Synthesis of some novel phosphorylated and thiophosphorylated benzimidazoles and benzothiazoles and their evaluation for larvicidal potential to Aedes albopictus and Culex quinquefasciatus

Bioorg Med Chem Lett. 2014 Jul 1;24(13):2934-9. doi: 10.1016/j.bmcl.2014.04.082. Epub 2014 Apr 30.

Abstract

Series of benzimidazole and benzothiazole linked phosphoramidates and phosphoramidothioates (5a-j) and benzimidazole linked phenylphosphoramidates and phenylphosphoramidothioates (10a-e) were synthesized. The title compounds were preliminary screened for mosquito larvicidal properties against Aedes albopictus and Culex quinquefasciatus at different concentration from 40 to 5 mg/L. Among the screened compounds three compounds revealed potential larvicidal effects with 100% mortality in the order of 10e>5j>5e. Compound 10e was found to be the most toxic compound to Ae. albopictus and Cx. quinquefasciatus. The LC50 of 10e against Ae. albopictus was found to be 6.42 and 5.25 mg/L at 24 and 48 h, respectively, whereas it was 7.01 and 3.88 mg/L, respectively in Cx. quinquefasciatus. Temephos was used as positive control.

Keywords: Aedes albopictus; Benzimidazole/benzothiazole; Culex quinquefasciatus; Larvicidal activity; Phosphoramidate/phosphoramidothioate.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aedes / drug effects*
  • Animals
  • Benzimidazoles / chemical synthesis
  • Benzimidazoles / chemistry
  • Benzimidazoles / pharmacology*
  • Benzothiazoles / chemical synthesis
  • Benzothiazoles / chemistry
  • Benzothiazoles / pharmacology*
  • Culex / drug effects*
  • Dose-Response Relationship, Drug
  • Insecticides / chemical synthesis
  • Insecticides / chemistry
  • Insecticides / pharmacology*
  • Molecular Structure
  • Phosphorylation
  • Structure-Activity Relationship

Substances

  • Benzimidazoles
  • Benzothiazoles
  • Insecticides