Bromophos-ethyl
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Bromophos-ethyl
structure -
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CAS No:
4824-78-6
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Formula:
C10H12BrCl2O3PS
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Chemical Name:
Bromophos-ethyl
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Synonyms:
Phosphorothioic acid,O-(4-bromo-2,5-dichlorophenyl) O,O-diethyl ester;O-(4-Bromo-2,5-dichlorophenyl) O,O-diethyl phosphorothioate;Bromophos-ethyl;Ethyl bromophos;OMS 659;O,O-Diethyl O-(2,5-dichloro-4-bromophenyl) thiophosphate;Nexagan G;Filariol 60;Filariol;Nexagan;Bromophos A;37370-22-2
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CAS No:
Bromophos-ethyl Basic Attributes
394.05
394.05
225-399-0
CVT4KYL79N
DTXSID6041684
Colorless to pale yellow liquid
29201900
Characteristics
59.8
6.15
1.52-1.55 g/cm3 @ Temp: 20 °C
122-133 °C @ Press: 1 x 10-3 Torr
100 °C
1.575
In water, 0.44 mg/l @ 20 deg C
0-6°C
4.6X10-5 mm Hg @ 30 deg C (6.1 mPa at 30 deg C)
Oral-rat LD50: 52 mg/kg; Oral-Mouse LD50: 210 mg/kg
Decomposes toxic phosphorus oxide, sulfur oxide, halide gas by heating
166.45 Ų [M+H]+
Compatible with all pesticides except sulphur and organometallic compounds.
Non-corrosive
Safety Information
II
6.1(a)
3018
3
21-25-50/53
28-36/37-45-60-61
TE7000000
T,N
The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials
Stable in aqueous suspension up to pH 9. Slowly hydrolyzed in aqueous alkaline media above pH 9.
P273-P280-P301 + P310-P501
H301-H312-H410
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Tafuri J, Roberts J; Organophosphate Poisoning; Ann Emerg Med 16 (2): 193-202 (1987)
|Danger|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P264, P270, P273, P280, P301+P310, P302+P352, P312, P321, P322, P330, P363, P391, P405, and P501|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|Aggregated GHS information provided by 41 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
USE OF RUBBER GLOVES, GOGGLES, RESPIRATOR &...PROTECTIVE CLOTHING. /ORGANOPHOSPHORUS PESTICIDES/|WORKERS HANDLING AND APPLYING ORGANOPHOSPHORUS PESTICIDES ... MUST BE GIVEN PERSONAL PROTECTIVE EQUIPMENT COMPRISING OVERALLS MADE OF A TIGHT FABRIC OR POLYVINYL CHLORIDE, GLOVES AND RUBBER BOOTS. THEY MUST WEAR A RESPIRATOR WITH AN ACTIVATED-CARBON GAS FILTER CARTRIDGE AFFORDING PROTECTION FOR A DETERMINED NUMBER OF WORKING HOURS. THE EYES SHOULD BE PROTECTED BY GOGGLES. ... /ORGANOPHOSPHORUS PESTICIDES/
ANY MATERIAL SPILLED ON SKIN SHOULD BE IMMEDIATELY REMOVED WITH SOAP & WATER. WHEN SPRAYING & DUSTING...CONTAMINATED CLOTHING SHOULD BE CHANGED FREQUENTLY. /ORGANOPHOSPHORUS PESTICIDES/|CONTAINERS ... SHOULD BE CLEANED WITH A SUSPENSION OF BLEACHING POWDER IN WATER OR WITH OTHER ALKALINE SOLN AFTER SOAKING FOR 24 HR AND THEN BE RINSED WITH HOT WATER. /ORGANOPHOSPHORUS PESTICIDES/|THE STRICT OBSERVANCE OF HYGIENE RULES- NO SMOKING AND NO FOOD INTAKE DURING WORK, THOROUGH WASHING WITH SOAP AFTER WORK, CHANGING PROTECTIVE CLOTHING BEFORE GOING HOME- IS OF THE UTMOST IMPORTANCE. /ORGANOPHOSPHORUS PESTICIDES/|THE PROTECTIVE CLOTHING SHOULD BE KEPT IN SEPARATE PLACES WHERE IT CANNOT BE CONTAMINATED WITH TOXIC CHEMICALS. IT SHOULD BE FORBIDDEN TO KEEP THIS CLOTHING IN LIVING QUARTERS. PROTECTIVE CLOTHING MUST BE WASHED AT LEAST ONCE A WEEK AND EACH TIME IT IS CONTAMINATED WITH PESTICIDES. BEFORE WASHING THE CLOTHING SHOULD BE SOAKED FOR SEVERAL HOURS IN A CALCIUM CARBONATE SOLUTION. /PESTICIDES/
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.
