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Home > Encyclopedia > m-Cumenyl methylcarbamate

m-Cumenyl methylcarbamate

m-Cumenyl methylcarbamate structure

m-Cumenyl methylcarbamate 

structure
  • CAS No:

    64-00-6

  • Formula:

    C11H15NO2

  • Chemical Name:

    m-Cumenyl methylcarbamate

  • Synonyms:

    Phenol,3-(1-methylethyl)-,1-(N-methylcarbamate);Carbamic acid,methyl-,m-cumenyl ester;Phenol,3-(1-methylethyl)-,methylcarbamate;OMS 162;AC 5727;H 5727;H 8757;UC 10854;ENT 25500;Compound 10854;m-Cumenol methylcarbamate;m-Cumenyl methylcarbamate;Hercules 5727;m-Isopropylphenyl methylcarbamate;3-Isopropylphenyl methylcarbamate;m-Isopropylphenyl N-methylcarbamate;3-Isopropylphenyl N-methylcarbamate;Hercules AC 5727;OMS 15;m-Isopropylphenol methylcarbamate;(3-Propan-2-ylphenyl) N-methylcarbamate

Description

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)


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)


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)

m-Cumenyl methylcarbamate Basic Attributes

193.24200

193.24

200-572-3

27502G8UZX

2757

DTXSID1040324

White crystalline solid

Characteristics

41.82000

2.73260

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)

1.039g/cm3

72-74 °C

260.9ºC at 760 mmHg

111.6ºC

1.507

85mg/L(30 ºC)

Store in a cool, dry place. /2-(1-methylethyl)phenyl methylcarbamate/

4.4X10-3 mm Hg at 25 deg C /Estimated/

LD50 oral in rat: 16mg/kg

Odorless

Henry's Law constant: 6.3X10-8 atm-cu m/mol at 25 °C /Estimated/

Technical grade isoprocarb is a colorless crystalline solid; insol in water, readily sol in acetone & methanol; mp: 88-93 °C; molecular wt: 193.2; molecular formula: C11H15NO2 /2-(1-Methylethyl)phenyl methylcarbamate/|Technical product white powder or flakes /2-(1-Methylethyl)phenyl methylcarbamate/|Log Kow= 2.80 /4-(1-Methylethyl)phenyl methylcarbamate/|Hydroxyl radical reaction rate constant: 1.08X10-11 cu cm/molec-sec at 25 °C /Estimated/

No rapid reaction with air. No rapid reaction with water.

Carbamates

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.

Safety Information

I

6.1(a)

UN 2757

This cmpd is stable to heat, light, & hydrolysis under normal conditions.

P262, P264, P270, P280, P301+P310, P302+P350, P310, P321, P322, P330, P361, P363, P405, P501

H301

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.

(Non-Specific -- Carbamate Pesticide, Solid, n.o.s.) Container may explode in heat of fire. When heated to decomposition, it emits toxic fumes of nitrogen oxides. Incompatible with alkalis. Avoid decomposing heat. (EPA, 1998)

|Danger|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|P262, P264, P270, P280, P301+P310, P302+P350, P310, P321, P322, P330, P361, P363, P405, and P501|Aggregated GHS information provided by 3 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

(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. (Non-Specific -- Carbamate Pesticide, Solid, n.o.s.) Extinguish with dry chemical, carbon dioxide, water spray, fog, or foam. (EPA, 1998)

Excerpt from ERG Guide 151 [Substances - Toxic (Non-combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

(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)

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/

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.

Carbamates produce slight to moderate skin and eye irritation, depending on the vehicle used, duration of contact, and on whether the substance is applied to the abraided or intact skin. From the available data, it cannot be excluded that some of the carbamates will have a slight to moderate sensitization potential. /Carbamate Pesticides/

P202; An acute hazardous waste when a discarded commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate.

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 ... .

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)).

Toxicity

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.

LD50 Rat male oral 31.0 mg/kg|LD50 Rat female oral 32.3 mg/kg|LD50 Rat male percutaneous 1500 mg/kg|LD50 Rat intramuscular 13.5 mg/kg|For more Non-Human Toxicity Values (Complete) data for PHENOL,3(1-METHYLETHYL)-,METHYLCARBAMATE (18 total), please visit the HSDB record page.

