GB2000764A - Halogenated cyclopropane carboxylic acid esters - Google Patents

Halogenated cyclopropane carboxylic acid esters

Info

Publication number
GB2000764A
GB2000764A GB7827485A GB7827485A GB2000764A GB 2000764 A GB2000764 A GB 2000764A GB 7827485 A GB7827485 A GB 7827485A GB 7827485 A GB7827485 A GB 7827485A GB 2000764 A GB2000764 A GB 2000764A
Authority
GB
United Kingdom
Prior art keywords
bromine
chlorine
fluorine
carboxylic acid
acid esters
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.)
Granted
Application number
GB7827485A
Other versions
GB2000764B (en
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries 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 Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Publication of GB2000764A publication Critical patent/GB2000764A/en
Application granted granted Critical
Publication of GB2000764B publication Critical patent/GB2000764B/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C61/16—Unsaturated compounds
    • C07C61/40—Unsaturated compounds containing halogen
    • 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
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Insecticidal compounds have the general formula: <IMAGE> wherein one of R<1> and R<2> is a haloalkyl group containing one or two carbon atoms and the other is a halogen atom and in which R is a phenoxybenzyloxy group optionally substituted in the alpha -position by a cyano or ethynyl group. A typical example is (+/-)- alpha -cyano-3-phenoxybenzyl (+/-)-cis/trans-3-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethy lcyclopropane carboxylate. The compounds may be prepared from the corresponding compounds where R is hydroxy, halo or alkoxy, which are also novel, which, in turn, may be prepared by reacting a novel compound of the formula: <IMAGE> wherein one of R<1> and R<2> represents a group of the formula: W-(CF2)<m>- where W is hydrogen, fluorine or chlorine and m is 1 or 2, and the other of R<1> and R<2> is fluorine, chlorine or bromine; Q is (C1-C6) alkoxy, and W' and W'' are independently fluorine, chlorine or bromine, provided that W' is bromine when R<2> is bromine, with at least two equivalents of a base.
GB7827485A 1977-03-23 1978-06-21 Halogenated esters Expired GB2000764B (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB5134077 1977-03-23
GB5134177 1977-09-02
GB812978 1978-03-01

Publications (2)

Publication Number Publication Date
GB2000764A true GB2000764A (en) 1979-01-17
GB2000764B GB2000764B (en) 1982-04-28

Family

ID=27255145

Family Applications (1)

Application Number Title Priority Date Filing Date
GB7827485A Expired GB2000764B (en) 1977-03-23 1978-06-21 Halogenated esters

Country Status (3)

Country Link
GB (1) GB2000764B (en)
HK (1) HK55085A (en)
KE (1) KE3526D (en)

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2348194A1 (en) * 1976-04-15 1977-11-10 Ici Ltd PROCESS FOR THE PRODUCTION OF ESTERS OF A M-PHENOXYBENZYL ALCOHOL AND OF A HIGHER CARBOXYLIC ACID
EP0009709A1 (en) * 1978-09-29 1980-04-16 Bayer Ag Fluoro-alkenyl-substituted cyclopropane carboxylic acid esters (I), processes for their production, intermediates obtained thereby and their preparation, compositions containing the esters (I) and the use of the esters (I) in combating insects and/or spiders
EP0010879A1 (en) * 1978-10-27 1980-05-14 Imperial Chemical Industries Plc Halogenated esters of cyclopropane acids, their preparation, compositions and use as pesticides
US4254052A (en) 1979-09-27 1981-03-03 Fmc Corporation Preparation of esters
US4254050A (en) 1979-09-27 1981-03-03 Fmc Corporation Preparation of esters
US4254051A (en) 1979-09-27 1981-03-03 Fmc Corporation Preparation of esters
EP0026437A1 (en) * 1979-10-02 1981-04-08 Bayer Ag 3-(2,3-dichloro-3,3-difluoro-prop-1-en-1-yl)2,2 dimethyl cyclopropionic acid fluorobenzyl esters, process for their manufacture and their use in pesticides
US4299776A (en) 1979-12-13 1981-11-10 Fmc Corporation Preparation of esters
EP0043143A2 (en) * 1980-07-02 1982-01-06 Montedison S.p.A. Process for stereoselectively synthetizing cyclopropane carboxylates as intermediates for pyrethroids
US4322535A (en) 1980-06-13 1982-03-30 Fmc Corporation Preparation of esters
US4322534A (en) 1980-06-06 1982-03-30 Fmc Corporation Preparation of esters
US4323685A (en) 1980-06-13 1982-04-06 Fmc Corporation Preparation of esters
WO1983000485A1 (en) * 1981-08-06 1983-02-17 Fmc Corp Intermediates and process for insecticidal synthetic pyrethroids
EP0106469A1 (en) * 1982-10-11 1984-04-25 Imperial Chemical Industries Plc Insecticidal product and preparation thereof
US4510160A (en) * 1982-10-11 1985-04-09 Imperial Chemical Industries Plc Insecticidal product and preparation thereof
US4510098A (en) * 1983-03-28 1985-04-09 Imperial Chemical Industries Plc Insecticidal product
US4551281A (en) * 1978-10-31 1985-11-05 Imperial Chemical Industries Plc Process for the preparation of cyclopropane carboxylic acid esters
WO1994027951A1 (en) * 1993-05-28 1994-12-08 Zeneca Limited Preparation of cyclopropane esters
US5986130A (en) * 1995-07-21 1999-11-16 Cheminova Agro A/S Process for the preparation of cyclopropane carboxylic acids and intermediates therefor
WO2004056752A1 (en) * 2002-12-20 2004-07-08 Syngenta Limited Production process of gamma-cyhalothrin

