Synthesis And Insecticidal Activity Of Derivatives Of Terpinen-4-ol And It's Analogues

Natural lead compounds linking with active substructure is a main way to research and develop new pesticide. Terpine-4-ol, Carvone and menthone all exhibited certain insecticidal activity, and modifyied easily. oxime ether structure is also a kind of effective groups often to be chosen to create new pesticides, the oxime ether componds synthesized easily with the monoterpene counting carbonyl. In order to find the high active derivatives of terpinen-4-ol, 20 derivatives were synthesized with terpinen-4-ol in this research, carvone and menthone. The chemical structure of compounds were confirmed and their fumigation and contact activity were tested. Main results showed as follows:1. 20 derivatives were synthesized with terpinen-4-ol, carvone and menthone. The structures of the 20 derivative compounds were confirmed by GC-MS,1H-NMR,13C-NMR and IR. There are 14 derivatives are new compounds and haven't been reported before.2. The contact activity of the 20 derivatives against Mythimna separata W. were tested through'Capillary vessel drip method', the results showed that 20 compounds all exhibited certain contact activity, mong which WM1, WM2 and WM8 was significantly higher than terpinen-4-ol and their analogs carvone and menthone with LD50 of 0.0054mg/insect, 0.0217 mg/insect, 0.009mg/insect.3. The fumigation activity of the 20 derivatives against Mythimna separata W. were tested, the results showed that 15 compounds(WM1^WM14 and S2) exhibited certain fumigation activity but lower than their parent compounds, among which WM5 had the highest activity with LC50 of 1.35μL/L, The fumigation activity of WM5 equivalent to terpinen-4-ol and menthone.4. The fumigation activity of the 20 derivatives against Musca domestiea L were tested, the results showed that 15 compounds(WM1-WM14 and S2) exhibited certain fumigation activity but lower than their parent compounds, among which WM5 had the highest activity with LC₅₀ of 7.6239μL/L.5. Qualitative structure-activity relationship showed that the contact activity of oxime ethers derivatives are related to the structure of halogenated hydrocarbons, contact activity decreases with the lack of electronic degree of halogenated compounds.