ALDICARB

ALDICARB Basic information
Product Name:ALDICARB
Synonyms:aldicarb (ISO) 2-methyl-2-(methylthio)propanal-O-(N-methylcarbamoyl)oxime;Aldicarb solution;2-Methyl-2-(methylthio)propanal O-(methylcarbamoyl)oxime;NSC 379586;10 -100 g;Aldicab;(1E)-2-Methyl-1-(([(methylamino)carbonyl]oxy)imino)-2-(methylsulfanyl)propane;2-Methyl-2-(methylthio)propanal, O-((methylamino)carbonyl)oxime
CAS:116-06-3
MF:C7H14N2O2S
MW:190.26
EINECS:204-123-2
Product Categories:INSECTICIDE
Mol File:116-06-3.mol
ALDICARB Structure
ALDICARB Chemical Properties
Melting point 99-100° with dec >100°
density d425 1.195
vapor pressure 1.3×10-2 Pa (25 °C)
refractive index 1.4920 (estimate)
Fp 2 °C
storage temp. APPROX 4°C
solubility DMSO: slightly soluble; Methanol: slightly soluble
form neat
pka11.7
Water Solubility 4.9 g l-1(pH 7,20 °C)
BRN 2209304
IARC3 (Vol. 53) 1991
EPA Substance Registry SystemAldicarb (116-06-3)
Safety Information
Hazard Codes T+,N,Xn,F
Risk Statements 24-26/28-50/53-36-20/21/22-11
Safety Statements 22-36/37-45-60-61-26-16
RIDADR 2757
WGK Germany 3
RTECS UE2275000
HazardClass 6.1(a)
PackingGroup I
HS Code 29309090
Hazardous Substances Data116-06-3(Hazardous Substances Data)
ToxicityLD50 in male and female rats (mg/kg): 0.81-0.93, 0.67-1.20 orally; LC50 (96 hr) in rainbow trout, bluegill sunfish (ppb): 560-580, 50-100 (Baron, 1988)
MSDS Information
ALDICARB Usage And Synthesis
DescriptionAldicarb is a carbamate pesticide that reversibly inhibits acetylcholinesterase. It is the active ingredient in mixtures used to control insect, mite, and nematode pests in agriculture. Aldicarb has a high acute mammalian toxicity (LD50 = 0.3-0.5 mg/kg) following oral or parenteral administration. Aside from its use as a pesticide, aldicarb has applications as an acetylcholinesterase inhibitor for research purposes.
Chemical PropertiesAldicarb is a noncombustible, white crystalline solid with a slight sulfurous odor.It is not compatible with alkaline materials and is non-corrosive to metals and plastics. It is sparingly soluble in water, but soluble in acetone, xylene, ethyl ether, toluene, and other organic solvents. Aldicarb has been classifi ed as an RUP and hence should only be used by trained and certifi ed workers. Aldicarb is used to control mites, nematodes, and aphids and is applied directly to the soil. It is used widely on cotton, peanut, and soybean crops. In the mid-1980s, there were highly publicized incidents in which misapplication of aldicarb contaminated cucumbers and watermelons and led to adverse effects in people. Aldicarb is metabolized in the liver of mammals fi rst into aldicarb sulfoxide and later into aldicarb sulfone.
UsesAldicarb is a broad-spectrum, systemic carbamate insecticide used to control nema-todes in soil and a variety of insects and mites on citrus crops, dry beans, grain, sorghum, ornamentals, pecans, peanuts, potatoes, seed alfalfa, soybeans, sugar beets, sugarcane, sweet potatoes, and tobacco.
UsesAldicarb is a soil applied systemic oxime carbamate insecticide with both contact and oral activities. It controls a broad spectrum of chewing and sucking insects, mites and nematodes on a wide variety of field, fruit and vegetables crops such as cotton, citrus, potatoes, sugar beet and peanuts.
PreparationAldicarb is prepared by treating isobutene with nitrosyl chloride, treating the resulting dimeric adduct with sodium methyl sulfide, and converting the resulting oxime to the carbamate with methyl isocyanate. Warning: the dimeric isobutene nitrosochloride is unstable and decomposes explosively at 94 °C. The oxime and end product also decompose vigorously above 140 and 160 °C, respectively.
DefinitionChEBI: The oxime carbamate resulting from the addition of 2-methyl-2-(methylsulfanyl)propanaldoxime to methyl isocyanate. A member of the class of oxime carbamate insecticides, aldicarb is a mixture of E and Z isomers; it is not nown which isomer is more active.
General DescriptionWhite crystals with a slightly sulfurous odor. Commercial formulations are granular Used as an insecticide, acaricide, and nematocide.
Air & Water ReactionsSlightly water soluble.
Reactivity ProfileALDICARB is a carbamate ester. ALDICARB decomposes at temperatures greater than 212° F. ALDICARB is incompatible with highly alkaline substances. ALDICARB is rapidly converted by oxidizing agents.
