JP2004155693A - Insecticidal, acaricidal, nematicidal, fungicidal or bactericidal composition, and method for controlling disease and insect pest - Google Patents

Insecticidal, acaricidal, nematicidal, fungicidal or bactericidal composition, and method for controlling disease and insect pest Download PDF

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JP2004155693A
JP2004155693A JP2002322041A JP2002322041A JP2004155693A JP 2004155693 A JP2004155693 A JP 2004155693A JP 2002322041 A JP2002322041 A JP 2002322041A JP 2002322041 A JP2002322041 A JP 2002322041A JP 2004155693 A JP2004155693 A JP 2004155693A
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Prior art keywords
alkyl
substituted
optionally substituted
haloalkyl
compound
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Japanese (ja)
Inventor
Toshiro Miyake
敏郎 三宅
Kohei Inoue
公平 井上
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Nissan Chemical Corp
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Nissan Chemical Corp
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    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02ATECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Abstract

<P>PROBLEM TO BE SOLVED: To obtain a new insecticidal, acaricidal, nematicidal, fungicidal or bactericidal composition and to provide a method for controlling diseases and insect pests. <P>SOLUTION: The insecticidal, acaricidal, nematicidal, fungicidal or bactericidal composition comprises one or more kinds of acrylonitrile compounds represented by formula (1) [A is a specific heterocyclic group which may be substituted with a specified group; B is H, a 2-4C haloalkyl, tetrahydropyranyl, or the like; G is H, a halogen, a 2-6C alkyl, or the like] and one or more kinds selected from a specific insecticidal, acaricidal, nematicidal, fungicidal and bactericidal compounds. The method for controlling diseases and insect pests comprises treatment with one or more kinds of the acrylonitrile compounds represented by formula (1) and one or more kinds selected from the specific insecticidal, acaricidal, nematicidal, fungicidal and bactericidal compounds simultaneously or adjacently. <P>COPYRIGHT: (C)2004,JPO

Description

【0001】
【発明の属する技術分野】
本発明は、アクリロニトリル化合物と、公知の殺虫剤、殺ダニ剤、殺線虫剤、殺菌剤又は殺バクテリア剤の有効成分化合物とを混合してなることを特徴とする病害虫防除剤に関するものである。
【0002】
【従来の技術】
アクリロニトリル誘導体が、農薬又は水中生物付着防止剤として使用されることが知られている(例えば、特許文献1参照。)。
【0003】
また、アクリロニトリル誘導体と公知の殺虫剤、殺ダニ剤、殺菌剤とを含有する組成物が知られている(例えば、特許文献2参照。)。
【0004】
【特許文献1】
国際公開第97/040009号パンフレット
【0005】
【特許文献2】
特開平11−124306号公報
【0006】
【発明が解決しようとする課題】
今日、農園芸病害虫、森林病害虫、あるいは衛生病害虫等各種病害虫の防除を目的とする殺虫・殺ダニ・殺菌剤の開発が広く進められ、多種多様な薬剤が実用に供されている。しかしながら、近年、こうした薬剤の長年にわたる使用により害虫が殺虫剤抵抗性を、また病原菌が殺菌剤耐性を獲得した結果、従来の薬剤による防除が困難となる場面が増えてきている。またこうした薬剤の一部は毒性が高く、あるものは環境中に長期に残留することにより生態系を撹乱しつつある。よって、高度な病害虫防除効果を有するだけではなく、低毒性であり且つ低残留性の新規な薬剤の開発が常に期待されている。
【0007】
しかしその一方、生物群としての昆虫や病原菌の多様性、その加害様式、加害場面の多様性を考えれば、これら新規の薬剤、あるいは既存の公知薬剤を単独で使用するだけでは、全ての防除場面で全ての病害虫を有効に防除することははなはだ難しい。そこで、複数の殺虫、殺ダニ、殺線虫、殺菌または殺バクテリア剤を適切に組み合わせてより高い防除効力を誘導し、防除困難な有害生物を防除する新たな方法もまた、強く要望されるに至っている。
【0008】
【課題を解決するための手段】
本発明者らは、このような状況に鑑み、優れた防除活性を示し、かつ哺乳動物、魚類および天敵等の有用生物に対して悪影響の少ない病害虫防除剤を開発する為に鋭意研究を続けた結果、以下の式(1)で表されるアクリロニトリル化合物と、公知の殺虫、殺ダニ、殺線虫、殺菌又は殺バクテリア化合物を含有する殺虫、殺ダニ、殺線虫、殺菌又は殺バクテリア組成物が、単独の使用からは予測し得ない優れた相乗的殺虫、殺ダニ、殺線虫、殺菌又は殺バクテリア効果を奏することを見いだし、本発明を完成した。
【0009】
即ち、本発明は下記〔1〕又は〔2〕の組成物(以下、本発明組成物と称する。)、及び〔3〕〜〔6〕の防除方法(以下、本発明方法と称する。)に関するものである。
【0010】
〔1〕 以下の式(1)で表されるアクリロニトリル化合物の1種以上と、以下の化合物群Aより選ばれる化合物の1種以上を含有する殺虫、殺ダニ、殺線虫、殺菌又は殺バクテリア組成物。
【0011】
式(1):
【0012】
【化7】

Figure 2004155693
【0013】
[式中、 Aは、
【0014】
【化8】
Figure 2004155693
【0015】
【化9】
Figure 2004155693
【0016】
【化10】
Figure 2004155693
【0017】
【化11】
Figure 2004155693
【0018】
【化12】
Figure 2004155693
【0019】
であり、
Bは、H、CR、CHR、C〜Cハロアルキル、テトラヒドロピラニル、Si(CH、SORe、SONHRb、SONRaRb、C(S)NHRb、C(S)NRaRb、C(O)Rf、P(O)RgRh、P(S)RgRh、アルカリ金属、アルカリ土類金属またはNHRiRjRkであり、Gは、H、ハロゲン、C〜Cアルキル、Rcで置換されたC〜Cアルキル、C〜Cハロアルキル、C〜Cアルキルで置換されていてもよいC〜Cシクロアルキル、C〜Cアルコキシ、C〜Cアルケニルオキシ、C〜Cアルキニルオキシ、C〜Cハロアルコキシ、C〜Cアルキルスルフェニル、C〜Cアルキルスルフィニル、C〜Cアルキルスルホニル、C〜Cアルケニルスルフェニル、C〜Cアルケニルスルフィニル、C〜Cアルケニルスルホニル、C〜Cアルキニルスルフェニル、C〜Cアルキニルスルフィニル、C〜Cアルキニルスルホニル、C〜Cハロアルキルスルフェニル、C〜Cハロアルキルスルフィニル、C〜Cハロアルキルスルホニル、C〜Cハロアルケニルスルフェニル、C〜Cハロアルケニルスルフィニル、C〜Cハロアルケニルスルホニル、NO、CN、−NU、ナフチル、Rcで置換されたメトキシ、C〜Cアルコキシカルボニル、C〜Cアルコキシアルキル、C〜Cアルキルカルボニル、C〜Cハロアルキルカルボニル、C〜Cアルキルカルボニルオキシ、C〜Cハロアルキルカルボニルオキシ、C〜Cジアルキルアミノカルボニルオキシ、Zで置換されていてもよいフェニル、Zで置換されていてもよいフェノキシ、Zで置換されていてもよいベンゾイル、Zで置換されていてもよいピリジル、Zで置換されていてもよいピリジルオキシ、Zで置換されていてもよいチエニル、隣接した置換位置で結合したメチレンジオキシ、隣接した置換位置で結合したハロメチレンジオキシ及び−N=CTの中から選ばれる1ないし4個の置換基、または隣接した置換位置で結合したアルキレン基によって形成される5ないし8員環であり、
Y、Y及びYは、各々独立にH、ハロゲン、C〜Cアルキル、C〜Cハロアルキル、C〜Cアルコキシ、C〜Cハロアルコキシ、C〜Cアルキルスルフェニル、C〜Cアルキルスルフィニル、C〜Cアルキルスルホニル、C〜Cハロアルキルスルフェニル、C〜Cハロアルキルスルフィニル、C〜Cハロアルキルスルホニル、NOまたはCNであるか、または隣接した置換位置で結合したアルキレン基によって形成される5員環、6員環、7員環もしくは8員環であり、
は、C〜CアルキルまたはC〜Cハロアルキルであり、
Zは、各々独立して、ハロゲン、C〜Cアルキル、C〜Cハロアルキル、C〜Cアルコキシ、C〜Cハロアルコキシ、C〜Cアルキルスルフェニル、C〜Cアルキルスルフィニル、C〜Cアルキルスルホニル、C〜Cアルケニルスルフェニル、C〜Cアルケニルスルフィニル、C〜Cアルケニルスルホニル、C〜Cハロアルキルスルフェニル、C〜Cハロアルキルスルフィニル、C〜Cハロアルキルスルホニル、NO、CN、−NU及びC〜Cアルコキシカルボニルの中から選ばれる1ないし5個の置換基であり、
、R、R及びRaは、各々独立にC〜Cアルキルであり、
Rbは、H、C〜Cアルキル、またはTで置換されていてもよいフェニルであり、
Rcは、ハロゲン、C〜Cアルキル、C〜Cアルコキシ及びC〜Cハロアルキルの中から任意に選ばれる1種以上で置換されていてもよいフェニルであり、
Rdは、ハロゲン、C〜Cアルキル及びC〜Cハロアルキルの中から任意に選ばれる1種以上で置換されていてもよいベンゾイルであり、
Reは、C〜Cアルキル、C〜Cハロアルキル、またはTで置換されてい
てもよいフェニルであり、
Rfは、C〜C20アルキル、C〜Cアルケニル、C〜Cハロアルキル、C〜Cアルコキシアルキル、C〜Cハロシクロアルキル、Rcで置換されたC〜Cアルキル、C〜Cアルキルで置換されていてもよいC〜Cシクロアルキル、Rcで置換されたシクロアルキル、Rc及びC〜Cアルキルで置換されたシクロプロピル、Rc及びハロゲンで置換されたC〜Cシクロアルキル基、T及びC〜Cアルキルで置換されたシクロプロピル基、Rcで置換されたC〜Cアルケニル、C〜Cアルコキシ、C〜Cハロアルコキシ、C〜Cアルケニルオキシ、C〜Cアルキルで置換されていてもよいC〜Cシクロアルコキシ、ベンジルオキシ、COORa、−NU、Tで置換されていてもよいフェニル、Tで置換されていてもよいフェノキシ、ナフチル、Tで置換されていてもよいピリジルまたはA−1〜A−140であり、
Rg及びRhは各々独立に、OH、フェニル、C〜Cアルキル、C〜CアルコキシまたはC〜Cアルキルスルフェニルであり、
Ri、Rj及びRkは各々独立に、H、C〜Cアルキル、C〜Cアルケニル、C〜Cアルキル基で置換されていてもよいC〜Cシクロアルキル基またはベンジルであるか、あるいはRi、Rj及びRkのうちの2個が、それぞれが結合している窒素原子と共に酸素原子、窒素原子または硫黄原子を含有していてもよい5ないし8員環基を形成してもよく、
は、ハロゲン、C〜Cアルキル、C〜CハロアルキルまたはC〜Cアルコキシであり、
は、ハロゲンで置換されていてもよいC〜Cアルケニルであり、
は、ハロゲン、C〜Cアルキル、C〜Cハロアルキル、C〜Cアルコキシ、C〜Cハロアルコキシ、C〜Cアルキルスルフェニル、C〜Cアルキルスルフィニル、C〜Cアルキルスルホニル、C〜Cハロアルキルスルフェニル、C〜Cハロアルキルスルフィニル、C〜Cハロアルキルスルホニル、NO、CN、CHO、−NU、フェニル及びフェノキシの中から任意に選ばれる1ないし5個の置換基であり、
及びUは、各々独立に、H、C〜Cアルキル、COORa、フェニルまたはベンジルを表すか、あるいはUとUとが結合している窒素原子と共に酸素原子、窒素原子または硫黄原子を含有していてもよい5ないし8員環基を形成してもよく、
mは、置換基の数を表し、0、1、2または3であり、
nは、置換基の数を表し、0、1、2、3または4であり、
pは、置換基の数を表し、0、1または2であり、
qは、置換基の数を表し、0または1である。(但し、m、n及びpが2以上の整数を表す場合は、その置換基は同一か相互に異なってもよい。)]。
【0020】
化合物群A:アシベンゾラルーS−メチル(acibenzolar−S−methyl)、アシルアミノベンザミド(acylaminobenzamide)、アンバム(amobam)、アムプロピルホス(ampropyfos)、アニラジン(anilazine)、アザコナゾール(azaconazole)、アゾキシストロビン(azoxystrobin)、ベナラキシル(benalaxyl)、ベノダニル(benodanil)、ベノミル(benomyl)、ベンチアゾール(benthiazole)、ベンザマクリル(benzamacril)、ビナパクリル(binapacryl)、ビフェニル(biphenyl)、ビテルタノール(bitertanol)、ベトキサジン(bethoxazine)、ボルドー液(bordeaux mixture)、ブラストサイジン−S(blasticidin−S)、ブロモコナゾール(bromoconazole)、ブピリメート(bupirimate)、ブチオベート(buthiobate)、カルシウムポリスルフィド(calcium polysulfide)、キャプタフォール(captafol)、キャプタン(captan)、カッパーオキシクロリド(copper oxychloride)、カルプロパミド(carpropamid)、カルベンダジン(carbendazim)、カルボキシン(carboxin)、CGA−279202、キノメチオネート(chinomethionat)、クロベンチアゾン(chlobenthiazone)、クロルフェナゾール(chlorfenazol)、クロロネブ(chloroneb)、クロロタロニル(chlorothalonil)、クロゾリネート(chlozolinate)、クフラネブ(cufraneb)、シモキサニル(cymoxanil)、シプロコナゾール(cyproconazol)、シプロジニル(cyprodinil)、シプロフラム(cyprofuram)、ダゾメット(dazomet)、デバカルブ(debacarb)、ジクロロフェン(dichlorophen)、ジクロブトラゾール(diclobutrazol)、ジクロフラニド(diclhlofluanid)、ジクロメジン(diclomedine)、ジクロラン(dicloran)、ジエトフェンカルブ(diethofencarb)、ジクロシメット(diclocymet)、ジフェノコナゾール(difenoconazole)、ジフルメトリン(diflumetorim)、ジメチリモール(dimethirimol)、ジメトモルフ(dimethomorph)、ジニコナゾール(diniconazole)、ジニコナゾール−M(diniconazole−M)、ジノカップ(dinocap)、ジフェニルアミン(diphenylamine)、ジピリチオン(dipyrithione)、ジタリムホス(ditalimfos)、ジチアノン(dithianon)、ドデモルフ(dodemorph)、ドジン(dodine)、ドラゾクソロン(drazoxolon)、エデフェノホス(edifenphos)、エポキシコナゾール(epoxiconazole)、エタコナゾール(etaconazole)、エチリモル(ethirimol)、エトリジアノール(etridiazole)、ファモキサゾン(famoxadone)、フェナリモル(fenarimol)、フェブコナゾール(febuconazole)、フェナミドン(fenamidone)、フェンダゾスラム(fendazosulam)、フェンフラム(fenfuram)、フェンヘキサミド(fenhexamid)、フェンピクロニル(fenpiclonil)、フェンプロピジン(fenpropidin)、フェンプロピモルフ(fenpropimorph)、フェンチン(fentin)、フェルバン(ferbam)、フェリムゾン(ferimzone)、フルアジナム(fluazinam)、フルジオキソニル(fludioxonil)、フルオロイミド(fluoroimide)、フルキンコナゾール(fluquinconazole)、フルシラゾール(flusilazole)、フルスルファミド(flusulfamide)、フルトラニル(flutolanil)、フルトリアフォール(flutriafol)、フォルペット(folpet)、フォセチル−アルミニウム(fosetyl−aluminium)、フベリダゾール(fuberidazole)、フララキシル(furalaxyl)、フラメトピル(furametpyr)、グアザチン(guazatine)、ヘキサクロロベンゼン(hexachlorobenzene)、ヘキサコナゾール(hexaconazole)、ヒメキサゾール(hymexazol)、イマザリル(imazalil)、イミベンコナゾール(imibenconazole)、イミノクタジン(iminoctadine)、イプコナゾール(ipconazole)、イプロベンホス(iprobenfos)、イプロジオン(iprodione)、イソプロチオラン(isoprothiolane)、イプロバリカルブ(iprovalicarb)、カスガマイシン(kasugamycin)、クレソキシム−メチル(kresoxim−methyl)、マンカッパー(mancopper)、マンコゼブ(mancozeb)、マンネブ(maneb)、メパニピリム(mepanipyrim)、メプロニル(mepronil)、メタラキシル(metalaxyl)、メトコナゾール(metconazole)、メタスルホカルブ(methasulfocarb)、メチラム(metiram)、メトミノストロビン(metominostrobin)、ミクロブタニル(myclobutanil)、MTF−753、ナバム(nabam)、ニッケルビス(ジメチルジチオカーバメート)(nickel bis(dimethyldithiocarbamate))、ニトロタール−イソプロピル(nitrothal−isopropyl)、ヌアリモル(nuarimol)、NNF−9425、オクチリノン(octhilinone)、オフレース(ofurace)、オキサジキシル(oxadixyl)、オキシカルボキシン(oxycarboxin)、オキポコナゾールフマール酸塩(oxpoconazole fumarate)、ペフラゾエート(pefurzoate)、ペンコナゾール(penconazole)、ペンシクロン(pencycuron)、フタライド(phthalide)、ピペラリン(piperalin)、ポリオキシン(polyoxins)、炭酸水素カリウム(potassium hydrogen carbonate)、プロベナゾール(probenazole)、プロクロラズ(prochloraz)、プロシミドン(procymidone)、プロパモカルブ塩酸塩(propamocarb hydrochloride)、プロピコナゾール(propiconazole)、プロピネブ(propineb)、ピラゾホス(pyrazophos)、ピリフェノックス(pyrifenox)、ピリメタニル(pyrimethanil)、ピロキュロン(pyroquilon)、キノメチオネート(quinomethionate)、キノキシフェン(quinoxyfen)、キントゼン(quintozene)、RH7281、炭酸水素ナトリウム(sodium hydrogen carbonate)、次亜塩素酸ナトリウム(sodium hypochlorite)、硫黄(sulfur)、スピロキサミン(spiroxamine)、テブコナゾール(tebuconazole)、テクナゼン(tecnazene)、テトラコナゾール(tetraconazole)、チアベンダゾール(thiabendazole)、チアジアジン(thiadiazin/milneb)、チフルザミド(thifluzamide)、チオファネート−メチル(thiophanate−methyl)、チラム(thiram)、トルクロホス−メチル(tolclofos−methyl)、トリルフラニド(tolylfluanid)、トリアジメホン(triadimefon)、トリアジメノール(toriadimenol)、トリアゾキシド(triazoxide)、トリシクラゾール(tricyclazole)、トリデモルフ(tridemorph)、トリフルミゾール(triflumizole)、トリホリン(triforine)、トリチコナゾール(triticonazole)、バリダマイシン(validamycin)、ビンクロゾリン(vinclozolin)、硫酸亜鉛(zinc sulfate)、ジネブ(zineb)、ジラム(ziram)、シイタケ菌糸体抽出物、ストレプトマイシン(streptomycin)、テクロフタラム(tecloftalam)、オキシテトラサイクリン(oxyterracycline)、オキソリニックアシド(oxolinic acid)、アルドキシカルブ(aldoxycarb)、カズサホス(cadusafos)、フォスチアゼート(fosthiazate)、フォスチエタン(fosthietan)、オキサミル(oxamyl)、フェナミホス(fenamiphos)、アセキノシル(acequinocyl)、ブロモプロピレート(bromopropylate)、チノメチオネート(chinomethionat)、クロロベンジラート(chlorobezilate)、サイヘキサチン(cyhexatine)、ジコフォール(dicofol)、ジエノクロール(dienochlor)、エトキサゾール(etoxazole)、フェナザキン(fenazaquin)、フェンブタチンオキシド(fenbutatin