Imazalil (Enilconazole)
(Synonyms: 抑霉唑; Enilconazole) 目录号 : GC32111
An imidazole fungicide
Cas No.:35554-44-0
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Imazalil is an imidazole fungicide that inhibits ergosterol biosynthesis.1 Imazalil inhibits the growth of various fungi in vitro including P. italicum, A. niger, U. maydis, B. alii, and C. cucumerinum in a pH-dependent manner (MICs = 0.005-2 μg/ml at pH 7).2 It inhibits S. cerevisiae, but not rat liver microsomal, cytochrome P450 enzymes (CYPs; IC50s = 0.088 and 80 μM, respectively), as well as aromatase CYP19 from human placental microsomes (IC50 = 0.34 μM).1,3 Imazalil activates the murine pregnane X receptor (PXR) in a concentration-dependent manner in a cell-based reporter assay.4 It increases hepatic CYP3A11 and CYP2B10 mRNA levels in mice when administered at a dose of 100 mg/kg. Imazalil also increases Ki-67-positive nuclei in liver sections and hepatic MCM2 mRNA levels, markers of cell proliferation, in mice when co-administered with the murine constitutive androstane receptor (mCAR) agonist TCPOBOP . Formulations containing imazalil have been used to control fungal infection in agriculture.
1.Vanden Bossche, H., Lauwers, W., Willemsens, G., et al.Molecular basis for the antimycotic and antibacterial activity of N-substituted imidazoles and triazoles: The inhibition of isoprenoid biosynthesisPestic. Sci.15(2)188-198(1984) 2.Siegel, M.R., Kerkenaar, A., and Kaars Sijpesteijn, A.Antifungal activity of the systemic fungicide imazalilNeth. J. Pl. Path.83(Suppl. 1)121-133(1977) 3.Vinggaard, A.M., Hnida, C., Breinholt, V., et al.Screening of selected pesticides for inhibition of CYP19 aromatase activity in vitroToxicol. In Vitro14(3)227-234(2000) 4.Yoshimaru, S., Shizu, R., Tsuruta, S., et al.Acceleration of murine hepatocyte proliferation by imazalil through the activation of nuclear receptor PXRJ. Toxicol. Sci.43(7)443-450(2018)
| Cas No. | 35554-44-0 | SDF | |
| 别名 | 抑霉唑; Enilconazole | ||
| Canonical SMILES | C=CCOC(C1=CC=C(Cl)C=C1Cl)CN2C=CN=C2 | ||
| 分子式 | C14H14Cl2N2O | 分子量 | 297.18 |
| 溶解度 | DMSO : ≥ 100 mg/mL (336.50 mM);Water : 20 mg/mL (67.30 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 | 3.365 mL | 16.8248 mL | 33.6496 mL |
| 5 mM | 0.673 mL | 3.365 mL | 6.7299 mL |
| 10 mM | 0.3365 mL | 1.6825 mL | 3.365 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。
Dermatophytosis in cats: ABCD guidelines on prevention and management
J Feline Med Surg2013 Jul;15(7):598-604.PMID:23813824DOI:10.1177/1098612X13489222.
Overview: Dermatophytosis, usually caused by Microsporum canis, is the most common fungal infection in cats worldwide, and one of the most important infectious skin diseases in this species. Many adult cats are asymptomatic carriers. Severe clinical signs are seen mostly in kittens or immunosuppressed adults. Poor hygiene is a predisposing factor, and the disease may be endemic in shelters or catteries. Humans may be easily infected and develop a similar skin disease. Infection: Infectious arthrospores produced by dermatophytes may survive in the environment for about a year. They are transmitted through contact with sick cats or healthy carriers, but also on dust particles, brushes, clothes and other fomites. Disease signs: Circular alopecia, desquamation and sometimes an erythematous margin around central healing ('ringworm') are typical. In many cats this is a self-limiting disease with hair loss and scaling only. In immunosuppressed animals, the outcome may be a multifocal or generalised skin disease. Diagnosis: Wood's lamp examination and microscopic detection of arthrospores on hairs are simple methods to confirm M canis infection, but their sensitivity is relatively low. The gold standard for detection is culture on Sabouraud agar of hairs and scales collected from new lesions. Disease management: In shelters and catteries eradication is difficult. Essential is a combination of systemic and topical treatments, maintained for several weeks. For systemic therapy itraconazole is the drug of choice, terbinafine an alternative. Recommended topical treatment is repeated body rinse with an Enilconazole solution or miconazole with or without chlorhexidine. In catteries/shelters medication must be accompanied by intensive decontamination of the environment. Vaccination: Few efficacy studies on anti-M canis vaccines (prophylactic or therapeutic) for cats have been published, and a safe and efficient vaccine is not available.
Efficacy of pomades containing different percentages of Enilconazole in the treatment of bovine dermatophytosis
Vet Dermatol2016 Jun;27(3):181-e45.PMID:26990840DOI:10.1111/vde.12299.
