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N-Ethylheptadecafluoroctansulfonamid

Volcano

HCID 77797
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Grundinformationen

CAS
4151-50-2
Standard-SMILES
CCNS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F
InChIKey
CCEKAJIANROZEO-UHFFFAOYSA-N
Summenformel
C8F17SO2NHC2H5
Durchschnittliche Molmasse
527,2 g/mol
Monoisotopische Masse
526,9847784

Überblick

Sulfluramid is a sulfonamide obtained by the formal condensation of perfluorooctane-1-sulfonic acid with ethylamine. It has a role as an acaricide, an insecticide, a xenobiotic and an environmental contaminant. It is functionally related to an ethylamine and a perfluorooctane-1-sulfonic acid.

Namen und Bezeichner

Bevorzugter Name
Volcano
IUPAC
N-ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonamide
Lokaler Name
N-Ethylheptadecafluoroctansulfonamid
Englischer Name
Sulfluramid
Summenformel
C10H6F17NO2S
Molmasse
527.2

Namen und Synonyme

Sulfluramid4151-50-2N-EthylperfluorooctanesulfonamideFinitronN-ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonamideMirex SAlstar (pesticide)N-EthylperfluorooctylsulfonamideVolcano (insecticide)GX 071AI 3-29757N-Ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluoro-1-octanesulfonamide
Weitere Namen anzeigen
SulfluramideN-ETHYL PERFLUOROOCTANESULFONAMIDEN-Ethyl-n-perfluorooctanesulfonamideFC-9FX 12gx071AlstarRK-8111
IPX089YR0AGX-071BRN 2317462AI3-29757N-ethylperfluorooctane-1-sulfonamideCHEBI:81945VolcanoN-ethyl(perfluorooctane)sulfonamide

Datenbank-Bezeichner

CAS
4151-50-2

Eigenschaften

Berechnete Struktureigenschaften

XLogP
5,6
Polarare Oberfläche (TPSA)
54,6 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
20
Frei drehbare Bindungen
9
Schwere Atome
31
Formalladung
0
Komplexität
763

Experimentelle und physikochemische Eigenschaften

PFAS · 6 Einträge

PFAS -> Perfluoroalkylsulfonamides

PFAS

PFAS -> Perfluoroalkane sulfonyl fluoride (PASF)-based substances

PFAS -> PFAS with analytical method available

PFAS -> PFalkylsulfonamides (FASA)

PFAS -> Other/unspecified

pHVery weak acid
PesticidesPesticides -> Other Insecticides
LogPlog Kow >6.80 (un-ionized)
Color/Form · 2 Einträge

Colorless crystals

Brown crystals

Solubility · 2 Einträge

Insoluble in water at 25 °C

Solubility in dichloromethane 18.6, hexane 1.4, methanol 833 (all in g/L)

Boiling Point196 °C
Melting Point · 2 Einträge

96 °C

MP: 87-93 °C /Technical/

Vapor Pressure · 2 Einträge

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 4 Einträge

Warning

H302+H312 (98.5%): Harmful if swallowed or in contact with skin [Warning Acute toxicity, oral; acute toxicity, dermal]

P264, P270, P273, P280, P301+P317, P302+P352, P317, P321, P330, P362+P364, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 68 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory Information · 2 Einträge

S - indicates a substance that is identified in a final Significant New Use Rule.

Substance: N-ethylheptadecafluorooctanesulphonamide

Hazards SummaryNot mutagenic; A mild skin irritant; [HSDB] Causes weight loss in high-dose oral studies of mice; [RTECS] A mild skin irritant; [MSDSonline]
TSCA Requirements · 1 Eintrag

