2-메르캅토벤조티아졸

Plastics & Rubber -> Rubber Additives

Rubber

Agrochemicals -> Pesticide active substances

Active substance -> EU Pesticides database: Not approved

Pesticides -> Biocides -> Transformation products

log Kow = 2.41

2.42

2.41

Disagreeable odor

Distinctive odor (depends on degree of purification)

1.42 at 68 °F (NTP, 1992) - Denser than water; will sink

1.42 g/cu cm at 20 °C

1.42 g/cm³

1.42 @ 20°C

Pale, yellow monoclinic needles or leaflets

Yellowish powder

Pale yellow monoclinic needles from alcohol or methanol

Cream to light yellow solid

less than 1 mg/mL at 66 °F (NTP, 1992)

In water at 25 °C, 51 mg/L (pH 5), 118 mg/L (pH 7), 900 mg/L (pH 9)

In pure water, 120 mg/L at 24 °C; in buffered creek water at 24 °C, 190 mg/L (pH 6.5), 230 mg/l (pH 7.5), 260 mg/L (pH 8.5)

Solubility at 25 °C (g/100 mL) in alcohol: 2.0; ether 1.0; acetone 10.0; benzene 1.0; carbon tetrachloride <0.2; naphtha <0.5. Moderately soluble in glacial acetic acid. Soluble in alkalies and alkali carbonate solutions

Soluble in dilute caustic soda, alcohol, acetone, benzene, chloroform; insoluble in water and gasoline.

For more Solubility (Complete) data for 2-MERCAPTOBENZOTHIAZOLE (6 total), please visit the HSDB record page.

392 °F (NTP, 1992)

392 °F

243 °C

Warning

H317: May cause an allergic skin reaction [Warning Sensitization, Skin]

P261, P272, P273, P280, P302+P352, P321, P333+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

Warning

H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]

P261, P272, P273, P280, P302+P352, P321, P333+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

Chemical: 2(3H)-Benzothiazolethione

Hazard Traits - Carcinogenicity

2(3H)-Benzothiazolethione is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2(3H)-Benzothiazolethione 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)

2007/442

Status: Active Update: 31-03-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/13432

2-Mercaptobenzothiazole: Does not have an individual approval but may be used under an appropriate group standard

This chemical is combustible. (NTP, 1992)

Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air.

A rubber accelerator, MBT is the most common cause of shoe allergy and second to the thiurams as the cause of glove contact dermatitis. [Marks, p. 100-2] An eye irritant; May cause skin sensitization; [ICSC] Mice show severe liver damage after high-dose feeding for 1 week; [AIHA] See Carcinogenicity of some industrial chemicals, Volume 115. [IARC, News Release, 23 February 2016]

2-Mercaptobenzothiazole is an indirect food additive for use only as a component of adhesives.

2-Mercaptobenzothiazole solution. Opthalmic and topical dosage form new animal drugs. ... Indications for use. For dogs as an aid in the treatment of hot spots (moist dermatitis) and as first aid for scrapes and abrasions.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Mercaptobenzothiazole is included on this list. Effective date: 12/28/84; Sunset date: 12/28/94.

All persons who manufacture (including import or manufacture as a byproduct) or process or intend to manufacture or process one or more of the substances in paragraph c of this section, other than as an impurity, after July 29, 1988, to the end of the reimbursement period shall submit letters of intent to conduct testing, submit study plans, conduct tests, and submit data, or submit exemption applications for those substances they manufacture or process, or intend to manufacture or process, as specified in this section, subpart A of this part, and parts 790 and 792 of this chapter for single-phase rulemaking. Mercaptobenzothiazole is included on this list. Required testing: chemical fate, environmental effects, and health effects.

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be use. (NTP, 1992)

Use water spray, dry powder, foam, carbon dioxide.

Fresh air, rest.

Wear protective gloves when administering first aid. Remove contaminated clothes. Rinse and then wash skin with water and soap.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth.

