CN113354645A - 吴茱萸碱的制备及在防治农业害虫方面的应用 - Google Patents
吴茱萸碱的制备及在防治农业害虫方面的应用 Download PDFInfo
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- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
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Abstract
本发明公开的吴茱萸碱是具有式I的化合物。采用在三氟乙酸酐、三乙烯二胺、N,N‑二甲基乙酰胺和原甲酸三乙酯存在下,色胺和N‑甲基靛红酸酐反应制备吴茱萸碱。本发明的吴茱萸碱对东方粘虫,小菜蛾,棉铃虫,玉米螟,草地贪夜蛾等具有一定的杀虫活性,其可以与现有的杀虫剂交替使用,是一种具有广阔应用前景的杀虫剂。
Description
技术领域
本发明属于农用杀虫剂技术领域,涉及含N杂原子的生物碱类化合物的杀虫剂,具体的说是吴茱萸碱的制备及在防治农业害虫方面的应用。
背景技术
植物源杀虫剂指以植物产生的具有杀虫活性的次生代谢产物,如生物碱、黄酮类、萜类、精油类、光活化毒素类等开发的农药制剂。植物源杀虫剂和与传统化学合成杀虫剂相比具有突出优点:(1)来源丰富,可以直接从天然产物中开发得到某些商品化杀虫剂;(2)有良好的环境相容性,在环境中能自然迅速降解,对环境污染小,符合人类与环境和谐发展的要求;(3)具有靶标专一性,对人畜等非靶标生物比较安全,有利于保持生态平衡;(4)作用方式多种多样,避免了纯化学的杀虫方式,使害虫不易产生抗药性,保证了杀虫效果;(5)某些植物源杀虫剂对作物还具有营养作用,可提高农产品的营养价值。基于以上优势,植物源杀虫剂越来越受到人们的关注和研究,现已成为生态型杀虫剂研制的热点。
吴茱萸(Evodia rutaecarpa(Juss.)Benth.)是一种芸香科(Rutaceae)植物,主要产于中国长江以南的较为温暖地区。吴茱萸是一种古老的传统中药植物,具有散寒止痛,降逆止呕,助阳止泻等功效。近年来,国内外研究发现吴茱萸含有多种化学活性成分,主要包括生物碱、挥发油、苦味素等,具有抗肿瘤、抗病毒、抗菌等活性,受到人们广泛的关注和研究。但是,关于吴茱萸的研究主要集中在医用研究上,而在防治农业病虫害方面的研究较少。《中国土农药志》中早期记载:将吴茱萸叶子捣碎后,加水形成液体,喷洒于作物上,不仅可以防治蚜虫、螟虫和棉蚜虫,而且可以有效的防治蛆与孑孓。研究发现吴茱萸中分离得到的吴茱萸碱、吴茱萸次碱、吴茱萸酰胺、吴茱萸醇和柠檬苦素对白纹伊蚊幼虫和南方根结线虫均具有杀虫活性,其中吴茱萸碱和吴茱萸次碱的杀虫活性较为突出,对白纹伊蚊幼虫半数致死浓度LC50值分别为12.51mg/L和17.02mg/L。基于此,本发明报道了吴茱萸碱的制备方法,及其在防治农业害虫方面的应用。
发明内容
本发明的目的在于提供吴茱萸碱的制备方法和防治农业害虫方面的应用。该类化合物具有高效的杀菌活性,可应用于对各种作物上菌害的防治。
本发明提供的吴茱萸碱具有如式I所示的结构式:
本发明采取如下合成线路制备吴茱萸碱:
将式II色胺和式III N-甲基靛红酸酐加入到含有三氟乙酸酐的原甲酸三乙酯和N,N-二甲基乙酰胺溶液中,然后加入三乙烯二胺,加热到100℃,维持5小时。反应完成后,向反应溶液加入饱和食盐水,用乙酸乙酯萃取,收集有机层,浓缩,重结晶得到吴茱萸碱。
本发明的式I化合物吴茱萸碱对东方粘虫,小菜蛾,棉铃虫,玉米螟,草地贪夜蛾等农业害虫具有一定的杀虫活性。
本发明还包括以式I化合物吴茱萸碱为活性成分与农业上可接受的助剂组成农药组合物用于对农业害虫防治的用途。
与现有技术相比,本发明合成了绿色生态型植物源杀虫剂吴茱萸碱,其可以与现有的杀虫剂交替使用,避免或延缓抗性产生,制备条件常规、后续处理简便,易于实现工业化,是一种具有广阔应用前景的杀虫剂。
具体实施方式
