6299-94-1

Usage

Uses

Used in Agricultural Industry:
3-Methylbenzo[1,2,4]triazine is used as a herbicide for its selective weed control properties in various crops. Its chemical structure allows it to target specific weeds without causing significant harm to the desired plants, making it a valuable tool in agricultural practices.
The stability and non-volatile nature of 3-Methylbenzo[1,2,4]triazine contribute to its suitability for use in agricultural applications, ensuring that it remains effective over time and does not easily evaporate or disperse into the environment. However, due to its potential harmful effects if ingested or inhaled, it is crucial to handle this chemical with care and follow appropriate safety measures during its application.

InChI:InChI=1/C8H7N3/c1-6-9-7-4-2-3-5-8(7)11-10-6/h2-5H,1H3

Upstream product

• 14674-17-0 acetic acid 2-(2-nitrophenyl)hydrazide 
• 4413-30-3 N,N'-diphenyl-C-methylformazan 
• 6299-91-8 N'-(2-aminophenyl)acetohydrazide 
• 104273-21-4 3-(2-acetamidophenyl)sydnone 
• 3034-19-3 (2-nitrophenyl)hydrazine 
• 1493-27-2 ortho-nitrofluorobenzene 
• 62-53-3 aniline 
• 19591-17-4 o-iodoacetanilide 

Downstream Products

• 95-14-7 1,2,3-Benzotriazole 
• 615-15-6 2-Methyl-1H-benzimidazole 
• 83325-78-4 3-methyl-1,2,4-benzotriazine-2-oxide 
• 51110-87-3 3-methyl-1,2,4-benzotriazine-1-oxide 
• 71503-85-0 3-methyl-1,2,4-benzotriazine-1,4-dioxide 

Relevant academic research and scientific papers

Synthesis of 1,2,4-Benzotriazines via Copper(I) Iodide/1 H -Pyrrole-2-carboxylic Acid Catalyzed Coupling of o -Haloacetanilides and N -Boc Hydrazine

Coupling of o-haloacetanilides and N-Boc hydrazine proceeded at room temperature under the catalysis of CuI/1H-pyrrole-2-carboxylic acid. The coupling products underwent oxidation to afford the azo compounds, which were subjected to deprotection with TFA

Two-step syntheses of 3-methyl and 3-phenyl-1,2,4-benzotriazines

3-Methyl-1,2,4-benzotriazine and some of its derivatives were prepared in moderate yields (50-70%) via a reductive cyclization by a PtO 2-catalyzed hydrogenation of the corresponding 2- nitrophenylhydrazones of the pyruvic acid. The latter comp

Electrochemical reduction of o-nitrophenylhydrazides into 1,2,4-benzotriazines.

Phenylhydroxylamines, obtained in aqueous medium, by electroreduction of o-nitrophenylhydrazides (o-NO2-C6H4-NH-NHCOR), undergo a disproportionation reaction leading finally to the corresponding o-amino compound; the latter partially rearranges into an o-amidophenylhydrazine (o-RCONH-C6H4-NH-NH2).In a basic media, the disproportionation reaction is concurrent with a ring closure of the intermediate hydroxylamine giving rise to a 1,2,4-benzotriazine.The latter is also obtained by anodic oxidation of the amine, mixed with anilide resulting from the hydrazine oxidation.Electroreduction, immediately followed by an anodic oxidation gives rise to about 50percent yield in the expected triazine.In an acidic media, disproportionation is faster, but the resulting amine undergoes a ring closure reaction into dihydrobenzotriazine when R = H or CH3.Subsequent oxidation of the latter gives rise to 75percent yield of the triazine, mixed with N-aminobenzimidazole resulting from the hydrazine.When R = Ph, the amine is stable but only very poor yields of triazine are obtained by anodic oxidation; the major evolution is probably the formation of an unstable benzoylbenzotriazole.Key words: cyclic voltammetry, controlled potential reduction and oxidation, 1,2,4-benzotriazine, 1-amino-2-alkylbenzimidazoles, organic electrosynthesis.

Sydnones as Masked Hydrazines for Heterocycle Formation: Reactions of 3-(2-Substituted Phenyl)sydnones with HCl

In general, reaction of 3-(2-substituted phenyl)sydnones with HCl gives products derived from cleavage of the sydnone ring to the corresponding hydrazine and subsequent cyclization to the side chain.In one case, 3-(2-aminophenyl)sydnone (43), the product obtained, 1-amino-1H-benzimidazole (47), apparently results from nucleophilic interception by the side chain prior to complete cleavage of the sydnone ring.

Pyrido[3,4-e]-1,2,4-triazines and related heterocycles as potential antifungal agents

The preparation and biological activities of a series of pyrido[3,4-e]-1,2,4-triazines, 1,2,4-triazino[5,6-c]quinolines, and related fused triazines are described. Methyl, amino, and acylamino substituents were placed in the pyridyl ring of the former system. Other structural modifications included various alkyl, cycloalkyl, substituted phenyl, and heterocyclic groups in the 3-position of these ring systems. In agar dilution assays, actives in this series inhibited strains of Candida, Aspergillus, Mucor, and Trychophyton species at MIC's of ≤ 16 μg/mL.

OXIDES OF 3-METHYL-1,2,4-BENZOTRIAZINE

The previously prepared 3-methyl-1,2,4-benzotriazine oxide is shown to be the 4-oxide 5.Synthesis and structores of other isomeric and related oxides are described.A modification of a previously described synthesis of 1,2,4-benzotriazines produces purer products in higher yields.