| epoxiconazole (Ref: BAS 480F) |
 |
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SUMMARY
Epoxiconazole is a broad-spectrum fungicide that has regulatory approval for use in the EU. It has a low aqueous solubility and is relatively volatile. It may persist in both soil and water systems. It is not highly toxic to mammals and is not expected to bioaccumulate. Epoxiconazole is moderately toxic to birds, honeybees, earthworms and most aquatic organisms. GENERAL INFORMATION 
for epoxiconazole
Description: A broad-spectrum fungicide for control of diseases caused by Ascomycetes, Basidiomycetes and Deuteromycetes
Example pests controlled: Black & yellow Sigatoka, Coffee rust; Septoria leaf blotch; Stem rust
Example applications: Sugarbeet; Cereals including wheat, barley, rye, oats and triticale; Coffee; Bananas
Efficacy & activity: Wheat/Eyespot=Low; Wheat/Mildew=Low; Wheat/Septoria=Moderate; Wheat/Rust=High; Wheat/Ear blight=Low; Barley/Rhynchosporium=Low; Barley/Mildew=Low; Barley/Rust=Moderate; Barley/Net blotch=Low; Barley/Ramularia=Low
Availability status: Current
Introduction & key dates: 1993, first registered
EC Regulation 1107/2009 (repealing 91/414):
| Status | Approved |
| Dossier rapporteur/co-rapporteur | UK/Poland |
| Date inclusion expires | 30/04/2020 |
| EU Candidate for substitution (CfS) | Yes - two 'Persistent-Bioaccumulative-Toxic' criteria; toxic for reproduction; endocrine disrupting properties |
| 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 | A molecule with 2 chiral centres resulting in four stereoisomers |
| Chemical formula | C17H13ClFN3O |
| Canonical SMILES | C1=CC=C(C(=C1)C2C(O2)(CN3C=NC=N3)C4=CC=C(C=C4)F)Cl |
| Isomeric SMILES | No data |
| International Chemical Identifier key (InChIKey) | FEVYAAHIKWPJNV-TYDMEHBZSA-N |
| International Chemical Identifier (InChI) | InChI=1S/C17H13ClFN3O/c18-15-4-2-1-3-14(15)16-17(23-16,9-22-11-20-10-21-22)12-5-7-13(19)8-6-12/h1-8,10-11,16H,9H2/t16-,17-/m1/s1 |
| 2D structure diagram/image available? | Yes |
General status:
| Pesticide type | Fungicide | |
| Substance group | Triazole | |
| Minimum active substance purity | 920 g/kg | |
| Known relevant impurities | EU dossier - None declared | |
| Substance origin | Synthetic | |
| Mode of action | Preventative and curative action. Sterol biosynthesis inhibitor. | |
| CAS RN | 135319-73-2 | |
| Alternative/old CAS RN | formerly 106325-08-0 | |
| EC number | 406-850-2 | |
| CIPAC number | 609 | |
| US EPA chemical code | 123909 | |
| PubChem CID | 3317081 | |
| Molecular mass (g mol-1) | 329.76 | |
| PIN (Preferred Identification Name) | rac-1-{[(2R,3S)-3-(2-chlorophenyl)-2-(4-fluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole | |
| IUPAC name | (2RS,3SR)-1-[3-(2-chlorophenyl)-2,3-epoxy-2-(4-fluorophenyl)propyl]-1H-1,2,4-triazole | |
| CAS name | rel-1-(((2R,3S)-3-(2-chlorophenyl)-2-(4-fluorophenyl)oxiranyl)methyl)-1H-1,2,4-triazole | |
| 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) | 3 | |
| Examples of recorded resistance | - | |
| Physical state | Colourless crystalline solid | |
| 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 | Buffer probably required in UK - see product label | |||
| Formulation and application details | Often supplied as a soluble concentrate which is mixed with water and applied as a spray. | |||
ENVIRONMENTAL FATE
for epoxiconazole
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Solubility - In water at 20oC (mg l-1) | 7.1 | A5 | Low | |
| Solubility - In organic solvents at 20oC (mg l-1) | 100000 | A5 - Ethyl acetate | - | |
| 140000 | A5 - Acetone | - | ||
| 28800 | C4 - Ethanol | - | ||
| 40000 | A5 - Toluene | - | ||
| Melting point (oC) | 136.7 | A5 | - | |
| Boiling point (oC) | Decomposes before boiling | A5 | - | |
| Degradation point (oC) | 310 | A5 | - | |
| Flashpoint (oC) | Not expected to self ignite; Not highly flammable | A5 | - | |
| Octanol-water partition coefficient at pH 7, 20oC | P | 2.00 X 1003 | Calculated | - |
