Thiodicarb
-
Thiodicarb
structure -
-
CAS No:
59669-26-0
-
Formula:
C10H18N4O4S3
-
Chemical Name:
Thiodicarb
-
Synonyms:
6-Oxa-3,9-dithia-2,4,7-triazadec-7-enoic acid,2,4,8-trimethyl-5-oxo-,[1-(methylthio)ethylidene]azanyl ester;Ethanimidothioic acid,N,N′-[thiobis[(methylimino)carbonyloxy]]bis-,dimethyl ester;UC 51762;Bismethomyl thioether;Larvin;Thiodicarb;Lepicron;CGA 45156;Dicarbasulf;Semevin;Liushuanwei;65154-62-3;72424-66-9;78876-59-2;149440-58-4
- Categories:
-
CAS No:
Description
Thiodicarb appears as colorless to pale tan crystals. Non corrosive. Used as an insecticide.
Thiodicarb appears as colorless to pale tan crystals. Non corrosive. Used as an insecticide.
Thiodicarb Basic Attributes
354.47
354.47
261-848-7
K6S32206KF
2757|2588
DTXSID0032578
Colorless crystals|White to light tan crystalline powder (solid)|Colorless to light tan crystals
Characteristics
159.70000
1.52
1.44 g/cm3 @ Temp: 20 °C
173 °C
433.8±28.0 °C at 760 mmHg
216.2±24.0 °C
1.575
35 mg l -1 (25 °C)
0-6°C
5.1×10 -3 Pa (20 °C)
Oral-Rat LD50: 66 mg/kg
Combustion produces toxic nitrogen oxide and sulfur oxide gas
Slightly sulfurous odor
Henry's Law constant = 1.1X10-6 atm-cu m/mol at 25 °C (est VP/WS)
Pale tan crystals /Technical grade/|Stable at pH 6, rapidly hydrolysed at pH 9 and slowly at pH 3. Aqueous suspensions are decomposed by sunlight. Stable up to 60 °C.|Hydroxyl radical reaction rate constant = 1.3X10-11 cu cm/mole-sec at 25 °C (est)
Hydrolyzed by strong acid or base.
Carbamates
A carbamate derivative. 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
III
6.1(b)
2757
3
25-26
28-36/37-45
KJ4301050
T+
The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials
Stable under recommended storage conditions.|Stable under normal storage conditions, but degrades at temperatures above 60 °C.
P260-P273-P284-P310
H301-H330-H400
Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U410, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.|Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material. Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber; Contaminated packaging: Dispose of as unused product.
Incompatible materials: Strong oxidizing agents.|Aqueous suspensions are decomposed by sunlight.|Incompatible with acidic and alkaline substances, certain heavy-metal oxides, and salts of certain fungicides such as maneb, mancozeb (except WP formulations), cuprammonium carbonate, or Bordeaux mixtures. Not miscible with vegetable oil diluents.
USEPA; Office of Prevention, Pesticides and Toxic Substances; Reregistration Eligibility Decision (RED) for Thiodicarb EPA 738-R-98-022 (December 1998). The RED summarizes the risk assessment conclusions and outlines any risk reduction measures necessary for the pesticide to continue to be registered in the USA.[Available from, as of January 31, 2017: http://www.epa.gov/pesticides/reregistration/status.htm]
Excerpt from ERG Guide 151 [Substances - Toxic (Non-combustible)]: Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Containers may explode when heated. Runoff may pollute waterways. (ERG, 2016)
|Danger|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|P260, P264, P270, P271, P273, P284, P301+P310, P304+P340, P310, P320, P321, P330, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 132 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P201, P202, P260, P264, P270, P281, P301+P310, P305+P351+P338, P307+P311, P308+P313, P314, P321, P330, P337+P313, P405, and P501
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)
Excerpt from ERG Guide 151 [Substances - Toxic (Non-combustible)]: 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. Cover with plastic sheet to prevent spreading. 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 151 [Substances - Toxic (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)|Eye/face protection: Face shield and safety glasses. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).|Skin protection: Handle with gloves.|Body Protection: Complete suit protecting against chemicals. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.|Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a full-face particle respirator type N100 (US) or type P3 (EN 143) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Nonflammable.
Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.|Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.|Fire extinguishing media: Dry chemical, carbon dioxide, foam or water spray.
ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Wear respiratory protection. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.
ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Wear respiratory protection. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided.|Precautions for safe handling: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Provide appropriate exhaust ventilation at places where dust is formed. Normal measures for preventive fire protection.|Appropriate engineering controls: Avoid contact with skin, eyes and clothing. Wash hands before breaks and immediately after handling the product.|Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.|SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker.
/GUIDE 131 FLAMMABLE LIQUIDS - TOXIC/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion and poison hazard indoors, outdoors or in sewers. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. /Carbamate pesticide, liquid, flammable, poisonous; Carbamate pesticide, liquid, flammable, toxic; Carbamate pesticide, liquid, poisonous, flammable; Carbamate pesticide, liquid, toxic, flammable/|/GUIDE 131 FLAMMABLE LIQUIDS - TOXIC/ Health: TOXIC; may be fatal if inhaled, ingested or absorbed through skin. Inhalation or contact with some of these materials will irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution. /Carbamate pesticide, liquid, flammable, poisonous; Carbamate pesticide, liquid, flammable, toxic; Carbamate pesticide, liquid, poisonous, flammable; Carbamate pesticide, liquid, toxic, flammable/|/GUIDE 131 FLAMMABLE LIQUIDS - TOXIC/ Public Safety: CALL Emergency Response Telephone Number on Shipping Paper first. If Shipping Paper not available or no answer, refer to appropriate telephone number listed on the inside back cover. As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind, uphill and/or upstream. Ventilate closed spaces before entering. /Carbamate pesticide, liquid, flammable, poisonous; Carbamate pesticide, liquid, flammable, toxic; Carbamate pesticide, liquid, poisonous, flammable; Carbamate pesticide, liquid, toxic, flammable/|/GUIDE 131 FLAMMABLE LIQUIDS - TOXIC/ Protective Clothing: 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. /Carbamate pesticide, liquid, flammable, poisonous; Carbamate pesticide, liquid, flammable, toxic; Carbamate pesticide, liquid, poisonous, flammable; Carbamate pesticide, liquid, toxic, flammable/|For more DOT Emergency Guidelines (Complete) data for Thiodicarb (16 total), please visit the HSDB record page.
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. Carbamate pesticide, solid, toxic; carbamate pesticide, liquid, flammable, toxic, flashpoint less than 23 °C; carbamate pesticide, liquid, toxic, flammable, flashpoint 23 °C or more; and carbamate pesticide, liquid, toxic are included on the dangerous goods list. /Carbamate pesticide, solid, toxic; carbamate pesticide, liquid, flammable, toxic, flashpoint less than 23 °C; carbamate pesticide, liquid, toxic, flammable, flashpoint 23 °C or more; and carbamate pesticide, liquid, toxic/|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. Carbamate pesticide, solid, toxic; carbamate pesticide, liquid, flammable, toxic, flashpoint less than 23 °C; carbamate pesticide, liquid, toxic, flammable, flashpoint not less than 23 °C; and carbamate pesticide, liquid, toxic are included on the dangerous goods list. /Carbamate pesticide, solid, toxic; carbamate pesticide, liquid, flammable, toxic, flashpoint less than 23 °C; carbamate pesticide, liquid, toxic, flammable, flashpoint not less than 23 °C; and carbamate pesticide, liquid, toxic/
Thiodicarb is ... primary eye irritant in rabbits ... Thiodicarb induced a weak dermal sensitization reaction in guinea pigs.
U410; A toxic waste when a discarded commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or 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 100 lb or 45.4 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV.D.3.b).
U410; As stipulated in 40 CFR 261.33, when thiodicarb, 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 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).
