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Fenitrothion

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Title: Fenitrothion  
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Subject: Insecticide, Ethoprop, Methidathion, Omethoate, Chlorethoxyfos
Collection: Anticholinesterases, Endocrine Disruptors, Nitrobenzenes, Organophosphate Insecticides, Phosphorothioates
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Fenitrothion

Fenitrothion
Names
IUPAC name
O,O-Dimethyl O-(3-methyl-4-nitrophenyl) phosphorothioate
Other names
• Dimethoxy-(3-methyl-4-nitrophenoxy)thioxophosphorane
O,O-Dimethyl O-4-nitro-m-tolyl phosphorothioate
Identifiers
 Y
ChEBI  Y
ChEMBL  Y
ChemSpider  Y
Jmol-3D images Image
KEGG  Y
PubChem
UNII  Y
Properties
C9H12NO5PS
Molar mass 277.23 g·mol−1
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 mmHg
38.0 mg/L
Solubility Readily soluble in dichloromethane, 2-propanol, toluene, hardly soluble in n-hexane.[1]
log P 3.30 (octanol/water)[2]
Hazards
Lethal dose or concentration (LD, LC):
LD50 (Median dose)
Rat, oral: 500 mg/kg[3]

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

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

Fenitrothion (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

  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.  
  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.  
  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.  
  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.  
  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.  

External links

  • Fenitrothion in the Pesticide Properties DataBase (PPDB)
  • Compendium of Pesticide Common Names (source of data)
  • Hazardous Substances Data Bank (source of data)
  • Inchem
  • Entox
  • Re-evaluation of Fenitrothion by the Pest Management Regulatory Agency of Canada
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