JP2017075161A - Pest control composition and use therefor - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a pest control composition having excellent pest control effect.SOLUTION: A pest control composition comprises a compound represented by formula (1) or an N oxide compound thereof, and at least one compound selected from group (a) an insecticide such as cypermethrin and imidacloprid or group (b) a bactericide such as azaconazole and boscalid, where A is N or a CR; R1 is alkyl, alkenyl or the like; R2 and R3 independently represent H, C1-C6 alkyl substituted/unsubstituted with a halogen atom, C2-C6 alkoxycarbonyl, cyano or a halogen atom; Ris halogen and alkyl; Ris halogen and alkyl, phenyl or the like; Ris H or halogen.SELECTED DRAWING: None

Description

  The present invention relates to a pest control composition and use thereof.

  Conventionally, many compounds are known as an active ingredient of a pest control composition (for example, refer nonpatent literature 1).

MeisterPro Crop Protection Handbook Vol. 100 (2014), published by Meister Media World, ISBN 1-892829-27-4.

  This invention makes it a subject to provide the pest control composition which has the outstanding control effect with respect to a pest.

  As a result of studying to find a pest control composition having an excellent control effect against pests, the present inventor has found that the compound represented by the formula (1) and one selected from the group (a) or the group (b) It has been found that a composition containing the above compounds has an excellent control effect against pests.

［式中、
Ａは、窒素原子、又はＣＲ⁶を表し、
Ｒ¹は、Ｃ２−Ｃ１０アルキル基、Ｃ３−Ｃ１０アルケニル基、Ｃ３−Ｃ１０アルキニル基、（Ｃ１−Ｃ５アルキル）−Ｏ−（Ｃ２−Ｃ５アルキル）基、（Ｃ３−Ｃ５アルケニル）−Ｏ−（Ｃ２−Ｃ５アルキル）基、（Ｃ３−Ｃ５アルキニル）−Ｏ−（Ｃ２−Ｃ５アルキル）基、（Ｃ１−Ｃ５アルキル）−Ｓ（Ｏ）_m−（Ｃ２−Ｃ５アルキル）基、（Ｃ３−Ｃ５アルケニル）−Ｓ（Ｏ）_m−（Ｃ２−Ｃ５アルキル）基、（Ｃ３−Ｃ５アルキニル）−Ｓ（Ｏ）_m−（Ｃ２−Ｃ５アルキル）基、又は（Ｃ１−Ｃ５アルキル）−Ｃ（Ｏ）−（Ｃ１−Ｃ５アルキル）基を表し（但し、Ｒ¹は１以上のハロゲン原子を有する）、
Ｒ²およびＲ³は、それぞれ独立して水素原子、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルキル基、Ｃ２−Ｃ６アルコキシカルボニル基、シアノ基、又はハロゲン原子を表し、
Ｒ⁴は、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６鎖式炭化水素基表し、
Ｒ⁵は、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６鎖式炭化水素基、群Ａより選ばれる１以上の原子もしくは基を有していてもよいフェニル基、群Ｂより選ばれるいずれかの５員芳香族複素環基（該５員芳香族複素環基は、群Ａより選ばれる１以上の原子又は基を有していてもよい。）、群Ｃより選ばれるいずれかの６員芳香族複素環基（該６員芳香族複素環基は、群Ａより選ばれる１以上の原子又は基を有していてもよい。）、群Ｄより選ばれるいずれかの３−７員非芳香族複素環基（該３−７員非芳香族複素環基は、ハロゲン原子及びＣ１−Ｃ６アルキル基からなる群より選ばれる１以上の原子又は基を有していてもよい。）、ＯＲ⁷、ＮＲ⁸Ｒ⁹、ＮＲ⁸Ｃ（Ｏ）Ｒ¹⁰、ＮＲ⁸Ｃ（Ｏ）ＯＲ¹¹、ＮＲ⁸Ｃ（Ｏ）ＮＲ¹²Ｒ¹³、Ｎ＝ＣＨＮＲ¹²Ｒ¹³、Ｎ＝Ｓ（Ｏ）_xＲ¹²Ｒ¹³、Ｓ（Ｏ）_yＲ¹²、Ｃ（Ｏ）ＯＲ⁸、シアノ基、又はハロゲン原子を表し、
Ｒ⁶は、水素原子、又はハロゲン原子を表し、
Ｒ⁷は、水素原子、Ｃ１−Ｃ６アルキル基、Ｃ３−Ｃ６アルケニル基、Ｃ３−Ｃ６アルキニル基、（Ｃ１−Ｃ３アルキル）−Ｏ−（Ｃ１−Ｃ３アルキル）基、（Ｃ１−Ｃ３アルキル）−Ｓ（Ｏ）_y−（Ｃ１−Ｃ３アルキル）基、Ｃ３−Ｃ７シクロアルキル基、（Ｃ３−Ｃ７シクロアルキル）−（Ｃ１−Ｃ３アルキル）基（但し、該Ｃ１−Ｃ６アルキル基、Ｃ３−Ｃ６アルケニル基、Ｃ３−Ｃ６アルキニル基、（Ｃ１−Ｃ３アルキル）−Ｏ−（Ｃ１−Ｃ３アルキル）基、（Ｃ１−Ｃ３アルキル）−Ｓ（Ｏ）_y−（Ｃ１−Ｃ３アルキル）基、Ｃ３−Ｃ７シクロアルキル基、及び（Ｃ３−Ｃ７シクロアルキル）−（Ｃ１−Ｃ３アルキル）基は、１以上のハロゲン原子を有していてもよい）、又はフェニルＣ１−Ｃ３アルキル基（該フェニルＣ１−Ｃ３アルキル基のフェニル部分は群Ａより選ばれる１以上の原子又は基を有していてもよい。）を表し、
Ｒ⁸は、水素原子、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルキル基、１以上のハロゲン原子を有していてもよいＣ３−Ｃ６アルケニル基、又は１以上のハロゲン原子を有していてもよいＣ３−Ｃ６アルキニル基を表し、
Ｒ⁹は、水素原子、Ｃ１−Ｃ６アルキル基、Ｃ３−Ｃ６アルケニル基、Ｃ３−Ｃ６アルキニル基、（Ｃ１−Ｃ３アルキル）−Ｏ−（Ｃ１−Ｃ３アルキル）基、（Ｃ１−Ｃ３アルキル）−Ｓ（Ｏ）_y−（Ｃ１−Ｃ３アルキル）基、Ｃ３−Ｃ７シクロアルキル基、（Ｃ３−Ｃ７シクロアルキル）−（Ｃ１−Ｃ３アルキル）基（但し、該Ｃ１−Ｃ６アルキル基、Ｃ３−Ｃ６アルケニル基、Ｃ３−Ｃ６アルキニル基、（Ｃ１−Ｃ３アルキル）−Ｏ−（Ｃ１−Ｃ３アルキル）基、（Ｃ１−Ｃ３アルキル）−Ｓ（Ｏ）_y−（Ｃ１−Ｃ３アルキル）基、Ｃ３−Ｃ７シクロアルキル基、及び（Ｃ３−Ｃ７シクロアルキル）−（Ｃ１−Ｃ３アルキル）基は、１以上のハロゲン原子を有していてもよい）、シアノＣ１−Ｃ６アルキル基、フェニルＣ１−Ｃ３アルキル基（該フェニルＣ１−Ｃ３アルキル基のフェニル部分は群Ａより選ばれる１以上の原子又は基を有していてもよい。）、又は（５もしくは６員ヘテロアリール）Ｃ１−Ｃ３アルキル基（該（５もしくは６員ヘテロアリール）Ｃ１−Ｃ３アルキル基の５もしくは６員ヘテロアリール部分は群Ａより選ばれる１以上の原子もしくは基を有していてもよい。）を表し、
Ｒ¹⁰は、水素原子、Ｃ１−Ｃ６アルキル基、Ｃ３−Ｃ６アルケニル基、Ｃ３−Ｃ６アルキニル基、Ｃ３−Ｃ７シクロアルキル基、（Ｃ３−Ｃ７シクロアルキル）−（Ｃ１−Ｃ３アルキル）基（但し、該Ｃ１−Ｃ６アルキル基、Ｃ３−Ｃ６アルケニル基、Ｃ３−Ｃ６アルキニル基、Ｃ３−Ｃ７シクロアルキル基、及び（Ｃ３−Ｃ７シクロアルキル）−（Ｃ１−Ｃ３アルキル）基は、１以上のハロゲン原子を有していてもよい）、又はフェニルＣ１−Ｃ３アルキル基（該フェニルＣ１−Ｃ３アルキル基のフェニル部分は群Ａより選ばれる１以上の原子又は基を有していてもよい。）を表し、
Ｒ¹¹は、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルキル基、１以上のハロゲン原子を有していてもよいＣ３−Ｃ６アルケニル基、１以上のハロゲン原子を有していてもよいＣ３−Ｃ６アルキニル基、１以上のハロゲン原子を有していてもよいＣ３−Ｃ７シクロアルキル基、（Ｃ３−Ｃ７シクロアルキル）−（Ｃ１−Ｃ３アルキル）基（但し、該（Ｃ３−Ｃ７シクロアルキル）−（Ｃ１−Ｃ３アルキル）基は１以上のハロゲン原子を有していてもよい）、又はフェニルＣ１−Ｃ３アルキル基（該フェニルＣ１−Ｃ３アルキル基のフェニル部分は群Ａより選ばれる１以上の原子又は基を有していてもよい。）を表し、
Ｒ¹²及びＲ¹³は、それぞれ独立して、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルキル基を表し、
Ｒ¹⁴は、水素原子、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルキル基、１以上のハロゲン原子を有していてもよいＣ２−Ｃ６アルキルカルボニル基、又は１以上のハロゲン原子を有していてもよいＣ２−Ｃ６アルコキシカルボニル基を表し、
ｎは、０、１、又は２を表し、
ｍは、０、１、又は２を表し、
ｐは、０、１、２又は３を表し（ここで、ｐが２又は３を表す場合に、複数のＲ⁵は各々同一でも異なっていてもよい）、
ｘは、０、又は１を表し、
ｙは、０、１、又は２を表す。
群Ａ：１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルキル基、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルコキシ基、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルキルスルファニル基、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルキルスルフィニル基、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルキルスルホニル基、シアノ基、及びハロゲン原子からなる群。
群Ｂ：

群Ｃ：

群Ｄ：

］で示される化合物、又はそのＮオキシド化合物（以下、式（１）で示されるピリダジン化合物及びそのＮオキシド化合物を本ピリダジン化合物と記す）と、
下記群（ａ）又は下記群（ｂ）より選ばれる１種以上の化合物（以下、本化合物と記す）と
を含有する有害生物防除組成物（以下、本発明組成物と記す）。
群（ａ）：
下記亜群ａ−１、ａ−２、ａ−３、ａ−４、ａ−５、ａ−６及びａ−７からなる群。
亜群ａ−１：
アセタミプリド（acetamiprid）、クロチアニジン（clothianidin）、ジノテフラン（dinotefuran）、イミダクロプリド（imidacloprid）、ニテンピラム（nitenpyram）、チアクロプリド（thiacloprid）、チアメトキサム（thiamethoxam）、フルピラジフロン（flupyradifurone）、スルホキサフロル（sulfoxaflor）、トリフルメゾピリム（triflumezopyrim）、ジクロロメソチアズ（dicloromezotiaz）及び下記式で示される化合物(CAS登録番号1689566-03-7、以下「殺虫化合物α」と記すことがある)

からなる、ニコチン性アセチルコリン受容体競合的モジュレーターの群。
亜群ａ−２：
アクリナトリン（acrinathrin）、アレスリン（allethrin）、ビフェントリン（bifenthrin）、カッパビフェントリン（kappa-bifenthrin）、ビオアレスリン（bioallethrin）、ビオレスメトリン（bioresmethrin）、シクロプロトリン（cycloprothrin）、シフルトリン（cyfluthrin）、ベータ−シフルトリン（beta-cyfluthrin）、シハロトリン（cyhalothrin）、ガンマシハロトリン（gamma-cyhalothrin）、ラムダシハロトリン（lambda-cyhalothrin）、シペルメトリン（cypermethrin）、アルファシペルメトリン（alpha-cypermethrin）、べータシペルメトリン（beta-cypermethrin）、シータシペルメトリン（theta-cypermethrin）、ゼータシペルメトリン（zeta-cypermethrin）、シグマシペルメトリン（sigma-cypermethrin）、シフェノトリン（cyphenothrin）、デルタメトリン（deltamethrin）、エンペントリン（empenthrin）、エスフェンバレレート（esfenvalerate）、エトフェンプロックス（etofenprox）、フェンプロパトリン（fenpropathrin）、フェンバレレート（fenvalerate）、フルシトリネート（flucythrinate）、フルメトリン（flumethrin）、フルバリネート（fluvalinate）、タウフルバリネート（tau-fluvalinate）、ハルフェンプロックス（halfenprox）、ヘプタフルトリン（heptafluthrin）、イミプロトリン（imiprothrin）、カデスリン（kadethrin）、メペルフルトリン（meperfluthrin）、モンフルオロトリン（momfluorothrin）、ペルメトリン（permethrin）、フェノトリン（phenothrin）、プラレトリン（prallethrin）、ピレトリン（pyrethrins）、レスメトリン（resmethrin）、シラフルオフェン（silafluofen）、テフルトリン（tefluthrin）、カッパテフルトリン（kappa-tefluthrin）、テトラメトリン（tetramethrin）、テトラメチルフルトリン（tetramethylfluthrin）、トラロメトリン（tralomethrin）、トランスフルトリン（transfluthrin）、ベンフルトリン（benfluthrin）、フルフェンプロックス（flufenoprox）、フルメスリン（flumethrin）、フラメトリン（furamethrin）、メトフルトリン（metofluthrin）、プロフルトリン（profluthrin）及びジメフルトリン（dimefluthrin）からなる、ナトリウムチャネルモジュレーターの群。
亜群ａ−３：
エチプロール（ethiprole）、フィプロニル（fipronil）及びフルフィプロール（flufiprole）からなるGABA作動性塩素イオンチャネルブロッカー、並びに、アフォクソラネル（afoxalaner）、フルララネル（fluralaner）、ブロフラニリド（broflanilide）及びフルキサメタミド（fluxametamide）からなるGABA作動性塩素イオンチャネルアロステリックモジュレーターの群。
亜群ａ−４：
クロラントラニリプロール（chlorantraniliprole）、シアントラニルプロール（cyantraniliprole）、シクラニリプロール（cycloniliprole）、フルベンジアミド（flubendiamide）、テトラニリプロール（tetraniliprole）及びシハロジアミド（cyhalodiamide）からなる、リアノジン受容体モジュレーターの群。
亜群ａ−５：
アラニカルブ（alanycarb）、アルジカルブ（aldicarb）、ベンダイオカルブ（bendiocarb）、ベンフラカルブ（benfuracarb）、ブトカルボキシム（butocarboxim）、ブトキシカルボキシム（butoxycarboxim）、カルバリル（carbaryl：NAC）、カルボフラン（carbofuran）、カルボスルファン（carbosulfan）、エチオフェンカルブ（ethiofencarb）、フェノブカルブ（fenobucarb：BPMC）、ホルメタネート（formetanate）、フラチオカルブ（furathiocarb）、イソプロカルブ（isoprocarb：MIPC）、メチオカルブ（methiocarb）、メソミル（methomyl）、メトルカルブ（metolcarb：MTMC）、オキサミル（oxamyl）、ピリミカーブ（pirimicarb）、プロポキスル（propoxur：PHC）、チオジカルブ（thiodicarb）、チオファノックス（thiofanox）、トリアザメート（triazamate）、トリメタカルブ（trimethacarb）、XMC及びキシリルカルブ（xylylcarb：MPMC）からなる、カーバメート系のアセチルコリンエステラーゼ（AChE）阻害剤の群。
亜群ａ−６：
アバメクチン（abamectin）、フルエンスルホン（fluensulfone）、チオキサザフェン（tioxazafen）、及びフルアザインドリジン（fluazaindolizine）からなる、殺線虫活性化合物の群。
亜群ａ−７：
菌根菌（Mycorrhiza Fungi）、アルスロボトリス・ダクチロイデス（Arthrobotrys dactyloides）、バチルス・チューリンゲンシス（Bacillus thuringiensis）、バチルス・フィルムス（Bacillus firmus）、バチルス・メガテリウム（Bacillus megaterium）、バチルス・アミロリケファシエンス（Bacillus amyloliquefaciens）、ヒルステラ・ロッシリエンシス（Hirsutella rhossiliensis）、ヒルステラ・ミネソテンシス（Hirsutella minnesotensis）、モナクロスポリウム・フィマトパガム（Monacrosporium phymatopagus）、パスツーリア・ニシザワエ（Pasteuria nishizawae）、パスツーリア・ペネトランス（Pasteuria penetrans）、パスツーリア・ウスガエ（Pasteuria usgae）、バーティシリウム・クラミドスポリウム（Verticillium chlamydosporium）及びハーピンタンパク（Harpin protein）からなる、微生物資材の群。
群（ｂ）：
下記亜群ｂ−１、ｂ−２、ｂ−３、ｂ−４、ｂ−５、ｂ−６、ｂ−７、ｂ−８及びｂ−９からなる群。
亜群ｂ−１：
アザコナゾール（azaconazole）、ビテルタノール（bitertanol）、ブロムコナゾール（bromuconazole）、シプロコナゾール（cyproconazole）、ジフェノコナゾール（difenoconazole）、ジニコナゾール（diniconazole）、ジニコナゾールM（diniconazole−M）、エポキシコナゾール（epoxiconazole）、エタコナゾール（etaconazole）、フェナリモル（fenarimol）、フェンブコナゾール（fenbuconazole）、フルキンコナゾール（fluquinconazole）、キンコナゾール(quinconazole）、フルシラゾール（flusilazole）、フルトリアホール（flutriafol）、ヘキサコナゾール（hexaconazole）、イマザリル（imazalil）、イミベンコナゾール（imibenconazole）、イプコナゾール（ipconazole）、メトコナゾール（metconazole）、ミクロブタニル（myclobutanil）、ヌアリモール（nuarimol）、オキスポコナゾール（oxpoconazole）、オキスポコナゾールフマル酸塩（oxpoconazole fumarate）、ペフラゾエート（pefurazoate）、ペンコナゾール（penconazole）、プロクロラズ（prochloraz）、プロピコナゾール（propiconazole）、プロチオコナゾール（prothioconazole）、ピリフェノックス（pyrifenox）、ピリソキサゾール（pyrisoxazole）、シメコナゾール（simeconazole）、テブコナゾール（tebuconazole）、テトラコナゾール（tetraconazole）、トリアジメホン（triadimefon）、トリアジメノール（triadimenol）、トリフルミゾール（triflumizole）、トリホリン（triforine）及びトリチコナゾール（triticonazole）からなる、ステロール生合成阻害剤の群。
亜群ｂ−２：
アゾキシストロビン（azoxystrobin）、クモキシストロビン（coumoxystrobin）、ジモキシストロビン（dimoxystrobin）、エノキサストロビン（enoxastrobin）、ファモキサドン（famoxadone）、フェンアミドン（fenamidone）、フェナミンストロビン（fenaminstrobin）、フルフェノキシストロビン（flufenoxystrobin）、フルオキサストロビン（fluoxastrobin）、クレソキシム−メチル（kresoxim-methyl）、マンデストロビン（mandestrobin）、メトミノストロビン（metominostrobin）、オリサストロビン（orysastrobin）、ピコキシストロビン（picoxystrobin）、ピラクロストロビン（pyraclostrobin）、ピラメトストロビン（pyrametostrobin）、ピラオキシストロビン（pyraoxystrobin）、トリフロキシストロビン(trifloxystrobin)、ピリベンカルブ（pyribencarb）、トリクロピリカルブ（triclopyricarb）、シアゾファミド（cyazofamid）及びアミスルブロム（amisulbrom）からなる、Qo阻害剤（Quinone outside inhibitors）の群。
亜群ｂ−３：
ベナラキシル（benalaxyl）、ベナラキシルM（benalaxyl-M）、フララキシル（furalaxyl）、メタラキシル（metalaxyl）、メタラキシルM（metalaxyl-M）、オキサジキシル（oxadixyl）及びオフラセ（ofurace）からなる、ＲＮＡポリメラーゼＩ阻害剤の群。
亜群ｂ−４：
ベノダニル（benodanil）、ベンゾビンジフルピル（benzovindiflupyr）、ビキサフェン（bixafen）、ボスカリド（boscalid）、カルボキシン（carboxin）、フェンフラム（fenfuram）、フルオピラム（fluopyram）、フルトラニル（flutolanil）、フルキサピロキサド（fluxapyroxad）、フラメトピル（furametpyr）、イソフェタミド（isofetamid）、イソピラザム（isopyrazam）、メプロニル（mepronil）、オキシカルボキシン（oxycarboxin）、ペンチオピラド（penthiopyrad）、ペンフルフェン（penflufen）、セダキサン（sedaxane）、チフルザミド（thifluzamide）、ピラジフルミド（pyraziflumid）、ピジフルメトフェン(pydiflumetofen、ＣＡＳ登録番号1228284-64-7)、３−ジフルオロメチル−１−メチル−Ｎ−（１，１，３−トリメチルインダン−４−イル）ピラゾール−４−カルボキサミド（ＣＡＳ登録番号141573-94-6、以下「殺菌化合物β１」と記すことがある）、３−ジフルオロメチル−１−メチル−Ｎ−［（３Ｒ）−１，１，３−トリメチルインダン−４−イル］ピラゾール−４−カルボキサミド（ＣＡＳ登録番号1352994-67-2、以下「殺菌化合物β２」と記すことがある）、３−ジフルオロメチル−Ｎ−（７−フルオロ−１，１，３−トリメチルインダン−４−イル）−１−メチルピラゾール−４−カルボキサミド（ＣＡＳ登録番号1383809-87-7、以下「殺菌化合物β３」と記すことがある）、３−ジフルオロメチル−Ｎ−［（３Ｒ）−７−フルオロ−１，１，３−トリメチルインダン−４−イル］−１−メチルピラゾール−４−カルボキサミド（ＣＡＳ登録番号1513466-73-3、以下「殺菌化合物β４」と記すことがある）及びＮ−シクロプロピル−３−（ジフルオロメチル）−５−フルオロ−Ｎ−（５−クロロ−２−イソプロピルベンジル）−１−メチル−１Ｈ−ピラゾール−４−カルボキサミド（ＣＡＳ登録番号1255734-28-1、以下「殺菌化合物β５」と記すことがある）からなる、コハク酸脱水素酵素阻害剤の群。
亜群ｂ−５：
ベノミル（benomyl）、カルベンダジム（carbendazim）、フベリダゾール（fuberidazole）、チアベンダゾール（thiabendazole）、チオファネート（thiophanate）、チオファネートメチル（thiophanate-methyl）、ジエトフェンカルブ（diethofencarb）、ゾキサミド（zoxamide）及びエタボキサム(ethaboxam)からなる、βチューブリン重合阻害剤の群。
亜群ｂ−６：
フェルバム（ferbam）、マンゼブ（mancozeb）、マンネブ（maneb）、メチラム（metiram）、プロピネブ（propineb）、チウラム（thiram）、ジネブ（zineb）、ジラム（ziram）、キャプタン（captan）、キャプタホール（captafol）、ホルペット（folpet）、クロロタロニル（chlorothalonil）、トリルフルアニド（tolylfluanid）、グアザチン（guazatine）、イミノクタジン（iminoctadine）、アニラジン（anilazine）、ジチアノン（dithianon）、キノメチオナート（chinomethionat or quinomethionate）及びフルオルイミド（fluoroimide）からなる、多作用点接触活性化合物の群。
亜群ｂ−７：
ジメトモルフ（dimethomorph）、フルモルフ（flumorph）、ピリモルフ（pyrimorph）、ベンチアバリカルブ（benthiavalicarb）、ベンチアバリカルブイソプロピル（benthivalicarb-isopropyl）、イプロバリカルブ（iprovalicarb）、バリフェナレート（valifenalate）及びマンジプロパミド（mandipropamid）からなる、セルロース合成阻害剤の群。
亜群ｂ−８：
フェンピクロニル（fenpiclonil）、フルジオキソニル(fludioxonil)、クロゾリネート（chlozolinate）、イプロジオン（iprodione）、プロシミドン（procymidone）及びビンクロゾリン（vinclozolin）からなる、浸透圧シグナル伝達におけるMAP（mitogen-activated protein）/ヒスチジンキナーゼ阻害剤の群。
亜群ｂ−９：
トルクロホスメチル(tolclofos-methyl)、オキサチアピプロリン(oxathiapiprolin)、ピカルブトラゾクス(picarbutrazox)、フルオピコリド（fluopicolide）及びシルチオファム(silthiofam)からなる、その他の殺菌剤の群。
［２］
式（１）で示される化合物と、群（ａ）より選ばれる１種以上の化合物との含有量の比が、重量比で１００：１〜１：１００である［１］に記載の有害生物防除組成物。
［３］
式（１）で示される化合物と、群（ａ）より選ばれる１種以上の化合物との含有量の比が、重量比で１０：１〜１：１０である［１］に記載の有害生物防除組成物。
［４］
式（１）で示される化合物と、群（ｂ）より選ばれる１種以上の化合物との含有量の比が、重量比で１００００：１〜１：１００である［１］に記載の有害生物防除組成物。
［５］
式（１）で示される化合物と、群（ｂ）より選ばれる１種以上の化合物との含有量の比が、重量比で１０００：１〜１：１０である［１］に記載の有害生物防除組成物。
［６］
［１]〜［５］のいずれかに記載の有害生物防除組成物の有効量を、有害生物又は有害生物の生息場所に施用する工程を有する有害生物の防除方法。
［７］
［１]〜［５］のいずれかに記載の有害生物防除組成物の有効量を、植物、植物種子、球根又は植物を栽培する土壌に施用する工程を有する有害生物の防除方法。
［８］
［１]〜［５］のいずれかに記載の有害生物防除組成物の有効量を付着させた植物種子又は球根。 The present invention is as follows.
[1]
Formula (1):

[Where:
A represents a nitrogen atom or CR ⁶ ;
R ¹ is a C2-C10 alkyl group, a C3-C10 alkenyl group, a C3-C10 alkynyl group, a (C1-C5 alkyl) -O- (C2-C5 alkyl) group, a (C3-C5 alkenyl) -O- (C2 -C5 alkyl) group, (C3-C5 alkynyl) -O- (C2-C5 alkyl) group, (C1-C5 alkyl) -S (O) _m- (C2-C5 alkyl) group, (C3-C5 alkenyl) -S (O) _m- (C2-C5 alkyl) group, (C3-C5 alkynyl) -S (O) _m- (C2-C5 alkyl) group, or (C1-C5 alkyl) -C (O)-( C1-C5 alkyl) group (wherein R ¹ has one or more halogen atoms),
R ² and R ³ each independently represent a hydrogen atom, a C1-C6 alkyl group optionally having one or more halogen atoms, a C2-C6 alkoxycarbonyl group, a cyano group, or a halogen atom,
R ⁴ represents a C1-C6 chain hydrocarbon group which may have one or more halogen atoms,
R ⁵ is a C1-C6 chain hydrocarbon group which may have one or more halogen atoms, a phenyl group which may have one or more atoms or groups selected from Group A, and a group B. Any of the five-membered aromatic heterocyclic groups selected from the group C (the five-membered aromatic heterocyclic group may have one or more atoms or groups selected from the group A). 6-membered aromatic heterocyclic group (the 6-membered aromatic heterocyclic group may have one or more atoms or groups selected from group A), and any 3- 7-membered non-aromatic heterocyclic group (The 3-7-membered non-aromatic heterocyclic group may have one or more atoms or groups selected from the group consisting of halogen atoms and C1-C6 alkyl groups. ^{), OR 7, NR 8 R} 9, NR 8 C (O) R 10, NR 8 C (O) OR 11, NR 8 C (O) NR 12 R 13 ^{N = CHNR 12 R 13, N} = S (O) x R 12 R 13, S (O) y R 12, C (O) OR 8, cyano group, or a halogen atom,
R ⁶ represents a hydrogen atom or a halogen atom,
R ⁷ represents a hydrogen atom, a C1-C6 alkyl group, a C3-C6 alkenyl group, a C3-C6 alkynyl group, a (C1-C3 alkyl) -O- (C1-C3 alkyl) group, or a (C1-C3 alkyl) -S. (O) _y- (C1-C3 alkyl) group, C3-C7 cycloalkyl group, (C3-C7 cycloalkyl)-(C1-C3 alkyl) group (provided that the C1-C6 alkyl group, C3-C6 alkenyl group) , C3-C6 alkynyl group, (C1-C3 alkyl) -O- (C1-C3 alkyl) group, (C1-C3 alkyl) -S (O) _y- (C1-C3 alkyl) group, C3-C7 cycloalkyl Group, and (C3-C7 cycloalkyl)-(C1-C3 alkyl) group may have one or more halogen atoms), or phenyl C1-C3 alkyl group (the phenyl C1-C Phenyl moiety of the alkyl group may have one or more atoms or groups selected from the group A.) Represent,
R ⁸ represents a hydrogen atom, a C1-C6 alkyl group optionally having one or more halogen atoms, a C3-C6 alkenyl group optionally having one or more halogen atoms, or one or more halogen atoms. Represents a C3-C6 alkynyl group which may have,
R ⁹ represents a hydrogen atom, a C1-C6 alkyl group, a C3-C6 alkenyl group, a C3-C6 alkynyl group, a (C1-C3 alkyl) -O- (C1-C3 alkyl) group, or a (C1-C3 alkyl) -S. (O) _y- (C1-C3 alkyl) group, C3-C7 cycloalkyl group, (C3-C7 cycloalkyl)-(C1-C3 alkyl) group (provided that the C1-C6 alkyl group, C3-C6 alkenyl group) , C3-C6 alkynyl group, (C1-C3 alkyl) -O- (C1-C3 alkyl) group, (C1-C3 alkyl) -S (O) _y- (C1-C3 alkyl) group, C3-C7 cycloalkyl Group, and (C3-C7 cycloalkyl)-(C1-C3 alkyl) group may have one or more halogen atoms), cyano C1-C6 alkyl group, phenyl C1-C3 alkyl group. A group (the phenyl portion of the phenyl C1-C3 alkyl group may have one or more atoms or groups selected from group A), or a (5- or 6-membered heteroaryl) C1-C3 alkyl group (the (5- or 6-membered heteroaryl) the 5- or 6-membered heteroaryl part of the C1-C3 alkyl group may have one or more atoms or groups selected from group A),
R ¹⁰ represents a hydrogen atom, a C1-C6 alkyl group, a C3-C6 alkenyl group, a C3-C6 alkynyl group, a C3-C7 cycloalkyl group, a (C3-C7 cycloalkyl)-(C1-C3 alkyl) group (provided that The C1-C6 alkyl group, C3-C6 alkenyl group, C3-C6 alkynyl group, C3-C7 cycloalkyl group, and (C3-C7 cycloalkyl)-(C1-C3 alkyl) group have one or more halogen atoms. Or a phenyl C1-C3 alkyl group (the phenyl portion of the phenyl C1-C3 alkyl group may have one or more atoms or groups selected from group A);
R ¹¹ has a C1-C6 alkyl group optionally having one or more halogen atoms, a C3-C6 alkenyl group optionally having one or more halogen atoms, and one or more halogen atoms. Or a C3-C6 alkynyl group, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, a (C3-C7 cycloalkyl)-(C1-C3 alkyl) group (provided that the (C3-C7 The cycloalkyl)-(C1-C3 alkyl) group may have one or more halogen atoms), or a phenyl C1-C3 alkyl group (the phenyl portion of the phenyl C1-C3 alkyl group is selected from group A) Which may have one or more atoms or groups,
R ¹² and R ¹³ each independently represent a C1-C6 alkyl group optionally having one or more halogen atoms,
R ¹⁴ is a hydrogen atom, a C1-C6 alkyl group optionally having one or more halogen atoms, a C2-C6 alkylcarbonyl group optionally having one or more halogen atoms, or one or more halogen atoms. Represents a C2-C6 alkoxycarbonyl group optionally having
n represents 0, 1, or 2;
m represents 0, 1, or 2;
p represents 0, 1, 2 or 3 (wherein, when p represents 2 or 3, a plurality of R ⁵ may be the same or different from each other);
x represents 0 or 1,
y represents 0, 1, or 2.
Group A: a C1-C6 alkyl group that may have one or more halogen atoms, a C1-C6 alkoxy group that may have one or more halogen atoms, or one or more halogen atoms A good C1-C6 alkylsulfanyl group, a C1-C6 alkylsulfinyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally having one or more halogen atoms, a cyano group, and A group consisting of halogen atoms.
Group B:

Group C:

Group D:

Or an N oxide compound thereof (hereinafter, the pyridazine compound represented by the formula (1) and the N oxide compound thereof will be referred to as the present pyridazine compound),
A pest control composition (hereinafter referred to as the present invention composition) containing one or more compounds selected from the following group (a) or the following group (b) (hereinafter referred to as the present compound).
Group (a):
The group consisting of the following subgroups a-1, a-2, a-3, a-4, a-5, a-6 and a-7.
Subgroup a-1:
Acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, flupyrifurone, flupyradifurone ), Dichloromesothiaz (dicloromezotiaz) and a compound represented by the following formula (CAS registration number 1689566-03-7, hereinafter sometimes referred to as “insecticidal compound α”)

A group of competitive modulators of nicotinic acetylcholine receptors.
Subgroup a-2:
Acrinathrin, allethrin, bifenthrin, kappa-bifenthrin, bioallethrin, bioresmethrin, cycloprothrin, cyfluthrin, beta beta-cyfluthrin), cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, cypermethrin, alpha-cypermethrin, betacypermethrin ( beta-cypermethrin), theta-cypermethrin, theta-cypermethrin, sigma-cypermethrin, cyphenothrin, deltamethrin, empenthrin, esf Enfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, fluvalinate, tau-fluvalinate ), Halfenprox, heptafluthrin, imiprothrin, kadethrin, meperfluthrin, momfluorothrin, permethrin, phenothrin, praothrin prallethrin), pyrethrin (pyrethrins), resmethrin (resmethrin), silafluofen (silafluofen), tefluthrin (tefluthrin), kappa-tefluthrin, tetramethrin (tetramethrin), tetramethi Flutrin (tetramethylfluthrin), tralomethrin (tralomethrin), transfluthrin (transfluthrin), benfluthrin (benfluthrin), flufenprox (flufenoprox), flumerin (flumethrin), framethrin (furamethrin), methfluthrin (metofluthrin), profluthrin and profluthrin (profluthrin) A group of sodium channel modulators consisting of (dimefluthrin).
Subgroup a-3:
GABAergic chloride channel blocker consisting of ethiprole, fipronil and flufiprole, and GABA consisting of afoxalaner, fluralaner, broflanilide and fluxametamide A group of agonistic chloride channel allosteric modulators.
Subgroup a-4:
Group of ryanodine receptor modulators consisting of chlorantraniliprole, cyantraniliprole, cyclaniliprole, flubendiamide, tetraniliprole and cyhalodiamide .
Subgroup a-5:
Alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl (NAC), carbofuran, carbofuran Fan (carbosulfan), ethiofencarb (fthiobucarb), fenobucarb (BPMC), formethanate (formetanate), furathiocarb (furathiocarb), isoprocarb (isoprocarb: MIPC), methiocarb (methiocarb), methomyl (methomyl), metolcarb (MTMC) , Oxamyl, pirimicarb, propoxur (PHC), thiodicarb, thiofanox, triazamate, trimethacarb, XMC and xylica Bed (xylylcarb: MPMC) consists, the group of carbamates acetylcholinesterase (AChE) inhibitors.
Subgroup a-6:
A group of nematicidal active compounds consisting of abamectin, fluensulfone, tioxazafen, and fluazaindolizine.
Subgroup a-7:
Mycorrhiza Fungi, Arthrobotrys dactyloides, Bacillus thuringiensis, Bacillus firmus, Bacillus megaterium, Bacillus amyloliquefaciens (Bacillus amyloliquefaciens), Hirsutella rhossiliensis, Hirsutella minnesotensis, Monacrosporium phymatopagus, Pasturiatransurie, Pasturiapass A group of microbial materials consisting of Pasteuria usgae, Verticillium chlamydosporium and Harpin protein.
Group (b):
A group consisting of the following subgroups b-1, b-2, b-3, b-4, b-5, b-6, b-7, b-8 and b-9.
Subgroup b-1:
Azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, dinicoazole, diniconazole-M, epiconconazole, ethaconazole (Etaconazole), fenarimol, fenbuconazole, fluquinconazole, quinconazole, flusilazole, flutriafol, hexaconazole, imazaril ( imazalil), imibenconazole, ipconazole, metconazole, microbutanil, nuarimol, oxpoconazole, o Spoconazole fumarate, pefurazoate, penconazole, prochloraz, propiconazole, prothioconazole, pyrifenox, pyrisoxazole ), Simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triflumizole, triforine and triticonazole A group of sterol biosynthesis inhibitors.
Subgroup b-2:
Azoxystrobin, coumoxystrobin, dimoxystrobin, enoxastrobin, famoxadone, fenamidone, fenaminstrobin, full Phenoxystrobin, fluoxastrobin, cresoxim-methyl, mandestrobin, metinominostrobin, orysastrobin, picoxystrobin , Pyraclostrobin, pyrametostrobin, pyraoxystrobin, trifloxystrobin, pyribencarb, triclopyricarb, triazopyricarb Consisting de (cyazofamid) and amisulbrom (amisulbrom), the group of Qo inhibitors (Quinone outside inhibitors).
Subgroup b-3:
A group of RNA polymerase I inhibitors consisting of benalaxyl, benalaxyl-M, furalaxyl, metalaxyl, metalaxyl-M, oxadixyl and ofurace .
Subgroup b-4:
Benodanil, benzovindiflupyr, bixafen, boscalid, carboxin, fenfuram, fluopyram, flutolanil, fluxapyroxad ), Furametpyr, isofetamid, isoprazam, mepronil, oxycarboxin, penthiopyrad, penflufen, sedaxane, thifluzamide, thifluamide (Pyraziflumid), pidiflumetofen (CAS registration number 1228284-64-7), 3-difluoromethyl-1-methyl-N- (1,1,3-trimethylindan-4-yl) pyrazole-4- Carboxamide (CAS registration No. 141573-94-6, hereinafter referred to as “bactericidal compound β1”), 3-difluoromethyl-1-methyl-N-[(3R) -1,1,3-trimethylindan-4-yl] pyrazole -4-carboxamide (CAS registration number 1352994-67-2, hereinafter sometimes referred to as “bactericidal compound β2”), 3-difluoromethyl-N- (7-fluoro-1,1,3-trimethylindan-4- Yl) -1-methylpyrazole-4-carboxamide (CAS registration number 1383809-87-7, hereinafter sometimes referred to as “bactericidal compound β3”), 3-difluoromethyl-N-[(3R) -7-fluoro- 1,1,3-trimethylindan-4-yl] -1-methylpyrazole-4-carboxamide (CAS registration number 1513466-73-3, hereinafter sometimes referred to as “bactericidal compound β4”) and N-cyclopropyl- 3- (Difluoromethyl) -5-fluoro-N- (5-chloro-2-isopropylbenzyl) -1-methyl-1H-pyrazole-4-carboxamide (CAS registration number 1255734-28-1, hereinafter referred to as “bactericidal compound β5”) A group of succinate dehydrogenase inhibitors.
Subgroup b-5:
It consists of benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate, thiophanate-methyl, diethofencarb, zoxamide and ethaboxam. A group of β-tubulin polymerization inhibitors.
Subgroup b-6:
Ferbam, mancozeb, manneb, maneb, metiram, propineb, thiram, zineb, ziram, captan, captafol ), Folpet, chlorothalonil, tolylfluanid, guazatine, iminoctadine, anilazine, dithianon, chinomethionate or quinomethionate fluoride A group of multi-acting point contact active compounds consisting of
Subgroup b-7:
Dimethomorph, flumorph, pyrimorph, benthiavalicarb, benthivalicarb-isopropyl, iprovalicarb, valifenalate and mandipropamid A group of cellulose synthesis inhibitors.
Subgroup b-8:
MAP (mitogen-activated protein) / histidine kinase inhibitor in osmotic signal transduction consisting of fenpiclonil, fludioxonil, clozolinate, iprodione, procymidone and vinclozolin group.
Subgroup b-9:
A group of other fungicides consisting of tolclofos-methyl, oxathiapiproline, picarbutrazox, fluopicolide and silthiofam.
[2]
The pest according to [1], wherein the content ratio of the compound represented by the formula (1) and one or more compounds selected from the group (a) is 100: 1 to 1: 100 by weight. Control composition.
[3]
The pest according to [1], wherein the content ratio of the compound represented by the formula (1) and one or more compounds selected from the group (a) is 10: 1 to 1:10 by weight. Control composition.
[4]
The pest according to [1], wherein the content ratio of the compound represented by the formula (1) and one or more compounds selected from the group (b) is 10,000: 1 to 1: 100 by weight. Control composition.
[5]
The pest according to [1], wherein the content ratio of the compound represented by the formula (1) and one or more compounds selected from the group (b) is 1000: 1 to 1:10 by weight. Control composition.
[6]
A pest control method comprising a step of applying an effective amount of the pest control composition according to any one of [1] to [5] to a pest or a habitat of the pest.
[7]
The pest control method which has the process of applying the effective amount of the pest control composition in any one of [1]-[5] to the plant, a plant seed, a bulb, or the soil which grows a plant.
[8]
Plant seeds or bulbs to which an effective amount of the pesticidal composition according to any one of [1] to [5] is attached.

