JP4038624B2 - Fused heterocyclic derivatives and intermediates thereof, and pest control agents - Google Patents
Fused heterocyclic derivatives and intermediates thereof, and pest control agents Download PDFInfo
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- JP4038624B2 JP4038624B2 JP34449797A JP34449797A JP4038624B2 JP 4038624 B2 JP4038624 B2 JP 4038624B2 JP 34449797 A JP34449797 A JP 34449797A JP 34449797 A JP34449797 A JP 34449797A JP 4038624 B2 JP4038624 B2 JP 4038624B2
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- alkylthio
- alkyl
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- 125000000623 heterocyclic group Chemical group 0.000 title claims description 33
- 241000607479 Yersinia pestis Species 0.000 title claims description 27
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Description
【０００１】
【発明の属する技術分野】
本発明は、有害生物防除剤として有用な新規な縮合複素環誘導体及びその用途並びにその中間体に関するものである。
【０００２】
【従来の技術】
特開平１−１３２５８０号公報、同２−２９０８７１号公報、同６−２３４７４８号公報及び同８−３２５２３９号公報にトリアジノン誘導体、イミダゾール誘導体又はキナゾリン誘導体が有害生物防除剤として有用であることが開示されている。
【０００３】
【発明が解決しようとする課題】
本発明者等は新規な有害生物防除剤を創出すべく鋭意研究を重ねた結果、本発明の一般式(I) で表される複素環誘導体及び該化合物を製造するための中間体である一般式(II)で表される化合物は文献未記載の新規化合物であり、更に一般式(I) で表される複素環誘導体は各種害虫に対して低薬量で優れた効果を有するものであることを見出し、本発明を完成させたものである。
【０００４】
【課題を解決するための手段】
本発明は一般式(I)
【化３】
【０００５】
フェニルC1-C3 アルキル基、同一又は異なっても良く、ハロゲン原子、C1-C3 アルキル基、ハロC1-C3 アルキル基、C1-C3 アルコキシ基、ハロC1-C3 アルコキシ基、C1-C3 アルキルチオ基又はハロC1-C3 アルキルチオ基から選択される１〜３個の置換基を環上に有するフェニルC1-C3 アルキル基、フェニルカルボニル基、又は同一若しくは異なっても良く、ハロゲン原子、C1-C3 アルキル基、ハロC1-C3 アルキル基、C1-C3 アルコキシ基、ハロC1-C3 アルコキシ基、C1-C3 アルキルチオ基、又はハロC1-C3 アルキルチオ基から選択される１〜３個の置換基を環上に有するフェニルカルボニル基を示す。
【０００６】
Ｒ1 及びＲ2 はお互いに一緒になって、同一又は異なっても良い酸素原子、硫黄原子又は窒素原子から選択される１〜３個のヘテロ原子により中断された５〜６員複素環を示し、Ｘは同一又は異なっても良く、水素原子、ハロゲン原子、シアノ基、ニトロ基、C1-C3 アルキル基、ハロC1-C3 アルキル基、 C2-C4アルケニル基、ハロC2-C4 アルケニル基、 C2-C4アルキニル基、ハロC2-C4 アルキニル基、C1-C3 アルコキシ基、ハロC1-C3 アルコキシ基、C1-C3 アルキルチオ基、又はハロC1-C3 アルキルチオ基から選択される置換基を示す。ｎは０〜３の整数を示す。
【０００７】
Ａは-NH-CH2-又は-N=CH-を示し、Ｒ3 はピリジル基又はそのＮ−オキシド基、同一又は異なっても良く、ハロゲン原子、シアノ基、ニトロ基、C1-C3 アルキル基、ハロC1-C3 アルキル基、C1-C3 アルコキシ基、ハロC1-C3 アルコキシ基、C1-C3 アルキルチオ基又はハロC1-C3 アルキルチオ基から選択される１〜３個の置換基を有するピリジル基又はそのＮ−オキシド基、チアゾール基、又は同一若しくは異なっても良く、ハロゲン原子、シアノ基、ニトロ基、C1-C3 アルキル基、ハロC1-C3 アルキル基、C1-C3 アルコキシ基、ハロC1-C3 アルコキシ基、C1-C3 アルキルチオ基、又はハロC1-C3 アルキルチオ基から選択される１〜３個の置換基を有するチアゾール基を示す。〕
で表される縮合複素環誘導体及び該縮合複素環誘導体を有効成分として含有する有害生物防除剤、並びに該縮合複素環誘導体を製造するための中間体化合物である一般式(II)
【０００８】
【化４】
で表される化合物に関するものである。
【０００９】
本発明の一般式(I) で表される縮合複素環誘導体又はその塩は、その化学構造上、互変異性体を有するものであり、本発明はこれらの互変異性体も包含するものである。また、これらの化合物と無機または有機の酸との塩も包含するものである。
【００１０】
【発明の実施の形態】
本発明の一般式(I) で表される縮合複素環誘導体は、その各置換基の定義中、『ハロゲン原子』とは塩素原子、臭素原子、ヨウ素原子またはフッ素原子を示し、『C1-C3 アルキル基』とは、炭素原子数１〜３の直鎖状又は分枝状のアルキル基を示し、例えばメチル、エチル、ｎ−プロピル、ｉ−プロピル等を示すものとする。『ハロC1-C3 アルキル基』とは、１以上の同一又は異なっても良いハロゲン原子で置換された炭素原子数１〜３の直鎖状又は分枝状のアルキル基を示し、『C2-C4 アルケニル基』とは、１以上の２重結合を有する炭素原子数２〜４の直鎖状又は分枝状のアルケニル基を示し、例えばビニル、アリル、イソプロペニル、１−メチルプロペニル、１−ブテニル、２−ブテニル、３−ブテニル等を示し、『ハロC2-C4 アルケニル基』とは、１以上の同一又は異なっても良いハロゲン原子で置換された炭素原子数２〜４の直鎖状又は分枝状のアルケニル基を示す。『C2-C4 アルキニル基』とは、１以上の３重結合を有する炭素原子数２〜４の直鎖状又は分枝状のアルキニル基を示し、例えば、エチニル、２−プロピニル、１−メチル−２−プロピニル、１−ブチニル、２−ブチニル、３−ブチニル等を示し、『ハロC2-C4 アルキニル基』とは、１以上の同一又は異なっても良いハロゲン原子で置換された炭素原子数２〜４の直鎖状又は分枝状のアルキニル基を示し、
