Synthesis, insecticidal activity, and ensembled docking of nitroguanidines bearing S- and R-proline.
Pest Manag Sci
; 79(5): 1912-1921, 2023 May.
Article
in En
| MEDLINE
| ID: mdl-36656155
ABSTRACT
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.Key words
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Receptors, Nicotinic
/
Insecticides
Limits:
Animals
Language:
En
Journal:
Pest Manag Sci
Journal subject:
TOXICOLOGIA
Year:
2023
Type:
Article
Affiliation country:
Mexico