Citation: Sun Guoshao, Wang Lingna, Jin Shuhui, Dong Yanhong, Lu Huizhe, Zhang Jianjun. Synthesis and Fungicidal Activity of Diamide Compounds Based on the Metabolite of Benalaxyl[J]. Chinese Journal of Organic Chemistry, ;2017, 37(1): 157-165. doi: 10.6023/cjoc201608006 shu

Synthesis and Fungicidal Activity of Diamide Compounds Based on the Metabolite of Benalaxyl

China Agricultural University, Beijing 100193

Corresponding author: Jin Shuhui, shuhuij@cau.edu.cn Zhang Jianjun, zhangjianjun@cau.edu.cn
Received Date: 10 August 2016
Revised Date: 31 August 2016

Fund Project: the National Natural Science Fondation of China 21337005National Science Foundation for Fostering Talents in Basic Research of China J1210064

Figures(3)

Based on benalaxyl pesticide metabolite structure framework, fourteen novel diamide derivatives were synthesized by the reaction of amine and N₂-carboxyacetyl-N₁-(2, 6-dimethylphenyl) alanine methyl ester.Their structures were identified by ¹H NMR, ¹³C NMR spectra and HRMS.The results of bioassay indicated that some compounds possess potential fungicidal activities against 8 kinds of bacteria, and the antibacterial activity of some compounds was better than that of benalaxyl.At a dosage of 5.0×10^-5 g/mL, compound 7d displayed 94.2% antifungal activities against Rhizoctonia solani.Compound 8f displayed 87.1% and 88.9% antifungal activities against Phytophthora capsici and Rhizoctonia solani.
- benalaxyl,
- metabolite,
- diamide,
- synthesis,
- antifungal activity
1. [1]
  Dong, X. X. Med. Philos. 1989, 2, 55(in Chinese).
2. [2]
3. [3]
  Lu, Y. L.; Diao, J. L.; Gu, X.; Zhang, Y. F.; Xu, P.; Wang, P.; Zhou, Z. Q. Chirality 2011, 23, 424. doi: 10.1002/chir.v23.5
4. [4]
  Yaacoby, T.; Hall, J. C.; Stephenson, G. R. Pestic. Biochem. Physiol. 1991, 41, 296. doi: 10.1016/0048-3575(91)90084-Y
5. [5]
  Karmakar, R.; Ramcharan, B.; Gita, K. J. Agric. Food Chem. 2009, 57, 6369. doi: 10.1021/jf9008394
6. [6]
  Zhang, M. M.; Sun, K.; Wu, H. F.; Yang, H.; Zhang, H.; Zhang, J.; Yang, H. X. Agrochemicals 2010, 49, 94(in Chinese).
7. [7]
  Chen, Y. W.; Wan, Y. Y.; Liu, Q. X.; Liu, J. B.; Xiong, L. X.; Yu, S. J.; Li, Z. M. Chin. J. Org. Chem. 2014, 34, 882(in Chinese).
8. [8]
  Liu, Q. X.; Huang, M. Z.; Liu, A. P.; Nie, S. Q.; Lei, M. X.; Ren, Y. G.; Pei, H.; He, L. Y.; Hu, L.; Hu, A. X. Chin. J. Org. Chem. 2014, 34, 118(in Chinese). doi: 10.6023/cjoc201307017
9. [9]
  Xie, F.; Liu, T. T.; Yang, G.; Yuan, J.; Kong, X. L.; Xu, T. M.; Tan, C. X. Chin. J. Org. Chem. 2013, 33, 2596(in Chinese). doi: 10.6023/cjoc201307006
10. [10]
  Ning, L. H.; Peng, H.; Xu, H. Y.; He, H. W. Chin. J. Pestic. Sci. 2004, 6, 74(in Chinese).
11. [11]
  Liu, T. T.; Nie, Y.; Zhong, L. K.; Huang, H. Y.; Hu. W. Q.; Xu, T. M.; Tan, C. X. Chin. J. Org. Chem. 2015, 35, 422(in Chinese). doi: 10.6023/cjoc201406017
12. [12]
  Chen, Z. X.; Wei, M. X.; Li, X. Q.; Li, T. C.; Zhou, X. Z. Chin. J. Org. Chem. 2015, 35, 835(in Chinese). doi: 10.6023/cjoc201410013
13. [13]
  Zhang, D. Q.; Xu, G. F.; Liu, Y. H.; Wang, D. Q.; Yang, X. L.; Yuan, D. K. Chin. J. Org. Chem. 2015, 35, 2191(in Chinese). doi: 10.6023/cjoc201505026
14. [14]
  Nie, Y.; Xu, T. M.; Zhong, L. K.; Kong, X. Y.; Shi, J. J.; Liu, X. H.; Kong, X. L.; Ji, W. J.; Tan, C. X. Chin. J. Org. Chem. 2015, 35, 2218(in Chinese). doi: 10.6023/cjoc201504025
15. [15]
  Zhang, H.; Liu, R. Q.; Li, Q. B.; Li, Q. Y.; Chen, Y. H.; Liu, K. C.; Liu, S. Z. Chin. J. Org. Chem. 2015, 35, 1506(in Chinese). doi: 10.6023/cjoc201501040
16. [16]
  Li, X. S. Hunan Chem. 1994, (3), 31(in Chinese).
