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

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

Uses

Used in Industrial Applications:
2-(Thiocyanatomethylthio)benzothiazole is used as an antimicrobial agent for substituting chlorophenols in various industrial applications.
Used in Wood Preservation:
In the wood preservation industry, 2-(Thiocyanatomethylthio)benzothiazole is used as a wood preservative to protect against fungal and bacterial infections.
Used as a Marine Biocide:
2-(Thiocyanatomethylthio)benzothiazole is utilized as a marine biocide to prevent the growth of harmful organisms on submerged surfaces.
Used as a Fungicide:
In agriculture, 2-(Thiocyanatomethylthio)benzothiazole is used as a fungicide to control various fungal infections on crops.
Used in Soil and Seed Treatment:
2-(Thiocyanatomethylthio)benzothiazole is employed as a soil and seed treatment to control various fungal and bacterial infections. It is moderately soluble in water, has low volatility, and is not expected to be persistent in soil systems. It is also not expected to leach to groundwater.
Production and Commercial Availability:
TCMTB is sold commercially as 80% technical material under the trade name "TCMTB" by Buckman Laboratories, which is the sole manufacturer of the material. The patented preparation involves a reaction of 2-mercaptobenzothiazole and chloromethylthiocyanate, but confidential data obtained from Buckman Laboratories indicates another preparative method may now be used. 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 with water.

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.

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.

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

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

Protective agents for wood

Solvent-free coating materials and treating agents used as water-based wood or material protective agents containing emulsifiable binding agents, quaternary ammonium compounds and optional additional active agents. The wood or material protective agents are non-flammable and enable a uniform distribution of the binding agent and the quaternary ammonium compounds in the substrates. As a result, the quaternary ammonium compounds function as a dissolving mediator for the binding agents which are dispersed in water without opacifying effects and are used as a biocide. The agents can additionally absorb water-insoluble organic biocides without impairing the homogeneity or stability of the formulation of the homogeneity of the distribution in the substrate.

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.

Convenient synthesis of chloromethyl thioaromatics

The work presents a simple procedure for the synthesis of the title compounds derived from heterocyclic thiols and a bifunctional alkylating agent in the presence of anion exchange resin.

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.

Convenient synthesis of 2-(thiocyanomethylthio)benzothiazole

A highly efficient and general route has been developed for 2-(thiocyanomethylthio)benzothiazole 3 which is synthesised by reacting a chlorinating agent with 2-mercaptobenzothiazole 1 followed by reactions involving 2-(methylthio)benzothiazole 1b and 2-(methylsulfinyl)benzothiazole 2 under various conditions.

Process for the production of 2-thiocyanomethylthiobenzothiazole

A process for the manufacture of 2-thiocyanomethylthiobenzothiazole. 2-Chloromethylthiobenzothiazole is reacted, in the presence of at least one glycol ether as a solvent for the reaction, with either an alkali metal or an ammonium thiocyanate at a temperature and for a time sufficient to produce the 2-thiocyanomethylthiobenzothiazole.

Organosilyl compounds and their use as fungicides

Organosilyl compounds of the general formula I STR1 where R1, R2 and R3 are alkyl, substituted alkyl, alkenyl, alkynyl, cycloalkyl, phenyl or substituted aryl, R4 and R5 are alkyl or hydrogen and Y is CH2, oxygen, nitrogen or alkyl-substituted nitrogen, their salts and fungicides containing these compounds.

4-Nitro-2-trichloromethylphenylsulfenamides

New 4-nitro-2-trichloromethylphenylsulfenamides having a fungicidal and bactericidal action, processes for their manufacture, fungicides containing these compounds as active ingredients, and a process for combating fungi with these compounds.

Thiolphosphoric acid-S-4-nitro-2-trichloromethylphenyl esters as fungicides

New thiolphosphoric acid-S-4-nitro-2-trichloromethylphenyl esters of the formula STR1 where X denotes oxygen or sulfur, and R1 and R2 are identical or different and each denotes a substituted or unsubstituted aliphatic radical of 1 to 18 carbon atoms or a substituted or unsubstituted alicyclic radical of 5 to 18 carbon atoms, processes for their manufacture, fungicides containing these compounds as active ingredients, their manufacture, and processes for combating fungi with these novel compounds.