Promecarb
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Promecarb
structure -
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CAS No:
2631-37-0
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Formula:
C12H17NO2
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Chemical Name:
Promecarb
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Synonyms:
Phenol,3-methyl-5-(1-methylethyl)-,1-(N-methylcarbamate);Carbamic acid,methyl-,m-cym-5-yl ester;Phenol,3-methyl-5-(1-methylethyl)-,methylcarbamate;EP 316;Schering 34615;m-Cym-5-yl methylcarbamate;Minacide;Morton EP-316;ITC;Sch 34615;3-Methyl-5-isopropylphenyl methylcarbamate;Promecarb;Carbamult;3-Methyl-5-isopropylphenyl N-methylcarbamate;3-Isopropyl-5-methylphenyl N-methylcarbamate;3-Isopropyl-5-methylphenyl methylcarbamate;NSC 35378;3-Methyl-5-i-propylphenyl N-methylcarbamate;4111-89-1;31677-56-2
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CAS No:
Description
Colorless, crystalline solid. Insoluble in water; soluble in alcohol. Promecarb is a colorless, odorless, crystalline solid
Almost odorless, colorless crystalline solid. Used as a non-systemic contact insecticide. Not for sale or use in the USA. (EPA, 1998)
Almost odorless, colorless crystalline solid. Used as a non-systemic contact insecticide. Not for sale or use in the USA. (EPA, 1998)|Promecarb is an alkylbenzene.
Promecarb Basic Attributes
207.27
207.27
220-113-0
1QRP20775S
35378
2757
DTXSID4037617
COLORLESS CRYSTALLINE SOLID
2924199090
Characteristics
38.33000
2.96
Crystalline
1.0±0.1 g/cm3
87-87.5 °C
117 °C @ Press: 0.1 Torr
124.3±27.3 °C
1.507
92mg/L(room temperature)
0-6°C
3X10-5 mm Hg @ 25 deg C
Oral-Rat LD50: 35 mg/kg; Oral-Mouse LD50: 16 mg/kg
Combustion produces toxic nitrogen oxide gas
ALMOST ODORLESS
150.39 Ų [M+H]+
Hydrolyzed by strong acids and alkalis|Henry's Law Constant= 9.0X10-8 atm-cu m/mole (est).
No rapid reaction with air. No rapid reaction with water.
Carbamates
PROMECARB 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.
Non-corrosive
Safety Information
II
6.1(a)
2757
3
25-50/53
24-37-45-60-61
FB8050000
T,N
The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials
Hydrolyzed in alkalies
Missing Phrase - N15.00950417-P280-P302 + P352 + P312
H300-H311-H410
Hydrolysis: Promecarb should be treated with alkali and then buried. Recommendable methods: Incineration & landfill.
(Non-Specific -- Carbamate Pesticide, Solid, n.o.s.) Container may explode in heat of fire. Fire and runoff from fire control water may produce irritating or poisonous gases. Hydrolyzed by alkalis. Stable. No changes observed on storage for 140 hours at122F. (EPA, 1998)
|Danger|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P264, P270, P273, P301+P310, P321, P330, P391, P405, and P501|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|Aggregated GHS information provided by 197 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H300: Fatal if swallowed [Danger Acute toxicity, oral]|P260, P264, P270, P280, P301+P310, P302+P352, P309+P311, P312, P314, P321, P322, P330, P361, P363, P405, and P501
(Non-Specific -- Carbamate Pesticide, Solid, n.o.s.) Stay upwind; keep out of low areas. 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. (Non-Specific -- Carbamates) Extinguish fire using agent suitable for the surrounding fire, as the material itself burns with difficulty. Use water in flooding quantities as a fog. Use alcohol foam, carbon dioxide, or dry chemical. (Non-Specific -- Carbamate Pesticide, Solid, n.o.s.) This material may burn, but does not ignite readily. For small fires, use dry chemical, carbon dioxide, water spray, or foam. For large fires, use 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; isolate hazard areas and deny entry. Stay upwind and keep out of low areas. Do not touch spilled material or breathe the dusts, vapors, or fumes from burning materials. Use water spray to reduce vapors. Do not handle broken packages without protective equipment. Wash away any material that may have contacted the body with soap and water. Take up small spills with sand or other noncombustible absorbent material and place in containers for later disposal. Small dry spills: with clean shovel place material into clean, dry container and cover; move containers from spill area. Dike far ahead of large spills 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)|Wear protective clothing when working with undiluted preparation.
