基本情報
- 標準SMILES
CNC(=O)Oc1cccc2c1OC(C)(C)O2- InChIKey
XEGGRYVFLWGFHI-UHFFFAOYSA-N- 分子式
- C11H13NO4
- 平均分子量
- 223.22 g/mol
- 単同位体質量
- 223.0844579
概要
Bendiocarb is a white solid. Melting point 265 °F (129-130 °C). Insoluble in water. Used as a contact insecticide.
名称と識別子
- 優先名称
- Bendiocarb
- IUPAC
- (2,2-dimethyl-1,3-benzodioxol-4-yl) N-methylcarbamate
- 現地名
- メチルカルバミド酸2,2-ジメチル-1,3-ベンゾジオキソール-4-イル
- 英語名
- BENDIOCARB
- 分子式
- C11H13NO4
- 分子量
- 223.23
名称と別名
名称をさらに表示
データベース識別子
- CAS
22781-23-3- PubChem CID
- 2314
- DTXSID
DTXSID9032327- ChEMBL
CHEMBL465018- ChEBI
CHEBI:34556- UNII
- QFH0ZU0A5U
- EC Number
- 245-216-8
- Nikkaji
- J3.469J
物性
構造計算による物性
- XLogP
- 1.7
- 極性表面積
- 56.8 Ų
- 水素結合供与体数
- 1
- 水素結合受容体数
- 4
- 回転可能結合数
- 2
- 重原子数
- 16
- 形式電荷
- 0
- 複雑度
- 279
実験および物理化学的性質
Pesticides
Insecticides
Active substance -> EU Pesticides database: Not approved
Pesticides -> Carbamate Insecticides
Pesticide (Bendiocarb) -> USDA PDB
Pesticide
LogP
log Kow = 1.70
1.7
Color/Form
White powder
White solid
Colorless, crystalline solid
Solubility
In water, 260 mg/L at 25 °C
200 g/kg acetone; 100 g/kg dichloromethane; 200 g/kg dioxane; 40 g/kg benzene; 10 g/kg ethanol
350 ppm in hexane
In dichloromethane 200-300, acetone 15-200, methanol 75-100, ethyl acetate 60-75, p-xylene 11.7, n-hexane 0.225 (all in g/L, 20 °C)
Solubility in kerosene 0.03%
Melting Point
129.6 °C
"265 °F"
物理化学的性質
- 融点
- 129 · 129-130°
- 沸点
- 364.51 °C · 364.51°C (rough estimate)
- 比重(密度)
- 1.25 · 1.2500
- 蒸気圧
- 4.6 x · 4.6 x 10-3 Pa (25 °C)
- 屈折率
- 1.496 · 1.4960 (estimate)
- 闪点
- 100 °C · >100 °C
- 貯蔵温度
- 0 · 0-6°C
- 溶解性
- 30 mg/ml,DMSO: · DMF: 30 mg/ml,DMSO: 30 mg/ml,DMSO:PBS (pH 7.2) (1:9): 0.1 mg/ml,Ethanol: 5 mg/ml
- 水溶解度
- 280 mg · 280 mg l-1 (20 °C)
- 酸解離定数(Pka)
- 11.98 · 11.98±0.46(Predicted)
- 外見
- 粉体・固形
- 色
- 白い
- Merck
- 13 · 13,1033
- BRN
- 1315404 · 1315404
- Henry's Law Constant
- 2.5 · 2.5×102 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
- 主な用途
- 農業環境
- InChI
- 1S/C11H13NO4/c1-11(2)15-8-6-4-5-7(9(8)16-11)14-10(13)12-3/h4-6H,1-3H3,(H,12,13)
- InChIKey
- XEGGRYVFLWGFHI-UHFFFAOYSA-N
- SMILES
- CNC(=O)Oc1cccc2OC(C)(C)Oc12
- CAS データベース
- 22781 · 22781-23-3(CAS DataBase Reference)
- NISTの化学物質情報
- Bendiocarb(22781-23-3)
- EPAの化学物質情報
- Bendiocarb (22781-23-3)
化学的性質
化学的特性Bendiocarb is an odorless, white crystalline solid. Some of the formulations of bendiocarb are classii ed as a GUP, while Turcam and its 2.5 G formulation have been classii ed as a RUP. Bendiocarb is stable under normal temperatures and pressures, but should not be mixed with alkaline preparations. Thermal decomposition products may include toxic oxides of nitrogen. It is non-corrosive. Bendiocarb as a carbamate insecticide is effective against a wide range of insects that cause nuisance and act as disease vectors. It is used to control mosquitoes, l ies, wasps, ants, l eas, cockroaches, silveri sh, ticks, and other pests in homes, industrial plants, and food storage sites. In agriculture, it is used against a vari- ety of insects, especially those in the soil. Bendiocarb is also used as a seed treatment on sugar beets and maize and against snails and slugs. Pesticides containing bendiocarb are formulated as dusts, granules, ultra-low volume sprays, and as wettable powders
安全と法規制
GHS分類
GHS Classification
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)
危険有害性情報
Regulatory Information
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.)
