Synthesis and biological activity of N-alkyl-6-(3-chloro-4-chloromethyl-2-oxopyrrolidin-1-yl)-7-fluoro-3,4-dihydro-2H-1,4-benzoxazin-3-one derivatives

In order to find novel pesticides with high activities, low toxicities and low residues, sixteen novel N-alkyl-6-(3-chloro-4-chloromethyl-2-oxopyrrolidin-1-yl)-7-fluoro-3,4-dihydro-2H-1,4-benzoxazin-3-one derivatives 6a similar to 6p were designed and synthesized. Their structures were confirmed by IR, H-1 NMR, LC/MS spectra and elemental analysis. The results of preliminary bioassay indicated that some title compounds exhibited obvious biological activities, for example, compounds 6c similar to 6f showed more than 90% herbicidal activities against Abutilon theophrasti, Amaranthus spinosus and Chenopodium album L. at 150 g/hm(2), and compounds 6l and 6o exhibited more than 90% insecticidal activities against Aphis fabae at 500 mg/L. It was also revealed that compounds 6d and 6e exhibited not only good herbicidal activities but also excellent insecticidal activities.