3（2H）-哒嗪酮衍生物的设计、合成与生物活性研究
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摘要
随着人们环境保护意识的日渐加强和传统杀虫剂显示出的弊端，昆虫生长调节剂(insect growth regulators，简称IGRs)以其独特的作用机制，良好的防治效果，对人类、天敌及环境安全而备受瞩目，被誉为“理想的环境安全化合物”、“21世纪的农药”和“特异性昆虫调控剂”，在害虫综合防治中发挥着越来越重要的作用。
本论文在总结前人研究含哒嗪酮环类似物的基础上，采用活性亚结构连接法，将拟除虫菊酸部分以及新烟碱类杀虫剂的活性基团与哒嗪酮相连接，设计出两类具有全新骨架的化合物(见下图Ⅰ和Ⅱ)，并以二氯代丁烯醛酸为起始原料经5～6步反应共合成出19个化合物，所有化合物均通过~1HNMR、IR和元素分析确证，并对它们的光谱性质也进行了分析。本论文还通过反应温度、溶剂和其他反应试剂对制备重要中间体5-(2-溴乙氧基)-2-叔丁基-4-氯-3(2H)-哒嗪酮和5-(2-羟基乙氧基)-2-叔丁基-4-氯-3(2H)-哒嗪酮的影响进行了研究，确定了优化的实验方案。本论文还探讨了不同杂环与5-取代哒嗪酮反应的活性。
其中，R为Cl、Br、CF_3，R~1为t-C_4H_9，PhCH_2，PhCOCH_2，Y为S、NCN、NNO_2，X为S、NH、NCH_3、NC_2H_5，Z为O，n为0或1。
初步生测试验结果表明，部分目标化合物在500mg／L浓度下对家蝇(Musea domestica Linnaeus)、赤拟谷盗(Tribolium castaneum Herbst)、棉铃虫(Helicoverpa armigera Hubner)和东亚飞蝗(Locusta migratoria manilensis Linne)的幼虫有一定的杀虫活性，其中化合物Y3-1、Y3-3、Y3-12、Y3-14、Y3-15对家蝇2龄幼虫的生长有明显抑制，具有典型的昆虫生长调节剂的活性，其死亡率分别为65.0％、70.0％、77.5％、62.5％、62.5％(对照药剂米螨的死亡率为72.5％)。Ⅱ系列部分化合物对3龄蝗蝻有较好的生物活性和抑制蝗蝻蜕皮的作用，如目标化合物Y3-4、Y3-6、Y3-8、Y3-9在120小时对蝗蝻的死亡率(生长抑制率)分别为75.0％(90.0％)、75.0％(95.0％)、75.0％(80.0％)、75.0％(95.0％)，对照药剂卡死克的120小时的蝗蝻死亡率(生长抑制率)为85.0％(90.0％)。
Along with human paying more attention to environments protection and showing the disadvantage of the traditional insecticides, Insect growth regulators (IGRs) with high potency, good selectivity and pleasant safety to environment and non-target organism, are regarded as 'the perfect compounds friendly to environment', 'the ideal pesticides in 21st century' and 'novel insect regulators'. Because of playing an important role of IGRs in Integrated Pest Management system, it becomes necessary to develop new IGRs to meet the needs of controlling pests in sustainable agriculture.
In this thesis, two types of 3(2H)-pyridazinone derivates were designed by the method of linking active sub-structures of chrysanthemate ester or novel nicotinic heterocycle groups with 3(2H)-pyridazinone. Nineteen new compounds were synthesized in 5-6 steps with the starting material of 2,3-Dichloro-4-oxo-but-2-enoic acid. Their synthetic methods were mainly studied in this paper. Their structures were confirmed by 'H-NMR, IR and elemental analysis, and their spectra were also analysized. The synthesis methods of two pyridazinone intermediates [5-(2-Bromo-ethoxy)-2-tert-butyl-4-chloro-2H-pyridazin-3-one and 5-(2-hydroxy-ethoxy)-2-tert-Butyl-4-chloro-2H-pyridazin-3-one] were disscussed. The reaction activity of different heterocycles and 5-(2-bromo-ethoxy)-4-chloro -2H-pyridazin-3-one were also studied.
In the preliminary bioassay test, most compounds have been showed growth inhibition against houseflies (Musea domestica Linnaeus), cotton boll worm(Helicoverpa armigera Hubner), red flour beetles (Tribolium castaneum Herbst) and asiatic locust(Locusta migratoria manilensis Linne)in the concentration of 500mg/L. The compounds of Y3-1, Y3-3, Y3-12, Y3-14 and Y3-15 inhibited the growth of housefly second larval, the mortality rates were 65.0%, 70.0%, 77.5%, 62.5% and 62.5%, respectively. The mortality of tebufenozide was 72.5%. Some compounds of type II showed good biological activity, inhibited growth of locust third larval. The mortality rates (growth inhibition rates) of Y3-4, Y3-6, Y3-8, Y3-9 and flufenoxuron were 75.0%(90.0%), 75.0%(95.0%), 75.0%(80.0%), 75.0%(95.0%), 85.0%(90.0%) after 120 hour.
