Thiabendazole (Ref: MK 360)

Thiabendazole (Ref: MK 360)	Last updated: 26/06/2019
(Also known as: tiabendazole; TBZ; tebuzate)

GENERAL INFORMATION

Description

A mainly post-harvest fungicide used to control a wide range of diseases for fruit and other crops

Example pests controlled

Aspergillus; Botrytis; Cladosporium; Fusarium spp. including pod & stem blight, smut; damping-off, seedling blight, dwarf bunt, scab

Example applications

Fruit including apples, pears, citrus; Seed potatoes; Peas & chickpeas; Lentils; Cereals including wheat, barley, oats, rye, triticale, field corn; Popcorn; Sweetcorn

Efficacy & activity

Availability status

Current

Introduction & key dates

1961, discovered; 1964, first reported

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

30/03/2032

UK LERAP status

None (may vary with mixtures)

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Spain/Netherlands

Date EC 1107/2009 inclusion expires

30/03/2032

EU Candidate for substitution (CfS)

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
				✓	✓		✓

Also used in

Australia

Chemical structure

Isomerism

Chemical formula

C₁₀H₇N₃S

Canonical SMILES

C1=CC=C2C(=C1)NC(=N2)C3=CSC=N3

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

WJCNZQLZVWNLKY-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C10H7N3S/c1-2-4-8-7(3-1)12-10(13-8)9-5-14-6-11-9/h1-6H,(H,12,13)

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
thiabendazole	-

General status

Pesticide type

Fungicide, Veterinary substance

Substance group

Benzimidazole

Minimum active substance purity

985 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Systemic with curative and protective action. Acts by compromising the cytoskeleton through a selective interaction with ß-tubulin.

CAS RN

148-79-8

EC number

205-725-8

CIPAC number

323

US EPA chemical code

060101

PubChem CID

5430

Molecular mass

201.25

PIN (Preferred Identification Name)

2-(1,3-thiazol-4-yl)-1H-1,3-benzimidazole

IUPAC name

2-(thiazol-4-yl)benzimidazole

CAS name

2-(4-thiazolyl)-1H-benzimidazole

Other status information

Relevant Environmental Water Quality Standards

UK Environment Agency non-statutory standard for the protection of freshwater and saltwater aquatic life 5 µg l⁻¹ as annual average, 50 µg l⁻¹ as max acceptable conc

Herbicide Resistance Classification (HRAC)

Not applicable

Herbicide Resistance Classification (WSSA)

Not applicable

Insecticide Resistance Classification (IRAC)

Not applicable

Fungicide Resistance Classification (FRAC)

Examples of recorded resistance

Physical state

Colourless to yellow-white powder

Related substances & organisms

imazalil

thiram

Formulations

Property

Value

Example manufacturers & suppliers of products using this active now or historically

Hykeep
Storite
Tezate 220 SL
Tecto
Tobaz

Example products using this active

AgriGuard
Merial
Syngenta

Formulation and application details

Formulations include dry powders, soluble liquids and suspension concentrates

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

Low

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

n-Heptane

130

Xylene

8230

Methanol

2430

Acetone

Melting point (°C)

297

Boiling point (°C)

Degradation point (°C)

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

2.45 X 10⁰²

Calculated

Log P

2.39

Low

Bulk density (g ml⁻¹)

1.4

Dissociation constant pKa) at 25 °C

4.73

pKa(2) 12.00

Vapour pressure at 20 °C (mPa)

5.30 X 10^-04

Low volatility

Henry's law constant at 25 °C (Pa m³ mol⁻¹)

3.70 X 10^-06

Non-volatile

Maximum UV-vis absorption L mol⁻¹ cm⁻¹

Neutral: 234nm=15201, 242nm=15436, 299nm=23213, 312nm=16438
Acidic: 244nm=11554, 303nm=25775, 316nm=16920
Basic: 234nm=16013, 300nm=19700

Surface tension (mN m⁻¹)

72.7

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

500

Very persistent

DT₅₀ (lab at 20 °C)

1000

Very persistent

DT₅₀ (field)

724

Very persistent

DT₉₀ (lab at 20 °C)

