Home>>Signaling Pathways>> Microbiology & Virology>> Fungal>>Triadimenol

Triadimenol Sale

(Synonyms: 三唑醇) 目录号 : GC45079

A metabolite of triadimefon

Triadimenol Chemical Structure

Cas No.:55219-65-3

规格 价格 库存 购买数量
250mg
¥839.00
现货
500mg
¥1,593.00
现货

电话:400-920-5774 Email: sales@glpbio.cn

Customer Reviews

Based on customer reviews.

Sample solution is provided at 25 µL, 10mM.

产品文档

Quality Control & SDS

View current batch:

产品描述

Triadimenol is a metabolite of triadimefon , a broad-spectrum chiral triazole fungicide, that is formed by reduction of a carbonyl group to the corresponding alcohol. It is teratogenic, inducing cranial nerve and ganglia abnormalities in a rat post-implantation whole embryo culture model when used at concentrations ranging from 12.5 to 125 μM. In vivo, triadimenol induces embryotoxicity in rats and rabbits when administered orally at doses of 100 and 40 mg/kg, respectively. Embryonic exposure to triadimenol (3-3,000 μg/L) induces embryonic mortality as well as decreases fertility and increases the number of female offspring in medaka fish (O. latipes).

Chemical Properties

Cas No. 55219-65-3 SDF
别名 三唑醇
Canonical SMILES ClC1=CC=C(OC(N2N=CN=C2)C(O)C(C)(C)C)C=C1
分子式 C14H18ClN3O2 分子量 295.8
溶解度 Methanol: 25 mg/ml 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。
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。

溶解性数据

制备储备液
1 mg 5 mg 10 mg
1 mM 3.3807 mL 16.9033 mL 33.8066 mL
5 mM 0.6761 mL 3.3807 mL 6.7613 mL
10 mM 0.3381 mL 1.6903 mL 3.3807 mL
  • 摩尔浓度计算器

  • 稀释计算器

  • 分子量计算器

质量
=
浓度
x
体积
x
分子量
 
 
 
*在配置溶液时,请务必参考产品标签上、MSDS / COA(可在Glpbio的产品页面获得)批次特异的分子量使用本工具。

计算

动物体内配方计算器 (澄清溶液)

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
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

Research Update

Stereoselective degradation and microbial epimerization of Triadimenol in soils

Chirality 2013 Jun;25(6):355-60.PMID:23661341DOI:10.1002/chir.22175.

Triadimenol is a widely used triazole fungicide and consists of four stereoisomers with 1R,2S, 1S,2R, 1R,2R, and 1S,2S configurations. The trans-enantiomeric pair (1R,2S-isomer and 1S,2R-isomer) is also called triadimenol-A and the cis-enantiomeric pair (1R,2R-isomer and 1S,2S-isomer) triadimenol-B. In this study, the stereoselective degradation and chiral stability of Triadimenol in two soils were investigated in details. The dissipation of technical Triadimenol, a 6:1 mixture of triadimenol-A and triadimenol-B, showed significant epimerization from triadimenol-A to triadimenol-B occurred along with the dissipation process. The degradation exhibited some stereoselectivity, resulting in a concentration order of 1S,2S > 1R,2R > 1R,2S > 1S,2R or 1S,2S > 1R,2R > 1S,2R > 1R,2S at the end of the 100 days incubation for Baoding soil or Wuhan soil, respectively. Further incubation of triadimenol-B revealed no epimerization, i.e. triadimenol-B was configurationally stable in soil, and 1R,2R-triadimenol degraded slightly slower in the former part and slightly faster in the later part of the incubation than 1S,2S-triadimenol. Moreover, by incubation of enantiopure 1S,2R-triadimenol and 1R,2S-triadimenol, the results documented the epimerization for each enantiomer occurred at both C-1 and C-2 positions. Finally, the present work also documented that the enantiomerization reaction for all the four stereoisomers was nearly negligible in the soils.

Triadimenol promotes the production of reactive oxygen species and apoptosis with cardiotoxicity and developmental abnormalities in zebrafish

Sci Total Environ 2023 Mar 1;862:160761.PMID:36502969DOI:10.1016/j.scitotenv.2022.160761.

Various types of fungicides, especially triazole fungicides, are used to prevent fungal diseases on farmlands. However, the developmental toxicity of one of the triazole fungicides, Triadimenol, remains unclear. Therefore, we used the zebrafish animal model, a representative toxicological model, to investigate it. Triadimenol induced morphological alterations in the eyes and body length along with yolk sac and heart edema. It also stimulated the production of reactive oxygen species and expression of inflammation-related genes and caused apoptosis in the anterior regions of zebrafish, especially in the heart. The phosphorylation levels of Akt, ERK, JNK, and p38 proteins involved in the PI3K and MAPK pathways, which are important for the development process, were also reduced by Triadimenol. These changes led to malformation of the heart and vascular structures, as observed in the flk1:eGFP transgenic zebrafish models and a reduction in the heart rate. In addition, the expression of genes associated with cardiac and vascular development was also reduced. Therefore, we elucidated the mechanisms associated with Triadimenol toxicity that leads to various abnormalities and developmental toxicity in zebrafish.

Chronic exposure to Triadimenol at environmentally relevant concentration adversely affects aging biomarkers in Caenorhabditis elegans associated with insulin/IGF-1 signaling pathway

Sci Total Environ 2018 Nov 1;640-641:485-492.PMID:29864662DOI:10.1016/j.scitotenv.2018.05.314.

