JPWO2014065411A1 - Sulfonamide derivatives as pest control agents for agriculture and horticulture - Google Patents

Abstract

A novel sulfonamide compound represented by the following formula [I]. Since the compound exhibits excellent control activity against pests such as pathogens, insects, mites, nematodes and the like that particularly affect agricultural and horticultural plants, it is extremely useful as a new agricultural chemical. <In the case of a) and b), B can be substituted with formyl, halogen, haloalkyl, cyano, nitro, etc.>

Description

  The present invention relates to a novel sulfonamide derivative useful as a pest control agent, in particular, an agricultural and horticultural pest control agent.

  From Patent Documents 1 to 24 and Non-Patent Documents 1 to 11, it is known that various sulfonamide derivatives have pest control activity.

  However, in recent years, due to the development of drug resistance against pest control agents, a decrease in drug efficacy has become a serious problem. For this reason, there is still a need for the development of new compounds to replace conventional sulfonamide compounds having pest control activity. The sulfonamide derivative of the present invention is a novel compound and is not known to have agricultural and horticultural pest control activities.

WO2006 / 097489 WO2007 / 093599 WO2008 / 022937 WO2008 / 062011 Publication WO2008 / 062012 Publication WO2009 / 071448 WO2009 / 101078 WO2009 / 101082 publication WO2009 / 103650 publication WO2009 / 112533 WO2009 / 112523 WO2009 / 124903 Publication WO2009 / 141241 WO2009 / 141274 WO2009 / 144159 US2004 / 87789 WO2009 / 111830 publication WO 2008/25509 WO2006 / 29154 WO2004 / 074238 WO2005 / 80350 Publication WO2009 / 57827 US005663357 Publication WO2012 / 04378 publication WO2010 / 132999 WO2005 / 116209 publication

Synlett, 1996, 521 Journal of Organic Chemistry, 1996, 61, 6906. Journal of Organic Chemistry, 1998, 63, 1761. Zhurnal Organicheskoi Kimii, 1986, 22, 1195. Synlett, 1996, 521. Zhurnal Organicheskoi Kimii, 1982, 18, 2295. Tetrahedron, 1993, 49, 49. Journal of Organic Chemistry, 1993, 58, 7832. Synlett, 2011, (8), 1117. Bioorganic & Medicinal Chemistry, 2005, 13, 4022. Tetrahedron, 2007, 63, 291. Synthesis, 2011, (5), 816. Journal of Chemical Society (C), 1968, 1120.

  An object of the present invention is to provide a novel sulfonamide derivative and an agricultural and horticultural pest control agent comprising the same as an active ingredient.

  As a result of intensive studies to solve the above-mentioned problems, the present inventors have found that a certain sulfonamide derivative as a novel compound has remarkable agricultural and horticultural insecticidal, acaricidal, nematicidal and bactericidal activities. Based on this finding, the present invention has been completed.

  That is, the present invention is as follows.

  The first invention relates to a sulfonamide derivative represented by the following formula [I].

［式中Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^４は、各々水素原子、−Ｃ（Ｏ）ＯＲ、−Ｃ（Ｏ）Ｒ、−Ｒ、−ＯＲ、−ＳＲ、−ＳＯ_２Ｒ、−ＯＣ（Ｏ）Ｒ、−Ｃ（Ｏ）ＮＨＲ、−Ｃ（Ｏ）ＮＲ_２、−ＮＨＳＯ_２Ｒ、−ＮＲＳＯ_２Ｒ、−ＮＨＲ、−ＮＲ_２、−ＮＨＣ（Ｏ）Ｒ、−ＮＲＣ（Ｏ）Ｒ、−ＮＨＣ（Ｏ）ＯＲ、−ＮＲＣ（Ｏ）ＯＲ、−Ｎ（ＯＲ）Ｃ（Ｏ）ＯＲ、−ＮＨＳＯ_２Ｒ、−ＮＲＳＯ_２Ｒ、−ＳＯ_２ＮＨＲ、−ＳＯ_２ＮＲ_２（ここでのＲは、炭素原子数１〜８の直鎖状又は分岐状のアルキル、炭素原子数２〜８の直鎖状又は分岐状のアルケニル、炭素原子数２〜８の直鎖状又は分岐状のアルキニル、炭素原子数３〜８のシクロアルキル又は炭素原子数３〜８のシクロアルケニルである）、−ＳｉＲ^５Ｒ^６Ｒ^７、−ＯＳｉＲ^５Ｒ^６Ｒ^７（Ｒ^５、Ｒ^６、Ｒ^７炭素原子数１〜６の直鎖状又は分岐状のアルキル、フェニルであり２つ若しくは全てが同じ置換基でも全てが異なる置換基でも良い）、ハロアルキル（同一又は異なって、ハロゲン原子数１〜９で置換されている炭素原子数が１〜４の直鎖状又は分岐状のアルキル基）、ハロアルケニル（同一又は異なって、ハロゲン原子数１〜４で置換されている炭素原子数が２〜６の直鎖状又は分岐状のアルケニル基）、ハロアルコキシ（同一又は異なって、ハロゲン原子数１〜９で置換されている炭素原子数が１〜４の直鎖状又は分岐状のアルコキシ基）、アシルアルコキシ（（炭素原子数が１〜８の直鎖状又は分岐状の脂肪族炭化水素基）−ＣＯ−で表される１〜５個のアシル基により置換された炭素原子数１〜３の直鎖状又は分岐状のアルコキシ基）、アシルオキシアルキル（（炭素原子数が１〜８の直鎖状又は分岐状の脂肪族炭化水素基）−ＣＯ−Ｏ−で表される１〜５個のアシルオキシ基により置換された炭素原子数１〜３の直鎖状又は分岐状のアルキル基）、アルキルスルホニルアルキル（炭素原子数が１〜８の直鎖状又は分岐状の１〜５個のアルキルスルホニル基により置換された炭素原子数１〜３の直鎖状又は分岐状のアルキル基）、シロキシアルキル（１〜５個の−ＯＳｉＲ^５Ｒ^６Ｒ^７（Ｒ^５，Ｒ^６，Ｒ^７は炭素原子数１〜６の直鎖状又は分岐状のアルキル、フェニルであり、２つ若しくは全てが同じ置換基でも全てが異なる置換基でもよい）により置換された炭素原子数１〜３の直鎖状又は分岐状のアルキル基）、ヒドロキシアルキル（１〜５個のヒドロキシル基により置換された炭素原子数１〜３の直鎖状又は分岐状のアルキル基）、アルコキシアルキル（炭素原子数が１〜８の直鎖状又は分岐状の１〜５個のアルコキシ基により置換された炭素原子数１〜３の直鎖状又は分岐状のアルキル基）、ハロアルコキシアルキル（同一又は異なって、ハロゲン原子数１〜９で置換されている炭素原子数が１〜４の直鎖状又は分岐状の１〜５個のハロアルコキシ基により置換された炭素原子数１〜３の直鎖状又は分岐状のアルキル基）、アルキルチオアルキル（炭素原子数が１〜８の直鎖状又は分岐状の１〜５個のアルキルチオ基により置換された炭素原子数１〜３の直鎖状又は分岐状のアルキル基）、ジアルコキシアセタール（炭素原子数が１〜８の直鎖状又は分岐状のアルコキシ基がメチル基に２個置換したジアルコキシメチル基）、アルコキシアルコキシ（炭素原子数が１〜８の直鎖状又は分岐状の１〜５個のアルコキシ基により置換された炭素原子数１〜３の直鎖状又は分岐状のアルキル基）、シアノアルキル（１〜５個のシアノ基により置換された炭素原子数１〜３の直鎖状又は分岐状のアルキル基）、ハロゲン、シアノ、ニトロ、アミノ、ヒドロキシ、ペンタハロスルファニル、ベンジル、ベンジルオキシ、フェニル、フェノキシ、ピリジル、オキサゾリル、フリル、チアゾリル、ナフチル、ピリミジニル、チエニル、ベンゾチアゾリル、ベンゾオキサゾリル、ベンゾオキソリル、イミド、ホルミル（−ＣＨＯ）、カルボキシル（−ＣＯＯＨ）又は、Ｒ^１とＲ^２が結合してピリジン環上の炭素原子と共に形成するチオフェン環、ピリジン環、ピロール環、イミダゾール環、ベンゼン環、ナフタレン環、ピリミジン環、フラン環、ピラジン環、ピラゾール環、オキサゾール環を表し、
Ａは、フェニレン、５若しくは６員環のヘテロアレンジイル（ヘテロアレンは１〜３個のＮ、Ｏ、Ｓ原子を環に含み、また、フェニレン、ヘテロアレンジイルのいずれも、−Ｃ（Ｏ）ＯＲ、−Ｃ（Ｏ）Ｒ、−Ｒ、−ＯＲ、−ＳＲ、−ＳＯ_２Ｒ、−ＯＣ（Ｏ）Ｒ、−Ｃ（Ｏ）ＮＨＲ、−Ｃ（Ｏ）ＮＲ_２、−ＮＨＳＯ_２Ｒ、−ＮＲＳＯ_２Ｒ、−ＮＨＲ、−ＮＲ_２、−ＮＨＣ（Ｏ）Ｒ、−ＮＲＣ（Ｏ）Ｒ、−ＮＨＣ（Ｏ）ＯＲ、−ＮＲＣ（Ｏ）ＯＲ、−Ｎ（ＯＲ）Ｃ（Ｏ）ＯＲ、−ＮＨＳＯ_２Ｒ、−ＮＲＳＯ_２Ｒ、−ＳＯ_２ＮＨＲ、−ＳＯ_２ＮＲ_２（ここでのＲは、炭素原子数１〜８の直鎖状又は分岐状のアルキル、炭素原子数２〜８の直鎖状又は分岐状のアルケニル、炭素原子数２〜８の直鎖状又は分岐状のアルキニル又は炭素原子数３〜８のシクロアルキルまたは炭素原子数３〜８のシクロアルケニルである）、−ＳｉＲ^５Ｒ^６Ｒ^７、−ＯＳｉＲ^５Ｒ^６Ｒ^７（Ｒ^５、Ｒ^６、Ｒ^７炭素原子数１〜６の直鎖状又は分岐状のアルキル、フェニルであり２つ若しくは全てが同じ置換基でも全てが異なる置換基でも良い）、ハロアルキル（同一又は異なって、ハロゲン原子数１〜９で置換されている炭素原子数が１〜４の直鎖状又は分岐状のアルキル基）、ハロアルケニル（同一又は異なって、ハロゲン原子数１〜４で置換されている炭素原子数が２〜６の直鎖状又は分岐状のアルケニル基）、ハロアルコキシ（同一又は異なって、ハロゲン原子数１〜９で置換されている炭素原子数が１〜４の直鎖状又は分岐状のアルコキシ基）、アシルアルコキシ（（炭素原子数が１〜８の直鎖状又は分岐状の脂肪族炭化水素基）−ＣＯ−で表される１〜５個のアシル基により置換された炭素原子数１〜３の直鎖状又は分岐状のアルコキシ基）、アシルオキシアルキル（（炭素原子数が１〜８の直鎖状又は分岐状の脂肪族炭化水素基）−ＣＯ−Ｏ−で表される１〜５個のアシルオキシ基により置換された炭素原子数１〜３の直鎖状又は分岐状のアルキル基）、アルキルスルホニルアルキル（炭素原子数が１〜８の直鎖状又は分岐状の１〜５個のアルキルスルホニル基により置換された炭素原子数１〜３の直鎖状又は分岐状のアルキル基）、シロキシアルキル（１〜５個の−ＯＳｉＲ^５Ｒ^６Ｒ^７（Ｒ^５，Ｒ^６，Ｒ^７は炭素原子数１〜６の直鎖状又は分岐状のアルキル、フェニルであり、２つ若しくは全てが同じ置換基でも全てが異なる置換基でもよい）により置換された炭素原子数１〜３の直鎖状又は分岐状のアルキル基）、ヒドロキシアルキル（１〜５個のヒドロキシル基により置換された炭素原子数１〜３の直鎖状又は分岐状のアルキル基）、アルコキシアルキル（炭素原子数が１〜８の直鎖状又は分岐状の１〜５個のアルコキシ基により置換された炭素原子数１〜３の直鎖状又は分岐状のアルキル基）、ハロアルコキシアルキル（同一又は異なって、ハロゲン原子１〜９で置換されている炭素原子数が１〜４の直鎖状又は分岐状の１〜５個のハロアルコキシ基により置換された炭素原子数１〜３の直鎖状又は分岐状のアルキル基）、アルキルチオアルキル（炭素原子数が１〜８の直鎖状又は分岐状の１〜５個のアルキルチオ基により置換された炭素原子数１〜３の直鎖状又は分岐状のアルキル基）、ジアルコキシアセタール（炭素原子数が１〜８の直鎖状又は分岐状のアルコキシ基がメチル基に２個置換したジアルコキシメチル基）、アルコキシアルコキシ（炭素原子数が１〜８の直鎖状又は分岐状の１〜５個のアルコキシ基により置換された炭素原子数１〜３の直鎖状又は分岐状のアルコキシ基）、シアノアルキル（１〜５個のシアノ基により置換された炭素原子数１〜３の直鎖状又は分岐状のアルキル基）、ハロゲン、シアノ、ニトロ、アミノ、ヒドロキシ、ペンタハロスルファニル、ベンジル、ベンジルオキシ、フェニル、フェノキシ、ピリジル、オキサゾリル、フリル、チアゾリル、ナフチル、ピリミジニル、チエニル、ベンゾチアゾリル、ベンゾオキサゾリル、ベンゾオキソリル、イミド、ホルミル（−ＣＨＯ）、カルボキシル（−ＣＯＯＨ）から選択する１ないし４個の置換基で置換されていても良い）を表し、
Ｂは
ａ）フェニル、ベンジル、オキサゾリル、イソオキサゾリル、フリル、ベンゾフリル、イソベンゾフリル、ジヒドロベンゾフリル、チアゾリル、イソチアゾリル、ナフチル、ピリミジニル、ピラジニル、キノキサリル、キナゾリル、ピリジル、キノリル、イソキノリル、ベンゾチアゾリル、ベンゾイソチアゾリル、ピロリル、インドリル、イソインドリル、ベンゾオキサゾリル、ベンゾイソオキサゾリル、チエニル、ベンゾチエニル、イミダゾリル、ベンズイミダゾリル、ピラゾリル、ピリドニル、トリアジニル、トリアゾリル、チアジアゾリル、オキサジアゾリル、テトラゾリル、フェロセニルから成る群より選択される、０〜３個のヘテロ原子を場合によっては含有する単環式もしくは二環式の環、
ｂ）炭素原子数１〜６の直鎖状又は分岐状のアルキル、炭素原子数２〜８の直鎖状又は分岐状のアルケニル、炭素原子数２〜８の直鎖状又は分岐状のアルキニル、炭素原子数３〜８のシクロアルキル又は炭素原子数３〜８のシクロアルケニル、
ｃ）−ＳｉＲ^５Ｒ^６Ｒ^７（Ｒ^５、Ｒ^６、Ｒ^７は炭素原子数１〜６の直鎖状又は分岐状のアルキル、フェニルであり、２つ若しくは全てが同じ置換基でも全てが異なる置換基でもよい）、
ｄ）−Ｃ（Ｏ）ＯＲ、−Ｃ（Ｏ）ＮＨＲ、−Ｃ（Ｏ）ＮＲ_２、−ＳＯ_２ＮＨＲ、−ＳＯ_２ＮＲ_２（ここでのＲは、炭素原子数１〜８の直鎖状又は分岐状のアルキル、炭素原子数２〜８の直鎖状又は分岐状のアルケニル、炭素原子数２〜８の直鎖状又は分岐状のアルキニル、炭素原子数３〜８のシクロアルキルまたは炭素原子数３〜８のシクロアルケニル、ベンジルまたは環状エーテルである）、ハロゲン、ホルミル（−ＣＨＯ）またはカルボキシル（−ＣＯＯＨ）、
ｅ）水素原子
から選択され、ａ）、ｂ）の場合Ｂは−Ｃ（Ｏ）ＯＲ、−Ｃ（Ｏ）Ｒ、−Ｒ、−ＯＲ、−ＳＲ、−ＳＯ_２Ｒ、−ＯＣ（Ｏ）Ｒ、−Ｃ（Ｏ）ＮＨＲ、−Ｃ（Ｏ）ＮＲ_２、−ＮＨＳＯ_２Ｒ、−ＮＲＳＯ_２Ｒ、−ＮＨＲ、−ＮＲ_２、−ＮＨＣ（Ｏ）Ｒ、−ＮＲＣ（Ｏ）Ｒ、−ＮＨＣ（Ｏ）ＯＲ、−ＮＲＣ（Ｏ）ＯＲ、−Ｎ（ＯＲ）Ｃ（Ｏ）ＯＲ、−ＮＨＳＯ_２Ｒ、−ＮＲＳＯ_２Ｒ、＝ＮＯＲ、−ＳＯ_２ＮＨＲ、−ＳＯ_２ＮＲ_２（ここでのＲは、炭素原子数１〜８の直鎖状又は分岐状のアルキル、炭素原子数２〜８の直鎖状又は分岐状のアルケニル、炭素原子数２〜８の直鎖状又は分岐状のアルキニル、炭素原子数３〜８のシクロアルキル、炭素原子数３〜８のシクロアルケニルまたは環状エーテルである）、−ＳｉＲ^５Ｒ^６Ｒ^７、−ＯＳｉＲ^５Ｒ^６Ｒ^７（Ｒ^５、Ｒ^６、Ｒ^７炭素原子数１〜６の直鎖状又は分岐状のアルキル、フェニルであり２つ若しくは全てが同じ置換基でも全てが異なる置換基でも良い）、ハロアルキル（同一又は異なって、ハロゲン原子数１〜９で置換されている炭素原子数が１〜４の直鎖状又は分岐状のアルキル基）、ハロアルケニル（同一又は異なって、ハロゲン原子数１〜４で置換されている炭素原子数が２〜６の直鎖状又は分岐状のアルケニル基）、ハロアルコキシ（同一又は異なって、ハロゲン原子数１〜９で置換されている炭素原子数が１〜４の直鎖状又は分岐状のアルコキシ基）、ハロアルキルチオ（同一又は異なって、ハロゲン原子数１〜９で置換されている炭素原子数が１〜４の直鎖状又は分岐状のアルキルチオ基）、アシルアルコキシ（（炭素原子数が１〜８の直鎖状又は分岐状の脂肪族炭化水素基）−ＣＯ−で表される１〜５個のアシル基により置換された炭素原子数１〜３の直鎖状又は分岐状のアルコキシ基）、アシルオキシアルキル（（炭素原子数が１〜８の直鎖状又は分岐状の脂肪族炭化水素基）−ＣＯ−Ｏ−で表される１〜５個のアシルオキシ基により置換された炭素原子数１〜３の直鎖状又は分岐状のアルキル基）、アルキルスルホニルアルキル（炭素原子数が１〜８の直鎖状又は分岐状の１〜５個のアルキルスルホニル基により置換された炭素原子数１〜３の直鎖状又は分岐状のアルキル基）、シロキシアルキル（１〜５個の−ＯＳｉＲ^５Ｒ^６Ｒ^７（Ｒ^５，Ｒ^６，Ｒ^７は炭素原子数１〜６個の直鎖状又は分岐状のアルキル、フェニルであり、２つ若しくは全てが同じ置換基でも全てが異なる置換基でもよい）により置換された炭素原子数１〜３の直鎖状又は分岐状のアルキル基）、ヒドロキシアルキル（１〜５個のヒドロキシル基により置換された炭素原子数１〜３の直鎖状又は分岐状のアルキル基）、アルコキシアルキル（炭素原子数が１〜８の直鎖状又は分岐状の１〜５個のアルコキシ基により置換された炭素原子数１〜３の直鎖状又は分岐状のアルキル基）、ハロアルコキシアルキル（同一又は異なって、ハロゲン原子数１〜９で置換されている炭素原子数が１〜４の直鎖状又は分岐状の１〜５個のハロアルコキシ基により置換された炭素原子数１〜３の直鎖状又は分岐状のアルキル基）、アルキルチオアルキル（炭素原子数が１〜８の直鎖状又は分岐状の１〜５個のアルキルチオ基により置換された炭素原子数１〜３の直鎖状又は分岐状のアルキル基）、ジアルコキシアセタール（炭素原子数が１〜８の直鎖状又は分岐状のアルコキシ基がメチル基に２個置換したジアルコキシメチル基）、アルコキシアルコキシ（炭素原子数が１〜８の直鎖状又は分岐状の１〜５個のアルコキシ基により置換された炭素原子数１〜３の直鎖状又は分岐状のアルキル基）、シアノアルキル（１〜５個のシアノ基により置換された炭素原子数１〜３の直鎖状又は分岐状のアルキル基）、ハロゲン、シアノ、ニトロ、アミノ、ヒドロキシ、ペンタハロスルファニル、ベンジル、ベンジルオキシ、フェニル、フェノキシ、ピリジル、オキサゾリル、フリル、チアゾリル、ナフチル、ピリミジニル、チエニル、ベンゾチアゾリル、ベンゾオキサゾリル、ベンゾオキソリル、イミド、ホルミル（−ＣＨＯ）、カルボキシル（−ＣＯＯＨ）、オキソ（＝Ｏ）から選択する１ないし７個の置換基で置換されていても良い。］

