Synthesis, herbicidal activities, and 3D-QSAR of 2-cyanoacrylates containing aromatic methylamine moieties

Journal of Agricultural and Food Chemistry

Volumn 56, Issue 1, 2008, Pages 204-212

  Liu, Yu Xiu ^a,b   Wei, Deng Guo ^b   Zhu, Ye Rong ^a   Liu, Shao Hua ^a   Zhang, Yong Lin ^a   Zhao, Qi Qi ^a   Cai, Bao Li ^a   Li, Yong Hong ^a   Song, Hai Bin ^a   Liu, Ying ^b   Wang, Yong ^a   Huang, Run Qiu ^a   Wang, Qing Min ^a  

^a NANKAI UNIVERSITY   (China)

^b PEKING UNIVERSITY   (China)

Author keywords

2 cyanoacrylates; Aromatic rings; CoMFA; Herbicides; Photosynthetic electron transport inhibitors

Indexed keywords

CYANOACRYLATE DERIVATIVE; HERBICIDE; METHYLAMINE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; QUANTITATIVE STRUCTURE ACTIVITY RELATION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; CYANOACRYLATES; HERBICIDES; MAGNETIC RESONANCE SPECTROSCOPY; METHYLAMINES; MODELS, MOLECULAR; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 38549157971     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf072851x     Document Type: Article

References (17)

1. Phillips, J. N.; Huppatz, J. L. Cyanoacrylate inhibitors of the Hill reaction III. Stereochemical and electronic aspects of inhibitor binding. Z. Naturforsch. 1984, 39C, 617-622.
2. Huppatz, J. L.; Mcfadden, H. G.; Huber, M.-L.; McCaffery, L. F. Cyanoacrylate inhibitors of photosynthetic electron transport. Structural requirements for inhibitor potency and herbicidal activity. In Synthesis and Chemistry of Agrochemicals III; Baker, D. R., Fenyes, J. G., Steffens, J. J., Eds.; Maple Press: New York, 1992; pp 186-199.
3. Mackay, S. P.; O'Malley, P. J. Molecular modelling of the interaction of cyanoacrylate inhibitors with photosystem II. Part I. Z. Naturforsch. 1993, 48C, 773-781.
4. Huppatz, J. L. Quantifying the inhibitor-target site interactions of photosystem II herbicides. Weed Sci. 1996, 44, 743-748.
5. Wang, Q.; Sun, H.; Cao, H.; Cheng, M.; Huang, R. Synthesis and herbicidal activity of 2-cyano-3-substituted-pyridinemethylaminoacrylates. J. Agric. Food Chem. 2003, 51, 5030-5035.
6. Sun, H.; Wang, Q.; Huang, R.; Li, H.; Li, Y. Synthesis and biological activity of novel cyanoacrylates containing ferrocenyl moiety. J. Organomet. Chem. 2002, 655, 182.
7. Wang, Q.; Li, H.; Cao, H.; Li, Y.; Huang, R. Synthesis and herbicidal activity of 2-cyano-3-(2-chlorothiazol-5-yl)methylaminoacrylates. J. Agric. Food Chem. 2004, 52, 1918-1922.
8. Liu, Y.; Zhao, Q.; Wang, Q.; Li, H.; Huang, R.; Li, Y. Synthesis and herbicidal activity of 2-cyano-3-(2-fluoro-5-pyridyl)methylaminoacrylates. J. Fluorine Chem. 2005, 126, 345-348.
9. Liu, Y.; Li, H.; Zhao, Q.; Wang, Q.; Huang, R. Synthesis and herbicidal activity of ethoxyethyl 2-cyano-3-(substituted)pyridinemethylamino-3- (substituted)acrylates. Chin. J. Org. Chem. 2006, 26 (9), 1232-1238.
10. Liu, Y.; Cai, B.; Li, Y.; Song, H.; Huang, R.; Wang, Q. Synthesis, crystal structure, and biological activities of 2-cyanoacrylates containing furan or tetrahydrofuran moieties. J. Agric. Food Chem. 2007, 55, 3011-3017.
11. Yang, G. F.; Huang, X. Q. Development of quantitative structure-activity relationships and its application in rational drug design. Curr. Pharm. Design 2006, 12 (35), 4601-4611.
12. Windscheif, P. M.; Voegtle, F. Substituted dipyridylethenes and ethynes and key pyridine building blocks. Synthesis 1994, 1, 87-92.
13. Kurkjy, R. P.; Brown, E. V. The preparation of thiazole grignard reagents and thiazolyllithium compounds. J. Am. Chem. Soc. 1952, 74, 6260-6262.
14. Overend, W. G.; Wiggins, L. F. The conversion of sucrose into pyridazine derivatives. Part I. 3-Sulphanilamido-6-methylpyridazine. J. Chem. Soc. 1947, 1, 239-243.
15. Schmidt-Nickels, W.; Johnson, T. B. Researches on pyrimidines. CXVIII. Molecular rearrangements in the thymine series. J. Am. Chem. Soc. 1930, 52, 4511-4516.
16. Bedel, S.; Ulrich, G.; Picard, C. Alternative approach to the free radical bromination of oligopyridine benzylic-methyl group. Tetrahedron Lett. 2002, 43 (9), 1697-1700.
17. Holt, A. S.; French, C. S. Oxygen production by illuminated chloroplasts suspended in solution of oxidants. Arch. Biochem. 1948, 19, 368-378.