Studies On Biologically Active Heteroatomic Organic Compounds(â… )

Pyrethroid insecticides are developed from lead compounds that are the effective components extracted from natural pyrethrum flowers. As a class of bionic insecticide, a great of progress has been achieved in their synthesis, action mechanism and so on in the last thirty years. This dissertation summarizes the recent studies.In order to explore novel pyrethroid insecticides, improving their hydrophilic activity we designed and synthesized three series of new pyrethroid compounds containing phosphonyl and heterocycloamino group. Their structures were characterized by IR, 1H NMR, MS spectroscopes. Formulas of target compounds were illustrated as follows:In the course of preparing these compounds, 2-(4-chlorophenyl)-3 -methyl-but-yric acid was first converted to butyryl chloride by thionyl chloride, then butyryl chloride reacts with a-hydroxylalkylphosphonates, a-aminoalkylphosphonates and heterocycloarnines. The reaction conditions are mild and the yields are good.In IR spectra, carbonyl(C=0) and phosphonyl (P=0) appeared as very strong absorbing peak at 1700cm"1 and 1250cm"1 or so respectively. In !H NMR spectra, that the free spin of P-O-C bond and CH-CH bond is blocked can be observed because of big substituted group. In MS spectra, generally, molecular ion peak can be observed with low intensity. Fragmentation mainly occurs between carbon and oxygen of acyloxyl C(O)-O or carbon and nitrogen of amido C(O)-N . In most compounds, fragment of m/z = 125 is common.Preliminary bioassay showed that some of them have acaridcidal and fungicidal activities. Acaridcidal activities of compounds 4c, 4e, 4g, 4i reach to the grade of A. They can be further investigated as lead compounds.