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Propiconazole
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Name

Propiconazole

 EINECS 262-104-4
CAS No. 60207-90-1 Density 1.39 g/cm3
PSA 49.17000 LogP 3.65340
Solubility 100 mg l-1(2O °C) Melting Point <25 °C
Formula C15H17Cl2N3O2 Boiling Point 479.9 °C at 760 mmHg
Molecular Weight 342.225 Flash Point 244.1 °C
Transport Information UN3082 9/PG 3 Appearance normally provided as a yellow liquid
Safety 36/37-46-60-61-45-16-7 Risk Codes 22-43-50/53-39/23/24/25-23/24/25-11
Molecular Structure Molecular Structure of 60207-90-1 (Propiconazole) Hazard Symbols HarmfulXn, DangerousN, ToxicT, FlammableF
Synonyms

Propiconazol;Wocosin;Tilt;Cane Sett Treatment;CGA 64250;Desmel;1-[[2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2-yl]methyl]-1,2,4-triazole;1H-1,2,4-Triazole,1-[[2-(2,4-dichlorophenyl)- 4-propyl-1,3-dioxolan-2-yl]methyl]-;Proconazole;Radar (insecticide);Juno (pesticide);CGD 92710F;Propiconaozle;cis-trans-1-[2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2-ylmethyl]-1H-1,2,4-triazole;Propiconzaole;1-[[2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2-yl]methyl]-1H-1,2,4-triazole;Propuconazol;

Article Data 28

Propiconazole Synthetic route

288-88-0

1,2,4-Triazole

propiconazole iodide

60207-90-1

Propiconazole

Conditions
ConditionsYield
Stage #1: 1,2,4-Triazole With sodium hydroxide In toluene Reflux;
Stage #2: propiconazole iodide In N,N-dimethyl-formamide at 90 - 100℃; Solvent;		97.5%

C15H19Cl2N4O2(1+)*Br(1-)

60207-90-1

Propiconazole

Conditions
ConditionsYield
Stage #1: C15H19Cl2N4O2(1+)*Br(1-) With hydrogenchloride; sodium nitrite In water at 10 - 20℃; for 2h;
Stage #2: With water at 40℃; Temperature; Alkaline conditions;		94.3%
288-88-0

1,2,4-Triazole

2-(bromomethyl)-2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolane

60207-90-1

Propiconazole

Conditions
ConditionsYield
With ethyltriphenylphosphonium bromide; potassium carbonate In 1-methyl-pyrrolidin-2-one at 130℃; Reagent/catalyst;88.6%

2-(bromomethyl)-2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolane

60207-90-1

Propiconazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: butan-1-ol / 8 h / 90 °C
2.1: hydrogenchloride; sodium nitrite / water / 2 h / 10 - 20 °C
2.2: 40 °C / Alkaline conditions
View Scheme
2234-16-4

1-(2,4-dichlorophenyl)ethan-1-one

60207-90-1

Propiconazole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: dihydrogen peroxide; sodium percarbonate; bromine / 1,2-dichloro-ethane / 20 - 45 °C
2: toluene-4-sulfonic acid / toluene / 4 h / Reflux
3: potassium carbonate / dimethyl sulfoxide / 8 h / Reflux
View Scheme

potassium 1,2,4-triazolate

2-(bromomethyl)-2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolane

60207-90-1

Propiconazole

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide for 8h; Reflux;
77-92-9

citric acid

60207-90-1

Propiconazole

1-[2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2-ylmethyl]-1H-1,2,4-triazol-4-ium dihydrogen citrate

Conditions
ConditionsYield
In methanol at 20℃;99%
75-75-2

methanesulfonic acid

60207-90-1

Propiconazole

1-[2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2-ylmethyl]-1H-1,2,4-triazol-4-ium methanesulfonate

Conditions
ConditionsYield
In methanol at 20℃;99%
98-11-3

benzenesulfonic acid

60207-90-1

Propiconazole

1-[2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2-ylmethyl]-1H-1,2,4-triazol-4-ium benzenesulfonate

Conditions
ConditionsYield
In methanol at 20℃;99%
110-16-7

maleic acid

60207-90-1

Propiconazole

1-[2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2-ylmethyl]-1H-1,2,4-triazol-4-ium maleate

Conditions
ConditionsYield
In methanol at 20℃;98%
In hexane for 1h; Product distribution / selectivity;

Propiconazole History

 Propiconazole was first developed by Janssen Pharmaceutica in 1979.

