| azoxystrobin (Ref: ICI 5504) |
 |
Environmental Fate - Ecotoxicology - Human Health - A to Z Index - Home
SUMMARY
Azoxystrobin is a broad-spectrum QoL fungicide that is approved for use at EU level. It has a low aqueous solubility, is non-volatile and imay leach to groundwater under certain conditions. It may be persistent in soil and can also be persistent in water systems if conditions are right. It has a low mammalian toxicity but may bioaccumulate. It is a skin and eye irritant. It is moderately toxic to birds, most aquatic life, honeybees and earthworms. GENERAL INFORMATION 
for azoxystrobin
Description: A post-emergence broad spectrum strobilurin fungicide used mainly for cereals
Example pests controlled: Rusts; Powdery mildew; Black rot; Scab; Anthracnose; White mould; Peg rot; Early & late blight; Leaf spot; Rice blast; Botrytis
Example applications: Wheat; Fruit including grapes, citrus, strawberries, peaches; Sunflowers; Vegetables including onions, brassicas and curcubits; Potatoes; Cotton; pecans; Canola; Soybeans; Peanuts; Turf; Ornamentals
Availability status: Current
Introduction & key dates: 1992
EC Regulation 1107/2009 (repealing 91/414):
| Status | Approved |
| Dossier rapporteur/co-rapporteur | UK |
| Date inclusion expires | 31/12/2021 |
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
General status:
| Pesticide type | Fungicide | |
| Substance group | Strobilurin | |
| Minimum active substance purity | 965 g/kg | |
| Known relevant impurities | EU dossier: Toluene | |
| Substance origin | Synthetic | |
| Mode of action | Systemic translaminar and protectant action having additional curative and eradicant properties. Respiration inhibitor (QoL fungicide). | |
| CAS RN | 131860-33-8 | |
| EC number | - | |
| CIPAC number | 571 | |
| US EPA chemical code | 128810 | |
| Chiral molecule | No | |
| Chemical formula | C22H17N3O5 | |
| SMILES | O=C(OC)\C(=C\OC)c3ccccc3Oc2ncnc(Oc1c(C#N)cccc1)c2 | |
| International Chemical Identifier key (InChIKey) | WFDXOXNFNRHQEC-GHRIWEEISA-N | |
| International Chemical Identifier (InChI) | InChI=1S/C22H17N3O5/c1-27-13-17(22(26)28-2)16-8-4-6-10-19(16)30-21-11-20(24-14-25-21)29-18-9-5-3-7-15(18)12-23/h3-11,13-14H,1-2H3/b17-13+ | |
| Structure diagram/image available? | Yes | |
| Molecular mass (g mol-1) | 403.4 | |
| PIN (Preferred Identification Name) | methyl (2E)-2-(2-{[6-(2-cyanophenoxy)pyrimidin-4-yl]oxy}phenyl)-3-methoxyprop-2-enoate | |
| IUPAC name | methyl (E)-2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate | |
| CAS name | methyl (αE)-2-[[6-(2-cyanophenoxy)-4-pyrimidinyl]oxy]-α-(methoxymethylene)benzeneacetate | |
| Other status information | - | |
| Herbicide Resistance Classification (HRAC) | Not applicable | |
| Herbicide Resistance Classification (WSSA) | Not applicable | |
| Insecticide Resistance Classification (IRAC) | Not applicable | |
| Fungicide Resistance Classification (FRAC) | 11 | |
| Examples of recorded resistance | - | |
| Physical state | White 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 may be required in UK - see product label | |||
| Formulation and application details | Often supplied as a suspension concentrated diluted for spray application. | |||
ENVIRONMENTAL FATE
for azoxystrobin
