Fenoxycarb

HCID 51605

Basic information

CAS
72490-01-8
Standard SMILES
CCOC(=O)NCCOc1ccc(Oc2ccccc2)cc1
InChIKey
HJUFTIJOISQSKQ-UHFFFAOYSA-N
Molecular formula
C17H19NO4
Average molar mass
301.34 g/mol
Monoisotopic mass
301.13140809

Overview

Fenoxycarb can cause cancer according to The Environmental Protection Agency (EPA).

Names & identifiers

Preferred name
Fenoxycarb
IUPAC
ethyl N-[2-(4-phenoxyphenoxy)ethyl]carbamate
English name
Ethyl 2-(4-phenoxyphenoxy)ethylcarbamate
Molecular formula
C17H19NO4
Molecular weight
301.34

Names & synonyms

FENOXYCARB72490-01-8InsegarLogicVarikillEthyl (2-(4-phenoxyphenoxy)ethyl)carbamate79127-80-3PictylPyctylTorusethyl N-[2-(4-phenoxyphenoxy)ethyl]carbamatePHENOXYCARB
Show more names
ABG-6215FENOXYXARBComply(TM)25%FenoxycarbFenoxycarb 13C6[13C6]-FenoxycarbC13520000 Fenoxycarbfenoxycarb (ansi,bsi,iso)
Caswell No. 652CDTXSID7032393ABG 6215ECLIPSEN-(2-(p-Phenoxyphenoxy)ethyl)carbamic acid(2-(4-Phenoxyphenoxy)ethyl)carbamic acid ethyl esterJEN0LSV1G9Ethyl (2-(p-phenoxy)ethyl)carbamate

Database identifiers

CAS
72490-01-8、79127-80-3
PubChem CID
51605
DTXSID
DTXSID7032393
ChEMBL
CHEMBL15780
ChEBI
CHEBI:5009
UNII
JEN0LSV1G9
EC Number
276-696-7、683-267-1
Nikkaji
J296.319A

Properties

Computed structural properties

XLogP
4.3
Topological polar surface area
56.8 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
4
Rotatable bonds
8
Heavy atoms
22

Experimental & physicochemical properties

Pesticides · 6 items

Pesticides

Insecticides

Active substance -> EU Pesticides database: Not approved

Pesticides -> Other Insecticides

Environmental transformation -> Pesticides (parent, predecessor)

Insecticides

LogPlog Kow = 4.30
Density1.23 at 20 °C
Color/Form · 2 items

Crystals from petroleum ether

Colorless to white crystals

Solubility · 4 items

In water, 6.00 mg/L at 20 °C

Soluble in organic solvents; slightly soluble in hexane

In water, 5.76 ppm at 23 °C

In ethanol 510, acetone 770, toluene 630, n-hexane 5.3, n-octanol 130 (all in g/L, 25 °C)

CorrosivityNon-corrosive

Physicochemical properties

Melting point
53 · 53-54°
Boiling point
442.47 °C · 442.47°C (rough estimate)
Density
1.1222 · 1.1222 (rough estimate)
vapor pressure
0 Pa · 0Pa at 25℃
refractive index
1.54 · 1.5400 (estimate)
Flash point
224 °C · 224 °C

Safety & regulation

GHS classification

GHS Classification · 6 items

Warning

H351: Suspected of causing cancer [Warning Carcinogenicity]

P203, P273, P280, P318, P391, P405, and P501 (click each P-code to see the statement)

Warning

H351 (80.7%): Suspected of causing cancer [Warning Carcinogenicity]

P203, P273, P280, P318, P391, P405, and P501 (click each P-code to see the statement)

Hazard information

Regulatory Information · 5 items

Hazard Traits - Carcinogenicity

Commission Regulation (EC) No 1490/2002

2011/20/EU, Reg. (EU) 2022/801, Reg. (EU) No 540/2011

Status: Active Update: 21-02-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/32460

Fenoxycarb: HSNO Approval: HSR003370 Approved with controls

DOT LabelClass 9
Fire HazardsExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Health HazardsExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Hazards Summary · 1 item

A mild eye irritant; Liver injury occurs in high-dose animal studies; [HSDB] No evidence of effects on ruminant reproduction when used as directed in pastures or hay fields to kill fire ants; [REPROTOX] TLV Basis is liver & lung damage; [ACGIH]

Reactive GroupCarbamates

Safety & protection

Fire FightingExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
First AidExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Fire Fighting Procedures · 2 items

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.

Storage ConditionsConditions for safe storage, including any incompatibilities: Keep container tightly closed in a dry and well-ventilated place. Storage class (TRGS 510): Non Combustible Solids
Cleanup Methods · 1 item

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.

Nonfire Spill ResponseExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:

Toxicology

Treatment · 1 item

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.

Health Effects · 1 item

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 (A15321).

