[Trichomonacidal drugs. 6. 2,4-Dichloro derivatives of piperidino- and piperazinyl-1,3,5-triazine].

The nucleophilic substitution of one chlorine atom in cyanuric chloride (1) by piperidine derivatives (2a-c) leads to the 6-substituted 2,4-dichloro-1,3,5-triazines (3a-c). Reaction of 1 with piperazine derivatives (4a-c) yields the substituted 2,4-dichloro-6-(1-piperazinyl)-1,3,5-triazines (5a-c). Structures of type 3 and 5 may be characterized by the spectroscopic data. In the mass spectra, the degradation of 3c leading to the base peak comprises the cleavage into a 2,4-dichlorotriazinyl radical and a 3,4-dihydroquinolinium ion m/e 132. Strong activity is exhibited by 5a and 5b towards Trichomonas vaginalis. Moreover, 5a displays strong antimycotic activity towards Trichophyton mentagrophytes, Trichophyton rubrum, and Microsporum canis. Additionally, 5a and 5b are capable of exerting very strong anthelminthic activity towards Caenorhabditis elegans.