【作者】 占升卫；

【导师】 马敬中；

【作者基本信息】 华中农业大学 ， 农药学， 2007， 硕士

【摘要】 化学除草剂是农业生产的重要保障。现有商品除草剂在除草效果与环境保护方面仍不能满足社会发展的需要。故研制高效安全的新除草剂成了农药研究领域最热门的课题。本课题组在近几年研究中发现二氮氧化喹喔啉甲醛衍生物具有明显的除草活性。本课题将具有生物活性的取代环戊酮与二氮氧化喹喔啉甲醛拼接，探求新化合物的除草活性。本论文在前期研究的基础上完成了如下工作：1．以邻硝基苯胺为原料，合成了苯并呋咱-N-氧化物；用苯并呋咱-N-氧化物与丙酮经Beirut反应合成了2-甲基二氮氧化喹喔啉；2-甲基二氮氧化喹喔啉用二氧化硒氧化生成二氮氧化喹喔啉-2-甲醛中间体。反应方程式如下：2．合成以下两种不同类型的取代环戊酮中间体10种。反应方程式如下：3．尝试合成以下两种取代环戊酮：反应式如下：4．取代环戊酮与肼反应生成单腙中间体10种。反应式如下：5．取代环戊酮单腙与二氮氧化喹喔啉甲醛反应，合成了10种二氮氧化喹喔啉甲醛双腙。反应式如下：6．对涉及上述相关化学反应的反应条件进行了探讨，优化了反应条件。对合成的10种二氮氧化喹喔啉甲醛双腙的结构进行了表征。7．用10种合成的新化合物对单子叶植物水稻、稗草和双子叶植物油菜、野苋菜进行了除草活性方面的实验，测定了新化合物在不同质量浓度下对水稻、稗草和油菜、野苋菜的除草活性。实验结果表明，除草活性随新化合物的品种、浓度和植物品种不同而异。1，4-二氮氧化喹喔啉-2-甲醛-2′-(二甲氨基甲基)环戊酮双腙、1，4-二氮氧化喹喔啉-2-甲醛-2′-二甲基亚甲基环戊酮双腙在400mg／L对稗草具有致死作用，浓度越高，效果越明显。1，4-二氮氧化喹喔啉-2-甲醛-2′-正丙基亚甲基环戊酮双腙在高浓度800mg／下可以杀死稗草和野苋菜。1，4-二氮氧化喹喔啉-2-甲醛-2′-乙基亚甲基环戊酮双腙在各种浓度下可以杀死稗草、油菜和野苋菜，在浓度高于400mg／L时还可以杀死水稻。总体来说，新化合物对单子叶植物的抑制活性高于对双子叶植物。本论文为一类新型除草活性化合物二氮氧化喹喔啉甲醛衍生物的合成与除草活性研究积累了科研数据。更多还原

【Abstract】 Chemical herbicides have extensive application in agriculture. But, the herbicides can not meet the need of the human beings in the field of herbicidal activity and environment protection. The development of novel herbicides has become the most hot subject in pesticide field.Recently, we find derivatives of di-N-oxide quinoxaline formaldehyde have obvious herbicidal activity. They can be potential and novel herbicides. Substituted cyclopentanones have biological activity, and new derivatives of di-N-oxide quinoxaline formaldehyde which have the structure of them are synthesized and screened for herbicidal activity.Base on our early research, this paper accomplished the works as follows:1.Benzofurazane was synthesized using o-nitroaniline, followed by reacting with acetone to produce the methyl di-N-oxide quinoxaline through Beirut reaction. The product was oxidized by selenium dioxide to form the di-N-oxide quinoxaline formaldehyde.The chemical equation as follows:2.Ten kinds of substituted cyclopentanones which belong to two different types had been synthesized.The chemical equation as follows: 3.Attempted to synthesize two kinds of substituted cyclopentanones below.4. Ten kinds of single hydrazone were obtained by reaction of substituted cyclopentanones with hydrazine hydrate respectively.The chemical equation as follows:5. Ten kinds of 1, 4-dioxoquinoxaline formaldehyde dihydrazones were obtained by reaction of single hydrazone with 1, 4-dioxoquinoxaline formaldehyde.The chemical equation as follows:6 The investigation of correlative reaction conditions was carried out in order to improve the rate of production. And the structures of some final products were characterized. 7. Monocotyledon Oryza sativa、Echinochloa Beauvois and dicotyledon Amaranthus ascendens Loisel、Canola were selected as biomarker to testify the herbicidal activity of final products by measuring the herbicidal activity on different mass concentration of final products.The result shows that, the herbicidal activity varies from different species and concentration of novel compounds. 1, 4-dioxoquinoxaline formaldehyde -2’-(methyl amino methyl) cyclopentanone dihydrazones and 1, 4-dioxoquinoxaline formaldehyde -2’-dimethylidene cyclopentanone dihydrazones can kill Echinochloa Beauvois When the mass concentration of the two compounds is 400mg/L, and the thicker mass concentration, the better herbicidal activity. 1, 4-dioxoquinoxaline formaldehyde -2’-n-propanalidene cyclopentanone dihydrazones can kill Echinochloa Beauvois and Amaranthus ascendens Loisel When the mass concentration of the compound is 800mg/L. 1, 4-dioxoquinoxaline formaldehyde-2’-ethylidene cyclopentanone dihydrazones can kill Echinochloa Beauvois and Canola and Amaranthus ascendens Loisel on different mass concentrations. It also can kill Oryza sativa when the mass concentration is above 400 mg/L.That all, the herbicidal activity of novel compounds to monocotyledon is better than to dicotyledon.This paper accumulated the scientific research data for synthesis and herbicidal activity of a late-model kind of derivatives of quinoxaline di-N-oxide formaldehyde.更多还原