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2-(thiocyanomethylthio)benzothiazole
(Also known as: TCMTB; TCMB; alentisan; KVK 733059)
SUMMARY
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.
Data alerts

The following alerts are based on the data in the tables below. An absence of an alert does not imply the substance has no implications for human health, biodiversity or the environment but just that we do not have the data to form a judgement.

Environmental fate Ecotoxicity Human health
Environmental fate
Moderate alert:
Potential for particle bound transport: Medium
Warning:
Significant data are missing
Ecotoxicity
High alert:
Fish acute ecotoxicity: High; Fish chronic ecotoxicity: High; Daphnia acute ecotoxicity: High; Daphnia chronic ecotoxicity: High
Human health
Moderate alert:
Mammals acute toxicity: Moderate; Possible Carcinogen
GENERAL INFORMATION
Description
Used as a soil and seed treatment against various diseases. Also used as a marine biocide, and as a wood and leather preservative.
Example pests controlled
Mildews; Moulds; Bacterial blight; Bacterial slime; Basal rot; Brown rot; Damping off; Kernal smut; Bunt
Example applications
Cereals including barley, wheat, oats; Ornamentals; Cotton, Rice; Legumes; Sorghum; Sugar beet
Efficacy & activity
-
Availability status
Current
Introduction & key dates
1980, USA
UK regulatory status
UK COPR regulatory status
Not approved
Date COPR inclusion expires
Expired
UK LERAP status
No UK approval for use
EC Regulation 1107/2009 (repealing 91/414)
EC Regulation 1107/2009 status
Not approved
Dossier rapporteur/co-rapporteur
Not applicable
Date EC 1107/2009 inclusion expires
Expired
EU Candidate for substitution (CfS)
Not applicable
Listed in EU database
Yes
Approved for use (✓) under EC 1107/2009 in the following EU Member States
ATAustria
BEBelgium
BGBulgaria
CYCyprus
CZCzech Republic
DEGermany
DKDenmark
EEEstonia
ELGreece
                 
ESSpain
FIFinland
FRFrance
HRCroatia
HUHungary
IEIreland
ITItaly
LTLithuania
LULuxembourg
                 
LVLatvia
MTMalta
NLNetherlands
PLPoland
PTPortugal
RORomania
SESweden
SISlovenia
SKSlovakia
                 
Approved for use (✓) under EC 1107/2009 by Mutual Recognition of Authorisation and/or national regulations in the following EEA countries
ISIceland
NONorway
                 
