Herbicidal aryldiones incorporating a 5-methoxy-[1,2,5]triazepane ring

Bioorg Med Chem Lett. 2018 Feb 1;28(3):339-343. doi: 10.1016/j.bmcl.2017.12.042. Epub 2017 Dec 20.

Abstract

Novel 2-aryl-cyclic-1,3-diones containing a 5-methoxy-[1,2,5]triazepane unit were explored towards an effective and wheat safe control of grass weeds. Their preparation builds on the ease of synthetic access to 7-membered heterocyclic [1,2,5]triazepane building blocks. Substitution and pattern hopping in the phenyl moiety revealed structure-activity relationships in good agreement with previously disclosed observations amongst the pinoxaden family of acetyl-CoA carboxylase inhibitors. In light of basic physicochemical, enzyme inhibitory and binding site properties, the N-methoxy functionality effectively acts as a bioisostere of the ether group in the seven-membered hydrazine ring.

Keywords: 5-Methoxy-[1,2,5]triazepane; Bioisosteric replacement; Cyclic hydrazine; Grass weed control; Herbicide; Seven-membered heterocycle.

MeSH terms

  • Acetyl-CoA Carboxylase / antagonists & inhibitors*
  • Acetyl-CoA Carboxylase / metabolism
  • Dose-Response Relationship, Drug
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology*
  • Herbicides / chemical synthesis
  • Herbicides / chemistry
  • Herbicides / pharmacology*
  • Ketones / chemical synthesis
  • Ketones / chemistry
  • Ketones / pharmacology*
  • Molecular Structure
  • Structure-Activity Relationship

Substances

  • Enzyme Inhibitors
  • Herbicides
  • Ketones
  • Acetyl-CoA Carboxylase