Bendiocarb
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Bendiocarb
structure -
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CAS No:
22781-23-3
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Formula:
C11H13NO4
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Chemical Name:
Bendiocarb
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Synonyms:
1,3-Benzodioxol-4-ol,2,2-dimethyl-,4-(N-methylcarbamate);Carbamic acid,methyl-,2,3-(isopropylidenedioxy)phenyl ester;1,3-Benzodioxol-4-ol,2,2-dimethyl-,methylcarbamate;Phenol,2,3-(isopropylidenedioxy)-,methylcarbamate;NC 6897;Fisons NC 6897;Bendiocarb;Ficam;Ficam 80W;2,2-Dimethyl-1,3-benzodioxol-4-yl N-methylcarbamate;2,2-Dimethyl-1,3-benzodioxol-4-yl methylcarbamate;Ficam W;Garvox;Niomil;Bencarbate;Tatoo;Seedox;Seedox 80W;Seedox (insecticide);Turcam;Tattoo;Dycarb;Multamat;61533-57-1
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CAS No:
Description
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
Bendiocarb is a white solid. Melting point 265°F (129-130°C). Insoluble in water. Used as a contact insecticide.|White solid.
Bendiocarb is a white solid. Melting point 265°F (129-130°C). Insoluble in water. Used as a contact insecticide.|Bendiocarb is a carbamate ester and a member of benzodioxoles. It has a role as an EC 3.1.1.7 (acetylcholinesterase) inhibitor, a carbamate insecticide and an agrochemical. It derives from a methylcarbamic acid.
Bendiocarb Basic Attributes
223.23
223.23
245-216-8
QFH0ZU0A5U
2757
DTXSID9032327
White powder|White solid|Colorless, crystalline solid
2932999012
Characteristics
56.8
1.70
White Powder/Solid
0.69 g/cm3 @ Temp: 20 °C
129-130 °C
298.8±40.0 °C at 760 mmHg
>100 °C
1.523
Solubility in kerosene 0.03%
0-6°C
4.6 x 10 -3 Pa (25 °C)
1.25
Oral-rat LD50: 40 mg/kg; Oral-Mouse LD50: 45 mg/kg
Thermal decomposition of toxic nitrogen oxide gas
Odorless
Henry's Law constant = 3.9X10-8 atm-cu m/mol at 25 °C (est)
PARTITION RATIO AT 20 °C IS 1:9 FOR WATER/HEXANE|Hydrolyzes rapidly in alkaline media and decomposes above 125 °C. Stable to light.|Hydrolyzed rapidly in alkaline media, and more slowly in neutral and acidic media (25 °C), 2 days (pH 7), the products being 2,2-dimethyl-1,3-benzodioxol-4-ol, methylamine and carbon dioxide. Stable to light an heat.|Hydroxyl radical reaction rate constant = 2.39X10-11 cu cm/molec-sec at 25 °C (est)
Insoluble in water.
Carbamates
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.
Lack of corrosive properties
318 J/g at 25 °C
Safety Information
II
6.1(a)
2757
3
21-23/25-50/53
22-36/37-45-60-61
FC1140000
T,N
The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials
Formulated material (80%) is stable at temperatures below 40 deg C. In aqueous solution at 25 deg C the half-life is 48 days at ph 5; 81 hours at ph 7; and 45 minutes at ph 9. Under ph 5 bendiocarb slowly degrades to pyrogallol and acetone. On non-absorptive surfaces and at low humidity it resists oxidation. It undergoes photo-oxidation in direct sunlight.
P261-P273-P280-P301 + P310-P311-P501
H301-H312-H331-H410
[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))
USEPA/OPPTS; R.E.D. Facts: Bendiocarb p.5 EPA 738-F-99-010 (Sept 1999)
Excerpt from ERG Guide 151 [Substances - Toxic (Non-combustible)]: Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Containers may explode when heated. Runoff may pollute waterways. (ERG, 2016)
|Danger|H300: Fatal if swallowed [Danger Acute toxicity, oral]|P261, P264, P270, P271, P273, P280, P301+P310, P302+P352, P304+P340, P311, P312, P321, P322, P330, P361, P363, P391, P403+P233, P405, and P501|H300 (78%): Fatal if swallowed [Danger Acute toxicity, oral]|Aggregated GHS information provided by 200 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P260, P262, P264, P270, P280, P301+P310, P302+P350, P305+P351+P338, P309+P311, P310, P321, P322, P330, P337+P313, P361, P363, P405, and P501
Excerpt from ERG Guide 151 [Substances - Toxic (Non-combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)
Excerpt from ERG Guide 151 [Substances - Toxic (Non-combustible)]: Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Cover with plastic sheet to prevent spreading. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. (ERG, 2016)
Excerpt from ERG Guide 151 [Substances - Toxic (Non-combustible)]: 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. (ERG, 2016)|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/
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/
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.
