(4-(METHYLSULFONYL)-2-NITROBENZOYL)-1,3-CYCLOHEXANEDIONE
2-(4-Mesyl-2-nitrobenzoyl)-1,3-cyclohexanedione
CAS: 104206-82-8
Molecular Formula: C14H13NO7S
(4-(METHYLSULFONYL)-2-NITROBENZOYL)-1,3-CYCLOHEXANEDIONE - Names and Identifiers
| Name | 2-(4-Mesyl-2-nitrobenzoyl)-1,3-cyclohexanedione |
| Synonyms | MESOTRION MESOTRIONE MESOTRION, PESTANAL mesotrione (bsi, pa iso) 2-(4-MESYL-2-NITROBENZOYL)-1,3-CYCLOHEXANEDIONE 2-(4-Mesyl-2-nitrobenzoyl)-1,3-cyclohexanedione (4-(METHYLSULFONYL)-2-NITROBENZOYL)-1,3-CYCLOHEXANEDIONE 2-[4-(methylsulfonyl)-2-nitrobenzoyl]cyclohexane-1,3-dione 2-[4-(methylsulfonyl)-2-nitrobenzoyl]-1,3-cyclohexanedione 1,3-Cyclohexanedione, 2-4-(methylsulfonyl)-2-nitrobenzoyl- mesotrione 2-[4-(methylsulfonyl)-2-nitrobenzoyl]-1,3-cyclohexanedione |
| CAS | 104206-82-8 |
| InChI | InChI=1/C14H13NO7S/c1-23(21,22)8-5-6-9(10(7-8)15(19)20)14(18)13-11(16)3-2-4-12(13)17/h5-7,13H,2-4H2,1H3 |
| InChIKey | KPUREKXXPHOJQT-UHFFFAOYSA-N |
(4-(METHYLSULFONYL)-2-NITROBENZOYL)-1,3-CYCLOHEXANEDIONE - Physico-chemical Properties
| Molecular Formula | C14H13NO7S |
| Molar Mass | 339.32 |
| Density | 1.474±0.06 g/cm3(Predicted) |
| Melting Point | 165° |
| Boling Point | 643.3±55.0 °C(Predicted) |
| Flash Point | 342.9°C |
| Vapor Presure | 1.93E-16mmHg at 25°C |
| Appearance | White to yellow powder |
| BRN | 8999656 |
| pKa | pKa (20°): 3.12 |
| Storage Condition | Inert atmosphere,Room Temperature |
| Refractive Index | 1.583 |
| MDL | MFCD04112617 |
(4-(METHYLSULFONYL)-2-NITROBENZOYL)-1,3-CYCLOHEXANEDIONE - Risk and Safety
| Hazard Symbols | N - Dangerous for the environment |
| Risk Codes | 50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. |
| Safety Description | S60 - This material and its container must be disposed of as hazardous waste. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. |
| UN IDs | UN 3077 |
| WGK Germany | 2 |
| Toxicity | LD50 in rats (mg/kg): >5000 orally; >2000 dermally; LC50 in rats (mg/l): >5 by inhalation; LC50 (96 hr) in bluegill sunfish, rainbow trout (mg/l): >120, >120 |
(4-(METHYLSULFONYL)-2-NITROBENZOYL)-1,3-CYCLOHEXANEDIONE - Reference Information
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| Overview | The original drug of methyl sulfonone is a brown or light yellow solid, the English common name is mesotrion, and the chemical name is 2-(4-methylsulfonyl -2-Nitro-benzoyl) cyclohexan-1, 3-dione, is a new triketone herbicide developed by Zeneca Agrochemical Company, it can be used to prevent and remove annual broad-leaved weeds and several gramineous weeds before or after seedlings in corn fields, including Xanthium, Abutilon, Chenopodium, Amaranthus, Polygonum, Solanum nigrum, Ambrosia trifolia, etc. Most important broad-leaved weeds in the field and some gramineous weeds such as young barnyard, crabgrass, Setaria, Brachium, etc. |
| Drug overview | Name: Methohexone English name: mesotrion alias: Sulfonone, Mistone Chemical name: 2-(4-Methyl -2-Nitro-benzoyl) Cyclohexane -1, 3-dione Chemical formula: C14H13NO7S Molecular weight: 339.32 Figure 1 is the structural formula of sulfoxone |
| physical and chemical properties | brown or light yellow solid, melting point 165 ℃, density 1.46 g/ml(20 ℃), vapor pressure 4.27 × 10-8mmHg (20 ℃). Soluble in dichloromethane, acetonitrile and acetone, it is a weak acid, pKa3.12(20 ℃), because of its weak acidity, so the degree of ionization varies with pH, water solubility is pH-dependent, from 20 ℃ 2.2g/L(pH4.8), 15g/L (pH6.9) to 22g/L(pH9.0),pH4~9 resistant to hydrolysis. |
| Preparation method | Using lower-cost p-methylbenzoyl chloride as the starting material, sodium chloroacetate instead of dimethyl sulfate and other highly toxic reagents as methylation reagents, the important intermediate of the reaction is synthesized, p-methylsulfoxyltoluene, and this product is synthesized through nitration, oxidation, chlorination, condensation and other reactions. The synthesis is divided into 5 steps, including methylation, nitrification, oxidation, chlorination and rearrangement. 