Flucarbazone Sodium

• CAS: 181274-17-9
• Catalog Number: ACM181274179
• Category: Main Products
• Molecular Weight: 418.28
• Molecular Formula: C₁₂H₁₀F₃N₄NaO₆S
• Synonyms: sodium [(4,5-dihydro-3-methoxy-4-methyl-5-oxo-1H-1,2,4-triazol-1-yl)carbonyl]{[2-(trifluoromethoxy)phenyl]sulfonyl}azanide; sodium,(3-methoxy-4-methyl-5-oxo-1,2,4-triazole-1-carbonyl)-[2-(trifluoromethoxy)phenyl]sulfonylazanide; BAY-MKH 6562; MKH 6562; Flucarbazone sodium; Flucarbazone-sodium; SJO 0498; sodium (3-methoxy-4-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazole-1-carbonyl)[2-(trifluoromethoxy)benzenesulfonyl]azanide
• IUPAC Name: sodium;(3-methoxy-4-methyl-5-oxo-1,2,4-triazole-1-carbonyl)-[2-(trifluoromethoxy)phenyl]sulfonylazanide
• SMILES: CN1C(=NN(C1=O)C(=O)[N-]S(=O)(=O)C2=CC=CC=C2OC(F)(F)F)OC.[Na+]
• InChI Key: UOUXAYAIONPXDH-UHFFFAOYSA-M
• Boiling Point: 463.7ºC at 760mmHg
• Flash Point: 234.2ºC
• EC Number: 605-921-7
• Exact Mass: 418.01700

Case Study

Study on the properties of flucarbazone-sodium in soil

Eliason, Rachael, et al. Weed Science 52.5 (2004): 857-862.

flucarbazone-sodium is a novel herbicide with high bioactivity at low concentrations. To elucidate its potential genetic effects and crop damage, the behavior of flucarbapone in six soils from Western Canada was investigated in the laboratory. A sensitive bioassay was developed for the detection of flucarbapone. Among five crops, Oriental mustard showed the highest degree of root and stem inhibition due to the presence of flucarbapone in the soil. The mustard root inhibition assay detected concentrations as low as 1 mg of flucarbapone. This bioassay was used to determine the phytotoxicity and persistence of flucarbapone.
Flucarbapone with a purity of 99.1% was used. Bottles were prepared by transferring 0.01 g of flucarbapone to approximately 50 mL of methanol in a 1 L volumetric liquid and then filling with water. A series of standard solutions containing flucarbapone were prepared at concentrations of 0, 0.1, 0.3, 0.5, 1.0, and 2.0 mg/L. Each solution, in 0.75 mL volumes, was used to prepare 0, 1, 3, 5, 10, and 20 mg of flucarbazone for 75 g of soil. 0.75 mL of each flucarbazone solution was transferred to a calculated amount of water and then evenly mixed into the soil in plastic dishes. The (untreated) soil was controlled to contain only water, reaching the specified FC percentage. The moist and thorny soil was left overnight, covered with plastic film to allow equilibration. The soil was again hand-mixed and transferred to foam cups, each containing five pre-germinated seeds. The soil surface was then covered with 15 g of plastic beads to prevent drying. The plants were grown at room temperature under a fluorescent canopy for 5 days, watered daily to 100% FC by adding the predetermined weight of water.

Research on the resistance mechanism of wild oats to flucarbazone-sodium

Sun, Ying, et al. BMC Plant Biology 24.1 (2024): 1073.

Wild oats (Avena fatua L.) are self-pollinating, ahexaploid plant belonging to the Gramineae family. This is a noxious weed that primarily harms crops such as wheat. In recent years, the control efficiency of flucarbazone-sodium against wild oats has declined in some areas. The flucarbazone-sodium resistance mechanism in *A. fatua* is mediated by NTSR, not TSR. The CYP92A6 and Aldo/ketoreductase families were found to be potentially involved in NTSR metabolism in the *A. fatua* population, supporting further functional studies. These results will serve as a data resource for further research on the molecular mechanisms of *Fatua* and flucarbazone-sodium.
An ALS-resistant *A. fatua* population (R population) was identified. Whole-plant reaction assays showed that the R population exhibited moderate resistance (5.9-fold) to flucarbazone-sodium. Malathion pretreatment significantly reduced resistance to flucarbakedin-sodium in the R population. Known mutation sites and relative expression of ALS genes, which confer resistance to ALS inhibitors, were not found in the R population. Following flucarbakedin-sodium treatment, the expression of eight genes related to metabolic enzymes was investigated using quantitative real-time PCR (qRT-PCR). CYP92A6 and the Aldo/ketoreductase family showed high expression levels in the R population after flucarbakedin-sodium application.

