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

doi:10.1007/s40242-013-2347-9

Chemical Research in Chinese Universities ›› 2013, Vol. 29 ›› Issue (3): 477-482.doi: 10.1007/s40242-013-2347-9

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

SUN Chuan-wen^1,2, WU Ying¹, CHEN Yan-xia¹, NAN Shi-bin¹, ZHANG Wang-geng²

1. College of Life and Environment Sciences, Shanghai Normal University, Shanghai 200234, P. R. China;
2. Jiangsu Institute of Ecomones Co., Ltd., Jintan 213200, P. R. China

Received:2012-09-12 Revised:2012-10-09 Online:2013-06-01 Published:2013-05-15
Contact: Chuanwen SUN E-mail:willin112@163.com
Supported by:
Supported by the National Natural Science Foundation of China(Nos.21042010, 21102092 and 30870560), the Key Scienti- fic “Twelfth Five-Year” National Technology Support Program, China(No.2011BAE06B01-17), the Innovation Project of Shanghai Education Commission, China(No.12YZ078), the Program of the Food Safety and Nutrition Innovation Team of Shanghai Normal University, China(No.DXL123) and Shanghai Key Laboratory of Rare Earth Functional Materials, Shanghai Normal University, China(No.07dz22303)..

Abstract

Abstract:

A series of novel cis-nitenpyram analogues bearing acyloxy segments anchored on the tetrahydropyrimidine 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.

Key words: cis-Nitenpyram analogue, Acyloxy segment, Hydrogen-bonding action, Insecticidal activity, Molecular docking

SUN Chuan-wen, WU Ying, CHEN Yan-xia, NAN Shi-bin, ZHANG Wang-geng. cis-Nitenpyram Analogues Bearing Acyloxy Segments Anchored on the Tetrahydropyrimidine Ring: Synthesis,Insecticidal Activities and Molecular Docking Studies[J]. Chemical Research in Chinese Universities, 2013, 29(3): 477-482.

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

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