含氮拟除虫菊酯的合成与生物活性
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摘要
拟除虫菊酯为仿生农药，具有高效、低毒、低残留、环境兼容性好等特点，是农药研究和开发的重要方向。本文以拟除虫菊酯乙氰菊酸和功夫菊酸为母体，催化合成了74个新的含酰胺结构的拟除虫菊酯类化合物。对化合物进行了红外光谱、核磁共振氢谱、质谱和元素分析表征，同时对化合物进行了生物活性的研究，并对代表化合物进行了单晶结构的研究。研究内容如下：
1．设计了以对羟基苯乙酸为起始原料合成中间体对乙氧基苯乙酸的新工艺路线，并对工艺条件进行了优化，收率达到90％以上。
设计了以苯乙醚为起始原料，经过Friedel-Crafts反应、Wittig G反应，合成中间体2-对乙氧基苯基丙烯酸乙酯(Ⅳ)的新工艺路线，两步反应收率为63％左右。
选择了以对羟基苯乙酸为起始原料，经过醚化反应、酯化反应、酯缩合反应、羟醛缩合反应、卡宾反应、酯水解反应、缩合反应得到乙氰菊酯的工艺路线，并对工艺条件进行优化，总收率在35％以上。该工艺路线具有原料易得、操作简便、反应条件温和等特点，为乙氰菊酯的开发奠定了一定的基础。
2．分别以1-对乙氧基苯基-2，2-二氯环丙烷甲酸和2，2-二甲基-3-(2-氯-3，3，3-三氟-1-丙烯)环丙烷甲酸为原料，合成得到1-对乙氧基-2，2-二氯环丙烷甲酰基杂环烷(硫)酮类化合物、1-对乙氧基-2，2-二氯环丙烷取代哌啶-1-酮类化合物、1-对乙氧基-2，2-二氯-N-含杂环基环丙烷甲酰胺类化合物、1-对乙氧基-2，2-二氯环丙烷甲酰基杂环烷(硫)酮类化合物、2，2-二甲基-3-(2-氯-3，3，3-三氟-1-丙烯)环丙烷甲酰基杂环烷(硫)酮类化合物和2，2-二甲基-3-(2-氯-3，3，3-三氟-1-丙烯)-N-含杂环基环丙烷甲酰胺类化合物，共37个新化合物；通过对代表性化合物(SⅠ-1-1、SⅡ-2-1、SⅠ-2-1和SⅠ-2-5)的X-射线衍射单晶结构分析，对其结构进行了进一步的确证。
3．分别以1-对乙氧基苯基-2，2-二氯环丙烷甲酸和2，2-二甲基-3-(2-氯-3，3，3-三氟-1-丙烯)环丙烷甲酸为原料，合成得到1-对乙氧基苯基-2，2-二氯-N-(取代苯基)环丙烷甲酰胺类化合物和2，2-二甲基-3-(2-氯-3，3，3-三氟-1-丙烯)-N-取代苯胺环丙烷甲酰胺类化合物，共19个新化合物。
4．1-对乙氧基苯基-2，2-二氯环丙烷甲酸和2，2-二甲基-3-(2-氯-3，3，3-三氟-1-丙烯)环丙烷甲酸为原料，合成得到1-对乙氧基苯基-2，2-二氯环丙烷甲酰-N-取代苯基硫脲类化合物和2，2-二甲基-3-(2-氯-3，3，3-三氟-1-丙烯)环丙烷甲酰-N-取代基硫脲类化合物，共18个新化合物。
5．对以上所合成的化合物进行了初步生物活性(杀虫、杀菌及除草)研究，结果表明，部分化合物对部分供试靶标表现出一定的杀虫抑菌活性，如化合物SⅡ-1-3，在试验浓度下对粘虫的杀虫活性达到90％；SⅡ-4-11、SⅡ-5-9和SⅡ-5-11在试验浓度下，对黄瓜灰霉病菌的防效在65％以上；但所有化合物均没有除草活性。
Pyrethroid belong to bionic pesticide, and they are commonly characterized byhigh efficiency, low toxicity, low residual and good environmental compatibility. Sopyrethroid are important fields of pesticide researching and developing. Seventy-fournovel compounds which are pyrethroid containing amide structure were synthesizedbased on Cycloprothrin acid and Lambda-cyhalothrin acid as the matrix compounds.Their structures were confirmed by IR, ~1HNMR, MS and elemental analysis. The boi-logical activites were studied and the crystal structures of representative compoundswere determined by X-ray diffracttion analysis. It is summarized as follows:
1. A new process of preparing 2-(4-ethoxyphenyl)acetic acid was designed with2-(4-hydroxyphenyl)acetic acid as raw material. The process conditions wereoptimized and the yield is above 90％.
A new process of preparing Ethyl-2-(4-ethoxyphenyl)propenoate was designedwith phenetole as raw material by Friedel-Crafts reaction and Witting G reaction, andthe yield is about 63％.