Ecotoxicity Values · 5 items

LC50; Species: Colinus virginianus (Northern bobwhite) juvenile; diet 11574 ppm for 8 days[USEPA, Office of Pesticide Programs; Pesticide Ecotoxicity Database (2000) on

LD50; Species: Colinus virginianus (Northern bobwhite) oral >7000 mg/kg[USEPA, Office of Pesticide Programs; Pesticide Ecotoxicity Database (2000) on

LC50; Species: Anas platyrhynchos (Mallard duck) juvenile; diet >20000 ppm for 8 days[USEPA, Office of Pesticide Programs; Pesticide Ecotoxicity Database (2000) on

LD50; Species: Anas platyrhynchos (Mallard duck) adult; oral >3000 mg/kg[USEPA, Office of Pesticide Programs; Pesticide Ecotoxicity Database (2000) on

For more Ecotoxicity Values (Complete) data for Fenoxycarb (17 total), please visit the HSDB record page.

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 4,800(SRC), determined from a structure estimation method(2), indicates that fenoxycarb is expected to have slight mobility in soil(SRC). Volatilization of fenoxycarb from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.3X10-10 atm-cu m/mole(SRC), derived from its vapor pressure, 6.5X10-9 mm Hg(3), and water solubility, 6.00 mg/L(4). Fenoxycarb is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). An aerobic degradation half-life of 6.7 hours, secondary half-life of 8.2 months, using a sandy loam soil(5) indicates that biodegradation may be an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 4,800(SRC), determined from a structure estimation method(2), indicates that fenoxycarb is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 4.3X10-10 atm-cu m/mole(SRC), derived from its vapor pressure, 6.5X10-9 mm Hg(4), and water solubility, 6.0 mg/L(5). According to a classification scheme(6), a BCF of 95(7) suggests that bioconcentration in aquatic organisms is moderate(SRC). An aerobic aquatic metabolism half-life of 3.9 days in water(7) indicates that biodegradation may be an important environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), fenoxycarb, which has a vapor pressure of 6.5X10-9 mm Hg at 25 °C(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase fenoxycarb may be removed from the air by wet or dry deposition(SRC). Fenoxycarb contains chromophores that absorb at wavelengths >290 nm(3) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Exposure RoutesInhalation (L793) ; oral (L793); dermal (L793)

Regulatory information

FIFRA Requirements · 2 items

The Agency does not expect the current risks associated with fenoxycarb use to differ from those identified during the fenoxycarb reregistration process. The existing stocks sales and distribution deadlines included in the December 30, 2010 cancellation order ensure that fenoxycarb sale, distribution, and use will decline and eventually cease entirely in the United States in the future. During the interim period, the Agency believes that existing stocks of fenoxycarb products may be used until depleted without causing unreasonable risk to human health and the environment. Pursuant to 40 CFR section 155.57 and 155.58, the Agency is issuing the Registration Review Final Decision, thus concluding the fenoxycarb registration review, for the reasons discussed above. The affected product registrations are subject to the terms and conditions of the December 30, 2010 cancellation order.

New Active Ingredients ... includes pesticide active ingredients initially registered after November 1, 1984, that currently have active product registrations. By law, these newer pesticides are not subject to the reregistration program. They must, however, meet the new safety standard of the FQPA, and will be reviewed on a 15-year cycle under the registration review program. ... Fenoxycarb is included on this list. Active Ingredient Number: 125301; Type of Pesticide: Conventional - Insecticide; Use Site: Food use, ornamentals, turf, pets; Year: 1985.

Safety data

PPE
Eyeshields, Gloves, type N95 (US)
wgk
3
rtecs
FD0423000
ridadr
UN 3077 9 / PGIII
Toxicity
LD50 in rats (mg/kg): 9220 i.p.; 16800 orally (Dorn)
risk_code
50/53

Chemistry & industry

Pharmacology

Mechanism of Action · 1 item

Fenoxycarb is an insecticide (or growth regulator) that disrupts the development of the pest. Fenoxycarb has an insect-specific mode of action exhibiting strong juvenile hormone activity. It inhibits metamorphosis to the adult stage, induces interference with the molting of early instar larvae, and produces certain ovicide and delayed larvicide adulticide effects in various insect species. ...

Metabolism/MetabolitesThe carbamates are hydrolyzed enzymatically by the liver; degradation products are excreted by the kidneys and the liver. (L793)
MeSH Pharmacological ClassificationPesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics.
Absorption, Distribution and Excretion · 2 items

About ninety percent of a dose of fenoxycarb fed to rats was excreted within 96 hours. No residues were found in the animals organs.

