Prothioconazole Chemical Properties

Melting point:

139.1-144.5°

Boiling point:

486.7±55.0 °C(Predicted)

Density 

1.50±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

6.9(at 25℃)

form 

Solid

color 

White to light yellow

InChI

InChI=1S/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)

InChIKey

MNHVNIJQQRJYDH-UHFFFAOYSA-N

SMILES

N1C=NC(=S)N1CC(C1(Cl)CC1)(O)CC1=CC=CC=C1Cl

LogP

1.770 (est)

EPA Substance Registry System

3H-1,2,4-Triazole-3-thione, 2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-1,2-dihydro- (178928-70-6)

Safety Information

Hazard Codes 

Xi,N

Risk Statements 

51/53

Safety Statements 

61

RIDADR 

UN3077 9/PG 3

WGK Germany 

2

HS Code 

2933998090

Hazardous Substances Data

178928-70-6(Hazardous Substances Data)

Toxicity

LD50 in rats (mg/kg): > 6200 orally; > 2000 dermally; LC50 in rats (mg/m3): > 4990 by inhalation; LC50 (96 hr) in rainbow trout: 1.83 mg/l (Mauler-Machnik)

Prothioconazole Usage And Synthesis

Uses

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

Definition

ChEBI: 2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-1,2-dihydro-1,2,4-triazole-3-thione is a member of the class of triazoles that is 1,2,4-triazole-3-thione substituted at position 2 by a 2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl group. It is a member of monochlorobenzenes, a member of triazoles, a tertiary alcohol, a member of cyclopropanes and a thiocarbonyl compound.

Synthesis

The general procedure for the synthesis of 2-(2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl)-1,2,4-triazolidine-3-thione from 2-(2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl)-1H-1,2,4-triazolidine-3(2H)-thione was carried out as follows: 2-(1-chlorocyclopropan-1-yl)-1-(2- chlorophenyl)-2-hydroxy-3-(1,2,4-triazolidine-5-thioxo-1-)propane IV (34.6 g, 0.10 mol) was dissolved in acetone (50 mL), followed by slow dropwise addition of hydrogen peroxide (0.15 mmol). The reaction mixture was stirred at 25°C for 2 hours. Upon completion of the reaction, sodium sulfite (6.5 g) was added to the reaction solution and stirring was continued for 1 h at room temperature and the end point of the reaction was detected using potassium iodide starch test paper. Water (50 mL) was added to the reaction system, followed by extraction with ethyl acetate (50 mL each time, three times). The organic phases were combined, dried with anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product (35 g, 90% purity). The crude product was recrystallized from toluene to give prothioconazole (31.6 g) as a white solid in 98% yield and 90% purity.

References

[1] Patent: CN106986838, 2017, A. Location in patent: Paragraph 0055; 0056; 0057; 0058; 0061

Prothioconazole(178928-70-6)Related Product Information

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