Citation: Li Changsheng, Zou Yulong, Jia Changqing, Qin Zhaohai, Ma Yongqiang. Synthesis and Fungicidal Activity of Bridging Ligand Compounds of Azo with 1, 3, 5-Substitued Triazole[J]. Chinese Journal of Organic Chemistry, ;2018, 38(6): 1500-1506. doi: 10.6023/cjoc201710011 shu

Synthesis and Fungicidal Activity of Bridging Ligand Compounds of Azo with 1, 3, 5-Substitued Triazole

a.
College of Sciences, China Agricultural University, Beijing 100193
b.
Mudanjiang Medical University Affiliated Hongqi Hospital, Mudanjiang 554300
c.
Tongren Polytechnic College, Tongren 554300

Corresponding author: Ma Yongqiang, mayongqiang@cau.edu.cn
Received Date: 9 October 2017
Revised Date: 29 January 2018
Available Online: 6 June 2018
Fund Project: Project supported by the National Natural Science Foundation of China (No. 31272076) and the National Key Technology Support Program of China(No. 2015BAK45B01)the National Key Technology Support Program of China 2015BAK45B01the National Natural Science Foundation of China 31272076

Figures(2)

Sixteen bridging ligand compounds of azo with 1, 3, 5-substitued triazole had been synthesized from 1, 3, 5-trisub-stituted-1, 2, 4-triazoles by the oxidative coupling reaction using potassium permanganate or sodium dichloroisocyamirate as the oxidant. The structures of the target compounds were determined by ¹H NMR, ¹³C NMR, IR, MS, HRMS and X-ray diffraction. They were tested for in vitro fungicidal activities by the mycelium growth rate method. The results indicated that most of the title compounds had a certain inhibitory activity at the concentration of 50 μg/mL. Especially, the inhibition rate of 1, 2-bis(1-butyl-3-(2-chlorophenyl)-1H-1, 2, 4-triazol-5-yl)diazene (3h) and 1, 2-bis(3-(4-chlorophenyl)-1-propyl-1H-1, 2, 4-triazol-5-yl)diazene (3k) were close to that of triadimefon when against Pythium aphanidermatum, while the inhibition rate of 1, 2-bis(3-(2-chlorophenyl)-1-propyl-1H-1, 2, 4-triazol-5-yl)diazene (3g) was higher than that of riadimefon. The reactions of these compounds were simple and mild, which was of reference significance to the creation and synthesis of new pesticides.
- triazole,
- azo compounds,
- oxidative coupling,
- fungicidal activities
1. [1]
  Stefaskań, J.; Struga, M.; Tyski, S.; Kossakowski, J.; Dobosz, M. Pol. J. Microbiol. 2008, 57, 179.
2. [2]
  Wang, B.-L.; Shi, Y.-X.; Ma, Y.; Liu, X.-H.; Li, Y.-H.; Song. H.-B.; Li, B.-J.; Li, Z.-M. J. Agric. Food Chem. 2010, 58, 551.
3. [3]
  Plech, T.; Wujec, M.; Kosikowska, U.; Malm, A.; Kaproń, B. Eur. J. Med. Chem. 2012, 47, 580. doi: 10.1016/j.ejmech.2011.10.055
4. [4]
  Barbuceanu, S.-F.; Saramet, G.; Almajan, G. L.; Draghici, C.; Barbuceanu, F.; Bancescu, G. Eur. J. Med. Chem. 2012, 49, 417. doi: 10.1016/j.ejmech.2012.01.031
5. [5]
  Lin, X.-F.; Tan, Z.; Liu, Y.; He, Y.-J.; Bao, X.-P. Chin. J. Org. Chem. 2013, 33, 353(in Chinese).
6. [6]
  Liu, J.-H.; Liu, Y.; Jian, J.-Y.; Bao, X.-P. Chin. J. Org. Chem. 2013, 33, 370(in Chinese).
7. [7]
  Bao, X.-P.; Lin, X.-F.; Jian, J.-Y.; Zhang, F.; Zou, L.-B. Chin. J. Org. Chem. 2013, 33, 995(in Chinese).
8. [8]
  Wang, B.-L.; Zhang, Y.; Liu, X.-H.; Zhang, L.-Y.; Zhan, Y.-Z.; Zhang, X.; Wang, L.-Z.; Li, Y.-H.; Li, Z.-M. Phosphorus, Sulfur Silicon Relat. Elem. 2017, 192, 34 doi: 10.1080/10426507.2016.1223077
9. [9]
  Fan, Z.-J; Yang, Z.-K.; Zhang, H.-K.; Mi, N.; Wang, H.; Cai, F.; Zou, X.; Zheng, Q.-X.; Song, H. J. Agric. Food Chem. 2010, 58, 2630. doi: 10.1021/jf9029628
10. [10]
  Song, X.-J.; Wang, S.; Tan, X.-H.; Wang, Z.-Y.; Wang, Y.-G. Chin. J. Org. Chem. 2007, 27, 72(in Chinese). doi: 10.3321/j.issn:0253-2786.2007.01.008
11. [11]
