Fenitrothion

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Fenitrothion
Fenitrothion-Molecule-3D-balls-by-AHRLS-2013.png
Fenitrothion Structural Formulae .V.1.svg
Identifiers
CAS number 122-14-5 YesY
PubChem 31200
ChemSpider 28941 YesY
UNII W8M4X3Y7ZY YesY
KEGG C14442 YesY
ChEBI CHEBI:34757 YesY
ChEMBL CHEMBL347698 YesY
Jmol-3D images Image 1
Properties
Molecular formula C9H12NO5PS
Molar mass 277.23 g/mol
Appearance Yellow-brown liquid
Density 1.3227 g/cm3
Melting point 3.4 °C (38.1 °F; 276.5 K)
Boiling point 118 °C (244 °F; 391 K) at 0.05 mm Hg
Solubility in water 38.0 mg/L at 25 °C
Solubility Readily soluble in dichloromethane, 2-propanol, toluene, hardly soluble in n-hexane.[1]
log P 3.30 (octanol/water)[2]
Hazards
LD50 Rat, oral 500 mg/kg[3]

Mouse (female), oral 1416 mg/kg[4]

Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
Infobox references

Fenitrothion (IUPAC name: O,O-Dimethyl O-(3-methyl-4-nitrophenyl) phosphorothioate) is a phosphorothioate (organophosphate) insecticide; cheap and widely used worldwide.

In experiments fenitrothion at sublethal doses affected the motor movement of marsupials,[5] and at acute dose levels it reduced the energy of birds.[6]

In chronic (low) dose tests, unexpectedly only the lowest concentration (0.011 microgram/liter) of fenitrothion depressed the growth of an algae, though all of the chronic dose levels used were toxic in other ways to the algae.[7]

Just half of fenitrothion's minimally effective dose altered the thyroid structure of a freshwater murrel (the snakehead fish).[8]

In an unusual demonstration of resistance to pesticides, 8% of insects in farm fields were found to carry a symbiotic gut microbe that can metabolize and detoxify fenitrothion; after in-vitro tests showed that the microbe significantly increased the survival of fenitrothion-treated insects.[9]

References[edit]

  1. ^ Farm Chemicals Handbook 1999. Willoughby, OH: Meister Publishing Co., 1999., p. C 177
  2. ^ Hansch, C., Leo, A., D. Hoekman. Exploring QSAR - Hydrophobic, Electronic, and Steric Constants. Washington, DC: American Chemical Society., 1995., p. 60
  3. ^ Kirk-Othmer Encyclopedia of Chemical Technology. 3rd ed., Volumes 1-26. New York, NY: John Wiley and Sons, 1978-1984., p. V13 440 (1981)
  4. ^ WHO; Environ Health Criteria 133: Fenitrothion p.70 (1992)
  5. ^ Buttemer, William A.; Story, Paul G.; Fildes, Karen J.; Baudinette, Russell V.; Astheimer, Lee B. (2008). "Fenitrothion, an organophosphate, affects running endurance but not aerobic capacity in fat-tailed dunnarts (Sminthopsis crassicaudata)". Chemosphere 72 (9): 1315–1320. doi:10.1016/j.chemosphere.2008.04.054. PMID 18547601. 
  6. ^ Kitulagodage, Malsha; Isanhart, John; Buttemer, William A.; Hooper, Michael J.; Astheimer, Lee B. (2011). "Fipronil toxicity in northern bobwhite quail Colinus virginianus: Reduced feeding behaviour and sulfone metabolite formation". Chemosphere 83 (4): 524–530. doi:10.1016/j.chemosphere.2010.12.057. PMID 21227481. 
  7. ^ Ferrando, M; Sancho, E; Andreu-Moliner, E (1996). "Chronic Toxicity of Fenitrothion to an Algae (Nannochloris oculata), a Rotifer (Brachionus calyciflorus), and the Cladoceran (Daphnia magna)". Ecotoxicology and Environmental Safety 35 (2): 112–120. doi:10.1006/eesa.1996.0090. PMID 8950533. 
  8. ^ Saxena, P; Mani, K (1988). "Effect of safe concentrations of some pesticides on thyroid in the freshwater murrel, Channa punctatus: A histopathological study". Environmental Pollution 55 (2): 97–105. doi:10.1016/0269-7491(88)90121-2. PMID 15092506. 
  9. ^ Kikuchi, Y.; Hayatsu, M.; Hosokawa, T.; Nagayama, A.; Tago, K.; Fukatsu, T. (2012). "Symbiont-mediated insecticide resistance". Proceedings of the National Academy of Sciences 109 (22): 8618. doi:10.1073/pnas.1200231109.  edit

External links[edit]