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Solubility - In water at 20oC (mg l-1) | 6.7 | A5 | Low | |
| Solubility - In organic solvents at 20oC (mg l-1) | 57 | A5 - Hexane | - | |
| 20000 | A5 - Methanol | - | ||
| 55000 | A5 - Toluene | - | ||
| 86000 | A5 - Acetone | - | ||
| Melting point (oC) | 116 | A5 | - | |
| Boiling point (oC) | 360 | A5 | - | |
| Degradation point (oC) | 345 | A5 | - | |
| Flashpoint (oC) | Not expected to self ignite; Not highly flammable | A5 | - | |
| Octanol-water partition coefficient at pH 7, 20oC | P | 3.16 X 1002 | Calculated | - |
| Log P | 2.5 | A5 | Low | |
| Bulk density (g ml-1)/Specific gravity | 1.34 | A5 | - | |
| Dissociation constant (pKa) at 25oC | Not applicable | A5 | - | |
| Note: No dissociation | ||||
| Vapour pressure at 25oC (mPa) | 1.10 X 10-07 | A5 | Low volatility | |
| Henry's law constant at 25oC (Pa m3 mol-1) | 7.40 X 10-09 | A5 | Non-volatile | |
| Henry's law constant at 20oC (dimensionless) | 2.72 X 10-12 | Q2 | Non-volatile | |
GUS leaching potential index  |
2.65 | Calculated | Transition state | |
| SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate |
Value | 1.98 X 10-01 | Calculated | - |
| Note | - | |||
| Potential for particle bound transport index |
- | Calculated | Medium | |
| Maximum UV-vis absorption L mol-1 cm-1 | 202.6nm = 60700, 242.7nm = 17800, 295nm = 302 | A5 | - | |
| Surface tension (mN m-1) | - | - | - | |
Degradation:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Soil degradation (days) (aerobic) | DT50 (typical) | 78 | A5 | Moderately persistent |
| DT50 (lab at 20oC) | 84.5 | A5 | Moderately persistent | |
| DT50 (field) | 180.7 | A5 | Persistent | |
| DT90 (lab at 20oC) | 363.3 | A5 | - | |
| DT90 (field) | 600.4 | A5 | - | |
| Note | EU Dossier lab studies DT50 range 35.2-248 days, DT90 range 187-824 days; Field studies DT50 range 120.9-261.9 days (actual), DT90 range 401.7-869.9 days; Other sources: 72-164 days | |||
| Plant matrix DT50 (days) | Value | 7.5 | R4 | - |
| Note | DT50 range 0.7 - 15.2 days, 14 plants/crops, various matrices | |||
| Aqueous photolysis DT50 (days) at pH 7 | Value | 8.7 | A5 | Moderately fast |
| Note | - | |||
| Aqueous hydrolysis DT50 (days) at 20oC and pH 7 | Value | Stable | A5 | - |
| Note | Not pH senstive, hydrolytically stable | |||
| Water-sediment DT50 (days) | 205 | A5 | Slow | |
| Water phase only DT50 (days) | 6.1 | A5 | Moderately fast | |
Soil adsorption and mobility:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Linear | Kd | 8.93 | A5 | Slightly mobile |
| Koc | 589 | |||
| Notes and range | EU dossier Kd range 2.1-15.0 mL/g; Koc range 304-739 mL/g, Soils=6; Other data sources: Koc = 1590 mL/g (DW3) | |||
| Freundlich | Kf | 7.35 | A5 | Moderately mobile |
| Kfoc | 423 | |||
| 1/n | 0.85 | |||
| Notes and range | EU dossier Kf range 1.5-15.0 mL/g, Kfoc range 207-594 mL/g, 1/n range 0.82-0.90, Soils=6 | |||
| pH sensitivity | No | |||
Key metabolites:
| Metabolite | Formation medium | Estimated maximum occurrence fraction | 91/414 relevancy |
|
| (E)-2-(2-(6-(2-cyanophenoxy)pyrimidin-4-yloxy)phenyl)-3-methoxyacrylic acid (Ref: R234886) |
Soil | 0.288 | Major fraction, Relevant | |
| 4-(2-cyanophenoxy)-6-hydroxypyrimidine (Ref: R401553) | Soil | 0.057 | Minor fraction, Relevant | |
