| dithianon (Ref: BAS 216F) |
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Environmental Fate - Ecotoxicology - Human Health - A to Z Index - Home
GENERAL INFORMATION 
for dithianon
Description: A dicarbonitrile fungicide for control of scab and other foliar diseases excluding powdery mildew
Example pests controlled: Scab (reduction); Downy mildew
Example applications: Apples; Pears; Grapes (table & wine); Blackcurrants
Efficacy & activity: -
Availability status: Current
Introduction & key dates: circa 1965
EC Regulation 1107/2009 (repealing 91/414):
| Status | Approved |
| Dossier rapporteur/co-rapporteur | Austria/Spain |
| Date inclusion expires | 31/05/2021 |
| 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
Chemical structure:
| Isomerism | - |
| Chemical formula | C14H4N2O2S2 |
| Canonical SMILES | C1=CC=C2C(=C1)C(=O)C3=C(C2=O)SC(=C(S3)C#N)C#N |
| Isomeric SMILES | No data |
| International Chemical Identifier key (InChIKey) | PYZSVQVRHDXQSL-UHFFFAOYSA-N |
| International Chemical Identifier (InChI) | InChI=1S/C14H4N2O2S2/c15-5-9-10(6-16)20-14-12(18)8-4-2-1-3-7(8)11(17)13(14)19-9/h1-4H |
| 2D structure diagram/image available? | Yes |
General status:
| Pesticide type | Fungicide | |
| Substance group | Quinone | |
| Minimum active substance purity | 930 g/kg | |
| Known relevant impurities | EU dossier - None declared | |
| Substance origin | Synthetic | |
| Mode of action | Protectant with some curative activity. Multi-site activity. | |
| CAS RN | 3347-22-6 | |
| EC number | 222-098-6 | |
| CIPAC number | 153 | |
| US EPA chemical code | 099201 | |
| PubChem CID | 18771 | |
| Molecular mass (g mol-1) | 296.32 | |
| PIN (Preferred Identification Name) | 5,10-dioxo-5,10-dihydronaphtho[2,3-b][1,4]dithiine-2,3-dicarbonitrile | |
| IUPAC name | 5,10-dihydro-5,10-dioxonaphtho[2,3-b]-1,4-dithiine-2,3-dicarbonitrile | |
| CAS name | 5,10-dihydro-5,10-dioxonaphtho(2,3-b)-1,4-dithiin-2,3-dicarbonitrile | |
| Other status information | Marine pollutant; PAN listed Highly Hazardous Chemical | |
| 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) | M9 | |
| Examples of recorded resistance | - | |
| Physical state | Dark brown fibrous 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 | |||
| Formulation and application details | Often supplied as a soluble concentrate or wettable granules that are mixed with water and applied as a spray. | |||
ENVIRONMENTAL FATE
for dithianon
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Solubility - In water at 20oC (mg l-1) | 0.22 | A5 | Low | |
| Solubility - In organic solvents at 20oC (mg l-1) | 14700 | A5 - Toluene | - | |
| 22200 | A5 - Acetone | - | ||
| 10600 | A5 - Ethyl acetate | - | ||
| 8.77 | A5 - Hexane | - | ||
| Melting point (oC) | 215 | A5 | - | |
| Boiling point (oC) | - | - | - | |
| Degradation point (oC) | 222 | A5 | - | |
| Flashpoint (oC) | Not expected to self ignite; Not highly flammable | A5 | - | |
| Octanol-water partition coefficient at pH 7, 20oC | P | 1.58 X 1003 | Calculated | - |
| Log P | 3.2 | A4 - @ pH 2.0 | High | |
| Bulk density (g ml-1)/Specific gravity | 1.58 | L3 | - | |
| Dissociation constant (pKa) at 25oC | Not applicable | A5 | - | |
| Note: No dissociation | ||||
| Vapour pressure at 20oC (mPa) | 1.0 X 10-07 | A3 | Low volatility | |
| Henry's law constant at 25oC (Pa m3 mol-1) | 1.347 X 10-07 | A4 | Non-volatile | |
GUS leaching potential index  |
0.45 | Calculated | Low leachability | |
| SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate |
Value | 8.09 X 10-03 | Calculated | - |
| Note | - | |||
| Potential for particle bound transport index |
- | Calculated | Medium | |
| Maximum UV-vis absorption L mol-1 cm-1 | In CH3CN: 199nm = 35932, 233nm = 20542, 330nm = 5083, 290.5nm = 6535; [pH 1.3: 199nm = 18102, 237nm = 15110, 342nm = 4489, 290.5nm = 5100; [pH 6.9: 199nm = 22380, 250nm = 15110, 350nm = 7204, 290.5nm = 8724 | A5 | - | |
| Surface tension (mN m-1) | 72.7 | A5 at 20oC | - | |
Degradation:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
General biodegradability | - |
| Soil degradation (days) (aerobic) | DT50 (typical) | 10.5 | A5 | Non-persistent |
| DT50 (lab at 20oC) | 10.5 | A5 | Non-persistent | |
| DT50 (field) | 35 | Y4 | Moderately persistent | |
| DT90 (lab at 20oC) | 69.2 | A5 | - | |
