Abstracts
Sulfluramid
CAS No. 4151-50-2
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Adverse Effects

ACTIVITY: Acaricide, Insecticide (unclassified)

CAS Name: N-ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluoro-1-octanesulfonamide

Structure:

 

Violation: August 22, 2001

Largest Pesticide Penalty in New York State history - $950,000 - against S.C. Johnson for illegally distributing unsafe sulfluramid roach baits.


According to Attorney General Spitzer.
"This product was marketed for home use and was labeled as child resistant when it was not."


"... According to an EPA assessment, if a child ingested the bait, he or she could suffer irreversible reproductive damage, and boys could be rendered infertile."

Ref: August 22, 2001 Press Release. Office of the New York State Attorney General Eliot Spitzer.
http://www.fluorideaction.org/pesticides/sulfluramid.largest.fine.01.htm

December 9, 2002: In a "Significant New Use Rule" - published in the Federal Register, EPA states:

All pesticide products containing sulfluramid are under a specific timeline to be phased out by 2016. The pesticide products that are registered are for use in a variety of enclosed termite, ant, and roach bait stations. These products are pre-filled and sold only in child-resistant packaging. Products containing sulfluramid have not been registered for food or crop uses.

 

Reports available from
The National Technical Information Service
(NTIS)

Order from NTIS by: phone at 1-800-553-NTIS (U.S. customers); (703)605-6000 (other countries); fax at (703)605-6900; and email at orders@ntis.gov. NTIS is located at 5285 Port Royal Road, Springfield, VA, 22161, USA.
Order No. Title Keywords / Abstract

NTIS/OTS0001378

EPA/OTS; Doc #FYI-OTS-0701-1378

2001 - TR FR 3M SUBMITTING ADD'L HLTH & ENVIRONMNTL EFFECTS STUDIES ON PERFLUOROOCTANE SULFONATES & RELATED COMPOUNDS, WITH ATTACHMENTS AND DATED 06-28-01

Keywords:
[too many to list, but includes:]
3M CO
PERFLUOROOCTANE SULFONATES
ENVIRONMENTAL FATE

CAS Registry Numbers:

754-91-6 - Perfluorooctanesulfonamide
[C8-H2-F17-N-O2-S]

1763-23-1 - Perfluorooctane sulfonic acid
[C8-H-F17-O3-S]

4151-50-2 - Sulfluramid
[C10-H6-F17-N-O2-S]

24448-09-7 - 1-Octanesulfonamide,
1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-
heptadecafluoro-N-(2-hydroxyethyl)-N-methyl-
[C11-H8-F17-N-O3-S]

NTIS/OTS0001378

EPA/OTS; Doc #FYI-OTS-0500-1378

2000 - LETTER FROM 3M CO TO USEPA RE ADDITIONAL INFORMATION ON PERFLUOROOCTANE SULFONATES & RELATED COMPOUNDS WITH STUDIES ATTACHED & DATED 05-18-00

Keywords:
[too many to list, but includes:]
3M CO
PERFLUOROOCTANE SULFONATES
HEALTH EFFECTS

CAS Registry Numbers:

307-35-7 - Perfluorooctylsulfonyl fluoride
[C8-F18-O2-S]

376-14-7 - 2-Propenoic acid, 2-methyl-, 2-
(ethyl((heptadecafluorooctyl)sulfonyl)amino)ethyl
ester
[C16-H14-F17-N-O4-S]

754-91-6 - Perfluorooctanesulfonamide
[C8-H2-F17-N-O2-S]

1691-99-2 -Octanesulfonamide, N-ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-
heptadecafluoro-N-(2-hydroxyethyl)-
[C12-H10-F17-N-O3-S]

1763-23-1 - Perfluorooctane sulfonic acid
[C8-H-F17-O3-S]

4151-50-2 - Sulfluramid
[C10-H6-F17-N-O2-S]

24448-09-7 - 1-Octanesulfonamide,
1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-
heptadecafluoro-N-(2-hydroxyethyl)-N-methyl-
[C11-H8-F17-N-O3-S]

31506-32-8 - 1-Octanesulfonamide,
1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-
heptadecafluoro-N-methyl-
[C9-H4-F17-N-O2-S]

67584-51-4 - Glycine, N-ethyl-N-
((nonafluorobutyl)sulfonyl)-, potassium salt
[C8-H8-F9-N-O4-S.K]

86508-42-1 - Perfluoro compounds, C5-18
[Unspecified formula]

NTIS/OTS0001378

EPA/OTS; Doc #FYI-OTS-0900-1378S

2000 - SUPPORT: ADDITIONAL HEALTH & ENVIRONMENTAL EFFECTS STUDIES ON PERFLUOROOCTANE SULFONATES & RELATED COMPOUNDS, WITH COVER LETTER DATED 08-31-00 (SANITIZED)

