CN106748919A - A kind of synthesis technique of mesotrione - Google Patents
A kind of synthesis technique of mesotrione Download PDFInfo
- Publication number
- CN106748919A CN106748919A CN201610994931.7A CN201610994931A CN106748919A CN 106748919 A CN106748919 A CN 106748919A CN 201610994931 A CN201610994931 A CN 201610994931A CN 106748919 A CN106748919 A CN 106748919A
- Authority
- CN
- China
- Prior art keywords
- added dropwise
- product
- reaction
- nitro
- added
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/04—Preparation of sulfones; Preparation of sulfoxides by reactions not involving the formation of sulfone or sulfoxide groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The synthesis technique of a kind of high income, product purity mesotrione high, including step：After in the nitration reaction kettle addition concentrated sulfuric acid, to methylsulfonyltoluene and water, the uniform nitric acid that is added dropwise carries out nitration reaction in 4~5 hours, and 60~70 minutes are incubated after completion of dropping, obtains nitrification liquid；Catalyst V2O5 and boron nitride powder are added after nitrification liquid is imported into oxidizing reactor, then 1240~1290kg nitric acid is added dropwise, and controlling reaction temperature is 142~146 DEG C；12 hours are incubated after completion of dropwise addition；After reaction solution is cooled into 100 degree, 48~50 degree are cooled to after adding water again, then press filtration obtains oxidation product, oxidation product is rinsed with water circulation；It is dried to obtain the methyl sulfonylbenzoic acid of 2 nitro 4 at 55~70 DEG C after oxidation product is repeatedly refined；Thionyl chloride is added in acyl chloride reaction kettle, then puts into the methyl sulfonylbenzoic acid of 2 nitro 4, DMF to carry out temperature rising reflux reaction, reaction carries out condensation rearrangement again after 3~4 hours.
Description
Technical field
The invention belongs to chemical field, and in particular to a kind of synthesis technique of mesotrione.
Background technology
Mesotrione action target is p-hydroxyphenypyruvate dioxydenase (HPPD), is mainly used in preventing and kill off corn field
Broad leaved weed and grassy weed, with herbicidal spectrum it is wide, Environmental compatibility is good, very low to mammal and aquatic toxicity,
It is fool proof to corn and to rear stubble rotation crop without characteristics such as poisoning, it is preceding with the very big market demand and good application
Scape.Additionally, mesotrione to prevent and kill off anti-three pyridine especially effective with the weeds of anti-sulfonylureas, weeds are in it and these type herbicides
Between do not exist cross resistance, this just provides convenience to herbicide Fruit variety in crop rotation.
At present, mesotrione is typically carried out being condensed rearrangement reaction system by intermediate 2- nitro -4- methylsulphonyl benzoyl chlorides
It is standby.And the synthesis of intermediate 2- nitro -4- methylsulphonyl benzoyl chlorides has various methods.At present, further closed by these methods
Overall reaction yield into mesotrione is preferable, up to 78% or so, but still has larger room for promotion.And product purity is low, very
The rare mesotrione in accordance with quality requirement, i.e. product purity is poor, while in the conjunction of 2- nitro -4- methylsulphonyl benzoyl chlorides
Cheng Zhong, various nitre compound impurities of generation increased the danger of industrialized production to next step synthesizing methyl sulphur humulone.
The content of the invention
To solve the above problems, the invention provides the synthesis technique of a kind of high income, product purity mesotrione high.