17. [17]
  Gao, Y. X.; Chen, J. H.; Liu, C.; Lv, X. T.; Li, J. Z.; Guo, B. Y. J. Agric. Food Chem. 2013, 61, 9045 doi: 10.1021/jf4020125
18. [18]
  Paolo, C.; Marco, M.; Filippo, M. P. J. Chromatogr. 1987, 391, 334. doi: 10.1016/S0021-9673(01)94334-1
19. [19]
  Liu, M. K.; Liu, D. H.; Xu, Y. G.; Jing, X.; Zhou, Z. Q.; Wang, P. J. Agric. Food Chem. 2015, 61, 5205.
20. [20]
  Zhang, X.; Zhang, Y. J.; Chen, Y.; Zhou, M. G. Chin. J. Pestic. Sci. 2008, 10, 41(in Chinese).
21. [21]
  Freeman, G. A.; Andrews Ⅲ, C. W.; Hopkins, A. L.; Lowell, G. S.; Schaller, L. T.; Cowan, J. R.; Gonzales, S. S.; Koszalka, G. W.; Hazen, R. J.; Boone, L. R.; Ferris, R. G.; Creech, K. L.; Roberts, G. B.; Short, S. A.; Weaver, K.; Reynolds, D. J.; Milton, J.; Ren, J. S.; Stuart, D. I.; Stammers, D. K.; Chan, J. H. J. Med. Chem. 2004, 47, 5923. doi: 10.1021/jm040072r
22. [22]
  Noboru, S.; Toshio, U. Bull. Fac. Agric., Meiji Univ. 1986, 47.
23. [23]
  Renhowe, P. A.; Pecchi, S.; Shafer, C. M.; Machajewski, T. D.; Jazan, E. M.; Taylor, C.; Antonios-McCrea, W.; McBride, C. M.; Frazier, K.; Wiesmann, M.; Lapointe, G. R.; Feucht, P. H.; Warne, R. L.; Heise, C. C.; Menezes, D.; Aardalen, K.; Ye, H. L.; He, M.; Le, V.; Vora, J.; Jansen, J. M.; Wernette-Hammond, M. E.; Harris, A. L. J. Med. Chem. 2009, 52, 278. doi: 10.1021/jm800790t
24. [24]
  Tamura, H.; Matsuda, T.; Komiyama, T. JP 51126127, 1976[Chem. Abstr. 1977, 87, 9352].
25. [25]
  Goodfellow, V. S.; Settineri, M.; Lawton, R. G. Biochemistry 1989, 28, 6346. doi: 10.1021/bi00441a030
26. [26]
  Ramana Reddy, M. V.; Akula, B.; Cosenza, S. C.; Athuluridivakar, S.; Mallireddigari, M. R.; Pallela, V. R.; Billa, V. K.; Subbaiah, D. R. C. V.; Bharathi, E. V.; Vasquez-Del Carpio, R.; Padgaonkar, A.; Baker, S. J.; Reddy, E. P. J. Med. Chem. 2014, 57, 578. doi: 10.1021/jm401073p
27. [27]
  Bruge, D.; Buchstaller, H. P.; Wiesner, M.; Finsinger, D.; Baumgarth, M.; Sirrenberg, C.; Zenke, F.; Amendt, C.; Grell, M. WO 2005005389, 2005[Chem. Abstr. 2005, 142, 134581].
28. [28]
  Anandan, S. K.; Ward, J. S.; Brokx, R. D.; Bray, M. R.; Patel, D. V.; Xiao, X. X. Bioorg. Med. Chem. Lett. 2005, 15, 1969. doi: 10.1016/j.bmcl.2005.02.075
29. [29]
  Pradhan, A.; Pradhan, V.; Jolly, V. S. Orient. J. Chem. 1994, 10, 73.
30. [30]
  Veronese, A. C.; Callegari, R.; Morelli, C. F. Tetrahedron 1995, 51, 12277. doi: 10.1016/0040-4020(95)00773-2
31. [31]
  Pareek, A. K.; Joseph, P. E.; SethbDaya, S. Orient. J. Chem. 2009, 25, 681.
32. [32]
  Fache, F.; Valot, F.; Milenkovic, A.; Lemaire, M. Tetrahedron 1996, 52, 9777. doi: 10.1016/0040-4020(96)00503-0
33. [33]
  Zheng, L. Y.; Zhang, S. Q.; Zhao, L. F.; Zhu, G. S.; Yang, X. Y.; Gao, G.; Cao, S. G. J. Mol. Catal. B:Enzym. 2006, 38, 119. doi: 10.1016/j.molcatb.2005.12.003
1. [1]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
2. [2]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
3. [3]
  Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
4. [4]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
5. [5]
  Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003
6. [6]
  Yongpo Zhang , Xinfeng Li , Yafei Song , Mengyao Sun , Congcong Yin , Chunyan Gao , Jinzhong Zhao . Synthesis of Chlorine-Bridged Binuclear Cu(I) Complexes Based on Conjugation-Driven Cu(II) Oxidized Secondary Amines. University Chemistry, 2024, 39(5): 44-51. doi: 10.3866/PKU.DXHX202309092
7. [7]
