Myclobutanil

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.

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
3D model (JSmol)
7138849
ChEBI
ChemSpider
ECHA InfoCard 100.101.000
EC Number
  • 410-400-0
KEGG
MeSH Systhane
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 ☒N
    Key: HZJKXKUJVSEEFU-UHFFFAOYSA-N ☒N
  • CCCCC(Cn1cncn1)(C#N)c1ccc(Cl)cc1
Properties
C15H17ClN4
Molar mass 288.78 g·mol−1
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
142 mg⋅dm−3
Hazards
GHS labelling:
GHS07: Exclamation mark GHS08: Health hazard GHS09: Environmental hazard
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).
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Infobox references

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.[2]

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]

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".
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