cis‐Nitenpyram Analogues Containing 1,4‐Dihydropyridine: Synthesis, Insecticidal Activities, and Molecular Docking Studies

Abstract

A novel series of cis-nitenpyram analogues (2a-2p) were designed and prepared by introducing the 1,4-dihydropyridine, with their cis-configuration confirmed by X-ray diffraction. Preliminary bioassays showed that most compounds exhibited good insecticidal activities at 20 mg/L against Aphis medicagini, and analogues 2a and 2d afforded the best activity, and both of them had 100% mortality at 4 mg/L. In addition, molecular docking studies were also performed to model the ligand-receptor complexes, and the results explained the structure-activity relationships observed in vitro, which may provide some useful information for future design of new insecticides.

1,4-Dihydropyridine: synthetic advances, medicinal and insecticidal properties

“…The insecticidal activity of cis -configured 1,4-DHPs against the most frequent pest, Aphis medicaginis , was enhanced ( Scheme 77 ). 107 In a related study, Rao and Parthiban (2014) successfully synthesized the cis -nitenpyram neonicotinoid insecticide analogue 77 by substituting 1-(6-chloropyridin-3-yl)- N -methylmethanamine 77b on 77a with good yield. The NO 2 group at the neonicotinoid's fifth position is crucial for enhancing the insecticidal efficacy, according to the literature.…”

(NH4)42[MoVI72MoV60O372(CH3COO)30(H2O)72] as a Heterogeneous Reusable Catalyst for Organic Reactions: Mini-Review

“…Compounds derived from xanthenes and 1,4dihydropyridines (1,4-DHPs) are of importance as they have various biological activities including, antibacterial [52], antiinflammatory [53], antimicrobial [54], antitubercular [55], neuroprotectant [56], and insecticidal activities [57]. Scheme 3.…”

Synthesis and Insecticidal Evaluation of Neonicotinoid Analogues with Bicyclic Ring System

“…至今, 昆虫的 nAChR 复合物晶体未有报道, 因此, 本工作采用结合吡虫啉的 Ac-AChBP 的复合物晶体结 构作为受体 [10,24,25] . 如图 3 所示, 图 3a 为目标化合物 6a 与 AChBP 的相互作用, 图 3b 为目标化合物 6a 与 AChBP 晶体结构中吡虫啉叠合图.…”