l‑Proline as a Valuable Scaffold for the Synthesis of Novel Enantiopure Neonicotinoids Analogs

• Published in: Journal of agricultural and food chemistry Vol. 69; no. 5; pp. 1455 - 1465
• Main Authors: Bonilla-Landa, Israel, Cuapio-Muñoz, Ulises, Luna-Hernández, Axel, Reyes-Luna, Alfonso, Rodríguez-Hernández, Alfredo, Ibarra-Juarez, Arturo, Suarez-Mendez, Gabriel, Barrera-Méndez, Felipe, Caram-Salas, Nadia, Enríquez-Medrano, J. Francisco, Díaz de León, Ramón E, Olivares-Romero, José Luis
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 10-02-2021
• Subjects: Agricultural and Environmental Chemistry; Animals; Coleoptera - drug effects; Coleoptera - growth & development; Insecticides - chemical synthesis; Insecticides - chemistry; Insecticides - pharmacology; Molecular Docking Simulation; Molecular Structure; Neonicotinoids - chemical synthesis; Neonicotinoids - chemistry; Neonicotinoids - pharmacology; Proline - chemistry; enantiopure compound; docking; nitroguanidines; chiral; insecticidal activity; neonicotinoids
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/acs.jafc.0c05997

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.