Synthesis and fungicidal activity of novel 2,5-disubstituted-1,3,4- thiadiazole derivatives containing 5-phenyl-2-furan

A series of 2,5-disubstituted-1,3,4-thiadiazoles were synthesized using Lawesson’s reagent by an efficient approach under microwave irradiation in good yields. Their structures were characterized by MS, IR, 1 H NMR, 13 C NMR and elemental analysis. Their in vitro and in vivo fungicidal activities re...

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Bibliographic Details
Published in:Scientific reports 2016-01, Vol.6 (1), p.20204-20204, Article 20204
Main Authors: Cui, Zi-Ning, Li, Ya-Sheng, Hu, De-Kun, Tian, Hao, Jiang, Jia-Zhen, Wang, Yuan, Yan, Xiao-Jing
Format: Article
Language:English
Subjects:
140/131
631/92/613
639/638/403/908
Agricultural production
Antifungal Agents - chemical synthesis
Antifungal Agents - chemistry
Antifungal Agents - pharmacology
Bioassays
Biological activity
Biosynthesis
Cell walls
Fungi
Fungicidal activity
Fungicides
Humanities and Social Sciences
Hyphae
Irradiation
Morphology
multidisciplinary
NMR
Nuclear magnetic resonance
Pesticides
Phytophthora infestans - growth & development
Phytophthora infestans - ultrastructure
Reagents
Science
Senescence
Septation
Thiadiazoles - chemical synthesis
Thiadiazoles - chemistry
Thiadiazoles - pharmacology
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Summary:A series of 2,5-disubstituted-1,3,4-thiadiazoles were synthesized using Lawesson’s reagent by an efficient approach under microwave irradiation in good yields. Their structures were characterized by MS, IR, 1 H NMR, 13 C NMR and elemental analysis. Their in vitro and in vivo fungicidal activities revealed that the title compounds exhibited considerable activity against five selected fungi, especially to Phytophthora infestans . In order to illustrate the mechanism of title compounds against P. infestans , scanning electron micrographs (SEM) and transmission electron micrographs (TEM) were applied. The morphological and ultrastructural studies demonstrated that compound I18 led to swelling of hyphae, thickening and proliferating multilayer cell walls, excessive septation and accumulation of dense bodies. The bioassay results indicated compound I18 might act on cell wall biosynthesis and blocked the nutrition transportation and led to cells senescence and death. Meanwhile, compound I18 had broad fungicidal activity against other twenty different kinds of fungi. These results suggested that title compounds were eligible to be development candidates and compound I18 as a promising lead compound was worthy to be further discovery, especially against P. infestans.
ISSN:2045-2322
2045-2322
DOI:10.1038/srep20204