447399-55-5

Usage

Uses

Used in Pharmaceutical Industry:
3-([5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methylsulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole is used as a potential pharmaceutical agent for its possible biological activity. The presence of multiple functional groups may allow it to interact with biological targets, making it a candidate for the development of new drugs.
Used in Agrochemical Industry:
In the agrochemical sector, 3-([5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methylsulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole may be utilized as a component in the development of new pesticides or herbicides. Its complex structure and potential reactivity could offer novel modes of action against pests and weeds.
Used in Materials Science:
3-([5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methylsulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole could be employed in materials science for the creation of new materials with unique properties. Its structural features may contribute to the development of advanced materials with applications in various industries, such as electronics, coatings, or adhesives.
Further research and analysis are essential to understand the full potential of 3-([5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methylsulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole and to explore its applications across different industries.

Synthetic route

3-(((5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl)methyl)thio)-5,5-dimethyl-4,5-dihydroisoxazole (656825-92-2) → pyroxasulfone (447399-55-5)

Conditions	Yield
With sodium tungstate (VI) dihydrate; sulfuric acid; dihydrogen peroxide In methanol at 25℃; for 5h; Reagent/catalyst;	95%
With 3-chloro-benzenecarboperoxoic acid In chloroform at 0 - 20℃; for 4h;	86%
With 3-chloro-benzenecarboperoxoic acid In chloroform at 0 - 20℃;	80.6%

2-methyl-5-trifluoromethyl-2H-pyrazol-3-ol (122431-37-2) → pyroxasulfone (447399-55-5)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydroxide / water / 2.58 h / 24 °C 1.2: 16 h / 20 °C 1.3: 16 h / 14 - 20 °C 2.1: sodium hydroxide / acetonitrile / 1.67 h / 20 - 24 °C 2.2: 60.75 h / 5 - 20 °C 3.1: dihydrogen peroxide / sodium tungstate (VI) dihydrate / acetic acid / 16.33 h / 20 - 34 °C View Scheme
Multi-step reaction with 3 steps 1.1: sodium hydroxide; formaldehyd / water / 1.5 h / 25 °C 1.2: 5.33 h / 25 °C 2.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 25 °C 2.2: 6 h / 25 °C 3.1: sodium tungstate (VI) dihydrate; sulfuric acid; dihydrogen peroxide / methanol / 5 h / 25 °C View Scheme
Multi-step reaction with 4 steps 1: sodium hydroxide / water; acetonitrile 2: thionyl chloride / 1,2-dichloro-ethane / 0.5 h / 0 - 25 °C 3: potassium carbonate / acetonitrile / 4 h 4: sodium tungstate (VI) dihydrate; sulfuric acid; dihydrogen peroxide / methanol / 6 h View Scheme
Multi-step reaction with 5 steps 1: potassium hydroxide; formaldehyd / water / 40 °C 2: potassium hydroxide; water / acetonitrile / 25 °C 3: thionyl chloride / acetonitrile / 20 °C 4: sodium hydroxide / water / 100 °C 5: sodium tungstate; dihydrogen peroxide / 100 °C View Scheme

[5,5-dimethyl(4,5-dihydroisoxazol-3-yl)]thiocarboxamidine hydrochloride → pyroxasulfone (447399-55-5)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydroxide / water / 2.58 h / 24 °C 1.2: 16 h / 20 °C 1.3: 16 h / 14 - 20 °C 2.1: sodium hydroxide / acetonitrile / 1.67 h / 20 - 24 °C 2.2: 60.75 h / 5 - 20 °C 3.1: dihydrogen peroxide / sodium tungstate (VI) dihydrate / acetic acid / 16.33 h / 20 - 34 °C View Scheme
Multi-step reaction with 3 steps 1.1: sodium hydroxide; formaldehyd / water / 1.5 h / 25 °C 1.2: 5.33 h / 25 °C 2.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 25 °C 2.2: 6 h / 25 °C 3.1: sodium tungstate (VI) dihydrate; sulfuric acid; dihydrogen peroxide / methanol / 5 h / 25 °C View Scheme

