Studies On Synthesis And Properties Of Spiro-heterocyclic Compounds With Biological Activities

In the 21st century, pesticide must have the characteristics of high efficiency, low toxicity, economy and good environmental profile. In recent years, heterocyclic compounds have become the mainstream in new pesticide discovery, and more than 90%of patented pesticides in the world are about heterocyclic compounds, because of their biological activities features of broad spectrum and high efficiency. Spiro-heterocyclic compounds are important branch of heterocyclic compounds, and play an important role on today's research and development of pesticides and medicines.The recent research and development of pesticide containing a spiro structure, spirocyclic tetronic acids were reviewed in this thesis.27 novel spiro-heterocyclic compounds were designed and prepared by using spirocyclic tetronic acids with biological activities as lead compounds based on pesticide molecular design technologies, such as connection of sub-structures and bioisosterisms. These compounds can be divided into two series as followings:(â… ) 2-oxo-3-o-tolyl-1-oxaspiro[4.5]dec-3-en-4-ol derivatives (â… a-â… m).(â…¡) 2-oxo-3-o-tolyl-1-oxaspiro[4.4]non-3-en-4-ol derivatives (â…¡a-â…¡n).Synthesis methods for intermediates and target compounds were studied, and the structures of the prepared compounds were confirmed by IR,1H NMR and LC/MS.The bioassays of preliminary biologic activity were carried out according to the standard operation procedure of pesticide bioassay. The results showed that compoundsâ… and Compoundsâ…¡exhibited different extent of insecticidal activity, for example, at the concentration of 1000 mg/L, all of compoundsâ… a,â… ,â… e andâ… m possessed 100% lethality rate against Oriental Armyworm, Its insecticidal activity is higher than spirodiclofen. Compound I f exhibited 95%lethality rate,this is equival as spirodiclofen's.at the concentration of 500 mg/L, compoundsâ… b,â… g andâ… l showed 97.5%,97.22%and 98.99% lethality rate against Aphis fabae, Its insecticidal activity is a little higher than spirodiclofen" s. compoundsâ… d,â… g, andâ… m exhibited 97.06%, 92.37%and 97.16%lethality rate against Tetranychus urticae. Its insecticidal activity is slightly higher than spirodiclofen's.In general, compoundsâ… have relatively high insecticidal activity.Compoundsâ…¡also exhibited different extent of insecticidal activity, for example, at the concentration of 1000 mg/L, bothâ…¡a andâ…¡j exhibited 100%lethality rate against Oriental Armyworm, Its insecticidal activity is higher than spirodiclofen. Compoundâ…¡e,â…¡l possessed 95%,95.45%lethality rate,this is equival as spirodiclofen" s. at the concentration of 500 mg/L, Compoundâ…¡b,â…¡e,â…¡l,â…¡a,â…¡c andâ…¡i showed 100%,100%,100%,98.57%,99.44%and 97.46%lethality rate against Aphis fabae, Its insecticidal activity is a little higher than spirodiclofen's. compoundsâ…¡d andâ…¡g showed 89.02%and 88.56% lethality rate against Tetranychus urticae. Its insecticidal activity is slightly higher than spirodiclofen's.In general, compoundsâ…¡have also relatively high insecticidal activity.