. 2018 Aug 23;23(9):2116. doi: 10.3390/molecules23092116

Table 2.

Bioactivity of compounds (4a–4x and 8a–8n) through growth inhibition method (inhibition rate %, herbicide activity at 500 mg/L and fungicide activity at 50 mg/L).

Compound	Substituent Group		Herbicidal Activity				Fungicide Activity
	R	X	Brassica campestris		Echinochloca crus-galli		C. arachidicola	B. cinerea	G. zeae	S. sclerotiorum	R. cerealis	P. sasakii
	R	X	Root	Stem	Root	Stem	C. arachidicola	B. cinerea	G. zeae	S. sclerotiorum	R. cerealis	P. sasakii
4a	7-ethoxybenzofuran	/	0	0	0	0	46.24 ± 1.63	30.24 ± 2.94	19.18 ± 1.63	97.18 ± 2.16	0	39.65 ± 4.32
4b	pyridin-2-yl	/	0	0	4.15 ± 1.63	0	31.24 ± 1.63	50.95 ± 0.82	26.34 ± 3.56	85.35 ± 2.94	9.46 ± 1.41	43.96 ± 2.16
4c	pyridin-3-yl	/	31.30 ± 2.16	6.12 ± 1.63	14.24 ± 2.45	25.59 ± 2.45	8.57 ± 1.41	0	19.57 ± 1.63	96.09 ± 2.94	9.94 ± 3.74	30.28 ± 1.41
4d	pyridin-4-yl	/	43.12 ± 5.35	0	26.32 ± 2.94	10.37 ± 1.41	31.36 ± 2.16	21.28 ± 0.82	26.02 ± 0.82	98.12 ± 1.63	9.42 ± 7.12	0
4e	6-CF₃-pyridin-2-yl	/	0	0	73.85 ± 9.27	36.22 ± 1.41	27.97 ± 1.63	60.43 ± 0.82	43.86 ± 2.16	81.39 ± 1.63	14.97 ± 2.16	28.66 ± 3.56
4f	thiophene-2-yl	/	0	0	0	0	46.52 ± 1.41	35.28 ± 1.63	37.56 ± 1.41	73.92 ± 3.56	39.38 ± 7.12	63.17 ± 1.63
4g	furan-2-yl	/	27.21 ± 3.74	0	25.24 ± 1.41	10.26 ± 2.16	42.30 ± 2.16	33.37 ± 0.82	65.26 ± 5.89	100	17.49 ± 2.83	52.28 ± 2.94
4h	Ph	/	0	0	23.32 ± 4.32	7.15 ± 2.94	31.61 ± 0.82	70.29 ± 0.82	30.15 ± 0.82	100	9.28 ± 4.32	0
4i	2-CF₃-Ph	/	0	0	0	0	15.23 ± 2.83	50.49 ± 0.82	22.50 ± 8.29	96.01 ± 2.83	0	0
4j	3-CF₃-Ph	/	0	0	22.18 ± 3.74	5.18 ± 2.16	23.06 ± 0.82	30.58 ± 2.94	15.35 ± 1.63	100	4.55 ± 1.41	43.09 ± 6.98
4k	4-CF₃-Ph	/	17.02 ± 1.63	0	0	0	8.41 ± 0.82	50.09 ± 1.63	26.64 ± 1.41	100	9.37 ± 8.52	33.17 ± 2.45
4l	3-F-Ph	/	19.65 ± 2.94	23.11 ± 1.41	0	0	46.52 ± 2.94	55.98 ± 1.63	41.53 ± 2.16	96.94 ± 1.63	0	33.92 ± 10.2
4m	4-F-Ph	/	71.14 ± 1.63	45.20 ± 3.56	61.25 ± 2.45	35.38 ± 4.32	0	30.94 ± 2.94	4.29 ± 3.56	96.37 ± 2.83	9.25 ± 1.63	22.40 ± 3.27
