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 |
[1] |
LAW J H, REGNIER F E.Pheromones[J].Annual review of biochemistry, 1971, 40 (1) :533-548.
|
[2] |
MLLER 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, LSCHER 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] |
LSTEDT 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, LFSTEDT 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, STVER 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.
|