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thiophanate-methyl (Ref: NF 44)
** thiophanate ** thiofanate ** banrot ** Translations

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SUMMARY

Thiophanate methyl is an approved EU fungicide used widely to control fungal diseases on crops. It has a low aqueous solubility, low volatility and tends not to be persistent in soil or water systems. It has a low mammalian toxicity, however it is an irritant, a skin sensitiser and may also be mutagen. It is moderately toxic to most aquatic organisms and earthworms but less so to birds and honeybees.

GENERAL INFORMATION Click here for an explantaion of the general chemical status information
for thiophanate-methyl

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; Grapes; Tomatoes; Aubergines

Efficacy & activity: Wheat/Ear blight=Low; Soybean/Leaf blight=Moderate; Soybean/Rust=Moderate; Soybean/White mould=Moderate

Availability status: Current

Introduction & key dates: 1971, first registered Japan

EC Regulation 1107/2009 (repealing 91/414):
Status Approved
Dossier rapporteur/co-rapporteur Sweden/Finland
Date inclusion expires 31/10/2019
EU Candidate for substitution (CfS) No
Listed in EU database Yes

Approved for use () or known to be used () in the following European countries: Click to access a note on the approvals information on this site

AT

BE

BG

CY

CZ

DE

DK

EE

EL

ES

FI

FR

HR

HU

IE

IT

LT

LU

LV

MT

NL

PL

PT

RO

SE

SI

SK

UK

Also used in: Australia, USA

Chemical structure: Click here for further information on the general chemical status information used on this site
Isomerism -
Chemical formula C12H14N4O4S2
Canonical SMILES COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC
Isomeric SMILES No data
International Chemical Identifier key (InChIKey) QGHREAKMXXNCOA-UHFFFAOYSA-N
International Chemical Identifier (InChI) InChI=1S/C12H14N4O4S2/c1-19-11(17)15-9(21)13-7-5-3-4-6-8(7)14-10(22)16-12(18)20-2/h3-6H,1-2H3,(H2,13,15,17,21)(H2,14,16,18,22)
2D structure diagram/image available? Yes

General status: Click here for further information on the general chemical status information used on this site
Pesticide type Fungicide
Substance group Benzimidazole
Minimum active substance purity 950 g/kg
Known relevant impurities EU dossier - DAp, HAp, carbendazim
Substance origin Synthetic
Mode of action Inhibition of mitosis and cell division (Beta-tubulin assembly in mitosis).
CAS RN 23564-05-8
EC number 245-740-7
CIPAC number 262
US EPA chemical code 102001
PubChem CID 3032791
Molecular mass (g mol-1) 342.39
PIN (Preferred Identification Name) dimethyl N,N'-[1,2-phenylenebis(azanediylcarbonothioyl)]dicarbamate
IUPAC name dimethyl 4,4'-(o-phenylene)bis(3-thioallophanate)
CAS name dimethyl (1,2-phenylenebis(iminocarbonothioyl))bis(carbamate)
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) 1
Examples of recorded resistance -
Physical state Colourless to light brown crystalline powder
Related substances & organisms

Formulations:
Property Click here for information on the general product and branding information used on this site 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
  • Senator
  • Frumidor
UK LERAP status None (may vary with mixtures)
Formulation and application details Usually formulated as a suspension concentrate, flowable, ULV or wettable powder.


