Scientia Agricultura Sinica ›› 2021, Vol. 54 ›› Issue (3): 556-572.doi: 10.3864/j.issn.0578-1752.2021.03.010


Chemical Synthesis View on Sex Pheromones of Potato Tuberworm (Phthorimaea operculella)

CHEN Yang1(),ZHAO HongYi1,YAN JunJie2,HUANG Jian1(),GAO YuLin2,3()   

  1. 1State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering/Key Laboratory of Green Pesticide and Agriculture Bioengineering, Ministry of Education/Center for Research and Development of Fine Chemicals, Guizhou University, Guiyang 550025
    2State Key Laboratory for Biology of Plant Diseases and Insect Pests, Institute of Plant Protection, Chinese Academy of Agricultural Sciences, Beijing 100193
    3National Center of Excellence for Tuber and Root Crop Research, Chinese Academy of Agricultural Sciences, Beijing 100081
  • Received:2020-06-28 Accepted:2020-07-28 Online:2021-02-01 Published:2021-02-01
  • Contact: Jian HUANG,YuLin GAO;;


Potato is one of the four staple crops in China together with wheat, rice and maize. It plays a key role in ensuring the national food security strategy, reasonably adjusting the agricultural planting structure, and implementing the poverty alleviation strategy. With the continuous expansion of potato planting area, the occurrence of diseases and insect pests in production and storage is becoming more and more serious. Potato tuberworm (Phthorimaea operculella) is a major potato pest, which originated in America and quickly spread to all over the world. Prevention and control strategy of P. operculella mainly include agricultural, chemical and biological methods. With the increasing consciousness of environmental protection, the use of sustainable and ecological green prevention methods of P. operculella sex pheromone has attracted considerable attention of agricultural scientists, biologists and chemists, which provides the possibility to reduce the excessive use and dependence of chemical pesticides. The sex pheromones of P. operculella mainly contain two chemical structures: 4E, 7Z-tridecadiene-1-ol acetate (PTM1) and 4E, 7Z, 10Z-tridecatriene-1-ol acetate (PTM2). The discovery and structure determination process of these two sex pheromones is very tortuous. The chemical synthesis method of these two sex pheromones started in the 1970s, developed in the 1980s and 1990s, and only a few strategies were reported in the 21st century. This process witnessed the rapid development of modern organic synthetic chemistry. How to construct E and Z olefin accurately and efficiently is a challenge for synthesis of PTM1 and PTM2. The key steps of PTM1 synthetic strategy mainly include alkyne reduction or rearrangement reaction, conjugation ring opening, organosilicon induced Beckmann reaction, cross coupling reaction and so on. Up to now, only two cases were reported about the synthesis of PTM2. Due to the addition of a Z-type olefin bond in the structure, the two synthesis routes of PTM2 adopt coupling reaction to introduce diyne block, and then 7Z, 10Z-olefin was synthesis by catalytic hydrogenation reduction of diynes by Raney-Ni or Lindlar-Pd. However, most of the synthetic routes are lengthy, low selectivity of E/Z configuration, and complicated procedure. Developing a facile and efficient synthetic method of sex pheromone of P. operculella will provide the necessary material source for the wide application of green integrated prevention and control technology of P. operculella in the field. It will play a positive role in insect sex pheromone trapping technology as an important means of pest prevention and control.

Key words: potato tuberworm (Phthorimaea operculella), sex pheromone, natural product, biological control, chemical synthesis

Fig. 1

Statistics of the number of research papers on insect sex pheromone from Web of science"

Fig. 2

Chemical structure of sex pheromone of P. operculella"

Fig. 3

Synthesis of sex pheromone analogues of P. operculella by FOUDA et al.[40]"

Fig. 4

The first total synthesis of PTM1 of P. operculella by ROELOFS et al.[42]"

Fig. 5

Synthesis of PTM1 by VOERMAN et al.[67]"

Fig. 6

Synthesis of PTM1 by YADAV et al.[68]"

Fig. 7

Synthesis of PTM1 via Claisen rearrangement by NONOSHITA et al.[69]"

Fig. 8

Synthesis of PTM1 by VASIL’EV et al.[70]"

Fig. 9

Synthesis of PTM1 by ODINOKOV et al.[71]"

Fig. 10

Synthesis of PTM1 by VAKHIDOV et al.[72]"

Fig. 11

Synthesis of PTM1 by ALEXAKIS et al.[73]"

Fig. 12

Synthesis of PTM1 by NISHIYAMA et al.[74]"

Fig. 13

Synthesis of PTM1 by HUTZINGER et al.[75]"

Fig. 14

Synthesis of PTM2 by VOERMAN et al.[67]"

Fig. 15

The first synthesis of PTM2 by FUKAMI et al.[76]"

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