Synthesis And Biological Activity Of 1,3,4-thiazolidine Derivatives Containing Trifluorobutene

In this paper, C. elegans and T. semipenetrans as the research object, using Fluensulfone as the lead structure. A series of 1,3,4-ox?thi?adiazoles derivatives containing the trifluorobutens thioether?sulfone? group were designed and synthesized. The nematicidal activities of the target compounds was screened in vitro and some of the title compounds exhibited excellent nematicidal activities against C. elegans and T. semipenetrans. The results could be summarized as follows:1. As the guide structure of Fluensulfone, we considered the possibility of introducing trifluorobutens moiety into substitutedphenyl-1,3,4-ox?thi?adiazoles scaffold. A total of 52 novel 1,3,4-ox?thi?adiazoles derivatives containing the trifluorobutens thioether?sulfone? group were designed and synthesized, the structures of all the target compounds were elucidated by elemental analysis, IR, 1H NMR and 13 C NMR spectra.2. The title compounds were evaluated for their nematicidal activities in vitro, fosthiazate as control agents. The results of bioassay showed that compounds B9 and D7 exhibited higher nematicidal activity against C. elegans, with correction mortality of 100% and 92.07%, after 24 h of treatment at 200 ?g/m L, respectively. Compounds A₁, A₁3, B2, B5, C₁, C5 and D7 against second juveniles of C. elegans with correction mortality of 91.58%, 94.08%, 91.86%, 94.63%, 96.56%, 99.28%, 100%, respectively, after 48 h of treatment at 200 ?g/L. Especially compounds A₁, A2, A5, B2 and B8 showed significantly higher nematicidal activities against C. elegans, with LC50 values of 21.92 ?g/mL, 69.89 ?g/m L, 64.07 ?g/m L, 44.94 ?g/m L, 66.75 ?g/m L, respectively, after 48 h of treatment, which were superior to that of fosthiazate?100.78 ?g/L?.3. Some of title compounds were evaluated for citrus nematode activity in vitro, fosthiazate as control agents. The results showed that compounds A2, A5, B2, B4 and B9 exhibited moderate activity against citrus nematode?T. semipenetrans? with correction mortality of 79.99%, 74.50%, 78.59%, 75.96%, 73.15%, respectively, after 48 h of treatment at 100 ?g/m L, than fosthiazate?67.93%?. The most of compounds showed good nematicidal activity and had higher than 80% correction mortality at 100 ?g/mL, after 72 h of treatment.