含吡啶环的1-唑基-1,1-二芳基甲烷类化合物的合成及杀菌活性研究

doi:10.6023/cjoc202506035

摘要/Abstract

为探索吡啶杂环对唑类杀真菌剂活性的影响, 以联苯苄唑为先导, 以吡啶二芳酮分子插件为原料, 设计合成了24个含吡啶环的1-唑基-1,1-二芳基甲烷类化合物. 对10种植物病原真菌的离体杀菌活性测定结果表明, 部分化合物对多种病原菌表现出良好的抑制效果, 其中4-([1,1'-联苯]-4-基(1H-1,2,4-三唑-1-基)甲基)-2-氯吡啶(I-12)、1-((4-叔丁基苯基)(3-氯苯基)甲基)-1H-1,2,4-三唑(I-21)、4-((4-叔丁基苯基)(1H-咪唑-1-基)甲基)-2-氯吡啶(I-23)对Sclerotinia sclerotiorum, Fusarium graminearum, Botrytis cinerea, Pythium aphanidermatum等真菌的杀菌活性显著, 化合物I-23对Pythium aphanidermatum的EC₅₀值为14.03 mg/L, 与对照药联苯苄唑(14.87 mg/L)的活性相当. 构效关系分析显示, 咪唑取代的化合物通常活性更高, 而苯环上较大的取代基和化合物的疏水性对活性有积极影响. 分子对接研究进一步揭示了化合物与靶标蛋白可能的结合机制.

关键词: 杀菌剂, 1-唑基-1,1-二芳基甲烷, 杀菌活性, 构效关系, 分子对接

To investigate pyridine influence on azole fungicides, 24 novel pyridine-containing 1-azolyl-1,1-diarylmethane derivatives were synthesized using bifonazole as the lead compound and pyridinyl diaryl ketone molecules plug-in as the raw materials. Their antifungal activities against 10 plant pathogenic fungi were evaluated in vitro. Several compounds exhibited promising inhibitory effects, particularly 4-([1,1'-biphenyl]-4-yl(1H-1,2,4-triazol-1-yl)methyl)-2-chloropyridine (I-12), 1-((4- (tert-butyl)phenyl)(3-chlorophenyl)methyl)-1H-1,2,4-triazole (I-21) and 4-((4-(tert-butyl)phenyl)(1H-imidazol-1-yl)methyl)- 2-chloropyridine (I-23), which showed significant efficacy against Sclerotinia sclerotiorum, Fusarium graminearum, Botrytis cinerea and Pythium aphanidermatum. Notably, compound I-23 showed equivalent efficacy (EC₅₀=14.03 mg/L) to bifonazole (14.87 mg/L) against P. aphanidermatum. Structure-activity relationship analysis revealed that imidazole-substituted derivatives generally exhibited higher activity, where bulky substituents on phenyl rings and increased hydrophobicity positively influenced the fungicidal effects. Molecular docking studies further elucidated the possible binding mechanisms between these compounds and target proteins.

Key words: fungicide, 1-azolyl-1,1-diarylmethanes, fungicidal activity, structure-activity relationship, molecular docking

引用此文

洪赛, 尹发红, 陈明慧, 傅滨, 肖玉梅, 覃兆海. 含吡啶环的1-唑基-1,1-二芳基甲烷类化合物的合成及杀菌活性研究[J]. 有机化学, 2026, 46(1): 106-117.

Hong Sai, Yin Fahong, Chen Minghui, Fu Bin, Xiao Yumei, Qin Zhaohai. Study on the Synthesis and Fungicidal Activity of 1-Azolyl-1,1- diarylmethanes Containing Pyridine Ring[J]. Chinese Journal of Organic Chemistry, 2026, 46(1): 106-117.