Hazards Summary
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.
RCRA Requirements
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
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./
Reactivity Profile
BENDIOCARB is a carbamate ester. Carbamates are chemically similar to, but more reactive than amides. Like amides they form polymers such as polyurethane resins. Carbamates are incompatible with strong acids and bases, and especially incompatible with strong reducing agents such as hydrides. Flammable gaseous hydrogen is produced by the combination of active metals or nitrides with carbamates. Strongly oxidizing acids, peroxides, and hydroperoxides are incompatible with carbamates.
DOT Emergency Guidelines
/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Health: TOXIC; may be fatal if inhaled, ingested or absorbed through skin. Inhalation or contact with some of these materials will irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution. /Carbamate pesticide, liquid, flammable, poisonous; Carbamate pesticide, liquid, flammable, toxic; Carbamate pesticide, liquid, poisonous, flammable; Carbamate pesticide, liquid, toxic, flammable/
/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion and poison hazard indoors, outdoors or in sewers. Those substances designated with a "P" may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. /Carbamate pesticide, liquid, flammable, poisonous; Carbamate pesticide, liquid, flammable, toxic; Carbamate pesticide, liquid, poisonous, flammable; Carbamate pesticide, liquid, toxic, flammable/
/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Public Safety: CALL Emergency Response Telephone Number ... As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering. /Carbamate pesticide, liquid, flammable, poisonous; Carbamate pesticide, liquid, flammable, toxic; Carbamate pesticide, liquid, poisonous, flammable; Carbamate pesticide, liquid, toxic, flammable/
/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. /Carbamate pesticide, liquid, flammable, poisonous; Carbamate pesticide, liquid, flammable, toxic; Carbamate pesticide, liquid, poisonous, flammable; Carbamate pesticide, liquid, toxic, flammable/
For more DOT Emergency Guidelines (Complete) data for BENDIOCARB (16 total), please visit the HSDB record page.
安全と保護具
Exposure Control and Personal Protection
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
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/
Cleanup Methods
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.
Disposal Methods
[40 CFR 240-280, 300-306, 702-799 (7/1/2006)] Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U278, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.
Do not contaminate ponds, ditches, or waterways with product or used containers.
Bendiocarb is stable to hydrolysis in water at pH 5; 50% decomposition (tested under EPA guidelines) occurs in 4 days at 25 °C and pH 7, the products being 2,3-isopropylidenedioxyphenol, methylamine and carbon dioxide. Recommendable method: Incineration. Peer-review: Incinerate in a unit with effluent gas scrubbing. (Peer-review conclusions of an IRPTC expert consultation (May 1985))
Preventive Measures
Aviod working in spray mist or contact with eyes, mouth, skin, and clothing. Wash hands before eating, drinking, or smoking.
If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away Keep material out of water sources and sewers. /Carbamate pesticides, solid, toxic/
If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Use water spray to knock-down vapors. /Carbamate pesticides, liquid, flammable, toxic/
If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard. Use water spray to knock-down vapors. /Carbamate pesticides, liquid, toxic, flammable/
For more Preventive Measures (Complete) data for BENDIOCARB (8 total), please visit the HSDB record page.
Threshold Limit Values (TLV)
0.1 [mg/m3], inhalable fraction and vapor
0.1 mg/m³ (inhalable fraction and vapor) [2017]
Personal Protective Equipment (PPE)
Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:
Chemical-resistant gloves. Coveralls. Face shield when handling concentrate.
