Dioxathion

Last updated
Dioxathion
Dioxathion.svg
Dioxathion 3D ball.png
Names
IUPAC name
S,S'-1,4-dioxane-2,3-diyl O,O,O',O'-tetraethyl bis(dithiophosphate)
Other names
phosphorodithoic acid; S,S’-1,4-Dioxane- 2,3-Diyl
0,0,0’,0’-Tetraethyl Ester; Navadel; Delnatex;
Delnav; Deltic; dioxane phosphate
p-Dioxane-2,3-diyl ethyl phosphorodithioate
2,3-p-Dioxanethiol-S,S-bis(O,O-diethyl phosphoro-dithioate)
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.001.007 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C12H26O6P2S4/c1-5-15-19(21,16-6-2)23-11-12(14-10-9-13-11)24-20(22,17-7-3)18-8-4/h11-12H,5-10H2,1-4H3 Yes check.svgY
    Key: VBKKVDGJXVOLNE-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C12H26O6P2S4/c1-5-15-19(21,16-6-2)23-11-12(14-10-9-13-11)24-20(22,17-7-3)18-8-4/h11-12H,5-10H2,1-4H3
    Key: VBKKVDGJXVOLNE-UHFFFAOYAS
  • S=P(SC1OCCOC1SP(=S)(OCC)OCC)(OCC)OCC
Properties
C 12 H 26 O 6 P 2 S 4
Molar mass 456.2 g/mol
AppearanceThick reddish-brown liquid/powder
Odor garlicky
Density 1.26 g/cm3
Melting point −20 °C (−4 °F; 253 K)
Insoluble
Hazards
Flash point noncombustible [1]
NIOSH (US health exposure limits):
PEL (Permissible)
none [1]
REL (Recommended)
TWA 0.2 mg/m3 [1]
IDLH (Immediate danger)
N.D. [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)
Infobox references

Dioxathion, systematically known as p-dioxane-2,3-diyl ethyl phosphorodithioate, is an organophosphate pesticide. It is used as an insecticide on livestock and as an acaricide on citrus fruits, deciduous fruits and nuts.

Contents

Uses

Under the trade name Delnav, it can be used to control insects and mites on apples, pears, quince, grapes, and walnuts, and finds use in the control of ticks, horn flies, lice and sheep keds in various livestock, either as a spray or as a dip. Under the trade name Deltic, it is a restricted use pesticide for exterior control of fleas, ticks and mites, in kennels, dog houses, yards, and other recreational areas.

Toxicity

Dioxathion is an Extremely Hazardous Substance, as defined by Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act, and is no longer allowed to be sold in the United States. However, it continues to see use in some other countries. It has been known to cause inhibition of the enzyme cholinesterase in rats, and it is recommended that people who have exposure to dioxathion regularly get their plasma and red blood cell cholinesterase levels assessed. Persons exposed to other chemicals which affect cholinesterase levels, e.g. other organophosphates or carbamates, may be at an increased risk. There are no known carcinogenic or reproductive effects, but long term exposure may result in nerve damage, poor motor coordination, and personality changes of anxiety, depression or irritability.

Short-term effects may include irritation to the eyes, pupil constriction and blurring of vision, abdominal cramps, laboured breathing, nausea, vomiting, diarrhoea, muscle cramps and excess salivation. These are mostly classic symptoms of organophosphate poisoning.

Dioxathion must be stored away from alkalis, iron, tin and strong acids. Contact can be avoided by using protective clothing and eyeware. If poisoning occurs, a physician may administer atropine sulfate, or pralidoxime in case of severe poisoning.

Related Research Articles

Parathion Chemical compound

Parathion, also called parathion-ethyl or diethyl parathion and locally known as "Folidol", is an organophosphate insecticide and acaricide. It was originally developed by IG Farben in the 1940s. It is highly toxic to non-target organisms, including humans, so its use has been banned or restricted in most countries. The basic structure is shared by parathion methyl.

Malathion Chemical compound

Malathion is an organophosphate insecticide which acts as an acetylcholinesterase inhibitor. In the USSR, it was known as carbophos, in New Zealand and Australia as maldison and in South Africa as mercaptothion.

Chlorfenvinphos Chemical compound

Chlorfenvinphos is the common name of an organophosphorus compound that was widely used as an insecticide and an acaricide. The molecule itself can be described as an enol ester derived from dichloroacetophenone and diethylphosphonic acid. Chlorfenvinphos has been included in many products since its first use in 1963. However, because of its toxic effect as a cholinesterase inhibitor it has been banned in several countries, including the United States and the European Union. Its use in the United States was cancelled in 1991.

Ethion Chemical compound

Ethion (C9H22O4P2S4) is an organophosphate insecticide. Ethion is known to affect a neural enzyme called acetylcholinesterase and prevent it from working.

Diazinon Chemical compound

Diazinon, a colorless to dark brown liquid, is a thiophosphoric acid ester developed in 1952 by Ciba-Geigy, a Swiss chemical company. It is a nonsystemic organophosphate insecticide formerly used to control cockroaches, silverfish, ants, and fleas in residential, non-food buildings. Diazinon was heavily used during the 1970s and early 1980s for general-purpose gardening use and indoor pest control. A bait form was used to control scavenger wasps in the western U.S. Diazinon is used in flea collars for domestic pets in Australia and New Zealand. Residential uses of diazinon were outlawed in the U.S. in 2004 because of human health risks but it is still approved for agricultural uses. An emergency antidote is atropine.

Demeton-S-methyl is an organic compound with the molecular formula C6H15O3PS2. It was used as an organothiophosphate acaricide and organothiophosphate insecticide. It is flammable. With prolonged storage, Demeton-S-methyl becomes more toxic due to formation of a sulfonium derivative which has greater affinity to the human form of the acetylcholinesterase enzyme, and this may present a hazard in agricultural use.

