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Fifteen novel carbazole derivatives of 2-(9 H -carbazol-9-yl)- N -(5-phenyl-1,3,4-thiadiazol-2-yl)acetamide were designed, synthesized and evaluated for their antifungal activities against  Pellicularia sasakii  ( P. sasakii ),  Fusarium oxysporum  ( F. oxysporum ),  Gibberella zeae  ( G. zeae ),  Phytophthora infestans  ( P. infestans ),  Cytospora mandshurica  ( C. mandshurica ) and  Capsicum wilt  ( C. wilt ). The results of antifungal activity tests indicated that the inhibitory rates of compounds 2-(2-chloro-9 H -carbazol-9-yl)- N -(5-(4-fluorophenyl)-1,3,4-thiadiazol-2-yl)acetamide ( 3h ) and 2-(2-chloro-9 H -carbazol-9-yl)- N -(5-(thiophen-2-yl)-1,3,4-thiadiazol-2-yl)acetamide ( 3o ) against  P. sasakii  were 72.89% and 74.29%, respectively, which displayed better bioactivity compared with commercial fungicides hymexazol (53.09%) and carbendazim (69.65%). Meanwhile, compounds 2-(9 H -carbazol-9-yl)- N -(5-(thiophen-2-yl)-1,3,4-thiadiazol-2-yl)acetamide ( 3f ) and 2-(3-iodo-9 H -carbazol-9-yl)- N -(5-(p-tolyl)-1,3,4-thiadiazol-2-yl)acetamide ( 3 l ) exhibited the inhibition rates of 72.40% and 67.65% against  C. wilt , respectively, which were better than the commercial fungicides hymexazol (50.21%) and carbendazim (65.33%).

Discovery of novel carbazole derivatives containing a 1,3,4-thiadiazole moiety as antifungal candidates