Design, synthesis, and insecticidal evaluation of new benzoylureas containing amide and sulfonate groups based on the sulfonylurea receptor protein binding site for diflubenzuron and glibenclamide

J Agric Food Chem. 2013 Jan 23;61(3):517-22. doi: 10.1021/jf304468b. Epub 2013 Jan 10.

Abstract

On the basis of the sulfonylurea receptor (SUR) protein binding site for diflubenzuron and glibenclamide, 15 new benzoylphenylureas containing amide and sulfonate groups were designed and synthesized. Their structures were characterized by (1)H nuclear magnetic resonance (NMR) and elemental analysis [or high-resolution mass spectrometry (HRMS)]. The larvicidal activities of the new compounds against oriental armyworm and diamondback moth were evaluated. Compound II-3 showed nearly the same level of insecticidal activity against oriental armyworm as commercial insecticide flucycloxuron and, thus, emerged as a new lead compound for the development of new benzoylurea insecticides.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Diflubenzuron / chemical synthesis*
  • Glyburide / chemical synthesis*
  • Insecticides / chemical synthesis*
  • Larva
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Moths*
  • Phenylurea Compounds / chemical synthesis
  • Phenylurea Compounds / chemistry
  • Protein Binding
  • Structure-Activity Relationship
  • Sulfonylurea Receptors / genetics
  • Sulfonylurea Receptors / metabolism

Substances

  • Insecticides
  • Phenylurea Compounds
  • Sulfonylurea Receptors
  • Diflubenzuron
  • flucycloxuron
  • Glyburide