几种蛀果害虫性信息素的合成与应用研究
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摘要
利用信息素防控害虫是一种理想的害物综合治理措施，这一技术对农业有害生物无公害防治具有重大意义。昆虫信息素成分的鉴定和应用技术研究都离不开立体结构确定的纯化合物，因此改进这类物质的合成工艺，发展高效的合成方法，以获得高纯度的信息素化合物，是昆虫信息素研究领域的重要课题。已知的昆虫性信息素组分中，有75%以上是具有10-18个碳的直链不饱和醇及其衍生物。这类化合物虽然结构简单，但已有的合成方法普遍存在产率低、产物立体异构体难于分离等缺点，严重影响了此类新农药的应用。
本研究以廉价易得的常见试剂为原料，通过Wittig反应和Coupling反应合成了苹果蠹蛾、大豆食心虫等蛀果害虫性信息素在内的23种性信息素类化合物，其中17种为直链烯醇，6种为直链烯醇乙酸酯。建立了立体选择性合成烯醇类昆虫性信息素化合物的通用方法。以合成化合物为引诱剂，对苹果蠹蛾、大豆食心虫等几种蛀果害虫进行了田间引诱活性测试；在田间试验基础上，探讨了苹果蠹蛾、大豆食心虫性信息素化合物的引诱活性及田间应用技术。并对核桃举肢蛾雌性信息素、小檗绢粉蝶引诱剂进行了初步的研究。主要研究结论摘要如下：
1.以α,ω-二醇为起始原料，氢溴酸选择性单溴代合成了ω-溴代醇，ω-溴代醇与三苯基膦反应所得的季鏻盐继续与适当的脂肪醛发生Wittig反应，获得了6种直链烯醇，4种烯醇酯，共10种性信息素化合物。其中化合物9-十六碳烯-1-醇、8-十三碳烯-1-醇、6-十三碳烯-1-醇及其酯，和10-十六碳烯-1-醇、8-十二碳烯-1-醇都以Z式为主；而E,E-8,10-十二碳二烯-1-醇及其酯则以E式为主。考察了α,ω-二醇单溴代反应的影响因素，获得的ω-溴代醇产率高于87%，单溴代率达95%以上。考察了碱的种类、用量、中间体反应温度及溶剂等因素对活泼ylide参与的Wittig反应产率和立体化学的影响。总结出了通过活泼ylide中间体获得主产物为Z、E式烯醇的不同实验条件。
2.将ω-溴代醇羟基用2,3-二氢吡喃保护后与Mg反应制成格氏试剂BrMg(CH2)nOTHP；在CuLi2Cl4催化下，格氏试剂与几种烯醇酯偶联、水解，得到了的E-8-十二碳烯-1-醇、E,E-8,10-十二碳二烯-1-醇、E-10-十二碳烯-1-醇、E,E-10,12-十四碳二烯-1-醇、E-10-十四碳烯-1-醇、E-11-十三碳烯-1-醇、E-12-十六碳烯-1-醇、E,E-12,14-十六碳二烯-1-醇等8种立体结构确定的烯醇和一种烯醇酯，立体异构体含量高于95%，反应总收率可达50%以上。对上述条件下不反应的Z-3-己烯-1-醇乙酸酯，通过加入N-甲基吡咯烷酮顺利实现偶联，获得Z-9-十二碳烯-1-醇、Z-11-十四碳烯-1-醇、Z-12-十五碳烯-1-醇、Z-13-十六碳烯-1-醇等4种Z-式烯醇。
3.在田间测试了E-10-十二碳烯-1-醇乙酸酯、E,E-8,10-十二碳二烯-1-醇乙酸酯、E-8-十二碳烯-1-醇乙酸酯、E,E-8,10-十二碳二烯-1-醇、E-10-十二碳烯-1-醇、E-8-十二碳烯-1-醇、Z-9-十二碳烯-1-醇等7种候选化合物对大豆食心虫的引诱活性。结果表明，E-10-十二碳烯-1-醇乙酸酯具有明显的引诱活性。当用E-10-十二碳烯-1-醇乙酸酯剂量为0.1mg/诱芯时田间引诱活性较好。
4.通过田间试验测试了E,E-8,10-十二碳二烯-1-醇对苹果蠹蛾的引诱活性，探索了不同剂量、不同诱捕器悬挂高度对诱捕效果的影响。结果表明在0.25-2.00mg/诱芯的剂量范围内，以0.75mg/诱芯对苹果蠹蛾雄蛾的引诱活性最佳。诱捕器的悬挂高度以设置于树高的4/5处引诱效果最好。
5.通过对核桃举肢蛾性信息素候选化合物Z-9-十六碳烯-1-醇、Z-9-十六碳烯-1-醇乙酸酯、Z-8-十三碳烯-1-醇、Z-8-十三碳烯-1-醇乙酸酯的活性测试，发现所有供试化合物对核桃举肢蛾雄虫均没有明显的引诱活性。进一步对核桃举肢蛾进行了生物学及性信息素化学研究，研究表明核桃举肢蛾在室内有性兴奋现象但无交配行为。对兴奋期的雌蛾腺体溶剂提取物的GC-MS分析表明，提取物中含有两种可能的性信息素组分，其结构为十六碳烯醇、十六碳烯醇乙酸酯，但双键位置及构型尚未确定。
6.试验中发现了对小檗绢粉蝶雄蝶具有明显引诱活性的化合物组合。化合物Z-9-十六碳烯-1-醇和Z-8-十三碳烯-1-醇乙酸酯组成的诱芯，对小檗绢粉蝶雄虫具有很强的引诱活性，当二者以7:3的比例混合时引诱效果尤其显著。
本论文对传统的直链烯醇类昆虫性信息素合成方法进行了探索，总结了Wittig反应条件对产物立体构型的影响；对偶联法合成此类物质进行了方法改进，拓展了此反应的适用范围，使Coupling反应成为普遍适用的合成烯醇类昆虫性信息素的通用方法。为烯醇类昆虫性信息素化合物的实验室合成、小批量生产提供了科学依据；为利用性信息素防治苹果蠹蛾及大豆食心虫奠定了基础；也为核桃举肢蛾雌性信息素、小檗绢粉蝶引诱剂研究提供了科学依据，上述研究结果对于利用昆虫性信息素防治蛀果害虫的产品和技术开发具有一定的理论和应用价值。
