Patent ID: 6518296
Filing Date: 2003-02-11
Classification: C07D

Abstract:
A substituted 3-thiocarbamoylpyrazole of the formula (I): whereinR1 represents H2Nâ€”CSâ€”, m represents the number 0 or 1, n represents the number 0,1 or 2, R2 represents cyano-(C1-C4)-alkyl, thiocyanato-(C1-C4)-alkyl, nitro-(C1-C4)-alkyl, (C1-C6)-alkylthio-(C1-C4)-alkyl, (C1-C6)-alkylsulphinyl-(C1-C4)-alkyl, (C1-C6)-alkylsulphonyl-(C1-C4)-alkyl, (C1-C4)-halogenoalkylthio-(C1-C4)-alkyl having 1 to 6 halogen atoms, (C1-C4)-halogenoalkylsulphinyl-(C1-C4)-alkyl having 1 to 6 halogen atoms, (C1-C4)-halogenoalkylsulphonyl-(C1-C4)-alkyl having 1 to 6 halogen atoms, (C2-C6)-alkenylthio-(C1-C4)-alkyl, (C2-C6)-alkenylsulphinyl-(C1-C4)-alkyl, (C2-C6)-alkenylsulphonyl-(C1-C4)-alkyl, (C2-C6)-alkynylthio-(C1-C4)-alkyl, (C2-C6)-alkynylsulphinyl-(C1-C4)-alkyl, (C2-C6)-alkynylsulphonyl-(C1-C4)-alkyl, (C1-C4)-alkoxy-carbonyl-(C1-C4)-alkyl, (C1-C4)-halogenoalkoxy-carbonyl-(C1-C4)-alkyl having 1 to 5 halogen atoms, (C1-C6)-alkoxy-carbonyl, (C1-C6)-alkyl-carbonyl, (C1-C6)-alkoxy-(C1-C4)-alkyl, (C1-C6)-halogenoalkoxy-(C1-C4)-alkyl having 1 to 6 halogen atoms, (C1-C4)-alkoxy-(C1-4)-alkylthio-(C1-C4)-alkyl, (C1-C4)-alkoxy-(C1-C4)-alkylsulphinyl-(C1-C4)-alkyl, alkoxy-(C1-C4)-alkylsulphonyl-(C1-C4)-alkyl, (C1-C4)-halogenoalkoxy-(C1-C4)-alkylthio-(C1-C4)-alkyl having 1 to 5 halogen atoms, (C1-C4)-halogenoalkoxy-(C1-C4)-alkylsulphinyl-(C1-C4)-alkyl having 1 to 5 halogen atoms, (C1-C4)-halogenoalkoxy-(C1-C4)-alkylsulphonyl-(C1-C4)-alkyl having 1 to 5 halogen atoms, (C1-C4)-alkylamino-(C1-C4)-alkyl, di-(C1-4)-alkylamino-(C1-G4)-alkyl, tri-(C1-C4)-alkylsilyl-(C1-C4)-alkyl; or represents (C5-C6)-cycloalkenyl or (C3-C6)-cycloalkyl-(C1-C2)-alkyl, which is optionally mono- to pentasubstituted by substituents selected from the group consisting of (C1-C4)-alkyl, (C1-C4)-alkoxy, halogen, (C1-C4)-halogenoalkyl having 1 to 5 halogen atoms and (C1-C4)-halogenoalkoxy having 1 to 5 halogen atoms; or represents phenyl, phenyl-(C1-C2)-alkyl, phenoxy-(C1-C2)alkyl, phenylthio-(C1-C2)-alkyl, phenylsulphinyl-(C1-C2)-alkyl, phenylsulphonyl-(C1-C2)-alkyl, phenyl-(C1-C2)-alkyloxy-(C1-C2)-alkyl, phenyl-(C1-C2)-alkylthio-(C1-C2)-alkyl, phenyl-(C1-C2)-alkylsulphinyl-(C1-C2)-alkyl, phenyl-(C1-C2)-alkylsulphonyl-(C1-C2)-alkyl, the phenyl moiety of which is optionally mono- to trisubstituted by substituents selected from the group consisting of halogen, (C1-C6)-alkyl, (C2-C6)-alkenyl, (C1-C6)-alkoxy, (C2-C6)alkenyloxy, (C1-C4)-alkylthio, (C1-C4)-alkylsulphinyl, (C1-C4)-alkylsulphonyl; (C1-C6)-halogenoalkyl, (C2-C4)-halogenoalkenyl, (C1-C4)-halogenoalkoxy, (C1-4)-halogenoalkylthio, (C1-C4)-halogenoalkylsulphinyl and (C1-C4)-halogenoalkylsulphonyl having 1 to 5 halogen atoms; cyano, nitro, hydroxyl, hydrazino, (C1-C6)-dialkylhydrazino, amino, (C1-C6)-alkylamino, di-(C1-C6)-alkylamino, (C1-C6)-alkylimino, (C1-C4)-alkyl-carbonyl, (C1-C4)-alkyl-carbonyloxy, phenyl or phenoxy, which is optionally mono- to trisubstituted by substituents selected from the group consisting of halogen, (C1-C4)-alkyl, (C1-C4)-halogenoalkyl having 1 to 5 halogen atoms, (C1-C4)-alkoxy and (C1-C4)-halogenoalkoxy and (C1-C4)-halogenoalkylthio having 1 to 5 Halogen atoms, SF5 or the grouping whereinRâ€² and Râ€³ independently represent hydrogen or (C1-C6)-alkyl and Z represents â€”CO or â€”SO2, R2 