Tebuconazole
(Synonyms: 戊唑醇) 目录号 : GC32160
A triazole fungicide
Cas No.:107534-96-3
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
Tebuconazole is a triazole fungicide that is active against both seed and foliar fungi.1 It inhibits 14α-demethylase isolated from U. maydis and S. bicolor with IC50 values of 0.05 and 0.16 nM, respectively.2 It inhibits the androgenic effect of the androgen receptor agonist DHT (IC20 = 2.89 ?M) and is cytotoxic (EC20 = 38.9 ?M) in an MDA-kb2 assay.3 Tebuconazole (50 and 100 mg/kg per day) administered during gestation reduces testosterone levels and increases testicular levels of progesterone and 17α-hydroxyprogesterone in male rat fetuses.4 It has a feminizing effect on male pups and a virilizing effect on female pups. When administered to rats gestationally through postnatal day 42, tebuconazole (20 and 60 mg/kg per day) leads to cell death of pyramidal cells in the CA3-4 region of the hippocampus and layer V of the cortex concomitant with impairment in learning the platform location in the Morris water maze.5
1.Reinecke, P., Kaspers, H., Scheinpflug, H., et al.BAY HWG 1608, a new fungicide for foliar spray and seed-treatment use against a wide spectrum of fungal pathogensBr. Crop Prot. Conf.--Pests Dis., Proc.141-46(1986) 2.Zarn, J.A., Brüschweiler, B.J., and Schlatter, J.R.Azole fungicides affect mammalian steroidogenesis by inhibiting sterol 14 α-demethylase and aromataseEnviron. Health Perspect.111(3)255-261(2003) 3.Orton, F., Rosivatz, E., Scholze, M., et al.Widely used pesticides with previously unknown endocrine activity revealed as in vitro antiandrogensEnviron. Health Perspect.119(6)794-800(2011) 4.Taxvig, C., Hass, U., Axelstad, M., et al.Endocrine-disrupting activities in vivo of the fungicides tebuconazole and epoxiconazoleToxicol. Sci.100(2)464-473(2007) 5.Moser, V.C., Barone, S., Jr., Smialowicz, R.J., et al.The effects of perinatal tebuconazole exposure on adult neurological, immunological, and reproductive function in ratsToxicol. Sci.62(2)339-352(2001)
| Cas No. | 107534-96-3 | SDF | |
| 别名 | 戊唑醇 | ||
| Canonical SMILES | CC(C)(C)C(O)(CCC1=CC=C(Cl)C=C1)CN2C=NC=N2 | ||
| 分子式 | C16H22ClN3O | 分子量 | 307.82 |
| 溶解度 | DMSO : ≥ 50 mg/mL (162.43 mM);Water : < 0.1 mg/mL (insoluble) | 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 | 3.2487 mL | 16.2433 mL | 32.4865 mL |
| 5 mM | 0.6497 mL | 3.2487 mL | 6.4973 mL |
| 10 mM | 0.3249 mL | 1.6243 mL | 3.2487 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。
Effects of Tebuconazole Application on Soil Microbiota and Enzymes
Molecules 2022 Nov 3;27(21):7501.PMID:36364328DOI:10.3390/molecules27217501.
Identification of pesticide impact on the soil microbiome is of the utmost significance today. Diagnosing the response of bacteria to Tebuconazole, used for plant protection, may help isolate the most active bacteria applicable in the bioaugmentation of soils contaminated with this preparation. Bearing in mind the above, a study was undertaken to test the effect of Tebuconazole on the diversity of bacteria at all taxonomic levels and on the activity of soil enzymes. It was conducted by means of standard and metagenomic methods. Its results showed that Tebuconazole applied in doses falling within the ranges of good agricultural practice did not significantly disturb the biological homeostasis of soil and did not diminish its fertility. Tebuconazole was found to stimulate the proliferation of organotrophic bacteria and fungi, and also the activities of soil enzymes responsible for phosphorus, sulfur, and carbon metabolism. It did not impair the activity of urease responsible for urea hydrolysis, or cause any significant changes in the structure of bacterial communities. All analyzed soil samples were mainly populated by bacteria from the phylum Proteobacteria, Actinobacteria, Firmicutes, Gemmatimonadetes, Acidobacteria, Planctomycetes, and Chloroflexi. Bacteria from the genera Kaistobacter, Arthrobacter, and Streptomyces predominated in the soils contaminated with Tebuconazole, whereas these from the Gemmata genus were inactivated by this preparation.
Residue behavior and risk assessment of pyraclostrobin and Tebuconazole in peppers under different growing conditions
Environ Sci Pollut Res Int 2022 Dec;29(56):84096-84105.PMID:36264460DOI:10.1007/s11356-022-23469-9.
