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| Targets |
Metolachlor-d6 is a labeled analog of Metolachlor, which is a chiral herbicide composed of four stereoisomers. The primary mechanism of action of Metolachlor involves the inhibition of very-long-chain fatty acid (VLCFA) synthesis. By targeting elongase enzymes, particularly those in the endoplasmic reticulum, Metolachlor disrupts the formation of the C20 and C22 fatty acids that are essential for cell membrane integrity and function. This inhibition interferes with cell division, particularly in the shoots of developing seedlings, leading to suppressed growth and eventual death of susceptible weed species. The herbicide has minimal effects on root development. The deuterated version, Metolachlor-d6, mimics this activity but is not used for herbicidal application; instead, it is utilized as an internal standard to accurately track and quantify the parent compound in biological and environmental samples.
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| ln Vitro |
Drug compounds have included stable heavy isotopes of carbon, hydrogen, and other elements, mostly as quantitative tracers while the drugs were being developed. Because deuteration may have an effect on a drug's pharmacokinetics and metabolic properties, it is a cause for concern [1].
The in vitro activity of Metolachlor-d6 is inferred from its non-labeled parent compound, Metolachlor. In vitro studies have demonstrated that Metolachlor inhibits cell division and growth of suspension cultures of maize (Zea mays) and other plant species with IC₅0 values in the micromolar range. At the cellular level, the herbicide disrupts the synthesis of very-long-chain fatty acids (C20 and C22), as measured in assays using isolated plant microsomes. This disrupts the elongation of fatty acids, leading to abnormal cell expansion and inhibition of shoot emergence. The labeled Metolachlor-d6 itself is rarely used directly in bioassays; it is instead spiked into samples as an internal standard for LC-MS analysis to accurately quantify Metolachlor concentrations in in vitro treatments, ensuring reliability in studies assessing its phytotoxic effects and metabolic pathways. |
| ln Vivo |
Metolachlor-d6 is the labeled form of Metolachlor, a pre-emergent herbicide that exhibits in vivo activity by inhibiting the growth of monocotyledonous and dicotyledonous weeds. After soil application, the herbicide is absorbed primarily by the shoots and coleoptiles of emerging seedlings. Systemically translocated within the plant, it acts by inhibiting the synthesis of very-long-chain fatty acids, which are crucial for cell division and expansion in growing tissues. Field studies show effective control of annual grasses such as foxtail and crabgrass, as well as broadleaf weeds like pigweed, when applied at pre-emergence rates of 1.0-2.5 kg/ha. Metolachlor-d6 serves as an internal standard for the precise quantification of the herbicide and its metabolites in environmental samples, enabling accurate risk assessment studies related to its herbicidal efficacy and persistence.
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| Enzyme Assay |
A generic non-cell-based assay protocol for Metolachlor-d6 involves an enzyme inhibition study targeting very-long-chain fatty acid elongase. Isolate microsomes from etiolated maize seedlings or commercially sourced plant tissue. Prepare a reaction mixture containing 100 mM HEPES (pH 7.5), 10 mM MgCl2, 10 mM ATP, 5 uM CoA, 5 mM malonyl-CoA, 2 uM [14C]-labeled fatty acid substrate (e.g., C20:0-CoA). Add varying concentrations of unlabeled Metolachlor (1 nM to 100 uM) to the reaction mixture. Pre-incubate the mixture for 5 minutes at 30degC. Initiate the reaction by adding 50 ug of microsomal protein. Incubate for 30 minutes. Terminate the reaction by adding 0.5 mL of 1 M KOH in methanol. After saponification, extract the fatty acid products into hexane and analyze by scintillation counting. Calculate the half-maximal inhibitory concentration (IC₅0) from the dose-response curve. Metolachlor-d6 is used as an LC-MS internal standard to validate the concentrations of Metolachlor in the incubation medium.
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| Cell Assay |
Metolachlor-d6 is a stable isotope-labeled compound, and a standard in vitro cell-based assay for its parent compound involves plant cell suspension cultures. A typical protocol uses maize (Zea mays) Black Mexican Sweet (BMS) cells. Grow the cell cultures in Murashige and Skoog (MS) medium supplemented with 3% sucrose and 2,4-dichlorophenoxyacetic acid (2,4-D) at 25degC in the dark on a rotary shaker. Subculture weekly. For the assay, transfer 2-3 mL of settled cell volume to fresh medium in 25 mL of total volume. Treat the cultures with increasing concentrations of unlabeled Metolachlor (0.1 to 500 uM). Incubate for 3-7 days. Harvest cells by vacuum filtration, determine fresh weight, and lyophilize to measure dry weight. Assess cell viability using the Evans blue staining method or a fluorescein diacetate assay. Use Metolachlor-d6 as an internal standard to quantify the parent compound in both the culture medium and the harvested cells using LC-MS analysis. The EC₅0 (effective concentration causing 50% growth inhibition) can then be calculated.
