CA2494130C - Pyrazole derivatives and process for the production thereof - Google Patents

Pyrazole derivatives and process for the production thereof Download PDF

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Publication number
CA2494130C
CA2494130C CA2494130A CA2494130A CA2494130C CA 2494130 C CA2494130 C CA 2494130C CA 2494130 A CA2494130 A CA 2494130A CA 2494130 A CA2494130 A CA 2494130A CA 2494130 C CA2494130 C CA 2494130C
Authority
CA
Canada
Prior art keywords
group
general formula
pyrazole
chf2
trifluoromethyl
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 - Lifetime
Application number
CA2494130A
Other languages
English (en)
French (fr)
Other versions
CA2494130A1 (en
Inventor
Masao Nakatani
Minoru Ito
Masahiro Miyazaki
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.)
Ihara Chemical Industry Co Ltd
Kumiai Chemical Industry Co Ltd
Original Assignee
Ihara Chemical Industry Co Ltd
Kumiai Chemical Industry Co 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 Ihara Chemical Industry Co Ltd, Kumiai Chemical Industry Co Ltd filed Critical Ihara Chemical Industry Co Ltd
Publication of CA2494130A1 publication Critical patent/CA2494130A1/en
Application granted granted Critical
Publication of CA2494130C publication Critical patent/CA2494130C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • 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
    • C07D231/20—One oxygen atom attached in position 3 or 5
    • 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
    • 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
    • C07D231/20—One oxygen atom attached in position 3 or 5
    • C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
CA2494130A 2002-08-01 2003-07-31 Pyrazole derivatives and process for the production thereof Expired - Lifetime CA2494130C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP2002-225083 2002-08-01
JP2002225083 2002-08-01
PCT/JP2003/009762 WO2004013106A1 (ja) 2002-08-01 2003-07-31 ピラゾール誘導体及びその製造方法

Publications (2)

Publication Number Publication Date
CA2494130A1 CA2494130A1 (en) 2004-02-12
CA2494130C true CA2494130C (en) 2011-08-23

Family

ID=31492145

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2494130A Expired - Lifetime CA2494130C (en) 2002-08-01 2003-07-31 Pyrazole derivatives and process for the production thereof

Country Status (18)

Country Link
US (2) US7256298B2 (enExample)
EP (1) EP1541561B1 (enExample)
JP (1) JP4551764B2 (enExample)
KR (1) KR101031473B1 (enExample)
CN (2) CN1995021B (enExample)
AU (1) AU2003252447B2 (enExample)
BR (1) BR0313178B1 (enExample)
CA (1) CA2494130C (enExample)
ES (1) ES2519442T3 (enExample)
IL (2) IL166341A (enExample)
IN (1) IN2005CH00114A (enExample)
MX (1) MX255058B (enExample)
PL (1) PL218431B1 (enExample)
RS (1) RS53725B1 (enExample)
RU (1) RU2315758C2 (enExample)
TW (1) TW200409758A (enExample)
UA (1) UA79483C2 (enExample)
WO (1) WO2004013106A1 (enExample)

