Based
on the widespread use of hydrogen bonds in drug
design, a series of aldisine derivatives containing oxime, oxime ether,
and hydrazone moieties were designed and synthesized, and their antiviral,
larvicidal, and fungicidal activities were evaluated for the first
time. The bioassay results showed that most of these derivatives were
active against tobacco mosaic virus (TMV). Hydrazone derivative 12 showed in vivo inactivation, curative,
and protection activities of 52 ± 4, 49 ± 1, and 52 ±
3% at 500 mg/L, which are comparable to that of the commercial antiviral
drug ningnanmycin (57 ± 3, 56 ± 2, and 59 ± 1%, respectively)
at the same dose. The antiviral mechanism study showed that compound 12 could cause 20S CP (coating protein) disk fusion and disintegration,
thus affecting the assembly of virus particles. The result of molecular
docking indicated that there were obvious hydrogen bonds between compound 12 and TMV CP. Most derivatives were active against larvae
of lepidopteran pests, such as Mythimna separata, Pyrausta nubilalis, and Plutella xylostella. Some compounds also exhibited
larvicidal activities against Culex pipiens; among them compounds 9 and 13 exhibited
larvicidal activities of 0.81 and 1.54 mg/L (LC50), respectively.
Moreover, most of the derivatives showed broad-spectrum fungicidal
activities against 14 kinds of phytopathogenic fungi at 50 mg/L.