionally substituted with a substituent B, A C2-C6 alkenyloxy group optionally substituted with group B, a C2-C6 haloalkenyloxy group, a C3-C6 alkynyloxy group optionally substituted with substituent B Group, a C3-C6 haloalkynyloxy group, R20C (= O)-(where R20 is a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 An alkoxy group, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group, or R21R22N- (wherein R21 and R22 are each independently and may be appropriately substituted with a hydrogen atom or a substituent B1. Represents a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, or a C3 to C8 cycloalkyl group, or R21 and R22 together with a bonding nitrogen atom form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group; , A piperidinyl group, a homopiperidinyl group, or an azocanyl group.) 0C (= O) O- (where R20 has the same meaning as described above), R21R22N- (where R21 and R22 have the same meaning as above), R23-L2- (where R23 is the same as above). represents an alkyl group or a haloalkyl group of C1 -C6, a C1 -C6, L2 is S, SO or an _{SO 2), R24C (= O} ) N (R25), -. ( here, R24 A hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or R21R22N- (wherein, R21 and R22 have the same meanings as described above), and R25 represents a hydrogen atom, a C1 to C6 alkyl group optionally substituted with a substituent B1, a C1 to C2 It represents a haloalkyl group or a cycloalkyl group of C3 -C8,. ) Or a 3- to 6-membered ring group containing 1 to 2 oxygen atoms.

Among them, R2 is a hydroxyl group, 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 optionally substituted with a substituent B. An alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group optionally substituted with a substituent B, a C2-C6 alkenyloxy group optionally substituted with a substituent B, a substituent B A C3-C6 alkynyloxy group, R20C (= O) O- (where R20 is as defined above), or R23-L2- (where R23 and L2 are Is the same as defined above).
Particularly, a halogen atom, a C1 to C6 alkyl group optionally substituted with a substituent B, a C1 to C6 alkoxy group optionally substituted with a substituent B, or R23-L2- (where R23 and L2 has the same meaning as described above.
Further, a halogen atom, a C1 to C6 alkoxy group, or R23-L2- (where R23 and L2 have the same meanings as described above) are preferable.

The “substituent B” in the formula (1) includes 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 To C6 alkoxyalkoxy groups, R21R22N- (where R21 and R22 have the same meanings as described above), R23-L2- (where R23 and L2 have the same meanings as described above), and R26R27R28Si- ( Here, R26, R27, and R28 are each independently and represent a C1 to C6 alkyl group.), R26R27R28Si— (CH ₂ ) s—O— (where s is an integer of 1 to 3) Wherein R26, R27, and R28 have the same meanings as described above), R20C (（O)-(where R20 has the same meaning as the above R20), and It represents at least one member selected from the group consisting of 3-6 membered group ring containing to 2 oxygen atoms.

Among them, the substituent B is a cyano group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C2-C6 alkoxyalkoxy group, R23-L2- (where R23 and L2 are as defined above). .), R26R27R28Si- (wherein, R26, R27, and R28 have the same meanings as defined _{above.), R26R27R28Si- (CH 2)} s-O- ( wherein, s, R26, R27, and R28 are the R20C (= O)-(where R20 has the same meaning as described above), or a 3- to 6-membered ring group containing 1 or 2 oxygen atoms,
Particularly, a cyano group or a C1 to C6 alkoxy group is preferable.

Preferred specific examples of the substituent B include a hydroxyl group; a cyano group;
As a C3-C8 cycloalkyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group;
A C1-C6 alkoxy group such as a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group, and an isobutoxy group;
As C1 to C6 haloalkoxy groups, difluoromethoxy, trifluoromethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 3,3-difluoropropyloxy, and 3,3 , 3-trifluoropropyloxy group;
A C3-C8 cycloalkoxy group such as a cyclopropyloxy group, a cyclobutoxy group, a cyclopentyloxy group, and a cyclohexyloxy group;
A C2-C6 alkoxyalkoxy group such as a methoxymethoxy group, an ethoxymethoxy group, a methoxyethoxy group, an ethoxyethoxy group, and a methoxypropyloxy group;
R21R22N- (where R21 and R22 have the same meanings as described above), such as an amino group, a dimethylamino group, an ethylmethylamino group, a diethylamino group, a pyrrolidinyl group, and a piperidinyl group;
R23-L2- (where R23 and L2 are as defined above), such as a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, a trifluoromethanesulfinyl group, and a trifluoromethanesulfonyl group;
R26R27R28Si- (where R26, R27 and R28 have the same meanings as described above), as a trimethylsilyl group and a triethylsilyl group;
_{R26R27R28Si- (CH 2) s-O-} ( wherein, s, R26, R27, and R28 are the same as defined above.) As a 2- (trimethylsilyl) ethoxy, and 2- (triethylsilyl) ethoxy ;
R20C (= O)-(where R20 has the same meaning as described above) as an acetyl group, a propionyl group, a difluoroacetyl group, a trifluoroacetyl group, a cyclopropanecarbonyl group, a methoxycarbonyl group, an ethoxycarbonyl group, 2,2-difluoroethoxycarbonyl group, 3,3,3-trifluoropropyloxycarbonyl group, cyclopropyloxycarbonyl group, aminocarbonyl group, dimethylaminocarbonyl group, ethylmethylaminocarbonyl group, diethylaminocarbonyl group, pyrrolidinyl A carbonyl group, and a piperidinylcarbonyl group;
In addition, examples of the 3- to 6-membered ring group containing one or two oxygen atoms include an oxolanyl group, an oxanyl group, a 1,3-dioxolanyl group, and a 1,3-dioxanyl group.

More preferred specific examples of the substituent B include a hydroxyl group; a cyano group;
A C3-C8 cycloalkyl group such as a cyclopropyl group and a cyclobutyl group;
A methoxy group and an ethoxy group as the C1-C6 alkoxy group;
A C1-C6 haloalkoxy group such as a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, and a 2,2,2-trifluoroethoxy group;
A C3-C8 cycloalkoxy group such as a cyclopropyloxy group and a cyclobutoxy group;
A C2-C6 alkoxyalkoxy group such as a methoxymethoxy group, an ethoxymethoxy group, a methoxyethoxy group, and an ethoxyethoxy group;
R21R22N- (where R21 and R22 are as defined above), such as a dimethylamino group, an ethylmethylamino group, and a diethylamino group;
R23-L2- (where R23 and L2 have the same meaning as described above); a methylthio group, a methanesulfinyl group, and a methanesulfonyl group;
R26R27R28Si- (where R26, R27 and R28 have the same meanings as described above), as a trimethylsilyl group;
_{R26R27R28Si- (CH 2) s-O-} (. Here, s, R26, R27, and R28 have the same meanings as defined above) as, 2- (trimethylsilyl) ethoxy group;
R20C (= O)-(where R20 has the same meaning as described above) as an acetyl group, difluoroacetyl group, trifluoroacetyl group, methoxycarbonyl group, ethoxycarbonyl group, aminocarbonyl group, dimethylaminocarbonyl group , An ethylmethylaminocarbonyl group, and a diethylaminocarbonyl group;
In addition, examples of the 3- to 6-membered ring group containing one or two oxygen atoms include a 1,3-dioxolanyl group and a 1,3-dioxanyl group.

  The “substituent B1” in the formula (1) is at least one selected from the group consisting of a cyano group, a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group, and a C3 to C8 cycloalkoxy group. Represent. Among them, the substituent B1 is preferably a cyano group or a C1 to C6 alkoxy group.

Preferred specific examples of the substituent B1 include a cyano group;
A C1-C6 alkoxy group such as a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group, and an isobutoxy group;
As C1 to C6 haloalkoxy groups, difluoromethoxy, trifluoromethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 3,3-difluoropropyloxy, and 3,3 , 3-trifluoropropyloxy group;
And C3-C8 cycloalkoxy groups include cyclopropyloxy, cyclobutoxy, cyclopentyloxy, and cyclohexyloxy groups.

As more preferred specific examples of the substituent B1, a cyano group;
A methoxy group and an ethoxy group as the C1-C6 alkoxy group;
A C1-C6 haloalkoxy group such as a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, and a 2,2,2-trifluoroethoxy group;
And as the C3-C8 cycloalkoxy group, a cyclopropyloxy group and a cyclobutoxy group can be mentioned.

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

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

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

  The “C1 to C6 haloalkyl group” for R2 in the formula (1) is as defined above, and is preferably a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, a 2,2,2 -Trifluoroethyl group, 3,3-difluoropropyl group, or 3,3,3-trifluoropropyl group, 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 substituent B" in R2 of the formula (1) has the same meaning as the above definition, and is preferably a cyclopropyl group. , A cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, and more preferably a cyclopropyl group or a cyclobutyl group. When it has the substituent B, the hydrogen atom in the C3-C8 cycloalkyl group is optionally substituted by the substituent B.

  The C2 to C6 alkenyl group of the "C2 to C6 alkenyl group optionally substituted with the substituent B" for R2 in the formula (1) has the same meaning as described above, and is preferably a vinyl group, 1- It is a propenyl group, an allyl group, a 1-butenyl group, a 2-butenyl group or a 3-butenyl group, more preferably a vinyl group, a 1-propenyl group or an allyl group. When the compound has the substituent B, the hydrogen atom in the C2 to C6 alkenyl group is optionally substituted with the substituent B.

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

  The C2 to C6 alkynyl group of the "C2 to C6 alkynyl group optionally substituted with the substituent B" in R2 of the formula (1) has the same meaning as described above, and is preferably an ethynyl group, 1- It is a propynyl group, a propargyl group, a 1-butynyl group, a 2-butynyl group or a 3-butynyl group, and more preferably an ethynyl group, a 1-propynyl group or a propargyl group. When it has the substituent B, the hydrogen atom in the C2 to C6 alkynyl group is optionally substituted by the substituent B.

  The “C2 to C6 haloalkynyl group” for R2 in the formula (1) is as defined above, and is preferably a 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, and more preferably a 3,3-difluoro-1-propynyl group or a 3,3,3-trifluoro-1-propynyl group.

  The C1 to C6 alkoxy group of the "C1 to C6 alkoxy group optionally substituted with the substituent B" for R2 in the formula (1) has the same meaning as described above, and is preferably a methoxy group or an ethoxy group. , Propyloxy group, isopropyloxy group, butoxy group, isobutoxy group, or pentyloxy group, more preferably methoxy group, ethoxy group, propyloxy group, or isopropyloxy group, particularly preferably methoxy group is there. When it has the substituent B, the hydrogen atom in the C1-C6 alkoxy group is optionally substituted by the substituent B.

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

  The C3-C8 cycloalkoxy group of the "C3-C8 cycloalkoxy group optionally substituted with substituent B" for R2 in formula (1) has the same meaning as defined above, and is preferably cyclopropyloxy. A cyclobutoxy group, a cyclopentyloxy group or a cyclohexyloxy group, and more preferably a cyclopropyloxy group or a cyclobutoxy group. When it has the substituent B, the hydrogen atom in the C3-C8 cycloalkoxy group is optionally substituted by the substituent B.

  The C2 to C6 alkenyloxy group of the “C2 to C6 alkenyloxy group optionally substituted with the substituent B” for R2 in the formula (1) has the same meaning as described above, and is preferably a vinyloxy group, It is a 1-propenyloxy group, an allyloxy group, a 1-butenyloxy group, a 2-butenyloxy group, or a 3-butenyloxy group, and more preferably a vinyloxy group, a 1-propenyloxy group, or an allyloxy group. When it has the substituent B, the hydrogen atom in the C2-C6 alkenyloxy group is optionally substituted by the substituent B.

  The “C2 to C6 haloalkenyloxy group” for R2 in the formula (1) is as defined above, and is preferably a 2-fluorovinyloxy group, a 2,2-difluorovinyloxy group, a 2,2- A dichlorovinyloxy group, a 3-fluoroallyloxy group, a 3,3-difluoroallyloxy group, or a 3,3-dichloroallyloxy group, more preferably a 2-fluorovinyloxy group or a 2,2-difluoro It is a vinyloxy group.

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

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

  "R20C (= O)-" in R2 of the formula (1) (where R20 is a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group) , A C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group, or R21R22N- (wherein R21 and R22 are each independently a hydrogen atom or a C1 to C22 optionally substituted with a substituent B1. Represents an alkyl group of C6, a haloalkyl group of C1 to C6, or a cycloalkyl group of C3 to C8, or R21 and R22 together with a bonding nitrogen atom form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, a piperidinyl group; Group, a homopiperidinyl group, or an azocanyl group.). As synonymous. As "R20C (= O)-", preferably, an acetyl group, a propionyl group, a difluoroacetyl group, a trifluoroacetyl group, a cyclopropanecarbonyl group, a methoxycarbonyl group, an ethoxycarbonyl group, a 2,2-difluoroethoxycarbonyl group, 2,2,2-trifluoroethoxycarbonyl group, cyclopropyloxycarbonyl group, aminocarbonyl group, dimethylaminocarbonyl group, ethylmethylaminocarbonyl group, diethylaminocarbonyl group, pyrrolidinylcarbonyl group, and piperidinylcarbonyl group And more preferably acetyl, difluoroacetyl, trifluoroacetyl, methoxycarbonyl, ethoxycarbonyl, aminocarbonyl, dimethylaminocarbonyl, ethylmethyl Bruno carbonyl group, and a diethylamino group.

  R20 of "R20C (= O) O-" in R2 of the formula (1) is as defined above. As "R20C (= O) O-", preferably, an acetyloxy group, a propionyloxy group, a difluoroacetyloxy group, a trifluoroacetyloxy group, a cyclopropanecarbonyloxy group, a methoxycarbonyloxy group, an ethoxycarbonyloxy group, , 2-Difluoroethoxycarbonyloxy group, 2,2,2-trifluoroethoxycarbonyloxy group, cyclopropyloxycarbonyloxy group, aminocarbonyloxy group, dimethylaminocarbonyloxy group, ethylmethylaminocarbonyloxy group, diethylaminocarbonyloxy Group, a pyrrolidinylcarbonyloxy group, and a piperidinylcarbonyloxy group, and more preferably, an acetyloxy group, a difluoroacetyloxy group, and a trifluoroacetyloxy group. Shi group, methoxycarbonyloxy group, ethoxycarbonyloxy group, aminocarbonyl group, dimethylaminocarbonyl group, ethylmethylamino carbonyloxy groups, and diethylamino carbonyl group.

  R21 and R22 of "R21R22N-" in R2 of the formula (1) are as defined above. "R21R22N-" preferably includes an amino group, a dimethylamino group, an ethylmethylamino group, a diethylamino group, a pyrrolidinyl group, and a piperidinyl group, and more preferably a dimethylamino group, an ethylmethylamino group, and a diethylamino group. Is mentioned.

"R23-L2 -" in R2 of formula (1) (wherein, R23 represents an alkyl group or a haloalkyl group of C1 -C6, a C1 -C6, L2 represents S, SO, or SO _2. Each term in ()) is synonymous with the above definition. As “R23-L2-”, preferably, a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, a trifluoromethanesulfinyl group, a trifluoromethanesulfonyl group, a (chloromethyl) thio group, and a (chloromethane) sulfinyl group Or a (chloromethane) sulfonyl group, more preferably a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a (chloromethyl) thio group, a (chloromethane) sulfinyl group, or a (chloromethane) sulfonyl group. And particularly preferably a methylthio group.

  "R24C (= O) N (R25)-" in R2 of the formula (1) (where R24 is a hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group) , A C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or R21R22N- (where R21 and R22 have the same meanings as described above), and R25 represents hydrogen. Atom, a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, or a C3 to C8 cycloalkyl group which may be appropriately substituted with the substituent B1.) Are as defined above. . R24 is preferably a hydrogen atom, a methyl group, an ethyl group, a difluoromethyl group, a trifluoromethyl group, a cyclopropyl group, a methoxy group, an ethoxy group, a 2,2-difluoroethoxy, a 2,2,2-trifluoroethoxy. Group, cyclopropyloxy group, amino group, dimethylamino group, ethylmethylamino group, diethylamino group, pyrrolidinyl group, and piperidinyl group, more preferably, hydrogen atom, methyl group, difluoromethyl group, trifluoromethyl group Methoxy, ethoxy, amino, dimethylamino, ethylmethylamino, and diethylamino groups. Further, as R25, preferably, a hydrogen atom, a methyl group, an ethyl group, a propyl group, a methoxymethyl group, an ethoxymethyl group, a methoxyethyl group, an ethoxyethyl group, a cyanomethyl group, a 2-cyanoethyl group, and a 2,2-difluoroethyl Group, 2,2,2-trifluoroethyl group, and cyclopropyl group, more preferably, hydrogen atom, methyl group, ethyl group, methoxymethyl group, ethoxymethyl group, methoxyethyl group, ethoxyethyl group, Examples include a cyanomethyl group, a 2,2-difluoroethyl group, and a 2,2,2-trifluoroethyl group.

  The “3- to 6-membered ring group containing 1 or 2 oxygen atoms” in R 2 of the formula (1) is as defined above, and is preferably an oxolanyl group, an oxanyl group, or a 1,3-dioxolanyl group. Or a 1,3-dioxanyl group, and more preferably a 1,3-dioxolanyl group or a 1,3-dioxanyl group.

  N in the formula (1) is an integer of 0 to 5. However, when n is 2 or more, two or more R2s represent independent substituents, and may be the same or different, and can be arbitrarily selected.

  R3 in the formula (1) is a hydrogen atom, a nitro group, a halogen atom, a C1 to C6 alkyl group optionally substituted with a substituent C, a C1 to C6 haloalkyl group, or a C1 to C6 optionally substituted with a substituent C. Good C3-C8 cycloalkyl group, C2-C6 alkenyl group optionally substituted with substituent C, C2-C6 haloalkenyl group, C2-C6 alkynyl group optionally substituted with substituent C , A C2-C6 haloalkynyl group, a C1-C6 alkoxy group optionally substituted with a substituent C, a C1-C6 haloalkoxy group, R30-L3- (where R30 has the same meaning as R23 described above). And L3 has the same meaning as L2 above), R31R32N- (where R31 and R32 have the same meanings as R21 and R22), or R33C (= O)-(this In, R33 represents a.) Represents an alkyl group, a haloalkyl group of C1 -C6 or a cycloalkyl group of C3 -C8, a C1 -C6.

Among them, R3 is a hydrogen atom, a halogen atom, a C1 to C6 alkyl group optionally substituted with a substituent C, a C3 to C8 cycloalkyl group optionally substituted with a substituent C, or a substituent C as appropriate. An optionally substituted C2-C6 alkynyl group, a C1-C6 alkoxy group optionally substituted with a substituent C, or R30-L3- (where R30 and L3 are as defined above). Is preferred,
In particular, a hydrogen atom, a halogen atom, or a C1-C6 alkyl group optionally substituted with a substituent C is preferable,
Further, a hydrogen atom, a halogen atom, or a C1-C6 alkyl group is preferable.

The “substituent C” in the formula (1) includes 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, R31R32N -(Where R31 and R32 have the same meanings as R21 and R22 above) and R30-L3- (where R30 has the same meaning as R23 above, and L3 has the same meaning as above L2. At least one selected from the group consisting of: Among them, the substituent C is preferably a cyano group, a C1 to C6 alkoxy group, or R30-L3- (where R30 and L3 have the same meanings as described above).
Particularly, a cyano group or a C1 to C6 alkoxy group is preferable.

Preferred specific examples of the substituent C include a hydroxyl group; a cyano group;
As a C3-C8 cycloalkyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group;
A C1-C6 alkoxy group such as a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group, and an isobutoxy group;
As C1 to C6 haloalkoxy groups, difluoromethoxy, trifluoromethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 3,3-difluoropropyloxy, and 3,3 , 3-trifluoropropyloxy group;
A C3-C8 cycloalkoxy group such as a cyclopropyloxy group, a cyclobutoxy group, a cyclopentyloxy group, and a cyclohexyloxy group;
R31R32N- (wherein R31 and R32 have the same meanings as R21 and R22 above), as an amino group, a dimethylamino group, an ethylmethylamino group, a diethylamino group, a pyrrolidinyl group, and a piperidinyl group;
And R30-L3- (where R30 has the same meaning as R23 described above, and L3 has the same meaning as L2 above) as a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, A trifluoromethanesulfinyl group, and a trifluoromethanesulfonyl group.

More preferred specific examples of the substituent C include a hydroxyl group; a cyano group;
A C3-C8 cycloalkyl group such as a cyclopropyl group and a cyclobutyl group;
A methoxy group and an ethoxy group as the C1-C6 alkoxy group;
A C1-C6 haloalkoxy group such as a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, and a 2,2,2-trifluoroethoxy group;
A C3-C8 cycloalkoxy group such as a cyclopropyloxy group and a cyclobutoxy group;
R31R32N- (where R31 and R32 have the same meanings as described above), such as a dimethylamino group, an ethylmethylamino group, and a diethylamino group;
And R30-L3- (where R30 and L3 are as defined above), include a methylthio group, a methanesulfinyl group, and a methanesulfonyl group.

  R3 in the formula (1) includes a hydrogen atom and a nitro group.

  The “halogen atom” for R 3 in the formula (1) is as defined above, and is preferably a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, and more preferably a chlorine atom or a bromine atom. .

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

  The “C1 to C6 haloalkyl group” for R3 in the formula (1) is as defined above, and is preferably a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, a 2,2,2 group. -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 meaning as defined above, and is preferably a cyclopropyl group. , A cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, and more preferably a cyclopropyl group or a cyclobutyl group. When it has the substituent C, the hydrogen atom in the C3-C8 cycloalkyl group is arbitrarily substituted by the substituent C.

  The C2-C6 alkenyl group of the "C2-C6 alkenyl group optionally substituted with substituent C" for R3 in formula (1) is as defined above, and is preferably a vinyl group, 1- It is a propenyl group, an allyl group, a 1-butenyl group, a 2-butenyl group or a 3-butenyl group, more preferably a vinyl group, a 1-propenyl group or an allyl group. When it has the substituent C, the hydrogen atom in the C2-C6 alkenyl group is optionally substituted by the substituent C.

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

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

  The “C2 to C6 haloalkynyl group” for R3 in the formula (1) is as defined above, and preferably is a 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, and more preferably a 3,3-difluoro-1-propynyl group or a 3,3,3-trifluoro-1-propynyl group.

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

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

  In "R30-L3-" in R3 of Formula (1), R30 has the same meaning as R23, and L3 has the same meaning as L2. "R30-L3-" 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, a methanesulfinyl group Or a methanesulfonyl group.

  In "R31R32N-" in R3 of the formula (1), R31 and R32 have the same meanings as R21 and R22 described above, and preferably, an amino group, a dimethylamino group, an ethylmethylamino group, a diethylamino group, a pyrrolidinyl group, or It is a piperidinyl group, more preferably a dimethylamino group, an ethylmethylamino group, or a diethylamino group.

  Each of "R33C (= O)-" in R3 of the formula (1) (here, R33 represents a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, or a C3 to C8 cycloalkyl group). The terms are as defined above. "R33C (= O)-" is preferably an acetyl group, a propionyl group, a difluoroacetyl group, a trifluoroacetyl group, or a cyclopropanecarbonyl group, and more preferably an acetyl group, a difluoroacetyl group, or a trifluoro group. Acetyl group.

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

  Y in the formula (1) represents a phenyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, a thienyl group, a thiazolyl group, or an isothiazolyl group, and among them, a phenyl group or a pyridyl group is preferable. A phenyl group is preferred.

  In the phenyl group, the substituent D is substituted at the ortho position, the substituent D1 is independently substituted with 0 to 3 as appropriate, and the substituent D2 is further substituted independently with 1 to 4 as appropriate.

  In the pyridyl group, the pyridazinyl group, the pyrimidinyl group, the pyrazinyl group, or the triazinyl group, the substituent D is substituted at the ortho position, and the substituents D1 are each independently optionally substituted with 0 to 2, and further substituted. The group D2 is independently and appropriately substituted with 1 to 2 groups.

  In the thienyl group, the thiazolyl group, or the isothiazolyl group, the substituent D is substituted at the ortho position, the substituents D1 are each independently optionally substituted with 0 to 1, and the substituents D2 are each independently substituted. Substitute 1-2 as appropriate.

  The “substituent D” in the formula (1) is selected from the group consisting of a halogen atom, a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, a C1 to C6 alkoxy group, and a C1 to C6 haloalkoxy group. Represents at least one type.

Among them, the substituent D is preferably a halogen atom or a C1 to C6 alkyl group,
Particularly, a halogen atom is preferable.

As a preferable specific example of the substituent D,
As a halogen atom, a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom;
Methyl, ethyl and propyl groups as C1-C6 alkyl groups;
As C1 to C6 haloalkyl groups, difluoromethyl group, trifluoromethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, 3,3-difluoropropyl group, and 3,3,3 A trifluoropropyl group;
A C1-C6 alkoxy group such as a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group, an isobutoxy group, and a t-butoxy group;
And a C1-C6 haloalkoxy group such as difluoromethoxy, trifluoromethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 3,3-difluoropropyloxy, and 3, A 3,3-trifluoropropyloxy group is exemplified.

As more preferred specific examples of the substituent D,
As a halogen atom, a fluorine atom, a chlorine atom, and a bromine atom;
A methyl group and an ethyl group as the C1 to C6 alkyl group;
C1-C6 haloalkyl groups such as difluoromethyl group, trifluoromethyl group, 2,2-difluoroethyl group and 2,2,2-trifluoroethyl group; C1-C6 alkoxy groups such as methoxy group and ethoxy group Propyloxy and isopropyloxy groups;
In addition, examples of the C1 to C6 haloalkoxy group include a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, and a 2,2,2-trifluoroethoxy group.

  The “substituent D1” in the formula (1) includes a hydroxyl group, a halogen atom, a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group, a C1 to C6 alkoxy group, a C1 to C6. And at least one selected from the group consisting of C3 to C8 cycloalkoxy groups.

Among them, the substituent D1 is preferably a hydroxyl group, a halogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group,
Particularly, a halogen atom, a C1 to C6 alkyl group, or a C1 to C6 alkoxy group is preferable.

Preferred specific examples of the substituent D1 include a hydroxyl group;
As a halogen atom, a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom;
Methyl, ethyl and propyl groups as C1-C6 alkyl groups;
As a C1-C6 haloalkyl group, a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, and a 2,2,2-trifluoroethyl group;
As a C3-C8 cycloalkyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group;
A C1-C6 alkoxy group such as a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group, an isobutoxy group, and a t-butoxy group;
As C1 to C6 haloalkoxy groups, difluoromethoxy, trifluoromethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 3,3-difluoropropyloxy, and 3,3 , 3-trifluoropropyloxy group;
And C3-C8 cycloalkoxy groups include cyclopropyloxy, cyclobutoxy, cyclopentyloxy, and cyclohexyloxy groups.

More preferred specific examples of the substituent D1 include a hydroxyl group;
As a halogen atom, a fluorine atom, a chlorine atom, and a bromine atom;
A methyl group and an ethyl group as the C1 to C6 alkyl group;
As a C1-C6 haloalkyl group, a difluoromethyl group and a trifluoromethyl group;
A C3-C8 cycloalkyl group such as a cyclopropyl group and a cyclobutyl group;
A C1-C6 alkoxy group such as a methoxy group, an ethoxy group, a propyloxy group, and an isopropyloxy group;
A C1-C6 haloalkoxy group such as a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, and a 2,2,2-trifluoroethoxy group;
And as the C3-C8 cycloalkoxy group, a cyclopropyloxy group and a cyclobutoxy group can be mentioned.