Additional information
Also used in
USA
Chemical structure
Isomerism
None
Chemical formula
C₉H₆N₂S₃
Canonical SMILES
C1=CC=C2C(=C1)N=C(S2)SCSC#N
Isomeric SMILES
-
International Chemical Identifier key (InChIKey)
TUBQDCKAWGHZPF-UHFFFAOYSA-N
International Chemical Identifier (InChI)
InChI=1S/C9H6N2S3/c10-5-12-6-13-9-11-7-3-1-2-4-8(7)14-9/h1-4H,6H2
2D structure diagram/image available?
Yes
General status
Pesticide type
Fungicide, Microbiocide, Other substance
Other constituent type
Wood preservative
Substance groups
Mercaptobenzothiazole fungicide; Mercaptobenzothiazole biocide
Minimum active substance purity
-
Known relevant impurities
-
Substance origin
Synthetic
Mode of action
Complex - reacts with the nucleophilic cell entities which causes the antimicrobial activity. Also known to inhibit flavoenzymes in the tricarboxylic acid cycle.
CAS RN
21564-17-0
EC number
244-445-0
CIPAC number
None allocated
US EPA chemical code
035603
PubChem CID
30692
CLP index number
613-119-00-3
Molecular mass
238.36
PIN (Preferred Identification Name)
-
IUPAC name
2-(thiocyanatomethylthio)-1,3-benzothiazole
CAS name
(2-benzothiazolylthio)methyl thiocyanate
Other status information
-
Relevant Environmental Water Quality Standards
-
Herbicide Resistance Classification (HRAC)
Not applicable
Herbicide Resistance Classification (WSSA)
Not applicable
Insecticide Resistance Classification (IRAC)
Not applicable
Fungicide Resistance Classification (FRAC)
Not known
Examples of recorded resistance
-
Physical state
Dark orange liquid
Formulations
Property
Value
Example manufacturers & suppliers of products using this active now or historically
-
Example products using this active
  • Busan 30
  • Busan 44
  • Superdavloxan
Formulation and application details
Usually supplied as an emulsifiable liquid, ready-to-use liquids and wettable powders
ENVIRONMENTAL FATE
Property
Value
Source; quality score; and other information
Interpretation
Solubility - In water at 20 °C (mg l⁻¹)
125
V4 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
4 = Verified data
at 24 °C		 Moderate
Solubility - In organic solvents at 20 °C (mg l⁻¹)
Miscible
Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source
Ethanol		 -
Miscible
Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source
Ethyl acetate		 -
Melting point (°C)
- - -
Boiling point (°C)
191
F3 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
3 = Unverified data of known source
 -
Degradation point (°C)
60 - -
Flashpoint (°C)
189
Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source
 -
Octanol-water partition coefficient at pH 7, 20 °C
P
2.00 X 1003 Calculated -
Log P
3.3
V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
3 = Unverified data of known source
 High
Fat solubility of residues
Solubility
- - -
Data type
- - -
Density (g ml⁻¹)
1.4
Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source
 -
Dissociation constant pKa) at 25 °C
- - -
-
Vapour pressure at 20 °C (mPa)
- - -
Henry's law constant at 25 °C (Pa m³ mol⁻¹)
6.58 X 10-07
V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
3 = Unverified data of known source
 Non-volatile
Maximum UV-vis absorption L mol⁻¹ cm⁻¹
- - -
Surface tension (mN m⁻¹)
- - -
Degradation
Property
Value
Source; quality score; and other information
Interpretation
General biodegradability
-
Soil degradation (days) (aerobic)
DT₅₀ (typical)
1.4
F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
4 = Verified data
 Non-persistent
DT₅₀ (lab at 20 °C)
- - -
DT₅₀ (field)
- - -
DT₉₀ (lab at 20 °C)
- - -
DT₉₀ (field)
- - -
DT₅₀ modelling endpoint
- - -
Note
-
Dissipation rate RL₅₀ on plant matrix
Value
- - -
Note
-
Dissipation rate RL₅₀ on and in plant matrix
Value
- - -
Note
-
Aqueous photolysis DT₅₀ (days) at pH 7
Value
- - -
Note
-
Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7
Value
-
F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
4 = Verified data
 -
Note
Stable at pH 5, slow hydrolysis at pH 7, around 2 days at pH 9
Water-sediment DT₅₀ (days)
- - -
Water phase only DT₅₀ (days)
- - -
Soil adsorption and mobility
Property
Value
Source; quality score; and other information
Interpretation
Linear
Kd
-
R4 R = Peer reviewed scientific publications
4 = Verified data
 Non-mobile
Koc
4089
Notes and range
Koc range 282 - 7896 mL g⁻¹
Freundlich
Kf
- - -
Kfoc
-
1/n
-
Notes and range
-
pH sensitivity
-
Fate indices
Property
Value
Source; quality score; and other information
Interpretation
GUS leaching potential index
0.06 Calculated Low leachability
SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate
Value
2.07 X 10-04 Calculated -
Note
-
Potential for particle bound transport index
Medium Calculated -
Potential for loss via drain flow
Non-mobile Calculated -
Bio-concentration factor
BCF (l kg⁻¹)
230
P3 P = Other non-EU, UK or US Governments and Regulators
3 = Unverified data of known source
Whole fish		 Threshold for concern
CT₅₀ (days)
Not available -
Known soil metabolites
Metabolite
Major/Minor fraction
Estimated maximum occurrence fraction
Notes
2-mercaptobenzothiazole
Minor fraction - -
2-benzothiazolesulfonic acid
Minor fraction - -
Known groundwater metabolites
Metabolite
EC SANCO/221/2000 relevancy
ADI (mg kg⁻¹ bodyweight day⁻¹)
WHO drinking water guidance value (μg L⁻¹ day⁻¹)
2-mercaptobenzothiazole
Relevant - -
Other known metabolites

