Reaction Steps
As representative compounds having the above formula, A in the formula represents an oxygen atom or =NR1 radical in which R1 is a hydroxyl radical or an amino radical which may substituted and especially when A is =NR1, R1 in =C=N-R1 formed as the result of dehydrating reaction between a carbonyl reagent having the formula of H2N-R1 and a ketone radical is representative. As representative compounds of H2N-R1, there can be mentioned, for example, hydroxylamine, hydrazine, semicarbazide, thiosemicarbazide and the like. As exemplified hydrazines there can be mentioned hydrazine, phenylhydrazine or phenylhydrazine substituted with an aryl, alkoxyl, carboalkoxyl radical or halogen atom, and isonicotinicacid hydrazide. Also as semicarbazides, there can be mentioned phenylsemicarbazide, or phenylsemicarbazide substituted with an alkyl, alkoxyl, carboalkoxyl radical or halogen atom. As thiosemicarbazide, there can be mentioned several derivatives like those in semicarbazides. Also, as Z in the above formula, Z represents a 5-, 6- or 7- membered alicyclic ring or heterocyclic ring containing nitrogen, oxygen or sulfur atom both of which rings may be saturated, unsaturated or substituted and as exemplified examples of Z, for example, cyclopentanone, cyclohexanone, cyclohexadione, cyclohexenone piperidone (for example, 2-, 3-, 4- piperidone), lactone (for example, 4-~7-membered ring), pyrrolidone, hydantoin and the like are representative. These alicyclic and heterocyclic ring may contain more than one substituent such as alkyl, aryl, alkoxyl, aryloxy, acyl alkoxycarbonyl radicals, or halogen, nitrile, nitro, sulfonamido or acylamino or may form a condensed ring at suitable place (for example, indanone, benzocyclohexenone, benzocycloheptenone, oxyindole). Also, these alicyclic or heterocyclic rings may contain more than one --S-Y radical (wherein Y has the same meaning as above) at the carbon atom next the carbonyl radical. X in the formula represents halogen atoms such as fluorine, chlorine and bromine and --O-W wherein W is preferred to be an alkyl radical having 1~5 carbon atoms or aryl or a heterocyclic ring such as substituted or unsubstituted benzene, pyridine, furan, or thiophene. When W is an acyl radical, that is, --COR3, R3 is preferred to be an aryl or alkyl radical. When W is --SO2 -R2, -R2 is preferred to be an alkyl, aryl radical and further heterocyclic rings such as pyridine, furan, thiophene, piperidine, pyrrolidone, and morpholine. Also, X may be ##STR5## wherein as the representative heterocyclic ring containing nitrogen formed with V, there can be mentioned succinimide, phthalimide, hydantoin, urazol and their derivatives. On the other hand, Y in the formula is a radical forming a compound having development inhibiting action such as an allylmercapto compound, mercapto heterocyclic compound, thioglycollicacid type compound, cysteine or glutathione with sulphur atom when the thioether bond is split and the sulfur atom is detached. As representative mercapto compounds of Y, there can be mentioned heterocyclic mercapto compounds such as mercaptotetrazole type compound, especially 1-phenyl-2-mercaptotetrazole, 1-nitrophenyl-5-mercaptotetrazole, 1-naphthyl-5-mercaptotetrazole, mercaptothiazole compounds, especially 2-mercaptobenzthiazole, mercaptonaphthothiazole, or mercapto-oxadiazole compounds, mercaptopiperidine compounds, mercaptothiadiazole compounds, especially 2-mercaptothiadiazolotriazine or mercaptotriazine compounds, mercaptotriazole compounds, mercaptobenzene compounds, especially 1-mercapto-2-benzoic acid, 1-mercapto-2-nitrobenzene, 1-mercapto-3-heptadecanoylaminbenzene. As exemplified examples of the compounds having the above formula, there can be mentioned the following compounds: ##STR6##