Cycloprothrin was synthesized from 2-(4-hydroxyphenyl)acetic acid as rawmaterial, by etherification reaction, esterification reaction, ester condensation, aldolcondensation, carbin reaction, ester hydrolyzation and condensation reaction. Theprocess conditions were optimized and the total yield is above 35％. The remarkableadvantages of the route are mild reaction conditions, simple operation, easy obtain ofthe raw materials, etc.
2. 3-(2,2-dichloro-1-(4-ethoxyphenyl)cyclopropanecarbonyl)heterocyclidin-2-(thi)ones, 2,2-dichloro-1-(4-ethoxyphenyl)cyclopropanyl-N-sunsttuted piperidin ket-ones and 2,2-dichloro-1-(4-ethoxyphenyl)-N-heterocyclic cyclopropanecarboxamideswere synthesized from 2,2-dichloro-1-(4-ethoxyphenyl)cyclopropanecarboxylic acid,3-(3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarbonyl) hetero-cyclidin-2-(thi)ones, 3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcycloprop-anyl-N-sunsttuted piperidin ketones and 3-(2-Chloro-3,3,3-trifluoroprop-1-enyl)-2,2- dimethyl-N-heterocyclic cyclopropanecarboxamides were synthesized from 3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarboxylic acid. Compo-unds SⅠ-I-1、SⅡ-2-1、SⅠ-2-1 and SⅠ-2-5 were determined by X-ray diffracttionanalysis.
3. 2,2-Dichloro-1-(4-ethoxyphenyl)-N-sunsttuted phenyl cyclopropanecarbox-amides and 3-(2-Chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethyl-N-sunsttuted phenylcyclopropanecarboxamides were synthesized respectively from 2,2-dichloro-1-(4-ethoxyphenyl)cyclopropanecarboxylic acid and 3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarboxylic acid.
4. 1-(2,2-Dichloro-1-(4-ethoxyphenyl) cyclopropanecarbonyl)-3-sunsttutedphenyl thioureas and 1-(3-(2-Chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclo-propanecarbonyl)-3-sunsttuted phenyl thioureas were synthesized respectively from2,2-dichloro-1-(4-ethoxyphenyl)cyclopropanecarboxylic acid and 3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarboxylic acid.
5. The biological activities(insecticidal activities, fungicidal activities andherbicidal activities) of seventy-four novel compounds were preliminary studied. Theresults showed some compounds exhibited certain insecticidal activities andfungicidal activities, e.g., compound SⅡ-1-3 exhibited 90％inhibition ofMythimnaseparate and compounds SⅡ-4-11, SⅡ-5-9, SⅡ-5-11 exhibited above 65％inhibition of Botrytis cinerea. However, all of them did not exhibite herbicidalactivities.
1．设计了以对羟基苯乙酸为起始原料合成中间体对乙氧基苯乙酸的新工艺路线，并对工艺条件进行了优化，收率达到90％以上。
设计了以苯乙醚为起始原料，经过Friedel-Crafts反应、Wittig G反应，合成中间体2-对乙氧基苯基丙烯酸乙酯(Ⅳ)的新工艺路线，两步反应收率为63％左右。
选择了以对羟基苯乙酸为起始原料，经过醚化反应、酯化反应、酯缩合反应、羟醛缩合反应、卡宾反应、酯水解反应、缩合反应得到乙氰菊酯的工艺路线，并对工艺条件进行优化，总收率在35％以上。该工艺路线具有原料易得、操作简便、反应条件温和等特点，为乙氰菊酯的开发奠定了一定的基础。
2．分别以1-对乙氧基苯基-2，2-二氯环丙烷甲酸和2，2-二甲基-3-(2-氯-3，3，3-三氟-1-丙烯)环丙烷甲酸为原料，合成得到1-对乙氧基-2，2-二氯环丙烷甲酰基杂环烷(硫)酮类化合物、1-对乙氧基-2，2-二氯环丙烷取代哌啶-1-酮类化合物、1-对乙氧基-2，2-二氯-N-含杂环基环丙烷甲酰胺类化合物、1-对乙氧基-2，2-二氯环丙烷甲酰基杂环烷(硫)酮类化合物、2，2-二甲基-3-(2-氯-3，3，3-三氟-1-丙烯)环丙烷甲酰基杂环烷(硫)酮类化合物和2，2-二甲基-3-(2-氯-3，3，3-三氟-1-丙烯)-N-含杂环基环丙烷甲酰胺类化合物，共37个新化合物；通过对代表性化合物(SⅠ-1-1、SⅡ-2-1、SⅠ-2-1和SⅠ-2-5)的X-射线衍射单晶结构分析，对其结构进行了进一步的确证。
3．分别以1-对乙氧基苯基-2，2-二氯环丙烷甲酸和2，2-二甲基-3-(2-氯-3，3，3-三氟-1-丙烯)环丙烷甲酸为原料，合成得到1-对乙氧基苯基-2，2-二氯-N-(取代苯基)环丙烷甲酰胺类化合物和2，2-二甲基-3-(2-氯-3，3，3-三氟-1-丙烯)-N-取代苯胺环丙烷甲酰胺类化合物，共19个新化合物。
4．1-对乙氧基苯基-2，2-二氯环丙烷甲酸和2，2-二甲基-3-(2-氯-3，3，3-三氟-1-丙烯)环丙烷甲酸为原料，合成得到1-对乙氧基苯基-2，2-二氯环丙烷甲酰-N-取代苯基硫脲类化合物和2，2-二甲基-3-(2-氯-3，3，3-三氟-1-丙烯)环丙烷甲酰-N-取代基硫脲类化合物，共18个新化合物。
5．对以上所合成的化合物进行了初步生物活性(杀虫、杀菌及除草)研究，结果表明，部分化合物对部分供试靶标表现出一定的杀虫抑菌活性，如化合物SⅡ-1-3，在试验浓度下对粘虫的杀虫活性达到90％；SⅡ-4-11、SⅡ-5-9和SⅡ-5-11在试验浓度下，对黄瓜灰霉病菌的防效在65％以上；但所有化合物均没有除草活性。
