yingweiwo

Pyrimethanil (Pyrimethanil)

Cat No.:V34777 Purity: ≥98%
Pyrimethanil is an aniline-pyrimidine broad-spectrum contact fungicide (fungicide) used to control Botrytis spp.
Pyrimethanil (Pyrimethanil)
Pyrimethanil (Pyrimethanil) Chemical Structure CAS No.: 53112-28-0
Product category: Fungal
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
50mg
Other Sizes

Other Forms of Pyrimethanil (Pyrimethanil):

  • Pyrimethanil-13C,15N2 (Pyrimethanil 13C,15N2)
  • Pyrimethanil-d5
Official Supplier of:
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Top Publications Citing lnvivochem Products
Product Description
Pyrimethanil is an aniline-pyrimidine broad-spectrum contact fungicide (fungicide) used to control Botrytis spp. on a variety of crops. Pyrimethanil inhibits the biosynthesis of methionine and other amino acid (AA)s in Botrytis cinerea. Pyrimethanil may be utilized in research related to the control of fungal diseases of fruits, vegetables and ornamental plants infected by mold.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
Pyrimethanil is a fungicide classified as anilinopyrimidines, specifically a strobilurin. After being exposed to two environmentally relevant concentrations of pyrimethanil for an extended period of time, the Italian tree frog H. intermedia's tissues may undergo histological changes and exhibit a variety of toxic reactions (5 and 50 µg/L)[2]. In the medium of three-day-old cultures, pyrimethanil reduces the activity of polygalacturonase, cellulase, proteinase, and laccase. For polygalacturonase, cellulase, and proteinase, the 50% reduction in total enzyme activity (IC50) caused by pyrimethanil is roughly 0.25 μM, and for laccase, it is approximately 1.0 μM[3].
ADME/Pharmacokinetics
Absorption, Distribution and Excretion
In rats, absorption, metabolism, and excretion are rapid. Following a single oral administration, over 95% is eliminated within 6–8 hours. Metabolism/Metabolites Metabolism involves oxidation to hydroxylated derivatives, followed by conjugation reactions. …Metabolism is minimal in fruits.
References
[1]. Petr Masner, et al. Possible methionine biosynthesis inhibition by pyrimidinamine fungicides. Pesticide Science
[2]. L Kanetis, et al. Characterization of genetic and biochemical mechanisms of fludioxonil and pyrimethanil resistance in field isolates of Penicillium digitatum. Phytopathology
[3]. Richard J. Milling, et al. Mode of action of the anilino‐pyrimidine fungicide pyrimethanil. 2. Effects on enzyme secretion in Botrytis cinerea. Volume45, Issue1, September 1995.
[4]. Salvatore D'Aquino, et al. Residue levels and effectiveness of pyrimethanil vs imazalil when using heated postharvest dip treatments for control of Penicillium decay on citrus fruit. J Agric Food Chem. 2006 Jun 28;54(13):4721-6.
Additional Infomation
Azoxystrobin belongs to the aminopyrimidine class of compounds, with the structure N-phenylpyrimidine-2-amine, and two methyl substituents at the 4 and 6 positions respectively. It is a fungicide used to control gray mold on fruits, vegetables, and ornamental plants, as well as leaf spot on pome fruits. In addition, it is commonly used to control gray mold in grapes, grape juice, fermented grape juice, and winemaking processes. Azoxystrobin possesses multiple properties, including being an aromatic hydrocarbon receptor agonist, an environmental pollutant, an exogenous substance, and an antifungal pesticide. It is an aminopyrimidine compound, belonging to the secondary amino compounds and phenylpyrimidine fungicides.
Azoxystrobin has been reported to exist in Ganoderma lucidum, and relevant data are available.
Azoxystrobin is a fungicide used on grapevines.
See also: Cyproterin (note moved to).
Mechanism of Action
/Its mode of action is/inhibiting the secretion of fungal pathogenic enzymes. This study investigated the effects of pyraclostrobin on the levels of cell wall-degrading enzymes secreted by Botrytis cinerea in diseased plant tissues and liquid cultures. Three days after inoculation, the total protease activity isolated from infected carrot slices treated with 5.0 μM pyraclostrobin decreased by 76%. After three days of culture in a medium containing pyraclostrobin, the activities of polygalacturonase, cellulase, protease, and laccase were all reduced. The pyraclostrobin concentration (IC50) that resulted in a 50% reduction in total enzyme activity was approximately 0.25 μM for polygalacturonase, cellulase, and protease, and approximately 1.0 μM for laccase. No significant growth inhibition was observed at these pyraclostrobin concentrations. Pyraclostrobin neither directly inhibits these enzymes nor inhibits cytoplasmic protein synthesis. Therefore, it is hypothesized that this fungicide inhibits protein secretion at the post-translational stage of the secretion pathway. The effects of pyraclostrobin on the growth of Botrytis cinerea on liquid media and agar plates differed significantly depending on the composition of the medium. In liquid media with cellulose and protein as carbon and nitrogen sources, 5.0 μM pyraclostrobin inhibited fungal growth; however, no growth inhibition was observed at 50 μM pyraclostrobin in malt extract. Similarly, on potato dextrose agar (PDA) medium, 0.5 μM pyraclostrobin promoted fungal growth, but no fungal growth was observed at this concentration on agar media containing cellulose and protein. Therefore, pyraclostrobin appears to have the highest activity in media where fungi must utilize extracellular enzymes to mobilize the nutrients required for their growth.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C12H13N3
Molecular Weight
199.25
Exact Mass
199.11
CAS #
53112-28-0
Related CAS #
Pyrimethanil-13C,15N2;Pyrimethanil-d5;2118244-83-8
PubChem CID
91650
Appearance
Colorless crystals
Density
1.1±0.1 g/cm3
Boiling Point
362.8±45.0 °C at 760 mmHg
Melting Point
96°C
Flash Point
173.2±28.7 °C
Vapour Pressure
0.0±0.8 mmHg at 25°C
Index of Refraction
1.622
LogP
2.84
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
2
Heavy Atom Count
15
Complexity
179
Defined Atom Stereocenter Count
0
SMILES
N([H])(C1C([H])=C([H])C([H])=C([H])C=1[H])C1=NC(C([H])([H])[H])=C([H])C(C([H])([H])[H])=N1
InChi Key
ZLIBICFPKPWGIZ-UHFFFAOYSA-N
InChi Code
InChI=1S/C12H13N3/c1-9-8-10(2)14-12(13-9)15-11-6-4-3-5-7-11/h3-8H,1-2H3,(H,13,14,15)
Chemical Name
4,6-dimethyl-N-phenylpyrimidin-2-amine
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

Note: This product requires protection from light (avoid light exposure) during transportation and storage.
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 : 130 mg/mL (652.45 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 3.25 mg/mL (16.31 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 32.5 mg/mL clear DMSO stock solution to 400 μL of PEG300 and mix evenly; then add 50 μL of Tween-80 to the above solution and mix evenly; then add 450 μL of 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: 3.25 mg/mL (16.31 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 32.5 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

View More

Solubility in Formulation 3: ≥ 3.25 mg/mL (16.31 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 32.5 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 5.0188 mL 25.0941 mL 50.1882 mL
5 mM 1.0038 mL 5.0188 mL 10.0376 mL
10 mM 0.5019 mL 2.5094 mL 5.0188 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.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
  • Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
  • Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume
An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
  • To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.
Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
/

Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
+
+
+

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.

Contact Us