【摘要】 【背景】近年来，随着新引种作物藜麦种植面积的显著增长，取食藜属植物的宽胫夜蛾（Protoschinia scutosa）逐渐增多并成为危害藜麦的主要害虫，对我国农作物生产构成潜在威胁。【目的】通过对宽胫夜蛾性信息素组分母体结构顺-11-十六碳烯乙酸酯（Z11-16:Ac）极性基团修饰，设计合成两种不同类型的类似物，并对其生物活性进行测定，为利用性信息素及类似物绿色防控宽胫夜蛾提供理论依据。【方法】以性信息素前体顺-11-十六碳烯醇（Z11-16:OH）为原料，三乙胺作缚酸剂（与酸酐反应时需加入催化剂 4-二甲氨基吡啶），分别与 2-溴丙酰氯、2-氯乙酰氯、二氟乙酸酐、三氟乙酸酐、甲基丙烯酰氯、2-丁烯酰氯发生酯化反应，经过柱层析分离纯化，合成卤素原子修饰的性信息素类似物 K1—K4 和碳链末端双键修饰的类似物 K5—K6。采用梯度稀释配制不同浓度(0.001、0.01、0.1、1、10、100 μg·μL^-1)的类似物 K1—K6 溶液，利用不同浓度类似物直接刺激宽胫夜蛾雄蛾触角，测定类似物 K1—K6 的触角电生理（EAG）响应值；在性信息素诱芯中添加不同剂量的类似物配制性信息素类似物诱芯，于 2021 年夏季在北京延庆地区进行田间诱捕试验，根据统计诱芯的雄蛾诱捕量对类似物活性进行分析。【结果】类似物刺激浓度从 0.001 μg·μL^-1增至 100 μg·μL^-1，雄蛾触角对类似物 K1—K5 的 EAG 响应值呈现出逐渐增大的趋势。其中宽胫夜蛾雄蛾触角对化合物顺-11-十六碳烯-2-溴丙酸酯（K1）的响应最强烈，在 100μg·μL^-1下 EAG 响应值为 1.34 mV。而类似物 K5、K6 的 EAG 活性相对较低，其 EAG 响应值在 100 μg·μL^-1下分别为 0.67、0.57mV。田间诱捕试验表明合成的 6 种类似物均表现出较好的生物活性。其中类似物 K5 添加剂量为 100 μg 时，15 d 平均诱捕量最高，为 35.00 头，显著高于性信息素对照。类似物 K1 添加剂量为 10 μg 时，15 d 平均诱捕量为 32.33 头，显著高于性信息素对照。【结论】经过 EAG 测定和田间试验验证，类似物 K1 和 K5 表现出显著的增效活性，可作为宽胫夜蛾性信息素的增效剂；添加不同剂量的类似物 K2、K3、K4、K6 表现出了与性信息素相当的活性。研究结果可为宽胫夜蛾的绿色防控提供科学依据。更多还原

【Abstract】 【Background】In recent years, with the significant increase in the area planted with the newly introduced crop quinoa,Protoschinia scutosa, which prefers quinoa, has gradually increased and become a major pest of quinoa, posing a potential threat to the production of agriculture in China.【Objective】The objective of this study is to synthesize two different types of analogues modified with the polar group of the sex pheromone （Z）-hexadec-11-en-1-yl acetate （Z11-16:Ac）, as the parent structure, and determine the biological activity, providing a theoretical basis for using sex pheromones and analogues for the green control of P.scutosa. 【 Method 】 The sex pheromone precursor （Z）-hexadec-11-en-1-ol （Z11-16:OH） was used as the raw material, and triethylamine was used as the acid-binding agent （4-dimethylaminopyridine was added as the catalyst for the reaction with the anhydride）, and the esterification reactions with 2-bromopropionyl chloride, 2-chloroacetyl chloride, difluoroacetic anhydride,trifluoroacetic anhydride, methacryloyl chloride, and 2-butenoyl chloride were carried out respectively, the halogen atom modified analogues （K1-K4） and carbon chain end double bond modified analogues （K5-K6） were synthesized, separated and purified by column chromatography. Different concentrations (0.001, 0.01, 0.1, 1, 10, 100 μg·μL^-1) of sex pheromone analogues （K1-K6） were prepared by gradient dilution. The EAG response values of analogues K1-K6 were measured by direct stimulation on the male tentacles of P. scutosa using different concentrations of analogues. Sex pheromone analogue trap lures were prepared by adding different doses of analogues to the sex pheromone. The field trapping trials were conducted in the summer of 2021 in Yanqing,Beijing, and the analogue activity was analyzed by counting the male moth in the traps.【Result】As the stimulation concentration increased from 0.001 to 100 μg·μL^-1, the electrophysiological response values of male tentacles to analogues K1 to K5 showed a gradual increase trend. Male tentacles responded most strongly to the compound （Z）-hexadec-11-en-1-yl 2-bromopropanoate （K1）,with a response value of 1.34 mV at 100 μg·μL^-1. The EAG activities of analogues K5 and K6 were relatively poor, with EAG response values of 0.67 and 0.57 mV at 100 μg·μL^-1, respectively. All the six analogues synthesized showed good biological activity in field trapping experiments. K5 had the highest average trapped number of 35.00 heads at an additive level of 100 μg, which was significantly higher than the sex pheromone control. The average number of trapped adults of analogue K1 was 32.33 heads at an additive level of 10 μg during the whole period （15 d） of field trapping tests, which was significantly higher than the sex pheromone control.【Conclusion】The analogues K1 and K5 showed potentiation activity and can be used as potentiators of sex pheromones as verified by EAG and field trials. The addition of different doses of analogues K2, K3, K4 and K6 exhibited comparable activity to sex pheromones. This study provides a scientific and theoretical basis for the green control of P. scutosa.更多还原