ENVIRONMENTAL FATE

for thiophanate-methyl

Property Click here for information on the parameters used to describe environmental fate on this site Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with fate data Interpretation Click here for information on the way in which we interpret environmental fate data
Solubility - In water at 20oC (mg l-1) 18.5 A5 Low
Solubility - In organic solvents at 20oC (mg l-1) 8400 A5 - Ethyl acetate -
0.47 A5 - n-Hexane -
7800 A5 - Methanol -
110 A5 - Xylene -
Melting point (oC) Decomposes before melting A5 -
Boiling point (oC) Decomposes before boiling A5 -
Degradation point (oC) 165 A5 -
Flashpoint (oC) Not expected to self ignite; Not highly flammable A5 -
Octanol-water partition coefficient at pH 7, 20oC P 2.51 X 1001 Calculated -
Log P 1.40 A5 - @ 25 DegC Low
Bulk density (g ml-1)/Specific gravity 1.45 A5 -
Dissociation constant (pKa) at 25oC 7.28 A5 -
Note: Weak acid
Vapour pressure at 20oC (mPa) 9.0 X 10-03 A5 Low volatility
Henry's law constant at 25oC (Pa m3 mol-1) 1.67 X 10-04 A5 Non-volatile
GUS leaching potential index Click here for a note on the limitations of the GUS index -0.50 Calculated Low leachability
SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate Click here for a note on the limitations of the SCI-GROW index Value 1.45 X 10-04 Calculated -
Note -
Potential for particle bound transport index Click here for a note on the limitations of the potential for particle bound transport index - Calculated Low
Maximum UV-vis absorption L mol-1 cm-1 268nm = 19046, 305nm = shoulder A3 -
Surface tension (mN m-1) 72.2 A5 -

Degradation:
Property Click here for information on the parameters used to describe substance degradation Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with degradation data Interpretation Click here for information on the way in which we interpret substance degradation data
General biodegradability Not readily biodegradable
Soil degradation (days) (aerobic) DT50 (typical) 0.5 Click here to see a warning relating to modelling and this active substance A5 Non-persistent
DT50 (lab at 20oC) 0.5 A5 Non-persistent
DT50 (field) 2.0 A5 Non-persistent
DT90 (lab at 20oC) 1.66 A5 -
DT90 (field) 13,3 A5 -
DT50 modelling endpoint - - -
Note EU 2016 dossier Lab studies DT50 range 0.29-0.70 days, DT90 range 0.96-2.3 days, Soils=4; Field studies DT50 range 1.0-3.3 days, DT90 range 6.0-17.0, Soils=4
Dissipation rate RL50 on plant matrix Value 29.6 R3 -
Note Undercover ornamentals, leaves, n=1
Dissipation rate RL50 on and in plant matrix Value 4.2 R4 -
Note Published literature RL50 range 1.0-15.4 days, 11 field grown crops, various matrices, n=17
Aqueous photolysis DT50 (days) at pH 7 Value 2.2 A5 Moderately fast
Note Data for natural sunlight at pH 5
Aqueous hydrolysis DT50 (days) at 20oC and pH 7 Value 46.8 A5 Moderately persistent
Note pH sensitive: DT50 Stable - 867 days at pH 5; 1.0 days at pH 9, all at 22 degC
Water-sediment DT50 (days) 2 A5 Fast
Water phase only DT50 (days) 3 A5 Moderately fast

Soil adsorption and mobility:
Property Click here for information on the parameters used to describe substance adsorption and mobility Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with adsorption and mobility data Interpretation Click here for information on the way in which we interpret substance adsorption and mobility
Linear Kd - - -
Koc -
Notes and range -
Freundlich Kf 2.41 A5 Moderately mobile
Kfoc 220
1/n 0.86
Notes and range EU 2016 dossier Kf range 0.27-14.1 mL/g, Kfoc range 54-859 mL/g, 1/n range 0.75-0.99, Soils=10
pH sensitivity Some studies suggest that adsorption is stronger in acid soils

Key metabolites:
Metabolite Formation medium Estimated maximum occurrence fraction 1107/2009 relevancy Click here for further information on 1107/2009 relevancy
carbendazim (Ref: BAS 346F) This metabolite may cause environmental pollution, click here for further information Soil   0.758   Major fraction, Relevant
methyl 4-(2-(methoxycarbonylamino)benzothiazoyl)allophanate (Ref: CM-0237) Soil   0.098   Minor fraction, Relevant