Carefully wash with soap & water any parts or the skin contracted with promecarb.
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
most toxic
LD50 Rat percutaneous > 1000 mg active ingredient (as 50% wp)/kg|LD50 Rabbit percutaneous > 1000 mg active ingredient (as 50% wp)/kg|LD50 Rat dermal 688 mg/kg|LD50 Mouse oral 39.5 mg/kg|For more Non-Human Toxicity Values (Complete) data for PROMECARB (7 total), please visit the HSDB record page.
Promecarb is used as a non-systemic contact insecticide against lepidopterous pests and leaf miners of fruits(1). Insecticidal applications of promecarb release the compound directly into the environment(SRC).
TERRESTRIAL FATE: The N-methylcarbamate pesticides (of which promecarb is a member) are generally biodegradable and of low soil persistence(1). Chemical degradation of promecarb in moist soil is expected to proceed via hydrolysis. The aqueous hydrolysis half-life has been estimated to be 1.2 days at 25 °C and pH 7; the hydrolysis rate is expected to increase under alkaline conditions, but decrease with acidity in soil. Promecarb is expected to have low to moderate soil mobility which suggests that some leaching may be possible. Leaching in neutral and alkaline soils may not be significant, however, due to concurrent hydrolysis(SRC).|AQUATIC FATE: Hydrolysis appears to be an important degradation process for promecarb in water. The aqueous hydrolysis half-life has been estimated to be 1.2 days at 25 °C and pH 7(1); the hydrolysis rate is expected to increase under alkaline conditions, but may decrease significantly in acidic in natural waters.|ATMOSPHERIC FATE: Based upon a vapor pressure of 0.00003 mm Hg at 25 °C(1), promecarb can be expected to exist in both the gas phase and particulate phase in the ambient atmosphere(2,SRC). Gas phase promecarb is expected to degrade rapidly in air by reaction with photochemically produced hydroxyl radicals; the half-life for this reaction in an average atmosphere has been estimated to be about 5 hr. Particulate phase promecarb may be physically removed from air via wet and dry deposition(SRC).
The rate constant for the vapor phase reaction of promecarb with photochemically produced hydroxyl radicals has been estimated to be 77X10-12 cu cm/molecule-sec at 25 °C which corresponds to an atmospheric half-life of about 5 hr at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1,SRC). Promecarb is hydrolyzed by strong acids and bases and is incompatible with alkaline preparations(2). The aqueous hydrolysis half-life of promecarb at 25 °C and pH 7 has been estimated to be 1.2 days(3). At 22 °C, promecarb is reported to be stable at pH 5, but 50% loss occurs in 5.2 days at pH 7 and 50% loss occurs in 1.5 days at pH 9(4).
Based upon a water solubility of 91 ppm at 25 °C(1) and a measured log Kow of 3.10(2), the bioconcentration factor (BCF) for promecarb can be estimated to be 49 and 134, respectively, from recommended regression- derived equations(3,SRC). These BCF estimates suggest a low potential for bioconcentration(SRC).
302.00 L/kg|Utilizing soil thin-layer chromatography, the Rf value of promecarb in Hagerstown silty clay loam soil was measured to be 0.34 which is suggestive of low to moderate soil mobility(1). Based upon a water solubility of 91 ppm at 25 °C(2) and a measured log Kow of 3.10(3), the Koc value for promecarb can be estimated to range from 365 to 1240 from various regression-derived equations(4,SRC). These estimated Koc values also indicate low to medium soil mobility(5).
Based upon water solubility of 91 ppm and a vapor pressure of 0.00003 mm Hg at 25 °C(1), the Henry's Law Constant for promecarb can be estimated to be 9.0X10-8 atm-cu m/mole(SRC). This value of Henry's Law Constant indicates that volatilization from water is not significant(2).
Analysis by the US Food and Drug Administration of 7,893 samples of domestic and imported fruits and 165 ready to eat fruit composites of the Total Diet Study for fiscal years 1970-1976 found promecarb in only one large fruit sample(1).
