Aldicarb oxime

For research use only. Not for therapeutic Use.

  • CAT Number: M124067
  • CAS Number: 1646-75-9
  • Molecular Formula: C5H11NOS
  • Molecular Weight: 133.209
  • Purity: ≥95%
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Aldicarb oxime(CAS: 1646-75-9) appears as clear colorless,viscous liquid with an unpleasant sulfurous or musty odor. (NTP, 1992)


Catalog Number M124067
CAS Number 1646-75-9
Synonyms

2-methyl-2-(methylsulfanyl)propanaldoxime

Molecular Formula C5H11NOS
Purity ≥95%
Storage -20°C
IUPAC Name (NE)-N-(2-methyl-2-methylsulfanylpropylidene)hydroxylamine
InChI InChI=1S/C5H11NOS/c1-5(2,8-3)4-6-7/h4,7H,1-3H3/b6-4+
InChIKey ZFGMCJAXIZTVJA-GQCTYLIASA-N
SMILES CC(C)(C=NO)SC
Reference

[1]. Hum Exp Toxicol. 2000 Dec;19(12):657-62. doi: 10.1191/096032700672133218.<br />
Aldicarb poisoning.<br />
Ragoucy-Sengler C(1), Tracqui A, Chavonnet A, Daijardin JB, Simonetti M, Kintz P, Pileire B.<br />
Author information: (1)Biochemistry-Pharmacology-Toxicology, Centre Hospitalier Universitaire, Pointe &agrave; Pitre, Guadeloupe, French West Indies , France.<br />
Aldicarb (2-methyl-2(methylthio) propanal o-[(methylamino)-carbonyl] oxime) is a pesticide manufactured since 1965. This carbamate ester is sold under the tradename, Temik, and is used as insecticide and nematicide. The Environmental Protection Agency has classified aldicarb in the highest toxicity category and has defined a strict control for its delivery and use. In Brazil and the Caribbean island, aldicarb is illegally used as a household rodenticide with a widespread risk of poisoning. Our study presents the first review of aldicarb poisoning circumstances associated with clinical and analytical findings. Moreover, the oxime treatment is discussed. Eighteen patients with cholinergic symptoms admitted to the Emergency Unit and two deceased with a history of aldicarb poisoning were included in the study. As agricultural workers, only two of them could legally use Temik. Seventy percent of the patients was managed by the Emergency Mobil Unit. Serum cholinesterase activity was always lower than 30% of the normal range and aldicarb was identified by UV spectra and retention time after liquid chromatography separation. The most common muscarinic effect was diarrhea, the main nicotinic sign fasciculation and almost half of the poisoned patients had central nervous system (CNS) depression (Glasgow Coma Score lower than 8). Four patients had serious conduction abnormalities and two of them died. These results suggest that aldicarb intoxication is always severe. Oxime treatment did not produce side effects and should be recommended whenever the pesticide involved is unknown. Effective measures should be implemented to stamp out the illicit use of aldicarb.<br />
DOI: 10.1191/096032700672133218 PMID: 11291736 [Indexed for MEDLINE]<br />
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[2]. Environ Health Perspect. 1994 Dec;102 Suppl 11(Suppl 11):23-7. doi: 10.1289/ehp.94102s1123.<br />
A carbamate insecticide: a case study of aldicarb.<br />
Baron RL(1).<br />
Author information: (1)Baron Associates, Raleigh, NC 27636-3812, USA.<br />
Aldicarb, the active ingredient in the insecticide TEMIK, was introduced to the agricultural community over 25 years ago. It has been registered worldwide to control a wide variety of insect, mite, and nematode pests in agriculture. The toxicological research database supporting the registration and use of aldicarb was generated over more than 25 years and contains more than 280 animal studies on 12 species of animals, 2 clinical human trials, and over 20 human monitoring studies. This database, which includes biochemical aspects (metabolism and mode-of-action studies), acute toxicity and special short-term toxicity studies, long-term toxicity studies, and epidemiological observations in humans, serves as the starting point for the evaluation of the risks associated with the acceptance of levels of aldicarb residues in food and drinking water and for the more direct occupational exposure. This article highlights the available toxicological data and reviews worldwide regulation of aldicarb. Included in these discussions is a brief description of the toxicological end point upon which regulatory decisions have been based, namely acetylcholinesterase depression. Aldicarb, the N-methylcarbamic acid ester of 2-methyl-2-(methylthio) propionaldehyde oxime, was the first of a limited group of insecticidal oxime N-methylcarbamates that have properties distinct from N-methylcarbamates which have a phenolic constituent, instead of the oxime moiety. Aldicarb is highly water-soluble (approximately 6000 ppm), nonvolatile, relatively stable under acidic conditions, and is easily degraded under alkaline conditions. These properties are important determinants of its systemic action in plants and of its problematic environmental behavior. Possible environmental hazards involving the chemical include groundwater contamination and (more recently) excessive terminal residues in certain foods.<br />
