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80060-09-9

Basic Information
CAS No.: 80060-09-9
Name: Diafenthiuron
Article Data: 40
Molecular Structure:
Molecular Structure of 80060-09-9 (Diafenthiuron)
Formula: C23H32N2OS
Molecular Weight: 384.586
Synonyms: 3-(2,6-Diisopropyl-4-phenoxyphenyl)-1-tert-butyl-thiourea;1-tert-Butyl-3-(2,6-diisopropyl-4-phenoxyphenyl)thiourea;CGA 106630;N-(2,6-Bis(1-methylethyl)-4-phenoxyphenyl)-N'-(1,1-dimethylethyl)thiourea;Pegasus (pesticide);UNII-22W5MDB01G;
Density: 1.069 g/cm3
Melting Point: 144.6-147.7 °C
Boiling Point: 448.8 °C at 760 mmHg
Flash Point: 225.2 °C
Appearance: White crystalline powder
Hazard Symbols: HarmfulXn
Risk Codes: 20
Safety: 22
Transport Information: UN 2811
PSA: 65.38000
LogP: 7.27450
Synthetic route
80058-85-1

2,6-diisopropyl-4-phenoxyaniline

67-66-3

chloroform

75-64-9

tert-butylamine

80060-09-9

diafenthiuron

Conditions
ConditionsYield
Stage #1: 2,6-diisopropyl-4-phenoxyaniline; chloroform With potassium tert-butylate In 1,4-dioxane; tert-butyl alcohol at 55℃; for 4h;
Stage #2: tert-butylamine With sulfur; potassium tert-butylate In 1,4-dioxane; tert-butyl alcohol at 55℃; for 12h;
52%
80058-93-1

2,6-diisopropyl-4-phenoxy-1-isothiocyanobenzene

80060-09-9

diafenthiuron

Conditions
ConditionsYield
With tert-butylamine In hexane; toluene
80058-85-1

2,6-diisopropyl-4-phenoxyaniline

80060-09-9

diafenthiuron

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: calcium carbonate / chloroform; water / 2 h / 0 °C / Reflux
2: toluene / 12 h / 20 °C
3: tetraphosphorus decasulfide; potassium carbonate / toluene / 0.33 h / Reflux
View Scheme

1-tert-butyl-3-(2,6-di-isopropyl-4-phenoxy-phenyl)urea

80060-09-9

diafenthiuron

Conditions
ConditionsYield
With tetraphosphorus decasulfide; potassium carbonate In toluene for 0.333333h; Reagent/catalyst; Reflux;
74-87-3

methylene chloride

80060-09-9

diafenthiuron

1-tert-butyl-3-(2,6-diisopropyl-4-phenoxyphenyl)-2-methylisothiourea

Conditions
ConditionsYield
With potassium hydroxide In butanone at 70℃; for 4h; Autoclave;98%
74-83-9

methyl bromide

80060-09-9

diafenthiuron

1-tert-butyl-3-(2,6-diisopropyl-4-phenoxyphenyl)-2-methylisothiourea

Conditions
ConditionsYield
Stage #1: diafenthiuron With potassium tert-butylate In toluene for 1h; Autoclave;
Stage #2: methyl bromide In toluene at 60℃; for 4h; Autoclave;
97.7%
77-78-1

dimethyl sulfate

80060-09-9

diafenthiuron

1-tert-butyl-3-(2,6-diisopropyl-4-phenoxyphenyl)-2-methylisothiourea

Conditions
ConditionsYield
With sodium carbonate In dichloromethane at 35℃; for 6h;96.8%
616-38-6

carbonic acid dimethyl ester

80060-09-9

diafenthiuron

1-tert-butyl-3-(2,6-diisopropyl-4-phenoxyphenyl)-2-methylisothiourea

Conditions
ConditionsYield
With sodium methylate In 1-methyl-pyrrolidin-2-one at 180℃; for 3h;90.8%
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Specification

The IUPAC name of Diafenthiuron is 1-tert-butyl-3-[4-phenoxy-2,6-di(propan-2-yl)phenyl]thiourea. With the CAS registry number 80060-09-9, it is also named as N-(2,6-Bis(1-methylethyl)-4-phenoxyphenyl)-N'-(1,1-dimethylethyl)thiourea. The product's categories are acaricides pesticides & metabolites; alpha sort; insecticides; pesticides; thioureas. It is white crystalline powder which is toxic. When heating it will produce toxic nitrogen oxide and sulfur oxides fumes, so the storage environment should be ventilate, low-temperature and dry. Additionally, it is harmful by inhalation, so people should not breathe dust.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 6.00; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 6; (4)ACD/LogD (pH 7.4): 6; (5)ACD/BCF (pH 5.5): 21239.63; (6)ACD/BCF (pH 7.4): 21239.4; (7)ACD/KOC (pH 5.5): 43546.83; (8) ACD/KOC (pH 7.4): 43546.35; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 6; (11)Index of Refraction: 1.582; (12)Molar Refractivity: 120.05 cm3; (13)Molar Volume: 359.5 cm3; (14)Polarizability: 47.59×10-24 cm3; (15)Surface Tension: 42.1 dyne/cm; (16)Enthalpy of Vaporization: 70.73 kJ/mol; (17)Vapour Pressure: 3.02E-08 mmHg at 25°C; (18)Rotatable Bond Count: 6; (19)Tautomer Count: 3; (20)Exact Mass: 384.223534; (21)MonoIsotopic Mass: 384.223534; (22)Topological Polar Surface Area: 65.4; (23)Heavy Atom Count: 27.

Preparation of Diafenthiuron: The following is the production of 4-phenoxy 2,6-Diisopropyl aniline:



The following is the production of 4-phenoxy 2,6-diisopropyl phenyl isocyanate thiosulfate:



The following is the production of Diafenthiuron:




Uses of Diafenthiuron: It is thiourea insecticide and miticide which is mainly used to prevent and kill the pests and mites in cotton, fruit trees, vegetables, ornamental plants, soybeans and other crops. It also can be used to control the red spider on citrus tree and apple tree, the diamondback moth and other pests of cruciferous vegetables.

People can use the following data to convert to the molecule structure.
1. SMILES:S=C(NC(C)(C)C)Nc2c(cc(Oc1ccccc1)cc2C(C)C)C(C)C
2. InChI:InChI=1/C23H32N2OS/c1-15(2)19-13-18(26-17-11-9-8-10-12-17)14-20(16(3)4)21(19)24-22(27)25-23(5,6)7/h8-16H,1-7H3,(H2,24,25,27)

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
duck LD50 oral > 1500mg/kg (1500mg/kg)   Pesticide Manual. Vol. 9, Pg. 240, 1991.
quail LD50 oral > 1500mg/kg (1500mg/kg)   Pesticide Manual. Vol. 9, Pg. 240, 1991.
rat LC50 inhalation 558mg/m3/14H (558mg/m3)   Pesticide Manual. Vol. 9, Pg. 240, 1991.
rat LD50 oral 2068mg/kg (2068mg/kg)   Pesticide Manual. Vol. 9, Pg. 240, 1991.
rat LD50 skin > 2gm/kg (2000mg/kg)   Pesticide Manual. Vol. 9, Pg. 240, 1991.