The “substituent D2” in the formula (1) is a C2 to C6 alkenyl group, a C2 to C6 haloalkenyl group which may be appropriately substituted with a cyano group, a nitro group, or a substituent B, and is optionally substituted with a substituent B. A C2-C6 alkynyl group, a C2-C6 haloalkynyl group, a C2-C6 alkenyloxy group optionally substituted with a substituent B, a C2-C6 haloalkenyloxy group,
A C3-C6 alkynyloxy group, a C3-C6 haloalkynyloxy group, a C2-C6 alkoxyalkoxy group, a C2-C6 cyanoalkoxy group, a C4-C9 cycloalkylalkoxy optionally substituted with a substituent B Group, an aryl group optionally substituted with a substituent D, a heteroaryl group optionally substituted with a substituent D, an aryloxy group optionally substituted with a substituent D, optionally substituted with a substituent D A heteroaryloxy group, an aralkyloxy group optionally substituted with a substituent D, R40 (CH2) pU- (where p represents an integer of 1 to 3, and R40 represents 1 to 2 A 3- to 6-membered ring group containing two oxygen atoms, R41R42N- (where R41 and R42 have the same meanings as R21 and R22 described above), or R43-L4- Here, R43 has the same meaning as R14, L4 has the same meaning as L1, and U represents an oxygen atom or a sulfur atom.), R41R42N- (here, R41 And R42 have the same meaning as described above.), R43-L4- (where R43 has the same meaning as R14, and L4 has the same meaning as L1), R44C (= O)-( Here, R44 represents a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group, a C1 to C6 alkoxy group, a C1 to C6 halo An alkoxy group, a C3-C8 cycloalkoxy group, or R41R42N- (where R41 and R42 have the same meanings as described above); R44C (= O) O- (where R44 is as defined above) Synonymous ), R45C (= O) N (R46)-(where R45 is a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C6 Represents a C8 cycloalkyl group, a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group, or R41R42N- (where R41 and R42 are as defined above). , R46 represents a hydrogen atom, a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, or a C3 to C8 cycloalkyl group optionally substituted with a substituent A), R47R48C = NO- (Where R47 and R48 are each independently a hydrogen atom, a C1 to C6 alkyl group optionally substituted with a substituent A, a C1 to C6 haloalkyl A C3 to C8 cycloalkyl group, a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group, or R41R42N- (where R41 and R42 are as defined above. . ). ), 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 D2 is appropriately substituted with a cyano group, a C2 to C6 alkenyl group optionally substituted with a substituent B, a C2 to C6 alkynyl group optionally substituted with a substituent B, and a substituent B. C2-C6 alkenyloxy group, C3-C6 alkynyloxy group optionally substituted with substituent B, C2-C6 alkoxyalkoxy group, C2-C6 cyanoalkoxy group, C4-C9 cycloalkyl An alkoxy group, a heteroaryl group optionally substituted with a substituent D, an aryloxy group optionally substituted with a substituent D, an aralkyloxy group optionally substituted with a substituent D, R40 (CH2) p -U- (where p, R40 and U are as defined above),
R41R42N- (where R41 and R42 are as defined above), R43-L4- (where R43 and L4 are as defined above), R44C (= O) O- (where R44 is as defined above, or R47R48C = N-O- (where R47 and R48 are as defined above),
In particular, a cyano group, a C2-C6 alkynyl group optionally substituted with a substituent B, a C2-C6 alkenyloxy group optionally substituted with a substituent B, or a substituent B optionally. A C3-C6 alkynyloxy group, a C2-C6 alkoxyalkoxy group, a C2-C6 cyanoalkoxy group, a C4-C9 cycloalkylalkoxy group, a heteroaryl group optionally substituted with a substituent D, a substituent D And an aralkyloxy group optionally substituted with a substituent D, R40 (CH2) pU- (where p, R40 and U are as defined above). ,
R41R42N- (where R41 and R42 are as defined above), R43-L4- (where R43 and L4 are as defined above), R44C (= O) O- (where R44 is as defined above, or R47R48C = NO- (here, R47 and R48 are as defined above).

  The substituent D2 in the formula (1) includes a cyano group and a nitro group.

  The C2 to C6 alkenyl group of the "C2 to C6 alkenyl group optionally substituted with the substituent B" in the substituent D2 of the formula (1) has the same meaning as defined above, and is preferably a vinyl group, A 1-propenyl group, an allyl group, a 1-butenyl group, a 2-butenyl group, or a 3-butenyl group is more preferable, and a vinyl group, a 1-propenyl group, or an allyl group is more preferable. When the compound has the substituent B, the hydrogen atom in the C2 to C6 alkenyl group is optionally substituted with the substituent B.

  The “C2 to C6 haloalkenyl group” in the substituent D2 in the formula (1) is as defined above, and is preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, or a 2,2-dichloro group. It is a vinyl group, a 3-fluoroallyl group, a 3,3-difluoroallyl group, or a 3,3-dichloroallyl group, and more preferably a 2-fluorovinyl group or a 2,2-difluorovinyl group.

  The C2 to C6 alkynyl group of the “C2 to C6 alkynyl group optionally substituted with the substituent B” in the substituent D2 of the formula (1) has the same meaning as the above definition, and is preferably an ethynyl group, A 1-propynyl group, a propargyl group, a 1-butynyl group, a 2-butynyl group, or a 3-butynyl group, more preferably an ethynyl group, a 1-propynyl group, or a propargyl group, and particularly preferably an ethynyl group; It is. When it has the substituent B, the hydrogen atom in the C2 to C6 alkynyl group is optionally substituted by the substituent B.

  The “C2 to C6 haloalkynyl group” in the substituent D2 in the formula (1) is as defined above, and is preferably a 3,3-difluoro-1-propynyl group or a 3,3,3-trifluoro group. -1-propynyl, 4,4-difluoro-1-butynyl, 4,4-difluoro-2-butynyl, 4,4,4-trifluoro-1-butynyl, or 4,4,4-triphenyl It is a fluoro-2-butynyl group, more preferably a 3,3-difluoro-1-propynyl group or a 3,3,3-trifluoro-1-propynyl group.

  The C2 to C6 alkenyloxy group of the "C2 to C6 alkenyloxy group optionally substituted with the substituent B" in the substituent D2 of the formula (1) has the same meaning as described above, and is preferably 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, and particularly preferably Is an allyloxy group. When it has the substituent B, the hydrogen atom in the C2-C6 alkenyloxy group is optionally substituted by the substituent B.

  The “C2 to C6 haloalkenyloxy group” in the substituent D2 in the formula (1) is as defined above, and is preferably a 2-fluorovinyloxy group, a 2,2-difluorovinyloxy group, A 2-dichlorovinyloxy group, a 3-fluoroallyloxy group, a 3,3-difluoroallyloxy group, or a 3,3-dichloroallyloxy group, more preferably a 2-fluorovinyloxy group, or a 2,2 -A difluorovinyloxy group.

  The C3-C6 alkynyloxy group of the "C3-C6 alkynyloxy group optionally substituted with the substituent B" in the substituent D2 of the formula (1) is as defined above, and is preferably propargyl. It is an oxy group, a 2-butynyloxy group or a 3-butynyloxy group, and more preferably a propargyloxy group. When it has the substituent B, the hydrogen atom in the C3-C6 alkynyloxy group is optionally substituted by the substituent B.

  The “C3-C6 haloalkynyloxy group” in the substituent D2 of the formula (1) has the same meaning as the above definition, and is preferably a 4,4-difluoro-2-butynyloxy group, a 4-chloro-4,4 -Difluoro-2-butynyloxy group, 4-bromo-4,4-difluoro-2-butynyloxy group or 4,4,4-trifluoro-2-butynyloxy group, and more preferably 4,4-difluoro- It is a 2-butynyloxy group or a 4,4,4-trifluoro-2-butynyloxy group.

  The “C2 to C6 alkoxyalkoxy group” in the substituent D2 in the formula (1) is as defined above, and is preferably a methoxymethoxy group, an ethoxymethoxy group, a propyloxymethoxy group, an isopropyloxymethoxy group, or a methoxy group. An ethoxy group, an ethoxyethoxy group, a propyloxyethoxy group, or a methoxypropyloxy group, more preferably a methoxymethoxy group, an ethoxymethoxy group, a methoxyethoxy group, an ethoxyethoxy group, or a methoxypropyloxy group, particularly preferably Is a methoxymethoxy group, a methoxyethoxy group, or a methoxypropyloxy group.

  The “C2 to C6 cyanoalkoxy group” in the substituent D2 of the formula (1) is as defined above, and is preferably an acetonitrileoxy group, a 3-propanenitryloxy group, a 4-butanenitryloxy group, -Propanenitrileoxy group or 2-methylpropanenitrile-3-oxy group, more preferably acetonitrileoxy group or 3-propanenitrileoxy group, particularly preferably acetonitrileoxy group.

  The “C4-C9 cycloalkylalkoxy group” in the substituent D2 of the formula (1) has the same meaning as the above definition, and is preferably a cyclopropylmethoxy group, a cyclobutylmethoxy group, a cyclopentylmethoxy group, a cyclohexylmethoxy group, A cyclopropylethoxy group, a cyclobutylethoxy group, a cyclopentylethoxy group, a cyclohexylethoxy group, or a cyclopropylpropanyloxy group, more preferably a cyclopropylmethoxy group, a cyclopentylmethoxy group, or a cyclopropylethoxy group, Preferably, it is a cyclopropylmethoxy group.

  The aryl group of the “aryl group optionally substituted with the substituent D” in the substituent D2 of the formula (1) has the same meaning as the above definition, and is preferably a phenyl group. When it has the substituent D, the hydrogen in the aryl group is optionally substituted by the substituent D.

  The heteroaryl group of the “heteroaryl group optionally substituted with the substituent D” in the substituent D2 of the formula (1) is as defined above, and is preferably a pyridyl group, a pyrazinyl group, a thienyl group, Thiazolyl group, isothiazolyl group, furyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, triazolyl group, oxadiazolyl group, or tetrazolyl group, more preferably pyridyl group, imidazolyl group, pyrazolyl group, triazolyl group, tetrazolyl group And particularly preferably a 1H-pyrazol-1-yl group or a 1H-1,2,4-triazol-1-yl group. When the compound has the substituent D, hydrogen in the heteroaryl group is optionally substituted by the substituent D.

  The aryloxy group of the “aryloxy group optionally substituted with the substituent D” in the substituent D2 of the formula (1) is as defined above, and is preferably a phenoxy group or a naphthyloxy group. And more preferably a phenoxy group. When it has the substituent D, the hydrogen atom in the aryloxy group is optionally substituted by the substituent D. The aryloxy group having the substituent D is preferably a 4-methoxyphenoxy group.

  The heteroaryloxy group of the “heteroaryloxy group optionally substituted with the substituent D” in the substituent D2 of the formula (1) is as defined above, and is preferably a pyridyloxy group or a pyridazinyl group. Roxy group, pyrimidinyloxy group, pyrazinyloxy group, pyrazolyloxy group, triazinyloxy group, tetrazinyloxy group, thienyloxy group, thiazolyloxy group, isothiazolyloxy group, or thiadiazolyloxy group, more preferably Is a pyridyloxy group, a pyridazinyloxy group, a pyrimidinyloxy group, a pyrazinyloxy group, or a pyrazolyloxy group. When the compound has the substituent D, a hydrogen atom in the heteroaryloxy group is optionally substituted by the substituent D.

  The aralkyloxy group of the “aralkyloxy group optionally substituted with the substituent D” in the substituent D2 of the formula (1) is as defined above, and is preferably a benzyloxy group, a phenethyloxy group, or It is a phenylpropyloxy group, more preferably a benzyloxy group or a phenethyloxy group, particularly preferably a benzyloxy group. When it has the substituent D, the hydrogen atom in the aralkyloxy group is optionally substituted by the substituent D.

  "R40 (CH2) pU-" in the substituent D2 of the formula (1) (where p represents an integer of 1 to 3, and R40 is a 3- to 6-membered ring containing 1-2 oxygen atoms) R41R42N- (where R41 and R42 have the same meanings as R21 and R22 above), or R43-L4- (where R43 has the same meaning as R14 above, and L4 has the same meaning as the above. And U represents an oxygen atom or a sulfur atom.) Has the same meaning as defined above. R40 is preferably an oxolanyl group, an oxanyl group, a 1,3-dioxolanyl group, a 1,3-dioxanyl group, a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, a trifluoromethanesulfinyl group, a trifluoromethanesulfonyl group Group, amino group, methylamino group, ethylamino group, (methoxymethyl) amino group, (2-methoxyethyl) amino group, (cyanomethyl) amino group, (2-cyanoethyl) amino group, dimethylamino group, ethylmethylamino Group, diethylamino group, (methoxymethyl) methylamino group, (2-methoxyethyl) methylamino group, (cyanomethyl) methylamino group, (2-cyanoethyl) methylamino group, 2,2-difluoroethylamino group, 2,2-Trifluo An ethylamino group, a cyclopropylamino group, a (cyclopropyl) methylamino group, a pyrrolidinyl group, or a piperidinyl group, more preferably an oxolanyl group, an oxanyl group, a 1,3-dioxolanyl group, a 1,3-dioxanyl group, A methylthio group, a methanesulfinyl group, a methanesulfonyl group, a dimethylamino group, an ethylmethylamino group, or a diethylamino group, and p is preferably an integer of 1 to 3, more preferably an integer of 2 to 3. And U is preferably an oxygen atom. R40 (CH2) pU- is preferably a (tetrahydrofuran-2-yl) methoxy group, a (1,3-dioxolan-2-yl) methoxy group, a (dimethylamino) ethoxy group, or a (dimethylamino) propyloxy group. A (methylthio) methoxy group, a (methylthio) ethoxy group or a (methylthio) propyl group, more preferably a (tetrahydrofuran-2-yl) methoxy group or a (1,3-dioxolan-2-yl) methoxy group , (Dimethylamino) ethoxy, (dimethylamino) propyloxy, or (methylthio) methoxy.

  R41 and R42 of "R41R42N-" in the substituent D2 in the formula (1) have the same meaning as described above. As "R41R42N-", preferably, an amino group, a methylamino group, an ethylamino group, a (methoxymethyl) amino group, a (2-methoxyethyl) amino group, a (cyanomethyl) amino group, a (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- A difluoroethylamino group, a 2,2,2-trifluoroethylamino group, a cyclopropylamino group, a (cyclopropyl) methylamino group, a pyrrolidinyl group, or a piperidinyl group, more preferably a methylamino group or an ethylamino group , Dimethylamino group, ethylmethylamino group, or A diethylamino group, particularly preferably a methylamino group or a dimethylamino group.

  R43 and L4 of "R43-L4-" in the substituent D2 of the formula (1) are as defined above. As "R43-L4-", 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, a methanesulfinyl group Or a methanesulfonyl group, particularly preferably a methylthio group.

  “R44C (＝ O) —” in the substituent D2 of the formula (1) (where R44 is a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, a C3 to Represents a C8 cycloalkyl group, a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group, or R41R42N- (where R41 and R42 have the same meanings as described above). Each term in ()) is synonymous with the above definition. As "R44C (= O)-", preferably, acetyl, methoxyacetyl, cyanoacetyl, propionyl, difluoroacetyl, trifluoroacetyl, cyclopropanecarbonyl, methoxycarbonyl, ethoxycarbonyl, 2 , 2-Difluoroethoxycarbonyl group, 2,2,2-trifluoroethoxycarbonyl group, 3,3,3-trifluoropropyloxycarbonyl group, cyclopropyloxycarbonyl group, aminocarbonyl group, methylaminocarbonyl group, ethylamino Carbonyl group, (methoxymethyl) aminocarbonyl group, (2-methoxyethyl) aminocarbonyl group, (cyanomethyl) aminocarbonyl group, (2-cyanoethyl) aminocarbonyl group, dimethylaminocarbonyl group, ethylmethyl Minocarbonyl group, diethylaminocarbonyl group, (methoxymethyl) methylaminocarbonyl group, (2-methoxyethyl) methylaminocarbonyl group, (cyanomethyl) methylaminocarbonyl group, (2-cyanoethyl) methylaminocarbonyl group, 2,2- A difluoroethylaminocarbonyl group, a 2,2,2-trifluoroethylaminocarbonyl group, a cyclopropylaminocarbonyl group, a (cyclopropyl) methylaminocarbonyl group, a pyrrolidinylcarbonyl group, or a piperidinylcarbonyl group; Preferably, acetyl group, methoxyacetyl group, cyanoacetyl group, difluoroacetyl group, trifluoroacetyl group, methoxycarbonyl group, ethoxycarbonyl group, aminocarbonyl group, dimethylaminocarbonyl , Ethyl-methylaminocarbonyl group or diethylamino group.

  R44 in “R44C (＝ O) O—” in the substituent D2 in the formula (1) has the same meaning as described above. As “R44C (＝ O) O—”, preferably, acetyloxy group, methoxyacetyloxy group, cyanoacetyloxy group, propionyloxy group, difluoroacetyloxy group, trifluoroacetyloxy group, cyclopropanecarbonyloxy group, methoxy Carbonyloxy group, ethoxycarbonyloxy group, 2,2-difluoroethoxycarbonyloxy group, 2,2,2-trifluoroethoxycarbonyloxy group, 3,3,3-trifluoropropyloxycarbonyloxy group, cyclopropyloxycarbonyl An oxy group, an aminocarbonyloxy group, a methylaminocarbonyloxy group, an ethylaminocarbonyloxy group, a (methoxymethyl) aminocarbonyloxy group, a (2-methoxyethyl) aminocarbonyloxy group, Methyl) aminocarbonyloxy group, (2-cyanoethyl) aminocarbonyloxy group, dimethylaminocarbonyloxy group, ethylmethylaminocarbonyloxy group, diethylaminocarbonyloxy group, (methoxymethyl) methylaminocarbonyloxy group, (2-methoxyethyl ) Methylaminocarbonyloxy group, (cyanomethyl) methylaminocarbonyloxy group, (2-cyanoethyl) methylaminocarbonyloxy group, 2,2-difluoroethylaminocarbonyloxy group, 2,2,2-trifluoroethylaminocarbonyloxy A cyclopropylaminocarbonyloxy group, a (cyclopropyl) methylaminocarbonyloxy group, a pyrrolidinylcarbonyloxy group, or a piperidinylcarbonyloxy group; Preferably, acetyloxy group, methoxyacetyloxy group, cyanoacetyloxy group, difluoroacetyloxy group, trifluoroacetyloxy group, methoxycarbonyloxy group, ethoxycarbonyloxy group, aminocarbonyloxy group, dimethylaminocarbonyloxy group, It is an ethylmethylaminocarbonyloxy group or a diethylaminocarbonyloxy group, particularly preferably an acetyloxy group.

  “R45C (＝ O) N (R46) —” in the substituent D2 of the formula (1) (where R45 is a hydrogen atom, a C1 to C6 alkyl group optionally substituted with a substituent A, A C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or R41R42N- (where R41 and R42 are as defined above) R46 represents a hydrogen atom, a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, or a C3 to C8 cycloalkyl group which may be appropriately substituted with the substituent A.) Are the same as defined above. As R45, preferably, a hydrogen atom, a methyl group, a methoxymethyl group, a cyanomethyl group, an ethyl group, a difluoromethyl group, a trifluoromethyl group, a cyclopropyl group, a methoxy group, an ethoxy group, a 2,2-difluoroethoxy, 2,2-trifluoroethoxy group, cyclopropyloxy group, amino group, methylamino group, ethylamino group, (methoxymethyl) amino group, (2-methoxyethyl) amino group, (cyanomethyl) amino group, (2- (Cyanoethyl) amino group, dimethylamino group, ethylmethylamino group, diethylamino group, (methoxymethyl) methylamino group, (2-methoxyethyl) methylamino group, (cyanomethyl) methylamino group, (2-cyanoethyl) methylamino group , 2,2-difluoroethylamino group, 2,2,2-to A fluoroethylamino group, a cyclopropylamino group, a (cyclopropyl) methylamino group, a pyrrolidinyl group, or a piperidinyl group, more preferably a hydrogen atom, a methyl group, a methoxymethyl group, a cyanomethyl group, a difluoromethyl group, a trifluoromethyl group; A methyl group, a methoxy group, an ethoxy group, an amino group, a dimethylamino group, an ethylmethylamino group, or a diethylamino group. Further, as R46, preferably a hydrogen atom, a methyl group, a methoxymethyl group, an ethoxymethyl group, a cyanomethyl group, an ethyl group, a 2-methoxyethyl group, a 2-ethoxyethyl group, a 2-cyanoethyl group, a propyl group, Examples include a 2-difluoroethyl group, a 2,2,2-trifluoroethyl group, and a cyclopropyl group, and more preferably, a hydrogen atom, a methyl group, a methoxymethyl group, a cyanomethyl group, an ethyl group, and a 2-methoxyethyl group. , 2,2-difluoroethyl group or 2,2,2-trifluoroethyl group.

  "R47R48C = NO-" in the substituent D2 of the formula (1) (where R47 and R48 are each independently a hydrogen atom or a C1 to C6 alkyl which may be appropriately substituted with the substituent A) A C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or R41R42N- (where R41 and R42 Has the same meaning as defined above.)) Are the same as defined above, and R47 and R48 are preferably methyl, ethyl, propyl, isopropyl, trifluoromethyl, 2 , 2,2-trifluoroethyl, cyclopropyl, cyclopentyl, cyclohexyl, methoxy, ethoxy, isopropyl Oxy, difluoromethoxy, trifluoromethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, amino, methylamino Group, ethylamino group, (methoxymethyl) amino group, (2-methoxyethyl) amino group, (cyanomethyl) amino group, (2-cyanoethyl) amino group, dimethylamino group, ethylmethylamino group, diethylamino group, (methoxy Methyl) methylamino group, (2-methoxyethyl) methylamino group, (cyanomethyl) methylamino group, (2-cyanoethyl) methylamino group, 2,2-difluoroethylamino group, 2,2,2-trifluoroethyl Amino group, cyclopropylamino group, (cyclopropyl) A tylamino group, a pyrrolidinyl group, or a piperidinyl group, more preferably a methyl group, an ethyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a methoxy group, an ethoxy group, a 2,2,2- It is a trifluoroethoxy group, a dimethylamino group, an ethylmethylamino group, or a diethylamino group. R47R48C = NO- is preferably a dimethyliminooxy group, an ethylmethyliminooxy group, or a diethyliminooxy group, and particularly preferably a dimethyliminooxy group.

  The “3- to 6-membered ring group containing 1 to 2 oxygen atoms” in the substituent D2 of the formula (1) has the same meaning as the above definition, and is preferably an oxolanyl group, an oxanyl group, a 1,3- It is a dioxolanyl group or a 1,3-dioxanyl group, and more preferably an oxolanyl group or a 1,3-dioxolanyl group.

  Hereinafter, specific examples of Y in the formula (1) will be described in detail.

で表される部分構造（ここで、Ｄ、Ｄ１およびＤ２は前記と同義であり、ｍａは０〜３の整数を表し、ｍｂは１〜４の整数を表す。）を表す。A) When Y is a phenyl group, Y is represented by the formula (a)

(Where D, D1 and D2 have the same meanings as above, ma represents an integer of 0 to 3, and mb represents an integer of 1 to 4).

  Ma in the formula (a) represents an integer of 0 to 3.

  When ma in the formula (a) is 2 or more, two or more D1s each represent an independent substituent, which may be the same or different, and can be arbitrarily selected.

  Mb in the formula (a) represents an integer of 1 to 4.

  When mb in the formula (a) is 2 or more, two or more D2s each represent an independent substituent, which may be the same or different, and can be arbitrarily selected.

  In the present specification, when Y is a phenyl group, the ortho position means the position of the phenyl group having the substituent D as shown in the formula (a).

  A phenyl group in which the substituent D is located in the ortho position is a feature of the present invention.

  Preferred specific examples of the formula (a) include a 2-D-4-D2-phenyl group, a 2-D-6-D2-phenyl group, a 2-D-4-D2-6-D1-phenyl group, and a 2-D -4-D2-5-D1-phenyl group, 2-D-3-D1-4-D2-phenyl group, 2-D-4-D1-6-D2-phenyl group, 2-D-3-D1- A 6-D2-phenyl group, a 2-D-5-D1-6-D2-phenyl group, or a 2-D-4-D2-6-D2-phenyl group; a more preferred specific example is 2-D-phenyl; A 4-D2-phenyl group, a 2-D-6-D2-phenyl group, a 2-D-4-D2-6-D1-phenyl group, or a 2-D-4-D1-6-D2-phenyl group And a 2-D-4-D1-6-D2-phenyl group is particularly preferred. Here, for example, "2-D-6-D2-phenyl group" means a disubstituted phenyl group having a substituent D at the 2-position and a substituent D2 at the 6-position, and the same applies to the following description.

で表される部分構造（ここで、Ｄ、Ｄ１、Ｄ２は前記と同義であり、ｍｃは０〜２の整数を表し、ｍｄは１〜３の整数を表す。）を表す。B) When Y is a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, or a triazinyl group, Y is represented by the formula (b)

(Where D, D1, and D2 have the same meanings as described above, mc represents an integer of 0 to 2, and md represents an integer of 1 to 3).

  G1, G2, G3 and G4 in the formula (b) are each independently and represent a carbon atom or a nitrogen atom. However, at least one of G1, G2, G3 and G4 is a nitrogen atom. Desirable G1, G2, G3 and G4 are those in which any one of G1, G2, G3 and G4 is a nitrogen atom. That is, it is a pyridyl group.

  Mc in the formula (b) represents an integer of 0 to 2.

  When mc in the formula (b) is 2 or more, two or more D1s each represent an independent substituent, and may be the same or different and can be arbitrarily selected.

  Md in the formula (b) represents an integer of 1 to 3.

  When md in the formula (b) is 2 or more, two or more D2s each represent an independent substituent, which may be the same or different, and can be arbitrarily selected.

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

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

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

  Preferred specific examples of the formula (b) include a 3-D-5-D2-2-pyridyl group, a 2-D-6-D2-3-pyridyl group, a 4-D-6-D2-3-pyridyl group, -D2-4-D-3-pyridyl group, 2-D-4-D2-3-pyridyl group, 2-D-4-D1-6-D2-3-pyridyl group, 2-D-4-D2- 6-D1-3-pyridyl group, 2-D1-4-D-6-D2-3-pyridyl group, 2-D2-4-D-6-D1-3-pyridyl group, or 3-D-5- D2-4-pyridyl group. More preferred specific examples include a 3-D-5-D2-2-pyridyl group, a 2-D-6-D2-3-pyridyl group, a 4-D-6-D2-3-pyridyl group, and a 2-D-4. —D1-6-D2-3-pyridyl, 2-D1-4-D-6-D2-3-pyridyl, or 3-D-5-D2-4-pyridyl.

式（ｃ−２）

または、式（ｃ−３）

で表される部分構造（ここで、Ｄ、Ｄ１、およびＤ２は前記と同義であり、ｍｅは０〜１の整数を表し、ｍｆは１〜２の整数を表す。）を表す。C) When Y is a thienyl group, a thiazolyl group, or an isothiazolyl group, Y is represented by the formula (c-1)

Formula (c-2)

Or the formula (c-3)

(Where D, D1, and D2 have the same meanings as described above, me represents an integer of 0 to 1, and mf represents an integer of 1 to 2).

  G5 and G6 in the formulas (c-1), (c-2) and (c-3) are each independently and represent a carbon atom or a nitrogen atom.

  In the formulas (c-1), (c-2), and (c-3), me represents an integer of 0 to 1.

  Mf in the formulas (c-1), (c-2) and (c-3) represents an integer of 1 or 2.

  When mf in the formulas (c-1), (c-2) and (c-3) is 2, D2 of 2 represents an independent substituent, which may be the same or different, and may be arbitrarily selected. can do.

  In the present specification, when Y is a thienyl group, a thiazolyl group, or an isothiazolyl group, the ortho position is a substituted group as shown in the formulas (c-1), (c-2) and (c-3). The group D means the position of the 5-membered ring in which it is located.

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

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

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

  A thienyl, thiazolyl, or isothiazolyl group in which the substituent D is located in the ortho position is a feature of the present invention.

で表される部分構造（式中、Ｄ、Ｄ１、およびＤ２は前記と同義である。）であり、
さらに好ましい具体例は、式（ａ−１）で表される部分構造である。In Y of the formula (1), a preferable specific example is that Y is the formula (a-1) or the formula (b-1)

(Wherein D, D1, and D2 have the same meanings as described above);
A more preferred specific example is a partial structure represented by the formula (a-1).

で表される箇所を表す。The bond including the broken line part in the equation (1) is

Represents a portion represented by.

  The bond containing the broken line in Formula (1) represents a double bond or a single bond.

（式中、Ｒ１、Ｒ２、Ｒ３、Ｘ、Ｙおよびｎは、式（１）と同義である。）で表される化合物、またはその塩を表す。When the bond containing the dashed line in the formula (1) is a double bond, the formula (1a)

(Wherein, R1, R2, R3, X, Y and n have the same meanings as in formula (1)) or a salt thereof.

