Myclobutanil

Last updated
Myclobutanil
Myclobutanil Grundstruktur V1.svg
Myclobutanil.png
Names
IUPAC name
2-(4-Chlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)hexanenitrile
Identifiers
3D model (JSmol)
7138849
ChEBI
ChemSpider
ECHA InfoCard 100.101.000 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 410-400-0
KEGG
MeSH Systhane
PubChem CID
RTECS number
  • XZ5257000
UNII
UN number 3077
  • InChI=1S/C15H17ClN4/c1-2-3-8-15(9-17,10-20-12-18-11-19-20)13-4-6-14(16)7-5-13/h4-7,11-12H,2-3,8,10H2,1H3 X mark.svgN
    Key: HZJKXKUJVSEEFU-UHFFFAOYSA-N X mark.svgN
  • CCCCC(Cn1cncn1)(C#N)c1ccc(Cl)cc1
Properties
C15H17ClN4
Molar mass 288.78 g·mol−1
AppearancePale, yellow, translucent crystals
Melting point 63 to 68 °C (145 to 154 °F; 336 to 341 K)
Boiling point 202 to 208 °C (396 to 406 °F; 475 to 481 K) at 130 Pa
142 mg⋅dm−3
Hazards
GHS labelling:
GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg GHS-pictogram-pollu.svg
Warning
H302, H319, H361, H411
P273, P281, P305+P351+P338
NFPA 704 (fire diamond)
2
1
0
Flash point >100 °C (212 °F; 373 K)
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 ?)

Myclobutanil is a triazole chemical used as a fungicide. It is a steroid demethylation inhibitor, specifically inhibiting ergosterol biosynthesis. [1] Ergosterol is a critical component of fungal cell membranes.

Contents

Stereoisomerism

Myclobutanil (2 stereoisomers)
(S)-Myclobutanil V1.svg
(S)-configuration
(R)-Myclobutanil V1.svg
(R)-configuration

Safety

The Safety Data Sheet indicates the following hazards:

The first hazard has caused this chemical to be placed on the 1986 California Proposition 65 toxics list.

When heated, myclobutanil decomposes to produce corrosive and/or toxic fumes, including carbon monoxide, carbon dioxide, hydrogen chloride, hydrogen cyanide, and nitrogen oxides. [3] [4]

Banned for cannabis cultivation

Myclobutanil is banned in Canada, Colorado, Washington, Oregon, and Oklahoma for the production of medical and recreational cannabis. In 2014, a Canadian news investigation by The Globe and Mail reported the discovery of myclobutanil in medical cannabis produced by at least one government licensed grower. [5] In September 2019, NBC News commissioned CannaSafe to test THC cartridges for heavy metals, pesticides, and residual solvents like Vitamin E; pesticides, including myclobutanil, was found in products from unlicensed dealers. [6] In Michigan, the current state action limit for myclobutanil is 200 ppb in cannabis products. [7]

Related Research Articles

<span class="mw-page-title-main">Cyanide</span> Any molecule with a cyano group (–C≡N)

In chemistry, a cyanide is a chemical compound that contains a C≡N functional group. This group, known as the cyano group, consists of a carbon atom triple-bonded to a nitrogen atom.

In toxicology, the median lethal dose, LD50 (abbreviation for "lethal dose, 50%"), LC50 (lethal concentration, 50%) or LCt50 is a toxic unit that measures the lethal dose of a toxin, radiation, or pathogen. The value of LD50 for a substance is the dose required to kill half the members of a tested population after a specified test duration. LD50 figures are frequently used as a general indicator of a substance's acute toxicity. A lower LD50 is indicative of increased toxicity.

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

Sodium cyanide is a poisonous compound with the formula NaCN. It is a white, water-soluble solid. Cyanide has a high affinity for metals, which leads to the high toxicity of this salt. Its main application, in gold mining, also exploits its high reactivity toward metals. It is a moderately strong base.

Acetonitrile, often abbreviated MeCN, is the chemical compound with the formula CH3CN and structure H3C−C≡N. This colourless liquid is the simplest organic nitrile. It is produced mainly as a byproduct of acrylonitrile manufacture. It is used as a polar aprotic solvent in organic synthesis and in the purification of butadiene. The N≡C−C skeleton is linear with a short C≡N distance of 1.16 Å.

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

Carbon tetrachloride, also known by many other names (such as tetrachloromethane, also recognised by the IUPAC, carbon tet in the cleaning industry, Halon-104 in firefighting, and Refrigerant-10 in HVACR) is an organic compound with the chemical formula CCl4. It is a colourless liquid with a "sweet" smell that can be detected at low levels. It is practically incombustible at lower temperatures. It was formerly widely used in fire extinguishers, as a precursor to refrigerants and as a cleaning agent, but has since been phased out because of environmental and safety concerns. Exposure to high concentrations of carbon tetrachloride (including vapor) can affect the central nervous system and degenerate the liver and kidneys. Prolonged exposure can be fatal.

