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Study On Synthesis And Fungicidal Activity Of Novel Methoxyacrylate Derivatives

Posted on:2011-11-28Degree:MasterType:Thesis
Country:ChinaCandidate:Y H GaoFull Text:PDF
GTID:2181330332485422Subject:Applied Chemistry
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The strobilurins are an outstanding new class of agricultural fungicides, and this class of fungicides is based on a group of natural lead derivatives of (E)-methyl B-methoxyacrylate ,such as strobilurin A, oudemansin A and myxothiazol A. These fungicides can strongly inhibit mitochondrial respiraton by blocking electron transfer at the ubiquinol-oxidation centre of the bc1 enzyme complex. With their broad spectrum of activity, long duration of action, high activity at low rates of application, and outstanding environmental tolerability, the strobilurins have been one of the most important classes of agricultural fungicides, and their wide application showed it is very important to design and synthesize new strobilurin similar compounds with higher biological activity.Sesamol is an important natural organic phenol, which has strong antifungal bioactivity and remarkable antioxidant activity. It is an import antintermediates in the pesticide and the pharmacology too.In order to develop novel fungicides with high activities, the side chain and pharmacophore of the strobilunrins derivatives were optimized from the commercialized strobilurins and high bioactive compounds the literature reportded, by the means of the active structural stitching and the bioisosterism, the results are as follows:1.The strobilurin derivatives are summarized in this thesis, and the review describes in detail their structure of natural structure, history of develoment, structure optimization, synthesis methods,biochemical mode of action and resistance risk.2.An important intermediate of strobilurin,(E)-2-(2-methoxyimino)-2-(bromomethyl) Benzeneacetates was synthesized from 2-benzoic acid, via Friedel Crafts acylation, cyanidation, hydrolysis, esterification , oximation and bromination.3. With sesamol as the starting material, a series of sesamol derivatives were synthesized through acylation, oximation, etherification and nitration of phene moiety.4.Two kinds of strobilurins, 20 new compounds totally, were synthesized, and their structures were elucidated mainly based on 1HNMR and IR,and they are not reported at all.5.With Amistar as positive control, the fungicidal activities of all the target compounds against G. cingulata, F. graminearum, B. cinerea, P.capsici Leonian were investigated through mycelium growth rate, the results indicated that two strobilurins derivatives showed good activities.
Keywords/Search Tags:strobilurin, sesamol, antifungal activity
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