Microwave-assistant Syntheses, Crystal Structures and Safener Activities of Two Substituted Phenyl Isoxazole Derivatives  

作　　者：GAO Ying-Chao SHAO Xin-Xin FU Ying 高颖超;邵鑫鑫;付颖(College of Arts and Sciences,Northeast Agricultural University,Harbin 150030,China)

机构地区：[1]College of Arts and Sciences,Northeast Agricultural University,Harbin 150030,China

出　　处：《Chinese Journal of Structural Chemistry》2021年第9期1231-1237,1111,共8页结构化学（英文）

基　　金：the National Natural Science Foundation of China(No.31801784 and 31572042);Undergraduate SIPT program of Northeast Agricultural University(No.202010224112)。

摘　　要：Two novel substituted phenyl isoxazole benzoxazine formamide derivatives were designed and synthesized with substituted o-aminophenol,1,2-dibromoethane and different phenyl substituted isoxazole formyl chloride as the raw materials via microwave assistant synthesis.The target compounds were characterized by IR,^(1)H NMR,^(13)C NMR and HRMS.Both single-crystal structures were further determined by X-ray diffraction.3-(2’-Chloro-6’-fluoro-phenyl)-4-(2’,3’-dihydro-1’,4’-benzoxazine)-5-methyl-isoxazole formamide (4a) crystallizes in orthorhombic system,P2_(1) space group with a=8.9414(18),b=10.834(2),c=17.706(4)A,V=1715.1(6)A^(3),D_(c)=1.444 Mg/m^(3),Z=4,F(000)=768,μ(Mo Kα)=0.255 mm^(-1),R=0.0406 and wR=0.1171.3-Phenyl-4-(6-methyl-2’,3’-dihydro-1’,4’-benzoxazine)-5-methyl-isoxazole formamide (4b) is of triclinic system,space group PI with a=7.7659(16),b=8.3626(17),c=13.484(3)A,α=76.04(3)°,β=100.63(3)°,γ=82.01(3)°,V=841.6(3)A^(3),D_(c)=1.319 Mg/m^(3),Z=2,F(000)=352,μ(Mo Kα)=0.090 mm^(-1),R=0.0672 and wR=0.2671.Both crystals are packed through C–H···O hydrogen bonding interaction.There is C–H···F hydrogen bond between 4a molecules,and C–H···N between 4b molecules.Bioassay results showed that compounds 4a and 4b exhibited detoxification on maize and restored maize growth index.

关 键 词：isoxazole benzoxazine formamide microwave-assistant synthesis single-crystal structure safener activity 

分 类 号：TQ457.2[化学工程—农药化工]