1000

Very persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU dossier 2001

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

1.2

Moderately fast

Note

Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7

Value

203

Persistent

Note

Stable pH 5 to pH 9

Water-sediment DT₅₀ (days)

Fast

Water phase only DT₅₀ (days)

1.6

Moderately fast

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

Slightly mobile

K_oc

3983

Notes and range

EU dossier 2014 K_d range 26-120 mL g⁻¹; K_oc range 1200-11000 mL g⁻¹, Soils=6; Other data: K_oc ~ 2500 mL g⁻¹ (DW3)

Freundlich

K_f

35.5

Slightly mobile

K_foc

2091

¹/_n

0.79

Notes and range

EU dossier 2014 K_f range 13-100 mL g⁻¹, K_foc range 580-3921 mL g⁻¹, ¹/_n range 0.72-0.90, Soils =5

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

1.94

Calculated

Transition state

SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate

Value

7.80 X 10^-02

Calculated

Note

Potential for particle bound transport index

High

Calculated

Potential for loss via drain flow

Slightly mobile

Calculated

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

5-hydroxythiabendazole

NOA415696

Animal

benzimidazole-2-carboxamide

Water

benzimidazole-2-carboxylic acid

1,2-dihydro-3-hydroxy-quinoxaline

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

96.5

Low potential

CT₅₀ (days)

Not available

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 5000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

> 10

Rat

High

(ppm diet)

Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)

Rat Reproductive NOAEL

Moderate

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2250

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 5620 mg kg feed⁻¹

Colinus virginianus

Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)

34.9

Colinus virginianus

Moderate

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.55

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.012

Oncorhynchus mykiss

Moderate

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

0.81

Daphnia magna

Moderate

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

0.042

Daphnia magna

Moderate

Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)

0.34

Americamysis bahia

Moderate

Sediment dwelling organisms - Acute 96 hour LC₅₀ (mg l⁻¹)

Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l⁻¹)

2.0

Chironomus riparius

Moderate

Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg⁻¹)

3.0

Chironomus riparius

Moderate

Aquatic plants - Acute 7 day EC₅₀, biomass (mg l⁻¹)

Non-target plants

Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)

9.0

Raphidocelis subcapitata

Moderate

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

3.2

Unknown species

Low

Honeybees (Apis spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

> 34

Moderate

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

> 4.0

Moderate

Unknown mode acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

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 pollinators (1)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Other pollinators (2)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)

> 1000

Eisenia foetida

Low

Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)

4.2

Eisenia foetida

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

1800

>
Typhlodromus pyri

% Effect

0 / 62

Mortality / Fecundity [Dose: 1.8 kg ha⁻¹]
Aphidius rhopalosiphi

Other arthropod (2)

LR₅₀ g ha⁻¹

1800

>
Typhlodromus pyri

% Effect

3 / 5

Mortality / Fecundity [Dose: 1.8 kg ha⁻¹]
Typhlodromus pyri

Soil micro-organisms

Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect

Dose: 9 mg kg⁻¹ soil

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)

> 5000

Rat

Low

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

5000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 0.53

Rat

Other Mammal toxicity endpoints

ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)

0.1

ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)

None allocated

AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)

AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)

0.1

Dermal penetration studies (%)

0.15-1.84%

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

No unacceptable risks to bystanders identified

Occupational

No unacceptable risks to operators or other workers identified

European MRLs

EU MRL pesticide database

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

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

Possible thyroid, liver, spleen and kidney toxicant
USEPA - possible human carcinogen at high doses

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
IMDG Transport Code is usually 9

CLP classification 2013

Environment: H400, H410

EC Risk Classification

N - Dangerous for the environment: R50, R53

EC Safety Classification

S60, S61

WHO Classification

III (Slightly hazardous)

UN Number

Variable with product, usually 3077 or 3082

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

thiabendazole

French

thiabendazole

German

Thiabendazol

Danish

E 233, thiabendazole

Italian

tiabendazolo

Spanish

tiabendazol

Greek

thiabendazol

Polish

tiabendazol

Swedish

tiabendazol

Hungarian

thiabendazole

Dutch

thiabendazool

Record last updated:	26/06/2019
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