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

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GENERAL INFORMATION

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

Introduction: 1992

EC Directive 1107/2009 (repealing 91/414):

Status	Annex 1
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
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	chlorothalonil cyproconazole difenoconazole fenpropimorph

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

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 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	-	-
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	-	-
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	-	-
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

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	LR50product ha EC50product ha NOECproduct ha % Effect	=	-	-
Other arthropod (1)	LR50 g ha-1	1000	Mortality A5 Aphidius rhopalosiphi	Harmless at 1 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
	% Effect	3.9	Mortality Dose: 0.188 kg ha-1 A5 Typhlodromus pyri	Harmless
Soil micro-organisms		Nitrogen mineralisation: No significant effect Carbon mineralisation: No significant effect	A5 Dose: 2.5 kg/ha	-
Mesocosm study data	NOEAEC mg l-1	10	A5 Daphna, Cladocera, Copepoda	-
	NOEAEC mg l-1	-	-	-

HUMAN HEALTH AND PROTECTION

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)		Not 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		Usually Packaging Group III (minor danger)

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