Comparative study of the selective degradations of two enantiomers in the racemate and an enriched concentration of indoxacarb in soils

J Agric Food Chem. 2014 Sep 17;62(37):9066-72. doi: 10.1021/jf5018803. Epub 2014 Sep 9.

Abstract

In this study, selective degradations of the two enantiomers of indoxacarb in the concentrate (2.33S/1R) and racemate (1S/1R) are examined. The absolute configurations of indoxacarb enantiomers were determined using X-ray diffraction. The results showed that in two alkaline soils, the S-(+)-indoxacarb was preferentially degraded in both the concentrate and racemate. In one acid soil, the two enantiomers degraded no-selectivity. In another acid soil and one neutral soil, the R-(-)-indoxacarb was preferentially degraded in both the concentrate and racemate. Indoxacarb enantiomers were configurationally stable in the five soils, and no interconversion was observed during the incubation. Because no significant difference in degradation was observed after samples were sterilized, the observed enantioselectivity may be attributed primarily to microbial activity in soils. The results indicate that the selective degradation behavior was the same for both formulations that were tested.

Keywords: absolute configuration; enantiomers; enantioselective degradation; indoxacarb; soil.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Crystallization
  • Hydrogen-Ion Concentration
  • Insecticides*
  • Molecular Structure
  • Oxazines / analysis*
  • Oxazines / chemistry*
  • Oxazines / metabolism
  • Soil / chemistry*
  • Soil Microbiology
  • Stereoisomerism
  • X-Ray Diffraction

Substances

  • Insecticides
  • Oxazines
  • Soil
  • indoxacarb