| captafol (Ref: Ortho-5865) |
 |
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SUMMARY
Captafol is a broad spectrum fungicide that is not approved for use in the EU. It has a low aqueous solubility, is non-volatile and, based on its chemical properties, would not normally be expected to leach to groundwater. It is not persistent in soil or water systems. Captafol has a low mammalian toxicity and is not expected to bioaccumulate. It is reported as a carcinogen and irritant. It is moderately toxic to birds, honeybees, earthworms and most aquatic organisms. GENERAL INFORMATION 
for captafol
Description: A broad-spectrum phthalimide, contact fungicide often used to control diseases of fruit and other crops
Example pests controlled: Foliage and fruit fungal diseases
Example applications: Fruit including apples, citrus, cranberry, blueberry, prunes, stone fruit; Potatoes; Tomatoes; Coffee; Peanuts; Onions;
Efficacy & activity: -
Availability status: Unknown
Introduction & key dates: circa 1962
EC Regulation 1107/2009 (repealing 91/414):
| Status | Not approved |
| Dossier rapporteur/co-rapporteur | - |
| Date inclusion expires | Expired/Banned |
| EU Candidate for substitution (CfS) | - |
| 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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Chemical structure:
| Isomerism | A chiral molecule, an isomeric mixture |
| Chemical formula | C10H9Cl4NO2S |
| Canonical SMILES | C1C=CCC2C1C(=O)N(C2=O)SC(C(Cl)Cl)(Cl)Cl |
| Isomeric SMILES | No data |
| International Chemical Identifier key (InChIKey) | JHRWWRDRBPCWTF-UHFFFAOYSA-N |
| International Chemical Identifier (InChI) | InChI=1S/C10H9Cl4NO2S/c11-9(12)10(13,14)18-15-7(16)5-3-1-2-4-6(5)8(15)17/h1-2,5-6,9H,3-4H2 |
| 2D structure diagram/image available? | Yes |
Cambridge Crystallographic Data Centre diagrams:
| Common Name | Relationship | Link |
| Captafol | Unstated isomer |  |
General status:
| Pesticide type | Fungicide | |||
| Substance group | Phthalimide | |||
| Minimum active substance purity | - | |||
| Known relevant impurities | - | |||
| Substance origin | Synthetic | |||
| Mode of action | Acts by inhibiting the germination of spores. Multi-site activity. | |||
| CAS RN | 2425-06-1 | |||
| EC number | 219-363-3 | |||
| CIPAC number | 185 | |||
| US EPA chemical code | 081701 | |||
| PubChem CID | 17038 | |||
| CLP index number | 613-046-00-7 | |||
| Molecular mass (g mol-1) | 349.06 | |||
| PIN (Preferred Identification Name) | 2-[(1,1,2,2-tetrachloroethyl)sulfanyl]-3a,4,7,7a-tetrahydro-1H-isoindole-1,3(2H)-dione | |||
| IUPAC name | N-(1,1,2,2-tetrachloroethylthio)cyclohex-4-ene-1,2-dicarboximide | |||
| CAS name | 3a,4,7,7a-tetrahydro-2-[(1,1,2,2-tetrachloroethyl)thio]-1H-isoindole-1,3(2H)-dione | |||
| Other status information | Chemical subject to PIC regulations; Rotterdam Convention (Class Ia) | |||
| 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) | M4 | |||
| Examples of recorded resistance | - | |||
| Physical state | Colourless/yellow 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 | No UK approval for use as a pesticide under EC Regulation 1107/2009 | |||
| Formulation and application details | Available in a variety of formulations including dusts, wettable powders, aqueous suspensions and suspension concentrates. | |||
ENVIRONMENTAL FATE
for captafol
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Solubility - In water at 20oC (mg l-1) | 1.4 | G4 | Low | |
| Solubility - In organic solvents at 20oC (mg l-1) | 25000 | L3 - Benzene | - | |
| 17000 | L3 - Toluene | - | ||
| 100000 | L3 - Xylene | - | ||
| 43000 | L3 - Acetone | - | ||
| Melting point (oC) | 161 | A4 | - | |
| Boiling point (oC) | Decomposes before boiling | L3 | - | |
| Degradation point (oC) | 161 | L3 | - | |
| Flashpoint (oC) | - | - | - | |
| Octanol-water partition coefficient at pH 7, 20oC | P | 6.76 X 1003 | Calculated | - |
| Log P | 3.83 | G4 | High | |
| Bulk density (g ml-1)/Specific gravity | - | - | - | |
| Dissociation constant (pKa) at 25oC | - | - | - | |
| Note: | ||||
| Vapour pressure at 20oC (mPa) | 1.30 X 10-09 | G4 | Low volatility | |
| Henry's law constant at 25oC (Pa m3 mol-1) | 3.30 X 10-01 | H3 | Moderately volatile | |
GUS leaching potential index  |
1.11 | Calculated | Low leachability | |
| SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate |
Value | 2.30 X 10-02 | Calculated | - |
| Note | - | |||
| Potential for particle bound transport index |
- | Calculated | Medium | |
| 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) | 39 | F4 | Moderately persistent |
| DT50 (lab at 20oC) | - | - | - | |
| DT50 (field) | 7.0 | DW4 | Non-persistent | |
| DT90 (lab at 20oC) | - | - | - | |
| DT90 (field) | - | - | - | |
| DT50 modelling endpoint | - | - | - | |
| Note | FAO state DT50 23-55 days; Other literature values DT50 range from 2-11 days | |||
