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3-Iod-2-propinylbutylcarbamat
IPBC · 3-IODO-2-PROPYNYL BUTYLCARBAMATE · IODOCARB · 3-IODO-2-PROPYNYL N-BUTYLCARBAMATE · lodopropynyl butylcarbamate · IBP · Iodopropynyl · troysanpolyphaseanti-mildew
Identifikatoren & physikalische Daten
| CAS No. | 55406-53-6 |
|---|---|
| Summenformel | C8H12INO2 |
| Durchschnittliche Molmasse | 281,09 g/mol |
| Monoisotopische Masse | 280,99127662 g/mol |
| SMILES | CCCCNC(=O)OCC#CI |
| InChIKey | WYVVKGNFXHOCQV-UHFFFAOYSA-N |
| PubChem CID | 62097 |
| ChEMBL | CHEMBL1893913 |
| ChEBI | CHEBI:83279 |
| EC No. | 259-627-5 |
| DTXSID | DTXSID0028038 |
| Lokaler Name | 3-Iod-2-propinylbutylcarbamat |
Chemische & physikalische Eigenschaften
| XLogP | 2,1 |
|---|---|
| Polarare Oberfläche (TPSA) | 38,3 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 5 |
| Schwere Atome | 12 |
| Formalladung | 0 |
| Komplexität | 192 |
| Stoffklassen | Other Uses -> Biocides/Disinfectants |
| Kosmetika | Cosmetic ingredients (Iodopropynyl Butylcarbamate) -> CIR (Cosmetic Ingredient Review)Cosmetic ingredients (Iodopropynyl Butylcarbamate (IPBC)) -> CIR (Cosmetic Ingredient Review)Preservative |
| Pestizide | Biocide |
| LogP (Verteilungskoeffizient) | log Kow = 2.4 /Estimated/ |
| Geruch | Sharp pungent odor |
| Dichte | 1.575 g/mL1.575 @25 °C1.606±0.06 g/cm3(Predicted) |
| Color/Form | Off-white, dull color powderWhite, crystalline powder |
| Löslichkeit | In water, 156 mg/L at 20 °Csoluble in Methanol168mg/L at 20℃ |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Schmelzpunkt | 66 °C64-68 °C(lit.) |
| Dampfdruck | 0.0000525 [mmHg]5.25X10-5 mm Hg at 30 °C0.0000525 [mm Hg] @30 °C0.005Pa at 25℃ |
| Food Contact Substances | FCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR |
| Siedepunkt | 321.8±25.0 °C(Predicted) |
| Lagerbedingungen | Keep in dark place,Sealed in dry,2-8°C |
| Aggregatzustand | Solid |
| pKa (Säurekonstante) | 12.03±0.46(Predicted) |
| Farbe | White to Almost white |
| Merck | 14,5069 |
| Henry-Konstante | 8.2×101 mol/(m3Pa) at 25℃, HSDB (2015) |
| Stabilität | Stable. Incompatible with strong oxidizing agents. |
| Hauptanwendungen | cleaning productscosmeticsfood and beveragespersonal care |
| Kosmetik-Inhaltsstoffe Funktionen | PRESERVATIVE |
| InChI | 1S/C8H12INO2/c1-2-3-6-10-8(11)12-7-4-5-9/h2-3,6-7H2,1H3,(H,10,11) |
| InChIKey | WYVVKGNFXHOCQV-UHFFFAOYSA-N |
| SMILES | CCCCNC(=O)OCC#CI |
| LogP (Verteilungskoeffizient) | 2.81 at 25℃ |
| CAS Datenbank | 55406-53-6(CAS DataBase Reference) |
| EPA chemische Informationen | 3-Iodo-2-propynyl butylcarbamate (55406-53-6) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH302: Harmful if swallowed [Warning Acute toxicity, oral]P260, P261, P264, P264+P265, P270, P271, P272, P273, P280, P301+P317, P302+P352, P304+P340, P305+P354+P338, P316, P317, P319, P321, P330, P333+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)This chemical does not meet GHS hazard criteria for 0.3% (6 of 1729) of reports.H302+H332 (25.6%): Harmful if swallowed or if inhaled [Warning Acute toxicity, oralacute toxicity, inhalation] |
|---|---|
| Regulatorische Informationen | Chemical: Carbamic acid, butyl-, 3-iodo-2-propynyl esterCarbamic acid, N-butyl-, 3-iodo-2-propyn-1-yl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Carbamic acid, N-butyl-, 3-iodo-2-propyn-1-yl ester are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 01-09-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/23059Iodocarb: HSNO Approval: HSR002733 Approved with controls |
| Weitere Sicherheitsinformationen | Evaluation - Carbamic acid, butyl-, 3-iodo-2-propynyl ester (IPBC) |
| DOT-Kennzeichnung | Class 9 |
| Brandgefahren | Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: |
| Gesundheitsgefahren | Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: |
| Gefahrenübersicht | Positive patch tests reported in worker in a paint factory and in patients sensitized by cosmeticsAnimals in high-dose feeding studies have cardiomegaly and injury to the kidneys and liver[HSDB] Danger of skin sensitization[MAK] Causes allergic contact dermatitis in cosmetics, sanitary wipes, and metalworking fluids[Kanerva, p. 1804] May cause irritation[MSDSonline] |
| FDA-Anforderungen | 3-Iodo-2-propynyl-N-butyl carbamate is an indirect food additive for use only as a component of adhesives. For use only as an antifungal preservative. |
| Reaktive Gruppe | Carbamates |
