2,3,5-Trimethacarb
-
2,3,5-Trimethacarb
structure -
-
CAS No:
2655-15-4
-
Formula:
C11H15NO2
-
Chemical Name:
2,3,5-Trimethacarb
-
Synonyms:
Phenol,2,3,5-trimethyl-,1-(N-methylcarbamate);Carbamic acid,methyl-,2,3,5-trimethylphenyl ester;Phenol,2,3,5-trimethyl-,methylcarbamate;2,3,5-Trimethylphenyl methylcarbamate;SD 8786;2,3,5-Landrin;Landrin B;2,3,5-Trimethacarb;2,3,5-Trimethylphenyl N-methylcarbamate
- Categories:
-
CAS No:
Description
ChEBI: A carbamate ester that consists of 2,3,5-trimethylphenol carrying an O-(N-methylcarbamoyl) group. One of two constituents of trimethacarb.
2,3,5-trimethylphenyl methylcarbamate is a brown crystalline solid. Non corrosive. Used as an insecticide.
2,3,5-trimethylphenyl methylcarbamate is a brown crystalline solid. Non corrosive. Used as an insecticide.|2,3,5-trimethylphenyl methylcarbamate is a carbamate ester that consists of 2,3,5-trimethylphenol carrying an O-(N-methylcarbamoyl) group. One of two constituents of trimethacarb. It has a role as an agrochemical and an insecticide. It derives from a 2,3,5-trimethylphenol.
Characteristics
38.3
2.55
2,3,5-trimethylphenyl methylcarbamate is a brown crystalline solid. Non corrosive. Used as an insecticide.
1.0±0.1 g/cm3
123-124 °C @ Solvent: Methanol, Ethanol, Octane
287.8±40.0 °C at 760 mmHg
>100 °C
1.515
0-6°C
Brown crystalline solid; MP: 105-114 °C; not readily soluble in organic solvents; sol in water, 58 mg/l @ 23 °C; VP: 5.1X10-5 mm Hg @ 25 °C. Decomposed by strong acids and alkalis; stable to light. /Trimethacarb/
Hydrolyzed in strong acid or alkaline media.
Carbamates
2,3,5-TRIMETHYLPHENYL 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
UN28116.1/PG3
22-36
26
FC8405000
Xn
Stable to light.
P264, P270, P280, P301+P310, P305+P351+P338, P321, P330, P337+P313, P405, P501
H301
Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Some are oxidizers and may ignite combustibles (wood, paper, oil, clothing, etc.). Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. For electric vehicles or equipment, ERG Guide 147 (lithium ion batteries) or ERG Guide 138 (sodium batteries) should also be consulted. (ERG, 2016)
|Danger|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|P264, P270, P280, P301+P310, P305+P351+P338, P321, P330, P337+P313, P405, and P501|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: SMALL FIRE: Dry chemical, CO2 or water spray. LARGE FIRE: Dry chemical, CO2, alcohol-resistant foam or water spray. Move containers from fire area if you can do it without risk. Dike fire-control water for later disposal; do not scatter the material. FIRE INVOLVING TANKS OR CAR/TRAILER LOADS: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. Do not get water inside containers. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. (ERG, 2016)
Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (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)
Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. (ERG, 2016)
Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. (ERG, 2016)
Toxicity
LD50 Rat oral 125-232 mg/kg /from table/|LD50 Dog (male) oral 225 mg/kg /from table/|LD50 Rabbit dermal >2000 - >2500 mg/kg /from table/|LD50 Rat percutaneous >2000 mg/kg
2,3,5-Trimethacarb's production may result in its release to the environment through various waste streams; it's use as an ingredient in the insecticide trimethacarb(1) will result in its direct release to the environment(SRC). The insecticide trimethacarb is a reaction product consisting of 3,4,5-trimethylphenyl methylcarbamate and 2,3,5-trimethylphenyl methylcarbamate in a ratio between 3.5:1 and 5:1(1).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 470(SRC), determined from a measured water solubility of 58 mg/l(2) and a regression-derived equation(3), indicates that 2,3,5-trimethacarb is expected to have moderate mobility in soil(SRC). Volatilization of 2,3,5-trimethacarb from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.2X10-7 atm-cu m/mole(SRC), calculated from trimethacarb's vapor pressure, 5.1X10-5 mm Hg(2), and water solubility, 58 mg/l(2). 2,3,5-Trimethacarb is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(2). The half-life of trimethacarb in a sterile soil was 60 days(2), which suggests hydrolysis is expected to be an important fate process for 2,3,5-trimethacarb. The half-life of 2,3,5-trimethacarb in an aerated, dry, Drummer-Catlin soil mixture was 42 days(4), which suggests biodegradation will be important in soils.|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 470(SRC), determined from a measured water solubility of 58 mg/l(2)and a regression-derived equation(3), indicates that 2,3,5-trimethacarb 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 2.2X10-7 atm-cu m/mole(SRC), based upon trimethacarb's vapor pressure, 5.1X10-5 mm Hg(2), and water solubility, 58 mg/l(2). According to a classification scheme(4), an estimated BCF of 60(SRC), from its water solubility and a regression derived equation(3), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Hydrolysis is expected to be an important environmental fate process for 2,3,5-trimethacarb based upon estimated hydrolysis half-lives of 4 and 37 days at pH values of 7 and 8, respectively(5). No biodegradation data is available for 2,3,5-trimethacarb in water, however a half-life of about 42 days in a pristine-soil indicates that 2,3,5-trimethacarb will be moderately biodegradeable in water(6).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), trimethacarb, which has a vapor pressure of 5.1X10-5 mm Hg at 25 °C(2), is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase 2,3,5-trimethacarb 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 18 hours(SRC), calculated from its rate constant of 2.1X10-11 cu cm/molecule-sec at 25 °C (SRC) determined using a structure estimation method(3). Particulate-phase 2,3,5-trimethacarb may be removed from the air by wet and dry deposition(SRC).