  According to the present invention, pests can be controlled.

  The composition of the present invention contains the pyridazine compound and the compound.

Examples of substituents used in the description of the present specification will be described below.
The expression “may have one or more atoms or groups selected from group A” means that when it has two or more atoms or groups selected from group A, atoms selected from group A Alternatively, the groups may be the same as or different from each other.
In the present specification, the expression “may have one or more halogen atoms” means that when two or more halogen atoms are present, the halogen atoms may be the same or different from each other. Good.
The expression “having one or more halogen atoms”, when having two or more halogen atoms, may be the same as or different from each other.

  “Heterocyclic group” means a group containing at least one selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom in addition to a carbon atom as a ring-constituting atom, an aromatic heterocyclic group and a non-aromatic group Represents a heterocyclic group.

Examples of the “aromatic heterocyclic group” include 2-furyl group, 3-furyl group, 2-thienyl group, 3-thienyl group, 3-pyrazolyl group, 4-pyrazolyl group, 5-pyrazolyl group, 1-pyrrolyl. 5-membered aromatic heterocyclic groups such as a group, 1-pyrazolyl group, 1-imidazolyl group, 1,2,4-triazol-1-yl group; and 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, etc. A 6-membered aromatic heterocyclic group bonded at the carbon atom.

As the “3-7 membered non-aromatic heterocyclic group”, for example,
Aziridin-1-yl group, azetidin-1-yl group, pyrrolidin-1-yl group, 3,3,4,4-tetrafluoropyrrolidin-1-yl group, tetrahydrofuran-2-yl group, tetrahydrofuran-3-yl And non-aromatic heterocyclic groups such as a group, piperidin-1-yl group, morpholin-4-yl group, thiomorpholin-4-yl group, and azepan-1-yl group.

  “5- or 6-membered heteroaryl” represents a 5-membered aromatic heterocyclic group or a 6-membered aromatic heterocyclic group.

Examples of the “C2-C10 alkyl group” include an ethyl group, an isopropyl group, a propyl group, and a butyl group.
In the pyridazine compound, examples of the “C2-C10 haloalkyl group” include a 2-fluoroethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 2,2,2-trichloroethyl group, Pentafluoroethyl, heptafluoroisopropyl, 2,2,3,3-tetrafluoropropyl, 2,2,3,3,3-pentafluoropropyl, and 2,2,3,4,4,4 A hexafluorobutyl group.

Examples of the “C3-C10 alkenyl group” include a 2-propenyl group and a 3-butenyl group.
In the pyridazine compound, examples of the “C3-C10 haloalkenyl group” include a 3,3-difluoro-2-propenyl group, a 3,3-difluoro-2-propenyl group, and a 4,4-difluoro-3-butenyl group. Can be mentioned.

Examples of the “C3-C10 alkynyl group” include a 2-propynyl group and a 2-butynyl group.
Examples of the “C3-C10 haloalkynyl group” in the present pyridazine compound include a 3-chloro-2-propynyl group, a 3-fluoro-2-propynyl group, and a 4,4,4-trifluoro-2-butynyl group. It is done.

  "(C1-C5 alkyl) -O- (C2-C5 alkyl) group having one or more halogen atoms" means a group having one or more halogen atoms in a C1-C5 alkyl moiety and / or a C2-C5 alkyl moiety. For example, 2- (2,2,2-trifluoroethoxy) ethyl group and 1,1,1-trifluoro-3-methoxypropan-2-yl group can be mentioned.

  “(C3-C5 alkenyl) -O— (C2-C5 alkyl) having one or more halogen atoms” means a group having one or more halogen atoms in the C3-C5 alkenyl moiety and / or C2-C5 alkyl moiety. For example, 2- (3,3-difluoro-2-propenyloxy) ethyl group.

  "(C3-C5 alkynyl) -O- (C2-C5 alkyl) group having one or more halogen atoms" means a group having one or more halogen atoms in the C3-C5 alkynyl moiety and / or C2-C5 alkyl moiety. For example, 2- (4,4,4-trifluoro-2-butynyloxy) ethyl group.

"(C1-C5 alkyl) -S (O) _m- (C2-C5 alkyl) group having one or more halogen atoms" means one or more halogen atoms in the C1-C5 alkyl moiety and / or C2-C5 alkyl moiety. Represents a group having an atom, for example, 2- (trifluoromethylthio) ethyl group, 2- (trifluoromethylsulfinyl) ethyl group, 2- (trifluoromethylsulfonyl) ethyl group, 2- (2,2,2-trimethyl) Examples include fluoroethylthio) ethyl group, 2- (2,2,2-trifluoroethanesulfinyl) ethyl group, and 2- (2,2,2-trifluoroethanesulfonyl) ethyl group.

“(C1-C3 alkyl) -S (O) _y- (C1-C3 alkyl) group optionally having one or more halogen atoms” means a C1-C3 alkyl moiety and / or a C1-C3 alkyl moiety. Represents a group which may have one or more halogen atoms, for example, methylthiomethyl group, trifluoromethylthiomethyl group, methanesulfinylmethyl group, trifluoromethanesulfonylmethyl group, methanesulfonylmethyl group, 2- (methylthio) ethyl Group and ethylthiomethyl group.

"(C3-C5 alkenyl) -S (O) _m- (C2-C5 alkyl) group having one or more halogen atoms" means one or more halogen atoms in the C3-C5 alkenyl moiety and / or C2-C5 alkyl moiety. It represents a group having an atom, and examples thereof include 2- (3,3-difluoro-2-propenylthio) ethyl group.

"(C3-C5 alkynyl) -S (O) _m- (C2-C5 alkyl) group having one or more halogen atoms" means one or more halogen atoms in the C3-C5 alkenyl moiety and / or C2-C5 alkyl moiety. Represents a group having an atom, and examples thereof include 2- (4,4,4-trifluoro-2-butynylthio) ethyl group.

  "(C1-C5 alkyl) -C (O)-(C1-C5 alkyl) group having one or more halogen atoms" means any one C1-C5 alkyl moiety or both C1-C5 alkyl group moieties Represents a group having one or more halogen atoms, and examples thereof include a 3,3,3-trifluoro-2-oxopropyl group.

Examples of the “C1-C6 chain hydrocarbon group optionally having one or more halogen atoms” include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a pentyl group, a hexyl group, and trifluoromethyl. C1 which may have one or more halogen atoms such as a group, a trichloromethyl group, a 2-fluoroethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group and a pentafluoroethyl group -C6 alkyl group;
It may have one or more halogen atoms such as vinyl group, 1-propenyl group, 2-propenyl group, 1-methylvinyl group, 1-hexenyl group, 1,1-difluoroallyl group, pentafluoroallyl group, etc. -C6 alkenyl group; and C2 optionally having one or more halogen atoms such as ethynyl group, propargyl group, 3-butynyl group, 1-hexynyl group and 4,4,4-trifluoro-2-butynyl group -C6 alkynyl group is mentioned.

  Examples of the “phenyl group optionally having one or more atoms or groups selected from group A” include a phenyl group, a 2-fluorophenyl group, a 4-fluorophenyl group, a 2,3-difluorophenyl group, 2,3,4,5,6-pentafluorophenyl group, 4-chlorophenyl group, 4-bromophenyl group, 4-iodophenyl group, 4- (trifluoromethyl) phenyl group, 4- (trifluoromethoxy) phenyl Group, 4- (trifluoromethylsulfanyl) phenyl group, 4-cyanophenyl group, 4- (methylsulfinyl) phenyl group, and 4- (methylsulfonyl) phenyl group.

  As "any five-membered aromatic heterocyclic group selected from group B (the 5-membered aromatic heterocyclic group may have one or more atoms or groups selected from group A)". For example, pyrrol-1-yl group, 2-chloropyrrol-1-yl group, pyrazol-1-yl group, 3- (trifluoromethyl) pyrazol-1-yl group, 4-chloroimidazol-1-yl group, 1,2,4-triazol-1-yl group, 3-methoxy-1,2,4-triazol-1-yl group, 3-methylthio-1,2,4-triazol-1-yl group, 1,2 , 3-Triazol-1-yl group, oxazol-2-yl group, thiazol-2-yl group, 1,3,4-oxadiazol-2-yl group, 1,3,4-thiadiazol-2-yl Group, and 1,2,4-oxadiazol-3-yl group And the like.

  As “any 6-membered aromatic heterocyclic group selected from group C (the 6-membered aromatic heterocyclic group may have one or more atoms or groups selected from group A)”. For example, pyridin-2-yl group, pyridin-3-yl group, pyridin-4-yl group, 4-trifluoromethylpyridin-2-yl group, 2-chloropyridin-5-yl group, pyrimidin-2-yl Groups, pyrazin-2-yl groups, pyrimidin-4-yl groups, pyridazin-3-yl groups, pyrimidin-5-yl groups, and pyridazin-4-yl groups.

  "Any 3-7 membered non-aromatic heterocyclic group selected from group D (the 3-7 membered non-aromatic heterocyclic group is one or more selected from the group consisting of a halogen atom and a C1-C6 alkyl group" Examples of the term “which may have an atom or a group” include, for example, an aziridin-1-yl group, an azetidin-1-yl group, a pyrrolidin-1-yl group, and 3,3,4,4-tetrafluoropyrrolidine-1. -Yl group, piperidin-1-yl group, 4,4-dimethylpiperidin-1-yl group, and azepan-1-yl group.

  Examples of the “C3-C7 cycloalkyl group optionally having one or more halogen atoms” include a cyclopropyl group, a 2,2-difluorocyclopropan-1-yl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, And cycloheptyl group.

  “(C3-C7 cycloalkyl)-(C1-C3 alkyl) group optionally having one or more halogen atoms” represents a group having one or more halogen atoms in the C3-C7 cycloalkyl moiety; Examples include a cyclopropylmethyl group, a 2- (cyclopropyl) ethyl group, a (2,2-difluorocyclopropyl) methyl group, and a cyclopentylmethyl group.

  Examples of the “phenyl C1-C3 alkyl group (the phenyl portion of the phenyl C1-C3 alkyl group may have one or more atoms or groups selected from group A)” include, for example, a benzyl group, 2-fluoro Examples include benzyl group, 4-chlorobenzyl group, 4- (trifluoromethyl) benzyl group, and 2- (4- (trifluoromethyl) phenyl) ethyl group.

“(5- or 6-membered heteroaryl) C1-C3 alkyl group (the 5- or 6-membered heteroaryl) C1-C3 alkyl group has one or more atoms or groups selected from group A. May be included.) "Is, for example, (1-methylpyrrol-3-yl) methyl group, (oxazol-2-yl) methyl group, (tetrahydrofuran-3-yl) methyl group, (tetrahydrofuran-2) -Cyl group having one 5-membered aromatic heterocycle such as -yl) methyl group, 2- (1,2,4-triazol-1-yl) ethyl group, (2-chlorothiazol-5-yl) methyl group and the like. A C3 alkyl group; and (pyridin-2-yl) methyl group, (pyridin-4-yl) methyl group, (pyrimidin-2-yl) methyl group, (pyrimidin-4-yl) methyl group, C1-C3 alkyl groups having 1 6-membered aromatic heterocycle such as-(2-chloropyridin-5-yl) ethyl group and [2- (trifluoromethyl) pyridin-2-yl] methyl group It is done.

  Examples of the “C2-C6 alkoxycarbonyl group” include a methoxycarbonyl group and an ethoxycarbonyl group.

  "(C1-C3 alkyl) -O- (C1-C3 alkyl) group optionally having one or more halogen atoms" means any one C1-C3 alkyl moiety or both C1-C3 alkyl. A group having one or more halogen atoms in the group portion is represented, and examples thereof include a methoxymethyl group, an ethoxymethyl group, and a 2- (methoxy) ethyl group.

  Examples of the “C1-C6 alkoxy group optionally having one or more halogen atoms” include a trifluoromethoxy group and a 2,2,2-trifluoroethoxy group.

  "Halogen atom" represents a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

Examples of the pyridazine compound include the following compounds.

[Aspect 1] In the present pyridazine compound, R ¹ is a C2-C10 alkyl group, a C3-C10 alkenyl group, a (C1-C5 alkyl) -O- (C2-C5 alkyl) group, or (C1-C5 alkyl) -S. (O) _m- (C2-C5 alkyl) group (provided that the C2-C10 alkyl group, C3-C10 alkenyl group, (C1-C5 alkyl) -O- (C2-C5 alkyl) group, and (C1 -C5 _{alkyl) -S (O) m - (} C2-C5 alkyl) group having one or more halogen atoms), R ² and R ³ each independently have a hydrogen atom, one or more halogen atoms An optionally substituted C1-C6 alkyl group, or a halogen atom, R ⁴ is a C1-C6 alkyl group, p is 0 or 1, and when p is 1, R ⁵ is one or more halogen atoms Even if you have atoms A compound that is a good C1-C6 alkyl group.
[Aspect 2] In the pyridazine compound, R ¹ is a C2-C6 alkyl group having two or more fluorine atoms, and R ² and R ³ each independently have a hydrogen atom or one or more halogen atoms. An optionally substituted C1-C6 alkyl group, or a halogen atom, R ⁴ is a C1-C6 alkyl group, p is 0 or 1, and when p is 1, R ⁵ is one or more halogen atoms. The compound which is a C1-C6 alkyl group which may have.
[Aspect 3] In the pyridazine compound, R ¹ is a C2-C6 alkyl group having two or more fluorine atoms, and R ² and R ³ each independently have a hydrogen atom or one or more halogen atoms. An optionally substituted C1-C6 alkyl group, or a halogen atom, R ⁴ is an ethyl group, p is 0 or 1, and when p is 1, R ⁵ has one or more halogen atoms. A compound that is an optionally substituted C1-C6 alkyl group.
[Aspect 4] In the pyridazine compound, R ¹ is a C2-C10 alkyl group having two or more fluorine atoms, R ² and R ³ are hydrogen atoms, R ⁴ is an ethyl group, and p is 0 or 1. A compound in which, when p is 1, R ⁵ is a C1-C6 alkyl group optionally having one or more halogen atoms.
[Aspect 5] In the pyridazine compound, R ¹ is a C2-C10 haloalkyl group, and R ² and R ³ are each independently a hydrogen atom or a C1-C6 alkyl optionally having one or more halogen atoms. A C1-C6 chain which may be a group, or a halogen atom, R ⁴ may have one or more halogen atoms, and R ⁵ may have one or more halogen atoms Any 5-membered aromatic heterocyclic group selected from the formula hydrocarbon group and group B (the 5-membered aromatic heterocyclic group may have one or more atoms or groups selected from group A. ), Any 6-membered aromatic heterocyclic group selected from group C (the 6-membered aromatic heterocyclic group may have one or more atoms or groups selected from group A), group Any 3-7-membered non-aromatic heterocyclic group selected from D (the 3-7-membered non-aromatic group) The aromatic heterocyclic group may have one or more atoms or groups selected from the group consisting of halogen atoms and C1-C6 alkyl groups.), OR ⁷ , NR ⁸ R ⁹ , S (O) _y R ¹² , or a halogen atom, and p is 0, 1, 2, or 3 (provided that when p represents 2 or 3, a plurality of R ⁵ may be the same or different from each other).
[Aspect 6] In this pyridazine compound, A is a nitrogen atom, R ¹ is a C2-C10 haloalkyl group, R ² and R ³ are hydrogen atoms, R ⁴ is an ethyl group, and R ⁵ is 1 A C1-C6 alkyl group optionally having the above halogen atom, and p is 0, 1, 2 or 3 (provided that when p represents 2 or 3, a plurality of R ^{5 s} are the same or different from each other) A compound that is)
[Aspect 7] A compound in which A is a nitrogen atom or CR ⁶ in aspects 1 to 5.
[Aspect 8] A compound in which A is a nitrogen atom or CH in aspects 1 to 5.
[Aspect 9] A compound according to Aspects 1 to 5, wherein A is a nitrogen atom.
[Aspect 10] A compound in which A is CR ⁶ in aspects 1 to 5.
[Aspect 11] A compound in which A is CH in aspects 1 to 5.

において、Ｑ¹は、Ｎ⁺−Ｏ^-又は窒素原子であり、Ｑ²は、Ｎ⁺−Ｏ^-、ＣＲ^6N、又は窒素原子であり、Ｑ¹又はＱ²のいずれか一方が、必ずＮ⁺−Ｏ^-であり、Ｒ^6Nは、水素原子、又はハロゲン原子であり、Ｒ^1Nは、Ｃ２−Ｃ１０ハロアルキル基であり、Ｒ^2NおよびＲ^3Nは、それぞれ独立して、水素原子、１以上のハロゲン原子を有していてもよいＣ１−Ｃ３アルキル基、又はハロゲン原子であり、Ｒ^4Nは、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルキル基であり、ｑは、０、又は１であり、ｑが１の場合に、Ｒ^5Nが、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルキル基である化合物。
〔態様１３〕態様１２において、Ｒ^1Nが、Ｃ２−Ｃ１０ハロアルキル基であり、Ｒ^2NおよびＲ^3Nが、水素原子であり、Ｒ^4Nが、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルキル基であり、ｑが、０、又は１であり、ｑが１の場合に、Ｒ^5Nが、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルキル基である化合物。
〔態様１４〕態様１２において、Ｒ^1Nが、Ｃ２−Ｃ１０ハロアルキル基であり、Ｒ^2NおよびＲ^3Nが、水素原子であり、Ｒ^4Nが、エチル基であり、ｑが、０、又は１であり、ｑが１の場合に、Ｒ^5Nが、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルキル基である化合物。
〔態様１５〕態様１２〜１４において、Ｑ¹がＮ⁺−Ｏ^-であり、Ｑ²がＮ⁺−Ｏ^-、ＣＨ、ＣＦ、又は窒素原子である化合物。
〔態様１６〕態様１２〜１４において、Ｑ¹がＮ⁺−Ｏ^-であり、Ｑ²が窒素原子、又はＣＨである化合物。
〔態様１７〕態様１２〜１４において、Ｑ¹がＮ⁺−Ｏ^-であり、Ｑ²が窒素原子である化合物。
〔態様１８〕態様１２〜１４において、Ｑ¹及びＱ²がＮ⁺−Ｏ^-である化合物。
〔態様１９〕態様１２〜１４において、Ｑ¹がＮ⁺−Ｏ^-であり、Ｑ²がＣＲ^6Nである化合物。 Examples of the N oxide compound include the following compounds.
[Aspect 12] Formula (1-N)

Q ¹ is N ⁺ —O ⁻ or a nitrogen atom, Q ² is N ⁺ —O ⁻ , CR ^6N , or a nitrogen atom, and either Q ¹ or Q ² is always N ⁺ —O 2 ^— , R ^6N is a hydrogen atom or a halogen atom, R ^1N is a C2-C10 haloalkyl group, R ^2N and R ^3N are each independently a hydrogen atom, one or more halogen atoms A C1-C3 alkyl group optionally having an atom, or a halogen atom, R ^4N is a C1-C6 alkyl group optionally having one or more halogen atoms, and q is 0, or 1. A compound in which when R is 1 and q is 1, R ^5N is a C1-C6 alkyl group optionally having one or more halogen atoms.
[Aspect 13] In Aspect 12, R ^1N is a C2-C10 haloalkyl group, R ^2N and R ^3N are hydrogen atoms, and R ^4N may have one or more halogen atoms. A compound, which is a C6 alkyl group, q is 0 or 1, and R ^5N is a C1-C6 alkyl group optionally having one or more halogen atoms when q is 1.
[Aspect 14] In Aspect 12, R ^1N is a C2-C10 haloalkyl group, R ^2N and R ^3N are a hydrogen atom, R ^4N is an ethyl group, and q is 0 or 1. , Q is 1, a compound in which R ^5N is a C1-C6 alkyl group optionally having one or more halogen atoms.
[Aspect 15] A compound according to Aspects 12 to 14, wherein Q ¹ is N ⁺ —O ⁻ and Q ² is N ⁺ —O ⁻ , CH, CF, or a nitrogen atom.
[Aspect 16] A compound according to Aspects 12 to 14, wherein Q ¹ is N ⁺ —O ⁻ and Q ² is a nitrogen atom or CH.
[Aspect 17] A compound according to Aspects 12 to 14, wherein Q ¹ is N ⁺ —O ⁻ and Q ² is a nitrogen atom.
[Aspect 18] A compound according to Aspects 12 to 14, wherein Q ¹ and Q ² are N ⁺ —O ⁻ .
[Aspect 19] A compound according to Aspect 12-14, wherein Q ¹ is N ⁺ —O ⁻ and Q ² is CR ^6N .

  Next, the manufacturing method of this pyridazine compound is demonstrated.

  The pyridazine compound and the intermediate compound can be produced, for example, according to the following production methods 1 to 12.

［式中、記号は前記と同じ意味を表す。］ Manufacturing method 1
The present pyridazine compound (1b) in which n = 1 in the formula (1) (hereinafter referred to as the present pyridazine compound (1b)), and the present pyridazine compound (1c) in which n = 2 in the formula (1) (hereinafter referred to as the present). The pyridazine compound (1c) is prepared by reacting the present pyridazine compound (1a) (hereinafter referred to as the present pyridazine compound (1a)) in which n = 0 in the formula (1) with an oxidizing agent. be able to.

[Wherein the symbols have the same meaning as described above. ]

First, a method for producing the pyridazine compound (1b) from the pyridazine compound (1a) will be described.
The reaction is usually performed in the presence of a solvent. Examples of the solvent used in the reaction include halogenated hydrocarbons such as dichloromethane and chloroform (hereinafter referred to as halogenated hydrocarbons).
Examples of the oxidizing agent used in the reaction include m-chloroperbenzoic acid (hereinafter referred to as mCPBA).
For the reaction, the oxidizing agent is usually used at a ratio of 1 to 1.2 mol per 1 mol of the present pyridazine compound (1a).
The reaction temperature is usually in the range of -20 to 80 ° C. The reaction time is usually in the range of 0.1 to 12 hours.
After completion of the reaction, water is added to the reaction mixture and extracted with an organic solvent, and the organic layer is extracted with an aqueous solution of a reducing agent (for example, sodium sulfite, sodium thiosulfate) and an aqueous solution of a base (for example, sodium bicarbonate) as necessary. Wash. This pyridazine compound (1b) can be obtained by drying and concentrating the organic layer.

Next, a method for producing the pyridazine compound (1c) from the pyridazine compound (1b) will be described.
The reaction is usually performed in the presence of a solvent. Examples of the solvent used for the reaction include halogenated hydrocarbons.
Examples of the oxidizing agent used in the reaction include mCPBA.
For the reaction, the oxidizing agent is usually used at a ratio of 1 to 2 mol with respect to 1 mol of the present pyridazine compound (1b).
The reaction temperature is usually in the range of -20 to 120 ° C. The reaction time is usually in the range of 0.1 to 12 hours.
After completion of the reaction, water is added to the reaction mixture and extracted with an organic solvent, and the organic layer is extracted with an aqueous solution of a reducing agent (for example, sodium sulfite, sodium thiosulfate) and an aqueous solution of a base (for example, sodium bicarbonate) as necessary. Wash. The pyridazine compound (1c) can be obtained by drying and concentrating the organic layer.

Moreover, this pyridazine compound (1c) can be manufactured by one-step reaction (one pot) by making this pyridazine compound (1a) and an oxidizing agent react.
The reaction is usually performed in the presence of a solvent. Examples of the solvent used for the reaction include halogenated hydrocarbons.
Examples of the oxidizing agent used in the reaction include mCPBA.
For the reaction, the oxidizing agent is usually used at a ratio of 2 to 3 moles relative to 1 mole of the present pyridazine compound (1a).
The reaction temperature is usually in the range of 0 to 120 ° C. The reaction time is usually in the range of 0.1 to 12 hours.
After completion of the reaction, water is added to the reaction mixture and extracted with an organic solvent, and the organic layer is extracted with an aqueous solution of a reducing agent (for example, sodium sulfite, sodium thiosulfate) and an aqueous solution of a base (for example, sodium bicarbonate) as necessary. Wash. By drying and concentrating the organic layer, the pyridazine compound (1c) can be obtained.

［式中、Ｖはハロゲン原子を表し、その他の記号は前記と同じ意味を表す。］
該反応は、通常溶媒の存在下で行われる。反応に用いられる溶媒としては、例えばジメチルホルムアミド（以下、ＤＭＦと記す。）、Ｎ−メチルピロリドン（以下、ＮＭＰと記す。）、ジメチルスルホキシド（以下、ＤＭＳＯと記す。）等の非プロトン性極性溶媒（以下、非プロトン性極性溶媒と記す。）が挙げられる。
反応に用いられる塩基としては、水素化ナトリウム等のアルカリ金属水素化物類（以下、アルカリ金属水素化物類と記す。）が挙げられる。
反応には、化合物（Ｍ１）１モルに対して、化合物（Ｒ１）が通常１〜１０モルの割合、塩基が通常１〜１０モルの割合で用いられる。
反応温度は、通常−２０℃〜１５０℃の範囲である。反応時間は通常０．５〜２４時間の範囲である。
反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、本ピリダジン化合物（１ａ）を得ることができる。
該反応において、Vはフッ素原子又は塩素原子が好ましい。 Manufacturing method 2
This pyridazine compound (1a) is based on a compound represented by formula (M1) (hereinafter referred to as compound (M1)) and a compound represented by formula (R1) (hereinafter referred to as compound (R1)). It can manufacture by making it react in presence of.

[Wherein V represents a halogen atom, and other symbols have the same meaning as described above. ]
The reaction is usually performed in the presence of a solvent. Examples of the solvent used in the reaction include aprotic polar solvents such as dimethylformamide (hereinafter referred to as DMF), N-methylpyrrolidone (hereinafter referred to as NMP), dimethyl sulfoxide (hereinafter referred to as DMSO), and the like. (Hereinafter referred to as aprotic polar solvent).
Examples of the base used in the reaction include alkali metal hydrides such as sodium hydride (hereinafter referred to as alkali metal hydrides).
In the reaction, with respect to 1 mole of the compound (M1), the compound (R1) is usually used at a ratio of 1 to 10 moles, and the base is usually used at a ratio of 1 to 10 moles.
The reaction temperature is usually in the range of -20 ° C to 150 ° C. The reaction time is usually in the range of 0.5 to 24 hours.
After completion of the reaction, the pyridazine compound (1a) can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
In the reaction, V is preferably a fluorine atom or a chlorine atom.

［式中、Ｖ¹はＣ１−Ｃ１０ペルフルオロアルカンスルホニルオキシ基を表し、その他の記号は前記と同じ意味を表す。］
該反応は、通常溶媒の存在下で行われる。反応に用いられる溶媒としては、例えば非プロトン性極性溶媒が挙げられる。
反応に用いられる塩基としては、例えば炭酸カリウム、炭酸セシウム等のアルカリ金属炭酸塩類（以下、アルカリ金属炭酸塩類と記す。）が挙げられる。
反応には、化合物（Ｍ２）１モルに対して、化合物（Ｒ２）が通常１〜１０モルの割合、塩基が通常０．１〜５モルの割合で用いられる。
反応温度は、通常−２０℃〜１２０℃の範囲である。反応時間は通常０．１〜２４時間の範囲である。
該反応では、式（Ｂ１）で示される化合物が副生することもある。
反応終了後は、反応混合物を水に加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、本ピリダジン化合物（１）を得ることができる。 Production method 3
The pyridazine compound (1) includes a compound represented by formula (M2) (hereinafter referred to as compound (M2)) and a compound represented by formula (R2) (hereinafter referred to as compound (R2)). It can be produced by reacting in the presence of a base.

[Wherein, V ¹ represents a C1-C10 perfluoroalkanesulfonyloxy group, and other symbols have the same meaning as described above. ]
The reaction is usually performed in the presence of a solvent. Examples of the solvent used for the reaction include aprotic polar solvents.
Examples of the base used for the reaction include alkali metal carbonates such as potassium carbonate and cesium carbonate (hereinafter referred to as alkali metal carbonates).
In the reaction, with respect to 1 mole of the compound (M2), the compound (R2) is usually used at a ratio of 1 to 10 moles, and the base is usually used at a ratio of 0.1 to 5 moles.
The reaction temperature is usually in the range of -20 ° C to 120 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
In the reaction, the compound represented by the formula (B1) may be by-produced.
After completion of the reaction, the pyridazine compound (1) can be obtained by performing post-treatment operations such as adding the reaction mixture to water, extracting with an organic solvent, and drying and concentrating the organic layer.

［式中、Ｖ²はハロゲン原子又はメタンスルホニル基を表し、その他の記号は前記と同じ意味を表す。］
該反応は、通常溶媒の存在下で行われる。反応に用いられる溶媒としては、例えば非プロトン性極性溶媒が挙げられる。
反応に用いられる塩基としては、例えばアルカリ金属炭酸塩類、アルカリ金属水素化物類が挙げられる。
反応には、化合物（Ｍ３）１モルに対して、化合物（Ｒ３）が通常１〜１００モルの割合、塩基が通常１〜１０モルの割合で用いられる。
反応温度は、通常−２０℃〜１５０℃の範囲である。反応時間は通常０．５〜２４時間の範囲である。
反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、本ピリダジン化合物（１）を得ることができる。
該反応において、Ｖ²は塩素原子、又はメチルスルホニル基が好ましい。 Manufacturing method 4
The pyridazine compound (1) includes a compound represented by formula (M3) (hereinafter referred to as compound (M3)) and a compound represented by formula (R3) (hereinafter referred to as compound (R3)). It can be produced by reacting in the presence of a base.

[Wherein V ² represents a halogen atom or a methanesulfonyl group, and other symbols have the same meaning as described above. ]
The reaction is usually performed in the presence of a solvent. Examples of the solvent used for the reaction include aprotic polar solvents.
Examples of the base used for the reaction include alkali metal carbonates and alkali metal hydrides.
For the reaction, the compound (R3) is usually used in a proportion of 1 to 100 mol and the base is usually used in a proportion of 1 to 10 mol with respect to 1 mol of the compound (M3).
The reaction temperature is usually in the range of -20 ° C to 150 ° C. The reaction time is usually in the range of 0.5 to 24 hours.
After completion of the reaction, the pyridazine compound (1) can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
In the reaction, V ² is preferably a chlorine atom or a methylsulfonyl group.

［式中、記号は前記と同じ意味を表す。］
該反応は、化合物（Ｍ２）に代えて化合物（Ｍ４）を用いることにより、製造法３に記載の方法に準じて実施することができる。
該反応では、式（Ｂ２）で示される化合物が副生することもある。 Manufacturing method 5
Compound (M1) can be produced by reacting a compound represented by formula (M4) (hereinafter referred to as compound (M4)) with compound (R2) in the presence of a base.

[Wherein the symbols have the same meaning as described above. ]
This reaction can be carried out according to the method described in Production Method 3 by using compound (M4) instead of compound (M2).
In the reaction, the compound represented by the formula (B2) may be by-produced.

［式中、Ｖ³はハロゲン原子を表し、Ｍは−Ｂ（ＯＨ）₂、４，４，５，５−テトラメチル−１，３，２−ジオキサボロラン−２−イル基、−ＳｎＢｕ₃、−ＺｎＣｌ、−ＭｇＣｌ、又は−ＭｇＢｒを表し、その他の記号は前記と同じ意味を表す。］
化合物（Ｍ６）は、例えば米国特許出願公開第２０１０／０２６１７２７号明細書に記載の方法に準じて製造することができる。
化合物（Ｍ７）は、例えば国際公開第０３／０２４９６１号記載の方法、又はOrganic Process Research & Development, 2004, 8, 192-200記載の方法に準じて製造することができる。
該反応は、通常溶媒の存在下で行われる。反応に用いられる溶媒としては、例えばエチレングリコールジメチルエーテル（以下、ＤＭＥと記す。）等のエーテル類（以下、エーテル類と記す。）、トルエン、キシレン等の芳香族炭化水素類（以下、芳香族炭化水素類と記す。）、非プロトン性極性溶媒、水及びこれらの混合物が挙げられる。
反応に用いられる金属触媒としては、テトラキストリフェニルホスフィンパラジウム（０）、１，１’−ビス（ジフェニルホスフィノ）フェロセン−パラジウム（ＩＩ）ジクロリド、トリス（ジベンジリデンアセトン）ジパラジウム（０）、酢酸パラジウム（ＩＩ）等のパラジウム触媒、ビス（シクロオクタジエン）ニッケル（０）、塩化ニッケル（ＩＩ）等のニッケル触媒、ヨウ化銅（Ｉ）、塩化銅（Ｉ）等の銅触媒等が挙げられる。
該反応は必要に応じて、配位子、塩基及び無機ハロゲン化物を加えてもよい。
反応に用いられる配位子としては、トリフェニルホスフィン、キサントホス、２，２’−ビス（ジフェニルホスフィノ）−１，１’−ビナフチル、１，１’−ビス（ジフェニルホスフィノ）フェロセン、２−ジシクロヘキシルホスフィノ−２’，４’，６’−トリイソプロピルビフェニル、２−ジシクロヘキシルホスフィノ−２’，６’−ジメトキシビフェニル、１，２−ビス（ジフェニルホスフィノ）エタン、２，２’−ビピリジン、２−アミノエタノール、８−ヒドロキシキノリン、１，１０−フェナントロリン等が挙げられる。
反応に用いられる塩基としては、例えばアルカリ金属水素化物類、アルカリ金属炭酸塩類、又はトリエチルアミン、ジイソピロピルエチルアミン、ピリジン、４−ジメチルアミノピリジン等の有機塩基類が挙げられる。
反応に用いられる無機ハロゲン化物としては、フッ化カリウム、フッ化ナトリウム等のアルカリ金属フッ素塩、塩化リチウム、塩化ナトリウム等のアルカリ金属塩素塩等が挙げられる。
反応には、化合物（Ｍ６）１モルに対して、化合物（Ｍ７）が通常１〜１０モルの割合、金属触媒が通常０．０１〜０．５モルの割合、配位子が通常０．０１〜１モルの割合、塩基が通常０．１〜５モルの割合、無機ハロゲン化物が通常０．１〜５モルの割合で用いられる。
反応温度は、通常−２０℃〜２００℃の範囲である。反応時間は通常０．１〜２４時間の範囲である。
反応終了後は、反応混合物を水に加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより化合物（Ｍ１）を得ることができる。
該反応において、V³は塩素原子、臭素原子又はヨウ素原子が好ましい。 Manufacturing method 6
The compound (M1) includes a compound represented by the formula (M6) (hereinafter referred to as the compound (M6)) and a compound represented by the formula (M7) (hereinafter referred to as the compound (M7)) as a metal catalyst. It can manufacture by making it react in presence of.