Triadimenol, an agricultural fungicide, is an emerging environmental concern due to its wide usage, detection in the environment, and its chemical persistency. Triadimenol has been found to disrupt endocrine signaling and alter function of several transcription factors, yet its age-related toxicity effects remain unclear. This study used Caenorhabditis elegans as an in vivo model organism to elucidate the age-related effects of Triadimenol and its underlying mechanisms. The results showed that chronic exposure to Triadimenol at environmentally relevant concentrations (3, 30, and 300 μg/L) adversely affected several toxicity endpoints including growth, total brood size, and locomotive behaviors. In addition, Triadimenol (300 μg/L) significantly reduced the mean lifespan of wild-type N2 C. elegans from 17.9 to 16 days. Chronic exposure to Triadimenol (300 μg/L) also significantly affected age-related behavioral changes, with a decreased pharyngeal pumping rate and an increased defecation cycle. Moreover, an increased accumulation of aging biomarkers including lipofuscin, lipid peroxidation, and reactive oxygen species (H2O2 and O2-) level upon chronic Triadimenol exposure was observed in aged worms. Furthermore, chronic Triadimenol exposure increased the transcriptional factor DAF-16 nuclear localization. Finally, mutation of daf-2, age-1, pdk-1, akt-1, or akt-2 restored the accumulation of lipofuscin in aged worms upon chronic Triadimenol exposure, while mutation of daf-16 led to more enhanced lipofuscin accumulation. Therefore, the insulin/IGF-1 signaling pathway may serve as an important molecular basis for Triadimenol induced aging declines in C. elegans.

Developmental exposures to an azole fungicide Triadimenol at environmentally relevant concentrations cause reproductive dysfunction in females of medaka fish

Chemosphere 2016 Jun;152:181-9.PMID:26971170DOI:10.1016/j.chemosphere.2016.02.078.

Triadimenol is an effective meatabolite derived from the triazole fungicide triadimenfon. It is an agriculturally important reagent of environmentally emerging concern because of its broad use, persistent occurrence in the environment and greater fungicidal or toxic potency than the parent compound. However, the ecotoxicological impact of Triadimenol on fish populations remains unclear. In this study, we investigated developmental toxicity and endocrine disruption effects in medaka fish (Oryzias latipes) exposed at an early life stage to Triadimenol. First, mortality, gross development and oxidative stress responses were assessed with Triadimenol exposure (3-3000 μg/L) during the embryonic stage. Then, medaka at a sensitive stage of early sexual development underwent 35-day continuous chronic exposure to Triadimenol, and the endocrine disruption effects were assessed in adulthood and the next generation. Embryonic exposure to Triadimenol did not induce significant teratogenic effects or oxidative stress in embryos or hatchlings. However, early-life exposure to Triadimenol under environmentally relevant concentrations (3-30 μg/L) and 300 μg/L persistently altered ovary development and reproduction in female adults and skewed the sex ratio in progeny. As well, Triadimenol exposure interrupted the hormone balance, as seen by the expression of genes responsible for estrogen metabolism and egg reproduction. Environmentally relevant Triadimenol exposure in medaka fish at early life stages may have ecotoxicological impact in aquatic environments. Along with previous studies, we suggest that conazoles share similar modes of action in disrupting hormone homeostasis and reproduction in fish and mammals.

Stereoselective metabolism, distribution, and bioaccumulation brof triadimefon and Triadimenol in lizards

Ecotoxicol Environ Saf 2014 Sep;107:276-83.PMID:25011125DOI:10.1016/j.ecoenv.2014.06.021.

In this research, Chinese lizards (Eremias argus) were chosen as laboratory animal to evaluate the stereoselectivity in the processes of metabolism, distribution, and bioaccumulation of triadimefon. A validated chiral high-performance liquid chromatography coupled with triple quadruple mass spectrometry (HPLC-MS/MS) method was developed for determining enantiomers' residues of parent compound triadimefon and its metabolite Triadimenol in lizard blood and tissues. Pharmacokinetic results of single-does exposure suggested that S-(+)-triadimefon was metabolized easier than R-(-)-triadimefon, and RR-(+)-triadimenol was the main metabolic product of triadimefon. During the continuous exposure of two dose (40mg/kg(bw)·d and 200mg/kg(bw)·d), enantiomers of triadimefon and Triadimenol were detected in all body compartments, with the highest triadimefon concentrations in brain. However, the Triadimenol concentrations were not significantly different among the compartments. The concentrations of RS-(+)-triadimenol were negative correlated with concentrations of RR-(+)-triadimenol both in blood (r=-0.775, p=0.024) and liver (r=-0.834, p=0.02) in 200mg/kg(bw)·d group, which indicates that chiral conversion between enantiomers of Triadimenol might exist in the metabolic process of triadimefon. In all the processes, the enantiomer fractions (EFs) of R-(-)-triadimefon and RR-(+)-triadimenol were significantly different from their natural ratios, 0.5 and 0.1, respectively, which proved that metabolism, bioaccumulation, and distribution of triadimefon and Triadimenol in lizards were enantioselective. These results help enrich and supplement the knowledge of the stereoselective behaviour of triadimefon and Triadimenol in reptile.