Other known metabolites:
Metabolite name and reference Aliases Formation medium / Rate Estimated maximum occurrence fraction Metabolising enzymes
dimethyl 4,4-(4-hydroxy-ortho-phenylene)bis(3-thioallophanate) 4-OH-thiophanate-methyl Animal - -
methyl 4-(2-(3-methoxycarbonyl-2-thioureido)phenyl)allophanate DX-105 Water (photoylsis), Rat, Plant - -
dimethyl 4,4-(ortho-phyenylene)bis(allophanate)) FH-432; Allophanate Water, Animal, Plant - -
dimethyl 4,4-)4-hydroxy-ortho-phenylene)bis(allophanate) 4-OH-FH-432 Rat - -
dimethyl 4,4-)4-hydroxy-ortho-phenylene)bis(allophanate) sulphate 4-OH-FH-432-S Rat - -
[2-N-methoxy carbonyl thioureido) phenylene] thiourea AV-1951 Water - -
methyl-N-(2-aminophenylaminocarbonothioyl)carbamate FH-73 - - -
methyl (4-hydroxy-1H-benzimidazol-2-yl)carbamate 4-OH-MBC Animal - -
methyl (4-hydroxy-1H-benzimidazol-2-yl)carbamate sulphate 4-OH-MBC-S Rodent - -
methyl (5-hydroxy-1H-benzoimidazol-2-yl)carbamate 5-OH-MBC Animal - -
methyl (5-hydroxy-1H-benzoimidazol-2-yl)carbamate sulphate 5-OH-MBC-s Animal - -
2-amino-1H-benzimidazole 2-AB Water-sediment systems, Soil, Animal, Plant - -
2-amino(-4-hydroxy)benzimidazole 4-OH-2-AB - - -
2-amino-1H-benzimidazol-5-ol 5-OH-2-AB Hen - -
dimethyl 4,4-(4-hydroxy-ortho-phenylene)bis(3-thioallophanate) sulphate 5-OH-thiophanate-menthyl sulfate Rodent - -
dimethyl 4,4-(3-hydroxy-ortho-phenylene)bis(3-thioallophanate) 3-OH-thiophanate-methyl Animal - -


ECOTOXICOLOGY

for thiophanate-methyl

Property Click here for information on the parameters used to describe substance ecotoxicology Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with ecotoxicology data Interpretation Click here for information on the way in which we interpret substance ecotoxicology
Bio-concentration factor BCF (l kg-1) 75 Q2 Estimated Low potential
CT50 (days) Not available -
Mammals - Acute oral LD50 (mg kg-1) > 5000 A5 Rat Low
Mammals - Short term dietary NOEL (mg kg-1) - L3 Rat -
(ppm diet) > 2.5 -
Birds - Acute LD50 (mg kg-1) > 4640 A5 Anas platyrhynchos Low
Birds - Short term dietary (LC50/LD50) > 10000 mg kg feed-1 A4 Unknown species -
Fish - Acute 96 hour LC50 (mg l-1) 11.0 A5 Oncorhynchus mykiss Moderate
Fish - Chronic 21 day NOEC (mg l-1) 0.32 A5 Salmo gairdneri Moderate
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) 5.4 A5 Daphnia magna Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) 0.18 A5 Daphnia magna Moderate
Aquatic crustaceans - Acute 96 hour LC50 (mg l-1) 1.0 F3 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) 0.5 A5 Chironomus riparius, emergence Moderate
Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg-1) - - -
Aquatic plants - Acute 7 day EC50, biomass (mg l-1) 4.7 F3 Lemna gibba Moderate
Non-target plants > 1570 A5 Cabbage, Corn, Cucumber, Lettuce, Oats, Onions, Ryegrass, Tomatoes
Vegetative vigour, ER50
as g/ha
-
> 1680 A5 Cabbage, Corn, Cucumber, Lettuce, Oats, Onions, Ryegrass, Tomatoes
Seedling emergence, ER50
as g/ha
-
Algae - Acute 72 hour EC50, growth (mg l-1) > 25.4 A5 Pseudokirchneriella subcapitata Low
Algae - Chronic 96 hour NOEC, growth (mg l-1) - - -
Honeybees Contact acute 48 hour LD50 (μg bee-1) > 100 A5 Low
Oral acute 48 hour LD50 (μg bee-1) > 100 A5 Low
Unknown mode acute 48 hour LD50 (μg bee-1) - - -
Earthworms - Acute 14 day LC50 (mg kg-1) > 13.2 A5 Eisenia foetida Moderate
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) 0.85 A5 Eisenia foetida Moderate
Other soil macro-organisms - e.g. Collembola LR50 / EC50 / NOEC / % Effect - - -
Other arthropod (1) LR50 g ha-1 Harmless Dose: 400 g ha-1
AA3 Aphidius rhopalosiphi
-
% Effect 74 Parasitastion
Dose: 1.58 kg ha-1
A5 Aphidius rhopalosiphi
-
Other arthropod (2) LR50 g ha-1 1575 >
A5 Typhlodromus pyri
-
% Effect 4 Mortality
Dose: 0.07 kg ha-1
A5 Typhlodromus pyri
-
Soil micro-organisms Nitrogen mineralisation: No adverse effect
Carbon mineralisation: No adverse effect
A5
Dose: 5 kg ha-1
-
Mesocosm study data NOEAEC mg l-1 - - -
NOEAEC mg l-1 - - -


