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Amicarbazone, a New Photosystem II Inhibitor

Published online by Cambridge University Press:  20 January 2017

Franck E. Dayan ,
Maria L. B. Trindade  and
Edivaldo D. Velini
Franck E. Dayan*
Affiliation:
USDA-ARS, Natural Products Utilization Research Unit, P.O. Box 8048, University, MS 38677
Maria L. B. Trindade
Affiliation:
São Paulo State University, Faculty of Agronomic Sciences, Botucatu, Brazil
Edivaldo D. Velini
Affiliation:
São Paulo State University, Faculty of Agronomic Sciences, Botucatu, Brazil
*
Corresponding author's E-mail: fdayan@olemiss.edu
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Abstract

Amicarbazone is a new triazolinone herbicide with a broad spectrum of weed control. The phenotypic responses of sensitive plants exposed to amicarbazone include chlorosis, stunted growth, tissue necrosis, and death. Its efficacy as both a foliar- and root-applied herbicide suggests that absorption and translocation of this compound is very rapid. This new herbicide is a potent inhibitor of photosynthetic electron transport, inducing chlorophyll fluorescence and interrupting oxygen evolution ostensibly via binding to the QB domain of photosystem II (PSII) in a manner similar to the triazines and the triazinones classes of herbicides. As a result, its efficacy is susceptible to the most common form of resistance to PSII inhibitors. Nonetheless, amicarbazone has a good selectivity profile and is a more potent herbicide than atrazine, which enables its use at lower rates than those of traditional photosynthetic inhibitors.

Keywords

Amicarbazonephotosystem inhibitor, CAS No. 129909-90-6, BAY MKH 3586atrazine, CAS No. 1912-24-9.Herbicide mode of actionphotosynthesisphotosystem IIherbicide resistance
Type
Physiology, Chemistry, and Biochemistry
Information
Weed Science , Volume 57 , Issue 6 , December 2009 , pp. 579 - 583
Copyright
Copyright © Weed Science Society of America 

