Synthesis, Crystal Structure and Herbicide Activity of Three Phenyl-naphthyl Methanone Derivatives  

作　　者：FU Ying ZHANG Shuai-Qi HAN Zhi-Bo WANG Kui KANG Jing-Xin YE Fei 付颖;张帅琦;韩志波;王奎;康晶欣;叶非(College of Science,Northeast Agricultural University,Harbin 150030,China;Daqing Chemical Research Center of Petrochemical Research Institute,China Petroleum,Daqing 163714,China)

机构地区：[1]College of Science,Northeast Agricultural University,Harbin 150030,China [2]Daqing Chemical Research Center of Petrochemical Research Institute,China Petroleum,Daqing 163714,China

出　　处：《Chinese Journal of Structural Chemistry》2019年第11期1881-1888,共8页结构化学（英文）

基　　金：supported by the National Natural Science Foundation of China(No.31772208);Natural Science Foundation of Heilongjiang Province(No.ZD2017002);the Research Science Foundation in Technology Innovation of Harbin(No.2017RAQXJ0172)

摘　　要：Three phenyl-naphthyl methanone derivatives have been designed and synthesized through alkylation and Friedel-Crafts acylation reactions.All the compounds were characterized by IR,1H NMR,13C NMR and H RMS.The single crystal structure of the compounds has been further determined by X-ray diffraction.(4-Ethoxynaphthalen-1-yl)(2-methylphenyl)methanone(3a)crystallizes in monoclinic system,P21/c space group with a=13.144(3),b=11.041(2),c=11.320(2)?,β=106.65(3)°,V=1573.7(5)?3,Dc=1.225 Mg/m3,Z=4,F(000)=616,μ(MoKα)=0.078 mm-1,R=0.0928 and wR=0.1556.(4-Ethoxynaphthalen-1-yl)(2-hydroxyphenyl)methanone(3b)belongs to the monoclinic system,P21/c space group with a=9.985(2),b=10.814(2),c=14.353(3)?,β=105.49(3)°,V=1493.6(5)?3,Dc=1.300 Mg/m3,Z=4,F(000)=616,μ(MoKα)=0.087 mm-1,R=0.0568 and wR=0.1262.(4-Methoxynaphthalen-1-yl)(4-methylphenyl)methanone(3c)crystallizes in monoclinic system,P21/c space group with a=7.6130(15),b=15.068(3),c=12.880(3)?,β=100.63(3)°,V=1452.1(5)?3,Dc=1.264 Mg/m3,Z=4,F(000)=584,μ(MoKα)=0.081 mm-1,R=0.0804 and wR=0.1349.The presence of van der Waals forces leads to the stability of the compounds.Especially,compounds 3a^c showed herbicidal activity against the monocotyledon plant barnyard grass(Echinochloa crus-galli).At the concentration of 0.75 mmol/m^2,compound 3b(Ct=0.436±0.116 mg/g)exhibited better activity than pyrazoxyfen(Ct=0.537±0.073 mg/g).

关 键 词：phenyl-naphthyl methanone SYNTHESIS single crystal structure bioactivity 

分 类 号：O62[理学—有机化学]