10004-44-1

Basic information

• Product Name: Hymexazol
• Synonyms: TACHIGALOZE;TACHIGAREN;3-hydroxy-5-methyl-isoxazol;5-Hydroxy-3-methylisoxazole;5-methyl-3(2h)-isoxazolon;5-methyl-3-isoxazolo;bucid;bucide
• CAS NO: 10004-44-1
• Molecular Formula: C₄H₅NO₂
• Molecular Weight: 99.09
• EINECS: 233-000-6
• Product Categories: Oxazoles, Isoxazoles & Benzoxazoles;Oxazole&Isoxazole;Heterocyclic Compounds;FUNGICIDE;Heterocycles;Oxazoles, Isoxazoles & Benzoxazoles;Agro-Products
• Mol File: 10004-44-1.mol
• Article Data: 20

Chemical Properties

• Melting Point: 80°C
• Boiling Point: 185.54°C (rough estimate)
• Flash Point: 173.7 °C
• Appearance: /Powder
• Density: 1.2992 (rough estimate)
• Vapor Pressure: 0.0493mmHg at 25°C
• Refractive Index: 1.4170 (estimate)
• Storage Temp.: −70°C
• Solubility: Soluble in alcohol, acetone, THF, chloroform
• PKA: 5.91 (weak acid)
• Water Solubility: 65,100 mg l-1 (20 °C)
• Sensitive: Light Sensitive
• Merck: 14,4856
• CAS DataBase Reference: Hymexazol(CAS DataBase Reference)
• NIST Chemistry Reference: Hymexazol(10004-44-1)
• EPA Substance Registry System: Hymexazol(10004-44-1)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-41-52/53
• Safety Statements: 26-39-61
• WGK Germany: 3
• RTECS: NY2932000
• Hazardous Substances Data: 10004-44-1(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 10004-44-1 differently. You can refer to the following data:
1. Pesticide.
2. Agricultural fungicide and plant growth regulator.
3. Hymexazol is used to control soil-borne diseases caused by Fusarium, Aphanomyces, Pythium, Corficium and Typhula spp. in rice, sugar beet, fodder beet, vegetables, cucurbits, ornamentals, carnations and forest tree seedlings. It is also used as a seed dressing and stimulates some plant growth.

Definition

ChEBI: A member of the class of isoxazoles carrying hydroxy and methyl substituents at positions 3 and 5 respectively. It is used worldwide as a systemic soil and seed fungicide for the control of diseases caused by Fusarium, Aphanomyces Pythium, and Corticium spp. in rice, sugarbeet, fodderbeet, vegetables, cucurbits, and ornamentals.

Synthesis Reference(s)

The Journal of Organic Chemistry, 48, p. 4307, 1983 DOI: 10.1021/jo00171a030

Metabolic pathway

Degradation of hymexazol in soil gave acetoacetamide and the product of rearrangement, 5-methyl-2(3H)-oxazolone.H owever, in plants the fungicide was principally converted into its O- and N-glucoside conjugates in the roots and shoots. The two main metabolites of hymexazol found in the urine of rats were the O-glucuronide and sulfate conjugates.

Degradation

Hymexazol is stable under alkaline conditions and relatively stable in acidic conditions. It is stable to sunlight and heat (PM). It should be noted that the parent molecule is tautomeric. Hymexazol is highly volatile and will be lost by volatilisation unless it is covered or incorporated into soil. The fungicide was completely biodegraded in natural water at 30 °C in 2 weeks and at 10-13 °C in 2 months (Rebenok and Kolesnikova, 1983). Hymexazol is stable in sunlight but it is readily degraded by ultraviolet light. Photolysis of an aqueous solution of the fungicide at 253.7 nm, using a low pressure Hg lamp, afforded the oxazolinone (2) as the major product and at least two unidentified minor components. The oxazolinone (2) has been found in soil studies as described below and is a product of rearrangement formed via an aziridinone intermediate as shown in Scheme 1 (Nakagawa et al., 1974).

InChI:InChI=1/C4H5NO2/c1-3-2-4(6)5-7-3/h2H,1H3,(H,5,6)

Synthetic route

carboxamido-2 ethoxy-5 methyl-5 isoxazolone-3 (110795-04-5) → 5-methyl-3(2H)isoxazolone (10004-44-1)

Conditions	Yield
With sodium methylate In methanol for 12h; Ambient temperature;

epoxybutene (930-22-3) + 5-methyl-3(2H)isoxazolone (10004-44-1) → 2-((S)-hydroxymethylallyl)-5-methylisoxazol-3-one (1174758-37-2)

Conditions	Yield
Stage #1: 5-methyl-3(2H)isoxazolone With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; tetrabutylammomium bromide; (1R,2R)-(+)-1,2-diaminocyclohexane-N,N’-bis(2-diphenylphosphino-1-naphthoyl) In acetonitrile for 0.166667h; Inert atmosphere; Stage #2: epoxybutene In acetonitrile at 0℃; for 23h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	77%

5-methyl-3(2H)isoxazolone (10004-44-1) + 1-chloroadamantane (935-56-8) → 2-(1-adamantyl)-5-methyl-2,3-dihydroisoxazol-3-one (83610-15-5)