Methyl 3,3-dimethylacrylate (924-50-5) → pyroxasulfone (447399-55-5)

Conditions

Yield

Multi-step reaction with 6 steps 1.1: N-hydroxyurea; potassium methanolate / methanol / 18.5 h / 25 °C / Inert atmosphere 2.1: phosphorus pentachloride / 1,2-dichloro-ethane / 5 h / 25 °C / Inert atmosphere 3.1: hydrogenchloride / tert-butyl alcohol; water / 10.5 h / 25 °C 4.1: sodium hydroxide; formaldehyd / water / 1.5 h / 25 °C 4.2: 5.33 h / 25 °C 5.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 25 °C 5.2: 6 h / 25 °C 6.1: sodium tungstate (VI) dihydrate; sulfuric acid; dihydrogen peroxide / methanol / 5 h / 25 °C View Scheme

5,5-dimethyl-3-isoxazolidinone (62243-00-9) → pyroxasulfone (447399-55-5)

Conditions

Yield

Multi-step reaction with 5 steps 1.1: phosphorus pentachloride / 1,2-dichloro-ethane / 5 h / 25 °C / Inert atmosphere 2.1: hydrogenchloride / tert-butyl alcohol; water / 10.5 h / 25 °C 3.1: sodium hydroxide; formaldehyd / water / 1.5 h / 25 °C 3.2: 5.33 h / 25 °C 4.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 25 °C 4.2: 6 h / 25 °C 5.1: sodium tungstate (VI) dihydrate; sulfuric acid; dihydrogen peroxide / methanol / 5 h / 25 °C View Scheme

3-chloro-5,5-dimethyl-4,5-dihydroisoxazoline (326829-08-7) → pyroxasulfone (447399-55-5)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: hydrogenchloride / tert-butyl alcohol; water / 10.5 h / 25 °C 2.1: sodium hydroxide; formaldehyd / water / 1.5 h / 25 °C 2.2: 5.33 h / 25 °C 3.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 25 °C 3.2: 6 h / 25 °C 4.1: sodium tungstate (VI) dihydrate; sulfuric acid; dihydrogen peroxide / methanol / 5 h / 25 °C View Scheme
Multi-step reaction with 3 steps 1: hydrogen bromide / isobutene / 25 - 40 °C 2: sodium hydroxide / water / 100 °C 3: sodium tungstate; dihydrogen peroxide / 100 °C View Scheme

(5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)- 1H-pyrazol-4-yl)methanol (946409-52-5) → pyroxasulfone (447399-55-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: thionyl chloride / 1,2-dichloro-ethane / 0.5 h / 0 - 25 °C 2: potassium carbonate / acetonitrile / 4 h 3: sodium tungstate (VI) dihydrate; sulfuric acid; dihydrogen peroxide / methanol / 6 h View Scheme
Multi-step reaction with 3 steps 1: thionyl chloride / acetonitrile / 20 °C 2: sodium hydroxide / water / 100 °C 3: sodium tungstate; dihydrogen peroxide / 100 °C View Scheme

3-bromo-5,5-dimethyl-4,5-dihydroisoxazole (882697-80-5) → pyroxasulfone (447399-55-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrogen bromide / tert-butyl alcohol 2: potassium carbonate / acetonitrile / 4 h 3: sodium tungstate (VI) dihydrate; sulfuric acid; dihydrogen peroxide / methanol / 6 h View Scheme

4-(chloromethyl)-5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)-1H-pyrazole + 5,5-dimethyl-4,5-dihydroisoxazol-3-yl carbamimidothioate hydrobromide → pyroxasulfone (447399-55-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / acetonitrile / 4 h 2: sodium tungstate (VI) dihydrate; sulfuric acid; dihydrogen peroxide / methanol / 6 h View Scheme

3-[[[5-(hydroxy)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl]thio]-4,5-dihydro-5,5-dimethylisoxazole (447402-29-1) + Chlorodifluoromethane (75-45-6) → pyroxasulfone (447399-55-5)

