21564-17-0

Basic information

• Product Name: 2-(Thiocyanatomethylthio)benzothiazole
• Synonyms: (1,3-Benzothiazol-2-ylsulfanyl)methyl thiocyanate;(2-benzothiazolylthio)methylthiocyanate[qr];2-(thiocyanomethylthio)benzothiazole,60%;2-(thiocyanomethylthio)benzothiazole[qr];2-thiocyanomethylthiobenzothiazole,80%;2-tiocianometiltiobenzotiazolo,80%;2-tiocianometiltiobenzotiazolo[qr];ai3-29396-x(usda)[qr]
• CAS NO: 21564-17-0
• Molecular Formula: C₉H₆N₂S₃
• Molecular Weight: 238.35
• EINECS: 244-445-0
• Product Categories: Organics;Biocide;BenzothiazolesAlphabetic;Fungicides;Pesticides;TA - TE;Aromatics;Heterocycles;Sulfur & Selenium Compounds;2-(Thiocyanomethylthio) benzothiazole
• Mol File: 21564-17-0.mol
• Article Data: 11

Chemical Properties

• Melting Point: <-10 °C
• Boiling Point: 405.6 °C at 760 mmHg
• Flash Point: (open cup): 66°C
• Appearance: Brown-red liquid
• Density: d25 1.05 (c = 0.30)
• Vapor Pressure: 8.65E-07mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: 0-6°C
• PKA: -0.09±0.10(Predicted)
• CAS DataBase Reference: 2-(Thiocyanatomethylthio)benzothiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(Thiocyanatomethylthio)benzothiazole(21564-17-0)
• EPA Substance Registry System: 2-(Thiocyanatomethylthio)benzothiazole(21564-17-0)

Safety Data

• Hazard Codes: T+,N,Xn
• Statements: 22-26-36/38-43-50/53-36/37/38
• Safety Statements: 28-36/37-38-45-60-61-36-26
• RTECS: XK8150900
• Hazardous Substances Data: 21564-17-0(Hazardous Substances Data)

Usage

Description

(Benzothiazol-2-ylthio)methyl thiocyanate?(TCMTB) is a?chemical compound?classified as a?benzothiazole. 2-(thiocyanomethylthio)benzothiazole is a a soil and seed treatment used to control various fungal and bacterial infections. It is moderately soluble in water, has a low volatility and is not expected to be persistent in soil systems. It is not eexpected to leach to groundwater. It has a pungent odour, is highly toxic to most aquatic species and moderately toxic to birds. 2-(thiocyanomethylthio)benzothiazole is highly toxic to humans via the oral route and is a recognised irritant.

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. The degradation products are?2-mercaptobenzothiazole?(2-MBT) and?2-benzothiazolesulfonic acid.

Approval

TCMTB is not an authorized plant protection product in the European Union.In Germany, Austria and Switzerland, no plant protection products containing this active substance are authorized.

Chemical Properties

Brown Oil

Physical properties

It is a viscous reddish liquid and is insoluble in vater， but soluble in organic solvents such as acetone,dimethylformamide,cyclohexanone， benzene and xylene. It has a specific gravityof 1.38,a boiling point greater than 120℃ and a vapour pressure of about 0.05 torr. The supplier normally dissolves TCMTB in a mixture of organic solvents to form a concentrate. Emulsifiers or surfactants may be added to the concentrate to improve the stability of emulsions formed when the concentrate is diluted withwater. TCMTB is sold commercially as 80% technical material under thetrade name "TCMTB" by Buckman Laboratories，Which is the soleanufacturer of the material.The patented preparationinvolves a reaction of 2-mercaptobenzothiazole and chloromethylthiocyanate,but confidential data obtained from Buckman Laboratories indicates another preparative method may now be used.

