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Synthesis and Antifungal Activity of Novel Furan‐2,4‐dione Derivatives Containing Substituted Phenylhydrazine Moiety
Author(s) -
Hu Ying,
Zhang LiZhi,
Ren ZhengJiao,
Zhao Zheng,
Xu WenQin,
Yang ChunLong
Publication year - 2015
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.201400463
Subject(s) - botrytis cinerea , chemistry , phenylhydrazine , colletotrichum capsici , moiety , furan , proton nmr , antifungal , carbendazim , fungicide , stereochemistry , organic chemistry , botany , microbiology and biotechnology , biology
A series of novel 3‐(2‐(substituted phenyl)hydrazinylmethylidene)furan‐2,4(3 H ,5 H )‐diones were designed and synthesized with ethyl 4‐chloroacetoacetate as the starting material. Their structures were confirmed by FT‐IR, 1 H NMR, 13 C NMR, EI‐MS and elemental analysis. Bioassay data demonstrated that these compounds exhibited remarkable antifungal activity against Fusarium graminearum , Botrytis cinerea , Rhizoctonia cerealis and Colletotrichum capsici . Compound 3‐(2‐(4‐bromophenyl)hydrazinylmethylidene)furan‐2,4(3 H ,5 H )‐dione ( 5g ) had excellent bioactivity against Botrytis cinerea with an EC 50 value of 0.18 μg/mL ‐ markedly lower than the 0.24 μg/mL of the commercial fungicide procymidone. The result revealed that introducing the halogenated phenylhydrazine at the 3‐position of furan‐2,4(3 H , 5 H )‐dione was an effective way to design new tetronic acid derivatives as new fungicides.