JPS6348865B2 - - Google Patents

Info

Publication number
JPS6348865B2
JPS6348865B2 JP3206879A JP3206879A JPS6348865B2 JP S6348865 B2 JPS6348865 B2 JP S6348865B2 JP 3206879 A JP3206879 A JP 3206879A JP 3206879 A JP3206879 A JP 3206879A JP S6348865 B2 JPS6348865 B2 JP S6348865B2
Authority
JP
Japan
Prior art keywords
trifluoromethyl
chloro
pyridone
yloxy
melting point
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
JP3206879A
Other languages
English (en)
Other versions
JPS55124763A (en
Inventor
Ryuzo Nishama
Kanichi Fujikawa
Isao Yokomichi
Takahiro Haga
Kuniaki Hase
Hirohito Hayashi
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Ishihara Sangyo Kaisha Ltd
Original Assignee
Ishihara Sangyo Kaisha Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ishihara Sangyo Kaisha Ltd filed Critical Ishihara Sangyo Kaisha Ltd
Priority to JP3206879A priority Critical patent/JPS55124763A/ja
Priority to DE19803008908 priority patent/DE3008908A1/de
Priority to GB8007881A priority patent/GB2049666B/en
Priority to CA000347559A priority patent/CA1134833A/en
Priority to CH203480A priority patent/CH642355A5/de
Priority to IT48176/80A priority patent/IT1147077B/it
Priority to BE0/199840A priority patent/BE882284A/fr
Priority to FR8006030A priority patent/FR2451917A1/fr
Priority to US06/131,719 priority patent/US4546191A/en
Priority to NL8001618A priority patent/NL8001618A/nl
Publication of JPS55124763A publication Critical patent/JPS55124763A/ja
Publication of JPS6348865B2 publication Critical patent/JPS6348865B2/ja
Granted legal-status Critical Current

Links

Classifications

    • 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/70—Sulfur atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyridine Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Description

【発明の詳細な説明】 本発明は医薬、農薬、染料などの中間原料とし
て有用で、新規な５―トリフルオロメチル―２―
ピリドン誘導体に関する。
詳しくは本発明は一般式 （式中Ｘは水素原子であり、Ｙはイオウ原子で
ある。）で表わされる５―トリフルオロメチル―
２―ピリドン誘導体である。
前記一般式（）の５―トリフルオロメチル―
２―ピリドン誘導体は、次に示すような互変異性
として存在することができる。
（式中Ｘ及びＹは前述の通りである） 本発明の５―トリフルオロメチル―２―ピリド
ン誘導体は通常、例えば下記方法によつて製造さ
れる。
（上記反応式中Halはハロゲン原子である） 一般に上記反応はジメチルスルホキシド、ジメ
チルホルムアミドなどの非プロトン性極性溶媒
中、水酸化ナトリウム、水酸化カリウムなどのア
リカリ水溶液を用いて50〜150℃、0.1〜10時間で
行われる。
（上記反応式中Ｘ及びHalは前述の通りであ
る） 一般に上記反応はメタノール、エタノールなど
のアルコール類、ジメチルスルホキシド、ジメチ
ルホルムアミドなどの非プロトン性極性溶媒など
の溶媒中、チオ尿素、硫化ソーダ、チオ硫酸ソー
ダ、Ｎ，Ｎ―ジメチルジチオカルバミン酸ソーダ
などのチオール化剤を用いて50〜還流温度0.5〜
10時間で行われる。
（上記反応式中Ｙ及びHalは前述の通りであ
る） 一般に上記反応は四塩化炭素、クロロホルム、
酢酸、二硫化炭素、水、非プロトン性極性溶媒な
どの溶媒中、塩素ガス、臭素、チオニルクロライ
ド、スルフリルクロライドなどのハロゲン化剤を
用いて０〜100℃、0.5〜10時間で行われる。
本発明化合物は、例えばハロゲン化ニトロベン
ゼン類と縮合させて４―（５―トリフルオロメチ
ルピリジン―２―イルオキシ又は２―イルチオ）
ニトロベンゼン類を生成させ、これを還元して得
られる４―（５―トリフルオロメチルピリジン―
２―イルオキシ又は２―イルチオ）アニリン類と
ベンゾイルイソシアネート類とを反応させること
によりＮ―ベンゾイル―N′―〔４―（５―トリ
フルオロメチルピリジン―２―イルオキシ又は２
―イルチオ）フエニル〕ウレア系化合物に誘導で
きる。詳しくは本発明化合物の３―クロロ―５―
トリフルオロメチル―２―ピリドン又は５―トリ
フルオロメチル―２―チオピリドンと３，４，５
―トリクロロニトロベンゼン又は３，４―ジクロ
ロニトロベンゼンとを縮合、還元してそれぞれ
３，５―ジクロロ―４―（３―クロロ―５―トリ
フルオロメチルピリジン―２―イルオキシ）アニ
リン又は３―クロロ―４―（５―トリフルオロメ
チルピリジン―２―イルチオ）アニリンを得、更
にこれらのものと２，６―ジフルオロベンゾイル
イソシアネートとを反応させると、Ｎ―（２，６
―ジフルオロベンゾイル）―N′―〔３，５―ジ
クロロ―４―（３―クロロ―５―トリフルオロメ
チルピリジン―２―イルオキシ）フエニル〕ウレ
ア（融点203〜205℃）（化合物Ａ）又はＮ―（２，
６―ジフルオロベンゾイル）―N′―〔３―クロ
ロ―４―（５―トリフルオロメチルピリジン―２
―イルチオ）フエニル〕ウレア（融点184〜188
℃）（化合物Ｂ）をそれぞれ得ることができる。
これらのものは殺虫剤の有効成分として優れた活
性を示し、種々の有害虫、特に有害昆虫の防除に
有効であつて、例えば化合物Ａの100ppm及び化
合物Ｂの400ppm水分散液にキヤベツの葉片を浸
漬し、それを風乾してそこへ２〜３令のコナガの
幼虫を放ち、８日目に生死を判定した結果、それ
ぞれ100％及び80％の死虫率が得られた。
次に本発明化合物の具体的合成例を記載する。
合成例 １ ３―クロロ―５―トリフルオロメチル―２―ピ
リドン （参考） ５―トリフルオロメチル―２―ピリドン0.2ｇ
をクロロホルム20mlに溶解させ、50℃に加温して
塩素ガスを１時間撹拌下に通じた。反応終了後、
クロロホルムを留去し、トルエン―ｎ―ヘキサン
の混合溶媒で再結晶して融点144〜147℃の目的物
0.15ｇを得た。
合成例 ２ ５―トリフルオロメチル―２―チオピリドン ２―クロロ―５―トリフルオロメチルピリジン
４ｇとチオ尿素1.67ｇとをエタノール30mlに溶解
させ、加熱して還流状態で３時間撹拌下に反応さ
せた。その後、水酸化カリウム水溶液1.23ｇを
徐々に加えて還流状態で１時間反応させた。反応
終了後、生成物を放冷し、希アルカリ水溶液中に
投入して塩化メチレンで洗浄し、酢酸で酸性にし
た。次いで、塩化メチレンで抽出し、抽出層を水
洗後無水硫酸ナトリウムで乾燥させ、塩化メチレ
ンを留去して融点147〜150℃の目的物2.1ｇを得
た。
合成例 ３ ３―ブロモー５―トリフルオロメチル―２―ピ
リドン （参考） ５―トリフルオロメチル―２―ピリドン0.4ｇ
を酢酸10mlに溶解させ、そこへ臭素0.4ｇを加え
て撹拌下で４時間反応させた。反応終了後、酢酸
を留去し、塩化メチレン―ｎ―ヘキサンの混合溶
媒で再結晶して融点162〜165℃の目的物0.45ｇを
得た。
合成例 ４ ３―クロロ―５―トリフルオロメチル―２―チ
オピリドン （参考） ２―クロロ―５―トリフルオロメチルピリジン
４ｇに代えて２，３―ジクロロ―５―トリフルオ
ロメチルピリジン4.75ｇを用いる以外は前記合成
例2.と同様にして反応を行い、後処理を行つて融
点125〜128℃の目的物1.9ｇを得た。

Claims (1)