本论文在总结前人研究含哒嗪酮环类似物的基础上，采用活性亚结构连接法，将拟除虫菊酸部分以及新烟碱类杀虫剂的活性基团与哒嗪酮相连接，设计出两类具有全新骨架的化合物(见下图Ⅰ和Ⅱ)，并以二氯代丁烯醛酸为起始原料经5～6步反应共合成出19个化合物，所有化合物均通过~1HNMR、IR和元素分析确证，并对它们的光谱性质也进行了分析。本论文还通过反应温度、溶剂和其他反应试剂对制备重要中间体5-(2-溴乙氧基)-2-叔丁基-4-氯-3(2H)-哒嗪酮和5-(2-羟基乙氧基)-2-叔丁基-4-氯-3(2H)-哒嗪酮的影响进行了研究，确定了优化的实验方案。本论文还探讨了不同杂环与5-取代哒嗪酮反应的活性。
其中，R为Cl、Br、CF_3，R~1为t-C_4H_9，PhCH_2，PhCOCH_2，Y为S、NCN、NNO_2，X为S、NH、NCH_3、NC_2H_5，Z为O，n为0或1。
初步生测试验结果表明，部分目标化合物在500mg／L浓度下对家蝇(Musea domestica Linnaeus)、赤拟谷盗(Tribolium castaneum Herbst)、棉铃虫(Helicoverpa armigera Hubner)和东亚飞蝗(Locusta migratoria manilensis Linne)的幼虫有一定的杀虫活性，其中化合物Y3-1、Y3-3、Y3-12、Y3-14、Y3-15对家蝇2龄幼虫的生长有明显抑制，具有典型的昆虫生长调节剂的活性，其死亡率分别为65.0％、70.0％、77.5％、62.5％、62.5％(对照药剂米螨的死亡率为72.5％)。Ⅱ系列部分化合物对3龄蝗蝻有较好的生物活性和抑制蝗蝻蜕皮的作用，如目标化合物Y3-4、Y3-6、Y3-8、Y3-9在120小时对蝗蝻的死亡率(生长抑制率)分别为75.0％(90.0％)、75.0％(95.0％)、75.0％(80.0％)、75.0％(95.0％)，对照药剂卡死克的120小时的蝗蝻死亡率(生长抑制率)为85.0％(90.0％)。
Along with human paying more attention to environments protection and showing the disadvantage of the traditional insecticides, Insect growth regulators (IGRs) with high potency, good selectivity and pleasant safety to environment and non-target organism, are regarded as 'the perfect compounds friendly to environment', 'the ideal pesticides in 21st century' and 'novel insect regulators'. Because of playing an important role of IGRs in Integrated Pest Management system, it becomes necessary to develop new IGRs to meet the needs of controlling pests in sustainable agriculture.
In this thesis, two types of 3(2H)-pyridazinone derivates were designed by the method of linking active sub-structures of chrysanthemate ester or novel nicotinic heterocycle groups with 3(2H)-pyridazinone. Nineteen new compounds were synthesized in 5-6 steps with the starting material of 2,3-Dichloro-4-oxo-but-2-enoic acid. Their synthetic methods were mainly studied in this paper. Their structures were confirmed by 'H-NMR, IR and elemental analysis, and their spectra were also analysized. The synthesis methods of two pyridazinone intermediates [5-(2-Bromo-ethoxy)-2-tert-butyl-4-chloro-2H-pyridazin-3-one and 5-(2-hydroxy-ethoxy)-2-tert-Butyl-4-chloro-2H-pyridazin-3-one] were disscussed. The reaction activity of different heterocycles and 5-(2-bromo-ethoxy)-4-chloro -2H-pyridazin-3-one were also studied.
In the preliminary bioassay test, most compounds have been showed growth inhibition against houseflies (Musea domestica Linnaeus), cotton boll worm(Helicoverpa armigera Hubner), red flour beetles (Tribolium castaneum Herbst) and asiatic locust(Locusta migratoria manilensis Linne)in the concentration of 500mg/L. The compounds of Y3-1, Y3-3, Y3-12, Y3-14 and Y3-15 inhibited the growth of housefly second larval, the mortality rates were 65.0%, 70.0%, 77.5%, 62.5% and 62.5%, respectively. The mortality of tebufenozide was 72.5%. Some compounds of type II showed good biological activity, inhibited growth of locust third larval. The mortality rates (growth inhibition rates) of Y3-4, Y3-6, Y3-8, Y3-9 and flufenoxuron were 75.0%(90.0%), 75.0%(95.0%), 75.0%(80.0%), 75.0%(95.0%), 85.0%(90.0%) after 120 hour.
引文
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