Difluoromethyltriazolone compounds, use of the same and intermediates for the production thereof

A difluoroacetyl semicarbazide compound of the formula [XXVI]:

• 42
• wherein,
• R1 represents A1-L1-, A1-ON═CA2-, A1-ON═C(Me)CH2ON═CA2-, A1-C(A2)=N—OCH2—, A1S—C(A2)=N—, A1-C(═S)NH—, A1S—C(═S)NH—, A1S—C(SA2)=N—, A1-ON═C(CN)—, A1-ON═C(Me)CH2ON═C(CN)—, A1-C(CN)═N—OCH2—, halogen atom, nitro or cyano;
• wherein L1 represents single bond, oxygen atom, sulfur atom, carbonyl, —OCH2—, —SCH2—, —C(═O)O—, —OC(═O)—, —C(═O)OCH2—, —NH— or C1-C6 alkylimino;
• A1 and A2, which are the same or different, represent hydrogen atom, C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C3-C10 cycloalkyl, (C3-C10 cycloalkyl) alkyl, C5-C10 cycloalkenyl, (C5-C10 cycloalkenyl) alkyl, phenyl, naphthyl, phenyl C1-C10 alkyl, naphtyl C1-C10 alkyl, 5- or 6-membered heterocyclic group optionally condensed with a benzene ring, or methyl substituted by a 5- or 6-membered heterocyclic group optionally condensed with a benzene ring;
• the alkyl, the alkenyl, the alkynyl, the cycloalkyl, the cycloalkylalkyl, the cycloalkenyl and the cycloalkenyl alkyl represented by A1 and A2, may optionally be each substituted by one or more substituents selected from the group consisting of halogen atom(s), cyano, nitro, C1-C10 alkoxy, C1-C10 haloalkoxy, C1-C10 alkylthio, C1-C10 haloalkylthio, (C1-C9 alkyl) carbonyl, (C1-C9 alkoxy) carbonyl, (C1-C9 alkyl) carbonylamino, phenyl, phenoxy, benzyloxy and tri (C1-C10 alkyl) silyl;
• the phenyl, the naphthyl, the benzene ring in the phenylalkyl, the naphthalene ring in the phenylnaphthyl, the heterocyclic group, and the heterocyclic ring in the methyl substituted by a heterocylic group, represented by A1 and A2, may optionally be each substituted by one or more substituents selected from the group consisting of halogen atoms, cyano, nitro, C1-C10 alkyl, C1-C10 haloalkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 haloalkoxy, C1-C10 alkylthio, C1-C10 haloalkylthio, (C1-C9 alkyl) carbonyl, (C1-C9 alkoxy) carbonyl, (C1-C9 alkyl) carbonylamino, phenyl, phenoxy, benzyloxy, tri(C1-C10 alkyl) silyl, methylenedioxy and difluoromethylenedioxy;
• with the proviso, when L1 is single bond, A1 is not a hydrogen atom;
• T represents optionally substituted m-phenylene, optionally substituted m-azaphenylene or optionally substituted m-diazaphenylene bonded to R1 and to CH2 each via a carbon atom;
• wherein the substituent(s) are one or more substituents selected from the group consisting of halogen atom(s), cyano, nitro, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio and (C1-C5 alkoxy) carbonyl.

A semicarbazide compound of the formula [VII]:

• 43
• wherein;
• R1 represents A1-L1-, A1-ON═CA2-, A1-ON═C(Me)CH2ON═CA2-, A1-C(A2)=N—OCH2—, A1S—C(A2)=N—, A1-C(═S)NH—, A1S—C(═S)NH—, A1S—C(SA2)=N—, A1-ON═C(CN)—, A1-ON═C(Me)CH2ON═C(CN)—, A1-C(CN)═N—OCH2—, halogen atom, nitro or cyano;
• wherein, L1 represents single bond, oxygen atom, sulfur atom, carbonyl, —OCH2—, —SCH2—, —C(═O)O—, —OC(═O)—, —C(═O)OCH2—, —NH— or C1-C6 alkylimino;
• A1 and A2, which are the same or different, represent hydrogen atom, C1-C10 alkyl, C2-C10 alkenyl, C2-C10 alkynyl, C3-C10 cycloalkyl, (C3-C10 cycloalkyl) alkyl, C5-C10 cycloalkenyl, (C5-C10 cycloalkenyl) alkyl, phenyl, naphthyl, phenyl C1-C10 alkyl, naphtyl C1-C10 alkyl, 5- or 6-membered heterocyclic group optionally condensed with a benzene ring, or methyl substituted by a 5- or 6-membered heterocyclic group optionally condensed with a benzene ring;
• the alkyl, the alkenyl, the alkynyl, the cycloalkyl, the cycloalkylalkyl, the cycloalkenyl and the cycloalkenylalkyl, represented by A1 and A2, may optionally be each substituted by one or more substituents selected from the group consisting of halogen atom(s), cyano, nitro, C1-C10 alkoxy, C1-C10 haloalkoxy, C1-C10 alkylthio, C1-C10 haloalkylthio, (C1-C9 alkyl) carbonyl, (C1-C9 alkoxy) carbonyl, (C1-C9 alkyl) carbonylamino, phenyl, phenoxy, benzyloxy and tri(C1-C10 alkyl) silyl;
• the phenyl, the naphthyl, the benzene ring in the phenylalkyl, the naphthalene ring in the phenylnaphthyl, the heterocyclic group, and the heterocyclic ring in the methyl substituted by a heterocylic group, represented by A1 and A2, may optionally be each substituted by one or more substituents selected from the group consisting of halogen atom(s), cyano, nitro, C1-C10 alkyl, C1-C10 haloalkyl C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 haloalkoxy, C1-C10 alkylthio, C1-C10 haloalkylthio, (C1-C9 alkyl) carbonyl, (C1-C9 alkoxy) carbonyl, (C1-C9 alkyl) carbonylamino, phenyl, phenoxy, benzyloxy, tri(C1-C10 alkyl) silyl, methylenedioxy and difluoromethylenedioxy;
• with the proviso, when L1 is single bond, A1 is not a hydrogen atom;
• T represents optionally substituted m-phenylene, optionally substituted m-azaphenylene or optionally substituted m-diazaphenylene bonded to R1 and to CH2 each via a carbon atom;
• wherein the substituent(s) are one or more substituents selected from the group consisting of halogen atom(s), cyano, nitro, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio and (C1-C5 alkoxy) carbonyl.