[Wherein V ³ represents a halogen atom, M represents —B (OH) ₂ , 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl group, —SnBu ₃ , — ZnCl, -MgCl, or -MgBr is represented, and other symbols have the same meaning as described above. ]
Compound (M6) can be produced, for example, according to the method described in US Patent Application Publication No. 2010/0261727.
Compound (M7) can be produced, for example, according to the method described in WO 03/024961 or the method described in Organic Process Research & Development, 2004, 8, 192-200.
The reaction is usually performed in the presence of a solvent. Examples of the solvent used in the reaction include ethers such as ethylene glycol dimethyl ether (hereinafter referred to as DME) (hereinafter referred to as ethers), aromatic hydrocarbons such as toluene and xylene (hereinafter referred to as aromatic carbonization). And aprotic polar solvent, water, and a mixture thereof.
Examples of the metal catalyst used in the reaction include tetrakistriphenylphosphine palladium (0), 1,1′-bis (diphenylphosphino) ferrocene-palladium (II) dichloride, tris (dibenzylideneacetone) dipalladium (0), acetic acid. Palladium catalysts such as palladium (II), nickel catalysts such as bis (cyclooctadiene) nickel (0), nickel (II) chloride, copper catalysts such as copper (I) iodide, copper (I) chloride, etc. .
In the reaction, a ligand, a base and an inorganic halide may be added as necessary.
Examples of the ligand used in the reaction include triphenylphosphine, xanthophos, 2,2′-bis (diphenylphosphino) -1,1′-binaphthyl, 1,1′-bis (diphenylphosphino) ferrocene, 2- Dicyclohexylphosphino-2 ′, 4 ′, 6′-triisopropylbiphenyl, 2-dicyclohexylphosphino-2 ′, 6′-dimethoxybiphenyl, 1,2-bis (diphenylphosphino) ethane, 2,2′-bipyridine , 2-aminoethanol, 8-hydroxyquinoline, 1,10-phenanthroline and the like.
Examples of the base used for the reaction include alkali metal hydrides, alkali metal carbonates, or organic bases such as triethylamine, diisopropylpyroethylamine, pyridine, and 4-dimethylaminopyridine.
Examples of the inorganic halide used in the reaction include alkali metal fluorine salts such as potassium fluoride and sodium fluoride, and alkali metal chlorine salts such as lithium chloride and sodium chloride.
In the reaction, with respect to 1 mol of the compound (M6), the compound (M7) is usually in a proportion of 1 to 10 mol, the metal catalyst is usually in a proportion of 0.01 to 0.5 mol, and the ligand is usually 0.01. ˜1 mol, base is usually used in a proportion of 0.1 to 5 mol, and inorganic halide is usually used in a proportion of 0.1 to 5 mol.
The reaction temperature is usually in the range of -20 ° C to 200 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (M1) can be obtained by performing post-treatment operations such as addition of the reaction mixture to water, extraction with an organic solvent, and drying and concentration of the organic layer.
In the reaction, V ³ is preferably a chlorine atom, a bromine atom or an iodine atom.

［式中、Ｖはハロゲン原子を表し、その他の記号は式（１）と同じ意味を表す。］ Manufacturing method 7
Among the compounds (M2), the compound (M2a) where n = 0, the compound (M2b) where n = 1, and the compound (M2c) where n = 2 can be produced according to the following method.

[Wherein V represents a halogen atom, and other symbols have the same meaning as in formula (1). ]

First, a method for producing the compound (M2a) from the compound (M4) will be described.
Compound (M2a) can be produced according to the method described in Production Method 2 by using compound (M4) instead of compound (M1).

Subsequently, a method for producing the compound (M2b) from the compound (M2a) and the compound (M2c) from the compound (M2b) will be described.
Compound (M2b) can be produced according to the method described in Production Method 1 by using compound (M2a) instead of compound (1a).
Compound (M2c) can be produced according to the method described in Production Method 1 by using compound (M2b) in place of compound (1b).

［式中、Ｒは、水素原子、メチル基、又はエチル基を表し、その他の記号は前記と同じ意味を表す。］
化合物（Ｍ８）は、例えばJournal of American Chemical Society, 2012, 134(6),2906-2909、又は国際公開第２０１４／０１０９９０号に記載の方法に準じて製造することができる。 Manufacturing method 8
The compound (M2) includes a compound represented by the formula (M8) (hereinafter referred to as the compound (M8)) and a compound represented by the formula (R4) (hereinafter referred to as the compound (R4)) as a base. Or by reacting in the presence of an acid, and then reacting the obtained compound with hydrazine.

[Wherein, R represents a hydrogen atom, a methyl group, or an ethyl group, and other symbols have the same meaning as described above. ]
Compound (M8) can be produced, for example, according to the method described in Journal of American Chemical Society, 2012, 134 (6), 2906-2909, or International Publication No. 2014/010990.

The reaction is usually performed in the presence of a solvent. Examples of the solvent used in the reaction include alcohols such as methanol and ethanol (hereinafter referred to as alcohols), ethers, aprotic polar solvents, water, and mixtures thereof.
Examples of the base used in the reaction include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide.
Examples of the acid used for the reaction include carboxylic acids such as acetic acid and formic acid, and mineral acids such as hydrochloric acid and sulfuric acid.
In the reaction, with respect to 1 mole of the compound (M8), the compound (R4) is usually in a proportion of 1 to 10 moles, the base is usually in a proportion of 1 to 10 moles, the acid is usually in a proportion of 1 to 10 moles, and the hydrazine is usually in a proportion. Used in a proportion of 1 to 10 mol.
The reaction temperature is usually in the range of -20 ° C to 150 ° C. The reaction time is usually in the range of 0.5 to 24 hours.
After completion of the reaction, the compound (M2) can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.

［式中、記号は前記と同じ意味を表す。］
化合物（Ｍ３ｂ）は、化合物（１ａ）に代えて化合物（Ｍ３ａ）を用いることにより、製造法１に記載の方法に準じて製造することができる。
化合物（Ｍ３ｃ）は、化合物（１ｂ）に代えて化合物（Ｍ３ｂ）を用いることにより、製造法１に記載の方法に準じて製造することができる。 Manufacturing method 9
Among the compounds (M3), the compound (M3b) where n = 1 and the compound (M3c) where n = 2 react the compound (M3a) where n = 0 among the compounds (M3) and an oxidizing agent. Can be manufactured.

[Wherein the symbols have the same meaning as described above. ]
Compound (M3b) can be produced according to the method described in Production Method 1 by using compound (M3a) instead of compound (1a).
Compound (M3c) can be produced according to the method described in Production Method 1 by using compound (M3b) instead of compound (1b).

［式中、Ｖ⁴は塩素原子又は臭素原子を表し、その他の記号は前記と同じ意味を表す。］ Manufacturing method 10
Among the compounds (M3), a compound (M3d) in which V ² is a chlorine atom or a bromine atom and a compound (M3e) in which V ² is a methylsulfonyl group can be produced according to the following method.

[Wherein, V ⁴ represents a chlorine atom or a bromine atom, and other symbols have the same meaning as described above. ]

First, a method for producing the compound (M3d) from the compound (M2) will be described.
Compound (M3d) can be produced by reacting compound (M2) with a halogenating agent.
The reaction is usually performed in the presence of a solvent. Aromatic hydrocarbons are mentioned as a solvent used for reaction.
Examples of the halogenating agent used in the reaction include phosphorus oxychloride and phosphorus oxybromide.
In the reaction, a catalyst may be added as necessary. Examples of the catalyst used for the reaction include DMF.
In the reaction, with respect to 1 mol of the compound (M2), the halogenating agent is usually used in a proportion of 1 to 10 mol, and the catalyst is usually used in a proportion of 0.01 to 0.1 mol. In the reaction, phosphorus oxychloride can also be used as a solvent.
The reaction temperature is usually in the range of -20 ° C to 150 ° C. The reaction time is usually in the range of 0.5 to 24 hours.
After completion of the reaction, the excess halogenating agent is distilled off under reduced pressure, water is added, and the resulting mixture is extracted with an organic solvent, and the organic layer is dried and concentrated. M3d) can be obtained.

Subsequently, a method for producing the compound (M3e) from the compound (M3d) will be described.
Compound (M3e) can be produced by reacting compound (M3d) with sodium methanesulfinate.
The reaction is usually performed in the presence of a solvent. Examples of the solvent used for the reaction include aprotic polar solvents.
In the reaction, a catalyst may be added as necessary. Examples of the catalyst used for the reaction include quaternary ammonium salts such as tetrabutylammonium chloride.
In the reaction, with respect to 1 mol of the compound (M3d), sodium methanesulfinate is usually used in a proportion of 1 to 10 mol, and the catalyst is usually used in a proportion of 0.01 to 0.5 mol.
The reaction temperature is usually in the range of -20 ° C to 150 ° C. The reaction time is usually in the range of 0.5 to 24 hours.
After completion of the reaction, the compound (M3e) can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.

［式中、Ｒ^xはメチル基又はエチル基を表し、その他の記号は前記と同じ意味を表す。］
化合物（Ｍ１０）は、例えば米国特許出願公開第２０１０／０２６１７２７号明細書に記載の方法に準じて製造することができる。 Manufacturing method 11
Compound (M4) can be produced, for example, according to the following method.

[Wherein R ^x represents a methyl group or an ethyl group, and other symbols represent the same meaning as described above. ]
Compound (M10) can be produced, for example, according to the method described in US Patent Application Publication No. 2010/0261727.

First, a method for producing a compound represented by formula (M9) (hereinafter referred to as compound (M9)) will be described.
Compound (M9) can be produced according to the method described in production method 6 using the compound represented by formula (M10) (hereinafter referred to as compound (M10)) instead of compound (M6). .

Then, it describes about the method of manufacturing a compound (M4) from a compound (M9).
Compound (M4) can be produced by reacting compound (M9) in the presence of an acid.
The reaction is usually performed in the presence of a solvent. Examples of the solvent used for the reaction include aromatic hydrocarbons, alcohols, acetic acid, water, and mixtures thereof.
Examples of the acid used for the reaction include mineral acids such as hydrochloric acid.
For the reaction, the acid is usually used at a ratio of 0.1 to 10 mol per 1 mol of the compound (M9). In the reaction, mineral acids can also be used as a solvent.
The reaction temperature is usually in the range of -20 ° C to 150 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the reaction mixture is added to water, extracted with an organic solvent, and the organic layer is concentrated; the reaction mixture is added to water and the resulting solid is collected by filtration; or the solid formed in the reaction mixture is filtered. The compound (M4) can be obtained by collecting by

［式中、記号は前記と同じ意味を表す。］
化合物（Ｍ１１）は、公知の化合物であるか、公知の方法、例えば国際公開第２０１４／０１０９９０号記載の方法に準じて製造することができる。 Production method 12
In compound (M8), compound (M8a) where n = 0, compound (M8b) where n = 1, and compound (M8c) where n = 2 can be produced, for example, according to the following method.

[Wherein the symbols have the same meaning as described above. ]
Compound (M11) is a known compound, or can be produced according to a known method, for example, the method described in International Publication No. 2014/010990.

First, a method for producing the compound (M8a) from the compound represented by the formula (M11) (hereinafter referred to as the compound (M11)) will be described.
Compound (M8a) can be produced according to the method described in Production Method 2 by using compound (M11) instead of compound (M1).

Subsequently, a method for producing a compound (M8b) from the compound (M8a) and a compound (M8c) from the compound (M8b) will be described.
Compound (M8b) can be produced according to the method described in Production Method 1 by using compound (M8a) instead of compound (1a).
Compound (M8c) can be produced according to the method described in Production Method 1 by using compound (M8b) instead of compound (1b).

［式中、記号は前記と同じ意味を表す。］
該反応は、化合物（１ａ）に代えて本ピリダジン化合物（１ｄＮ）を用い、酸化剤を本ピリダジン化合物（１ｄＮ）１モルに対して１．５〜２０モルの割合で用いること以外は製造法１に記載の方法に準じて実施することができる。 Production method 13
N oxide compound represented by formula (N11) (hereinafter referred to as N oxide compound (N11)), N oxide compound represented by formula (N12) (hereinafter referred to as N oxide compound (N12)), formula (N The N oxide compound represented by N13) (hereinafter referred to as N oxide compound (N13)) is a pyridazine compound represented by formula (1dN) (hereinafter referred to as present pyridazine compound (1dN)) and an oxidizing agent. It can manufacture by making these react.

[Wherein the symbols have the same meaning as described above. ]
In this reaction, the present pyridazine compound (1dN) is used in place of the compound (1a), and the production method 1 except that the oxidizing agent is used at a ratio of 1.5 to 20 mol with respect to 1 mol of the present pyridazine compound (1dN). It can implement according to the method as described in.

［式中、記号は前記と同じ意味を表す。］
該反応は、本ピリダジン化合物（１ｄＮ）に代えて本ピリダジン化合物（１ｅＮ）を用い、製造法１３に記載の方法に準じて実施することができる。 Manufacturing method 14
The N oxide compound represented by the formula (N15) (hereinafter referred to as N oxide compound (N15)) is oxidized with the pyridazine compound represented by formula (1eN) (hereinafter referred to as present pyridazine compound (1eN)). It can manufacture by making an agent react.

[Wherein the symbols have the same meaning as described above. ]
This reaction can be carried out according to the method described in Production Method 13, using this pyridazine compound (1eN) instead of this pyridazine compound (1dN).

［式中、記号は前記と同じ意味を表す。］
はじめに、式（Ｍ３Ｎ）で示される化合物（以下、化合物（Ｍ３Ｎ）と記す。）を製造する方法について記載する。化合物（Ｍ３Ｎ）は、式（Ｍ３ｆ）で示される化合物（以下、化合物（Ｍ３ｆ）と記す。）と酸化剤とを反応させることにより製造することができる。
該反応は、本ピリダジン化合物（１ｄＮ）に代えて化合物（Ｍ３ｆ）を用いることにより、製造法１３に記載の方法に準じて実施することができる。
続いて、Ｎオキシド化合物（１−Ｎ）の製造する方法について記載する。Ｎオキシド化合物（１−Ｎ）は、化合物（Ｍ３Ｎ）と式（Ｒ３Ｎ）で示される化合物（以下、化合物（Ｒ３Ｎ）と記すとを塩基の存在下で反応させることにより製造することができる。
該反応は、化合物（Ｍ３）に代えて化合物（Ｍ３Ｎ）を用い、化合物（Ｒ３）に代えて化合物（Ｒ３Ｎ）を用いることにより、製造法４に記載の方法に準じて実施することができる。 Production method 15
The N oxide compound can be produced, for example, according to the following synthesis method.

[Wherein the symbols have the same meaning as described above. ]
First, a method for producing a compound represented by the formula (M3N) (hereinafter referred to as a compound (M3N)) will be described. Compound (M3N) can be produced by reacting a compound represented by the formula (M3f) (hereinafter referred to as compound (M3f)) with an oxidizing agent.
This reaction can be carried out according to the method described in Production Method 13 by using compound (M3f) in place of the present pyridazine compound (1dN).
Then, it describes about the manufacturing method of N oxide compound (1-N). The N oxide compound (1-N) can be produced by reacting the compound (M3N) with a compound represented by the formula (R3N) (hereinafter referred to as the compound (R3N)) in the presence of a base.
This reaction can be carried out according to the method described in Production Method 4, using compound (M3N) instead of compound (M3) and compound (R3N) instead of compound (R3).

  Next, specific examples of the pyridazine compound are shown below.

において、Ｒ²及びＲ³が水素原子であり、Ｒ¹、Ｒ⁴、ｎ、Ｒ⁵¹、Ｒ⁵²、及びＲ⁵³が［表１］〜［表１０］に記載の組み合わせである本ピリダジン化合物（以下、化合物群ＳＸ１と記す）。 Formula (1-1)

Wherein R ² and R ³ are hydrogen atoms, and R ¹ , R ⁴ , n, R ⁵¹ , R ⁵² , and R ⁵³ are the combinations described in [Table 1] to [Table 10] ( Hereinafter referred to as compound group SX1).

[Table 1]

[Table 2]

[Table 3]

[Table 4]

[Table 5]

[Table 6]

[Table 7]

[Table 8]

[Table 9]

[Table 10]

In Formula (1-1), R ² is a methyl group, R ³ is a hydrogen atom, and R ¹ , R ⁴ , n, R ⁵¹ , R ⁵² , and R ⁵³ are [Table 1] to [Table 10]. ] The pyridazine compound (hereinafter referred to as compound group SX2).
In Formula (1-1), R ² is a trifluoromethyl group, R ³ is a hydrogen atom, and R ¹ , R ⁴ , n, R ⁵¹ , R ⁵² , and R ⁵³ are [Table 1] to [ The pyridazine compounds (hereinafter referred to as compound group SX3), which are combinations described in Table 10].
In Formula (1-1), R ² is a chlorine atom, R ³ is a hydrogen atom, and R ¹ , R ⁴ , n, R ⁵¹ , R ⁵² , and R ⁵³ are [Table 1] to [Table 10]. The pyridazine compound (hereinafter referred to as compound group SX4).
In Formula (1-1), R ² is a fluorine atom, R ³ is a hydrogen atom, and R ¹ , R ⁴ , n, R ⁵¹ , R ⁵² , and R ⁵³ are [Table 1] to [Table 10]. The pyridazine compound (hereinafter referred to as compound group SX5).
In Formula (1-1), R ² is a hydrogen atom, R ³ is a methyl group, and R ¹ , R ⁴ , n, R ⁵¹ , R ⁵² , and R ⁵³ are [Table 1] to [Table 10]. ] The pyridazine compound (hereinafter referred to as compound group SX6).
In Formula (1-1), R ² is a chlorine atom, R ³ is a trifluoromethyl group, and R ¹ , R ⁴ , n, R ⁵¹ , R ⁵² , and R ⁵³ are represented by [Table 1] to [Table 1] The present pyridazine compounds (hereinafter referred to as compound group SX7), which are combinations described in Table 10].
In Formula (1-1), R ² is a hydrogen atom, R ³ is a chlorine atom, and R ¹ , R ⁴ , n, R ⁵¹ , R ⁵² , and R ⁵³ are [Table 1] to [Table 10]. The pyridazine compound (hereinafter referred to as compound group SX8).
In Formula (1-1), R ² is a hydrogen atom, R ³ is a fluorine atom, and R ¹ , R ⁴ , n, R ⁵¹ , R ⁵² , and R ⁵³ are [Table 1] to [Table 10]. The pyridazine compound (hereinafter referred to as compound group SX9).

において、Ｒ²及びＲ³が水素原子であり、Ｒ⁶が水素原子であり、Ｒ¹、Ｒ⁴、ｎ、Ｒ⁵¹、Ｒ⁵²、及びＲ⁵³が［表１］〜［表１０］に記載の組み合わせである本ピリダジン化合物（以下、化合物群ＳＸ１０と記す）。 Formula (1-2)

R ² and R ³ are hydrogen atoms, R ⁶ is a hydrogen atom, and R ¹ , R ⁴ , n, R ⁵¹ , R ⁵² , and R ⁵³ are described in [Table 1] to [Table 10]. This pyridazine compound (hereinafter referred to as compound group SX10).

In Formula (1-2), R ² is a methyl group, R ³ is a hydrogen atom, R ⁶ is a hydrogen atom, and R ¹ , R ⁴ , n, R ⁵¹ , R ⁵² , and R ⁵³ are This pyridazine compound (hereinafter referred to as compound group SX11) which is a combination described in [Table 1] to [Table 10].
In formula (1-1), R ² is a trifluoromethyl group, R ³ is a hydrogen atom, R ⁶ is a hydrogen atom, R ¹ , R ⁴ , n, R ⁵¹ , R ⁵² , and R ^The present pyridazine compounds in which ⁵³ is a combination described in [Table 1] to [Table 10] (hereinafter referred to as compound group SX12).
In Formula (1-2), R ² is a chlorine atom, R ³ is a hydrogen atom, R ⁶ is a hydrogen atom, and R ¹ , R ⁴ , n, R ⁵¹ , R ⁵² , and R ⁵³ are This pyridazine compound (hereinafter referred to as compound group SX13) which is a combination described in [Table 1] to [Table 10].
In Formula (1-2), R ² is a fluorine atom, R ³ is a hydrogen atom, R ⁶ is a hydrogen atom, and R ¹ , R ⁴ , n, R ⁵¹ , R ⁵² , and R ⁵³ are This pyridazine compound (hereinafter referred to as compound group SX14) which is a combination described in [Table 1] to [Table 10].
In Formula (1-2), R ² is a hydrogen atom, R ³ is a methyl group, R ⁶ is a hydrogen atom, and R ¹ , R ⁴ , n, R ⁵¹ , R ⁵² , and R ⁵³ are This pyridazine compound (hereinafter referred to as compound group SX15) which is a combination described in [Table 1] to [Table 10].
In the formula (1-2), R ² is a chlorine atom, R ³ is a trifluoromethyl group, R ⁶ is a hydrogen atom, R ¹ , R ⁴ , n, R ⁵¹ , R ⁵² , and R ^The present pyridazine compounds in which ⁵³ is a combination described in [Table 1] to [Table 10] (hereinafter referred to as compound group SX16).
In formula (1-2), R ² is a hydrogen atom, R ³ is a chlorine atom, R ⁶ is a hydrogen atom, and R ¹ , R ⁴ , n, R ⁵¹ , R ⁵² , and R ⁵³ are This pyridazine compound (hereinafter referred to as compound group SX17) which is a combination described in [Table 1] to [Table 10].
In Formula (1-2), R ² is a hydrogen atom, R ³ is a fluorine atom, R ⁶ is a hydrogen atom, and R ¹ , R ⁴ , n, R ⁵¹ , R ⁵² , and R ⁵³ are This pyridazine compound (hereinafter referred to as compound group SX18) which is a combination described in [Table 1] to [Table 10].

In Formula (1-2), R ² is a methyl group, R ³ is a hydrogen atom, R ⁶ is a fluorine atom, and R ¹ , R ⁴ , n, R ⁵¹ , R ⁵² , and R ⁵³ are This pyridazine compound (hereinafter referred to as compound group SX19) which is a combination described in [Table 1] to [Table 10].
In formula (1-1), R ² is a trifluoromethyl group, R ³ is a hydrogen atom, R ⁶ is a fluorine atom, R ¹ , R ⁴ , n, R ⁵¹ , R ⁵² , and R ^The present pyridazine compounds in which ⁵³ is a combination described in [Table 1] to [Table 10] (hereinafter referred to as compound group SX20).
In Formula (1-2), R ² is a chlorine atom, R ³ is a hydrogen atom, R ⁶ is a fluorine atom, and R ¹ , R ⁴ , n, R ⁵¹ , R ⁵² , and R ⁵³ are This pyridazine compound (hereinafter referred to as compound group SX21) which is a combination described in [Table 1] to [Table 10].
In Formula (1-2), R ² is a fluorine atom, R ³ is a hydrogen atom, R ⁶ is a fluorine atom, and R ¹ , R ⁴ , n, R ⁵¹ , R ⁵² , and R ⁵³ are This pyridazine compound (hereinafter referred to as compound group SX22) which is a combination described in [Table 1] to [Table 10].
In Formula (1-2), R ² is a hydrogen atom, R ³ is a methyl group, R ⁶ is a fluorine atom, and R ¹ , R ⁴ , n, R ⁵¹ , R ⁵² , and R ⁵³ are This pyridazine compound (hereinafter referred to as compound group SX23) which is a combination described in [Table 1] to [Table 10].
In Formula (1-2), R ² is a chlorine atom, R ³ is a trifluoromethyl group, R ⁶ is a fluorine atom, R ¹ , R ⁴ , n, R ⁵¹ , R ⁵² , and R ^The present pyridazine compound ⁵³ is a combination described in [Table 1] to [Table 10] (hereinafter referred to as compound group SX24).
In the formula (1-2), R ² is a hydrogen atom, R ³ is a chlorine atom, R ⁶ is a fluorine atom, and R ¹ , R ⁴ , n, R ⁵¹ , R ⁵² , and R ⁵³ are This pyridazine compound (hereinafter referred to as compound group SX25) which is a combination described in [Table 1] to [Table 10].
In Formula (1-2), R ² is a hydrogen atom, R ³ is a fluorine atom, R ⁶ is a fluorine atom, and R ¹ , R ⁴ , n, R ⁵¹ , R ⁵² , and R ⁵³ are This pyridazine compound (hereinafter referred to as compound group SX26), which is a combination described in [Table 1] to [Table 10].

  Next, specific examples of the N oxide compound are shown below.

において、Ｒ^2N及びＲ^3Nが水素原子であり、Ｒ^1N、Ｒ^4N、Ｒ^51N、Ｒ^52N、及びＲ^53Nが［表１１］〜［表１６］に記載の組み合わせである化合物（以下、化合物群ＳＸ２７と記す）。 Formula (1-N11)

In, R ^2N and R ^3N are hydrogen ^{atoms, R 1N, R 4N, R} 51N, R 52N, and R ^53N is Table 11] to compound a combination according to Table 16] (hereinafter, compound group SX27).

[Table 11]

[Table 12]

[Table 13]

[Table 14]

[Table 15]

[Table 16]

In the formula (1-N11), R ^2N is a methyl group, R ^3N represents a hydrogen ^{atom, R 1N, R 4N, R} 51N, R 52N, and R ^53N are in Table 11] to [Table 16] The compound which is a combination of the description (hereinafter referred to as compound group SX28).
In the formula (1-N11), R ^2N is trifluoromethyl group, R ^3N represents a hydrogen ^{atom, R 1N, R 4N, R} 51N, R 52N, and R ^53N is Table 11] to [Table 16 ] The compound which is a combination of description (henceforth a compound group SX29).
In the formula (1-N11), R ^2N is a chlorine atom, R ^3N represents a hydrogen ^{atom, R 1N, R 4N, R} 51N, R 52N, and R ^53N are in Table 11] to [Table 16] The compound which is a combination of the description (hereinafter referred to as compound group SX30).
In the formula (1-N11), R ^2N is a fluorine atom, R ^3N represents a hydrogen ^{atom, R 1N, R 4N, R} 51N, R 52N, and R ^53N are in Table 11] to [Table 16] The compound which is a description combination (hereinafter, referred to as a compound group SX31).
In the formula (1-N11), R ^2N represents a hydrogen atom, R ^3N is a methyl ^{group, R 1N, R 4N, R} 51N, R 52N, and R ^53N are in Table 11] to [Table 16] A compound which is a combination of the descriptions (hereinafter referred to as compound group SX32).
In the formula (1-N11), R ^2N is a chlorine atom, R ^3N is trifluoromethyl ^{group, R 1N, R 4N, R} 51N, R 52N, and R ^53N is Table 11] to [Table 16 ] The compound which is a combination of description (henceforth the compound group SX33).
In the formula (1-N11), R ^2N represents a hydrogen atom, R ^3N is a chlorine ^{atom, R 1N, R 4N, R} 51N, R 52N, and R ^53N are in Table 11] to [Table 16] The compound which is a combination of the description (hereinafter referred to as compound group SX34).
In the formula (1-N11), R ^2N represents a hydrogen atom, R ^3N is a fluorine ^{atom, R 1N, R 4N, R} 51N, R 52N, and R ^53N are in Table 11] to [Table 16] The compound which is a combination of the description (hereinafter referred to as compound group SX35).

において、Ｒ^2N及びＲ^3Nが水素原子であり、Ｒ^1N、Ｒ^4N、Ｒ^51N、Ｒ^52N、及びＲ^53Nが［表１１］〜［表１６］に記載の組み合わせである化合物（以下、化合物群ＳＸ３６と記す）。 Formula (1-N12)

In, R ^2N and R ^3N are hydrogen ^{atoms, R 1N, R 4N, R} 51N, R 52N, and R ^53N is Table 11] to compound a combination according to Table 16] (hereinafter, compound group SX36).

In the formula (1-N12), R ^2N is a methyl group, R ^3N represents a hydrogen ^{atom, R 1N, R 4N, R} 51N, R 52N, and R ^53N are in Table 11] to [Table 16] A compound which is a combination of the descriptions (hereinafter referred to as compound group SX37).
In the formula (1-N12), R ^2N is trifluoromethyl group, R ^3N represents a hydrogen ^{atom, R 1N, R 4N, R} 51N, R 52N, and R ^53N is Table 11] to [Table 16 ] Is a combination (hereinafter referred to as compound group SX38).
In the formula (1-N12), R ^2N is a chlorine atom, R ^3N represents a hydrogen ^{atom, R 1N, R 4N, R} 51N, R 52N, and R ^53N are in Table 11] to [Table 16] The compound which is a combination of the description (hereinafter referred to as compound group SX39).
In the formula (1-N12), R ^2N is a fluorine atom, R ^3N represents a hydrogen ^{atom, R 1N, R 4N, R} 51N, R 52N, and R ^53N are in Table 11] to [Table 16] The compound which is a description combination (hereinafter, referred to as a compound group SX40).
In the formula (1-N12), R ^2N represents a hydrogen atom, R ^3N is a methyl ^{group, R 1N, R 4N, R} 51N, R 52N, and R ^53N are in Table 11] to [Table 16] A compound which is a combination of the descriptions (hereinafter referred to as compound group SX41).
In the formula (1-N12), R ^2N is a chlorine atom, R ^3N is trifluoromethyl ^{group, R 1N, R 4N, R} 51N, R 52N, and R ^53N is Table 11] to [Table 16 ] The compound which is a combination of description (henceforth compound group SX42).
In the formula (1-N12), R ^2N represents a hydrogen atom, R ^3N is a chlorine ^{atom, R 1N, R 4N, R} 51N, R 52N, and R ^53N are in Table 11] to [Table 16] The compound which is a combination of the description (hereinafter referred to as compound group SX43).
In the formula (1-N12), R ^2N represents a hydrogen atom, R ^3N is a fluorine ^{atom, R 1N, R 4N, R} 51N, R 52N, and R ^53N are in Table 11] to [Table 16] The compound which is a combination of the description (hereinafter referred to as compound group SX44).

において、Ｒ^2N及びＲ^3Nが水素原子であり、Ｒ^6Nが水素原子であり、Ｒ^1N、Ｒ^4N、Ｒ^51N、Ｒ^52N、及びＲ^53Nが［表１１］〜［表１６］に記載の組み合わせである化合物（以下、化合物群ＳＸ４５と記す）。 Formula (1-N13)

In a R ^2N and R ^3N are hydrogen atom, R ^6N are hydrogen atoms, R ^1N, R ^4N, the combination according to R ^51N, R ^52N, and R ^53N is Table 11] to [Table 16] (Hereinafter referred to as compound group SX45).

In the formula (1-N13), R ^2N is a methyl group, R ^3N represents a hydrogen atom, an R ^6N are hydrogen ^{atoms, R 1N, R 4N, R} 51N, R 52N, and R ^53N is Table 11] to [Table 16] are compounds (hereinafter referred to as compound group SX46).
In the formula (1-N13), R ^2N is trifluoromethyl, R ^3N represents a hydrogen atom, an R ^6N are hydrogen ^{atoms, R 1N, R 4N, R} 51N, R 52N, and R ^53N is The compound which is a combination as described in [Table 11]-[Table 16] (henceforth compound group SX47).
In the formula (1-N13), R ^2N is a chlorine atom, R ^3N represents a hydrogen atom, an R ^6N are hydrogen ^{atoms, R 1N, R 4N, R} 51N, R 52N, and R ^53N is Table 11] to [Table 16] are compounds (hereinafter referred to as compound group SX48).
In the formula (1-N13), R ^2N is a fluorine atom, R ^3N represents a hydrogen atom, an R ^6N are hydrogen ^{atoms, R 1N, R 4N, 51N} , R 52N, and R ^53N is Table 11 ] To a compound described in [Table 16] (hereinafter referred to as compound group SX49).
In the formula (1-N13), R ^2N represents a hydrogen atom, R ^3N represents a methyl group, an R ^6N are hydrogen ^{atoms, R 1N, R 4N, R} 51N, R 52N, and R ^53N is Table 11] to [Table 16] are compounds (hereinafter, referred to as compound group SX50).
In the formula (1-N13), R ^2N is a chlorine atom, R ^3N is trifluoromethyl group, a R ^6N are hydrogen ^{atoms, R 1N, R 4N, R} 51N, R 52N, and R ^53N is The compound which is a combination as described in [Table 11]-[Table 16] (henceforth a compound group SX51).
In the formula (1-N13), R ^2N represents a hydrogen atom, R ^3N is a chlorine atom, a R ^6N are hydrogen ^{atoms, R 1N, R 4N, R} 51N, R 52N, and R ^53N is Table 11] to [Table 16] are compounds (hereinafter referred to as compound group SX52).
In the formula (1-N13), R ^2N represents a hydrogen atom, R ^3N is a fluorine atom, a R ^6N are hydrogen ^{atoms, R 1N, R 4N, R} 51N, R 52N, and R ^53N is Table 11] to [Table 16] are compounds (hereinafter referred to as compound group SX53).

In the formula (1-N13), R ^2N is a methyl group, R ^3N represents a hydrogen atom, an R ^6N is fluorine ^{atom, R 1N, R 4N, R} 51N, R 52N, and R ^53N is Table 11] to [Table 16] are compounds (hereinafter referred to as compound group SX54).
In the formula (1-N13), R ^2N is trifluoromethyl group, R ^3N represents a hydrogen atom, an R ^6N is fluorine ^{atom, R 1N, R 4N, R} 51N, R 52N, and R ^53N is The compound which is a combination as described in [Table 11]-[Table 16] (henceforth a compound group SX55).
In the formula (1-N13), R ^2N is a chlorine atom, R ^3N represents a hydrogen atom, an R ^6N is fluorine ^{atom, R 1N, R 4N, R} 51N, R 52N, and R ^53N is Table 11] to [Table 16] are compounds (hereinafter referred to as compound group SX56).
In the formula (1-N13), R ^2N is a fluorine atom, R ^3N represents a hydrogen atom, an R ^6N is fluorine ^{atom, R 1N, R 4N, R} 51N, R 52N, and R ^53N is Table 11] to [Table 16] are compounds (hereinafter referred to as compound group SX57).
In the formula (1-N13), R ^2N represents a hydrogen atom, R ^3N represents a methyl group, an R ^6N is fluorine ^{atom, R 1N, R 4N, R} 51N, R 52N, and R ^53N is Table 11] to [Table 16] are compounds (hereinafter referred to as compound group SX58).
In the formula (1-N13), R ^2N is a chlorine atom, R ^3N is trifluoromethyl group, a R ^6N is fluorine ^{atom, R 1N, R 4N, R} 51N, R 52N, and R ^53N is The compound which is a combination as described in [Table 11]-[Table 16] (henceforth a compound group SX59).
In the formula (1-N13), R ^2N represents a hydrogen atom, R ^3N is a chlorine atom, a R ^6N is fluorine ^{atom, R 1N, R 4N, R} 51N, R 52N, and R ^53N is Table 11] to [Table 16] are compounds (hereinafter referred to as compound group SX60).
In the formula (1-N13), R ^2N represents a hydrogen atom, R ^3N is a fluorine atom, a R ^6N is fluorine ^{atom, R 1N, R 4N, n} , R 51N, R 52N, and R ^53N is The compound which is a combination as described in [Table 1]-[Table 10] (henceforth a compound group SX61).

