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Updated: Aug 13, 2025

Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
Published on: April 27, 2017
Synthesis, insecticidal activity, and ensembled docking of nitroguanidines bearing S- and R-proline
Alfredo Rodríguez-Hernández1, Israel Bonilla-Landa1, Abraham Vidal-Limon1
1Instituto de Ecología, A.C, Red de Estudios Moleculares Avanzados, Clúster Científico y Tecnológico BioMimic, Veracruz, Mexico.
Background:
The amino acids R- and S-proline were used to synthesize novel neonicotinoid derivatives that, after being characterized by 1 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.
Results:
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.
Conclusions:
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.
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