Synthesis and Insecticidal Activity of Nitroguanidines Featuring $R$- and $S$-Proline

Fresh neonicotinoid derivatives were crafted by utilizing R- and S-proline amino acids as foundational materials. These compounds were subjected to IH characterization and subsequently evaluated for their efficacy as insecticides against various pests: Xyleborus ferrugineus, Galleria m ellon ella (caterpillar), Xyleborus affinis, Sitophilus zeamais, and Xylosandrus morigerus. The
$R$
enantiomer outperformed dinotefuran at equivalent concentrations in terms of insecticidal activity, causing fatality rates of up to 100% within 12 hours. It displayed outstanding insecticidal potential, making it a possible contender for crop protection measures in the future. Furthermore, an intermolecular interactions study revealed that it has a higher affinity for nicotinic acetylcholine receptors than the S enantiomer, which is due to stable - contacts. This work introduces neonicotinoid derivatives with potent insecticidal properties, emphasizing the exceptional effectiveness of the
$R$
enantiomer, and compound R-(7) stands out as a promising lead insecticide, offering insights for advancing sustainable pest management and crop protection practices.