Certain perfluoroalkyl sulfonates. (a) Chemical substances and significant new uses subject to reporting. (1) The chemical substances listed /including 1-Octanesulfonamide, N-ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluoro-/ ... are subject to reporting under this section for the significant new uses described in paragraph (a)(2) of this section. ... (2) The significant new uses are: ... (ii) Any manufacture or import for any use ... except as noted in paragraph (a)(3) of this section. ... (a)(3) Manufacture or import ... for the following specific uses shall not be considered as a significant new use subject to reporting under this section: (i) Use as an anti-erosion additive in fire-resistant phosphate ester aviation hydraulic fluids. (ii) Use as a component of a photoresist substance, including a photo acid generator or surfactant, or as a component of an anti-reflective coating, used in a photomicrolithography process to produce semiconductors or similar components of electronic or other miniaturized devices. (iii) Use in coating for surface tension, static discharge, and adhesion control for analog and digital imaging films, papers, and printing plates, or as a surfactant in mixtures used to process imaging films. (iv) Use as an intermediate only to produce other chemical substances to be used solely for the uses listed in paragraph (a)(3)(i), (ii), or (iii) of this section.

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 1 Eintrag

An investigation of the pharmacokinetics and toxicokinetics of N-ethylperfluorooctanesulfonamide (GX-071), in support of its registration as a pesticide for use against the red imported fire ant, was presented. GX-071 and its major metabolite, perfluorooctanesulfonamide (GX-071M) were identified in the blood of rats and dogs that had been given oral doses of GX-071. This methodology included the separation of an ethyl-acetate extract of whole blood by cold on column injection capillary gas chromatography. Capillary gas chromatography/mass spectrometry was used to confirm the identification of both GX-071 and GX-071M in a 40 microliter sample of blood taken from a rat 15 minutes after administration of an intravenous dose of 25mg/kg GX-071. The compounds were extracted from an alkaline aqueous phase to a methylene chloride phase as ion pairs and derivatized with pentafluorobenzyl-bromide. The levels of GX-071 and GX-071M in the blood of a rat after a single 150mg/kg oral dose of GX-071 again indicated that GX-071 was extensively metabolized to GX-071M. The percent reproducibility of the internal standard of the procedure was 4.7 and 2.8 at 100 parts per million and 17 and 21 at 400 parts per billion for GX-071 and GX-071M, respectively. The authors conclude that GX-071 undergoes significant hepatic metabolism on a first time pass prior to entry into the systemic circulation.

Absorption, Distribution and Excretion · 3 Einträge

The tissue distribution and elimination of sulfluramid were studied in rats. Male Sprague-Dawley-rats were administered 75mg/kg sulfluramid in their diet for 56 days before being switched to the control diet for 35 days. Selected rats were killed on days seven, 14, 28, or 56 of exposure or on days seven, ten, 17, 24, or 35 of the post exposure period and weighed. The blood, liver, spleen, kidneys, heart, lungs, brain, peritesticular fat, skeletal muscle, and testes were taken and analyzed for sulfluramid and its metabolite deethylsulfluramid. Sulfluramid caused no overt signs of toxicity. Terminal body weights were significantly decreased in the treated rats. The decreases were due to decreased body weight gain during the last 2 weeks of sulfluramid feeding. Sulfluramid could not be detected in the blood or any of the tissues. Deethylsulfluramid was detected in the blood and tissues at all times. Tissue deethylsulfluramid concentrations reached an apparent steady state early in the study whereas blood deethylsulfluramid concentrations decreased throughout exposure. At termination, deethylsulfluramid concentrations were highest in the fat, lung, and liver and lowest in the testes and muscle. The concentration of deethylsulfluramid in the blood and other tissues was intermediate to levels in the fat, lung, liver, testes, and muscle. Deethylsulfluramid was cleared from the blood and tissues during the post exposure period. The clearance half times in the blood, liver, spleen, kidney, heart, lung, brain, and fat were 10.8, 6.9, 5.5, 5.4, 4.5, 4.4, 2.6, and 1.1 days, respectively. Clearance half times could not be determined for the muscle and testes because the deethylsulfluramid concentrations in these tissues were too low. The authors conclude that sulfluramid is rapidly metabolized to deethylsulfluramid in rats, suggesting that the potential for bioaccumulation is low.