| Special Reports | USEPA/Office of Pesticide ProgramsReregistration Eligibility Decision Document - 3-Iodo-2-propynyl butylcarbamate( IPBC). EPA 738-R-97-003 March 1997. Available from the Database Query page at http://cfpub.epa.gov/oppref/rereg/status .cfm?show=rereg as of January 31, 2005. The RED summarizes the risk assessment conclusions and outlines any risk reduction measures necessary for the pesticide to continue to be registered in the U.S. |
| FIFRA-Anforderungen | As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. 3-Iodo-2-propynyl butylcarbamate is found on List B. Case No: 2725Pesticide type: fungicideCase Status: RED Approved 3/97OPP has made a decision that some/all uses of the pesticide are eligible for reregistration, as reflected in a Reregistration Eligibility Decision (RED) document .Active ingredient (AI): 3-iodo-2-propynyl butylcarbamateData Call-in (DCI) Date(s): 4/30/91, 5/29/97AI Status: OPP has completed a Reregistration Eligibility Decision (RED) for the case/AI.Based on the reviews of the generic data for the active ingredient IPBC, the Agency has sufficient information on the health effects of IPBC, and on its potential for causing adverse effects in fish and wildlife and the environment, for all uses except industrial wood protection treatments to milled forest products, textile uses, HVAC uses, and certain non-industrial 34 applications to wood. The Agency has determined that IPBC products, labeled and used as specified in this Reregistration Eligibility Decision, will not pose unreasonable risks or adverse effects to humans or the environment, and that products containing IPBC, with the exceptions noted below, are eligible for reregistration. ... Eligibility decisions on products containing the industrial treatments to milled forest products use, HVAC use, textile uses, and non-industrial wood treatments using methods other than brush, roller and airless or compressed air sprayer, will be made after the exposure data specified in section V.A.1 are received and evaluated. Products containing these uses are not eligible for reregistration at this time. The Agency has determined that all other uses, except those specifically noted above, are eligible for reregistration. |
| Reactivity Profile | 3-IODO-2-PROPYNYL BUTYLCARBAMATE is a carbamate ester. Carbamates are chemically similar to, but more reactive than amides. Like amides they form polymers such as polyurethane resins. Carbamates are incompatible with strong acids and bases, and especially incompatible with strong reducing agents such as hydrides. Flammable gaseous hydrogen is produced by the combination of active metals or nitrides with carbamates. Strongly oxidizing acids, peroxides, and hydroperoxides are incompatible with carbamates. |
| Air and Water Reactions | No rapid reaction with air. No rapid reaction with water. |
| Brandbekämpfung | Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: |
| Erste Hilfe | Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: |
| Expositionsschutz und Persönliche Schutzausrüstung | 0.05 [mg/m3], (can also occur as vapor and aerosol)[German Research Foundation (DFG)] |
| Freisetung ohne Brand | Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: |
| Entsorgungsverfahren | SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure 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 qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations. |
| Isolation and Evacuation | Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: |
| Protective Action Criteria (PAC) | 0.116 [mg/m3]49 [mg/m3]290 [mg/m3] |
| Personal Protective Equipment (PPE) | Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: |
| Treatment | If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally. |
| Gesundheitliche Auswirkungen | Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Chronically high (>10 years) exposure leads to neuropsychological consequences including disturbances in perception and visuo-motor processing (A15321). |
