新型邻二酰胺类化合物的合成及其杀虫活性研究
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摘要
21世纪的农药必须具有高效、安全、经济、环境友好的特点。近期发现的新型邻甲酰氨基苯甲酰胺类和邻苯二甲酰胺类是两类广谱的杀虫剂,其独特的杀虫机制可保证动物之间的良好选择性,且与传统杀虫剂无交互抗性,具有十分广阔的发展前景。
本文综述了杀虫剂和鱼尼丁受体杀虫剂的最新研究进展,详细介绍了两类杀虫剂的创制经纬、品种和作用机理,并以氯虫酰胺和氟虫酰胺为先导化合物,采用“亚结构连接法”、“生物电子等排”等类同合成途径设计并成功合成了共53个新化合物。合成的目标化合物按结构可分为以下四类:
(1)5-氯-N-取代苯基-1-取代基-3-甲基-1H-吡唑-4-甲酰胺类化合物Ⅰ:
(2)4-氯-N-取代苯基-1-取代基-3-乙基-1H-吡唑-5-甲酰胺类化合物Ⅱ:
(3)7-(3-溴-1-(3-氯吡啶-2-基)-1H-吡唑-5-甲酰胺基)-2,4-二取代-N-异丙基-3-氧-3,4-二氢-2H-苯并[b][1,4]噁嗪-6-甲酰胺类化合物Ⅲ:
(4)N-异丙基-N-杂环取代邻苯二甲酰胺类化合物Ⅳ:
对各类中间体和目标化合物的合成条件进行了较为详细的探讨,对所有目标化合物进行了纯化并采用IR、~1H NMR、LC/MS等进行了表征。
部分目标化合物已经进行了生物活性测试。化合物Ⅰ、Ⅲ和Ⅳ表现出不同程度的杀虫活性,如在所测浓度下,化合物Ⅰa和Ⅰt对蚜虫有B级杀虫活性(>70%的死亡率),化合物Ⅰq、Ⅰt和Ⅰv对叶蝉有B级杀虫活性,化合物Ⅲn对粘虫有B级杀虫活性。
In the 21~(th) century, pesticide must have the characteristics of high effect, safety, low cost and environmentally-friend. The novel anthranilic diamides and phthalic diamides found recently are two kinds of broad-spectrum insecticides, which will be found a wider application because their unique insecticide mechanism can ensure very good selectivity between animals and they have no cross resistance with traditional insecticides.
The latest research development of insecticides and ryanodine receptor insecticides were reviewed in this thesis, the involvement of discovery, varieties and mechanism of the two kinds of insecticides were introduced in detail. On basis of the structures of the lead compounds chlorantraniliprole and flubendiamide, 53 new compounds were synthesized by anologue synthesis designing principles such as sub-structure linkage and bioisosterism. According to their structures, these compounds can be divided into four series as followings:
(1) 5-chloro-N-substitutedphenyl-1-substituted-3-methyl-1H-pyrazo le-4-carboxamidesⅠ:
(2) 4-chloro-N-substitutedphenyl-1-substituted-3-ethyl- 1H-pyrazole5-carboxamidesⅡ:
(3) 7-(3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamid o)-2,4-disubstituted-N-isopropyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxa zine-6-carboxamidesⅢ:
(4) N-isopropyl-N-heterophthalic diamidesⅣ:
Synthesis methods for each intermediates and target compounds were studied, and the structures of the prepared compounds were confirmed by IR, ~1H NMR and LC/MS.
Part of target compounds have been tested. CompoundsⅠ,ⅢandⅣexhibited different extent of insecticidal efficacy, for example,Ⅰa and It exhibited B insecticidal activity( >70% mortality rate) against Aphis fabae,Ⅰq,Ⅰt andⅠv had B insecticidal activity against Nephotettix cincticeps,Ⅲn showed B insecticidal activity against Mythimna separate at the concentration.
本文综述了杀虫剂和鱼尼丁受体杀虫剂的最新研究进展,详细介绍了两类杀虫剂的创制经纬、品种和作用机理,并以氯虫酰胺和氟虫酰胺为先导化合物,采用“亚结构连接法”、“生物电子等排”等类同合成途径设计并成功合成了共53个新化合物。合成的目标化合物按结构可分为以下四类:
(1)5-氯-N-取代苯基-1-取代基-3-甲基-1H-吡唑-4-甲酰胺类化合物Ⅰ:
(2)4-氯-N-取代苯基-1-取代基-3-乙基-1H-吡唑-5-甲酰胺类化合物Ⅱ:
(3)7-(3-溴-1-(3-氯吡啶-2-基)-1H-吡唑-5-甲酰胺基)-2,4-二取代-N-异丙基-3-氧-3,4-二氢-2H-苯并[b][1,4]噁嗪-6-甲酰胺类化合物Ⅲ:
(4)N-异丙基-N-杂环取代邻苯二甲酰胺类化合物Ⅳ:
对各类中间体和目标化合物的合成条件进行了较为详细的探讨,对所有目标化合物进行了纯化并采用IR、~1H NMR、LC/MS等进行了表征。
部分目标化合物已经进行了生物活性测试。化合物Ⅰ、Ⅲ和Ⅳ表现出不同程度的杀虫活性,如在所测浓度下,化合物Ⅰa和Ⅰt对蚜虫有B级杀虫活性(>70%的死亡率),化合物Ⅰq、Ⅰt和Ⅰv对叶蝉有B级杀虫活性,化合物Ⅲn对粘虫有B级杀虫活性。
In the 21~(th) century, pesticide must have the characteristics of high effect, safety, low cost and environmentally-friend. The novel anthranilic diamides and phthalic diamides found recently are two kinds of broad-spectrum insecticides, which will be found a wider application because their unique insecticide mechanism can ensure very good selectivity between animals and they have no cross resistance with traditional insecticides.
The latest research development of insecticides and ryanodine receptor insecticides were reviewed in this thesis, the involvement of discovery, varieties and mechanism of the two kinds of insecticides were introduced in detail. On basis of the structures of the lead compounds chlorantraniliprole and flubendiamide, 53 new compounds were synthesized by anologue synthesis designing principles such as sub-structure linkage and bioisosterism. According to their structures, these compounds can be divided into four series as followings:
(1) 5-chloro-N-substitutedphenyl-1-substituted-3-methyl-1H-pyrazo le-4-carboxamidesⅠ:
(2) 4-chloro-N-substitutedphenyl-1-substituted-3-ethyl- 1H-pyrazole5-carboxamidesⅡ:
(3) 7-(3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamid o)-2,4-disubstituted-N-isopropyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxa zine-6-carboxamidesⅢ:
(4) N-isopropyl-N-heterophthalic diamidesⅣ:
Synthesis methods for each intermediates and target compounds were studied, and the structures of the prepared compounds were confirmed by IR, ~1H NMR and LC/MS.
Part of target compounds have been tested. CompoundsⅠ,ⅢandⅣexhibited different extent of insecticidal efficacy, for example,Ⅰa and It exhibited B insecticidal activity( >70% mortality rate) against Aphis fabae,Ⅰq,Ⅰt andⅠv had B insecticidal activity against Nephotettix cincticeps,Ⅲn showed B insecticidal activity against Mythimna separate at the concentration.
引文
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