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DE10163079A1 (de) * 2001-12-20 2003-07-03 Basf Ag Verfahren zur Verbesserung des Pflanzenwachstums durch Applikation einer Mischung aus Schwefel und Komplexbildner
RS53725B1 (sr) * 2002-08-01 2015-06-30 Ihara Chemical Industry Co. Ltd. Derivati pirazola i postupak njihovog dobijanja
JP4621939B2 (ja) 2004-03-31 2011-02-02 イハラケミカル工業株式会社 ５−ヒドロキシ−４−チオメチルピラゾール化合物の製造方法
JP2007246396A (ja) * 2004-04-28 2007-09-27 Ihara Chem Ind Co Ltd ５−ジフルオロメトキシ−４−チオメチルピラゾール化合物の製造方法
RS51323B (sr) * 2004-09-03 2010-12-31 Syngenta Limited Derivati izoksazolona i njihova upotreba kao herbicida
ES2333977T3 (es) * 2004-10-05 2010-03-03 Syngenta Limited Derivados de isoxazolina y su uso como herbicidas.
RU2378261C2 (ru) * 2004-12-20 2010-01-10 Ихара Кемикал Индастри Ко., Лтд. Способ получения солевого соединения (4,5-дигидроизоксазол-3-ил)тиокарбоксамидина
MY144905A (en) * 2005-03-17 2011-11-30 Basf Ag Herbicidal compositions based on 3-phenyluracils and 3-sulfonylisoxazolines
DE102005031583A1 (de) * 2005-07-06 2007-01-25 Bayer Cropscience Gmbh Verfahren zur Herstellung von von 3-Arylmethylthio- und 3-Heteroarylmethylthio-4,5-dihydro-isoxazolin-Derivaten
JP2007031342A (ja) * 2005-07-27 2007-02-08 Ihara Chem Ind Co Ltd ５−ヒドロキシ−１−アルキルピラゾール誘導体の製造方法
GB0526044D0 (en) * 2005-12-21 2006-02-01 Syngenta Ltd Novel herbicides
AR059375A1 (es) * 2006-02-14 2008-03-26 Ihara Chemical Ind Co Procedimiento para produccion de 5-alcoxi-4-hidroximetilpirazol y compuestos
US8110530B2 (en) * 2006-12-21 2012-02-07 Kumiai Chemical Industry Co., Ltd. Herbicidal composition
DE102007012168A1 (de) 2007-03-12 2008-09-18 Bayer Cropscience Ag 2-[Heteroarylalkyl-sulfonyl]-thiazol-Derivate und 2-[Heteroarylalkyl-sulfinyl]-thiazol-Derivate, Verfahren zu deren Herstellung, sowie deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren
CN101367763B (zh) * 2007-08-17 2012-06-27 深圳泛胜塑胶助剂有限公司 1-苯基-3-甲基-5-吡唑酮的合成工艺
JP5295971B2 (ja) * 2007-10-18 2013-09-18 クミアイ化学工業株式会社 ３−アルコキシ−１−フェニルピラゾ−ル誘導体及び有害生物防除剤
EP2065374A1 (de) 2007-11-30 2009-06-03 Bayer CropScience AG 2-(Benzyl- und 1H-pyrazol-4-ylmethyl)sulfinyl-Thiazol-Derivate als Herbizide und Pflanzenwachstumsregulatoren
EP2065373A1 (de) 2007-11-30 2009-06-03 Bayer CropScience AG Chirale 3-(Benzylsulfinyl)-5,5-dimethyl-4,5-dihydroisoxazol-Derivate und 5,5-Dimethyl-3-[(1H-pyrazol-4-ylmethyl) sulfinyl]-4,5-dihydroisoxazol-Derivate, Verfahren zu deren Herstellung sowie deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren
EP2112143A1 (de) 2008-04-22 2009-10-28 Bayer CropScience AG 2-(Benzylsulfonyl)-Oxazol-Derivate, chirale 2-(Benzylsulfinyl)-Oxazol-Derivate 2-(Benzylsulfanyl-Oxazol Derivate, Verfahren zu deren Herstellung sowie deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren
EP2112149A1 (de) 2008-04-22 2009-10-28 Bayer CropScience Aktiengesellschaft 2-[(1h-Pyrazol-4-ylmethyl)-sulfonyl]-Oxazol-Derivate, 2-[(1H-Pyrazol-4-ylmethyl)-sulfanyl]-Oxazol-Derivate und chirale 2-[(1H-Pyrazol-4-ylmethyl)-sulfinyl]-Oxazol-Derivate, Verfahren zu deren Herstellung sowie deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren
ES2528646T3 (es) * 2010-05-20 2015-02-11 Bayer Intellectual Property Gmbh Procedimiento para la fabricación de 1-alquil-3-difluorometil-5-hidroxipirazoles
CN103145768B (zh) * 2013-03-06 2016-02-10 陕西科技大学 一种制备二茂铁甲醛的方法
BR112017003295A2 (pt) 2014-09-19 2018-01-23 Isagro Spa 1,3,4-tiadiazóis com uma atividade herbicida, suas composições agronômicas e uso relativo
JP6400247B1 (ja) * 2015-11-16 2018-10-03 ロンザ・リミテッド １−メチル−３−（トリフルオロメチル）−１ｈ−ピラゾール−５−オールの調製方法
RU2642924C1 (ru) * 2017-03-13 2018-01-30 Федеральное государственное бюджетное учреждение науки Институт органического синтеза им. И.Я. Постовского Уральского отделения Российской академии наук (ИОС УрО РАН) Способ получения 5-фенил-3-(трифторметил)-1н-пиразол-4-амина
CN109796408B (zh) * 2019-01-21 2022-04-15 江苏中旗科技股份有限公司 一种5-二氟甲氧基-3-三氟甲基-1-甲基吡唑的合成方法
IL290169B2 (en) * 2019-07-30 2025-04-01 Adama Agan Ltd Method and intermediates for preparing pyroxulfone
MX2022005121A (es) 2019-10-31 2022-12-13 Kumiai Chemical Industry Co Herbicida y método de producción para el intermediario del mismo.
AR121018A1 (es) * 2020-01-15 2022-04-06 Adama Agan Ltd Forma en estado sólido de piroxasulfona
BR112022017794A2 (pt) 2020-03-05 2022-10-25 Adama Agan Ltd Processo e intermediários para a preparação de piroxassulfona
EP3936503A1 (en) * 2020-07-10 2022-01-12 Adama Agan Ltd. Process and intermediates for the preparation of pyroxasulfone, fenoxasulfone and various sulfone analogs of 5,5-dimethyl-4h-1,2-oxazole
CN112110912B (zh) * 2020-07-31 2022-07-05 绍兴贝斯美化工股份有限公司 一种合成硫醚类中间体的方法
WO2022137370A1 (ja) * 2020-12-23 2022-06-30 クミアイ化学工業株式会社 スルホン誘導体の製造方法
CA3203529A1 (en) * 2021-01-19 2022-07-28 Daigo Itaya Method for controlling weeds
CN116709919A (zh) * 2021-01-19 2023-09-05 组合化学工业株式会社 杂草的防治方法
GB2603771A (en) * 2021-02-11 2022-08-17 Rotam Agrochem Int Co Ltd Novel crystalline form of pyroxa-sulfone, methods for its preparation and use of the same
US20240391909A1 (en) * 2021-10-29 2024-11-28 Kumiai Chemical Industry Co., Ltd. Disulfide compound, polysulfide compound, and use thereof
WO2023074828A1 (ja) 2021-10-29 2023-05-04 クミアイ化学工業株式会社 ジスルフィド化合物、ポリスルフィド化合物及びその用途
AR127776A1 (es) 2021-11-28 2024-02-28 Adama Agan Ltd Composiciones de concentrado en suspensión de alta carga
CN114213402A (zh) * 2021-12-01 2022-03-22 芮城华农生物化学有限公司 一种砜吡草唑亚稳态、稳定态晶型、制备方法及应用
WO2023194957A1 (en) * 2022-04-08 2023-10-12 Upl Limited A process for preparation of 3-[5-(difluoromethoxy)-1- methyl-3-(trifluoromethyl)pyrazol-4- ylmethylsulfonyl]-4,5-dihydro-5,5-dimethyl-1,2-oxazole and its intermediates
CN114989157A (zh) * 2022-06-28 2022-09-02 安徽久易农业股份有限公司 一种砜吡草唑的晶型a及其制备方法和应用
WO2024194794A1 (en) * 2023-03-20 2024-09-26 Upl Limited Process for preparation of pyroxasulfone and intermediates thereof
CN118221663A (zh) * 2024-05-24 2024-06-21 吉林凯莱英医药化学有限公司 砜吡草唑的连续化合成方法
CN120441564A (zh) * 2025-06-26 2025-08-08 济南大学 二氢异噁唑类化合物的晶型及其制备方法和应用