| 2-(6-(2-cyanophenoxy)pyrimidin-4-yloxy)benzoic acid (Ref: R402173) | Soil | 0.076 | Minor fraction, Relevant | |
Other known metabolites:
| Metabolite name and reference | Aliases | Formation medium / Rate | Estimated maximum occurrence fraction | Metabolising enzymes |
| 2-(2-{[6-(2-cyanophenoxy)pyrimidin-4-yl]oxy}phenyl)-3-methoxypropanoic acid | Metabolite U5 | unknown | - | - |
| glucosylmalonyl 2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxypropionate | Metabolite O2 | Plant | - | - |
| glucosylmalonyl (2E)-2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate | Metabolite O3 | Plant | - | - |
| S-(2-cyano-x-hydroxyphenyl)cysteine | Metabolite L4 | Animal | - | - |
| glucosyl (E)-2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxypropionate | Metabolite N1 | Plant | - | - |
| glucosyl (2E)-2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate | Metabolite N2 | Plant | - | - |
| (2-{[6-(2-cyanophenoxy)pyrimidin-4-yl]oxy}phenyl)acetic acid | Metabolite M20 | Animal | - | - |
| 2-hydroxybenzonitrile | Metabolite M13 | unknown | - | - |
| 4-{[6-(2-cyanophenoxy)pyrimidin-4-yl]oxy}-3-[(1E)-1,3-dimethoxy-3-oxoprop-1-en-2-yl]phenyl glucopyranuronic acid | Metabolite K1 | unknown | - | - |
| 2-{[6-(2-cyanophenoxy)pyrimidin-4-yl]oxy}-x-hydroxybenzoic acid | Metabolite L9 | Animal | - | - |
| methyl (2E)-2-(2-{[6-(2-cyanophenoxy)pyrimidin-4-yl]oxy}-x-hydroxyphenyl)-3-methoxyprop-2-enoate | Metabolite L1 | Animal | - | - |
| methyl (Z)-2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (Ref: R230310) |
Metabolite M09; Z-isomer of azoxystrobin | Plant | - | - |
| 6-(2-cyanophenoxy)-3-glucosylpyrimidin-4-one (Ref: R405287) |
Metabolite M42 | Plant | - | - |
ECOTOXICOLOGY
for azoxystrobin
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Bio-concentration factor | BCF (l kg-1) | Low risk | A5 Based on LogP < 3 | Low potential |
| CT50 (days) | - | - | ||
| Mammals - Acute oral LD50 (mg kg-1) | > 5000 | A5 Rat | Low | |
| Mammals - Short term dietary NOEL | (mg kg-1) | 10 | A5 Rat | High |
| (ppm diet) | - | - | ||
| Birds - Acute LD50 (mg kg-1) | > 2000 | A5 Colinus virginianus | Low | |
| Birds - Short term dietary (LC50/LD50) | > 1179 mg kg-1 | A5 Colinus virginianus | - | |
| Fish - Acute 96 hour LC50 (mg l-1) | 0.47 | A5 Oncorhynchus mykiss | Moderate | |
| Fish - Chronic 21 day NOEC (mg l-1) | 0.147 | A5 Pimephales promelas | Moderate | |
| Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) | 0.23 | A5 Daphnia magna | Moderate | |
| Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) | 0.044 | A5 Daphnia magna | Moderate | |
| Aquatic crustaceans - Acute 96 hour LC50 (mg l-1) | 0.055 | A5 Americamysis bahia | High | |
| Sediment dwelling organisms - Acute 96 hour LC50 (mg l-1) | - | - | - | |
| Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l-1) | 0.8 | 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) | 3.2 | A5 Lemna gibba, fronds | Moderate | |
| Non-target plants | > 20 | A5 Lettuce, Radish, Wheat Seedling emergence, ER50 as mg/kg soil |
- | |
| - | - | - | ||
| Algae - Acute 72 hour EC50, growth (mg l-1) | 0.36 | A5 Pseudokirchneriella subcapitata | Moderate | |
| Algae - Chronic 96 hour NOEC, growth (mg l-1) | 0.8 | Q2 Unknown species | Moderate | |
