21564-17-0N#CSCSc1nc2ccccc2s1TUBQDCKAWGHZPF-UHFFFAOYSA-NTCMTB is a wood preservative, marine biocide, contact fungicide, and as a preservative in paint.
21564-17-0DTXSID6032647CHEMBL1903976Fungicides
Active substance -> EU Pesticides database: Not approved
Pesticides -> Fungicides
Pesticide (TCMTB) -> USDA PDB
log Kow = 3.23 at 20 °C
3.3
3.12
Pungent
Strong sour and pungent odor (like mineral oil)
1.05 at 25 °C (c = 0.30)
Relative density (water = 1): 1.4
Oil
Vivid orange liquid
In water, 125 mg/L at 24 °C
Soluble in most organic solvents
Solubility in water, g/100ml: 0.0033
191 °C (decomposes)
>120 °C
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Danger
H302: Harmful if swallowed [Warning Acute toxicity, oral]
P260, P261, P264, P264+P265, P270, P271, P272, P273, P280, P284, P301+P317, P302+P352, P304+P340, P305+P351+P338, P316, P320, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Danger
H302+H312 (19.7%): Harmful if swallowed or in contact with skin [Warning Acute toxicity, oral; acute toxicity, dermal]
P260, P261, P264, P264+P265, P270, P271, P272, P273, P280, P284, P301+P317, P302+P352, P304+P340, P305+P351+P338, P316, P317, P320, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Chemical: Thiocyanic acid, (2-benzothiazolylthio)methyl ester
TCMTB (Busan 72) is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)
2002/2076
2-(Thiocyanomethylthio) benzothiazole: HSNO Approval: HSR003164 Approved with controls
The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)
Decomposed by heating forming hydrogen cyanide, nitrogen oxides, and sulfur oxides; A skin irritant; Corrosive to eyes; May cause skin sensitization; [ICSC] Highly irritating to eyes and skin; A skin sensitizer; Possible human carcinogen; Not neurotoxic; Elevation of liver enzymes in chronic dog studies; [EPA REDs] A skin and eye irritant; May cause skin sensitization; [eChemPortal: ESIS]
TCMTB has several metabolites, including 2-mercaptobenzothiazole (2-MBT) and 2-benzothiazolesulfonic acid (2-BTSA).
... Three different doses of TCMTB in olive oil were given to male rats by gavage for 3 weeks. Urine was collected daily and the metabolites were analysed as thioethers by derivatization with pentafluorobenzyl-bromide by gas chromatography-mass spectrometry. The parent chemical was not detected in urine samples, but two metabolites of TCMTB were identified. 2-Mercaptobenzothiazole (2-MBT) was the main metabolite, and its excretion varied according to the dose. The second metabolite was 2-(mercaptomethylthio)benzothiazole. The amount of 2-MBT excreted in rat urine was 66 +/- 12% (SD), 51 +/- 20% and 44 +/- 9% for TCMTB doses of 15, 75 and 150 mg/kg, respectively. Two doses, 75 and 150 mg/kg, caused diuresis in rats during the 1 week of dosing. During the 3-week TCMTB treatment, rat liver microsomal CYP enzyme profile was not significantly changed.
Organic nitriles are converted into cyanide ions through the action of cytochrome P450 enzymes in the liver. Cyanide is rapidly absorbed and distributed throughout the body. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide metabolites are excreted in the urine. (L96)
Industrial antimicrobial used instead of chlorophenols; Used as a wood preservative, marine biocide, and fungicide; [Merck Index] Used as a contact fungicide for barley, cotton, corn, oats, rice, sorghum, sugar beets, safflower, and wheat; in seed treatments for cereals, corn, cotton, legumes, rice, sorghum, and sugar beets; as preservative in paints and leather production; [HSDB] Used as a wood preservative, biocide (pulp & paper mills, sewage systems), product preservative and slimicide (paper, leather, paint, carpet, textiles, wallpaper), and seed treatment pesticide; [EPA REDs]
Pulp and Paper Processing [Category: Industry]
For 2-(benzothiazolylthio)methyl thiocyanate (USEPA/OPP Pesticide Code: 035603) 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./
현재 필터 조건에 해당하는 반응 기록이 없습니다.
