Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Aldicarb: Difference between pages

{{short description|Chemical compound (insecticide)}}

| verifiedrevid = 477316816

| ImageSize =

| ImageSize1 =

| SMILES = CNC(=O)O/N=C/C(C)(C)SC

| RTECS = UE2275000

| EINECS = 204-123-2

| Appearance = colorless crystals

| Odor = faint sulfur odor

| Density = 1.195 g/cm²

| MeltingPtC = 99.5

| BoilingPtC = 251

| Solubility = 0.573 g/100 mL

| SolubleOther = soluble in [[acetone]], [[benzene]], [[chlorobenzene]], [[diethyl ether]], [[isopropyl alcohol]], [[methylene chloride]], [[toluene]] <br> slightly soluble in [[xylene]]

| Section3 = {{Chembox Hazards

| LD50 = 0.84 mg/kg (oral, rats)<ref>{{cite journal|title=Controlled release of aldicarb from carboxymethyl cellulose microspheres: in vitro and field applications|journal=Pesticide Science|volume=55|issue=12|pages=1194–1202|doi=10.1002/(sici)1096-9063(199912)55:12<1194::aid-ps79>3.0.co;2-h|year=1999|last1=Kök|first1=Fatma N|last2=Arıca|first2=M Yakup|last3=Gencer|first3=Oktay|last4=Abak|first4=Kazım|last5=Hasırcı|first5=Vasıf}}</ref>

}}

'''Aldicarb''' is a [[carbamate insecticide]] which is the active substance in the pesticide '''Temik'''. It is effective against [[thrips]], [[aphid]]s, [[Red Spider Mite|spider mite]]s, [[lygus]], fleahoppers, and leafminers, but is primarily used as a [[nematicide]].<ref>{{cite web|url=http://www.bayercropscience.us/products/insecticides/temik|title=Temik|website=www.bayercropscienceus.us|access-date=2011-04-01}}</ref> Aldicarb is a [[cholinesterase]] inhibitor which prevents the breakdown of acetylcholine in the synapse. Aldicarb is considered "[[EPA list of extremely hazardous substances|extremely hazardous]]" by the [[United States Environmental Protection Agency|EPA]] and [[World Health Organization]] and has been banned in more than 100 countries.<ref name="Hettinger">{{cite news |last1=Hettinger |first1=Johnathan |title=EPA considers approving fruit pesticide despite risks to children, records show |url=https://www.theguardian.com/environment/2023/nov/21/epa-fruit-pesticide-risk-children-aldicarb |access-date=21 November 2023 |work=The Guardian |date=21 November 2023}}</ref> In case of severe poisoning, the victim dies of respiratory failure.

Aldicarb was first synthesized in 1965 by Payne and Weiden, and was sold on the market for the first time in 1970.<ref name="pubs.acs.org">{{cite journal |last1=Payne |first1=L. K. Jr. |last2=Stansbury |first2=H. A. Jr. |last3=Weiden |first3=M. H. J. |title=Synthesis and Insecticidal Properties of Some Cholinergic Trisubstituted Acetaldehyde O-(Methylcarbamoyl)oximes |journal=Journal of Agricultural and Food Chemistry |date=July 1, 1966 |volume=14 |issue=4 |pages=356–365 |doi=10.1021/jf60146a007 |url=https://pubs.acs.org/doi/pdf/10.1021/jf60146a007 |access-date=November 7, 2021}}</ref> The synthesis of aldicarb results in both the E and Z isomers.<ref name="PubChem - Aldicarb CID: 9570071">{{cite web |title=PubChem - Aldicarb (CID: 9570071) |url=https://pubchem.ncbi.nlm.nih.gov/compound/9570071 |website=PubChem |publisher=National Library of Medicine |access-date=November 7, 2021}}</ref>

Aldicarb is effective where resistance to [[organophosphate]] [[insecticide]]s has developed, and is extremely important in [[potato]] production, where it is used for the control of soil-borne [[nematode]]s and some foliar pests. Its high level of solubility restricts its use in certain areas where the [[water table]] is close to the surface.