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Suitable extinguishing media: Use water spray, alchohol-resistant foam, dry chemical or carbon dioxide.

Advice for firefighters: Wear self contained breathing apparatus for fire fighting if necessary.

Personal precautions, protective equipment and emergency procedure: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Avoid breathing dust.

Enviromental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided.

Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

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.

Personal protection: face shield and particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered sealable containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.

Precautions for safe handling: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Provide appropriate exhaust ventilation at places where dust is formed. Normal measures for preventative fire protection.

SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

Adjuvants are formulation factors that are used to enhance pharmacologic or toxic effect of active ingredient. ... Examples of adjuvants used in toxicologic formulations incl ... use of mercaptobenzothiazole to enhance fungicidal activity of dithiocarbamates

LC50; Species: Ceriodaphnia dubia (Water Flea) age <24 hr neonate; Conditions: freshwater, renewal, 24.1-25.0 °C, pH 7.35-8.35, hardness 85-100 mg/L CaCO3, alkalinity 70-85 mg/L CaCO3; Concentration: 1250 ug/L for 7 days (95% confidence interval: 1140-1360 ug/L) /98% purity/

LC50; Species: Ceriodaphnia dubia (Water Flea) age <24 hr neonate; Conditions: freshwater, static, 24.1-25.0 °C, pH 7.35-8.35, hardness 85-100 mg/L CaCO3, alkalinity 70-85 mg/L CaCO3; Concentration: 4190 ug/L for 48 hr (95% confidence interval: 3520-5090 ug/L) /98% purity/

LC50; Species: Lepomis macrochirus (Bluegill); Conditions: freshwater, static; Concentration: 2300 ug/L for 24 hr /formulation/

LC50; Species: Lepomis macrochirus (Bluegill); Conditions: freshwater, static; Concentration: 2000 ug/L for 48 hr /formulation/

For more Ecotoxicity Values (Complete) data for 2-MERCAPTOBENZOTHIAZOLE (10 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), a Koc range of 326-3560 measured in a variety of soils(2) indicates that 2-mercaptobenzothiazole is expected to have moderate to slight mobility in soil(SRC). The pKa of 2-mercaptobenzothiazole is 7.03(2), indicating that this compound will exist partially in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(3). Volatilization of 2-mercaptobenzothiazole from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.1X10-11 atm-cu m/mole(SRC), derived from its vapor pressure, 2.25X10-8 mm Hg(2), and water solubility, 120 mg/L(4). 2-Mercaptobenzothiazole is not expected to volatilize from dry soil surfaces based upon its vapor pressure(SRC). A 2.5% of theoretical BOD using activated sludge in the Japanese MITI test suggests that 2-mercaptobenzothiazole is not readily biodegradable(5). Results of other biodegradation screening tests also indicate that 2-mercaptobenzothiazole is resistant to environmental biodegradation(2). High concentrations of 2-mercaptobenzothiazole (>50 ppm) may be toxic to the microorganisms and inhibit biodegradation(6); 2-mercaptobenzothiazole can be susceptible to biodegradation at low concentrations with acclimation(6). The half-life of 2-mercaptobenzothiazole in three standard soils ranged from 92 to 248 days(7). 2-Mercaptobenzothiazole absorbs at wavelengths >290 nm(8) and, therefore, may be susceptible to direct photolysis by sunlight(SRC). Aqueous photolysis studies have observed direct photolysis half-lives of less than one day(2,4); therefore, photodegradation is expected to occur on soil surfaces exposed to sunlight(SRC).

