KR20050019777A - 헤테로사이클릭 플루오로알케닐 설폰의 제조방법 - Google Patents
헤테로사이클릭 플루오로알케닐 설폰의 제조방법 Download PDFInfo
- Publication number
- KR20050019777A KR20050019777A KR10-2004-7020932A KR20047020932A KR20050019777A KR 20050019777 A KR20050019777 A KR 20050019777A KR 20047020932 A KR20047020932 A KR 20047020932A KR 20050019777 A KR20050019777 A KR 20050019777A
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- South Korea
- Prior art keywords
- optionally
- alkyl
- hydrogen
- fluorine
- substituted
- Prior art date
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole 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
- C07D277/36—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole 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
- C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
Description
Claims (10)
- 임의로 반응 보조제의 존재하 및 임의로 희석제의 존재하에 일반식 (III)의 화합물을 퍼옥소모노설푸릭산(H2SO5)의 염과 반응시킴으로써 일반식 (I) 및 (II)의 화합물을 제조하는 방법:상기 식에서,R1은 수소 또는 불소이고,Het는 하기 그룹의 헤테로사이클로부터 선택되는 헤테로사이클이며;여기에서,R2는 수소, 할로겐, C1-C4-알킬 또는 C1-C4-할로알킬이고,R3는 수소, 할로겐, 및 또한 임의로 할로겐-, 메틸-, 에틸-, n- 또는 i-프로필- 또는 n-, i-, s- 또는 t-부틸-, 메톡시-, 에톡시-, n- 또는 i-프로폭시- 또는 n-, i-, s- 또는 t-부톡시-치환된 C1-C4-알킬, C1-C4-알콕시, C1-C4-알킬티오, C1-C4-알킬설피닐, C1-C4-알킬설포닐, C1-C4-알콕시카보닐, C1 -C4-알콕시-C1-C4-알킬, C1-C4-알킬티오-C1-C4-알킬, 카복실, C1-C4-알킬아미노카보닐, C 3-C6-사이클로알킬아미노카보닐, C1-C4-디알킬아미노카보닐, C2-C4-알케닐, C2-C 4-알케닐티오, C2-C4-알케닐설피닐 또는 C2-C4-알케닐설포닐이며,R4는 C1-C8-알킬, C2-C6-알케닐, C1-C 4-할로알킬, C1-C4-알콕시-C1-C4-알킬, C1 -C4-알킬티오-C1-C4-알킬, C3-C8-사이클로알킬 또는 임의로 할로겐-, C1-C4-알킬-, C1-C4-알콕시-, C1-C4-알킬티오- 또는 C1-C4-할로알킬-치환된 페닐 또는 벤질이고,p는 1, 2 또는 3이며,X는 산소 또는 황이고,Y는 각 경우에 임의로 할로겐-, C1-C4-알콕시-, C1-C4-알킬티오-, C1-C4-할로알콕시- 또는 C1-C4-할로알킬티오-치환된 C1-C4-알킬, C2 -C4-알케닐 또는 C2-C4-알키닐에 의해 임의로 단일 또는 이중으로 동일하거나 상이하게 치환된 메틸렌이거나, 또한 할로겐, 시아노, 니트로, C1-C4-알킬, C1-C4-알콕시, C 1-C4-알킬티오, C1-C4-할로알킬, C1-C4-할로알콕시 또는 C1-C4-할로알킬티오에 의해 임의로 단일 내지 삼중으로 동일하거나 상이하게 치환된 페닐이다.
- 제 1 항에 있어서, 임의로 반응 보조제의 존재하 및 임의로 희석제의 존재하에 제 1 항에 따른 일반식 (II)의 화합물을 퍼옥소모노설푸릭산(H2SO5)의 염과 반응시키는 것을 특징으로 하여 일반식 (I)의 화합물을 제조하는 방법.
- 제 2 항에 있어서, pH 6 내지 10에서 수행하는 것을 특징으로 하는 방법.
- 제 1 항에 있어서, 임의로 반응 보조제의 존재하 및 임의로 희석제의 존재하에 제 1 항에 따른 일반식 (III)의 화합물을 퍼옥소모노설푸릭산(H2SO5)의 염과 반응시키는 것을 특징으로 하여 일반식 (II)의 화합물을 제조하는 방법.
