含异噁唑环的2，5-二取代-1，3，4-噁二唑化合物的合成及杀菌活性
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摘要
杂环化合物的合成和生物活性的研究一直是有机化学、农药化学及药物化学最具有生命力的研究领域一,大量文献报道了杂环化合物具有良好的杀菌活性,近年来该类化合物在农药和医药领域的应用也越来越广泛。在已开发的众多的杂环化合物中,1,3,4-噁二唑类化合物因为具有广谱生物活性诸如杀虫、抗菌、抗癌和抗炎,尤其是温和的杀菌和抗菌活性而受到众多科研工作者的关注。
本文对1,3,4-噁二唑类化合物的生物活性、作用机制与合成方法以及异噁唑类化合物的生物活性和合成方法做了比较全面的综述。为了寻找高活性的农药品种,利用生物等排原理和亚结构连接法,对1,3,4-噁二唑类化合物的母体进行了修饰,将具有较好生物活性的取代异噁唑类化合物引入到1,3,4-噁二唑类化合物的分子中,以对氯苯甲醛、对三氟甲基苯甲醛、盐酸羟胺、N-氯代丁二酰亚胺、乙酰乙酸乙酯、水合肼、取代苯胺和醋酸汞为原料合成了两个系列的10种2-取代苯胺基-5-(取代异噁唑-4-基)-1,3,4-噁二唑新化合物(I、II)。
I. 2-取代苯胺基-5-[5-甲基-3-(4-氯苯基)-4-异噁唑-4-基]-1,3,4-噁二唑
II. 2-取代苯胺基-5-[5-甲基-3-(4-三氟甲基苯基)-4-异噁唑-4-基]-1,3,4-噁二唑所合成的10种新化合物的结构经1HNMR、IR和元素分析确证。本文对实验方法进行详细的讨论并对部分实验过程作了改进,提高目标化合物的产率。对目标化合物的光谱性质进行系统的分析与讨论,确定核磁共振氢谱及红外光谱吸收峰的归属。
用国家“八五”新农药创制的生物测定标准方法(生长速率法)对所合成的I、II两个系列化合物进行了初步的生物活性测试,分别测定其对番茄灰霉病菌和小麦纹枯病菌的室内抑制活性,结果表明部分化合物对番茄灰霉病菌表现出较好的抑制活性,化合物I_c、I_d、II_b、II_d、II_e的EC_(50)分别为24.88、18.15、16.89、14.03和19.83μg/mL,均低于对照药剂多菌灵(48.68μg/mL)。说明把取代异噁唑环和取代苯环按活性基团拼接原理引入到1,3,4-噁二唑类化合物结构中,其生物活性得到了加强。
The study of the synthetical methods and the biological activity of heterocyclic compounds has always been the search realm with vitality in the organic chemistry, pesticide chemistry and medical chemistry, a great deal of literature reported that heterocyclic compounds had antifungal bioactivities, in recent years heterocyclic compounds have also attracted considerable attention in pesticide and medicinal formulation. In numerous developed miscellaneous in heterocyclic compounds, 1,3,4-oxadiazole derivatives have received increasing interests in diverse potential biological properties such as inseticidal, anticancer and anti-inflammatory activities, especially their unique antifungal.
By consulting concerned literatures, we reviewed more comprehensively the biological activities, effective mechanism and synthetical methods of 1,3,4-oxadiazole derivatives and bioactivity, synthetical methods of of isoxazolyl compounds. In order to seek insecticides with good biological activities, we have modified the main structure of acylureas by Bioisosterism Principles and Structure Link Wory, introduce isoxazolyl compounds into 1,3,4-oxadiazole. Ten novel compounds of 2-substituted phenylamino-5-(substituted isoxazol-4-yl)-1,3,4-oxadiazoles (I, II) were synthesized with 4-chlorobenzaldehyde, 4-(trifluoromethyl) benzaldehyde, Hydroxylamine hydrochloride, N-Chloro Succinimide, ethylacetoacetate, Hydrazine, substituted aniline and mercuric acetate as materials.
The title compounds are listed as follows:
I 2-substituted phenylamino-5- [5-methyl-3-(4-chlorphenyl)-4-substituted isoxazol-4-yl]-1,3,4-oxadiazoles.
II 2-substituted phenylamino-5- [5-methyl-3-(4-trifluoromethylphenyl)-4-substituted isoxazol-4-yl)-1,3,4-oxadiazoles. Structures of teen novel compounds were characterized by IR, 1H NMR spectra and elemental analysis. Based on the idiographic structure, we discuss synthes is condition, spectrum properties and physic-chemical constant of the target compounds at last.
In the article, the biological activities of the target compounds were determined by bioassay standard method (the mycelium growth rate method) created by national“85”novel pesticide. The antifungal activities of two series compounds (I, II)against Botrytis cinereapers and Rhizoctonia cereailes were respectively tested by, and the results indicated that they had good antifungal activity against Botrytis cinerea pers, the numerical EC50 of Ic, Id, IIb, IId, IIe is 24.88, 18.15, 16.89, 14.03 and 19.83μg/mL, which is less than carbendazim’s numerical (48.68μg/mL). The results indicate that the activies are increased when we modify the main structure of 1,3,4-oxadiazole derivatives by Bioisosterism Principles, and connected substituted isoxazoly and substituted aniline with the main structure.
