Abstract:
In order to find compounds with higher fungicidal activity and analyze the structure-activity relationship of spirocyclic butenolide compounds, a series of novel spirocyclic butenolide derivatives containing fused heterocyclic moiety such as imidazo2,1-
bthiazol-5(6
H)-one, imidazo2,1-
b1,3thiazin-3(2
H)-one and imidazo 2,1-
b1,3thiazine-3,6(2
H,7
H)-dione were designed and synthesized using spirocyclic butenolide as the orientation structure. Their structures were characterized by
1H NMR,
13C NMR and HRMS spectral data. The
in vitro fungicidal activity evaluation results showed that the EC
50 values of compounds
5f and
6f against
Sclerotinia sclerotiorum were 33.2 and 29.8 mg/L, respectively, which were better than that of the commercial fungicide fenamidone (46.8 mg/L). While the EC
50 values of compounds
7b and
7e against
Phytophthora capsici were 45.8 and 43.5 mg/L, which were also better than that of fenamidone (50.7 mg/L). Comparison with lead compounds, their fungicidal activities were higher than that of 2-methylthio analogues and lower than that of 2-arylamino analogues, which indicated that introduction of the fused heterocyclic moiety can improve the fungicidal activities, and the NH group in the structure play a key role in the fungicidal activity.