THE SYNTHESIS OF SOME 3-AMINO-2-HALOMETHYLQUINAZOLIN-4(3H)-ONES, 2-HALOMETHYL-3-(SUBSTITUTED-AMINO)QUINAZOLIN-4(3H)-ONES AND 2-HALOMETHYL-3-HETARYLQUINAZOLIN-4(3H)-ONES AS POTENTIAL PLANT PROTECTING AGENTS

A series of N(2)-(2-halomethyl-4-oxo-3,4-dihydroquin-azolin-3-yl) carbazates 4 and 5 and 2-halomethyl-3-hetarylquinazolin--4-(3H)-ones 8 and 9 were obtained by reacting 2-halomethyl-4H-3,1-benzoaxin-4-ones (12) with alkyl carbazates and hetarylamines, respectively. Some of the carbazates 4 and 5 were obtained alternatively, by treatment of N-(2)-(2-aminobenzoyl)carbazate 15 with haloacetyl halides. The t-butyl carbazates 5 were converted into 3-amino-2-halomethylquin-azolin-4(3H)-ones (6), some of which were further converted into 3-(2,5-dimethylpyrrol-1-yl)-2-halomethylquinazolin-4(3H)-ones (7). 3-Amino-2-bromomethylquinazolin-4(3H)-one (6b) was also obtained by brominating its 2-methyl analogue 1 with cyanogen bromide.