Pyrethroid belong to bionic pesticide, and they are commonly characterized byhigh efficiency, low toxicity, low residual and good environmental compatibility. Sopyrethroid are important fields of pesticide researching and developing. Seventy-fournovel compounds which are pyrethroid containing amide structure were synthesizedbased on Cycloprothrin acid and Lambda-cyhalothrin acid as the matrix compounds.Their structures were confirmed by IR, ~1HNMR, MS and elemental analysis. The boi-logical activites were studied and the crystal structures of representative compoundswere determined by X-ray diffracttion analysis. It is summarized as follows:
1. A new process of preparing 2-(4-ethoxyphenyl)acetic acid was designed with2-(4-hydroxyphenyl)acetic acid as raw material. The process conditions wereoptimized and the yield is above 90％.
A new process of preparing Ethyl-2-(4-ethoxyphenyl)propenoate was designedwith phenetole as raw material by Friedel-Crafts reaction and Witting G reaction, andthe yield is about 63％.
Cycloprothrin was synthesized from 2-(4-hydroxyphenyl)acetic acid as rawmaterial, by etherification reaction, esterification reaction, ester condensation, aldolcondensation, carbin reaction, ester hydrolyzation and condensation reaction. Theprocess conditions were optimized and the total yield is above 35％. The remarkableadvantages of the route are mild reaction conditions, simple operation, easy obtain ofthe raw materials, etc.
2. 3-(2,2-dichloro-1-(4-ethoxyphenyl)cyclopropanecarbonyl)heterocyclidin-2-(thi)ones, 2,2-dichloro-1-(4-ethoxyphenyl)cyclopropanyl-N-sunsttuted piperidin ket-ones and 2,2-dichloro-1-(4-ethoxyphenyl)-N-heterocyclic cyclopropanecarboxamideswere synthesized from 2,2-dichloro-1-(4-ethoxyphenyl)cyclopropanecarboxylic acid,3-(3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarbonyl) hetero-cyclidin-2-(thi)ones, 3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcycloprop-anyl-N-sunsttuted piperidin ketones and 3-(2-Chloro-3,3,3-trifluoroprop-1-enyl)-2,2- dimethyl-N-heterocyclic cyclopropanecarboxamides were synthesized from 3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarboxylic acid. Compo-unds SⅠ-I-1、SⅡ-2-1、SⅠ-2-1 and SⅠ-2-5 were determined by X-ray diffracttionanalysis.
3. 2,2-Dichloro-1-(4-ethoxyphenyl)-N-sunsttuted phenyl cyclopropanecarbox-amides and 3-(2-Chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethyl-N-sunsttuted phenylcyclopropanecarboxamides were synthesized respectively from 2,2-dichloro-1-(4-ethoxyphenyl)cyclopropanecarboxylic acid and 3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarboxylic acid.
4. 1-(2,2-Dichloro-1-(4-ethoxyphenyl) cyclopropanecarbonyl)-3-sunsttutedphenyl thioureas and 1-(3-(2-Chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclo-propanecarbonyl)-3-sunsttuted phenyl thioureas were synthesized respectively from2,2-dichloro-1-(4-ethoxyphenyl)cyclopropanecarboxylic acid and 3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarboxylic acid.
5. The biological activities(insecticidal activities, fungicidal activities andherbicidal activities) of seventy-four novel compounds were preliminary studied. Theresults showed some compounds exhibited certain insecticidal activities andfungicidal activities, e.g., compound SⅡ-1-3 exhibited 90％inhibition ofMythimnaseparate and compounds SⅡ-4-11, SⅡ-5-9, SⅡ-5-11 exhibited above 65％inhibition of Botrytis cinerea. However, all of them did not exhibite herbicidalactivities.
引文
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