Synthesis and Fungicidal Activity of Novel 2-(Arylaminoethylamino)benzyl Alcohols

doi:10.11944/j.issn.1000-0518.20176.03.160236

Chinese Journal of Applied Chemistry ›› 2017, Vol. 34 ›› Issue (3): 345-353.DOI: 10.11944/j.issn.1000-0518.20176.03.160236

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Synthesis and Fungicidal Activity of Novel 2-(Arylaminoethylamino)benzyl Alcohols

TANG Zilong^a^b^*(),TAN Jingzhao^a,CAI Lanqiong^a,LI Xinxing^a,LIU Wanqiang^b

^aKey Laboratory of Theoretical Organic Chemistry and Functional Molecule,Ministry of Education,Hu'nan University of Science and Technology,Xiangtan,Hu'nan 411201,China
^bSchool of Chemistry and Chemical Engineering,Hu'nan University of Science and Technology,Xiangtan,Hu'nan 411201,China

Received:2016-06-06 Accepted:2016-09-18 Published:2017-02-27 Online:2017-02-27
Contact: TANG Zilong
Supported by:
Supported by the National Natural Science Foundation of China(No.201372070), the Subproject of National Key Technology R&D Program(No.2011BAE06B01), the Scientific Research Fund of Hu'nan Provincial Education Department(No.13K089), the Open Project of Key Laboratory of Theoretical Organic Chemistry and Functional Molecules of Ministry of Education(No.LKF1302)

Abstract

Abstract:

2-Aminobenzyl alcohol and its derivatives are a kind of important bifunctional compounds, and has found wide application in organic chemistry and drug synthesis. An efficient and simple method for synthesis of 2-(arylaminoethylamino)benzyl alcohols was described and the fungicidal activities of the target compounds were evaluated in this paper. N-alkylation of 2-aminobenzyl alcohol with bromoacetyl aryl amines produced 2-[(2-hydroxymethylphenyl)amino] acetyl aryl amines 3a~3i, which were reduced by LiAlH₄ giving a series of novel 2-(arylaminoethylamino)benzyl alcohols 5a~5i in 76%~95% yields. All the structures of the target compounds were characterized by the infrared spectroscopy(IR), proton nuclear magnetic resonance spectroscopy(¹H NMR), ¹³C NMR and elemental analysis. Most of compounds show moderate to good fungicidal activities under the testing concentration. Compound 5e shows 73% activity of against Phytophythora capsici.

Key words: (arylaminoethylamino)benzyl alcohol, alkylation, synthesis, fungicidal activity

TANG Zilong, TAN Jingzhao, CAI Lanqiong, LI Xinxing, LIU Wanqiang. Synthesis and Fungicidal Activity of Novel 2-(Arylaminoethylamino)benzyl Alcohols[J]. Chinese Journal of Applied Chemistry, 2017, 34(3): 345-353.

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Synthesis and Fungicidal Activity of Novel 2-(Arylaminoethylamino)benzyl Alcohols

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