Synthesis and herbicidal activity of 2-cyano-3-substituted-pyridinemethylaminoacrylates

Journal of Agricultural and Food Chemistry

Volumn 51, Issue 17, 2003, Pages 5030-5035

  Wang, Qingmin ^a   Sun, Huikai ^a   Cao, Huanyan ^a   Cheng, Muru ^a   Huang, Runqiu ^a  

^a NANKAI UNIVERSITY   (China)

Author keywords

2 Cyanoacrylates; Herbicidal activity; Inhibitors of PSII electron transport; Substituted pyridinemethaneamino

Indexed keywords

2 CYANO 3 METHYLTHIOPYRIDINEMETHANE AMINOACRYLATE; ACRYLIC ACID DERIVATIVE; HERBICIDE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHINA; CONCENTRATION (PARAMETERS); CROP PRODUCTION; ELECTRON TRANSPORT; HERBICIDAL ACTIVITY; INFRARED RADIATION; MASS SPECTROMETRY; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

CYANOACRYLATES; HERBICIDES; MOLECULAR STRUCTURE; PHOTOSYNTHETIC REACTION CENTER COMPLEX PROTEINS; PHOTOSYSTEM II PROTEIN COMPLEX; PYRIDINES; STRUCTURE-ACTIVITY RELATIONSHIP;

ZEA MAYS;

EID: 0042061123     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf034067s     Document Type: Article

References (19)

1. Banham, W. K.; Huppatz, J. L.; Phillips, J. N. N-Methylanilinocyanoacrylate photosystem II inhibitors. Structure-activity relationships. Z. Naturforsch. 1993, 48C, 136-139.
2. McFadden, H. G.; Phillips, J. N. Synthesis and use of radiolabeled cyanoacrylate probes of photosystem II herbicide binding site. Z. Naturforsch. 1990, 45C, 196-202.
3. McFadden, H. G.; Craig, D. C.; Huppatz, J. L.; Phillips, J. N. X-ray structure analysis of a cyanoacrylate inhibitor of photosystem II eletron transport. Z. Naturforsch. 1991, 46C, 93-98.
4. 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.
5. Phillips, J. N.; Huppatz, J. L. Cyanoacrylate inhibitors of the Hill reaction V. The effect of chirality on inhibitor binding. Z. Naturforsch. 1987, 42C, 684-689.
6. Phillips, J. N.; Banham, W. K. Hydrogen Bonding of Cyanoacrylates with the D1 peptide. Z. Naturforsch. 1993, 48C, 132-135.
7. Kluth, J.; Santel, H. J.; Schmidt, R. R. (Bayer AG). 3-Amino-2-cyanoacrylic acid ester herbicides. U.S. Patent 4,832,733, 1989; European Patent 0 241 826, 1987.
8. Huppatz, J. L. Quantifying the inhibitor-target site inteactions of Photosystem II herbicidal. Weed Sci. 1996, 44, 743-748.
9. Huppatz, J. L.; Phillips, J. N. Cyanoacrylate inhibitors of the Hill reaction IV. Binding Characteristics of the Hydrophobic Domain. Z. Naturforsch. 1987, 42C, 679-683.
10. Huppatz, J. L.; Phillips, J. N. Cyanoacrylate inhibitors of the Hill reactionIII. Stereochemical and electronic aspects of inhibitor binding. Z. Naturforsch. 1984, 39C, 617-622.
11. Zhao, Y.; Liu, X.; Huang, R.; Cheng, M.; Li, Z. The synthesis and biological activity assay of 2-cyano-3-substitutedamino-(methylthio)-3-(2-chloride-5-pyridinylmethyl) acrylate. Nongyao xue Xuebao 1999, 1, 93-95 (Ch).
12. Liu, X.; Huang, R.; Cheng, M.; Zhao, Y.; Li, Z. Synthesis and bioactivity of S,N-ketene acetal containing pyridine methylene. Chem. J. Chin. Univ. 1999, 20, 1404.
13. Wittig, G.; Schwarzenbach, K. Diazomethan. Ann. 1961, 650, 12.
14. 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.
15. Cheng, Z.; Gu, B.; Li, H.; Xia, G. The synthesis of acetamiprid. Pesticides (China) 1998, 37, 12.
16. Jones, R. G. Reactions of ortho esters with active methylene compounds. J. Am. Chem. Soc. 1952, 74, 4889.
17. Wang, X. J.; Huang, Z. T. Synthesis and spectral and structural characteristics of cyano substituted heterocyclic ketene aminals. Acta Chim. Sin. 1989, 47, 890.
18. Li, Y. Catalytic esterifications of carboxylic acids and alcohols by sodium bisulfate monohydrate. Synth. Commun. 1999, 29, 3901.
19. Cao, H.; Li, Z.; Sun, H.; Wang, Q.; Huang, R. Crystal structure of ethoxyethyl 3-(2-chloro-5-pyridylmethylamino)-2-cyano-4-methylpent-2-enoate. Chin. J. Struct. Chem. 2002, 21, 241-244.