Abstract
The present invention relates to Bis(hetero)aryl thioether (thio)amides derivatives and the uses thereof for controlling phytopathogenic microorganisms such as phytopathogenic fungi. It also relates to processes and intermediates for preparing these compounds.
Claims
1. Compounds of formula (I-A) ##STR00266## wherein T is O or S, n is 0 or 1, m is 0, 1 or 2, R.sup.1 is hydrogen, hydroxyl, cyano, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy, C(O)R.sup.10, C(O)(OR.sup.11), S(O)R.sup.12, S(O).sub.2R.sup.12, C(O)N(R.sup.13).sub.2 or S(O).sub.2N(R.sup.14).sub.2, wherein R.sup.10, R.sup.11 and R.sup.12 are independently C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.3-C.sub.8-cycloalkyl or C.sub.2-C.sub.6-alkenyl, R.sup.13 and R.sup.14 are independently hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.3-C.sub.8-cycloalkyl or C.sub.2-C.sub.6-alkenyl, R.sup.2 and R.sup.3 are independently hydrogen, halogen, cyano, hydroxyl, carboxyl, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-alkoxycarbonyl or C.sub.3-C.sub.8-cycloalkyl, or R.sup.2 and R.sup.3 form together with the carbon atom to which they are attached to a C.sub.3-C.sub.8-cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring, R.sup.4 and R.sup.5 are independently hydrogen, halogen, cyano, hydroxyl, carboxyl, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-alkoxycarbonyl or C.sub.3-C.sub.8-cycloalkyl, or R.sup.4 and R.sup.5 form together with the carbon atom to which they are attached to a C.sub.3-C.sub.8-cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring, or R.sup.2 and R.sup.4 form together with the carbon atom to which they are attached to a C.sub.3-C.sub.8-cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring, and R.sup.3 and R.sup.5 are independently hydrogen or halogen, or R.sup.2 and R.sup.4 form together a group of formula **C(R.sup.3)C(R.sup.5).sup.##, wherein ** is the point of attachment to N(R.sup.1), .sup.## is the point of attachment to R.sup.6, and R.sup.3 and R.sup.5 are independently hydrogen, halogen or C.sub.1-C.sub.6-alkyl, R.sup.6 is C.sub.3-C.sub.12-carbocyclyl, C.sub.6-C.sub.14-aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C.sub.3-C.sub.12-carbocyclyloxy, C.sub.6-C.sub.14-aryloxy, 5- to 14-membered heteroaryloxy, 3- to 14-membered heterocyclyloxy, C.sub.1-C.sub.3-alkoxy or C.sub.1-C.sub.3-haloalkoxy, wherein C.sub.1-C.sub.3-alkoxy and C.sub.1-C.sub.3-haloalkoxy are independently substituted with one substituent selected from the group consisting of C.sub.3-C.sub.12-carbocyclyl, C.sub.6-C.sub.14-aryl, 3- to 14-membered heterocyclyl and 5- to 14-membered heteroaryl, wherein said C.sub.3-C.sub.12-carbocyclyl, C.sub.6-C.sub.14-aryl, 3- to 14-membered heterocyclyl and 5- to 14-membered heteroaryl in turn are optionally substituted with one to four substituents R.sup.6S, wherein C.sub.3-C.sub.12-carbocyclyl, C.sub.6-C.sub.14-aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C.sub.3-C.sub.12-carbocyclyloxy, C.sub.6-C.sub.14-aryloxy, 5- to 14-membered heteroaryloxy and 3- to 14-membered heterocyclyloxy are optionally substituted with one to four substituents R.sup.6S, wherein R.sup.6S is independently halogen, cyano, isocyano, nitro, hydroxyl, oxo, mercapto, pentafluorosulfanyl, oxo, methylidene, halomethylidene, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.2-C.sub.6-haloalkynyl, C.sub.2-C.sub.6-alkenyloxy, C.sub.2-C.sub.6-haloalkenyloxy, C.sub.1-C.sub.6-alkylsulfanyl, C.sub.1-C.sub.6-haloalkylsulfanyl, C.sub.3-C.sub.8-cycloalkylsulfanyl, C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-haloalkylsulfinyl, C.sub.3-C.sub.8-cycloalkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylsulfonyl, C.sub.3-C.sub.8-cycloalkylsulfonyl, C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-cycloalkoxy, C.sub.3-C.sub.8-cycloalkenyl, C.sub.6-C.sub.14-aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, N(R.sup.15).sub.2, C(O)R.sup.16, C(O)(OR.sup.17), C(O)N(R.sup.18).sub.2, S(O).sub.2N(R.sup.19).sub.2, OSi(C.sub.1-C.sub.6-alkyl).sub.3 or Si(C.sub.1-C.sub.6-alkyl).sub.3, wherein said C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.2-C.sub.6-haloalkynyl, C.sub.2-C.sub.6-alkenyloxy, C.sub.2-C.sub.6-haloalkenyloxy, C.sub.1-C.sub.6-alkylsulfanyl, C.sub.1-C.sub.6-haloalkylsulfanyl, C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-haloalkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylsulfonyl, OSi(C.sub.1-C.sub.6-alkyl).sub.3 and Si(C.sub.1-C.sub.6-alkyl).sub.3 are furthermore optionally substituted with one to three substituents independently selected from the group consisting of cyano, hydroxyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, OSi(C.sub.1-C.sub.6-alkyl).sub.3, Si(C.sub.1-C.sub.6-alkyl).sub.3, C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-halocycloalkyl and 3- to 7-membered heterocyclyl, and wherein said C.sub.3-C.sub.8-cycloalkylsulfanyl, C.sub.3-C.sub.8-cycloalkylsulfinyl, C.sub.3-C.sub.8-cycloalkylsulfonyl, C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-cycloalkoxy, C.sub.3-C.sub.8-cycloalkenyl, C.sub.6-C.sub.14-aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl are furthermore optionally substituted with one to four substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkoxycarbonyl, C.sub.1-C.sub.6-haloalkoxycarbonyl, C.sub.2-C.sub.6-alkenyl, C.sub.3-C.sub.8-cycloalkyl and C.sub.3-C.sub.8-halocycloalkyl, or two substituents C.sub.1-C.sub.6-alkyl attached to the same carbon atom form a C.sub.3-C.sub.8-cycloalkyl-ring, or two R.sup.6S substituents optionally form together with the carbon atom to which they are attached to a C.sub.3-C.sub.8-cycloalkyl-ring, and wherein R.sup.15 is independently hydrogen, C.sub.1-C.sub.6-alkyl or C.sub.3-C.sub.8-cycloalkyl, wherein said C.sub.1-C.sub.6-alkyl is furthermore optionally