PREPARATION AND PLANT GROWTH-REGULATORY ACTIVITY OF N'-CHLORO-SUBSTITUTED PHENYL-N-FURFURYLOXAMIDE AND BENZYL-N-FURFURYLOXAMIDE

N'-Chlorophenyl- and N'-chlorobenzyl-N-furfuryloxamides (6b-e and 7b-d ) were synthesized through the reaction of chloro-substituted anilines (12b-e) or chloro-substituted benzylamines (13b-d) with N-furfuryloxa mic acid sodium salt (10), which was prepared via condensation of meth yl oxalate (8) with furfurylamine, followed by hydrolysis of the resul ting amide-ester with sodium hydroxide, The activity of the prepared c ompounds (6 and 7) as plant growth regulators was examined by a germin ation assay using rape and leek seeds. N'-(3-Chlorophenyl)-N-furfurylo xamide (6c) showed a little effectiveness as an inhibitor, whereas the parent compound, N'-phenyl-N-furfuryloxamide (6a) inhibited the root growth of rape seedlings, The 2-chlorophenyl derivative (6b) inhibited the root growth of rape seedlings as potently as 6a, but sufficiently promoted the root growth of leek seedlings. Further, the 4-chlorophen yl derivative (6d) promoted the root growth of both species. On the ot her hand, in the series of chlorinated benzyl derivatives (7b-d), N'-( 3-chlorobenzyl)-N-furfuryloxamide (7c) showed a markedly superior inhi bitory effect in both species, but 2- and 4-chlorobenzyl derivatives ( 7b and 7d) inhibited the root growth of only rape seedlings.