TCMTB

TCMTB
Names
	Preferred IUPAC name [(1,3-benzothiazol-2-yl)sulfanyl]methyl thiocyanate
	Other names 2-(Thiocyanomethylthio)benzothiazole; Thiocyanic acid 2-(benzothiazolethio) methyl ester; Casacide;
Identifiers
CAS Number	21564-17-0;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL1903976;
ChemSpider	28480;
ECHA InfoCard	100.040.390
EC Number	244-445-0;
PubChem CID	30692;
RTECS number	XK8150900;
UNII	5GE166YVQV;
CompTox Dashboard (EPA)	DTXSID6032647 ;
	InChI 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;
	SMILES C1=CC=C2C(=C1)N=C(S2)SCSC#N;
Properties
Chemical formula	C9H6N2S3
Molar mass	238.34 g·mol−1
Appearance	Red to brown liquid with pungent odor
Density	1.05
Melting point	−10 °C (14 °F; 263 K)
Boiling point	191 °C (376 °F; 464 K)
Solubility in water	Very slightly soluble (0.125 g/L at 24 °C)
log P	3.23
Vapor pressure	9.0×10−6 mmHg
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H302, H312, H315, H317, H319, H330, H410
Precautionary statements	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)	679 mg/kg (rat, oral); 200 mg/kg (rabbit, dermal)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

(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

^ 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".

[1] Thomas Swan: Coating Additives & Leather Fungicides

[GESTIS-2] ^ ^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.

[EPA-3] EPA: Reregistration Eligibility Decision for 2- (thiocyanomethylthio) benzothiazoles (TCMTB) (PDF; 2.7 MB), August 2006.

[Engin_Bagda-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"

[PSM-7] PSM-del, EU- 2- (dithiocyanomethylthio) -benzothiazole | CH = DB | A = DB | D = DB | 8 March 2016

[8] "TCMTB - Hazardous Agents | Haz-Map".

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