79604-49-2

Usage

Chemical class

2-(2,4-Dichloro-phenyl)-5-methyl-2,4-dihydro-[1,2,4]triazol-3-one belongs to the class of triazolone herbicides.

Herbicidal activity

It is known for its herbicidal activity against a wide range of weeds.

Potential applications

It has potential applications in the field of pharmaceuticals and agrochemicals.

Antifungal and antimicrobial properties

It is being studied for its potential use as an antifungal and antimicrobial agent.

Synthesis

It is synthesized through a series of chemical reactions involving chlorination, condensation, and cyclization.

Unique chemical structure

2-(2,4-Dichloro-phenyl)-5-methyl-2,4-dihydro-[1,2,4]triazol-3-one holds promise for various industrial applications due to its unique chemical structure.

Potential biological activities

The compound has potential biological activities, including herbicidal, antifungal, and antimicrobial properties.

Upstream product

• 133902-78-0 4-acetyl-1-(2,4-dichlorophenyl)-3,3-dimethyl-1,2,4-triazolidin-5-one 
• 35117-33-0 acetone-(2,4-dichloro-phenylhydrazone) 
• 103998-84-1 2-(2-(2,4-dichlorophenyl)hydrazono)propanoic acid 
• 554-00-7 2,4-Dichloroaniline 
• 108-90-7 chlorobenzene 

Downstream Products

• 111992-16-6 4,5-dihydro-3-methyl-4-difluoromethyl-1-(2,4-dichlorophenyl)-1,2,4-triazol-5(1H)-one 
• 911497-95-5 1-(2,4-dichlorophenyl)-3-methyl-4-(2-methylbenzyl)-1H-1,2,4-triazol-5(4H)-one 
• 111992-17-7 4,5-dihydro-3-methyl-4-difluoromethyl-1-(2,4-dichloro-5-nitrophenyl)-1,2,4-triazole-5(1H)-one 
• 111992-18-8 2-(5-amino-2,4-dichlorophenyl)-4-(difluoromethyl)-2,4-dihydro-5-methyl-3H-1,2,4-triazol-3-one 
• 122836-35-5 sulfentrazone 
• 1048965-91-8 (E)-methyl 2-(2-((1-(2,4-dichloro-5-(methylsulfonamido)phenyl)-3-methyl-5-oxo-1H-1,2,4-triazol-4(5H)-yl)methyl)phenyl)-2-(methoxyimino)acetate 
• 1048965-94-1 (E)-methyl 2-(2-((1-(2,4-dichloro-5-(phenylsulfonamido)phenyl)-3-methyl-5-oxo-1H-1,2,4-triazol-4(5H)-yl)methyl)phenyl)-3-methoxyacrylate 
• 1048965-92-9 (E)-methyl 2-(2-((1-(2,4-dichloro-5-(ethylsulfonamido)phenyl)-3-methyl-5-oxo-1H-1,2,4-triazol-4(5H)-yl)methyl)phenyl)-3-methoxyacrylate 
• 1257424-18-2 C₂₇H₂₀Cl₂N₄O₇S₃ 
• 122836-64-0 C₁₅H₂₀Cl₂N₄O₇S₃ 
• 1257424-17-1 C₁₂H₁₄Cl₂N₄O₇S₃ 
• 100563-64-2 C₉H₈Cl₂N₄O 
• 100563-34-6 C₉H₆Cl₂N₄O₃ 
• 1048965-89-4 (E)-methyl 2-(2-((1-(2,4-dichloro-5-(methylsulfonamido)phenyl)-3-methyl-5-oxo-1H-1,2,4-triazol-4(5H)-yl)methyl)phenyl)-3-methoxyacrylate 

Relevant academic research and scientific papers

Synthesis method of metolachlor intermediate

The synthesis method comprises the following steps: S1) nitration reaction of chlorobenzene in a nitration reagent to obtain a mixture of o-chloronitrobenzene and p-chloronitrobenzene without separation. S2) The mixture of o-chloronitrobenzene and p-chloronitrobenzene is subjected to catalytic hydrogenation reaction to obtain the mixture of o-chloroaniline and p-chloroaniline, and the product does not need to be separated. S3) The mixture of o-chloroaniline and chloroaniline is subjected to diazotization reaction to obtain the mixture of o-chlorophenylhydrazine and p-chlorophenylhydrazine, and the product does not need to be separated. S4) The mixture of o-chlorophenylhydrazine and p-chlorophenylhydrazine and aldehyde are subjected to a condensation reaction to obtain a triazole ring mixture of Formulae I through a and I through b. S5) The triazole ring mixture is subjected to chlorination reaction to obtain the metolachlor intermediate shown in the formula I. 2, 4 - Dichloroaniline is used as a raw material, the production cost of the metolachlor is reduced, and the supply limitation of the raw material is avoided.

