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Penthiopyrad

Alias: Penthiopyrad; DPX-LEM 17; Gaia; MTF 753
Cat No.:V27269 Purity: ≥98%
Penthiopyrad (MTF-753) is a chiral carboxamide antifungal compound/agent with broad spectrum (a wide range) bactericidal ( bacteria killing) activity.
Penthiopyrad
Penthiopyrad Chemical Structure CAS No.: 183675-82-3
Product category: Fungal
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Penthiopyrad (MTF-753) is a chiral carboxamide antifungal compound/agent with broad spectrum (a wide range) bactericidal ( bacteria killing) activity. Penthiopyrad may be utilized to control foliar and soil-borne plant diseases of a variety of crops and lawns.
Penthiopyrad (CAS#: 183675-82-3) is a broad-spectrum pyrazole carboxamide fungicide belonging to the succinate dehydrogenase inhibitor (SDHI) class (FRAC Group 7). With a molecular formula of C16H20F3N3OS and a molecular weight of 359.41 g/mol, Penthiopyrad is a chiral fungicide. The compound's IUPAC name is 1-methyl-N-[2-(4-methylpentan-2-yl)thiophen-3-yl]-3-(trifluoromethyl)pyrazole-4-carboxamide. Penthiopyrad functions by inhibiting succinate dehydrogenase in the mitochondrial respiratory chain, which disrupts ATP production in fungi. It effectively controls a wide range of plant pathogens and can be used for controlling foliar and soil-borne plant diseases on a broad range of agricultural crops and turfgrass. Penthiopyrad is a fungicide and is not for human therapeutic use.
Biological Activity I Assay Protocols (From Reference)
Targets
Succinate dehydrogenase (complex II in the mitochondrial respiratory chain). Penthiopyrad is a succinate dehydrogenase inhibitor (SDHI). Succinate dehydrogenase is a critical enzyme in the mitochondrial respiratory chain that catalyzes the oxidation of succinate to fumarate. By inhibiting this enzyme, Penthiopyrad disrupts ATP production in fungi, leading to fungal growth inhibition and death. The compound is a broad-spectrum fungicide.
ln Vitro
Penthiopyrad demonstrates broad-spectrum fungicidal activity in vitro against a wide range of plant pathogens. Its activity is assessed by standard antifungal susceptibility testing methods. The compound's minimum inhibitory concentrations (MICs) against various fungal strains are well-characterized. Penthiopyrad is a broad-spectrum fungicide.
ln Vivo
Penthiopyrad is used in agriculture for controlling foliar and soil-borne plant diseases on a broad range of crops and turfgrass. The compound is effective against a wide range of plant pathogens. Its in vivo efficacy has been established through agricultural use. Penthiopyrad is a fungicide and is not for human therapeutic use.
Enzyme Assay
Antifungal susceptibility testing is performed using broth microdilution or agar dilution methods according to CLSI guidelines. Fungal strains are cultured in appropriate media. Penthiopyrad is serially diluted and tested against the fungi. MIC values are determined as the lowest concentration causing complete inhibition of visible growth. Quality control strains are included to ensure assay validity.
Cell Assay
Antifungal activity is evaluated in fungal cultures using standard microbiological methods. Broth microdilution assays are performed in 96-well plates with appropriate media. Fungi are cultured to logarithmic phase and diluted to a standard inoculum. Penthiopyrad is serially diluted and added to wells. Plates are incubated at appropriate temperatures for 24-48 hours. MIC values are determined visually or using a microplate reader. Each experiment includes quality control strains and fungicide standards.
Animal Protocol
In vivo efficacy is evaluated in plant models of fungal disease. Penthiopyrad is applied as a foliar spray or soil drench at recommended application rates. Disease severity is assessed by visual inspection and measurement of lesion size. Crop yield and quality are assessed.
ADME/Pharmacokinetics
Molecular Weight: 359.41. Formula: C16H20F3N3OS. CAS No.: 183675-82-3. IUPAC Name: 1-methyl-N-[2-(4-methylpentan-2-yl)thiophen-3-yl]-3-(trifluoromethyl)pyrazole-4-carboxamide. Synonyms: MTF-753, Vertisan, DPX-LEM 17, Gaia. Purity: ≥98%. Appearance: Solid. Solubility: Organic solvents. Storage: Typically at room temperature. Penthiopyrad is a broad-spectrum SDHI fungicide.
Toxicity/Toxicokinetics
Penthiopyrad has been evaluated for toxicity as a fungicide. It is a fungicide and is not intended for human consumption. Regulatory approvals exist for agricultural use. Safety data sheets provide detailed handling and safety information.
References