Flucarbazone-sodium and its metabolites determined and released in wheat and soil using LC-MS/MS

Xue, J., et al. International Journal of Environmental Analytical Chemistry 94.5 (2014): 479-492.

A rapid analytical method based on extraction with an acetonitrile/water mixture and cleanup with graphitized carbon black was developed for the analysis of flucarbazone-sodium and its metabolites. The determination of both compounds in wheat and soil samples was performed using liquid chromatography-tandem quadrupole mass spectrometry. The average recovery of flucarbazone-sodium ranged from 87.0% to 99.6%, and the recovery of metabolites in wheat, straw, grain, and soil samples ranged from 83.2% to 102.8%. The results showed that the dissipation rate of flucarbazone-sodium followed first-order kinetics, with a half-life of 1.5 to 3 days in wheat plants and 8 to 14 days in soil. This work contributes to setting maximum residue limits for flucarbazone-sodium and reveals the transformation of these two compounds in soil.
Each experimental treatment included three replicate plots; each plot had an area of 30 square meters. Flucarbazone-sodium formulation (35% suspension concentrate) was sprayed onto wheat crops and soil at 79 g a.i./hectare (1.5 times the recommended dose) to study the dissipation of flucarbazone-sodium. Terminal residue experiments were conducted in triplicate at doses of 52.5 g a.i./hectare (recommended dose) and 79 g a.i./hectare (1.5 times the recommended dose). Plots of the same area but without flucarbazone-sodium application were used as control areas for comparison, separated by irrigation channels.

Basic research on the resistance targets of flucarbazone-sodium

Li, Qi, et al. Chilean journal of agricultural research 82.3 (2022): 493-501.

Japanese brome (Bromus japonicus Houtt.) is an annual weed widely distributed in winter wheat fields (Triticum aestivum L.). A population of B. japonicus (TJ06) suspected of resistance to acetolactate synthase (ALS) inhibitors was discovered. This study confirmed that the TJ06 population of Japanese brome has evolved a high level of resistance to flucarbazone-sodium, and revealed the molecular mechanism of this resistance through an Asp-376-Glut mutation in the ALS gene. These results indicate that continuous and intensive application of flucarbazone-sodium has led to the development of resistance in B. japonicus in China, therefore, integrated weed management systems are crucial for the control of B. japonicus in wheat fields.
The TJ06 population exhibited 66.7-fold resistance to flucarbazone-sodium and showed significant cross-resistance to two other ALS-inhibiting herbicides. The 50% plant growth reduction (GR50) values for pyroxasulfone and mesosulfuron-methyl were 28.72 and 39.44 g ai ha⁻¹, respectively. In in vitro ALS activity assays, the concentration of flucarbazone-sodium required to inhibit 50% of TJ06 ALS activity was 11.3 times higher than that of the susceptible population (TJ01), which was highly correlated with the whole-plant response experiments, indicating that the Asp-376-Glut mutation leading to resistance reduced the sensitivity of the ALS enzyme to flucarbazone-sodium.

Custom Q&A

What is the molecular formula of flucarbazone sodium?

The molecular formula of flucarbazone sodium is C12H10F3N4NaO6S.

What is another name for flucarbazone sodium?

Another name for flucarbazone sodium is Flucarbazone-sodium.

What is the molecular weight of flucarbazone sodium?

The molecular weight of flucarbazone sodium is 418.28 g/mol.

What is the role of flucarbazone-sodium?

Flucarbazone-sodium is an EC 2.2.1.6 (acetolactate synthase) inhibitor, a herbicide, and an agrochemical.

How is flucarbazone-sodium used?

Flucarbazone-sodium is used as a herbicide to control grass weeds in cereal crops.

Is flucarbazone sodium approved for use within the European Union?

No, flucarbazone sodium is not approved for use within the European Union.

What is the IUPAC name of flucarbazone sodium?

The IUPAC name of flucarbazone sodium is sodium;(3-methoxy-4-methyl-5-oxo-1,2,4-triazole-1-carbonyl)-[2-(trifluoromethoxy)phenyl]sulfonylazanide.

What is the InChIKey of flucarbazone sodium?

The InChIKey of flucarbazone sodium is UOUXAYAIONPXDH-UHFFFAOYSA-M.

What is the canonical SMILES of flucarbazone sodium?

The canonical SMILES of flucarbazone sodium is CN1C(=NN(C1=O)C(=O)[N-]S(=O)(=O)C2=CC=CC=C2OC(F)(F)F)OC.[Na+].

What is the CAS number of flucarbazone sodium?

The CAS number of flucarbazone sodium is 181274-17-9.