Design, Synthesis and Antifungal Activity of Novel Thioureas Containing 1,3,4-Thiadiazole and Thioether Skeleton

doi:10.1007/s40242-016-6023-8

Chemical Research in Chinese Universities ›› 2016, Vol. 32 ›› Issue (4): 615-620.doi: 10.1007/s40242-016-6023-8

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Design, Synthesis and Antifungal Activity of Novel Thioureas Containing 1,3,4-Thiadiazole and Thioether Skeleton

WANG Caixia^1,2, SONG Hailong¹, LIU Weiqun^1,3, XU Cuilian²

1. College of Tobacco, Henan Agricultural University, Zhengzhou 450002, P. R. China;
2. College of Sciences, Henan Agricultural University, Zhengzhou 450002, P. R. China;
3. College of Life Sciences, Henan Agricultural University, Zhengzhou 450002, P. R. China

Received:2016-01-21 Revised:2016-05-24 Online:2016-08-01 Published:2016-06-06
Contact: LIU Weiqun, XU Cuilian E-mail:liuweiqun2004@126.com;xucuilian666@henau.edu.cn
Supported by:
Supported by the Key Science and Technique Foundation of Henan Province, China(No.112101110200) and the Basic Research Program of the Education Department of Henan Province, China(No.30600808).

Abstract

Abstract:

To find new lead compounds with high antifungal activity, a series of new thiourea derivatives containing 1,3,4-thiadiazole and thioether skeleton was designed via linking the active sub-structures. The target compounds were prepared via three steps from the commercially available thiosemicarbazide. Their structures were characterized by means of HRMS, ¹H NMR, ¹³C NMR and IR spectroscopy. The preliminary results indicate that the title compounds show various antifungal activity against the tested fungi. Compounds 4c, 4g, 4h, 4k, 4n, 4o, 4p, 4q and 4r display excellent antifungal activities against one or more tested fungi with inhibitory efficiencies of 90%-100% at 200 μg/mL. Especially, compound 4o shows the best inhibitory effect against Curvularia lunata, Cotton Fusarium Wilt, P. P. var nicotianae and Fusarium spp. with the EC₅₀ values of 28.12, 30.41, 15.2 and 6.22 μg/mL, respectively, which are even superior to those of triadimefon(98.73, 96.58, 105.37 and 102.18 μg/mL). The preliminary structure-activity relationship indicates that allyl and aromatic groups are favorable to their antifungal activities.

Key words: Thiourea, 2-Amino-5-alkylthio-1,3,4-thiadiazole, Antifungal activity

WANG Caixia, SONG Hailong, LIU Weiqun, XU Cuilian. Design, Synthesis and Antifungal Activity of Novel Thioureas Containing 1,3,4-Thiadiazole and Thioether Skeleton[J]. Chemical Research in Chinese Universities, 2016, 32(4): 615-620.

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Design, Synthesis and Antifungal Activity of Novel Thioureas Containing 1,3,4-Thiadiazole and Thioether Skeleton

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