ES2526140T3 - Procedimiento para la síntesis de fipronil - Google Patents

Procedimiento para la síntesis de fipronil Download PDF

Info

Publication number
ES2526140T3
ES2526140T3 ES10846930.5T ES10846930T ES2526140T3 ES 2526140 T3 ES2526140 T3 ES 2526140T3 ES 10846930 T ES10846930 T ES 10846930T ES 2526140 T3 ES2526140 T3 ES 2526140T3
Authority
ES
Spain
Prior art keywords
formula
compound
perhalogenoalkyl
halogen
perhalogenoalkylaniline
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.)
Active
Application number
ES10846930.5T
Other languages
English (en)
Inventor
Keki Hormusji Gharda
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.)
Individual
Original Assignee
Individual
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=42262149&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=ES2526140(T3) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Individual filed Critical Individual
Application granted granted Critical
Publication of ES2526140T3 publication Critical patent/ES2526140T3/es
Active legal-status Critical Current
Anticipated expiration legal-status Critical

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
    • C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Un procedimiento para preparar un compuesto de trifluorometilsulfinilpirazol de fórmula I,**Fórmula** en donde R1 y R2, contienen elementos de grupo halógeno respectivamente, y R3 es un perhalogenoalquilo; comprendiendo dicho procedimiento: a) halogenar un compuesto aromático de fórmula II:**Fórmula** en donde, R es un halógeno y R3 es un perhalogenoalquilo, para obtener un compuesto de perhalogenoalquilbenceno polihalogenado de fórmula III;**Fórmula** en donde R, R2 contienen elementos de grupo halógeno respectivamente; y R3 es un perhalogenoalquilo, b) hacer reaccionar, en un disolvente polar seleccionado de un grupo que consiste en N-metilpirrolidona, dimetilsulfona, N,N'-dimetilimidazolidinona y difenilsulfona, preferiblemente N-metilpirrolidona, el compuesto de fórmula III con amoniaco anhidro en presencia de un haluro alcalino, preferiblemente fluoruro potásico; a una temperatura de aproximadamente 200ºC a 300ºC, preferiblemente en el intervalo de 235ºC a 250ºC; y una presión de aproximadamente 1,96 MPa (20 kg/cm2) a aproximadamente 4,90 MPa (50 kg/cm2), preferiblemente en el intervalo de 2,45 MPa (25 kg/cm2) a aproximadamente 4,11 MPa (42 kg/cm2) para obtener un compuesto de halogeno-perhalogenoalquilanilina de fórmula IV:**Fórmula** en donde R2 es halógeno y R3 es un perhalogenoalquilo. c) hacer reaccionar el compuesto de halogeno-perhalogenoalquilanilina de fórmula IV con al menos un agente de halogenación seleccionado de un grupo que consiste en cloro, cloruro de sulfurilo, cloruro de tionilo y pentacloruro de fósforo; preferiblemente cloruro de sulfurilo, en un disolvente clorado seleccionado de un grupo que consiste en cloroformo, dicloroetano, diclorometano, clorobenceno y o-diclorobenceno, para obtener una mezcla de productos que contiene el compuesto de perhalogenoalquilanilina polihalogenado de fórmula V;**Fórmula** en donde R1 y R2 contienen elementos de grupo halógeno respectivamente; y R3 es un perhalogenoalquilo; d) aislar el compuesto de perhalogenoalquilanilina polihalogenado de fórmula V de la mezcla de productos, preferiblemente por destilación fraccionada; e) diazotar el compuesto de anilina polihalogenado de fórmula V aislado con ácido nitrosil-sulfúrico en presencia de un disolvente ácido para formar un derivado diazotado del compuesto V;**Fórmula** f) hacer reaccionar el derivado diazotado del compuesto V con derivado de ciano-propionato de alquilo y amoniaco a una temperatura en el intervalo de aproximadamente 0ºC a 25ºC para obtener una mezcla de reacción que contiene el compuesto de pirazol de fórmula VII;**Fórmula**

Description

imagen1
imagen2
imagen3
imagen4
imagen5
imagen6
imagen7
imagen8
imagen9
imagen10

Claims (1)

  1. imagen1
    imagen2
    imagen3
    imagen4
ES10846930.5T 2010-03-03 2010-07-28 Procedimiento para la síntesis de fipronil Active ES2526140T3 (es)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
INMU05522010 2010-03-03
IN552MU2010 2010-03-03
PCT/IN2010/000496 WO2011107998A1 (en) 2010-03-03 2010-07-28 Process for synthesis of fipronil