substituted with one to three substituents independently selected from the group consisting of cyano, hydroxyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, OSi(C.sub.1-C.sub.6-alkyl).sub.3, Si(C.sub.1-C.sub.6-alkyl).sub.3, C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-halocycloalkyl and 3- to 7-membered heterocyclyl, and wherein said C.sub.3-C.sub.8-cycloalkyl is furthermore optionally substituted with one to four substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkoxycarbonyl, C.sub.1-C.sub.6-haloalkoxycarbonyl, C.sub.2-C.sub.6-alkenyl, C.sub.3-C.sub.8-cycloalkyl and C.sub.3-C.sub.8-halocycloalkyl, R.sup.16, R.sup.17, R.sup.18 and R.sup.19 are independently hydrogen, C.sub.1-C.sub.6-alkyl or C.sub.1-C.sub.6-haloalkyl, wherein said C.sub.1-C.sub.6-alkyl or C.sub.1-C.sub.6-haloalkyl are furthermore optionally substituted with one to three substituents independently selected from the group consisting of cyano, hydroxyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, OSi(C.sub.1-C.sub.6-alkyl).sub.3, Si(C.sub.1-C.sub.6-alkyl).sub.3, C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-halocycloalkyl and 3- to 7-membered heterocyclyl, the ring Y is a group of formula (II-a), (II-b), (II-c), (II-d), (II-e), (II-f), (II-g), (II-h), (II-i), (II-j), (II-k), (II-l), (II-m), (II-n), (II-o), (II-p), (II-q), (II-r), (II-s), (II-t), (II-u), (II-v), (II-w), (II-x), (II-y), (II-z), (II-aa), (II-ab) or (II-ac) ##STR00267## ##STR00268## ##STR00269## ##STR00270## ##STR00271## wherein * is the point of attachment to the group K-Q, # is the point of attachment to C(=T), A.sup.1 is CR.sup.8 or N, wherein R.sup.8 is hydrogen, halogen, cyano or C.sub.1-C.sub.4-alkyl, G is O, S or NR.sup.7L, wherein R.sup.7L is hydrogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl or C.sub.3-C.sub.8-cycloalkyl, q is 0, 1, 2, 3 or 4, x.sup.1 is 1 or 2, x.sup.2 is 0, 1 or 2, R.sup.7A, R.sup.7B, R.sup.7C, R.sup.7D, R.sup.7E, R.sup.7F and R.sup.7G are independently hydrogen, hydroxyl, halogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy or C.sub.3-C.sub.8-cycloalkyl R.sup.7H is hydrogen, C.sub.1-C.sub.4-alkyl or C.sub.1-C.sub.4-haloalkyl, R.sup.7K is methylidene, halomethylidene, halogen, hydroxyl, oxo, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.6-haloalkyl or C.sub.3-C.sub.6-cycloalkyl, or two substituents R.sup.7K form together with the carbon atoms to which they are attached to a C.sub.3-C.sub.8-cycloalkyl-ring, R.sup.7L is hydrogen, halogen, cyano, isocyano, hydroxyl, mercapto, nitro, amino, formyl, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-hydroxyalkyl, C.sub.1-C.sub.6-alkylcarbonyl, C.sub.1-C.sub.6-haloalkylcarbonyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.2-C.sub.6-haloalkynyl, C.sub.2-C.sub.6-alkenyloxy, C.sub.2-C.sub.6-haloalkenyloxy, C.sub.2-C.sub.6-alkynyloxy, C.sub.2-C.sub.6-haloalkynyloxy, C.sub.1-C.sub.6-alkylsulfanyl, C.sub.1-C.sub.6-haloalkylsulfanyl, C.sub.3-C.sub.8-cycloalkylsulfanyl, C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-haloalkylsulfinyl, C.sub.3-C.sub.8-cycloalkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylsulfonyl, C.sub.3-C.sub.8-cycloalkylsulfonyl, C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.6-cycloalkenyl, C.sub.6-C.sub.14-aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, C.sub.3-C.sub.8-cycloalkoxy, C.sub.6-C.sub.14-aryloxy, 5- or 6-membered heteroaryloxy, 3- to 7-membered heterocyclyloxy, OSi(C.sub.1-C.sub.6-alkyl).sub.3, Si(C.sub.1-C.sub.6-alkyl).sub.3, N(R.sup.20).sub.2, C(NR.sup.21)R.sup.22, NR.sup.23C(O)R.sup.24, C(O)(OR.sup.25), C(O)N(R.sup.26).sub.2, S(O).sub.2N(R.sup.27).sub.2 or S(O)(NR.sup.28)R.sup.29, wherein C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-hydroxyalkyl, C.sub.1-C.sub.6-alkylcarbonyl, C.sub.1-C.sub.6-haloalkylcarbonyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.2-C.sub.6-haloalkynyl, C.sub.2-C.sub.6-alkenyloxy, C.sub.2-C.sub.6-haloalkenyloxy, C.sub.2-C.sub.6-alkynyloxy, C.sub.2-C.sub.6-haloalkynyloxy, C.sub.1-C.sub.6-alkylsulfanyl, C.sub.1-C.sub.6-haloalkylsulfanyl, C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-haloalkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl and C.sub.1-C.sub.6-haloalkylsulfonyl are optionally substituted with one to three R.sup.7Sa substituents, wherein C.sub.3-C.sub.8-cycloalkylsulfanyl, C.sub.3-C.sub.8-cycloalkylsulfinyl, C.sub.3-C.sub.8-cycloalkylsulfonyl, C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.6-cycloalkenyl, C.sub.6-C.sub.14-aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, C.sub.3-C.sub.8-cycloalkoxy, C.sub.6-C.sub.14-aryloxy, 5- or 6-membered heteroaryloxy and 3- to 7-membered heterocyclyloxy are optionally substituted with one to three R.sup.7Sc substituents, and wherein R.sup.20 is independently hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.2-C.sub.6-haloalkynyl, C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-halo-cycloalkyl, C.sub.6-C.sub.14-aryl, 5- or 6-membered heteroaryl or 3- to 7-membered heterocyclyl, wherein C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl and C.sub.2-C.sub.6-haloalkynyl are optionally substituted with one to three substituents R.sup.7Sa, and wherein C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-halocycloalkyl, C.sub.6-C.sub.14-aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl are optionally substituted with one to three substitutents R.sup.7Sc, R.sup.21 and R.sup.22 are independently hydrogen, hydroxyl, amino, cyano, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, mono-(C.sub.1-C.sub.6-alkyl)amino or di-(C.sub.1-C.sub.6-alkyl)amino, wherein C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, mono-(C.sub.1-C.sub.6-alkyl)amino or di-(C.sub.1-C.sub.6-alkyl)amino are optionally substituted with one to three R.sup.7Sa