AQUATIC FATE: Based on a classification scheme(1), a Koc range of 326-3560 measured in a variety of soils(2) indicates that 2-mercaptobenzothiazole is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon a an estimated Henry's Law constant of 4.1X10-11 atm-cu m/mole(SRC), derived from its vapor pressure, 2.25X10-8 mm Hg(2), and water solubility, 120 mg/L(4). A pKa of 7.03(2) indicates 2-mercaptobenzothiazole will exist partially in the anion form at pH values of 5 to 9(SRC). In the environmental pH range, 2-mercaptobenzothiazole can exist in the ionized thiolate form as well as the two unionized thiol and thione tautomers(5). The thione form is believed to be responsible for its ligand formation with several metals, and this could affect its behavior in aquatic systems(5). According to a classification scheme(6), a measured BCF of less than 8 in carp (Cyprinus carpio)(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). A 2.5% of theoretical BOD using activated sludge in the Japanese MITI test suggests that 2-mercaptobenzothiazole is not readily biodegradable(7). Results of other biodegradation screening tests also indicate that 2-mercaptobenzothiazole is resistant to environmental biodegradation(2). High concentrations of 2-mercaptobenzothiazole (>50 ppm) may be toxic to the microorganisms and inhibit biodegradation(8); 2-mercaptobenzothiazole can be susceptible to biodegradation at low concentrations with acclimation(8). Aqueous photolysis tests indicate that 2-mercaptobenzothiazole is susceptible to direct photolysis with half-lives of <1 day to <1 hour (at the water surface) under full sunlight exposures at 30-40 N latitude(2,5). Test results indicate that hydrolysis is not an important fate process(2).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-mercaptobenzothiazole, which has a vapor pressure of 2.25X10-8 mm Hg at 20 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase 2-mercaptobenzothiazole 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 9.5 hours(SRC), calculated from its rate constant of 4.1X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase 2-mercaptobenzothiazole may be removed from the air by wet and dry deposition(SRC). 2-Mercaptobenzothiazole absorbs at wavelengths >290 nm(4) and, therefore, may be susceptible to direct photolysis by sunlight(SRC). Aqueous photolysis studies have observed direct photolysis half-lives of less than one day(2,5).

IDENTIFICATION AND USE: Mercaptobenzothiazole (MBT) is yellowish powder. It is not registered for current 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. Antioxidant and stabilizer added to polyether polymers to improve air aging and ozone resistance. MBT and its derivatives have been used to protect copper and copper alloys against corrosion. MBT is used as an indicator reagent for the photometric determination of Au, Cd, Cu, Pb, and Pd. It is also used as veterinary medication. HUMAN EXPOSURE AND TOXICITY: it can produce contact allergy in products such rubber condoms and rubber earplugs. A case of occupational allergic contact dermatitis and anaphylactic shock caused by rubber latex was described. Occupational exposure to MBT may result in hand dermatitis in hospital nurses and other medical personnel. Epidemiological investigations indicate that workers occupationally exposed to MBT have an increased risk of death from bladder cancer. ANIMAL STUDIES: Acute exposure in mice caused convulsions. No teratogenic effects were observed in fetuses of rats after 200 mg/kg of MBT ip on days 1-15 of gestation. Under the conditions of NTP 2 yr gavage studies, there was some evidence of carcinogenic activity of MTB for male rats, indicated by increased incidences of mononuclear cell leukemia, pancreatic acinar cell adenomas, adrenal gland pheochromocytomas, and preputial gland adenomas or carcinomas (combined). There was some evidence of carcinogenic activity for female rats, indicated by increased incidences of adrenal gland pheochromocytomas and pituitary gland adenomas. There was no evidence of carcinogenic activity of MBT for male mice dosed with 375 or 750 mg/kg. There was equivocal evidence of carcinogenic activity for female mice, indicated by increased incidences of hepatocellular adenomas or carcinomas (combined). MBT was not mutagenic in Salmonella typhimurium strains TA98, TA100, TA1535, or TA1537 with or without metabolic activation. In the presence of rat liver S9, MBT increased the frequency of chromosomal aberrations and sister chromatid exchanges in Chinese hamster ovary cells, as well as mutations at the TK locus of mouse L5178Y lymphoma cells. ECOTOXICITY STUDIES: MBT is almost nontoxic to birds on an acute oral basis and is only slightly toxic to birds on a dietary basis. MBT is highly toxic to freshwater fish and moderately toxic to aquatic invertebrates.

