64-00-6CNC(=O)Oc1cccc(C(C)C)c1GYKXQTKSWLAUIT-UHFFFAOYSA-NPure white solid without appreciable odor. Used as an insecticide to protect cotton, fruit, vegetables and field crops. Not registered as a pesticide in the U.S. (EPA, 1998)
64-00-6log Kow = 2.63
2.63
10% in isophorone; 10% in xylene; 20% in toluene; 20% in toluene; 40% in isopropanol; 50% in acetone; 60% in dimethylformamide. Practically insoluble in cyclohexane.
In water, 85 ppm at 30 °C
In water, 270 mg/L at 25 °C /Estimated/
162 to 165 °F (EPA, 1998)
72 to 74 °C
0.00439 [mmHg]
4.4X10-3 mm Hg at 25 °C /Estimated/
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Danger
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
P262, P264, P270, P280, P301+P316, P302+P352, P316, P321, P330, P361+P364, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 3 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Applicators and villagers poisoned from spraying 5% solution had symptoms including weakness, headache, miosis, and profuse perspiration; Half of the males (17 of 34) developed skin eruptions; Inhalation of dust at 45 mg/m3 caused 75% decrease in brain cholinesterase activity in rats; [HSDB] A cholinesterase inhibitor; [CAMEO] See CARBAMATE INSECTICIDES.
All of the insecticidal carbamates are cholinergic ... The compounds are strong carbamylating inhibitors of cholinesterase & may have direct action on acetylcholine receptors because of their pronounced structural resemblance to acetylcholine. The importance of structural complementarity is shown by the difference in the o-, m-, & p-isopropylphenyl N-methylcarbamates.
The carbamates alone weakly activated estrogen- or progesterone-responsive reporter genes in breast and endometrial cancer cells. All of the carbamates decreased estradiol- or progesterone-induced reporter gene activity in the breast and endometrial cancer cells. In whole cell competition binding assays, the carbamates demonstrated a limited capacity to displace radiolabeled estrogen or progesterone from /estrogen receptor/ or /progesterone receptor/. /Carbamates/
Carbamates are effective insecticides by virtue of their ability to inhibit acetylcholinesterase (AChE) in the nervous system. They also inhibit other esterases. The carbamylation of the enzyme is unstable, and the regeneration of AChE is relatively rapid compared with that from a phosphorylated enzyme. Thus, carbamate pesticides are less dangerous with regard to human exposure than organophosphorus pesticides. The ratio between the dose required to produce death and the dose required to produce minimum symptoms of poisoning is substantially larger for carbamate compounds than for organophosphorus compounds. /Carbamate Pesticides/
The carbamate insecticides are reversible cholinesterase-inhibitors. They cause this effect by reversible carbamylation of the enzyme acetylcholinesterase, allowing accumulation of acetylcholine, as with the organophosphate insecticides. ... While the organophosphate insecticides cause irreversible inhibition of the cholinesterase enzymes, the carbamyl-enzyme complex is reversible & dissociates far more readily than the organophosphate complex. The clinical syndrome is more benign & of much shorter duration with the carbamate insecticides. /Carbamate insecticides/
When rats were exposed to labeled UC-10854, labeled (14)C-carbon dioxide was formed. After incubation of rat liver microsomes with UC-10854 in the presence of reduced nicotinamide--adenine dinucleotide phosphate (NADPH), 3-(1-hydroxy-1-methylethyl)phenyl methylcarbamate & 3-isopropyl N-hydroxymethylcarbamate were observed. Several unidentified compounds were also found.
Wird geladen…
DTXSID1040324CHEMBL20468190.4 [mm Hg] @25 °C
Pure white solid without appreciable odor. Used as an insecticide to protect cotton, fruit, vegetables and field crops. Not registered as a pesticide in the U.S. (EPA, 1998)
White odorless solid; [HSDB]
P202; As stipulated in 40 CFR 261.33, when m-cumenyl methylcarbamate, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to federal and/or state hazardous waste regulations. Also defined as a hazardous waste is any container or inner liner used to hold this waste or any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5(e)).
PHENOL, 3-(1-METHYLETHYL)-, METHYLCARBAMATE 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.
Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 1 lb. The toll free number of the NRC is (800) 424-8802; In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).
