Synthesis, Cyrstal Structure and Fungicidal Activity of New Triazole Compounds Containing Trifluoromethylphenyl Moiety

doi:10.6023/cjoc202106025

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (11): 4498-4503.DOI: 10.6023/cjoc202106025 Previous Articles Next Articles

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含三氟甲基苯基的三唑化合物的合成、晶体结构及杀菌活性研究

余陈升^a, 王翰^a, 闵莉静^b, 韩亮^a, 史建俊^c^,^*(), 刘幸海^a^,^*()

a 浙江工业大学化学工程学院杭州 310014
b 湖州师范学院生命科学学院浙江省媒介生物学与病原控制重点实验室浙江湖州 313000
c 黄山学院化学化工学院安徽黄山 245041

收稿日期:2021-06-11 修回日期:2021-07-09 发布日期:2021-07-26
通讯作者: 史建俊, 刘幸海
基金资助:
浙江省自然科学基金(LY19C140002); 浙江省自然科学基金(LY19B020009); 浙江三赢新材料有限公司(KYY-HX-20200746)

Synthesis, Cyrstal Structure and Fungicidal Activity of New Triazole Compounds Containing Trifluoromethylphenyl Moiety

Chensheng Yu^a, Han Wang^a, Lijing Min^b, Liang Han^a, Jianjun Shi^c(), Xinghai Liu^a()

a College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014
b Key Laboratory of Vector Biology and Pathogen Control of Zhejiang Province, College of Life Science, Huzhou University, Huzhou, Zhejiang 313000
c College of Chemistry & Chemical Engineering, Huangshan University, Huangshan, Anhui 245041

Received:2021-06-11 Revised:2021-07-09 Published:2021-07-26
Contact: Jianjun Shi, Xinghai Liu
Supported by:
Zhejiang Provincial Natural Science Foundation(LY19C140002); Zhejiang Provincial Natural Science Foundation(LY19B020009); Three Win Material Company(KYY-HX-20200746)

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Abstract

In order to find new lead compounds with high activity, a series of 1,2,4-triazole compounds were designed and synthesized by using Uniconazole as temple compound. Their structures were confirmed by ¹H NMR, ¹³C NMR and HRMS spectra, and the crystal structure of (E)-1-phenyl-2-(1H-1,2,4-triazol-1-yl)-3-(4-(trifluoromethyl)phenyl)allyl-benzoate (5a) was determined by X-ray single crystal diffraction. The bioassay data showed that some of target compounds 5 exhibited good activity (>50%) against Sclerotinia sclerotiorum and Rhizoctonia solanimore at 50 μg/mL.

Key words: synthesis, crystal structure, triazole fungicides, molecular docking

Cite this article

Chensheng Yu, Han Wang, Lijing Min, Liang Han, Jianjun Shi, Xinghai Liu. Synthesis, Cyrstal Structure and Fungicidal Activity of New Triazole Compounds Containing Trifluoromethylphenyl Moiety[J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4498-4503.

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Fig. & Tab. 5

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Compd.	AS	GZ	PI	PC	SS	BC	RS	FO	CA	PP
5a	15.4	30.4	25.0	42.9	53.6	33.3	54.8	13.6	8.3	8.3
5b	7.7	30.4	31.3	39.3	62.5	9.5	42.9	4.5	16.7	8.3
5c	11.5	30.4	25.0	42.9	67.9	33.3	50.0	4.5	8.3	8.3
5d	11.5	8.7	12.5	25.0	26.8	33.3	31.0	9.1	8.3	8.3
5e	7.7	17.4	6.3	25.0	53.6	23.8	38.1	4.5	16.7	25.0
5f	15.4	17.4	6.3	32.1	53.6	38.1	50.0	9.1	25.0	33.3
5g	38.5	52.2	18.8	39.3	58.9	38.1	66.7	4.5	25.0	33.3
5h	23.1	17.4	12.5	25.0	50.0	33.3	38.1	4.5	16.7	8.3
5i	23.1	21.7	12.5	35.7	57.1	33.3	38.1	13.6	25.0	8.3
5j	11.5	8.7	25.0	35.7	35.7	23.8	14.3	13.6	8.3	8.3
CK	0	0	0	0	0	0	0	0	0	0
Fluxapyroxad	88.9	28.6	27.3	16.7	96.4	63.6	88.4	100	44.4	84.6

Compd.	AS	GZ	PI	PC	SS	BC	RS	FO	CA	PP
5a	15.4	30.4	25.0	42.9	53.6	33.3	54.8	13.6	8.3	8.3
5b	7.7	30.4	31.3	39.3	62.5	9.5	42.9	4.5	16.7	8.3
5c	11.5	30.4	25.0	42.9	67.9	33.3	50.0	4.5	8.3	8.3
5d	11.5	8.7	12.5	25.0	26.8	33.3	31.0	9.1	8.3	8.3
5e	7.7	17.4	6.3	25.0	53.6	23.8	38.1	4.5	16.7	25.0
5f	15.4	17.4	6.3	32.1	53.6	38.1	50.0	9.1	25.0	33.3
5g	38.5	52.2	18.8	39.3	58.9	38.1	66.7	4.5	25.0	33.3
5h	23.1	17.4	12.5	25.0	50.0	33.3	38.1	4.5	16.7	8.3
5i	23.1	21.7	12.5	35.7	57.1	33.3	38.1	13.6	25.0	8.3
5j	11.5	8.7	25.0	35.7	35.7	23.8	14.3	13.6	8.3	8.3
CK	0	0	0	0	0	0	0	0	0	0
Fluxapyroxad	88.9	28.6	27.3	16.7	96.4	63.6	88.4	100	44.4	84.6

含三氟甲基苯基的三唑化合物的合成、晶体结构及杀菌活性研究

Synthesis, Cyrstal Structure and Fungicidal Activity of New Triazole Compounds Containing Trifluoromethylphenyl Moiety

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