470-90-6CCOP(=O)(OCC)OC(=CCl)c1ccc(Cl)cc1ClFSAVDKDHPDSCTO-UHFFFAOYSA-NChlorfenvinphos is an insecticide that is a colorless liquid with a mild odor. It was commonly used until 1991 when all products containing chlorfenvinphos as an active ingredient were canceled in the United States. Commercial preparations commonly sold in stores were usually 90% chlorfenvinphos. Most of the chlorfenvinphos used was in liquid form. Chlorfenvinphos was widely used to control household pests such as flies, fleas, and mice. The chemical is manufactured and does not occur naturally in the environment. It was sold under common trade names including Birlane®, Dermaton®, Sapercon®, Steladone®, and Supona®. Use of trade names is for identification only and does not imply endorsement by the Agency for Toxic Substances and Disease Registry, the Public Health Service, or the U.S. Department of Health and Human Services.
470-90-6DTXSID7034250CHEMBL2104653、CHEMBL2354650Insecticides
Active substance -> EU Pesticides database: Not approved
Pesticides -> Organophosphate Insecticides
Veterinary substances, Acaricides, Insecticides
log Kow = 3.81
3.82
1.36 at 59.9 °F (EPA, 1998) - Denser than water; will sink
1.36 g/cu cm @ 20 °C
Relative density (water = 1): 1.36
1.36 @ 20°C
Colorless liquid
Yellowish liquid
Amber-colored liquid
Miscible with most common organic solvents, e.g. acetone, ethanol, kerosene, xylene, propylene glycol, dichloromethane, hexane.
In water, 124 mg/l at 20 °C
Solubility in water: none
安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。
Danger
H300: Fatal if swallowed [Danger Acute toxicity, oral]
P262, P264, P270, P273, P280, P301+P316, P302+P352, P316, P321, P330, P361+P364, P391, P405, and P501 (click each P-code to see the statement)
Danger
H300+H330 (21.1%): Fatal if swallowed or if inhaled [Danger Acute toxicity, oral; acute toxicity, inhalation]
P260, P262, P264, P270, P271, P273, P280, P284, P301+P316, P302+P352, P304+P340, P316, P320, P321, P330, P361+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Hazard Traits - Neurotoxicity
Chlorfenvinphos: HSNO Approval: HSR003564 Approved with controls
The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)
(Non-Specific -- Organophosphorus Pesticide, Liquid, n.o.s.) This material may burn but does not ignite readily. Container may explode in heat of fire. Fire and runoff from fire control water may produce irritating or poisonous gases. Avoid iron, steel, and brass. Stable when stored in glass or polyethylene lined containers. Avoid alkaline aqueous solutions. (EPA, 1998)
Combustible. Liquid formulations containing organic solvents may be flammable. Gives off irritating or toxic fumes (or gases) in a fire.
... CHLORFENVINPHOS ... /IS/ DETOXIFIED IN MAMMALS EXTENSIVELY BY O-DEALKYLATION.
MICROSOMES FROM RABBIT LIVERS WERE INCUBATED WITH CHLORFENVINPHOS. OXIDATIVE CLEAVAGE OF ESTER BOND ... /OCCURRED/ VIA HYDROXYLATION ... TO GIVE 1-HYDROXYETHYL PHOSPHATE TRIESTER. THIS ... INTERMEDIATE BROKE DOWN ... TO 2-CHLORO-1-(2,4-DICHLOROPHENYL) VINYL ETHYL HYDROGEN PHOSPHATE. OXIDATIVE CLEAVAGE OF THE C-O BOND, RATHER THAN HYDROLYSIS OF THE P-O BOND, YIELDED ACETALDEHYDE ... .
