Sulfluramide

Structural formula
General
Surname	Sulfluramide
other names	N -ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluoro-1-octanesulfonamide; N -ethyl perfluorooctane-1-sulfonamide; N -ethyl perfluorooctanesulfomamide;
Molecular formula	C 10 H 6 F 17 NO 2 S
External identifiers / databases
EC number	223-980-3
ECHA InfoCard	100.021.801
PubChem	77797
Wikidata	Q15632828
properties
Molar mass	527.20 g mol −1
Physical state	firmly
Melting point	96 ° C
boiling point	196 ° C
Vapor pressure	0.0057 mPa (25 ° C)
solubility	almost insoluble in water, soluble in methanol
safety instructions
H and P phrases	H: 302-312-411
	P: 273-280
Toxicological data	543 mg kg −1 ( LD 50 , rat , oral ) ; > 2000 mg kg −1 ( LD 50 , rabbit , transdermal ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Sulfluramide is a chemical compound from the group of sulfonic acid amides and per- and polyfluorinated alkyl compounds (PFAS) that is effective as an insecticide . It is mainly broken down to perfluorooctane sulfonate (PFOS), but can also be converted into PFOA .

Extraction and presentation

Sulfluramide is made by reacting perfluorooctanesulfonyl fluoride and ethylamine .

use

The compound is used in bait cans to fight ants , cockroaches and termites .

Admission

Sulfluramide is not contained in plant protection products that are approved in Germany, Austria or Switzerland. There is no entry for this compound in the EU plant protection product database.

The last product approvals in the USA expired at the end of 2012, the sell-off periods ended at the end of 2013. Sulfluramide is still used in Brazil. Annual production increased from around 30 tons in 2003 to 60 tons in 2013.

Individual evidence

↑ ^a ^b ^c ^d Robert Krieger (Ed.): Hayes' Handbook of Pesticide Toxicology, Volume 1 . Elsevier, 1999, ISBN 978-0-12-374367-1 , pp. 753 ( limited preview in Google Book search).
↑ ^a ^b data sheet Sulfluramid, analytical standard from Sigma-Aldrich , accessed on October 18, 2016 ( PDF ).
↑ ^a ^b US-EPA Pesticides: Sulfluramid (PDF; 277 kB).
↑ ^a ^b Sulfluramid Registration Review Final Decision; Notice of Availability. October 29, 2008, accessed October 21, 2019 .
↑ Megan H. Plumlee, Kristopher McNeill, Martin Reinhard: Indirect Photolysis of Perfluorochemicals: Hydroxyl Radical-Initiated Oxidation of N-Ethyl Perfluorooctane Sulfonamido Acetate (N-EtFOSAA) and Other Perfluoroalkanesulfonamides. In: Environmental Science & Technology . 43, 2009, pp. 3662-3668, doi: 10.1021 / es803411w .
↑ Zhaoyang Liu, Yonglong Lu, Pei Wang, Tieyu Wang, Shijie Liu, Andrew C. Johnson, Andrew J. Sweetman, Yvette Baninla: Pollution pathways and release estimation of perfluorooctane sulfonate (PFOS) and perfluorooctanoic acid (PFOA) in central and eastern China. In: Science of The Total Environment . 580, 2017, pp. 1247–1256, doi: 10.1016 / j.scitotenv.2016.12.085 .
↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 984 .
^ Directorate-General for Health and Food Safety of the European Commission: EU pesticide database ; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; Retrieved February 19, 2016.
↑ PIC LIST - CITRUS INTEGRATED PRODUCTION ( Memento from March 4, 2016 in the Internet Archive )
↑ John Löfstedt Gilljam, Juliana Leonel, Ian T. Cousins, Jonathan P. Benskin: Is Ongoing Sulfluramid Use in South America a Significant Source of Perfluorooctanesulfonate (PFOS)? Production Inventories, Environmental Fate, and Local Occurrence. In: Environmental Science & Technology. 50, 2016, pp. 653-659, doi: 10.1021 / acs.est.5b04544 .

[hayes-1] Robert Krieger (Ed.): Hayes' Handbook of Pesticide Toxicology, Volume 1 . Elsevier, 1999, ISBN 978-0-12-374367-1 , pp. 753 ( limited preview in Google Book search).

[Sigma-2] ta sheet Sulfluramid, analytical standard from Sigma-Aldrich , accessed on October 18, 2016 ( PDF ).

[epa-3] US-EPA Pesticides: Sulfluramid (PDF; 277 kB).

[epa_final-4] Sulfluramid Registration Review Final Decision; Notice of Availability. October 29, 2008, accessed October 21, 2019 .

[5] Megan H. Plumlee, Kristopher McNeill, Martin Reinhard: Indirect Photolysis of Perfluorochemicals: Hydroxyl Radical-Initiated Oxidation of N-Ethyl Perfluorooctane Sulfonamido Acetate (N-EtFOSAA) and Other Perfluoroalkanesulfonamides. In: Environmental Science & Technology . 43, 2009, pp. 3662-3668, doi: 10.1021 / es803411w .

[6] Zhaoyang Liu, Yonglong Lu, Pei Wang, Tieyu Wang, Shijie Liu, Andrew C. Johnson, Andrew J. Sweetman, Yvette Baninla: Pollution pathways and release estimation of perfluorooctane sulfonate (PFOS) and perfluorooctanoic acid (PFOA) in central and eastern China. In: Science of The Total Environment . 580, 2017, pp. 1247–1256, doi: 10.1016 / j.scitotenv.2016.12.085 .

[unger-7] Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 984 .

[8] Directorate-General for Health and Food Safety of the European Commission: EU pesticide database ; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; Retrieved February 19, 2016.

[9] PIC LIST - CITRUS INTEGRATED PRODUCTION ( Memento from March 4, 2016 in the Internet Archive )

[10] John Löfstedt Gilljam, Juliana Leonel, Ian T. Cousins, Jonathan P. Benskin: Is Ongoing Sulfluramid Use in South America a Significant Source of Perfluorooctanesulfonate (PFOS)? Production Inventories, Environmental Fate, and Local Occurrence. In: Environmental Science & Technology. 50, 2016, pp. 653-659, doi: 10.1021 / acs.est.5b04544 .