嘧霉胺氯乙酸盐的晶体结构及杀菌活性

Crystal Structure and Fungicidal Activity of N-(4,6-Dimethylpyrimidin-2-yl) Aniline Chloroacetate

为寻找高活性的嘧啶类杀菌剂,由N-(4,6-二甲基嘧啶-2-基)苯胺(嘧霉胺)和氯乙酸在无水乙醇介质中反应合成了新化合物嘧霉胺氯乙酸盐,通过元素分析、红外分析、核磁共振氢谱分析对其结构进行了确证,用X射线单晶衍射测定了晶体结构,并对其杀菌活性进行了测试.结果表明:嘧霉胺氯乙酸盐晶体属于单斜晶系,空间群P4(2)/n,晶胞参数为:a=(1.9604±0.0004)nm,b=(1.9604±0.0004)nm,c=(0.7542±0.0003)nm,β=90°,V=(2.8986±0.001 3)nm^3,D_c=11 324g·cm^3,Z=8,F(000)=1232,μ=0.27mm^(-1);嘧霉胺氯乙酸盐晶体结构中,氯乙酸根阴离子和N-(4,6-二甲基嘧啶-2-基)苯胺基阳离子之间通过N—H和O形成的氢键连接在一起;在阳离子中,嘧啶环和苯环形成的二面角是(7.59±0.04)°;该化合物具有优异的杀菌活性。

In order to obtain a high-activity pyrimidine fungicide, a new compound N-（4,6-dimethylpyrimidin-2- yl） aniline chloroacetate was synthesized via the reaction of pyrimethanil and ehloroaeetic acid in anhydrous ethanol and was then identified by means of elemental analysis, IR and 1H NMR. Moreover, the crystal structure of the compound was determined via single-crystal XRD, and the fungicidal activity was finally measured. The results indicate that （ 1 ） the crystal is monoclinic in a space group of P4 （2）/n, with the crystal parameters being as follows ： a = （1. 9604 ±0.0004） nm, 6 = （1. 9604 ±0. 0004） nm, c = （0.7542±0. 0003） nm, β =90°, V= （2. 8986 ± 0. 0013） nm3 ,De = 11324g· cm3, Z =8, F（000） = 1232,μ =0.27mm-1 ; （2） in the compound crystal, ehloroacetate anions are linked to N-（4,6-dimethylpyrimidin-2-yl）-aniline cations via N-H…O hydrogen bonding; （3） within the cations, the pyrimidine ring is twisted with respect to the phenyl ring in a dihedral angle of （7.59 - 0.04） °; and （4） the synthesized compound is of high fungicidal activity.