Citation: Wang Xiaobin, Fu Xincan, Chen Min, Wang An, Yan Jinghua, Mei Yudong, Wang Mengqi, Yang Chunlong. Novel 1, 3, 5-thiadiazine-2-thione derivatives containing a hydrazide moiety: Design, synthesis and bioactive evaluation against phytopathogenic fungi in vitro and in vivo[J]. Chinese Chemical Letters, ;2019, 30(7): 1419-1422. doi: 10.1016/j.cclet.2019.03.038 shu

Novel 1, 3, 5-thiadiazine-2-thione derivatives containing a hydrazide moiety: Design, synthesis and bioactive evaluation against phytopathogenic fungi in vitro and in vivo

Wang Xiaobin ^a,b ,
Fu Xincan ^a ,
Chen Min ^a,b ,
Wang An ^a ,
Yan Jinghua ^a ,
Mei Yudong ^a ,
Wang Mengqi ^a ,
Yang Chunlong ^a,b,*,

a.
Jiangsu Key Laboratory of Pesticide Science, Nanjing Agricultural University, Nanjing 210095, China
b.
Department of Chemistry, College of Sciences, Nanjing Agricultural University, Nanjing 210095, China

ycl@njau.edu.cn

Received Date: 20 February 2019
Revised Date: 20 March 2019
Accepted Date: 21 March 2019
Available Online: 22 July 2019

Figures(3)