- 제 4 항에 있어서, pH 1 내지 3에서 수행하는 것을 특징으로 하는 방법.
- 제 1 항 내지 제 5 항중 어느 한 항에 있어서, 퍼옥소모노설푸릭산의 염이 포타슘 하이드로겐퍼옥소모노설페이트(2 KHSO5·KHSO4·K2SO4 (5:3:2:2)), 바람직하게는 Oxone?? 또는 Caroat??인 것을 특징으로 하는 방법.
- 제 1 항 내지 제 6 항중 어느 한 항에 있어서, 반응을 -20 내지 150 ℃의 온도에서 수행하는 것을 특징으로 하는 방법.
- 제 1 항 내지 제 7 항중 어느 한항에 있어서,R1이 불소이고,Het가 하기 그룹의 헤테로사이클로부터 선택되는 헤테로사이클이며;R2가 수소, 불소 또는 염소이고,R3가 수소, 불소, 염소, 및 또한 임의로 불소-, 염소-, 메틸-, 에틸-, n- 또는 i-프로필- 또는 n-, i-, s- 또는 t-부틸-, 메톡시-, 에톡시-, n- 또는 i-프로폭시- 또는 n-, i-, s- 또는 t-부톡시-치환된 메틸, 에틸, n- 또는 i-프로필, n-, i-, s- 또는 t-부틸, 메톡시, 에톡시, n- 또는 i-프로폭시, n-, i-, s- 또는 t-부톡시, 메틸티오, 에틸티오, n- 또는 i-프로필티오, n-, i-, s- 또는 t-부틸티오, 메틸설피닐, 에틸설피닐, 메틸설포닐, 에틸설포닐, 메톡시카보닐, 에톡시카보닐, n- 또는 i-프로폭시카보닐, n-, i-, s- 또는 t-부톡시카보닐, 메톡시메틸, 메톡시에틸, 에톡시메틸, 에톡시에틸, 메틸티오메틸, 메틸티오에틸, 에틸티오메틸, 에틸티오에틸, 카복실, 메틸아미노카보닐, 에틸아미노카보닐, n- 또는 i-프로필아미노카보닐, 사이클로프로필아미노카보닐, 사이클로부틸아미노카보닐, 사이클로펜틸아미노카보닐, 사이클로헥실아미노카보닐, 디메틸아미노카보닐, 디에틸아미노카보닐, 에테닐, 프로페닐 또는 부테닐이며,R4가 바람직하게는 메틸, 에틸, n-프로필, 이소프로필, n-부틸, 이소부틸, tert-부틸, n-펜틸, 사이클로프로필, 사이클로펜틸, 사이클로헥실, 2-클로로에틸, 2,2,3,3,3-펜타플루오로프로필, 2,2,2-트리플루오로에틸, 3-브로모프로필, 2-메톡시에틸, 2-에톡시에틸, 2-메틸티오에틸, 알릴, 2-부테닐, 또는 각 경우에 임의로 단일 또는 이중으로 동일하거나 상이하게 불소-, 염소-, 브롬-, 메틸-, 에틸-, 이소프로필-, 트리플루오로메틸-, 메톡시- 또는 메틸티오-치환된 페닐 또는 벤질이고,p가 1 또는 2이며,X가 산소이고,Y가 메틸, 에틸에 의해 임의로 단일 또는 이중으로 동일하거나 상이하게 치환된 메틸렌이거나, 불소, 염소, 메틸, 메톡시, 트리플루오로메틸, 시아노 또는 니트로에 의해 임의로 단일 또는 이중으로 동일하거나 상이하게 치환된 페닐인 것을 특징으로 하는 방법.
- 제 1 항 내지 제 8 항중 어느 한 항에 있어서,Het가 하기 그룹의 헤테로사이클로부터 선택되는 헤테로사이클이고;R2가 수소이며,R3가 수소, 불소 또는 염소인 것을 특징으로 하는 방법.