【００１１】
『同一又は異なっても良い酸素原子、硫黄原子又は窒素原子から選択される１〜３個のヘテロ原子により中断された５〜６員複素環』とは、例えば、フラン、チオフェン、ピロール、オキサゾール、イソキサゾール、チアゾール、イソチアゾール、ピラゾール、イミダゾール、１，２，３−チアジアゾール、ピリジン、ピリダジン、ピリミジン、ピラジン等の５〜６員環を示すものとする。
【００１２】
本発明の一般式(I) で表される縮合複素環誘導体は、例えば下記に示す製造方法により、中間体である一般式(II)で表される化合物を経て製造することができる。
まず、本発明の中間体である一般式(II)で表される化合物は、例えば下記に示す製造方法により製造することができる。
【００１３】
製造方法１．
【化５】
【００１４】
一般式(IX)で表される化合物と一般式(VIII)で表される化合物とを不活性溶媒及び触媒の存在下に反応させて一般式(VII) で表される化合物とし、該化合物(VII) を単離し又は単離せずして還元反応を行い、一般式(VI)で表される化合物とし、該化合物(VI)を単離し又は単離せずして環化反応を行い、一般式(V) で表される化合物とし、該化合物(V) を単離し又は単離せずして加水分解反応を行うことにより一般式(II)で表される化合物を製造することができる。
本反応は特開平８−３２５２３９号公報に開示の製造方法に準じて製造することができる。
【００１５】
上記反応の出発物質である一般式(IX)で表される化合物は公知の方法に準じて得られ、例えばＪ．Ｃｈｅｍ．Ｓｏｃ．，１０４５（１９５６）、Ｊ．Ｃｈｅｍ．Ｓｏｃ．，１３７２（１９６０）、Ｊ．Ｃｈｅｍ．Ｓｏｃ．，３８６（１９４３）、Ｂｅｒ．，１００，３６６４（１９６７）等の方法に準じて合成される。
【００１６】
以下に本発明の一般式（II) で表される化合物の代表例を第１表に例示するが、本発明はこれらに限定されるものではない。
一般式（II）
【化６】
【表１】
【表２】
次に本発明の一般式(I）で表される縮合複素環誘導体又はその塩の代表的な製造方法を以下に図式的に示す。
製造方法２．
【化７】
【００２０】
先に製造方法１で得られた一般式(II)で表される化合物を一般式(IV)で表される化合物と反応させることにより一般式(I-1) で表される縮合複素環誘導体を製造し、さらに該縮合複素環誘導体(I-1) と一般式(III) で表されるハライド類とを反応させることにより、一般式(I-2) で表される縮合複素環誘導体を製造することができる。
又、得られた一般式(I-1) で表される縮合複素環誘導体を還元反応することにより、一般式(I-3) で表される縮合複素環誘導体を製造することができる。
本反応は特開平８−３２５２３９号公報に開示の製造方法に準じて製造することができる。
【００２１】
以下に本発明の一般式(I) で表される縮合複素環誘導体又はその塩類の代表例を第２表に例示するが、本発明はこれらに限定されるものではない。
一般式(I）
【化８】
【表３】
【表４】
【実施例】
以下に本発明の代表的な実施例を示すが、本発明はこれらに限定されるものではない。
実施例１． ３，４−ジヒドロ−３−（ピリジルメチリデンアミノ）−ピリド〔２，３−ｄ〕ピリミジン−２−オンの製造
【化９】
１−１． ｔ−ブチル ２−（２−アミノピリジル−３─メチリデン）カルバジン酸の製造
２．３０ｇ（１８．８ミリモル）の２−アミノピリジン−３−アルデヒドと２．４８ｇ（１８．８ミリモル）のｔ−ブチルカルバジン酸及び１滴の酢酸を２０ｍｌのメタノ─ルに加え、５時間加熱還流下に反応を行った。反応終了後、溶媒を減圧下に留去し、析出した結晶を濾集して目的物４ｇを得た。
1H-NMR[CDCl3/TMS、δ値(ppm)]
1.45(s,9H), 6.60(dd,1H), 7.4(brs,2H), 7.45(dd,1H), 7.95(dd,1H), 8.00(brs,1H), 11.0(brs,1H)
収率：９０％
【００２６】
１−２． ｔ−ブチル ２−（２−アミノピリジル−３─メチル）カルバジン酸の製造
１−１で得られたｔ−ブチル ２−（２−アミノピリジル−３─メチリデン）カルバジン酸２ｇ（８．５ミリモル）と０．２ｇの５％パラジウムカーボンを２０ｍｌの酢酸中に加え、４〜５ｋｇ／ｍ2 で接触還元を行った。水素吸収が止まった後、触媒を濾去し、溶媒を減圧下に留去して目的物２．０ｇを得た。
1H-NMR[CDCl3/TMS、δ値(ppm)]
1.46(s,9H), 3.95(d,2H), 4.05(brs,1H), 5.35(brs,2H), 6.10(brs,1H), 6.60(dd,1H), 7.30(dd,1H), 8.02(dd,1H)
収率：定量的
【００２７】
１−３． ３，４−ジヒドロ−３−（ｔ−ブトキシカルボニルアミノ）−ピリド〔２，３─ｄ〕ピリミジン−２−オンの製造。
１−２で得られたｔ−ブチル ２−（２−アミノピリジル−３─メチル）カルバジン酸２ｇ（８．５ミリモル）と１．３８ｇ（８．５ミリモル）の１，１’−カルボニルビス−１Ｈ−イミダゾール（ＣＤＩ）を２０ｍｌの乾燥したテトラヒドロフラン中に溶解し、５時間加熱還流下に反応を行った。反応終了後、反応液を３０ｍｌの水に注ぎ、目的物をクロロホルム各３０ｍｌで３回抽出した。合した抽出液を、飽和食塩水で洗浄して無水硫酸マグネシウムで乾燥後、溶媒を減圧下に留去し、残渣を酢酸エチルで結晶化して目的物０．８ｇを得た。
1H-NMR[CDCl3/TMS、δ値(ppm)]
1.50(s,9H), 4.76(S,1H), 6.78(brs,1H), 6.98(dd,1H), 7.37(d,1H), 8.21( d,1H), 8.75(brs,1H)
収率：３５％
【００２８】
１−４． ３，４−ジヒドロ−３−アミノ−ピリド〔２，３−ｄ〕ピリミジン−２−オンの製造
１−３で得られた３，４−ジヒドロ−３−（ｔ−ブトキシカルボニルアミノ）−ピリド〔２，３−ｄ〕ピリミジン−２−オン０．８ｇ（３ミリモル）を５ｍｌのトリフルオロ酢酸中に０℃で加え、その後室温にて１時間反応させた。反応終了後溶媒を減圧下に留去し、残渣をエタノールで再結晶化して目的物０．３５ｇを得た。
1H-NMR[CDCl3/TMS、δ値(ppm)]
4.0〜4.5(brS,2H), 4.57(s,1H), 6.99(dd,1H), 7.64(d,1H), 8.13(d,1H)
10.34(brs,1H)
収率：７１％
【００２９】
１−５． ３，４−ジヒドロ−３−（ピリジルメチリデンアミノ）−ピリド〔２，３−ｄ〕ピリミジン−２−オンの製造