Keywords:
[too many to list, but includes:]
3M CO
PERFLUOROOCTANE SULFONATES
ENVIRONMENTAL FATE
MONITORING
HEALTH EFFECTS
EPIDEMIOLOGY
ACUTE TOXICITY
MAMMALS

CAS Registry Numbers:

335-67-1 - Perfluorooctanoic acid (PFOA)
[C8-H-F15-O2]

355-46-4 - Perfluorohexanesulfonic acid
[C6-H-F13-O3-S]

754-91-6 - Perfluorooctanesulfonamide
[C8-H2-F17-N-O2-S]

1691-99-2 - -Octanesulfonamide, N-ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-
heptadecafluoro-N-(2-hydroxyethyl)-
[C12-H10-F17-N-O3-S]

1763-23-1 - Perfluorooctane sulfonic acid
[C8-H-F17-O3-S]

4151-50-2 - Sulfluramid
[C10-H6-F17-N-O2-S]

NTIS/PB89-235121

6p

1989 - Pesticide Fact Sheets Number 205: Sulfluramid.

Environmental Protection Agency, Washington, DC. Office of Pesticides and Toxic Substances.

The document contains up-to-date chemical information, including a summary of the Agency's regulatory position and rationale, on a specific pesticide or group of pesticides. A Fact Sheet is issued after one of the following actions has occurred: Issuance or reissuance of a registration standard, issuance of each special review document, registration of a significantly changed use pattern, registration of a new chemical, or an immediate need for information to resolve controversial issues relating to a specific chemical or use pattern.

Keywords:
Insecticides
Pesticides
Sulfluramid
Biological accumulation

 

Environ Sci Technol. 2004 Feb 1;38(3):758-62.

Biotransformation of N-ethyl perfluorooctanesulfonamide by rainbow trout (Onchorhynchus mykiss) liver microsomes.

Tomy GT, Tittlemier SA, Palace VP, Budakowski WR, Braekevelt E, Brinkworth L, Friesen K.

Department of Fisheries and Oceans, Winnipeg, Manitoba R3T 2N6, Canada. tomyg@dfo-mpo.gc.ca

Rainbow trout (Onchorhynchus mykiss) liver microsomes were incubated with N-ethyl perfluorooctanesulfonamide [N-EtPFOSA, C8F17SO2NH(C2H5)], to examine the possibility of in vitro biotransformation to perfluorooctane sulfonate (PFOS, C8F17SO3-) and perfluorooctanoate (PFOA, C7F15COO-). Incubations were performed by exposing trout liver microsomes to N-EtPFOSA at 8 degrees C in the dark. Reaction mixtures were analyzed after incubation periods of 0, 2, 4, 8, 16, and 30 h for N-EtPFOSA, PFOS, PFOA, and perfluorooctanesulfonamide (PFOSA, C8F17SO2NH2), a suspected intermediate. Amounts of PFOS and PFOSA were found to increase with incubation time, but only background levels of PFOA were detected. Three possible reaction pathways are proposed for the conversion of N-EtPFOSA to PFOS: (i) direct conversion of N-EtPFOSA to PFOS by deethylamination accompanied by conversion of the sulfone group to sulfonate, (ii) deethylation of N-EtPFOSA to PFOSA, followed by deamination to form PFOS, and (iii) direct hydrolysis of N-EtPFOSA. These findings represent the first report indicating a possible biotransformation of a perfluorosulfonamide to PFOS in fish and may help to explain the detection of PFOS, which is relatively involatile, and thus not likely to undergo atmospheric transport, in biota from remote regions.

PMID: 14968861 [PubMed - indexed for MEDLINE]


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=10227829&dopt=Abstract

No abstract available

Bull Environ Contam Toxicol 1999 May;62(5):515-9

Risk of intoxication with sulfluramid in a packing plant of Mirex-S.

Machado-Neto JG, Queiroz ME, Carvalho D, Bassini AJ.

Department of Crop Protection, School of Agricultural and Veterinary Sciences, Sao Paulo State University, Rodovia Carlos Tonanni, km 5, 14870-000, Jaboticabal, Sao Paulo, Brazil.

PMID: 10227829 [PubMed - indexed for MEDLINE]


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=1495031&dopt=Abstract

J Med Entomol 1992 Mar;29(2):207-15

Sulfluramid resistance and vapor toxicity in field-collected German cockroaches (Dictyoptera: Blattellidae).

Schal C.

Department of Entomology, Cook College, Rutgers University, New Brunswick, New Jersey 08903.

