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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.

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