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 (JSmol)	Interactive image;
ChemSpider	39255;
ECHA InfoCard	100.056.269
KEGG	C18857;
PubChem CID	43079;
UNII	3L0JQA61JX ;
CompTox Dashboard (EPA)	DTXSID8024107 ;
	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 FC(F)(F)c1cccc(c1)-c2cn(C)cc(c2=O)-c3ccccc3;
Properties
Chemical formula	C19H14F3NO
Molar mass	329.3 g/mol
Appearance	colorless solid
Melting point	154.5 °C (310.1 °F; 427.6 K)
	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 organic compound that is used as aquatic herbicide often used to control invasive plants. It is used in the United States to control hydrilla and Eurasian watermilfoil among other species. Fluridone is sold as a solution and as a slow release solid because the herbicide level must be maintained for several weeks. The compound is a colorless solid.[1]

The compound 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 down 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 is a systemic herbicide that works by interfering with carotene formation which leads to chlorophyll degradation.[6] 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.[7] As higher eukaryotes, such as humans, also rely on an abscisic acid pathway[8] to create inflammation in normal physiological processes, fluridone could be investigated as being of interest in the development of anti-inflammatory agents.[9]

Biodegradation

Fluridone degrades in soil and upon exposure to sunlight with approximate halflives of 21 and 1 day, respectively.[1]

References

Franz Müller and Arnold P. Applebyki "Weed Control, 2. Individual Herbicides" in Ullmann's Encyclopedia of Industrial Chemistry 2010 doi:10.1002/14356007.o28_o01
Waldrep, Thomas W.; Taylor, Harold M. (1976). "1-Methyl-3-phenyl-5-[3-(trifluoromethyl)phenyl]-4(1H)-pyridinone, a new herbicide". Journal of Agricultural and Food Chemistry. 24 (6): 1250–1251. doi:10.1021/jf60208a047. PMID 1002909.
Fluridone - Human Health and Ecological Risk Assessment - Final Report, Syracuse Environmental Research Associates for USDA/Forest Service, Southern Region, November 25, 2008
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
Paranjape, Kalyani; Gowariker, Vasant; Krishnamurthy, V. N.; Gowariker, Sugha (2014-12-22). The Pesticide Encyclopedia. CABI. ISBN 9781780640143.
Fluridone: herbicide treatment FAQ, Cornell Cooperative Extension Tompkins County, July 17, 2013
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.
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.
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

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[Ullmanns-1] Franz Müller and Arnold P. Applebyki "Weed Control, 2. Individual Herbicides" in Ullmann's Encyclopedia of Industrial Chemistry 2010 doi:10.1002/14356007.o28_o01

[2] Waldrep, Thomas W.; Taylor, Harold M. (1976). "1-Methyl-3-phenyl-5-[3-(trifluoromethyl)phenyl]-4(1H)-pyridinone, a new herbicide". Journal of Agricultural and Food Chemistry. 24 (6): 1250–1251. doi:10.1021/jf60208a047. PMID 1002909.

[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] Fluridone: herbicide treatment FAQ, Cornell Cooperative Extension Tompkins County, July 17, 2013

[7] 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.

[8] 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.

[9] 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.