Synthesis and Herbicidal Activity of 3-Acetyl-4-hydroxy-2,1-benzothiazine Derivatives |
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Authors: | LEI Kang LIU Yang WANG Shiben SUN Bin HUA Xuewen XU Xiaohua |
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Affiliation: | 1. School of Pharmacy, Liaocheng University, Liaocheng 252000, P. R. China;2. State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. China;3. College of Agriculture, Liaocheng University, Liaocheng 252000, P. R. China |
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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. |
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Keywords: | 3-Acetyl-4-hydroxy-2 1-benzothiazine Herbicidal activity Structure-activity relationship |
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