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Keywords:

  • Chiral pesticides;
  • Plant uptake;
  • Chlordane;
  • Enantioselectivity;
  • Enantiomer toxicities

Abstract

Technical chlordane, a synthetic organic pesticide composed of 147 separate components, some of which exhibit optical activity, was used as an insecticide, herbicide, and termiticide prior to all uses being banned in the United States in 1988. It has been shown that food crops grown in soil treated decades earlier with technical chlordane translocate the weathered chlordane residues from the soil into root and aerial plant tissues. A rigorous analytical method is presented for the simultaneous, quantitative determination of both achiral and chiral components of technical chlordane in soil, plant, and air compartments using chiral gas chromatography interfaced to ion trap mass spectrometry and internal standard calibration. Using this method, we have observed differences in both the absolute and the relative amounts of trans- and cis-chlordane enantiomers and achiral trans-nonachlor between the soil compartment and various plant tissue compartments for several field-grown food crops. Changes in the relative amounts of the (+) and (−) enantiomers of trans- and cis-chlordane indicate enantioselective processes are in effect in the contiguous compartments of soil, plant roots, and aerial plant tissues. The data for zucchini (Cucurbita pepo L.), in particular, show an approximate fivefold enhancement in absolute concentration for total trans-chlordane, an eightfold concentration enhancement for total cis-chlordane, and a 2.5-fold enhancement for trans-nonachlor in the root relative to the soil matrix, the largest enhancements of any crop studied. This is the first comprehensive report of enantioselective processes into and through plant tissues for a variety of field-grown food crops. The selectivity will be related to observed insect toxicities of the enantiomers.