Iodine-mediated oxidative cyclization for one pot synthesis of new 8-hydroxyquinaldine derivatives containing a N-phenylpyrazole moiety as pesticidal agents

Bioorg Med Chem Lett. 2018 Nov 1;28(20):3376-3380. doi: 10.1016/j.bmcl.2018.08.041. Epub 2018 Sep 1.

Abstract

In continuation of our research aimed at discovery and development of new pesticidal agents, a series of new 8-hydroxyquinaldine derivatives containing a N-phenylpyrazole moiety were prepared and their structures were characterized by 1H NMR, IR, ESI-MS and mp. Meanwhile, an efficient way of using iodine-mediated oxidative cyclization for one pot synthesis of these 8-hydroxyquinaldine derivatives containing a N-phenylpyrazole moiety was developed. The bioassay showed that compounds 8g and 9f exhibited potent pesticidal activities against both Mythimna separata Walker and Plutella xylostella Linnaeus. The structure-activity relationships were also discussed.

Keywords: 8-Hydroxyquinaldine; N–Phenylpyrazole; Pesticidal activities; Structural modification; Structure–activity relationship.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cyclization
  • Insecticides / chemical synthesis
  • Insecticides / chemistry
  • Insecticides / toxicity*
  • Iodine / chemistry*
  • Molecular Structure
  • Moths / drug effects
  • Oxidation-Reduction
  • Pyrazoles / chemical synthesis
  • Pyrazoles / chemistry
  • Pyrazoles / toxicity*
  • Quinaldines / chemical synthesis
  • Quinaldines / chemistry
  • Quinaldines / toxicity*
  • Structure-Activity Relationship

Substances

  • Insecticides
  • Pyrazoles
  • Quinaldines
  • Iodine