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

doi:10.1007/s40242-019-9029-1

Chemical Research in Chinese Universities ›› 2019, Vol. 35 ›› Issue (4): 609-615.doi: 10.1007/s40242-019-9029-1

• Articles • Previous Articles Next Articles

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

LEI Kang^1,2, LIU Yang^1,2, WANG Shiben¹, SUN Bin¹, HUA Xuewen³, XU Xiaohua²

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

Received:2019-01-29 Revised:2019-03-25 Online:2019-08-01 Published:2019-08-01
Contact: LEI Kang, XU Xiaohua E-mail:leikang@lcu.edu.cn;xiaohuaxu@nankai.edu.cn
Supported by:
Supported by the National Natural Science Foundation of China(No.31701827) and the Natural Science Foundation of Shandong Province, China(Nos.ZR2017BH037, ZR2017BC053).

Abstract

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.

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

LEI Kang, LIU Yang, WANG Shiben, SUN Bin, HUA Xuewen, XU Xiaohua. Synthesis and Herbicidal Activity of 3-Acetyl-4-hydroxy-2,1-benzothiazine Derivatives[J]. Chemical Research in Chinese Universities, 2019, 35(4): 609-615.

References 20

[1]	Lomabardino J. G., Wiseman E. H., McLamore W. M., J. Med. Chem., 1971, 14, 1171
[2]	Türck D., Busch U., Heinzel G., Narjes H., Nehmiz G., Drug Invest., 1995, 9, 270
[3]	Engelhardt G., Homma D., Schlegel K., Utzlnann R., Schnitzler C., Inflamm. Res., 1995, 44, 422
[4]	Myung P. S., Soon K. K., Bull. Korean Chem. Soc., 2000, 21, 1249
[5]	Caruso I., Montrone F., Boari L., Adv. Ther., 1994, 11, 132
[6]	Soler J. E., Derivatives of Oxazinobenzothiazine-6,6-dioxide, US 45634527, 1986
[7]	Giuseppe M., Arnaldo F., Patrizia T., Derivatives of Pyridobenzothia-zine with High Anti-microbial Activity, US 466878426, 1987
[8]	Ikeda T., Kakegawa H., Miyataka H., Matsumoto H., Satoht T., Bio. Med. Chem. Lett., 1992, 2, 709
[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
[10]	Constantine J. W., Nature, 1967, 214, 1084
[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, 2270
[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, 2930
[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, 92
[14]	Yang X. F., Lei K., Kong C. H., Xu X. H., Pestic. Biochem. Phys., 2017, 143, 224
[15]	Coppo F. T., Fawzi M. M., J. Heterocycl. Chem., 1998, 35, 983
[16]	Volovenko Y., Volovnenko T., Popov K., J. Heterocycl. Chem., 2007, 44, 1413
[17]	Muhammad S., Muhammad Z. U. R., Islam U. K., Muhammad N. A., Siraj A. K., J. Chil. Chem. Soc., 2011, 56, 527
[18]	Ogawa H., Yamada I., Arai K., Hirase K., Moriyasu K., Schneider C., Pest Manag. Sci., 2001, 57, 33
[19]	Wang B. L., Duggleby R. G., Li Z. M., Wang J. G., Li Y. H., Wang S. H., Pest Manag. Sci., 2005, 61, 407
[20]	Zhang M., Xu X. H., Cui Y., Xie L. G., Kong C. H., Pest Manag. Sci., 2012