History

The commercial use of TCMTB apparently had its origins in with Buckman Laboratories，Inc., of Memphis，Tennessee. In thelate 1940's this company became involved in the search for solutions to the problem of breaks in paper on high speed paperachines due to the formation of microbiological slime.rhecompany first developed the microbiocide BSM-11,a product containing mercuric acetate and trichlorophenol, which seemed tof ind acceptance in the paper making industry. However, in view of the potentiaL for adverse health and environmental impacts from the use of mercury compounds，BuckmanLaboratories developed a 1ine of organosulphur compounds whichalso proved to be effective slime control agents."Alone， or inconjunction with other active ingredients，TCMTB is now found in avariety of Buckman products.

Uses

Different sources of media describe the Uses of 21564-17-0 differently. You can refer to the following data:
1. 2-(Thiocyanatomethylthio)benzothiazole is an antimicrobial agent used as a substitute for chlorophenols in industrial applications.
2. Wood preservative, marine biocide, fungicide.

Toxicology

There are few published studies on the toxicity of TCMTB or Busan1030. Confidential information received from Buckman Laboratoriesindicates that most of the toxicity studies on TCMTB and Busan 1030 have been carried out by private laboratories and that this data vas submitted to government agencies as part of the pesticideregistration process. "Unfortunately, this data is not available from Agriculture Canada, but has been requested by the company from the B.C. Ministry of Environment and Parks' wasteManagement Branch .

InChI:InChI=1/C9H6N2S3/c10-5-12-6-13-9-11-7-3-1-2-4-8(7)14-9/h1-4H,6H2

Upstream product

• 149-30-4 2-Mercaptobenzothiazole 
• 615-22-5 2-methylmercaptobenzothiazole 
• 3507-54-8 2-(methylsulfinyl)benzothiazole 
• 28908-00-1 (2-chloromethylthio)benzothiazole 
• 1147550-11-5 ammonium thiocyanate 
• 540-72-7 sodium thiocyanide 
• 3268-79-9 chloromethyl thiocyanate 

Relevant articles and documents

Synergistic biocide composition

A biocide composition is provided as an addition to substances that can be infected by harmful microorganisms, in which the biocide composition has at least two active biocidal substances, one of which is 2-methylisothiazolin-3-one. The composition is characterized in that it contains 1,2-benzisothiazolin-3-one, compositions containing 5-chloro-2-methylisothiazolin-3-one being excluded. In comparison with its individual components, the composition of the invention has a synergistic biocidal activity.

Wood preservatives

Wood preservatives having biocidal properties which include quaternary ammonium compounds of general formula (I): wherein R1 is a C8-18-alkyl group or an optionally substituted benzyl group, R2 is a C8-18-alkyl group, R3 is a C1-4-alkyl group or a group of the formula —[CH2—CH2—O]n—H, R4 is a C1-4-alkyl group, n is a number from 0.5 to 8, preferably from 1 to 5, and A?is the anion of an organic carboxylic acid which contains 2 to 12 C atoms and carries at least one hydroxyl, amino or sulfonic acid group. The wood preservatives also penetrate deeply into the wood without the use of pressure, and have only a mild corrosive action on metals. Furthermore, a process for treating timbers with these compositions, concentrates for the preparation thereof, the use of new and known quaternary ammonium compounds in wood preservatives and new quaternary ammonium compounds and their use as biocides.

Soluble polymer based matrix for chemically active water insoluble components

This invention relates to a water soluble matrix composition comprising an anionic surfactant, a C6 to C18 alkyl pyrrolidone, urea and a water insoluble copolymer of vinyl pyrrolidone with not more than 50 wt. % of a comonomer selected from the group of an α-olefin, vinyl acetate, an acrylic or methacrylic acid ester and methacrylamide as a free flowing particulate solid which matrix is suitably mixed with a water insoluble, chemically active component, such as an agrochemical, to provide a clear sprayable film forming emulsion, such as a non-leachable film on a plant or other substrate surface. The invention also relates to the method of preparing the matrix and to the incorporation of an agrochemical concentrate and plant spray composition.