Fmc Corporation

Ronald Eugene Montgomery

Ernest L Plummer

Anthony J Martinez

Leland A Smeltz

Harry Hobart Incho

This invention relates to a process for preparing certain isomers of 2,2-dimethyl-3-(2,2-disubstitutedvinyl)cyclopropanecarboxylic acid or derivatives thereof. More specifically it relates to the epimerization of the 1S cyclopropanecarboxylic acid and its derivatives into the corresponding 1R isomers.

1S to 1R Epimerizations of pyrethroid intermediates

A novel N,N,N-trimethyl-[1,1'-biphenyl]-2-methanaminium compound is subjected to a rearrangement reaction to give a 3-dimethylaminomethyl-2-methyl-[1,1'-biphenyl] compound which is then converted to the corresponding 3-halomethyl-2-methyl-[1,1'-biphenyl] compound. The halomethyl compound is an intermediate for pyrethroid and related insecticides having the alcohol moiety derived from a 2-methyl-[1,1'-biphenyl]-3-methanol.

Pyrethroid intermediates and process

Synergistic insecticidal combinations of esters of certain cyclopropanecarboxylic acids, e.g. pyrethrins, allethrin, and related compounds, with mono(alkyl and alkenyl) mono-.omega.-alkynyl aryl- and aralkylphosphonates are described. The preparation and properties of representative members of this new class of synergistic phosphonates are described, and test results of their synergistic combinations with representative cyclopropanecarboxylates are reported.

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Middleport, NY, United States of America

Ronald Eugene Montgomery