substituents, R.sup.23, R.sup.24, R.sup.25, R.sup.26, R.sup.27, R.sup.28 and R.sup.29 are independently hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl and C.sub.3-C.sub.8-cycloalkyl, wherein C.sub.1-C.sub.6-alkyl and C.sub.1-C.sub.6-haloalkyl are optionally substituted with one to three R.sup.7Sa substituents, and wherein C.sub.3-C.sub.8-cycloalkyl is optionally substituted with one to three R.sup.7Sc substituents, wherein R.sup.7Sa is independently cyano, hydroxyl, carboxyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-halocycloalkyl, C.sub.1-C.sub.6-alkoxycarbonyl, OSi(C.sub.1-C.sub.6-alkyl).sub.3, Si(C.sub.1-C.sub.6-alkyl).sub.3, C.sub.6-C.sub.14-aryl or 3- to 7-membered heterocyclyl, R.sup.7Sc is independently halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, halomethylidene, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.2-C.sub.6-alkenyl, C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-halocycloalkyl, OSi(C.sub.1-C.sub.6-alkyl).sub.3 or 3- to 7-membered heterocyclyl, or two R.sup.7Sc substituents C.sub.1-C.sub.6-alkyl that are bound to the same carbon atom form together a C.sub.3-C.sub.8-cycloalkyl, R.sup.7M is hydrogen, halogen, cyano, isocyano, amino, nitro, hydroxyl, mercapto, carboxyl, C.sub.1-C.sub.6-alkoxycarbonyl, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-hydroxyalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.2-C.sub.6-haloalkynyl, C.sub.2-C.sub.6-alkenyloxy, C.sub.2-C.sub.6-haloalkenyloxy, C.sub.2-C.sub.6-alkynyloxy, C.sub.2-C.sub.6-haloalkynyloxy, C.sub.1-C.sub.6-alkylsulfanyl, C.sub.1-C.sub.6-haloalkylsulfanyl, C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-haloalkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylsulfonyl, C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-cycloalkenyl, C.sub.6-C.sub.14-aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C.sub.3-C.sub.8-cycloalkoxy, C.sub.6-C.sub.14-aryloxy, 3- to 14-membered heterocyclyloxy, 5- to 14-membered heteroaryloxy, OSi(C.sub.1-C.sub.6-alkyl).sub.3, Si(C.sub.1-C.sub.6-alkyl).sub.3, N(R.sup.30).sub.2, SR.sup.31, S(O)R.sup.31 or S(O).sub.2R.sup.31, wherein said C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-hydroxyalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.2-C.sub.6-haloalkynyl, C.sub.2-C.sub.6-alkenyloxy, C.sub.2-C.sub.6-haloalkenyloxy, C.sub.2-C.sub.6-alkynyloxy, C.sub.2-C.sub.6-haloalkynyloxy, C.sub.1-C.sub.6-alkylsulfanyl, C.sub.1-C.sub.6-haloalkylsulfanyl, C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-haloalkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylsulfonyl, OSi(C.sub.1-C.sub.6-alkyl).sub.3 and Si(C.sub.1-C.sub.6-alkyl).sub.3 are optionally substituted with one to three R.sup.8Sa substituents, said C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.6-cycloalkenyl, C.sub.6-C.sub.14-aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C.sub.3-C.sub.8-cycloalkoxy, C.sub.6-C.sub.14-aryloxy and 3- to 14-membered heterocyclyloxy and 5- to 14-membered heteroaryloxy are optionally substituted with one to three R.sup.8Sc substituents, and wherein R.sup.30 is independently hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.2-C.sub.6-haloalkynyl, C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-halo-cycloalkyl, C.sub.6-C.sub.14-aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclyl, wherein said C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl and C.sub.2-C.sub.6-haloalkynyl in turn are optionally substituted with one to three R.sup.8Sa substituents, said C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-halocycloalkyl, C.sub.6-C.sub.14-aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R.sup.8Sc substituents, R.sup.31 is C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.2-C.sub.6-haloalkynyl, C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-halocycloalkyl, C.sub.6-C.sub.14-aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclyl, wherein said C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl and C.sub.2-C.sub.6-haloalkynyl in turn are optionally substituted with one to three R.sup.8Sa substituents, said C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-halocycloalkyl, C.sub.6-C.sub.14-aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R.sup.8Sc substituents, and wherein R.sup.8Sa is independently selected from the group consisting of cyano, amino, nitro, hydroxyl, formyl, carboxyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-alkoxycarbonyl, C.sub.1-C.sub.6-haloalkoxycarbonyl, C.sub.1-C.sub.6-alkylcarbonyl, C.sub.1-C.sub.6-haloalkylcarbonyl, C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-halocycloalkyl, C.sub.1-C.sub.6-alkylsulfanyl, C.sub.1-C.sub.6-haloalkylsulfanyl, C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-haloalkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylsulfonyl, OSi(C.sub.1-C.sub.6-alkyl).sub.3, Si(C.sub.1-C.sub.6-alkyl).sub.3, 3- to 7-membered heterocyclyl and N(R.sup.32).sub.2, wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents independently selected from the group C.sub.1-C.sub.6-alkyl, R.sup.32 is independently hydrogen, formyl, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.3-C.sub.8-cycloalkyl or C.sub.1-C.sub.6-alkylcarbonyl, R.sup.8Sc is independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkoxycarbonyl, C.sub.1-C.sub.6-haloalkoxycarbonyl, C.sub.2-C.sub.6-alkenyl, C.sub.1-C.sub.6-alkylsulfanyl, C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-halocycloalkyl, OSi(C.sub.1-C.sub.6-alkyl).sub.3 and 3- to 7-membered heterocyclyl, wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents independently selected from the group C.sub.1-C.sub.6-alkyl, or two R.sup.8Sc substituents optionally form together with the carbon atom to which they are attached to a C.sub.3-C.sub.8-cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring, wherein