１−４で得られた３，４−ジヒドロ−３−アミノ−ピリド〔２，３−ｄ〕ピリミジン−２−オン０．３ｇ（１．８ミリモル）と０．２ｇ（１．８ミリモル）のニコチン酸アルデヒド及び１滴の硫酸を１０ｍｌのメタノールに加え、３時間加熱還流下に反応させた。反応終了後、反応液を室温に冷却し、析出した結晶を濾集し、目的物０．３５ｇを得た。
物性：ｍ．ｐ．２５３．２〜２５５．０℃
1H-NMR[DMSO-d6/TMS、δ値(ppm)]
2.50(S,3H), 4.95(s,2H), 7.5(dd,1H), 8.11(S,1H), 8.16(m,1H), 8.39(s,1H), 8.62(m,1H), 8.90(d,1H), 10.75(brs,1H)
収率：７６％
【００３０】
本発明の一般式（Ｉ）で表される縮合複素環誘導体を有効成分とする有害生物防除剤は水稲、野菜、果樹、その他の作物及び花卉等を加害する各種農林、園芸、貯穀害虫や衛生害虫或いは線虫等の害虫防除に適しており、例えばチャノミドリヒメヨコバイ(Empoasca brassicae)、ツマグロヨコバイ(Nephotettix cinticeps) 、トビイロウンカ(Nilaparvata lugens)、セジロウンカ(Sogatella furcifera) 、ミカンキジラミ(Diaphorina citri)、ミカンコナジラミ(Dialeurodes citri) 、タバココナジラミ(Bemicia tabaci)、オンシツコナジラミ(Trialeurodes vaporariorum) 、ダイコンアブラムシ(Brevicoryne brassicae) 、ワタアブラムシ(Aphis gossipii)、ムギクビレアブラムシ(Rhopalosiphum padi)、モモアカアブラムシ(Myzus persicae)、ツノロウムシ(Ceroplastes cerciferus)、ミカンワタカイガラムシ(Pulvinaria aurantii) 、ミカンマルカイガラムシ(Pseudaonidia duplex) 、ナシマルカイガラムシ(Comstockaspis perniciosa)、ヤノネカイガラムシ(Unaspis yanonensis)、等の半翅目害虫、
【００３１】
ミナミネグサレセンチュウ(Pratylenchus coffeae)、ジャガイモシストセンチュウ(Globodera rostochiensis) 、ネコブセンチュウ(Meloidogyne sp.) 、ミカンネセンチュウ(Tylenchulus semipenetrans) 、ニセネグサレセンチュウ(Aphelenchus avenae)、ハガレセンチュウ(Aphelenchoides ritzemabosi)等のハリセンチュウ目に対しても殺虫効果を有するものである。尚、学名等は農林有害動物・昆虫名鑑1987年版（日本応用動物昆虫学会編）による。
【００３２】
本発明の一般式（Ｉ）で表される縮合複素環誘導体またはその塩類を有効成分として含有する有害生物防除剤は水稲、野菜、果樹、その他の作物及び花卉等を加害する前記害虫或いは衛生害虫に対して顕著な殺虫活性を有するものであるので、害虫類の発生が予測される時期に合わせて、害虫類の発生前又は発生が確認された時点で水稲、果樹、野菜その他の作物、花卉等に対し水田水、茎葉又は土壌等及び衛生害虫にあっては人畜に加害する家屋内、家屋周辺の溝等に処理することにより本発明の殺虫剤の所期の効果が奏せられるものであるが、本発明はこれらの態様のみに限定されるものではない。
【００３３】
本発明の一般式（Ｉ）で表される縮合複素環誘導体またはその塩類を有害生物防除剤として使用する場合、農薬製剤上の常法に従い、使用上都合の良い形状に製剤して使用するのが一般的である。即ち、本発明の一般式（Ｉ）で表される縮合複素環化合物又はその塩類は、これらを適当な不活性担体に、また必要に応じて補助剤と一緒に、適当な割合に配合して溶解、分離、懸濁、混合、含浸、吸着させ、適宜の剤形、例えば懸濁剤、乳剤、液剤、水和剤、粒剤、粉剤、錠剤等に製剤して使用すれば良い。本発明で使用できる不活性担体としては固体又は液体の何れであっても良く、固体の担体になりうる材料としては、例えばダイズ粉、穀物粉、木粉、樹皮粉、鋸屑、タバコ茎粉、クルミ粉、ふすま、繊維素粉末、植物エキス抽出後の残査、粉砕合成樹脂等の合成重合体、粘土類（例えばカオリン、ベントナイト、酸性白土等）、タルク類（例えばタルク、ピロフィライド等）、シリカ類（例えば珪藻土、珪砂、雲母、ホワイトカーボン〔含水微粉珪素、含水珪酸ともいわれる合成高分子珪酸で、製品により珪酸カルシウムを主成分として含むものもある。〕）、活性炭、イオウ粉末、軽石、焼成珪藻土、レンガ粉砕物、フライアッシュ、砂、炭酸カルシウム等の無機鉱物性粉末、硫安、燐安、硝安、塩安等の化学肥料、堆肥等を挙げることができ、これらは単独若しくは二種以上の混合物の形で使用される。
【００３４】
液体の担体になりうる材料としては、それ自体溶媒能を有するものの他、溶媒能を有さずとも補助剤の助けにより有効成分を分散させうることとなるものから選択され、例えば代表例として次に挙げる担体を例示できるが、これらは単独若しくは二種以上の混合物の形で使用され、例えば水、アルコール類、（例えばメタノール、エタノール、イソプロパノール、ブタノール、エチレングリコール等）、ケトン類、（例えばアセトン、メチルエチルケトン、メチルイソブチルケトン、ジイソブチルケトン、シクロヘキサノン等）、エーテル類（例えばエチルエーテル、ジオキサン、セロソルブ、ジプロピルエーテル、テトラヒドロフラン等）、脂肪族炭化水素類（例えばケロシン、鉱油等）、芳香族炭化水素類（例えばベンゼン、トルエン、キシレン、ソルベントナフサ、アルキルナフタレン等）、ハロゲン化炭化水素類（例えばジクロロエタン、クロロホルム、四塩化炭素、塩素化ベンゼン等）、エステル類（例えば酢酸エチル、ジイソプピルフタレート、ジブチルフタレート、ジオクチルフタレート等）、アミド類（例えばジメチルホルムアミド、ジエチルホルムアミド、ジメチルアセトアミド等）、ニトリル類（例えばアセトニトリル等）、ジメチルスルホキシド類等を挙げることができる。
他の補助剤としては次に例示する代表的な補助剤を挙げることができ、これらの補助剤は目的に応じて使用され、単独で、ある場合は二種以上の補助剤を併用し、又ある場合には全く補助剤を使用しないことも可能である。
【００３５】
有効成分化合物の乳化、分散、可溶化及び／又は湿潤の目的のために界面活性剤が使用され、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高級脂肪酸エステル、ポリオキシエチレン樹脂酸エステル、ポリオキシエチレンソルビタンモノラウレート、ポリオキシエチレンソルビタンモノオレエート、アルキルアリールスルホン酸塩、ナフタレンスルホン酸縮合物、リグニンスルホン酸塩、高級アルコール硫酸エステル等の界面活性剤を例示することができる。