oxide)、フェンプロパトリン(fenpropathrin)、フェンプロキシメート(fenproximate)、ハルフェンプロックス(halfenprox)、ヘキシチアゾックス(hexythiazox)、ミルベメクチン(milbemectin)、プロパルギット(propargite)、ピリダベン(pyridaben)、ピリミジフェン(pyrimidifen)、テブフェンピラド(tebufenpyrad)、アバメクチン(abamectin)、アセフェート(acephate)、アセタミピリド(acetamipirid)、アルディカルブ(aldicarb)、アレスリン(allethrin)、アジンホス−メチル(azinphos−methyl)、ベンジオカルブ(bendiocarb)、ベンフラカルブ(benfuracarb)、ベンスルタップ(bensultap)、ブプロフェジン(buprofezin)、ブトカルボキシン(butocarboxim)、カルバリル(carbaryl)、カルボフラン(carbofuran)、カルボスルファン(carbosulfan)、カルタップ(cartap)、クロルフェナピル(chlorfenapyr)、クロルピリホス(chlorpyrifos)、クロルフェンビンホス(chlorfenvinphos)、クロルフルアズロン(chlorfluazuron)、クロチアニジン(clothianidin)、クロマフェノジド(chromafenozide)、クロピリホス−メチル(chlorpyrifos−methyl)、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)、シペルメトリン(cypermethrin)、シロマジン(cyromazine)、シハロトリン(cyhalothrin)、ラムダ−シハロトリン(lambda−cyhalothrin)、デルタメトリン(deltamethrin)、ジアフェンチウロン(diafenthiuron)、ダイアジノン(diazinon)、ジアクロデン(diacloden)、ジフルベンズロン(diflubenzuron)、ジメチルビンホス(dimethylvinphos)、ジオフェノラン(diofenolan)、ジスルフォトン(disulfoton)、ジメトエート(dimethoate)、エマメクチンベンゾエート(emamectin−benzoate)、EPN、エスフェンバレレート(esfenvalerate)、エチオフェンカルブ(ethiofencarb)、エチプロール(ethiprole)、エトフェンプロックス(etofenprox)、エトリムホス(etrimfos)、フェニトロチオン(fenitrothion)、フェノブカルブ(fenobucarb)、フェノキシカーブ(fenoxycarb)、フェンプロパトリン(fenpropathrin)、フェンバレレート(fenvalerate)、フィプロニル(fipronil)、フルアクリピリム(fluacrypyrim)、フルシトリネート(flucythrinate)、フルフェノクスウロン(flufenoxuron)、フルフェンプロックス(flufenprox)、タウ−フルバリネート(tau−fluvalinate)、ホノホス(fonophos)、フォルメタネート(formetanate)、フォルモチオン(formothion)、フラチオカルブ(furathiocarb)、ハロフェノジド(halofenozide)、ヘキサフルムロン(hexaflumuron)、ヒドラメチルノン(hydramethylnon)、イミダクロプリド(imidacloprid)、イソフェンホス(isofenphos)、インドキサカルブ(indoxacarb)、イソプロカルブ(isoprocarb)、イソキサチオン(isoxathion)、ルフェヌウロン(lufenuron)、マラチオン(malathion)、メタルデヒド(metaldehyde)、メタミドホス(methamidophos)、メチダチオン(methidathion)、メタクリホス(methacrifos)、メタルカルブ(metalcarb)、メソミル(methomyl)、メソプレン(methoprene)、メトキシクロール(methoxychlor)、メトキシフェノジド(methoxyfenozide)、モノクロトホス(monocrotophos)、ムスカルーレ(muscalure)、ニジノテフラン(nidinotefuran)、ニテンピラム(nitenpyram)、オメトエート(omethoate)、オキシデメトン−メチル(oxydemeton−methyl)、オキサミル(oxamyl)、パラチオン(parathion)、パラチオン−メチル(parathion−methyl)、ペルメトリン(permethrin)、フェントエート(phenthoate)、フォキシム(phoxim)、ホレート(phorate)、ホサロン(phosalone)、ホスメット(phosmet)、ホスファミドン(phosphamidon)、ピリミカルブ(pirimicarb)、ピリミホス−メチル(pirimiphos−methyl)、プロフェノホス(profenofos)、プロトリフェンブト(protrifenbute)、ピメトロジン(pymetrozine)、ピラクロホス(pyraclofos)、ピリプロキシフェン(pyriproxyfen)、ロテノン(rotenone)、スルプロホス(sulprofos)、シラフルオフェン(silafluofen)、スピノサド(spinosad)、スルホテップ(sulfotep)、テブフェノジド(tebfenozide)、テフルベンズロン(teflubenzuron)、テフルトリン(tefluthorin)、テルブホス(terbufos)、テトラクロロビンホス(tetrachlorvinphos)、チアクロプリド(thiacloprid)、チオシクラム(thiocyclam)、チオジカルブ(thiodicarb)、チアメトキサム(thiamethoxam)、チオファノックス(thiofanox)、チオメトン(thiometon)、トルフェンピラド(tolfenpyrad)、トラロメスリン(tralomethrin)、トリクロルホン(trichlorfon)、トリアズロン(triazuron)、トリフルムロン(triflumuron)、バミドチオン(vamidothion)及びエチオン(ethion)。
【0021】
〔2〕 上記〔1〕記載の式(1)で表されるアクリロニトリル化合物の1種以上と、以下の化合物群Bより選ばれる化合物の1種以上を含有する殺ダニ組成物。
【0022】
化合物群B:アセキノシル、ブロモプロピレート、チノメチオネート、ジコフォール、エトキサゾール、フェンブタチンオキシド、ミルベメクチン、プロパルギット、ピリダベン、アバメクチン、アルディカルブ、クロルピリフォス、ジフルベンズロン、クロルフェナピル、フェントエート、エマメクチンベンゾエート、メチダチオン、オキサミル、カルシウムポリスルフィド、マンコゼブ、マンネブ及びエチオン。
【0023】
〔3〕 ハダニ、フシダニ又はホコリダニの防除に用いる上記〔2〕記載の殺ダニ組成物。
【0024】
〔4〕 上記〔1〕記載の式(1)で表されるアクリロニトリル化合物の1種以上と、上記〔1〕記載の化合物群Aより選ばれる化合物の1種以上を同時に、又は近接して処理することを特徴とする、害虫又は病害の防除方法。
【0025】
〔5〕 上記〔1〕記載の式(1)で表されるアクリロニトリル化合物の1種以上と、上記〔2〕記載の化合物群Bより選ばれる化合物の1種以上を同時に、又は近接して処理することを特徴とする、ダニの防除方法。
【0026】
〔6〕 上記〔1〕記載の式(1)で表されるアクリロニトリル化合物の1種以上と、上記〔2〕記載の化合物群Bより選ばれる化合物の1種以上を同時に、又は近接して処理することを特徴とする、ハダニ、フシダニ又はホコリダニの防除方法。
【0027】
【発明の実施の形態】
本発明組成物及び本発明方法における一方の有効成分化合物である式(1)で表されるアクリロニトリル化合物の−C(CN)=C(OB)−部は、E体およびZ体の2種の異性体が存在するが、両者とも本発明に含まれる。
【0028】
本発明組成物及び本発明方法における一方の有効成分化合物であるアクリロニトリル化合物は、式(1)中の置換基Bが水素原子の場合、下式で表される互変異性形で存在しうることは理解されるであろう。
【0029】
【化13】
Figure 2004155693
【0030】
該化合物は主としてエノール形(1′)で存在すると考えられるが、或条件下では互変異性形(2)およびエキソオレフィン形(2′)をとりうる。本発明は3つの互変異性形およびそれらの混合物を全て包含すると理解されるべきである。
【0031】
本発明組成物に含有される又は本発明方法で使用される一方の有効成分である式(1)で表されるアクリロニトリル化合物は、作用性が従来の有機塩素系殺虫剤、有機リン系殺虫剤、カーバメート系殺虫剤およびピレスロイド系殺虫剤などの薬剤とは異なるものであり、またある種の害虫に対しては低薬量で死にいたらしめるとともに残効性も備え、結果的に顕著な防除効果を発揮するものである。加えて、式(1)で表されるアクリロニトリル化合物は、ある種の病害に対し低薬量で予防活性、あるいは治病活性を示し、結果的に顕著な防除効果を発揮するものである。しかしながら、いうまでもなくこの式(1)で表されるアクリロニトリル化合物のみを使用することで全ての分野の全ての害虫、あるいは病害を防除することは不可能である。
【0032】
本発明の式(1)で表されるアクリロニトリル化合物の中で、殺虫、殺ダニ又は殺線虫効果が高く、かつ哺乳動物、魚類および天敵等の有用生物に対して悪影響が少ない点で好ましい化合物は、以下の第1表に示す化合物である。尚、第1表中の略号はそれぞれ以下の意味を示す。
【0033】
Me:メチル基、Et:エチル基、Pr:プロピル基、Bu:ブチル基、Ph:フェニル基、i:イソ、t:ターシャリー。
【0034】
また、第1表中の置換基Aの略号はそれぞれ以下の意味を示す。
【0035】
【化14】
Figure 2004155693
【0036】
〔第1表〕
【0037】
【化15】
Figure 2004155693
【0038】
【表1】
Figure 2004155693
Figure 2004155693
【0039】
また、式(1)で表されるアクリロニトリル化合物と共に用いられる、もう一方の有効成分化合物は、殺虫、殺ダニ、殺線虫、殺菌又は殺バクテリア化合物として公知のものであり、以下の第2表に化合物No.と共に示す。そして、これらの化合物には抵抗性害虫あるいは耐性菌の出現、更に殺虫殺菌スペクトラムや残効性の不足により、薬剤の散布薬量、散布回数が増加する傾向にあり、防除効果のみならず、人畜あるいは水生生物に対する危険性の増加など、環境安全性の面からも改善が求められているものもある。
【0040】
【表2】
Figure 2004155693
Figure 2004155693
Figure 2004155693
Figure 2004155693
Figure 2004155693
【0041】
本発明組成物及び本発明方法の特徴は、第1に、各薬剤の単独での施用の場合に比べ、その殺虫、殺ダニ、殺線虫、殺菌又は殺バクテリア効力が明らかに増強されるとともに、即効的な殺虫、殺ダニ、殺線虫、殺菌又は殺バクテリア効果が付与されることである。第2に、既存の殺虫、殺ダニ、殺線虫、殺菌又は殺バクテリア剤に観られない広い殺虫、殺ダニ、殺線虫、殺菌又は殺バクテリアスペクトラムや、長い残効性が誘導されることである。第3に、各薬剤を単独で使用した場合に比べ、投下薬量を低下させうることである。
【0042】
即ち、本発明組成物及び本発明方法は、相乗的殺虫、殺ダニ、殺線虫、殺菌又は殺バクテリア効果を奏するものである。この相乗的殺虫、殺ダニ、殺線虫、殺菌又は殺バクテリア効果は、各単剤の有する殺虫、殺ダニ、殺線虫、殺菌又は殺バクテリア効果からは予測し得ぬものであり、本発明組成物及び本発明方法の有用性は各種病害虫に対して各化合物を単独で使用するよりも確実な防除効果を発揮し得る点にあるといえる。
【0043】
上記の第2表に示した化合物の中で、式(1)で表されるアクリロニトリル化合物と組み合わせることにより、特にダニに対する防除効果が、相乗的により向上する化合物を、以下の第3表に示す。
【0044】
【表3】
Figure 2004155693
【0045】
次に、相乗的病害虫防除効果を奏する化合物の組合せの具体例を以下に挙げる。以下の表記において、例えば「1+a」は、第1表のNo.1の化合物と、第2表のNo.aのアシヘ゛ンソ゛ラル−S−メチルの組合せを表している。
【0046】
化合物の組合せの例:1+a,1+b,1+c,1+d,1+e,1+f,1+g,1+h,1+i,1+j,1+k,1+l,1+m,1+n,1+o,1+p,1+q,1+r,1+s,1+t,1+u,1+v,1+w,1+x,1+y,1+z,1+aa,1+ab,1+ac,1+ad,1+ae,1+af,1+ag,1+ah,1+ai,1+aj,1+ak,1+al,1+am,1+an,1+ao,1+ap,1+aq,1+ar,1+as,1+at,1+au,1+av,1+aw,1+ax,1+ay,1+az,1+ba,1+bb,1+bc,1+bd,1+be,1+bf,1+bg,1+bh,1+bi,1+bj,1+bk,1+bl,1+bm,1+bn,1+bo,1+bp,1+bq,1+br,1+bs,1+bt,1+bu,1+bv,1+bw,1+bx,1+by,1+bz,1+ca,1+cb,1+cc,1+cd,1+ce,1+cf,1+cg,1+ch,1+ci,1+cj,1+ck,1+cl,1+cm,1+cn,1+co,1+cp,1+cq,1+cr,1+cs,1+ct,1+cu,1+cv,1+cw,1+cx,1+cy,1+cz,1+da,1+db,1+dc,1+dd,1+de,1+df,1+dg,1+dh,1+di,1+dj,1+dk,1+dl,1+dm,1+dn,1+do,1+dp,1+dq,1+dr,1+ds,1+dt,1+du,1+dv,1+dw,1+dx,1+dy,1+dz,1+ea,1+eb,1+ec,1+ed,1+ee,1+ef,1+eg,1+eh,1+ei,1+ej,1+ek,1+el,1+em,1+en,1+eo,1+ep,1+eq,1+er,1+es,1+et,1+eu,1+ev,1+ew,1+ex,1+ey,1+ez,1+fa,1+fb,1+fc,1+fd,1+fe,1+ff,1+fg,1+fh,1+fi,1+fj,1+fk,1+fl,1+fm,1+fn,1+fo,1+fp,1+fq,1+fr,1+fs,1+ft,1+fu,1+fv,1+fw,1+fx,1+fy,1+fz,1+ga,1+gb,1+gc,1+gd,1+ge,1+gf,1+gg,1+gh,1+gi,1+gj,1+gk,1+gl,1+gm,1+gn,1+go,1+gp,1+gq,1+gr,1+gs,1+gt,1+gu,1+gv,1+gw,1+gx,1+gy,1+gz,1+ha,1+hb,1+hc,1+hd,1+he,1+hf,1+hg,1+hh,1+hi,1+hj,1+hk,1+hl,1+hm,1+hn,1+ho,1+hp,1+hq,1+hr,1+hs,1+ht,1+hu,1+hv,1+hw,1+hx,1+hy,1+hz,1+ia,1+ib,1+ic,1+id,1+ie,1+if,1+ig,1+ih,1+ii,1+ij,1+ik,1+il,1+im,1+in,1+io,1+ip,1+iq,1+ir,1+is,1+it,1+iu,1+iv,1+iw,1+ix,1+iy,1+iz,1+ja,1+jb,1+jc,1+jd,1+je,1+jf,1+jg,1+jh,1+ji,1+jj,1+jk,1+jl,1+jm,1+jn,1+jo,1+jp,1+jq,1+jr,1+js,1+jt,1+ju,1+jv,1+jw,1+jx,1+jy,1+jz,1+ka,1+kb,1+kc,1+kd,1+ke,1+kf,1+kg,1+kh,1+ki,1+kj,1+kk,1+kl,1+km,1+kn,1+ko,1+kp,1+kq,1+kr,1+ks,1+kt,1+ku,1+kv,1+kw,1+kx,1+ky,1+kz,1+la,1+lb,1+lc,1+ld,1+le,1+lf,1+lg,1+lh,1+li,1+lj,1+lk,1+ll,1+lm,1+ln,1+lo,1+lp,1+lq,1+lr,1+ls,1+lt,1+lu,1+lv,1+lw,1+lx,1+ly,2+a,2+b,2+c,2+d,2+e,2+f,2+g,2+h,2+i,2+j,2+k,2+l,2+m,2+n,2+o,2+p,2+q,2+r,2+s,2+t,2+u,2+v,2+w,2+x,2+y,2+z,2+aa,2+ab,2+ac,2+ad,2+ae,2+af,2+ag,2+ah,2+ai,2+aj,2+ak,2+al,2+am,2+an,2+ao,2+ap,2+aq,2+ar,2+as,2+at,2+au,2+av,2+aw,2+ax,2+ay,2+az,2+ba,2+bb,2+bc,2+bd,2+be,2+bf,2+bg,2+bh,2+bi,2+bj,2+bk,2+bl,2+bm,2+bn,2+bo,2+bp,2+bq,2+br,2+bs,2+bt,2+bu,2+bv,2+bw,2+bx,2+by,2+bz,2+ca,2+cb,2+cc,2+cd,2+ce,2+cf,2+cg,2+ch,2+ci,2+cj,2+ck,2+cl,2+cm,2+cn,2+co,2+cp,2+cq,2+cr,2+cs,2+ct,2+cu,2+cv,2+cw,2+cx,2+cy,2+cz,2+da,2+db,2+dc,2+dd,2+de,2+df,2+dg,2+dh,2+di,2+dj,2+dk,2+dl,2+dm,2+dn,2+do,2+dp,2+dq,2+dr,2+ds,2+dt,2+du,2+dv,2+dw,2+dx,2+dy,2+dz,2+ea,2+eb,2+ec,2+ed,2+ee,2+ef,2+eg,2+eh,2+ei,2+ej,2+ek,2+el,2+em,2+en,2+eo,2+ep,2+eq,2+er,2+es,2+et,2+eu,2+ev,2+ew,2+ex,2+ey,2+ez,2+fa,2+fb,2+fc,2+fd,2+fe,2+ff,2+fg,2+fh,2+fi,2+fj,2+fk,2+fl,2+fm,2+fn,2+fo,2+fp,2+fq,2+fr,2+fs,2+ft,2+fu,2+fv,2+fw,2+fx,2+fy,2+fz,2+ga,2+gb,2+gc,2+gd,2+ge,2+gf,2+gg,2+gh,2+gi,2+gj,2+gk,2+gl,2+gm,2+gn,2+go,2+gp,2+gq,2+gr,2+gs,2+gt,2+gu,2+gv,2+gw,2+gx,2+gy,2+gz,2+ha,2+hb,2+hc,2+hd,2+he,2+hf,2+hg,2+hh,2+hi,2+hj,2+hk,2+hl,2+hm,2+hn,2+ho,2+hp,2+hq,2+hr,2+hs,2+ht,2+hu,2+hv,2+hw,2+hx,2+hy,2+hz,2+ia,2+ib,2+ic,2+id,2+ie,2+if,2+ig,2+ih,2+ii,2+ij,2+ik,2+il,2+im,2+in,2+io,2+ip,2+iq,2+ir,2+is,2+it,2+iu,2+iv,2+iw,2+ix,2+iy,2+iz,2+ja,2+jb,2+jc,2+jd,2+je,2+jf,2+jg,2+jh,2+ji,2+jj,2+jk,2+jl,2+jm,2+jn,2+jo,2+jp,2+jq,2+jr,2+js,2+jt,2+ju,2+jv,2+jw,2+jx,2+jy,2+jz,2+ka,2+kb,2+kc,2+kd,2+ke,2+kf,2+kg,2+kh,2+ki,2+kj,2+kk,2+kl,2+km,2+kn,2+ko,2+kp,2+kq,2+kr,2+ks,2+kt,2+ku,2+kv,2+kw,2+kx,2+ky,2+kz,2+la,2+lb,2+lc,2+ld,2+le,2+lf,2+lg,2+lh,2+li,2+lj,2+lk,2+ll,2+lm,2+ln,2+lo,2+lp,2+lq,2+lr,2+ls,2+lt,2+lu,2+lv,2+lw,2+lx,2+ly,3+a,3+b,3+c,3+d,3+e,3+f,3+g,3+h,3+i,3+j,3+k,3+l,3+m,3+n,3+o,3+p,3+q,3+r,3+s,3+t,3+u,3+v,3+w,3+x,3+y,3+z,3+aa,3+ab,3+ac,3+ad,3+ae,3+af,3+ag,3+ah,3+ai,3+aj,3+ak,3+al,3+am,3+an,3+ao,3+ap,3+aq,3+ar,3+as,3+at,3+au,3+av,3+aw,3+ax,3+ay,3+az,3+ba,3+bb,3+bc,3+bd,3+be,3+bf,3+bg,3+bh,3+bi,3+bj,3+bk,3+bl,3+bm,3+bn,3+bo,3+bp,3+bq,3+br,3+bs,3+bt,3+bu,3+bv,3+bw,3+bx,3+by,3+bz,3+ca,3+cb,3+cc,3+cd,3+ce,3+cf,3+cg,3+ch,3+ci,3+cj,3+ck,3+cl,3+cm,3+cn,3+co,3+cp,3+cq,3+cr,3+cs,3+ct,3+cu,3+cv,3+cw,3+cx,3+cy,3+cz,3+da,3+db,3+dc,3+dd,3+de,3+df,3+dg,3+dh,3+di,3+dj,3+dk,3+dl,3+dm,3+dn,3+do,3+dp,3+dq,3+dr,3+ds,3+dt,3+du,3+dv,3+dw,3+dx,3+dy,3+dz,3+ea,3+eb,3+ec,3+ed,3+ee,3+ef,3+eg,3+eh,3+ei,3+ej,3+ek,3+el,3+em,3+en,3+eo,3+ep,3+eq,3+er,3+es,3+et,3+eu,3+ev,3+ew,3+ex,3+ey,3+ez,3+fa,3+fb,3+fc,3+fd,3+fe,3+ff,3+fg,3+fh,3+fi,3+fj,3+fk,3+fl,3+fm,3+fn,3+fo,3+fp,3+fq,3+fr,3+fs,3+ft,3+fu,3+fv,3+fw,3+fx,3+fy,3+fz,3+ga,3+gb,3+gc,3+gd,3+ge,3+gf,3+gg,3+gh,3+gi,3+gj,3+gk,3+gl,3+gm,3+gn,3+go,3+gp,3+gq,3+gr,3+gs,3+gt,3+gu,3+gv,3+gw,3+gx,3+gy,3+gz,3+ha,3+hb,3+hc,3+hd,3+he,3+hf,3+hg,3+hh,3+hi,3+hj,3+hk,3+hl,3+hm,3+hn,3+ho,3+hp,3+hq,3+hr,3+hs,3+ht,3+hu,3+hv,3+hw,3+hx,3+hy,3+hz,3+ia,3+ib,3+ic,3+id,3+ie,3+if,3+ig,3+ih,3+ii,3+ij,3+ik,3+il,3+im,3+in,3+io,3+ip,3+iq,3+ir,3+is,3+it,3+iu,3+iv,3+iw,3+ix,3+iy,3+iz,3+ja,3+jb,3+jc,3+jd,3+je,3+jf,3+jg,3+jh,3+ji,3+jj,3+jk,3+jl,3+jm,3+jn,3+jo,3+jp,3+jq,3+jr,3+js,3+jt,3+ju,3+jv,3+jw,3+jx,3+jy,3+jz,3+ka,3+kb,3+kc,3+kd,3+ke,3+kf,3+kg,3+kh,3+ki,3+kj,3+kk,3+kl,3+km,3+kn,3+ko,3+kp,3+kq,3+kr,3+ks,3+kt,3+ku,3+kv,3+kw,3+kx,3+ky,3+kz,3+la,3+lb,3+lc,3+ld,3+le,3+lf,3+lg,3+lh,3+li,3+lj,3+lk,3+ll,3+lm,3+ln,3+lo,3+lp,3+lq,3+lr,3+ls,3+lt,3+lu,3+lv,3+lw,3+lx,3+ly,4+a,4+b,4+c,4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,43+hv,43+hw,43+hx,43+hy,43+hz,43+ia,43+ib,43+ic,43+id,43+ie,43+if,43+ig,43+ih,43+ii,43+ij,43+ik,43+il,43+im,43+in,43+io,43+ip,43+iq,43+ir,43+is,43+it,43+iu,43+iv,43+iw,43+ix,43+iy,43+iz,43+ja,43+jb,43+jc,43+jd,43+je,43+jf,43+jg,43+jh,43+ji,43+jj,43+jk,43+jl,43+jm,43+jn,43+jo,43+jp,43+jq,43+jr,43+js,43+jt,43+ju,43+jv,43+jw,43+jx,43+jy,43+jz,43+ka,43+kb,43+kc,43+kd,43+ke,43+kf,43+kg,43+kh,43+ki,43+kj,43+kk,43+kl,43+km,43+kn,43+ko,43+kp,43+kq,43+kr,43+ks,43+kt,43+ku,43+kv,43+kw,43+kx,43+ky,43+kz,43+la,43+lb,43+lc,43+ld,43+le,43+lf,43+lg,43+lh,43+li,43+lj,43+lk,43+ll,43+lm,43+ln,43+lo,43+lp,43+lq,43+lr,43+ls,43+lt,43+lu,43+lv,43+lw,43+lx,43+ly.
