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.

CHEBI:24780 CHEBI:24780
CHEBI:25698 CHEBI:25698
CHEBI:35359 CHEBI:35359
CHEBI:83403 CHEBI:83403
CHEBI:83565 CHEBI:83565
CHEBI:87067 CHEBI:87067
CHEBI:87068 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

Equivalent identifiers for this same structure in other resources.

cas:68694-11-1
cas:99387-89-0
kegg.compound:C18493
pesticides:triflumizole
ppdb:665
reaxys:6960813

Activity roles

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

CHEBI:24127 CHEBI:24127
CHEBI:35718 CHEBI:35718
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
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 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 triflumizole 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:0001342`	—	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 triflumizole 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:0001342`	—	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 (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

Provenance

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