80060-09-9

Basic information

• Product Name: Diafenthiuron
• Synonyms: cga106630;n-(2,6-bis(1-methylethyl)-4-phenoxyphenyl)-n’-(1,1-dimethylethyl)-thioure;n-(2,6-bis(1-methylethyl)-4-phenoxyphenyl)-n’-(1,1-dimethylethyl)thiourea;DIAFENTHIURON;1-tert-butyl-3-(2,6-diisopropyl-4-phenoxyphenyl)thiourea;3-(2,6-diisopropyl-4-phenoxyphenyl)-1-tert-butyl-thiourea;PEGASUS;POLO
• CAS NO: 80060-09-9
• Molecular Formula: C₂₃H₃₂N₂OS
• Molecular Weight: 384.58
• Product Categories: INSECTICIDE;AcaricidesPesticides&Metabolites;Alpha sort;D;DAlphabetic;DIA - DICPesticides;Insecticides;Pesticides;Pesticides&Metabolites;Thioureas
• Mol File: 80060-09-9.mol

Chemical Properties

• Melting Point: 144.6-147.7°C
• Boiling Point: 448.8 °C at 760 mmHg
• Flash Point: 149 °C
• Appearance: White crystalline powder
• Density: 1.0367 (rough estimate)
• Vapor Pressure: 3.02E-08mmHg at 25°C
• Refractive Index: 1.5950 (estimate)
• Storage Temp.: 0-6°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 12?+-.0.70(Predicted)
• Merck: 13,2988
• BRN: 8343025
• CAS DataBase Reference: Diafenthiuron(CAS DataBase Reference)
• NIST Chemistry Reference: Diafenthiuron(80060-09-9)
• EPA Substance Registry System: Diafenthiuron(80060-09-9)

Safety Data

• Hazard Codes: Xn
• Statements: 20
• Safety Statements: 22
• RIDADR: UN 2811
• WGK Germany: 2
• RTECS: XN9100000
• HazardClass: 6.1(a)
• PackingGroup: II
• Hazardous Substances Data: 80060-09-9(Hazardous Substances Data)

Usage

Uses

Used in Agriculture:
Diafenthiuron is used as an insecticide for the control of various pests that affect crop yields and quality. Its broad-spectrum action allows it to target a wide range of sucking pests, such as mites, whiteflies, and aphids, which can cause significant damage to crops.
Used in Cotton Production:
In the cotton industry, Diafenthiuron is used as a crucial component in integrated pest management (IPM) programs. Its ability to control all sucking pests of cotton, as well as mites, without harming beneficial insects, makes it an indispensable tool for maintaining healthy and productive cotton crops.
Used in Vegetable and Fruit Cultivation:
Diafenthiuron is also utilized in the cultivation of vegetables and fruits to protect these crops from the detrimental effects of pests. By controlling mites, whiteflies, and aphids, it helps ensure the growth of high-quality produce and contributes to increased yields.
Used in Ornamental Plant Care:
In the context of ornamental plants, Diafenthiuron serves as an effective insecticide to safeguard these plants from pest infestations. Its application helps maintain the aesthetic appeal and health of ornamental plants, making it a valuable asset in horticulture and landscaping.

Toxicology

Diafenthiuron has low toxicity to birds, mammals and beneficial insects, and is only slightly toxic to predatory mites. It is toxic to fish, but presents little hazard because it is rapidly degraded.

Mode of action

Diafenthiuron is a proinsecticide, which means that it must be converted to another compound – the drug – in order to be toxic. Activation of diafenthiuron to its carbodiimide drug occurs on the leaf surface, catalyzed by light, or in the insect, catalyzed by P450 monooxygenases. Diafenthiuron carbodiimide binds to the glutamate residue in the transmembrane F0 subunit of ATP synthase where protons from the intermembrane space dock to begin their journey across the inner mitochondrial membrane. Binding of diafenthiuron carbodiimide to this site blocks proton transport and ATP synthesis. Diafenthiuron was launched in 1991 and resistance has not yet been reported.

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)

Synthetic route

2,6-diisopropyl-4-phenoxyaniline (80058-85-1) + chloroform (67-66-3) + tert-butylamine (75-64-9) → diafenthiuron (80060-09-9)

Conditions	Yield
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%

2,6-diisopropyl-4-phenoxy-1-isothiocyanobenzene (80058-93-1) → diafenthiuron (80060-09-9)

Conditions	Yield
With tert-butylamine In hexane; toluene

2,6-diisopropyl-4-phenoxyaniline (80058-85-1) → diafenthiuron (80060-09-9)

Conditions	Yield
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 → diafenthiuron (80060-09-9)

Conditions	Yield
With tetraphosphorus decasulfide; potassium carbonate In toluene for 0.333333h; Reagent/catalyst; Reflux;

methylene chloride (74-87-3) + diafenthiuron (80060-09-9) → 1-tert-butyl-3-(2,6-diisopropyl-4-phenoxyphenyl)-2-methylisothiourea

