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 -EthylperfluorooctylsulfonamideN -Ethylheptadecafluorooctanesulfonamide
Identifiers
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
100.021.801
EC Number
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
C 10 H 6 F 17 N O 2 S
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).
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 .
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 .