类烟碱衍生物的合成及生物活性
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摘要
新烟碱类杀虫剂是以天然烟碱为模型,经结构改进而发现的性能优异的化学杀虫剂,与天然烟碱具有相同的作用方式,即作用于昆虫的烟碱型乙酰胆碱受体(nAChR)。新烟碱类杀虫剂的成功开发是杀虫剂发展史上的一个重大突破,因其杀虫活性高、适当的田间稳定性和持效时间长等优点在虫害防治方面发挥了重要的作用。但是随着新烟碱类杀虫剂使用年限的增加,害虫对其抗药性也日渐增长。因此,开发新型的烟碱类杀虫剂就显得越来越重要。本文以硝基亚甲基(亚胺基)新烟碱类化合物为先导,合成了五类结构新颖的烟碱类化合物,并对其生物活性和构效关系进行了初步的分析。
1.以硝基乙烯基新烟碱类化合物为先导,设计并通过还原的方法合成了20个用传统方法难以合成的不饱和烟碱类醛肟化合物。通过实验分析认为,制备此类醛肟的反应是通过还原硝基的酸式结构进行的,而不是通过通常所认为的硝式结构进行的。单晶分析结果显示,醛肟的羟基处于反式结构。此烟碱类醛肟化合物显示出生物活性的多样性,具有较高的除草活性和中等程度的杀虫活性。化合物Ⅱ-2b(1-(5-氯-2-噻唑甲基)-4,5-二氢咪唑-2-甲醛肟)在100 mg／L的浓度下对马唐和鲤肠地下部分的抑制率达到90%以上；化合物Ⅱ-2g(1-(2-噻吩甲基)-4,5-二氢咪唑-2-甲醛肟)在100 mg/L的浓度下对鲤肠地上／地下部分的抑制率均达到80%以上。化合物Ⅱ-2a(1-(6-氯-3-吡啶甲基)-4,5-二氢咪唑-2-甲醛肟)和Ⅱ-2b在50 mg/L的浓度下对孑孓的杀死率可达100%,在500 mg/L的浓度下对豆蚜的杀死率分别为100%和93%。
2.以不饱和烟碱类醛肟为原料,设计并合成了5个含芳香杂环的反式烟碱类肟醚化合物。并利用该烟碱类醛肟与酰氯反应,通过反应中所产生的酸催化相应的肟酯发生分子内消除-重排反应,设计并合成了12个用传统方法难以合成的烟碱类咪唑醇酯化合物。两类烟碱衍生物显示出生物活性的多样性,具有接近中等程度的杀虫和除草活性。其中化合物Ⅲ-2a(2-氯-苯甲酸-1-(6-氯-3-吡啶甲基)-4,5-二氢咪唑基酯)在100 mg/L的浓度下对马唐地上部分的抑制率为50%,地下部分的抑制率为85%。
3.以硝基乙烯基新烟碱类化合物为原料,设计并合成了37个利用共轭体系和双环结构固定硝基为顺式构型的新烟碱类化合物。所有化合物对孑孓表现出良好的杀灭活性,其中Ⅳ-1f(N-{2-[1-(6-氯-3-吡啶甲基)-咪唑啉基-乙烯基]-2-硝基-硫酰基}-4-氟-苯甲酰胺)和Ⅳ-2f(N-[1-(6-氯-3-吡啶甲基)-7-硝基-咪唑并异噻唑-乙烯基]-4-氟-苯甲酰胺)在1mg/L的浓度下对孑孓的杀死率为100%；部分化合物对豆蚜表现出中等程度的杀灭活性,其中含氟化合物Ⅳ-3d(N-{1-[N-(6-氯-3-吡啶甲基)-乙胺]-1’-甲胺-2-硝基-乙烯基-硫酰基}-2-氟-苯甲酰胺)和Ⅳ-3m(N-{1-[N-(6-氯-3-吡啶甲基)-乙胺]-1’-甲胺-2-硝基-乙烯基-硫酰基}-3,4-二氟-苯甲酰胺)在500 mg/L浓度下对豆蚜的杀死率为100%,其他大部分的含氟化合物在此浓度下对豆蚜的杀死率可达90%以上。
4.以硝基乙烯基新烟碱类化合物为先导,通过引入第二个强吸电基团将硝基固定为反式构型,设计并合成了14个具有双吸电基团的烟碱类化合物,其中化合物Ⅴ-1a(2-氯-5-(2-硝基-2-腈基-乙烯基-1-咪唑基甲基)-吡啶)在500 mg／L的浓度下对豆蚜的杀死率为100%。
5.根据新的烟碱类杀虫剂与受体的π-π堆积作用方式,设计并合成了31个不含强吸电基团但具有较大共轭体系的烟碱类化合物,并以其为配体把荧光染料中经常使用的强吸电性基团BF2通过配位键的形式引入,设计并合成了24个氟硼烟碱类配位化合物。生物活性测试结果表明,氟硼配合物比其配体具有更高的杀虫和杀菌活性。
As the milestone of the history of insecticides, neonicotinoid insecticides, derived from natural nicotine and shared the same action site as nicotine:nicotinic acetylcholine receptors (nAChR), played an important role in crop protection. Now the development of novel nicotinoid insecticides has been the focus of intense research today because of the resistance to neonicotinoids in some regions. In this thesis five series of novel structure neonicotinoid analogues were designed and synthesized with vinylnitro (iminonitro) neonicotinoid as lead compound. The structure and bioactivity relationships were also studied for seek of lead nicotinoid insecticides.
