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Molecules 2015, 20(8), 13740-13752; doi:10.3390/molecules200813740

Discovery of 5-(5,5-Dimethylbutenolide-3-ethylidene)-2-amino-imidazolinone Derivatives as Fungicidal Agents

Department of Applied Chemistry, China Agricultural University, Beijing 100193, China
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Author to whom correspondence should be addressed.
Academic Editor: Jean Jacques Vanden Eynde
Received: 3 July 2015 / Revised: 24 July 2015 / Accepted: 24 July 2015 / Published: 28 July 2015
(This article belongs to the Section Organic Synthesis)
View Full-Text   |   Download PDF [1136 KB, uploaded 28 July 2015]   |  

Abstract

The novel fungicidal agents 5-(5,5-dimethylbutenolide-3-ethylidene)-2-amino-imidazolinone derivatives, were designed and synthesized in moderate to excellent yields in four steps by αa-hydroxyketone and diketene as raw materials and characterized by HR-ESI-MS and 1H-NMR. The preliminary bioassay showed that some of these compounds, such as 4a, 4e and 5g exhibit 94.9%, 92.8% and 81.4% inhibition rates against Sclerotinia scleotiorum at the concentration of 50 µg/mL, respectively. The EC50 values of compounds 4e and 4i were 4.14 and 3.27 µM against Alternaria Solani, and 5g had EC50 value of 3.23 µM against S. scleotiorum. Compounds 4d and 4g displayed 98.0% and 97.8% control of spore germination against Botrytis cinerea at the concentration of 100 µg/mL, respectively. View Full-Text
Keywords: butenolide; 2-aminoimidazolinone; synthesis; fungicidal activity butenolide; 2-aminoimidazolinone; synthesis; fungicidal activity
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Tang, B.; Yang, M.; Zhao, Y.; Kong, L.; Wang, W.; Wang, M. Discovery of 5-(5,5-Dimethylbutenolide-3-ethylidene)-2-amino-imidazolinone Derivatives as Fungicidal Agents. Molecules 2015, 20, 13740-13752.

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