含肟酯基L-香芹酮衍生物的设计、合成、晶体结构及杀菌活性
收稿日期: 2020-10-21
修回日期: 2020-12-11
网络出版日期: 2021-02-22
基金资助
国家自然科学基金(31672056)
Design, Synthesis, Crystal Structure, and Fungicidal Activity of L-Carvone Derivatives Containing an Oxime Ester Moiety
Received date: 2020-10-21
Revised date: 2020-12-11
Online published: 2021-02-22
Supported by
National Natural Science Foundation of China(31672056)
L-香芹酮是一种具有杀菌活性的天然产物, 可用作新型杀菌剂的先导化合物. 因此, 以L-香芹酮为先导化合物,采用活性亚结构拼接法合成了一系列含肟酯的L-香芹酮衍生物. 化合物的结构经过红外, 1H NMR, 13C NMR和高分辨质谱确认. 本研究还测定了这些化合物对油菜菌核真菌、小麦赤霉真菌、水稻稻瘟真菌、西瓜枯萎真菌和水稻纹枯真菌5种植物病原真菌的抑菌活性, 结果表明大部分化合物显示了良好的抑菌活性. 其中(E)-2-甲基-5-(丙-1-烯-2-基)环 己-2-烯-1-酮O-(4-乙基苯甲酰基)肟(4e)对小麦赤霉的杀菌活性最好(EC50=5.07 mg/L), (S,E)-2-甲基-5-(丙-1-烯-2-基)环己-2-烯-1-酮O-(3-甲基苯甲酰基)肟(4b)对油菜菌核的杀菌活性最好(EC50=18.84 mg/L), 均优于对照药剂烯肟菌酯. 因此, L-香芹酮衍生物具有深入研究开发新型杀菌剂的潜力.
金灿 , 邓希乐 , 周勇 , 周小毛 . 含肟酯基L-香芹酮衍生物的设计、合成、晶体结构及杀菌活性[J]. 有机化学, 2021 , 41(5) : 2008 -2018 . DOI: 10.6023/cjoc202010028
L-Carvone is a natural product with fungicidal activity, which can be used as a lead compound for screening new fungicides. A series of L-carvone derivatives containing an oxime ester moiety were synthesized by splicing active substructure strategy with L-carvone as the lead compound. The structures of the L-carvone derivatives were characterized by IR, 1H NMR, 13C NMR and HRMS analyses. The antifungal activities of these compounds were evaluated against five plant pathogenic fungi, namely Sclerotinia sclerotiorum, Fusarium graminearum, Pyricularia grisea, Fusariwn oxysporum and Thanatephorus cucumeris. The results indicated that most of the compounds showed good antifungal activities. Among them, (E)-2- methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one O-(4-ethylbenzoyl)oxime (4e) had the best fungicidal activity against Fusarium graminearum (EC50=5.07 mg/L), and (S,E)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one O-(3-methylbenzoyl)oxime (4b) had the best fungicidal activity against Sclerotinia sclerotiorum, (EC50=18.84 mg/L), which were better than the commercial fungicide enestroburin. Therefore, L-carvone derivatives have the potential to develop new fungicides.
