1-(水杨醛)-5-(香草醛)缩卡巴肼丁基锡配合物的合成、结构、谱学性质和除草活性
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摘要
卡巴肼分别与水杨醛和香草醛缩合制备1,5-不对称二取代卡巴肼配体,在甲醇溶剂热中,正丁基三氯化锡与配体反应,合成1-(水杨醛)-5-(香草醛)缩卡巴肼丁基锡配合物(B1)和含N,N′-双水杨醛缩连氮分子的丁基锡配合物(B2),经元素分析,IR,1H、119Sn、13C NMR和X射线衍射晶体结构表征,配合物(B1)、(B2)晶体分别属单斜晶系、P21/n空间群和三斜晶系、P1空间群,中心锡与配基原子构成六配位畸形八面体构型,配合物(B1)在DMF-H2O溶剂体系中具有良好的荧光性质,当含水0~10%(V/V)时具有聚集荧光增强效应,含水量大于10%,随含水体积分数增加荧光强度减弱,以至最后淬灭。配体及其配合物(B1)对马齿苋、刺苋、决明子、四九菜心和苋菜5种靶标植物均具有一定生长抑制作用,尤其是配体对马齿苋、刺苋的生长有良好的抑制作用,配合物可以选择性抑制决明子的生长,可作为决明子除草剂的候选化合物。
The 1,5-asymmetric disubstituted carbohydrazide ligands were prepared by condensation of carbohy-drazide with salicylaldehyde and then with vanillin. The butyltin complex B1 based on the 1,5-disubstituted carbohydrazide and the complex B2 containing salicylaldehyde azine were obtained by solvothermal reaction of nBuSnCl3 with the ligand in methanol environments, which have been structurally characterized by elemental analysis, IR and1 H,13 C,119 Sn NMR spectra. The crystal of complex B1 belongs to monoclinic system, space group P21/n, and the crystal of complex B2 belongs to triclinic system, space group P1. The Sn atom is six-coordinated with distorted octahedral geometry by O, N atoms from ligand, C atom of butyl and two Cl atoms. The complex B1 had good fluorescence properties in the DMF-H2 O solvents, and the water content in the 0~10%(V/V) range had aggregation induced emission enhancement(AIE). When the water content was more than 10%, the fluorescence intensity decreased with the increase of water volume fraction, and finally was quenched. The ligand and its butyltin complex B1 have the effect of growth on the target plants, such as Portulaca oleracea L.,Amaranthus spinosus L., Cassia tora L., Brassica campestris L. ssp. chinensis var. utilis Tsen et Lee and Amaranthus tricolor L. The ligand has a good inhibitory effect on the growth of Portulaca oleracea L. and Amaranthus spinosus L., and the complex has selective inhibition on the growth of Cassia tora L., which can be used as a candidate compound for Cassia tora L. herbicide. CCDC: 1511212, B1; 1845664, B2.
The 1,5-asymmetric disubstituted carbohydrazide ligands were prepared by condensation of carbohy-drazide with salicylaldehyde and then with vanillin. The butyltin complex B1 based on the 1,5-disubstituted carbohydrazide and the complex B2 containing salicylaldehyde azine were obtained by solvothermal reaction of nBuSnCl3 with the ligand in methanol environments, which have been structurally characterized by elemental analysis, IR and1 H,13 C,119 Sn NMR spectra. The crystal of complex B1 belongs to monoclinic system, space group P21/n, and the crystal of complex B2 belongs to triclinic system, space group P1. The Sn atom is six-coordinated with distorted octahedral geometry by O, N atoms from ligand, C atom of butyl and two Cl atoms. The complex B1 had good fluorescence properties in the DMF-H2 O solvents, and the water content in the 0~10%(V/V) range had aggregation induced emission enhancement(AIE). When the water content was more than 10%, the fluorescence intensity decreased with the increase of water volume fraction, and finally was quenched. The ligand and its butyltin complex B1 have the effect of growth on the target plants, such as Portulaca oleracea L.,Amaranthus spinosus L., Cassia tora L., Brassica campestris L. ssp. chinensis var. utilis Tsen et Lee and Amaranthus tricolor L. The ligand has a good inhibitory effect on the growth of Portulaca oleracea L. and Amaranthus spinosus L., and the complex has selective inhibition on the growth of Cassia tora L., which can be used as a candidate compound for Cassia tora L. herbicide. CCDC: 1511212, B1; 1845664, B2.
引文
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[4]Rubc姚ic'M,Galic'N,Halasz I,et al.Cryst.Growth.Des.,2014,14(6):2900-2912
[5]Sutradhar M,Barman T R,Rentschle E.Inorg.Chem.Commun.,2014,39:140-143
[6]ZHU Ji-Hua(朱继华),ZHENG Xu-Dong(郑旭东),GUO GuoZhe(郭国哲),et al.Chin.J.Org.Chem.(有机化学),2015,35(6):1975-1980
[7]YANG Chun-Lin(杨春林),FENG Yong-Lan(冯泳兰),ZHANGFu-Xing(张复兴),et al.Chinese J.Inorg.Chem.(无机化学学报),2017,33(8):1397-1402
[8]Tan S F,Ang K P,Jayachandran H.Transition Met.Chem.,1988,13:64-68
[9]Sheldrick G M.SHELXTL,Version 5.03,Madison,Wisconsin,USA,1994.
[10]FANG Xiao-Niu(方小牛),DAI Mei-Zhen(戴美珍),LI XiaoHong(李晓红),et al.Chemical Research and Application(化学研究与应用),2009,21(5):680-684
[11]LIU Sheng-Li(刘胜利),CHEN Yong(陈勇),DAI Jing-Fang(戴静芳),et al.Chinese Journal of Synthetic Chemistry(合成化学),2004,12:219-221
[12]Chandrasekhar V,Thirumoorthi R,Metre R K,et al.J.Organomet.Chem.,2011,696:600-606
[13]Ruan B,Tian Y,Zhou H,et al.Inorg.Chim.Acta,2011,365:302-308
[14]Xiao X,Du D,Tian M,et al.J.Organomet.Chem.,2012,715:54-63
[15]Yoder C H,Margolis L A,Horne J M.J.Organomet.Chem.,2001,633:33-38
[16]Tang W X,Xiang Y,Tong A J.J.Org.Chem.,2009,74:2163-2166