triflumizole

CHEBI:81784 ·resolve ·ANTIFUNGAL ·EXACT SEEDED

A carboxamidine resulting from the formal condensation of the amino group of 4-chloro-2-(trifluoromethyl)aniline with the oxygen of the acetyl group of N-(propoxyacetyl)imidazole. A sterol demethylation inhibitor, it is used as a fungicide for the control of powdery mildew, scab and other diseases on a variety 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

Strictly broader compounds or drug classes this molecule belongs to.

Label unavailable CHEBI:24780
Label unavailable CHEBI:25698
Label unavailable CHEBI:35359
Label unavailable CHEBI:83403
Label unavailable CHEBI:83565
conazole fungicide CHEBI:87067
imidazole fungicide CHEBI:87068

Chemical structure

Computed structure properties
Molecular formula	C15H15ClF3N3O
Charge	0
Average mass	345.752 Da
Monoisotopic mass	345.08557 Da
Source	ChEBI
InChIKey	HSMVPDGQOIQYSR-KGENOOAVSA-N

SMILES

CCCOC/C(=N\c1ccc(Cl)cc1C(F)(F)F)n1ccnc1

InChI

InChI=1S/C15H15ClF3N3O/c1-2-7-23-9-14(22-6-5-20-10-22)21-13-4-3-11(16)8-12(13)15(17,18)19/h3-6,8,10H,2,7,9H2,1H3/b21-14+

Also called

Condor (BRAND_NAME)— chebi
Procure (BRAND_NAME)— chebi
Terraguard (BRAND_NAME)— chebi
(1E)-N-[4-chloro-2-(trifluoromethyl)phenyl]-1-(1H-imidazol-1-yl)-2-propoxyethanimine (EXACT_SYNONYM)— chebi
(1E)-N-[4-chloro-2-(trifluoromethyl)phenyl]-1-(1H-imidazol-1-yl)-2-propoxyethan-1-imine (EXACT_SYNONYM)— chebi
(E)-4-chloro-α,α,α-trifluoro-N-(1-imidazol-1-yl-2-propoxyethylidene)-o-toluidine (EXACT_SYNONYM)— chebi
1-[(1E)-1-[[4-chloro-2-(trifluoromethyl)phenyl]imino]-2-propoxyethyl]-1H-imidazole (EXACT_SYNONYM)— chebi
NF-114 (EXACT_SYNONYM)— chebi
Triflumizol (EXACT_SYNONYM)— chebi
Trifumine (EXACT_SYNONYM)— chebi
[N(E)]-4-chloro-N-[1-(1H-imidazol-1-yl)-2-propoxyethylidene]-2-(trifluoromethyl)benzenamine (EXACT_SYNONYM)— chebi

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.

fungicide CHEBI:24127
antifungal agent CHEBI:35718
EC 1.14.13.70 (sterol 14α-demethylase) inhibitor CHEBI:77884
antifungal agrochemical 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
CHEBI	`CHEBI:81784`	triflumizole	`antibioticmech:chebi-faf60b50a7`	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

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

UNKNOWN 2

UNKNOWN
Determinant	ARO ID	Organism	Gene families	Evidence
CYP51 transformant(LC2-CYP51promoter(5x126bp tandem repeat)::CYP51) (transformant) [Overexpression] associated with resistance to triflumizole 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:0001342`	—	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 triflumizole 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:0001342`	—	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

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (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 2026-08-31 · 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
RESEEDED_FROM_SOURCES 2026-09-10 · seed_from_sources
Re-seeded from updated data/raw/ inventories
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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 (triflumizole) · CultureMech · NaturalProductMech · PathwayMech · TraitMech