Synthesis and herbicidal activities of novel 3-N-substituted amino-6-methyl-4-(3-trifluoromethylphenyl)pyridazine derivatives

J Agric Food Chem. 2008 Aug 13;56(15):6567-72. doi: 10.1021/jf800900h. Epub 2008 Jul 8.

Abstract

4-(3-Trifluoromethylphenyl)pyridazine is a new series of compounds with bleaching and herbicidal activities. Starting from ethyl 2-(3-trifluoromethylphenyl)acetate, an important intermediate 7 was synthesized in five steps with a moderate total yield of 51.5% in a safe and practical way. Twenty-six novel 3-N-substituted amino-6-methyl-4-(3-trifluoromethylphenyl)pyridazine derivatives were synthesized and evaluated through a Spirodela polyrrhiza test and greenhouse test. Some compounds can completely inhibit Chl at 1 microg/mL and exhibit equal or higher herbicidal activities with the commercial bleaching herbicide diflufenican against dicotyledonous plants at a rate of 75 g/ha.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Araceae / drug effects
  • Herbicides / chemical synthesis*
  • Herbicides / pharmacology*
  • Pyridazines / chemical synthesis*
  • Pyridazines / chemistry
  • Pyridazines / pharmacology*

Substances

  • Herbicides
  • Pyridazines