Fenpropimorph
(Synonyms: 顺-4-叔丁基苯基(-2-甲基丙基)-2,6-二甲基吗啉) 目录号 : GC47339A fungicide that inhibits the sterol pathway
Cas No.:67564-91-4
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Fenpropimorph is a fungicide that inhibits the sterol pathway.1 It inhibits δ8-δ7-sterol isomerase in yeast at low concentrations, with δ14-sterol reductase being blocked at higher levels, preventing the biosynthesis of ergosterol .2 Fenpropimorph is also able to inhibit sterol synthesis in certain plants and mammalian cells.1,3
1.Costet, M.F., Achouri, M.E., Charlet, M., et al.Ecdysteroid biosynthesis and embryonic development are disturbed in insects (Locusta migratoria) reared on plant diet (Triticum sativum) with a selectively modified sterol profileProc. Natl. Acad. Sci. USA84(3)643-647(1987) 2.Marcireau, C., Guilloton, M., and Karst, F.In vivo effects of fenpropimorph on the yeast Saccharomyces cerevisiae and determination of the molecular basis of the antifungal propertyAntimicrob. Agents Chemother.34(6)989-993(1990) 3.Corio-Costet, M.F., Gerst, N., Benveniste, P., et al.Inhibition by the fungicide fenpropimorph of cholesterol biosynthesis in 3T3 fibroblastsBiochem J.256(3)829-834(1988)
| Cas No. | 67564-91-4 | SDF | |
| 别名 | 顺-4-叔丁基苯基(-2-甲基丙基)-2,6-二甲基吗啉 | ||
| Canonical SMILES | CC(CC1=CC=C(C(C)(C)C)C=C1)CN2C[C@@H](C)O[C@@H](C)C2 | ||
| 分子式 | C20H33NO | 分子量 | 303.5 |
| 溶解度 | DMF: 15 mg/ml,DMSO: 5 mg/ml,Ethanol: 15 mg/ml,Ethanol:PBS (pH 7.2)(1:2): 0.3 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。 |
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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 | 3.2949 mL | 16.4745 mL | 32.9489 mL |
| 5 mM | 0.659 mL | 3.2949 mL | 6.5898 mL |
| 10 mM | 0.3295 mL | 1.6474 mL | 3.2949 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。
Simultaneous Analysis of Fenpropimorph and Fenpropimorph Acid in Six Different Livestock Products Using a Single-Sample Preparation Method Followed by Liquid Chromatography-Tandem Mass Spectrometry
Molecules 2021 Sep 24;26(19):5791.PMID:34641333DOI:10.3390/molecules26195791.
Pesticides in livestock products must be measured to ensure food safety. We developed a single-sample preparation method followed by liquid chromatography-tandem mass spectrometry (LC-MS/MS) for simultaneous determination of Fenpropimorph and Fenpropimorph acid in six different livestock products. The extraction method was a modification of the quick, easy, cheap, effective, rugged, and safe (QuEChERS) method and was validated according to the CODEX guidelines. The matrix-matched calibration curves for Fenpropimorph and Fenpropimorph acid exhibited good linearity, with coefficients of determination (R2 values) higher than 0.998. The limit of detection (LOD) and the limit of quantitation (LOQ) were 1.25 and 5.0 µg kg-1, respectively. The average recovery values ranged from 61.5% to 97.1% for samples fortified to the LOQ, 2 × LOQ, and 10 × LOQ. The method fully complied with the CODEX guidelines and was successfully applied to real samples obtained from domestic markets.
Reprotoxic effects of Fenpropimorph on the fertilizing potential of AI boars: A case study
Reprod Domest Anim 2022 Mar;57(3):337-340.PMID:34863004DOI:10.1111/rda.14062.
This case study describes the effects of a contamination of boar bedding material with reprotoxic compounds in an AI centre in southern Germany. The origin of the investigations was an extreme decline in the production output of the boars. In July 2021, more than 54% of boars were not in production and over 45% of ejaculates had insufficient sperm quality and quantity, which is a significant drop in comparison with the other months. This drop was accompanied by oligozoospermia (azoospermia), asthenozoospermia and teratozoospermia. Through intensive troubleshooting, the changes could be attributed to Fenpropimorph, an ergosterol biosynthesis-inhibiting fungicide with reprotoxic potential, which was found in the sawdust used as bedding as well as in liver samples of affected animals, reaching a concentration (mean ± SD) between 0.20 ± 0.36 mg/kg and 0.019 ± 0.001 mg/kg respectively. Furthermore, autopsy findings revealed hyperaemia of the testis, histologically focal degeneration of the germinal epithelium and signs of reduced spermatogenesis and spermiogenesis.
