2-(thiocyanomethylthio)benzothiazole

2-(thiocyanomethylthio)benzothiazole	Last updated: 13/10/2023
(Also known as: TCMTB; TCMB; alentisan; KVK 733059)

SUMMARY

2-(thiocyanomethylthio)benzothiazole is 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 expected 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 Class (HRAC MoA class)

Not applicable

Herbicide Resistance Class (WSSA MoA class)

Not applicable

Insecticide Resistance Class (IRAC MoA class)

Not applicable

Fungicide Resistance Class (FRAC MOA class)

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
Busan 72

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

at 24 °C

Moderate

Solubility - In organic solvents at 20 °C (mg l⁻¹)

Miscible

Ethanol

Miscible

Ethyl acetate

Melting point (°C)

Boiling point (°C)

191

Degradation point (°C)

Flashpoint (°C)

189

Octanol-water partition coefficient at pH 7, 20 °C

2.00 X 10⁰³

Calculated

Log P

3.3

High

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

1.4

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

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

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

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

K_d

Non-mobile

K_oc

4089

Notes and range

K_oc range 282 - 7896 mL g⁻¹

Freundlich

K_f

K_foc

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

Whole fish

Threshold for concern

CT₅₀ (days)

Not available

Known soil metabolites

Metabolite

Major/Minor fraction

$Click here for further information on Major/Minor fraction$

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

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

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

Oncorhynchus mykiss

High

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.00034

Oncorhynchus mykiss 60 day

High

Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)

0.0153

Ceriodaphnia dubia

High

Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)

0.00089

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

Pseudokirchneriella subcapitata

Moderate

Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)

Mesocosm study data

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

Rat

Moderate

Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)

10000

Rabbit

Mammals - Inhalation LC₅₀ (mg l⁻¹)

0.0671

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

; ; ; ;

No data found

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

Probably liver and kidney toxicant
May damage eyes
US EPA - possible human carcinogen

Handling issues

Property

Value and interpretation

General

Corrosive
Combustable

CLP classification 2013

Health: H302, H315, H319, H330
Environment: H400, H410

WHO Classification

Not classified: Obsolete (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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Record last updated:	13/10/2023
Contact:	aeru@herts.ac.uk
Please cite as:	Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242