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prochloraz

CHEBI:8434 ·resolve ·ANTIFUNGAL ·EXACT SEEDED

A member of the class of ureas that is 1H-imidazole-1-carboxamide substituted by a propyl and a 2-(2,4,6-trichlorophenoxy)ethyl group at the amino nitrogen atom. A fungicide active against a wide range of diseases affecting field crops, fruit, turf and vegetables. — 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

imidazole antibioticARO:3007500

Strictly broader compounds or drug classes this molecule belongs to.

Chemical structure

Computed structure properties
Molecular formulaC15H16Cl3N3O2
Charge0
Average mass376.671 Da
Monoisotopic mass375.03081 Da
SourceChEBI
InChIKeyTVLSRXXIMLFWEO-UHFFFAOYSA-N

SMILES

CCCN(CCOc1c(Cl)cc(Cl)cc1Cl)C(=O)n1ccnc1

InChI

InChI=1S/C15H16Cl3N3O2/c1-2-4-20(15(22)21-5-3-19-10-21)6-7-23-14-12(17)8-11(16)9-13(14)18/h3,5,8-10H,2,4,6-7H2,1H3

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.

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:3009455 prochloraz antibioticmech:aro-980cd052ff 2026-08-30
CHEBI CHEBI:8434 prochloraz antibioticmech:chebi-d745c6a017 2026-08-30

Mechanism summary

Mode of action
ERGOSTEROL_PATHWAY_INHIBITION host shared target — Assigned from ChEBI role CHEBI:75282 (ergosterol biosynthesis inhibitor), 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

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

UNKNOWN 3
UNKNOWN
DeterminantARO IDOrganismGene familiesEvidence
CYP51Adelta (deletion) associated with resistance to prochloraz
This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism. Grounding review wang-2020-reference-context: Experimental background differs from the cited reference strain; unverified subject identifiers are withheld, not replaced. Reference-only source identifiers: taxon_id=NCBITaxon:690256; strain_taxon_id=NCBITaxon:1213859; protein_accession=UniProtKB:L2FQR9.		 — Colletotrichum gloeosporioides
strain JS67
PHIPO:0000528		 —
  • PMID:32569396 (PHI-base primary-literature antimicrobial interaction PHIG:734; joined to this record by exact ChEBI identifier.)
  • DOI:10.1002/ps.5964 (Identifier-scope review: Table 1, Section 2.5, Section 3.6. Reviewed 2026-10-08 by codex; curation/phibase_grounding_reviews.json SHA-256 1f5d50346b2916fce10969afa8d6409ea836dd15e8cf7fe3cfa3a78d6289b4ed.)
Cell growth assay
FgCYP51A(D243N) (amino acid mutation) [Overexpression] associated with resistance to prochloraz
This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism. Grounding review duan-2018-reference-subject-context: Source strain labels denote parental backgrounds, not exact resistant derivatives. PH-1 protein, strain TaxID and retained gene locus are reference context. Source biological fields are unchanged; no experimental accession, additional allele or MIC is inferred. Complete phenotype and compound-form review remains open. Reference-only source identifiers: strain_taxon_id=NCBITaxon:229533; protein_accession=UniProtKB:I1RJR2.		 — Fusarium graminearum NCBITaxon:5518
strain 2021 FGRAMPH1_01T14465
PHIPO:0000528		 —
  • PMID:30497711 (PHI-base primary-literature antimicrobial interaction PHIG:7751; joined to this record by exact ChEBI identifier.)
  • DOI:10.1016/j.pestbp.2018.08.011 (Identifier-scope review: Publisher-indexed primary section snippets distinguish parental strains and derived subjects; direct fetch HTTP 403 and complete Results unavailable, UniProtKB release 2026_03: I1RJR2 entry 82, sequence version 1; CYP51A locus FGRAMPH1_01T14465 and PH-1 reference taxonomy 229533. Reviewed 2026-10-08 by codex; curation/phibase_grounding_reviews.json SHA-256 1f5d50346b2916fce10969afa8d6409ea836dd15e8cf7fe3cfa3a78d6289b4ed.)
Cell growth assay
FgCYP51A(E103Q, V157L) (amino acid mutation) [Overexpression] associated with resistance to prochloraz
This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism. Grounding review duan-2018-reference-subject-context: Source strain labels denote parental backgrounds, not exact resistant derivatives. PH-1 protein, strain TaxID and retained gene locus are reference context. Source biological fields are unchanged; no experimental accession, additional allele or MIC is inferred. Complete phenotype and compound-form review remains open. Reference-only source identifiers: strain_taxon_id=NCBITaxon:229533; protein_accession=UniProtKB:I1RJR2.		 — Fusarium graminearum NCBITaxon:5518
strain BM50 FGRAMPH1_01T14465
PHIPO:0000528		 —
  • PMID:30497711 (PHI-base primary-literature antimicrobial interaction PHIG:7751; joined to this record by exact ChEBI identifier.)
  • DOI:10.1016/j.pestbp.2018.08.011 (Identifier-scope review: Publisher-indexed primary section snippets distinguish parental strains and derived subjects; direct fetch HTTP 403 and complete Results unavailable, UniProtKB release 2026_03: I1RJR2 entry 82, sequence version 1; CYP51A locus FGRAMPH1_01T14465 and PH-1 reference taxonomy 229533. Reviewed 2026-10-08 by codex; curation/phibase_grounding_reviews.json SHA-256 1f5d50346b2916fce10969afa8d6409ea836dd15e8cf7fe3cfa3a78d6289b4ed.)
Cell growth assay
ANTIBIOTIC_EFFLUX 2
ANTIBIOTIC_EFFLUX
DeterminantARO IDOrganismGene familiesEvidence
Candida glabrata CDR1 with mutations conferring resistance to prochloraz ARO:3009456 not organism-specific —
  • ARO:3009456 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3009455 (prochloraz); database assertion, not a primary citation.)
Candida glabrata Yor1 with mutations conferring resistance to prochloraz ARO:3009467 not organism-specific —
  • ARO:3009467 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3009455 (prochloraz); database assertion, not a primary citation.)
ANTIBIOTIC_TARGET_ALTERATION 2
ANTIBIOTIC_TARGET_ALTERATION
DeterminantARO IDOrganismGene familiesEvidence
Aspergillus flavus Cyp51c with mutations conferring resistance to prochloraz ARO:3009493 not organism-specific —
  • ARO:3009493 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3009455 (prochloraz); database assertion, not a primary citation.)
Candida glabrata ERG11 with mutations conferring resistance to prochloraz ARO:3009457 not organism-specific —
  • ARO:3009457 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3009455 (prochloraz); database assertion, not a primary citation.)