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Compd.		Inhibition rate/(%, 50 mg/L)										MIR^c%
Compd.	Log P^a	R. solani^b	S. sclerotiorum^b	P. capsici^b	C. gloeosporioides^b	F. oxysporum^b	F. graminearum^b	F. fujikuroi^b	P. aphanidermatum^b	B. cinerea^b	P. oryzae^b	MIR^c%
I-1	3.42	22.15±2.51	16.80±2.08	8.74±0.93	18.68±0.54	12.18±0.84	45.05±0.79	25.77±2.43	17.37±1.24	28.14±1.89	50.10±2.15	24.5
I-2	3.84	35.64±2.64	29.23±1.98	26.81±0.73	33.50±0.36	26.98±0.42	53.91±1.42	37.99±3.02	31.75±0.35	45.08±1.92	44.66±1.31	36.56
I-3	4.25	57.46±1.06	41.00±0.60	55.71±0.20	43.34±0.74	36.92±0.56	57.43±0.34	38.22±2.22	33.88±1.22	63.22±2.16	49.28±2.33	47.65
I-4	4.17	60.46±0.43	32.10±1.71	44.76±0.35	43.69±0.41	39.11±2.22	57.31±1.42	51.48±1.40	39.77±0.54	45.65±0.52	36.10±0.57	45.04
I-5	5.09	57.57±1.19	43.62±2.67	60.49±0.93	44.64±1.03	41.41±0.63	61.85±1.23	48.02±0.87	42.48±0.41	84.41±2.03	57.84±3.18	54.23
I-6	4.64	63.82±0.87	48.85±0.45	57.23±0.88	44.40±2.05	47.72±0.21	62.76±1.04	55.74±0.69	46.72±0.41	58.42±1.04	21.61±0.29	50.73
I-7	5.05	65.79±2.81	50.16±0.78	57.69±0.35	48.91±0.21	45.05±1.31	76.61±2.39	55.86±0.87	49.08±1.41	68.36±1.04	26.22±3.21	54.37
I-8	3.49	18.75±3.79	17.19±1.18	21.45±0.81	25.56±0.54	20.18±0.42	39.03±1.48	37.76±3.99	33.40±2.84	47.12±2.06	75.46±0.29	33.59
I-9	3.09	3.18±2.74	0.31±0.78	2.80±0.70	12.40±0.54	8.90±0.56	37.78±0.39	33.15±1.60	33.52±1.22	44.18±2.07	34.29±0.49	21.05
I-10	3.76	21.82±2.19	23.99±1.77	31.24±0.88	32.08±0.71	23.70±1.52	42.55±0.39	45.37±1.20	35.29±1.06	39.44±1.41	78.26±0.99	37.37
I-11	4.92	60.20±0.87	54.87±2.08	59.91±1.41	50.57±0.62	37.41±0.36	55.95±0.79	46.52±1.06	53.32±0.61	86.78±3.11	41.04±0.57	54.66
I-12	4.61	64.80±1.51	67.03±0.39	53.15±1.95	53.77±0.36	43.84±0.21	75.25±0.52	51.48±0.20	77.84±0.82	88.25±0.85	82.54±1.03	65.8
I-13	2.80	15.90±1.55	7.12±0.23	0.00	12.87±0.36	8.18±0.21	31.77±0.20	21.39±2.22	15.37±0.41	58.87±3.20	29.02±1.24	20.05
I-14	3.91	26.75±4.06	25.95±0.23	21.45±0.53	31.96±0.21	21.88±1.83	56.18±0.39	30.61±3.73	21.97±0.74	18.42±0.39	51.91±0.57	30.71
I-15	3.91	19.19±2.33	17.32±2.61	18.88±1.05	21.76±0.62	19.46±0.42	31.77±1.29	25.54±3.81	15.49±0.61	55.14±1.09	38.24±1.71	26.28
I-16	3.91	3.29±2.37	8.69±0.82	16.90±1.58	20.46±0.21	15.21±7.31	35.51±1.42	16.55±2.69	12.78±1.14	38.64±1.55	46.64±0.99	21.47
I-17	4.29	52.96±3.47	44.40±0.82	50.70±1.26	39.90±0.62	36.44±1.11	48.23±1.77	48.48±2.42	27.39±0.74	52.09±2.18	28.19±3.02	42.88
I-18	4.64	54.82±1.52	49.63±2.16	53.73±0.73	44.64±1.03	35.10±0.42	49.25±0.59	42.95±1.38	46.49±1.08	66.10±1.89	27.54±1.51	47.03
I-19	5.34	68.75±0.33	65.72±1.59	59.91±1.07	40.61±1.23	61.67±0.76	68.44±1.94	59.77±0.53	48.14±1.47	73.79±2.74	24.74±2.00	57.15
I-20	4.64	41.34±1.55	24.65±0.78	39.42±1.15	28.99±0.21	25.16±1.38	48.00±1.71	31.77±2.22	29.40±0.20	47.29±0.24	23.09±2.00	33.91
I-21	5.63	65.24±1.33	72.53±1.04	45.34±1.41	46.42±0.21	31.59±1.67	70.59±0.20	42.25±0.35	32.11±2.55	88.93±0.39	43.02±0.57	53.8
I-22	3.07	48.03±3.01	0.00	24.94±1.01	33.14±1.23	12.54±2.00	56.18±0.39	34.65±1.04	18.79±2.13	0.00	74.80±1.31	30.31
I-23	4.28	66.01±1.00	11.43±0.45	87.18±0.73	52.11±0.54	28.68±1.89	79.11±2.58	52.51±1.00	84.21±0.82	49.04±3.43	53.15±2.45	56.34
I-24	3.55	40.24±2.64	1.88±0.78	34.73±2.27	40.02±0.21	16.06±0.76	61.06±0.52	55.62±0.53	8.06±0.71	6.67±0.85	71.34±1.48	33.57
Bifonazole	4.69	75.44±4.49	90.71±1.59	96.39±1.58	94.90±0.21	91.51±1.17	92.28±0.86	80.06±0.20	72.87±0.38	100.00	100.00	89.42

