Naled CAS 300-76-5
Introduction：Basic information about Naled CAS 300-76-5, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Naled Basic information
| Product Name: | Naled |
| Synonyms: | DIBROM;DIBROM (NALED);BROMEX;BROMCHLOPHOS;BRP;1,2-DIBROMO-2,2-DICHLOROETHYL DIMETHYL-PHOSPHATE;RE-4355;O,O'-DIMETHYL-1,2-DIBROMO-2,2-DICHLOROETHYL PHOSPHATE |
| CAS: | 300-76-5 |
| MF: | C4H7Br2Cl2O4P |
| MW: | 380.78 |
| EINECS: | 206-098-3 |
| Product Categories: | Aliphatics;Phosphorylating and Phosphitylating Agents |
| Mol File: | 300-76-5.mol |
Naled Chemical Properties
| Melting point | 212℃ (decomposition) |
| Boiling point | 110℃ (0.5 Torr) |
| density | 1.96 g/cm3 |
| vapor pressure | 2 (quoted, Verschueren, 1983) |
| refractive index | 1.5108 (28℃) |
| storage temp. | 0-6°C |
| solubility | Freely soluble in ketone, alcohols, aromatic and chlorinated hydrocarbons but sparingly soluble inpetroleum solvents and mineral oils (Windholz et al., 1983) |
| Water Solubility | 2000mg l-1(20 °C) |
| form | solid |
| Specific Gravity | 1.96 (20℃) |
| Merck | 13,6384 |
| BRN | 2049930 |
| Exposure limits | NIOSH REL: TWA 3 mg/m3, IDLH 200 mg/m3; OSHA PEL: TWA 3mg/m3; ACGIH TLV: TWA 3 mg/m3. |
| Stability: | Light Sensitive, Moisture Sensitive |
| Major Application | agriculture environmental |
| InChI | 1S/C4H7Br2Cl2O4P/c1-10-13(9,11-2)12-3(5)4(6,7)8/h3H,1-2H3 |
| InChIKey | BUYMVQAILCEWRR-UHFFFAOYSA-N |
| SMILES | COP(=O)(OC)OC(Br)C(Cl)(Cl)Br |
| EPA Substance Registry System | Naled (300-76-5) |
Safety Information
| Hazard Codes | Xn,N,T |
| Risk Statements | 21/22-36/38-50-25-21 |
| Safety Statements | 36/37-61-26 |
| OEB | B |
| OEL | TWA: 3 mg/m3 [skin] |
| RIDADR | 3018 |
| WGK Germany | 3 |
| RTECS | TB9450000 |
| HazardClass | 6.1(a) |
| PackingGroup | I |
| HS Code | 29199000 |
| Storage Class | 6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects |
| Hazard Classifications | Acute Tox. 3 Oral Acute Tox. 4 Dermal Aquatic Acute 1 Eye Irrit. 2 Skin Irrit. 2 |
| Hazardous Substances Data | 300-76-5(Hazardous Substances Data) |
| Toxicity | LD50 in male rats (mg/kg): 250 orally; 800 dermally (Gaines) |
| IDLA | 200 mg/m3 |
| Description | Sensitization to Naled seems to be rare. |
| Description | Naled is an organophosphate insecticide and acaricide that inhibits acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). It reduces the number of A. sollicitans mosquitos by 97% after one hour when aerially applied at a concentration of 0.1 pounds per acre. Naled (125 ppm AI) induces 100 and 64% mortality of T. telarius adults and immature mites, respectively, in an immediate contact toxicity test but does not induce mortality in mite eggs. It is toxic to rats with an LD50 value of 250 mg/kg. Formulations containing naled have been used in the control of mosquitoes in public areas and of crop-damaging insects in agriculture. |
| Chemical Properties | Clear Colorless Liquid |
| Chemical Properties | Naled is a white crystalline solid (when pure)or light straw-colored liquid (above 26.7℃) with a slightlypungent insecticide odor. |
| Physical properties | Colorless to pale yellow liquid or solid with a pungent odor |
| Uses | Naled is used to control mites, sucking pests and some otherinsects in a wide variety of crops. It is also used for the control of publicand animal health pests including mosquitoes. |
| Uses | Insecticide used for control of spider mites, sucking and chewing insects in fruits,vegetables and ornamentals. Its use may be restricted. |
| Uses | A cholinesterase inhibitor. Insecticide; acaricide. |
| Uses | Insecticide; acaricide. |
| Definition | ChEBI: An dialkyl phosphate resulting from the formal condensation of the acidic hydroxy group of dimethyl hydrogen phosphate with the alcoholic hydroxy group of 1,2-dibromo-2,2-dichloroethanol. An organophosphate insecticide, it is no longer approved for use witin the European Union. |
| General Description | DIBROM is a white solid that may be dissolved in a liquid organic carrier with a pungent odor. DIBROM is a water emulsifiable liquid. DIBROM is insoluble in water and sinks in water. DIBROM can cause illness by inhalation, skin absorption and/or ingestion. The primary hazard is the threat to the environment. Immediate steps should be taken to limit its spread to the environment. If DIBROM is in liquid form, DIBROM can easily penetrate the soil and contaminate groundwater and nearby streams. DIBROM is used as a pesticide. |
| 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 solublein 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) |
