3-Iodo-2-propynyl butylcarbamate

Cosmetic ingredients (Iodopropynyl Butylcarbamate) -> CIR (Cosmetic Ingredient Review)

Cosmetic ingredients (Iodopropynyl Butylcarbamate (IPBC)) -> CIR (Cosmetic Ingredient Review)

Preservative

1.575 g/mL

1.575 @25 °C

Off-white, dull color powder

White, crystalline powder

66 °C

66 °C

0.0000525 [mmHg]

5.25X10-5 mm Hg at 30 °C

0.0000525 [mm Hg] @30 °C

Danger

H302: 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.

Danger

H302+H332 (25.6%): Harmful if swallowed or if inhaled [Warning Acute toxicity, oral; acute toxicity, inhalation]

Chemical: Carbamic acid, butyl-, 3-iodo-2-propynyl ester

Carbamic 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/23059

Iodocarb: HSNO Approval: HSR002733 Approved with controls

Positive patch tests reported in worker in a paint factory and in patients sensitized by cosmetics; Animals 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]

USEPA/Office of Pesticide Programs; Reregistration 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.

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: 2725; Pesticide type: fungicide; Case Status: RED Approved 3/97; OPP 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 butylcarbamate; Data Call-in (DCI) Date(s): 4/30/91, 5/29/97; AI 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.

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.

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 quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

0.116 [mg/m3]

49 [mg/m3]

290 [mg/m3]

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.

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).

LC50 Anas platyrhyncos (Mallard duck, 10 days old) dietary >5620 ppm/8 days

LD50 Colinus virginianus (Northern bobwhite, 21 weeks old) oral 970 mg/kg/21 days

LD50 Colinus virginianus (Northern bobwhite, 23 weeks old) oral 749 mg/kg/14 days

LC50 Colinus virginianus (Northern bobwhite, 10 days old) dietary >5620 ppm/8 days

For more Ecotoxicity Values (Complete) data for 3-IODO-2-PROPYNYL BUTYLCARBAMATE (15 total), please visit the HSDB record page.

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).

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 ≤ 0.1%. IPBC should not be used in products intended to be aerosolized.

Safe for use in cosmetics, with qualifications

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 ≤ 0.1%. IPBC should not be used in products intended to be aerosolized.

Safe for use in cosmetics, with qualifications

3-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.

/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.

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)

/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).

3-Iodo-2-propynyl butyl carbamate's production may result in its release to the environment through various waste streams; it'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).

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: 2725; Pesticide type: fungicide; Case Status: RED Approved 3/97; OPP 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 butylcarbamate; Data Call-in (DCI) Date(s): 4/30/91, 5/29/97; AI 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.

...IPBC undergoes reductive dehalogenation followed by dealkylation to form the URM-9 and URM-10 metabolites. In addition, de-carboxylation following reductive dehalogenation yields carbon dioxide. Various other metabolites formed from dehalogenation are glucuronidated and constitute minor metabolites of IPBC.

The carbamates are hydrolyzed enzymatically by the liver; degradation products are excreted by the kidneys and the liver. (L793)

...IPBC was administered orally in 0.5% carboxymethylcellulose to groups of male and female Crl:CD/BR rats in the following manner: Groups of 5 male and 5 female rats (groups A and B) received either a single oral high dose of radiolabelled IPBC (125 mg/kg) or a repeated low oral dose of non-radiolabelled IPBC followed by a single radiolabelled dose (20 mg/kg). Separate groups of rats (9/sex/group, groups C and D) received single oral doses (20 and 125 mg/kg) of radiolabelled IPBC, and 3 rats/sex were sacrificed at 2, 4, and 120 hours post-dose for determination of tissue distribution of radioactivity. Urine, feces and expired air were collected at 24 hr intervals for groups A and B, while urine and feces were collected from groups C and D. Absorption of test chemical at the low and high dose was between 80-90% for all dose groups, as suggested by excretion data showing the majority of a dose eliminated through urine or exhaled air. Excretion of IPBC-derived radioactivity was mainly via the urine, with between 50-70% of an administered dose excreted by this route at 168 hours post-dose. Feces was a minor route of excretion in all dose groups (4-7% of the administered dose), while radiolabelled CO2 constituted between 18-24% of the administered dose. Repeated low oral dosing or a single high oral dose appeared to result in a decrease in the percentage of radioactivity excreted as 14-CO2 compared to a single low dose.

CIR ingredient: Iodopropynyl Butylcarbamate

CIR ingredient: Iodopropynyl Butylcarbamate (IPBC)

Used as a fungicide and mildewcide; Also used as a preservative in cosmetics, paints, coatings, wood, and metalworking fluids; [Merck Index]

Metal Machining [Category: Heat or Machine]

For 3-iodo-2-propynyl butylcarbamate (USEPA/OPP Pesticide Code: 107801) 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./

3-iodo-2-propynl butyl carbamate (IPBC) is a fungicide and antimicrobial used in both industrial processes and residential settings. IPBC is used in the following industrial products and processes: paint/adhesive/emulsion manufacturing, metal cutting fluids, oil recovery drilling mud/packer fluids, plastics manufacturing, textile manufacturing, ink manufacturing, paper coating, canvas manufacturing, and milled wood products manufacturing. IPBC is also a wood preservative used to combat fungal wood rot/decay. For residential use, IPBC can be applied with a paint brush, paint roller, and airless sprayer. IPBC is also applied to heating, ventilation and air conditioning (HVAC) ducts to control mold and fungi.

Polyphase P-100, an antisapstain wood preservative, ...contains 97% 3-iodo-2-propynyl butyl carbamate.

Trade and Other Names: Troysan Polyphase Anti-Mildew; Troysan Polyphase KK-108A; Permatox IBP; ASC 67000.

IPBC is formulated as solids and liquids (0.05 to 97% active ingredient). ...Formulation Types: Single Active Ingredient Products: Emulsifiable concentrate- 4-5.97%; Soluble concentrate liquid- 2.4-40%; Liquid ready to use- 0.4-0.8%; Soluble concentrate solid- 20-97%. Multiple Active Ingredient Products: Liquid ready to use- 0.05-0.5% + one other /active ingredient/.

All Other Chemical Product and Preparation Manufacturing

Carbamic acid, N-butyl-, 3-iodo-2-propyn-1-yl ester: ACTIVE