[Wherein R ¹ , R ² , R ³ , R ⁴ are a hydrogen atom, —C (O) OR, —C (O) R, —R, —OR, —SR, —SO ₂ R, —OC, respectively. (O) R, —C (O) NHR, —C (O) NR ₂ , —NHSO ₂ R, —NRSO ₂ R, —NHR, —NR ₂ , —NHC (O) R, —NRC (O) R , —NHC (O) OR, —NRC (O) OR, —N (OR) C (O) OR, —NHSO ₂ R, —NRSO ₂ R, —SO ₂ NHR, —SO ₂ NR ₂ (where R is linear or branched alkyl having 1 to 8 carbon atoms, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms. , cycloalkyl or cycloalkenyl having 3 to 8 carbon atoms carbon atoms ^{3~8), - SiR 5 R 6} R 7, -OSi ^{5 R 6 R 7 (R 5} , R 6, R 7 having 1 to 6 carbon atoms straight or branched alkyl, two or all phenyl may be all be the same substituent is different substituents) Haloalkyl (same or different, linear or branched alkyl group having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms), haloalkenyl (same or different, 1 halogen atom A linear or branched alkenyl group having 2 to 6 carbon atoms substituted with ˜4, and a haloalkoxy (identical or different, the number of carbon atoms substituted with 1 to 9 halogen atoms is 1 -4 linear or branched alkoxy groups), acylalkoxy ((linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) -CO- 1-5 1 carbon atom substituted by an acyl group of 1 to 3 represented by 1 to 3 linear or branched alkoxy groups), acyloxyalkyl ((linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) -CO-O-. C1-C3 linear or branched alkyl group substituted with 5 acyloxy groups), alkylsulfonylalkyl (C1-C8 linear or branched 1-5 carbon atoms) A linear or branched alkyl group having 1 to 3 carbon atoms substituted with an alkylsulfonyl group, or siloxyalkyl (1 to 5 —OSiR ⁵ R ⁶ R ⁷ (R ⁵ , R ⁶ , R ^7). Is a straight or branched alkyl or phenyl having 1 to 6 carbon atoms, two or all of which may be the same substituent or all different substituents). Chain or branched alkyl group), hydroxy Alkyl (a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 5 hydroxyl groups), alkoxyalkyl (a linear or branched 1 having 1 to 8 carbon atoms) A linear or branched alkyl group having 1 to 3 carbon atoms substituted by -5 alkoxy groups, a haloalkoxyalkyl (identical or different, carbon atoms substituted with 1 to 9 halogen atoms) A linear or branched alkyl group having 1 to 4 carbon atoms substituted with 1 to 4 linear or branched haloalkoxy groups having 1 to 4 carbon atoms, alkylthioalkyl (the number of carbon atoms is 1 to 8 linear or branched alkyl groups having 1 to 3 carbon atoms substituted with 1 to 5 linear or branched alkylthio groups), dialkoxy acetals (having 1 to 5 carbon atoms) 8 linear or branched A dialkoxymethyl group in which an alkoxy group is substituted with two methyl groups), alkoxyalkoxy (a carbon number of 1 to 1 substituted with 1 to 5 linear or branched alkoxy groups having 1 to 8 carbon atoms) 3 linear or branched alkyl groups), cyanoalkyl (C1-C3 linear or branched alkyl groups substituted by 1 to 5 cyano groups), halogen, cyano, nitro , Amino, hydroxy, pentahalosulfanyl, benzyl, benzyloxy, phenyl, phenoxy, pyridyl, oxazolyl, furyl, thiazolyl, naphthyl, pyrimidinyl, thienyl, benzothiazolyl, benzoxazolyl, benzooxolyl, imide, formyl (-CHO), carboxyl (-COOH) or a carbon atom on the pyridine ring by bonding ^{R 1} and ^{R 2} It represents a thiophene ring which together form a pyridine ring, a pyrrole ring, an imidazole ring, a benzene ring, a naphthalene ring, a pyrimidine ring, a furan ring, a pyrazine ring, a pyrazole ring, an oxazole ring,
A is phenylene, 5- or 6-membered heteroarrangeyl (heteroarene contains 1 to 3 N, O, and S atoms in the ring, and both phenylene and heteroarrangeyl are -C (O) OR _{, -C (O) R, -R} , -OR, -SR, -SO 2 R, -OC (O) R, -C (O) NHR, -C (O) NR 2, -NHSO 2 R, - _{NRSO 2 R, -NHR, -NR 2} , -NHC (O) R, -NRC (O) R, -NHC (O) OR, -NRC (O) OR, -N (OR) C (O) OR, —NHSO ₂ R, —NRSO ₂ R, —SO ₂ NHR, —SO ₂ NR ₂ (wherein R is linear or branched alkyl having 1 to 8 carbon atoms, and having 2 to 8 carbon atoms) Linear or branched alkenyl, linear or branched alkynyl having 2 to 8 carbon atoms or carbon atom Number 3-8 cycloalkyl or cycloalkenyl having 3 to 8 carbon atoms ^{of), - SiR 5 R 6 R} 7, -OSiR 5 R 6 R 7 (R 5, R 6, R 7 carbon atoms 1 6 linear or branched alkyl, phenyl, two or all of which may be the same substituent or all different substituents, haloalkyl (identical or different, substituted with 1 to 9 halogen atoms) Straight chain or branched alkyl group having 1 to 4 carbon atoms), haloalkenyl (same or different, straight chain having 2 to 6 carbon atoms substituted with 1 to 4 halogen atoms, or Branched alkenyl group), haloalkoxy (same or different, linear or branched alkoxy group having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms), acylalkoxy ((carbon Number of atoms -8 linear or branched aliphatic hydrocarbon group) linear or branched alkoxy group having 1 to 5 carbon atoms substituted by 1 to 5 acyl groups represented by -CO-. ), Acyloxyalkyl ((a linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms)-the number of carbon atoms substituted by 1 to 5 acyloxy groups represented by -CO-O- 1 to 3 linear or branched alkyl groups), alkylsulfonylalkyl (1 to 1 carbon atoms substituted with 1 to 5 linear or branched alkylsulfonyl groups having 1 to 8 carbon atoms) To 3 linear or branched alkyl groups), siloxyalkyl (1 to 5 —OSiR ⁵ R ⁶ R ⁷ (R ⁵ , R ⁶ and R ⁷ are linear or 1 to 6 carbon atoms) Branched alkyl, phenyl, two or all have the same substituents However, all may be different substituents), a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1), hydroxyalkyl (1 to 1 carbon atoms substituted by 1 to 5 hydroxyl groups) 3 straight-chain or branched alkyl groups), alkoxyalkyl (1-3 carbon atoms directly substituted with 1-5 straight-chain or branched alkoxy groups having 1 to 8 carbon atoms) Linear or branched alkyl group), haloalkoxyalkyl (same or different, linear or branched 1 to 5 halo having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms) A linear or branched alkyl group having 1 to 3 carbon atoms substituted with an alkoxy group), an alkylthioalkyl (a linear or branched alkyl group having 1 to 8 carbon atoms having 1 to 8 carbon atoms) Substituted carbon field A linear or branched alkyl group of 1 to 3), dialkoxyacetal (a dialkoxymethyl group in which a linear or branched alkoxy group having 1 to 8 carbon atoms is substituted with two methyl groups) , Alkoxyalkoxy (a linear or branched alkoxy group having 1 to 3 carbon atoms substituted by a linear or branched alkoxy group having 1 to 8 carbon atoms), cyanoalkyl (C1-C3 linear or branched alkyl group substituted with 1 to 5 cyano groups), halogen, cyano, nitro, amino, hydroxy, pentahalosulfanyl, benzyl, benzyloxy, phenyl , Phenoxy, pyridyl, oxazolyl, furyl, thiazolyl, naphthyl, pyrimidinyl, thienyl, benzothiazolyl, benzoxazolyl, benzooxolyl Imides, represent formyl (-CHO), a carboxyl to 1 to choose from (-COOH) may be substituted with four substituents),
B is a) phenyl, benzyl, oxazolyl, isoxazolyl, furyl, benzofuryl, isobenzofuryl, dihydrobenzofuryl, thiazolyl, isothiazolyl, naphthyl, pyrimidinyl, pyrazinyl, quinoxalyl, quinazolyl, pyridyl, quinolyl, isoquinolyl, benzothiazolyl, benzoisothiazolyl , Pyrrolyl, indolyl, isoindolyl, benzoxazolyl, benzoisoxazolyl, thienyl, benzothienyl, imidazolyl, benzimidazolyl, pyrazolyl, pyridonyl, triazinyl, triazolyl, thiadiazolyl, oxadiazolyl, tetrazolyl, ferrocenyl A monocyclic or bicyclic ring optionally containing 0 to 3 heteroatoms,
b) linear or branched alkyl having 1 to 6 carbon atoms, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, Cycloalkyl having 3 to 8 carbon atoms or cycloalkenyl having 3 to 8 carbon atoms,
c) —SiR ⁵ R ⁶ R ⁷ (R ⁵ , R ⁶ , R ⁷ are linear or branched alkyl or phenyl having 1 to 6 carbon atoms, and even if two or all are the same substituents, all Different substituents may be used),
d) -C (O) OR, -C (O) NHR, -C (O) NR 2, -SO 2 NHR, R in _-SO 2 NR ₂ (where linear 1 to 8 carbon atoms Or branched alkyl, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, cycloalkyl or carbon having 3 to 8 carbon atoms C 3 -C 8 cycloalkenyl, benzyl or cyclic ether), halogen, formyl (—CHO) or carboxyl (—COOH),
e) selected from hydrogen atoms, and in the case of a) and b) B is —C (O) OR, —C (O) R, —R, —OR, —SR, —SO ₂ R, —OC (O) R, —C (O) NHR, —C (O) NR ₂ , —NHSO ₂ R, —NRSO ₂ R, —NHR, —NR ₂ , —NHC (O) R, —NRC (O) R, —NHC _{(O) OR, -NRC (O} ) OR, -N (OR) C (O) OR, -NHSO 2 R, -NRSO 2 R, = NOR, -SO 2 NHR, -SO 2 NR 2 ( here R is linear or branched alkyl having 1 to 8 carbon atoms, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms. A cycloalkyl having 3 to 8 carbon atoms, a cycloalkenyl having 3 to 8 carbon atoms or a cyclic ether), -SiR ⁵ R ⁶ R ⁷ , —OSiR ⁵ R ⁶ R ⁷ (R ⁵ , R ⁶ , R ⁷ linear or branched alkyl having 1 to 6 carbon atoms, phenyl, two or all of which are the same substituents, all May be different substituents), haloalkyl (same or different, linear or branched alkyl group having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms), haloalkenyl (identical or Differently, a linear or branched alkenyl group having 2 to 6 carbon atoms substituted with 1 to 4 halogen atoms, haloalkoxy (identical or different, substituted with 1 to 9 halogen atoms) Straight chain or branched alkoxy group having 1 to 4 carbon atoms), haloalkylthio (same or different, straight chain having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms) Or branched alkyl O group), acylalkoxy ((linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) -CO-, the number of carbon atoms substituted by 1 to 5 acyl groups 1 to 3 represented by 1 to 3 linear or branched alkoxy groups) and acyloxyalkyl ((linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) -CO-O-. A linear or branched alkyl group having 1 to 3 carbon atoms substituted by 5 acyloxy groups, alkylsulfonylalkyl (a linear or branched 1 to 5 carbon atom having 1 to 8 carbon atoms) A linear or branched alkyl group having 1 to 3 carbon atoms substituted with 1 alkylsulfonyl group), siloxyalkyl (1 to 5 —OSiR ⁵ R ⁶ R ⁷ (R ⁵ , R ⁶ , R) ⁷ is a linear or branched alkyl having 1 to 6 carbon atoms, A linear or branched alkyl group having 1 to 3 carbon atoms, which is substituted by phenyl or two or all may be the same substituent or all different substituents), hydroxyalkyl (1 to 5 A linear or branched alkyl group having 1 to 3 carbon atoms substituted by a hydroxyl group, alkoxyalkyl (a linear or branched alkoxy group having 1 to 8 carbon atoms) A linear or branched alkyl group having 1 to 3 carbon atoms substituted by haloalkoxyalkyl (identical or different, and having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms) A linear or branched alkyl group having 1 to 3 carbon atoms substituted by a linear or branched 1 to 5 haloalkoxy group, alkylthioalkyl (a linear chain having 1 to 8 carbon atoms) Or branched A linear or branched alkyl group having 1 to 3 carbon atoms substituted with 5 alkylthio groups), a dialkoxyacetal (a linear or branched alkoxy group having 1 to 8 carbon atoms). A dialkoxymethyl group substituted with two methyl groups), an alkoxyalkoxy (a straight chain having 1 to 8 carbon atoms and a straight chain or branched chain having 1 to 5 carbon atoms substituted with 1 to 3 carbon atoms) A chain or branched alkyl group), cyanoalkyl (a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 5 cyano groups), halogen, cyano, nitro, amino, Hydroxy, pentahalosulfanyl, benzyl, benzyloxy, phenyl, phenoxy, pyridyl, oxazolyl, furyl, thiazolyl, naphthyl, pyrimidinyl, thienyl, benzothia , Benzoxazolyl, Benzookisoriru, imide, formyl (-CHO), a carboxyl (-COOH), an oxo (= O) may be substituted with 1 to select to 7 substituents from. ]

  The second invention is a method for producing a sulfonamide derivative represented by the formula [I].

  Furthermore, the third invention is a pest control agent comprising one or more sulfonamide derivatives represented by the formula [I] as an active ingredient.

  The novel sulfonamide derivative of the present invention represented by the formula [I] has an excellent control effect against pests, particularly agricultural and horticultural pests.

  Hereinafter, the present invention will be described in detail.

  In addition to the sulfonamide derivative represented by the formula [I], the sulfonamide derivative in the present invention includes a salt (sodium salt, potassium salt, magnesium salt, calcium salt, aluminum salt, etc.), hydrate, Also included are solvates, crystalline polymorphic substances, and N-oxides of sulfonamide derivatives of formula [I]. Furthermore, all possible stereoisomers or optical isomers present in the compound of the present invention, and a mixture containing two or more kinds of isomers in any ratio are also represented by the compound of the present invention (sulfonamide derivative represented by the formula [I]). ).

R ¹ , R ² , R ³ , R ⁴ , A and B represented by the compound [I] are as follows.

R ¹ is a hydrogen atom, —C (O) OR, —C (O) R, —R, —OR, —SR, —SO ₂ R, —OC (O) R, —C (O) NHR, — C (O) NR ₂ , —NHSO ₂ R, —NRSO ₂ R, —NHR, —NR ₂ , —NHC (O) R, —NRC (O) R, —NHC (O) OR, —NRC (O) OR, —N (OR) C (O) OR, —NHSO ₂ R, —NRSO ₂ R, —SO ₂ NHR, —SO ₂ NR ₂ (where R is a straight chain having 1 to 8 carbon atoms) Or branched alkyl, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, or cycloalkyl or carbon atom having 3 to 8 carbon atoms number 3-8 cycloalkenyl ^{of), - SiR 5 R 6 R} 7, -OSiR 5 R 6 R 7 (R 5, R 6 , R ⁷ is linear or branched alkyl having 1 to 6 carbon atoms, phenyl, two or all of which may be the same or different, and haloalkyl (identical or different, halogen atoms A linear or branched alkyl group having 1 to 4 carbon atoms substituted with 1 to 9 and haloalkenyl (identical or different, and substituted with 1 to 4 halogen atoms) Is a linear or branched alkenyl group having 2 to 6), haloalkoxy (same or different, linear or branched having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms) Alkoxy group), acylalkoxy ((linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) —the number of carbon atoms substituted by 1 to 5 acyl groups represented by —CO—. 1-3 linear or branched a Coxy group), acyloxyalkyl ((a linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) -CO-O-- substituted with 1 to 5 acyloxy groups Straight or branched alkyl group having 1 to 3 atoms), alkylsulfonylalkyl (carbon atom substituted with 1 to 5 linear or branched alkylsulfonyl groups having 1 to 8 carbon atoms) A linear or branched alkyl group of 1 to 3), siloxyalkyl (1 to 5 —OSiR ⁵ R ⁶ R ⁷ (R ⁵ , R ⁶ and R ⁷ are each a straight chain having 1 to 6 carbon atoms) A linear or branched alkyl group having 1 to 3 carbon atoms substituted by chain or branched alkyl or phenyl, and two or all of them may be the same substituent or all different substituents) , Hydroxyalkyl (1-5 hydrides A linear or branched alkyl group having 1 to 3 carbon atoms substituted by a xyl group, alkoxyalkyl (a linear or branched 1 to 5 alkoxy group having 1 to 8 carbon atoms) Straight or branched alkyl group having 1 to 3 carbon atoms), haloalkoxyalkyl (same or different, straight chain having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms) A linear or branched alkyl group having 1 to 3 carbon atoms substituted by a linear or branched 1 to 5 haloalkoxy group, alkylthioalkyl (a linear chain having 1 to 8 carbon atoms) Or a linear or branched alkyl group having 1 to 3 carbon atoms substituted with 1 to 5 branched alkylthio groups), dialkoxy acetal (linear or branched having 1 to 8 carbon atoms) -Like alkoxy group to methyl group 1-substituted dialkoxymethyl group), alkoxyalkoxy (a linear or branched carbon having 1 to 3 carbon atoms substituted by 1 to 5 linear or branched alkoxy groups having 1 to 8 carbon atoms) -Like alkoxy group), cyanoalkyl (C1-C3 linear or branched alkyl group substituted by 1 to 5 cyano groups), halogen, cyano, nitro, amino, hydroxy, pentahalo Sulfanyl, benzyl, benzyloxy, phenyl, phenoxy, pyridyl, oxazolyl, furyl, thiazolyl, naphthyl, pyrimidinyl, thienyl, benzothiazolyl, benzoxazolyl, benzooxolyl, imide, formyl (—CHO), carboxyl (—COOH) or R ^{thiophene 1} and R ² form together with the carbon atoms on the binding to the pyridine ring Represents a pyridine ring, a pyrrole ring, an imidazole ring, a benzene ring, a naphthalene ring, a pyrimidine ring, a furan ring, a pyrazine ring, a pyrazole ring, an oxazole ring.

R ² , R ³ and R ⁴ are each a hydrogen atom, —C (O) OR, —C (O) R, —R, —OR, —SR, —SO ₂ R, —OC (O) R, — _{C (O) NHR, -C (} O) NR 2, -NHSO 2 R, -NRSO 2 R, -NHR, -NR 2, -NHC (O) R, -NRC (O) R, -NHC (O) OR, —NRC (O) OR, —N (OR) C (O) OR, —NHSO ₂ R, —NRSO ₂ R, —SO ₂ NHR, —SO ₂ NR ₂ (where R is the number of carbon atoms) 1-8 linear or branched alkyl, C2-C8 linear or branched alkenyl, C2-C8 linear or branched alkynyl, or C3-C3 8 cycloalkyl or C 3-8 cycloalkenyl), —SiR ⁵ R ⁶ R ⁷ , —OSiR ⁵ R ^6. R ⁷ (R ⁵ , R ⁶ , R ⁷ linear or branched alkyl having 1 to 6 carbon atoms, phenyl, and two or all may be the same or all different substituents), haloalkyl ( Linear or branched alkyl groups having 1 to 4 carbon atoms, which are the same or different and substituted with 1 to 9 halogen atoms, haloalkenyl (identical or different, with 1 to 4 halogen atoms) Linear or branched alkenyl groups having 2 to 6 carbon atoms), haloalkoxy (identical or different, and having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms) Linear or branched alkoxy group), acylalkoxy ((linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) -CO- 1-5 acyl groups Straight from 1 to 3 carbon atoms substituted by Or branched alkoxy groups), acyloxyalkyl ((linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) -CO-O- 1-5 acyloxy groups A linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1), alkylsulfonylalkyl (a linear or branched alkylsulfonyl group having 1 to 8 carbon atoms). A substituted or straight chain or branched alkyl group having 1 to 3 carbon atoms), siloxyalkyl (1 to 5 —OSiR ⁵ R ⁶ R ⁷ (R ⁵ , R ⁶ and R ⁷ are each 1 carbon atom) A linear or branched alkyl group of 1 to 6 carbon atoms substituted by -6 linear or branched alkyls or phenyls, two or all of which may be the same or different. Alkyl group), hydroxyalkyl A linear or branched alkyl group having 1 to 3 carbon atoms substituted with 1 to 5 hydroxyl groups, alkoxyalkyl (a linear or branched 1 to 5 carbon atom having 1 to 8 carbon atoms) Linear or branched alkyl group having 1 to 3 carbon atoms substituted by one alkoxy group), haloalkoxyalkyl (identical or different, the number of carbon atoms substituted with 1 to 9 halogen atoms is 1 to 4 linear or branched 1 to 5 haloalkoxy groups substituted by 1 to 3 carbon atoms, a linear or branched alkyl group having 1 to 3 carbon atoms, alkylthioalkyl (1 to 1 carbon atoms) 8 linear or branched alkyl groups having 1 to 3 carbon atoms substituted by 1 to 5 linear or branched alkylthio groups), dialkoxyacetals (having 1 to 8 carbon atoms) Linear or branched alkoxy Dialkoxymethyl group substituted with 2 methyl groups), alkoxyalkoxy (1-3 carbon atoms substituted with 1 to 5 linear or branched alkoxy groups having 1 to 8 carbon atoms) Linear or branched alkoxy group), cyanoalkyl (C1-C3 linear or branched alkyl group substituted with 1 to 5 cyano groups), halogen, cyano, nitro, amino , Hydroxy, pentahalosulfanyl, benzyl, benzyloxy, phenyl, phenoxy, pyridyl, oxazolyl, furyl, thiazolyl, naphthyl, pyrimidinyl, thienyl, benzothiazolyl, benzoxazolyl, benzooxolyl, imide, formyl (-CHO), carboxyl (- COOH).

A is phenylene, 5- or 6-membered heteroarrangeyl (heteroarene contains 1 to 3 N, O, and S atoms in the ring, and both phenylene and heteroarrangeyl are -C (O) OR _{, -C (O) R, -R} , -OR, -SR, -SO 2 R, -OC (O) R, -C (O) NHR, -C (O) NR 2, -NHSO 2 R, - _{NRSO 2 R, -NHR, -NR 2} , -NHC (O) R, -NRC (O) R, -NHC (O) OR, -NRC (O) OR, -N (OR) C (O) OR, —NHSO ₂ R, —NRSO ₂ R, —SO ₂ NHR, —SO ₂ NR ₂ (wherein R is linear or branched alkyl having 1 to 8 carbon atoms, and having 2 to 8 carbon atoms) Linear or branched alkenyl, linear or branched alkynyl having 2 to 8 carbon atoms, or carbon atom 3-8 cycloalkyl or cycloalkenyl having 3 to 8 carbon atoms ^{of), - SiR 5 R 6 R} 7, -OSiR 5 R 6 R 7 (R 5, R 6, R 7 C 1 -C 6 Linear or branched alkyl, phenyl, two or all of which may be the same or different, and haloalkyl (identical or different, substituted with 1 to 9 halogen atoms) Linear or branched alkyl group having 1 to 4 atoms), haloalkenyl (same or different, linear or branched having 2 to 6 carbon atoms substituted with 1 to 4 halogen atoms) Alkenyl group), haloalkoxy (same or different, linear or branched alkoxy group having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms), acylalkoxy ((carbon atoms) Number is 1 -8 linear or branched aliphatic hydrocarbon group) linear or branched alkoxy group having 1 to 5 carbon atoms substituted by 1 to 5 acyl groups represented by -CO-. ), Acyloxyalkyl ((a linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms)-the number of carbon atoms substituted by 1 to 5 acyloxy groups represented by -CO-O- 1 to 3 linear or branched alkyl groups), alkylsulfonylalkyl (1 to 1 carbon atoms substituted with 1 to 5 linear or branched alkylsulfonyl groups having 1 to 8 carbon atoms) To 3 linear or branched alkyl groups), siloxyalkyl (1 to 5 —OSiR ⁵ R ⁶ R ⁷ (R ⁵ , R ⁶ and R ⁷ are linear with 1 to 6 carbon atoms) Or branched alkyl, phenyl, two or all substituted the same However, all may be different substituents), a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1), hydroxyalkyl (1 to 1 carbon atoms substituted by 1 to 5 hydroxyl groups) 3 straight-chain or branched alkyl groups), alkoxyalkyl (1-3 carbon atoms directly substituted with 1-5 straight-chain or branched alkoxy groups having 1 to 8 carbon atoms) Linear or branched alkyl group), haloalkoxyalkyl (same or different, linear or branched 1-5 carbon atoms having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms) C1-C3 linear or branched alkyl group substituted by haloalkoxy group), alkylthioalkyl (C1-C8 linear or branched alkylthio group having 1 to 5 carbon atoms) Carbon substituted by Straight-chain or branched alkyl group having 1 to 3 atoms), dialkoxyacetal (dialkoxymethyl group in which a straight-chain or branched alkoxy group having 1 to 8 carbon atoms is substituted with two methyl groups) ), Alkoxyalkoxy (a linear or branched alkoxy group having 1 to 3 carbon atoms substituted with a linear or branched alkoxy group having 1 to 8 carbon atoms), cyano Alkyl (a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 5 cyano groups), halogen, cyano, nitro, amino, hydroxy, pentahalosulfanyl, benzyl, benzyloxy, Phenyl, phenoxy, pyridyl, oxazolyl, furyl, thiazolyl, naphthyl, pyrimidinyl, thienyl, benzothiazolyl, benzoxazolyl, benzooxoly Represents imido, formyl (-CHO), a carboxyl to 1 to choose from (-COOH) may be substituted with 4 substituents).

