Discovery of oxathiapiprolin, a new oomycete fungicide that targets an oxysterol binding protein

Bioorg Med Chem. 2016 Feb 1;24(3):354-61. doi: 10.1016/j.bmc.2015.07.064. Epub 2015 Jul 31.

Abstract

Oxathiapiprolin is the first member of a new class of piperidinyl thiazole isoxazoline fungicides with exceptional activity against plant diseases caused by oomycete pathogens. It acts via inhibition of a novel fungal target-an oxysterol binding protein-resulting in excellent preventative, curative and residual efficacy against key diseases of grapes, potatoes and vegetables. Oxathiapiprolin is being developed globally as DuPont™ Zorvec™ disease control with first registration and sales anticipated in 2015. The discovery, synthesis, optimization and biological efficacy are presented.

Keywords: Crop protection; Disease control; Oomycete fungicide; Oxathiapiprolin; Oxysterol binding protein.

MeSH terms

  • Dose-Response Relationship, Drug
  • Drug Discovery*
  • Hydrocarbons, Fluorinated / chemical synthesis
  • Hydrocarbons, Fluorinated / chemistry
  • Hydrocarbons, Fluorinated / pharmacology*
  • Molecular Structure
  • Oomycetes / drug effects*
  • Oomycetes / metabolism*
  • Oxysterol Binding Proteins
  • Pyrazoles / chemical synthesis
  • Pyrazoles / chemistry
  • Pyrazoles / pharmacology*
  • Receptors, Steroid / antagonists & inhibitors*
  • Structure-Activity Relationship

Substances

  • Hydrocarbons, Fluorinated
  • Pyrazoles
  • Receptors, Steroid
  • Oxysterol Binding Proteins
  • oxathiapiprolin