• 中文核心期刊
  • CSCD来源期刊
  • 中国科技核心期刊
  • CA、CABI、ZR收录期刊

Message Board

Respected readers, authors and reviewers, you can add comments to this page on any questions about the contribution, review,        editing and publication of this journal. We will give you an answer as soon as possible. Thank you for your support!

Name
E-mail
Phone
Title
Content
Verification Code
Volume 29 Issue 7
Jul.  2014
Turn off MathJax
Article Contents
SUN Jian-sheng, WEI Hui, LIN Shuo, GU Xiao-jun. Synthesis and Microencapsulation of Insect Sex Pheromones[J]. Fujian Journal of Agricultural Sciences, 2014, 29(7): 707-714. doi: 10.19303/j.issn.1008-0384.2014.07.021
Citation: SUN Jian-sheng, WEI Hui, LIN Shuo, GU Xiao-jun. Synthesis and Microencapsulation of Insect Sex Pheromones[J]. Fujian Journal of Agricultural Sciences, 2014, 29(7): 707-714. doi: 10.19303/j.issn.1008-0384.2014.07.021

Synthesis and Microencapsulation of Insect Sex Pheromones

doi: 10.19303/j.issn.1008-0384.2014.07.021
  • Received Date: 2014-04-12
  • Publish Date: 2014-07-18
  • Insect sex pheromone plays an important role in the integrated pest management.The available methods of synthesizing sex pheromones include the witting reaction, acetylene route, Grignard reagent coupling method, etc.An important means in controlling drug release, microencapsulation appeared to be potentially applicable in the case of insect sex pheromone as well.This paper reviews various methods of sex pheromone synthesis and microencapsulation.Their advantages, limitations and application prospect are summarized.
  • loading
  • [1]
    LAW J H, REGNIER F E.Pheromones[J].Annual review of biochemistry, 1971, 40 (1) :533-548.
    [2]
    MLLER M, BUCHBAUER G.Essential oil components as pheromones.A review[J].Flavour and Fragrance Journal, 2011, 26 (6) :357-377.
    [3]
    姜勇, 雷朝亮.昆虫聚集信息素[J].昆虫学报, 2002, 45 (6) :822-832.
    [4]
    EVENDEN M L, GRIES R.Plasticity of male response to sex pheromone depends on physiological state in a long-lived moth[J].Animal Behaviour, 2008, 75 (2) :663-672.
    [5]
    孟宪佐.昆虫性信息素的应用[J].生物学通报, 1997, 32 (3) :46-47.
    [6]
    RAFAELI A.Pheromone biosynthesis activating neuropeptide (PBAN) :regulatory role and mode of action[J].General and comparative endocrinology, 2009, 162 (1) :69-78.
    [7]
    MILLAR J G, MIDLAND S L.Synthesis of the sex pheromone of the obscure mealybug, the first example of a new class of monoterpenoids[J].Tetrahedron letters, 2007, 48 (36) :6377-6379.
    [8]
    MORI K.Significance of chirality in pheromone science[J].Bioorganic and medicinal chemistry, 2007, 15 (24) :7505-7523.
    [9]
    范晓军, 李瑜, 李瑶, 等.昆虫性信息素研究进展[J].安徽农业科学, 2010, (9) :4636-4638.
    [10]
    KARLSON P, LSCHER M.‘Pheromones’:a new term for a class of biologically active substances[J].Nature, 1959, 183:55-56.
