| Size | Price | Stock | Qty |
|---|---|---|---|
| 10mg |
|
||
| 25mg |
|
||
| 50mg |
|
||
| Other Sizes |
| Targets |
Succinate dehydrogenase (SDH; complex II of the mitochondrial electron transport chain). Penflufen is a succinate dehydrogenase inhibitor (SDHI). It binds to the ubiquinone-binding site of succinate dehydrogenase (also known as mitochondrial complex II), inhibiting the conversion of succinate to fumarate and the reduction of ubiquinone to ubiquinol. This blocks the tricarboxylic acid (TCA) cycle and the electron transport chain, leading to decreased ATP production and accumulation of reactive oxygen species (ROS), ultimately causing fungal cell death. Penflufen is a highly efficient, broad-spectrum succinate dehydrogenase inhibitor (SDHI).
|
|---|---|
| ln Vitro |
Penflufen exhibits broad-spectrum in vitro antifungal activity against a variety of plant pathogenic fungi, including Rhizoctonia solani (causes potato black scurf, rice sheath blight), Rhizoctonia cerealis (wheat sharp eyespot), Fusarium species, Sclerotinia sclerotiorum, and Botrytis cinerea. The effective concentration (EC50) values vary by fungal species but are typically in the range of 0.01-1 ug/mL. Penflufen is a highly efficient, broad-spectrum succinate dehydrogenase inhibitor (SDHI). It can be used as a fungicide and has broad bioactivity against many fungal diseases.
|
| ln Vivo |
Penflufen is an agricultural fungicide that is effective in controlling fungal diseases in various crops. In field trials, Penflufen has demonstrated efficacy in controlling potato black scurf (caused by Rhizoctonia solani) when applied as a seed treatment, wheat sharp eyespot (R. cerealis), rice sheath blight (R. solani), and root rot in peanuts and other crops. It is used as a fungicide and has broad bioactivity against many fungal diseases.
|
| Enzyme Assay |
A typical cell-free assay for succinate dehydrogenase (SDH) inhibition is as follows. Succinate dehydrogenase (complex II) is extracted from fungal mitochondria (e.g., from R. solani or R. cerealis). Mitochondria are isolated by differential centrifugation and lysed. The enzyme preparation (2-10 ug protein) is incubated with various concentrations of Penflufen (0.001-100 uM) in assay buffer (50 mM potassium phosphate buffer, pH 7.4, 5 mM MgCl2, 1 mM EDTA) at 30degC for 5-10 minutes. The reaction is started by adding succinate (20 mM) and 2,6-dichlorophenolindophenol (DCPIP, 0.1 mM) as an electron acceptor. The reduction of DCPIP (decrease in blue color) is measured spectrophotometrically at 600 nm over 5-10 minutes. Alternatively, coenzyme Q1 (ubiquinone-1) can be used as the electron acceptor, and the reduction of coenzyme Q1 is measured by HPLC. The IC50 value is determined by plotting percent inhibition against inhibitor concentration. Penflufen is a succinate dehydrogenase inhibitor. Penflufen is a highly efficient, broad-spectrum succinate dehydrogenase inhibitor (SDHI).
|
| Cell Assay |
For in vitro antifungal assays, plant pathogenic fungi (e.g., Rhizoctonia solani, R. cerealis, Fusarium graminearum) are cultured on potato dextrose agar (PDA) at 25degC for 3-7 days. Mycelial plugs (5 mm diameter) are cut from the edge of actively growing colonies and transferred to PDA plates amended with various concentrations of Penflufen (0.001-100 ug/mL). Plates are incubated at 25degC for 2-5 days. Mycelial growth diameter is measured, and the percent inhibition of radial growth is calculated relative to the untreated control. The EC50 (effective concentration for 50% inhibition of mycelial growth) is determined by nonlinear regression. For spore germination assays, spores are harvested and suspended in sterile water. Penflufen is added at various concentrations, and after incubation at 25degC for 12-24 hours, the percent germination is determined microscopically. Penflufen is a highly efficient, broad-spectrum succinate dehydrogenase inhibitor (SDHI). Penflufen can be used as a fungicide and has broad bioactivity against many fungal diseases.
