Diiodomethyl p-tolyl sulfone

422.02

422.02

243-468-3

FDJ36QMI3H

DTXSID3032541

Tan powder at room temperature

2904909090

42.5

3.8

2.274 g/cm3

136 deg C (range of 149-152 deg C)

420.1°C at 760 mmHg

207.9ºC

1.751

In water, 0.1 to 1 mg/L (temperature not reported), technical grade

Store in a dry area. Keep container closed when not in use. /Amical Flowable Antimicrobial Agent/

9.6X10-7 mm Hg at 25 deg C /average of 1.87X10-6 mm Hg and 5.3X10-8 mm Hg reported values at 25 deg C/

Stable at room temperature and at 54 °C for 2 weeks ... stable for 8 years at ambient temperature, stable for 36 months at 30 °C and for 6 months at 40 °C|Henry's Law constant = = 5.3X10-8 atm-cu m/mole /estimated from vapor pressure and water solubility/|Hydroxyl radical reaction rate constant = 5.5X10-12 cu cm/molec-sec at 25 °C (est)

P260, P261, P264, P271, P273, P280, P284, P302+P352, P304+P340, P305+P351+P338, P310, P311, P314, P320, P321, P332+P313, P362, P391, P403+P233, P405, P501

H315

SRP: 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 air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.|SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.|Pesticide wastes are acutely hazardous. Improper disposal of excess pesticide, spray mixture, or rinsate is a violation of Federal Law. If these wastes cannot be disposed of by use according to label instructions, contact your State Pesticide or Environmental Control Agency, or the Hazardous Waste Representative at the nearest EPA Regional Office for guidance. /Amical Flowable Antimicrobial Agent/|Nonrefillable container: Do not reuse or refill this container. Triple rinse or pressure rinse container (or equivalent) promptly after emptying. Then offer recycling, if available, or puncture and dispose of in a sanitary landfill, or by incineration, or, if allowed by state and local authorities, by burning. If burned, stay out of smoke. /Amical Flowable Antimicrobial Agent/

USEPA/Office of Prevention, Pesticides and Toxic Substances; Reregistration Eligibility Decision Document - Diiodomethyl p-tolyl sulfone, EPA 739-R-08-002 (March 2008). 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.[Available from, as of April 4, 2016: http://www.epa.gov/pesticides/reregistration/status.htm]

|Danger|H315 (15.67%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P310, P311, P321, P332+P313, P362, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 305 companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Occupational handlers must wear chemical resistant gloves while handling diiodomethyl p-tolyl sulfone. /Amical Flowable Antimicrobial Agent/|Wear goggles, face shield or safety glasses. /Amical Flowable Antimicrobial Agent/

Do not get in eyes, on skin, or on clothing. ... Wash thoroughly with soap and water after handling and before eating, drinking, chewing gum, or using tobacco. /Amical Flowable Antimicrobial Agent/|SRP: Contaminated protective clothing should be segregated in a manner such that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. The completeness of the cleaning procedures should be considered before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at the end of shift, but should remain at employee's place of work for cleaning.|Remove contaminated clothing and wash clothing before reuse. /Amical Flowable Antimicrobial Agent/

Diiodomethyl p-tolyl a sulfone is classified as an eye corrosive (Toxicity Ca tegory I). For dermal irritation, Diiodomethyl p-tolyl sulfone is a low irritant (Toxicity Category IV) and is not classified as a dermal sensitizer.