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.
/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.
No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.
Non-irritating to skin and eyes.|Bendiocarb is highly toxic if it is ingested or if it is absorbed through the skin. Absorption through the skin is the most likely route of exposure. Individuals exposed under conditions of high temperature and humidity are at the greatest risk because these conditions promote rapid absorption of bendiocarb across the skin... Irritation and pain, blurred vision, tearing, muscle spasms and unresponsive pupils (to changes in light) may all occur if bendiocarb gets in the eye(s). These effects are due to anti-cholinesterase activity.
U278; A toxic waste when a discarded commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or manufacturing chemical intermediate.
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).
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).
URBAN/SUBURBAN: Bendiocarb was not detected in outdoor air samples tested during summer, spring (1987), or winter (1988) in Jacksonville, FL (estimated 290,000 people residing in 150,000 households), nor in spring or fall (1987) samples in Springfield/Chicopee, MA (estimated 135,000 people residing in 73,000 households). Sampling was conducted over 24 hours and analysis was by GCMS(1). In a study of nine households in urban/suburban southeastern United States during August 1985, bendiocarb was detected outdoors in one household; the detection limit for the GC analysis was 10 ng/cu m(2).|INDOOR: Following aerosol-type spray or compressed-air sprayer application of bendiocarb to indoor rooms, concentrations 0, 1, and 2 days following application were 7.7 ug/cu m, 1.3 ug/cu m, and below detection (detection limit not stated)(1). Bendiocarb (1% in water) was sprayed in a furnished office. Airborne bendiocarb concentrations peaked during application at 2.7 ug/cu m. After 2 hours the level decreased to 0.7 ug/cu m; measurements after 1 and 2 days showed levels of 0.17 and 0.14 ug/cu m, respectively. Bendiocarb deposition during this field experiment ranged from 2.1 to 3.1 ng/sq cm for aluminum plates to 11-25 ng/sq cm for surface wipes of furniture and foil placed on the floor(4). Bendiocarb residues were not detected in indoor air samples during a 9-home pilot monitoring study conducted in 1990 in the Raleigh-Durham-Chapel Hill area, NC(2). Estimated mean air concentrations of bendiocarb were determined for Jacksonville, Florida residents (estimated 290,000 people residing in 150,000 households) as determined by sampling over 24 hours and analysis by GCMS. Indoor air concentrations ranged from 85.7 ng/cu m in the summer to 5.5 ng/cu m in the spring, 1987, to 3.4 ng/cu m in the winter, 1988(5); 23, 20, and 20% of indoor air samples collected in the summer, spring, and winter (from 1986 to 1988), respectively, contained bendiocarb(3). Estimated mean air concentrations of bendiocarb were also determined for Springfield/Chicopee, Massachusetts residents (estimated 135,000 people residing in 73,000 households). Indoor air concentrations were measured as 0.2 ng/cu m in the spring, 1987 and 0 ng/cu m in the winter, 1988(5); 2 and 1% of indoor air samples collected in the spring and winter, respectively, contained bendiocarb(3). In a study of nine households in urban/suburban southeastern United States during August 1985, bendiocarb was detected indoors in 3 households; the detection limit for the GC analysis was 10 ng/cu m(6). Bendiocarb was applied as a 0.5% wettable powder (suspension) to 49 rooms in a North Carolina State University dormitory; indoor air samples were taken for four hours and analyzed using HPLC-UV detection with a detection limit of 0.1 ug. Bendiocarb was detected at 7.7 ug/cu m on day 0, 1.3 ug/cu m on day 1, and was not detected on either day 2 or 3 of this study(7). A bendiocarb concentration of <0.2 ng/cu m was reported in indoor air samples from selected residences in northern Manhattan or South Bronx, New York City, NY; sampling was conducted from 2001-2004(8).|SOURCE DOMINATED: Ambient air collected from the storage and office rooms of 10 North Carolina commercial pest control firms during February 1993 did not contain measurable concentrations of bendiocarb (<0.1 ug/cu m); bendiocarb was stored in 9 of the 10 facilities(1).