A aryltriazolinones preparation method

The invention discloses a method for preparing aryl triazolinone. The method comprises the following steps: by taking aryl triazolinone as a raw material, taking an oxygen-containing gas or hydrogen peroxide water solution as an oxidant, and taking active carbon as a catalyst, performing oxidation reaction to obtain aryl triazolinone. By adopting the method, a new concept for the synthesis of the aryl triazolinone compound is provided, the hydrogen peroxide solution or the oxygen-containing gas is taken as the oxidant, the active carbon is taken as the catalyst, and the traditional processing modes of hypohalous acid and salt thereof, halogen oxidant or metal compound catalyst are substituted; the halogen and the metal compound are not contained in the wastewater, so that the environment is not polluted; when the optimized active carbon is adopted, the purity and the yield of the product are high. The environment pollution caused by the halogen-containing oxidant and the metal compound is avoided, the production process is clean, the reaction process is environmentally friendly, the product content and the yield are high and the economic and environmental protection benefits are obvious, so that the method is a scientific and environment-friendly novel method for producing the aryl triazolinone compound.

NOVEL FORM OF SULFENTRAZONE, PROCESS FOR ITS PREPARATION AND USE THEREOF

The invention describes a new crystalline form of sulfentrazone and its preparation process. The invention also describes the analyses of the crystal through various analytical methods and the use of the crystal to prepare stable agrochemical formulation. The novel crystal form is particularly suitable for use in herbicidal compositions and in the control of unwanted plant growth.

Design and synthesis of 1-(benzothiazol-5-yl)-1H-1,2,4-triazol-5-ones as protoporphyrinogen oxidase inhibitors

Protoporphyrinogen oxidase (PPO, E.C. 1.3.3.4) is the action target for several structurally diverse herbicides. A series of novel 4-(difluoromethyl)-1- (6-halo-2-substituted-benzothiazol-5-yl)-3-methyl-1H-1,2,4-triazol-5(4H)-ones 2a-z were designed and synthesized via the ring-closure of two ortho-substituents. The in vitro bioassay results indicated that the 26 newly synthesized compounds exhibited good PPO inhibition effects with Ki values ranging from 0.06 to 17.79 μM. Compound 2e, ethyl 2-{[5-(4- (difluoromethyl)-3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl) -6-fluorobenzo-thiazol-2-yl]thio}acetate, was the most potent inhibitor with Ki value of 0.06 μM against mtPPO, comparable to (Ki = 0.03 μM) sulfentrazone. Further green house assays showed that compound 2f (Ki = 0.24 μM, mtPPO), ethyl 2-{[5-(4-(difluoromethyl)-3-methyl-5- oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)-6-fluorobenzothiazol-2-yl]thio} propanoate, showed the most promising post-emergence herbicidal activity with broad spectrum even at concentrations as low as 37.5 g ai/ha. Soybean exhibited tolerance to compound 2f at the dosages of 150 g ai/ha, whereas they are susceptible to sulfentrazone even at 75 g ai/ha. Thus, compound 2f might be a potential candidate as a new herbicide for soybean fields.

Synthesis and crystal structure of 1,2,4-triazol-5(4H)-one derivative

A new triazole compound, C17H15N3OCl2, has been synthesized and the crystal structure was determined by a single crystal X-ray diffraction study. The crystal symmetry is monoclinic, space group P2(1)/n, with a = 8.1479(17) ?, b = 7.9177(17) ?, c = 25.774(

Synthesis and biological activity of novel phenyltriazolinone derivatives

Phenyltriazolinones are one of the most important classes of herbicides targeting the protoporphyrinogen oxidase enzyme. A series of triazolinone derivatives containing a strobilurin pharmacophore were designed and synthesized with the aim of discovering new phenyltriazolinone analogues with high activity. The herbicidal activity of the synthesized compounds was assayed and some of the test compounds displayed moderate herbicidal activity at 150 g ai/ha.

A Convenient Synthesis of 1-Aryl-3-methyl-1,2,4-triazolin-5-ones From the Reaction Between Acetone Arylhydrazones and Acetyl Isocyanate

The reaction of acetone arylhydrazones with acetyl isocyanate gave the corresponding 4-acetyl-1-aryl-3,3-dimethyl-1,2,4-triazolidin-5-ones which eliminated acetone upon hydrolysis to give 1-aryl-3-methyl-1,2,4-triazolin-5-ones.The above transformation can be achieved in one pot by a simple solvent swap.