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| Other Sizes |
| Targets |
Isoprothiolane targets phospholipid N-methyltransferase, an enzyme involved in fungal membrane biosynthesis. After absorption by rice plants, the compound inhibits pathogen invasion by specifically inhibiting phospholipid N-methyltransferase, thereby suppressing pathogen growth and providing both preventive and therapeutic effects. The compound also has the effect of suppressing planthopper and white-backed planthopper populations. As a systemic fungicide, Isoprothiolane is absorbed and distributed throughout the plant, providing comprehensive protection against fungal pathogens.
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| ln Vitro |
Isoprothiolane demonstrates in vitro antifungal activity against rice blast fungus (Pyricularia oryzae), Fusarium wilt, and Fusarium nivale. The compound's mechanism of action involves inhibition of phospholipid N-methyltransferase, which disrupts fungal membrane biosynthesis and inhibits pathogen growth. The compound's efficacy against multiple fungal pathogens makes it a valuable tool for agricultural disease management. Detailed MIC values and spectrum of activity are available in the agricultural research literature.
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| ln Vivo |
Isoprothiolane demonstrates in vivo efficacy as a systemic fungicide in rice plants. After absorption by rice plants, the compound inhibits pathogen invasion and provides both preventive and therapeutic effects against rice blast disease. The compound also suppresses planthopper and white-backed planthopper populations. Its systemic properties allow it to protect the entire plant from fungal infection. Field studies have demonstrated its effectiveness in controlling rice blast disease under various environmental conditions.
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| Enzyme Assay |
For antifungal activity testing, fungal cultures (Pyricularia oryzae, Fusarium species) are grown on appropriate agar media and treated with Isoprothiolane at various concentrations. Minimum inhibitory concentration (MIC) is determined by broth microdilution following standard agricultural fungicide testing protocols. For enzyme inhibition assays, phospholipid N-methyltransferase is extracted from fungal cells and incubated with the compound and radiolabeled S-adenosylmethionine, and methyltransferase activity is measured by incorporation of methyl groups into phospholipids.
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| Cell Assay |
For antifungal activity evaluation, fungal cultures are grown in appropriate liquid media at 25-28°C. Fungal spores or mycelial fragments are seeded in 96-well plates and treated with Isoprothiolane at various concentrations (typically 0.1-100 μg/mL). Plates are incubated for 48-72 hours, and fungal growth is assessed by measuring optical density at 600 nm or by colony counting on agar plates. MIC is determined as the lowest concentration that inhibits visible fungal growth. For agricultural applications, the compound is tested on plants grown in greenhouse conditions.
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| Animal Protocol |
For in vivo efficacy studies in plants, rice plants are grown in greenhouse conditions and inoculated with Pyricularia oryzae spores. Isoprothiolane is applied as a foliar spray or soil drench at various concentrations. Disease severity is assessed by visual scoring of lesion development on leaves and panicles. For planthopper control, plants are infested with planthoppers and the compound is applied, with insect mortality and population reduction assessed over time. Efficacy is compared to untreated controls and standard fungicides.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of Isoprothiolane in plants have been characterized. As a systemic fungicide, it is absorbed by rice plants and distributed throughout the plant tissues. The compound is readily soluble in benzene, alcohol, acetone, and other organic solvents. It has low toxicity and low residue properties. The compound's metabolism and persistence in plants and the environment have been studied as part of its agricultural registration. Detailed PK parameters in animals are available in the toxicological literature.
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| Toxicity/Toxicokinetics |
Isoprothiolane is classified as an efficient, low-toxicity, and low-residue organosulfur fungicide. It is used to control rice blast disease and has the additional effect of suppressing planthopper and white-backed planthopper populations. The compound is generally considered safe for agricultural use when applied according to label instructions. Toxicological studies have been conducted as part of its regulatory approval for agricultural use. Standard safety precautions for pesticide handling should be followed.
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| References |
[1]. Matazaemon Uchida, et al. Effect of a Rice Blast Controlling Agent, Isoprothiolane, on Nilaparvata Lugens Stal with Different Levels of Susceptibility to Diazinon. Pest Resistance to Pesticides pp 421-428
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| Additional Infomation |
Isoprothiolane is a malonate, specifically a diisopropylmalonate, in which the two methylene hydrogens at the 2-position are replaced by 1,3-dithiocyclopentane-2-alkylene groups. It is an insecticide and fungicide used to control a variety of diseases, including rice blast fungus, Fusarium wilt, and Fusarium nivale. It possesses multiple functions, including insecticidal, environmentally friendly, phospholipid biosynthesis inhibitor, and antifungal pesticide application. It is a malonate, belonging to the dithiocyclopentane class of compounds, and is also an isopropyl ester. Functionally, it is related to malonic acid. It is derived from the hydride of 1,3-dithiocyclopentane.
Isoprothiolane is a dithiolane pesticide used as a fungicide to control rice blast disease and other fungal pathogens, with molecular formula C12H18O4S2 and molecular weight 290.40. It targets phospholipid N-methyltransferase in fungal cells. The compound is systemic in plants, providing preventive and therapeutic effects. It is classified as low-toxicity and low-residue. Isoprothiolane is approved for agricultural use in rice cultivation. Standard safety precautions for pesticide handling should be followed. |
| Molecular Formula |
C12H18O4S2
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|---|---|
| Molecular Weight |
290.40
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| Exact Mass |
290.065
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| CAS # |
50512-35-1
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| Related CAS # |
Isoprothiolane-d4;1715020-82-8
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| PubChem CID |
39681
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| Appearance |
Light yellow to yellow solid powder
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| Density |
1.228 g/cm3
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| Boiling Point |
353ºC at 760 mmHg
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| Melting Point |
50 - 54.5 °C
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| Flash Point |
159ºC
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| Index of Refraction |
1.546
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| LogP |
2.581
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
6
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| Heavy Atom Count |
18
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| Complexity |
329
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CC(C)OC(=O)C(=C1SCCS1)C(=O)OC(C)C
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| InChi Key |
UFHLMYOGRXOCSL-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C12H18O4S2/c1-7(2)15-10(13)9(11(14)16-8(3)4)12-17-5-6-18-12/h7-8H,5-6H2,1-4H3
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| Chemical Name |
dipropan-2-yl 2-(1,3-dithiolan-2-ylidene)propanedioate
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| HS Tariff Code |
2934.99.9001
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| 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)
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| Solubility (In Vitro) |
DMSO : 100 mg/mL (344.35 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (8.61 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 25.0 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: ≥ 2.5 mg/mL (8.61 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in 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 25.0 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: ≥ 2.5 mg/mL (8.61 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.4435 mL | 17.2176 mL | 34.4353 mL | |
| 5 mM | 0.6887 mL | 3.4435 mL | 6.8871 mL | |
| 10 mM | 0.3444 mL | 1.7218 mL | 3.4435 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.
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