IDENTIFICATION AND USE: Diiodomethyl p-tolyl sulfone (DIMPTS) is a tan powder at room temperature. It is an algaecide, bactericide, and fungicide. DIMPTS is used as a materials preservative in paints, air duct coatings, fire-retardant coatings, pigment dispersions, inks, emulsions, extender slurries, adhesives, caulks, sealants, rubbers, plastic, textiles, leather, paper production to protect pulp and slurries, paper/paperboard, and wetlap. It is also used as a wood preservative. HUMAN EXPOSURE AND TOXICITY: Corrosive: causes irreversible eye damage. Harmful if absorbed through the skin. ANIMAL STUDIES: Male and female rats and dogs were administered DIMPTS for 90-days via the diet. In rats, the only treatment-related finding was squamous metaplasia of the salivary gland duct in the 80 mg/kg/day group. In dogs, female body weights in the high-dose group were significantly lower than controls. Altered clinical pathology parameters were considered secondary to inflammatory changes observed in some of the dogs. Treatment-related alterations were found in the thyroid glands, salivary glands, GI-tract in the mid- and/or high-dose groups. DIMPTS was negative in the four in vitro and one in vivo genotoxicity assays. The toxicological effects noted in the two mammalian species are consistent with the principal toxic effects of iodide, and are proposed to arise from release of iodide from the DIMPTS molecule with toxic sequelae. DIMPTS caused dystocia, decreased neonatal survival and hypothyroidism in rat reproduction studies resembling the effects caused by iodide. One molecule of DIMPTS contains two iodine moieties that are hydrolyzed upon ingestion and systemically absorbed, suggesting iodide toxicity as a probable mode of action for the effects observed in rats. Female rats given DIMPTS had increased incidence of vulvar discharge and dystocia, decreased litter size, decreased body weights and feed consumption, increased thyroid weights, thyroid follicular cell hypertrophy with decreased colloid, decreased triiodothyronine, and increased thyroid stimulating hormone levels. DIMPTS pups had decreased neonatal survival and body weights. These effects were associated with elevated levels of iodide in milk and sera. In contrast, DIMPTS de-iodinated analogue did not produce similar effects in adult females or their offspring. In rats reproductive toxicity at 40 mg/kg/day consisted of increased post implantation loss, decreased gestation survival and two cases of dystocia, while litter size, pup survival/weight were affected at 10 and 40 mg/kg/day. Morphological examinations of fetuses revealed no evidence of teratogenesis.

LD50 Rat (male) dermal >20000 mg/kg

Diiodomethyl p-tolyl sulfone's production may result in its release to the environment through various waste streams; its use as an algeacide, bactericide and fungicide(1) will result in its direct release to the environment(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), a reported Koc value of 500(2) indicates that diiodomethyl p-tolyl sulfone is expected to have moderate mobility in soil(SRC). Volatilization of diiodomethyl p-tolyl sulfone from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.3X10-8 atm-cu m/mole(SRC), derived from its average vapor pressure, 9.6X10-7 mm Hg(2), and water solubility, 10 mg/L(2). Diiodomethyl p-tolyl sulfone is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(2). Diiodomethyl p-tolyl sulfone is susceptible to microbial degradation in soil as indicated by the formation of monoiodomethyl p-tolylsulfone and methyl p-tolylsulfone under aerobic and anaerobic conditions. Hydrolysis and metabolism half-lives at pH 7 and 9 for the parent ranged from 1.5-9.6 days(2).|AQUATIC FATE: Based on a classification scheme(1), a reported Koc value of 500(2) indicates that diiodomethyl p-tolyl sulfone is expected to have moderate adsorption to suspended solids and sediment(SRC). An aquatic metabolism study observed greater concentration in the aqueous phase versus sediment phase(2). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 5.3X10-8 atm-cu m/mole(SRC), derived from its average vapor pressure, 9.6X10-7 mm Hg(2), and water solubility, 10 mg/L(2). According to a classification scheme(4), an estimated BCF of 26(SRC), from its log Kow of 2.66(2) and a regression-derived equation(5), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Diiodomethyl p-tolyl sulfone is susceptible to microbial degradation in soil(2), suggesting that biodegradation may be an important environmental fate process in water(SRC). Diiodomethyl p-tolyl sulfone is stable to hydrolysis at pH 5, but degrades at pH 7 and 9 to form monoiodo-p-tolylsulfone with half-lives ranging from 1.5-9.6 days(2).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), diiodomethyl p-tolyl sulfone, which has an average reported vapor pressure of 9.6X10-7 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase diiodomethyl p-tolyl sulfone 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 2.9 days(SRC), calculated from its rate constant of 5.5X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase diiodomethyl p-tolyl sulfone may be removed from the air by wet or dry deposition(SRC). Diiodomethyl p-tolyl sulfone is not expected to absorb at wavelengths >290 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 diiodomethyl p-tolyl sulfone with photochemically-produced hydroxyl radicals has been estimated as 5.5X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 2.9 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Diiodomethyl p-tolyl sulfone degrades by hydrolysis and metabolism to form dehalogenated and demethylated compounds(2). It is stable to hydrolysis at pH 5, but degrades at pH 7 and 9 to form monoiodo-p-tolylsulfone with half-lives ranging from 1.5-9.6 days(2). Monoiiodomethyl p-tolyl sulfone was the terminal residue in hydrolysis and aqueous photodegradation studies(2). UV-visible spectra were observed at two absorptions peaks 200 and 233-234 nm and the spectra were run from 200 to 800 nm(2). Diiodomethyl p-tolyl sulfone is not expected to absorb at wavelengths >290 nm(3) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 26 was calculated in fish for diiodomethyl p-tolyl sulfone(SRC), using a log Kow of 2.66(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