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 2026-08-31 · 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. REVIEWED_RESISTANCE_IDENTIFIER_SCOPE 2026-10-08 · codex · LLM-assisted

    Applied checksum-pinned PHI-base grounding review; preserved the association and experimental labels while withholding reference-only subject identifiers.

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

    Refreshed the whole-file PHI-base review checksum after an additional review; all biological fields and previous identifier-scope decisions unchanged.

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

    Refreshed the whole-file PHI-base review checksum after an additional review; all biological fields and previous identifier-scope decisions unchanged.

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

    Refreshed the whole-file PHI-base review checksum after additional reviews; all biological fields and previous identifier-scope decisions unchanged.

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

    Refreshed the whole-file PHI-base review checksum after the FKS1 review; all biological fields and previous identifier-scope decisions unchanged.

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

    Refreshed the whole-file PHI-base review checksum after two further reviews; all biological fields and previous identifier-scope decisions unchanged.

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

    Refreshed the whole-file PHI-base review checksum after Eddouzi subject reviews; all biological fields and prior decisions unchanged.

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

    Refreshed the whole-file PHI-base review checksum after Rybak reference-context reviews; all biological fields and previous decisions unchanged.

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

    Refreshed the whole-file PHI-base review checksum after carboxin reference-context reviews; all biological fields, activities and previous decisions unchanged.

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

    Refreshed the whole-file PHI-base review checksum after two additional carboxin identifier-scope corrections; all biological fields, activities and previous decisions unchanged.

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

    Refreshed the whole-file PHI-base review checksum after eleven additional identifier-scope corrections; biological fields, activities and decisions unchanged.

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

    Refreshed the whole-file PHI-base review checksum after seventeen additional identifier-scope corrections; biological fields, activities and decisions unchanged.

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

    Refreshed the whole-file PHI-base review checksum after one yeast identity-scope correction; biological fields, activities and prior decisions unchanged.

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

    Refreshed the whole-file PHI-base review checksum after twelve reference-scope corrections; biological fields, activities and prior decisions unchanged.

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

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

  23. 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.

  24. 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.

  25. 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.

  26. 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.

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

    Separated PH-1 reference identifiers from experimental parent/descendant context. Source background labels, gene, alteration, phenotype and activities preserved; no experimental accession or measurement inferred.

  28. 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.

  29. 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.

  30. 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.

  31. 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.

  32. 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.

  33. 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.

  34. 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.

  35. 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.

  36. 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.

  37. 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.

  38. 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).

Explore across X-Mech: MediaIngredientMech (prochloraz) · CultureMech · NaturalProductMech · PathwayMech · TraitMech