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Revision as of 21:51, 8 August 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,084 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEBI').← Previous edit Revision as of 16:06, 24 September 2011 edit undo128.237.238.186 (talk) Chonic -> chronic; un-emboldened "unexpectedly"Next edit →
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|doi=10.1016/j.chemosphere.2008.04.054 |title=Fenitrothion, an organophosphate, affects running endurance but not aerobic capacity in fat-tailed dunnarts (Sminthopsis crassicaudata) |year=2008 |last1=Buttemer |first1=William A. |last2=Story |first2=Paul G. |last3=Fildes |first3=Karen J. |last4=Baudinette |first4=Russell V. |last5=Astheimer |first5=Lee B. |journal=Chemosphere |volume=72 |issue=9 |pmid=18547601}}</ref> and at acute dose levels it reduced the energy of birds.<ref>{{cite journal |pages=524–530 |doi=10.1016/j.chemosphere.2010.12.057 |title=Fipronil toxicity in northern bobwhite quail Colinus virginianus: Reduced feeding behaviour and sulfone metabolite formation |year=2011 |last1=Kitulagodage |first1=Malsha |last2=Isanhart |first2=John |last3=Buttemer |first3=William A. |last4=Hooper |first4=Michael J. |last5=Astheimer |first5=Lee B. |journal=Chemosphere |volume=83 |issue=4 |pmid=21227481}}</ref> |doi=10.1016/j.chemosphere.2008.04.054 |title=Fenitrothion, an organophosphate, affects running endurance but not aerobic capacity in fat-tailed dunnarts (Sminthopsis crassicaudata) |year=2008 |last1=Buttemer |first1=William A. |last2=Story |first2=Paul G. |last3=Fildes |first3=Karen J. |last4=Baudinette |first4=Russell V. |last5=Astheimer |first5=Lee B. |journal=Chemosphere |volume=72 |issue=9 |pmid=18547601}}</ref> and at acute dose levels it reduced the energy of birds.<ref>{{cite journal |pages=524–530 |doi=10.1016/j.chemosphere.2010.12.057 |title=Fipronil toxicity in northern bobwhite quail Colinus virginianus: Reduced feeding behaviour and sulfone metabolite formation |year=2011 |last1=Kitulagodage |first1=Malsha |last2=Isanhart |first2=John |last3=Buttemer |first3=William A. |last4=Hooper |first4=Michael J. |last5=Astheimer |first5=Lee B. |journal=Chemosphere |volume=83 |issue=4 |pmid=21227481}}</ref>


In chonic (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.<ref>{{cite journal |pages=112–120 |doi=10.1006/eesa.1996.0090 |title=Chronic Toxicity of Fenitrothion to an Algae (Nannochloris oculata), a Rotifer (Brachionus calyciflorus), and the Cladoceran (Daphnia magna) |year=1996 |last1=Ferrando |first1=M |journal=Ecotoxicology and Environmental Safety |volume=35 |issue=2 |pmid=8950533 |last2=Sancho |first2=E |last3=Andreu-Moliner |first3=E}}</ref> 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.<ref>{{cite journal |pages=112–120 |doi=10.1006/eesa.1996.0090 |title=Chronic Toxicity of Fenitrothion to an Algae (Nannochloris oculata), a Rotifer (Brachionus calyciflorus), and the Cladoceran (Daphnia magna) |year=1996 |last1=Ferrando |first1=M |journal=Ecotoxicology and Environmental Safety |volume=35 |issue=2 |pmid=8950533 |last2=Sancho |first2=E |last3=Andreu-Moliner |first3=E}}</ref>


Just half of fenitrothion's minimally effective dose altered the thyroid structure of a freshwater murrel (the snakehead fish).<ref>{{cite journal |pages=97–105 |doi=10.1016/0269-7491(88)90121-2 |title=Effect of safe concentrations of some pesticides on thyroid in the freshwater murrel, Channa punctatus: A histopathological study |year=1988 |last1=Saxena |first1=P |last2=Mani |first2=K |journal=Environmental Pollution |volume=55 |issue=2 |pmid=15092506}}</ref> Just half of fenitrothion's minimally effective dose altered the thyroid structure of a freshwater murrel (the snakehead fish).<ref>{{cite journal |pages=97–105 |doi=10.1016/0269-7491(88)90121-2 |title=Effect of safe concentrations of some pesticides on thyroid in the freshwater murrel, Channa punctatus: A histopathological study |year=1988 |last1=Saxena |first1=P |last2=Mani |first2=K |journal=Environmental Pollution |volume=55 |issue=2 |pmid=15092506}}</ref>

Revision as of 16:06, 24 September 2011

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
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.114 Edit this at Wikidata
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C9H12NO5PS/c1-7-6-8(4-5-9(7)10(11)12)15-16(17,13-2)14-3/h4-6H,1-3H3Key: ZNOLGFHPUIJIMJ-UHFFFAOYSA-N
  • InChI=1/C9H12NO5PS/c1-7-6-8(4-5-9(7)10(11)12)15-16(17,13-2)14-3/h4-6H,1-3H3Key: ZNOLGFHPUIJIMJ-UHFFFAOYAZ
SMILES
  • S=P(Oc1cc(c(cc1)()=O)C)(OC)OC
Properties
Chemical formula C9H12NO5PS
Molar mass 277.23 g/mol
Appearance Yellow-brown liquid
Density 1.3227 g/cm
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.
log P 3.30 (octanol/water)
Hazards
Lethal dose or concentration (LD, LC):
LD50 (median dose) Rat, oral 500 mg/kg

Mouse (female), oral 1416 mg/kg

Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkverify (what is  ?) Infobox references
Chemical compound

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, and at acute dose levels it reduced the energy of birds.

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.

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

References

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  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

Pest control: Insecticides
Carbamates
Inorganic compounds
Insect growth regulators
Neonicotinoids
Organochlorides
Organophosphorus
Pyrethroids
Diamides
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Metabolites
Biopesticides
Acetylcholine receptor modulators
Muscarinic acetylcholine receptor modulators
mAChRsTooltip Muscarinic acetylcholine receptors
Agonists
Antagonists
Precursors
(and prodrugs)
See also
Receptor/signaling modulators
Nicotinic acetylcholine receptor modulators
Acetylcholine metabolism/transport modulators
Nicotinic acetylcholine receptor modulators
nAChRsTooltip Nicotinic acetylcholine receptors
Agonists
(and PAMsTooltip positive allosteric modulators)
Antagonists
(and NAMsTooltip negative allosteric modulators)
Precursors
(and prodrugs)
See also
Receptor/signaling modulators
Muscarinic acetylcholine receptor modulators
Acetylcholine metabolism/transport modulators
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