13208-31-6

Usage

Chemical class

Urea derivatives

Usage

Fungicide and herbicide

Purpose

Controlling growth of fungi and weeds in agriculture and horticulture

Physical appearance

White, crystalline solid

Taste

Slightly bitter

Solubility

Sparingly soluble in water

Health and environmental risks

Poses risks to human health and the environment

Safety precautions

Handle and apply with caution according to guidelines

Upstream product

• 1967-27-7 (3-chlorophenyl)urea 
• 102-09-0 bis(phenyl) carbonate 
• 108-42-9 3-chloro-aniline 
• 75-44-5 phosgene 
• 50625-49-5 m-Chlorobenzoyl azide 
• 51-79-6 urethane 
• 20691-89-8 1-methyl-4-piperidinemethanol 
• 2909-38-8 m-chlorophenyl isocyanate 
• 36166-75-3 1-methyl-1,2,3,6-tetrahydropyridine-4-methanol 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 104-94-9 4-methoxy-aniline 
• 100-01-6 4-nitro-aniline 
• 56-40-6 glycine 
• 107-97-1 sarcosine 

Downstream Products

• 61680-22-6 7-chloro-3-(3-chlorophenyl)quinazoline-2,4(1H,3H)-dione 
• 103-71-9 phenyl isocyanate 
• 108-42-9 3-chloro-aniline 
• 825-41-2 3-chloro-4-nitroaniline 
• 1635-61-6 5-chloro-2-nitroaniline 
• 16082-71-6 N-(3-chlorophenyl)phthalimide 
• 16596-00-2 N,N'-bis-(3-chloro-phenyl)-formamidine 
• 7778-12-3 3,3'-Dichlordiphenylcarbodiimid 
• 3023-72-1 piperidine-1-carboxylic acid-(3-chloro-anilide) 

Relevant academic research and scientific papers

Amide-assisted rearrangement of hydroxyarylformimidoyl chloride to diarylurea

A novel amide-assisted rearrangement reaction of hydroxybenzimidoyl chloride has been established for the efficient synthesis of 1,3-diphenylurea derivatives. A variety of electronically and sterically different 1,3-diphenylurea derivatives can be obtained in good to excellent yields, and a proposed reaction mechanism is also presented.

Investigation of active sites using solid state 27Al and 31P MAS NMR in ceramic amorphous aluminophosphate materials prepared from different potassium salts of phosphate for the synthesis of diphenyl urea derivatives

Ceramic amorphous aluminophosphate (CAmAlP) catalysts were prepared by precipitation method using different phosphate salts of potassium such as KH2PO4, K4P2O7 and K2HPO4 as well as H3PO4. The prepared materials were characterized by PXRD, FT-IR, XPS, SEM, BET Surface area, NH3-TPD, 27Al NMR and 31P NMR analytical methods. The catalytic activity of the materials was checked in the synthesis of diphenyl urea (DPU) from aniline and diethyl carbonate, under refluxing conditions. Further, the general application of the catalysts was tested using various substituted anilines. The recyclability of the catalysts was also studied. Uncertainties in percentage yields were calculated to check the reproducible surface properties. The P-XRD, BET Surface area and NH3-TPD results indicated that the materials were amorphous with mesoporous texture, surface areas and acidities in the range 200–260 m2/g and 0.4–0.7 mmol/g respectively. 27Al NMR studies revealed that Al is present in three different coordination states such as tetrahedral, pentagonal and octahedral. The relative percentages of these Al sites depends on the type of the potassium precursor phosphate salt used. Both tetrahedral and pentagonal Al sites in conjunction with each other represented catalytically active sites. An increase in the pentagonal sites contributed to additional increments to the catalytic activity of CAmAlP. The catalyst prepared from KH2PO4 was found to be the best and demonstrated 96% DPU yield.

Preparation method of symmetric urea compound

The invention discloses a preparation method of a symmetric urea compound, which comprises the following steps: by using a hydroxamic acid compound as a raw material, sequentially adding an alkali anda solvent, reacting at 25-50 DEG C for 1-7 hours in an SO2F2 atmosphere, and carrying out aftertreatment on the reaction solution to obtain the symmetric urea compound. According to the invention, cheap, easily available and environment-friendly SO2F2 is used as an accelerant to efficiently promote the generation of an isocyanate intermediate to form a C-N bond. The generation of isocyanate avoids the use of a large amount of halogen or azide dangerous reagents, so that the compound can be used as a green substitute for standard treatment conditions in Curtius rearrangement and Hofmann rearrangement reactions. The amine source in the final product only comes from hydroxylamine, and no additional amine needs to be added, so that the substrate is wide in applicability, and the correspondingsymmetric urea compound can be obtained at a relatively good yield. The operation process is simple, the aftertreatment only needs filtering, and the method is suitable for large-scale preparation.

