CN113321655A - 吴茱萸植物源杀虫剂的制备及应用 - Google Patents
吴茱萸植物源杀虫剂的制备及应用 Download PDFInfo
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Abstract
本发明公开了吴茱萸碱衍生物及其制备和应用。本发明化合物具有如I所示的结构式,式中R1和R2具有权利要求1所定义。本发明的通式I化合物对东方粘虫,小菜蛾,棉铃虫,玉米螟,草地贪夜蛾等鳞翅目害虫具有中等到显著的杀虫活性。本发明合成了一类绿色、高效、作用靶标独特的杀虫剂,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。
Description
技术领域
本发明属于农用杀菌剂技术领域,涉及含多个N杂原子的吴茱萸植物源杀虫剂,具体的说是吴茱萸碱衍生物的制备及在防治农业害虫方面的应用。
背景技术
吴茱萸(Evodia rutaecarpa(Juss.)Benth.)是一种芸香科(Rutaceae)药用植物,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。Miyazawa等研究发现吴茱萸果实的甲醇提取液对黑腹果蝇的幼虫和成虫具有毒杀作用,进一步研究证明提取液中的吴茱萸碱对黑腹果蝇幼虫和成虫的半数致死浓度LC50值分别为0.28mg/L和3.58mg/L。中国农科院植保所蒋红云教授课题组研究发现,吴茱萸果实提取物的不同萃取物对3龄甜菜夜蛾具有非选择性拒食活性,其中氯仿萃取物和正丁醇萃取物表现出较高的拒食活性,非选择性拒食中浓度AFC50值分别为1.82mg/L和1.85mg/L。中国农业大学的刘志龙教授课题组早期对40种中草药进行研究发现,吴茱萸果实对谷物储粮害虫赤拟谷盗和玉米象具有杀虫活性,进一步研究发现,吴茱萸果实中的α-水芹烯对赤拟谷盗成虫和幼虫以及玉米象成虫具有很强的熏蒸活性,24小时的半数致死浓度LC50值分别是19.78mg/L,47.96mg/L和15.61mg/L,同时发现β-月桂和β-罗勒烯对上述两种害虫也有熏蒸活性。综上研究表明,吴茱萸是一种具有开发潜力的杀虫植物。
基于吴茱萸的杀虫作用,本课题组也开展了吴茱萸生物碱作为杀虫剂先导化合物潜力的评价。利用现代化学的分离提纯手段,从我国传统中药芸香科植物吴茱萸果实中分离得到了吴茱萸碱、吴茱萸次碱和去氢吴茱萸碱等生物碱单体化合物,采用浸叶法对单体化合物进行了杀虫活性评价,结果发现吴茱萸碱、吴茱萸次碱和去氢吴茱萸碱具有较好的杀虫活性,其中吴茱萸碱的杀虫活性最为突出,可以作为植物源杀虫剂先导化合物做进一步的结构优化,具有潜在的研究和开发价值。基于此,本发明报道了吴茱萸碱衍生物的制备方法及其杀虫活性,这在现有技术中尚未见公开。
发明内容
本发明的目的在于提供吴茱萸碱衍生物及其制备方法和应用。该类化合物具有显著的杀虫活性,可应用于鳞翅目害虫的防治。
本发明提供的吴茱萸碱衍生物具有如通式I所示的结构式:
其中,R1和R2为H、C1-C6烷基、卤代C1-C6烷基、C2-C6烯基、卤代 C2-C6烯基、C2-C6炔基、卤代C2-C6炔基、C3-C6环烷基或卤代C3-C6环烷基;R3为H、C1-C6烷基。
本发明采取如下合成线路制备吴茱萸碱衍生物:
将式II吲哚乙胺经甲酰化和分子内关环得到式III 3,4-二氢-β-咔啉,然后与式IV N-甲基靛红酸酐室温下进行反应,TLC监测反应进程,反应完成后,体系中出现大量固体,过滤洗涤得到式I吴茱萸碱衍生物。反应温度为室温;反应时间通常为8-10小时。
本发明的通式I化合物对东方粘虫,小菜蛾,棉铃虫,玉米螟,草地贪夜蛾等农业鳞翅目害虫具有中等到显著的杀虫活性。
本发明还包括以式I化合物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鳞翅目害虫防治的用途。
与现有技术相比,本发明合成了一类绿色、高效、作用靶标独特的杀虫剂,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,因此所描述的实施例仅仅是本发明一部分实施例,而不是全部的实施例。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。
实施例1
制备1-甲基吴茱萸碱(目标产物I-1)
将10mL二氯甲烷、1mmol N-甲基-8-甲基-靛红酸酐和1mmol 3,4-二氢-β- 咔啉加入25mL双口圆底烧瓶,室温搅拌,体系由浑浊变澄清,10小时后,体系中又重新出现大量固体,减压抽滤,固体用二氯甲烷洗涤,烘干固体得到目标产物1-甲基吴茱萸碱,产量0.27g,产率85%。
实施例2
制备10-甲氧基吴茱萸碱(目标产物1-29)
将10mL二氯甲烷、1mmol N-甲基靛红酸酐和1mmol 6-甲氧基-3,4-二氢-β- 咔啉加入25mL双口圆底烧瓶,室温搅拌,体系由浑浊变澄清,10小时后,体系中又重新出现大量固体,减压抽滤,固体用二氯甲烷洗涤,烘干固体得到目标产物10-甲氧基吴茱萸碱,产量0.25g,产率75%。
采取与实施例1-2相同的制备方法,但采用不同的原料(物质的量同实施例 1-2对应的反应原料相同)制备38种中剩余的36种目标产物,目标产物的物理常数如表1所示、核磁共振氢谱(1H NMR)如表2所示。
表1目标产物(通式I)的物理常数
表2目标产物(通式I)的1H NMR
本发明合成的吴茱萸碱衍生物杀虫活性测试。
测试靶标:东方粘虫(Mythimna separata Walker)、小菜蛾(PlutellaXylostella)、棉铃虫(Helicoverpa armigera)、玉米螟(Ostrinia nubilalis Hubner)、草地贪夜蛾(Spodoptera frugiperda)。
测试方法:
测试靶标:东方粘虫。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。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。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。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。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3目标化合物I的杀虫活性(%)
注:同一浓度下杀虫活性强弱*****:>90%;****:>70%;***:>50%;**:>30%;*:>10%
以上所述仅为本发明的较佳实施例而已,并不用以限制本发明,凡在本发明的精神和原则之内,所作的任何修改、等同替换、改进等,均应包含在本发明的保护范围之内。本发明未具体叙述的部件或连接方式均采用现有技术。本发明所叙述的前侧面、后侧面、左侧面、右侧面均为了方便描述其结构,并不用于限制本发明的保护范围。
Claims (4)
3.权利要求1所述的吴茱萸碱衍生物作用于昆虫鱼尼丁受体,靶标独特,用于制备农用杀虫剂。
4.权利要求1所述的吴茱萸碱衍生物在制备农用杀虫剂中的用途,其特征在于:以式I化合物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东方粘虫,小菜蛾,棉铃虫,玉米螟,草地贪夜蛾等农业鳞翅目害虫防治的用途。
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