Synthesis and Fungicidal Activity of 3-Acetyl-4-phenyl-1-oxaspiro[4,5]dec-3-en-2-one Derivatives

doi:10.6023/cjoc201804024

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (10): 2767-2774.DOI: 10.6023/cjoc201804024 Previous Articles Next Articles

Notes

3-乙酰基-4-苯基-1-氧代螺[4,5]癸-3-烯-2-酮类衍生物的合成及杀菌活性

关爱莹, 赵宇, 王卫伟, 刘鑫磊, 王明安

中国农业大学理学院应用化学系北京 100193

收稿日期:2018-04-13 修回日期:2018-05-11 发布日期:2018-06-06
通讯作者: 王明安,E-mail:wangma@cau.edu.cn E-mail:wangma@cau.edu.cn
基金资助:
国家自然科学基金（No.21772229）资助项目.

Synthesis and Fungicidal Activity of 3-Acetyl-4-phenyl-1-oxaspiro[4,5]dec-3-en-2-one Derivatives

Guan Aiying, Zhao Yu, Wang Weiwei, Liu Xinlei, Wang Mingan

Department of Applied Chemistry, College of Sciences, China Agricultural University, Beijing 100193

Received:2018-04-13 Revised:2018-05-11 Published:2018-06-06
Contact: 10.6023/cjoc201804024 E-mail:wangma@cau.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21772229).

1. Synthesis and Fungicidal Activity of 3-Acetyl-4-phenyl-1-oxaspiro[4,5]dec-3-en-2-one Derivatives.PDF(1607KB)

Abstract

The diversity-orientied synthesis strategy was utilized to diversely derive from the carbonyl of 3-acetyl-4-phenyl-1-oxaspiro[4,5]dec-3-en-2-one, a series of novel 3-acetyl-4-phenyl-1-oxaspiro[4,5]dec-3-en-2-one derivatives were synthesized. The preliminary in vivo and in vitro bioassay results showed that some compounds exhibited excellent fungicidal activity against phytopathagens, such as 3-allyloxyethyl-4-phenyl-1-oxaspiro[4,5]dec-3-en-2-one (7) had 100% control rates against Pseudoperonospora cubensis and Puccinia polysora at the concentration of 400 μg/mL.

Key words: diversity-orientied synthesis, 3-acetyl-4-phenyl-1-oxaspiro[4,5]dec-3-en-2-one, fungicidal activity, phytopathagen

