Oxamyl

Last updated
Oxamyl
Oxamyl.svg
Oxamyl molecule spacefill.png
Names
IUPAC name
Methyl 2-(dimethylamino)-N-[(methylcarbamoyl)oxy]-2-oxoethanimidothioate
Other names
N,N-Dimethyl-2-methyl-carbamoyloximino-2-(dimethylthio) acetamide; Thioxamyl
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.041.299 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C7H13N3O3S/c1-8-7(12)13-9-5(14-4)6(11)10(2)3/h1-4H3,(H,8,12)
    Key: KZAUOCCYDRDERY-UHFFFAOYSA-N
  • InChI=1/C7H13N3O3S/c1-8-7(12)13-9-5(14-4)6(11)10(2)3/h1-4H3,(H,8,12)
    Key: KZAUOCCYDRDERY-UHFFFAOYAQ
  • CN(C)C(=O)/C(SC)=N/OC(=O)NC
Properties
C7H13N3O3S
Molar mass 219.26 g·mol−1
AppearanceColorless crystalline solid [1]
Density 0.97 g/cm3 [1]
Melting point 100 to 102 °C (212 to 216 °F; 373 to 375 K)
108 to 110 °C (dimorphic) [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Oxamyl is a chemical used as a pesticide that comes in two forms: granulated and liquid. The granulated form has been banned in the United States. [2] It is commonly sold under the trade name Vydate.

Contents

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 (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities. [3]

Structure and uses

Oxamyl is a carbamate pesticide. According to the WHO Food and Agriculture Organization, "Oxamyl is a colourless crystalline solid with a melting point of 100-102 °C changing to a dimorphic form with a melting point of 108-110 °C. It has a slightly sulfurous odour. Oxamyl is non-corrosive. It has a specific gravity of 0.97 (25°/4°)." [1]

According to the United Nations Environment Programme, "This product is efficient in controlling most nematode species in addition to a large number of sucking and chewing insects such as aphids and thrips." Oxamyl is extremely toxic to humans whether ingested, inhaled, or contact with the skin. Its overuse can also lead to residue accumulation in food, [2] though its chemical composition—once coming into contact with the soil—rapidly degrades. [4] Signs of Oxamyl poisoning include: Malaise, muscle weakness, dizziness, sweating, Headache, salivation, nausea, vomiting, abdominal pain, Miosis with blurred vision, incoordination, muscle twitching and slurred speech—though symptoms can worsen with severe poisoning. According to the Food and Agriculture Organization, "Contact with the skin, inhalation of dust or spray, or swallowing may be fatal." [1]

Because of its toxicity, its use is restricted in the EU/UK with maximum residue limits for apples and oranges being 0.01 mg/kg[ citation needed ] and this amount is only allowed because this is the limit of detection. Despite those limits, a 2023 review by the European Food Safety Authority identified areas of concern and chronic consumer exposure concerns. [5] [6]

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">Poison</span> Substance that causes death, injury or harm to organs

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.

<span class="mw-page-title-main">Lindane</span> Organochlorine chemical and an isomer of hexachlorocyclohexane

Lindane, also known as gamma-hexachlorocyclohexane (γ-HCH), gammaxene, Gammallin and benzene hexachloride (BHC), is an organochlorine chemical and an isomer of hexachlorocyclohexane that has been used both as an agricultural insecticide and as a pharmaceutical treatment for lice and scabies.

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

<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.

Pesticides vary in their effects on bees. Contact pesticides are usually sprayed on plants and can kill bees when they crawl over sprayed surfaces of plants or other areas around it. Systemic pesticides, on the other hand, are usually incorporated into the soil or onto seeds and move up into the stem, leaves, nectar, and pollen of plants.

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.

<span class="mw-page-title-main">Aldicarb</span> Chemical compound (insecticide)

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. In case of severe poisoning, the victim dies of respiratory failure.

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

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.

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

Toxaphene was an insecticide used primarily for cotton in the southern United States during the late 1960s and the 1970s. Toxaphene is a mixture of over 670 different chemicals and is produced by reacting chlorine gas with camphene. It can be most commonly found as a yellow to amber waxy solid.

