Fluridone

Fluridone
Names
IUPAC name
1-methyl-3-phenyl-5-[3-(trifluoromethyl)phenyl]pyridin-4-one
Other names
Sonar; Avast!; Whitecap
Identifiers
59756-60-4
ChemSpider 39255
Jmol 3D model Interactive image
KEGG C18857
PubChem 43079
Properties
C19H14F3NO
Molar mass 329.3 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Fluridone is an aquatic herbicide often used to control invasive plants. It is sold under the names Sonar, Avast! and Whitecap and is used in the United States to control hydrilla and Eurasian watermilfoil among other species. It is a systemic herbicide that works by interfering with carotene formation which leads to chlorophyll degradation.[1] Fluridone is sold as a liquid and as a slow release solid because the herbicide level must be maintained for several weeks.

The chemical was first reported as a possible herbicide for cotton fields in 1976.[2] It was registered with the U.S. Environmental Protection Agency in 1986 and has low toxicity to animals[3] with no restrictions on swimming or drinking in treated water bodies.[4] Fluridone breaks downs in the environment over days or weeks with the major degradation product being N-methyl formamide. The half-life of fluridone in soils and sediments is nine months.[5]

Pharmaceutical

Fluridone's main action to disrupt photosynthesis in plants is by preventing the secretion of abscisic acid.[6] As higher Eukaryotes, such as humans, also rely on an abscisic acid pathway[7] to create inflammation in normal physiological processes, fluridone can be used as an anti-inflammatory drug for humans.[8]

The FDA has listed fluridone in its list of herbicides with a dual role as a pharmaceutical.[9] Fluridone has not been evaluated for safety since this information was presented.[10] Fluridone has been banned in the EU and Japan.[11]

References

  1. ↑ Fluridone: herbicide treatment FAQ, Cornell Cooperative Extension Tompkins County, July 17, 2013
  2. ↑ 1-Methyl-3-phenyl-5-[3-(trifluoromethyl)phenyl]-4(1H)-pyridinone, a new herbicide, Thomas W. Waldrep, Harold M. Taylor, J. Agric. Food Chem., 1976, 24 (6), pp 1250–1251, DOI: 10.1021/jf60208a047, November 1976
  3. ↑ Fluridone - Human Health and Ecological Risk Assessment - Final Report, Syracuse Environmental Research Associates for USDA/Forest Service, Southern Region, November 25, 2008
  4. ↑ Report of the Food Quality Protection Act (FQPA) Tolerance Reassessment Progress and Risk Management Decision (TRED) for Fluridone, UNITED STATES ENVIRONMENTAL PROTECTION AGENCY, September 20, 2004
  5. ↑ Paranjape, Kalyani; Gowariker, Vasant; Krishnamurthy, V. N.; Gowariker, Sugha (2014-12-22). The Pesticide Encyclopedia. CABI. ISBN 9781780640143.
  6. ↑ Stetsenko, L. A.; Vedenicheva, N. P.; Likhnevsky, R. V.; Kuznetsov, V. V. (2015-04-01). "[Influence of abscisic acid and fluridone on the content of phytohormones and polyamines and the level of oxidative stress in plants of Mesembryanthemum crystallinum L. under salinity]". Izvestiia Akademii Nauk. Seriia Biologicheskaia / Rossiĭskaia Akademiia Nauk (2): 134–144. ISSN 1026-3470. PMID 26021155.
  7. ↑ Vigliarolo, Tiziana; Guida, Lucrezia; Millo, Enrico; Fresia, Chiara; Turco, Emilia; De Flora, Antonio; Zocchi, Elena (2015-05-22). "Abscisic acid transport in human erythrocytes". The Journal of Biological Chemistry 290 (21): 13042–13052. doi:10.1074/jbc.M114.629501. ISSN 1083-351X. PMC 4505561. PMID 25847240.
  8. ↑ Magnone, Mirko; Scarfì, Sonia; Sturla, Laura; Guida, Lucrezia; Cuzzocrea, Salvatore; Di Paola, Rosanna; Bruzzone, Santina; Salis, Annalisa; De Flora, Antonio (2013-11-15). "Fluridone as a new anti-inflammatory drug". European Journal of Pharmacology 720 (1-3): 7–15. doi:10.1016/j.ejphar.2013.10.058. ISSN 1879-0712. PMID 24211328.
  9. ↑ Kleinstreuer, Nicole C.; Yang, Jian; Berg, Ellen L.; Knudsen, Thomas B.; Richard, Ann M.; Martin, Matthew T.; Reif, David M.; Judson, Richard S.; Polokoff, Mark (2014-06-01). "Phenotypic screening of the ToxCast chemical library to classify toxic and therapeutic mechanisms". Nature Biotechnology 32 (6): 583–591. doi:10.1038/nbt.2914. ISSN 1546-1696. PMID 24837663.
  10. ↑ "Fluridone | Pesticides | US EPA". epa.gov. Retrieved 2015-08-26.
  11. ↑ "Herbicide". www.eoearth.org. Retrieved 2015-08-26.

External links

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