18826-96-5

Usage

Uses

Used in Pharmaceutical Industry:
4-AMINO-6-METHYL-3-(METHYLSULFANYL)-1,2,4-TRIAZIN-5(4H)-ONE is used as an intermediate in the synthesis of various pharmaceuticals for its antimicrobial and antitumor properties, contributing to the development of new drugs with potential therapeutic benefits.
Used in Agrochemical Industry:
In the agrochemical sector, 4-AMINO-6-METHYL-3-(METHYLSULFANYL)-1,2,4-TRIAZIN-5(4H)-ONE is utilized as a precursor in the production of herbicides and insecticides, due to its potential to control or eliminate unwanted plant and insect species, thereby enhancing crop protection and yield.
Used in Research and Development:
4-AMINO-6-METHYL-3-(METHYLSULFANYL)-1,2,4-TRIAZIN-5(4H)-ONE is also used in research and development as a compound of interest for exploring its biological activities and potential applications in various fields, including the creation of new chemical entities with specific therapeutic or pesticidal properties.

InChI:InChI=1/C5H8N4OS/c1-3-4(10)9(6)5(11-2)8-7-3/h6H2,1-2H3

Upstream product

• 25412-75-3 4-nitrobenzamidine 
• 109107-02-0 C₂₆H₂₆N₁₀O₄S₂ 
• 111981-40-9 C₂₄H₂₀Cl₂N₁₀O₂S₂ 
• 109107-03-1 C₂₆H₂₆N₁₀O₄S₂ 
• 109107-01-9 C₂₄H₂₂N₁₀O₂S₂ 
• 109106-96-9 C₂₄H₂₀Cl₂N₁₀O₂S₂ 
• 109107-03-1 1,3-bis-(3-methoxyphenyl)-2,4-bis-(6-methyl-3-methylthio-5-oxo-4,5-dihydro-1,2,4-triazin-4-ylimino)-1,3-diazetidine 
• 111981-41-0 1,3-bis(4-chlorophenyl)-2,4-bis(6-methyl-3-(methylthio)-5-oxo-4,5-dihydro-1,2,4-triazin-4-ylimino)-1,3-diazetidine 
• 618-39-3 benzamidin 
• 109107-02-0 1,3-bis-(4-methoxyphenyl)-2,4-bis-(6-methyl-3-methylthio-5-oxo-4,5-dihydro-1,2,4-triazin-4-ylimino)-1,3-diazetidine 
• 60-34-4 methylhydrazine 
• 22278-81-5 4-amino-5-oxo-3-thioxo-6-methyl-2,3,4,5-tetrahydro<1,2,4>triazine 
• 74-88-4 methyl iodide 
• 22278-81-5 4-amino-6-methyl-3-thio-1,2,4-triazin-5-one 

Downstream Products

• 94350-96-6 Pyridiniumsalz d.2-Mercapto-7-oxo-6-methyl-7H-<1.3.4>-thiadiazolo<2.3-c>-as-triazin 
• 77117-19-2 3-p-Tolylamino-4-amino-5-oxo-6-methyl-4,5-dihydro-1,2,4-triazine 
• 109107-00-8 6-Methyl-3-(methylthio)-4-<(triphenylphosphoranylidene)amino>-5-oxo-4,5-dihydro-1,2,4-triazine 
• 96546-30-4 8-phenyl-7-phenylamino-3-methyl<1,2,4>triazolo<5,1-c><1,2,4>triazin-4(8H)-one 
• 89124-32-3 4-amino-3-hydrazino-6-methyl-5-oxo-4,5-dihydro-1,2,4-triazine 
• 88023-93-2 N-(3-methyl-4-oxo-4H-[1,3,4]thiadiazolo[2,3-c][1,2,4]triazin-7-yl)benzamide 
• 109107-01-9 1,3-diphenyl-2,4-bis-(6-methyl-3-methylthio-5-oxo-4,5-dihydro-1,2,4-triazin-4-ylimino)-1,3-diazetidine 
• 109106-96-9 1,3-bis-(4-chlorophenyl)-2,4-bis-(6-methyl-3-methylthio-5-oxo-4,5-dihydro-1,2,4-triazin-4-ylimino)-1,3-diazetidine 
• 109107-02-0 1,3-bis-(4-methoxyphenyl)-2,4-bis-(6-methyl-3-methylthio-5-oxo-4,5-dihydro-1,2,4-triazin-4-ylimino)-1,3-diazetidine 
• 109107-03-1 1,3-bis-(3-methoxyphenyl)-2,4-bis-(6-methyl-3-methylthio-5-oxo-4,5-dihydro-1,2,4-triazin-4-ylimino)-1,3-diazetidine 

