Sulfluramid

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	4151-50-2 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:81945;
ChEMBL	ChEMBL177726;
ChemSpider	70194;
ECHA InfoCard	100.021.801
EC Number	223-980-3;
KEGG	C18766;
PubChem CID	77797;
UNII	IPX089YR0A;
CompTox Dashboard (EPA)	DTXSID1032646 ;
	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,2H2,1H3 Key: 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−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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.

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

Environmental issues

It is predominantly biotransformed to perfluorooctanesulfonic acid (PFOS),^[2] but partly also to perfluorooctanoic acid (PFOA).^[3]^[4] Sulfluramid benefits from an acceptable purpose in the listing of PFOS to annex B of the Stockholm Convention on Persistent Organic Pollutants.

Metabolic pathways for the biotransformation of sulfluramid to PFOS^[5]

References

^ 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.
^ "Sulfluramid Registration Review Final Decision; Notice of Availability". unblock.federalregister.gov. 2008. Retrieved 2023-02-20.
^ 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.
^ 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.
^ 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.

[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] 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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