Thiophanate

Thiophanate	Last updated: 10/09/2023
(Also known as: thiophanate; thiofanate; banrot; thiophanate ethyl)

SUMMARY

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
	Ecotoxicity Moderate alert: Fish acute ecotoxicity: Moderate; Fish chronic ecotoxicity: Moderate; Daphnia acute ecotoxicity: Moderate; Daphnia chronic ecotoxicity: Moderate; Earthworms acute ecotoxicity: Moderate; Earthworms chronic ecotoxicity: Moderate	Human health High alert: Genotoxic; Reproduction/development effects

GENERAL INFORMATION

Description

A systemic fungicide effective with protective and curative activity against a broad spectrum of diseases in fruit, vegetables and other crops

Example pests controlled

Eyespot; Scab; Powdery mildew; Grey mould; Leaf spot; Rusts; brown spot; Brown Rot; Root rots

Example applications

Apples & pears; Small grains; Curcubits; Soybeans; Peanuts, Pecans; Garlic & onions; Almonds; Strawberries

Efficacy & activity

Wheat/Ear blight=Low

Availability status

Current

Introduction & key dates

1971, first registered Japan

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

Germany

Date EC 1107/2009 inclusion expires

Expired

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

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

Chemical structure

Isomerism

None

Chemical formula

C₁₄H₁₈N₄O₄S₂

Canonical SMILES

CCOC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OCC

Isomeric SMILES

International Chemical Identifier key (InChIKey)

YFNCATAIYKQPOO-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C14H18N4O4S2/c1-3-21-13(19)17-11(23)15-9-7-5-6-8-10(9)16-12(24)18-14(20)22-4-2/h5-8H,3-4H2,1-2H3,(H2,15,17,19,23)(H2,16,18,20,24)

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
thiophanate	-

General status

Pesticide type

Fungicide

Substance groups

Carbamate fungicide

Minimum active substance purity

Known relevant impurities

Substance origin

Synthetic

Mode of action

Inhibition of mitosis and cell division (Beta-tubulin assembly in mitosis).

CAS RN

23564-06-9

EC number

245-741-2

CIPAC number

262

US EPA chemical code

103401

PubChem CID

3032792

CLP index number

No data found

Molecular mass

370.45

PIN (Preferred Identification Name)

diethyl N,N'-(1,2-phenylenebis(azanediylcarbonothioyl))dicarbamate

IUPAC name

diethyl 4,4'-(o-phenylene)bis(3-thioallophanate)

CAS name

diethyl N,N'-(1,2-phenylenebis(iminocarbonothioyl))bis(carbamate)

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)

Examples of recorded resistance

Physical state

Colourless crystals

Related substances & organisms

thiophanate-methyl

Formulations

Property

Value

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

Bayer Environ
Headland
Makhteshim-Agan
Scotts
Nufarm

Example products using this active

Snare
Mildothane Turf Liquid
3336Plus
Topsin M

Formulation and application details

Usually formulated as a wettable powder

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

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

Melting point (°C)

Boiling point (°C)

Degradation point (°C)

Flashpoint (°C)

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

Log P

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

Dissociation constant pKa) at 25 °C

Vapour pressure at 20 °C (mPa)

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

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)

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

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

K_oc

Notes and range

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

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

Value

Cannot be calculated

Note

Potential for particle bound transport index

Potential for loss via drain flow

Bio-concentration factor

BCF (l kg⁻¹)

CT₅₀ (days)

Known soil metabolites

Metabolite

Major/Minor fraction

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

Estimated maximum occurrence fraction

Notes

carbendazim (Ref: BAS 346F)

Major fraction

allophanate

Known groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

5-OH-MBC-sulfate

Animal

5-OH-MBC

Animal

4-OH-thiophanate-methyl, MBC

Animal

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 5000

Rat as methyl variant

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat as methyl variant

(ppm diet)

> 2.5

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

Birds - Acute LD₅₀ (mg kg⁻¹)

> 4640

Anas platyrhynchos as methyl variant

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 10000 mg kg feed⁻¹

Unknown species as methyl variant

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

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

> 13.2

Eisenia foetida as methyl variant

Moderate

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

0.85

Eisenia foetida as methyl variant

Moderate

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)

> 100

as methyl variant

Low

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

> 100

as methyl variant

Low

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)

11.0

Oncorhynchus mykiss as methyl variant

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.32

Salmo gairdneri as methyl variant

Moderate

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

5.4

Daphnia magna as methyl variant

Moderate

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

0.18

Daphnia magna as methyl variant

Moderate

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

1.0

Americamysis bahia as methyl variant

Moderate

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

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

0.5

Chironomus riparius as methyl variant

Moderate

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

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

4.7

Lemna gibba as methyl variant

Moderate

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

> 25.4

Pseudokirchneriella subcapitata as methyl variant

Low

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)

> 5000

Rat as methyl variant

Low

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

2000

Rat as methyl variant

Mammals - Inhalation LC₅₀ (mg l⁻¹)

1.7

Rat as methyl variant

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

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

Eye irritant

Phototoxicant

No data found

General human health issues

Mutagenic potential; Suspected of causing genetic defects
CLP data - suspected carcinogen

Handling issues

Property

Value and interpretation

General

Prevent generation of dust
Some explosive potential
IMDG Transport Hazard Class 6.1

CLP classification 2013

Health: H317, H332, H341, H351
Environment: H400, H410

WHO Classification

U (Unlikely to present an acute hazard)

UN Number

UN2757

Waste disposal & packaging

Packaging Group III (minor danger)

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

thiophanate

French

thiophanate

German

Thiophanat-methyl

Danish

thiophanate-methyl

Italian

tiofanato-metile

Spanish

tiofanato de metilo

Greek

Polish

tiofanat metylowy

Swedish

tiofanatmetyl

Hungarian

tiophanate-methyl

Dutch

thiofanaat-methyl

Norwegian

Record last updated:	10/09/2023
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