Synthesis and insecticidal activity study of novel anthranilic diamides analogs containing a diacylhydrazine bridge as effective Ca2+ modulators

Chem Biol Drug Des. 2018 Nov;92(5):1914-1919. doi: 10.1111/cbdd.13349. Epub 2018 Jul 15.

Abstract

Anthranilic diamides is a class of insecticides target at ryanodine receptors (RyRs). To discover potent insecticides targeting at RyRs, a series of novel anthranilic diamides with a diacylhydrazine bridge were designed and synthesized. Their insecticidal activities were evaluated and a preliminary structure-activity relationship (SAR) was summarized. In particular, compound 5g exhibited good lethality against oriental armyworm (Mythimna separata) at a concentration of 5 mg/L. The calcium imaging experimental results indicated that the compound 5g can serve as effective insect Ca2+ level modulators by disrupting the cellular calcium homeostasis in Mythimna separata (Walker) and Spodoptera exigua (Hübner), which probably activated the RyRs on the ER membrane.

Keywords: Ca2+ modulator; anthranilic diamides; diacylhydrazine; ryanodine receptors.

Publication types

  • Letter
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Calcium / metabolism*
  • Diamide / analogs & derivatives*
  • Diamide / chemical synthesis
  • Diamide / pharmacology
  • Drug Design
  • Hydrazines / chemistry*
  • Insecticides / chemical synthesis*
  • Insecticides / chemistry
  • Insecticides / pharmacology
  • Neurons / cytology
  • Neurons / drug effects
  • Neurons / metabolism
  • Spodoptera / drug effects
  • Structure-Activity Relationship
  • ortho-Aminobenzoates / chemistry*

Substances

  • Hydrazines
  • Insecticides
  • ortho-Aminobenzoates
  • anthranilic acid
  • Diamide
  • hydrazine
  • Calcium