JP4796594B2 - 殺虫、殺ダニ、及び殺菌ニトロメチレン化合物 - Google Patents
殺虫、殺ダニ、及び殺菌ニトロメチレン化合物 Download PDFInfo
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- JP4796594B2 JP4796594B2 JP2007558294A JP2007558294A JP4796594B2 JP 4796594 B2 JP4796594 B2 JP 4796594B2 JP 2007558294 A JP2007558294 A JP 2007558294A JP 2007558294 A JP2007558294 A JP 2007558294A JP 4796594 B2 JP4796594 B2 JP 4796594B2
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
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Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen
- A01N35/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen containing a carbon-to-nitrogen double bond
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
- A01N43/38—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings condensed with carbocyclic rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
- C07C251/74—Hydrazones having doubly-bound carbon atoms of hydrazone groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C251/76—Hydrazones having doubly-bound carbon atoms of hydrazone groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of a saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/76—Nitrogen atoms to which a second hetero atom is attached
- C07D213/77—Hydrazine radicals
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- Plural Heterocyclic Compounds (AREA)
Description
(式中、
Xは、a)フェニル、低級フェニルアルコキシ、フェノキシ、又はベンジルであるか、又はb)群a)の1つの置換基及びC1〜C4アルコキシ、ハロゲン、低級アルキル及び低級アルキルチオから選択される1つ又は複数の置換基であるか、又はc)フェニルに結合してフェニルと一緒になってジベンゾフラニル等の複数結合複素環を形成し、
Yは、H、C1〜C4アルカノイル、C1〜C4ハロアルカノイル、ジアルコキシホスホリル、アルキルアミノカルボニル、ハロアルキルスルホニル、又はC1〜C4アルコキシカルボニルであり、
Rは、H、C1〜C6アルキル、C1〜C6アルコキシ、C3〜C6シクロアルコキシ、ハロアルキル、アルコキシアルキル、アリールアルコキシ、アルケニル、アルキルチオ、アルコキシカルボニル、アルキルアミノ、ヘテロアリール、アリールアルキル、ハロアルコキシ、アリールオキシ、又はC3〜C6シクロアルキルであり、
ZはO又はSである)を有する化合物を開示している。
(式中、Rは、C1〜C6アルコキシ又はC1〜C6アルキルであり、R1は、非置換若しくはC1〜C4アルコキシ、C1〜C4アルキル、C1〜C4アルキルチオ、ハロゲン、C1〜C4ハロアルキル及びニトロから選択される1つ又は複数の置換基で置換されたフルオレニル、チエニル、ピリジル又はチアゾリルであり、R2は、C1〜C6アルキル、C3〜C6シクロアルキル、C1〜C6ハロアルキル、C2〜C6アルケニル、又はC2〜C6アルコキシアルキルである)を有する化合物を開示している。この化合物は、ダニ及び線虫を駆除するのに有効である。
(式中、Rは、水素又はCO2CH(CH3)2である)を有する化合物、この調製方法、及びビフェナゼートの調製方法を開示している。
(式中、Xは、フェニル、フェニルアルコキシ、フェノキシ、又はベンジル単独、或いは1つ又は複数のハロゲン、アルキル、又はアルキルチオとの組合せであり、Yは、水素、アルカノイル、ハロアルカノイル、又はアルコキシカルボニルであり、Rは、水素、アルキル、ハロアルキル、アルコキシ、ハロアルコキシ、又はフェニルアルコキシである)のフェニルヒドラジン誘導体化合物を使用する菌類の駆除方法を開示している。
(式中、R1はアルキルであり、R2及びR3は独立に選択されたアリール基である)を有する化合物を開示している。また、この化合物を中間体として使用するビフェナゼートの製造方法も開示している。
(式中、R1及びR2は明細書で定義されている通りである)である。また、この化合物及び中間体は、藻菌類が原因の農作物の病気を予防及び治癒することができ、また、胡瓜のべと病に有効であることが開示されている。
(式中、R1は、ハロゲン原子又は好ましくは1〜4個の炭素原子を含むアルキル基、−NO2又は好ましくは1〜4個の炭素原子を含むアルコキシ基又はクロロフェノキシ基又はCF3基で置換されていてもよいフェニル基を表し、R2は、1〜4個の炭素原子を含むアルキル基又はR1と同じ方法で置換されていてもよいフェニル基を表す)のニトラゾン又はその様なニトラゾンの塩を担体と一緒に含む、害虫を駆除するための製剤を開示している。
本発明は、式:
(式中、
R1は、非置換若しくは置換ビフェニル、又は非置換若しくは置換フルオレン、若しくはカルバゾール環、又は非置換若しくは置換ピリジン環であり、
R2は、水素又はアルキルである)
を有する化合物に関する。
(式中、
R1は、非置換及び置換ビフェニル部分、非置換及び置換フルオレニル部分、非置換及び置換カルバゾリル部分、並びに非置換及び置換ピリジル部分からなる群から選択され、
R2は、水素又はアルキルである)の化合物を含む物質の組成物に関する。
