Xyleborus sp beetles are types of ambrosia beetles invasive to the United States and recently also to Mexico. The beetle can carry a fungus responsible for the Laurel Wilt, a vascular lethal disease that can host over 300 tree species, including redbay and avocado. This problem has a great economic and environmental impact. Indeed, synthetic chemists have recently attempted to develop new neonicotinoids. This is also due to severe drug resistance to “classic” insecticides. In this research, a series of neonicotinoids analogs were synthesized, characterized, and evaluated against Xyleborus sp. Most of the target compounds showed good to excellent insecticidal activity. Generally, the cyclic compounds also showed better activity in comparison with open-chain compounds. Compounds R-13, 23, S-29, and 43 showed a mortality percent of up to 73% after 12 h of exposure. These results highlight the enantioenriched compounds with absolute R configuration. The docking results correlated with experimental data which showed both cation-π interactions in relation to the aromatic ring and hydrogen bonds between the search cavity 3C79 and the novel molecules. The results suggest that these sorts of interactions are responsible for high insecticidal activity.
In this research, six neonicotinoid
analogs derived from l-proline were synthesized, characterized,
and evaluated as insecticides
against Xyleborus affinis. Most of the target compounds
showed good to excellent insecticidal activity. To the best of our
knowledge, this is the first report dealing with the use of enantiopure l-proline to get neonicotinoids. These results highlighted the
compound 9 as an excellent candidate used as the lead
chiral insecticide for future development. Additionally, molecular
docking with the receptor and compound 9 was carried
out to gain insight into its high activity when compared to dinotefuran.
Finally, the neurotoxic evaluation of compound 9 showed
lower toxicity than the classic neonicotinoid dinotefuran.
Asymmetric oxidation reaction is one of the significant pathways in stereoselective reactions, which is a prominent performer in academic and industrial research. However, ligands are vital for planning an ideal metal‐catalyzed asymmetric oxidation reaction as they interact with the metal to construct catalytically active metal complexes, which can catalyze numerous asymmetric reactions. Designing and synthesizing novel chiral ligands is essential for researchers in modern asymmetric synthesis. In this course, exploring the applicability and the survey of hydroxamic acid as a vital ligand has been presented, which is essential for various metal‐catalyzed transformations.
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