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Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
PubChem CID
77797
DTXSID
DTXSID1032646
ChEMBL
CHEMBL177726
ChEBI
CHEBI:81945
UNII
IPX089YR0A
EC Number
223-980-3
Nikkaji
J224.953G

0.00000043 [mmHg]

0.057 mPa (4.28X10-7 mm Hg) at 25 °C

Physical DescriptionColorless solid; [HSDB] Off-white powder; [MSDSonline]
Stability/Shelf LifeStable >90 days at 50 °C; to light >90 days in closed jar
Dissociation ConstantspKa = 9.50

Physikochemische Eigenschaften

Schmelzpunkt
75 · 75-85°C
Siedepunkt
120 °C · 120°C 0,5mm
Dichte
1.1561 · 1.1561
Dampfdruck
5.7 x · 5.7 x l0-5 Pa (25 °C)
Brechungsindex
1.5327 · 1.5327
storage temp.
-20 °C · -20°C Freezer
Löslichkeit
DMSO (Slightly), Methanol (Slightly)
pka
9.5 · 9.5 (very weak acid)
Wasserlöslichkeit
Insoluble (25 °C)
Henry's Law Constant
9.4 · 9.4×10-4 mol/(m3Pa) at 25℃, Abusallout et al. (2022)
InChIKey
CCEKAJIANROZEO-UHFFFAOYSA-N
CAS Datenbank
4151 · 4151-50-2(CAS DataBase Reference)
EPA chemische Informationen
Sulfluramid (4151-50-2)
FIFRA Requirements · 2 Einträge

The Agency has considered sulfluramid in light of the standard for registration and safety factors in FIFRA and FFDCA, as amended by FQPA. EPA has found that there are not likely to be any unreasonable adverse effects to the U.S. population, including infants and children in particular, or to other non-target organisms in the environment, from the use of products containing sulfluramid when currently required label instructions are followed. Based on all available information on sulfluramid, there are no new exposure concerns for currently registered products containing sulfluramid. The Agency has determined that no additional risk assessment, data, or mitigation measures are needed prior to the completion of the phase-out of the remaining product registrations. ... The Agency has determined that the standards for Registration Review have been met and that the registrations of currently registered products containing sulfluramid can be maintained until the end of the phase-out period.

New Active Ingredients ... includes chemicals not previously registered as pesticides, as well as pesticide active ingredients initially registered after November 1, 1984 and that currently have active product registrations. By law, these pesticides must meet new safety standards, such as those described in the Food Quality Protection Act of 1996 and, if new safety standards are met, will be reviewed again on a 15-year cycle. Sulfluramid is designated by EPA as a New Pesticide Active Ingredient. Active Ingredient Number: 128992; Type of Pesticide: conventional-insecticide; Use Site: greenhouse ornamental/non-food areas; Year: 1989.

Hazard Classes and CategoriesAcute Tox. 4 (98.5%)

Sicherheit und Schutzausrüstung

Fire Fighting ProceduresFor small fires, use chemical powder, CO2
Storage ConditionsDo not contaminate water, food or feed by storage ... Keep out of reach of children and animals. Store in original containers only. Store in a cool dry place and avoid excess heat. /FirstLine Termite Bait Station/
Cleanup Methods · 1 Eintrag

In case of spill, avoid contact, isolate area and keep out animals and unprotected persons. Confine spills. ... To confine spill: Cover to prevent dispersal. Place damaged package in a holding container. Identify contents. /FirstLine Termite Bait Station/

Disposal Methods · 3 Einträge

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

Wastes resulting from the use of this product may be disposed of on site or at an approved waste disposal facility. /FirstLine Termite Bait Station/

Container Disposal: Wrap FirstLine Tennite Bait Station and put in trash. Plastic bags: Completely empty bag. Then dispose of empty bag in a sanitary landfill or by incineration, or, if allowed by state and local authorities, by burning. If burned, stay out of smoke. /FirstLine Termite Bait Station/

Preventive Measures · 2 Einträge

Avoid contact with skin, eyes or clothing. Wash thoroughly with soap and water after handling. /FirstLine Termite Bait Station/

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

Personal Protective Equipment (PPE)Approved respirator. Chemical-resistant footwear plus socks. Chemical-resistant gloves. Long-sleeved shirt and long pants. Helmet.

