CHEBI:40909 - azoxystrobin

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ChEBI Name azoxystrobin
ChEBI ID CHEBI:40909
Definition 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 blocking electron transfer between cytochromes b and c1, it is used widely as a fungicide in agriculture.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C22H17N3O5
Net Charge 0
Average Mass 403.38750
Monoisotopic Mass 403.11682
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 CO\C=C(\C(=O)OC)c1ccccc1Oc1cc(Oc2ccccc2C#N)ncn1
Roles Classification
Chemical Role(s): environmental contaminant
Any minor or unwanted substance introduced into the environment that can have undesired effects.
Biological Role(s): antifungal agrochemical
Any substance used in acriculture, horticulture, forestry, etc. for its fungicidal properties.
mitochondrial cytochrome-bc1 complex inhibitor

quinone outside inhibitor
A mitochondrial cytochrome-bc1 complex inhibitor that acts at the Quinone 'outer' (Qo) binding site of the cytochrome-bc1 complex.
xenobiotic
A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
(via methoxyacrylate strobilurin antifungal agent )
(via strobilurin antifungal agent )
(via antibiotic antifungal agent )
Application(s): antifungal agrochemical
Any substance used in acriculture, horticulture, forestry, etc. for its fungicidal properties.
quinone outside inhibitor
A mitochondrial cytochrome-bc1 complex inhibitor that acts at the Quinone 'outer' (Qo) binding site of the cytochrome-bc1 complex.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing azoxystrobin (CHEBI:40909) has role antifungal agrochemical (CHEBI:86328)
azoxystrobin (CHEBI:40909) has role environmental contaminant (CHEBI:78298)
azoxystrobin (CHEBI:40909) has role mitochondrial cytochrome-bc1 complex inhibitor (CHEBI:38499)
azoxystrobin (CHEBI:40909) has role quinone outside inhibitor (CHEBI:141153)
azoxystrobin (CHEBI:40909) has role xenobiotic (CHEBI:35703)
azoxystrobin (CHEBI:40909) is a aryloxypyrimidine (CHEBI:48535)
azoxystrobin (CHEBI:40909) is a enoate ester (CHEBI:51702)
azoxystrobin (CHEBI:40909) is a enol ether (CHEBI:47985)
azoxystrobin (CHEBI:40909) is a methoxyacrylate strobilurin antifungal agent (CHEBI:86484)
azoxystrobin (CHEBI:40909) is a methyl ester (CHEBI:25248)
azoxystrobin (CHEBI:40909) is a nitrile (CHEBI:18379)
IUPAC Name
methyl (2E)-2-(2-{[6-(2-cyanophenoxy)pyrimidin-4-yl]oxy}phenyl)-3-methoxyprop-2-enoate
Synonyms Sources
E)-2-[[6-(2-cyanophenoxy)-4-pyrimidinyl]oxy]-α-(methoxymethylene) benzeneacetic acid methyl ester ChEBI
methyl (E)-2-[2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate ChEBI
Manual Xrefs Databases
54 PPDB
AZO PDBeChem
azoxystrobin Alan Wood's Pesticides
Azoxystrobin Wikipedia
C18558 KEGG COMPOUND
EP382375 Patent
US5395837 Patent
View more database links
Registry Numbers Types Sources
131860-33-8 CAS Registry Number ChemIDplus
8350244 Beilstein Registry Number Beilstein
8350244 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
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Last Modified
26 June 2018