【0047】
本発明組成物及び本発明方法における式(1)で表される化合物と、化合物群Aから選ばれる化合物との好適な混合割合は、式(1)で表される化合物の1重量部に対して、化合物群Aから選ばれる化合物は通常0.001〜1000重量部、好ましくは0.01〜100重量部、より好ましくは0.1〜10重量部である。
【0048】
本発明組成物及び本発明方法における有効成分化合物の好ましい処理量は、防除すべき対象病害虫の種類などにより左右されるが、通常式(1)で表される化合物が0.1〜1000gai/ha、化合物群Aから選ばれる化合物が0.1〜1000gai/haであり、好ましくは前者が1〜300gai/haであり、後者が1〜300gai/haである。
【0049】
本発明組成物は、農園芸作物および樹木などを加害するいわゆる農業害虫、農業病害、家畜家禽類に寄生するいわゆる家畜害虫、家屋等の人間の生活環境で悪影響を与えるいわゆる衛生害虫、および同様の場面で発生加害するダニ類や線虫類に対して適用できる。本発明組成物を用いて防除しうる害虫、ダニ類、線虫類、病害には具体的には次に示すものがあるが、それらのみに限定されるものではない。
【0050】
害虫としては、ハスモンヨトウ(Spodoptera litura)、コブノメイガ(Cnaphalocrocis medinalis)、コナガ(Plutella xylostella)、ヨトウガ(Mamestra brassicae)、モンシロチョウ(Pieris rapae crucivora)、カブラヤガ(Agrotis segetum)、チャノコカクモンハマキ(Adoxophyes sp.)、チャハマキ(Homona magnanima)、タバコバットワーム(Heliothis virescens)、ヨーロピアンコーンボーラー(Ostrinia nubilalis)、フォールアーミーワーム(Spodoptera frugiperda)、コーンイヤーワーム(Helicoverpa zea)などの鱗翅目害虫、ツマグロヨコバイ(Nephotettix cincticeps)、トビイロウンカ(Nilaparvata lugens)、モモアカアブラムシ(Myzus persicae)、クサギカメムシ(Halyomorpha mista)、トコジラミ(Cimex lectularius)などの半翅目害虫、ニジュウヤホシテントウ(Epilachna vigintioctpunctata)、ドウガネブイブイ(Anomala cuprea)、イネミズゾウムシ(Lissorhopterus oryzophilus)、サザンコーンルートワーム(、ノーザンコーンルートワーム(Diabrotica barberi)、ウェスタンコーンルートワーム(Diabrotica virgifera virgifera)、ココクゾウ(Sitophilus oryzae)などの鞘翅目害虫、イエバエ(Musca domestica)、アカイエカ(Culex pipiens pallens)、マメハモグリバエ(Liriomyza trifolii)、ウリミバエ(Dacus cucurbitae)などの双翅目害虫、ミナミキイロアザミウマ(Thrips palmi)、ネギアザミウマ(Thrips tabaci)、ミカンキイロアザミウマ(Frankliniella occidentalis)などの総翅目害虫、ネコノミ(Ctenocephalidae felis)、ケオプスネズミノミ(Xenopsylla cheopis)、などの等翅目害虫、ニワトリオオハジラミ(Menacanthus stramineus)、ウシハジラミ(Bovicola bovis)などのハジラミ目害虫、ウシジラミ(Haematopinus eurysternus)、ウシホソジラミ(Linognathus vituli)などのシラミ目害虫、ミカンハダニ(Panonychus citri)、ナミハダニ(Tetranychus urticae)、カンザワハダニ(Tetranychus kanzawai)などのハダニ類、ミカンサビダニ(Aculops pelekassi)、チャノナガサビダニ(Acaphylla theavagrans)などのフシダニ類、チャノホコリダニ(Polyphagotarsonemus latus)、シクラメンホコリダニ(Steneotarsonemus pallidus)などのホコリダニ類、ケナガコナダニ(Tyrophagus putrescentiae)、ロビンネダニ(Rhizoglyphus robini)などのコナダニ類、オウシマダニ(Boophilusmicroplus)、フタトゲチマダニなどのマダニ類、ウサギキュウセンダニ(Psoroptes cuniculi)、ヒツジキュウセンダニ(Psoroptes ovis)などのキュウセンダニ類、ヒゼンダニ(Sarcoptes scabiei)などのヒゼンダニ類、サツマイモネコブセンチュウ(Meloidogyne javanica)、キタネグサレセンチュウ(Pratylenchus penetrans)およびジャガイモシストセンチュウ(Globodera rostochiensis)などの線虫類などが挙げられる。
【0051】
一方、病害としては、イネのいもち病(Pyricularia oryzae)、ごま葉枯病(Cochliobolus miyabeanus)、紋枯病(Rhizoctonia solani)、ムギ類のうどんこ病(Erysiphe graminis f.sp.hordei, f.sp.tritici)、斑葉病(Pyrenophoragraminea)、網斑病(Pyrenophora teres)、赤かび病(Gibberella zeae)、さび病(Puccinia striiformis, P.graminis, P.recondita, P.hordei)、雪腐病(Tipula sp., Micronectriella nivais)、裸黒穂病(Ustilago tritici, U.nuda)、アイスポット(Pseudocercosporella herpotrichoides)、雲形病(Rhynchosporium secalis)、葉枯病(Septoria tritici)、ふ枯病(Leptosphaeria nodorum)、カンキツの黒点病(Diaporthe citri)、そうか病(Elsinoe fawcetti)、果実腐敗病(Penicillium digitalum, P.italicum)、リンゴのモニリア病(Selerotinia mali)、腐らん病(Valsa mali)、うどんこ病(Podosphaera lcucotricha)、斑点落葉病(Alternaria mali)、黒星病(Venturia inaequalis)、ナシの黒星病(Venturia nashicola)、黒斑病(Alternaria kikuchiana)、赤星病(Gymnosporangium haracanum)、モモの灰星病(Sclerolinia cinerea)、黒星病(Cleadosporium carpophilum)、フォモプシス腐敗病(Phomopsis sp.)、ブドウのべと病(Plasmopara viticola)、黒とう病(Elsinoe ampelina)、晩腐病(Glomerella cingulata)、うどんこ病(Uncinula necator)、さび病(Phakopsora ampelopsidis)、カキの炭そ病(Gloeosporium kakj)、落葉病(Cercospora kakj,Mycosphaerella nawae)、ウリ類のべと病(Pseudoperenospora cubensis)、炭そ病(Colletotrichum lagenarium)、うどんこ病(Sphaerotheca fuliginea)、つる枯病(Mycosphaerella melonis)、トマトの疫病(Phytophthora infestans)、輪紋病(Alternaria solani)、葉かび病(Cladosporium fulvum)、ナスの褐紋病(Phomopsis vexans)、うどんこ病(Erysiphe cichoracoarum)、アブラナ科野菜の黒斑病(Alternaria japonica)、白斑病(Cercosporella brassicae)、ネギのさび病(Puccinia allii)、ダイズの紫斑病(Cercospora kikuchii)、黒とう病(Elsinoe glycines)、黒点病(Diaporthe phaseololum)、インゲンの炭そ病(Colletotrichum lindemuthianum)、ラッカセイの黒渋病(Mycosphaerella personatum)、褐斑病(Cercospora arachidicola)、エンドウのうどんこ病(Erysiphe pisi)、ジャガイモの夏疫病(Alternaria solani)、イチゴのうどんこ病(Sphaerotheca humuli)、チャの網もち病(Exobasidium reticulatum)、白星病(Elsinoe leucospila)、タバコの赤星病(Alternaria lingipes)、うどんこ病(Erysiphe cichoracearum)、炭そ病(Colletotrichum tabacum)、テンサイの褐斑病(Cercospora beticola)、バラの黒星病(Diplocarpon rosae)、うどんこ病(Sphaerotheca pannosa)、キクの褐斑病(Septoria chrysanthemiindici)、白さび病(Puccinia horiana)、種々の作物の灰色かび病(Botrytis cinerea)および種々の作物の菌核病(Sclerotinia sclerotiorum)等が挙げられる。
【0052】
式(1)で表されるアクリロニトリル化合物と前記の第2表に示した化合物を組み合わせた場合に、本発明組成物及び本発明方法は、特にダニに対して優れた相乗効果を奏するが、ダニの中でもミカンハダニ、ナミハダニ、カンザワハダニなどのハダニ類、チャノナガサビダニ、カーネーションサビダニ、チューリップサビダニ、ミカンサビダニ、モモサビダニ、リンゴサビダニ、チャノサビダニ、ブドウサビダニ、ナシサビダニ、ニセナシサビダニなどのフシダニ類、チャノホコリダニ、シクラメンホコリダニなどのホコリダニ類に対して、より優れた相乗効果を奏する。
【0053】
本発明の式(1)で表されるアクリロニトリル化合物は、下記スキーム1に記載した方法によって合成できる。即ち、一般式(2)で表されるシアノメチルベンゼン誘導体と一般式(3)で表されるカルボン酸誘導体とを塩基存在下で反応させることにより(1)を合成することができ、更にこれを一般式(4)で表される化合物と反応させることにより式(1)で表される化合物が得られる。
〔スキーム1〕
【0054】
【化16】
Figure 2004155693
【0055】
[スキーム1中のG、A及びBは前記と同じ意味を表し、L及びLは良好な脱離基、例えば塩素原子、臭素原子、ヨウ素原子、C〜Cアルキルスルホニルオキシ、ベンゼンスルホニルオキシ、トルエンスルホニルオキシ、1−イミダゾリル及び1−ピラゾリル等である。]。
【0056】
上記の方法は塩基を用いたほうが好ましい場合もある。用いられる塩基としてはナトリウムエトキシド、ナトリウムメトキシド及びtーブトキシカリウム等のアルカリ金属アルコキシド類、水酸化ナトリウム及び水酸化カリウム等のアルカリ金属水酸化物、炭酸ナトリウム及び炭酸カリウム等のアルカリ金属炭酸塩、トリエチルアミン、ピリジン及びDBU等の有機塩基、ブチルリチウム等の有機リチウム化合物、リチウムジイソプロプロピルアミド及びリチウムビストリメチルシリルアミド等のリチウムアミド類並びに水素化ナトリウム等が挙げられる。
【0057】
上記の反応は、反応に不活性な溶媒中で行う事ができ、溶媒としてはメタノール及びエタノール等の低級アルコール類、ベンゼン及びトルエン等の芳香族炭化水素類、ジエチルエーテル、テトラヒドロフラン、1,4−ジオキサン、1,2−ジメトキシエタン及び1,2−ジエトキシエタン等のエーテル類、アセトン、メチルエチルケトン及びメチルイソブチルケトン等のケトン類、塩化メチレン、クロロホルム及び1,2−ジクロロエタン等のハロゲン化炭化水素類、ジメチルホルムアミド、ジメチルアセトアミド及び1,3−ジメチルイミダゾリジノン等のアミド類、アセトニトリル等のニトリル類、ジメチルスルホキシド並びにこれらの混合溶媒等が挙げられる。場合によっては、これらの溶媒と水との混合溶媒も用いる事ができ、テトラ−n−ブチルアンモニウムブロマイド等の4級アンモニウム塩を触媒として添加する事により好結果が得られる場合もある。反応温度は−70℃から200℃の任意の温度に設定する事が可能であり、0℃から150℃または溶媒を用いる場合には−70℃から溶媒の沸点の範囲が好ましい。塩基は反応基質の0.05から10当量を、好ましくは0.05から3当量の範囲である。
【0058】
式(1)で表される化合物は、常法により反応液から得ることができるが、式(1)で表される化合物を精製する必要が生じた場合には再結晶、カラムクロマトグラフィー等の任意の精製法によって分離、精製することができる。
【0059】
なお、式(1)で表される化合物が不斉炭素を有する場合には、式(1)で表される化合物は、光学活性な化合物(+)体、(−)体、又は両者を任意の比率で含むラセミ体の何れであってもよい。
【0060】
本発明組成物は、式(1)で表されるアクリトニトリル化合物の少なくとも1種と、化合物群Aの中から選ばれる少なくとも1種とを混合物としてそのまま使用することもできるが、通常適当な固体担体又は液体担体と混合し、更に所望により界面活性剤、浸透剤、展着剤、増粘剤、凍結防止剤、結合剤、固結防止剤、崩壊剤、消泡剤、防腐剤および分解防止剤等を添加して、液剤(soluble concentrate)、乳剤(emulsifiable concentrate)、水和剤(wettable powder)、水溶剤(water soluble powder)、顆粒水和剤(water dispersible granule)、顆粒水溶剤(water soluble granule)、懸濁剤(suspension concentrate)、乳濁剤(concentrated emulsion)、サスポエマルジョン(suspoemulsion)、マイクロエマルジョン(microemulsion)、粉剤(dustable powder)、粒剤(granule)およびゲル剤(gel)等任意の剤型の製剤にて実用に供することができる。また、省力化および安全性向上の観点から、上記任意の剤型の製剤を、水溶性カプセルおよび水溶性フィルムの袋等の水溶性包装体に封入して供することもできる。
【0061】
固体担体としては、例えば石英、カオリナイト、パイロフィライト、セリサイト、タルク、ベントナイト、酸性白土、アタパルジャイト、ゼオライトおよび珪藻土等の天然鉱物質類、炭酸カルシウム、硫酸アンモニウム、硫酸ナトリウムおよび塩化カリウム等の無機塩類、合成シリカならびに合成シリケートが挙げられる。
【0062】
液体担体としては、例えばエチレングリコール、プロピレングリコールおよびイソプロパノール等のアルコール類、キシレン、アルキルベンゼンおよびアルキルナフタレン等の芳香族炭化水素類、ブチルセロソルブ等のエーテル類、シクロヘキサノン等のケトン類、γ−ブチロラクトン等のエステル類、N−メチルピロリドンおよびN−オクチルピロリドン等の酸アミド類、大豆油、ナタネ油、綿実油およびヒマシ油等の植物油ならびに水が挙げられる。
【0063】
これら固体および液体担体は、単独で用いても2種以上を併用してもよい。
【0064】
界面活性剤としては、例えばポリオキシエチレンアルキルエーテル、ポリオキシエチレンアルキルアリールエーテル、ポリオキシエチレンスチリルフェニルエーテル、ポリオキシエチレンポリオキシプロピレンブロックコポリマー、ポリオキシエチレン脂肪酸エステル、ソルビタン脂肪酸エステルおよびポリオキシエチレンソルビタン脂肪酸エステル等のノニオン性界面活性剤、アルキル硫酸塩、アルキルベンゼンスルホン酸塩、リグニンスルホン酸塩、アルキルスルホコハク酸塩、ナフタレンスルホン酸塩、アルキルナフタレンスルホン酸塩、ナフタレンスルホン酸のホルマリン縮合物の塩、アルキルナフタレンスルホン酸のホルマリン縮合物の塩、ポリオキシエチレンアルキルアリールエーテル硫酸および燐酸塩、ポリオキシエチレンスチリルフェニルエーテル硫酸および燐酸塩、ポリカルボン酸塩およびポリスチレンスルホン酸塩等のアニオン性界面活性剤、アルキルアミン塩およびアルキル4級アンモニウム塩等のカチオン性界面活性剤ならびにアミノ酸型およびベタイン型等の両性界面活性剤が挙げられる。
【0065】
これら界面活性剤の含有量は、特に限定されるものではないが、本発明の製剤100重量部に対し、通常0.05〜20重量部の範囲が望ましい。また、これら界面活性剤は、単独で用いても2種以上を併用してもよい。
【0066】
次に本発明組成物を用いる場合の製剤の配合例を示す。但し本発明の配合例は、これらのみに限定されるものではない。なお、以下の配合例において「部」は重量部を意味する。
【0067】
〔水和剤(wettable powder)〕
有効成分化合物 0.1〜80部
固体担体 5〜98.9部
界面活性剤 1〜10部
その他 0〜 5部
その他として、例えば固結防止剤、分解防止剤等があげれらる。
【0068】
〔乳 剤(emulsifiable concentrate)〕
有効成分化合物 0.1〜30部
液体担体 45〜95部
界面活性剤 4.9〜15部
その他 0〜10部
その他として、例えば展着剤、分解防止剤等が挙げられる。
【0069】
〔懸濁剤(suspension concentrate)〕
有効成分化合物 0.1〜70部
液体担体 15〜98.89部
界面活性剤 1〜12部
その他 0.01〜30部
その他として、例えば凍結防止剤、増粘剤等が挙げられる。
【0070】
〔顆粒水和剤(water dispersible granule)〕
有効成分化合物 0.1〜90部
固体担体 0〜98.9部
界面活性剤 1〜20部
その他 0〜 10部
その他として、例えば結合剤、分解防止剤等が挙げられる。
【0071】
〔液 剤(soluble concentrate)〕
有効成分化合物 0.01〜70部
液体担体 20〜99.99部
その他 0〜 10部
その他として、例えば凍結防止剤、展着剤等が挙げられる。
【0072】
〔粒 剤(granule)〕
有効成分化合物 0.01〜80部
固体担体 10〜99.99部
その他 0〜10部
その他として、例えば結合剤、分解防止剤等が挙げられる。
【0073】
〔粉 剤(dustable powder)〕
有効成分化合物 0.01〜30部
固体担体 65〜99.99部
その他 0〜5部
その他として、例えばドリフト防止剤、分解防止剤等が挙げられる。
【0074】
〔製剤例〕
次に具体的に本発明組成物を有効成分とする農薬製剤例を示すがこれらのみに限定されるものではない。尚、以下の配合例において「部」は重量部を意味する。
【0075】
〔配合例1〕水和剤(wettable powder)
化合物No.1 10部
化合物No.a 10部
パイロフィライト 76部
ソルポール5039 2部
(非イオン性界面活性剤とアニオン性界面活性剤との混合物:東邦化学工業(株)商品名)
カープレックス#80D 2部
(合成含水珪酸:塩野義製薬(株)商品名)
以上を均一に混合粉砕して水和剤とする。
【0076】
〔配合例2〕乳 剤(emulsifiable concentrate)
化合物No.2 3部
化合物No.b 2部
キシレン 75部
N−メチルピロリドン 15部
ソルポール2680 5部
(非イオン性界面活性剤とアニオン性界面活性剤との混合物:東邦化学工業(株)商品名)
以上を均一に混合して乳剤とする。
【0077】
〔配合例3〕懸濁剤(suspension concentrate)
化合物No.3 15部
化合物No.c 10部
アグリゾールS−710 10部
(非イオン性界面活性剤:花王(株)商品名)
ルノックス1000C 0.5部
(アニオン性界面活性剤:東邦化学工業(株)商品名)
キサンタンガム 0.2部
水 64.3部
以上を均一に混合した後、湿式粉砕して懸濁剤とする。
【0078】
〔配合例4〕顆粒水和剤(water dispersible granule)
化合物No.4 40部
化合物No.d 35部
ハイテノールNE−15 5部
(アニオン性界面活性剤:第一工業製薬(株)商品名)
バニレックスN 10部
(アニオン性界面活性剤:日本製紙(株)商品名)
カープレックス#80D 10部
(合成含水珪酸:塩野義製薬(株)商品名)
以上を均一に混合粉砕した後、少量の水を加えて攪拌混合し、押出式造粒機で造粒し、乾燥して顆粒水和剤とする。
【0079】
〔配合例5〕粒 剤(granule)
化合物No.5 3部
化合物No.e 2部
ベントナイト 50部
タルク 45部
以上を均一に混合粉砕した後、少量の水を加えて攪拌混合し、押出式造粒機で造粒し、乾燥して粒剤とする。
【0080】
〔配合例6〕粉 剤(dustable powder)
化合物No.6 2部
化合物No.f 1部
カープレックス#80D 0.5部
(ホワイトカーボン:塩野義製薬(株)商品名)
カオリナイト 95部
リン酸ジイソプロピル 1.5部
以上を均一に混合粉砕して粉剤とする。
【0081】
使用に際しては上記水和剤、乳剤、フロアブル剤、粒状水和剤は水で50〜20000倍に希釈して有効成分が1ヘクタール(ha)当たり0.005〜50kgになるように散布する。
【0082】
【実施例】
以下に、本発明の式(1)で表されるアクリロニトリル化合物の合成例を具体的に示す。
【0083】
〔合成例1〕2−(4−クロロフェニル)−3−(1,3、4−トリメチルピラゾール−5−イル)−3−ヒドロキシ−アクリロニトリル(化合物No.1)の合成
4−クロロフェニルアセトニトリル5.0gと1,3、4−トリメチル−5−カルボニルクロリド5.69gをテトラヒドロフラン60mlに溶解し、氷冷下にてカリウム tert−ブトキサイド8.13gを加えた。室温で4時間撹拌した後、減圧下にて溶媒を留去し、残査に希塩酸を加えて酸性にした後、酢酸エチルで抽出、水洗、無水硫酸ナトリウムで乾燥後、減圧下で溶媒を留去し、析出した結晶をジイソプロピルエーテルで洗浄する事で標記目的化合物7.43gを得た。融点:219−220℃。
【0084】
〔合成例2〕2−(4−クロロフェニル)−3−ピバロイルオキシ−3−(1,3、4−トリメチルピラゾール−5−イル)アクリロニトリル(化合物No.2)の合成
2−(4−クロロフェニル)−3−(1,3、4−トリメチルピラゾール−5−イル)−3−ヒドロキシ−アクリロニトリル1.5gをテトラヒドロフラン20mlに溶解し、カリウム tert−ブトキサイド0.64gを加えた後、ピバロイルクロリド0.75gを滴下し、室温で一晩撹拌した。反応混合物を水中に注ぎ酢酸エチルで抽出、水洗、無水硫酸ナトリウムで乾燥後、減圧下で溶媒を留去して得られた油状物をジイソプロピルエーテルから結晶化する事で、標記目的化合物1.37gを得た。融点:148℃。
【0085】
上記合成例に準じて、前記の第1表に記載した式(1)で表されるアクリロニトリル化合物を合成した。合成した化合物の物性を第4表に記載した。
【0086】
【表4】
Figure 2004155693
Figure 2004155693
【0087】
次に、本発明の有用性を明らかにするため、効力試験例を具体的に以下に示す。
【0088】
〔試験例1〕 ミカンサビダニに対する効力試験
上記の第4表に記載された化合物と、前記の第3表に記載された化合物を、各々10%乳剤(化合物によっては25%水和剤)に製剤し、その製剤を展着剤の入った水で希釈して、所定濃度の薬液を調製した。次に、ミカンサビダニが寄生したみかん果実から、寄生部の果皮を切りとって小さな切片(5mm×5mm程度)を作り、クリスタルバイオレットを入れた0.3%寒天溶液を用いてシャーレ内に固定したのち、実体顕微鏡下で切片上の全てのサビダニ幼虫および必要な場合は一部の成虫を除去し、一切片あたりのサビダニ成虫数が20〜30頭となるように調整した。こうして準備した供試切片に所定濃度の薬液を各5ml散布処理し、風乾後に孔のあいた蓋をして25℃の恒温室に収容した。4日後の死虫数を調査し、下記の計算式から死虫率を算出した。尚、試験は2区制で行なった。
【0089】
死虫率(%)=死虫数/供試虫数×100
各薬液濃度に対する死虫率から、プロビット法に基づいて半数致死濃度(LC50値)を求めた。更に共力効果(相乗効果)の程度を判定するために通常用いられているSun & Johnson法(ジャーナル オブ エコノミック エントモロジー誌、1960年、第55巻、887頁)の式を用いて、共力係数を計算した。共力係数は次に示す式で表される。
【0090】
共力係数=混合剤の実際の毒性指数/混合剤の理論的毒性指数×100
但し、
混合剤の実際の毒性指数:[A]のLC50/[A][B]混合剤のLC50×100
混合剤の理論的毒性指数:([A]の毒性指数×[A][B]混合剤の中の[A]の%+[B]の毒性指数×[A][B]混合剤中の[B]の%)/100
[A]:式(1)で表されるアクリロニトリル化合物
[B]:化合物群Aから選ばれる化合物
%:[A]と[B]の総重量に対する重量百分率
[A]の毒性指数:100
[B]の毒性指数:([A]のLC50/[B]のLC50)×100
である。
【0091】
この共力係数の値が100より大きいほど相乗効果が高く、100に等しいときは相加的効果、100より小さくなるほど拮抗効果が高くなる、ということを示す。
【0092】
試験の結果、下記の化合物の組合わせにおいて、共力係数が100よりも大きくなった。
【0093】
共力係数が100よりも大きくなった化合物の組合せ:1+v,1+df,1+dg,1+gh,1+gk,1+gl,1+gp,1+gr,1+gt,1+gy,1+gz,1+ha,1+hd,1+hg,1+ht,1+hu,1+il,1+iq,1+jy,1+kl,1+kp,1+ly,2+v,2+df,2+dg,2+gh,2+gk,2+gl,2+gp,2+gr,2+gt,2+gy,2+gz,2+ha,2+hd,2+hg,2+ht,2+hu,2+il,2+iq,2+jy,2+kl,2+kp,2+ly,3+v,3+df,3+dg,3+gh,3+gk,3+gl,3+gp,3+gr,3+gt,3+gy,3+gz,3+ha,3+hd,3+hg,3+ht,3+hu,3+il,3+iq,3+jy,3+kl,3+kp,3+ly,4+v,4+df,4+dg,4+gh,4+gk,4+gl,4+gp,4+gr,4+gt,4+gy,4+gz,4+ha,4+hd,4+hg,4+ht,4+hu,4+il,4+iq,4+jy,4+kl,4+kp,4+ly,5+v,5+df,5+dg,5+gh,5+gk,5+gl,5+gp,5+gr,5+gt,5+gy,5+gz,5+ha,5+hd,5+hg,5+ht,5+hu,5+il,5+iq,5+jy,5+kl,5+kp,5+ly,6+v,6+df,6+dg,6+gh,6+gk,6+gl,6+gp,6+gr,6+gt,6+gy,6+gz,6+ha,6+hd,6+hg,6+ht,6+hu,6+il,6+iq,6+jy,6+kl,6+kp,6+ly,7+v,7+df,7+dg,7+gh,7+gk,7+gl,7+gp,7+gr,7+gt,7+gy,7+gz,7+ha,7+hd,7+hg,7+ht,7+hu,7+il,7+iq,7+jy,7+kl,7+kp,7+ly,8+v,8+df,8+dg,8+gh,8+gk,8+gl,8+gp,8+gr,8+gt,8+gy,8+gz,8+ha,8+hd,8+hg,8+ht,8+hu,8+il,8+iq,8+jy,8+kl,8+kp,8+ly,9+v,9+df,9+dg,9+gh,9+gk,9+gl,9+gp,9+gr,9+gt,9+gy,9+gz,9+ha,9+hd,9+hg,9+ht,9+hu,9+il,9+iq,9+jy,9+kl,9+kp,9+ly,10+v,10+df,10+dg,10+gh,10+gk,10+gl,10+gp,10+gr,10+gt,10+gy,10+gz,10+ha,10+hd,10+hg,10+ht,10+hu,10+il,10+iq,10+jy,10+kl,10+kp,10+ly,11+v,11+df,11+dg,11+gh,11+gk,11+gl,11+gp,11+gr,11+gt,11+gy,11+gz,11+ha,11+hd,11+hg,11+ht,11+hu,11+il,11+iq,11+jy,11+kl,11+kp,11+ly,12+v,12+df,12+dg,12+gh,12+gk,12+gl,12+gp,12+gr,12+gt,12+gy,12+gz,12+ha,12+hd,12+hg,12+ht,12+hu,12+il,12+iq,12+jy,12+kl,12+kp,12+ly,13+v,13+df,13+dg,13+gh,13+gk,13+gl,13+gp,13+gr,13+gt,13+gy,13+gz,13+ha,13+hd,13+hg,13+ht,13+hu,13+il,13+iq,13+jy,13+kl,13+kp,13+ly,14+v,14+df,14+dg,14+gh,14+gk,14+gl,14+gp,14+gr,14+gt,14+gy,14+gz,14+ha,14+hd,14+hg,14+ht,14+hu,14+il,14+iq,14+jy,14+kl,14+kp,14+ly,15+v,15+df,15+dg,15+gh,15+gk,15+gl,15+gp,15+gr,15+gt,15+gy,15+gz,15+ha,15+hd,15+hg,15+ht,15+hu,15+il,15+iq,15+jy,15+kl,15+kp,15+ly,16+v,16+df,16+dg,16+gh,16+gk,16+gl,16+gp,16+gr,16+gt,16+gy,16+gz,16+ha,16+hd,16+hg,16+ht,16+hu,16+il,16+iq,16+jy,16+kl,16+kp,16+ly,17+v,17+df,17+dg,17+gh,17+gk,17+gl,17+gp,17+gr,17+gt,17+gy,17+gz,17+ha,17+hd,17+hg,17+ht,17+hu,17+il,17+iq,17+jy,17+kl,17+kp,17+ly,18+v,18+df,18+dg,18+gh,18+gk,18+gl,18+gp,18+gr,18+gt,18+gy,18+gz,18+ha,18+hd,18+hg,18+ht,18+hu,18+il,18+iq,18+jy,18+kl,18+kp,18+ly,19+v,19+df,19+dg,19+gh,19+gk,19+gl,19+gp,19+gr,19+gt,19+gy,19+gz,19+ha,19+hd,19+hg,19+ht,19+hu,19+il,19+iq,19+jy,19+kl,19+kp,19+ly,20+v,20+df,20+dg,20+gh,20+gk,20+gl,20+gp,20+gr,20+gt,20+gy,20+gz,20+ha,20+hd,20+hg,20+ht,20+hu,20+il,20+iq,20+jy,20+kl,20+kp,20+ly,21+v,21+df,21+dg,21+gh,21+gk,21+gl,21+gp,21+gr,21+gt,21+gy,21+gz,21+ha,21+hd,21+hg,21+ht,21+hu,21+il,21+iq,21+jy,21+kl,21+kp,21+ly,22+v,22+df,22+dg,22+gh,22+gk,22+gl,22+gp,22+gr,22+gt,22+gy,22+gz,22+ha,22+hd,22+hg,22+ht,22+hu,22+il,22+iq,22+jy,22+kl,22+kp,22+ly,23+v,23+df,23+dg,23+gh,23+gk,23+gl,23+gp,23+gr,23+gt,23+gy,23+gz,23+ha,23+hd,23+hg,23+ht,23+hu,23+il,23+iq,23+jy,23+kl,23+kp,23+ly,24+v,24+df,24+dg,24+gh,24+gk,24+gl,24+gp,24+gr,24+gt,24+gy,24+gz,24+ha,24+hd,24+hg,24+ht,24+hu,24+il,24+iq,24+jy,24+kl,24+kp,24+ly,25+v,25+df,25+dg,25+gh,25+gk,25+gl,25+gp,25+gr,25+gt,25+gy,25+gz,25+ha,25+hd,25+hg,25+ht,25+hu,25+il,25+iq,25+jy,25+kl,25+kp,25+ly,26+v,26+df,26+dg,26+gh,26+gk,26+gl,26+gp,26+gr,26+gt,26+gy,26+gz,26+ha,26+hd,26+hg,26+ht,26+hu,26+il,26+iq,26+jy,26+kl,26+kp,26+ly,27+v,27+df,27+dg,27+gh,27+gk,27+gl,27+gp,27+gr,27+gt,27+gy,27+gz,27+ha,27+hd,27+hg,27+ht,27+hu,27+il,27+iq,27+jy,27+kl,27+kp,27+ly,28+v,28+df,28+dg,28+gh,28+gk,28+gl,28+gp,28+gr,28+gt,28+gy,28+gz,28+ha,28+hd,28+hg,28+ht,28+hu,28+il,28+iq,28+jy,28+kl,28+kp,28+ly,29+v,29+df,29+dg,29+gh,29+gk,29+gl,29+gp,29+gr,29+gt,29+gy,29+gz,29+ha,29+hd,29+hg,29+ht,29+hu,29+il,29+iq,29+jy,29+kl,29+kp,29+ly,30+v,30+df,30+dg,30+gh,30+gk,30+gl,30+gp,30+gr,30+gt,30+gy,30+gz,30+ha,30+hd,30+hg,30+ht,30+hu,30+il,30+iq,30+jy,30+kl,30+kp,30+ly,31+v,31+df,31+dg,31+gh,31+gk,31+gl,31+gp,31+gr,31+gt,31+gy,31+gz,31+ha,31+hd,31+hg,31+ht,31+hu,31+il,31+iq,31+jy,31+kl,31+kp,31+ly,32+v,32+df,32+dg,32+gh,32+gk,32+gl,32+gp,32+gr,32+gt,32+gy,32+gz,32+ha,32+hd,32+hg,32+ht,32+hu,32+il,32+iq,32+jy,32+kl,32+kp,32+ly,33+v,33+df,33+dg,33+gh,33+gk,33+gl,33+gp,33+gr,33+gt,33+gy,33+gz,33+ha,33+hd,33+hg,33+ht,33+hu,33+il,33+iq,33+jy,33+kl,33+kp,33+ly,34+v,34+df,34+dg,34+gh,34+gk,34+gl,34+gp,34+gr,34+gt,34+gy,34+gz,34+ha,34+hd,34+hg,34+ht,34+hu,34+il,34+iq,34+jy,34+kl,34+kp,34+ly,35+v,35+df,35+dg,35+gh,35+gk,35+gl,35+gp,35+gr,35+gt,35+gy,35+gz,35+ha,35+hd,35+hg,35+ht,35+hu,35+il,35+iq,35+jy,35+kl,35+kp,35+ly,36+v,36+df,36+dg,36+gh,36+gk,36+gl,36+gp,36+gr,36+gt,36+gy,36+gz,36+ha,36+hd,36+hg,36+ht,36+hu,36+il,36+iq,36+jy,36+kl,36+kp,36+ly,37+v,37+df,37+dg,37+gh,37+gk,37+gl,37+gp,37+gr,37+gt,37+gy,37+gz,37+ha,37+hd,37+hg,37+ht,37+hu,37+il,37+iq,37+jy,37+kl,37+kp,37+ly,38+v,38+df,38+dg,38+gh,38+gk,38+gl,38+gp,38+gr,38+gt,38+gy,38+gz,38+ha,38+hd,38+hg,38+ht,38+hu,38+il,38+iq,38+jy,38+kl,38+kp,38+ly,39+v,39+df,39+dg,39+gh,39+gk,39+gl,39+gp,39+gr,39+gt,39+gy,39+gz,39+ha,39+hd,39+hg,39+ht,39+hu,39+il,39+iq,39+jy,39+kl,39+kp,39+ly,40+v,40+df,40+dg,40+gh,40+gk,40+gl,40+gp,40+gr,40+gt,40+gy,40+gz,40+ha,40+hd,40+hg,40+ht,40+hu,40+il,40+iq,40+jy,40+kl,40+kp,40+ly,41+v,41+df,41+dg,41+gh,41+gk,41+gl,41+gp,41+gr,41+gt,41+gy,41+gz,41+ha,41+hd,41+hg,41+ht,41+hu,41+il,41+iq,41+jy,41+kl,41+kp,41+ly,42+v,42+df,42+dg,42+gh,42+gk,42+gl,42+gp,42+gr,42+gt,42+gy,42+gz,42+ha,42+hd,42+hg,42+ht,42+hu,42+il,42+iq,42+jy,42+kl,42+kp,42+ly,43+v,43+df,43+dg,43+gh,43+gk,43+gl,43+gp,43+gr,43+gt,43+gy,43+gz,43+ha,43+hd,43+hg,43+ht,43+hu,43+il,43+iq,43+jy,43+kl,43+kp,43+ly.
