Design, Synthesis, and Synergistic Activities of Eight-Membered Carbon Bridged Neonicotinoid Derivatives

Chem Biodivers. 2024 Feb;21(2):e202301412. doi: 10.1002/cbdv.202301412. Epub 2024 Jan 18.

Abstract

Insecticide synergists are an effective approach to increase the control efficacy and reduce active ingredient usage. In order to explore neonicotinoid-specific synergists with novel scaffolds and higher potency, a series of eight-membered carbon bridged neonicotinoid derivatives were designed and synthesized in accordance with our previous research. The synergistic effects of the target compounds on neonicotinoids in Aphis craccivora were evaluated, and the structure-activity relationships were summarized. The results indicated that most of the target compounds exhibited significant synergistic effects on imidacloprid in A. craccivora at low concentrations. In particular, compound 1 at a concentration of 1 mg/L reduced the LC50 value of imidacloprid from 0.856 mg/L to 0.170 mg/L. Meanwhile, compound 1 also increased the insecticidal activity of most neonicotinoid insecticides belonging to the Insecticide Resistance Action Committee (IRAC) 4 A subgroup against A. craccivora. The present study might be meaningful for directing the design of neonicotinoid-specific synergists.

Keywords: eight-membered carbon bridged; imidacloprid; neonicotinoid; synergistic effect.

MeSH terms

  • Animals
  • Aphids*
  • Insecticides* / pharmacology
  • Neonicotinoids / pharmacology
  • Nitro Compounds / pharmacology

Substances

  • imidacloprid
  • Neonicotinoids
  • Insecticides
  • Nitro Compounds