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).

Incorporating the photoisomerizable azobenzene into imidacloprid produced a photoswitchable insecticidal molecule as the first neonicotinoid example of remote control insecticide performance with spatiotemporal resolution. The designed photoswitchable insecticides showed distinguishable activity against Musca both in vivo and in vitro upon irradiation. Molecular docking study further suggested the binding difference of the two photoisomers. The generation of these photomediated insecticides provides novel insight into the insecticidal activity facilitating further investigation on the functions of insect nicotinic acetylcholine receptors and opens a novel way to control and study insect behavior on insecticide poisoning using light.