[1].Haptens, bioconjugates, and antibodies for penthiopyrad immunosensing. Analyst. 2014 Nov 7;139(21):5358-61.

[2].Effects of penthiopyrad on the development and behaviour of zebrafish in early-life stages. Chemosphere. 2019 Jan;214:184-194

Additional Infomation
1-Methyl-N-[2-(4-methylpent-2-yl)-3-thienyl]-3-(trifluoromethyl)pyrazole-4-carboxamide is an aromatic amide formed by the condensation of the carboxyl group of 1-methyl-3-(trifluoromethyl)pyrazole-4-carboxylic acid with the amino group of 2-(4-methylpent-2-yl)thien-3-amine. It is an aromatic amide, an organofluorine compound, and belongs to the pyrazole and thiophene classes of compounds.
Penthiopyrad is also known as MTF-753, Vertisan, DPX-LEM 17, and Gaia. Its IUPAC name is 1-methyl-N-[2-(4-methylpentan-2-yl)thiophen-3-yl]-3-(trifluoromethyl)pyrazole-4-carboxamide. Penthiopyrad is a broad-spectrum pyrazole carboxamide fungicide belonging to the SDHI class. It inhibits succinate dehydrogenase in the mitochondrial respiratory chain. It is used to control foliar and soil-borne plant diseases. Regulatory approvals exist for agricultural use.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C16H20F3N3OS
Molecular Weight
359.4112
Exact Mass
359.127
Elemental Analysis
C, 53.47; H, 5.61; F, 15.86; N, 11.69; O, 4.45; S, 8.92
CAS #
183675-82-3
PubChem CID
11388558
Appearance
Solid powder
Density
1.3±0.1 g/cm3
Boiling Point
381.3±42.0 °C at 760 mmHg
Melting Point
103-105ºC
Flash Point
184.4±27.9 °C
Vapour Pressure
0.0±0.9 mmHg at 25°C
Index of Refraction
1.561
LogP
3.86
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
6
Rotatable Bond Count
5
Heavy Atom Count
24
Complexity
447
Defined Atom Stereocenter Count
0
SMILES
O=C(C1=CN(C)N=C1C(F)(F)F)NC2=C(C(C)CC(C)C)SC=C2
InChi Key
PFFIDZXUXFLSSR-UHFFFAOYSA-N
InChi Code
InChI=1S/C16H20F3N3OS/c1-9(2)7-10(3)13-12(5-6-24-13)20-15(23)11-8-22(4)21-14(11)16(17,18)19/h5-6,8-10H,7H2,1-4H3,(H,20,23)
Chemical Name
1-Methyl-N-[2-(4-methylpentan-2-yl)thiophen-3-yl]-3-(trifluoromethyl)pyrazole-4-carboxamide
Synonyms
Penthiopyrad; DPX-LEM 17; Gaia; MTF 753
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 Data
Solubility (In Vitro)
DMSO : ~100 mg/mL (~278.23 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (5.79 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.08 mg/mL (5.79 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.7823 mL 13.9117 mL 27.8234 mL
5 mM 0.5565 mL 2.7823 mL 5.5647 mL
10 mM 0.2782 mL 1.3912 mL 2.7823 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.

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Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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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.
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