| 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 | - | L3 | - |
| Note | Rapidly hydrolysed in acidic and alkaline conditions | |||
| Water-sediment DT50 (days) | - | - | - | |
| Water phase only DT50 (days) | - | - | - | |
Soil adsorption and mobility:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Linear | Kd | - | H3 | Slightly mobile |
| Koc | 2000 | |||
| Notes and range | Best available data | |||
| Freundlich | Kf | - | - | - |
| Kfoc | - | |||
| 1/n | - | |||
| Notes and range | - | |||
| pH sensitivity | - | |||
Other known metabolites:
| Metabolite name and reference | Aliases | Formation medium / Rate | Estimated maximum occurrence fraction | Metabolising enzymes |
| tetrahydrophthalimidic acid | - | Animals | - | - |
| dichloroactetic acid | - | Animals | - | - |
| phthalic acid | - | Animals | - | - |
| ammonia | - | Animals | - | - |
| tetrahydrophthalimide | THPI | Animals | - | - |
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Bio-concentration factor | BCF (l kg-1) | 27 | Q2 Estimated | Low potential |
| CT50 (days) | Not available | - | ||
| Mammals - Acute oral LD50 (mg kg-1) | > 5500 | L3 Rat | Low | |
| Mammals - Short term dietary NOEL | (mg kg-1) | - | L2 Rat, 2 year | - |
| (ppm diet) | 500 | - | ||
| Birds - Acute LD50 (mg kg-1) | 101700 | F3 Anas platyrhynchos | Low | |
| Birds - Short term dietary (LC50/LD50) | - | - | - | |
| Fish - Acute 96 hour LC50 (mg l-1) | 0.5 | L3 Oncorhynchus mykiss | Moderate | |
| Fish - Chronic 21 day NOEC (mg l-1) | > 0.25 | J3 Cyprinidae, 13 day | Moderate | |
| Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) | > 3.34 | L3 Daphnia magna | Moderate | |
| Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) | - | - | - | |
| Aquatic crustaceans - Acute 96 hour LC50 (mg l-1) | - | - | - | |
| Sediment dwelling organisms - Acute 96 hour LC50 (mg l-1) | - | - | - | |
| Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l-1) | - | - | - | |
| Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg-1) | - | - | - | |
| Aquatic plants - Acute 7 day EC50, biomass (mg l-1) | - | - | - | |
| Non-target plants | - | - | - | |
| - | - | - | ||
| Algae - Acute 72 hour EC50, growth (mg l-1) | - | - | - | |
| Algae - Chronic 96 hour NOEC, growth (mg l-1) | - | - | - | |
| Honeybees | Contact acute 48 hour LD50 (μg bee-1) | - | - | - |
| Oral acute 48 hour LD50 (μg bee-1) | - | - | - | |
| Unknown mode acute 48 hour LD50 (μg bee-1) | > 96.7 | F3 72 Hr | Moderate | |
| Earthworms - Acute 14 day LC50 (mg kg-1) | > 351 | F4 Eisenia foetida | Moderate | |
| Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) | - | - | - | |
| 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 captafol
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) | > 5500 | L3 Rat | Low | |
| Mammals - Dermal LD50 (mg kg-1 body weight) | > 5000 | F4 Rat | - | |
| Mammals - Inhalation LC50 (mg l-1) | 0.72 | L3 Rat | - | |
| Other Mammal toxicity endpoints | - | - | ||
| ADI - Acceptable Daily Intake (mg kg-1bw day-1) | - | - | - | |
| ARfD - Acute Reference Dose (mg kg-1bw day-1) | - | - | - | |
| AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) | - | - | - | |
| AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) | - | - | - | |
| Dermal penetration studies (%) | - | - | - | |
| Dangerous Substances Directive 76/464 | - | - | - | |
| Exposure Limits | [UK LT TWA 8hr: 0.1 mg/m3] | Occupation Exposure | - | |
| Exposure Routes | Public | - | ||
| Occupational | Contact dermatitis, severe irritation of the respiratory tract, eye damage and other systemic effects are reported | |||
| 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 | IARC group 2A carcinogen; USEPA - probable human carcinogen May cause dermatitis May cause conjunctivitis and periorbital edema |
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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 |
Corrosive to metals Avoid generation of dust |
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| CLP classification 2013 | Health: H317, H350 Environment: H400, H410 |
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| EC Risk Classification |
Carcinogen category 2: R45 Xn - Harmful: R43 N - Dangerous for the environment: R50, R53 |
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| EC Safety Classification |
S45, S53, S61, S60 | |||
| WHO Classification | Ia | - | Extremely hazardous | |
| US EPA Classification (formulation) | IV | - | Caution - Not acutely toxic | |
| UN Number | - | |||
| Waste disposal & packaging |
- | |||
| Language | Name |
| English | captafol |
| French | captafole |
| German | Captafol |
| Danish | captafol |
| Italian | captafol |
| Spanish | captafol |
| Greek | - |
| Slovenian | kaptafol |
| Polish | kaptafol |
| Swedish | - |
| Hungarian | - |
| Dutch | captafol |
Record last updated: Tuesday 30 October 2018
Contact: aeru@herts.ac.uk