Synthesis Of Monoterpene Oxabicyclodiol And Biological Activity Of Its Derivatives

Synthesis and biological activity of heterocyclic compounds has always been one of the most active and important research subjects in the organic chemistry,pesticide chemistry and medical chemistry.Heterocyclic compounds have found wide application in the fields of medicine and pesticides because of their good bacteriostatic and antifungal bioactivities.In our recently preliminary study the monoterpene oxabicyclodiol{(3R,4R)-4,7,7-trimethyl-6-oxabicyclo[3.2.1]octane-3,4-diol,compound 1}were synthesized from?-pinene by one step catalytic method.Preliminary studies found that compound 1 and its derivatives have adjustable hydrophilicity and obvious herbicidal activities against ryegrass,may be prepared into environmentally water-base herbicide.However,the complicated processs for preparing catalyst,the violent reaction process and poor yield for synthesis of compound 1,the unclear catalytic mechanism of compound 1 derive from?-pinene and the incomplete biological activity of compound 1 and its derivatives are not good for further development and application of these compounds.The main research contents of this paper are as follows.(1)According to the stoichiometric reaction,serial peroxyphosphotungs-tomolybdates were synthesized by using H₂WO₄,H₂Mo O₄,H₃PO₄ and hexadecylpyridinium chloride as raw materials via one-pot synthetic method.In order to improve conversion rate of?-piene and selectivity to compound 1,the relationship between elementary composition and catalytic performance were studied by measuring the spectral properties?elementary composition and acid value on FT-IR?UV-Vis?ICP-AES and potentiometric titrator,respectively.(2)Using the intermediates epoxypinane and sobrerol detected by GC and GC-MS among the reaction process as marials,and reacting in same system to confirm the reaction mechanism of compound 1 derive from?-pinene by one step catalytic method.(3)The single crystals of compound 1 and its derivatives(2a,4a,6a,8a)were grown by slow evaporation method and determined by single crystal X-ray diffraction analysis.(4)The herbicidal activities of compound 1 and its derivatives 2a-3d against root growth and shoot elongation of rap,barnyard grass and velvetleaf were investigated by petri dish method and beaker method,respectivily.The results showed that compound 1 and its derivatives exhibited obvious inhibition activities against the growth of root and shoot of rap,barnyard grass and velvetleaf,and all derivatives have better herbicidal activities than compound 1.(5)The antibacterial activity of compound 1 and its derivatives 2a-3d against five bacterias and three funguss were studied by filter-paper method.The results indicated that compound 1 and its derivatives have no obvious activity against all the tested bacterias and funguss.