AntibioticMech

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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.

Chemical structure

Computed structure properties
Molecular formulaC14H12Cl2N2O
Charge0
Average mass295.169 Da
Monoisotopic mass294.03267 Da
SourceChEBI
InChIKeyCKPCAYZTYMHQEX-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

Cross-references

Identifiers for this same structure in other resources. An accession that lands on two different structures in this corpus is withheld from both rather than shown here, since it names at most one of them.

Patents and articles

Documents about this compound. A patent covers a class and an article covers a topic; neither identifies a structure.

Activity roles

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

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
SourceNative IDLabelMinted CURIEVersion
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 source-backed resistance determinants or associations, with ARO grounding where reported. Grouped by reported mechanism type.

UNKNOWN 2
UNKNOWN
DeterminantARO IDOrganismGene familiesEvidence
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. Grounding review hamamoto-2000-source-protein-context: PD5 is the parent background, not one uniquely identified tested derivative. Q9P340 links deposits from two source isolates and does not identify an exact experimental allele. Source labels and biological fields are retained; subject protein and genome remain unresolved. EC50 and MIC are distinct endpoints; no measurement is added. Reference-only source identifiers: protein_accession=UniProtKB:Q9P340.		 — Penicillium digitatum NCBITaxon:36651
strain PD5
PHIPO:0001348		 —
  • PMID:10919801 (PHI-base primary-literature antimicrobial interaction PHIG:9164; joined to this record by exact ChEBI identifier.)
  • DOI:10.1128/aem.66.8.3421-3426.2000 (Identifier-scope review: Results, Figure 4 and Table 2: separate parent, donor and tested derivatives, Nucleotide accession statement: distinct source-isolate deposits, UniProtKB release 2026_03: Q9P340 entry 120, sequence version 1; two EMBL deposit cross-references and species taxonomy. Reviewed 2026-10-08 by codex; curation/phibase_grounding_reviews.json SHA-256 1f5d50346b2916fce10969afa8d6409ea836dd15e8cf7fe3cfa3a78d6289b4ed.)
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. Grounding review hamamoto-2000-source-protein-context: PD5 is the parent background, not one uniquely identified tested derivative. Q9P340 links deposits from two source isolates and does not identify an exact experimental allele. Source labels and biological fields are retained; subject protein and genome remain unresolved. EC50 and MIC are distinct endpoints; no measurement is added. Reference-only source identifiers: protein_accession=UniProtKB:Q9P340.		 — Penicillium digitatum NCBITaxon:36651
strain PD5
PHIPO:0001348		 —
  • PMID:10919801 (PHI-base primary-literature antimicrobial interaction PHIG:9164; joined to this record by exact ChEBI identifier.)
  • DOI:10.1128/aem.66.8.3421-3426.2000 (Identifier-scope review: Results, Figure 4 and Table 2: separate parent, donor and tested derivatives, Nucleotide accession statement: distinct source-isolate deposits, UniProtKB release 2026_03: Q9P340 entry 120, sequence version 1; two EMBL deposit cross-references and species taxonomy. Reviewed 2026-10-08 by codex; curation/phibase_grounding_reviews.json SHA-256 1f5d50346b2916fce10969afa8d6409ea836dd15e8cf7fe3cfa3a78d6289b4ed.)
Cell growth assay

Curation history

  1. SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

    Seeded from data/raw/ inventories (ARO, CHEBI)

  2. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

    Re-seeded from updated data/raw/ inventories

  3. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

    Re-seeded from updated data/raw/ inventories

  4. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

    Re-seeded from updated data/raw/ inventories

  5. RESEEDED_FROM_SOURCES 2026-09-02 · seed_from_sources

    Re-seeded from updated data/raw/ inventories

  6. RESEEDED_FROM_SOURCES 2026-09-03 · seed_from_sources

    Re-seeded from updated data/raw/ inventories

  7. RESEEDED_FROM_SOURCES 2026-09-03 · seed_from_sources

    Re-seeded from updated data/raw/ inventories

  8. RESEEDED_FROM_SOURCES 2026-09-10 · seed_from_sources

    Re-seeded from updated data/raw/ inventories

  9. REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-08 · codex · LLM-assisted

    Scoped source protein and reference-strain identifiers to provenance, not exact experimental subjects, after primary-paper review. Parent labels and source biological fields preserved; no new allele, measurement or genome inferred.

  10. REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-08 · codex · LLM-assisted

    Refreshed the shared PHI-base review checksum after six identifier-scope corrections; previous decisions, biological fields and activities unchanged.

  11. REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-08 · codex · LLM-assisted

    Refreshed the shared PHI-base review checksum after eight subject-identity corrections; previous decisions, biological fields and activities unchanged.

  12. REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-08 · codex · LLM-assisted

    Refreshed shared PHI-base review checksum after the Darlington subject correction; prior review decisions, biological fields and activities unchanged.

  13. REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-08 · codex · LLM-assisted

    Refreshed shared PHI-base review checksum after the Nakayama reference-scope review; prior decisions, biological fields and activities unchanged.

  14. REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-08 · codex · LLM-assisted

    Refreshed shared PHI-base review checksum after the Duan reference-scope review; prior decisions, biological fields and activities unchanged.

  15. REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-08 · codex · LLM-assisted

    Refreshed shared PHI-base review checksum after the Piotrowska parent-reference review; prior decisions, biological fields and activities unchanged.

  16. REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-08 · codex · LLM-assisted

    Refreshed shared PHI-base review checksum after the Xu subject and species corrections; prior decisions, biological fields and activities unchanged.

  17. REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-08 · codex · LLM-assisted

    Refreshed shared PHI-base review checksum after the Shima parent-reference review; prior decisions, biological fields and activities unchanged.

  18. REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-08 · codex · LLM-assisted

    Refreshed shared PHI-base review checksum after the Mehrabi parent-reference review; prior decisions, biological fields and activities unchanged.

  19. REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-08 · codex · LLM-assisted

    Refreshed shared PHI-base review checksum after the Huang parent-reference review; prior decisions, biological fields and activities unchanged.

  20. REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-09 · codex · LLM-assisted

    Refreshed shared PHI-base review checksum after the HDF1 subject-reference review; prior decisions, biological fields and activities unchanged.

  21. REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-09 · codex · LLM-assisted

    Refreshed shared PHI-base review checksum after the Fouche parent-cohort review; prior decisions, biological fields and activities unchanged.

  22. REVIEWED_RESISTANCE_REFERENCE_CONTEXT 2026-10-09 · codex · LLM-assisted

    Refreshed shared PHI-base review checksum after the SDH8 reference-alias correction; prior decisions, biological fields and activities unchanged.

  23. REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-09 · codex · LLM-assisted

    Refreshed the shared PHI-base review checksum after the Posteraro subject-context review; previous decisions, biological fields and activities unchanged.

  24. REVIEWED_RESISTANCE_REFERENCE_CONTEXT 2026-10-12 · codex · LLM-assisted

    Refreshed the shared PHI-base review checksum after four reference-identifier scope corrections; previous decisions, biological fields and activities unchanged.

  25. REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-13 · codex · LLM-assisted

    Refreshed the shared PHI-base review checksum after one Neurospora subject-context correction; previous decisions, biological fields and activities unchanged.

Provenance

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

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