  1. 【特許請求の範囲】 １ 一般式 （式中Ｘは水素原子であり、Ｙはイオウ原子で
    ある。）で表わされる５―トリフルオロメチル―
    ２―ピリドン誘導体。
JP3206879A 1979-03-19 1979-03-19 5-trifluoromethyl-2-pyridone derivative Granted JPS55124763A (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
JP3206879A JPS55124763A (en) 1979-03-19 1979-03-19 5-trifluoromethyl-2-pyridone derivative
DE19803008908 DE3008908A1 (de) 1979-03-19 1980-03-07 Trifluoromethyl-2-(thio)-pyridon- verbindungen und verfahren zu deren herstellung
GB8007881A GB2049666B (en) 1979-03-19 1980-03-07 Trifluoromethyl-2-(thio) pyridone compound and process forpreparing the same
CA000347559A CA1134833A (en) 1979-03-19 1980-03-13 Trifluoromethyl-2-(thio)pyridone compounds and process for the preparation of the same
CH203480A CH642355A5 (de) 1979-03-19 1980-03-14 Trifluormethyl-2-(thio)-pyridon-verbindungen und verfahren zu deren herstellung.
IT48176/80A IT1147077B (it) 1979-03-19 1980-03-17 Composti di tricloronetil-2-(tio)-piridone e procedimento per prepararli
BE0/199840A BE882284A (fr) 1979-03-19 1980-03-18 COMPOSES DE TRIFLUOROMETHYL-2(THIO)pYRIDONE ET LEUR PROCEDE DE PREPARATION
FR8006030A FR2451917A1 (fr) 1979-03-19 1980-03-18 Composes de trifluoromethyl-2-(thio) pyridone et leur preparation
US06/131,719 US4546191A (en) 1979-03-19 1980-03-19 Trifluoromethyl-2-pyridinone or pyridinthione compounds and process for the preparation of the same
NL8001618A NL8001618A (nl) 1979-03-19 1980-03-19 Trifluormethyl-2-(thio)pyridonverbindingen en werkwijze voor het bereiden en toepassen van deze verbindingen.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP3206879A JPS55124763A (en) 1979-03-19 1979-03-19 5-trifluoromethyl-2-pyridone derivative

Related Child Applications (1)

Application Number Title Priority Date Filing Date
JP16459486A Division JPS6226270A (ja) 1986-07-15 1986-07-15 ５−トリフルオロメチル−２−ピリドン誘導体

Publications (2)

Publication Number Publication Date
JPS55124763A JPS55124763A (en) 1980-09-26
JPS6348865B2 true JPS6348865B2 (ja) 1988-09-30

Family

ID=12348551

Family Applications (1)

Application Number Title Priority Date Filing Date
JP3206879A Granted JPS55124763A (en) 1979-03-19 1979-03-19 5-trifluoromethyl-2-pyridone derivative

Country Status (10)

Country Link
US (1) US4546191A (ja)
JP (1) JPS55124763A (ja)
BE (1) BE882284A (ja)
CA (1) CA1134833A (ja)
CH (1) CH642355A5 (ja)
DE (1) DE3008908A1 (ja)
FR (1) FR2451917A1 (ja)
GB (1) GB2049666B (ja)
IT (1) IT1147077B (ja)
NL (1) NL8001618A (ja)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3308800A1 (de) * 1983-03-12 1984-09-13 Rütgerswerke AG, 6000 Frankfurt Verfahren zur herstellung von 3,5,6-trichlor-1h-pyridin-2-on
GB8523126D0 (en) * 1985-09-19 1985-10-23 Ici Plc Aryl pyridones
GB8621217D0 (en) * 1986-09-03 1986-10-08 Ici Plc Chemical compounds
US7517880B2 (en) * 1997-12-22 2009-04-14 Bayer Pharmaceuticals Corporation Inhibition of p38 kinase using symmetrical and unsymmetrical diphenyl ureas
US7329670B1 (en) 1997-12-22 2008-02-12 Bayer Pharmaceuticals Corporation Inhibition of RAF kinase using aryl and heteroaryl substituted heterocyclic ureas
US20080269265A1 (en) * 1998-12-22 2008-10-30 Scott Miller Inhibition Of Raf Kinase Using Symmetrical And Unsymmetrical Substituted Diphenyl Ureas
EP2298311B1 (en) * 1999-01-13 2012-05-09 Bayer HealthCare LLC w-Carboxy aryl substituted diphenyl ureas as p38 kinase inhibitors
US8124630B2 (en) 1999-01-13 2012-02-28 Bayer Healthcare Llc ω-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors
US7351834B1 (en) 1999-01-13 2008-04-01 Bayer Pharmaceuticals Corporation ω-Carboxyaryl substituted diphenyl ureas as raf kinase inhibitors
EP1140840B1 (en) * 1999-01-13 2006-03-22 Bayer Pharmaceuticals Corp. -g(v)-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors
WO2002012243A2 (en) * 2000-08-09 2002-02-14 Boehringer Ingelheim Pharmaceuticals, Inc. SYNTHESIS OF (R)-3-(4-BROMOBENZYL)-1-(3,5-DICHLOROPHENYL)-5-IODO-3-METHYL-1-H-IMIDAZO[1,2-a]IMIDAZOL-2-ONE
EP2305255B1 (en) * 2001-12-03 2012-08-22 Bayer HealthCare LLC Aryl urea compounds in combination with other cytostatic or cytotoxic agents for treating human cancers
US20030207872A1 (en) * 2002-01-11 2003-11-06 Bayer Corporation Omega-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors
ATE529406T1 (de) * 2002-02-11 2011-11-15 Bayer Healthcare Llc Aryl-harnstoffe als kinase inhibitoren
DK1478358T3 (da) 2002-02-11 2013-10-07 Bayer Healthcare Llc Sorafenibtosylat til behandling af sygdomme kendetegnet ved unormal angiogenese
UY28213A1 (es) 2003-02-28 2004-09-30 Bayer Pharmaceuticals Corp Nuevos derivados de cianopiridina útiles en el tratamiento de cáncer y otros trastornos.
EP1636585B2 (en) 2003-05-20 2012-06-13 Bayer HealthCare LLC Diaryl ureas with kinase inhibiting activity
PL1663978T3 (pl) 2003-07-23 2008-04-30 Bayer Healthcare Llc Fluoropodstawiony omega-karboksyarylodifenylomocznik do leczenia i profilaktyki chorób i stanów
CN102875453B (zh) * 2012-06-08 2016-02-03 上海泰坦化学有限公司 一种用于合成抗癌辅助类药物的吡啶类医药中间体的制备方法