Toxicity
highly toxic
ANTICHOLINESTERASE (ORGANOPHOSPHORUS) INSECTICIDES ANTAGONIZE POLARIZING MUSCLE RELAXANTS. PHENOTHIAZINES /AND THIOXANTHENES/: ... MAY ENHANCE TOXIC EFFECTS OF ORGANOPHOSPHORUS INSECTICIDES. /INSECTICIDES, ORGANOPHOSPHORUS/
LD50 Rat male oral 52-170 mg/kg|LD50 Mice oral 210-550 mg/kg|LD50 Rabbit percutaneous 100-600 mg/kg
... /Individuals with the following medical conditions/: ... diseases of the central nervous system, mental disorders & epilepsy, pronounced endocrine & vegetative disorders, pulmonary tuberculosis, bronchial asthma, chronic respiratory diseases, cardiovascular diseases & circulatory disorders, gastrointestinal diseases (peptic ulcer), gastroenterocolitis, diseases of liver & kidneys, eye diseases (chronic conjunctivitis & keratitis). ... /Organophosphorus pesticides/
Bromophos-ethyl's production and former use(1) as an insecticide, acaricide, larvicide(2), and miticide and in the use of controlling public health pests(3) may have resulted in its direct release to the environment(SRC).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 54,000(SRC), determined from a log Kow of 6.15(2) and a regression-derived equation(3), indicates that bromophos-ethyl is expected to be immobile in soil(SRC). Volatilization of bromophos-ethyl from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.6X10-5 atm-cu m/mole(4), using a fragment constant estimation method(4). Bromophos-ethyl is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 4.60X10-5 mm Hg(5).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 54,000(SRC), determined from a log Kow of 6.15(2) and a regression-derived equation(3), indicates that bromophos-ethyl is expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 1.6X10-5 atm-cu m/mole(4), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 73 hrs and 40 days, respectively(SRC). However, the volatilization half-life does not take into account the effects of adsorption. An estimated KOC of 54,000(SRC) from a log Kow of 6.15(2) and a regression-derived equation(3), suggests that volatilization could be attenuated by adsorption to suspended solids and sediments in water(SRC). This is apparent from the results of two EXAMS model runs, one in which the effect of adsorption was considered, yielding an estimated half-life of 25 years in a model pond 2 m deep, and one in which the effects of adsorption was ignored, yielding an estimated half-life of 51 days in a model pond 2 m deep(7). According to a classification scheme(5), an estimated BCF of 1.0X10+4(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is very high.|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), bromophos-ethyl, which has a vapor pressure of 4.60X10-5 mm Hg at 30 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase bromophos-ethyl 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 4 hrs(SRC), calculated from its rate constant of 9.0X10-11 cu cm/molecule-sec at 25 °C(3) determined using a structure estimation method(3). Particulate-phase bromophos-ethyl may be removed from the air by wet and dry deposition(SRC).
The rate constant for the vapor-phase reaction of bromophos-ethyl with photochemically-produced hydroxyl radicals has been estimated as 9.0X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 4 days(SRC) at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1).
An estimated BCF of 1.0X10+4 was calculated for bromophos-ethyl(SRC), using a log Kow of 6.15(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is very high.
The Koc of bromophos-ethyl is estimated as 54,000(SRC), using a log Kow of 6.15(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that bromophos-ethyl is expected to be immobile in soil.