Compd.		Inhibition rate/(%, 50 mg/L)										MIR^c%
Compd.	Log P^a	R. solani^b	S. sclerotiorum^b	P. capsici^b	C. gloeosporioides^b	F. oxysporum^b	F. graminearum^b	F. fujikuroi^b	P. aphanidermatum^b	B. cinerea^b	P. oryzae^b	MIR^c%
I-1	3.42	22.15±2.51	16.80±2.08	8.74±0.93	18.68±0.54	12.18±0.84	45.05±0.79	25.77±2.43	17.37±1.24	28.14±1.89	50.10±2.15	24.5
I-2	3.84	35.64±2.64	29.23±1.98	26.81±0.73	33.50±0.36	26.98±0.42	53.91±1.42	37.99±3.02	31.75±0.35	45.08±1.92	44.66±1.31	36.56
I-3	4.25	57.46±1.06	41.00±0.60	55.71±0.20	43.34±0.74	36.92±0.56	57.43±0.34	38.22±2.22	33.88±1.22	63.22±2.16	49.28±2.33	47.65
I-4	4.17	60.46±0.43	32.10±1.71	44.76±0.35	43.69±0.41	39.11±2.22	57.31±1.42	51.48±1.40	39.77±0.54	45.65±0.52	36.10±0.57	45.04
I-5	5.09	57.57±1.19	43.62±2.67	60.49±0.93	44.64±1.03	41.41±0.63	61.85±1.23	48.02±0.87	42.48±0.41	84.41±2.03	57.84±3.18	54.23
I-6	4.64	63.82±0.87	48.85±0.45	57.23±0.88	44.40±2.05	47.72±0.21	62.76±1.04	55.74±0.69	46.72±0.41	58.42±1.04	21.61±0.29	50.73
I-7	5.05	65.79±2.81	50.16±0.78	57.69±0.35	48.91±0.21	45.05±1.31	76.61±2.39	55.86±0.87	49.08±1.41	68.36±1.04	26.22±3.21	54.37
I-8	3.49	18.75±3.79	17.19±1.18	21.45±0.81	25.56±0.54	20.18±0.42	39.03±1.48	37.76±3.99	33.40±2.84	47.12±2.06	75.46±0.29	33.59
I-9	3.09	3.18±2.74	0.31±0.78	2.80±0.70	12.40±0.54	8.90±0.56	37.78±0.39	33.15±1.60	33.52±1.22	44.18±2.07	34.29±0.49	21.05
I-10	3.76	21.82±2.19	23.99±1.77	31.24±0.88	32.08±0.71	23.70±1.52	42.55±0.39	45.37±1.20	35.29±1.06	39.44±1.41	78.26±0.99	37.37
I-11	4.92	60.20±0.87	54.87±2.08	59.91±1.41	50.57±0.62	37.41±0.36	55.95±0.79	46.52±1.06	53.32±0.61	86.78±3.11	41.04±0.57	54.66
I-12	4.61	64.80±1.51	67.03±0.39	53.15±1.95	53.77±0.36	43.84±0.21	75.25±0.52	51.48±0.20	77.84±0.82	88.25±0.85	82.54±1.03	65.8
I-13	2.80	15.90±1.55	7.12±0.23	0.00	12.87±0.36	8.18±0.21	31.77±0.20	21.39±2.22	15.37±0.41	58.87±3.20	29.02±1.24	20.05
I-14	3.91	26.75±4.06	25.95±0.23	21.45±0.53	31.96±0.21	21.88±1.83	56.18±0.39	30.61±3.73	21.97±0.74	18.42±0.39	51.91±0.57	30.71
I-15	3.91	19.19±2.33	17.32±2.61	18.88±1.05	21.76±0.62	19.46±0.42	31.77±1.29	25.54±3.81	15.49±0.61	55.14±1.09	38.24±1.71	26.28
I-16	3.91	3.29±2.37	8.69±0.82	16.90±1.58	20.46±0.21	15.21±7.31	35.51±1.42	16.55±2.69	12.78±1.14	38.64±1.55	46.64±0.99	21.47
I-17	4.29	52.96±3.47	44.40±0.82	50.70±1.26	39.90±0.62	36.44±1.11	48.23±1.77	48.48±2.42	27.39±0.74	52.09±2.18	28.19±3.02	42.88
I-18	4.64	54.82±1.52	49.63±2.16	53.73±0.73	44.64±1.03	35.10±0.42	49.25±0.59	42.95±1.38	46.49±1.08	66.10±1.89	27.54±1.51	47.03
I-19	5.34	68.75±0.33	65.72±1.59	59.91±1.07	40.61±1.23	61.67±0.76	68.44±1.94	59.77±0.53	48.14±1.47	73.79±2.74	24.74±2.00	57.15
I-20	4.64	41.34±1.55	24.65±0.78	39.42±1.15	28.99±0.21	25.16±1.38	48.00±1.71	31.77±2.22	29.40±0.20	47.29±0.24	23.09±2.00	33.91
I-21	5.63	65.24±1.33	72.53±1.04	45.34±1.41	46.42±0.21	31.59±1.67	70.59±0.20	42.25±0.35	32.11±2.55	88.93±0.39	43.02±0.57	53.8
I-22	3.07	48.03±3.01	0.00	24.94±1.01	33.14±1.23	12.54±2.00	56.18±0.39	34.65±1.04	18.79±2.13	0.00	74.80±1.31	30.31
I-23	4.28	66.01±1.00	11.43±0.45	87.18±0.73	52.11±0.54	28.68±1.89	79.11±2.58	52.51±1.00	84.21±0.82	49.04±3.43	53.15±2.45	56.34
I-24	3.55	40.24±2.64	1.88±0.78	34.73±2.27	40.02±0.21	16.06±0.76	61.06±0.52	55.62±0.53	8.06±0.71	6.67±0.85	71.34±1.48	33.57
Bifonazole	4.69	75.44±4.49	90.71±1.59	96.39±1.58	94.90±0.21	91.51±1.17	92.28±0.86	80.06±0.20	72.87±0.38	100.00	100.00	89.42

