| Identification | More | [Name]
Azoxystrobin | [CAS]
131860-33-8 | [Synonyms]
AMISTAR
AZOXYSTROBIN
CI 23860
HERITAGE
ICI A5504
Methyl (E)-2-((6-(2-cyanophenoxy)-4-pyrimidinyl)oxy)-alpha-(methoxymethylene)benzeneacetate
pyroxystrobin
QUADRIS
methyl (E)-2-((6-(2-cyanophenoxy)-4-pyrimidinyl)oxy)-α-(methoxymethylene)benze-neacetate
methyl(E)-2-(2-(6-(2-cyanophenoxy)pyrimidin-4-yloxy)phenyl)-3-metoxyacrylate
AZOXYSTROBIN PESTANAL, 100 MG
AZOXYSTROBIN, TC 95%
Benzeneacetic acid, 2-6-(2-cyanophenoxy)-4-pyrimidinyloxy-.alpha.-(methoxymethylene)-, methyl ester, (.alpha.E)-
METHYL(E)-2-{2-[6-(2-CYANOPHENOXY)PYRIMIDIN-4-YLOXY]PHENYL}-3-METHOXYACRYLATE
Abound
Methyl (E)-2-[2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxypropenoate | [EINECS(EC#)]
204-037-5 | [Molecular Formula]
C22H17N3O5 | [MDL Number]
MFCD08277047 | [Molecular Weight]
403.39 | [MOL File]
131860-33-8.mol |
| Chemical Properties | Back Directory | [Appearance]
White to beige crystalline solid or powder. | [Melting point ]
118-119° | [Boiling point ]
581.3±50.0 °C(Predicted) | [density ]
1.33 | [vapor pressure ]
1.1 x 10-10 Pa (25 °C) | [storage temp. ]
0-6°C | [solubility ]
Chloroform: Slightly Soluble | [Colour Index ]
23860 | [form ]
neat | [pka]
-0.93±0.18(Predicted) | [Water Solubility ]
6 mg l-1 (20 °C) | [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+ | [InChIKey]
WFDXOXNFNRHQEC-GHRIWEEISA-N | [SMILES]
C1(=CC=CC=C1OC1N=CN=C(OC2=CC=CC=C2C#N)C=1)/C(=C\OC)/C(=O)OC | [LogP]
2.500 | [CAS DataBase Reference]
131860-33-8(CAS DataBase Reference) | [NIST Chemistry Reference]
Azoxystrobin(131860-33-8) | [EPA Substance Registry System]
131860-33-8(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
T;N,N,T | [Risk Statements ]
R23:Toxic by inhalation.
R50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment . | [Safety Statements ]
S22:Do not breathe dust .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S60:This material and/or its container must be disposed of as hazardous waste .
S61:Avoid release to the environment. Refer to special instructions safety data sheet . | [RIDADR ]
UN 2811 | [WGK Germany ]
2 | [Hazardous Substances Data]
131860-33-8(Hazardous Substances Data) | [Toxicity]
LD50 in rats (mg/kg): >5000 orally; >2000 dermally (Godwin) |
| Hazard Information | Back Directory | [Hazard]
Moderately toxic by inhalation.
| [Potential Exposure]
A β-methyoxyacrylate, Strobilurin is
an agricultural fungicide. | [First aid]
Move victim to fresh air. Call 911 or emergency
medical service. Give artificial respiration if victim is not
breathing. Do not use mouth-to-mouth method if victim
ingested or inhaled the substance; give artificial respiration
with the aid of a pocket mask equipped with a one-way
valve or other proper respiratory medical device.
Administer oxygen if breathing is difficult. Remove and
isolate contaminated clothing and shoes. In case of contact
with substance, immediately flush skin or eyes with running
water for at least 20 minutes. For minor skin contact,
avoid spreading material on unaffected skin. Keep victim
334 Azoxystrobin
warm and quiet. Effects of exposure (inhalation, ingestion
or skin contact) to substance may be delayed. Ensure that
medical personnel are aware of the material(s) involved
and take precautions to protect themselves. Medical observation
is recommended for 24 to 48 hours after breathing
overexposure, as pulmonary edema may be delayed. As
first aid for pulmonary edema, a doctor or authorized paramedic
may consider administering a drug or other inhalation
therapy. | [Shipping]
UN2811 Toxic solids, organic, n.o.s., Hazard
Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name
Required. UN3082 Environmentally hazardous substances,
liquid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous
hazardous material, Technical Name Required. | [Incompatibilities]
Combustible; dust may form explosive
with air. Incompatible with oxidizers (chlorates, nitrates,
peroxides, permanganates, perchlorates, chlorine, bromine,
fluorine, etc.); contact may cause fires or explosions. Keep
away from alkaline materials, strong bases, strong acids,
oxoacids, epoxides. | [Description]
Azoxystrobin is
a second broad-spectrum strobilurin fungicide (28,29).
It forms white solids with a mp = 116 ?C; vp = 1.1 ×
10?7 mPa at 25 ?C; logP = 2.5 at 20?C; water solubility =
6 mg/L; and a half-life of 11 to 17 days for aqueous
photolysis. | [Chemical Properties]
White to beige crystalline solid or powder. | [Waste Disposal]
Recycle any unused portion
of the material for its approved use or return it to the manufacturer
or supplier. Dispose of contents and container to
an approved waste disposal plant. Use a licensed professional
waste disposal service to dispose of this material.
