GB2017688A - Novel m-phenoxybenzyl ester derivative useful as insecticidal and acaracidal agent - Google Patents

Novel m-phenoxybenzyl ester derivative useful as insecticidal and acaracidal agent

Info

Publication number
GB2017688A
GB2017688A GB7909542A GB7909542A GB2017688A GB 2017688 A GB2017688 A GB 2017688A GB 7909542 A GB7909542 A GB 7909542A GB 7909542 A GB7909542 A GB 7909542A GB 2017688 A GB2017688 A GB 2017688A
Authority
GB
United Kingdom
Prior art keywords
novel
acaracidal
insecticidal
agent
alpha
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
GB7909542A
Other versions
GB2017688B (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.)
Wyeth Holdings LLC
Original Assignee
American Cyanamid Co
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 US05/890,721 external-priority patent/US4178460A/en
Priority claimed from US05/890,568 external-priority patent/US4199595A/en
Application filed by American Cyanamid Co filed Critical American Cyanamid Co
Publication of GB2017688A publication Critical patent/GB2017688A/en
Application granted granted Critical
Publication of GB2017688B publication Critical patent/GB2017688B/en
Expired legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • 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
    • 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
    • A01N37/34—Nitriles
    • 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
    • A01N37/36—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 containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • A01N37/38—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 containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
    • 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
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/10—Sulfones; Sulfoxides
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
    • C07C255/38—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
    • C07C47/575—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/08—Preparation of carboxylic acids or their salts, halides or anhydrides from nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/363—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/58—Preparation of carboxylic acid halides
    • C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
    • 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
    • C07C69/612—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
    • C07C69/614—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 of phenylacetic acid

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Plant Pathology (AREA)
  • Agronomy & Crop Science (AREA)
  • Environmental Sciences (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Public Health (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

This invention provides a novel m- phenoxybenzyl ester derivative which is useful as an insecticidal and acaracidal agent. The novel compound is (+/-)- alpha -cyano-m-phenoxybenzyl (+)- alpha -isopropyl-4- difluoromethoxyphenylacetate which may be obtained by reaction of a (+)- alpha -isopropyl-4-difluoromethoxyacetyl halide with (+/-)- alpha -cyano-m- phenoxybenzyl alcohol. The structure of the novel compound is represented by the formula: <IMAGE> The novel compound exhibits outstanding activity as a contact and stomach poison for ixodide ticks and for a wide variety of insects.
GB7909542A 1978-03-20 1979-03-19 M-phenoxybenzyl ester derivative useful as insecticidal and acaricidal agent Expired GB2017688B (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US05/890,721 US4178460A (en) 1976-10-01 1978-03-20 2-Haloalkyl(oxy-, thio-, sulfinyl-, or sulfonyl)-phenylalkanoic acids
US05/890,568 US4199595A (en) 1976-10-01 1978-03-20 M-phenoxybenzyl and α-cyano-M-phenoxybenzyl esters of 2-haloalkyl (oxy-, thio-, sulfinyl-, or sulfonyl)phenylalkanoic acids

Publications (2)

Publication Number Publication Date
GB2017688A true GB2017688A (en) 1979-10-10
GB2017688B GB2017688B (en) 1982-08-18

Family

ID=27128953

Family Applications (1)

Application Number Title Priority Date Filing Date
GB7909542A Expired GB2017688B (en) 1978-03-20 1979-03-19 M-phenoxybenzyl ester derivative useful as insecticidal and acaricidal agent

Country Status (17)

Country Link
JP (1) JPS54135742A (en)
AR (1) AR228014A1 (en)
AT (1) AT367965B (en)
AU (2) AU528525B2 (en)
BR (1) BR7901697A (en)
CH (2) CH640513A5 (en)
DD (5) DD150455A6 (en)
DK (1) DK112679A (en)
ES (2) ES8105253A1 (en)
GB (1) GB2017688B (en)
GR (1) GR74446B (en)
HU (1) HU182016B (en)
NL (1) NL7902153A (en)
NZ (1) NZ189915A (en)
PL (1) PL123011B1 (en)
RO (1) RO79551A (en)
SE (1) SE444313B (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2470764A1 (en) * 1979-11-28 1981-06-12 American Cyanamid Co (-) - A-ISOPROPYL-4-DIFLUOROMETHOXYPHENYLACETATE OF (-) - A-CYANO-M-PHENOXYBENZYL AND ITS USE AS INSECTICIDE
EP0101570A1 (en) * 1982-08-23 1984-02-29 American Cyanamid Company Method for the resolution of racemic 2-CP-difluoromethoxy phenyl)-3-methylbutyric acid