The synthesis technique of mesotrione provided by the present invention, including step：
Nitrification：In 1400~1500kg of the nitration reaction kettle addition concentrated sulfuric acid, to 350~360kg of methylsulfonyltoluene and water 300
After~330kg, the uniform nitric acid that 200~210kg is added dropwise carries out nitration reaction in 4~5 hours, and 60~70 are incubated after completion of dropping
Minute, obtain nitrification liquid；
Oxidation：Will nitrification liquid import oxidizing reactor after add 1~10 micron of catalyst V2O5 and 15~20kg
Boron nitride powder, then 1240~1290kg nitric acid is added dropwise, and controlling reaction temperature is 142~146 DEG C；1- is incubated after completion of dropwise addition
2 hours；After reaction solution is cooled into 100 degree, 48~50 degree are cooled to again after adding water 800~1000kg, then press filtration is obtained
Oxidation product, rinsing oxidation product is circulated with 1000~1100kg of water；By it at 55~70 DEG C after oxidation product is repeatedly refined
Under be dried to obtain 2- nitro -4- methyl sulfonylbenzoic acids；
Chloride：Thionyl chloride is added in acyl chloride reaction kettle, then puts into 2- nitro -4- methyl sulfonylbenzoic acids, DMF
To carry out temperature rising reflux reaction, separated goes out thionyl chloride after reacting 3~4 hours, obtains 2- nitro -4- mesyl benzene first
Acyl chlorides；
Condensation is reset：After the 2- nitro -4- methylsulphonyl benzoyl chloride dichloromethane that will be obtained dissolves well, it is cooled to
35~40 DEG C, the 1 of 240~250kg of input, hydroresorcinol, uniform 90~100kg triethylamines that are added dropwise enter in 60~80 minutes
Row esterification condensation；210~230kg acetone cyanohydrins are added, 100~110kg triethylamines are added dropwise carries out rearrangement reaction, then adds hydrochloric acid
It is 4.5~5.0 to be adjusted to pH, point liquid washing, is distilled to reclaim dichloromethane, and then blowing, suction filtration obtain crude product sulphur humulone；While hot will
In the crude product sulphur humulone input refining reaction kettle that suction filtration goes out, stirred 20~40 minutes at 50~55 DEG C, suction filtration after blowing, mother liquor
Enter the distillation of methyl alcohol distillation still refined to reclaim methyl alcohol, solid product is obtained into mesotrione finished product after drying, air-flow crushing.
Its in addition to high income, product purity are high, due to the reuse to oxidation mother liquor, it is possible to reduce the use of catalyst
Amount, and the product ton consumption of fresh water can be reduced, while reducing waste water；And big shortening, reacting balance are easy to the time required to reaction
Control.In addition, the presence of boron nitride powder can promote crystallization further to shorten the reaction time, and during mother liquor reuse, part nucleation
Agent can also play a part of to promote crystallization in oxidation step again.
Preferably, in the oxidation step, the consumption of catalyst V2O5 is 7~7.5kg.
Preferably, it is uniform first in 20~22 hours that nitric acid 890 is added dropwise when nitric acid is added dropwise in the oxidation step
~920kg, while controlling reaction temperature is 144~146 degree；It is uniform in 15.5~17 hours again that 350~370kg nitre is added dropwise
Acid, while controlling reaction temperature is 142-144 degree；1~2 hour is incubated after completion of dropwise addition.So, reaction can further be reduced
Accessory substance, to improve product purity.
Preferably, when the oxidation product is refined, pH value is adjusted to 8.0~9.0 to addition NaOH solution in oxidation product,
To dissolve oxidation product, it is 55~60 DEG C that temperature is controlled in adition process；Then blowing centrifugation while hot, is added dropwise hydrochloric acid and adjusts pH value
To 1~2, kept for 30~50 minutes in the range of 55~60 DEG C of temperature, be centrifuged after being cooled to 35 DEG C, rinsing, obtain final product refined 2-
Nitro -4- methyl sulfonylbenzoic acids.
Specific embodiment
Embodiment 1
After in 98% concentrated sulfuric acid 1400kg of nitration reaction kettle addition, to methylsulfonyltoluene 360kg and water 330kg, in 4 hours
Uniform 98% nitric acid that 200kg is added dropwise carries out nitration reaction, and 60 minutes are incubated after completion of dropping, obtains nitrification liquid；
Nitrification liquid is imported 7kg catalyst V2O5 and 20kg granularities are added after oxidizing reactor in 1~10 micron of nitridation
Boron powder, it is uniform in 20 hours that 68% nitric acid 920kg is added dropwise after being warming up to 142 degree, while controlling reaction temperature is 144 degree；
50% nitric acid of 370kg was uniformly added dropwise in 17 hours again, while controlling reaction temperature is 142 degree；Insulation 2 is small after completion of dropwise addition
When.After reaction solution is cooled into 100 degree, 48 degree are cooled to again after adding water 800kg, then press filtration obtains oxidation product, uses water
1000kg circulation rinsing oxidation products；To adding NaOH solution to adjust pH value to 8.0 in oxidation product, to dissolve oxidation product,
It is 55 DEG C that temperature is controlled in adition process；Then blowing centrifugation while hot, is added dropwise hydrochloric acid and adjusts pH value to 1, is kept at 55 DEG C of temperature
50 minutes, it is centrifuged after being cooled to 35 DEG C, rinsed, obtains final product refined 2- nitro -4- methyl sulfonylbenzoic acids；By it after refining for three times
Dried at 70 DEG C；Add thionyl chloride in acyl chloride reaction kettle, then put into 2- nitro -4- methyl sulfonylbenzoic acids, DMF with
Temperature rising reflux reaction is carried out, separated goes out thionyl chloride after reacting 3~4 hours, that is, obtain 2- nitro -4- mesyl benzene first
Acyl chlorides；
After the 2- nitro -4- methylsulphonyl benzoyl chloride dichloromethane that will be obtained dissolves well, 35 DEG C, input are cooled to
The 1 of 240kg, hydroresorcinol, the uniform 90kg triethylamines that are added dropwise carry out esterification condensation in 60 minutes；Add 210kg acetone
Cyanalcohol, dropwise addition 100kg triethylamines carry out rearrangement reaction, then it is 4.5 or so to add hydrochloric acid to be adjusted to pH, and point liquid washing distills to reclaim
Dichloromethane, then blowing, suction filtration obtain crude product sulphur humulone；In suction filtration is gone out crude product sulphur humulone input refining reaction kettle while hot,
Stirred 20 minutes at 50 DEG C, suction filtration after blowing, mother liquor enters the distillation of methyl alcohol distillation still and refines to reclaim methyl alcohol, and solid product is passed through
Mesotrione finished product is obtained after dry, air-flow crushing.
The mesotrione product purity for obtaining is 95.77%, and yield is 88.03%.
Embodiment 2
After in 98% concentrated sulfuric acid 1500kg of nitration reaction kettle addition, to methylsulfonyltoluene 350kg and water 300kg, in 5 hours
Uniform 98% nitric acid that 210kg is added dropwise carries out nitration reaction, and 70 minutes are incubated after completion of dropping, obtains nitrification liquid；
7.5kg catalyst V2O5 and 17kg granularities are added in 1~10 micron of nitrogen after nitrification liquid is imported into oxidizing reactor
Change boron powder, it is uniform in 22 hours that 68% nitric acid 890kg is added dropwise after being warming up to 142 degree, while controlling reaction temperature is 146
Degree；50% nitric acid of 350kg was uniformly added dropwise in 15.5 hours again, while controlling reaction temperature is 144 degree；Protected after completion of dropwise addition
Temperature 1 hour.After reaction solution is cooled into 100 degree, 50 degree are cooled to again after adding water 1000kg, then press filtration obtains oxidation product
Thing, rinsing oxidation product is circulated with water 1100kg；To adding NaOH solution to adjust pH value to 9.0 in oxidation product, to dissolve oxidation
Product, it is 60 DEG C that temperature is controlled in adition process；Then blowing centrifugation while hot, is added dropwise hydrochloric acid and adjusts pH value to 2, in temperature 60 C
It is lower to be kept for 30 minutes, it is centrifuged after being cooled to 35 DEG C, is rinsed, obtain final product refined 2- nitro -4- methyl sulfonylbenzoic acids；Refine for five times
It is dried at 55 DEG C afterwards；Thionyl chloride is added in acyl chloride reaction kettle, then puts into 2- nitro -4- mesyl benzene first
, to carry out temperature rising reflux reaction, separated goes out thionyl chloride after reacting 3~4 hours, that is, obtain 2- nitro -4- first sulphurs for acid, DMF
Acyl group chlorobenzoyl chloride.