B is selected from any of the following a) to e).
a) Phenyl, benzyl, oxazolyl, isoxazolyl, furyl, benzofuryl, isobenzofuryl, dihydrobenzofuryl, thiazolyl, isothiazolyl, naphthyl, pyrimidinyl, pyrazinyl, quinoxalyl, quinazolyl, pyridyl, quinolyl, isoquinolyl, benzothiazolyl, benzoisothiazolyl, pyrrolyl , Indolyl, isoindolyl, benzoxazolyl, benzoisoxazolyl, thienyl, benzothienyl, imidazolyl, benzimidazolyl, pyrazolyl, pyridonyl, triazinyl, triazolyl, thiadiazolyl, oxadiazolyl, tetrazolyl, ferrocenyl, 0 A monocyclic or bicyclic ring optionally containing ˜3 heteroatoms.
b) linear or branched alkyl having 1 to 6 carbon atoms, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, C3-C8 linear or branched cycloalkyl or C3-C8 cycloalkenyl.
c) —SiR ⁵ R ⁶ R ⁷ (R ⁵ , R ⁶ , R ⁷ are linear or branched alkyl or phenyl having 1 to 6 carbon atoms, and even if two or all are the same substituents, all May be different substituents).
d) -C (O) OR, -C (O) NHR, -C (O) NR 2, -SO 2 NHR, R in _-SO 2 NR ₂ (where linear 1 to 8 carbon atoms Or branched alkyl, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, cycloalkyl or carbon having 3 to 8 carbon atoms C 3 -C 8 cycloalkenyl, benzyl or cyclic ether), halogen, formyl (—CHO) or carboxyl (—COOH).
e) A hydrogen atom.

In the case of a) or b), B represents —C (O) OR, —C (O) R, —R, —OR, —SR, —SO ₂ R, —OC (O) R, —C (O _{) NHR, -C (O) NR} 2, -NHSO 2 R, -NRSO 2 R, -NHR, -NR 2, -NHC (O) R, -NRC (O) R, -NHC (O) OR, - NRC (O) OR, —N (OR) C (O) OR, —NHSO ₂ R, —NRSO ₂ R, ═NOR, —SO ₂ NHR, —SO ₂ NR ₂ (where R is the number of carbon atoms 1-8 linear or branched alkyl, C2-C8 linear or branched alkenyl, C2-C8 linear or branched alkynyl, or C3-C3 8 cycloalkyl, cycloalkenyl, or cyclic ethers having a carbon number of ^{3~8), - SiR 5 R 6} R 7, ^{OSiR 5 R 6 R 7 (R} 5, R 6, R 7 having 1 to 6 carbon atoms straight or branched alkyl, two or all phenyl may be all be the same substituent is different substituents ), Haloalkyl (same or different, linear or branched alkyl group having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms), haloalkenyl (same or different, halogen atoms A linear or branched alkenyl group having 2 to 6 carbon atoms substituted with 1 to 4), haloalkoxy (same or different, the number of carbon atoms substituted with 1 to 9 halogen atoms is 1 to 4 linear or branched alkoxy groups), haloalkylthio (same or different, linear or branched alkylthio having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms) Group), reed A straight chain having 1 to 3 carbon atoms substituted with 1 to 5 acyl groups represented by alkoxy ((linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) -CO-) Chain or branched alkoxy group), acyloxyalkyl ((linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) -CO-O- 1-5 acyloxy C1-C3 linear or branched alkyl group substituted by a group), alkylsulfonylalkyl (C1-C8 linear or branched alkylsulfonyl group having 1 to 8 carbon atoms) A linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1), siloxyalkyl (1 to 5 —OSiR ⁵ R ⁶ R ⁷ (R ⁵ , R ⁶ and R ⁷ are the number of carbon atoms) 1-6 linear or branched alkyl, phenyl, A linear or branched alkyl group having 1 to 3 carbon atoms substituted by 2 or all may be the same substituent or all different substituents), hydroxyalkyl (by 1 to 5 hydroxyl groups) Substituted by a linear or branched alkyl group having 1 to 3 carbon atoms, alkoxyalkyl (a linear or branched alkoxy group having 1 to 8 carbon atoms) A linear or branched alkyl group having 1 to 3 carbon atoms), a haloalkoxyalkyl (same or different, linear or substituted with 1 to 9 halogen atoms or 1 to 4 carbon atoms) A linear or branched alkyl group having 1 to 3 carbon atoms substituted by a branched 1 to 5 haloalkoxy group), alkylthioalkyl (linear or branched having 1 to 8 carbon atoms) 1-5 Archi A linear or branched alkyl group having 1 to 3 carbon atoms substituted with a thio group) or a dialkoxyacetal (a linear or branched alkoxy group having 1 to 8 carbon atoms in the methyl group) 1-substituted dialkoxymethyl group), alkoxyalkoxy (a linear or branched carbon having 1 to 3 carbon atoms substituted by 1 to 5 linear or branched alkoxy groups having 1 to 8 carbon atoms) -Like alkoxy group), cyanoalkyl (C1-C3 linear or branched alkyl group substituted by cyano group), halogen, cyano, nitro, amino, hydroxy, pentahalosulfanyl, benzyl, benzyl Oxy, phenyl, phenoxy, pyridyl, oxazolyl, furyl, thiazolyl, naphthyl, pyrimidinyl, thienyl, benzothiazolyl, benzoxazolyl , Benzookisoriru, imide, formyl (-CHO), a carboxyl (-COOH), an oxo (= O) may be substituted with 1 to select to 7 substituents from.

R ¹ includes a hydrogen atom, —C (O) OR, —C (O) R, —R, —OR, —SR, —SO ₂ R, —OC (O) R, —C (O) NHR, _{-C (O) NR 2, -NHSO} 2 R, -NRSO 2 R, -NHR, -NR 2, -NHC (O) R, -NRC (O) R, -NHC (O) OR, -NRC (O ) OR, —N (OR) C (O) OR, —NHSO ₂ R, —NRSO ₂ R, —SO ₂ NHR, —SO ₂ NR ₂ (where R is a straight chain having 1 to 8 carbon atoms) Or branched alkyl, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, cycloalkyl or carbon having 3 to 8 carbon atoms C 3 -C 8 cycloalkenyl), -SiR ⁵ R ⁶ R ⁷ , -OSiR ⁵ R ⁶ R ⁷ (R ⁵ , R ⁶ and R ⁷ are linear or branched alkyl having 1 to 6 carbon atoms, phenyl, two or all of which may be the same or different, and haloalkyl (identical or different) A linear or branched alkyl group having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms, or a haloalkenyl (identical or different, substituted with 1 to 4 halogen atoms) Straight chain or branched alkenyl group having 2 to 6 carbon atoms), haloalkoxy (same or different, straight chain having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms, or Branched alkoxy group), acylalkoxy ((linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) substituted with 1 to 5 acyl groups represented by -CO- Linear or branched having 1 to 3 carbon atoms Substituted with 1 to 5 acyloxy groups represented by -CO-O- (a linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms). A linear or branched alkyl group having 1 to 3 carbon atoms), alkylsulfonylalkyl (a linear or branched 1 to 5 alkylsulfonyl group having 1 to 8 carbon atoms). A linear or branched alkyl group having 1 to 3 carbon atoms), siloxyalkyl (1 to 5 —OSiR ⁵ R ⁶ R ⁷ (R ⁵ , R ⁶ and R ⁷ are each having 1 to 6 carbon atoms) A linear or branched alkyl group having 1 to 3 carbon atoms substituted by linear or branched alkyl or phenyl, and two or all of them may be the same substituent or all different substituents) ), Hydroxyalkyl (1-5) A linear or branched alkyl group having 1 to 3 carbon atoms substituted with a hydroxyl group), an alkoxyalkyl (a linear or branched 1 to 5 alkoxy group having 1 to 8 carbon atoms) Straight or branched alkyl group having 1 to 3 carbon atoms), haloalkoxyalkyl (same or different, straight chain having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms) A linear or branched alkyl group having 1 to 3 carbon atoms substituted by a linear or branched 1 to 5 haloalkoxy group, alkylthioalkyl (a linear chain having 1 to 8 carbon atoms) Or a linear or branched alkyl group having 1 to 3 carbon atoms substituted with 1 to 5 branched alkylthio groups), dialkoxy acetal (linear or branched having 1 to 8 carbon atoms) -Like alkoxy group is methyl A dialkoxymethyl group substituted by 2 groups), alkoxyalkoxy (a linear chain having 1 to 8 carbon atoms and a straight chain having 1 to 3 carbon atoms substituted by a linear or branched 1 to 5 alkoxy group) Or branched alkoxy group), cyanoalkyl (C1-C3 linear or branched alkyl group substituted by 1 to 5 cyano groups), halogen, cyano, nitro, amino, hydroxy , Pentahalosulfanyl, benzyl, benzyloxy, phenyl, phenoxy, pyridyl, oxazolyl, furyl, thiazolyl, naphthyl, pyrimidinyl, thienyl, benzothiazolyl, benzoxazolyl, benzooxolyl, imide, formyl (—CHO), carboxyl (—COOH) A hydrogen atom, alkyl (eg, methyl group, ethyl , N-propyl group, isopropyl group), alkoxy (for example, methoxy group, ethoxy group, n-propoxy group, isopropoxy group), halogen (for example, fluorine atom, chlorine atom, bromine atom), cyano, haloalkyl (for example, Monofluoromethyl group, difluoromethyl group, trifluoromethyl group, heptafluoroisopropyl group), cyanoalkyl (for example, cyanomethyl group, cyanoethyl group), haloalkoxy (for example, monofluoromethoxy group, difluoromethoxy group, trifluoromethoxy group) ) Is preferred.

Examples of the ring R ¹ to form together with the carbon atoms on the pyridine ring bonded to R ^2, thiophene ring, pyridine ring, pyrrole ring, an imidazole ring, a benzene ring, a naphthalene ring, a pyrimidine ring, a furan ring, a pyrazine ring, a pyrazole Although a ring and an oxazole ring can be mentioned, a benzene ring is preferable.

R ² , R ³ and R ⁴ are each a hydrogen atom, —C (O) OR, —C (O) R, —R, —OR, —SR, —SO ₂ R, —OC (O) R, _{-C (O) NHR, -C (} O) NR 2, -NHSO 2 R, -NRSO 2 R, -NHR, -NR 2, -NHC (O) R, -NRC (O) R, -NHC (O ) OR, —NRC (O) OR, —N (OR) C (O) OR, —NHSO ₂ R, —NRSO ₂ R, —SO ₂ NHR, —SO ₂ NR ₂ (where R is a carbon atom) Linear or branched alkyl having 1 to 8 carbon atoms, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, or 3 carbon atoms 8 of cycloalkyl or cycloalkenyl carbon atoms ^{3~8), - SiR 5 R 6} R 7, -OSiR ^{R 6 R 7 (R 5,} R 6, R 7 having 1 to 6 carbon atoms straight or branched alkyl, two or all phenyl may be all be the same substituent is different substituents), Haloalkyl (same or different, linear or branched alkyl group having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms), haloalkenyl (same or different, halogen atoms 1 to A linear or branched alkenyl group having 2 to 6 carbon atoms substituted with 4, haloalkoxy (identical or different, and having 1 to 9 carbon atoms substituted with 1 to 9 halogen atoms). 4 linear or branched alkoxy groups), acylalkoxy ((linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) -CO- 1 to 1 carbon atoms substituted by an acyl group Linear or branched alkoxy group), acyloxyalkyl ((linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) -CO-O- 1-5 A linear or branched alkyl group having 1 to 3 carbon atoms substituted by an acyloxy group of the above, alkylsulfonylalkyl (a linear or branched 1 to 5 alkyl group having 1 to 8 carbon atoms) A linear or branched alkyl group having 1 to 3 carbon atoms substituted by a sulfonyl group), siloxyalkyl (1 to 5 —OSiR ⁵ R ⁶ R ⁷ (R ⁵ , R ⁶ , R ⁷ are carbon atoms) Straight chain or branched alkyl having 1 to 6 atoms, phenyl, 2 or all of which may be the same or all different substituents)) Or branched alkyl group), hydroxya Kill (a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 5 hydroxyl groups), alkoxyalkyl (a linear or branched 1 having 1 to 8 carbon atoms) A linear or branched alkyl group having 1 to 3 carbon atoms substituted by -5 alkoxy groups, a haloalkoxyalkyl (identical or different, carbon atoms substituted with 1 to 9 halogen atoms) A linear or branched alkyl group having 1 to 4 carbon atoms substituted with 1 to 4 linear or branched haloalkoxy groups having 1 to 4 carbon atoms, alkylthioalkyl (the number of carbon atoms is 1 to 8 linear or branched alkyl groups having 1 to 3 carbon atoms substituted with 1 to 5 linear or branched alkylthio groups), dialkoxy acetals (having 1 to 5 carbon atoms) 8 linear or branched a A dialkoxymethyl group in which a alkoxy group is substituted with 2 methyl groups), alkoxyalkoxy (1 to 1 carbon atoms substituted with 1 to 5 linear or branched alkoxy groups having 1 to 8 carbon atoms) 3 linear or branched alkyl groups), cyanoalkyl (C1-C3 linear or branched alkyl groups substituted by 1 to 5 cyano groups), halogen, cyano, nitro , Amino, hydroxy, pentahalosulfanyl, benzyl, benzyloxy, phenyl, phenoxy, pyridyl, oxazolyl, furyl, thiazolyl, naphthyl, pyrimidinyl, thienyl, benzothiazolyl, benzoxazolyl, benzooxolyl, imide, formyl (-CHO), carboxyl (—COOH) can be mentioned, but hydrogen atom, alkyl (for example, Til group, ethyl group, n-propyl group, isopropyl group), alkoxy (for example, methoxy group, ethoxy group, n-propoxy group, isopropoxy group), halogen (for example, fluorine atom, chlorine atom, bromine atom), cyano Haloalkyl (for example, monofluoromethyl group, difluoromethyl group, trifluoromethyl group, heptafluoroisopropyl group), cyanoalkyl (for example, cyanomethyl group, cyanoethyl group), haloalkoxy (for example, monofluoromethoxy group, difluoromethoxy group) And a trifluoromethoxy group) are preferred.

A represents phenylene, and the substituents include —C (O) OR, —C (O) R, —R, —OR, —SR, —SO ₂ R, —OC (O) R, —C (O _{) NHR, -C (O) NR} 2, -NHSO 2 R, -NRSO 2 R, -NHR, -NR 2, -NHC (O) R, -NRC (O) R, -NHC (O) OR, - NRC (O) OR, —N (OR) C (O) OR, —NHSO ₂ R, —NRSO ₂ R, —SO ₂ NHR, —SO ₂ NR ₂ (where R is from 1 to 8 carbon atoms) Linear or branched alkyl, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, or cyclohexane having 3 to 8 carbon atoms. alkyl or cycloalkenyl carbon atoms ^{3~8), - SiR 5 R 6} R 7, -OSiR 5 R ^{R 7 (R 5, R 6} , R 7 having 1 to 6 carbon atoms straight or branched alkyl, two or all phenyl may be all be the same substituent is different substituents), haloalkyl ( Linear or branched alkyl groups having 1 to 4 carbon atoms, which are the same or different and substituted with 1 to 9 halogen atoms, haloalkenyl (identical or different, with 1 to 4 halogen atoms) Linear or branched alkenyl groups having 2 to 6 carbon atoms), haloalkoxy (identical or different, and having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms) Linear or branched alkoxy group), acylalkoxy ((linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) -CO- 1-5 acyl groups Straight from 1 to 3 carbon atoms substituted by Or branched alkoxy groups), acyloxyalkyl ((linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) -CO-O- 1-5 acyloxy groups A linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1), alkylsulfonylalkyl (a linear or branched alkylsulfonyl group having 1 to 8 carbon atoms). A substituted or straight chain or branched alkyl group having 1 to 3 carbon atoms), siloxyalkyl (1 to 5 —OSiR ⁵ R ⁶ R ⁷ (R ⁵ , R ⁶ and R ⁷ are each 1 carbon atom) Linear or branched having 1 to 3 carbon atoms substituted by up to 6 linear or branched alkyls, phenyls, and two or all of them may be the same or different. Alkyl group), hydroxyalkyl (Linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 5 hydroxyl groups), alkoxyalkyl (linear or branched 1 having 1 to 8 carbon atoms) A linear or branched alkyl group having 1 to 3 carbon atoms substituted by -5 alkoxy groups, a haloalkoxyalkyl (identical or different, carbon atoms substituted with 1 to 9 halogen atoms) A linear or branched alkyl group having 1 to 4 carbon atoms substituted with 1 to 4 linear or branched haloalkoxy groups having 1 to 4 carbon atoms, alkylthioalkyl (the number of carbon atoms is 1 to 8 linear or branched alkyl groups having 1 to 3 carbon atoms substituted with 1 to 5 linear or branched alkylthio groups), dialkoxy acetals (having 1 to 5 carbon atoms) 8 linear or branched alco A dialkoxymethyl group in which two methyl groups are substituted with a methyl group), alkoxyalkoxy (1 to 1 carbon atoms substituted with 1 to 5 linear or branched alkoxy groups having 1 to 8 carbon atoms) 3 linear or branched alkyl groups), cyanoalkyl (C1-C3 linear or branched alkyl groups substituted by 1 to 5 cyano groups), halogen, cyano, nitro , Amino, hydroxy, pentahalosulfanyl, benzyl, benzyloxy, phenyl, phenoxy, pyridyl, oxazolyl, furyl, thiazolyl, naphthyl, pyrimidinyl, thienyl, benzothiazolyl, benzoxazolyl, benzooxolyl, imide, formyl (-CHO), carboxyl Optionally substituted with 1 to 4 substituents selected from (—COOH), Substitution or alkyl (for example, methyl group, ethyl group, n-propyl group, isopropyl group), alkoxy (for example, methoxy group, ethoxy group, n-propoxy group, isopropoxy group), halogen (for example, fluorine atom, chlorine) Atom, bromine atom), cyano, haloalkyl (eg, monofluoromethyl group, difluoromethyl group, trifluoromethyl group, heptafluoroisopropyl group), haloalkoxy (eg, monofluoromethoxy group, difluoromethoxy group, trifluoromethoxy group) ), 1 to 4 benzyloxy groups and phenoxy groups are preferably substituted.

The 5- or 6-membered heteroarylene diyl in A (heteroarene contains 1 to 3 N, O, and S atoms in the ring) includes oxazolediyl, isoxazolediyl, furandyl, thiazolediyl, isothiazolediyl , Pyrimidinediyl, pyrazinediyl, pyridinediyl, pyrrolediyl, thiophenediyl, imidazolediyl, and pyrazolediyl, and oxazolediyl, thiazolediyl, pyridinediyl, and thiophenediyl are preferable. As the substituent, -C (O) OR, -C (O) R, -R, -OR, -SR, -SO 2 R, -OC (O) R, -C (O) NHR, - C (O) NR ₂ , —NHSO ₂ R, —NRSO ₂ R, —NHR, —NR ₂ , —NHC (O) R, —NRC (O) R, —NHC (O) OR, —NRC (O) OR, —N (OR) C (O) OR, —NHSO ₂ R, —NRSO ₂ R, —SO ₂ NHR, —SO ₂ NR ₂ (where R is a straight chain having 1 to 8 carbon atoms) Or branched alkyl, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, cycloalkyl having 3 to 8 carbon atoms, or carbon atom the number is a 3-8 ^{cycloalkenyl), - SiR 5 R 6 R} 7, -OSiR 5 R 6 R 7 (R 5, R ⁶ , R ⁷ linear or branched alkyl having 1 to 6 carbon atoms, phenyl, two or all of which may be the same or different, and haloalkyl (identical or different, halogen Straight or branched alkyl group having 1 to 4 carbon atoms substituted with 1 to 9 atoms, haloalkenyl (identical or different, carbon atoms substituted with 1 to 4 halogen atoms) Linear or branched alkenyl group having 2 to 6 carbon atoms), haloalkoxy (same or different, linear or branched carbon atoms having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms) An alkoxy group), acylalkoxy ((a linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) -CO- substituted with 1 to 5 acyl groups represented by -CO- 1 to 3 linear or branched Alkoxy group), acyloxyalkyl ((linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) -CO-O-- substituted with 1 to 5 acyloxy groups Straight or branched alkyl group having 1 to 3 atoms), alkylsulfonylalkyl (carbon atom substituted with 1 to 5 linear or branched alkylsulfonyl groups having 1 to 8 carbon atoms) A linear or branched alkyl group of 1 to 3), siloxyalkyl (1 to 5 —OSiR ⁵ R ⁶ R ⁷ (R ⁵ , R ⁶ , R ⁷ are linear chains of 1 to 6 carbon atoms) A linear or branched alkyl group having 1 to 3 carbon atoms, which is substituted by a linear or branched alkyl or phenyl, and two or all of them may be the same substituent or all different substituents), Hydroxyalkyl (1-5 hydrides A linear or branched alkyl group having 1 to 3 carbon atoms substituted by a roxyl group, alkoxyalkyl (a linear or branched 1 to 5 alkoxy group having 1 to 8 carbon atoms) Straight or branched alkyl group having 1 to 3 carbon atoms), haloalkoxyalkyl (same or different, straight chain having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms) A linear or branched alkyl group having 1 to 3 carbon atoms substituted by a linear or branched 1 to 5 haloalkoxy group, alkylthioalkyl (a linear chain having 1 to 8 carbon atoms) Or a linear or branched alkyl group having 1 to 3 carbon atoms substituted with 1 to 5 branched alkylthio groups), dialkoxy acetal (linear or branched having 1 to 8 carbon atoms) -Like alkoxy group to methyl group 1-substituted dialkoxymethyl group), alkoxyalkoxy (a linear or branched carbon having 1 to 3 carbon atoms substituted by 1 to 5 linear or branched alkoxy groups having 1 to 8 carbon atoms) -Like alkoxy group), cyanoalkyl (C1-C3 linear or branched alkyl group substituted by 1 to 5 cyano groups), halogen, cyano, nitro, amino, hydroxy, pentahalo Select from sulfanyl, benzyl, benzyloxy, phenyl, phenoxy, pyridyl, oxazolyl, furyl, thiazolyl, naphthyl, pyrimidinyl, thienyl, benzothiazolyl, benzoxazolyl, benzooxolyl, imide, formyl (—CHO), carboxyl (—COOH) Optionally substituted with 1 to 3 substituents, unsubstituted or (For example, methyl group, ethyl group, n-propyl group, isopropyl group), alkoxy (for example, methoxy group, ethoxy group, n-propoxy group, isopropoxy group), halogen (for example, fluorine atom, chlorine atom, bromine) Atom), cyano, haloalkyl (for example, monofluoromethyl group, difluoromethyl group, trifluoromethyl group, heptafluoroisopropyl group), haloalkoxy (for example, monofluoromethoxy group, difluoromethoxy group, trifluoromethoxy group), benzyl It is preferable that 1 to 3 oxy groups and phenoxy groups are substituted.

