carpropamid

CHEBI:3434 ·resolve ·ANTIFUNGAL ·EXACT REVIEWED

A cyclopropylcarboxamide obtained by formal condensation of the carboxy group of 2,2-dichloro-1-ethyl-3-methylcyclopropanecarboxylic acid with the amino group of 1-(4-chlorophenyl)ethylamine. A rice fungicide with specific action against Pyricularia oryzae. It is not highly toxic to mammals but shows a moderate level of toxicity to birds, fish and earthworms. — ChEBI

Classification

Strictly broader compounds or drug classes this molecule belongs to.

Label unavailable CHEBI:51456
amide fungicide CHEBI:60600
Label unavailable CHEBI:83403

Chemical structure

Computed structure properties
Molecular formula	C15H18Cl3NO
Charge	0
Average mass	334.674 Da
Monoisotopic mass	333.0454 Da
Source	ChEBI
InChIKey	RXDMAYSSBPYBFW-UHFFFAOYSA-N

SMILES

CCC1(C(=O)NC(C)c2ccc(Cl)cc2)C(C)C1(Cl)Cl

InChI

InChI=1S/C15H18Cl3NO/c1-4-14(10(3)15(14,17)18)13(20)19-9(2)11-5-7-12(16)8-6-11/h5-10H,4H2,1-3H3,(H,19,20)

Also called

2,2-dichloro-N-[1-(4-chlorophenyl)ethyl]-1-ethyl-3-methylcyclopropanecarboxamide (EXACT_SYNONYM)— chebi
Carpropamid (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.

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.

fungicide CHEBI:24127
antifungal agent CHEBI:35718
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:3434`	carpropamid	`antibioticmech:chebi-c7f74a4e96`	2026-08-30

Molecular targets

The molecular entity or process this compound acts on. Each target carries evidence — this is a mechanistic claim, not a classification.

fungal scytalone dehydratase PROTEIN DIRECT_BINDING_TARGET

A 2.1-angstrom inhibitor-enzyme cocrystal directly located carpropamid in the hydrophobic cavity. The publication uses the historical organism name Pyricularia oryzae. Evidence status: PRIMARY_EVIDENCE. Source: PRIMARY_LITERATURE 1998-07 (retrieved 2026-09-02).

Magnaporthe oryzae NCBITaxon:318829

PMID:9665698 (Primary compound-enzyme cocrystal study (DOI:10.1021/bi980321b).)

Mechanism summary

Mode of action: OTHER microbial target — CURATOR: PMID:9665698 reports a 2.1-angstrom crystal structure of carpropamid bound in the hydrophobic cavity of scytalone dehydratase from the rice-blast fungus reported as Pyricularia oryzae. The enzyme participates in fungal melanin biosynthesis, so the coarse mechanism is retained as OTHER rather than mapped to an unrelated pathway enum.

Record-level evidence

PMID:9665698 (Primary structural mechanism study of the exact compound.)

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
REVIEWED 2026-09-02 · codex · LLM-assisted
Verified exact ChEBI identity, structure, and antifungal class; added a curator-owned melanin-pathway mechanism and direct scytalone-dehydratase target supported by the compound-enzyme crystal structure.
RESEEDED_FROM_SOURCES 2026-09-10 · 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 (YAML).

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