からなる、ニコチン性アセチルコリン受容体競合的モジュレーターの群。
亜群ａ−２：
アクリナトリン（acrinathrin）、アレスリン（allethrin）、ビフェントリン（bifenthrin）、カッパビフェントリン（kappa-bifenthrin）、ビオアレスリン（bioallethrin）、ビオレスメトリン（bioresmethrin）、シクロプロトリン（cycloprothrin）、シフルトリン（cyfluthrin）、ベータ−シフルトリン（beta-cyfluthrin）、シハロトリン（cyhalothrin）、ガンマシハロトリン（gamma-cyhalothrin）、ラムダシハロトリン（lambda-cyhalothrin）、シペルメトリン（cypermethrin）、アルファシペルメトリン（alpha-cypermethrin）、べータシペルメトリン（beta-cypermethrin）、シータシペルメトリン（theta-cypermethrin）、ゼータシペルメトリン（zeta-cypermethrin）、シグマシペルメトリン（sigma-cypermethrin）、シフェノトリン（cyphenothrin）、デルタメトリン（deltamethrin）、エンペントリン（empenthrin）、エスフェンバレレート（esfenvalerate）、エトフェンプロックス（etofenprox）、フェンプロパトリン（fenpropathrin）、フェンバレレート（fenvalerate）、フルシトリネート（flucythrinate）、フルメトリン（flumethrin）、フルバリネート（fluvalinate）、タウフルバリネート（tau-fluvalinate）、ハルフェンプロックス（halfenprox）、ヘプタフルトリン（heptafluthrin）、イミプロトリン（imiprothrin）、カデスリン（kadethrin）、メペルフルトリン（meperfluthrin）、モンフルオロトリン（momfluorothrin）、ペルメトリン（permethrin）、フェノトリン（phenothrin）、プラレトリン（prallethrin）、ピレトリン（pyrethrins）、レスメトリン（resmethrin）、シラフルオフェン（silafluofen）、テフルトリン（tefluthrin）、カッパテフルトリン（kappa-tefluthrin）、テトラメトリン（tetramethrin）、テトラメチルフルトリン（tetramethylfluthrin）、トラロメトリン（tralomethrin）、トランスフルトリン（transfluthrin）、ベンフルトリン（benfluthrin）、フルフェンプロックス（flufenoprox）、フルメスリン（flumethrin）、フラメトリン（furamethrin）、メトフルトリン（metofluthrin）、プロフルトリン（profluthrin）及びジメフルトリン（dimefluthrin）からなる、ナトリウムチャネルモジュレーターの群。
亜群ａ−３：
エチプロール（ethiprole）、フィプロニル（fipronil）及びフルフィプロール（flufiprole）からなるGABA作動性塩素イオンチャネルブロッカー、並びに、アフォクソラネル（afoxalaner）、フルララネル（fluralaner）、ブロフラニリド（broflanilide）及びフルキサメタミド（fluxametamide）からなるGABA作動性塩素イオンチャネルアロステリックモジュレーターの群。
亜群ａ−４：
クロラントラニリプロール（chlorantraniliprole）、シアントラニルプロール（cyantraniliprole）、シクラニリプロール（cycloniliprole）、フルベンジアミド（flubendiamide）、テトラニリプロール（tetraniliprole）及びシハロジアミド（cyhalodiamide）からなる、リアノジン受容体モジュレーターの群。
亜群ａ−５：
アラニカルブ（alanycarb）、アルジカルブ（aldicarb）、ベンダイオカルブ（bendiocarb）、ベンフラカルブ（benfuracarb）、ブトカルボキシム（butocarboxim）、ブトキシカルボキシム（butoxycarboxim）、カルバリル（carbaryl：NAC）、カルボフラン（carbofuran）、カルボスルファン（carbosulfan）、エチオフェンカルブ（ethiofencarb）、フェノブカルブ（fenobucarb：BPMC）、ホルメタネート（formetanate）、フラチオカルブ（furathiocarb）、イソプロカルブ（isoprocarb：MIPC）、メチオカルブ（methiocarb）、メソミル（methomyl）、メトルカルブ（metolcarb：MTMC）、オキサミル（oxamyl）、ピリミカーブ（pirimicarb）、プロポキスル（propoxur：PHC）、チオジカルブ（thiodicarb）、チオファノックス（thiofanox）、トリアザメート（triazamate）、トリメタカルブ（trimethacarb）、XMC及びキシリルカルブ（xylylcarb：MPMC）からなる、カーバメート系のアセチルコリンエステラーゼ（AChE）阻害剤の群。
亜群ａ−６：
アバメクチン（abamectin）、フルエンスルホン（fluensulfone）、チオキサザフェン（tioxazafen）、及びフルアザインドリジン（fluazaindolizine）からなる、殺線虫活性化合物の群。
亜群ａ−７：
菌根菌（Mycorrhiza Fungi）、アルスロボトリス・ダクチロイデス（Arthrobotrys dactyloides）、バチルス・チューリンゲンシス（Bacillus thuringiensis）、バチルス・フィルムス（Bacillus firmus）、バチルス・メガテリウム（Bacillus megaterium）、バチルス・アミロリケファシエンス（Bacillus amyloliquefaciens）、ヒルステラ・ロッシリエンシス（Hirsutella rhossiliensis）、ヒルステラ・ミネソテンシス（Hirsutella minnesotensis）、モナクロスポリウム・フィマトパガム（Monacrosporium phymatopagus）、パスツーリア・ニシザワエ（Pasteuria nishizawae）、パスツーリア・ペネトランス（Pasteuria penetrans）、パスツーリア・ウスガエ（Pasteuria usgae）、バーティシリウム・クラミドスポリウム（Verticillium chlamydosporium）及びハーピンタンパク（Harpin protein）からなる、微生物資材の群。 Examples of the compound of group (a) include compounds of subgroups a-1, a-2, a-3, a-4, a-5, a-6 and a-7.
Subgroup a-1:
Acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, flupyrifurone, flupyradifurone ), Dichloromesothiaz (dicloromezotiaz) and a compound represented by the following formula (CAS registration number 1689566-03-7)

A group of competitive modulators of nicotinic acetylcholine receptors.
Subgroup a-2:
Acrinathrin, allethrin, bifenthrin, kappa-bifenthrin, bioallethrin, bioresmethrin, cycloprothrin, cyfluthrin, beta beta-cyfluthrin), cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, cypermethrin, alpha-cypermethrin, betacypermethrin ( beta-cypermethrin), theta-cypermethrin, theta-cypermethrin, sigma-cypermethrin, cyphenothrin, deltamethrin, empenthrin, esf Enfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, fluvalinate, tau-fluvalinate ), Halfenprox, heptafluthrin, imiprothrin, kadethrin, meperfluthrin, momfluorothrin, permethrin, phenothrin, praothrin prallethrin), pyrethrin (pyrethrins), resmethrin (resmethrin), silafluofen (silafluofen), tefluthrin (tefluthrin), kappa-tefluthrin, tetramethrin (tetramethrin), tetramethi Flutrin (tetramethylfluthrin), tralomethrin (tralomethrin), transfluthrin (transfluthrin), benfluthrin (benfluthrin), flufenprox (flufenoprox), flumerin (flumethrin), framethrin (furamethrin), methfluthrin (metofluthrin), profluthrin and profluthrin (profluthrin) A group of sodium channel modulators consisting of (dimefluthrin).
Subgroup a-3:
GABAergic chloride channel blocker consisting of ethiprole, fipronil and flufiprole, and GABA consisting of afoxalaner, fluralaner, broflanilide and fluxametamide A group of agonistic chloride channel allosteric modulators.
Subgroup a-4:
Group of ryanodine receptor modulators consisting of chlorantraniliprole, cyantraniliprole, cyclaniliprole, flubendiamide, tetraniliprole and cyhalodiamide .
Subgroup a-5:
Alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl (NAC), carbofuran, carbofuran Fan (carbosulfan), ethiofencarb (fthiobucarb), fenobucarb (BPMC), formethanate (formetanate), furathiocarb (furathiocarb), isoprocarb (isoprocarb: MIPC), methiocarb (methiocarb), methomyl (methomyl), metolcarb (MTMC) , Oxamyl, pirimicarb, propoxur (PHC), thiodicarb, thiofanox, triazamate, trimethacarb, XMC and xylica Bed (xylylcarb: MPMC) consists, the group of carbamates acetylcholinesterase (AChE) inhibitors.
Subgroup a-6:
A group of nematicidal active compounds consisting of abamectin, fluensulfone, tioxazafen, and fluazaindolizine.
Subgroup a-7:
Mycorrhiza Fungi, Arthrobotrys dactyloides, Bacillus thuringiensis, Bacillus firmus, Bacillus megaterium, Bacillus amyloliquefaciens (Bacillus amyloliquefaciens), Hirsutella rhossiliensis, Hirsutella minnesotensis, Monacrosporium phymatopagus, Pasturiatransurie, Pasturiapass A group of microbial materials consisting of Pasteuria usgae, Verticillium chlamydosporium and Harpin protein.

As used in the present invention, acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, fluradifurone, fluradifurone , Triflumezopyrim, acrinathrin, allethrin, bifenthrin, kappa-bifenthrin, bioallethrin, bioresmethrin, cycloresin, prothrin (Cyfluthrin), beta-cyfluthrin, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, Permethrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, sigma-cypermethrin , Cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate , Flumethrin, fluvalinate, tau-fluvalinate, halfenprox, heptafluthrin, imiprothrin, kadethrin, meperf Luthrin (meperfluthrin), monfluorothrin (momfluorothrin), permethrin (phenmethrin), praothrin (prallethrin), pyrethrin (pyrethrins), resmethrin (resmethrin), silafluofen, tefluthrin (tefluthrin) (Kappa-tefluthrin), tetramethrin, tetramethylfluthrin, tralomethrin, transfluthrin, benfluthrin, flufenprox, flumethrin, flamethrin furamethrin), methofluthrin, profluthrin, dimefluthrin, ethiprole, fipronil, furfiprole, Lorantraniliprole, cyantraniliprole, cycloniliprole, flubendiamide, cyhalodiamide, alaniccarb, aldicarb, bendiocarb , Benfuracarb, butocarboxim, butoxycarboxim, carbaryl (NAC), carbofuran, carbosulfan, ethiofencarb, fenobucarb (BPMC) , Formetanate, furathiocarb, isoprocarb (MIPC), methiocarb, metomyl, metolcarb (MTMC), oxamyl, Pirimicarb, propoxur (PHC), thiodicarb, thiofanox, triazamate, trimethacarb, XMC, xylylcarb (MPMC), abamectin and fluenesulfone (Fluensulfone) is a known compound, for example, “MeisterPro Crop Protection Handbook Vol. 100 (2014) "or the like.
These compounds can be obtained from commercially available preparations or produced by known methods.
Dichloromesothiaz (CAS registration number: 1263629-39-5), tetraniliprolol (CAS registration number: 1229654-66-3), floxamethamide (CAS registration number: 928783-29-3), used in the present invention, Afoxolanel (CAS registration number: 1093861-60-9), fluralanel (CAS registration number: 864731-61-3), brofuranilide (CAS registration number: 1207727-04-5), fluazaindolizine (CAS registration number: 1254304- 22-7), Thioxazaphen (CAS registration number: 330459-31-9) and insecticidal compound α (CAS registration number: 1689566-03-7) are all known compounds, for example, International Publication No. 2011/017342 No., International Publication No. 2010/066952, International Publication No. 2007/026965, International Publication No. 2007/079962, International Publication No. 2005/0885216, International Publication No. 2010 No. 018714, WO 2010/129500, WO 2006/114400, and can be produced respectively by the method described in WO 2012/029672.
Mycorrhiza Fungi, Arthrobotrys dactyloides, Bacillus thuringiensis, Bacillus firmus, Bacillus megaterium used in the present invention, Bacillus amyloliquefaciens, Hirsutella rhossiliensis, Hirsutella minnesotensis, Monacrosporium phymatopagus, Monacrosporium phymatopagus, Pasteuria e (Pasteuria penetrans), Pasturia usgae, Verticillium chlamydosporium and Harpin protein are all public A microbial materials, obtained from commercially available preparations or obtained by production using a known method.

As the compound of the group (b), the following compounds of subgroups b-1, b-2, b-3, b-4, b-5, b-6, b-7, b-8 and b-9 Is mentioned.
Subgroup b-1:
Azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, dinicoazole, diniconazole-M, epiconconazole, ethaconazole (Etaconazole), fenarimol, fenbuconazole, fluquinconazole, quinconazole, flusilazole, flutriafol, hexaconazole, imazaril ( imazalil), imibenconazole, ipconazole, metconazole, microbutanil, nuarimol, oxpoconazole, o Spoconazole fumarate, pefurazoate, penconazole, prochloraz, propiconazole, prothioconazole, pyrifenox, pyrisoxazole ), Simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triflumizole, triforine and triticonazole A group of sterol biosynthesis inhibitors.
Subgroup b-2:
Azoxystrobin, coumoxystrobin, dimoxystrobin, enoxastrobin, famoxadone, fenamidone, fenaminstrobin, full Phenoxystrobin, fluoxastrobin, cresoxim-methyl, mandestrobin, metinominostrobin, orysastrobin, picoxystrobin , Pyraclostrobin, pyrametostrobin, pyraoxystrobin, trifloxystrobin, pyribencarb, triclopyricarb, triazopyricarb Consisting de (cyazofamid) and amisulbrom (amisulbrom), the group of Qo inhibitors (Quinone outside inhibitors).
Subgroup b-3:
A group of RNA polymerase I inhibitors consisting of benalaxyl, benalaxyl-M, furalaxyl, metalaxyl, metalaxyl-M, oxadixyl and ofurace .
Subgroup b-4:
Benodanil, benzovindiflupyr, bixafen, boscalid, carboxin, fenfuram, fluopyram, flutolanil, fluxapyroxad ), Furametpyr, isofetamid, isoprazam, mepronil, oxycarboxin, penthiopyrad, penflufen, sedaxane, thifluzamide, thifluamide (Pyraziflumid), pidiflumetofen (CAS registration number 1228284-64-7), 3-difluoromethyl-1-methyl-N- (1,1,3-trimethylindan-4-yl) pyrazole-4- Carboxamide (CAS registration No. 141573-94-6), 3-difluoromethyl-1-methyl-N-[(3R) -1,1,3-trimethylindan-4-yl] pyrazole-4-carboxamide (CAS Registry Number 1352994-67-) 2), 3-difluoromethyl-N- (7-fluoro-1,1,3-trimethylindan-4-yl) -1-methylpyrazole-4-carboxamide (CAS registration number 1383809-87-7), 3- Difluoromethyl-N-[(3R) -7-fluoro-1,1,3-trimethylindan-4-yl] -1-methylpyrazole-4-carboxamide (CAS Registry Number 1513466-73-3) and N-cyclo Propyl-3- (difluoromethyl) -5-fluoro-N- (5-chloro-2-isopropylbenzyl) -1-methyl-1H-pyrazole-4-carboxamide (CAS Registry Number 1255734-28-1) Ranaru, the group of succinate dehydrogenase inhibitors.
Subgroup b-5:
It consists of benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate, thiophanate-methyl, diethofencarb, zoxamide and ethaboxam. A group of β-tubulin polymerization inhibitors.
Subgroup b-6:
Ferbam, mancozeb, manneb, maneb, metiram, propineb, thiram, zineb, ziram, captan, captafol ), Folpet, chlorothalonil, tolylfluanid, guazatine, iminoctadine, anilazine, dithianon, chinomethionate or quinomethionate fluoride A group of multi-acting point contact active compounds consisting of
Subgroup b-7:
Dimethomorph, flumorph, pyrimorph, benthiavalicarb, benthivalicarb-isopropyl, iprovalicarb, valifenalate and mandipropamid A group of cellulose synthesis inhibitors.
Subgroup b-8:
MAP (mitogen-activated protein) / histidine kinase inhibitor in osmotic signal transduction consisting of fenpiclonil, fludioxonil, clozolinate, iprodione, procymidone and vinclozolin group.
Subgroup b-9:
A group of other fungicides consisting of tolclofos-methyl, oxathiapiproline, picarbutrazox, fluopicolide and silthiofam.

Azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, diniconazole M, diniconazole-M, epoxico, used in the present invention Epoxiconazole, etaconazole, fenarimol, fenbuconazole, fluquinconazole, quinconazole, flusilazole, flutriafol, hexaconazole (Hexaconazole), imazalil, imibenconazole, ipconazole, metconazole, microbutanil, nuarimol, oxpoconazo Oxpoconazole, oxpoconazole fumarate, pefurazoate, penconazole, prochloraz, propiconazole, prothioconazole, pyrifenox ( pyrifenox, pyrisoxazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triflumizole, triforine, triforine Ticononazole, azoxystrobin, coumoxystrobin, dimoxystrobin, enoxastrobin, famoxadone, fenamidone (fe namidone, phenaminestrobin, flufenoxystrobin, fluoxastrobin, kresoxim-methyl, mandestrobin, metinominostrobin, oryastrobine (Orysastrobin), picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, trifloxystrobin, pyribencarb, triclopyricarb (Triclopyricarb), cyazofamid (cyazofamid), amisulbrom (benisaxyl), benalaxyl M (benalaxyl-M), furalaxyl (furalaxyl), metalaxyl (metalaxyl), metalaxyl M (metalaxyl-M), oxadi Oxadixyl, ofurace, benodanil, benzovindiflupyr, bixafen, boscalid, carboxin, fenfuram, fluopyram, flutolanil (Flutolanil), fluxapyroxad, furametpyr, isofetamid, isopyrazam, mepronil, oxycarboxin, penthiopyrad, penflufen, penflufen, penflufen (Sedaxane), thifluzamide, benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate, thiophanate-methyl, Etofencarb, diexofencarb, zoxamide, ethaboxam, ferbam, mancozeb, maneb, maneb, metiram, propineb, thiram, zineb ), Ziram, captan, captafol, folpet, chlorothalonil, tolylfluanid, guazatine, iminoctadine, anilazine , Dithianon, chinomethionat or quinomethionate, fluoroimide, dimethomorph, flumorph, pyrimorph, benchthiavalicarb, benchthiavalicarb-isopropyl ), Iprovalicarb, valifenalate, mandipropamid, fenpiclonil, fludioxonil, clozolinate, iprodione, procymidone, vincrozoline, vinclozoline, vinclozoline Tolclofos-methyl, oxathiapiproline, picarbutrazox, fluopicolide, and silthiofam are all “MeisterPro Crop Protection Handbook Vol. 100 (2014) "and the like. These compounds can be obtained from commercially available preparations or produced by known methods.
3-Difluoromethyl-1-methyl-N- (1,1,3-trimethylindan-4-yl) pyrazole-4-carboxamide (CAS registration number 141573-94-6), 3-difluoro used in the present invention Methyl-1-methyl-N-[(3R) -1,1,3-trimethylindan-4-yl] pyrazole-4-carboxamide (CAS registration number 1352994-67-2) is a known compound, For example, it can be produced by the method described in International Publication No. 2011/162397, respectively.
Pyraziflumid used in the present invention is a known compound and can be produced, for example, by the method described in International Publication No. 2007/072999.
Pidiflumetofen used in the present invention is a known compound and can be produced, for example, by the method described in WO2010 / 063700.
3-Difluoromethyl-N- (7-fluoro-1,1,3-trimethylindan-4-yl) -1-methylpyrazole-4-carboxamide (CAS registration number 1383809-87-7) used in the present invention 3-difluoromethyl-N-[(3R) -7-fluoro-1,1,3-trimethylindan-4-yl] -1-methylpyrazole-4-carboxamide (CAS Registry Number 1513466-73-3) is All are known compounds and can be produced, for example, by the methods described in International Publication No. 2012/084812.
N-cyclopropyl-3- (difluoromethyl) -5-fluoro-N- (5-chloro-2-isopropylbenzyl) -1-methyl-1H-pyrazole-4-carboxamide (CAS registration number) used in the present invention 1255734-28-1) is a known compound and can be produced, for example, by the method described in International Publication No. 2013/160387.

Below, the example of the combination of this pyridazine compound and this compound in this invention composition is described. The abbreviation for SX means “any one pyridazine compound selected from compound groups SX1 to SX61”.
Acetamiprid + SX, clothianidin + SX, dinotefuran + SX, imidacloprid + SX, nitenpyram + SX, thiacloprid + SX, thiamethoxam + SX, flupiradiflon + SX, sulfoxafurol + SX, triflumezopyrim + SX, dichloromesothiaz compound + SX
Acrinatrin + SX, Aresulin + SX, Bifenthrin + SX, Kappa Bifenthrin + SX, Bioaresulin + SX, Bioresmethrin + SX, Cycloproton + SX, Cyfluthrin + SX, Beta-Cyfluthrin + SX, Cyhalothrin + SX, Gamma Cyhalothrin X SX, Gamma Cyhalothrin X SX + SX, alphacypermethrin + SX, betacypermethrin + SX, thetacypermethrin + SX, zetacypermethrin + SX, sigmacipermethrin + SX, ciphenothrin + SX, deltamethrin + SX, empentrin + SX, esfenvalerate + SX, ethofenprofenprox Thrin + SX, fenvalerate + SX, flucitrinate + SX, flumethrin + SX, fluva Nate + SX, Taufulvalinate + SX, Halfenprox + SX, Heptafluthrin + SX, Imiprothrin + SX, Kadeslin + SX, Meperfluthrin + SX, Monfluorotrin + SX, Permethrin + SX, Phetothrin + SX, Praretrin + SX, Pyrethrin + SX, Pyrethrin + SX Tefluthrin + SX, kappatefluthrin + SX, tetramethrin + SX, tetramethylfurthrin + SX, tralomethrin + SX, transfluthrin + SX, benfurthrin + SX, flufenprox + SX, flumethrin + SX, flamethrin + SX, methfluthrin + SX, proflutriline + SX
Etiprol + SX, fipronil + SX, flupiprol + SX, afoxolanel + SX, fluralanel + SX, brofuranilide + SX, floxamethamide + SX,
Chlorantraniliprole + SX, cyantranylprolol + SX, cyclaniliprol + SX, fulvendiamide + SX, tetraniprolol + SX, cyhalodiamide + SX,
Aranicarb + SX, Aldicarb + SX, Bendiocarb + SX, Benfuracarb + SX, Butcarboxyme + SX, Butoxycarboxyme + SX, Carbaryl + SX, Carbofuran + SX, Carbosulfan + SX, Ethiophene carb + SX, Fenthiocarb + SX, Formethanate + carb, SX Methiocarb + SX, Mesomil + SX, Metorcarb + SX, Oxamyl + SX, Pirimicurve + SX, Propoxyl + SX, Thiodicarb + SX, Thiophanox + SX, Triazamate + SX, Trimetacarb + SX, XMC + SX, Xylylcarb + SX,
Abamectin + SX, fluenesulfone + SX, thioxazaphen + SX, fluazaindolizine + SX,
Mycorrhizal fungi + SX, Arthrobotris dactylides + SX, Bacillus thuringiensis + SX, Bacillus films + SX, Bacillus megaterium + SX, Bacillus amyloliquefaciens + SX, Hilstera rossiliensis + SX, Hilstera minneso Crospodium fimatopagum + SX, Pasteuria nisawae + SX, Pasteuria penetrans + SX, Pasteuria usgae + SX, Verticillium kuramidosporia + SX, Harpin protein + SX,

Azaconazole + SX, Viteltanol + SX, Bromuconazole + SX, Cyproconazole + SX, Difenoconazole + SX, Diniconazole + SX, Diniconazole M + SX, Epoxyconazole + SX, Etaconazole + SX, Fenarimol + SX, Fenbuconazole + SX, Flubuconazole X Flusilazole + SX, flutriazole + SX, hexaconazole + SX, imazalil + SX, imibenconazole + SX, ipconazole + SX, metconazole + SX, microbutanyl + SX, nuarimol + SX, oxpoconazole + SX, oxpoconazole fumarate + SX, pefrazoate + SX , Penconazole + SX, prochloraz + SX, propiconazole + SX, prothiocona Zole + SX, Pyrifenox + SX, Pyrioxazole + SX, Cimeconazole + SX, Tebuconazole + SX, Tetraconazole + SX, Triadimephone + SX, Triadimenol + SX, Triflumizole + SX, Triphorine + SX, Triticonazole + SX,
Azoxystrobin + SX, umoxistrobin + SX, dimoxystrobin + SX, enoxastrobin + SX, famoxadone + SX, phenamidon + SX, phenaminestrobin + SX, fluphenoxystrobin + SX, fluoxastrobin + SX, cresoxime-methyl + SX, Mandestrobin + SX, Metominostrobin + SX, Orissatrobin + SX, Picoxystrobin + SX, Pyraclostrobin + SX, Pyrametostrobin + SX, Pyroxystrobin + SX, Pyribencarb + SX, Triclopyricarb + SX, Cyazofamid + SX, Amisulbrom + SX ,
Benalaxyl + SX, Benalaxyl M + SX, Furaraxyl + SX, Metalaxyl + SX, Metalaxyl M + SX, Oxadixyl + SX, Offrace + SX,
Benodanyl + SX, benzobindiflupyr + SX, bixafen + SX, boscalid + SX, carboxin + SX, fenfram + SX, fluopyram + SX, flutolanil + SX, floxapyradod + SX, furametopyl + SX, isophetamide + SX, isopyrazam + SX, propyram + SX, propyram + SX, propyram + SX , Penthiopyrad + SX, penflufen + SX, sedaxane + SX, tifluzamide + SX, pyraziflumide + SX, pidiflumethofene + SX, bactericidal compound β1 + SX, bactericidal compound β2 + SX, bactericidal compound β3 + SX, bactericidal compound β4 + SX, bactericidal compound β5 + SX,
Benomyl + SX, carbendazim + SX, fuberidazole + SX, thiabendazole + SX, thiophanate + SX, thiophanatemethyl + SX, dietofencarb + SX, zoxamide + SX, ethaboxam + SX,
Felbum + SX, Manzeb + SX, Manneb + SX, Methylam + SX, Propineb + SX, Thiuram + SX, Dinebu and Diram + SX, Captan + SX, Captahole + SX, Holpet + SX, Chlorothalonyl + SX, Tolyl fluanid + SX, Guazatine X , Dithianon + SX, quinomethionate + SX, fluorimide + SX,
Dimethomorph + SX, Flumorph + SX, Pyrimorph + SX, Bench Avaricarb + SX, Bench Avaricarb isopropyl + SX, Iprovaricarb + SX, Varifenalate + SX, Mandipropamide + SX,
Fenpiclonyl + SX, fludioxonil + SX, clozolinate + SX, iprodione + SX, procymidone + SX, vinclozoline + SX, tolcrofosmethyl + SX, oxathiapiproline + SX, picalbutrazox + SX, flupicoride + SX, silthiofam + SX.

The composition of the present invention may be a mixture of the present pyridazine compound and the present compound, but usually the present pyridazine compound and the present compound are mixed with an inert carrier such as a solid carrier, a liquid carrier or a gaseous carrier. If necessary, add surfactants and other formulation adjuvants, emulsions, oils, powders, granules, wettable powders, flowables, microcapsules, aerosols, smokers, poison baits , Resin preparations, shampoos, pasty preparations, foams, carbon dioxide preparations, tablets and the like. These preparations may be used after being processed into mosquito coils, electric mosquito mats, liquid mosquito traps, fumigants, fumigants, sheet preparations, spot-on agents, or oral treatments.
The total amount of the present pyridazine compound and the present compound in the composition of the present invention is generally 0.1% to 100% by weight, preferably 0.2 to 90% by weight, more preferably 1 to 80% by weight.

  Examples of solid carriers used for formulation include clays (kaolin clay, diatomaceous earth, bentonite, fusami clay, acidic clay), synthetic hydrous silicon oxide, talc, ceramics, and other inorganic minerals (sericite, quartz, sulfur). , Activated carbon, calcium carbonate, hydrated silica, etc.), fine powders and granules of chemical fertilizers (ammonium sulfate, phosphorous acid, ammonium nitrate, urea, ammonium chloride, etc.), and synthetic resins (polypropylene, polyacrylonitrile, polymethyl methacrylate) Polyester resins such as polyethylene terephthalate, nylon resins such as nylon-6, nylon-11, and nylon-66, polyamide resins, polyvinyl chloride, polyvinylidene chloride, and vinyl chloride-propylene copolymers).

  Examples of the liquid carrier include water, alcohols (methanol, ethanol, isopropyl alcohol, butanol, hexanol, benzyl alcohol, ethylene glycol, propylene glycol, phenoxyethanol, etc.), ketones (acetone, methyl ethyl ketone, cyclohexanone, etc.), aromatic hydrocarbons (Toluene, xylene, ethylbenzene, dodecylbenzene, phenylxylylethane, methylnaphthalene, etc.), aliphatic hydrocarbons (hexane, cyclohexane, kerosene, light oil, etc.), esters (ethyl acetate, butyl acetate, isopropyl myristate, Ethyl oleate, diisopropyl adipate, diisobutyl adipate, propylene glycol monomethyl ether acetate, etc.), nitriles (acetonitrile, isobutyro Tolyl), ethers (diisopropyl ether, 1,4-dioxane, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether, 3-methoxy-3-methyl-1-butanol, etc. ), Amides (DMF, N, N-dimethylacetamide, etc.), sulfoxides (DMSO, etc.), propylene carbonate and vegetable oils (soybean oil, cottonseed oil, etc.).

  Examples of the gaseous carrier include fluorocarbon, butane gas, LPG (liquefied petroleum gas), dimethyl ether, and carbon dioxide gas.

  Examples of the surfactant include nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, and polyethylene glycol fatty acid ester, and anions such as alkyl sulfonate, alkyl benzene sulfonate, and alkyl sulfate. Surfactant is mentioned.

  Examples of other adjuvants for preparation include fixing agents, dispersants, colorants and stabilizers, such as casein, gelatin, saccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, Synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.), PAP (isopropyl acid phosphate), BHT (2,6-di-tert-butyl-4-methylphenol), BHA (2-tert- And a mixture of butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol).

Examples of the base material of the resin preparation include vinyl chloride polymers and polyurethanes. These base materials include phthalic acid esters (dimethyl phthalate, dioctyl phthalate, etc.), adipic acid esters, if necessary. A plasticizer such as stearic acid may be added. The resin formulation is obtained by kneading the present pyridazine compound and the present compound into the base material using a general kneading apparatus, and then performing molding such as injection molding, extrusion molding, press molding, and the like, if necessary. It can be processed into a resin formulation having a plate shape, a film shape, a tape shape, a net shape, a string shape or the like through processing steps such as molding and cutting. These resin preparations are processed into, for example, animal collars, animal ear tags, sheet preparations, attraction strings, and horticultural supports.
Examples of the bait base include cereal flour, vegetable oil, sugar, crystalline cellulose, and, if necessary, antioxidants such as dibutylhydroxytoluene and nordihydroguaiaretic acid, preservatives such as dehydroacetic acid, Additives such as chili powder and other food accident prevention agents for children and pets, cheese flavor, onion flavor, peanut oil and other pest-attracting flavors.

  The content ratio of the present pyridazine compound and the present compound in the composition of the present invention is not particularly limited, but the ratio of the content of the present pyridazine compound and one or more compounds selected from the group (a). Is preferably in the range of 100: 1 to 1: 100 by weight, particularly preferably in the range of 10: 1 to 1:10, and one or more compounds selected from the present pyridazine compounds and the group (b) The content ratio is preferably in the range of 10,000: 1 to 1: 100 by weight, particularly preferably in the range of 1000: 1 to 1:10.

  The pest control method of the present invention is performed by applying an effective amount of the composition of the present invention to pests directly and / or to pest habitats (plants, soil, households, animal bodies, etc.). .

  Examples of the application method of the composition of the present invention include application to plants, application to soil where plants are cultivated, and application to plant seeds or bulbs. Examples of application to plants include application to plant foliage, flower vases, seedlings or ears. Examples of the application to soil for cultivating plants include application to soil before planting or after planting. Examples of application to plant seeds or bulbs include seed disinfection, seed soaking, and seed coating. In addition, this pyridazine compound and this compound may be applied separately, and before and after seeding or seeding bulbs to which either the present pyridazine compound or this compound is attached to the soil, the remaining one is applied to the soil. Also good.

  Specific examples of application to plant foliage, flower vases, seedlings or ears include application methods applied to the surface of plants such as foliage spray, trunk spray, and the like. Examples include a method of spraying the entire vase or the whole plant at the flowering time, and a method of spraying the head or the whole plant at the heading time for cereals.

In addition, the method of applying to the soil before or after planting is, for example, by applying the composition of the present invention to the rhizosphere of a crop to be protected from damage such as feeding by pests. Or a method of controlling pests such as feeding plants by osmotic transfer of the present pyridazine compound and the present compound from the root to the inside of the plant body.
Specifically, for example, planting treatment (planting hole spraying, planting hole treatment soil mixing), plant source processing (stock source spraying, strain source soil mixing, strain source irrigation, late seedling stage plant source processing), planting groove processing (Groove spraying, grooving soil admixture), cropping treatment (growing sprinkling, cropping soil blending, growing season cropping spraying), sowing cropping treatment (sowing cropping spraying, sowing cropping soil blending) , Whole surface treatment (overall soil application, whole surface soil admixture), side strip treatment, water surface treatment (water surface application, water surface application after submergence), other soil application treatment (growth season foliar leaf surface application, under the crown or around the trunk, Soil surface spraying, soil surface mixing, sowing hole spraying, buttocks ground surface spraying, inter-strain spraying), and other irrigation treatments (soil irrigation, seedling irrigation, chemical solution injection treatment, local irrigation, chemical drip irrigation, chemical ligation), Nursery box processing (nursery box spraying, seedling box irrigation, seedling box chemical solution watering), seedling tray processing ( Seedling tray spraying, seedling tray irrigation, seedling tray chemical solution flooding), seedling treatment (seedbed spraying, seedbed irrigation, water seedling substitute seedbed spraying, seedling soaking), bed soil mixing treatment (bed soil mixing, bed soil mixing before sowing, seeding) Application before soil covering, after soil covering after seeding, mixing with soil covering) and other treatments (mixing soil, mixing, topsoil mixing, rain soil mixing, planting position treatment, granule inflorescence spraying, paste fertilizer mixing).

In the present invention, the plant seed means plant seed in a state before being sown in the soil or the culture medium, and the bulb is a bulb of the plant in a state before being planted in the soil or the culture medium. It means tubers, rhizomes, stem fragments, seed pods and tuberous roots. The method of applying the composition of the present invention to plant seeds or bulbs is, for example, a method of controlling pests by applying the composition of the present invention directly to plant seeds or bulbs to be protected from damage such as feeding by pests. A method for controlling pests that feed on seeds and the like by applying the composition of the present invention in the vicinity of plant seeds or bulbs; or osmotic transfer of the pyridazine compound and the compound from the plant seeds or bulbs into the plant body; It is a method for controlling pests such as feeding plants, specifically, for example, spraying treatment, smearing treatment, dipping treatment, impregnation treatment, coating treatment, film coating treatment, pellet coating treatment Can be mentioned. The plant seed or bulb of the present invention is a plant seed or bulb obtained by attaching an effective amount of the composition of the present invention by these methods, and retains an effective amount of the composition of the present invention.
When the composition of the present invention is applied to plant seeds or bulbs, the amount of the pyridazine compound applied is usually 0.001 to 100 g, preferably 0.02 to 20 g, per 1 kg of plant seeds or bulbs. The dose is usually 0.000001-50 g, preferably 0.0001-30 g per kg of plant seeds or bulbs.

  Examples of the pests for which the composition of the present invention is effective include harmful insects, harmful mites, harmful nematodes, and phytopathogenic fungi such as filamentous fungi and bacteria. Specific examples of such pests include the following.

  Hemiptera: insects such as Japanese brown planthopper (Laodelphax striatellus), yellow planthopper (Nilaparvata lugens), white-tailed planthopper (Sogatella furcifera), corn planter (Peregrinus maidis); leafhopper green (Nephotettix cincticeps) (Nephotettix nigropictus), Recilia dorsalis, Empoasca onukii, Potato leaf hopper (Empoasca fabae), Corn leaf hopper (Dalbulus maidis), Sugarcane froghopper (Mahanarug bugarcane, Mahanarug bugarcane) ), Leafhoppers (Cofana spectra), leafhoppers such as Nephotettix nigropictus; cotton aphids (Aphis gossypii), peach aphids (Myzus persicae), radish aphids (Brevicoryne) brassicae, Aphis spiraecola, Macrosiphum euphorbiae, Aulacorthum solani, Rhopalosiphum padi, Prix, Citrus aura Soybean aphids (Aphis glycines Matsumura), corn aphids (Rhopalosiphum maidis), brown aphids (Tetraneura nigriabdominalis), grape aphids (Viteus vitifoliae), Grape Phylloxera (Daktulosphaira vitifoliae), Pecan phylloxde (Pakyphylloxdeae) Aphids such as Phylloxera notabilis pergande), Southern pecan leaf phylloxera (Phylloxera russellae Stoetzel); Scotinophara lurida, Malayan rice black bug (Scotinophara coarctata), Aoku Stink bug (Nezara antennata), Togeshiraboshi stink bug (Eysarcoris parvus), Swan bug (Halyomorpha mista), Southern stink bug (Nezara viridula), Brown stink bug (Euschistus heros), Southern green stink bug (Nezara viridula), Red band stagger bug (Nezara viridula) (Piezodorus guildinii), Burrower brown bug (Scaptocoris castanea), Oebalus pugnax, Dichelops melacanthus and other stink bugs; Ganoderma reptiles such as Trigonotylus caelestialium, Stenotus rubrovittatus, Turned plant bug (Lygus lineolaris), Chinchi bug (Blissus leucopterus leucopterus) ) Tobacco Kona Whitefly (Bemisia tabaci), citrus whitefly (Dialeurodes citri), whitefly (Aleurocanthus spiniferus) and other whitefly species; Ceroplastes rubens), Icerya purchasi, Fujico scale insect (Planococcus kraunhiae), stag beetle scale (Pseudococcus longispinis), stag beetle scale (Pseudaulacaspis pentagona), tattle-my-bug Diaphorina citri, Psylla pyrisuga, Bactericerca cockerelli, and other killer whales; Stephanitis nasi and other hornworms; Cimex lectularius Lice acids and Giant Cicada (Quesada gigas).