Monocyclic or bicyclic rings optionally containing 0 to 3 heteroatoms in B include phenyl, benzyl, oxazolyl, isoxazolyl, furyl, benzofuryl, isobenzofuryl, dihydrobenzofuryl, thiazolyl, Isothiazolyl, naphthyl, pyrimidinyl, pyrazinyl, quinoxalyl, quinazolyl, pyridyl, quinolyl, isoquinolyl, benzothiazolyl, benzisothiazolyl, pyrrolyl, indolyl, isoindolyl, benzoxazolyl, benzoisoxazolyl, thienyl, benzothienyl, imidazolyl, benz Examples include imidazolyl, pyrazolyl, pyridonyl, triazinyl, triazolyl, thiadiazolyl, oxadiazolyl, tetrazolyl, ferrocenyl, phenyl, oxazolyl , Isoxazolyl, furyl, thiazolyl, isothiazolyl, pyrimidinyl, pyrazinyl, pyridyl, pyrrolyl, thienyl, imidazolyl, pyrazolyl are preferred, further phenyl, furyl, thiazolyl, pyridyl, thienyl are preferred. As the substituent, -C (O) OR, -C (O) R, -R, -OR, -SR, -SO 2 R, -OC (O) R, -C (O) NHR, - C (O) NR ₂ , —NHSO ₂ R, —NRSO ₂ R, —NHR, —NR ₂ , —NHC (O) R, —NRC (O) R, —NHC (O) OR, —NRC (O) _{OR, -N (OR) C (} O) OR, -NHSO 2 R, -NRSO 2 R, = NOR, R in _{-SO 2 NHR, -SO 2 NR 2} ( where 1 to 8 carbon atoms Linear or branched alkyl, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, or cycloalkyl having 3 to 8 carbon atoms , cycloalkenyl, or cyclic ethers having a carbon number of ^{3~8), - SiR 5 R 6} R 7, -OSi ^{5 R 6 R 7 (R 5} , R 6, R 7 having 1 to 6 carbon atoms straight or branched alkyl, two or all phenyl may be all be the same substituent is different substituents) Haloalkyl (same or different, linear or branched alkyl group having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms), haloalkenyl (same or different, 1 halogen atom A linear or branched alkenyl group having 2 to 6 carbon atoms substituted with ˜4, and a haloalkoxy (identical or different, the number of carbon atoms substituted with 1 to 9 halogen atoms is 1 -4 linear or branched alkoxy group), haloalkylthio (same or different, linear or branched alkylthio group having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms) ), Acylarco A straight chain having 1 to 3 carbon atoms substituted by 1 to 5 acyl groups represented by cis ((C 1-8 linear or branched aliphatic hydrocarbon group) -CO- Chain or branched alkoxy group), acyloxyalkyl ((linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) -CO-O- 1-5 acyloxy C1-C3 linear or branched alkyl group substituted by a group), alkylsulfonylalkyl (C1-C8 linear or branched alkylsulfonyl group having 1 to 8 carbon atoms) A linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1), siloxyalkyl (1 to 5 —OSiR ⁵ R ⁶ R ⁷ (R ⁵ , R ⁶ and R ⁷ are the number of carbon atoms) 1-6 linear or branched alkyl, phenyl, 2 Or a linear or branched alkyl group having 1 to 3 carbon atoms substituted by all or the same or different substituents), hydroxyalkyl (substituted by 1 to 5 hydroxyl groups) Carbon atoms substituted with 1 to 5 linear or branched alkoxy groups having 1 to 8 carbon atoms. Linear or branched alkyl group having 1 to 3 atoms), haloalkoxyalkyl (same or different, linear or branched having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms) Linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 5 haloalkoxy groups having a chain shape, alkylthioalkyl (straight or branched chain having 1 to 8 carbon atoms) 1-5 alkylthio A linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1) or dialkoxyacetal (a linear or branched alkoxy group having 1 to 8 carbon atoms substituted with 2 methyl groups) Dialkoxymethyl group), alkoxyalkoxy (a linear or branched group having 1 to 3 carbon atoms substituted by 1 to 5 linear or branched alkoxy groups having 1 to 8 carbon atoms) Alkoxy group), cyanoalkyl (a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 5 cyano groups), halogen, cyano, nitro, amino, hydroxy, pentahalosulfanyl, Benzyl, benzyloxy, phenyl, phenoxy, pyridyl, oxazolyl, furyl, thiazolyl, naphthyl, pyrimidinyl, thienyl, benzothiazolyl, benzoxa Optionally substituted with 1 to 7 substituents selected from lyl, benzooxolyl, imide, formyl (—CHO), carboxyl (—COOH), oxo (═O), unsubstituted, or alkyl (eg, methyl Group, ethyl group, n-propyl group, isopropyl group), alkoxy (for example, methoxy group, ethoxy group, n-propoxy group, isopropoxy group), halogen (for example, fluorine atom, chlorine atom, bromine atom), cyano, It is preferable that 1 to 7 haloalkyl groups (for example, monofluoromethyl group, difluoromethyl group, trifluoromethyl group, heptafluoroisopropyl group), benzyloxy group, and phenoxy group are substituted.

Linear or branched alkyl having 1 to 6 carbon atoms, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, Examples of the linear or branched cycloalkyl having 3 to 8 carbon atoms or the cycloalkenyl having 3 to 8 carbon atoms include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, s- Butyl group, t-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group, vinyl group, 1-propenyl group, 2-propenyl group, isopropenyl group, ethynyl group, propargyl group, cyclopropyl group , Cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, cyclopentenyl group, and cyclohexenyl group. Le group, n- propyl group, a vinyl group, a cyclopropyl group, a cyclopentyl group, a cyclohexyl group is preferred. As the substituent, -C (O) OR, -C (O) R, -R, -OR, -SR, -SO 2 R, -OC (O) R, -C (O) NHR, - C (O) NR ₂ , —NHSO ₂ R, —NRSO ₂ R, —NHR, —NR ₂ , —NHC (O) R, —NRC (O) R, —NHC (O) OR, —NRC (O) _{OR, -N (OR) C (} O) OR, -NHSO 2 R, -NRSO 2 R, = NOR, R in _{-SO 2 NHR, -SO 2 NR 2} ( where 1 to 8 carbon atoms Linear or branched alkyl, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, or cycloalkyl having 3 to 8 carbon atoms , cycloalkenyl, or cyclic ethers having a carbon number of ^{3~8), - SiR 5 R 6} R 7, -OSi ^{5 R 6 R 7 (R 5} , R 6, R 7 having 1 to 6 carbon atoms straight or branched alkyl, two or all phenyl may be all be the same substituent is different substituents) Haloalkyl (same or different, linear or branched alkyl group having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms), haloalkenyl (same or different, 1 halogen atom A linear or branched alkenyl group having 2 to 6 carbon atoms substituted with ˜4, and a haloalkoxy (identical or different, the number of carbon atoms substituted with 1 to 9 halogen atoms is 1 -4 linear or branched alkoxy group), haloalkylthio (same or different, linear or branched alkylthio group having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms) ), Acylarco A straight chain having 1 to 3 carbon atoms substituted by 1 to 5 acyl groups represented by cis ((C 1-8 linear or branched aliphatic hydrocarbon group) -CO- Chain or branched alkoxy group), acyloxyalkyl ((linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) -CO-O- 1-5 acyloxy C1-C3 linear or branched alkyl group substituted by a group), alkylsulfonylalkyl (C1-C8 linear or branched alkylsulfonyl group having 1 to 8 carbon atoms) A linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1), siloxyalkyl (1 to 5 —OSiR ⁵ R ⁶ R ⁷ (R ⁵ , R ⁶ and R ⁷ are the number of carbon atoms) 1-6 linear or branched alkyl, phenyl, 2 Or a linear or branched alkyl group having 1 to 3 carbon atoms substituted by all or the same or different substituents), hydroxyalkyl (substituted by 1 to 5 hydroxyl groups) Carbon atoms substituted with 1 to 5 linear or branched alkoxy groups having 1 to 8 carbon atoms. Linear or branched alkyl group having 1 to 3 atoms), haloalkoxyalkyl (same or different, linear or branched having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms) Linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 5 haloalkoxy groups having a chain shape, alkylthioalkyl (straight or branched chain having 1 to 8 carbon atoms) 1-5 alkylthio A linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1) or dialkoxyacetal (a linear or branched alkoxy group having 1 to 8 carbon atoms substituted with 2 methyl groups) Dialkoxymethyl group), alkoxyalkoxy (a linear or branched group having 1 to 3 carbon atoms substituted by 1 to 5 linear or branched alkoxy groups having 1 to 8 carbon atoms) Alkoxy group), cyanoalkyl (a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 5 cyano groups), halogen, cyano, nitro, amino, hydroxy, pentahalosulfanyl, Benzyl, benzyloxy, phenyl, phenoxy, pyridyl, oxazolyl, furyl, thiazolyl, naphthyl, pyrimidinyl, thienyl, benzothiazolyl, benzoxa And may be substituted with 1 to 7 substituents selected from ryl, benzooxolyl, imide, formyl (—CHO), carboxyl (—COOH), and oxo (═O). Alkyl (for example, methyl group, ethyl group, n-propyl group, isopropyl group), alkoxy (for example, methoxy group, ethoxy group, n-propoxy group, isopropoxy group), halogen (for example, fluorine atom, chlorine atom, bromine) It is preferable that 1 to 7 atoms, cyano, haloalkyl (for example, monofluoromethyl group, difluoromethyl group, trifluoromethyl group, heptafluoroisopropyl group), benzyloxy group, and phenoxy group are substituted.

—SiR ⁵ R ⁶ R ⁷ (R ⁵ , R ⁶ , R ^{7 in B} is linear or branched alkyl or phenyl having 1 to 6 carbon atoms, and even if two or all are the same substituents, Examples of different substituents include a trimethylsilyl group, a triethylsilyl group, a triisopropylsilyl group, a t-butyldimethylsilyl group, and a t-butyldiphenylsilyl group, and a trimethylsilyl group and a triethylsilyl group are preferable.

As B, —C (O) OR, —C (O) NHR, —C (O) NR ₂ , —SO ₂ NHR, —SO ₂ NR ₂ (where R is a carbon atom having 1 to 8 carbon atoms) Linear or branched alkyl, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, cycloalkyl having 3 to 8 carbon atoms Or cycloalkenyl having 3 to 8 carbon atoms, benzyl or cyclic ether), halogen, formyl (—CHO) or carboxyl (—COOH).

  In the present invention, the term “alkyl” represents a linear or branched alkyl group having 1 to 8 carbon atoms, such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, or an n-butyl group. , Isobutyl group, s-butyl group, t-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group, n-heptyl group, or n-octyl group.

  In the present invention, the term “alkenyl” refers to a linear or branched alkenyl group having 2 to 8 carbon atoms, such as ethenyl group, 1-propenyl group, 2-propenyl group, isopropenyl group, 1 -Butenyl group, 2-butenyl group, 3-butenyl group, etc. can be mentioned.

  In the present invention, the term “alkynyl” refers to a linear or branched alkynyl group having 2 to 8 carbon atoms, such as ethynyl group, 2-propynyl group, 2-butynyl group, or 3-butynyl. Groups and the like.

  In the present invention, the term “cycloalkyl” refers to a cycloalkyl group having 3 to 8 carbon atoms, and examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.

  In the present invention, the term “cycloalkenyl” refers to a cycloalkenyl group having 3 to 8 carbon atoms, for example, 1-cyclopentyl group, 2-cyclopentyl group, 3-cyclopentyl group, 1-cyclohexyl group, 2- A cyclohexyl group or a 3-cyclohexyl group can be exemplified.

  In the present invention, the term “heteroatom” includes a nitrogen atom, an oxygen atom, a sulfur atom and a silicon atom.

  In the present invention, the term “halogen” includes fluorine, chlorine, bromine and iodine.

  In the present invention, the term “halo” in “halo...” (For example, “haloalkyl”) includes fluorine, chlorine, bromine and iodine.

  In the present invention, the term “haloalkyl” is the same or different and represents a linear or branched alkyl group having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms. Examples thereof include a fluoromethyl group, a monochloromethyl group, a monobromomethyl group, a difluoromethyl group, a trifluoromethyl group, a pentafluoroethyl group, an n-heptafluoropropyl group, and an isoheptafluoropropyl group.

  In the present invention, the term “haloalkenyl” is the same or different and represents a linear or branched alkenyl group having 2 to 6 carbon atoms, which is substituted with 1 to 4 halogen atoms. , 2-difluoroethenyl group, 2,2-difluoroethenyl group, 3,3-difluoro-2-propenyl group, and the like.

  In the present invention, the term “alkoxy” refers to an (alkyl) -O— group in which the alkyl moiety has the above meaning, for example, a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group. , S-butoxy group, or t-butoxy group.

  In the present invention, the term “haloalkoxy” refers to a (haloalkyl) -O— group in which the haloalkyl moiety has the above meaning, for example, a monofluoromethoxy group, a difluoromethoxy group, a trifluoromethoxy group, 2,2-difluoro An ethoxy group, a 2,2,2-trifluoroethoxy group, etc. can be mentioned.

  In the present invention, the term “acyl” or the term “acyl” in acylalkoxy, the term “acyl” in acyloxyalkyl, and the term “acyl” in acyloxy are all (with 1 to 8 carbon atoms). A linear or branched aliphatic hydrocarbon group) -CO-, and examples thereof include an acetyl group, a propionyl group, a butyryl group, and an isobutyryl group. In the present application, the aliphatic hydrocarbon group means alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, and cycloalkynyl.

  In the present invention, the term “acylalkoxy” refers to a linear or branched alkoxy group having 1 to 3 carbon atoms substituted with 1 to 5 acyl groups as described above. Group, acetylethoxy group, acetylpropoxy group and the like.

  In the present invention, the term “acyloxy” refers to a (linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) —CO—O— group, for example, an acetoxy group, a propionyloxy group. , An isopropionyloxy group, or a pivaloyloxy group.

  In the present invention, the term “acyloxyalkyl” refers to a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 5 acyl groups as described above, for example, acetoxymethyl. A group, an acetoxyethyl group, an acetoxypropyl group, and the like.

In the present invention, the term “alkylsulfonyl” refers to an (alkyl) -SO ₂ — group in which the alkyl moiety has the above meaning, such as methylsulfonyl group, ethylsulfonyl group, n-propylsulfonyl group, or isopropylsulfonyl. Groups and the like.

  In the present invention, the term “alkylsulfonylalkyl” refers to a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 5 alkylsulfonyl groups shown above, for example, A methylsulfonylmethyl group, a methylsulfonylethyl group, or a methylsulfonylpropyl group can be exemplified.

In the present invention, the term “siloxy” is —OSiR ⁵ R ⁶ R ⁷ (R ⁵ , R ⁶ , R ⁷ are linear or branched alkyl having 1 to 6 carbon atoms, phenyl, and two Or all may be the same substituent or all different substituents), for example, trimethylsiloxy group, triethylsiloxy group, triisopropylsiloxy group, t-butyldimethylsiloxy group, t-butyldiphenylsiloxy group, etc. Can do.

  In the present invention, the term “siloxyalkyl” refers to a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 5 siloxy groups shown above, for example, trimethylsiloxy Examples thereof include a methyl group, a trimethylsiloxyethyl group, a trimethylsiloxypropyl group, a triethylsiloxymethyl group, and a t-butyldimethylsiloxy group.

  In the present invention, the term “hydroxyalkyl” refers to a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 5 hydroxyl groups, such as a hydroxymethyl group, hydroxyethyl group, and the like. Group, hydroxypropyl group, hydroxyisopropyl group and the like.

  In the present invention, the term “alkoxyalkyl” refers to a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 5 alkoxy groups shown above, for example, methoxymethyl A group, an ethoxymethyl group, a propoxymethyl group, or an isopropoxymethyl group.

  In the present invention, the term “alkylthio” refers to an (alkyl) -S— group in which the alkyl moiety has the above meaning, and examples include a methylthio group, an ethylthio group, or a propylthio group.

  In the present invention, the term “haloalkylthio” refers to a (haloalkyl) -S— group in which the haloalkyl moiety has the above meaning, for example, a monofluoromethylthio group, a difluoromethylthio group, a trifluoromethylthio group, 2,2- A difluoroethylthio group, a 2,2,2-trifluoroethylthio group, etc. can be mentioned.

  In the present invention, the term “alkylthioalkyl” refers to a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 5 alkylthio groups shown above, for example, methylthiomethyl A group, an ethylthiomethyl group, a methylthioethyl group, or an ethylthioethyl group.

  In the present invention, the term “dialkoxyacetal” refers to a dialkoxymethyl group in which the above-mentioned alkoxy group is substituted by two methyl groups, such as a dimethoxymethyl group, a diethoxymethyl group, or a dipropoxymethyl group. Can be mentioned.

  In the present invention, the term “alkoxyalkoxy” refers to a linear or branched alkoxy group having 1 to 3 carbon atoms substituted by 1 to 5 alkoxy groups as described above, for example, methoxymethoxy Group, methoxyethoxy group, methoxypropoxy group and the like.

  In the present invention, the term “haloalkoxyalkyl” refers to a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 5 haloalkoxy groups as described above. A monofluoromethoxymethyl group, a difluoromethoxymethyl group, a trifluoromethoxymethyl group, etc. can be mentioned.

  In the present invention, the term “cyanoalkyl” represents a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 5 cyano groups, such as a cyanomethyl group, a cyanoethyl group, Or a cyanopropyl group etc. can be mentioned.

  In the present invention, “phenyl”, “oxazolyl”, “isoxazolyl”, “furyl”, “benzofuryl”, “isobenzofuryl”, “dihydrobenzofuryl”, “thiazolyl”, “isothiazolyl”, “naphthyl”, “pyrimidinyl” ”,“ Pyrazinyl ”,“ quinoxalyl ”,“ quinazolyl ”,“ pyridyl ”,“ quinolyl ”,“ isoquinolyl ”,“ benzothiazolyl ”,“ benzoisothiazolyl ”,“ pyrrolyl ”,“ indolyl ”,“ isoindolyl ”,“ Benzoxazolyl, benzoisoxazolyl, thienyl, benzothienyl, imidazolyl, benzimidazolyl, pyrazolyl, pyridonyl, triazinyl, triazolyl, thiadiazolyl , Oxadiazolyl, benzodioxoli "," Tetrazolyl "," ferrocenyl "may have one or more substituents the same or different, may not have a substituent.

  In the present invention, the term “phenoxy” includes phenoxy groups having one or more substituents which may be the same or different, and unsubstituted phenoxy groups.

  In the present invention, the term “benzyl” includes a benzyl group having one or more substituents which are the same or different and an unsubstituted benzyl group.

  In the present invention, the term “benzyloxy” includes a benzyloxy group having one or more substituents which are the same or different and an unsubstituted benzyloxy group.

  In the present invention, the term “propargyl” includes a propargyl group having a substituent at the alkyne end and an unsubstituted propargyl group.

  In the present invention, the term “propargyloxy” includes a propargyloxy group having a substituent at the alkyne end and an unsubstituted propargyloxy group.

  In the present invention, the term “heteroaryl” is oxazolyl, isoxazolyl, furyl, benzofuryl, isobenzofuryl, dihydrobenzofuryl, thiazolyl, isothiazolyl, naphthyl, pyrimidinyl, pyrazinyl, quinoxalyl, quinazolyl, pyridyl, quinolyl, isoquinolyl, benzothiazolyl, Includes benzoisothiazolyl, pyrrolyl, indolyl, isoindolyl, benzoxazolyl, benzisoxazolyl, thienyl, benzothienyl, imidazolyl, benzimidazolyl, pyrazolyl, pyridonyl, triazinyl, triazolyl, thiadiazolyl, oxadiazolyl, tetrazolyl, ferrocenyl . These groups may have one or more substituents which may be the same or different, and may not have a substituent.

  In the present invention, the term “phenylene” includes 1,2-phenylene (o-phenylene), 1,3-phenylene (m-phenylene) and 1,4-phenylene (p-phenylene). These groups may have one or more substituents which may be the same or different, and may not have a substituent.

  In the present invention, the term “5- or 6-membered heteroallene” containing 1 to 3 N, O and S atoms in the ring indicates an aromatic heterocycle having 5 or 6 ring atoms, for example, Examples thereof include oxazole, isoxazole, furan, thiazole, isothiazole, pyrimidine, pyrazine, pyridine, pyrrole, thiophene, imidazole, and pyrazole.

  In the present invention, the term “5- or 6-membered heteroarrangeyl” is a divalent group derived from the aromatic heterocycle having 5 or 6 ring atoms shown above, and the position of the bond at two positions. For example, oxazolediyl, isoxazolediyl, furandyl, thiazolediyl, isothiazolediyl, pyrimidinediyl, pyrazinediyl, pyridinediyl, pyrroldiyl, thiophenediyl, imidazolediyl, pyrazolediyl, pyridonediyl, etc. Can be mentioned.

  In the present invention, the term “cyclic ether” includes epoxy, oxetane, tetrahydrofuran, tetrahydropyran, dioxolane, and dioxane.

  In the present invention, the term “cyclic amine” includes pyrrolidinyl, imidazolidinyl, pyrazolidinyl, piperidinyl, piperazinyl, morpholinyl.

  In the present invention, the term “imide” includes a chain imide and a cyclic imide.

  Since the compound of the present invention represented by the formula [I] has a pyridyl group, an acid addition salt derived therefrom is also included in the present invention.

  Examples of acids that form acid addition salts include inorganic acids such as hydrochloric acid, hydrobromic acid, nitric acid, sulfuric acid, and phosphoric acid, formic acid, acetic acid, oxalic acid, fumaric acid, adipic acid, stearic acid, oleic acid, and aconite. Examples thereof include carboxylic acids such as acids, and sulfonic acids such as methanesulfonic acid, benzenesulfonic acid, and p-toluenesulfonic acid.

  As shown in the following reaction step, the present compound [I] represented by the following formula comprises, for example, a sulfonic acid derivative represented by the general formula [II] and an amine derivative represented by the general formula [III] as a base (base). ) And a solvent in the presence of a solvent.

（式中、Ｒ^１，Ｒ^２，Ｒ^３，Ｒ^４，Ａ及びＢは、前記と同義である。）

(In the formula, R ¹ , R ² , R ³ , R ⁴ , A and B are as defined above.)

  Moreover, when compound [I] manufactured as mentioned above is terminal alkyne (B = H, compound I-1), it is also possible to introduce | transduce a substituent using a coupling reaction.

（式中、Ｘは臭素またはヨウ素、Ｂはフェニル、ヘテロアリール、アルケニル、Ｒ^１，Ｒ^２，Ｒ^３，Ｒ^４及びＡは、前記と同義である。）

(Wherein X is bromine or iodine, B is phenyl, heteroaryl, alkenyl, R ¹ , R ² , R ³ , R ⁴ and A are as defined above.)

  Furthermore, it is also possible to introduce a substituent from compound [I-2] and terminal alkyne [V] using a coupling reaction.

（式中、Ｘは臭素またはヨウ素、Ｒ^１，Ｒ^２，Ｒ^３，Ｒ^４，Ａ及びＢは、前記と同義である。）

(In the formula, X is bromine or iodine, and R ¹ , R ² , R ³ , R ⁴ , A and B are as defined above.)

[Control effect]
In the present invention, the term “pest” includes all pests on agricultural and horticultural plants and all pathogenic fungi on agricultural and horticultural plants.

  Examples of agricultural and horticultural pests that have a control effect with the compound (I) of the present invention are shown below.