The use of sex pheromones to control target pests is an ideal measures to Intergrated Pests Management-IPM, Furthermore, this technology is of great significance for the harmlessly controlling pests. The structural identifications and practical applications of sex pheromones usually require stereoisomeric pure compounds. Therefore, it's very vital to ameliorate the synthetic pathways, develop high efficient synthetic methods to obtain the highly pure organic compounds in pheromone research fields. To date, more than75%Lepidopteran sex pheromones components are composed of C10-C18unsaturated straight-chain fatty alcohols and their derivatives. Although the structures of these compounds are simple, the existing synthetic methods have some drawbacks such as low yields, hard to separate the isomers, which confined the application of this new pesticide.
In this thesis, cheap and commercially available compounds as starting materials, the pheromones of Leguminivora glycin ivorella M., Laspeyresia pomonella L. and some analogues including17long chain ene alcohols and6linear ene alcohol acetates were synthesized by Wittig reaction or Cross-coupling reaction. And the general stereoselective synthetic methods to this kind of ene alcohols were established.
The attractive activities of synthetic compounds to Laspeyresia pomonella L, Leguminivora glycinivorella M and other fruit boring pests were tested in the field. On the basis of field trap test, the attractive activities and applied technologies of Leguminivora glycin ivorella M., Laspeyresia pomonella L's sex pheromones were explored too. At the same time, the sex pheromones of Atrijuglans hetaohei Yang and Aporia hippia Bremer's attractants were also be investigated. Following are the main results.
1. Starting from the cheap commercially available starting materials a, co-diols, using HBr to region-selectively brominated to give co-bromoalkan-1-ol, followed the addition of triphenylphosphine to obtain tetrabutalphosphine salt. After deprotonation, the ylide reacted with appropriate aliphatic aldehyde and produced compounds9-16:OH,10-16:OH,8-13: OH,6-13:OH,8-12:OH with dominantly Z-stereoselectivity and E,E-8,10-12:OH with mainly E-stereoselectivity. In above mentioned synthetic process, the factors were studied in bromination and Wittig reaction, which may be influence the yields, especially applying different types of bases, solvents. The co-bromoalkan-1-ols were prepared via region-selectively brominated a co-diols in89%, and above95%region-selectively. In addition, the factors influencing on the product yield and stereoselectivity were investigated, such as the species and quantities of alkalis, the temperature of intermediates, the solvents and so on. Effect of various reaction conditions on the Wittig reaction of aldehydes with unstabilized phosphine ylide salts to get main Z/E-isomers of products was considered.
