| Size | Price | Stock | Qty |
|---|---|---|---|
| 5mg |
|
||
| 10mg |
|
||
| Other Sizes |
| Targets |
Pyrisoxazole targets the sterol 14alpha-demethylase (CYP51) enzyme in fungi. CYP51 is a cytochrome P450 enzyme that is essential for the biosynthesis of ergosterol, a critical component of the fungal cell membrane. By binding to the heme iron of the CYP51 enzyme, pyrisoxazole inhibits the demethylation of the C-14 position of sterol intermediates. This inhibition disrupts the synthesis of ergosterol, leading to the accumulation of toxic 14alpha-methylated sterols, which deform the cell membrane, impair its function, and ultimately cause fungal cell death. This mechanism is also known as the DMI (DeMethylation Inhibitor) mechanism, and pyrisoxazole is classified as a DMI fungicide.
|
|---|---|
| ln Vitro |
In vitro, pyrisoxazole shows potent activity against a broad range of plant pathogenic fungi. The minimum inhibitory concentration (MIC) values vary by species, but for Botrytis cinerea, the EC₅0 (half-maximal effective concentration) is typically in the range of 0.1-1 ug/mL. It has strong protective and curative activity when applied to plants prior to or after fungal infection. In mycelial growth inhibition assays, pyrisoxazole effectively prevents the growth of Fusarium graminearum, the causal agent of Fusarium head blight. It has also been shown to inhibit spore germination. In cross-resistance studies, it is effective against some strains that are resistant to other DMI fungicides, such as tebuconazole.
|
| ln Vivo |
In vivo, pyrisoxazole is used as a foliar spray to control diseases in field crops and greenhouses. In greenhouse trials on cucumber plants, an application of pyrisoxazole at 50-100 mg/L provides excellent control of powdery mildew, comparable to the commercial standard. In field trials for controlling tomato gray mold caused by Botrytis cinerea, pyrisoxazole shows strong protective and curative efficacy. It has systemic properties, being absorbed by the plant and translocated acropetally (moving upward) to protect new growth. Its in vivo efficacy has been demonstrated against a variety of diseases, including Fusarium head blight on wheat, where it reduces the level of mycotoxins (e.g., deoxynivalenol) in the grain. The compound also demonstrates rainfastness and a long duration of control.
|
| Enzyme Assay |
A typical non-cellular assay for pyrisoxazole is the CYP51 (sterol 14alpha-demethylase) enzyme inhibition assay. The enzyme is expressed in E. coli and purified. The assay mixture (200 uL) contains 0.1 M potassium phosphate buffer (pH 7.0), 10 mM glucose-6-phosphate, 1 U of glucose-6-phosphate dehydrogenase, 0.5 mM NADPH, 50 uM of the sterol substrate (e.g., 24-methylene-dihydrolanosterol), and 10-100 nM of the CYP51 enzyme. Pyrisoxazole is added at concentrations ranging from 0.001-10 uM. The reaction is initiated by the addition of NADPH. After incubation at 37degC for 20 minutes, the reaction is stopped, and the product (e.g., 14alpha-demethylated sterol) is extracted with organic solvent. The demethylated sterol is quantified by HPLC or GC-MS, and the IC₅0 is calculated.
|
| Cell Assay |
In vitro cell-based assays for pyrisoxazole are performed in a 96-well plate format using the target plant pathogenic fungus, such as Botrytis cinerea. The fungus is grown on potato dextrose agar (PDA) plates at 25degC for 7 days. Spores are harvested and adjusted to a concentration of 1 × 10⁵ spores/mL in potato dextrose broth (PDB). In a 96-well plate, 100 uL of the spore suspension is mixed with 100 uL of PDB containing varying concentrations of pyrisoxazole (0-100 ug/mL). The plate is incubated at 25degC for 48 hours. Mycelial growth is measured spectrophotometrically at 600 nm. The EC₅0 (concentration that inhibits 50% of fungal growth) is calculated using a logistic regression model. A control well with no fungicide is used as the growth control. The compound's ability to inhibit spore germination is also assessed microscopically after 12-24 hours of incubation.