  Lepidopterous insects: Chilo suppressalis, Darkheaded stem borer (Chilo polychrysus), Sankameiga (Tryporyza incertulas), Shiromecho (Scirpophaga innotata), Yellow stem borer (Scirpophaga incertulas), Pink borer (Sellaamiupela, alga (Cnaphalocrocis medinalis), Rice leafroller (Marasmia patnalis), Inasoteki maki (Marasmia exigua), Noarcha derogata, Plodia interpunctella, Ostrinia furnacalis unai tia (Ostrinia furnacalis) ), Rice case worm (Nymphula depunctalis), Marasmia genus, Hop vine borer (Hydraecia immanis), European corn borer (Ostrinia nubilalis), Lesser cornstalk borer (Elasmopalpus lignosellus), Bean Shoot Borer (Epinotia atraanes borer (Epinotia atramaeas) ), Giant Sugarcane bor er (Telchin licus), etc .; Spodoptera litura, Spodoptera exigua, Pseudaletia separata, Mamestra brassicae, Sesamia inferens, Spodamia opt (Spodoptera frugiperda), Spodoptera exempta, Agrotis ipsilon, Tamanagiwawa (Plusia nigrisigna), Soybean looper (Pseudoplusia includens), Trichopulcia, Heliothis virescens Species of the genus Helicoberpa, Velvetbean caterpillar (Anticarsia gammatalis), Cotton leafworm (Alabama argillacea) and other moths; White butterflies such as Pieris rapae; Adoxofies genus, Grapholita molesta, Leguminivora glycinivorella), Azukisayamushiga (Matsumuraeses azukivora), apple Coca summer fruit tortrix (Adoxophyes orana fasciata), smaller tea tortrix (Adoxophyes honmai. ), Chamonaki (Homona magnanima), Midchipakumumonaki (Archips fuscocupreanus), Codlinga (Cydia pomonella), etc .; Sink moths such as borer (Ecdytolopha aurantiana); Coffee leaf miner (Leucoptera coffeela); gossypiella) Potatoes such as potato moth (Phthorimaea operculella); Hitorigers such as Hyphantria cunea.

  Common pests: Citrus thrips (Frankliniella occidentalis), Southern thrips (Thrips parmi), Scirtothrips dorsalis, Thrips tabaci, identifica ella Thrips such as the rice thrips (Haplothrips aculeatus) and the rice thrips (Stenchaetothrips biformis).

  Diptera: insect fly (Delia platura), onion fly (Delia antiqua), sugar beet root maggot (Tetanops myopaeformis) and other species; Agromyza oryzae; ), Leafworms (Liriomyza trifolii), leafworms (Chromatomyia horticola), etc .; leafhoppers (Chlorops oryzae), etc .; (Hydrellia philippina) Hydrellia sasakii, etc .; Drosophila, Drosophila, Drosophila, such as Megaselia spiracularis; Drosophila, such as Clogmia albipunctata; Fly flies; fly flies such as Heyetiola destructor and Oreseolia oryzae; hammer fly such as Diopsis macrophthalma; common cranefly (Tipula oleracea) and crane fly such as European cranefly (Tipula paludosa).

  Coleoptera: Western corn root worm (Diabrotica virgifera virgifera), Southern corn root worm (Diabrotica undecimpunctata howardi), Northern corn root worm (Diabrotica barberi), Mexican corn root worm (Diabrotica virgifera zeae), Banded cucumber bar balte (Teabrotte balte) ), San Antonio beetle (Diabrotica speciosa), Cucurbit Beetle (Diabrotica speciosa), bean leaf beetle (Cerotoma trifurcata), cereal leaf beetle (Oulema melanopus), cucumber leaf beetle (Aulacophora femoralis), pheasant leaf beetle (Phyllotreta dectriata decrimata) ), Oedema oryzae, Colaspis brunnea, Chaetocnema pulicaria, Potato flare beetle (Epitrix cucumeris), Leaf beetles (Dicladispa armigera), Seedcorn beetle (Stenolophus lecontei), Slender seedcorn beetle (Clivinia impressifrons), etc .; Carrot beetle (Bothynus gibbosus), Grape Colaspis (Colaspis brunnea), southern Corn leaf beetle (Myochrous denticollis), Holotrichia genus, June beetle (Phyllophaga crinita), etc. squameus), rice weevil (Lissorhoptrus oryzophilus), weevil weevil (Sphenophorus venatus), etc .; Weevil species such as us; Epiracunas such as Epilachna vigintioctopunctata; Stemworms such as Lyctus brunneus; Tomicus piniperda; ), Migdolus fryanus, etc .; Okinawa beetle (Melanotus okinawensis); Melanotus sp., Limonius sp., Conoderus sp., Ctenicera sp.);

  Insect pests: Locusta migratoria, Gryllotalpa africana, Moroccan grasshopper (Dociostaurus maroccanus), Australian grasshopper (Chortoicetes terminifera), Red locust (Nomadacris septemfasciata), Brown pardal (ust) melanorhodon), Italian Locust (Calliptamus italicus), Differential grasshopper (Melanoplus differentialis), Two striped grasshopper (Melanoplus bivittatus), Migratory grasshopper (Melanoplus sanguinipes), Red-Legged grasshopper (Melanoplus femurrubrum), Clearwingpel grass Grasshopper (Schistocerca gregaria), Yellow-winged locust (Gastrimargus musicus), Spur-throated locust (Austracris guttulosa), Spotted eel (Oxya yezoensis), Spotted eel (Oxya japonica), Thai winged locust (Patanga succitames) ticus), Emmacrickets (Teleogryllus emma), Mormon cricket (Anabrus simplex), etc.

Hymenopteran pests: bees such as Athalia rosae and Athalia japonica; fire ants;
Cockroach insects: German cockroach (Blattella germanica), Black cockroach (Periplaneta fuliginosa), American cockroach (Periplaneta americana), Great cockroach (Periplaneta brunnea), Great cockroach (Blatta orientalis).

  Termite insect pests: Yamato termite (Reticulitermes speratus), termite (Coptotermes formosanus), American white termite (Incisitermes minor), scallop termite (Cryptotermes domesticus), taiwan termite (Odontotermes formosanus), red ant termite (hunsterm termite) Glyptotermes satsumensis, Glyptotermes nakajimai, Gantptotermes fuscus, Glyptotermes kodamai, Guangptotermes kushimensis, Hoptermite amamianus), termite termites (Reticulitermes miyatakei), termites termites (Reticulitermes kanmonensis), termites termites (Nasutitermes takasagoensis), termites termites (Pericap) ritermes nitobei), Sinocapritermes mushae, Cornitermes cumulans, etc.

Ticks: spider mites (Tetranychus urticae), spider mites (Tetranychus kanzawai), citrus spider mites (Panonychus ulmi), spider mites (Southern spider mites (Brevipalpus phoenicis), etc.); Phyllocoptruta citri, Tomato rustic mite (Aculops lycopersici), Chinese rustic mite (Calacarus carinatus), Chinese cabbage mite (Acaphylla theavagrans), Green radish mite (Eriophyes chibaensis), Mite schist ticks Dust mites such as (Polyphagotarsonemus latus); spider mites such as the southern red spider mite (Brevipalpus phoenicis); spider mite; Haemaphysalis longicornis; Tick (Dermacentor taiwanicus), American dog ticks (Dermacentor variabilis), Yamato ticks (Ixodes ovatus), Schulz ticks (Ixodes persulcatus), Black-legged ticks (Ixodes scapularis), American tick ticks (Amblyomma americanum), ophilus tick Ticks such as Rhipicephalus sanguineus; tick such as Tyrophagus putrescentiae; Tyrophagus similis; hey D eruditus), crawfish tick (Cheyletus malaccensis), crayfish tick (Cheyletus moorei), crayfish tick (Cheyletiella yasguri), etc .; Spider mites such as Sacroptes scabiei); Leptotrombidium akamushi).
Spiders: Spiders such as Chiracanthium japonicum and Latrodectus hasseltii.
Lip and limb class: Thereuonema hilgendorfi, Scolopendra subspinipes, etc.
Double-legged class: Japanese red millipede (Oxidus gracilis), Japanese red millipede (Nedyopus tambanus).
Isopods: Armadillidium vulgare, etc.
Gastropoda: Limax marginatus, Limax flavus, Pomacea canaliculata, etc.

  Nematodes: Aphelenchoides basseyi from Aphelenchoides sp .; Pratylenchus sp., Pratylenchus brachyurus, Pratylenchus brachyurus neglectus); Meloidogyne javanica, Meloidogyne incognita, Meloidogyne hapla; Heterodera sp. (Globodera sp.) Potato cyst nematode (Globodera rostochiensis), Rotylenchulus reniformis, strawberry nematode (Nothotylenchus acris), Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans; Longidorus sp .; Xiphinema sp .; Trichodorus (Trichodorus sp.); Bursaphelenchus sp. )etc.

Plant pathogens: Rice blast (Magnaporthe grisea), sesame leaf blight (Cochliobolus miyabeanus), blight (Rhizoctonia solani), idiot seedling (Gibberella fujikuroi), yellow dwarf (Sclerophthora macrospora); wheat udon Disease (Erysiphe graminis), red mold (Fusarium graminearum, F.avenaceum, F.culmorum, Microdochium nivale), rust (Puccinia striiformis, P.graminis, P. recondita), red snow rot (Microdochium nivale, M. majus), Snow rot, Mycobacterium tuberculosis (Typhula sp.), Bare scab (Ustilago tritici), Nagusa scab (Tilletia caries, T. controversa), Eye rot (Pseudocercosporella herpotrichoides), Leaf blight (Septoria tritici) , Dry blight (Stagonospora nodorum), yellow spot (Pyrenophora tritici-repentis), Rhizoctonia solani, blight (Gaeumannomyces graminis); barley powdery mildew (Erysiphe graminis), red Mold disease (Fusar ium graminearum, F.avenaceum, F.culmorum, Microdochium nivale), rust disease (Puccinia striiformis, P.graminis, P.hordei), naked smut (Ustilago nuda), cloud disease (Rhynchosporium secalis), net leaf disease (Pyrenophora) teres), spot disease (Cochliobolus sativus), leafy leaf disease (Pyrenophora graminea), lambaria disease (Ramularia collo-cygni), Rhizoctonia solani (Rhizoctonia solani); corn rust (Puccinia sorghi), southern Rust (Puccinia polysora), soot rot (Setosphaeria turcica), tropical rust (Physopella zeae), sesame leaf blight (Cochliobolus heterostrophus), anthracnose (Colletotrichum graminicola), gray leaf spot (Cercospora zeae- maydis), brown spot disease (Kabatiella zeae), Faeosphaeria reef spot disease (Phaeosphaeria maydis), diplodia disease (Stenocarpella maydis, Stenocarpella macrospora), Stocro Tomato disease (Fusarium graminearum, Fusarium verticilioides, Colletotrichum graminicola), smut (Ustilago maydis); cotton anthracnose (Colletotrichum gossypii), mildew (Ramularia areola), black spot (Alternaria macrospora, A. gossypii), Black root rot disease caused by Thielaviopsis (Thielaviopsis basicola); coffee rust (Hemileia vastatrix); leaf spot disease (Cercospora coffeicola); rape myeloid disease (Sclerotinia sclerotiorum); black spot disease (Alternaria brassicae); Disease (Phoma lingam); sugarcane rust (Puccinia melanocephela, Puccinia kuehnii), smut (Ustilago scitaminea); sunflower rust (Puccinia helianthi), downy mildew (Plasmopara halstedii); citrus black spot tri (Dia) Common scab (Elsinoe fawcetti), fruit rot (Penicillium digitatum, P.italicum), plague (Phytophthora parasitica, Phytophthora citrophthora); apple moniliosis Monilinia mali), rot disease (Valsa ceratosperma), powdery mildew (Podosphaera leucotricha), spotted leaf disease (Alternaria alternata apple pathotype), black spot disease (Venturia inaequalis), anthracnose disease (Glomerella cingulata), brown spot disease (Diplocarpon mali) ), Ringworm (Botryosphaeria berengeriana), plague (Phytophtora cactorum); pear black spot (Venturia nashicola, V.pirina), black spot (Alternaria alternata Japanese pear pathotype), red star (Gymnosporangium haraeanum); peach ash Star disease (Monilinia fructicola), black scab (Cladosporium carpophilum), phomopsis sp. (Phomopsis sp.); Grape black rot (Elsinoe ampelina), late rot (Glomerella cingulata), powdery mildew (Uncinula necator), rust Diseases (Phakopsora ampelopsidis), blacklot disease (Guignardia bidwellii), downy mildew (Plasmopara viticola); oyster anthracnose (Gloeosporium kaki), deciduous disease (Cercospora kaki, Mycosphaerella) nawae); cucurbit (Colletotrichum lagenarium), powdery mildew (Sphaerotheca fuliginea), vine blight (Didymella bryoniae), brown spot (Corynespora cassiicola), vine split (Fusarium oxysporum), downy mildew ( Pseudoperonospora cubensis), plague (Phytophthora sp.), Seedling blight (Pythium sp.); Tomato ring-rot (Alternaria solani), leaf mold (Cladosporium fulvum), subtilis (Pseudocercospora fuligena), plague (Phytophthora) infestans), powdery mildew (Leveillula taurica); eggplant brown spot (Phomopsis vexans), powdery mildew (Erysiphe cichoracearum); cruciferous vegetable black spot (Alternaria japonica), white spot (Cercosporella brassicae), root bump Disease (Plasmodiophora brassicae), downy mildew (Peronospora parasitica); spring onion rust (Puccinia allii); soybean purpura (Cercospora kikuchii), black scab (Elsinoe glycines), black spot (Diaporthe phaseolorum var.sojae) , Rust (Phakopsora pachyrhizi), brown rot (Corynespora cassiicola), anthrax (Colletotrithum glycines, C. truncatum), leaf rot (Rhizoctonia solani), brown rot (Septoria glycines), spot disease (Cercospora sojina) Sclerotinia sclerotiorum, powdery mildew (Microsphaera diffusa), stem rot (Phytophthora sojae), downy mildew (Peronospora manshurica), sudden death (Fusarium virguliforme); kidney bean, Sclerotinia sclerotiorum , Rust disease (Uromyces appendiculatus), horn spot disease (Phaeoisariopsis griseola), anthracnose disease (Colletotrichum lindemthianum), peanut black astringency (Cercospora personata), brown spot disease (Cercospora arachidicola), white silk disease (Sclerotium rolfsii) Pea powdery mildew (Erysiphe pisi); potato summer plague (Alternaria solani), plague (Phytophthora infestans), scarlet rot (Phytophthora erythroseptica), powdery scab (Spongospora) subterranean f.sp.subterranea), half body wilt disease (Verticillium albo-atrum, V.dahliae, V.nigrescens); Strawberry powdery mildew (Sphaerotheca humuli); Cha net rot (Exobasidium reticulatum), white scab (Elsinoe) leucospila), ring spot disease (Pestalotiopsis sp.), anthracnose (Colletotrichum theae-sinensis); tobacco scab (Alternaria longipes), anthracnose (Colletotrichum tabacum), downy mildew (Peronospora tabacina), plague (Phytophthora) nicotianae); brown spot of sugar beet (Cercospora beticola), leaf rot (Thanatephorus cucumeris), root rot (Thanatephorus cucumeris), black root (Aphanomyces cochlioides); rose scab (Diplocarpon rosae) pannosa); brown spot of chrysanthemum (Septoria chrysanthemi-indici), white rust (Puccinia horiana); white leaf blight of onion (Botrytis cinerea, B. byssoidea, B. squamosa), gray rot (Botrytis alli), Sclerotial rot (Botrytis squamosa); various crops of gray mold disease (Botrytis cinerea), mycorrhizal disease (Sclerotinia sclerotiorum); radish black spot disease (Alternaria brassicicola); buckwheat dollar spot disease (Sclerotinia homeocarpa); Large patch disease (Rhizoctonia solani); and banana sigatoka disease (Mycosphaerella fijiensis, Mycosphaerella musicola).
Seed disease or early growth of various crops caused by Aspergillus, Penicillium, Fusarium, Gibberella, Tricoderma, Thielaviopsis, Rhizopus, Mucor, Corticium, Phoma, Rhizoctonia, and Diplodia Disease. Viral diseases of various crops mediated by Polymixa genus or Olpidium genus.
Rice seed blight (Burkholderia plantarii); Cucumber spotted bacterial disease (Pseudomonas syringae pv. Lachrymans); Eggplant blight (Ralstonia solanacearum); Citrus scab (Xanthomonas citiri); carotovora) etc.

  Target harmful insects, harmful mites, harmful nematodes and phytopathogenic fungi are insects, mites, insecticides, acaricides, nematicides, fungicides with reduced drug sensitivity or developed drug resistance Nematodes and phytopathogenic fungi may be used. However, if the drug sensitivity is significantly reduced or the drug resistance is greatly developed, insecticidal, acaricidal, nematicidal, bactericidal agents other than the target insecticidal, acaricidal, nematicidal, bactericidal agents The use of a composition of the invention comprising

  The composition of the present invention can also be used to protect plants from plant diseases caused by insect-borne viruses.

  Examples of plant diseases caused by insect-borne viruses having the control effect of the composition of the present invention include the following.

  Rice dwarf disease (Rice waika virus), Tundra disease (Rice tungro spherical virus, Rice tungro bacilliform virus), Rice grassy stunt disease (Rice grassy stunt virus), Rice ragged stunt virus, rice stripe leaf blight Diseases (Rice stripe virus), rice black streaked dwarf virus, rice southern black-streaked dwarf virus, rice gall dwarf virus, rice leaf blight ( Rice hoja blanca virus), White leaf desease of rice, Yellow dwarf virus, Red disease (Rice penyakit merah virus), Rice yellow stunt virus, Transition yellowing Disease (Rice transitory yellowing virus), rice yellow disease (Rice Yellow Mottle Virus), rice necrosis mosaic virus, rice dwarf stunt virus, northern wheat mosaic disease (No rthern Cereal Mosaic Virus), Barley Yellow Dwarf Virus, Wheat yellow dwarf virus, Oat sterile dwarf (Oat sterile dwarf virus), Wheat streak mosaic (Wheat streak mosaic virus), corn mosaic Maize dwarf mosaic virus, Maize stripe disease (maize stripe tenuivirus), Maize chlorotic dwarf (Maize chlorotic dwarf virus), Maize chlorotic mottle (maize chlorotic mottle virus), Maize rayado fino (maize rayado fino marafivirus), Corn stunt ( Corn stunt spiroplasma), Maize bushy stunt (Maize bushy stunt phytoplasma), sugarcane mosaic disease (Sugarcane mosaic virus), soybean mild mosaic virus, mosaic disease (Alfalfa Mosaic Virus, Bean yellow-spot mosaic virus, Soybean mosaic virus, Bean yellow mosaic virus, Cowpea severe mosaic virus, Soybean virus disease (Broad bean wilt virus, Bean common mosaic virus, Peanu t stunt virus, Southern bean mosaic virus), soybean dwarf luteovirus, Milk-vetch dwarf luteovirus, Bean-pod mottle (Bean-pod mottle virus), Brazilian bud blight (Tobbaco streak virus), Cowpea chlorotic mottle (Cowpea chlorotic mottle), Mung bean yellow mosaic (Mung bean yellow mosaic virus), Peanut stripe (Peanut stripe mottle), Soybean crinkle leaf (Soybean crinkle leaf virus), Soybean severe stunt (Soybean severe stunt virus), Tomato yellow disease (Tomato chlorosis virus), Tomato spotted wilt virus, Tomato yellow leaf curl virus, Melon yellow spot virus, Pumpkin mosaic disease (Watermelon mosaic virus), dwarf disease (Cucumber mosaic virus), zucchini yellow mosaic virus, turnip mosaic virus, Cucurbit chlorotic yellows virus Capsicum chlorosis virus, Beet pseudo yellows virus, Chrysanthemum stem necrosis virus, Impatiens necrotic spot virus, Iris yellow spot (Iris Yellow spot virus, sweet potato internal cork virus, sweet potato shukuyo mosaic virus, polymixa genus or Olpidium genus, etc.

When the composition of the present invention is used for pest control, its application rate can be varied widely depending on the application time, application location, application method, etc., but in general, the present pyridazine compound and the present compound The total amount is usually 1 to 10,000 g per 10,000 m ² . When the composition of the present invention is formulated into an emulsion, a wettable powder, a flowable agent, etc., the present pyridazine compound and the present compound usually have a total concentration of 0.01 to 10,000 ppm. It is diluted with water and applied, and granules, powders and the like are usually applied as they are.

Examples of plants that can use the composition of the present invention include the following.
Corn, rice, wheat, barley, rye, triticale, oat, sorghum, cotton, soybean, groundnut (peanut), cypress (green beans), lentil, azuki bean, cowpea, mung bean, ladamame, safflower beans, bamboo shoots, moss bean, tepareen beans , Peas, chickpeas, lentils, lupines, pigeons, alfalfa, buckwheat, sugar beet, rape, sunflower, sugarcane, tobacco, etc.
Eggplant vegetable (eggplant, tomato, pepper, pepper, bell pepper, potato), cucumber vegetable (cucumber, pumpkin, zucchini, watermelon, melon, squash, etc.), cruciferous vegetable (radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, mustard, broccoli, cauliflower, etc.), Asteraceae vegetables (burdock, garlic, artichoke, lettuce, etc.), liliaceae vegetables (eg, leek, onion, garlic, asparagus), celery family vegetables (carrot, parsley, celery) , American Bow Fu etc.), red crustacean vegetables (spinach, chard, etc.), perilla vegetables (shiso, mint, basil, lavender etc.), vegetables such as strawberry, sweet potato, yam, taro,
Fruits (apples, pears, Japanese pears, quince, quince, etc.), nuclear fruits (peaches, plums, nectarines, ume, sweet cherry, apricots, prunes, etc.), citrus (citrus oranges, oranges, lemons, limes, grapefruits, etc.) , Nuts (chestnuts, walnuts, hazel, almonds, pistachios, cashew nuts, macadamia nuts, etc.), berries (blueberries, cranberries, blackberries, raspberries, etc.), grapes, oysters, olives, loquats, bananas, coffee, dates, Fruit trees such as coconut,
Tea, mulberry, flowering trees, roadside trees (ash, birch, dogwood, eucalyptus, ginkgo, lilac, maple, oak, poplar, redwood, fus, sycamore, zelkova, kurobe, mominoki, tsuga, nezu, pine, spruce, yew), Flower buds, houseplants, ferns, pastures.

The above-described plant is not limited as long as it is a variety that is generally cultivated. Such varieties of plants include plants to which one or more useful traits have been conferred by genetic breeding techniques or genetic recombination techniques (genetically modified plants) and stack varieties in which they are crossed.
Such useful traits include herbicide resistance, pest resistance, disease resistance, stress resistance, and quality improvement of fatty acid residue composition modified crops of fats and oils.

  Examples of such a genetically modified plant include, for example, genetic recombination in an electronic information site (http://www.isaaa.org/) of the International Agri-Bio Service Company (INTERNATION SERVICE for the ACQUISITION of AGRI-BIOTECH APPLICATIONS, ISAAA). Plants listed in the crop registration database (GM APPROVAL DATABASE) are listed. More specifically, plants that have been given environmental stress resistance, disease resistance, herbicide resistance, pest resistance, etc. by genetic recombination techniques, or traits related to growth and yield, product quality, fertility traits, etc. It may be a modified plant.

Plants that have been given herbicide tolerance by genetic recombination technology include protoporphyrinogen oxidase (hereinafter abbreviated as PPO) herbicides such as flumioxazin, 4-hydroxyphenylpyruvate diacids such as isoxaflutol and mesotrione. Oxygenase (hereinafter abbreviated as HPPD) inhibitors, acetolactate synthase (hereinafter abbreviated as ALS) inhibitors such as imazetapyr and thifensulfuronmethyl, 5-enolpyruvylshikimate-3-phosphate synthase such as glyphosate ( (Hereinafter abbreviated as EPSP) inhibitors, glutamine synthetase inhibitors such as glufosinate, auxin-type herbicides such as 2,4-D and dicamba, and plants to which resistance to herbicides such as bromoxynil has been conferred by genetic recombination technology included.
Examples of plants to which herbicide tolerance has been imparted by gene recombination technology include glyphosate-resistant EPSPS gene (CP4 epsps) derived from Agrobacterium tumefaciens strain CP4, glyphosate metabolizing enzyme derived from Bacillus licheniformis (Glyphosate N-acetyl transferase) gene, whose activity is enhanced by shuffling technology, glyphosate metabolic enzyme genes (gat4601, gt6421), glyphosate metabolic enzyme (glyphosate oxidase gene, goxv247) derived from Ochrobacterum strain LBAA Or maize-derived glyphosate tolerance mutation EPSPS gene (mepsps, 2mepsps) having has one or more of the introduced glyphosate tolerant transgenic plants and the like. Maize (Zea mays L.), Soybean (Glycine max L.), Cotton (Gossypium hirsutum L.), Sugar beet (Beta vulgaris), Canola (Brassica napus, Brassica rapa), Alfalfa .), Wheat (Triticum aestivum), creeping bentgrass (Agrossis tolonifera) and other plants, there are glyphosate-resistant genetically modified varieties.
Several glyphosate-tolerant transgenic plants are commercially available. For example, genetically modified plants that express glyphosate-resistant EPSPS derived from Agrobacterium are trade names including Roundup Ready (registered trademark) and express glyphosate-metabolizing enzyme derived from Bacillus with enhanced metabolic activity by shuffling technology Genetically modified plants are trade names such as Optimum (registered trademark) GAT (registered trademark), Optimum (registered trademark) Gly canola, and transgenic plants expressing EPSPS having a glyphosate-resistant mutation derived from corn are GlyTol (registered trademark). ) Is already sold under the product name.
Similarly, as an example of a plant to which herbicide tolerance has been imparted by genetic recombination technology, phosphinothricin N-acetyltransferase, a glufosinate metabolizing enzyme derived from Streptomyces hygroscopicus, Phosphithricin N-acetyltransferase, A gene (bar), a phosphinothricin N-acetyltransferase gene (pat), which is a glufosinate metabolizing enzyme derived from Streptomyces viriochromogenes, or a glufosinate-tolerant transgenic plant introduced with a synthesized pat gene or the like There is. There are glufosinate-resistant transgenic varieties such as corn, soybean, cotton, canola, rice (Oryza sativa L.), sugar beet, chicory (Cichorium intybus) and the like.
Several glufosinate-tolerant transgenic plants are commercially available. Genetically modified plants that express glufosinate metabolizing enzymes (bar, pat) derived from Streptomyces are already sold under trade names including LibertyLink (registered trademark).
Similarly, as an example of a plant to which herbicide tolerance has been imparted by gene recombination technology, bromoxynyl-tolerant gene recombination in which a nitrilase gene (bxn), which is a bromoxynyl-metabolizing enzyme derived from Klebsiella pneumoniae subsp. Ozaenae, has been introduced. There are plants. Bromoxinyl-resistant genetically modified varieties are produced in plants such as canola, cotton, tobacco (Nicotiana tabacum L.), and are already sold under trade names including Navigator (registered trademark) canola or BXN (registered trademark) .
Similarly, as an example of a plant to which herbicide tolerance has been imparted by gene recombination technology, a genetically modified carnation (Dianthus caryophyllus) into which an ALS herbicide-tolerant ALS gene (surB, S4-HrA) derived from tobacco has been introduced as a selection marker ) In addition, a transgenic flax (Linum usitistisumum L.) into which an ALS herbicide-resistant ALS gene derived from Arabidopsis thaliana has been introduced has been developed under the trade name CDC Trifid Flax. A genetically modified soybean introduced with an ALS herbicide-tolerant ALS gene (csr1-2) derived from Arabidopsis thaliana has been developed under the name of Culture (registered trademark). Furthermore, transgenic corn resistant to sulfonylurea and imidazolinone herbicides introduced with corn-derived ALS herbicide-resistant ALS gene (zm-hr), soybean-derived ALS herbicide-resistant ALS gene (gm- There are genetically modified soybeans that are resistant to sulfonylurea herbicides introduced with fra).
Similarly, as an example of a plant to which herbicide resistance has been imparted by genetic recombination technology, an isoxaflutol resistant gene set into which an HPPD herbicide-resistant HPPD gene (hppdPFW336) derived from Pseudomonas fluorescens strain A32 has been introduced. There are modified soybeans and mesotrione resistant genetically modified soybeans introduced with HPPD gene (avhppd-03) derived from oat (Avena sativa).
Similarly, examples of plants to which herbicide tolerance has been imparted by genetic recombination techniques include allyloxyalkanoate dioxygenase, a 2,4-D metabolic enzyme derived from Sphingobium herbicidovorans. ) 2,4-D resistance into which the gene (aad-1) or the allyloxyalkanoate dioxygenase gene (aad-12), which is a 2,4-D metabolic enzyme derived from Delftia acidovorans, has been introduced GM, GM soybean, GM cotton, etc., some of which have been developed under the trade names of Enlist (registered trademark) Maize and Enlist (registered trademark) Soybean. Also, there are dicamba-resistant genetically modified soybeans, transgenic cottons and the like into which a dicamba monooxygenase gene (dmo) introduced as a dicamba metabolizing enzyme derived from Stenotrophomonas maltophilia strain DI-6 is introduced. is there.
Similarly, examples of plants that have been rendered tolerant to two or more herbicides by genetic engineering techniques include transgenic cotton that is resistant to both glyphosate and glufosinate, and genetically modified maize that is GlyTol® LibertyLink. (Registered trademark), Round Ready (registered trademark) LibertyLink (registered trademark) Maize is already sold under the trade name. In addition, a genetically modified soybean resistant to both glufosinate and 2,4-D was developed under the trade name Enlist (registered trademark) Soybean, and genetically modified cotton resistant to both glufosinate and 2,4-D. There is also. A genetically modified soybean that is resistant to both glyphosate and dicamba has been developed under the trade name Genuity (R) Roundup Ready (R) 2 Xtend (R). Genetically modified maize, soybean, which is resistant to both glyphosate and ALS inhibitors, has been developed under the trade name Optimum® GAT®. In addition, transgenic cotton resistant to both glufosinate and dicamba, transgenic corn resistant to both glyphosate and 2,4-D, transgenic soybean resistant to both glyphosate and HPPD herbicide Has also been developed. In addition, genetically modified soybeans that are resistant to three herbicides, glyphosate, glufosinate and 2,4-D, have also been developed.

Plants to which pest resistance has been imparted by gene recombination technology include plants to which resistance to lepidopterous insects, Coleoptera insects, multiple order insects, nematodes and the like are imparted.
As an example of a plant imparted with resistance against lepidopteran insects by genetic recombination technology, it encodes delta-endotoxin, which is an insecticidal protein derived from soil bacteria Bacillus thuringiensis (hereinafter abbreviated as Bt) And transgenic plants such as corn, soybean, cotton, rice, Populus (Populus sp.), Tomato (Lycopersicon esculentum) and eggplant (Solanum melongena). Cry1A, Cry1Ab, modified Cry1Ab (partially deleted Cry1Ab), Cry1Ac, Cry1Ab-Ac (a hybrid protein in which Cry1Ab and Cry1Ac are fused), Cry1C, Cry1F , Cry1Fa2 (modified cry1F), moCry1F (modified Cry1F), Cry1A. 105 (a hybrid protein in which Cry1Ab, Cry1Ac, and Cry1F are fused), Cry2Ab2, Cry2Ae, Cry9C, Vip3A, Vip3Aa20, and the like.
Examples of plants that have been given resistance to Coleoptera by genetic recombination technology include genetic recombination of maize, potato, etc., into which a gene encoding delta-endotoxin, an insecticidal protein derived from soil bacteria, Bt bacteria is introduced. There are plants. Examples of delta-endotoxins that confer resistance to Coleoptera insects include Cry3A, mCry3A (modified Cry3A), Cry3Bb1, Cry34Ab1, and Cry35Ab1.
As an example of a plant imparted with resistance to multiple insects by gene recombination technology, a gene set introduced with a synthetic gene encoding a hybrid protein eCry3.1Ab fused with Cry3A and Cry1Ab derived from soil bacteria Bt Transgenic corn, genetically modified cotton introduced with a gene encoding trypsin inhibitor CpTI derived from cowpea (Vigna unguicula), a gene set introduced with a gene encoding API that is protease inhibitor protein A derived from Kwai (Sagitaria sagittifolia) There is a replacement poplar.
Insecticidal proteins that impart pest resistance to plants include hybrid proteins of the above-mentioned insecticidal proteins, partially missing proteins, and modified proteins. The hybrid protein is produced by a combination of different domains of a plurality of insecticidal proteins, using genetic recombination technology, and Cry1Ab-Ac or Cry1A. 105 etc. are known. As a protein lacking a part, Cry1Ab and the like lacking a part of the amino acid sequence are known. Examples of the modified protein include proteins in which one or more amino acids of natural delta-endotoxin are substituted, and Cry1Fa2, moCry1F, mCry3A and the like are known.
In addition, as insecticidal proteins that impart pest resistance to plants by genetic recombination technology, insecticidal proteins derived from Bacillus cereus and Bacillus popilliae, insecticidal protein Vip1 derived from Bt bacteria , Vip2, Vip3, nematode-derived insecticidal protein, scorpion toxin, spider toxin, bee toxin or insect-specific neurotoxin-produced toxin, filamentous fungal toxin, plant lectin, agglutinin, trypsin inhibitor, serine Protease inhibitors, protease inhibitors such as patatin, cystatin, papain inhibitor, lysine, corn-RIP, ribosome inactivating protein (RIP) such as abrin, ruffin, saporin, bryodin, 3-hydroxysterloy Oxidase, ecdysteroid-UDP-glucosyltransferase, steroid metabolic enzymes such as cholesterol oxidase, ecdysone inhibitor, ion channel inhibitors such as HMG-CoA reductase, sodium channel, calcium channel inhibitor, juvenile hormone esterase, diuretic hormone receptor Body, stilbene synthase, bibenzyl synthase, chitinase, glucanase and the like.

In addition, transgenic plants imparted with pest resistance by introducing one or two or more insecticidal protein genes are already known, and some genetically modified plants are commercially available.
Examples of transgenic cotton imparted with pest resistance include Bollgard (registered trademark) cotton that expresses the insecticidal protein Cry1Ac derived from Bt bacteria, and Bollgard II (registered trademark) that expresses the insecticidal proteins Cry1Ac and Cry2Ab derived from Bt bacteria. ) Cotton, Bollgard III (registered trademark) expressing insecticidal proteins Cry1Ac, Cry2Ab, Vip3A derived from Bt bacteria, VIPCOT (registered trademark) expressing insecticidal proteins Vip3A and Cry1Ac derived from Bt bacteria, insecticidal properties derived from Bt bacteria Commercially available recombinant cotton with a trade name including WideStrike (registered trademark) that expresses the proteins Cry1Ac and Cry1F is commercially available.
Examples of genetically modified maize imparted with pest resistance include Yieldgard® Rootworm RW that expresses the insecticidal protein Cry3Bb1 derived from Bt bacteria, and YieldGard Plus that expresses the insecticidal proteins Cry1Ab and Cry3Bb1 derived from Bt bacteria. Trademark), insecticidal protein Cry1A. YieldGard (registered trademark) VT Pro (registered trademark) and the like that express 105 and Cry2Ab2 are commercially available. Agrisure (registered trademark) RW expressing insecticidal protein mCry3A derived from Bt bacteria, Agrisure (registered trademark) Viptera expressing insecticidal protein Vip3Aa20 derived from Bt bacteria, Agrisure expressing insecticidal protein eCry3.1 Ab derived from Bt bacteria (Registered trademark) Duracade (registered trademark) and the like are also commercially available.
As examples of genetically modified potatoes imparted with pest resistance, Atlantic NewLeaf (registered trademark) potato, NewLeaf (registered trademark) Russet Burbank poto, etc. that express the insecticidal protein Cry3A derived from Bt bacteria are commercially available.