(Pathogenic fungi against agricultural and horticultural plants)
Examples of pathogenic fungi for agricultural and horticultural plants include Plasmodiophoromycota, Omyycota, Zygomycota, Ascomycota, Basidiomycota, Incomplete fungus ( Deuteromycota) and bacteria belong, and the sulfonamide derivative according to the present invention can control plant diseases caused by these pathogenic fungi. Next, specific names of bacteria are given as examples, but are not necessarily limited thereto.

Examples of agricultural and horticultural pathogens include, for example, rice blast (Pyricularia oryzae), rice sesame leaf blight (Cochliobolus miyabeanus), rice blight (Rhizoctonia solani), rice idiot (Gibberella fujikuroi), wheat red mold (Gibberella zeae) ), Wheat red rust (Puccinia recondita), wheat powdery mildew (Erysiphe graminis f.sp. Sclerotinia borealis, wheat syrup, Typhula ishikariensis, Streptomyces scabies, Phytophthora infestans, Thanatephorus cucumeris, potato Anthracnose (Colletotrichum atramentarium), potato summer plague (Alternaria solani), azuki bean powder (Erisiphe pisi), azuki bean disease (Cercospora canescens), azuki bean sclerotia (Sclerotinia sclerotioru) m), azuki bean anthracnose (Colletotrichum phaseolorum), kidney bean brown spot (Cercospora canescens), kidney bean sclerotia (Sclerotinia sclerotiorum), bean anthracnose (Colletotrichum lindemuthiamum), kidney bean gray mold (Botrytis cinerea) Phakopsora pachyrhizi), soybean purple spot (Cercospora kikuchii), soybean anthracnose (Colletotrichum truncatum), sugar beet brown spot (Cercospora beticola), konjac anthracnose (Gloeosporium conjac), konjac brown spot (Septoria perillae) (Pseudomonas syringae), tea net blast (Exobasidium reticulatum), tea brown rot (Pseudocercospora ocellata, Cercospora chaae), tea anthracnose (Colletotrichum theae-sinensis), tea blast (Exobasidium vexans), tea ring spot ( Pestalotiopsis longiseta), Japanese Shiva Carbaria leaf blight (Curvularia geniculata), Japanese Shiba leaf rot (Rhizoctonia solani), Bentgrass red blight (Pythium aphanidermatum), Bentgrass Dollar spot disease (Sclerotinia homoeocarpa), Bentgrass Picium disease (Pythium vanterpoolii, Pythium graminicola), Spinach brown spot (Cercospora beticola), Spinach anthracnose (Colletotrichum spinaciae), Spinach downy mildew (Peronospora effusa) (Albugo macrospora), cabbage black rot (Xanthomonas campestris pv. Campestris), cabbage mycosis (Sclerotinia sclerotiorum), cabbage black soot (Alternaria brassicicola), cabbage downy mildew (Peronospora parasitica), radish soft rot (Erwinia carotovora) ), Colletotrichum higginsianum, Sclerotinia sclerotiorum, Chinese cabbage black spot (Alternaria brassicae, Alternaria brassicicola), Chinese cabbage root-knot (Plasmodiophora brassicae), Pumpkin black spot (Alternaria cucumerina) Plague (Phytophthora capsici), pumpkin downy mildew (Pseudoperonospora cubensis), cucumber spotted fine Diseases (Pseudomonas syringae), cucumber powdery mildew (Sphaerotheca cucurbitae), cucumber plague (Phytophthora melonis), cucumber brown spot (Corynespora cassiicola), cucumber sclerotia (Sclerotinia sclerotiorum), cucumber black cucumber (Al) Anthracnose (Colletotrichum orbiculare), Cucumber vine blight (Didymella bryoniae), Cucumber vine split (Fusarium oxysporum f.sp. cucumerinum), Cucumber seedling blight (Pythium cucurbitacearum, Rhyzoctonia solani), cucumber gray tis ), Cucumber downy mildew (Pseudoperonospora cubensis), Watermelon powdery mildew (Sphaerotheca fuliginea), Watermelon plague (Phytophthora cryptogea), Watermelon anthracnose (Colletotrichum orbiculare), Watermelon downy mildew (Pseudoperonospora cubensis), Melon brown spot disease cassiicola), melon sclerotia (Sclerotinia sclerotiorum), melon vine split disease (Fusarium oxysporum f.sp. melonis), melon downy mildew (Pseudoperonospora cubensis), Fusarium oxysporum, Sclerotinia sclerotiorum, Puccinia cnici-oleracei, Shungiku anthracnose (Gloeosporium chrysanthemi, Gloeosporium carthami), Ginger timul var Carrot wilt (Fusarium oxysporum), carrot powdery mildew (Erysiphe heraclei), carrot mycosis (Sclerotinia intermedia, Sclerotinia sclerotiorum), carrot black leaf blight (Alternaria dauci), carrot black spot (Alternaria radicina), red pepper Pepper bacterial wilt (Ralstonia solanacearum), Pepper pepper pepper powdery mildew (Oidiopsis sicula), Pepper pepper, Phytophthora capsici, Pepper pepper sclerotior disease (Sclerotinia sclerotiorum), Pepper glo rio pole Capsici pepper pepper (Cercospora capsici), tomato wilt (Fusarium oxysporum f.sp.lycopersici) ), Tomato powdery mildew (Oidium violae, Oidiopsis sicula), tomato plague (Phytophthora infestans), tomato mycosis (Sclerotinia sclerotiorum), tomato gray mold (Botrytis cinerea), tomato leaf mold (Fulvia fulva), tomato spots Disease (Stemphylium lycopersici), tomato ring rot (Alternaria solani), eggplant plague (Phytophthora infestans), eggplant brown spot disease (Thanatephorus cucumeris), eggplant brown rot (Phytophthora capsici), eggplant subtilis (Mycovellosiella nattrassii) Half body wilt (Verticillium dahliae), strawberry wilt (Fusarium oxysporum), strawberry wilt (Verticillium dahliae), strawberry powdery mildew (Sphaerotheca humuli), strawberry plague (Phytophthora nicotianae var. Parasitica), strawberry fruit rot (Pythium ultimul) var.ultimum), strawberry sclerotia (Sclerotinia sclerotiorum), strawberry black spot (Alternaria alternata), strawberry snake eye disease (Mycosphaerella fragariae), strawberry anthracnose (Colletotrichum acutatum, Glomerella c) ingulata), strawberry gray mold (Botrytis cinerea), asparagus brown spot (Cercospora asparagi), asparagus stem blight (Phomopsis asparagi), asparagus rust (Puccinia asparagi-lucidi), asparagus anthracnose (Colletotrichum gloeosporioides) ), Asparagus gray mold disease (Botrytis cinerea), Asparagus spot disease (Stemphylium botryosum), Onion plague (Phytophthora nicotianae), Onion yellow spot (Cladosporium allii-cepae), Onion dry rot (Fusarium oxysporum f.sp. ), Onion sclerotia (Sclerotinia sclerotiorum), onion black spot blight (Septoria alliacea), onion black spot (Alternaria porri), onion rust (Puccinia allii), onion small sclerotia (Sclerotinia allii), small onion Botrytis squamosa, onion white plague (Phytophthora porri), onion anthracnose (Colletotrichum circinans), onion gray mold (Botrytis cinerea), onion gray rot (Botrytis a llii), onion leaf blight (Pleospora herbarum), onion downy mildew (Peronospora destructor), leek rust (Puccinia allii), leek white leaf blight (Botrytis byssoidea), leek plague (Phytophthora nicotianae), leek wilt ( Fusarium oxysporum f. Sp. Cepae), leeks black astringency (Mycosphaerella allicina), leeks black leaf blight (Septria alliacea), leeks black spot (Alternaria porri), leeks sclerotia nuclear disease (Sclerotinia allii), leeks rust (Puccinia allii), green onion rot (Botrytis squamosa), green onion blight (Phythoththora porri), green onion anthracnose (Colletotrichum circinans), leek downy mildew (Peronospora destructor), chrysanthemum black spot (Septoria chrysanthemella), Chrysanthemum rust (Puccinia horiana), mango anthracnose (Colletotrichum gloeosporioides), oyster powdery mildew (Phyllactinia kakicola), oyster keratosis (Cercospora kakivora), oyster keratosis (Cercospora kaki), oyster brown spot ( Macrophoma kaki), oyster black spot disease (Fusicladium levieri), oyster black spot disease (Phomop) sis kakivora), oyster black spot disease (Pseudocercospora fuliginosa), oyster leaf blight (Physalospora kaki), oyster scab (Aureobasidium pullulans, Capnophaeum fuliginodes, Cladosporium herbarum, Microxyphium sp., Scorias communis, Triposperm muss (Zygophiala jamaicensis), oyster anthracnose (Gloeosporium kaki), oyster gray fungus (Botrytis cinerea), oyster leaf blight (Pestalotia diospyri), oyster lobster rot (Mycosphaerella nawae), banana anthracnose (Colletotrichum musae), ume Powdery mildew (Podosphaera tridactyla, Sphaerotheca pannosa), ume branch blight (Botryosphaeria dothidea), ume mycosis (Sclerotinia sclerotiorum), ume black scab (Cladosporium carpophilum), ume leaf rust (Taphrina mume), ume white rust (Leucotelium pruni-persicae), ume white blight (Rosellinia necatrix), ume heart rot (Fusarium lateritium), ume fistula (Pseudocercospora circumscissa), ume scab (Sphaceloma pruni-domesticae), ume anthrax (Glomerell) a cingulata), ume gray mold disease (Botrytis cinerea), ume gray scab disease (Monilinia fructicola, Monilinia laxa), sweet powdery mildew (Podosphaera tridactyla), sweet potato nuclear disease (Sclerotinia sclerotiorum), sweet potato black mold (Rhizopus gri) ), Sweet potato anthracnose (Glomerella cingulata), sweet potato gray fungus (Botrytis cinerea), sweet pea scab (Monilinia fructicola), pear powdery mildew (Phyllactinia mali), pear plague (Phytophthora cactorum, phytae) Pear black spot disease (Venturia pirina), pear anthracnose disease (Colletotrichum gloeosporioides), pear red star disease (Gymnosporangium asiaticum), pear black spot disease (Venturia nashicola), pear black spot disease (Alternaria kikuchiana), pear soot spot disease (Leptothyrium pomitus) , Pear anthracnose (Glomerella cingulata), pear gray mold (Botrytis cinerea), pear ash scab (Monilinia fructigena), pear leaf anthracnose (Colletotrichum gloeosporioides), pear ring rot (Ph ysalospora piricola), peach red mold disease (Fusarium oxysporum, Gibberella zeae), peach powdery mildew (Podosphaera tridactyla, Sphaerotheca pannosa), peach sclerotia (Sclerotinia sclerotiorum), peach black mold disease (Rhizopus nigris) Cladosporium carpophilum), peach leaf rust (Leucotelium pruni-persicae), peach scab (Stenella sp.), Peach perforation (Pseudocercospora circumscissa, Phyllosticta persicae), peach anthracnose (Gloeosporium laeticolor), peach gray rust cinerea), peach ash scab (Monilinia fructicola), peach homoposis rot (Phomopsis sp.), apple red scab (Gymnosporangium yamadae), apple powdery mildew (Podosphaera leucotricha), apple blight (Phytophthora cactorum, phytophthora cophora ), Apple brown spot (Diplocarpon mali), apple ring-rot (Cristulariella moricola), apple black spot (Venturia inaequalis), apple soot spot (Zygophiala jamaicensis), apple soy Leaf spot (Gloeodes pomigena), apple spotted leaf disease (Alternaria mali), apple purple herb disease (Helicobasidium mompa), apple ringworm (Botryosphaeria berengeriana), grape powdery mildew (Uncinula necator), grape blight fungus nuclear disease (Sclerotinia sclerotiorum), grape late rot (Glomerella cingulata), grape brown spot (Pseudocercospora vitis), grape brown leaf blight (Briosia ampelophaga), grape black rot (Phyllosticta ampelicida), grape black rot (Elsinoe ampelina) ), Grape soot spot disease (Zygophiala jamaicensis), grape vine split disease (Phomopsis viticola), grape downy mildew (Plasmopara viticola), chestnut powdery mildew (Microsphaera alphitoides), chestnut brown spot (Morenoella quercina), chestnut soot disease (Capnodium salicinum), chestnut anthracnose (Glomerella cingulata), chestnut leaf blight (Monochaetia monochaeta), citrus scab (Xanthomonas campestris), citrus green mold (Penicillium italicum), citrus yellow spot (Mycosphaerella citri, Mycosphaer h orii), citrus brown rot (Phytophthora citrophthora), citrus black spot (Diaporthe citri), citrus soot spot (Leptothyrium pomi), citrus scab (Elsinoe fawcettii), citrus buckwheat (Mycosphaerella pinodes), citrus charcoal Colleto
trichum gloeosporioides) and citrus green mold (Penicillium digitatum).

(Pests and mites on agricultural and horticultural plants)
Examples of pests and mites on agricultural and horticultural plants include the order of Hemiptera, Thysanoptera, Lepidoptera, Acari, etc., and the sulfonamide derivatives used in the present invention Can control plant damage caused by these pests, mites and the like. Next, specific pests, ticks and the like are given as examples, but not necessarily limited thereto.

  Examples of the pests and mites include, for example, Cossus insularis, Adoxophyes honmai, Adoxophyes orana faciata, Grapholita molesta, Chamonaki (Homona magnamina), Leguminivora glycinivorella), Lyonetia prunifoliella malinella, Chanohosuga (Caloptilia theivora), Butterflies (Phyllonorycter ringoniella), Citrus moth (Phyllocnistis citrella), Negikoga (Acres) conjugella), Grape squirrel (Nokona regalis), Cossock squirrel (Synanthedon hector), Stathmopoda masinissa, Peach squirrel (Carposina sasakii), Iraga (Monema flavescens), Chilli suppressalis, Cypno halo cis cis Hellula undalis), Australia furnacalis, Parapediasia teterrella, Ephestia kuehniella, Galleria gulonella, Papilio machaon hippocrates, Pirolio machaon hippocrates Artemisia, Ascotis selenaria, Agrius convolvuli, Orgyia thyellina, Hyphantria cunea, Agrotis ipsilon, Agrotis segetum, Agrotis segetum, Tuna Trichoplusia ni, Helicoverpa armigera, Helicoverpa assulta, Mamestra brassicae, Mythimna separata, Naranga aenescens, Slitoptera exigua, Slitoptera exigua, Worm (Helicoverpa zea), Tobacco Bud Worm (Heliothis virescens), Cotton Leaf Worm (Spodoptera littoralis), Fritiperidae (Spodoptera frugiperda), Southern Army Worm (Spodoptera eridania), Tobacco Hornworm (Manduca sexta) (Endopiza viteana), cotton beetle (Pectinophora gossypiella), codling moth (Cydia pomonella), European corn borer (Ostrinia nubilalis), soybean looper (Pseudoplusia includens), etc. (Popillia japonica), Japanese horned beetle (Melanotus tamsuyensis), Japanese black beetle (Anthrenus verbasci), Henosepilachna vigintioctopunctata, Japanese white beetle (Tenebrio molitor casta, Tenebrio molitor Anoplophora malasiaca, Monochamus alternatus endai, Azuki beetle (Callosobruchus chinensis), Aurihamushi (Aulacophora femoralis), Phyllotreta striolata (Cylas forsicum weevil) oryzophilus, Sweeophilus zeamais, Sphenophorus venatus vestius, Cotton weevil (Anthonomus grandis), Rhynchites heros, Tobacco (Lasioderma serricorne), Larva Oulema oryzae), Alfalfa weevil (Hypera postica), Colorado potato beetle (Lepinotarsa decemlineata), Granaria weevil (Sitophilus granarius), Jupiter weevil (Diabrotica undecimpunctata), Western corn root worm (Diabrotica) virgifera virgifera), Northern corn rootworm (Diabrotica longicormis barberi), Aedes aegypti (Paederus fuscipes), etc. Empoasca onukii), leafhopper leafhopper (Nephotettix cincticeps), brown leafhopper (Laodelphax striatella), leafhopper (Nilaparvata lugens), white leafhopper (Sogatella furcifera), citrus leafworm (Diaphorina citri) Aphids (Aulacorthum solani), radish aphids (Brevicoryne brassicae), apple rotifers (Eriosoma lanigerum), peach aphids (Myzus persicae), wheat leaf beetle (Rhopalosiphum padi), tobacco whitefly (Bemisia tabaci) (Trialeurodes vaporariorum), Pseudodococcus comstocki, horn beetle (Ceroplastes ceriferus), ruby rot beetle (Ceroplastes rubens), trichonotylus caelestialium, yssi moss Stink bugs (Eysarcoris ventralis), Chabae stink bugs (Plautia crossota stali), Spider helicopter bugs (Leptocorisa chinensis), Holy spider stink bugs (Riptortus clavatus), Japanese turtles (Eurydema rugosa), Japanese crested stink bugs (Halyomorpha ha) ), White-footed beetle (Togo hemipterus), potato leafhopper (Empoasca fabae), citrus whitefly (Dialeurodes citri), Icerya purchasi, Iranya scale (Unaspis yanonensis), octopus (Ci mex lectularius, etc. , Fruit fly (Bactrocera dorsalis), fruit fly (Bactrocera cucurbitae), fruit fly (Ceratitis capitata), beetle fly (Liriomyza trifolii), leaf fly (Chromatomyia horticola), tomato leaf fly (Li) , Rhagoletis pomonella, Mayetiola destructor, Musca domestica, Stomoxys calcitrans, Melophagus ovinus, Hypoderma lineatum, Hypoderma lineatum, Vis oest One species of the tsetse fly (Glossina palpalis, Glossina morsitans), Black-headed ayu (Prosimulium yezoensis), Bovine abalone (Tabanus trigonus), Great fly (Telmatoscopus albipunctatus), Tokunagaka (Leptoconops nipponensis), Leptoconops nipponensis (Aedes aegypti), Fenoptera (Anopheles hyracanus sinesis), etc. , Black-tailed ants (Camponotus japonicus), Greater hornet (Vespa mandarina japonica), Bulldog ant (Myrmecia spp.), Hiari (Solenopsis spp.), Yellow-tailed ants (Monomorium pharaonis) (Periplaneta japonica), Cockroaches such as Blattella germanica, Teleogryllus emma, Gryllotalpa orientalis, Locusta migratoria, Oxya yezoensis, gregaria, gregaria, etc. Termites pests such as Coptotermes formosanus), Yamato termites (Reticulitermes speratus), and Thai termites (Odontotermes formosanus), cat fleas (Ctenocephalidae felis), human fleas (Pulex irritans), and chino pests (Xenopsylla cheops) Lice insects such as white lice (Menacanthus stramineus), white lice (Damalinia bovis), white lice, Haematopinus eurysternus, Linognathus vituli, and Solenopotes capillatus. As for the mites, spider mites (Panonychus citri), apple spider mites (Panonychus ulmi), Kanzawa spider mites (Tetranychus kanzawai), spider mites (Aceria tulipae), tomato spider mites (Aculops lycopers) Acarops pelekassi and other mites, Rhizoglyphus robini, spinach mite (Tyrophagus similis) and other mites, Polyphagotarsonemus latus and other mites, honey bees Ticks, such as ticks (Boophilus microplus), ticks (Haemaphysalis longicornis), cucumbers, such as Psoroptes ovis, and ticks, such as Sarcoptes scabiei. In addition, crustaceans such as Armadillidium vulgare, Meloidogyne incognita, Meloidogyne hapla, potato cyst nematode (Globodera rostochiensis), Heterodera thyPene, penis , Nematodes such as Plethylenchus vulnus, Aphelenchoides besseyi and Bursaphelenchus xylophilus, Ponacea canaliculata, Meghimatebta ), And mollusks such as Lehmannina valentiana.

[Pesticides]
The agricultural and horticultural pest control agent of the present invention is particularly effective in sterilizing effect and insecticidal effect, and contains one or more compounds represented by the formula [I] as active ingredients.

  The compound of the present invention represented by the formula [I] is applied to the plant by spraying, spraying, applying, or the like with the active ingredient, or sowing the seed of the plant or the soil or seed around the plant. It can be performed by treating soil, paddy field, hydroponics water with active ingredients. When used as a fungicide, the application can be done before or after the plant is infected with the pathogen. When used as an insecticide, application can be performed before or after the occurrence of pests.

  This compound is in the form of normal preparations such as granules, powders, aqueous solvents, oils, emulsions, microemulsions, suspoemulsions, solutions, wettable powders, emulsions, suspensions, tablets, granules It can be used as an agent suitable for agricultural and horticultural pest control agents such as wettable powders, microcapsules, aerosols, pastes, jumbo agents, powders, smoke agents, fumigants and the like. Such embodiments include at least one compound of the invention and a suitable solid or liquid carrier, and, if desired, suitable adjuvants (eg, surfactants) to improve the dispersibility of the active ingredient and other properties. Can be obtained by an ordinary method of mixing with an agent, a solvent and a stabilizer.

  Examples of solid carriers or diluents include plant materials (eg, crystalline cellulose, starch, wood flour, cork, coffee husk, etc.), fibrous materials, artificial plastic powders, clays (eg, kaolin, bentonite) , White clay, diatomaceous earth, synthetic hydrous silicon oxide, fusami clay, acid clay, etc., talc and minerals (eg, vermulite, montmorillonite, pumice, sulfur powder, apatite, mica, sericite, quartz powder, activated carbon, calcium carbonate Etc.), polymer compounds (polyvinyl chloride, petroleum resins, etc.), chemical fertilizers (eg, ammonium sulfate, phosphorous acid, ammonium nitrate, ammonium chloride, calcium chloride, urea, etc.). Liquid carriers and diluents include water, alcohols (eg, methanol, ethanol, isopropanol, cyclohexanol, etc.), ketones (eg, acetone, methyl ethyl ketone, cyclohexanone, etc.), ethers (eg, ethyl cellosolve, butyl cellosolve) , Dioxane, etc.), aromatic hydrocarbons (eg, benzene, toluene, xylene, ethylbenzene, methylnaphthalene, etc.), aliphatic hydrocarbons (eg, kerosene, paraffin, etc.), and swells (eg, isopropyl acetate, benzyl acetate, etc.) , Nitriles, amides (for example, N, N-dimethylformamide, dimethyl sulfoxide, etc.), halogenated hydrocarbons (for example, chlorobenzene, trichloroethylene) and the like.

  Examples of the gaseous carrier, that is, the propellant, include carbon dioxide gas, butane gas, and fluorocarbon.

  Examples of the surfactant include various anionic surfactants and nonionic surfactants conventionally used in the agricultural chemical formulation field. Examples of the anionic surfactant include sulfonic acid-based surfactants such as alkyl sulfonic acid, alpha olefin sulfonic acid, lignin sulfonic acid, alkylbenzene sulfonic acid, alkyl naphthalene sulfonic acid, naphthalene sulfonic acid formalin condensate, and dialkyl sulfosuccinate. Agents and salts thereof, polyoxyethylene alkyl ether sulfate, polyoxyethylene alkyl allyl ether sulfate, polyoxyethylene styryl phenyl ether sulfate, polyoxyethylene phenyl alkyl allyl ether sulfate, polyoxyalkylene glycol sulfate, higher alcohol sulfate, fatty acid ester Sulfate surfactants such as sulfate and phenylphenol (EO) sulfate and the like Salts of polyoxyethylene alkyl ether phosphate, polyoxyethylene alkyl allyl phosphate, phenylphenol (EO) phosphate ester salt, polyoxyethylene phenyl alkyl allyl ether phosphate, higher alcohol phosphate, polyoxyethylene tribenzylphenol phosphate, etc. Surfactants and salts thereof, higher fatty acid salts, polycarboxylic acid type surfactants and salts thereof, and the like. The salts in the above surfactants include salts of sodium, potassium, magnesium, calcium, ammonium, ethanolamine, diethanolamine, triethanolamine, various amines and the like. Examples of the nonionic surfactant include polyoxyethylene alkyl allyl ether, polyoxyethylene styryl phenyl ether, polyoxyethylene alkyl ether, polyoxyethylene phenyl alkyl allyl ether, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene glycol. , Polyoxyethylene alkyl ester, polyoxyethylene polyoxypropylene block copolymer, polyoxyalkylene glycol, alkyne diol (acetylene glycol), alkynylene polyoxyethylene diol, sorbitan fatty acid ester, alkyl aryl ether formalin condensate, etc. it can.

