Details
| Stereochemistry | MIXED |
| Molecular Formula | C15H18ClN3O |
| Molecular Weight | 291.776 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 0 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C1CC1)C(O)(CN2C=NC=N2)C3=CC=C(Cl)C=C3
InChI
InChIKey=UFNOUKDBUJZYDE-UHFFFAOYSA-N
InChI=1S/C15H18ClN3O/c1-11(12-2-3-12)15(20,8-19-10-17-9-18-19)13-4-6-14(16)7-5-13/h4-7,9-12,20H,2-3,8H2,1H3
| Molecular Formula | C15H18ClN3O |
| Molecular Weight | 291.776 |
| Charge | 0 |
| Count |
|
| Stereochemistry | MIXED |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Cyproconazole is an azole fungicide, introduced to the market by Sandoz (now Syngenta). It is used to control a wide range of fungi on cereal crops, coffee, sugar beet, fruit trees, grapes, including rust on cereal crops, powdery mildew on cereal crops, fruit tree and grapes, and scab on apple. The cyproconazole structure exists in four stereoisomeric forms as two diastereoisomeric pairs of enantiomers. Cyproconazole is a 1:1 mixture of the two diastereomeric pairs, each of which is a 1:1 mixture of the enantiomers (i.e., all four stereoisomers are present in similar amounts). Cyproconazole inhibits the fungal enzyme eburicol 14-alpha-demethylase, which is involved in the biosynthesis of sterol, a component of a fungal cell wall.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Hepatotoxic effects of (tri)azole fungicides in a broad dose range. | 2015-11 |
|
| Grouping of histone deacetylase inhibitors and other toxicants disturbing neural crest migration by transcriptional profiling. | 2015-09 |
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| Involvement of constitutive androstane receptor in liver hypertrophy and liver tumor development induced by triazole fungicides. | 2015-04 |
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| Combination effects of (tri)azole fungicides on hormone production and xenobiotic metabolism in a human placental cell line. | 2014-09-17 |
|
| Concordance of transcriptional and apical benchmark dose levels for conazole-induced liver effects in mice. | 2013-11 |
|
| Dose-response involvement of constitutive androstane receptor in mouse liver hypertrophy induced by triazole fungicides. | 2013-07-31 |
|
| Triazole induced concentration-related gene signatures in rat whole embryo culture. | 2012-09 |
|
| The hepatocarcinogenic conazoles: cyproconazole, epoxiconazole, and propiconazole induce a common set of toxicological and transcriptional responses. | 2012-05 |
|
| Transcriptomic concentration-response evaluation of valproic acid, cyproconazole, and hexaconazole in the neural embryonic stem cell test (ESTn). | 2012-02 |
|
| Chemical class-specific gene expression changes in the zebrafish embryo after exposure to glycol ether alkoxy acids and 1,2,4-triazole antifungals. | 2011-09 |
|
| Activity profiles of 309 ToxCast™ chemicals evaluated across 292 biochemical targets. | 2011-03-28 |
|
| Occurrence and removal of fungicides in municipal sewage treatment plant. | 2010-03-15 |
|
| Fungicide dissipation and impact on metolachlor aerobic soil degradation and soil microbial dynamics. | 2010-02-15 |
|
| Simultaneous enantioseparation of cyproconazole, bromuconazole, and diniconazole enantiomers by CD-modified MEKC. | 2009-06 |
|
| In vitro toxicity of selected fungicides from the groups of benzimidazoles and demethylation inhibitors to Cladobotryum dendroides and Agaricus bisporus. | 2009-05 |
|
| The effect of fungicides on seed yield and disease control in Italian ryegrass. | 2009 |
|
| Development of monoclonal immunoassays for the determination of triazole fungicides in fruit juices. | 2008-10-08 |
|
| Photocatalytic degradation of pesticides in pure water and a commercial agricultural solution on TiO2 coated media. | 2008-01 |
|
| Mouse liver effects of cyproconazole, a triazole fungicide: role of the constitutive androstane receptor. | 2007-09 |
|
| Capabilities of different liquid chromatography tandem mass spectrometry systems in determining pesticide residues in food. Application to estimate their daily intake. | 2007-07-20 |
|
| Sexual reproduction facilitates the adaptation of parasites to antagonistic host environments: Evidence from empirical study in the wheat-Mycosphaerella graminicola system. | 2007-07 |
|
| MgMfs1, a major facilitator superfamily transporter from the fungal wheat pathogen Mycosphaerella graminicola, is a strong protectant against natural toxic compounds and fungicides. | 2007-05 |
|