1. methylation reaction add 35.0g NaHCO3, 27.0g Na2SO3 and 100.0 mL of water to a 1 L four-mouth flask equipped with a thermometer and a magnetic stirrer, slowly stir and raise the temperature to completely dissolve the solid, slowly add 40.0g of p-toluenesulfonyl chloride (a), after addition, continue to slowly heat to 75 ℃, stir and react at constant temperature for 3 h to obtain sodium p-toluenesulfonite (B), and add 35, after heating and refluxing for 18 h, the reaction solution is taken out and cooled while the reaction is complete, hydrochloric acid is acidified, cooled and filtered to obtain crude product, recrystallized with ethanol, and filtered and dried to obtain 32.3g of p-methylsulfonyltoluene (c) with 90.5% yield. the methylation reaction process is shown in fig. 2. fig. 2 shows the methylation reaction process 2. nitrification reaction 25.0g p-methylsulfonyl toluene (c) is added into the reaction bottle, concentrated sulfuric acid with 35.0 mL 98% is slowly added dropwise under good stirring, and cooled by ice water bath. After the droplet addition of concentrated sulfuric acid is completed, the mixed acid (12.0 mL 65% concentrated nitric acid/12.0 m L 98% concentrated sulfuric acid) is slowly added dropwise at 5 ℃ of the system, the dropwise addition is completed, after stirring for 3 h at room temperature, a large amount of ice water is added into the flask, the material is taken out after stirring for 30 min, the obtained solid is filtered, washed with water, and dried at 50 ℃, 28.4g of 2-nitro-4-methylsulfonyltoluene (d) was obtained with 89.6% yield. The reaction process is shown in Figure 3. fig. 3 is the nitration reaction process 3. oxidation reaction 20.0g 2-nitro -4-methylsulfonyl toluene (d) and a certain amount of 70% sulfuric acid are added into the reaction bottle. after the solid is completely dissolved, a small amount of V2O5 is added, and 50.0 mL of concentrated nitric acid is slowly added into the reaction bottle dropwise. after the dropwise addition is completed, stirring at room temperature for 1 h, after that, the reaction was stirred at 150 ℃ for 10h in a high-pressure reactor. After the reaction was completed, ice water was added to the system for cooling crystallization and filtering to obtain crude products. The crude product was added to sodium hydroxide solution, dissolved and filtered, hydrochloric acid was added dropwise to the filtrate until the precipitation was complete, and filtered and dried to obtain 19.8g of 2-nitro-4-methylsulfone benzoic acid (e) with 86.9% yield. The reaction process is shown in Figure 4. fig. 4 shows the oxidation reaction process 4. chlorination reaction 10.0g of 2-nitro -4-sulfone benzoic acid (e) and 50.0 mL of thionyl chloride are added to the reaction bottle, stirred and dissolved, 5.0 mL of DMF is added, reflux reaction is carried out for 5 h, light brown solution is obtained after the reaction is completed, 3.0 mL of ethanol is added to the remaining liquid after distilled out of light components, cooling crystallization gave light yellow crystal: 10.3g of 2-nitro-4-methylsulfobenzoyl chloride (g) with 96.2% yield. The reaction process is shown in Figure 5. fig. 5 is the chlorination reaction process 5. condensation rearrangement reaction 10.3g 2-nitro -4-methanesulfonyl benzoyl chloride (g) and 5 g 1,3-cyclohexanedione (h) are added into the reaction bottle, 30 mL dichloroethane is added as solvent, stirred and dissolved, and 18.0 mL ethylenediamine is added as acid binding agent, and condensation reaction is carried out at normal temperature for 1.5 h, after enol ester is formed, 5.0 mL of acetonitrile is added as rearrangement catalyst and a small amount of acid binding agent, and the enol product is fully converted into ketone product by stirring for 3 h at room temperature. After the reaction is completed, 200 mL of water is added, stirred for 30 min, then left to layer, after the organic layer removes the solvent, recrystallized with methanol, filtered and dried to obtain 12.3g of yellow solid methyl sulfoxone (j) with a yield of 90.4%. The reaction process is shown in Figure 6. Figure 6 shows the condensation rearrangement reaction process |
