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| Names | |
|---|---|
| Preferred IUPAC name O,O-DimethylO-(3-methyl-4-nitrophenyl) phosphorothioate | |
| Other names • Dimethoxy-(3-methyl-4-nitrophenoxy)thioxophosphorane O,O-DimethylO-4-nitro-m-tolyl phosphorothioate | |
| Identifiers | |
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3D model (JSmol) | |
| ChEBI | |
| ChEMBL | |
| ChemSpider |
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| ECHA InfoCard | 100.004.114 |
| KEGG |
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| UNII | |
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| 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 inn-hexane.[1] |
| logP | 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 theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Fenitrothion (IUPAC name:O,O-dimethylO-(3-methyl-4-nitrophenyl) phosphorothioate) is aphosphorothioate (organophosphate)insecticide that is inexpensive and widely used worldwide. Trade names includeSumithion, a 94.2% solution of fenitrothion.[5]
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Fenitrothion at sublethal doses affected the motor movement of marsupials,[6] and at acute dose levels it reduced the energy of birds.[7]
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.[8]
Just half of fenitrothion's minimally effective dose altered the thyroid structure of a freshwater murrel (the snakehead fish).[9]
Cases of non-specificencephalopathy and fatty visceral changes (Reye's syndrome) in children living in the vicinity of fenitrothion-spraying operations invoked the research described latterly inScience,[10] and originally inThe Lancet:[11]
2-day-old mice were dosed topically for 11 days with fenitrothion, amongst other substances. After a further 2 days a sublethal dose ofencephalomyocarditis virus was injected subcutaneously in known titre. Mortality-rates in the 10-day period aftervirus injection 4-9% in fenitrothion groups, and 0% in corn-oil controls. Fatty changes were noted in liver and kidney in the insecticide-virus groups. The encephalopathy showed no specific central-nervous system lesion, but death followed a sequence of paralysis and convulsions. The possible role of exposure to combinations of insecticides in human viral susceptibility requires further attention.
Further study showed that the illness was caused not by fenitrothion itself, but combinations which included the surfactants and the solvent (with or without the pesticide) clearly showed that pretreatment with these chemicals markedly increased the viral lethality in the test mice.[12]
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.[13]