又、有効成分化合物の分散安定化、粘着及び／又は結合の目的のために、次に例示する補助剤を使用することもでき、例えばカゼイン、ゼラチン、澱粉、メチルセルロース、カルボキシメチルセルロース、アラビアゴム、ポリビニルアルコール、松根油、糠油、ベントナイト、リグニンスルホン酸塩等の補助剤を使用することもできる。
【００３６】
固体製品の流動性改良のために次に挙げる補助剤を使用することもでき、例えばワックス、ステアリン酸塩、燐酸アルキルエステル等の補助剤を使用できる。
懸濁性製品の解こう剤として、例えばナフタレンスルホン酸縮合物、縮合燐酸塩等の補助剤を使用することもできる。
消泡剤としては、例えばシリコーン油等の補助剤を使用することもできる。
有効成分化合物の配合割合は必要に応じて加減することができ、例えば粉剤或いは粒剤とする場合は０．０１〜５０重量％、又乳剤或いは水和剤とする場合も同様０．０１〜５０重量％が適当である。
【００３７】
本発明の一般式（Ｉ）で表される縮合複素環誘導体又はその塩類を有効成分とする有害生物防除剤は、各種害虫を防除するために、そのまま、又は水等で適宜希釈し、若しくは懸濁させた形で害虫防除に有効な量を当該害虫の発生が予測される作物若しくは発生が好ましくない場所に適用して使用すれば良い。本発明の一般式（Ｉ）で表される縮合複素環誘導体又はその塩類を有効成分とする有害生物防除剤の使用量は、種々の因子、例えば目的、対象害虫、作物の生育状況、害虫の発生傾向、天候環境条件、剤型施用方法、施用場所、施用時期等により変動するが、有効成分化合物として１０アール当たり０．０１ｇ〜５ｋｇの範囲から目的に応じて適宜選択すれば良い。
本発明の一般式（Ｉ）で表される縮合複素環誘導体又はその塩類を有効成分とする有害生物防除剤は、更にその防除対象害虫、防除適期の拡大のため、或いは薬量の低減をはかる目的で、他の農園芸用殺虫剤又は殺菌剤と混合して使用することも可能である。
以下に本発明の代表的な実施例及び試験例を示すが、本発明はこれらに限定されるものではない。
尚、処方例中、部とあるのは重量部を示す。
【００３８】
処方例１．
第２表記載の化合物 ５０部
キシレン ４０部
ポリオキシエチレンノニルフェニルエーテルと
アルキルベンゼンスルホン酸カルシウムとの混合物 １０部
以上を均一に混合溶解して乳剤とする。
処方例２．
第２表記載の化合物 ３部
クレー粉末 ８２部
珪藻土粉末 １５部
以上を均一に混合粉砕して粉剤とする。
【００３９】
処方例３．
第２表記載の化合物 ５部
ベントナイトとクレーの混合粉末 ９０部
リグニンスルホン酸カルシウム ５部
以上を均一に混合し、適量の水を加えて混練し、造粒、乾燥して粒剤とする。
処方例４．
第２表記載の化合物 ２０部
カオリンと合成高分散珪酸 ７５部
ポリオキシエチレンノニルフェニルエーテルとアル
キルベンゼンスルホン酸カルシウムとの混合物 ５部
以上を均一に混合粉砕して水和剤とする。
【００４０】
試験例１．モモアカアブラムシ(Myzus Persicae)に対する防除価試験
直径８ｃｍ、高さ８ｃｍのプラスチックポットにハクサイを植えてモモアカアブラムシを繁殖させ、それぞれのポットの寄生虫数を調査した。本発明の一般式（Ｉ）で表される縮合複素環化合物又はその塩類を水に分散させて５００ｐｐｍの薬液とし、該薬液をポット植えハクサイの茎葉に散布して風乾後、ポットを温室に保管し、薬剤散布後６日目にそれぞれのハクサイに寄生しているモモアカアブラムシの寄生虫数を調査し、下記の式より防除価を算出し、下記基準に従って判定を行った。
【００４１】
防除価＝１００−〔（Ｔ×Ｃａ）／（Ｔａ×Ｃ）〕ｘ１００
Ｔａ：処理区の散布前寄生虫数
Ｔ ：処理区の散布後寄生虫数
Ｃａ：無処理区の散布前寄生虫数
Ｃ ：無処理区の散布期間後の寄生虫数
判定基準
Ａ・・・防除価１００％
Ｂ・・・防除価９９％〜９０％
Ｃ・・・防除価８９％〜８０％
Ｄ・・・防除価７９％〜５０％
【００４２】
試験例２．トビイロウンカ（Nilaparvata lugens）に対する殺虫試験
本発明の一般式（Ｉ）で表される縮合複素環誘導体又はその塩類を水に分散させて５００ｐｐｍの薬液に希釈し、該薬液にイネ実生（品種：日本晴）を３０秒間浸漬し、風乾した後にガラス試験管に入れ、トビイロウンカ３令幼虫を各１０頭づつ接種した後に綿栓をし、接種８日後に生死虫数を調査し、死虫率を下記の式より算出し、下記の判定基準に従って判定を行った。
【数１】
【００４３】
結果、本発明の一般式（Ｉ）で示される縮合複素環誘導体を有効成分とする有害生物防除剤で、化合物No. ４、７の化合物はモモアカアブラムシに対してＡ以上の活性を示し、化合物No. ４、７の化合物はトビイロウンカに対してＤ以上の活性を示した。[0001]
BACKGROUND OF THE INVENTION
The present invention relates to a novel fused heterocyclic derivative useful as a pesticidal agent, its use and an intermediate thereof.
[0002]
[Prior art]
JP-A-1-132580, JP-A-2-290871, JP-A-6-234748 and JP-A-8-325239 disclose that triazinone derivatives, imidazole derivatives or quinazoline derivatives are useful as pest control agents. ing.
[0003]
[Problems to be solved by the invention]
As a result of intensive studies to create a novel pest control agent, the present inventors have found that the heterocyclic derivative represented by the general formula (I) of the present invention and an intermediate for producing the compound are generally The compound represented by the formula (II) is a novel compound not yet described in the literature, and the heterocyclic derivative represented by the general formula (I) has an excellent effect on various pests at a low dose. The present invention has been found and the present invention has been completed.
