Bendiocarb (ISO)

Bendiocarb

HCID 2314CAS 22781-23-3

Grundinformationen

Standard-SMILES
CNC(=O)Oc1cccc2c1OC(C)(C)O2
InChIKey
XEGGRYVFLWGFHI-UHFFFAOYSA-N
Summenformel
C11H13NO4
Durchschnittliche Molmasse
223,22 g/mol
Monoisotopische Masse
223,0844579

Überblick

Bendiocarb is a white solid. Melting point 265 °F (129-130 °C). Insoluble in water. Used as a contact insecticide.

Namen und Bezeichner

Bevorzugter Name
Bendiocarb
IUPAC
(2,2-dimethyl-1,3-benzodioxol-4-yl) N-methylcarbamate
Lokaler Name
Bendiocarb (ISO)
Englischer Name
BENDIOCARB
Summenformel
C11H13NO4
Molmasse
223.23

Namen und Synonyme

bendiocarb22781-23-3BencarbateFicamNiomilFicam WMultamatDycarbGarvoxTurcamFicam 80WFicam D
Weitere Namen anzeigen
FuamSedoxnc6897Tattoo
Ficam ULVBendiocarbamateMultimetRotateTatooSeedox 80WFisons NC 6897Bendiocarbe

Datenbank-Bezeichner

CAS
22781-23-3
PubChem CID
2314
DTXSID
DTXSID9032327
ChEMBL
CHEMBL465018
ChEBI
CHEBI:34556
UNII
QFH0ZU0A5U
EC Number
245-216-8
Nikkaji
J3.469J

Eigenschaften

Berechnete Struktureigenschaften

XLogP
1,7
Polarare Oberfläche (TPSA)
56,8 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
4
Frei drehbare Bindungen
2
Schwere Atome
16

Experimentelle und physikochemische Eigenschaften

pHVery weak acid
SpringerMaterials PropertiesFusion temperature
Pesticides · 5 Einträge

Insecticides

Active substance -> EU Pesticides database: Not approved

Pesticides -> Carbamate Insecticides

Pesticide (Bendiocarb) -> USDA PDB

Pesticide

LogP · 2 Einträge

log Kow = 1.70

1.7

OdorOdorless
Density1.25 g/cu cm at 20 °C

Physikochemische Eigenschaften

Schmelzpunkt
129 · 129-130°
Siedepunkt
364.51 °C · 364.51°C (rough estimate)
Dichte
1.25 · 1.2500
Dampfdruck
4.6 x · 4.6 x 10-3 Pa (25 °C)
Brechungsindex
1.496 · 1.4960 (estimate)
Flammpunkt
100 °C · >100 °C

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

Danger

H300: Fatal if swallowed [Danger Acute toxicity, oral]

P261, P262, P264, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P316, P321, P330, P361+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Danger

H300 (41.9%): Fatal if swallowed [Danger Acute toxicity, oral]

P261, P262, P264, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P316, P317, P321, P330, P361+P364, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Gefahrenhinweise

Regulatory Information · 3 Einträge

2002/2076

Bendiocarb: HSNO Approval: HSR003444 Approved with controls

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Other Safety InformationIMAP assessments - 1,3-Benzodioxol-4-ol, 2,2-dimethyl, methyl carbamate: Environment tier I assessment
DOT LabelPoison
Fire HazardsExcerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:
Health HazardsExcerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:
Hazards Summary · 1 Eintrag

The oral LD50 (rats) = 34-156 mg/kg. Skin absorption is the most like route of occupational exposure. [EXTOXNET] Eliminated in urine of human volunteer within 22 hours of oral dosing; Not irritating to the skin; No evidence of skin sensitization in animal testing; In a pesticide surveillance study in the UK from 2004-2012, 175 (2.6%) of the 6689 pesticide exposures involved benediocarb. None of these cases was fatal or graded as severe. [ACGIH] See CARBAMATE INSECTICIDES.

Sicherheit und Schutzausrüstung

Fire FightingExcerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:
First AidExcerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:
Exposure Control and Personal Protection · 1 Eintrag

Biological Exposure Indices (BEI) [ACGIH] - Acetylcholinesterase activity in red blood cells = 70% of individual's baseline; Butylcholinesterase activity in serum or plasma = 60% of individual's baseline; Sample at end of shift; [TLVs and BEIs]

Fire Fighting Procedures · 4 Einträge

Waterspray is preferable, but dry chemical, CO2, foam can be used.

