1821-33-6

Usage

Uses

Used in Agricultural Applications:
1-Benzoyl-3-phenylurea is utilized as a plant growth regulator for the purpose of improving crop yield and quality. Its ability to increase cytokinin levels in plants contributes to the enhancement of various plant physiological processes, such as cell division and stress tolerance, which are crucial for achieving higher agricultural productivity and better crop characteristics.

InChI:InChI=1/C14H12N2O2/c17-13(11-7-3-1-4-8-11)16-14(18)15-12-9-5-2-6-10-12/h1-10H,(H2,15,16,17,18)

Upstream product

• 572-43-0 1,2-Diphenyl-ethane-1,2-dione dioxime 
• 19964-97-7 N-bromobenzamide 
• 4910-32-1 1,3-diphenylcarbamothioate 
• 55-21-0 benzamide 
• 103-71-9 phenyl isocyanate 
• 64-10-8 phenyl carbamate 
• 98-88-4 benzoyl chloride 
• 614-22-2 1-benzoylurea 
• 1821-34-7 N-chlorobenzamide 
• 62-53-3 aniline 
• 4461-33-0 benzoyl isocyanate 
• 35770-74-2 Phenoxymagnesium bromide 
• 71-43-2 benzene 
• 463-71-8 thiophosgene 

Downstream Products

• 55-21-0 benzamide 
• 103-71-9 phenyl isocyanate 
• 5499-34-3 N-Benzoyl-N',N'-pentamethylen-harnstoff 
• 2645-36-5 1-(N-phenylcarbamoyl)piperidine 
• 93-58-3 benzoic acid methyl ester 
• 64-10-8 phenyl carbamate 
• 17013-30-8 N-Benzoyl-N'-benzyl-harnstoff 

Relevant academic research and scientific papers

The Aza-ene Reaction of Heterocyclic Ketene Aminals with 4-Phenyl-1,2,4-triazoline-3,5-dione

Heterocyclic ketene aminals bearing a secondary enamine moiety underwent an efficient aza-ene reaction with 4-phenyl-1,2,4-triazoline-3,5-dione under very mild conditions, while no reaction was observed with their tertiary enamine analogues.

N -Acylbenzotriazoles as Proficient Substrates for an Easy Access to Ureas, Acylureas, Carbamates, and Thiocarbamates via Curtius Rearrangement Using Diphenylphosphoryl Azide (DPPA) as Azide Donor

A diverse range of ureas, N -acylureas, carbamates, and thiocarbamates has been synthesized in good to excellent yields by reacting N -acylbenzotriazoles individually with amines or amides or phenols or thiols in the presence of diphenylphosphoryl azide (DPPA) as a suitable azide donor in anhydrous toluene at 110 °C for 3-4 hours. In this route, DPPA was found to be a good alternative to trimethylsilyl azide and sodium azide for the azide donor in Curtius degradation. The high reaction yields, one-pot and metal-free conditions, straightforward nature, easy handling, use of readily available reagents, and in many cases avoidance of column chromatography are the notable features of the devised protocol.

Pd-Catalyzed Carbonylation of Acyl Azides

Pd-catalyzed reactions of azides with CO to access an isocynate intermediate have been developed extensively in recent years. However, the catalytic carbonylation of sensitive acyl azides has not been reported. Herein, we report a simple Pd-catalyzed carbonylation reaction of acyl azides with broad substrate scope, high efficiency, and simple operation under mild conditions, which provides facile access to acyl ureas. In addition, a mechanistic study was carried out by both experiment and DFT calculation. Control experiments and kinetic study revealed that the real active palladium species were Pd(0). The result of kinetic study suggested that palladium catalyst, azide, and CO were all involved in the turnover-limiting step except for amine. Further DFT study suggested that an unprecedented five-membered palladacycle intermediate was the key intermediate in the carbonylation reaction. ?

An Improved Synthesis of Urea Derivatives from N -Acylbenzotriazole via Curtius Rearrangement

The good leaving tendency of the benzotriazole moiety has been exploited for the synthesis of symmetric, unsymmetric, N -acyl, and cyclic ureas in good yields from N -acylbenzotriazoles by treating the latter with various amines in the presence of TMSN 3 /Et 3 N in a sealed tube. The salient features of the devised protocol includes the high-yield, mild, metal-free, one-pot reaction conditions, and short reaction time. Furthermore, in many cases, no column chromatography is required for the purification.

In situ slow release of isocyanates: Synthesis and organocatalytic application of N-acylureas

A novel, efficient, and operationally simple one-pot synthesis of both, symmetrical and unsymmetrical N-acylureas from carboxamides and in situ generated isocyanates (from N,N-dibromo-p-toluenesulfonamide) in the presence of a mild base at rt is reported. The protocol avoids the tedious isolation and purification steps of hazardous isocyanates. The first application of these acylureas to the catalysis through hydrogen bonding is also demonstrated.

A simple and efficient synthesis of N-benzoyl ureas

A novel, operationally simple, method for the preparation of acyl ureas is described. The procedure is high yielding and tolerant of a wide range of functional groups.

Palladium-catalyzed N -acylation of monosubstituted ureas using near-stoichiometric carbon monoxide

The palladium-catalyzed carbonylation of urea derivatives with aryl iodides and bromides afforded N-benzoyl ureas (20 examples) in yields attaining quantitative via the application of near-stoichiometric amounts of carbon monoxide generated from the decarbonylation of the CO precursor, 9-methylfluorene-9-carbonyl chloride. The synthetic protocol displayed good functional group tolerance. The methodology is also highly suitable for 13C isotope labeling, which was demonstrated through the synthesis of three benzoyl ureas, including the insecticide triflumuron, whereby 13CO was incorporated into the core structure.

Synthesis of 1,2-diketones from β-keto nitriles via a protection-oxidative-decyanation-deprotection protocol

A variety of 1,2-diketones were prepared from -keto nitriles via a three-step protocol including the protection of the ketones with methoxyamine, oxidative decyanation, and microwave-assisted deprotection in the final step. This approach provides a novel and efficient access to a wide scope of symmetric and unsymmetric 1,2-diketones using molecular oxygen as the oxidant in the decyanation process. Georg Thieme Verlag Stuttgart - New York.

New synthesis of aryl and heteroaryl N-acylureas via microwave-assisted palladium-catalysed carbonylation

A new, practical synthesis of aryl and heteroaryl N-acylureas has been developed via palladium-catalysed carbonylation of aryl or heteroaryl halides in the presence of urea nucleophiles. A range of reactions illustrating the wide scope of this reaction was carried out under microwave irradiation, using either carbon monoxide gas in a vessel equipped with a gas inlet adapter, or molybdenum hexacarbonyl as the carbon monoxide source in standard microwave vials. The reactions proceeded in good to excellent yields. To illustrate the usefulness of this method a one-step synthesis of the important insecticide diflubenzuron is reported.

Heterocyclic rearrangements in constrained media. A zeolite-directed photorearrangement of 1,2,4-oxadiazoles

(Chemical Equation Presented) The first intrazeolite-photoinduced rearrangement of a five-membered heterocycle is reported. A completely different behavior compared to solution irradiations has been observed. The zeolite's role in directing the photoreaction of 3-phenyl-1,2,4-oxadiazoles toward the formation of the corresponding 1,3,4-oxadiazoles in a ring contraction-ring expansion route is discussed.