[0004]
[Means for Solving the Problems]
The present invention relates to general formula (I)
[Chemical 3]
[0005]
Phenyl C 1 -C 3 alkyl group, which may be the same or different, halogen atom, C 1 -C 3 alkyl group, halo C 1 -C 3 alkyl group, C 1 -C 3 alkoxy group, halo C 1 -C 3 A phenyl C 1 -C 3 alkyl group, a phenylcarbonyl group, or the same having 1 to 3 substituents selected from an alkoxy group, a C 1 -C 3 alkylthio group or a halo C 1 -C 3 alkylthio group on the ring Or may be different, halogen atom, C 1 -C 3 alkyl group, halo C 1 -C 3 alkyl group, C 1 -C 3 alkoxy group, halo C 1 -C 3 alkoxy group, C 1 -C 3 alkylthio group Or a phenylcarbonyl group having 1 to 3 substituents selected from a halo C 1 -C 3 alkylthio group on the ring.
[0006]
R 1 and R 2 together represent a 5- to 6-membered heterocycle interrupted by 1 to 3 heteroatoms selected from the same or different oxygen, sulfur or nitrogen atoms. , X may be the same or different, and may be a hydrogen atom, a halogen atom, a cyano group, a nitro group, a C 1 -C 3 alkyl group, a halo C 1 -C 3 alkyl group, a C 2 -C 4 alkenyl group, or a halo C 2. -C 4 alkenyl group, C 2 -C 4 alkynyl group, halo C 2 -C 4 alkynyl group, C 1 -C 3 alkoxy group, halo C 1 -C 3 alkoxy groups, C 1 -C 3 alkylthio group, or a halo A substituent selected from C 1 -C 3 alkylthio groups is shown. n represents an integer of 0 to 3.
[0007]
A represents —NH—CH 2 — or —N═CH—, R 3 may be a pyridyl group or an N-oxide group thereof, which may be the same or different, and is a halogen atom, a cyano group, a nitro group, C 1 -C 3 1 selected from an alkyl group, a halo C 1 -C 3 alkyl group, a C 1 -C 3 alkoxy group, a halo C 1 -C 3 alkoxy group, a C 1 -C 3 alkylthio group or a halo C 1 -C 3 alkylthio group A pyridyl group having 3 substituents or an N-oxide group, a thiazole group thereof, which may be the same or different, a halogen atom, a cyano group, a nitro group, a C 1 -C 3 alkyl group, a halo C 1 -C 1-3 substituents selected from 3 alkyl groups, C 1 -C 3 alkoxy groups, halo C 1 -C 3 alkoxy groups, C 1 -C 3 alkylthio groups, or halo C 1 -C 3 alkylthio groups It has a thiazole group. ]
And a pesticide containing the fused heterocyclic derivative as an active ingredient, and an intermediate compound for producing the fused heterocyclic derivative (II)
[0008]
[Formula 4]
It is related with the compound represented by these.
[0009]
The condensed heterocyclic derivative represented by the general formula (I) of the present invention or a salt thereof has tautomers in terms of its chemical structure, and the present invention includes these tautomers. is there. Further, salts of these compounds with inorganic or organic acids are also included.
[0010]
DETAILED DESCRIPTION OF THE INVENTION
In the condensed heterocyclic derivative represented by the general formula (I) of the present invention, in the definition of each substituent, “halogen atom” means chlorine atom, bromine atom, iodine atom or fluorine atom, and “C 1- The “C 3 alkyl group” refers to a linear or branched alkyl group having 1 to 3 carbon atoms, for example, methyl, ethyl, n-propyl, i-propyl and the like. The “halo C 1 -C 3 alkyl group” refers to a linear or branched alkyl group having 1 to 3 carbon atoms, which is substituted with one or more halogen atoms which may be the same or different. “2- C 4 alkenyl group” means a linear or branched alkenyl group having 2 to 4 carbon atoms having one or more double bonds, such as vinyl, allyl, isopropenyl, 1-methylpropenyl. 1-butenyl, 2-butenyl, 3-butenyl, etc., and the “halo C 2 -C 4 alkenyl group” is 2 to 4 carbon atoms substituted with one or more halogen atoms which may be the same or different. A linear or branched alkenyl group. The “C 2 -C 4 alkynyl group” refers to a linear or branched alkynyl group having 2 to 4 carbon atoms having one or more triple bonds, such as ethynyl, 2-propynyl, 1- Methyl-2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl and the like, and “halo C 2 -C 4 alkynyl group” is carbon substituted with one or more halogen atoms which may be the same or different A linear or branched alkynyl group having 2 to 4 atoms,
[0011]
Examples of the “5- to 6-membered heterocycle interrupted by 1 to 3 heteroatoms selected from oxygen atom, sulfur atom or nitrogen atom which may be the same or different” include furan, thiophene, pyrrole, oxazole, A 5- to 6-membered ring such as isoxazole, thiazole, isothiazole, pyrazole, imidazole, 1,2,3-thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine and the like shall be shown.
[0012]
The condensed heterocyclic derivative represented by the general formula (I) of the present invention can be produced through the compound represented by the general formula (II) which is an intermediate, for example, by the production method shown below.
First, the compound represented by the general formula (II), which is an intermediate of the present invention, can be produced, for example, by the production method shown below.
[0013]
Manufacturing method 1.
[Chemical formula 5]
[0014]
A compound represented by the general formula (IX) and a compound represented by the general formula (VIII) are reacted in the presence of an inert solvent and a catalyst to obtain a compound represented by the general formula (VII). VII) is isolated or not isolated and subjected to a reduction reaction to obtain a compound represented by the general formula (VI), and the compound (VI) is isolated or not isolated and subjected to a cyclization reaction, The compound represented by general formula (II) can be produced by carrying out the hydrolysis reaction with or without isolating compound (V) as the compound represented by (V).
This reaction can be produced according to the production method disclosed in JP-A-8-325239.
[0015]
The compound represented by the general formula (IX) which is a starting material for the above reaction is obtained according to a known method. Chem. Soc. , 1045 (1956), J. et al. Chem. Soc. 1372 (1960); Chem. Soc. , 386 (1943), Ber. , 100 , 3664 (1967) and the like.
[0016]
The typical examples of the compound represented by the general formula (II) of the present invention are shown in Table 1 below, but the present invention is not limited to these.
Formula (II)
[Chemical 6]
[Table 1]
[Table 2]
Next, a typical method for producing the condensed heterocyclic derivative represented by the general formula (I) of the present invention or a salt thereof is schematically shown below.
Manufacturing method 2.
