Design, Synthesis, and Insecticidal Evaluation of New Benzoylureas Containing Amide and Sulfonate Groups Based on the Sulfonylurea Receptor Protein Binding Site for Diflubenzuron and Glibenclamide

On the basis of the sulfonylurea receptor (SUR) protein binding site for diflubenzuron and glibenclamide, 15 new benzoylphenylureas containing amide and sulfonate groups were designed and synthesized. Their structures were characterized by 1H nuclear magnetic resonance (NMR) and elemental analysis [...

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Bibliographic Details
Published in:Journal of agricultural and food chemistry 2013-01, Vol.61 (3), p.517-522
Main Authors: Sun, Ranfeng, Wang, Ziwen, Li, Yongqiang, Xiong, Lixia, Liu, Yuxiu, Wang, Qingmin
Format: Article
Language:English
Subjects:
Animals
binding sites
Biological and medical sciences
diflubenzuron
Diflubenzuron - chemical synthesis
Food industries
Fundamental and applied biological sciences. Psychology
glibenclamide
Glyburide - chemical synthesis
insecticidal properties
Insecticides - chemical synthesis
Larva
Magnetic Resonance Spectroscopy
mass spectrometry
Molecular Structure
Moths
nuclear magnetic resonance spectroscopy
Phenylurea Compounds - chemical synthesis
Phenylurea Compounds - chemistry
Plutella xylostella
Protein Binding
Structure-Activity Relationship
Sulfonylurea Receptors - genetics
Sulfonylurea Receptors - metabolism
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Summary:On the basis of the sulfonylurea receptor (SUR) protein binding site for diflubenzuron and glibenclamide, 15 new benzoylphenylureas containing amide and sulfonate groups were designed and synthesized. Their structures were characterized by 1H nuclear magnetic resonance (NMR) and elemental analysis [or high-resolution mass spectrometry (HRMS)]. The larvicidal activities of the new compounds against oriental armyworm and diamondback moth were evaluated. Compound II-3 showed nearly the same level of insecticidal activity against oriental armyworm as commercial insecticide flucycloxuron and, thus, emerged as a new lead compound for the development of new benzoylurea insecticides.
ISSN:0021-8561
1520-5118
DOI:10.1021/jf304468b