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Synthesis And Bioactivity Study Of Pheromone Analogs Of Diamond Back Moth Plutella Xylostella

Posted on:2018-01-12Degree:MasterType:Thesis
Country:ChinaCandidate:K X ZhangFull Text:PDF
GTID:2333330518484786Subject:Pesticides
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The development of pheromone analogs will help to solve a series of problems in the use of insect natural pheromones,such as fast degradation and poor stability in field condition,high cost of chemical synthesis and risk of pheromone resistance,and improve the field effect of semiochemicals.Diamondback moth Plutella xylostella L.is a very important pest of cruciferous vegetables.And studies on pheromone analogs of diamondback moth were conducted in several decades,ranging from alcohols,aldehydes and acetates of the sixteen carbon compounds to cyclopropane and halo analogs of sex pheromone components.Our laboratory also had screened three sex pheromone analogs with potential communication disruption activity by the end of last term,which were?Z?-hexadec-11-en-1-yl 2,2,2-trifluoroacetate?1?,?Z?-hexadec-11-en-1-yl 2,2,3,3,3-pentafluoropropanoate?2?,?Z?-hexadec-11-en-1-yl trifluoromethanesulfonate?3?.Firstly,bioactivity of three pheromone analogs was carried out in field in order to evaluate the directional interference of P.xylostella male to sexual attractant or conspecific female.The results showed that the rate of mating disruption was over 92%when analog 1 and 2 mixed with the pheromone in a 1000:100 ratio,in which the biological activity of the analog 1 was more excellent and stable.Secondly,according to the chemical structure modification strategy of Lepidoptera insect pheromone,a total of twenty-seven pheromone analogs were designed and synthesized in this paper,including pheromone analogs with"trans"configuration,unsaturated bond or carbamate group in the polar group.Among them,nineteen compounds were novel pheromone analogs,and the chemical structures of all compounds were confirmed by 1H NMR,13C NMR and HRMS.By measuring EAG response to these pheromone analogs,EAG response to pheromone components Z11-16:Ald and Z11-16:Ac after pre-saturated with these pheromone analogs and degradation capacity of pheromone-degrading enzyme?PDE?to Z11-16:Ald and Z11-16:Ac after pre-incubation with pheromone analogs,four pheromone analogs with excellent biological activity which were analog 4,5,6,and 9a were screened.The inhibition rate of EAG response to pheromone components after pre-saturated with analog 4,5,6,9a was 29.63%-63.07%at the dose of 100?g,and the inhibition rate of metabolic capacity of pheromone-degrading enzyme after pre-incubation with these pheromone analogs was 59.66%-95.28%at the concentration of 300?M.Based on our results,we would expect to find semiochemicals with good activity to control P.xylostella,and also would hope to provide a theoretical basis for clarifying the chemical communication mechanism of P.xylostella.
Keywords/Search Tags:Plutella xylostella, Pheromone, Pheromone Analog, Behavior-manipulated strategies, Bioactivity
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