马来海松酸长链烷基酰(亚)胺钠的合成及其对小地老虎的拒食活性研究

doi:10.3969/j.issn.0253-2417.2018.05.004

Abstract

Abstract: With maleopimaric acid, dodecylamine, tetradecylamine,hexadecylamineand octadecylamine as the main raw materials, disodium maleopimaric acid amide(C_n-MPA-2Na, n=12, 14, 16, 18) were synthesized through amidation reaction and acid-base neutralization, and their structures were characterized by IR and ¹H NMR. The antifeedant activities of C_n-MPA-2Na (n=12, 14, 16, 18)and sodium maleopimaric acid long chainalkylene amines (C_n-MPA-Na, n=12, 14, 16) reported in reference against Agrotis ypsilon were investigated using the method of leaf disc. The results showed that both C_n-MPA-2Na (n=12, 14, 16, 18) and C_n-MPA-Na (n=12, 14, 16) show good water solubility at room temperature, and the solubility of C_n-MPA-2Na was above 300 g/L. Both the length of alkane and the number of sodium carboxylate in soluble sodium maleopimaric acid long chain alkyl (alkylene) amines showed little influences on its antifeedant activities against A. ypsilion. And C₁₂-MPA-2Na, C₁₈-MPA-2Na and C₁₄-MPA-Na showed strong antifeedant activities against A. ypsilon. The 50% antifeedant concentrations(AFC₅₀) for C₁₂-MPA-2Na, C₁₈-MPA-2Na and C₁₄-MPA-Na were 0.51, 0.54 and 0.77 g/L, respectively.

Key words: maleopimaric acid, synthesis, Agrotis ypsilon, water solubility, antifeedant activities

CLC Number:

TQ35

ZHAI Zhaolan, YAN Xinyan, XU Ji, SONG Zhanqian, SHANG Shibin, RAO Xiaoping. Synthesis of Sodium Maleopimaric Acid Long Chain Alkyl (Alkylene) Amines and Their Antifeedant Activity Against Agrotis ypsilon[J]. Chemistry and Industry of Forest Products, 2018, 38(5): 23-29.

