Fluridone
{{for|the antiviral drug|fluridine}}
{{Chembox
| ImageFile = Fluridone.svg
| OtherNames = Sonar; Avast!; Whitecap
| PIN = 1-Methyl-3-phenyl-5-[3-(trifluoromethyl)phenyl]pyridin-4(1H)-one
| Section1 = {{Chembox Identifiers
| PubChem = 43079
| CASNo = 59756-60-4
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 3L0JQA61JX
| SMILES = FC(F)(F)c1cccc(c1)-c2cn(C)cc(c2=O)-c3ccccc3
| ChemSpiderID = 39255
| 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
| InChIKey = YWBVHLJPRPCRSD-UHFFFAOYAR
| StdInChI = 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
| StdInChIKey = YWBVHLJPRPCRSD-UHFFFAOYSA-N
| RTECS =
| MeSHName =
| ChEBI =
| KEGG = C18857}}
| Section2 = {{Chembox Properties
| Formula = C19H14F3NO
| MolarMass = 329.3 g/mol
| Appearance = colorless solid
| Density =
| MeltingPtC = 154.5
| BoilingPt =
| Solubility = }}
| Section3 = {{Chembox Hazards
| MainHazards =
| FlashPtC = }}
}}
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.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}}
The compound was first reported as a possible herbicide for cotton fields in 1976.{{cite journal|doi=10.1021/jf60208a047 | pmid=1002909 | volume=24 | issue=6 | title=1-Methyl-3-phenyl-5-[3-(trifluoromethyl)phenyl]-4(1H)-pyridinone, a new herbicide | year=1976 | journal=Journal of Agricultural and Food Chemistry | pages=1250–1251 | last1 = Waldrep | first1 = Thomas W. | last2 = Taylor | first2 = Harold M.}} It was registered with the U.S. Environmental Protection Agency in 1986 and has low toxicity to animals[http://www.fs.fed.us/foresthealth/pesticide/pdfs/0521002a_Fluridone.pdf Fluridone - Human Health and Ecological Risk Assessment - Final Report], Syracuse Environmental Research Associates for USDA/Forest Service, Southern Region, November 25, 2008 with no restrictions on swimming or drinking in treated water bodies.[http://www.epa.gov/oppsrrd1/REDs/fluridone_tred.pdf 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 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 has been estimated at nine months.{{Cite book|title = The Pesticide Encyclopedia|url = https://books.google.com/books?id=cnDHBgAAQBAJ|publisher = CABI|date = 2014-12-22|isbn = 9781780640143|language = en|first1 = Kalyani|last1 = Paranjape|first2 = Vasant|last2 = Gowariker|first3 = V. N.|last3 = Krishnamurthy|first4 = Sugha|last4 = Gowariker}} Fluridone degradation in soil and saturated sediment has been correlated with temperature and clay content, while fluridone degradation in water is largely dependent on UV light exposure.{{cite journal|doi=10.1016/j.envpol.2020.114750 | volume=265 | title=UV light and temperature induced fluridone degradation in water and sediment and potential transport into aquifer | year=2020 | journal=Environmental Pollution | pages=114750 | last1 = Wickham | first1 = Patrick | last2 = Pandey | first2 = Pramod | last3 = Harter | first3 = Thomas| last4 = Sandoval-Solis | first4 = Samuel.| issue=Pt A | pmid=32454379 | s2cid=218908634 }} Fluridone transport through the soil, vadose zone, and aquifer is limited by its strong sorbance to organic matter.
Molecular target
Fluridone is a systemic herbicide that works by interfering with carotene formation which leads to chlorophyll degradation.[http://ccetompkins.org/environment/invasive-species/fluridone-herbide-treatment-faq Fluridone: herbicide treatment FAQ], Cornell Cooperative Extension Tompkins County, July 17, 2013 Fluridone and {{Interlanguage link multi|Norflurazon|de}} 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.{{Cite journal|title = [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]|journal = Izvestiia Akademii Nauk. Seriia Biologicheskaia|date = 2015-04-01|issn = 1026-3470|pmid = 26021155|pages = 134–144|issue = 2|first1 = L. A.|last1 = Stetsenko|first2 = N. P.|last2 = Vedenicheva|first3 = R. V.|last3 = Likhnevsky|first4 = V. V.|last4 = Kuznetsov| volume=42 | doi=10.1134/S1062359015020107 | bibcode=2015BioBu..42...98S | s2cid=254277868 }} As higher eukaryotes, such as humans, also rely on an abscisic acid pathway{{Cite journal|title = Abscisic acid transport in human erythrocytes|journal = The Journal of Biological Chemistry|date = 2015-05-22|issn = 1083-351X|pmc = 4505561|pmid = 25847240|pages = 13042–13052|volume = 290|issue = 21|doi = 10.1074/jbc.M114.629501|first1 = Tiziana|last1 = Vigliarolo|first2 = Lucrezia|last2 = Guida|first3 = Enrico|last3 = Millo|first4 = Chiara|last4 = Fresia|first5 = Emilia|last5 = Turco|first6 = Antonio|last6 = De Flora|first7 = Elena|last7 = Zocchi|doi-access = free}} to create inflammation in normal physiological processes, fluridone could be investigated as being of interest in the development of anti-inflammatory agents.{{Cite journal|title = Fluridone as a new anti-inflammatory drug|journal = European Journal of Pharmacology|date = 2013-11-15|issn = 1879-0712|pmid = 24211328|pages = 7–15|volume = 720|issue = 1–3|doi = 10.1016/j.ejphar.2013.10.058|first1 = Mirko|last1 = Magnone|first2 = Sonia|last2 = Scarfì|first3 = Laura|last3 = Sturla|first4 = Lucrezia|last4 = Guida|first5 = Salvatore|last5 = Cuzzocrea|first6 = Rosanna|last6 = Di Paola|first7 = Santina|last7 = Bruzzone|first8 = Annalisa|last8 = Salis|first9 = Antonio|last9 = De Flora|url = https://zenodo.org/record/896076|doi-access = free}}
Biodegradation
See also
- Stormy Lake (Alaska), a lake that was treated with fluridone to remove invasive Elodea, an aquatic plant.
References
{{reflist}}
External links
- [http://iaspub.epa.gov/sor_internet/registry/substreg/searchandretrieve/advancedsearch/search.do;jsessionid=MY2xSxNWv24xp0gR1VMXPtGgKJYSy3SbsN543NpFq5nGnMFsmTB2!51709983?details=displayDetails EPA Substance Registry], entry for Fluridone
- [http://www.brenda-enzymes.org/enzyme.php?ecno=1.3.5.5#INHIBITORS BREDA list of 1,5-Cis-Phytoene desaturase inhibitors]
Category:Trifluoromethyl compounds