Cyproconazole
(Synonyms: 环唑醇) 目录号 : GC30173
A triazole fungicide
Cas No.:94361-06-5
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Cyproconazole is a triazole fungicide.1 It reduces mycelial growth of A. mellea on grapevine roots. Cyproconazole also reduces defoliation of rose plants induced by the plant pathogenic fungus D. rosae.2 It is lethal to the freshwater invertebrates C. riparius and D. tigrina (LC50s = 17.46 and 47.38 mg/L, respectively, in tank water).3 Cyproconazole induces liver hypertrophy and fat vacuolation, as well as induces hepatocellular adenoma and carcinoma formation, in mice.4
1.Aguín, O., Mansilla, J.P., and Sainz, M.J.In vitro selection of an effective fungicide against Armillaria mellea and control of white root rot of grapevine in the fieldPest. Manag. Sci.62(3)223-228(2006) 2.Bowen, K.L., and Roark, R.S.Management of black spot of rose with winter fungicide treatmentPlant Dis.85(4)393-398(2001) 3.Saraiva, A.S., Sarmento, R.A., Golovko, O., et al.Lethal and sub-lethal effects of cyproconazole on freshwater organisms: A case study with Chironomus riparius and Dugesia tigrinaEnviron. Sci. Pollut. Res. Int.25(12)12169-12176(2018) 4.Peffer, R.C., Moggs, J.G., Pastoor, T., et al.Mouse liver effects of cyproconazole, a triazole fungicide: Role of the constitutive androstane receptorToxicol. Sci.99(1)315-325(2007)
| Cas No. | 94361-06-5 | SDF | |
| 别名 | 环唑醇 | ||
| Canonical SMILES | ClC1=CC=C(C(C(C)C2CC2)(O)CN3N=CN=C3)C=C1 | ||
| 分子式 | C15H18ClN3O | 分子量 | 291.78 |
| 溶解度 | DMSO : ≥ 34 mg/mL (116.53 mM) | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 3.4272 mL | 17.1362 mL | 34.2724 mL |
| 5 mM | 0.6854 mL | 3.4272 mL | 6.8545 mL |
| 10 mM | 0.3427 mL | 1.7136 mL | 3.4272 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Stereoselective in vitro metabolism of Cyproconazole in rat liver microsomes and identification of major metabolites
Chemosphere 2021 Feb;264(Pt 2):128495.33038739 10.1016/j.chemosphere.2020.128495
The vast usage of agrochemicals enhances food security globally but may pose challenge to understand the risk assessment to non-target organisms and human beings, and liver microsomes are responsible for metabolism of these agrochemicals in vivo. In this study, stereoselective metabolism of chiral triazole fungicide Cyproconazole in rat liver microsomes has been investigated through chiral LC-MS/MS technique. The half-lives of four Cyproconazole stereoisomers were different ranging from 95 to 187 min, and (2S, 3R)-cyproconazole preferentially metabolized in rat liver microsomes. In addition, the results from metabolism kinetic study indicated that rat liver microsomes showed the stronger potency to deplete (2S, 3R)-cyproconazole than the others. Then, homology modeling and molecular docking results revealed that the docking energy between (2S, 3R)-cyproconazole and the cytochrome P450 CYP3A1 (-7.46 kcal⋅mol-1) was higher than the others, meaning that (2S, 3R)-cyproconazole exhibited the strongest binding ability to this enzyme. Moreover, two main metabolites of Cyproconazole coming from hydroxylation and dehydration were observed, and possible metabolic reactions of Cyproconazole in rat liver microsomes were identified through using an LCQ ion trap mass spectrometer. This kind of systematic metabolic investigation of Cyproconazole at chiral level would provide valuable information for ecological and human health risk assessment of chiral pesticides.
Enantioselective toxic effects of Cyproconazole enantiomers against Rana nigromaculata
Environ Pollut 2018 Dec;243(Pt B):1825-1832.30408870 10.1016/j.envpol.2018.09.060
The environmental contaminant, especially pesticides, threatened the amphibian population. In this assay, the enantioselective behavior of Cyproconazole on Rana nigromaculata was studied. We found LC50 (lethal concentration causing 50% mortality) of 4-enantiomers was nearly twice as 3-enantiomers in 96 h acute toxicity test. Besides, the significant considerable variation of oxidative stress and LDH (lactic dehydrogenase) induced by the four enantiomers indicated that Cyproconazole could enantioselectively affect enzymes in tadpoles. Bioaccumulation experiments showed the order of Cyproconazole in the tadpoles was 4-enantiomers>3- enantiomers>2- enantiomers>1- enantiomers during the exposure for 28d. In tissue distribution test, Cyproconazole was formed and accumulated in order of 4-enantiomers>2-enantiomers>3- enantiomers>1- enantiomers, except that in the gut. During the elimination experiment, Cyproconazole was rapidly eliminated by 95% within the only 24 h. These results suggested that the influence of enantioselective behavior should consider when assessing ecological risk of chiral pesticides to amphibians.