불러오는 중…
0.00000031 [mmHg]
9.0X10-6 mm Hg at 25 °C
Brown Oil
USEPA/Office of Prevention, Pesticides and Toxic Substances; Reregistration Eligibility Decision Document - 2-(Thiocyanomethylthio)-benzothiazole (TCMTB) EPA 739-R-05-003 (August 2006). 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 November 4, 2014: http://www.epa.gov/pesticides/reregistration/status.htm]
Tolerances are established for residues of the fungicide 2-(thiocyanomethylthio)benzothiazole in or on the following food commodities:[Table#5974]
The Agency has completed its assessment of the dietary, occupational, drinking water, and ecological risks associated with the use of pesticide products containing the active ingredient TCMTB. Based on a review of these data and on public comments on the Agency's assessments for the active ingredient TCMTB, the Agency has sufficient information on the human health and ecological effects of TCMTB to make decisions as part of the tolerance reassessment process under FFDCA and reregistration process under FIFRA, as amended by FQPA. The Agency has determined that TCMTB-containing products are eligible for reregistration provided that: (i) current data gaps and confirmatory data needs are addressed; (ii) the risk mitigation measure outlined in this document is adopted; and (iii) label amendments are made to reflect this measure. Label changes are described in Section V. Appendix A summarizes the uses of TCMTB that are eligible for reregistration. ... Based on its evaluation of TCMTB, the Agency has determined that TCMTB products, unless labeled and used as specified in this document, would present risks inconsistent with FIFRA. Accordingly, should a registrant fail to implement the risk mitigation measure identified in this document, the Agency may take regulatory action to address the risk concerns from the use of TCMTB. If all changes outlined in this document are incorporated into the product labels, then all current risks for TCMTB will be substantially mitigated for the purposes of this determination. Once an Endangered Species assessment is completed, further changes to these registrations may be necessary.
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 safeey 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-(Thiocyanomethylthio)benzothiazole is found on List B. Case No: 2625; Pesticide type: fungicide, antimicrobial; Case Status: PreRED - OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the RED document.; Active ingredient (AI): 2-(Thiocyanomethylthio)benzothiazole; Data Call-in (DCI) Date(s): 06/30/91, 10/13/95; AI Status: The producers of the pesticide have made commitments to conduct the studies and pay the fees required for reregistration, and are meeting those commitments in a timely manner.
Acute Tox. 4 (100%)
Eye irritation - category 2
Flammable liquids - Category 4
Flammable liquids - Category 4
Flammable agents - 2nd degree
Acute Tox. 2 *
Fresh air, rest.
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.
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity 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 and plant life; and conformance with environmental and public health regulations.
Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Do NOT let this chemical enter the environment.
... 2-thiocyanomethylthio-benzothiazole) /was/ determined in human urine collected from general populations in seven countries (the U.S., Greece, Vietnam, Korea, Japan, China, and India). ...
A previously unknown pollutant in river water was identified to be 2-mercaptobenzothiazole (2-MBT) by interpretation and simulation of its GC/LRMS spectrum. Further GC/HRMS measurement of the isotope composition of the molecular ion verified this structure. 2-MBT is a well-known agent for corrosion inhibition and a stable metabolite of several other benzothiazoles. The present 2-MBT trace was most probably a metabolite of the wood preservative TCMTB which leaked from an upstream sawmill. The metabolite had been detected earlier in urine of the sawmill workers, but now was identified in the recipient water environment for the first time.
LC50; Species: /Lepomis macrochirus/ (Bluegill sunfish); Concentration: 0.047 ppm for 96 hr /60% formulation (Busan 72)/ /Conditions of bioassay not specified/
LC50; Species: /Oncorhynchus mykiss/ (Rainbow trout); Concentration: 0.029 ppm for 96 hr /60% formulation (Busan 72)/ /Conditions of bioassay not specified/
LC50; Species: /Colinus virginianus/ (Bobwhite quail); >10,000 ppm/ 96 hr /60% formulation (Busan 72)/ /Conditions of bioassay not specified/
LD50; Species: Duck oral 1310 mg/kg
For more Ecotoxicity Values (Complete) data for 2-(Thiocyanomethylthio)benzothiazole (24 total), please visit the HSDB record page.
