Synthesis of potential plant protecting compounds on the basis of 2,3-dihydrothiazol-2-thione. I. Change in structure at the N-3 and C-4

A considerable number of potential plant protecting compounds with the core structure of 2,3-dihydrothiazol-2-thione has been prepared by the reaction of dithiocarbamates with halomethylcarbonyl compounds forming N-substitute d 4-substituted 4-hydroxythiazolidin-2-thiones 2-4, which can split off wat er to yield 5. The structural variability at Ng is given either by the amin e used for dithiocarbamate synthesis or by acylation of N-unsubstituted 2,3 -dihydrothiazol-2-thiones like 4i. The variability at C-4 is either achieve d by the kind of the halomethylcarbonyl compound or by reactions of 4-chlor omethyl derivatives 5, which can be transformed by a number of nucleophilic reagents to derivatives like thioethers 8, ethers 9, amines 10, nitriles 1 1, azides 12a, thiocyanates 12b, the primary amine 14 and derived from that the amides 15 or the ureas 16.