Synthesis and herbicidal activity of novel 3-aminocarbonyl-2- oxazolidinethione derivatives containing a substituted pyridine ring

Journal of Agricultural and Food Chemistry

Volumn 54, Issue 1, 2006, Pages 125-129

  Li, Gangyue ^a   Qian, Xuhong ^a,b   Cui, Jingnan ^a   Huang, Qingchun ^b   Zhang, Rong ^a   Guan, Huai ^a  

^a DALIAN UNIVERSITY OF TECHNOLOGY   (China)

^b EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

2 Oxazolidinethiones; Herbicidal activity; Pyridine ring

Indexed keywords

HERBICIDE; OXAZOLE DERIVATIVE; PYRIDINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

HERBICIDES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; OXAZOLES; PYRIDINES; STRUCTURE-ACTIVITY RELATIONSHIP;

BRASSICA RAPA; BRASSICA RAPA SUBSP. PEKINENSIS; CUCUMIS SATIVUS; DIGITARIA SANGUINALIS; ECHINOCHLOA; ECHINOCHLOA CRUS-GALLI; ECLIPTA; SORGHUM BICOLOR;

EID: 31044453810     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf051928j     Document Type: Article

References (15)

1. Böger, P.; Wakabayashi, K.; Hirai, K. Herbicide Classes in Development. Mode of Action, Targets, Genetic Engineering, Chemistry; Springer-Verlag: Berlin, Germany, 2002; ISBN 0540431470, 364 pp.
2. Heap, I. International Survey of Herbicide Resistant Weeds; http://www.weedscience.org (accessed Sept 21, 2005).
3. Liu, M. C.; Lin, T. S.; Cory, J. G.; Cory, A. H.; Sartorelli, A. C. Synthesis and biological activity of 3- and 5-amino derivatives of pyridine-2-carboxaldehyde thiosemicarbazone. J. Med. Chem. 1996, 39, 2586-2593.
4. Finkelstein, B. L.; Martz, M. A.; Strock, C. J. Synthesis and insecticidal activity of novel pyridine methanesulfonates. Pestic. Sci. 1997, 50, 319-323.
5. Wang, Q. M.; Sun, H. K.; Cao, H. Y.; Cheng, M. R.; Huang, R. Q. Synthesis and herbicidal activity of 2-cyano-3-substituted-pyridinemethylaminoacrylates. J. Agric. Food Chem. 2003, 51, 5030-5035.
6. Jo, Y. W.; Im, W. B.; Rhee, J. K.; Shim, M. J.; Kim, W. B.; Choi, E. C. Synthesis and antibacterial activity of oxazolidinones containing pyridine substituted with heteroaromatic ring. Bioorg. Med. Chem. 2004, 12, 5909-5915.
7. Ettlinger, M. G. Synthesis of the natural antithyroid factor 1-5-vinyl-2-thiooxazolidone. J. Am. Chem. Soc. 1950, 72, 4792-4796.
8. Eichel, H. J.; Meyer, R. J.; Buzzi, P. F. Substituted 2-oxazolidinethiones. J. Med. Chem. 1967, 10, 942-944.
9. Youngdale, G. A.; Duncan, G. W.; Emmert, D. E.; Lednicer, D. Synthesis and antifertility activity of 5-(phenoxymeththyl)-2-oxazolidinethione. J. Med. Chem. 1966, 9, 155-157.
10. Lednicer, D.; Emmert, D. E. Synthesis and antifertility activity of 4- and 5-(ω-arylalkyl)oxazolidinethiones. J. Med. Chem. 1968, 11, 1258-1262.
11. Johnson, G. A.; Kim, E. G.; Boukma, S. J.; Lednicer, D.; Youngdale, G. A. Inhibition of dopamine β-hydroxylase by 5-phenoxymethyl-2- oxazolidinethiones. J. Med. Chem. 1972, 15, 327-329.
12. Seneci, P.; Caspani, M.; Ripamonti, F.; Ciabatti, R. Synthesis and antimicrobial activity of oxazolidin-2-ones and related heterocycles. J. Chem. Soc., Perkin Trans. 1 1994, 16, 2345-2351.
13. Sattigeri, V. J.; Soni, A.; Singhal, S.; Khan, S.; Pandya, M.; Bhateja, P.; Mathur, T.; Rattan, A.; Khanna, J. M.; Mehta, A. Synthesis and antimicrobial activity of novel thiazolidinones. ARKIVOC (Gainesville, FL, U.S.) 2005, ii, 46-59.
14. Gandhi, N.; Srivastava, B. K.; Lohray, V. B.; Lohray, B. B. Oxazolidine-2-thiones: a molecular modeling study. Tetrahedron Lett. 2004, 45, 6269-6272.
15. Delaunay, D.; Toupet, L.; Corre, M. L. Reactivity of β-amino alcohols with carbon disulfide. Study on the synthesis of 2-oxazolidinethiones and 2-thiazolidinethiones. J. Org. Chem. 1995, 60, 6604-6607.