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Synthesis, Insecticidal Activity, Crystal Structure, and Molecular Docking Studies of Nitenpyram Analogues with an ω‑Hydroxyalkyl Ester Arm Anchored on the Tetrahydropyrimidine Ring

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posted on 26.09.2012, 00:00 by Chuan-Wen Sun, Ting Fang, Jing Wang, Zhi-bing Hao, Shi-bing Nan
On the basis of the research of the proposed modes of action between neonicotinoids and insect nicotinic acetylcholine receptor (nAChR), a new series of nitenpyram analogues with an ω-hydroxyalkyl ester arm anchored on the tetrahydropyrimidine ring was designed and synthesized to further enhance the strength of the hydrogen-bonding action they display in binding with the nAChR. The structures of the target compounds were characterized by 1H NMR, IR, and elemental analysis, and the cis configuration was confirmed by X-ray diffraction. Preliminary bioassays indicated that all of the nitenpyram analogues exhibited good insecticidal activity against Nilaparvata lugens and Myzus persicae at 100 mg/L, whereas analogues 4d and 6a afforded the best in vitro activity that had ≥95% mortality at 4 mg/L; the LC50 values of the analogues 4d and 6a were 0.170 and 0.154 mg/L, respectively. Structure–activity relationship (SAR) studies suggested that their insecticidal potency was also dual-controlled by the flexibility and size of the molecule. In addition, molecular docking simulations revealed that analogues 4d and 6a displayed stronger hydrogen-bonding action in binding with the nAChR, which explained the SARs observed in vitro and implied that the designed nitenpyram analogues are both practical and feasible.