Key words： nature product; L-carvone; synthesis; fungicidal activity
| [1] | (a) Zhang, X. B.; Lei, P.; Sun, T. D.; Jin, X. Y.; Yang, X. L.; Ling, Y. Molecules 2017, 22, 2085. |
| [1] | (b) Deng, X. L.; Zheng, W. N.; Zhou, X. M.; Bai, L. Y. Agronomy 2020, 10, 317. |
| [1] | (c) Cheng, Y.; Xia, X.; Lin, Y.; Cao, H.; Yao, J.; Li, Z. Postharvest Biol. Technol. 2020, 163, 111142. |
| [1] | (d) Deng, X. L.; Zheng, W. N.; Jin, C.; Bai, L. Y. ACS Omega 2020, 5, 23996. |
| [1] | (e) Deng, X. L.; Zhou, X. M.; Wang, Z. Y.; Rui, C. H.; Yang, X. L. Chin. J. Struct. Chem. 2018, 37, 551. |
| [2] | (a) Cheng, Y.; Xia, X.; Lin, Y.; Cao, H.; Yao, J.; Li, Z. Postharvest Biol. Technol. 2020, 163, 111142. |
| [2] | (b) Deng, X. L.; Zhang, L.; Hu, X. P.; Yin, B.; Liang, P.; Yang, X. L. Chin. Chem. Lett. 2016, 27, 251. |
| [2] | (c) Deng, X. L.; Zhao, P. Y.; Zhou, X. M.; Bai, L. Y.; Chem. Eng. J. 2020, 405, 126979. |
| [3] | Zhimo, V. Y.; Biasi, A.; Kumar, A.; Feygenberg, O.; Salim, S.; Vero, S.; Wisniewski, M.; Droby, S. Microorganisms 2020, 8, 428. |
| [4] | Pszczolkowska, A.; Androsiuk, P.; Jastrzebski, J. P.; Paukszto, L.; Okorski, A. Genes 2020, 11, 552. |
| [5] | Akgonullu, S.; Yavuz, H.; Denizli, A. Talanta 2020, 219, 121219. |
| [6] | Jiang, C.; Guo, D.; Li, Z.; Lei, S.; Shi, J.; Shao, D. Appl. Environ. Microbiol. 2019, 85, e01023-19. |
| [7] | (a) Abdelsalam, N. R.; Salem, M. Z. M.; Ali, H. M.; Mackled, M. I.; El-Hefny, M.; Elshikh, M. S.; Hatamleh, A. A. Ind. Crops Prod. 2019, 139, 111515. |
| [7] | (b) Lei, P.; Ding, X. J.; Wu, Y. Y.; Ma, Z. Q. Chin. J. Org. Chem. 2019, 39, 2070. (in Chinese). |
| [7] | (雷鹏, 丁新吉, 吴远勇, 马志卿, 有机化学, 2019, 39, 2070.) |
| [8] | (a) Eldoksch, H. A.; Ayad, F. A.; El-Sebae, A. K. H. Alexandria Sci. Exch. J. 2009, 30, 344. |
| [8] | (b) Shi, Z.; Nie, K. R.; Liu, C.; Zhang, M. Z.; Zhang, W. H. Chin. J. Org. Chem. 2020, 40, 327. (in Chinese). |
| [8] | (施展, 聂克睿, 刘畅, 张明智, 章维华, 有机化学, 2020, 40, 327.) |
| [9] | El-Minshawy, A. M.; Abdelgaleil, S. A. M.; Gadelhak, G. G.; Al-Eryan, M. A.; Rabab, R. A. Environ. Sci. Pollut. Res. 2018, 25, 15671. |
| [10] | Fang, R.; Jiang, C. H.; Wang, X. Y.; Zhang, H. M.; Liu, Z. L.; Zhou, L.; Du, S. S.; Deng, Z. W. Molecules 2010, 15, 9391. |
| [11] | Boonruang, K.; Kerddonfag, N.; Chinsirikul, W.; Mitcham, E. J.; Chonhenchob, V. Food Control 2017, 78, 85. |
