Citation: Chen Ying, Li Pu, Chen Mei, Su Shijun, He Jun, Zhang Min, Liu Liwei, Xue Wei. Syntheses and Biological Activities of 1, 4-Pentadien-3-one Derivatives Containing Thioether Triazole Moiety[J]. Chinese Journal of Organic Chemistry, ;2019, 39(10): 2813-2820. doi: 10.6023/cjoc201903048 shu

Syntheses and Biological Activities of 1, 4-Pentadien-3-one Derivatives Containing Thioether Triazole Moiety

State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Bioengineering of Ministry of Education, Center for Research and Development of Fine Chemicals, Guizhou University, Guiyang 550025

Corresponding author: Xue Wei, wxue@gzu.edu.cn
Received Date: 23 March 2019
Revised Date: 18 April 2019
Available Online: 12 October 2019
Fund Project: the National Natural Science Foundation of China 21867003Project supported by the National Key Research and Development Program of China (No. 2017YFD0200506), and the National Natural Science Foundation of China (No. 21867003)the National Key Research and Development Program of China 2017YFD0200506

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A series of novel 1, 4-pentadien-3-one derivatives containing thioether triazole units were synthesized by introducing triazoles bearing thiol groups into the structures of 1, 4-pentadien-3-one. The structures of the newly synthesized compounds were assigned via ¹H NMR, ¹³C NMR and HRMS. Bioassays indicated that some of the compounds showed potential antibacterial activities against X. citri, X. oryzae and R. solanacearum. Among them, compounds F₄, F₆ and F₁₆ demonstrated appreciable inhibitory effect against Xanthomonas axonopodis pv. citri, with half-maximal effective concentration (EC₅₀) values of 16.3, 9.9 and 15.9 μg/mL, which were better than commercial agent bismerthiazol (54.9 μg/mL). Compounds F₁, F₇ and F₁₅ demonstrated appreciable inhibitory effects against Xanthomonas oryzae pv. Oryzae with EC₅₀ values of 9.6, 19.2 and 21.3 μg/mL, which were better than commercial agent bismerthiazol (69.3 μg/mL). Compounds F₃ and F₆also demonstrated appreciable inhibitory effects against Ralstonia solanacearum with EC₅₀ values of 14.2 and 14.5 μg/mL, which were better than commercial agent bismerthiazol (82.6 μg/mL). The possible mechanism of the antibacterial activity of the target compound F₆ against Xanthomonas axonopodis was investigated through scanning electron microscopy.
- 1, 4-pentadien-3-one,
- thioether triazole,
- biological activity,
- scanning electron microscope
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