| Agricultural Uses | Insecticide, Fungicide, Bactericide, Acaricide: Naled is a fast-acting, nonsystemic contact and stomachinsecticide used to control aphids, mites, mosquitoes,and flies on crops and in greenhouses, mushroom houses,animal and poultry houses, kennels, food-processingplants, and aquaria and in outdoor mosquito control. Liquidformulations can be applied to greenhouse heating pipes tokill insects by vapor action. It has been used by veterinariansto kill parasitic worms (other than tapeworms) in dogs.Naled may no longer be used in and around the home byresidents or professional applicators. Naled is available indust, emulsion concentrate, liquid, and ULV formulations.Also used in cooling towers, veterinary medicine, pulp andpaper mill systems, hospitals, swimming pools, and bathrooms.A U.S. EPA restricted Use Pesticide (RUP). Notapproved for use in EU countries. Registered for use inthe U.S. |
| 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 inhibitorthat is used as an insecticide and acaricide. Sensitizationseems to be very rare. |
| Potential Exposure | A potential danger to those involvedin the manufacture, formulation, and application of thisinsecticide, fungicide, bactericide, acaricide. Also used incooling towers, veterinary medicine, pulp and paper millsystems; 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 inmineralization of spinal cord, and mild testicular degenerationin males occurred at 2 and 20 mg/kg/day doselevels . Erythrocyte and brain cholinesterase activitieswere depressed at the same dose levels. Anemia alsooccurred 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 butthese 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 heatedto decomposition (Lewis, 1990). |
| Metabolic pathway | Naled is produced by the photochemical bromination of the dichlorovinylmoiety of dichlorvos. The main route of naled metabolism and transformationin the environment is through debromination to dichlorvoswhich is probably the active cholinesterase inhibitor in vivo. Naled is alsorapidly hydrolysed to bromodichloroacetaldehyde in aqueous environments:consequently much of its detoxification is likely to be via a nonenzymatichydrolytic route. |
| Solubility in water | Freely soluble in ketone, alcohols, aromatic and chlorinated hydrocarbons but sparingly soluble inpetroleum solvents and mineral oils (Windholz et al., 1983) |
| Shipping | UN2811 Toxic solids, organic, n.o.s., HazardClass: 6.1; Labels: 6.1-Poisonous materials, TechnicalName 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 mediaand 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 rapidlyhydrolysed via two routes, one leading to the formation of dimethylphosphate (3) and bromodichloroacetaldehyde (4) and the second viadesmethyhaled (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 dichlorvosand 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 ofwater. Degraded by sunlight. Decomposes when heated; oncontact with acids, acid fumes; bases, producing fumes ofhydrogen chloride, hydrogen bromide, phosphorous oxides.Reacts with acids, strong oxidizers in sunlight. Slowlyreacts with water; hydrolysis is; corrosive to metals.Attacks some plastics, rubber and coatings. |
| Waste Disposal | This pesticide is morestable to hydrolysis than dichlorvos (50% hydrolysis at pH9 @ 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 ambientwater. Incineration is recommended for large amounts.In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers. Mustbe disposed properly by following package label directionsor by contacting your local or federal environmental controlagency, or by contacting your regional EPA office. |
| References | [1] P. HERZSPRUNG R N L Weil. Measurement of Bimolecular Rate Constants k i of the Cholinesterase Inactivation Reaction by 55 Insecticides and of the Influence of Various Pyridiniumoximes on k i[J]. International Journal of Environmental Analytical Chemistry, 1992, 47 1: 181-200. DOI: 10.1080/03067319208027028 [2] MITCHELL H R. Part I: Comparison of an “As-Needed” and “Full-Season” Insecticide Application Schedule for Control of Cotton Insects in Northeast Louisiana. Part II: the Utilization of Vegetable Oil as a Carrier for Ultra-Low-Volume Aerial Sprays Applied for Cotton Insect Control.[C]. 1900: 0. DOI: 10.31390/gradschool_disstheses.4064 [3] M. MATLLOUX F O M. The Effects of Acaricides on the Developmental Stages of the Two-Spotted Spider Mite, Tetranychu telarius[J]. Journal of Economic Entomology, 1962, 55 1: 479-483. DOI: 10.1093/jee/55.4.479 [4] GAINES T B. Acute toxicity of pesticides[J]. Toxicology and applied pharmacology, 1969, 14 3: Pages 515-534. DOI: 10.1016/0041-008x(69)90013-1 |
Naled Preparation Products And Raw materials
| Raw materials | Benzoyl peroxide-->Dichlorvos |