4n	2-F-Ph	/	69.30 ± 2.94	22.45 ± 2.94	12.14 ± 2.94	0	31.61 ± 0.82	50.37 ± 0.82	59.58 ± 2.45	94.38 ± 3.74	9.34 ± 2.94	52.38 ± 5.89
4o	2-Cl-Ph	/	19.08 ± 3.27	8.18 ± 3.74	21.15 ± 1.63	5.15 ± 2.94	36.99 ± 2.16	40.29 ± 0.82	57.30 ± 5.35	93.28 ± 2.45	23.36 ± 2.16	24.19 ± 2.94
4p	3-Cl-Ph	/	0	0	0	0	27.16 ± 1.63	45.38 ± 2.16	43.91 ± 0.82	71.30 ± 0.82	14.63 ± 2.94	20.28 ± 0.82
4q	4-Cl-Ph	/	32.25 ± 3.60	57.14 ± 3.56	6.18 ± 2.16	0	27.12 ± 3.56	50.49 ± 4.08	48.64 ± 1.41	69.07 ± 4.97	18.28 ± 2.45	8.07 ± 2.16
4r	2,6-F₂-Ph	/	59.66 ± 3.27	40.02 ± 2.16	0	0	36.35 ± 1.41	60.38 ± 0.82	24.28 ± 0.82	64.32 ± 1.41	18.91 ± 11.43	20.59 ± 2.94
4s	2,4-Cl₂-Ph	/	60.29 ± 1.63	25.30 ± 2.16	2.92 ± 2.16	0	18.81 ± 0.82	65.94 ± 1.63	29.17 ± 1.63	79.59 ± 4.32	14.28 ± 5.72	24.94 ± 1.63
4t	PhOCH₂CH₂	/	54.48 ± 2.94	41.01 ± 2.45	33.45 ± 4.32	10.18 ± 4.32	55.49 ± 2.94	50.28 ± 2.16	48.61 ± 1.41	62.27 ± 5.72	36.97 ± 3.56	32.97 ± 0.82
4u	2,4-Cl₂-PhOCH₂CH₂	/	66.70 ± 0.82	73.15 ± 2.83	83.52 ± 2.16	55.26 ± 2.45	27.61 ± 0.82	65.37 ± 0.82	62.28 ± 1.63	50.38 ± 2.94	36.29 ± 2.94	12.08 ± 2.94
4v	4-NO₂-Ph	/	25 ± 2.45	0	0	0	36.35 ± 1.63	55.28 ± 1.63	43.09 ± 1.41	69.29 ± 2.45	14.52 ± 1.41	28.33 ± 3.74
4w	4-MeO-Ph	/	0	0	58.24 ± 2.45	33.23 ± 2.16	45.19 ± 1.63	75.68 ± 2.94	30 ± 2.45	79.21 ± 1.41	23.88 ± 2.16	12.28 ± 2.16
4x	cyclopropyl	/	0	11.04 ± 1.63	26.40 ± 4.24	10.12 ± 2.16	64.56 ± 2.94	70.64 ± 1.63	33 ± 0.82	79.28 ± 3.27	23.34 ± 3.74	32.17 ± 0.82
8a	3-CF₃-Ph	H	53.15 ± 3.56	17.10 ± 2.16	9.20 ± 3.27	20.02 ± 6.48	47.89 ± 4.97	25.28 ± 4.32	37.17 ± 0.82	85.59 ± 3.56	24.09 ± 2.16	39.16 ± 4.08
8b	3-Cl-Ph	H	56.22 ± 1.63	41.24 ± 2.16	47.48 ± 1.63	16.65 ± 3.74	40.39 ± 0.82	58.46 ± 0.82	40.76 ± 1.41	98.03 ± 1.63	10.29 ± 2.94	43.24 ± 3.56
8c	PhOCH₂CH₂	H	73.27 ± 2.94	60.55 ± 1.41	38.17 ± 3.56	10.15 ± 1.63	53.19 ± 2.16	67.35 ± 1.41	43.16 ± 0.82	93.49 ± 2.16	19.87 ± 4.32	35.49 ± 1.63
