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
CAS Number	122-14-5 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:34757 Y
ChEMBL	ChEMBL347698 Y
ChemSpider	28941 Y
ECHA InfoCard	100.004.114
KEGG	C14442 Y
PubChem	31200
UNII	W8M4X3Y7ZY Y
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
SMILES S=P(Oc1cc(c(cc1)[N+]([O-])=O)C)(OC)OC
Properties
Chemical formula	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
Solubility in water	38.0 mg/L
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 [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

Mouse (female), oral: 1416 mg/kg

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, 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).

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.