None
ECOTOXICOLOGY
Terrestrial ecotoxicology
Property
Value
Source; quality score; and other information
Interpretation
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
143
V4 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
4 = Verified data
Rat		 Moderate
Mammals - Short term dietary NOEL
(mg kg⁻¹)
- - -
(ppm diet)
- -
Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)
- - -
Birds - Acute LD₅₀ (mg kg⁻¹)
> 1310
V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
3 = Unverified data of known source
Anas platyrhynchos		 Moderate
Birds - Short term dietary (LC₅₀/LD₅₀)
- - -
Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)
- - -
Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)
- - -
Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)
- - -
Soil micro-organisms
- - -
Collembola
Acute LC₅₀ (mg kg⁻¹)
- - -
Chronic NOEC (mg kg⁻¹)
- - -
Non-target plants
- - -
- - -
Honeybees (Apis spp.)
Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
- - -
Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
- - -
Unknown mode acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
- - -
Chronic
- - -
Bumblebees (Bombus spp.)
Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
- - -
-
Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
- - -
-
Mason bees (Osmia spp.)
Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
- - -
Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
- - -
Other bee species (1)
Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)
- - -
Mode of exposure
-
Other bee species (2)
Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)
- - -
Mode of exposure
-
Beneficial insects (Ladybirds)
- - -
Beneficial insects (Lacewings)
- - -
Beneficial insects (Parasitic wasps)
- - -
Beneficial insects (Predatory mites)
- - -
Beneficial insects (Ground beetles)
- - -
Aquatic ecotoxicology
Property
Value
Source; quality score; and other information
Interpretation
Fish - Acute 96 hour LC₅₀ (mg l⁻¹)
0.0021
F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
4 = Verified data
Oncorhynchus mykiss		 High
Fish - Chronic 21 day NOEC (mg l⁻¹)
0.00034
P4 P = Other non-EU, UK or US Governments and Regulators
4 = Verified data
Oncorhynchus mykiss 60 day		 High
Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)
0.0153
F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
4 = Verified data
Ceriodaphnia dubia		 High
Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)
0.00089
P4 P = Other non-EU, UK or US Governments and Regulators
4 = Verified data
Daphnia magna		 High
Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)
- - -
Sediment dwelling organisms - Acute 96 hour LC₅₀ (mg l⁻¹)
- - -
Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l⁻¹)
- - -
Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg⁻¹)
- - -
Aquatic plants - Acute 7 day EC₅₀, biomass (mg l⁻¹)
- - -
Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)
0.43
F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
4 = Verified data
Pseudokirchneriella subcapitata		 Moderate
Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)
- - -
Mesocosm study data
NOEAEC mg l⁻¹
- - -
NOEAEC mg l⁻¹
- - -
HUMAN HEALTH AND PROTECTION
General
Property
Value
Source; quality score; and other information
Interpretation
Threshold of Toxicological Concern (Cramer Class)
High (class III) - -
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
143
V4 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
4 = Verified data
Rat		 Moderate
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)
10000
F3 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
3 = Unverified data of known source
Rabbit		 -
Mammals - Inhalation LC₅₀ (mg l⁻¹)
0.0671
P3 P = Other non-EU, UK or US Governments and Regulators
3 = Unverified data of known source
Rat		 -
Other Mammal toxicity endpoints
- - -
ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)
- - -
ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)
- - -
AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)
- - -
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)
- - -
Dermal penetration studies (%)
- - -
Dangerous Substances Directive 76/464
- - -
Exposure Routes
Public
-
Occupational
Can be absorbed into the body by inhalation of its aerosol and by ingestion
MRLs
European
EU MRL pesticide database 
Great Britain
GB MRL Register 
Notes
-
Drinking Water Standards
- - -
Drinking Water MAC (μg l⁻¹)
- - -
Mammalian dose elimination route and rate
- - -
Health issues
Specific human health issues
Carcinogen
Genotoxic
Endocrine disruptor
?Possibly, status not identified
A0 A = Chromosome aberration (EFSA database)
0 = No data
;
B0 B = DNA damage/repair (EFSA database)
0 = No data
;
C0 C = Gene mutation (EFSA database)
0 = No data
;
D0 D = Genome mutation (EFSA database)
0 = No data
;
E0 E = Unspecified genotoxicity type (miscellaneous data source)
0 = No data
 No data found
Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant
XNo, known not to cause a problem
XNo, known not to cause a problem
 No data found
Respiratory tract irritant Skin irritant Skin sensitiser
No data found
✓Yes, known to cause a problem
?Possibly, status not identified
Eye irritant Phototoxicant  
✓Yes, known to cause a problem
 No data found  
General human health issues
Probably liver and kidney toxicant
May damage eyes
Handling issues
Property
Value and interpretation
General
Corrosive
Combustable
CLP classification 2013
Health: H302, H315, H319, H330
EnvironmentL H400, H410
WHO Classification
Not classified: Obsolete
UN Number
-
Waste disposal & packaging
-
Shelf-life, storage, stability and reactivity
-
TRANSLATIONS
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Name
English
2-(thiocyanomethylthio)benzothiazole
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