/BIRDS and MAMMALS/ 2-Mercaptobenzothiazole is almost nontoxic to birds on an acute oral basis and is only slightly toxic to birds on a dietary basis.

/AQUATIC SPECIES/ Rainbow trout, /exposure/ 89 days (69 days post-hatch) /at dose/ 0, 24, 48, 95, 190, 380 ug/L (nominal). /Results:/ Embryo viability in all concentrations ranged from 91 to 97%. Survival at the completion of the hatching period (day 31) in all concentrations ranged from 86% (380 ug/L) to 89% (24 ug/L). At termination, survival at all concentrations ranged from 90-95%. Larval length was the most sensitive indicator of toxicity, mean total length of larvae exposed to levels greater than 78 ug/L ranged from 51.3 - 52.0 mm and was significantly less than controls. The mean weight at the 380 ug/L level was 1.1582 g which was significantly reduced as compared to controls. The Maximum Acceptable Toxicant Concentration (MATC) was estimated to be greater than 41 ug/L and less than 78 ug/L.

/AQUATIC SPECIES/ Daphnia magna, /exposure/ flow-through, 21 days /at dose/ 0, 31, 63, 130, 250, 500 ug/L (nominal). /Results:/ On day 21, survival at 500 ug/L was 58% which was significantly less than controls. Survival at the remaining concentrations ranged from 93 to 98%. The 21-day EC50 was estimated to be greater than 470 ug/L. The cumulative number of offspring at concentrations less than 250 ug/L ranged from 89 to 138. The Maximum Acceptable Toxicant Concentration was estimated to be greater than 240 mg/L and less than 470 ug/L.

/AQUATIC SPECIES/ /2-Mercaptobenzothiazole/ is highly toxic to freshwater fish and moderately toxic to aquatic invertebrates...

For more Ecotoxicity Excerpts (Complete) data for 2-MERCAPTOBENZOTHIAZOLE (7 total), please visit the HSDB record page.

EPA has released the first beta version (version 0.5) of the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The beta version of the iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assays; Click on the "Chemical Explorer" button on the tool bar to see the data./[USEPA; ICSS Dashboard Application; Available from, as of December 8, 2014: http://actor.epa.gov/dashboard/]

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical.[Available from: http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=149-30-4]

2-Mercaptobenzothiazole was detected in effluent from an industrial dump at a concentration of about 0.03 mg/L(1). 2-Mercaptobenzothiazole was detected in wastewater from a tire plant(2). The effluent from a sewage treatment plant discharging into the River Lee in England contained trace amounts of 2-mercaptobenzothiazole(3). In a comprehensive survey of wastewater from 4000 industrial and publicly owned treatment works (POTWs) sponsored by the Effluent Guidelines Division of the U.S. EPA, 2-mercaptobenzothiazole was identified in one discharge each of the rubber processing and pesticides manufacturing industries at a concentration of 1.27 and 0.86 ppm, respectively(4). The concentration of 2-mercaptobenzothiazole in the effluent from a Kraft paper mill was 0.025 ppm(5). Mercaptobenzothiazole has been found at a concentration of 30 ug/L in the wastewater from a tire manufacturing plant(6). 2-Mercaptobenzothiazole has been detected in tannery wastewater(7). [

2-Mercaptobenzothiazole is an indirect food additive for use only as a component of adhesives.

2-Mercaptobenzothiazole solution. Opthalmic and topical dosage form new animal drugs. ... Indications for use. For dogs as an aid in the treatment of hot spots (moist dermatitis) and as first aid for scrapes and abrasions.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Mercaptobenzothiazole is included on this list. Effective date: 12/28/84; Sunset date: 12/28/94.