    [11]
    KARLSON P, BUTENANDT A.Pheromones (ectohormones) in insects[J].Annual review of entomology, 1959, 4 (1) :39-58.
    [12]
    BUTENANDT A, BECKMANN R, STAMM D, et al.Uber den sexual-lockstoff des seidenspinners bombyx morireindarstellung und konstitution[J].Zeitschrift Fur Naturforschung Part B-Chemie Biochemie Biophysik Biologie Und Verwandten Gebiete, 1959, 14 (4) :283-284.
    [13]
    马涛, 温秀军, 李兴文.昆虫性信息素人工合成技术研究进展[J].世界林业研究, 2012, 25 (6) :46-51.
    [14]
    HRDY I, MAREK J, KRAMPL F.Sexual pheromone activity of 8-dodecenyl and 11-tetradecenyl acetates for males of several lepidopteran species in field trials[J].Acta Entomologica Bohemoslovaca, 1979, 76 (2) :65-84.
    [15]
    CHOW Y S, TSAI R S, GRIES G, et al.Preliminary identification of the sex pheromone of Orgyia postica (Walker) (Lepidoptera:Lymantriidae) [J].Entomologia Sinica, 2001, (8) :13-20.
    [16]
    KOUTEK B, STREINZ L, ROMANUK M.Syntheses of Insect Sex Pheromones[J].ChemInform, 1999, 30 (6) :899-954.
    [17]
    朱卫华, 刘万军, 张金桐.昆虫性信息素的研究进展[J].山西林业科技, 2007, (2) :24-27.
    [18]
    杨晓梅, 马莎, 黄飞, 等.小菜蛾性信息素成分的合成[J].化学试剂, 2013, 35 (7) :659-661.
    [19]
    宗广辉, 颜世强, 梁晓梅, 等.小菜蛾性信息素的合成[J].有机化学, 2011, 31 (12) :2126-2130.
    [20]
    周维善, 林国强.昆虫性信息素的结构测定和手性昆虫信息素的合成[J].化学进展, 1990, (3) :27-47.
    [21]
    MITHRAN S, MAMDAPUR V R.A facile synthesis of the Oriental Fruit Moth sex-pheromone[J].Chemistry and Industry, 1986, 20:711-711.
    [22]
    LI J M, YONG J P, HUANG F L, et al.A facile synthesis of the sex pheromone of Grapholitha molesta[J].Chemistry of Natural Compounds, 2012, 48 (1) :103-105.
    [23]
    HASSARAJANI S A, SUBARAMAN A S, MAMDAPUR V R.Facile synthesis of pheromone of Dichocrocis punctiferalis, a serious pest of spices[J].Organic preparations and procedures international, 1994, 26 (5) :571-573.
    [24]
    HORIIKE M, TANOUCHI M, HIRANO C.Synthesis of insect sex pheromones and their homologues.2.A convenient method for synthesizing (Z) -alkenols and their acetates[J].Agricultural and Biological Chemistry, 1980, 44 (2) :257-261.
    [25]
    PICCARDI P, CAPIZZI A, CASSANI G, et al.A sex pheromone component of the Old World Bollworm Heliothis armigera[J].Journal of Insect Physiology, 1977, 23 (11) :1443-1445.
    [26]
    黄文芳, 肖文精, 王今红.Wittig反应的研究——Ⅳ.苹果蠹蛾性信息素E, E-8, 10-十二碳二烯-1-醇立体选择性的合成[J].有机化学, 1986, (5) :376-378.
    [27]
    ABAD J L, FABRIAS G, CAMPS F.Synthesis of deuterated fatty acids to investigate the biosynthetic pathway of disparlure, the sex pheromone of the gypsy moth, Lymantria dispar[J].Lipids, 2004, 39 (4) :397-401.
    [28]
    程时远.昆虫性信息素的固相合成[J].武汉师范学院学报:自然科学版, 1982, (1) :72-80.
    [29]
    刘孟英, 曾孝农, 阎忠诚.桃小食心虫性信息素——顺-7-二十碳烯酮-11和顺-7-十九碳烯酮-11的合成[J].化学学报, 1981, 39 (5) :475-480.