2. ω-Bromoalkan-1-ols were protected by DHP and then reacted with Mg to prepare Grignard reagent BrMg(CH2)nOTHP, continued to Cross coupling reaction with different ene-ol acetates, ultimately afforded compounds E-8-12:OH、E,E-8,10-12:OH、E-10-12: OH、E,E-10,12-14:OH、E-10-14:OH、E-11-13:OH、E-12-16:OH、E,E-12,14-16: OH with95%E conformation in above50%overall yield. Especially for Z-9-12:OH、 Z-11-14:OH、Z-12-15:OH、Z-13-16:OH, the solvent was changed to NMP to give the target molecules with Z isomer.
3. The attractive activities of seven candidates of E-10-12:Ac, E, E-8,10-12:Ac, E-8-12:Ac, E,E-8,10-12:OH, E-10-12:OH, E-8-12:OH, Z-9-12:OH to Leguminivora glycinivorella M were performed through field trap test. The result showed that E-10-12:Ac has the greatest attraction to Leguminivora glycinivorella M, and the most effective dosage should be less than0.1mg/trap.
4. The attractive activity of E,E-8,10-12:OH to Laspeyresia pomonella L, was tested in the field. Trapping efficiency with different dose of sex pheromone and different hanging height of traps were discussed. The result showed that0.75mg/trap has the greatest attraction to Laspeyresia pomonella L within the range of0.25-2.00mg/trap and the most suitable hanging height of traps was on the4/5part of orchard.
5. Candidate compounds were synthesized as Atrijuglans hetaohei Yang's sex pheromone components, such as Z-8-13:Ac, Z-9-16:OH, through Wittig reaction. To our surprise, all synthetic compounds didn't show attractive activities at all. Through biological and chemical indoor experiments, the result showed that the Atrijuglans hetaohei Yang has sexual excitement but without mating. After analysis of the sexual glands of Atrijuglans hetaohei Yang by GC-MS, it contained C16ene-ol、C16ene-ol acetate, but the position of double bond and its geometry couldn't be confirmed.
6. When the lure of Z-9-16:OH and Z-8-13:Ac to Atrijuglans hetaohei Yang were performed in the field, pleasingly, the lure showed attractive activities to the male Aporia hippia Bremer. Further testing showed that the attractive activity is strongest when the ratio of Z-9-16:OH and Z-8-13:OAc is7:3. This is the first report of the attractant about Aporia hippia Bremer.
In conclusion, we present a general synthetic procedure to prepare the linear ene-ol sex pheromones in high yield and high stereoselectivity. Furthermore, the ideal attractants against Laspeyresia pomonella L and Leguminivora glycinivorella M. as well as the attractive technology in the field were provided. Last but not least, we preliminary researched the sex pheromones for Atrijuglans hetaohei Yang and the attractant of Aporia hippia Bxemer. It is the first time to carry out the attractant of Aporia hippia Bremer. These results are meaningful to controlling pests of crops and the development of agriculture.
本研究以廉价易得的常见试剂为原料，通过Wittig反应和Coupling反应合成了苹果蠹蛾、大豆食心虫等蛀果害虫性信息素在内的23种性信息素类化合物，其中17种为直链烯醇，6种为直链烯醇乙酸酯。建立了立体选择性合成烯醇类昆虫性信息素化合物的通用方法。以合成化合物为引诱剂，对苹果蠹蛾、大豆食心虫等几种蛀果害虫进行了田间引诱活性测试；在田间试验基础上，探讨了苹果蠹蛾、大豆食心虫性信息素化合物的引诱活性及田间应用技术。并对核桃举肢蛾雌性信息素、小檗绢粉蝶引诱剂进行了初步的研究。主要研究结论摘要如下：