All persons who manufacture (including import or manufacture as a byproduct) or process or intend to manufacture or process one or more of the substances in paragraph c of this section, other than as an impurity, after July 29, 1988, to the end of the reimbursement period shall submit letters of intent to conduct testing, submit study plans, conduct tests, and submit data, or submit exemption applications for those substances they manufacture or process, or intend to manufacture or process, as specified in this section, subpart A of this part, and parts 790 and 792 of this chapter for single-phase rulemaking. Mercaptobenzothiazole is included on this list. Required testing: chemical fate, environmental effects, and health effects.

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 continued use. Under this pesticide reregistration program, EPA examines newer health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether the use of the pesticide does not pose unreasonable risk in accordance to newer saftey standards, such as those described in 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 than those on List C, and with List C containing pesticides of greater concern than those on List D. 2-Mercaptobenzothiazole is found on List B. Case No: 2380; Pesticide type: fungicide, antimicrobial; Case Status: RED Approved 09/94; 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): 2-mercaptobenzothiazole; AI Status: The active ingredient is no longer contained in any registered products. Thus, we characterize it as "cancelled."

Absorption, tissue distribution & excretion of (14)C 2-mercaptobenzothiazole was investigated after admin to carp. The radioactive chemical in bile was determined to be benzothiazole-2-mercaptoglucuronide.

Cysteine conjugate beta-lyases, enzymes that are present in mammalian liver, kidneys, and intestinal microflora, were exploited recently for site selective delivery of 6-mercaptopurine to the kidneys. In this study, in vivo cysteine conjugate beta-lyase activity was assessed using S-(2-benzothiazolyl)-L-cysteine. 2-Mercaptobenzothiazole and 2-mercaptobenzothiazole S-glucuronic acid were major metabolites of S-(2-benzothiazolyl)-L-cysteine in rat liver, kidney, plasma, and urine. Total metabolite concn in liver, kidney, or plasma at 30 min were similar and were higher than that detected at 3 hr; metabolites were mostly in the glucuronide form. The portions of metabolites excreted in urine at 8 and 24 hr were nearly 93 and 99% of that excreted at 40 hr, respectively. Pretreatment of rats with aminooxyacetic acid did not alter kidney, liver, plasma, or urinary metabolite concn. The portion of the S-(2 benzothiazolyl)-L-cysteine dose excreted as metabolites at 24 hr was independent of the S-(2-benzothiazolyl)-L- cysteine dose (100-400 umol/kg), age (5-12 wk), or sex of the rats. The rates of in vitro S-(2-benzothiazolyl)-L- cysteine metabolism by guinea pig hepatic and renal cysteine conjugate beta-lyases were slower than those of rats, but the portion of the S-(2-benzothiazolyl)-L- cysteine dose recovered as metabolites in guinea pig urine at 24 hr was nearly 60%, which was nearly 2 fold higher than that recovered in urine of rats, mice, or hamsters. The amounts of total metabolites excreted into urine by mice or hamsters were similar, but the portion of metabolites that was in the glucuronide form in hamster urine was higher than that in mouse urine.

The metabolic fate of the sulfur atom in the sulfhydryl group of 2-thiobenzothiazole metabolites was examined in a series of experiments in rats using (14)C and (35)S labeled L-cysteine and 2-thiobenzothiazole metabolites. Male Wistar rats were orally administered (35)S labeled 2-mercaptobenzothiazole. Glutathione conjugates of 2-mercaptobenzothiazole from biliary metabolites were determined in rat liver in vitro. The (35)S retention ratios in 2-mercaptobenzothiazole was over 90%.