Publications (1)

Publication Number Publication Date
ES2526140T3 true ES2526140T3 (es) 2015-01-07

Family

ID=42262149

Family Applications (1)

Application Number Title Priority Date Filing Date
ES10846930.5T Active ES2526140T3 (es) 2010-03-03 2010-07-28 Procedimiento para la síntesis de fipronil

Country Status (11)

Country Link
US (1) US8507693B2 (es)
EP (1) EP2542531B1 (es)
CN (1) CN102781920B (es)
AR (1) AR080017A1 (es)
AU (2) AU2010100462A4 (es)
BR (1) BRPI1004117A2 (es)
CH (1) CH701924B1 (es)
DK (1) DK2542531T3 (es)
ES (1) ES2526140T3 (es)
PL (1) PL2542531T3 (es)
WO (1) WO2011107998A1 (es)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1400666B1 (it) 2010-07-07 2013-06-28 Finchimica Srl Procedimento per la sintesi di 5-amino, 1-fenil, 3-ciano, 4-trifluorometil sulfinil pirazoli.
CN102633722B (zh) * 2012-03-20 2015-05-06 金坛市凌云动物保健品有限公司 一种非泼罗尼的制备方法
WO2014163933A1 (en) * 2013-03-13 2014-10-09 Dow Agrosciences Llc Process for preparation of triaryl pesticide intermediate
WO2014163932A1 (en) * 2013-03-13 2014-10-09 Dow Agrosciences Llc Preparation of haloalkoxyarylhydrazines and intermediates therefrom
CN103214395B (zh) * 2013-03-26 2014-04-30 南通市海圣药业有限公司 2,3-二氰基丙酸乙酯的合成工艺
CN105636445B (zh) 2013-10-17 2018-12-07 美国陶氏益农公司 制备杀虫化合物的方法
JP6730309B2 (ja) 2015-04-08 2020-07-29 バイエル・クロップサイエンス・アクチェンゲゼルシャフト 有害生物防除剤としての縮合二環式ヘテロ環誘導体及び中間体生成物
AU2016307233B2 (en) 2015-08-07 2020-12-24 Bayer Cropscience Aktiengesellschaft 2-(het)aryl-substituted condensed heterocyclic derivatives as pest control agents
AU2016347345B2 (en) 2015-10-26 2020-06-25 Bayer Cropscience Aktiengesellschaft Condensed bicyclic heterocycle derivatives as pest control agents
CN106117145A (zh) * 2016-07-12 2016-11-16 潍坊鑫诺化工有限公司 5‑氨基‑1‑（2,6‑二氯‑4‑三氟甲基苯基）‑3‑氰基吡唑的制备方法
US10233155B2 (en) 2016-12-29 2019-03-19 Dow Agrosciences Llc Processes for the preparation of pesticide compounds
WO2018138050A1 (de) 2017-01-26 2018-08-02 Bayer Aktiengesellschaft Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel
CN107353251A (zh) * 2017-07-24 2017-11-17 连云港埃森化学有限公司 一种氟虫腈生产工艺
WO2019097306A2 (en) * 2017-11-15 2019-05-23 Adama Makhteshim, Ltd. Synthesis of 5-amino-1-(2,6-dichloro-4-trifluoromethyl-phenyl)-4-ethylsulfanyl-1h-pyrazole-3-carbonitrile and related compounds
CN111989328B (zh) 2018-04-20 2023-04-18 拜耳公司 作为害虫防治剂的杂环衍生物
WO2020173861A1 (de) 2019-02-26 2020-09-03 Bayer Aktiengesellschaft Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel
WO2020173860A1 (en) 2019-02-26 2020-09-03 Bayer Aktiengesellschaft Fused bicyclic heterocycle derivatives as pesticides
CN111689899B (zh) * 2019-03-14 2023-06-02 上海出入境检验检疫局动植物与食品检验检疫技术中心 一种稳定同位素标记的氟虫腈和其衍生物以及合成制备方法
EP3941907A4 (en) * 2019-03-19 2023-01-04 Gharda Chemicals Limited FIPRONIL SYNTHESIS METHOD