[Chemical 7]
[0020]
The condensed heterocyclic derivative represented by the general formula (I-1) is obtained by reacting the compound represented by the general formula (II) obtained by the production method 1 with the compound represented by the general formula (IV). And the condensed heterocyclic derivative (I-1) is further reacted with a halide represented by the general formula (III) to give a condensed heterocyclic derivative represented by the general formula (I-2). Can be manufactured.
Further, the condensed heterocyclic derivative represented by the general formula (I-3) can be produced by reducing the condensed heterocyclic derivative represented by the general formula (I-1).
This reaction can be produced according to the production method disclosed in JP-A-8-325239.
[0021]
In the following, typical examples of the condensed heterocyclic derivatives represented by the general formula (I) of the present invention or salts thereof are illustrated in Table 2, but the present invention is not limited to these.
Formula (I)
[Chemical 8]
[Table 3]
[Table 4]
【Example】
Typical examples of the present invention are shown below, but the present invention is not limited thereto.
Example 1. Preparation of 3,4-dihydro-3- (pyridylmethylideneamino) -pyrido [2,3-d] pyrimidin-2-one
1-1. Preparation of t-butyl 2- (2-aminopyridyl-3-methylidene) carbazic acid 2.30 g (18.8 mmol) 2-aminopyridine-3-aldehyde and 2.48 g (18.8 mmol) t- Butylcarbazic acid and 1 drop of acetic acid were added to 20 ml of methanol, and the reaction was carried out with heating under reflux for 5 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, and the precipitated crystals were collected by filtration to obtain 4 g of the desired product.
1 H-NMR [CDCl 3 / TMS, δ value (ppm)]
1.45 (s, 9H), 6.60 (dd, 1H), 7.4 (brs, 2H), 7.45 (dd, 1H), 7.95 (dd, 1H), 8.00 (brs, 1H), 11.0 (brs, 1H)
Yield: 90%
[0026]
1-2. Preparation of t-butyl 2- (2-aminopyridyl-3-methyl) carbazic acid 2 g (8.5 mmol) of t-butyl 2- (2-aminopyridyl-3-methylidene) carbazic acid obtained in 1-1 And 0.2 g of 5% palladium carbon were added to 20 ml of acetic acid, and catalytic reduction was performed at 4 to 5 kg / m 2 . After hydrogen absorption stopped, the catalyst was removed by filtration, and the solvent was distilled off under reduced pressure to obtain 2.0 g of the desired product.
1 H-NMR [CDCl 3 / TMS, δ value (ppm)]
1.46 (s, 9H), 3.95 (d, 2H), 4.05 (brs, 1H), 5.35 (brs, 2H), 6.10 (brs, 1H), 6.60 (dd, 1H), 7.30 (dd, 1H), 8.02 (dd, 1H)
Yield: Quantitative
1-3. Preparation of 3,4-dihydro-3- (t-butoxycarbonylamino) -pyrido [2,3-d] pyrimidin-2-one.
2 g (8.5 mmol) of t-butyl 2- (2-aminopyridyl-3-methyl) carbazic acid obtained in 1-2 and 1.38 g (8.5 mmol) of 1,1′-carbonylbis- 1H-imidazole (CDI) was dissolved in 20 ml of dry tetrahydrofuran, and the reaction was carried out with heating under reflux for 5 hours. After completion of the reaction, the reaction solution was poured into 30 ml of water, and the target product was extracted with 30 ml of chloroform three times. The combined extracts were washed with saturated brine and dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure, and the residue was crystallized from ethyl acetate to obtain 0.8 g of the desired product.
1 H-NMR [CDCl 3 / TMS, δ value (ppm)]
1.50 (s, 9H), 4.76 (S, 1H), 6.78 (brs, 1H), 6.98 (dd, 1H), 7.37 (d, 1H), 8.21 (d, 1H), 8.75 (brs, 1H)
Yield: 35%
[0028]
1-4. Preparation of 3,4-dihydro-3-amino-pyrido [2,3-d] pyrimidin-2-one 3,4-dihydro-3- (t-butoxycarbonylamino) -pyrido obtained in 1-3 [ 2,3-d] pyrimidin-2-one (0.8 g, 3 mmol) was added to 5 ml of trifluoroacetic acid at 0 ° C., followed by reaction at room temperature for 1 hour. After completion of the reaction, the solvent was distilled off under reduced pressure, and the residue was recrystallized from ethanol to obtain 0.35 g of the desired product.
1 H-NMR [CDCl 3 / TMS, δ value (ppm)]
4.0 ~ 4.5 (brS, 2H), 4.57 (s, 1H), 6.99 (dd, 1H), 7.64 (d, 1H), 8.13 (d, 1H)
10.34 (brs, 1H)
Yield: 71%
[0029]
1-5. Preparation of 3,4-dihydro-3- (pyridylmethylideneamino) -pyrido [2,3-d] pyrimidin-2-one 3,4-dihydro-3-amino-pyrido [2 obtained in 1-4 , 3-d] pyrimidin-2-one 0.3 g (1.8 mmol) and 0.2 g (1.8 mmol) of nicotinic aldehyde and 1 drop of sulfuric acid were added to 10 ml of methanol and heated under reflux for 3 hours. To react. After completion of the reaction, the reaction solution was cooled to room temperature, and the precipitated crystals were collected by filtration to obtain 0.35 g of the desired product.
Physical properties: m. p. 253.2-255.0 ° C
1 H-NMR [DMSO-d 6 / TMS, δ value (ppm)]
2.50 (S, 3H), 4.95 (s, 2H), 7.5 (dd, 1H), 8.11 (S, 1H), 8.16 (m, 1H), 8.39 (s, 1H), 8.62 (m, 1H), 8.90 (d, 1H), 10.75 (brs, 1H)
Yield: 76%
[0030]
The pest control agent containing the condensed heterocyclic derivative represented by the general formula (I) of the present invention as an active ingredient is various agricultural and forestry, horticulture, stored grain pests and hygiene that harm rice plants, vegetables, fruit trees, other crops, and florets. Suitable for controlling pests such as pests and nematodes. Dialeurodes citri, Bemicia tabaci, Trialeurodes vaporariorum, Brevicoryne brassicae, Aphis gossipii, Rhopalosiphum padi, ero C cerciferus), citrus scale insect (Pulvinaria aurantii), mandarin orange Le scale insects (Pseudaonidia duplex), pear Mar scale insects (Comstockaspis perniciosa), Unaspis yanonensis (Unaspis yanonensis), Hemiptera etc.,
[0031]
Sperm nematode (Pratylenchus coffeae), potato cyst nematode (Globodera rostochiensis), root-knot nematode (Meloidogyne sp.) It also has an insecticidal effect against nematodes. Scientific names are based on the 1987 Agricultural and Forestry Animal and Insect Directory (Japan Society for Applied Animal Entomology).
