Conversion of pyrethroid isomers to more active species

C - Chemistry – Metallurgy – 07 – C

Patent

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260/496.6

C07C 253/30 (2006.01) C07C 255/39 (2006.01) C07C 255/53 (2006.01)

Patent

CA 1314559

ABSTRACT: Crystallizable pyrethroid isomers or enantiomer pairs are converted to more pesticidally active isomers by contacting a hydrocarbon slurry of the starting isomers with a base and a catalyst, the catalyst being substantially soluble in the slurry and selected from a quaternary ammonium compound, a quaternary phosphonium compound and a crown ether, agitating the slurry while maintaining a temperature effective for conversion, and recovering the resulting isomers. The tendency to form benzoin ester by-product is reduced by including in the slurry a weak base, an aldehyde scavenger such as a metabisulfite, and/or a tetraalkyl(C1-C5)ammonium halide catalyst dissolved in an aprotic solvent such as an organic nitrile. The process typically is effective for enriching cypermethrin, cyfluthrin and (cyano)(3-phen- oxyphenyl)methyl 3-(2,2-dibromoethenyl)-2,2-dimeth- ylcyclopropanecarboxylate in the more active species.

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