| [12] | (a) Fu, L.; Sun, B. X.; Zhai, J. D.; Li, Y. Y.; Liu, X. Q.; Song, R.; Shi, G. Q.; Li, J. N.; Song, Y. X.; Sang, F. Chin. J. Org. Chem. 2020, 40, 201. (in Chinese). |
| [12] | (付林, 孙炳夏, 翟佳黛, 李媛媛, 刘信强, 宋如, 石冠群, 李娇娜, 宋远霞, 桑锋, 有机化学, 2020, 40, 201.) |
| [12] | (b) Tang, X. J.; Lu, X. L.; Yang, D.; Zhang, M.; Xiong, Y. T.; Wu, Q. L.; Li, J. K. Chin. J. Org. Chem. 2020, 40, 2491. (in Chinese). |
| [12] | (汤显军, 鲁星亮, 杨丹, 张敏, 熊永通, 吴清来, 李俊凯, 有机化学, 2020, 40, 2491.) |
| [12] | (c) Deng, X. L.; Zheng, W. N.; Zhan, Q. C.; Deng, Y. N.; Zhou, Y.; Bai, L. Y. Molecules 2020, 25, 4986. |
| [13] | Efsa EFSA J. 2016, 14, 4405. |
| [14] | Ma, H. H.; Huang, Q. T.; Lai, X. Y.; Liu, J.; Zhu, H.; Zhou, Y.; Deng, X. L.; Zhou, X. M. Int. J. Mol. Sci. 2019, 20, 2953. |
| [15] | Boonruang, K.; Kerddonfag, N.; Chinsirikul, W.; Mitcham, E. J.; Chonhenchob, V. Food Control 2017, 78, 85. |
| [16] | du Plooy, W.; Regnier, T.; Combrinck, S. Postharvest Biol. Technol. 2009, 53, 117. |
| [17] | Tsao, R.; Zhou, T. J. Essent. Oil Res. 2000, 12, 113. |
| [18] | Krishnan, K. G.; Sivakumar, R.; Thanikachalam, V. J. Serb. Chem. Soc. 2015, 80, 1101. |
| [19] | Regnier, T.; du Plooy, W.; Combrinck, S.; Botha, B. Postharvest Biol. Technol. 2008, 48, 254. |
| [20] | Abdel-Jalil, R. J.; El Momani, E. Q.; Hamad, M.; Voelter, W.; Mubarak, M. S.; Smith, B. H.; Peters, D. G. Monatsh. Chem. 2010, 141, 251. |
| [21] | Liu, X. H.; Pan, L.; Tan, C. X.; Weng, J. Q.; Wang, B. L.; Li, Z. M. Pestic. Biochem. Physiol. 2011, 101, 143. |
| [22] | Dai, H.; Chen, J.; Hong, Y.; Yuan, B.; Fan, C.; Ma, R.; Liang, Z.; Shi, J. Chin. J. Org. Chem. 2017, 37, 1542. (in Chinese). |
| [22] | (戴红, 陈佳, 洪宇, 袁斌颖, 范崇光, 马瑞媛, 梁志鹏, 石健, 有机化学, 2017, 37, 1542.) |
| [23] | Dai, H.; Zhuang, H.; Shi, L.; Li, G.; Zhang, H.; Fang, Y.; Dai, B. Chin. J. Org. Chem. 2015, 35, 2399. (in Chinese). |
| [23] | (戴红, 庄辉阳, 施磊, 李刚, 张海军, 方源, 戴宝江, 有机化学, 2015, 35, 2399.) |
| [24] | Ouyang, G.; Chen, Z.; Cai, X. J.; Song, B. A.; Bhadury, P. S.; Yang, S.; Jin, L. H.; Xue, W.; Hu, D. Y.; Zeng, S. Bioorg. Med. Chem. 2008, 16, 9699. |
| [25] | Zhao, J.; Bi, Q.; Wu, J.; Lu, F.; Han, X.; Wang, W. J. Phytopathol. 2019, 167, 413. |
| [26] | Fan, F.; Li, N.; Li, G. Q.; Luo, C. X. Plant Dis. 2016, 100, 2414. |
| [27] | Liu, C.; Qin, Z.; Zhou, X.; Xin, M.; Wang, C.; Liu, D.; Li, S. BMC Plant Biol. 2018, 18, 16/1-16/12. |
| [28] | Zhang, R.; Pan, Z.; Wang, X.; Shen, M.; Zhou, J.; Fu, Z.; Jin, Y. Acta Biochim. Biophys. Sin. 2019, 51, 88. |