Conditions	Yield
With potassium hydroxide In butanone at 70℃; for 4h; Autoclave;	98%

methyl bromide (74-83-9) + diafenthiuron (80060-09-9) → 1-tert-butyl-3-(2,6-diisopropyl-4-phenoxyphenyl)-2-methylisothiourea

Conditions	Yield
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%

dimethyl sulfate (77-78-1) + diafenthiuron (80060-09-9) → 1-tert-butyl-3-(2,6-diisopropyl-4-phenoxyphenyl)-2-methylisothiourea

Conditions	Yield
With sodium carbonate In dichloromethane at 35℃; for 6h;	96.8%

carbonic acid dimethyl ester (616-38-6) + diafenthiuron (80060-09-9) → 1-tert-butyl-3-(2,6-diisopropyl-4-phenoxyphenyl)-2-methylisothiourea

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

Upstream product

• 80058-93-1 2,6-diisopropyl-4-phenoxy-1-isothiocyanobenzene 
• 80058-85-1 2,6-diisopropyl-4-phenoxyaniline 
• 67-66-3 chloroform 
• 75-64-9 tert-butylamine 
• 136337-67-2 1-tert-butyl-3-(2,6-di-isopropyl-4-phenoxy-phenyl)urea 

Relevant articles and documents

Synthesis method of novel thiourea type diafenthiuron for killing insects and mites

The invention relates to a synthesis method of novel thiourea type diafenthiuron for killing insects and mites. According to the invention, each step adopts a method of carrying out reaction during flowing, so that the uniform mixing effect of the materials is further improved, the reaction quality and the reaction rate of the product are improved, and a very good technical effect is achieved.

Thiocarbonyl Surrogate via Combination of Sulfur and Chloroform for Thiocarbamide and Oxazolidinethione Construction

An efficient and practical thiocarbonyl surrogate via combination of sulfur and chloroform has been developed. A variety of thiocarbamides and oxazolidinethiones have been established, including chiral thiourea catalysts and chiral oxazolidinethione auxiliaries with high selectivity. Meanwhile, pesticides Diafenthiuron (an acaricide), ANTU (a rodenticide), and Chloromethiuron (an insecticide) were practically synthesized through this method in gram scale. Dicholorocarbene, as the key intermediate, was further confirmed via a carbene-trapping control experiment.

ACTIVE COMPOUND COMBINATIONS HAVING INSECTICIDAL AND ACARICIDAL PROPERTIES

The novel active compound combinations comprising a compound of the formula (I-1) or (I-2) and the active compounds (1) to (26) listed in the description have very good insecticidal and acaricidal properties.

Cis-Alkoxyspiro-Substituted Tetramic Acid Derivatives

The invention relates to novel cis-alkoxyspiro-substituted tetramic acid derivatives of the formula (I), in which A, G, X, Y and Z are as defined above, to a plurality of processes and intermediates for their preparation and to their use as pesticides and/or herbicides, and also to selective herbicidal compositions comprising firstly cis-alkoxyspiro-substituted tetramic acid derivatives and secondly a crop plant compatibility-improving compound.

SUBSTITUTED SPIROCYCLIC KETOENOLS

The present invention relates to novel substituted spirocyclic ketoenols of the formula (I) in which W, X, Y, Z, A, B, D and G are as defined in the disclosure, to a plurality of processes for their preparation and to their use as pesticides, microbicides and herbicides.

Glyoxyl acid amides, method for producing them and their use for controlling harmful organisms

The invention relates to novel gloyoxylic acid amides, to a process for their preparation and to their use for controlling harmful organisms.

Optically active 2,5-bisaryl-delta1-pyrrolines and their use as pest control agents

Novel optically active Δ1-pyrrolines of the formula (I) in which R1, R2, R1, R4, and m are each as defined in the description, a plurality of the processes for preparing these substances and their use for controlling pests.

Phenyl-substituted 5,6-dihydrophyne derivatives for use as pesticides and herbicides

The present invention relates to novel phenyl-substituted 5,6-dihydro-pyrone derivatives of the formula (I) in which W, X, Y, Z, G, A, B, Q1 and Q2 are each as defined in the description, to a plurality of processes for their preparation and to their use as pesticides and herbicides.

Pyrazolyl biphenyl carboxamides and the use thereof for controlling undesired microorganisms

Novel pyrazolylbiphenylcarboxamides of the formula (I) in which R1, R2, X, m, Y and n are each as defined in the description, a plurality of processes for preparing these substances and their use for controlling undesirable microorganisms, and also novel intermediates and their preparation.

Triazolopyrimidines

The invention relates to novel triazolopyrimidines of the formula 1wherein X represents halogen, Y represents a hydrogen atom or halogen, and R has the meanings given in the disclosure, to a process for the preparation of the new compounds, and to their use as microbicides.