Hydrolysis and adsorption of cyhalofop-butyl and cyhalofop-acid on soil colloids

J Agric Food Chem. 2008 Jul 9;56(13):5273-7. doi: 10.1021/jf800542b. Epub 2008 Jun 10.

Abstract

A study was undertaken to investigate the stability of cyhalofop-butyl (2 R)-2-[4-(4-cyano-2-fluorophenoxy)phenoxy]butylpropanoate (CyB), an aryloxyphenoxy-propionic herbicide, at different pH values. The hydrolysis of CyB was faster in nonsterile than in sterile water. In sterile medium, CyB degraded only to (2 R)-2-[4-(4-cyano-2-fluorophenoxy)phenoxy]propanoic acid (CyA), whereas in nonsterile water, also the metabolites (2 R)-2-[4-(4-carbamoyl-2-fluorophenoxy)phenoxy]propanoic acid (CyAA) and (2 R)-2-[4-(4-carboxyl-2-fluorophenoxy)phenoxy]propanoic acid (CyD) were detected. The adsorption of CyB onto clays, iron oxide, and dissolved organic matter (DOM), using a batch equilibrium method, was also studied. A lipophilic bond is responsible for CyB adsorption on DOM. CyB was adsorbed on Fe(III)- and Ca-clays through hydrogen bonding between the carbonyl oxygen and water surrounding the exchangeable cations. In the interlayer of K-clay, CyB was hydrolyzed to CyA, which remained adsorbed therein as a monomer. The acid CyA was adsorbed only by the Fe-oxide through complexation. The CyA-Fe-oxide complex was stable and did not undergo degradation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adsorption
  • Aluminum Silicates / chemistry
  • Butanes / chemistry*
  • Chromatography, High Pressure Liquid
  • Clay
  • Colloids / chemistry
  • Environmental Restoration and Remediation / methods*
  • Herbicides / chemistry*
  • Hydrogen-Ion Concentration
  • Hydrolysis
  • Kinetics
  • Nitriles / chemistry*
  • Soil / analysis*
  • Spectroscopy, Fourier Transform Infrared

Substances

  • Aluminum Silicates
  • Butanes
  • Colloids
  • Herbicides
  • Nitriles
  • Soil
  • cyhalofop-butyl
  • Clay