Renal cysteine conjugate beta-lyase catalyzes the bioactivation of nephrotoxic cysteine S-conjugates. Cysteine conjugate beta-lyase activity is present in both renal cytosolic and mitochondrial fractions, and, although the cytosolic cysteine conjugate beta-lyase is identical to glutamine transaminase K, the mitochondrial cysteine conjugate beta-lyase has not been characterized. Because cysteine conjugate beta-lyase is a pyridoxal phosphate dependent enzyme, pyridoxamine phosphate formation may occur during the metabolism of cysteine S-conjugates. In this study, the effects of alpha-ketoacids, which may convert the pyridoxamine phosphate form of the enzyme to the pyridoxal phosphate form, on the metabolism and cytotoxicity of cysteine S-conjugates were examined; the pyridoxamine phosphate enzyme is catalytically inactive in beta-elimination reactions, but is catalytically active in transamination reactions. Both alpha-keto-gamma-methiolbutyrate and alpha-ketobutyrate enhanced the metabolism of S-(2-benzothiazolyl)-L-cysteine to 2-mercaptobenzothiazole by rat renal cytosol or mitochondria. alpha-Keto-gamma-methiolbutyrate and phenylpyruvate potentiated both the cytotoxicity of S-(1,2-dichlorovinyl)-L-cysteine in isolated rat renal proximal tubular cells and the inhibition of mitochondrial respiration produced by S-(1,2-dichlorovinyl)-L-cysteine. These results are consistent with the formation of pyridoxamine phosphate during the renal cytosolic or mitochondrial metabolism of cysteine S-conjugates Mitochondrial cysteine conjugate beta-lyase was previously localized in the outer membrane. To examine whether cysteine conjugate beta-lyase activity is present in mitoplasts, but in the pyridoxamine phosphate form, the effects of alpha-keto-gamma-methiolbutyrate on the metabolism of S-(2-benzothiazolyl)-l-cysteine to 2-mercaptobenzothiazole and on the S-(1,2-dichlorovinyl)-L-cysteine induced inhibition of state 3 respiration in mitoplasts were studied. The majority of the mitochondrial cysteine conjugate beta-lyase activity was present in the outer membrane, and the specific activity of the outer membrane cysteine conjugate beta-lyase was greater than that of the mitoplast cysteine conjugate beta-lyase. alpha-Keto-gamma-methiolbutyrate produced equivalent stimulation of cysteine conjugate beta-lyase activity in intact mitochondria, in mitochondrial outer membranes, and in mitoplasts and potentiated S-(1,2-dichlorovinyl)-L- cysteine induced inhibition of respiration in intact mitochondria, but not in mitoplasts. These results provide additional evidence for the central role of cysteine conjugate beta-lyase in the bioactivation of nephrotoxic cysteine S-conjugates.

5RLR54Z22K

2-MERCAPTOBENZOTHIAZOLE

Established Pharmacologic Class [EPC] - Standardized Chemical Allergen

Physiologic Effects [PE] - Increased Histamine Release

Physiologic Effects [PE] - Cell-mediated Immunity

Chemical Structure [CS] - Allergens

When carp were starved after admin of (14)C-2-mercaptobenzothiazole, the radioactivity in the intestine was 45% of dose after 1 hr, in bile 9% & in other tissues was less than 0.05% of dose after 72 hr. When carp were fed after admin of (14)C 2-mercaptobenzothiazole, radioactivity in bile was less than 0.3% & in other tissues was negligible in amt after 72 hr. About 100% of dose was excreted into water.

/In/ 4 males; 4 females Rats /exposure/ dermal (topical), 96 hr/at dose/ 0.0361, 0.0336 mg/kg /resulted in/ More of the radioactive test material could be removed by washing the skin of guinea pigs than by washing the skin of rats. At 96 hours, 16.1 and 17.5% of the dose was absorbed by male and female rats, respectively. Male and female rats dosed topically with the test material excreted 11.9 and 13.4%, respectively, in the urine and 0.980 and 0.641% of the dose in the feces.

/In/ 4 female guinea pigs/exposure/ dermal (topical), 96 hr/at dose/ 0.0361, 0.0336 mg/kg /resulted in/ More of the radioactive test material could be removed by washing the skin of guinea pigs than by washing the skin of rats. At 96 hours 38.4% of the dose was absorbed. Female guinea pigs dosed topically with the test material excreted 33.3% in the urine and 0.389% of the dose in the feces.

