Fenitrothion

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Fenitrothion
Fenitrothion Structural Formulae .V.1.svg
Fenitrothion-Molecule-3D-balls-by-AHRLS-2013.png
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
122-14-5 YesY
ChEBI CHEBI:34757 YesY
ChEMBL ChEMBL347698 YesY
ChemSpider 28941 YesY
Jmol 3D model Interactive image
KEGG C14442 YesY
PubChem 31200
UNII W8M4X3Y7ZY YesY
  • 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 YesY
    Key: ZNOLGFHPUIJIMJ-UHFFFAOYSA-N YesY
  • 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
  • S=P(Oc1cc(c(cc1)[N+]([O-])=O)C)(OC)OC
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]
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
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,[3] and at acute dose levels it reduced the energy of birds.[4]

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.[5]

Just half of fenitrothion's minimally effective dose altered the thyroid structure of a freshwater murrel (the snakehead fish).[6]

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.[7]

References

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External links

  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
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