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Myclobutanil

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Myclobutanil
Kekulé, skeletal formula of myclobutanil
Kekulé, skeletal formula of myclobutanil
Names
IUPAC name 2-(4-Chlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)hexanenitrile
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 7138849
ChEBI
ChemSpider
ECHA InfoCard 100.101.000 Edit this at Wikidata
EC Number
  • 410-400-0
KEGG
MeSH Systhane
PubChem CID
RTECS number
  • XZ5257000
UNII
UN number 3077
CompTox Dashboard (EPA)
InChI
  • 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,2-3,8,10H2,1H3Key: HZJKXKUJVSEEFU-UHFFFAOYSA-N
SMILES
  • CCCCC(Cn1cncn1)(C#N)c1ccc(Cl)cc1
Properties
Chemical formula C15H17ClN4
Molar mass 288.78 g·mol
Appearance Pale, 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
Solubility in water 142 mg⋅dm
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark GHS08: Health hazard GHS09: Environmental hazard
Signal word Warning
Hazard statements H302, H319, H361, H411
Precautionary statements P273, P281, P305+P351+P338
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Myclobutanil is a triazole chemical used as a fungicide. It is a steroid demethylation (CYP51) inhibitor, specifically inhibiting ergosterol biosynthesis. Ergosterol is a critical component of fungal cell membranes.

Stereoisomerism

Myclobutanil (2 stereoisomers)
(S)-Pefurazoat
(S)-configuration 		(R)-Pefurazoat
(R)-configuration

Safety

The Safety Data Sheet indicates the following hazards:

  • Suspected of damaging fertility or the unborn child.
  • Toxic to aquatic life with long lasting effects.

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.

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. 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. In Michigan, the current state action limit for myclobutanil is 200 ppb in cannabis products.

References

  1. "SAFETY DATA SHEET Myclobutanil" (PDF). Cayman Chemical Company. Retrieved 11 August 2021.
  2. GOV, NOAA Office of Response and Restoration, US. "MYCLOBUTANIL - CAMEO Chemicals - NOAA". cameochemicals.noaa.gov.{{cite web}}: CS1 maint: multiple names: authors list (link)
  3. "Product Safety Assessment: Myclobutanil".
  4. "Canadians not told about banned pesticide found in medical pot supply" – via The Globe and Mail.
  5. "Tests show bootleg marijuana vapes tainted with hydrogen cyanide". NBC News.
  6. "Technical Bulletin".

External links

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