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Aldicarb information


Aldicarb
Skeletal formula of aldicarb
Ball-and-stick model of aldicarb
Names
IUPAC name
2-Methyl-2-(methylthio)propanal O-(N-methylcarbamoyl)oxime
Other names
Temik
Identifiers
CAS Number
  • 116-06-3 checkY
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL91732 checkY
ChemSpider
  • 7844539 checkY
ECHA InfoCard 100.003.749 Edit this at Wikidata
EC Number
  • 204-123-2
KEGG
  • C11015 checkY
PubChem CID
  • 9570071
RTECS number
  • UE2275000
UNII
  • 8V071SH05P checkY
CompTox Dashboard (EPA)
  • DTXSID0039223 Edit this at Wikidata
InChI
  • InChI=1S/C7H14N2O2S/c1-7(2,12-4)5-9-11-6(10)8-3/h5H,1-4H3,(H,8,10)/b9-5+ checkY
    Key: QGLZXHRNAYXIBU-WEVVVXLNSA-N checkY
  • InChI=1/C7H14N2O2S/c1-7(2,12-4)5-9-11-6(10)8-3/h5H,1-4H3,(H,8,10)/b9-5+
    Key: QGLZXHRNAYXIBU-WEVVVXLNBS
SMILES
  • CNC(=O)O/N=C/C(C)(C)SC
Properties
Chemical formula
C7H14N2O2S
Molar mass 190.26 g·mol−1
Appearance colorless crystals
Odor faint sulfur odor
Density 1.195 g/cm2
Melting point 99.5 °C (211.1 °F; 372.6 K)
Boiling point 251 °C (484 °F; 524 K)
Solubility in water
0.573 g/100 mL
Solubility soluble in acetone, benzene, chlorobenzene, diethyl ether, isopropyl alcohol, methylene chloride, toluene
slightly soluble in xylene
Hazards
Lethal dose or concentration (LD, LC):
LD50 (median dose)
0.84 mg/kg (oral, rats)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

Aldicarb is a carbamate insecticide which is the active substance in the pesticide Temik. It is effective against thrips, aphids, spider mites, lygus, fleahoppers, and leafminers, but is primarily used as a nematicide.[2] Aldicarb is a cholinesterase inhibitor which prevents the breakdown of acetylcholine in the synapse. Aldicarb is considered "extremely hazardous" by the EPA and World Health Organization and has been banned in more than 100 countries.[3] In case of severe poisoning, the victim dies of respiratory failure.

Aldicarb was first synthesized in 1965 by Payne and Weiden, and was sold on the market for the first time in 1970.[4] The synthesis of aldicarb results in both the E and Z isomers.[5]

Aldicarb is effective where resistance to organophosphate insecticides has developed, and is extremely important in potato production, where it is used for the control of soil-borne nematodes and some foliar pests. Its high level of solubility restricts its use in certain areas where the water table is close to the surface.

  1. ^ Kök, Fatma N; Arıca, M Yakup; Gencer, Oktay; Abak, Kazım; Hasırcı, Vasıf (1999). "Controlled release of aldicarb from carboxymethyl cellulose microspheres: in vitro and field applications". Pesticide Science. 55 (12): 1194–1202. doi:10.1002/(sici)1096-9063(199912)55:12<1194::aid-ps79>3.0.co;2-h.
  2. ^ "Temik". www.bayercropscienceus.us. Retrieved 2011-04-01.
  3. ^ Hettinger, Johnathan (21 November 2023). "EPA considers approving fruit pesticide despite risks to children, records show". The Guardian. Retrieved 21 November 2023.
  4. ^ Payne, L. K. Jr.; Stansbury, H. A. Jr.; Weiden, M. H. J. (July 1, 1966). "Synthesis and Insecticidal Properties of Some Cholinergic Trisubstituted Acetaldehyde O-(Methylcarbamoyl)oximes". Journal of Agricultural and Food Chemistry. 14 (4): 356-365. doi:10.1021/jf60146a007. Retrieved November 7, 2021.
  5. ^ "PubChem - Aldicarb (CID: 9570071)". PubChem. National Library of Medicine. Retrieved November 7, 2021.

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Aldicarb

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Aldicarb is a carbamate insecticide which is the active substance in the pesticide Temik. It is effective against thrips, aphids, spider mites, lygus,...

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Nematicide

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high volatility or other properties promoting migration through the soil. Aldicarb (Temik), a carbamate insecticide marketed by Bayer CropScience, is an example...

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for respiratory and skin irritation. Union Carbide blamed the leak of aldicarb oxime (made from MIC but does not contain any MIC itself), the main ingredient...

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production of carbamate pesticides (such as carbaryl, carbofuran, methomyl, and aldicarb). It has also been used in the production of rubbers and adhesives. As...

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VX, Novichok agents). organophosphorus insecticides (e.g., parathion, aldicarb) nicotine poisoning can be thought of as a subset of cholinergic crisis...

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Butocarboxim

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isomer of aldicarb. Carbamate insecticide Aldicarb Aharonson, N; Muszkat, Lea; Klein, M (1985). "Residue analysis of butocarboxim and aldicarb applied in...

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C7H14N2O2S

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The molecular formula C7H14N2O2S may refer to: Aldicarb, a carbamate insecticide which is the active substance in the pesticide Temik Butocarboxim, a carbamate...

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toxicities to humans of any insecticide widely used on field crops (only aldicarb and parathion are more toxic). 1 ml (1/4 teaspoon) can be fatal to humans...

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chlorides are used to prepare a number of pesticides, e.g. carbofuran and aldicarb. Carbamoyl chlorides are prepared by the reaction of an amine with phosgene:...

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feature the carbamate ester functional group. Included in this group are aldicarb (Temik), carbofuran (Furadan), carbaryl (Sevin), ethienocarb, fenobucarb...

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