[0032]
The pest control agent containing the condensed heterocyclic derivative represented by the general formula (I) of the present invention or a salt thereof as an active ingredient is the above-mentioned pest or sanitary pest that harms paddy rice, vegetables, fruit trees, other crops, flowers, etc. Therefore, rice plants, fruit trees, vegetables and other crops, and florets before the occurrence of the pests or when the occurrence of the pests is confirmed are matched with the time when the occurrence of the pests is predicted. In the case of paddy field water, foliage, soil, etc. and sanitary pests, the desired effect of the insecticide of the present invention can be achieved by treating it in a house that harms human livestock, a groove around the house, etc. However, the present invention is not limited to only these embodiments.
[0033]
When the condensed heterocyclic derivative represented by the general formula (I) of the present invention or a salt thereof is used as a pest control agent, it should be formulated into a convenient form according to the conventional method for agricultural chemical preparations. Is common. That is, the condensed heterocyclic compound represented by the general formula (I) of the present invention or a salt thereof is blended in an appropriate ratio together with an appropriate inert carrier and, if necessary, an auxiliary agent. It may be dissolved, separated, suspended, mixed, impregnated, adsorbed and formulated into an appropriate dosage form such as a suspension, emulsion, liquid, wettable powder, granule, powder, tablet and the like. The inert carrier that can be used in the present invention may be either solid or liquid. Examples of materials that can be used as a solid carrier include soybean flour, cereal flour, wood flour, bark flour, sawdust, tobacco stem flour, Walnut powder, bran, fiber powder, residue after extraction of plant extract, synthetic polymer such as pulverized synthetic resin, clays (eg kaolin, bentonite, acid clay), talc (eg talc, pyrophyllide etc.), silica (E.g., diatomaceous earth, silica sand, mica, white carbon [some synthetic polymeric silicic acid, also called hydrous fine silicon, hydrous silicic acid, and some products contain calcium silicate as the main component]), activated carbon, sulfur powder, pumice, calcined Examples include inorganic mineral powders such as diatomaceous earth, brick ground, fly ash, sand, calcium carbonate, chemical fertilizers such as ammonium sulfate, phosphate, nitrate, and salt, compost, etc. Come, it is used in the form of singly or a mixture of two or more.
[0034]
The material that can be used as a liquid carrier is selected from those having solvent ability itself and those having no solvent ability and capable of dispersing active ingredients with the aid of adjuvants. Examples of the carriers listed above are used alone or in the form of a mixture of two or more thereof, for example, water, alcohols (for example, methanol, ethanol, isopropanol, butanol, ethylene glycol, etc.), ketones (for example, acetone). , Methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, etc.), ethers (eg, ethyl ether, dioxane, cellosolve, dipropyl ether, tetrahydrofuran, etc.), aliphatic hydrocarbons (eg, kerosene, mineral oil, etc.), aromatic hydrocarbons (E.g. benzene, toluene, Silene, solvent naphtha, alkylnaphthalene, etc.), halogenated hydrocarbons (eg, dichloroethane, chloroform, carbon tetrachloride, chlorinated benzene, etc.), esters (eg, ethyl acetate, diisopropylpropyl phthalate, dibutyl phthalate, dioctyl phthalate, etc.) Amides (for example, dimethylformamide, diethylformamide, dimethylacetamide, etc.), nitriles (for example, acetonitrile, etc.), dimethylsulfoxides, and the like.
As other adjuvants, the following typical adjuvants can be mentioned, and these adjuvants are used depending on the purpose and are used alone, or in some cases, two or more kinds of adjuvants are used together. In some cases it is possible to use no adjuvants at all.
[0035]
Surfactants are used for the purpose of emulsifying, dispersing, solubilizing and / or wetting of the active ingredient compound, such as polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene higher fatty acid ester, polyoxyethylene. Examples of surfactants such as resin acid ester, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monooleate, alkylaryl sulfonate, naphthalene sulfonate condensate, lignin sulfonate, higher alcohol sulfate Can do.
In addition, for the purpose of stabilizing the dispersion of the active ingredient compound, adhesion and / or binding, the following auxiliary agents can be used, for example, casein, gelatin, starch, methylcellulose, carboxymethylcellulose, gum arabic, polyvinyl Adjuvants such as alcohol, pine oil, coconut oil, bentonite and lignin sulfonate can also be used.
[0036]
In order to improve the fluidity of the solid product, the following adjuvants can also be used, and for example, adjuvants such as waxes, stearates and alkyl phosphates can be used.
As a peptizer for a suspension product, for example, auxiliary agents such as naphthalenesulfonic acid condensate and condensed phosphate can be used.
As the antifoaming agent, for example, an auxiliary agent such as silicone oil can be used.
The blending ratio of the active ingredient compound can be adjusted as necessary. For example, 0.01 to 50% by weight in the case of powder or granule, and 0.01 to 50 in the case of emulsion or wettable powder. Weight percent is appropriate.
[0037]
The pest control agent comprising the condensed heterocyclic derivative represented by the general formula (I) or a salt thereof of the present invention as an active ingredient is diluted as it is or appropriately with water or the like in order to control various pests. An amount effective for pest control in a turbid form may be applied to a crop where the occurrence of the pest is predicted or a place where the occurrence is undesirable. The amount of the pest control agent comprising the fused heterocyclic derivative represented by the general formula (I) of the present invention or a salt thereof as an active ingredient is various factors such as the purpose, the target pest, the growth status of the crop, the pest Although it varies depending on the occurrence tendency, weather environment conditions, dosage form application method, application location, application time, etc., the active ingredient compound may be appropriately selected from the range of 0.01 g to 5 kg per 10 ares according to the purpose.
The pest control agent comprising the fused heterocyclic derivative represented by the general formula (I) of the present invention or a salt thereof as an active ingredient is intended to further increase the control target pest, the control period, or reduce the dose. For the purpose, it can also be used by mixing with other agricultural or horticultural insecticides or fungicides.
Although the typical Example and test example of this invention are shown below, this invention is not limited to these.
In the prescription examples, “parts” means “parts by weight”.
[0038]
Formulation Example 1
Compounds listed in Table 2 50 parts Xylene 40 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate 10 parts or more is mixed and dissolved uniformly to prepare an emulsion.
Formulation Example 2
Compounds listed in Table 2 3 parts clay powder 82 parts diatomaceous earth powder 15 parts or more are mixed and ground uniformly to form a powder.
[0039]
Formulation Example 3
Compound shown in Table 2 5 parts Bentonite and clay mixed powder 90 parts lignin sulfonate 5 parts or more is uniformly mixed, kneaded with an appropriate amount of water, granulated and dried to form granules.
Formulation Example 4
Compounds listed in Table 2 20 parts Kaolin, synthetic highly dispersed silicic acid 75 parts Polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate 5 parts or more are uniformly mixed and ground to obtain a wettable powder.