Cite this article

Guan Aiying, Zhao Yu, Wang Weiwei, Liu Xinlei, Wang Mingan. Synthesis and Fungicidal Activity of 3-Acetyl-4-phenyl-1-oxaspiro[4,5]dec-3-en-2-one Derivatives[J]. Chin. J. Org. Chem., 2018, 38(10): 2767-2774.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Schreiber, S. L. Science 2000, 287, 1964.
[2] Garcia-Castro, M.; Zimmermann, S.; Sankar, M. G.; Kumar, K. Angew. Chem., Int. Ed. 2016, 55, 7586.
[3] Maiti, B.; Chanda, K. RSC Adv. 2016, 6, 50384.
[4] Huang, L.; Ye, L.; Li, X.-H.; Li, Z.-L.; Lin, J.-S.; Liu, X.-Y. Org. Lett. 2016, 18, 5284.
[5] Han, Z.-G.; Miao, C.-B.; Shi, F.; Ma, N.; Zhang, G.; Tu, S.-J. J. Comb. Chem. 2010, 12, 16.
[6] Guan, A. Y.; Liu, C. L.; Yang, X. P.; Dekeyser, M. Chem. Rev. 2014, 114, 7079.
[7] Liu, C. L.; Guan, A. Y.; Yang, J. D.; Chai, B. S.; Li, M.; Li, H. C.; Yang, J. C.; Xie, Y. J. Agric. Food Chem. 2016, 64, 45.
[8] Guan, A. Y.; Liu, C. L.; Sun, X. F.; Xie, Y.; Wang, M. A. Bioorg. Med. Chem. 2016, 24, 342.
[9] Nauen, R.; Jeschke, P.; Velten, R.; Beck, M. E.; Ebbinghaus-Kintscher, U.; Thielert, W.; Wolfel, K.; Haas, M.; Kunz, K.; Raupach, G. Pest. Manage. Sci. 2015, 71, 850.
[10] Jeanmart, S.; Edmunds, A. J. F.; Lamberth, C.; Pouliot, M. Bioorg. Med. Chem. 2016, 24, 317.
[11] Leite, L.; Jansone, D.; Veveris, M.; Cirule, H.; Popelis, J.; Melikyan, G.; Avetisyan, A.; Lukevics, E. Eur. J. Med. Chem. 1999, 34, 859.
[12] Melikyan, G. S.; Hovhannisyan, A. A.; Hayotsyan, S. S. Synth. Commun. 2012, 42, 2267.
[13] Lei, J. P.; Han, J. T.; Xu, Z. H.; Dong, H. B.; Wang, M. A. Chin. J. Org. Chem. 2012, 32, 1993(in Chinese). (雷建平, 韩金涛, 徐志红, 董宏波, 王明安, 有机化学, 2012, 32, 1993.)
[14] Tang, B.; Yang, M. Y.; Zhao, Y.; Kong, L. Q.; Wang, W. W.; Wang, M. A. Molecules 2015, 20, 13740.
[15] Zhao, Y.; Tang, B.; Guan, A. Y.; Wang, W. W.; Zhang, Z. H.; Wang, M. A. Synthesis 2017, 49, 4663.
[16] Tang, B.; Guan, A. Y.; Zhao, Y.; Jiang, J. Z.; Wang, M. A. Chin. J. Chem. 2017, 35, 1133.
[17] Zhao, Y.; Tang, B.; Liu, X. L.; Li, W. Z.; Huang, M. Y.; Wang, M. A. Chin. J. Org. Chem. 2017, 37, 975(in Chinese). (赵宇, 汤博, 刘鑫磊, 李婉祯, 黄铭一, 王明安, 有机化学, 2017, 37, 975.)
[18] Prat, I.; Font, D.; Company, A.; Junge, K.; Ribas, X.; Beller, M.; Costas, M. Adv. Synth. Catal. 2013, 355, 947.
[19] Carceller, G. E.; Salas, S. J.; Alvarez, F. C.; Andreu, A. J. A. WO 2003084984, 2003[Chem. Abstr. 2003, 139, 323795].
[20] Guenther, M.; Lategahn, J.; Juchum, M.; Doering, E.; Keul, M.; Engel, J.; Tumbrink, H. L.; Rauh, D.; Laufer, S. J. Med. Chem. 2017, 60, 5613.
[21] Zhang, C. Y.; Chen, S. C.; Wang, D. Q.; Wang, M. A. Acta Chim. Sinica 2010, 68, 989(in Chinese). (张春艳, 陈守冲, 王道全, 王明安, 化学学报, 2010, 68, 989.)
[22] Zan, N. N.; Wan, F. X.; Wang, S. C.; Zhang, J. H.; Jiang, L. Chin. J. Org. Chem. 2017, 37, 1537(in Chinese). (昝宁宁, 万福贤, 王士春, 张君辉, 姜林, 有机化学, 2017, 37, 1537.)
[23] Yang, Y. Z.; Lin, D. Y.; Fu, C. R.; Zou, X. M. Chin. J. Org. Chem. 2015, 35, 100(in Chinese). (杨亚喆, 林大勇, 傅翠蓉, 邹小毛, 有机化学, 2015, 35, 100.)
[24] Guan, A. Y.; Liu, C. L.; Chen, W.; Yang, F.; Xie. Y.; Zhang, J. B.; Li, Z. N.; Wang, M. A. J. Agric. Food Chem. 2017, 65, 1272.
[25] Guan, A. Y.; Wang, M. A.; Yang, J. L.; Wang, L. Z.; Xie, Y.; Lan, J.; Liu, C. L. J. Agric. Food Chem. 2017, 65, 10829.
[26] Guan, A. Y.; Wang, M. A.; Chen, W.; Yang, F.; Yang, J. L.; Zhao, Y.; Li, Z. N.; Liu, C. L. J. Fluorine Chem. 2017, 201, 49.

