1792-17-2

Usage

Uses

Used in Agricultural Industry:
Dibutylurea is used as a degradation product for [application reason] in the agricultural industry. It is formed as a result of the breakdown of Benomyl, the active ingredient in Benlate fungicides, which are used to control various fungal diseases in crops.
Used in Environmental and Analytical Chemistry:
Dibutylurea is used as a chemical marker for [application reason] in environmental and analytical chemistry. Its presence can indicate the degradation of Benomyl, which can be useful in monitoring the effectiveness of fungicides and their environmental impact.
Used in Research and Development:
Dibutylurea is used as a research compound for [application reason] in the development of new fungicides and understanding the degradation pathways of existing ones. Its study can contribute to the improvement of agricultural practices and the creation of more effective and environmentally friendly fungicides.

Preparation

The reactions under CO2 pressured conditions were carried out in a stainless steel reactor (SUS 304, 30 mL, TVS-5 type). Thus, butylamine (2.9 g, 40 mmol), Ph3SbO (370 mg, 1.0 mmol), P4S10 (890 mg, 2.0 mmol), and benzene (20 mL) were charged into the reactor, and then CO2 was introduced at a pressure of 4.9 MPa (50 kg cm-2, ca. 65 mmol) at room temperature. The reactor was heated at 80 ℃ in a temperature-regulated incubator for 12 h. When a reaction temperature higher than 100 ℃ was necessary, an oil bath was used. After the heating, the reactor was cooled and carefully decompressed. The contents were treated with hot benzene (3×20 mL) and filtered to remove an insoluble residue containing the catalyst and phosphoric acid derivatives. The collected benzene solution was then concentrated to dryness in vacuo with cooling. Pure 1,3-dibutylurea was isolated by recrystallization from ligroin (yield 2.99 g, 88%).

Synthesis Reference(s)

Synthetic Communications, 21, p. 1923, 1991 DOI: 10.1080/00397919108021783

InChI:InChI=1/C9H20N2O/c1-3-5-7-11(9(10)12)8-6-4-2/h3-8H2,1-2H3,(H2,10,12)

Upstream product

• 590-28-3 potassium cyanate 
• 109-69-3 n-Butyl chloride 
• 142-27-8 carbamic acid-(2-amino-ethyl ester) 
• 109-73-9 N-butylamine 
• 44987-80-6 N-butyl-N'-guanyl-urea 
• 28787-21-5 nitrocarbamoyl-guanidine 
• 57-13-6 urea 
• 3858-78-4 n-butylamine hydrochloride 
• 111-36-4 n-butyl isocyanide 
• 592-82-5 butyl isothiocyanate 
• 55769-51-2 <2-Butylcarbamoyloxy-aethyl>-butylcarbamat 
• 201230-82-2 carbon monoxide 
• 109-65-9 1-bromo-butane 
• 592-31-4 1-butyl-urea 

Downstream Products

• 41862-16-2 6-Amino-1,3-dibutylpyrimidine-2,4(1H,3H)-dione 
• 13909-67-6 N-Butyl-N'-phenylmethansulfonyl-harnstoff 
• 339-43-5 carbutamide 
• 6630-00-8 N-[4-({[(butylamino)carbonyl]amino}sulfonyl)phenyl]acetamide 
• 13909-64-3 N-(butylcarbamoyl)-4-chlorobenzenesulfonamide 
• 13738-74-4 3-(p-nitrobenzenesulfonyl)-1-butylurea 
• 10505-92-7 4-(butylcarbamoyl-sulfamoyl)-benzoic acid ethyl ester 
• 64-77-7 N-[(butylamino)carbonyl]-4-methyl-benzenesulfonamide 
• 109-73-9 N-butylamine 
• 603-54-3 N,N-diphenylurea 
• 5770-40-1 1,3-dibutyl-pyrimidine-2,4,6-trione 
• 56654-52-5 N-nitroso-1,3-dibutylurea 
• 52998-23-9 1,3-di-n-butyl-5,6-diamino-uracil 
• 132716-86-0 6-amino-1,3-di-n-butyl-5-nitroso-uracil 

Relevant academic research and scientific papers

Penicillium expansum lipase-coated magnetic Fe3O 4-polymer hybrid hollow nanoparticles: A highly recoverable and magnetically separable catalyst for the synthesis of 1,3-dibutylurea

Herein, amino-epoxy supports were innovatively imported onto magnetic nanoparticles (Fe3O4-polymer hybrid nanospheres) for immobilizing enzymes. This new support has a coating layer with dual functional groups (epoxy and amino-epoxy). Consequently, this support has great anionic exchange power and a high number of epoxy groups. The acquired immobilized Penicillium expansum lipase in combination with this heterofunctional support represents a novel class of heterogeneous catalyst towards the synthesis of 1,3-dibutylurea from ethylene carbonate and butylamine, which has not been very commonly catalyzed by enzymes. After optimization of the reaction conditions, the yield of 1,3-dibutylurea was 77% under solvent free conditions at 60 °C. Moreover, after completion of reaction, the catalyst was simply recovered by an external conventional magnet and recycled without significant loss in the catalytic activity (up to ten cycles). the Partner Organisations 2014.

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A methodology employing CO2, amines, and phenylsilane was discussed to access aryl- or alkyl-substituted urea derivatives. This procedure was characterized by adopting hydrosilane to promote the formation of ureas directly, without the need to prepare silylamines in advance. Control reactions suggested that FeCl3 was a favorable additive for the generation of ureas, and this 1,5,7-triazabicyclo[4.4.0]dec-5-ene-catalyzed reaction might proceed through nucleophilic addition, silicon migration, and the subsequent formal substitution of silylcarbamate.

METHOD OF PREPARING UREA USING AMINE COMPOUND AND CARBON DIOXIDE

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