TERRESTRIAL FATE: Based on a classification scheme(1), Koc values ranging from 282 to 7,896(2,3) indicate that 2-(thiocyanomethylthio)benzothiazole is expected to have moderate to no mobility in soil(SRC). Volatilization of 2-(thiocyanomethylthio)benzothiazole from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 7.1X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 9X10-6 mm Hg(3), and water solubility, 40 mg/L(4). 2-(Thiocyanomethylthio)benzothiazole is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure. A 0% of theoretical BOD using activated sludge in the Japanese MITI test indicates that 2-(thiocyanomethylthio)benzothiazole is not readily biodegradable(5). Using OECD Method 301B (CO2 Evolution Modified Sturm Test), 96% of initial 2-(thiocyanomethylthio)benzothiazole degraded by day 28(3); however, it took >10 days for the degradation to increase from 10 to 60%, thereby classifying the compound as not readily biodegradable under the conditions of the test(3). 2-(Thiocyanomethylthio)benzothiazole is susceptible to aqueous hydrolysis in moist alkaline soil(3). A photolysis half-life of 151.0 hrs on soil was reported using soil irradiated 12 hrs/day(6). A soil aerobic metabolism half-life of 1.4 days was reported(6).
AQUATIC FATE: Based on a classification scheme(1), Koc values ranging from 282 to 7,896(2,3) indicate that 2-(thiocyanomethylthio)benzothiazole is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(4) based upon an estimated Henry's Law constant of 7.1X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 9X10-6 mm Hg(3), and water solubility, 40 mg/L(5). According to a classification scheme(6), a BCF range of <14 to 268 measured in fish(3,7), suggests the potential for bioconcentration in aquatic organisms ranges from low to high. A 0% of theoretical BOD using activated sludge in the Japanese MITI test indicates that 2-(thiocyanomethylthio)benzothiazole is not readily biodegradable(7). Using OECD Method 301B (CO2 Evolution Modified Sturm Test), 96% of initial 2-(thiocyanomethylthio)benzothiazole degraded by day 28(3); however, it took >10 days for the degradation to increase from 10 to 60%, thereby classifying the compound as not readily biodegradable under the conditions of the test(3). A 95% degradation in 9 to 12 days has been observed using a mixed culture pilot plant designed for treatment of tannery wastes(8). 2-(Thiocyanomethylthio)benzothiazole was stable to hydrolysis in a sterilized buffer aqueous system at pH of 5 and 7; however, hydrolysis half-lives of 1.8 and 2.1 days were observed at pH 9 and 25 deg(9). A hydrolysis half-life of about one month was measured in seawater at 24 °C(5). Direct photolysis half-lives of less than one day are reported for 2-(thiocyanomethylthio)benzothiazole in pure water solutions under full sunlight conditions(5). 2-(Thiocyanomethylthio)benzothiazole undergoes direct photolysis in sunlight to produce 2-mercaptobenzothiazole (MBT) and benzothiazole(5).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-(thiocyanomethylthio)benzothiazole, which has a vapor pressure of 9X10-6 mm Hg at 25 °C(2) will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase 2-(thiocyanomethylthio)benzothiazole 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 4 hrs(SRC), calculated from its rate constant of 1.0X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase 2-(thiocyanomethylthio)benzothiazole may be removed from the air by wet and dry deposition(SRC). 2-(Thiocyanomethylthio)benzothiazole has measured direct photolysis half-lives of less than one day in aqueous solution(4), therefore, it is expected to be susceptible to direct photolysis by sunlight in air(SRC).
IDENTIFICATION AND USE: Thiocyanic acid, (2-benzothiazolylthio) methyl ester (TCMTB) is an oil with a pungent odor. It is used as wood preservative, marine biocide, fungicide, and as a preservative in paint. It is also widely employed in leather production. HUMAN EXPOSURE AND TOXICITY: Symptoms consistently elevated in TCMTB mills included dry skin around the eyes, blood-stained mucus from the nose, nose bleed, peeling skin, burning or itching skin, and skin redness or rash. TCMTB has been classified by EPA as group C, possible human carcinogen, based on animal studies. ANIMAL STUDIES: TCMTB was of moderate to low acute oral toxicity in rats and of low dermal toxicity in rabbits. Following subchronic oral exposures to rodents, TCMTB caused increased incidence of mild to severe stomach lesions characterized by inflammation, hyperplasia, necrosis, and ulceration. In a 21-day rat dermal toxicity study, TCMTB produced dose-dependant dermal irritation in all dose groups beginning on treatment days 3-4, which progressed to eschar formation. Rats in the mid and high dose group had ulcers, hemorrhages and chronic dermatitis. Decreased body weight gain, food consumption, and hematological (changes in hemoglobin, hematocrit, and segmented neutrophils) and clinical chemistry changes (blood urea nitrogen, glucose, globulins, and elevated serum aspartate aminotransferase (AST) were also noted. However, the clinical chemistry changes did not correspond to any treatment-related findings in the liver or kidney. In a chronic rat toxicity/carcinogenicity study, no adverse effects were noted at the highest dose tested of 20 mg/kg/day. However, there was a statistically significant increase in the incidence of testicular interstitial cell adenomas in males of mid- and high-dose levels that had a highly significant positive dose-related trend. Treatment was also associated with a possible increased incidence of thyroid C-cell adenomas in females of the mid- and high-dose levels, which had a highly significant positive dose-related trend, but did not attain a statistically significant level in the pairwise comparison with concurrent controls. TCMTB was found to be negative for mutagenicity in the gene mutation assay with bacteria and did not cause an increase in unscheduled DNA synthesis (UDS) in the rat hepatocytes assay. TCMTB was also found to be negative for chromosomal aberrations in the in vivo micronucleus assay in mice. Therefore, TCMTB is not mutagenic or genotoxic. ECOTOXICITY STUDIES: TCMTB was evaluated in three species of juvenile salmonids (Oncorhynchus kisutch, O. tshawytscha and O. mykiss). TCMTB was found to have both a concentration- and time-dependent effect on gill histology with damage apparent at concns as low as 6 ug/L. The relationship between the inhibitory effect on swimming speed and the observed gill damage was examined. These reductions in swimming speed may represent a limitation in gill oxygen transfer capacity resulting from TCMTB-induced alteration of gill structure.