Temefos Chemical compound

Temefos or temephos is an organophosphate larvicide used to treat water infested with disease-carrying insects including mosquitoes, midges, and black fly larvae.

Fenthion Chemical compound

Fenthion is an organothiophosphate insecticide, avicide, and acaricide. Like most other organophosphates, its mode of action is via cholinesterase inhibition. Due to its relatively low toxicity towards humans and mammals, fenthion is listed as moderately toxic compound in U.S. Environmental Protection Agency and World Health Organization toxicity class.

Methoxychlor Synthetic organochloride insecticide, now obsolete.

Methoxychlor is a synthetic organochloride insecticide, now obsolete.

Azinphos-methyl Chemical compound

Azinphos-methyl (Guthion) is a broad spectrum organophosphate insecticide manufactured by Bayer CropScience, Gowan Co., and Makhteshim Agan. Like other pesticides in this class, it owes its insecticidal properties to the fact that it is an acetylcholinesterase inhibitor. It is classified as an extremely hazardous substance in the United States as defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act, and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.

Dichlorvos

Dichlorvos is an organophosphate widely used as an insecticide to control household pests, in public health, and protecting stored products from insects. The compound has been commercially available since 1961 and has become controversial because of its prevalence in urban waterways and the fact that its toxicity extends well beyond insects. The insecticide has been banned in EU since 1998.

Phosmet Organophosphate non-systemic insecticide

Phosmet is a phthalimide-derived, non-systemic, organophosphate insecticide used on plants and animals. It is mainly used on apple trees for control of codling moth, though it is also used on a wide range of fruit crops, ornamentals, and vines for the control of aphids, suckers, mites, and fruit flies.

A recommended exposure limit (REL) is an occupational exposure limit that has been recommended by the United States National Institute for Occupational Safety and Health. The REL is a level that NIOSH believes would be protective of worker safety and health over a working lifetime if used in combination with engineering and work practice controls, exposure and medical monitoring, posting and labeling of hazards, worker training and personal protective equipment. To formulate these recommendations, NIOSH evaluates all known and available medical, biological, engineering, chemical, trade, and other information. Although not legally enforceable limits, RELS are transmitted to the Occupational Safety and Health Administration (OSHA) or the Mine Safety and Health Administration (MSHA) of the U.S. Department of Labor for use in promulgating legal standards.

Disulfoton Chemical compound

Disulfoton is an organophosphate acetylcholinesterase inhibitor used as an insecticide. It is manufactured under the name Di-Syston by Bayer CropScience. Disulfoton in its pure form is a colorless oil but the technical product used in vegetable fields is dark and yellowish with a sulfur odor. Disulfoton is processed as a liquid into carrier granules, these granules are mixed with fertilizer and clay to be made into a spike, designed to be driven into the ground. The pesticide is absorbed over time by the roots and translocated to all parts of the plant. The pesticide acts as a cholinesterase inhibitor and gives long lasting control.

Demeton Chemical compound

Demeton, sold as an amber oily liquid with a sulphur like odour under the name Systox™, is an organophosphate derivative causing irritability and shortness of breath to individuals repeatedly exposed. It was used as a phosphorothioate insecticide and acaricide and has the chemical formula C8H19O3PS2. Although it was previously used as an insecticide, it is now largely obsolete due to its relatively high toxicity to humans. Demeton consists of two components, demeton-S and demeton-O in a ratio of approximately 2:1 respectively. The chemical structure of demeton is closely related to military nerve agents such as VX and a derivative with one of the ethoxy groups replaced by methyl was investigated by both the US and Soviet chemical-weapons programs under the names V.sub.X and GD-7.

Naled Organophosphate insecticide

Naled (Dibrom) is an organophosphate insecticide. Its chemical name is dimethyl 1,2-dibromo-2,2-dichloroethylphosphate.

Carbophenothion Chemical compound

Carbophenothion also known as Stauffer R 1303 as for the manufacturer, Stauffer Chemical, is an organophosphorus chemical compound. It was used as a pesticide for citrus fruits under the name of Trithion. Carbophenothion was used as an insecticide and acaricide. Although not used anymore it is still a restricted use pesticide in the United States. The chemical is identified in the US as an extremely hazardous substance according to the Emergency Planning and Community Right-to-Know Act.

Tetraethyl pyrophosphate Chemical compound

Tetraethyl pyrophosphate, abbreviated TEPP, is an organophosphate compound with the formula [(C2H5O)2P(O)]2O. It is the tetraethyl derivative of pyrophosphate (P2O74-). It is a colorless oil that solidifies near room temperature. It is used as an insecticide. The compound hydrolyzes rapidly.

Sulfotep Chemical compound

Sulfotep (also known as tetraethyldithiopyrophosphate and TEDP) is a pesticide commonly used in greenhouses as a fumigant. The substance is also known as Dithione, Dithiophos, and many other names. Sulfotep has the molecular formula C8H20O5P2S2 and belongs to the organophosphate class of chemicals. It has a cholinergic effect, involving depression of the cholinesterase activity of the peripheral and central nervous system of insects. The transduction of signals is disturbed at the synapses that make use of acetylcholine. Sulfotep is a mobile oil that is pale yellow-colored and smells like garlic. It is primarily used as an insecticide.

Parathion methyl Chemical compound

Parathion methyl, or methyl parathion, is an organophosphate insecticide, possessing an organothiophosphate group. It is structurally very similar to parathion-ethyl. It is not allowed for sale and import in nearly all countries around the world, while a few allow it under subject to specified conditions only.

References

  1. 1 2 3 4 NIOSH Pocket Guide to Chemical Hazards. "#0238". National Institute for Occupational Safety and Health (NIOSH).