Condensation is reset：After the 2- nitro -4- methylsulphonyl benzoyl chloride dichloromethane that will be obtained dissolves well, it is cooled to
40 DEG C, the 1 of input 250kg, hydroresorcinol, the uniform 100kg triethylamines that are added dropwise carry out esterification condensation in 80 minutes；Add
230kg acetone cyanohydrins, 110kg triethylamines are added dropwise carries out rearrangement reaction, then it is 5.0 or so to add hydrochloric acid to be adjusted to pH, and point liquid washing is steamed
Evaporate to reclaim dichloromethane, then blowing, suction filtration obtain crude product sulphur humulone；Suction filtration is gone out crude product sulphur humulone input while hot is refined anti-
Answer in kettle, stirred 40 minutes at 55 DEG C, suction filtration after blowing, mother liquor enters the distillation of methyl alcohol distillation still and refines to reclaim methyl alcohol, will be solid
Body product obtains mesotrione finished product after drying, air-flow crushing.
The mesotrione product purity for obtaining is 93.01%, and yield is 88.50%.
Embodiment 3
After in 98% concentrated sulfuric acid 1450kg of nitration reaction kettle addition, to methylsulfonyltoluene 355kg and water 315kg, 4.5 hours
98% nitric acid of interior uniform dropwise addition 205kg carries out nitration reaction, and 65 minutes are incubated after completion of dropping, obtains nitrification liquid；
7.2kg catalyst V2O5 and 15kg granularities are added in 1~10 micron of nitrogen after nitrification liquid is imported into oxidizing reactor
Change boron powder, it is uniform in 21 hours that 68% nitric acid 900kg is added dropwise after being warming up to 142 degree, while controlling reaction temperature is 145
Degree；50% nitric acid of 350~370kg was uniformly added dropwise in 16 hours again, while controlling reaction temperature is 143 degree；Completion of dropwise addition
It is incubated 1.5 hours afterwards.After reaction solution is cooled into 100 degree, 49 degree are cooled to again after adding water 900kg, then press filtration obtains oxygen
Change product, rinsing oxidation product is circulated with water 1050kg；To adding NaOH solution to adjust pH value to 8.5 in oxidation product, to dissolve
Oxidation product, it is 57 DEG C that temperature is controlled in adition process；Then blowing centrifugation while hot, is added dropwise hydrochloric acid and adjusts pH value to 1.5, in temperature
Kept for 40 minutes in the range of 57 DEG C of degree, be centrifuged after being cooled to 35 DEG C, rinsed, obtain final product refined 2- nitro -4- mesyl benzene first
Acid, four times it is refined after it is dried at 65 DEG C；Thionyl chloride is added in acyl chloride reaction kettle, then puts into 2- nitro -4- first
, to carry out temperature rising reflux reaction, separated goes out thionyl chloride after reacting 3~4 hours, that is, obtain 2- for sulfonyl benzoic acid, DMF
Nitro -4- methylsulphonyl benzoyl chlorides.
After the 2- nitro -4- methylsulphonyl benzoyl chloride dichloromethane that will be obtained dissolves well, 37 DEG C, input are cooled to
The 1 of 245kg, hydroresorcinol, the uniform 95kg triethylamines that are added dropwise carry out esterification condensation in 70 minutes；Add 220kg acetone
Cyanalcohol, dropwise addition 105kg triethylamines carry out rearrangement reaction, then it is 4.8 or so to add hydrochloric acid to be adjusted to pH, and point liquid washing distills to reclaim
Dichloromethane, then blowing, suction filtration obtain crude product sulphur humulone；In suction filtration is gone out crude product sulphur humulone input refining reaction kettle while hot,
Stirred 30 minutes at 53 DEG C, suction filtration after blowing, mother liquor enters the distillation of methyl alcohol distillation still and refines to reclaim methyl alcohol, and solid product is passed through
Mesotrione finished product is obtained after dry, air-flow crushing.
