马铃薯块茎蛾性信息素化学合成研究现状

doi:10.3864/j.issn.0578-1752.2021.03.010

Abstract

Abstract:

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

CHEN Yang,ZHAO HongYi,YAN JunJie,HUANG Jian,GAO YuLin. Chemical Synthesis View on Sex Pheromones of Potato Tuberworm (Phthorimaea operculella)[J].Scientia Agricultura Sinica, 2021, 54(3): 556-572.

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References 79

[1]	中国科学技术协会. 2016-2017植物保护学学科发展报告. 北京: 中国科学技术出版社, 2017: 5-20.
	China Association of Science and Technology. 2016-2017 Report on Advances in Plant Protection. Beijing: China Science and Technology Press, 2017: 5-20. (in Chinese)
[2]	郑丽霞, 吴兰花, 余玲, 吴伟坚, 魏洪义. 昆虫类信息素研究进展及应用前景. 植物保护学报, 2018,45(6):1185-1193.
	ZHENG L X, WU L H, YU L, WU W J, WEI H Y. Advances in the research and application prospects of insect parapheromones. Journal of Plant Protection, 2018,45(6):1185-1193. (in Chinese)
[3]	王安佳, 张开心, 梅向东, 高玉林, 张涛, 折冬梅, 宁君. 昆虫性信息素及其类似物干扰昆虫行为的机理和应用研究进展. 农药学学报, 2018,20(4):425-438.
	WANG A J, ZHANG K X, MEI X D, GAO Y L, ZHANG T, SHE D M, NING J. Research progress on mechanisms and applications of insect mating behavior disruption by insect sex pheromones and analogues. Chinese Journal of Pesticide Science, 2018,20(4):425-438. (in Chinese)
[4]	BUTENANDT A, BECKMANN R, STAMM D, HECKER E. Über den sexual lockstoff des seidenspinners Bombyx mori. Reindarstellung und Konstitution. Zeitschrift fur Naturforschung, 1959,14:283-284.
[5]	WITZGALL P, KIRSCH P, CORK A. Sex pheromones and their impact on pest management. Journal of Chemical Ecology, 2010,36:80-100. doi: 10.1007/s10886-009-9737-y pmid: 20108027
[6]	SHEN S, CAO S, ZHANG Z, KONG X, LIU F, WANG G, ZHANG S. Evolution of sex pheromone receptors in Dendrolimus punctatus Walker (Lepidoptera: Lasiocampidae) is divergent from other moth species. Insect Biochemistry and Molecular Biology, 2020,122:103375.
[7]	REGNIER F E, LAW J H. Insect pheromones. Journal of Lipid Research, 1968,9:541-551.
[8]	WRIGHT R H. After pesticides—what? Nature, 1964,204(4954):121-125.
[9]	袁文静. 昆虫性信息素诱捕技术在蔬菜病虫害防治中的示范试验. 现代园艺, 2019(9):36-37, 178.
	YUAN W J. The demonstration experiment of insect sex pheromone trapping technology in vegetable pest control. Modern Horticulture, 2019(9):36-37, 178. (in Chinese)
[10]	刘洪辰, 李桂彬. 昆虫性信息素在生物防治中应用的专利分析. 安徽农业科学, 2018,46(18):191-193.
	LIU H C, LI G B. Analysis of pantent application on insect sex pheromones for biological prevention. Journal of Anhui Agricultural Sciences, 2018,46(18):191-193. (in Chinese)
[11]	中国农药信息网. 昆虫性信息素登记药剂现状, 2020. http://www.chinapesticide.org.cn/hysj/index.jhtml.
	China Pesticide Information Network. Current situation of registered pesticides for insect sex pheromone, 2020. http://www.chinapesticide.org.cn/hysj/index.jhtml. (in Chinese)
[12]	高玉林, 徐进, 刘宁, 周倩, 丁新华, 詹家绥, 成新跃, 黄剑, 鲁宇文, 杨宇红. 我国马铃薯病虫害发生现状与防控策略. 植物保护, 2019,45(5):106-111.