/OTHER TERRESTRIAL SPECIES/ Harmful to honey bees. /2-(1-Methylethyl)phenyl methylcarbamate/

3-Isopropylphenyl methyl carbamate's former(1) production and use as an insecticide(2) resulted in its direct release to the environment(SRC).

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).

The rate constant for the vapor-phase reaction of 3-isopropylphenyl methyl carbamate with photochemically-produced hydroxyl radicals has been estimated as 11X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 12 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). A base-catalyzed second-order hydrolysis rate constant of 3.0 L/mole-sec(SRC) was estimated using a structure estimation method(2); this corresponds to half-lives of 27 days and 2.7 days at pH values of 7 and 8, respectively(2). 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). No photodegradation was observed in a 1 mg/ml ethanol or hexane solution exposed 3 hours to summer sunlight(3).

An estimated BCF of 21 was calculated for 3-isopropylphenyl methyl carbamate(SRC), using a log Kow of 2.63(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC), provided the compound is not altered physically or chemically once released into the environment(SRP).

The Koc of 3-isopropylphenyl methyl carbamate is estimated as 640(SRC), using a log Kow of 2.63(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 3-isopropylphenyl methyl carbamate is expected to have moderate mobility in soil.

The Henry's Law constant for 3-isopropylphenyl methyl carbamate is estimated as 6.3X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 3-isopropylphenyl methyl carbamate is expected to be essentially nonvolatile. 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(3).

Occupational exposure and general population exposure should be low or non-existent since 3-isopropylphenyl methyl carbamate since it is no longer produced or used in the US (April, 2005). In the past, 3-isopropylphenyl methyl carbamate was applied directly to the environment as an insecticide and exposure to this compound was primarily by inhalation and dermal contact with this compound at workplaces where 3-isopropylphenyl methyl carbamate was produced or used. (SRC)

Drug Information

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/

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.|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.

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/

It is a cholinesterase inhibitor. (EPA, 1998)

Note: Phenol, 3-(1-methylethyl)-, methylcarbamate is a cholinesterase inhibitor. Signs and Symptoms of Phenol, 3-(1-methylethyl)-, methylcarbamate Exposure: Acute exposure to phenol, 3-(1-methylethyl)-, methylcarbamate usually leads to a cholinergic crisis. Signs and symptoms may include increased salivation, profuse sweating, lacrimation (tearing), spontaneous defecation, and spontaneous urination. Pinpoint pupils, blurred vision, headache, tremors, muscle twitching, slight paralysis, and loss of muscle coordination may occur. Malaise, mental confusion, convulsions, loss of consciousness, and coma may also be noted. Emergency Life-Support Procedures: Acute exposure to phenol, 3-(1-methylethyl)-, methylcarbamate may require decontamination and life support for the victims. Emergency personnel should wear protective clothing appropriate to the type and degree of contamination. Air-purifying or supplied air respiratory equipment should also be worn, as necessary. Rescue vehicles should carry supplies such as plastic sheeting and disposable plastic bags to assist in preventing spread of contamination. Inhalation Exposure: 1. Move victims to fresh air. Emergency personnel should avoid self-exposure to phenol, 3-(1-methylethyl)-, methylcarbamate. 2. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer oxygen or other respiratory support. 3. Obtain authorization and/or further instructions from the local hospital for administration of an antidote or performance of other invasive procedures. 4. Rush to a health care facility. Dermal/Eye Exposure: 1. Remove victims from exposure. Emergency personnel should avoid self-exposure to phenol, 3-(1-methylethyl)-, methylcarbamate. 2. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer oxygen or other respiratory support. 3. Remove and isolate contaminated clothing as soon as possible. 4. If eye exposure has occurred, eyes must be flushed with lukewarm water for at least 15 minutes. 5. Wash exposed skin areas thoroughly with water. 6. Obtain authorization and/or further instructions from the local hospital for administration of an antidote or performance of other invasive procedures. 7. Rush to a health care facility. Ingestion Exposure: 1. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer oxygen or other respiratory support. 2. Obtain authorization and/or further instructions from the local hospital for administration of an antidote or performance of other invasive procedures. 3. Vomiting may be induced with syrup of Ipecac. If elapsed time since ingestion of phenol, 3-(1-methylethyl)-, methylcarbamate is unknown or suspected to be greater than 30 minutes, do not induce vomiting and proceed to Step 4. Ipecac should not be administered to children under 6 months of age. Warning: Ingestion of phenol, 3-(1-methylethyl)-, methylcarbamate may result in sudden onset of seizures or loss of consciousness. Syrup of Ipecac should be administered only if victims are alert, have an active gag-reflex, and show no signs of impending seizure or coma. If ANY uncertainty exists, proceed to Step 6. The following dosages of Ipecac are recommended: children up to 1 year old, 10 mL (1/3 oz); children 1 to 12 years old, 15 mL (1/2 oz); adults, 30 mL (1 oz). Ambulate (walk) the victims and give large quantities of water. If vomiting has not occurred after 15 minutes, Ipecac may be readministered. Continue to ambulate and give water to the victims. If vomiting has not occurred within 15 minutes after second administration of Ipecac, administer activated charcoal. 4. Activated charcoal may be administered if victims are conscious and alert. Use 15 to 30 g (1/2 to 1 oz) for children, 50 to 100 g (1-3/4 to 3-1/2 oz) for adults, with 125 to 250 mL (1/2 to 1 cup) of water. 5. Promote excretion by administering a saline cathartic or sorbitol to conscious and alert victims. Children require 15 to 30 g (1/2 to 1 oz) of cathartic; 50 to 100 g (1-3/4 to 3-1/2 oz) is recommended for adults. 6. Rush to a health care facility. (EPA, 1998)