[0040]
Test Example 1 Test for control of peach aphid (Myzus Persicae) Chinese cabbage was planted in plastic pots having a diameter of 8 cm and a height of 8 cm to breed peach mosquito aphids, and the number of parasites in each pot was investigated. The condensed heterocyclic compound represented by the general formula (I) of the present invention or a salt thereof is dispersed in water to give a chemical solution of 500 ppm. The chemical solution is sprayed on the stems and leaves of potted Chinese cabbage and air-dried, and the pot is stored in a greenhouse. Then, on the 6th day after the spraying of the drug, the number of parasites of the peach aphid parasitic on each Chinese cabbage was investigated, the control value was calculated from the following formula, and the determination was made according to the following criteria.
[0041]
Control value = 100 − [(T × Ca) / (Ta × C)] × 100
Ta: Number of parasites before spraying in the treated zone T: Number of parasites after spraying in the treated zone Ca: Number of parasites before spraying in the untreated zone C: Parasitic number judgment criteria A after spraying period in the untreated zone Control value 100%
B ... Control value 99% ~ 90%
C ... Control value 89% -80%
D ... Control value 79% -50%
[0042]
Test Example 2 Insecticidal test against green planthopper (Nilaparvata lugens) The condensed heterocyclic derivative represented by the general formula (I) of the present invention or a salt thereof is dispersed in water and diluted to a chemical solution of 500 ppm, and rice seedlings (variety: Nipponbare) are added to the chemical solution. Was soaked for 30 seconds, air-dried, put into a glass test tube, inoculated with 10 each of the 3rd instar plant larvae, and then plugged with cotton. After 8 days of inoculation, the number of live and dead insects was investigated. And was determined according to the following criteria.
[Expression 1]
[0043]
As a result, the pest control agent comprising the fused heterocyclic derivative represented by the general formula (I) of the present invention as an active ingredient, the compounds Nos. 4 and 7 exhibit A or more activity against peach aphid, Compounds Nos. 4 and 7 showed an activity higher than D against the brown planthopper.
Claims (5)
Ａは-NH-CH2-又は-N=CH-を示し、Ｒ3 はピリジル基又はそのＮ−オキシド基、同一又は異なっても良く、ハロゲン原子、シアノ基、ニトロ基、C1-C3 アルキル基、ハロC1-C3 アルキル基、C1-C3 アルコキシ基、ハロC1-C3 アルコキシ基、C1-C3 アルキルチオ基、又はハロC1-C3 アルキルチオ基から選択される１〜３個の置換基を有するピリジル基又はそのＮ−オキシド基、チアゾール基、又は同一若しくは異なっても良く、ハロゲン原子、シアノ基、ニトロ基、C1-C3 アルキル基、ハロC1-C3 アルキル基、C1-C3 アルコキシ基、ハロC1-C3 アルコキシ基、C1-C3 アルキルチオ基、又はハロC1-C3 アルキルチオ基から選択される１〜２個の置換基を有するチアゾール基を示す。〕
で表される縮合複素環誘導体又はその塩類。Formula (I)
A represents —NH—CH 2 — or —N═CH—, R 3 may be a pyridyl group or an N-oxide group thereof, which may be the same or different, and is a halogen atom, a cyano group, a nitro group, C 1 -C 3 Selected from alkyl groups, halo C 1 -C 3 alkyl groups, C 1 -C 3 alkoxy groups, halo C 1 -C 3 alkoxy groups, C 1 -C 3 alkylthio groups, or halo C 1 -C 3 alkylthio groups A pyridyl group having 1 to 3 substituents or an N-oxide group thereof, a thiazole group, or the same or different, a halogen atom, a cyano group, a nitro group, a C 1 -C 3 alkyl group, a halo C 1- C 3 alkyl group, C 1 -C 3 alkoxy group, halo C 1 -C 3 alkoxy groups, C 1 -C 3 alkylthio group, or a halo C 1 -C 3 1 to 2 substituents selected from alkylthio groups Represents a thiazole group having ]
A condensed heterocyclic derivative represented by the formula:
Ｒ1 及びＲ2 はお互いに一緒になって、同一又は異なっても良い酸素原子、硫黄原子又は窒素原子から選択される１〜３個のヘテロ原子により中断された５〜６員複素環を示し、Ｘは同一又は異なっても良く、水素原子、ハロゲン原子、シアノ基、ニトロ基、C1-C3 アルキル基、ハロC1-C3 アルキル基、 C2-C4アルケニル基、ハロC2-C4 アルケニル基、 C2-C4アルキニル基、ハロC2-C4 アルキニル基、C1-C3 アルコキシ基、ハロC1-C3 アルコキシ基、C1-C3 アルキルチオ基、又はハロC1-C3 アルキルチオ基から選択される置換基を示す。ｎは０〜３の整数を示す。〕
で表される化合物。Formula (II)
R 1 and R 2 together represent a 5- to 6-membered heterocycle interrupted by 1 to 3 heteroatoms selected from the same or different oxygen, sulfur or nitrogen atoms. , X may be the same or different, and may be a hydrogen atom, a halogen atom, a cyano group, a nitro group, a C 1 -C 3 alkyl group, a halo C 1 -C 3 alkyl group, a C 2 -C 4 alkenyl group, or a halo C 2. -C 4 alkenyl group, C 2 -C 4 alkynyl group, halo C 2 -C 4 alkynyl group, C 1 -C 3 alkoxy group, halo C 1 -C 3 alkoxy groups, C 1 -C 3 alkylthio group, or a halo A substituent selected from C 1 -C 3 alkylthio groups is shown. n represents an integer of 0 to 3. ]
A compound represented by
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| CN102876669A (en) * | 2012-10-18 | 2013-01-16 | 广东省昆虫研究所 | Diaphorina citri specific molecular marker DNA (deoxyribonucleic acid) sequence and identification primer and identification method thereof |
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| ES2310039T3 (en) | 1998-05-26 | 2008-12-16 | Warner-Lambert Company Llc | BICYCLE PYRIMIDINES AND BICYCLE 3,4-DIHYDROPIRIMIDINS AS INHIBITORS OF CELL PROLIFERATION. |
| US8034931B2 (en) | 2003-05-12 | 2011-10-11 | Nihon Nohyaku Co., Ltd. | Process for producing substituted aminoquinazolinone derivative, intermediate therefor, and pest control agent |
| JP2005029568A (en) * | 2003-06-18 | 2005-02-03 | Nippon Nohyaku Co Ltd | Substituted iminoquinazolinone derivative or its salt, noxious organism control agent, and control method |
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| CN102876669A (en) * | 2012-10-18 | 2013-01-16 | 广东省昆虫研究所 | Diaphorina citri specific molecular marker DNA (deoxyribonucleic acid) sequence and identification primer and identification method thereof |
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