said 3- to 7-membered heterocyclyl-ring in turn is optionally substituted with one to three substituents independently selected from the group C.sub.1-C.sub.6-alkyl, K is S(O).sub.p or S(O)NR.sup.4, wherein p is 0, 1 or 2, R.sup.4 is hydrogen or (C.sub.1-C.sub.6)-alkyl, Q is C.sub.6-C.sub.14-aryl, C.sub.3-C.sub.12-carbocyclyl, 3- to 14-membered heterocyclyl or 5- to 14-membered heteroaryl, wherein C.sub.6-C.sub.14-aryl, C.sub.3-C.sub.12-carbocyclyl, 3- to 14-membered heterocyclyl and 5- to 14-membered heteroaryl are optionally substituted with one to five substituents Q.sup.S wherein Q.sup.S is independently selected from the group consisting of halogen, cyano, isocyano, nitro, hydroxyl, mercapto, formyl, carboxyl, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkylcarbonyl, C.sub.1-C.sub.6-haloalkylcarbonyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxycarbonyl, C.sub.1-C.sub.6-haloalkoxycarbonyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.2-C.sub.6-haloalkynyl, C.sub.2-C.sub.6-alkenyloxy, C.sub.2-C.sub.6-haloalkenyloxy, C.sub.1-C.sub.6-alkylsulfanyl, C.sub.1-C.sub.6-haloalkylsulfanyl, C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-haloalkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylsulfonyl, C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-cycloalkoxy, C.sub.3-C.sub.6-cycloalkenyl, 3- to 7-membered heterocyclyl, 5- to 14-membered heteroaryl, OSi(C.sub.1-C.sub.6-alkyl).sub.3, Si(C.sub.1-C.sub.6-alkyl).sub.3, OC(O)R.sup.33, NR.sup.34C(O)R.sup.35, C(O)N(R.sup.36).sub.2, C(S)R.sup.37, C(S)N(R.sup.38).sub.2, C(NR.sup.39)R.sup.40, C(NOR.sup.41)R.sup.42 and N(R.sup.43).sub.2, wherein said C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkylcarbonyl, C.sub.1-C.sub.6-haloalkyl-carbonyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxycarbonyl, C.sub.1-C.sub.6-haloalkoxycarbonyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.2-C.sub.6-haloalkynyl, C.sub.2-C.sub.6-alkenyloxy, C.sub.2-C.sub.6-haloalkenyloxy, C.sub.1-C.sub.6-alkylsulfanyl, C.sub.1-C.sub.6-haloalkylsulfanyl, C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-haloalkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylsulfonyl, OSi(C.sub.1-C.sub.6-alkyl).sub.3 and Si(C.sub.1-C.sub.6-alkyl).sub.3 are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkoxycarbonyl, C.sub.1-C.sub.6-haloalkoxycarbonyl, C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-halocycloalkyl, Si(C.sub.1-C.sub.6-alkyl).sub.3 and 3- to 7-membered heterocyclyl, said C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-cycloalkoxy, C.sub.3-C.sub.6-cycloalkenyl, 3- to 7-membered heterocyclyl and 5- to 14-membered heteroaryl are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkoxycarbonyl, C.sub.1-C.sub.6-haloalkoxycarbonyl, C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-halocycloalkyl, C.sub.2-C.sub.6-alkenyl and 3- to 7-membered heterocyclyl, wherein said C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-halocycloalkyl and 3- to 7-membered heterocyclyl in turn are optionally substituted with two substituents forming together with the carbon atom to which they are attached to a C.sub.3-C.sub.8-cycloalkyl, R.sup.33, R.sup.34, R.sup.35, R.sup.36, R.sup.37, R.sup.38, R.sup.39, R.sup.40, R.sup.41 and R.sup.42 are independently hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl or C.sub.1-C.sub.6-alkoxy, wherein said C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl and C.sub.1-C.sub.6-alkoxy are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkoxycarbonyl, C.sub.1-C.sub.6-haloalkoxycarbonyl, C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-halocycloalkyl, Si(C.sub.1-C.sub.6-alkyl).sub.3 and 3- to 7-membered heterocyclyl, and wherein R.sup.43 is independently hydrogen, hydroxyl, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl or C.sub.3-C.sub.8-cycloalkyl, wherein said C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.2-C.sub.6-alkenyl and C.sub.2-C.sub.6-haloalkenyl are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkoxycarbonyl, C.sub.1-C.sub.6-haloalkoxycarbonyl, C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-halocycloalkyl, Si(C.sub.1-C.sub.6-alkyl).sub.3 and 3- to 7-membered heterocyclyl, wherein said C.sub.3-C.sub.8-cycloalkyl is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkoxycarbonyl, C.sub.1-C.sub.6-haloalkoxycarbonyl, C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-halocycloalkyl, C.sub.2-C.sub.6-alkenyl and 3- to 7-membered heterocyclyl, wherein said C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-halocycloalkyl and 3- to 7-membered heterocyclyl in turn are optionally substituted with two substituents forming together with the carbon atom to which they are attached to a C.sub.3-C.sub.8-cycloalkyl, as well as their N-oxides, salts, solvates and solvates of the salts and N-oxides thereof.
2. The compounds of formula (I-A) according to claim 1, wherein T is O or S, n is 0 or 1, m is 0, 1 or 2, R.sup.1 is hydrogen, hydroxyl, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy, C(O)R.sup.10 or C(O)(OR.sup.11), wherein R.sup.10 and R.sup.11 are independently C.sub.1-C.sub.4-alkyl, R.sup.2 and R.sup.3 are independently hydrogen, halogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-alkoxycarbonyl or C.sub.3-C.sub.6-cycloalkyl, or R.sup.2 and R.sup.3 form together with the carbon atom to which they are attached to a C.sub.3-C.sub.6-cycloalkyl-ring, R.sup.4 and R.sup.5 are independently hydrogen, halogen, C.sub.1-C.sub.4-alkyl or C.sub.1-C.sub.4-haloalkyl, or R.sup.4 and R.sup.5 form together with the carbon atom to which they are attached to a C.sub.3-C.sub.6-cycloalkyl-ring, or R.sup.2 and R.sup.4 form together with the carbon atom to which they are attached to a C.sub.3-C.sub.6-cycloalkyl-ring, and R.sup.3 and R.sup.5 are independently