azoxystrobin

CHEBI:40909 ·resolve ·ANTIFUNGAL ·EXACT SEEDED

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. — ChEBI

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

strobilurin fungicideARO:3009305

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:18379 CHEBI:18379
CHEBI:25248 CHEBI:25248
CHEBI:47985 CHEBI:47985
CHEBI:48535 CHEBI:48535
CHEBI:51702 CHEBI:51702
CHEBI:86484 CHEBI:86484
ARO:3009305 ARO:3009305

Chemical structure

Computed structure properties
Molecular formula	C22H17N3O5
Charge	0
Average mass	403.394 Da
Monoisotopic mass	403.11682 Da
Source	ChEBI
InChIKey	WFDXOXNFNRHQEC-GHRIWEEISA-N

SMILES

CO/C=C(/C(=O)OC)c1ccccc1Oc1cc(Oc2ccccc2C#N)ncn1

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+

Also called

methyl (2E)-2-(2-{[6-(2-cyanophenoxy)pyrimidin-4-yl]oxy}phenyl)-3-methoxyprop-2-enoate (EXACT_SYNONYM)— chebi
(αE)-2-[[6-(2-cyanophenoxy)-4-pyrimidinyl]oxy]-α-(methoxymethylene) benzeneacetic acid methyl ester (EXACT_SYNONYM)— chebi
methyl (E)-2-[2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

ARO:3009185
cas:131860-33-8
kegg.compound:C18558
patent:EP382375
patent:US5395837
pdb-ccd:AZO
pesticides:azoxystrobin
ppdb:54
reaxys:8350244
wikipedia.en:Azoxystrobin
chembl:CHEMBL230001
pubchem.compound:3034285

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

CHEBI:141153 CHEBI:141153
CHEBI:35718 CHEBI:35718
CHEBI:86328 CHEBI:86328

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
ARO	`ARO:3009185`	azoxystrobin	`antibioticmech:aro-5dac57f915`	2026-08-30
CHEBI	`CHEBI:40909`	azoxystrobin	`antibioticmech:chebi-c78e11ac97`	2026-08-30

Mechanism summary

Mode of action: ENERGY_METABOLISM_INHIBITION host shared target — Assigned from ChEBI role CHEBI:141153 (quinone outside inhibitor), CHEBI:38499 (mitochondrial cytochrome-bc1 complex inhibitor). ChEBI asserts the role on the compound. The target it names is one the host has too, so the mechanism is true but is not evidence of selectivity — see mode_of_action_target_scope. Not a curator's mechanistic review.

Resistance mechanisms

11 known routes by which microbes resist this compound, grounded in ARO where CARD models them. Grouped by mechanism type — expand a group to see its determinants.

ANTIBIOTIC_TARGET_ALTERATION 6

ANTIBIOTIC_TARGET_ALTERATION
Determinant	ARO ID	Organism	Gene families	Evidence
Aspergillus fumigatus Cyp51A with mutations conferring resistance to azoxystrobin	ARO:3009545	not organism-specific	—	ARO:3009545 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3009185 (azoxystrobin); database assertion, not a primary citation.)
Aspergillus fumigatus beta-tubulin with mutations conferring resistance to azoxystrobin	ARO:3009480	not organism-specific	—	ARO:3009480 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3009185 (azoxystrobin); database assertion, not a primary citation.)
Colletotrichum gloeosporioides cytochrome b protein with mutations conferring resistance to azoxystrobin	ARO:3009275	not organism-specific	—	ARO:3009275 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3009185 (azoxystrobin); database assertion, not a primary citation.)
Colletotrichum graminicola cytochrome b protein with mutations associated with resistance to azoxystrobin	ARO:3009280	not organism-specific	—	ARO:3009280 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3009185 (azoxystrobin); database assertion, not a primary citation.)
Colletotrichum siamense beta-tubulin with mutations conferring resistance to azoxystrobin	ARO:3009471	not organism-specific	—	ARO:3009471 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3009185 (azoxystrobin); database assertion, not a primary citation.)
Colletotrichum siamense cytochrome b protein with mutations associated with resistance to azoxystrobin	ARO:3009279	not organism-specific	—	ARO:3009279 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3009185 (azoxystrobin); database assertion, not a primary citation.)

UNKNOWN 5

UNKNOWN
Determinant	ARO ID	Organism	Gene families	Evidence
Mdm10delta (deletion) associated with resistance to azoxystrobin This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism.	—	Fusarium verticillioides `NCBITaxon:117187` strain M3125 `NCBITaxon:334819` `UniProtKB:W7MZ22` `PHIPO:0000388`	—	PMID:40934067 (PHI-base primary-literature antimicrobial interaction PHIG:10867; joined to this record by exact ChEBI identifier.) Cell growth assay
Pks1delta (deletion) associated with resistance to azoxystrobin This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism.	—	Ustilaginoidea virens `NCBITaxon:1159556` strain P1 `UniProtKB:A0A8E5ME34` `PHIPO:0000388`	—	PMID:41745253 (PHI-base primary-literature antimicrobial interaction PHIG:11363; joined to this record by exact ChEBI identifier.) Cell growth assay
cytb(G143A) (amino acid mutation) [Not assayed] associated with resistance to azoxystrobin This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism.	—	Magnaporthe oryzae `NCBITaxon:318829` strain 4091-5-8 `UniProtKB:A0A089QDC9` `PHIPO:0000388`	—	PMID:12612806 (PHI-base primary-literature antimicrobial interaction PHIG:9043; joined to this record by exact ChEBI identifier.) Cell growth assay
cytb(G143S) (amino acid mutation) [Not assayed] associated with resistance to azoxystrobin This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism.	—	Magnaporthe oryzae `NCBITaxon:318829` strain 4091-5-8 `UniProtKB:A0A089QDC9` `PHIPO:0000388`	—	PMID:12612806 (PHI-base primary-literature antimicrobial interaction PHIG:9043; joined to this record by exact ChEBI identifier.) Cell growth assay
tubA(M233I) (amino acid mutation) [Not assayed] associated with resistance to azoxystrobin This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism.	—	Botrytis cinerea `NCBITaxon:40559` strain NJ11 `UniProtKB:P53373` `PHIPO:0000388`	—	PMID:26596626 (PHI-base primary-literature antimicrobial interaction PHIG:2781; joined to this record by exact ChEBI identifier.) Cell growth assay

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (ARO, CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-09-02 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-09-03 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-09-03 · seed_from_sources
Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record.