The toxicities of Raid Max Roach Bait (sulfluramid) and COMBAT Roach Control System (hydramethylnon) to susceptible and field-collected German cockroaches were examined. In all field-collected strains, a variable fraction of the population exhibited tolerance to Raid Max. In some strains, few males were killed in the first 5 d of exposure to Raid Max and some lived for up to 123 d when provided Raid Max only. Field-collected males that were given access to Raid Max for only 3 h following a 45-h starvation exhibited a 22-fold delay in mortality of 50% of the population compared with males that were continuously exposed to Raid Max. Males exposed to COMBAT for 3 h exhibited a similar pattern of mortality as males continuously exposed to this bait. Field-collected males provided COMBAT with or without rat chow exhibited identical patterns of mortality. However, males that were offered Raid Max along with rat chow exhibited significantly delayed mortality compared with males given Raid Max alone. A direct comparison of 1% hydramethylnon and sulfluramid, the active ingredients in COMBAT and Raid Max, respectively, in rat chow showed that physiological resistance to sulfluramid was involved; field-collected males consumed both baits equally on the first day, but whereas 100% of the males that were fed hydramethylnon-containing chow died within 5 d, only one of 25 males fed sulfluramid-baited rat chow died during this period, and males continued to consume large amounts of food. This suggested that, in the presence of alternate foods, the effective dose of sulfluramid was diminished, resulting in reduced mortality in males fed Raid Max.(ABSTRACT TRUNCATED AT 250 WORDS)


PMID: 1495031 [PubMed - indexed for MEDLINE]


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=1673400&dopt=Abstract

Drug Metab Dispos 1991 Jan-Feb;19(1):205-11

Metabolism and disposition of sulfluramid, a unique polyfluorinated insecticide, in the rat.

Manning RO, Bruckner JV, Mispagel ME, Bowen JM.

Department of Pharmacology & Toxicology, College of Pharmacy, University of Georgia, Athens 30602.

The objectives of this study were to characterize the absorption, distribution, and elimination of sulfluramid (N-ethyl perfluorooctane sulfonamide) and its major metabolite, perfluorooctane sulfonamide (DESFA), in order to assess the effect of dosage vehicle on their pharmacokinetics. In Trial 1, male and female Sprague-Dawley rats (170-240 g) were housed in Roth-type metabolism cages. Each rat received 50 mg/kg sulfluramid po, which contained 10 microCi of [14C] sulfluramid. Feces, urine, and expired air samples were collected for 72 hr post-dosing. Tissue samples also were collected at 72 hr and 14C distribution determined. Eighty percent of the radiolabel was eliminated within 72 hr, with the largest quantities of 14C recovered in expired air (56%) and feces (25%). Less radiolabel was recovered in urine (8%), and even smaller amounts in tissues (5%). The highest tissue concentrations of 14C were found in liver, kidneys, and adrenals, with significantly more radiolabel in the kidneys, gonads, and adrenals of the females than males. Male Sprague-Dawley rats (250-275 g) were used in Trials 2 and 3. In Trial 2, rats with a carotid artery cannula were given 50 mg/kg sulfluramid in a po bolus of polyethylene glycol 400 (PEG) or corn oil and blood samples were collected for 96 hr. In Trial 3, noncannulated rats were given 50 mg/kg sulfluramid po in PEG or corn oil and blood samples were collected from the caudal artery for 14 days. Blood samples were analyzed for sulfluramid and DESFA by gas chromatography.(ABSTRACT TRUNCATED AT 250 WORDS)

PMID: 1673400 [PubMed - indexed for MEDLINE]


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=2212234&dopt=Abstract

J Econ Entomol 1990 Aug;83(4):1409-14

Toxicity, sublethal effects, and performance of sulfluramid against the German cockroach (Dictyoptera: Blattellidae).

Appel AG, Abd-Elghafar SF.

Department of Entomology, Auburn University, Alabama 36849-5413.

Topical and oral toxicity of sulfluramid (N-ethyl perfluorooctane sulfonamide) were determined for the German cockroach, Blattella germanica (L.). The topical LD50 of sulfluramid was 175.6 micrograms/g for adult males, 117.8 micrograms/g for adult females, and 122.3 micrograms/g for gravid adult females. Ingestion increased toxicity approximately 1.4 times for adult male B. germanica. Twenty-four hours after topical treatment with 20 micrograms/insect sulfluramid, the percentage of female cockroaches that dropped their oothecae increased approximately 50% compared with controls treated with acetone. Sulfluramid also decreased oothecal hatch of both dropped and retained oothecae. Approximately 90% of oothecae from untreated females hatches, whereas less than 20% hatched from females treated with 20 micrograms/insect. Mean time for oothecal hatch increased linearly with increasing sulfluramid concentration. In arena studies in Ebeling choice boxes, LT50's ranged between approximately 2.3 and 3.9 d for a 0.331 mg/cm2 deposit and a 1.5% bait, respectively. Higher concentrations of sulfluramid were more repellent in both bait and residual formulations. Performance index values indicated excellent potential field efficacy. Field trials with 1.0 and 1.5% (AI) baits showed up to a 71.3% reduction in cockroach numbers. Baits controlled cockroaches throughout the 12-wk test.