	GAO Y L, XU J, LIU N, ZHOU Q, DING X H, ZHAN J S, CHENG X Y, HUANG J, LU Y W, YANG Y H. Current status and management strategies for potato insect pests and diseases in China. Plant Protection, 2019,45(5):106-111. (in Chinese)
[13]	徐进, 朱杰华, 杨艳丽, 汤浩, 吕和平, 樊明寿, 石瑛, 董道峰, 王贵江, 王万兴, 熊兴耀, 高玉林. 中国马铃薯病虫害发生情况与农药使用现状. 中国农业科学, 2019,52(16):2800-2808.
	XU J, ZHU J H, YANG Y L, TANG H, LÜ H P, FAN M S, SHI Y, DONG D F, WANG G J, WANG W X, XIONG X Y, GAO Y L. Status of major diseases and insect pests of potato and pesticide usage in China. Scientia Agricultura Sinica, 2019,52(16):2800-2808. (in Chinese)
[14]	ZHANG G F, MA D Y, WANG Y S, GAO Y H, LIU W X, ZHANG R, FU W J, XIAN X Q, WANG J, KUANG M, WAN F H. First report of the South American tomato leafminer, Tuta absoluta (Meyrick), in China. Journal of Integrative Agriculture, 2020,19(7):1912-1917.
[15]	何小丽, VERONESI E, STEPHEN W, 祝增荣, 高玉林, 周文武. 警惕茄科作物重大害虫马铃薯木虱入侵风险及危害. 应用昆虫学报, 2019,56(6):1422-1429.
	HE X L, VERONESI E, STEPHEN W, ZHU Z R, GAO Y L, ZHOU W W. The risk posed by the potato psyllid Bactericera cockerelli (Hemiptera: Triozidae) an important invasive pest of solanaceous crops. Chinese Journal of Applied Entomology, 2019,56(6):1422-1429. (in Chinese)
[16]	ZHENG Y Q, ZHANG L M, CHEN B, YAN N S, GUI F R, ZAN Q A, DU G Z, HE S Q, LI Z Y, GAO Y L, XIAO G L. Potato/maize intercropping reduces infestation of potato tuber moth, Phthorimaea operculella (Zeller) by the enhancement of natural enemies. Journal of Integrative Agriculture, 2020,19(2):394-405.
[17]	ZHENG Y Q, XIAO G L, ZHOU W W, GAO Y L, LI Z Y, DU G Z, CHEN B. Midgut microbiota diversity of potato tuber moth associated with potato tissue consumed. BMC Microbiology, 2020,20:58.
[18]	YAN J J, SARKAR S C, MENG R X, REITZ S, GAO Y L. Potential of Steinernema carpocapsae (Weiser) as a biological control agent against potato tuber moth, Phthorimaea operculella (Zeller) (Lepidoptera: Gelechiidae). Journal of Integrative Agriculture, 2020,19(2):389-393.
[19]	LI X, ZHANG X G, XIAO C, GAO Y L, DONG W X. Behavioral responses of potato tuber moth (Phthorimaea operculella) to tobacco plant volatiles. Journal of Integrative Agriculture, 2020,19(2):325-332.
[20]	ZHANG X G, LI X, GAO Y L, LIU Y, DONG W X, XIAO C. Oviposition deterrents in larval frass of potato tuberworm moth, Phthorimaea operculella (Lepidoptera: Gelechiidae). Neotropical Entomology, 2019,48:496-502.
[21]	YUAN H G, WU S Y, LEI Z R, RONDON S I, GAO Y L. Sub-lethal effects of Beauveria bassiana (Balsamo) on field populations of the potato tuberworm Phthorimaea operculella Zeller in China. Journal of Integrative Agriculture, 2018,17(4):911-918.
[22]	RONDON S I, GAO Y. The journey of the potato tuberworm around the world//PERVEEN F K. Moths-Pests of Potato, Maize and Sugar Beet. IntechOpen, 2018: 17-52.
