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
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.
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.
ID Source | ID |
---|---|
PubMed CID | 86132 |
CHEMBL ID | 2131954 |
CHEBI ID | 83748 |
SCHEMBL ID | 20791 |
MeSH ID | M0246878 |
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 |
Cyproconazole is a representative and widely used triazole fungicide with four stereoisomers. It will bring some risks to non-target organisms.
Excerpt | Reference | Relevance |
---|---|---|
"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 |
Excerpt | Reference | Relevance |
---|---|---|
"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 |
Excerpt | Relevance | Reference |
---|---|---|
" 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 |
Class | Description |
---|---|
monochlorobenzenes | Any member of the class of chlorobenzenes containing a mono- or poly-substituted benzene ring in which only one substituent is chlorine. |
tertiary alcohol | A 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. |
triazoles | An azole in which the five-membered heterocyclic aromatic skeleton contains three N atoms and two C atoms. |
cyclopropanes | Cyclopropane 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 | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
---|---|---|---|---|---|---|---|
pregnane X receptor | Rattus norvegicus (Norway rat) | Potency | 31.6228 | 0.0251 | 27.9203 | 501.1870 | AID651751 |
GLI family zinc finger 3 | Homo sapiens (human) | Potency | 41.7964 | 0.0007 | 14.5928 | 83.7951 | AID1259369; AID1259392 |
AR protein | Homo sapiens (human) | Potency | 47.6095 | 0.0002 | 21.2231 | 8,912.5098 | AID1259247; AID743063 |
progesterone receptor | Homo sapiens (human) | Potency | 48.2616 | 0.0004 | 17.9460 | 75.1148 | AID1346795 |
glucocorticoid receptor [Homo sapiens] | Homo sapiens (human) | Potency | 48.6728 | 0.0002 | 14.3764 | 60.0339 | AID720691 |
pregnane X nuclear receptor | Homo sapiens (human) | Potency | 27.1395 | 0.0054 | 28.0263 | 1,258.9301 | AID1346982 |
estrogen nuclear receptor alpha | Homo sapiens (human) | Potency | 32.4476 | 0.0002 | 29.3054 | 16,493.5996 | AID743069; AID743075; AID743077; AID743079; AID743080 |
cytochrome P450, family 19, subfamily A, polypeptide 1, isoform CRA_a | Homo sapiens (human) | Potency | 24.1881 | 0.0017 | 23.8393 | 78.1014 | AID743083 |
nuclear factor erythroid 2-related factor 2 isoform 1 | Homo sapiens (human) | Potency | 0.0022 | 0.0006 | 27.2152 | 1,122.0200 | AID651741 |
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] |
Assay ID | Title | Year | Journal | Article |
---|---|---|---|---|
AID1112888 | Fungicidal activity against Oculimacula yallundae assessed as inhibition of mycelial growth in presence of 10 g glucose incubated at 19 degC in dark for 4 weeks | 2013 | Pest management science, Jan, Volume: 69, Issue:1 | Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae. |
AID1112877 | Resistance 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 assay | 2013 | Pest management science, Jan, Volume: 69, Issue:1 | Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae. |
AID1112872 | Resistance 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 assay | 2013 | Pest management science, Jan, Volume: 69, Issue:1 | Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae. |
AID1112895 | Resistance 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 assay | 2013 | Pest management science, Jan, Volume: 69, Issue:1 | Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae. |
AID1112881 | Resistance 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 assay | 2013 | Pest management science, Jan, Volume: 69, Issue:1 | Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae. |
AID1112885 | Resistance 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 assay | 2013 | Pest management science, Jan, Volume: 69, Issue:1 | Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae. |
AID1112879 | Resistance 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 assay | 2013 | Pest management science, Jan, Volume: 69, Issue:1 | Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae. |
AID1112894 | Resistance 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 assay | 2013 | Pest management science, Jan, Volume: 69, Issue:1 | Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae. |
AID1112871 | Resistance 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 assay | 2013 | Pest management science, Jan, Volume: 69, Issue:1 | Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae. |
AID1112878 | Resistance 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 assay | 2013 | Pest management science, Jan, Volume: 69, Issue:1 | Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae. |
AID1112887 | Selectivity index, ratio of EC50 for Oculimacula acuformis to EC50 for Oculimacula yallundae in presence of 10 g glucose by mycelial growth inhibition assay | 2013 | Pest management science, Jan, Volume: 69, Issue:1 | Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae. |
AID1112893 | Resistance 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 assay | 2013 | Pest management science, Jan, Volume: 69, Issue:1 | Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae. |
AID1112875 | Fungicidal activity against prochloraz-susceptible Oculimacula yallundae isolate ProS assessed as inhibition of germ tube elongation incubated at 19 degC in dark for 48 hr | 2013 | Pest management science, Jan, Volume: 69, Issue:1 | Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae. |
AID1112880 | Resistance 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 assay | 2013 | Pest management science, Jan, Volume: 69, Issue:1 | Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae. |
AID1112890 | Selectivity index, ratio of EC50 for Oculimacula acuformis to EC50 for Oculimacula yallundae by germ tube elongation inhibition assay | 2013 | Pest management science, Jan, Volume: 69, Issue:1 | Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae. |
AID1112882 | Resistance 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 assay | 2013 | Pest management science, Jan, Volume: 69, Issue:1 | Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae. |
AID1112891 | Fungicidal activity against Oculimacula yallundae assessed as inhibition of germ tube elongation incubated at 19 degC in dark for 48 hr | 2013 | Pest management science, Jan, Volume: 69, Issue:1 | Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae. |
AID1112892 | Fungicidal activity against Oculimacula acuformis assessed as inhibition of germ tube elongation incubated at 19 degC in dark for 48 hr | 2013 | Pest management science, Jan, Volume: 69, Issue:1 | Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae. |
AID1112889 | Fungicidal activity against Oculimacula acuformis assessed as inhibition of mycelial growth in presence of 10 g glucose incubated at 19 degC in dark for 4 weeks | 2013 | Pest 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] |
Timeframe | Studies, This Drug (%) | All Drugs % |
---|---|---|
pre-1990 | 0 (0.00) | 18.7374 |
1990's | 1 (2.04) | 18.2507 |
2000's | 15 (30.61) | 29.6817 |
2010's | 21 (42.86) | 24.3611 |
2020's | 12 (24.49) | 2.80 |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |
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.
| This Compound (48.09) All Compounds (24.57) |
Publication Type | This drug (%) | All Drugs (%) |
---|---|---|
Trials | 0 (0.00%) | 5.53% |
Reviews | 1 (2.00%) | 6.00% |
Case Studies | 0 (0.00%) | 4.05% |
Observational | 0 (0.00%) | 0.25% |
Other | 49 (98.00%) | 84.16% |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |