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Sulfluramid

From Wikipedia, the free encyclopedia
Sulfluramid
Names
IUPAC name
N-ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonamide
Other names
N-Ethylperfluorooctylsulfonamide
N-Ethylheptadecafluorooctanesulfonamide
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard100.021.801Edit this at Wikidata
EC Number
  • 223-980-3
KEGG
UNII
  • InChI=1S/C10H6F17NO2S/c1-2-28-31(29,30)10(26,27)8(21,22)6(17,18)4(13,14)3(11,12)5(15,16)7(19,20)9(23,24)25/h28H,2H2,1H3
    Key: CCEKAJIANROZEO-UHFFFAOYSA-N
  • CCNS(=O)(=O)C(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F
Properties
C10H6F17NO2S
Molar mass527.20 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Sulfluramid (N-EtFOSA) is a chemical compound from the group of sulfonic acid amides andper- and polyfluoroalkyl substances (PFASs) that is effective as aninsecticide. It acts as aprodrug to themitochondrial uncoupler (IRAC group 13)perfluorooctanesulfonamide.

Annual production increased from about 30 tons in 2003 to 60 tons in 2013.[1]

Environmental issues

[edit]

It is predominantly metabolized toperfluorooctanesulfonic acid (PFOS),[2] but partly also toperfluorooctanoic acid (PFOA).[3][4] Sulfluramid has been banned for almost all insecticidal applications; the only use still allowed by annex B of theStockholm Convention on Persistent Organic Pollutants is a bait to control leaf-cutting ants.[5][6]

Metabolism of sulfluramid.[7]

References

[edit]
  1. ^Löfstedt Gilljam, John; Leonel, Juliana; Cousins, Ian T.; Benskin, Jonathan P. (2016-01-19). "Is Ongoing Sulfluramid Use in South America a Significant Source of Perfluorooctanesulfonate (PFOS)? Production Inventories, Environmental Fate, and Local Occurrence".Environmental Science & Technology.50 (2):653–659.Bibcode:2016EnST...50..653L.doi:10.1021/acs.est.5b04544.PMID 26653085.
  2. ^"Sulfluramid Registration Review Final Decision; Notice of Availability".unblock.federalregister.gov. 2008. Retrieved2023-02-20.
  3. ^Plumlee, Megan H.; McNeill, Kristopher; Reinhard, Martin (2009-05-15). "Indirect Photolysis of Perfluorochemicals: Hydroxyl Radical-Initiated Oxidation of N-Ethyl Perfluorooctane Sulfonamido Acetate (N-EtFOSAA) and Other Perfluoroalkanesulfonamides".Environmental Science & Technology.43 (10):3662–3668.Bibcode:2009EnST...43.3662P.doi:10.1021/es803411w.PMID 19544870.
  4. ^Liu, Zhaoyang; Lu, Yonglong; Wang, Pei; Wang, Tieyu; Liu, Shijie; Johnson, Andrew C.; Sweetman, Andrew J.; Baninla, Yvette (February 2017)."Pollution pathways and release estimation of perfluorooctane sulfonate (PFOS) and perfluorooctanoic acid (PFOA) in central and eastern China".Science of the Total Environment.580:1247–1256.Bibcode:2017ScTEn.580.1247L.doi:10.1016/j.scitotenv.2016.12.085.PMID 28040212.
  5. ^"Perfluorooctane sulfonic acid, its salts and perfluorooctane sulfonyl fluoride".Stockholm Convention on Persistent Organic Pollutants (POPs). 6 July 2017. Retrieved28 December 2024.
  6. ^Guida, Yago; Torres, F´abio Barbosa Machado; Barizon, Robson Rolland Monticelli; Assalin, Marcia Regina; Rosa, Maria Aparecida (2023)."Confirming sulfluramid (EtFOSA) application as a precursor of perfluorooctanesulfonic acid (PFOS) in Brazilian agricultural soils".Chemosphere.325: 138370.
  7. ^Zhang, Wenping; Pang, Shimei; Lin, Ziqiu; Mishra, Sandhya; Bhatt, Pankaj; Chen, Shaohua (March 2021). "Biotransformation of perfluoroalkyl acid precursors from various environmental systems: advances and perspectives".Environmental Pollution.272 115908.doi:10.1016/j.envpol.2020.115908.PMID 33190976.S2CID 226973891.
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