Bendiocarb was detected in 4 vacuum cleaner bags containing house dust collected in November 1996 by a residential cleaning service in the Raleigh-Durham-Chapel Hill area, NC(1). Concentrations of 1.43, 0.71, 0.16, 0.18, 0.14, 0.13, and 0.11 ug/g were reported for the following size fractions: <4 um, 4-25, 25-53, 53-106, 106-150, 150-250, and 250-500 um, respectively(1).|Bendiocarb was applied at a rate of 5.9 lb ai/A to azaleas in a greenhouse and the dislodgeable residue on the leaf surfaces measured over 35 days. Analysis was by HPLC-UV detection with a detection limit of 1.8 ug/sq cm leaf area. Dislodgeable bendiocarb residues on the azalea leaves ranged from 10.9 ug/sq cm on day 0 to 4.5 ug/sq cm on day 35. The highest level found was 12.3 ug/sq cm on day 2. The half-life of bendiocarb on azalea leaves was 18.3 days(1).|Bendiocarb was tested for but not detected in fifteen animal feed concentrate samples from Karnal (Haryana) India, post 2000(1).
Toxicity
most toxic
A 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.
LD50 Rat oral 40 mg/kg|LD50 Rat (male) oral 143-179 mg/kg /80% ai water dispersable powder/|LD50 Rat (male) oral 40-156 mg/kg /Unformulated compound/|LD50 Rat dermal 566 mg/kg|For more Non-Human Toxicity Values (Complete) data for BENDIOCARB (11 total), please visit the HSDB record page.
/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.
Persons with asthma, diabetes, cardiovascular disease, mechanical obstruction of the gastrointestinal or ureogenital tract, and those in vagotonic states are at special risk from any route of exposure
Bendiocarb's production may result in its release to the environment through various waste streams; its former use in the USA as an insecticide(1) resulted in its direct release to the environment(SRC). Bendiocarb had turfgrass applications(2). All pesticide products containing bendiocarb were cancelled and no longer allowed to be used in the U.S. as of December 31, 2001(3).
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).
The rate constant for the vapor-phase reaction of bendiocarb with photochemically-produced hydroxyl radicals has been estimated as 2.4X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 16 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). In aqueous alkaline solution, bendiocarb is hydrolyzed to the corresponding phenol. In acidic media, bendiocarb is hydrolyzed to the corresponding phenol; further degradation yields acetone. 50% decomposition occurs in 48 days at pH 5, in 4 days at pH 7, and in 45 minutes at pH 9 at 25 °C(2). The products of neutral hydrolysis are 2,3-isopropylidenedioxyphenol, methylamine and carbon dioxide(3). Photodegradation of bendiocarb in aqueous solution may result in the formation of the corresponding phenol(4). Photolysis half-lives on soil(<30 °C) and in water (25 °C) are 0.33 and 37 days, respectively(5).
An estimated BCF of 6 was calculated in fish for bendiocarb(SRC), using a log Kow of 1.70(1) and a regression-derived equation(2). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
562.34 L/kg|Koc values of 28 to 40 were reported for bendiocarb and its hydrolysis product 2,2-dimethyl-1,3-benzodioxol-4-ol(1); Koc values of 200(2) and 575(3) have also been reported in soil. According to a classification scheme(4), this range of Koc values suggest that bendiocarb is expected to have moderate to very high mobility in soil. While laboratory studies show a high degree of mobility, field studies indicate that parent bendiocarb generally degrades before leaching through the soil(5).
The Henry's Law constant for bendiocarb is estimated as 3.9X10-8 atm-cu m/mole(SRC) derived from its vapor pressure, 3.45X10-5 mm Hg(1), and water solubility, 260 mg/L(1). This Henry's Law constant indicates that bendiocarb is expected to be essentially nonvolatile from water surfaces and moist soil surfaces(2). Bendiocarb is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1). A study was performed to measure bendiocarb volatilization rates from turf plots of Hadley silt loam, that had been planted with creeping bentgrass. The results of the study indicate that from 2-6% of the applied bendiocard active ingredient volatilized from the soil over a 3- to 7-day period of time(3).