==Regulatory status==

In the United States, aldicarb was approved by the EPA for use by professional pesticide applicators on a variety of crops, including cotton, beans, and others. It is not approved for household use.<ref>{{cite web|url=http://extoxnet.orst.edu/pips/aldicarb.htm|title=Aldicarb|date=June 1996|website=extoxnet.orst.edu|publisher=The Extension Toxicology Network|access-date=2007-08-13}}</ref> The EPA started limiting the main aldicarb pesticide, Temik 15G, in 2010, requiring an end to distribution by 2017.{{citation needed|date=March 2017}} Discontinuation of the use on citrus and potatoes began in 2012, with a complete phase out of the product expected by 2018.<ref name="SciAmerican2010">{{cite web

| date = August 18, 2010

| website = [[Scientific American]]

| url = https://www.scientificamerican.com/article/toxic-pesticide-banned-after-decades-of-use/

| title = Toxic Pesticide Banned after Decades of Use

| access-date = 2012-12-03 }}</ref> A new aldicarb pesticide named AgLogic 15G, was approved by the EPA in December 2011 and is said to be entering the market in 2015.<ref>{{cite web

| date = 2014

| publisher = AgLogic Chemical

| website = [[AgLogic]]

| url = http://www.aglogicchemical.com/

| title = AgLogic/Meymik 15 G Homepage

| access-date = 2015-10-02

}}</ref>{{update inline|date=March 2017}} It will be registered for use on cotton, dry beans, peanuts, soybeans, sugar beets, and sweet potatoes.{{update inline|date=March 2017}}

Tres Pasitos, a mouse, rat, and roach killer that contains high concentrations of aldicarb, has been illegally imported into the United States from Mexico and other Latin American countries. The product is highly toxic to animals and people, and according to the EPA "should never be used in [the] home."<ref name="EPA">[https://www.epa.gov/safepestcontrol/avoid-illegal-household-pesticide-products Avoid Illegal Household Pesticide Products], US Environmental Protection Agency</ref>

Most commonly, aldicarb causes toxic symptoms when it is ingested through food that has been tainted with the insecticide.<ref name="PubChem - Aldicarb CID: 9570071"/> Once in the body, aldicarb is broken down into aldicarb sulfone and aldicarb sulfoxide. Hydrolysis of aldicarb leads to aldicarb oximes and aldicarb nitriles to reverse the toxicity.<ref>{{cite web |title=PubChem - Aldicarb (CID: 0570071) |url=https://pubchem.ncbi.nlm.nih.gov/compound/9570071 |website=PubChem |access-date=November 7, 2021}}</ref>

Aldicarb is classified as an [[List of extremely hazardous substances|extremely hazardous substance]] in the United States as defined in Section 302 of the U.S. [[Emergency Planning and Community Right-to-Know Act]] (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.<ref name="gov-right-know">{{Cite journal | publisher = [[United States Government Publishing Office|Government Printing Office]] | title = 40 C.F.R.: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities | url = http://edocket.access.gpo.gov/cfr_2008/julqtr/pdf/40cfr355AppA.pdf | edition = July 1, 2008 | access-date = October 29, 2011 | archive-url = https://web.archive.org/web/20120225051612/http://edocket.access.gpo.gov/cfr_2008/julqtr/pdf/40cfr355AppA.pdf | archive-date = February 25, 2012 | url-status = dead }}</ref>

The use of aldicarb has been prohibited in Europe since 2003 due to concerns over the impact on non-target organisms.<ref name="rotterdam">{{cite web |title=Decision Guidance Document ALDICARB |url=http://www.pic.int/Portals/5/DGDs/DGD_Aldicarb_EN.pdf |publisher=Secretariat of the Rotterdam Convention on the Prior Informed Consent Procedure for Certain Hazardous Chemicals and Pesticides in International Trade |access-date=11 July 2023}}</ref>

==History==

Aldicarb is manufactured by [[Bayer CropScience]], but was formerly owned and produced by [[Union Carbide]]. Union Carbide's agricultural chemicals division was sold to [[Rhône-Poulenc]]. Later, [[Aventis]] Cropscience was formed from [[Hoechst AG]] and Rhone-Poulenc Agrochemical, which lasted until Bayer acquired it in 2002.

