Synthesis and herbicidal activity of 2-cyano-3-(2-chlorothiazol-5-yl)methylaminoacrylates

J Agric Food Chem. 2004 Apr 7;52(7):1918-22. doi: 10.1021/jf035312a.

Abstract

A series of 2-cyano-3-(2-chlorothiazol-5-yl)methylaminoacrylates were synthesized as herbicidal inhibitors of PSII electron transport. All of these compounds exhibited good herbicidal activities. In particular, (Z)-ethoxyethyl 2-cyano-3-isopropyl-3-(2-chlorothiazol-5-yl)methylaminoacrylate showed excellent herbicidal activities even at a dose of 75 g/ha. A suitable group at the 3-position of acrylate was essential for high herbicidal activity. 2-Cyanoacrylates containing a 2-chloro-5-thiazolyl group are a novel class of herbicides and display herbicidal activities comparable to existing analogues bearing chloropyridyl or chlorophenyl.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyanoacrylates / chemical synthesis*
  • Cyanoacrylates / pharmacology
  • Electron Transport / drug effects
  • Herbicides / chemical synthesis*
  • Photosystem II Protein Complex / drug effects
  • Structure-Activity Relationship
  • Thiazoles / chemical synthesis
  • Thiazoles / pharmacology

Substances

  • Cyanoacrylates
  • Herbicides
  • Photosystem II Protein Complex
  • Thiazoles