Synthesis of new fluorinated Tebufenpyrad analogs with acaricidal activity through regioselective pyrazole formation

J Org Chem. 2008 Nov 7;73(21):8545-52. doi: 10.1021/jo801729p. Epub 2008 Oct 15.

Abstract

In previous studies, our group has shown that the use of fluorinated alcohols such as trifluoroethanol (TFE) and hexafluoroisopropanol (HFIP) as solvents dramatically increases the regioselectivity in the pyrazole formation from 1,3-diketone with methylhydrazine. We have now applied this synthetic method to the preparation of new fluorinated pyrazoles, which have then been used as synthetic intermediates in the preparation of fluorinated analogs of Tebufenpyrad, a commercial acaricide. These compounds display a strong acaricidal activity that is either comparable to or better than that of the commercial compound.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acaridae / drug effects*
  • Animals
  • Halogenation
  • Pesticides / chemical synthesis*
  • Pesticides / pharmacology
  • Pyrazoles / chemical synthesis
  • Pyrazoles / chemistry*

Substances

  • Pesticides
  • Pyrazoles
  • 4-chloro-N-((4-(1,1-dimethylethyl)phenyl)methyl)-3-ethyl-1-methyl-1H-pyrazole-5-carboxamide