FR2453140A1 - Insecticide and acaricide-phenoxy-benzyl pyrethroid ester prodn. - by reaction of acid chloride with 3-phenoxy-benzaldehyde and alkali cyanide in two=phase system in presence of a phase-transfer catalyst - Google Patents

Insecticide and acaricide-phenoxy-benzyl pyrethroid ester prodn. - by reaction of acid chloride with 3-phenoxy-benzaldehyde and alkali cyanide in two=phase system in presence of a phase-transfer catalyst

Info

Publication number
FR2453140A1
FR2453140A1 FR8007522A FR8007522A FR2453140A1 FR 2453140 A1 FR2453140 A1 FR 2453140A1 FR 8007522 A FR8007522 A FR 8007522A FR 8007522 A FR8007522 A FR 8007522A FR 2453140 A1 FR2453140 A1 FR 2453140A1
Authority
FR
France
Prior art keywords
phenoxy
phase
formula
prodn
acid chloride
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.)
Pending
Application number
FR8007522A
Other languages
French (fr)
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
Application filed by American Cyanamid Co filed Critical American Cyanamid Co
Publication of FR2453140A1 publication Critical patent/FR2453140A1/en
Pending legal-status Critical Current

Links

Classifications

    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N37/00Biocides, 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
    • A01N37/08Biocides, 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 carboxylic groups or thio analogues thereof, directly attached by the carbon atom to a cycloaliphatic ring; Derivatives thereof
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00Carboxylic acid nitriles
    • C07C255/49Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/53Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and hydroxy groups bound to the carbon skeleton

Abstract

For the prodn. of gamma-cyano-3-phenoxybenzyl esters of formula (I), an acid chloride of formula R-CO-Cl (II) is reacted with an equimolar amt or a slight excess of an aldehyde of formula (III) and an equimolar amt or an excess of alkali metal cyanide in the presence of a 2-phase mixt of an insert organic solvent and water and in the presence of 0.1-10 mol% of a phase-transfer catalyst consisting of an organic ammonium salt, an organic phosphonium salt or a crown ether at 20-50 degrees C for the time sufficient for substantially complete reaction. In (I), R is a residue of formula (Ia) or (Ib). (I) are known pyrethroid insecticides and acaricides. They can be used in plant protection, and can also be used against ectropanasites or domesticalted warm-blooded animals. Suprisingly, (I) may be administered orally or parenterally to afford protection against ectoparasitic ticks or insects.
FR8007522A 1979-04-03 1980-04-03 Insecticide and acaricide-phenoxy-benzyl pyrethroid ester prodn. - by reaction of acid chloride with 3-phenoxy-benzaldehyde and alkali cyanide in two=phase system in presence of a phase-transfer catalyst Pending FR2453140A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CA000324757A CA1142953A (en) 1979-04-03 1979-04-03 Process for the preparation of pesticidal esters of certain carboxylic acids using phase transfer catalysts

Publications (1)

Publication Number Publication Date
FR2453140A1 true FR2453140A1 (en) 1980-10-31

Family

ID=4113909

Family Applications (1)

Application Number Title Priority Date Filing Date
FR8007522A Pending FR2453140A1 (en) 1979-04-03 1980-04-03 Insecticide and acaricide-phenoxy-benzyl pyrethroid ester prodn. - by reaction of acid chloride with 3-phenoxy-benzaldehyde and alkali cyanide in two=phase system in presence of a phase-transfer catalyst

Country Status (9)

Country Link
JP (1) JPS55133349A (en)
BR (1) BR8001910A (en)
CA (1) CA1142953A (en)
DE (1) DE3012918A1 (en)
DK (1) DK144580A (en)
ES (1) ES8104793A1 (en)
FR (1) FR2453140A1 (en)
IT (1) IT1127364B (en)
SE (1) SE8002551L (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0303636B1 (en) * 1987-02-13 1992-05-13 Lucky, Ltd. A process for the preparation of pyrethroid type ester compounds

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2342960A1 (en) * 1976-03-01 1977-09-30 Shell Int Research PREPARATION OF BENZYL ESTERS PESTICIDES
EP0000345A1 (en) * 1977-07-06 1979-01-24 Bayer Ag Substituted phenoxybenzyloxycarbonyl derivatives, their preparation and their use as insecticides and acaricides
EP0036774A1 (en) * 1980-03-24 1981-09-30 Sumitomo Chemical Company, Limited Preparation of insecticidal optically active alpha-cyano-3-phenoxybenzyl 2-(4-substituted-phenyl)isovalerates

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2342960A1 (en) * 1976-03-01 1977-09-30 Shell Int Research PREPARATION OF BENZYL ESTERS PESTICIDES
EP0000345A1 (en) * 1977-07-06 1979-01-24 Bayer Ag Substituted phenoxybenzyloxycarbonyl derivatives, their preparation and their use as insecticides and acaricides
EP0036774A1 (en) * 1980-03-24 1981-09-30 Sumitomo Chemical Company, Limited Preparation of insecticidal optically active alpha-cyano-3-phenoxybenzyl 2-(4-substituted-phenyl)isovalerates

Also Published As

Publication number Publication date
DK144580A (en) 1980-10-04
ES490185A0 (en) 1981-05-16
CA1142953A (en) 1983-03-15
BR8001910A (en) 1980-11-25
SE8002551L (en) 1980-10-04
DE3012918A1 (en) 1980-10-23
IT1127364B (en) 1986-05-21
IT8048019A0 (en) 1980-02-27
ES8104793A1 (en) 1981-05-16
JPS55133349A (en) 1980-10-17

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