| Summary: | The U.S. Department of Agriculture (USDA) has established research programs to fight the phytopathogen <i>Colletotrichum fragariae</i> and the invasive red imported fire ant, <i>Solenopsis invicta</i>. <i>C. fragariae</i> is known to cause anthracnose disease in fruits and vegetables, while <i>S. invicta</i> is known for its aggressive behavior and painful stings and for being the cause of significant damage to crops, as well as harm to humans and animals. Many plants have been studied for potential activity against <i>C. fragariae</i> and <i>S. invicta</i>. Among the studied plants, <i>Houttuynia cordata</i> Thunb has been shown to contain 2-undecanone, which h is known for its antifungal activity against <i>Colletotrichum gloesporioides</i>. Based on the mean amount of sand removed, 2-undecanone showed significant repellency at 62.5 µg/g, similar to DEET (<i>N</i>,<i>N</i>-diethyl-<i>meta</i>-toluamide), against <i>S. invicta</i>. The 2-Undecanone with an LC<sub>50</sub> of 44.59 µg/g showed toxicity against <i>S. invicta</i> workers. However, neither <i>H. cordata</i> extract nor 2-undecanone had shown activity against <i>C. fragariae</i> despite their known activity against <i>C. gloesporioides</i>, which in turn motivates us in repositioning 2-undecanone as a selected candidate for a Claisen–Schmidt condensation that enables access to several analogs (<b>2a</b>–<b>f</b>). Among the prepared analogs, (<i>E</i>)-1-(3-methylbenzo[b]thiophen-2-yl)dodec-1-en-3-one (<b>2b</b>) and (<i>E</i>)-1-(5-bromothiophen-2-yl)dodec-1-en-3-one (<b>2f</b>) showed promising activity against <i>C. fragariae</i>, revealing a distinctive structural activity relationship (SAR). The generated analogs revealed a clear regioselectivity pattern through forming the C=C alkene bond at position C-1. These data open the window for further lead optimization and product development in the context of managing <i>C. fragariae</i> and <i>S. invicta</i>.
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