If material on fire or involved in fire. Extinguish fire using agent suitable for type of surrounding fire (Material itself does not burn or burns with difficulty.). Use water in flooding quantities as fog. Use foam, dry chemical, or carbon dioxide. /Carbamate pesticides, solid, toxic/

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, dry chemical or carbon dioxide. /Carbamate pesticides, liquid, flammable, toxic/

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Solid streams of water may be ineffective. Use foam, dry chemical, or carbon dioxide. /Carbamate pesticides, liquid, toxic, flammable/

Storage ConditionsDo not store near food or feed. Remove or cover all food before application; protect food preparing equipment, surfaces, and eating utensils from contamination during application.
Cleanup Methods · 5 Einträge

Spillage of bendiocarb and its formulations should be removed by washing with 5% sodium hydroxide solution and then rinsing with large quantities of water.

Environmental considerations: Land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. Cover solids with a plastic sheet to prevent dissolving in rain or fire fighting water. Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ /Carbamate pesticides, solid, toxic/

Environmental considerations: Water spill: Use natural barriers or oil spill control booms to limit spill travel. Use natural deep water pockets, excavated lagoons, or sand bag barriers to trap material at bottom. Remove trapped material with suction hoses /Carbamate pesticides, solid, toxic/

Environmental considerations: Land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or commercial sorbents. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ /Carbamate pesticides, liquid, flammable, toxic/

For more Cleanup Methods (Complete) data for BENDIOCARB (12 total), please visit the HSDB record page.

Toxikologische Informationen

Body Burden · 2 Einträge

Estimated mean personal air concentrations of bendiocarb were determined for Jacksonville, Florida residents (estimated 290,000 people residing in 150,000 households) and Springfield/Chicopee, Massachusetts residents (estimated 135,000 people residing in 73,000 households) as determined by sampling over 24 hours and analysis by GCMS(1). Personal air collected from people living in Jacksonville contained bendiocarb in 14, 21, and 26% of the total samples from summer, spring, and winter sampling, respectively(2). Personal air concentrations of bendiocarb for Jacksonville residents were measured as 51.4 ng/cu m in the summer, 4.4 ng/cu m in the spring, and 3.5 ng/cu m in the winter(1). 2 and 1% of personal air samples obtained from people living in the Springfield/Chicopee, MA area in 1987 (spring sampling) and 1988 (winter sampling), respectively, contained detectable concentrations of bendiocarb (range of mean is 0.2 to 0.3 ng/cu m)(3). In a study of nine households in urban/suburban southeastern United States during August 1985, bendiocarb was detected in personal air in 3 households. The detection limit for the GC analysis was 10 ng/cu m(4).

A bendiocarb concentration of <0.2 ng/cu m was reported in personal air samples from mothers during the 32nd week of pregnancy among an inner-city cohort living in northern Manhattan or South Bronx, New York City, NY; sampling was conducted from 2001-2004(1).

Treatment · 1 Eintrag

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.

InteractionsA large number of insecticides, such as 2-sec-butylphenyl methylcarbamate, enhance the insecticidal activity and spectrum of bendiocarb, when applied as an admixture or in sequence.
Health Effects · 1 Eintrag

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 Einträge

LC50; Species: Colinus virginianus (northern bobwhite) diet 749 ppm for 8 days (95% confidence interval: 482-1162 ppm)

LD50; Species: Colinus virginianus (northern bobwhite) age 16 weeks; oral 19 mg/kg (95% confidence interval: 12-27 mg/kg)

LC50; Species: Anas platyrhynchos (Mallard duck) age 11 days; diet 477 ppm for 8 days (95% confidence interval: 228-997 ppm)

LC50; Species: Anas platyrhynchos (Mallard duck) diet 1466 ppm for 8 days (95% confidence interval: 1038-2073 ppm)

For more Ecotoxicity Values (Complete) data for BENDIOCARB (22 total), please visit the HSDB record page.

Environmental Fate · 4 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), a Koc range of 28(2) to 575(3) indicates that bendiocarb is expected to have very high to moderate mobility in soil(SRC). Volatilization of bendiocarb from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.9X10-8 atm-cu m/mole(SRC), based upon its vapor pressure, 3.45X10-5 mm Hg(4), and water solubility, 260 mg/L(4). Bendiocarb is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). Biodegradation carried out in soil showed a 48% loss within 42 days(5), suggesting that biodegradation is an important environmental fate process in soil(SRC).