where m=0, represents thiocyanato, chlorine, bromine, iodine, nitro, cyano, hydroxyl, chlorosulphonyl, (C1-C4)-alkoxy, (C2-C4)-alkenyloxy; (C1-C4)-halogenoalkyl, (C2-C4)-halogenoalkenyl, (C1-C4)-halogenoalkoxy and (C2-C4)-halogenoalkenyloxy having 1 to 5 halogen atoms; (C1-C4)-alkyl-carbonyloxy, formyl, tri-(C1-C4)-alkylsilylethinyl or represents phenoxy which is optionally mono- to pentasubstituted by the phenyl substituents mentioned above for R2, or represents one of the following groupings: â€”NHR4, â€”NR4R5, â€”NHNH2, â€”CONH2, â€”CSNH2, â€”CONR4R5, â€”SO2NR4R5, â€”CR6&boxH;NOR7, â€”CH(OH)R8 or â€”CH(CN)OR9,whereinR4 and R5 independently represent hydrogen, cyano, (C1-C4)-alkyl or represent phenyl or benzyl, which is optionally mono- to pentasubstituted by the phenyl substituents mentioned above for R2, R6 represents hydrogen or (C1-C4)-alkyl, R7 represents hydrogen, (C1-C4)-alkyl or benzyl, which is optionally mono- to pentasubstituted by the phenyl substituents mentioned above for R2, R8 represents (C1-C4)-alkyl or (C1-C4)-halogenoalkyl having 1 to 5 halogen atoms, R9 represents (C1-C4)-alkyl, R3 represents hydrogen, amino, chlorine, bromine, iodine or represents one of the following groupings: â€”NHâ€”COâ€”R10, â€”NHR11, â€”OR12, â€”SR12 or â€”NR13â€”CXâ€”C(R14, R15, R16), whereinR10 represents (C1-C4)-alkyl, (C1-C4)-halogenoalkyl having 1 to 5 halogen atoms, (C1-C4)-alkoxy-(C1-C4)-alkyl or represents phenyl or phenoxy, which is optionally mono- to pentasubstituted by the phenyl substituents mentioned above for R2, R11 represents (C1-C4)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, formyl, (C1-C4)-alkyl-carbonyl, (C1-C4)-halogenoalkyl-carbonyl having 1 to 5 halogen atoms or (C1-C4)-alkoxy-carbonyl, R12 represents (C1-C4)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, di-(C1-C4)-alkylamino-(C1-C4)-alkyl; phenyl-(C1-C2)-alkyl which is optionally mono- to pentasubstituted by the phenyl substituents mentioned above for R2; or represents the grouping â€”P(&boxH;Y)(OR17)(SR18),whereinR17 and R18 independently represent (C1-C4)-alkyl and Y represents oxygen or sulfur, R13 represents hydrogen, (C1-C4)-alkyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, propargyl, allyl, (C1-C4)-alkoxy-carbonyl, (C1-C4)-alkyl-carbonyl; or represents benzyl which is optionally mono- to pentasubstituted by the phenyl substituents mentioned above for R2, or represents the grouping â€”COâ€”C(R14, R15, R16),R14 represents hydrogen, (C1-C4)-alkyl, halogen, (C1-C4)-halogenoalkyl having 1 to 5 halogen atoms or represents phenyl which is optionally mono- to pentasubstituted by the phenyl substituents mentioned above for R2, R15 represents hydrogen, (C1-C4)-alkyl, halogen, (C1-4)-halogenoalkyl and (C1-C4)-halogenoalkoxy-(C1-C4)-alkyl having 1 to 5 halogen atoms, (C1-C4)-alkylthio-(C1-C4)-alkyl, (C1-C4)-alkylsulphinyl-(C1-C4)-alkyl, (C1-C4)-alkylsulphonyl-(C1-C4)-alkyl, (C1-C4)-alkoxy-[(C1-C4)-alkoxy]r(C1-C4)-alkyl where r=0 to 2, hydroxyl, (C1-C4)-alkoxy-carbonyl-(C1-C4)-alkyl and (C1-C4)-alkoxy, R16 represents hydroxyl, (C1-C4)-alkoxy, (C1-C4)-halogenoalkoxy having 1 to 5 halogen atoms or (C1-C4)-alkoxy-[(C1-C4)-alkoxy]q wherein q=1 or 2, X represents oxygen or sulfur and Ar represents phenyl which is optionally mono- to trisubstituted by the phenyl substituents mentioned above for R2.