|
| Animal Protocol |
No specific in vivo animal study protocols are documented, as Penflufen is an agricultural fungicide, not a pharmaceutical. Efficacy trials are conducted in greenhouse or field settings. For a potato black scurf (R. solani) efficacy trial, potato seed tubers are treated with Penflufen as a seed tuber dip or as a dust formulation at various concentrations (e.g., 0.5-5 g active ingredient/100 kg seed). The seed tubers are planted in Rhizoctonia-infested soil. Control groups include untreated seed and a positive control fungicide (e.g., fludioxonil). At harvest (90-120 days after planting), tubers are evaluated for black scurf disease severity (percentage of tuber surface covered with sclerotia). For wheat sharp eyespot (R. cerealis), seeds are treated with Penflufen (e.g., 10-50 g a.i./100 kg seed) and planted in infested soil. At various time points post-planting, plants are assessed for disease severity (lesion length on stems), and yield parameters are measured at harvest. Penflufen can be used as a fungicide and has broad bioactivity against many fungal diseases, including potato black scurf, wheat sharp eyespot, rice sheath blight, and root rot in peanut and other similar fungal diseases.
|
| ADME/Pharmacokinetics |
No pharmacokinetic data has been reported for Penflufen in animals, as it is an agricultural fungicide. In plants, Penflufen is absorbed by seeds and roots and translocated acropetally (upward) in the xylem. It has systemic activity. The half-life in soil is variable (weeks to months). In mammals, Penflufen is metabolized by liver CYP enzymes and excreted in urine and feces. The acute oral LD50 in rats is >2000 mg/kg, indicating low acute toxicity.
|
| Toxicity/Toxicokinetics |
Penflufen has low acute toxicity to mammals. The acute oral LD50 in rats is >2000 mg/kg. The acute dermal LD50 is >2000 mg/kg. It is not a skin sensitizer. It may be slightly toxic to aquatic organisms (fish, algae, daphnia). It is not genotoxic or carcinogenic in standard assays. It is for agricultural use and should be handled with appropriate personal protective equipment (gloves, goggles, protective clothing). It is not approved for human or veterinary pharmaceutical use.
|
| References |
[1]. Fang K, et al. Systematic evaluation of chiral fungicide penflufen for the bioactivity improvement and input reduction using alphafold2 models and transcriptome sequencing. J Hazard Mater. 2022 Oct 15;440:129729.
|
| Additional Infomation |
5-Fluoro-1,3-dimethyl-N-[2-(4-methylpent-2-yl)phenyl]pyrazole-4-carboxamide is an aromatic amide formed by the condensation of the carboxyl group of 5-fluoro-1,3-dimethylpyrazole-4-carboxylic acid with the amino group of 2-(4-methylpent-2-yl)aniline. It is an aromatic amide, an organofluorine compound, and a member of the pyrazole class of compounds.
Penflufen is a pyrazole carboxamide fungicide belonging to the succinate dehydrogenase inhibitor (SDHI) class. The molecular formula is C18H24FN3O, and the molecular weight is 317.40. The IUPAC name is 5-fluoro-1,3-dimethyl-N-[2-(4-methylpentan-2-yl)phenyl]pyrazole-4-carboxamide. It is a racemic mixture of R and S enantiomers. It is used in agriculture to control soil-borne and foliar fungal diseases. It is not approved for human or veterinary use. It is available as a research chemical for agrochemical and antifungal research. |
| Molecular Formula |
C18H24FN3O
|
|---|---|
| Molecular Weight |
317.40
|
| Exact Mass |
317.19
|
| CAS # |
494793-67-8
|
| PubChem CID |
11674113
|
| Appearance |
White to off-white solid powder
|
| Density |
1.128g/cm3
|
| Boiling Point |
381.002ºC at 760 mmHg
|
| Flash Point |
184.224ºC
|
| Index of Refraction |
1.555
|
| LogP |
4.653
|
| Hydrogen Bond Donor Count |
1
|
| Hydrogen Bond Acceptor Count |
3
|
| Rotatable Bond Count |
5
|
| Heavy Atom Count |
23
|
| Complexity |
404
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
CC1=NN(C(=C1C(=O)NC2=CC=CC=C2C(C)CC(C)C)F)C
|
| InChi Key |
GOFJDXZZHFNFLV-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C18H24FN3O/c1-11(2)10-12(3)14-8-6-7-9-15(14)20-18(23)16-13(4)21-22(5)17(16)19/h6-9,11-12H,10H2,1-5H3,(H,20,23)
|
| Chemical Name |
5-fluoro-1,3-dimethyl-N-[2-(4-methylpentan-2-yl)phenyl]pyrazole-4-carboxamide
|
| HS Tariff Code |
2934.99.9001
|
| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
|
|---|---|
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.1506 mL | 15.7530 mL | 31.5060 mL | |
| 5 mM | 0.6301 mL | 3.1506 mL | 6.3012 mL | |
| 10 mM | 0.3151 mL | 1.5753 mL | 3.1506 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
