Synthesis, Acaricidal Activity, and Structure-Activity Relationships of Pyrazolyl Acrylonitrile Derivatives

J Agric Food Chem. 2016 Dec 28;64(51):9586-9591. doi: 10.1021/acs.jafc.6b04221. Epub 2016 Dec 15.

Abstract

A series of novel pyrazolyl acrylonitrile derivatives was designed, targeting Tetranychus cinnabarinus, and synthesized. Their structures were identified by combination of 1H NMR, 13C NMR, and MS spectra. The structures of compounds 18 and 19 were further confirmed by X-ray diffraction. Extensive greenhouse bioassays indicated that compound 19 exhibits excellent acaricidal activity against all developmental stages of T. cinnabarinus, which is better than the commercialized compounds cyenopyrafen and spirodiclofen. It was shown that the acute toxicity of compounds 19 to mammals is quite low. The structure-activity relationships are also discussed.

Keywords: acaricidal activity; acrylonitrile; pyrazolyl; spider mite; structure−activity relationship; synthesis.

MeSH terms

  • Acaricides / chemical synthesis
  • Acaricides / chemistry*
  • Acaricides / pharmacology*
  • Acrylonitrile / chemical synthesis
  • Acrylonitrile / chemistry*
  • Acrylonitrile / pharmacology*
  • Animals
  • Aphids / drug effects
  • Drug Design
  • Molecular Structure
  • Pyrazoles / chemical synthesis
  • Pyrazoles / chemistry*
  • Pyrazoles / pharmacology*
  • Structure-Activity Relationship
  • X-Ray Diffraction

Substances

  • Acaricides
  • Pyrazoles
  • Acrylonitrile