Cyproconazole
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Basic Info
| Common Name | Cyproconazole(F05403) |
| 2D Structure | |
| Description | Cyproconazole formula 360 SL is a water-based wood preservative that prevents decay from fungi in above-ground applications. It is not intended to protect wood that is in contact with the ground. Where there is the potential for insect attack, a registered insecticide should also be used. |
| FRCD ID | F05403 |
| CAS Number | 94361-06-5 |
| PubChem CID | 86132 |
| Formula | C15H18ClN3O |
| IUPAC Name | 2-(4-chlorophenyl)-3-cyclopropyl-1-(1,2,4-triazol-1-yl)butan-2-ol |
| InChI Key | UFNOUKDBUJZYDE-UHFFFAOYSA-N |
| InChI | 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 |
| Canonical SMILES | CC(C1CC1)C(CN2C=NC=N2)(C3=CC=C(C=C3)Cl)O |
| Isomeric SMILES | CC(C1CC1)C(CN2C=NC=N2)(C3=CC=C(C=C3)Cl)O |
| Synonyms |
Cyproconazole
94361-06-5
2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol
Alto
Cyproconazol
Atemi
Atemi C
Cyproconazole [ISO]
Alto 100SL
SAN 619F
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Phenylpropanes |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Phenylpropanes |
| Alternative Parents | |
| Molecular Framework | Aromatic heteromonocyclic compounds |
| Substituents | Phenylpropane - Chlorobenzene - Halobenzene - Aryl chloride - Aryl halide - Heteroaromatic compound - Azole - Tertiary alcohol - 1,2,4-triazole - Organoheterocyclic compound - Azacycle - Hydrocarbon derivative - Organic nitrogen compound - Organooxygen compound - Organonitrogen compound - Organochloride - Organohalogen compound - Alcohol - Organopnictogen compound - Organic oxygen compound - Aromatic alcohol - Aromatic heteromonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 291.779 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 5 |
| Complexity | 331 |
| Monoisotopic Mass | 291.114 |
| Exact Mass | 291.114 |
| XLogP | 2.9 |
| Formal Charge | 0 |
| Heavy Atom Count | 20 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 2 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.8890 |
| Human Intestinal Absorption | HIA+ | 0.9960 |
| Caco-2 Permeability | Caco2+ | 0.5660 |
| P-glycoprotein Substrate | Substrate | 0.5293 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8779 |
| Non-inhibitor | 0.8077 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.5261 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.7420 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.6559 |
| CYP450 2D6 Substrate | Non-substrate | 0.8573 |
| CYP450 3A4 Substrate | Substrate | 0.5381 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.7126 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.7144 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8571 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.6189 |
| CYP450 3A4 Inhibitor | Inhibitor | 0.5807 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.7597 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.7837 |
| Non-inhibitor | 0.7678 | |
| AMES Toxicity | Non AMES toxic | 0.5908 |
| Carcinogens | Non-carcinogens | 0.7406 |
| Fish Toxicity | High FHMT | 0.9673 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9133 |
| Honey Bee Toxicity | Low HBT | 0.8836 |
| Biodegradation | Not ready biodegradable | 1.0000 |
| Acute Oral Toxicity | III | 0.7934 |
| Carcinogenicity (Three-class) | Non-required | 0.4965 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.8559 | LogS |
| Caco-2 Permeability | 1.0941 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.4250 | LD50, mol/kg |
| Fish Toxicity | 1.3440 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.4784 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Wild terrestrial vertebrate animals (Feathered wild game, Furred wild game, Kangaroos,) | 1070000 | European Union | 0.05* | 06/02/2018 | |
| Peas | Japan | 0.05ppm | |||
| Terrestrial invertebrate animals (Earthworms, Insects, Snails, Other terrestrial invertebrate animals, Other edible snails not belonging to the genus Helix,) | 1060000 | European Union | 0.05* | 06/02/2018 | |
| Other Poultry,Eggs | Japan | 0.01ppm | |||
| Chicken,Eggs | Japan | 0.01ppm | |||
| Other Poultry Animals,Edible Offal | Japan | 0.01ppm | |||
| Chicken,Edible Offal | Japan | 0.01ppm | |||
| Other Poultry Animals,Kidney | Japan | 0.01ppm | |||
| Chicken,Kidney | Japan | 0.01ppm | |||
| Other Poultry Animals,Liver | Japan | 0.01ppm | |||
| Chicken,Liver | Japan | 0.01ppm | |||
| Other Poultry Animals,Fat | Japan | 0.01ppm | |||
| Chicken,Fat | Japan | 0.01ppm | |||
| Other Poultry Animals,Muscle | Japan | 0.01ppm | |||
| Chicken,Muscle | Japan | 0.01ppm | |||
| Milk | Japan | 0.01ppm | |||
| Pig,Edible Offal | Japan | 1ppm | |||
| Cattle,Edible Offal | Japan | 1ppm | |||
| Other Terrestrial Mammals,Kidney | Japan | 1ppm | |||
| Pig,Kidney | Japan | 1ppm |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Mimicking of cyproconazole behavior in the presence of Cu and Zn. | Rapid Commun Mass Spectrom | 2017 Dec 15 | 28901039 |
| Enantioselective toxic effects of cyproconazole enantiomers against Chlorella pyrenoidosa. | Chemosphere | 2016 Sep | 27268794 |
| Residues of plant protection products in grey partridge eggs in French cerealecosystems. | Environ Sci Pollut Res Int | 2016 May | 26841780 |
| Multilocus resistance evolution to azole fungicides in fungal plant pathogenpopulations. | Mol Ecol | 2016 Dec | 27859799 |
| Combination effects of azole fungicides in male rats in a broad dose range. | Toxicology | 2016 Apr 29 | 27234313 |
| Azole fungicides disturb intracellular Ca2+ in an additive manner in dopaminergicPC12 cells. | Toxicol Sci | 2013 Aug | 23708404 |
