JP2000502095A - 新規な5―アミノ―3―シアノ―4―エチルスルフィニル―1―フェニル―ピラゾール化合物及びその農薬としての使用 - Google Patents
新規な5―アミノ―3―シアノ―4―エチルスルフィニル―1―フェニル―ピラゾール化合物及びその農薬としての使用Info
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- JP2000502095A JP2000502095A JP9522508A JP52250897A JP2000502095A JP 2000502095 A JP2000502095 A JP 2000502095A JP 9522508 A JP9522508 A JP 9522508A JP 52250897 A JP52250897 A JP 52250897A JP 2000502095 A JP2000502095 A JP 2000502095A
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- cyano
- dichloro
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D231/18—One oxygen or sulfur atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D231/38—Nitrogen atoms
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- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.式(I): 〔式中、Xは塩素または臭素、Yはトリフルオロメチルまたはトリフルオロメト キシ、R1は水素、メチルまたはエチルを表す〕の化合物。 2.Xが塩素、Yがトリフルオロメチルを表す請求項1に記載の化合物。 3.R1が水素またはメチルを表す請求項1または2に記載の化合物。 4.5−アミノ−3−シアノ−1−(2,6−ジクロロ−4−トリフルオロメチ ルフェニル)−4−エチルスルフィニルピラゾール: 5−アミノ−3−シアノ−1−(2,6−ジクロロ−4−ト リフルオロメトキシフェニル)−4−エチルスルフィニルピラゾール; 5−アミノ−1−(2−ブロモ−6−クロロ−4−トリフルオロメチルフェニ ル)−4−エチルスルフィニルピラゾール; 5−アミノ−1−(2−ブロモ−6−クロロ−4−トリフルオロメトキシフェ ニル)−4−エチルスルフィニルピラゾール: 3−シアノ−1−(2,6−ジクロロ−4−トリフルオロメチルフェニル)− 4−エチルスルフィニル−5−メチルアミノピラゾール; 3−シアノ−1−(2,6−ジクロロ−4−トリフルオロメチルフェニル)− 4−エチルスルフィニル−5−エチルアミノピラゾール;または 1−(2−ブロモ−6−クロロ−4−トリフルオロメトキシフェニル)−4− エチルスルフィニル−5−エチルアミノピラゾール、 であることを特徴とする請求項1から3のいずれか一項に記載の化合物。 5.5−アミノ−3−シアノ−1−(2,6−ジクロロ−4− トリフルオロメチルフェニル)−4−エチルスルフィニルピラゾール。 6.3−シアノ−1−(2,6−ジクロロ−4−トリフルオロメチルフェニル) −4−エチルスルフィニル−5−メチルアミノピラゾール。 7.有効成分として請求項1から6のいずれか一項に記載の化合物を有効量で含 み、同時に、農薬として許容される担体及び農薬として許容される界面活性剤の グループから選択される少なくとも1つの成分を含む農薬組成物。 8.請求項1から6のいずれか一項に記載の化合物を有効量で所定の場所に施用 することを特徴とする該場所の有害生物の防除方法。 9.式(I)の化合物の施用量が1ヘクタールあたり約5g〜約1000gであ ることを特徴とする請求項8に記載の方法。 10.前記場所が作物栽培に使用中の地区または使用予定の地区であることを特 徴とする請求項8または9に記載の方法。 11.前記場所が農業地区以外の場所であることを特徴とする請求項8に記載の 方法。 12.(a)請求項1に記載の式(I)の化合物と、 (b)ピペロニルブトキシド とから成る相乗的農薬組成物。 13.式(I)の化合物の製造方法であって、 (a)R1が水素を表す化合物を製造するために、式(II)のヒドラジン: 〔式中、X及びYは請求項1と同義〕またはその酸付加塩と、式(III): R2(R3)C=C(SOEt)(CN) (III) 〔式中、R2はシアノ、R3は塩素またはフッ素〕の化合物とを反応させる; (b)式(IV): 〔式中、R1、X及びYは請求項1と同義〕の化合物を酸化剤を用いて酸化させ る; (c)R1が水素を表す化合物を製造するために、式(V): 〔式中、X及びYは請求項1と同義〕の化合物と、式(VI): EtS(=O)CH2CN (VI) の化合物とを反応させる; (d)式(VII): 〔式中、X、Y及びR1は前記と同義〕の化倉物と、式EtS (O)Z1〔式中、Z1は離脱基〕の化合物とを反応させる; (e)R1がメチルまたはエチルを表す化合物を製造するために、R1が水素を表 す式(I)の対応する化合物とメチル化剤またはエチル化剤とを塩基の存在下で 反応させる; (f)R1がメチルまたはエチルを表す化合物を製造するために、R1が水素を表 す式(I)の対応する化合物と、R12がアルキルを表す式CH(OR12)3また はMeC(OR12)3のオルトホルメートとを反応させて式(VIII): 〔式中、R12は前記と同義、X及びYは請求項1と同義、R11は水素またはメチ ルを表す〕の化合物とし、次いでこれを還元剤で処理する;または (g)式(IX): 〔式中、X及びYは請求項1と同義、X1はハロゲンを表す〕の化合物と、式( X):〔式中、R1は請求項1と同義〕の化合物とを反応させる処理のいずれかを用い る方法。 14.式(VIII): 〔式中、R11は水素またはメチル、R12はアルキル、Xは塩素または臭素、Yは トリフルオロメチルまたはトリフルオロメトキシを表す〕の化合物。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US891395P | 1995-12-20 | 1995-12-20 | |
US60/008,913 | 1995-12-20 | ||
PCT/EP1996/005696 WO1997022593A1 (en) | 1995-12-20 | 1996-12-19 | Novel 5-amino-3-cyano-4-ethylsulfinyl-1-phenyl-pyrazole compounds and their use as pesticides |
Publications (2)
Publication Number | Publication Date |
