ContaminantDB: Carfentrazone-ethyl

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (8)XML

Record Information

Version

1.0

Creation Date

2013-04-25 07:56:50 UTC

Update Date

2016-11-09 01:08:58 UTC

Accession Number

CHEM002766

Identification

Common Name

Carfentrazone-ethyl

Class

Small Molecule

Description

Carfentrazone-ethyl is a contact herbicide used to control broadleaf and sedge weeds in cereals. The mode of action of carfentrazone-ethyl is the disruption of membranes by inhibiting the action of protoporphyrinogen oxidase, causing cell death. Carfentrazone is non-selective, and can be used for complete vegetation control, as well as as a desiccant and a defoliant in some crops.

Contaminant Sources

My Exposome Chemicals
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Ester
Ether
Herbicide
Organic Compound
Organochloride
Organofluoride
Pesticide
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
((14)C)Carfentrazone-ethyl	MeSH
Ethyl alpha-2-dichloro-5-(4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)-4-fluorobenzenepropanoate	MeSH

Chemical Formula

C₁₅H₁₄Cl₂F₃N₃O₃

Average Molecular Mass

412.191 g/mol

Monoisotopic Mass

411.036 g/mol

CAS Registry Number

128639-02-1

IUPAC Name

ethyl 2-chloro-3-{2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-4-fluorophenyl}propanoate

Traditional Name

carfentrazone-ethyl

SMILES

CCOC(=O)C(Cl)CC1=CC(N2N=C(C)N(C(F)F)C2=O)=C(F)C=C1Cl

InChI Identifier

InChI=1S/C15H14Cl2F3N3O3/c1-3-26-13(24)10(17)4-8-5-12(11(18)6-9(8)16)23-15(25)22(14(19)20)7(2)21-23/h5-6,10,14H,3-4H2,1-2H3

InChI Key

MLKCGVHIFJBRCD-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as phenyl-1,2,4-triazoles. These are organic compounds containing a 1,2,4-triazole substituted by a phenyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azoles

Sub Class

Triazoles

Direct Parent

Phenyl-1,2,4-triazoles

Alternative Parents

Substituents

Phenyl-1,2,4-triazole
Chlorobenzene
Fatty acid ester
Fluorobenzene
Halobenzene
Aryl chloride
Aryl fluoride
Aryl halide
Monocyclic benzene moiety
Benzenoid
Fatty acyl
Heteroaromatic compound
Alpha-halocarboxylic acid or derivatives
Alpha-halocarboxylic acid derivative
Carboxylic acid ester
Azacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Carbonyl group
Organohalogen compound
Alkyl halide
Alkyl fluoride
Alkyl chloride
Organooxygen compound
Hydrocarbon derivative
Organochloride
Organofluoride
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

organofluorine compound (CHEBI:3416 )
Pesticides (C11094 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0031 g/L	ALOGPS
logP	3.99	ALOGPS
logP	4.29	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Basic)	-7.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	62.21 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	87.74 m³·mol⁻¹	ChemAxon
Polarizability	35.55 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-004j-9234000000-7fb4e7e380bf8e0a2d43	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-0fba-0195000000-30d06b61935e7ffbdcc2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-00bc-0490000000-e386d7b27e56da4eb555	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-00kb-0009000000-afc535c3cbf8dea68646	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-03yi-0009600000-a552ec509d50ae8e0d98	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-00ou-0940000000-fafe9c790cea3eb58eb7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-00mo-0910000000-e9a8378e4d00552e1205	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-1209500000-dda3116936ad8755bc19	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9113000000-b558b0dc60e2060a28a9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-7920000000-c0d0b986c4c4c16748b4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-9000000000-08c964d8471330a35c21	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03xr-9316000000-ec86f68cc29f8bd196e8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-006x-9000000000-8ea6e2e15eef36d82df1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0003900000-ede933b8dd68d899a8db	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014j-0009000000-e6b4624f66e3500b78fe	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000f-3597000000-9239c3ed1faa2e8609bd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0022900000-b36e79db94173bb2f621	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0090000000-bc64fa22a027cc77270e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0v4j-6967000000-dd6d1596788c7cb98141	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-03ec-1429100000-3b153ce061eafe11bb29	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

LD50 (rat, oral) >5000 mg/kg LD50 (rat, dermal) >4000 mg/kg LC50 (rat, inhalation) >5.09 mg/L

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

This is a man-made compound that is used as a pesticide.

Minimum Risk Level

Not Available

Health Effects

Carfentrazone-ethyl is not considered to cause significant toxicity in helathy humans. But in patient with very large acute exposures or long-term chronic exposures, carfentrazone-ethyl may cause variegate porphyria or transient porphyria cutanea tarda-like syndrome. (1)

Symptoms

Not Available

Treatment

Remove contaminated clothing and wash skin with soap and water. For eye exposure, copious irrigation with water or saline is used. The treatment is usually symptomatic and supportive.

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0249673

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

77773

ChEBI ID

138244

PubChem Compound ID

Not Available

Kegg Compound ID

C11094

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Carfentrazone-ethyl (CHEM002766)

Structure for CHEM002766: Carfentrazone-ethyl