hydrogen, R.sup.6 is indanyl, tetrahydronaphthalenyl, spiro[cyclopropane-1,2-indane]yl, phenyl, naphthyl, dihydrobenzofuranyl, chromanyl, isochromanyl, 1,3-benzodioxolyl, dihydro-1,4-benzodioxinyl, tetrahydrobenzothiophenyl, furanyl, pyrazolyl, thienyl, pyridinyl, pyrimidinyl, indolyl, benzoxazolyl, benzimidazolyl, benzothienyl, imidazopyidinyl, quinolinyl, isoquinolinyl, phenyloxy or benzyloxy, wherein indanyl, tetrahydronaphthalenyl, spiro[cyclopropane-1,2-indane]yl, phenyl, naphthyl, dihydrobenzofuranyl, chromanyl, isochromanyl, 1,3-benzodioxolyl, dihydro-1,4-benzodioxinyl, tetrahydrobenzothiophenyl, furanyl, pyrazolyl, thienyl, pyridinyl, pyrimidinyl, indolyl, benzoxazolyl, imidazopyidinyl, quinolinyl, isoquinolinyl, phenyloxy and benzyloxy are optionally substituted with one to three substituents R.sup.6S, wherein R.sup.6S is independently halogen, cyano, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.2-C.sub.6-haloalkynyl, C.sub.1-C.sub.6-alkylsulfanyl, C.sub.1-C.sub.6-haloalkylsulfanyl, C.sub.3-C.sub.6-cycloalkyl, phenyl, pyrazolyl, imidazolyl, pyidinyl, oxetanyl, azetidinyl, terahydrofuranyl, pyrrolidinyl, tetrahydropyranyl, C(O)R.sup.16 or C(O)(OR.sup.17), wherein said C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl and C.sub.2-C.sub.6-haloalkynyl are furthermore optionally substituted with one or two substituents independently selected from the group consisting of cyano, hydroxyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, OSi(C.sub.1-C.sub.4-alkyl).sub.3, Si(C.sub.1-C.sub.4-alkyl).sub.3, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-halocycloalkyl, oxetanyl, azetidinyl, tetrahydrofuranyl, pyrrolidinyl and tetrahydropyranyl, and wherein said C.sub.3-C.sub.6-cycloalkyl, phenyl, pyrazolyl, imidazolyl, pyidinyl, oxetanyl, azetidinyl, terahydrofuranyl, pyrrolidinyl and tetrahydropyranyl are furthermore optionally substituted with one or two substituents independently selected from the group consisting of halogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl and C.sub.1-C.sub.6-alkoxycarbonyl, and wherein R.sup.16 is C.sub.1-C.sub.4-alkyl, R.sup.17 is hydrogen or C.sub.1-C.sub.4-alkyl, the ring Y is a group of formula (II-a), (II-b), (II-g), (II-h), (II-i), (II-r), (II-s), (II-u), (II-v), (II-ab) or (II-ac) ##STR00272## wherein * is the point of attachment to the group K-Q, # is the point of attachment to C(=T), A.sup.1 is CR.sup.8 or N, wherein R.sup.8 is hydrogen or methyl, G is O or NR.sup.7L, wherein R.sup.7L is hydrogen, q is 0, 1 or 2, x.sup.1 is 1 or 2, x.sup.2 is 0, 1 or 2, R.sup.7A is hydrogen, R.sup.7B is hydrogen, fluoro, methyl or methoxy, R.sup.7C is hydrogen, fluoro, methyl or methoxy, R.sup.7D is hydrogen, R.sup.7E is hydrogen, R.sup.7F is hydrogen, R.sup.7K is hydroxyl or methyl, R.sup.7L is hydrogen, halogen, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-hydroxyalkyl, C.sub.1-C.sub.4-alkylcarbonyl, C.sub.1-C.sub.4-haloalkylcarbonyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.2-C.sub.4-alkenyl, C.sub.2-C.sub.4-haloalkenyl, C.sub.2-C.sub.4-alkynyl, C.sub.2-C.sub.4-haloalkynyl, C.sub.1-C.sub.4-alkylsulfanyl, C.sub.1-C.sub.4-haloalkylsulfanyl, C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-haloalkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylsulfonyl C.sub.3-C.sub.6-cycloalkyl, phenyl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, N(R.sup.20).sub.2, C(NR.sup.21)R.sup.22, C(O)(OR.sup.25) or C(O)N(R.sup.26).sub.2, wherein C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-hydroxyalkyl, C.sub.1-C.sub.4-alkylcarbonyl, C.sub.1-C.sub.4-haloalkylcarbonyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.2-C.sub.4-alkenyl, C.sub.2-C.sub.4-haloalkenyl, C.sub.2-C.sub.4-alkynyl, C.sub.2-C.sub.4-haloalkynyl, C.sub.1-C.sub.4-alkylsulfanyl, C.sub.1-C.sub.4-haloalkylsulfanyl, C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-haloalkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl and C.sub.1-C.sub.6-haloalkylsulfonyl are optionally substituted with one to three substituents R.sup.7Sa, wherein C.sub.3-C.sub.6-cycloalkyl, phenyl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl, are optionally substituted with one to three substituents R.sup.7Sc, and wherein R.sup.20 is independently hydrogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl or C.sub.3-C.sub.8-cycloalkyl, wherein C.sub.3-C.sub.8-cycloalkyl, is optionally substituted with one or two substitutents independently selected from the group consisting of halogen and C.sub.1-C.sub.4-alkyl, R.sup.21 is hydroxyl, C.sub.1-C.sub.4-alkyl or C.sub.1-C.sub.4-alkoxy, R.sup.22 is hydrogen, C.sub.1-C.sub.4-alkyl or C.sub.1-C.sub.4-haloalkyl, R.sup.25 and R.sup.26 are independently hydrogen or C.sub.1-C.sub.4-alkyl, and wherein R.sup.7Sa is independently cyano, hydroxyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.4-alkoxycarbonyl, OSi(C.sub.1-C.sub.4-alkyl).sub.3 and phenyl, R.sup.7Sc is independently halogen, hydroxyl, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy or C.sub.1-C.sub.4-haloalkoxy, R.sup.7M is hydrogen, halogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.2-C.sub.4-alkenyl, C.sub.2-C.sub.4-haloalkenyl, C.sub.2-C.sub.4-alkynyl, C.sub.2-C.sub.4-haloalkynyl, C.sub.1-C.sub.4-alkylsulfanyl, C.sub.1-C.sub.4-haloalkylsulfanyl, C.sub.1-C.sub.4-alkylsulfinyl, C.sub.1-C.sub.4-haloalkylsulfinyl, C.sub.1-C.sub.4-alkylsulfonyl, C.sub.1-C.sub.4-haloalkylsulfonyl, C.sub.3-C.sub.6-cycloalkyl, phenyl, 3- to 7-membered heterocyclyl, 5- or 6-membered heteroaryl, C.sub.3-C.sub.6-cycloalkoxy, phenoxy, 3- to 7-membered heterocyclyloxy, 5- or 6-membered heteroaryloxy or N(R.sup.30).sub.2, wherein said C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.2-C.sub.4-alkenyl, C.sub.2-C.sub.4-haloalkenyl, C.sub.2-C.sub.4-alkynyl, C.sub.2-C.sub.4-haloalkynyl, C.sub.1-C.sub.4-alkylsulfanyl, C.sub.1-C.sub.4-haloalkylsulfanyl, C.sub.1-C.sub.4-alkylsulfinyl, C.sub.1-C.sub.4-haloalkylsulfinyl, C.sub.1-C.sub.4-alkylsulfonyl