Isoflucypram, the first representative of a new succinate dehydrogenase inhibitor fungicide subclass: Its chemical discovery and unusual binding mode

Pest Manag Sci. 2020 Oct;76(10):3340-3347. doi: 10.1002/ps.5951. Epub 2020 Jul 2.

Abstract

Succinate dehydrogenase inhibitors (SDHIs) have played a crucial role in disease control to protect cereals as well as fruit and vegetables for more than a decade. Isoflucypram, the first representative of a newly installed subclass of SDHIs inside the Fungicide Resistance Action Committee (FRAC) family of complex II inhibitors, offers unparalleled long-lasting efficacy against major foliar diseases in cereals. Herein we report the chemical optimization from early discovery towards isoflucypram and the first hypothesis of its altered binding mode in the ubiquinone binding site of succinate dehydrogenase. © 2020 The Authors. Pest Management Science published by John Wiley & Sons Ltd on behalf of Society of Chemical Industry.

Keywords: ISY; N-cyclopropyl-N-benzyl-pyrazole carboxamide; SDHI; isoflucypram; ubiquinone binding site.

Publication types

  • Review

MeSH terms

  • Drug Resistance, Fungal
  • Fungicides, Industrial
  • Plant Diseases
  • Succinate Dehydrogenase / antagonists & inhibitors*
  • Succinic Acid

Substances

  • Fungicides, Industrial
  • Succinic Acid
  • Succinate Dehydrogenase