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Synthesis and Biological Activity of Polyethylene Glycol Phenoxyacetate and Inclusion Compounds with β-cyclodextrin

Author: LiZuoZuo
Tutor: WeiTaiBao；ZhangYouMing
School: Northwest Normal University
Course: Organic Chemistry
Keywords: PEG aromatic oxygen acid β-cyclodextrin Supramolecular inclusion complex new plant growth regulator
CLC: O636.1
Type: Master's thesis
Year: 2011
Downloads: 95
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Abstract


Supramolecular chemistry is the science of the intermolecular bond, covering the structures and functions of the entities formed by associasion of two or more chemical species. Cyclodextrin is one of the most important host of poly (pseudo) rotaxanes, assembly between cyclodextrin (CD) and Polymer have attracted growing attention due to their selectivity, regulation, control and biocompatibility.Aryloxycarboxylic acid and its derivatives, such as ester, amide, hydrazide, quaternary ammonium and alkali metal salts etc., because of its low price, easy preparation, have became a series of widely used plant growth regulators. They can impact on plant growth and develop strong physiological activities, trace of them also can obviously stimulate plant growth and increase yield.PEG [poly (ethylene glycol), PEG] has a good water-soluble, biocompatible, non-toxic and wide molecular weight, especially after bonding with other substances can fully display its advantages. Meanwhile, seeds coped with polyethylene glycol (PEG) treatment can improve seed germination rate and seedling vigor. It is very significant to early emergence, nurturing seedlings and production increasing. However, considering the lower reactivity of hydroxyl group of end of the PEG chain, usually needs to be functioned. According to superposition principle of activity group, after two or more active elements are connected in a molecule, its biological activity tends to strengthen or lead to a new generation. The use of polyethylene glycol on a variety of biologically active compounds can be modified to search for new plant growth regulator to provide more optional objects. This study chose a simple and subject-object system(β-cyclodextrin and polyethylene glycol supramolecular system), using different methods to alter the end groups of PEG, designed by the aromatic acid and oxygen synthesis polymers of polyethylene glycol PEG aryloxycarboxylic acetate, and then react withβ-cyclodextrin to format the active ingredient combination of the three polymer supramolecular polymers which verified by infrared spectroscopy(FTIR), nuclear magnetic resonance(1HNMR), differential Thermal analysis(DTA), but also made a preliminary study of the object and the inclusion to growth regulator performance of the rapeseed plant.This thesis includes three chapters:Chapter 1: Synthesis, characterization and biological activities acetate of Polyethylene glycol 600 aryloxycarboxylic. We have developed di-chloroacetic acid ester of polyethylene glycol 600 with chloroacetyl chloride and polyethylene glycol 600, and then made different phenols react with di-chloroacetic acid esters of polyethylene glycol 600 pairs in acetone by oxygen alkylation to develop a series of aryloxycarboxylic acetate of polyethylene glycol 600. Through the study of different solvents we found acetone is most suitable solvent as inexpensive and easy to gotten. The preliminary biological activity tests showed that both aromatic oxygen acetic acid and polyethylene glycol two kinds of active units have the active sub-stack effect. Some of the series of the compounds in a certain concentration have the significant role in promoting the rapeseed root and better than that of IAA, in which p-chlorophenoxy acetate of polyethylene glycol at a concentration of 0.01mg / L, the role of rape seedlings to promote the best to promote the rate of 386%, so they have been high activity, low toxicity, environmental compatibility, and can be used as a new plant growth regulator.Chapter 2: Synthesis, characterization and biological activities of acetate of Polyethylene glycol 6000 aryloxycarboxylic.We have prepared the different methods to carry out the esterification reaction with aryloxycarboxylic chloride and polyethylene glycol, and conveniently obtained aryloxycarboxylic acetate of polyethylene glycol 6000 in high field. Accroding to the first series of methods we explored the growth regulator of rapeseed plant. Biological activity tests show that: at a concentration of 0.1 ~ 0.001mg / L, bio-activity of the o-methyl phenoxyacetate of polyethylene glycol 6000 (2b), m-ethyl phenoxyacetate of polyethylene glycol 6000 (2c), are obviously better than the raw material o-methyl phenoxyacetic acid (1b), m-ethyl-phenoxyacetic acid (1c), and polyethylene glycol 6000 and indole acetic acid.Chapter 3: Synthesis, characterization and biological activity of Cyclodextrin inclusion complexes.We have used host moleculeβ-cyclodextrin with guest molecules of aryloxycarboxylic acetate of polyethylene glycol 6000, reacted in ethanol / water interaction and prepared a series of solid aryloxycarboxylic inclusion complexesβ-cyclodextrin-polyethylene glycol acetate. Inclusion complexes not only have Slow -release effect of CD and promoted the effectiveness of plant yield, but also both have better stability, chemical adjustability and solubility. The preliminary biological activity tests show that the inclusion complexes have obvious regulating activities for the growth of the rape seed, is better than polyethylene glycol aryloxycarboxylic acetate andβ-CD. At a concentration of 0.1 ~ 0.001mg / L, inclusion complexes (IC-2g, IC-2h) the promotion of the role of rape root length is significantly better than the 2g, 2h, andβ-CD, the promotion rate reached 81.3%, 81.7%, is an excellent plant growth regulator.

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CLC: > Mathematical sciences and chemical > Chemistry > Polymer chemistry ( polymer ) > Natural polymers ( polymer ) > Polymer polysaccharides
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