Synthesis and biological activity of fluorescent neonicotinoid insecticide thiamethoxam

Bioorg Med Chem Lett. 2014 Aug 1;24(15):3552-5. doi: 10.1016/j.bmcl.2014.05.052. Epub 2014 May 27.

Abstract

Here, we describe the synthesis of two new fluorescent derivatives of thiamethoxam and compared their toxicity on aphid Acyrthosiphon pisum and their mode of action on insect nicotinic acetylcholine receptors expressed on the sixth abdominal ganglion. The compound 3 with two 2-chlorothiazole moieties was found to be more toxic using toxicological bioassays 24 h and 48 h after exposure while compound 4 appeared more active using cockroach ganglionic depolarization. Interestingly, thiamethoxam appeared more effective than component 3 and 4, respectively. Our results demonstrated that component 3 and 4 act as agonists of insect nicotinic acetylcholine receptors.

Keywords: Insect; Insecticide; Neonicotinoid; Nicotinic receptor; Thiamethoxam.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Aphids / drug effects*
  • Dose-Response Relationship, Drug
  • Fluorescent Dyes / chemical synthesis
  • Fluorescent Dyes / chemistry
  • Fluorescent Dyes / pharmacology*
  • Insecticides / chemical synthesis
  • Insecticides / chemistry
  • Insecticides / pharmacology*
  • Molecular Conformation
  • Neonicotinoids
  • Nitro Compounds / chemical synthesis
  • Nitro Compounds / chemistry
  • Nitro Compounds / pharmacology*
  • Oxazines / chemical synthesis
  • Oxazines / chemistry
  • Oxazines / pharmacology*
  • Receptors, Nicotinic / metabolism*
  • Structure-Activity Relationship
  • Thiamethoxam
  • Thiazoles / chemical synthesis
  • Thiazoles / chemistry
  • Thiazoles / pharmacology*

Substances

  • Fluorescent Dyes
  • Insecticides
  • Neonicotinoids
  • Nitro Compounds
  • Oxazines
  • Receptors, Nicotinic
  • Thiazoles
  • Thiamethoxam