PMID: 2212234 [PubMed - indexed for MEDLINE]


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=2331477&dopt=Abstract

Biochim Biophys Acta 1990 Apr 26;1016(3):344-8

Perfluorooctane sulfonamide: a structurally novel uncoupler of oxidative phosphorylation.

Schnellmann RG, Manning RO.

Department of Physiology and Pharmacology, College of Veterinary Medicine, University of Georgia, Athens 30602.

The effects of sulfluramide (N-ethylperfluorooctane sulfonamide) and perfluorooctane sulfonamide (DESFA) on isolated rabbit renal cortical mitochondria (RCM) were examined. Sulfluramid (1-100 microM) and DESFA (0.5-50 microM) increased state 4 respiration of RCM respiring on pyruvate/malate or succinate in a concentration dependent manner in the absence of a phosphate acceptor. In addition, both sulfluramid and DESFA increased state 4 respiration in the presence of oligomycin, an inhibitor of F0F1-ATPase. The effects of sulfluramid (200 microM), DESFA (100 microM), and the known protonophore and uncoupler of oxidative phosphorylation, carbonyl cyanide p-trifluoromethoxyphenylhydrazone (FCCP) (1 microM), on RCM proton movement were examined directly by monitoring extramitochondrial pH and indirectly by monitoring passive mitochondrial swelling. Immediately upon addition, DESFA and FCCP, but not sulfluramid, dissipated the RCM proton gradient and caused RCM to swell in solutions of NaCl or NH4Cl. These results show that DESFA uncouples oxidative phosphorylation by acting as a protonophore. RCM were shown to metabolize sulfluramid to DESFA which suggests that the increase in state 4 respiration observed with sulfluramid is due to DESFA. DESFA is unique in that it is one of two uncouplers that does not contain a ring structure and thus may be a useful model in the study of oxidative phosphorylation.

PMID: 2331477 [PubMed - indexed for MEDLINE]


From Toxline at Toxnet

1990 TOXICOL IN VITRO; 4 (1). 71-74.

The cellular effects of a unique pesticide sulfluramid (N-ethylperfluorooctanesulfonamide) on rabbit renal proximal tubules.

SCHNELLMANN RG

Dep. Physiol. and Pharmacol., Coll. Veterinary Med., Univ. Georgia, Athens, Ga. 30602, USA.

Abstract: BIOSIS COPYRIGHT: BIOL ABS. The cellular effects of sulfluramid (N-ethylperfluorooctane sulphonamide, NEPFOS) and its major metabolite perfluorooctane sulphonamide (PFOS) were examined using a suspension of rabbit renal proximal tubules as a model. NEPFOS and PFOS were potent stimulators of proximal tubule basal oxygen consumptions (QO2), with initial effects exhibited at 5-10 muM and maximal effects at 50-200 muM. The increase in basal QO2 was ouabain insensitive, which suggests that NEPFOS and PFOS may act by uncoupling oxidative phosphorylation. Exposure of tubule suspensions to NEPFOS or PFOS concentrations of 100 muM or higher for 60 min produced tubule death, indicated by an increase in the release of lactate dehyrogenase. The tubule death did not appear to result from alkylation or lipid peroxidation, since glutathione and malondialdehyde levels were unaffected. To determine the mechanism by which NEPFOS and PFOS increased tubule QO2, the effects of NEPFOS and PFOS on isolated renal cortical


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=2324377&dopt=Abstract

J Econ Entomol 1990 Feb;83(1):148-52

Topical and oral toxicity of sulfluramid, a delayed-action insecticide, against the German cockroach (Dictyoptera: Blattellidae).

Reid BL, Bennett GW, Barcay SJ.

Department of Entomology, Purdue University, West Lafayette, Indiana 47907.

The LD50 of sulfluramid topically applied to 2-d-old, fifth instars of the German cockroach, Blattella germanica (L.), was estimated at 14.5 micrograms/g (95% FL = 13.7-15.4 micrograms/g). Sulfluramid was significantly more toxic than topically applied hydramethylnon (LD50 = 29.2 [19.0-46.5] micrograms/g). Sulfluramid had delayed toxicity but caused mortality significantly faster than hydramethylnon after topical application. The oral LD50 against newly enclosed, fifth instars was estimated to be 4.1 (3.9-4.4) micrograms/g; this toxicity was significantly greater than when sulfluramid was topically applied. Mortality caused by sulfluramid occurred significantly more slowly in the dietary exposures than in the topical applications. Sulfluramid at 1,000 ppm in diets was not a feeding deterrent to nymphal B. germanica.

PMID: 2324377 [PubMed - indexed for MEDLINE]



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