Carbofuran

Names

IUPAC name

2,2-Dimethyl-2,3-dihydro-1-benzofuran-7-yl methylcarbamate

Other names

Furadan, Curater, Furacarb

Identifiers

CAS Number

1563-66-2^Y

3D model (Jmol)

CHEBI:34611^Y

ChEMBL416081^Y

2468^Y

C14291^Y

SKF77S6Y67^Y

InChI=1S/C12H15NO3/c1-12(2)7-8-5-4-6-9(10(8)16-12)15-11(14)13-3/h4-6H,7H2,1-3H3,(H,13,14)^Y

Key: DUEPRVBVGDRKAG-UHFFFAOYSA-N^Y
InChI=1/C12H15NO3/c1-12(2)7-8-5-4-6-9(10(8)16-12)15-11(14)13-3/h4-6H,7H2,1-3H3,(H,13,14)

Key: DUEPRVBVGDRKAG-UHFFFAOYAB

SMILES

O=C(Oc2cccc1c2OC(C1)(C)C)NC

Properties

Chemical formula

C₁₂H₁₅NO₃

Molar mass

221.26 g·mol⁻¹

Appearance

White, crystalline solid

Density

1.18 g/cm³

Melting point

151 °C (304 °F; 424 K)

Boiling point

313.3 °C (595.9 °F; 586.5 K)

Solubility in water

320 mg/L

Solubility

Highly soluble in N-methyl-2-pyrrolidone, dimethylformamide, dimethyl sulfoxide, acetone, acetonitrile, methylene chloride, cyclohexanone, benzene, and xylene

log P

2.32 (octanol/water)

Hazards

Flash point

143.3 °C (289.9 °F; 416.4 K)

Lethal dose or concentration (LD, LC):

LD₅₀ (median dose)

8–14 mg/kg (oral, rat)
19 mg/kg (oral, dog)

US health exposure limits (NIOSH):

PEL (Permissible)

none

REL (Recommended)

TWA 0.1 mg/m³

IDLH (Immediate danger)

N.D.

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

(what is ^YN ?)

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.

Carbofuran exhibits toxicity mediated by the same mechanism as that of the notorious V-series nerve agents and presents a risk to human health. 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 (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.

The technical or chemical name of carbofuran is 2,3-dihydro-2,2-dimethyl-7-benzofuranyl methylcarbamate and its CAS number is 1563-66-2. It is manufactured by the reaction of methyl isocyanate with 2,3-dihydro-2,2-dimethyl-7-hydroxybenzofuran.

Carbofuran is banned in Canada and the European Union.

In 2008, the United States Environmental Protection Agency (EPA) announced that it intends to ban carbofuran. In December of that year, FMC Corp., the sole US manufacturer of carbofuran, announced that it had voluntarily requested that the United States Environmental Protection Agency cancel all but six of the previously allowed uses of that chemical as a pesticide. With this change, carbofuran usage in the US would be allowed only on maize, potatoes, pumpkins, sunflowers, pine seedlings and spinach grown for seed. However, in May 2009 EPA cancelled all food tolerances, an action which amounts to a de facto ban on its use on all crops grown for human consumption.

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