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. Phenol, 3-(1-methylethyl)-, methylcarbamate is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 500 or 10,000 lbs. Extremely hazardous substances that are solids are subject to either of two threshold planning quantities ... The lower quantity applies only if the solid exists in powdered form and has a particle size less than 100 microns; or is handled in solution or in molten form; or meets the criteria for a National Fire Protection Association (NFPA) rating of 2, 3 or 4 for reactivity. If the solid does not meet any of these criteria, it is subject to the upper ... threshold planning quantity ... .
(Non-Specific -- Carbamate Pesticide, Solid, n.o.s.) Wear positive pressure breathing apparatus and special protective clothing. Move container from fire area if you can do it without risk. Dike fire control water for later disposal; do not scatter the material. Fight fire from maximum distance.
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]
(Non-Specific -- Carbamate Pesticide, Solid, n.o.s.) Keep unnecessary people away and stay upwind. Do not touch the material or handle broken packages without protective clothing. Use water spray to reduce vapors. Take up spills with non-combustible absorbent material. For small dry spills, place material in a clean dry container with a clean shovel and cover; remove from site of spill. For large spills dike far ahead for later disposal. (EPA, 1998)
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
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.
Avoid contact with mouth, skin, eyes. Keep out of reach of children. /2-(1-Methylethyl)phenyl methylcarbamate/
When a pesticide is of moderate or higher hazard & can be readily absorbed through skin, special precautions are necessary. In some situations where men may become accidentally contaminated with large quantities of concentrates, such as in factory situations & mixing, it is necessary to provide a shower bath in addition to usual washing facilities. Special arrangements for cleaning clothing & overalls may be necessary ... Smoking, eating & drinking before washing should be ... prohibited when any pesticide of moderate or higher toxicity is being handled or used. /Pesticides/
For more Preventive Measures (Complete) data for PHENOL,3(1-METHYLETHYL)-,METHYLCARBAMATE (6 total), please visit the HSDB record page.
0.048 [mg/m3]
0.53 [mg/m3]
3.2 [mg/m3]
For emergency situations, wear a positive pressure, pressure-demand, full facepiece self-contained breathing apparatus (SCBA) or pressure- demand supplied air respirator with escape SCBA and a fully-encapsulating, chemical resistant suit. (EPA, 1998)
Goggles, rubber gloves, ... /NIOSH approved breathing apparatus/ or respirator, rubber boots, long-sleeved shirt/jacket, long pants. /2-(1-Methylethyl)phenyl methylcarbamate/
If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally.
The effects of eserine /(physostigmine)/, and carbaryl (l-naphthyl-N-methyl carbamate) on discrete avoidance behavior and brain cholinesterase inhibition were studied in rats. The influence of SKF525-A (-diethylaminoethyl diphenylpropylacetate HCl) on the effects of these agents was investigated. When given alone at a dose of 25 mg/kg, SKF525-A did not alter behavioral response or brain cholinesterase levels. When it was given 30 min prior to eserine, a 4- to 8-fold increase in the number of shocks normally taken after eserine alone was observed with a similar enhancement of inhibitory effects of cholinesterase. Similar schedules with /(Phenol, 3-(1-methylethyl)-methylcarbamate)/ or carbaryl revealed about a 2-fold enhancement of the behavioral effects of these agents. Concomitant potentiation of anticholinesterase effects was obtained with /(Phenol, 3-(1-methylethyl)-methylcarbamate)/ but not with carbaryl.
... Animals were given from 1 to 100 milligrams per kilograms of Zectran (315184), o-isopropoxyphenyl-methylcarbamate, m-isopropylphenyl-methylcarbamate, /(Phenol, 3-(1-methylethyl)-methylcarbamate)/ 2,3-dihydro-2-methylfuran-7-yl-methylcarbamate, 2-methyl-2-methyl-thiopropionaldehyde-O-(methylcarbamoyl)-oxime, ethyl-3-hydroxy-2-methylacrylate-diethyl-phosphate, and O,O-diethyl-S-(methylcarbamoylethyl)-phosphorodithioate by stomach intubation. Therapeutic doses of atropine or TEAB were given at the same time or 5 to 10 minutes after the insecticide. ... The onset of signs of poisoning after dosing with carbamates was very rapid. Both atropine and TEAB were effective in controlling the effects of the carbamates. Atropine tended to control symptoms and produce recovery faster than TEAB. TEAB was as effective as atropine against 2,3-dihydro-2-methylfuran-7-yl-methylcarbamate only. Atropine was greatly superior to TEAB as a therapeutic agent following dosing with organophosphorus compounds. TEAB had little or no effect.
Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Chronically high (>10 years) exposure leads to neuropsychological consequences including disturbances in perception and visuo-motor processing (A15321).
LC50 Cyprinus carpio (carp) 4.2 mg/l/48 hr /Conditions of bioassay not given/
EC50 Daphnia magna (Water flea; intoxication, immobilization) 5 ug/L/30 min; static /formulated product/
LC50 Lepomis macrochirus (Bluegill) 82 ug/L/24 hr (95% confidence interval: 42-162 ug/L); static /formulated product/
LC50 Oncorhynchus mykiss (Rainbow trout) 270 ug/L/24 hr (95% confidence interval: 203-357 ug/L); static /formulated product/
LC50 Oncorhynchus mykiss (Rainbow trout) 140 ug/L/96 hr (95% confidence interval: 94-209 ug/L); static /formulated product/
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 640(SRC), determined from a log Kow of 2.63(2) and a regression-derived equation(3), indicates that 3-isopropylphenyl methyl carbamate is expected to have moderate mobility in soil(SRC). Volatilization of 3-isopropylphenyl methyl carbamate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 6.3X10-8 atm-cu m/mole(SRC), using a fragment constant estimation method(4). 3-Isopropylphenyl methyl carbamate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.0044 mm Hg(SRC), determined from a fragment constant method(5). While data specific to 3-isopropylphenyl methyl carbamate are lacking(SRC), numerous genera of carbamate-hydrolyzing bacteria have been identified, including Pseudomonas, Arthrobacter, Bacillus, Nocardia, Achromobacter, Flavobacterium, Streptomyces, Alcaligenes, Azospirillum, Micrococcus, and Rhodococcus(6).
Terrestrial fate: Moderately long residual activity. /2-(1-Methylethyl)phenyl methylcarbamate/
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 640 (SRC), determined from a log Kow of 2.63(2) and a regression-derived equation(3), indicates that 3-isopropylphenyl methyl carbamate 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 6.3X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 21(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). A base-catalyzed second-order hydrolysis rate constant of 3.0 L/mole-sec(SRC) was estimated using a structure estimation method(7); this corresponds to half-lives of 27 days and 2.7 days at pH values of 7 and 8, respectively(7). While data specific to 3-isopropylphenyl methyl carbamate are lacking(SRC), numerous genera of carbamate-hydrolyzing bacteria have been identified, including Pseudomonas, Arthrobacter, Bacillus, Nocardia, Achromobacter, Flavobacterium, Streptomyces, Alcaligenes, Azospirillum, Micrococcus, and Rhodococcus(8).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 3-isopropylphenyl methyl carbamate, which has an estimated vapor pressure of 0.0044 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor. Vapor-phase 3-isopropylphenyl methyl carbamate 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 12 hours(SRC), calculated from its rate constant of 11X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 3-Isopropylphenyl methyl carbamate does not contain chromophores that absorb at wavelengths >290 nm needed to make direct photolysis an important environmental degradation process(SRC).
m-Cumenyl methylcarbamate is a cholinesterase or acetylcholinesterase (AChE) inhibitor. Carbamates form unstable complexes with chlolinesterases by carbamoylation of the active sites of the enzymes. This inhibition is reversible. A cholinesterase inhibitor suppresses the action of acetylcholine esterase. Because of its essential function, chemicals that interfere with the action of acetylcholine esterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses. Headache, salivation, nausea, vomiting, abdominal pain and diarrhea are often prominent at higher levels of exposure. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop.
As with organophosphates, the signs and symptoms are based on excessive cholinergic stimulation. Unlike organophosphate poisoning, carbamate poisonings tend to be of shorter duration because the inhibition of nervous tissue acetylcholinesterase is reversible, and carbamates are more rapidly metabolized. Muscle weakness, dizziness, sweating and slight body discomfort are commonly reported early symptoms. Headache, salivation, nausea, vomiting, abdominal pain and diarrhea are often prominent at higher levels of exposure. Contraction of the pupils with blurred vision, incoordination, muscle twitching and slurred speech have been reported. (L795)
P202; As stipulated in 40 CFR 261.33, when m-cumenyl methylcarbamate, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to federal and/or state hazardous waste regulations. Also defined as a hazardous waste is any container or inner liner used to hold this waste or any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5(e)).
Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 1 lb. The toll free number of the NRC is (800) 424-8802; In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).
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. Phenol, 3-(1-methylethyl)-, methylcarbamate is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 500 or 10,000 lbs. Extremely hazardous substances that are solids are subject to either of two threshold planning quantities ... The lower quantity applies only if the solid exists in powdered form and has a particle size less than 100 microns; or is handled in solution or in molten form; or meets the criteria for a National Fire Protection Association (NFPA) rating of 2, 3 or 4 for reactivity. If the solid does not meet any of these criteria, it is subject to the upper ... threshold planning quantity ... .
Studies conducted with UC-10854 labeled (14)C-CH3 & (14)C-C=O showed that (14)C-carbon dioxide arose from both in treated houseflies. Houseflies also hydrolyzed this material to the corresponding phenol.
After treatment of bean plants with UC-10854, in addition to several unidentified compounds, the hydroxypropyl & N-hydroxymethyl analogs were found.
The meta-isomer of isoprocarb (m-isopropylphenyl N-methylcarbamate) is much more toxic to animals /than the ortho-isomer/ ... Perhaps its higher toxicity is due to its metabolism by side chain oxidation to yield (1-hydroxy-1-methylethyl)phenyl methylcarbamate, which is also a cholinesterase inhibitor.
For more Metabolism/Metabolites (Complete) data for PHENOL,3(1-METHYLETHYL)-,METHYLCARBAMATE (7 total), please visit the HSDB record page.
The carbamates are hydrolyzed enzymatically by the liver; degradation products are excreted by the kidneys and the liver. (L793)
Little information is available on the distribution of carbamates in the various organs and tissues in mammals following exposure by inhalation or the oral route. The organs in which residues have been reported are the liver, kidneys, brain, fat, and muscle. The half-life in the rat is of the order of 3-8 hr. It seems that the excretion of carbamates via urine is also rapid in man, and that the metabolic pathways in man are the same as those in the rat. /Carbamate pesticides/
In vivo studies have shown that carbamates are almost completely absorbed during normal transit through the gastrointestinal tract. ...In mice, all carbamates were rapidly distributed to the tissues and organs. The half-life values of penetration ranged from 8-17 min for carbamates. ...In animals, oxidation of carbamates often, but not always, results in detoxification. Oxidative metabolism generally leads to products of greater polarity and water solubility, and these can be more readily eliminated through the urine and feces than the parent compound. /Carbamate pesticides/
Used as insecticide for cotton, fruits, vegetables, and field crops; [CAMEO]
No longer registered as a pesticide for use in the US; [HSDB]
Farming (Pesticides) [Category: Industry]
For phenol, 3-(1-methylethyl)-, methylcarbamate (USEPA/OPP Pesticide Code: 047801) 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./
m-Cumenyl methylcarbamate is widely used as an insecticide or pesticide in homes, gardens and agricultural applications. It is a synthetic compound.
It was available as a 50% wettable powder & a 14% emulsifiable concentrate.
Dust - 2% active ingredient. Granule - 4% active ingredient. Thermal fog 15%. Emulsifiable concentrate - 20% active ingredient. Wettable powder - 50% active ingredient. gamma-Mipcin - contains 4% MIPC /2-(1-methylethyl)phenyl methylcarbamate/ & 5% /gamma-benzene hexachloride/ gamma-BHC. /2-(1-Methylethyl)phenyl methylcarbamate/
An insecticide introduced by Hercules Inc (now Nor-Am) and Union Carbide Corp ...
Discontinued by Rhone-Poulenc Ag Co
It is thought to be incompatible with alkali.
Recommended for use on paddy rice, primarily for control of plant & leaf hoppers at 0.5 to 1.0 kg ai/ha or 1.0 to 1.5 kg ai/ha for granular application to water surface. /2-(1-Methylethyl)phenyl methylcarbamate/
Verwenden3-Isopropylphenyl Methylcarbamate is a potential human-safe insecticide against the malaria mosquito.