Sulfluramid

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 a prodrug to the mitochondrial uncoupler (IRAC group 13) perfluorooctanesulfonamide.

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

Environmental issues

It is predominantly metabolized to perfluorooctanesulfonic acid (PFOS),^[2] but partly also to perfluorooctanoic acid (PFOA).^[3]^[4] 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.^[5]^[6]

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" (in en). Environmental Science & Technology 50 (2): 653–659. doi:10.1021/acs.est.5b04544. PMID 26653085. Bibcode: 2016EnST...50..653L.
↑ "Sulfluramid Registration Review Final Decision; Notice of Availability". 2008. https://www.federalregister.gov/documents/2008/10/29/E8-25667/sulfluramid-registration-review-final-decision-notice-of-availability.
↑ 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" (in en). Environmental Science & Technology 43 (10): 3662–3668. doi:10.1021/es803411w. PMID 19544870. Bibcode: 2009EnST...43.3662P.
↑ 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" (in en). Science of the Total Environment 580: 1247–1256. doi:10.1016/j.scitotenv.2016.12.085. PMID 28040212. Bibcode: 2017ScTEn.580.1247L. http://ir.rcees.ac.cn/handle/311016/39071.
↑ "Perfluorooctane sulfonic acid, its salts and perfluorooctane sulfonyl fluoride". 6 July 2017. https://www.pops.int/Implementation/Alternatives/AlternativestoPOPs/ChemicalslistedinAnnexB/Perfluorooctanesulfonicacidandperfluorooctane/tabid/5869/Default.aspx.
↑ 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. https://doi.org/10.1016/j.chemosphere.2023.138370.
↑ 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" (in en). Environmental Pollution 272. doi:10.1016/j.envpol.2020.115908. PMID 33190976.

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[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" (in en). Environmental Science & Technology 50 (2): 653–659. doi:10.1021/acs.est.5b04544. PMID 26653085. Bibcode: 2016EnST...50..653L.

[2] "Sulfluramid Registration Review Final Decision; Notice of Availability". 2008. https://www.federalregister.gov/documents/2008/10/29/E8-25667/sulfluramid-registration-review-final-decision-notice-of-availability.

[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" (in en). Environmental Science & Technology 43 (10): 3662–3668. doi:10.1021/es803411w. PMID 19544870. Bibcode: 2009EnST...43.3662P.

[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" (in en). Science of the Total Environment 580: 1247–1256. doi:10.1016/j.scitotenv.2016.12.085. PMID 28040212. Bibcode: 2017ScTEn.580.1247L. http://ir.rcees.ac.cn/handle/311016/39071.

[5] "Perfluorooctane sulfonic acid, its salts and perfluorooctane sulfonyl fluoride". 6 July 2017. https://www.pops.int/Implementation/Alternatives/AlternativestoPOPs/ChemicalslistedinAnnexB/Perfluorooctanesulfonicacidandperfluorooctane/tabid/5869/Default.aspx.

[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. https://doi.org/10.1016/j.chemosphere.2023.138370.

[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" (in en). Environmental Pollution 272. doi:10.1016/j.envpol.2020.115908. PMID 33190976.

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Sulfluramid

Topic: Chemistry

Environmental issues

References