Toxicity
highly toxic
IDENTIFICATION AND USE: Thiodicarb is a solid. It is used as insecticide, and as a seed treatment/protectant. HUMAN EXPOSURE AND TOXICITY: It is a probable human carcinogen. ANIMAL STUDIES: Instillation in rabbit eyes resulted in slight irritation. Thiodicarb produced no irritation during the primary dermal irritation study in rabbits. Thiodicarb induced a weak dermal sensitization reaction in guinea pigs. Marked systemic organ toxicity was noted in rats after exposure to thiodicarb. In rats it decreased red blood cell cholinesterase activity, and decreased hemoglobin. In dogs it decreased hematocrit and hemoglobin. Skin application in rabbits caused macrocytic anemia, erythema, and edema. Other dermal study in rabbits described decreased erythrocytes, decreased hemoglobin, and decreased body weight. Male rats treated with thiodicarb displayed an increased incidence of interstitial cell tumors in the testes compared to the concurrent control males, and the incidence was also greater than the historical control. In mice it produced increased incidences of hepatocellular tumors in both sexes. Developmental studies in rats demonstrated decreased fetal body weight and an increase in the number of litters and fetuses with developmental variations. Thiodicarb did not induce a mutagenic response in the Ames assay, with or without metabolic activation. Thiodicarb induced dose-related increased mutant frequencies in mouse lymphoma TK+/- cells, with and without metabolic activation and is considered to have an equivocal weak effect in the mouse lymphoma forward mutation assay. Thiodicarb, with or without metabolic activation, did not cause a clastogenic response in the chromosomes of Chinese hamster ovary cells. Thiodicarb is considered inactive in the primary rat hepatocyte unscheduled DNA synthesis assay. ECOTOXICITY STUDIES: Thiodicarb is moderately toxic to bees as direct treatment, but is not toxic after spray residues have dried.
LD50 Rat (male) oral 46.5-398 mg/kg|LD50 Rat (female) oral 39.1-248 mg/kg|LD50 Mouse (male) oral 73 mg/kg|LD50 Mouse (female) oral 79 mg/kg|For more Non-Human Toxicity Values (Complete) data for Thiodicarb (15 total), please visit the HSDB record page.
/AQUATIC SPECIES/ The inhibitory effects of four carbamate insecticides, methomyl, thiodicarb, carbofuran and carbosulfan, on acetylcholinesterase (AChE) of male and female Carassius auratus were investigated in the laboratory. Kinetic constants, biomolecular rate constant (k(i)), carbamylation rate constant (k2) and decarbamylation rate constant (k3) were determined in vitro. The ratios of bimolecular rate constant (female/male) for AChE reacting with methomyl, thiodicarb, carbofuran and carbosulfan were 1.03, 2.44, 1.03 and 1.106, respectively. The k(i) of AChE for thiodicarb was significantly higher in female fish than in male fish (P<0.05). The ratios of carbamylation rate constant (female/male) for methomyl, thiodicarb, carbofuran and carbosulfan were 1.18, 4.29, 3.53, and 2.07, respectively. The k2 values of AChE for the above four carbamates were significantly higher in females than in males. The ratios of the decarbamylation rate constant (female/male) for methomyl, thiodicarb, carbofuran and carbosulfan were 1.02, 1.39, 1.06, and 1.98, respectively. Only for carbosulfan, the decarbamylation rate of AChE was significantly higher in the female than in the male, indicating that AChE of females inhibited by carbosulfan recovered more quickly than that of males. The above results suggest that the female in the sensitivity of AChE to carbamates was different from the male fish.|/OTHER TERRESTRIAL SPECIES/ Bee: Moderately toxic as direct treatment; not toxic after spray residues have dried.
Thiodicarb's production may result in its release to the environment through various waste streams; its use as an insecticide and molluscicide(1) will result in its direct release to the environment(SRC).
