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Design, Synthesis, Antifungal Activities and 3D-QSAR of New N,N'-Diacylhydrazines Containing 2,4-Dichlorophenoxy Moiety
College of Biology and Environmental Engineering, Zhejiang Shuren University, Hangzhou 310015, China
Institute of Vegetables and Flowers, Chinese Academy of Agricultural Sciences, Beijing 100081, China
College of Chemical Engineering and Materials Science, Zhejiang University of Technology, Hangzhou 310014, China
State-Key Laboratory of Elemento-Organic Chemistry, National Pesticidal Engineering Centre, Nankai University, Tianjin 300071, China
These authors contributed equally to this work.
* Authors to whom correspondence should be addressed.
Received: 1 September 2013; in revised form: 21 October 2013 / Accepted: 23 October 2013 / Published: 1 November 2013
Abstract: A series of new N,N'-diacylhydrazine derivatives were designed and synthesized. Their structures were verified by 1H-NMR, mass spectra (MS) and elemental analysis. The antifungal activities of these N,N'-diacylhydrazines were evaluated. The bioassay results showed that most of these N,N'-diacylhydrazines showed excellent antifungal activities against Cladosporium cucumerinum, Corynespora cassiicola, Sclerotinia sclerotiorum, Erysiphe cichoracearum, and Colletotrichum orbiculare in vivo. The half maximal effective concentration (EC50) of one of the compounds was also determined, and found to be comparable with a commercial drug. To further investigate the structure–activity relationship, comparative molecular field analysis (CoMFA) was performed on the basis of antifungal activity data. Both the steric and electronic field distributions of CoMFA are in good agreement in this study.
Keywords: N,N'-diacylhydrazines; antifungal activity; synthesis; three-dimensional quantitative structure-activity relationships (3D-QSAR)
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Sun, N.-B.; Shi, Y.-X.; Liu, X.-H.; Ma, Y.; Tan, C.-X.; Weng, J.-Q.; Jin, J.-Z.; Li, B.-J. Design, Synthesis, Antifungal Activities and 3D-QSAR of New N,N'-Diacylhydrazines Containing 2,4-Dichlorophenoxy Moiety. Int. J. Mol. Sci. 2013, 14, 21741-21756.
Sun N-B, Shi Y-X, Liu X-H, Ma Y, Tan C-X, Weng J-Q, Jin J-Z, Li B-J. Design, Synthesis, Antifungal Activities and 3D-QSAR of New N,N'-Diacylhydrazines Containing 2,4-Dichlorophenoxy Moiety. International Journal of Molecular Sciences. 2013; 14(11):21741-21756.
Sun, Na-Bo; Shi, Yan-Xia; Liu, Xing-Hai; Ma, Yi; Tan, Cheng-Xia; Weng, Jian-Quan; Jin, Jian-Zhong; Li, Bao-Ju. 2013. "Design, Synthesis, Antifungal Activities and 3D-QSAR of New N,N'-Diacylhydrazines Containing 2,4-Dichlorophenoxy Moiety." Int. J. Mol. Sci. 14, no. 11: 21741-21756.