[23]	GAO Y L. Potato tuberworm: A threat for China potatoes. Entomology, Ornithology and Herpetology: Current Research, 2018,7(2):1000e132.
[24]	GAO Y L. Potato tuberworm: Impact and methods for control—Mini review. CAB Reviews, 2018,13(22):1-3.
[25]	CHENG X Y, GAO Y Y, YANG C L, ZHANG X, QIN F F, LU J, GAO Y L, XU R M. Potential of entomopathogenic fungus Isaria javanica for controlling the potato tuberworm Phthorimaea operculella (Zeller) (Lepidoptera: Gelechiidae). Israle Journal of Entomology, 2018,48(2):197-208.
[26]	YUAN H G, LEI Z R, RONDON S I, GAO Y L. Potential of a strain of Beauveria bassiana (Hypocreales: Cordycipitaceae) for the control of the potato tuberworm, Phthorimaea operculella (Zeller). International Journal of Pest Management, 2017,63(4):352-354.
[27]	闫俊杰, 张梦迪, 高玉林. 马铃薯块茎蛾生物学、生态学与综合治理. 昆虫学报, 2019,62(12):1469-1482.
	YAN J J, ZHANG M D, GAO Y L. Biology, ecology and integrated management of the potato tuber moth, Phthorimaea operculella (Lepidoptera: Gelechiidae). Acta Entomologica Sinica, 2019,62(12):1469-1482. (in Chinese)
[28]	韩扬眉, 刘如楠. 技术做媒马铃薯块茎蛾难逃“美人关”. 粮食科技与经济, 2019,44(8):14-15.
	HAN Y M, LIU R N. Technology as a medium: Potato tuber moth cannot escape the “beauty pass”. Grain Science and Technology and Economy, 2019,44(8):14-15. (in Chinese)
[29]	COLL M, GAVISH S, DORI I. Population biology of the potato tuber moth, Phthorimaea operculella (Lepidoptera: Gelechiidae), in two potato cropping systems in Israel. Bulletin of Entomological Research, 2000,90:309-315. pmid: 11020789
[30]	谢春霞. 马铃薯块茎蛾综合防治技术. 中国马铃薯, 2014,28(4):235-237.
	XIE C X. Integrated control techniques of Phthorimaea operculella (Zeller). Chinese Potato Journal, 2014,28(4):235-237. (in Chinese)
[31]	KROSCHEL J, ZEGARRA O. Attract-and-kill as a new strategy for the management of the potato tuber moths Phthorimaea operculella (Zeller) and Symmetrischema tangolias (Gyen) in potato: Evaluation of its efficacy under potato field and storage conditions. Pest Management Science, 2013,69:1205-1215.
[32]	AL-ALI A S, AL-NEAMY I K, ABBAS S A, ABDUL-MASIH A M E. Observations on the biology of the potato tuber moth Phthorimaea// Division of Entomology, Directorate General of Plant Protection, Abu-Ghraib, Iraq. 1975,79:345-351.
[33]	李秀军, 金秀萍, 李正跃. 马铃薯块茎蛾研究现状及进展. 青海师范大学学报(自然科学版), 2005(2):67-70.
	LI X J, JIN X P, LI Z Y. The present status and developing tendency in Phthorimaea operculella research. Journal of Qinghai Normal University (Natural Science Edition), 2005(2):67-70. (in Chinese)
[34]	曹骥. 马铃薯块茎蛾发生规律初探. 植物保护, 1964,2(5):238.
	CAO J. Preliminary study on the occurrence of potato tuber moth. Plant Protection, 1964,2(5):238. (in Chinese)
[35]	中国农药信息网. 马铃薯块茎蛾登记药剂现状. http://www.chinapesticide.org.cn/hysj/index.jhtml.
	China pesticide information network. Status of registration agents for potato tuber moth. http://www.chinapesticide.org.cn/hysj/index.jhtml. (in Chinese)
[36]	LAL L. Relationships between pheromone catches of adult moths, foliar larval populations and plant infestations by potato tuberworm in the field. Tropical Pest Management, 1989,35(2):157-159.