TERRESTRIAL FATE: Based on a classification scheme(1), an average Koc value of 351(2), indicates that thiodicarb is expected to have moderate mobility in soil(SRC). Volatilization of thiodicarb from moist soil surfaces may be expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.1X10-6 atm-cu m/mole(3), based upon its vapor pressure, 4.3X10-5 mm Hg(4), and water solubility, 19.1 mg/L(5). Thiodicarb is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). Thiodicarb degrades rapidly in aerobic soil, with a reported half-life of 1.5 days in sandy loam soil(4), suggesting that biodegradation is an important environmental fate process in soil(SRC). Thiodicarb degrades rapidly into methomyl under most environmental conditions which is more mobile, persistent, and toxic than the parent compound(4).|FIELD STUDY: Thiodicarb has a half-life of 18 days resulting from a field dissipation study in Washington sandy loam soil; both thiodicarb and its degradate, methomyl, showed greater leaching compared with soil accumulation upon repeated applications(1). Field dissipation half-lives of 2 to 8 days have also been reported(2).|AQUATIC FATE: Based on a classification scheme(1), an average Koc value of 351(2), indicates that thiodicarb may adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected to be slow(3) based upon an estimated Henry's Law constant of 1.1X10-6 atm-cu m/mole(4), based upon its vapor pressure, 4.3X10-5 mm Hg(5), and water solubility, 19.1 mg/L(6). Using this Henry's Law constant and an estimation method(4), volatilization half-lives for a model river and model lake are 60 days and 1.3 years, respectively(SRC). According to a classification scheme(7), a BCF of 5.7(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Thiodicarb degrades under anaerobic conditions in aqueous environments with a reported half-life of 3 hours(4).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), thiodicarb, which has a vapor pressure of 4.3X10-5 mm Hg at 20 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase thiodicarb 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 9.7 hours(3), calculated from its rate constant of 1.3X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(4). Particulate-phase thiodicarb may be removed from the air by wet and dry deposition(SRC). Thiodicarb contains chromophores that absorb at wavelengths >290 nm(5) and, therefore, is susceptible to direct photolysis by sunlight(SRC). Reported aqueous and soil photolysis half-lives for thiodicarb are 8 days and 37 days, respectively(2).
The rate constant for the vapor-phase reaction of thiodicarb with photochemically-produced hydroxyl radicals has been estimated as 1.3X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 9.7 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(2). Thiodicarb has hydrolysis half-lives of 78 days, 32 days, and 12 hours at pH values of 5, 7, and 9, respectively(3). Thiodicarb contains chromophores that absorb at wavelengths >290 nm(4) and, therefore, is susceptible to direct photolysis by sunlight(SRC). Reported aqueous and soil photolysis half-lives for thiodicarb are 8 days and 37 days, respectively(3).
In a fish bioaccumulation study, acetic acid was the major metabolite in fish tissue and 46-74% of the accumulated residues in the fish tissues were eliminated after 28 days(1). A whole body BCF of 5.7 was reported for thiodicarb in bluegill fish (Lepomic macrochirus) exposed for 28 days, in the EPA bioconcentration guideline 165-4/OPPTS 950.1730 test(2). According to a classification scheme(3), this BCF suggests the bioconcentration in aquatic organisms is low.
346.74 L/kg|Thiodicarb has Koc values of 64 to 1,167, with a mean value of 351, reported for sand, silt loam, clay, sand, and sandy loam(1-3). Thiodicarb has a soil distribution coefficient, Kd = 3.30(4). According to a classification scheme(5), the average Koc value suggests that thiodicarb is expected to have moderate mobility in soil.
The Henry's Law constant for thiodicarb is estimated as 1.1X10-6 atm-cu m/mole(SRC) derived from its vapor pressure, 4.3X10-5 mm Hg(1), and water solubility, 19.1 mg/L(2). This Henry's Law constant indicates that thiodicarb is expected to volatilize slowly from water surfaces(3). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(3) is estimated as 63 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(3) is estimated as 1.3 years(SRC). Thiodicarb's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may occur slowly(SRC). Thiodicarb is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).