    [30]
    古昆, 张玉顺, 陶云海, 等.马尾松毛虫性信息素的立体选择性合成新法[J].有机化学, 2003, 23 (S1) :343-343.
    [31]
    TAMAKI Y, KAWASAKI K, YAMADA H, et al. (Z) -11-Hexadecenal and (Z) -11-hexadecenyl acetate:Sex-pheromone components of the diamondback moth (Lepidoptera:Plutellidae) [J].Applied Entomology and Zoology (Japan) , 977, (12) :208-210.
    [32]
    陈家威, 蒋济隆, 潘贻军.立体定向合成粘虫性信息素[J].有机化学, 1987, (5) 373-375.
    [33]
    MILLAR J G.Stereospecific synthesis of the sex pheromone of the passionvine mealybug, Planococcus minor[J].Tetrahedron Letters, 2008, 49 (2) :315-317.
    [34]
    张学海, 郭广忠, 林国强, 等.昆虫信息素结构鉴定和合成的研究XXII:白杨透翅蛾的性信息素[J].有机化学, 1985, (2) :183-187.
    [35]
    李正名, SCHWARZ M.一种合成亚洲玉米螟性外激素的新方法[J].中国科学B辑, 1984, (1) :38-43.
    [36]
    王胜新, 么恩云, 李正名.槐尺蠖性信息素的不对称合成[J].化学通报, 1992, (10) :22-25.
    [37]
    陈家威.应用聚合物试剂合成昆虫性信息素[J].化学试剂, 1991, 13 (6) :349-354.
    [38]
    杨小平, 陈小茹.1, 3-二烯型昆虫性信息素的合成[J].湘潭师范学院学报, 1990, 11 (6) :70-76.
    [39]
    MORI K.Simple synthesis of sex pheromones of codling moth and red bollworm moth by the coupling of Grignard reagents with allylic halides[J].Tetrahedron, 1974, 30 (20) :3807-3810.
    [40]
    刘天麟, 刘子平, 李正名.槐尺蠖性信息素的合成[J].农药, 1991, 30 (5) :12-13.
    [41]
    祝钧, 周磊, 张晓娟, 等.光学活性桃潜叶蛾性信息素的合成[J].精细化工, 2009, 26 (9) :867-869.
    [42]
    LSTEDT C, BENGTSSON M.Sex pheromone biosynthesis of (E, E) -8, 10-dodecadienol in codling moth Cydia pomonellainvolves E9desaturation[J].Journal of chemical ecology, 1988, 14 (3) :903-915.
    [43]
    ZHAO C H, ADLOF R O, LFSTEDT C.Sex pheromone biosynthesis in the pine caterpillar moth, Dendrolimus punctatus (Lepidoptera:Lasiocampidae) :pathways leading to Z5-monoene and 5, 7-conjugated diene components[J].Insect biochemistry and molecular biology, 2004, 34 (3) :261-271.
    [44]
    严赞开, 何佶, 张钟宁.美国白蛾性信息素 (9Z, 12Z) -十八碳二烯醛及 (9Z, 12Z, 15Z) -十八碳三烯醛的合成[J].农药学学报, 2002, 4 (2) :85-88.
    [45]
    陈子康, 成莹, 杨慧.棉褐带卷叶蛾性信息素的立体专一性合成[J].北京师范大学学报, 1989, (2) :54-57.
    [46]
    CRITCHLEY B R, CAMPION D G, MCVEIGH L J, et al.Control of pink bollworm, Pectinophora gossypiella (Saunders) (Lepidoptera:Gelechiidae) , in Egypt by mating disruption using hollow-fibre, laminate-flake and microencapsulated formulations of synthetic pheromone[J].Bulletin of entomological research, 1985, 75 (2) :329-346.
    [47]
    许国庆, 蔡忠杰, 刘培斌.甜菜夜蛾性信息素的研究与应用[J].昆虫知识, 2008, 45 (3) :357-361.
    [48]
    TTERHOLT C A, DELWICHE M J, RICE R E, et al.Controlled release of insect sex pheromones from paraffin wax and emulsions[J].Journal of controlled release, 1999, 57 (3) :233-247.
    [49]
    李庆燕, 刘金龙, 赵龙龙, 等.缓释技术在性信息素防治害虫中的应用[J].中国生物防治学报, 2012, 28 (4) :589-593.
    [50]
    陆鹏飞.利用性信息素防治豆野螟的生物学基础及应用技术研究[D].武汉:华中农业大学, 2007.
    [51]
    邓建宇, 杜家纬.小菜蛾性信息素剂型的研究[J].上海交通大学学报:农业科学版, 2004, 21 (B12) :52-55.
