Design and synthesis of novel 3-(thiophen-2-yl)-1,5-dihydro-2H-pyrrol-2-one derivatives bearing a hydrazone moiety as potential fungicides

Table 1 Antifungal effects of title compounds 5a–5w at 10 μg/mL

Compd.	R¹	R²	R³	Rs	Bc	Cc	Fg
5a	H	4-CH₃	H	10.5 ± 0.5	0.0 ± 8.2	16.4 ± 2.6	7.5 ± 0.5
5b	H	4-CH₃	2-F	67.7 ± 0.5	32.3 ± 0.9	57.3 ± 2.7	28.4 ± 1.1
5c	H	4-CH₃	2-Cl	12.6 ± 1.7	25.3 ± 1.8	21.1 ± 1.3	12.2 ± 1.7
5d	H	4-CH₃	3-Cl	70.6 ± 2.1	49.0 ± 1.6	61.3 ± 1.8	40.6 ± 2.3
5e	H	4-CH₃	4-F	83.9 ± 1.2	49.5 ± 2.2	90.7 ± 1.7	98.6 ± 0.5
5f	H	4-CH₃	4-Cl	76.7 ± 1.5	34.4 ± 0.5	74.7 ± 1.2	69.0 ± 0.6
5g	H	4-CH₃	4-Br	66.7 ± 0.6	66.4 ± 2.1	74.7 ± 1.9	67.4 ± 1.7
5h	H	4-CH₃	4-CF₃	44.1 ± 3.0	38.4 ± 2.4	43.2 ± 2.1	42.3 ± 1.2
5i	H	4-CH₃	2,4-di-Cl	47.5 ± 2.4	40.2 ± 3.1	18.9 ± 2.7	10.8 ± 3.5
5j	H	4-CH₃	4-CH₃	40.7 ± 1.8	27.8 ± 0.7	38.9 ± 1.8	40.5 ± 1.9
5k	H	4-CH₃	4-OCH₃	20.0 ± 3.5	7.3 ± 1.4	25.1 ± 1.0	9.4 ± 2.8
5l	H	H	4-F	52.8 ± 1.1	30.5 ± 3.2	40.7 ± 2.1	38.1 ± 2.1
5m	H	2-Cl	4-F	66.3 ± 1.4	37.5 ± 2.2	50.2 ± 2.8	47.3 ± 1.3
5n	H	2-Br	4-F	91.5 ± 2.0	47.2 ± 1.0	93.0 ± 1.3	53.1 ± 1.1
5o	H	3-Cl	4-F	70.2 ± 1.8	36.1 ± 0.9	73.8 ± 1.2	74.6 ± 3.2
5p	H	4-F	4-F	100.0 ± 0.3	61.1 ± 3.5	100.0 ± 0.2	100.0 ± 0.3
5q	H	4-Cl	4-F	76.4 ± 0.5	37.5 ± 1.4	83.8 ± 1.6	68.6 ± 2.3
5r	H	4-Br	4-F	55.0 ± 1.8	34.7 ± 2.2	48.5 ± 1.6	67.6 ± 3.0
5s	H	2,4-di-Cl	4-F	70.6 ± 3.3	45.8 ± 1.6	43.8 ± 3.0	47.8 ± 1.6
5t	H	4-OCH₃	4-F	67.5 ± 1.2	51.3 ± 2.9	86.0 ± 3.6	92.7 ± 2.5
5u	4-CH₃	4-F	4-F	84.7 ± 1.1	48.5 ± 2.1	53.8 ± 3.3	47.9 ± 1.4
5v	4-CH₃	4-CH₃	4-F	64.7 ± 2.1	36.3 ± 1.8	36.1 ± 1.1	39.6 ± 3.1
5w	4-CH₃	4-CH₃	4-CH₃	37.1 ± 0.1	25.8 ± 0.4	31.2 ± 1.1	35.2 ± 2.1
Drazoxolon ^a	/	/	/	84.5 ± 1.8	91.2 ± 2.2	46.8 ± 1.9	67.2 ± 0.9

Average of three replicates
^a A commercial agricultural fungicide drazoxolon was used for comparison of antifungal activity

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