Citation: Gao-Fei Xu, Xin-Ling Yang, Peng Lei, Xi-li Liu, Xue-Bo Zhang, Yun Ling. Synthesis and fungicidal activity study of novel daphneolone analogs with 2, 6-dimethylmorpholine[J]. Chinese Chemical Letters, ;2016, 27(4): 555-558. shu

Synthesis and fungicidal activity study of novel daphneolone analogs with 2, 6-dimethylmorpholine

a Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China;
b Department of Plant Pathology, College of Agronomy and Biotechnology, China Agricultural University, Beijing 100193, China

Received Date: 5 November 2015
Revised Date: 3 December 2015

Fund Project: This work was financially supported by the National Natural Science Foundation of China (No. 21272266) and the National High Technology Research and Development Program of China (No. 2011AA10A202).

A series of novel daphneolone analogswas designed and synthesized on the basis of natural product 1, 5-diphenyl-2-penten-1-one (I) from Stellera chamaejasme L. as lead compound, whereby 2, 6-dimethylmorpholine moiety was introduced to replace 1-phenyl group. Their structures were confirmed by IR, ¹H NMR, and HRMS (ESI) or elemental analysis, ¹³C NMR for some representative compounds. The two isomers of target compounds were separated and identified by NOESY technique and chemical method. All of the synthesized compounds have been evaluated for anti-plant pathogenic fungi activities. The results showed that some compounds exhibited moderate to good antifungal activities against tested fungi at the concentration of 50 mg/L. Among them, compound 7d, with a 4-bromine-substituted phenyl group and cis-2, 6-dimethylmorpholine moiety, displayed best activity with an EC₅₀ of 23.87 μmol/L against Valsa mali, superior to lead compound I. In addition, preliminary structure-activity relationship analysis indicated that, between two isomers of target compounds, the antifungal activities of the isomer with cis-2, 6-dimethylmorpholine were better than the trans-isomer.
- Daphneolone analogs,
- 2, 6-Dimethylmorpholine,
- Stellera chamaejasme L.,
- Synthesis,
- Fungicidal activity
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