| Action characteristics | Methopropoxone is an effective inhibitor of HPPD (4-hydroxyphenylpyruvate dioxidase). This enzyme is widely present in various organisms and catalyzes the initial reaction of plastoquinone and tocopherol biosynthesis (Figure 7). The optimum pH of this enzyme in phosphate buffer is 7.3, but the activity range is wide. When the temperature is increased from 23 ℃ to the optimum temperature of 30 ℃, the activity increases by 2 times. The molecular mass of HPPD in corn is 43kDa, and the enzyme activity requires reducing agent glutathione, dichlorophenol or ascorbic acid. In the presence of ascorbic acid, the enzyme activity in maize increased 2 times. In plants, tyrosine metabolism is an important process. Its metabolite urinic acid is a precursor substance for the synthesis of photosynthetic pigment quinone and tocopherol. Urinic acid biosynthesis includes a decarboxylation stage, double oxidation and pyruvate side chain rearrangement. This complex reaction is induced by HPPD. HPPD is inhibited, resulting in tyrosine accumulation and plastoquinone failure in plant meristem, and plant albino and gradual death. fig. 7 shows the biosynthesis path of HPPD, α-tocopherol and plastoquinone in plants after spraying methyl sulfaxone on stems and leaves, weeds are rapidly absorbed, conducted upward and downward to reach meristem, resulting in albinization and death of weeds. The reasons for the resistance of maize are:(1) the absorption of maize leaves is slower than that of weeds, and the absorption and conduction dose is low. The 48% of the absorption of quinoa after spraying is conducted from the treated leaves to other parts, while the conduction of maize to other parts is only 14%;(3) Corn can rapidly metabolize mesotrione into inactive compounds, especially through the 4-hydroxylation catalyzed by cytochrome P450. Two degradation products MNBA and AMBA were measured in plants and soil. According to the analysis of the US Environmental Protection Agency, AMBA only exists in soil and water (Figure 2). MNBA was measured in corn grains, stems and leaves and sugarcane, while MNBA and AMBA were measured in soil and water. The determination limits were 0.1 mg/kg for crops, 0.005 mg/kg for soil and 0.10 μg/L for water. Fig. 8 shows the transition of mesaloxone to MNBA and AMBA |
| usage | used for soil surface treatment before budding in corn field or spraying after seedling, absorption of seeds, young roots, young buds and leaves, conduction of xylem and phloem, dosage before bud 200~300g/hm2, and 100~150g/hm2 after seedling. considering the climatic characteristics of "ten years and nine spring droughts" in the spring corn region in northern China, it is suggested that mesohexone should be sprayed with stems and leaves. 70~80g/hm2 + 1% methyl esterified vegetable oil can achieve satisfactory weeding effect. The summer corn in North and Central China can be treated with soil and sprayed with stems and leaves. Mesaloxone has strong computability in use, and the pre-bud treatment can be mixed with atrazine, acetochlor, metolachlor, etc. After seedling, stem and leaf spray can be mixed with nicosulfuron (Yunongle), sulfuron-methyl (rimsuluron), atrazine, bromonitrile, etc. |
| application | can be used to control annual broad-leaved weeds and several gramineous weeds before or after corn bud, mainly including cocklebur, Abutilon, Chenopodium, Amaranthus, Polygonum, Solanum nigrum, Tricolata and other important broad-leaved weeds in the field, as well as some gramineous weeds such as young barnyard grass, crabgrass, Setaria barniculi, Brachium, etc. |
| Uses | Methosulforone Features: Methosulforone is an effective inhibitor of HPPD (4-hydroxyphenylpropanoic acid dioxidase). This enzyme is widely present in various organisms and catalyzes the initial reaction of plasmoquinone and tocopherol biosynthesis. The optimum pH of this enzyme in phosphate buffer is 7.3, but the activity range is wide. When the temperature is increased from 23 ℃ to 30 ℃, the activity is increased by 2 times. HPPD is inhibited, resulting in tyrosine accumulation and plastoquinone failure in plant meristem. Plants are albino and gradually die. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 02:00:05
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