In August 1979, groundwater wells in Suffolk County, NY were contaminated with aldicarb residue due to irrigated potato fields nearby. Of the approximately 8,400 wells tested, 13.5% contained more than 7&nbsp;ug/L of aldicarb, which exceeds standard guidelines.<ref>{{cite book |last1=International Agency for Research on Cancer |title=Occupational Exposures in Insecticide Application, and Some Pesticides |date=1991 |publisher=World Health Organization |location=Lyon, France |pages=93–113 |url=https://www.ncbi.nlm.nih.gov/books/NBK499618/pdf/Bookshelf_NBK499618.pdf |access-date=November 7, 2021}}</ref>

In July 1985, aldicarb present in watermelons grown in California caused an outbreak of pesticide food poisoning which affected over 2,000 people, and led to a temporary ban on watermelon sales.<ref name="SciAmerican2010" />

In November 2009, corn treated with Temik was placed in and around [[peanut]] fields in [[Eastland County, Texas]], near the town of [[Cisco, Texas|Cisco]]. The corn was eaten by [[feral hog]]s, [[deer]], and other animals, prompting the [[Texas Parks and Wildlife Department]] to issue a [[hunting]] ban.<ref>[http://www.tpwd.state.tx.us/newsmedia/releases/?req=20091105i Authorities Investigate Contaminated Corn in Eastland County], Texas Parks and Wildlife Department, Nov. 5, 2009</ref>

==Toxicity in mammals==

Aldicarb is a fast-acting cholinesterase inhibitor, causing rapid accumulation of acetylcholine at the synaptic cleft. The aldicarb structure is similar to that of acetylcholine, therefore improving its binding to acetylcholinesterase in the body.<ref name="pubs.acs.org"/>

It is widely used to study cholinergic neurotransmission in simple systems such as the nematode ''[[Caenorhabditis elegans|C. elegans]]''.

Exposure to high amounts of aldicarb can cause weakness, blurred vision, headache, nausea, tearing, sweating, and tremors in humans. High doses can be fatal to humans because it can paralyze the respiratory system.<ref name="EPA"/>

In [[South Africa]] (where Aldicarb is popularly known as Two Step) it is widely used by burglars to poison dogs.<ref>[http://www.iol.co.za/news/south-africa/criminals-target-dogs-with-poison-1.281169 Criminals target dogs with poison], IOL News, June 11, 2006</ref><ref>[http://southafricatoday.net/south-africa-news/dog-poisoning-with-the-intention-to-break-into-houses/ Dog poisoning with the intention to break into houses], South Africa Today, July 10, 2014</ref><ref>{{Cite news|url=http://www.news24.com/SouthAfrica/News/Dog-poisoning-plague-hits-city-20150519|title=Dog-poisoning plague hits city|work=News24|access-date=2017-04-21}}</ref>

==Toxicity in birds==

{{LD50}} for a [[mallard]] duck is 1.0&nbsp;mg/kg body weight (acute).<ref name="rotterdam"/> According to the [[Rotterdam Convention]]'s risk assessment, "Ingestion of aldicarb granules poses a great threat to avian species; aldicarb is very toxic to birds and poses a danger to endangered species".<ref name="rotterdam"/>

==References==

{{reflist}}

==External links==

* {{PPDB|19}}

{{insecticides}}

{{Acetylcholine metabolism and transport modulators}}

{{Consumer Food Safety}}

[[Category:Acetylcholinesterase inhibitors]]

[[Category:Carbamate insecticides]]

[[Category:Oxime carbamates]]

[[Category:Thioethers]]

[[Category:Nematicides]]

[[Category:Insecticides]]