DOI: 10.1289/ehp.94102s1123 PMCID: PMC1566767 PMID: 7737038 [Indexed for MEDLINE]<br />
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[3]. J Agromedicine. 2013;18(2):174-7. doi: 10.1080/1059924X.2013.766141.<br />
Aldicarb: a case series of watermelon-borne carbamate toxicity.<br />
D&#39;Haenens JP(1), McDonald KW, Langley RL, Higgins SA, Scott R, Farquhar PN, Meggs WJ.<br />
Author information: (1)Division of Toxicology, Department of Emergency Medicine, Brody School of Medicine at East Carolina University, Greenville, North Carolina 27858, USA.<br />
Improper use of pesticides on food plants can result in significant toxicity. In spite of regulations, enforcement, and prior episodes of poisonings, poisonings from misapplication of pesticides continues to occur. The objective of this study was to present a case series of toxicity resulting from ingestion of watermelon inappropriately treated with the carbamate insecticide aldicarb. A restrospective review of medical records, impounding the suspected watermelons, and chemical analysis of the watermelon samples using liquid chromatography and mass spectroscopy were carried out. Seven farm workers shared a watermelon and presented to a rural emergency department with symptoms of cholinergic poisoning. They were treated empirically with atropine and pralidoxime. The farmer denied use of insecticides other than rat poison on the watermelon patch. Chemical analyst verified aldicarb in the watermelon samples from the field, but none in control samples. Despite government regulations, application of restricted pesticides such as aldicarb continues to occur and cause significant poisonings.<br />
DOI: 10.1080/1059924X.2013.766141 PMID: 23540307 [Indexed for MEDLINE]<br />
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[4]. Arch Intern Med. 1994 Jan 24;154(2):221-4. doi: 10.1001/archinte.154.2.221.<br />
Aldicarb poisoning. A case report with prolonged cholinesterase inhibition and improvement after pralidoxime therapy.<br />
Burgess JL(1), Bernstein JN, Hurlbut K.<br />
Author information: (1)Section of Emergency Medicine, University of Arizona Health Sciences Center, Tucson.<br />
Aldicarb is the most potent of the commercially available carbamate pesticides and is an unusual source of acute human poisonings. We present the case of a 43-year-old man exposed to aldicarb who developed severe cholinergic symptoms and progressive weakness requiring intubation for 5 days. Both his red blood cell cholinesterase and plasma pseudocholinesterase levels were depressed for a minimum of 44 hours. He demonstrated neuromuscular improvement concurrent with pralidoxime administration. The pertinent medical literature on aldicarb poisoning is reviewed.<br />
DOI: 10.1001/archinte.154.2.221 PMID: 8285817 [Indexed for MEDLINE]<br />
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[5]. Environ Health Perspect. 1987 Jun;72:267-81. doi: 10.1289/ehp.8772267.<br />
The toxicologic effects of the carbamate insecticide aldicarb in mammals: a review.<br />
Risher JF, Mink FL, Stara JF.<br />
Aldicarb, 2-methyl-2-(methylthio)propionaldehyde-O-methylcarbamoyloxime, is an oxime carbamate insecticide manufactured by the Union Carbide Corporation and sold under the trade name Temik. It is a soil-applied systemic pesticide used against certain insects, mites, and nematodes, and is applied below the soil surface for absorption by plant roots. It is generally applied to the soil in the form of 5, 10, or 15% granules, and soil moisture is essential for the release of the toxicant. Uptake by plants is rapid. Aldicarb is currently registered for use on cotton, sugar beets, sugar cane (Louisiana only), potatoes, sweet potatoes, peanuts, oranges, pecans (Southeast only), dry beans, soybeans, and ornamental plants. Home and garden use is not permitted. Discovery of aldicarb and its oxidative sulfoxide and sulfone metabolites in well or ground water in Florida, Wisconsin, and New York, and accidental poisonings from ingesting contaminated watermelons and cucumbers in the South and West have spurred interest and concern about this pesticide. The primary mechanism of toxic action of aldicarb is cholinesterase inhibition. However, unlike the relatively irreversible anticholinesterase activity of the organophosphate pesticides, the carbamylation process which produces the anti-AChE action is quickly reversible. Aldicarb is readily absorbed through both the gut and the skin, but is rapidly metabolized and excreted in the urine almost completely within 24 hr. Although it is acutely toxic to humans and laboratory animals, aldicarb is not known to be carcinogenic, teratogenic, conclusively mutagenic, or to produce other long-term adverse health effects. In cases of accidental poisoning, the cholinergic symptoms have generally subsided within 6 hr, with no side effects or complications.<br />
DOI: 10.1289/ehp.8772267 PMCID: PMC1474664 PMID: 3304999 [Indexed for MEDLINE]

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