Page last updated: 2024-12-07

cyproconazole

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Cyproconazole is a triazole fungicide widely used in agriculture to control a broad spectrum of fungal diseases in various crops. It is synthesized via a multi-step process involving the reaction of 1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone with 2-chloro-1,3-thiazole. Cyproconazole inhibits the biosynthesis of ergosterol, an essential component of fungal cell membranes, leading to disruption of fungal cell function and ultimately, fungal growth. Its broad-spectrum activity makes it effective against powdery mildew, rust, and other fungal diseases. Research on cyproconazole focuses on its efficacy, mode of action, environmental fate, and potential resistance development in fungi. Its importance lies in its contribution to crop protection and ensuring food security. Studies are conducted to optimize its application, minimize environmental impact, and develop alternative fungicides to counter resistance.'

cyproconazole: inhibits ergosterol biosynthesis in fungi [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

cyproconazole : A diastereoisomeric mixture composed of the enantiomeric pair (2R,3S)- and (2S,3R)-cyproconazole in ratio 1:1 with the enantiomeric pair (2R,3R)- and (2S,3S)-cyproconazole. A broad spectrum fungicide, it is used on cereals and other field crops used to control Septoria, rust, powdery mildew and other diseases. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol : A tertiary alcohol that is butan-2-ol substituted by a 4-chlorophenyl group at position 2, a cyclopropyl group at position 3 and a 1H-1,2,4-triazol-1-yl group at position 1. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID86132
CHEMBL ID2131954
CHEBI ID83748
SCHEMBL ID20791
MeSH IDM0246878

Synonyms (57)

Synonym
hsdb 7706
unii-622b9c3e6t
622b9c3e6t ,
NCGC00163963-01
cyproconazole [iso]
alto
atemi
sentinel turf fungicide
1h-1,2,4-triazole-1-ethanol, alpha-(4-chlorophenyl)-alpha-(1-cyclopropylethyl)-
atemi c
alpha-(4-chlorophenyl)-alpha-(1-cyclopropylethyl)-1h-1,2,4-triazole-1-ethanol
alto 100sl
san 619f
sn 108266
94361-06-5
2-(4-chlorophenyl)-3-cyclopropyl-1-(1h-1,2,4-triazol-1-yl)butan-2-ol
cyproconazole
NCGC00163963-02
2-(4-chlorophenyl)-3-cyclopropyl-1-(1,2,4-triazol-1-yl)butan-2-ol
san-619f
NCGC00163963-03
C18456
dtxsid0032601 ,
tox21_301185
dtxcid8012601
NCGC00255083-01
cas-94361-06-5
chebi:83748 ,
CHEMBL2131954
FT-0642271
cyproconazol
AKOS015907652
cyproconazole [mi]
sn-108266
bonanza
paindor
cyproconazole [hsdb]
1h-1,2,4-triazole-1-ethanol, .alpha.-(4-chlorophenyl)-.alpha.-(1-cyclopropylethyl)-
.alpha.-(4-chlorophenyl)-.alpha.-(1-cyclopropylethyl)-1h-1,2,4- triazole-1-ethanol
sentinel
SCHEMBL20791
CS-5833
HY-A0277
mfcd01678672
113096-99-4
cyproconazol, pestanal(r), analytical standard
cyproconazole 100 microg/ml in cyclohexane
cyproconazole 10 microg/ml in acetonitrile
cyproconazol, certified reference material, tracecert(r)
cyproconazol isomer 2
cyproconazol isomer 1
Q27157173
Z2065617652
AS-14696
cyproconazole 1000 microg/ml in acetone
2-(4-chlorophenyl)-3-cyclopropyl-2-(1h-1,2,4-triazol-1-yl)butan-1-ol
EN300-22833606

Research Excerpts

Overview

Cyproconazole is a representative and widely used triazole fungicide with four stereoisomers. It will bring some risks to non-target organisms.

