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Triadimefon
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Name

Triadimefon

 EINECS 256-103-8
CAS No. 43121-43-3 Density 1.23 g/cm3
PSA 57.01000 LogP 3.12430
Solubility 0.026 g/100 mL in water Melting Point 82 °C
Formula C14H16ClN3O2 Boiling Point 441.9 °C at 760 mmHg
Molecular Weight 293.753 Flash Point 221 °C
Transport Information UN 2588 Appearance Colorless to pale yellow crystalline solid with a slight odor
Safety 24-37-61-45-36/37 Risk Codes 22-43-51/53-39/23/24/25-23/24/25-11
Molecular Structure Molecular Structure of 43121-43-3 (Triadimefon) Hazard Symbols HarmfulXn, DangerousN, ToxicT, FlammableF
Synonyms

EPA Pesticide Chemical Code 109901;Tidifon;1-(4-Chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one;Triazolone;1-(4-Chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanone;Bayleton PB;Triadimefon [BSI:ISO];2-Butanone, 1- (4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-;1H-1,2,4-Triazole, 1-((tert-butylcarbonyl-4-chlorophenoxy)methyl)-;Tenor;Bayleton special;2-Butanone, 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)- (9CI);Nurex;MEB 6447;Diametom B;Bayleton BM;1-(4-Chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butanone;Bayleton triple;Azocene;Triadimefone [ISO-French];Bayleton;BAY-MEB-6447;Mighty;Reach;Otria 25;1-(4-Chlorophenoxy)-3,3-dimethyl-1-(1,2, 4-triazol-1-yl)-butan-2-one;BAY 6681 F;Bayleton Total;2-Butanone, 1-(4-chlorophenoxy)-3, 3-dimethyl-1-(1,2,4-triazol-1-yl)-;Acizol;Miltek;Adifon;

Article Data 39

Triadimefon Synthetic route

118227-32-0

4-Amino-1-[1-(4-chloro-phenoxy)-3,3-dimethyl-2-oxo-butyl]-4H-[1,2,4]triazol-1-ium; chloride

43121-43-3

1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one

Conditions
ConditionsYield
With hydrogenchloride; sodium nitrite at 0 - 20℃;81%
288-88-0

1,2,4-Triazole

1-(4-chlorophenoxy)-1-chloro-3,3-dimethyl-butan-2-one

43121-43-3

1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide; potassium carbonate In water; acetone; toluene
With hydrogenchloride; sodium hydroxide; potassium carbonate In water; acetone; toluene
With hydrogenchloride; sodium hydroxide; potassium carbonate In water; acetone; toluene
73804-20-3

(R)-1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one

43121-43-3

1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one

Conditions
ConditionsYield
In water pH=6.0; Kinetics; Activation energy; pH-value;
89497-67-6

(S)-1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one

43121-43-3

1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one

Conditions
ConditionsYield
In water pH=6.0; Kinetics; Activation energy; pH-value;
288-36-8

1,2,3-triazole

13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

106-48-9

4-chloro-phenol

43121-43-3

1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one

Conditions
ConditionsYield
Stage #1: 1,2,3-triazole; 1-chloro-3,3-dimethyl-butan-2-one; 4-chloro-phenol With potassium carbonate In dichloromethane at 100℃; for 4h;
Stage #2: With sulfuryl dichloride In dichloromethane at 50℃; for 3h; Temperature; Solvent;
43121-43-3

1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one

triadimenol

Conditions
ConditionsYield
With aluminum isopropoxide In isopropyl alcohol at 150℃; for 8h; Temperature; Inert atmosphere;99.6%
1765-93-1

4-fluoroboronic acid

43121-43-3

1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one

1527518-40-6

1-(4'-fluorobiphenyl-4-yloxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one

Conditions
ConditionsYield
With palladium on activated charcoal; potassium carbonate; CyJohnPhos In N,N-dimethyl acetamide; water at 80℃; for 48h; Suzuki Coupling; Schlenk technique; Inert atmosphere;98%
43121-43-3

1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one

98-80-6

phenylboronic acid

43121-37-5

1-(biphenyl-4-yloxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one

Conditions
ConditionsYield
With palladium on activated charcoal; potassium carbonate; CyJohnPhos In N,N-dimethyl acetamide; water at 105℃; for 2h; Temperature; Suzuki Coupling; Schlenk technique; Inert atmosphere; Microwave irradiation;97%
With palladium on activated charcoal; potassium carbonate; CyJohnPhos In N,N-dimethyl acetamide; water at 80℃; for 48h; Temperature; Time; Concentration; Reagent/catalyst; Suzuki Coupling; Schlenk technique; Inert atmosphere;85%

2-(1-chloro-cycloprop-1-yl)-2-(2'-chloro-benzyl)-oxirane

43121-43-3

1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one

2-(1-chlorocyclopropyl)-1-(2-chlorophenyl)-3-(2,5-dihydro-1H-1,2,4-triazol-1-yl) propan-2-ol

