cis-Nitenpyram Analogues Bearing Acyloxy Segments Anchored on the Tetrahydropyrimidine Ring： Synthesis, Insecticidal Activities and Molecular Docking Studies

A series of novel cis-nitenpyram analogues bearing acyloxy segments anchored on the tetrahydropyrimi-dine ring was designed and synthesized. Preliminary bioassays indicate that all the nitenpyram analogues 3a--3n exhibit good insecticidal activities against Nilaparvata lugens and Aphis medicaginis a...

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Bibliographic Details
Published in:Chemical research in Chinese universities 2013-06, Vol.29 (3), p.477-482
Main Authors: Sun, Chuan-wen, Wu, Ying, Chen, Yan-xia, Nan, Shi-bin, Zhang, Wang-geng
Format: Article
Language:English
Subjects:
Analytical Chemistry
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Inorganic Chemistry
Organic Chemistry
Physical Chemistry
分子对接
合成
杀虫活性
烯啶虫胺
类似物
轴承
锚段
顺式
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Summary:A series of novel cis-nitenpyram analogues bearing acyloxy segments anchored on the tetrahydropyrimi-dine ring was designed and synthesized. Preliminary bioassays indicate that all the nitenpyram analogues 3a--3n exhibit good insecticidal activities against Nilaparvata lugens and Aphis medicaginis at 100 mg/L, while analogue 3k affords the best activity in vitro and the lethal concentration 50（LC50） values（0.187, 0.214 mg/L） are close to that of nitenpyram. The structure activity relationships（SARs） suggest that their insecticidal potency is influenced by the species of acyloxy segments. The docking results reveal that analogue 3k forms stronger hydrogen-bonding with the nAChR, which explain the structure activity relationships（SARs） observed in vitro and imply that the strategies of our designed nitenpyram analogues are feasible.
ISSN:1005-9040
2210-3171
DOI:10.1007/s40242-013-2347-9