Personnel protection: Wear appropriate chemical protective gloves, boots and goggles. ... Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. /Carbamate pesticides, solid, toxic/
Personnel protection: Wear appropriate chemical protective gloves, boots and goggles. ... Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. /Carbamate pesticides, liquid, flammable, toxic/
Personnel protection: Wear positive pressure self-contained breathing apparatus. ... Wear appropriate chemical protective clothing. /Carbamate pesticides, liquid, toxic, flammable/
Personnel protection: Wear positive pressure self-contained breathing apparatus. ... Wear appropriate chemical protective clothing. /Carbamate pesticides, liquid, toxic/
毒性情報
Body Burden
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
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
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
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
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).
Food Survey Values
26% of sampled wheat grains, collected from 7 areas in Saudi Arabia, contained unreported concentrations of bendiocarb(1). Bendiocarb was not detected in a 1996 market basket survey that analyzed 1,579 samples from 8 markets in 6 Egyptian governates(2).
Toxicity Summary
Bendiocarb 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.
Ecotoxicity Excerpts
/BIRDS and MAMMALS/ Bendiocarb is toxic to birds, it does not affect the reproductive performance of avian species. ...
/OTHER TERRESTRIAL SPECIES/ Routes by which nontarget predatory insects can be exposed to turfgrass pesticides include topical, residual, and dietary exposure. ...Each of these routes /was used/ to evaluate potential lethal or sublethal effects of ... bendiocarb, on survival, behavior, and fecundity of the ground beetle Harpalus pennsylvanicus DeGeer. Field-collected carabids were exposed to direct spray applications in turf plots, fed food contaminated by such applications, or exposed to irrigated or nonirrigated residues on turf cores. ... Carabids exposed to dry residues on turfgrass cores suffered high mortality from bendiocarb ... but these effects were greatly reduced by posttreatment irrigation...
/OTHER TERRESTRIAL SPECIES/ Other terrestrial species/ bendiocarb > chlorpyrifos > malathion > pyrethrins was the order of toxicity of nonthermal aerosol formulations of these insecticides to caged honeybees.
/OTHER TERRESTRIAL SPECIES/ Sexes and nymphal age classes of insecticide susceptible and resistant strains of the German cockroach, Blattella germanica, were evaluated for susceptibility to bendiocarb. Late stage nymphs had higher LC50s (ug/insect) and LD50s (ug/mg) than adult males. This reduced susceptibility to insecticides in late instar nymphs occurred irrespective of weight differences, type of insecticide, or strain of cockroach. Females had significantly higher LC50s (ug/insect) than males for bendiocarb (resistant strain). However, LD50s (ug/mg) for males and females were the same for bendiocarb (susceptible and resistant strains). Resistance ratios were 6-10 for bendiocarb in adult males and females, but ratios for 4 to 6 wk old nymphs were 53-100.
For more Ecotoxicity Excerpts (Complete) data for BENDIOCARB (6 total), please visit the HSDB record page.
Signs and 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. (L795)
法規制情報
RCRA Requirements
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
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
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).
安全データ
- wgk
- 3
- rtecs
- FC1140000
- ridadr
- 2757
- 毒性
- 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).
- hs_code
- 29329990
- risk_code
- 21-23/25-50/53
- hazard_code
- T,N
- safety_code
- 22-36/37-45-60-61
- hazard_class
- 6.1(a)
- packing_group
- II
- 毒劇物取締法
- II
- Hazard Classifications
- Acute Tox. 2 OralAcute Tox. 3 DermalAcute Tox. 3 InhalationAquatic Acute 1Aquatic Chronic 1
- ストレージクラス
- 6.1A - Combustible, acute toxic Cat. 1 and 2very toxic hazardous materials
- 有毒物質データの
- 22781-23-3(Hazardous Substances Data)
化学と産業
薬理情報
Biological Half-Life
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
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)
Absorption, Distribution and Excretion
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.
用途と製造
Uses
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/.
Formulations/Preparations
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
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.
応用分野
使用Bendiocarb 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.
一般的な説明White solid. Melting point 265°F (129-30°C). Insoluble in water. Used as a contact insecticide.
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上流原料
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