Fludioxonil
(Synonyms: 咯菌腈) 目录号 : GC47361
A fungicide
Cas No.:131341-86-1
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Fludioxonil is a phenylpyrrole fungicide.1 It inhibits the growth of B. cinerea isolates from strawberry and blackberry crops (EC50s = 0.06-0.38 mg/L).2 Fludioxonil also inhibits the growth of S. cerevisiae AF293 and C. albicans IFO1385 in a concentration-dependent manner.1,3 It is an estrogen receptor α (ERα) agonist (EC50 = 3.7 μM in a yeast reporter assay) that induces expression of the oncogenic microRNA miR-21, inhibits estradiol-induced proliferation, and reduces cell motility of MCF-7 breast cancer cells in vitro.4
1.Kim, J.H., Campbell, B.C., Mahoney, N., et al.Enhanced activity of strobilurin and fludioxonil by using berberine and phenolic compounds to target fungal antioxidative stress responseLett. Appl. Microbiol.45(2)134-141(2007) 2.Li, X., FernÁndez-OrtuÑo, D., Grabke, A., et al.Resistance to fludioxonil in Botrytis cinerea isolates from blackberry and strawberryPhytopathology104(7)724-732(2014) 3.Ochiai, N., Fujimura, M., Oshima, M., et al.Effects of iprodione and fludioxonil on glycerol synthesis and hyphal development in Candida albicansBiosci. Biotechnol. Biochem.66(10)2209-2215(2002) 4.Teng, Y., Manavalan, T.T., Hu, C., et al.Endocrine disruptors fludioxonil and fenhexamid stimulate miR-21 expression in breast cancer cellsToxicol. Sci.131(1)71-83(2013)
| Cas No. | 131341-86-1 | SDF | |
| 别名 | 咯菌腈 | ||
| Canonical SMILES | FC1(F)OC2=CC=CC(C3=CNC=C3C#N)=C2O1 | ||
| 分子式 | C12H6F2N2O2 | 分子量 | 248.2 |
| 溶解度 | DMSO : 200 mg/mL (805.83 mM; Need ultrasonic) | 储存条件 | Store at -20°C, filled inert atmosphere |
| 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 | 4.029 mL | 20.145 mL | 40.2901 mL |
| 5 mM | 0.8058 mL | 4.029 mL | 8.058 mL |
| 10 mM | 0.4029 mL | 2.0145 mL | 4.029 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。
Uncertainty surrounding the mechanism and safety of the post-harvest fungicide Fludioxonil
Food Chem Toxicol 2019 Jan;123:561-565.PMID:30458269DOI:10.1016/j.fct.2018.11.037.
Fludioxonil is a phenylpyrrole pesticide that is applied to fruit and vegetable crops post-harvest to minimize losses to mold, both during transport and at point of sale. Its effectiveness is reflected in the dramatic increase in its production/usage since its introduction in 1994, an increase that has peaked in recent years as it became licenced for use abroad. Recently, doubts as to the nature of its mechanism of action have been raised. Given that the pesticide has long been known to induce stress intermediates in target and non-target organisms alike, the lack of a firmly established mechanism might be cause for concern. Troubling reports further delineate a capacity to disrupt hepatic, endocrine and neurological systems, indicating that Fludioxonil may represent a health threat to consumers. In the absence of a clear, safe mechanism of action, Fludioxonil should be re-evaluated for its potential to impact human health.
Inherent tolerance of Colletotrichum gloeosporioides to Fludioxonil
Pestic Biochem Physiol 2021 Feb;172:104767.PMID:33518054DOI:10.1016/j.pestbp.2020.104767.
Colletotrichum spp. cause devastating diseases in agricultural crops, including fruit crops. They can differ in host plant and plant organ specificity and even in fungicide sensitivity. In strawberry, members of the C. gloeosporioides species complex (referred to as C. gloeosporioides) primarily cause crown rot and those of the C. acutatum species complex (referred to as C. acutatum) primarily cause fruit rot. Fludioxonil is registered for use (in combination with cyprodinil; Switch 62.5WG in the US) in strawberry against anthracnose disease caused by Colletotrichum spp. In this study we examined the sensitivity of C. gloeosporioides (C. fructicola and C. siamense) and C. acutatum (C. nymphaeae and C. fioriniae) isolates from different hosts and different geographical locations in the US to Fludioxonil and examined possible mechanisms of inherent fungicide tolerance. The dose response to Fludioxonil of C. gloeosporioides isolates (including 4 isolates of C. theobromicola) revealed about 70% inhibition of mycelial growth at 1 mg/L that was maintained at 10 mg/L and 100 mg/L and lead to minimum inhibitory concentration (MIC) values >100 mg/L. In contrast, mycelial growth of C. acutatum isolates was completely inhibited at 1 mg/L. C. gloeosporioides isolates were also significantly less sensitive to iprodione. An investigation into possible mechanisms of C. gloeosporioides isolates tolerance to Fludioxonil and iprodione revealed no evidence of OS-1 gene involvement. Isolates of both species complexes were equally sensitive to salt stress based on mycelial growth inhibition on potato dextrose agar amended with 2%, 4%, and 6% NaCl. In addition, orthologous amino acid alterations in OS-1 previously linked to Fludioxonil resistance in Botrytis cinerea were not found in C. gloeosporioides or C. acutatum isolates. This study also showed limited in vitro inhibitory activity of cyprodinil against isolates of both species complexes (MIC values >100 mg/L) and unveils a potential weakness of the Fludioxonil+cyprodinil premixture marketed as Switch 62.5WG against C. gloeosporioides species complexes.