Propiconazole Specification

1.Introduction of Propiconazole

Propiconazole ,with its cas register number 60207-90-1, is a kind of yellowish, odourless, viscous liquid. It also can be called 1-(2-(2,4-Dichlorophenyl)-4-propyl-1,3-dioxolan-2-ylmethyl)-1H-1,2,4-triazole ; Banner ; CGA-64250 ; CGD 92710F ; Caswell No. 323EE ; Desmel ; EPA Pesticide Chemical Code 122101 ; HSDB 6731 ; Orbit and Propiconazole. Propiconazole should be stored in shady and cool warehouse.

2. Properties of Propiconazole

(1) Index of Refraction: 1.623 (2) Molar Refractivity: 86.41 cm3  (3) Molar Volume: 244.8 cm3
(4) Polarizability: 34.25×10-24cm3  (5) Surface Tension: 48.4 dyne/cm  (6) Density: 1.39 g/cm3
(7) Flash Point: 244.1 °C (8) Enthalpy of Vaporization: 74.44 kJ/mol  (9) Boiling Point: 479.9 °C at 760 mmHg
(10) Vapour Pressure: 2.26E-09 mmHg at 25°C 
 

3.Structure descriptors of Propiconazole

Canonical SMILES: CCCC1COC(O1)(CN2C=NC=N2)C3=C(C=C(C=C3)Cl)Cl
InChI: InChI=1S/C15H17Cl2N3O2/c1-2-3-12-7-21-15(22-12,8-20-10-18-9-19-20)13-5-4-11(16)6-14(13)17/h4-6,9-10,12H,2-3,7-8H2,1H3
InChIKey: STJLVHWMYQXCPB-UHFFFAOYSA-N

4. Safety information of Propiconazole

Hazard Codes: HarmfulXn,DangerousN,ToxicT,FlammableF
Risk Statements: 22-43-50/53-39-23/24/25-11
R22:Harmful if swallowed.
R43:May cause sensitization by skin contact.
R50/53:Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
R39:Danger of very serious irreversible effects.
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed.
R11:Highly flammable.
Safety Statements: 36/37-46-60-61-45-16-7
S36/37:Wear suitable protective clothing and gloves.
S46:If swallowed, seek medical advice immediately and show this container or label.
S60:This material and its container must be disposed of as hazardous waste.
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S16:Keep away from sources of ignition.
S7:Keep container tightly closed.
RIDADR: UN3082 9/PG 3
RTECS: XZ4620000
Low toxicity by ingestion. When heated to decomposition it emits toxic vapors of NOx and Cl−.
 

5. Uses of Propiconazole

Propiconazole is a triazole fungicide used agriculturally on grasses grown for seed, mushrooms, corn, wild rice, peanuts, almonds, sorghum, etc. Propiconazole can be absorbed by the roots, stems and leaves, and plants conduct it upward quickly.

6.Toxicity data of Propiconazole

 

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LC50 inhalation 1264mg/m3/4H (1264mg/m3)   National Technical Information Service. Vol. OTS0543201,
rat LD50 oral 1517mg/kg (1517mg/kg)   Proceedings-British Crop Protection Conference-Pests and Diseases. Vol. -, Pg. 508, 1979.
rat LD50 skin > 4gm/kg (4000mg/kg)   Proceedings-British Crop Protection Conference-Pests and Diseases. Vol. -, Pg. 508, 1979.

 

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