中国农业科学 ›› 2022, Vol. 55 ›› Issue (23): 4640-4650.doi: 10.3864/j.issn.0578-1752.2022.23.006

• 植物保护 • 上一篇    下一篇

陌夜蛾性信息素类似物的合成及其生物活性

任梓齐1,2(),康玉洁3,李海珍4,王连刚4,马好运1,李慧1,王留洋1,梅向东1,*(),宁君1,*()   

  1. 1中国农业科学院植物保护研究所植物病虫害生物学国家重点实验室,北京 100193
    2东北林业大学生命科学学院/东北盐碱植被恢复与重建教育部重点实验室,哈尔滨 150040
    3平度市农业农村局植保科,山东青岛 266799
    4青岛市农业技术推广中心,山东青岛 266299
  • 收稿日期:2022-07-13 接受日期:2022-08-14 出版日期:2022-12-01 发布日期:2022-12-06
  • 联系方式: 任梓齐,E-mail:445921744@qq.com。
  • 基金资助:
    国家重点研发计划(2021YFD1400200)

Synthesis and Bioactivity of Sex Pheromone Analogues of Trachea atriplicis

REN ZiQi1,2(),KANG YuJie3,LI HaiZhen4,WANG LianGang4,MA HaoYun1,LI Hui1,WANG LiuYang1,MEI XiangDong1,*(),NING Jun1,*()   

  1. 1State Key Laboratory for Biology of Plant Diseases and Insect Pests, Institute of Plant Protection, Chinese Academy of Agricultural Sciences, Beijing 100193
    2College of Life Sciences, Northeast Forestry University/Key Laboratory of Saline-Alkali Vegetation Ecology Restoration, Ministry of Education, Harbin 150040
    3Plant Protection Section, Pingdu Bureau of Agriculture and Rural Affairs, Qingdao 266799, Shandong
    4Qingdao Agricultural Technology Extension Center, Qingdao 266299, Shandong
  • Received:2022-07-13 Accepted:2022-08-14 Published:2022-12-01 Online:2022-12-06

摘要: 背景 陌夜蛾(Trachea atriplicis)作为一种重要食叶害虫,近年来,由于其数量以及危害程度的不断增加,已对我国华北、华东等地区的农林业造成重大危害,尤其是对荞麦等作物的产量构成严重威胁。目的 以陌夜蛾性信息素主要组分顺-11-十六碳烯乙酸酯(Z11-16:Ac)为母体结构,合成6种具有不同生物活性的性信息素类似物,为陌夜蛾的综合治理开辟一种新型环境友好的防治策略。方法 选用性信息素组分的前体顺-11-十六碳烯-1-醇(Z11-16:OH)为原料,在缚酸剂和催化剂的作用下,与酸酐或酰氯发生反应,通过硅胶柱层析进行分离纯化后,合成性信息素类似物共6种。包括极性基团为氨基甲酸酯的性信息素类似物M3、M4,极性基团末端引入不饱和键的性信息素类似物M5、M6,以及卤素原子修饰的性信息素类似物M7、M8。通过触角电生理试验(EAG)测定不同剂量性信息素类似物直接刺激下的EAG响应值,并于北京市延庆区进行田间试验对性信息素类似物的生物活性进行验证。结果 EAG试验表明,类似物M1、M2、M6、M7和M8具有显著的剂量-效应关系。其中陌夜蛾雄蛾触角对类似物M7的响应最为强烈,在100 μg剂量下响应值达2.36 mV,是同剂量条件下Z11-16:Ac响应值的77.9%。而M3—M5在10—1 000 μg剂量下,与性信息素组分Z11-16:Ac的相对响应值之间存在显著差异(P<0.05),M5的EAG响应整体活性表现较差,最高相对响应值仅为性信息素组分的21.2%。田间试验表明,类似物M1和M5在添加剂量为1 μg时,平均诱捕量分别为38.00和35.67头/诱捕器/15 d,与性信息素对照相比存在显著差异;类似物M7在添加剂量为100 μg时,平均诱捕量为29.67头/诱捕器/15 d,显著高于性信息素对照;类似物M4具有潜在的抑制活性,随着其添加剂量的增加,平均诱捕量逐渐减少,当添加剂量为1 000 μg时,平均诱捕量仅有3.33头/诱捕器/15 d。 结论经过EAG试验和田间试验验证,类似物M1、M5和M7具有显著的增效活性,可以用作性信息素的增效剂,类似物M4具有显著的抑制活性,可以用作性信息素的抑制剂。研究结果可为使用性信息素类似物绿色防控陌夜蛾提供理论依据。

关键词: 陌夜蛾, 性信息素类似物, 化学合成, 生物活性, 田间应用

Abstract:

【Background】 Trachea atriplicis is an important leaf-eating pest, which has caused great harm to agriculture and forestry in North China, East China, and other regions in recent years due to its increasing numbers and the level of hazards, especially posing a serious threat to the yield of crops such as buckwheat.【Objective】Based on the maternal structure (Z)-hexadec-11-en-1-yl acetate (Z11-16:Ac), which is the main component of the sex pheromone of T. atriplicis, six sex pheromone analogues with different bioactivities were synthesized. The aim was to open up a novel environment-friendly control strategy for the comprehensive treatment of T. atriplicis.【Method】 As the raw material, the sex pheromone precursor (Z)-hexadec-11-en-1-ol (Z11-16:OH) was used to react with an acid anhydride or acyl chloride under the action of an acid binding agent and catalyst. After being separated and purified by silica gel column chromatography, a total of six synthetic pheromone analogues were obtained, including M3 and M4, the sex pheromone analogues with carbamate polar groups, M5 and M6, the sex pheromone analogues with the unsaturated bond at the end of the polar group, and sex pheromone analogues M7 and M8 with halogen atom modification. The electrophysiological response values under direct stimulation of different doses with sex pheromone analogues were measured by the EAG test, and the biological activities of sex pheromone analogues were verified in field experiments conducted in Yanqing, Beijing in 2021.【Result】 The EAG test showed that analogues M1, M2, M6, M7, and M8 had significant dose-dependent relationships. In particular, T. atriplicis showed the strongest response to analogue M7, with a response value of 2.36 mV at the dose of 100 μg, which was 77.9% of that of the response value of Z11-16:Ac at the same dose. While there were significant differences (P<0.05) between the relative response values of M3-M5 and sex pheromone components Z11-16:Ac at the doses of 10-1 000 μg. The M5 displayed lowest EAG response and the highest relative response value was only 21.2% of the sex pheromone fraction. As shown in the field trials, the average capture amount of analogues M1 and M5 was 38.00 and 35.67 moths/trap/15 d at an addition of 1 μg, respectively, which was significantly different compared with the sex pheromone control. The analogue M7 trapped 29.67 moths/trap/15 d at an addition of 100 μg, which was also significantly higher than that of the sex pheromone control. The analogue M4 showed potential inhibitory activity against sex pheromone, and the average capture amount decreased gradually with the increase of its addition, the average capture amount was only 3.33 moths/trap/15 d at the dose of 1 000 μg.【Conclusion】 The EAG tests and field trials verified that the analogues M1, M5, and M7 showed significant synergistic activity and could be developed as synergists of sex pheromones. The analogue M4 showed significant inhibitory activity, which could be used as an inhibitor of sex pheromones. This study provides a necessary theoretical basis for the use of sex pheromone analogues to control T. atriplicis in a green way.

Key words: Trachea atriplicis, sex pheromone analogue, chemical synthesis, bioactivity, field application