Aminocarb

Last updated
Aminocarb
Aminocarb.svg
Aminocarb 3d structure.png
Names
Preferred IUPAC name
4-(Dimethylamino)-3-methylphenyl methylcarbamate
Other names
4-Dimethylamino-3-methylphenyl, N-Methylcarbamate
Identifiers
3D model (JSmol)
2808681
ChEBI
ChemSpider
ECHA InfoCard 100.016.356 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 217-990-7
PubChem CID
RTECS number
  • FC0175000
UNII
UN number 2811
  • InChI=1S/C11H16N2O2/c1-8-7-9(15-11(14)12-2)5-6-10(8)13(3)4/h5-7H,1-4H3,(H,12,14)
  • Cc1cc(ccc1N(C)C)N(C)C([O-])=O
Properties
C11H16N2O2
Molar mass 208.261 g·mol−1
AppearanceWhite 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
Solubility in other solventsSoluble 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
Maybe highly toxic by ingestion, toxic by skin absorption
GHS labelling:
GHS-pictogram-pollu.svg GHS-pictogram-skull.svg
Danger
H301, H311, H400, H411 [1]
P264, P273, P280, P301+P310, P312
NFPA 704 (fire diamond)
NFPA 704.svgHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Flash point 181 °C (358 °F; 454 K)
Lethal dose or concentration (LD, LC):
Oral-rat-30 mg/kg and Dermal-rat-275 mg/kg
Safety data sheet (SDS)
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Animocarb (Matacil) is an organic chemical compound with the molecular formula C 11 H 16 N 2 O 2. It has a colorless or white crystal-like appearance and is most commonly used as an insecticide. [2]

Contents

History

Aminocarb has been extensively used in eastern Canada since 1976 in order to control the spruce budworm. The fate of this chemical in the ecosystem and detection of aminocarb was studied by the use of two-dimensional thin-layer chromatography. The use of thin-layer chromatography helped isolate and identify the methyl amino, amino and hydroxymethyl analogues from the in vitro metabolism of aminocarb by liver homogenates from humans and rats. [3]

Production and uses

Aminocarb is a carbamate insecticide widely used to protect cotton fields, crop fields, and forests from insect infestation. It helps in the control of aphids, soil mollusks, lepidopterous larvae, and other types of chewing insects. It is most commonly administered as an aerosol spray. [4] [5]

Reactions

Aminocarb can be degraded through irradiation and hydrolysis.

Hydrolysis of aminocarb Hydrolysis of aminocarb.png
Hydrolysis of aminocarb

Irradiation

Aminocarb can be broken down by short-wave ultraviolet radiation. [7] Irradiation is often carried out by a high pressure xenon-mercury lamp. [8] Irradiating aminocarb in ethyl alcohol and cyclohexene solutions initially causes the oxidation of the dimethylamine moiety. [7] [9] The process eventually leads to the formation of a 4-dimethylamino-3-methyl phenol product. [9]

Hydrolysis

Aminocarb undergoes hydrolysis to 4-dimethylamino-3-methylphenol in 25 °C purified water when pH of the water is 6.4. 4-dimethylamino-3-methylphenol is then either directly or via 2-methyl-1,4-dihydorquinone converted to 2-methyl-1,4-benzoquinone. If methylamine or diethylamine are present in the solution 2-methyl-1,4-benzoquinone will readily react. Monoepoxides and diepoxides of 2-methyl-1,4-benzoquinone are formed. [6]

Biomedical effects

In an experiment where young brown bullhead were exposed to aminocarb at lethal and sublethal concentrations, their tissue distribution was examined and showed that the concentration of residues in 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 a cholinesterase inhibitor that has nervous system effects causing convulsions and respiratory failure. It can also be absorbed through the skin, causing long-term effects to the nervous system and liver. [11]

Related Research Articles

<span class="mw-page-title-main">Carbofuran</span> Toxic carbamate pesticide

Carbofuran is a carbamate pesticide, widely used around the world to control insects on a wide variety of field crops, including potatoes, corn and soybeans. It is a systemic insecticide, which means that the plant absorbs it through the roots, and from there the plant distributes it throughout its organs where insecticidal concentrations are attained. Carbofuran also has contact activity against pests. It is one of the most toxic pesticides still in use.

<span class="mw-page-title-main">Carbaryl</span> Chemical compound

Carbaryl is a chemical in the carbamate family used chiefly as an insecticide. It is a white crystalline solid previously sold under the brand name Sevin, which was a trademark of the Bayer Company. The Sevin trademark has since been acquired by GardenTech, which has eliminated carbaryl from most Sevin formulations. Union Carbide discovered carbaryl and introduced it commercially in 1958. Bayer purchased Aventis CropScience in 2002, a company that included Union Carbide pesticide operations. Carbaryl was the third-most-used insecticide in the United States for home gardens, commercial agriculture, and forestry and rangeland protection. As a veterinary drug, it is known as carbaril (INN).