| Ökotoxizitätswerte | LC50 Anas platyrhyncos (Mallard duck, 10 days old) dietary >5620 ppm/8 daysLD50 Colinus virginianus (Northern bobwhite, 21 weeks old) oral 970 mg/kg/21 daysLD50 Colinus virginianus (Northern bobwhite, 23 weeks old) oral 749 mg/kg/14 daysLC50 Colinus virginianus (Northern bobwhite, 10 days old) dietary >5620 ppm/8 daysFor more Ecotoxicity Values (Complete) data for 3-IODO-2-PROPYNYL BUTYLCARBAMATE (15 total), please visit the HSDB record page. |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), Koc values ranging from 62-310(2) indicate that 3-iodo-2-propynyl butylcarbamate is expected to have high to moderate mobility in soil(SRC). Volatilization of 3-iodo-2-propynyl butylcarbamate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.2X10-7 atm-cu m/mole(SRC) based upon its vapor pressure, 5.25X10-5 mm Hg(2), and water solubility, 156 mg/L(2). 3-Iodo-2-propynyl butylcarbamate is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(2). 3-Iodo-2-propynyl butylcarbamate is expected to biodegrade quickly in soil based on a half-life of 2.13 hours(2). A hydrolysis half-life of 0.947 days at pH 9(2) indicates that hydrolysis will also be an important fate process in basic soils. 3-Iodo-2-propynyl butylcarbamate was not detected in soil samples from a spill area several days following the incident(2). The concentration of 3-iodo-2-propynyl butylcarbamate that was spilled ranged from 700-2000 mg/L.AQUATIC FATE: Based on a classification scheme(1), Koc values ranging from 62-310(2), indicate that 3-iodo-2-propynyl butylcarbamate is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.2X10-7 atm-cu m/mole(SRC), derived from its vapor pressure, 5.25X10-5 mm Hg(2), and water solubility, 156 mg/L(2). According to a classification scheme(4), an estimated BCF of 36(SRC), from a water solubility of 156 mg/L(2) and a regression-derived equation(5), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). This substance is expected to biodegrade quickly in water based on a biodegradation half-life 1.5 hours in a static, anaerobic sediment water system(2). Hydrolysis may be an important fate process under basic conditions based on a half life of 0.947 days at pH 9(2). The half-life of 3-iodo-2-propynyl butylcarbamate in an anaerobic, non-sterile, static, sediment-water system was 1.5 hours compared to 13.3 hours in a sterile, static, sediment-water system(2).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 3-iodo-2-propynyl butyl carbamate, which has a vapor pressure of 5.25X10-5 mm Hg at 30 °C(2), is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase 3-iodo-2-propynyl butylcarbamate 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 1.5 hours(SRC), calculated from its rate constant of 2.6X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase 3-iodo-2-propynyl butylcarbamate may be removed from the air by wet and dry deposition(SRC). |
| Unerwünschte Wirkungen | Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation. |
| Expositionspfade | Inhalation (L793)oral (L793)dermal (L793) |
| Toxizitätsübersicht | On the basis of the data presented in this report, the CIR Expert Panel concludes that Iodopropynyl Butylcarbamate (IPBC) is safe as a cosmetic ingredient at concentrations 𕟨.1%. IPBC should not be used in products intended to be aerosolized.Safe for use in cosmetics, with qualifications3-Iodo-2-propynyl butyl carbamate is a cholinesterase or acetylcholinesterase (AChE) inhibitor. Carbamates form unstable complexes with chlolinesterases by carbamoylation of the active sites of the enzymes. This inhibition is reversible. A cholinesterase inhibitor suppresses the action of acetylcholine esterase. Because of its essential function, chemicals that interfere with the action of acetylcholine esterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses. Headache, salivation, nausea, vomiting, abdominal pain and diarrhea are often prominent at higher levels of exposure. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop. |
| Ökotoxizitätsauszüge | /AQUATIC SPECIES/ The antisapstain chemicals DDAC and IPBC were tested for acute toxicity with juvenile rainbow trout. The 96-hr LC50 estimates were 537 ug DDAC and 67 ug IPBC/L. The two chemicals were also tested as a mixture (10:1) and as the commercial formulation NP-1. The 96-hr LC50 for NP-1 was 581 ug DDAC + IPBC/L and was 494 ug DDAC + IPBC/L for the 10:1 mixture. The two chemicals exhibited mildly antagonistic behavior when present in the mixture or formulation. |
| Signs and Symptoms | As with organophosphates, the signs and symptoms are based on excessive cholinergic stimulation. Unlike organophosphate poisoning, carbamate poisonings tend to be of shorter duration because the inhibition of nervous tissue acetylcholinesterase is reversible, and carbamates are more rapidly metabolized. Muscle weakness, dizziness, sweating and slight body discomfort are commonly reported early symptoms. Headache, salivation, nausea, vomiting, abdominal pain and diarrhea are often prominent at higher levels of exposure. Contraction of the pupils with blurred vision, incoordination, muscle twitching and slurred speech have been reported. (L795) |