【0094】
【発明の効果】
本発明組成物及び本発明方法は、各種病害虫に対して優れた相乗的防除効果を奏する。[0001]
TECHNICAL FIELD OF THE INVENTION
The present invention relates to a pest control agent comprising a mixture of an acrylonitrile compound and a known insecticide, acaricide, nematicide, fungicide or an active ingredient compound of a bactericide. .
[0002]
[Prior art]
It is known that an acrylonitrile derivative is used as a pesticide or a biofouling inhibitor in water (for example, see Patent Document 1).
[0003]
Further, a composition containing an acrylonitrile derivative and a known insecticide, acaricide, and fungicide is known (for example, see Patent Document 2).
[0004]
[Patent Document 1]
WO 97/040009 pamphlet
[0005]
[Patent Document 2]
JP-A-11-124306
[0006]
[Problems to be solved by the invention]
Today, insecticides, mites and fungicides for controlling various pests such as agricultural and horticultural pests, forest pests, and sanitary pests have been widely developed, and a wide variety of drugs have been put to practical use. However, in recent years, pests have gained insecticide resistance and pathogens have acquired fungicide resistance due to the long-term use of such drugs, and as a result, there have been increasing cases where control with conventional drugs becomes difficult. Also, some of these drugs are highly toxic, and some are persisting in the environment for long periods of time, disrupting ecosystems. Therefore, development of a novel drug having not only a high pest control effect but also low toxicity and low residual has always been expected.
[0007]
However, on the other hand, considering the diversity of insects and pathogens as a group of organisms, their mode of attack, and the variety of situations in which they are affected, the mere use of these new drugs or existing known drugs alone will result in all control situations. It is very difficult to effectively control all pests. Thus, new methods of inducing higher control efficacy by properly combining a plurality of insecticides, mites, nematicides, fungicides or bactericides, and controlling difficult-to-control pests are also strongly desired. Has reached.
[0008]
[Means for Solving the Problems]
In view of such a situation, the present inventors have intensively studied to develop a pest control agent exhibiting excellent control activity and having little adverse effect on useful organisms such as mammals, fish and natural enemies. As a result, an insecticidal, acaricidal, nematicidal, sterilizing or bactericidal composition containing an acrylonitrile compound represented by the following formula (1) and a known insecticide, miticide, nematicide, sterilizing or bactericidal compound. However, the present invention has been found to exhibit excellent synergistic insecticidal, acaricidal, nematicidal, bactericidal or bactericidal effects which cannot be predicted from use alone.
[0009]
That is, the present invention relates to the following [1] or [2] composition (hereinafter, referred to as the present composition) and the control method of [3] to [6] (hereinafter, referred to as the present method). Things.
[0010]
[1] Insecticidal, acaricidal, nematicidal, bactericidal or bactericidal containing one or more acrylonitrile compounds represented by the following formula (1) and one or more compounds selected from the following compound group A: Composition.
[0011]
Equation (1):
[0012]
Embedded image
Figure 2004155693
[0013]
[Where A is
[0014]
Embedded image
Figure 2004155693
[0015]
Embedded image
Figure 2004155693
[0016]
Embedded image
Figure 2004155693
[0017]
Embedded image
Figure 2004155693
[0018]
Embedded image
Figure 2004155693
[0019]
And
B is H, CR 1 R 2 R 3 , CHR 1 R 2 , C 1 ~ C 4 Haloalkyl, tetrahydropyranyl, Si (CH 3 ) 3 , SO 2 Re, SO 2 NHRb, SO 2 NRaRb, C (S) NHRb, C (S) NRaRb, C (O) Rf, P (O) RgRh, P (S) RgRh, alkali metal, alkaline earth metal or NHRiRjRk, and G is H, halogen , C 1 ~ C 6 Alkyl, C substituted with Rc 1 ~ C 4 Alkyl, C 1 ~ C 4 Haloalkyl, C 1 ~ C 3 C optionally substituted with alkyl 3 ~ C 6 Cycloalkyl, C 1 ~ C 6 Alkoxy, C 2 ~ C 4 Alkenyloxy, C 2 ~ C 4 Alkynyloxy, C 1 ~ C 4 Haloalkoxy, C 1 ~ C 4 Alkylsulfenyl, C 1 ~ C 4 Alkylsulfinyl, C 1 ~ C 4 Alkylsulfonyl, C 2 ~ C 4 Alkenylsulfenyl, C 2 ~ C 4 Alkenylsulfinyl, C 2 ~ C 4 Alkenylsulfonyl, C 2 ~ C 4 Alkynylsulfenyl, C 2 ~ C 4 Alkynylsulfinyl, C 2 ~ C 4 Alkynylsulfonyl, C 1 ~ C 4 Haloalkylsulfenyl, C 1 ~ C 4 Haloalkylsulfinyl, C 1 ~ C 4 Haloalkylsulfonyl, C 2 ~ C 4 Haloalkenylsulfenyl, C 2 ~ C 4 Haloalkenylsulfinyl, C 2 ~ C 4 Haloalkenylsulfonyl, NO 2 , CN, -NU 1 U 2 , Naphthyl, methoxy substituted with Rc, C 2 ~ C 5 Alkoxycarbonyl, C 2 ~ C 4 Alkoxyalkyl, C 2 ~ C 4 Alkylcarbonyl, C 2 ~ C 4 Haloalkylcarbonyl, C 2 ~ C 5 Alkylcarbonyloxy, C 2 ~ C 5 Haloalkylcarbonyloxy, C 3 ~ C 7 Dialkylaminocarbonyloxy, phenyl optionally substituted with Z, phenoxy optionally substituted with Z, benzoyl optionally substituted with Z, pyridyl optionally substituted with Z, substituted with Z Pyridyloxy, thienyl optionally substituted with Z, methylenedioxy attached at adjacent substitution positions, halomethylenedioxy attached at adjacent substitution positions, and -N = CT 2 T 3 A 5- to 8-membered ring formed by 1 to 4 substituents selected from or an alkylene group bonded at an adjacent substituent position;
Y, Y 1 And Y 2 Is independently H, halogen, C 1 ~ C 4 Alkyl, C 1 ~ C 4 Haloalkyl, C 1 ~ C 4 Alkoxy, C 1 ~ C 4 Haloalkoxy, C 1 ~ C 4 Alkylsulfenyl, C 1 ~ C 4 Alkylsulfinyl, C 1 ~ C 4 Alkylsulfonyl, C 1 ~ C 4 Haloalkylsulfenyl, C 1 ~ C 4 Haloalkylsulfinyl, C 1 ~ C 4 Haloalkylsulfonyl, NO 2 Or CN, or a 5-, 6-, 7- or 8-membered ring formed by an alkylene group bonded at an adjacent substituent position;
Y 3 Is C 1 ~ C 4 Alkyl or C 1 ~ C 4 Haloalkyl,
Z is each independently halogen, C 1 ~ C 4 Alkyl, C 1 ~ C 4 Haloalkyl, C 1 ~ C 4 Alkoxy, C 1 ~ C 4 Haloalkoxy, C 1 ~ C 4 Alkylsulfenyl, C 1 ~ C 4 Alkylsulfinyl, C 1 ~ C 4 Alkylsulfonyl, C 2 ~ C 4 Alkenylsulfenyl, C 2 ~ C 4 Alkenylsulfinyl, C 2 ~ C 4 Alkenylsulfonyl, C 1 ~ C 4 Haloalkylsulfenyl, C 1 ~ C 4 Haloalkylsulfinyl, C 1 ~ C 4 Haloalkylsulfonyl, NO 2 , CN, -NU 1 U 2 And C 2 ~ C 5 1 to 5 substituents selected from alkoxycarbonyl,
R 1 , R 2 , R 3 And Ra are each independently C 1 ~ C 6 Alkyl,
Rb is H, C 1 ~ C 6 Alkyl, or T 1 Is phenyl optionally substituted with
Rc is halogen, C 1 ~ C 4 Alkyl, C 1 ~ C 4 Alkoxy and C 1 ~ C 4 Phenyl optionally substituted with one or more selected from haloalkyl,
Rd is halogen, C 1 ~ C 4 Alkyl and C 1 ~ C 4 Benzoyl optionally substituted by one or more selected from haloalkyl,
Re is C 1 ~ C 4 Alkyl, C 1 ~ C 4 Haloalkyl, or T 1 Is replaced by
Phenyl,
Rf is C 1 ~ C 20 Alkyl, C 2 ~ C 6 Alkenyl, C 1 ~ C 6 Haloalkyl, C 2 ~ C 4 Alkoxyalkyl, C 3 ~ C 6 Halocycloalkyl, C substituted with Rc 1 ~ C 4 Alkyl, C 1 ~ C 4 C optionally substituted with alkyl 3 ~ C 7 Cycloalkyl, cycloalkyl substituted with Rc, Rc and C 1 ~ C 4 Cyclopropyl substituted by alkyl, Rc and C substituted by halogen 3 ~ C 4 Cycloalkyl group, T 2 And C 1 ~ C 4 Cyclopropyl group substituted with alkyl, C substituted with Rc 2 ~ C 4 Alkenyl, C 1 ~ C 6 Alkoxy, C 1 ~ C 4 Haloalkoxy, C 2 ~ C 5 Alkenyloxy, C 1 ~ C 3 C optionally substituted with alkyl 3 ~ C 6 Cycloalkoxy, benzyloxy, COORa, -NU 1 U 2 , T 3 Optionally substituted phenyl, T 3 Optionally substituted with phenoxy, naphthyl, T 1 Pyridyl or A-1 to A-140 optionally substituted with
Rg and Rh are each independently OH, phenyl, C 1 ~ C 6 Alkyl, C 1 ~ C 6 Alkoxy or C 1 ~ C 4 Alkylsulfenyl,
Ri, Rj and Rk are each independently H, C 1 ~ C 6 Alkyl, C 1 ~ C 4 Alkenyl, C 1 ~ C 3 C which may be substituted by an alkyl group 3 ~ C 6 A 5- to 8-membered cycloalkyl group or benzyl, or two of Ri, Rj and Rk optionally containing an oxygen atom, a nitrogen atom or a sulfur atom together with the nitrogen atom to which each is attached; May form a ring group,
T 1 Is halogen, C 1 ~ C 4 Alkyl, C 1 ~ C 4 Haloalkyl or C 1 ~ C 4 Alkoxy,
T 2 Represents C which may be substituted with halogen 2 ~ C 4 Alkenyl,
T 3 Is halogen, C 1 ~ C 4 Alkyl, C 1 ~ C 4 Haloalkyl, C 1 ~ C 4 Alkoxy, C 1 ~ C 4 Haloalkoxy, C 1 ~ C 4 Alkylsulfenyl, C 1 ~ C 4 Alkylsulfinyl, C 1 ~ C 4 Alkylsulfonyl, C 1 ~ C 4 Haloalkylsulfenyl, C 1 ~ C 4 Haloalkylsulfinyl, C 1 ~ C 4 Haloalkylsulfonyl, NO 2 , CN, CHO, -NU 1 U 2 , 1 to 5 substituents arbitrarily selected from phenyl and phenoxy,
U 1 And U 2 Is independently H, C 1 ~ C 6 Represents alkyl, COORa, phenyl or benzyl, or 1 And U 2 And may form a 5- to 8-membered ring group which may contain an oxygen atom, a nitrogen atom or a sulfur atom together with the nitrogen atom bonded to
m represents the number of substituents, and is 0, 1, 2, or 3,
n represents the number of substituents, and is 0, 1, 2, 3, or 4;
p represents the number of substituents, and is 0, 1 or 2,
q represents the number of substituents and is 0 or 1. (However, when m, n and p represent an integer of 2 or more, the substituents may be the same or different from each other.)].
[0020]
Compound Group A: acibenzolar-S-methyl, acylaminobenzamide, ambabam, ampropyfos, anilazine, azaconazole, azaconazole (azoxystrobin), benalaxyl (benalaxyl), Benodaniru (benodanil), benomyl (benomyl), bench azole (benthiazole), Benzamakuriru (benzamacril), binapacryl (binapacryl), biphenyl (biphenyl), bitertanol (bitertanol), Betokisajin (Bethoxazin ), Bordeaux mixture, blasticidin-S, bromoconazole, bupirimate, butiobate, calcium polysulfide, calcium sulfide, calcium sulfide, calcium sulfide Captan, copper oxychloride, carpropamide, carbendazim, carboxin, CGA-279202, quinomethionate, clomethionionatzion, clomethionionazion, clomethionionatzion, clomethionionate, clomethionionatziona Lorfenazol, chloroneb, chlorothalonil, chlorozolinate, kufuraneb, cymoxanil, cyproconaprodazole, cyproconazole, cyproconazole, cyproconazole, cyproconazole, cyproconazole, cyproconazole, cyproconazole, cyproconazole, cyproconazole, cyproconazole, cyproconazole, cyproconazole, cyproconazole, cyproconazole, cyproconazole, cyproconazole, cyproconazole, cyproconazole, cyproconazole, cyproconazole, cyproconazole, cyproconazole, cyproconazole, cyproconazole, cyproconazole, cyproconazole, cyproconazole, cyproconazole, cyproconazole, cyproconazole, cyproconazole, cyproconazole, cyproconazole, cyproconazole, cyproconazole, cyproconazole, cyproconazole, cyproconazole, cyproconazole, cyproconazole, cyproconazole, cyproconazole). (Dazomet), debacarb, dichlorophen, diclobutrazol, diclofuranide, diclomedine, dichloran, dichloran, dichloran, dichloran hofencarb), diclocymet (diclocymet), difenoconazole (difenoconazole), Jifurumetorin (diflumetorim), dimethirimol (dimethirimol), dimethomorph (Dimethomorph), diniconazole (diniconazole), diniconazole -M (diniconazole-M), dinocap (dinocap), diphenylamine (diphenylamine ), Dipyrithione, ditarimfos, dithianon, dithianon, dodemorph, dodine, dorazine, drazoxolone, edifenphos. Epoxiconazole, etaconazole, etirimol, etridianol, etridiazole, famoxadone, fenarimol, febonaz, febconazole, febonazole, febconazole ), Fenfuram, fenhexamide, fenpiclonil, fenpropidin, fenpropimorph, fenpropimorph, fentin, ferban, ferimson rimzone, fluazinam, fludioxonil, fluoroimide, fluquinconazole, flusilazol, flusulfalum, flusulfalum, flusulfalum, flusulfalum (Folpet), fosetyl-aluminium, fveridazole, furalaxyl, furamepyr, guazatine, hexachlorobenzene ), Hexaconazole, hexexazole, imazalil, imazalil, imibenconazole, iminoctadine, isopropylcone, thioconazole, iconconide, thioconazole, iconconide, thioconazole, iconconione, iconcone, iconcone, iconectone, iconcone, iconcone, iconcone, iconcone, iconcone, iconcone, iconcone, iconcone, iconcone, iconcone, iconcone) , Iprovalicarb, kasugamycin, kresoxim-methyl, mancopper, mancozeb, manebze, menipiprime, mepanipirime (Mepronil), metalaxyl, metconazole, methasulfocarb, metiram, metiram, metominostrobin, meclobutanil, MTB, and MTB. Dimethyl dithiocarbamate) (nickel bis (dimethyldithiocarbamate)), nitrothal-isopropyl, nuarimol, NNF-9425, octylinone, oxydixyl, oxydixyl Boxin (oxycarboxin), oxpoconazole fumarate, pefurazoate, penconazole, pencicuron, potassium hydrogen, polyphthalinol, phthalide, phthalide potassium hydrogen carbonate, probenazole, prochloraz, procymidone, propamocarb hydrochloride, propacarbonechloride, propiconazole, propiconazole ropineb), pyrazophos, pyrifenox, pyrimethanil, pyroquinone, quinomethionate, quinoxyphen, sodium quinoxyne, quinoxyphene, quinoxyphen, quinoxyphen, quinoxyphene, quinoxyphene, quinoxyphene, quinoxyphene, quinoxyphene, and quinoxyphene. , Sodium hypochlorite, sulfur, spiroxamine, tebuconazole, technazene, tetraconazole, thiabendazole. bendazole), thiadiazine (thiadiazin / milneb), thifluzamide (thifluzamide), thiophanate - methyl (thiophanate-methyl), thiram (thiram), tolclofos - methyl (tolclofos-methyl), Torirufuranido (tolylfluanid), triadimefon (triadimefon), Toriajime Nori (triadimenol), triazoxide (triazoxide), tricyclazole (triclazole), tridemorph (tridemorph), triflumizole (triflumizole), trifolin (triforine), triticonazole (triticonazol) lidamycin, vinclozolin, zinc sulfate, zineb, ziram, shiitake mycelium extract, streptomycin, streptomycline, tecclophthalacyclic acid, tetraclosyl cycline, teclophthalaic acid, teclophthalacyclic acid, oxolinic acid), aldoxycarb (aldoxycarb), cadusafos (cadusafos), fosthiazate (fosthiazate), Fosuchietan (fosthietan), oxamyl (oxamyl), fenamiphos (fenamiphos), acequinocyl (acequinocyl), bromopropylate (Bromopr pyrate), chinomethionate, chlorobenzilate, cyhexatin, dicofol, dienochlor, etoxanol, etozafenxin, fenazafenuxin, fenazafenuxin, fenazafenuxin, fenazafenuxin, fenazafenuxin, fenazafenuxin, fenazafinuxin Propatrin, fenproximate, halfenprox, hexythiazox, milbemectin, propargite, pyridaben n), pyrimidifen, tebufenpyrad, abamectin, acephate, acetamipirido (acetamipirid), aldicarb (aldicarb), alesin-zal-zir-zal, alesin-alzin-alzin-alzin-alzin-alzin-alzin-alzine-alzin-alzin-alzin-alzin-alzyl-alzin-alzyl-alzin-alzyl-alzyl-alzin-alzyl-alzin-alzyl-alzin-alzyl-alzyl-alzin-alzyl-alzin-alzyl-alzyl) bendicarb, benfuracarb, bensultap, buprofezin, butocarboxim, carbaryl, carbaryl, carbofuran, carbofuran, carbofuran, carbofuran, carbofuran, carbofuran, carbofuran, carbofuran. artap), chlorfenapyr, chlorpyrifos, chlorfenvinphos, chlorfluazuron, clothianidine, clothianidominyl, clothianidominyl, clothianidomin (clothianopinomethyl) Trilin (cycloprothrin), cyfluthrin (beta-cyfluthrin), cypermethrin (cypermethrin), cyromazine (cyromazine), cyhalothrin (cyhalothrin-lamb) cyhalothrin, deltamethrin, diafenthiuron, diazinon, diacloden, diflubenzuron, dimethylvinthofino, dimethylmethosyl, dimethybento, dimethynovino, dimethybento, dimethynovino, dimethybento, dimethybento, dimethyto, dimethyto, dimethyto, dimethyto, dimethyto, dimethyto, dimethyto, dimethyto, dimethyto, dimethyto, dimethyto, dimethyto, dimethyto, dimethyto). dimethoate, emamectin-benzoate, EPN, esfenvalerate, ethiofencarb, ethiprole, etofenprox, etofenprox Trimphos, fenitrothion, fenobcarb, fenoxycarb, fenpropathrin, fenvalerate, fenprolate, fipronilate, fipronilate, fipronilate, fipronilate, fipronilate Flufenoxuron, Flufenprox, Tau-fluvalinate, phonophos, formetanate, formothion, furathiocarb urathiocarb, halofenozide, hexaflumuron, hydramethylnon, imidacloprid, isofenfos, indoxacarbocarb, indoxacarbocarboxin, and indoxacarbocarboxin. (Lufenuron), malathion (metalathion), metaldehyde (metaldehyde), methamidophos (methamidophos), methidathion (methidathion), methacrylhos (methacrifos), metalcarb (metalcarb), mesomil (methomil) myl), methoprene, methoxychlor, methoxyphenozide, monocrotophos, muscarule, nitronoteramone, nitinotefurano, nidinotefurano, nidinotefuran, nidinotefurano, nidinotefuran, nidinotefuran oxydemethon-methyl, oxamyl, parathion, parathion-methyl, permethrin, phenthoate, phoxim, phophate, phosphate Rho (phosalone), phosmet (phosmet), phosphamidon, pirimicarb, pirimiphos-methyl, profenofos, profenofo, pyrifin, pytrofine, protryfenbut, metrophene ), Pyriproxyfen, rotenone, sulprofos, silafluofen, spinosad, sulfotep, tefenofenzide, tebfentebozenbende Zuron, tefluthorin, terbufos, tetrachlorovinphos, thiacloprid, thicyclclam, thiocyclam, thiothiox, thiomethox (thiomethox), thiomethox (thiomethox). thiometon, tolfenpyrad, tralomethrin, trichlorfon, triazuron, triflumuron, triflumuron, vamidothion, and ethion.
[0021]
[2] An acaricidal composition comprising at least one acrylonitrile compound represented by the formula (1) according to the above [1] and at least one compound selected from the following compound group B.
[0022]
Compound group B: acequinosyl, bromopropylate, tinomethionate, dicophor, ethoxazole, fenbutatin oxide, milbemectin, propargite, pyridaben, abamectin, aldicarb, chlorpyrifos, diflubenzuron, chlorfenapyr, fentoate, emamectin benzoate, methidathione Polysulfide, Mancozeb, Maneb and Ethion.
[0023]
[3] The acaricidal composition according to the above [2], which is used for controlling spider mites, dust mites or dust mites.
[0024]
[4] One or more acrylonitrile compounds represented by the formula (1) described in the above [1] and one or more compounds selected from the compound group A described in the above [1] are treated simultaneously or in close proximity. A method for controlling pests or diseases.
[0025]
[5] One or more acrylonitrile compounds represented by the formula (1) described in the above [1] and one or more compounds selected from the compound group B described in the above [2] are treated simultaneously or in close proximity. A method for controlling ticks, comprising:
[0026]
[6] One or more acrylonitrile compounds represented by the formula (1) described in the above [1] and one or more compounds selected from the compound group B described in the above [2] are treated simultaneously or in close proximity. A method for controlling spider mites, dust mites or dust mites.
[0027]
BEST MODE FOR CARRYING OUT THE INVENTION
The -C (CN) = C (OB)-part of the acrylonitrile compound represented by the formula (1), which is one of the active ingredient compounds in the composition of the present invention and the method of the present invention, has two types of E-form and Z-form Although isomers exist, both are included in the present invention.