（式中、Ｒ１、Ｒ２、Ｒ３、Ｘ、Ｙおよびｎは、式（１）と同義である。）で表される化合物、またはその塩を表す。In the case where the bond including the broken line in the formula (1) is a single bond, the formula (1b)

(Wherein, R1, R2, R3, X, Y and n have the same meanings as in formula (1)) or a salt thereof.

  When R3 in the formula (1b) is a substituent other than hydrogen, it is either the R-form or the S-form alone, or a mixture of the R-form and the S-form in an arbitrary ratio.

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

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

  The compound represented by the formula (1) may include a geometric isomer. The isomer ratio at this time is a single ratio or a mixing ratio of an arbitrary ratio, and is not particularly limited.

  The compound represented by the formula (1) may form a salt in some cases. Acid salts such as hydrochloric acid, sulfuric acid, acetic acid, fumaric acid, and maleic acid, and metal salts such as sodium, potassium, and calcium are exemplified, but are not particularly limited as long as they can be used as agricultural and horticultural fungicides. There is no.

  In the bond including the above-described R1, substituent A, R2, substituent B, substituent B1, n, R3, substituent C, X, Y, substituent D, substituent D1, substituent D2, and a broken line portion. The range of all the compounds obtained by arbitrarily combining the preferable ranges is also described as the range of the compound represented by the formula (1) of the present invention or the intermediate compound thereof.

  Next, specific compounds of the present invention are represented by the structural formulas P-1 to P-414 shown in Table 1 (where X in Table 1 is an oxygen atom or a sulfur atom, and a bond containing a broken line is And a double bond or a single bond) and (R2) n shown in Table 2 (where R2 and n have the same meanings as described above). These compounds are for illustration only and the invention is not limited thereto.

  Hereinafter, for example, the description of "2-F-" in Table 2 means that a fluorine atom is bonded to the 2-position of the phenyl group to which (R2) n is bonded, and "2-F-3". The description "-HO-" means that a fluorine atom is bonded to the 2-position and a hydroxyl group is bonded to the 3-position, and the description "2,3-di-F" is a Means that a fluorine atom is bonded to the position, and the same applies to other descriptions.

  Hereinafter, a method for producing the compound represented by the formula (1) will be exemplified.

[Production method A]

  In the formula, R4 is a hydrogen atom, a hydroxyl group, a cyano group, a C1 to C6 alkyl group optionally substituted with a substituent A, a C1 to C6 haloalkyl group, or a C3 to C3 optionally substituted with a substituent A. C8 cycloalkyl group, C2-C6 alkenyl group optionally substituted with substituent A, C2-C6 haloalkenyl group, C2-C6 alkynyl group optionally substituted with substituent A, C2- C6 haloalkynyl group, C1-C6 alkoxy group optionally substituted with substituent A, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group optionally substituted with substituent A, substitution A C2-C6 alkenyloxy group optionally substituted with group A, a C2-C6 haloalkenyloxy group, a C3-C6 alkynyloxy group optionally substituted with substituent A, C To C6 haloalkynyloxy group or R10R11N- (wherein R10 and R11 are each independently a hydrogen atom or an alkyl group of C1 to C6), and R5 is a hydrogen atom or Represents a C1 to C6 alkyl group, and n, R2, R3, X and Y are as defined above.

Production method A is a method for obtaining a compound represented by the formula containing a preparation intermediate of the compound of the present invention and the present invention compound (1b-a), a compound R4NH ₂ represented by the formula (3) A reaction in the presence of an acid.

R4NH ₂ used in this reaction can be produced by obtaining or known manner as a commercially available product. R4NH ₂ are hydrochloric, may be those forming a salt with an acidic compound such as acetic acid, it is not particularly limited as long as the reaction proceeds to the desired.

R4NH ₂ used in this reaction may if 1 equivalent or more relative to the compound represented by formula (3), but are not particularly limited as long as the reaction proceeds to the desired, preferably, 1 It is equal to or more than 200 equivalents.

Examples of the acid used in this reaction include inorganic acids such as hydrochloric acid and sulfuric acid, and organic acids such as acetic acid, methanesulfonic acid and p-toluenesulfonic acid, and are not particularly limited as long as the desired reaction proceeds. But not preferably acetic acid. Further, when using salts with R4NH ₂ and the acidic compound, the use of acid is not essential.

The amount of the acid used in this reaction may if 1 equivalent or more relative to the R4NH _2, is not limited in particular as long as the reaction proceeds to the desired, preferably, one or more equivalents 200 equivalent or less is there. When the acid to be used is a liquid, it can be used as a solvent.

  Although a solvent can be used for this reaction, it is not always necessary.

  The solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but acidic solvents such as acetic acid and methanesulfonic acid, diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxy 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; ethyl acetate, isopropyl acetate and butyl acetate; Ester solvents, nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, and urea solvents such as 1,3-dimethyl-2-imidazolidinone solvent Dichloromethane, dichloroethane, chloroform, and halogen solvents such as carbon tetrachloride. These solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio. The solvent is preferably an acidic solvent, and 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 by weight based on the compound represented by the formula (3). is there.

  The temperature at which this reaction is performed is not particularly limited as long as the desired reaction proceeds, but is usually 50 ° 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 an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, or the like is dissolved, or a saline solution Etc. can be used arbitrarily. During the liquid separation operation, if necessary, a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene, an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate, diethyl ether, diisopropyl ether, or methyl- Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane. It is possible to add. In addition, these solvents can be used alone or as a mixture of two or more kinds at an arbitrary 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 (1ba) obtained above can be removed with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.

  The reaction mixture containing the compound represented by the formula (1ba) obtained above can be distilled under reduced pressure as long as the compound is not decomposed.

  The reaction mixture containing the compound represented by the formula (1ba) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the objective purity.

  According to the production method A, the compound represented by the formula (2) that can be produced when R4 represents a hydrogen atom in the compound represented by the formula (1ba) is a compound of the formula (1 It can be a useful production intermediate for obtaining the compound represented by 1b).

  Specific examples of the production intermediate represented by the formula (2) include structural formulas (I-1 to I-132) shown in Table 3, (R2) n shown in Table 2, and X (where X is An oxygen atom or a sulfur atom). These compounds are for illustration only and the invention is not limited thereto.

  A method for obtaining the formula (1b) of the present invention using the compound represented by the formula (2) as a production intermediate will be described.

[Production method B]

  In the formula, Lv represents a leaving group such as a methanesulfonyl group, a trifluoromethanesulfonyl group, a p-toluenesulfonyl group, a halogen atom and the like, and R1, R2, R3, X, Y and n are as defined above.

  The production method B is a method for obtaining a compound represented by the formula (1b), in which a production intermediate represented by the formula (2) is reacted with R1-Lv in a solvent in the presence of a base. The manufacturing method includes:

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

  The amount of R1-Lv used in this reaction may be at least 1 equivalent to the compound represented by the formula (2), and is not particularly limited as long as the desired reaction proceeds, but is preferably Is 1 equivalent or more and 10 equivalents or less.

  Examples of the base used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, and sodium hydride, but are not particularly limited as long as the desired reaction proceeds. It will not be done.

  The amount of the base used in this reaction may be one equivalent or more based on the compound represented by the formula (2), and is not particularly limited as long as the desired reaction proceeds. It is 1 equivalent or more and 10 equivalents or less.

  The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, and 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; and nitrile solvents such as acetonitrile; Amide solvents such as N-methylpyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, dichloromethane, dichloroethane, chloroform Holm, halogenated solvents such as carbon tetrachloride, dimethyl sulfoxide, sulfur-based solvents such as sulfolane, acetone, methyl ethyl ketone, ketone solvents such as methyl isobutyl ketone. These solvents can be used alone or as a mixture of two or more kinds at an arbitrary 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 by weight based on the compound represented by the formula (2). is there.

  The temperature at which this reaction is performed 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 an appropriate aqueous solution to the reaction mixture. When an aqueous solution is used, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, or the like is dissolved, thiosulfate An aqueous solution or salt solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved can be used arbitrarily. During the liquid separation operation, if necessary, a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene, an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate, diethyl ether, diisopropyl ether, or methyl- Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane. It is possible to add. In addition, these solvents can be used alone or as a mixture of two or more kinds at an arbitrary 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 (1b) obtained above can be removed with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.

  The solvent of the reaction mixture containing the compound represented by the formula (1b) obtained above can be distilled off under reduced pressure as long as the compound is not decomposed.

  The reaction mixture containing the compound represented by the formula (1b) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the objective purity.

[Production method C]

  In the formula, SR represents a sulfurizing agent, and R1, R2, R3, Y and n are as defined above.

  The production method C is a production method for obtaining a compound represented by the formula (1b-c) among the compounds represented by the formula (1b), wherein the compound represented by the formula (1b-b) is sulfurized. A production method comprising reacting an agent (SR) in a solvent.

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

  The amount of the sulfurizing agent used in this reaction may be at least 0.5 equivalent to the compound represented by the formula (1b-b), and is not particularly limited as long as the desired reaction proceeds. However, it is preferably 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, and ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane; Benzene-based solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene are exemplified. These solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio.

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

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

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

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

  The reaction mixture containing the compound represented by the formula (1b-c) obtained above can be evaporated under reduced pressure as long as the compound is not decomposed.

  The reaction mixture containing the compound represented by the formula (1b-c) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the objective purity.

[Production method D]

  In the formula, R3a 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 Represents a C2 to C6 alkenyl group optionally substituted by C, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group optionally substituted by a substituent C, or a C2 to C6 haloalkynyl group. , Lv, R1, R2, X, Y and n are as defined above.

  In the production method D, among the compounds represented by the formula (1b), R3a is appropriately substituted with a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, or a substituent C, which may be appropriately substituted with a substituent C. A C3-C8 cycloalkyl group, a C2-C6 alkenyl group optionally substituted with a substituent C, a C2-C6 haloalkenyl group, a C2-C6 group optionally substituted with a substituent C A method for synthesizing a compound represented by the formula (1b-e), which is an alkynyl group or a C2 to C6 haloalkynyl group, wherein the compound represented by the formula (1b-d) and R3a-Lv are Is a reaction method in the presence of a solvent in a solvent.

  R3a-Lv used in this reaction can be obtained as a commercial product or can be produced by a known method.

  The amount of R3a-Lv used in this reaction may be at least 1 equivalent to the compound represented by the formula (1b-d), and is not particularly limited as long as the desired reaction proceeds. Preferably, it is 1 equivalent or more and 1.8 equivalents or less.

  Examples of the base 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 at least 1 equivalent to the compound represented by the formula (1b-d), and is not particularly limited as long as the desired reaction proceeds, but is preferably Is 1 equivalent or more and 10 equivalents or less.

  The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, and ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane; Benzene-based solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene are exemplified. These solvents can be used alone or as a mixture of two or more kinds at an arbitrary 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 times or more and 200 times or more the compound represented by the formula (1b-d). It is as follows.

  The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually from -80 ° 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 an appropriate aqueous solution to the reaction mixture. When an aqueous solution is used, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, or the like is dissolved, thiosulfate An aqueous solution or salt solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved can be used arbitrarily. During the liquid separation operation, if necessary, a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene, an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate, diethyl ether, diisopropyl ether, or methyl- It is possible to add a solvent which is not compatible with water, such as an ether solvent such as t-butyl ether, a halogen solvent such as dichloromethane, dichloroethane and chloroform, and a hydrocarbon solvent such as hexane, heptane, cyclohexane and methylcyclohexane. It is possible. In addition, these solvents can be used alone or as a mixture of two or more kinds at an arbitrary 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 (1b-e) obtained above can be removed with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.

  The reaction mixture containing the compound represented by the formula (1b-e) obtained above can be evaporated under reduced pressure as long as the compound is not decomposed.

  The reaction mixture containing the compound represented by the formula (1b-e) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the objective purity.

[Production method E]

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

  The production method E is a method for obtaining a compound represented by the formula (1a), and comprises reacting a compound represented by the formula (1b) with an oxidizing agent (Ox) in a solvent. is there.

  Examples of the oxidizing agent used in this reaction include metal oxides such as manganese dioxide, benzoquinones such as 2,3-dichloro-5,6-dicyano-p-benzoquinone, azobisisobutyronitrile, benzoyl peroxide and the like. A radical initiator 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 or the like can be used.

  Hereinafter, a method in which the oxidizing agent is a metal oxide will be described.

  The amount of the oxidizing agent used in this reaction is not particularly limited as long as the desired reaction proceeds, as long as it is at least 1 equivalent to the compound represented by the formula (1b). It is equal to or more than 200 equivalents.

  The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene, dichloromethane, dichloroethane, chloroform, Examples include a halogen-based solvent such as carbon tetrachloride. These solvents can be used alone or as a mixture of two or more kinds at an arbitrary 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 by weight based on the compound represented by the formula (1b). is there.

  The temperature at which this reaction is performed 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, undissolved metals can be removed by filtration. Furthermore, a liquid separation operation can be performed by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, or the like is dissolved, or a saline solution Etc. can be used arbitrarily. During the liquid separation operation, if necessary, a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene, an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate, diethyl ether, diisopropyl ether, or methyl- Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane. It is possible to add. In addition, these solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield. In this reaction, a liquid separation operation is not essential.

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

  The reaction mixture containing the compound represented by the formula (1a) obtained above can be distilled under reduced pressure as long as the compound is not decomposed.

  The reaction mixture containing the compound represented by the formula (1a) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the objective purity.

  Hereinafter, a method in which the oxidizing agent is a benzoquinone will be described.

  The amount of the oxidizing agent used in this reaction is not particularly limited as long as the desired reaction proceeds, as long as it is at least 1 equivalent to the compound represented by the formula (1b). It is equal to or more than 20 equivalents.

  The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene, dichloromethane, dichloroethane, chloroform, Examples include a halogen-based solvent such as carbon tetrachloride. These solvents can be used alone or as a mixture of two or more kinds at an arbitrary 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 by weight based on the compound represented by the formula (1b). is there.

  The temperature at which this reaction is performed 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 an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, or the like is dissolved, or a saline solution Etc. can be used arbitrarily. During the liquid separation operation, if necessary, a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene, an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate, diethyl ether, diisopropyl ether, or methyl- Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane. It is possible to add. In addition, these solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield. In this reaction, a liquid separation operation is not essential.

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

  The reaction mixture containing the compound represented by the formula (1a) obtained above can be distilled under reduced pressure as long as the compound is not decomposed.

  The reaction mixture containing the compound represented by the formula (1a) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the objective purity.

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

  When the amounts of the radical initiator and the halogenating agent used in the present reaction are 0.01 equivalent or more and 1.0 equivalent or more with respect to the compound represented by the formula (1b), the desired reaction proceeds. There is no particular limitation as far as it is concerned. Preferably, the amount of the radical initiator is from 0.01 to 1 equivalent, and the amount of the halogenating agent is from 1 to 3 equivalents.

  The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is preferably a halogenated benzene solvent such as chlorobenzene or dichlorobenzene, or an ester solvent such as ethyl acetate, isopropyl acetate or butyl acetate. Solvents include halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane. These solvents can be used alone or as a mixture of two or more kinds at an arbitrary 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 by weight based on the compound represented by the formula (1b). is there.

  The temperature at which this reaction is performed 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 an appropriate aqueous solution to the reaction mixture. When an aqueous solution is used, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, or the like is dissolved, thiosulfate An aqueous solution or salt solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved can be used arbitrarily. During the liquid separation operation, if necessary, a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene, an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate, diethyl ether, diisopropyl ether, or methyl- It is possible to add a solvent which is not compatible with water, such as an ether solvent such as t-butyl ether, a halogen solvent such as dichloromethane, dichloroethane and chloroform, and a hydrocarbon solvent such as hexane, heptane, cyclohexane and methylcyclohexane. It is possible. In addition, these solvents can be used alone or as a mixture of two or more kinds at an arbitrary 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 (1a) obtained above can be removed with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.

  The reaction mixture containing the compound represented by the formula (1a) obtained above can be distilled under reduced pressure as long as the compound is not decomposed.

  The reaction mixture containing the compound represented by the formula (1a) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the objective purity.

[Production method F]

  In the formula, R3b represents a halogen atom, HalR represents a halogenating agent, and R1, R2, X, Y and n are as defined above.

  Production method F is a method for obtaining a compound represented by the formula (1a-b) in which R3b represents a halogen atom among the compounds represented by the formula (1a). And a halogenating agent (HalR) in a solvent.

  Examples of the halogenating agent used in this reaction include selectrofluor (N-fluoro-N′-triethylenediaminebis (tetrafluoroborate)), N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, , 3-dichloro-5,5-dimethylhydantoin, 1,3-dibromo-5,5-dimethylhydantoin, 1,3-diiodo-5,5-dimethylhydantoin, bromine, iodine and the like.

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

When the halogenating agent used in this reaction is an iodination 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 is added. Can be.
When the amount of the acid used when the halogenating agent used in this reaction is an iodizing agent is 0.01 equivalent or more with respect to the compound represented by the formula (1a-a), the desired reaction can be achieved. There is no particular limitation as long as it proceeds, but it is preferably 0.1 equivalent or more and 3 equivalents or less.

  The solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but acidic solvents such as sulfuric acid, acetic acid, trifluoroacetic acid, methanesulfonic acid, and trifluoromethanesulfonic acid, and diethyl ether , Diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, etc., ether solvents, methanol, ethanol, isopropanol, etc. alcohol solvents, benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, etc. benzene solvents. 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; , 3-dimethyl-2-urea-based solvent-imidazolidinone, dichloromethane, dichloroethane, chloroform, and halogen solvents such as carbon tetrachloride. These solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio.

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

  The temperature at which this reaction is performed 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 an appropriate aqueous solution to the reaction mixture. When an aqueous solution is used, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, or the like is dissolved, thiosulfate An aqueous solution or salt solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved can be used arbitrarily. During the liquid separation operation, if necessary, a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene, an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate, diethyl ether, diisopropyl ether, or methyl- Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane. It is possible to add. In addition, these solvents can be used alone or as a mixture of two or more kinds at an arbitrary 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 (1a-b) obtained above can be removed with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.

  The solvent of the reaction mixture containing the compound represented by the formula (1a-b) obtained above can be distilled off under reduced pressure as long as the compound is not decomposed.

  The reaction mixture containing the compound represented by the formula (1a-b) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the objective purity.

[Production method G]

  In the formula, J represents an oxygen atom or a sulfur atom. When J is an oxygen atom, R3c represents a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, or a substituent C, which may be appropriately substituted with a substituent C. A C3-C8 cycloalkyl group optionally substituted, a C2-C6 alkenyl group optionally substituted with a substituent C, a C2-C6 haloalkenyl group, a C2 optionally substituted with a substituent C Represents a C6 to alkynyl group or a C2 to C6 haloalkynyl group, and when J is a sulfur atom, R3c represents a C1 to C6 alkyl group or a C1 to C6 haloalkyl group; and Q represents a hydrogen atom or a metal. , R1, R2, R3b, X, Y and n are as defined above.

  In the production method G, among the compounds represented by the formula (1a), J represents an oxygen atom or a sulfur atom, and when J is an oxygen atom, R3c may be a substituent C1 to C6 which may be appropriately substituted with a substituent C. Alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group optionally substituted with substituent C, C2-C6 alkenyl group optionally substituted with substituent C, C2-C6 halo Represents an alkenyl group, a C2-C6 alkynyl group optionally substituted with a substituent C, or a C2-C6 haloalkynyl group, and when J is a sulfur atom, R3c represents a C1-C6 alkyl group or C1-C6. A method for synthesizing a compound represented by the formula (1a-c), which represents a haloalkyl group represented by the formula (1a-b), wherein the compound represented by the formula (1a-b) and R3c-JQ are Reaction in solvent Is a manufacturing method comprising obtained by coupling reaction to.

  In the compound represented by the formula (1a-b), preferred R3b is a chlorine atom, a bromine atom, or an iodine atom.

  R3c-JQ used in this reaction can be obtained as a commercial product or can be produced by a known method. Preferred Q is a hydrogen atom or an alkali metal such as sodium or potassium.

  The amount of R3c-JQ used in this reaction is not particularly limited as long as the desired reaction proceeds, as long as the amount of the compound represented by the formula (1a-b) is at least one equivalent. . When Q is a hydrogen atom, it can be used also as a solvent.

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

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

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

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

  The base used in this reaction is an inorganic base such as sodium carbonate, potassium carbonate or cesium carbonate, or an organic base such as triethylamine, tributylamine or diisopropylethylamine.

  The amount of the base used in this reaction is not particularly limited as long as the desired reaction proceeds, as long as it is at least 1 equivalent to the compound represented by the formula (1a-b), but is preferably 1 to 50 equivalents.

  The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but R3c-JH (wherein R3c 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, and benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene. Is mentioned. These solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio.

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

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

  As a post-treatment of the reaction, a liquid separation operation can be performed by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, or the like is dissolved, or a saline solution Etc. can be used arbitrarily. During the liquid separation operation, if necessary, a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene, an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate, diethyl ether, diisopropyl ether, or methyl- Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane. It is possible to add. In addition, these solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield. It is also possible, but not essential, to remove insolubles by performing a filtration operation.

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

  The solvent of the reaction mixture containing the compound represented by the formula (1a-c) obtained above can be distilled off under reduced pressure as long as the compound is not decomposed.

  The reaction mixture containing the compound represented by the formula (1a-c) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the objective purity.

[Production method H]

  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 C Represents an optionally substituted C2-C6 alkenyl group or a C2-C6 haloalkenyl group, R3d-B represents an organic boronic acid, and R1, R2, R3b, X, Y and n are as defined above. It is.

  In the production method H, among the compounds represented by the formula (1a), R3d is appropriately substituted with a C1 to C6 alkyl group, C1 to C6 haloalkyl group, or a substituent C, which may be appropriately substituted with a substituent C. A C3-C8 cycloalkyl group, a C2-C6 alkenyl group optionally substituted with a substituent C, or a C2-C6 haloalkenyl group represented by the formula (1a-d). A synthesis method, wherein the compound represented by the formula (1a-b) and an organic boronic acid (R3d-B) are obtained by Suzuki-Miyaura coupling in which a reaction is performed in a solvent in the presence of a transition metal and a base. The manufacturing method includes:

  In formula (1a-b), preferred R3b is a chlorine atom, a bromine atom, or an iodine atom.

  R3d-B used in this reaction represents an organic boronic acid such as an organic boronic acid or an organic boronic ester, and can be obtained as a commercial product or can be produced by a known method.

  The amount of R3d-B used in this reaction is not particularly limited as long as the target reaction proceeds, provided that the amount of R3d-B is at least 1 equivalent to the compound represented by the formula (1a-b). Preferably, it is 1 equivalent or more and 10 equivalents or less.

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

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

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

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

  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 and potassium t-butoxide.

  The amount of the base used in this reaction is not particularly limited as long as the desired reaction proceeds, as long as it is at least 1 equivalent to the compound represented by the formula (1a-b), but is preferably 1 to 50 equivalents.

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

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

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

  As a post-treatment of the reaction, a liquid separation operation can be performed by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, or the like is dissolved, or a saline solution Etc. can be used arbitrarily. During the liquid separation operation, if necessary, a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene, an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate, diethyl ether, diisopropyl ether, or methyl- Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane. It is possible to add. In addition, these solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield. It is also possible, but not essential, to remove insolubles by performing a filtration operation.

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

  The reaction mixture containing the compound represented by the formula (1a-d) obtained above can be distilled off under reduced pressure as long as the compound is not decomposed.

  The reaction mixture containing the compound represented by the formula (1a-d) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the objective purity.

[Manufacturing method I]

  In the formula, R3e represents a C2-C6 alkynyl group or a C2-C6 haloalkynyl group optionally substituted with a substituent C, and R1, R2, R3b, X, Y and n are as defined above. .

  In the production method I, among the compounds represented by the formula (1a), R3e is a C2 to C6 alkynyl group optionally substituted with a substituent C or a C2 to C6 haloalkynyl group. e) a method for synthesizing a compound represented by (e), wherein the compound represented by (1a-b) and a terminal alkyne compound are reacted in a solvent in the presence of a transition metal and a base by Sonogashira coupling. And a manufacturing method including obtaining.

  In formula (1a-b), preferred R3b 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 can be produced by a known method. Further, trimethylsilylacetylene can also be used as the terminal alkyne compound. In this case, it is necessary to introduce a trimethylsilylethynyl group into the compound represented by the formula (1a-b) and then perform desilylation. For desilylation, see Journal of the American Chemical Society, Vol. 131, No. 2, pp. 634-643 (2009). And Journal of Organometallic Chemistry, 696, 25, pp. 4039-4045 (2011). And the like.

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

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

  The amount of the transition metal used in the present reaction may be such that the palladium or the like and the copper are 0.001 equivalent or more with respect to the compound represented by the formula (1a-b), respectively. There is no particular limitation as long as it is done. Preferred amounts are 0.001 equivalent to 1 equivalent in both cases.

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

  The amount of the base used in this reaction is not particularly limited as long as the desired reaction proceeds, as long as it is at least 1 equivalent to the compound represented by the formula (1a-b), but is preferably 1 to 50 equivalents. In addition, an organic base in a liquid state can be used as a solvent.

  A phosphine ligand such as tri-t-butylphosphine or 2-dicyclohexylphosphino-2′4′6′-triisopropylbiphenyl can be added for efficiently proceeding this reaction, but is not essential. .

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

  The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, and 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 , Amide solvents such as N, N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, halogen solvents such as dichloromethane, dichloroethane, chloroform, carbon tetrachloride, triethylamine, triethylamine and the like. Ethylamine, isopropylamine, diethylamine, diisopropylamine, organic amine solvents such as diisopropylethylamine. These solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio.

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

  The temperature at which this reaction is performed 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 an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, or the like is dissolved, or a saline solution Etc. can be used arbitrarily. During the liquid separation operation, if necessary, a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene, an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate, diethyl ether, diisopropyl ether, or methyl- Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane. It is possible to add. In addition, these solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield. It is also possible, but not essential, to remove insolubles by performing a filtration operation.

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

  The reaction mixture containing the compound represented by the formula (1a-e) obtained above can be evaporated under reduced pressure as long as the compound is not decomposed.

  The reaction mixture containing the compound represented by the formula (1a-e) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the objective purity.

[Production method J]

  In the formula, R2a represents a C1 to C6 alkoxy group, nb represents an integer of 0 to 4 (however, when nb is 2 or more, 2 or more R2 represents an independent substituent), and R1 , R2, R3, X, Y and the broken line have the same meanings as described above.

  Production method J is a method for synthesizing a compound represented by the formula (1-b) having a hydroxyl group among the compounds represented by the formula (1), wherein R2a is a C1-C6 alkoxy group. This is a production method comprising obtaining the compound represented by 1-a) and an acid in a solvent.

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

  The amount of the acid used in this reaction may be at least 1 equivalent to the compound represented by the formula (1-a), and is not particularly limited as long as the desired reaction proceeds, but is preferably Is 1 equivalent or more and 10 equivalents or less.

  The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene, and nitrile solvents such as acetonitrile. Halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane. These solvents can be used alone or as a mixture of two or more kinds at an arbitrary 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 times or more and 200 times or more the weight of the compound represented by the formula (1-a). It is as follows.

  The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually from -80 ° 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 an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, or the like is dissolved, or a saline solution Etc. can be used arbitrarily. During the liquid separation operation, if necessary, a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene, an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate, diethyl ether, diisopropyl ether, or methyl- Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane. It is possible to add. In addition, these solvents can be used alone or as a mixture of two or more kinds at an arbitrary 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 (1-b) obtained above can be removed with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.

  The reaction mixture containing the compound represented by the formula (1-b) obtained above can be distilled under reduced pressure as long as the compound is not decomposed.

  The reaction mixture containing the compound represented by the formula (1-b) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the objective purity.

[Production method K]

  In the formula, R2b is a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with a substituent B, a substituent A C2-C6 alkenyl group optionally substituted with B, a C2-C6 haloalkenyl group, a C3-C6 alkynyl group optionally substituted with a substituent B, a C3-C6 haloalkynyl group, or R20C (＝ O) — represents a group, and Lv, R1, R2, R3, R20, X, Y, nb and a broken line part are as defined above.