下面将结合本发明实施例,对本发明实施例中的技术方案进行清楚、完整地描述,其目的是能更好地理解本发明的内容乃体现本发明的实质性特点。这里也特别指出实施例中所涉及的具体实验方法和设备如无特殊说明,均为常规方法或按照制造厂商说明书建议的条件实施,所涉及的试剂无特殊说明均为市售。
制备式I化合物吴茱萸碱
室温将式II色胺(10mmol)和式III N-甲基靛红酸酐(10mmol)加入到含有三氟乙酸酐(10mmol)的原甲酸三乙酯(7mL)和N,N-二甲基乙酰胺(3mL)溶液中,然后加入三乙烯二胺(15mmol),将反应加热到100℃,维持5小时。反应完成后,向反应溶液加入饱和食盐水(80mL),用乙酸乙酯(50mL)萃取三次,收集有机层,浓缩,重结晶得到白色固体,即为吴茱萸碱,产量2.5g,产率83%。
本发明合成的吴茱萸碱杀虫活性测试。
测试靶标:东方粘虫、小菜蛾、棉铃虫、玉米螟草地贪夜蛾。
测试方法:
测试靶标:东方粘虫(Mythimna separata Walker)。测试方法:浸叶法。用玉米叶浸渍于丙酮配制的药液中,待药液干后接入3龄幼虫,主要为胃毒、触杀作用,同时观察幼虫取食现象。以含有1mL试验溶剂的水溶液为空白对照。处理后72h检查幼虫存活状态,以毛刷轻触幼虫体表,无反应判定为死亡,记录死亡数、存活数,计算死亡率及校正死亡率。
测试靶标:小菜蛾(Plutella Xylostella)。测试方法:浸叶法,置于配制好的所需浓度100ml烧杯中。将处理放入标准处理室内,以含有1mL试验溶剂的水溶液为空白对照。处理后72h检查幼虫存活状态,以毛刷轻触幼虫体表,无反应判定为死亡,记录死亡数、存活数,计算死亡率及校正死亡率。
测试靶标:棉铃虫(Helicoverpa armigera)。测试方法:浸叶法。用玉米叶浸渍于丙酮配制的药液中,待药液干后接入3龄幼虫,主要为胃毒、触杀作用,同时观察幼虫取食现象。以含有1mL试验溶剂的水溶液为空白对照。处理后72h检查幼虫存活状态,以毛刷轻触幼虫体表,无反应判定为死亡,记录死亡数、存活数,计算死亡率及校正死亡率。
测试靶标:玉米螟(Ostrinia nubilalis Hubner)。测试方法:浸叶法。用玉米叶浸渍于丙酮配制的药液中,待药液干后接入3龄幼虫,主要为胃毒、触杀作用,同时观察幼虫取食现象。以含有1mL试验溶剂的水溶液为空白对照。处理后72h检查幼虫存活状态,以毛刷轻触幼虫体表,无反应判定为死亡,记录死亡数、存活数,计算死亡率及校正死亡率。
测试靶标:草地贪夜蛾(Spodoptera frugiperda)。测试方法:浸叶法。将大喇叭口期幼嫩玉米叶片剪为5cm叶段,浸渍药液10s,自然晾干后置于玻璃培养皿(直径75mm)中。选取发育整齐的2龄幼虫饥饿处理4h后接入处理后的叶片。以含有1mL试验溶剂的水溶液为空白对照。处理后72h检查幼虫存活状态,以毛刷轻触幼虫体表,无反应判定为死亡,记录死亡数、存活数,计算死亡率及校正死亡率。
表1吴茱萸碱的杀虫活性(%)
注:同一浓度下杀虫活性强弱*****:>90%;****:>70%;***:>50%;**:>30%;*:>10%
由表1可以看出,植物源杀虫活性物质吴茱萸碱对鳞翅目害虫东方粘虫、小菜蛾、棉铃虫、玉米螟和草地贪夜蛾均具有一定的杀虫活性,尤其对棉铃虫杀虫活性最为突出,因此吴茱萸碱可以作为潜在绿色生态杀虫剂作进一步研究。
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CN113788856A (zh) * | 2021-10-20 | 2021-12-14 | 青岛农业大学 | 一组肟酯硫代磷酰胺化合物及其制备方法和应用 |
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CN117941700A (zh) * | 2024-03-26 | 2024-04-30 | 西南林业大学 | 一种防治三七黑斑病的植物源杀菌剂 |
CN117941700B (zh) * | 2024-03-26 | 2024-06-04 | 西南林业大学 | 一种防治三七黑斑病的植物源杀菌剂 |
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