No reports of ground water monitoring studies that included thiodicarb were found in searches of the United States Geological Survey (USGS) online National Water Quality Assessment Data Warehouse (NAWQA) database, nor the EPA publication, EPA Pesticides in Ground Water, A Compilation of Monitoring Studies 1971-1991 National Summary(1).|SURFACE WATER: Water quality data compiled from the Retrieval (STORET) Data Warehouse report 2006 monitoring data from the Idaho State Department of Agriculture indicating that thiodicarb was not detected in surface water samples collected from April 2006 to July 2006(1). Water quality data compiled from the Retrieval (STORET) Data Warehouse report 2013, 2014, and 2015 monitoring data from the California Department of Water Resources indicating that thiodicarb's major degradation product, methomyl, was detected in surface water samples, at concentrations ranging from 0 to 1.2 ug/L, collected in March, June, and Sept 2013, Feb, March, Apr, Jun and Aug 2014, and March and June 2015(1).
Thiodicarb residue was detected in unwashed, washed, and washed and salted potato tuber samples at concentrations of 0.008 to 0.038 mg/kg, but was not detected in peeled samples, potato samples were collected from local markets in Egypt in 2013(1).
Occupational exposure to thiodicarb may occur through inhalation and dermal contact with this compound at workplaces where thiodicarb is produced or used. (SRC)
Drug Information
Metabolic studies were performed in rats using single low and single high doses of radiolabeled thiodicarb. The major routes of elimination were expiration (CO2 and acetonitrile) and urination. Tissue residues contained 7-9% of the dose at 7 days post dose and may reflect the metabolism of (14)C-acetonitrile into the body's C-2 and C-1 pools and subsequent interaction with, or incorporation into natural products.
Metabolic studies were performed in rats using single low and single high doses of radiolabeled thiodicarb. The major routes of elimination were expiration (CO2 and acetonitrile) and urination. Tissue residues contained 7-9% of the dose at 7 days post dose and may reflect the metabolism of (14)C-acetonitrile into the body's C-2 and C-1 pools and subsequent interaction with, or incorporation into natural products. The major terminal metabolites of thiodicarb in the rat are CO2 and acetonitrile. The major urinary metabolite is a labile unknown that represents 50% of the urinary radiolabel. No acetamide was detected in any of the tissues. The RBCs contained only residue that cannot be extracted by organic solvents or water, indicating the presence of radiolabel incorporated into natural products or of material tightly bound to hemoglobin.|In a metabolism study in monkeys, some thiodicarb (syn, syn-isomer) radiolabel was converted via in vivo metabolism to syn-methomyl and subsequently isomerized to anti-methomyl, with ~0.8-1.0% (lower limit) to 2.6-3.3% (upper limit) by weight of thiodicarb being converted to acetamide and excreted in the urine.