1.以α,ω-二醇为起始原料，氢溴酸选择性单溴代合成了ω-溴代醇，ω-溴代醇与三苯基膦反应所得的季鏻盐继续与适当的脂肪醛发生Wittig反应，获得了6种直链烯醇，4种烯醇酯，共10种性信息素化合物。其中化合物9-十六碳烯-1-醇、8-十三碳烯-1-醇、6-十三碳烯-1-醇及其酯，和10-十六碳烯-1-醇、8-十二碳烯-1-醇都以Z式为主；而E,E-8,10-十二碳二烯-1-醇及其酯则以E式为主。考察了α,ω-二醇单溴代反应的影响因素，获得的ω-溴代醇产率高于87%，单溴代率达95%以上。考察了碱的种类、用量、中间体反应温度及溶剂等因素对活泼ylide参与的Wittig反应产率和立体化学的影响。总结出了通过活泼ylide中间体获得主产物为Z、E式烯醇的不同实验条件。
2.将ω-溴代醇羟基用2,3-二氢吡喃保护后与Mg反应制成格氏试剂BrMg(CH2)nOTHP；在CuLi2Cl4催化下，格氏试剂与几种烯醇酯偶联、水解，得到了的E-8-十二碳烯-1-醇、E,E-8,10-十二碳二烯-1-醇、E-10-十二碳烯-1-醇、E,E-10,12-十四碳二烯-1-醇、E-10-十四碳烯-1-醇、E-11-十三碳烯-1-醇、E-12-十六碳烯-1-醇、E,E-12,14-十六碳二烯-1-醇等8种立体结构确定的烯醇和一种烯醇酯，立体异构体含量高于95%，反应总收率可达50%以上。对上述条件下不反应的Z-3-己烯-1-醇乙酸酯，通过加入N-甲基吡咯烷酮顺利实现偶联，获得Z-9-十二碳烯-1-醇、Z-11-十四碳烯-1-醇、Z-12-十五碳烯-1-醇、Z-13-十六碳烯-1-醇等4种Z-式烯醇。
3.在田间测试了E-10-十二碳烯-1-醇乙酸酯、E,E-8,10-十二碳二烯-1-醇乙酸酯、E-8-十二碳烯-1-醇乙酸酯、E,E-8,10-十二碳二烯-1-醇、E-10-十二碳烯-1-醇、E-8-十二碳烯-1-醇、Z-9-十二碳烯-1-醇等7种候选化合物对大豆食心虫的引诱活性。结果表明，E-10-十二碳烯-1-醇乙酸酯具有明显的引诱活性。当用E-10-十二碳烯-1-醇乙酸酯剂量为0.1mg/诱芯时田间引诱活性较好。
4.通过田间试验测试了E,E-8,10-十二碳二烯-1-醇对苹果蠹蛾的引诱活性，探索了不同剂量、不同诱捕器悬挂高度对诱捕效果的影响。结果表明在0.25-2.00mg/诱芯的剂量范围内，以0.75mg/诱芯对苹果蠹蛾雄蛾的引诱活性最佳。诱捕器的悬挂高度以设置于树高的4/5处引诱效果最好。
5.通过对核桃举肢蛾性信息素候选化合物Z-9-十六碳烯-1-醇、Z-9-十六碳烯-1-醇乙酸酯、Z-8-十三碳烯-1-醇、Z-8-十三碳烯-1-醇乙酸酯的活性测试，发现所有供试化合物对核桃举肢蛾雄虫均没有明显的引诱活性。进一步对核桃举肢蛾进行了生物学及性信息素化学研究，研究表明核桃举肢蛾在室内有性兴奋现象但无交配行为。对兴奋期的雌蛾腺体溶剂提取物的GC-MS分析表明，提取物中含有两种可能的性信息素组分，其结构为十六碳烯醇、十六碳烯醇乙酸酯，但双键位置及构型尚未确定。
6.试验中发现了对小檗绢粉蝶雄蝶具有明显引诱活性的化合物组合。化合物Z-9-十六碳烯-1-醇和Z-8-十三碳烯-1-醇乙酸酯组成的诱芯，对小檗绢粉蝶雄虫具有很强的引诱活性，当二者以7:3的比例混合时引诱效果尤其显著。
本论文对传统的直链烯醇类昆虫性信息素合成方法进行了探索，总结了Wittig反应条件对产物立体构型的影响；对偶联法合成此类物质进行了方法改进，拓展了此反应的适用范围，使Coupling反应成为普遍适用的合成烯醇类昆虫性信息素的通用方法。为烯醇类昆虫性信息素化合物的实验室合成、小批量生产提供了科学依据；为利用性信息素防治苹果蠹蛾及大豆食心虫奠定了基础；也为核桃举肢蛾雌性信息素、小檗绢粉蝶引诱剂研究提供了科学依据，上述研究结果对于利用昆虫性信息素防治蛀果害虫的产品和技术开发具有一定的理论和应用价值。
The use of sex pheromones to control target pests is an ideal measures to Intergrated Pests Management-IPM, Furthermore, this technology is of great significance for the harmlessly controlling pests. The structural identifications and practical applications of sex pheromones usually require stereoisomeric pure compounds. Therefore, it's very vital to ameliorate the synthetic pathways, develop high efficient synthetic methods to obtain the highly pure organic compounds in pheromone research fields. To date, more than75%Lepidopteran sex pheromones components are composed of C10-C18unsaturated straight-chain fatty alcohols and their derivatives. Although the structures of these compounds are simple, the existing synthetic methods have some drawbacks such as low yields, hard to separate the isomers, which confined the application of this new pesticide.
In this thesis, cheap and commercially available compounds as starting materials, the pheromones of Leguminivora glycin ivorella M., Laspeyresia pomonella L. and some analogues including17long chain ene alcohols and6linear ene alcohol acetates were synthesized by Wittig reaction or Cross-coupling reaction. And the general stereoselective synthetic methods to this kind of ene alcohols were established.
