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Citation: TANG Zilong, XIA Zanwen, MA Hongwei, LIU Hanwen, OU Xiaoming. Synthesis of 3,6(8) -Disubstituted-2,4-Dihydro-1,3 benzoxazines via Mannich Reaction and Their Fungicidal Activities[J]. Chinese Journal of Applied Chemistry, ;2013, 30(9): 993-998. doi: 10.3724/SP.J.1095.2013.20507 shu

Synthesis of 3,6(8) -Disubstituted-2,4-Dihydro-1,3 benzoxazines via Mannich Reaction and Their Fungicidal Activities

TANG Zilong ^a,b,c, ,
XIA Zanwen ^a ,
MA Hongwei ^a ,
LIU Hanwen ^a,b,c ,
OU Xiaoming ^b,d

a. School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201, China;
b. Key Laboratory of Theoretical Chemistry and Molecular Simulation of Ministry of Education, Hunan University of Science and Technology, Xiangtan 411201, China;
c. Hunan Provincial University, Key Laboratory of QSAR/QSPR Hunan University of Science and Technology, Xiangtan 411201, China;
d. National Engineering Research Center for Agrochemicals, Hunan Research Institute of Chemical Industry, Changsha 410014, China

Received Date: 6 November 2012
Revised Date: 15 January 2013

A series of novel 3,6(8)-disubstituted 2,4-dihydro-1,3-benzoxazines was synthesized by Mannich reactions of substituted anilines with paraformaldehyde and substituted phenols in the absence of catalyst. The results show that substituted phenols and anilines with electron-donating groups on the phenyl ring give higher yields than those with electron-withdrawing groups. The structures of the products were characterized by ¹H NMR,¹³C NMR,IR and MS. The fungicidal activity of the title compounds was preliminarily evaluated.Compounds 4j and 4d show 86.1% and 81.5% activity against Sclerotonia sclerotiorum at the concentration of 25 mg/L,respectively. Compound 4i exhibits 81.6% activity against Botrytis cinerea.
- disubstituted-dihydro-benzoxazines,
- synthesis,
- Mannich reaction,
- fungicidal activity
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