Toxikologische Informationen

Body BurdenSulfluramid was not detected (<0.050 ng/mL) in 24 pooled serum samples from men, age 40 to 50 years, representing 1977 to 2006(1).
Ecotoxicity Values · 5 Einträge

LD50; Species: Colinus virginianus (Bobwhite quail) oral 473 mg/kg

LC50; Species: Anas platyrhynchos (Mallard duck) dietary 165 ppm

LC50; Species: Colinus virginianus (Bobwhite quail) dietary 460 ppm

LD50; Species: Colinus virginianus (Bobwhite quail) oral 473 mg/kg

For more Ecotoxicity Values (Complete) data for SULFLURAMID (8 total), please visit the HSDB record page.

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 7.9X10+5(SRC), determined from a structure estimation method(2), indicates that sulfluramid is expected to be immobile in soil(SRC). Volatilization of sulfluramid from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.4 atm-cu m/mole(SRC), using a fragment constant estimation method(3). However, adsorption to soil is expected to attenuate volatilization(SRC). Sulfluramid is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 4.28X10-7 mm Hg at 25 °C(4). As a class, perfluorinated organic compounds are resistant to microbial degradation(5). Similar to other perfluorinated sulfonamide derivatives, the potential exists for the conversion of the sulfonamide functional group to a sulfonic acid functional group via microbially-mediated hydrolysis(6).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 7.9X10+5(SRC), determined from a structure estimation method(2), indicates that sulfluramid is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 5.4 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 6.7 hours and 9.1 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 24 years if adsorption is considered(5). According to a classification scheme(6), an estimated BCF of 1.3X10+4(SRC), from an estimated log Kow of 6.8(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is very high(SRC). Hydrolysis is not expected to be an important environmental fate process since due to the presence of high-energy carbon-fluorine bonds(9).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), sulfluramid, which has a vapor pressure of 4.28X10-7 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase sulfluramid is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 1.8 days(SRC), calculated from its rate constant of 8.8X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase sulfluramid may be removed from the air by wet or dry deposition(SRC). The maximum absorption for sulfluramid is near 204 nm(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

Animal Concentrations · 2 Einträge

Concentrations of sulfluramid in 10 guillemot (Uria aalge) egg samples from each location. Sulfluramid was not detected (detection limit 1.1 ng/g wet weight) in 10 guillemot egg samples collected in 2003 from Sanday, Faroe Islands(1).[Table#6720]

Sulfluramid was detected in five narwhal (Monodon monoceros) and five beluga whales (Delphinapterus leucas) sampled from the Arctic at 0.5-6.9 and 0.1-11.7 ng/g wet weight, respectively(1).

Soil Adsorption/Mobility · 1 Eintrag

Using a structure estimation method based on molecular connectivity indices(1), the Koc of sulfluramid can be estimated to be 7.9X10+5(SRC). According to a classification scheme(2), this estimated Koc value suggests that sulfluramid is expected to be immobile in soil(SRC).

Atmospheric Concentrations · 3 Einträge

URBAN/SUBURBAN: Sulfluramid was detected in atmospheric samples from Barsbuttel, Germany at a maximum concentration of 1.4 pg/cu m, each sample was collected over a three to four day time span and the study was run April 2007 to June 2008(1).

RURAL/REMOTE: Perfluorinated chemicals have become widespread in the artic atmosphere(1). Sulfluramid was detected in atmospheric samples collected from onboard the Polarstern on a cruise from Bremerhaven, Germany to Capetown, Africa at concentrations of <0.3 to 2.2 pg/cu m; the cruise was run from Oct 13 to Nov 17, 2005(2).