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References

Literature Cited

Anderson, M. P. and Gronwald, J. W. 1991. Atrazine resistance in a velvetleaf (Abutilon theophrasti) biotype due to enhanced glutathione-S-transferase activity. Plant Physiol. 96:104–109.CrossRefGoogle Scholar
Cavenaghi, A. L., Rossi, C. V. S., Negrisoli, E., Costa, E. A. D., Velini, E. D., and Toledo, R. E. B. 2007. Performance of amicarbazone applied on sugarcane straw. Planta Daninha. 25:831–837.CrossRefGoogle Scholar
Dayan, F. E., Armstrong, B. M., and Weete, J. D. 1998. Inhibitory activity of sulfentrazone and its metabolic derivatives on soybean (Glycine max) protoporphyrinogen oxidase. J. Agric. Food Chem. 46:2024–2029.CrossRefGoogle Scholar
Dayan, F. E., Duke, S. O., Weete, J. D., and Hancock, H. G. 1997a. Selectivity and mode of action of carfentrazone-ethyl, a novel phenyl triazolinone herbicide. Pestic. Sci. 51:65–73.3.0.CO;2-9>CrossRefGoogle Scholar
Dayan, F. E., Green, H. M., Weete, J. D., and Hancock, H. G. 1996. Postemergence activity of sulfentrazone: effects of surfactants and leaf surfaces. Weed Sci. 44:797–803.CrossRefGoogle Scholar
Dayan, F. E., Howell, J. L., and Weidenhamer, J. D. 2009. Dynamic root exudation of sorgoleone and its in planta mechanism of action. J. Exp. Bot. 60:2107–2117.CrossRefGoogle ScholarPubMed
Dayan, F. E., Weete, J. D., Duke, S. O., and Hancock, H. G. 1997b. Soybean (Glycine max) cultivar differences in response to sulfentrazone. Weed Sci. 45:634–641.Google Scholar
Draber, W., Tietjen, K., Kluth, J. F., and Trebst, A. 1991. Herbicides in photosynthesis research. Ang. Chem. Int. Ed. 30:1621–1633.CrossRefGoogle Scholar
Draber, W., Trebst, A., and Oettmeier, W. 1995. Structure-activity relationships of quinone and acridone photosystem II inhibitors. Pages 186–198. In Hansch, C. and Fujita, T. Classical and Three-Dimensional QSAR in Agrochemistry. American Chemical Society Symposium Series. Washington, DC American Chemical Society.Google Scholar
Heap, I. 2009. International survey of herbicide resistant weeds. www.weedscience.com. Accessed: May 1, 2009.Google Scholar
Hess, F. D. 2000. Light-dependent herbicides: An overview. Weed Sci. 48:160–170.CrossRefGoogle Scholar
Kinoshita, I., Sanbe, A., and Yokomura, E. I. 2008. Difference in light-induced increase in ploidy level and cell size between adaxial and abaxial epidermal pavement cells of Phaseolus vulgaris primary leaves. J. Exp. Bot. 59:1419–1430.CrossRefGoogle ScholarPubMed
Luo, Y. P., Jiang, L. L., Wang, G. D., Chen, Q., and Yang, G. F. 2008. Syntheses and herbicidal activities of novel triazolinone derivatives. J. Agric. Food Chem. 56:2118–2124.CrossRefGoogle ScholarPubMed
Mueller, K. H. 2002. BAY MKH 6561—propoxycarbazone-sodium a new grass herbicide for cereal growing. Pflanzenschutz-Nachr. Bayer. 55:15–28.Google Scholar
Negrisoli, E., Rossi, C. V. S., Velini, E. D., Cavenaghi, A. L., Costa, E. A. D., and Toledo, R. E. B. 2007. Weed control by amicarbazone applied in the presence of sugar-cane straw. Planta Daninha. 25:603–611.CrossRefGoogle Scholar
Oettmeier, W. 1999. Herbicide resistance and supersensitivity in photosystem II. Cell. Mol. Life Sci. 55:1255–1277.CrossRefGoogle ScholarPubMed
Philbrook, B. D., Kremer, M., Mueller, K. H., and Deege, R. 1999. BAY MKH 3586—a new herbicide for broad spectrum weed control in corn (maize) and sugar cane. Brighton Conference. Weeds. 1:29–34.Google Scholar
R-Development-Core-Team 2009. R: A language and environment for statistical computing. Vienna, Áustria R Foundation for Statistical Computing.Google Scholar
Rimando, A. M., Dayan, F. E., Czarnota, M. A., Weston, L. A., and Duke, S. O. 1998. A new photosystem II electron transfer inhibitor from Sorghum bicolor . J. Nat. Prod. 61:927–930.CrossRefGoogle ScholarPubMed
Ritz, C. and Streibig, J. C. 2005. Bioassay analysis using R. J. Statist. Soft. 12:1–22.CrossRefGoogle Scholar
Ryan, G. F. 1970. Resistance of common groundsel to simazine and atrazine. Weed Sci. 18:614–616.CrossRefGoogle Scholar
Seeruttun, S., Barbe, C., and Gaungoo, A. 2008. New herbicide tank-mix, Krismat + Dinamic: a cost-effective broad-spectrum pre- & post-emergence treatment for managing weeds in sugarcane. Sugar Cane Internat. 26:18–21.Google Scholar
Senseman, S. A. 2007. Herbicide Handbook. Lawrence, KS Weed Science Society of America.Google Scholar
Shimabukuro, R. H., Frear, D. S., Swanson, H. R., and Walsh, W. C. 1971. Glutathione conjugation: an enzymatic basis for atrazine resistance in corn. Plant Physiol. 47:10–14.CrossRefGoogle ScholarPubMed
Sobolev, V. and Edelman, M. 1995. Modeling of quinone-B binding site of the photosystem II reaction center using notions of complementarity and contact-surface between atoms. Proteins. 21:214–225.CrossRefGoogle ScholarPubMed
Theodoridis, G., Baum, J. S., Hotzman, F. W., Manfredi, M. C., Maravetz, L. L., Lyga, J. W., Tymonko, J. M., Wilson, K. R., Poss, K. M., and Wyle, M. J. 1992. Synthesis and herbicidal properties of aryltriazolinones: a new class of pre- and postemergence herbicides. American Chemical Society Symposium Series. Washington, DC American Chemical Society.CrossRefGoogle Scholar
Trebst, A. 2007. Inhibitors in the functional dissection of the photosynthetic electron transport system. Photosynth. Res. 92:217–224.CrossRefGoogle ScholarPubMed
Trebst, A. and Draber, W. 1986. Inhibitors of photosystem II and the topology of the herbicide and QB binding polypeptide in the thylakoid membrane. Photosynth. Res. 10:381–392.CrossRefGoogle ScholarPubMed