|
| Animal Protocol |
An in vivo animal study is not typical for an agricultural fungicide like pyrisoxazole. Instead, its activity is assessed in greenhouse pot trials. For cucumber powdery mildew, cucumber plants (Cucumis sativus L.) are grown in pots until they reach the 2-3 true leaf stage. The plants are then inoculated with conidial spores of Sphaerotheca fuliginea (the causal agent) by dusting. One day after inoculation, the plants are sprayed to run-off with a solution of pyrisoxazole at 50, 100, and 200 mg/L. A control group is sprayed with water. Plants are kept in a greenhouse at 25degC. After 10 days, the disease severity is assessed on the leaves using a 0-9 scale based on the percentage of leaf area covered by the white powdery mycelia. The control efficacy is calculated. The compound's systemic activity is tested by applying it to the roots and assessing disease development on the leaves.
|
| ADME/Pharmacokinetics |
The pharmacokinetic (PK) properties of pyrisoxazole have been studied in plants. When applied to the leaf surface, pyrisoxazole is absorbed and translocated acropetally within the plant xylem, moving upwards to the leaves and stems. Its half-life in plants is typically 5-10 days, providing a medium duration of control. In the environment, it degrades through photolysis and microbial action. The compound is not typically evaluated for mammalian PK as a drug; however, a PK study in rats may be performed for pesticide registration. In such studies, it would likely have moderate oral absorption, be distributed to various tissues, and be metabolized by liver CYP450 enzymes. The metabolites and parent compound would be excreted primarily in feces and urine.
|
| Toxicity/Toxicokinetics |
The toxicity of pyrisoxazole is well-characterized as a pesticide. For mammals, it has low acute toxicity. The oral LD₅0 in rats is >5000 mg/kg, indicating a low risk of acute poisoning. It is not a skin or eye irritant. In subchronic studies, there may be effects on the liver at high doses, consistent with the mechanism of CYP51 inhibition, which can affect cholesterol synthesis in mammals. It is not classified as a mutagen or carcinogen. However, it is highly toxic to aquatic organisms, including fish and algae. Therefore, it is considered an environmental hazard. Standard pesticide safety handling guidelines must be followed when using this compound.
|
| References | |
| Additional Infomation |
3-[5-(4-chlorophenyl)-2,3-dimethyl-1,2-oxazolidine-3-yl]pyridine belongs to the oxazolidine class of compounds. It is formed by attaching a 3-pyridyl group and a 4-chlorophenyl group to the 3 and 5 positions of 2,3-dimethyl-1,2-oxazolidine, respectively. It belongs to the pyridine class, the oxazolidine class, and the monochlorobenzene class of compounds.
Pyrisoxazole is an agricultural fungicide and is not a drug for human use. It is approved for agricultural use in several countries (e.g., China) under the trade name SYP-Z048. Its mechanism of action is the inhibition of fungal sterol 14alpha-demethylase (CYP51), disrupting ergosterol synthesis and cell membrane integrity. It is used to control diseases in a variety of crops. This compound is for research use in agriculture and is not intended for human therapeutic applications. No clinical trials are associated with this compound. |
| Molecular Formula |
C16H17CLN2O
|
|---|---|
| Molecular Weight |
288.77198
|
| Exact Mass |
288.103
|
| CAS # |
847749-37-5
|
| PubChem CID |
11512926
|
| Appearance |
Typically exists as solid at room temperature
|
| LogP |
3.896
|
| Hydrogen Bond Donor Count |
0
|
| Hydrogen Bond Acceptor Count |
3
|
| Rotatable Bond Count |
2
|
| Heavy Atom Count |
20
|
| Complexity |
332
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
ClC1C=CC(C2ON(C)C(C3=CC=CN=C3)(C)C2)=CC=1
|
| InChi Key |
DHTJFQWHCVTNRY-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C16H17ClN2O/c1-16(13-4-3-9-18-11-13)10-15(20-19(16)2)12-5-7-14(17)8-6-12/h3-9,11,15H,10H2,1-2H3
|
| Chemical Name |
5-(4-chlorophenyl)-2,3-dimethyl-3-pyridin-3-yl-1,2-oxazolidine
|
| 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 | 3.4630 mL | 17.3148 mL | 34.6296 mL | |
| 5 mM | 0.6926 mL | 3.4630 mL | 6.9259 mL | |
| 10 mM | 0.3463 mL | 1.7315 mL | 3.4630 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