Conditions
ConditionsYield
With potassium carbonate In methanol at 25℃; for 1h; Reflux;90%

copper(II) choride dihydrate

64-17-5

ethanol

43121-43-3

1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one

[Cu(1-(4-chlorophenoxy)-3,3-dimethyl-1-H(1,2,4-triazole-1-yl)-2-butanone)2Cl2(EtOH)]

Conditions
ConditionsYield
for 6h; Reflux;85%

Triadimefon Chemical Properties


IUPAC Name: 1-(4-Chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one
Molecular Formula: C14H16ClN3O2
Molecular Weight: 293.75 g/mol
SMILES: n1([C@@H](Oc2ccc(Cl)cc2)C(C(C)(C)C)=O)cncn1
InChI: InChI=1/C14H16ClN3O2/c1-14(2,3)12(19)13(18-9-16-8-17-18)20-11-6-4-10(15)5-7-11/h4-9,13H,1-3H3
EINECS: 256-103-8
Classification Code: Agricultural Chemical; Drug / Therapeutic Agent; Fungicide; Fungicide, bactericide, wood preservative; Fungicides, industrial; Mutation data; Pesticides
Product Categories: FUNGICIDE; 2000/60/EC; Alpha sort; ConazolesMethod Specific; Endocrine Disruptors (Draft) Pesticides & Metabolites; EPA; European Community: ISO and DIN; Fungicides; Pesticides; Q-ZAlphabetic; TP-TZMethod Specific; Endocrine Disruptors (Draft)Alphabetic
storage temperature: APPROX 4 °C 
Water Solubility: 0.026 g/100 mL
Index of Refraction: 1.579 
Molar Refractivity: 78.85 cm3 
Molar Volume: 237 cm3 
Polarizability: 31.25×10-24 cm3 
Surface Tension: 42.4 dyne/cm 
Density: 1.23 g/cm3 
Flash Point: 221 °C 
Enthalpy of Vaporization: 69.92 kJ/mol 
Boiling Point: 441.9 °C at 760 mmHg
Melting Point: 82 °C
Vapour Pressure of Triadimefon (CAS NO.43121-43-3): 5.26E-08 mmHg at 25 °C

Triadimefon Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 oral > 500mg/kg (500mg/kg)   Pesticide Manual. Vol. 9, Pg. 831, 1991.
mouse LC50 inhalation 2337mg/m3 (2337mg/m3)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 34(5), Pg. 64, 1990.
mouse LD50 oral 1gm/kg (1000mg/kg)   Pesticide Manual. Vol. 9, Pg. 831, 1991.
quail LD50 oral 1750mg/kg (1750mg/kg)   Pesticide Manual. Vol. 9, Pg. 831, 1991.
rabbit LD50 oral 500mg/kg (500mg/kg)   "Wirksubstanzen der Pflanzenschutz und Schadlingsbekampfungsmittel," Perkow, W., Berlin, Verlag Paul Parey, 1971-1976Vol. -, Pg. -, 1971/1976.
rat LC50 inhalation 2450mg/m3 (2450mg/m3)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 34(5), Pg. 64, 1990.
rat LD50 oral 363mg/kg (363mg/kg)   Defense des Vegetaux. Vol. 31, Pg. 97, 1977.
rat LD50 skin > 5gm/kg (5000mg/kg)   Farm Chemicals Handbook. Vol. -, Pg. C38, 1991.

Triadimefon Safety Profile

Poison by ingestion. Mutation data reported. When heated to decomposition it emits very toxic fumes of Cl− and NOx.
Hazard Codes: HarmfulXn,DangerousN,ToxicT,FlammableF
Risk Statements: 22-43-51/53-39/23/24/25-23/24/25-11 
R22:Harmful if swallowed. 
R43:May cause sensitization by skin contact. 
R51/53: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: 24-37-61-45-36/37
 S24:Avoid contact with skin. 
S37:Wear suitable gloves. 
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.) 
S36/37:Wear suitable protective clothing and gloves.
RIDADR: 2588
RTECS: EL7100000
HazardClass: 6.1(b)
PackingGroup of Triadimefon (CAS NO.43121-43-3): III

Triadimefon Specification

 Triadimefon (CAS NO.43121-43-3), its Synonyms are 1-(1,2,4-Triazoyl-1)-1-(4-chloro-phenoxy)-3,3-dimethylbutanone ; 1-(4-Chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one ; 1-(4-Chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanone ; 1H-1,2,4-Triazole, 1-((tert-butylcarbonyl-4-chlorophenoxy)methyl)- ; Acizol ; Adifon ; Amiral ; Azocene ; Bayleton CF ; Bayleton Total ; Bayleton triple . It is colorless to pale yellow crystalline solid with a slight odor.

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