111992-05-3

Usage

Uses

1. Used in Agricultural Applications:
1-(4-Cl-2-fluorophenyl)-4-difluoromethyl-4,5-dihydro-3-methyl-1H-1,2,4-triazol-5-(1H)one is used as a herbicide for [application reason] controlling the growth of unwanted plants in various crops. Its mode of action involves inhibiting protoporphyrinogen oxidase, which leads to the accumulation of protoporphyrinogen IX and the subsequent disruption of the chlorophyll synthesis, ultimately causing plant death.
2. Used in Research and Development:
In the field of research and development, 1-(4-Cl-2-fluorophenyl)-4-difluoromethyl-4,5-dihydro-3-methyl-1H-1,2,4-triazol-5-(1H)one serves as a valuable compound for studying the mechanisms of protoporphyrinogen oxidase inhibition and its implications in plant physiology. It can also be used to develop new herbicides with improved efficacy and selectivity for specific crops or weed species.
3. Used in Environmental Management:
1-(4-Cl-2-fluorophenyl)-4-difluoromethyl-4,5-dihydro-3-methyl-1H-1,2,4-triazol-5-(1H)one is used in environmental management for [application reason] controlling invasive plant species and managing vegetation in ecologically sensitive areas. Its targeted action on protoporphyrinogen oxidase makes it a suitable candidate for selective weed control without causing harm to non-target plant species.
4. Used in Industrial Applications:
In the industrial sector, 1-(4-Cl-2-fluorophenyl)-4-difluoromethyl-4,5-dihydro-3-methyl-1H-1,2,4-triazol-5-(1H)one can be employed as a component in the formulation of herbicidal products. Its incorporation into these products can enhance their effectiveness in controlling weed growth, thereby increasing agricultural productivity and reducing the need for manual or mechanical weed control methods.
5. Used in Regulatory Compliance:
1-(4-Cl-2-fluorophenyl)-4-difluoromethyl-4,5-dihydro-3-methyl-1H-1,2,4-triazol-5-(1H)one is used in regulatory compliance for [application reason] ensuring that herbicides meet the safety and efficacy standards set by environmental protection agencies. Its role in this context involves providing data on its environmental impact, toxicity, and potential for bioaccumulation, which are crucial for assessing its suitability as a herbicidal active ingredient.

Upstream product

• 75-45-6 Chlorodifluoromethane 
• 111992-04-2 4,5-dihydro-1-(4-chloro-2-fluorophenyl)-3-methyl-5-oxo-1H-1,2,4-triazole 
• 222979-04-6 2-(4-chloro-2-fluoro-5-iodobenzene)-4-(difluoromethyl)-2,4-dihydro-5-methyl-3H-1,2,4-triazol-3-one 

Downstream Products

• 128621-72-7 carfentrazone 

Relevant academic research and scientific papers

Selective fluorination of an aryl triazolinone herbicide intermediate

Fluoroaryl 1,2,4-triazolin-5-ones are an important class of herbicidal compounds useful in a variety of crop protection applications, primarily for the control of grassy and broad-leaf plant species. While a number of different synthetic strategies can be used for the step-wise preparation of these complex molecules, it is generally preferred to introduce fluorine later in the synthetic pathway, since the presence of fluorine and other halogens has a dominant effect on all subsequent synthetic steps. We have investigated the reactions that occur between aryl triazolinones and a variety of fluorination agents, including F2/N2, XeF2, (CF3SO2)2NF, Selectfluor, CF2(OF)2, CF3OF, CH3COOF, and CF3COOF, and have used this knowledge to develop several alternative high-yielding routes to fluoroaryl 1,2,4-triazolin-5-ones. The fluorine introduction strategy and experimental results for a representative example of this important class of compounds are discussed herein.

Synthesis method of intermediate [...][...] and

The invention discloses a method for synthesizing carfentrazone-ethyl and a carfentrazone-ethyl intermediate. The method comprises the following steps: taking 1-(4-chloro-2-fluorophenyl)-3-methyl-1H-1,2,4-triazole-5-ketone as a raw material; carrying out difluoridate methylation, nitrification, catalytic hydrogenation reduction and diazo arylation to obtain 2-chloro-3-{2-chloro-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxygen-1H-1,2,4-triazole-1-radical]-4-fluorophenyl}propionic acid or carfentrazone-ethyl final product. The method disclosed by the invention has the benefits of simplified integral process, mild reaction conditions, high yield, and high quality of products, thereby facilitating industrial production.

Continuous preparation of high purity Bis(fluoroxy)difluoromethane (BDM) at elevated pressure

The invention provides an improved process for preparing bis(fluoroxy)difluoro-methane (BDM) by continuously reacting F2 with CO2 in a reactor containing a fluorination catalyst (e.g., CsF), wherein the process is conducted at a pressure above atmospheric pressure. The process provides BDM of very high purity and very low residual F2.

Regioselective fluorination of phenyl-substituted triazolinones

A process for the preparation of a compound of the Formula I wherein the process comprising the step of treating a compound of the Formula II with a fluorinating agent at a temperature of about 60° to about 120° C. in the presence of an organic solvent to form a compound of the Formula I; wherein: X, R or R′ can optionally be independently protected with a protecting group which is substantially stable to the fluorinating agent; and where X, R, and R′ are described herein.

Process for the preparation of a triazolinone herbicide

A process for preparing an alkyl alpha -2-chloro-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl]-2,4-substituted-benzene-propanoate herbicide, by reacting an alkyl alpha -acetyl-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl]-2,4-disubstituted-benzene-propanoate, Intermediate D, first with sodium hypochlorite, then with a base, and recovering the herbicide. Intermediate D is prepared by reacting a 1-(2, 4-disubstituted-5-halophenyl)-4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazole, Intermediate B, with an alkyl alkanoate in the presence of a palladium catalyst and a tertiary amine. Intermediate B is prepared by reacting a 1-(2,4-disubstituted-phenyl)-4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazole with a halogenating agent in the presence of an acid. The 2,4-substituents are independently selected from halo, alkyl, cycloalkyl, alkoxy, nitro, or hetercyclyl.