and C.sub.1-C.sub.4-haloalkylsulfonyl, are optionally substituted with one to three substituents R.sup.8Sa, said C.sub.3-C.sub.6-cycloalkyl, phenyl, 3- to 7-membered heterocyclyl, 5- or 6-membered heteroaryl, C.sub.3-C.sub.6-cycloalkoxy, phenoxy, 3- to 7-membered heterocyclyloxy and 5- or 6-membered heteroaryloxy are optionally substituted with one to three substituents R.sup.8Sc, and wherein R.sup.30 is hydrogen, C.sub.1-C.sub.4-alkyl, C.sub.2-C.sub.4-alkenyl, C.sub.2-C.sub.4-haloalkenyl, C.sub.3-C.sub.6-cycloalkyl or phenyl, wherein said C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.2-C.sub.4-alkenyl and C.sub.2-C.sub.4-haloalkenyl in turn are optionally substituted with one or two substituents R.sup.8Sa, said C.sub.3-C.sub.6-cycloalkyl and phenyl in turn are optionally substituted with one or two substituents R.sup.8Sc, and wherein R.sup.8Sa is independently selected from the group consisting of hydroxyl, carboxyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-alkoxycarbonyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.4-alkylsulfanyl, OSi(C.sub.1-C.sub.4-alkyl).sub.3, 3- to 7-membered heterocyclyl and N(R.sup.32).sub.2, wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one or two substituents independently selected from the group C.sub.1-C.sub.4-alkyl, R.sup.32 is independently hydrogen, formyl, C.sub.1-C.sub.4-alkyl or C.sub.1-C.sub.4-alkylcarbonyl, R.sup.8Sc is independently selected from the group consisting of halogen, cyano, hydroxyl, oxo, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-alkoxycarbonyl, C.sub.3-C.sub.6-cycloalkyl and 3- to 7-membered heterocyclyl, wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one or two substituents independently selected from the group C.sub.1-C.sub.6-alkyl, or two R.sup.8Sc substituents optionally form together with the carbon atom to which they are attached to a 3- to 7-membered heterocyclyl-ring, K is S(O).sub.p or S(O)NR.sup.44, wherein p is 0, 1 or 2, R.sup.44 is hydrogen or (C.sub.1-C.sub.4)-alkyl, Q is phenyl, napthyl, bicyclo[4.2.0]octa-1(6)2,4-trienyl, indanyl, tetrahydronaphthalenyl, indenyl, dihydronaphthalenyl, dihydrobenzofuranyl, dihydroisobenzofuranyl, indolinyl, 1,3-benzodioxolyl, chromanyl, dihydro-1,4-benzodioxinyl, [1,3]dioxolo[4,5-b]pyridinyl, tetrahydroquinolinyl, dihydro-5H-cyclopenta[b]pyridinyl, pyrrolyl, furanyl, thienyl, imidazolyl, triazolyl, oxazolyl, thiazolyl, pyridinyl, pyridazinyl, pyrimidinyl, indolyl, benzimidazolyl, indazolyl, benzofuranyl, benzothiophenyl, benzothiazolyl, benzoxazolyl, quinolinyl, furopyridinyl, thienothiophenyl or thienothiazolyl, wherein phenyl, napthyl, bicyclo[4.2.0]octa-1(6)2,4-trienyl, indanyl, tetrahydronaphthalenyl, indenyl, dihydronaphthalenyl, dihydrobenzofuranyl, dihydroisobenzofuranyl, indolinyl, 1,3-benzodioxolyl, chromanyl, dihydro-1,4-benzodioxinyl, [1,3]dioxolo[4,5-b]pyridinyl, tetrahydroquinolinyl, dihydro-5H-cyclopenta[b]pyridinyl, pyrrolyl, furanyl, thienyl, imidazolyl, triazolyl, oxazolyl, thiazolyl, pyridinyl, pyridazinyl, pyrimidinyl, indolyl, benzimidazolyl, indazolyl, benzofuranyl, benzothiophenyl, benzothiazolyl, benzoxazolyl, quinolinyl, furopyridinyl, thienothiophenyl and thienothiazolyl are optionally substituted with one to three substituents Q.sup.S wherein Q.sup.S is independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkylcarbonyl, C.sub.1-C.sub.4-haloalkylcarbonyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.2-C.sub.4-alkenyl, C.sub.2-C.sub.4-haloalkenyl, C.sub.2-C.sub.4-alkynyl, C.sub.2-C.sub.4-haloalkynyl, C.sub.1-C.sub.4-alkylsulfanyl, C.sub.1-C.sub.4-haloalkylsulfanyl, C.sub.3-C.sub.6-cycloalkyl, oxetanyl and N(R.sup.43).sub.2, wherein said C.sub.3-C.sub.6-cycloalkyl is optionally substituted with one or two substituents independently selected from the group consisting of halogen, C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-haloalkyl, and wherein R.sup.43 is independently hydrogen or C.sub.1-C.sub.4-alkyl, as well as their N-oxides, salts, solvates and solvates of the salts and N-oxides thereof.
3. The compounds of formula (I-A) according to claim 1, wherein T is O, n is 0 or 1, m is 0, 1 or 2, R.sup.1 is hydrogen or methyl, R.sup.2 and R.sup.3 are independently hydrogen or C.sub.1-C.sub.4-alkyl, R.sup.4 and R.sup.5 are independently hydrogen, fluoro or C.sub.1-C.sub.4-alkyl, or R.sup.2 and R.sup.4 form together with the carbon atom to which they are attached to a cyclopropyl ring, and R.sup.3 and R.sup.5 are independently hydrogen, R.sup.6 is indanyl or phenyl, wherein indanyl and phenyl are optionally substituted with one to three R.sup.6S substituents, wherein R.sup.6S is independently fluoro, chloro, C.sub.1-C.sub.4-alkyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.2-C.sub.6-haloalkynyl, methylsulfanyl, ethylsulfanyl, the ring Y is a group of formula (II-a), (II-r), (II-ab) or (II-ac) ##STR00273## wherein * is the point of attachment to the group K-Q, # is the point of attachment to C(=T), A.sup.1 is CR.sup.8 or N, wherein R.sup.8 is hydrogen, q is 0, x.sup.1 is 1 or 2, R.sup.7A is hydrogen, R.sup.7B is hydrogen, R.sup.7C is hydrogen, R.sup.7D is hydrogen, R.sup.7L is hydrogen, chloro or C.sub.1-C.sub.4-alkyl, R.sup.7M is hydrogen, K is S(O).sub.p or S(O)NR.sup.44, wherein p is 0, 1 or 2, R.sup.44 is hydrogen, methyl or ethyl, Q is phenyl or pyridyl, wherein phenyl and pyridyl are optionally substituted with one or two substituents Q.sup.S; wherein Q.sup.S is independently selected from the group consisting of fluoro, chloro C.sub.1-C.sub.4-alkyl, difluoromethyl, trifluoromethyl or C.sub.1-C.sub.4-alkoxy, as well as their salts, solvates and solvates of the salts thereof.
