| thiophanate-methyl (Ref: NF 44) |
 |
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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 
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: 
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 |
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Also used in: Australia, USA
Chemical structure:
| 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:
| 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 |
Value | |||
| Example manufacturers & suppliers of products using this active now or historically |
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| Example products using this active |
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| 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 |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| 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  |
-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 |
Value | 1.45 X 10-04 | Calculated | - |
| Note | - | |||
| 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 |
Value | Source/Quality Score/Other Information |
Interpretation |
General biodegradability | Not readily biodegradable |
| Soil degradation (days) (aerobic) | DT50 (typical) | 0.5 |
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 |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| 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 |
|
| carbendazim (Ref: BAS 346F) |
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 |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| 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 |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Threshold of Toxicological Concern (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 | |||
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| Respiratory tract irritant | Skin irritant | Skin sensitiser | Eye irritant | Phototoxicant | ||||
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| General human health issues | Mutagenic potential USEPA - possible human carcinogen Possible liver, kidney & thyroid toxicant |
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: Yes, known to cause a problem
: No, known not to cause a problem
: Possibly, status not identified
- : No data found
Handling issues:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| General |
Prevent generation of dust Some explosive potential but generally considered not to have explosive or oxidising properties IMDG Transport Code is usually 9 |
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| CLP classification 2013 | Health: H317, H332, H340, H351, H373 Environment: H400, H410 |
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| EC Risk Classification |
Mutagenic category 3: R68 Xn - Harmful: R20, R43 N - Dangerous for the environment: R50, R53 |
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| EC Safety Classification |
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 |
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