Acrylonitrile is an organic compound with the formula CH2CHCN and the structure H2C=CH−C≡N. It is a colorless, volatile liquid although commercial samples can be yellow due to impurities. It has a pungent odor of garlic or onions. In terms of its molecular structure, it consists of a vinyl group linked to a nitrile. It is an important monomer for the manufacture of useful plastics such as polyacrylonitrile. It is reactive and toxic at low doses. Acrylonitrile was first synthesized by the French chemist Charles Moureu (1863–1929) in 1893.

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

Potassium cyanide is a compound with the formula KCN. This colorless crystalline salt, similar in appearance to sugar, is highly soluble in water. Most KCN is used in gold mining, organic synthesis, and electroplating. Smaller applications include jewellery for chemical gilding and buffing.

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

Carbaryl is a chemical in the carbamate family used chiefly as an insecticide. It is a white crystalline solid previously sold under the brand name Sevin, which was a trademark of the Bayer Company. The Sevin trademark has since been acquired by GardenTech, which has eliminated carbaryl from most Sevin formulations. Union Carbide discovered carbaryl and introduced it commercially in 1958. Bayer purchased Aventis CropScience in 2002, a company that included Union Carbide pesticide operations. Carbaryl was the third-most-used insecticide in the United States for home gardens, commercial agriculture, and forestry and rangeland protection. As a veterinary drug, it is known as carbaril (INN).

<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.

A blood agent is a toxic chemical agent that affects the body by being absorbed into the blood. Blood agents are fast-acting, potentially lethal poisons that typically manifest at room temperature as volatile colorless gases with a faint odor. They are either cyanide- or arsenic-based.

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

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. 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.

Iodomethane, also called methyl iodide, and commonly abbreviated "MeI", is the chemical compound with the formula CH3I. It is a dense, colorless, volatile liquid. In terms of chemical structure, it is related to methane by replacement of one hydrogen atom by an atom of iodine. It is naturally emitted by rice plantations in small amounts. It is also produced in vast quantities estimated to be greater than 214,000 tons annually by algae and kelp in the world's temperate oceans, and in lesser amounts on land by terrestrial fungi and bacteria. It is used in organic synthesis as a source of methyl groups.

<span class="mw-page-title-main">Thallium(I) sulfate</span> Chemical compound

Thallium(I) sulfate (Tl2SO4) or thallous sulfate is the sulfate salt of thallium in the common +1 oxidation state, as indicated by the Roman numeral I. It is often referred to as simply thallium sulfate.

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

Mirex was 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.

<span class="mw-page-title-main">Globally Harmonized System of Classification and Labelling of Chemicals</span> International standard managed by the United Nations

The Globally Harmonized System of Classification and Labelling of Chemicals (GHS) is an internationally agreed-upon standard managed by the United Nations that was set up to replace the assortment of hazardous material classification and labelling schemes previously used around the world. Core elements of the GHS include standardized hazard testing criteria, universal warning pictograms, and harmonized safety data sheets which provide users of dangerous goods with a host of information. The system acts as a complement to the UN Numbered system of regulated hazardous material transport. Implementation is managed through the UN Secretariat. Although adoption has taken time, as of 2017, the system has been enacted to significant extents in most major countries of the world. This includes the European Union, which has implemented the United Nations' GHS into EU law as the CLP Regulation, and United States Occupational Safety and Health Administration standards.

Right to know is a human right enshrined in law in several countries. UNESCO defines it as the right for people to "participate in an informed way in decisions that affect them, while also holding governments and others accountable". It pursues universal access to information as essential foundation of inclusive knowledge societies. It is often defined in the context of the right for people to know about their potential exposure to environmental conditions or substances that may cause illness or injury, but it can also refer more generally to freedom of information or informed consent.

<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 and other insects.

<span class="mw-page-title-main">Pesticide regulation in the United States</span>

Pesticide regulation in the United States is primarily a responsibility of the Environmental Protection Agency (EPA). In America, it was not till the 1950s that pesticides were regulated in terms of their safety. The Pesticides Control Amendment (PCA) of 1954 was the first time Congress passed guidance regarding the establishment of safe limits for pesticide residues on food. It authorized the Food and Drug Administration (FDA) to ban pesticides they determined to be unsafe if they were sprayed directly on food. The Food Additives Amendment, which included the Delaney Clause, prohibited the pesticide residues from any carcinogenic pesticides in processed food. In 1959, pesticides were required to be registered.

The Hazard Communication Standard requires employers in the United States to disclose toxic and hazardous substances in workplaces. This is related to the Worker Protection Standard.

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

Cyanazine is a herbicide that belongs to the group of triazines. Cyanazine inhibits photosynthesis and is therefore used as a herbicide.

References

  1. "Myclobutanil Product Sheet". Kingtai Chemicals Co.
  2. "SAFETY DATA SHEET Myclobutanil" (PDF). Cayman Chemical Company. Retrieved 11 August 2021.
  3. GOV, NOAA Office of Response and Restoration, US. "MYCLOBUTANIL - CAMEO Chemicals - NOAA". cameochemicals.noaa.gov.
  4. "Product Safety Assessment: Myclobutanil".
  5. "Canadians not told about banned pesticide found in medical pot supply" via The Globe and Mail.
  6. "Tests show bootleg marijuana vapes tainted with hydrogen cyanide". NBC News .
  7. "Technical Bulletin".