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 exhi...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.展开更多
To make further studies on the difference of cis-nitenpyram analogues, a series of cis-nitenpyram com- pounds containing a flexible amido segment anchored on tetrahydropyrimidine ring was designed and synthesized. Pre...To make further studies on the difference of cis-nitenpyram analogues, a series of cis-nitenpyram com- pounds containing a flexible amido segment anchored on tetrahydropyrimidine ring was designed and synthesized. Preliminary bioassays indicate that all the analogues exhibit a mortality of 100% at 100 rag/L, and the analogue 4d shows the best activity against Nilaparvata lugens and Myzus persicae, with a mortality of 100% at 4 mg/L （LCs0=0.172 rag/L）. The structure activity relationship studies show that insecticidal activities of the analogues are affected by the kinds and size of substituent R. In addition, the molecular docking simulations reveal that compouds 4 with a flexible amido segment on tetrahydropyrimidine ring show their different binding affinities for the nicotinic acetyleholine receptor（nAChR） of insect and compoud 4d shows stronger hydrogen-bonding with nAChR, which may provide the structure-activity relationship observed in vitro.展开更多
基金Supported by the National Natural Science Foundation of China（Nos.21042010, 21102092 and 30870560）, the Key Scientific ＂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）.
文摘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.
文摘To make further studies on the difference of cis-nitenpyram analogues, a series of cis-nitenpyram com- pounds containing a flexible amido segment anchored on tetrahydropyrimidine ring was designed and synthesized. Preliminary bioassays indicate that all the analogues exhibit a mortality of 100% at 100 rag/L, and the analogue 4d shows the best activity against Nilaparvata lugens and Myzus persicae, with a mortality of 100% at 4 mg/L （LCs0=0.172 rag/L）. The structure activity relationship studies show that insecticidal activities of the analogues are affected by the kinds and size of substituent R. In addition, the molecular docking simulations reveal that compouds 4 with a flexible amido segment on tetrahydropyrimidine ring show their different binding affinities for the nicotinic acetyleholine receptor（nAChR） of insect and compoud 4d shows stronger hydrogen-bonding with nAChR, which may provide the structure-activity relationship observed in vitro.
