Synthesis, insecticidal activity, and ensembled docking of nitroguanidines bearing S‐ and R‐proline

BACKGROUND The amino acids R‐ and S‐proline were used to synthesize novel neonicotinoid derivatives that, after being characterized by 1H, DEPTQ 135, and HRMS–QTOF, were evaluated for use as insecticides against Galleria mellonella (caterpillar), Sitophilus zeamais, Xylosandrus morigerus, Xyleborus...

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Published in:Pest management science 2023-05, Vol.79 (5), p.1912-1921
Main Authors: 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
Format: Article
Language:English
Subjects:
Absolute configuration
Acetylcholine receptors (nicotinic)
Amino acids
Animals
Biological activity
Biological effects
chirality
docking
Enantiomers
Insecta - metabolism
insecticidal activity
Insecticides
Insecticides - chemistry
Insects
neonicotinoid
Neonicotinoids - chemistry
Plant protection
Proline
Receptors
Receptors, Nicotinic - metabolism
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Summary:BACKGROUND The amino acids R‐ and S‐proline were used to synthesize novel neonicotinoid derivatives that, after being characterized by 1H, 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. The R6 nitroguanidine derivative exhibits outstanding insecticidal activity against five pest insects, with up to 100% mortality. Docking revealed that π–π interactions are important to get a good docking score. The results suggest a correlation between absolute configuration and biological activity.
ISSN:1526-498X
1526-4998
DOI:10.1002/ps.7368