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| Animal Protocol |
A standard in vivo experiment for Metolachlor-d6 and its parent compound involves a greenhouse-based weed control efficacy study. For this protocol, prepare soil-filled pots (10 cm diameter) and plant seeds of a target weed species (e.g., Echinochloa crus-galli) at a depth of 0.5-1 cm. Maintain the soil at 70-80% field capacity. On the same day of planting, prepare a commercial formulation of unlabeled Metolachlor (e.g., Dual Magnum) in water at application rates equivalent to 1.0-2.5 kg a.i./ha (active ingredient per hectare). Apply the treatment uniformly to the soil surface using a laboratory track sprayer calibrated to deliver 200 L/ha. Maintain the pots in a greenhouse under natural light with temperatures of 25/20degC (day/night). Assess weed control visually or by shoot biomass harvest at 14-28 days after treatment (DAT). For residue analysis, collect soil core samples at various depths and plant tissue, extract with organic solvent (e.g., acetonitrile), and analyze using LC-MS/MS with Metolachlor-d6 as the internal standard to accurately quantify the concentration of residues and assess dissipation.
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| ADME/Pharmacokinetics |
Metolachlor-d6 is a deuterium-labeled compound that is not intended for pharmacokinetic studies in animals; however, the PK of its non-labeled parent is well-characterized. Metolachlor is rapidly absorbed following oral administration in rats, with peak plasma concentrations observed within 1-2 hours. It is extensively distributed, with tissue residues highest in the liver, kidneys, and fat. The metabolism of Metolachlor is extensive, primarily occurring via conjugation with glutathione, which is a common pathway for chloroacetanilide herbicides. Excretion occurs predominantly in urine (approx. 40-60%) and feces (approx. 30-50%) within 72 hours post-dosing. The parent compound is detected in the environment with a half-life ranging from 15 to 25 days in soil depending on microbial activity and organic matter content. Metolachlor-d6 is used as an internal standard to accurately quantify the parent herbicide and its metabolites in PK studies.
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| Toxicity/Toxicokinetics |
The toxicity of Metolachlor-d6 itself has not been fully characterized, but it is generally considered to be safe for handling at low concentrations for analytical purposes, referring to its unlabeled analog. Metolachlor is classified by the EPA as a Group C possible human carcinogen based on an increased incidence of liver tumors in female rats. Acute oral LD₅0 values for Metolachlor are >2000 mg/kg in rats, indicating low acute toxicity. It is a slight skin and eye irritant but not a skin sensitizer. Subchronic exposure has been associated with increased liver weight and hepatocyte hypertrophy in animal studies. In the environment, Metolachlor is moderately toxic to fish (96-h LC₅0 of 2-15 mg/L for rainbow trout) and practically non-toxic to honeybees (LD₅0 > 200 ug/bee). Standard safety precautions including gloves and goggles should be used while handling the labeled compound.
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| References |
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| Additional Infomation |
Metolachlor-d6 is exclusively intended for research applications, particularly as a stable isotope-labeled internal standard for quantitative analysis using mass spectrometry (LC-MS/MS). It enables the precise determination of Metolachlor and its primary metabolites in various matrices including water, soil, crops, and biological specimens. Its primary application lies in environmental monitoring, residue analysis in food products, and metabolic studies to understand herbicide fate. Metolachlor itself is a widely used herbicide for controlling annual grasses and broadleaf weeds in corn, soybeans, and other major crops. As a chiral herbicide, it comprises four stereoisomers, each with varying biological activities and degradation rates. The labeled analog supports studies on the environmental impact, efficacy, and regulatory compliance of this important agrochemical.
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| Molecular Formula |
C15H16D6CLNO2
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| Molecular Weight |
289.83
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| Exact Mass |
289.171
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| CAS # |
1219803-97-0
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| Related CAS # |
Metolachlor;51218-45-2
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| PubChem CID |
71750717
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| Appearance |
Light yellow to yellow liquid
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| Density |
1.1±0.1 g/cm3
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| Boiling Point |
406.8±45.0 °C at 760 mmHg
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| Flash Point |
199.8±28.7 °C
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| Vapour Pressure |
0.0±0.9 mmHg at 25°C
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| Index of Refraction |
1.533
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| LogP |
3
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
6
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| Heavy Atom Count |
19
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| Complexity |
285
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| Defined Atom Stereocenter Count |
0
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| SMILES |
ClCC(N(C1C(C)=CC=CC=1CC)C([2H])(C([2H])([2H])[2H])C([2H])([2H])OC)=O
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| InChi Key |
WVQBLGZPHOPPFO-XCPSXBTFSA-N
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| InChi Code |
InChI=1S/C15H22ClNO2/c1-5-13-8-6-7-11(2)15(13)17(14(18)9-16)12(3)10-19-4/h6-8,12H,5,9-10H2,1-4H3/i3D3,10D2,12D
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| Chemical Name |
2-chloro-N-(2-ethyl-6-methylphenyl)-N-(1,1,1,2,3,3-hexadeuterio-3-methoxypropan-2-yl)acetamide
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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) |
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
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| 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 | 3.4503 mL | 17.2515 mL | 34.5030 mL | |
| 5 mM | 0.6901 mL | 3.4503 mL | 6.9006 mL | |
| 10 mM | 0.3450 mL | 1.7251 mL | 3.4503 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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