Excerpt from ERG Guide 151 [Substances - Toxic (Non-combustible)]: Highly toxic, may be fatal if inhaled, swallowed or absorbed through skin. 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 151 [Substances - Toxic (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)
Ensure that a clear airway exists. Intubate the patient and aspirate the secretions with a large bore suction device if necessary. Administer oxygen by mechanically assisted pulmonary ventilation if respiration is depressed. Improve tissue oxygenation as much as possible before administering atropine, so as to minimize the risk of ventricular fibrillation. In severe poisonings, it may be necessary to support pulmonary ventilation mechanically for several days. /N-methyl carbamate insecticides/|Administer atropine sulfate intravenously or intramuscularly if intravenous injection is not possible. Atropine can be administered in small volume doses through an endotracheal tube if initial IV access is difficult to obtain. Carbamates may reverse with smaller dosages of atropine than those required to reverse organophosphates, though the required dosage is still considerably larger than that required to atropinize a non-poisoned patient. A common dosing pitfall is giving too little atropine initially to achieve timely atropinization. Severely poisoned individuals may exhibit remarkable tolerance to atropine and require large doses. ... The objective of atropine antidotal therapy is to antagonize the effects of excessive concentrations of acetylcholine at end-organs having muscarinic receptors. Atropine does not reactivate acetylcholinesterase (AChE) or accelerate excretion or breakdown of carbamate. Multiple doses of atropine may be necessary, as recrudescence of poisoning can occur if tissue concentrations of toxicant remain high when the antidotal effect wears off. Atropine is effective against muscarinic manifestations, but is ineffective against nicotinic actions, specifically muscle weakness and twitching, and respiratory depression. Despite these limitations, atropine is often a lifesaving agent in N-methyl carbamate poisonings. Reassess the clinical situation after an adequate loading dose has been given. If symptoms persist, but the history is consistent with carbamate poisoning, then continue atropine therapy. However, if the clinical picture is unclear, clinicians should reassess and consider alternative causes of poisoning, such as pyrethroid insecticide poisoning, which may present a similar clinical picture. ... Reversal of muscarinic manifestations, rather than a specific dosage, is the object of atropine therapy. /N-methyl carbamate insecticides/|Urine sample. Save a urine sample for metabolite analysis if there is need to identify the agent responsible for the poisoning. /N-methyl carbamate insecticides/|Consider pralidoxime in cases of mixed carbamate/organophosphate poisoning and cases of an unknown pesticide with muscarinic symptoms on presentation ... . Pralidoxime has been used in some cases of carbamate poisoning, although other cases have resolved from supportive care alone. Pralidoxime is probably of little value in N-methyl carbamate poisonings and is not indicated in isolated carbamate poisonings. Atropine alone usually is effective. /N-methyl carbamate insecticides/|For more Antidote and Emergency Treatment (Complete) data for Thiodicarb (15 total), please visit the HSDB record page.
/CASE REPORTS/ ... A 40-year-old woman was found dead in her car. Empty packages of medicines and an open bottle of Larvin containing thiodicarb were found near her body. No signs of violence nor traumatic injuries were noticed upon autopsy, and police investigations strongly suggested a suicide. Systematic toxicological analysis performed on postmortem specimens revealed the presence of various sedatives, hypnotics, and antipsychotic drugs in blood, urine, and gastric content. Some of the compounds identified were determined at blood concentrations well above the known therapeutic concentrations: zolpidem (2.87 mg/L), bromazepam (2.39 mg/L), nordazepam (4.21 mg/L), and levopremazine (0.64 mg/L). Specific analysis of thiodicarb and of its methomyl metabolite was then performed on all fluids and tissues collected during autopsy by liquid chromatography ion trap tandem mass spectrometry (LC-MS-MS). The anticholinesterase capacity of blood, urine, and gastric content collected at autopsy was 83%, 82%, and 32%, respectively (normal value: 0%). The presence of thiodicarb in the bottle found near the body corroborates the hypothesis of an intake of that compound. Although thiodicarb was only detected in gastric content (24.3 mg/L), its methomyl metabolite was quantified in most postmortem tissues and fluids: gastric content (19.9 mg/L), peripheral blood (0.7 mg/L), urine (8.5 mg/L), bile (2.7 mg/L), liver (0.7 mg/kg), kidney (1.7 mg/kg), lung (1.5 mg/kg), brain (9.3 mg/kg), and heart (3.6 mg/kg).
