Dimefox

Last updated
Dimefox
Dimefox-3D-balls-by-AHRLS-2012.png
Dimefox.svg
Names
IUPAC name
N-[dimethylamino(fluoro)phosphoryl]-N-methylmethanamine
Other names
TL-792 [1]
T-2002 [1]
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.003.706 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 204-076-8
KEGG
PubChem CID
UNII
  • InChI=1S/C4H12FN2OP/c1-6(2)9(5,8)7(3)4/h1-4H3 X mark.svgN
    Key: PGJBQBDNXAZHBP-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C4H12FN2OP/c1-6(2)9(5,8)7(3)4/h1-4H3
    Key: PGJBQBDNXAZHBP-UHFFFAOYAM
  • CN(C)P(=O)(N(C)C)F
Properties
C4H12FN2OP
Molar mass 154.125 g·mol−1
Appearancecolourless liquid
Density 1.11 g·mL–1
14.8 g·L–1
Vapor pressure 14663 mPa
2.28·10–8 atm·m3·mol–1 [2]
Pharmacology
inhalation and dermal contact
Legal status
  • UK:Banned
  • US:Banned
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Highly Toxic
GHS labelling:
GHS-pictogram-skull.svg
Danger
H300, H310
P262, P264, P270, P280, P301+P310, P302+P350, P310, P321, P322, P330, P361, P363, P405, P501
Lethal dose or concentration (LD, LC):
2 mg/kg (oral, mice) [1]
1 mg/kg (oral, rats) [1]
3 mg/kg (intravenous, rabbits) [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Dimefox, also known as TL-792 or T-2002, is a highly toxic organophosphate insecticide. In its pure form it is a colourless liquid with a fishy odour. [3] Dimefox was first produced in 1940 by the group of Gerhard Schrader in Germany. It was historically used as a pesticide, but has been deemed obsolete or discontinued for use by the World Health Organization due to being an inhibitor of acetylcholinesterase.[ citation needed ] It is not guaranteed that all commercial use of this compound ceased, but in most countries[ which? ] it is no longer registered for use as a pesticide. [4] It is considered an extremely hazardous substance as defined by the United States Emergency Planning and Community Right-to-Know Act.

See also

Related Research Articles

<span class="mw-page-title-main">Pesticide</span> Substance used to destroy pests

Pesticides are substances that are meant to control pests. This includes herbicide, insecticide, nematicide, molluscicide, piscicide, avicide, rodenticide, bactericide, insect repellent, animal repellent, microbicide, fungicide, and lampricide. The most common of these are herbicides, which account for approximately 50% of all pesticide use globally. Most pesticides are intended to serve as plant protection products, which in general, protect plants from weeds, fungi, or insects. As an example, the fungus Alternaria solani is used to combat the aquatic weed Salvinia.

<span class="mw-page-title-main">Herbicide</span> Chemical used to kill unwanted plants

Herbicides, also commonly known as weed killers, are substances used to control undesired plants, also known as weeds. Selective herbicides control specific weed species while leaving the desired crop relatively unharmed, while non-selective herbicides can be used to clear waste ground, industrial and construction sites, railways and railway embankments as they kill all plant material with which they come into contact. Apart from selective/non-selective, other important distinctions include persistence, means of uptake, and mechanism of action. Historically, products such as common salt and other metal salts were used as herbicides, however, these have gradually fallen out of favor, and in some countries, a number of these are banned due to their persistence in soil, and toxicity and groundwater contamination concerns. Herbicides have also been used in warfare and conflict.

<span class="mw-page-title-main">Malathion</span> 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.

<span class="mw-page-title-main">Chlorpyrifos</span> Chemical compound

Chlorpyrifos (CPS), also known as Chlorpyrifos ethyl, is an organophosphate pesticide that has been used on crops, animals, and buildings, and in other settings, to kill several pests, including insects and worms. It acts on the nervous systems of insects by inhibiting the acetylcholinesterase enzyme. Chlorpyrifos was patented in 1966 by Dow Chemical Company.

<span class="mw-page-title-main">Organophosphate</span> Organic compounds with the structure O=P(OR)3

In organic chemistry, organophosphates are a class of organophosphorus compounds with the general structure O=P(OR)3, a central phosphate molecule with alkyl or aromatic substituents. They can be considered as esters of phosphoric acid.

<span class="mw-page-title-main">Agrochemical</span> Any chemical used in agriculture

An agrochemical or agrichemical, a contraction of agricultural chemical, is a chemical product used in industrial agriculture. Agrichemical refers to biocides and synthetic fertilizers. It may also include hormones and other chemical growth agents.

Chloropicrin, also known as PS and nitrochloroform, is a chemical compound currently used as a broad-spectrum antimicrobial, fungicide, herbicide, insecticide, and nematicide. It was used as a poison gas in World War I. Its chemical structural formula is Cl3CNO2.