The log Koc of diiodomethyl p-tolyl sulfone has been reported as 2.7(1), corresponding to a Koc of 500(SRC). According to a classification scheme(2), this Koc value suggests that diiodomethyl p-tolyl sulfone is expected to have moderate mobility in soil. Release to water from treated soil and wood are considered probable routes of dissipation to the environment(1).

The Henry's Law constant for diiodomethyl p-tolyl sulfone is estimated as 5.3X10-8 atm-cu m/mole(SRC) derived from its average vapor pressure, 9.6X10-7 mm Hg(1), and water solubility, 10 mg/L(1). This Henry's Law constant indicates that diiodomethyl p-tolyl sulfone is expected to be essentially nonvolatile from water surfaces(2). Diiodomethyl p-tolyl sulfone's estimated Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to occur(SRC). Diiodomethyl p-tolyl sulfone is not expected to volatilize from dry soil surfaces based upon its vapor pressure(SRC).

According to the 2006 TSCA Inventory Update Reporting data, the number of persons reasonably likely to be exposed in the industrial manufacturing, processing, and use of diiodomethyl p-tolyl sulfone is 1 to 99; the data may be greatly underestimated(1).|NIOSH (NOES Survey 1981-1983) has statistically estimated that 8,631 workers (2,461 of these were female) were potentially exposed to diiodomethyl p-tolyl sulfone in the US(1). The NOES Survey does not include farm workers. Occupational exposure to diiodomethyl p-tolyl sulfone may occur through inhalation and dermal contact with this compound at workplaces where diiodomethyl p-tolyl sulfone is produced or used. Use data indicate that the general population may be exposed to diiodomethyl p-tolyl sulfone via dermal contact with consumer products treated with products containing diiodomethyl p-tolyl sulfone(SRC).

Metabolism of diiodomethyl-p-tolylsulfone (DIMPTS) was investigated in rats to determine the role of iodide in its toxicity. Fischer 344 (F-344) (5 or 50 mg/kg) or Sprague Dawley (SD) (5 mg/kg) rats were gavaged with (14)C-DIMPTS or dermally applied with 5 mg/kg (F-344 only) and absorption, distribution, metabolism and excretion (ADME) determined. Additional experiments were conducted with its deiodinated analog (methyl-p-tolylsulfone, MPTS) in female F-344 rats (20 mg/kg) for comparison. Orally administered (14)C-DIMPTS was rapidly absorbed and eliminated in urine (92%). ... Dermally applied (14)C-DIMPTS remained undetectable in plasma with bioavailability approxamately 7%, only 5-7% of the dose was recovered in urine. ... The MPTS was rapidly absorbed from the GI tract, metabolized and eliminated in urine similar to that of DIMPTS. ...

Metabolism of diiodomethyl-p-tolylsulfone (DIMPTS) was investigated in rats to determine the role of iodide in its toxicity. Fischer 344 (F-344) (5 or 50 mg/kg) or Sprague Dawley (SD) (5 mg/kg) rats were gavaged with (14)C-DIMPTS or dermally applied with 5 mg/kg (F-344 only) and absorption, distribution, metabolism and excretion (ADME) determined. ... DIMPTS liberated one or both of its iodine atoms upon absorption. The rate of elimination of the liberated iodide from the systemic circulation was 2- to 3-fold slower in SD than F-344 rats, which resulted in higher bioavailability of iodide to SD rats. DIMPTS was primarily oxidized at the benzylic methyl moiety forming the corresponding benzoic acid. Glutathione conjugation on the sulfonyl methyl group, via displacement of I(-) was also observed. Overall 67-80% of the total iodine atoms were metabolically released from DIMPTS. ...