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB8400886D0 (en) 1984-01-13 1984-02-15 Ici Plc Chemical process
GB8713768D0 (en) * 1987-06-12 1987-07-15 May & Baker Ltd Compositions of matter
FR2787445B1 (fr) 1998-12-17 2001-01-19 Rhone Poulenc Agrochimie Procede de preparation de para-trifluoromethylanilines polyhalogenees
GB9907458D0 (en) * 1999-03-31 1999-05-26 Rhone Poulenc Agrochimie Processes for preparing pesticidal intermediates
DE69919599T2 (de) 1999-10-22 2005-08-11 Bayer Cropscience S.A. Verfahren zur herstellung von 4-trifluormethylsulfinylpyrazolderivat
KR101437704B1 (ko) * 2006-07-05 2014-09-04 아벤티스 애그리컬쳐 1-아릴-5-알킬 피라졸 유도체 화합물, 이의 제조 방법 및 이의 사용 방법
CN101289400B (zh) * 2008-03-24 2011-07-20 浙江巍华化工有限公司 一种合成2,6-二氯-4-三氟甲基苯胺的方法
AU2010100312A6 (en) * 2009-11-12 2010-08-12 Keki Hormusji Gharda A process for preparing polyhalogenated perhalo alkyl aniline

Also Published As

Publication number Publication date
EP2542531A1 (en) 2013-01-09
CH701924B1 (de) 2011-03-15
US20130030190A1 (en) 2013-01-31
AU2010100871A4 (en) 2010-10-14
EP2542531A4 (en) 2013-08-14
US8507693B2 (en) 2013-08-13
EP2542531B1 (en) 2014-09-17
PL2542531T3 (pl) 2015-03-31
CN102781920A (zh) 2012-11-14
BRPI1004117A2 (pt) 2013-02-26
CN102781920B (zh) 2015-05-20
AU2010100462A4 (en) 2010-06-17
DK2542531T3 (en) 2015-01-05
AR080017A1 (es) 2012-03-07
WO2011107998A1 (en) 2011-09-09

Similar Documents

Publication Publication Date Title
ES2526140T3 (es) Procedimiento para la síntesis de fipronil
KR101609891B1 (ko) 2-아미노-5-시아노벤조산 유도체의 제조 방법
CN106029618B (zh) 生产2,5-二卤代酚醚的方法
Khatun et al. A one-pot strategy for the synthesis of 2-aminobenzothiazole in water by copper catalysis
CN104447396A (zh) 一种安息香肟衍生物及其制备方法
He et al. Substrate-promoted ligand-free CuI catalyzed S-arylation of 2-mercaptobenzothiazoles with aryl iodides in water
Borys et al. A simple and efficient synthesis of trihalomethyl and dihalonitromethyl aryl sulfones
ES2732045T3 (es) Procedimiento de preparación de 3-cloro-2-vinilfenilsulfonatos
CN103664817A (zh) 一种2-丁基-1,2-苯并异噻唑啉-3-酮的合成方法
Ramanathan et al. Cascade annulations of aryldiazonium salts, nitriles and halo-alkynes leading to 3-haloquinolines
TWI413498B (zh) 亞磺醯化吡唑衍生物之方法
BR112014010327B8 (pt) processo para a preparação de compostos
CA2952530A1 (en) Synthesis of halogenated malonic acid diesters and use thereof in the synthesis of 2-halogen-acrylic acid esters
BR112019019589A2 (pt) processo para a preparação de um inibidor quinase estruturado por sulfonamida
WO2016058881A3 (en) Process for the preparation of 1-(3,5-dichlorophenyl)-2,2,2-trifluoroethanone and derivatives thereof
JP2006257042A (ja) ２−フルオロ−６−（トリフルオロメチル）ベンジルブロミドおよび２−フルオロ−６−（トリフルオロメチル）ベンジルアミンの製造方法
CN102786492B (zh) 3-异噻唑啉酮化合物的制备方法
US9334241B2 (en) Process for the preparation of N-substituted pyrazole compounds
JP6994498B2 (ja) ３－アミノ－１－（２，６－二置換フェニル）ピラゾール類を調製する方法
CN107531606A (zh) 2‑卤代苯甲酸类的制造方法
JP5598533B2 (ja) ヨウ素化芳香族化合物の製造方法
CN104672100B (zh) α-羟基芳基乙酰芳胺的合成工艺
CN103772310A (zh) 一种利伐沙班中间体的合成方法
BR112017007751B1 (pt) Processo para a preparação de 5-bromo-1,2,3-triclorobenzeno
CN104130243B (zh) 取代对卤苯基三唑环取代氟化烟酰胺化合物及合成方法