ExcerptReferenceRelevance
"Cyproconazole is a representative and widely used triazole fungicide with four stereoisomers, which will bring some risks to non-target organisms. "( Stereoselective bioaccumulation and dissipation of four stereoisomers of cyproconazole in earthworm-soil microcosm.
Cang, T; Di, S; Li, Y; Liu, Z; Qi, P; Wang, X; Wang, Z; Xu, L; Zhao, H, 2024
)
3.12

Toxicity

ExcerptReferenceRelevance
"The toxicological relevance of effects observed at molecular stage, which occur at dose levels well below classical no-observed adverse effect levels is currently subject to controversial scientific debate."( Hepatotoxic effects of (tri)azole fungicides in a broad dose range.
Haider, W; Heise, T; Knebel, C; Kneuer, C; Marx-Stoelting, P; Niemann, L; Pfeil, R; Rieke, S; Schmidt, F, 2015
)
0.42

Dosage Studied

ExcerptRelevanceReference
" For EE2 a dose-response relationship was established with EC50 = 60."( Testing estrogenicity of known and novel (xeno-)estrogens in the MolDarT using developing zebrafish (Danio rerio).
Eggen, RI; Junghans, M; Muncke, J, 2007
)
0.34
"To clarify the dose-response relationship between constitutive androstane receptor (CAR) activity and induction of cytochrome P450 2B (CYP2B) expression and hypertrophy by triazole fungicides in mouse liver, three dose levels of cyproconazole (Cypro), tebuconazole (Teb), fluconazole (Flu), and phenobarbital (PB), a typical CYP2B inducer, were administrated in diet to male wild-type (WT) and CAR-knockout (CARKO) mice for one week."( Dose-response involvement of constitutive androstane receptor in mouse liver hypertrophy induced by triazole fungicides.
Inoue, K; Irie, K; Kodama, Y; Matsuo, S; Nishikawa, A; Ozawa, S; Takahashi, M; Tamura, K; Yoshida, M, 2013
)
0.57
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (4)

ClassDescription
monochlorobenzenesAny member of the class of chlorobenzenes containing a mono- or poly-substituted benzene ring in which only one substituent is chlorine.
tertiary alcoholA tertiary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has three other carbon atoms attached to it.
triazolesAn azole in which the five-membered heterocyclic aromatic skeleton contains three N atoms and two C atoms.
cyclopropanesCyclopropane and its derivatives formed by substitution.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (9)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
pregnane X receptorRattus norvegicus (Norway rat)Potency31.62280.025127.9203501.1870AID651751
GLI family zinc finger 3Homo sapiens (human)Potency41.79640.000714.592883.7951AID1259369; AID1259392
AR proteinHomo sapiens (human)Potency47.60950.000221.22318,912.5098AID1259247; AID743063
progesterone receptorHomo sapiens (human)Potency48.26160.000417.946075.1148AID1346795
glucocorticoid receptor [Homo sapiens]Homo sapiens (human)Potency48.67280.000214.376460.0339AID720691
pregnane X nuclear receptorHomo sapiens (human)Potency27.13950.005428.02631,258.9301AID1346982
estrogen nuclear receptor alphaHomo sapiens (human)Potency32.44760.000229.305416,493.5996AID743069; AID743075; AID743077; AID743079; AID743080
cytochrome P450, family 19, subfamily A, polypeptide 1, isoform CRA_aHomo sapiens (human)Potency24.18810.001723.839378.1014AID743083
nuclear factor erythroid 2-related factor 2 isoform 1Homo sapiens (human)Potency0.00220.000627.21521,122.0200AID651741
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (19)