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

Knowledge

Abstract

Cite this article

share this article

References 20

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	ZHANG Shujing, XIAO Jiapeng, CHEN Xinyi, LI Yu. Insulation and Flame Retardancy Improvement of PBDEs Using 3D-QSAR Model Combined with a Fuzzy Membership Function Method [J]. Chemical Research in Chinese Universities, 2021, 37(3): 729-738.
[2]	CAO Yangyang, CAI Zengfei, ZHANG Wenliang, DU Xiaohua. Synthesis and Herbicidal Activity of Novel β-Methoxyacrylate Derivatives Containing a Substituted Phenylpyridine Moiety [J]. Chemical Research in Chinese Universities, 2019, 35(6): 1008-1011.
[3]	ZHANG Xiaoyi, NIU Wenling, TANG Tang, HOU Chengfei, GUO Yajie, KONG Ren. A Strategy to Find Novel Candidate DKAs Inhibitors Using Modified QSAR Model with Favorable Druggability Properties [J]. Chemical Research in Chinese Universities, 2019, 35(6): 1111-1118.
[4]	LIU Sicheng, SUN Shijun. Combined QSAR/QSPR, Molecular Docking, and Molecular Dynamics Study of Environmentally Friendly PBDEs with Improved Insulating Properties [J]. Chemical Research in Chinese Universities, 2019, 35(3): 478-484.
[5]	CHEN Chen, WANG Ping, ZOU Liwei, YANG Ling, FAN Yiming, HU Wenzhong, GE Guangbo. Synthesis and Biological Evaluation of Hydroxylcoumarin Derivatives as Antioxidant Agents [J]. Chemical Research in Chinese Universities, 2017, 33(2): 194-199.
[6]	CAI Wenqing, LIU Wei, XIE Yafei, WU Jingwei, LIU Yuqiang, LIU Changying, XU Weiren, TANG Lida, WANG Jianwu, ZHAO Guilong. Design, Synthesis and Biological Activity of Tetrazole-bearing Uric Acid Transporter 1 Inhibitors [J]. Chemical Research in Chinese Universities, 2017, 33(1): 49-60.
[7]	LIN Ding, XIAO Mengwu, YANG Zihui, LI Beibei, HU Aixi, YE Jiao. Synthesis and Herbicidal Activity of N-(2,2-Dimethyl-7-alkoxy-2,3-dihydrobenzofuran-5-yl)-2-(4-arylxoyphenoxy)propionamides [J]. Chemical Research in Chinese Universities, 2017, 33(1): 74-79.
[8]	LI Hongshuang, WANG Xinran, DUAN Guiyun, XIA Chengcai, XIAO Yuliang, LI Furong, GE Yanqing, YOU Guirong, HAN Junfen, FU Xiaopan, TAN Shanhui, WANG Rongwei. Synthesis, Antitumor Activity and Preliminary Structure-activity Relationship of 2-Aminothiazole Derivatives [J]. Chemical Research in Chinese Universities, 2016, 32(6): 929-937.
[9]	XUE Hansong, LIU Aiping, LIU Weidong, LI Jianming, REN Yeguo, HUANG Lu, HE Lian, OU Xiaoming, YE Jiao, HUANG Mingzhi. Syntheses and Fungicidal Activities of Thiazole-5-carboxanilides Bearing Thioether Group [J]. Chemical Research in Chinese Universities, 2016, 32(5): 781-785.
[10]	ZHANG Dongkai, HUA Xuewen, LIU Ming, WU Changchun, WEI Wei, LIU Yang, CHEN Minggui, ZHOU Sha, LI Yonghong, LI Zhengming. Design, Synthesis and Herbicidal Activity of Novel Sulfonylureas Containing Triazole and Oxadiazole Moieties [J]. Chemical Research in Chinese Universities, 2016, 32(4): 607-614.
[11]	HUA Xuewen, ZHOU Sha, CHEN Minggui, ZHANG Dongkai, LIU Ming, LIU Jingbo, WU Changchun, LIU Yang, LI Yonghong, LI Zhengming. Design, Synthesis and Herbicidal Activity of Novel Sulfonylureas Containing Tetrahydrophthalimide Substructure [J]. Chemical Research in Chinese Universities, 2016, 32(3): 396-401.
[12]	XU Zheng, CHEN Ying, QIU Youli, GU Wenwen, LI Yu. Prediction of Stability for Polychlorinated Biphenyls in Transformer Insulation Oil Through Three-dimensional Quantitative Structure-activity Relationship Pharmacophore Model and Full Factor Experimental Design [J]. Chemical Research in Chinese Universities, 2016, 32(3): 348-356.
[13]	LIU Qixing, HUANG Mingzhi, LIU Aiping, HU Aixi, LEI Manxiang, REN Yeguo, HUANG Lu. Synthesis and Herbicidal Activity of Novel N-Allyloxy/Propargyloxy Aryloxyphenoxy Propionamide Derivatives [J]. Chemical Research in Chinese Universities, 2016, 32(2): 188-194.
[14]	LI Yu, JIANG Long. Solvent Effect on Characteristic Vibration of IR Spectrum of 4,4'-Dibromodiphenyl Ether [J]. Chemical Research in Chinese Universities, 2014, 30(6): 997-1004.
[15]	ZHANG Shuo, WANG Yuli, LIU Wei, XIE Yafei, LIU Yuqiang, XU Weiren, TANG Lida, WANG Jianwu, ZHAO Guilong. 3-Oxodapagliflozin as a Potent and Highly Selective SGLT2 Inhibitor for the Treatment of Type 2 Diabetes [J]. Chemical Research in Chinese Universities, 2014, 30(5): 785-793.