Conditions	Yield
Stage #1: 3-[(5-hydroxy-1-methyl-3-trifluoromethylpyrazol-4-yl)-methylthio]-4,5-dihydro-5,5-dimethylisooxazole; Chlorodifluoromethane With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 6h; Stage #2: With sodium tungstate (VI) dihydrate; sulfuric acid; dihydrogen peroxide In methanol for 6h;

potassium 4-(hydroxymethyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-olate → pyroxasulfone (447399-55-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: potassium hydroxide; water / acetonitrile / 25 °C 2: thionyl chloride / acetonitrile / 20 °C 3: sodium hydroxide / water / 100 °C 4: sodium tungstate; dihydrogen peroxide / 100 °C View Scheme

pyroxasulfone (447399-55-5) + GLUTATHIONE (70-18-8) → C15H24N4O7S

Conditions	Yield
With TaQ8GTC1-R protein In aq. phosphate buffer; glycerol at 30℃; for 1h; pH=6.8;

Upstream product

• 656825-92-2 3-(((5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl)methyl)thio)-5,5-dimethyl-4,5-dihydroisoxazole 
• 122431-37-2 2-methyl-5-trifluoromethyl-2H-pyrazol-3-ol 
• 924-50-5 Methyl 3,3-dimethylacrylate 
• 62243-00-9 5,5-dimethyl-3-isoxazolidinone 
• 326829-08-7 3-chloro-5,5-dimethyl-4,5-dihydroxyisoxazole 
• 946409-52-5 (5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)- 1H-pyrazol-4-yl)methanol 
• 882697-80-5 3-bromo-5,5-dimethyl-4,5-dihydroisoxazole 
• 447402-29-1 3-[[[5-(hydroxy)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl]thio]-4,5-dihydro-5,5-dimethylisoxazole 
• 75-45-6 Chlorodifluoromethane 

Relevant academic research and scientific papers

Synthesis method of sulfolazamide

The present invention discloses a method of synthesis of sulfolapriazole, 1-methyl-3-trifluoromethyl-5-hydroxy-1H-pyrazole as raw material, in the presence of an organic solvent and lye, hydroxymethylation reaction with formaldehyde to give hydroxypyrazole methanol; hydroxypyrazole methanol and difluorochloromethane for etherification reaction to give etherified pyrazole methanol; and then etherified pyrazol methanol and isoxazole urea salt and phase transfer catalyst for condensation reaction to obtain sulfur ether; the sulfur ether and hydrogen peroxide in the presence of the catalyst oxidation reaction, Get piroxazole sulfoxide. The technical route of sulfolarazole designed of the present invention is different from the existing process route, its reaction steps are short, the yield is high, the cost is low, and the hydroxymethylation, etherification and condensation reaction can be directly carried out in the same reaction flask directly in a pot reaction, more suitable for industrial production.

S-(5, 5-dimethyl-4, 5-dihydroisoxazole-3-yl) ethyl sulfate as well as synthesis method and application of S-(5, 5-dimethyl-4, 5-dihydroisoxazole-3-yl) ethyl sulfate

The invention discloses S-(5, 5-dimethyl-4, 5-dihydroisoxazole-3-yl) ethyl sulfate as well as a synthesis method and application of the S-(5, 5-dimethyl-4, 5-dihydroisoxazole-3-yl) ethyl sulfate. According to the preparation method, 3-halogenated-5, 5-dimethyl-4, 5-dihydroisoxazole reacts with potassium thioacetate to prepare S-(5, 5-dimethyl-4, 5-dihydroisoxazole-3-yl) ethyl sulfate. According to the method, the synthesis process is simplified, the reaction speed is high, the product purity is high, the yield is high, the reaction condition is mild, the equipment cost is low, the synthesis process and the post-treatment process are extensive, the product is easy to separate, the obtained product can be used as a pyroxasulfone intermediate, and a plurality of defects of the 5, 5-dimethyl-4, 5-dihydroisoxazole thiamidine hydrochloride intermediate are avoided.

SOLID STATE FORM OF PYROXASULFONE

The present disclosure relates to a solid state form of Pyroxasulfone, processes for preparation thereof and agrochemical compositions thereof.

