Design, Synthesis and Bioactivities of Novel Dichloro-Allyloxy-Phenol-Containing Pyrazole Oxime Derivatives

Molecules. 2015 Dec 8;20(12):21870-80. doi: 10.3390/molecules201219811.

Abstract

In this study, in order to find novel biologically active pyrazole oxime compounds, a number of dichloro-allyloxy-phenol-containing pyrazole oximes were designed and synthesized according to the method of active group combination. All of the target compounds were confirmed by ¹H-NMR, (13)C-NMR and elemental analysis. In addition, bioassays showed that all of the newly synthesized compounds had no acaricidal activity against Tetranychus cinnabarinus and low insecticidal activity against Aphis craccivora at tested concentrations. However, most of them displayed excellent insecticidal activity against Oriental armyworm at a concentration of 500 μg/mL, and some designed compounds still exhibited potent insecticidal activity against Oriental armyworm even at the dose of 20 μg/mL, especially compounds 7f, 7n and 7p had 100%, 90% and 90% inhibition rates, respectively, which were comparable to that of the control pyridalyl.

Keywords: biological activity; dichloro-allyoxy-phenol; pyrazole oxime; synthesis.

MeSH terms

  • Allyl Compounds / chemistry
  • Animals
  • Aphids / drug effects*
  • Drug Design*
  • Insecticides / chemistry*
  • Insecticides / pharmacology*
  • Molecular Structure
  • Moths / drug effects*
  • Oximes / chemistry*
  • Oximes / pharmacology
  • Phenols / chemistry
  • Pyrazoles / chemistry*
  • Pyrazoles / pharmacology*
  • Structure-Activity Relationship
  • Tetranychidae / drug effects*

Substances

  • 1-methyl-3-methyl-5-(2,4-difluorophenoxy)-1H-pyrazole-4-carbaldehyde-O-(4-(2,6-dichloro-4-(3,3-dichlollyoxy)-phenoxy)-n-butyl)-oxime
  • 1-methyl-3-methyl-5-(2-fluorophenoxy)-1H-pyrazole-4-carbaldehyde-O-(4-(2,6-dichloro-4-(3,3-dichloroallyoxy)-phenoxy)-n-butyl)-oxime
  • Allyl Compounds
  • Insecticides
  • Oximes
  • Phenols
  • Pyrazoles
  • pyrazole