  Stabilizers include isopropyl phosphate mixtures, tricresyl phosphate, true oil, epoxy oil, surfactants, fatty acids and esters thereof. In addition to the above components, the compounds of the present invention can be formulated in admixture with other fungicides, insecticides, herbicides, or fertilizers.

  Generally, the above preparation contains 1 to 95% by weight, preferably 1 to 50% by weight, of at least one compound [I] of the present invention. These preparations can be used alone or diluted, and the compound [I] of the present invention is used in an amount of about 1 g to 5 kg / ha, preferably about 2 g to 100 g / ha, usually about 1 to 50000 ppm, preferably about Used at a concentration of 50-1000 ppm.

  The compound of the present invention represented by the formula [I] can be used alone or as a preparation thereof, but a bactericidal / fungicidal agent, bactericidal agent, acaricide, nematicide, insecticide, biological pesticide, A mixture of herbicides, plant hormones, plant growth regulators, synergists, attractants, repellents, pigments, fertilizers, etc., or a mixture of one or more selected from those active ingredients The preparation can also be used as a pest control agent. There, it can be expected that the action, pests to be controlled, expansion of the appropriate period of use, or reduction of dosage, synergistic effect, or prevention of development of resistance, etc. Shinogi, cooperative medicinal effects with joint ingredients are achieved.

  Of the joint ingredients in the mixture, many of the fungicides and fungicides, bactericides, insecticides, acaricides, nematicides, biopesticides, pheromones, natural fungicides, and natural insecticides have been developed and marketed. Pesticide Handbook (2011) published by the Japanese Plant Protection Association, 2011 Agricultural Handbook (2011), National Agricultural Cooperative Federation Kumiai Agricultural Guide (2011), and SHIBYU INDEX issued by the Federation (2011).

  Examples are shown below, but are not limited thereto.

  Examples of bactericides include SH group enzyme inhibitory compounds, nucleic acid synthesis inhibitory active compounds, spindle yarn formation inhibitory active compounds, benzanilide compounds, strobilurin compounds, other electron transport inhibitory compounds, amino acid synthesis inhibitory active compounds, sterols Biosynthesis inhibitory active compounds, signal signal transduction inhibitory active compounds, lipid synthesis inhibitory active compounds, cell wall biosynthesis inhibitory active compounds, melanin synthesis inhibitory active compounds, host resistance-inducing compounds, other compounds with unclear effects, etc. be able to.

  SH group enzyme inhibitory active compounds: chlorothalonil, dithianon, captan, folpet, iminoctadine-albesilate, iminoctadine-triacetate, farbum ( ferbam), nabam, mancozeb, manneb, maneb, metiram, propineb, polycarbamate, thiram, zineb, ziram, oxidation Cupric oxide, cupric hydroxide, copper oxychloride, copper sulfate (anhydride), copper sulfate, sulfur, etc. .

  Nucleic acid synthesis inhibiting active compounds: metalaxyl, metalaxyl-M, oxadixyl, bupirimate, hymexazol, oxolinic acid and the like.

  Spindle yarn formation-inhibiting active compounds: benomyl, carbendazim, thiophanate-methyl, dietofencarb, zoxamide, pencycuron, fluopicolide and the like.

  Benzanilide compounds: flutolanil, mepronil, fluopyram, carboxin, oxycarboxin, thifluzamide, bixafen, fluxapyroxad, Furametpyr, isopyrazam, penflufen, penthiopyrad, sedaxane, boscalid and the like.

  Stravylline compounds: azoxystrobin, picoxystrobin, pyraoxystrobin, pyraclostrobin, pyrametostrobin, kresoxim-methyl, trif Roxystrobin, dimoxystrobin, metominostrobin, orysastrobin, famoxadone, fenamidone, pyribencarb, etc.

  Other compounds that inhibit electron transport system: diflumetorim, cyazofamid, amisulbrom, meptyldinocap, fluazinam, ferimzone, silthiofam, amethoctrazine etc.

  Amino acid synthesis inhibitory active compounds: cyprodinil, mepanipyrim, pyrimethanil, blasticidin-S, kasugamycin, streptomycin, oxytetracycline and the like.

  Sterol biosynthesis inhibiting active compounds: fenarimol, imazalil, oxpoconazole, pefurazoate, prochloraz, triflumizole, azaconazole, bitertanol ), Bromuconazole, cyproconazole, difenoconazole, epoxiconazole, fenbuconazole, flutriafol, hexaconazole, imicon Benconazole (imibenconazole), Metoconazole (metoconazole), Microbutanil (myclobutanil), Penconazole (propconazole), Cimeconazole (simeconazole), Tebuconazole (tebuconazole), Tetraconazole (triconon), Triimmephone (triimon) bird Dimenol, triticonazole, fenpropimorph, tridemorph, piperalin, spiroxamine, fenhexamid, pyributicarb, naphthifine Terbinafine, etc.

  Signal signal transduction inhibitory active compounds: quinoxyfen, proquinazid, fludioxonil, iprodione, procymidone, vinclozolin, myclozolin and the like.

  Lipid synthesis inhibitory active compounds: iprobenfos, isoprothiolane, quintozene, propamocarb, prothicarb and the like.

  Cell wall biosynthesis-inhibiting active compounds: validamycin, polyoxin B, dimethomorph, benthiavalicarb, iprovalicarb, valifenalate, mandipropamid, etc.

  Melanin synthesis inhibitory active compounds: pyroquilon, tricyclazole, carpropamid, diclocymet, fenoxanil and the like.

  Host resistance inducing compounds: acibenzolar-S-methyl, probenazole, isotianil, laminarin, etc.

  Other or unclear compounds: cymoxanil, fosetyl-Al, triazoxide, fursulfamide, methasulfocarb, ethaboxam, cyflufenamid, Metrafenone, pyriofenone, flutianil, ferimzone, chinomethionat, tebufloquin, pyridylamidine, enestroburin, flumorph, etc.

  Examples of insecticides / acaricides / nematicides include acetylcholinesterase inhibitor compounds, GABA-acting chloride channel inhibitor compounds, sodium ion channel inhibitor compounds, nicotinic acetylcholine receptor inhibitor compounds, chloride ion active compounds, Juvenile hormone analogues, non-selective inhibitory compounds, homozygous selective feeding inhibitory compounds, mite growth inhibitory compounds, microorganism-derived insect midgut membrane disruptors, ATP synthesis inhibitory compounds, oxidative phosphorylation uncoupling compounds Nicotinic acetylcholine receptor channel inhibitor compounds, chitin biosynthesis inhibitor compounds, molting / transformation inhibitor compounds, octopamine receptor agonist compounds, electron transport system inhibitor compounds, voltage-gated sodium channel inhibitor compounds, lipid synthesis inhibitor compounds, ryanodine receptor inhibitors Compound, other or unclear effect Compound, etc. can be mentioned.

  Acetylcholinesterase-inhibiting compounds: aldicarb, benfuracarb, carbaryl, carbofuran, carbosulfan, fenobucarb, methiocarb, methomyl, oxamyl ), Thiodicarb, acephate, cadusafos, chlorpyrifos, diazinon, dichlorvos, dimethoate, EPN, fenamiphos, fenitrothion, fenitrothion, fenitrothion (fosthiazate), imacyafos, malathion, methamidophos, monocrotophos, methylthalathion, parafenion, profenofos, terbufos and the like.

  GABA-acting chloride channel inhibitor compounds: endosulfan, ethiprole, fipronil, acetoprole and the like.

  Sodium ion channel blocking compounds: acrinathrin, allethrin, bifenthrin, lambda-cyhalothrin, cypermethrin, etofenprox, fenvalerate, permethrin (permethrin), DDT, methoxychlor, tefluthrin, etc.

  Nicotinic acetylcholine receptor inhibitor compounds: acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, etc. Spinetoram, spinosad, etc.

  Chloride ion channel active compounds: abamectin, emamectin benzoate, lepimectin, milbemectin and the like.

  Juvenile hormone analogs: kinoprene, methoprene, phenoxycarb, pyriproxyfen, etc.

  Non-selective inhibitory compounds: methyl bromide, chloropicrin, etc.

  Homogeneous selective feeding inhibitory compounds: pymetrozine, flonicamid, etc.

  Tick growth inhibitory compounds: clofentezine, hexythiazox, etoxazole, etc.

  Microbial-derived insect midgut lining destruction agent: Bacillus thuringiensis and the like.

  ATP synthesis inhibiting compounds: diafenthiuron, azocyclotin, cyhexatin, fenbutatin oxide, propargite, tetradifon, etc.

  Oxidative phosphorylation uncoupling compounds: chlorfenapyr and the like.

  Nicotinic acetylcholine receptor channel inhibitory compounds: bensultap, cartap hydrochloride, thiocyclam and the like.

  Chitin biosynthesis inhibiting compounds: chlorfluazuron, diflubenzuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron triflumuron, buprofezin, bistrifluron, noviflumuron and the like.

  Molting / metamorphosis inhibiting compounds: cyromazine, chromafenozide, halofenozide, methoxyfenozide, tebufenozide and the like.

  Octopamine receptor agonist compound: amitraz and the like.

  Electron transport inhibitor: hydramethylnon, acequinocyl, fluacrypyrim, fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tebufenpyrad, tebufenpyrad tolfenpyrad), rotenone, aluminum phosphide, cyenopyrafen, cyflumetofen and the like.

  Voltage-gated sodium channel inhibitor compounds: indoxacarb, metaflumizone, etc.

  Lipid synthesis inhibiting compounds: spirodiclofen, spiromesifen, spirotetramat and the like.

  Ryanodine receptor inhibitor compounds: chlorantraniliprole, cyantraniliprol, flubendiamide and the like.

  Other or unclear compounds: azadirachtin, benzoximate, bifenazate, chinomethionat, dicofol, pyridalyl, pyrifluquinazon, fluenesulfone fluensulfone) and the like.

  Examples of the herbicide include the following compounds.

  Lipid synthesis inhibitors: fluazifop-butyl, quizalofop-ethyl, cyhalofop-butyl, diclofop-methyl, fenoxaprop-P-ethyl -P-ethyl, alloxydim, sethoxydim, metamifop, esprocarb, prosulfocarb, pyributicarb, benfuresate, etofumesate and the like.

  Acetolactate synthase (ALS) inhibitors: amidosulfuron, azimsulfuron, bensulfuron-methyl, chlorimuron-ethyl, cinosulfuron, cyclosulfam Cyclosulfamuron, ethoxysulfuron, pyrazosulfuron-ethyl, foramsulfuron, imazosulfuron, iodosulfuron, chlorosulfuron, thiosulfuron・ Methyl (thifensulfuron-methyl), flazasulfuron (flazaslfuron), pyriminobac-methyl, florasulam, imazapyr, imazamox, imazaquin, imazaquin, mesosulfuron-methyl methyl), dimefuron, propoxycal Bazon (propoxycarbazone), full carbazone (flucarbazone), metosulam, penoxsulam, flucetosulfuron, bencarbazone, pyrimisulfan, pyroxsulam, ien azone Sulfamuron (orthosulfamuron), propyrisulfuron (metapysulfuron), metazosulfuron, etc.

  Photosynthesis electron transport system inhibitors: Simazine, metribuzin, amicarbazone, diuron, linuron, ioxynil, dimethametryn, phenmedipham, oxadiargyl (oxadiargyl), desmedipham, isoproturon, neburon, bromoxynil, methabenzthiazuron, metamitron, paraquat, diquat, Atrazine, flufenpyr-ethyl, bentazone, etc.

  Protox inhibitors: bifenox, lactofen, flumioxazin, carfentrazone-ethyl, pentoxazone, pyraclonil, pyraflufen- ethyl), oxadiazon, sulfentrazone, acifluorfen-sodium, fluthiacet-methyl and the like.

  4-HPPD inhibitors: mesotrione, isoxaflutole, benzofenap, benzobicyclon, topramezone, sulcotrione, tefyltrione ), Pyrasulfotole, pyrazoxifene, pyrazolate, and the like.

  Carotenoid biosynthesis inhibitors: aclonifen, flurtamone, diflufenican, fluridone, etc.

  EPSP synthase inhibitor: glyphosate and the like.

  Glutamate synthase inhibitors: glufosinate-ammonium, bialaphos, etc.

  Cell division inhibitor: oryzalin, pendimethalin, butamifos, carbetamide, triaziflam, flupoxam, dichlobenil, IPC (propham), trifluralin ), Cumyluron, indaziflam and the like.

  VLCFAs inhibitors: alachlor, metolachlor, tenenylchlor, mefenacet, fentrazamide, cafenstrole, pretilachlor, indanofan, anilofos Flufenacet, napropamide, dimethenamid, propisochlor, fenoxasulfone, ipfencarbazone and the like.

  Auxin-active herbicides: clomeprop, 2,4-D, MCPA, MCPB, MCPP, triclopyr, etc.

  Compounds with unknown activity: cinmethylin, bromobutide, daimuron, oxaziclomefone, etobenzanid, benthiocarb, pyroxasulfone, etc.

  Oxidative phosphorylation uncouplers: dinoterb, tribufos, ethephon, thidiazuron, cyclanilide, saflufenacil, isoxadifen, ethiozin and the like.

Examples of biological pesticides include
(1) Nuclear polyhedrosis virus (NPV), granulosis virus (GV), cytoplasmic polyhedrosis virus (CPV), etc.
(2) Steinernema carpocapsae, Steinernema glaseri, Monocrosporium phymatophagum, Steinernema kushidaie, Steinernema kushidaie etc.
(3) Agrobacterium radiobacter, Bacillus subtilis, Erwinia carotovora, Pseudomonas fluorescens, Talaromyces flavus, Talaromyces flavus, (Trichoderma atroviride) etc.
(4) Bacillus thuringiensis, Beauveria brongniartii, Beauveria bassiana, Paecilomyces fumosoroseus, Verticillium lecanii, nas Xest etc.
(5) Onsatsume wasp (Encarsia formosa), Sakutaku bee (Eretmocerus eremicus), Scarlet wasp (Eretmocerus mundus), Colleman's wasp (Aphidius colemani), Aphidoletes aphidimyzaly ), Dacnusa sibirica, Phytoseiulus persimilis, Amblyseius cucumeris, Amblyseius californicus, Orius strigicollis, etc.

  Examples of pheromone agents include: chodrelua ((E, E) -8,10-Dodecadien-1-ol), beet armorua B ((Z) -9-Tetradecen-1-ol), tetradodecenyl Examples thereof include acetate ((Z) -11-Tetradecenyl acetate), pyrimalua (14-Methyl-1-octadecene), and peach flua ((Z) -13-Eicosen-10-one).

  Examples of natural fungicides and pesticides include machine oils, methylphenyl acetate, α-pinene, protein hydrolysate, (Z) -1 -Tetradecen-1-ol, turpentine and the like.

Example 1
(1) In General Formula (I), A = 1,4-C ₆ H ₄ , B = H, R ¹ , R ² = —CH═CH—CH═CH—, R ³ = H, R ⁴ = H ( Table 1, Synthesis of Compound No. 1)
Stage A: 4-quinolinecarboxaldehyde oxime

To 600 mL of ethanol and 300 mL of water, 40.50 g of 4-quinolinecarboxaldehyde, 23.00 g of hydroxylamine hydrochloride and 31.40 g of sodium acetate were added, and the mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated, the residue was suspended in water, and the white solid was filtered. The solid was washed with water and dried under reduced pressure to obtain 42.57 g of an oxime compound.
Step B: 4- (Aminomethyl) quinoline

To 1.00 L of methanol, 50.00 g of the oxime compound obtained in the above step and 13.60 g of palladium carbon (palladium 10%, approximately 55% water-wet product) were added and stirred at room temperature for 1 hour under hydrogen pressure of 1 atm. The reaction solution was filtered through Celite, the organic layer was concentrated, and the residue was dried under reduced pressure to obtain 46.04 g of a quinoline compound.
Step C: 4-Iodo-N- (quinolin-4-ylmethyl) benzenesulfonamide

46.04 g of the quinoline compound obtained in the above step and 40.30 mL of triethylamine were added to 530 mL of dichloromethane, and the solution was cooled to 0 ° C. After cooling, 83.80 g of 4-iodobenzenesulfonyl chloride was added to the solution in several portions and stirred at room temperature for 2.5 hours. Water was added to the reaction solution, and the white solid was filtered. The solid was washed twice with water and once with dichloromethane and dried under reduced pressure to obtain 99.72 g of a sulfonamide compound.
Step D: N- (Quinolin-4-ylmethyl) -4-((trimethylsilyl) ethynyl) benzenesulfonamide

To 1.50 L of tetrahydrofuran was added 63.60 g of the sulfonamide compound obtained in the above step, 31.10 mL of trimethylsilylacetylene, 5.26 g of dichlorobis (triphenylphosphine) palladium, 1.43 g of copper iodide, 83.40 mL of triethylamine, and 70 Stir at 4 ° C. for 4 hours. The reaction was cooled to room temperature and filtered through celite. The filtrate was concentrated, water was added to the residue, and the mixture was extracted with chloroform. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and then dried over sodium sulfate. After filtering sodium sulfate, the organic layer was concentrated, the residue was suspended in diethyl ether, and the yellow solid was filtered. The solid was washed with diethyl ether and dried under reduced pressure to obtain 58.40 g of a trimethylsilyl compound.
Step E: 4-Ethynyl-N- (quinolin-4-ylmethyl) benzenesulfonamide

  To 250 mL of methanol were added 5.00 g of the trimethylsilyl compound obtained in the above step and 3.50 g of potassium carbonate, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was concentrated, water and 6N hydrochloric acid were added to the residue, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine and dried over sodium sulfate. After filtering sodium sulfate, the organic layer was concentrated, and the residue was dried under reduced pressure to obtain 3.17 g of an ethynyl compound.

  According to a similar production method, Table 1, Compound No. 2-4, 6-8, 11-16, 18-21, 23-28, 30-39, 41-45, 47-50, 52-55, 57-69, 71, 87, 97, 109-133 135-140, 142-156, 158, 160-164, 170-177 were synthesized.

  N- (2-ethynylphenyl) acetamide, N- (3-ethynylphenyl) acetamide, and N- (4-ethynylphenyl) acetamide are the corresponding anilines according to the method described in Patent Document 16 (US2004 / 87789). More manufactured. 4-ethynylbenzonitrile, 1- (difluoromethoxy) -4-ethynylbenzene, (4-ethynylphenyl) (methyl) sulfane, (4-ethynylphenyl) (trifluoromethyl) sulfane, 5-ethynyl-2,3- Dihydrobenzofuran, 1,4-dichloro-2-ethynylbenzene, 1,3-dichloro-2-ethynylbenzene, 2-chloro-1-ethynyl-4-fluorobenzene, 4-ethynylquinoline, 2-ethynylthiazole, 4- Ethinylthiazole, 5-ethynylthiazole, 4-ethynyl-1-methyl-1H-pyrazole, and 5-ethynyl-1-methyl-1H-pyrazole are based on the method described in Non-Patent Document 1 (Synlett, 1996, 521.). From the corresponding aldehyde. 1- (2-Ethynylphenyl) ethanone, 2,4-dichloro-1-ethynylbenzene, 1,3-dichloro-5-ethynylbenzene, 3-ethynylfuran and 2-ethynylthiophene are described in Non-Patent Document 2 (Journal of Organic). Chemistry, 1996, 61, 6906.) was prepared from the corresponding trimethylsilylacetylene. 2-Ethynylfuran was produced from the corresponding dibromoolefin according to the method described in Patent Document 17 (WO2009 / 111830). 2-Ethynyl-2-methyl-1,3-dioxolane and 2-ethynyl-2-methyl-1,3-dioxane are obtained by the method described in Non-Patent Document 3 (Journal of Organic Chemistry, 1998, 63, 1761.). According to the same manner, it was produced from 3-butyn-2-one. 1,1-dichloro-2-ethynylcyclopropane was prepared according to the method described in Non-Patent Document 4 (Zhurnal Organicheskoi Kimii, 1986, 22, 1195.), and then produced Non-Patent Document 5 (Synlett, 1996, 521.). 1,1-Dichloro-2-methyl-2-ethynylcyclopropane was produced from the corresponding enyne according to the method described in Non-Patent Document 6 (Zhurnal Organicheskoi Kimii, 1982, 18, 2295.). As other acetylenes, commercially available products were used.

(2) In general formula (I), A = 1,4-C ₆ H ₄ , B = 2-CH ₂ F—C ₆ H ₄ , R ¹ , R ² = —CH═CH—CH═CH—, R ³ = H, R ⁴ = H (Table 1, Synthesis of Compound No. 5)
Step A: 4-((2- (Fluoromethyl) phenyl) ethynyl) -N- (quinolin-4-ylmethyl) benzenesulfonamide

To 30.00 mL of dichloromethane was added Table 3, Compound No. 4 mg of the alcohol compound 4 and 200 μL of N, N-diethylaminosulfur trifluoride were added, and the mixture was stirred at room temperature for 1 hour. A saturated aqueous sodium hydrogen carbonate solution was added to the reaction solution, and the mixture was separated, extracted twice with dichloromethane, and the organic layer was dried over sodium sulfate. After filtering the sodium sulfate, the organic layer is concentrated, and the residue is purified by silica gel flash chromatography (eluted with ethyl acetate-hexane: 20% -80%) using a flash automatic purifier (Biotage AB / Isolera ^™ ). Gave 250 mg of fluoro compound.

  According to a similar production method, Table 1, Compound No. 165, 167, and 168 were synthesized.

(3) In the general formula (I), A = 1,4-C ₆ H ₄ , B = 2-CO ₂ CH ₃ —C ₆ H ₄ , R ¹ , R ² = —CH═CH—CH═CH—, R ³ = H, R ⁴ = H (Table 1, Synthesis of Compound No. 9)
Step A: methyl 2-((4- (N- (quinolin-4-ylmethyl) sulfamoyl) phenyl) ethynyl) benzoate

  To 6.00 mL of tetrahydrofuran was added Table 1, Compound No. 1 ethynyl compound (380 mg), methyl 2-iodobenzoate (464 mg), dichlorobis (triphenylphosphine) palladium (41 mg), copper iodide (11 mg) and triethylamine (660 μL) were added, and the mixture was stirred at 70 ° C. for 8 hours. The reaction mixture was cooled to room temperature, filtered through celite, and concentrated. Water was added to the residue and extracted with chloroform. The organic layer was washed with saturated brine and dried over sodium sulfate. After filtering sodium sulfate, the organic layer was concentrated, the residue was suspended in diethyl ether, and the solid was filtered. The solid was washed with diethyl ether and dried under reduced pressure to obtain 302 mg of methyl benzoate compound.