- 제 1 항 내지 제 9 항중 어느 한 항에 있어서,Het가 하기 헤테로사이클이고:R2가 수소이며,R3가 염소인 것을 특징으로 하는 방법.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10229776.2 | 2002-07-03 | ||
DE10229776A DE10229776A1 (de) | 2002-07-03 | 2002-07-03 | Verfahren zum Herstellen von heterocyclischen Fluoralkenylsulfonen |
PCT/EP2003/006511 WO2004005268A1 (de) | 2002-07-03 | 2003-06-20 | Verfahren zum herstellen von heterocyclischen fluoralkenylsulfonen |
Publications (2)
Publication Number | Publication Date |
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KR20050019777A true KR20050019777A (ko) | 2005-03-03 |
KR100874238B1 KR100874238B1 (ko) | 2008-12-16 |
Family
ID=29761584
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1020047020932A KR100874238B1 (ko) | 2002-07-03 | 2003-06-20 | 헤테로사이클릭 플루오로알케닐 설폰의 제조방법 |
Country Status (14)
Country | Link |
---|---|
US (1) | US8901311B2 (ko) |
EP (2) | EP1519928B1 (ko) |
JP (2) | JP4753579B2 (ko) |
KR (1) | KR100874238B1 (ko) |
CN (2) | CN1665795A (ko) |
AU (1) | AU2003245974A1 (ko) |
CY (1) | CY1115410T1 (ko) |
DE (1) | DE10229776A1 (ko) |
DK (1) | DK1519928T3 (ko) |
ES (1) | ES2485842T3 (ko) |
MX (1) | MXPA05000121A (ko) |
PT (1) | PT1519928E (ko) |
SI (1) | SI1519928T1 (ko) |
WO (1) | WO2004005268A1 (ko) |
Families Citing this family (13)
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DE10319590A1 (de) | 2003-05-02 | 2004-11-18 | Bayer Cropscience Ag | Wirkstoffkombinationen mit nematiziden und insektiziden Eigenschaften basierend auf Trifluorbutenyl-Verbindungen |
DE10319591A1 (de) | 2003-05-02 | 2004-11-18 | Bayer Cropscience Ag | Wirkstoffkombinationen mit nematiziden, insektiziden und fungiziden Eigenschaften basierend auf Trifluorbutenyl-Verbindungen |
CN102702133A (zh) * | 2012-01-10 | 2012-10-03 | 山东省联合农药工业有限公司 | 一种含噻唑的三氟丁烯类杀虫剂 |
CN103012386B (zh) * | 2012-12-26 | 2015-04-01 | 浙江普洛得邦制药有限公司 | 一种五元环状硫酸酯的制备方法 |
EP3386299B1 (en) | 2015-12-10 | 2024-04-24 | Adama Makhteshim Ltd. | Polyelectrolyte-layer forming block copolymers and compositions and uses thereof |
EP3419744B1 (de) | 2016-02-25 | 2021-05-12 | HWK Kronbichler GmbH | Zusammensetzung umfassend ein fluorhaltiges tensid |
IL267063A (en) * | 2016-12-09 | 2019-07-30 | Adama Makhteshim Ltd | Fluensulfone formulations in high concentration, their uses and processes for their preparation |
KR20200112816A (ko) * | 2017-12-20 | 2020-10-05 | 피아이 인더스트리스 엘티디. | 불소알킬 화합물의 제조와 사용방법 |
AR114185A1 (es) * | 2018-01-23 | 2020-07-29 | Adama Makhteshim Ltd | Síntesis de 5-cloro-2-[(3,4,4-trifluoro-3-buten-1-il)tio]-tiazol |
AR116506A1 (es) * | 2018-09-26 | 2021-05-12 | Adama Makhteshim Ltd | Proceso e intermediarios para la preparación de fluensulfona |
WO2020095161A1 (en) | 2018-11-05 | 2020-05-14 | Pi Industries Ltd. | Nitrone compounds and use thereof |
KR20210110792A (ko) * | 2018-12-31 | 2021-09-09 | 아다마 마켓심 리미티드 | 1,1,2-트리플루오로-4-(치환 설포닐)-부트-1-엔의 합성 |
WO2021024253A1 (en) | 2019-08-04 | 2021-02-11 | Yeda Research And Development Co. Ltd. | Process for the preparation of fluensulfone |
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WO1986007590A1 (en) | 1985-06-20 | 1986-12-31 | Fmc Corporation | Pesticidal polyhaloalkene derivatives |
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US5965737A (en) | 1999-02-17 | 1999-10-12 | Bayer Corporation | Approach to the conversion of 2-(methylthio)-5-(trifluoromethyl)-1,3,4-thiadiazole (TDA) to 2-(methylsulfonyl)-5-(trifluoromethyl)-1,3,4-thiadiazole (TDA sulfone) |
