Myclobutanil
{{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| ImageFile = Myclobutanil Grundstruktur V1.svg
| ImageSize = 200px
| ImageFile_Ref = {{chemboximage|correct|??}}
| ImageName = Kekulé, skeletal formula of myclobutanil
| ImageFile2 = Myclobutanil.png
| ImageSize2 = 200px
| ImageName2 = Kekulé, skeletal formula of myclobutanil
| IUPACName = 2-(4-Chlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)hexanenitrile
| OtherNames =
|Section1={{Chembox Identifiers
| CASNo = 88671-89-0
| CASNo_Ref = {{cascite|correct|CAS}}
| PubChem = 6336
| PubChem1 = 11077077
| PubChem1_Comment = (2R)
| PubChem2 = 38989055
| PubChem2_Comment = (2S)
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = B6T1JTM6KZ
| ChemSpiderID = 6096
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID1 = 9252226
| ChemSpiderID1_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID1_Comment = (2R)
| EINECS = 410-400-0
| UNNumber = 3077
| KEGG = C18477
| KEGG_Ref = {{keggcite|correct|kegg}}
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 75281
| MeSHName = Systhane
| RTECS = XZ5257000
| Beilstein = 7138849
| SMILES = CCCCC(Cn1cncn1)(C#N)c1ccc(Cl)cc1
| StdInChI = 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
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = HZJKXKUJVSEEFU-UHFFFAOYSA-N
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
}}
|Section2={{Chembox Properties
| C=15 | H=17 | N=4 | Cl=1
| Appearance = Pale, yellow, translucent crystals
| MeltingPtC = 63 to 68
| BoilingPtC = 202 to 208
| BoilingPt_notes = at 130 Pa
| Solubility = 142{{nbsp}}mg⋅dm−3
}}
|Section3={{Chembox Hazards
| GHSPictograms = {{GHS exclamation mark}} {{GHS health hazard}} {{GHS environment}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|302|319|361|411}}
| PPhrases = {{P-phrases|273|281|305+351+338}}
| NFPA-H = 2
| NFPA-F = 1
| NFPA-R = 0
| FlashPt = >
| FlashPtC = 100
}}
| verifiedrevid = 462256248
}}
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
| class="wikitable" style="text-align:center;" |
| class="hintergrundfarbe6"
! colspan="2" | Myclobutanil (2 stereoisomers) |
| File:(S)-Myclobutanil V1.svg {{small|(S)-configuration}} | File:(R)-Myclobutanil V1.svg |
== 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.{{cite web |title=SAFETY DATA SHEET Myclobutanil |url=https://www.caymanchem.com/msdss/24100m.pdf |publisher=Cayman Chemical Company |access-date=11 August 2021}}
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.{{cite web|url=https://cameochemicals.noaa.gov/chemical/30020|title=MYCLOBUTANIL - CAMEO Chemicals - NOAA|first=NOAA Office of Response and Restoration, US|last=GOV|website=cameochemicals.noaa.gov}}{{cite web | url = http://www.dow.com/webapps/include/GetDoc.aspx?filepath=productsafety/pdfs/noreg/233-01023.pdf&pdf=true | title = Product Safety Assessment: Myclobutanil}}
== 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.{{cite news|url=https://www.theglobeandmail.com/news/national/canadians-not-told-about-banned-pesticide-found-in-medical-marijuana-supply/article33443887/|title=Canadians not told about banned pesticide found in medical pot supply|via=The Globe and Mail}} 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.{{cite web |url=https://www.nbcnews.com/health/vaping/tests-show-bootleg-marijuana-vapes-tainted-hydrogen-cyanide-n1059356 |title=Tests show bootleg marijuana vapes tainted with hydrogen cyanide|website=NBC News}} In Michigan, the current state action limit for myclobutanil is 200 ppb in cannabis products.{{cite web|url=https://www.michigan.gov/documents/lara/Department_Banned_Pesticide_Active_Ingredient_List_620039_7.pdf&pdf=true | title = Technical Bulletin}}
References
{{Reflist}}
External links
- {{PPDB|478}}
- [http://www.inchem.org/documents/jmpr/jmpmono/v92pr13.htm International Programme on Chemical Safety]