(A)式:
(式中、
R1は、非置換及び置換ビフェニル部分、非置換及び置換フルオレニル部分、非置換及び置換カルバゾリル部分、並びに非置換及び置換ピリジル部分からなる群から選択され、
R2は、水素又はアルキルである)の化合物の殺虫有効量、及び
(B)許容し得る担体、
を含む殺虫組成物に関する。
(式中、
R1は、非置換及び置換ビフェニル部分、非置換及び置換フルオレニル部分、非置換及び置換カルバゾリル部分、並びに非置換及び置換ピリジル部分からなる群から選択され、
R2は、水素又はアルキルである)の化合物の殺虫有効量を保護される場所に適用することを含む望ましくない害虫を駆除する方法に関する。
(式中、
R1は、非置換若しくはC1〜C4アルキル、C1〜C6アルコキシで一置換されたビフェニルであり、又はR1は、非置換若しくはC1〜C4アルキルで一置換されたフルオレン又はカルバゾール環であり、又はR1は、非置換若しくはハロゲンで一置換されたピリジン環であり、
R2は、水素又はC1〜C6アルキル若しくは分岐アルキルである)
を有する。
上で言及した通り、本発明の化合物の構造式におけるR1はビフェニル、フルオレニル、カルバゾリル、又はピリジルとすることができ、それぞれは、非置換とすることも又は置換とすることもできる。置換された場合は、一置換が好ましい。
(プロパナール、1−ニトロ、(4−メトキシ−[1,1′−ビフェニル]−3−イル)ヒドラゾンの調製)
370mLの水における20.0gの5−フェニル−o−アニシジンの懸濁液に、30mLの濃塩酸を添加し、混合物を20分間撹拌した。混合物を−5℃まで冷却し、次いで、50mLの水における7.25gの亜硝酸ナトリウムの溶液を、−3〜0℃の温度を維持しながらゆっくりと添加した。混合物を0℃で30分間撹拌し、次いで、82gの酢酸ナトリウムを添加して510mLの酢酸ジアゾニウムの溶液を得た。この溶液(125mL)を、40mLのエタノール及び10mLの水における2.23gの1−ニトロプロパン及び1.0gの水酸化ナトリウムの氷冷溶液に素早く添加した。この混合物を室温まで温め、16時間撹拌した。得られた赤色固体をろ過し、水で洗浄して5.7gの生成物を得、その構造を1H NMRで確認した。DMSOにおける化合物のNMRデータ(ppm)は、s(1)12.5、d(1)7.8;m(7)7.5〜7.0;s(3)3.9;q(2)2.8;t(3)1.2であり、その構造は:
であった。
DMSOにおける化合物のNMRデータ(ppm)は、s(1)12.5;d(1)7.8;m(7)7.7〜6.8;s(3)3.9;t(1)3.8;t(1)2.7;m(2)1.7;m(3)1.0であり、その構造は;
であった。
(貯蔵溶液の調製)
次の例において、本発明の化合物のための貯蔵溶液を、8mLのアセトンに0.24gの各テスト化合物を溶解し、72mLの蒸留水+3滴のエトキシ化ソルビタンモノラウレート、即ち湿潤剤を添加して3000ppmで調製した。この貯蔵溶液を、本発明の代表的化合物の殺虫使用を証明するために使用した。以後の各例に対しては、この貯蔵溶液を使用し、特定の希釈を行った。本発明の化合物での処理が含まれる以下で検討される全てのテストは、活性化合物が与えられていない対照群を常に伴って繰返すことで、対照群に対する割合(駆除パーセント)に基づく比較を可能にした。
(ダニの殺成虫剤及びダニの殺卵剤テスト)
テスト溶液でのカウピーの主要な葉の処理の1日前に、タングルフットの木を「8の字」の形状に、鉢植えの2つの植物の各1枚である2枚のカウピーの主要な葉のそれぞれに塗布した。茎に近い範囲をダニの殺卵剤テストのために指定し、茎から更に離れた範囲をダニの殺成虫剤テストのために指定した。
(タバコ青虫テスト)
テストされる各化合物のために、上述の通りに調製された貯蔵溶液0.2mLを、5個のダイエット細胞のそれぞれの表面にピペットで載せ、表面全体に拡げ、2時間空気乾燥した。次いで、二齢のヘリコベルパ・ビレセンス(Helicoverpa virescens)幼生を各細胞に導入した。14日後に、生きている幼生の数を各処理及び対照パーセントに対して決定し、アボット(Abbott)式で補正し、計算した。
Claims (4)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US11/072,575 US7592374B2 (en) | 2005-03-03 | 2005-03-03 | Insecticidal nitromethylene compounds |
US11/072,575 | 2005-03-03 | ||
PCT/US2006/007755 WO2006094240A1 (en) | 2005-03-03 | 2006-03-02 | Insecticidal, acaricidal, and fungicidal nitomethylene compounds |
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JP2008537541A JP2008537541A (ja) | 2008-09-18 |
JP4796594B2 true JP4796594B2 (ja) | 2011-10-19 |
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US (1) | US7592374B2 (ja) |
JP (1) | JP4796594B2 (ja) |
GB (1) | GB2437224B (ja) |
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US7511029B2 (en) * | 2007-05-16 | 2009-03-31 | Chemtura Corporation | Pesticidal diazene oxide carboxylates |
CN105028441B (zh) * | 2015-02-12 | 2017-06-09 | 四川利尔作物科学有限公司 | 杀虫杀螨组合物及其应用 |
CN110627692B (zh) * | 2019-10-14 | 2021-09-24 | 河南科技大学 | 丹皮酚苯磺酰腙及其衍生物和其制备方法、植物源杀虫剂及其应用 |
Citations (1)
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JPH07502267A (ja) * | 1991-11-22 | 1995-03-09 | ユニロイヤル ケミカル カンパニー インコーポレイテッド | 殺虫作用のあるフェニルヒドラジン誘導体 |
