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Sulfluramid

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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
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.021.801 Edit this at Wikidata
EC Number
  • 223-980-3
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • 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,2H2,1H3Key: CCEKAJIANROZEO-UHFFFAOYSA-N
SMILES
  • 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
Chemical formula C10H6F17NO2S
Molar mass 527.20 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Sulfluramid (N-EtFOSA) is a chemical compound from the group of sulfonic acid amides and per- and polyfluoroalkyl substances (PFASs) that is effective as an insecticide. It acts as an uncoupler (IRAC group 13).

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

Environmental issues

It is predominantly biotransformed to perfluorooctanesulfonic acid (PFOS), but partly also to perfluorooctanoic acid (PFOA). Sulfluramid has been banned for almost all insecticidal applications; the only use still allowed by annex B of the Stockholm Convention on Persistent Organic Pollutants is a bait to control leaf-cutting ants.

Metabolic pathways for the biotransformation of sulfluramid to PFOS

References

  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. Retrieved 2023-02-20.
  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. Retrieved 28 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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