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Chemical Research in Chinese Universities

, Volume 35, Issue 4, pp 609–615 | Cite as

Synthesis and Herbicidal Activity of 3-Acetyl-4-hydroxy-2,1-benzothiazine Derivatives

  • Kang LeiEmail author
  • Yang Liu
  • Shiben Wang
  • Bin Sun
  • Xuewen Hua
  • Xiaohua XuEmail author
Article
  • 28 Downloads

Abstract

In order to develop a novel herbicide containing the 2,1-benzothiazine motif, a series of 3-acetyl-4-hydroxy-2,1-benzothiazine derivatives was synthesized. All the target compounds were confirmed by 1H NMR, 13C NMR, and high-resolution mass spectrometry(HRMS). In addition, the crystal structure of compound T27 was determined by single crystal X-ray diffraction. The bioassay results showed that some of the 3-acetyl-4-hydroxy-2,1-benzothiazine derivatives(T13, T15, T22, and T24) showed good herbicidal activity at a dosage of 100 μg/mL. Among them, compounds T22 and T24 showed promising post-emergent herbicidal activities against Brassica campestris and Amaranthus retroflexus even at a dosage of 375 g/ha(1 ha=104 m2) in the greenhouse test. Studies on the structure-activity relationship demonstrated that the type of acetyl group played an important role in the herbicidal activity, and that the introduction of a phenoxyacetyl group at the 3-position of 2,1-benzothiazine was beneficial in improving the herbicidal activity. The present study also indicated that 3-phenoxyacetyl-4-hydroxy-2,1-benzothiazine could be a potential lead compound for further development of novel 2,1-benzothiazine-containing herbicides.

Keywords

3-Acetyl-4-hydroxy-2,1-benzothiazine Herbicidal activity Structure-activity relationship 

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Supplementary material

40242_2019_9029_MOESM1_ESM.pdf (1.4 mb)
Synthesis and Herbicidal Activity of 3-Acetyl-4-hydroxy-2,1-benzothiazine Derivatives

References

  1. [1]
    Lomabardino J. G., Wiseman E. H., McLamore W. M., J. Med. Chem., 1971, 14, 1171CrossRefGoogle Scholar
  2. [2]
    Türck D., Busch U., Heinzel G., Narjes H., Nehmiz G., Drug Invest., 1995, 9, 270CrossRefGoogle Scholar
  3. [3]
    Engelhardt G., Homma D., Schlegel K., Utzlnann R., Schnitzler C., Inflamm. Res., 1995, 44, 422Google Scholar
  4. [4]
    Myung P. S., Soon K. K., Bull. Korean Chem. Soc., 2000, 21, 1249Google Scholar
  5. [5]
    Caruso I., Montrone F., Boari L., Adv. Ther., 1994, 11, 132Google Scholar
  6. [6]
    Soler J. E., Derivatives of Oxazinobenzothiazine-6,6-dioxide, US 45634527, 1986 Google Scholar
  7. [7]
    Giuseppe M., Arnaldo F., Patrizia T., Derivatives of Pyridobenzothiazine with High Anti-microbial Activity, US 466878426, 1987 Google Scholar
  8. [8]
    Ikeda T., Kakegawa H., Miyataka H., Matsumoto H., Satoht T., Bio. Med. Chem. Lett., 1992, 2, 709CrossRefGoogle Scholar
  9. [9]
    Krapcho J., Turk C. F., 1-Substituted-4-phenyl-4H-[1,2,4]triazolo-[3,4-c][1,4]benzothiazines or Benzoxazines, US 3929783, 1975 Google Scholar
  10. [10]
    Constantine J. W., Nature, 1967, 214, 1084CrossRefGoogle Scholar
  11. [11]
    Barreca M. L., Manfroni G., Leyssen P., Winquist J., Kaushik-Basu N., Paeshuyse J., Krishnan R., Iraci N., Sabatini S., Tabarrini O., Basu A., Danielson U. H., Neyts J., Cecchetti V., J. Med. Chem., 2013, 56, 2270CrossRefGoogle Scholar
  12. [12]
    Aslam S., Ahmad M., Athar M. M., Ashfaq U. A., Gardiner J. M., Montero C., Detorio M., Parvez M., Schinazi R. F., Med. Chem. Res., 2014, 23, 2930CrossRefGoogle Scholar
  13. [13]
    Lei K., Hua X. W., Tao Y. Y., Liu Y., Liu N., Ma Y., Li Y. H., Xu X. H., Kong C. H., Bioorg. Med. Chem., 2016, 24, 92CrossRefGoogle Scholar
  14. [14]
    Yang X. F., Lei K., Kong C. H., Xu X. H., Pestic. Biochem. Phys., 2017, 143, 224CrossRefGoogle Scholar
  15. [15]
    Coppo F. T., Fawzi M. M., J. Heterocycl. Chem., 1998, 35, 983CrossRefGoogle Scholar
  16. [16]
    Volovenko Y., Volovnenko T., Popov K., J. Heterocycl. Chem., 2007, 44, 1413CrossRefGoogle Scholar
  17. [17]
    Muhammad S., Muhammad Z. U. R., Islam U. K., Muhammad N. A., Siraj A. K., J. Chil. Chem. Soc., 2011, 56, 527CrossRefGoogle Scholar
  18. [18]
    Ogawa H., Yamada I., Arai K., Hirase K., Moriyasu K., Schneider C., Pest Manag. Sci., 2001, 57, 33CrossRefGoogle Scholar
  19. [19]
    Wang B. L., Duggleby R. G., Li Z. M., Wang J. G., Li Y. H., Wang S. H., Pest Manag. Sci., 2005, 61, 407CrossRefGoogle Scholar
  20. [20]
    Zhang M., Xu X. H., Cui Y., Xie L. G., Kong C. H., Pest Manag. Sci., 2012, 68, 1512CrossRefGoogle Scholar

Copyright information

© Jilin University, The Editorial Department of Chemical Research in Chinese Universities and Springer-Verlag GmbH 2019

Authors and Affiliations

  1. 1.School of PharmacyLiaocheng UniversityLiaochengP. R. China
  2. 2.State Key Laboratory of Elemento-Organic ChemistryNankai UniversityTianjinP. R. China
  3. 3.College of AgricultureLiaocheng UniversityLiaochengP. R. China

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