TERRESTRIAL FATE: ... Bendiocarb is rapidly degraded in soil, via hydrolysis of the methyl carbamate and heterocyclic ring, followed by oxidation to polar and soil-bound residues, together with considerable mineralization of the phenyl ring to CO2. The rate of degradation of bendiocarb is pH-dependent, with slower breakdown under acidic conditions. DT50 values for the rate of decline of bendiocarb in agricultural soils and standard Speyer 2.2 range from 0.5 to 10 d, depending upon soil type, moisture and temperature. In adsorption/desorption studies, bendiocarb was hydrolyzed to 2,2-dimethyl-1,3-benzodioxol-4-ol (NC 7312). Bendiocarb and NC 7312 are weakly adsorbed (Koc 28-40); however, because it is rapidly degraded, bendiocarb should not leach. ...

AQUATIC FATE: Based on a classification scheme(1), Koc values ranging from 28(2) to 575(3) indicate that bendiocarb is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(4) based upon an estimated Henry's Law constant of 3.9X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 3.45X10-5 mm Hg(5), and water solubility, 260 mg/L(5). Hydrolysis, particularly under neutral or alkaline conditions, is expected to be a major fate process for this compound(SRC). Aqueous studies reported half-lives of 48 days, 4 days, and 45 minutes at pH values of 5, 7, and 9, respectively(6). According to a classification scheme(7), an estimated BCF of 6(SRC), from its log Kow of 1.70(8) and a regression-derived equation(9), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Photolysis half-life in water at 25 °C was 37 days(2). BOD values of 20-100% of the theoretical were reported in screening tests(10), suggesting 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), bendiocarb, which has a vapor pressure of 3.45X10-5 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase bendiocarb is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 16 hours(SRC), calculated from its rate constant of 2.4X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase bendiocarb may be removed from the air by wet or dry deposition(SRC). Bendiocarb is stable to light(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

Regulatorische Informationen

RCRA Requirements · 1 Eintrag

U278; As stipulated in 40 CFR 261.33, when bendiocarb, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

FIFRA Requirements · 3 Einträge

EPA is revoking all tolerances for residues of the insecticide ... bendiocarb ... because EPA canceled food registrations or deleted food uses from registrations following requests for voluntary cancellation or use deletion by the registrants.

... All bendiocarb products will be canceled as of December 31, 2001.

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their continued use. Under this pesticide reregistration program, EPA examines newer health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether the use of the pesticide does not pose unreasonable risk in accordance to newer safety standards, such as those described in the Food Quality Protection Act of 1996. Bendiocarb is found on List A, which contains most pesticides that are used on foods and, hence, have a high potential for human exposure. List A consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA '88. Case No: 0409; Pesticide type: insecticide; Registration Standard Date: 10/87; Case Status: OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): Bendiocarb; Data Call-in (DCI) Date(s): 03/03/95, 10/13/95; /This pesticide is no longer registered for use in the United States./

CERCLA Reportable Quantities · 1 Eintrag

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 100 lb or 45.4 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

Sicherheitsdaten

wgk
3
ridadr
2757
hs_code
29329990
RTECS-Nr.
FC1140000
risk_code
21-23/25-50/53
Toxizität
LC50 (96-hour) for rainbow trout 1.55 mg/L (Hartley and Kidd, 1987); acute oral LD50 for rats 40–156 mg/kg (Hartley and Kidd, 1987).

Chemie und Industrie

Pharmakologische Informationen

ATC CodeQP - Antiparasitic products, insecticides and repellents
Biological Half-Life · 4 Einträge

In a male volunteer given a single oral dose of 9.8 mg or approximately 0.12 mg/kg of (14)C-bendiocarb, over 99% of the administered dose was excreted in the urine in 22 hours. The plasma half-life and the half-life for renal elimination for total radioactivity was estimated at 3.5 and 3.3 hours, respectively. ...

Following an acute oral dose of (14)C-bendiocarb at 1 mg/kg body weight, plasma levels in male and female rats peaked at 10 minutes post treatment with plasma half-life being calculated at 4.4 hours for both sexes.

In a male volunteer given a single oral dose of 9.8 mg or approximately 0.12 mg/kg of (14)C-bendiocarb, over 99% of the administered dose was excreted in the urine in 22 hours. The plasma half-life and the half-life for renal elimination for total radioactivity was estimated at 3.5 and 3.3 hours, respectively. ...

Bendiocarb acts through inhibition of cholinesterase activity which is rapidly reversible, the half-life of the inhibited enzyme is approximately 30 minutes.

Metabolism/Metabolites · 6 Einträge

Metabolism ... of an oral dose of (14)C bendiocarb by a human subject was similar to the pattern observed in animals; primarily as sulfate and glucuronide conjugates of the phenol, with minor amounts of conjugated bendiocarb and N-hydroxymethyl bendiocarb.