| DT90 (field) | - | - | - | |
| DT50 modelling endpoint | - | - | - | |
| Note | EU dossier lab studies DT50 range 2.6-33.3 days, DT90 range 8.5-135 days | |||
| Dissipation rate RL50 on plant matrix | Value | 18.3 | R4 | - |
| Note | Published literature RL50 range 14.9-21.4 days, fruit from 3 field crops, n=3 | |||
| Dissipation rate RL50 on and in plant matrix | Value | - | - | - |
| Note | - | |||
| Aqueous photolysis DT50 (days) at pH 7 | Value | 0.01 | A5 | Fast |
| Note | - | |||
| Aqueous hydrolysis DT50 (days) at 20oC and pH 7 | Value | 0.6 | A5 | Non-persistent |
| Note | pH sensitive: DT50 10.7 days at pH 5, 9.8 minutes at pH 9 all at 20 degC | |||
| Water-sediment DT50 (days) | 0.05 | A4 | Fast | |
| Water phase only DT50 (days) | 0.05 | A4 | Fast | |
Soil adsorption and mobility:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Linear | Kd | 86.4 | - | Slightly mobile |
| Koc | 3627 | |||
| Notes and range | EU dossier Kd range 9-157 mL/g, Koc range 1167-6004 mL/g, Soils=5 | |||
| Freundlich | Kf | - | - | - |
| Kfoc | - | |||
| 1/n | - | |||
| Notes and range | - | |||
| pH sensitivity | Not stable under wet conditions pH > 4 | |||
Other known metabolites:
| Metabolite name and reference | Aliases | Formation medium / Rate | Estimated maximum occurrence fraction | Metabolising enzymes |
| 2-amino-1,4-naphthoquinone | dithianon metabolite D33 | Rat (Faeces) | - | - |
| phthalic acid Note: Not genotoxic |
- | Soil (Photolysis, Anaerobic); Plant | - | - |
| phthadialdehdye | - | Water (Hydrolysis, Photolysis) | - | - |
| 1,2-benzenedimethanol | - | Water (Hydrolysis, Photolysis) | - | - |
| - | - | - | - | - |
| - | - | - | - | - |
| (Ref: CL 1017911) | - | Water (Hydrolysis) | - | - |
| (Ref: CL 1025) | dithianon metabolite D2 | Soil (Anaerobic) | - | - |
| (Ref: CL 153880) | dithianon metabolite D5 | Soil (Anaerobic) | 0.046 | - |
| (Ref: CL 231509) | - | Plant | - | - |
| 4,9-dioxo-4,9-dihydronaphtho(2,3-b)thiophene-2,3-dicarbonitrile (Ref: CL 902198) |
dithianon metabolite D8 | a = Rat (Faeces); b = Soil (Aerobic) | b=0.039 | - |
| (Ref: CL 902200) | dithianon metabolite D15 | Soil (Anaerobic); Plant | - | - |
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Bio-concentration factor | BCF (l kg-1) | 27 | A5 Whole fish | Low potential |
| CT50 (days) | 1 | - | ||
| Mammals - Acute oral LD50 (mg kg-1) | 300 | A5 Rat | Moderate | |
| Mammals - Short term dietary NOEL | (mg kg-1) | - | L2 Rat, 2 year | - |
| (ppm diet) | 20 | - | ||
| Birds - Acute LD50 (mg kg-1) | 309 | A5 Colinus virginianus | Moderate | |
| Birds - Short term dietary (LC50/LD50) | > 1198.5 mg kg bw-1 day-1 | A5 Colinus virginianus | - | |
| Fish - Acute 96 hour LC50 (mg l-1) | 0.07 | A5 Oncorhynchus mykiss | High | |
| Fish - Chronic 21 day NOEC (mg l-1) | 0.02 | A5 Oncorhynchus mykiss | Moderate | |
| Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) | 0.26 | A5 Daphnia magna | Moderate | |
| Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) | 0.05 | A5 Daphnia magna | Moderate | |
| Aquatic crustaceans - Acute 96 hour LC50 (mg l-1) | - | - | - | |
| Sediment dwelling organisms - Acute 96 hour LC50 (mg l-1) | > 0.5 | A5 Chironomus riparius | Moderate | |
| Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l-1) | > 0.125 | A5 Chironomus riparius | Moderate | |
| 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) | 0.09 | A5 Pseudokirchneriella subcapitata | Moderate | |
| Algae - Chronic 96 hour NOEC, growth (mg l-1) | 0.025 | A5 Pseudokirchneriella subcapitata | Moderate | |
| Honeybees (Apis spp.) | Contact acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) | > 100 | A5 | Low |
| Oral acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) | > 25.4 | A5 | Moderate | |
| Unknown mode acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) | - | - | - | |
| 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 pollinators (1) | Acute LD50 (worst case from 24 , 48 and 72 hour values - μg insect-1) | - | - | - |
| Mode of exposure | - | |||
| Other pollinators (2) | Acute LD50 (worst case from 24 , 48 and 72 hour values - μg insect-1) | - | - | - |
| Mode of exposure | - | |||
| Earthworms - Acute 14 day LC50 (mg kg-1) | 578 | A5 Eisenia foetida | Moderate | |
| Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) | 22.3 | A5 Eisenia foetida | Moderate | |
| Other soil macro-organisms - e.g. Collembola | LR50 / EC50 / NOEC / % Effect | - | - | - |
| Other arthropod (1) | LR50 g ha-1 | 6000 | >, as g product ha (Delan 70 WG: Conc 700 g/L) A5 Aphidius rhopalosiphi |
- |
| % Effect | - | - | - | |
| Other arthropod (2) | LR50 g ha-1 | 960 | as g product ha (Delan 70 WG: Conc 700 g/L) A5 Typhlodromus pyri |
- |
| % Effect | - | - | - | |
| Soil micro-organisms | Nitrogen mineralisation: No significant adverse effect Carbon mineralisation: No significant adverse effect |
A5 Dose: 14 kg ha-1, 28 days |
- | |
| Mesocosm study data | NOEAEC mg l-1 | 0.004 | A5 Fish | - |
| NOEAEC mg l-1 | - | - | - | |
HUMAN HEALTH AND PROTECTION
for dithianon
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) | 300 | A5 Rat | Moderate | |
| Mammals - Dermal LD50 (mg kg-1 body weight) | > 2000 | A5 Rat | - | |
| Mammals - Inhalation LC50 (mg l-1) | 0.31 | A5 Rat | - | |
| Other Mammal toxicity endpoints | - | - | ||
| ADI - Acceptable Daily Intake (mg kg-1bw day-1) | 0.01 | A5 Rat, SF=100 | - | |
| ARfD - Acute Reference Dose (mg kg-1bw day-1) | 0.12 | A5 Rat, SF=100 | - | |
| AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) | - | - | - | |
| AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) | 0.0135 | A5 Dog, SF=100 | - | |
| Dermal penetration studies (%) | 0.26-3.1 | A5 concentration dependent | - | |
| Dangerous Substances Directive 76/464 | - | - | - | |
| Exposure Routes | Public | No unacceptable risks to bystanders identified | ||
| Occupational | Possible risk to operators identified even with PPE Minimal risk to other workers with PPE |
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| European MRLs | Click here for the EU MRL pesticide database | |||
| Drinking Water Standards | - | - | - | |
| Drinking Water MAC (μg l-1) | 0.1 | EU Dir 89/778/EC limit; A5 | - | |
Health issues:
| Carcinogen | Genotoxic | Endocrine disrupter | Reproduction / development effects | Cholinesterase inhibitor | Neurotoxicant | |||
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A2; B2; C3; D0; E0 | - |
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| Respiratory tract irritant | Skin irritant | Skin sensitiser | Eye irritant | Phototoxicant | ||||
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| General human health issues | Toxic Possible liver and kidney toxicant May cause nausea, vomiting and diarrhea if ingested USEPA - possible human carcinogen |
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| Key: Genotoxicity A: Chromosome aberration (EFSA database) B: DNA damage/repair (EFSA database) C: Gene mutation (EFSA database) D: Genome mutation (EFSA database) E: Unspecified genotoxicity type (miscellaneous data source) 0: No data 1: Positive 2: Mixed/ambiguous results 3: Negative |
Key: Other : Yes, known to cause a problem  : No, known not to cause a problem  : Possibly, status not identified - : No data found |
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Handling issues:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
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| General |
Not explosive or oxidising IMDG Transport Code is usually 6.1 or 9 |
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| CLP classification 2013 | Health: H302 Environment: H400, H410 |
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| EC Risk Classification |
Carcinogen category 3: R40 T - Toxic: R23 Xn - Harmful: R22, R41, R43 Xi - Irritant: R66 N - Dangerous for the environment: R50, R53 |
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| EC Safety Classification |
S2, S13, S36/37/39, S45 | |||
| WHO Classification | II | - | Moderately hazardous | |
| UN Number | Variable with product, usually 3077 or 3082 | |||
| Waste disposal & packaging |
Packaging Group III (minor danger) | |||
| Language | Name |
| English | dithianon |
| French | dithianon |
| German | Dithianon |
| Danish | dithianon |
| Italian | ditianon |
| Spanish | ditianona |
| Greek | dithianon |
| Slovenian | ditianon |
| Polish | ditianon |
| Swedish | ditianon |
| Hungarian | ditianon |
| Dutch | dithianon |
Record last updated: Tuesday 25 June 2019
Contact: aeru@herts.ac.uk
© University of Hertfordshire