Synthesis and Antifungal Activity of Novel Furan-2,4-dione Derivatives Containing Substituted Phenylhydrazine Moiety
Synthesis and Antifungal Activity of Novel Furan-2,4-dione Derivatives Containing Substituted Phenylhydrazine Moiety
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DOI：
10.1002/jccs.201400463
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发表时间：
2015-06
影响因子：
1.8
通讯作者：
Hu Ying;Zhang Lizhi;Z. Ren;Zhao Zheng;Wenqing Xu;Chunlong Yang
中科院分区：
文献类型：
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作者：
Hu Ying;Zhang Lizhi;Z. Ren;Zhao Zheng;Wenqing Xu;Chunlong Yang
以4-氯乙酰乙酸乙酯为起始原料，设计合成了一系列3-（2-（取代苯基）肼基亚甲基）呋喃-2，4（3 H，5 H）-二酮化合物。其结构经FT-IR、1H NMR、13 C NMR、EI-MS和元素分析确证。生物活性测定结果表明，这些化合物对小麦赤霉病菌、番茄灰霉病菌、小麦丝核菌和辣椒炭疽菌具有显著的抑菌活性。化合物3-（2-（4-溴苯基）肼基亚甲基）呋喃-2，4（3 H，5 H）-二酮（5g）对番茄灰霉病菌具有良好的生物活性，其EC 50值为0.18 μg/mL，明显低于商品杀菌剂腐霉利的0.24 μg/mL。结果表明，在呋喃-2，4（3 H，5 H）-二酮的3位引入卤代苯肼是设计新型特窗酸类杀菌剂的有效途径。
A series of novel 3-(2-(substituted phenyl)hydrazinylmethylidene)furan-2,4(3H,5H)-diones were designed and synthesized with ethyl 4-chloroacetoacetate as the starting material. Their structures were confirmed by FT-IR, 1H NMR, 13C 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(3H,5H)-dione (5g) had excellent bioactivity against Botrytis cinerea with an EC50 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(3H, 5H)-dione was an effective way to design new tetronic acid derivatives as new fungicides.