Dissipation of the Herbicide Benzobicyclon Hydrolysate in a Model California Rice Field Soil

J Agric Food Chem. 2017 Oct 25;65(42):9200-9207. doi: 10.1021/acs.jafc.7b03679. Epub 2017 Oct 11.

Abstract

The herbicide benzobicyclon (BZB; 3-(2-chloro-4-(methylsulfonyl)benzoyl)-2-phenylthiobicyclo[3.2.1]oct-2-en-4-one) has recently been approved for use on California rice fields by the United States Environmental Protection Agency (U.S. EPA). Hydrolysis of BZB rapidly forms the active compound, benzobicyclon hydrolysate (BH), whose fate is currently not well understood. A model California rice soil was used to determine BH soil dissipation. The pKa and aqueous solubility were also determined, as experimental values are not currently available. Sorption data indicate BH does not bind tightly, or irreversibly, with this soil. Flooding resulted in decreased BH loss, indicating anaerobic microbes are less likely to transform BH compared to aerobic microorganisms. Temperature increased dissipation, while autoclaving decreased BH loss. Overall, dissipation was slow regardless of treatment. Further investigation is needed to elucidate the exact routes of loss in soil, though BH is expected to dissipate slowly in flooded rice field soil.

Keywords: benzobicyclon; benzobicyclon hydrolysate; herbicide; pesticide; rice; soil dissipation.

MeSH terms

  • Bacteria / metabolism
  • Biodegradation, Environmental
  • Bridged Bicyclo Compounds / chemistry*
  • Bridged Bicyclo Compounds / metabolism
  • California
  • Herbicides / chemistry*
  • Herbicides / metabolism
  • Kinetics
  • Molecular Structure
  • Oryza / growth & development*
  • Soil / chemistry*
  • Soil Microbiology
  • Soil Pollutants / chemistry
  • Soil Pollutants / metabolism
  • Sulfones / chemistry*
  • Sulfones / metabolism

Substances

  • Bridged Bicyclo Compounds
  • Herbicides
  • Soil
  • Soil Pollutants
  • Sulfones
  • benzobicyclon