  According to a similar production method, Table 1, Compound No. 10, 17, 22, 29, 40, 46, 51, 56, 70, 72 to 86, 88 to 96, 98 to 108, 169 were synthesized.

  2-Fluoro-3-iodopyridine was produced from 2-fluoropyridine in accordance with the method described in Non-Patent Document 7 (Tetrahedron, 1993, 49, 49.). 2-Fluoro-4-iodopyridine was produced from 2-fluoro-3-iodopyridine according to the method described in Non-Patent Document 8 (Journal of Organic Chemistry, 1993, 58, 7832.). 3-Iodo-2-methoxypyridine and 4-iodo-2-methoxypyridine were produced from the corresponding fluoropyridines according to the method described in Patent Document 18 (WO2008 / 25509). As other aryl halides, commercially available products were used.

(4) In general formula (I), A = 1,4-C ₆ H ₄ , B = CHO, R ¹ , R ² = —CH═CH—CH═CH—, R ³ = H, R ⁴ = H ( Table 1, Synthesis of Compound No. 134)
Step A: 4- (3-Oxo-1-propynyl) -N- (quinolin-4-ylmethyl) benzenesulfonamide

  In 34.00 mL of water, Table 1, Compound No. 2.87 g of 153 acetal compound and 67.00 mL of trifluoroacetic acid were added, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated, saturated aqueous sodium hydrogen carbonate solution was added to the residue, and the mixture was extracted with 10% methanol-chloroform. The organic layer was dried over sodium sulfate and the sodium sulfate was filtered. The organic layer was concentrated, the residue was suspended in diethyl ether, and the brown solid was filtered. The solid was washed with diethyl ether and dried under reduced pressure to obtain 2.08 g of an aldehyde compound.

  According to a similar production method, Table 1, Compound No. 141 was synthesized.

(5) In the general formula (I), A = 1,4-C ₆ H ₄ , B = CONHCH ₃ , R ¹ , R ² = —CH═CH—CH = CH—, R ³ = H, R ⁴ = H (Table 1, Synthesis of Compound No. 157)
Step A: N-methyl-3- (4- (N- (quinolin-4-ylmethyl) sulfamoyl) phenyl) propiolamido

Add 15.00 mL of tetrahydrofuran to Table 1. 400 mg of 156 ester compound and 2.00 mL of 40% methylamine-methanol solution were added, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated, and the residue was purified by flash chromatography on silica gel (ethyl acetate-hexane: 30% -100% followed by methanol-chloroform: 15%) using a flash automatic purifier (Biotage AB / Isolera ^™ ). As a result, 75 mg of an amide compound was obtained.

(6) In the general formula (I), A = 1,4-C ₆ H ₄ , B = C (= NOCH ₃ ) CH ₃ , R ¹ , R ² = —CH═CH—CH═CH—, R ³ = H, R ⁴ = H (Table 1, Synthesis of Compound No. 159)
Step A: 4- (3- (methoxyimino) -1-butynyl) -N- (quinolin-4-ylmethyl) benzenesulfonamide

  In Table 1, No. 1 in 10.00 mL of methanol. 141 ketone compound (500 mg), O-methylhydroxylamine hydrochloride (230 mg), sodium sulfate (390 mg) and pyridine (1.60 mL) were added, and the mixture was stirred at room temperature for 30 minutes. Water was added to the reaction mixture, and the mixture was extracted twice with ethyl acetate. The organic layer was washed twice with water and once with saturated brine, and then dried over magnesium sulfate. After filtering the magnesium sulfate, the organic layer is concentrated, and the residue is purified by silica gel flash chromatography (eluted with ethyl acetate-toluene: 50%) to obtain 410 mg of the oxime compound as an isomer mixture of cis: trans = 4: 6. Got as.

(7) In General Formula (I), A = 1,4-C ₆ H ₄ , B = CHF ₂ , R ¹ , R ² = —CH═CH—CH═CH—, R ³ = H, R ⁴ = H (Table 1, Synthesis of Compound No. 166)
Step A: 4- (3,3-Difluoro-1-propynyl) -N- (quinolin-4-ylmethyl) benzenesulfonamide

In Table 1, No. 1 in 10.00 mL of dichloromethane. 134 mg of aldehyde compound 134 and 198 μL of N, N-diethylaminosulfur trifluoride were added, and the mixture was stirred at room temperature for 4 hours. A saturated aqueous sodium hydrogen carbonate solution, water and methanol were added to the reaction solution, and the mixture was separated, and the organic layer was dried over sodium sulfate. After filtering sodium sulfate, the organic layer is concentrated, and the residue is purified by silica gel flash chromatography (elution with ethyl acetate-hexane: 50% -100%) using a flash automatic purifier (Biotage AB / Isolera ^™ ). Gave 35 mg of difluoro compound.

(8) In the general formula (I), A = 2-CH ₃ -1,4-C ₆ H ₄ , B = C ₆ H ₅ , R ¹ , R ² = —CH═CH—CH═CH—, R ³ = H, R ⁴ = H (Table 1, Synthesis of Compound No. 178)
Step A: 4-Bromo-2-methyl-N- (quinolin-4-ylmethyl) benzenesulfonamide

Table 1, Compound No. In Step C of Synthesis 1, the sulfonamide compound was obtained by using 4-bromo-2-methylbenzenesulfonyl chloride instead of 4-iodobenzenesulfonyl chloride.
Step B: 2-Methyl-4- (phenylethynyl) -N- (quinolin-4-ylmethyl) benzenesulfonamide

  Table 1, Compound No. In step D of the synthesis of 1, the sulfonamide compound obtained in the above step in place of 4-iodo-N- (quinolin-4-ylmethyl) benzenesulfonamide, phenylacetylene instead of trimethylsilylacetylene, 1, compound no. 178 was synthesized.

  According to a similar production method, Table 1, Compound No. 179-214 were synthesized.

  5-bromopyridine-2-sulfonyl chloride, 6-bromopyridine-3-sulfonyl chloride, 5-bromofuran-2-sulfonyl chloride, 4-bromothiophene-2-sulfonyl chloride, 5-bromothiazole-2-sulfonyl chloride Was prepared from the corresponding dihaloheterocyclic compound according to the method described in Non-Patent Document 9 (Synlett, 2011, (8), 1117.). 2-Chloropyrimidine-5-sulfonyl chloride was produced from 2-aminopyrimidine according to the method described in Patent Document 19 (WO 2006/29154). 3-Bromothiophene-2-sulfonyl chloride was produced from 3-bromothiophene according to the method described in Patent Document 20 (WO2004 / 074238). Commercially available products were used for the other sulfonyl chlorides.

(9) In general formula (I), A = 2,4-thiazole, B = C ₆ H ₅ , R ¹ , R ² = —CH═CH—CH═CH—, R ³ = H, R ⁴ = H ( Table 1, Synthesis of Compound No. 215)
Step A: 4-Bromo-2- (phenylethynyl) thiazole

Table 1, Compound No. In the synthesis step D of 1, an ethynyl compound was obtained by using 2,4-dibromothiazole instead of 4-iodo-N- (quinolin-4-ylmethyl) benzenesulfonamide and phenylacetylene instead of trimethylsilylacetylene. It was.
Step B: 2- (Phenylethynyl) thiazole-4-sulfonyl chloride

A sulfonyl chloride compound was obtained from the ethynyl compound obtained in the above step according to the method described in Non-Patent Document 9 (Synlett, 2011, (8), 1117.).
Step C: 2- (Phenylethynyl) -N- (quinolin-4-ylmethyl) thiazole-4-sulfonamide

  Table 1, Compound No. In step C of the synthesis of compound No. 1, by using the sulfonyl chloride compound obtained in the above step in place of 4-iodobenzenesulfonyl chloride, Table 1, Compound No. 215 was obtained.

  According to a similar production method, Table 1, Compound No. 216,217 were synthesized.

(10) In the general formula (I), A = 1,4-C ₆ H ₄ , B = C ₆ H ₅ , R ¹ , R ² = -CH = CH-CH = CH-, R ³ = H, R ⁴ = Cl (Table 1, Synthesis of Compound No. 218)
Step A: 4- (Bromomethyl) -2-chloroquinoline

To 25.00 mL of carbon tetrachloride, 2.00 g of 2-chloro-4-methylquinoline, 2.16 g of N-bromosuccinimide and 183 mg of azobisisobutyronitrile were added and stirred at 80 ° C. for 6 hours. The reaction mixture was cooled to room temperature, water was added, and the mixture was extracted with chloroform. The organic layer was dried over sodium sulfate, sodium sulfate was filtered off, and the organic layer was concentrated to obtain 2.33 g of bromomethyl compound as a 2: 1 mixture with the raw material.
Step B: 4- (azidomethyl) -2-chloroquinoline

To 15.00 mL of N, N-dimethylformamide were added 1.65 g of the bromomethyl compound obtained in the above step and 580 mg of sodium azide, and the mixture was stirred at 60 ° C. The reaction mixture was concentrated, water was added to the residue, and the mixture was extracted with chloroform. The organic layer was dried over sodium sulfate, sodium sulfate was filtered off, and the organic layer was concentrated to obtain 1.35 g of an azide compound.
Step C: (2-Chloroquinolin-4-yl) methanamine

1.35 g of the azide compound obtained in the above step and 1.94 g of triphenylphosphine were added to 30.00 mL of tetrahydrofuran and 3.00 mL of water, and the mixture was stirred overnight at room temperature. The reaction solution was concentrated, and the residue was purified by silica gel flash chromatography (eluted with methanol-chloroform) using a flash automatic purifier (manufactured by Biotage AB / Isolera ^™ ) to obtain 220 mg of a methanamine compound.
Step D: N-((2-chloroquinolin-4-yl) methyl) -4-iodobenzenesulfonamide

Table 1, Compound No. In Step 1 of the synthesis of 1, the sulfonamide compound was obtained by using the methanamine compound obtained in the above step instead of 4- (aminomethyl) quinoline.
Step E: N-((2-chloroquinolin-4-yl) methyl) -4- (phenylethynyl) benzenesulfonamide

  Table 1, Compound No. In step D of the synthesis of 1, the sulfonamide compound obtained in the above step in place of 4-iodo-N- (quinolin-4-ylmethyl) benzenesulfonamide, phenylacetylene instead of trimethylsilylacetylene, 1, compound no. 218 was obtained.

(11) In general formula (I), A = 1,4-C ₆ H ₄ , B = H, R ¹ = H, R ² = H, R ³ = H, R ⁴ = H (Table 1, Compound No. 1). 219)
Step A: 4-Iodo-N- (pyridin-4-ylmethyl) benzenesulfonamide

Table 1, Compound No. In Step C of Synthesis 1, the sulfonamide compound was obtained by using 4-picolylamine instead of 4- (aminomethyl) quinoline.
Step B: N- (Pyridin-4-ylmethyl) -4-((trimethylsilyl) ethynyl) benzenesulfonamide

Table 1, Compound No. In Step D of Synthesis 1, the trimethylsilyl compound was obtained by using the sulfonamide compound obtained in the above step instead of 4-iodo-N- (quinolin-4-ylmethyl) benzenesulfonamide.
Step C: 4-Ethynyl-N- (pyridin-4-ylmethyl) benzenesulfonamide

  Table 1, Compound No. In the synthesis stage E of Table 1, using the trimethylsilyl compound obtained in the above stage instead of N- (quinolin-4-ylmethyl) -4-((trimethylsilyl) ethynyl) benzenesulfonamide, Table 1, Compound No. . 219 was obtained.

  According to a similar production method, Table 1, Compound No. 220-222,224-226,231-239,243-252,254-263,267,268,272,275-283,288-303,305-308,310,311,316,319-320 were synthesized .

(12) In General Formula (I), A = 1,4-C ₆ H ₄ , B = 2-CH ₂ F—C ₆ H ₄ , R ¹ = H, R ² = H, R ³ = H, R ⁴ = H (Table 1, Synthesis of Compound No. 223)
Step A: 4-((2- (Fluoromethyl) phenyl) ethynyl) -N- (pyridin-4-ylmethyl) benzenesulfonamide

  Table 1, Compound No. In step A of the synthesis of compound no. In place of Compound No. 4 222, Table 1, Compound No. 223 was obtained.

  According to a similar production method, Table 1, Compound No. 317 and 318 were synthesized.

(13) In general formula (I), A = 1,4-C ₆ H ₄ , B = 2-CO ₂ H—C ₆ H ₄ , R ¹ = H, R ² = H, R ³ = H, R ⁴ = H (Synthesis of Table 1, Compound No. 227)
Step A: 2-((4- (N- (pyridin-4-ylmethyl) sulfamoyl) phenyl) ethynyl) benzoic acid

  Table 1, Compound No. In synthesis step A of compound 9, compound no. In place of Compound No. 1 219 by using 2-iodobenzoic acid instead of methyl 2-iodobenzoate, respectively. 227 was obtained.

  According to a similar production method, Table 1, Compound No. 228-230, 240-242, 253, 264-266, 269-271, 274, 284-287 were synthesized.

(14) In general formula (I), A = 1,4-C ₆ H ₄ , B = — (C═O) NH—CH═CH—CH═C—, R ¹ = H, R ² = H, R ³ = H, R ⁴ = H (Table 1, Synthesis of Compound No. 273)
Step A: 4-((2-oxo-1,2-dihydropyridin-3-yl) ethynyl) -N- (pyridin-4-ylmethyl) benzenesulfonamide

In 10.00 mL of 1,4-dioxane, Table 1, Compound No. 734 mg of 271 fluoropyridine compound and 10.00 mL of 6N hydrochloric acid were added, and the mixture was stirred at 110 ° C. for 9 hours. To the reaction solution, 100 mL of a saturated aqueous sodium hydrogen carbonate solution, 2.40 g of sodium hydroxide and 100 mL of water were added to make the solution basic. After extracting twice with 10% methanol-chloroform, the organic layer was dried over sodium sulfate. After filtering sodium sulfate, the organic layer was concentrated, and the residue was purified by silica gel flash chromatography (elution with methanol-chloroform: 2% -20%) using a flash automatic purifier (Biotage AB / Isolera ^™ ). Table 1, Compound No. 273 was obtained.

(15) In general formula (I), A = 1,4-C ₆ H ₄ , B = (S) —CH (OH) CH ₂ OH, R ¹ = H, R ² = H, R ³ = H, R ⁴ = H (Synthesis of Table 1, Compound No. 304)
Step A: (S) -4- (3,4-Dihydroxy-1-butyn-1-yl) -N- (pyridin-4-ylmethyl) benzenesulfonamide

  To 7.00 mL of 1,4-dioxane, Table 1, Compound No. 506 mg of an acetonide compound of 305, 7.00 mL of 1N hydrochloric acid were added, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated, 50 mL of a saturated aqueous sodium hydrogen carbonate solution and 10% methanol-chloroform were added to the residue, and an off-white solid was filtered. The solid was washed with chloroform and water and dried under reduced pressure to give Table 1, Compound No. 304 was obtained.

(16) In general formula (I), A = 1,4-C ₆ H ₄ , B = CO ₂ Et, R ¹ = H, R ² = H, R ³ = H, R ⁴ = H (Table 1, Compound) Synthesis of No. 309)
Stage A: tert-Butyl (4-iodophenyl) sulfonyl (pyridin-4-ylmethyl) carbamate

To 100 mL of acetonitrile, 4.00 g of 4-iodo-N- (pyridin-4-ylmethyl) benzenesulfonamide, 2.77 g of di-tert-butyl dicarbonate and 650 mg of N, N-dimethyl-4-aminopyridine were added at room temperature. Stir for 4 hours. Water was added to the reaction solution, and the white solid was filtered. The solid was washed with water and dried under reduced pressure to obtain a carbamic acid compound.
Step B: Ethyl 3- (4- (N- (tert-butoxycarbonyl) -N- (pyridin-4-ylmethyl) sulfamoyl) phenyl) propiolate

Table 1, Compound No. In step D of the synthesis of 1, the carbamate compound obtained in the above step was used in place of 4-iodo-N- (quinolin-4-ylmethyl) benzenesulfonamide, and ethyl propiolate was used in place of trimethylsilylacetylene. A propiolic acid compound was obtained.
Step C: Ethyl 3- (4- (N- (pyridin-4-ylmethyl) sulfamoyl) phenyl) propiolate

The propiolic acid compound obtained in the above step and 10 mL of trifluoroacetic acid were added to 10 mL of methylene chloride, and the mixture was stirred at room temperature for 1.5 hours. The reaction solution was concentrated, and the residue was purified by silica gel flash chromatography (eluted with methanol-chloroform) using a flash automatic purification apparatus (Biotage AB / Isolera ^™ ). 309 was obtained.

(17) In general formula (I), A = 1,4-C ₆ H ₄ , B = C (= NOCH ₃ ) CH ₃ , R ¹ = H, R ² = H, R ³ = H, R ⁴ = H (Table 1, Synthesis of Compound No. 312)
Step A: 4- (3- (methoxyimino) -1-butyn-1-yl) -N- (pyridin-4-ylmethyl) benzenesulfonamide

  Table 1, Compound No. In step A of the synthesis of 159, no. 141, using the corresponding pyridine compound in place of the quinoline compound of Table 1, compound No. 312 was obtained.

  According to a similar production method, Table 1, Compound No. 313 to 315 were synthesized.

(18) In the general formula (I), A = 1,3-C ₆ H ₄ , B = C ₆ H ₅ , R ¹ = H, R ² = H, R ³ = H, R ⁴ = H (Table 1, Synthesis of Compound No. 321)
Step A: 3-Bromo-N- (pyridin-4-ylmethyl) benzenesulfonamide

Table 1, Compound No. In Step C of Synthesis 1, a sulfonamide compound was obtained by using 3-bromobenzenesulfonyl chloride instead of 4-iodobenzenesulfonyl chloride and 4-picolylamine instead of 4- (aminomethyl) quinoline. .
Step B: 3- (Phenylethynyl) -N- (pyridin-4-ylmethyl) benzenesulfonamide

  Table 1, Compound No. In step D of the synthesis of 1, using the sulfonamide compound obtained in the above step in place of 4-iodo-N- (quinolin-4-ylmethyl) benzenesulfonamide, and using phenylacetylene instead of trimethylsilylacetylene, Table 1, Compound No. 321 was synthesized.

  According to a similar production method, Table 1, Compound No. 322 to 343, 347 were synthesized.

(19) In general formula (I), A = 2,4-thiazole, B = C ₆ H ₅ , R ¹ = H, R ² = H, R ³ = H, R ⁴ = H (Table 1, Compound No. 1). 346)
Step A: 2- (Phenylethynyl) -N- (pyridin-4-ylmethyl) thiazole-4-sulfonamide

  Table 1, Compound No. In step C of the synthesis of 215, by using 4-picolylamine instead of 4- (aminomethyl) quinoline, Table 1, Compound No. 346 was obtained.

  According to a similar production method, Table 1, Compound No. 344, 345, and 348 were synthesized.

  1- (Phenylethynyl) -1H-pyrazole-4-sulfonyl chloride According to the method described in Non-Patent Document 12 (Synthesis, 2011, (5), 816.), 1- (phenylethynyl) -1H-pyrazole Was manufactured according to the method described in Non-Patent Document 13 (Journal of chemical Society (C), 1968, 1120.).

(9) In the general formula (I), A = 1,4-C ₆ H ₄ , B = C ₆ H ₅ , R ¹ = H, R ² = C ₆ H ₅ , R ³ = H, R ⁴ = H ( Table 1, Synthesis of Compound No. 349)
Stage A: (2-Phenylpyridin-4-yl) methanol

To 20.00 mL of 1,4-dioxane, 1.0 g of (2-bromopyridin-4-yl) methanol, 778 mg of phenylboronic acid, 307 mg of tetrakis (triphenylphosphine) palladium, and 10.00 mL of a saturated aqueous sodium carbonate solution were added, and 100 ° C. Stir with. The reaction was cooled to room temperature and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over sodium sulfate. After filtering sodium sulfate, the organic layer was concentrated, and the residue was purified by silica gel flash chromatography (eluted with ethyl acetate-hexane) with a flash automatic purifier (Biotage AB / Isolera ^™ ) to obtain 940 mg of phenyl compound. Obtained.
Step B: 4- (azidomethyl) -2-phenylpyridine

To 10.00 mL of tetrahydrofuran was added 920 mg of the phenyl compound obtained in the above step, and the solution was cooled to 0 ° C. After cooling, 1.70 g of 2-azido-1,3-dimethylimidazolinium hexafluorophosphate and 964 μL of 1,8-diazabicyclo [5.4.0] undec-7-ene were added to this solution, and the mixture was stirred at room temperature for 1 hour. Stir. Water was added to the reaction solution and concentrated. Water was added to the residue and extracted with dichloromethane. The organic layer was dried over sodium sulfate, the sodium sulfate was filtered, the organic layer was concentrated, and the residue was subjected to silica gel flash chromatography (eluted with ethyl acetate-hexane) using a flash automatic purifier (Biotage AB / Isolera ^™ ). By purification, 980 mg of an azide compound was obtained.
Step C: (2-Phenylpyridin-4-yl) methanamine

To 10.00 mL of tetrahydrofuran and 1.00 mL of water were added 980 mg of the azide compound obtained in the above step and 1.47 g of triphenylphosphine, and the mixture was stirred at room temperature for 5 hours. The reaction solution was concentrated, and the residue was purified by silica gel flash chromatography (eluted with methanol-chloroform) using a flash automatic purifier (Biotage AB / Isolera ^™ ) to obtain 800 mg of a methanamine compound.
Step D: 4-Iodo-N-((2-phenylpyridin-4-yl) methyl) benzenesulfonamide

Table 1, Compound No. In Step 1 of the synthesis of 1, the sulfonamide compound was obtained by using the methanamine compound obtained in the above step instead of 4- (aminomethyl) quinoline.
Step E: 4- (Phenylethynyl) -N-((2-phenylpyridin-4-yl) methyl) benzenesulfonamide

  Table 1, Compound No. In step D of the synthesis of 1, the sulfonamide compound obtained in the above step in place of 4-iodo-N- (quinolin-4-ylmethyl) benzenesulfonamide, phenylacetylene instead of trimethylsilylacetylene, 1, compound no. 349 was obtained.

  According to a similar production method, Table 1, Compound No. 350-359 and 361-364 were synthesized.

  4- (Aminomethyl) picolinonitrile was produced from the corresponding methylpyridine according to the method described in Non-Patent Document 10 (Bioorganic & Medicinal Chemistry, 2005, 13, 4022.). (2-Fluoropyridin-4-yl) methanamine was produced from the corresponding bromomethylpyridine according to the method described in Patent Document 21 (WO2005 / 80350). (3-Fluoropyridin-4-yl) methanamine was produced from the corresponding pyridinecarbaldehyde according to the method described in Patent Document 22 (WO2009 / 57827). (3-Chloropyridin-4-yl) methanamine was produced according to the method described above after producing the corresponding methanol according to the method described in Patent Document 25 (WO2010 / 132999). (2-Chloro-6-methylpyridin-4-yl) methanamine and (2,6-dichloropyridin-4-yl) methanamine are according to the method described in Non-Patent Document 11 (Tetrahedron, 2007, 63, 291). After the corresponding methanol was produced, it was produced according to the method described above. (3,5-dichloropyridin-4-yl) methanamine was prepared from the corresponding pyridinecarbaldehyde according to the method described in Patent Document 25 (WO2005 / 116209). As other aminomethylpyridines, commercially available products were used.