... Orally administered (14)C-DIMPTS was rapidly absorbed and eliminated in urine (92%). The elimination t(1/2) was 1-4 hr. ...

The mode of action (MOA) underpinning the reproductive toxicity of diiodomethyl-p-tolylsulfone (DIMPTS) is excess systemic iodide levels, resulting in hypothyroidism. This MOA evaluation also addresses the potential for toxicity and adverse health outcomes during critical windows of development for different tissues. The data indicate that testicular development in the neonate represents the tissue and life-stage that are most sensitive to iodide toxicity. Life-stage specific dosimetry appears to be a major determinant of this sensitivity, with the neonate being exposed to higher levels of iodide than the fetus during the period of testicular development, in particular Sertoli cell maturation and differentiation. While no reports could be found in the literature linking excess iodide exposure in humans to testicular toxicity, there is evidence that neonates born to mothers with excessive iodide intake do exhibit signs of transient hypothyroidism. Although there are major physiological and temporal differences in testicular development and Sertoli cell replication between the rat and human, it is not inconceivable that continuous long term exposures to excess iodide first from maternal milk and then in the diet through to the onset of puberty could affect testicular development. However, exposures to iodinated substances - such as DIMPTS - contribute less than 1% of the required daily iodide intake for normal fetal and neonatal development and, consequently, continuous exposure to excess iodide during the pre-pubertal period is unlikely. As exposures to DIMPTS are both very low and sporadic in nature it is not likely that they represent any risk to health at any life-stage.

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 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/|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/|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 TKO. Use 0.9% saline (NS) or lactated Ringer's (LR) 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 (Valium) or lorazepam (Ativan) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

/SIGNS AND SYMPTOMS/ Corrosive: causes irreversible eye damage. Harmful if absorbed through the skin. /Amical Flowable Antimicrobial Agent/|/OTHER TOXICITY INFORMATION/ The mode of action (MOA) underpinning the reproductive toxicity of diiodomethyl-p-tolylsulfone (DIMPTS) is excess systemic iodide levels, resulting in hypothyroidism. This MOA evaluation also addresses the potential for toxicity and adverse health outcomes during critical windows of development for different tissues. The data indicate that testicular development in the neonate represents the tissue and life-stage that are most sensitive to iodide toxicity. Life-stage specific dosimetry appears to be a major determinant of this sensitivity, with the neonate being exposed to higher levels of iodide than the fetus during the period of testicular development, in particular Sertoli cell maturation and differentiation. While no reports could be found in the literature linking excess iodide exposure in humans to testicular toxicity, there is evidence that neonates born to mothers with excessive iodide intake do exhibit signs of transient hypothyroidism. Although there are major physiological and temporal differences in testicular development and Sertoli cell replication between the rat and human, it is not inconceivable that continuous long term exposures to excess iodide first from maternal milk and then in the diet through to the onset of puberty could affect testicular development. However, exposures to iodinated substances - such as DIMPTS - contribute less than 1% of the required daily iodide intake for normal fetal and neonatal development and, consequently, continuous exposure to excess iodide during the pre-pubertal period is unlikely. As exposures to DIMPTS are both very low and sporadic in nature it is not likely that they represent any risk to health at any life-stage.

1-(diiodomethyl)sulfonyl-4-methyl benzene

Powder (technical grade active ingredient); flowable dispersion, wettable powder, and powder (end use products).|Amical 48 (The Dow Chemical Co.): Active ingredient: diiodomethyl p-tolyl sulfone 95%.|Amical WP Antimicrobial Agent (The Dow Chemical Co.): Active ingredient: diiodomethyl p-tolyl sulfone 48.45%.|Amical Flowable Antimicrobial Agent (The Dow Chemical Co.): Active ingredient: diiodomethyl p-tolyl sulfone 40.00%.|For more Formulations/Preparations (Complete) data for Diiodomethyl p-tolyl sulfone (8 total), please visit the HSDB record page.

Benzene, 1-[(diiodomethyl)sulfonyl]-4-methyl-: ACTIVE

Cosmetics -> Antimicrobial