Relevant academic research and scientific papers

Facile synthesis of [1,2,4]triazino[4,3-b][1,2,4,5]tetrazepin derivatives by a one-pot reactions using 4-amino-3-hydrazinyl-6-methyl-1,2,4-triazin-5(4H)-one

4-Amino-3-mercapto-6-methyl-1,2,4-triazin-5(4. H)-one 1 converted to 4-amino-6-methy-3-(methylthio)-1,2,4-triazin-5(4. H)-one by methylation with methyl iodide. Controlled hydrazination of the resulting compound afforded 4-amino-3-hydrazinyl-6-methyl-1,2,4-triazin-5(4. H)-one 2 as a building block, to the synthesis of some novel derivatives of [1,2,4]triazino [4,3,. b][1,2,4,5]tetrazepine 3-6, by the reaction with 3-chloropentane-2,4-dione, chloro acetonitrile, 1,3-dichloroacetone, and methyl bromoacetate. This general synthetic procedure can be extended to the preparation of wide variety of tetrazepines using 1,2-bielectrophiles derivatives.

Synthesis, characterization, and biological activity of some aza-uracil derivatives

Thiation of 1 by LR gave the corresponding 3,5-dithioxo derivative 2 and the trimer 3. Methylation of 1 afforded the S-methyl derivative 4. Compound 1 was fused with 6-bromo-2-phenyl-benzo[1,3-d]oxazin-4-one (5) and gave 6. Condensation of 1 with some acid derivatives 7a-d and/or 8a-c yielded thiadiazolo-triazine derivatives 9a-d and 10a-c. Compounds 9a,c and 10c were hydrolyzed to furnish 11a-c. Acetylation of 14 afforded mono- and diacetyl-derivatives 15 and 16. Benzoylation of 14 afforded mono- and dibezoyl-derivatives 17 and 18. 14 with some aromatic aldehydes yielded 19a-c. Reacting 14 with phenyl (iso- and/or isothio-) cyanate gave the urea derivatives 20a,b. Thiation of 14 with P4S10 furnished 21. The newly synthesized compounds were tested as antimicrobial agents.

RING-OPENING REACTION OF THE 1,3-DIAZETIDINE RING: HYDRAZINOLYSIS OF 2,4-BIS(HETEROARYLIMINO)-1,3-DIAZETIDINE DERIVATIVES

Reaction between 1,3-diaryl-2,4-bis(heteroarylimino)-1,3-diazetidines and anhydrous hydrazine yield 4-aryl-3-heteroarylimino-5-arylamino-2H-2,3-dihydro-1,2,4-triazoles.When methylhydrazine is used instead of hydrazine 1-methyl and, in some cases, 2-methyl derivatives were isolated.A tentative mechanism is proposed for the different compounds, which were fully characterized by mass spectrometry and 1H and 13C n.m.r. spectroscopy.

Alkylation of 4-Amino-3-mercapto-1,2,4-triazin-5(4H)-ones and Oxidation of the Products

4-Amino-1,2,4-triazin-5(4H)-ones were alkylated with different alkylating agents to give N- and S-alkylated products. 4-Amino-3-methylthio-1,2,4-triazin-5(4H)-one (2a) was oxidized at position 5 to give 4-amino-3-methylthio-1,2,4-triazine-5,6(1H,4H)-dione (4) with Br2/H2O, Br2/EtOH or NBS/EtOH, while Br2/MeOH gave 4-amino-6-methoxy-3-methylthio-1,2,4-triazin-5(4H)-one (8a).

Herbicidally active 1,2,4-triazin-5-one derivatives

Herbicidally active derivatives of the formula STR1 in which R represents methyl, ethyl or n-propyl.

Herbicidal agents

3-[HYDROGEN-, (UNSUBSTITUTED AND HALO, AMINO, NITRO, ALKYL, ALKANOYL, ALKOXY, ALKYLMERCAPTO, ARYLOXY AND/OR ARYL-MERCAPTO-SUBSTITUTED) ALIPHATIC-, CYCLOALIPHATIC-, ARALIPHATIC-, ARYL-, OR HETEROCYCLIC- -SUBSTITUTED OXY, MERCAPTO OR AMINO]4-[AMINO; MONO AND DI (UNSUBSTITUTED AND CYANO, HYDROXY AND/OR HALO-SUBSTITUTED) ALKYL- AND/OR ALKANOYL-AMINO; N-heterocyclic; or N-(unsubstituted and aryl, haloaryl, alkoxyaryl, nitroaryl and/or heterocyclic- substituted) alkylidene or cycloalkylidene]-6-[(unsubstituted and halo, nitro, carbo lower alkoxy, alkyl, alkoxy, alkylmercapto, aralkylmercapto, aryloxy and/or arylmercapto-substituted) aliphatic, cycloaliphatic, araliphatic, aryl, or heterocyclic]-1,2,4-triazine-5-ones, which possess herbicidal properties, and which may be produced by conventional methods.