Rodríguez-Hernández Alfredo, Bonilla-Landa Israel, Vidal-Limon Abraham, Ibarra-Juárez Arturo, Barrera-Méndez Felipe, Medrano Francisco Javier Enríquez, Díaz de León Ramón E, Olivares-Romero José Luis
Instituto de Ecología, A.C, Red de Estudios Moleculares Avanzados, Clúster Científico y Tecnológico BioMimic, Veracruz, Mexico.
Cátedra CONACyT en el Instituto de Ecología, A. C, Veracruz, Mexico.
Pest Manag Sci. 2023 May;79(5):1912-1921. doi: 10.1002/ps.7368. Epub 2023 Feb 3.
The amino acids R- and S-proline were used to synthesize novel neonicotinoid derivatives that, after being characterized by H, DEPTQ 135, and HRMS-QTOF, were evaluated for use as insecticides against Galleria mellonella (caterpillar), Sitophilus zeamais, Xylosandrus morigerus, Xyleborus affinis, and Xyleborus ferrugineus.
Comparisons of biological activity and absolute configuration showed that the R enantiomer had excellent and outstanding insecticidal activity against the insects tested, with up to 100% mortality after 12 h compared with dinotefuran at the same concentration.
The results suggest that compound R6 is an excellent lead enantiopure insecticide for future development in the field of crop protection. Furthermore, intermolecular interactions between nicotinic acetylcholine receptors and the R enantiomer displays a lower score which mean a higher affinity to the nAChR receptor and the π-π interactions are more stable than the S derivative. © 2023 Society of Chemical Industry.
使用R-和S-脯氨酸合成了新型新烟碱类衍生物，经氢谱、DEPTQ 135和高分辨质谱-四极杆飞行时间质谱（HRMS-QTOF）表征后，评估其作为杀虫剂对大蜡螟（毛虫）、玉米象、暗梗长蠹、嗜虫长蠹和锈色长蠹的杀虫效果。
生物活性和绝对构型的比较表明，R对映体对受试昆虫具有优异且突出的杀虫活性，在相同浓度下，与呋虫胺相比，12小时后死亡率高达100%。
结果表明，化合物R6是未来作物保护领域开发的一种优秀的单一手性对映体杀虫剂。此外，烟碱型乙酰胆碱受体与R对映体之间的分子间相互作用得分较低，这意味着对nAChR受体具有更高的亲和力，且π-π相互作用比S衍生物更稳定。©2023化学工业协会。
