Article · Wikipedia archive · Last revised Jul 7, 2026

TCMTB

(Benzothiazol-2-ylthio)methyl thiocyanate (TCMTB) is a chemical compound classified as a benzothiazole.

Last revised
Jul 7, 2026
Read time
≈ 2 min
Length
550 w
Citations
16
Source
Wikipedia ↗
TCMTB
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Names
Preferred IUPAC name
[(1,3-benzothiazol-2-yl)sulfanyl]methyl thiocyanate
Other names
  • 2-(Thiocyanomethylthio)benzothiazole
  • Thiocyanic acid 2-(benzothiazolethio) methyl ester
  • Casacide1
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.040.390
EC Number
  • 244-445-0
RTECS number
  • XK8150900
UNII
  • InChI=1S/C9H6N2S3/c10-5-12-6-13-9-11-7-3-1-2-4-8(7)14-9/h1-4H,6H2
    Key: TUBQDCKAWGHZPF-UHFFFAOYSA-N
  • C1=CC=C2C(=C1)N=C(S2)SCSC#N
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:
GHS06: ToxicGHS08: Health hazardGHS09: Environmental hazardGHS07: Exclamation mark
Danger
H302, H312, H315, H317, H319, H330, H410
P260, P264, P270, P271, P272, P273, P280, P284, P301+P312, P302+P352, P304+P340, P305+P351+P338, P310, P312, P320, P321, P330, P332+P313, P333+P313, P337+P313, P362, P363, P391, P403+P233, P405, P501
Lethal dose or concentration (LD, LC):
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).

(Benzothiazol-2-ylthio)methyl thiocyanate (TCMTB) is a chemical compound classified as a benzothiazole.

Properties

TCMTB 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

TCMTB 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

TCMTB 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

References

  1. Thomas Swan: Coating Additives & Leather Fungicides
  2. 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.
  3. EPA: Reregistration Eligibility Decision for 2- (thiocyanomethylthio) benzothiazoles (TCMTB) (PDF; 2.7 MB), August 2006.
  4. Engin Bagda (2000). Biocides in Building Coatings. expert publisher. p. 59. ISBN 3-81691861-1.
  5. Levant, Ezra (2014). Groundswell: The Case for Fracking. McClelland & Stewart. p. 192.
  6. 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"
  7. PSM-del, EU- 2- (dithiocyanomethylthio) -benzothiazole | CH = DB | A = DB | D = DB | 8 March 2016
  8. "TCMTB - Hazardous Agents | Haz-Map".