Assay IDTitleYearJournalArticle
AID1112888Fungicidal activity against Oculimacula yallundae assessed as inhibition of mycelial growth in presence of 10 g glucose incubated at 19 degC in dark for 4 weeks2013Pest management science, Jan, Volume: 69, Issue:1
Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae.
AID1112877Resistance index, ratio of EC50 for sterol 14alpha-demethylation inhibitor-resistant Oculimacula yallundae MDR to EC50 for sterol 14alpha-demethylation inhibitor-resistant Oculimacula yallundae TriR1 by germ tube elongation assay2013Pest management science, Jan, Volume: 69, Issue:1
Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae.
AID1112872Resistance index, ratio of EC50 for prochloraz-resistant Oculimacula yallundae isolate ProR1 to EC50 for prochloraz-susceptible Oculimacula yallundae isolate ProS by germ tube elongation inhibition assay2013Pest management science, Jan, Volume: 69, Issue:1
Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae.
AID1112895Resistance index, ratio of EC50 for sterol 14alpha-demethylation inhibitor-resistant Oculimacula yallundae MDR to EC50 for wild type Oculimacula yallundae TriS by mycelial growth inhibition assay2013Pest management science, Jan, Volume: 69, Issue:1
Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae.
AID1112881Resistance index, ratio of EC50 for sterol 14alpha-demethylation inhibitor-resistant Oculimacula yallundae TriR1 to EC50 for wild type Oculimacula yallundae TriS by germ tube elongation assay2013Pest management science, Jan, Volume: 69, Issue:1
Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae.
AID1112885Resistance index, ratio of EC50 for sterol 14alpha-demethylation inhibitor-resistant Oculimacula yallundae TriR1 to EC50 for wild type Oculimacula yallundae TriS by mycelial growth inhibition assay2013Pest management science, Jan, Volume: 69, Issue:1
Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae.
AID1112879Resistance index, ratio of EC50 for sterol 14alpha-demethylation inhibitor-resistant Oculimacula yallundae TriR2 to EC50 for sterol 14alpha-demethylation inhibitor-resistant Oculimacula yallundae TriR1 by germ tube elongation assay2013Pest management science, Jan, Volume: 69, Issue:1
Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae.
AID1112894Resistance index, ratio of EC50 for sterol 14alpha-demethylation inhibitor-resistant Oculimacula yallundae TriR2 to EC50 for sterol 14alpha-demethylation inhibitor-resistant Oculimacula yallundae TriR1 by mycelial growth inhibition assay2013Pest management science, Jan, Volume: 69, Issue:1
Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae.
AID1112871Resistance index, ratio of EC50 for prochloraz-resistant Oculimacula yallundae isolate ProR2 to EC50 for prochloraz-susceptible Oculimacula yallundae isolate ProS by germ tube elongation inhibition assay2013Pest management science, Jan, Volume: 69, Issue:1
Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae.
AID1112878Resistance index, ratio of EC50 for sterol 14alpha-demethylation inhibitor-resistant Oculimacula yallundae MDR to EC50 for wild type Oculimacula yallundae TriS by germ tube elongation assay2013Pest management science, Jan, Volume: 69, Issue:1
Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae.
AID1112887Selectivity index, ratio of EC50 for Oculimacula acuformis to EC50 for Oculimacula yallundae in presence of 10 g glucose by mycelial growth inhibition assay2013Pest management science, Jan, Volume: 69, Issue:1
Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae.
AID1112893Resistance index, ratio of EC50 for sterol 14alpha-demethylation inhibitor-resistant Oculimacula yallundae TriR2 to EC50 for wild type Oculimacula yallundae TriS by mycelial growth inhibition assay2013Pest management science, Jan, Volume: 69, Issue:1
Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae.
AID1112875Fungicidal activity against prochloraz-susceptible Oculimacula yallundae isolate ProS assessed as inhibition of germ tube elongation incubated at 19 degC in dark for 48 hr2013Pest management science, Jan, Volume: 69, Issue:1
Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae.
AID1112880Resistance index, ratio of EC50 for sterol 14alpha-demethylation inhibitor-resistant Oculimacula yallundae TriR2 to EC50 for wild type Oculimacula yallundae TriS by germ tube elongation assay2013Pest management science, Jan, Volume: 69, Issue:1
Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae.
AID1112890Selectivity index, ratio of EC50 for Oculimacula acuformis to EC50 for Oculimacula yallundae by germ tube elongation inhibition assay2013Pest management science, Jan, Volume: 69, Issue:1
Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae.
AID1112882Resistance index, ratio of EC50 for sterol 14alpha-demethylation inhibitor-resistant Oculimacula yallundae MDR to EC50 for sterol 14alpha-demethylation inhibitor-resistant Oculimacula yallundae TriR1 by mycelial growth inhibition assay2013Pest management science, Jan, Volume: 69, Issue:1
Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae.
AID1112891Fungicidal activity against Oculimacula yallundae assessed as inhibition of germ tube elongation incubated at 19 degC in dark for 48 hr2013Pest management science, Jan, Volume: 69, Issue:1
Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae.
AID1112892Fungicidal activity against Oculimacula acuformis assessed as inhibition of germ tube elongation incubated at 19 degC in dark for 48 hr2013Pest management science, Jan, Volume: 69, Issue:1
Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae.
AID1112889Fungicidal activity against Oculimacula acuformis assessed as inhibition of mycelial growth in presence of 10 g glucose incubated at 19 degC in dark for 4 weeks2013Pest management science, Jan, Volume: 69, Issue:1
Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (49)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (2.04)18.2507
2000's15 (30.61)29.6817
2010's21 (42.86)24.3611
2020's12 (24.49)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 48.09

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index48.09 (24.57)
Research Supply Index3.93 (2.92)
Research Growth Index5.84 (4.65)
Search Engine Demand Index74.68 (26.88)
Search Engine Supply Index2.12 (0.95)

This Compound (48.09)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (2.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other49 (98.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]