4. The compounds of formula (I-A) according to claim 1, wherein n is 1, m is 1, R.sup.1 is hydrogen, R.sup.2 and R.sup.3 are independently hydrogen or C.sub.1-C.sub.4-alkyl, R.sup.4 and R.sup.5 are independently hydrogen or fluoro.
5. The compounds of formula (I-A) according to claim 1, wherein K is S(O).sub.p, wherein p is 0, 1 or 2,
6. The compounds of formula (I-A) according to claim 1, wherein R.sup.6 is phenyl, optionally substituted with one or two substitutents R.sup.6S, wherein R.sup.6S is independently halogen, C.sub.1-C.sub.4-alkyl, difluoromethyl, trifluoro-methyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methylsulfanyl or ethylsulfanyl.
7. The compounds of formula (I-A) according to claim 1, wherein the ring Y is a group of formula (II-a), (II-r), (II-ab-1) or (II-ac) ##STR00274## wherein * is the point of attachment to the group K-Q, # is the point of attachment to C(=T), A.sup.1 is CR.sup.8 or N, wherein R.sup.8 is hydrogen, q is 0, X.sup.1 is 1 or 2, R.sup.7A is hydrogen, R.sup.7B is hydrogen, R.sup.7C is hydrogen, R.sup.7D is hydrogen, R.sup.7L is hydrogen, chloro or C.sub.1-C.sub.4-alkyl, R.sup.7M is hydrogen.
8. A composition for controlling phytopathogenic harmful fungi, comprising at least one compound of formula (I-A) according to claim 1 and at least one carrier and/or surfactant.
9. A method for controlling harmful microorganisms in crop protection and in the protection of materials, comprising the step of applying to the harmful microorganisms and/or their habitat at least one compound of formula (I-A) according to claim 1.
10. The use of one or more compounds of formula (I-A) according to claim 1 for controlling harmful microorganisms in crop protection and in the protection of materials.
11. A process for the preparation of compounds of formula (I-a) ##STR00275## wherein m, n, p, A.sup.1, Q, Y, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are defined as in claim 1 and T is O, R.sup.1 is hydrogen, hydroxyl, cyano or C.sub.1-C.sub.6-alkyl, comprising the step of reacting a compound of formula (1) ##STR00276## wherein m, n, p, A.sup.1, Q and Y are defined as in claim 1 and T is O, U.sup.1 is hydroxyl, halogen or C.sub.1-C.sub.6-alkoxy, with an amine of formula (2) ##STR00277## wherein m, n, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are defined as before or a salt thereof,
12. A process for the preparation of compounds of formula (I-a-2) ##STR00278## wherein m, n, A.sup.1, Q, Y, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are defined as in claim 1 and p is 0, T is O, R.sup.1 is hydrogen, C.sub.1-C.sub.6-alkyl or C.sub.1-C.sub.6-alkoxy, comprising the step of reacting a compound of formula (3) ##STR00279## wherein m, n, A.sup.1, Y, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are defined as in claim 1 and X.sup.1 is halogen, trifluoromethylsulfonyloxy or p-toluenesulfonyloxy, and a compound of formula (4) ##STR00280## wherein Q is defined as before, in the presence of a base.
13. A process for the preparation of compounds of formula (I-a-1) ##STR00281## wherein m, n, Q, Y, A.sup.1, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are defined as in claim 1 and T is O, p is 1 or 2, comprising the step of reacting a compound of formula (I-a-2) ##STR00282## wherein m, n, Q, T, Y, A.sup.1, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are defined as in claim 1, with an oxidizing reagent.
14. Process for the preparation of compounds of formula (I-c), ##STR00283## wherein m, n, p, A.sup.1, Q, Y, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are defined as in claim 1 and T is O, R.sup.1 is hydrogen, R.sup.44 is hydrogen or C.sub.1-C.sub.6-alkyl, comprising the step of reacting a compound of formula (1-f), ##STR00284## wherein m, n, R.sup.44, A.sup.1, T, Q and Y are defined as in claim 1 and U.sup.1 is hydroxyl, halogen or C.sub.1-C.sub.6-alkoxy, with an amine of formula (2), ##STR00285## wherein m, n, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are defined as in claim 1 or a salt thereof.
15. The compounds of formula (1) ##STR00286## wherein A.sup.1, Q, Y and p are defined as in claim 1 and U.sup.1 is hydroxyl, halogen or C.sub.1-C.sub.6-alkoxy, provided that the compound of formula (1) is not: 412339-07-2 3-phenylsulfanylpyridine-4-carboxylic acid 1513480-16-4 3-phenylsulfanylpyridazine-4-carboxylic acid 1872712-59-8 5-phenylsulfanylpyrimidine-4-carboxylic acid 847143-61-7 methyl 3-phenylsulfanylpyridine-4-carboxylate 1161865-36-6 methyl 2-(methylsulfanyl)-5-(phenylsulfonyl)pyrimidine-4-carboxylate 1161865-37-7 2-(methylsulfanyl)-5-(phenylsulfonyl)pyrimidine-4-carboxylic acid 1284425-70-2 2-isopropyl-5-(phenylsulfanyl)pyrimidine-4-carboxylic acid 1457455-96-7 2-isopropyl-5-[(3-methoxyphenyl)sulfanyl]pyrimidine-4-carboxylic acid 1457634-69-3 2-isopropyl-5-[(3-methylphenyl)sulfanyl]pyrimidine-4-carboxylic acid 1477890-40-6 5,6-dimethyl-3-(phenylsulfanyl)pyridazine-4-carboxylic acid 1481576-65-1 3-[(3-methoxyphenyl)sulfanyl]-5,6-dimethylpyridazine-4-carboxylic acid 1485756-76-0 3-[(3-chlorophenyl)sulfanyl]-5,6-dimethylpyridazine-4-carboxylic acid 1486392-94-2 5,6-dimethyl-3-[(3-methylphenyl)sulfanyl]pyridazine-4-carboxylic