本文对1,3,4-噁二唑类化合物的生物活性、作用机制与合成方法以及异噁唑类化合物的生物活性和合成方法做了比较全面的综述。为了寻找高活性的农药品种,利用生物等排原理和亚结构连接法,对1,3,4-噁二唑类化合物的母体进行了修饰,将具有较好生物活性的取代异噁唑类化合物引入到1,3,4-噁二唑类化合物的分子中,以对氯苯甲醛、对三氟甲基苯甲醛、盐酸羟胺、N-氯代丁二酰亚胺、乙酰乙酸乙酯、水合肼、取代苯胺和醋酸汞为原料合成了两个系列的10种2-取代苯胺基-5-(取代异噁唑-4-基)-1,3,4-噁二唑新化合物(I、II)。
I. 2-取代苯胺基-5-[5-甲基-3-(4-氯苯基)-4-异噁唑-4-基]-1,3,4-噁二唑
II. 2-取代苯胺基-5-[5-甲基-3-(4-三氟甲基苯基)-4-异噁唑-4-基]-1,3,4-噁二唑所合成的10种新化合物的结构经1HNMR、IR和元素分析确证。本文对实验方法进行详细的讨论并对部分实验过程作了改进,提高目标化合物的产率。对目标化合物的光谱性质进行系统的分析与讨论,确定核磁共振氢谱及红外光谱吸收峰的归属。
用国家“八五”新农药创制的生物测定标准方法(生长速率法)对所合成的I、II两个系列化合物进行了初步的生物活性测试,分别测定其对番茄灰霉病菌和小麦纹枯病菌的室内抑制活性,结果表明部分化合物对番茄灰霉病菌表现出较好的抑制活性,化合物I_c、I_d、II_b、II_d、II_e的EC_(50)分别为24.88、18.15、16.89、14.03和19.83μg/mL,均低于对照药剂多菌灵(48.68μg/mL)。说明把取代异噁唑环和取代苯环按活性基团拼接原理引入到1,3,4-噁二唑类化合物结构中,其生物活性得到了加强。
The study of the synthetical methods and the biological activity of heterocyclic compounds has always been the search realm with vitality in the organic chemistry, pesticide chemistry and medical chemistry, a great deal of literature reported that heterocyclic compounds had antifungal bioactivities, in recent years heterocyclic compounds have also attracted considerable attention in pesticide and medicinal formulation. In numerous developed miscellaneous in heterocyclic compounds, 1,3,4-oxadiazole derivatives have received increasing interests in diverse potential biological properties such as inseticidal, anticancer and anti-inflammatory activities, especially their unique antifungal.
By consulting concerned literatures, we reviewed more comprehensively the biological activities, effective mechanism and synthetical methods of 1,3,4-oxadiazole derivatives and bioactivity, synthetical methods of of isoxazolyl compounds. In order to seek insecticides with good biological activities, we have modified the main structure of acylureas by Bioisosterism Principles and Structure Link Wory, introduce isoxazolyl compounds into 1,3,4-oxadiazole. Ten novel compounds of 2-substituted phenylamino-5-(substituted isoxazol-4-yl)-1,3,4-oxadiazoles (I, II) were synthesized with 4-chlorobenzaldehyde, 4-(trifluoromethyl) benzaldehyde, Hydroxylamine hydrochloride, N-Chloro Succinimide, ethylacetoacetate, Hydrazine, substituted aniline and mercuric acetate as materials.
The title compounds are listed as follows:
I 2-substituted phenylamino-5- [5-methyl-3-(4-chlorphenyl)-4-substituted isoxazol-4-yl]-1,3,4-oxadiazoles.
II 2-substituted phenylamino-5- [5-methyl-3-(4-trifluoromethylphenyl)-4-substituted isoxazol-4-yl)-1,3,4-oxadiazoles. Structures of teen novel compounds were characterized by IR, 1H NMR spectra and elemental analysis. Based on the idiographic structure, we discuss synthes is condition, spectrum properties and physic-chemical constant of the target compounds at last.
In the article, the biological activities of the target compounds were determined by bioassay standard method (the mycelium growth rate method) created by national“85”novel pesticide. The antifungal activities of two series compounds (I, II)against Botrytis cinereapers and Rhizoctonia cereailes were respectively tested by, and the results indicated that they had good antifungal activity against Botrytis cinerea pers, the numerical EC50 of Ic, Id, IIb, IId, IIe is 24.88, 18.15, 16.89, 14.03 and 19.83μg/mL, which is less than carbendazim’s numerical (48.68μg/mL). The results indicate that the activies are increased when we modify the main structure of 1,3,4-oxadiazole derivatives by Bioisosterism Principles, and connected substituted isoxazoly and substituted aniline with the main structure.
引文
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