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JP2000502095A true JP2000502095A (ja) | 2000-02-22 |
JP3986085B2 JP3986085B2 (ja) | 2007-10-03 |
Family
ID=21734438
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP52250897A Expired - Lifetime JP3986085B2 (ja) | 1995-12-20 | 1996-12-19 | 新規な5―アミノ―3―シアノ―4―エチルスルフィニル―1―フェニル―ピラゾール化合物及びその農薬としての使用 |
Country Status (54)
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2008504242A (ja) * | 2004-06-26 | 2008-02-14 | メリアル リミテッド | 殺虫剤としての1−アリールピラゾール誘導体 |
JP2010517977A (ja) * | 2007-02-06 | 2010-05-27 | ビーエーエスエフ ソシエタス・ヨーロピア | 殺害虫剤混合物 |
JP2011505396A (ja) * | 2007-12-05 | 2011-02-24 | バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト | 殺害虫性化合物混合物 |
JP2011505394A (ja) * | 2007-12-03 | 2011-02-24 | バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト | エチプロールおよび特定のカーバメートを含む殺害虫性化合物混合物 |
JPWO2009069676A1 (ja) * | 2007-11-28 | 2011-04-14 | 日本農薬株式会社 | 農園芸用殺虫剤組成物 |
JP2020532563A (ja) * | 2017-09-06 | 2020-11-12 | バイエル・アニマル・ヘルス・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングBayer Animal Health Gmbh | 動物寄生虫(animal parasites)の防除および予防のための局所投与製剤 |
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DK143796A (da) * | 1995-12-20 | 1997-06-21 | Rhone Poulenc Agrochimie | Nye pesticider |
ZA9711534B (en) | 1996-12-24 | 1998-06-24 | Rhone Poulenc Agrochimie | Pesticidal 1-arylpyrazoles. |
US6350771B1 (en) | 1996-12-24 | 2002-02-26 | Rhone-Poulenc, Inc. | Pesticidal 1-arylpyrazoles |
DK0976737T3 (da) | 1997-04-07 | 2009-07-20 | Nihon Nohyaku Co Ltd | Pyrazolderivater, fremgangsmåder til fremstilling deraf, intermediater og skadedyrsbekæmpelsesmidler indholdende disse som aktiv ingrediens |
US6107314A (en) | 1997-10-07 | 2000-08-22 | Rhone-Poulenc Inc. | Pesticides |
US5981565A (en) * | 1997-10-07 | 1999-11-09 | Rhone-Poulenc Inc. | Pyrazole pesticides |
ZA989421B (en) * | 1997-10-31 | 1999-04-21 | Sumitomo Chemical Co | Heterocyclic compounds |
DE19824487A1 (de) | 1998-06-02 | 1999-12-09 | Bayer Ag | Substituierte 3-Thiocarbamoylpyrazole |
US6855327B1 (en) * | 1998-07-02 | 2005-02-15 | Cognis Corporation | Pesticide dispersant |
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JP2008504242A (ja) * | 2004-06-26 | 2008-02-14 | メリアル リミテッド | 殺虫剤としての1−アリールピラゾール誘導体 |
JP2010517977A (ja) * | 2007-02-06 | 2010-05-27 | ビーエーエスエフ ソシエタス・ヨーロピア | 殺害虫剤混合物 |
JPWO2009069676A1 (ja) * | 2007-11-28 | 2011-04-14 | 日本農薬株式会社 | 農園芸用殺虫剤組成物 |
JP2011505394A (ja) * | 2007-12-03 | 2011-02-24 | バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト | エチプロールおよび特定のカーバメートを含む殺害虫性化合物混合物 |
JP2011505396A (ja) * | 2007-12-05 | 2011-02-24 | バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト | 殺害虫性化合物混合物 |
JP2020532563A (ja) * | 2017-09-06 | 2020-11-12 | バイエル・アニマル・ヘルス・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングBayer Animal Health Gmbh | 動物寄生虫(animal parasites)の防除および予防のための局所投与製剤 |
JP7305620B2 (ja) | 2017-09-06 | 2023-07-10 | バイエル・アニマル・ヘルス・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | 動物寄生虫(animal parasites)の防除および予防のための局所投与製剤 |
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