    [52]
    KROBER H, TEIPEL U.Microencapsulation of particles using supercritical carbon dioxide[J].Chemical Engineering and Processing:Process Intensification, 2005, 44 (2) :215-219.
    [53]
    PATRA D, SANYAL A, ROTELLO V M.Colloidal microcapsules:self-assembly of nanoparticles at the liquidliquid interface[J].Chemistry, an Asian Journal, 2010, 5 (12) :2442-2453.
    [54]
    乔吉超, 胡小玲, 管萍, 等.药用微胶囊的制备[J].化学进展, 2008, 20 (1) :171-180.
    [55]
    HE P, DAVIS S S, ILLUM L.In vitro evaluation of the mucoadhesive properties of chitosan microspheres[J].International Journal of Pharmaceutics, 1998, 166 (1) :75-88.
    [56]
    郝红, 梁国正.微胶囊技术及其应用[J].现代化工, 2002, 22 (3) :60-67.
    [57]
    谈金辉, 刘文涵, 单胜艳.药物微胶囊技术及其应用[J].天津化工, 2003, 17 (6) :4-7.
    [58]
    孟锐, 李晓刚, 周小毛, 等.药物微胶囊壁材研究进展[J].高分子通报, 2012, (3) :28-37.
    [59]
    许时婴, 张晓鸣, 夏书芹, 等.微胶囊技术-原理与应用[M].北京:化学工业出版社, 2006:31-78.
    [60]
    YIN W, YATES M Z.Effect of interfacial free energy on the formation of polymer microcaps-ules by emulsification freezedrying[J].Langmuir, 2008, 24 (3) :701-708.
    [61]
    SHIM J W, KIM S H, JEON S J, et al.Microcapsules with tailored nanostructures by microphase separation of block copolymers[J].Chemistry of Materials, 2010, 22 (19) :5593-5600.
    [62]
    ADDISON T, CAYRE O J, BIGGS S, et al.Polymeric microcapsules assembled from a cationic/zwitterionic pair of responsive block copolymer micelles[J].Langmuir, 2010, 26 (9) :6281-6286.
    [63]
    FUKUI Y, MARUYAMA T, IWAMATSU Y, et al.Preparation of monodispersed polyelectrolyte microcapsules with high encapsulation efficiency by an electrospray technique[J].Colloids and Surfaces A:Physicochemical and Engineering Aspects, 2010, 370 (1) :28-34.
    [64]
    HWANG Y K, JEONG U, CHO E C.Production of uniformsized polymer core-shell microcapsules by coaxial electrospraying[J].Langmuir, 2008, 24 (6) :2446-2451.
    [65]
    SEOK KWON O, JANG J, BAE J.A review of fabrication methods and applications of novel tailored microcapsules[J].Current Organic Chemistry, 2013, 17 (1) :3-13.
    [66]
    陈增良, 张钟宁.昆虫性信息素微胶囊的研究进展[J].昆虫知识, 2008, 45 (3) :362-367.
    [67]
    徐妍, 吴国林, 吴学民, 等.梨小食心虫性信息素微囊化及释放特性[J].农药学学报, 2009, 11 (1) :65-71.
    [68]
    顾相伶, 朱晓丽, 张志国, 等.复凝聚法制备昆虫激素模拟物十二醇微胶囊及其释放性能[J].高等学校化学学报, 2008, 29 (6) :1247-1254.
    [69]
    GU X L, ZHU X, KONG X Z, et al.Comparisons of simple and complex coacervations for preparation of sprayable insect sex pheromone microcapsules and release control of the encapsulated pheromone molecule[J].Journal of microencapsulation, 2010, 27 (4) :355-364.
    [70]
    韩路路, 毕良武, 赵振东, 等.微胶囊的制备方法研究进展[J].生物质化学工程, 2011, 45 (3) :41-46.
    [71]
    陈增良, 方宇凌, 张钟宁.小菜蛾性信息素微胶囊的合成及其田间诱捕和迷向活性研究[J].科学通报, 2007, 52 (7) :797-802.
    [72]