Organic nitriles decompose into cyanide ions both in vivo and in vitro. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (L97)
/AQUATIC SPECIES/ The toxicity of the wood preservative agent 2-(thiocyanomethylthio)benzothiazole (TCMTB) was evaluated in three species of juvenile salmonids (Oncorhynchus kisutch, O. tshawytscha and O. mykiss). Gill tissues were examined for quantitative structural changes after a 96-hr LC50 acute test. TCMTB was found to have both a concentration and time dependent effect on gill histology with damage apparent at concentrations as low as 6 ug/L. The residual effect on swimming performance of a 12 to 48 hr sublethal TCMTB exposure was also examined. Concentration dependent reductions in swimming speed were observed with thresholds of 5 to 10 ug/L. The inhibitory effect on swimming performance was also found to be intensified by an increase in exposure duration. The relationship between the inhibitory effect on swimming speed and the observed gill damage was examined. These reductions in swimming speed may represent a limitation in gill oxygen transfer capacity resulting from TCMTB-induced alteration of gill structure.
Cough.
Dry skin. Redness. Roughness. Burning sensation.
Redness. Pain. Severe deep burns.
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 June 27, 2014: http://actor.epa.gov/dashboard/]
A previously unknown pollutant in river water was identified to be 2-mercaptobenzothiazole (2-MBT) by interpretation and simulation of its GC/LRMS spectrum. Further GC/HRMS measurement of the isotope composition of the molecular ion verified this structure. 2-MBT is a well-known agent for corrosion inhibition and a stable metabolite of several other benzothiazoles. The present 2-MBT trace was most probably a metabolite of the wood preservative TCMTB which leaked from an upstream sawmill. The metabolite had been detected earlier in urine of the sawmill workers, but now was identified in the recipient water environment for the first time.
A method for biological monitoring of urinary 2-(thiocyanomethylthio)benzothiazole (TCMTB), a wood preservative and an industrial chemical, was developed. Urine samples of sawmill workers exposed to TCMTB were collected after their work shifts for exposure assessment. TCMTB could not be detected in the urine samples of exposed workers. Most concentrations of 2-MBT were below the limit of the detection, 0.12 mumol/L, the concentrations were 0.12-0.15 mumol/L only in few cases. The determination of 2-MBT /(2-mercaptobenzothiazole)/ in urine, when a sample is taken immediately after a work shift, is a suitable indicator of workers' exposure to TCMTB.
Tolerances are established for residues of the fungicide 2-(thiocyanomethylthio)benzothiazole in or on the following food commodities:[Table#5974]
The Agency has completed its assessment of the dietary, occupational, drinking water, and ecological risks associated with the use of pesticide products containing the active ingredient TCMTB. Based on a review of these data and on public comments on the Agency's assessments for the active ingredient TCMTB, the Agency has sufficient information on the human health and ecological effects of TCMTB to make decisions as part of the tolerance reassessment process under FFDCA and reregistration process under FIFRA, as amended by FQPA. The Agency has determined that TCMTB-containing products are eligible for reregistration provided that: (i) current data gaps and confirmatory data needs are addressed; (ii) the risk mitigation measure outlined in this document is adopted; and (iii) label amendments are made to reflect this measure. Label changes are described in Section V. Appendix A summarizes the uses of TCMTB that are eligible for reregistration. ... Based on its evaluation of TCMTB, the Agency has determined that TCMTB products, unless labeled and used as specified in this document, would present risks inconsistent with FIFRA. Accordingly, should a registrant fail to implement the risk mitigation measure identified in this document, the Agency may take regulatory action to address the risk concerns from the use of TCMTB. If all changes outlined in this document are incorporated into the product labels, then all current risks for TCMTB will be substantially mitigated for the purposes of this determination. Once an Endangered Species assessment is completed, further changes to these registrations may be necessary.