  In the production method K, among the compounds represented by the formula (1), R2b-O- is a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group, and a substituent which may be appropriately substituted with the substituent B. C3 to C8 cycloalkoxy group optionally substituted by B, C2 to C6 alkenyloxy group optionally substituted by substituent B, C2 to C6 haloalkenyloxy group, optionally substituted by substituent B A C3 to C6 alkynyloxy group, a C3 to C6 haloalkynyloxy group, or a R20C (） O) O— group (R20 has the same meaning as described above); Which is a method for synthesizing a compound represented by the formula (1-b) and R2b-Lv in a solvent in the presence of a base.

  R2b-Lv used in this reaction can be obtained as a commercial product or can be produced by a known method.

  R2b-Lv used in this reaction may be at least 1 equivalent to the compound represented by the formula (1-b), and is not particularly limited as long as the desired reaction proceeds, but is preferably Is 1 equivalent or more and 10 equivalents or less.

  Examples of the base 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, lutidine, and the like. However, there is no particular limitation as long as the desired reaction proceeds.

  The base used in this reaction may be at least 1 equivalent to the compound represented by the formula (1-b), and is not particularly limited as long as the desired reaction proceeds. It is 1 equivalent or more and 10 equivalents or less.

  The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, and 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; and nitrile solvents such as acetonitrile; Amide solvents such as N-methylpyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, dichloromethane, dichloroethane, chloroform Holm, halogenated solvents such as carbon tetrachloride, dimethyl sulfoxide, sulfur-based solvents such as sulfolane, acetone, methyl ethyl ketone, ketone solvents such as methyl isobutyl ketone. These solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio.

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

  The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually -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 an appropriate aqueous solution to the reaction mixture. When an aqueous solution is used, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, or the like is dissolved, thiosulfate An aqueous solution or salt solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved can be used arbitrarily. During the liquid separation operation, if necessary, a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene, an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate, diethyl ether, diisopropyl ether, or methyl- Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane. It is possible to add. In addition, these solvents can be used alone or as a mixture of two or more kinds at an arbitrary 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 (1-c) obtained above can be removed with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.

  The solvent of the reaction mixture containing the compound represented by the formula (1-c) obtained above can be distilled off under reduced pressure as long as the compound is not decomposed.

  The reaction mixture containing the compound represented by the formula (1-c) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the objective purity.

[Production method L]

  In the formula, R2c represents a halogen atom, and R2d represents a C1 to C6 alkyl group, a C1 to C6 haloalkyl group optionally substituted with the substituent B, a C3 to C8 optionally substituted with the substituent B. A cycloalkyl group, a C2 to C6 alkenyl group optionally substituted with a substituent B, or a C2 to C6 haloalkenyl group, R2d-B represents an organic boronic acid, and R1, R2, R3, nb, X, Y and the broken line part are as defined above.

  In the production method L, among the compounds represented by the formula (1), R2d is appropriately substituted with a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, or a substituent B, which may be appropriately substituted with a substituent B. A C3-C8 cycloalkyl group, a C2-C6 alkenyl group optionally substituted with a substituent B, or a C2-C6 haloalkenyl group represented by the formula (1-e): A synthesis method, wherein the compound represented by the formula (1-d) and an organic boronic acid (R2d-B) are obtained by a Suzuki-Miyaura coupling in which a reaction is performed in a solvent in the presence of a transition metal and a base. The manufacturing method includes:

  In the compound represented by the formula (1-d), preferred R2c is a chlorine atom, a bromine atom, or an iodine atom.

  By using the compound represented by the formula (1a-b) and R3d-B in the production method H in place of the compound represented by the formula (1-d) and R2d-B, respectively, the production method H The manufacturing method L can be performed according to

[Manufacturing method M]

  In the formula, R2e represents a C2 to C6 alkynyl group or a C2 to C6 haloalkynyl group which may be appropriately substituted with the substituent B, and R1, R2, R2c, R3, nb, X, Y and a broken line part It is the same as the above.

  In the production method M, among the compounds represented by the formula (1), R2e is a C2 to C6 alkynyl group optionally substituted with a substituent B or a C2 to C6 haloalkynyl group. A method for synthesizing a compound represented by f), comprising obtaining the compound represented by formula (1-d) by Sonogashira coupling with a terminal alkyne compound.

  In the compound represented by the formula (1-d), preferred R2c is a chlorine atom, a bromine atom, or an iodine atom.

  By using the compound represented by the formula (1a-b) in the production method I instead of the compound represented by the formula (1-d), the production method M can be carried out according to the production method I. .

[Manufacturing method N]

  In the formula, Da represents a halogen atom, D1a represents a halogen atom, D1b represents a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group, or a C3 to C8 cycloalkoxy group, and E represents a halogen atom. Represents a substituted carbon atom or a nitrogen atom, and R1, R2, R3, n, X, Q and a broken line part are as defined above.

  In the production method N, among the compounds represented by the formula (1), D1b is a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group, or a C3 to C8 cycloalkoxy group, and E is a halogen atom. A method for synthesizing a compound represented by the formula (1-h), which is a substituted carbon atom or a nitrogen atom, comprising reacting a compound represented by the formula (1-g) with D1b-Q in the presence of a base. And a reaction in a solvent.

  D1b-Q used in this reaction can be obtained as a commercial product or can be produced by a known method. Preferred Q is a hydrogen atom or an alkali metal such as sodium or potassium.

  The amount of D1b-Q used in this reaction is not particularly limited as long as the target reaction proceeds as long as the amount of D1b-Q is at least 1 equivalent to the compound represented by the formula (1-g). Preferably, it is 1 equivalent or more and 30 equivalents or less. When Q represents a hydrogen atom, it can be used as a solvent.

  The base used in this reaction is preferably an inorganic base such as sodium carbonate, potassium carbonate, cesium carbonate, and sodium hydride. 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 the desired reaction proceeds, as long as it is at least 1 equivalent to the compound represented by the formula (1-g). It is 1 equivalent or more and 30 equivalents or less.

  The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but an alcoholic solvent represented by D1b-H (where D1b has the same meaning as described above), Ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran and dioxane; benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene; ethyl acetate, isopropyl acetate and butyl acetate Ester solvents such as acetonitrile; amide solvents such as N-methylpyrrolidone, N, N-dimethylformamide and N, N-dimethylacetamide; and 1,3-dimethyl-2-imidazolidinone. Urea solvents, dichloromethane, dichloro Tan, chloroform, halogenated solvents such as carbon tetrachloride, dimethyl sulfoxide, sulfur-based solvents such as sulfolane, acetone, methyl ethyl ketone, ketone solvents such as methyl isobutyl ketone. These solvents can be used alone or as a mixture of two or more kinds at an arbitrary 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 by weight based on the compound represented by the formula (1-g). It is as follows.

  The temperature at which this reaction is performed 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 an appropriate aqueous solution to the reaction mixture. When an aqueous solution is used, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, or the like is dissolved, thiosulfate An aqueous solution or salt solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved can be used arbitrarily. During the liquid separation operation, if necessary, a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene, an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate, diethyl ether, diisopropyl ether, or methyl- Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane. It is possible to add. In addition, these solvents can be used alone or as a mixture of two or more kinds at an arbitrary 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 (1-h) obtained above can be removed with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.

  The reaction mixture containing the compound represented by the formula (1-h) obtained above can be distilled under reduced pressure as long as the compound is not decomposed.

  The reaction mixture containing the compound represented by the formula (1-h) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the objective purity.

[Production method O]

  In the formula, R2e represents a C1 to C6 alkoxy group optionally substituted with a substituent B, R2f represents a C1 to C6 alkoxy group optionally substituted with a substituent B, and R2g represents a halogen atom. In the formula, HalR, R1, R3, X, Y and the broken line have the same meanings as described above.

  In the production method O, among the compounds represented by the formula (1), R2e is a C1 to C6 alkoxy group optionally substituted with the substituent B, and R2f may be appropriately substituted with the substituent B. A method for producing a compound represented by the formula (1-j), which is a C1 to C6 alkoxy group and R2g is a halogen atom, wherein the compound represented by the formula (1-i) and a halogenating agent ( HalR) in a solvent.

  Examples of the halogenating agent used in this reaction include selectrofluor (N-fluoro-N′-triethylenediaminebis (tetrafluoroborate)), N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, , 3-dichloro-5,5-dimethylhydantoin, 1,3-dibromo-5,5-dimethylhydantoin, 1,3-diiodo-5,5-dimethylhydantoin, bromine, iodine and the like.

  The amount of the halogenating agent used in this reaction is not particularly limited as long as the desired reaction proceeds, provided that the amount of the halogenating agent is at least 1 equivalent to the compound represented by the formula (1-i). Preferably, it is 1 equivalent or more and 10 equivalents or less. However, the amount of the halogenating agent containing hydantoin is not particularly limited as long as the desired reaction proceeds as long as the amount is 0.5 equivalent or more, and is preferably 1 equivalent to 5 equivalents.

  When the halogenating agent used in this reaction is an iodizing 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 is added. Can be.

  When the amount of the acid used when the halogenating agent used in this reaction is an iodizing agent is 0.01 equivalent or more with respect to the compound represented by the formula (1-i), the desired reaction can be achieved. There is no particular limitation as long as it proceeds, but it is preferably 0.1 equivalent or more and 3 equivalents or less.

  The solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but acidic solvents such as sulfuric acid, acetic acid, trifluoroacetic acid, methanesulfonic acid, and trifluoromethanesulfonic acid, and diethyl ether , Diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, etc., ether solvents, methanol, ethanol, isopropanol, etc. alcohol solvents, benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, etc. benzene solvents. 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; , 3-dimethyl-2-urea-based solvent-imidazolidinone, dichloromethane, dichloroethane, chloroform, and halogen solvents such as carbon tetrachloride. These solvents can be used alone or as a mixture of two or more kinds at an arbitrary 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 times or more and 200 times or more the compound represented by the formula (1-i). It is as follows.

  The temperature at which this reaction is performed 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 an appropriate aqueous solution to the reaction mixture. When an aqueous solution is used, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, or the like is dissolved, thiosulfate An aqueous solution or salt solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved can be used arbitrarily. During the liquid separation operation, if necessary, a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene, an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate, diethyl ether, diisopropyl ether, or methyl- Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane. It is possible to add. In addition, these solvents can be used alone or as a mixture of two or more kinds at an arbitrary 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 (1-j) obtained above can be removed with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.

  The reaction mixture containing the compound represented by the formula (1-j) obtained above can be distilled under reduced pressure as long as the compound is not decomposed.

  The reaction mixture containing the compound represented by the formula (1-j) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the objective purity.

[Manufacturing method P]

  In the formula, Da represents a halogen atom, D1a represents a halogen atom, D2a represents a cyano group, a C2 to C6 alkenyloxy group optionally substituted with a substituent B, a C2 to C6 haloalkenyloxy group, A C3-C6 alkynyloxy group optionally substituted with group B, a C3-C6 haloalkynyloxy group, a C2-C6 alkoxyalkoxy group optionally substituted with substituent B, a C2-C6 cyanoalkoxy Group, C4-C9 cycloalkylalkoxy group, heteroaryl group optionally substituted with substituent D, aryloxy group optionally substituted with substituent D, hetero optionally substituted with substituent D Aryloxy group, aralkyloxy group optionally substituted with substituent D, R40 (CH2) pU-group, R41R42N- group, R43 L4 and R47R48C = N-O-; E represents a carbon atom or a nitrogen atom substituted with a halogen atom; R1, R2, R3, n, X, Q, R40, p, U, R41 , R42, R43, L4, R47, R48 and the broken line part are as defined above.

  In the production method P, among the compounds represented by the formula (1), D2a is a cyano group, a C2 to C6 alkenyloxy group optionally substituted with a substituent B, a C2 to C6 haloalkenyloxy group, A C3-C6 alkynyloxy group optionally substituted with a substituent B, a C3-C6 haloalkynyloxy group, a C2-C6 alkoxyalkoxy group optionally substituted with a substituent B, a C2-C6 cyano An alkoxy group, a C4 to C9 cycloalkylalkoxy group, a heteroaryl group optionally substituted with a substituent D, an aryloxy group optionally substituted with a substituent D, and optionally substituted with a substituent D A heteroaryloxy group, an aralkyloxy group optionally substituted with a substituent D, an R40 (CH2) p-U- group, an R41R42N- group, an R43-L4- group, And R47R48C = N—O—, wherein E is a compound represented by the formula (1-k), which is a carbon atom or a nitrogen atom substituted with a halogen atom, wherein the compound represented by the formula (1-g) And D2a-Q in a solvent in the presence of a base.

  D2a-Q used in this reaction can be obtained as a commercial product or can be produced by a known method. Desirable Q is a hydrogen atom or an alkali metal such as sodium or potassium.

  The amount of D2a-Q used in this reaction is not particularly limited as long as the desired reaction proceeds, provided that the amount of D2a-Q is at least 1 equivalent to the compound represented by the formula (1-g). Preferably, it is 1 equivalent or more and 30 equivalents or less. When Q represents a hydrogen atom, it can be used as a solvent.

  The base used in this reaction is preferably an inorganic base such as sodium carbonate, potassium carbonate, cesium carbonate, and sodium hydride. 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 the desired reaction proceeds, provided that the amount of the base is at least 1 equivalent to the compound represented by the formula (1-g). And 1 to 30 equivalents.

  The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but an alcohol solvent represented by D2a-H (where D2a has the same meaning as described above), Ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran and dioxane; benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene; ethyl acetate, isopropyl acetate and butyl acetate Ester solvents such as acetonitrile; amide solvents such as N-methylpyrrolidone, N, N-dimethylformamide and N, N-dimethylacetamide; and 1,3-dimethyl-2-imidazolidinone. Urea solvents, dichloromethane, dichloro Tan, chloroform, halogenated solvents such as carbon tetrachloride, dimethyl sulfoxide, sulfur-based solvents such as sulfolane, acetone, methyl ethyl ketone, ketone solvents such as methyl isobutyl ketone. These solvents can be used alone or as a mixture of two or more kinds at an arbitrary 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 by weight based on the compound represented by the formula (1-g). It is as follows.

  The temperature at which this reaction is performed 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 an appropriate aqueous solution to the reaction mixture. When an aqueous solution is used, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, or the like is dissolved, thiosulfate An aqueous solution or salt solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved can be used arbitrarily. During the liquid separation operation, if necessary, a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene, an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate, diethyl ether, diisopropyl ether, or methyl- Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane. It is possible to add. In addition, these solvents can be used alone or as a mixture of two or more kinds at an arbitrary 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 (1-k) obtained above can be removed with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.

  The solvent of the reaction mixture containing the compound represented by the formula (1-k) obtained as described above can be distilled off under reduced pressure as long as the compound is not decomposed.

  The reaction mixture containing the compound represented by the formula (1-k) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the objective purity.

[Production method Q]

  In the formula, D1c represents a C1 to C6 alkoxy group, and R1, R2, R3, Da, X, E, n and a broken line have the same meanings as described above.

  The production method Q is a method for synthesizing a compound represented by the formula (1-m) having a hydroxyl group among the compounds represented by the formula (1), wherein D1c is a C1-C6 alkoxy group. This is a production method comprising obtaining the compound represented by 1-1) and an acid in a solvent.

  Examples of the acid used in this reaction include inorganic acids such as hydrochloric acid and sulfuric acid, organic acids such as acetic acid, trifluoroacetic acid, methanesulfonic acid, and trifluoromethanesulfonic acid, and boron halides such as boron trichloride and boron tribromide. An acid such as can be added.

  The amount of the acid used in this reaction may be at least 1 equivalent to the compound represented by the formula (1-1), and is not particularly limited as long as the desired reaction proceeds, but is preferably Is 1 equivalent or more and 10 equivalents or less.

  The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is not limited to sulfuric acid, acetic acid, trifluoroacetic acid, methanesulfonic acid, an acidic solvent such as trifluoromethanesulfonic acid, benzene, Benzene solvents such as toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene, nitrile solvents such as acetonitrile, halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbons such as hexane, heptane, cyclohexane and methylcyclohexane System solvents and the like. These solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio.

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

  The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually from -80 ° 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 an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, or the like is dissolved, or a saline solution Etc. can be used arbitrarily. During the liquid separation operation, if necessary, a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene, an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate, diethyl ether, diisopropyl ether, or methyl- Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane. It is possible to add. In addition, these solvents can be used alone or as a mixture of two or more kinds at an arbitrary 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 (1-m) obtained above can be removed with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.

  The solvent of the reaction mixture containing the compound represented by the formula (1-m) obtained above can be distilled off under reduced pressure as long as the compound is not decomposed.

  The reaction mixture containing the compound represented by the formula (1-m) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the objective purity.

[Production method R]

In the formula, D2b is a C3-C8 cycloalkyl group optionally substituted with a substituent A, a C2-C6 alkenyl group optionally substituted with a substituent B, a C2-C6 haloalkenyl group, A C3 to C6 alkynyl group optionally substituted by a group B, a C3 to C6 haloalkynyl group, a C2 to C6 alkoxy group optionally substituted by a substituent B, and an optionally substituted substituent D A good aryl group, a heteroaryl group optionally substituted with a substituent D, an R40 (CH2) p- group, and an R44C (= O)-group;
Lv, R1, R2, R3, R40, R44, p, X, Da, E, n, and the broken line have the same meanings as described above.

  In the production method R, among the compounds represented by the formula (1), D2b-O- is a C2 to C6 alkenyloxy group optionally substituted with a substituent B, a C2 to C6 haloalkenyloxy group, A C3-C6 alkynyloxy group optionally substituted with a substituent B, a C3-C6 haloalkynyloxy group, a C2-C6 alkoxyalkoxy group optionally substituted with a substituent B, and a substituent A An optionally substituted C2-C6 cyanoalkoxy group, an optionally substituted C4-C9 cycloalkylalkoxy group optionally substituted with substituent A, an aryloxy group optionally substituted with substituent D, An optionally substituted heteroaryloxy group, an aralkyloxy group optionally substituted with substituent D, an R40 (CH2) pU- group, and an R44C (= O) O- group; A method for synthesizing a compound represented by the formula (1-o), comprising reacting a compound represented by the formula (1-n) with D2b-Lv in a solvent in the presence of a base. Is the way.

  D2b-Lv used in this reaction can be obtained as a commercial product or can be produced by a known method.

  D2b-Lv used in this reaction may be at least 1 equivalent to the compound represented by the formula (1-n), and is not particularly limited as long as the desired reaction proceeds, but is preferably used. Is 1 equivalent or more and 10 equivalents or less.

  Examples of the base 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, lutidine, and the like. However, there is no particular limitation as long as the desired reaction proceeds.

  The base used in this reaction may be at least one equivalent to the compound represented by the formula (1-n), and is not particularly limited as long as the desired reaction proceeds. It is 1 equivalent or more and 10 equivalents or less.

  The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, and 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; and nitrile solvents such as acetonitrile; Amide solvents such as N-methylpyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, dichloromethane, dichloroethane, chloroform Holm, halogenated solvents such as carbon tetrachloride, dimethyl sulfoxide, sulfur-based solvents such as sulfolane, acetone, methyl ethyl ketone, ketone solvents such as methyl isobutyl ketone. These solvents can be used alone or as a mixture of two or more kinds at an arbitrary 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 times or more and 200 times or more the weight of the compound represented by the formula (1-n). It is as follows.

  The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually -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 an appropriate aqueous solution to the reaction mixture. When an aqueous solution is used, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, or the like is dissolved, thiosulfate An aqueous solution or salt solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved can be used arbitrarily. During the liquid separation operation, if necessary, a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene, an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate, diethyl ether, diisopropyl ether, or methyl- Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane. It is possible to add. In addition, these solvents can be used alone or as a mixture of two or more kinds at an arbitrary 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 (1-o) obtained above can be removed with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.

  The reaction mixture containing the compound represented by the formula (1-o) obtained above can be distilled under reduced pressure as long as the compound is not decomposed.

  The reaction mixture containing the compound represented by the formula (1-o) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the objective purity.

[Manufacturing method S]

  In the formula, D2c is a C2-C6 alkenyl group optionally substituted with a substituent B, a C2-C6 haloalkenyl group, an aryl group optionally substituted with a substituent D, and optionally substituted with a substituent D Represents a heteroaryl group which may be substituted, D2c-B represents an organic boronic acid, and R1, R2, R3, n, X, E, Da, D1a and a dashed line part are as defined above.

  In the production method S, among the compounds represented by the formula (1), D2c is appropriately substituted with a C2 to C6 alkenyl group, a C2 to C6 haloalkenyl group and a substituent D, which may be appropriately substituted with the substituent B. A method for synthesizing a compound represented by the formula (1-p), which is an aryl group which may be optionally substituted, and a heteroaryl group which may be optionally substituted by a substituent D, represented by the formula (1-g) It is a production method comprising obtaining the compound by an Suzuki-Miyaura coupling in which a compound is reacted with an organic boronic acid (D2c-B).

  In Formula (1-g), preferred D1a is a chlorine atom, a bromine atom, or an iodine atom.

  By using the compound represented by formula (1a-b) and R3d-B in production method H in place of the compound represented by formula (1-g) and D2c-B, respectively, production method H The manufacturing method S can be performed according to

[Manufacturing method T]

  In the formula, D2d represents a C2 to C6 alkynyl group and a C2 to C6 haloalkynyl group which may be appropriately substituted with the substituent B, and R1, R2, R3, n, X, E, Da, D1a and a broken line The parts are as defined above.

  The production method T is a compound represented by the formula (1-) in which, among the compounds represented by the formula (1), D2d is a C2 to C6 alkynyl group or a C2 to C6 haloalkynyl group optionally substituted with a substituent B. A method for synthesizing a compound represented by q), which comprises obtaining the compound represented by formula (1-g) by Sonogashira coupling with a terminal alkyne compound.

  In the compound represented by the formula (1-g), preferred D1a is a chlorine atom, a bromine atom, or an iodine atom.

  By using the compound represented by the formula (1a-b) in the production method I instead of the compound represented by the formula (1-g), the production method T can be carried out according to the production method I. .

[Manufacturing method U]

In the formula, La represents S, Lb represents SO or SO ₂ , and Ox ′ represents an oxidizing agent.

Production process U is the compound represented by the formula (1), R2, R3, substituent A, substituents B, Lb included in substituents C, and the substituent D2 is SO or SO ₂ wherein (Lb The method for producing a compound represented by the formula (La) wherein, in formula (1), La contained in R 2, R 3, substituent A, substituent B, substituent C, and substituent D 2 is S. ) And an oxidizing agent (Ox ′) in a solvent.

  Examples of the oxidizing agent used in the present reaction include peroxides such as aqueous hydrogen peroxide and meta-chloroperbenzoic acid. Also, transition metals such as sodium tungstate can be added.

The amount of oxidizing agent used in this reaction, to the compound represented by the formula (La) in the manufacture of SO, is usually, 1.0 1.2 equivalents or less equivalent or more, producing SO ₂ In doing so, it is usually 2 equivalents or more and 10 equivalents or less. When adding transition metals, the amount is usually 0.001 equivalent or more and 1 equivalent or less.

  The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but may be an aqueous solvent, an acidic solvent such as acetic acid, benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, or the like. Examples thereof include benzene solvents, nitrile solvents such as acetonitrile, and halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride. These solvents can be used alone or as a mixture of two or more kinds at an arbitrary 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 by weight based on the compound represented by the formula (La). is there.

  The temperature at which this reaction is performed is not particularly limited as long as the desired reaction proceeds, but is usually -10 ° C or more and 120 ° C or less or the boiling point of the solvent or less.

  As a post-treatment of the reaction, a liquid separation operation can be performed by adding water or an appropriate aqueous solution to the reaction mixture. When an aqueous solution is used, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, or the like is dissolved, thiosulfate An aqueous solution or salt solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved can be used arbitrarily. During the liquid separation operation, if necessary, a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene, an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate, diethyl ether, diisopropyl ether, or methyl- Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane. It is possible to add. In addition, these solvents can be used alone or as a mixture of two or more kinds at an arbitrary 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 (Lb) obtained above can be removed with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.

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

  The reaction mixture containing the compound represented by the formula (Lb) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the objective purity.

  Next, a method for synthesizing the compound represented by Formula (3) described in Production Method A will be described.

[Manufacturing method V]

  In the formula, R2, R3, R5, n, X and Y are as defined above.

  The production method V is a method for producing a production intermediate represented by the formula (3), in which a compound represented by the formula (4) and a compound represented by the formula (5) are reacted in the presence of a base. This is a production method including reacting in a solvent.

  The compound represented by the formula (4) used in this reaction can be synthesized according to Reference Examples. Also, Green Chemistry, Vol. 41, pp. 580-585, and The Journal of Organic Chemistry, Vol. 65, No. 20, pp. 6458-6461 (2000). Etc. can be synthesized with reference.

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

  The amount of the compound represented by the formula (5) used in this reaction is not particularly limited as long as the desired reaction proceeds, as long as the amount of the compound represented by the formula (4) is 1 equivalent or more. But not more than 1 equivalent and not more than 3 equivalents.

  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 and potassium t-butoxide.

  The base used in this reaction can be carried out in a catalytic amount, and is not particularly limited as long as the desired reaction proceeds, but is preferably a compound represented by the formula (4). On the other hand, it is 0.01 to 3 equivalents.

  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; acetone, methyl ethyl ketone and methyl ether Ketone solvents such as butyl ketone and the like. These solvents can be used alone or as a mixture of two or more kinds at an arbitrary 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 by weight based on the compound represented by the formula (4). is there.

  The temperature at which this reaction is performed is not particularly limited as long as the desired reaction proceeds, but 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 an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, or the like is dissolved, or a saline solution Etc. can be used arbitrarily. During the liquid separation operation, if necessary, a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene, an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate, diethyl ether, diisopropyl ether, or methyl- Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane. It is possible to add. In addition, these solvents can be used alone or as a mixture of two or more kinds at an arbitrary 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 (3) obtained above can be removed with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.

  The solvent of the reaction mixture containing the compound represented by the formula (3) obtained above can be distilled off under reduced pressure as long as the compound is not decomposed.

  The reaction mixture containing the compound represented by the formula (3) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the objective purity.

[Production method W]

  In the formula, R5a represents a C1 to C6 alkyl group, and R2, R3, n, X, and Y are as defined above.

  The production method W is a method for producing a production intermediate represented by the formula (3b) among the compounds represented by the formula (3), wherein the compound represented by the formula (3a) is prepared under an acidic condition or a base condition. This is a production method comprising reacting in a solvent under ionic conditions.

  First, the reaction under acidic conditions will be described.

  Examples of the acid used in this reaction include inorganic acids such as hydrochloric acid, hydrobromic acid, and phosphoric acid, and organic acids such as acetic acid, methanesulfonic acid, p-toluenesulfonic acid, and trifluoroacetic acid. There is no particular limitation as long as the desired reaction proceeds.

  The amount of the acid used in this reaction may be a catalytic amount, and is not particularly limited as long as the desired reaction proceeds, but is preferably 0.1 to 0.1 with respect to the compound represented by the formula (3a). It is at least 01 equivalent. Further, a liquid acid can be used as a solvent.

  The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds.Aqueous solvents, acetic acid, acidic solvents such as methanesulfonic acid, diethyl ether, diisopropyl ether, methyl-t- Ether solvents such as butyl ether, dimethoxyethane, tetrahydrofuran and dioxane; alcohol solvents such as methanol, ethanol and isopropanol; benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene; ethyl acetate, isopropyl acetate and acetic acid Ester solvents such as butyl, nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, 1,3-dimethyl-2-imidazolidinone Ure System solvent, dichloromethane, dichloroethane, chloroform, and halogen solvents such as carbon tetrachloride. These solvents can be used alone or as a mixture of two or more kinds at an arbitrary 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 by weight based on the compound represented by the formula (3a). is there.

  The temperature at which this reaction is performed 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.
Examples of the base used in this reaction include inorganic bases such as lithium hydroxide, sodium hydroxide, and potassium hydroxide, but are not particularly limited as long as the desired reaction proceeds.