INDOOR: Sulfluramid was detected in 40 indoor air samples from Oslo, Norway households at 0.30 to 95 pg/cu m(1). Sulfluramid was detected in 52 of 59 indoor air samples collected the winter of 2002 to 2003 from homes in Ottawa, Canada at concentrations of 5.94 to 646 pg/cu m(2).

Fish/Seafood Concentrations · 1 Eintrag

Sulfluramid was detected in five zooplankton, five clam (Mya truncata; Serripes groenlandica, five shrimp (Pandalus borealis; Hymenodora glacialis) and three Arctic cod (Boreogadus saida) samples at not detected to 0.65, 1.9 to 85.9, not detected to 44.8 and 9.6 to 144.6 ng/g, respectively(1). Sulfluramid was not detected in redfish (Sebastes mentella). Fish and shrimp samples were collected from Davis Strait, Nunavut, Canada, Oct of 2000 and 2001(1). Clams and zooplankton samples were collected from Frobisher Bay, Nunavut, Canada, May 2002(1).

Artificial Pollution SourcesSulfluramid's production may result in its release to the environment through various waste streams; its use as an insecticide(1) will result in its direct release to the environment(SRC).
Environmental Biodegradation · 1 Eintrag

As a class, perfluorinated organic compounds, such as sulfluramid, are resistant to microbial degradation(1). Similar to other perfluorinated sulfonamide derivatives, the potential exists for the conversion of the sulfonamide functional group to a sulfonic acid functional group via microbially-mediated hydrolysis(2). However, sulfonamides cannot be characterized as readily biodegradable(3).

Environmental Bioconcentration · 1 Eintrag

An estimated BCF of 1.3X10+4 was calculated in fish for sulfluramid(SRC), using an estimated log Kow of 6.8(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is very high(SRC), provided the compound is not metabolized by the organism(SRC).

Volatilization from Water/Soil · 1 Eintrag

The Henry's Law constant for sulfluramid is estimated as 5.4 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that sulfluramid is expected to volatilize rapidly from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 6.7 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 9.1 days(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The volatilization half-life from a model pond is about 24 years when adsorption is considered(3). Sulfluramid's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Sulfluramid is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 4.28X10-7 mm Hg(4).

Non-Human Toxicity Excerpts · 5 Einträge

/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ Sulfluramid, suspended in 1% CMC/0.1% Tween 80, was administered by gavage to three groups of 22 timed-pregnant, "litter-experienced" New Zealand White rabbits from gestation days 19-28 at levels of 0.3, 1.0 and 3.0 mg/kg/day. The F0 females were allowed to deliver naturally and rear their bunnies to PND (postnatal day) 42. Selected F1 bunnies were evaluated for developmental landmarks, and a longitudinal quantitative assessment of spermatogenesis was performed on semen from all selected F1 males. The number of bunnies stillborn or found dead on PND 0 was increased, and the viability on PND 1 was decreased in the 3.0 mg/kg/day group. In addition, postnatal viability indices in all treated groups were decreased throughout the pre-weaning period (PND 4-42). No treatment-related effects were noted on the age at which balanopreputial separation or vaginal patency occurred. The numbers of sperm/ejaculate, percentages of motile sperm, numbers of motile sperm/ejaculate and percentages of sperm with normal morphology were apparently unaffected by treatment during the 4-week longitudinal assessment of spermatogenesis. No adverse effects were apparent on mean testicular and epididymal sperm numbers, and no treatment-related histopathological findings were noted in the reproductive organs at any dose level. Although significant neonatal toxicity (mortality) was noted in all treatment groups, no treatment-related effects were noted on sexual maturation or testicular function of the F1 generation in this study.