[37]	任彬元, 马中正, 李天娇, 赵中华, 李春广, 王万兴, 闫硕. 西南混作区马铃薯病虫害发生动态及防控工作建议. 中国植保导刊, 2019,39(5):78-83.
	REN B Y, MA Z Z, LI T J, ZHAO Z H, LI C G, WANG W X, YAN S. Occurrence trends of potato diseases and insect pests in southwest mixed cropping area and suggestions for prevention and control. China Plant Protection, 2019,39(5):78-83. (in Chinese)
[38]	ADEESAN C, TAMHANKAR A J, RAHALKAR G W. Sex pheromone gland in the potato tuberworm moth, Phthorimaea operculella. Annals of the Entomological Society of America, 1969,62(3):670-671.
[39]	ONO T, IYATOMI K, SAITO T. Mating behavior of the potato tuber moth, Phthorimaea operculella Zeller. Japanese Journal of Applied Entomology and Zoology, 1972,16(1):51-53.
[40]	FOUDA H G, SEIBER J N, BACON O G. A potent sex attractant for the potato tuberworm moth. Journal of Economic Entomology, 1975,68(4):423-427.
[41]	HINDENLANG D M, MCLAUGHLIN J R, GUILIANO R M, HENDRY L B. A sex pheromone in the potato tuberworm moth, Phthorimaea operculella (Zeller): Biological assay and preliminary chemical investigation. Journal of Chemical Ecology, 1975,1(4):465-473.
[42]	ROELOFS W L, KOCHANSKY J P, CARDE R T, KENNEDY G G, HENRICK C A, LABOVITZ J N, CORBIN V L. Sex pheromone of the potato tuberworm moth, Phthorimaea operculella. Life Sciences, 1975,17(5):699-705. doi: 10.1016/0024-3205(75)90524-x pmid: 1207389
[43]	CARDE R T, KOCHANSKY J P, ROELOFS W L. Sex pheromone for potato tubeworm moth, Phthorimea operculella: US4010255A[P]. (1977-03-01) [2020-06-28].
[44]	YAMAOKA R, FUKAMI H, ISHII S. Isolation and identification of the female sex pheromone of the potato tuberworm moth, Phthorimaea operculella (Zeller). Agricultural and Biological Chemistry, 1976,40(10):1971-1977.
[45]	PERSOONS C J, VOERMAN S, VERWIEL P E J, RITTER F J, NOOYEN W J, MINKS A K. Sex pheromone of the potato tuberworm moth, Phthorimaea operculella: Isolation, identification and field evaluation. Entomologia Experimentalis et Applicata, 1976,20:289-300.
[46]	VOERMAN S, MINKS A K, PERSOONS C J. Elucidation of the sex pheromone system of the potato tuberworm moth, Phthorimaea operculella (Zeller) (Lepidoptera, Gelechiidae): A short review. Potato Research, 1977,20:123-126.
[47]	BACON O G, SEIBER J N, KENNEDY G G. Evaluation of survey trapping techniques for potato tuberworm moths with chemical baited traps. Journal of Economic Entomology, 1976,69(5):569-572.
[48]	RITTER F J, PERSOONS C J. Recent development in insect pheromone research, in particular in the Netherlands. Netherlands Journal of Zoology, 1975,25(3):261-275.
[49]	EL-GARHY M S. Preliminary results with sex pheromones to trap potato tuber worm moths in Saudi Arabia. Potato Research, 1980,23:361-363.
[50]	RAMAN K V. Field trials with the sex pheromone of the potato tuberworm. Environmental Entomology, 1982,11(2):367-370.
[51]	RAMAN K V. Control of potato tuber moth Phthorimaea operculella with sex pheromones in Peru. Agriculture, Ecosystems and Environment, 1988,21:85-99.
[52]	RAMAN K V. Evaluation of a synthetic sex pheromone funnel trap for potato tuberworm moths (Lepidoptera: Gelechiidae). Environmental Entomology, 1984,13(1):61-64.
