581809-46-3

Usage

Uses

Used in Agriculture:
Bixafen is used as a fungicide for the control of key stem and leaf diseases in cereal crops. It is effective against strobilurin-resistant septoria, making it a valuable tool in managing crop diseases and ensuring a healthy harvest.
Used in Cereal Crop Protection:
Bixafen is used as a protective agent in cereal crops to prevent and control various stem and leaf diseases. Its effectiveness against strobilurin-resistant septoria makes it a crucial component in integrated pest management strategies for cereal production.

Upstream product

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• 371-40-4 4-fluoroaniline 
• 151733-96-9 ethyl 3-(difluoromethyl)-1H-pyrazole-4-carboxylate 
• 1003-98-1 2-bromo-4-fluoroaniline 
• 151169-75-4 3,4-dichlophenylboronic acid 
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• 2106-50-5 2-chloro-4-fluoro-1-nitrobenzene 
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• 1416964-70-9 C₆H₃Cl₂N₂O^(1-)*Na⁽¹⁺⁾ 
• 95-76-1 m,p-dichloroaniline 
• 141573-95-7 ethyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate 

Relevant academic research and scientific papers

Pd-Catalysed Suzuki-Miyaura cross-coupling of aryl chlorides at low catalyst loadings in water for the synthesis of industrially important fungicides

The Suzuki-Miyaura coupling reaction of electron-poor aryl chlorides in the synthesis of crop protection-relevant active ingredients in water is disclosed. Optimisation of the reaction conditions allowed running the reaction with 50 ppm of Pd-catalyst loading without an additional organic solvent in the cross-coupling reaction step in short reaction times. The system was optimised for the initial cross-coupling step of the large scale produced fungicides Boscalid, Fluxapyroxad and Bixafen up to 97% yield. It is also shown that the Suzuki-Miyaura reaction can be easily scaled up to 50 g using a simple product separation and purification using environmentally benign solvents in the work-up. To show the usability of this method, it was additionally applied in the three-step synthesis of the desired active ingredients.

Synthesis method of bixafen based on Suzuki reaction

The invention discloses a synthesis method of bixafen based on Suzuki reaction. Compared with the prior art, the method has the advantages that high-toxicity, flammable and explosive carbon monoxide gas is avoided, a palladium metal catalyst complicated in preparation is avoided, and the bixafen product is prepared by using a tetra (triphenylphosphine) palladium catalyst which is relatively cheap and easy to obtain through a mild Suzuki reaction with high universality. The method disclosed by the invention has the characteristics of being integrally simple, economical, environment-friendly, safe and efficient, and has relatively high industrial application potential.

PRODUCTION METHOD FOR PYRAZOLE-4-CARBOXAMIDE DERIVATIVE

The present invention relates to a method of producing a pyrazole-4-carboxamide derivative including subjecting a pyrazole-4-carboxylic acid ester and an amine to an aminolysis reaction in a solvent in the presence of a base, provided that the reaction is

PROCESS FOR THE MANUFACTURE OF IMINIUM COMPOUNDS AND THEIR APPLICATION IN THE MANUFACTURE OF PYRAZOLE DERIVATIVES

Process for the manufacture of iminium compounds and their application in the manufacture of pyrazole derivatives The present invention concerns processes for the manufacture of iminium compounds and their application in the manufacture of pyrazole derivatives, in particular in processes for the manufacture of pharmaceutically or agrochemically active compounds.

PROCESS FOR THE MANUFACTURE OF PYRAZOLE CARBOXYLIC DERIVATIVES AND PRECURSORS THEREOF

The present invention concerns processes for the manufacture of pyrazole carboxylic derivatives and precursors thereof.

