Synthesis, Nematicidal Evaluation, and the Structure-Activity Relationship Study of Aurone Derivatives
Xiaofeng Cao1, Mingxia Wang1, Zhong Li1
1Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China.
Abstract:
Plant-parasitic nematodes (PPNs) are one of the major threats to modern agriculture. Chemical nematicides are still required for the management of PPNs. Based on our previous work, the structure of aurone analogues was obtained using a hybrid 3D similarity calculation method (SHAFTS, SHApe-FeaTure Similarity). Thirty-seven compounds were synthesized. The nematicidal activity of target compounds against Meloidogyne incognita (root-knot nematode, M. incognita) was evaluated, and the structure-activity relationship of synthesized compounds was analyzed. The results showed that compound 6 and some of its derivatives exhibited impressive nematicidal activity. Among these compounds, compound 32 bearing 6-F showed the best in vitro and in vivo nematicidal activity. Its lethal concentration 50% after exposure to 72 h (LC50/72 h) value was 1.75 mg/L, and the inhibition rate reached 97.93% in the sand at 40 mg/L. At the same time, compound 32 also exhibited excellent inhibition on egg hatching and moderate inhibition on the motility of Caenorhabditis elegans (C. elegans).
Related Concept Videos
Physical Properties of Amines
Preparation of 1° Amines: Azide Synthesis
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Adrenergic Agonists: Chemistry and Structure-Activity Relationship
Aromatic ring substitutions: Substituting the aromatic ring with –OH groups at positions 3 and 4 yields catecholamines (e.g., epinephrine), which have a high affinity for adrenoceptors. Hydrogen bonding between –OH groups and receptors enhances adrenergic activity.
Separation of...
Local Anesthetics: Chemistry and Structure-Activity Relationship
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
Basicity of Aromatic Amines


