68049-83-2

Basic information

• Product Name: azafenidin
• Synonyms: 2-(2,4-dichloro-5-prop-2-ynyloxyphenyl)-5,6,7,8-tetrahydro-1,2,4-triazole(4,3-a)pyridin-3(2H)-one;azafenidin;Evolus;Milestone;2-(2,4-dichloro-5-prop-2-ynyloxypnenyl)-5,6,7,8-tetrahy-dro-1,2,4-trizolo [4,3-α] pyridin-3-(2H)-one;DPX-R 6447;IN-R 6447;R 6447
• CAS NO: 68049-83-2
• Molecular Formula: C₁₅H₁₃Cl₂N₃O₂
• Molecular Weight: 322.194
• Product Categories: Agro-Products, Aromatics, Heterocycles
• Mol File: 68049-83-2.mol

Chemical Properties

• Melting Point: 168-168.5°
• Boiling Point: 468.9°Cat760mmHg
• Flash Point: 237.4°C
• Appearance: /
• Density: 1.43g/cm³
• Vapor Pressure: 5.78E-09mmHg at 25°C
• Refractive Index: 1.65
• PKA: 2.45±0.20(Predicted)
• CAS DataBase Reference: azafenidin(CAS DataBase Reference)
• NIST Chemistry Reference: azafenidin(68049-83-2)
• EPA Substance Registry System: azafenidin(68049-83-2)

Safety Data

• Hazard Codes: T,N
• Statements: 61-48/22-62-50/53
• Safety Statements: 53-45-60-61
• Hazardous Substances Data: 68049-83-2(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 68049-83-2 differently. You can refer to the following data:
1. Azafenidin is a weed controlling herbicide used in various crops.
2. Herbicide.

Metabolic pathway

A common degradation reaction of azafenidin in light, plants and soil is O-dealkylation, and interesting minor reactions in soil are the subsequent methylation of the O-dealkylated degradation product and the reduction of the propynyl group under anaerobic conditions. In soil and light, azafenidin is also readily split to form the triazolinone heterocycle. Azafenidin is readily metabolized in rats and lactating goats through O-dealkylation, hydroxylation of the triazolinone ring in several positions, and glucuronide and sulfate conjugation.

InChI:InChI=1/C15H13Cl2N3O2/c1-2-7-22-13-9-12(10(16)8-11(13)17)20-15(21)19-6-4-3-5-14(19)18-20/h1,8-9H,3-7H2

Upstream product

• 6165-75-9 propargyl benzenesulfonate 
• 68049-71-8 2-(2,4-dichloro-5-hydroxyphenyl)-5,6,7,8-tetrahydro-1,2,4-triazolo[4,3-A]pyridin-3(2H)-one 
• 67669-19-6 N-(2,4-dichloro-5-hydroxyphenyl)acetamide 
• 591-27-5 m-Hydroxyaniline 
• 2304-58-7 5-cyanovaleramide 
• 39807-17-5 2,4-dichloro-5-(2-propynyloxy)aniline 
• 189573-21-5 (2,4-dichloro-5-hydroxy)phenylhydrazine hydrochloride 
• 39489-79-7 4,6-dichloro-1-hydroxy-3-aminobenzene 
• 111-69-3 hexanedinitrile 
• 96232-90-5 methyl N-(4-cyanobutyl)carabamate 

Relevant articles and documents

Discovery and development of a commercial synthesis of azafenidin

A commercial synthesis of the DuPont herbicide azafenidin is described. Discovery of a novel synthesis of the triazolinone ring system and a practical, environmentally benign process to 5-cyanovaleramide were critical breakthroughs in enabling azafenidin to be manufactured at an acceptable cost. The process began with the selective hydrolysis of DuPont's nylon intermediate, adiponitrile, to 5-cyanovaleramide. This was converted via Hofmann rearrangement and Pinner-type cyclization to afford the key amidine carboxylate intermediate containing both carbon atoms of the triazolinone ring. The preservation of all six carbon atoms of adiponitrile set up a 2 + 3 cyclocondensation with arylhydrazines, which replaced a costly 4 + 1 cyclocondensation of an amidrazone with phosgene or a phosgene surrogate used in the original route. This new triazolinone process was optimized to afford the commercial product in a highly efficient and economical fashion.

Process for the preparation of triazolinone herbicides

A process for the preparation of substituted 1,2,4-triazoline-3(2H)-ones of general formula (I) STR1 by reacting an amide of general formula (IV) STR2 with phosgen or thiophosgen or a phosgen substitute or thiophosgen substitute to a compound of general formula V STR3 and subsequent reaction of (V) with a compound of general formula (VI) or of an acid addition salt of (VI) to compounds of general formula (I). Compounds of general formula (I) can be used as herbicides.

Process to prepare herbicidal bicyclic triazoles

This invention includes compounds of Formula II and IV and a process for preparing Formula I compounds by first preparing the compounds of Formula IV and then further reacting to form the compounds of Formula II and further reacting to prepare the compounds of Formula I wherein Q, Z, R2 are as defined within. STR1