Citation: Zhang Yan, Zhan Yi-Zhou, Ma Yi, Hua Xue-Wen, Wei Wei, Zhang Xiao, Song Hai-Bin, Li Zheng-Ming, Wang Bao-Lei. Synthesis, crystal structure and 3D-QSAR studies of antifungal (bis-) 1, 2, 4-triazole Mannich bases containing furyl and substituted piperazine moieties[J]. Chinese Chemical Letters, ;2018, 29(3): 441-446. doi: 10.1016/j.cclet.2017.08.035 shu

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

State Key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering(Tianjin), College of Chemistry, Nankai University, Tianjin 300071, China

Corresponding author: Wang Bao-Lei, nkwbl@nankai.edu.cn
Received Date: 27 April 2017
Revised Date: 8 August 2017
Accepted Date: 15 August 2017
Available Online: 31 March 2017

Figures(6)

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.
- Triazole,
- Furan-2-yl,
- Mannich base,
- Antifungal activity,
- Herbicidal activity,
- 3D-QSAR
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