128639-02-1

Basic information

• Product Name: CARFENTRAZONE-ETHYL
• Synonyms: AFFINITY;ETHYL 2-CHLORO-3-[2-CHLORO-4-FLUORO-5-[4-(DIFLUOROMETHYL)-4,5-DIHYDRO-3-METHYL-5-OXO-1H-1,2,4TRIAZOL-1-YL]PHENYL]PROPANOAT;ETHYL-ALPHA,2-DICHLORO-5-[4-(DIFLUOROMETHYL)-4,5-DIHYDRO-3-METHYL-5-OXO-1H-1,2,4-TRIAZOL-1-YL]-4-FLUOROBENZENEPROPANOATE;CARFENTRAZONE-ETHYL;CARFENTRAZON ETHYL;AURORA;Benzenepropanoic acid, .alpha.,2-dichloro-5-4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl-4-fluoro-, ethyl ester;carfentrazone-ethyl (bsi, pa iso)
• CAS NO: 128639-02-1
• Molecular Formula: C₁₅H₁₄Cl₂F₃N₃O₃
• Molecular Weight: 412.19
• Mol File: 128639-02-1.mol

Chemical Properties

• Melting Point: -22.1°
• Boiling Point: bp 760 350-355°
• Flash Point: >110°C
• Appearance: /
• Density: d20 1.457 g/cm3
• Vapor Pressure: 2.05E-08mmHg at 25°C
• Refractive Index: 1.574
• Storage Temp.: 0-6°C
• PKA: -2.26±0.20(Predicted)
• Water Solubility: 21.98mg/L(temperature not stated)
• BRN: 9081231
• CAS DataBase Reference: CARFENTRAZONE-ETHYL(CAS DataBase Reference)
• NIST Chemistry Reference: CARFENTRAZONE-ETHYL(128639-02-1)
• EPA Substance Registry System: CARFENTRAZONE-ETHYL(128639-02-1)

Safety Data

• Hazard Codes: N
• Statements: 50/53
• Safety Statements: 60-61
• RIDADR: UN3082 9/PG 3
• WGK Germany: 2
• RTECS: DA8343383
• Hazardous Substances Data: 128639-02-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C15H14Cl2F3N3O3/c1-3-26-13(24)10(17)4-8-5-12(11(18)6-9(8)16)23-15(25)22(14(19)20)7(2)21-23/h5-6,10,14H,3-4H2,1-2H3

Upstream product

• 140-88-5 ethyl acrylate 
• 111992-05-3 4-difluoromethyl-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 
• 111992-04-2 4,5-dihydro-1-(4-chloro-2-fluorophenyl)-3-methyl-5-oxo-1H-1,2,4-triazole 
• 64-17-5 ethanol 
• 128621-72-7 carfentrazone 

Downstream Products

• 128621-72-7 carfentrazone 

Relevant articles and documents

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.

A method for preparing [...]

The invention relates to the field of compound preparation, and particularly discloses a preparing method of carfentrazone. According to the method, 1-(5-amino-4-chloro-2-fluorophenyl)-4-difluoromethyl-3-methyl-1H-1,2,4,-triazole-5-ketone (hereinafter referred to as substituted aniline) and acrylamide are used as raw materials; 2-chloro-3-{2-chloro-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazole-1-yl]-4-fluorophenyl}propanamide (hereinafter referred to as substituted benzenepropanamide) is obtained through diazo arylation of amino groups; the substituted benzenepropanamide takes an esterification reaction with ethanol under the existence of sulfuric acid; and the carfentrazone is obtained. The preparing method has the advantages that the process is simple; the reaction conditions are mild; the odor of the raw materials and the odor in production environment are small; the product yield is high; and the industrial production can be favorably achieved.

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.

A new and efficient synthetic method for the herbicide carfentrazone-ethyl based on the Heck reaction

The herbicide carfentrazone-ethyl (1) was prepared by a new and improved synthetic method. The common and inexpensive reagent ethyl acrylate was employed to replace commercially unavailable ethyl 3-hydroxy-2-methylenebutanoate, which was used in the synthetic route reported previously. Starting from iodination of 1-(4-chloro-2-fluorophenyl)-4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazole (2), an intermediate 1-(4-chloro-2-fluoro-5-iodophenyl)-4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazole (3) was afforded in an excellent yield. Then, an intermediate ethyl 3-[2-chloro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)-4-fluorophenyl]-2-propenoate (4) was synthesized by Heck coupling of 3 with ethyl acrylate. Next, oxidative addition-elimination of 4 with OXONE/HCl-Et3N in one pot produced ethyl 2-chloro-3-[2-chloro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)-4-fluorophenyl]-2-propenoate (5). Finally, the target product 1 was obtained via reduction of 5 by H2. This new synthetic method exhibits the advantages of mild conditions, atom economy, low-cost, and efficiency.

Preparation method of carfentrazone-ethyl

A preparation method of carfentrazone-ethyl comprises steps of: reacting 1-(5-amino-4-chloro-2-fluorophenyl)-4-difluoromethyl-3-methyl-1H-1,2,4-triazol-5-one with acrylic acid through a diazo arylation reaction to give 2-chloro-3-{2-chloro-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,3-triazol-1-yl]-4-fluorophenyl}propionic acid; and reacting the 2-chloro-3-{2-chloro-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,3-triazol-1-yl]-4-fluorophenyl}propionic acid with ethanol through an esterification reaction in a presence of an acidic catalyst to give carfentrazone-ethyl.

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.

Herbicidal triazolinones

There is provided a method for selectively controlling the weed galium in cereal crops which comprises applying to the locus where control is desired an herbicidally effective amount of the composition wherein, R is halogen, or lower alkyl;, R1 is haloalkyl;, X is hydrogen, halogen, alkyl, haloalkyl, alkoxy, or nitro;, Y is hydrogen, halogen, alkyl, alkoxy, haloalkyl, halo lower alkylsulfinyl, or halo lower alkoxy;, Q is -CH(R2)C(R3)(R4)Q';, R2 is H or halogen;, R3 is halogen;, R4 is H or lower alkyl;, Q' is COOH, COOZ, COOR5, CON(R6)(R7), CN, CHO or C(O)R5;, Z is a salt-forming group;, R5 is alkyl, alkoxycarbonylalkyl, cycloalkyl, aryl, haloaryl, haloalkylaryl, or aralkyl, preferably benzyl;, each of R6 and R7 is, independently, hydrogen or a radical which is alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, phenyl, benzyl or SO2R6 or is one of said radicals substituted by halogen, alkyl or cyano.