AFTER ORAL ADMIN TO RATS AND DOGS...IN RATS, 32.3% OF DOSE WAS ACCOUNTED FOR BY 2-CHLORO-1-(2,4-DICHLOROPHENYL) VINYL MONOETHYL PHOSPHATE; 41% BY 1-(2',4'-DICHLOROPHENYL) ETHYL BETA-D-GLUCOPYRANOSIDURONIC ACID; 7% BY 2,4-DICHLOROMANDELIC ACID; 2.6% BY 2,4-DICHLOROPHENYLETHANEDIOL GLUCURONIDE; AND 4.3% BY 2,4-DICHLOROHIPPURIC ACID. IN DOGS THIS WAS 69.6% 2-CHLORO-1-(2,4-DICHLOROPHENYL) VINYL MONOETHYL PHOSPHATE; 3.6% 1-(2',4'-DICHLOROPHENYL) ETHYL BETA-D-GLUCOPYRANOSIDURONIC ACID; 13.4% /UNIDENTIFIED COMPD/; 2.7% 2,4-DICHLOROPHENYLETHANEDIOL GLUCURONIDE. AFTER IV ADMINISTRATION, CHLORFENVINPHOS WAS RAPIDLY METABOLIZED TO O-DESETHYL ANALOG (2-CHLORO-1-(2,4-DICHLOROPHENYL) VINYL MONOETHYL PHOSPHATE) (83%), 2,4-DICHLOROMANDELIC ACID (9%), AND 1-(2',4'-DICHLOROPHENYL) ETHYL BETA-D-GLUCOPYRANOSIDURONIC ACID (8%) IN DOGS.
One metabolite of chlorfenvinphos in humans is desethyl chlorvinphos.
For more Metabolism/Metabolites (Complete) data for CHLOROFENVINPHOS (6 total), please visit the HSDB record page.
Drugs that inhibit cholinesterases. The neurotransmitter ACETYLCHOLINE is rapidly hydrolyzed, and thereby inactivated, by cholinesterases. When cholinesterases are inhibited, the action of endogenously released acetylcholine at cholinergic synapses is potentiated. Cholinesterase inhibitors are widely used clinically for their potentiation of cholinergic inputs to the gastrointestinal tract and urinary bladder, the eye, and skeletal muscles; they are also used for their effects on the heart and the central nervous system.
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.
A pesticide or chemical agent that kills mites and ticks. This is a large class that includes carbamates, formamides, organochlorines, organophosphates, etc, that act as antibiotics or growth regulators.
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読み込み中…
333 to 338 °F at 0.5 mmHg (EPA, 1998)
Amber liquid; bp: 167-170 °C at 0.5 mm Hg /Technical chlorfenvinphos/
at 0.07kPa: 167-170 °C
-9 to -2 °F (EPA, 1998)
-23 to -19 °C
-19 - -23 °C
-23 °C
Chlorfenvinphos is an insecticide that is a colorless liquid with a mild odor. It was commonly used until 1991 when all products containing chlorfenvinphos as an active ingredient were canceled in the United States. Commercial preparations commonly sold in stores were usually 90% chlorfenvinphos. Most of the chlorfenvinphos used was in liquid form. Chlorfenvinphos was widely used to control household pests such as flies, fleas, and mice. The chemical is manufactured and does not occur naturally in the environment. It was sold under common trade names including Birlane®, Dermaton®, Sapercon®, Steladone®, and Supona®. Use of trade names is for identification only and does not imply endorsement by the Agency for Toxic Substances and Disease Registry, the Public Health Service, or the U.S. Department of Health and Human Services.
The average of two baseline respective cholinesterase activity determinations three days apart, with no exposures to enzyme inhibiting pesticides for at least 30 days, is recommended for each worker prior to exposure to cholinesterase inhibitors because of large inter-individual differences in published baseline values. To be established at least once a year. Removal from workplace exposures is recommended until the cholinesterase activity returns to within 20% of baseline. [TLVs and BEIs]
Toxicology Review: Residue Reviews 46: 1 (1973)
Toxicology Review: Cahiers de Nutrition et de Dietetique 10 (3): 43 (1975)
Toxicology Review: Residue Reviews 63: 1 (1976)
As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA, as amended in 1988, were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Chlorfenvinphos is found on List B. Case No: 2090; Pesticide type: Insecticide; Case Status: No products containing the pesticide are actively registered ... The case /is characterized/ as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.; Active ingredient (AI): 2-chloro-1-(2,4-dichlorophenyl)vinyl diethyl phosphate; AI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled."