The Henry's Law constant for bromophos-ethyl is estimated as 1.6X10-5 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that bromophos-ethyl is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 73 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 40 days(SRC). However, the volatilization half-life does not take into account the effects of adsorption. This is apparent from the results of two EXAMS model runs, one in which the effect of adsorption was considered, yielding an estimated half-life of 25 years in a model pond 2 m deep, and one in which the effects of adsorption was ignored, yielding an estimated half-life of 51 days in a model pond 2 m deep(4). Bromophos-ethyl's Henry's Law constant(1) indicates that volatilization from moist soil surfaces may occur(SRC). Bromophos-ethyl is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 4.60X10-5 mm Hg at 30 °C(3).
Bromophos-ethyl was qualitatively identified in raw agricultural commodities during FY83-86 according to the FDA's program for monitoring pesticides in foods(1).
Occupational exposure to bromophos-ethyl may have occurred through inhalation of vapors and via eye(1) and dermal contact with this compound at workplaces where bromophos-ethyl was produced or used(SRC). The general population may have been exposed due to its former use(3) in controlling public health pests(2).
The level of 4-(iso-propylamino)diphenylamine in the urine of rubber vulcanization workers were noted to be higher in the end-shift than in the before-shift sample, respective concentrations being 83.57 and 19.55 ug/l(1).
Drug Information
The rate of dermal absorption /of organophosphorus pesticides/ may be ... influenced by the solvent used. /Organophosphorus pesticides/|... The organophosphorus insecticides are, in contrast to the chlorinated insecticides, rapidly metabolized & excreted and are not appreciably stored in body tissues. /Organophosphorus insecticides/|Many of the organophosphorus insecticides are excreted in the milk ... /Organophosphorus insecticides/|Following their absorption, most organophosphorus cmpd are excreted ... as hydrolysis products in the urine. /Anticholinesterase agents/|For more Absorption, Distribution and Excretion (Complete) data for BROMOPHOS-ETHYL (6 total), please visit the HSDB record page.
Plasma & tissue enzymes are responsible for hydrolysis /of organophosphorus compounds/ to the corresponding phosphoric & phosphonic acids. However, oxidative enzymes are also involved in the metabolism of some organophosphorus compounds. /Anticholinesterase agents/|The organophosphorus anticholinesterase agents are hydrolyzed in the body by a group of enzymes known as A-esterases or paroxonase. The enzymes are found in plasma and in the hepatic endoplasmic reticulum & can hydrolyze a large number of organophosphorus compounds ... by splitting the anhydride, P-F, P-CN, or ester bond. /Anticholinesterase agents/|Bromophos was enzymatically degraded to 4-bromo-2,5-dichlorophenyl phosphorothionate. This was the only product formed when hog or mouse liver preparations were used. Glutathione stimulated the reaction. When incubated with 4 molor sodium hydroxide, dimethyl phosphorothionate formed. No desmethyl bromophos was observed. When incubated with buffers of pH 10 and 11, the aryl phosphorothionate did form. /Bromophos/|The oxon of bromophos was hydrolyzed rather slowly by plasma of sheep, rabbit, rat, and chicken. /Bromophos/|Analyses of meat fats of animals from areas that use bromophos-ethyl dips and sprays to control cattle ticks have detected a residue identified as O,O-diethyl O-(2,5-dichlorophenyl)phosphorothionate.
