104206-82-8 Usage
Description
Mesotrione (2-[4-(methylsulfonyl)-2-nitrobenzoyl]-cylohexane-1,3-dione) is a selective herbicide which is also referred to as Callisto and Tenacity (trademarks). It was introduced to the market in 2001 for use in maize plantations as a control measure against grass and broad-leaved weeds. Mesotrione is a triketone herbicide which was formulated after the discovery of the naturally occurring phytotoxin leptospermone secreted by the Callistemon citrinus plant.
Chemical and Physical Properties
Mesotrione is a light yellow opaque solid with a faint pleasant odour. It dissolves at a rate of 2.2 g/l at 200 C in unbuffered water whose pH is 4.8. It also dissolves in n-heptane <0.5, xylene 1.6, toluene 3.1, methanol 4.6, ethyl acetate 18.6, 1,2-dichloroethane 66.3, acetone 93.3, and in acetonitrile 117.0, all in g/l at 200 C.
Mesotrione has a molecular weight of 339.318 g/mol, a monoisotopic mass of 339.041 g/mol and an exact mass of 339.041 g/mol. It has a heavy atom count of 23 and a complexity of 627.
Mechanism of Action
Studies indicate that the toxic influence of the compound can be attributed to high plasma concentration levels of tyrosine which is resultant of inhibition by 4-hydroxyphenylpyruvate dioxygenase (HPPD). HPPD is an essential constituent of the biochemical route that aids the conversion of tyrosine to alpha-tocopherol and plastoquino\ne.
Mesotrione is a highly potent agonist of HPPD against Arabidopsis thaliana, which is indicated by the Ki figure of c 6-18 pM. It is readily absorbed by weed species after foliar application and it is widely distributed to various parts of the plant through basipetal and acropetal movement.
Maize crops are generally tolerant to Mesotrione as a result of selective metabolism by the plant. The compound may take a relatively long time to be absorbed in some weed species hence Mesotrione is applied as a selective herbicide in maize plantations.
The plasma half-life of the compound is approximately 1 hour.
Preparation
Mesotrione is synthesized through the reaction of acetyl chloride with 3-methylmercaptonitrobenzene with aluminum trichloride as the catalyst. The relative ketone is oxidized with sodium oxychloride which results in the 4-methylsulfonyl compound, which is condensed with cyclohexane-1,3-dione to obtain the respective enol ester. The latter is reorganized to the appropriate form of the product with potassium cyanide with triethylamine as the catalyst.?
Mesotrione is available as a soluble solid or concentrates, as a pressurized liquid, a ready to use solution, soluble concentrate, emulsifiable concentrate, water dispersible granules and in granular form.?
Some of its premix partners may include terbuthylazine, Rimsulfron, Nicosulfron, S-Metolachlor, Glyphosphate and Atrazine.
Consumption
A study indicated that the total usage of the compound in the last 5 years is primarily in corn, which accounts for about 98% of the total acres treated and the total pounds of the applied Mesotrione. Field corn accounts for the highest percentage of the treated crops in regards to the acres treated and the acreage of crops grown at 20.2%.
Precautionary Statements
The applicator should put on protective gear when handling Mesotrione concentrate or contaminated surfaces. It is recommended that one avoids eating, drinking or smoking while handling the product and that one should always wash off any splashes that come into contact with the skin immediately.?
During the application process, the sprayer should ensure that the machine is calibrated appropriately, the nozzles are in a matched set and the machine is adjusted to the respective level of the crop. The concentrates should not be left in the sprayer for extended periods of time.?
Mesotrione may cause mild or acute eye irritation. However, it is not a dermal irritant.
Uses
Different sources of media describe the Uses of 104206-82-8 differently. You can refer to the following data:
1. Mesotrione is a herbicide that works by inhibiting 4-hydroxyphenylpyruvate dioxygenase (HPPD), a crucial enzyme for the biosynthesis of carotenoid in plants. Mesotrione is also a synthetic analog of l
epospermone.
2. Herbicide.
Definition
ChEBI: An aromatic ketone that is cyclohexa-1,3-dione in which one of the hydrogens at position 2 is substituted by a 4-(methanesulfonyl)-2-nitrobenzoyl group.
Check Digit Verification of cas no
The CAS Registry Mumber 104206-82-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,0,4,2,0 and 6 respectively; the second part has 2 digits, 8 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 104206-82:
(8*1)+(7*0)+(6*4)+(5*2)+(4*0)+(3*6)+(2*8)+(1*2)=78
78 % 10 = 8
So 104206-82-8 is a valid CAS Registry Number.
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
104206-82-8Relevant articles and documents
Method for preparing triketone compound through continuous flow
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Paragraph 0023-0025, (2021/09/08)
The invention relates to a method for preparing a triketone compound through continuous flow, which uses substrate acyl chloride and 1, 3 - cyclohexanedione as a raw material and is subjected to esterification. The method is mild in condition, simple to operate, good in stability and high in reliability. Utilize continuous flow can accurate control dwell time, the good characteristics of mass transfer heat transfer, easily realize accurate control, restrain the production of side reaction, and reaction yield is high. The method has remarkable innovation meaning and economic value, is easy for industrialization and has a wide prospect.
Selective oxidation of (hetero)sulfides with molecular oxygen under clean conditions
Liu, Kai-Jian,Deng, Ji-Hui,Yang, Jie,Gong, Shao-Feng,Lin, Ying-Wu,He, Jun-Yi,Cao, Zhong,He, Wei-Min
supporting information, p. 433 - 438 (2020/02/13)
The development of eco-friendly and switchable catalytic systems for the conversion of a sole raw-material into distinct high-value products is a particularly attractive concept and a daunting synthetic challenge. In the present work, the first example of efficient and selective oxidation of sulfides to sulfones and sulfoxides using molecular oxygen under clean conditions was established.
Synthesis process of mesotrione
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Paragraph 0038-0052; 0057-0065, (2019/10/04)
Belonging to the field of herbicide original drug preparation, the invention discloses a synthesis process of mesotrione. The process includes the steps of: (1) catalytic oxidation: taking 2-nitro-4-methylsulfonyl toluene as the raw material, and adopting oxygen as the oxidant to generate 2-nitro-4-methylsulphonylbenzoic acid under the catalysis of a manganese oxide octahedral molecular sieve loaded heteropolyacid-transition metal salt; (2) acyl chlorination: subjecting 2-nitro-4-methylsulphonylbenzoic acid to acyl chlorination to generate 2-nitro-4-methylsulfonylbenzoyl chloride; (3) condensation: carrying out condensation reaction on 2-nitro-4-methylsulfonylbenzoyl chloride and 1, 3-cyclohexanedione to obtain an enol ester intermediate reaction solution; (4) rearrangement: subjecting the enol ester intermediate to enol ester rearrangement under the catalysis of a rearrangement catalyst to obtain a crude product reaction solution; and (5) refining: refining the crude product reaction solution to obtain a mesotrione finished product. The process provided by the invention optimizes the reaction conditions, the conversion rate of each step is high, the yield and purity of the product are high, the whole production process does not involve hypertoxic materials, and the safety is high.