Plants to which disease resistance has been imparted by gene recombination techniques include common bean (Phaseolus vulgaris), papaya (Carica papaya), plum (Prunus domestica), potato, and Cucurbita pepo. , Sweet pepper (Capsicum annuum), tomato and the like. As a genetically modified plant imparted with resistance to plant viral diseases, specifically, a gene set in which a gene that generates double-stranded RNA of a replica protein of Bean golden mosaic virus is introduced. Recombinant kidney beans, transgenic papaya into which a coat protein gene of Papaya ringspot virus has been introduced, a coat protein gene of Potato virus Y, or a potato leaf roll virus ( Potato leaf roll virus) Recombinant potato introduced with a replication enzyme domain gene, Cucumber mosaic virus coat protein Gene, water melon mosaic virus coat protein gene, zucchini yellow mosaic virus coat protein gene, recombinant squash, cucumber mosaic virus There are a genetically modified sweet pepper and a genetically modified tomato introduced with a coat protein gene of (Cucumber mosaic virus).
As an example of a genetically modified potato imparted with resistance to a plant viral disease, a genetically modified potato with a trade name including Newleaf (registered trademark) is commercially available.
Plants imparted with disease resistance also include plants imparted with the ability to produce anti-pathogenic substances having a selective action using genetic engineering techniques. As examples of anti-pathogenic substances, PR proteins and the like are known (PRPs, EP392225). Such anti-pathogenic substances and genetically modified plants that produce them are described in EP392225, WO199533818, EP353191, and the like. Examples of anti-pathogenic substances include, for example, ion channel inhibitors such as sodium channel inhibitors, calcium channel inhibitors (KP1, KP4, KP6 toxins produced by viruses, etc.), stilbene synthase, Microorganisms such as benzyl synthase, chitinase, glucanase, peptide antibiotics, heterocyclic antibiotics, and protein factors involved in plant disease resistance (referred to as plant disease resistance genes and described in WO2003010906) are produced. And anti-pathogenic substances.

For plants whose quality of the product has been modified by genetic recombination technology, modification of lignin production, modification of oil or fatty acid component, production of phytate degrading enzyme, modification of flower color, modification of alpha amylase activity, modification of amino acid Genetically modified plants with modified product quality such as starch or carbohydrate component modification, suppression of acrylamide production, reduction of black spots due to mechanical damage, antiallergic properties, reduction of nicotine production, aging or ripening delay, etc. It is done.
Alfalfa-derived S-adenosyl-L-methionine involved in lignin production: trans-caffeoyl CoA A gene that generates double-stranded RNA of 3-methyltransferase (ccomt) gene was introduced to reduce the lignin content by RNA interference. There is a genetically modified alfalfa.
A transgenic canola whose triacylglyceride content, including lauric acid, has been increased by introducing a 12: 0 ACP thioesterase gene derived from Laurel (Umbellaria californica) involved in fatty acid synthesis under the trade name Laurical (registered trademark) Canola. Has been developed.
A genetically modified canola that enhances the degradation of endogenous phytic acid by introducing a 3-phytase gene (phyA) derived from Aspergillus niger, a plant phytic acid degrading enzyme, is produced by Phytaseed (registered trademark) Canola. Developed under the trade name. Similarly, genetically modified maize has been developed in which degradation of endogenous phytic acid is enhanced by introducing a black mold-derived 3-phytase gene (phyA).
Dihydroflavonol-4-reductase gene from Petunia hybrida, an enzyme that produces the blue pigment delphinidin and its derivatives, and petunia, pansy (Viola wittrockiana), salvia (Salvia splendens), or flavonoids from carnation A genetically modified carnation in which the flower color is controlled to be blue by introducing a -3 ′, 5′-hydroxylase gene is known. The genetically modified carnations in which the flower color is controlled to blue are Moondust (registered trademark), Moonshadow (registered trademark), Moonshade (registered trademark), Moonlite (registered trademark), Moonaqua (registered trademark), Moonvista (registered trademark), Moonique ( It has been developed under trade names such as (registered trademark), Moonpearl (registered trademark), Moonberry (registered trademark), and Moonvelvet (registered trademark). In addition, by introducing an anthocyanin-5-acyltransferase gene derived from Torenia sp., An enzyme that produces the blue pigment delphinidin and its derivatives, and a flavonoid-3 ′, 5′-hydroxylase gene derived from pansy A genetically modified rose whose flower color is controlled to blue has also been developed.
There is a genetically modified maize that has enhanced the production of bioethanol by introducing a thermostable alpha-amylase gene (amy797E) of Thermococcales sp. For starch degradation, under the trade name of Enogen® Has been developed.
Genetically modified maize enhanced lysine production by introducing a dihydrodipicolinate synthase gene (cordapA) from Corynebacterium glutamicum for the production of lysine, an amino acid, includes Mavera® Developed under the trade name.
Genetically modified melons and genetically modified tomatoes that have improved shelf life by introducing the S-adenosylmethion hydrolase gene (sam-K) derived from Escherichia coli bacteriophage T3 relating to ethylene production of plant hormones have been developed. . In addition, a gene lacking a part of the ACC synthase gene derived from tomato involved in ethylene production of plant hormones, an ACC deaminase gene derived from Pseudomonas chlororaphis that degrades ethylene precursor ACC, and pectin on the cell wall Tomato-derived polygalacturonase gene double-stranded RNA or a tomato-derived ACC oxidase gene involved in ethylene production has been introduced to improve genetic shelf tomatoes. ing. A genetically modified tomato improved in shelf life by introducing a gene that generates double-stranded RNA of a polygalacturonase gene derived from tomato has been developed under the trade name FLAVR SAVR (registered trademark).
Genes that generate double-stranded RNA of transcription factor genes that promote starch degradation from potato, genes that generate double-stranded RNA of polyphenol oxidase gene derived from potato, and genes that are involved in asparagine production Products that include Innate (registered trademark), a genetically modified potato that reduces the possibility of starch degradation, black spot formation due to mechanical damage, and generation of carcinogenic substances (acrylamide) by heating Developed by name. In addition, a genetically modified potato having a reduced amylose content by introducing an antisense gene of starch synthase derived from potato has been developed under the trade name of Amflora (registered trademark).
A transgenic rice plant that has an immunotolerant effect and a hay fever alleviating effect has been developed by introducing an antigen protein gene (7crp) of a modified cedar pollen.
By introducing a partial gene (gm-fad2-1) of ω-6 desaturase derived from soybean, which is a fatty acid desaturase, genetically modified soybean, which suppresses the expression of the same gene and enhances the oleic acid content, (Registered trademark) or Treus (registered trademark). In addition, a gene that generates double-stranded RNA of soybean-derived acyl-acyl carrier protein thioesterase gene (fatb1-A) and a double-stranded RNA of soybean-derived δ-12 desaturase gene (fad2-1A) Genetically modified soybeans having a reduced saturated fatty acid content by introducing a gene to be produced have been developed under the trade name of Visual Gold (registered trademark). In addition, a genetically modified soybean in which the content of ω3 fatty acid is enhanced by introducing a δ-6 desaturase gene (Pj.D6D) derived from primrose and a δ-12 desaturase gene (Nc.Fad3) derived from red bread fungus has been developed. Yes.
A genetically modified tobacco having a reduced nicotine content by introducing an antisense gene of tobacco-derived quinolinate phosphoribosyltransferase gene (NtQPT1) has been developed.
A phytoene synthase gene (psy) derived from Narcissus pseudonarcissus and a carotene desaturase gene (crt1) derived from a soil bacterium (Erwinia uredovora) that synthesizes carotenoids are introduced and expressed in the endosperm tissue in a specific manner. -Golden rice, a genetically modified rice that can produce carotene and harvest rice containing vitamin A, has also been developed.

Plants whose fertility traits and the like have been modified by gene recombination techniques include genetically modified plants in which the plants are given male sterility and fertility recovery traits. There are genetically modified maize and genetically modified chicory imparted with male sterility by expressing a ribonuclease gene (barnase) derived from Bacillus amyloliquefaciens in cocoon tapetum cells. In addition, there is a genetically modified maize imparted with male sterility by introducing a DNA adenine methylase gene (dam) derived from E. coli. Further, a gene set in which fertility traits are controlled by introducing an alpha-amylase gene (zm-aa1) derived from corn that gives male sterility traits and an ms45 protein gene (ms45) derived from corn that gives fertility recovery traits There is also a replacement corn.
There is a genetically modified canola imparted with a function of restoring fertility by expressing a ribonuclease-inhibiting protein gene (barstar) derived from Bacillus bacteria in cocoon tapetum cells. Further, a gene set in which fertility traits are controlled by expressing a ribonuclease gene (barnase) derived from Bacillus that gives male sterile traits and a ribonuclease inhibitor protein gene (barstar) derived from Bacillus that gives fertility recovery traits There is also a replacement canola.

  Examples of the plant imparted with environmental stress tolerance by genetic recombination technology include a genetically modified plant imparted with drought tolerance. A drought-tolerant maize introduced with a cold shock protein gene (cspB) derived from Bacillus subtilis has been developed under the trade name of Genuity (R) DraughtGard (R). Furthermore, drought-resistant sugarcane into which a choline dehydrogenase gene (RmBetA) derived from Rhizobium meliloti or Escherichia coli has been developed has also been developed.

  Examples of plants whose growth and yield traits have been modified by genetic recombination techniques include genetically modified plants with enhanced growth ability. For example, genetically modified soybeans and the like into which a gene (bbx32) encoding a transcription factor that controls diurnal properties derived from Arabidopsis thaliana has been developed.

The plant in the present invention may be a plant modified using a technique other than the genetic recombination technique. More specifically, it may be a plant imparted with environmental stress resistance, disease resistance, herbicide resistance, pest resistance, etc. by classical breeding technology, genetic marker breeding technology, genome editing technology, or the like.
Examples of plants to which herbicide tolerance has been imparted by classical or genetic marker breeding techniques include corn, rice, wheat, sunflower (Helianthus annuus), canola, which are resistant to imidazolinone-based ALS-inhibiting herbicides such as imazetapill, Lentils (Lens culinaris) and the like are sold under the trade name of Clearfield (registered trademark). Moreover, STS soybean etc. which are sulfonylurea type | system | group herbicide tolerance soybean are examples of the plant to which tolerance to sulfonyl type | system | group ALS inhibition type herbicides, such as thifensulfuron methyl, was provided by the classic or gene marker breeding technique. Similarly, SR corn, which is cetoxydim-resistant maize, is an example of a plant to which tolerance is imparted to acetyl CoA carboxylase inhibitors such as trion oxime and aryloxyphenoxypropionic acid herbicides by classical or genetic marker breeding techniques. is there.
An example of a plant to which pest resistance is imparted by classical or genetic marker breeding techniques is soybean having a Rag1 (Resistance Aphid Gene 1) gene that is an aphid resistance gene. Moreover, as a plant imparted with nematode tolerance by a classical breeding method, soybean imparted with resistance to cyst nematode, cotton imparted with resistance to root knot nematode, and the like can be mentioned.
As a plant to which disease resistance has been imparted by classical or genetic marker breeding techniques, resistance to corn and gray leaf spot that have been imparted resistance to anthracnose disease is given. Resistant corn, corn imparted resistance to bacterial wilt disease, maize imparted resistance to Fusarium stalk rot, resistant to Asian soybean rust Soybeans, Peptotolerant to Phytophathora, Lettuce tolerant to powdery mildew, Tomato tolerant to Bacterial wilt And tomatoes with resistance to geminivirus, lettuce with resistance against downy mildew, and the like.
As an example of a plant to which drought tolerance has been imparted by classical or gene marker breeding techniques, drought-tolerant maize has been developed under the trade names of Agurisure Artesian (registered trademark) and Optimum AQUAmax (registered trademark). Also,
As an example of a plant to which herbicide resistance has been imparted by genome editing technology, a sulfonylurea herbicide is introduced by a rapid variety development technology that introduces a sulfonylurea herbicide resistance mutation into an ALS gene via a DNA and RNA chimeric oligonucleotide. A canola imparted with resistance has been developed under the trade name SU Canola®.

In addition, for the above-mentioned plants, using genetic recombination technology, classical breeding technology, genetic marker breeding, or genome editing technology, environmental stress resistance, disease resistance, herbicide resistance, pest resistance, Two or more types of properties possessed by the parental line by crossing two or more lines with growth, yield traits, product quality, fertile traits, etc., and genetically modified plants with similar or different properties The assigned line is also included. An example of such a plant is a genetically modified plant imparted with both herbicide resistance and pest resistance.
For example, as a transgenic plant imparted with glyphosate resistance and pest resistance, Round Ready (registered trademark) Bollgard (registered trademark) cotton, Round Ready (registered trademark) Bollgard II (registered trademark) cotton, Round Ready (registered trademark) Trade names of Flex (registered trademark) Bollgard II (registered trademark) cotton, Bollgard (registered trademark) III x Roundup Ready (registered trademark) Flex (registered trademark), VIPCOT (registered trademark) Roundup Ready Flex (registered trademark) Cotton, etc. Genetically modified cotton has been developed. In addition, Agurisure (registered trademark) GT / RW, Round Ready (registered trademark) YieldGuard (registered trademark) maize, Genuity (registered trademark) VT Double Pro (registered trademark), Genuity (registered trademark) VT Triple Pro (registered trademark), YieldGard (R), YieldGard (R) CB + RW, YieldGard (R) VT (R) Rootworm (R) RR2, YieldGard (R) RW + RR, YieldGard (R) VTTriGr (R) A genetically modified corn having a trade name such as Plus with RR has been developed. In addition, genetically modified soybeans such as Intatta (R) Roundup Ready (R) 2 Pro have been developed.
For example, as a genetically modified plant imparted with glufosinate resistance and pest resistance, products such as Widestrike (registered trademark) Cotton, Twinlink (registered trademark) Cotton, Fibermax (registered trademark) LibertyLink (registered trademark) Bollgard II (registered trademark) Named genetically modified cotton has been developed. Also, Agriure (registered trademark) CB / LL, Agriure (registered trademark) CB / LL / RW, Agriure (registered trademark) Viptera (registered trademark) 2100, Agriure (registered trademark) Viptera (registered trademark) 3100, Bt Xtra (registered trademark). (Trademark) Maize, NatureGard Knockout (registered trademark), Herculex (registered trademark) RW, Herculex (registered trademark) CB, Herculex (registered trademark) XTRA, Starlink (registered trademark) Maize, Liberty Link (registered trademark) YieldGard registered trademark A genetically modified corn having a trade name such as Maize has been developed.
For example, as a genetically modified plant imparted with glyphosate resistance, glufosinate resistance, and pest resistance, Widestrike (registered trademark) Roundup Ready (registered trademark) Cotton, Widestrike (registered trademark) Roundup Ready Flex (registered trademark) Cotton, Registered trademark x Round Ready Flex (registered trademark) x VIPCOT (registered trademark) Cotton, Glytol (registered trademark) x Twinlink (registered trademark) and the like have been developed. In addition, Agurisure (registered trademark) GT / CB / LL, Agurisure (registered trademark) 3000GT, Agrisure (registered trademark) 3122, Agrisure (registered trademark) Viptera (registered trademark) 3110, Agrisure (registered trademark) Viptera 3111, Registered Trademark) Viptera 3220, Agurisure (registered trademark) Duracade (registered trademark) 5122, Agrisure (registered trademark) Duracade (registered trademark) 5222, Optimum (registered trademark) Intrict, Optimum (registered trademark) TRIsect, Optimum (registered trademark) InTRtrust , Optimum (TM) Intrasect Xtreme, Genuity (R) Sma Genetic recombination of trade names such as rtStax (registered trademark), Power Core (registered trademark), Herculex (registered trademark) I RR, Herculex (registered trademark) RW Roundup Ready (registered trademark) 2, Herculex XTRA (registered trademark) RR Corn is being developed.
For example, a genetically modified cotton having a trade name such as BXN (registered trademark) Plus Bollgard (registered trademark) Cotton has been developed as a genetically modified plant imparted with bromoxynyl resistance and pest resistance.

As an example of a line provided with two or more of the above-mentioned plural traits, there is a genetically modified plant provided with disease resistance and pest resistance. For example, Hi-Lite NewLeaf (registered trademark) Y Potato, NewLeaf (registered trademark) Y Russet Burbank Potato, ShepodyNeed as a genetically modified plant imparted with resistance to potato virus Y (Potato virus Y) and pest resistance. (Trademark) Y Potato, or a genetically modified plant imparted with resistance to potato leaf roll virus and pest resistance, and a gene group with a trade name such as NewLeaf (registered trademark) Plus Russset Burbank Potato Replacement potatoes have been developed.
An example of a line provided with two or more of the above-mentioned plural traits is a genetically modified plant provided with herbicide resistance and modified product quality. For example, genetically modified canola and genetically modified maize imparted with glufosinate resistance and fertile traits have been developed under the trade names of InVigor (registered trademark) Canola and InVigor (registered trademark) Maize.
An example of a line provided with two or more of the above-mentioned plural traits is a genetically modified plant imparted with pest resistance and modified product quality. For example, genetically modified maize imparted with traits that enhance resistance to lepidopterous pests and lysine production has been developed under the trade name of Mavera (registered trademark) Yieldgard (registered trademark) Maize.
In addition, as an example of a strain provided with two or more of the above-mentioned plural traits, a genetically modified plant provided with herbicide tolerance and a modified fertility trait, a gene provided with herbicide tolerance and environmental stress tolerance Recombinant plants, genetically modified plants with herbicide resistance and modified growth and yield traits, genetically modified plants with herbicide resistance, pest resistance, and modified product quality, herbicides Genetically modified plants imparted with resistance, pest resistance, and environmental stress resistance have been developed.

Hereinafter, although this invention is demonstrated in more detail by a manufacture example, a formulation example, a test example, etc., this invention is not limited only to these examples. In the following examples, parts represent parts by weight unless otherwise specified.
First, a manufacture example is shown about manufacture of this pyridazine compound.

¹H-NMR (CDCl₃) δ: 8.28 (1H, dd), 7.90 (1H, dd), 7.58 (1H, d), 7.47 (1H, d), 7.09 (1H, d), 4.21 (3H, s). Production Example 1 (1)
17 g of 3-chloro-6-methoxypyridazine, 12 g of 2-fluoro-4- (trifluoromethyl) phenylboronic acid pinacol ester, 2.3 g of tetrakis (triphenylphosphine) palladium (0), 50 mL of 2M aqueous sodium carbonate solution and 80 mL of DME The mixture was stirred at 80 ° C. for 5 hours. Water was added to the reaction mixture allowed to cool to room temperature, extracted with ethyl acetate, and dried over anhydrous sodium sulfate. After concentration under reduced pressure, the resulting residue was subjected to silica gel column chromatography to obtain 4.81 g of intermediate (1-1) represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.28 (1H, dd), 7.90 (1H, dd), 7.58 (1H, d), 7.47 (1H, d), 7.09 (1H, d), 4.21 (3H, s ).

¹H-NMR (CDCl₃) δ: 7.72 (1H, d), 7.68-7.63 (2H, m), 7.55 (1H, d), 7.05 (1H, d), 4.21 (3H, s), 2.89 (2H, q), 1.25 (3H, t). Production Example 1 (2)
To a reaction mixture of 4.8 g of the intermediate (1-1) and 40 mL of NMP, ethanethiol 1.6 mL and sodium hydride (oil, 60%) 0.99 g were added under ice cooling, and the mixture was stirred at room temperature for 2 hours. Water was added to the reaction mixture, extracted with ethyl acetate, and dried over anhydrous sodium sulfate. The obtained organic layer was concentrated under reduced pressure to obtain an intermediate (1-2) represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 7.72 (1H, d), 7.68-7.63 (2H, m), 7.55 (1H, d), 7.05 (1H, d), 4.21 (3H, s), 2.89 (2H , q), 1.25 (3H, t).

¹H-NMR (CDCl₃) δ: 8.45 (1H, s), 8.00 (1H, d), 7.60 (1H, d), 7.53 (1H, d), 7.12 (1H, d), 4.21 (3H, s), 3.46 (2H, q), 1.29 (3H, t). Production Example 1 (3)
To a mixture of the intermediate (1-2) obtained in Production Example 1 (2) and chloroform (40 mL), 8.9 g of mCPBA (purity 65% or more) was added under ice cooling, and the mixture was stirred at room temperature for 1 day. A 10% aqueous sodium thiosulfate solution was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 3.3 g of an intermediate (1-3) represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.45 (1H, s), 8.00 (1H, d), 7.60 (1H, d), 7.53 (1H, d), 7.12 (1H, d), 4.21 (3H, s ), 3.46 (2H, q), 1.29 (3H, t).

¹H-NMR (CDCl₃) δ: 11.74 (1H, s), 8.41 (1H, s), 8.01 (1H, d), 7.62 (1H, d), 7.42 (1H, d), 7.06 (1H, d), 3.30 (2H, q), 1.30 (3H, t). Production Example 1 (4)
A mixture of 3.3 g of the intermediate (1-3) and 25 mL of concentrated hydrochloric acid was stirred for 1 hour with heating under reflux. The reaction mixture allowed to cool to room temperature was added to water, the precipitated solid was collected by filtration, and the filtrate was concentrated under reduced pressure to obtain 2.9 g of intermediate (1-4) represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 11.74 (1H, s), 8.41 (1H, s), 8.01 (1H, d), 7.62 (1H, d), 7.42 (1H, d), 7.06 (1H, d ), 3.30 (2H, q), 1.30 (3H, t).

¹H-NMR (CDCl₃) δ: 8.46 (1H, s), 8.02 (1H, d), 7.65-7.59 (2H, m), 7.27 (1H, d), 5.00 (2H, q), 3.43 (2H, q), 1.30 (3H, t).
副生成物１

¹H-NMR (CDCl₃) δ: 8.40 (1H, s), 8.02 (1H, d), 7.61 (1H, d), 7.37 (1H, d), 7.05 (1H, d), 4.81 (2H, q), 3.19 (2H, q), 1.28 (3H, t). Production Example 1 (5)
To a mixture of 0.30 g of intermediate (1-4), 0.35 g of cesium carbonate and 4 mL of NMP, 0.37 g of 2,2,2-trifluoroethyl = nonafluorobutanesulfonate was added at room temperature, and the mixture was stirred for 2 hours at room temperature. Stir. Water was added to the reaction mixture, extracted with ethyl acetate, and dried over anhydrous sodium sulfate. After concentration under reduced pressure, the resulting residue was subjected to silica gel column chromatography to obtain 0.02 g of the present pyridazine compound 1 represented by the following formula and 0.31 g of by-product 1.
The present pyridazine compound 1

¹ H-NMR (CDCl ₃ ) δ: 8.46 (1H, s), 8.02 (1H, d), 7.65-7.59 (2H, m), 7.27 (1H, d), 5.00 (2H, q), 3.43 (2H , q), 1.30 (3H, t).
By-product 1

¹ H-NMR (CDCl ₃ ) δ: 8.40 (1H, s), 8.02 (1H, d), 7.61 (1H, d), 7.37 (1H, d), 7.05 (1H, d), 4.81 (2H, q ), 3.19 (2H, q), 1.28 (3H, t).

［表１７］

本ピリダジン化合物２；¹H-NMR (CDCl₃) δ: 8.46 (1H, s), 8.02 (1H, d), 7.63 (1H, d), 7.61 (1H, d), 7.27 (1H, d), 5.08 (2H, t), 3.43 (2H, q), 1.30 (3H, t).
本ピリダジン化合物３；¹H-NMR (CDCl₃) δ: 8.46 (1H, s), 8.02 (1H, d), 7.63 (1H, d), 7.61 (1H, d), 7.24 (1H, d), 5.28-5.06 (1H, m), 5.04-4.95 (2H, m), 3.42 (2H, q), 1.30 (3H, t). Production Example 1 (6)
A compound represented by the formula R ¹ -OSO ₂ CF ₃ was used instead of 2,2,2-trifluoroethyl = nonafluorobutanesulfonate, and the following formula was produced according to the method described in Production Example 1 (5). The present pyridazine compounds represented by are shown in [Table 17].

[Table 17]

This pyridazine compound 2; ¹ H-NMR (CDCl ₃ ) δ: 8.46 (1H, s), 8.02 (1H, d), 7.63 (1H, d), 7.61 (1H, d), 7.27 (1H, d), 5.08 (2H, t), 3.43 (2H, q), 1.30 (3H, t).
The present pyridazine compound 3; ¹ H-NMR (CDCl ₃ ) δ: 8.46 (1H, s), 8.02 (1H, d), 7.63 (1H, d), 7.61 (1H, d), 7.24 (1H, d), 5.28-5.06 (1H, m), 5.04-4.95 (2H, m), 3.42 (2H, q), 1.30 (3H, t).

［表１８］

副生成物２；¹H-NMR (CDCl₃) δ: 8.40 (1H, s), 8.02 (1H, d), 7.61 (1H, d), 7.38 (1H, d), 7.04 (1H, d), 4.84 (2H, t), 3.17 (2H, q), 1.27 (3H, t).
副生成物３；¹H-NMR (CDCl₃) δ: 8.41 (1H, s), 8.02 (1H, d), 7.61 (1H, d), 7.38 (1H, d), 7.05 (1H, d), 5.18-5.01 (1H, m), 4.90-4.69 (2H, m), 3.19 (2H, q), 1.28 (3H, t). By-products represented by the following formulas generated together with the respective pyridazine compounds described in [Table 17] are shown in [Table 18].

[Table 18]

By-product 2; ¹ H-NMR (CDCl ₃ ) δ: 8.40 (1H, s), 8.02 (1H, d), 7.61 (1H, d), 7.38 (1H, d), 7.04 (1H, d), 4.84 (2H, t), 3.17 (2H, q), 1.27 (3H, t).
Byproduct 3; ¹ H-NMR (CDCl ₃ ) δ: 8.41 (1H, s), 8.02 (1H, d), 7.61 (1H, d), 7.38 (1H, d), 7.05 (1H, d), 5.18-5.01 (1H, m), 4.90-4.69 (2H, m), 3.19 (2H, q), 1.28 (3H, t).

¹H-NMR (CDCl₃) δ: 8.55 (1H, dd), 7.80 (1H, dd), 7.38 (1H, dd), 2.70 (3H, s). Production Example 2 (1)
To a mixture of 54 g of 3-chloropyridine-2-carbonitrile and 300 mL of tetrahydrofuran (hereinafter referred to as THF), 500 g of 1M methylmagnesium bromide THF solution was added dropwise under ice cooling. The reaction mixture was stirred for 2 hours under ice cooling. The obtained reaction mixture was added to 2N hydrochloric acid under ice cooling, and stirred for 30 minutes. A 1N aqueous sodium hydroxide solution was added to the mixture to adjust the pH to 8, followed by extraction with ethyl acetate. The obtained organic layer was washed with saturated brine, and then the organic layer was dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure to obtain 58 g of intermediate (4-1) represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.55 (1H, dd), 7.80 (1H, dd), 7.38 (1H, dd), 2.70 (3H, s).

¹H-NMR (CDCl₃) δ: 8.40 (1H, dd), 7.69 (1H, dd), 7.37 (1H, dd), 2.92 (2H, q), 2.72 (3H, s), 1.40 (3H, t). Production Example 2 (2)
To a suspension of 57 g of sodium hydride (oil, 60%) and 560 mL of DMF, 100 mL of ethanethiol was added dropwise under ice cooling. To the resulting mixture, a mixed solution of 204 g of intermediate (4-1) and 190 mL of DMF was added dropwise under ice cooling. The resulting reaction mixture was stirred for 1 hour under ice cooling, and then added to ice water. The precipitated solid was filtered and washed with water. The obtained solid was dissolved in ethyl acetate, and this solution was washed with saturated brine, and then the organic layer was dried over sodium sulfate. The obtained organic layer was concentrated under reduced pressure, and then the obtained solid was washed with hexane to obtain 160 g of an intermediate (4-2) represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.40 (1H, dd), 7.69 (1H, dd), 7.37 (1H, dd), 2.92 (2H, q), 2.72 (3H, s), 1.40 (3H, t ).

¹H-NMR (CDCl₃) δ: 10.60 (1H, br s), 8.43 (1H, dd), 8.13 (1H, d), 7.71 (1H, dd), 7.29 (1H, dd), 7.05 (1H, d), 2.95 (2H, q), 1.35 (3H, t). Production Example 2 (3)
To a mixture of 5.4 g of the intermediate (4-2), 2.8 g of glyoxylic acid monohydrate and 90 mL of methanol, a mixture of 2.4 g of sodium hydroxide and 60 mL of methanol solution was added dropwise under ice cooling. The reaction mixture was stirred at 60 ° C. for 2 hours. The reaction mixture was allowed to cool to room temperature, and 11 mL of acetic acid and 2.3 g of hydrazine monohydrate were sequentially added. The resulting mixture was stirred at 100 ° C. for 19 hours. The resulting mixture was allowed to cool to room temperature, saturated aqueous ammonium chloride solution was added, and the mixture was extracted with chloroform. The obtained organic layer was dried over sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 3.8 g of an intermediate (4-3) represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 10.60 (1H, br s), 8.43 (1H, dd), 8.13 (1H, d), 7.71 (1H, dd), 7.29 (1H, dd), 7.05 (1H, d), 2.95 (2H, q), 1.35 (3H, t).

¹H-NMR (CDCl₃) δ: 8.48 (1H, dd), 8.25 (1H, d), 7.79 (1H, dd), 7.63 (1H, d), 7.34 (1H, dd), 2.95 (2H, q), 1.33 (3H, t). Production Example 2 (4)
To a mixture of 2.0 g of intermediate (4-3) and 9 mL of toluene, 1 drop of DMF and 1.6 mL of phosphorus oxychloride were sequentially added at room temperature. The mixture was stirred at 100 ° C. for 2 hours. The resulting mixture was allowed to cool to room temperature and concentrated under reduced pressure. The obtained residue was diluted with chloroform, and water was added under ice cooling. The obtained mixture was extracted with chloroform, washed with water and saturated brine, and dried over sodium sulfate. The obtained organic layer was concentrated under reduced pressure to obtain 2.2 g of an intermediate (4-4) represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.48 (1H, dd), 8.25 (1H, d), 7.79 (1H, dd), 7.63 (1H, d), 7.34 (1H, dd), 2.95 (2H, q ), 1.33 (3H, t).

¹H-NMR (CDCl₃) δ: 8.93 (1H, dd), 8.54 (1H, dd), 7.95 (1H, d), 7.71 (1H, d), 7.66 (1H, dd), 3.89 (2H, q), 1.41 (3H, t). Production Example 2 (5)
To a mixture of 2.2 g of intermediate (4-4) and 43 mL of chloroform, 4.2 g of mCPBA (75%) was added under ice cooling. The reaction mixture was stirred at room temperature for 24 hours. To this mixture, 11 g of sodium sulfite and a saturated aqueous sodium hydrogen carbonate solution were added, and the mixture was extracted with chloroform. The obtained organic layer was dried over sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 2.2 g of intermediate (4-5) represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.93 (1H, dd), 8.54 (1H, dd), 7.95 (1H, d), 7.71 (1H, d), 7.66 (1H, dd), 3.89 (2H, q ), 1.41 (3H, t).

¹H-NMR (CDCl₃) δ: 8.98 (1H, dd), 8.57 (1H, dd), 8.37 (1H, d), 8.25 (1H, d), 7.72 (1H, dd), 3.90 (2H, q), 3.48 (3H, s), 1.43 (3H, t). Production Example 2 (6)
To a mixture of 3.0 g of intermediate (4-5), 880 mg of tetrabutylammonium chloride and 26 mL of DMF, 1.6 g of sodium methanesulfinate was added at room temperature. The mixture was stirred at 100 ° C. for 5 hours. The resulting mixture was allowed to cool to room temperature, added to water, and extracted with ethyl acetate. The obtained organic layer was dried over sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 3.0 g of an intermediate (4-6) represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.98 (1H, dd), 8.57 (1H, dd), 8.37 (1H, d), 8.25 (1H, d), 7.72 (1H, dd), 3.90 (2H, q ), 3.48 (3H, s), 1.43 (3H, t).

¹H-NMR (CDCl₃) δ: 8.92 (1H, dd), 8.53 (1H, dd), 7.95 (1H, d), 7.63 (1H, dd), 7.34 (1H, d), 5.28 (2H, s), 3.88 (2H, q), 1.40 (3H, t). Production Example 2 (7)
To a mixture of 0.2 g of intermediate (4-6), 0.23 g of cesium carbonate and 2 ml of NMP, 0.1 g of 2,2,2-trichloroethanol was added at room temperature, followed by 1 hour at room temperature, followed by 30 at 50 ° C. Stir for minutes. Water was added to the reaction mixture allowed to cool to room temperature, extracted with ethyl acetate, and dried over anhydrous sodium sulfate. After concentration under reduced pressure, the resulting residue was subjected to silica gel column chromatography to obtain 0.19 g of the present pyridazine compound 4 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.92 (1H, dd), 8.53 (1H, dd), 7.95 (1H, d), 7.63 (1H, dd), 7.34 (1H, d), 5.28 (2H, s ), 3.88 (2H, q), 1.40 (3H, t).

［表１９］

本ピリダジン化合物５；¹H-NMR (CDCl₃) δ: 8.92 (1H, dd), 8.53 (1H, dd), 7.94 (1H, d), 7.63 (1H, dd), 7.29 (1H, d), 5.01 (2H, q), 3.87 (2H, q), 1.40 (3H, t).
本ピリダジン化合物６；¹H-NMR (CDCl₃) δ: 8.91 (1H, dd), 8.52 (1H, dd), 7.87 (1H, d), 7.61 (1H, dd), 7.17 (1H, d), 4.83 (2H, t), 3.89 (2H, q), 2.79-2.66 (2H, m), 1.40 (3H, t).
本ピリダジン化合物１０；¹H-NMR (CDCl₃) δ: 8.91 (1H, dd), 8.52 (1H, dd), 7.86 (1H, d), 7.61 (1H, dd), 7.14 (1H, d), 4.65 (2H, t), 3.89 (2H, q), 2.42-2.28 (2H, m), 2.19-2.10 (2H, m), 1.39 (3H, t).
本ピリダジン化合物１２；¹H-NMR (CDCl₃) δ: 8.91 (1H, dd), 8.51 (1H, dd), 7.84 (1H, d), 7.60 (1H, dd), 7.13 (1H, d), 4.61 (2H, t), 3.90 (2H, q), 2.27-2.13 (2H, m), 2.00-1.92 (2H, m), 1.86-1.76 (2H, m), 1.39 (3H, t).
本ピリダジン化合物１４；¹H-NMR (CDCl₃) δ: 8.91 (1H, dd), 8.52 (1H, dd), 7.90 (1H, d), 7.62 (1H, dd), 7.20 (1H, d), 6.19 (1H, m), 3.93-3.77 (2H, m), 1.66 (3H, d), 1.39 (3H, t).
本ピリダジン化合物１５；¹H-NMR (CDCl₃) δ: 8.91 (1H, dd), 8.52 (1H, dd), 7.90 (1H, d), 7.62 (1H, dd), 7.23 (1H, d), 6.22 (1H, tt), 4.81 (2H, dt), 3.87 (2H, q), 1.40 (3H, t).
本ピリダジン化合物１６；¹H-NMR (CDCl₃) δ: 8.91 (1H, dd), 8.51 (1H, dd), 7.86 (1H, d), 7.60 (1H, dd), 7.19 (1H, d), 4.80-4.77 (2H, m), 4.08 (2H, t), 3.97 (2H, q), 3.88 (2H, q), 1.39 (3H, t).
本ピリダジン化合物１７；¹H-NMR (CDCl₃) δ: 8.92 (1H, dd), 8.53 (1H, dd), 7.94 (1H, d), 7.62 (1H, dd), 7.29 (1H, d), 5.13 (2H, t), 3.87 (2H, q), 1.40 (3H, t).
本ピリダジン化合物１８；¹H-NMR (CDCl₃) δ: 8.92 (1H, dd), 8.53 (1H, dd), 7.94 (1H, d), 7.63 (1H, dd), 7.27 (1H, d), 5.14 (2H, t), 3.87 (2H, q), 1.40 (3H, t).
本ピリダジン化合物１９；¹H-NMR (CDCl₃) δ: 8.91 (1H, dd), 8.52 (1H, dd), 7.87 (1H, d), 7.61 (1H, dd), 7.16 (1H, d), 4.92 (2H, t), 3.88 (2H, q), 2.78-2.68 (2H, m), 1.40 (3H, t).
本ピリダジン化合物２０；¹H-NMR (CDCl₃) δ: 8.92 (1H, dd), 8.53 (1H, dd), 7.94 (1H, d), 7.62 (1H, dd), 7.29 (1H, d), 5.14 (2H, t), 3.87 (2H, q), 1.40 (3H, t).
本ピリダジン化合物２１；¹H-NMR (CDCl₃) δ: 8.91 (1H, dd), 8.52 (1H, dd), 7.87 (1H, d), 7.61 (1H, dd), 7.16 (1H, d), 4.91 (2H, t), 3.88 (2H, q), 2.74 (2H, tt), 1.40 (3H, t).
本ピリダジン化合物２２；¹H-NMR (CDCl₃) δ: 8.92 (1H, dd), 8.53 (1H, dd), 8.01 (1H, d), 7.64 (1H, dd), 7.38 (1H, d), 6.86 (1H, dd), 3.82 (2H, q), 1.39 (3H, t).
本ピリダジン化合物２３；¹H-NMR (CDCl₃) δ: 8.91 (1H, dd), 8.52 (1H, dd), 7.91 (1H, t), 7.62 (1H, dd), 7.22 (1H, d), 6.12-6.03 (1H, m), 3.93-3.79 (2H, m), 1.63 (3H, d), 1.39 (3H, t).
本ピリダジン化合物２４；¹H-NMR (CDCl₃) δ: 8.91 (1H, dd), 8.52 (1H, dd), 7.90 (1H, t), 7.62 (1H, dd), 7.20 (1H, d), 6.23 (1H, m), 3.85 (2H, m), 1.67 (3H, d), 1.39 (3H, t).
本ピリダジン化合物２５；¹H-NMR (CDCl₃) δ: 8.91 (1H, dd), 8.52 (1H, dd), 7.90 (1H, d), 7.62 (1H, dd), 7.22 (1H, d), 4.89 (2H, s), 3.88 (2H, q), 1.59 (3H, d), 1.40 (3H, t).
本ピリダジン化合物２６；¹H-NMR (CDCl₃) δ: 8.91 (1H, dd), 8.52 (1H, dd), 7.91 (1H, t), 7.61 (1H, dd), 7.23 (1H, d), 6.17-6.09 (1H, m), 3.91-3.77 (2H, m), 2.12-1.88 (2H, m), 1.38 (3H, t), 1.09 (3H, t). Production Example 2 (8)
The pyridazine compound represented by the following formula produced according to the method described in Production Example 2 (7) using the compound represented by the formula R ¹ —OH in place of 2,2,2-trichloroethanol [Table 19 ].

