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azoxystrobin (Ref: ICI 5504)
** azoxystrobine ** ICI-A 5504 ** Icia 5504 ** Translations

Environmental Fate - Ecotoxicology - Human Health - A to Z Index - Home

GENERAL INFORMATION
for azoxystrobin

Description: A post-emergence broad spectrum strobilurin fungicide used mainly for cereals

Introduction: 1992

EC Regulation 1107/2009 (repealing 91/414):
Status Approved
Dossier rapporteur/co-rapporteur UK
Date inclusion expires 31/12/2011

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

HU

IE

IT

LT

LU

LV

MT

NL

PL

PT

RO

SE

SI

SK

UK

Also registered in: Australia, USA

General status:
Pesticide type Fungicide
Substance group Strobilurin
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 (InChI) InChI=1/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
Insecticide Resistance Classification (IRAC) Not applicable
Fungicide Resistance Classification (FRAC) 11
Physical state White crystalline solid
Related substances & organisms

Formulations:
Property Value
Example manufacturers of products using this active
  • AgriGuard
  • Clayton
  • Syngenta
Example products using this active
  • Amistar
  • Amistar Opti
  • Amistar Pro
  • Olympus
  • Priori Xtra
  • Quadris
  • Abound
  • Ortiva
UK LERAP status LERAP Category B (potatoes)
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 Non-volatile
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 2.60 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
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 Very persistent
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 - -
(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 - -
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 - -
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 Low risk A5 Based on LogP < 3 High potential
CT50 (days) - -
Bioaccumulation potential - Calculated Low
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 Moderate
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 -
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 -
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
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 - Acute 48 hour LD50 (μg bee-1) > 25 A5 Oral Moderate
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
Harmless at 1 kg ha-1
Harmless at 0.1 kg ha-1
Harmless at 0.01 kg ha-1
% Effect 23.0 Sublethal effect
Dose: 0.25 kg ha-1
A5 Aphidius rhopalosiphi
Harmless
Other arthropod (2) LR50 g ha-1 1500 Mortality
A5 Typhlodromus pyri
Harmless at 1 kg ha-1
Harmless at 0.1 kg ha-1
Harmless at 0.01 kg ha-1
% Effect 3.9 Mortality
Dose: 0.188 kg ha-1
A5 Typhlodromus pyri
Harmless
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
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
Examples of European MRLs (mg kg-1) Value Celery: 5.0; Lettuce, blackberries and raspberries: 3.0; Grapes and strawberries: 2.0; Cucumbers, summer squash, beans (with pods) and citrus: 1.0; Broccoli, cauliflowers, melons (not watermelons), pumpkins, winter squash and peas (with pods): 0.5; Brussel sprouts, cabbages, barley grains, oat grains, rye grains and wheat grains: 0.3; Beans (edible parts) and peas (edible parts): 0.2; Other vegetables, other fruit and other cereal grains: 0.05
Note Current May 2007.
For the EU pesticides database click here
Drinking Water MAC (μg l-1) - - -

Health issues:
Carcinogen Mutagen Endocrine disrupter Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant Respiratory tract irritant Skin irritant Eye irritant

-

-

-

General human health issues Minor effects on reproduction / development observed
Liver toxicant

: Yes, known to cause a problem
: No, known not to cause a problem
: Possibly, status not identified
- : No data

Handling issues:
Property Value Source/Quality Score/Other Information Interpretation
General Not explosive or oxidising
IMDG Transport Code is usually 9
CLP classification 2013 -
EC Risk Classification T - Toxic: R23
N - Dangerous for the environment: R50, R53
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)


TRANSLATIONS

for azoxystrobin

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: Saturday 28 June 2014
Contact: aeru@herts.ac.uk