| Environmental fate of fungicides in surface waters of a horticultural-production catchment in southeastern Australia. | Arch Environ Contam Toxicol | 2012 Apr | 22037819 |
| Development of monoclonal immunoassays for the determination of triazolefungicides in fruit juices. | J Agric Food Chem | 2008 Oct 8 | 18783243 |
| Bioaccumulation and biotransformation of chiral triazole fungicides in rainbow trout (Oncorhynchus mykiss). | Aquat Toxicol | 2006 Dec 30 | 17118468 |
| Capillary electrophoresis for analyzing pesticides in fruits and vegetables usingsolid-phase extraction and stir-bar sorptive extraction. | J Chromatogr A | 2005 May 6 | 15909524 |
| Liquid chromatography-electrospray quadrupole ion-trap mass spectrometry of nine pesticides in fruits. | J Chromatogr A | 2004 Sep 3 | 15453417 |
| Evaluation of a method based on liquid chromatography/electrospray tandem massspectrometry for analyzing eight triazolic and pyrimidine fungicides in extracts of processed fruits and vegetables. | J AOAC Int | 2004 Jul-Aug | 15295895 |
| Triazole fungicide degradation in peaches in the field and in model systems. | Food Addit Contam | 2003 Apr | 12775479 |
| Pesticide residues in grapes, wine, and their processing products. | J Agric Food Chem | 2000 Apr | 10775335 |
| Multiresidue determination of 19 fungicides in processed fruits and vegetables bycapillary gas chromatography after gel permeation chromatography. | J AOAC Int | 1999 Sep-Oct | 10513021 |
Targets
- General Function:
- Transmembrane signaling receptor activity
- Specific Function:
- Involved in lymphocyte proliferation and functions as a signal transmitting receptor in lymphocytes, natural killer (NK) cells, and platelets.
- Gene Name:
- CD69
- Uniprot ID:
- Q07108
- Molecular Weight:
- 22559.25 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Steroid hydroxylase activity
- Specific Function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
- Gene Name:
- CYP2C9
- Uniprot ID:
- P11712
- Molecular Weight:
- 55627.365 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Steroid hydroxylase activity
- Specific Function:
- Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
- Gene Name:
- CYP2C19
- Uniprot ID:
- P33261
- Molecular Weight:
- 55930.545 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Steroid hydroxylase activity
- Specific Function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
- Gene Name:
- CYP2C18
- Uniprot ID:
- P33260
- Molecular Weight:
- 55710.075 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- Uniprot ID:
- P05184
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Steroid hydroxylase activity
- Specific Function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
- Gene Name:
- CYP2B6
- Uniprot ID:
- P20813
- Molecular Weight:
- 56277.81 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Sulfotransferase activity
- Specific Function:
- Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfonation of steroids and bile acids in the liver and adrenal glands.
- Gene Name:
- SULT2A1
- Uniprot ID:
- Q06520
- Molecular Weight:
- 33779.57 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Type iii transforming growth factor beta receptor binding
- Specific Function:
- Multifunctional protein that controls proliferation, differentiation and other functions in many cell types. Many cells synthesize TGFB1 and have specific receptors for it. It positively and negatively regulates many other growth factors. It plays an important role in bone remodeling as it is a potent stimulator of osteoblastic bone formation, causing chemotaxis, proliferation and differentiation in committed osteoblasts. Can promote either T-helper 17 cells (Th17) or regulatory T-cells (Treg) lineage differentiation in a concentration-dependent manner. At high concentrations, leads to FOXP3-mediated suppression of RORC and down-regulation of IL-17 expression, favoring Treg cell development. At low concentrations in concert with IL-6 and IL-21, leads to expression of the IL-17 and IL-23 receptors, favoring differentiation to Th17 cells.
- Gene Name:
- TGFB1
- Uniprot ID:
- P01137
- Molecular Weight:
- 44340.685 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Oxygen binding
- Specific Function:
- Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
- Gene Name:
- CYP19A1
- Uniprot ID:
- P11511
- Molecular Weight:
- 57882.48 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Vitamin d 24-hydroxylase activity
- Specific Function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
- Gene Name:
- CYP1A1
- Uniprot ID:
- P04798
- Molecular Weight:
- 58164.815 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Oxygen binding
- Specific Function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
- Gene Name:
- CYP3A5
- Uniprot ID:
- P20815
- Molecular Weight:
- 57108.065 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Steroid binding
- Specific Function:
- UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone. Isoform 2 lacks transferase activity but acts as a negative regulator of isoform 1.
- Gene Name:
- UGT1A1
- Uniprot ID:
- P22309
- Molecular Weight:
- 59590.91 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
- Specific Function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
- Gene Name:
- CYP1A2
- Uniprot ID:
- P05177
- Molecular Weight:
- 58293.76 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Vitamin d3 25-hydroxylase activity
- Specific Function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide (PubMed:11159812). Catalyzes 4-beta-hydroxylation of cholesterol. May catalyze 25-hydroxylation of cholesterol in vitro (PubMed:21576599).
- Gene Name:
- CYP3A4
- Uniprot ID:
- P08684
- Molecular Weight:
- 57342.67 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]