Quarternary α-cyanobenzylsulfonamides: A new subclass of CAA fungicides with excellent anti-Oomycetes activity

Bioorg Med Chem. 2021 Jan 15:30:115965. doi: 10.1016/j.bmc.2020.115965. Epub 2020 Dec 26.

Abstract

A bioisosteric carboxamide - sulfonamide replacement explored during the optimization of an insecticide lead compound led to the surprising discovery of a formerly unknown subclass of the Carboxylic Acid Amide (CAA) fungicides, which is the very first CAA fungicide group without a carboxamide function. In this paper we present invention pathway, racemic and stereoselective synthesis routes, structure-activity relationship studies as well as resistance profile of this novel family of fungicides.

Keywords: Carboxylic acid amide fungicides; Crop protection; Mandipropamid; Oomycetes diseases; Sulfonamide.

MeSH terms

  • Dose-Response Relationship, Drug
  • Drug Resistance, Fungal / drug effects
  • Fungicides, Industrial / chemical synthesis
  • Fungicides, Industrial / chemistry
  • Fungicides, Industrial / pharmacology*
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Nitriles / chemical synthesis
  • Nitriles / chemistry
  • Nitriles / pharmacology*
  • Oomycetes / drug effects*
  • Plant Diseases / prevention & control
  • Stereoisomerism
  • Structure-Activity Relationship
  • Sulfonamides / chemical synthesis
  • Sulfonamides / chemistry
  • Sulfonamides / pharmacology*

Substances

  • Fungicides, Industrial
  • Nitriles
  • Sulfonamides