| Soil Adsorption/Mobility | Reported Koc values for 3-iodo-2-propynyl butylcarbamate range from 62-310(1). According to a classification scheme(2), this Koc range suggests that 3-iodo-2-propynyl butylcarbamate is expected to have high to moderate mobility in soil. |
| Human Toxicity Excerpts | /HUMAN EXPOSURE STUDIES/ ...From 1996 to 1999, a total of 3168 persons (2093 women and 1075 men) were patch tested with IPBC, and 7 cases were found to be positive. In 2 cases, sensitization could be attributed to cosmetics, and in a further 2 cases cosmetics were the most likely cause of sensitization./CASE REPORTS/ ... A 34-year-old female production worker at a paint factory developed dermatitis on exposed skin areas. Patch testing showed a positive reaction to IPBC 0.01% in petrolatum./CASE REPORTS/ A 63-year old man developed severe perianal and palmar contact dermatitis caused by sensitization to iodopropynyl butylcarbamate in moist sanitary wipes./EPIDEMIOLOGY STUDIES/ ... An analysis was made of data filed by 26 centers of dermatology on patch tests performed with one or two concentrations of IPBC (0.1%, 0.2%, 0.3% or 0.5%) in 8106 unselected patients. ...IPBC 0.1%, 0.2%, 0.3% and 0.5% yielded 0.5%, 0.8%, 1.3% and 1.7% positive reactions, but this increase was accompanied by an even greater increase in doubtful and irritant reactions. These figures and the other criteria examined suggested the range of suitable test concentrations of IPBC to lie between 0.2% and 0.3%. A detailed analysis of MOAHLFA indices and of associations between reactions to IPBC and reactions to other allergens and to SLS showed that most of the positive reactions to IPBC 0.2% can be assumed to be allergic ones and that with IPBC 0.2% fewer false-positive reactions can be expected than with IPBC 0.3%./BIOMONITORING/ The preservative iodopropynyl butylcarbamate (IPBC) (0.1% in petrolatum) was tested in 4883 consecutive patients for 18 months between January 1998 and June 1999. ...According to readings at D3, 0.3% were allergic to IPBC, with 14 + and 2 + + reactions. Doubtful or irritant reactions occurred twice as frequently. Patients exposed for 24 hr (n=1814) reacted less frequently (0.1%) than the remaining patients exposed for 48 hr (0.5%). ...More than 80% of the positive reactions displayed a crescendo or plateau time pattern. Furthermore, 18 of 43 doubtful reactions appeared as late as D3 (thus, these could be false negative), whereas the majority of doubtful reactions occurred earlier and displayed a decrescendo pattern (corresponding to a typical irritant pattern). |
| Artificial Pollution Sources | 3-Iodo-2-propynyl butyl carbamate's production may result in its release to the environment through various waste streamsit's use as a fungicide in paint, adhesives, emulsion, paper coatings, metal cutting fluids, oil recovery drilling fluids, plastics, textiles, inks, canvas, air conditioner and furnace filters, and wood products(1) will result in its direct release to the environment(SRC). |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | 3077 |
| Zollcode | 29241990 |
| RTECS-Nr. | EZ0950000 |
| R-Sätze (R) | 50/53-50 |
| Toxizität | LD50 orally in rats: 1580 mg/kgdermally in rabbit: >2000 mg/kgLC50 (96 hr) in bluegill sunfish, rainbow trout, bobwhite quail: 1.12, 0.31, >7683 ppmLC50 (8 day) in mallard duck: >7182 ppm (Hansen) |
| Gefahrensymbole | N |
| Sicherheitshinweise (S) | 60-61-29 |
| Gefahrenklasse | 9Acute Tox. 3 InhalationAcute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Eye Dam. 1Skin Sens. 1STOT RE 1 |
| Verpackungsgruppe | III |
| Lagerklasse | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| Gefahrstoffdaten | 55406-53-6(Hazardous Substances Data) |
Anwendungen & Verwendung
Beschreibung
Iodopropynyl butylcarbamate is a preservative that has been used as an industrial fungicide since the 1970s and more recently has been combined with formaldehydereleasing agents for use in cosmetics. The North American Contact Dermatitis Group patch tested with 0.1%iodopropynyl butylcarbamate in petrolatum and found 0.2% of their patch test clinic patients had positive reactions to this chemical. Most cosmetic applications appear to require less than 0.012% of this preservative.
Verwenden
iodopropynyl butylcarbamate is a preservative with broad fungicidal activity used in skin care products. It is recommended for use in difficult formulation systems.