HUMAN HEALTH AND PROTECTION

for thiophanate-methyl

General:
Property Click here for information on the parameters used to describe human health and protection issues Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with human health and protection data Interpretation Click here for information on the way in which we interpret human health and protection data
Threshold of Toxicological Concern (Cramer Class) Click here for a note on the limitations of the Cramer class High (class III) - -
Mammals - Acute oral LD50 (mg kg-1) > 5000 A5 Rat Low
Mammals - Dermal LD50 (mg kg-1 body weight) > 2000 A5 Rat -
Mammals - Inhalation LC50 (mg l-1) 1.7 A5 Rat, 4 hr (whole body) -
Other Mammal toxicity endpoints - -
ADI - Acceptable Daily Intake (mg kg-1bw day-1) 0.08 A5 Dog, SF=100, under review -
ARfD - Acute Reference Dose (mg kg-1bw day-1) 0.2 A5 Rabbit, SF=100, under review -
AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) Not established A1 -
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) 0.08 A5 Dog, SF=100, under review -
Dermal penetration studies (%) 10 A5 -
Dangerous Substances Directive 76/464 - - -
Exposure Limits - - -
Exposure Routes Public Low risk for bystanders and residents
Occupational Use of PPE/PPC recommended to reduce exposure risks
European MRLs Click here for the EU MRL pesticide database
Drinking Water Standards - - -
Drinking Water MAC (μg l-1) - 10A5 -

Health issues:
Carcinogen Mutagen Endocrine disrupter Reproduction / development effects Cholinesterase inhibitor Neurotoxicant

-

Respiratory tract irritant Skin irritant Skin sensitiser Eye irritant Phototoxicant

General human health issues Mutagenic potential
USEPA - possible human carcinogen
Possible liver, kidney & thyroid toxicant

: Yes, known to cause a problem
: No, known not to cause a problem
: Possibly, status not identified
- : No data found

Handling issues:
Property Click here for information on the parameters used to describe substance handling issues Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with data on handling issues Interpretation Click here for information on the way in which we interpret data on handling issues
General Click here for a description of the International Maritime Dangerous Goods (IMDG) codes Prevent generation of dust
Some explosive potential but generally considered not to have explosive or oxidising properties
IMDG Transport Code is usually 9
CLP classification 2013 Health: H317, H332, H340, H351, H373
Environment: H400, H410
EC Risk Classification Click here to view information omn the EU risk phrases Mutagenic category 3: R68
Xn - Harmful: R20, R43
N - Dangerous for the environment: R50, R53
EC Safety Classification Click here to view information omn the EU safety phrases S2, S36/37, S46, S60, S61
WHO Classification U - Unlikely to present an acute hazard
US EPA Classification (formulation) IV - Caution - Not acutely toxic
UN Number Usually 3077
Waste disposal & packaging Click here for a description of UN packaging marks Packaging Group III (minor danger)


TRANSLATIONS

for thiophanate-methyl

Language Name
English thiophanate-methyl
French thiophanate-methyle
German Thiophanat-methyl
Danish thiophanate-methyl
Italian tiofanato-metile
Spanish tiofanato de metilo
Greek -
Slovenian tiofanat-metil
Polish tiofanat metylowy
Swedish tiofanatmetyl
Hungarian tiophanate-methyl
Dutch thiofanaat-methyl

Record last updated: Monday 05 November 2018
Contact: aeru@herts.ac.uk
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