An unprecedented study of the application of planar chiral
compounds
in antiviral pesticide development is reported. A class of multifunctional
planar chiral ferrocene derivatives bearing α-amino phosphonate
moieties was synthesized. These compounds, exhibiting superior optical
purities, were subsequently subjected to antiviral evaluations against
the notable plant pathogen potato virus Y (PVY). The influence of
the absolute configurations of the planar chiral compounds on their
antiviral bioactivities was significant. A number of these enantiomerically
enriched planar chiral molecules demonstrated superior anti-PVY activities.
Specifically, compound (S
p, R)-9n displayed extraordinary curative activities against
PVY, with a 50% maximal effective concentration (EC50)
of 216.11 μg/mL, surpassing the efficacy of ningnanmycin (NNM,
272.74 μg/mL). The protective activities of compound (S
p, R)-9n had an
EC50 value of 152.78 μg/mL, which was better than
that of NNM (413.22 μg/mL). The molecular docking and defense
enzyme activity tests were carried out using the planar chiral molecules
bearing different absolute configurations to investigate the mechanism
of their antiviral activities against PVY. (S
p
, R)-9n, (S
p
, R)-9o, and NMM all showed
stronger affinities to the PVY-CP than the (R
p
, S)-9n. Investigations into
the mechanisms revealed that the planar chiral configurations of the
compounds played pivotal roles in the interactions between the PVY-CP
molecules and could augment the activities of the defense enzymes.
This study contributes substantial insights into the role of planar
chirality in defending plants against viral infections.