Fenitrothion

Fenitrothion
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
CAS number	122-14-5 Y
PubChem	31200
ChemSpider	28941 Y
UNII	W8M4X3Y7ZY Y
KEGG	C14442 Y
ChEBI	CHEBI:34757 Y
ChEMBL	CHEMBL347698 Y
Jmol-3D images	Image 1
SMILES S=P(Oc1cc(c(cc1)[N+]([O-])=O)C)(OC)OC
InChI InChI=1S/C9H12NO5PS/c1-7-6-8(4-5-9(7)10(11)12)15-16(17,13-2)14-3/h4-6H,1-3H3 Y Key: ZNOLGFHPUIJIMJ-UHFFFAOYSA-N Y InChI=1/C9H12NO5PS/c1-7-6-8(4-5-9(7)10(11)12)15-16(17,13-2)14-3/h4-6H,1-3H3 Key: ZNOLGFHPUIJIMJ-UHFFFAOYAZ
Properties
Molecular formula	C9H12NO5PS
Molar mass	277.23 g/mol
Appearance	Yellow-brown liquid
Density	1.3227 g/cm3
Melting point	3.4 °C
Boiling point	118 °C 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]
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Fenitrothion (IUPAC name: O,O-Dimethyl O-(3-methyl-4-nitrophenyl) phosphorothioate) is a phosphorothioate (organophosphate) insecticide.

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]

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. 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. 

External links

• 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