Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C15H17ClN4 |
| Molecular Weight | 288.775 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCC(CN1C=NC=N1)(C#N)C2=CC=C(Cl)C=C2
InChI
InChIKey=HZJKXKUJVSEEFU-UHFFFAOYSA-N
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
| Molecular Formula | C15H17ClN4 |
| Molecular Weight | 288.775 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
Myclobutanil is a conazole class fungicide widely used as an agrichemical. It is approved for use on fruit, vegetables and seed commodities in the EU and elsewhere to control fungi such as Ascomycetes, Fungi Imperfecti and, Basidiomycetes. Myclobutanil products are registered and authorized for use in all countries in which they are sold,
including, but not limited to: Australia, Canada, India, New Zealand, South Africa, the European
Union and the United States. Its mode of action is inhibition of the enzyme C14 demethylase which is involved
in the synthesis of ergosterol, a component of fungal cellular membranes.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Estimation of estrogenic and antiestrogenic activities of selected pesticides by MCF-7 cell proliferation assay. | 2004 May |
|
| Transcriptional profiles in liver from rats treated with tumorigenic and non-tumorigenic triazole conazole fungicides: Propiconazole, triadimefon, and myclobutanil. | 2006 |
|
| Transcriptional profiles in liver from mice treated with hepatotumorigenic and nonhepatotumorigenic triazole conazole fungicides: Propiconazole, triadimefon, and myclobutanil. | 2006 |
|
| Comparison of lanosterol-14 alpha-demethylase (CYP51) of human and Candida albicans for inhibition by different antifungal azoles. | 2006 Nov 10 |
|
| Gene expression profiling in the liver of CD-1 mice to characterize the hepatotoxicity of triazole fungicides. | 2006 Sep 15 |
|
| Gene expression profiling in liver and testis of rats to characterize the toxicity of triazole fungicides. | 2006 Sep 15 |
|
| Induction of cytochrome P450 enzymes in rat liver by two conazoles, myclobutanil and triadimefon. | 2007 Feb |
|
| Disruption of testosterone homeostasis as a mode of action for the reproductive toxicity of triazole fungicides in the male rat. | 2007 Jan |
|
| Toxicogenomic study of triazole fungicides and perfluoroalkyl acids in rat livers predicts toxicity and categorizes chemicals based on mechanisms of toxicity. | 2007 Jun |
|
| Mode of action for reproductive and hepatic toxicity inferred from a genomic study of triazole antifungals. | 2009 Aug |
|
| Three conazoles increase hepatic microsomal retinoic acid metabolism and decrease mouse hepatic retinoic acid levels in vivo. | 2009 Jan 15 |
|
| Toxicogenomic effects common to triazole antifungals and conserved between rats and humans. | 2009 Jul 1 |
|
| Analysis of microRNA and gene expression profiling in triazole fungicide-treated HepG2 cell line. | 2013 Jan 7 |
|
| Concordance of transcriptional and apical benchmark dose levels for conazole-induced liver effects in mice. | 2013 Nov |
|
| Two azole fungicides (carcinogenic triadimefon and non-carcinogenic myclobutanil) exhibit different hepatic cytochrome P450 activities in medaka fish. | 2014 Jul 30 |
|
| The effects of the fungicides fenhexamid and myclobutanil on SH-SY5Y and U-251 MG human cell lines. | 2014 Nov |
|
| Comparison of osteoblast and cardiomyocyte differentiation in the embryonic stem cell test for predicting embryotoxicity in vivo. | 2014 Sep |
|
| Population-based in vitro hazard and concentration-response assessment of chemicals: the 1000 genomes high-throughput screening study. | 2015 May |
Patents
Sample Use Guides
The acute oral LD50 for mice is 1360 mg/kg, and ranges from 1.75 to 1.8 g/kg for rats.
Route of Administration:
Oral
HepG2 cell viability was assessed with the MTT assay after 24 h of exposure to myclobutanil at different
concentrations (range: 0.1–500 ppm). The fungicide reduced cell viability at all
concentrations tested. In particular, the cytotoxic effect was partial from 1 to 10 ppm, but from 100
to 500 ppm there was near total cell death. Indeed, myclobutanil reduced cell viability to <50% at
100 ppm and to <10% at 500 ppm.
| Substance Class |
Chemical
Created
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admin
on
Edited
Sat Dec 16 08:51:41 GMT 2023
by
admin
on
Sat Dec 16 08:51:41 GMT 2023
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| Record UNII |
B6T1JTM6KZ
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| Record Status |
Validated (UNII)
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| Record Version |
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EPA PESTICIDE CODE |
128857
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m7676
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6336
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Myclobutanil
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88671-89-0
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