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US2548480A (en) * | 1951-04-10 | Fungicidal compositions containing | ||
US2547724A (en) * | 1949-12-08 | 1951-04-03 | Us Rubber Co | 2-alkyliminonaphtho [2,3]-1, 3-dithole-4, 9-dione alkohalide and fungicidal compositis containing same |
CH485402A (de) | 1966-06-07 | 1970-02-15 | Ciba Geigy | Schädlingsbekämpfungsmittel |
FR1536991A (fr) * | 1966-06-07 | 1968-08-23 | Ciba Geigy | Nouveaux agents pesticides |
CH570367A5 (ja) | 1967-09-26 | 1975-12-15 | Bayer Ag | |
US3641098A (en) * | 1967-09-26 | 1972-02-08 | Bayer Ag | Cyano substituted phenylhydrazones of 1 2-dicarbonyl compounds |
US3789131A (en) * | 1972-08-03 | 1974-01-29 | Oak Industries Inc | Selective coding system for subscription television |
IT1101444B (it) * | 1978-11-29 | 1985-09-28 | Montedison Spa | Arilidrazo-aldossime e derivati ad attivita' fungicida |
CA1177851A (en) | 1980-07-02 | 1984-11-13 | Nicola Troiani | Fungicidally active arylhydrazoaldoximes and derivatives thereof |
DE3267258D1 (en) | 1981-06-15 | 1985-12-12 | Shell Int Research | 7-substituted 2,3-dihydrobenzofurans, their preparation and their use as pesticides or as chemical intermediates |
US4725302A (en) * | 1984-11-27 | 1988-02-16 | Ciba-Geigy Corporation | Substituted phenylhydrazines and phenyloxadiazolinones and pesticidal usage thereof |
CN1035660A (zh) | 1988-03-10 | 1989-09-20 | 化学工业部沈阳化工研究院 | 2,6-二甲基苯肼衍生物的制备及其应用 |
RU2109730C1 (ru) * | 1991-11-22 | 1998-04-27 | Юнироял Кемикал Компани, Инк. | Фенилгидразиновые производные, способ борьбы с вредителями и инсектоакарицидонематоцидная композиция |
US5567723A (en) * | 1995-07-05 | 1996-10-22 | Uniroyal Chemical Company, Inc. | Miticidal hydrazine compounds and their intermediates |
US6297275B1 (en) * | 1999-09-07 | 2001-10-02 | Uniroyal Chemical Company, Inc. | Method for controlling fungi using phenylhydrazine derivatives |
US6093843A (en) * | 1999-10-06 | 2000-07-25 | Uniroyal Chemical Company, Inc. | 4-hydroxybiphenyl hydrazide derivatives |
US6706895B1 (en) * | 2002-11-14 | 2004-03-16 | Uniroyal Chemical Company, Inc. | 4-methoxybiphenyl hydrazone derivatives |
CA2535986A1 (en) * | 2003-06-24 | 2005-01-20 | Uniroyal Chemical Company, Inc. | Fungicidal phenoxyphenylhydrazine derivatives |
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2005
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2006
- 2006-03-02 GB GB0715424A patent/GB2437224B/en not_active Expired - Fee Related
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JPH07502267A (ja) * | 1991-11-22 | 1995-03-09 | ユニロイヤル ケミカル カンパニー インコーポレイテッド | 殺虫作用のあるフェニルヒドラジン誘導体 |
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US7592374B2 (en) | 2009-09-22 |
US20060199850A1 (en) | 2006-09-07 |
GB0715424D0 (en) | 2007-09-19 |
WO2006094240A1 (en) | 2006-09-08 |
JP2008537541A (ja) | 2008-09-18 |
GB2437224B (en) | 2009-09-23 |
GB2437224A (en) | 2007-10-17 |
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