Product Name

  • Name

    Difenoconazole

  • EINECS
  • CAS No. 119446-68-3
  • Article Data10
  • CAS DataBase
  • Density 1.41g/cm3
  • Solubility 15 mg/L at 25 °C in water
  • Melting Point 76 °C
  • Formula C19H17Cl2N3O3
  • Boiling Point 547 °C at 760 mmHg
  • Molecular Weight 406.268
  • Flash Point 284.6 °C
  • Transport Information
  • Appearance colorless solid
  • Safety 26-36/37/39
  • Risk Codes 22-41-43
  • Molecular Structure Molecular Structure of 119446-68-3 (Difenoconazole)
  • Hazard Symbols HarmfulXn
  • Synonyms CGA 169374;1H-1,2,4-Triazole,1-[[2-[2-chloro-4-(4- chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan- 2-yl]methyl]-;1-((2-(2-Chloro-4-(4-chlorophenoxy)phenyl)-4-methyl-1,3-dioxolan-2-yl)methyl)-1H-1,2,4-triazole;Difenoconazole 95%TC;Dragon;Score EC 250;Dividend (fungicide);Dividend;Difenoconazol;
  • PSA 58.40000
  • LogP 4.66550

Synthetic route

2-(bromomethyl)-2-(2-chloro-4-(4-chlorophenoxy)phenyl)-4-methyl-1,3-dioxolane

2-(bromomethyl)-2-(2-chloro-4-(4-chlorophenoxy)phenyl)-4-methyl-1,3-dioxolane

difenconazole
119446-68-3

difenconazole

Conditions
ConditionsYield
With potassium hydroxide In dimethyl sulfoxide; N,N-dimethyl-formamide at 140 - 145℃;97.2%
C19H19Cl2N4O3(1+)*Br(1-)

C19H19Cl2N4O3(1+)*Br(1-)

difenconazole
119446-68-3

difenconazole

Conditions
ConditionsYield
Stage #1: C19H19Cl2N4O3(1+)*Br(1-) With hydrogenchloride; sodium nitrite In water at 5 - 20℃; for 2h;
Stage #2: With water at 40℃; Temperature; Alkaline conditions;		95%
1,2,4-Triazole
288-88-0

1,2,4-Triazole

2-(bromomethyl)-2-(2-chloro-4-(4-chlorophenoxy)phenyl)-4-methyl-1,3-dioxolane

2-(bromomethyl)-2-(2-chloro-4-(4-chlorophenoxy)phenyl)-4-methyl-1,3-dioxolane

difenconazole
119446-68-3

difenconazole

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 185℃; for 0.25h; Solvent; Temperature; Reagent/catalyst; Microwave irradiation;92.6%
With trimethyldodecylammonium chloride; potassium hydroxide In 1-methyl-pyrrolidin-2-one at 130℃; Reagent/catalyst;83%
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 163℃; for 5.5h; Temperature;27 g
2-(2,4-dichlorophenyl)-2-bromomethyl-4-methyl-1,3-dioxolane

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

4-chloro-phenol
106-48-9

4-chloro-phenol

potassium 1,2,4-triazolate

potassium 1,2,4-triazolate

difenconazole
119446-68-3

difenconazole

Conditions
ConditionsYield
Stage #1: 2-(2,4-dichlorophenyl)-2-bromomethyl-4-methyl-1,3-dioxolane; potassium-1H-1,2,4-triazol With potassium carbonate In dimethyl sulfoxide at 150℃; for 8h; Green chemistry;
Stage #2: 4-chloro-phenol With potassium carbonate In toluene for 10h; Reflux; Green chemistry;		166.8 g
...Expand
1-(2,4-dichlorophenyl)ethan-1-one
2234-16-4