  The base used in this reaction is not particularly limited as long as the desired reaction proceeds, as long as it is at least 1 equivalent to the compound represented by the formula (3a), but is preferably at least 1 equivalent. Not more than 30 equivalents,

  The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but an ether such as a water solvent, diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, etc. Solvent, alcohol solvent such as methanol, ethanol, isopropanol, etc., benzene solvent such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, ester solvent such as ethyl acetate, isopropyl acetate, butyl acetate, etc., nitrile such as acetonitrile Amide solvents such as N-methylpyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, dichloromethane, dichloroethane , Chloroform, and halogen solvents such as carbon tetrachloride. These solvents can be used alone or as a mixture of two or more kinds at an arbitrary 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 by weight based on the compound represented by the formula (3a). is there.

  The temperature at which this reaction is performed is not particularly limited as long as the desired reaction proceeds, but is usually -20 ° C or higher and 180 ° C or lower or the boiling point of the solvent or lower.

  For the post-treatment of the reaction, the reaction under acidic conditions and the reaction under basic conditions can be performed by a common method. Separation operation can be performed by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, or the like is dissolved, or a saline solution Etc. can be used arbitrarily. During the liquid separation operation, if necessary, a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene, an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate, diethyl ether, diisopropyl ether, or methyl- Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane. It is possible to add. In addition, these solvents can be used alone or as a mixture of two or more kinds at an arbitrary 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 (3b) obtained above can be removed with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.

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

  The reaction mixture containing the compound represented by the formula (3b) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the objective purity.

The compound represented by the formula (3b) is represented by the formula (3b ′)

  (Wherein, R2, R3, n, X and Y have the same meanings as described above).

  The compound represented by the formula (3b ′) can be handled in the same manner as the compound represented by the formula (3b), and the production method A can be applied. Further, the compound represented by the formula (3b ') contains an asymmetric carbon, and the isomers may be used alone or in a mixture at an arbitrary ratio. Furthermore, a mixture of the compound represented by the formula (3b) and the compound represented by the formula (3b ′) may be used, and the mixing ratio of the isomers may be singly or a mixture having an arbitrary ratio.

  The compound represented by the formula (1) can be produced by arbitrarily combining the production methods A to W shown above. Alternatively, the compound represented by Formula (1) can be produced by arbitrarily combining a known method with Production Method A to Production Method W.

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

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

  The plant disease referred to in the present invention is a crop, a flower, a flower, a plant such as a tree, wilting, withering, yellowing, atrophy, systemic abnormal pathological symptoms such as stunts, or spots, leaf withering, mosaic. , Partial pathological symptoms such as cigars, wilt, root rot, nodules, nodules and the like. That is, the plant becomes ill. Pathogens causing plant diseases mainly include fungi, bacteria, spiroplasma, phytoplasma, viruses, viroids, parasitic higher plants, nematodes and the like. The compound of the present invention is effective on fungi, but is not limited thereto.

  Diseases caused by fungi are mainly fungal diseases. Fungi (pathogens) that cause fungal diseases include fungus fungi, oomycetes, zygomycetes, ascomycetes, basidiomycetes and incomplete fungi. For example, as fungus fungi, root-knot fungus, powdery mildew fungus, sugar beet wilt fungus, oomycete, downy mildew, Pythium genus, Aphanomyces genus, zygomycetes Rhizopus genus, ascomycetes Fungi include peach leaf blight, corn sesame leaf blight, rice blast, powdery mildew, anthracnose, red mold, bacillus seedling, sclerotium, basidiomycetes, rust, smut, and purple print Fungi, blast fungus, sheath blight fungus, and imperfect fungi include gray mold, Alternaria, Fusarium, Penicillium, Rhizoctonia, and white silk.

  The compound of the present invention is effective against various plant diseases. Hereinafter, specific examples of the disease name and the pathogen name will be shown.

Rice blast (Magnaporthe grisea), sheath blight (Thanatephorus cucumeris), brown rot (Ceratobasidium setariae), brown sclerotium (Waitea circinata), brown spot rot spelling bacterium (Terca erucorus phus) Sclerotium hydrophilum, red rot (Wairea circinata), black rot (Entyloma dactylidis), pneumococcal disease (Magnaporthe salvinii leaf blight, Ceratobosa sigma rot) Blight disease (Sphaerulina oryzina) , Frog seedling disease (Gibberella fujikuroi), seedling blight (Pythium spp., Fusarium spp., Trichoderma spp., Rhizopus spp., Rhizonia spore, Rhizoctonia spore, Rhizoptonia solipani, Ms. Rhizotonia sol. Achlya spp., Dictyuchus spp.), Rice scab (Claviceps virens), Black smut (Tilletia barclayana), Brown rice (Curvularia spp., Alternaria)
spp. ), Yellow dwarf (Sclerophthora macrospora), blight blight (Xanthomonas oryzae pv. Oryzae), brown streak (Acidovorax avenae subsp. Avenae b. ), Birch blight bacterial disease (Burkholderia glumae), leaf sheath browning disease (Pseudomonas fuscovaginae), scab blight (Pseudomonas syringae pv. (Rice strip tenuivirus), dwarf disease (Rice warf reovirus);
Powdery mildew of wheat (Blumeria graminis f.sp.hordei;
f. sp. tritici), rust (Puccinia striiformis,
Puccinia graminis, Puccinia recondita, Puccinia hordei), Madarahabyo (Pyrenophora graminea), net blotch (Pyrenophora teres), Fusarium head blight (Gibberella zeae, Fusarium culmorum, Fusarium avenaceum, Monographella nivalis), snow mold (Typhula incarnata, Typhula ishikariensis, Monographella nivalis, Nastil (Ustilago nuda), Black smut (Tilletia caries, Tilletia conoverversa), Eye spot disease (Pseudocercoler) potrichoides, strain rot (Ceratobasidium gramineum), scald disease (Rynchosporium secalis), leaf blight (Septria tritici), wilt (Phaeophasia p.p. sap, p. phosopia. , Septoria spp., Pyrenophora spp.), Damping-off disease (Gaeumanomyces graminis), Anthrax (Colletotrichum graminicola), Ergot (Clavipes ssp. ringae);
Fusarium avenaceum, Penicillium spp, Pythium spp., Rhizoctonia spp., Pustinia sorghum sorghum, Puccinia sorghum sorghum, Puccinia sorghum blossoms (Puccinia sorghum), and rust (Puccinia sorghum). Ustilago maydis, anthrax (Colletotrichum graminicola), northern leaf spot (Cochliobolus carbumum), brown streak (Acidovorax avenae ssp. Avensp. , Bacterial wilt disease (Erwinia stewartii); downy mildew of grape (Plasmopara viticola), rust (Physopella ampelopsidis), powdery mildew (Uncinula necrota, Elina laurel, Elsinella sclera) Colletotrichum acutatum, black rot (Guignardia bidwellii), vine disease (Phomopsis viticola), soybean spot disease (Zygophiala jamaicenus pedicae disease, blight disease sprouts, Botryaedias blight) mompa), white crest feathers Disease (Rosellinia necatrix), apical carcinoma disease (Agrobacterium vitis); powdery mildew of apples (Podosphaera leucotricha), scab (Venturia inaealia, red leaf sprouts (Alternaria ganaria nymph) Disease (Monilinia mali), rot (Valsa ceratosperma), ring spot (Botryosphaeria berengeriana), anthrax (Colletotrichum actuatum sigma sigma sigma sigma, gomerella singula sigma, swelling) ena), black spot disease (Mycosphaerella pomi), purple root rot (Helicobasidium momba), white root rot (Rosellinia necatrix), blight (Phomopsis mali, Diaporthe tanako papaya tanako papaya) Injury (Erwinia amylovora), Apical carcinoma (Agrobacterium tumefaciens), Hairy root disease (Agrobacterium rhizogenes);
Pear black spot (Alternaria kikuchiana), scab (Venturia nasicola), scab (Gymnosporangium asiaticum), ring spot (Botryosphaeria wisp, sclerosis, sclerosis, sclerosis, and so on). Erwinia sp.), Apical carcinoma (Agrobacterium tumefaciens), rust blight (Erwinia chrysanthemi pv. Chrysanthemi), and flower rot bacterial disease (Pseudomonas syringa. s ringae), bacterial wilt disease (Erwinia sp.); peach scab (Cladosporium carpophilum), homopsis rot (Phomopsis sp.), plague (Phytophthora spp.), and anthrax (Colletotrophithosporium). deformans), perforated bacterial disease (Xhanthomonas campestris pv. pruni), apical carcinoma disease (Agrobacterium tumefaciens); cherry anthracnose (Glomerella singulata), and germ fungus sclerosis (Milica koniota milion) ), Apical carcinoma (Agrobacter) um tumefaciens), resin bacterial diseases (Pseudomonas
syringae pv. syringae); oyster anthrax (Glomerella singulata); deciduous disease (Cercospora kaki; Mycosphaerella nawae); powdery mildew (Phylactinia kakikora); Green mold (Penicillium digitatum), blue mold (Penicillium italicum), scab (Elsinoe fawcettii), brown rot (Phytophthora citrophthora scab, Xhanthoma sponsamposa scab) . Yringae pv syringae), greening disease (Liberibactor asiaticus), crown gall temple petitioner disease (Agrobacterium tumefaciens);
Botrytis cinerea such as tomato, cucumber, beans, strawberries, potatoes, cabbage, eggplant, lettuce; sclerotinia sclerotium such as tomato, cucumber, beans, strawberry, potato, rapeseed, cabbage, eggplant, lettuce ); Tomato, cucumber, legumes, radish, watermelon, eggplant, rapeseed, bell pepper, spinach, sugar beet, and various other types of seedling wilt (Rhizoctonia spp., Pythium spp., Fusarium spp., Phylophthroprosa sp., Etc.) Rustonia solanacearum of Solanaceae; downy mildew of cucurbits (Pseudoperonospora cubens); s), powdery mildew (Sphaerotheca fuliginea), anthracnose (Colletotrichum orbiculare), vine blight (Didymella bryoniae), Fusarium disease (Fusarium oxysporum), plague (Phytophthora parasitica, Phytophthora melonis, Phytophthora nicotianae, Phytophthora drechsleri, Phytophthora capsici Etc.), brown spot bacterial disease (Xhanthomonas campestris pv. Cucurbitae), soft rot (Erwinia carotovora subsp. ... Gae pv lachrymans), edges bacterial grain rot (Pseudomonas marginalis pv marginalis), temple petitioner disease (Streptomyces sp), root disease (Agrobacterium rhizogenes), cucumber mosaic virus (Cucumber mosaic virus);
Tomato ring rot (Alternaria solani), leaf mold (Fulvia fulva), plague (Phytophthora infestans), wilt (Fusarium oxysporum), root rot (Pythium myriotium illum, Pythium myriotium sulcus, Pythium myriotium illum, Pythium myriotyrum, Pythium myrotylum, Pythium myriotyrum, Pythium myrotyrum, Pythium myriotium, Phytium myriotium, Pythium myriotium) Diseases (Claviobacter michiganensis), Stem Necrotic Bacterial Disease (Pseudomonas corrugata), Black Spot Bacterial Disease (Pseudomonas viridiflava), Soft Rot (Erwinia carrotova sp. ytoplasma asteris), yellow dwarf (Tobacco leaf curl subgroup III geminivirus); Brown spot bacterial disease (Pseudomonas cichorii), stem nematode bacterial disease (Pseudomonas corrugata), stem rot bacterial disease (Erwinia chrysanthemi), soft rot (Erwinia carotovora spores, spores of spores, spores, spores, spores, spores, spores and germs). Black rot (Alternaria brassicae), black rot (Xhanthomonas campestris pv. Campestris), black rot (Pseudomonas syringae pv. Eravia kuroa eroa var. Etc.), white spot disease (Cercosporella brassicae), root rot disease (Pharma lingam), clubroot disease (Plasmodiophora brassicae), downy mildew (Peronospora sarcoma, black rot sampa sampa samposa, black rot) Pseudomonas sy ringae pv. maculicola), soft rot (Erwinia carotovora subsp. carotovora);
Cabbage plant rot (Thanatephorus cucumeris), yellow rot (Fusarium oxysporum), black scab (Alternaria brassicicola); Chinese cabbage rot (Rhizotnia sulnia erutia succinata) ), Black leaf spot (Alternaria porri), white silk spot (Sclerotium rolfsii), white plague (Phytophthora porri), black rot fungus (Sclerotium sepivorum); Carot vora), spot bacterial disease (Pseudomonas syringae pv. syringae), rot (Erwinia rhapontici), scale rot (Burkholderia gladioli rot), yellow rot (Phytoplasa saunia rot) Disease (Pseudomonas marginalis pv. Marginalis); soybean purpura (Cercospora kikuchii), black rot (Elsinoe glycines), black spot (Diaporthe phasoolz, rhizopha spores and lysophia rotoh rotoh rotonia sarcopodium) e), downy mildew (Peronospora manshurica), rust (Phakopsora pachyrhizi), anthrax (Colletotrichum truncatum, etc.), leaf blight (Xanthomonas camps pesgos pest. Anthrax (Colletotrichum lindemutianum), bacterial wilt (Ralstonia solanacearum), scab (Pseudomonas syringae pv. Phaseolicola), brown spot bacterial disease (Pseudomonas visamrais virions virion virion virion virion sv. . phaseoli);
Peanut black spot (Mycosphaerella berkeleyi), brown spot (Mycosphaerella arachidis), wilt (Ralstonia solanacearum); syringae pv. pisi), vine rot (Xhanthomonas campestris pv. pisi; broad bean downy mildew (Peronospora viciae), plague (Phytophthora nicotaiana, and Phytophthora niacoa sickness). Plague (Phyto phthora infestans, silver blight (Helminthosporium solani), dry rot (Fusarium oxysporum, Fusarium solani), powdery scab (Spongospora sarva sarva sarva sarona sarva sarona sarva sarva sarona sarva sarona sarva sarva sarva sarva sarcoa).
atroseptica, Streptomyces scabies, Streptomyces acidiscabies, soft rot (Erwinia carotovora subsp. Streptomyces ipomoeae; brown spot of sugar beet (Cercospora beticola), downy mildew (Peronospora schachtiii), black root disease (Aphanomyces cochioides), and snake eye disease (Phochobium stomach disease, Phoma stomach stomach disease) . Faciens), scab (Streptomyces scabies), spot Bacterial (Pseudomonas syringae pv aptata);
Bacterial leaf blight of carrots (Alternaria dauci), club scab (Rhizobacter dauci), apical carcinoma (Agrobacterium tumefaciens), Streptomyces scab (Streptomyces spop. Strawberry powdery mildew (Sphaerotheca aphanis var. Aphanis), plague (Phytophthora nicotianae, etc.), anthrax (Glomerella singulata, etc.), fruit rot (Pythium ultimum), bacterial rot (Stium rotum), Xanthus wilt (Stithium ultarum), Xanthus wilt disease campestris), Bacterial blight (Pseudomonas marginalis pv. Marginalis); tea net rot (Exobasidium reticulatum), white scab (Elsinoe leucospila), anthrax (Colletotrichus stomach disease) syringae pv. theae, scabs (Xhanthomonas campestris pv. theicola), goblet's scab (Pseudomonas sp.); hum gloeosporioides), late blight (Phytophthora nicotianae), Wildfire Disease (Pseudomonas syringae pv.tabaci), Huang and bacterial diseases (Pseudomonas syringae pv.mellea), cavity disease (Erwinia carotovora subsp. carotovora), damping off (Ralstonia solanacearum) , Tobacco mosaic virus;
Rust of coffee (Hemileia vastatrix); Black sigatoga disease of banana (Mycosphaerella fijiensis), Panama disease (Fusarium oxysporum f. Sp cubense); Cotton wilt disease (Fusaria moria, R. sarcoa) Sclerotinia sclerotiorum, Xanthomonas campestris pv. Malvacearum, Scab disease (Erwinia carotovora subsp. Fusarium sickness (Sphaerotheca pannosa, etc.), plague (Phytophthora megasperma), downy mildew (Peronospora sparsa), root carcinoma (Agrobacterium tumefaciens), chrysanthemum spore spore spore spore spore spore spore spore spore spore spore spore spore spore spore spore spore sb. ), Plague (Phytophthora actorum), spot bacterial disease (Pseudomonas ichorii), soft rot (Erwinia carotovora subsp. ifolia); turf brown patch disease (Rhizoctonia solani), dollar spot disease (Sclerotinia homoeocarpa), curvularia leaf blight (Curvularia sp.), rust (Puccinia zoysia sp. , Scallops (Rynchosporium secalis), wilt (Gaeumannomyces graminis), anthrax (Colletotrichum sp.), Snow rot brown sclerotia (Typhula incarnata), snow rot black sclerophyll sari shirahi shira shira shira shira shira shira shira shira shira shira shira shira shira shikotsuka Bacterial bacterial rot (Myrioscleroticia borealis), fairy ring disease Marasmius Oreades etc.), Pythium disease (Pythium aphanidermatum, etc.), blast (Pyricularia grisea), and the like.

  The compound of the present invention may be used alone, but preferably is mixed with a solid carrier, liquid carrier, gas carrier, surfactant, fixing agent, dispersant, stabilizer, etc. It can be used as a composition such as water dispersible granules, aqueous solvents, aqueous granule solvents, granules, emulsions, liquids, microemulsions, aqueous suspensions, aqueous emulsions, and suspoemulsions. The composition is not limited as long as the effect is exhibited.

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

[Formulation Example 1 Flowable]
Compound of the present invention (10 parts by mass), sodium salt of formaldehyde condensate of naphthalenesulfonic acid (5 parts by mass), polyoxyethylene arylphenyl ether (1 part by mass), propylene glycol (5 parts by mass), silicon-based antifoaming agent ( 0.1 parts by mass), xanthan gum (0.2 parts by mass), ion-exchanged water (78.7 parts by mass) to form a slurry, and further wet milling using glass beads having a diameter of 1.0 mm with Dynomill KDL. To 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 with the solution 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), dioctyl sulfosuccinate sodium salt (0.5 parts by mass), alkylbenzenesulfonic acid sodium salt (5 parts by mass), calcining Diatomaceous earth (10 parts by mass) and kaolinite clay (62.5 parts by mass) are sufficiently mixed and pulverized with an air mill to obtain a wettable powder.

  Hereinafter, the application of the composition of the present invention (a pesticide for agricultural and horticultural use, a fungicide for agricultural and horticultural use) will be described.

  Examples of a method for applying the composition containing the compound of the present invention include a method in which the composition is brought into contact with a plant or a seed, and a method in which the composition is contained in a cultivated soil and brought into contact with a root or a rhizome of a plant. As specific examples, foliage spraying treatment, injection treatment, seedling box treatment, cell tray treatment, spraying treatment on plant seeds, spray treatment on plant seeds, immersion treatment on plant seeds, immersion treatment on plant seeds on plant seeds of the composition Dressing, spraying on the soil surface, soil mixing after spraying on the soil surface, injection into the soil, soil mixing after injection in the soil, soil irrigation, after soil irrigation Soil mixing and the like. In general, any method of application as used by those skilled in the art will work well.

  The term "plant" as used in the present invention refers to a plant that performs photosynthesis and lives without exercise. Specific examples include rice, wheat, barley, corn, coffee, banana, grape, apple, pear, peach, cherry, oyster, citrus, soybean, bean, cotton, strawberry, potato, cabbage, lettuce, tomato, cucumber, eggplant, Watermelon, sugar beet, spinach, snow pea, pumpkin, sugar cane, tobacco, bell pepper, sweet potato, taro, konjac, cotton, sunflower, rose, tulip, chrysanthemum, turf, etc. and their F1 varieties and the like can be mentioned. In addition, it includes genetically modified crops that are produced by manipulating genes and the like and are not originally present in the natural world.For example, soybeans, corn, cotton, etc. that have been imparted with herbicide resistance, such as rice adapted to cold regions. And agricultural and horticultural crops, such as corn and cotton, to which insecticide-producing ability is imparted. Further, trees such as pine, ash, ginkgo, maple, oak, poplar, zelkova and the like can be mentioned. The “plant” in the present invention is a general term for all parts constituting the above-mentioned plant individual, and includes, for example, stems, leaves, roots, seeds, flowers, fruits and the like.

  The “seed” as used in the present invention refers to a seed that stores nutrients for germinating young plants and is used for agricultural reproduction. Specific examples include seeds of corn, soybeans, cotton, rice, sugar beet, wheat, barley, sunflower, tomato, cucumber, eggplant, spinach, snow peas, pumpkin, sugar cane, tobacco, peppers, oilseed rape, and their F1 varieties. Examples include seeds, seed potatoes such as taro, potato, sweet potato, and konjac, edible lilies, bulbs such as tulips, seed balls such as rakkyo, and seeds and tubers of genetically modified crops.

  The application rate and application concentration of the composition containing the compound of the present invention vary depending on the target crop, the target disease, the degree of occurrence of the disease, the dosage form of the compound, the application method, and various environmental conditions. The amount of the active ingredient is suitably from 0.1 to 10,000 g per hectare, preferably from 10 to 1,000 g per hectare. The amount used in the case of seed treatment is 0.0001 to 1000 g, preferably 0.001 to 100 g, per kg of seed as an active ingredient. When the composition containing the compound of the present invention is used as a foliage spraying treatment on a plant individual, a spraying treatment on a soil surface, an injection treatment into soil or a soil irrigation treatment, the composition is diluted with an appropriate carrier at an appropriate concentration. Thereafter, the processing may be performed. When the composition containing the compound of the present invention is brought into contact with a plant seed, it may be diluted to an appropriate concentration and then immersed, dressed, sprayed or smeared on the plant seed before use. 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 dried plant seeds as an active ingredient. Is appropriate, but 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 composition containing the compound of the present invention may contain, if necessary, other pesticides, such as fungicides, pesticides, acaricides, nematicides, herbicides, pesticides such as biological pesticides and plant growth regulators, nucleic acids. Can be used in admixture with a disease control agent (WO 2014/062775), a soil conditioner or a fertilizer which contains as an active ingredient. . As a method of mixing and using the compound of the present invention and another pesticide, a method of formulating and using the compound of the present invention and another pesticide in one dosage form, and both methods in which each is formulated in a separate dosage form Are used before and after use, or both are separately formulated in separate dosage forms, or both are formulated in separate dosage forms. And then use the other.

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

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

b-2: Mitotic and mitosis inhibitor [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] Dietofencarb, [b-2,8] zoxamide, [b-2.9] ethaboxam, [b-2.10] pencyclocurn, [b-2. 11] Fluopico Lido (fluopicolide), [b-2.12] phenamacril, and the like.

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

b-4: quinone external inhibitor (QoI agent)
[B-4.1] azoxystrobin, [b-4.2] cumoxystrobin, [b-4.3] dimoxyst as quinone external inhibitors (QoI agents) Robin (dimoxystrobin), [b-4.4] enoxastrobin, [b-4.5] famoxadone, [b-4.6] fenamidone, [b-4.7] ] Phenaminestrobin, [b-4.8] fluenoxystrobin, [b-4.9] fluoxastrobin, [b-4.10] kresoxim-methyl hyl), [b-4.11] Mandestrobin, [b-4.12] Metominostrobin, [b-4.13] Orysastrobin, [b-4.14] Picoxystrobin, [b-4.15] pyraclostrobin, [b-4.16] pyramethostrobin, [b-4.17] pyraoxystrobin , [B-4.18] pyribencarb, [b-4.19] triclopyricarb, [b-4.20] trifloxystrobin (trifloxyst) obin), and the like.

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

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

b-7: quinone external stigmatelin binding subsite inhibitor (QoSI agent)
Examples of the quinone external stigmatelin binding subsite inhibitor (QoSI agent) include [b-7.1] amethoctrazine.

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

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

b-10: Signaling inhibitor As a signalling inhibitor, [b-10.1] fenpiclonil, [b-10.2] fludioxonil, [b-10.3] quinoxyfen, [B-10.4] proquinazide, [b-10.5] clozolinate, [b-10.6] dimethaclone, [b-10.7] iprodione, [b -10.8] procymidone, [b-10.9] vinclozolin and the like.

b-11: Lipid and cell membrane biosynthesis inhibitor [b-11. 1] edifenphos, [b-11.2] iprobenphos, [b-11.3] as lipid and cell membrane biosynthesis inhibitors. Pyrazophos, [b-11.4] isoprothiolane, [b-11.5] biphenyl, [b-11.6] chloroneb, [b-11.7] dichlorane (Dicloran), [b-11.8] quintogene, [b-11.9] technazen, [b-11.10] tolclofos-methyl, [b-11.11] Etridiazole (ec hlemozol 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. [b-12.4] cyproconazole, [b-12.5] difenoconazole, [b-12.6] diconizazole, [b-12.7] diconizazole-M ), [B-12.8] epoxiconazole, [b-12.9] etaconazole, [b-12.10] fenarimol, [b-12.11] 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] microbutanil , [B-12.22] nuarimol, [b-12.23] oxpoconazole, [b-12.24] oxpoconazole fumarate, [b- 12.25] pefurazoate, [b-12.26] 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 fungicide [b-13.1] aldimorph, [b-13.2] dodemorph, [b-13.3] fenpropimorph as an amine fungicide ), [B-13.4] tridemorph, [b-13.5] fenpropidin, [b-13.6] piperaline, [b-13.7] spiroxamine ) And the like.

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

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

b-16: Cell wall biosynthesis inhibitor As a cell wall biosynthesis inhibitor, [b-16.1] polyoxins (polyoxins), [b-16.2] dimethomorph, [b-16.3] flumorph ( flumorph), [b-16.4] pyrimorph, [b-16.5] benthiavalicarb, [b-16.6] bentivaricarb-isopropyl, [b -16.7] iprovalicarb, [b-16.8] mandipropamide, [b-17.9] varifenalate, and the like.

b-17: Melanin biosynthesis inhibitor As a melanin biosynthesis inhibitor, [b-17.1] fthalide or phthalide, [b-17.2] pyroquilone, and [b-17.3] tricyclazole. (Triclazole), [b-17.4] carpropamide, [b-17.5] diclocymet, [b-17.6] phenoxanil, [b-17.7] tolprocarb (tolprocarb) ) And the like.

b-18: Host plant resistance inducer [b-18.1] acibenzolar-S-methyl, [b-18.2] probenazole, [b-18.1] acibenzolar-S-methyl, as a host plant resistance inducer -18.3] thiadinil, [b-18.4] isotianil, [b-18.5] laminarin, and the like.

b-19: Dithiocarbamate fungicide [b-19.1] Mancozeb or manzeb (mancozeb or manzeb), [b-19.2] Manneb (maneb), [b-19.3] as a dithiocarbamate fungicide ] Methiram, [b-19.4] propineb (propineb), [b-19.5] thiuram (thiram), [b-19.6] zineb, [b-19.7] ziram (Ziram), [b-19.8] ferbam and the like.

b-20: Phthalimide-based disinfectant As a phthalimide-based disinfectant, [b-20.1] captan, [b-20.2] captafol, [b-20.3] folpet (folpet) ), [B-20.4] fluorophorpet and the like.