/In/ 4 male, 4 female rats/exposure/ oral (gavage), 96 hr /at dose/ 0.592, 55.5 mg/kg /resulted in/ High-dose test animals exposed to 14C-MBT and 14C MBTS (2-mercaptobenzothiazole and 2- mercaptobenzothiazole disulfide, respectively) excreted (within 96 hours) 72.1 to 106% of the administered dose in urine, and 4.03 to 10.3% was excreted in the feces. A small portion (0.423 to 2.04%) of the dose remained associated with the erythrocytes. Low-dosed animals retained a higher percent of the dose in whole blood and plasma than did the high-dose animals.

For more Absorption, Distribution and Excretion (Complete) data for 2-MERCAPTOBENZOTHIAZOLE (6 total), please visit the HSDB record page.

Nonrubber sources of exposure include metalworking fluids, antifreezes, greases, anticorrosive agents, adhesives, detergents, and veterinary products. [Marks, p. 101] Allergic contact dermatitis in shoemakers; [Marks] A known skin sensitizer, mercaptobenzothiazole has largely been replaced as an anti-corrosion agent in metalworking fluids. [Kanerva, p. 717] Metal indicators are organic compounds that form specifically colored metal ion complexes in aqueous media. These dye reactions can be employed for detection of the equivalence point in volumetry (complexometry), as well as for concentration determinations in colorimetry or photometry. 2-Mercaptobenzothiazole is used for the photometric determination of Au, Cd, Cu, Pb, and Pd. [Ullmann] Used in leather tanning; [PMID 21938525]

Metal Machining [Category: Heat or Machine]

For 2-mercaptobenzothiazole (USEPA/OPP Pesticide Code: 051701) there are 0 labels match. /SRP: Not registered for current 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./

The active ingredient is no longer contained in any registered products ... "cancelled."

FUNGICIDE FOR PRESERVING TEXTILES /SRP: FORMER USE/

Vulcanization accelerator for rubber (requires use of stearic acid for full activation), tire treads and carcasses, mechanical specialities, etc., ... corrosion inhibitor in cutting oils and petroleum products, extreme pressure additive in greases.

(1975) 1.90X10+7 GRAMS (PRINCPL CUSTMS DISTS)

(1977) 1.00X10+7 GRAMS (PRINCPL CUSTMS DISTS)

2023: 850,000 - <1,000,000 lb

(1975) 1.20X10+9 GRAMS

(1977) 2.72X10+9 GRAMS (SALES)

2(3H)-Benzothiazolethione is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: 2(3H)-Benzothiazolethione. Aggregated National Production Volume: 10 to < 50 million pounds.

Non-confidential 2012 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: 2(3H)-Benzothiazolethione. National Production Volume: 500,000 - 1,000,000 lb/yr.

Prepared industrially by reacting aniline, carbon disulfide, and sulfur at elevated pressure and temperature.

2-Mercaptobenzothiazole (MBT) is prepared by heating aniline, carbon disulfide, and sulfur in an autoclave at elevated temperature and pressure. Tars from the reaction can be removed by taking the crude MBT up in water by making the sodium salt, clarifying the solution, and then precipitating pure MBT with acid.

Grade: Technical; 97%.

Nuodex 84 contains the sodium salt for use in water base adhesives, paper sizings. Niacides are mixtures with carbamate fungicides for control of apple scab and rust.

Animal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients

Pesticides -> Biocides -> Transformation products

INDUSTRIAL

Not Known or Reasonably Ascertainable

2(3H)-Benzothiazolethione: ACTIVE

It is weak acid & forms salts with bases ... these salts are effective in mildew-proofing of fabrics, in slime & algae control, &, in case of dimethyldithiocarbamate salts, as seed treatment & foliar fungicide for fruits & vegetables.

Sodium salt (eg, Nacap, 50% soln) is corrosion inhibitor in antifreeze, coolants & other aqueous systems where corrosion is problem, particularly with copper & brass. Monoethanolamine salt ... & laurylpyridinium salt ... are marketed as commercial fungicides & bactericides.