	Compd.	EC₅₀	Regression equation	R²	95% confidence interval
P. oryzae	I-08	49.17	y=－2.54＋1.48x	0.941	38.18~70.10
	I-10	33.34	y=－2.21＋1.44x	0.984	26.81~43.90
	I-12	15.67	y=－1.91＋1.59x	0.985	13.20~18.93
	I-22	46.03	y=－2.4＋1.45x	0.960	35.31~65.86
	I-24	20.77	y=－1.75＋1.33x	0.997	16.87~26.60
	Bifonazole	1.41	y=－0.21＋1.49x	0.947	0.72~2.12
B. cinerea	I-05	15.25	y=－1.97＋1.66x	0.992	12.94~18.24
	I-11	14.21	y=－1.4＋1.21x	0.985	11.41~17.92
	I-12	21.65	y=－2.09＋1.56x	0.970	18.15~26.57
	I-19	22.01	y=－1.82＋1.35x	0.992	17.92~28.13
	I-21	16.41	y=－1.85＋1.51x	0.982	13.72~20.02
	Bifonazole	1.78	y=－0.38＋1.41x	0.997	0.75~3.00
F. graminearum	I-07	22.84	y=－1.21＋0.89x	0.988	16.88~34.18
	I-12	17.3	y=－1.15＋0.93x	0.996	13.20~24.12
	I-21	19.71	y=－0.76＋0.59x	0.996	12.97~36.65
	I-23	12.76	y=－0.78＋0.71x	0.991	9.12~18.98
	Bifonazole	0.1	y=0.76＋0.77x	0.920	0.08~0.15
P. aphanidermatum	I-12	27.54	y=－2.68＋1.86x	0.976	23.41~33.34
	I-23	14.03	y=－2.73＋2.35x	0.963	9.87~20.48
	Bifonazole	14.87	y=－1.97＋1.66x	0.996	10.94~21.28
P. capsici	I-23	20.17	y=－3.95＋3.02x	0.997	18.07~22.62
P. capsici	Bifonazole	6.5	y=－2.59＋3.11x	0.985	5.83~7.23
S. sclerotiorum	I-21	16.53	y=－1.93＋1.57x	0.963	14.00~19.86
S. sclerotiorum	Bifonazole	11.94	y=－2.01＋1.89x	0.984	10.36~13.84