A series of novel 1, 3, 5-thiadiazine-2-thione derivatives bearing a hydrazide moiety were designed, synthesized and evaluated for their antifungal activities against Rhizoctonia solani (Rs), Fusarium graminearum (Fg), Botrytis cinerea (Bc) and Colletotrichum capsici (Cc). The in vitro antifungal bioassays indicated that most of title compounds displayed good selectivity and specificity aganist Rs relative to Fg, Bc and Cc. Strikingly, the title compound N'-(4-chlorophenyl)-2-(5-phenyl-6-thioxo-1, 3, 5-thiadiazinan-3-yl)acethydrazide (5b) obviously inhibited the Rs growth in vitro with the EC₅₀ value of 0.24μg/mL, which is approximately 2-folds more effective than the commercialized fungicide carbendazim (0.55 μg/mL). The in vivo anti-Rs effects of title compound 5b were further evaluated on rice leaves with control efficacies of 98.58% at 200 μg/mL and 61.27% at 100 μg/mL. The above researches provide a significant reference for the further structural optimization of 1, 3, 5-thiadiazine-2-thione derivatives bearing a hydrazide moiety as potential fungicides.
- 1, 3, 5-Thiadiazine-2-thione,
- Hydrazide,
- Crop protection,
- Antifungal activity,
- Rhizoctonia solani
1. [1]
  R.N. Strange, P.R. Scott, Annu. Rev. Phytopathol. 43(2005) 83-116. doi: 10.1146/annurev.phyto.43.113004.133839
2. [2]
  B. Song, Pestic. Biochem. Physiol. 147(2018) 1-2. doi: 10.1016/j.pestbp.2018.03.020
3. [3]
  K. Kazan, D.M. Gardiner, J.M. Manners, Mol. Plant Pathol. 13(2012) 399-413. doi: 10.1111/j.1364-3703.2011.00762.x
4. [4]
  Y. Zhang, Y.Z. Zhang, Y. Ma, et al., Chin. Chem. Lett. 29(2018) 441-446. doi: 10.1016/j.cclet.2017.08.035
5. [5]
  X. Wang, Z. Ren, M. Wang, et al., Chem. Cent. J. 83(2018) 1-12.
6. [6]
  T.C. Sparks, B.A. Lorsbach, Pest Manage. Sci. 73(2017) 672-677. doi: 10.1002/ps.4457
7. [7]
  L.S. Jackson, J. Agric. Food Chem. 57(2009) 8161-8170. doi: 10.1021/jf900628u
8. [8]
  J.N. Seiber, L.A. Kleinschmidt, J. Agric. Food Chem. 59(2011) 7536-7543. doi: 10.1021/jf103902t
9. [9]
  X. Qian, P.W. Lee, S. Cao, J. Agric. Food Chem. 58(2010) 2613-2623. doi: 10.1021/jf904098w
10. [10]
  F. Yu, A. Guan, M. Li, et al., Chin. Chem. Lett. 29(2018) 915-918. doi: 10.1016/j.cclet.2018.01.050
11. [11]
  A.N. El-Shorbagi, Eur. J. Med. Chem. 29(1994) 11-15. doi: 10.1016/0223-5234(94)90120-1
12. [12]
  T. Aboul-Fadl, A.N. El-Shorbagi, Eur. J. Med. Chem. 31(1996) 165-169. doi: 10.1016/0223-5234(96)80450-8
13. [13]
  A.N. El-Shorbagi, M. El-Naggar, H. Tarazi, et al., Med. Chem. Res. 27(2018) 1103-1110. doi: 10.1007/s00044-018-2133-9
14. [14]
  A.N. El-Shorbagi, Arch. Pharm. 333(2000) 281-286.
15. [15]
  M.H. Semreen, A.N. El-Shorbagi, T.H. Al-Tel, et al., Med. Chem. 6(2010) 144-149. doi: 10.2174/1573406411006030144
16. [16]
  C.B. Vicentini, G. Forlani, M. Manfrini, et al., J. Agric. Food Chem. 50(2002) 4839-4845. doi: 10.1021/jf0202436
17. [17]
  N. Arshad, J. Hashim, Irfanullah, et al., Bioorg. Med. Chem. Lett. 28(2018) 3251-3254. doi: 10.1016/j.bmcl.2018.07.045
18. [18]
  J.Coro, R. Atherton, S.Little, et al., Bioorg. Med. Chem.Lett.16(2006) 1312-1315. doi: 10.1016/j.bmcl.2005.11.060
19. [19]
  D.Katiyar, V.K.Tiwari, R.P.Tripathi, et al., Bioorg.Med.Chem.11(2003)4369-4375. doi: 10.1016/S0968-0896(03)00480-2
20. [20]
  J. Coro, R. Perez, H. Rodriguez, et al., Bioorg. Med. Chem.13(2005) 3413-3421. doi: 10.1016/j.bmc.2005.03.009
21. [21]
  X. Ji, Z. Zhong, X. Chen, et al., Bioorg. Med. Chem. Lett. 17(2007) 4275-4279. doi: 10.1016/j.bmcl.2007.05.020
22. [22]
  C.B. Vicentini, S. Guccione, L. Giurato, et al., J. Agric. Food Chem. 53(2005) 3848-3855. doi: 10.1021/jf0500029
23. [23]
  W.W. Lam, J.H. Kim, S.E. Sparks, et al., J. Agric. Food Chem. 41(1993) 1497-1502. doi: 10.1021/jf00033a027
24. [24]
  M. Nakamura, S. Noda, M. Kosugi, et al., Food Hyg. Saf. Sci. 51(2010) 213-219. doi: 10.3358/shokueishi.51.213
25. [25]
  L. Mao, H. Jiang, Q. Wang, et al., Crop Prot. 100(2017) 111-116. doi: 10.1016/j.cropro.2017.06.013
26. [26]
  S.F. Hwang, H.U. Ahmed, S.E. Strelkov, et al., Can. J. Plant Sci. 98(2018) 172-182.
27. [27]
  C.W. Huffman, E.M. Godar, K. Ohki, et al., J. Agric. Food Chem. 16(1968) 1041-1046. doi: 10.1021/jf60160a035
28. [28]
  F. Meyer, N. Ueberschaar, H.M. Dahse, et al., Bioorg. Med. Chem. Lett. 23(2013) 6043-6045. doi: 10.1016/j.bmcl.2013.09.033
29. [29]
  R.R. Soares, J.M.F. Silva, B.C. Carlos, et al., Bioorg. Med. Chem. Lett. 25(2015) 2308-2313. doi: 10.1016/j.bmcl.2015.04.014
30. [30]
  E.B. Park, K.J. Kim, H.R. Jeong, et al., Bioorg. Med. Chem. Lett. 26(2016) 5193-5197. doi: 10.1016/j.bmcl.2016.09.070
31. [31]
  L. Yang, P. Wang, J.F. Wu, et al., Bioorg. Med. Chem. 24(2016) 2125-2136. doi: 10.1016/j.bmc.2016.03.043
32. [32]
  S.A. Carvalho, E.F. Silva, M.V.N. Souza, et al., Bioorg. Med. Chem. Lett.18(2008) 538-541. doi: 10.1016/j.bmcl.2007.11.091
33. [33]
  X. Yu, P. Teng, Y.L. Zhang, et al., Fitoterapia 127(2018) 387-395. doi: 10.1016/j.fitote.2018.03.013
34. [34]
  W. Khalid, A. Badshah, A. Khan, et al., Chem. Cent. J. 11(2018) 1-16.
35. [35]
  G. Yu, L. Luo, S. Chen, et al., ChemistrySelect 3(2018) 10991-10995. doi: 10.1002/slct.201802434
36. [36]
  R.R. Pan, Z.Y. Feng, S.Y. Lu, et al., J. Anhui Agric. Sci. 4(1982) 55-60.
37. [37]
  X. Wang, Z.C. Dai, Y.F. Chen, et al., Eur. J. Med. Chem. 126(2017) 171-182. doi: 10.1016/j.ejmech.2016.10.006
38. [38]
  X. Wang, M. Wang, J. Yan, et al., ChemistrySelect 3(2018) 10663-10669. doi: 10.1002/slct.201801575
39. [39]
  X.X. Zhang, H. Jin, Y.J. Deng, et al., Chin. Chem. Lett. 28(2017) 1731-1736. doi: 10.1016/j.cclet.2017.04.021
40. [40]
  Y.T. Zheng, T.T. Zhang, P.Y. Wang, et al., Chin. Chem. Lett. 28(2017) 253-256. doi: 10.1016/j.cclet.2016.06.055
41. [41]
  W. Wang, X. Zhang, Y. Zhao, et al., Chin. Chem. Lett. 29(2018) 1872-1874. doi: 10.1016/j.cclet.2018.02.006
42. [42]
  H. Du, Z. Fan, L. Yang, et al., Mol. Divers. 22(2018) 1-10. doi: 10.1007/s11030-017-9782-3
43. [43]
  R.J. Wu, K.X. Zhou, H. Yang, et al., Eur. J. Med. Chem. 167(2019) 472-484. doi: 10.1016/j.ejmech.2019.02.002
44. [44]
  Z.J. Zhang, Y. Zeng, Z.Y. Jiang, et al., Pest Manage. Sci. 74(2018) 1736-1746.
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