(Non-Specific -- Organophosphorus Pesticide, Liquid, n.o.s.) Move container from fire area if you can do it without risk. Fight fire from maximum distance. Dike fire control water for later disposal; do not scatter the material. Wear positive pressure breathing apparatus and special protective clothing.
Use water spray, powder, alcohol-resistant foam, carbon dioxide.
Fresh air, rest. Artificial respiration may be needed. Refer for medical attention.
Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
Induce vomiting (ONLY IN CONSCIOUS PERSONS!). Refer for medical attention .
Biological Exposure Indices (BEI) [ACGIH] - Acetylcholinesterase activity in red blood cells = 70% of individual's baseline; Butylcholinesterase activity in serum or plasma = 60% of individual's baseline; Sample at end of shift; [TLVs and BEIs]
IT IS STABLE WHEN STORED IN GLASS OR POLYETHYLENE-LINED CONTAINERS...
Do not contaminate feed or foodstuffs ... . Keep container closed.
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.
Hydrolysis & landfill: Chlorfenvinphos should be treated by alkali and then mixed with a portion of soil which is rich in organic /matter/. (Peer-review conclusions of an IRPTC expert consultation (May 1985))
Personal protection: chemical protection suit including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Collect leaking and spilled liquid in sealable containers as far as possible. Do NOT wash away into sewer. Carefully collect remainder. Then store and dispose of according to local regulations.
Do not drink any alcoholic beverages before or during spraying since alcohol promotes absorption of organic phosphates.
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.
LD50 Anas platyrhynchos (Mallard) oral 85.5 mg/kg (95% confidence limit 44.5-164 mg/kg), 3-4 mo old females /91% beta, 8% alpha isomers/
LD50 Colinus virginianus (Bobwhite) oral 80.0-160 mg/kg, 12 mo old males /91% beta, 8% alpha isomers/
LD50 (Pheasant) oral 63.5 mg/kg (95% confidence limit 45.8-88.1 mg/kg), 3-4 mo old females /81% beta, 8% alpha isomers/
LC50 Rasbora heteromorpha (Harlequin fish) 0.27 mg/l/48 hr /Conditions of bioassay not specified/
LC50 Libistes reticulatus (Guppy) 0.53 mg/l/48 hr /Conditions of bioassay not specified/
TERRESTRIAL FATE: Based on a classification scheme(1), a Koc of 295 in silt loam soil (containing 3.53% organic matter)(2), indicates that chlorofenvinphos is expected to have moderate mobility in soil(SRC). Volatilization of chlorofenvinphos from moist soil surfaces is not expected to be an important fate process(3) given an estimated Henry's Law constant of 2.9X10-8 atm-cu m/mole(SRC) derived from its vapor pressure, 7.5X10-6 mm Hg(4), and water solubility, 124 mg/l(5). Chlorofenvinphos is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). The persistence half-lives for chlorofenvinphos ranged from about 14 days to >150 days in soil(6-13). The initial half-live of chlorofenvinphos in soils varied from 2 wks to more than 23 wks depending on the soil type, the formulation, and the dosage level(6).