  Hong RAO , Yang HU , Yicong MA , Chunxin LÜ , Wei ZHONG , Lihua DU . Synthesis and in vitro anticancer activity of phenanthroline-functionalized nitrogen heterocyclic carbene homo- and heterobimetallic silver/gold complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2429-2437. doi: 10.11862/CJIC.20240275
8. [8]
  Linjie ZHU , Xufeng LIU . Synthesis, characterization and electrocatalytic hydrogen evolution of two di-iron complexes containing a phosphine ligand with a pendant amine. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 939-947. doi: 10.11862/CJIC.20240416
9. [9]
  Caixia Lin , Zhaojiang Shi , Yi Yu , Jianfeng Yan , Keyin Ye , Yaofeng Yuan . Ideological and Political Design for the Electrochemical Synthesis of Benzoxathiazine Dioxide Experiment. University Chemistry, 2024, 39(2): 61-66. doi: 10.3866/PKU.DXHX202309005
10. [10]
  Tao Cao , Fang Fang , Nianguang Li , Yinan Zhang , Qichen Zhan . Green Synthesis of p-Hydroxybenzonitrile Catalyzed by Spinach Extracts under Red-Light Irradiation: Research and Exploration of Innovative Experiments for Pharmacy Undergraduates. University Chemistry, 2024, 39(5): 63-69. doi: 10.3866/PKU.DXHX202309098
11. [11]
  Yuena Yu , Fang Fang . Microwave-Assisted Synthesis of Safinamide Methanesulfonate. University Chemistry, 2024, 39(11): 210-216. doi: 10.3866/PKU.DXHX202401076
12. [12]
  Xinghai Li , Zhisen Wu , Lijing Zhang , Shengyang Tao . Machine Learning Enables the Prediction of Amide Bond Synthesis Based on Small Datasets. Acta Physico-Chimica Sinica, 2025, 41(2): 100010-. doi: 10.3866/PKU.WHXB202309041
13. [13]
  Yingchun ZHANG , Yiwei SHI , Ruijie YANG , Xin WANG , Zhiguo SONG , Min WANG . Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078
14. [14]
  Cheng Zheng , Shiying Zheng , Yanping Zhang , Shoutian Zheng , Qiaohua Wei . Synthesis, Copper Content Analysis, and Luminescent Performance Study of Binuclear Copper (I) Complexes with Isomeric Luminescence Shift: A Comprehensive Chemical Experiment Recommendation. University Chemistry, 2024, 39(7): 322-329. doi: 10.3866/PKU.DXHX202310131
15. [15]
  Hao Wu , Zhen Liu , Dachang Bai . ¹H NMR Spectrum of Amide Compounds. University Chemistry, 2024, 39(3): 231-238. doi: 10.3866/PKU.DXHX202309020
16. [16]
  Ling Liu , Haibin Wang , Genrong Qiang . Curriculum Ideological and Political Design for the Comprehensive Preparation Experiment of Ethyl Benzoate Synthesized from Benzyl Alcohol. University Chemistry, 2024, 39(2): 94-98. doi: 10.3866/PKU.DXHX202304080
17. [17]
  Feng Sha , Xinyan Wu , Ping Hu , Wenqing Zhang , Xiaoyang Luan , Yunfei Ma . Design of Course Ideology and Politics for the Comprehensive Organic Synthesis Experiment of Benzocaine. University Chemistry, 2024, 39(2): 110-115. doi: 10.3866/PKU.DXHX202307082
18. [18]
  Wanmin Cheng , Juan Du , Peiwen Liu , Yiyun Jiang , Hong Jiang . Photoinitiated Grignard Reagent Synthesis and Experimental Improvement in Triphenylmethanol Preparation. University Chemistry, 2024, 39(5): 238-242. doi: 10.3866/PKU.DXHX202311066
19. [19]
  Liangzhen Hu , Li Ni , Ziyi Liu , Xiaohui Zhang , Bo Qin , Yan Xiong . A Green Chemistry Experiment on Electrochemical Synthesis of Benzophenone. University Chemistry, 2024, 39(6): 350-356. doi: 10.3866/PKU.DXHX202312001
20. [20]
  Ping Song , Nan Zhang , Jie Wang , Rui Yan , Zhiqiang Wang , Yingxue Jin . Experimental Teaching Design on Synthesis and Antitumor Activity Study of Cu-Pyropheophorbide-a Methyl Ester. University Chemistry, 2024, 39(6): 278-286. doi: 10.3866/PKU.DXHX202310087

Get Citation

PDF

XML

Metrics

PDF Downloads(6)
Abstract views(899)
HTML views(88)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142