<span class="mw-page-title-main">Dicofol</span> Chemical compound

Dicofol is an insecticide, an organochlorine that is chemically related to DDT. Dicofol is a miticide that is very effective against spider mite. Its production and use is banned internationally under the Stockholm Convention.

<span class="mw-page-title-main">Diazinon</span> Chemical compound

Diazinon, a colorless to dark brown liquid, is a thiophosphoric acid ester developed in 1952 by Ciba-Geigy, a Swiss chemical company. It is a nonsystemic organophosphate insecticide formerly used to control cockroaches, silverfish, ants, and fleas in residential, non-food buildings. Diazinon was heavily used during the 1970s and early 1980s for general-purpose gardening use and indoor pest control. A bait form was used to control scavenger wasps in the western U.S. Diazinon is used in flea collars for domestic pets in Australia and New Zealand. Diazinon is a major component in the "Golden Fleece" brand sheep dip. Residential uses of diazinon were outlawed in the U.S. in 2004 because of human health risks but it is still approved for agricultural uses. An emergency antidote is atropine.

<span class="mw-page-title-main">Aldicarb</span> Chemical compound (insecticide)

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. 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. In case of severe poisoning, the victim dies of respiratory failure.

<span class="mw-page-title-main">Azinphos-methyl</span> Chemical compound

Azinphos-methyl (Guthion) is a broad spectrum organophosphate insecticide manufactured by Bayer CropScience, Gowan Co., and Makhteshim Agan. Like other pesticides in this class, it owes its insecticidal properties to the fact that it is an acetylcholinesterase inhibitor. It is classified as an extremely hazardous substance in the United States as defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act, and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.

<span class="mw-page-title-main">Phosmet</span> Organophosphate non-systemic insecticide

Phosmet is a phthalimide-derived, non-systemic, organophosphate insecticide used on plants and animals. It is mainly used on apple trees for control of codling moth, though it is also used on a wide range of fruit crops, ornamentals, and vines for the control of aphids, suckers, mites, and fruit flies.

Carbamic acid, which might also be called aminoformic acid or aminocarboxylic acid, is the chemical compound with the formula H2NCOOH. It can be obtained by the reaction of ammonia NH3 and carbon dioxide CO2 at very low temperatures, which also yields ammonium carbamate [NH4]+[NH2CO2]. The compound is stable only up to about 250 K (−23 °C); at higher temperatures it decomposes into those two gases. The solid apparently consists of dimers, with the two molecules connected by hydrogen bonds between the two carboxyl groups –COOH.

Acibenzolar-<i>S</i>-methyl Chemical compound

Acibenzolar-S-methyl is the ISO common name for an organic compound that is used as a fungicide. Unusually, it is not directly toxic to fungi but works by inducing systemic acquired resistance, the natural defence system of plants.

The Bergmann degradation is a series of chemical reactions designed to remove a single amino acid from the carboxylic acid (C-terminal) end of a peptide. First demonstrated by Max Bergmann in 1934, it is a rarely used method for sequencing peptides. The later developed Edman degradation is an improvement upon the Bergmann degradation, instead cleaving the N-terminal amino acid of peptides to produce a hydantoin containing the desired amino acid.

<span class="mw-page-title-main">Dinoseb</span> Chemical compound used as a herbicide

Dinoseb is a common industry name for 6-sec-butyl-2,4-dinitrophenol, a herbicide in the dinitrophenol family. It is a crystalline orange solid which does not readily dissolve in water. Dinoseb is banned as an herbicide in the European Union (EU) and the United States because of its toxicity.

<span class="mw-page-title-main">Methiocarb</span> Chemical compound

Methiocarb is a carbamate pesticide which is used as an insecticide, bird repellent, acaricide and molluscicide since the 1960s. Methiocarb has contact and stomach action on mites and neurotoxic effects on molluscs. Seeds treated with methiocarb also affect birds. Other names for methiocarb are mesurol and mercaptodimethur.

<span class="mw-page-title-main">Chlorethoxyfos</span> Chemical compound

Chlorethoxyfos is an organophosphate acetylcholinesterase inhibitor used as an insecticide. It is registered for the control of corn rootworms, wireworms, cutworms, seed corn maggot, white grubs and symphylans on corn. The insecticide is sold under the trade name Fortress by E.I. du Pont de Nemours & Company.

<span class="mw-page-title-main">Hexachlorocyclopentadiene</span> Chemical compound

Hexachlorocyclopentadiene (HCCPD), also known as C-56, Graphlox, and HRS 1655, is an organochlorine compound with the formula C5Cl6. It is a precursor to pesticides, flame retardants, and dyes. It is a colourless liquid, although commercial samples appear lemon-yellow liquid sometimes with a bluish vapour. Many of its derivatives proved to be highly controversial, as studies showed them to be persistent organic pollutants. An estimated 270,000 tons were produced until 1976, and smaller amounts continue to be produced today. Two prominent manufacturers are Velsicol Chemical Corporation in the US and by Jiangsu Anpon Electrochemicals Co. in China.