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 safeey 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-(Thiocyanomethylthio)benzothiazole is found on List B. Case No: 2625; Pesticide type: fungicide, antimicrobial; Case Status: PreRED - OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the RED document.; Active ingredient (AI): 2-(Thiocyanomethylthio)benzothiazole; Data Call-in (DCI) Date(s): 06/30/91, 10/13/95; AI Status: The producers of the pesticide have made commitments to conduct the studies and pay the fees required for reregistration, and are meeting those commitments in a timely manner.
Antimicrobial agent used as a substitute for chlorophenols in industrial applications.
Wood preservative, marine biocide, fungicide.
TCMTB was first registered as an active ingredient by the United States Environmental Protection Agency (EPA) on January 21, 1980. ... TCMTB products are used in commercial/institutional premises and residential and public access areas. As an antimicrobial pesticide, TCMTB is used largely as a materials preservative (e.g., leather products and hides, pulp/paper products, latex, wallpaper, paints, carpets). TCMTB is a slimicide ... for controlling bacteria, fungi and yeasts, which cause deterioration of paper and paperboard products. TCMTB is also used as a fungicide for commercial and on-farm seed treatment.
Production: formaldehyde + sodium thiocyanate + 2-mercaptobenzothiazole (chloromethylation/dehydrochlorination)
162.4 g of chloromethyl thiocyanate was added to a soln of 258.5 g 2-mercaptobenzothiazole and 102.8 g sodium ethoxide in 400 mL absolute ethyl alcohol which was cooled to <40 °C while the reaction took place. The mixture was kept at 35-40 °C overnight and 15 days at room temp and filtered. The filtrate plus methylene chloride extractions from the filter cake gave 118 g of 2-(thiocyanomethyl)-benzothiazole. This was combined with 242.1 g of product recovered from the alcohol phase. The product could not be distilled without decomposition but was identified by a strong infrared band at 4.62 microns..
The National Pesticide Information Retrieval System (NPIRS) identifies 3 companies with active labels for products containing the chemical 2-(thiocyanomethylthio)benzothiazole. To view the complete list of companies, product names and percent 2-(thiocyanomethylthio)benzothiazole in formulated products click the following url and enter the CAS Registry number in the Active Ingredient field.
TCMTB (Buckman Laboratories, Inc.): Active ingredient: 2-(thiocyanomethylthio)benzothiazole 80.0%.
Busan 72 (Buckman Laboratories, Inc.): Active ingredient: 2-(thiocyanomethylthio)benzothiazole 60.0%.
Busan 30 (Buckman Laboratories, Inc.): Active ingredient: 2-(thiocyanomethylthio)benzothiazole 30.0%.
For more Formulations/Preparations (Complete) data for 2-(Thiocyanomethylthio)benzothiazole (28 total), please visit the HSDB record page.
Organic booster biocides were recently introduced as alternatives to organotin compounds in antifouling products, after restrictions imposed on the use of tributyltin (TBT) in 1987. Replacement products are generally based on copper metal oxides and organic biocides. This ban has led to an increase in alternative coating products containing the above biocides. The most commonly used biocides in antifouling paints are: Irgarol 1051, diuron, Sea-nine 211, dichlofluanid, chlorothalonil, zinc pyrithione, TCMS (2,3,3,6-tetrachloro-4-methylsulfonyl) pyridine, TCMTB [2-(thiocyanomethylthio) benzothiazole], and zineb. Since 1993, several studies have demonstrated the presence of these biocides in European coastal environment as a result of their increased use. More recently, the presence of these biocides was also revealed in waters from Japan, United States, Singapore, Australia and Bermuda. This paper reviews the currently available data on the occurrence of these biocides in the aquatic environment. Some data dealing with the environmental fate, partitioning, behaviour and risk assessment of antifouling paint booster biocides are also reported in order to discuss the detected levels of contamination.
용도2-(Thiocyanatomethylthio)benzothiazole is an antimicrobial agent used as a substitute for chlorophenols in industrial applications.