JP2001019685A (ja) * | 1999-07-06 | 2001-01-23 | Nippon Bayer Agrochem Co Ltd | 殺センチュウ性トリフルオロブテン類 |
JP2001322988A (ja) * | 2000-03-09 | 2001-11-20 | Nippon Bayer Agrochem Co Ltd | 殺センチュウ性トリフルオロブテン類 |
DE10031088C2 (de) | 2000-06-30 | 2002-12-19 | Raymond A & Cie | Beheizbare Scheibenwaschdüse |
DE10034133A1 (de) | 2000-07-13 | 2002-01-24 | Bayer Ag | Heterocyclische Fluoralkenylthioether (l) |
DE10034130A1 (de) * | 2000-07-13 | 2002-01-24 | Bayer Ag | Heterocyclische Fluoralkenylthioether (lV) |
DE10034132A1 (de) * | 2000-07-13 | 2002-01-24 | Bayer Ag | Heterocyclische Fluoralkenylthioether (lll) |
DE10034131A1 (de) | 2000-07-13 | 2002-01-24 | Bayer Ag | Heterocyclische Fluoralkenylthioether (II) |
DE10201238A1 (de) * | 2002-01-15 | 2003-07-24 | Bayer Cropscience Ag | Verfahren zur Herstellung von halogenierten 2-(3-Butenylsulfanyl)-1,3-thiazolen |
TWI270542B (en) * | 2002-02-07 | 2007-01-11 | Sumitomo Chemical Co | Method for preparing sulfone or sulfoxide compound |
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2002
- 2002-07-03 DE DE10229776A patent/DE10229776A1/de not_active Withdrawn
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2003
- 2003-06-20 CN CN038157225A patent/CN1665795A/zh active Pending
- 2003-06-20 DK DK03738072.2T patent/DK1519928T3/da active
- 2003-06-20 SI SI200332366T patent/SI1519928T1/sl unknown
- 2003-06-20 WO PCT/EP2003/006511 patent/WO2004005268A1/de active Application Filing
- 2003-06-20 EP EP03738072.2A patent/EP1519928B1/de not_active Expired - Lifetime
- 2003-06-20 PT PT37380722T patent/PT1519928E/pt unknown
- 2003-06-20 KR KR1020047020932A patent/KR100874238B1/ko active IP Right Grant
- 2003-06-20 CN CN201510100450.2A patent/CN104761512A/zh active Pending
- 2003-06-20 ES ES03738072.2T patent/ES2485842T3/es not_active Expired - Lifetime
- 2003-06-20 JP JP2004518547A patent/JP4753579B2/ja not_active Expired - Fee Related
- 2003-06-20 US US10/518,454 patent/US8901311B2/en not_active Expired - Lifetime
- 2003-06-20 EP EP10178611A patent/EP2258693A1/de not_active Withdrawn
- 2003-06-20 AU AU2003245974A patent/AU2003245974A1/en not_active Abandoned
- 2003-06-20 MX MXPA05000121A patent/MXPA05000121A/es unknown
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2010
- 2010-10-29 JP JP2010243111A patent/JP2011063599A/ja not_active Withdrawn
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2014
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Publication number | Publication date |
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US20060004196A1 (en) | 2006-01-05 |
JP4753579B2 (ja) | 2011-08-24 |
ES2485842T3 (es) | 2014-08-14 |
AU2003245974A1 (en) | 2004-01-23 |
CY1115410T1 (el) | 2017-01-04 |
WO2004005268A1 (de) | 2004-01-15 |
SI1519928T1 (sl) | 2014-10-30 |
JP2005537249A (ja) | 2005-12-08 |
EP1519928A1 (de) | 2005-04-06 |
MXPA05000121A (es) | 2005-04-08 |
EP1519928B1 (de) | 2014-04-30 |
JP2011063599A (ja) | 2011-03-31 |
DK1519928T3 (da) | 2014-08-04 |
PT1519928E (pt) | 2014-08-01 |
DE10229776A1 (de) | 2004-01-22 |
CN1665795A (zh) | 2005-09-07 |
CN104761512A (zh) | 2015-07-08 |
EP2258693A1 (de) | 2010-12-08 |
US8901311B2 (en) | 2014-12-02 |
KR100874238B1 (ko) | 2008-12-16 |
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