[0028]
The acrylonitrile compound, which is one of the active ingredient compounds in the composition of the present invention and the method of the present invention, can exist in a tautomeric form represented by the following formula when the substituent B in the formula (1) is a hydrogen atom. Will be understood.
[0029]
Embedded image
Figure 2004155693
[0030]
The compound is believed to exist predominantly in the enol form (1 '), but under certain conditions may take the tautomeric form (2) and the exoolefin form (2'). It is to be understood that the present invention includes all three tautomeric forms and mixtures thereof.
[0031]
The acrylonitrile compound represented by the formula (1), which is one of the active ingredients contained in the composition of the present invention or used in the method of the present invention, is a conventional organochlorine insecticide or organophosphorus insecticide having an action. It is different from drugs such as carbamate insecticides and pyrethroid insecticides, and also has a remarkable control effect with some pests being able to die at a low dose and having residual effect as a result. It demonstrates. In addition, the acrylonitrile compound represented by the formula (1) exhibits a prophylactic or curative activity at a low dose with respect to certain diseases, and consequently exerts a remarkable control effect. However, it goes without saying that it is impossible to control all pests or diseases in all fields by using only the acrylonitrile compound represented by the formula (1).
[0032]
Among the acrylonitrile compounds represented by the formula (1) of the present invention, preferred are compounds having a high insecticidal, acaricidal or nematicidal effect and having little adverse effect on useful organisms such as mammals, fish and natural enemies. Are the compounds shown in Table 1 below. The abbreviations in Table 1 have the following meanings.
[0033]
Me: methyl group, Et: ethyl group, Pr: propyl group, Bu: butyl group, Ph: phenyl group, i: iso, t: tertiary.
[0034]
The abbreviations for the substituent A in Table 1 have the following meanings.
[0035]
Embedded image
Figure 2004155693
[0036]
[Table 1]
[0037]
Embedded image
Figure 2004155693
[0038]
[Table 1]
Figure 2004155693
Figure 2004155693
[0039]
The other active ingredient compound used together with the acrylonitrile compound represented by the formula (1) is a compound known as an insecticidal, acaricidal, nematicidal, bactericidal or bactericidal compound. Compound No. Shown together. These compounds tend to increase the amount and frequency of application of chemicals due to the emergence of resistant pests or resistant bacteria and the lack of insecticidal sterilization spectrum and residual efficacy. In addition, there is a need for improvement in terms of environmental safety, such as an increase in danger to aquatic organisms.
[0040]
[Table 2]
Figure 2004155693
Figure 2004155693
Figure 2004155693
Figure 2004155693
Figure 2004155693
[0041]
The characteristics of the composition of the present invention and the method of the present invention are, firstly, that the insecticidal, acaricidal, nematicidal, bactericidal or bactericidal efficacy is clearly enhanced as compared with the case of applying each drug alone. , An immediate insecticidal, acaricidal, nematicidal, bactericidal or bactericidal effect. Second, broad insecticidal, acaricidal, nematicidal, bactericidal or bactericidal asylum not found in existing insecticides, acaricides, nematicides, bactericidal or bactericides, and long residual effects are induced. It is. Third, it is possible to reduce the dose of the administered drug as compared with the case where each drug is used alone.
[0042]
That is, the composition of the present invention and the method of the present invention have a synergistic insecticidal, acaricidal, nematicidal, bactericidal or bactericidal effect. This synergistic insecticidal, acaricidal, nematicidal, bactericidal or bactericidal effect is unpredictable from the insecticidal, acaricidal, nematicidal, bactericidal or bactericidal effect of each single agent. It can be said that the usefulness of the composition and the method of the present invention lies in that a more effective control effect can be exerted on various pests than using each compound alone.
[0043]
Among the compounds shown in Table 2 above, those compounds which, when combined with the acrylonitrile compound represented by the formula (1), have a synergistically improved control effect on ticks, in particular, are shown in Table 3 below. .
[0044]
[Table 3]
Figure 2004155693
[0045]
Next, specific examples of the combination of compounds having a synergistic pest control effect will be described below. In the following notation, for example, “1 + a” indicates No. 1 in Table 1. No. 1 in Table 2 and No. 1 in Table 2. a represents the combination of acetylbenzene-S-methyl.
[0046]
Examples of compound combinations: 1 + a, 1 + b, 1 + c, 1 + d, 1 + e, 1 + f, 1 + g, 1 + h, 1 + i, 1 + j, 1 + k, 1 + l, 1 + m, 1 + n, 1 + o, 1 + p, 1 + q, 1 + r, 1 + s, 1 + t, 1 + u, 1 + v, 1 + w, 1 + x, 1 + y, 1 + z, 1 + aa, 1 + ab, 1 + ac, 1 + ad, 1 + ae, 1 + af, 1 + ag, 1 + ah, 1 + ai, 1 + aj, 1 + ak, 1 + al, 1 + am, 1 + an, 1 + ao, 1 + ap, 1 + aq, 1 + ar, 1 + as, 1 + at, 1 + au, 1 + av, 1 + aw, 1 + ax, 1 + ay, 1 + az, 1 + ba, 1 + bb, 1 + bc, 1 + bd, 1 + be, 1 + bf, 1 + bg, 1 + bh, 1 + bi, 1 + bj, 1 + bk, 1 + bl, 1 + bm, 1 + bn, 1 + bo, 1 + bp, 1 + bq, 1 + br, 1 + bs, 1 + bt, 1 + bu, 1 + bv, 1 + bw, 1 + bx, 1 + by, 1 + bz, 1 + ca, 1 + cb, 1 + cc, 1 + cd, 1 + ce, 1 + cf, 1 + cg, 1 + ch, 1 + ci, 1 + cj, 1 + ck, 1 + cl, 1 + cm, 1 + cn, 1 + co, 1 + cp, 1 + cq, 1 + cr, 1 + cs, 1 + ct, 1 + cu, 1 + cv, 1 + cw, 1 + cx, 1 + cy, 1 + cz, 1 + da, 1 + db, 1 + dc, 1 + dd, 1 + de, 1 + df, 1 + dg, 1 + dh, 1 + di, 1 + dj, 1 + dk, 1 + dl, 1 + dm, 1 + dn, 1 + do, 1 + dp, 1 + dq, 1 + dr, 1 + ds, 1 + dt, 1 + du, 1 + dv, 1 + dw, 1 + dx, 1 + dy, 1 + dz, 1 + ea, 1 + eb, 1 + ec, 1 + ed, 1 + ee, 1 + ef, 1 + eg, 1 + eh, 1 + ei, 1 + ej, 1 + ek, 1 + el, 1 + em, 1 + en, 1 + eo, 1 + ep, 1 + eq, 1 + er, 1 + es, 1 + et, 1 + eu, 1 + ev, 1 + ew, 1 + ex, 1 + ey, 1 + ez, 1 + fa, 1 + fb, 1 + fc, 1 + fd, 1 + fe, 1 + ff, 1 + fg, 1 + fh, 1 + fi, 1 + fj, 1 + fk, 1 + fl, 1 + fm, 1 + fn, 1 + fo, 1 + fp, 1 + fq, 1 + fr, 1 + fs, 1 + ft, 1 + fu, 1 + fv, 1 + fw, 1 + fx, 1 + fy, 1 + fz, 1 + ga, 1 + gb, 1 + gc, 1 + gd, 1 + ge, 1 + gf, 1 + gg, 1 + gh, 1 + gi, 1 + gj, 1 + gk, 1 + gl, 1 + gm, 1 + gn, 1 + go, 1 + gp, 1 + gq, 1 + gr, 1 + gs, 1 + gt, 1 + gu, 1 + gv, 1 + gw, 1 + gx, 1 + gy, 1 + gz, 1 + ha, 1 + hb, 1 + hc, 1 + hd, 1 + he, 1 + hf, 1 + hg, 1 + hh, 1 + hi, 1 + hj, 1 + hk, 1 + hl, 1 + hm, 1 + hn, 1 + ho, 1 + hp, 1 + hq, 1 + hr, 1 + hs, 1 + ht, 1 + hu, 1 + hv, 1 + hw, 1 + hx, 1 + hy, 1 + hz, 1 + ia, 1 + ib, 1 + ic, 1 + id, 1 + ie, 1 + if, 1 + ig, 1 + ih, 1 + ii, 1 + ij, 1 + ik, 1 + il, 1 + im, 1 + in, 1 + io, 1 + ip, 1 + iq, 1 + ir, 1 + is, 1 + it, 1 + iu, 1 + iv, 1 + iw, 1 + ix, 1 + iy, 1 + iz, 1 + ja, 1 + jb, 1 + jc, 1 + jd, 1 + je, 1 + jf, 1 + jg, 1 + jh, 1 + ji, 1 + jj, 1 + jk, 1 + jl, 1 + jm, 1 + jn, 1 + jo, 1 + jp, 1 + jq, 1 + jr, 1 + js, 1 + jt, 1 + ju, 1 + jv, 1 + jw, 1 + jx, 1 + ji, 1 + jz, 1 + ka, 1 + kb, 1 + kc, 1 + kd, 1 + ke, 1 + kf, 1 + kg, 1 + kh, 1 + ki, 1 + kj, 1 + kk, 1 + kl, 1 + km, 1 + kn, 1 + ko, 1 + kp, 1 + kq, 1 + kr, 1 + ks, 1 + kt, 1 + ku, 1 + kv, 1 + kw, 1 + kx, 1 + ky, 1 + kz, 1 + la, 1 + lb, 1 + lc, 1 + ld, 1 + le, 1 + lf, 1 + lg, 1 + lh, 1 + li, 1 + lj, 1 + lk, 1 + 11, 1 + lm, 1 + ln, 1 + lo, 1 + lp, 1 + lq, 1 + lr, 1 + ls, 1 + lt, 1 + lu, 1 + lv, 1 + lw, 1 + lx, 1 + ly, 2 + a, 2 + b, 2 + c, 2 + d, 2 + e, 2 + f, 2 + g, 2 + h, 2 + i, 2 + j, 2 + k, 2 + l, 2 + m, 2 + n, 2 + o, 2 + p, 2 + q, 2 + r, 2 + s, 2 + t, 2 + u, 2 + v, 2 + w, 2 + x, 2 + y, 2 + z, 2 + aa, 2 + ab, 2 + ac, 2 + ad, 2 + ae, 2 + af, 2 + ag, 2 + ah, 2 + ai, 2 + aj, 2 + ak, 2 + al, 2 + am, 2 + an, 2 + ao, 2 + ap, 2 + aq, 2 + ar, 2 + as, 2 + at, 2 + au, 2 + av, 2 + aw, 2 + ax, 2 + ay, 2 + az, 2 + ba, 2 + bb, 2 + bc, 2 + bd, 2 + be, 2 + bf, 2 + bg, 2 + bh, 2 + bi, 2 + bj, 2 + bk, 2 + bl, 2 + bm, 2 + bn, 2 + bo, 2 + bp, 2 + bq, 2 + br, 2 + bs, 2 + bt, 2 + bu, 2 + bv, 2 + bw, 2 + bx, 2 + by, 2 + bz, 2 + ca, 2 + cb, 2 + cc, 2 + cd, 2 + ce, 2 + cf, 2 + cg, 2 + ch, 2 + ci, 2 + cj, 2 + ck, 2 + cl, 2 + cm, 2 + cn, 2 + co, 2 + cp, 2 + cq, 2 + cr, 2 + cs, 2 + ct, 2 + cu, 2 + cv, 2 + cw, 2 + cx, 2 + cy, 2 + cz, 2 + da, 2 + db, 2 + dc, 2 + dd, 2 + de, 2 + df, 2 + dg, 2 + dh, 2 + di, 2 + dj, 2 + dk, 2 + dl, 2 + dm, 2 + dn, 2 + do, 2 + dp, 2 + dq, 2 + dr, 2 + ds, 2 + dt, 2 + du, 2 + dv, 2 + dw, 2 + dx, 2 + dy, 2 + dz, 2 + ea, 2 + eb, 2 + ec, 2 + ed, 2 + ee, 2 + ef, 2 + eg, 2 + eh, 2 + ei, 2 + ej, 2 + ek, 2 + el, 2 + em, 2 + en, 2 + eo, 2 + ep, 2 + eq, 2 + er, 2 + es, 2 + et, 2 + eu, 2 + ev, 2 + ew, 2 + ex, 2 + ey, 2 + ez, 2 + fa, 2 + fb, 2 + fc, 2 + fd, 2 + fe, 2 + ff, 2 + fg, 2 + fh, 2 + fi, 2 + fj, 2 + fk, 2 + fl, 2 + fm, 2 + fn, 2 + fo, 2 + fp, 2 + fq, 2 + fr, 2 + fs, 2 + ft, 2 + fu, 2 + fv, 2 + fw, 2 + fx, 2 + fy, 2 + fz, 2 + ga, 2 + gb, 2 + gc, 2 + gd, 2 + ge, 2 + gf, 2 + gg, 2 + gh, 2 + gi, 2 + gj, 2 + gk, 2 + gl, 2 + gm, 2 + gn, 2 + go, 2 + gp, 2 + gq, 2 + gr, 2 + gs, 2 + gt, 2 + gu, 2 + gv, 2 + gw, 2 + gx, 2 + gy, 2 + gz, 2 + ha, 2 + hb, 2 + hc, 2 + hd, 2 + he, 2 + hf, 2 + hg, 2 + hh, 2 + hi, 2 + hj, 2 + hk, 2 + hl, 2 + hm, 2 + hn, 2 + ho, 2 + hp, 2 + hq, 2 + hr, 2 + hs, 2 + ht, 2 + hu, 2 + hv, 2 + hw, 2 + hx, 2 + hy, 2 + hz, 2 + ia, 2 + ib, 2 + ic, 2 + id, 2 + ie, 2 + if, 2 + ig, 2 + ih, 2 + ii, 2 + ij, 2 + ik, 2 + il, 2 + im, 2 + in, 2 + io, 2 + ip, 2 + iq, 2 + ir, 2 + is, 2 + it, 2 + iu, 2 + iv, 2 + iw, 2 + ix, 2 + iy, 2 + iz, 2 + ja, 2 + jb, 2 + jc, 2 + jd, 2 + je, 2 + jf, 2 + jg, 2 + jh, 2 + ji, 2 + jj, 2 + jk, 2 + jl, 2 + jm, 2 + jn, 2 + jo, 2 + jp, 2 + jq, 2 + jr, 2 + js, 2 + jt, 2 + ju, 2 + jv, 2 + jw, 2 + jx, 2 + ji, 2 + js, 2 + ka, 2 + kb, 2 + kc, 2 + kd, 2 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at, 40 + au, 40 + av, 40 + aw, 40 + ax, 40 + ay, 40 + az, 40 + ba, 40 + bb, 40 + bc, 40 + bd, 40 + be, 40 + bf, 40 + bg, 40 + bh, 40 + bi, 40 + bj, 40 + bk, 40 + bl, 40 + bm, 40 + bn, 40 + bo, 40 + bp, 40 + bq, 40 + br, 40 + bs, 40 + bt, 40 + bu, 40 + bv, 40 + bw, 40 + bx, 40 + by, 40 + bz, 40 + ca, 40 + cb, 40 + cc, 40 + cd, 40 + ce, 40 + cf, 40 + cg, 40 + ch, 40 + ci, 40 + cj, 40 + ck, 40 + cl, 40 + cm, 40 + cn, 40 + co, 40 + cp, 40 + cq, 40 + cr, 40 + cs, 40 + ct, 40 + cu, 40 + cv, 40 + cw, 40 + cx, 40 + cy, 40 + cz, 40 + da, 40 + db, 40 + dc, 40 + dd, 40 + de, 40 + df, 40 + dg, 40 + dh, 40 + di, 40 + dj, 40 + dk, 40 + dl, 40 + dm, 40 + dn, 40 + do, 40 + dp, 40 + dq, 40 + dr, 40 + ds, 40 + dt, 40 + du, 40 + dv, 40 + dw, 40 + dx, 40 + dy, 40 + dz, 40 + ea, 40 + eb, 40 + ec, 40 + ed, 40 + ee, 40 + ef, 40 + eg, 40 + eh, 40 + ei, 40 + ej, 40 + ek, 40 + el, 40 + em, 40 + en, 40 + eo, 40 + ep, 40 + eq, 40 + er, 40 + es, 40 + et, 40 + eu, 40 + ev, 40 + ew, 40 + ex, 40 + ey, 40 + ez, 40 + fa, 40 + fb, 40 + fc, 40 + fd, 40 + fe, 40 + ff, 40 + fg, 40 + fh, 40 + fi, 40 + fj, 40 + fk, 40 + fl, 40 + fm, 40 + fn, 40 + fo, 40 + fp, 40 + fq, 40 + fr, 40 + fs, 40 + ft, 40 + fu, 40 + fv, 40 + fw, 40 + fx, 40 + fy, 40 + fz, 40 + ga, 40 + gb, 40 + gc, 40 + gd, 40 + ge, 40 + gf, 40 + gg, 40 + gh, 40 + gi, 40 + gj, 40 + gk, 40 + gl, 40 + gm, 40 + gn, 40 + go, 40 + gp, 40 + gq, 40 + gr, 40 + gs, 40 + gt, 40 + gu, 40 + gv, 40 + gw, 40 + gx, 40 + gy, 40 + gz, 40 + ha, 40 + hb, 40 + hc, 40 + hd, 40 + he, 40 + hf, 40 + hg, 40 + hh, 40 + hi, 40 + hj, 40 + hk, 40 + hl, 40 + hm, 40 + hn, 40 + ho, 40 + hp, 40 + hq, 40 + hr, 40 + hs, 40 + ht, 40 + hu, 40 + hv, 40 + hw, 40 + hx, 40 + hy, 40 + hz, 40 + ia, 40 + ib, 40 + ic, 40 + id, 40 + ie, 40 + if, 40 + ig, 40 + ih, 40 + ii, 40 + ij, 40 + ik, 40 + il, 40 + im, 40 + in, 40 + io, 40 + ip, 40 + iq, 40 + ir, 40 + is, 40 + it, 40 + iu, 40 + iv, 40 + iw, 40 + ix, 40 + iy, 40 + iz, 40 + ja, 40 + jb, 40 + jc, 40 + jd, 40 + je, 40 + jf, 40 + jg, 40 + jh, 40 + ji, 40 + jj, 40 + jk, 40 + jl, 40 + jm, 40 + jn, 40 + jo, 40 + jp, 40 + jq, 40 + jr, 40 + js, 40 + jt, 40 + ju, 40 + jv, 40 + jw, 40 + jx, 40 + ji, 40 + jz, 40 + ka, 40 + kb, 40 + kc, 40 + kd, 40 + ke, 40 + kf, 40 + kg, 40 + kh, 40 + ki, 40 + kj, 40 + kk, 40 + kl, 40 + km, 40 + kn, 40 + ko, 40 + kp, 40 + kq, 40 + kr, 40 + ks, 40 + kt, 40 + ku, 40 + kv, 40 + kw, 40 + kx, 40 + ky, 40 + kz, 40 + la, 40 + lb, 40 + lc, 40 + ld, 40 + le, 40 + lf, 40 + lg, 40 + lh, 40 + li, 40 + lj, 40 + lk, 40 + 11, 40 + lm, 40 + ln, 40 + lo, 40 + lp, 40 + lq, 40 + lr, 40 + ls, 40 + lt, 40 + lu, 40 + lv, 40 + lw, 40 + lx, 40 + ly, 41 + a, 41 + b, 41 + c, 41 + d, 41 + e, 41 + f, 41 + g, 41 + h, 41 + i, 41 + j, 41 + k, 41 + 1, 41 + m, 41 + n, 41 + o, 41 + p, 41 + q, 41 + r, 41 + s, 41 + t, 41 + u, 41 + v, 41 + w, 41 + x, 41 + y, 41 + z, 41 + aa, 41 + ab, 41 + ac, 41 + ad, 41 + ae, 41 + af, 41 + ag, 41 + ah, 41 + ai, 41 + aj, 41 + ak, 41 + al, 41 + am, 41 + an, 41 + ao, 41 + ap, 41 + aq, 41 + ar, 41 + as, 41 + at, 41 + au, 41 + av, 41 + aw, 41 + ax, 41 + ay, 41 + az, 41 + ba, 41 + bb, 41 + bc, 41 + bd, 41 + be, 41 + bf, 41 + bg, 41 + bh, 41 + bi, 41 + bj, 41 + bk, 41 + bl, 41 + bm, 41 + bn, 41 + bo, 41 + bp, 41 + bq, 41 + br, 41 + bs, 41 + bt, 41 + bu, 41 + bv, 41 + bw, 41 + bx, 41 + by, 41 + bz, 41 + ca, 41 + cb, 41 + cc, 41 + cd, 41 + ce, 41 + cf, 41 + cg, 41 + ch, 41 + ci, 41 + cj, 41 + ck, 41 + cl, 41 + cm, 41 + cn, 41 + co, 41 + cp, 41 + cq, 41 + cr, 41 + cs, 41 + ct, 41 + cu, 41 + cv, 41 + cw, 41 + cx, 41 + cy, 41 + cz, 41 + da, 41 + db, 41 + dc, 41 + dd, 41 + de, 41 + df, 41 + dg, 41 + dh, 41 + di, 41 + dj, 41 + dk, 41 + dl, 41 + dm, 41 + dn, 41 + do, 41 + dp, 41 + dq, 41 + dr, 41 + ds, 41 + dt, 41 + du, 41 + dv, 41 + dw, 41 + dx, 41 + dy, 41 + dz, 41 + ea, 41 + eb, 41 + ec, 41 + ed, 41 + ee, 41 + ef, 41 + eg, 41 + eh, 41 + ei, 41 + ej, 41 + ek, 41 + el, 41 + em, 41 + en, 41 + eo, 41 + ep, 41 + eq, 41 + er, 41 + es, 41 + et, 41 + eu, 41 + ev, 41 + ew, 41 + ex, 41 + ey, 41 + ez, 41 + fa, 41 + fb, 41 + fc, 41 + fd, 41 + fe, 41 + ff, 41 + fg, 41 + fh, 41 + fi, 41 + fj, 41 + fk, 41 + fl, 41 + fm, 41 + fn, 41 + fo, 41 + fp, 41 + fq, 41 + fr, 41 + fs, 41 + ft, 41 + fu, 41 + fv, 41 + fw, 41 + fx, 41 + fy, 41 + fz, 41 + ga, 41 + gb, 41 + gc, 41 + gd, 41 + ge, 41 + gf, 41 + gg, 41 + gh, 41 + gi, 41 + gj, 41 + gk, 41 + gl, 41 + gm, 41 + gn, 41 + go, 41 + gp, 41 + gq, 41 + gr, 41 + gs, 41 + gt, 41 + gu, 41 + gv, 41 + gw, 41 + gx, 41 + gy, 41 + gz, 41 + ha, 41 + hb, 41 + hc, 41 + hd, 41 + he, 41 + hf, 41 + hg, 41 + hh, 41 + hi, 41 + hj, 41 + hk, 41 + hl, 41 + hm, 41 + hn, 41 + ho, 41 + hp, 41 + hq, 41 + hr, 41 + hs, 41 + ht, 41 + hu, 41 + hv, 41 + hw, 41 + hx, 41 + hy, 41 + hz, 41 + ia, 41 + ib, 41 + ic, 41 + id, 41 + ie, 41 + if, 41 + ig, 41 + ih, 41 + ii, 41 + ij, 41 + ik, 41 + il, 41 + im, 41 + in, 41 + io, 41 + ip, 41 + iq, 41 + ir, 41 + is, 41 + it, 41 + iu, 41 + iv, 41 + iw, 41 + ix, 41 + iy, 41 + iz, 41 + ja, 41 + jb, 41 + jc, 41 + jd, 41 + je, 41 + jf, 41 + jg, 41 + jh, 41 + ji, 41 + jj, 41 + jk, 41 + jl, 41 + jm, 41 + jn, 41 + jo, 41 + jp, 41 + jq, 41 + jr, 41 + js, 41 + jt, 41 + ju, 41 + jv, 41 + jw, 41 + jx, 41 + ji, 41 + jz, 41 + ka, 41 + kb, 41 + kc, 41 + kd, 41 + ke, 41 + kf, 41 + kg, 41 + kh, 41 + ki, 41 + kj, 41 + kk, 41 + kl, 41 + km, 41 + kn, 41 + ko, 41 + kp, 41 + kq, 41 + kr, 41 + ks, 41 + kt, 41 + ku, 41 + kv, 41 + kw, 41 + kx, 41 + ky, 41 + kz, 41 + la, 41 + lb, 41 + lc, 41 + ld, 41 + le, 41 + lf, 41 + lg, 41 + lh, 41 + li, 41 + lj, 41 + lk, 41 + 11, 41 + lm, 41 + ln, 41 + lo, 41 + lp, 41 + lq, 41 + lr, 41 + ls, 41 + lt, 41 + lu, 41 + lv, 41 + lw, 41 + lx, 41 + ly, 42 + a, 42 + b, 42 + c, 42 + d, 42 + e, 42 + f, 42 + g, 42 + h, 42 + i, 42 + j, 42 + k, 42 + l, 42 + m, 42 + n, 42 + o, 42 + p, 42 + q, 42 + r, 42 + s, 42 + t, 42 + u, 42 + v, 42 + w, 42 + x, 42 + y, 42 + z, 42 + aa, 42 + ab, 42 + ac, 42 + ad, 42 + ae, 42 + af, 42 + ag, 42 + ah, 42 + ai, 42 + aj, 42 + ak, 42 + al, 42 + am, 42 + an, 42 + ao, 42 + ap, 42 + aq, 42 + ar, 42 + as, 42 + at, 42 + au, 42 + av, 42 + aw, 42 + ax, 42 + ay, 42 + az, 42 + ba, 42 + bb, 42 + bc, 42 + bd, 42 + be, 42 + bf, 42 + bg, 42 + bh, 42 + bi, 42 + bj, 42 + bk, 42 + bl, 42 + bm, 42 + bn, 42 + bo, 42 + bp, 42 + bq, 42 + br, 42 + bs, 42 + bt, 42 + bu, 42 + bv, 42 + bw, 42 + bx, 42 + by, 42 + bz, 42 + ca, 42 + cb, 42 + cc, 42 + cd, 42 + ce, 42 + cf, 42 + cg, 42 + ch, 42 + ci, 42 + cj, 42 + ck, 42 + cl, 42 + cm, 42 + cn, 42 + co, 42 + cp, 42 + cq, 42 + cr, 42 + cs, 42 + ct, 42 + cu, 42 + cv, 42 + cw, 42 + cx, 42 + cy, 42 + cz, 42 + da, 42 + db, 42 + dc, 42 + dd, 42 + de, 42 + df, 42 + dg, 42 + dh, 42 + di, 42 + dj, 42 + dk, 42 + dl, 42 + dm, 42 + dn, 42 + do, 42 + dp, 42 + dq, 42 + dr, 42 + ds, 42 + dt, 42 + du, 42 + dv, 42 + dw, 42 + dx, 42 + dy, 42 + dz, 42 + ea, 42 + eb, 42 + ec, 42 + ed, 42 + ee, 42 + ef, 42 + eg, 42 + eh, 42 + ei, 42 + ej, 42 + ek, 42 + el, 42 + em, 42 + en, 42 + eo, 42 + ep, 42 + eq, 42 + er, 42 + es, 42 + et, 42 + eu, 42 + ev, 42 + ew, 42 + ex, 42 + ey, 42 + ez, 42 + fa, 42 + fb, 42 + fc, 42 + fd, 42 + fe, 42 + ff, 42 + fg, 42 + fh, 42 + fi, 42 + fj, 42 + fk, 42 + fl, 42 + fm, 42 + fn, 42 + fo, 42 + fp, 42 + fq, 42 + fr, 42 + fs, 42 + ft, 42 + fu, 42 + fv, 42 + fw, 42 + fx, 42 + fy, 42 + fz, 42 + ga, 42 + gb, 42 + gc, 42 + gd, 42 + ge, 42 + gf, 42 + gg, 42 + gh, 42 + gi, 42 + gj, 42 + gk, 42 + gl, 42 + gm, 42 + gn, 42 + go, 42 + gp, 42 + gq, 42 + gr, 42 + gs, 42 + gt, 42 + gu, 42 + gv, 42 + gw, 42 + gx, 42 + gy, 42 + gz, 42 + ha, 42 + hb, 42 + hc, 42 + hd, 42 + he, 42 + hf, 42 + hg, 42 + hh, 42 + hi, 42 + hj, 42 + hk, 42 + hl, 42 + hm, 42 + hn, 42 + ho, 42 + hp, 42 + hq, 42 + hr, 42 + hs, 42 + ht, 42 + hu, 42 + hv, 42 + hw, 42 + hx, 42 + hy, 42 + hz, 42 + ia, 42 + ib, 42 + ic, 42 + id, 42 + ie, 42 + if, 42 + ig, 42 + ih, 42 + ii, 42 + ij, 42 + ik, 42 + il, 42 + im, 42 + in, 42 + io, 42 + ip, 42 + iq, 42 + ir, 42 + is, 42 + it, 42 + iu, 42 + iv, 42 + iw, 42 + ix, 42 + iy, 42 + iz, 42 + ja, 42 + jb, 42 + jc, 42 + jd, 42 + je, 42 + jf, 42 + jg, 42 + jh, 42 + ji, 42 + jj, 42 + jk, 42 + jl, 42 + jm, 42 + jn, 42 + jo, 42 + jp, 42 + jq, 42 + jr, 42 + js, 42 + jt, 42 + ju, 42 + jv, 42 + jw, 42 + jx, 42 + ji, 42 + js, 42 + ka, 42 + kb, 42 + kc, 42 + kd, 42 + ke, 42 + kf, 42 + kg, 42 + kh, 42 + ki, 42 + kj, 42 + kk, 42 + kl, 42 + km, 42 + kn, 42 + ko, 42 + kp, 42 + kq, 42 + kr, 42 + ks, 42 + kt, 42 + ku, 42 + kv, 42 + kw, 42 + kx, 42 + ky, 42 + kz, 42 + la, 42 + lb, 42 + lc, 42 + ld, 42 + le, 42 + lf, 42 + lg, 42 + lh, 42 + li, 42 + lj, 42 + lk, 42 + 11, 42 + lm, 42 + ln, 42 + lo, 42 + lp, 42 + lq, 42 + lr, 42 + ls, 42 + lt, 42 + lu, 42 + lv, 42 + lw, 42 + lx, 42 + ly, 43 + a, 43 + b, 43 + c, 