Design, synthesis and bioactivity evaluation of novel benzophenone hydrazone derivatives

Pest Manag Sci. 2014 Apr;70(4):667-73. doi: 10.1002/ps.3607. Epub 2013 Aug 13.

Abstract

Background: Benzophenone hydrazone derivatives are among the most important classes of synthetic insecticides. In an effort to discover new molecules with good insecticidal/acaricidal activities, a series of novel benzophenone hydrazone N-acylated thiourea and urea derivatives was synthesized and bioassayed.

Results: All of these compounds exhibited excellent bioactivities against T. cinnabarinus and B. brassicae, especially towards T. cinnabarinus with LC50 values ranging from 0.305 to 2.036 mmol L(-1). Moreover, the acaricidal activities against T. cinnabarinus of compounds 8a-i, 12b-f and 12h were 2.5-5.5-fold that of parent molecule 3 based on the LC50 value.

Conclusion: Based on the observed bioactivities, the structure-activity relationship of these analogs was also discussed. Structure-activity relationships provided information that could direct further investigation on structure modification. Our studies indicated that benzophenone hydrazone N-acylated thiourea and urea derivatives could be used as potential lead compounds for developing novel acaricides and insecticides.

Keywords: acaricide; benzophenone hydrozone; insecticide; structure-activity relationship; thiourea; urea.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acaricides / chemical synthesis*
  • Acaricides / toxicity
  • Animals
  • Aphids / drug effects
  • Benzophenones / chemistry
  • Benzophenones / toxicity
  • Biological Assay
  • Hydrazones / chemistry
  • Hydrazones / toxicity
  • Insecticides / chemical synthesis*
  • Insecticides / toxicity
  • Structure-Activity Relationship
  • Tetranychidae / drug effects

Substances

  • Acaricides
  • Benzophenones
  • Hydrazones
  • Insecticides