Crystal structure of Cyproconazole
Acta Crystallogr E Crystallogr Commun 2015 Nov 28;71(Pt 12):o1007.26870467 PMC4719948
The title compound [systematic name: 2-(4-chloro-phen-yl)-3-cyclo-propyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol], C15H18ClN3O, is a conazole fungicide. The asymmetric unit comprises two enanti-omeric pairs (mol-ecules A and B) in which the dihedral angles between the chloro-phenyl and triazole rings are 46.54 (9) (mol-ecule A) and 67.03 (8)° (mol-ecule B). In the crystal, C-H⋯O, O-H⋯N and C-H⋯Cl hydrogen bonds and weak C-H⋯π inter-actions [3.473 (2) Å] link adjacent mol-ecules, forming columns along the a axis.
Hepatotoxic effects of Cyproconazole and prochloraz in wild-type and hCAR/hPXR mice
Arch Toxicol 2017 Aug;91(8):2895-2907.28058446 10.1007/s00204-016-1925-2
The agricultural fungicides Cyproconazole and prochloraz exhibit hepatotoxicity in rodent studies and are tumorigenic following chronic exposure. Both substances are suspected to act via a CAR (constitutive androstane receptor)/PXR (pregnane-X-receptor)-dependent mechanism. Human relevance of these findings is under debate. A 28-day toxicity study was conducted in mice with humanized CAR and PXR (hCAR/hPXR) with two dose levels (50 or 500 ppm) of both substances, using the model CAR activator phenobarbital as a reference. Results were compared to wild-type mice. A treatment-related increase in liver weights was observed for all three substances at least at the high-dose level. Changes in the expression of classic CAR/PXR target genes such as Cyp2b10 were induced by Cyproconazole and phenobarbital in both genotypes, while prochloraz treatment resulted in gene expression changes indicative of additional aryl hydrocarbon receptor activation, e.g. by up-regulation of Cyp1a1 expression. Cyproconazole-induced effects on CAR-dependent gene expression, liver weight, and hepatic lipid accumulation were more prominent in wild-type mice, where significant genotype differences were observed at the high-dose level. Moreover, high-dose cyproconazole-treated mice from the wild-type group responded with a marked increase in hepatocellular proliferation, while hCAR/hPXR mice did not. In conclusion, our data demonstrate that Cyproconazole and PB induce CAR/PXR downstream effects in hepatocytes in vivo via both, the murine and human receptors. At high doses of Cyproconazole, however, the responses were clearly more pronounced in wild-type mice, indicating increased sensitivity of rodents to CAR agonist-induced effects in hepatocytes.
Developmental toxicity of the triazole fungicide Cyproconazole in embryo-larval stages of zebrafish (Danio rerio)
Environ Sci Pollut Res Int 2019 Feb;26(5):4913-4923.30569354 10.1007/s11356-018-3957-z
Cyproconazole is a triazole fungicide used to protect a diverse range of fruits, vegetables, and grain crops. As such, it has the potential to enter aquatic environments and affect non-target organisms. The objective of this study was to assess the acute toxicity of the triazole fungicide Cyproconazole to zebrafish embryos by assessing mortality, developmental defects, morphological abnormality, oxidative respiration, and locomotor activity following a 96-h exposure. Zebrafish embryos at 6-h post-fertilization (hpf) were exposed to either a solvent control (0.1% DMSO, v/v), or one dose of 10, 25, 50, 100, 250, and 500 μM Cyproconazole for 96 h. Data indicated that Cyproconazole exhibited low toxicity to zebrafish embryos, with a 96-h LC50 value of 90.6 μM (~ 26.4 mg/L). Zebrafish embryos/larvae displayed a significant decrease in spontaneous movement, hatching rate, and heartbeats/20 s with 50, 100, and 250 μM Cyproconazole exposure. Malformations (i.e., pericardial edema, yolk sac edema, tail deformation, and spine deformation) were also detected in zebrafish exposed to ≿50 μM Cyproconazole, with significant increases in cumulative deformity rate at 48, 72, and 96 hpf. In addition, a 20-30% decrease in basal and oligomycin-induced ATP respiration was observed after 24-h exposure to 500 μM Cyproconazole in embryos. To determine if Cyproconazole affected locomotor activity, a dark photokinesis assay was conducted in larvae following 7-day exposure to 1, 10, and 25 μM Cyproconazole in two independent trials. Activity in the dark period was decreased for zebrafish exposed to 25 μM Cyproconazole in the first trial, and hypoactivity was also observed in zebrafish exposed to 1 μM Cyproconazole in a second trial, suggesting that Cyproconazole can affect locomotor activity. These data improve understanding of the toxicity of Cyproconazole in developing zebrafish and contribute to environmental risk assessments for the triazole fungicides on aquatic organisms. We report that, based on the overall endpoints assessed, Cyproconazole exhibits low risk for developing fish embryos, as many effects were observed above environmentally-relevant levels.