N-Benzoyl-N'-phenylurea
chemical compound
N-Benzoyl-N′-phenylurea (BPU) consists of a urea core with a benzoyl amide on one nitrogen and a phenyl group on the other. It is the parent compound of the benzoylurea class of molecules, several of which are commercially useful insecticides, although N-benzoyl-N′-phenylurea itself is not known to have insecticidal properties.
Structure and bonding
Structure of N-benzoyl-N′-phenylurea was first determined in 2010. 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. 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
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. Alternatively N-benzoyl-N′-phenylurea was synthesized in 2010 by hydrolysis of N-benzoyl-N′-phenylthiourea.
Applications
Benzoylphenylureas (BPUs) were first identified in the 1970s as insecticides.
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