Nematodes are one of the most adverse pests of the agricultural industry. With over $80 million worth of damages annually, there were no safe and effective methods of pesticides available for commercial use. The present methods pose serious hazards to organic life and the environment. With this motivation, Dr. Alejandro Calderon-Urrea and his team conducted background research at CSU Fresno, and concluded two classes of Nematodes: Caenorhabditis elegans (a free-living nematode) and Meloidogyne incognita (a plant-parasitic nematode) were most affected by nematicides containing a chalcone scaffold. Of the hundred of chalcones screened, three were found to be especially potent. These chalcones were also tested against beneficial soil organisms and concluded that they were safe for use as selective nematicides. Importantly, the mode of action by which the chalcones kill the nematodes has been difficult to elucidate. This led to our collaboration with the Calderon-Urrea group as we were tasked with synthesizing the nematicidal chalcones with a fluorescent moiety to facilitate analysis via in vivo fluorescence microscopy. After extensive synthetic investigations with fluorescein and fluoresceinamine, we recently were successful in coupling the potent chalcones to pyrene in good yields ranging from 50 to 60%. We then scaled up our syntheses and have produced hundreds of milligrams of these fluorescent chalcones and the Calderon-Urrea group will soon assess their efficacy and begin experiments to elucidate the nematicides’ mode of action. Compound design, all synthetic work, and spectral analysis will be presented.

Fluorescent nematicidal chalcones

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