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US3355278A (en) * 1961-03-13 1967-11-28 Hooker Chemical Corp Herbicidal composition and method
US3634435A (en) * 1968-07-10 1972-01-11 Sandoz Ltd Certain s-(n-methylene-pyridone - (2)-o o-dilower-alkyl mono and dithio phosphates and derivatives
US3682938A (en) * 1970-12-18 1972-08-08 Dow Chemical Co Bis(trifluoro methyl)-2-pyridinols
AR208500A1 (es) * 1972-06-14 1977-02-15 Merck & Co Inc Procedimiento para la preparacion de derivados de oxazolo(4,5-b)-piridinas
US3974166A (en) * 1973-07-10 1976-08-10 Ciba-Geigy Corporation Process for the manufacture of bromopyridines
DE2531202C2 (de) * 1975-07-12 1982-12-09 Bayer Ag, 5090 Leverkusen 2',4-Dichlor-4'-benzoylureido- diphenyläther, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide
JPS5840946B2 (ja) * 1976-10-29 1983-09-08 石原産業株式会社 Ｎ−ベンゾイル−ｎ′−ピリジルオキシフエニルウレア系化合物、それらの製造方法及びそれらを含有する殺虫剤
JPS5461182A (en) * 1977-10-20 1979-05-17 Ishihara Sangyo Kaisha Ltd 2-phenoxy-5-trifluoromethylpyridine compounds
JPS5461183A (en) * 1977-10-21 1979-05-17 Ishihara Sangyo Kaisha Ltd 2-substituted-5-trifluoromethyl pyridine compounds
BE862325A (fr) * 1977-12-27 1978-06-27 Ciba Geigy Nouveaux derives d'acide pyridyloxy-phenoxypropionique ayant une action herbicide et phytoregulatrice
US4230864A (en) * 1979-01-29 1980-10-28 Reilly Tar & Chemical Corp. Process for making 5-trifluoromethyl pyridone
US4249009A (en) * 1979-01-29 1981-02-03 Reilly Tar & Chemical Corp. Processes for preparing 2-chloro-5-trifluoromethylpyridine

Also Published As

Publication number Publication date
FR2451917B1 (ja) 1983-04-22
IT8048176A0 (it) 1980-03-17
IT1147077B (it) 1986-11-19
DE3008908A1 (de) 1980-10-02
GB2049666A (en) 1980-12-31
NL8001618A (nl) 1980-09-23
DE3008908C2 (ja) 1989-09-21
CH642355A5 (de) 1984-04-13
JPS55124763A (en) 1980-09-26
BE882284A (fr) 1980-07-16
GB2049666B (en) 1983-04-27
CA1134833A (en) 1982-11-02
US4546191A (en) 1985-10-08
FR2451917A1 (fr) 1980-10-17

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