N,N'-disubstituted urea compound and synthesis method thereof

The invention discloses an N,N'-disubstituted urea compound and a preparation method thereof. N-alkyl acyloxy amide is taken as a raw material and a dichloro(p-cymene)ruthenium(II) dimer complex is taken as a catalyst for carrying out a reaction in an organic solvent under the presence of silver acetate, and the N,N'-disubstituted urea compound is prepared. Compared with the prior art, the methodhas the following advantages that only an amide derivative is taken as a raw material, reaction conditions are mild, the application range of substrates is wide, operation is simple and convenient, the catalyst is low in price, and selectivity of the product is high.

A simple and efficient synthesis of diaryl ureas with reduction of the intermediate isocyanate by triethylamine

Thirty symmetrical diaryl urea derivatives were synthesised in moderate to excellent yields from arylamine and triphosgene with triethylamine as a reducing agent for the intermediate, isocyanate. It was significant that part of the products could be collected in almost quantitative yield without column chromatography. The procedure under mild reaction conditions was tolerant of a wide range of functional groups. The structures of the compounds were determined by NMR, MS and X-ray crystallographic analyses.

Synthesis of unsymmetrical 2-pyridyl ureas via selenium-catalyzed oxidative carbonylation of 2-aminopyridine with aromatic amines

A simple, one-pot, phosgene-free approach to a series of unsymmetrical 2-pyridyl ureas starting from 2-aminopyridine and various aromatic amines is reported for the first time. The procedure employs inexpensive selenium as the catalyst, and carbon monoxide (instead of phosgene) as the carbonyl reagent. The products are obtained in moderate to good yields via selenium-catalyzed oxidative cross-carbonylation of the substrate amines in the presence of oxygen. The selenium functions as a phase-transfer catalyst and can be recovered easily and reused without any significant degradation of its catalytic activity.

Palladium-catalyzed carbonylation of amines: Switchable approaches to carbamates and N,N′-disubstituted ureas

Switchable access to carbamates and ureas has been developed by solvent control palladium-catalyzed carbonylation of aromatic amines under an atmosphere of carbon monoxide. A variety of N-phenylcarbamates and N,N′- diphenylureas was easily synthesized in good to excellent yields from readily available aromatic amines under mild conditions. Copyright

One-pot synthesis of symmetrical 1,3-diarylureas or substituted benzamides directly from benzylic primary alcohols and effective oxidation of secondary alcohols to ketones using phenyliodine diacetate in combination with sodium azide

Benzylic primary alcohols can be directly converted into symmetrical 1,3-diarylureas or substituted benzamides via an one-pot oxidative reaction using the combined reagent of phenyliodine diacetate and sodium azide. This new reaction constitutes a step-economical way to prepare symmetric 1,3-diarylureas or substituted benzamides depending upon the substituents on the phenyl rings of starting alcohols. The sodium acetate generated in situ from the ligand exchange between phenyliodine diacetate and sodium azide plays the pivotal role in the formation of 1,3-diarylureas. In addition, it is also found that various secondary alcohols can be readily oxidized to their corresponding ketones in excellent yields using the same reagent system of phenyliodine diacetate and sodium azide. Generally, secondary alcohols are preferentially oxidized to the corresponding ketones in the presence of primary ones with the limited amounts of phenyliodine diacetate and sodium azide.

Microwave induced improved synthesis of monoaryl thiocarbamides, 1,3-diarylthiocarbamides, 1,3-diarylcarbamides and monoaryl-2,4-dithiobiurets

The 1-arylthiocarbamides (3), 1, 3-diarylthiocarbamides (6), 1,3-diarylcarbamides (7) and 1-aryl-2,4-dithiobiurets (11) have been synthesized by the microwave induced heating of respective reactants for about 30-60 s in solvent free condition. Reaction yields are higher with reduced time, period and without the use of any solvent.

Synthesis of symmetrical ureas by (Diacetoxyiodo)benzene-induced hofmann rearrangement

Amides undergo Hofmann rearrangement by treatment with (diacetoxyiodo) benzene (DAIB) to provide symmetrical ureas in a simple and robust transformation. Georg Thieme Verlag Stuttgart - New York.