Fluridone

Fluridone

Names
IUPAC name 1-methyl-3-phenyl-5-[3-(trifluoromethyl)phenyl]pyridin-4-one
Other names Sonar; Avast!; Whitecap
Identifiers
CAS Number	59756-60-4
3D model (Jmol)	Interactive image
ChemSpider	39255
ECHA InfoCard	100.056.269
KEGG	C18857
PubChem	43079
InChI InChI=1S/C19H14F3NO/c1-23-11-16(13-6-3-2-4-7-13)18(24)17(12-23)14-8-5-9-15(10-14)19(20,21)22/h2-12H,1H3 Key: YWBVHLJPRPCRSD-UHFFFAOYSA-N InChI=1/C19H14F3NO/c1-23-11-16(13-6-3-2-4-7-13)18(24)17(12-23)14-8-5-9-15(10-14)19(20,21)22/h2-12H,1H3 Key: YWBVHLJPRPCRSD-UHFFFAOYAR
SMILES CN1C=C(C(=O)C(=C1)C2=CC(=CC=C2)C(F)(F)F)C3=CC=CC=C3
Properties
Chemical formula	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]

Molecular target

Fluridone and Norflurazon are inhibitors of chloroplastic and cyanobacterial Phytoene desaturase, which in turn disrupts the carotenoid biosynthetic pathway.

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, in theory, could be used at rates greatly exceeding current EPA maximum concentration levels in the environment, as an anti-inflammatory agent for humans.^[8] The molecular target of Fluridone in in humans is however unknown, since animals lack carotenoid biosynthesis.

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.

External links

• EPA Substance Registry, entry for Fluridone
• BREDA list of 1,5-Cis-Phytoene desaturase inhibitors