AQUATIC FATE: Based on a classification scheme(1), a Koc of 295 in silt loam soil (containing 3.53% organic matter)(2), indicates that chlorofenvinphos is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2.9X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 7.5X10-6 mm Hg(4), and water solubility, 124 mg/l(5). According to a classification scheme(6), an estimated BCF of 28(SRC), from a log Kow of 3.81(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). The persistence half-lives for chlorofenvinphos in samples of Limon River water under filtered-dark, filtered/sunlight, non-filtered/open, and non-filtered closed conditions were 51.2, 23.8, 13.2, and 21.7 days, respectively(9). The filtered-dark sample was limited to only chemical and biodegradation and had the longest half-life (ie, 51.2 days); whereas the non-filtered/open sample, in which chlorofenvinphos disappeared by volatilization and adsorption as well as chemical and biological degradation, had the shortest half-life (ie, 13.2 days)(9). Chlorofenvinphos hydrolyzes slowly in neutral, acidic and slightly alkaline solution; and it hydrolyzes rapidly in strongly alkaline solutions(4). Half-lives for chlorofenvinphos were >700 hrs at pH 1.1, >400 hrs at pH 9.1 (at 38 °C)(4). The hydrolysis half-life at pH 13 was 1.3 hrs (at 20 °C)(4).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), chlorofenvinphos, which has a vapor pressure of 7.5X10-6 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere(SRC). Vapor-phase chlorofenvinphos is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals and ozone(SRC); the half-life for reaction with hydroxyl radicals in air is estimated to be 7 hrs(SRC), calculated from its rate constant of 5.78X10-11 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3); the half-life for reaction with ozone in air is estimated to be 92 hrs(SRC), calculated from its rate constant of 3.00X10-18 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3). Particulate-phase chlorofenvinphos may be removed from the air by wet and dry deposition(SRC).
Chlorofenvinphos has been detected, by FDA's Pesticide Residue Monitoring Program, in US foods during fiscal years 1978-1990(1-4); however, the concns and the frequencies of occurrence were not reported(1-4). In a US monitoring survey of 6,970 produce samples (fruits and vegetables) collected between 1989 and 1991, chlorofenvinphos was detected (detection limit of 0.75 ppm) on only one sample (tomato)(5). In Thailand between 1987-89, the concn of chlorofenvinphos in various vegetables was 0.47 mg/kg(6). As part of the Belgian Total Diet Study in 1991-3, chlorofenvinphos was found in steamed carrots at concn of <0.05 ppm (3 samples) and 0.05-0.1 (3 samples)(7). In Canada between 1992-94, chlorofenvinphos was measured in grapes(fresh), oranges(fresh), peppers, and pineapples at concns: <0.05 ppm (3 sample); 0.05-0.10 ppm and 0.1-0.5 ppm (2 and 1 sample(s)); <0.05 ppm and 0.05-0.10 ppm (1 and 1 sample); and 0.05-0.10 ppm (1 sample), respectively(8). Crops from field trials in the UK and Germany between the years 1963-1964 were analyzed for residues of chlorofenvinphos(9). Residues in turnips, cabbages, potatoes, and white radish were less than 0.05 ppm when harvested 8-29 wks after soil applications at 4-8 lbs/acre(9). Residues in carrots were generally less than 0.05 ppm but were near 0.1 ppm in some nature carrots harvested from soil 17-26 wks after application of granules at 8 lbs/acre(9).
In the Region of Murcia (Spain), the calculated daily ingestion of chlorofenvinphos in citrus fruits, and pitted and seedy fruits tested in 1985-86 and 1989 (values for 1989 in parentheses) were 413 (288) and 0.8 (25.7) mg/kg body wt, respectively(1). In Rome, Italy between 1980-4, the avg daily intake of E- and Z- chlorofenvinphos was 0.05 and 0.46 ug/day per person(2).
Pupillary constriction, muscle cramp, excessive salivation. Sweating. Nausea. Dizziness. Laboured breathing. Headache. Convulsions. Unconsciousness. Symptoms may be delayed.
MAY BE ABSORBED! See Inhalation.
Blurred vision.
Abdominal cramps. Diarrhoea. Vomiting. Weakness. Convulsions. See Inhalation.
The substance is very toxic to aquatic organisms. The substance may cause long-term effects in the aquatic environment. This substance does enter the environment under normal use. Great care, however, should be taken to avoid any additional release, for example through inappropriate disposal.
As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA, as amended in 1988, were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Chlorfenvinphos is found on List B. Case No: 2090; Pesticide type: Insecticide; Case Status: No products containing the pesticide are actively registered ... The case /is characterized/ as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.; Active ingredient (AI): 2-chloro-1-(2,4-dichlorophenyl)vinyl diethyl phosphate; AI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled."
Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Chlorofenvinphos is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 500 lbs.