(21) In the general formula (I), A = 1,4-C ₆ H ₄ , B = C ₆ H ₅ , R ¹ = H, R ² = tert-C ₄ H ₉ , R ³ = H, R ⁴ = tert-C ₄ H ₉ (Table 1, Synthesis of Compound No. 360)
Step A: 4- (Bromomethyl) -2,6-di-tert-butylpyridine

To 50.00 mL of carbon tetrachloride, 5.00 g of 2,6-di-tert-butyl-4-methylpyridine, 4.67 g of N-bromosuccinimide, and 800 mg of azobisisobutyronitrile were added and stirred at 60 ° C. for 7 hours. . The reaction mixture was cooled to room temperature, water was added, and the mixture was extracted with chloroform. The organic layer was dried over sodium sulfate, and after filtering the sodium sulfate, the organic layer was concentrated, and the residue was purified by silica gel flash chromatography using a flash automatic purifier (Biotage AB / Isolera ^™ ) to obtain bromomethyl compound 0. .96 g was obtained.

Step B: 4- (azidomethyl) -2,6-di-tert-butylpyridine

To 5.00 mL of N, N-dimethylformamide were added 0.95 g of the bromomethyl compound obtained in the above step and 326 mg of sodium azide, and the mixture was stirred at 70 ° C. The reaction mixture was concentrated, water was added to the residue, and the mixture was extracted with chloroform. The organic layer was dried over sodium sulfate, sodium sulfate was filtered off, and the organic layer was concentrated to obtain 810 mg of an azide compound.
Step C: (2,6-di-tert-butylpyridin-4-yl) methanamine

Table 1, Compound No. In Step C of Synthesis of 349, a methanamine compound was obtained by using the azide compound obtained in the above step instead of 4- (azidomethyl) -2-phenylpyridine.
Step D: N-((2,6-di-tert-butylpyridin-4-yl) methyl) -4-iodobenzenesulfonamide

Table 1, Compound No. In Step 1 of the synthesis of 1, the sulfonamide compound was obtained by using the methanamine compound obtained in the above step instead of 4- (aminomethyl) quinoline.
Step E: N-((2,6-di-tert-butylpyridin-4-yl) methyl) -4- (phenylethynyl) benzenesulfonamide

  Table 1, Compound No. In step D of the synthesis of 1, the sulfonamide compound obtained in the above step in place of 4-iodo-N- (quinolin-4-ylmethyl) benzenesulfonamide, phenylacetylene instead of trimethylsilylacetylene, 1, compound no. 360 was obtained.

  The compound [I] synthesized as described above, their physical properties and NMR data are shown in Table 1 (Table 1-1 to Table 1-46). In this specification, “Table 1” is a generic name (generic name) of Table 1-1 to Table 1-46.

Example 2 [Formulation example]
Formulation Example 1: Emulsion 10 parts of the compound of the present invention was dissolved in 45 parts of 1,2-dimethyl-4-ethylbenzene and 35 parts of 1-methyl-2-pyrrolidinone, and this was dissolved in Solpol 3005X (an interface manufactured by Toho Chemical Co., Ltd.). 10 parts of an activator (trade name) was added and mixed by stirring to obtain a 10% emulsion.
Formulation example 2: wettable powder 10 parts of the compound of the present invention was added to a mixture of 2 parts of sodium lauryl sulfate, 4 parts of sodium lignin sulfonate, 20 parts of white carbon and 64 parts of clay. % Wettable powder was obtained.
Formulation Example 3: Granules To 5 parts of the present compound, 2 parts of sodium dodecylbenzenesulfonate, 2 parts of carboxymethylcellulose, 2 parts of sodium lauryl sulfate, 10 parts of bentonite and 79 parts of clay were added and mixed thoroughly. An appropriate amount of water was added and the mixture was further stirred, granulated with a granulator, and dried by ventilation to obtain a 5% granule.
Formulation Example 4: Powder 1 part of the original compound is dissolved in 2 parts of soybean oil, 5 parts of white carbon, 0.3 part of isopropyl acid phosphate (PAP) and 91.7 parts of clay are added, and the mixture is stirred and mixed with a juice mixer. A 1% powder was obtained.
Formulation Example 5: Flowable agent 20 parts of water containing 20 parts of the present compound and 2 parts, 1 part and 0.2 part of polyoxyethylene alkyl ether, sodium dialkylsulfosuccinate and 1,2-benzisothiazolin-3-one, respectively Were mixed with 60 parts of water containing 8 parts and 0.32 parts of propylene glycol and xanthan gum, respectively, to obtain a 20% suspension in water.
Formulation Example 6: Granule wettable powder 2 parts of sodium lauryl sulfate, 3 parts of sodium alkylnaphthalene sulfonate, 5 parts of dextrin, 20 parts of white carbon and 50 parts of clay were added to 20 parts of the compound of the present invention and mixed thoroughly. An appropriate amount of water was added, and the mixture was further stirred, granulated with a granulator, and dried by ventilation to obtain a 20% granular wettable powder.

Example 3 [Efficacy test]
(1) Control effect test against tomato plague A potted tomato (variety; large-scale longevity, 5.5 leaf stage) is a chemical solution in which 10% wettable powder of each test compound is adjusted to 125 ppm (hereinafter referred to as a reagent solution). Sprayed with 15 ml per pot using a spray gun, sprayed with a zoospore suspension (Phytophthora infestans) zoospore suspension (sporemide concentration of 1.0 × 10 ⁴ cells / ml) one day later, wet at 21 ° C. After standing for 1 day under room conditions and further in a greenhouse for 3 days to cause sufficient disease, the degree of disease on each leaf was examined, and the control value was calculated using the following formula.
Control value calculation; control value = {(untreated disease area rate−treated drug disease rate) / untreated disease area rate} × 100
The calculated control value was determined according to the following criteria. The results are shown in Table 2.
Control effect judgment A: 100% ≧ control value ≧ 60%
Control effect judgment B: 60%> control value ≧ 0%

(2) Control effect test for cucumber downy mildew Potato cucumber (variety; Sagamihanjiro, 2.5 leaf stage) 10% wettable powder of each test compound adjusted to 125 ppm (hereinafter referred to as reagent solution and Sprayed 15 ml per pot using a spray gun, and one day later sprayed with a zoosporangium suspension of Pseudoperonospora cubensis (concentration of zoospore sac 1.0 × 10 ⁴ / ml) did. After inoculation, leave under a humid chamber condition at 21 ° C. for 1 day, and after leaving it in a greenhouse for 3 days to cause sufficient disease, the degree of disease on each leaf is compared with that of the untreated group, and the control effect is the same as in Example 1. Judgment was made. The results are shown in Table 3.

(3) Control effect test for cucumber powdery mildew Potted cucumber (variety; Sagamihanjiro, 2.0 leaf stage) 10% wettable powder of each test compound adjusted to 125 ppm (hereinafter referred to as reagent solution and 15 ml per pot using a spray gun, and one day later, a conidia suspension (conidia concentration of 1.0 × 10 ⁵ cells / ml) of Sphaerotheca cucurbitae was spray-inoculated. After sufficient disease was established in a greenhouse for 14 days, the degree of disease on each leaf was compared with the untreated group, and the control effect was determined in the same manner as in Example 1. The results are shown in Table 4.

(4) Efficacy test against cotton aphids Place a 3 cm diameter cucumber leaf piece on a moist sponge in a plastic cup, release 5 adult cotton aphids (Aphis gossypii), leave them overnight, and then lay larvae Numbers were counted. 0.4 ml of a chemical solution prepared by diluting a 10% wettable powder of the compounds shown in Table 1 to 250 ppm was sprayed, and the number of dead insects was investigated two days later to calculate the mortality rate. A mortality rate of 50% or more was determined as A, and a mortality rate of less than 50% was determined as B. The results are shown in Table 5.

(5) Efficacy test against Spodoptera litura 3 cm diameter Chinese cabbage leaf pieces were immersed in a chemical solution prepared by diluting 10% wettable powder of the compounds shown in Table 1 to 250 ppm, then air-dried, housed in a plastic petri dish, and Spodptera litura ) 10 1st instar larvae were released. The mortality was calculated by examining the number of dead worms two days after treatment. A mortality rate of 50% or more was determined as A, and a mortality rate of less than 50% was determined as B. The results are shown in Table 6.

Since the novel compound of the present invention represented by the formula [I] exhibits an excellent control activity against pests such as pathogens, insects, mites, nematodes and the like that particularly affect agricultural and horticultural plants, it is extremely useful as a new agricultural chemical. It is.

Claims (19)

Formula [I]:

[Wherein R ¹ , R ² , R ³ , R ⁴ are a hydrogen atom, —C (O) OR, —C (O) R, —R, —OR, —SR, —SO ₂ R, —OC, respectively. (O) R, —C (O) NHR, —C (O) NR ₂ , —NHSO ₂ R, —NRSO ₂ R, —NHR, —NR ₂ , —NHC (O) R, —NRC (O) R , —NHC (O) OR, —NRC (O) OR, —N (OR) C (O) OR, —NHSO ₂ R, —NRSO ₂ R, —SO ₂ NHR, —SO ₂ NR ₂ (where R is linear or branched alkyl having 1 to 8 carbon atoms, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms. or cycloalkyl or cycloalkenyl having 3 to 8 carbon atoms carbon atoms ^{3~8), - SiR 5 R 6} R 7, -OS iR ⁵ R ⁶ R ⁷ (R ⁵ , R ⁶ , R ⁷ is linear or branched alkyl or phenyl having 1 to 6 carbon atoms, and two or all of them may be the same or different substituents. Good), haloalkyl, haloalkenyl, haloalkoxy, acylalkoxy, acyloxyalkyl, alkylsulfonylalkyl, siloxyalkyl, hydroxyalkyl, alkoxyalkyl, haloalkoxyalkyl, alkylthioalkyl, dialkoxyacetal, alkoxyalkoxy, cyanoalkyl, halogen, cyano , Nitro, amino, hydroxy, pentahalosulfanyl, benzyl, benzyloxy, phenyl, phenoxy, pyridyl, oxazolyl, furyl, thiazolyl, naphthyl, pyrimidinyl, thienyl, benzothiazolyl, benzoo Sazoriru, Benzookisoriru, imide, formyl (-CHO), a carboxyl (-COOH) or thiophene ring to form together with the carbon atoms on the pyridine with ^{R 1} and ^{R 2} bond ring, pyridine ring, pyrrole ring, an imidazole ring, a benzene Represents a ring, naphthalene ring, pyrimidine ring, furan ring, pyrazine ring, pyrazole ring, oxazole ring,
A is phenylene, 5- or 6-membered heteroarrangeyl (heteroarene contains 1-3 N, O, S atoms in the ring, and both phenylene and heteroarrangeyl are -C (O) OR _{, -C (O) R, -R} , -OR, -SR, -SO 2 R, -OC (O) R, -C (O) NHR, -C (O) NR 2, -NHSO 2 R, - _{NRSO 2 R, -NHR, -NR 2} , -NHC (O) R, -NRC (O) R, -NHC (O) OR, -NRC (O) OR, -N (OR) C (O) OR, —NHSO ₂ R, —NRSO ₂ R, —SO ₂ NHR, —SO ₂ NR ₂ (wherein R is linear or branched alkyl having 1 to 8 carbon atoms, and having 2 to 8 carbon atoms) Linear or branched alkenyl, linear or branched alkynyl having 2 to 8 carbon atoms or carbon atom Number 3-8 cycloalkyl or cycloalkenyl having 3 to 8 carbon atoms ^{of), - SiR 5 R 6 R} 7, -OSiR 5 R 6 R 7 (R 5, R 6, R 7 is C 1 -C -6 linear or branched alkyl, phenyl, and two or all may be the same substituent or all different substituents), haloalkyl, haloalkenyl, haloalkoxy, acylalkoxy, acyloxyalkyl, alkylsulfonylalkyl , Siloxyalkyl, hydroxyalkyl, alkoxyalkyl, haloalkoxyalkyl, alkylthioalkyl, dialkoxyacetal, alkoxyalkoxy, cyanoalkyl, halogen, cyano, nitro, amino, hydroxy, pentahalosulfanyl, benzyl, benzyloxy, phenyl, phenoxy, Pi Substituted with 1 to 4 substituents selected from lysyl, oxazolyl, furyl, thiazolyl, naphthyl, pyrimidinyl, thienyl, benzothiazolyl, benzoxazolyl, benzooxolyl, imide, formyl (—CHO), carboxyl (—COOH) May represent)
B is a) phenyl, benzyl, oxazolyl, isoxazolyl, furyl, benzofuryl, isobenzofuryl, dihydrobenzofuryl, thiazolyl, isothiazolyl, naphthyl, pyrimidinyl, pyrazinyl, quinoxalyl, quinazolyl, pyridyl, quinolyl, isoquinolyl, benzothiazolyl, benzoisothiazolyl Selected from the group consisting of pyrrolyl, indolyl, isoindolyl, benzoxazolyl, benzoisoxazolyl, thienyl, benzothienyl, imidazolyl, benzimidazolyl, pyrazolyl, pyridonyl, triazinyl, triazolyl, thiadiazolyl, oxadiazolyl, tetrazolyl, ferrocenyl A monocyclic or bicyclic ring optionally containing 0 to 3 heteroatoms,
b) linear or branched alkyl having 1 to 6 carbon atoms, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, Linear or branched cycloalkyl having 3 to 8 carbon atoms or cycloalkenyl having 3 to 8 carbon atoms,
c) —SiR ⁵ R ⁶ R ⁷ (R ⁵ , R ⁶ , R ⁷ are linear or branched alkyl or phenyl having 1 to 6 carbon atoms, and even if two or all are the same substituents, all Different substituents may be used),
d) -C (O) OR, -C (O) NHR, -C (O) NR 2, -SO 2 NHR, R in _-SO 2 NR ₂ (where linear 1 to 8 carbon atoms Or branched alkyl, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, cycloalkyl or carbon having 3 to 8 carbon atoms C 3 -C 8 cycloalkenyl, benzyl or cyclic ether), halogen, formyl (—CHO) or carboxyl (—COOH),
e) selected from hydrogen atoms, and in the case of a) and b) B is —C (O) OR, —C (O) R, —R, —OR, —SR, —SO ₂ R, —OC (O) R, —C (O) NHR, —C (O) NR ₂ , —NHSO ₂ R, —NRSO ₂ R, —NHR, —NR ₂ , —NHC (O) R, —NRC (O) R, —NHC _{(O) OR, -NRC (O} ) OR, -N (OR) C (O) OR, -NHSO 2 R, -NRSO 2 R, = NOR, -SO 2 NHR, -SO 2 NR 2 ( here R is linear or branched alkyl having 1 to 8 carbon atoms, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms. Or a cycloalkyl having 3 to 8 carbon atoms, a cycloalkenyl having 3 to 8 carbon atoms, or a cyclic ether), -SiR ⁵ R ⁶ R ⁷ , —OSiR ⁵ R ⁶ R ⁷ (R ⁵ , R ⁶ , R ⁷ are linear or branched alkyl or phenyl having 1 to 6 carbon atoms, and two or all of them are the same substituents. All may be different substituents), haloalkyl, haloalkenyl, haloalkoxy, haloalkylthio, acylalkoxy, acyloxyalkyl, alkylsulfonylalkyl, siloxyalkyl, hydroxyalkyl, alkoxyalkyl, haloalkoxyalkyl, alkylthioalkyl, dialkoxyacetal, Alkoxyalkoxy, cyanoalkyl, halogen, cyano, nitro, amino, hydroxy, pentahalosulfanyl, benzyl, benzyloxy, phenyl, phenoxy, pyridyl, oxazolyl, furyl, thiazolyl, naphthyl, pyrimidinyl, It may be substituted with 1 to 7 substituents selected from thienyl, benzothiazolyl, benzoxazolyl, benzooxolyl, imide, formyl (—CHO), carboxyl (—COOH), and oxo (═O). ]
A sulfonamide compound represented by:   The compound according to claim 1, wherein A is unsubstituted or phenylene having 1 to 4 substituents.   A is a heteroarrangeyl selected from the group consisting of oxazolediyl, isoxazolediyl, frangiyl, thiazolediyl, isothiazolediyl, pyrimidinediyl, pyrazinediyl, pyridinediyl, pyrrolediyl, thiophenediyl, imidazolediyl, pyrazolediyl 6. A compound according to claim 1 wherein heteroarendyl is unsubstituted or has 1 to 7 substituents.   Any one of claims 1-3, wherein B is a monocyclic or bicyclic ring selected from the group consisting of phenyl, furyl, thiazolyl, naphthyl, pyridyl, quinolyl, thienyl, imidazolyl, pyrazolyl, tetrazolyl. The compound according to item 1.   B is linear or branched alkyl having 1 to 6 carbon atoms, linear or branched alkenyl having 2 to 8 carbon atoms, or linear or branched having 3 to 8 carbon atoms. 4. A compound according to any one of claims 1 to 3 which is cycloalkyl. B is —SiR ⁵ R ⁶ R ⁷ (R ⁵ , R ⁶ , R ⁷ are linear or branched alkyl or phenyl having 1 to 6 carbon atoms, and even if two or all of them are the same substituent, The compound according to any one of claims 1 to 3, wherein may be different substituents. B is —C (O) OR, —C (O) NHR, —C (O) NR ₂ , —SO ₂ NHR, —SO ₂ NR ₂ (where R is a straight chain having 1 to 8 carbon atoms) Chain or branched alkyl, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, cycloalkyl having 3 to 8 carbon atoms, or The compound according to any one of claims 1 to 3, which is cycloalkenyl having 3 to 8 carbon atoms, benzyl or cyclic ether), halogen, formyl (-CHO) or carboxyl (-COOH). B is a monocyclic or bicyclic ring selected from the group consisting of phenyl, furyl, thiazolyl, naphthyl, pyridyl, quinolyl, thienyl, imidazolyl, pyrazolyl, tetrazolyl, R ¹ , R ² , R ³ , R ⁴ are each a hydrogen atom, —R, —OR, —SR (where R is a linear or branched alkyl having 1 to 8 carbon atoms, a straight chain having 2 to 8 carbon atoms) Or a branched alkenyl, a linear or branched alkynyl having 2 to 8 carbon atoms, a cycloalkyl having 3 to 8 carbon atoms or a cycloalkenyl having 3 to 8 carbon atoms), haloalkyl, haloalkoxy, The compound according to any one of claims 1 to 3, which is halogen, cyano, nitro, hydroxy, phenyl, phenoxy. B is linear or branched alkyl having 1 to 6 carbon atoms, linear or branched alkenyl having 2 to 8 carbon atoms, or linear or branched having 3 to 8 carbon atoms. Cycloalkyl, R ¹ , R ² , R ³ , R ⁴ are each a hydrogen atom, —R, —OR, —SR (where R is a linear or branched group having 1 to 8 carbon atoms) Alkyl, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, cycloalkyl having 3 to 8 carbon atoms, or 3 to 3 carbon atoms The compound of any one of claims 1 to 3, which is haloalkyl, haloalkoxy, halogen, cyano, nitro, hydroxy, phenyl, or phenoxy. B is —SiR ⁵ R ⁶ R ⁷ (R ⁵ , R ⁶ , R ⁷ are linear or branched alkyl or phenyl having 1 to 6 carbon atoms, and even if two or all of them are the same substituent, And R ¹ , R ² , R ³ , and R ⁴ are each a hydrogen atom, —R, —OR, —SR (where R is a straight chain having 1 to 8 carbon atoms). Chain or branched alkyl, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, or cycloalkyl having 3 to 8 carbon atoms, or The compound according to any one of claims 1 to 3, which is cycloalkenyl having 3 to 8 carbon atoms), haloalkyl, haloalkoxy, halogen, cyano, nitro, hydroxy, phenyl, or phenoxy. B is —C (O) OR, —C (O) NHR, —C (O) NR ₂ , —SO ₂ NHR, —SO ₂ NR ₂ (where R is a straight chain having 1 to 8 carbon atoms) Chain or branched alkyl, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, cycloalkyl having 3 to 8 carbon atoms, or A cycloalkenyl, benzyl or cyclic ether having 3 to 8 carbon atoms), halogen, formyl (—CHO) or carboxyl (—COOH), and each of R ¹ , R ² , R ³ and R ⁴ is a hydrogen atom. , -R, -OR, -SR (where R is linear or branched alkyl having 1 to 8 carbon atoms, linear or branched alkenyl having 2 to 8 carbon atoms, carbon atom) 2-8 linear or branched alkynyl or 3 carbon atoms A cycloalkyl or a cycloalkyl having 3 to 8 carbon atoms), haloalkyl, haloalkoxy, halogen, cyano, nitro, hydroxy, phenyl, or phenoxy. The described compound. B is a monocyclic or bicyclic ring selected from the group consisting of phenyl, furyl, thiazolyl, naphthyl, pyridyl, quinolyl, thienyl, imidazolyl, pyrazolyl, tetrazolyl, and R ¹ is bonded to R ^2. The compound according to any one of claims 1 to 3, which is a benzene ring formed together with a carbon atom on the pyridine ring. B is linear or branched alkyl having 1 to 6 carbon atoms, linear or branched alkenyl having 2 to 8 carbon atoms, or linear or branched having 3 to 8 carbon atoms. The compound according to any one of claims 1 to 3, which is cycloalkyl and is a benzene ring which R ¹ is bonded to R ² to form together with the carbon atom on the pyridine ring. B is —SiR ⁵ R ⁶ R ⁷ (R ⁵ , R ⁶ , R ⁷ are linear or branched alkyl or phenyl having 1 to 6 carbon atoms, and even if two or all of them are the same substituent, is also be) with different substituents, R ¹ is a benzene ring to form together with the carbon atoms on the pyridine ring bonded to R ^2, a compound according to any one of claims 1 to 3. B is —C (O) OR, —C (O) NHR, —C (O) NR ₂ , —SO ₂ NHR, —SO ₂ NR ₂ (where R is a straight chain having 1 to 8 carbon atoms) Chain or branched alkyl, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, cycloalkyl having 3 to 8 carbon atoms, or A cycloalkenyl, benzyl or cyclic ether having 3 to 8 carbon atoms), halogen, formyl (—CHO) or carboxyl (—COOH), and R ¹ is bonded to R ² together with the carbon atom on the pyridine ring. The compound according to any one of claims 1 to 3, which is a benzene ring to be formed. The sulfonic acid derivative represented by the formula [II] and the amine derivative represented by the formula [III] are reacted in the presence of a base and a solvent. A method for producing a sulfonamide derivative.

(In the formula, R ¹ , R ² , R ³ , R ⁴ , A and B have the meanings described in claim 1). The method for producing a sulfonamide derivative represented by the formula [I] according to claim 1, wherein a substituent is introduced into the terminal alkyne represented by the formula [I-1] using a coupling reaction.

(Wherein X is bromine or iodine, B is phenyl, heteroaryl, alkenyl, R ¹ , R ² , R ³ , R ⁴ and A have the meanings given in claim 1) The sulfonamide derivative represented by the formula [I] according to claim 1, wherein a substituent is introduced from the compound represented by the formula [I-2] and the terminal alkyne [V] using a coupling reaction. Manufacturing method.

(In the formula, X is bromine or iodine, R ¹ , R ² , R ³ , R ⁴ , A and B have the meanings described in claim 1). A pest control agent comprising one or more sulfonamide derivatives represented by the formula [I] according to claim 1 as an active ingredient.