Design, Synthesis and Herbicidal Activities of Tetrahydroisoindoline-1,3-dione Derivatives Containing Alkoxycarbonyl Substituted 2-Benzoxazolinone
Hao Zhang
Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China
Search for more papers by this authorKechang Liu
Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China
Search for more papers by this authorRuiquan Liu
Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China
Search for more papers by this authorQibo Li
Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China
Search for more papers by this authorYongqiang Li
State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China
Search for more papers by this authorCorresponding Author
Qingmin Wang
State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China
Qingmin Wang, State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China
Shangzhong Liu, Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China, Tel.: 0086-010-62731070; Fax: 0086-010-62731070
Search for more papers by this authorCorresponding Author
Shangzhong Liu
Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China
Qingmin Wang, State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China
Shangzhong Liu, Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China, Tel.: 0086-010-62731070; Fax: 0086-010-62731070
Search for more papers by this authorHao Zhang
Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China
Search for more papers by this authorKechang Liu
Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China
Search for more papers by this authorRuiquan Liu
Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China
Search for more papers by this authorQibo Li
Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China
Search for more papers by this authorYongqiang Li
State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China
Search for more papers by this authorCorresponding Author
Qingmin Wang
State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China
Qingmin Wang, State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China
Shangzhong Liu, Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China, Tel.: 0086-010-62731070; Fax: 0086-010-62731070
Search for more papers by this authorCorresponding Author
Shangzhong Liu
Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China
Qingmin Wang, State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China
Shangzhong Liu, Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China, Tel.: 0086-010-62731070; Fax: 0086-010-62731070
Search for more papers by this authorAbstract
Several different alkoxycarbonyl-substituted 2-benzoxazolinone moieties have been incorporated into a tetrahydroisoindoline-1,3-dione scaffold to provide 25 compounds (1a–1u and 2a–2d). The structures of these compounds were confirmed by 1H and 13C NMR, HRMS and X-ray single-crystal diffraction. Some of these compounds (1g, 1h, 1j, 1k) exhibited excellent herbicidal activities against Abutilon theophrasti, Amaranthus retroflexus and Echinochloa crus-galli at a rate of 375 g AI·ha−1. Among them, compounds 1h and 1j displayed the best post-emergence herbicidal effect against Abutilon theophrasti with ED50 values of 1.8 and 5.3 g AI·ha−1, respectively, which are superior to that of the commercial acifluorfen (44.3 g AI·ha−1). Field trials demonstrated that compound 1h exhibited similar herbicidal activity to a high concentration atrazine, and found to be safer for maize than atrazine. The results of this study therefore show that compound 1h could potentially be used as a post-emergence herbicide for maize fields.
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REFERENCES
- 1 Gianessi, L. P.. Pest Manag. Sci., 2013, 69, 1099.
- 2 Heap, I.. Pest Manag. Sci., 2014, 70, 1306.
- 3 Hao, G. F.; Tan, Y.; Xu, W. F.; Cao, R. J.; Xi, Z.; Yang, G. F.. J. Agric. Food Chem., 2014, 62, 7209.
- 4 He, T. T.; Yang, J. C.; Liu, Y. P.. Agrochemicals, 2011, 50, 440 (in Chinese).
- 5 Nagano, E.; Haga, T.; Sato, R.; Morita, K., EP 170191 Chem. Abstr., 1986, 105, 56350.
- 6 Cahoon, C. W.; York, A. C.; Jordan, D. L.; Everman, W. J.; Seagroves, R. W.. Weed Technol., 2014, 28, 58.
- 7 Ashigh, J.; Hall, J. C.. J. Agric. Food Chem., 2010, 58, 7335.
- 8 Zhang, H.; Li, Q. B.; Liu, K. C.; Liu, R. Q.; Li, Q. Y.; Wang, Q. M.; Liu, S. Z.. Chin. J. Org. Chem., 2015, 35, 159 (in Chinese).
- 9 Modern Crop Protection Compounds, 2nd ed., Eds.: W. Kräomer; U. Schirmer; P. Jeschke; M. Witschel, Wiley-VCH, Weinheim, Germany, 2012, p. 163.
- 10a Yang, S. G.; Hao, G. F.; Dayan, F. E.; Tranel, P. J.; Yang, G. F.. Chin. J. Chem., 2013, 31, 1153.
- 10b Dong, X. L.; Zhou, Y. H.; Xu, S. S.; Qu, J. P.. Chin. J. Org. Chem., 2011, 31, 1020 (in Chinese).
- 11a Li, H. B.; Zhu, Y. Q.; Song, X. W.; Hu, F. Z.; Liu, B.; Li, Y. H.; Niu, Z. X.; Liu, P.; Wang, Z. H.; Song, H. B.; Zou, X. M.; Yang, H. Z. J.. Agric. Food Chem., 2008, 56, 9535.
- 11b Lyga, J. W.; Chang, J. H.; Theodoridis, G.; Baum, J. S.. Pestic. Sci., 1999, 55, 281.
- 12 Crawford, S. D.; Maravetz, L. L.; Theodoridis, G., US 5661108 Chem. Abstr., 1997, 127, 248123.
- 13a Jiang, L. L.; Zuo, Y.; Wang, Z. F.; Tan, Y.; Wu, Q. Y.; Xi, Z.; Yang, G. F.. J. Agric. Food Chem., 2011, 59, 6172.
- 13b Wu, Q. Y.; Jiang, L. L.; Yang, S. G.; Zuo, Y.; Wang, Z. F.; Xi, Z.; Yang, G. F.. New J. Chem., 2014, 38, 4510.
- 14 Yoshida, R.; Sakaki, M.; Sato, R.; Haga, T.; Nagano, E.; Oshio, H.; Kamoshita, H., In Proceedings of the Brighton Crop Protection Conference-Weeds, BCPC, Surrey, United Kingdom, 1991, p. 69.
- 15 Singh, H. P.; Batish, D. R.; Kaur, S.; Setia, N.; Kohli, R. K.. Ann. Appl. Biol., 2005, 147, 267.
- 16a Chum, M.; Batish, D. R.; Singh, H. P.; Kohli, R. K.. J. Environ. Biol., 2012, 33, 21.
- 16b Kato-Noguchi, H.; Macías, F. A.. J. Plant Physiol., 2005, 162, 1304.
- 16c Fernández-Aparicio, M.; Cimmino, A.; Evidente, A.; Rubiales, D.. J. Agric. Food Chem., 2013, 61, 9797.
- 17 Burgos, N. R.; Talbert, R. E.. Weed Sci., 2000, 48, 302.
- 18 Modern Crop Protection Compounds, 2nd ed., Ed.: W. Kräomer, Wiley-VCH, Weinheim, Germany, 2012, p. 1108.
- 19 Macías, F. A.; Marín, D.; Oliveros-Bastidas, A.; Molinillo, J. M. G.. J. Agric. Food Chem., 2006, 54, 9357.
- 20 Wang, Q. M.; Sun, H. K.; Cao, H. Y.; Cheng, M. R.; Huang, R. Q.. J. Agric. Food Chem., 2003, 51, 5030.
- 21 Abel, M. D.; Cameron, A. D.; Ha, C. M.; Koski, C. A.; Luu, H. T.; Micetich, R. G.; Nguyen, D. Q.; Tempest, M. L.; Daneshtalab, M.. Antiviral Chem. Chemother., 1995, 6, 245.
- 22 Supplementary material CCDC-1043344 contains the supplementary crystallographic data for compound 1h. Copies of the data can be obtained, free of charge, on application to Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB 21EZ, UK, Fax: +44-1223-336033. Email: [email protected].
