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

Description

Hymexazol, a member of the isoxazoles class, is a chemical compound characterized by hydroxy and methyl substituents at positions 3 and 5, respectively. It is a white solid that is widely used as a systemic soil and seed fungicide. Hymexazol is known for its effectiveness in controlling soil-borne diseases and promoting plant growth.

Uses

Used in Pesticide Industry:
Hymexazol is used as a pesticide for controlling soil-borne diseases caused by various pathogens such as Fusarium, Aphanomyces, Pythium, Corficium, and Typhula spp. It is effective in a range of crops, including rice, sugar beet, fodder beet, vegetables, cucurbits, ornamentals, carnations, and forest tree seedlings.
Used in Agricultural Fungicide Industry:
As an agricultural fungicide, Hymexazol plays a crucial role in protecting crops from soil-borne diseases, ensuring a healthy growth environment and increased yield.
Used in Plant Growth Regulation:
Hymexazol also serves as a plant growth regulator, stimulating some aspects of plant growth and contributing to overall crop health and productivity.
Used in Seed Dressing:
In addition to its fungicidal properties, Hymexazol is utilized as a seed dressing, providing protection for seeds against soil-borne diseases and promoting a strong start for the growing plants.

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

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

Downstream Products

• 24827-14-3 3-benzoyloxy-5-methyl-isoxazole 
• 118938-22-0 5-methyl-2-(4-ethoxycarbonyl-2-nitrophenyl)-4-isoxazolin-3-one 
• 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 
• 16864-45-2 3-methoxy-5-methylisoxazole 
• 27066-53-1 5-methylisoxazol-3-yl dimethylcarbamate 
• 115886-00-5 3-(benzyloxy)-5-methyl-1,2-oxazole 
• 1260599-37-8 5-methyl-3-(4-formylphenoxy)isoxazole 
• 1240402-52-1 5-Methyl-4-(5-methyl-isoxazol-3-yloxymethyl)-3-phenyl-isoxazole 
• 1153949-81-5 1-(4-(2-chloropyrimidin-4-yl)-1H-pyrazol-1-yl)-4-((5-methylisoxazol-3-yl)oxy)cyclohexylacetonitrile 
• 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 
• 596809-68-6 5-methyl-3-isoxazolyl benzenesulfonate 
• 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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Photoactivatable AMPA for the study of glutamatergic neuronal transmission using two-photon excitation

We report a photoactivatable agonist of the AMPA subtype of ionotropic glutamate receptors, TMP-CyHQ-AMPA, which was designed to study the fast excitatory transmission between neurons. Upon visible light excitation, TMP-CyHQ-AMPA quantitatively released AMPA in high quantum yield on an ultra-short timescale. Intriguingly, the photolyisis can be carried out using 2-photon excitation (2PE) with remarkable efficiency, giving a two-photon uncaging action cross section (δu) value of 1.71 GM. TMP-CyHQ-AMPA is soluble in pysiological buffer and no hydrolysis was detected in the absence of light. Molecular docking experiments indicated that the photocaging strategy abolishes the affinity of AMPA for the GluR2 receptor and no GABAergic effects (as commonly observed in caged glutamates) are expected. TMP-CyHQ-AMPA can be used to study glutamatergic neuronal transmission with exceptional spatial-temporal resolution in complex tissue preparations.

Hymexazol synthesis method

The invention relates to the field of pesticides, and specifically discloses a synthesis method of hymexazol. According to the method, a sodium carbonate-sodium bicarbonate system is adopted to carry out reactions, methyl (ethyl) acetoacetate and hydroxylamine hydrochloride are taken as the raw materials; by dropwise adding sodium hydroxide and methyl (ethyl) acetoacetate, the pH of the condensation reaction system is controlled, through the reaction system, the pH can be stably controlled, after the condensation reactions, the condensation reaction products are slowly dropwise added into preheated concentrated hydrochloric acid to carry out ring-closure reactions; the provided method can obviously reduce the generation of impurities, the yield of hymexazol is increased to 70% or above, and moreover, the synthesis method is environment-friendly and is suitable for industrial production.