Enantioselectivity in degradation and transformation of quizalofop-ethyl in soils

Chirality. 2012 Jul;24(7):552-7. doi: 10.1002/chir.22053. Epub 2012 May 8.

Abstract

The enantioselective degradation of quizalofop-ethyl and its metabolite quizalofop-acid in two soils, a Wuhan acidic soil and a Baoding alkaline soil, was investigated. The dissipation of quizalofop-ethyl consisted of two phases, a rapidly deceasing first phase that lasted 1 day and a slowly decreasing second phase that extended till the end of the incubation. It is shown that S-quizalofop-ethyl degraded slightly faster than R-quizalofop-ethyl in the two soils. Further incubation of enantiopure enaniomers showed that quizalofop-ethyl was configurationally stable in soil. Quizalofop-acid was produced quickly, and its amount reached a maximum at 1-6 days time and then decreased slowly with half-lives ranging from 11 to 21 days. The results also showed that quizalofop-acid degraded faster in the acidic Wuhan soil than in the alkaline Baoding soil. At last, significant enantiomerization from S-quizalofop-acid to R-quizalofop-acid was observed, and the enantiomerization was fast, resulting in residues enriched with R-quizalofop-acid whatever racemic quizalofop-ethyl or pure enantiomers were initially applied in the soils.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Hydrogen-Ion Concentration
  • Propionates / chemistry*
  • Propionates / metabolism
  • Quinoxalines / chemistry*
  • Quinoxalines / metabolism
  • Soil / chemistry*
  • Stereoisomerism
  • Substrate Specificity

Substances

  • Propionates
  • Quinoxalines
  • Soil
  • quizalofop-ethyl