	Compd.	EC₅₀	Regression equation	R²	95% confidence interval
P. oryzae	I-08	49.17	y=－2.54＋1.48x	0.941	38.18~70.10
	I-10	33.34	y=－2.21＋1.44x	0.984	26.81~43.90
	I-12	15.67	y=－1.91＋1.59x	0.985	13.20~18.93
	I-22	46.03	y=－2.4＋1.45x	0.960	35.31~65.86
	I-24	20.77	y=－1.75＋1.33x	0.997	16.87~26.60
	Bifonazole	1.41	y=－0.21＋1.49x	0.947	0.72~2.12
B. cinerea	I-05	15.25	y=－1.97＋1.66x	0.992	12.94~18.24
	I-11	14.21	y=－1.4＋1.21x	0.985	11.41~17.92
	I-12	21.65	y=－2.09＋1.56x	0.970	18.15~26.57
	I-19	22.01	y=－1.82＋1.35x	0.992	17.92~28.13
	I-21	16.41	y=－1.85＋1.51x	0.982	13.72~20.02
	Bifonazole	1.78	y=－0.38＋1.41x	0.997	0.75~3.00
F. graminearum	I-07	22.84	y=－1.21＋0.89x	0.988	16.88~34.18
	I-12	17.3	y=－1.15＋0.93x	0.996	13.20~24.12
	I-21	19.71	y=－0.76＋0.59x	0.996	12.97~36.65
	I-23	12.76	y=－0.78＋0.71x	0.991	9.12~18.98
	Bifonazole	0.1	y=0.76＋0.77x	0.920	0.08~0.15
P. aphanidermatum	I-12	27.54	y=－2.68＋1.86x	0.976	23.41~33.34
	I-23	14.03	y=－2.73＋2.35x	0.963	9.87~20.48
	Bifonazole	14.87	y=－1.97＋1.66x	0.996	10.94~21.28
P. capsici	I-23	20.17	y=－3.95＋3.02x	0.997	18.07~22.62
P. capsici	Bifonazole	6.5	y=－2.59＋3.11x	0.985	5.83~7.23
S. sclerotiorum	I-21	16.53	y=－1.93＋1.57x	0.963	14.00~19.86
S. sclerotiorum	Bifonazole	11.94	y=－2.01＋1.89x	0.984	10.36~13.84