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Meptyldinocap (also known as 2,4-DNOPC) is a novel and potent powdery mildew (Erysiphe necator) fungicide which shows protectant and post-infective activities.
| ln Vivo |
The study investigated the dissipation behavior and final residue levels of meptyldinocap in cucumber plants and soil under field conditions in China.
The initial deposit concentrations of meptyldinocap on cucumbers 2 hours after application at 315 g a.i. ha⁻¹ ranged from 0.55 to 0.83 mg kg⁻¹ across three trial sites. The residue levels declined rapidly following first-order kinetics. In cucumbers, over 75% of the initial residue dissipated within 3 days, and over 95% within 7 days post-application across all sites. Similarly, in soil, over 75% dissipation occurred within 5 days, and over 95% within 21 days post-application.[1] |
|---|---|
| Animal Protocol |
Field Dissipation and Terminal Residue Trials: The study was conducted in cucumber fields at three locations in China (Nanjing, Nanning, Beijing).
Experimental plots (30 m² each) included treatments for dissipation dynamics (single application at 315 g a.i. ha⁻¹) and final residue studies (3 or 4 applications at 210 or 315 g a.i. ha⁻¹, with 7-day intervals). A commercial formulation of meptyldinocap (35% EC) was sprayed using a backpack sprayer. For the dissipation study, cucumber and soil (0-10 cm depth) samples were collected at 0 (2 h), 1, 2, 3, 5, 7, 10, 14, and 21 days after the single application. For the final residue study, samples were collected at 1, 3, 5, and 7 days after the last application. Cucumber samples (whole fruit without stems) were chopped and homogenized. All samples were stored at -18°C until analysis.[1] |
| ADME/Pharmacokinetics |
Degradation kinetics and half-life: Under field conditions, the degradation of meperone in cucumber and soil followed first-order kinetics. The half-lives (t₁/₂) of meperone in cucumber at the three test sites were 1.6, 1.6 and 2.2 days, respectively. The half-lives of meperone in soil at the three test sites were 3.1, 3.6 and 4.4 days, respectively. The degradation rate in cucumber substrate was faster than that in soil. [1] Final residues: At the recommended dose (210 g ai ha⁻¹, applied 3 times), the residues of meperone in cucumber were 0.01 to 0.08 mg 5 days after the last application (pre-harvest interval, PHI=5). The residues in soil were below the EU maximum residue limit (MRL) of 0.1 mg kg⁻¹ at all test sites.
At higher doses (315 g ai ha⁻¹, 4 applications), the residue levels in cucumbers 5 days before harvest were 0.03 to 0.08 mg kg⁻¹. During the corresponding time intervals, the residue levels in the soil were generally lower than those in the cucumbers. [1] |
| References | |
| Additional Infomation |
Dinitrophenol may cause developmental toxicity depending on state or federal labeling requirements. 2,4-Dinitro-6-(oct-2-yl)phenyl(E)-but-2-enoate is an enoate formed by the condensation of the carboxyl group of 3-methacrylic acid with the phenolic hydroxyl group of 2,4-dinitro-6-(oct-2-yl)phenol. It is a C-nitro compound and also an enoate. Methoxydinitrophenol (2,4-DNOPC) is a monomeric fungicide (the methyl-heptyl isomer of dinitrophenol) used to control powdery mildew (Erysiphe necator), exhibiting protective and post-infection activity. This product is designed to replace the older mixed product, dinitrobenzoate, and provides superior toxicological properties. [1]
The EU has set the maximum residue limit (MRL) for methyl dinitrobenzoate (the sum of 2,4-dinitrobenzoate and its metabolite 2,4-dinitrobenzoate) in cucumber at 0.1 mg kg⁻¹. Based on data on declining residue levels, this study recommends a 5-day interval before harvest when applying at the recommended dose and frequency to ensure that the residue level in cucumber is below the MRL. [1] Analytical method: This study developed and validated a liquid chromatography-tandem mass spectrometry (LC-MS/MS) method for determining trace amounts of methyl dinitrobenzoate in cucumber and soil. Due to its instability, the parent compound (2,4-dinitrooctylphenol, 2,4-DNOPC) was derivatized to the stable metabolite 2,4-dinitrooctylphenol (2,4-DNOP) before analysis. The average recoveries of this method in spiked samples were 81.4%–95.1%, and the limits of quantitation (LOQ) for both matrices were 0.01 mg kg⁻¹. [1] |
| Molecular Formula |
C18H24N2O6
|
|---|---|
| Molecular Weight |
364.4
|
| Exact Mass |
364.163
|
| CAS # |
131-72-6
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| PubChem CID |
5284389
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| Appearance |
Typically exists as solid at room temperature
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| Density |
1.175 g/cm3
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| Boiling Point |
473.7ºC at 760 mmHg
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| Flash Point |
173.9ºC
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| Vapour Pressure |
3.85E-09mmHg at 25°C
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| Index of Refraction |
1.54
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| LogP |
6.104
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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 |
9
|
| Heavy Atom Count |
26
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| Complexity |
511
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C/C=C/C(OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1C(C)CCCCCC)=O
|
| InChi Key |
NIOPZPCMRQGZCE-WEVVVXLNSA-N
|
| InChi Code |
InChI=1S/C18H24N2O6/c1-4-6-7-8-10-13(3)15-11-14(19(22)23)12-16(20(24)25)18(15)26-17(21)9-5-2/h5,9,11-13H,4,6-8,10H2,1-3H3/b9-5+
|
| Chemical Name |
(2,4-dinitro-6-octan-2-ylphenyl) (E)-but-2-enoate
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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 : ≥ 150 mg/mL (~411.65 mM)
Ethanol : ~100 mg/mL (~274.43 mM) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (6.86 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 (6.86 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 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. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.7442 mL | 13.7212 mL | 27.4424 mL | |
| 5 mM | 0.5488 mL | 2.7442 mL | 5.4885 mL | |
| 10 mM | 0.2744 mL | 1.3721 mL | 2.7442 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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