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

difenconazole
119446-68-3

difenconazole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: dihydrogen peroxide; sodium carbonate; bromine / dichloromethane / 20 - 40 °C / Green chemistry
2.1: toluene-4-sulfonic acid / toluene / 4 h / Reflux; Green chemistry
3.1: potassium carbonate / dimethyl sulfoxide / 8 h / 150 °C / Green chemistry
3.2: 10 h / Reflux; Green chemistry
View Scheme
1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

difenconazole
119446-68-3

difenconazole

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 4 h / 60 °C / Ionic liquid; Green chemistry
2.1: dihydrogen peroxide; sodium carbonate; bromine / dichloromethane / 20 - 40 °C / Green chemistry
3.1: toluene-4-sulfonic acid / toluene / 4 h / Reflux; Green chemistry
4.1: potassium carbonate / dimethyl sulfoxide / 8 h / 150 °C / Green chemistry
4.2: 10 h / Reflux; Green chemistry
View Scheme
difenoconazole nitrate

difenoconazole nitrate

difenconazole
119446-68-3

difenconazole

Conditions
ConditionsYield
With sodium hydroxide In water; toluene at 60℃; pH=8 - 9; Large scale;
4-((2-(2-chloro-4-(4-chlorophenoxy)phenyl)-4-methyl-1,3-dioxolan-2-yl)methyl)-4H-1,2,4-triazole

4-((2-(2-chloro-4-(4-chlorophenoxy)phenyl)-4-methyl-1,3-dioxolan-2-yl)methyl)-4H-1,2,4-triazole

difenconazole
119446-68-3

difenconazole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium hydroxide / water / 11 h / 97 °C
2: hydrogen bromide / 4.5 h / 55 °C
3: potassium carbonate / 1-methyl-pyrrolidin-2-one / 5.5 h / 163 °C
View Scheme
3,4'-Dichlorobiphenyl ether
6842-62-2

3,4'-Dichlorobiphenyl ether

difenconazole
119446-68-3

difenconazole

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: aluminum (III) chloride / 1,2-dichloro-ethane / 10 - 50 °C
2: sulfuric acid / 1,2-dichloro-ethane / Reflux
3: 1-bromo-1,2,4-triazole / 5 - 10 °C
4: potassium hydroxide / dimethyl sulfoxide; N,N-dimethyl-formamide / 140 - 145 °C
View Scheme
1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one
119851-28-4

1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one

difenconazole
119446-68-3

difenconazole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sulfuric acid / 1,2-dichloro-ethane / Reflux
2: 1-bromo-1,2,4-triazole / 5 - 10 °C
3: potassium hydroxide / dimethyl sulfoxide; N,N-dimethyl-formamide / 140 - 145 °C
View Scheme
difenconazole
119446-68-3

difenconazole

difenoconazole nitrate

difenoconazole nitrate

Conditions
ConditionsYield
With nitric acid In benzene at 20℃; for 2h; Solvent; Temperature;84.1%
difenconazole
119446-68-3

difenconazole

2-{2-[2-chloro-4-(4-chlorophenoxy)-phenyl]-4-methyl-[1,3]dioxolan-2-ylmethyl}-2,4-dihydro[1,2,4]triazole-3-thione
186259-71-2

2-{2-[2-chloro-4-(4-chlorophenoxy)-phenyl]-4-methyl-[1,3]dioxolan-2-ylmethyl}-2,4-dihydro[1,2,4]triazole-3-thione

Conditions
ConditionsYield
Stage #1: difenconazole With isopropylmagnesium chloride In tetrahydrofuran at 40℃; for 1.5h;
Stage #2: With sulfur In tetrahydrofuran at 0℃; for 1h;
Stage #3: With hydrogenchloride; water In tetrahydrofuran		59%
hydrogen sulfide
7783-06-4

hydrogen sulfide

difenconazole
119446-68-3

difenconazole

2-[2-chloro-4-(4-chloro-phenoxy)-phenyl]-2-[(5-mercapto-1,2,4-triazol-1-yl)-methyl]-4-methyl-1,3-dioxolan

2-[2-chloro-4-(4-chloro-phenoxy)-phenyl]-2-[(5-mercapto-1,2,4-triazol-1-yl)-methyl]-4-methyl-1,3-dioxolan

