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  • Title: Environmental behavior of the chiral herbicide haloxyfop. 1. Rapid and preferential interconversion of the enantiomers in soil.
    Author: Poiger T, Müller MD, Buser HR, Buerge IJ.
    Journal: J Agric Food Chem; 2015 Mar 18; 63(10):2583-90. PubMed ID: 25742319.
    Abstract:
    Haloxyfop-methyl is a chiral herbicide that was first introduced as racemate and later replaced by "haloxyfop-P-methyl", mainly consisting of the R-enantiomer, which carries the herbicidal activity. We studied the ester cleavage of haloxyfop-methyl and further degradation and chiral inversion of the acid enantiomers in three different soils using enantioselective gas chromatography-mass spectrometry. Our results confirm the rapid ester hydrolysis of haloxyfop-methyl with half-lives of a few hours and indicate that hydrolysis is weakly enantioselective. Further degradation of haloxyfop was slower with half-lives of several days. In all three soils, S-haloxyfop was rapidly converted to R-haloxyfop. In sterile soil, no degradation and no inversion were observed, indicating that both processes are biologically mediated. In soil where 50% of the water had been replaced by deuterium oxide, significant H-D exchange in haloxyfop was observed, pointing to a reaction mechanism involving abstraction of the proton at the chiral center of the molecule.
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