(Benzothiazol-2-ylthio)methyl thiocyanate (TCMTB) is a chemical compound classified as a benzothiazole.
benzothiazole.svg)
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| Names | |
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| Preferred IUPAC name
[(1,3-benzothiazol-2-yl)sulfanyl]methyl thiocyanate | |
Other names
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| Identifiers | |
3D model (JSmol)
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| ChEMBL | |
| ECHA InfoCard | 100.040.390 |
| EC Number |
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PubChem CID
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| RTECS number |
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C9H6N2S3 | |
| Molar mass | 238.34 g·mol−1 |
| Appearance | Red to brown liquid with pungent odor [2] |
| Density | 1.05 |
| Melting point | −10 °C (14 °F; 263 K)[2] |
| Boiling point | 191 °C (376 °F; 464 K) |
| Very slightly soluble (0.125 g/L at 24 °C)[2] | |
| log P | 3.23 |
| Vapor pressure | 9.0×10−6 mmHg |
| Hazards | |
| GHS labelling: | |
   
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| Danger | |
| H302, H312, H315, H317, H319, H330, H410 | |
| P260, P261, P264, P270, P271, P272, P273, P280, P284, P301+P312, P302+P352, P304+P340, P305+P351+P338, P310, P312, P320, P321, P322, P330, P332+P313, P333+P313, P337+P313, P362, P363, P391, P403+P233, P405, P501 | |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose)
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679 mg/kg (rat, oral)[2] 200 mg/kg (rabbit, dermal)[2] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Properties
editTCMTB is an oily, flammable, red to brown liquid with a pungent odor that is very slightly soluble in water. It decomposes on heating producing hydrogen cyanide, sulfur oxides, and nitrogen oxides.[2] The degradation products are 2-mercaptobenzothiazole (2-MBT) and 2-benzothiazolesulfonic acid.[3]
Uses
editTCMTB is used as wideband microbicide, paint fungicide, and paint gallicide.[2] The active substance approved in 1980 in the United States.[3] It is used, for example, in leather preservation,[4] for the protection of paper products, in wood preservatives, and against germs in industrial water.[3]
In the US, TCMTB is used as a fungicide for seed dressing in cereals, safflower, cotton and sugar beet.
It is also used when dealing with fungal problems when extracting hydrocarbons via fracking.[5]
Approval
editTCMTB is not an authorized plant protection product in the European Union.[6] In Germany, Austria and Switzerland, no plant protection products containing this active substance are authorized.[7]
TCMTB contributes to health problems in tannery workers as it is a potential carcinogen, and is a hepatotoxin. It is also a skin sensitizer, and may cause contact dermatitis in those exposed to the poisonous compound. [8] Hence, it is mainly used in developing countries.
References
edit- ^ Thomas Swan: Coating Additives & Leather Fungicides
- ^ a b c d e f g Record of CAS RN 21564-17-0 in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 3. August 2012.
- ^ a b c EPA: Reregistration Eligibility Decision for 2- (thiocyanomethylthio) benzothiazoles (TCMTB) (PDF; 2.7 MB), August 2006.
- ^ Engin Bagda (2000). Biocides in Building Coatings. expert publisher. p. 59. ISBN 3-81691861-1.
- ^ Levant, Ezra (2014). Groundswell: The Case for Fracking. McClelland & Stewart. p. 192.
- ^ Commission Regulation (EC) No 2076/2002 of 20 November 2002. EUR-Lex Act 319, pp. 3–11 (PDF) "On the extension of the deadline laid down in Article 8 (2) of Council Directive 91/414 / EEC and on the non-inclusion of certain active substances in Annex I to this Directive and the withdrawal of the Authorizations for plant protection products containing these active substances"
- ^ PSM-del, EU- 2- (dithiocyanomethylthio) -benzothiazole | CH = DB | A = DB | D = DB | 8 March 2016
- ^ "TCMTB - Hazardous Agents | Haz-Map".