/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ Administration of sulfluramid (96.6% linear and 3.4% branched isomeric mixture) at dose levels of 0.8, 3.3, and 13.3 mg/kg/day from day 6 to day 15 of gestation reduced the mean maternal body weight and mean body weight gain in the 3.3 and 13.3 mg/kg/day dose groups, and reduced food consumption in the 13.3 mg/kg/day dose group. Treatment-related maternal toxicity effects, flaccid body tone and piloerection, were noted in the 13.3 mg/kg/day group. A dose-related trend of increased incomplete ossification of the 3rd and 4th sternebrae and skull, and an enlarged fontanelle were noted in the high-dose group. The reduced fetal weights and increased incidence of cleft palate (3.5% of fetuses and 16.7% of litters in this study versus 0.02% fetuses in the fetal historical control) in the 13.3 mg/kg/day are other developmental toxicity effects. The maternal toxicity NOAEL is determined to be 0.8 mg/kg/day, and the maternal toxicity LOAEL is 3.3 mg/kg/day based on reduced mean maternal body weight, mean body weight gain and the reduced food consumption. The developmental toxicity NOAEL is 3.3 mg/kg/day and the developmental toxicity LOAEL is 13.3 mg/kg/day based on reduced fetal weights and increased incidence of cleft palate, incomplete ossification of the 3rd and 4th sternebrae and skull and an enlarged fontanelle.

/GENOTOXICITY/ Under the conditions of the assay, four doses of sulfluramid (0.5, 0.75, 1.0, and 1.25 ug/mL) did not induce an appreciable increase in the net nuclear grain counts of treated rat hepatocytes. Cytotoxicity was clearly demonstrated at concentrations > or = 1.5 ug/mL. It is concluded, that sulfluramid is not genotoxic in the primary rat hepatocyte unscheduled DNA synthesis (UDS) assay.

Regulatorische Informationen

TSCA Requirements · 1 Eintrag

Certain perfluoroalkyl sulfonates. (a) Chemical substances and significant new uses subject to reporting. (1) The chemical substances listed /including 1-Octanesulfonamide, N-ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluoro-/ ... are subject to reporting under this section for the significant new uses described in paragraph (a)(2) of this section. ... (2) The significant new uses are: ... (ii) Any manufacture or import for any use ... except as noted in paragraph (a)(3) of this section. ... (a)(3) Manufacture or import ... for the following specific uses shall not be considered as a significant new use subject to reporting under this section: (i) Use as an anti-erosion additive in fire-resistant phosphate ester aviation hydraulic fluids. (ii) Use as a component of a photoresist substance, including a photo acid generator or surfactant, or as a component of an anti-reflective coating, used in a photomicrolithography process to produce semiconductors or similar components of electronic or other miniaturized devices. (iii) Use in coating for surface tension, static discharge, and adhesion control for analog and digital imaging films, papers, and printing plates, or as a surfactant in mixtures used to process imaging films. (iv) Use as an intermediate only to produce other chemical substances to be used solely for the uses listed in paragraph (a)(3)(i), (ii), or (iii) of this section.

FIFRA Requirements · 2 Einträge

The Agency has considered sulfluramid in light of the standard for registration and safety factors in FIFRA and FFDCA, as amended by FQPA. EPA has found that there are not likely to be any unreasonable adverse effects to the U.S. population, including infants and children in particular, or to other non-target organisms in the environment, from the use of products containing sulfluramid when currently required label instructions are followed. Based on all available information on sulfluramid, there are no new exposure concerns for currently registered products containing sulfluramid. The Agency has determined that no additional risk assessment, data, or mitigation measures are needed prior to the completion of the phase-out of the remaining product registrations. ... The Agency has determined that the standards for Registration Review have been met and that the registrations of currently registered products containing sulfluramid can be maintained until the end of the phase-out period.

New Active Ingredients ... includes chemicals not previously registered as pesticides, as well as pesticide active ingredients initially registered after November 1, 1984 and that currently have active product registrations. By law, these pesticides must meet new safety standards, such as those described in the Food Quality Protection Act of 1996 and, if new safety standards are met, will be reviewed again on a 15-year cycle. Sulfluramid is designated by EPA as a New Pesticide Active Ingredient. Active Ingredient Number: 128992; Type of Pesticide: conventional-insecticide; Use Site: greenhouse ornamental/non-food areas; Year: 1989.