The rate constant for the vapor-phase reaction of 2,3,5-trimethacarb with photochemically-produced hydroxyl radicals has been estimated as 2.1X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 18 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). A base-catalyzed second-order hydrolysis rate constant of 2.2 L/mole-sec(SRC) was estimated using a structure estimation method(2); this corresponds to half-lives of 4 and 37 days at pH values of 7 and 8, respectively(2). 2,3,5-Trimethacarb absorbs light weakly in the environmental UV spectrum and is stable to light(3).
An estimated BCF of 60 was calculated for 2,3,5-trimethacarb(SRC), using a water solubility of 58 mg/l(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC).
The Koc of 2,3,5-trimethacarb is estimated as 470(SRC), using a measured water solubility of 58 mg/l(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 2,3,5-trimethacarb is expected to have moderate mobility in soil(SRC).
The Henry's Law constant for 2,3,5-trimethacarb is estimated as 2.2X10-7 atm-cu m/mole(SRC) based upon trimethacarb's vapor pressure, 5.1X10-5 mm Hg(1), and water solubility, 58 mg/l(1). This Henry's Law constant indicates that 2,3,5-trimethacarb is not expected to volatilize from water surfaces(2). 2,3,5-Trimethacarb's estimated Henry's Law constant(1,2) indicates that volatilization from moist soil surfaces is not expected to be an important fate process(SRC). 2,3,5-Trimethacarb is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).
Occupational exposure to 2,3,5-trimethacarb may occur through inhalation and dermal contact with this compound at workplaces where trimethacarb is produced or used. (SRC)
Drug Information
In mice given C14 labeled preparations of trimethylphenyl methylcarbamates by gavage, each isomer formed 15-20 metabolites. Hydrolytic & nonhydrolytic metabolic routes were about equally important. With carbonyl-labeled isomers, urinary metabolites included glucuronide or sulfate conjugates; 17-35% of the radioactivity was expired as /carbon dioxide/ & 42-45% was excreted in the urine within 48 hr of admin.
In plants, metabolism occurs via hydroxylation of the N-methyl group & at the 3- & 4-methyl positions. All metabolites may be conjugated as glucosides.
Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. (ERG, 2016)
Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. For minor skin contact, avoid spreading material on unaffected skin. Keep victim calm and warm. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. (ERG, 2016)
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/
Two trials for malaria control carried out in Nigeria with Landrin lasted for 2 & 4 days, respectively. there were no complaints among the operators & residents, although in one of the trials a water shortage prevented operators form washing & bathing after work as frequently as planned. Whereas moderate to pronounced inhibition of whole-blood cholinesterase was observed in some sprayers at the end of the day's work, this was considerably less than that observed in the same sprayers when spraying propoxur at other times.
Landrin
2,3,5-Trimethacarb Use and Manufacturing
USEPA/OPP Pesticide Code 102402; Trade Names: Landrin (Part), SD 8530, Component of (with 102401), SD 8786.|Trimethacarb is a reaction product consisting of 3,4,5-trimethacarb and 2,3,5-trimethacarb in a ration between 3.5:1 and 5:1. /Trimethacarb/
FDA Method 231.1. Organophosphorous Residues General Methods for Fatty Foods Including Extraction of Fat, Acetonitrile Partition, and Florisil Column Cleanup. Detection limit not specified.|FDA Method 242.2. Method for N-Methylcarbamate Residues. Detection limit not specified.|FDA Method 252. Alternate Florisil Elution System. Detection limit not specified.
INSECTICIDES
Computed Properties
Molecular Weight:193.24
XLogP3:2.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:193.110278721
Monoisotopic Mass:193.110278721
Topological Polar Surface Area:38.3
Heavy Atom Count:14
Complexity:206
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Latest News on 2,3,5-Trimethacarb
- The project with an investment of ¥105 million and an annual output of 4000 tons of Propargite is to be built
- Nichino Mexico promotes a new Tolfenpyrad insecticide in Mexico
- Agri Technology Asia(2024) will be held in Lahore from July 27-29
- Bayer: Revenue of 13.765 billion euros( Q1)was in line with expectations
- IHARA plans to launch seven new solutions in Brazil by 2024
Learn More Other Chemicals
-
Deltamethrin
52918-63-5
-
Cypermethrin
86753-92-6
-
Chlorindan
57-74-9
-
S-Bioallethrin Formula
28434-00-6
-
Fenothiocarb1 Formula
62850-32-2
-
Dicyclanil Formula
112636-83-6
-
1,3-Difluoro-2-propanol Structure
453-13-4
-
Naled Structure
300-76-5
-
What is N,N-Diethyl-m-toluamide
134-62-3
-
What is Oxamyl
23135-22-0