IE41614L - Substituted 2, 2-dimethyl cyclopropane carboxylic acid¹esters. - Google Patents

Substituted 2, 2-dimethyl cyclopropane carboxylic acid¹esters.

Info

Publication number
IE41614L
IE41614L IE169474A IE169474A IE41614L IE 41614 L IE41614 L IE 41614L IE 169474 A IE169474 A IE 169474A IE 169474 A IE169474 A IE 169474A IE 41614 L IE41614 L IE 41614L
Authority
IE
Ireland
Prior art keywords
phenoxybenzyl
cyclopropane ring
furylmethyl
bromine
cyano
Prior art date
Application number
IE169474A
Other versions
IE41614B1 (en
Original Assignee
Nat Res Dev
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
Priority claimed from GB2631674A external-priority patent/GB1448228A/en
Application filed by Nat Res Dev filed Critical Nat Res Dev
Publication of IE41614L publication Critical patent/IE41614L/en
Publication of IE41614B1 publication Critical patent/IE41614B1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40—Radicals substituted by oxygen atoms
    • C07D307/42—Singly bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles

Landscapes

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

Abstract

Insecticides of formula: have particularly good kill and/or knock down properties when R2 and R4 are fluorine, chlorine or bromine and R is 3-phenoxybenzyl or .alpha.-cyano-3-phenoxybenzyl or when at least one of R2 and R3 is fluorine, R can also be 5-benzyl-3-furylmethyl and the ester is in the form of a substantially pure optical isomer with respect to the cyclopropane ring and has ¢R! configuration at C1 of the cyclopropane ring. The esters may be prepared by conventional esterification or by a Wittig synethesis using the desired ester of caronaldehyde and a phosphorane derived from the appropriate dihalo compound. The resolution about the cyclopropane ring can be before or after the esterification or Wittig reaction. The crystalline isomer of the compound wherein R2 and R3 are each bromine and R is .alpha.-cyano-3-phenoxybenzyl has a relative toxicity to houseflies about 23 times greater than that of 5-benzyl-3-furylmethyl (+)-trans chrysanthemate. [CA1045632A]
IE169474A 1973-08-15 1974-08-13 Substituted 2,2-dimethyl cylopropane carboxylic acid estersprocess for their preperation and their use as insecticides IE41614B1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB3953973 1973-08-15
GB4909873 1973-10-22
GB2631674A GB1448228A (en) 1973-10-22 1974-06-13 Substituted 2,2-dimethyl cyclopropane carboxylic acid esters processes for their preparation and their use as insecticides

Publications (2)

Publication Number Publication Date
IE41614L true IE41614L (en) 1975-02-15
IE41614B1 IE41614B1 (en) 1980-02-13

Family

ID=27258509

Family Applications (1)

Application Number Title Priority Date Filing Date
IE169474A IE41614B1 (en) 1973-08-15 1974-08-13 Substituted 2,2-dimethyl cylopropane carboxylic acid estersprocess for their preperation and their use as insecticides

Country Status (7)