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

b-22: Multi-acting point contact active fungicide [b-22.1] Basic copper chloride (copper oxychloride), [b-22.2] Cupric hydroxide as multi-acting point contact active fungicide (Copper (II) hydroxide), [b-22.3] basic copper sulfate, [b-22.4] organic copper compound (organocopper compound), [b-22.5] dodecylbenzene sulfone Acid bisethylenediamine copper complex [II] (Dodecylbenzenesulphonic acid bisethylenediamine copper [II] salt, DBEDC), [b-22.6] sulfur, [b-22.7] fluoroimide (fluorim) de), [b-22.8] chlorothalonil, [b-22.9] dichlofluanid, [b-22.10] tolylfluanid, [b-22.11] Anilazine, [b-22.12] dithianon, [b-22.13] quinomethionate or quinomethionate, [b-22.14] Extract from cotyledon of birch seedling (BLAD), etc. Is mentioned.

b-23: Other fungicides As other fungicides, [b-23.1] dichlobentiazox, [b-23.2] fenpicoxamide, [b-23.3]. ] Dipymetitron, [b-23.4] bupirimate, [b-23.5] dimethylimol, [b-23.6] ethirimol, [b-23.7] acetic acid Triphenyltin (fentin acetate), [b-23.8] triphenyltin chloride (fentin chloride), [b-23.9] triphenyltin hydroxide (fentin hydroxide), [b-23.10] oxolinic acid (Oxo linic acid), [b-23.11] hymexazole, [b-23.12] octilinone, [b-23.13] fosetyl, [b-23.14] phosphorous acid (Phosphorous acid), [b-23.15] sodium phosphite (sodium phosphite), [b-23.16] ammonium salt of phosphite (ammonia phosphite), [b-23.17] phosphorus phosphite Potassium salt of acid (potassium phosphate), [b-23.18] teclophthalam, [b-23.19] triazoxide, [b-23.20] flusulfamide [B-23.21] diclomezine, [b-23.22] silthiofam, [b-23.23] diflumetorim, [b-23.24] metasulfocarb, [B-23.25] cyflufenamide, [b-23.26] metrafenone, [b-23.27] pyriophenone, [b-23.28] dodine, [b] -23.29] flutianil, [b-23.30] ferimzone, [b-23.31] oxathiapiprolin, [b-23. 32] tebufloquine, [b-23.33] picarbutrazox, [b-23.34] validamycins, [b-23.35] simoxanil, [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] Equation (s1)

(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] Equation (s2)

(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)

(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] Equation (s4)

A compound represented by the following formula (see International Publication No. 12/084812):

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

A compound (gougerotin) represented by

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

A compound (ningnanmycin) represented by:

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

(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] Equation (s8)

(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] Equation (s9)

(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] Equation (s10)

(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] Equation (s11)

(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] Equation (s12)

(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] Equation (s13)

(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] Equation (s14)

(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)

(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] Equation (s16)

[Wherein, A3 represents a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a cyano group, and A4 represents a hydrogen atom, a C1-C6 alkyl group, a C1-C6 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] Equation (s17)

[In the formula, m1 represents an integer of 0 to 3, A5 and A6 each independently represent a halogen atom or a C1 to C6 alkyl group, A7 and A8 each independently represent, Represents a halogen atom or a C1 to C6 alkoxy group, and when m1 is 2 or more, two or more A7s each represent an independent substituent, which may be the same or different. (See WO09 / 137538 and WO09 / 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] Equation (s18)

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

［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] Equation (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 to C6 alkyl group, and A16 represents a hydrogen atom, a halogen atom. Or C1 to C6 alkoxy group, A17 represents a halogen atom or a C1 to C6 alkoxy group, and when m2 is 2 or more, two or more A17 each represent an independent substituent, and May 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] Equation (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 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] Equation (s21)

[Wherein, 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 WO 07/087906, WO 09/016220, WO 10/130767),

［式中、ｍ３は、０〜５の整数を表し、Ａ２５は、ハロゲン原子、Ｃ１〜Ｃ６のアルキル基、Ｃ１〜Ｃ６のハロアルキル基、Ｃ１〜Ｃ６のアルコキシ基、Ｃ１〜Ｃ６のハロアルコキシ基、またはＣ３〜Ｃ８のシクロアルキル基を表し、ｍ３が２以上の場合、２以上のＡ２５は、それぞれ独立した置換基を表し、同一または異なっていてよい。］で表される化合物（国際公開第１３／０９２２２４号参照）、[B-23.58] Equation (s22)

[Wherein, m3 represents an integer of 0 to 5, A25 represents 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 when it represents a C3-C8 cycloalkyl group and m3 is 2 or more, two or more A25s each represent an independent substituent and may be the same or different. (See WO 13/092224),

［式中、Ａ２６は、水素原子、またはハロゲン原子を表し、Ｖ１およびＶ２は、それぞれ独立していて、酸素原子、または硫黄原子を表す。］で表される化合物（国際公開第１２／０２５４５０号参照）、[B-23.59] Equation (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] Equation (s24) or Equation (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. And when m4 is 2 or more, two or more A28s each represent an independent substituent and may be the same or different, and A29 is a C1-C6 alkyl group, a C2-C6 alkenyl group, or a C3 Represents an alkynyl group of -C6. ] (See WO 13/037771),

［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] Equation (s26) or Equation (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. And when m5 is 2 or more, two or more A31s each represent an independent substituent and may be the same or different, and A32 is a C1-C6 alkyl group, a C2-C6 alkenyl group, or a C3 Represents an alkynyl group of -C6. ] (See WO 13/037771),

［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] Equation (s28)

[Wherein A33, A34, A35 and A36 are each independently a hydrogen atom or a halogen atom, and A37 represents a hydrogen atom, an acetyl group or a benzoyl group. (See WO 06/031631, WO 10/069882),

［式中、Ａ３８は、Ｃ１〜Ｃ６のアルキル基、またはＣ１〜Ｃ６のハロアルキル基を表し、Ａ３９およびＡ４０は、それぞれ独立していて、水素原子、またはハロゲン原子を表す。］で表される化合物（国際公開第１４／０４３３７６号参照）、[B-23.63] Equation (s29)

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

［式中、Ａ４１は、水素原子、水硫基（−ＳＨ）、チオシアン酸基（−ＳＣＮ）、またはＣ１〜Ｃ６のアルキルチオ基を表し、Ａ４２、Ａ４３、Ａ４４およびＡ４５は、それぞれ独立していて、水素原子、またはハロゲン原子を表す。］で表される化合物（国際公開第０９／０７７４４３号参照）、[B-23.64] Formula (s30)

[Wherein, A41 represents a hydrogen atom, a hydroxyl group (-SH), a thiocyanate group (-SCN), or an alkylthio group of C1 to C6, 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-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)

[Wherein, A49, A50 and A51 each independently represent a hydrogen atom or a halogen atom. (See International Publication No. 11/081174).

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

Group c:
c-1: Carbamate acetylcholinesterase (AChE) inhibitor As a carbamate acetylcholinesterase (AChE) inhibitor, [c-1.1] phosphocarb, [c-1.2] alanicarb, [c] -1.3] butoxycarboxym, [c-1.4] butoxycarboxym, [c-1.5] thiodicarb, [c-1.6] thiofanox. ), [C-1.7] aldicarb, [c-1.8] bendiocarb, [c-1.9] benfuracarb, [c-1.10] carbaryl ryl), [c-1.11] carbofuran, [c-1.12] carbosulfan, [c-1.13] ethiofencarb, [c-1.14] fenobcarb ( fenobucarb, [c-1.15] formetanate, [c-1.16] furathiocarb, [c-1.17] isoprocarb, [c-1.18] methiocarb. , [C-1.19] methomyl, [c-1.20] oxamyl, [c-1.21] pirimicarb, [c-1.22] propoxur, c-1.23] trimetacarb, [c-1.24] XMC (3,5-xylylmethylcarbamate), [c-1.25] alixycarb, [c-1.25] aldoxycarb (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 bendiocarb), and the like.

c-2: Organophosphorus acetylcholinesterase (AChE) inhibitor As the organophosphorus acetylcholinesterase (AChE) inhibitor, [c-2.1] acephate, [c-2.2] azamethiphos, [C-2.3] Azinphos-methyl, [c-2.4] Azinphos-ethyl, [c-2.5] Ethephon, [c-2.6] ] Cadusafos, [c-2.7] chloroethoxyphos, [c-2.8] chlorfenvinphos, [c-2.9] chlormephos, [c- 2.10] black Lupyrifos (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] disul Disulfonton, [c-2.22] O-ethyl O-4-nitrophenyl phenylphosphonothioate (O-ethyl O-4-nitrophenyl phenylphosphonothioate), [c-2.23] ethion, [ [c-2.24] etoprophos, [c-2.25] famfur, [c-2.26] fenamiphos, [c-2.27] fenitrothion, [c- 2.28] fenthion, [c-2.29] fosthiazate, [c-2.30] heptenophos, [c-2.31] isofenphos-methyl isofenphos-methyl, [c-2.32] isocarbobophos, [c-2.33] isoxathion, [c-2.34] malathion, [c-2.35] mecarbam ( mecarbam), [c-2.36] methamidophos, [c-2.37] methidathion, [c-2.38] mevinphos, [c-2.39] monocrotophos ), [C-2.40] nared, [c-2.41] omethoate, [c-2.42] oxydemethon-methyl, [c-2.4] ] Parathions, [c-2.44] parathion-methyl, [c-2.45] phenthoate, [c-2.46] phorate, [c-2] .47] phosphorone, [c-2.48] phosmet, [c-2.49] phosphamidon, [c-2.50] phoxim, [c-2.51]. ] Pirimiphos-methyl, [c-2.52] propenofos, [c-2.53] propetamphos, [c-2.54] prothiophos, [c-2] .55] Pyraclofos, [c-2.56] pyridaphenthion, [c-2.57] quinalphos, [c-2.58] sulfotep, [c-2.59] tebupyrimphos ( tebupirimfos), [c-2.60] temephos, [c-2.61] terbufos, [c-2.62] thiometon, [c-2.63] triazophos. , [C-2.64] trichlorfon, [c-2.65] vamidothion, [c-2.66] chlorthion, [c-2.67] bromophene Bromfenvinfos, [c-2.68] bromophos, [c-2.69] bromophos-ethyl, [c-2.70] butathiophos, [c-2. 71] carbofenothion, [c-2.72] chlorphoxim, [c-2.73] sulprofos, [c-2.74] diamidafos, [c-2. 75] tetrachlorvinphos, [c-2.76] propaphos, [c-2.77] mesulfenphos, [c-2.78] dioxabenzo (Dioxabenzofos), [c-2.79] etrimfos, [c-2.80] oxydeprofos, [c-2.81] formothion, [c-2.82] Fensulfothion, [c-2.83] isazofos, [c-2.84] imiciafos, [c-2.85] isamidofos, [c-2.86] thionazine ( thionazin), [c-2.87] fosthiethane, and the like.

c-3: GABA-operated chloride ion channel blocker [c-3.1] chlordane, [c-3.2] endosulfan, [c-3.3] as GABA-operated chloride ion channel blockers. ] Lindane, [c-3.4] dienochlor, [c-3.5] ethiprole, [c-3.6] fipronil, [c-3.7] aceto Aceproprole and the like.

c-4: Sodium channel modulator As a sodium channel modulator, [c-4.1] acrinathrin, [c-4.2] arethrin [(1R) -isomer] (allethrin [(1R) -isomer]), [C-4.3] bifenthrin, [c-4.4] bioallethrin, [c-4.5] bioallethrin S-cyclopentenyl isomer (bioallthrin S-cyclopentenyl isomer), [c- 4.6] bioresmethrin, [c-4.7] cycloprothrin, [c-4.8] cyfluthrin, [c-4. Beta-cyfluthrin, [c-4.10] cyhalothrin, [c-4.11] gamma-cyhalothrin, [c-4.12] lambda-cyhalothrin (lambda) -Cyhalothrin, [c-4.13] cypermethrin, [c-4.14] alpha-cypermethrin, [c-4.15] beta-cypermethrin , [C-4.16] cet-cypermethrin, [c-4.17] zeda-cypermethrin, [c-4.18] cypheno Trin [(1R) -trans-isomer] (cyphenothrin [(1R) -trans-isomer]), [c-4.19] deltamethrin, [c-4.20] empentrin [(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] flucitrinate, [c-4.26] flumethrin , [C-4.27] tau-fluvalinate, [c-4.28] halfenprox, [c-4.29] imiprothrin, [c-4.30] Methothrin, [c-4.31] Methofluthrin, [c-4.32] Epsilon-methfluthrin, [c-4.33] Monfluorothrin, [c] -4.34] epsilon-momofluorothrin, [c-4.35] permethrin, [c-4.36] phenothrin [(1R) -trans-A] Sommer] (phenothrin [(1R) -trans-isomer]), [c-4.37] praletrin, [c-4.38] resmethrin, [c-4.39] cadetrin , [C-4.40] silafluofen, [c-4.41] tefluthrin, [c-4.42] tetramethrin, [c-4.43] tetramethrin [(1R)- Isomers] (tetramethrin [(1R) -isomer]), [c-4.44] tralomethrin, [c-4.45] transfluthrin, [c-4.46] ZXI8 901 (3- (4-bromophenoxy) phenyl] -cyanomethyl4- (difluoromethoxy) -α- (1-methylethyl) benzoeneacetate, [c-4.47] Biopermethrin (biopermethrin), [c-4. furamethrin, [c-4.49] profluthrin, [c-4.50] flubrocytrinate, [c-4.51] dimfluthrin, [c-4.52] DDT (Dichloro-diphenyl-trichloroethane), [c-4.53] methoxychlor, [c-4. 4] phenothrin (phenothrin), and the like [c-4.55] fluvalinate (fluvalinate).

c-5: Nicotinic acetylcholine receptor (nAChR) competitive modulator As a nicotinic acetylcholine receptor (nAChR) competitive modulator, [c-5.1] acetamiprid (acetamiprid), [c-5.2] clothianidin (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] sulphate Kisafuroru (sulfoxaflor), [c-5.11] Furupirajifuron (flupyradifurone), and the like [c-5.12] triflupromazine meso pyridinium beam (triflumezopyrim).

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

c-7: Glutamate-operated chloride channel (GluCl) allosteric modulator [c-7.1] abamectin, [c-7.2] emamectin benzoate as a glutamate-operated chloride channel (GluCl) allosteric modulator Salt (emmectin 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] quinoprene (kinoprene), [c-8.3] methoprene (methoprene) ), [C-8.4] phenoxycarb, [c-8.5] pyriproxyfen, and the like.

c-9: Non-specific (multi-site) inhibitor As a non-specific (multi-site) inhibitor, [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] borane Acid (boric acid), [c-9.7] disodium octaborate, [c-9.8] sodium metaborate [c-9.9] tartar emetic), [c-9.10] dazomet, [c-9.11] metham (m etam), [c-9.12] carbam sodium salt and the like.

c-10: String Organ TRPV Channel Modulator Examples of the string organ TRPV channel modulator include [c-10.1] pymetrozine, [c-10.2] pyrifluquinazone, and the like.

c-11: Mite growth inhibitor As a mite growth inhibitor, [c-11. 1] clofentezine, [c-11. 2] diflobidazine, [c- 11.3] hexithizox. (Hexythiazox), [c-11.4] ethoxazole, 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] chlorfenapyr, [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 a nicotinic acetylcholine receptor (nAChR) channel blocker, [c-14.1] bensultap, [c-14.2] cartap hydrochloride (cartap) hydrochloride), [c-14.3] thiocyclam, [c-14.4] monosultap, and the like.

c-15: chitin biosynthesis inhibitor type 0
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] Rifurumuron (triflumuron), and the like.

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

c-17: Inhibitor of moltid insect molting Examples of the insect moulting inhibitor of Diptera include [c-17.1] cyromazine.

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

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

c-20: Mitochondrial electron transport complex III inhibitor [c-20.1] hydramethylnon, [c-20.2] acequinocyl, as a mitochondrial electron transport complex III inhibitor [C-20.3] fluacryliprim, [c-20.4] bifenazate, and the like.

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

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

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

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

c-25: mitochondrial electron transport system complex II inhibitor [c-25.1] cyenopyrafen, [c-25.2] cyflumetofen, [c-25.1] cyenopyrafen -25.3] piflubumide and the like.

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

c-27: String Organ Modulator with Unspecified Target Site The string organ modulator with unspecified target site includes [c-27.1] flonicamid.

c-28: Other insecticides As other insecticides, [c-28.1] azadirachtin, [c-28.2] benzoximate (benzoximate), [c-28.3] phenisobromo Phenisobromolate, [c-28.4] quinomethionate, [c-28.5] dicofol, [c-28.6] pyridalyl, [c-28.7] bromopropiate Rate (bropropylate), [c-28.8] triazamate, [c-28.9] dicyclanil, [c-28.10] dinobuton, [c-28.11] dinocup ( din ocap), [c-28.12] hydrogen cyanide, [c-28.13] methyliodide, [c-28.14] Karanjin, [c-28.15] chloride 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 salt (sulcofuron-sodium), [c-28.23] tribubufos, [c-28.24] aldrin, [c-28.25]. Amidithione, [c-28.26] amidothioate, [c-28.27] aminocarb, [c-28.28] amiton, [c-28.29] Aramite, [c-28.30] athidathion, [c-28.31] azotoate, [c-28.32] polysulfide barium (barium polysulfide), [c-2] 8.33] venclothiaz, [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-ethyethanol, [c-28.36] butonate, [c-28.37] butopyronoxyl, [c-28.38] 2- (2-butoxyethoxy) ethyl thiocyanate (2- ( 2-butyethoxy) ethyl thiocyan te), [c-28.39] camphechlor, [c-28.40] chlorbenside, [c-28.41] chlordecone, [c-28.42] chlordiforme , [C-28.43] chlorphenetol, [c-28.44] chlorfenson, [c-28.45] fluazuron, [c-28.46] methaldehyde (Metaldehyde), [c-28.47] bialaphos, [c-28.48] levamisole hydrochloride (levamisol), [c-28.49] amidoflumet , [C-28.50] pyrafluprole, [c-28.51] pyriprole, [c-28.52] tralopyryl, [c-28.53] flupyrazofos , [C-28.54] diophenolan, [c-28.55] chlorobenzilate, [c-28.56] flufenzine, [c-28.57] benzomate , [C-28.58] flufenerim, [c-28.59] albendazole, [c-28.60] oxybendazole. [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] tetranyliprole, [c-28.67] brofuranilide (Broflanilide), [c-28.68] dichloromezzotiaz, [c-28.69] ethylene dibromide, [c-28.70] acrylonitrile ( (cryonitrile), [c-28.71] bis (2-chloroethyl) ether, [c-28.72] 1-bromo-2-chloroethane (1-bromo-2-chloroethane) , [C-28.73] 3-bromo-1-chloroprop-1-ene, [c-28.74] bromocyclen, [c-28. 75] carbon disulfide, [c-28.76] carbon tetrachloride (tetrachlormethane), [c-28.77] nemadectin, [c-28.78] cymizazole [c- 28.79] Cal Um polysulfide (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] anabacine ( anabasine), [c-28.87] morantel tartrate, [c-28.88] pyrethrin (pyrethrum), [c-28.89] rapeseed oil, [c- 28.90 Soybean lecithin, [c-28.91] starch, [c-28.92] hydroxypropyl starch, [c-28.93] fatty acid glyceride (decanoylcanoylglycerol-28). 94] Propylene glycol monofatty acid ester, [c-28.95] diatomite, [c-28.96] afoxolaner, [c-28.97] Full azaind Lysine (fluazaindolizine), [c-28.98] affidopyropen, [c-28.99] Rhosylamide (cyhalodiamide), [c-28.100] thioxazafen, [c-28.101] Fluhexafon, [c-28.102] Flularaner, [c-28.103] Fluxametamide, [c-28.104] tetrachlorantraniliprole, [c-28.105] saloraner, [c-28.106] lotilaner, [c-28] .107] cycloxaprid, [c-28.108] fluensulfone, [c-28.109] TPIC ( ripropyl 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-dicarboxymide), [ c-28.1 6] Bayer 22408 (O, O-diethyl O-naphthalimidophosphorothioate), [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] Equation (s34)

(See WO10 / 051926),

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

(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] Equation (s36)

A compound represented by the formula (see International Publication No. 12/029672):

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

(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] Equation (s38)

(See WO 14/053450, WO 15/144683);

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

(See WO 14/053450, WO 15/144683);

で表される化合物（国際公開第１４／０５３４５０号、国際特許第１５／１４４６８３号参照）、[C-28.124] Equation (s40)

(See WO 14/053450, WO 15/144683);

［式中、ｍ６は、０〜２の整数を表す。］で表される化合物（国際公開第１０／１２９４９７号参照）、[C-28.125] Equation (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] Equation (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] Equation (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] Equation (s44)

[Wherein, A52 represents a hydrogen atom or a fluorine atom. (See WO 11/134964, WO 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] Equation (s45)

[Wherein, 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] Equation (s46)

[Wherein, V3 represents a nitrogen atom, a carbon atom, or C-F, 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)

[Wherein, 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 WO09 / 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;

Represents one kind of partial structure selected from the group consisting of: (See International Publication No. 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] Equation (s49)

[Wherein, A59 represents a hydrogen atom, a fluorine atom, or a chlorine atom;

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] Equation (s51)

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

Represents a partial structure selected from the group consisting of (See WO 15/038503, WO 16/144351, WO 16/144678),

［式中、Ａ６５は、水素原子、Ｃ１〜Ｃ６のアルキル基、またはＣ１〜Ｃ６のハロアルキル基を表し、Ａ６６は、水素原子、ハロゲン原子、またはＣ１〜Ｃ６のアルキル基を表し、Ａ６７およびＡ６８は、それぞれ独立していて、水素原子、シアノ基で適宜置換されてもよいＣ１〜Ｃ６のアルキル基、メトキシ基で適宜置換されてもよいアルキル基、エトキシ基で適宜置換されてもよいアルキル基、またはＣ３〜Ｃ８のシクロアルキル基を表し、Ａ６９は、水素原子、シアノ基、シアノ基で適宜置換されてもよいＣ１〜Ｃ６のハロアルキル基、Ｃ１〜Ｃ６のアルキル基、またはＣ３〜Ｃ８のシクロアルキル基を表す。］で表される化合物（国際公開第１２／１４３３１７号、国際特許第１６／０１６３６９号参照）、[C-28.136] Equation (s52)

[Wherein, 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 represent A hydrogen atom, a C1-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 a C3 to C8 cycloalkyl group, and A69 represents a hydrogen atom, a cyano group, a C1 to C6 haloalkyl group optionally substituted with a cyano group, a C1 to C6 alkyl group, or a C3 to C8 cycloalkyl group. Represents a group. (See WO 12/143317, WO 16/016369),

［式中、Ａ７０は、メチル基、エチル基、イソプロピル基、２，２，２−トリフルオロエチル基、またはフェニル基を表し、Ａ７１は、

からなる群から選択される部分構造を表し、Ａ７２は、

からなる群から選択される部分構造を表し、Ｖ８は、酸素原子、硫黄原子、−ＣＨ_２−、または−ＣＨ_２ＣＨ_２−を表す。］で表される化合物（国際公開第１４／１６７０８４号、国際特許第１６／０５５４３１号参照）、[C-28.137] Equation (s53) or Equation (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 - represents a. (See International Publication No. 14/167084, International Patent Publication 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] Equation (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, 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. A compound represented by the formula (see International Patent Publication No.

［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] Equation (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] asynonapyr,
[C-28.142] Equation (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, and A94 and A95 are each independently a hydrogen atom, a C1-C6 alkyl group, Or a C1 to C6 haloalkyl group. And the like (see WO 12/1664698).

  The mixing ratio of the compound of the present invention and the pesticide is not particularly limited as long as the effect is exhibited. It is a ratio of 1,000, preferably a ratio of 0.01 to 100.

  Hereinafter, the present invention will be described in more detail with reference to Synthesis Examples, Reference Examples, and Test Examples, but the present invention is not limited thereto.

[Synthesis Example 1]
Step 1: Synthesis of 4- (3- (2-chlorophenyl) -6-oxo-1,4,5,6-tetrahydropyridin-2-yl) -3,5-difluorobenzonitrile

  To 361 mg of unpurified 4- (2-chlorophenyl) -5-oxo-5- (4-cyano-2,6-difluorophenyl) pentanoic acid obtained in Reference Example 1, 2.96 g of ammonium acetate and 4 ml of acetic acid were added. In addition, the mixture was stirred at 110 ° C. for 10 hours. After cooling to room temperature, water and ethyl acetate were added to the reaction mixture for liquid separation. The obtained organic layer was washed successively with a saturated aqueous solution of sodium hydrogen carbonate and a saturated saline solution, 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 108 mg of a brown solid.

¹ H-NMR (CDCl ₃ ) δ: 7.33 (1H, dd, J = 8.1, 1.2 Hz), 7.16-7.14 (2H, m), 7.09-7.03 (2H, m), 6.96-6.94 (1H, m), 6.87 (1H, s), 2.97-2.96 (1H, m), 2.83-2.80 (1H , M), 2.75-2.69 (2H, m).

Step 2: Synthesis of 4- (3- (2-chlorophenyl) -1-ethyl-6-oxo-1,4,5,6-tetrahydropyridin-2-yl) -3,5-difluorobenzonitrile (Compound No. 34)

  Contains 361 mg of 4- (3- (2-chlorophenyl) -6-oxo-1,4,5,6-tetrahydropyridin-2-yl) -3,5-difluorobenzonitrile, 70 μl of ethyl iodide and 287 mg of cesium carbonate 3 ml of the DMF solution was stirred at 50 ° C. for 3 hours. After cooling to room temperature, water and ethyl acetate were added to the reaction mixture for liquid separation. The obtained organic layer was washed successively with water, an aqueous solution of sodium thiosulfate and saturated saline, 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 114 mg of a brown oil.

[Synthesis Example 2]
Synthesis of 4- (3- (2-chlorophenyl) -1-ethyl-6-oxo-1,6-dihydropyridin-2-yl) -3,5-difluorobenzonitrile (Compound No. 35)

  4 ml of a carbon tetrachloride solution containing 102 mg of 4- (3- (2-chlorophenyl) -1-ethyl-6-oxo-1,4,5,6-tetrahydropyridin-2-yl) -3,5-difluorobenzonitrile To the mixture were added 49 mg of N-bromosuccinimide and 4.3 mg of azobisisobutyronitrile, and the mixture was stirred at 80 ° C for 1 hour. After cooling to room temperature, water and dichloromethane were added to the reaction mixture to carry out liquid separation. The obtained organic layer was washed sequentially with an aqueous solution of sodium thiosulfate and water, 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 87 mg of a white solid.

[Synthesis Example 3]
Synthesis of 4- (5-chloro-3- (2-chlorophenyl) -1-ethyl-6-oxo-1,6-dihydropyridin-2-yl) -3,5-difluorobenzonitrile (Compound No. 36)

  27 mg of N-chlorosuccinimide was added to 2 ml of a DMF solution containing 72 mg of 4- (3- (2-chlorophenyl) -1-ethyl-6-oxo-1,6-dihydropyridin-2-yl) -3,5-difluorobenzonitrile. In addition, the mixture was stirred at 60 ° C. for 1 hour. After cooling to room temperature, ethyl acetate and water were added to the reaction mixture for liquid separation. The obtained organic layer was washed sequentially with an aqueous solution of sodium thiosulfate and saturated saline, and then 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 73 mg of a white solid.

[Synthesis Example 4]
Synthesis of 5- (2-chloro-3,5-dimethoxyphenyl) -1-methyl-6- (2,6-difluoro-4- (propyn-2-yloxy) phenyl) pyridin-2 (1H) -one ( Compound No. 4)

  5- (2-chloro-3,5-dimethoxyphenyl) -1-methyl-6- (2,6-difluoro-4-hydroxyphenyl) pyridine-2 (1H) obtained in Reference Example 2 (Step 10). 4 ml of an acetonitrile solution containing 70 mg of -one, 20 µl of propargyl bromide and 84 mg of cesium carbonate was stirred at room temperature for 3 hours. A saturated aqueous ammonium chloride solution and ethyl acetate were added to the reaction mixture, and the mixture was separated. The obtained organic layer was washed with saturated saline and dried over sodium sulfate. The obtained residue was purified by silica gel column chromatography. The title compound was obtained as 72 mg of an oil.

[Synthesis Example 5]
Synthesis of 5- (2-chloro-3,5-dimethoxyphenyl) -1-methyl-6- (2,6-difluoro-4- (methoxymethoxy) phenyl) pyridin-2 (1H) -one (Compound No. 5) )

  5- (2-chloro-3,5-dimethoxyphenyl) -1-methyl-6- (2,6-difluoro-4-hydroxyphenyl) pyridine-2 (1H) obtained in Reference Example 2 (Step 10). 3 ml of a THF solution containing 65 mg of -one and 14 mg of 60% sodium hydride was stirred at room temperature for 5 minutes. Next, 18 μl of chloromethyl methyl ether was added, and the mixture was stirred at room temperature for 3 hours. A saturated aqueous ammonium chloride solution and ethyl acetate were added to the reaction mixture, and the mixture was separated. The obtained organic layer was washed with saturated saline and dried over sodium sulfate. The obtained residue was purified by silica gel column chromatography. The title compound was obtained as 72 mg of a white solid.

