Carbofuran

Carbofuran
Carbofuran
Carbofuran
Carbofuran
Carbofuran
Names
Preferred IUPAC name
2,2-Dimethyl-2,3-dihydro-1-benzofuran-7-yl methylcarbamate
Other names
Furadan, Curater, Furacarb
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.014.867 Edit this at Wikidata
KEGG
UNII
  • 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) checkY
    Key: DUEPRVBVGDRKAG-UHFFFAOYSA-N checkY
  • CNC(=O)Oc1cccc2c1OC(C)C2
Properties
C12H15NO3
Molar mass 221.256 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)
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)
Lethal dose or concentration (LD, LC):
8–14 mg/kg (oral, rat)
19 mg/kg (oral, dog)
NIOSH (US health exposure limits):
PEL (Permissible)
 none[5]
REL (Recommended)
 TWA 0.1 mg/m3[5]
IDLH (Immediate danger)
 N.D.[5]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

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.

It is marketed under the trade names Furadan, by FMC Corporation and Curaterr 10 GR, by Bayer among several others.[6]

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 United States 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.[7]

  1. ^ Sharom MS, Miles JRW, Harris CR, McEwen FL (1980). "Behaviour of 12 Insecticides in soil and aqueous suspensions of soil and sediment". Water Res. 14 (8): 1095–1100. Bibcode:1980WatRe..14.1095S. doi:10.1016/0043-1354(80)90158-X.
  2. ^ US EPA/OPPTS; Reregistration Eligibility Decisions (REDs) Database on Carbofuran (1563-66-2). EPA-738-R-06-031 August 2006.
  3. ^ Hansch, C.; Leo, A.; D. Hoekman (1995). Exploring QSAR – Hydrophobic, Electronic, and Steric Constants. Washington, DC: American Chemical Society. p. 101.
  4. ^ Lide, David R. (1998). Handbook of Chemistry and Physics (87 ed.). Boca Raton, Florida: CRC Press. pp. 3–94. ISBN 978-0-8493-0594-8.
  5. ^ a b c NIOSH Pocket Guide to Chemical Hazards. "#0101". National Institute for Occupational Safety and Health (NIOSH).
  6. ^ Ravichandra, N.G. (2018). Agrochemicals in Plant Disease Management. Scientific Publishers. p. 110. ISBN 978-93-87991-91-0. Retrieved September 22, 2020.
  7. ^ 40 C.F.R.: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities (PDF) (July 1, 2008 ed.), Government Printing Office, archived from the original (PDF) on February 25, 2012, retrieved October 29, 2011