pyrifenox

CHEBI:81972 ·resolve ·ANTIFUNGAL ·EXACT SEEDED

An oxime O-ether that is the O-methyloxime of 2',4'-dichloro-2-(3-pyridyl)acetophenone. A fungicide used for control of powdery mildew, scab and other fungal pathogens on a range of crops. — 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

antibiotic without defined classificationARO:3000003

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:23697 CHEBI:23697
CHEBI:26421 CHEBI:26421
CHEBI:36816 CHEBI:36816
ARO:3000003 ARO:3000003

Chemical structure

Computed structure properties
Molecular formula	C14H12Cl2N2O
Charge	0
Average mass	295.169 Da
Monoisotopic mass	294.03267 Da
Source	ChEBI
InChIKey	CKPCAYZTYMHQEX-UHFFFAOYSA-N

SMILES

CON=C(Cc1cccnc1)c1ccc(Cl)cc1Cl

InChI

InChI=1S/C14H12Cl2N2O/c1-19-18-14(7-10-3-2-6-17-9-10)12-5-4-11(15)8-13(12)16/h2-6,8-9H,7H2,1H3

Also called

1-(2,4-Dichlorophenyl)-2-(3-pyridinyl)ethanone O-methyloxime (EXACT_SYNONYM)— chebi
2',4'-Dichloro-2-(3-pyridyl)acetophenone O-methyloxime (EXACT_SYNONYM)— chebi
Ro 15-1297 (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

ARO:3009164
cas:88283-41-4
kegg.compound:C18804
patent:NZ549922
patent:WO2004091298
pesticides:pyrifenox
ppdb:572
reaxys:8321367
pubchem.compound:55790

Activity roles

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

CHEBI:77884 CHEBI:77884
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:3009164`	pyrifenox	`antibioticmech:aro-367d12bf19`	2026-08-30
CHEBI	`CHEBI:81972`	pyrifenox	`antibioticmech:chebi-c0855d6dd6`	2026-08-30

Mechanism summary

Mode of action: ERGOSTEROL_PATHWAY_INHIBITION host shared target — Assigned from ChEBI role CHEBI:77884 (EC 1.14.13.70 (sterol 14α-demethylase) 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

2 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.

UNKNOWN 2

UNKNOWN
Determinant	ARO ID	Organism	Gene families	Evidence
CYP51 transformant(LC2-CYP51promoter(5x126bp tandem repeat)::CYP51) (transformant) [Overexpression] associated with resistance to pyrifenox This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism.	—	Penicillium digitatum `NCBITaxon:36651` strain PD5 `UniProtKB:Q9P340` `PHIPO:0001348`	—	PMID:10919801 (PHI-base primary-literature antimicrobial interaction PHIG:9164; joined to this record by exact ChEBI identifier.) Cell growth assay
CYP51+ (wild type) [Overexpression] associated with resistance to pyrifenox This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism.	—	Penicillium digitatum `NCBITaxon:36651` strain PD5 `UniProtKB:Q9P340` `PHIPO:0001348`	—	PMID:10919801 (PHI-base primary-literature antimicrobial interaction PHIG:9164; 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 2026-08-30 · 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.