PROCESS FOR THE MANUFACTURE OF PYRAZOLE COMPOUNDS

Disclosed are processes for the manufacture of pyrazole compounds of formula (I) and their application in the manufacture of pyrazole derivatives, in particular in processes for the manufacture of pharmaceutically or agrochemically active compounds, wherein in the processes, at least two steps are conducted in the presence of at least one solvent which is the same in the at least two steps, wherein the at least one same solvent is selected from the group consisting of aromatic hydrocarbons, alkanes, carboxylic acid esters, ethers, nitriles and dimethylformamide.

Synthesis method of bixafen

The invention relates to a synthesis method of bixafen. The method comprises the steps that firstly, 3,4-dichloroaniline is prepared into 3,4-dichloro phenylhydrazine hydrochloride through a reductionagent, then air is introduced into the 3,4-dichloro phenylhydrazine hydrochloride under an alkaline environment, the 3,4-dichloro phenylhydrazine hydrochloride and para-fluoroaniline are subjected tooxidative coupling for obtaining an intermediate 3',4'-dichloro-5-fluorine-2-benzidine, and finally the intermediate and 1-methyl-3-difluoro methyl-4-parazole formyl chloride are subjected to an amidation reaction for preparing the bixafen. According to the adopted technology, the reaction conditions are mild and easy to control, operation is easily and conveniently conducted, the product is easyto purify, and the product can be obtained directly through recrystallization. The control method for intermediates in all steps is simple and accurate, the product yield is high, the atom economy isgood, complex aftertreatment of an old method is avoided, and the method has great competitive advantages and high industry production utilization value. Meanwhile, application of raw materials, withhigh dangerousness, such as butyllithium is avoided, generation of a large amount of solid waste of tarry substances is avoided, the content of the three wastes is extremely low, and the method accords with the concept of environment-friendly chemistry.

METHOD FOR THE PREPARATION OF 3-FLUOROALKYL-1-METHYLPYRAZOL-4-CARBOXYLIC ACID

The present invention relates to method for the preparation of 3-fluoroalkyl-1-methylpyrazol-4-carboxylic acid, wherein it comprises the following steps: step 1, fluoroacetyl fluoride derivative shown in Formula I undergoes condensation with dimethylamino vinyl methyl ketone, as a result, 3-dimethylamino methylene-fluoro-2,4-pentanedione derivative shown in Formula II is formed; step 2, ring closing reaction takes place between said 3-dimethylamino methylene-fluoro-2,4-pentanedione shown in Formula II and methylhydrazine, in this way, 3-fluoroalkyl-1-methyl-4-acetyl pyrazol derivative shown in Formula III is obtained; step 3, the said 3-fluoroalkyl-1-methyl-4-acetyl pyrazol derivative shown in Formula III is oxidized in the presence of alkali, and then acidified, in this way, 3-fluoroalkyl-1-methylpyrazol-4-carboxylic acid shown in Formula IV is formed. Preparing method of present invention, wherein the required preparing route is simple, the raw material cost is low, the resulting yield of each step is high, and it is suitable for industrialization.

Synthesis of Celecoxib, Mavacoxib, SC-560, Fluxapyroxad, and Bixafen Enabled by Continuous Flow Reaction Modules

Multi-step continuous flow synthesis enables a parallel approach to obtain agrochemicals and pharmaceuticals containing 3-fluoroalkyl pyrazole cores. In this system, fluorinated amines are transformed into pyrazole cores through a telescoped in situ generation and consumption of diazoalkanes. Once synthesized, additional continuous flow and batch reactions add complexity to the pyrazole core via C–N arylation and methylation, TMS cleavage, and amidation. Using this modular assembly line approach, Bixafen and Fluxapyroxad were synthesized in 38 % yield over four continuous flow steps in an overall reaction time of 56 min. Finally, coupling selected continuous flow processes with an offline (batch) Ullmann coupling afforded Celecoxib, Mavacoxib, and SC-560 in 33–54 % yield over two to three steps.

PROCESS FOR THE MANUFACTURE OF CARBOXAMIDES

The present invention concerns a process for the manufacture of carboxamides, in particular agrochemical or pharmaceutically active ingredients, from pyrazole ketone compounds.