Chiral separation of metalaxyl and benalaxyl fungicides by electrokinetic chromatography and determination of enantiomeric impurities

J Chromatogr A. 2011 Jul 29;1218(30):4877-85. doi: 10.1016/j.chroma.2010.12.116. Epub 2011 Jan 5.

Abstract

The enantiomers of two acylamine fungicides (metalaxyl and benalaxyl) were separated by EKC using CDs as chiral selectors. The use of 15 mM succinyl-γ-CD for metalaxyl and 5 mM succinyl-β-CD for benalaxyl dissolved in a 50 mM 2-morpholinoethanesulfonic acid buffer (pH 6.5), enabled the chiral separation of metalaxyl enantiomers in 11.5 min with a resolution of 3.1 and the enantiomeric separation of benalaxyl in 7.5 min with a resolution close to 15. Under these conditions, the two enantiomers of each of the chiral compound studied were also separated from folpet, very commonly present in fungicide formulations containing metalaxyl or benalaxyl. The analytical characteristics of the two developed methods were studied in terms of precision, linearity, selectivity, limits of detection (LODs) and limits of quantitation (LOQs) showing their suitability for the determination of these compounds in commercial agrochemical formulations. Finally, the development of an in-capillary preconcentration strategy allowed the detection of enantiomeric impurities up to 1.2% in commercial products labeled as enantiomerically pure in metalaxyl-M.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alanine / analogs & derivatives*
  • Alanine / analysis
  • Alanine / chemistry
  • Alanine / isolation & purification
  • Analysis of Variance
  • Chromatography, Micellar Electrokinetic Capillary / methods*
  • Drug Contamination*
  • Fungicides, Industrial / analysis
  • Fungicides, Industrial / chemistry*
  • Fungicides, Industrial / isolation & purification
  • Reproducibility of Results
  • Sensitivity and Specificity
  • Stereoisomerism

Substances

  • Fungicides, Industrial
  • metalaxyl
  • benalaxyl
  • Alanine