Pyrrole- and Dihydropyrrole-Fused Neonicotinoids: Design, Synthesis, and Insecticidal Evaluation

Versatile pyrrole- and dihydropyrrole-fused neonicotinoids
were
obtained from cyclic and non-cyclic nitroeneamines. Anhydrous aluminum
chloride (AlCl3) exhibited high catalytic selectivity for
the synthesis of the titled etherified compounds at room temperature
and the eliminated products under reflux conditions. The target molecules
have been identified on the basis of satisfactory analytical and spectral
[1H and 13C nuclear magnetic resonance (NMR),
high-resolution mass spectrometry (HRMS), and X-ray] data. All synthesized
compounds have been screened for insecticidal activity. The preliminary
insecticidal activity results showed that some of the aimed compounds
displayed excellent insecticidal activity against cowpea aphids (Aphis craccivora).