Organophosphorus derivatives act by combining with and inactivating the enzyme acetylcholinesterase (AChE). ... The inactivation of cholinesterase by cholinesterase inhibitor pesticides allows the accumulation of large amounts of acetylcholine, with resultant widespread effects that may be ... separated into 4 categories: (1) Potentiation of postganglionic parasympathetic activity. ... (2) Persistent depolarization of skeletal muscle ... (3) Initial stimulation followed by depression of cells of central nervous system ... (4) Variable ganglionic stimulation or blockade ... /Cholinesterase inhibitor pesticides/|The main feature of the toxic mechanism of organophosphorus pesticides is inhibition of the esterase enzyme activity, in particular of cholinesterase, which plays an important physiological part. Organophosphorus pesticides can also indirectly interact with the biochemical receptors of acetylcholine. /Organophosphorus pesticides/
Airway protection. Insure that a clear airway exists. Intubate the patients 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, so as to minimize the risk of ventricular fibrillation. In severe poisonings, it may be necessary to support pulmonary ventilation mechanically for several days. /Organophosphate pesticides/|Atropine sulfate. 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 if difficult to obtain. Depending on the severity of poisoning, doses of atropine ranging from very low to as high as 300 mg/day may be required, or even continuous infusion. 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 disposition of organophosphate. Recrudescence of poisoning may occur if tissue concentrations of organophosphate remain high when the effect of atropine wears off. Atropine is effective against muscarinic manifestations, but it is ineffective against nicotinic actions, specifically muscle weakness and twitching, and respiratory depression. Despite the limitations, atropine is often a life-saving agent in organophosphate poisonings. Favorable response to a test dose of atropine (1 mg in adults, 0.01 mg/kg in children under 12 years) can help differentiate poisoning by anticholinesterase agents from other conditions. However, lack of response, with no evidence of atropinization (atropine refractoriness) is typical of more severe poisonings. The adjunctive use of nebulized atropine has been reported to improve respiratory distress, decrease bronchial secretions, and increase oxygenation. /Organophosphate pesticides/|Glycopyrolate has been studied as an alternative to atropine and found to have similar outcomes using continuous infusion. Ampules of 7.5 mg of glycopyrolate were added to 200 ml of saline and this infusion was titrated to the desired effects of dry mucous membranes and heart rate above 60 beats/min. During this study, atropine was used as a bolus for a heart rate less than 60 beats/min. The other apparent advantage to this regimen was a decreased number of respiratory infections. This may represent an alternative when there is a concern for respiratory infection due to excessive and difficult to control secretions, and in the presence of altered level of consciousness where the distinction between atropine toxicity or relapse of organophosphate poisoning is unclear. /Organophosphate pesticides/|Pralidoxime. Before administration of pralidoxime, draw a blood sample (heparinized) for cholinesterase analysis (since pralidoxime tends to reverse the cholinesterase depression). Administer pralidoxime (Protopam, 2-PAM), a cholinesterase reactivator, in cases of severe poisoning by organophosphate pesticides in which respiratory depression, muscle weakness, and/or twitching are severe. When administered early (usually less than 48 hours after poisoning) pralidoxime relieves the nicotinic as well as the muscarinic effects of poisoning. Pralidoxime works by reactivating the cholinesterase and also by slowing the "aging" process of phosphorylated cholinesterase to a non-reactivatable form. ... Dosage of pralidoxime may be repeated in 1-2 hours, then at 10-12 hour intervals if needed. In very severe poisonings, dosage rates may be doubled. Repeated doses of pralidoxime are usually required. In cases that involve continuing absorption of organophosphate (as after ingestion of large amounts), or continuing transfer of highly lipophilic organophosphate from fat into blood, it may be necessary to continue administration of pralidoxime for several days beyond the 48 hour post-exposure interval usually cited as the limit of its effectiveness. ... Blood pressure should be monitored during administration because of the occasional occurrence of hypertensive crisis. Administration should be slowed or stopped if blood pressure rises to hazardous levels. Be prepared to assist pulmonary ventilation mechanically if respiration is depressed during or after pralidoxime administration. If intravenous injection is not possible, pralidoxime may be given by deep intramuscular injection. /Organophosphate pesticides/|For more Antidote and Emergency Treatment (Complete) data for BROMOPHOS-ETHYL (15 total), please visit the HSDB record page.