Occupational exposure to promecarb may be possible through dermal contact and inhalation to workers involved with applying or formulating promecarb pesticides. Exposure may be possible through consumption of fruit products treated with promecarb pesticides. (SRC)
Drug Information
... /CARBAMATE INSECTICIDES/ ARE RAPIDLY METABOLIZED, 80% OF DOSE BEING ELIMINATED IN URINE, MAINLY AS SULFATE OR GLUCURONIDE CONJUGATE, WITHIN 24 HR; 0.5 TO 1.5% IS FOUND IN FECES, 0.1 TO 1.0% IN THE MILK. /CARBAMATES/|In order to learn why cholinesterase remains inhibited longer in workers exposedto promecarb than in those exposed to propoxur, dogs were injected im or iv with approximately equitoxic doses of the compounds. It required 3 full days for cholinesterase activity to return to normal in a dog that received promecarb intramuscularly at a rate of 60 mg/kg, but recovery of cholinesterase activity was rapid after doses of propoxur sufficient to cause convulsions and marked ataxia. However, inhibition of cholinesterase activity was transient following intravenous administration of promecarb. It was concluded that prolonged inhibition of cholinesterase activity in days following im injection was the result of slow, continuing absorption and that, by extension, prolonged inhibition in workers has the same cause.|Penetration of the blood-brain barrier by the carbamates is insignificant; for this reason, fewer CNS symptoms occur. /Carbamate pesticides/
Promecarb was rapidly metabolized and eliminated when administered orally to rats. By 96 hours after administration, over 90% had been recovered from the urine and feces, mainly the former. Promecarb equivalent radioactivity in the tissues did not exceed 0.02 ppm.|(5-(14)C)Promecarb was administered orally to male Sprague Dawley rats. Within 4 days, about 88% of the dose was eliminated in the urine. In addition to isothymol, there were unidentified metabolites. Hydrolysis with glucuronidase indicated the conjugation of isothymol with glucuronic acid. Other conjugates present were not identified.|Promecarb was applied to soil and then corn seedlings were planted. Analyses of stem and leaves of the plants indicated the presence of isothymol and four unidentified metabolites as early as 15 days after application.|Spontaneous hydrolysis of the carbamate-cholinesterase complex occurs in vivo, leading to the disappearance of clinical effects within 24 hr. /Carbamate pesticides/
Carbamylation of acetylcholinesterase produces accumulation of acetylcholine and the picture of muscarine and nicotinic poisoning. /Carbamate pesticides/|Cholinesterase inhibitor.
Promecarb is highly toxic by ingestion and is absorbed through the intact skin. It is a reversible cholinesterase inhibitor and its effects are related to action on the nervous sysem. (EPA, 1998)
Note: Promecarb is a cholinesterase inhibitor. Signs and Symptoms of Promecarb Exposure: Acute exposure to promecarb 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, unconsciousness, and coma may also be noted. Gastrointestinal effects include nausea, vomiting, diarrhea, and abdominal pain. Bradycardia (slow heart rate) occurs frequently. Pulmonary edema, dyspnea (shortness of breath), labored breathing, respiratory depression, or respiratory arrest may also occur. Emergency Life-Support Procedures: Acute exposure to promecarb 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 promecarb. 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 promecarb. 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 promecarb 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 promecarb 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 4. 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)