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109111373A (en) * 2018-10-09 2019-01-01 南通天泽化工有限公司 A kind of preparation method of Cyhalothrin

Cited By (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2348194A1 (en) * 1976-04-15 1977-11-10 Ici Ltd PROCESS FOR THE PRODUCTION OF ESTERS OF A M-PHENOXYBENZYL ALCOHOL AND OF A HIGHER CARBOXYLIC ACID
EP0009709A1 (en) * 1978-09-29 1980-04-16 Bayer Ag Fluoro-alkenyl-substituted cyclopropane carboxylic acid esters (I), processes for their production, intermediates obtained thereby and their preparation, compositions containing the esters (I) and the use of the esters (I) in combating insects and/or spiders
EP0010879A1 (en) * 1978-10-27 1980-05-14 Imperial Chemical Industries Plc Halogenated esters of cyclopropane acids, their preparation, compositions and use as pesticides
US4551281A (en) * 1978-10-31 1985-11-05 Imperial Chemical Industries Plc Process for the preparation of cyclopropane carboxylic acid esters
US4254052A (en) 1979-09-27 1981-03-03 Fmc Corporation Preparation of esters
US4254050A (en) 1979-09-27 1981-03-03 Fmc Corporation Preparation of esters
US4254051A (en) 1979-09-27 1981-03-03 Fmc Corporation Preparation of esters
EP0026437A1 (en) * 1979-10-02 1981-04-08 Bayer Ag 3-(2,3-dichloro-3,3-difluoro-prop-1-en-1-yl)2,2 dimethyl cyclopropionic acid fluorobenzyl esters, process for their manufacture and their use in pesticides
US4299776A (en) 1979-12-13 1981-11-10 Fmc Corporation Preparation of esters
US4322534A (en) 1980-06-06 1982-03-30 Fmc Corporation Preparation of esters
US4322535A (en) 1980-06-13 1982-03-30 Fmc Corporation Preparation of esters
US4323685A (en) 1980-06-13 1982-04-06 Fmc Corporation Preparation of esters
EP0043143A3 (en) * 1980-07-02 1982-10-13 Montedison S.P.A. Process for stereoselectively synthetizing cyclopropane carboxylates as intermediates for pyrethroids
EP0043143A2 (en) * 1980-07-02 1982-01-06 Montedison S.p.A. Process for stereoselectively synthetizing cyclopropane carboxylates as intermediates for pyrethroids
WO1983000485A1 (en) * 1981-08-06 1983-02-17 Fmc Corp Intermediates and process for insecticidal synthetic pyrethroids
EP0106469A1 (en) * 1982-10-11 1984-04-25 Imperial Chemical Industries Plc Insecticidal product and preparation thereof
US4510160A (en) * 1982-10-11 1985-04-09 Imperial Chemical Industries Plc Insecticidal product and preparation thereof
US4510098A (en) * 1983-03-28 1985-04-09 Imperial Chemical Industries Plc Insecticidal product
US5670697A (en) * 1993-05-28 1997-09-23 Zeneca Limited Preparation of cyclopropane esters
WO1994027951A1 (en) * 1993-05-28 1994-12-08 Zeneca Limited Preparation of cyclopropane esters
AU696683B2 (en) * 1993-05-28 1998-09-17 Zeneca Limited Preparation of cyclopropane esters
CN1065235C (en) * 1993-05-28 2001-05-02 曾尼卡有限公司 Preparation of cyclopropane esters
US5986130A (en) * 1995-07-21 1999-11-16 Cheminova Agro A/S Process for the preparation of cyclopropane carboxylic acids and intermediates therefor
WO2004056752A1 (en) * 2002-12-20 2004-07-08 Syngenta Limited Production process of gamma-cyhalothrin
EP1578720A1 (en) 2002-12-20 2005-09-28 Syngenta Limited Production process of gamma-cyhalothrin
JP2006510704A (en) * 2002-12-20 2006-03-30 シンジェンタ リミテッド Method for producing gamma-cyhalothrin
US7468453B2 (en) 2002-12-20 2008-12-23 Syngenta Limited Production process of gamma-cyhalothrin

Also Published As

Publication number Publication date
HK55085A (en) 1985-07-26
KE3526D (en) 1985-06-07
GB2000764B (en) 1982-04-28

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Legal Events

Date Code Title Description
732E Amendments to the register in respect of changes of name or changes affecting rights (sect. 32/1977)
CTFF Supplementary protection certificate filed

Free format text: SPC/GB93/138, 930630

CTFG Supplementary protection certificate granted

Free format text: SPC/GB93/138 940225, EXPIRES:20010213

CTFF Supplementary protection certificate filed

Free format text: SPC/GB97/039, 19970722

CTFG Supplementary protection certificate granted

Free format text: SPC/GB97/039, 19980521, EXPIRES: 20001107

CTFE Supplementary protection certificate entered into force

Free format text: SPC/GB97/039, 19980621, EXPIRES: 20001107

PE20 Patent expired after termination of 20 years

Effective date: 19980620

SPCE Supplementary protection certificate expired

Free format text: SPC/GB97/039: 20001107

SPCE Supplementary protection certificate expired

Free format text: SPC/GB93/138, 20010213