The mesotrione product purity for obtaining is 95.44%, and yield is 89.17%.
Finally it should be noted that：Various embodiments above is merely illustrative of the technical solution of the present invention, rather than its limitations；To the greatest extent
Pipe has been described in detail with reference to foregoing embodiments to the present invention, it will be understood by those within the art that：Its according to
The technical scheme described in foregoing embodiments can so be modified, or which part or all technical characteristic are entered
Row equivalent；And these modifications or replacement, the essence of appropriate technical solution is departed from various embodiments of the present invention technology
The scope of scheme.
Claims (4)
1. a kind of synthesis technique of mesotrione, it is characterised in that including step：
Nitrification：Nitration reaction kettle add the concentrated sulfuric acid 1400~1500kg, to 350~360kg of methylsulfonyltoluene and water 300~
After 330kg, the uniform nitric acid that 200~210kg is added dropwise carries out nitration reaction in 4~5 hours, and 60~70 points are incubated after completion of dropping
Clock, obtains nitrification liquid；
Oxidation：Nitrification liquid is imported 1~10 micron that catalyst V2O5 and 15~20kg are added after oxidizing reactor of nitridation
Boron powder, then 1240~1290kg nitric acid is added dropwise, and controlling reaction temperature is 142~146 DEG C；1-2 is incubated after completion of dropwise addition small
When；After reaction solution is cooled into 100 degree, 48~50 degree are cooled to again after adding water 800~1000kg, then press filtration is aoxidized
Product, rinsing oxidation product is circulated with 1000~1100kg of water；It is done at 55~70 DEG C after oxidation product is repeatedly refined
It is dry to obtain 2- nitro -4- methyl sulfonylbenzoic acids；
Chloride：Thionyl chloride is added in acyl chloride reaction kettle, then puts into 2- nitro -4- methyl sulfonylbenzoic acids, DMF to enter
Row temperature rising reflux reacts, and separated goes out thionyl chloride after reacting 3~4 hours, obtains 2- nitro -4- methylsulphonylbenzoyls
Chlorine, and；
Condensation is reset：2- nitro -4- methylsulphonyl benzoyl chloride the dichloromethane that will be obtained dissolve it is good after, be cooled to 35~
40 DEG C, the 1 of 240~250kg of input, hydroresorcinol, uniform 90~100kg triethylamines that are added dropwise carry out ester in 60~80 minutes
Change condensation；210~230kg acetone cyanohydrins are added, 100~110kg triethylamines are added dropwise carries out rearrangement reaction, then adds hydrochloric acid to be adjusted to
PH is 4.5~5.0, point liquid washing, is distilled to reclaim dichloromethane, and then blowing, suction filtration obtain crude product sulphur humulone；While hot by suction filtration
In the crude product sulphur humulone input refining reaction kettle for going out, stirred 20~40 minutes at 50~55 DEG C, suction filtration after blowing, mother liquor enters first
The distillation of alcohol distillation still is refined to reclaim methyl alcohol, and solid product is obtained into mesotrione finished product after drying, air-flow crushing.
2. synthesis technique as claimed in claim 1, it is characterised in that in the oxidation step, the consumption of catalyst V2O5
It is 7~7.5kg.
3. synthesis technique as claimed in claim 2, it is characterised in that in the oxidation step, when nitric acid is added dropwise, exists first
It is uniform in 20~22 hours that 890~920kg of nitric acid is added dropwise, while controlling reaction temperature is 144~146 degree；Again 15.5~17
It is uniform in hour that 350~370kg nitric acid is added dropwise, while controlling reaction temperature is 142-144 degree；Insulation 1~2 is small after completion of dropwise addition
When.
