N-Benzoyl-N'-phenylurea
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| Names | |
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| Preferred IUPAC name
N-(Phenylcarbamoyl)benzamide | |
Other names
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C14H12N2O2 | |
| Molar mass | 240.262 g·mol−1 |
| Appearance | White crystals |
| Density | 1.259 g cm−3 |
| Melting point | 210 to 213 °C (410 to 415 °F; 483 to 486 K) |
Refractive index (nD)
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1.644 |
| Structure | |
| monoclinic | |
| P21/c, No. 14 | |
a = 15.5641(8) Å, b = 4.6564(3) Å, c = 21.1029(15) Å α = 90°, β = 128.716°, γ = 90°
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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N-Benzoyl-N′-phenylurea (BPU) is the parent compound of the benzoylurea class of molecules, several of which are commerically useful insecticides. It consists of a urea core with a benzoyl amide on one nitrogen and a phenyl group on the other.
Structure and bonding
[edit]Structure of N-benzoyl-N′-phenylurea was first determined in 2010.[1] Molecules in this compound are approximately flat and exhibit high charge delocalization. Within the molecule an intramolecular N−H⋅⋅⋅O hydrogen bond is present forming pseudoaromatic 6-membered ring.[2] Additionally intermolecular N−H⋅⋅⋅O hydrogen bonds are also present combining two molecules into a centrosymmetric dimer (8-membered ring is formed).
Carbonyl C=O bond distances are equal to ca. 1.23 Å, C−N distances are in range of 1.34 to 1.41 Å.
Synthesis
[edit]In 1965 N-benzoyl-N′-phenylurea was synthesized when dry N-chlorobenzamide was reacted with phenylisocyanate or refluxed in dry benzene with anhydrous potassium fluoride.[3] Alternatively N-benzoyl-N′-phenylurea was synthesized in 2010 by hydrolysis of N-benzoyl-N′-phenylthiourea.[1]
Applications
[edit]Several BPU derivatives have notable commercial or research applications.
Benzoylphenylureas were first identified in the 1970s as effective inhibitors of chitin biosynthesis in insects. These compounds disrupt molting and development, making them useful as insect growth regulators. BPUs such as lufenuron and diflubenzuron are commonly used for pest control due to their selectivity and low toxicity to vertebrates.[4]
BPUs have also demonstrated antitumor activity. Studies have shown that BPU analogues can inhibit tubulin polymerization, thereby disrupting cell division in cancer cells. These compounds, especially sulfur analogues, have exhibited significant potency against various cancer cell lines, including pancreatic and prostate cancers.[5]
References
[edit]- ^ a b c Okuniewski, Andrzej; Chojnacki, Jarosław; Becker, Barbara (2010). "N-Benzoyl-N′-phenylurea". Acta Crystallogr. E. 66 (2): o414. doi:10.1107/S1600536810001807. PMC 2979815. PMID 21579832.
- ^ Karabıyık, Hasan; Karabıyık, Hande; İskeleli, Nazan (2012). "Hydrogen-bridged chelate ring-assisted π-stacking interactions". Acta Crystallogr. B. 68 (1): 71–79. doi:10.1107/S0108768111052608. PMID 22267560.
- ^ Rand, Leon; Dolinski, Richard (1965). "Reactions Catalyzed By Potassium Fluoride. IV. The Reaction of N-Chlorobenzamide with Potassium Fluoride". J. Org. Chem. 30 (1): 48–49. doi:10.1021/jo01012a010.
- ^ Chen, Li (2007). "Insecticidal Benzoylphenylurea-S-Carbamate: A New Propesticide with Two Effects of Both Benzoylphenylureas and Carbamates". Journal of Agricultural and Food Chemistry. 55 (7): 2659–2663. doi:10.1021/jf063564g.
- ^ Hallur, Gurulingappa (2006). "Benzoylphenylurea Sulfur Analogues with Potent Antitumor Activity". Journal of Medicinal Chemistry. 49 (7): 2357–2360. doi:10.1021/jm051261s.