Synthesis and Fungicidal Activity of Novel Allyl Benzoate Compounds Containing Triazole

doi:10.6023/cjoc202006037

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (2): 826-832.DOI: 10.6023/cjoc202006037 Previous Articles Next Articles

NOTE

新型含三唑的烯丙基苯甲酸酯类化合物的合成及杀菌活性研究

余玮^a, 王翰^a, 闵莉静^b, 华学文^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院浙江湖州 313000
c 聊城大学农学院山东聊城 252000

收稿日期:2020-06-19 修回日期:2020-07-20 发布日期:2020-10-22
通讯作者: 刘幸海
作者简介:
* Corresponding author. E-mail: xhliu@zjut.edu.cn
基金资助:
浙江省自然科学基金(LY19C140002); 浙江省教育厅(Y201941832)

Synthesis and Fungicidal Activity of Novel Allyl Benzoate Compounds Containing Triazole

Wei Yu^a, Han Wang^a, Li-Jing Min^b, Xue-Wen Hua^c, Xing-Hai 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 Agriculture, Liaocheng University, Liaocheng, Shandong 252000

Received:2020-06-19 Revised:2020-07-20 Published:2020-10-22
Contact: Xing-Hai Liu
Supported by:
the Natural Science Foundation of Zhejiang Province(LY19C140002); the Research Fund of Department of Education of Zhejiang Province(Y201941832)

1. cjoc202006037辅助材料.pdf(1578KB)

Abstract

In order to find pesticide lead compounds with high fungicidal activity, a series of unreported allyl benzoate compounds containing triazole were designed and synthesized. The structures were confirmed by ¹H NMR and HRMS, and the crystal structure of (R,S)-(Z)-1,3-diphenyl-2-(1H-1,2,4-triazol-1-yl)allyl 2,3-dichlorobenzoate (5j) was determined by X-ray single crystal diffraction. The bioassay results showed that (R,S)-(Z)-1,3-diphenyl-2-(1H-1,2,4-triazol-1-yl)allyl benzoate (5a), (R,S)-(Z)-1,3-diphenyl-2-(1H-1,2,4-triazol-1-yl)allyl 2-fluorobenzoate (5g) and (R,S)-(Z)-1,3-diphenyl-2-(1H-1,2,4-triazol-1- yl)allyl 3-methylbenzoate (5n) exhibited good control efficacy against Sclerotinia sclerotiorummore than 70% at 50 mg/L.

Key words: triazole fungicide, synthesis, fungicidal activity, structure activity relationship (SAR)

Cite this article

Wei Yu, Han Wang, Li-Jing Min, Xue-Wen Hua, Xing-Hai Liu. Synthesis and Fungicidal Activity of Novel Allyl Benzoate Compounds Containing Triazole[J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 826-832.

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化合物	Alternari asolani	Gibberella zeae	Phytophthora infestans	Phytophthora capsici	Sclerotinia sclerotiorum	Botrytis cinerea	Rhizoctonia solani	Fusarium oxysporum	Cercospora arachidicola	Physalospora piricola
5a	7.7	39.1	12.5	14.3	71.4	23.8	50.0	4.5	25.0	25.0
5b	15.4	30.4	12.5	14.3	69.6	14.3	57.1	18.2	16.7	16.7
5c	7.7	34.8	6.3	7.1	67.9	28.6	31.0	18.2	8.3	8.3
5d	7.7	17.4	12.5	7.1	60.7	9.5	50.0	4.5	8.3	25.0
5e	23.1	26.1	6.3	7.1	60.7	23.8	57.1	4.5	8.3	8.3
5f	15.4	13.0	18.8	32.1	39.3	4.8	23.8	4.5	8.3	50.0
5g	15.4	43.5	12.5	17.9	71.4	23.8	54.8	18.2	16.7	58.3
5h	15.4	34.8	18.8	32.1	62.5	28.6	61.9	27.3	50.0	16.7
5i	7.7	30.4	18.8	17.9	60.7	19.0	50.0	4.5	16.7	50.0
5j	11.5	17.4	25.0	7.1	35.7	9.5	14.3	9.1	8.3	58.3
5k	7.7	8.7	25.0	7.1	35.7	19.0	23.8	4.5	16.7	25.0
5l	15.4	17.4	18.8	7.1	17.9	9.5	57.1	4.5	8.3	8.3
5m	7.7	30.4	25.0	10.7	67.9	28.6	61.9	9.1	16.7	58.3
5n	7.7	30.4	28.1	25.0	71.4	28.6	54.8	9.1	16.7	16.7
5o	30.8	34.8	12.5	25.0	69.6	28.6	57.1	9.1	8.3	50.0
5p	15.4	30.4	18.8	25.0	48.2	23.8	54.8	13.6	8.3	58.3
清水	0	0	0	0	0	0	0	0	0	0
氟唑菌酰胺	88.9	30.3	29.7	38.1	96.4	63.6	88.4	44.4	100	84.6

化合物	Alternari asolani	Gibberella zeae	Phytophthora infestans	Phytophthora capsici	Sclerotinia sclerotiorum	Botrytis cinerea	Rhizoctonia solani	Fusarium oxysporum	Cercospora arachidicola	Physalospora piricola
5a	7.7	39.1	12.5	14.3	71.4	23.8	50.0	4.5	25.0	25.0
5b	15.4	30.4	12.5	14.3	69.6	14.3	57.1	18.2	16.7	16.7
5c	7.7	34.8	6.3	7.1	67.9	28.6	31.0	18.2	8.3	8.3
5d	7.7	17.4	12.5	7.1	60.7	9.5	50.0	4.5	8.3	25.0
5e	23.1	26.1	6.3	7.1	60.7	23.8	57.1	4.5	8.3	8.3
5f	15.4	13.0	18.8	32.1	39.3	4.8	23.8	4.5	8.3	50.0
5g	15.4	43.5	12.5	17.9	71.4	23.8	54.8	18.2	16.7	58.3
5h	15.4	34.8	18.8	32.1	62.5	28.6	61.9	27.3	50.0	16.7
5i	7.7	30.4	18.8	17.9	60.7	19.0	50.0	4.5	16.7	50.0
5j	11.5	17.4	25.0	7.1	35.7	9.5	14.3	9.1	8.3	58.3
5k	7.7	8.7	25.0	7.1	35.7	19.0	23.8	4.5	16.7	25.0
5l	15.4	17.4	18.8	7.1	17.9	9.5	57.1	4.5	8.3	8.3
5m	7.7	30.4	25.0	10.7	67.9	28.6	61.9	9.1	16.7	58.3
5n	7.7	30.4	28.1	25.0	71.4	28.6	54.8	9.1	16.7	16.7
5o	30.8	34.8	12.5	25.0	69.6	28.6	57.1	9.1	8.3	50.0
5p	15.4	30.4	18.8	25.0	48.2	23.8	54.8	13.6	8.3	58.3
清水	0	0	0	0	0	0	0	0	0	0
氟唑菌酰胺	88.9	30.3	29.7	38.1	96.4	63.6	88.4	44.4	100	84.6

新型含三唑的烯丙基苯甲酸酯类化合物的合成及杀菌活性研究

Synthesis and Fungicidal Activity of Novel Allyl Benzoate Compounds Containing Triazole

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