Sicherheitsdaten

wgk
3
tsca
TSCA listed
ridadr
UN 3077 9 / PGIII
RTECS-Nr.
RG9701300
risk_code
21-22-51/53
Toxizität
LD50 oral in rat: 543mg/kg
hazard_code
Xi,N,Xn
hazard_note
Irritant
safety_code
36/37-61
Giftige Stoffe Daten
4151-50-2(Hazardous Substances Data)

The metabolism and disposition of the polyfluorinated insecticide N-ethylperfluorooctane-sulfonamide (sulfluramid) were studied in rats. Male and female Sprague-Dawley-rats were administered 50 mg/kg carbon-14 (C-14) labeled sulfluramid orally in polyethylene-glycol (PEG). Feces, urine, and expired air samples were collected at various times for up to 72 hours and assayed for C-14 activity. The rats were killed after 72 hours to determine the tissue distribution of sulfluramid. Male Sprague-Dawley-rats some with cannulated carotid arteries were administered an oral bolus of sulfluramid in PEG or corn-oil. Blood samples were collected for up to 96 hours and analyzed for sulfluramid and perfluorooctane-sulfonamide (DESFA), a major sulfluramid metabolite. Approximately 80% of the dose was recovered after 72 hours. The major elimination routes were expired air and feces, which accounted for 55 and 25% of the dose, respectively. Approximately 7.9 and 8.9% of the dose was excreted in the urine by male and female rats, respectively. The difference was statistically significant. The highest tissue concentrations of sulfluramid derived radioactivity in male rats occurred in the liver, kidney, and adrenals. The highest tissue C-14 concentrations in females occurred in the liver, kidney, adrenals, and gonads. The concentrations of C-14 label in the kidneys, gonads, and adrenals of female rats were significantly higher than in males. Sulfluramid was absorbed slowly from the gastrointestinal tract. The times to maximum blood concentration in rats given sulfluramid in PEG or corn-oil were 4.1 and 10.1 hours, respectively. Once absorbed, sulfluramid was rapidly metabolized to DESFA. The mean halflives for clearing sulfluramid from the blood of rats given the compound in PEG and corn-oil were 16.2 and 20.4 hours, respectively. The corresponding mean clearance times for DESFA were 102.9 and 106.7 hours. The authors conclude that sulfluramid appears to be absorbed slowly and incompletely in rats after oral administration. It is rapidly converted to DESFA once it is absorbed. Corn-oil slightly increases sulfluramid absorption when it is used as the vehicle relative to PEG.

Pharmacokinetic properties and tissue residues of the insecticide sulfluramid (I) and its major metabolite desethylsulfluramid (II) were determined in healthy sheep after bolus intravenous (IV) administration (5 and 15 mg/kg; n = 10) and bolus intraruminal (IR) administration (100 and 400 mg/kg; n = 12) of I. Depression, lethargy, and dyspnea were noted for 4hr after the higher IV dose, but not after the other IV or IR doses. The time courses of the mean blood concentrations of I and II were best described by a two-compartment open model with rapid distribution and slow elimination phases. The blood-to-plasma concentration ratios for I and II were 1.43 (+/- 0.50) and 26.7 (+/- 9.41), respectively, suggesting binding of II to red blood cells. The T1/2beta values for I and II for the higher IV dose of I were 15.3 (+/- 4.68) hr and 63.4 (+/- 4.75) hr and for the higher IR dose of I, 31.5 (+/- 5.41) hr and 74.9 (+/- 7.49) hr, respectively. Bioavailability was 28.6 (+/- 2.96)% for the lower IR dose and 19.5 (+/- 0.99)% for the higher IR dose. Cmax values for II were higher in female than male sheep after IR administration of I. Only II was found in tissue samples, with the highest concentration being in liver (9.4 (+/- 5.2) ug/g).