[Table 19]

The present pyridazine compound 5; ¹ H-NMR (CDCl ₃ ) δ: 8.92 (1H, dd), 8.53 (1H, dd), 7.94 (1H, d), 7.63 (1H, dd), 7.29 (1H, d), 5.01 (2H, q), 3.87 (2H, q), 1.40 (3H, t).
This pyridazine compound 6; ¹ H-NMR (CDCl ₃ ) δ: 8.91 (1H, dd), 8.52 (1H, dd), 7.87 (1H, d), 7.61 (1H, dd), 7.17 (1H, d), 4.83 (2H, t), 3.89 (2H, q), 2.79-2.66 (2H, m), 1.40 (3H, t).
This pyridazine compound 10: ¹ H-NMR (CDCl ₃ ) δ: 8.91 (1H, dd), 8.52 (1H, dd), 7.86 (1H, d), 7.61 (1H, dd), 7.14 (1H, d), 4.65 (2H, t), 3.89 (2H, q), 2.42-2.28 (2H, m), 2.19-2.10 (2H, m), 1.39 (3H, t).
This pyridazine compound 12; ¹ H-NMR (CDCl ₃ ) δ: 8.91 (1H, dd), 8.51 (1H, dd), 7.84 (1H, d), 7.60 (1H, dd), 7.13 (1H, d), 4.61 (2H, t), 3.90 (2H, q), 2.27-2.13 (2H, m), 2.00-1.92 (2H, m), 1.86-1.76 (2H, m), 1.39 (3H, t).
This pyridazine compound 14; ¹ H-NMR (CDCl ₃ ) δ: 8.91 (1H, dd), 8.52 (1H, dd), 7.90 (1H, d), 7.62 (1H, dd), 7.20 (1H, d), 6.19 (1H, m), 3.93-3.77 (2H, m), 1.66 (3H, d), 1.39 (3H, t).
This pyridazine compound 15: ¹ H-NMR (CDCl ₃ ) δ: 8.91 (1H, dd), 8.52 (1H, dd), 7.90 (1H, d), 7.62 (1H, dd), 7.23 (1H, d), 6.22 (1H, tt), 4.81 (2H, dt), 3.87 (2H, q), 1.40 (3H, t).
This pyridazine compound 16: ¹ H-NMR (CDCl ₃ ) δ: 8.91 (1H, dd), 8.51 (1H, dd), 7.86 (1H, d), 7.60 (1H, dd), 7.19 (1H, d), 4.80-4.77 (2H, m), 4.08 (2H, t), 3.97 (2H, q), 3.88 (2H, q), 1.39 (3H, t).
This pyridazine compound 17; ¹ H-NMR (CDCl ₃ ) δ: 8.92 (1H, dd), 8.53 (1H, dd), 7.94 (1H, d), 7.62 (1H, dd), 7.29 (1H, d), 5.13 (2H, t), 3.87 (2H, q), 1.40 (3H, t).
This pyridazine compound 18; ¹ H-NMR (CDCl ₃ ) δ: 8.92 (1H, dd), 8.53 (1H, dd), 7.94 (1H, d), 7.63 (1H, dd), 7.27 (1H, d), 5.14 (2H, t), 3.87 (2H, q), 1.40 (3H, t).
The present pyridazine compound 19; ¹ H-NMR (CDCl ₃ ) δ: 8.91 (1H, dd), 8.52 (1H, dd), 7.87 (1H, d), 7.61 (1H, dd), 7.16 (1H, d), 4.92 (2H, t), 3.88 (2H, q), 2.78-2.68 (2H, m), 1.40 (3H, t).
This pyridazine compound 20: ¹ H-NMR (CDCl ₃ ) δ: 8.92 (1H, dd), 8.53 (1H, dd), 7.94 (1H, d), 7.62 (1H, dd), 7.29 (1H, d), 5.14 (2H, t), 3.87 (2H, q), 1.40 (3H, t).
The present pyridazine compound 21; ¹ H-NMR (CDCl ₃ ) δ: 8.91 (1H, dd), 8.52 (1H, dd), 7.87 (1H, d), 7.61 (1H, dd), 7.16 (1H, d), 4.91 (2H, t), 3.88 (2H, q), 2.74 (2H, tt), 1.40 (3H, t).
This pyridazine compound 22; ¹ H-NMR (CDCl ₃ ) δ: 8.92 (1H, dd), 8.53 (1H, dd), 8.01 (1H, d), 7.64 (1H, dd), 7.38 (1H, d), 6.86 (1H, dd), 3.82 (2H, q), 1.39 (3H, t).
This pyridazine compound 23; ¹ H-NMR (CDCl ₃ ) δ: 8.91 (1H, dd), 8.52 (1H, dd), 7.91 (1H, t), 7.62 (1H, dd), 7.22 (1H, d), 6.12-6.03 (1H, m), 3.93-3.79 (2H, m), 1.63 (3H, d), 1.39 (3H, t).
This pyridazine compound 24: ¹ H-NMR (CDCl ₃ ) δ: 8.91 (1H, dd), 8.52 (1H, dd), 7.90 (1H, t), 7.62 (1H, dd), 7.20 (1H, d), 6.23 (1H, m), 3.85 (2H, m), 1.67 (3H, d), 1.39 (3H, t).
This pyridazine compound 25; ¹ H-NMR (CDCl ₃ ) δ: 8.91 (1H, dd), 8.52 (1H, dd), 7.90 (1H, d), 7.62 (1H, dd), 7.22 (1H, d), 4.89 (2H, s), 3.88 (2H, q), 1.59 (3H, d), 1.40 (3H, t).
The present pyridazine compound 26; ¹ H-NMR (CDCl ₃ ) δ: 8.91 (1H, dd), 8.52 (1H, dd), 7.91 (1H, t), 7.61 (1H, dd), 7.23 (1H, d), 6.17-6.09 (1H, m), 3.91-3.77 (2H, m), 2.12-1.88 (2H, m), 1.38 (3H, t), 1.09 (3H, t).

¹H-NMR (CDCl₃) δ: 8.91 (1H, dd), 8.51 (1H, dd), 7.90 (1H, d), 7.61 (1H, dd), 7.29 (1H, d), 5.20 (2H, s), 3.85 (2H, q), 2.28 (3H, s), 1.38 (3H, t). Production Example 3 (1)
Using 1-hydroxyacetone instead of 2,2,2-trichloroethanol, an intermediate (7-1) represented by the following formula was obtained according to the method described in Production Example 2 (7).

¹ H-NMR (CDCl ₃ ) δ: 8.91 (1H, dd), 8.51 (1H, dd), 7.90 (1H, d), 7.61 (1H, dd), 7.29 (1H, d), 5.20 (2H, s ), 3.85 (2H, q), 2.28 (3H, s), 1.38 (3H, t).

¹H-NMR (CDCl₃) δ: 8.92 (1H, dd), 8.52 (1H, dd), 7.91 (1H, d), 7.62 (1H, dd), 7.25 (1H, d), 4.76 (2H, t), 3.89 (2H, q), 1.81 (3H, t), 1.40 (3H, t). Production Example 3 (2)
To a mixture of 110 mg of intermediate (7-1) and 2 mL of chloroform, 150 mg of bis (2-methoxyethyl) aminosulfur trifluoride was added dropwise under ice cooling. The mixture was stirred at room temperature for 6.5 hours. The resulting mixture was added to a saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and 3- (2,2-difluoropropoxy) -6- (3-ethanesulfonylpyridin-2-yl) pyridazine (hereinafter referred to as the present pyridazine compound 7) represented by the following formula: 31 mg was obtained.

¹ H-NMR (CDCl ₃ ) δ: 8.92 (1H, dd), 8.52 (1H, dd), 7.91 (1H, d), 7.62 (1H, dd), 7.25 (1H, d), 4.76 (2H, t ), 3.89 (2H, q), 1.81 (3H, t), 1.40 (3H, t).

¹H-NMR (CDCl₃) δ: 12.07 (1H, s), 8.90 (1H, dd), 8.49 (1H, dd), 7.80 (1H, d), 7.61 (1H, dd), 7.11 (1H, d), 3.67 (2H, q), 1.39 (3H, t). Production Example 4 (1)
Intermediate (8-1) represented by the following formula was obtained according to the method described in Production Example 2 (5) using Intermediate (4-3) instead of Intermediate (4-4).

¹ H-NMR (CDCl ₃ ) δ: 12.07 (1H, s), 8.90 (1H, dd), 8.49 (1H, dd), 7.80 (1H, d), 7.61 (1H, dd), 7.11 (1H, d ), 3.67 (2H, q), 1.39 (3H, t).

¹H-NMR (CDCl₃) δ: 8.92 (1H, dd), 8.53 (1H, dd), 7.93 (1H, d), 7.63 (1H, dd), 7.27 (1H, d), 6.21-5.90 (1H, m), 5.01 (2H, t), 3.88 (2H, q), 1.40 (3H, t).
副生成物８

¹H-NMR (CDCl₃) δ: 8.91 (1H, dd), 8.49 (1H, dd), 7.73 (1H, d), 7.63 (1H, dd), 7.10 (1H, d), 6.13-5.82 (1H, m), 4.78 (2H, t), 3.56 (2H, q), 1.38 (3H, t). Production Example 4 (2)
Intermediate (8-1) is used instead of intermediate (1-4), and 2,2,3,3,3-pentafluoro is used instead of 2,2,2-trifluoroethyl = nonafluorobutanesulfonate According to the method described in Production Example 1 (5) using propyl = trifluoromethanesulfonate, the present pyridazine compound 8 represented by the following formula and by-product 8 were obtained.

¹ H-NMR (CDCl ₃ ) δ: 8.92 (1H, dd), 8.53 (1H, dd), 7.93 (1H, d), 7.63 (1H, dd), 7.27 (1H, d), 6.21-5.90 (1H , m), 5.01 (2H, t), 3.88 (2H, q), 1.40 (3H, t).
By-product 8

¹ H-NMR (CDCl ₃ ) δ: 8.91 (1H, dd), 8.49 (1H, dd), 7.73 (1H, d), 7.63 (1H, dd), 7.10 (1H, d), 6.13-5.82 (1H , m), 4.78 (2H, t), 3.56 (2H, q), 1.38 (3H, t).

［表２０］

本ピリダジン化合物９；¹H-NMR (CDCl₃) δ: 8.92 (1H, dd), 8.53 (1H, dd), 7.94 (1H, d), 7.63 (1H, dd), 7.29 (1H, d), 5.08 (2H, t), 3.87 (2H, q), 1.40 (3H, t).
本ピリダジン化合物１１；¹H-NMR (CDCl₃) δ: 8.92 (1H, dd), 8.53 (1H, dd), 7.95 (1H, d), 7.63 (1H, dd), 7.27 (1H, d), 5.28-5.06 (1H, m), 5.05-4.96 (2H, m), 3.87 (2H, q), 1.40 (3H, t). Production Example 4 (3)
Produced according to the method described in Production Example 4 (2) using a compound represented by the formula R ¹ -OSO ₂ CF ₃ instead of 2,2,3,3,3-pentafluoropropyl = trifluoromethanesulfonate. The present pyridazine compounds represented by the following formula are shown in [Table 20].

[Table 20]

This pyridazine compound 9; ¹ H-NMR (CDCl ₃ ) δ: 8.92 (1H, dd), 8.53 (1H, dd), 7.94 (1H, d), 7.63 (1H, dd), 7.29 (1H, d), 5.08 (2H, t), 3.87 (2H, q), 1.40 (3H, t).
This pyridazine compound 11; ¹ H-NMR (CDCl ₃ ) δ: 8.92 (1H, dd), 8.53 (1H, dd), 7.95 (1H, d), 7.63 (1H, dd), 7.27 (1H, d), 5.28-5.06 (1H, m), 5.05-4.96 (2H, m), 3.87 (2H, q), 1.40 (3H, t).

［表２１］

副生成物９；¹H-NMR (CDCl₃) δ: 8.92 (1H, dd), 8.50 (1H, dd), 7.74 (1H, d), 7.64 (1H, dd), 7.10 (1H, d), 4.86 (2H, t), 3.54 (2H, q), 1.38 (3H, t).
副生成物１１；¹H-NMR (CDCl₃) δ: 8.92 (1H, dd), 8.49 (1H, dd), 7.73 (1H, d), 7.64 (1H, dd), 7.11 (1H, d), 5.21-5.00 (1H, m), 4.93-4.69 (2H, m), 3.54 (2H, q), 1.38 (3H, t). By-products represented by the following formula and produced together with the pyridazine compounds described in [Table 20] are shown in [Table 21].

[Table 21]

Byproduct 9; ¹ H-NMR (CDCl ₃ ) δ: 8.92 (1H, dd), 8.50 (1H, dd), 7.74 (1H, d), 7.64 (1H, dd), 7.10 (1H, d), 4.86 (2H, t), 3.54 (2H, q), 1.38 (3H, t).
By-product 11; ¹ H-NMR (CDCl ₃ ) δ: 8.92 (1H, dd), 8.49 (1H, dd), 7.73 (1H, d), 7.64 (1H, dd), 7.11 (1H, d), 5.21-5.00 (1H, m), 4.93-4.69 (2H, m), 3.54 (2H, q), 1.38 (3H, t).

¹H-NMR (CDCl₃) δ: 8.67 (1H, s), 7.90 (1H, s), 3.58 (3H, s), 3.41 (3H, s), 3.00 (2H, q), 1.34 (3H, t). Production Example 5 (1)
Synthesized according to the method described in International Publication No. 2013/018928, 5.0 g of 3- (ethylsulfanyl) -5- (trifluoromethyl) pyridine-2-carboxylic acid, N, O-dimethylhydroxylamine hydrochloride 1 To a mixture of .9 g and 100 mL of acetonitrile, 4.6 g of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride, 0.27 g of 1-hydroxybenzotriazole, and 5.5 mL of triethylamine were sequentially added at room temperature. . The reaction mixture was stirred at room temperature for 1 hour, water was added, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 4.8 g of an intermediate (5-1) represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.67 (1H, s), 7.90 (1H, s), 3.58 (3H, s), 3.41 (3H, s), 3.00 (2H, q), 1.34 (3H, t ).

¹H-NMR (CDCl₃) δ: 8.62 (1H, d), 7.84 (1H, d), 2.96 (2H, q), 2.74 (3H, s), 1.42 (3H, t). Production Example 5 (2)
Intermediate (5-1) represented by the following formula was obtained according to the method described in Production Example 2 (2) using Intermediate (5-1) instead of 3-chloropyridine-2-carbonitrile. .

¹ H-NMR (CDCl ₃ ) δ: 8.62 (1H, d), 7.84 (1H, d), 2.96 (2H, q), 2.74 (3H, s), 1.42 (3H, t).

¹H-NMR (CDCl₃) δ: 10.94 (1H, br s), 8.64 (1H, d), 8.21 (1H, d), 7.85 (1H, d), 7.08 (1H, d), 2.99 (2H, q), 1.39 (3H, t). Production Example 5 (3)
Intermediate (5-2) represented by the following formula was obtained according to the method described in Production Example 2 (3) using Intermediate (5-2) instead of Intermediate (4-2).

¹ H-NMR (CDCl ₃ ) δ: 10.94 (1H, br s), 8.64 (1H, d), 8.21 (1H, d), 7.85 (1H, d), 7.08 (1H, d), 2.99 (2H, q), 1.39 (3H, t).

¹H-NMR (CDCl₃) δ: 8.69 (1H, s), 8.34 (1H, d), 7.94 (1H, s), 7.68 (1H, d), 3.00 (2H, q), 1.38 (3H, t). Production Example 5 (4)
2.7 g of the intermediate (5-3) and 10 mL of phosphorus oxychloride were added, and the mixture was stirred at 100 ° C. for 6 hours. This mixture was concentrated under reduced pressure using an evaporator, and a saturated aqueous sodium hydrogen carbonate solution was added to the resulting residue under ice cooling, followed by extraction with methyl-tert-butyl ether (hereinafter referred to as MTBE). The obtained organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 1.73 g of an intermediate (5-4) represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.69 (1H, s), 8.34 (1H, d), 7.94 (1H, s), 7.68 (1H, d), 3.00 (2H, q), 1.38 (3H, t ).

¹H-NMR (CDCl₃) δ: 9.18 (1H, d), 8.78 (1H, d), 8.01 (1H, d), 7.76 (1H, d), 3.96 (2H, q), 1.45 (3H, t). Production Example 5 (5)
Intermediate (5-5) represented by the following formula was obtained according to the method described in Production Example 2 (5) using Intermediate (5-4) instead of Intermediate (4-4).

¹ H-NMR (CDCl ₃ ) δ: 9.18 (1H, d), 8.78 (1H, d), 8.01 (1H, d), 7.76 (1H, d), 3.96 (2H, q), 1.45 (3H, t ).

¹H-NMR (CDCl₃) δ: 9.16 (1H, s), 8.77 (1H, s), 8.01 (1H, d), 7.32 (1H, d), 5.10 (2H, t), 3.96 (2H, q), 1.44 (3H, t). Production Example 5 (6)
To a mixture of 0.24 g of intermediate (5-5), 0.29 g of cesium carbonate, and 3 mL of NMP, 0.10 mL of 2,2,3,3,3-pentafluoropropanol was added at room temperature. The reaction mixture was stirred at 60 ° C. for 1 hour. The resulting mixture was allowed to cool to room temperature, water was added, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain the pyridazine compound 28 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 9.16 (1H, s), 8.77 (1H, s), 8.01 (1H, d), 7.32 (1H, d), 5.10 (2H, t), 3.96 (2H, q ), 1.44 (3H, t).

本ピリダジン化合物３１；¹H-NMR (CDCl₃) δ: 9.16 (1H, s), 8.77 (1H, s), 8.00 (1H, d), 7.30 (1H, d), 6.18-5.93 (1H, m), 5.03 (2H, t), 3.96 (2H, q), 1.44 (3H, t).
本ピリダジン化合物３２；¹H-NMR (CDCl₃) δ: 8.68 (1H, s), 8.39 (1H, d), 7.92 (1H, s), 7.24 (1H, s), 5.07 (3H, m 4.15-4.08 (1H, q), 1.39 (3H, t). Production Example 5 (7)
The present pyridazine compound represented by the following formula, which was prepared according to the method described in Preparation Example 5 (6) using a compound represented by the formula R ¹ —OH instead of 2,2,3,3,3-pentafluoropropanol Is shown in [Table 22].
[Table 22]

This pyridazine compound 31; ¹ H-NMR (CDCl ₃ ) δ: 9.16 (1H, s), 8.77 (1H, s), 8.00 (1H, d), 7.30 (1H, d), 6.18-5.93 (1H, m ), 5.03 (2H, t), 3.96 (2H, q), 1.44 (3H, t).
This pyridazine compound 32; ¹ H-NMR (CDCl ₃ ) δ: 8.68 (1H, s), 8.39 (1H, d), 7.92 (1H, s), 7.24 (1H, s), 5.07 (3H, m 4.15- 4.08 (1H, q), 1.39 (3H, t).

¹H-NMR (CDCl₃) δ: 8.68 (1H, d), 8.40 (1H, d), 7.93 (1H, d), 7.28 (1H, d), 5.17-5.11 (2H, m), 3.01 (2H, q), 1.39 (3H, t). Production Example 6
This pyridazine compound 39 represented by the following formula was obtained according to the method described in Production Example 5 (6) using Intermediate (5-4) instead of Intermediate (5-5).

¹ H-NMR (CDCl ₃ ) δ: 8.68 (1H, d), 8.40 (1H, d), 7.93 (1H, d), 7.28 (1H, d), 5.17-5.11 (2H, m), 3.01 (2H , q), 1.39 (3H, t).

¹H-NMR (CDCl₃) δ: 8.68 (1H, d), 8.38 (1H, d), 7.92 (1H, d), 7.25 (1H, d), 6.05 (1H, tt), 5.10-5.03 (2H, m), 3.01 (2H, q), 1.39 (3H, t). Production Example 7
The intermediate (5-4) is used instead of the intermediate (5-5), 2,2,3,3-tetrafluoropropanol is used instead of 2,2,3,3,3-pentafluoropropanol, This pyridazine compound 40 represented by the following formula was obtained according to the method described in Production Example 5 (6).

¹ H-NMR (CDCl ₃ ) δ: 8.68 (1H, d), 8.38 (1H, d), 7.92 (1H, d), 7.25 (1H, d), 6.05 (1H, tt), 5.10-5.03 (2H , m), 3.01 (2H, q), 1.39 (3H, t).

¹H-NMR (CDCl₃) δ: 8.46 (1H, dd), 8.32 (1H, d), 7.78 (1H, dd), 7.32 (1H, dd), 7.24 (1H, d), 5.12 (2H, t), 2.96 (2H, q), 1.35 (3H, t). Production Example 8
This pyridazine compound 27 represented by the following formula was obtained according to the method described in Production Example 5 (6) using Intermediate (4-4) instead of Intermediate (5-5).

¹ H-NMR (CDCl ₃ ) δ: 8.46 (1H, dd), 8.32 (1H, d), 7.78 (1H, dd), 7.32 (1H, dd), 7.24 (1H, d), 5.12 (2H, t ), 2.96 (2H, q), 1.35 (3H, t).

¹H-NMR (CDCl₃) δ: 8.78 (1H, dd), 8.68 (1H, dd), 8.60 (1H, d), 7.64 (1H, dd), 7.30 (1H, d), 5.21-5.02 (2H, m), 3.54-3.42 (1H, m), 3.06-2.95 (1H, m), 1.41 (3H, t). Production Example 9
To a mixture of 790 mg of the pyridazine compound 27 and 7 mL of chloroform, 510 mg of 75% mCPBA was added under ice cooling. The mixture was stirred for 0.5 hour under ice cooling. A saturated aqueous sodium hydrogen carbonate solution was added to the resulting reaction mixture, and the mixture was extracted with chloroform. The obtained organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 780 mg of the pyridazine compound 29 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.78 (1H, dd), 8.68 (1H, dd), 8.60 (1H, d), 7.64 (1H, dd), 7.30 (1H, d), 5.21-5.02 (2H , m), 3.54-3.42 (1H, m), 3.06-2.95 (1H, m), 1.41 (3H, t).

¹H-NMR (CDCl₃) δ: 8.94 (1H, dd), 8.48 (1H, dd), 7.65 (1H, dd), 7.10 (1H, m), 5.03 (2H, dt), 3.46 (2H, q), 2.22 (3H, t), 1.31 (3H, t). Production Example 10
A mixture of 0.45 g of the present pyridazine compound 43 described in Production Example 16 (6), 50 mg of palladium carbon, 0.66 g of ammonium formate, and 3 mL of methanol was stirred at room temperature for 10 minutes. The mixture was heated to 60 ° C. and stirred for 2 hours. The resulting mixture was allowed to cool to room temperature, water was added, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 200 mg of the pyridazine compound 30 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.94 (1H, dd), 8.48 (1H, dd), 7.65 (1H, dd), 7.10 (1H, m), 5.03 (2H, dt), 3.46 (2H, q ), 2.22 (3H, t), 1.31 (3H, t).

¹H-NMR (CDCl₃) δ: 8.41 (1H, dd), 7.69 (1H, dd), 7.40 (1H, dd), 4.56 (1H, br s), 4.45-4.32 (2H, m), 4.16-4.08 (2H, m), 2.92 (2H, q), 1.39 (3H, t), 1.30 (3H, t). Production Example 11 (1)
A solution of 0.50 g of intermediate (4-2) and 3 mL of THF was cooled to −78 ° C., and 2.7 mL of lithium diisopropylamide (1.1 M THF solution) was added dropwise. After stirring for 1 hour, 0.53 mL of ethyl trifluoropyruvate was added and stirred for 30 minutes. To the obtained reaction mixture, a saturated aqueous ammonium chloride solution was added at room temperature, and the mixture was extracted with MTBE. The obtained organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.74 g of an intermediate (11-1) represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.41 (1H, dd), 7.69 (1H, dd), 7.40 (1H, dd), 4.56 (1H, br s), 4.45-4.32 (2H, m), 4.16- 4.08 (2H, m), 2.92 (2H, q), 1.39 (3H, t), 1.30 (3H, t).

¹H-NMR (CDCl₃) δ: 10.71 (1H, s), 8.55 (1H, s), 8.45 (1H, dd), 7.74 (1H, dd), 7.33 (1H, dd), 2.97 (2H, q), 1.37 (3H, t). Production Example 11 (2)
0.10 mL of 12N hydrochloric acid and 0.21 mL of hydrazine monohydrate were added dropwise to a solution of 0.74 g of the intermediate (11-1) and 10 mL of ethanol. After stirring at 80 ° C. for 10 hours, the mixture was concentrated under reduced pressure using an evaporator. The obtained residue was subjected to silica gel chromatography to obtain 0.25 g of an intermediate (11-2) represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 10.71 (1H, s), 8.55 (1H, s), 8.45 (1H, dd), 7.74 (1H, dd), 7.33 (1H, dd), 2.97 (2H, q ), 1.37 (3H, t).

¹H-NMR (CDCl₃) δ: 8.65 (1H, s), 8.51 (1H, dd), 7.83 (1H, dd), 7.39 (1H, dd), 2.99 (2H, q), 1.35 (3H, t). Production Example 11 (3)
Intermediate (11-3) represented by the following formula was obtained according to the method described in Production Example 5 (4) using Intermediate (11-2) instead of Intermediate (5-3).

¹ H-NMR (CDCl ₃ ) δ: 8.65 (1H, s), 8.51 (1H, dd), 7.83 (1H, dd), 7.39 (1H, dd), 2.99 (2H, q), 1.35 (3H, t ).

¹H-NMR (CDCl₃) δ: 8.95 (1H, dd), 8.56 (1H, dd), 8.22 (1H, s), 7.70-7.66 (1H, m), 5.21-5.15 (2H, m), 3.88 (2H, q), 1.43 (3H, dt). Production Example 11 (4)
0.12 mL of 2,2,3,3,3-pentafluoropropanol and 0.36 g of cesium carbonate were added to a solution of 0.26 g of intermediate (11-3) and NMP 3 mL, heated to 70 ° C., and stirred for 2 hours. . To the obtained reaction mixture, a saturated aqueous ammonium chloride solution was added at room temperature, and the mixture was extracted with MTBE. The obtained organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was dissolved in 5 mL of chloroform, and 0.41 g of 75% mCPBA was added under ice cooling, followed by stirring for 1 hour. To the obtained reaction mixture, a saturated aqueous sodium hydrogencarbonate solution and an aqueous sodium thiosulfate solution were added at room temperature, and the mixture was extracted with chloroform. The obtained organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.20 g of the pyridazine compound 34 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.95 (1H, dd), 8.56 (1H, dd), 8.22 (1H, s), 7.70-7.66 (1H, m), 5.21-5.15 (2H, m), 3.88 (2H, q), 1.43 (3H, dt).

¹H-NMR (CDCl₃) δ: 8.96-8.94 (1H, m), 8.56 (1H, dd), 8.21 (1H, s), 7.67 (1H, dd), 6.19-5.91 (1H, m), 5.11 (2H, t), 3.93-3.85 (2H, m), 1.43 (3H, t). Production Example 12
According to the method described in Production Example 11 (4), using 2,2,3,3-tetrafluoropropanol instead of 2,2,3,3,3-pentafluoropropanol, the following formula Pyridazine compound 33 was obtained.

¹ H-NMR (CDCl ₃ ) δ: 8.96-8.94 (1H, m), 8.56 (1H, dd), 8.21 (1H, s), 7.67 (1H, dd), 6.19-5.91 (1H, m), 5.11 (2H, t), 3.93-3.85 (2H, m), 1.43 (3H, t).

¹H-NMR (CDCl₃) δ: 8.40 (1H, dd), 7.69 (1H, dd), 7.38 (1H, dd), 4.29 (1H, s), 4.23 (2H, q), 3.86 (1H, d), 3.61 (1H, d), 2.91 (2H, q), 1.52 (3H, s), 1.39 (3H, t), 1.30-1.22 (3H, m).製造例１３（２） Production Example 13 (1)
Intermediate (13-1) represented by the following formula was obtained according to the method described in Production Example 11 (1) using ethyl pyruvate instead of ethyl trifluoropyruvate.

¹ H-NMR (CDCl ₃ ) δ: 8.40 (1H, dd), 7.69 (1H, dd), 7.38 (1H, dd), 4.29 (1H, s), 4.23 (2H, q), 3.86 (1H, d ), 3.61 (1H, d), 2.91 (2H, q), 1.52 (3H, s), 1.39 (3H, t), 1.30-1.22 (3H, m). Production Example 13 (2)

¹H-NMR (CDCl₃) δ: 10.70 (1H, s), 8.43 (1H, dd), 7.93 (1H, q), 7.71 (1H, dd), 7.28 (1H, dd), 2.94 (2H, q), 2.29 (3H, d), 1.34 (3H, t). Production Example 13 (2)
The intermediate (13-2) represented by the following formula was obtained according to the method described in Production Example 11 (2) using the intermediate (13-1) instead of the intermediate (11-1).

¹ H-NMR (CDCl ₃ ) δ: 10.70 (1H, s), 8.43 (1H, dd), 7.93 (1H, q), 7.71 (1H, dd), 7.28 (1H, dd), 2.94 (2H, q ), 2.29 (3H, d), 1.34 (3H, t).

¹H-NMR (CDCl₃) δ: 8.47 (1H, dd), 8.10 (1H, d), 7.79 (1H, dd), 7.33 (1H, dd), 2.95 (2H, q), 2.49 (3H, d), 1.33 (3H, t). Production Example 13 (3)
2.0 g of the intermediate (13-2), 9 mL of phosphorus oxychloride, and 30 mL of toluene were added and stirred at 100 ° C. for 4 hours. The mixture is concentrated under reduced pressure using an evaporator, and a saturated aqueous sodium hydrogen carbonate solution is added to the resulting residue under ice cooling, followed by extraction with MTBE. The obtained organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 1.9 g of an intermediate (13-3) represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.47 (1H, dd), 8.10 (1H, d), 7.79 (1H, dd), 7.33 (1H, dd), 2.95 (2H, q), 2.49 (3H, d ), 1.33 (3H, t).

¹H-NMR (CDCl₃) δ: 8.45 (1H, dd), 8.08 (1H, d), 7.77 (1H, dd), 7.31 (1H, dd), 6.03 (1H, tt), 5.04 (2H, ddd), 2.95 (2H, q), 2.34 (3H, d), 1.34 (3H, t).
本ピリダジン化合物３５

¹H-NMR (CDCl₃) δ: 8.91 (1H, s), 8.52 (1H, dd), 7.73 (1H, s), 7.62 (1H, dd), 6.03 (1H, tt), 5.00 (2H, t), 3.89 (2H, q), 2.35 (3H, d), 1.40 (3H, t). Production Example 13 (4)
To a solution of 0.92 g of intermediate (13-3) and NMP 5 mL, 2,6,3,3-tetrafluoropropanol 0.46 mL and cesium carbonate 1.57 g were added, heated to 70 ° C. and stirred for 4 hours. To the obtained reaction mixture, a saturated aqueous ammonium chloride solution was added at room temperature, and the mixture was extracted with MTBE. The obtained organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was dissolved in 20 mL of chloroform, 1.7 g of mCPBA was added under ice cooling, and the mixture was stirred for 1 hour. To the obtained reaction mixture, a saturated aqueous sodium hydrogencarbonate solution and an aqueous sodium thiosulfate solution were added at room temperature, and the mixture was extracted with chloroform. The obtained organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.25 g of the present pyridazine compound 37 and 0.73 g of the present pyridazine compound 35 represented by the following formula.
The present pyridazine compound 37

¹ H-NMR (CDCl ₃ ) δ: 8.45 (1H, dd), 8.08 (1H, d), 7.77 (1H, dd), 7.31 (1H, dd), 6.03 (1H, tt), 5.04 (2H, ddd ), 2.95 (2H, q), 2.34 (3H, d), 1.34 (3H, t).
The present pyridazine compound 35

¹ H-NMR (CDCl ₃ ) δ: 8.91 (1H, s), 8.52 (1H, dd), 7.73 (1H, s), 7.62 (1H, dd), 6.03 (1H, tt), 5.00 (2H, t ), 3.89 (2H, q), 2.35 (3H, d), 1.40 (3H, t).

¹H-NMR (CDCl₃) δ: 8.45 (1H, dd), 8.09 (1H, d), 7.77 (1H, dd), 7.31 (1H, dd), 5.11 (2H, td), 2.95 (2H, q), 2.35 (3H, d), 1.34 (3H, t).
本ピリダジン化合物３６

¹H-NMR (CDCl₃) δ: 8.91 (1H, dd), 8.52 (1H, dd), 7.74 (1H, s), 7.62 (1H, dd), 5.06 (2H, t), 3.89 (2H, q), 2.35 (3H, s), 1.40 (3H, t). Production Example 14
In place of 2,2,3,3-tetrafluoropropanol, 2,2,3,3,3-pentafluoropropanol is used, and is represented by the following formula according to the method described in Production Example 13 (4). This pyridazine compound 38 and this pyridazine compound 36 were obtained.
The present pyridazine compound 38

¹ H-NMR (CDCl ₃ ) δ: 8.45 (1H, dd), 8.09 (1H, d), 7.77 (1H, dd), 7.31 (1H, dd), 5.11 (2H, td), 2.95 (2H, q ), 2.35 (3H, d), 1.34 (3H, t).
The present pyridazine compound 36

¹ H-NMR (CDCl ₃ ) δ: 8.91 (1H, dd), 8.52 (1H, dd), 7.74 (1H, s), 7.62 (1H, dd), 5.06 (2H, t), 3.89 (2H, q ), 2.35 (3H, s), 1.40 (3H, t).

¹H-NMR (CDCl₃) δ: 8.94 (1H, dd), 8.39 (1H, dd), 7.73 (1H, d), 7.67 (1H, dd), 6.95 (1H, d), 4.99-4.76 (2H, m), 3.64-3.50 (2H, m), 1.39 (3H, t).
本ピリダジン化合物４２

¹H-NMR (CDCl₃) δ: 8.50 (1H, dd), 7.91 (1H, dd), 7.74 (1H, d), 7.61 (1H, dd), 6.96 (1H, d), 4.86 (2H, t), 3.30-3.24 (2H, m), 1.31 (3H, t). Production Example 15
To a solution of 500 mg of the present pyridazine compound 9 and chloroform 2.5 mL, 610 mg of 75% mCPBA was added under ice cooling and stirred for 24 hours. To the obtained reaction mixture, a saturated aqueous sodium hydrogen carbonate solution and an aqueous sodium sulfite solution were added at room temperature, and the mixture was extracted with chloroform. The obtained organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 230 mg of the present pyridazine compound 41 and 300 mg of the present pyridazine compound 42 represented by the following formula.
The present pyridazine compound 41

¹ H-NMR (CDCl ₃ ) δ: 8.94 (1H, dd), 8.39 (1H, dd), 7.73 (1H, d), 7.67 (1H, dd), 6.95 (1H, d), 4.99-4.76 (2H , m), 3.64-3.50 (2H, m), 1.39 (3H, t).
The present pyridazine compound 42

¹ H-NMR (CDCl ₃ ) δ: 8.50 (1H, dd), 7.91 (1H, dd), 7.74 (1H, d), 7.61 (1H, dd), 6.96 (1H, d), 4.86 (2H, t ), 3.30-3.24 (2H, m), 1.31 (3H, t).

¹H-NMR (CDCl₃) δ: 8.39 (1H, dd), 7.69 (1H, dd), 7.36 (1H, dd), 3.22 (2H, q), 2.92 (2H, q), 1.39 (3H, t), 1.21 (3H, t). Production Example 16 (1)
In accordance with the method described in Production Example 2 (2), using 1- (3-chloropyridin-2-yl) propan-1-one instead of the intermediate (4-1), an intermediate represented by the following formula A body (16-1) was obtained.

