Synthesis,crystal structure and 3D-QSAR studies of antifungal (bis-) 1,2,4-triazole Mannich bases containing furyl and substituted piperazine moieties  

作　　者：Yan Zhang Yi-Zhou Zhan Yi Ma Xue-Wen Hua Wei Wei Xiao Zhang Hai-Bin Song Zheng-Ming Li Bao-Lei Wang 

机构地区：[1]State Key Laboratory of Elemento-Organic Chemistry,Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), College of Chemistry,Nankai University

出　　处：《Chinese Chemical Letters》2018年第3期441-446,共6页中国化学快报（英文版）

基　　金：supported by the National Natural Science Foundation of China(No. 21372133);Tianjin Natural Science Foundation(No. 17JCYBJC19900)

摘　　要：A series of novel title compounds 6a-6r and 7a-7c have been synthesized by Mannich reaction of the new triazole Schiff base intermidiates, substituted piperazine and formaldehyde under mild conditions in excellent yields. The crystal structure of compound 6i was determined to show a chair conformation of the piperazine ring and an （E）-configuration of the C=N double bond. The bioassay results indicated that most of the newly synthesized compounds exhibited excellent in vitro inhibitory activities and broader spectrum against several plant fungi, and were more effective than the control Triadimefon. Several compounds also displayed favourable in vivo antifungal activities. The relationships between the compound structures and various biological activities were discussed. Furthermore, the CoMFA calculation based on the antifungal activity data of compounds 6 against R. cerealis was carried out to establish a 3D-QSAR model, which revealed that steric and electrostatic fields were two most important factors for contributing the bioactivity of the compounds. The present work will provide significant information for guiding optimization of such new structures to develop novel agrochemicals with higher antifungal activities.A series of novel title compounds 6a-6r and 7a-7c have been synthesized by Mannich reaction of the new triazole Schiff base intermidiates, substituted piperazine and formaldehyde under mild conditions in excellent yields. The crystal structure of compound 6i was determined to show a chair conformation of the piperazine ring and an （E）-configuration of the C=N double bond. The bioassay results indicated that most of the newly synthesized compounds exhibited excellent in vitro inhibitory activities and broader spectrum against several plant fungi, and were more effective than the control Triadimefon. Several compounds also displayed favourable in vivo antifungal activities. The relationships between the compound structures and various biological activities were discussed. Furthermore, the CoMFA calculation based on the antifungal activity data of compounds 6 against R. cerealis was carried out to establish a 3D-QSAR model, which revealed that steric and electrostatic fields were two most important factors for contributing the bioactivity of the compounds. The present work will provide significant information for guiding optimization of such new structures to develop novel agrochemicals with higher antifungal activities.

关 键 词：Triazole Furan-2-yl Mannich base Antifungal activity Herbicidal activity 3D-QSAR 

分 类 号：TQ450.1[化学工程—农药化工]