Metaldehyde

Metaldehyde is an organic compound with the formula (CH3CHO)4. It is usded as a pesticide against slugs, snails, and other gastropods.[2] It is the cyclic tetramer of acetaldehyde.[3]

Metaldehyde
Names
IUPAC name
2,4,6,8-tetramethyl-1,3,5,7-tetroxocane
Other names
metaldehyde
metacetaldehyde
ethanal tetramer
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.274
EC Number
  • 203-600-2
KEGG
PubChem CID
UNII
UN number 1332
InChI
  • InChI=1S/C8H16O4/c1-5-9-6(2)11-8(4)12-7(3)10-5/h5-8H,1-4H3 N
    Key: GKKDCARASOJPNG-UHFFFAOYSA-N N
  • InChI=1/C8H16O4/c1-5-9-6(2)11-8(4)12-7(3)10-5/h5-8H,1-4H3
    Key: GKKDCARASOJPNG-UHFFFAOYAG
SMILES
  • CC1OC(C)OC(C)OC(C)O1
  • O1C(OC(OC(OC1C)C)C)C
Properties
Chemical formula
 C8H16O4
Molar mass 176.212 g/mol
Density 1.27 g/cm3
Melting point 246 °C (475 °F; 519 K)
Boiling point sublimes at 110 to 120 °C (230 to 248 °F; 383 to 393 K)
Hazards
GHS labelling:[1]
Pictograms
Signal word
 Danger
Hazard statements
 H228, H301, H361f, H412
Precautionary statements
 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).
N verify (what is YN ?)
Infobox references

Production and properties

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.

The D2d stereomer

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.

Uses

As a pesticide
Granules of metaldehyde (trade name Limacide)

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]

Other uses

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.

Safety and toxicity to pets and humans

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.[12][13] 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.[14]

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.[14]

Due to this toxicity, pet owners may want to investigate alternatives which are not as toxic to pets, such as Ferric Sodium EDTA or iron(III) phosphate.[15] 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.[16] Baits may contain a bittering agent 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. [17]

See also

References
  1. "Metaldehyde". pubchem.ncbi.nlm.nih.gov. Retrieved 5 October 2022.
  2. Joyner, Lisa (2022-04-01). "Slug pellets officially banned in the UK". Country Living. Retrieved 2022-04-03.
  3. Marc Eckert, Gerald Fleischmann, Reinhard Jira, Hermann M. Bolt, Klaus Golka "Acetaldehyde" in Ullmann's Encyclopedia of Industrial Chemistry, 2006, Wiley-VCH, Weinheim. doi:10.1002/14356007.a01_031.pub2.
  4. PubChem. "Metaldehyde". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-04-01.
  5. "Metaldehyde Toxicity Slug Bait Poisoning | VCA Animal Hospitals". vcahospitals.com. Retrieved 2022-04-01.
  6. Armstrong, John H. (January 18, 2013). "Frequently Asked Questions about Metaldehyde For Controlling Snails and Slugs" (PDF). Florida Department of Agriculture and Consumer Services. Retrieved April 1, 2022.
  7. Restrictions on the use of metaldehyde to protect wildlife, UK Government, 19 December 2018
  8. Outdoor use of metaldehyde to be banned to protect wildlife, UK Government, 18 September 2020
  9. Eschenmooser, Walter (June 1997). "100 Years of Progress with LONZA". Chimia. 51 (6): 259-269. doi:10.2533/chimia.1997.259. S2CID 100485418. Retrieved 8 October 2020.
  10. Toxicology of metaldehyde
  11. Maher S; et al. (2016). "Direct Analysis and Quantification of Metaldehyde in Water using Reactive Paper Spray Mass Spectrometry". Scientific Reports. 6: 35643. Bibcode:2016NatSR...635643M. doi:10.1038/srep35643. PMC 5073298. PMID 27767044.
  12. Joyner, Lisa (2022-04-01). "Slug pellets officially banned in the UK". Country Living. Retrieved 2022-04-03.
  13. "Pests in Gardens and Landscapes". University of California, Davis. Retrieved 2010-08-03.
  14. "Metaldehyde Poisoning in Animals - Toxicology". Merck Veterinary Manual. Retrieved 2022-04-01.
  15. "Slugging Out Spring". Dr. Heidi Houchen, DVM. Archived from the original on 2012-07-18.
  16. Miller, Reginald (December 1928). "Poisoning by "Meta Fuel" Tablets (Metacetaldehyde)". Archives of Disease in Childhood. 3 (18): 292–295. doi:10.1136/adc.3.18.292. PMC 1975025. PMID 21031743.
  17. Tan YJ.; et al. (2022). "Acute metaldehyde poisoning from ingestion: clinical features and implications for early treatment". Acute Medicine and Surgery. 9. doi:10.1002/ams2.766. PMC 9209800. PMID 35769386.
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