Quantifying the inhibitor-target site interactions of photosystem II herbicides

Weed Science

Volumn 44, Issue 3, 1996, Pages 743-748

  Huppatz, John L ^a  

^a CSIRO   (Australia)

Author keywords

cyanoacrylate inhibitors; molecular modelling; QSAR

Indexed keywords

BACTERIA (MICROORGANISMS); EMBRYOPHYTA; PHOTOBACTERIA;

EID: 0029823693     PISSN: 00431745     EISSN: None     Source Type: Journal    
DOI: 10.1017/s0043174500094625     Document Type: Conference Paper

References (43)

1. Bowyer, J., M. Hilton, J. Whitelegge, P. Jewess, P. Camilleri, A. Crofts, and H. Robinson. 1990. Molecular modelling studies on the binding of phenylurea inhibitors to the D1 protein of Photosystem II. Z. Naturforsch. 45c:379-387.
2. Brown, B. T., J. N. Phillips, and B. M. Rattigan. 1981. 3-Alkoxyuracil derivatives. 2. Hill inhibitory activity. J. Agric. Food Chem. 29:719-722.
3. Camilleri, P., D. P. Astles, M. W. Kerr, and J. E. Spencer. 1990. Aminopyrazolones: novel Photosystem II inhibitors. J. Agric. Food Chem. 38:1601-1603.
4. Camilleri, P., M. D. Barker, M. W. Kerr, M. K. Whitehouse, J. R. Bowyer, and R. J. Lewis. 1989. Structure-activity studies on the inhibition of Photosystem II electron transport by phenylbiurets. J. Agric. Food Chem. 37:1509-1513.
5. Camilleri, P., J. R. Bowyer, T. Gilkerson, B. Odell, and R. C. Weaver. 1987. Structure-activity relationships in the Hill inhibitory activity of substituted phenylureas. J. Agric. Food Chem. 35:479-483.
6. Deisenhofer, J., O. Epp, K. Miki, R. Huber, and H. Michel. 1984. X-ray structure analysis of a membrane protein complex. J. Mol. Biol. 180:385-398.
7. Deisenhofer, J., O. Epp, K. Miki, R. Huber, and H. Michel. 1985. Structure of the protein subunits in the photosynthetic reaction center of Rhodopseudomonas viridis at 3Å resolution. Nature 318:618-624.
8. Draber, W., K. Dickore, K. H. Buchel, A. Trebst, and E. Pistorius. 1968. Struktur-activität-korrelation bei 1,2,4-triazinonen, einer neuen gruppe von photosynthesehemmem. Naturwissenschaften 55:446.
9. Fedtke, C. 1982. Biochemistry and Physiology of Herbicide Action. Springer Verlag, Berlin. Pages 18-60.
10. Gardner, G. 1981. Azidoatrazine: photoaffinity label for the site of triazine herbicide action in chloroplasts. Science 211:937-940.
11. Gardner, G. and J. R. Sanborn. 1987. The role of chirality in the activity of Photosystem II herbicides. Z. Naturforsch 42c:663-669.
12. Hansch, C. and E. Deutsch. 1966. The structure-activity relationship in amides inhibiting photosynthesis. Biochim. Biophys Acta. 112:381-391.
13. Hansch, C. and T. Fujita. 1964. ρ-σ-π Analysis. A method for the correlation of biological activity and chemical structure. J. Amer Chem. Soc. 86:1616-1626.
14. Hirschberg, J., A. Bleeker, D. J. Kyle, L. McIntosh, and C. J. Arntzen. 1984. The molecular basis of triazine-herbicide resistance in higher-plant chloroplasts. Z. Naturforsch 39c:412-420.
15. Hirschberg, J. and L. McIntosh. 1983. Molecular basis of herbicide resistance in Amaranthus hybridus. Science 222:1346-1348.
16. Huppatz, J. L., H. G. McFadden, M-L. Huber, and L. F. McCaffery. 1992. Cyanoacrylate inhibitors of photosynthetic electron transport. Structural requirements for inhibitor potency and herbicidal activity. Pages 186-199 in D. R. Baker, J. G. Fenyes, and J. J. Steffens, eds. Synthesis and Chemistry of Agrochemicals III. ACS Symposium, Series 504. Amer. Chem. Soc., Washington, DC.
17. Huppatz, J. L. and H. G. McFadden. 1993. Understanding the topography of the Photosystem II herbicide binding niche: does QSAR help? Z. Naturforsch. 48c:140-145.
18. Huppatz, J. L., H. G. McFadden, and L. F. McCaffery. 1990. Cyanoacrylate inhibitors as probes for the nature of the Photosystem II herbicide binding site. Z. Naturforsch. 45:336-342.
19. Huppatz, J. L., J. N. Phillips, and B. M. Rattigan. 1981. Cyanoacrylates. Herbicidal and photosynthetic inhibitory activity. Agric. Biol. Chem. 45:2769-2773.