3-乙酰基-4-苯基-1-氧代螺[4,5]癸-3-烯-2-酮类衍生物的合成及杀菌活性

Synthesis and Fungicidal Activity of 3-Acetyl-4-phenyl-1-oxaspiro[4,5]dec-3-en-2-one Derivatives

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Penghui Li, Qingyang Xie, Fuxian Wan, Yuanhong Zhang, Lin Jiang. Synthesis and Fungicidal Activity of Novel Substituted Pyrimidine-5-carboxamides Bearing Cyclopropyl Moiety [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 650-656.
[2]	Min Liu, Dongyan Yang, Yumei Xiao, Wangcang Su, Fenghai Zhao, Qin Zhaohai .. Synthesis and Bioactivities of 5-Nitroimino-[1,4-2H]-1,2,4-triazolines as Olefin-Imidacloprid Mimics [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2790-2799.
[3]	Huan Xu, Hongfei Wu, Xiaoming Zhang, Xingxing Lu, Tengda Sun, Yue Qi, Yufan Lin, Xinling Yang, Li Zhang, Yun Ling. Design, Synthesis and Bioactivity of Sulfonyl Hydrazides and Hydrazides Containing Fragment 1,2,3,4-Tetrahydroisoquinoline [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 725-733.
[4]	Changxing Sun, Fuhao Zhang, Huan Zhang, Penghui Li, Lin Jiang. Design, Synthesis, Fungicidal Activity and Molecular Docking Study of Novel 2-(1-Methyl-1H-pyrazol-4-yl)pyrimidine-4-carboxamides [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 229-235.
[5]	Lei Wang, Shujing Yu, Na Yang, Baolei Wang. Studies on the Synthesis and Biological Activities of Novel Dihydroquinazolinone-Containing Caffeine Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 299-307.
[6]	Qian Zhang, Yihao Li, Leichuan Xu, Haoyun Ma, Xiangdong Li, Ming'an Wang. Synthesis and Fungicidal Activity of Novel Butenolide Compounds Containing Oxime Ether Moiety [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2438-2448.
[7]	Changkai Wang, Tengda Sun, Xuebo Zhang, Xinling Yang, Xingxing Lu, Huan Xu, Fasheng Shi, Li Zhang, Yun Ling. Design, Synthesis and Bioactivity of Novel Fluoropyrazole Hydrazides [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1527-1536.
[8]	Weiwei Wang, Yihao Li, Xinlei Liu, Yu Zhao, Mingan Wang. Synthesis and Fungicidal Activity of Novel 3,7-Dimethylocta-2,6-dienamides and 3,7-Dimethyl-6,7-dihydroxyoct-2-enamides [J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3717-3725.
[9]	Can Jin, Xile Deng, Yong Zhou, Xiaomao Zhou. Design, Synthesis, Crystal Structure, and Fungicidal Activity of L-Carvone Derivatives Containing an Oxime Ester Moiety [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 2008-2018.
[10]	Hang Liu, Shuyun Zhang, Huan Li, Yan Zhang, Zhengming Li, Baolei Wang. Synthesis and Biological Activities of Novel 8-((3,4,4-Trifluorobut-3-en-1-yl)thio)-substituted Methylxanthines and Their Derivatives [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 2091-2098.
[11]	Wei Yu, Han Wang, Li-Jing Min, Xue-Wen Hua, Xing-Hai Liu. Synthesis and Fungicidal Activity of Novel Allyl Benzoate Compounds Containing Triazole [J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 826-832.
[12]	Shuyun Zhang, Hang Liu, Lei Wang, Zhengming Li, Baolei Wang. Studies on the Synthesis, Structural Characterization and Biological Activities of Novel Caffeine Derivatives Containing Substituted-Piperazine Moiety [J]. Chinese Journal of Organic Chemistry, 2021, 41(10): 4075-4082.
[13]	Tang Xianjun, Lu Xingliang, Yang Dan, Zhang Min, Xiong Yongtong, Wu Qinglai, Li Junkai. Synthesis and Fungicidal Activities of Novel Tertiary Alcohol Ergosterol Biosynthesis Inhibitors Based on Phenazine-1-carboxylic Acid [J]. Chinese Journal of Organic Chemistry, 2020, 40(8): 2491-2501.
[14]	Wei Kailun, Shi Ruijing, Jiang Lin, Miao Chengxia, Li Ying. Design, Synthesis and Biological Activities Evaluation of N-(Substitutedbenzoyl)-N'-4,7-dimethoxy-[1,2,4]-triazolo[1,5-c]pyrimidine (Thio)ureas [J]. Chinese Journal of Organic Chemistry, 2020, 40(7): 2127-2134.
[15]	Shi Yanhua, Zhang Shuai, Wan Fuxian, Sun Changxing, Jiang Lin. Synthesis, Fungicidal Activity and Molecular Docking Study of Novel N-[2-((Substitutedphenyl)amino)pyridin-3-yl]-pyrimidine-4-carboxamides [J]. Chinese Journal of Organic Chemistry, 2020, 40(7): 1948-1954.