Conditions
ConditionsYield
With 1-methyl-pyrrolidin-2-one
With 1-methyl-pyrrolidin-2-one
With 1-methyl-pyrrolidin-2-one
With 1-methyl-pyrrolidin-2-one
With 1-methyl-pyrrolidin-2-one
dimethylsulfoximine
1520-31-6

dimethylsulfoximine

difenconazole
119446-68-3

difenconazole

C21H22Cl2N4O4S

C21H22Cl2N4O4S

Conditions
ConditionsYield
With TEMPO; 3,6‐di‐tert‐butyl‐9‐mesityl‐10‐phenylacridin‐10‐ium tetrafluoroborate; oxygen In acetonitrile at 37℃; for 21h; Sealed tube; Irradiation; regioselective reaction;

Difenoconazole Specification

The IUPAC name of Difenoconazole is 1-[[2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl]methyl]-1,2,4-triazole. With the CAS registry number 119446-68-3, it is also named as Dragon. The product's categories are Alpha Sort; Conazoles Pesticides & Metabolites; D; D Alphabetic; DID - DIN; Fungicides; Pesticides, and the other registry number is 1135441-03-0. Besides, it is colorless solid, which should be stored in sealed place at 0-6 °C. In addition, its molecular formula is C19H17Cl2N3O3 and molecular weight is 406.27.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 4.92; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 4.92; (4)ACD/LogD (pH 7.4): 4.92; (5)ACD/BCF (pH 5.5): 3198.03; (6)ACD/BCF (pH 7.4): 3217.81; (7)ACD/KOC (pH 5.5): 11210.34; (8)ACD/KOC (pH 7.4): 11279.66; (9)#H bond acceptors: 6; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 5; (12)Index of Refraction: 1.641; (13)Molar Refractivity: 103.69 cm3; (14)Molar Volume: 287.1 cm3; (15)Surface Tension: 50.3 dyne/cm; (16)Density: 1.41 g/cm3; (17)Flash Point: 284.6 °C; (18)Melting Point: 76 °C; (19)Water Solubility: 15 mg/L at 25 °C; (20)Enthalpy of Vaporization: 82.62 kJ/mol; (21)Boiling Point: 547 °C at 760 mmHg; (22)Vapour Pressure: 5.09E-12 mmHg at 25 °C.

Uses of Difenoconazole: this chemical is triazole fungicides. It is used as an demethylation inhibitor of sterol. It is also used for the treatment of foliage and seed.

When you are using this chemical, please be cautious about it as the following: it is harmful if swallowed. It is also risk of serious damage to the eyes. Moreover, it may cause sensitization by skin contact. In case of contact with eyes, please rinse immediately with plenty of water and seek medical advice. And you should wear suitable protective clothing, gloves and eye/face protection.

People can use the following data to convert to the molecule structure.
(1)SMILES: Clc4ccc(Oc1ccc(c(Cl)c1)C2(OCC(O2)C)Cn3ncnc3)cc4
(2)InChI: InChI=1/C19H17Cl2N3O3/c1-13-9-25-19(27-13,10-24-12-22-11-23-24)17-7-6-16(8-18(17)21)26-15-4-2-14(20)3-5-15/h2-8,11-13H,9-10H2,1H3
(3)InChIKey: BQYJATMQXGBDHF-UHFFFAOYAF

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
duck LD50 oral > 2150mg/kg (2150mg/kg)   Pesticide Manual. Vol. 9, Pg. 277, 1991.
rabbit LD50 skin > 2010mg/kg (2010mg/kg)   Pesticide Manual. Vol. 9, Pg. 277, 1991.
rat LC50 inhalation > 45mg/m3/4H (45mg/m3)   Pesticide Manual. Vol. 9, Pg. 277, 1991.
rat LD50 oral 1453mg/kg (1453mg/kg)   Pesticide Manual. Vol. 9, Pg. 277, 1991.

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