| 1,4-dien-3-one analogues have similar structural characteristics as curcumin,the stability is better than curcumin,with a wide range of biological activities,for example antiviral,anti-inflammatory,anti-cancer,anti-oxidation,insecticidal,antimicrobial and antitumor,weeding and so on.Therefore,the synthesis of 1,4-dien-3-one derivatives become a hot research at home and abroad.In addition,heterocyclic compounds,especially nitrogen heterocyclic compounds in present research and development of pesticide occupy the important position,the introduction of heterocyclic compounds tend to significantly improve the physical and chemical properties and biological activity.Oxime esters compounds is a kind of important active compounds with insecticidal activity,antibacterial,antiviral,weeding and other biological activity,and most of the oxime ester compounds have high efficiency,low toxicity and low residue.For this reason,they have received extensive research for a long time.According to current situation,in order to research for highly active compounds,curcumin was modified by active functional group oxime ester with biologically active factor splicing of asymmetric 1,4-dien-3-one derivatives,40 novel compounds were synthesized through etherification,oximic reaction and esterify reaction.The structure was identified by IR,1H NMR,13 C NMR spectra and MS.The growth rate method was used to evaluate antifungal activity of all compounds,at the reagent concentration of 50 μg/mL,the result of bioassay showed that most of the compounds have certain antifungal activity.compounds I23,II3,II8,II9 showed inhibition against G.zeae on rate of 42.8、45.2、45.6、48.3% respectively,lower than to kresoxim-methyl(54.3%);compounds I19,I26,II2,II12 showed inhibition against B.Cinerea on rate of 51.2,63.6,52.4,51.4% respectively,which were inferior to kresoxim-methyl(70.3%);compound II4 showed inhibition against R.solani on rate of 50.9%,which kresoxim-methyl was 63.6%.The turbidity method was used to evaluate bacteriostatic activity of all compounds,at the reagent concentration of 200 μg/mL and 100 μg/m L,the result of bioassay showed that most of the compounds have certain bacteriostatic activity.At the reagent concentration of 200 μg/mL,compounds I21,II7,II11 showed inhibition against X.oryzae on rate of 89.4,93.1,79.3% respectively,which were higher than Bismerthiazol(77.5%);at the reagent concentration of 100 μg/m L,compounds I20,II7 showed inhibition against X.oryzae on rate of 68.3,85.2% respectively,which were higher than Bismerthiazol(56.4%);At the reagent concentration of 200 μg/mL,compounds I22 showed inhibition against R.solanacearum on rate of 92.4%,paralleled to Bismerthiazol(94.1%);At the reagent concentration of 200 μg/mL,compounds I3,I14,I16,I18,II1,II2,II7 showed inhibition against X.citri on rate of 81.8,83.4,80.9,76.8,86.8,81.3,81.2% respectively,which were higher than Bismerthiazol(80.4%);at the reagent concentration of 100 μg/m L,compounds I3,I14,I16,I18,II7 showed inhibition against X.citri on rate of 81.8,83.4,80.9,76.8,67.2% respectively,which were higher than Bismerthiazol(63.2%);The Half-leaf method was used to determine the in vivo efficacy of the title ompounds against TMV,and the results of bioassay showed that a part of compounds exhibited moderate anti-TMV activities at the concentration 500 μg/m L.compounds I5,I12,II1 displayed curative activity on rate of 58.8,59.2,53.7% which were higher than Ningnanmycin(51.8%);compounds I20,I25,II4,II6,II7 displayed protective activity on rate of 65.1,66.3,62.2,64.9,64.8%,paralleled to Ningnanmycin(65.7%);compound I5 display inactivation activity on rate of 70.8%,which was lower than Ningnanmycin(95.8%). |
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