4. synthesis technique as claimed in claim 3, it is characterised in that when the oxidation product is refined, in oxidation product
NaOH solution is added to adjust pH value to 8.0~9.0, to dissolve oxidation product, it is 55~60 DEG C that temperature is controlled in adition process；So
Blowing centrifugation while hot afterwards, is added dropwise hydrochloric acid and adjusts pH value to 1~2, is kept for 30~50 minutes in the range of 55~60 DEG C of temperature, is cooled to
It is centrifuged after 35 DEG C, rinsed, obtains final product refined 2- nitro -4- methyl sulfonylbenzoic acids.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610994931.7A CN106748919A (en) | 2016-11-11 | 2016-11-11 | A kind of synthesis technique of mesotrione |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610994931.7A CN106748919A (en) | 2016-11-11 | 2016-11-11 | A kind of synthesis technique of mesotrione |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN106748919A true CN106748919A (en) | 2017-05-31 |
Family
ID=58973123
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610994931.7A Pending CN106748919A (en) | 2016-11-11 | 2016-11-11 | A kind of synthesis technique of mesotrione |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106748919A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113354563A (en) * | 2021-06-07 | 2021-09-07 | 浙江天诺医药科技有限公司 | Method for preparing triketone compound by continuous flow |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4780127A (en) * | 1982-03-25 | 1988-10-25 | Stauffer Chemical Company | Certain 2-(substituted benzoyl)-1,3-cyclohexanediones and their use as herbicides |
| CN1347342A (en) * | 1999-04-15 | 2002-05-01 | 纳幕尔杜邦公司 | Vanadyl pyrophosphate oxidation catalyst |
| CN1116266C (en) * | 1997-11-27 | 2003-07-30 | 曾尼卡有限公司 | Process for preparation of acylated cyclic 1,3-dicarbonyl compounds |
| CN1543455A (en) * | 2001-08-17 | 2004-11-03 | 三共农业株式会社 | 3-phenoxy-4-pyridazinol derivative and herbicide composition containing the same |
| CN101594934A (en) * | 2007-01-19 | 2009-12-02 | 巴斯夫欧洲公司 | The preparation active compound is the method for the molded catalyst bodies of multielement oxide |
| CN101632925A (en) * | 2008-06-19 | 2010-01-27 | 三菱瓦斯化学株式会社 | Catalyst and method for producing carboxylic acid and/or carboxylic anhydride in the presence of the catalyst |
| CN101987911A (en) * | 2009-08-07 | 2011-03-23 | 骏马化纤股份有限公司 | Method for increasing crystallization rate of poly(ethylene 2, 6-naphthalate) |
| GB2530838A (en) * | 2015-06-08 | 2016-04-06 | Rotam Agrochem Int Co Ltd | Process for preparing mesotrione |
-
2016
- 2016-11-11 CN CN201610994931.7A patent/CN106748919A/en active Pending
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4780127A (en) * | 1982-03-25 | 1988-10-25 | Stauffer Chemical Company | Certain 2-(substituted benzoyl)-1,3-cyclohexanediones and their use as herbicides |
| CN1116266C (en) * | 1997-11-27 | 2003-07-30 | 曾尼卡有限公司 | Process for preparation of acylated cyclic 1,3-dicarbonyl compounds |
| CN1347342A (en) * | 1999-04-15 | 2002-05-01 | 纳幕尔杜邦公司 | Vanadyl pyrophosphate oxidation catalyst |
| CN1543455A (en) * | 2001-08-17 | 2004-11-03 | 三共农业株式会社 | 3-phenoxy-4-pyridazinol derivative and herbicide composition containing the same |