1. Twenty unsaturated nicotinoid aldoxime compounds were designed and conveniently synthesized by reduction of the corresponding vinylnitro compounds with SnCl2-2H2O. Some evidences from a brief investigation suggest that these aldoximes be formed by reduction of the aci form of nitro, not the usually nitro form. X-ray crystallography analysis reveals that hydroxyl is arranged in trans configuration. Some compounds exhibited diversity of bioactivity with good herbicidal activity, moderate insecticidal activity and weak fungicidal activity.
2. Five trans-nicotinoid aldoxime ether compounds were designed and synthesized with the nicotinoid aldoximes as materials. In addition twelve nicotinoid imidazolyl esters were designed and easily synthesized by internal elimination-rearrangement reaction of the corresponding aldoxime esters with the situ acid catalysis. Some compounds exhibited diversity of bioactivity with moderate herbicidal and insecticidal activity.
3. With vinylnitro neonicotinoids as material, thirty-seven novel neonicotinoids, in which nitro were fixed in cis-configuration by bicycle structure or bulky conjugated system, were designed and synthesized. All the neonicotinoids exhibited excellent insecticidal activities against wiggler and some of them exhibited moderate activities against pea aphids. Compared to nitro-and chloride-containing compounds, fluorine-containing compounds were of higher insecticidal activity.
4. With vinylnitro neonicotinoid as lead compound, fourteen vinylnitro-cyano neonicotinoid analogues were designed and synthesized. X-ray crystallography analysis reveals that nitro is arranged in trans configuration. One of the neonicotinoid analogues exhibited moderate activity against pea aphids.
5. According to theπ-πstacking mode of action of neonicotinoids, thirty-one neonicotinoid analogues with extended conjugated system were designed and synthesized. Further with them as ligands, twenty-four BF2 nicotinoid complexes were designed and synthesized by complexing with BF2. The preliminary bioassay indicated that the BF2 complexes exhibited higher insecticidal and fungicidal activities than their corresponding ligands.
1.以硝基乙烯基新烟碱类化合物为先导,设计并通过还原的方法合成了20个用传统方法难以合成的不饱和烟碱类醛肟化合物。通过实验分析认为,制备此类醛肟的反应是通过还原硝基的酸式结构进行的,而不是通过通常所认为的硝式结构进行的。单晶分析结果显示,醛肟的羟基处于反式结构。此烟碱类醛肟化合物显示出生物活性的多样性,具有较高的除草活性和中等程度的杀虫活性。化合物Ⅱ-2b(1-(5-氯-2-噻唑甲基)-4,5-二氢咪唑-2-甲醛肟)在100 mg／L的浓度下对马唐和鲤肠地下部分的抑制率达到90%以上；化合物Ⅱ-2g(1-(2-噻吩甲基)-4,5-二氢咪唑-2-甲醛肟)在100 mg/L的浓度下对鲤肠地上／地下部分的抑制率均达到80%以上。化合物Ⅱ-2a(1-(6-氯-3-吡啶甲基)-4,5-二氢咪唑-2-甲醛肟)和Ⅱ-2b在50 mg/L的浓度下对孑孓的杀死率可达100%,在500 mg/L的浓度下对豆蚜的杀死率分别为100%和93%。
2.以不饱和烟碱类醛肟为原料,设计并合成了5个含芳香杂环的反式烟碱类肟醚化合物。并利用该烟碱类醛肟与酰氯反应,通过反应中所产生的酸催化相应的肟酯发生分子内消除-重排反应,设计并合成了12个用传统方法难以合成的烟碱类咪唑醇酯化合物。两类烟碱衍生物显示出生物活性的多样性,具有接近中等程度的杀虫和除草活性。其中化合物Ⅲ-2a(2-氯-苯甲酸-1-(6-氯-3-吡啶甲基)-4,5-二氢咪唑基酯)在100 mg/L的浓度下对马唐地上部分的抑制率为50%,地下部分的抑制率为85%。
3.以硝基乙烯基新烟碱类化合物为原料,设计并合成了37个利用共轭体系和双环结构固定硝基为顺式构型的新烟碱类化合物。所有化合物对孑孓表现出良好的杀灭活性,其中Ⅳ-1f(N-{2-[1-(6-氯-3-吡啶甲基)-咪唑啉基-乙烯基]-2-硝基-硫酰基}-4-氟-苯甲酰胺)和Ⅳ-2f(N-[1-(6-氯-3-吡啶甲基)-7-硝基-咪唑并异噻唑-乙烯基]-4-氟-苯甲酰胺)在1mg/L的浓度下对孑孓的杀死率为100%；部分化合物对豆蚜表现出中等程度的杀灭活性,其中含氟化合物Ⅳ-3d(N-{1-[N-(6-氯-3-吡啶甲基)-乙胺]-1’-甲胺-2-硝基-乙烯基-硫酰基}-2-氟-苯甲酰胺)和Ⅳ-3m(N-{1-[N-(6-氯-3-吡啶甲基)-乙胺]-1’-甲胺-2-硝基-乙烯基-硫酰基}-3,4-二氟-苯甲酰胺)在500 mg/L浓度下对豆蚜的杀死率为100%,其他大部分的含氟化合物在此浓度下对豆蚜的杀死率可达90%以上。
