Aminocarb
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| Names | |
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| Preferred IUPAC name
4-(Dimethylamino)-3-methylphenyl methylcarbamate | |
| Other names
4-Dimethylamino-3-methylphenyl,N-Methylcarbamate
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| Identifiers | |
3D model (JSmol)
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| 2808681 | |
| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.016.356 |
| EC Number |
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PubChemCID
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| RTECS number |
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| UNII | |
| UN number | 2811 |
CompTox Dashboard(EPA)
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| Properties | |
| C11H16N2O2 | |
| Molar mass | 208.261g·mol−1 |
| Appearance | White crystalline solid or tan crystals |
| Melting point | 95.0 °C (203.0 °F; 368.1 K) |
| Boiling point | 298 °C (568 °F; 571 K) |
| Soluble | |
| Solubilityin other solvents | Soluble in polar org solvents; moderately soluble in aromatic solvents |
| Vapor pressure | 1.88 X 10-6 mm Hg |
| 5.64 X 10-10 atm cu m/mole | |
| Hazards | |
| Occupational safety and health(OHS/OSH): | |
Main hazards
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Maybe highly toxic by ingestion, toxic by skin absorption |
| GHSlabelling: | |
 
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| Danger | |
| H301,H311,H400,H411[1] | |
| P264,P273,P280,P301+P310,P312 | |
| NFPA 704(fire diamond) | |
| Flash point | 181 °C (358 °F; 454 K) |
| Lethal doseor concentration (LD, LC): | |
LD50(median dose)
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Oral-rat-30 mg/kg and Dermal-rat-275 mg/kg |
| Safety data sheet(SDS) | [1] |
| Related compounds | |
Except where otherwise noted, data are given for materials in theirstandard state(at 25 °C [77 °F], 100 kPa).
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Animocarb(Matacil) is anorganicchemical compoundwith the molecular formulaC11H16N2O2.It has a colorless or whitecrystal-like appearance and is most commonly used as aninsecticide.[2]
History
[edit]Aminocarb has been extensively used in eastern Canada since 1976 in order to control thespruce budworm.The fate of this chemical in the ecosystem and detection of aminocarb was studied by the use of two-dimensionalthin-layer chromatography.The use of thin-layer chromatography helped isolate and identify themethyl amino,aminoandhydroxymethylanalogues from thein vitrometabolismof aminocarb byliverhomogenatesfrom humans and rats.[3]
Production and uses
[edit]Aminocarb is acarbamateinsecticidewidely used to protectcottonfields, crop fields, andforestsfrominsectinfestation. It helps in the control ofaphids,soil mollusks,lepidopterouslarvae,and other types of chewing insects. It is most commonly administered as anaerosol spray.[4][5]
Reactions
[edit]Aminocarb can be degraded through irradiation and hydrolysis.
Irradiation
[edit]Aminocarb can be broken down byshort-waveultraviolet radiation.[7]Irradiationis often carried out by ahigh pressurexenon-mercurylamp.[8]Irradiatingaminocarb inethyl alcoholandcyclohexenesolutionsinitially causes theoxidationof thedimethylamine moiety.[7][9]The process eventually leads to the formation of a4-dimethylamino-3-methyl phenolproduct.[9]
Hydrolysis
[edit]Aminocarb undergoeshydrolysisto4-dimethylamino-3-methylphenolin 25 °C purified water whenpHof the water is 6.4. 4-dimethylamino-3-methylphenol is then either directly or via2-methyl-1,4-dihydorquinoneconverted to2-methyl-1,4-benzoquinone.Ifmethylamineordiethylamineare present in the solution 2-methyl-1,4-benzoquinone will readily react.Monoepoxidesanddiepoxidesof 2-methyl-1,4-benzoquinone are formed.[6]
Biomedical effects
[edit]In an experiment where youngbrown bullheadwere exposed to aminocarb at lethal andsublethalconcentrations, their tissue distribution was examined and showed that the concentration ofresiduesin each tissue increased with the concentration of exposure of aminocarb. The liver and stomach/intestine had the highest amount of accumulation of residues.[10]
Aminocarb is also known as acholinesteraseinhibitor that hasnervous systemeffects causing convulsions andrespiratory failure.It can also be absorbed through the skin, causing long-term effects to thenervous systemandliver.[11]
References
[edit]- ^"Aminocarb safety and hazards".pubchem.ncbi.nlm.nih.gov.Retrieved2022-12-02.
- ^Montgomery, John Harold (1993)."Aminocarb".Agrochemicals Desk Reference: Environmental Data.CRC Press. pp.21–2.ISBN978-0-87371-738-0.
- ^Sundaram, K.M.S.; Szeto, S.Y.; Hindle, R. (1980). "Detection of aminocarb and its major metabolites by thin-layer chromatography".Journal of Chromatography A.194(1): 100–3.doi:10.1016/S0021-9673(00)81057-2.PMID7391210.
- ^Sundaram, Kanth M. S.; Sundaram, Alam (1987)."Role of Formulation Ingredients and Physical Properties on Droplet Size Spectra, Deposition, and Persistence of Aerially Sprayed Aminocrab and Mexacarbate in Forest Litter and Soil Samples".Pesticide Formulations and Application Systems.7(986): 139–51.ISBN978-0-8031-0970-4.
- ^Dikshith, T. S. S (2010)."Aminocarb (CAS No. 2032-59-9)".Handbook of Chemicals and Safety.CRC Press. p. 76.ISBN978-1-4398-2060-5.
- ^abAizawa, Hiroyasu (2001). "Carbamates".Metabolic Maps.pp.74–81.doi:10.1016/B978-012045605-5/50007-6.ISBN978-0-12-045605-5.
- ^abFAO plant production and protection papers.Food and Agriculture Organization of the United Nations. 1976.ISBN978-92-5-100922-2.[page needed]
- ^Kamrin, Michael A.; Montgomery, John H. (1999-10-28).Agrochemical and Pesticide Desk Reference on CD-ROM.CRC Press.ISBN978-0-8493-2179-5.
- ^abKamin, Michael A.; Montgomery, John H (1999-09-01).Agrochemical and Pesticide Desk Reference on CD-ROM: Crcnetbase.CRC Press.ISBN978-0-8493-2179-5.[page needed]
- ^Richardson, GM; Qadri, SU (1986). "Tissue distribution of14C-labeled residues of aminocarb in brown bullhead (Ictalurus nebulosusLe Sueur) following acute exposure ".Ecotoxicology and Environmental Safety.12(2): 180–6.Bibcode:1986EcoES..12..180R.doi:10.1016/0147-6513(86)90055-2.PMID3792270.
- ^"Aminocarb".U.S. National Library of Medicine. Archived fromthe originalon 2013-03-02.Retrieved2012-10-27.