Myclobutanil

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
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EC Number
  • 410-400-0
KEGG
MeSH Systhane
PubChem CID
RTECS number
  • XZ5257000
UNII
UN number 3077
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,2-3,8,10H2,1H3 ☒N
    Key: HZJKXKUJVSEEFU-UHFFFAOYSA-N ☒N
SMILES
  • CCCCC(Cn1cncn1)(C#N)c1ccc(Cl)cc1
Properties
Chemical formula
 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
Solubility in water
 142 mg⋅dm−3
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 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

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.

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.{{cite web}}: CS1 maint: multiple names: authors list (link)
  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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