Conditions	Yield
With chloro-trimethyl-silane; triethylamine; aluminium trichloride 1.) Et2O, 5 h, room temp., 2.) CHCl3, room temp., 1 h; Yield given. Multistep reaction;

5-methyl-3(2H)isoxazolone (10004-44-1) + methyl iodide (74-88-4) → 3-methoxy-5-methylisoxazole (16864-45-2)

Conditions	Yield
With silver(l) oxide In N,N-dimethyl-formamide at 20℃;
With silver(l) oxide In N,N-dimethyl-formamide at 20℃; for 2h;

Upstream product

• 141-97-9 ethyl acetoacetate 
• 87318-59-0 N-(trimethylsilyloxy)-N-(trimethylsilyl)acetoacetamide 
• 110795-04-5 carboxamido-2 ethoxy-5 methyl-5 isoxazolone-3 
• 90587-50-1 N-hydroxyacetoacetamide 
• 105-45-3 acetoacetic acid methyl ester 
• 92234-51-0 methyl β-(1-imidazolyl)crotonoate 
• 10004-24-7 Ethyl tetrolate 
• 3075-23-8 S-ethyl acetothioacetate 
• 674-82-8 4-methyleneoxetan-2-one 

Downstream Products

• 596809-68-6 5-methyl-3-isoxazolyl benzenesulfonate 
• 118938-22-0 5-methyl-2-(4-ethoxycarbonyl-2-nitrophenyl)-4-isoxazolin-3-one 
• 1240402-52-1 5-Methyl-4-(5-methyl-isoxazol-3-yloxymethyl)-3-phenyl-isoxazole 
• 16864-45-2 3-methoxy-5-methylisoxazole 
• 115886-00-5 3-(benzyloxy)-5-methyl-1,2-oxazole 
• 27066-53-1 5-methylisoxazol-3-yl dimethylcarbamate 
• 1260599-37-8 5-methyl-3-(4-formylphenoxy)isoxazole 
• 1153949-81-5 1-(4-(2-chloropyrimidin-4-yl)-1H-pyrazol-1-yl)-4-((5-methylisoxazol-3-yl)oxy)cyclohexylacetonitrile 
• 58011-75-9 5-methyl-3-oxo-3H-isoxazole-2-carboxylic acid 4-(2,4-dichloro-benzoyl)-2,5-dimethyl-2H-pyrazol-3-yl ester 
• 118938-23-1 5-methyl-2-(4-trifluoromethyl-2-nitrophenyl)-4-isoxazolin-3-one 
• 280579-73-9 4-Anilino-5-[(5-methylisoxazol-3-yl)oxymethyl]-2-{4-[2-hydroxy-3-(N,N-dimethylamino)propoxy]anilino}pyrimidine 
• 192439-68-2 5-isopentylisoxazol-3-ol 
• 76422-46-3 5-methyl-3-(p-toluenesulphonyloxy)isoxazole 

Relevant articles and documents

A Continuous Flow Process for the Synthesis of Hymexazol

Hymexazol is an efficient and low-toxicity soil fungicide. In this work, a fully continuous flow process for the synthesis of hymexazol has been developed. This process begins with combining ethyl acetoacetate and hydroxylamine hydrochloride to form a hydroxamic acid intermediate. The reaction solution is then quenched with concentrated hydrochloric acid to obtain the final product, hymexazol. Under the optimized process conditions, the total yield of the target product reached 86%. In addition, production was successfully scaled-up to a kilogram scale. The continuous flow method not only greatly decreases the reaction time but also significantly inhibits the side reactions.

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Method for synthesizing 3,5-disubstituted isoxazole compound based on three-component reaction

The invention provides a method for synthesizing a 3,5-disubstituted isoxazole compound based on three-component reaction, which comprises the following steps: mixing aldehyde, olefin and nitrite, and heating to react to generate the 3,5-disubstituted isoxazole compound. According to the scheme, the safety is greatly improved; the adopted raw materials can be commercially purchased and do not need to be prepared in advance, the reaction implementation is easier, and the reaction operation is simpler and more convenient; the application range of substrates is wider, and aliphatic hydrocarbon, aromatic hydrocarbon, condensed ring and other substrates can be suitable for the reaction system; the reaction can be carried out in both an acidic environment and an alkaline environment; the reaction can be carried out under an air condition without inert gas protection.

Production process of hymexazol technical material

The invention provides a production process of hymexazol technical material. The production process comprises the following steps: hydroxylamine hydrochloride addition, catalyst addition, ethyl acetoacetate dropwise addition, reaction and acidification. The production process of hymexazol technical has the beneficial effects that the selectivity of the catalyst is 99.7-99.9%; the purity of the prepared crude product hymexazol is 91-92%; the yield of the hymexazol technical is 94-95%; the purity of the hymexazol technical material through liquid chromatography detection is 99.98-99.99%. According to the production process of the hymexazol technical material, disclosed by the invention, the catalyst is durable to recycle, and when the catalyst is recycled for 30 times, the purity of the prepared crude product hymexazol is 89.7-90%; the selectivity of the catalyst is 98.5%; the yield of the hymexazol technical is 92-92.4%; the purity of the hymexazol technical material through liquid chromatography detection is more than 99.90%.