title: Synthesis and fungicidal activity of novel 2,5-disubstituted-1,3,4- thiadiazole derivatives containing 5-phenyl-2-furan.
abstract: 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.
authors.affiliation: Guangdong Province Key Laboratory of Microbial Signals and Disease Control, Department of Plant Pathology, South China Agricultural University, Guangzhou 510642, China.
authors.forename: Zi-Ning
authors.initials: ZN
authors.lastname: Cui
authors.affiliation: Guangdong Province Key Laboratory of Microbial Signals and Disease Control, Department of Plant Pathology, South China Agricultural University, Guangzhou 510642, China.
authors.forename: Ya-Sheng
authors.initials: YS
authors.lastname: Li
authors.affiliation: Guangdong Province Key Laboratory of Microbial Signals and Disease Control, Department of Plant Pathology, South China Agricultural University, Guangzhou 510642, China.
authors.forename: De-Kun
authors.initials: DK
authors.lastname: Hu
authors.affiliation: Guangdong Province Key Laboratory of Microbial Signals and Disease Control, Department of Plant Pathology, South China Agricultural University, Guangzhou 510642, China.
authors.forename: Hao
authors.initials: H
authors.lastname: Tian
authors.affiliation: Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China.
authors.forename: Jia-Zhen
authors.initials: JZ
authors.lastname: Jiang
authors.affiliation: Guangdong Province Key Laboratory of Microbial Signals and Disease Control, Department of Plant Pathology, South China Agricultural University, Guangzhou 510642, China.
authors.forename: Yuan
authors.initials: Y
authors.lastname: Wang
authors.affiliation: Institute of Plant Protection, Chinese Academy of Agricultural Sciences, Beijing 100193, China.
authors.forename: Xiao-Jing
authors.initials: XJ
authors.lastname: Yan
mesh_terms: D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D055750:Phytophthora infestans / Q000254:growth & development* / Q000648:ultrastructure; D013830:Thiadiazoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
chemical_list: D000935:Antifungal Agents; D013830:Thiadiazoles
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