Health HazardAldicarb is the most potent of the commercially available carbamate pesticides and is an unusual source of acute human poisoning. Aldicarb has severe systemic toxicity to animals and humans. Aldicarb is a cholinesterase inhibitor that prevents the breakdown of acetylcholine in the synapse. In the case of severe poisoning, the victim dies of respiratory failure. The primary route of human exposure to aldicarb is consumption of contaminated food and water from contaminated wells. Occupational exposure to high levels of aldicarb is due to product handling, and most cases of aldicarb poisoning occur from loading and application of the pesticide. Aldicarb is extremely toxic both through the oral and dermal route. Absorption from the gut is rapid and almost complete. When administered in oil or other organic solvents, aldicarb is absorbed rapidly through the skin. Its skin toxicity is roughly 1000 times that of other carbamates. In humans, the onset of symptoms is rapid (15 min to 3 h). Symptoms disappear in 4–12 h.The acute oral LD50 of aldicarb in rats, mice, guinea pigs, and rabbits ranges from 0.5 to 1.5 mg/kg when administered in a liquid or oil form. The toxicities of the dry granules are distinctly lower (LD50 7.0 mg/kg), though still highly toxic. Aldicarb is a cholinesterase inhibitor and therefore can result in a variety of symptoms including weakness, blurred vision, headache, nausea, tearing, sweating, and tremors. At very high concentrations, aldicarb causes paralysis, respiratory system damage, eventually leading to the death of the exposed worker. There is very little evidence of chronic effects from aldicarb exposure. Rats and dogs fed low doses of aldicarb for 2 years showed no signifi cant adverse effects. One epidemiological study suggested a possible link between low-level exposure and immunological abnormalities. The result of this study, however, has been widely disputed. Aldicarb administered to pregnant rats at very low levels (0.001–0.1 mg/kg/day) depressed AChE activity more in the fetuses than in the mother. The aldicarb was also retained in the mother’s body for longer periods than in non-pregnant rats. A three-generation study at doses of 0.05 and 0.10 mg/kg/day produced no signifi cant toxic effects, and in another study, a dose of 0.70 mg/kg/day produced no adverse effects. Thus, reproductive effects in humans are unlikely at expected exposure levels.
Fire HazardWhen heated to decomposition, ALDICARB emits very toxic fumes of nitrogen oxides and sulfur oxides. Incompatible with highly alkaline substances. Unstable in alkali; poor stability at 122F.
Agricultural UsesInsecticide, Nematicide, Acaricide: A U.S. EPA restricted Use Pesticide (RUP). Not approved for use in EU countries.
Trade nameTEMIC®; TEMIK®; OMS 771®; TERNIC®; TEMIK 10 G®
Safety ProfileDeadly poison by ingestion, skin contact, subcutaneous, and possibly other routes. Human mutation data reported. Questionable carcinogen. A powerful systemic poison. In 1985 over 150 people in California exhibited toxic effects from eating watermelons contaminated with aldicarb. When heated to decomposition it emits very toxic fumes of NOx and SOx
Potential ExposureExposure to aldicarb and aldicarb sulfoxide and sulfone will occur mainly through the ingestion and contaminated drinking water derived from contaminated ground water as well as contaminated food.
Environmental FateAldicarb and its degradation products are generally very soluble in water and mobile in soil. Adsorption in soil is primarily to organic matter, so leaching is most exten- sive in sandy or sandy loam soils. Aldicarb is very persistent in groundwater, typi- cally degrading to nontoxic products with a half-life between a few weeks to as long as several years. The primary mode of degradation is chemical hydrolysis, with some microbial decay in shallow groundwater. In soils, the primary mode of degradation is oxidation by soil microorganisms and hydrolysis, depending on soil conditions.
Metabolic pathwayIn an aqueous buffer solution in the pH range 2.91 ? 5.51, the Cu(II) ion promotes the decomposition of aldicarb, forming the degradation products 2-methyl- 2-(methylthio)propionitrile and 2-methyl-2- (methylthio)propanal.
storageAldicarb should be kept stored in a dry, cool area, out of reach of children and animals, and away from food, feedstuffs, fertilizers, and seed.
ShippingUN2757 Carbamate pesticides, solid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials
DegradationAldicarb (1) is susceptible to alkaline hydrolysis. Under basic conditions (pH 9), aldicarb hydrolysed slowly with a DT50 of approximately 75 days. Cleavage of the oxime carbamate linkage to yield aldicarb oxime (2) and the aldicarb nitrile (3) was the primary degradation pathway. Aldicarb was stable to hydrolysis under acidic (pH 5) and neutral (pH 7) conditions (Andrawes, 1976a). Aldicarb also degraded in water under photolytic conditions (xenon lamp) with a DT50 of approximately 4 days (Das, 1990a). The major photolytic degradation products were aldicarb oxime (2) and aldicarb nitrile (3) (Andrawes, 1976b).
IncompatibilitiesStrong alkalis
Waste DisposalDo not discharge into drains or sewers. Dispose of waste material as hazardous waste using a licensed disposal contractor to an approved landfill. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal. Incineration with effluent gas scrubbing is recommended. In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers. In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers. Must be disposedproperly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office.
ALDICARB Preparation Products And Raw materials
Raw materialsSodium thiomethoxide-->METHYLISOCYANATE 1 X 500MG NEAT-->ALDICARB-OXIME-->BANOL
ALDICARB SOLUTION 100UG/ML IN METHANOL 1ML Aldicarb-d3 ALDICARB SULFOXIDE SOLUTION 100UG/ML IN ACETONITRILE 5X1ML ALDICARB SULFONE SOLUTION 100UG/ML IN METHANOL 5X1ML Aldicarb oxime sulfoxide,Aldicarb sulfoxide oxime ALDICARB SOLUTION 100UG/ML IN METHANOL 5X1ML ALDICARB (95-98%) ALDICARB SULFONE SOLUTION 100UG/ML IN METHANOL 5ML Nitrosoaldicarb ALDICARB SOLUTION 100UG/ML IN METHANOL 5ML ALDICARB-OXIME BANOL ALDICARB SULFOXIDE SOLUTION 100UG/ML IN ACETONITRILE 1ML ALDICARB SOLUTION 100 NG/MYL IN ENDOSULFAN ALCOHOL ALDICARB SULFONE SOLUTION 100UG/ML IN METHANOL 1ML ALDICARB SULFOXIDE SOLUTION 100UG/ML IN ACETONITRILE 5ML ALDICARB SULFOXIDE SOLUTION 100UG/ML IN TOLUENE 1ML

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