Discovery of Natural Product‐Based Fungicides (II): Semisynthesis and Biological Activity of Sarisan Attached 3‐Phenylisoxazolines as Antifungal Agents

Abstract

Many phytopathogenic fungi cause severe damage to crop yields. In continuation of our research aimed at the discovery and development of natural products-based fungicides, a series of thirty-one sarisan attached 3phenylisoxazolines were synthesized and evaluated for their antifungal activities against five phytopathogenic fungi (B. cinerea, C. lagenarium, A. solani, F. solani, and F. graminearum). Among all title sarisan derivatives, compounds IV2, IV14 and IV23 showed potent antifungal activity against some phytopathogenic fungi. In particular, compound IV2 exhibited a broad-spectrum and more potent antifungal activity against A. solani, F. solani, and F. graminearum than the commercial fungicide Hymexazol. In addition, compounds IV2, IV14 and IV23 also displayed relative low toxicity on normal NRK-52E cells. This work will give some insights into the development of sarisan derivatives as new fungicide candidates in plant protection.

Screening of Marine Bioactive Antimicrobial Compounds for Plant Pathogens

“…However, the traditional technology of extraction and separation of active ingredients from natural products is inefficient, glossy and complicated. For example, the traditional solvent extraction method is solvent-consuming and time-consuming, the sublimation method and steam distillation method have special requirements for the composition, the two-phase extraction is easy to emulsify and the separation time is long [ 47 ]. Therefore, new extraction and separation technologies were developed to overcome these drawbacks.…”

“…Equisetin (44) and epi-equisetin (45) exhibited striking antibacterial activities to P. syringae and R. cerealis [123]. A number of compounds, including three compounds (46)(47)(48) showing antifungal activities against C. lagrnarium and B. cinerea, were extracted from the marine fungus Trichoderma longibrachiatum [21]. From the marine fungus Nos.…”

Nitrile Oxide, Alkenes, Dipolar Cycloaddition, Isomerization and Metathesis Involved in the Syntheses of 2-Isoxazolines

“…Liu and coworkers described performing 1,3-DP cycloaddition of in situ-generated ArCNO to allylbenzene derivative. In a typical way, several sarisan derivatives equipped with 3,5-disubstituted 2-isoxazolines moieties were synthesized— Scheme 144 [ 153 ].…”

Synthesis, Antifungal Activity, and Molecular Docking Study of Novel 3‐Carene‐Derived 4‐Substituted Phenyl‐1,2,4‐Triazolinthiones Bearing gem‐Dimethylcyclopropane Moiety

“…According to the reported articles, [4–6] plant‐based natural products provide valuable and distinctive skeletons for constructing novel antifungal molecules. 3‐Carene, a natural product containing gem ‐dimethylcyclopropane ring and carbon‐carbon double bond, was found in turpentine [7–9] and various plant essential oils, and displayed diverse pharmacological properties, including antimicrobial, [10,11] anti‐inflammatory, [12] insecticidal [13] and slee p‐ enhancing activities [14] .…”