N-substituted perhydrodiazine

An N-substituted perhydro-3,4-diazine of formula

• in which
• Z is O;
• RA is hydroxyl, CO2R1, halogen, cyano, C(O)NR12, OR2, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, COR1, S(O)nR1where n=0, 1 or 2, or C(O)SR1;
• R is CO2H, CHO, CN, C(O)OR3, C(S)OR3, C(O)SR3, C(S)SR3, C(O)NR4R5, C(S)NR4R5, C(O)NHCO2R6, C(O)NHSO2R6, C(O)NHSO3R6, C(O)R2, P(O)R1OR1, P(O)(OR1)2, S(O)nR2 where n=0, 1, or 2 or SO2NHR1;
• m has the value 0, 1, 2 or 3
• and in which the variables R1 to R7 are as defined below:
• R1 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C3-alkoxy-C1-C3-alkyl, C3-C6-alkenyl or C3-C6-alkynyl;
• R2 is C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, hydroxycarbonyl-C1-C6-alkyl, C1-C6-alkoxycarbonyl-C1-C6-alkyl, C1-C6-alkylthio-C1-C6-alkyl, C1-C6-alkylsulfinyl-C1-C6-alkyl, C1-C6-alkylsulfonyl-C1-C6-alkyl, C3-C6-cycloalkyl-C1-C6-alkyl, C3-C6-alkenyloxycarbonyl-C1-C6-alkyl, C3-C6-alkynyloxycarbonyl-C1-C6-alkyl, C3-C6-cycloalkoxy-C1-C6-alkyl, C3-C6-alkenyloxy-C1-C6-alkyl, C3-C6-alkynyloxy-C1-C6-alkyl, C1-C6-haloalkoxy-C1-C6-alkyl, C3-C6-haloalkenyloxy-C1-C6-alkyl, C3-C6-haloalkynyloxy-C1-C6-alkyl, C3-C6-cycloalkyl-C1-C6-thioalkyl, C3-C6-alkenylthio-C1-C6-alkyl, C3-C6-alkynylthio-C1-C6-alkyl, cyano-C1-C6-alkyl, C3-C6-halocycloalkyl-C1-C6-alkyl, halo-C2-C6-alkenyl, C1-C6-alkoxy-C3-C6-alkenyl, C1-C6-haloalkoxy-C3-C6-alkenyl, C1-C6-alkylthio-C3-C6-alkenyl, C3-C6-haloalkynyl, C1-C6-alkoxy-C3-C6-alkynyl, C1-C6-haloalkoxy-C3-C6-alkynyl, C1-C6-alkylthio-C3-C6-alkynyl, C1-C6-alkylcarbonyl, CHR1COR7, CHR1P(O)(OR7)2, P(O)(OR7)2, CHR1P(S)(OR7)2, CHR1C(O)NR4R5, CHR1C(O)NH2, or
• R2 is phenyl, pyridyl, benzyl, phenoxy-C1-C6-alkyl, benzyloxy-C1-C6-alkyl, where the phenyl or pyridyl groups of the five last-mentioned substituents may be substituted by halogen, C1-C4-alkyl, C1-C4-alkoxy or C1-C4-haloalkyl,
• R3 is C1-C15-alkyl, C3-C8-cycloalkyl, C2-C10-alkenyl, C3-C10-alkynyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkylthio-C1-C6-alkyl, C1-C6-alkylsulfinyl-C1-C6-alkyl, C1-C6-alkylsulfonyl-C1-C6-alkyl, C1-C3-alkoxy-C1-C3-alkoxy-C1-C3-alkyl, C3-C6-cycloalkyl-C1-C6-alkyl, carboxyl-C1-C6-alkyl, C1-C6-alkoxycarbonyl-C1-C6-alkyl, C1-C6-alkoxycarbonyl-C2-C6-alkenyl, C3-C6-alkenyloxycarbonyl-C1-C6-alkyl, C3-C6-alkynyloxycarbonyl-C1-C6-alkyl, C3-C8-cycloalkoxy-C1-C6-alkyl, C3-C6-alkenyloxy-C1-C6-alkyl, C3-C6-alkynyloxy-C1-C6-alkyl, C1-C6-haloalkoxy-C1-C6-alkyl, C3-C6-haloalkenyloxy-C1-C6-alkyl, C3-C6-haloalkynyloxy-C1-C6-alkyl, C3-C6-cycloalkyl-C1-C6-thioalkyl, C3-C6-alkenylthio-C1-C6-alkyl, C3-C6-alkynylthio-C1-C6-alkyl, cyano-C1-C6-alkyl, C3-C6-halocycloalkyl-C1-C6-alkyl, halo-C3-C6-alkenyl, C1-C6-alkoxy-C3-C6-alkenyl, C1-C6-haloalkoxy-C3-C6-alkenyl, C1-C6-alkylthio-C3-C6-alkenyl, C3-C6-haloalkynyl, C1-C6-alkoxy-C3-C6-alkynyl, C1-C6-haloalkoxy-C3-C6-alkynyl, C1-C6-alkylthio-C3-C6-alkynyl, or
• R3 is CHR1COR7, CHR1P(O)(OR7)2, P(O)(OR7)2, CHR1P(S)(OR7)2, CHR1C(O)NR4R5, CHR1C(O)NH2, phenoxy-C1-C6-alkyl, benzyloxy-C1-C6-alkyl, where the phenyl groups of the two last-mentioned substituents may be substituted by halogen, C1-C4-alkyl, C1-C4-alkoxy or C1-C4-haloalkyl;
• or
• R3 is phenyl, pyridyl, naphthyl, quinolyl, quinazolyl, quinoxalyl, 1-methylindolyl, 1-methylbenzimidazolyl, 2-methylindazolyl, benzofuranyl, benzothienyl, benzoxazolyl, benzothiazolyl, benzyl, where the 14 last-mentioned substituents may carry, in adjacent positions, a divalent substituent selected from the group consisting of methylenedioxy, difluoromethylenedioxy, chlorofluoromethylenedioxy and dichloromethylenedioxy, or may in each case be mono- to pentasubstituted by halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, amino, C1-C4-monoalkylamino, C1-C4-dialkylamino, C3-C6-cycloalkyl, C1-C4-alkoxycarbonyl, C1-C4-alkoxycarbonyl-C1-C4-alkyl, hydroxyl, nitro or cyano;
• R4 is hydrogen, C1-C6-alkyl or C1-C6-alkoxy;
• R5, R6 independently of one another are hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxycarbonyl-C1-C6-alkyl, C1-C6-alkoxycarbonyl-C2-C6-alkenyl, where the alkenyl chain may additionally carry one to three halogen and/or cyano radicals, benzyl which, in adjacent positions of the phenyl ring, may carry a divalent substituent selected from the group consisting of methylenedioxy, difluoromethylenedioxy, chlorofluoromethylenedioxy and dichloromethylenedioxy, or which may be mono- to pentasubstituted by halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, C3-C6-cycloalkyl, C1-C4-alkoxycarbonyl, C1-C4-alkoxycarbonyl-C1-C4-alkyl, hydroxyl, nitro or cyano, or
• R4 and R5 together with the nitrogen atom to which they are attached are a saturated or unsaturated 4- to 7-membered azaheterocycle which, in addition to carbon ring members, optionally has one of the following members:
• —O—, —S—, —N═, —NH— or —N(C1-C6-alkyl)—;
• R7 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C3-alkoxy-C1-C3-alkyl, C2-C6-cyanoalkyl, C3-C6-alkenyl or C3-C6-alkynyl.