Synthesis and Insecticidal Activity of 3-Ethyl Sulfone Pyridine Substituted Aryl Triazole Compounds

doi:10.6023/cjoc202009042

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (5): 2055-2062.DOI: 10.6023/cjoc202009042 Previous Articles Next Articles

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含芳基三氮唑结构的3-乙砜基吡啶类化合物的合成及杀虫活性研究

姚阳意^a, 任朝丽^a, 陈丽^a, 钟良坤^a^,^b, 许天明^b^,^*(), 谭成侠^a^,^*()

a 浙江工业大学化学工程学院杭州 310014
b 浙江省化工研究院有限公司杭州 310023

收稿日期:2020-09-18 修回日期:2020-12-14 发布日期:2021-02-22
通讯作者: 许天明, 谭成侠
基金资助:
2011绿色农药协同创新中心(KYY-ZX-20170007)

Synthesis and Insecticidal Activity of 3-Ethyl Sulfone Pyridine Substituted Aryl Triazole Compounds

Yangyi Yao^a, Chaoli Ren^a, Li Chen^a, Liangkun Zhong^a^,^b, Tianming Xu^b^,^*(), Chengxia Tan^a^,^*()

a College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014
b Zhejiang Research Institute of Chemical Industry. Ltd., Hangzhou 310023

Received:2020-09-18 Revised:2020-12-14 Published:2021-02-22
Contact: Tianming Xu, Chengxia Tan
About author:
* Corresponding authors. E-mail: tanchengxia@zjut.edu.cn;
E-mail: 916312357@qq.com
Supported by:
Collaborative Innovation Center of 2011 Green Pesticide(KYY-ZX-20170007)

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Abstract

According to the principle of active substructure splicing, novel 3-ethyl sulfone pyridine substituted aryl triazole compounds were designed and synthesized using 3,6-dichloropyridine-2-carboxylic acid as primary material. All the compounds were characterized by ¹H NMR, ¹³C NMR and HRMS spectra. The preliminary bioassay indicated that most title compounds exhibited relatively high insecticidal activity against Mythimna separata walker at 500 mg/L. Especially 2-(3-(2,6-difluorophenyl)-1-methyl-1H-1,2,4-triazol-5-yl)-3-(ethylsulfonyl)-6-(pyrrolidin-1-yl)pyridine (9c), N-(sec-butyl)-6- (3-(2,6-difluorophenyl)-1-methyl-1H-1,2,4-triazol-5-yl)-5-(ethylsulfonyl)pyridin-2-amine (9g), 6-(3-(2,6-difluorophenyl)-1- methyl-1H-1,2,4-triazol-5-yl)-5-(ethylsulfonyl)-N-isobutylpyridin-2-amine (9h) exhibited mortality 80% against M. separate at 100 mg/L.

Key words: ethylsulfone, triazole, pyridine, synthesis, insecticidal activity

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Yangyi Yao, Chaoli Ren, Li Chen, Liangkun Zhong, Tianming Xu, Chengxia Tan. Synthesis and Insecticidal Activity of 3-Ethyl Sulfone Pyridine Substituted Aryl Triazole Compounds[J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 2055-2062.

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Fig. & Tab. 3

Scheme 1. Design strategy of the target compounds

Scheme 2. Synthetic routes of the target compounds 9a~9o 9a: R=3-(trifluoromethyl)-1H-pyrazolyl, 9b: R=1H-1,2,4-triazolyl, 9c: R=1H-pyrrolidinyl, 9d: R=NHC2H5, 9e: R=NH(CH2)2CH3, 9f: R=NH(CH2)3CH3, 9g: R=NHCH(CH3)CH2CH3, 9h: R=NHCH2CH(CH3)2, 9i: R=1H-cyclopentanaminyl, 9j: R=NHCH3, 9k: R=5-(2,6-difluoro- phenyl)-1H-1,2,4-triazolyl, 9l: R=3-(4-chlorophenyl)-1H-1,2,4-triazolyl, 9m: R=3-(3-chlorophenyl)-1H-1,2,4-triazolyl, 9n: R=3-(3-fluoro- phenyl)-1H-1,2,4-triazolyl, 9o: R=3-(2-chlorophenyl)-1H-1,2,4-triazolyl

Compd.	R	Mortality/%
Compd.	R	500 mg/L	100 mg/L
9a		100	0
9b		70	0
9c		100	80
9d	—NHC₂H₅	80	50
9e	—NH(CH₂)₂CH₃	100	0
9f	—NH(CH₂)₃CH₃	80	30
9g	—NHCH(CH₃)CH₂CH₃	100	80
9h	—NHCH₂CH(CH₃)₂	100	80
9i		90	0
9j	—NHCH₃	100	50
9k		80	0
9l		80	0
9m		80	0
9n		80	0
9o		80	0
Avermectin	—	100	100
CK^a	—	0	0

Table 1. Insecticidal activities (mortality/%) of of title compounds against Mythimna. separata walker

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含芳基三氮唑结构的3-乙砜基吡啶类化合物的合成及杀虫活性研究

Synthesis and Insecticidal Activity of 3-Ethyl Sulfone Pyridine Substituted Aryl Triazole Compounds

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