GROUNDWATER: Bendiocarb was not detected in groundwater in California during 1985 (4 wells sampled total, 0 detections)(1). Bendiocarb was not detected in groundwater samples collected from 35 golf courses throughout the US and one in Prince Edward Island, Canada; the studies were compiled in 1996(2).|SURFACE WATER: Bendiocarb was not detected in surface water samples collected from 35 golf courses throughout the US and one in Prince Edward Island, Canada; the studies were compiled in 1996(1).
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).
NIOSH (NOES Survey 1981-1983) has statistically estimated that 22,364 workers (907 of these were female) were potentially exposed to bendiocarb in the US(1). The NOES Survey does not include farm workers. Occupational exposure to bendiocarb may occur through inhalation and dermal contact with this compound at workplaces where bendiocarb is produced or used. Monitoring data indicate that the general population may have been exposed to bendiocarb via inhalation of ambient air(SRC). Former use in turfgrass management suggests that the general public may have been exposed to bendiocarb via inhalation of local air on golf courses and dermal contact(SRC).
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).
Drug Information
Pesticides 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. (See all compounds classified as Insecticides.)
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.
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.
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.|Bendiocarb acts through inhibition of cholinesterase activity which is rapidly reversible, the half-life of the inhibited enzyme is approximately 30 minutes.
Excerpt from ERG Guide 151 [Substances - Toxic (Non-combustible)]: Highly toxic, may be fatal if inhaled, swallowed or absorbed through skin. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. (ERG, 2016)
Excerpt from ERG Guide 151 [Substances - Toxic (Non-combustible)]: Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. For minor skin contact, avoid spreading material on unaffected skin. Keep victim calm and warm. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. (ERG, 2016)
Airway protection. Ensure that a clear airway exists. Intubate the patient and aspirate the secretions with a large-bore suction device if necessary. Administer oxygen by mechanically assisted pulmonary ventilation if respiration is depressed. Improve tissue oxygenation as much as possible before administering atropine, to minimize the risk of ventricular fibrillation. In severe poisonings, it may be necessary to support pulmonary ventilation mechanically for several days. /N-methyl carbamate insecticides/|Atropine. Administer atropine sulfate intravenously, or intramuscularly if intravenous injection is not possible. Remember that atropine can be administered through an endotracheal tube if initial IV access is difficult to obtain. Carbamates usually reverse with much smaller dosages of atropine that those required to reverse organophosphates. The objective of atropine antidotal therapy is to antagonize the effects of excessive concentrations of acetylcholine at end-organs having muscarinic receptors. Atropine does not reactivate the cholinesterase enzyme or accelerate excretion or breakdown of carbamate. Recrudescence of poisoning may occur if tissue concentrations of toxicant remain high when the effect of atropine wears off. Atropine is effective against muscarinic manifestations, but is ineffective against nicotinic actions, specifically, muscle weakness and twitching and respiratory depression. Despite these limitations, atropine is often a life-saving agent in N-methyl carbamate poisonings. Favorable response to a test dose of atropine ... given intravenously can help differentiate poisoning by anticholinesterase agents from other conditions such as cardiogenic pulmonary edema and hydrocarbon ingestion. However, lack of response to the test dose, indicating no atropinization (atropine refractoriness), is characteristic of moderately severe to severe poisoning and indicates a need for further atropine. If the test dose does not result in mydriasis and drying of secretions, the patient can be considered atropine refractory. /N-methyl carbamate insecticides/|Skin decontamination. In patients with contaminated skin, clothing, hair, and/or eyes, decontamination must proceed concurrently with what ever resuscitative and antidotal measures are needed to preserve life. Flush the chemical from eyes with copious amounts of clean water. For asymptomatic individuals who are alert and physically able, a prompt shower and shampoo may be appropriate for thorough skin decontamination, provided the patient is carefully observed to insure against sudden appearance of poisoning. If there are any indications of weakness ataxia or other neurologic impairment, clothing should be removed and a complete bath and shampoo given while the victim is recumbent, using copious amounts of soap and water. Attendants should wear rubber gloves as vinyl provides no protection against skin absorption. Wash the chemical from skin folds and from under fingernails. Contaminated clothing should be promptly removed, bagged, and laundered before returning. Contaminated leather shoes should be discarded. Note that the pesticide can contaminate the inside surfaces of gloves, boot, and headgear. /N-methyl carbamate insecticides/|Gastrointestinal decontamination. If N-methyl carbamate has been ingested in a quantity probably sufficient to cause poisoning, consideration should be given to gastrointestinal decontamination ... . If the patient has presented with a recent ingestion and is still asymptomatic, adsorption of poison with activated charcoal may be beneficial. In significant ingestions, diarrhea, and/or vomiting are so constant that charcoal adsorption and catharsis are not indicated. Attention should be given to oxygen, airway management, and atropine. /N-methyl carbamate insecticides/|For more Antidote and Emergency Treatment (Complete) data for BENDIOCARB (20 total), please visit the HSDB record page.
