Effect of alcohols and temperature on the direct chiral resolutions of fipronil, isocarbophos and carfentrazone-ethyl

Biomed Chromatogr. 2005 Jul;19(6):454-8. doi: 10.1002/bmc.505.

Abstract

The enantiomeric separations of three pesticides fipronil (asymmetric nitrogen), isocarbophos (asymmetric phosphorus) and carfentrazone-ethyl (asymmetric carbon) were studied on cellulose-tri(3,5-dimethylphenylcarbamate) chiral stationary phase using high-performance liquid chromatography under normal phase. The mobile phase was n-hexane with alcohols including ethanol, n-propanol, iso-propanol, n-butanol and iso-butanol as polar modifiers. The flow rate was 1.0 mL/min with UV detection at 280, 225 and 230 nm for fipronil, isocarbophos and carfentrazone-ethyl respectively. The influence of the modifiers and their volume content and temperature from 0 to 50 degrees C on the separations was investigated. The chiral stationary phase showed excellent stereoselectivity for the two enantiomers of fipronil and isocarbophos and certain chiral recognition for carfentrazone-ethyl. Iso-propanol was more suitable for the chiral separation of isocarbophos and carfentrazone-ethyl, and iso-butanol was better for fipronil. The resolutions increased with the decreasing modifier content and temperature for all the three chiral pesticides.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemistry*
  • Cellulose / analogs & derivatives
  • Chromatography, High Pressure Liquid / methods*
  • Malathion / analogs & derivatives*
  • Malathion / isolation & purification*
  • Pesticides / isolation & purification*
  • Phenylcarbamates
  • Pyrazoles / isolation & purification*
  • Temperature
  • Triazoles / isolation & purification*

Substances

  • Alcohols
  • Pesticides
  • Phenylcarbamates
  • Pyrazoles
  • Triazoles
  • cellulose tris-3,5-dimethylphenyl-carbamate
  • carfentrazone-ethyl
  • Cellulose
  • fipronil
  • Malathion