4.以硝基乙烯基新烟碱类化合物为先导,通过引入第二个强吸电基团将硝基固定为反式构型,设计并合成了14个具有双吸电基团的烟碱类化合物,其中化合物Ⅴ-1a(2-氯-5-(2-硝基-2-腈基-乙烯基-1-咪唑基甲基)-吡啶)在500 mg／L的浓度下对豆蚜的杀死率为100%。
5.根据新的烟碱类杀虫剂与受体的π-π堆积作用方式,设计并合成了31个不含强吸电基团但具有较大共轭体系的烟碱类化合物,并以其为配体把荧光染料中经常使用的强吸电性基团BF2通过配位键的形式引入,设计并合成了24个氟硼烟碱类配位化合物。生物活性测试结果表明,氟硼配合物比其配体具有更高的杀虫和杀菌活性。
As the milestone of the history of insecticides, neonicotinoid insecticides, derived from natural nicotine and shared the same action site as nicotine:nicotinic acetylcholine receptors (nAChR), played an important role in crop protection. Now the development of novel nicotinoid insecticides has been the focus of intense research today because of the resistance to neonicotinoids in some regions. In this thesis five series of novel structure neonicotinoid analogues were designed and synthesized with vinylnitro (iminonitro) neonicotinoid as lead compound. The structure and bioactivity relationships were also studied for seek of lead nicotinoid insecticides.
1. Twenty unsaturated nicotinoid aldoxime compounds were designed and conveniently synthesized by reduction of the corresponding vinylnitro compounds with SnCl2-2H2O. Some evidences from a brief investigation suggest that these aldoximes be formed by reduction of the aci form of nitro, not the usually nitro form. X-ray crystallography analysis reveals that hydroxyl is arranged in trans configuration. Some compounds exhibited diversity of bioactivity with good herbicidal activity, moderate insecticidal activity and weak fungicidal activity.
2. Five trans-nicotinoid aldoxime ether compounds were designed and synthesized with the nicotinoid aldoximes as materials. In addition twelve nicotinoid imidazolyl esters were designed and easily synthesized by internal elimination-rearrangement reaction of the corresponding aldoxime esters with the situ acid catalysis. Some compounds exhibited diversity of bioactivity with moderate herbicidal and insecticidal activity.
3. With vinylnitro neonicotinoids as material, thirty-seven novel neonicotinoids, in which nitro were fixed in cis-configuration by bicycle structure or bulky conjugated system, were designed and synthesized. All the neonicotinoids exhibited excellent insecticidal activities against wiggler and some of them exhibited moderate activities against pea aphids. Compared to nitro-and chloride-containing compounds, fluorine-containing compounds were of higher insecticidal activity.
4. With vinylnitro neonicotinoid as lead compound, fourteen vinylnitro-cyano neonicotinoid analogues were designed and synthesized. X-ray crystallography analysis reveals that nitro is arranged in trans configuration. One of the neonicotinoid analogues exhibited moderate activity against pea aphids.
5. According to theπ-πstacking mode of action of neonicotinoids, thirty-one neonicotinoid analogues with extended conjugated system were designed and synthesized. Further with them as ligands, twenty-four BF2 nicotinoid complexes were designed and synthesized by complexing with BF2. The preliminary bioassay indicated that the BF2 complexes exhibited higher insecticidal and fungicidal activities than their corresponding ligands.
引文
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