| thiophanate |
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GENERAL INFORMATION 
for thiophanate
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
EC Regulation 1107/2009 (repealing 91/414):
| Status | Approved only as the methyl variant |
| Dossier rapporteur/co-rapporteur | Germany |
| 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 | C14H18N4O4S2 |
| Canonical SMILES | CCOC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OCC |
| Isomeric SMILES | No data |
| 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 |
General status:
| Pesticide type | Fungicide | |
| Substance group | Benzimidazole | |
| 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 | |
| Molecular mass (g mol-1) | 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 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 crystals | |
| 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 wettable powder. | |||
ENVIRONMENTAL FATE
for thiophanate
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Solubility - In water at 20oC (mg l-1) | - | - | - | |
| Solubility - In organic solvents at 20oC (mg l-1) | - | - | - | |
| Melting point (oC) | - | - | - | |
| Boiling point (oC) | - | - | - | |
| Degradation point (oC) | - | - | - | |
| Flashpoint (oC) | - | - | - | |
| Octanol-water partition coefficient at pH 7, 20oC | P | - | - | - |
| Log P | - | - | - | |
| Bulk density (g ml-1)/Specific gravity | - | - | - | |
| Dissociation constant (pKa) at 25oC | - | - | - | |
| Note: | ||||
| Vapour pressure at 20oC (mPa) | - | - | - | |
| Henry's law constant at 25oC (Pa m3 mol-1) | - | - | - | |
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 | - | - | - |
| Note | - | |||
| Potential for particle bound transport index |
- | - | - | |
| Maximum UV-vis absorption L mol-1 cm-1 | - | - | - | |
| Surface tension (mN m-1) | - | - | - | |
Degradation:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
General biodegradability | - |
| Soil degradation (days) (aerobic) | DT50 (typical) | - | - | - |
| DT50 (lab at 20oC) | - | - | - | |
| DT50 (field) | - | - | - | |
| DT90 (lab at 20oC) | - | - | - | |
| 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 20oC and pH 7 | Value | - | - | - |
| Note | - | |||
| Water-sediment DT50 (days) | - | - | - | |
| Water phase only DT50 (days) | - | - | - | |
Soil adsorption and mobility:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Linear | Kd | - | - | - |
| Koc | - | |||
| Notes and range | - | |||
| Freundlich | Kf | - | - | - |
| Kfoc | - | |||
| 1/n | - | |||
| Notes and range | - | |||
| pH sensitivity | - | |||
Key metabolites:
| Metabolite | Formation medium | Estimated maximum occurrence fraction | 1107/2009 relevancy |
|
| carbendazim (Ref: BAS 346F) | Soil | - | Major fraction, Relevant | |
| allophanate | Soil | - | - | |
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 | - | - |
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Bio-concentration factor | BCF (l kg-1) | - | - | - |
| CT50 (days) | - | - | ||
| Mammals - Acute oral LD50 (mg kg-1) | > 5000 | A5 Rat, as methyl variant | Low | |
| Mammals - Short term dietary NOEL | (mg kg-1) | - | L3 Rat, as methyl variant | - |
| (ppm diet) | > 2.5 | - | ||
| Birds - Acute LD50 (mg kg-1) | > 4640 | A5 Anas platyrhynchos, as methyl variant | Low | |
| Birds - Short term dietary (LC50/LD50) | > 10000 mg kg feed-1 | A4 Unknown species, as methyl variant | - | |
| Fish - Acute 96 hour LC50 (mg l-1) | 11.0 | A5 Oncorhynchus mykiss, as methyl variant | Moderate | |
| Fish - Chronic 21 day NOEC (mg l-1) | 0.32 | A5 Salmo gairdneri, as methyl variant | Moderate | |
| Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) | 5.4 | A5 Daphnia magna, as methyl variant | Moderate | |
| Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) | 0.18 | A5 Daphnia magna, as methyl variant | Moderate | |
| Aquatic crustaceans - Acute 96 hour LC50 (mg l-1) | 1.0 | F3 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 | A5 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 | F3 Lemna gibba, as methyl variant | Moderate | |
| Non-target plants | - | - | - | |
| - | - | - | ||
| Algae - Acute 72 hour EC50, growth (mg l-1) | > 25.4 | A5 Pseudokirchneriella subcapitata, as methyl variant | Low | |
| Algae - Chronic 96 hour NOEC, growth (mg l-1) | - | - | - | |
| Honeybees | Contact acute 48 hour LD50 (μg bee-1) | > 100 | A5, as methyl variant | Low |
| Oral acute 48 hour LD50 (μg bee-1) | > 100 | A5, as methyl variant | Low | |
| Unknown mode acute 48 hour LD50 (μg bee-1) | - | - | - | |
| Earthworms - Acute 14 day LC50 (mg kg-1) | > 13.2 | A5 Eisenia foetida, as methyl variant | Moderate | |
| Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) | 0.85 | A5 Eisenia foetida, as methyl variant | Moderate | |
| Other soil macro-organisms - e.g. Collembola | LR50 / EC50 / NOEC / % Effect | - | - | - |
| Other arthropod (1) | LR50 g ha-1 | - | - | - |
| % Effect | - | - | - | |
| Other arthropod (2) | LR50 g ha-1 | - | - | - |
| % Effect | - | - | - | |
| Soil micro-organisms | - | - | - | |
| Mesocosm study data | NOEAEC mg l-1 | - | - | - |
| NOEAEC mg l-1 | - | - | - | |
HUMAN HEALTH AND PROTECTION
for thiophanate
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, as methyl variant | Low | |
| Mammals - Dermal LD50 (mg kg-1 body weight) | > 2000 | A5 Rat, as methyl variant | - | |
| Mammals - Inhalation LC50 (mg l-1) | 1.7 | A5 Rat, as methyl variant | - | |
| Other Mammal toxicity endpoints | - | - | ||
| ADI - Acceptable Daily Intake (mg kg-1bw day-1) | 0.08 | A5 Dog, SF=100, as methyl variant | - | |
| ARfD - Acute Reference Dose (mg kg-1bw day-1) | 0.2 | A5 Rabbit, SF=100, as methyl variant | - | |
| AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) | - | - | - | |
| AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) | 0.08 | A5 Dog, SF=100, as methyl variant | - | |
| Dermal penetration studies (%) | 10 | A5 | - | |
| Dangerous Substances Directive 76/464 | - | - | - | |
| Exposure Limits | - | - | - | |
| Exposure Routes | Public | - | ||
| Occupational | - | |||
| European MRLs | Click here for the EU MRL pesticide database | |||
| Drinking Water Standards | - | - | - | |
| Drinking Water MAC (μg l-1) | - | - | - | |
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 | |||||||
: 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 IMDG Transport Code is usually 9 |
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| CLP classification 2013 | Health: H317, H332, H341 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) | |||
| Language | Name |
| English | thiophanate |
| French | thiophanate |
| 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