thiodicarb
Thiodicarb Use and Manufacturing
Stir a certain amount of pyridine and xylene in the main reactor by means of metdolcarb synthesis, and reduce the temperature to a predetermined value with ice brine, then at this temperature, slowly add the prepared sulfur dichloride solution to the reaction In the reactor, continue the reaction for a certain period of time after adding, then add metoprolol to raise the temperature to a predetermined value, after stirring the reaction for a certain period of time, cool the reaction solution to below 20 ℃, slowly add a certain amount of water, stir for more than 10min, stop stirring, The reaction was filtered, washed and filtered, repeated 3 times, the filter cake was weighed, and dried at below 60 ℃ to obtain thiodimethadol product. The filtrate is separated into layers, the xylene layer is ready for use, the aqueous layer is extracted with dichloromethane, the extract is evaporated to dissolve, the methotrexate is recovered, a certain amount of solid alkali is added to the mother liquor, fully stirred, and allowed to stand for separation, the oil layer and the xylene layer are combined , And sent to the rectification tower to recover pyridine and xylene. After industrial tests, the product quality is good and the yield is high. There are also reports that using pyridine as a solvent, methacarb is interacted with S2Cl2 (or SCl2-S2Cl2) to produce thiodicarb with a yield of 91.3%. Synthesized by metdaloxime. Produced by metdolcarb. Intermediate of metdaloxime (methylthioacetaldehyde oxime, see the preparation method of medocarb) in the presence of triethylamine and N-methylformyl fluoride sulfide. Desulfiram was obtained with a yield of 92%.
Insecticide.
(1989) 950,000 lbs ai/yr|1,150,000 lbs ai used annually in the United States and usage appears to be increasing.
Larvin Brand Technical Thiodicarb Insecticide (Bayer Cropscience LP): Active ingredient: Thiodicarb 95.0%.|Aeris Seed-Applied Insecticide/Nematicide (Bayer Cropscience LP): Active ingredient: Thiodicarb 95.0%.|Aqueous flowable, water dispersible granule, wettable powder, and flowable concentrate for seed treatments.|Technical grade (96%), manufacturing product (90%), end use product (1.75% to 80%); liquid (unspecified, 90%, 96%), flowable concentrate (23.6%, 34%), granular (4%), pelleted/tableted (1.75%), water dispersible granules (dry flowable, 80%), wettable powder (75.2%).|Premix Partners: Imidacloprid.
The WHO Recommended Classification of Pesticides by Hazard identifies Thiodicarb (technical grade) as Class II: moderately hazardous; Main Use: insecticide.|Thiodicarb meets the requirments for classification as a Restricted Use Pesticide.
A liquid chromatography method with post-column photoinduced chemiluminescence (PICL) detection is proposed for the simultaneous determination of eight carbamate pesticides, namely aldicarb, butocarboxim, ethiofencarb, methomyl, methiocarb, thiodicarb, thiofanox and thiophanate-methyl. After chromatographic separation, quinine (sensitizer) was incorporated and the flow passed through an UV lamp (67 s of irradiation time) to obtain the photoproducts, which reacted with acidic Ce(iv) and provided a CL emission. The PICL method showed great selectivity for carbamate pesticides containing sulphur in their chemical structure. A solid-phase extraction process increased sensitivity (limits of detection ranging from 0.06 to 0.27 ng/mL) and allowed the carbamate pesticides in surface and ground water samples to be determined, with recoveries in the range 87-110% (except for thiophanate-methyl, whose recoveries were between 60 and 75%). The intra- and inter-day precision was evaluated, with relative standard deviation ranging from 1.1 to 7.5% and from 2.6 to 12.3%, respectively. ...|A high performance liquid chromatography with fluorescence (HPLC-F) detector was examined to simultaneous determination of airborne carbamates in the workplace of manufactory. The OVS-2 air sampling tube filled with glass fiber filter or quartz fiber and combined filter/XAD-2 were evaluated to collect nine commonly used carbamates (Carbofuran, Isoprocarb, Methomyl, Metolcarb, Thiodicarb, Carbaryl, Oxamyl, Methiocarb, and Prpoxur) from the air of manufactory in high humidity country. After being extracted with acetonitrile from sampling tubes, the carbamates were determined by high performance liquid chromatography with fluorescence detection posterior to on-line derivatization. The collection of