Fenpropimorph slows down the sterol pathway and the development of the arbuscular mycorrhizal fungus Glomus intraradices
Mycorrhiza 2009 Aug;19(6):365-374.PMID:19340463DOI:10.1007/s00572-009-0238-1.
The direct impact of Fenpropimorph on the sterol biosynthesis pathway of Glomus intraradices when extraradical mycelia alone are in contact with the fungicide was investigated using monoxenic cultures. Bi-compartmental Petri plates allowed culture of mycorrhizal chicory roots in a compartment without Fenpropimorph and exposure of extraradical hyphae to the presence of increasing concentrations of Fenpropimorph (0, 0.02, 0.2, 2, 20 mg l(-1)). In the fungal compartment, sporulation, hyphal growth, and fungal biomass were already reduced at the lowest fungicide concentration. A decrease in total sterols, in addition to an increase in the amount of squalene and no accumulation of abnormal sterols, suggests that the sterol pathway is severely slowed down or that squalene epoxidase was inhibited by Fenpropimorph in G. intraradices. In the root compartment, neither extraradical and intraradical development of the arbuscular mycorrhizal (AM) fungus nor root growth was affected when they were not in direct contact with the fungicide; only hyphal length was significantly affected at 2 mg l(-1) of Fenpropimorph. Our results clearly demonstrate a direct impact of Fenpropimorph on the AM fungus by a perturbation of its sterol metabolism.
Fenpropimorph affects uptake of uracil and cytosine in Saccharomyces cerevisiae
Antimicrob Agents Chemother 1994 May;38(5):1004-7.PMID:8067730DOI:10.1128/AAC.38.5.1004.
Fenpropimorph was shown to inhibit the accumulation of the pyrimidine bases uracil and cytosine from the growth media in Saccharomyces cerevisiae. Uracil prototrophs of S. cerevisiae were more resistant to the growth-inhibitory effects of Fenpropimorph than were uracil auxotrophs. High concentrations of uracil rescued fenpropimorph-treated uracil auxotrophs, and cytosine, which is accumulated by a separate mechanism, could also support growth of treated uracil auxotrophs. Fenpropimorph caused a significant decrease in the uptake of radiolabeled uracil, which was not due to accumulation of ergosta-8,14-dienol (ignosterol) in the treated cultures. Radiolabeled cytosine uptake was unaffected by drug treatment in a wild-type strain but was inhibited in a sterol mutant, in which ergosterol was absent from the cell. The role of Fenpropimorph in causing membrane dysfunction through a mechanism other than altered sterol metabolism is discussed.
The small molecule Fenpropimorph rapidly converts chloroplast membrane lipids to triacylglycerols in Chlamydomonas reinhardtii
Front Microbiol 2015 Feb 24;6:54.PMID:25759683DOI:10.3389/fmicb.2015.00054.
Concern about global warming has prompted an intense interest in developing economical methods of producing biofuels. Microalgae provide a promising platform for biofuel production, because they accumulate high levels of lipids, and do not compete with food or feed sources. However, current methods of producing algal oil involve subjecting the microalgae to stress conditions, such as nitrogen deprivation, and are prohibitively expensive. Here, we report that the fungicide Fenpropimorph rapidly causes high levels of neutral lipids to accumulate in Chlamydomonas reinhardtii cells. When treated with Fenpropimorph (10 μg mL(-1)) for 1 h, Chlamydomonas cells accumulated at least fourfold the amount of triacylglycerols (TAGs) present in the untreated control cells. Furthermore, the quantity of TAGs present after 1 h of Fenpropimorph treatment was over twofold higher than that formed after 9 days of nitrogen starvation in medium with no acetate supplement. Biochemical analysis of lipids revealed that the accumulated TAGs were derived mainly from chloroplast polar membrane lipids. Such a conversion of chloroplast polar lipids to TAGs is desirable for biodiesel production, because polar lipids are usually removed during the biodiesel production process. Thus, our data exemplified that a cost and time effective method of producing TAGs is possible using Fenpropimorph or similar drugs.