Background: Enilconazole is a broad-spectrum topical antimycotic agent used for the management of bovine dermatophytosis. Hypothesis/objectives: To investigate the efficacy of pomades containing different concentrations of Enilconazole for the treatment of bovine dermatophytosis. Methods: Dermatophytosis was confirmed in 120 cattle from farm in Gole region of Turkey. Animals were divided into six groups (n = 20 in each). Pomades containing 1%, 2%, 3%, 4% and 5% Enilconazole were applied topically to individual lesions in groups I-V, respectively, once a day for 3 days. Group VI animals were used as a control group. Animals were monitored clinically once a week for a two month period. Results: Cows treated with pomades containing 4% and 5% Enilconazole recovered; adverse topical reactions occurred in 40% and 55% of animals, respectively. The success rate for cows treated with pomades containing 3% Enilconazole was 95% and they recovered with no adverse reactions. Success rates for treatment were 25% and 50% for cows treated with pomades containing 1% and 2% Enilconazole, respectively. No improvement was observed in the control group. Conclusions and clinical importance: Pomades containing 3% Enilconazole are recommended for the treatment of bovine dermatophytosis.
Monitoring the behavior of Imazalil and its metabolite in grapes, apples, and the processing of fruit wine at enantiomeric level
J Sci Food Agric2021 Oct;101(13):5478-5486.PMID:33682082DOI:10.1002/jsfa.11196.
Background: Imazalil is widely used in agriculture, which may pose a threat to food safety. This study aimed to investigate the fate of Imazalil and its main metabolite, R14821 (imazalil-M), in field grapes and apples, and in the processing of fruit wine at the enantiomeric level. Results: Analysis method was established to determine Imazalil and imazalil-M enantiomers in grape, apple, fruit wine and pomace. The method showed acceptable recoveries of 71.6-99.9% and precision with relative standard deviation of 0.3-11.7%. Processing factors (PFs) were 0.15-0.40 (for Imazalil enantiomers) and <0.13-0.83 (for imazalil-M enantiomers) during the wine-making process. The PFs after individual steps including washing, peeling, fermentation, and clarification were all less than 1. No enantioselective dissipation of Imazalil was found in grapes under field conditions with half-lives of 23.82-24.49 days. R-(-)-imazalil degraded slightly faster than S-(+)-imazalil in apples under field conditions with half-lives of 9.82-10.09 days. S-(+)-imazalil-M preferentially degraded in field grapes and apple. No significant enantioselectivity of Imazalil and imazalil-M was observed during the wine-making process. The enantiomeric fraction (EF) values of Imazalil were 0.484-0.511 and 0.509-0.522 in grape wine and cider, respectively. The EFs were 0.484-0.501(in grape wine) and 0.484-0.504 (in cider) for imazalil-M. Conclusion: The results showed that the wine-making process could reduce Imazalil and imazalil-M residues in grapes and apples. The finding of non-enantioselectivity of Imazalil during the processing of fruit wine was useful for accurate risk assessment for Imazalil in raw and processing fruits. © 2021 Society of Chemical Industry.
On the terrestrial toxicity of the fungicide Imazalil (Enilconazole) to the earthworm species Eisenia foetida
Ecotoxicol Environ Saf1989 Dec;18(3):313-20.PMID:2612423DOI:10.1016/0147-6513(89)90025-0.
The toxicity of Imazalil (Enilconazole), of its sulfate salt, and of a principal environmental transformation product to the earthworm species Eisenia foetida was determined. The 48-hr contact test and the 14-day artificial soil test as described by OECD guideline 207 were carried out. Concentrations of the parent substance in earthworm tissues at the end of the exposure in soil were determined by gas chromatography. The LC50 of imazalil was 12.8 micrograms/cm2 in the contact test and 541 micrograms/g in the artificial soil test. The LC50 values of the sulfate salt were 11.6 micrograms/cm2 and 532 micrograms/g, respectively. The transformation product had a LC50 of 108 micrograms/cm2 in the contact test, and the survival in the soil test exceeded 90%, even at levels of 1000 micrograms/g. Tissue levels of imazalil in surviving worms were always lower than the concentrations in corresponding soil. The LC50 values largely exceeded the levels expected after normal use. Therefore, the fungicide is not considered to be harmful to earthworms in the soil environment.
Separation of Enilconazole enantiomers in capillary electrophoresis with cyclodextrin-type chiral selectors and investigation of structure of selector-selectand complexes by using nuclear magnetic resonance spectroscopy
Electrophoresis2017 Aug;38(15):1851-1859.PMID:28328068DOI:10.1002/elps.201700078.
In the present study, the enantiomer migration order (EMO) of Enilconazole in the presence of various cyclodextrins (CDs) was investigated by capillary electrophoresis (CE). Opposite EMO of Enilconazole were observed when β-CD or the sulfated heptakis(2-O-methyl-3,6-di-O-sulfo)-β-CD (HMDS-β-CD) was used as the chiral selectors. Nuclear magnetic resonance (NMR) spectroscopy was used to study the mechanism of chiral recognition between Enilconazole enantiomers and those two cyclodextrins. On the basis of rotating frame nuclear Overhauser (ROESY) experiments, the structure of an inclusion complex between Enilconazole and β-CD was derived, in which (+)-enilconazole seemed to form a tighter complex than the (-)-enantiomer. This correlates well with the migration order of Enilconazole enantiomers observed in CE. No evidence of complexation between Enilconazole and HMDS-β-CD could be gathered due to lack of intermolecular nuclear Overhauser effect (NOE). Most likely the interaction between Enilconazole and HMDS-β-CD leads to formation of a shallow external complex that is sufficient for separation of enantiomers in CE but cannot be evidenced based on ROESY experiment. Thus, in this particular case CE documents the presence of intermolecular interactions which are at least very difficult to be evidenced by other instrumental techniques.