Verwendung und Herstellung

Uses · 6 Einträge

Used as insecticide for control of household ants and cockroaches; [HSDB]

For sulfluramid (USEPA/OPP Pesticide Code: 128992) ACTIVE products with label matches. /SRP: Registered for use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Sulfluramid is currently registered only for use as a termiticide in pre-filled bait stations (including perforated tubes and stakes) that are placed around building perimeters (residential, food establishments, and other institutions).

Used for household control of Formicidae /ants/ and Blattellidae /cockroaches/.

Insecticide

non-polymer PFAS -> Manufacture of Metal Products -> Treatment and coating of metal

U.S. ProductionProduction volumes for non-confidential chemicals reported under the Inventory Update Rule.[Table#6723]
Formulations/Preparations · 5 Einträge

Solid, pellets.

Principal tradename: Finitron (Griffin).

Technical is 98.0%.

Firstline Termite Bait Station (FMC Corp. Agricultural Products Group) Sulfluramid 0.01%.

For more Formulations/Preparations (Complete) data for SULFLURAMID (10 total), please visit the HSDB record page.

Household ProductsInformation on 3 consumer products that contain N-Ethyl perfluorooctane sulfonamide in the following categories is provided:
Use Classification · 2 Einträge

PFAS -> PFalkylsulfonamides (FASA)

PFAS (per- and polyfluoroalkyl substances) -> OECD Category

General Manufacturing Information · 3 Einträge

1-Octanesulfonamide, N-ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluoro-: ACTIVE

In 2001, the Agency completed human health and ecological risk assessments to assess new proposed uses for products containing sulfluramid. Because of the potential toxicity concern resulting from bioaccumulation of the Perfluorooctane Sulfonate (PFOS) degradate in animals, as well as evidence of developmental and reproductive effects in toxicity studies, EPA negotiated in 2001 with all U.S. registrants a phase-out of products containing sulfluramid, with all registrations set to expire by December 31, 2016. Additionally, DuPont, the sole technical registrant, agreed to discontinue producing any new sulfluramid manufacturing-use product and the acquisition or importation of any additional sulfluramid into the U.S. At the beginning of the registration review process for sulfluramid in 2007, the technical registrant informed the Agency that they exhausted their sulfluramid supply; all remaining sulfluramid stocks were sold to the end-use registrants. The Agency issued the product cancellation order for the last remaining sulfluramid manufacturing-use product registration on May 16, 2008 (73 FR 28465-28469). Based on the remaining supply of sulfluramid stocks, the Agency renegotiated the phase-out terms with the end-use registrants so that all product registrations are to expire by December 31, 2012. End-use registrants will be permitted to sell the remaining stocks for one additional year after the expiration of the product registrations. Distributors and retailers are permitted to sell existing stocks of end-use sulfluramid products until all stocks in the supply chain are exhausted. Currently, there are seven remaining registered end-use products that contain sulfluramid as an active ingredient.

The WHO Recommended Classification of Pesticides by Hazard identifies sulfluramid (technical grade) as Class II: moderately hazardous; Main Use: insecticide.

Anwendungen

VerwendenSulfluramid is an insecticide.

Vor- und nachgelagerte Produkte

Nachgelagerte Produkte

N-ethyl perfluorooctylsulfonylaminoacetateN-Ethyl-N-[(heptadecafluoroctyl)sulfonyl]glycinN-Allyl-N-ethylheptadecafluoroctansulfonamid

Anbieter82 Anbieter

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Ergänzende Hinweise

DefinitionChEBI: A sulfonamide obtained by the formal condensation of perfluorooctane-1-sulfonic acid with ethylamine.

/GENOTOXICITY/ Under the conditions of this assay, OX-071 /sulfluramid/ was found to be negative for induction of sister chromatid exchange in Chinese Hamster ovary cells, both with and without metabolic activation, at concentrations up to 1000 ug/mL. However, this top concentration did not result in at least a 50% reduction in the second mitosis.

For more Non-Human Toxicity Excerpts (Complete) data for SULFLURAMID (6 total), please visit the HSDB record page.