300-76-5 Usage
Description
DIBROM, also known as Naled, is an organophosphate insecticide and acaricide that inhibits acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). It is a white solid that may be dissolved in a liquid organic carrier with a pungent odor. DIBROM is a water emulsifiable liquid, insoluble in water, and can cause illness by inhalation, skin absorption, and/or ingestion. The primary hazard is the threat to the environment, and immediate steps should be taken to limit its spread.
Uses
Used in Agricultural Industry:
DIBROM is used as an insecticide, fungicide, bactericide, and acaricide for controlling aphids, mites, mosquitoes, and flies on crops and in greenhouses, mushroom houses, animal and poultry houses, kennels, food-processing plants, and aquaria. It is a fast-acting, nonsystemic contact and stomach insecticide. Liquid formulations can be applied to greenhouse heating pipes to kill insects by vapor action. It has been used by veterinarians to kill parasitic worms (other than tapeworms) in dogs.
Used in Public and Animal Health:
DIBROM is used to control mites, sucking pests, and some other insects in a wide variety of crops. It is also used for the control of public and animal health pests, including mosquitoes.
Used in Veterinary Medicine:
DIBROM is used in veterinary medicine to kill parasitic worms (other than tapeworms) in dogs.
Used in Other Industries:
DIBROM is also used in cooling towers, pulp and paper mill systems, hospitals, swimming pools, and bathrooms.
Note: DIBROM may have its use restricted or may no longer be used in and around the home by residents or professional applicators. It is a U.S. EPA restricted Use Pesticide (RUP), not approved for use in EU countries, and registered for use in the U.S.
Air & Water Reactions
Practically insoluble in water [Farm Chemicals Handbook]. Hydrolyzed slowly in presence of water.
Reactivity Profile
DIBROM is incompatible with the following: Strong oxidizers, acids, sunlight, water [Note: Corrosive to metals. Hydrolyzed in presence of water.] . Unstable in presence of Iron [USCG, 1999]. Organophosphates are susceptible to formation of highly toxic and flammable phosphine gas in the presence of strong reducing agents such as hydrides. Partial oxidation by oxidizing agents may result in the release of toxic phosphorus oxides.
Hazard
Technical compound is a moderately volatile liquid. Bp 110C (0.5 mm Hg). Insoluble in water;
slightly soluble in aliphatic solvents; very soluble
in aromatic solvents; hydrolyzes in water.
Health Hazard
INHALATION OR INGESTION: Symptoms secondary to cholinesterase inhibition are: headache, giddiness, nervousness, blurred vision, weakness, nausea, cramps, diarrhea, chest discomfort, sweating, miosis, tearing, salivation, and other excessive respiratory tract secretion, vomiting, cyanosis, muscle twitching, and convulsions. EYES: Irritating. SKIN: Irritating-can cause dermatitis.
Fire Hazard
May be combustible. (NOAA, 2007)
Trade name
AI3-24988?; ARTHODIBROM?;
BROMCHLOPHOS?; BROMEX?; DIBROM?;
FLYKILLER?; LUCANAL?; HIBROM?; ORTHO?
4355; ORTHODIBROM?; ORTHODIBROMO?;
PROKIL? Naled; TRUMPET?
Contact allergens
Naled is an organophosphate cholinesterase inhibitor
that is used as an insecticide and acaricide. Sensitization
seems to be very rare.
Potential Exposure
A potential danger to those involved
in the manufacture, formulation, and application of this
insecticide, fungicide, bactericide, acaricide. Also used in
cooling towers, veterinary medicine, pulp and paper mill
systems; hospitals, swimming pools; and bathrooms.
Carcinogenicity
When dogs were given 0.2, 2.0,
or 20 mg/kg/day naled by gavage for 1 year, cholinergic signs
(soft stools/diarrhea, salivation, and emesis), increases in
mineralization of spinal cord, and mild testicular degeneration
in males occurred at 2 and 20 mg/kg/day dose
levels . Erythrocyte and brain cholinesterase activities
were depressed at the same dose levels. Anemia also
occurred at 2 and 20 mg/kg/day, and erythrocyte count,
hemoglobin, and hematocrit were reduced. At 20 mg/kg/
day dose level, liver and kidney weights increased but
these were not accompanied by histopathological changes.
There was no evidence of carcinogenicity.