PEAK CONCN OF RADIOACTIVE MATERIAL IN URINE OF STEERS, AFTER SPRAY APPLICATION OF (32)P-LABELED CHLORFENVINPHOS, OCCURRED IN SAMPLES AT 3 HR POST-TREATMENT. ... RESIDUES OF CHLORFENVINPHOS ... WERE BELOW LIMITS OF DETECTION IN ORGANS OF EXPOSED SHEEP. RESIDUE LEVELS NEVER REACHED 0.1 PPM. AFTER ORAL ADMIN TO RATS & DOGS, (14)C CHLORFENVINPHOS WAS RAPIDLY METABOLIZED AND EXCRETED. ABOUT 90% WAS ELIMINATED IN URINE; REMAINDER, VIA FECES AND, TO A LESSER EXTENT, VIA EXPIRED GASES. ... STUDIES HAVE SHOWN THAT THIS COMPD REACTED WITH AND WAS BOUND BY PROTEINS IN BLOOD PLASMA OF MAMMALS AND IN HOMOGENATES OF HOUSE FLY HEADS.
Dosage levels of 112 mg/hr/man /applied to left forearm/ ... produced blood levels of 0.012 ppm or more measured 24 hr after exposure. ... 70.8 mg/hr/man caused ... a blood level of 0.006 ppm 24 hr after exposure.
Oral dosages as high as 1 mg/kg did not affect cholinesterase or the awake-sleep cycle of rats. At dosages over 2 mg/kg, the cholinesterase activities of both brain & red cells were significantly decr, & the spontaneous EEG showed a prominent arousal pattern with suppression of curves characteristic of sleep. Maximal inhibition of brain cholinesterase occurred 3 hr after dosing & lasted for more than 72 hr.
Used to control insect pests on livestock. Used in the past to kill household flies, fleas, and mites. [ATSDR PHS]
Farming (Pesticides) [Category: Industry]
For Chlorofenvinphos (USEPA/OPP Pesticide Code: 084101) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./
Cholinesterase inhibitor; insecticide and acaricide; used in public health for control of mosquito larvae. Animal ectoparasitcide /Former use/
/IT IS USED/ AGAINST TICKS AND FLIES ON ... HORSES, GOATS AS WELL AS ... FLEAS ON DOGS, AND ON ORGANIC WASTES AND BREEDING PLACES OF FLY LARVAE INCLUDING DAIRYBARNS. ... DO NOT USE ON CATS.
Nematocide /Former use/
USEPA/OPP Pesticide Code 084101; Trade Names: Compound 4072, Supona, Birlane, GC-4072, SD 7859, Birlane 10 G, Clofenvineosum, Dermaton, General chemical compound GC-4072, Shell 4072, Supone ,Vinylphate, Unitox, Apachlor, Steladone, C 8949, CGA 26351, ENT 24969, OMS 1328.
DUSTS 5%, PELLETIZED GRANULES 10%; WETTABLE POWDERS 25%; EMULSIFIABLE CONCENTRATES 24%; SEED DRESSINGS 40% + 2% MERCURY CMPD. SAPECRON 10G AND STELADONE 300 EC ... BIRLANE REFERS TO MIXT OF ISOMERS OF 2-CHLORO-1-(2,4-DICHLOROPHENYL) VINYL DIETHYL PHOSPHATE.
Tech grade (greater than equal 90% Z- and E- isomers), typical ratio (Z):(E) 8.6:1
Mixtures: (chlorofenvinphos +) cypermethrin; cypermethrin + methoxychlor; alpha-cypermethrin; dimethoate; methoxychlor; oxamyl; phenol; petroleum oils.
Formulations: Emulsifiable concentrates, granules, seed treatments, wettable powder
Chemical Classes -> Organophosphates and carbamates
Veterinary substances, Acaricides, Insecticides
INSECTICIDES
Introduced into the United States in 1963 by the Shell Int Chem Co Lts, Ciba AG (now Ciba- Geigy AG), and by Allied Chemical Corp. The Burroughs-Wellcome Co produced several chlorofenvinphos-containing formulated products. Other former producers include American Cyanamid Co.