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]
  Bin SUN , Heyan JIANG . Glucose-modified bis-Schiff bases: Synthesis and bio-activities in Alzheimer′s disease therapy. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1338-1350. doi: 10.11862/CJIC.20240428
3. [3]
  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
4. [4]
  Lifang HE , Wenjie TANG , Yaoze LUO , Mingsheng LIANG , Jianxin TANG , Yuxuan WU , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two dialkyltin complexes constructed based on 2, 2′-bipyridin-6, 6′-dicarboxylic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1601-1609. doi: 10.11862/CJIC.20250012
5. [5]
  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
6. [6]
  Lixing ZHANG , Yaowen WANG , Xu HAN , Junhong ZHOU , Jinghui WANG , Liping LI , Guangshe LI . Research progress in the synthesis of fluorine-containing perovskites and their derivatives. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1689-1701. doi: 10.11862/CJIC.20250007
7. [7]
  Ying Chen , Ronghua Yan , Weiyan Yin . Research Progress on the Synthesis of Metal Single-Atom Catalysts and Their Applications in Electrocatalytic Hydrogen Evolution Reactions. University Chemistry, 2025, 40(9): 344-353. doi: 10.12461/PKU.DXHX202503066
8. [8]
  Xinyi Zhang , Kai Ren , Yanning Liu , Zhenyi Gu , Zhixiong Huang , Shuohang Zheng , Xiaotong Wang , Jinzhi Guo , Igor V. Zatovsky , Junming Cao , Xinglong Wu . Progress on Entropy Production Engineering for Electrochemical Catalysis. Acta Physico-Chimica Sinica, 2024, 40(7): 2307057-0. doi: 10.3866/PKU.WHXB202307057
9. [9]
  Lei Feng , Ze-Min Zhu , Ying Yang , Zongbin He , Jiafeng Zou , Man-Bo Li , Yan Zhao , Zhikun Wu . Long-Pursued Structure of Au₂₃(S-Adm)₁₆ and the Unexpected Doping Effects. Acta Physico-Chimica Sinica, 2024, 40(5): 2305029-0. doi: 10.3866/PKU.WHXB202305029
10. [10]
  Chunling Qin , Shuang Chen , Hassanien Gomaa , Mohamed A. Shenashen , Sherif A. El-Safty , Qian Liu , Cuihua An , Xijun Liu , Qibo Deng , Ning Hu . Regulating HER and OER Performances of 2D Materials by the External Physical Fields. Acta Physico-Chimica Sinica, 2024, 40(9): 2307059-0. doi: 10.3866/PKU.WHXB202307059
11. [11]
  Qing ZHANG , Kexin ZHOU , Yanjun GUO , Guangjun CHEN , Bai HE , Bo YU , Songshan JIANG , Guoyuan YUAN , Huidong QIU . Preparation, functional modification, and applications of Fe₃O₄ nanoparticles. Chinese Journal of Inorganic Chemistry, 2026, 42(7): 1383-1411. doi: 10.11862/CJIC.20250344
12. [12]
  Xinran Han , Jiaxin Li , Yuhan Kang , Qiongyou Wu . 虚实融合驱动的绿色杀菌剂苯醚唑酰胺创制实验设计. University Chemistry, 2026, 41(5): 422-429. doi: 10.12461/PKU.DXHX202511113
13. [13]
  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
14. [14]
  Chengyan XU , Jiangnan YU , Yu LI , Xizhen PAN , Yinlin HOU , Wenmin WANG . Synthesis, structure, and bioactivity of a Ho₄ complex bridged by azide group. Chinese Journal of Inorganic Chemistry, 2026, 42(7): 1453-1462. doi: 10.11862/CJIC.20260033
15. [15]
  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
16. [16]
  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
17. [17]
  Qi Zhang , Ziyu Liu , Hongxia Tan , Jun Tong , Dazhen Xu . Research Progress on Direct Synthesis of β-Hydroxy Sulfones via Difunctionalization of Olefins. University Chemistry, 2025, 40(11): 199-209. doi: 10.12461/PKU.DXHX202412064
18. [18]
  Liping GUO . Synthesis and crystal structure characterization of yttrium imido complex: The reactivity of 2-substituted-1-amino-o-carborane with yttrium dialkyl complex. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1409-1415. doi: 10.11862/CJIC.20250065
19. [19]
  Lifang HE , Yaoze LUO , Qiying SHI , Jianxin TANG , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and properties of hydrated tricyclohexyltin theophylline-7-acetic acid complex. Chinese Journal of Inorganic Chemistry, 2026, 42(3): 632-640. doi: 10.11862/CJIC.20250244
20. [20]
  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

Get Citation

PDF

XML

Metrics

PDF Downloads(8)
Abstract views(1498)
HTML views(146)

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