... Rambouillet sheep... were dosed daily with a placebo or with fenoxycarb at 0.69 or 1.38 mg/kg/day, representing ten (10x) and 20 times (20x) the maximum amounts of fenoxycarb in forage or hay treated at recommended levels for fire ant control. ... Means of hepatic fenoxycarb residues in the rams followed a statistically significant (P < or = 0.05) dose-related pattern. No fenoxycarb was detected (detection limit of 5 ppb) in any neonatal liver, despite the presence of hepatic fenoxycarb residues in the treated ewes, indicating that transplacental transport of fenoxycarb was minimal. No fenoxycarb was detected in any lamb liver at 28 days, although both the colostrum and the milk of exposed ewes were found to contain fenoxycarb at levels proportional to the treatments. ...

Uses & manufacturing

Uses · 6 items

Used as insecticide (growth regulator) for fruit, cotton, ornamentals, stored products, and public health; Also used in ant baits; [HSDB] Used for fire ant control; [Krieger, p. 414]

Farming (Pesticides) [Category: Industry]

For fenoxycarb (USEPA/OPP Pesticide Code: 125301) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Fenoxycarb is an O-ethyl carbamate ester derivative insecticide, miticide, insect growth regulator, sex attractant, or feeding stimulant. It is intended to be used to inhibit metamorphosis of juvenile insects to the adult stage.

Insect growth regulator.

Control of Lepidoptera, scale insects, and psyllids on fruit (including citrus), cotton, and ornamentals; Coleoptera and Lepidopera in stored products; and also cockroaches, fleas, mosquito larvae, and fire ants in public health situations.

Methods of ManufacturingPreparation: U. Fischer et al, European Patent Office patent 4334; eidem, United States of America patent 4215139 (1979, 1980 both to Hoffmann-La Roche).
Formulations/Preparations · 2 items

Baits, water dispersible granule, wettable powder.

Premix Partners: Lufenuron; Profenofos.

Household ProductsInformation on 1 consumer products that contain Fenoxycarb in the following categories is provided:
Use Classification · 2 items

Insecticides

Environmental transformation -> Pesticides (parent, predecessor)

General Manufacturing Information · 4 items

Registration Notes: Outside USA: Insegar in Europe.

The WHO Recommended Classification of Pesticides by Hazard identifies Fenoxycarb (technical grade) as unlikely to present an acute hazard in normal use; Main Use: insecticide.

Fenoxycarb is sold in several different formulations including dust, aerosol spray, liquid, and granular. It can be applied through shaker can, ground spreader, tank spray, aerial equipment, total release fogger, hand held spray, and chemigation. Some fenoxycarb products are packaged in water soluble packets.

In 2007, the EPA received a request from the registrant to voluntarily cancel two products, Raid DOB and Raid Flea Kill IV Plus. These products are the two remaining fenoxycarb products that are used in indoor residential settings.

Applications · 4 items

DescriptionFenoxycarb is a non-neurotoxic carbamate insecticide that acts as an insect growth regulator via juvenile hormone-like activity. It inhibits terminal development of first instar and newly transformed second instar nymphs of Florida red scale (C. aonidum) when used at a concentration of 0.0125% AI. Fenoxycarb (5 and 10 mg AI/colony) reduces the colony size index of laboratory colonies of red imported fire ants (S. invicta) by 93.6 to 95.9% at 8 weeks post-treatment. It is toxic to D. magna (LC50 = 0.5 mg a.s./L) and fish including O. mykiss, L. macrochirus, C. carpio, I. punctatus, and C. variegatus (LC50s = 0.66-1.5 mg a.s./L), but is not toxic to rats (LD50 = >10,000 mg/kg). Fenoxycarb is also an antagonist of α4β40-, α4β2-, α3β4-, and α3β2-containing rat nicotinic acetylcholine receptors (nAChRs; IC50s = 3, 2.4, 1.8, and 7.6 μM, respectively) but not rat brain acetylcholinesterase (AChE; IC50 = >1,000 μM).

UsesFenoxycarb is a carbamate insect growth regulator by preventing immature insects from reaching maturity by mimicking juvenile hormone.

UsesInsecticide.

General DescriptionWhite crystalline solid. Selective insecticide.

Suppliers25 total

杭州摩库生物医药科技有限公司+86-057181025280; +8617767106207 · [email protected]
陕西缔都化学有限公司029-029-81123119 17391733320 · [email protected]
山东洛克化工有限公司17653113209 13065062079 · [email protected]
南京生利德生物科技有限公司025-57798810 18652991625 · [email protected]
陕西麟邦实业有限公司17709134430 · [email protected]
Additional notes · 1 item

DefinitionChEBI: Fenoxycarb is a carbamate ester that is the O-ethyl carbamate of 2-(4-phenoxyphenoxy)ethylamine. It has a role as a juvenile hormone mimic, an environmental contaminant, a xenobiotic and an insecticide. It is an aromatic ether and a carbamate ester. It is functionally related to a 4-phenoxyphenol.

Related reactions

1 records

Compound notes

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