| [29] | Zhao, L. X.; Jiang, M. J.; Hu, J. J.; Zou, Y. L.; Cheng, Y.; Ren, T.; Gao, S.; Fu, Y.; Ye, F. J. Agric. Food Chem. 2020, 68, 3729. |
| [30] | Yin, L.; Gan, X.; Shi, J.; Zan, N.; Zhang, A.; Ren, X.; Li, M.; Xie, D.; Hu, D.; Song, B. Int. J. Mol. Sci. 2018,19. |
| [31] | (a) Liu, H. Y.; Wang, T. R.; Sheng, G. H.; Qin, J.; Sun, J. Russ. J. Gen. Chem. 2018, 88, 2601. |
| [31] | (b) Deng, X. L.; Xie, J.; Li, Y. Q.; Yuan, D. K.; Hu, X. P.; Zhang, L.; Wang, Q. M.; Chi, M.; Yang, X. L. Chin. Chem. Lett. 2016, 27, 566. |
| [32] | Demidova, Y. S.; Suslov, E. V.; Simakova, O. A.; Volcho, K. P.; Salakhutdinov, N. F.; Simakova, I. L.; Murzin, D. Y. J. Mol. Catal. A: Chem. 2016, 420, 142. |
| [33] | Nilsson, A. M.; Bergstrom, M. A.; Luthman, K.; Nilsson, J. L.; Karlberg, A. T. Food Chem. Toxicol. 2005, 43, 1627. |
| [34] | Al-Wabli, R. I.; Al-Ghamdi, A. R.; Aswathy, S. A. V.; Ghabbour, H. A.; Al-Agamy, M. H.; Hubert Joe, I.; Attia, M. I. Crystals 2019, 9, 82. |
| [35] | (a) Deng, X.L; Jin, C.; Xie, Y.; Gao, J.; Zhou, X. M. Crystals 2020, 10, 713. |
| [35] | (b) Zheng, W. N.; Zhu, Z. Y.; Deng, Y. N.; Wu, Z. C.; Zhou, Y.; Zhou, X. M.; Bai, L. Y.; Deng, X. L. Crystals 2018, 8, 75. |
| [36] | Debona, D.; Rodrigues, F. A.; Rios, J. A.; Nascimento, K. J. T. Phytopathology 2012, 102, 1121. |
| [37] | Khoa, N. D.; Thuy, P. T. H.; Thuy, T. T. T.; Collinge, D. B.; Jorgensen, H. J. L. Phytopathology 2011, 101, 231-40. |
| [38] | Luchesi, L. A.; Paulus, D.; Busso, C.; Frata, M. T.; Oliveira, J. B. Nat. Prod. Res. 2020,1. |
| [39] | Swarnalakshmi, A. S.; Manikandan, V.; Veeramanikandan, V. Asian J. Res. Pharm. Sci. Biotechnol. 2019, 7, 53. |
| [40] | Upadhyay, P.; Tiwari, A. K. Int. J. Curr. Microbiol. Appl. Sci. 2019, 8, 851. |
| [41] | Cai, J.; Zhou, X. M.; Yang, X.; Tang, M. M.; Liao, Q. Y.; Meng, B. Z.; Liao, S.; Chen, G. Y. Bioorg. Chem. 2020, 94, 103362. |
| [42] | Santosh Kumar, S. C.; Kumar, N. V.; Pullabhatla, S.; Bheemanakere, K. B. Synthesis 2014, 46, 1847. |
| [43] | Kunz, P. C.; Wetzel, C.; Spingler, B. Acta Crystallogr. E 2010, 66, i26. |
| [44] | Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. J. Appl. Crystallogr. 2010, 42, 339. |
| [45] | Kratzert, D.; Holstein, J. J.; Krossing, I. J. Appl. Crystallogr. 2015, 48, 933. |
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