43 + d, 43 + e, 43 + f, 43 + g, 43 + h, 43 + i, 43 + j, 43 + k, 43 + 1, 43 + m, 43 + n, 43 + o, 43 + p, 43 + q, 43 + r, 43 + s, 43 + t, 43 + u, 43 + v, 43 + w, 43 + x, 43 + y, 43 + z, 43 + aa, 43 + ab, 43 + ac, 43 + ad, 43 + ae, 43 + af, 43 + ag, 43 + ah, 43 + ai, 43 + aj, 43 + ak, 43 + al, 43 + am, 43 + an, 43 + ao, 43 + ap, 43 + aq, 43 + ar, 43 + as, 43 + at, 43 + au, 43 + av, 43 + aw, 43 + ax, 43 + ay, 43 + az, 43 + ba, 43 + bb, 43 + bc, 43 + bd, 43 + be, 43 + bf, 43 + bg, 43 + bh, 43 + bi, 43 + bj, 43 + bk, 43 + bl, 43 + bm, 43 + bn, 43 + bo, 43 + bp, 43 + bq, 43 + br, 43 + bs, 43 + bt, 43 + bu, 43 + bv, 43 + bw, 43 + bx, 43 + by, 43 + bz, 43 + ca, 43 + cb, 43 + cc, 43 + cd, 43 + ce, 43 + cf, 43 + cg, 43 + ch, 43 + ci, 43 + cj, 43 + ck, 43 + cl, 43 + cm, 43 + cn, 43 + co, 43 + cp, 43 + cq, 43 + cr, 43 + cs, 43 + ct, 43 + cu, 43 + cv, 43 + cw, 43 + cx, 43 + cy, 43 + cz, 43 + da, 43 + db, 43 + dc, 43 + dd, 43 + de, 43 + df, 43 + dg, 43 + dh, 43 + di, 43 + dj, 43 + dk, 43 + dl, 43 + dm, 43 + dn, 43 + do, 43 + dp, 43 + dq, 43 + dr, 43 + ds, 43 + dt, 43 + du, 43 + dv, 43 + dw, 43 + dx, 43 + dy, 43 + dz, 43 + ea, 43 + eb, 43 + ec, 43 + ed, 43 + ee, 43 + ef, 43 + eg, 43 + eh, 43 + ei, 43 + ej, 43 + ek, 43 + el, 43 + em, 43 + en, 43 + eo, 43 + ep, 43 + eq, 43 + er, 43 + es, 43 + et, 43 + eu, 43 + ev, 43 + ew, 43 + ex, 43 + ey, 43 + ez, 43 + fa, 43 + fb, 43 + fc, 43 + fd, 43 + fe, 43 + ff, 43 + fg, 43 + fh, 43 + fi, 43 + fj, 43 + fk, 43 + fl, 43 + fm, 43 + fn, 43 + fo, 43 + fp, 43 + fq, 43 + fr, 43 + fs, 43 + ft, 43 + fu, 43 + fv, 43 + fw, 43 + fx, 43 + fy, 43 + fz, 43 + ga, 43 + gb, 43 + gc, 43 + gd, 43 + ge, 43 + gf, 43 + gg, 43 + gh, 43 + gi, 43 + gj, 43 + gk, 43 + gl, 43 + gm, 43 + gn, 43 + go, 43 + gp, 43 + gq, 43 + gr, 43 + gs, 43 + gt, 43 + gu, 43 + gv, 43 + gw, 43 + gx, 43 + gy, 43 + gz, 43 + ha, 43 + hb, 43 + hc, 43 + hd, 43 + he, 43 + hf, 43 + hg, 43 + hh, 43 + hi, 43 + hj, 43 + hk, 43 + hl, 43 + hm, 43 + hn, 43 + ho, 43 + hp, 43 + hq, 43 + hr, 43 + hs, 43 + ht, 43 + hu, 43 + hv, 43 + hw, 43 + hx, 43 + hy, 43 + hz, 43 + ia, 43 + ib, 43 + ic, 43 + id, 43 + ie, 43 + if, 43 + ig, 43 + ih, 43 + ii, 43 + ij, 43 + ik, 43 + il, 43 + im, 43 + in, 43 + io, 43 + ip, 43 + iq, 43 + ir, 43 + is, 43 + it, 43 + iu, 43 + iv, 43 + iw, 43 + ix, 43 + iy, 43 + iz, 43 + ja, 43 + jb, 43 + jc, 43 + jd, 43 + je, 43 + jf, 43 + jg, 43 + jh, 43 + ji, 43 + jj, 43 + jk, 43 + jl, 43 + jm, 43 + jn, 43 + jo, 43 + jp, 43 + jq, 43 + jr, 43 + js, 43 + jt, 43 + ju, 43 + jv, 43 + jw, 43 + jx, 43 + ji, 43 + jz, 43 + ka, 43 + kb, 43 + kc, 43 + kd, 43 + ke, 43 + kf, 43 + kg, 43 + kh, 43 + ki, 43 + kj, 43 + kk, 43 + kl, 43 + km, 43 + kn, 43 + ko, 43 + kp, 43 + kq, 43 + kr, 43 + ks, 43 + kt, 43 + ku, 43 + kv, 43 + kw, 43 + kx, 43 + ky, 43 + kz, 43 + la, 43 + lb, 43 + lc, 43 + ld, 43 + le, 43 + lf, 43 + lg, 43 + lh, 43 + li, 43 + lj, 43 + lk, 43 + 11, 43 + lm, 43 + ln, 43 + lo, 43 + lp, 43 + lq, 43 + lr, 43 + ls, 43 + lt, 43 + lu, 43 + lv, 43 + lw, 43 + lx, 43 + ly.
[0047]
The preferred mixing ratio of the compound represented by the formula (1) and the compound selected from the compound group A in the composition and the method of the present invention is 1 part by weight of the compound represented by the formula (1). The compound selected from the compound group A is usually 0.001 to 1000 parts by weight, preferably 0.01 to 100 parts by weight, more preferably 0.1 to 10 parts by weight.
[0048]
The preferred treatment amount of the active ingredient compound in the composition of the present invention and the method of the present invention depends on the kind of the target pest to be controlled, but the compound represented by the formula (1) is usually 0.1 to 1000 gai / ha. The compound selected from the compound group A is 0.1 to 1000 gai / ha, preferably the former is 1 to 300 gai / ha, and the latter is 1 to 300 gai / ha.
[0049]
The composition of the present invention includes so-called agricultural pests that infect agricultural and horticultural crops and trees, agricultural diseases, so-called livestock pests that infest livestock and poultry, so-called sanitary pests that adversely affect human living environments such as houses, and the like. It can be applied to mites and nematodes that occur and harm in the scene. Specific examples of pests, mites, nematodes, and diseases that can be controlled using the composition of the present invention include the following, but are not limited thereto.
[0050]
The pest, common cutworm (Spodoptera litura), leaf roller (Cnaphalocrocis medinalis), diamondback moth (Plutella xylostella), cabbage armyworm (Mamestra brassicae), cabbage butterfly (Pieris rapae crucivora), Kaburayaga (Agrotis segetum), smaller tea tortrix (Adoxophyes sp.) , Chahamaki (Homona magnanima), tobacco bat worm (Heliothis virensens), European corn borer (Ostrinia nubilalis), fall army worm (Spodoptera frugiperda), corn ear worm (corn worm worm) rpzea), Lepidopteran pests (Nephotettix cincticeps), brown planthoppers (Nilaparvata lugens), peach aphids (Myzus persicae, etc.) Ladybird (Epilachna vigintiocutuncta), Dromedaria buoy (Anomala cuprea), Rice weevil (Lissorhopterus oryzophilus), Southern corn root worm (Northern corn rootworm, Diab worm worm, Diab trob) avirgifera virgifera, Coleoptera pests such as Scotophilus oryzae, house flies (Musca domestica), squid (Culex pipiens pallens), and turtles Thrips pests such as Thrips palmi, Thrips tabaci, Thrips palmi thrips (Frankliniella occidentalis), etc .; Great Whale (Menacanthus stramineus), Ushihajirami (Bovicola bovis) Mallophaga pests such as, Ushijirami (Haematopinus eurysternus), Ushihosojirami (Linognathus vituli) Anoplura pests such as, citrus red mite (Panonychus citri), two-spotted spider mite (Tetranychus urticae), kanzawai (Tetranychus kanzawai) Spider mites such as red mite (Aculops pelekassi) and Acaphylla theavagrans (Polyphagotarsononemus latus) and Cyclamen mite (Steneotus) Dermatophagoid mites (Sonemus pallidus) and other mites, Tyrophagus putrescentiae, Rhozolyphus robini and other mites, Pterocarpus mites (Phosophilus mite) and Rheoptomychus mite (Polypus mite). Dermatophagoides mite, such as sarcoptic mite, Sarcopes scabiei, etc., sweet potato nematode (Meloidogyne javanica), Pterenchus penetranus and potato cyst deb. and nematodes such as R. rostochiensis.
[0051]
On the other hand, examples of the disease include rice blast (Pyricularia oryzae), sesame leaf blight (Cochliobolus miyabeanus), sheath blight (Rhizoctonia solani), and wheat powdery mildew (Erysiphe griffis. Tritici), leaf spot disease (Pyrenophoragraminea), reticulum disease (Pyrenophora teres), red mold (Gibberella zeae), rust (Puccinia striiformis, P. graminis, P. recondita, P. recondite, P. recondita, P. recondide, P. recondite, P. recondide) Tipula sp., Micronectriella nivais, Utiligo tritici, U.S.A. uda), eye spots (Pseudocercosporella herpotrichoids), scald disease (Rhynchosporium secalis), leaf blight (Septria tritici), wilt (Leptosphaeia nodoke scab, Leptosphaeia nodore scab) Fruit rot (Penicillium digitalum, P. italicum), Monilia disease of apples (Selerotinia mali), rot of varieties (Valsa mali), powdery mildew (Podosphaera lucatrica), spotted leaf squirrel (Altera varia) , Na Scab (Venturia nashikola), black scab (Alternaria kikuchiana), red scab (Gymnosporangium haracanum), peach scab (Sclerolinia cinepopsipopsis phospomous phospomphos) Downy mildew (Plasmopara viticola), black rot (Elsinoe ampelina), late rot (Glomerella singulata), powdery mildew (Uncinula necator), rust (Phakopsora apopsop, scab, scab) Deciduous disease (Cercospora ka) j, Mycosphaerella nawae, downy mildew of cucumber (Pseudoperenospora cubensis), anthracnose (Colletotrichumum genarium), powdery mildew (Sphaerothela falginae disease, tomato blight disease) Leaf blight (Alternaria solani), leaf mold (Cladosporium fulvum), eggplant brown spot (Phomopsis vexans), powdery mildew (Erysiphe cichoracoarum), black spot of cruciferous vegetables (Alternaria placia cora errabia japonica) icae), green onion rust (Puccinia allii), soybean purpura (Cercospora kikuchii), black rot (Elsinoe glycines), black spot (Diaporthe santium ulium culm) Disease (Mycosphaerella personatum), brown spot (Cercospora arachidicola), pea powdery mildew (Erysiphe pisi), potato summer blight (Alternaria solani), and strawberry powdery mildew (Echo scotch) reticulatum), scab (Els) noe leucospila, tobacco scab (Alternaria lingipes), powdery mildew (Erysiphe cichoracearum), anthracnose (Colletotrichum tabacum), sugar beet scab (Cercospora betcolar scab) Diseases (Sphaerotheca pannosa), chrysanthemum leaf spot of chrysanthemum (Septoria chrysantheminidicii), white rust (Puccinia horiana), gray mold of various crops (Botrytis cinerea), and various rots of icrotrophy and spores of S. rotio ini rot. Can be
[0052]
When the acrylonitrile compound represented by the formula (1) is combined with the compound shown in Table 2 above, the composition of the present invention and the method of the present invention exhibit an excellent synergistic effect particularly on mites. Among them, red mites, red spider mites, red mite, Kanzawa spider mite, red mite, carnation rust mite, tulip rust mite, citrus rust mite, peach rust mite, apple rust mite, chan rust mite, grape rust mite, pear mite such as red sick mite, sword mite, etc. It exerts a better synergistic effect on dust mites.
[0053]
The acrylonitrile compound of the present invention represented by the formula (1) can be synthesized by the method described in the following scheme 1. That is, by reacting a cyanomethylbenzene derivative represented by the general formula (2) with a carboxylic acid derivative represented by the general formula (3) in the presence of a base, (1) , ) Can be synthesized and further reacted with a compound represented by the general formula (4) to obtain a compound represented by the formula (1).
[Scheme 1]
[0054]
Embedded image
Figure 2004155693
[0055]
[G, A and B in Scheme 1 represent the same meaning as described above, and L 1 And L 2 Is a good leaving group such as chlorine, bromine, iodine, C 1 ~ C 4 Alkylsulfonyloxy, benzenesulfonyloxy, toluenesulfonyloxy, 1-imidazolyl and 1-pyrazolyl. ].
[0056]
In some cases, it is preferable to use a base in the above method. Examples of the base used include alkali metal alkoxides such as sodium ethoxide, sodium methoxide and potassium t-butoxide, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, and alkali metal carbonates such as sodium carbonate and potassium carbonate. And organic bases such as triethylamine, pyridine and DBU, organic lithium compounds such as butyllithium, lithium amides such as lithium diisopropylamide and lithium bistrimethylsilylamide, and sodium hydride.
[0057]
The above reaction can be carried out in a solvent inert to the reaction. Examples of the solvent include lower alcohols such as methanol and ethanol, aromatic hydrocarbons such as benzene and toluene, diethyl ether, tetrahydrofuran, 1,4- Ethers such as dioxane, 1,2-dimethoxyethane and 1,2-diethoxyethane; ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone; halogenated hydrocarbons such as methylene chloride, chloroform and 1,2-dichloroethane Amides such as dimethylformamide, dimethylacetamide and 1,3-dimethylimidazolidinone; nitriles such as acetonitrile; dimethylsulfoxide; and a mixed solvent thereof. In some cases, a mixed solvent of these solvents and water can also be used, and good results may be obtained by adding a quaternary ammonium salt such as tetra-n-butylammonium bromide as a catalyst. The reaction temperature can be set to any temperature from -70 ° C to 200 ° C, and preferably from 0 ° C to 150 ° C or, when a solvent is used, from -70 ° C to the boiling point of the solvent. The base ranges from 0.05 to 10 equivalents, preferably 0.05 to 3 equivalents, of the reaction substrate.
[0058]
The compound represented by the formula (1) can be obtained from the reaction solution by a conventional method. It can be separated and purified by any purification method.
[0059]
When the compound represented by the formula (1) has an asymmetric carbon, the compound represented by the formula (1) may be an optically active compound (+), (-), or both. May be any of the racemates contained in the ratio.
[0060]
In the composition of the present invention, at least one kind of the acritonitrile compound represented by the formula (1) and at least one kind selected from the compound group A can be used as a mixture as it is. Mix with a solid or liquid carrier and, if desired, surfactants, penetrants, spreading agents, thickeners, antifreeze agents, binders, anti-caking agents, disintegrants, defoamers, preservatives and degradation Inhibitors and the like are added, and a liquid concentrate (soluble concentrate), an emulsion (emulsifiable concentrate), a wettable powder (wettable powder), a water solvent (water soluble powder), a water dispersible powder (water dispersible granule), a water dispersible granule (water dispersible granule), water soluble granule, suspension (susp) nsion concentrate, concentrated emulsification, suspoemulsion, microemulsion, dustable powder, granule, and gel (gel). And can be put to practical use. In addition, from the viewpoint of labor saving and improvement of safety, the above-mentioned preparation of any dosage form can be provided by being enclosed in a water-soluble package such as a water-soluble capsule and a bag of a water-soluble film.
[0061]
Examples of the solid carrier include natural minerals such as quartz, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite and diatomaceous earth, and inorganic salts such as calcium carbonate, ammonium sulfate, sodium sulfate and potassium chloride. Salts, synthetic silica and synthetic silicates.
[0062]
Examples of the liquid carrier include alcohols such as ethylene glycol, propylene glycol and isopropanol, aromatic hydrocarbons such as xylene, alkylbenzene and alkylnaphthalene, ethers such as butyl cellosolve, ketones such as cyclohexanone, and esters such as γ-butyrolactone. And acid amides such as N-methylpyrrolidone and N-octylpyrrolidone, vegetable oils such as soybean oil, rapeseed oil, cottonseed oil and castor oil, and water.
[0063]
These solid and liquid carriers may be used alone or in combination of two or more.
[0064]
Examples of the surfactant include polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene styryl phenyl ether, polyoxyethylene polyoxypropylene block copolymer, polyoxyethylene fatty acid ester, sorbitan fatty acid ester and polyoxyethylene sorbitan. Nonionic surfactants such as fatty acid esters, alkyl sulfates, alkyl benzene sulfonates, lignin sulfonates, alkyl sulfosuccinates, naphthalene sulfonates, alkyl naphthalene sulfonates, salts of formalin condensates of naphthalene sulfonic acids, Salts of formalin condensates of alkylnaphthalenesulfonic acids, polyoxyethylene alkylaryl ether sulfates and phosphates, polyoxyethylenes Anionic surfactants such as lylphenyl ether sulfate and phosphate, polycarboxylates and polystyrene sulfonates, cationic surfactants such as alkylamine salts and alkylquaternary ammonium salts, and amphoteric types such as amino acid type and betaine type Surfactants.
[0065]
The content of these surfactants is not particularly limited, but is preferably in the range of usually 0.05 to 20 parts by weight based on 100 parts by weight of the preparation of the present invention. These surfactants may be used alone or in combination of two or more.
[0066]
Next, a formulation example of the preparation when the composition of the present invention is used will be described. However, the composition examples of the present invention are not limited only to these. In the following formulation examples, "parts" means parts by weight.
[0067]
[Wettable powder]
Active ingredient compound 0.1-80 parts
Solid carrier 5-98.9 parts
Surfactant 1-10 parts
Others 0-5 copies
Other examples include an anti-caking agent and an anti-decomposition agent.
[0068]
[Emulsifiable concentrate]
Active ingredient compound 0.1-30 parts
Liquid carrier 45 to 95 parts
Surfactant 4.9-15 parts
Others 0-10 copies
Other examples include a spreading agent, a decomposition inhibitor and the like.
[0069]
[Suspension concentrate]
Active ingredient compound 0.1-70 parts
Liquid carrier 15-98.89 parts
Surfactant 1 to 12 parts
Others 0.01 to 30 parts
Other examples include an antifreezing agent and a thickener.
[0070]
[Water dispersible granule]
Active ingredient compound 0.1 to 90 parts
Solid carrier 0-98.9 parts
Surfactant 1-20 parts
Others 0-10 copies
Other examples include a binder and a decomposition inhibitor.
[0071]
[Soluble concentrate]
Active ingredient compound 0.01 to 70 parts
Liquid carrier 20-99.99 parts
Others 0-10 copies
Other examples include an antifreezing agent and a spreading agent.
[0072]
[Granule]
Active ingredient compound 0.01 to 80 parts
Solid carrier 10 to 99.99 parts
Others 0-10 copies
Other examples include a binder and a decomposition inhibitor.
[0073]
[Dustable powder]
Active ingredient compound 0.01-30 parts
Solid carrier 65-99.99 parts
Other 0-5 copies
Other examples include a drift inhibitor, a decomposition inhibitor, and the like.
[0074]
(Formulation example)
Next, specific examples of agrochemical formulations containing the composition of the present invention as an active ingredient will be shown, but the invention is not limited thereto. In the following formulation examples, "parts" means parts by weight.
[0075]
[Formulation Example 1] wettable powder
Compound No. 1 10 copies
Compound No. a 10 copies
Pyrophilite 76 parts
Solpol 5039 2 parts
(Mixture of nonionic and anionic surfactants: trade name of Toho Chemical Industry Co., Ltd.)
Carplex # 80D 2 copies
(Synthetic hydrous silicic acid: Shionogi & Co., Ltd. brand name)
The above is uniformly mixed and pulverized to obtain a wettable powder.
[0076]
[Formulation Example 2] milk preparation (emulsifiable concentrate)
Compound No. 2 3 copies
Compound No. b 2 parts
Xylene 75 parts
N-methylpyrrolidone 15 parts
Solpol 2680 5 parts
(Mixture of nonionic and anionic surfactants: trade name of Toho Chemical Industry Co., Ltd.)
The above are uniformly mixed to form an emulsion.
[0077]
[Formulation Example 3] Suspension concentrate
Compound No. 3 15 copies
Compound No. c 10 parts
Agrisol S-710 10 parts
(Nonionic surfactant: Kao Corporation trade name)
Lunox 1000C 0.5 parts
(Anionic surfactant: trade name of Toho Chemical Industry Co., Ltd.)
Xanthan gum 0.2 parts
64.3 parts of water
After mixing the above uniformly, wet pulverization is performed to obtain a suspension.
