| Identification | More | [Name]
BENDIOCARB | [CAS]
22781-23-3 | [Synonyms]
2,2-DIMETHYLBENZO-1,3-DIOXOL-4-YL METHYL-CARBAMATE
2,3-ISOPROPYLIDENDIOXYPHENYL N-METHYLCARBAMATE
2，3-Isopropylidenedioxyphenyl methylcarbamate
BENCARBATE
BENDIOCARB
DYCARB
FICAM
FICAM(R)
GARVOX
MULTAMAT
SEEDOX
1,3-Benzodioxol-4-ol, 2,2-dimethyl-, methylcarbamate
1,3-Benzodioxole, 2,2-dimethyl-4-(N-methylaminocarboxylato)-
1,3-Benzodioxole, 2,2-dimethyl-4-(N-methylcarbamato)-
2,2-Dimethyl-1,3-benzdioxol-4-yl N-methylcarbamate
2,2-dimethyl-1,3-benzdioxol-4-yln-methylcarbamate
2,2-Dimethyl-1,3-benzodioxol-4-ol methylcarbamate
2,2-dimethyl-1,3-benzodioxol-4-olmethylcarbamate
2,2-Dimethyl-1,3-benzodioxol-4-yl methylcarbamate
2,2-dimethyl-1,3-benzodioxol-4-ylmethylcarbamate | [EINECS(EC#)]
245-216-8 | [Molecular Formula]
C11H13NO4 | [MDL Number]
MFCD00078629 | [Molecular Weight]
223.23 | [MOL File]
22781-23-3.mol |
| Chemical Properties | Back Directory | [Description]
Bendiocarb is an odourless, non-corrosive white crystalline solid. Bendiocarb is a carbamate
ester. Carbamates are chemically similar to but more reactive than amides. Like amides, they
form polymers such as polyurethane resins. Some of the formulations of bendiocarb are
classified as general use pesticides (GUP), while Turcam and its 2.5 G formulation have been
classified as restricted use pesticides (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 noncorrosive. Flammable gaseous
hydrogen is produced by the combination of active metals or nitrides with carbamates.
Strongly oxidising acids, peroxides, and hydroperoxides are incompatible with carbamates.
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, flies, wasps, ants,
fleas, cockroaches, silverfish, ticks, and other pests in homes, industrial plants, and food
storage sites. 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 wettable powders. It gets hydrolysed rapidly in alkali
media and slows under acid and neutral conditions. Flammable gaseous hydrogen is produced
by the combination of active metals or nitrides with carbamates. | [Appearance]
Bendiocarb is a white odorless crystalline
powder. | [Melting point ]
129-130° | [Boiling point ]
364.51°C (rough estimate) | [density ]
1.2500 | [vapor pressure ]
4.6 x 10-3 Pa (25 °C) | [refractive index ]
1.4960 (estimate) | [Fp ]
>100 °C | [storage temp. ]
0-6°C | [solubility ]
DMF: 30 mg/ml,DMSO: 30 mg/ml,DMSO:PBS (pH 7.2) (1:9): 0.1 mg/ml,Ethanol: 5 mg/ml | [form ]
Powder/Solid | [pka]
11.98±0.46(Predicted) | [Water Solubility ]
280 mg l-1 (20 °C) | [color ]
White | [Merck ]
13,1033 | [BRN ]
1315404 | [InChIKey]
XEGGRYVFLWGFHI-UHFFFAOYSA-N | [CAS DataBase Reference]
22781-23-3(CAS DataBase Reference) | [NIST Chemistry Reference]
Bendiocarb(22781-23-3) | [EPA Substance Registry System]
22781-23-3(EPA Substance) |
| Hazard Information | Back Directory | [Chemical Properties]
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 | [General Description]
White solid. Melting point 265°F (129-30°C). Insoluble in water. Used as a contact insecticide. | [Reactivity Profile]
BENDIOCARB(22781-23-3) 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. | [Air & Water Reactions]
Insoluble in water. | [Hazard]
Poison by ingestion, skin absorption. | [Health Hazard]
Bendiocarb is moderately toxic if ingested or absorbed through the skin. Absorption
through the skin is the most likely route of exposure. Bendiocarb is absorbed through
all the normal routes (oral, dermal, and inhalation) of exposure, but dermal absorption
is especially rapid. Carbamates are generally excreted rapidly and do not accumulate
in mammalian tissue. If exposure does not continue, cholinesterase inhibition and its
symptoms reverse rapidly. In non-fatal cases, the illness generally lasts less than 24 h.