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2837524A1 (en) * 1978-08-28 1980-03-20 Bayer Ag Phenylacetic acid ester derivs. from pyrethroid alcohol(s) - useful as insecticides and acaricides, and new intermediates
JPS56133253A (en) * 1980-03-24 1981-10-19 Sumitomo Chem Co Ltd Optical isomer of cyanohydrin ester, its production and insecticide and acaricide containing the same as effective ingredient
JPS56139445A (en) * 1980-04-02 1981-10-30 Sumitomo Chem Co Ltd Stereoisomer of cyanohydrin ester, its production and insecticide, acaricide containing the same as active principle
JPS5793948A (en) * 1980-12-02 1982-06-11 Sumitomo Chem Co Ltd Preparation of stereoisomer mixture of higher active phenylacetic ester derivative
DE3103325A1 (en) * 1981-01-31 1982-08-26 Bayer Ag, 5090 Leverkusen 4-FLUOR-3-HALOPHENOXY-BENZYL ESTER, METHOD FOR THE PRODUCTION AND USE THEREOF IN PEST CONTROL, AND NEW INTERMEDIATE PRODUCTS AND METHOD FOR THE PRODUCTION THEREOF
FR2512815B1 (en) * 1981-04-16 1989-04-14 Roussel Uclaf NOVEL DERIVATIVES OF CYCLOPROPANE CARBOXYLIC ACID, THEIR PREPARATION METHOD, THEIR APPLICATION TO THE CONTROL OF PESTS

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5133612B2 (en) * 1973-04-19 1976-09-21 Sumitomo Chemical Co
IL52973A (en) * 1976-10-01 1983-10-31 American Cyanamid Co Alpha-(haloalkoxy and haloalkyl-thiophenyl)alkanoic acid ester derivatives,their preparation and insecticidal and acaricidal compositions containing them

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2470764A1 (en) * 1979-11-28 1981-06-12 American Cyanamid Co (-) - A-ISOPROPYL-4-DIFLUOROMETHOXYPHENYLACETATE OF (-) - A-CYANO-M-PHENOXYBENZYL AND ITS USE AS INSECTICIDE
EP0101570A1 (en) * 1982-08-23 1984-02-29 American Cyanamid Company Method for the resolution of racemic 2-CP-difluoromethoxy phenyl)-3-methylbutyric acid

Also Published As

Publication number Publication date
ES478787A0 (en) 1981-05-16
DD143601A5 (en) 1980-09-03
AU4525179A (en) 1979-09-27
JPS54135742A (en) 1979-10-22
SE444313B (en) 1986-04-07
RO79551A (en) 1982-08-17
DD150455A6 (en) 1981-09-02
ATA204979A (en) 1982-01-15
PL123011B1 (en) 1982-09-30
JPS6362507B2 (en) 1988-12-02
ES8303283A2 (en) 1983-02-01
PL214234A3 (en) 1980-08-25
AU528525B2 (en) 1983-05-05
DD149601A6 (en) 1981-07-22
CH641638A5 (en) 1984-03-15
AT367965B (en) 1982-08-25
BR7901697A (en) 1979-10-16
DD154535A5 (en) 1982-03-31
NZ189915A (en) 1981-04-24
GR74446B (en) 1984-06-28
AU4524279A (en) 1979-09-27
CH640513A5 (en) 1984-01-13
DD152539A5 (en) 1981-12-02
AU525146B2 (en) 1982-10-21
ES478785A0 (en) 1983-02-01
SE7902467L (en) 1979-11-19
HU182016B (en) 1983-12-28
DK112679A (en) 1979-09-21
GB2017688B (en) 1982-08-18
ES8105253A1 (en) 1981-05-16
AR228014A1 (en) 1983-01-14
NL7902153A (en) 1979-09-24

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PCNP Patent ceased through non-payment of renewal fee