Synthesis, crystal structure and herbicidal activity of mimics of intermediates of the KARI reaction

Pest Manag Sci. 2005 Apr;61(4):407-12. doi: 10.1002/ps.972.

Abstract

Two mimics of the intermediate in the reaction catalyzed by ketol-acid reductoisomerase (KARI) were synthesized. Their structures were established on the basis of elemental analyses, IR, 1H NMR and GC/mass detector. The crystal structure of compound 2 was found to be a substituted dioxane, formed by the condensation of two molecules. The two compounds showed some herbicidal activity on the basis of tests using rape root and barnyard grass growth inhibition. However, the herbicidal effect was weaker in greenhouse tests.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohol Oxidoreductases / antagonists & inhibitors
  • Alcohol Oxidoreductases / metabolism*
  • Brassica / growth & development
  • Herbicides / chemical synthesis
  • Herbicides / chemistry*
  • Herbicides / pharmacology
  • Hydroxybutyrates / chemical synthesis
  • Hydroxybutyrates / chemistry*
  • Hydroxybutyrates / pharmacology
  • Ketol-Acid Reductoisomerase
  • Models, Chemical
  • Models, Molecular
  • Molecular Structure
  • Plant Roots / growth & development
  • Poaceae / growth & development
  • Seedlings / growth & development
  • Substrate Specificity

Substances

  • Herbicides
  • Hydroxybutyrates
  • ethyl 3-hydroxy-2-oxobutanoate
  • ethyl 3-methyl-3-hydroxy-2-oxobutanoate
  • Alcohol Oxidoreductases
  • Ketol-Acid Reductoisomerase