| CN101594934A (en) * | 2007-01-19 | 2009-12-02 | 巴斯夫欧洲公司 | The preparation active compound is the method for the molded catalyst bodies of multielement oxide |
| CN101632925A (en) * | 2008-06-19 | 2010-01-27 | 三菱瓦斯化学株式会社 | Catalyst and method for producing carboxylic acid and/or carboxylic anhydride in the presence of the catalyst |
| CN101987911A (en) * | 2009-08-07 | 2011-03-23 | 骏马化纤股份有限公司 | Method for increasing crystallization rate of poly(ethylene 2, 6-naphthalate) |
| GB2530838A (en) * | 2015-06-08 | 2016-04-06 | Rotam Agrochem Int Co Ltd | Process for preparing mesotrione |
Non-Patent Citations (6)
| Title |
|---|
| 余刚 等: "玉米田除草剂甲基磺草酮的合成", 《江苏农业学报》 * |
| 杨剑波 等: "硝磺酮的合成与除草效果", 《农药》 * |
| 杨静: "新型高效除草剂甲基磺草酮的合成研究", 《山东大学硕士学位论文》 * |
| 游华南 等: "硝磺草酮合成工艺的改进", 《农药》 * |
| 田学芳 等: "新型玉米田除草剂甲基磺草酮的合成研究", 《河北化工》 * |
| 程正载 等: "新型除草剂甲基磺草酮的合成", 《农药》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113354563A (en) * | 2021-06-07 | 2021-09-07 | 浙江天诺医药科技有限公司 | Method for preparing triketone compound by continuous flow |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| WO2015058519A1 (en) | A triketone compound and preparation method and use thereof | |
| EP0212617B1 (en) | Process for producing 4-biphenylylacetic acid | |
| CN106699570B (en) | Synthesis method of (2-chloro-5-iodophenyl) (4-fluorophenyl) ketone | |
| CN113135867B (en) | S- (5, 5-dimethyl-4, 5-dihydroisoxazol-3-yl) ethyl acetate and synthetic method and application thereof | |
| CN106748919A (en) | A kind of synthesis technique of mesotrione | |
| CN106565560A (en) | Synthesis process of mesotrione | |
| CN106565556A (en) | Synthetic process of mesotrione | |
| CN106748918A (en) | A kind of synthesis technique of mesotrione | |
| CN113880846B (en) | Preparation method of 7-iodopyrrolo [2,1-F ] [1,2,4] triazin-4-amine | |
| CN106008385A (en) | Synthesis method of parecoxib sodium | |
| CN106565561A (en) | 2-nitro-4-methylsulfonylbenzoylchloride synthesizing process | |
| CN110294748B (en) | Synthesis method of teneligliptin key intermediate | |
| CN108610290B (en) | Preparation method of fluxapyroxad | |
| CN113277984B (en) | Method for preparing 3, 6-dichloropyridazine-4-alcohol | |
| CN106565557A (en) | Synthesis process of 2-nitro-4-methylsulfonyl benzoyl chloride | |
| CN106565558A (en) | Synthesis process of 2-nitro-4-methanesulfonylbenzoyl chloride | |
| CN109160908A (en) | A kind of synthetic method of 2- methoxy imino -2- furans acetic acid | |
| CN106565562A (en) | Synthesis process of 2-nitro-4-methylsulfonylbenzoic acid | |
| CN106565555A (en) | Synthesis process of 2-nitro-4-methylsulfonylbenzoic acid | |
| US5010192A (en) | Pyridazinone manufacture | |
| CN106565559A (en) | Synthetic process of 2-nitryl-4-methanesulfonyl benzoic acid | |
| US9000180B2 (en) | Processes for the production of N-substituted sulfoximine pyridine N-oxides | |
| CN117069711A (en) | Preparation method of benzoxazine-4-one derivative | |
| CN110283128A (en) | Utilize the method for Methyl cyanocarbamate synthesis mebendazole | |
| US3812156A (en) | Process for preparing lower alkyl flavone-7-oxyacetates |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20170531 |
|
| RJ01 | Rejection of invention patent application after publication |