Maintain an open airway and assist ventilation if necessary. Pay careful attention to respiratory weakness; sudden respiratory arrest may occur. This is often preceded by increasing weakness of neck flexion muscles. If intubation is required, note the potential for interaction between neuromuscular blockers and cholinesterase inhibitors. Administer supplemental oxygen. Treat hydrocarbon pneumonitis, seizures, and coma if they occur. Observe asymptomatic patients for at least 8-12 hours to rule out delayed onset symptoms especially after extensive skin exposure or ingestion of a highly fat-soluble agent. Specific treatment includes the antimuscarinic agent atropine and the enzyme reactivator pralidoxime. ... Do not induce vomiting because of the risk of abrupt onset of toxicity. ... Administer activated charcoal (cathartics are not necessary if the patient already has diarrhea ). Consider inserting a small flexible gastric tube to aspirate liquid gastric contents, if this procedure can be carried out safely and within 1-2 hours of ingestion. The inadvertent introduction of hydrocarbon solvents into the lungs through overly aggressive gastric lavage may kill the patient.) /Organophosphorus and Carbamate insecticides/|Basic treatment: Establish a patent airway. Suction if necessary. Aggressive airway control may be needed. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Carbamates and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. For hypotension if signs of hypovolemia are present, administer fluid cautiously. Watch for signs of pulmonary edema ... . Administer atropine. Correct hypoxia before administration ... . In severely poisoned patients, administer pralidoxime chloride (2 PAM). DIRECT PHYSICIAN ORDERS ONLY ... . Treat seizures with adequate atropinization and correction of hypoxia. Rarely is diazepam necessary ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Carbamates and related compounds/|Elimination Enhancement: No methods are recommended, because of the short clinical effect of carbamates and the presence of an effective antidote (atropine). /Carbamates/|For more Antidote and Emergency Treatment (Complete) data for PHENOL,3(1-METHYLETHYL)-,METHYLCARBAMATE (17 total), please visit the HSDB record page.