<span class="mw-page-title-main">Tetraethyl pyrophosphate</span> Chemical compound

Tetraethyl pyrophosphate, abbreviated TEPP, is an organophosphate compound with the formula [(C2H5O)2P(O)]2O. It is the tetraethyl derivative of pyrophosphate (P2O74-). It is a colorless oil that solidifies near room temperature. It is used as an insecticide. The compound hydrolyzes rapidly.

<span class="mw-page-title-main">Sulfotep</span> Chemical compound

Sulfotep (also known as tetraethyldithiopyrophosphate and TEDP) is a pesticide commonly used in greenhouses as a fumigant. The substance is also known as Dithione, Dithiophos, and many other names. Sulfotep has the molecular formula C8H20O5P2S2 and belongs to the organophosphate class of chemicals. It has a cholinergic effect, involving depression of the cholinesterase activity of the peripheral and central nervous system of insects. The transduction of signals is disturbed at the synapses that make use of acetylcholine. Sulfotep is a mobile oil that is pale yellow-colored and smells like garlic. It is primarily used as an insecticide.

<span class="mw-page-title-main">Terbufos</span> Chemical compound

Terbufos is a chemical compound used in insecticides and nematicides. It is part of the chemical family of organophosphates. It is a clear, colourless to pale yellow or reddish-brown liquid and sold commercially as granulate.

<span class="mw-page-title-main">Ethiofencarb</span> Chemical compound

Ethiofencarb is a carbamate insecticide which is useful in controlling aphids on hard and soft fruits and some vegetables. It is not as dangerous as organophosphorous pesticides, but is considered highly toxic to humans in the UK, moderately toxic under US EPA classification, and highly toxic to aquatic life.

Pesticide degradation is the process by which a pesticide is transformed into a benign substance that is environmentally compatible with the site to which it was applied. Globally, an estimated 1 to 2.5 million tons of active pesticide ingredients are used each year, mainly in agriculture. Forty percent are herbicides, followed by insecticides and fungicides. Since their initial development in the 1940s, multiple chemical pesticides with different uses and modes of action have been employed. Pesticides are applied over large areas in agriculture and urban settings. Pesticide use, therefore, represents an important source of diffuse chemical environmental inputs.

<span class="mw-page-title-main">Dimethylcarbamoyl chloride</span> Chemical compound

Dimethylcarbamoyl chloride (DMCC) is a reagent for transferring a dimethylcarbamoyl group to alcoholic or phenolic hydroxyl groups forming dimethyl carbamates, usually having pharmacological or pesticidal activities. Because of its high toxicity and its carcinogenic properties shown in animal experiments and presumably also in humans, dimethylcarbamoyl chloride can only be used under stringent safety precautions.

References

  1. "Aminocarb safety and hazards". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-12-02.
  2. Montgomery, John Harold (1993). "Aminocarb". Agrochemicals Desk Reference: Environmental Data. CRC Press. pp.  21–2. ISBN   978-0-87371-738-0.
  3. 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. PMID   7391210.
  4. 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. ISBN   978-0-8031-0970-4.
  5. Dikshith, T. S. S (2010). "Aminocarb (CAS No. 2032-59-9)". Handbook of Chemicals and Safety. CRC Press. p. 76. ISBN   978-1-4398-2060-5.
  6. 1 2 Aizawa, Hiroyasu (2001). "Carbamates". Metabolic Maps . pp.  74–81. doi:10.1016/B978-012045605-5/50007-6. ISBN   978-0-12-045605-5.
  7. 1 2 FAO plant production and protection papers. Food and Agriculture Organization of the United Nations. 1976. ISBN   9789251009222.[ page needed ]
  8. Kamrin, Michael A.; Montgomery, John H. (1999-10-28). Agrochemical and Pesticide Desk Reference on CD-ROM. CRC Press. ISBN   9780849321795.
  9. 1 2 Kamin, Michael A.; Montgomery, John H (1999-09-01). Agrochemical and Pesticide Desk Reference on CD-ROM: Crcnetbase. CRC Press. ISBN   9780849321795.[ page needed ]
  10. Richardson, GM; Qadri, SU (1986). "Tissue distribution of 14C-labeled residues of aminocarb in brown bullhead (Ictalurus nebulosus Le Sueur) following acute exposure". Ecotoxicology and Environmental Safety. 12 (2): 180–6. doi:10.1016/0147-6513(86)90055-2. PMID   3792270.
  11. "Aminocarb". U.S. National Library of Medicine.