8d	2,4-Cl₂-PhOCH₂CH₂	H	76.25 ± 0.82	29.58 ± 2.16	21.18 ± 4.08	5.47 ± 4.32	27.18 ± 1.63	55.88 ± 1.63	40.25 ± 0.82	76.58 ± 2.16	5.24 ± 1.63	24.28 ± 1.41
8e	4-MeO-Ph	H	27.49 ± 2.16	13.22 ± 2.83	43.54 ± 5.89	31.24 ± 4.55	18.49 ± 2.83	50.92 ± 0.82	57.28 ± 6.53	76.19 ± 2.16	9.91 ± 1.41	16.57 ± 2.16
8f	6-CF₃-pyridin-2-yl	H	31.54 ± 3.74	0	21.40 ± 1.41	5.18 ± 1.63	36.48 ± 3.74	55.38 ± 0.82	38.66 ± 3.74	71.49 ± 0.82	27.28 ± 3.74	36.39 ± 3.56
8g	3-CF₃-Ph	CF₃	52.22 ± 6.48	19.44 ± 4.24	15 ± 2.94	0	27.18 ± 1.63	54.19 ± 0.82	69.19 ± 1.63	93.38 ± 2.16	0	35.02 ± 0.82
8h	PhOCH₂CH₂	CF₃	82.48 ± 7.26	72.25 ± 4.55	41.15 ± 1.63	11.08 ± 4.08	27.19 ± 1.41	25.28 ± 2.16	37.17 ± 2.94	95.06 ± 3.74	19.21 ± 2.83	26.89 ± 3.56
8i	3-Cl-Ph	CF₃	48.47 ± 2.94	26.15 ± 2.16	8.18 ± 2.16	0	27.49 ± 3.27	50.94 ± 2.16	62.91 ± 8.83	74.15 ± 1.41	0	24.34 ± 2.83
8j	2-Cl-Ph	CF₃	35.26 ± 4.32	40.25 ± 2.16	20.18 ± 2.16	1.08 ± 0.82	36.52 ± 1.63	20.35 ± 1.41	37.09 ± 2.45	74.27 ± 1.41	14.19 ± 1.63	20.28 ± 9.42
8k	4-Cl-Ph	CF₃	18.30 ± 2.94	29.02 ± 2.45	3.24 ± 1.41	0	9.87 ± 1.41	50.97 ± 2.16	24.28 ± 0.82	83.59 ± 4.55	23.28 ± 1.41	24.19 ± 2.45
8l	4-NO₂-Ph	CF₃	2.19 ± 1.41	0	3.20 ± 2.16	9.20 ± 3.56	27.91 ± 3.27	65.97 ± 0.82	38.17 ± 3.56	57.14 ± 2.94	27.09 ± 4.55	20.28 ± 1.41
8m	4-MeO-Ph	CF₃	12.18 ± 2.94	11.15 ± 3.27	44.18 ± 2.16	13.30 ± 2.45	45.49 ± 1.63	60.68 ± 1.63	62.29 ± 0.82	52.79 ± 7.35	14.68 ± 1.41	16.47 ± 2.16
8n	6-CF₃-pyridin-2-yl	CF₃	4.24 ± 2.94	2.99 ± 2.16	0	0	9.35 ± 2.16	50.94 ± 2.16	38.89 ± 4.55	67.29 ± 8.04	9.53 ± 2.94	36.35 ± 2.16
ZINC12007063	/	/	78.48 ± 2.16	63.22 ± 2.83	66.18 ± 2.16	61.18 ± 3.27	17.29 ± 3.56	24.35 ± 0.82	16.21 ± 1.41	63.94 ± 3.56	36.27 ± 2.16	13.02 ± 1.63
Atrazine	/	/	96.54 ± 1.63	92.45 ± 4.32	92.62 ± 4.32	90.23 ± 2.83	/	/	/	/	/	/
Azoxystrobin	/	/	/	/	/	/	56.49 ± 1.41	71.29 ± 1.63	75.19 ± 2.16	100	88.10 ± 1.41	84.34 ± 2.45

Note: Representative fungi used in this study included B. cinereal, C. arachidicola, G. zeae, P. sasakii, S. sclerotiorum, and R. cerealis; “/” means that which is not detected or non-existent.