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


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.


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


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


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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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