Carbaryl

Base Information

• Chemical Name: Carbaryl
• CAS No.: 63-25-2
• Deprecated CAS: 11095-11-7,11130-47-5,51274-03-4,52001-89-5,1392204-77-1,1392204-77-1,51274-03-4,52001-89-5
• Molecular Formula: C12H11NO2
• Molecular Weight: 201.225
• Hs Code.: 29224999
• European Community (EC) Number: 200-555-0
• ICSC Number: 0121
• NSC Number: 27311
• UN Number: 2757
• UNII: R890C8J3N1
• DSSTox Substance ID: DTXSID9020247
• Nikkaji Number: J2.354J
• Wikipedia: Carbaryl
• Wikidata: Q415090
• NCI Thesaurus Code: C76389
• Metabolomics Workbench ID: 53038
• ChEMBL ID: CHEMBL46917
• Mol file: 63-25-2.mol

Synonyms:1-Naphthyl-N-methylcarbamate;Antigale;Carbaril;Carbaryl;Carbaryl, Manganese (2+) Salt;Carbaryl, Nickel (2+) Salt;Carbyl;Carylderm;Concentrat VO 18;Dog Net Insecticide Poudre;Dog-Net Insecticide Poudre;DogNet Insecticide Poudre;Fido's Free Itch;Fido's Free-Itch;Fido's FreeItch;G Wizz;G-Wizz;GWizz;insecticide Moureau, Poudre;insecticide Vetoquinol, Poudre;Joseph Lyddy;Lyddy, Joseph;Moureau, Poudre insecticide;Océcoxil;Poudre insecticide Moureau;Poudre insecticide Vetoquinol;Poutic;Sépou;Sevin;Skatta Tick Flea Louse Powder;Tigal;Vetoquinol, Poudre insecticide;VO 18, Concentrat

Chemical Property of Carbaryl

Chemical Property:

• Appearance/Colour: colourless solid
• Vapor Pressure: 1.83E-06mmHg at 25°C
• Melting Point: 142-146 °C(lit.)
• Refractive Index: 1.5300 (estimate)
• Boiling Point: 329.3 °C at 760 mmHg
• PKA: 12.02±0.46(Predicted)
• Flash Point: 153 °C
• PSA: 38.33000
• Density: 1.183 g/cm³
• LogP: 2.94890
• Storage Temp.: 0-6°C
• Solubility.: Moderately soluble in acetone, cyclohexanone, N,N-dimethylformamide (400–450 g/kg), and isophorone (Windholz et al., 1983; Worthing and Hance, 1991)
• Water Solubility.: Insoluble. 0.00826 g/100 mL
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 201.078978594
• Heavy Atom Count: 15
• Complexity: 230
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

Carbaryl ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, N, F
• Hazard Codes: Xn,N,F
• Statements: 22-40-50-67-65-50/53-38-11-20/22-20-43
• Safety Statements: 22-24-36/37-46-61-2-62-60-33-25-16-9