| Honeybees | Contact acute 48 hour LD50 (μg bee-1) | > 200 | A5 | Low |
| Oral acute 48 hour LD50 (μg bee-1) | > 25 | A5 | Moderate | |
| Unknown mode acute 48 hour LD50 (μg bee-1) | - | - | - | |
| Earthworms - Acute 14 day LC50 (mg kg-1) | 283 | A5 Eisenia foetida | Moderate | |
| Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) | 20.0 | A5 Eisenia foetida | Moderate | |
| Other soil macro-organisms - e.g. Collembola | LR50 / EC50 / NOEC / % Effect | - | - | - |
| Other arthropod (1) | LR50 g ha-1 | >1000 | Mortality A5 Aphidius rhopalosiphi |
- |
| % Effect | 23.0 | Sublethal effect Dose: 0.25 kg ha-1 A5 Aphidius rhopalosiphi |
- | |
| Other arthropod (2) | LR50 g ha-1 | >1500 | Mortality A5 Typhlodromus pyri |
- |
| % Effect | 3.9 | Mortality Dose: 0.188 kg ha-1 A5 Typhlodromus pyri |
- | |
| Soil micro-organisms | Nitrogen mineralisation: No significant adverse effect Carbon mineralisation: No significant adverse effect |
A5 Dose: 2.5 kg ha-1 |
- | |
| Mesocosm study data | NOEAEC mg l-1 | 10 | A5 Daphna, Cladocera, Copepoda | - |
| NOEAEC mg l-1 | - | - | - | |
HUMAN HEALTH AND PROTECTION
for azoxystrobin
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) | 0.69 | A5 Rat (particle size <2/0 um) | - | |
| Other Mammal toxicity endpoints | - | - | ||
| ADI - Acceptable Daily Intake (mg kg-1bw day-1) | 0.2 | A5 Rat, SF=100 | - | |
| ARfD - Acute Reference Dose (mg kg-1bw day-1) | None allocated | A5 | - | |
| AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) | 0.2 | A5 Rat, SF=100 | - | |
| Dermal penetration studies (%) | 0.3-0.5 | A5 | - | |
| Dangerous Substances Directive 76/464 | - | - | - | |
| Exposure Limits | [No unacceptable risks identified] | - | - | |
| Exposure Routes | Public | - | ||
| Occupational | No unacceptable risks identified | |||
| European MRLs | Click here for the EU MRL pesticide database | |||
| 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 | Minor effects on reproduction / development observed Liver 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 |
Not explosive or oxidising IMDG Transport Code is usually 9 |
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| CLP classification 2013 | Health: H331 Environment: H400, H410 |
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| EC Risk Classification |
T - Toxic: R23 N - Dangerous for the environment: R50, R53 |
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| EC Safety Classification |
S1/2, S22, S45, S60, S61 | |||
| WHO Classification | U | - | Unlikely to present an acute hazard | |
| US EPA Classification (formulation) | No consensus across products or no products available | - | - | |
| UN Number | Variable with product, usually 2811, 3077 or 3082 | |||
| Waste disposal & packaging |
Packaging Group III (minor danger) | |||
| Language | Name |
| English | azoxystrobin |
| French | azoxystrobine |
| German | Azoxystrobin |
| Danish | azoxystrobin |
| Italian | azoxystrobin |
| Spanish | azoxiestrobina |
| Greek | azoxystrobin |
| Slovenian | azoksistrobin |
| Polish | azoksystrobina |
| Swedish | azoxystrobin |
| Hungarian | azoxistrobin |
| Dutch | azoxystrobin |
Record last updated: Wednesday 14 September 2016
Contact: aeru@herts.ac.uk