Bendiocarb is moderately toxic to birds. The LD50 in mallard ducks and quail is 3.1 and
19 mg/kg, respectively. Bendiocarb is moderately to highly toxic to i sh. The LC50 (96 h) for
bendiocarb in rainbow trout is 1.55 mg/L.
Bendiocarb is a mild irritant to the skin and eyes. Symptoms of bendiocarb poisoning
include, but are not limited to, weakness, blurred vision, headache, nausea, abdominal
cramps, chest discomfort, constriction of pupils, sweating, muscle tremors, and decreased
pulse. Prolonged exposures to high concentrations of bendiocarb cause severe poisoning
with symptoms of twitching, giddiness, confusion, muscle incoordination, slurred speech,
low blood pressure, heart irregularities, and loss of rel exes may also be experienced.
Death can result from respiratory arrest, paralysis of the muscles of the respiratory system,
intense constriction of the openings of the lung, or all three. In one case of exposure while
applying bendiocarb, the victim experienced symptoms of severe headache, vomiting,
and excessive salivation, and his cholinesterase level was depressed by 63%. He recovered
from these symptoms in less than 3 h with no medical treatment and his cholinesterase
level returned to normal within 24 h. In another case, poisoning occurred when an appli-
cator, who was not wearing protective equipment, attempted to clean contaminated equip-
ment. The victim experienced nausea, vomiting, incoordination, pain in his arms, hands,
and legs, muscle spasms, and breathing difi culties. Bendiocarb is readily absorbed by the
gastrointestinal tract and is rapidly metabolized. | [Potential Exposure]
A potential danger to those involved
in the manufacture, formulation and application of this carbamate
insecticide which is used against household pests,
in agriculture in seed treatment, and as a foliar spray. | [First aid]
If this chemical gets into the eyes, remove any
contact lenses at once and irrigate immediately for at least
15 minutes, occasionally lifting upper and lower lids. Seek
medical attention immediately. If this chemical contacts the
skin, remove contaminated clothing and wash immediately
with soap and water. Shampoo hair. Seek medical attention
immediately. If this chemical has been inhaled, remove
from exposure, begin rescue breathing (using universal precautions,
including resuscitation mask) if breathing has
stopped and CPR if heart action has stopped. Transfer
promptly to a medical facility. When this chemical has
been swallowed, get medical attention. Give large quantities
of water and induce vomiting. Do not make an unconscious
person vomit. | [Shipping]
UN2757 Carbamate pesticides, solid, toxic,
Hazard Class: 6.1; Labels: 6.1—Poisonous materials.
UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1;
Labels: 6.1—Poisonous materials, Technical Name
Required. | [Incompatibilities]
Carbamates are incompatible with reducing
agents, strong acids, oxidizing acids, peroxides, and
bases. Contact with active metals or nitrides cause the
360 Bendiocarb
release of flammable, and potentially explosive, hydrogen
gas. May react violently with bromine, ketones.
Incompatible with azo dyes, caustics, ammonia, amines,
boranes, hydrazines, strong oxidizers. Keep away from
flammable materials and sources of heat and flame. | [Waste Disposal]
Must be disposed properly by
following package label directions or by contacting your
local or federal environmental control agency, or by contacting
your regional EPA office. Dispose in accordance
with 40CFR165 recommendations for the disposal of pesticides
and pesticide containers. | [Uses]
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. | [Uses]
Bendiocarb is a contact and ingested insecticide with some systemic
activity in crop plants. It is active against many public health,
industrial and storage pests such as Formicidae, Blattodae, Culicidae,
Muscidae and Siphonaptera. | [Uses]
Contact insecticide used to control beetles, wireworms, flies, wasps and mosquitoes
in beets and maize. | [Uses]
Contact insecticide. | [Definition]
ChEBI: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 is functionally related to a methylcarbamic acid. | [Environmental Fate]
Soil. Though no products were identified, the reported half-life in soil is several days
to a few weeks (Hartley and Kidd, 1987). When soil containing bendiocarb was incubated
for 4 weeks, the amount remaining was 30.4–47.2% of the applied amount. After one
application, the amount of bendiocarb recovered was only 0.9–1.3% (Racke and Coates,
1988). Biodegradation of bendiocarb in soil was enhanced if the soil was pretreated with
carbofuran or trimethacarb (Dzantor and Felsot, 1989).