/HUMAN EXPOSURE STUDIES/ In a series of experiments involving oral administration of one to three oral doses of a 76% wettable powder formulation of bendiocarb to human subjects, dose levels ranged from 0.003 to 0.200 mg active ingredient/kg. The threshold dose for mild cholinergic symptoms was between 0.15 and 0.20 mg/kg; the latter dosage was rapidly followed by mild vertigo, nausea, and sweating, with up to 40% inhibition of blood acetylcholinesterase activity. Recovery from these effects was notable 30 min after dosing and complete within 4 hr.|/HUMAN EXPOSURE STUDIES/ ... Repeated ingestion of 0.1 mg ai/kg at hourly intervals was without symptoms.|/HUMAN EXPOSURE STUDIES/ A double-blind cross over experiment involving three ... male volunteers indicated a single dose of 0.004 mg/kg body weight, the only dose administered, of the 80% w.p. resulting in no adverse effects on any of the parameters assessed (heart rate, clinical signs, mean diastolic/systolic pressure and whole blood cholinesterase). Following a single dose of 0.12 mg/kg body weight of the 80% w.p. given orally to the same three volunteers 72 hours later in another similar experiment, a transient depression (21% of whole blood cholinesterase was observed in one of the three subjects at 30 minutes post-treatment.|/HUMAN EXPOSURE STUDIES/ In a 60-year old male volunteer given bendiocarb (as an 80% wettable powder) orally in H2O serially at 0.004, 0.012, 0.037, 0.125, 0.187 and 0.25 mg/kg body weight (dosage in terms of w.p.) with at least a 48-hour interval between doses, 0.125 mg/kg was found to be a clear-cut no-effect level on symptoms and whole blood cholinesterase. Toxic sumptoms such as mild vertigo, nausea and vomiting together with significant inhibition (30-40%) of whole blood cholinesterase were induced after the single dose at 0.25 mg/kg body weight. The symptoms subsided in 30 minutes and whole blood cholinesterase recovered completely in 4 hours post-treatment. In the same subject, doses of the 80% w.p. at 0.125 mg/kg given orally at an interval of 4 hours, but not less, produced no toxic signs or inhibition of whole blood cholinesterase.|For more Human Toxicity Excerpts (Complete) data for BENDIOCARB (12 total), please visit the HSDB record page.
bendiocarb
Bendiocarb Use and Manufacturing
Produced by the reaction of 2,3-isopropylidenedioxyphenol with methyl isocyanate ... .
Contact insecticide.
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
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.
Method: USGS-NWQL O-2060-01; Procedure: high performance liquid chromatography-mass spectrometry; Analyte: bendiocarb; Matrix: water; Detection Limit: 0.0126 ug/L.|Product analysis by HPLC...Residue analysis of foodstuffs by GLC.|Field desorption for mass spectra analysis for carbamate and urea pesticides, incl bendiocarb.|OSW Method 8321A. Determination of Solvent Extractable Non-Volatile Compounds by High Performance Liquid Chromatography/ Thermospray/Mass Spectrometry (HPLC/TSP/MS) or Ultraviolet (UV) Detection.|For more Analytic Laboratory Methods (Complete) data for BENDIOCARB (8 total), please visit the HSDB record page.
A mass fragmentographic method for the determination of the bendiocarb metabolite 2,2-dimethylbenzo-1,3-dioxol-4-ol in human urine was developed. The method can be used to est the amt absorbed by persons during mfg or spraying, by collection of urine for 16 hr after the period of exposure. Determination is possible at levels of 1 ug bendiocarb/ml. The method can determine the absorption of 1 mg of bendiocarb and will detect absorption below that.
Agrochemicals -> Insecticides
Computed Properties
Molecular Weight:223.22
XLogP3:1.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:223.08445790
Monoisotopic Mass:223.08445790
Topological Polar Surface Area:56.8
Heavy Atom Count:16
Complexity:279
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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