Pesticide residue refers to the pesticides that may remain on or in food, after they are applied to food crops. The maximum allowable levels of these residues in foods are often stipulated by regulatory bodies in many countries. Regulations such as pre-harvest intervals also often prevent harvest of crop or livestock products if recently treated in order to allow residue concentrations to decrease over time to safe levels before harvest. Exposure of the general population to these residues most commonly occurs through consumption of treated food sources, or being in close contact to areas treated with pesticides such as farms or lawns.

<span class="mw-page-title-main">Chlorothalonil</span> Fungicide

Chlorothalonil (2,4,5,6-tetrachloroisophthalonitrile) is an organic compound mainly used as a broad spectrum, nonsystemic fungicide, with other uses as a wood protectant, pesticide, acaricide, and to control mold, mildew, bacteria, algae. Chlorothalonil-containing products are sold under the names Bravo, Echo, and Daconil. It was first registered for use in the US in 1966. In 1997, the most recent year for which data are available, it was the third most used fungicide in the US, behind only sulfur and copper, with 12 million pounds used in agriculture that year. Including nonagricultural uses, the United States Environmental Protection Agency (EPA) estimates, on average, almost 15 million lb (6.8 million kg) were used annually from 1990 to 1996.

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

Endrin is an organochlorine compound 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.

<span class="mw-page-title-main">Toxicity class</span> Pesticide classification system

Toxicity class refers to a classification system for pesticides that has been created by a national or international government-related or -sponsored organization. It addresses the acute toxicity of agents such as soil fumigants, fungicides, herbicides, insecticides, miticides, molluscicides, nematicides, or rodenticides.

<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.

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

Crimidine is a convulsant poison used as a rodenticide. Crimidine was originally known by its product name, Castrix. It was originally produced in the 1940s by the conglomerate, IG Farben. 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. It is also no longer used in the United States as a rodenticide, but is still used to this day in other countries.

<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">Terbufos</span> Chemical compound

Terbufos is a chemical compound used in insecticides and nematicides. It is part of the chemical family of organophosphates. It is a clear, colourless to pale yellow or reddish-brown liquid and sold commercially as granulate.

<span class="mw-page-title-main">Regulation of pesticides in the European Union</span>

A pesticide, also called Plant Protection Product (PPP), which is a term used in regulatory documents, consists of several different components. The active ingredient in a pesticide is called “active substance” and these active substances either consist of chemicals or micro-organisms. The aims of these active substances are to specifically take action against organisms that are harmful to plants. In other words, active substances are the active components against pests and plant diseases.

References

  1. 1 2 3 4 5 "DATA SHEETS ON PESTICIDES No. 54 - 1983 - OXAMYL". WORLD HEALTH ORGANIZATION FOOD AND AGRICULTURE ORGANIZATION. 1983. Archived from the original on 5 January 2012. Retrieved 30 January 2012.
  2. 1 2 United Nations Environment Programme, United Nations Environment Programme. Division of Technology, Industry, and Economics. Economics and Trade Unit, United Nations Development Programme, Envirotech Ltd (2005). Effects of trade liberalization on agriculture in Lebanon: with special focus on products where methyl bromide is used. UNEP/Earthprint. p. 22.{{cite book}}: CS1 maint: multiple names: authors list (link)
  3. "40 C.F.R.: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities" (PDF) (July 1, 2008 ed.). Government Printing Office. Archived from the original (PDF) on February 25, 2012. Retrieved October 29, 2011.{{cite journal}}: Cite journal requires |journal= (help)
  4. "OXAMYL". Extension Toxicology Network. 1993. Retrieved 30 January 2012.
  5. "Statement on the risk assessment of maximum residue levels (MRLs) for oxamyl in view of consumer protection | EFSA". www.efsa.europa.eu. 2023-03-01. Retrieved 2023-11-16.
  6. "Peer review of the pesticide risk assessment of the active substance oxamyl | EFSA". www.efsa.europa.eu. 2022-05-18. Retrieved 2023-11-16.