Synthesis and fungicidal activities of novel bis(trifluoromethyl)phenyl-based strobilurins

J Agric Food Chem. 2008 Aug 13;56(15):6562-6. doi: 10.1021/jf800651z. Epub 2008 Jul 4.

Abstract

Strobilurins have become one of the most important classes of agricultural fungicides. To search for novel strobilurin compounds with unique biological activities, novel bis(trifluoromethyl)phenyl-based strobilurin analogues were synthesized by the reaction of 1-bis(trifluoromethyl)phenyl based methanone oxime with corresponding strobilurin pharmacophores in the presence of bases such as potassium hydroxide, potassium carbonate, or sodium hydride. ( E)-Methyl 2-(2-(((( Z)(1-(3,5-bis(trifluoromethyl) phenyl)-1-methoxymethylidene)amino)oxy)methyl)phenyl)-3-methoxyacrylate and ( Z)-methyl- N-( E)-2-(( E)-(5,6-dihydro-1,4,2-dioxazin-3-yl)(methoxyimino)methyl)benzyloxy-3,5-bis(trifluoromethyl)benzimidate were more effective against Erysiphe graminis and sphaerotheca fuligine than commercial strobilurin fungicides metominostrobin, azoxystrobin, and trifloxystrobin.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Ascomycota / drug effects
  • Fungicides, Industrial / chemical synthesis*
  • Fungicides, Industrial / pharmacology*
  • Methacrylates / chemical synthesis*
  • Methacrylates / pharmacology*
  • Structure-Activity Relationship

Substances

  • Fungicides, Industrial
  • Methacrylates