【作者】 王蓓；

【导师】 张千峰；

【作者基本信息】 安徽工业大学 ， 分析化学， 2019， 硕士

【摘要】 异噻菌胺（3,4-二氯-N-（2-氰基苯基）-5-异噻唑甲酰胺）是第一个使用量低、对环境友好且有诱导抗性的杀菌剂,主要用于水稻稻瘟病的防治。然而,异噻菌胺的生产工艺存在低收率和纯度不高等方面的问题,为此,本论文系统总结了异噻唑类化合物的合成路径,并对异噻菌胺产品及其中间体衍生物的合成工艺进行系统地总结探讨改进,并就异噻唑类及其中间体衍生物的合成优化与结构分析进行首次报道。本论文通过研究原料的纯化、原料配比、温度、时间及重结晶的溶剂等因素对异噻菌胺合成收率的影响,优选用水重结晶的3,4-二氯异噻唑-5-甲腈为反应原料,经过水解、酰氯化、傅克酰基化、消去反应及结晶等实验步骤,可重复性地合成出性质稳定、纯度高及产率高的异噻菌胺产品,通过¹H NMR、¹³C NMR、FT-IR及UV-Vis等测试进行分析与表征,并通过单晶X-射线衍射分析测定了异噻菌胺的分子结构,分析惰性药物分子在单胞中的堆积排布状况,产品收率可稳定地达86%,纯度可高达98%。因异噻菌胺结构中的酰胺基是一个药效基团,为此在该基础上,通过对实验条件的探索,合成出系列3,4-二氯异噻唑甲酰胺类化合物和3,5-二氯苯甲酰胺类化合物,通过¹H NMR、FT-IR和UV-Vis等测试进行分析与表征,并通过单晶X-射线衍射分析测定了3,5-二氯-N-（4-氯苯基）苯甲酰胺（B1）和3,5-二氯-N-（2-氯苯基）苯甲酰胺（B3）的分子结构,探讨分子结构氢键的作用力。更多还原

【Abstract】 Isotianil（3,4-dichloro-N-（2-cyanophenyl）-5-isothiazolecarboxamide）is firstlyknown bactericide that is low-used,environmental friendly and inducible,mainly for the prevention and control of the rice blast.However,the production process of isotianil has problems in lower yield along with lower purity.For this reason,syntheses of isothiazoles and the synthetic route of isothiazide-type products and their intermediate derivatives are systemtically summarized and practically reveived in this thesis.And designed syntheses and structural analyses of isothiazoles and their intermediate derivatives are reported for the first time.The effects of reactive factors such as recrystallization of raw materials,the ratio of raw materials,temperature,time and recrystallization solvents on the yield of isotianil have been investigated in the thesis,optimistacally the recrystallized3,4-dichloroisothiazol-5-carbonitrile was directly chosen as a starting materials,and them by using of the hydrolysis reaction,chloride acetylation,Friedel-Crafts reaction,eliminatoin reaction and crystallization,the isothiafen product with stable properties along with high purity and high yield could be repeatedly synthesized.The obtained product was characterized by¹H NMR,¹³C NMR,FT-IR spectroscopies along with the HPLC testing.The molecular structure of isotianil was established by single-crystal X-ray diffraction,and the aggreatration and arrangement of inert drug molecules in the unit cell were analyzed in detail.The final product yield may reach 86%and the purity is as high as 98%.The amide group in the structure of isotianil is a pharmacophore.Based upon the experimental conditions,a series of 3,4-dichloroisothiazole carboxamides derivatives and 3,5-dichlorobenzamide derivatives were synthesized.All of the synthesized compounds were characterized by ¹H NMR,FT-IR and UV-Vis spectroscopic.Molecular structures of 3,5-dichloro-N-（4-chlorophenyl）-5-benzoylamide（B1）and3,5-dichloro-N-（2-chlorophenyl）-5-benzoylamide（B3）were determined by single-crystal X-ray diffraction.Hydrogen-bonding interactions in the molecules were further discussed.更多还原