Synthesis And Biological Activities Of 2- Alkyloxy -2-Phenylethyl Sultide Compounds

Sulfur exists on the earth widely and it is a kind of important element which constitute lives. It has been thousands of years for human beings using sulfur or sulfur compounds. Sulfur compounds is used widely on pesticides, pharmaceuticals, chemical dyes and functional materials with the development of modern science. Sulfur atoms are present as C-S bond in organic compound. Mercaptan and thioether compounds are the most popular. Thioether receives a lot of attention because the widely using on medicine, dye and new materials.2-bromoacetophenone, phenthiol and its derivatives were used as fundamental raw materials.30 kinds of different structures’ new 2-alkyloxy-2-phenylethyl sulfide compounds were designed and synthesized in this paper. A rather complete biological activities were determined.9 screened compounds showed activities against Heterodera glycines.4 screened compounds showed activities of hindering seed germination against Abutilon theophrasti and Amaranthus retroflexus.4 screened compounds showed broad-spectrum antimicrobial activity.4 screened compounds could inhibition oomycetes.4 screened compounds showed high inhibition rate of Rhizoctonia solani.2-bromoacetophenone, phenthiol and its derivatives were used as fundamental raw materials.30 kinds of 2-alkyloxy-2-phenylethyl sulfide compounds were got after substitution, reduction, substitution and other reactions. Every kind of compound we got was characterized with the methods of 1H NMR and GC-MS. Results showed that spectrum matched compound structure very well.The activities against soybean cyst nematode were tested by dipping method with the 30 kinds of compounds. It come out that M1-3, M7-3, M17-3, M28-3, M29-3 and M30-3 with 50 μg/mL in 72 h, the death rate can reach 100% and showed high activity.The activities against insects were tested by dipping and Slide-dip methods with 30 kinds of compounds on Martianus dermestoides, Galleria mellonella, Calliptamus abbreviatus, Musca domestica and Aphis citricola. It showed that there was little activity against insects.The herbicidal activities were tested by seed germination experiments with 30 kinds of compounds on Echinochloa crusgalli, Digitaria sanguinalis, Abutilon theophrasti and Amaranthus retroflexus. Screening again after preliminary screening among the compounds which herbicidal activities were above 70%. Seed germination experiment showed that M2-3, M7-3, M18-3 and M33-3 had significant herbicidal activities with 100,20 and 4 μg/mL against A. theophrasti and A. retroflexus.The antibacterial activities were tested by mycelium growth rate with 30 kinds of compounds on Botrytis cinerea, Rhizoctonia solani, Exserohilum turcicum, Helminthosporium sorokinianum, Phytophthora capsici, Corynespora cassiicola, Pyricularia oryzea, Fusarium oxysporum. The compounds which inhibition rate was above 50% with 50 μg/mL were selected to test toxicity. It showed that M7-3, M17-3, M33-3 and M34-3 had better activities against R. solani. M18-3,M 19-3 and M20-3 show significantly inhibition on oomycete. M1-3, M2-3, M30-3 and M31-3 showed extensive antibacterial effect. In the virulence test, the compounds’ EC50 were lower than 60 μg/mL against corresponding germs.They have certain development potential.In this paper, we studied synthesis and biological activities of 2-alkyloxy-2-phenylethyl sulfide compounds and provided a new valuable lead compouds. And set a foundation for the further research.