GB1453655A - Process for preparing cyclopropane-carboxylic acid esters and substituted phenylacetic esters - Google Patents

Process for preparing cyclopropane-carboxylic acid esters and substituted phenylacetic esters

Info

Publication number
GB1453655A
GB1453655A GB3468474A GB3468474A GB1453655A GB 1453655 A GB1453655 A GB 1453655A GB 3468474 A GB3468474 A GB 3468474A GB 3468474 A GB3468474 A GB 3468474A GB 1453655 A GB1453655 A GB 1453655A
Authority
GB
United Kingdom
Prior art keywords
group
carboxylic acid
formula
methyl
viii
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
Application number
GB3468474A
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.)
Sumitomo Chemical Co Ltd
Original Assignee
Sumitomo Chemical 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
Priority claimed from JP8867473A external-priority patent/JPS5111106B2/ja
Priority claimed from JP9498073A external-priority patent/JPS5212697B2/ja
Priority claimed from JP48097063A external-priority patent/JPS5228790B2/ja
Application filed by Sumitomo Chemical Co Ltd filed Critical Sumitomo Chemical Co Ltd
Publication of GB1453655A publication Critical patent/GB1453655A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
    • A01N43/26—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings
    • A01N43/28—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
    • A01N43/30—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3 with two oxygen atoms in positions 1,3, condensed with a carbocyclic ring
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/10—Aromatic or araliphatic carboxylic acids, or thio analogues thereof; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/612—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/62—Halogen-containing esters
    • C07C69/65—Halogen-containing esters of unsaturated acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring

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)

Abstract

1453655 Cyclopropane carboxylic acid esters and substituted phenyl acetic acid esters SUMI. TOMO CHEMICAL CO Ltd 6 Aug 1974 [6 Aug 1973 23 Aug 1973 28 Aug 1973] 34684/74 Heading C2C Organic acid esters of the following general Formula (I) wherein Z is a radical of the formula or R 1 is a hydrogen atom or a methyl group; when R 1 is a hydrogen atom, R 2 is a methyl group, a vinyl group, a 2,2-dichlorovinyl group, a 1- propenyl group, a 2-methyl-1-propenyl group, a 2-carbomethoxy-1-propenyl group, a 2-methoxymethyl - 1 - propenyl group, a 1,3 - butadienyl group, a 2-methyl-1, 3-butadienyl group or a cyclopentylildenemethyl group and, when R 1 is a methyl group, R 2 is also a methyl group; R 3 is an ethyl group or an isopropyl group; R 4 is a hydrogen atom, a C 1 -C 4 alkyl group, a methoxy group, a halogen atom, or a methylenedioxy group are prepared by reacting a quaternary ammonium salt of the following general Formula (VI) wherein X is a halogen atom; and A is an alkylamine, pyridine or an N-alkylaniline, with a carboxylic acid of the following general formula a reactive derivative of the carboxylic acid of the formula (VIII) or a mixture of the carboxylic acid of the formula (VIII) and a reactive derivative of the carboxylic acid of the formula (VIII). The reactive derivatives of the carboxylic acid of Formula (VIII) are preferably the alkali metal salt, the ammonium salt and the alkyl ammonium salt. The compounds have insecticidal properties. The quaternary ammonium salt of Formula VI may be prepared by reacting a 3-phenoxybenzyl halide of the general Formula VII in which X is halogen with an alkyl amine, pyridine or an N-alkyl aniline, e.g. triethylamine, trimethylamine, triethylaniniline, dimethylaniline or pyridine.
GB3468474A 1973-08-06 1974-08-06 Process for preparing cyclopropane-carboxylic acid esters and substituted phenylacetic esters Expired GB1453655A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP8867473A JPS5111106B2 (en) 1973-08-06 1973-08-06
JP9498073A JPS5212697B2 (en) 1973-08-23 1973-08-23
JP48097063A JPS5228790B2 (en) 1973-08-28 1973-08-28

Publications (1)

Publication Number Publication Date
GB1453655A true GB1453655A (en) 1976-10-27

Family

ID=27305880

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3468474A Expired GB1453655A (en) 1973-08-06 1974-08-06 Process for preparing cyclopropane-carboxylic acid esters and substituted phenylacetic esters

Country Status (10)

Country Link
AU (1) AU462570B2 (en)
BR (1) BR7406433D0 (en)
CH (1) CH593232A5 (en)
DE (1) DE2437882C3 (en)
DK (1) DK141934B (en)
FR (1) FR2295009A1 (en)
GB (1) GB1453655A (en)
IL (1) IL45417A (en)
IT (1) IT1047139B (en)
NL (1) NL169996C (en)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IL53946A0 (en) * 1977-03-03 1978-04-30 American Cyanamid Co Phenoxybenzyl esters of benzodioxole acetic acids
US4277617A (en) * 1977-10-27 1981-07-07 Roussel Uclaf Process for the preparation of esters
FR2496652A1 (en) * 1980-12-23 1982-06-25 Roussel Uclaf NOVEL 3-SUBSTITUTED CYCLOPROPANE CARBOXYLIC ACID DERIVATIVES FROM A VINYL CHAIN, PROCESS FOR THEIR PREPARATION AND THEIR USE AS SCENTED AGENTS
CA1301642C (en) * 1987-03-30 1992-05-26 Howard Bernard Dawson Chemical formulations
WO2022200364A1 (en) 2021-03-25 2022-09-29 Syngenta Crop Protection Ag Insect, acarina and nematode pest control
BR112023023835A2 (en) 2021-05-14 2024-01-30 Syngenta Crop Protection Ag COMPOSITIONS FOR SEED TREATMENT
EP4337015A1 (en) 2021-05-14 2024-03-20 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
WO2022268815A1 (en) 2021-06-24 2022-12-29 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
WO2023105065A1 (en) 2021-12-10 2023-06-15 Syngenta Crop Protection Ag Insect, acarina and nematode pest control

Also Published As

Publication number Publication date
NL169996C (en) 1982-09-16
IL45417A (en) 1978-10-31
AU7203074A (en) 1975-06-26
DK141934B (en) 1980-07-21
IT1047139B (en) 1980-09-10
DE2437882C3 (en) 1978-05-11
DE2437882A1 (en) 1975-04-24
DK417174A (en) 1975-04-01
AU462570B2 (en) 1975-06-26
DE2437882B2 (en) 1977-08-25
FR2295009A1 (en) 1976-07-16
NL7410547A (en) 1975-02-10
IL45417A0 (en) 1974-11-29
BR7406433D0 (en) 1975-05-27
CH593232A5 (en) 1977-11-30
DK141934C (en) 1980-12-01
FR2295009B1 (en) 1977-10-14

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PE20 Patent expired after termination of 20 years

Effective date: 19940805