ContaminantDB: Fenoxycarb

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (11)XML

Record Information

Version

1.0

Creation Date

2009-06-17 23:53:03 UTC

Update Date

2026-03-26 18:31:49 UTC

Accession Number

CHEM000829

Identification

Common Name

Fenoxycarb

Class

Small Molecule

Description

Fenoxycarb is a carbamate pesticide. Carbamate pesticides are derived from carbamic acid and kill insects in a similar fashion as organophosphate insecticides. They are widely used in homes, gardens and agriculture. The first carbamate, carbaryl, was introduced in 1956 and more of it has been used throughout the world than all other carbamates combined. Because of carbaryl's relatively low mammalian oral and dermal toxicity and broad control spectrum, it has had wide use in lawn and garden settings. Most of the carbamates are extremely toxic to Hymenoptera, and precautions must be taken to avoid exposure to foraging bees or parasitic wasps. Some of the carbamates are translocated within plants, making them an effective systemic treatment. (4)

Contaminant Sources

Clean Air Act Chemicals
HPV EPA Chemicals
My Exposome Chemicals
STOFF IDENT Compounds
Suspected Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amine
Carbamate
Ester
Ether
Household Toxin
Organic Compound
Pesticide
Synthetic Compound

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
(2-(4-Phenoxyphenoxy)ethyl)carbamic acid ethyl ester	ChEBI
Ethyl (2-(p-phenoxyphenoxy)ethyl)carbamate	ChEBI
Insegar	ChEBI
N-(2-(p-Phenoxyphenoxy)ethyl)carbamic acid	ChEBI
O-Ethyl N-[2-(4-phenoxyphenoxy)ethyl]carbamate	ChEBI
(2-(4-Phenoxyphenoxy)ethyl)carbamate ethyl ester	Generator
Ethyl (2-(p-phenoxyphenoxy)ethyl)carbamic acid	Generator
N-(2-(p-Phenoxyphenoxy)ethyl)carbamate	Generator
O-Ethyl N-[2-(4-phenoxyphenoxy)ethyl]carbamic acid	Generator
Ethyl(2-(4-phenoxyphenoxy)ethyl)carbamate	MeSH

Chemical Formula

C₁₇H₁₉NO₄

Average Molecular Mass

301.337 g/mol

Monoisotopic Mass

301.131 g/mol

CAS Registry Number

72490-01-8

IUPAC Name

ethyl N-[2-(4-phenoxyphenoxy)ethyl]carbamate

Traditional Name

fenoxycarb

SMILES

CCOC(=O)NCCOC1=CC=C(OC2=CC=CC=C2)C=C1

InChI Identifier

InChI=1S/C17H19NO4/c1-2-20-17(19)18-12-13-21-14-8-10-16(11-9-14)22-15-6-4-3-5-7-15/h3-11H,2,12-13H2,1H3,(H,18,19)

InChI Key

HJUFTIJOISQSKQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as diphenylethers. These are aromatic compounds containing two benzene rings linked to each other through an ether group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylethers

Direct Parent

Diphenylethers

Alternative Parents

Substituents

Diphenylether
Diaryl ether
Phenoxy compound
Phenol ether
Alkyl aryl ether
Carbamic acid ester
Carbonic acid derivative
Ether
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic nitrogen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

carbamate ester (CHEBI:5009 )
aromatic ether (CHEBI:5009 )
Carbamate insecticides (C11078 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

Chemical Roles

carbamate insecticide

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	53.5°C
Boiling Point	Not Available
Solubility	0.006 mg/mL at 20°C [SHIU,WY et al. (1990)]

Predicted Properties

Property	Value	Source
Water Solubility	0.028 g/L	ALOGPS
logP	3.52	ALOGPS
logP	3.31	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	13.93	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	56.79 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	82.53 m³·mol⁻¹	ChemAxon
Polarizability	32.18 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	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 21V, positive	splash10-066r-3960000000-bc5afa13a18369296257	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 9V, positive	splash10-0uy0-5829000000-afcd7fd69db76f3603c0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 18V, positive	splash10-000i-9420000000-36f447ee9746d0536d82	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 27V, positive	splash10-000i-9100000000-a5e95af73dea9a067915	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 36V, positive	splash10-000i-9000000000-147eae4cdf9e48755676	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 45V, positive	splash10-000i-9000000000-4b4fa148f93f05a239ea	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 54V, positive	splash10-000i-9100000000-cc0bdddf540bac94502f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT 21V, positive	splash10-000i-9410000000-35953db15ab48ac9d904	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - NA , positive	splash10-000i-9520000000-c46874e4dd0077474e91	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - NA , positive	splash10-000i-9200000000-5a7a4bb0e4aa2a1ad34e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - NA , positive	splash10-000i-9300000000-3e2c2579700f4a36eb53	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ 10V, positive	splash10-0gb9-3914000000-00ac47ca54d932061baa	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ 30V, positive	splash10-000i-9000000000-37e87ce94bcd9ebe99ef	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ 40V, positive	splash10-000i-9000000000-5a2480d45972a50be498	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ 20V, positive	splash10-000i-9100000000-70233006e3ebe5fedb2c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 10V, positive	splash10-0udi-0029000000-9167ecd750aeebf8df8f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 20V, positive	splash10-0a4i-0190000000-9aed1d0d1b0be38433db	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 30V, positive	splash10-03dr-0940000000-60fbe687ff53a26a2c84	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 40V, positive	splash10-002r-0910000000-1c28ab257b59e36931c4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0fb9-2194000000-234c124eb063aabc1e61	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004l-6290000000-6cd4763724e54924af21	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0043-6920000000-8e3c559fc04f22802151	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-4192000000-3916fedbafbd0f1f32e2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f76-9570000000-e00077b3c27eb3e1e179	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9300000000-55658a9bd9a20c813740	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Inhalation (3) ; oral (3); dermal (3)

Mechanism of Toxicity

Fenoxycarb is a cholinesterase or acetylcholinesterase (AChE) inhibitor. Carbamates form unstable complexes with chlolinesterases by carbamoylation of the active sites of the enzymes. This inhibition is reversible. A cholinesterase inhibitor suppresses the action of acetylcholine esterase. Because of its essential function, chemicals that interfere with the action of acetylcholine esterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses. Headache, salivation, nausea, vomiting, abdominal pain and diarrhea are often prominent at higher levels of exposure. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop.

Metabolism

The carbamates are hydrolyzed enzymatically by the liver; degradation products are excreted by the kidneys and the liver. (3)

Toxicity Values

LD50: >10 000 mg/kg (Oral, Rat) (5)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Spraying and application of nonarsenical insecticides entail exposures that are probably carcinogenic to humans (Group 2A). (2)

Uses/Sources

Fenoxycarb is widely used as an insecticide or pesticide in homes, gardens and agricultural applications. It is a synthetic compound.

Minimum Risk Level

Not Available

Health Effects

Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Chronically high (>10 years) exposure leads to neuropsychological consequences including disturbances in perception and visuo-motor processing (1).

Symptoms

As with organophosphates, the signs and symptoms are based on excessive cholinergic stimulation. Unlike organophosphate poisoning, carbamate poisonings tend to be of shorter duration because the inhibition of nervous tissue acetylcholinesterase is reversible, and carbamates are more rapidly metabolized. Muscle weakness, dizziness, sweating and slight body discomfort are commonly reported early symptoms. Headache, salivation, nausea, vomiting, abdominal pain and diarrhea are often prominent at higher levels of exposure. Contraction of the pupils with blurred vision, incoordination, muscle twitching and slurred speech have been reported. (4)

Treatment

If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally.

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0252212

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID