Imidacloprid derivatives with the nitromethylene moiety and a substituent at the 5 position of the imidazolidine ring were synthesized to evaluate their insecticidal activity and affinity to the nicotinic acetylcholine receptor. Comparison of the receptor affinity of alkylated derivatives with that of the compounds having either an ether or thioether group, demonstrated that the replacement of the carbon atom of the alkyl group to the oxygen atom lowered the affinity, whereas the replacement to the sulfur atom did not change it. The receptor affinity of a compound having the benzyl group was lower than that of the unsubstituted one. A positive correlation between the receptor affinity and the insecticidal activity was observed when log P and the possession of the heteroatoms in the substituent were considered, suggesting that not only the receptor affinity but also other factors such as hydrophobicity and metabolism are important for insecticidal activity.

Effect of the substituents at the 5-position of the imidazolidine ring of imidacloprid derivatives on their biological activities

248th National Meeting (2014)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.