Plant. At planting, bendiocarb was applied at a rate of 1.7 kg/ha. During harvest (110
days following planting), the residues of bendiocarb found in corn (leaves and stems),
husks, cobs and kernels were 12, 5, 4 and 3 ppb, respectively. At an app
Chemical/Physical. Bendiocarb is stable to light but in water hydrolyzes to 2,3-
isopropylidenedioxyphenol, methylamine and carbon dioxide. The hydrolysis half-life at
pH 7 and 25°C is 4 days (Worthing and Hance, 1991). | [Metabolic pathway]
Pathways of bendiocarb metabolism in mammals include hydrolysis to
the benzodioxol-4-ol, hydroxylation of the phenyl ring, hydroxylation at
the N-methyl moiety and conjugation. Extensive pathways reported for
the structurally related carbofuran are not reported for bendiocarb partly
because hydroxylation and subsequent oxidation and conjugation at the
3-position is not possible in bendiocarb although it is a major pathway for
carbofuran. No domation is available for the metabolism of bendiocarb
in plants. | [storage]
Store at Room temperature | [Degradation]
Bendiocarb undergoes base-catalysed hydrolysis but is more stable in
neutral or acidic conditions. The products of hydrolysis are 2,2-dimethyl-
1,3-benzodioxol-4-ol(2), methylamine and CO2. Its DT50 at ph 7 and 25 °C
is 4 days (PM). |
| Safety Data | Back Directory | [Hazard Codes ]
T,N | [Risk Statements ]
R21:Harmful in contact with skin.
R23/25:Toxic by inhalation and if swallowed .
R50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment . | [Safety Statements ]
S22:Do not breathe dust .
S36/37:Wear suitable protective clothing and gloves .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S60:This material and/or its container must be disposed of as hazardous waste .
S61:Avoid release to the environment. Refer to special instructions safety data sheet . | [RIDADR ]
2757 | [WGK Germany ]
3 | [RTECS ]
FC1140000 | [HazardClass ]
6.1(a) | [PackingGroup ]
II | [HS Code ]
29329990 | [Precautions]
The preliminary risk assessment of the US EPA showed that applicators, including home
owners, were at risk when mixing or applying the pesticide. Thus, bendiocarb is no longer
sold in the United States. All bendiocarb-containing products in the United States recently
had their registrations cancelled due to concerns over exposure of those applying the
products. In the UK, however, bendiocarb is still registered as a biocide and amateurs can
use it even though it lacks proper warning labels. In view of this, bendiocarb should be
purchased and used only by certii ed and trained applicators. Like all RUPs, management
must be done only by trained and certii ed workers. | [Safety Profile]
Poison by ingestion.
Moderately toxic by skin contact. When
heated to decomposition it emits toxic
fumes of NOx. See also CARBAMATES.
| [Hazardous Substances Data]
22781-23-3(Hazardous Substances Data) | [Toxicity]
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). |
| Questions And Answer | Back Directory | [Description]
Bendiocarb belongs to a kind of carbamate insecticide. It can be used in homes, industrial plants and food storage sites for the treatment of various kinds of insects including mosquitoes, flies, wasps, ants, fleas, cockroaches, spider, silverfish, ticks and other pests in homes, industrial plants, and food storage sites. In agriculture, it is used for the treatment of a variety of insects such as beetles, aphids, mites and caterpillars. Bendiocarb can block the activity of some enzymes necessary for the normal nerve transmission, further affecting the normal operation of the insects’ nervous system. It can kill the pests through either contact or ingestion. However, its applications have been cancelled in some countries including the United States due to its toxicity effects on Human beings and other animals including birds and fishes. | [References]
https://en.wikipedia.org/wiki/Bendiocarb
http://npic.orst.edu/factsheets/bendiogen.pdf
http://pmep.cce.cornell.edu/profiles/extoxnet/24d-captan/bendiocarb-ext.html
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