Mosquito larvicidal activity of pyrrolidine-2,4-dione derivatives: An investigation against Culex quinquefasciatus and molecular docking studies

Abstract

The pyrrolidine-2,4-dione derivatives were used to conduct a larvicidal test on Culex quinquefasciatus larvae of the second instar. Mannich base condensation method was used to synthesis the pyrrolidine-2,4-dione derivatives by grindstone method. The reaction conditions were mild, resulting in high yields. An analysis of the synthesized compounds was carried out using FTIR, ¹H NMR, ¹³C NMR, mass spectrometry, and elemental analysis. Synthesized compounds (1a-h) were evaluated for larvicidal activities. Compound 1e (LD₅₀: 26.06 µg/mL), and 1f (LD₅₀: 26.89 µg/mL), and were notably more active against Culex quinquefasciatus than permethrin (LD₅₀: 26.14 µg/mL). The docking studies also demonstrated that 1e, and 1f are potent larvicides with higher binding energy (-12.6 kcal/mol) than the control in the mosquito odorant binding protein (PDB ID: 3OGN). The larvicidal properties of lead molecules have made them important for use as insecticides.

Keywords: 4-dione derivative; Culex quinquefasciatus; Grindstone chemistry; Larvicidal activity; Mannich base; Molecular docking; Pyrrolidine-2.

Fig. 1

Some bioactive naturally existing pyrrolidine-2,4-dione.

Scheme 1

Synthetic route of compound pyrrolidine-2,4-dione derivatives.

Fig. 2

2D representation molecule docked with receptor of compound 1a-1h.

Fig. 3

Highly active compound 1e shows docking with mosquito odorant binding protein (3OGN).