<span class="mw-page-title-main">Endosulfan</span> Chemical compound

Endosulfan is an off-patent organochlorine insecticide and acaricide that is being phased out globally. It became a highly controversial agrichemical due to its acute toxicity, potential for bioaccumulation, and role as an endocrine disruptor. Because of its threats to human health and the environment, a global ban on the manufacture and use of endosulfan was negotiated under the Stockholm Convention in April 2011. The ban has taken effect in mid-2012, with certain uses exempted for five additional years. More than 80 countries, including the European Union, Australia, New Zealand, several West African nations, the United States, Brazil, and Canada had already banned it or announced phase-outs by the time the Stockholm Convention ban was agreed upon. It is still used extensively in India and China despite laws against its use. It is also used in a few other countries. It is produced by the Israeli firm Makhteshim Agan and several manufacturers in India and China. On 13.05.2011, the India Supreme Court ordered a ban on the production and sale of endosulfan in India, pending further notice.

<span class="mw-page-title-main">Glufosinate</span> Broad-spectrum herbicide

Glufosinate is a naturally occurring broad-spectrum herbicide produced by several species of Streptomyces soil bacteria. Glufosinate is a non-selective, contact herbicide, with some systemic action. Plants may also metabolize bialaphos and phosalacine, other naturally occurring herbicides, directly into glufosinate. The compound irreversibly inhibits glutamine synthetase, an enzyme necessary for the production of glutamine and for ammonia detoxification, giving it antibacterial, antifungal and herbicidal properties. Application of glufosinate to plants leads to reduced glutamine and elevated ammonia levels in tissues, halting photosynthesis and resulting in plant death.

<span class="mw-page-title-main">Endrin</span> Chemical compound

Endrin is an organochloride with the chemical formula C12H8Cl6O that was first produced in 1950 by Shell and Velsicol Chemical Corporation. It was primarily used as an insecticide, as well as a rodenticide and piscicide. It is a colourless, odorless solid, although commercial samples are often off-white. Endrin was manufactured as an emulsifiable solution known commercially as Endrex. The compound became infamous as a persistent organic pollutant and for this reason it is banned in many countries.

Agricultural chemistry is the study of chemistry, especially organic chemistry and biochemistry, as the relate to agriculture. This includes agricultural production, the use of ammonia in fertilizer, pesticides, and how plant biochemistry can be used to genetically alter crops. Agricultural chemistry is not a distinct discipline, but a common thread that ties together genetics, physiology, microbiology, entomology, and numerous other sciences that impinge on agriculture.

In pharmacology and biochemistry, mode of action (MoA) describes a functional or anatomical change, resulting from the exposure of a living organism to a substance. In comparison, a mechanism of action (MOA) describes such changes at the molecular level.

<span class="mw-page-title-main">Tebuconazole</span> Chemical compound

Tebuconazole is a triazole fungicide used agriculturally to treat plant pathogenic fungi.

<span class="mw-page-title-main">Environmental impact of pesticides</span> Environmental effect

The environmental effects of pesticides describe the broad series of consequences of using pesticides. The unintended consequences of pesticides is one of the main drivers of the negative impact of modern industrial agriculture on the environment. Pesticides, because they are toxic chemicals meant to kill pest species, can affect non-target species, such as plants, animals and humans. Over 98% of sprayed insecticides and 95% of herbicides reach a destination other than their target species, because they are sprayed or spread across entire agricultural fields. Other agrochemicals, such as fertilizers, can also have negative effects on the environment.

<span class="mw-page-title-main">Clothianidin</span> Chemical compound

Clothianidin is an insecticide developed by Takeda Chemical Industries and Bayer AG. Similar to thiamethoxam and imidacloprid, it is a neonicotinoid. Neonicotinoids are a class of insecticides that are chemically similar to nicotine, which has been used as a pesticide since the late 1700s. Clothianidin and other neonicotinoids act on the central nervous system of insects as an agonist of nAChR, the same receptor as acetylcholine, the neurotransmitter that stimulates and activating post-synaptic acetylcholine receptors but not inhibiting AChE. Clothianidin and other neonicotinoids were developed to last longer than nicotine, which is more toxic and which breaks down too quickly in the environment. However, studies published in 2012 show that neonicotinoid dust released at planting time may persist in nearby fields for several years and be taken up into non-target plants, which are then foraged by bees, caterpillars, and other insects.

<span class="mw-page-title-main">Azinphos-ethyl</span> Chemical compound

Azinphos-ethyl was a broad-spectrum organophosphate insecticide.

<span class="mw-page-title-main">Thiamethoxam</span> Chemical compound

Thiamethoxam is the ISO common name for a mixture of cis-trans isomers used as a systemic insecticide of the neonicotinoid class. It has a broad spectrum of activity against many types of insects and can be used as a seed dressing.

<span class="mw-page-title-main">Carbophenothion</span> 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.

<span class="mw-page-title-main">Mexacarbate</span> Chemical compound

Mexacarbate is a carbamate pesticide developed by Alexander Shulgin and marketed in 1961 by Dow Chemical Company under the trade name Zectran. As of 2009, mexacarbate is considered obsolete or discontinued, according to the World Health Organization. It is notable for being the first biodegradable pesticide.

<span class="mw-page-title-main">Parathion methyl</span> 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 5 Chemical Warfare Agents, and Related Chemical Problems. Parts I-II.
  2. "Dimefox".
  3. "IUPAC FOOTPRINT Pesticides Properties Database". Archived from the original on 2011-07-22. Retrieved 2011-04-06.
  4. the WHO recommended classification of pesticides by hazard and guidelines to classification 2009,