All the organophosphorus insecticides have a cumulative effect by progressive inhibition of cholinesterase ... /Organophosphorus insecticides/|The symptoms of chronic poisoning due to organophosphorus pesticides include headache, weakness, feeling of heaviness in head, decline of memory, quick onset of fatigue, disturbed sleep, loss of appetite, & loss of orientation. Psychic disorders, nystagmus, trembling of the hands & other nervous system disorders can be observed in certain cases. Sometimes neuritis, paresis & paralysis develop. /Organophosphorus pesticides/|Toxic effects may include anorexia, abdominal cramps, nausea, vomiting, diarrhea, incontinence, eye changes, weakness, dyspnea, bronchospasm, lacrimation, increased salivation & sweating, bradycardia, hypotension or hypertension due to asphyxia, cyanosis, & muscular twitching of the eyelids, tongue, face, & neck, possibly progressing to convulsions. Central nervous system symptoms include restlessness, anxiety, dizziness, drowsiness, tremor, ataxia, depression, confusion, & coma. Death may occur from depression of the respiratory or cardiovascular system. Neuropathy appears to be a rare problem with the organophosphorus insecticides now in use. /Organophosphorus insecticides/|Organophosphate insecticides ... are potent cholinesterase enzyme inhibitors that act by interfering with the metabolism of acetylcholine, which results in accumulation of acetylcholine at neuroreceptor transmission sites. Exposure produces a broad spectrum of clinical effects indicative of massive overstimulation of the chlorinergic system, including muscarinic effects (parasympathetic), nicotinic effects (sympathetic and motor), and CNS effects. These effects present clinically as feeling of headache, weakness, dizziness, blurred vision, psychosis, respiratory difficulty, paralysis, convulsions, and coma. Typical findings are given by the mnemonic "SLUD." which stands for salivation, lacrimation, urination, and defecation. A small percentage of patients may fail to demonstrate miosis, a classic diagnostic hallmark. Onset of clinical manifestation of organophosphate poisoning usually occurs within 12 hours of exposure. /Organophosphate insecticides/|For more Human Toxicity Excerpts (Complete) data for BROMOPHOS-ETHYL (6 total), please visit the HSDB record page.
ethyl bromophos
Bromophos-ethyl Use and Manufacturing
For Bromophos-ethyl (USEPA PC Code 214500) there are 0 labels match./SRP: Not registered for current use in the U.S./|Acaricide, insecticide, larvicide /Former use/|Control of Diptera, Hemiptera, some Lepidoptera, Coleoptera, some other insects, and mites in fruit, vegetables, field crops, ornamentals, and forestry. Also used in public health for control of flies, mosquito larvae, etc; for control of insects in animal houses; and as an animal ectoparasiticide. /former uses/
Trade Names: Filariol, Nexagan.|Emulsifiable concentrate; wettable powder; granules; cold fogging concentrate; ultra-low vol liquid.|Emulsifiable concentrate (400 or 800 g ai/l), wettable powder (250 g/kg); granules (50 g/kg); cold fogging concentrate (800-900 g/l); animal dips (400 g/l).
Discontinued by Shell Agrar GmbH & Co KG|... Compatible with other pesticides except sulfur and organometal fungicides.|Material believed to be no longer manufactured, or marketed for crop protection use
Product analysis is by infrared spectrometry or by titrimetric methods. Residues may be determined by gas liquid chromatography. Determination of the halogenated phenol produced by hydrolysis can be used for both product and residue analysis.|Analysis of products by oxidation with bromide-bromate solution, and titration of the excess bromate with sodium thiosulphate.|Analysis of residues by gas liquid chromatography with phosphorus-specific flame ionization detector.|FDA Method 212.1. Organochlorine Residues (Nonionic) General Method for Nonfatty Foods Including Acetonitrile Extraction, Water/Acetonitrile Extraction, Aqueous Acetonitrile to Petroleum Ether Transfer, and Florisil Column Cleanup.|For more Analytic Laboratory Methods (Complete) data for BROMOPHOS-ETHYL (6 total), please visit the HSDB record page.
Agrochemicals -> Insecticides
Computed Properties
Molecular Weight:394.0
XLogP3:6.1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:6
Exact Mass:391.88052
Monoisotopic Mass:391.88052
Topological Polar Surface Area:59.8
Heavy Atom Count:18
Complexity:301
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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