Carbofuran

Title: Carbofuran
CAS Registry Number: 1563-66-2
CAS Name: 2,3-Dihydro-2,2-dimethyl-7-benzofuranol methylcarbamate
Additional Names: methyl carbamic acid 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester; 2,2-dimethyl-2,3-dihydro-7-benzofuranyl-N-methylcarbamate; 2,2-dimethyl-7-coumaranyl N-methylcarbamate
Manufacturers' Codes: Bay 70143; NIA-10242
Trademarks: Furadan (FMC)
Molecular Formula: C12H15NO3
Molecular Weight: 221.25
Percent Composition: C 65.14%, H 6.83%, N 6.33%, O 21.69%
Literature References: Cholinesterase inhibitor. Prepn and use as insecticide: NL 6407316 (1964 to Bayer), C.A. 63, 583a (1965); NL 6500340; W. G. Scharpf, US 3474170; US 3474171 (1965, 1969, 1969 all to FMC); E. F. Orwoll, US 3356690 (1967 to FMC). Metabolism: H. W. Dorough, J. Agric. Food Chem. 16, 319 (1968); J. B. Knaak, ibid. 18, 832 (1970). Toxicity studies: J. S. Tobin, J. Occup. Med. 12, 16 (1970); M. A. Fahmy et al., J. Agric. Food Chem. 18, 793 (1970). Teratogenicity study: K. D. Courtney et al., J. Environ. Sci. Health B20, 373 (1985).
Properties: White crystalline solid, mp 150-153°. Soly in water at 25°: 700 ppm. Unstable in alk. LD50 orally in mice: 2 mg/kg (Fahmy, 1970).
Melting point: mp 150-153°
Toxicity data: LD50 orally in mice: 2 mg/kg (Fahmy, 1970)
CAUTION: Potential symptoms of overexposure are miosis, blurred vision; sweating, salivation, abdominal cramps, diarrhea, headache, nausea, vomiting, weakness; muscle twitching, incoordination, convulsions. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 52; Clinical Toxicology of Commercial Products, R. E. Gosselin et al., Eds. (Williams & Wilkins, Baltimore, 5th ed., 1984) Section II, p 305.
Use: Systemic insecticide, acaricide, nematocide.
Carbohydrazide Carbomycin Carbon Diselenide Carbon Disulfide Carbon Monoxide

Carbofuran
Carbofuran Carbofuran
Identifiers
CAS number 1563-66-2 YesY
PubChem 2566
ChemSpider 2468 YesY
UNII SKF77S6Y67 YesY
KEGG C14291 YesY
ChEBI CHEBI:34611 YesY
ChEMBL CHEMBL416081 YesY
Jmol-3D images Image 1
Properties
Molecular formula C12H15NO3
Molar mass 221.25 g mol−1
Appearance White, crystalline solid
Density 1.18 g/cm3
Melting point 151 °C; 304 °F; 424 K ([4])
Boiling point 313.3 °C; 595.9 °F; 586.5 K
Solubility in water 320 mg/L[1]
Solubility Highly soluble in N-methyl-2-pyrrolidone, dimethylformamide, dimethyl sulfoxide, acetone, acetonitrile, methylene chloride, cyclohexanone, benzene, and xylene[2]
log P 2.32 (octanol/water)[3]
Hazards
Flash point 143.3 °C; 289.9 °F; 416.4 K
LD50 8–14 mg/kg (oral, rat)
19 mg/kg (oral, dog)
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Carbofuran is one of the most toxic carbamate pesticides. It is marketed under the trade names Furadan, by FMC Corporation and Curater, among several others. It is used to control insects in 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 here the plant distributes it throughout its organs where insecticidal concentrations are attained. Carbofuran also has contact activity against pests.

Carbofuran usage has increased in recent years because it is one of the few insecticides effective on soybean aphids, which have expanded their range since 2002 to include most soybean-growing regions of the U.S. The main global producer is the FMC Corporation.