[Synthesis Example 6]
Synthesis of 5- (2-chloro-3,5-dimethoxyphenyl) -1-methyl-6- (2,6-difluoro-4- (methoxyethoxy) phenyl) pyridin-2 (1H) -one (Compound No. 6) )

  5- (2-chloro-3,5-dimethoxyphenyl) -1-methyl-6- (2,4,6-trifluorophenyl) pyridine-2 (1H)-obtained in Reference Example 2 (Step 8). 2 ml of a THF solution containing 80 mg of ON, 46 μ of 2-methoxyethanol and 23 mg of 60% sodium hydride was stirred at room temperature for 4 hours. A saturated aqueous ammonium chloride solution and ethyl acetate were added to the reaction mixture, and the mixture was separated. The obtained organic layer was washed with saturated saline and dried over sodium sulfate. The obtained residue was purified by silica gel column chromatography. The title compound was obtained as 75 mg of an amorphous solid.

[Synthesis Example 7]
Synthesis of 5- (2-chloro-5-fluoro-3- (methylthio) phenyl) -6- (2,6-difluoro-4- (methylthio) phenyl) -1-ethylpyridin-2 (1H) -one ( Compound No. 15)

166 mg of 5- (2-chloro-3,5-difluorophenyl) -1-ethyl-6- (2,4,6-trifluorophenyl) pyridin-2 (1H) -one synthesized with reference to Reference Example 2. And a DMF solution containing 44 mg of sodium methanethiolate was stirred at 60 ° C.
After cooling to room temperature, water and ethyl acetate were added to the reaction mixture for liquid separation. The obtained organic layer was washed with saturated saline and dried over sodium sulfate. The obtained residue was purified by silica gel column chromatography. The title compound was obtained as 87 mg of a white solid.

[Synthesis Example 8]
Step 1: 5- (2-chloro-3,5-dimethoxyphenyl) -6- (2,6-difluoro-4-((trimethylsilyl) ethynyl) phenyl) -1-ethylpyridin-2 (1H) -one Synthesis

  6- (4-bromo-2,6-difluorophenyl) -5- (2-chloro-3,5-dimethoxyphenyl) -1-ethylpyridin-2 (1H) -one synthesized with reference to Reference Example 2. A THF solution containing 90 mg, 78 μl of triethylamine, 77 μl of trimethylsilylacetylene, 43 mg of tetrakis (triphenylphosphine) palladium and 7 mg of copper iodide was stirred at 70 ° C. for 5 hours. Further, 1 ml of trimethylsilylacetylene and 129 mg of tetrakis (triphenylphosphine) palladium were added, and the mixture was stirred at 70 ° C. for 3 hours. After cooling to room temperature, a saturated aqueous ammonium chloride solution and ethyl acetate were added to the reaction mixture, and the mixture was separated. The obtained organic layer was washed with saturated saline and dried over sodium sulfate. The obtained residue was purified by silica gel column chromatography. The title compound was obtained as 91 mg of a yellow oil.

_{^{1 H-NMR (CDCl 3)}} δ: 7.30 (1H, d, J = 9.5 Hz), 6.98 (1H, d, J = 9.5 Hz), 6.93-6.92 ( 1H, m), 6.72-6.71 (1H, m), 6.35 (1H, d, J = 2.7 Hz), 6.23 (1H, dd, J = 2.7, 1. 8 Hz), 3.90-3.82 (5H, m), 3.66 (3H, s), 1.13 (3H, t, J = 7.2 Hz), 0.24 (9H, s) .

Step 2: Synthesis of 5- (2-chloro-3,5-dimethoxyphenyl) -1-ethyl-6- (4-ethynyl-2,6-difluorophenyl) pyridin-2 (1H) -one (Compound No. 11) )

  91 mg of 5- (2-chloro-3,5-dimethoxyphenyl) -6- (2,6-difluoro-4-((trimethylsilyl) ethynyl) phenyl) -1-ethylpyridin-2 (1H) -one and potassium carbonate A methanol solution containing 75 mg was stirred at room temperature for 2 hours. A saturated aqueous ammonium chloride solution and ethyl acetate were added to the reaction mixture, and the mixture was separated. The obtained organic layer was washed with saturated saline and dried over sodium sulfate. The obtained residue was purified by silica gel column chromatography. The title compound was obtained as 77 mg of a white solid.

[Synthesis Example 9]
Synthesis of 3-chloro-5- (2-chlorophenyl) -6- (2,6-difluoro-4- (1H-pyrazol-1-yl) phenyl) -1-ethylpyridin-2 (1H) -one (Compound Number 19)

  3-chloro-5- (2-chlorophenyl) -1-ethyl-6- (2,4,6-trifluorophenyl) pyridin-2 (1H) -one synthesized with reference to Reference Example 2 and Synthesis Example 3. A DMSO solution containing 150 mg, 77 mg of pyrazole and 156 mg of potassium carbonate was stirred at 100 ° C. for 2 hours. After cooling to room temperature, water and ethyl acetate were added to the reaction mixture for liquid separation. The obtained organic layer was washed with saturated saline and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography. The title compound was obtained as 113 mg of a white solid.

[Synthesis Example 10]
3-chloro-5- (2-chlorophenyl) -6- (2,6-difluoro-4- (1H-1,2,4-triazol-1-yl) phenyl) -1-ethylpyridine-2 (1H) Synthesis of -one (Compound No. 20)

  3-chloro-5- (2-chlorophenyl) -1-ethyl-6- (2,4,6-trifluorophenyl) pyridin-2 (1H) -one synthesized with reference to Reference Example 2 and Synthesis Example 3. 3 ml of a DMSO solution containing 150 mg, 39 mg of 1,2,4-triazole and 78 mg of potassium carbonate was stirred at 100 ° C. for 1 hour. After cooling to room temperature, water and ethyl acetate were added to the reaction mixture for liquid separation. The obtained organic layer was washed with saturated saline and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography. The title compound was obtained as 92 mg of a white solid.

[Synthesis Example 11]
Synthesis of 3-chloro-5- (2-chlorophenyl) -6- (2,6-difluoro-4-((propane-2-ylideneamino) oxy) phenyl) -1-ethylpyridin-2 (1H) -one ( Compound No. 30)

  3-chloro-5- (2-chlorophenyl) -1-ethyl-6- (2,4,6-trifluorophenyl) pyridin-2 (1H) -one synthesized with reference to Reference Example 2 and Synthesis Example 3. 7 ml of a THF solution containing 100 mg, 55 mg of acetoxime and 30 mg of 60% sodium hydride was stirred at 70 ° C. for 3 hours. Further, 2 ml of DMF was added, followed by stirring at 70 ° C. for 30 minutes. After cooling to room temperature, a saturated aqueous ammonium chloride solution and ethyl acetate were added to the reaction mixture, and the mixture was separated. The obtained organic layer was sequentially washed with water and saturated saline, and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography. The title compound was obtained as 107 mg of a white solid.

[Synthesis Example 12]
Synthesis of 5- (2-chlorophenyl) -6- (2,6-difluoro-4- (2-methoxyethoxy) phenyl) -1-ethylpyridine-2 (1H) -thione (Compound No. 33)

  100 mg of 5- (2-chlorophenyl) -1-ethyl-6- (2,4,6-trifluorophenyl) pyridine-2 (1H) -thione synthesized in Reference Example 3 (Step 2), 60 mg of 2-methoxyethanol And 5 ml of a DMF solution containing 32 mg of 60% sodium hydride were stirred at room temperature for 20 minutes. A saturated aqueous ammonium chloride solution and ethyl acetate were added to the reaction mixture, and the mixture was separated. The obtained organic layer was sequentially washed with water and saturated saline, and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography. The title compound was obtained as 97 mg of a yellow solid.

[Synthesis Example 13]
Synthesis of 3-chloro-5- (2-chlorophenyl) -6- (4- (cyclopropylmethoxy) -2,6-difluorophenyl) -1-ethylpyridin-2 (1H) -one (Compound No. 21)

  3-chloro-5- (2-chlorophenyl) -1-ethyl-6- (2,4,6-trifluorophenyl) pyridine-2 (1H)-synthesized with reference to Reference Example 2 and Synthesis Example 3. 7 ml of a THF solution containing 100 mg of ON, 54 mg of cyclopropylmethanol and 45 mg of 60% sodium hydride was stirred at 60 ° C. for 4 hours. After cooling to room temperature, a saturated aqueous ammonium chloride solution and ethyl acetate were added to the reaction mixture, and the mixture was separated. The obtained organic layer was sequentially washed with water and saturated saline, and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography. The title compound was obtained as 70 mg of a white solid.

[Synthesis Example 14]
Synthesis of 6- (4- (benzyloxy) -2,6-difluorophenyl) -3-chloro-5- (2-chlorophenyl-1-ethylpyridin-2 (1H) -one (Compound No. 31)

  3-chloro-5- (2-chlorophenyl) -1-ethyl-6- (2,4,6-trifluorophenyl) pyridine-2 (1H)-synthesized with reference to Reference Example 2 and Synthesis Example 3. 7 ml of a THF solution containing 100 mg of ON, 82 mg of benzyl alcohol and 30 mg of 60% sodium hydride was stirred at room temperature for 9 hours. A saturated aqueous ammonium chloride solution and ethyl acetate were added to the reaction mixture, and the mixture was separated. The obtained organic layer was sequentially washed with water and saturated saline, and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography. This solid was washed with a mixed solvent of ethyl acetate and diisopropyl ether to give the title compound as a white solid (36 mg).

[Synthesis Example 15]
Synthesis of 3-chloro-5- (2-chlorophenyl) -6- (2,6-difluoro-4- (4-methoxyphenoxy) phenyl) -1-ethylpyridin-2 (1H) -one (Compound No. 32)

  3-chloro-5- (2-chlorophenyl) -1-ethyl-6- (2,4,6-trifluorophenyl) pyridin-2 (1H) -one synthesized with reference to Reference Example 2 and Synthesis Example 3. 7 ml of a THF solution containing 100 mg, 94 mg of 4-methoxyphenol and 30 mg of 60% sodium hydride was stirred at room temperature for 2 hours. A saturated aqueous ammonium chloride solution and ethyl acetate were added to the reaction mixture, and the mixture was separated. The obtained organic layer was sequentially washed with water and saturated saline, and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography. The title compound was obtained as 74 mg of a clear oil.

[Synthesis Example 16]
Synthesis of 4- (5-chloro-3- (2-chlorophenyl) -1-ethyl-6-oxo-1,6-dihydropyridin-2-yl) -3,5-difluorophenyl acetate (Compound No. 25)

  3-chloro-5- (2-chlorophenyl) -6- (2,6-difluoro-4-hydroxyphenyl) -1-ethylpyridine-2 (1H) synthesized with reference to Reference Example 2 and Synthesis Example 3. 2 ml of a dichloromethane solution containing 119 mg of -one, 154 mg of acetic anhydride and 48 mg of pyridine was stirred at room temperature for 1 hour. Hydrochloric acid and dichloromethane were added to the reaction mixture for liquid separation. The obtained organic layer was sequentially washed with water and saturated saline, and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography. The title compound was obtained as 116 mg of a white solid.

[Synthesis Example 17]
Synthesis of 5- (2-chlorophenyl) -6- (2,6-difluoro-4- (2-methoxyethoxy) phenyl) -1-ethyl-3-methylpyridin-2 (1H) -one (Compound No. 26)

  100 mg of 5- (2-chlorophenyl) -1-ethyl-3-methyl-6- (2,4,6-trifluorophenyl) pyridin-2 (1H) -one synthesized in Reference Example 4, 60 mg of methoxyethanol and 60 mg of methoxyethanol 7 ml of a dichloromethane solution containing 32 mg of sodium hydride was stirred at room temperature for 4 hours. A saturated aqueous ammonium chloride solution and ethyl acetate were added to the reaction mixture, and the mixture was separated. The obtained organic layer was sequentially washed with water and saturated saline, and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography. The title compound was obtained as 78 mg of a clear oil.

[Synthesis Example 18]
Synthesis of 5- (2-chlorophenyl) -6- (2,6-difluoro-4- (propyn-2-yl-1-oxy) phenyl) -1-ethylpyridine-2 (1H) -thione (Compound No. 37) )

  To 5 ml of a THF solution containing 44 mg of propargyl alcohol was added 32 mg of 60% sodium hydride, and the mixture was stirred at room temperature for 10 minutes. Next, 5 ml of a THF solution containing 100 mg of 3-chloro-5- (2-chlorophenyl) -1-ethyl-6- (2,4,6-trifluorophenyl) pyridin-2 (1H) -one was added to the reaction mixture. And stirred at room temperature for 3 hours. A saturated aqueous ammonium chloride solution and ethyl acetate were added to the reaction mixture, and the mixture was separated. The obtained organic layer was sequentially washed with water and saturated saline, and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography. The title compound was obtained as 97 mg of an orange oil.

[Synthesis Example 19]
Synthesis of 3-chloro-5- (2-chlorophenyl) -6- (2,6-difluoro-4- (methylamino) phenyl) -1-ethylpyridin-2 (1H) -one (Compound No. 38)

  3-chloro-5- (2-chlorophenyl) -1-ethyl-6- (2,4,6-trifluorophenyl) pyridin-2 (1H) -one synthesized with reference to Reference Example 2 and Synthesis Example 3. 2 ml of a DMF solution containing 200 mg and 2 ml of 40% aqueous methylamine solution was stirred at room temperature for 24 hours. Water was added to the reaction mixture, and the precipitated solid was filtered. The obtained solid was dissolved in ethyl acetate and purified by silica gel column chromatography. The title compound was obtained as 122 mg of a white solid.

[Synthesis Example 20]
Synthesis of 3-chloro-5- (2-chlorophenyl) -6- (4- (dimethylamino) -2,6-difluorophenyl) -1-ethylpyridin-2 (1H) -one (Compound No. 39)

  70 mg of 3-chloro-5- (2-chlorophenyl) -6- (2,6-difluoro-4- (methylamino) phenyl) -1-ethylpyridin-2 (1H) -one, 22 μl of methyl iodide and 60% 2 ml of a THF solution containing 14 mg of sodium hydride was stirred at room temperature for 3 hours. Water and ethyl acetate were added to the reaction mixture, and the mixture was separated. The obtained organic layer was sequentially washed with water and saturated saline, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography. The title compound was obtained as 64 mg of a white solid.

<Reference Example 1>
Step 1: Synthesis of ethyl 4- (2-chlorophenyl) -5-oxo-5- (4-cyano-2,6-difluorophenyl) pentanoate

  To 5 ml of a THF solution containing 786 mg of 4- (2- (2-chlorophenyl) acetyl) -3,5-difluorobenzonitrile, 29 mg of potassium t-butoxide and 311 μl of ethyl acrylate were added, and the mixture was stirred at 50 ° C. for 3 hours. Further, 58 mg of potassium t-butoxide was added, and the mixture was stirred at 50 ° C for 4 hours. After cooling to room temperature, a saturated aqueous ammonium chloride solution and ethyl acetate were added to the reaction mixture, and the mixture was separated. The obtained organic layer was washed with saturated saline and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography. The title compound was obtained as 394 mg of a colorless oil.

¹ H-NMR (CDCl ₃ ) δ: 7.33-7.31 (1H, m), 7.28-7.18 (3H, m), 7.16-7.15 (1H, m), 7 .13-7.13 (1H, m), 4.91 (1H, t, J = 7.3 Hz), 4.12 (2H, q, J = 7.1 Hz), 2.61-2. 56 (1H, m), 2.35-2.30 (2H, m), 2.17-2.14 (1H, m), 1.25 (3H, t, J = 7.1 Hz).

Step 2: Synthesis of 4- (2-chlorophenyl) -5-oxo-5- (4-cyano-2,6-difluorophenyl) pentanoic acid

  0.78 ml of a 10% aqueous sodium hydroxide solution was added to 3 ml of an ethanol solution containing 394 mg of ethyl 4- (2-chlorophenyl) -5-oxo-5- (4-cyano-2,6-difluorophenyl) pentanoate, Stirred at room temperature for 2 hours. A saturated aqueous ammonium chloride solution and ethyl acetate were added to the reaction mixture, and the mixture was separated. The obtained organic layer was washed with saturated saline and dried over sodium sulfate. The solvent was distilled off under reduced pressure to obtain 361 mg of the title compound as a colorless transparent gum. Used for the next reaction without further purification.

¹ H-NMR (CDCl ₃ ) δ: 7.40-7.09 (6H, m), 4.89-4.87 (1H, m), 4.25-4.22 (1H, m), 2 .57-2.54 (1H, m), 2.36-2.32 (2H, m), 2.16-2.05 (1H, m).

<Reference Example 2>
Step 1: Synthesis of N ′-(3,5-dimethoxybenzylidene) -4-methylbenzenesulfonylhydrazide

  A 100 ml ethanol solution containing 10.0 g of 3,5-dimethoxybenzaldehyde and 11.2 g of 4-methylbenzenesulfonylhydrazide was stirred at room temperature for 5 hours. After evaporating the obtained reaction mixture under reduced pressure, the title compound was obtained as 20.0 g of a yellow solid.

¹ H-NMR (CDCl ₃ ) δ: 8.13 (1H, s), 7.87 (2H, d, J = 7.8 Hz), 7.68 (1H, s), 7.30 (2H, s) d, J = 7.8 Hz), 6.72 (2H, d, J = 2.4 Hz), 6.46 (1H, t, J = 2.4 Hz), 3.79 (6H, s) , 2.40 (3H, s).

Step 2: Synthesis of 2- (3,5-dimethoxyphenyl) -1- (2,4,6-trifluorophenyl) ethanone

  20 ml of an aqueous solution in which 0.80 g of sodium hydroxide was dissolved in 100 ml of an aqueous solution containing 6.68 g of N '-(3,5-dimethoxybenzylidene) -4-methylbenzenesulfonyl hydrazide and 2,4,6-trifluorobenzaldehyde 60 g was added and the mixture was stirred at 80 ° C. for 90 minutes. After cooling to room temperature, ethyl acetate was added to the reaction mixture for liquid separation. The obtained organic layer was washed successively with a saturated aqueous solution of ammonium chloride and a saturated saline solution, and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography. The title compound was obtained as 1.85 g of a yellow oil.

¹ H-NMR (CDCl ₃ ) δ: 6.68-6.66 (2H, m), 6.35 (3H, s), 4.06 (2H, s), 3.75 (6H, s).

Step 3: Synthesis of ethyl 4- (3,5-dimethoxyphenyl) -5-oxo-5- (2,4,6-trifluorophenyl) pentanoate

  To 18 ml of a THF solution containing 1.85 g of 2- (3,5-dimethoxyphenyl) -1- (2,4,6-trifluorophenyl) ethanone was added 67 mg of potassium t-butoxide and 714 μl of ethyl acrylate, and the mixture was added to ice. The mixture was stirred overnight under cooling. A saturated aqueous ammonium chloride solution and ethyl acetate were added to the reaction mixture, and the mixture was separated. The obtained organic layer was washed with saturated saline and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography. The title compound was obtained as 1.51 g of a brown oil.

_{^{1 H-NMR (CDCl 3)}} δ: 6.61-6.57 (2H, m), 6.31-6.29 (3H, m), 4.19 (1H, t, J = 7.3 Hz ), 4.13 (2H, q, J = 7.1 Hz), 3.73 (6H, s), 2.49-2.47 (1H, m), 2.30 (2H, t, J = 7.5 Hz), 2.09-2.07 (1H, m), 1.25 (3H, t, J = 7.1 Hz)

Step 4: Synthesis of 4- (3,5-dimethoxyphenyl) -5-oxo-5- (2,4,6-trifluorophenyl) pentanoic acid

  15 ml of an acetic acid solution containing 1.51 g of ethyl 4- (3,5-dimethoxyphenyl) -5-oxo-5- (2,4,6-trifluorophenyl) pentanoate and 3 ml of concentrated hydrochloric acid was stirred at 60 ° C. for 3 hours. did. After cooling to room temperature, water and ethyl acetate were added to the reaction mixture for liquid separation. The obtained organic layer was sequentially washed with water and saturated saline, and dried over sodium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound. It was used for the next step reaction without further purification.

Step 5: Synthesis of 5- (3,5-dimethoxyphenyl) -6- (2,4,6-trifluorophenyl) -3,4-dihydropyridin-2 (1H) -one

  14.18 g of ammonium acetate and 15 ml of acetic acid are added to the unpurified 4- (3,5-dimethoxyphenyl) -5-oxo-5- (2,4,6-trifluorophenyl) pentanoic acid obtained in Step 4. In addition, the mixture was stirred at 120 ° C. for 10 hours. After cooling to room temperature, water and ethyl acetate were added to the reaction mixture for liquid separation. The obtained organic layer was washed successively with a saturated aqueous solution of sodium hydrogen carbonate and a saturated saline solution, and dried over sodium sulfate. After evaporating the solvent under reduced pressure, the obtained solid was washed with isopropyl ether. The title compound was obtained as 0.99 g of a brown solid.

¹ H-NMR (CDCl ₃ ) δ: 6.68 (1H, s), 6.62 (2H, td, J = 8.7, 1.4 Hz), 6.26 (1H, t, J = 2) .1 Hz), 6.16 (2H, d, J = 2.1 Hz), 3.65 (6H, s), 2.87-2.86 (2H, m), 2.73-2.71 (2H, m).

Step 6: Synthesis of 5- (3,5-dimethoxyphenyl) -1-methyl-6- (2,4,6-trifluorophenyl) -3,4-dihydropyridin-2 (1H) -one

  343 mg of 5- (3,5-dimethoxyphenyl) -6- (2,4,6-trifluorophenyl) -3,4-dihydropyridin-2 (1H) -one, 176 μl of methyl iodide and 1.85 g of cesium carbonate The DMF solution containing 6 ml was stirred at room temperature for 3 hours. Water and ethyl acetate were added to the reaction mixture, and the mixture was separated. The obtained organic layer was washed successively with water, an aqueous solution of sodium thiosulfate and saturated saline, 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 346 mg of a white solid.

¹ H-NMR (CDCl ₃ ) δ: 6.62-6.60 (2H, m), 6.23 (1H, t, J = 2.1 Hz), 6.13 (2H, d, J = 2) .1 Hz), 3.65 (6H, s), 2.87 (3H, s), 2.76-2.74 (4H, m).

Step 7: Synthesis of 5- (3,5-dimethoxyphenyl) -1-methyl-6- (2,4,6-trifluorophenyl) pyridin-2 (1H) -one

  Contains 320 mg of 5- (3,5-dimethoxyphenyl) -1-methyl-6- (2,4,6-trifluorophenyl) -3,4-dihydropyridin-2 (1H) -one and 4.42 g of manganese dioxide. 12 ml of a dichloromethane solution was stirred for 5 hours while heating under reflux. After cooling to room temperature, the reaction mixture was filtered through celite. After the solvent was distilled off from the filtrate under reduced pressure, the obtained residue was purified by silica gel column chromatography. The title compound was obtained as 263 mg of a white solid.

¹ H-NMR (CDCl ₃ ) δ: 7.41 (1H, d, J = 9.5 Hz), 6.74 (1H, d, J = 9.5 Hz), 6.68-6.66 (1H, d, J = 9.5 Hz) 2H, m), 6.30 (1H, t, J = 2.3 Hz), 6.19 (2H, d, J = 2.3 Hz), 3.68 (6H, s), 3.37 ( 3H, s).

Step 8: Synthesis of 5- (2-chloro-3,5-dimethoxyphenyl) -1-methyl-6- (2,4,6-trifluorophenyl) pyridin-2 (1H) -one

  6 ml of a DMF solution containing 163 mg of 5- (3,5-dimethoxyphenyl) -1-methyl-6- (2,4,6-trifluorophenyl) pyridin-2 (1H) -one and 64 mg of N-chlorosuccinimide was Stirred at 80 ° C. for 5 hours. Further, 45 mg of N-chlorosuccinimide was added, and the mixture was stirred at 100 ° C. for 4 hours. After cooling to room temperature, water and ethyl acetate were added to the reaction mixture for liquid separation. The obtained organic layer was sequentially washed with an aqueous solution of sodium thiosulfate and a saturated saline solution, 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 150 mg of a white solid.

¹ H-NMR (CDCl ₃ ) δ: 7.33 (1H, d, J = 9.5 Hz), 6.75 (1H, d, J = 9.5 Hz), 6.68-6.66 ( 1H, m), 6.63-6.62 (1H, m), 6.38 (1H, d, J = 2.8 Hz), 6.19 (1H, dd, J = 2.8, 1. 8 Hz), 3.83 (3H, s), 3.67 (3H, s), 3.37 (3H, s).

Step 9: Synthesis of 5- (2-chloro-3,5-dimethoxyphenyl) -1-methyl-6- (4-t-butoxy-2,6-difluorophenyl) pyridin-2 (1H) -one

  THF containing 700 mg of 5- (2-chloro-3,5-dimethoxyphenyl) -1-methyl-6- (2,4,6-trifluorophenyl) pyridin-2 (1H) -one and 383 mg of potassium t-butoxy. 14 ml of the solution was stirred at room temperature for 8 hours. A saturated aqueous ammonium chloride solution and ethyl acetate were added to the reaction mixture, and the mixture was separated. The obtained organic layer was washed with saturated saline 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 694 mg of a white solid.

¹ H-NMR (CDCl ₃ ) δ: 7.35 (1H, d, J = 9.5 Hz), 6.73 (1H, d, J = 9.5 Hz), 6.51 (1H, dt, J = 10.7, 1.8 Hz), 6.43 (1H, dt, J = 10.3, 1.8 Hz), 6.34 (1H, d, J = 2.8 Hz), 6. 16 (1H, dd, J = 2.6, 1.4 Hz), 3.82 (3H, s), 3.63 (3H, s), 3.41 (3H, s), 1.35 (9H , S).

Step 10: Synthesis of 5- (2-chloro-3,5-dimethoxyphenyl) -1-methyl-6- (2,6-difluoro-4-hydroxyphenyl) pyridin-2 (1H) -one

  614 mg of 5- (2-chloro-3,5-dimethoxyphenyl) -1-methyl-6- (4-t-butoxy-2,6-difluorophenyl) pyridin-2 (1H) -one and 3 ml of trifluoroacetic acid 30 ml of the dichloromethane solution containing was stirred at room temperature for 13 hours. A saturated aqueous solution of sodium hydrogen carbonate and ethyl acetate were added to the reaction mixture, and the mixture was separated. The obtained organic layer was washed with saturated saline and dried over sodium sulfate. After evaporating the solvent under reduced pressure, the obtained solid was washed with isopropyl ether and dichloromethane. The title compound was obtained as 518 mg of a white solid.

¹ H-NMR (DMSO-D ₆ ) δ: 7.39 (1H, d, J = 9.5 Hz), 6.59 (1H, d, J = 9.5 Hz), 6.57 (1H, d, J = 2.8 Hz), 6.53-6.51 (1H, m), 6.40-6.39 (1H, m), 6.15 (1H, d, J = 2.8 Hz) ), 3.80 (3H, s), 3.63 (3H, s), 3.23 (3H, s).

<Reference Example 3>
Step 1: Synthesis of 5- (2-chlorophenyl) -1-ethyl-6- (2,4,6-trifluorophenyl) -3,4-dihydropyridine-2 (1H) -thione

  1.0 g of 5- (2-chlorophenyl) -1-ethyl-6- (2,4,6-trifluorophenyl) -3,4-dihydropyridin-2 (1H) -one synthesized with reference to Reference Example 2, 20 ml of a toluene solution containing 1.2 g of Lawson's reagent was stirred under heating and refluxing for 1.5 hours. After cooling to room temperature, methanol, water and ethyl acetate were added to the reaction mixture, and the mixture was separated. The obtained organic layer was washed with saturated saline and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography. The title compound was obtained as 992 mg of a yellow solid.

¹ H-NMR (CDCl ₃ ) δ: 7.29 (1H, dd, J = 7.9, 1.2 Hz), 7.12 (1H, ddd, J = 7.9, 7.5, 1.5). 7.7 Hz), 7.05 (1H, ddd, J = 7.6, 7.5, 1.2 Hz), 6.99 (1H, dt, J = 7.6, 1.7 Hz), 6. 60 (1H, tt, J = 8.8, 2.2 Hz), 6.53 (1H, tt, J = 8.8, 2.2 Hz), 4.18-4.11 (1H, m) , 3.95-3.92 (1H, m), 3.43-3.35 (1H, m), 3.28-3.24 (1H, m), 2.72-2.68 (1H, m) m), 2.50-2.42 (1H, m), 1.11 (3H, t, J = 7.1 Hz).

