Synthesis, Crystal Structure and Biological Activities of Phenyl(6-phenyl-3-p-tolyl-6,7-dihydro-5<em>H</em>-[1,2,4]triazolo-[3,4-b][1,3,4]thiadiazin-7-yl)methanone

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摘要 The title compound phenyl(6-phenyl-3-p-tolyl-6,7-dihydro-5H-[1,2,4]triazolo[3,4-b][1,3,4]thia- diazin-7-yl)methanone (PTM), designed using 4-amino-3-p-tolyl-1H-1,2,4-triazole-5(4H)-thione as the starting material, was successfully synthesized via a two-step synthesis route and finally characterized by NMR, FT-IR, single-crystal X-ray diffraction and mass spectrometry techniques. The crystal structure of trans-PTM was obtained from X-ray diffraction: C24H20N4OS, Mr = 412.52, monoclinic system, space group P21/c, a = 16.650(3), b = 13.876(3), c = 8.812(2) Å, β = 100.340(3)°, V = 2002.8(7) Å3, F(000) = 865, Z = 4, Dc = 1.3680 g/cm3, λ = 0.71073 Å, μ = 0.186 mm 1 and the final R = 0.0786 for 3514 unique reflections with 2044 observed ones (I > 2σ(I)). The biological activities of antimicrobial and regulation of plant growth of PTM were investigated. The results indicated that PTM showed weak antimicrobial activity on Bacillus pumilus, while promoted the growth of radish and inhibited that of wheat in a dose-dependent manner. Therefore, PTM may be developed as a potential drug to promote the growth of dicotyledonous plants or as an herbicide to inhibit that of monocotyledonous plants in the future.

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	丁其春
	邹毅辉
	李秋玲
	黄建军
	张力学
	尹慧勇

关键词 ： synthesis, 1,2,4-triazole, triazolothiadiazine, crystal structure, FT-IR, NMR, biological activity

Abstract：The title compound phenyl(6-phenyl-3-p-tolyl-6,7-dihydro-5H-[1,2,4]triazolo[3,4-b][1,3,4]thia- diazin-7-yl)methanone (PTM), designed using 4-amino-3-p-tolyl-1H-1,2,4-triazole-5(4H)-thione as the starting material, was successfully synthesized via a two-step synthesis route and finally characterized by NMR, FT-IR, single-crystal X-ray diffraction and mass spectrometry techniques. The crystal structure of trans-PTM was obtained from X-ray diffraction: C24H20N4OS, Mr = 412.52, monoclinic system, space group P21/c, a = 16.650(3), b = 13.876(3), c = 8.812(2) Å, β = 100.340(3)°, V = 2002.8(7) Å3, F(000) = 865, Z = 4, Dc = 1.3680 g/cm3, λ = 0.71073 Å, μ = 0.186 mm 1 and the final R = 0.0786 for 3514 unique reflections with 2044 observed ones (I > 2σ(I)). The biological activities of antimicrobial and regulation of plant growth of PTM were investigated. The results indicated that PTM showed weak antimicrobial activity on Bacillus pumilus, while promoted the growth of radish and inhibited that of wheat in a dose-dependent manner. Therefore, PTM may be developed as a potential drug to promote the growth of dicotyledonous plants or as an herbicide to inhibit that of monocotyledonous plants in the future.

Key words： synthesis 1,2,4-triazole triazolothiadiazine crystal structure FT-IR NMR biological activity

收稿日期: 2019-11-20 出版日期: 2020-08-12

基金资助:This work was supported by the grants from Zhangzhou Natural Science Foundation of China (No. ZZ2018J39);The work reported in this manuscript has been granted a Chinese Patent (No. ZL201710632570.6)

通讯作者: 177426824@qq.com E-mail: 177426824@qq.com

引用本文:

丁其春;邹毅辉;李秋玲;黄建军;张力学;尹慧勇. Synthesis, Crystal Structure and Biological Activities of Phenyl(6-phenyl-3-p-tolyl-6,7-dihydro-5H-[1,2,4]triazolo-[3,4-b][1,3,4]thiadiazin-7-yl)methanone[J]. 结构化学, 2020, 39(8): 1531-1538.
DING Qi-Chun;ZOU Yi-Hui;LI Qiu-Ling;HUANG Jian-Jun;ZHANG Li-Xue;YIN Hui-Yong. Synthesis, Crystal Structure and Biological Activities of Phenyl(6-phenyl-3-p-tolyl-6,7-dihydro-5H-[1,2,4]triazolo-[3,4-b][1,3,4]thiadiazin-7-yl)methanone. CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2020, 39(8): 1531-1538.

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http://manu30.magtech.com.cn/jghx/CN/ 或 http://manu30.magtech.com.cn/jghx/CN/Y2020/V39/I8/1531

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