    SHULKIN A, STVER H D.Polymer microcapsules by interfacial polyaddition between styrene–maleic anhydride copolymers and amines[J].Journal of Membrane Science, 2002, 209 (2) :421-432.
    [73]
    GENTRY C R, BIERL-LEONHARDT B A, BLYTHE J L, et al.Air permeation tests with orfralure for reduction in trap catch of oriental fruit moths[J].Journal of Chemical Ecology, 1980, 6 (1) :185-192.
    [74]
    BEROZA M, STEVENS L J, BIERL B A, et al.Pre-and postseason field tests with disparlure, the sex pheromone of the gypsy moth, to prevent mating[J].Environmental entomology, 1973, 2 (6) :1051-1057.
    [75]
    KLUN J A, CHAPMAN O L, MATTES K C, et al.European Corn Borer and Redbanded Leafroller:disruption of reproduction behavior[J].Environmental Entomology, 1975, 4 (6) :871-876.
    [76]
    MINKS A K, VOERMAN S, KLUN J A.Disruption of pheromone communication with microencapsulated antipheromones against adoxophyes orana[J].Entomologia Experimentalis et Applicata, 1976, 20 (2) :163-169.
    [77]
    CAMPION D G, MCVEIGH L J, MURLIS J, et al.Communication disruption of adult Egyptian cotton leafworm Spodoptera littoralis (Boisd.) (Lepidoptera, Noctuidae) in Crete using synthetic pheromones applied by microencapsulation and dispenser techniques[J].Bulletin of Entomological Research.1976, 66 (02) :335-344.
    [78]
    GENTRY C R, YONCE CE, BIERL-LEONHARDT B A.Oriental fruit moth:mating disruption trials with pheromone[J].Insect suppression with controlled release pheromone systems, 1982, 2:107-116.
    [79]
    SANDERS C J, WEATHERSTON J.Sex pheromone of the eastern spruce budworm (Lepidoptera:Tortricidae) :Optimum blend of trans-and cis-11-tetradecenal[J].The Canadian Entomologist, 1976, 108 (11) :1285-1290.
    [80]
    CAMPION D G, MCVEIGH L J, HUNTER-JONES P, et al.Evaluation of microencapsulated formulations of pheromone components of the Egyptian cotton leafworm in Crete[M].Mitchell E., Ed.Management of Insect Pests with Semiochemicals, Springer US.1981:253-265.
    [81]
    MCLAUGHLIN J R, MITCHELL E R, TUMLINSON J H.Evaluation of some formulations for dispensing insect pheromones in field and orchard crops[C]//Proc Controlled Release Pesticide Symp Wright State Univ, Dayton, Ohio, 1975, 209:8-10.
    [82]
    CARDER T, TRAMMEL K, ROELOFS W L.Disruption of sex attraction of the Redbanded Leafroller (Argyrotaenia velutinana) with Microencapsulated Pheromone Components[J].Environmental Entomology, 1975, 4 (3) :448-450.
    [83]
    TASCHENBERG E F, ROELOFS W L.Pheromone communication disruption of the grape berry moth with microencapsulated and hollow fiber systems[J].Environmental Entomology, 1976, 5 (4) :688-691.
    [84]
    EL-SAYED A M, TRIMBLE R M.Relative attractiveness of natural and synthetic pheromone of three tortricid tree fruit pests[J].Environmental entomology, 2002, 31 (6) :960-964.