Environmental Fate
Chemical/Physical. Completely hydrolyzed in water within 2 days (Windholz et al.,
1983). In the presence of metals or reducing agents, naled loses bromine, forming dichlorvos
(Hartley and Kidd, 1987)Naled emits toxic fumes of bromines, chlorides and phosphorus oxides when heated
to decomposition (Lewis, 1990).
Metabolic pathway
Naled is produced by the photochemical bromination of the dichlorovinyl
moiety of dichlorvos. The main route of naled metabolism and transformation
in the environment is through debromination to dichlorvos
which is probably the active cholinesterase inhibitor in vivo. Naled is also
rapidly hydrolysed to bromodichloroacetaldehyde in aqueous environments:
consequently much of its detoxification is likely to be via a nonenzymatic
hydrolytic route.
Solubility in water
Freely soluble in ketone, alcohols, aromatic and chlorinated hydrocarbons but sparingly soluble in
petroleum solvents and mineral oils (Windholz et al., 1983)
Shipping
UN2811 Toxic solids, organic, n.o.s., Hazard
Class: 6.1; Labels: 6.1-Poisonous materials, Technical
Name Required. UN2783 Organophosphorus pesticides,
solid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.
UN3018 Organophosphorus pesticides, liquid, toxic,
Hazard Class: 6.1; Labels: 6.1-Poisonous materials.
Degradation
Naled is stable when dry but it is rapidly hydrolysed in aqueous media
and more rapidly in alkaline and acidic media. It is degraded by sunlight.
In the presence of metals and reducing agents, bromine is lost and dichlorvos
(2) is formed (PM). In unbuffered aqueous solution naled was rapidly
hydrolysed via two routes, one leading to the formation of dimethyl
phosphate (3) and bromodichloroacetaldehyde (4) and the second via
desmethyhaled (5), which further decomposed to yield bromodichloroacetaldehyde
(4) and monomethyl phosphate (6) as shown in Scheme 1.
Naled was found to be much less hydrolytically stable than dichlorvos
and exhibited a maximum stability at pH 4 (Jentzen and Fischer, 1978).
Incompatibilities
Incompatible with oxidizers (chlorates,
nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions.
Keep away from alkaline materials, strong bases,
strong acids, oxoacids, epoxides. Hydrolyzed in presence of
water. Degraded by sunlight. Decomposes when heated; on
contact with acids, acid fumes; bases, producing fumes of
hydrogen chloride, hydrogen bromide, phosphorous oxides.
Reacts with acids, strong oxidizers in sunlight. Slowly
reacts with water; hydrolysis is; corrosive to metals.
Attacks some plastics, rubber and coatings.
Waste Disposal
This pesticide is more
stable to hydrolysis than dichlorvos (50% hydrolysis at pH
9 @ 37.5℃ in 301 minutes). It is unstable in alkaline conditions,
in presence of iron; and is degraded by sunlight.
About 10% hydrolysis per day is obtained in ambient
water. Incineration is recommended for large amounts.
In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers. 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.
Check Digit Verification of cas no
The CAS Registry Mumber 300-76-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 3,0 and 0 respectively; the second part has 2 digits, 7 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 300-76:
(5*3)+(4*0)+(3*0)+(2*7)+(1*6)=35
35 % 10 = 5
So 300-76-5 is a valid CAS Registry Number.
InChI:InChI=1/C4H7Br2Cl2O4P/c1-10-13(9,11-2)12-3(5)4(6,7)8/h3H,1-2H3
300-76-5Relevant articles and documents
Process for preparing peroxides
-
, (2008/06/13)
A process for the faster manufacturing of hydrocarbon, fluorocarbon and chlorocarbon acyl peroxides is disclosed wherein a hydroxide, a peroxide and an acyl halide are reacted under continuous vigorous agitation conditions so as to bring the reaction to substantial completion is less than one minute.
Pesticide compositions
-
, (2008/06/13)
Toxicant, especially pesticide compositions, having lowered dermal toxicity are provided. The compositions include a microencapsulated lipophilicpesticide, a hydrophilic surfactant and water. Methods for reducing the dermal toxicity of microencapsulated lipophilic toxicants, especially pesticides are provided. Methods for controlling insect pests using the disclosed compositions are provided.
Propynyl benzyl ethers
-
, (2008/06/13)
Propynyl benzyl ethers having juvenile hormone-like activity which are 4-halogen, lower alkyl, lower alkoxy or propynyloxy substituted or 3,4-lower alkylenedioxy substituted and which can also be 3,5- and/or α-substituted, and insecticide compositions that include at least one propynyl benzyl ether and that can also include a conventional insect-poison.