Country Link
CA (1) CA1045632A (en)
CH (2) CH608941A5 (en)
DE (1) DE2439177C2 (en)
FR (1) FR2240914A2 (en)
IE (1) IE41614B1 (en)
IT (1) IT1048189B (en)
NL (1) NL178590C (en)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2375161A1 (en) 1976-04-23 1978-07-21 Roussel Uclaf PROCESS FOR TRANSFORMATION OF AN OPTICALLY ACTIVE A-CYANE SECONDARY ALCOHOL CHIRAL ACID ESTER OF STRUCTURE (R) INTO A-CYANE SECONDARY ALCOHOL CHIRAL ACID ESTER OF STRUCTURE (S)
NZ184241A (en) * 1976-06-16 1979-12-11 Ici Ltd A process for the preparation of certain cyano-substituted ester -cyano-3-phenoxybenzyl 3-(2,2-dichl-orovinyl)-2,2-dimethyl-cyclopropane carboxylate insecticidal composition
FR2396006A1 (en) * 1977-06-27 1979-01-26 Roussel Uclaf NEW CYCLOPROPANIC CORE COMPOUNDS, PREPARATION PROCESS AND APPLICATION TO THE PREPARATION OF CYCLOPROPANIC DERIVATIVES WITH DIHALOVINYL CHAIN
CA1123452A (en) * 1977-06-30 1982-05-11 John H. Davies Cyclopropyl carboxylate compounds a process for their manufacture and their use as pesticides
CA1215717A (en) * 1977-09-26 1986-12-23 Samuel B. Soloway Process for converting a stereoisomeric ester into its diastereoisomer
DE2860760D1 (en) * 1977-11-22 1981-09-17 Shell Int Research Method of controlling acarid pests by means of cyclopropane carboxylate esters, the use of such esters as an acaricide, and one of said esters as a novel compound
DE2800922A1 (en) 1978-01-10 1979-07-19 Bayer Ag PROCESS FOR THE SEPARATION OF STEREOISOMER VINYLCYCLOPROPANIC CARBONIC ACIDS
ZA7911B (en) * 1978-01-31 1980-01-30 Roussel Uclaf Optically-active substituted benzyl alcohol and process for preparing it
MD244C2 (en) * 1978-01-31 1995-12-31 Roussel Uclaf, Societe Anonyme Method of preparation of ester of alcohol (S)-a-cyai-3-fenoxybenzol and 1R, cis-2,2-domethyl-3-(2'2'-dibromvinil)-cyclopropan-1-carbonic acid
JPS54163811A (en) * 1978-05-30 1979-12-26 Wellcome Found Harmful organism controlling composition
DK158037C (en) * 1978-06-02 1990-08-13 Shell Int Research METHOD OF COMBATING ACARI USING OXYIMINO-SUBSTITUTED CYCLOPROPANCARBOXYL ACID ESTERS AND Z-ISOMERS OF CERTAIN THESE ESTERS FOR USE BY THE PROCEDURE
FR2428029A1 (en) * 1978-06-06 1980-01-04 Roussel Uclaf ESTERS OF CYCLOPROPANE CARBOXYLIC ACIDS SUBSTITUTED BY A-CYANE ALCOHOL, PROCESS FOR THEIR PREPARATION AND INSECTICIDE OR NEMATICIDE COMPOSITIONS CONTAINING THEM
FR2455024A1 (en) * 1979-04-03 1980-11-21 Roussel Uclaf NEW PROCESS FOR THE SPLITTING OF ACIDS D, L-CIS 2,2-DIMETHYL 3- (2 ', 2'-DIHALOVINYL) CYCLOPROPANE-1-CARBOXYLIC
US4261921A (en) * 1979-06-06 1981-04-14 Fmc Corporation Process for preparation of a crystalline insecticidal pyrethroid enantiomer pair
HU198373B (en) * 1986-01-08 1989-10-30 Chinoin Gyogyszer Es Vegyeszet Artropodicide composition containing trans-cipermetrin isomeres and process for producing the active components
CA1301642C (en) * 1987-03-30 1992-05-26 Howard Bernard Dawson Chemical formulations
CN1157358C (en) * 2000-01-12 2004-07-14 住友化学工业株式会社 Process for synthetizing 2,2-demethyl-3-(1-propenyl) cyclopropane carboxylic ester
WO2022200364A1 (en) 2021-03-25 2022-09-29 Syngenta Crop Protection Ag Insect, acarina and nematode pest control
JP2024516912A (en) 2021-05-14 2024-04-17 シンジェンタ クロップ プロテクション アクチェンゲゼルシャフト Control of insect, acarine and nematode pests
WO2022268815A1 (en) 2021-06-24 2022-12-29 Syngenta Crop Protection Ag Insect, acarina and nematode pest control
WO2022268813A1 (en) 2021-06-24 2022-12-29 Syngenta Crop Protection Ag Insect, acarina and nematode pest control
WO2023105065A1 (en) 2021-12-10 2023-06-15 Syngenta Crop Protection Ag Insect, acarina and nematode pest control
WO2023105064A1 (en) 2021-12-10 2023-06-15 Syngenta Crop Protection Ag Insect, acarina and nematode pest control

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5237046B1 (en) * 1969-11-14 1977-09-20

Also Published As

Publication number Publication date
CH608941A5 (en) 1979-02-15
FR2240914B2 (en) 1982-03-19
NL178590C (en) 1986-04-16
DE2439177A1 (en) 1975-02-27
NL178590B (en) 1985-11-18
FR2240914A2 (en) 1975-03-14
NL7410838A (en) 1975-02-18
DE2439177C2 (en) 1984-02-02
CH611593A5 (en) 1979-06-15
CA1045632A (en) 1979-01-02
IT1048189B (en) 1980-11-20
IE41614B1 (en) 1980-02-13
AU7224974A (en) 1976-02-12

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