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Pesticides -> Carbamate Insecticides
• Canonical SMILES: CNC(=O)OC1=CC=CC2=CC=CC=C21
• Recent EU Clinical Trials: Clinical study phase III evaluating the efficacy of Diffusil H Forte spray
• Inhalation Risk: A harmful contamination of the air will not or will only very slowly be reached on evaporation of this substance at 20 °C; on spraying or dispersing, however, much faster.
• Effects of Short Term Exposure: The substance is irritating to the eyes and skin. The substance may cause effects on the nervous system. This may result in convulsions and respiratory depression. Cholinesterase inhibition. The effects may be delayed. Medical observation is indicated.
• Effects of Long Term Exposure: Cholinesterase inhibition. Cumulative effects are possible. See Acute Hazards/Symptoms. This substance is possibly carcinogenic to humans.
• Description: Carbaryl is a colourless to light tan or white or grey solid crystal depending on the purity of the compound. The crystals are essentially odourless and stable to heat, light, and acids but are not stable under alkaline conditions. It is non-corrosive to metals, packaging materials, and application equipment. Carbaryl is classified as a general use pesticide (GUP). It is sparingly soluble in water, but soluble in dimethylformamide, dimethyl sulfoxide, acetone, cyclohexanone, isopropanol, and xylene. Carbaryl is a wide-spectrum carbamate insecticide, which controls over 100 species of insects on citrus, fruit, cotton, forests, lawns, nuts, ornamentals, shade trees, and other crops, as well as on poultry, livestock, and pets. It is also used as a molluscicide and an acaricide. Carbaryl works whether it is ingested into the stomach of the pest or absorbed through direct contact. It is available as bait, dusts, wettable powders, granules, dispersions, and suspensions.
• Physical properties: White to light tan crystals with a bleach-like type odor. At 40 °C, the average odor threshold concentration and the lowest concentration at which an odor was detected were 280 and 37 μg/L, respectively. At 25 °C, the average taste threshold concentration and the lowest concentration at which a taste was detected were 140 and 44 μg/L, respectively (Young et al., 1996). White to light tan crystals with a bleach-like type odor. At 40°C, the average odor threshold concentration and the lowest concentration at which an odor was detected were 280 and 37 μg/L, respectively. At 25°C, the average taste threshold concentration and the lowest concentration at which a taste was detected were 140 and 44 μg/L, respectively (Young et al., 1996).
• Uses: Contact insecticide used to control most insects on fruits, vegetables and ornamentals Carbaryl is a pesticide, an insecticide of the carbamate group. It induced sensitization in a farmer. Contact insecticide. Cholinesterase inhibitor. Ectoparasiticide.
• Indications: Carbaryl (Sevin), a cholinesterase inhibitor insecticide, is used as a pediculicide in the form of a shampoo. This product has an objectionable odor, but has some ovicidal activity. It is an effective medication available in England and some other countries but not in the United States.

Technology Process of Carbaryl

There total 13 articles about Carbaryl which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.0%

methyl N-methylcarbamate (6642-30-4) + α-naphthol (90-15-3) → 1-naphthalenol methylcarbamate (63-25-2)

Guidance literature:

With trichlorophosphate; at 60 ℃; for 7h; Mechanism; analogous reaction of other carbamates;

DOI:10.1016/S0040-4020(01)86381-X

Reference yield: 80.0%

α-naphthol (90-15-3) + carbon dioxide (124-38-9,18923-20-1) + methylamine (74-89-5) → 1-naphthalenol methylcarbamate (63-25-2)

Guidance literature:

carbon dioxide; methylamine; With N-ethyl-N,N-diisopropylamine; In dichloromethane; at -40 ℃; for 0.75h;

α-naphthol; With trichlorophosphate; In dichloromethane;

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane;

Reference yield: 80.0%

N-methyl-thiocarbamic acid S-methyl ester (22013-97-4) + α-naphthol (90-15-3) → 1-naphthalenol methylcarbamate (63-25-2)

Guidance literature:

With triethylamine; In toluene; for 4h; Reflux;

DOI:10.1055/s-2008-1067233

upstream raw materials:

α-naphthol

methyl isocyanate

methyl N-methylcarbamate

N-methyl-thiocarbamic acid S-methyl ester

Downstream raw materials:

methylamine

α-naphthol

1-Naphthyl-N-hydroxymethyl-carbamat

[1,4]naphthoquinone

Refernces

• 1、 -. "METHOD OF CONVERTING CARBON DIOXIDE INTO CARBONYL COMPOUNDS". Page/Page column 16. . Retrieved 2019/05/02.
• 2、 Duspara, Petar A.,Islam, Md. Sadequl,Lough, Alan J.,Batey, Robert A.. "Synthesis and reactivity of N -alkyl carbamoylimidazoles: Development of N -methyl carbamoylimidazole as a methyl isocyanate equivalent". . p. 10362 - 10368. Retrieved 2013/01/15.