Exploring Potential Mechanisms of Fludioxonil Resistance in Fusarium oxysporum f. sp. melonis
J Fungi (Basel) 2022 Aug 11;8(8):839.PMID:36012827DOI:10.3390/jof8080839.
Melon Fusarium wilt (MFW), which is caused by Fusarium oxysporum f. sp. melonis (FOM), is a soil-borne disease that commonly impacts melon cultivation worldwide. In the absence of any disease-resistant melon cultivars, the control of MFW relies heavily on the application of chemical fungicides. Fludioxonil, a phenylpyrrole fungicide, has been shown to have broad-spectrum activity against many crop pathogens. Sensitivity analysis experiments suggest that Fludioxonil has a strong inhibitory effect on the mycelial growth of FOM isolates. Five fludioxonil-resistant FOM mutants were successfully generated by repeated exposure to Fludioxonil under laboratory conditions. Although the mutants exhibited significantly reduced mycelial growth in the presence of the fungicide, there initially appeared to be little fitness cost, with no significant difference (p < 0.05) in the growth rates of the mutants and wild-type isolates. However, further investigation revealed that the sporulation of the fludioxonil-resistant mutants was affected, and mutants exhibited significantly (p < 0.05) reduced growth rates in response to KCl, NaCl, glucose, and mannitol. Meanwhile, molecular analysis of the mutants strongly suggested that the observed Fludioxonil resistance was related to changes in the sequence and expression of the FoOs1 gene. In addition, the current study found no evidence of cross-resistance between Fludioxonil and any of the other fungicides tested. These results indicate that Fludioxonil has great potential as an alternative method of control for FOM in melon crops.
Fludioxonil, a phenylpyrrol pesticide, induces Cytoskeleton disruption, DNA damage and apoptosis via oxidative stress on rat glioma cells
Food Chem Toxicol 2022 Dec;170:113464.PMID:36228901DOI:10.1016/j.fct.2022.113464.
Pesticides products are widely used to increase food productivity and to decrease food-borne diseases. Fludioxonil is a worldwide used phenylpyrrol fungicide. This pesticide can induce serious effects on human health especially on nervous system. We assessed the role of oxidative stress in the toxicity of Fludioxonil and examined its apoptotic mechanism of action on rat neural cells (F98). We have shown that the increasing concentration of Fludioxonil reduces the percentage of living F98 cells viability and increases the levels of reactive oxygen species and malondialdheydes. The reduction of cells proliferation was demonstrated with an accumulation in G2/M phase. The immunocytochemical analysis has shown that Fludioxonil induced the disruption of the cytoskeleton. DNA damage was also provoked in a concentration dependent manner as illustrated by the comet assay. The depolarization of the mitochondria and the positive Annexin V FITC-PI confirmed the apoptosis induced by this fungicide. Interestingly, the F98 cells viability and ROS levels were restored with N-acetylcysteine pre-treatment. These results highlight the involvement of oxidative stress in the toxicity induced by this fungicide, and that free radicals generation plays a key role in the induction of apoptosis probably induced via the mitochondrial pathway.
Toxic effects of Fludioxonil on the growth, photosynthetic activity, oxidative stress, cell morphology, apoptosis, and metabolism of Chlorella vulgaris
Sci Total Environ 2022 Sep 10;838(Pt 2):156069.PMID:35605851DOI:10.1016/j.scitotenv.2022.156069.
Fludioxonil is widely used in the control of crop diseases because of its broad spectrum and high activity, but its presence is now common in waterways proximate to treated areas. This study examined the toxic effects and mechanisms of Fludioxonil on the microalgal taxa Chlorella vulgaris. The results showed that Fludioxonil limited the growth of C. vulgaris and the median inhibitory concentration at 96 h was 1.87 mg/L. Concentrations of 0.75 and 3 mg/L Fludioxonil reduced the content of photosynthetic pigments in algal cells to different degrees. Fludioxonil induced oxidative damage by altering C. vulgaris antioxidant enzyme activities and increasing reactive oxygen species levels. Fludioxonil at 0.75 mg/L significantly increased the activity of antioxidant enzymes. The highest level of activity was 1.60 times that of the control group. Both Fludioxonil treatment groups significantly increased ROS levels, with the highest increase being 1.90 times that of the control group. Transmission electron microscope showed that treatment with 3 mg/L Fludioxonil for 96 h disrupted cell integrity and changed cell morphology, and flow cytometer analysis showed that Fludioxonil induced apoptosis. Changes in endogenous substances indicated that Fludioxonil negatively affects C. vulgaris via altered energy metabolism, biosynthesis of amino acids, and unsaturated fatty acids. This study elucidates the effects of Fludioxonil on microalgae and the biological mechanisms of its toxicity, providing insights into the importance of the proper management of this fungicide.