References

[1] 向玉勇,杨茂发. 小地老虎在我国的发生危害及防治技术研究[J]. 安徽农业科学,2008,36(33):14636-14639. XIANG Y Y,YANG M F. Study on the occurrence,damage and control techniques of black cutworm in China[J]. Journal of Anhui Agricultural Sciences,2008,36(33):14636-14639.
[2] 朱玉坤. 昆虫拒食剂研究进展[J]. 世界农药,2012,34(3):28-30. ZHU Y K. A review on advance in insect antifeedants[J]. World Pesticides,2012,34(3):28-30.
[3] 韩招久,肖旭,姜志宽,等. 植物源昆虫拒食剂研究进展[J]. 中华卫生杀虫药械,2014(6):511-515. HAN Z J,XIAO X,JIANG Z K,et al. A brief review of botanical insect antifeedant[J]. Chinese Journal of Hygienic Insecticides & Equipments,2014(6):511-515.
[4] 吕纪增,杨雪巧. 植物源昆虫拒食剂研究与应用前景[J]. 农药市场信息,2005(18):17-18. LU J Z,YANG X Q. The source of insect-repellent insects and their application prospects[J]. Pesticide Market News,2005(18):17-18.
[5] 张文,娄红祥. 天然昆虫拒食剂研究概述[J]. 现代药物与临床,2002,17(1):50-56. ZHANG W,LOU H X. A review of natural insect antifeedants[J]. Drugs & Linic,2002,17(1):50-56.
[6] 韩招久,王宗德,姜志宽,等. 萜类化合物对小菜蛾幼虫的拒食活性[J]. 应用昆虫学报,2007,44(6):863-867. HAN Z J,WANG Z D,JIANG Z K,et al. Antifeedant activity of terpene compounds against larvae of the diamondback moth,Plutella xylostella [J]. Chinese Bulletin of Entomology,2007,44(6):863-867.
[7] 单绍军,哈成勇. 萜类化合物为手性源合成拒食剂研究进展[J]. 化学通报,2004,67(7):492-498. SHAN S J,HA C Y. Progress in synthesis of antifeedants from terpenoids[J]. Chemistry Bulletin,2004,67(7):492-498.
[8] HUANG S Z,MA Q Y,KONG F D,et al. Daphnauranins A and B,two new antifeedantsisolated from Daphne aurantiaca roots[J]. Fitoterapia,2017,122:11-15.
[9] BERNARDES R C,TOMÉ H V V,BARBOSA W F,et al. Azadirachtin-induced antifeeding in Neotropical stingless bees[J]. Apidologie,2017,48(3):275-285.
[10] 宋冰蕾,余小娜,陈燕,等. 含酰胺基团松香基双子表面活性剂的合成与性能[J]. 林产化学与工业,2015,35(6):39-46. SONG B L,YU X N,CHEN Y,et al. Synthesis and properties of rosin-based gemini surfactants with amide group[J]. Chemistry and Industry of Forest Products,2015,35(6):39-46.
[11] ZHANG H B,HUANG X,JIANG J X,et al. Hydrogels with high mechanical strength cross-linked by a rosin-based crosslinking agent[J]. RSC Advances,2017,7(67):42541-42548.
[12] YAN X Y,ZHAI Z L,SONG Z Q,et al. Synthesis and properties of polyester-based polymeric surfactants from diterpenicrosin[J]. Industrial Crops & Products,2017,108:371-378.
[13] WELLSOW J,GRAYER R,VEITCH N,et al. Insect-antifeedant and antibacterial activity of diterpenoids from species of Plectranthus[J]. Phytochemistry,2006,67(16):1818-1825.
[14] LUO S H,HUA J,LI C H,et al. New antifeedant C-20 terpenoids from Leucosceptrum canum[J]. Organic Letters,2012,14(22):5768-5771.
[15] SREELATHA T,HYMAVATHI A,BABU K S,et al. Synthesis and insect antifeedantactivity of plumbagin derivatives with the amino acid moiety[J]. Journal of Agricultural and Food Chemistry,2009,57(14):6090-6094.
[16] ULRICHS C,MEWIS I,ADHIKARY S,et al. Antifeedant activity and toxicity of leaf extracts from Porteresia coarctata Takeoka and their effects on the physiology of Spodoptera litura (F.)[J]. Journal of Pest Science,2008,81(2):79-84.
[17] RAO X P,SONG Z Q,HAN Z J,et al. Synthesis and insect attractant activity of fluorine-containing Pinus diterpenic amides and imines[J]. Natural Product Research,2009,23(9):851-860.
[18] 刘莉,高艳清,饶小平,等. 脱氢枞基酰胺及亚胺衍生物对粘虫的拒食活性[J]. 生物质化学工程,2014,48(6):6-10. LIU L,GAO Y Q,RAO X P,et al. Antifeedant activities of dehydroabietyl amides and imines derivatives against Mythimna separate[J]. Biomass Chemical Engineering,2014,48(6):6-10.
[19] KLEJDYSZ T,ŁEGOSZ B,CZURYSZKIEWICZ D,et al. Biobasedionic liquids with abietateanion[J]. ACS Sustainable Chemistry & Engineering,2016,4(12):6543-6550.
[20] CHOI S J,YIM T,CHO W,et al. Rosin-embedded poly(acrylic acid) binder for silicon/graphite negative electrode[J]. ACS Sustainable Chemistry & Engineering,2016,4(12):6362-6370.
[21] ZHAI Z L,YAN X Y,SONG Z Q,et al. Annular and threadlike wormlike micelles formed by a bio-based surfactant containing an extremely large hydrophobic group[J]. Soft Matter,2018,14:499-507.
[22] 陈立,徐汉虹. 农药复配最佳增效配方筛选方法的探讨[J]. 植物保护学报,2000,27(4):349-354. CHEN L,XU H H. Study on the screening method for optimal synergetis ratio of combined pesticides[J]. Journal of Plant Protection,2000,27(4):349-354.
[23] 吕敏. 梣酮的杀虫活性及作用机理的初步研究[D]. 杨凌:西北农林科技大学博士学位论文,2009. LÜ M. Preliminary studies on the insecticidal activity and action mechanism of fraxinellone[D]. Yangling:Doctoral Dissertation of Northwest Agriculture and Forestry University,2009.
[24] 张琳. 环保型大豆种衣剂的研制及增产机理研究[D]. 武汉:武汉理工大学硕士学位论文,2009. ZHANG L. Study of preparation and yield-increasing mechanism of an environment friendly soybean seed-loatingagent[D]. Wuhan:Master Degree Thesis of Wuhan University of Technology,2009.
[25] JEYASANKAR A. Antifeedant,insecticidal and growth inhibitory activities of selected plant oils on black cutworm,Agrotis ipsilon (Hufnagel) (Lepidoptera:Noctuidae)[J]. Asian Pacific Journal of Tropical Disease,2012,2(Supplement 1):S347-S351.

Synthesis of Sodium Maleopimaric Acid Long Chain Alkyl (Alkylene) Amines and Their Antifeedant Activity Against Agrotis ypsilon

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