20. Huppatz, J. L. and J. N. Phillips. 1987. Stereospecific inhibitor probes of the PSII herbicide binding site. Z. Naturforsch. 42c:674-678.
21. Huppatz, J. L. and J. N. Phillips. 1987. Cyanoacrylate inhibitors of the Hill reaction IV. Binding characteristics of the hydrophobic domain. Z. Naturforsch. 42c:679-683.
22. Huppatz, J. L. and J. N. Phillips. 1987. Cyanoacrylate inhibitors of the Hill reaction. V. The effect of chirality on inhibitor binding. Z. Naturforsch. 42c:684-689.
23. Kakkis, E., V. C. Palmire, Jr., C. D. Strong, W. Bertsch, C. Hansch, and U. Schirmer. 1984. Quantitative structure-activity relationships in the inhibition of Photosystem II in chloroplasts by phenylureas. J. Agric. Food Chem. 32:133-144.
24. Macdowall, F. D. 1949. The effects of some inhibitors of photosynthesis upon the photochemical reduction of a dye by isolated chloroplasts. Plant Physiol. 24:462-480.
25. B-binding site of Photosystem II. Z. Naturforsch 48c:191-198.
26. Mackay, S. P. and P. J. O'Malley. 1993. Molecular modelling of the interactions between optically active triazine herbicides and Photosystem II. Z. Naturforsch. 48c:474-481.
27. Mackay, S. P. and P. J. O'Malley. 1993. Molecular modelling of the interaction of cyanoacrylate inhibitors with Photosystem II. Part 1. The effect of hydrophobicity of inhibitor binding. Z. Naturforsch. 48c:773-781.
28. Mackay, S. P. and P. J. O'Malley. 1993. Molecular modelling of the interaction of cyanoacrylate inhibitors with Photosystem II. Part 2. The effect of stereochemistry of inhibitor binding. Z. Naturforsch. 48c:782-787.
29. McFadden, H. G., D. C. Craig, J. L. Huppatz, and J. N. Phillips. 1991. X-ray structure analysis of a cyanoacrylate inhibitor of Photosystem II electron transport. Z. Naturforsch. 46c:93-98.
30. Michel, H. and Deisenhofer, J. 1988. Relevance of the photosynthetic reaction center from purple bacteria to the structure of Photosystem II. Biochem. 27:1-7.
31. Mitsutake, K., H. Iwamura, R. Shimizu, and T. Fujita. 1986. Quantitative structure-activity relationship of Photosystem II inhibitors in chloroplasts and its link to herbicidal action. J. Agric. Food Chem. 34:725-732.
32. Moreland, D. E. and M. R. Boots. 1971. Effects of optically active 1-(α-methylbenzyl)-3-(3,4-dichlorophenyl)urea on reactions of mitochondria and chloroplasts. Plant Physiol. 47:53-58.
33. Pfister, K. and C. J. Amtzen. 1979. The mode of action of Photosystem II - specific inhibitors in herbicide-resistant weed biotypes. Z. Naturforsch. 34e:996-1009.
34. Phillips, J. N. 1990. Hydrophilic Photosystem II inhibitors: cyanoacrylate thiolate salts. Z. Naturforsch. 45c:343-347.
35. Soskic, M. and A. Sabljic. 1989. Inhibition of Hill reaction by 2-azido-s-triazine derivatives: QSAR study with molecular connectivity indices. Z. Naturforsch. 44c:255-261.
36. Takemoto, I., R. Yoshida, S. Sumida, and K. Kamoshita. 1984. Quantitative structure-activity relationships of substituted phenylureas on the Hill inhibitory activity. J. Pest. Sci. 9:517-521.
37. B-binding niche of Photosystem II. Z. Naturforsch. 48c:205-212.
38. Tietjen, K. G., J. F. Kluth, R. Andree, M. Haug, M. Lindig, K. H. Müller, H. J. Wroblowsky, and A. Trebst. 1991. The herbicide binding niche of Photosystem II - a model. Pestic. Sci. 31:65-72.
39. Tischer, W. and H. Strotmann. 1977. Relationship between inhibitor binding by chloroplasts and inhibition of photosynthetic electron transport. Biochim. Biophys. Acta. 460:113-125.
40. Trebst, A. 1987. The three-dimensional structure of the herbicide binding niche on the reaction center polypeptides of Photosystem II. Z. Naturforsch. 42e:742-750.
41. Wessels, J.S.C. and R. van der Veen. 1956. The action of some derivatives of phenylurethan and of 3-phenyl-1,1-dimethylurea on the Hill reaction. Biochim. Biophys. Acta. 19:548-549.
42. B-protein by photoaffinity labelling with azidoatrazine. Z. Naturforsch. 39c:425-429.
43. r 38,950. Proc. Natl. Acad. Sci. U.S.A. 79:7699-7703.