Iodopropynyl butylcarbamate

281.09

281.09

259-627-5

603P14DHEB

3077

TSCA listed

DTXSID0028038

White to Almost white

29241990

38.33000

2.29950

white to off-white powder

1.606±0.06 g/cm3(Predicted)

64-68 °C(lit.)

321.8±25.0 °C(Predicted)

148.4ºC

1.525

168mg/L at 20℃

Refrigerator

0.005Pa at 25℃

LD50 orally in rats: 1580 mg/kg; dermally in rabbit: >2000 mg/kg; LC50 (96 hr) in bluegill sunfish, rainbow trout, bobwhite quail: 1.12, 0.31, >7683 ppm; LC50 (8 day) in mallard duck: >7182 ppm (Hansen)

Not classified

Sharp pungent odor

12.03±0.46(Predicted)

8.2×101mol/(m3Pa) at 25℃, HSDB (2015)

Hydroxyl radical reaction rate constant = 2.6X10-11 cu cm/molecule-sec at 25 °C /Estimated/

No rapid reaction with air. No rapid reaction with water.

Carbamates

Iodopropynyl 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.

Keep in dark place,Sealed in dry,2-8°C

III

9

3077

3

N

60-61-29

EZ0950000

N

Stable. Incompatible with strong oxidizing agents.

P260-P280-P304 + P340 + P312-P305 + P351 + P338 + P310-P403 + P233

50/53-50

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.

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.

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.

3077

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Some may burn but none ignite readily. Containers may explode when heated. Some may be transported hot. For UN3508, be aware of possible short circuiting as this product is transported in a charged state. (ERG, 2016)

|Danger|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P260, P261, P264, P270, P271, P272, P273, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P310, P311, P314, P321, P330, P333+P313, P363, P391, P403+P233, P405, and P501|H302+H332 (24.97%): Harmful if swallowed or if inhaled [Warning Acute toxicity, oral; acute toxicity, inhalation]|P260, P261, P264, P270, P271, P272, P273, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P310, P311, P312, P314, P321, P330, P332+P313, P333+P313, P362, P363, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 1780 companies from 40 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P261, P264, P270, P271, P272, P273, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P310, P311, P312, P321, P330, P332+P313, P333+P313, P362, P363, P391, P403+P233, P405, and P501|Warning|H335: May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]|P260, P261, P271, P304+P340, P312, P314, P403+P233, P405, and P501

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: SMALL FIRE: Dry chemical, CO2, water spray or regular foam. LARGE FIRE: Water spray, fog or regular foam. Do not scatter spilled material with high-pressure water streams. Move containers from fire area if you can do it without risk. Dike fire-control water for later disposal. FIRE INVOLVING TANKS: Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. (ERG, 2016)

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent dust cloud. Avoid inhalation of asbestos dust. SMALL DRY SPILL: With clean shovel, place material into clean, dry container and cover loosely; move containers from spill area. SMALL SPILL: Pick up with sand or other non-combustible absorbent material and place into containers for later disposal. LARGE SPILL: Dike far ahead of liquid spill for later disposal. Cover powder spill with plastic sheet or tarp to minimize spreading. Prevent entry into waterways, sewers, basements or confined areas. (ERG, 2016)

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. (ERG, 2016)

Iodopropynyl butylcarbamate has produced slight irritation in rabbits. However, it was not found to be either a skin sensitizer or a photo sensitizer in guinea pigs. Cosmetic formulations containing up to 0.125% of iodopropynyl butylcarbamate produce no significant irritation or sensitization reactions in human repeated insult patch tests. Iodopropynyl butylcarbamate did not cause crosssensitization reactions in patients who had demonstrated sensitivity to related dithiocarbamate compounds. In the European Union, it is approved as a preservative up to 0.05% and is not to be used in oral hygiene or lip care products. If the concentration exceeds 0.02% in leave-on products, a warning label must indicate that the product contains iodine.

LD50 Rat oral (female) 1.1 g/kg /99% Technical/ /from table/|LD50 Rat oral 1.5 g/kg /99% Technical/ /from table/|LD50 Rabbit dermal >2000 mg/kg /98% IPBC/ /from table/

/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.

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).

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).

The rate constant for the vapor-phase reaction of 3-iodo-2-propynyl butylcarbamate with photochemically-produced hydroxyl radicals has been estimated as 2.6X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 1.5 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). This substance is expected to undergo hydrolysis based on measured half-lives of 139 days at pH 7 and 0.98 days at pH 9(2). The half-life of 3-iodo-2-propynyl butylcarbamate was 13.3 hours in an aerobic, sterile, static sediment-water system(2,3). The primary hydrolysis metabolite of this substance is propargyl butyl carbamate(2,3).

An estimated BCF of 36 was calculated for 3-iodo-2-propynyl butylcarbamate(SRC), using a water solubility of 156 mg/L(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC), provided the compound is not altered physically or chemically once released into the environment(SRP).

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.

The Henry's Law constant for 3-iodo-2-propynyl butylcarbamate is estimated as 1.2X10-7 atm-cu m/mole(SRC) derived from its vapor pressure, 5.25X10-5 mm Hg(1), and water solubility, 156 mg/L(1). This Henry's Law constant indicates that 3-iodo-2-propynyl butylcarbamate is expected to be essentially nonvolatile from moist soil or water surfaces(2). 3-Iodo-2-propynyl butylcarbamate is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

Occupational exposure to 3-iodo-2-propynyl butylcarbamate may occur through inhalation and dermal contact with this compound at workplaces where 3-iodo-2-propynyl butylcarbamate is produced or used. (SRC)|The estimated daily exposure for handlers of 3-iodo-2-propynyl butylcarbamate in industrial settings ranges from 0.003-0.11 mg/kg/day for short and intermediate term exposures(1). Estimates range from 0.002-0.005 mg/kg/day for handlers in industrial settings that are chronically exposed. Short and intermediate term estimated daily exposures for handlers of 3-iodo-2-propynyl butylcarbamate in non-industrial settings range from 0.002-0.28 mg/kg/day for homeowners and from 0.09-1.30 mg/kg/day for occupational handlers. Estimated chronic exposures for occupational handlers in non-industrial settings range from 0.0009-0.33 mg/kg/day(1).

...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.

...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.

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Inhalation of material may be harmful. Contact may cause burns to skin and eyes. Inhalation of Asbestos dust may have a damaging effect on the lungs. Fire may produce irritating, corrosive and/or toxic gases. Some liquids produce vapors that may cause dizziness or suffocation. Runoff from fire control may cause pollution. (ERG, 2016)

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. (ERG, 2016)

Basic treatment: Establish a patent airway. 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 normal saline 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 ... . /Poison A and B/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/

/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-butylcarbamate

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/.

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

Cosmetics -> Preservative