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IL85659A (en) * 1987-03-17 1992-03-29 Nissan Chemical Ind Ltd 4-benzoylpyrazole derivatives,method for their preparation and herbicidal compositions containing them
US5536701A (en) 1994-10-11 1996-07-16 Monsanto Company 3-pyrazolyloxypyridazines, herbicidal compositions and uses thereof
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RS53725B1 (sr) * 2002-08-01 2015-06-30 Ihara Chemical Industry Co. Ltd. Derivati pirazola i postupak njihovog dobijanja

Also Published As

Publication number Publication date
RS20050081A (sr) 2007-09-21
EP1541561B1 (en) 2014-07-23
TW200409758A (en) 2004-06-16
US20050215797A1 (en) 2005-09-29
EP1541561A1 (en) 2005-06-15
ES2519442T3 (es) 2014-11-07
EP1541561A4 (en) 2007-04-25
RU2315758C2 (ru) 2008-01-27
BR0313178B1 (pt) 2014-04-15
IN2005CH00114A (enExample) 2007-09-07
WO2004013106A1 (ja) 2004-02-12
MX255058B (es) 2008-03-04
AU2003252447A1 (en) 2004-02-23
TWI337997B (enExample) 2011-03-01
AU2003252447B2 (en) 2008-06-05
KR101031473B1 (ko) 2011-04-26
IL196010A0 (en) 2011-08-01
US7256298B2 (en) 2007-08-14
RS53725B1 (sr) 2015-06-30
JP4551764B2 (ja) 2010-09-29
CN1678588A (zh) 2005-10-05
BR0313178A (pt) 2005-06-14
PL218431B1 (pl) 2014-12-31
MXPA05001258A (es) 2005-04-28
CA2494130A1 (en) 2004-02-12
KR20050026082A (ko) 2005-03-14
US20070249844A1 (en) 2007-10-25
CN1995021B (zh) 2010-09-08
PL375319A1 (en) 2005-11-28
UA79483C2 (en) 2007-06-25
RU2005105585A (ru) 2005-08-27
JPWO2004013106A1 (ja) 2006-09-21
CN100548989C (zh) 2009-10-14
IL166341A (en) 2010-12-30
CN1995021A (zh) 2007-07-11
IL166341A0 (en) 2006-01-16

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