Ultimate disposal of the chemical, product, and waste containers
must consider: the material’s impact on air quality;
potential migration in soil or water; effects on animal and
plant life; and conformance with public health, local, state,
and federal health and environmental regulations. Never
reuse or recycle used product containers unless the recycling
program specifically accepts pesticide containers and
you follow the program’s instructions for preparing the
empty containers for collection | [Uses]
Agricultural fungicide. | [Uses]
Azoxystrobin has a very broad spectrum of activity and is active
against fungal pathogens from all four taxonomic groups, the Oomycetes,
Ascomycetes, Deuteromycetes and Basidiomycetes. It controls diseases
on cereals, rice, vines, apples, peaches, bananas, citrus, curcurbits,
potatoes, tomatoes, peanuts, coffee and turf. | [Uses]
Strobilurin fungicide; inhibits mitochondrial respiration by blocking electron transfer between cytochromes b and c1. Agricultural fungicide. | [Definition]
ChEBI: An aryloxypyrimidine having a 4,6-diphenoxypyrimidine skeleton in which one of the phenyl rings is cyano-substituted at C-2 and the other carries a 2-methoxy-1-(methoxycarbonyl)vinyl substituent, also at C-2. An inhibitor of mitochondrial respiration by b
ocking electron transfer between cytochromes b and c1, it is used widely as a fungicide in agriculture. | [Agricultural Uses]
Fungicide: Azoxystrobin has been processed as a Reduced
Risk pesticide for Turf uses. Azoxystrobin is a systemic,
broad-spectrum fungicide that was first introduced in
1998. It inhibits spore germination and is used on grape
vines, cereals, potatoes, apples, bananas, citrus, tomatoes
and other crops. Largest crop uses in California are on
almonds, rice, pistachios, wine grapes, raisins and garlic.
Among the diseases it controls are rusts, downey and
powdery mildew, rice blast and apple scab. A U.S. EPA
restricted Use Pesticide (RUP) | [Trade name]
ABOUND®; AMISTAR®; AMISTAR
OPTI; AMISTAR PRO; BANKIT®; HERITAGE®;
ICIA5504 80WG®; OLYMPUS®; ORTIVA®;
PROTEGE®; PROTEGE-ALLEGIANCE WP®;PROTEGE-FL SEED APPLIED FUNGICIDE®;
QUADRIS OPTI®; QUILT®; SOYGARD WITH
PROTEGE® | [Safety Profile]
Moderately toxic by inhalation.When heated to decomposition it emits toxic vapors ofNOx. | [Metabolic pathway]
Azoxystrobin is a recently developed fungicide with a novel mode of
action (see Overview for relevant references). It was first registered in
1996. It has been and is being subjected to the full range of studies to meet
current regulatory requirements for toxicology, metabolism and
environmental fate. Information on its metabolism and environmental
fate was presented as a lecture at the 9th International Congress of
Pesticide Chemistry (IUPAC) in 1998 and this will be published in the
Proceedings. The information presented below is derived from this source
(Joseph, 1998).
Azoxystrobin is a carboxylic acid methyl ester and one of its pathways
of metabolism is via hydrolysis to its carboxylic acid. The latter is not
biologically active (see Overview) and the favourable selective toxicity of
the fungicide is due to this and other metabolic reactions in non-target
species. Azoxystrobin is readily degraded in soil and ultimately mineralised
and it is metabolised in plants and animals. Metabolism is complex
because the molecule possesses several functional groups. Five different
pathways have been identified in plants and animals. Biotransformations
occurring on the parent molecule include hydrolysis, aromatic hydroxylation,
cleavage of both phenoxy linkages, nitrile to amide hydrolysis and
fragmentation of the acrylate double bond. Some photo-induced changes
also occur, including conversion to the (Z)-isomer. | [Metabolism]
Metabolites are also rapidly degraded in soil.
Photolysis studies show a DT50 of 11 days. Due to the rapid
degradation and low soil mobility, no leaching is found in
field studies. | [storage]
Store at -20°C | [Degradation]
Azoxystrobin is degraded under conditions of aqueous photolysis with a
DT50 of 11-17 days (PM).
Soil surface photolysis of azoxystrobin (14C-labelled separately in each
of the three rings) was studied on a sandy loam for a period of 30 days.
The fungicide was degraded with a DT50 measured as a mean of the three
radiolabels, of 11 days in natural summer sunlight. The degradation was
complex, affording many initial products, all at 40% of the applied
radiocarbon. These products were themselves readily photolysed and no
product accumulated during the course of the experiment. The yield of
14CO2 in 30 days was between 17% (phenylacrylate label) and 29%
(cyanophenyl label). Thus soil surface photodegradation is likely to
be an important mechanism for the removal of azoxystrobin from the
environment. | [Toxicity evaluation]
Azoxystrobin has an acute oral LD50 > 5,000 and an
acute dermal LD50 > 2,000 mg/kg in rats. Azoxystrobin
gives only slight skin and eye irritation and is nonmutagenic
and nonteratogenic. Its NOEL is 18 mg/kg
bw/day. It has no toxicity to birds in acute studies
(LD50 > 2,000 mg/kg). It is harmless to other nontarget
organisms (honey bees, earthworms, beneficial arthropods)
due to low toxicity and rapid degradation in the
environment, which minimizes exposure. |
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