Names | |
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IUPAC name 2,4,6,8-tetramethyl- | |
Other names metaldehyde metacetaldehyde ethanal tetramer | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.003.274 |
EC Number |
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KEGG | |
PubChem CID | |
UNII | |
UN number | 1332 |
CompTox Dashboard (EPA) | |
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Properties | |
C8H16O4 | |
Molar mass | 176.212 g/mol |
Density | 1.27 g/cm3 |
Melting point | 246 °C (475 °F; 519 K) |
Boiling point | sublimes at110 to 120 °C (230 to 248 °F; 383 to 393 K) |
Hazards | |
GHS labelling: [1] | |
Danger | |
H228, H301, H361f, H412 | |
P203, P210, P240, P241, P264, P270, P273, P280, P301+P316, P318, P321, P330, P370+P378, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Metaldehyde is an organic compound with the formula (C8H16O4). It is used as a pesticide against slugs and snails. [2] It is the cyclic tetramer of acetaldehyde. [3]
Metaldehyde is flammable, toxic if ingested in large quantities, and irritating to the skin and eyes. It has a white crystalline appearance with a menthol odor. [4]
Metaldehyde is obtained in moderate yields by treatment of acetaldehyde with various acid catalysts, such as hydrogen bromide, and cooling. The liquid trimer, paraldehyde is also obtained. The reaction is reversible; upon heating to about 80 °C, metaldehyde and paraldehyde revert to acetaldehyde.
Metaldehyde exists as a mixture of four stereoisomers, molecules that differ with respect to the relative orientation of the methyl groups on the 8-membered ring. The stereoisomers have respectively the molecular symmetries Cs (with symmetry of order 2), C2v (order 4), D2d (order 8), and C4v (order 8). All have at least one plane of reflexion, so none of them is chiral.
It is sold under various trade names as a molluscicide, including Antimilice, Ariotox, Blitzem (in Australia), Cekumeta, Deadline, Defender (in Australia), Halizan, Limacide, Limatox, Limeol, Meta, Metason, Mifaslug, Namekil, Slug Fest, and Slugit. Typically it is applied in pellet form, but it is also found as a liquid spray, granules, paste, or dust. Often the pesticide includes bran or molasses to attract pests, making it attractive to household pets as well. [5]
Metaldehyde is effective on pests by contact or ingestion and works by limiting the production of mucus in mollusks making them susceptible to dehydration. [6]
Metaldehyde products were used to control the invasive African land snail population in Miami-Dade County in Florida. Experimental use permits from the U.S. Environmental Protect Agency authorized the application amount and usage in residential areas. [6]
Due to the contamination of drinking water by metaldehyde's use in agriculture, a specialist organisation was established in 2008 called "The Metaldehyde Stewardship Group (MSG)".
On 19 December 2018, the British government banned the use of metaldehyde slug pellets outdoors from spring 2020; after this date it would only be legal to use it in permanent greenhouses. [7] In July 2019, the ban was overturned after the High Court in London agreed with a challenge to its legality. Metaldehyde pellets returned to the UK market until 18 September 2020, when the British government banned the use of metaldehyde slug pellets outdoors after 31 March 2022. [8]
Metaldehyde was originally developed as a solid fuel. [9] It is still used as a camping fuel, also for military purposes, or solid fuel in lamps. It may be purchased in a tablet form to be used in small stoves, and for preheating of Primus type stoves. It is sold under the trade name of "META" by Lonza Group of Switzerland; it can be included in the field ration of some nations.
Metaldehyde has a toxicity profile identical to that for acetaldehyde, being mildly toxic [10] and a respiratory irritant at the 50 ppm level. In terms of water safety, during periods of rainfall metaldehyde pellets become agitated and can seep into natural water courses. The European Commission restricts metaldehyde levels to 0.1 µg/L in drinking water. [11]
Metaldehyde-containing slug baits are banned in some countries as they are toxic to dogs and cats and disturb the natural ecosystems. [2] [12] There is no antidote or specific treatment plan for metaldehyde poisoning. Symptoms of poisoning in dogs and cats vary and are very similar to poisonings by other substances, however they can include tremors, drooling, hyperthermia, vomiting, and restlessness. If left untreated, symptoms will proceed to seizures and death within days. Severity of symptoms and speed of onset depend on the quantity ingested and the other contents of the stomach which affect absorption. [13]
A diagnosis can be made by an analysis of stomach contents, which tend to have an apple cider vinegar odor, as well as a history of exposure to the chemical. Treatment includes IV fluids, sedation, lowering body temperature, and purging of stomach contents with charcoal. Prompt and aggressive medical attention after a poisoning may make a full recovery possible within 2–3 days. [13]
Due to this toxicity, pet owners may want to investigate alternatives which are not as toxic to pets, such as ferric sodium EDTA or aluminium sulfate. [14] The metaldehyde tablets resemble candies and do not taste bad, making accidental ingestion possible by children or even by adults unaware of their true nature. Their use was popular during the interwar period and several cases of poisoning resulted. [15] Baits may contain a bitterant to prevent accidental consumption by pets or children.
Oral ingestion of metaldehyde have been described in adults attempting suicide. Amongst them, majority experienced gastrointestinal or neurological symptoms. When compared to humans with accidental ingestion of metaldehyde, those attempting suicide tended to be symptomatic, develop seizures, require care at the intensive care unit, and suffered longer hospitalizations. [16]
A poison is any chemical substance that is harmful or lethal to living organisms. The term is used in a wide range of scientific fields and industries, where it is often specifically defined. It may also be applied colloquially or figuratively, with a broad sense.