In all species examined, bendiocarb was metabolized via cleavage of the carbamate ester group to yield the phenol (2,2-dimethyl-1,3-benzoxodiol-4-ol), which was excreted as sulfate and glucuronide conjugates.

Spontaneous hydrolysis of the carbamate-cholinesterase complex occurs in vivo, leading to the disappearance of clinical effects within 24 hr. /Carbamate pesticides/

Bendiocarb is readily conjugated and metabolized by liver microsome enzymes, it is rapidly excreted, mainly as sulfate and beta-glucuronide conjugates of the phenol derivative.

For more Metabolism/Metabolites (Complete) data for BENDIOCARB (11 total), please visit the HSDB record page.

The 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 · 5 Einträge

In rats given a 1 mg/kg oral dose of (14)C bendiocarb, plasma levels of radioactivity peaked at 10 min after administration. Following a 2.5 mg/kg dose, radioactivity in the tissues 72 hr after administration ranged from 0.015 to 0.061 ppm (as bendiocarb). Six days after 10 day dietary administration of ring-labeled bendiocarb to rats ended, residues were detected in the fat, liver, kidneys, muscle, and brain, the levels being highest in the fat tissue. ... Within 2 days after oral administration of ring-labeled bendiocarb (at 0.125-10 mg/kg) to rats, 89-90% of the dose was eliminated in the urine, 2-6% in the expired air, and 2-6% in the feces. ...

In rats and a range of other mammals, rapidly absorbed following oral admin or inhalation, but not following skin contact. Rapidly detoxified and eliminated almost completely within 24 hr as the sulfate and glucuronide conjugate of the principal metabolite, 2,2-dimethyl-1,3-benzodioxol-4-ol.

Bendiocarb may be absorbed from the gastrointestinal tract or to a limited extent through the intact skin. Low vapor pressure makes inhalation unlikely except from airborne spray mist.

Male and female rats treated with a single oral dose of (14)C-bendiocarb at approximately 10 mg/kg body weight eliminated over 95% of the administered radioactivity in urine (89%), expired air (6%) and feces (2%) within 2 days of dosing. There was no significant sex different in rate and route of elimination.

For more Absorption, Distribution and Excretion (Complete) data for BENDIOCARB (7 total), please visit the HSDB record page.

Verwendung und Herstellung

Uses · 6 Einträge

Used as a carbamate insecticide in homes and industries; also used in seed treatment; Most formulations are for general use, but Turcam and Turcam 2.5G are Restricted Use Pesticides. [EXTOXNET] Has been used to protect crops and in homes to kill mosquitoes and household pests; [ACGIH]

Voluntarily cancelled as of December 31, 2001; [Reference #2]

Farming (Pesticides) [Category: Industry]

For Bendiocarb (USEPA/OPP Pesticide Code: 105201) 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./ /Former use in the USA for all uses/

End use products used in or around the home can be sold or distributed by the registrant until October 31, 2000. All bendiocarb products will be canceled as of December 31, 2001 /Former use in the USA for all uses/ /Former use in the USA for all uses/.

To control cockroaches, other household pests, and soil insects /Former use in the USA for all uses/.

Methods of ManufacturingProduced by the reaction of 2,3-isopropylidenedioxyphenol with methyl isocyanate ... .
Formulations/Preparations · 3 Einträge

Formulations include wettable powders, a dust, granules, and a solution for ultralow-volume application.

Aerosol dispenser; dispersible powder; flowable concentrate for seed treatment; granule; suspension concentrate; ultra-low volume suspension; wettable powder

Mixtures (bendiocarb +): piperonyl butoxide + pyrethrins

General Manufacturing Information · 5 Einträge

The WHO Recommended Classification of Pesticides by Hazard identifies bendiocarb (technical grade) as Class II: moderately hazardous; Main Use: insecticide.

It was introduced in 1971 by Fisons LTD Agrochemical Division ... protected by British patent 1220056.

Ficam ULV has been registered for mosquito control in cold ULV ground applications only. Has been listed by FAO for ground and aerial control of grasshoppers and locusts.

BENDIOCARB WAS FOUND TO HAVE MOLLUSCICIDAL ACTIVITY.

For more General Manufacturing Information (Complete) data for BENDIOCARB (7 total), please visit the HSDB record page.

Anwendungen · 1 Eintrag

VerwendenBendiocarb is a benzodioxolyl carbamate derivative. Bendiocarb is commonly used as an insecticide in agriculture against a wide range of pests and insects. Bendiocarb is one of the insecticides recomm ended by world health organization (WHO) for use in malaria control.

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