178928-70-6

Basic information

• Product Name: PROTHIOCONAZOLE
• Synonyms: 2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-1,2-dihydro-3H-1,2,4-triazole-3-thione;Prothioconazole PESTANAL;3H-1,2,4-Triazole-3-thione, 2-2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl-1,2-dihydro-;jau 6476;prothioconazole (bsi, pa iso);2-(2-(1-Chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl)-1H-1,2,4-triazole-3(2H)-thione;2-[2-(1-Chloro-cyclopropyl)-3-(2-chlorophenyl)-2-hydroxy-propyl]-1,2-dihydro-3H-1,2,4-Triazol-3-thione
• CAS NO: 178928-70-6
• Molecular Formula: C₁₄H₁₅Cl₂N₃OS
• Molecular Weight: 344.2594
• Mol File: 178928-70-6.mol

Chemical Properties

• Melting Point: 139.1-144.5°
• Boiling Point: 486.7 °C at 760 mmHg
• Flash Point: 248.2 °C
• Appearance: UN3077 9/PG 3
• Density: 1.5 g/cm³
• Vapor Pressure: 2.75E-10mmHg at 25°C
• Refractive Index: 1.697
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 6.9(at 25℃)
• CAS DataBase Reference: PROTHIOCONAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: PROTHIOCONAZOLE(178928-70-6)
• EPA Substance Registry System: PROTHIOCONAZOLE(178928-70-6)

Safety Data

• Hazard Codes: Xi,N
• Statements: 51/53
• Safety Statements: 61
• RIDADR: UN3077 9/PG 3
• WGK Germany: 2
• Hazardous Substances Data: 178928-70-6(Hazardous Substances Data)

Usage

Uses

Prothioconazole is an antifungal metabolite used in agricultural fungicides and herbicides.

InChI:InChI=1/C14H15Cl2N3OS/c15-11-4-2-1-3-10(11)7-14(20,13(16)5-6-13)8-19-12(21)17-9-18-19/h1-4,9,20H,5-8H2,(H,17,18,21)

Upstream product

• 222408-90-4 [2-(1-chlorocyclopropyl-1-yl)-1-(2-chlorophenyl)-2-hydroxy-3-propane]-(1,2,4-triazolidine-3-thiol-1-yl) 
• 1147550-11-5 ammonium thiocyanate 
• 540-72-7 sodium thiocyanide 
• 298-12-4 Glyoxilic acid 
• 7783-06-4 hydrogen sulfide 
• 872-50-4 1-methyl-pyrrolidin-2-one 
• 517-23-7 3-acetyl-2-oxo-4,5-dihydrofuran 
• 2444-36-2 2'-chloro-benzeneacetic acid 
• 51512-09-5 2-(2-chlorophenyl)acetyl chloride 
• 946402-82-0 2-(2-chlorophenyl)-N-methoxy-N-methylacetamide 
• 139297-65-7 1-(1-chlorocyclopropyl)-2-(2-chlorophenyl)ethanone 
• 222408-91-5 [2-(1-chloro-cycloprop-1-yl)-3-(2-chlorophenyl)-2-hydroxy]-propyl-1-hydrazine 

Downstream Products

• 199851-46-2 2-(1-chloro-cyclopropyl)-1-(2-chloro-phenyl)-3-(4-methanesulphonyl-5-thiono-4,5-dihydro-1,2,4-triazol-1-yl)-propan-2-ol 
• 199391-98-5 di-{1-[2-(1-chlorocyclopropyl)-3-(2-chloro-phenyl)-2-hydroxy-propyl-1]-1,2,4-triazol-5-yl} disulphide 
• 199105-36-7 sodium salt of 2-(1-chloro-cyclopropyl)-1-(2-chlorophenyl)-3-(5-mercapto-1,2,4-triazol-1-yl)-propan-2-ol 
• 199110-67-3 2-(1-chloro-cyclopropyl)-1(2-chlorophenyl)-3-[5-(4-chloro-benzoyl-mercapto)-1,2,4-triazol-1-yl]-propan-2-ol 

Relevant articles and documents

AN INDUSTRIAL SCALE PROCESS FOR THE PREPARATION OF PROTHIOCONAZOLE

The present invention relates to an industrial scale process for the preparation of Prothioconazole (I), which is simple, economical, efficient, user and environment friendly, moreover commercially viable with higher yield and greater chemical purity.

