TCMTB

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

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[1]
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 [2]
Density	1.05
Melting point	−10 °C (14 °F; 263 K)[2]
Boiling point	191 °C (376 °F; 464 K)
Solubility in water	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:
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)[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). Infobox references

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.