Step 2: Synthesis of 5- (2-chlorophenyl) -1-ethyl-6- (2,4,6-trifluorophenyl) pyridine-2 (1H) -thione

  To 30 ml of a carbon tetrachloride solution containing 992 mg of 5- (2-chlorophenyl) -1-ethyl-6- (2,4,6-trifluorophenyl) -3,4-dihydropyridine-2 (1H) -thione was added N- 486 mg of bromosuccinimide and 43 mg of azobisisobutyronitrile were added, and the mixture was stirred at 80 ° C for 5.5 hours. After cooling to room temperature, an aqueous solution of sodium thiosulfate, water and dichloromethane were added to the reaction mixture, and the mixture was separated. The obtained organic layer was sequentially washed with water 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 968 mg of a yellow oil.

_{^{1 H-NMR (CDCl 3)}} δ: 7.85 (1H, d, J = 8.8 Hz), 7.33 (1H, dd, J = 8.1, 1.2 Hz), 7.20- 7.18 (1H, m), 7.13 (1H, d, J = 8.8 Hz), 7.10-7.08 (1H, m), 7.04-7.02 (1H, m) , 6.69-6.59 (2H, m), 4.59-4.57 (2H, m), 1.28 (3H, t, J = 7.0 Hz).

<Reference Example 4>
Synthesis of 5- (2-chlorophenyl) -1-ethyl-3-methyl-6- (2,4,6-trifluorophenyl) pyridin-2 (1H) -one

  3-bromo-5- (2-chlorophenyl) -1-ethyl-6- (2,4,6-trifluorophenyl) pyridin-2 (1H) -one synthesized with reference to Reference Example 2 and Synthesis Example 3. A mixed solution of 400 mg, 216 mg of methylboronic acid, 10 mg of palladium (II) acetate, 671 mg of tripotassium phosphate, 25 mg of tricyclohexylphosphine, 20 ml of toluene and 2 ml of water was stirred at 100 ° C. for 7 hours. After cooling to room temperature, a saturated aqueous ammonium chloride solution and ethyl acetate were added to the reaction mixture, and the mixture was separated. The obtained organic layer was washed with saturated saline 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 327 mg of a yellow solid.

¹ H-NMR (CDCl ₃ ) δ: 7.32-7.30 (1H, m), 7.21 (1H, q, J = 1.1 Hz), 7.15-7.13 (1H, m) ), 7.07-7.05 (2H, m), 6.63 (1H, tt, J = 8.6, 2.1 Hz), 6.58 (1H, tt, J = 8.6, 2). 3.1 Hz), 3.92-3.90 (2H, m), 2.25 (3H, d, J = 1.1 Hz), 1.16 (3H, t, J = 7.2 Hz).

  Table 4 shows compounds synthesized according to the above Examples, but the present invention is not limited to these.

In Table 4, structure A shows the following.

In Table 4, Structure B shows the following.

In Table 4, structure C shows the following.

In Table 4, Structure D shows the following.

Next, about the compounds described in Table 4, Table ¹ shows ¹ H-NMR data thereof.

  Next, it is specifically shown that the compound of the present invention is effective for plant diseases, but the present invention is not limited to these examples.

[Test Example A] Rice blast A seed of a test plant (rice cultivar: Kofu) was sown, and then cultivated until the second leaf developed. In the test, the compound of the present invention was dissolved in a dimethyl sulfoxide-methanol mixed solution (volume ratio: 9/1), and diluted with well water to a concentration of 250 ppm to obtain a drug solution. The obtained drug solution was sprayed on the test plant (2.5 ml / pot). After the chemical solution was dried, the plants were spray-inoculated with a conidia suspension of 1-2 × 10 ⁵ cells / ml of rice blast fungus (Magnaporthe grisea). After the inoculation, the cells were allowed to stand in a wet room at room temperature of 20 to 23 ° C. for about 24 hours to promote the onset of the disease. The onset of disease 6 to 10 days after inoculation was investigated, and the effect of the drug solution was evaluated.

[Test Example B] Tomato gray mold A seed of a test plant (tomato variety: large-scale fukuju) was sown, and then cultivated until 3 to 5 true leaves developed. In the test, the compound of the present invention was dissolved in a dimethyl sulfoxide-methanol mixed solution (volume ratio: 9/1), and diluted with well water to a concentration of 250 ppm to obtain a drug solution. The obtained drug solution was sprayed on the test plant (2.5 ml / pot). After the chemical solution was dried, the plants were spray-inoculated with a conidia suspension of Botrytis cinerea at 4 to 8 × 10 ⁵ cells / ml. After the inoculation, the cells were left in a wet room at room temperature of 20 to 23 ° C. for about 48 hours to promote the onset of the disease. The onset of disease 2-3 days after inoculation was investigated, and the effect of the drug solution was evaluated.

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

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

[Test Example E] Wheat leaf rust Seeds of a test plant (wheat variety: Norin 61) were sown and then cultivated until the first leaves developed. In the test, the compound of the present invention was dissolved in a dimethyl sulfoxide-methanol mixed solution (volume ratio: 9/1), and diluted with well water to a concentration of 250 ppm to obtain a drug solution. The obtained drug solution was sprayed on the test plant (2.5 ml / pot). After the medicinal solution was dried, the plants were spray-inoculated with a uredospore suspension of wheat leaf rust (Puccinia recondita) at 1 to 2 × 10 ⁵ cells / ml. After the inoculation, the cells were allowed to stand in a wet room at room temperature of 20 to 23 ° C. for about 24 hours to promote the onset of the disease. The degree of onset 7 to 10 days after inoculation was investigated, and the effect of the drug solution was evaluated.

[Test Example F] Tomato Blight After sowing seeds of a test plant (tomato variety: large fukuju), they were cultivated until 3 to 5 true leaves developed. In the test, the compound of the present invention was dissolved in a dimethyl sulfoxide-methanol mixed solution (volume ratio: 9/1), and diluted with well water to a concentration of 250 ppm to obtain a drug solution. The obtained drug solution was sprayed on the test plant (2.5 ml / pot). After the chemical solution was dried, the plants were spray-inoculated with a zoospore suspension of 4 to 8 × 10 ³ cells / ml of Phytophthora infestans. After the inoculation, the cells were allowed to stand in a wet room at room temperature of 20 ° C. for about 24 hours to promote the onset of the disease. The degree of onset 5 to 10 days after inoculation was investigated, and the effect of the drug solution was evaluated.

[Test Example G] Grape downy mildew After sowing seeds of a test plant (grape variety: Neo Muscat), they were cultivated until three to four true leaves were developed. In the test, the compound of the present invention was dissolved in a dimethyl sulfoxide-methanol mixed solution (volume ratio: 9/1), and diluted with well water to a concentration of 250 ppm to obtain a drug solution. The obtained drug solution was sprayed on the test plant (2.5 ml / pot). After the medicinal solution was dried, the plants were spray-inoculated with a zoospore suspension of 1-2 × 10 ⁴ vines / ml of downy mildew of Plasmopara viticola. After the inoculation, the cells were allowed to stand in a wet room at room temperature of 20 ° C. for about 24 hours to promote the onset of the disease. The degree of onset 7 to 10 days after inoculation was investigated, and the effect of the drug solution was evaluated.

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

  With respect to the degree of disease in the above test examples, the degree of disease was evaluated for each 0.05, with the degree of disease occurring in uninfected plants being 0 and the degree of disease occurring in plants in the untreated area being set to 3. Further, the control value was calculated from the degree of onset according to the following formula.

<Control value>
Control value = 100 {1- (n / 3)}
n = Disease severity in each treatment zone

  Table 6 summarizes the above test results. In the table, H indicates that the control value is greater than 50%, and L indicates that the control value is 50% or less. In addition, nt indicates that the test was not performed.

  Since the pyridone compound of the present invention is a novel compound and can control plant diseases, it is useful as a pesticide, for example, a pesticide for agricultural and horticultural use, particularly a fungicide for agricultural and horticultural use.

  The disclosure of Japanese Patent Application No. 2017-77800 (filing date: April 10, 2017) is incorporated herein by reference in its entirety.

  All documents, patent applications, and technical standards mentioned herein are to the same extent as if each individual document, patent application, and technical standard were specifically and individually stated to be incorporated by reference. Incorporated herein by reference.

Claims (8)

Equation (1)

Wherein R1 is
Hydroxyl group,
Cyano group,
A C1-C6 alkyl group optionally substituted with a substituent A,
A C1-C6 haloalkyl group,
A C3-C8 cycloalkyl group optionally substituted with a substituent A,
A C2-C6 alkenyl group optionally substituted with a substituent A,
A C2-C6 haloalkenyl group,
A C2-C6 alkynyl group optionally substituted with a substituent A,
A C2-C6 haloalkynyl group,
A C1-C6 alkoxy group optionally substituted with a substituent A,
A C1-C6 haloalkoxy group,
A C3-C8 cycloalkoxy group optionally substituted with a substituent A,
A C2-C6 alkenyloxy group optionally substituted with a substituent A,
A C2-C6 haloalkenyloxy group,
A C3-C6 alkynyloxy group optionally substituted with a substituent A,
A C3-C6 haloalkynyloxy group,
Or R10R11N- (wherein R10 and R11 are each independently a hydrogen atom or a C1-C6 alkyl group);
R2 is
Hydroxyl group,
Cyano group,
Nitro group,
Halogen atom,
A C1-C6 alkyl group optionally substituted with a substituent B,
A C1-C6 haloalkyl group,
A C3-C8 cycloalkyl group optionally substituted with a substituent B,
A C2-C6 alkenyl group optionally substituted with substituent B,
A C2-C6 haloalkenyl group,
A C2-C6 alkynyl group optionally substituted with a substituent B,
A C2-C6 haloalkynyl group,
A C1-C6 alkoxy group optionally substituted with a substituent B,
A C1-C6 haloalkoxy group,
A C3-C8 cycloalkoxy group optionally substituted with a substituent B,
A C2-C6 alkenyloxy group optionally substituted with a substituent B,
A C2-C6 haloalkenyloxy group,
A C3-C6 alkynyloxy group optionally substituted with a substituent B,
A C3-C6 haloalkynyloxy group,
R20C (= O)-(where R20 is a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, A C3-C8 cycloalkoxy group, or R21R22N- (wherein R21 and R22 are each independently a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B1, a C1-C6 Represents a haloalkyl group, or a C3-C8 cycloalkyl group, or R21 and R22, together with the nitrogen atom to which they are attached, represent an aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl, homopiperidinyl, or azocanyl group; Represents what is formed.).),
R20C (= O) O- (where R20 has the same meaning as described above),
R21R22N- (where R21 and R22 are as defined above),
R23-L2- (wherein, R23 represents an alkyl group or a haloalkyl group of C1 -C6, a C1 -C6, L2 represents S, SO, or SO _2.),
R24C (= O) N (R25)-(where R24 is a hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1 Represents a haloalkoxy group of C6 to C6, a cycloalkoxy group of C3 to C8, or R21R22N- (where R21 and R22 have the same meanings as described above), and R25 is appropriately substituted with a hydrogen atom or a substituent B1. Represents a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, or a C3 to C8 cycloalkyl group.)
Or a 3- to 6-membered ring group containing 1 to 2 oxygen atoms;
R3 is
Hydrogen atom,
Nitro group,
Halogen 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 C1-C6 alkoxy group optionally substituted with a substituent C,
A C1-C6 haloalkoxy group,
R30-L3- (where R30 has the same meaning as R23, and L3 has the same meaning as L2);
R31R32N- (where R31 and R32 have the same meanings as R21 and R22 described above),
Or R33C (= O)-(where R33 represents a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group);
n represents an integer of 0 to 5 (however, when n is 2 or more, 2 or more R2 represents an independent substituent);
X represents an oxygen atom or a sulfur atom;
Y is
A phenyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, a thienyl group, a thiazolyl group, or an isothiazolyl group;
In the phenyl group, the substituent D is substituted at the ortho position, the substituent D1 is independently substituted with 0 to 3 as appropriate, and further the substituent D2 is independently substituted with 1 to 4 as appropriate.
In the pyridyl group, the pyridazinyl group, the pyrimidinyl group, the pyrazinyl group, or the triazinyl group, the substituent D is substituted at the ortho position, and the substituents D1 are each independently optionally substituted with 0 to 2, and further substituted. Groups D2 are each independently appropriately substituted with 1 to 3,
In the thienyl group, the thiazolyl group, or the isothiazolyl group, the substituent D is substituted at the ortho position, the substituents D1 are each independently optionally substituted with 0 to 1, and the substituents D2 are each independently substituted. Substitute 1-2 as appropriate;
A bond containing a broken line represents a double bond or a single bond;
And the substituent A is
Hydroxyl group, cyano group, C3-C8 cycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group, R12R13N- (where R12 and R13 are each independently And represents a hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group, or R12 and R13 together with the bonding nitrogen atom form an aziridinyl group , Azetidinyl group, pyrrolidinyl group, piperidinyl group, homopiperidinyl group, or azocanyl group), and R14-L1- (where R14 is a C1-C6 alkyl group, or a C1-C6 haloalkyl). represents a group, is selected L1 is, S, SO, or from the group consisting of.) representing the SO _2, At least one of the following:
Substituent B 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, R21R22N- R21 and R22 are as defined above, R23-L2- (where R23 and L2 are as defined above), R26R27R28Si- (where R26, R27 and R28 are each independently represents an alkyl group having C1~C6 _{have.), R26R27R28Si- (CH 2)} s-O- ( wherein, s represents an integer of 1 to 3, R26, R27 and R28 is a as defined above ), R20C (= O)-(where R20 has the same meaning as described above), and a 3- to 6-membered ring group containing 1 to 2 oxygen atoms. That is at least one selected from the group;
The substituent B1 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, R31R32N- (where R31 and R32 are the aforementioned R21 And R22 and R30-L3- (where R30 has the same meaning as R23, and L3 has the same meaning as L2). Species;
Substituent D is
At least one selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, and a C1-C6 haloalkoxy group;
The substituent D1 is
Hydroxyl group, halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, and C3-C8 cycloalkoxy group At least one selected from the group consisting of:
The substituent D2 is
Cyano group,
Nitro group,
A C2-C6 alkenyl group optionally substituted with substituent B,
A C2-C6 haloalkenyl group,
A C2-C6 alkynyl group optionally substituted with a substituent B,
A C2-C6 haloalkynyl group,
A C2-C6 alkenyloxy group optionally substituted with a substituent B,
A C2-C6 haloalkenyloxy group,
A C3-C6 alkynyloxy group optionally substituted with a substituent B,
A C3-C6 haloalkynyloxy group,
A C2-C6 alkoxyalkoxy group,
A C2-C6 cyanoalkoxy group,
A C4-C9 cycloalkylalkoxy group,
An aryl group optionally substituted with a substituent D,
A heteroaryl group optionally substituted with a substituent D,
An aryloxy group optionally substituted with a substituent D,
A heteroaryloxy group optionally substituted with a substituent D,
An aralkyloxy group optionally substituted with a substituent D,
R40 (CH2) pU- (where p represents an integer of 1 to 3, and R40 is a 3- to 6-membered ring group containing 1 to 2 oxygen atoms, R41R42N- (where R41 and R42 has the same meaning as R21 and R22 described above; or R43-L4- (where R43 has the same meaning as R14, and L4 has the same meaning as L1); U represents an oxygen atom or a sulfur atom.),
R41R42N- (where R41 and R42 are as defined above),
R43-L4- (where R43 has the same meaning as R14, and L4 has the same meaning as L1);
R44C (＝ O)-(where R44 is a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group which may be appropriately substituted with a substituent B A group, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group, or R41R42N- (where R41 and R42 have the same meanings as described above),
R44C (= O) O- (where R44 is as defined above),
R45C (＝ O) N (R46)-(where R45 is a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl A group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or R41R42N- (where R41 and R42 have the same meanings as described above); A hydrogen atom, a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, or a C3 to C8 cycloalkyl group which may be appropriately substituted with a substituent A);
R47R48C = N-O- (where R47 and R48 are each independently a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C Represents a C8 cycloalkyl group, a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group, or R41R42N- (where R41 and R42 have the same meanings as described above). .),
And at least one member selected from the group consisting of a 3- to 6-membered ring group containing 1 or 2 oxygen atoms.] Or a salt thereof. R1 is
Cyano group,
A C1-C6 alkyl group optionally substituted with a substituent A,
A C1-C6 haloalkyl group,
A C3-C8 cycloalkyl group optionally substituted with a substituent A,
A C2-C6 alkenyl group optionally substituted with a substituent A,
A C2-C6 haloalkenyl group,
A C2-C6 alkynyl group optionally substituted with a substituent A,
Or R10R11N- (wherein R10 and R11 are each independently a hydrogen atom or a C1-C6 alkyl group);
R2 is
Hydroxyl group,
Cyano group,
Halogen atom,
A C1-C6 alkyl group optionally substituted with a substituent B,
A C1-C6 haloalkyl group,
A C1-C6 alkoxy group optionally substituted with a substituent B,
A C1-C6 haloalkoxy group,
A C3-C8 cycloalkoxy group optionally substituted with a substituent B,
A C2-C6 alkenyloxy group optionally substituted with a substituent B,
A C3-C6 alkynyloxy group optionally substituted with a substituent B,
R20C (= O) O- (where R20 is a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group , A C3-C8 cycloalkoxy group, or R21R22N- (wherein R21 and R22 are each independently a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B1, a C1-C6 Represents a haloalkyl group or a C3-C8 cycloalkyl group, or R21 and R22 together with a bonding nitrogen atom form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, a piperidinyl group, a homopiperidinyl group, or an azocanyl group Represents what forms).
Or R23-L2- (wherein, R23 represents an alkyl group or a haloalkyl group of C1 -C6, a C1 -C6, L2 is S, SO, or an SO _2.) Represents;
R3 is
Hydrogen atom,
Halogen atom,
A C1-C6 alkyl group optionally substituted with a substituent C,
A C3-C8 cycloalkyl group optionally substituted with a substituent C,
A C2-C6 alkynyl group optionally substituted with a substituent C,
A C1-C6 alkoxy group optionally substituted with a substituent C,
Or R30-L3- (where R30 has the same meaning as R23, and L3 has the same meaning as L2);
Y represents a phenyl group or a pyridyl group,
In the phenyl group, the substituent D is substituted at the ortho position, the substituent D1 is independently substituted with 0 to 3 as appropriate, and further the substituent D2 is independently substituted with 1 to 4 as appropriate.
In the pyridyl group, the substituent D is substituted at the ortho-position, the substituent D1 is independently optionally substituted with 0 to 2, and the substituent D2 is each independently substituted with 1 to 3 as appropriate;
The substituent D2 is
Cyano group,
A C2-C6 alkenyl group optionally substituted with substituent B,
A C2-C6 alkynyl group optionally substituted with a substituent B,
A C2-C6 alkenyloxy group optionally substituted with a substituent B,
A C3-C6 alkynyloxy group optionally substituted with a substituent B,
A C2-C6 alkoxyalkoxy group,
A C2-C6 cyanoalkoxy group,
A C4-C9 cycloalkylalkoxy group,
A heteroaryl group optionally substituted with a substituent D,
An aryloxy group optionally substituted with a substituent D,
An aralkyloxy group optionally substituted with a substituent D,
R40 (CH2) pU- (where p represents an integer of 1 to 3, and R40 is a 3- to 6-membered ring group containing 1 to 2 oxygen atoms, R41R42N- (where R41 and R42 is each independently a hydrogen atom, a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, or a C3 to C8 cycloalkyl group which may be appropriately substituted with a substituent B1; And R42 represents a group which forms an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, a piperidinyl group, a homopiperidinyl group, or an azocanyl group together with the nitrogen atom to be bonded thereto, or R43-L4- (wherein R43 represents a C1 to C6 alkyl group or a C1 to C6 haloalkyl group; L4 represents S, SO, or SO2), and U represents an acid. Atom or a sulfur atom.),
R41R42N- (where R41 and R42 are as defined above),
R43-L4- (where R43 and L4 are as defined above),
R44C (＝ O) O— (where R44 is a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group, a C1 to C6 An alkoxy group, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group, or R41R42N- (where R41 and R42 have the same meanings as described above);
And R47R48C = N-O- (where R47 and R48 are each independently a hydrogen atom, a C1 to C6 alkyl group optionally substituted with a substituent A, a C1 to C6 haloalkyl group, A C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or R41R42N- (where R41 and R42 are as defined above). The compound according to claim 1, which is at least one member selected from the group consisting of: R1 is
A C1-C6 alkyl group optionally substituted with a substituent A,
Or a C1-C6 haloalkyl group;
R2 is
Halogen atom,
A C1-C6 alkyl group optionally substituted with a substituent B,
A C1-C6 alkoxy group optionally substituted with a substituent B,
Or R23-L2- (wherein, R23 represents an alkyl group or a haloalkyl group of C1 -C6, a C1 -C6, L2 is S, SO, or an SO _2.) Represents;
R3 is
Hydrogen atom,
Halogen atom,
Or a C1-C6 alkyl group optionally substituted with a substituent C;
Y represents a phenyl group,
In the phenyl group, the substituent D is substituted at the ortho-position, the substituent D1 is independently substituted with 0 to 3 as appropriate, and the substituent D2 is independently substituted with 1 to 4 as appropriate. 3. The compound according to 2, or a salt thereof. Equation (2)

Wherein R2 is
Hydroxyl group,
Cyano group,
Nitro group,
Halogen atom,
A C1-C6 alkyl group optionally substituted with a substituent B,
A C1-C6 haloalkyl group,
A C3-C8 cycloalkyl group optionally substituted with a substituent B,
A C2-C6 alkenyl group optionally substituted with substituent B,
A C2-C6 haloalkenyl group,
A C2-C6 alkynyl group optionally substituted with a substituent B,
A C2-C6 haloalkynyl group,
A C1-C6 alkoxy group optionally substituted with a substituent B,
A C1-C6 haloalkoxy group,
A C3-C8 cycloalkoxy group optionally substituted with a substituent B,
A C2-C6 alkenyloxy group optionally substituted with a substituent B,
A C2-C6 haloalkenyloxy group,
A C3-C6 alkynyloxy group optionally substituted with a substituent B,
A C3-C6 haloalkynyloxy group,
R20C (= O)-(where R20 is a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, A C3-C8 cycloalkoxy group, or R21R22N- (wherein R21 and R22 are each independently a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B1, a C1-C6 Represents a haloalkyl group, or a C3-C8 cycloalkyl group, or R21 and R22, together with the nitrogen atom to which they are attached, represent an aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl, homopiperidinyl, or azocanyl group; Represents what is formed.).),
R20C (= O) O- (where R20 has the same meaning as described above),
R21R22N- (where R21 and R22 are as defined above),
R23-L2- (wherein, R23 represents an alkyl group or a haloalkyl group of C1 -C6, a C1 -C6, L2 represents S, SO, or SO _2.),
R24C (= O) N (R25)-(where R24 is a hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1 Represents a haloalkoxy group of C6 to C6, a cycloalkoxy group of C3 to C8, or R21R22N- (where R21 and R22 have the same meanings as described above), and R25 is appropriately substituted with a hydrogen atom or a substituent B1. Represents a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, or a C3 to C8 cycloalkyl group.)
Or a 3- to 6-membered ring group containing 1 to 2 oxygen atoms;
R3 is
Hydrogen atom,
Nitro group,
Halogen 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 C1-C6 alkoxy group optionally substituted with a substituent C,
A C1-C6 haloalkoxy group,
R30-L3- (where R30 has the same meaning as R23, and L3 has the same meaning as L2);
R31R32N- (where R31 and R32 have the same meanings as R21 and R22 described above),
Or R33C (= O)-(where R33 represents a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group);
n represents an integer of 0 to 5 (however, when n is 2 or more, 2 or more R2 represents an independent substituent);
X represents an oxygen atom or a sulfur atom;
Y represents a phenyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, a thienyl group, a thiazolyl group, or an isothiazolyl group;
In the phenyl group, the substituent D is substituted at the ortho position, the substituent D1 is independently substituted with 0 to 3 as appropriate, and further the substituent D2 is independently substituted with 1 to 4 as appropriate.
In the pyridyl group, the pyridazinyl group, the pyrimidinyl group, the pyrazinyl group, or the triazinyl group, the substituent D is substituted at the ortho position, and the substituents D1 are each independently optionally substituted with 0 to 2, and further substituted. Groups D2 are each independently appropriately substituted with 1 to 3,
In the thienyl group, the thiazolyl group, or the isothiazolyl group, the substituent D is substituted at the ortho position, the substituents D1 are each independently optionally substituted with 0 to 1, and the substituents D2 are each independently substituted. Substitute 1-2 as appropriate;
And the substituent B 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, R21R22N- R21 and R22 are as defined above, R23-L2- (where R23 and L2 are as defined above), R26R27R28Si- (where R26, R27 and R28 are each independently represents an alkyl group having C1~C6 _{have.), R26R27R28Si- (CH 2)} s-O- ( wherein, s represents an integer of 1 to 3, R26, R27 and R28 is a as defined above ), R20C (= O)-(where R20 has the same meaning as described above), and a 3- to 6-membered ring group containing 1 to 2 oxygen atoms. That is at least one selected from the group;
The substituent B1 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, R31R32N- (where R31 and R32 are the aforementioned R21 And R22 and R30-L3- (where R30 has the same meaning as R23, and L3 has the same meaning as L2). Species;
Substituent D is
At least one selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, and a C1-C6 haloalkoxy group;
The substituent D1 is
Hydroxyl group, halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, and C3-C8 cycloalkoxy group At least one selected from the group consisting of:
The substituent D2 is
Cyano group,
Nitro group,
A C2-C6 alkenyl group optionally substituted with substituent B,
A C2-C6 haloalkenyl group,
A C2-C6 alkynyl group optionally substituted with a substituent B,
A C2-C6 haloalkynyl group,
A C2-C6 alkenyloxy group optionally substituted with a substituent B,
A C2-C6 haloalkenyloxy group,
A C3-C6 alkynyloxy group optionally substituted with a substituent B,
A C3-C6 haloalkynyloxy group,
A C2-C6 alkoxyalkoxy group,
A C2-C6 cyanoalkoxy group,
A C4-C9 cycloalkylalkoxy group,
An aryl group optionally substituted with a substituent D,
A heteroaryl group optionally substituted with a substituent D,
An aryloxy group optionally substituted with a substituent D,
A heteroaryloxy group optionally substituted with a substituent D,
An aralkyloxy group optionally substituted with a substituent D,
R40 (CH2) pU- (where p represents an integer of 1 to 3, and R40 is a 3- to 6-membered ring group containing 1 to 2 oxygen atoms, R41R42N- (where R41 and R42 has the same meaning as R21 and R22 described above; or R43-L4- (where R43 has the same meaning as R14, and L4 has the same meaning as L1); U represents an oxygen atom or a sulfur atom.),
R41R42N- (where R41 and R42 are as defined above),
R43-L4- (where R43 has the same meaning as R14, and L4 has the same meaning as L1);
R44C (＝ O)-(where R44 is a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group which may be appropriately substituted with a substituent B A group, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group, or R41R42N- (where R41 and R42 have the same meanings as described above),
R44C (= O) O- (where R44 is as defined above),
R45C (＝ O) N (R46)-(where R45 is a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl A group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or R41R42N- (where R41 and R42 have the same meanings as described above); A hydrogen atom, a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, or a C3 to C8 cycloalkyl group which may be appropriately substituted with a substituent A);
R47R48C = N-O- (where R47 and R48 are each independently a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C Represents a C8 cycloalkyl group, a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group, or R41R42N- (where R41 and R42 have the same meanings as described above). .),
And at least one selected from the group consisting of a 3- to 6-membered ring group containing 1 to 2 oxygen atoms. Or a salt thereof.   An agricultural and horticultural pesticide comprising the compound according to claim 1 or a salt thereof as an active ingredient.   An agricultural and horticultural fungicide comprising the compound according to claim 1 or a salt thereof as an active ingredient.   A method for controlling plant diseases, comprising applying the pesticidal composition for agricultural and horticultural use according to claim 5 to plants, plant seeds, or soil where the plants are grown.   A method for controlling plant diseases, comprising applying the agricultural and horticultural fungicide according to claim 6 to a plant, a plant seed, or a soil in which the plant is grown.