[53]	TOTH M, BELLAS T E, ROTHSCHILD G H L. Role of pheromone components in evoking behavioral responses from male potato tuberworm moth, Phthorimaea operculella (Zeller) (Lepidoptera: Gelechiidae). Journal of Chemical Ecology, 1984,10(2):271-280. pmid: 24318496
[54]	ORTU S, FLORIS I. Preliminary study on the control of Phthorimaea operculella (Zeller) (Lepidoptera: Gelechiidae) on potato crops in Sardinia. Difesa Delle Piante, 1989,12(1/2):81-88.
[55]	TEJIMA S, ONO T, SAKUMA M. Antennal mechanosensors mediate sex pheromone-induced upwind orientation in the potato tuberworm moth. Physiological Entomology, 2017,42:113-124.
[56]	TEJIMA S, ONO T, SAKUMA M. Aim-then-shoot anemotaxis involved in the hopping approach of potato tuberworm moth Phthorimaea operculella toward a sex pheromone source. Physiological Entomology, 2013,38:292-301.
[57]	ONO T, CHOUVALITWONGPORN P, SAITO T. Comparison of the sex pheromone system between Japanese and Thai populations of the potato tuberworm moth, Phthorimaea operculella (Lepidoptera: Gelechiidae). Applied Entomology and Zoology, 1997,32(3):514-517.
[58]	ONO T. Effect of temperature on biosynthesis of sex pheromone components in potato tuberworm moth, Phthorimaea operculella (Lepidoptera:Gelechidae). Journal of Chemical Ecology, 1994,20(10):2733-2741. doi: 10.1007/BF02036204 pmid: 24241844
[59]	ONO T. Effect of rearing temperature on pheromone component ratio in potato tuberworm moth, Phthorimaea operculella (Lepidoptera: Gelechiidae). Journal of Chemical Ecology, 1993,19(1):71-81.
[60]	ONO T, ORITA S. Field trapping of the potato tuber moth, Phthorimaea operculella (Lepidoptera: Gelechiidae), with the sex pheromone. Applied Entomology and Zoology, 1986,21(4):632-634.
[61]	ONO T. Male approach to the female and the role of two pheromone components in the potato tuber moth, Phthorimaea operculella (Lepidoptera: Gelechiidae). Applied Entomology and Zoology, 1985,20(1):34-42.
[62]	KROSCHEL J, ZEGARRA O. Attract-and-kill: A new strategy for the management of the potato tuber moths Phthorimaea operculella (Zeller) and Symmetrischema tangolias (Gyen) in potato: Laboratory experiments towards optimising pheromone and insecticide concentration. Pest Management Science, 2010,66:490-496. doi: 10.1002/ps.1898 pmid: 20063267
[63]	高玉林, 梅向东, 翁爱珍, 袁慧果. 一种马铃薯块茎蛾诱剂组合物及其应用: CN108077256A[P]. (2018-05-29)[2020-06-28].
	GAO Y L, MEI X D, WENG A Z, YUAN H G . Potato tuber moth attractant composition and its application: CN108077256A[P]. (2018-05-29)[2020-06-28]. (in Chinese)
[64]	高玉林, 梅向东, 翁爱珍, 袁慧果. 一种马铃薯块茎蛾性引诱剂及其用途: CN107864958A[P]. (2018-04-03)[2020-06-28].
	GAO Y L, MEI X D, WENG A Z, YUAN H G. Potato tuber moth sex attractant and its application in trapping potato tuber moth: CN107864958A[P]. (2018-04-03)[2020-06-28]. (in Chinese)
[65]	高玉林, 闫俊杰, 梅向东, 翁爱珍, 王留洋, 折冬梅. 一种马铃薯块茎蛾迷向剂及其应用: CN108812665A[P]. (2018-11-16)[2020-06-28].