Acetaldehyde (IUPAC systematic name ethanal) is an organic chemical compound with the formula CH3 CHO, sometimes abbreviated as MeCHO. It is a colorless liquid or gas, boiling near room temperature. It is one of the most important aldehydes, occurring widely in nature and being produced on a large scale in industry. Acetaldehyde occurs naturally in coffee, bread, and ripe fruit, and is produced by plants. It is also produced by the partial oxidation of ethanol by the liver enzyme alcohol dehydrogenase and is a contributing cause of hangover after alcohol consumption. Pathways of exposure include air, water, land, or groundwater, as well as drink and smoke. Consumption of disulfiram inhibits acetaldehyde dehydrogenase, the enzyme responsible for the metabolism of acetaldehyde, thereby causing it to build up in the body.
Roach bait is a modern pest control used for the extermination of cockroaches at indoor locations. The effectiveness of this method of pest control exploits the cannibalistic and coprophagic tendencies of cockroaches.
Bait is any appetizing substance used to attract prey when hunting or fishing, most commonly in the form of trapping, ambushing and angling.
Molluscicides – also known as snail baits, snail pellets, or slug pellets – are pesticides against molluscs, which are usually used in agriculture or gardening, in order to control gastropod pests specifically slugs and snails which damage crops or other valued plants by feeding on them.
Chlorfenvinphos is 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.
Pest control is the regulation or management of a species defined as a pest; such as any animal, plant or fungus that impacts adversely on human activities or environment. The human response depends on the importance of the damage done and will range from tolerance, through deterrence and management, to attempts to completely eradicate the pest. Pest control measures may be performed as part of an integrated pest management strategy.
Rodenticides are chemicals made and sold for the purpose of killing rodents. While commonly referred to as "rat poison", rodenticides are also used to kill mice, woodchucks, chipmunks, porcupines, nutria, beavers, and voles. Despite the crucial roles that rodents play in nature, there are times when they need to be controlled.
Sodium fluoroacetate, also known as compound 1080, is an organofluorine chemical compound with the formula FCH2CO2Na. This colourless salt has a taste similar to that of table salt (sodium chloride) and is used as a rodenticide.
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. Diazinon is a major component in the "Golden Fleece" brand sheep dip. 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.
Aldicarb is a carbamate insecticide which is the active substance in the pesticide Temik. It is effective against thrips, aphids, spider mites, lygus, fleahoppers, and leafminers, but is primarily used as a nematicide. Aldicarb is a cholinesterase inhibitor which prevents the breakdown of acetylcholine in the synapse. Aldicarb is considered "extremely hazardous" by the EPA and World Health Organization and has been banned in more than 100 countries. In case of severe poisoning, the victim dies of respiratory failure.
Fipronil is a broad-spectrum insecticide that belongs to the phenylpyrazole chemical family. Fipronil disrupts the insect central nervous system by blocking the ligand-gated ion channel of the GABAA receptor and glutamate-gated chloride (GluCl) channels. This causes hyperexcitation of contaminated insects' nerves and muscles. Fipronil's specificity towards insects is believed to be due to its greater binding affinity for the GABAA receptors of insects than to those of mammals, and for its action on GluCl channels, which do not exist in mammals. As of 2017, there does not appear to be significant resistance among fleas to fipronil.
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.
Mirex is an organochloride that was commercialized as an insecticide and later banned because of its impact on the environment. This white crystalline odorless solid is a derivative of cyclopentadiene. It was popularized to control fire ants but by virtue of its chemical robustness and lipophilicity it was recognized as a bioaccumulative pollutant. The spread of the red imported fire ant was encouraged by the use of mirex, which also kills native ants that are highly competitive with the fire ants. The United States Environmental Protection Agency prohibited its use in 1976. It is prohibited by the Stockholm Convention on Persistent Organic Pollutants.
A larvicide is an insecticide that is specifically targeted against the larval life stage of an insect. Their most common use is against mosquitoes. Larvicides may be contact poisons, stomach poisons, growth regulators, or (increasingly) biological control agents.
Brodifacoum is a highly lethal 4-hydroxycoumarin vitamin K antagonist anticoagulant poison. In recent years, it has become one of the world's most widely used pesticides. It is typically used as a rodenticide, but is also used to control larger pests such as possums.
Lonza Group is a Swiss multinational manufacturing company for the pharmaceutical, biotechnology and nutrition sectors, headquartered in Basel, with major facilities in Europe, North America and South Asia. Lonza was established under that name in the late 19th-century in Switzerland. The company provides product development services to the pharmaceutical and biologic industries, including custom manufacturing of biopharmaceuticals and detection systems and services for the bioscience sector.
Ferric sodium EDTA, also known as sodium ferric ethylenediaminetetraacetate, is a broad spectrum molluscicide used to kill snails and slugs and protect agricultural crops and garden plants, and in particular to eliminate infestations of Cornu aspersum, the common garden snail.
Food products and household items commonly handled by humans can be toxic to dogs. The symptoms can range from simple irritation to digestion issues, behavioral changes, and even death. The categories of common items ingested by dogs include food products, human medication, household detergents, indoor and outdoor toxic plants, and rat poison.