/SIGNS AND SYMPTOMS/ Except for diminished intensity and duration, particularly of the central nervous signs and symptoms, carbamate poisoning resembles parathion intoxication in its clinical manifestations. 1. Nausea, vomiting, abdominal cramps, diarrhea and excessive salivation (sialorrhea) and sweating. 2. Lassitude and weakness. 3. Rhinorrhea and a sensation of tightness in the chest may occur with respiratory exposures. 4. Blurring or dimness of vision, miosis (with fixed pinpoint pupils), tearing, ciliary muscle spasm, loss of accommodation and ocular pain. None of these eye signs, however, is dependable for diagnosis. Mydriasis may be seen secondary to sympathoadrenal discharge. 5. Loss of muscle coordination, slurring of speech, fasciculations and twitching of muscles. 6. Difficulty in breathing, excessive secretions of saliva and of respiratory tract mucus, oronasal frothing, cyanosis, pulmonary rales and rhonchi and hypertension (presumably due to asphyxia). 7. Random jerky movements, incontinence, convulsions and coma. 8. Death primarily due to respiratory arrest of central origin, paralysis of the respiratory muscles, intense bronchoconstriction or all three.|/SIGNS AND SYMPTOMS/ The clinical picture of carbamates intoxication results from accumulation of ACh at nerve endings. ...The signs and symptoms can be categorized into the following 3 groups: (a) Muscarinic manifestations - increased bronchial secretion, excessive sweating, salivation, and lachrymation; pinpoint pupils, bronchoconstriction, abdominal cramps (vomiting and diarrhea); and bradycardia. (b) Nicotinic manifestations - fasciculation of fine muscles (in severe cases, diaphragm and respiratory muscles also involved); and tachycardia. (c) Central nervous system manifestations- headache, dizziness, anxiety, mental confusion, convulsions, and coma; and depression of respiratory center. All these signs and symptoms can occur in different combinations and can vary in onset and sequence, depending on the chemical, dose, and route of exposure. The duration of symptoms is usually shorter than that observed in organophosphorus poisoning. Mild poisoning might include muscarinic and nicotinic signs only. Severe cases always show central nervous system involvement; the clinical picture is dominated by the respiratory failure sometimes leading to pulmonary edema due to the combination of the above mentioned symptoms. /Carbamate pesticides/|/CASE REPORTS/ 3-Isopropylphenyl-N-methylcarbamate was tested in a nearby village by the WHO Insecticide Testing Unit at Lagos. Water-wettable powder was applied at a final concentration of 5% active ingredient to leave a deposit of 2 g/sq m. The 8 spraymen and 2 supervisors wore mask, overalls, oilskin caps (Southwesters), and gumboots. ...All spraymen became ill within 2-3 hr, and work was stopped. Weakness, dizziness, tightness in chest, headache, pinpoint pupils and profuse sweating were the most common symptoms and signs observed. ...During the afternoon following spraying, 3 of the 70 villagers developed giddiness, 5 vomited and a 14-month-old child who was severely poisoned was taken from the village to Lagos during the night. On arrival, the child was semiconscious groaning, and breathing rapidly. Pulse rate was 200, the pupils were pinpoint, and sweating was profuse. Within 1 hr after im injection of 0.5 mg of atropine sulfate, sweating had stopped and lungs were clearing. By morning, the child was able to smile and play. Back at the village, 2 persons were still vomiting; they were relieved within 30 min by atropine. In addition to signs of poisoning by cholinergic agent, 17 of 34 males and 1 of 36 female inhabitants... developed skin eruptions...

m-Cumenyl methylcarbamate Use and Manufacturing

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/

... 52 pesticides including 3-isopropyl phenyl N-methylcarbamate /were surveyed/ by phosphorimetric measurement including their limits of detection & spectral characteristics. It was feasible to detect the carbamates at concn of 5-10 ng/ml.|Product analysis is by uv spectroscopy; details of methods are available from Bayer AG. Residues may be determined by glc (Nihon Noyaku Gakkaishi, 1978, 3, 119). /2-(1-Methylethyl)phenyl methylcarbamate/

INSECTICIDES

Computed Properties

Molecular Weight:193.24
XLogP3:2.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:193.110278721
Monoisotopic Mass:193.110278721
Topological Polar Surface Area:38.3
Heavy Atom Count:14
Complexity:192
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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