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Volcano

Volcano structure

Volcano 

structure
  • CAS No:

    4151-50-2

  • Formula:

    C10H6F17NO2S

  • Chemical Name:

    Volcano

  • Synonyms:

    1-Octanesulfonamide,N-ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluoro-;N-Ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluoro-1-octanesulfonamide;GX 071;AI 3-29757;Sulfluramid;FiniTron;N-Ethylperfluorooctanesulfonamide;Alstar;Alstar (pesticide);N-Ethylperfluorooctylsulfonamide;Mirex S;Volcano;Volcano (insecticide);FX 12;N-Ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonamide;Sulfluramide

  • Categories:

    Agrochemicals  >  Pesticide Intermediates

Description

Tan Powder


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

Volcano Basic Attributes

527.19

527.20

223-980-3

IPX089YR0A

DTXSID1032646

Colorless crystals|Brown crystals

2935009018

Characteristics

54.6

6.80 (un-ionized)

Tan powder

1.7±0.1 g/cm3

96 °C

196 °C

102.9±30.1 °C

1.321

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

-20°C Freezer

5.7 x l0 -5 Pa (25 °C)

LD50 oral in rat: 543mg/kg

Very weak acid

Henry's Law constant = 5.37 atm-cu m/mol at 25 °C (est)

pKa = 9.50

178.42 Ų [M-H]-

Hydroxyl radical reaction rate constant = 8.85X10-12 cu cm/molecule-sec at 25 °C (est)

Safety Information

UN 3077 9 / PGIII

3

21-22-51/53

36/37-61

RG9701300

Xi,N,Xn

Irritant

Stable >90 days at 50 deg C; to light >90 days in closed jar

P273-P280

H302 + H312-H411

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/

|Warning|H302+H312 (100%): Harmful if swallowed or in contact with skin [Warning Acute toxicity, oral; acute toxicity, dermal]|P264, P270, P273, P280, P301+P312, P302+P352, P312, P322, P330, P363, P391, and P501|Aggregated GHS information provided by 127 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Approved respirator. Chemical-resistant footwear plus socks. Chemical-resistant gloves. Long-sleeved shirt and long pants. Helmet.

For small fires, use chemical powder, CO2

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/

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.

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).

Sulfluramid was detected in 41 dust samples from Norwegian households at 0.26 to 33 ng/g(1). Sulfluramid was not detected in 66 dust samples from households in Ottawa, Canada, samples were collected the winter of 2002 to 2003(2).

Toxicity

LD50 Rat oral 543 mg/kg|LD50 Rabbit dermal > 2000 mg/kg|LD50 Rat (male) oral 607 mg/kg|LD50 Rat (female) oral 507 mg/kg|LD50 Rat dermal 1250mg/kg

Sulfluramid'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).

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).

The rate constant for the vapor-phase reaction of sulfluramid with photochemically-produced hydroxyl radicals has been estimated as 8.8X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 1.8 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Hydrolysis is not expected to be an important environmental fate process since due to the presence of high-energy carbon-fluorine bonds(2). The maximum absorption for sulfluramid is near 204 nm(3) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

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).

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).

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).

SURFACE WATER: Surface water samples taken from US streams in the Great Lakes basin tested positive for sulfluramid in 6% of 16 samples taken 1994 to 2000 at a concentration of 0.0003 ug/L(1).|SEAWATER: Perfluoroalkyl acids are ubiquitous contaminants of marine as well as freshwater and terrestrial, environments. The slow and long-range transport from source areas in the Northern Hemisphere is suggested as one of the major pathways contributing to perfluoroalkyl acid conamination in remote marine environments(1). /Perfluoroalkylacids/

Occupational exposure to sulfluramid may occur through inhalation and dermal contact with this compound at workplaces where sulfluramid is produced or used. Monitoring data indicate that the general population may be exposed to sulfluramid via inhalation of ambient air and ingestion of food. (SRC)

Sulfluramid was not detected (<0.050 ng/mL) in 24 pooled serum samples from men, age 40 to 50 years, representing 1977 to 2006(1).

Drug Information

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.|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).

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.

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

N-ethyl(perfluorooctane)sulfonamide

Volcano Use and Manufacturing

Uses

This product is an important intermediate for the synthesis of perfluorinated anionic surfactants and perfluorinated fabric finishing agents. At the same time, it can be used as an insecticide by itself to control termites, ants, cockroaches and other pests. Used as an emulsifier, wetting agent, and as an organic fluoride insecticide; highly effective, broad-spectrum, antibacterial, suitable for various bacterial infections

Production

Production volumes for non-confidential chemicals reported under the Inventory Update Rule.[Table#6734]

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.

1-Octanesulfonamide, N-ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluoro-: ACTIVE|S - indicates a substance that is identified in a final Significant New Use Rule.|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.

Product analysis by gas liquid chromatography.

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

Computed Properties

Molecular Weight:527.20
XLogP3:5.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:20
Rotatable Bond Count:9
Exact Mass:526.9847784
Monoisotopic Mass:526.9847784
Topological Polar Surface Area:54.6
Heavy Atom Count:31
Complexity:763
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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