Studies On Biologically Active Heteroatomic Organic Compounds (V)

Imidazolones, one of the most flourish in the research and development of agrochemicals , have been found to be used as herbicide , fungicide , etc. and have the applied foreground extensively . In this paper , according as the connecting principle of biological activity group, allyl or propargyl groups were connected with imidazolone, the novel imidazolone with allyl or propargyl group , eighteen unreported imidazolone derivatives in two series , were synthesized with mild condition and good yields . The reaction condition , spectral properties and biological activities of the imidazolone derivatives with allyl or propargyl groups were also studied , and some of them were found to show good herbicidal and fungicidal activities . It may be summarized as follows :1. The cyclization reaction of the primary allyl-typed amines with the mediate (M4) in no presence of solid potassium carbonate was reserched firstly . The result showed that it was a good method for preparation of mediates (M5) , 2-thio-3- allyl-typed alkyl-5-(4-methyloxyphenylmethylidene)-4-imidazolidinones.2. The S-alkylate of 2-thio-3-allyl-typed alkyl-5-(4-methyloxyphenylmethylid -ene)-4-imidazolidinones (Mi) with allyl or propargyl bromide in presence of dry solid potassium carbonate (K2CO3 : CH2=CHCH2Br = 1 : 1.2 - 6(mol)) was researched firstly , and the target compounds (2-allyl(or propargyl)thio -3-allyl-typed alkyl-5-(4-methyloxyphenylmethylidene)-4H-imidazolin-4-ones) , were conveniently synthesized at 12-40 ℃ .3 The spectral and physical properties of the target compounds( I and II) were studied systematically.4 The biological activities of the target compounds( I and II) were tested .The results showed propargyl group in novel midazolones( II) contributed to herbicidal activities . In 100ppm , E3 , II6 , II7 and I9 exhibited 87.5% , 70.5% , 78.4% and 62.5% inhibition of Cole root; I 9 exhibited 71.4 % inhibition of Stalk of barnyard grass . In 10 ppm , I 4 promoted slightly growth of Cole root; In 10 ppm or 100 ppm, i6 promoted slightly growth of Stalk of barnyard grass.