[0078]
[Formulation Example 4] water dispersible granule
Compound No. 4 40 copies
Compound No. d 35 parts
Hytenol NE-15 5 parts
(Anionic surfactant: Daiichi Kogyo Seiyaku Co., Ltd.)
Vanilex N 10 parts
(Anionic surfactant: Nippon Paper Industries Co., Ltd.)
Carplex # 80D 10 copies
(Synthetic hydrous silicic acid: Shionogi & Co., Ltd. brand name)
After uniformly mixing and pulverizing the above, a small amount of water is added, and the mixture is stirred and mixed, granulated by an extrusion granulator, and dried to obtain a wettable powder.
[0079]
[Formulation Example 5] granule
Compound No. 5 3 copies
Compound No. e 2 parts
Bentonite 50 parts
Talc 45 parts
After uniformly mixing and pulverizing the above, a small amount of water is added, and the mixture is stirred and mixed. The mixture is granulated by an extruder and dried to obtain granules.
[0080]
[Compounding Example 6] Powder (dustable powder)
Compound No. 6 2 copies
Compound No. f 1 copy
Carplex # 80D 0.5 parts
(White carbon: Shionogi & Co., Ltd. brand name)
Kaolinite 95 parts
1.5 parts of diisopropyl phosphate
The above is uniformly mixed and pulverized to obtain a powder.
[0081]
In use, the above-mentioned wettable powder, emulsion, flowable and granular wettable powder are diluted 50 to 20,000 times with water and dispersed so that the active ingredient becomes 0.005 to 50 kg per hectare (ha).
[0082]
【Example】
Hereinafter, a synthesis example of the acrylonitrile compound represented by the formula (1) of the present invention will be specifically described.
[0083]
Synthesis Example 1 Synthesis of 2- (4-chlorophenyl) -3- (1,3,4-trimethylpyrazol-5-yl) -3-hydroxy-acrylonitrile (Compound No. 1)
5.0 g of 4-chlorophenylacetonitrile and 5.69 g of 1,3,4-trimethyl-5-carbonyl chloride were dissolved in 60 ml of tetrahydrofuran, and 8.13 g of potassium tert-butoxide was added under ice cooling. After stirring at room temperature for 4 hours, the solvent was distilled off under reduced pressure, the residue was acidified by adding diluted hydrochloric acid, extracted with ethyl acetate, washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The precipitate was washed with diisopropyl ether to obtain 7.43 g of the title compound. Melting point: 219-220C.
[0084]
Synthesis Example 2 Synthesis of 2- (4-chlorophenyl) -3-pivaloyloxy-3- (1,3,4-trimethylpyrazol-5-yl) acrylonitrile (Compound No. 2)
1.5 g of 2- (4-chlorophenyl) -3- (1,3,4-trimethylpyrazol-5-yl) -3-hydroxy-acrylonitrile was dissolved in 20 ml of tetrahydrofuran, and 0.64 g of potassium tert-butoxide was added. Thereafter, 0.75 g of pivaloyl chloride was added dropwise, and the mixture was stirred overnight at room temperature. The reaction mixture was poured into water, extracted with ethyl acetate, washed with water, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained oil was crystallized from diisopropyl ether to give 1.37 g of the title compound. Got. Melting point: 148 [deg.] C.
[0085]
An acrylonitrile compound represented by the formula (1) shown in Table 1 was synthesized according to the above synthesis example. Table 4 shows the physical properties of the synthesized compounds.
[0086]
[Table 4]
Figure 2004155693
Figure 2004155693
[0087]
Next, in order to clarify the usefulness of the present invention, an efficacy test example is specifically shown below.
[0088]
[Test Example 1] Efficacy test against citrus mite
The compounds listed in Table 4 above and the compounds listed in Table 3 above were each formulated into a 10% emulsion (25% wettable powder depending on the compound), and the formulation was mixed with a spreading agent. The solution was diluted with water to prepare a drug solution having a predetermined concentration. Next, from the fruit of the mandarin orange mites parasitized, the skin of the parasitized part was cut out to make small pieces (about 5 mm x 5 mm), which were fixed in a petri dish using a 0.3% agar solution containing crystal violet. Under a stereoscopic microscope, all rust mite larvae and, if necessary, some adults were removed from the slices, and the number of rust mite adults per slice was adjusted to 20 to 30. Each of the thus prepared test sections was sprayed with 5 ml of a drug solution of a predetermined concentration, air-dried, covered with a perforated lid, and stored in a constant temperature chamber at 25 ° C. The number of dead insects after 4 days was investigated, and the mortality was calculated from the following formula. The test was performed in two sections.
[0089]
Mortality (%) = Number of dead insects / Number of test insects x 100
From the mortality rate for each chemical concentration, the half-lethal concentration (LC 50 Value). Further, using the formula of the Sun & Johnson method (Journal of Economic Entomology, 1960, vol. 55, p. 887), which is usually used to determine the degree of synergistic effect (synergistic effect), The coefficients were calculated. The synergistic coefficient is expressed by the following equation.
[0090]
Synergy coefficient = actual toxicity index of admixture / theoretical toxicity index of admixture x 100
However,
Actual toxicity index of admixture: LC of [A] 50 / [A] [B] LC of mixed agent 50 × 100
Theoretical toxicity index of the mixture: ([A] toxicity index x [A] [B]% of [A] in mixture + toxicity index of [B] x [A] [B] in mixture] [% Of [B]) / 100
[A]: Acrylonitrile compound represented by formula (1)
[B]: a compound selected from compound group A
%: Weight percentage based on the total weight of [A] and [B]
Toxicity index of [A]: 100
Toxicity index of [B]: (LC of [A] 50 / LC of [B] 50 ) × 100
It is.
[0091]
When the value of the synergistic coefficient is larger than 100, the synergistic effect is higher, when the value is equal to 100, the additive effect is obtained, and when the value is smaller than 100, the antagonistic effect is higher.
[0092]
As a result of the test, the synergistic coefficient was larger than 100 in the following compound combinations.
[0093]
Combinations of compounds with synergistic coefficients larger than 100: 1 + v, 1 + df, 1 + dg, 1 + gh, 1 + gk, 1 + gl, 1 + gp, 1 + gr, 1 + gt, 1 + gy, 1 + gz, 1 + ha, 1 + hd, 1 + ht, 1 + hu, 1 + il, 1 + hu, 1 + il 1 + ji, 1 + kl, 1 + kp, 1 + ly, 2 + v, 2 + df, 2 + dg, 2 + gh, 2 + gk, 2 + gl, 2 + gp, 2 + gr, 2 + gt, 2 + gy, 2 + gz, 2 + ha, 2 + h, +2,2,2,2,2,2,2,2,2,2,2 2 + ly, 3 + v, 3 + df, 3 + dg, 3 + gh, 3 + gk, 3 + gl, 3 + gp, 3 + gr, 3 + gt, 3 + gy, 3 + gz, 3 + ha, 3 + hd, 3 + hg, 3 + ht, 3 + hu, 3 + il, 3 + iq, 3 zy, 3 + kl, 3 + kp, 3 + ly, 4 + v, 4 + df, 4 + dg, 4 + gh, 4 + gk, 4 + gl, 4 + gp, 4 + gr, 4 + gt, 4 + gy, 4 + gz, 4 + ha, 4 + hd, ++ 4,4,4,4,4,4,4,4,4 4 + ly, 5 + v, 5 + df, 5 + dg, 5 + gh, 5 + gk, 5 + gl, 5 + gp, 5 + gr, 5 + gt, 5 + gy, 5 + gz, 5 + ha, 5 + hd, 5 + hg, 5 + ht, 5 + hu, 5 + il, 5 + 6,5 + 6,5 + 6,5 + 6,5 + 6,5 + 6 6 + dg, 6 + gh, 6 + gk, 6 + gl, 6 + gp, 6 + gr, 6 + gt, 6 + gy, 6 + gz, 6 + ha, 6 + hd, 6 + hg, 6 + ht, 6 + hu, 6 + il, 6 + iq, 6 + ji, 6+ 1, 6 + kp, 6 + ly, 7 + v, 7 + df, 7 + dg, 7 + gh, 7 + gk, 7 + gl, 7 + gp, 7 + gr, 7 + gt, 7 + gy, 7 + gz, 7 + ha, 7 + hd, 7 + ht, 7 + 7,7 + 7,7 + 7,7 + 7 8 + v, 8 + df, 8 + dg, 8 + gh, 8 + gk, 8 + gl, 8 + gp, 8 + gr, 8 + gt, 8 + gy, 8 + gz, 8 + ha, 8 + hd, 8 + hg, 8 + ht, 8 + hu, 8 + il, 8 + iq, 8 + 9,8 + 9,8 + 9,8 + 9 9 + gh, 9 + gk, 9 + gl, 9 + gp, 9 + gr, 9 + gt, 9 + gy, 9 + gz, 9 + ha, 9 + hd, 9 + hg, 9 + ht, 9 + hu, 9 + il, 9 + iq, 9 + jy, 9 + kl, 9 + kp , 9 + ly, 10 + v, 10 + df, 10 + dg, 10 + gh, 10 + gk, 10 + gl, 10 + gp, 10 + gr, 10 + gt, 10 + gy, 10 + gz, 10 + ha, 10 + hd, 10 + hg, 10 + ht, 10 + hu, 10 + il, 10 + l, + 10,10 + l, + 10,10 + 11 , 11 + dg, 11 + gh, 11 + gk, 11 + gl, 11 + gp, 11 + gr, 11 + gt, 11 + gy, 11 + gz, 11 + ha, 11 + hd, 11 + hg, 11 + ht, 11 + hu, 11 + il, 11 + iq, 11 + zy, 11 + k, 12 + g, + 12,11 + g, + 12 , 12 + gl, 12 + gp, 12 + gr, 12 + gt, 12 + gy, 12 + gz, 2 + ha, 12 + hd, 12 + hg, 12 + ht, 12 + hu, 12 + il, 12 + iq, 12 + yy, 12 + kl, 12 + kp, 12 + ly, 13 + v, 13 + df, 13 + dg, 13 + gh, 13 + gk, 13 + gl, 13 + g, 13 + g, 13 + g, 13 + g, 13 + g, 13 + g, 13 + g 13 + ht, 13 + hu, 13 + il, 13 + iq, 13 + yy, 13 + kl, 13 + kp, 13 + ly, 14 + v, 14 + df, 14 + dg, 14 + gh, 14 + gk, 14 + gl, 14 + gp, 14 + gr, 14 + gt, 14 + gt, + h, + 14h, + 14h, + 14h 14 + iq, 14 + ji, 14 + kl, 14 + kp, 14 + ly, 15 + v, 5 + df, 15 + dg, 15 + gh, 15 + gk, 15 + gl, 15 + gp, 15 + gr, 15 + gt, 15 + gy, 15 + gz, 15 + ha, 15 + hd, 15 + hg, 15 + ht, 15 + hu, 15 + il, 15 + iq, + 16,16 + g, + 16, + 16, + 16 16 + gk, 16 + gl, 16 + gp, 16 + gr, 16 + gt, 16 + gy, 16 + gz, 16 + ha, 16 + hd, 16 + hg, 16 + ht, 16 + hu, 16 + il, 16 + iq, 16 + ji, 16 + kl, 16 + kp, 16 + ly, +17, +17, g + 17, +17, g + 17 17 + gr, 17 + gt, 17 + gy, 17 + gz, 17 + ha, 17 + hd, 17 + hg, 17 + ht, 17 + hu, 17 + il, 17 + iq, 17 + zy, 17 + kl, 17 + kp, 17 + ly, 18 + v, 18 + df, 18 + dg, 18 + gh, 18 + gk, 18 + gl, 18 + gp, 18 + gt, 18 + gt, 18 + gh, 18 + gh, 18 + gt, 18 + gt 18 + il, 18 + iq, 18 + zy, 18 + kl, 18 + kp, 18 + ly, 19 + v, 19 + df, 19 + dg, 19 + gh, 19 + gk, 19 + gl, 19 + gp, 19 + gr, 19 + gt, 19 + gy, 19 + gh, 19 + gh, 19 + h, 19 + h, 19 + h, 19 + h, 19 + h 19 + kl, 19 + kp, 19 + ly, 20 + v, 20 + df, 20 + dg, 0 + gh, 20 + gk, 20 + gl, 20 + gp, 20 + gr, 20 + gt, 20 + gy, 20 + gz, 20 + ha, 20 + hd, 20 + hg, 20 + ht, 20 + hu, 20 + il, 20 + iq, 20 + jy, 20 + kl, +21, 21 + g, +21, +21, +21 21 + gp, 21 + gr, 21 + gt, 21 + gy, 21 + gz, 21 + ha, 21 + hd, 21 + hg, 21 + ht, 21 + hu, 21 + il, 21 + iq, 21 + zy, 21 + kl, 21 + kp, 21 + ly, 22 + v, 22 + df, 22 + d, + 22,22 + g, + 22,22 + d 22 + gy, 22 + gz, 22 + ha, 22 + hd, 22 + hg, 22 + ht 22 + hu, 22 + il, 22 + iq, 22 + yy, 22 + kl, 22 + kp, 22 + ly, 23 + v, 23 + df, 23 + dg, 23 + gh, 23 + gk, 23 + gl, 23 + gp, 23 + gr, 23 + gt, 23 + gy, 23 + gh, +23, 23 + h, +23, 23 + h, +23 23 + zy, 23 + kl, 23 + kp, 23 + ly, 24 + v, 24 + df, 24 + dg, 24 + gh, 24 + gk, 24 + gl, 24 + gp, 24 + gr, 24 + gt, 24 + gy, 24 + gz, 24 + ha, 24 + hd, 24 + h, + h, + h, +24, 24 + gh, + 24h 24 + ly, 25 + v, 25 + df, 25 + dg, 25 + gh, 25 + gk, 25 + gl, 25 + gp, 25 + gr, 25 + gt, 25 + gy, 25 + gz, 25 + ha, 25 + hd, 25 + hg, 25 + ht, 25 + hu, 25 + il, 25 + iq, 25 + jay, 25 + kl, 25 + kp, 25 + ly, 26 + v, 26 + g, +26, 26 + g, +26, 26 + df 26 + gt, 26 + gy, 26 + gz, 26 + ha, 26 + hd, 26 + hg, 26 + ht, 26 + hu, 26 + il, 26 + iq, 26 + ji, 26 + kl, 26 + kp, 26 + ly, 27 + v, 27 + df, 27 + dg, 27 + g, +27, g + 27, g + 27, g + 27, g + 27 27 + ha, 27 + hd, 27 + hg, 27 + ht, 27 + hu, 27 + il 27 + iq, 27 + zy, 27 + kl, 27 + kp, 27 + ly, 28 + v, 28 + df, 28 + dg, 28 + gh, 28 + gk, 28 + gl, 28 + gp, 28 + gr, 28 + gt, 28 + gy, 28 + gz, 28 + ha, 28 + hd, 28 + h, 28 + h, 28 + gh, 28 + gh, 28 + gh 28 + kp, 28 + ly, 29 + v, 29 + df, 29 + dg, 29 + gh, 29 + gk, 29 + gl, 29 + gp, 29 + gr, 29 + gt, 29 + gy, 29 + gz, 29 + ha, 29 + hd, 29 + hg, 29 + ht, 29 + hu, 29 + il, +29, 29 + 29 30 + df, 30 + dg, 30 + gh, 30 + gk, 30 + gl, 30 + gp 30 + gr, 30 + gt, 30 + gy, 30 + gz, 30 + ha, 30 + hd, 30 + hg, 30 + ht, 30 + hu, 30 + il, 30 + iq, 30 + gy, 30 + kl, 30 + kp, 30 + ly, 31 + v, 31 + df, 31 + g, +31,31,31,31,31,31,31,31,31. 31 + gz, 31 + ha, 31 + hd, 31 + hg, 31 + ht, 31 + hu, 31 + il, 31 + iq, 31 + yy, 31 + kl, 31 + kp, 31 + ly, 32 + v, 32 + df, 32 + dg, 32 + gh, 32 + gk, 32 + g, +32, 32 + 32, 32 + 32, 32 + 32 32 + hg, 32 + ht, 32 + hu, 32 + il, 32 + iq, 32 + ji , 32 + kl, 32 + kp, 32 + ly, 33 + v, 33 + df, 33 + dg, 33 + gh, 33 + gk, 33 + gl, 33 + gp, 33 + gr, 33 + gt, 33 + gy, 33 + gz, 33 + ha, 33 + hd, 33 + hg, +33, 33 + gh, +33, 33 + gh, +33, 33 + gh , 34 + v, 34 + df, 34 + dg, 34 + gh, 34 + gk, 34 + gl, 34 + gp, 34 + gr, 34 + gt, 34 + gy, 34 + gz, 34 + ha, 34 + hd, 34 + hg, 34 + ht, 34 + hu, 34 + il, 34 + iq, 34 + j, 34 + j, 34 + j, 34 + j, 34 + j , 35 + gh, 35 + gk, 35 + gl, 35 + gp, 35 + gr, 35 + gt 35 + gy, 35 + gz, 35 + ha, 35 + hd, 35 + hg, 35 + ht, 35 + hu, 35 + il, 35 + iq, 35 + jay, 35 + kl, 35 + kp, 35 + ly, 36 + v, 36 + df, 36 + dg, 36 + g, 36 + g, + g, 36 + g, 36 + g, 36 + g, 36 + g 36 + hd, 36 + hg, 36 + ht, 36 + hu, 36 + il, 36 + iq, 36 + ji, 36 + kl, 36 + kp, 36 + ly, 37 + v, 37 + df, 37 + dg, 37 + gh, 37 + gk, 37 + gl, 37 + gp, 37 + gt, +37, 37 + gt, +37, 37 + gt, +37 37 + hu, 37 + il, 37 + iq, 37 + zy, 37 + kl, 37 + k , 37 + ly, 38 + v, 38 + df, 38 + dg, 38 + gh, 38 + gk, 38 + gl, 38 + gp, 38 + gr, 38 + gt, 38 + gy, 38 + gz, 38 + ha, 38 + hd, 38 + hg, 38 + ht, 38 + hu, 38 + il, 38 + y, 38,38,38,38,38 , 39 + dg, 39 + gh, 39 + gk, 39 + gl, 39 + gp, 39 + gr, 39 + gt, 39 + gy, 39 + gz, 39 + ha, 39 + hd, 39 + hg, 39 + ht, 39 + hu, 39 + il, 39 + iq, 39 + yy, 39 + k, + 40,40 + g, + 40,40 + g , 40 + gl, 40 + gp, 40 + gr, 40 + gt, 40 + gy, 40 + gz , 40 + ha, 40 + hd, 40 + hg, 40 + ht, 40 + hu, 40 + il, 40 + iq, 40 + jay, 40 + kl, 40 + kp, 40 + ly, 41 + v, 41 + df, 41 + dg, 41 + gh, 41 + gk, 41 + gl, 41 + g, + 41,41,41,41,41,41 , 41 + ht, 41 + hu, 41 + il, 41 + iq, 41 + zy, 41 + kl, 41 + kp, 41 + ly, 42 + v, 42 + df, 42 + dg, 42 + gh, 42 + gk, 42 + gl, 42 + gp, 42 + gr, 42 + gt, 42 + gt, + 42h, + 42h, + 42h , 42 + iq, 42 + ji, 42 + kl, 42 + kp, 42 + ly, 43 + v 43 + df, 43 + dg, 43 + gh, 43 + gk, 43 + gl, 43 + gp, 43 + gr, 43 + gt, 43 + gy, 43 + gz, 43 + ha, 43 + hd, 43 + hg, 43 + ht, 43 + hu, 43 + il, 43 + iq, 43 + jy, 43 + kl, 43 + kp, 43 + ly.
[0094]
【The invention's effect】
The composition of the present invention and the method of the present invention exhibit excellent synergistic control effects against various pests.