| Log P | 3.3 | A5 | High | |
| Bulk density (g ml-1)/Specific gravity | 1.38 | A5 | - | |
| Dissociation constant (pKa) at 25oC | Not applicable | A5 | - | |
| Note: No dissociation | ||||
| Vapour pressure at 20oC (mPa) | 1.00 X 10-02 | A5 | Low volatility | |
| Henry's law constant at 25oC (Pa m3 mol-1) | 4.71 X 10-04 | A5 | Non-volatile | |
GUS leaching potential index  |
2.28 | Calculated | Transition state | |
| SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate |
Value | 1.24 X 10-01 | Calculated | - |
| Note | - | |||
| Potential for particle bound transport index |
- | Calculated | High | |
| Maximum UV-vis absorption L mol-1 cm-1 | 204nm = 32000, 263nm = 390 | A5 | - | |
| Surface tension (mN m-1) | 72.9 | A5 at 20oC, 6.4 mg l-1 | - | |
Degradation:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
General biodegradability | - |
| Soil degradation (days) (aerobic) | DT50 (typical) | 354 | B5 | Persistent |
| DT50 (lab at 20oC) | 226 | A5 | Persistent | |
| DT50 (field) | 120 | A5 | Persistent | |
| DT90 (lab at 20oC) | - | - | - | |
| DT90 (field) | - | - | - | |
| DT50 modelling endpoint | - | - | - | |
| Note | EU dossier lab studies DT50 range 98-649 days, field studies DT50 range 44-124 days; Other studies: lab DT50 range 224-2236 days, field range 52-226 days | |||
| Dissipation rate RL50 on plant matrix | Value | - | - | - |
| Note | - | |||
| Dissipation rate RL50 on and in plant matrix | Value | 11.8 | R4 | - |
| Note | Published literature RL50 range 3.1-26.5 days, 5 field crops, various matrices, n=5 | |||
| Aqueous photolysis DT50 (days) at pH 7 | Value | 52 | A5 | Stable |
| Note | - | |||
| Aqueous hydrolysis DT50 (days) at 20oC and pH 7 | Value | Stable | A5 | - |
| Note | Stable pH 5 to pH 9 at 25 degC, some hydrolysis at elevated temperatures | |||
| Water-sediment DT50 (days) | 119.8 | A5 | Slow | |
| Water phase only DT50 (days) | 65.8 | A5 | Stable | |
Soil adsorption and mobility:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Linear | Kd | - | - | - |
| Koc | - | |||
| Notes and range | - | |||
| Freundlich | Kf | 12.18 | A5 | Slightly mobile |
| Kfoc | 1073 | |||
| 1/n | 0.836 | |||
| Notes and range | EU dossier Kf range 4.79-21.78 mL/g, Kfoc range 280-2647 mL/g, 1/n range 0.766-0.910, Soils=5 | |||
| pH sensitivity | No | |||
Key metabolites:
| Metabolite | Formation medium | Estimated maximum occurrence fraction | 1107/2009 relevancy |
|
| 1,2,4-triazole (Ref: CGA 71019) | Soil | 0.066 | Minor fraction, Relevant | |
Other known metabolites:
| Metabolite name and reference | Aliases | Formation medium / Rate | Estimated maximum occurrence fraction | Metabolising enzymes |
| triazole alanine | TA | Plant | - | - |
| triazole acetic acid | - | Plant | - | - |
| triazoly hydroxyl propionic acid (Ref: 480M50) |
THPA | Plant | - | - |
| 1-(2-chlorophenyl)-2-(4-fluorophenyl)-1-hydroxy-3-(1H-1,2,4-triazol-1-yl)propane (Ref: BF480-alcohol) |
- | Soil | - | - |
| 1-[(2Z)-3-(2-chlorophenyl)-2-(4-fluorophenyl)-2 propenyl]-1H-1,2,4-triazole (Ref: BF480-entriazole) |
- | Water/sediment; Soil | - | - |
| 1H-1,2,4-triazol-1-ylacetic acid (Ref: CGA 142856) Note: Minor fraction, Relevant |
TAA | Plant | - | - |
ECOTOXICOLOGY
for epoxiconazole
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Bio-concentration factor | BCF (l kg-1) | 70 | A5 Whole fish | Low potential |
| CT50 (days) | 0.72 | - | ||
| Mammals - Acute oral LD50 (mg kg-1) | 3160 | A5 Rat | Low | |
| Mammals - Short term dietary NOEL | (mg kg-1) | 7.5 | B5 Rat | High |
| (ppm diet) | 90 | - | ||
| Birds - Acute LD50 (mg kg-1) | > 2000 | A5 Colinus virginianus | Low | |
| Birds - Short term dietary (LC50/LD50) | > 907 mg kg bw-1 day-1 | A5 Colinus virginianus | - | |
| Fish - Acute 96 hour LC50 (mg l-1) | 3.14 | A5 Oncorhynchus mykiss | Moderate | |
| Fish - Chronic 21 day NOEC (mg l-1) | 0.01 | A5 Oncorhynchus mykiss, 28 day | Moderate | |
| Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) | 8.69 | A5 Daphnia magna | Moderate | |
| Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) | 0.63 | Q2 Daphnia magna | Moderate | |
| Aquatic crustaceans - Acute 96 hour LC50 (mg l-1) | - | - | - | |
| Sediment dwelling organisms - Acute 96 hour LC50 (mg l-1) | 0.0625 | A5 Chironomus riparius, emergence | High | |
| Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l-1) | 0.0625 | A4 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) | 0.014 | A5 Lemna gibba | Moderate | |
| Non-target plants | - | - | - | |
| - | - | - | ||
| Algae - Acute 72 hour EC50, growth (mg l-1) | 1.19 | A5 Pseudokirchneriella subcapitata | Moderate | |
| Algae - Chronic 96 hour NOEC, growth (mg l-1) | 0.0078 | A5 Pseudokirchneriella subcapitata | Moderate | |
| Honeybees | Contact acute 48 hour LD50 (μg bee-1) | > 100 | A5 | Low |
| Oral acute 48 hour LD50 (μg bee-1) | > 83 | A5 | Moderate | |
| Unknown mode acute 48 hour LD50 (μg bee-1) | - | - | - | |
| Earthworms - Acute 14 day LC50 (mg kg-1) | > 500 | A5 Eisenia foetida, corr | Moderate | |
| Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) | 0.084 | A5 Esenia foetida, corr | High | |
| Other soil macro-organisms - e.g. Collembola | LR50 / EC50 / NOEC / % Effect | - | - | - |
| Other arthropod (1) | LR50 g ha-1 | 246 | >, Mortality A5 Aphidius rhopalosiphi |
- |
| % Effect | - | - | - | |
| Other arthropod (2) | LR50 g ha-1 | 258 | Mortality A5 Typhlodromus pyri |
- |
| % Effect | - | - | - | |
| Soil micro-organisms | Nitrogen mineralisation: No significant adverse effect Carbon mineralisation: No significant adverse effect |
A5 Dose: 1.88 kg ha-1 |
- | |
| Mesocosm study data | NOEAEC mg l-1 | - | - | - |
| NOEAEC mg l-1 | - | - | - | |
HUMAN HEALTH AND PROTECTION
for epoxiconazole
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) | 3160 | A5 Rat | Low | |
| Mammals - Dermal LD50 (mg kg-1 body weight) | > 2000 | A5 Rat | - | |
| Mammals - Inhalation LC50 (mg l-1) | > 5.3 | A5 Rat, 4 hr | - | |
| Other Mammal toxicity endpoints | - | - | ||
| ADI - Acceptable Daily Intake (mg kg-1bw day-1) | 0.008 | A5 Mouse, SF=100 | - | |
| ARfD - Acute Reference Dose (mg kg-1bw day-1) | 0.023 | 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) | 0.008 | A5 Rat, SF=100 | - | |
| Dermal penetration studies (%) | 50 | A5 | - | |
| Dangerous Substances Directive 76/464 | List II | - | - | |
| Exposure Limits | - | - | - | |
| Exposure Routes | Public | Acceptable risk for proposed uses | ||
| Occupational | Acceptable risk for proposed uses | |||
| 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 | Possible liver toxicant USEPA - probable human carcinogen Endocrine issues - Inhibition of aromatase activity, decrease of estrogen production |
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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 |
Not explosive or oxidising IMDG Transport Code is usually 9 |
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| CLP classification 2013 | Health: H351, H361fd Environment: H411 |
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| EC Risk Classification |
Carcinogen category 3: R40 Reproduction risk category 3: R62, R63 N - Dangerous for the environment: R51, R53 |
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| EC Safety Classification |
S2, S36/37, S46, S61 | |||
| WHO Classification | NL | - | Not listed | |
| US EPA Classification (formulation) | No consensus across products or no products available | - | - | |
| UN Number | Usually 3077 or 3082 | |||
| Waste disposal & packaging |
Packaging Group III (minor danger) | |||
TRANSLATIONS
for epoxiconazole
| Language | Name |
| English | epoxiconazole |
| French | epoxiconazole |
| German | Epoxiconazol |
| Danish | epoxiconazol |
| Italian | epossiconazolo |
| Spanish | epoxiconazol |
| Greek | epoxiconazole |
| Slovenian | epoksikonazol |
| Polish | epoksykonazol |
| Swedish | - |
| Hungarian | epoxikonazol |
| Dutch | epoxiconazool |
Record last updated: Wednesday 03 April 2019
Contact: aeru@herts.ac.uk