This study evaluates the residue behavior and risks of pyraclostrobin and Tebuconazole in peppers. An analytical method for the simultaneous determination of the concentration of these fungicides in peppers was developed using ultra-high performance liquid chromatography-triple quadrupole mass spectrometry. Pepper samples were extracted with acetonitrile and cleaned with primary secondary amine and graphitized carbon black. The average recoveries of pyraclostrobin and Tebuconazole under three fortification levels were 86.7-101.4% and 81.7-104.4%, with relative standard deviations of 4.0-7.2% and 3.8-10.9%, respectively. The limit of quantification of both fungicides in peppers was 0.01 mg/kg. The terminal residue trial of 30% pyraclostrobin and Tebuconazole suspension concentrate was investigated for samples cultivated in open fields and greenhouses. The results showed that the terminal residues of pyraclostrobin and Tebuconazole in peppers were lower than the maximum residue limits established by GB 2763-2021 (0.5 mg/kg for pyraclostrobin and 2 mg/kg for Tebuconazole). The results of a statistical t-test indicated that there was no significant difference between samples grown in open fields and greenhouses. According to the international estimate of short-term intake (IESTI) calculation model, provided by the Joint FAO/WHO Meeting on Pesticide Residues, the acute dietary exposure risk of both fungicides in peppers was acceptable for the general population, with an IESTI of 0-3% and 0-5% of the acute reference dose for pyraclostrobin and Tebuconazole, respectively.
Tebuconazole induces liver injury coupled with ROS-mediated hepatic metabolism disorder
Ecotoxicol Environ Saf 2021 Sep 1;220:112309.PMID:34015629DOI:10.1016/j.ecoenv.2021.112309.
Tebuconazole, the most widely used fungicide, is reported to cause various environmental problems and have serious health risks in humans. Despite numerous advances in toxicity studies, its internal metabolic process and the underlying mechanisms have not been systemically studied. The present study administered low doses (0.02 g/kg bw and 0.06 g/kg bw) of Tebuconazole to C57BL/6 mice in vivo. The high performance liquid chromatography-tandem mass spectrometry (HPLC-MS/MS) was developed and validated to analyze the Tebuconazole in different organs, and our data revealed that Tebuconazole mainly accumulated in the liver and that histopathological damage were exhibited in this organ. Tebuconazole significantly dysregulated phase ⅿ and phase II-metabolizing enzymes, ATP-binding cassette (ABC) efflux transporters (Abcc2 and Abcc3) and fatty acid metabolism-related genes (Cdkn1a and Fasn), thereby directly causing liver hypertrophy and steatosis. Importantly, the excessive induction of reactive oxygen species (ROS) and oxidative stress partially accounted for the metabolic abnormalities mediated by Tebuconazole. Moreover, these alterations were related to the abnormal transcriptional levels of peroxisome proliferator-activated receptor α (PPAR-α) and liver x receptor α (LXR-α), which were predicted to bind to Tebuconazole via hydrogen bonding interactions. The current findings provide new insight into the molecular mechanisms of metabolic abnormalities induced by Tebuconazole at low concentration, and are conducive to a better understanding of the environmental risk posed by this fungicide.
A common fungicide Tebuconazole promotes colitis in mice via regulating gut microbiota
Environ Pollut 2022 Jan 1;292(Pt B):118477.PMID:34763016DOI:10.1016/j.envpol.2021.118477.
As a common fungicide, Tebuconazole are ubiquitous in the natural environment and poses many potential risks. In this study, we examined the effects of exposure to Tebuconazole on colitis in mice and explored its underlying mechanism. Specifically, exposure to Tebuconazole could cause structural damage and inflammatory cell infiltration in colon tissue, activate the expression of inflammation-related genes, disrupt the expression of barrier function-related genes, and induce the colonic inflammation in mice. Similarly, exposure to Tebuconazole could also exacerbate DSS-induced colitis in mice. In addition, we found that Tebuconazole also could change the composition of the gut microbiota. In particular, Tebuconazole significantly increases the relative abundance of Akkermansia of mice. Moreover, Tebuconazole resulted in metabolic profiles disorders of the serum, leading to significant changes in the relative contents of metabolites involving glycolipid metabolism and amino acid metabolism. Particularly, the results of the gut microbiota transplantation experiment showed that exposure to Tebuconazole could induced colonic inflammation in mice in a gut microbiota-dependent manner. Taken together, these results indicated that Tebuconazole could induce colitis in mice via regulating gut microbiota. Our findings strongly support the concept that the gut microbiota is a key trigger of inflammatory bowel disease caused by pesticide intake.
Tebuconazole induced cardiotoxicity in male adult rat
Food Chem Toxicol 2020 Mar;137:111134.PMID:32006631DOI:10.1016/j.fct.2020.111134.
Tebuconazole is an effective systemic fungicide that belongs to the triazoles family. It has been widely used in both agricultural and medical sectors for the control of fungal diseases. Although TEB poses serious threats to mammals health, studies regarding its cardiotoxicity are very limited. Thus, we aimed to evaluate the effects of TEB on some biochemical parameters, the induction of apoptosis and DNA damage in the heart tissue. Male Wistar rats were treated with TEB at varied oral doses for 28 consecutive days. This study demonstrates that TEB decreased cardiac acetylcholinesterase, increased serum marker enzymes such as creatinine phosphokinase (CPK) and lactate dehydrogenase (LDH), and altered the lipid profile by increasing serum levels of total cholesterol (T-CHOL), triglyceride (TG), low-density lipoprotein cholesterol (LDL-C) and reduced high-density lipoprotein cholesterol (HDL-C) levels. Furthermore, TEB increased levels of p53 and Bax/Bcl2 ratio, released the cytochrome c into the cytosol and activated caspase-9 and caspase-3. Besides, our results showed that TEB induced genotoxic effects. TEB induced DNA fragmentation and increased the frequency of micronucleated bone marrow cells. Moreover, TEB treatment developed fibrosis in the myocardium. Our results suggest that TEB exposure may affect myocardial cells normal functioning and triggers apoptosis.