| Testing estrogenicity of known and novel (xeno-)estrogens in the MolDarT using developing zebrafish (Danio rerio). | 2007-04 |
|
| Use of SPE-GC/EIMS for residue analysis in wine elaborated from musts spiked with formulations of chlorpyriphos-methyl, methiocarb, dicofol, and cyproconazol. | 2007-03 |
|
| The toxicity study of a systemic fungicide: artea 330 EC on the physiology and the respiratory metabolism of the tadpole (Rana saharica). | 2007 |
|
| Bioaccumulation and biotransformation of chiral triazole fungicides in rainbow trout (Oncorhynchus mykiss). | 2006-12-30 |
|
| Comparison of lanosterol-14 alpha-demethylase (CYP51) of human and Candida albicans for inhibition by different antifungal azoles. | 2006-11-10 |
|
| Fungicides affect the production of extracellular mucilaginous material (ECMM) and the peripheral growth unit (PGU) in two wood-rotting basidiomycetes. | 2006-10 |
|
| Influence of pH on the stereoselective degradation of the fungicides epoxiconazole and cyproconazole in soils. | 2006-09-01 |
|
| Postulated pathogenic pathway in triazole fungicide induced dysmorphogenic effects. | 2006-08 |
|
| Selection for increased cyproconazole tolerance in Mycosphaerella graminicola through local adaptation and in response to host resistance. | 2006-07 |
|
| [Behaviour azole fungicide and fluconazole in Cryptococcus neoformans clinical and environmental isolates]. | 2006-06-12 |
|
| MgSlt2, a cellular integrity MAP kinase gene of the fungal wheat pathogen Mycosphaerella graminicola, is dispensable for penetration but essential for invasive growth. | 2006-04 |
|
| In vitro selection of an effective fungicide against Armillaria mellea and control of white root rot of grapevine in the field. | 2006-03 |
|
| Determination of 22 triazole compounds including parent fungicides and metabolites in apples, peaches, flour, and water by liquid chromatography/tandem mass spectrometry. | 2006-01-03 |
|
| Effects of two systemic fungicides: Artea (Propiconazole+cyproconazole) and Punch (Flusilazole) on the physiology and the respiratory metabolism of durum wheat (Triticum durum L.). | 2006 |
|
| Determination of azolic fungicides in wine by solid-phase extraction and high-performance liquid chromatography-atmospheric pressure chemical ionization-mass spectrometry. | 2005-05-27 |
|
| Capillary electrophoresis for analyzing pesticides in fruits and vegetables using solid-phase extraction and stir-bar sorptive extraction. | 2005-05-06 |
|
| Application of solid-phase extraction to quantitatively determine cyproconazole and tebuconazole in treated wood using liquid chromatography with UV detection. | 2005-01-21 |
|
| Liquid chromatography-electrospray quadrupole ion-trap mass spectrometry of nine pesticides in fruits. | 2004-09-03 |
|
| Chiral separation of some triazole pesticides by supercritical fluid chromatography. | 2004-08-13 |
|
| Evaluation of a method based on liquid chromatography/electrospray tandem mass spectrometry for analyzing eight triazolic and pyrimidine fungicides in extracts of processed fruits and vegetables. | 2004-08-07 |
|
| Multiple mechanisms account for variation in base-line sensitivity to azole fungicides in field isolates of Mycosphaerella graminicola. | 2003-12 |
|
| Triazole fungicide degradation in peaches in the field and in model systems. | 2003-04 |
|
| Molecular cloning and characterisation of three new ATP-binding cassette transporter genes from the wheat pathogen Mycosphaerella graminicola. | 2002-05-01 |
|
| High-performance chiral separation of fourteen triazole fungicides by sulfated beta-cyclodextrin-mediated capillary electrophoresis. | 2001-03-30 |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 22:12:47 GMT 2025
by
admin
on
Mon Mar 31 22:12:47 GMT 2025
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| Record UNII |
622B9C3E6T
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| Record Status |
Validated (UNII)
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| Record Version |
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EPA PESTICIDE CODE |
128993
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DTXSID0032601
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m4038
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622B9C3E6T
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cyproconazole
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300000053296
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Cyproconazole
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