	GAO Y L, YAN J J, MEI X D, WENG A Z, WANG L Y, SHE D M. Sex pheromone dispenser for disrupting mating behavior of Phthorimaea operculella and application thereof on potato crops: CN108812665A[P]. (2018-11-16)[2020-06-28]. (in Chinese)
[66]	高玉林, 闫俊杰, 梅向东, 王留洋, 宁君. 一种系统优化的马铃薯块茎蛾性引诱剂及其应用: CN110292043A[P]. (2019-10-01)[2020-06-28].
	GAO Y L, YAN J J, MEI X D, WANG L Y, NING J. System optimized potato tuber moth attractant containing cis-10-tridecene-1- ol acetate and its application: CN110292043A[P]. (2019-10-01)[2020-06-28]. (in Chinese)
[67]	VOERMAN S, ROTHSCHILD G H L. Synthesis of the two components of the sex pheromone systems of the potato tuberworm moth, Phthorimaea operculella (Zeller) (Lepidoptera: Gelechiidae) and field experience with them. Journal of Chemical Ecology, 1978,4(5):531-542.
[68]	YADAV J S, REDDY P S. Allylation of Grignard reagents: Its application for the synthesis of (4E,7Z)-4,7-tridecadienyl acetate, a sex pheromone of potato tuberworm moth. Synthetic Communications, 1986,16(9):1119-1131.
[69]	NONOSHITA K, BANNO H, MARUOKA K, YAMAMOTO H. Organoaluminum-promoted Claisen rearrangement of allyl vinyl ethers. Journal of the American Chemical Society, 1990,112:316-322.
[70]	VASIL’EV A A, SEREBRYAKOV E P. A simple synthesis of 4E,7Z-tridecadien-1-yl acetate, a component of the sex pheromone of the potato moth Phthorimaea operculella (Lepidoptera: Gelechiidae). Russian Chemical Bulletin, 1996,45(9):2232-2235.
[71]	ODINOKOV V N, VAKHIDOV R R, SHAKHMAEV R N, ZORIN V V. Insect pheromones and their analogs. LV. Synthesis of trideca- 4E,7Z-dien-1-yl acetate-component of the sex pheromone of Phthorimaea opercucella. Chemistry of Natural Compounds, 1997,33(3):350-352.
[72]	VAKHIDOV R R, MUSINA I N. Synthesis of 4E,7Z- tridecadien-1-ylacetate, a component of the Phthorimaea opercucella sex pheromone. Chemistry of Natural Compounds, 2007,43(3):282-284.
[73]	ALEXAKIS A, CAHIEZ G, NORMANT J F. Highly stereoselective synthesis of the insect sex pheromone of Phthorimaea operculella and of propylure. Tetrahedron Letters, 1978(23):2027-2030.
[74]	NISHIYAMA H, SAKUTA K, ITOH K. New stereocontrolled approach to some insect pheromones via silicon-directed Beckmann fragmentation. Tetrahedron Letters, 1984,25(2):223-226.
[75]	HUTZINGER M W, OEHLSCHLAGER A C. Stereoselective synthesis of 1,4-dienes. Application to the preparation of insect pheromones (3Z,6Z)-dodeca-3,6-dien-1-ol and (4E,7Z)-trideca-4, 7-dienyl acetate. Journal of Organic Chemistry, 1995,60(14):4595-4601.
[76]	FUKAMI H, ISHII S, YAMAOKA R. Trideca-4,7,10-trienyl acetate isomers, sex pheromones for Phthorimaea operculella: JP53037612A [P]. (1978-04-06) [2020-06-28].
[77]	CHANDEL R S, VASHISTH S, SONI S, KUMAR R, KUMAR V. The potato tuber moth, Phthorimaea operculella (Zeller), in India: Biology, Ecology, and Control. Potato Research, 2020,63:15-39.
[78]	DUNKELBLUM E, LEVI-ZADA A. Pheromone research and development in Israel 1975-2015. Phytoparasitica, 2017,45:619-637.
[79]	YEW J Y, CHUNG H. Insect pheromones: An overview of function, form, and discovery. Progress in Lipid Research, 2015,59:88-105. doi: 10.1016/j.plipres.2015.06.001 pmid: 26080085

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

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