    [85]
    CHISHOLM M D, UNDERHILL E W, STECK W F.Field Trapping of the Diamondback Moth (Plutella xylostella) using synthetic sex attractants[J].Environmental Entomology, 1979, (8) :516-518.
    [86]
    KAWASAKI K.Effects of ratio and amount of the two sexpheromonal components of the Diamondback Moth on male behavioral response[J].Applied entomology and zoology, 1984, 19 (4) :436-442.
    [87]
    KOSHIHARA T, YAMADA H.Field attractiveness of the synthetic sex-pheromone of the Diamondback Moth, Plutella xylostella (L.) [J].Applied Entomology and Zoology, 1978, 13 (2) :138-141.
    [88]
    魏辉, 田厚军, 陈艺欣, 等.小菜蛾成虫对性信息素与寄主挥发性物质的触角电位反应[J].福建农林大学学报:自然科学版, 2013, 42 (5) :471-476.
    [89]
    BARTELT R J, VETTER R S, CARLSON D G, et al.Pheromone combination lures for Carpophilus (Coleoptera:Nitidulidae) species[J].Journal of Economic Entomology, 1995, 88 (4) :864-869.
    [90]
    陈丽丽, 李莉, 何元密, 等.小菜蛾性信息素田间配方筛选及气象因素影响探究[J].中国植保导刊, 2010, (S1) :55-57.
    [91]
    KNIGHT A L, LARSEN T E, KETNER K C.Rainfastness of a microencapsulated sex pheromone formulation for Codling Moth (Lepidoptera:Tortricidae) [J].Journal of Economic Entomology, 2004, 97 (6) :1987-1992.
    [92]
    KNIGHT A L, LARSEN T E.Creating point sources for Codling Moth (Lepidoptera:Tortricidae) with low-volume sprays of a microencapsulated sex pheromone formulation[J].Environmental Entomolog, 2008, 37 (5) :1136-1144.
    [93]
    焦晓国, 宣维健, 盛承发.性信息素在害虫测报中的应用研究进展[J].植物保护, 2006, 32 (6) :9-13.
    [94]
    WALDSTEIN D E, GUT L J.Effects of rain and sunlight on oriental fruit moth (Lepidoptera:Tortricidae) pheromone microcapsules applied to apple foliage[J].Journal of Agricultural and Urban Entomology, 2004, 21 (2) :117-128.
    [95]
    WALDSTEIN D E, GUT L J.Comparison of microcapsule density with various apple tissues and formulations of oriental fruit moth (Lepidoptera:Tortricidae) sprayable pheromone[J].Journal of economic entomology, 2003, 96 (1) :58-63.
    [96]
    盛承发, 王红托, 王少丽, 等.月相与棉红铃虫性诱剂蛾峰日关系的探讨[J].中国棉花, 2003, 30 (2) :13-14.
    [97]
    孟宪佐, 汪宜蕙, 叶孟贤.用性信息素诱捕法大面积防治梨小食心虫的田间试验[J].昆虫学报, 1985, 28 (2) :142-147.
    [98]
    KNIGHT A L, LARSON T L, KETNER K, et al.Field evaluations of concentrated spray applications of microencapsulated sex pheromone for codling moth (Lepidoptera:Tortricidae) [J].Environmental entomology, 2008, 37 (4) :980-989.
  • 加载中

Catalog

    通讯作者: 陈斌, bchen63@163.com
    • 1. 

      沈阳化工大学材料科学与工程学院 沈阳 110142

    1. 本站搜索
    2. 百度学术搜索
    3. 万方数据库搜索
    4. CNKI搜索

    Article Metrics

    Article views (139) PDF downloads(5) Cited by()
    Proportional views
    Related

    /

    DownLoad:  Full-Size Img  PowerPoint
    Return
    Return