Symptomatology: 1. Nausea, vomiting, abdominal cramps, diarrhea & excessive salivation ... sweating. 2. Lassitude & weakness. 3. Rhinorrhea and sensation of tightness in chest may occur with inhalation exposure. 4. Blurring or dimness of vision. Miosis ... tearing, ciliary muscle spasm, loss of accommodation and ocular pain. None of these ... signs ... is dependable for diagnosis. Mydriasis may be seen ... . 5. Loss of muscle coordination, slurring of speech, fasciculation & twitching of muscles. 6. Difficulty in breathing, excessive secretions of saliva and of resp tract mucus, oronasal frothing, cyanosis, pulmonary rales & rhonchi, and hypertension. 7. ... Jerky movements, incontinence, convulsions and coma. 8. Death ... due to resp arrest of central origin, paralysis of resp muscles, intense bronchoconstriction or all three. /Carbaryl/|... MOST OF AROMATIC CARBAMATE ESTER INSECTICIDES HAVE LOW DERMAL TOXICITIES. /CARBAMATES/|Promecarb was tried on a village scale at the WHO Insecticide Testing Unit in Nigeria, in 1965. Its residual action against adult mosquitos was found very effective. Three spraymen spent 3 days spraying empty houses and then 3 more days spraying an inhabited village. They were under constant medical supervision. There were no complaints, and clinical examination failed to reveal any signs. All the 90 inhabitants of the sprayed village were examined clinically at least once within the fortnight after spraying. The only findings were discrete skin eruptions in two young men. These eruptions, of an obvious contact dermatitis type, caused moderate itching that was relieved by calamine lotion; they disappeared completely in 5 to 6 days. ... The plasma cholinesterase levels were studied among the spraymen and residents by the electrometric, spectrophotometric, and Acholest methods; a significant depression of activity was demonstrated by all three. The plasma cholinesterase activity of the three spraymen was measured daily. All showed depressions from the first day onward. During 3 days of consecutive spraying, the level of activity went steadily down in two of the three spraymen. On the last day of the operation, the plasma cholinesterase activity of one sprayman was about 40.% of its original level when measured by the spectrophotometric and Acholest methods. Three to four days after the end of exposure, plasma cholinesterase activity among the spraymen had not quite returned to the level measured before exposure, but it was normal in 5 days. Among the residents, there was a decrease of plasma cholinesterase activity to about 50% of the prespraying level a week after the end of the spraying operations One month later, there was a general rise, but the plasma cholinesterase levels were still far below the original values.|When tested for malaria control, promecarb caused cholinesterase inhibition amoung both sprayers and villagers but no signs or symptoms in either except for contact dermatitis in two male villagers.
3-cym-5-yl methylcarbamate
Promecarb Use and Manufacturing
REACTION OF 3-ISOPROPYL-5-METHYLPHENOL & METHYL ISOCYANATE|/PROMECARB IS/ MADE BY REACTION OF 5-ISOPROPYL-M-CRESOL WITH METHYL ISOCYANATE ... .
Insecticide.
EMULSIFIABLE CONCENTRATE (200 G ACTIVE INGREDIENT/L); WETTABLE POWDER (375 AND 500 G/KG).
The WHO Recommended Classification of Pesticides by Hazard identifies Promecarb (technical grade) as an active ingredient believed to be obsolete or discontinued for use as a pesticide.|WEST GERMAN PATENT 1,156,272; BRITISH PATENT 916,707|PROMECARB IS A NON-SYSTEMIC CONTACT INSECTICIDE EFFECTIVE AGAINST COLEOPTEROUS PESTS SUCH AS POST-EMBRYONIC STAGES OF LEPTINOTARSA DECEMLINEATA @ 450 G ACTIVE INGREDIENT/HECTARE, AGAINST LEPIDOPTEROUS PESTS AND LEAF MINERS OF FRUIT @ 50-100 G/L.|INCOMPATIBLE WITH ALKALINE PREPARATIONS.
PRODUCT ANALYSIS IS BY HYDROLYSIS, ISOLATION OF METHYLAMINE WHICH IS ESTIMATED BY TITRATION. RESIDUES MAY BE DETERMINED BY GLC OR BY MEASUREMENT OF 5-METHYL-M-CUMENOL PRODUCED ON HYDROLYSIS.|Several procedures for the direct conversion of carbamates to cmpd amenable to GC analysis were studied for possible application to a wide range of carbamate pesticide residues. Pentafluorobenzyl bromide was used as a derivatization reagent with 23 carbamates of widely defferent structures. The carbamates studied included promecarb.|Analysis of product is by acidimetric titration or by TLC /potentiometric titration. Residue analysis is by HPLC with electrochemical detection or by GLC.
Agrochemicals -> Insecticides
Computed Properties
Molecular Weight:207.27
XLogP3:3.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:207.125928785
Monoisotopic Mass:207.125928785
Topological Polar Surface Area:38.3
Heavy Atom Count:15
Complexity:216
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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