carbamates and the recovery of extraction from glass wool fiber in several concentration levels, and from quartz filter were evaluated. The storage stability of carbamates was also tested. Results indicated that the HPLC-fluorescence method offers satisfactory resolution and sensitivity in carbamate analysis. With the glass fiber filter and combined filter/XAD-2, the Carbofuran, Isoprocarb, Methomyl, Metolcarb, and Thiodicarb were stable for a 28-day storage test, Carbaryl and Oxamyl for 14 days, and Methiocarb and Prpoxur for 7 days. All of these pesticides were with detection limit of 3 ug/cu m. It is suited for environmental monitoring. The airborne carbamates in different areas of the manufactory were measured.|A biosensor based on alfalfa sprout (Medicago sativa) homogenate as a source of peroxidase is proposed for the determination of thiodicarb by square-wave voltammetry. This enzyme was immobilized in self-assembled monolayers of l-cysteine on a gold electrode. Several parameters were investigated to evaluate the optimum conditions for operation of the biosensor. The analytical curve was linear for thiodicarb concentrations of 2.27 x 10(-6) to 4.40 x 10(-5) mol/L with a detection limit of 5.75 x 10(-7) mol/L. The lifetime of the Au-alfalfa sprout-SAMs was 20 days (at least 220 determinations). The average recovery of thiodicarb from samples of vegetable extracts ranged from 99.02 to 101.04%. The results obtained for thiodicarb in vegetable extracts using the proposed method are in close agreement with those using a high performance liquid chromatography procedure at the 95% confidence level.|A high-performance liquid chromatography-fluorescence detection method was developed for the simultaneous determination of thiodicarb and its degradation product methomyl in animal-derived food products, including chicken muscle, beef, pork, table eggs, and milk. Thiodicarb is known to degrade during analysis; therefore, a thorough investigation was carried out, revealing that thiodicarb degrades to methomyl immediately after spiking into a matrix of animal-derived food products. Consequently, thiodicarb was determined as the sum of the parent compound and methomyl. Samples were extracted with acetonitrile and sodium salts, and purified using solid-phase extraction (SPE). The limits of detection (LODs) and quantification (LOQs) were 0.0013 and 0.004 mg/kg, respectively, for both analytes in various matrices. Seven-point external calibration curves were obtained, and they showed excellent linearity with determination coefficients (R2) >/= 0.999 for all tested matrices. The method was validated at three fortification levels (LOQ, LOQx2, and LOQx10) in triplicate with average recoveries ranging from 84.24 to 112.8% (for methomyl) and relative standard deviations (RSDs) = 6.5% in all matrices. The converted recoveries of thiodicarb in various matrices ranged from 74.80 to 107.80% with RSDs = 4.5%. The identities of both compounds in standard solutions and for recovery were confirmed using liquid chromatography-tandem mass spectrometry (LC-MS/MS). The developed method was further validated by accurate reproduction at another laboratory. Finally, the method was applied to market samples collected from different areas (and, in the case of milk, different brands), and none of the samples tested positive for thiodicarb or methomyl. In conclusion, the developed method can be successfully applied for a single-run analysis of thiodicarb and methomyl in livestock products.
Agrochemicals -> Insecticides|Environmental transformation -> Pesticides (parent, predecessor)
Thiodicarb has known environmental transformation products that include Methomyl oxime.
Computed Properties
Molecular Weight:354.5
XLogP3:1.7
Hydrogen Bond Acceptor Count:9
Rotatable Bond Count:8
Exact Mass:354.04901859
Monoisotopic Mass:354.04901859
Topological Polar Surface Area:160
Heavy Atom Count:21
Complexity:393
Undefined Bond Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Recommended Suppliers of Thiodicarb
-
CN
5 YRS
Business licensedTrader Supplier of Intermediates,Building blocks,API,Silicones,Peptides,Lab chemicals,Biochemicals,Pharmaceuticals,Screening Compounds,Food Additives -
CN
3 YRS
Business licensedTrader Supplier of reference material,reference standards,Reference Standard Materials,ICP & ICP-MS Single/Mix Standards,Analytical standards,Lab reagents,Lab Chemicals,Fine chemicals,Bioreagents
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