Synthesis method and application of prothioconazole

The invention relates to the technical field of chemical drug synthesis, and especially relates to a synthesis method and application of prothioconazole. The synthesis method of prothioconazole comprises the following steps: 1, carrying out an epoxidation reaction on a compound represented by formula IV to obtain a compound represented by formula III; 2, performing nucleophilic addition reaction on the compound of the formula III and triazole to obtain a compound represented by formula II; and 3, carrying out a vulcanization reaction on the compound of the formula II to obtain prothioconazolerepresented by formula I. The prothioconazole is prepared by taking the compound of the formula IV as an initial raw material through the epoxidation reaction, the nucleophilic addition reaction and the vulcanization reaction, so the cost is low, safety and high efficiency are achieved, potential safety hazards are avoided, the overall yield is high, reaction conditions are mild, the raw materialutilization rate is increased, three wastes can be obviously reduced, and the method has certain significance for industrial production.

IMPROVED PROCESS FOR PREPARATION OF INTERMEDIATES

PCT00760 20 ABSTRACT Disclosed herein is a process for preparation of 1-chloro-2-(1- chlorocyclopropyl)-3-(2-chlorophenyl)propan-2-ol (compound of formula (I)) 5 and 2-(1-chlorocyclopropyl)-2-[(2-chlorophenyl)methyl]oxirane (compound of formula (II)).

METHOD OF SYNTHESIZING 1,2,4-TRIAZOLE-3-THIONE COMPOUNDS AND INTERMEDIATES THEREOF

Disclosed is a method of synthesizing 1,2,4-triazole-3-thione compounds and intermediates thereof. The method includes reacting a hydrazine with glyoxylic acid to form a hydrazono acetic acid intermediate followed by reacting the latter with thiocyanate to obtain the 1,2,4-triazole-3-thione compound. The raw materials involved in the present method are readily available, and the reaction is very specific in terms of regioselectivity, resulting in minimum by-product and high product yield. There are neither specific requirements for special equipment nor special operations such as high vacuum, high temperature, anhydrous and oxygen-free manipulations. The process is simple and generates minimum wastes, suitable for industrial production.

Method for continuously producing prothioconazole by using microchannel reactor and microchannel system (by machine translation)

In the microchannel reactor, 2 - (1 - chlorocyclopropyl) -1 - (2 - chlorophenyl) -3 - hydrazine-propan -2 - alcohol is used as a raw material to continuously complete the preparation process of propiconazole through a cyclization and oxidation two-step re

A PROCESS FOR PREPARATION OF FUNGICIDALLY ACTIVE TRIAZOLE COMPOUNDS

The present invention relates to a process for the preparation of fungicidally active triazole compounds wherein said process uses homologous cage amines as the catalyst.

Preparation method of prothioconazole

The invention relates to a preparation method of prothioconazole. The preparation method comprises that a compound IV undergoes a reaction at 20 to 120 DEG C in the presence of an oxidizing agent and a solvent, and after the reaction, the product is treated to form prothioconazole. The preparation method has mild reaction conditions, utilizes cheap and easily available raw materials, has simple processes, is environmentally friendly and clean in regents and reaction processes, greatly reduces three wastes, is suitable for industrial production, and realizes a high yield of a final product and high content.

Method for synthesizing prothioconazole and optical active body thereof and intermediate

The invention discloses a method for synthesizing prothioconazole and an optical active body thereof and an intermediate. According to the method, a hydrazine compound and glyoxylic acid react to obtain a hydrazono acetic acid intermediate, and then the hydrazono acetic acid intermediate reacts with thiocyanate to obtain a prothioconazole target product. The reaction regioselectivity is good, few side products are generated, and the yield is high. The requirement for equipment is not high, and anhydrous and anaerobic operation is not needed. The process is simple, few three wastes are generated, and the method is suitable for industrial production.