The attractive activities of synthetic compounds to Laspeyresia pomonella L, Leguminivora glycinivorella M and other fruit boring pests were tested in the field. On the basis of field trap test, the attractive activities and applied technologies of Leguminivora glycin ivorella M., Laspeyresia pomonella L's sex pheromones were explored too. At the same time, the sex pheromones of Atrijuglans hetaohei Yang and Aporia hippia Bremer's attractants were also be investigated. Following are the main results.
1. Starting from the cheap commercially available starting materials a, co-diols, using HBr to region-selectively brominated to give co-bromoalkan-1-ol, followed the addition of triphenylphosphine to obtain tetrabutalphosphine salt. After deprotonation, the ylide reacted with appropriate aliphatic aldehyde and produced compounds9-16:OH,10-16:OH,8-13: OH,6-13:OH,8-12:OH with dominantly Z-stereoselectivity and E,E-8,10-12:OH with mainly E-stereoselectivity. In above mentioned synthetic process, the factors were studied in bromination and Wittig reaction, which may be influence the yields, especially applying different types of bases, solvents. The co-bromoalkan-1-ols were prepared via region-selectively brominated a co-diols in89%, and above95%region-selectively. In addition, the factors influencing on the product yield and stereoselectivity were investigated, such as the species and quantities of alkalis, the temperature of intermediates, the solvents and so on. Effect of various reaction conditions on the Wittig reaction of aldehydes with unstabilized phosphine ylide salts to get main Z/E-isomers of products was considered.
2. ω-Bromoalkan-1-ols were protected by DHP and then reacted with Mg to prepare Grignard reagent BrMg(CH2)nOTHP, continued to Cross coupling reaction with different ene-ol acetates, ultimately afforded compounds E-8-12:OH、E,E-8,10-12:OH、E-10-12: OH、E,E-10,12-14:OH、E-10-14:OH、E-11-13:OH、E-12-16:OH、E,E-12,14-16: OH with95%E conformation in above50%overall yield. Especially for Z-9-12:OH、 Z-11-14:OH、Z-12-15:OH、Z-13-16:OH, the solvent was changed to NMP to give the target molecules with Z isomer.
3. The attractive activities of seven candidates of E-10-12:Ac, E, E-8,10-12:Ac, E-8-12:Ac, E,E-8,10-12:OH, E-10-12:OH, E-8-12:OH, Z-9-12:OH to Leguminivora glycinivorella M were performed through field trap test. The result showed that E-10-12:Ac has the greatest attraction to Leguminivora glycinivorella M, and the most effective dosage should be less than0.1mg/trap.
4. The attractive activity of E,E-8,10-12:OH to Laspeyresia pomonella L, was tested in the field. Trapping efficiency with different dose of sex pheromone and different hanging height of traps were discussed. The result showed that0.75mg/trap has the greatest attraction to Laspeyresia pomonella L within the range of0.25-2.00mg/trap and the most suitable hanging height of traps was on the4/5part of orchard.
5. Candidate compounds were synthesized as Atrijuglans hetaohei Yang's sex pheromone components, such as Z-8-13:Ac, Z-9-16:OH, through Wittig reaction. To our surprise, all synthetic compounds didn't show attractive activities at all. Through biological and chemical indoor experiments, the result showed that the Atrijuglans hetaohei Yang has sexual excitement but without mating. After analysis of the sexual glands of Atrijuglans hetaohei Yang by GC-MS, it contained C16ene-ol、C16ene-ol acetate, but the position of double bond and its geometry couldn't be confirmed.
6. When the lure of Z-9-16:OH and Z-8-13:Ac to Atrijuglans hetaohei Yang were performed in the field, pleasingly, the lure showed attractive activities to the male Aporia hippia Bremer. Further testing showed that the attractive activity is strongest when the ratio of Z-9-16:OH and Z-8-13:OAc is7:3. This is the first report of the attractant about Aporia hippia Bremer.
In conclusion, we present a general synthetic procedure to prepare the linear ene-ol sex pheromones in high yield and high stereoselectivity. Furthermore, the ideal attractants against Laspeyresia pomonella L and Leguminivora glycinivorella M. as well as the attractive technology in the field were provided. Last but not least, we preliminary researched the sex pheromones for Atrijuglans hetaohei Yang and the attractant of Aporia hippia Bxemer. It is the first time to carry out the attractant of Aporia hippia Bremer. These results are meaningful to controlling pests of crops and the development of agriculture.
引文
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