Synthesis and bioactivity of rotenone oxime <i>O</i>-ether derivatives

Abstract

ABSTRACT.A series of rotenone oxime O-ether derivatives were synthesized and characterized. All compounds were tested for their insecticidal, miticidal and fungicidal activities against the selected pests and compared with those of rotenone. The results of biological tests show that the rotenone oxime O-ether derivatives have improved insecticidal but weak miticidal activities against M. eparate, N. cincticeps, T. urticae compared with rotenone. The disustituted oxime O-ethers showed novel fungicidal activity against R. solani with an inhibition of 80.7-95.2%.

Antiproliferative Activities and SwissADME Predictions of Physicochemical Properties of Carbonyl Group‐Modified Rotenone Analogues

“…The residue was purified by column chromatography on silica gel (EtOAc/ n ‐hexane=1 : 3) to afford a white solid powder (90 mg, 74 % yield). The benzyl oxime derivative 1 d matched the reported 1 H NMR data [14b] . 1 H NMR (500 MHz, CDCl 3 ) δ 7.80 (d, J =8.6 Hz, 1H), 7.54–7.45 (m, 2H), 7.48–7.35 (m, 3H), 6.47 (s, 1H), 6.45 (d, J =8.6 Hz, 1H), 6.40 (s, 1H), 5.29 (dd, J =50.3, 12.0 Hz, 2H), 5.15 (t, J =8.9 Hz, 1H), 5.06 (s, 1H), 4.90 (s, 1H), 4.80 (d, J =3.2 Hz, 1H), 4.57 (dd, J =12.0, 2.3 Hz, 1H), 4.49 (d, J =2.6 Hz, 1H), 4.21 (d, J =11.9 Hz, 1H), 3.78 (s, 3H), 3.51 (s, 3H), 3.28 (dd, J =15.7, 9.8 Hz, 1H), 2.92 (dd, J =15.7, 8.2 Hz, 1H), 1.76 (s, 3H).…”