Claims (6)

以下の式(1)で表されるアクリロニトリル化合物の1種以上と、以下の化合物群Aより選ばれる化合物の1種以上を含有する殺虫、殺ダニ、殺線虫、殺菌又は殺バクテリア組成物。
式(1):
Figure 2004155693
[式中、 Aは、
Figure 2004155693
Figure 2004155693
Figure 2004155693
Figure 2004155693
Figure 2004155693
であり、
Bは、H、CR、CHR、C〜Cハロアルキル、テトラヒドロピラニル、Si(CH、SORe、SONHRb、SONRaRb、C(S)NHRb、C(S)NRaRb、C(O)Rf、P(O)RgRh、P(S)RgRh、アルカリ金属、アルカリ土類金属またはNHRiRjRkであり、
Gは、H、ハロゲン、C〜Cアルキル、Rcで置換されたC〜Cアルキル、C〜Cハロアルキル、C〜Cアルキルで置換されていてもよいC〜Cシクロアルキル、C〜Cアルコキシ、C〜Cアルケニルオキシ、C〜Cアルキニルオキシ、C〜Cハロアルコキシ、C〜Cアルキルスルフェニル、C〜Cアルキルスルフィニル、C〜Cアルキルスルホニル、C〜Cアルケニルスルフェニル、C〜Cアルケニルスルフィニル、C〜Cアルケニルスルホニル、C〜Cアルキニルスルフェニル、C〜Cアルキニルスルフィニル、C〜Cアルキニルスルホニル、C〜Cハロアルキルスルフェニル、C〜Cハロアルキルスルフィニル、C〜Cハロアルキルスルホニル、C〜Cハロアルケニルスルフェニル、C〜Cハロアルケニルスルフィニル、C〜Cハロアルケニルスルホニル、NO、CN、−NU、ナフチル、Rcで置換されたメトキシ、C〜Cアルコキシカルボニル、C〜Cアルコキシアルキル、C〜Cアルキルカルボニル、C〜Cハロアルキルカルボニル、C〜Cアルキルカルボニルオキシ、C〜Cハロアルキルカルボニルオキシ、C〜Cジアルキルアミノカルボニルオキシ、Zで置換されていてもよいフェニル、Zで置換されていてもよいフェノキシ、Zで置換されていてもよいベンゾイル、Zで置換されていてもよいピリジル、Zで置換されていてもよいピリジルオキシ、Zで置換されていてもよいチエニル、隣接した置換位置で結合したメチレンジオキシ、隣接した置換位置で結合したハロメチレンジオキシ及び−N=CTの中から選ばれる1ないし4個の置換基、または隣接した置換位置で結合したアルキレン基によって形成される5ないし8員環であり、
Y、Y及びYは、各々独立にH、ハロゲン、C〜Cアルキル、C〜Cハロアルキル、C〜Cアルコキシ、C〜Cハロアルコキシ、C〜Cアルキルスルフェニル、C〜Cアルキルスルフィニル、C〜Cアルキルスルホニル、C〜Cハロアルキルスルフェニル、C〜Cハロアルキルスルフィニル、C〜Cハロアルキルスルホニル、NOまたはCNであるか、または隣接した置換位置で結合したアルキレン基によって形成される5員環、6員環、7員環もしくは8員環であり、
は、H、C〜CアルキルまたはC〜Cハロアルキルであり、
Zは、各々独立して、ハロゲン、C〜Cアルキル、C〜Cハロアルキル、C〜Cアルコキシ、C〜Cハロアルコキシ、C〜Cアルキルスルフェニル、C〜Cアルキルスルフィニル、C〜Cアルキルスルホニル、C〜Cアルケニルスルフェニル、C〜Cアルケニルスルフィニル、C〜Cアルケニルスルホニル、C〜Cハロアルキルスルフェニル、C〜Cハロアルキルスルフィニル、C〜Cハロアルキルスルホニル、NO、CN、−NU及びC〜Cアルコキシカルボニルの中から選ばれる1ないし5個の置換基であり、
、R、R及びRaは、各々独立にC〜Cアルキルであり、
Rbは、H、C〜Cアルキル、またはTで置換されていてもよいフェニルであり、
Rcは、ハロゲン、C〜Cアルキル、C〜Cアルコキシ及びC〜Cハロアルキルの中から任意に選ばれる1種以上で置換されていてもよいフェニルであり、
Rdは、ハロゲン、C〜Cアルキル及びC〜Cハロアルキルの中から任意に選ばれる1種以上で置換されていてもよいベンゾイルであり、
Reは、C〜Cアルキル、C〜Cハロアルキル、またはTで置換されてい
てもよいフェニルであり、
Rfは、C〜C20アルキル、C〜Cアルケニル、C〜Cハロアルキル、C〜Cアルコキシアルキル、C〜Cハロシクロアルキル、Rcで置換されたC〜Cアルキル、C〜Cアルキルで置換されていてもよいC〜Cシクロアルキル、Rcで置換されたシクロアルキル、Rc及びC〜Cアルキルで置換されたシクロプロピル、Rc及びハロゲンで置換されたC〜Cシクロアルキル基、T及びC〜Cアルキルで置換されたシクロプロピル基、Rcで置換されたC〜Cアルケニル、C〜Cアルコキシ、C〜Cハロアルコキシ、C〜Cアルケニルオキシ、C〜Cアルキルで置換されていてもよいC〜Cシクロアルコキシ、ベンジルオキシ、COORa、−NU、Tで置換されていてもよいフェニル、Tで置換されていてもよいフェノキシ、ナフチル、Tで置換されていてもよいピリジルまたはA−1〜A−140であり、
Rg及びRhは各々独立に、OH、フェニル、C〜Cアルキル、C〜CアルコキシまたはC〜Cアルキルスルフェニルであり、
Ri、Rj及びRkは各々独立に、H、C〜Cアルキル、C〜Cアルケニル、C〜Cアルキル基で置換されていてもよいC〜Cシクロアルキル基またはベンジルであるか、あるいはRi、Rj及びRkのうちの2個が、それぞれが結合している窒素原子と共に酸素原子、窒素原子または硫黄原子を含有していてもよい5ないし8員環基を形成してもよく、
は、ハロゲン、C〜Cアルキル、C〜CハロアルキルまたはC〜Cアルコキシであり、
は、ハロゲンで置換されていてもよいC〜Cアルケニルであり、
は、ハロゲン、C〜Cアルキル、C〜Cハロアルキル、C〜Cアルコキシ、C〜Cハロアルコキシ、C〜Cアルキルスルフェニル、C〜Cアルキルスルフィニル、C〜Cアルキルスルホニル、C〜Cハロアルキルスルフェニル、C〜Cハロアルキルスルフィニル、C〜Cハロアルキルスルホニル、NO、CN、CHO、−NU、フェニル及びフェノキシの中から任意に選ばれる1ないし5個の置換基であり、
及びUは、各々独立に、H、C〜Cアルキル、COORa、フェニルまたはベンジルを表すか、あるいはUとUとが結合している窒素原子と共に酸素原子、窒素原子または硫黄原子を含有していてもよい5ないし8員環基を形成してもよく、
mは、置換基の数を表し、0、1、2または3であり、
nは、置換基の数を表し、0、1、2、3または4であり、
pは、置換基の数を表し、0、1または2であり、
qは、置換基の数を表し、0または1である。(但し、m、n及びpが2以上の整数を表す場合は、その置換基は同一か相互に異なってもよい。)]。
化合物群A:アシベンゾラルーS−メチル、アシルアミノベンザミド、アンバム、アムプロピルホス、アニラジン、アザコナゾール、アゾキシストロビン、ベナラキシル、ベノダニル、ベノミル、ベンチアゾール、ベンザマクリル、ビナパクリル、ビフェニル、ビテルタノール、ベトキサジン、ボルドー液、ブラストサイジン−S、ブロモコナゾール、ブピリメート、ブチオベート、カルシウムポリスルフィド、キャプタフォール、キャプタン、カッパーオキシクロリド、カルプロパミド、カルベンダジン、カルボキシン、CGA−279202、キノメチオネート、クロベンチアゾン、クロルフェナゾール、クロロネブ、クロロタロニル、クロゾリネート、クフラネブ、シモキサニル、シプロコナゾール、シプロジニル、シプロフラム、ダゾメット、デバカルブ、ジクロロフェン、ジクロブトラゾール、ジクロフラニド、ジクロメジン、ジクロラン、ジエトフェンカルブ、ジクロシメット、ジフェノコナゾール、ジフルメトリン、ジメチリモール、ジメトモルフ、ジニコナゾール、ジニコナゾール−M、ジノカップ、ジフェニルアミン、ジピリチオン、ジタリムホス、ジチアノン、ドデモルフ、ドジン、ドラゾクソロン、エデフェノホス、エポキシコナゾール、エタコナゾール、エチリモル、エトリジアノール、ファモキサゾン、フェナリモル、フェブコナゾール、フェナミドン、フェンダゾスラム、フェンフラム、フェンヘキサミド、フェンピクロニル、フェンプロピジン、フェンプロピモルフ、フェンチン、フェルバン、フェリムゾン、フルアジナム、フルジオキソニル、フルオロイミド、フルキンコナゾール、フルシラゾール、フルスルファミド、フルトラニル、フルトリアフォール、フォルペット、フォセチル−アルミニウム、フベリダゾール、フララキシル、フラメトピル、グアザチン、ヘキサクロロベンゼン、ヘキサコナゾール、ヒメキサゾール、イマザリル、イミベンコナゾール、イミノクタジン、イプコナゾール、イプロベンホス、イプロジオン、イソプロチオラン、イプロバリカルブ、カスガマイシン、クレソキシム−メチル、マンカッパー、マンコゼブ、マンネブ、メパニピリム、メプロニル、メタラキシル、メトコナゾール、メタスルホカルブ、メチラム、メトミノストロビン、ミクロブタニル、MTF−753、ナバム、ニッケルビス(ジメチルジチオカーバメート)、ニトロタール−イソプロピル、ヌアリモル、NNF−9425、オクチリノン、オフレース、オキサジキシル、オキシカルボキシン、オキポコナゾールフマール酸塩、ペフラゾエート、ペンコナゾール、ペンシクロン、フタライド、ピペラリン、ポリオキシン、炭酸水素カリウム、プロベナゾール、プロクロラズ、プロシミドン、プロパモカルブ塩酸塩、プロピコナゾール、プロピネブ、ピラゾホス、ピリフェノックス、ピリメタニル、ピロキュロン、キノメチオネート、キノキシフェン、キントゼン、RH7281、炭酸水素ナトリウム、次亜塩素酸ナトリウム、硫黄、スピロキサミン、テブコナゾール、テクナゼン、テトラコナゾール、チアベンダゾール、チアジアジン、チフルザミド、チオファネート−メチル、チラム、トルクロホス−メチル、トリルフラニド、トリアジメホン、トリアジメノール、トリアゾキシド、トリシクラゾール、トリデモルフ、トリフルミゾール、トリホリン、トリチコナゾール、バリダマイシン、ビンクロゾリン、硫酸亜鉛、ジネブ、ジラム、シイタケ菌糸体抽出物、ストレプトマイシン、テクロフタラム、オキシテトラサイクリン、オキソリニックアシド、アルドキシカルブ、カズサホス、フォスチアゼート、フォスチエタン、オキサミル、フェナミホス、アセキノシル、ブロモプロピレート、チノメチオネート、クロロベンジラート、サイヘキサチン、ジコフォール、ジエノクロール、エトキサゾール、フェナザキン、フェンブタチンオキシド、フェンプロパトリン、フェンプロキシメート、ハルフェンプロックス、ヘキシチアゾックス、ミルベメクチン、プロパルギット、ピリダベン、ピリミジフェン、テブフェンピラド、アバメクチン、アセフェート、アセタミピリド、アルディカルブ、アレスリン、アジンホス−メチル、ベンジオカルブ、ベンフラカルブ、ベンスルタップ、ブプロフェジン、ブトカルボキシン、カルバリル、カルボフラン、カルボスルファン、カルタップ、クロルフェナピル、クロルピリホス、クロルフェンビンホス、クロルフルアズロン、クロチアニジン、クロマフェノジド、クロピリホス−メチル、シクロプロトリン、シフルトリン、ベータ−シフルトリン、シペルメトリン、シロマジン、シハロトリン、ラムダ−シハロトリン、デルタメトリン、ジアフェンチウロン、ダイアジノン、ジアクロデン、ジフルベンズロン、ジメチルビンホス、ジオフェノラン、ジスルフォトン、ジメトエート、エマメクチンベンゾエート、EPN、エスフェンバレレート、エチオフェンカルブ、エチプロール、エトフェンプロックス、エトリムホス、フェニトロチオン、フェノブカルブ、フェノキシカーブ、フェンプロパトリン、フェンバレレート、フィプロニル、フルアクリピリム、フルシトリネート、フルフェノクスウロン、フルフェンプロックス、タウ−フルバリネート、ホノホス、フォルメタネート、フォルモチオン、フラチオカルブ、ハロフェノジド、ヘキサフルムロン、ヒドラメチルノン、イミダクロプリド、イソフェンホス、インドキサカルブ、イソプロカルブ、イソキサチオン、ルフェヌウロン、マラチオン、メタルデヒド、メタミドホス、メチダチオン、メタクリホス、メタルカルブ、メソミル、メソプレン、メトキシクロール、メトキシフェノジド、モノクロトホス、ムスカルーレ、ニジノテフラン、ニテンピラム、オメトエート、オキシデメトン−メチル、オキサミル、パラチオン、パラチオン−メチル、ペルメトリン、フェントエート、フォキシム、ホレート、ホサロン、ホスメット、ホスファミドン、ピリミカルブ、ピリミホス−メチル、プロフェノホス、プロトリフェンブト、ピメトロジン、ピラクロホス、ピリプロキシフェン、ロテノン、スルプロホス、シラフルオフェン、スピノサド、スルホテップ、テブフェノジド、テフルベンズロン、テフルトリン、テルブホス、テトラクロロビンホス、チアクロプリド、チオシクラム、チオジカルブ、チアメトキサム、チオファノックス、チオメトン、トルフェンピラド、トラロメスリン、トリクロルホン、トリアズロン、トリフルムロン、バミドチオン及びエチオン。
An insecticidal, acaricidal, nematicidal, bactericidal or bactericidal composition containing at least one acrylonitrile compound represented by the following formula (1) and at least one compound selected from the following compound group A.
Equation (1):
Figure 2004155693
[Where A is
Figure 2004155693
Figure 2004155693
Figure 2004155693
Figure 2004155693
Figure 2004155693
And
B is H, CR 1 R 2 R 3 , CHR 1 R 2 , C 1 -C 4 haloalkyl, tetrahydropyranyl, Si (CH 3 ) 3 , SO 2 Re, SO 2 NHRb, SO 2 NRaRb, C (S ) NHRb, C (S) NRaRb, C (O) Rf, P (O) RgRh, P (S) RgRh, an alkali metal, an alkaline earth metal or NHRiRjRk;
G is, H, halogen, C 1 -C 6 alkyl, C 1 -C 4 alkyl substituted by Rc, C 1 ~C 4 haloalkyl, C 1 -C 3 alkyl C 3 optionally substituted with -C 6 cycloalkyl, C 1 -C 6 alkoxy, C 2 -C 4 alkenyloxy, C 2 -C 4 alkynyloxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylsulfenyl, C 1 -C 4 alkyl sulfinyl, C 1 -C 4 alkylsulfonyl, C 2 -C 4 alkenyl Le phenyl, C 2 -C 4 alkenylsulfinyl, C 2 -C 4 alkenylsulfonyl, C 2 -C 4 alkyl Nils Le phenyl, C 2 -C 4 alkynyl sulfinyl, C 2 -C 4 alkynylsulfonyl, C 1 -C 4 haloalkylsulfenyl, C 1 -C 4 haloalkylsulfenyl Iniru, C 1 -C 4 haloalkylsulfonyl, C 2 -C 4 halo alkenyl Le phenyl, C 2 -C 4 halo alkenylsulfinyl, C 2 -C 4 haloalkenyl sulfonyl, NO 2, CN, -NU 1 U 2, naphthyl , Rc-substituted methoxy, C 2 -C 5 alkoxycarbonyl, C 2 -C 4 alkoxyalkyl, C 2 -C 4 alkylcarbonyl, C 2 -C 4 haloalkylcarbonyl, C 2 -C 5 alkylcarbonyloxy, C 2 -C 5 halo alkylcarbonyloxy, C 3 -C 7 dialkylaminocarbonyloxy, phenyl optionally substituted by Z, which may be substituted with Z phenoxy, optionally substituted by Z benzoyl, with Z Pyridyl which may be substituted, pyridylo which may be substituted by Z Shi, thienyl which may be substituted with Z, adjacent methylenedioxy bound to a substituted position, to 1 selected from halo methylenedioxy and -N = CT 2 T 3 bound in adjacent substitution positions 4 A 5- to 8-membered ring formed by two substituents or an alkylene group bonded at an adjacent substituent position;
Y, Y 1 and Y 2 are each independently H, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylsulfenyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfenyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, NO 2 or CN A 5-, 6-, 7- or 8-membered ring formed by an alkylene group which is present or is attached at an adjacent substituent position;
Y 3 is H, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;
Z is each independently halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylsulfenyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 2 -C 4 alkenyl Le phenyl, C 2 -C 4 alkenylsulfinyl, C 2 -C 4 alkenylsulfonyl, C 1 -C 4 haloalkylsulfenyl, C 1 -C 4 haloalkylsulfinyl, a C 1 -C 4 haloalkylsulfonyl, nO 2, CN, 1 to 5 substituents selected from among -NU 1 U 2 and C 2 -C 5 alkoxycarbonyl,
R 1 , R 2 , R 3 and Ra are each independently C 1 -C 6 alkyl;
Rb is, H, a C 1 -C 6 alkyl or phenyl optionally substituted with T 1,,
Rc is halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy and C 1 -C 4 phenyl optionally substituted with one or more selected arbitrarily from among haloalkyl,
Rd is benzoyl optionally substituted with one or more selected from halogen, C 1 -C 4 alkyl and C 1 -C 4 haloalkyl,
Re is C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, or phenyl optionally substituted with T 1 ,
Rf is, C 1 -C 20 alkyl, C 2 -C 6 alkenyl, C 1 -C 6 haloalkyl, C 2 -C 4 alkoxyalkyl, C 3 -C 6 halocycloalkyl, C 1 -C substituted with Rc 4 alkyl, C 1 -C 4 optionally substituted by alkyl C 3 -C 7 cycloalkyl, cycloalkyl substituted with Rc, Rc and C 1 -C 4 alkyl substituted cyclopropyl, Rc and halogen A C 3 -C 4 cycloalkyl group substituted with T 2 and a C 1 -C 4 alkyl-substituted cyclopropyl group, a R 2 -substituted C 2 -C 4 alkenyl, a C 1 -C 6 alkoxy, 1 -C 4 haloalkoxy, C 2 -C 5 alkenyloxy, C 1 -C 3 may be alkyl substituted C 3 -C 6 cycloalkoxy, benzyloxy , COORa, -NU 1 U 2 , phenyl optionally substituted with T 3 , phenoxy optionally substituted with T 3 , naphthyl, pyridyl optionally substituted with T 1 or A-1 to A- 140,
Rg and Rh are each independently, OH, phenyl, C 1 -C 6 alkyl, C 1 -C 6 alkoxy or C 1 -C 4 alkylsulfenyl,
Ri, Rj and Rk each independently represent H, C 1 -C 6 alkyl, C 1 -C 4 alkenyl, C 3 -C 6 cycloalkyl group optionally substituted with C 1 -C 3 alkyl group or benzyl Or two of Ri, Rj and Rk together with the nitrogen atom to which each is attached form a 5- to 8-membered ring group which may contain an oxygen, nitrogen or sulfur atom May be
T 1 is halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 1 -C 4 alkoxy;
T 2 is C 2 -C 4 alkenyl optionally substituted with halogen,
T 3 is halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylsulfenyl, C 1 -C 4 alkyl sulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfenyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, NO 2, CN, CHO, -NU 1 U 2, phenyl and 1 to 5 substituents arbitrarily selected from phenoxy,
U 1 and U 2 each independently represent H, C 1 -C 6 alkyl, COORa, phenyl or benzyl, or together with the nitrogen atom to which U 1 and U 2 are bonded, an oxygen atom, a nitrogen atom or It may form a 5- to 8-membered ring group which may contain a sulfur atom,
m represents the number of substituents, and is 0, 1, 2, or 3,
n represents the number of substituents, and is 0, 1, 2, 3, or 4;
p represents the number of substituents, and is 0, 1 or 2,
q represents the number of substituents and is 0 or 1. (However, when m, n and p represent an integer of 2 or more, the substituents may be the same or different from each other.)].
Compound group A: acibenzolar-S-methyl, acylaminobenzamide, ambam, ampropylphos, anilazine, azaconazole, azoxystrobin, benalaxyl, benodanil, benomyl, benzazole, benzamacril, binapacryl, biphenyl, vitertanol, vetoxazine, bordeaux solution, Blasticidin-S, bromoconazole, bupurimate, butiobate, calcium polysulfide, captafall, captan, kappa oxychloride, carpropamide, carbendazine, carboxin, CGA-279202, quinomethionate, clobenzazone, chlorphenazole, chloroneb , Chlorothalonil, clozolinate, kufuraneb, simoxanil, cyproconazole, cyprodinil, cyprofuram, daphne Met, debacarb, dichlorophen, diclobutrazol, diclofuranide, diclomedine, dichlorane, dietofencarb, diclosimet, difenoconazole, diflumethrin, dimethilimol, dimethomorph, diniconazole, diniconazole-M, dinocap, diphenylamine, dipyridiondine, ditaminido, thitarimidine, ditathiodionide, ditaminone Drazoxolone, edefenophos, epoxyconazole, etaconazole, etirimol, etridianol, famoxazone, fenarimol, febuconazole, phenamidone, fendazoslam, fenfuram, fenhexamide, fenpiclonil, fenpropidin, fenpropimorph, fentin, felvan, ferimzone, Fluazinam, Fludioxonil, F Oroimide, Fluquinconazole, Flusilazole, Flusulfamide, Flutranil, Flutriafol, Folpetol, Focetyl-aluminum, Feveridazole, Furalaxyl, Flamethopyr, Guazatine, Hexachlorobenzene, Hexaconazole, Himexazole, Imazalil, Imibenconazole, Iminoctazine, Ipconazole, Iprovenphos, iprodione, isoprothiolane, iprovalicarb, kasugamycin, kresoxim-methyl, mancapper, mancozeb, manneb, mepanipyrim, mepronil, metalaxyl, metconazole, metasulfocarb, metyram, metominostrobin, microbutanyl, MTF-753, nabam, nickel Dimethyldithiocarbamate), nitrotar-isopro Pill, Nuarimol, NNF-9425, Octylinone, Offrace, Oxazixyl, Oxycarboxin, Okopconazole Fumarate, Pefurazoate, Penconazole, Pencyclon, Phthalide, Piperalin, Polyoxin, Potassium Bicarbonate, Probenazole, Prochloraz, Procymidone, Propamocarb Hydrochloride Salt, propiconazole, propineb, pyrazophos, pyrifenox, pyrimethanil, pyrocuron, quinomethionate, quinoxyfen, quintozen, RH7281, sodium bicarbonate, sodium hypochlorite, sulfur, spiroxamine, tebuconazole, technazen, tetraconazole, thiabendazole, Thiadiazine, thifluzamide, thiophanate-methyl, thiram, tolclofos-methyl, tolylfurani , Triadimefon, triadimenol, triazoxide, tricyclazole, tridemorph, triflumizole, triforine, triticonazole, validamycin, vinclozolin, zinc sulfate, zineb, ziram, shiitake mushroom mycelium extract, streptomycin, teclophthalam, oxytetracycline, oxolinic acid, Aldoxycarb, Kazusaphos, Fostiazate, Fostietan, Oxamyl, Fenamiphos, Acequinosyl, Bromopropylate, Tinomethionate, Chlorobenzylate, Cyhexatin, Dicophor, Dienochlor, Ethoxazole, Fenazaquin, Fenbutatin oxide, Fenpropatrin, Fenproximate, Hull Fenprox, Hexythiazox, Milbemectin, Propal , Pyridaben, pyrimidifen, tebufenpyrad, abamectin, acephate, acetamipyride, aldicarb, alesulin, azinphos-methyl, bendiocarb, benflacarb, bensultap, buprofezin, butocarboxin, carbaryl, carbofuran, carbosulfan, cartap, chlorfenapyr, chlorfenapyr Chlorfenvinphos, chlorfluazuron, clothianidin, chromafenozide, clopyrifos-methyl, cycloprothrin, cyfluthrin, beta-cyfluthrin, cypermethrin, cyromazine, cyhalothrin, lambda-cyhalothrin, deltamethrin, diafenthiuron, diazinon, diacloden, Diflubenzuron, dimethylvinphos, diphenolane, disulfotone, Methoate, emamectin benzoate, EPN, esfenvalerate, ethiophencarb, ethiprole, etofenprox, etrimphos, fenitrothion, fenobcarb, phenoxycarb, fenpropatrin, fenvalerate, fipronil, fluacryliprim, flucitrinate, flufenoxuron, flufenprox , Tau-fluvalinate, honofos, formetanate, formothion, flatiothiocarb, halofenozide, hexaflumuron, hydramethylnon, imidacloprid, isofenphos, indoxacarb, isoprocarb, isoxathion, lufenuuron, malathion, metaldehyde, methamidophos, methacrylthione, methacrylthione Metal carb, mesomeril, mesoprene, methoki Chlor, methoxyphenozide, monocrotophos, muscarule, nidinotefuran, nitenpyram, omethoate, oxydemethone-methyl, oxamyl, parathion, parathion-methyl, permethrin, fentoate, foxime, holate, hosalon, phosmet, phosphamidon, pirimicarb, pirimiphos-methyl, proferinophos-methyl. Protrifenbute, pymetrozine, pyraclophos, pyriproxyfen, rotenone, sulprofos, silafluofen, spinosad, sulfotep, tebufenozide, teflubenzuron, tefluthrin, terbufos, tetrachlorovinphos, thiacloprid, thiocyclam, thiodicarb, thiamethoxam, thiophanox, thiometon Tolfenpyrad, Tralomethrin, Trichlor Down, Toriazuron, triflumuron, vamidothion and ethion.
請求項1記載の式(1)で表されるアクリロニトリル化合物の1種以上と、以下の化合物群Bより選ばれる化合物の1種以上を含有する殺ダニ組成物。
化合物群B:アセキノシル、ブロモプロピレート、チノメチオネート、ジコフォール、エトキサゾール、フェンブタチンオキシド、ミルベメクチン、プロパルギット、ピリダベン、アバメクチン、アルディカルブ、クロルピリフォス、ジフルベンズロン、クロルフェナピル、フェントエート、エマメクチンベンゾエート、メチダチオン、オキサミル、カルシウムポリスルフィド、マンコゼブ、マンネブ及びエチオン。
An acaricidal composition comprising at least one acrylonitrile compound represented by the formula (1) according to claim 1 and at least one compound selected from the following compound group B.
Compound group B: acequinosyl, bromopropylate, tinomethionate, dicophor, ethoxazole, fenbutatin oxide, milbemectin, propargite, pyridaben, abamectin, aldicarb, chlorpyrifos, diflubenzuron, chlorfenapyr, fentoate, emamectin benzoate, methidathione Polysulfide, Mancozeb, Maneb and Ethion.
ハダニ、フシダニ又はホコリダニの防除に用いる請求項2記載の殺ダニ組成物。3. The acaricidal composition according to claim 2, which is used for controlling spider mites, dust mites or dust mites. 請求項1記載の式(1)で表されるアクリロニトリル化合物の1種以上と、請求項1記載の化合物群Aより選ばれる化合物の1種以上を同時に、又は近接して処理することを特徴とする、害虫又は病害の防除方法。The method is characterized in that one or more acrylonitrile compounds represented by the formula (1) according to claim 1 and one or more compounds selected from the compound group A according to claim 1 are treated simultaneously or in close proximity. To control pests or diseases. 請求項1記載の式(1)で表されるアクリロニトリル化合物の1種以上と、請求項2記載の化合物群Bより選ばれる化合物の1種以上を同時に、又は近接して処理することを特徴とする、ダニの防除方法。The method is characterized in that one or more acrylonitrile compounds represented by the formula (1) according to claim 1 and one or more compounds selected from the compound group B according to claim 2 are treated simultaneously or in close proximity. How to control mites. 請求項1記載の式(1)で表されるアクリロニトリル化合物の1種以上と、請求項2記載の化合物群Bより選ばれる化合物の1種以上を同時に、又は近接して処理することを特徴とする、ハダニ、フシダニ又はホコリダニの防除方法。The method is characterized in that one or more acrylonitrile compounds represented by the formula (1) according to claim 1 and one or more compounds selected from the compound group B according to claim 2 are treated simultaneously or in close proximity. A method for controlling spider mites, spider mites or dust mites.
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CN109553577A (en) * 2018-12-20 2019-04-02 西安近代化学研究所 A kind of pyrazole compound and preparation method and application
CN109744241A (en) * 2018-12-28 2019-05-14 京博农化科技有限公司 A kind of miticide composition of containing fluazinam and nitrile pyrrole mite rouge
CN110269064A (en) * 2018-03-13 2019-09-24 江苏扬农化工股份有限公司 A kind of miticide composition of fluazinam and nitrile pyrrole mite ester compounding
CN114431237A (en) * 2020-11-03 2022-05-06 浙江省化工研究院有限公司 Pesticide composition

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JP5339055B2 (en) * 2006-06-13 2013-11-13 日産化学工業株式会社 Aqueous suspension pesticide composition
WO2007145221A1 (en) * 2006-06-13 2007-12-21 Nissan Chemical Industries, Ltd. Aqueous suspension agricultural chemical composition
JP2016065093A (en) * 2006-07-06 2016-04-28 バイエル・クロップサイエンス・アクチェンゲゼルシャフト Pesticide composition containing pyridyl ethyl benzamide derivative and insecticidal compound
JP2014012686A (en) * 2006-07-06 2014-01-23 Bayer Cropscience Ag Pesticide composition comprising pyridylethylbenzamide derivative and insecticidal compound
US9408385B2 (en) 2006-07-06 2016-08-09 Bayer Cropscience Ag Pesticidal composition comprising a pyridylethylbenzamide derivative and an insecticide compound
WO2010095427A1 (en) 2009-02-17 2010-08-26 株式会社日本触媒 Polyacrylic acid-based water-absorbing resin powder and method for producing the same
CN104904722A (en) * 2015-05-19 2015-09-16 陕西上格之路生物科学有限公司 Mite killing composition containing cyenopyrafen and pyridaben
CN104920393A (en) * 2015-05-19 2015-09-23 陕西上格之路生物科学有限公司 Acaricidal composition containing cyenopyrafen and abamectin
CN107912436A (en) * 2017-12-06 2018-04-17 广东中迅农科股份有限公司 A kind of composition pesticide of the mite ester of pyrrole containing nitrile and fluazinam
CN110269064A (en) * 2018-03-13 2019-09-24 江苏扬农化工股份有限公司 A kind of miticide composition of fluazinam and nitrile pyrrole mite ester compounding
CN109553577A (en) * 2018-12-20 2019-04-02 西安近代化学研究所 A kind of pyrazole compound and preparation method and application
CN109744241A (en) * 2018-12-28 2019-05-14 京博农化科技有限公司 A kind of miticide composition of containing fluazinam and nitrile pyrrole mite rouge
CN114431237A (en) * 2020-11-03 2022-05-06 浙江省化工研究院有限公司 Pesticide composition

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