  Deng, X.-Q.; Song, M.-X.; Wei, C.-X.; Li, F.-N.; Quan, Z. S. Med. Chem. 2010, 6, 313. doi: 10.2174/157340610793358855
12. [12]
  Drabent, K.; Bialonska, A.; Ciunik, Z. Inorg. Chem. Commun. 2004, 7, 224. doi: 10.1016/j.inoche.2003.11.008
13. [13]
  Pan, L.; Chen, Y.-W.; Liu, Z.; Li, Y.-H.; Li, Z.-M. Chin. J. Org. Chem. 2013, 33, 542(in Chinese).
14. [14]
  Sumangala, V.; Poojary, B.; Chidananda, N.; Arulmoli, T.; Shenoy, S. Eur. J. Med. Chem. 2012, 54, 59. doi: 10.1016/j.ejmech.2012.04.024
15. [15]
  Mavrova, A. T.; Wesselinova, D.; Tsenov, Y. A.; Denkova, P. Eur. J. Med. Chem. 2009, 44, 63. doi: 10.1016/j.ejmech.2008.03.006
16. [16]
  Abdel-Wahab, B. F.; Abdel-Latif, E.; Mohamed, H. A.; Awad, G. E. A. Eur. J. Med. Chem. 2012, 52, 263. doi: 10.1016/j.ejmech.2012.03.023
17. [17]
  Almasirad, S. A.; Tabatabai, M.; Faizi, A.; Kebriaeezadeh, N.; Mehrabi, A.; Dalvandi, A. S. Bioorg. Med. Chem. Lett. 2004, 14, 6057. doi: 10.1016/j.bmcl.2004.09.072
18. [18]
  Amir, M.; Shikha, K. Eur. J. Med. Chem. 2004, 39, 535 doi: 10.1016/j.ejmech.2004.02.008
19. [19]
  Il'inykh, E.-S.; Kim, D.-G. Chem. Heterocycl. Compd. 2011, 47, 636. doi: 10.1007/s10593-011-0809-x
20. [20]
  Mioc, M.; Soica, C.; Bercean, V.; Avram, S.; Balan-Porcarasu, M.; Coricovac, D.; Ghiulai, R.; Muntean, D.; Andrica, F.; Dehelean, C.; Spandidos, D.-A.; Tsatsakis, A.-M.; Kurunczi, L. Int. J. Oncol. 2017, 50, 1175. doi: 10.3892/ijo.2017.3912
21. [21]
  Tumosienė, I.; Jonuškienė, I.; Kantminienė, K.; Beresnevičius, Z.-J. Monatsh. Chem. 2014, 145, 319. doi: 10.1007/s00706-013-1096-2
22. [22]
  Xu, H.; Zeng, X.-W. Bioorg. Med. Chem. Lett. 2010, 20, 4193. doi: 10.1016/j.bmcl.2010.05.048
23. [23]
  Sayed, A. Z.; Aboul-Fetouh, M. S.; Nassar, H. S. J. Mol. Struct. 2012, 1010, 146. doi: 10.1016/j.molstruc.2011.11.046
24. [24]
  Patel, N. B.; Sharma, R. D. Synth. Commun. 2013, 43, 1250. doi: 10.1080/00397911.2011.630771
25. [25]
  Kuznetsov, D. N.; Ruchkina, A. G.; Kobrakov, K. I. Chem. Heterocycl. Compd. 2011, 47, 441. doi: 10.1007/s10593-011-0778-0
26. [26]
  Subramanyam, S.; Raja, S.; Jayaveera, K. N. J. Pharm. Chem. 2012, 6, 10.
27. [27]
  Li, Z.; Qian, X.-H.; Ye, Z.-J.; Xu, X.-Y.; Shao, X.-S.; Tao, L.-M.; Song, G.-H.; Xu, Z.-P. CN 102464653, 2012.
28. [28]
  Elsharabasy, F. S.; Gomha, S. M.; Farghaly, T. A.; Elzahabi, H. S. A. Molecules 2017, 22, 319. doi: 10.3390/molecules22020319
29. [29]
  Qin, Z.-H.; Ma, Y.-Q.; Su, W.-C.; Wang, L.; Zhang, Z.; Zhao, B.-B.; Fang, J.-S. CN 101821232, 2010.
30. [30]
  Qin, Z.-H.; Mu, C.-W.; Li, N.; Fu, B.; Zhang, S.-S.; Xiao, Y.-M. CN 1939128, 2006.
31. [31]
  Su, W.-C.; Zhou, Y.-H.; Ma, Y.-Q.; Wang, L.; Zhang, Z.; Rui, C.-H.; Duan, H.-X.; Qin, Z.-H. J. Agric. Food Chem. 2012, 60, 5028. doi: 10.1021/jf300616x
32. [32]
  Qin, Z.-H.; Ma, Y.-Q.; Zhou, Y.-H.; Xu, Y.; Jia, C.-Q.; Zhou, Z.-Y.; Yang, D.-Y. CN 102863360, 2013.
33. [33]
  Qin, Z.-H.; Ma, Y.-Q.; Su, W.-C.; Zhao, B.-B.; Fang, J.-S. WO 2013003977, 2013.
34. [34]
  Jia, C.-Q.; Yang, D.-Y.; Che, C.-L.; Ma, Y.-Q.; Rui, C.-H.; Yan, X.-J.; Qin, Z.-H. Chem. J. Chin. Univ. 2016, 37, 892(in Chinese).
35. [35]
  Jia, C.-Q.; Su, W.-C.; Xu, Y.-J.; Liu, J.-P.; Qin, Z.-H. Chin. J. Org. Chem. 2016, 36, 830(in Chinese).
36. [36]
  Venugopal, T.; Jean'ne, M. S. J. Am. Chem. Soc. 2011, 133, 19982. doi: 10.1021/ja208990z
37. [37]
  Li, Y.-C.; Qi, C.; Li, S.-H.; Zhang, H.-J.; Sun, C.-H.; Yu, Y.-Z.; Pang, S.-P. J. Am. Chem. Soc. 2010, 132, 12172. doi: 10.1021/ja103525v
38. [38]
  Allen, F. H.; Kennard, O.; Watson, D. G.; Brammer, L.; Orpen, A. G.; Taylor, R. J. Chem. Soc., Perkin Trans. 21987, S1.
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