Table 2. Syntheses of (S)-E-2-Hydroxybenzylidene lactone derivatives 7–28 and Their Antifungal Activities (EC₅₀±SD).

Compounds R1, R2	Alternaria alternata Japanese pear pathotype	Colletotrichum lagenarium
7: R1=H, R2=H	101±1.67 µM	55% growth at 500 µM
8: R1=2′-OCH3, R2=H	122±21.0 µM	49% growth at 500 µM
9: R1=3′-OCH3, R2=H	181±29.0 µM	65% growth at 500 µM
(S)-3: 4′-OCH3, R2=H (Table 1)	28.8±2.19 µM	77% growth at 500 µM
10: R1=2′-CH3, R2=H	56.9±1.06 µM	60% growth at 500 µM
11: R1=3′-CH3, R2=H	89.1±7.86 µM	173±0.97 µM
12: R1=4′-CH3, R2=H	65.5±8.61 µM	76% growth at 500 µM
13: R1=2′-F, R2=H	99.2±6.60 µM	258±28.0 µM
14: R1=3′-F, R2=H	205±7.41 µM	372±72.9 µM
15: R1=4′-F, R2=H	218±37.3 µM	335±37.6 µM
16: R1=2′-CF3, R2=H	52% growth at 500 µM	61% growth at 500 µM
17: R1=3′-CF3, R2=H	97.1±11.5 µM	209±16.5 µM
18: R1=4′-CF3, R2=H	141±7.84 µM	72% growth at 500 µM
19: R1=4′-OCH3, R2=3-OCH3	173±15.6 µM	50% growth at 500 µM
20: R1=4′-OCH3, R2=4-OCH3	235±9.73 µM	69% growth at 500 µM
21: R1=4′-OCH3, R2=5-OCH3	158±15.6 µM	62% growth at 500 µM
22: R1=4′-OCH3, R2=6-OCH3	56% growth at 500 µM	77% growth at 500 µM
23: R1=4′-OCH3, R2=3-CH3	55% growth at 500 µM	82% growth at 500 µM
24: R1=4′-OCH3, R2=4-CH3	88.1±17.0 µM	71% growth at 500 µM
25: R1=4′-OCH3, R2=5-CH3	53.6±12.4 µM	79% growth at 500 µM
26: R1=4′-OCH3, R2=6-CH3	95% growth at 500 µM	78% growth at 500 µM
27: R1=4′-OCH3, R2=4-F	86.2±12.4 µM	326±31.8 µM
28: R1=4′-OCH3, R2=5-F	126±9.44 µM	79% growth at 500 µM