PROCESS FOR PREPARATION OF PYROXASULFONE

The present invention discloses a process for the preparation of Pyroxasulfone of Formula (I) or salt thereof. Particularly, the present invention discloses an improved process for the preparation of hydroxycarbonimidic dibromide compound of Formula (III) or salt thereof, wherein bromine anion is recycled by using a suitable oxidizing agent. Moreover, the present invention relates to a continuous flow process for preparing of compound of Formula (I) or salt thereof.

Pyroxasulfone synthesis method

The invention provides a pyroxasulfone synthesis method. The method comprises the steps of: adopting a compound I as a starting raw material, carrying out cyclization reaction to synthesize an intermediate II, and carrying out chlorination reaction on the intermediate II under the action of a chlorination reagent to obtain an intermediate III; reacting the intermediate III with thiourea to obtaina hydrochloride intermediate IV, wherein the chlorination reagent is phosphorus pentachloride and/or phosphorus oxychloride; reacting the hydrochloride intermediate IV and a compound VI with formaldehyde to obtain an intermediate VII, carrying out difluoromethoxylation reaction on the intermediate VII to obtain an intermediate VIII, and oxidizing the intermediate VIII with hydrogen peroxide in thepresence of a catalyst to obtain pyroxasulfone IX, wherein the catalyst is sodium tungstate and acid. According to the method, the total yield is increased to 31-38%, the raw materials are simple andeasily available, the reaction process is simple and safe, the yield is high, and the method has certain significance for industrial production.

Synthesis method and application of pyroxasulfone

The invention relates to the technical field of pesticides, and provides a synthesis method of pyroxasulfone, which comprises the steps of: (1) carrying out a hydroxyalkylation reaction, a fluoromethylation reaction and a chlorination reaction on a reaction body (I) to obtain an intermediate 2; and (2) mixing an intermediate 1 and the intermediate 2, adding water to separate out an organic phase to obtain a transition intermediate, and adding a solvent and an oxidizing agent for reaction to obtain pyroxasulfone. The invention further provides application of pyroxasulfone to pesticides. The pyroxasulfone is prepared by the synthesis method. According to the invention, the overall yield of the target product can be increased, the generation of by-products can be reduced, the generation of three wastes is perfectly reduced, and the recycling of the solvent is realized.

Method for Producing 5,5-Disubstituted 4,5-Dihydroisoxazol-3-Thiocarboxamidine Salts

A process for preparing 5,5-disubstituted 4,5-dihydroisoxazole-3-thiocarboxamidine salts of the formula (I), wherein 3-unsubstituted 4,5-dihydroisoxazoles are first reacted with a chlorinating or brominating reagent to give 3-halogenated 4,5-dihydroisoxazoles and the latter then react with thiourea to give the compounds of the formula (I).

Herbicide compositions

A herbicidal composition which comprises i) an isoxazoline derivative represented by the following general formula (I) or its salt and ii) at least one compound selected from the Group A: Formula (I) wherein R1, R2, R3, R4, R5 and R6 are defined in the specification.

PYRAZOLE DERIVATIVES AND PROCESS FOR THE PRODUCTION THEREOF

The present invention provides pyrazole derivatives useful as production intermediates for isoxazoline derivatives having an excellent herbicidal effect and selectivity between crops and weeds as well as processes for producing the same. The pyrazole derivatives or pharmaceutically acceptable salts thereof which are inventive compounds are represented by the general formula [I] or a salt thereof: wherein R1 represents a C1 to C6 alkyl group, R2 represents a C1 to C3 haloalkyl group, R3 represents a hydrogen atom, a C1 to C3 alkyl group which may be substituted with one or more substituents selected from the following substituent group α, or a formyl group, R4 represents a hydrogen atom or a C1 to C3 haloalkyl group, provided that R4 represents a C1 to C3 haloalkyl group in the case that R3 is a hydrogen or a formyl group, and R4 is a hydrogen group or a C1 to C3 haloalkyl group in the case that R3 is a C1 to C3 alkyl group which may be substituted with one or more substituents selected from the following substituent group α.