Abstract
The inclusion of atrazine with 2-hydroxypropyl-β-cyclodextrin (HPCD) was synthesized by ultrasonic method, and it was characterized by UV, XRD and 1H NMR. The solubility in water and the bioactivity of the inclusion were also studied here. The results indicated that the UV maximum absorption wavelength of the inclusion remained at 223 nm, while its intensity decreased. The XRD peaks of atrazine disappeared, weakened and shifted in the inclusion, and the chemical shift of H-3 and H-5 of cyclodextrin inner cavity led to the upfield. The characterization data showed that the atrazine-HPCD inclusion had already formed. At the same time, the solubility of the atrazine-HPCD inclusion in water became 20.08 times as that of atrazine. Moreover, the atrazine-HPCD inclusion had better herbicidal activity. When the concentration of the inclusion was 6.5 mg/mL, the inhibition ratios of the inclusion to taproot length, taproot fresh weight, sprout length and sprout fresh weight of barnyard grass were 66.96%, 57.22%, 70% and 57.53%, respectively, which were all higher than those of atrazine.
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References
Coleman J O D, Frova C, Schröder P et al. Exploiting plant metabolism for the phytoremediation of persistent herbicides[J]. Environmental Science and Pollution Research, 2002, 9(1): 18–28.
Sun Ke. Market and outlook of the top ten herbicides in the world[J]. Agrochemicals, 2013, 52(5): 317–322 (in Chinese).
Yi Yang. The herbicide atrazine falls into disabled storm after paraquat and acetochlor[J]. Pesticide Market News, 2012(6): 21–22 (in Chinese).
Zhang Jinyan, Wang Yanfeng, Wang Zhijun. The present situation and development proposal of pesticide agent production industry in our country[J]. Heilongjiang Agricultural Science, 2001(2): 39–41 (in Chinese).
Meng X H, Pan Q Y, Liu Y. Preparation and properties of phytosterols with hydroxypropyl β-cyclodextrin inclusion complexes[J]. European Food Research and Technology, 2012, 235(6): 1039–1047.
Bonini M, Rossi S, Karlsson G. Self-assembly of betacyclodextrin in water (Part 1): Cryo-TEM and dynamic and static light scattering[J]. Langmuir, 2006, 22(4): 1478–1484.
Freudenberg K, Cramer F. Die Konstitution der Schardinger Dextrin alpha, beta dextrin, and gamma[J]. Zeitschrift Fur Naturforschung Section b — A Journal of Chemical Sciences, 1948, 3: 464–466.
Harada A. Cyclodextrin-based molecular machines[J]. Acc Chem Res, 2001, 34(6): 456–464.
Singh R, Bharti N, Madan J. Characterization of cyclodextrin inclusion complexes: A review[J]. Journal of Pharmaceutical Science and Technology, 2010, 2(3): 171–183.
Wang G H, Xu W D, Wang X G et al. Glycine-β-cyclodextrin-enhanced electrokinetic removal of atrazine from contaminated soils[J]. Environmental Engineering Science, 2012, 29(6): 406–411.
Cai X Y, Liu W P, Chen S W. Environmental effects of inclusion complexation between methylated β-cyclodextrin and diclofop-methyl[J]. Journal of Agricultural and Food Chemistry, 2005, 53(17): 6744–6749.
Bhesh R B, Bruce R D, Indra P. Encapsulation of lemon oil by paste method using β-cyclodextrin: Encapsulation efficiency and profile of oil volatiles[J]. Journal of Agricultural and Food Chemistry, 1999, 47(12): 5194–5197.
Mao Y, Sun M, Yang X. Remediation of organochlorine pesticides (OCPs) contaminated soil by successive hydroxypropyl-β-cyclodextrin and peanut oil enhanced soil washing-nutrient addition: A laboratory evaluation[J]. Journal of Soils and Sediments, 2013, 13(2): 403–412.
Petrovic G, Stojanovic G, Palic R. Modified β-cyclodextrins as prospective agents for improving water solubility of organic pesticides[J]. Environmental Chemistry Letters, 2011, 9(3): 423–429.
Perez-Martinez J I, Gines J M, Morillo E. Improvement of the desorption of the pesticide 2,4-D via complexation with HP-β-cyclodextrin[J]. Pest Management Science, 2000, 56(5): 425–430.
Torres P, Villa F, Gonzalez J. Preparation and characterization of the emamectin benzoate/hydroxypropyl-β-cyclodextrin inclusion complex[J]. Journal of the Chilean Chemical Society, 2011, 56(4): 951–954.
Ge X, Huang Z, Tian S L. Complexation of carbendazim with hydroxypropyl-β-cyclodextrin to improve solubility and fungicidal activity[J]. Carbohydrate Polymers, 2012, 89(1): 208–222.
Wang Jia, Feng Jianguo, Ma Chao. Technology of cyclodextrin and its application in pesticide formulation processing[J]. Chinese Journal of Pesticide Science, 2013, 15(1): 23–31 (in Chinese).
Streibig J C. Herbicide bioassay[J]. Weed Research, 1988, 28(6): 479–484.
Santelmann P W. Herbicide Bioassays[M]. In: Research Methods in Weed Science. Truelove B ed. Southern Weed Science Society, Auburn University, Auburn, USA, 1977. 80–87.
Gunther P, Rahman A, Pestemer W. Quantitative bioassays for determining residues and availability to plants of sulfonylurea herbicides[J]. Weed Research, 1989, 29(2): 141–146.
Higuchi T, Connors K A. Phase-solubility techniques[J]. Adv Anal Chem Instr, 1965, 4(1): 117–212.
Zhang Ping, Zhang Jinyan. The effect of atrazine cyclodextrin inclusion on barnyard grass seedlings weeding[J]. Journal of Heilongjiang Bayi Agricultural University, 2011, 23(3): 13–15 (in Chinese).
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Supported by the National Natural Science Foundation of China (No. 31370709).
Zhang Jinyan, born in 1968, female, Dr, Prof.
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Zhang, J., Li, B., Bi, H. et al. Synthesis of atrazine-HPCD inclusion and its bioactivity. Trans. Tianjin Univ. 20, 350–357 (2014). https://doi.org/10.1007/s12209-014-2401-9
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DOI: https://doi.org/10.1007/s12209-014-2401-9