¹ H-NMR (CDCl ₃ ) δ: 8.39 (1H, dd), 7.69 (1H, dd), 7.36 (1H, dd), 3.22 (2H, q), 2.92 (2H, q), 1.39 (3H, t ), 1.21 (3H, t).

¹H-NMR (CDCl₃) δ: 8.46 (1H, dd), 7.78 (1H, dd), 7.38 (1H, dd), 6.19 (1H, q), 2.93 (2H, q), 2.43 (3H, d), 1.33 (3H, t). Production Example 16 (2)
Under ice-cooling, 1.41 g of glyoxylic acid monohydrate was added to 12 mL of 2N sodium hydroxide, and the mixture was stirred for 10 minutes. Thereafter, 12 mL of methanol and 1.5 g of the intermediate (16-1) were added to the reaction solution, followed by stirring for 1 hour. 12N hydrochloric acid was added to this reaction solution, and the mixture was stirred for 1 hour. The obtained solid was filtered and dried to obtain 1.3 g of an intermediate (16-2) represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.46 (1H, dd), 7.78 (1H, dd), 7.38 (1H, dd), 6.19 (1H, q), 2.93 (2H, q), 2.43 (3H, d ), 1.33 (3H, t).

¹H-NMR (CDCl₃) δ: 8.48 (1H, dt), 7.74 (1H, d), 7.33 (1H, ddd), 6.86 (1H, t), 2.89 (2H, q), 2.06 (3H, br s), 1.28 (3H, t). Production Example 16 (3)
0.06 g of sodium sulfite was added to a solution of 0.10 g of the intermediate (16-2) and water 3 mL, and the mixture was stirred at 60 ° C. for 1 hour. To this reaction mixture, 1 mL of 12N hydrochloric acid and 0.05 mL of hydrazine monohydrate were added to reach 90 ° C. After stirring for 4 hours, the mixture was slowly stirred under ice-cooling, and the resulting crystals were filtered and dried to obtain 84 mg of an intermediate (16-3) represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.48 (1H, dt), 7.74 (1H, d), 7.33 (1H, ddd), 6.86 (1H, t), 2.89 (2H, q), 2.06 (3H, br s), 1.28 (3H, t).

¹H-NMR (CDCl₃) δ: 8.95 (1H, dd), 8.50 (1H, dd), 7.68 (1H, dd), 7.52 (1H, d), 3.48 (2H, q), 2.24 (3H, s), 1.31 (3H, t). Production Example 16 (4)
Intermediate (16-3) represented by the following formula was obtained according to the method described in Production Example 5 (4) using Intermediate (16-3) instead of Intermediate (5-3).
Intermediate (16-4)

¹ H-NMR (CDCl ₃ ) δ: 8.95 (1H, dd), 8.50 (1H, dd), 7.68 (1H, dd), 7.52 (1H, d), 3.48 (2H, q), 2.24 (3H, s ), 1.31 (3H, t).

¹H-NMR (CDCl₃) δ: 9.00 (1H, dd), 8.43 (1H, dd), 7.69 (1H, dd), 7.17 (1H, d), 3.52-3.33 (2H, m), 2.10 (3H, d), 1.31 (3H, t). Production Example 16 (5)
To a solution of 5.7 g of intermediate (16-4) and chloroform (150 mL), 11 g of mCPBA was added under ice cooling, and the mixture was stirred for 1 hour. To the obtained reaction mixture, a saturated aqueous sodium hydrogencarbonate solution and an aqueous sodium thiosulfate solution were added at room temperature, and the mixture was extracted with chloroform. The obtained organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 2.3 g of an intermediate (16-5) represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 9.00 (1H, dd), 8.43 (1H, dd), 7.69 (1H, dd), 7.17 (1H, d), 3.52-3.33 (2H, m), 2.10 (3H , d), 1.31 (3H, t).

¹H-NMR (CDCl₃) δ: 9.00 (1H, dd), 8.43 (1H, dd), 7.70-7.66 (1H, m), 6.82 (1H, s), 4.94-4.75 (2H, m), 3.44 (2H, m), 2.08 (3H, s), 1.31 (3H, t). Production Example 16 (6)
This pyridazine compound 43 represented by the following formula was obtained according to the method described in Production Example 5 (6) using Intermediate (16-5) instead of Intermediate (5-5).

¹ H-NMR (CDCl ₃ ) δ: 9.00 (1H, dd), 8.43 (1H, dd), 7.70-7.66 (1H, m), 6.82 (1H, s), 4.94-4.75 (2H, m), 3.44 (2H, m), 2.08 (3H, s), 1.31 (3H, t).

¹H-NMR (CDCl₃) δ: 9.18 (1H, d), 8.60 (1H, d), 7.74 (1H, d), 6.99 (1H, d), 4.98-4.79 (2H, m), 3.63 (2H, m), 1.42 (3H, t). Production Example 17
The pyridazine compound 44 represented by the following formula was obtained according to the method described in Production Example 16 (5) using the pyridazine compound 28 instead of the intermediate (16-4).

¹ H-NMR (CDCl ₃ ) δ: 9.18 (1H, d), 8.60 (1H, d), 7.74 (1H, d), 6.99 (1H, d), 4.98-4.79 (2H, m), 3.63 (2H , m), 1.42 (3H, t).

¹H-NMR (CDCl₃) δ: 9.18 (1H, d), 8.60 (1H, d), 7.73 (1H, d), 6.96 (1H, d), 6.13-5.87 (1H, m), 4.83 (2H, dd), 3.63 (2H, td), 1.42 (3H, t). Production Example 18
This pyridazine compound 45 represented by the following formula was obtained according to the method described in Production Example 16 (5) using this pyridazine compound 31 instead of the intermediate (16-4).

¹ H-NMR (CDCl ₃ ) δ: 9.18 (1H, d), 8.60 (1H, d), 7.73 (1H, d), 6.96 (1H, d), 6.13-5.87 (1H, m), 4.83 (2H , dd), 3.63 (2H, td), 1.42 (3H, t).

Next, specific compositions of the composition of the present invention will be described below.
In addition, the composition which has the combination as described in [Table A] is attached | subjected and numbered as described in [Table A]. For example, the composition of No. 1 in [Table A] is referred to as the present composition 1.
In [Table A], * described in the column of component 1 represents any one of the present pyridazine compounds 1 to 45, and the numbers described in [] in the column of each component are the numbers in the present invention. The amount (part) of each component relative to 100 parts of the composition is meant. “Β2” represents the bactericidal compound β2.

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[Table A]

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The present compositions 841-1680
In each of the present compositions 1 to 840 described in [Table A], a composition using 2 parts of tebuconazole instead of 2 parts of metconazole.

The present composition 1681-2520
In each of the present compositions 1 to 840 described in [Table A], a composition using 2 parts of difenoconazole instead of 2 parts of metconazole.

This composition 2521-360
In each of the present compositions 1 to 840 described in [Table A], a composition using 2 parts of triticonazole instead of 2 parts of metconazole.

The present composition 3361-4200
In each of the present compositions 1 to 840 described in [Table A], a composition using 2 parts of prothioconazole instead of 2 parts of metconazole.

This composition 4201-5040
In each of the present compositions 1 to 840 described in [Table A], a composition using 2 parts of diniconazole instead of 2 parts of metconazole.

This composition 5041-5880
In each of the present compositions 1 to 840 described in [Table A], a composition using 2 parts of diniconazole M instead of 2 parts of metconazole.

The present composition 5881-6720
In each of the present compositions 1 to 840 described in [Table A], a composition using 2 parts of ipconazole instead of 2 parts of metconazole.

The present composition 6721-7560
In each of the present compositions 1 to 840 described in [Table A], a composition using 2 parts of prochloraz instead of 2 parts of metconazole.

The present composition 7561-8400
In each of the present compositions 1 to 840 described in [Table A], a composition using 2 parts of fluquinconazole instead of 2 parts of metconazole.

This composition 8401-9240
In each of the present compositions 1 to 840 described in [Table A], a composition using 2 parts of triazimenol instead of 2 parts of metconazole.

The present compositions A1 to A9240
A composition further comprising 10 parts of clothianidin and 10 parts of chlorantraniliprole in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)

This composition B1-B9240
A composition further comprising 10 parts clothianidin and 10 parts cyantraniliprole in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)

This composition C1-C9240
A composition further comprising 10 parts clothianidin and 10 parts fipronil in each combination of the present compositions 1-9240 (provided that the composition is 100 parts)

This composition D1-D9240
A composition further containing 10 parts imidacloprid and 10 parts chlorantraniliprol in each combination of the present compositions 1-9240 (provided that the composition is 100 parts)

This composition E1-E9240
A composition further comprising 10 parts imidacloprid and 10 parts cyantraniliprole in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)

This composition F1-F9240
A composition further comprising 10 parts imidacloprid and 10 parts fipronil in each combination of the present compositions 1-9240 (provided that the composition is 100 parts)

This composition G1-G9240
A composition further comprising 10 parts thiamethoxam and 10 parts chlorantraniliprole in each combination of the present compositions 1-9240 (provided that the composition is 100 parts)

  A composition further containing 10 parts thiamethoxam and 10 parts cyantraniliprole in each combination of the present compositions 1-9240 (provided that the composition is 100 parts)

The present compositions I1-I9240
A composition further comprising 10 parts thiamethoxam and 10 parts fipronil in each combination of the present compositions 1-9240 (provided that the composition is 100 parts)

This composition J1-J9240
A composition comprising 10 parts of thiacloprid and 10 parts of chlorantraniliprol in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)

This composition K1-K9240
A composition further comprising 10 parts thiacloprid and 10 parts cyantraniliprole in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)

This composition L1-L9240
A composition further comprising 10 parts of thiacloprid and 10 parts of fipronil in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)

This composition M1-M9240
A composition further comprising 10 parts of furpyradiflon and 10 parts of chlorantraniliprole in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)

This composition N1-N9240
A composition further comprising 10 parts of furpyraziflon and 10 parts of cyantraniliprole in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)

This composition O1-O9240
A composition further comprising 10 parts of furpyraziflon and 10 parts of fipronil in each combination of the present compositions 1-9240 (provided that the composition is 100 parts)

This composition P1-P9240
A composition further comprising clothianidin 20 parts in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)

This composition Q1-Q9240
A composition further comprising 10 parts of insecticidal compound α and 10 parts of chlorantraniliprole in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)

This composition R1-R9240
A composition further comprising 10 parts of the insecticidal compound α and 10 parts of cyantranylprolol in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)

This composition S1-S9240
A composition further comprising 10 parts of insecticidal compound α and 10 parts of fipronil in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)

Next, formulation examples are shown.

Formulation Example 1
1 part of the present pyridazine compounds 1 to 45, 10 parts of clothianidin, 35 parts of a mixture of white carbon and polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio 1: 1), and water are mixed to make 100 parts in total. Then, each preparation is obtained by fine pulverization by a wet pulverization method.

Formulation Example 2
Of these pyridazine compounds 1-45, 10 parts of cloth, 10 parts of clothianidin, 3 parts of calcium lignin sulfonate, 2 parts of sodium lauryl sulfate, and 75 parts of synthetic hydrous silicon oxide were pulverized and mixed well. Get the agent.

Formulation Example 3
1 part of the present pyridazine compounds 1 to 45, 0.5 part of clothianidin, 1 part of synthetic hydrous silicon oxide fine powder, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65.5 parts of kaolin clay are mixed. . Next, an appropriate amount of water is added to the mixture, and the mixture is further stirred, granulated by a granulator, and dried by ventilation to obtain each granule.
Formulation Example 4
One part of the present pyridazine compounds 1 to 45, 10 parts of clothianidin, 2 parts of clothianidin, 1.5 parts of sorbitan trioleate, and 28 parts of an aqueous solution containing 2 parts of polyvinyl alcohol were mixed and pulverized by a wet pulverization method. An aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is added to make the total amount 90 parts, and further 10 parts of propylene glycol is added and stirred and mixed to obtain each preparation.

Formulation Examples 5-73
In Formulation Example 1, in place of 10 parts of clothianidin, the same operations as in Formulation Example 1 were carried out except that the present compounds and amounts used described in [Table i] were used to obtain respective formulations.
[Table i]

[Continuation of Table i]

Formulation Examples 74-142
In Formulation Example 2, in place of 10 parts of clothianidin, the same operations as in Formulation Example 2 are carried out except that the present compounds and amounts used in [Table ii] are used to obtain respective formulations.

[Table ii]

[Continuation of Table ii]

Formulation Examples 143 to 211
In Formulation Example 3, in place of 0.5 part of clothianidin, the same operations as in Formulation Example 3 were carried out except that the present compounds and amounts used described in [Table iii] were used to obtain respective formulations.

[Table iii]

[Continuation of Table iii]

Formulation Examples 212-241
In Formulation Example 4, in place of 2 parts of clothianidin, the same operation as in Formulation Example 4 is carried out except that the present compound and the amount used described in [Table iv] are used to obtain each formulation.

[Table iv]

Formulation Example 242
After mixing 10 parts of the present pyridazine compounds 1 to 45, 0.1 part of tebuconazole, 1.5 parts of sorbitan trioleate, and 28 parts of an aqueous solution containing 2 parts of polyvinyl alcohol, and then pulverizing them by a wet pulverization method Into this, an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is added to make a total amount of 90 parts, and further 10 parts of propylene glycol is added and stirred and mixed to obtain each preparation.

Formulation Examples 243 to 280
In Formulation Example 242, the same procedure as in Formulation Example 242 was performed except that 0.1 part of tebuconazole was used and the present compound and the amount used described in [Table v] were used to obtain each formulation.

[Table v]

Formulation Example 281
The present compositions 1-9240, A1 to be obtained by adding 35 parts of a mixture of white carbon and polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio 1: 1) and water so that the total amount becomes 100 parts. A9240, B1 to B9240, C1 to C9240, D1 to D9240, E1 to E9240, F1 to F9240, G1 to G9240, H1 to H9240, I1 to I9240, J1 to J9240, K1 to K9240, L1 to L9240, M1 to M9240, Each flowable preparation is obtained by finely pulverizing any one of N1 to N9240, O1 to O9240, P1 to P9240, Q1 to Q9240, R1 to R9240, and S1 to S9240 by a wet pulverization method.

Formulation Example 282
This composition 1-9240 obtained by adding 3 parts of calcium lignin sulfonate, 2 parts of sodium lauryl sulfate, and synthetic silicon hydrous so that the total amount becomes 100 parts, A1 to A9240, B1 to B9240, C1 C9240, D1 to D9240, E1 to E9240, F1 to F9240, G1 to G9240, H1 to H9240, I1 to I9240, J1 to J9240, K1 to K9240, L1 to L9240, M1 to M9240, N1 to N9240, O1 to O9240, Each wettable powder is obtained by thoroughly pulverizing and mixing any one of P1 to P9240, Q1 to Q9240, R1 to R9240, and S1 to S9240.

Formulation Example 283
The present compositions 1-9240, A1 obtained by adding 15 parts of a mixture of white carbon and polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio 1: 1) and water so that the total amount becomes 100 parts A9240, B1 to B9240, C1 to C9240, D1 to D9240, E1 to E9240, F1 to F9240, G1 to G9240, H1 to H9240, I1 to I9240, J1 to J9240, K1 to K9240, L1 to L9240, M1 to M9240, Each flowable preparation is obtained by pulverizing any one of N1 to N9240, O1 to O9240, P1 to P9240, Q1 to Q9240, R1 to R9240, and S1 to S9240 by a wet pulverization method.

  Next, application examples of the composition of the present invention to plant seeds will be shown.

Application example 1
200 kg of any one of the flowable formulations obtained by the method described in Formulation Example 281 or 283 is smeared on 100 kg of dried sorghum seeds using a rotary seed treatment machine (seed dresser, Hans-Ulrich Hege GmbH). Thus, each treated seed is obtained.
In addition, 180 grams of oxabetalinyl is added to 200 ml of any one of the flowable formulations obtained by the method described in Formulation Example 281 or 283, and each treated seed is obtained by a smearing treatment as described above.

Application example 2
200 kg of any one of the flowable formulations obtained by the method described in Formulation Example 281 or 283 is smeared on 100 kg of dried sorghum seeds using a rotary seed treatment machine (seed dresser, Hans-Ulrich Hege GmbH). Thus, each treated seed is obtained.
In addition, 40 grams of flxophenim is added to 200 ml of any one of the flowable formulations obtained by the method described in Formulation Example 281 or 283, and each treated seed is obtained by smearing in the same manner as described above.

Application example 3
Apply 10 ml of any flowable formulation obtained by the method described in Formulation Example 281 or 283 to 10 kg of dry corn seed using a rotary seed processing machine (seed dresser, Hans-Ulrich Hege GmbH). Thus, each treated seed is obtained. As the corn, a genetically modified corn containing a glyphosate resistance gene or a Bt crystal toxin protein gene is used.

Application example 4
40 ml of any one of the flowable formulations obtained by the method described in Formulation Example 281 or 283 is smeared on 10 kg of dried corn seeds using a rotary seed processing machine (seed dresser, Hans-Ulrich Hege GmbH). Thus, each treated seed is obtained.

Application example 5
100 kg of any one of the flowable preparations obtained by the method described in Formulation Example 281 or 283 is smeared on 10 kg of dried corn seeds using a rotary seed processor (seed dresser, Hans-Ulrich Hege GmbH). Thus, each treated seed is obtained.

Application Example 6
Each treated seed is obtained by subjecting 10 kg of dried corn seed to 50 g of any one of the wettable powders obtained by the method described in Formulation Example 282.

Application example 7
Applying 20 ml of any flowable formulation obtained by the method described in Formulation Example 281 or 283 to 10 kg of dried soybean seeds using a rotary seed treatment machine (seed dresser, Hans-Ulrich Hege GmbH) Thus, each treated seed is obtained. As the soybean, a genetically modified soybean containing a glyphosate resistance gene or a Bt crystal toxin protein gene is used.

Application Example 8
100 mg of any one of the flowable formulations obtained by the method described in Formulation Example 281 or 283 is smeared on 10 kg of dried soybean seeds using a rotary seed processor (seed dresser, Hans-Ulrich Hege GmbH). Thus, each treated seed is obtained.

Application example 9
50 kg dry seeds, 50 ml of any one of the flowable formulations obtained by the method described in Formulation Example 281 or 283, are smeared using a rotary seed treatment machine (seed dresser, Hans-Ulrich Hege GmbH). Thus, each treated seed is obtained. As the cotton, a genetically modified cotton containing a glyphosate resistance gene or a Bt crystal toxin protein gene is used.

Application Example 10
50 kg of dried oilseed rape seeds, 50 ml of any one of the flowable formulations obtained by the method described in Formulation Example 281 or 283, is smeared using a rotary seed treatment machine (seed dresser, Hans-Ulrich Hege GmbH). Each treated seed is obtained by treatment. As the oilseed rape, a genetically modified oilseed rape including a glyphosate resistance gene or a Bt crystal toxin protein gene is used.

Application Example 11
Apply 10 ml of any flowable formulation obtained by the method described in Formulation Example 281 or 283 to 10 kg of dried oilseed rape using a rotary seed treatment machine (seed dresser, Hans-Ulrich Hege GmbH). Each treated seed is obtained by treatment.

Application Example 12
50 kg of wheat dry seeds, 50 ml of any one of the flowable preparations obtained by the method described in Formulation Example 281 or 283, are smeared using a rotary seed treatment machine (seed dresser, Hans-Ulrich Hege GmbH). To obtain each treated seed

  Next, the pest control effect of the composition of the present invention is shown by test examples.

Test example 1
The pyridazine compound is dissolved in the mixed solution using 10 μL of a mixed solution of xylene: DMF: surfactant = 4: 4: 1 (volume ratio) per 1 mg of the pyridazine compound. Water containing 0.02% by volume of a spreading agent is added thereto, and a chemical solution containing the pyridazine compound is prepared so that the concentration of the pyridazine compound becomes a predetermined concentration.
Using 10 μL of a mixed solution of xylene: DMF: surfactant = 4: 4: 1 (volume ratio) per 1 mg of the present compound, the present compound is dissolved in the mixed solution. Water containing 0.02% by volume of a spreading agent is added thereto, and a chemical solution containing the present compound is prepared so that the concentration of the present compound becomes a predetermined concentration. When using a commercial preparation containing the present compound, each commercial preparation is mixed with water containing 0.02% by volume of a spreading agent, and a chemical solution containing the present compound so that the concentration of the present compound is a predetermined concentration. To prepare.
The chemical solution containing the present pyridazine compound and the chemical solution containing the present compound are mixed to prepare a test chemical solution.
Cucumber sativus cotyledon leaf pieces (1.5 cm in length) are housed in each well of a 24-well microplate, and 2 cotton aphid adults and 8 larvae are released per well for the test per well. Spray 20 μL of chemical solution. This is the treatment area.
In addition, let the well which sprayed 20 microliters of water containing 0.02 volume% of spreading agents instead of the chemical | medical solution for a test be an untreated section.
After the drug solution for test is dried, the upper part of the microplate is covered with a gas permeable film sheet (trade name: AeroSeal, manufactured by Excel Scientific Inc.), and the number of viable insects in each well is examined 5 days after release.
The control value of the treated and untreated areas is calculated from the following formula.
Control value (%) = {1- (Tai) / (Cai)} × 100
In addition, the character in a formula represents the following meaning.
Cai: Number of surviving insects at the time of the survey in the untreated area Tai: Number of surviving insects at the time of the survey in the treated area

  The results of tests performed according to Test Example 1 are shown below. The composition of the present invention in which the concentration of the present pyridazine compound and the present compound is the concentration described in Table 23 below exhibits excellent control efficacy.

[Table 23]

[Continuation of Table 23]

[Continuation of Table 23]

[Continuation of Table 23]

[Continuation of Table 23]

[Continuation of Table 23]

[Continuation of Table 23]

Test example 2
By seeding any one of the treated corn seeds obtained by the method described in Application Example 3 at a depth of 5 cm at intervals of 15 cm using a seeder, Rhizotonia solani and Pythium spp. ), High control effect can be obtained against Negusare nematode. When seeds treated with a preparation containing an insecticide are used, it is possible to obtain a high control effect against pests having the control effect of the insecticide.

Test example 3
By sowing any one of soybean treated seeds obtained by the method described in Application Example 7, high control against Fusarium oxysporum, Rhizoctonia solani, and soybean cyst nematode An effect can be obtained. When seeds treated with a preparation containing an insecticide are used, it is possible to obtain a high control effect against pests having the control effect of the insecticide.

Test example 4
By sowing any one of the oilseed rape treated seeds obtained by the method described in Application Example 10, it is possible to obtain a high control effect against Rhizotonia solani and Negusare nematode. When seeds treated with a preparation containing an insecticide are used, it is possible to obtain a high control effect against pests having the control effect of the insecticide.

  Pests can be controlled with the pest control composition of the present invention.

Claims (8)

Formula (1):

[Where:
A represents a nitrogen atom or CR ⁶ ;
R ¹ is a C2-C10 alkyl group, a C3-C10 alkenyl group, a C3-C10 alkynyl group, a (C1-C5 alkyl) -O- (C2-C5 alkyl) group, a (C3-C5 alkenyl) -O- (C2 -C5 alkyl) group, (C3-C5 alkynyl) -O- (C2-C5 alkyl) group, (C1-C5 alkyl) -S (O) _m- (C2-C5 alkyl) group, (C3-C5 alkenyl) -S (O) _m- (C2-C5 alkyl) group, (C3-C5 alkynyl) -S (O) _m- (C2-C5 alkyl) group, or (C1-C5 alkyl) -C (O)-( C1-C5 alkyl) group (wherein R ¹ has one or more halogen atoms),
R ² and R ³ each independently represent a hydrogen atom, a C1-C6 alkyl group optionally having one or more halogen atoms, a C2-C6 alkoxycarbonyl group, a cyano group, or a halogen atom,
R ⁴ represents a C1-C6 chain hydrocarbon group which may have one or more halogen atoms,
R ⁵ is a C1-C6 chain hydrocarbon group which may have one or more halogen atoms, a phenyl group which may have one or more atoms or groups selected from Group A, and a group B. Any of the five-membered aromatic heterocyclic groups selected from the group C (the five-membered aromatic heterocyclic group may have one or more atoms or groups selected from the group A). 6-membered aromatic heterocyclic group (the 6-membered aromatic heterocyclic group may have one or more atoms or groups selected from group A), and any 3- 7-membered non-aromatic heterocyclic group (The 3-7-membered non-aromatic heterocyclic group may have one or more atoms or groups selected from the group consisting of halogen atoms and C1-C6 alkyl groups. ^{), OR 7, NR 8 R} 9, NR 8 C (O) R 10, NR 8 C (O) OR 11, NR 8 C (O) NR 12 R 13 ^{N = CHNR 12 R 13, N} = S (O) x R 12 R 13, S (O) y R 12, C (O) OR 8, cyano group, or a halogen atom,
R ⁶ represents a hydrogen atom or a halogen atom,
R ⁷ represents a hydrogen atom, a C1-C6 alkyl group, a C3-C6 alkenyl group, a C3-C6 alkynyl group, a (C1-C3 alkyl) -O- (C1-C3 alkyl) group, or a (C1-C3 alkyl) -S. (O) _y- (C1-C3 alkyl) group, C3-C7 cycloalkyl group, (C3-C7 cycloalkyl)-(C1-C3 alkyl) group (provided that the C1-C6 alkyl group, C3-C6 alkenyl group) , C3-C6 alkynyl group, (C1-C3 alkyl) -O- (C1-C3 alkyl) group, (C1-C3 alkyl) -S (O) _y- (C1-C3 alkyl) group, C3-C7 cycloalkyl Group, and (C3-C7 cycloalkyl)-(C1-C3 alkyl) group may have one or more halogen atoms), or phenyl C1-C3 alkyl group (the phenyl C1-C Phenyl moiety of the alkyl group may have one or more atoms or groups selected from the group A.) Represent,
R ⁸ represents a hydrogen atom, a C1-C6 alkyl group optionally having one or more halogen atoms, a C3-C6 alkenyl group optionally having one or more halogen atoms, or one or more halogen atoms. Represents a C3-C6 alkynyl group which may have,
R ⁹ represents a hydrogen atom, a C1-C6 alkyl group, a C3-C6 alkenyl group, a C3-C6 alkynyl group, a (C1-C3 alkyl) -O- (C1-C3 alkyl) group, or a (C1-C3 alkyl) -S. (O) _y- (C1-C3 alkyl) group, C3-C7 cycloalkyl group, (C3-C7 cycloalkyl)-(C1-C3 alkyl) group (provided that the C1-C6 alkyl group, C3-C6 alkenyl group) , C3-C6 alkynyl group, (C1-C3 alkyl) -O- (C1-C3 alkyl) group, (C1-C3 alkyl) -S (O) _y- (C1-C3 alkyl) group, C3-C7 cycloalkyl Group, and (C3-C7 cycloalkyl)-(C1-C3 alkyl) group may have one or more halogen atoms), cyano C1-C6 alkyl group, phenyl C1-C3 alkyl group. A group (the phenyl portion of the phenyl C1-C3 alkyl group may have one or more atoms or groups selected from group A), or a (5- or 6-membered heteroaryl) C1-C3 alkyl group (the (5- or 6-membered heteroaryl) the 5- or 6-membered heteroaryl part of the C1-C3 alkyl group may have one or more atoms or groups selected from group A),
R ¹⁰ represents a hydrogen atom, a C1-C6 alkyl group, a C3-C6 alkenyl group, a C3-C6 alkynyl group, a C3-C7 cycloalkyl group, a (C3-C7 cycloalkyl)-(C1-C3 alkyl) group (provided that The C1-C6 alkyl group, C3-C6 alkenyl group, C3-C6 alkynyl group, C3-C7 cycloalkyl group, and (C3-C7 cycloalkyl)-(C1-C3 alkyl) group have one or more halogen atoms. Or a phenyl C1-C3 alkyl group (the phenyl portion of the phenyl C1-C3 alkyl group may have one or more atoms or groups selected from group A);
R ¹¹ has a C1-C6 alkyl group optionally having one or more halogen atoms, a C3-C6 alkenyl group optionally having one or more halogen atoms, and one or more halogen atoms. Or a C3-C6 alkynyl group, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, a (C3-C7 cycloalkyl)-(C1-C3 alkyl) group (provided that the (C3-C7 The cycloalkyl)-(C1-C3 alkyl) group may have one or more halogen atoms), or a phenyl C1-C3 alkyl group (the phenyl portion of the phenyl C1-C3 alkyl group is selected from group A) It may have one or more atoms or groups.
)
R ¹² and R ¹³ each independently represent a C1-C6 alkyl group optionally having one or more halogen atoms,
R ¹⁴ is a hydrogen atom, a C1-C6 alkyl group optionally having one or more halogen atoms, a C2-C6 alkylcarbonyl group optionally having one or more halogen atoms, or one or more halogen atoms. Represents a C2-C6 alkoxycarbonyl group optionally having
n represents 0, 1, or 2;
m represents 0, 1, or 2;
p represents 0, 1, 2 or 3 (wherein, when p represents 2 or 3, a plurality of R ⁵ may be the same or different from each other);
x represents 0 or 1,
y represents 0, 1, or 2.
Group A: a C1-C6 alkyl group that may have one or more halogen atoms, a C1-C6 alkoxy group that may have one or more halogen atoms, or one or more halogen atoms A good C1-C6 alkylsulfanyl group, a C1-C6 alkylsulfinyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally having one or more halogen atoms, a cyano group, and A group consisting of halogen atoms.
Group B:

Group C:

Group D:

Or a N oxide compound thereof,
A pest control composition comprising one or more compounds selected from the following group (a) or the following group (b).
Group (a):
The group consisting of the following subgroups a-1, a-2, a-3, a-4, a-5, a-6 and a-7.
Subgroup a-1:
Acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, flupiradifurone, sulfoxafurol, triflumezopyrim, dichloromesothiaz and compounds represented by the following formula

A group of competitive modulators of nicotinic acetylcholine receptors.
Subgroup a-2:
Acrinatrin, Aleslin, Bifenthrin, Kappabifenthrin, Bioarethrin, Bioresmethrin, Cycloproton, Cyfluthrin, Beta-cyfluthrin, Cyhalothrin, Gamma cyhalothrin, Lambda cyhalothrin, Cypermethrin, Alpha cypermethrin, Betacypermethrin, Theta Permethrin, zeta-cypermethrin, sigma-permethrin, ciphenothrin, deltamethrin, empentrin, esfenvalerate, etofenprox, fenpropatoline, fenvalerate, flucitrinate, flumethrin, fluvinate, taufulvalinate, halfenprox, hepta Flutrin, imiprothrin, cadreslin, meperfluthrin, monfluorotrin, permethrin, phenothrin Sodium channel modulator consisting of praretrin, pyrethrin, resmethrin, silafluophene, tefluthrin, kappafluthrin, tetramethrin, tetramethylfluthrin, tralomethrin, transfluthrin, benfluthrin, flufenprox, flumethrin, flamethrin, methfluthrin, profluthrin and dimefluthrin. .
Subgroup a-3:
A group of GABAergic chloride channel blockers consisting of ethiprol, fipronil and flupiprol, and a group of GABAergic chloride channel allosteric modulators consisting of afoxolanel, fluralanel, brofuranilide and floxamethamide.
Subgroup a-4:
A group of ryanodine receptor modulators consisting of chlorantraniliprole, cyantranylprolol, cyclaniliprol, fulvendiamide, tetraniliprol and cyhalodiamide.
Subgroup a-5:
Alanicarb, aldicarb, bendiocarb, benfuracarb, butocarboxym, butoxycarboxym, carbaryl, carbofuran, carbosulfan, ethiophene carb, fenobucarb, formethanate, furthiocarb, isoprocarb, methiocarb, mesomil, metolcarb, oxamyl, pyrimicarb, dioxycarb, propoxyl A group of carbamate acetylcholinesterase inhibitors consisting of thiophanox, triazamate, trimetacarb, XMC and xylylcarb.
Subgroup a-6:
A group of nematicidal active compounds consisting of abamectin, fluenesulfone, thioxazaphene, and fluazaindolizine.
Subgroup a-7:
Mycorrhizal fungi, Arthrobotris dacteroides, Bacillus thuringiensis, Bacillus films, Bacillus megaterium, Bacillus amyloliquefaciens, Hilstera rosiliensis, Hilstera minnesotensis, Monacrosporium fimatopagum, Pasteurian nisawae A group of microbial materials consisting of, Pasteuria penetrans, Pasteuria usgae, Verticillium chlamydosporium and Harpin protein.
Group (b):
A group consisting of the following subgroups b-1, b-2, b-3, b-4, b-5, b-6, b-7, b-8 and b-9.
Subgroup b-1:
Azaconazole, viteltanol, bromconazole, cyproconazole, difenoconazole, dinicoazole, diniconazole M, epoxiconazole, etaconazole, phenalimol, fenbuconazole, fluquinconazole, quinconazole, flusilazole, flutriazole, hexaconazole, imazalil, Imibenconazole, ipconazole, metconazole, microbutanyl, nuarimol, oxpoconazole, oxpoconazole fumarate, pefazoate, penconazole, prochloraz, propiconazole, prothioconazole, pyrifenox, pyrisoxazole, cimeconazole, tebuconazole, tetrabuconazole Conazole, triadimephone, triadimenol, triflumizole, trifolin and tritico A group of sterol biosynthesis inhibitors consisting of nazole.
Subgroup b-2:
Azoxystrobin, cumoxystrobin, dimoxystrobin, enoxastrobin, famoxadone, fenamidone, phenaminestrobin, fluphenoxystrobin, floxastrobin, cresoxime-methyl, mandestrobin, methinostrobin, A group of Qo inhibitors consisting of orissastrobin, picoxystrobin, pyraclostrobin, pyramethostrobin, pyroxystrobin, trifloxystrobin, pyribencarb, triclopyricarb, cyazofamid and amisulbrom.
Subgroup b-3:
A group of RNA polymerase I inhibitors consisting of benalaxyl, benalaxyl M, furaxyl, metalaxyl, metalaxyl M, oxadixyl and oflase.
Subgroup b-4:
Benodanyl, benzobindiflupyr, bixaphene, boscalid, carboxin, fenfram, fluopyram, flutolanil, fluxapyroxad, furametopyr, isophetamide, isopyrazam, mepronil, oxycarboxyl, pentiopyrad, penflufen, cedaxane, tifluzamide, pyradiflumide Phen, 3-difluoromethyl-1-methyl-N- (1,1,3-trimethylindan-4-yl) pyrazole-4-carboxamide, 3-difluoromethyl-1-methyl-N-[(3R) -1 , 1,3-Trimethylindan-4-yl] pyrazole-4-carboxamide, 3-difluoromethyl-N- (7-fluoro-1,1,3-trimethylindan-4-yl) -1-methylpyrazole-4 -Carboxa 3-difluoromethyl-N-[(3R) -7-fluoro-1,1,3-trimethylindan-4-yl] -1-methylpyrazole-4-carboxamide and N-cyclopropyl-3- (difluoro A group of succinate dehydrogenase inhibitors consisting of (methyl) -5-fluoro-N- (5-chloro-2-isopropylbenzyl) -1-methyl-1H-pyrazole-4-carboxamide.
Subgroup b-5:
A group of β-tubulin polymerization inhibitors consisting of benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate, thiophanate methyl, dietofencarb, zoxamide and ethaboxam.
Subgroup b-6:
Multi-acting contact active compound consisting of felbam, manzeb, manneb, methyleum, propineb, thiuram, dineb, ziram, captan, captahol, holpet, chlorothalonil, tolylfluanid, guazatine, iminotadine, anilazine, dithianone, quinomethionate and fluorimide Group of.
Subgroup b-7:
A group of cellulose synthesis inhibitors consisting of dimethomorph, flumorph, pyrimorph, benchavaricarb, benchavaricarb isopropyl, iprovaricarb, varifenalate and mandipropamide.
Subgroup b-8:
A group of MAP / histidine kinase inhibitors in osmotic signaling consisting of fenpicuronyl, fludioxonil, clozolinate, iprodione, procymidone and vinclozolin.
Subgroup b-9:
A group of other fungicides consisting of tolcrofos methyl, oxathiapiproline, pical butrazox, fluopicolide and silthiofam.   The pest according to claim 1, wherein the content ratio of the compound represented by the formula (1) to one or more compounds selected from the group (a) is 100: 1 to 1: 100 by weight. Control composition.   The pest according to claim 1, wherein the content ratio of the compound represented by the formula (1) to one or more compounds selected from the group (a) is 10: 1 to 1:10 by weight. Control composition.   The pest according to claim 1, wherein the ratio of the content of the compound represented by the formula (1) and one or more compounds selected from the group (b) is 10,000: 1 to 1: 100 by weight. Control composition.   The pest according to claim 1, wherein the content ratio of the compound represented by the formula (1) and one or more compounds selected from the group (b) is 1000: 1 to 1:10 by weight. Control composition.   A pest control method comprising a step of applying an effective amount of the pest control composition according to any one of claims 1 to 5 to a pest or a habitat of the pest.   A pest control method comprising a step of applying an effective amount of the pest control composition according to any one of claims 1 to 5 to a plant, a plant seed, a bulb or a soil for cultivating a plant.   A plant seed or bulb to which an effective amount of the pesticidal composition according to any one of claims 1 to 5 is attached.