摘要
利用阿维菌素具有的2个活性羟基,连续与丙烯酰氯、四乙烯五胺和琥珀酸酐反应,制备了带有酯键并对药物亲和的乳化剂前体;并采用多种技术表征了其结构.该乳化剂前体经中和后,可以与阿维菌素在水中自发形成稳定的纳米农药乳液,纳米乳液的粒径可以通过改变乳液载药量或乳化剂中和程度来调节.该纳米乳液显示出一系列优良性能,包括高载药量、高稳定性、耐光解、低表面张力和高的叶面亲和性.在酯酶存在或强碱性条件下,乳化剂的酯键发生水解,致使乳化剂亲水部分与亲油部分分离,从而促进阿维菌素从颗粒中的释放,故该纳米农药具有比市售阿维菌素乳油更好的杀虫效果.
Based on the two active hydroxyl groups,avermectin reacted with acryloyl chloride,tetraethylenepentamine and succinic anhydride consecutively to obtain a new kind of emulsifier precursor with ester bonds and drug affinity. The structure of the emulsifier precursor was characterized by various techniques. After neutralization,the emulsifier and avermectin could form a stable nanoemulsion in water spontaneously. The particle size of the nanoemulsion could be adjusted by drug loading and neutralization extent. The nanoemulsion exhibited a series of good properties,including high drug loading,high stability,photolysis resistance,low surface tension and high leaf affinity. The ester bonds in the emulsifier could be hydrolyzed in presence of esterase or under strong alkaline,so that the hydrophilic part of the emulsifier could be separated from the lipophilic part,promoting the releasing of avermectin from the particles. Therefore,this nano pesticide exhibited a better insecticidal effect than the commercial avermectin emulsifiable concentrate(EC).
引文
[1] Leonard G. C.,Pest Manag. Sci.,2000,56,51—676
[2] Rosenheim J. A.,Parsa S.,Forbes A. A.,Krimmel W. A.,Law Y. H.,Segoli M.,Sivakoff F. S.,Zaviezo T.,Gross K.,J. Econ. Entomol.,2011,104(2),331—342
[3] Ghormade V.,Deshpande M. V.,Biotechnol. Adv.,2011,29,792—803
[4] Kah M.,Beulke S.,Tiede K.,Hofmann T.,Crit. Rev. Environ. Sci. Technol.,2013,43,1823—1867
[5] Khodakovskaya M.,Dervishi E.,Xu Y.,Li Z. R.,Watanabe F.,Biris A. S.,ACS Nano,2009,3,3221—3227
[6] Melanie K.,Thilo H.,Environ. Inter.,2014,63,224—235
[7] Norman S.,Hongda C.,Ind. Biotechnol.,2012,8(6),340—343
[8] Yu M. L.,Yao J. W.,Liang J.,Zeng Z. H.,Cui B.,Zhao X.,Sun C. J.,Wang Y.,Liu G. Q.,Cui H. X.,RSC Adv.,2017,7,11271—11280
[9] Debnath N.,Das S.,Seth D.,Chandra R.,Bhattacharya S.,Goswami A.,J. Pestic. Sci.,2010,84,99—105
[10] Zhang W. X.,Mei H.,Guan W. X.,Tang L. M.,Chem. J. Chinese Universities,2015,36(6),1208—1212(章文翔,梅豪,关文勋,唐黎明.高等学校化学学报,2015,36(6),1208—1212)
[11] Gogos A.,Knauer K.,Bucheli T.,J. Agric. Food Chem.,2012,60,9781—9792
[12] Anamika R.,Sunil K. S.,Jaya B.,Anil K. B.,Cent. Eur. J. Chem.,2014,12(4),453—469
[13] Sanghamitra A.,Manoranjan B.,Tirthartha C.,RSC Adv.,2015,5,86—90
[14] Xiang Y.,Zhang G.,Chi Y.,Cai D. Q.,Wu Z. Y.,Chem. Eng. J.,2017,328,320—330
[15] Guan W. X.,Zhang W. X.,Tang L. M.,Wang Y.,Cui H. X.,J. Agric. Food Chem.,2018,66(26),6569—6577
[16] Guan W. X.,Tang L. M.,Wang Y.,Cui H. X.,J. Agric. Food Chem.,2018,66(29),7568—7576
[17] Song S. M.,Li M. L.,Gong X. J.,Han H.,Zhou Y. H.,Wang L.,Shuang S. M.,Dong C.,Chem. Res. Chinese Universities,2018,34(2),203—211
[18] Shen B.,Cell,2015,163(6),1297—1300
[19] Yuan H. Z.,Qi S. H.,Yang D. B.,Chin. J. Pestic. Sci.,2000,2(4),66—71(袁会珠,齐淑华,杨代斌.农药学学报,2000,2(4),66—71)
[20] Ren G.,Liu D.,Guo W.,Wang M.,Wu C. N.,Guo M. R.,Ai X. Y.,Wang Y. J.,He Z. G.,Drug. Deliv.,2016,23,1272—1281
[21] Gong Y. J.,Wang Z. H.,Shi B. C.,Kang Z. J.,Zhu L.,Guo X. J.,Liu J. H.,Wei S. J.,Scientia. Agric. Sinica,2011,44(21),4385—4394(宫亚军,王泽华,石宝才,康总江,朱亮,郭晓军,刘建华,魏书军.中国农业科学,2011,44(21),4385—4394)
[22] Wang D. Q.,J. China Agr. Uni.,1994,20(4),431—437(王道全.中国农业大学学报,1994,20(4),431—437)
[23] Burkhard R.,Binz H.,Roux C. A.,Brunner M.,Ruesch O.,Wyss P.,Environ. Toxicol. Chem.,2015,34(2),297—302
[24] Islam M. T.,Sarwar A. K. M. G.,Begum H. H.,Bangladesh J. Plant Taxonomy,2009,16(2),177—180
[25] Rowan S. J.,Cantrill S. J.,Cousins G. R. L.,Sanders J. K. M.,Stoddart J. F.,Angew. Chem. Int. Ed.,2002,41(6),898—952
[26] Newcomb R. D.,Campbell P. M.,Ollis D. L.,Cheah E.,Russell R. J.,Oakeshott J. G.,Proc. Natl. Acad. Sci. USA,1997,94(14),7464—7468
[27] Van F. K.,J. Invertebr. Pathol.,2009,101(1),1—16