acid 1486802-49-6 3-[(3-bromophenyl)sulfanyl]-5,6-dimethylpyridazine-4-carboxylic acid 1492325-99-1 5-[(3-bromophenyl)sulfanyl]-2-isopropylpyrimidine-4-carboxylic acid 1497232-08-2 5-[(3-chlorophenyl)sulfanyl]-2-isopropylpyrimidine-4-carboxylic acid 1503006-13-0 5,6-diethyl-3-[(3-methylphenyl)sulfanyl]pyridazine-4-carboxylic acid 1503379-82-5 3-[(3-fluorophenyl)sulfanyl]-5,6-dimethylpyridazine-4-carboxylic acid 1506283-90-4 5-[(3-fluorophenyl)sulfanyl]-2-isopropylpyrimidine-4-carboxylic acid 1513271-93-6 3-[(3-methylphenyl)sulfanyl]isonicotinic acid 1514092-46-6 3-[(3-fluorophenyl)sulfanyl]isonicotinic acid 1523158-39-5 3-[(3-bromophenyl)sulfanyl]isonicotinic acid 1523548-82-4 3-[(3-methoxyphenyl)sulfanyl]pyridazine-4-carboxylic acid 1526683-76-0 3-[(3-methoxyphenyl)sulfanyl]isonicotinic acid 1534896-19-9 3-[(3-bromophenyl)sulfanyl]pyridazine-4-carboxylic acid 1534983-76-0 3-[(3-methylphenyl)sulfanyl]pyridazine-4-carboxylic acid 1535324-96-9 5,6-diethyl-3-[(3-fluorophenyl)sulfanyl]pyridazine-4-carboxylic acid 1536015-59-4 3-[(3-chlorophenyl)sulfanyl]isonicotinic acid 1540166-88-8 3-[(3-bromophenyl)sulfanyl]-5,6-diethylpyridazine-4-carboxylic acid 1540302-71-3 3-[(3-chlorophenyl)sulfanyl]-5,6-diethylpyridazine-4-carboxylic acid 1540390-44-0 5,6-diethyl-3-(phenylsulfanyl)pyridazine-4-carboxylic acid 1541162-68-8 3-[(3-fluorophenyl)sulfanyl]pyridazine-4-carboxylic acid 1983474-99-2 2-amino-5-[(3-chlorophenyl)sulfanyl]isonicotinic acid 1987381-07-6 methyl 2-amino-5-[(3-bromophenyl)sulfanyl]isonicotinate 1995464-60-2 5-[(3-fluorophenyl)sulfanyl]pyrimidine-4-carboxylic acid 2005209-39-0 5-[(3-bromophenyl)sulfanyl]pyrimidine-4-carboxylic acid 2023489-79-2 5-[(3-chlorophenyl)sulfanyl]pyrimidine-4-carboxylic acid 2153328-78-8 5-[(3-methylphenyl)sulfanyl]pyrimidine-4-carboxylic acid 25818-44-4 5-[(3-methylphenyl)sulfanyl]-2-(methylsulfanyl)pyrimidine-4-carboxylic acid 26032-75-7 5-[(3-chlorophenyl)sulfanyl]-2-(methylsulfanyl)pyrimidine-4-carboxylic acid 30314-53-5 5-[(3-methylphenyl)sulfonyl]-2-(methylsulfanyl)pyrimidine-4-carboxylic acid 30321-89-2 5-[(3-chlorophenyl)sulfonyl]-2-(methylsulfanyl)pyrimidine-4-carboxylic acid 392728-45-9 2-methyl-3-(phenylsulfanyl)quinoline-4-carboxylic acid 412337-18-9 2,6-dimethyl-3-(phenylsulfanyl)quinoline-4-carboxylic acid 61727-07-9 2-(methylsulfanyl)-5-(phenylsulfanyl)pyrimidine-4-carboxylic acid 61727-12-6 ethyl 2-(methylsulfanyl)-5-(phenylsulfanyl)pyrimidine-4-carboxylate 854861-13-5 2-methyl-3-[(3-methylphenyl)sulfanyl]quinoline-4-carboxylic acid 872284-02-1 2,6-dimethyl-3-[(3-methylphenyl)sulfanyl]quinoline-4-carboxylic acid 2773371-42-7 ethyl 3-(phenylsulfanyl)isonicotinate 2210255-71-1 methyl 3-[(2-amino-4-bromo-3-methylphenyl)sulfonyl]isonicotinate 2210255-70-0 methyl 3-[(4-bromo-3-methyl-2-nitrophenyl)sulfonyl]isonicotinate 2210255-69-7 methyl 3-[(4-bromo-3-methyl-2-nitrophenyl)sulfanyl]isonicotinate 2210255-66-4 3-[(2-amino-4-carboxyphenyl)sulfanyl]isonicotinic acid 2210255-65-3 3-[(4-carboxy-2-nitrophenyl)sulfanyl]isonicotinic acid 2210255-64-2 methyl 3-{[4-(methoxycarbonyl)-2-nitrophenyl]sulfanyl}isonicotinate 1984183-85-8 3-[(3,5-dichlorophenyl)sulfanyl]pyridazine-4-carboxylic acid 1973918-64-7 3-[(4-acetamidophenyl)sulfanyl]isonicotinic acid 1552208-23-7 3-(3,4-dihydro-2H-1,5-benzodioxepin-7-ylsulfanyl)pyridazine-4-carboxylic acid 1552187-93-5 3-(3,4-dihydro-2H-1,5-benzodioxepin-7-ylsulfanyl)isonicotinic acid 1549767-56-7 3-(2,3-dihydro-1,4-benzodioxin-6-ylsulfanyl)pyridazine-4-carboxylic acid 1546517-23-0 3-(2,3-dihydro-1,4-benzodioxin-6-ylsulfanyl)isonicotinic acid 1542446-95-6 5,6-diethyl-3-[(4-methylphenyl)sulfanyl]pyridazine-4-carboxylic acid 1541090-34-9 3-[(2,5-dichlorophenyl)sulfanyl]pyridazine-4-carboxylic acid as well as their N-oxides, salts, solvates and solvates of the salts and N-oxides thereof.
16. The compounds of formula (1-f) ##STR00287## wherein A.sup.1, Q and Y are defined as in claim 1 and T is oxygen K is S(O)NR.sup.44, wherein R.sup.44 is hydrogen or C.sub.1-C.sub.6-alkyl, U.sup.1 is hydroxyl, halogen or C.sub.1-C.sub.6-alkoxy.
17. The compounds of formula (1)
Q-SH(4), wherein Q is a group of formula ##STR00288## wherein .sup.1 is the point of attachment to sulfur, A.sup.3 is CH or N, Q.sup.S is C.sub.3-C.sub.4-cycloalkyl, C.sub.3-C.sub.8-halocycloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl, as well as their N-oxides, salts, solvates and solvates of the salts and N-oxides thereof.
Description
A. EXAMPLES
A-1. Generality
A-1.1. Measurement of Log P values
[1133] Measurement of Log P values as provided herein was performed according to EEC directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on reversed phase columns with the following methods: [1134] .sup.[a] Log P value is determined by measurement of LC-UV, in an acidic range, with 0.1% formic acid in water and acetonitrile as eluent (linear gradient from 10% acetonitrile to 95% acetonitrile). [1135] .sup.[b] Log P value is determined by measurement of LC-UV, in a neutral range, with 0.001 molar ammonium acetate solution in water and acetonitrile as eluent (linear gradient from 10% acetonitrile to 95% acetonitrile). [1136] .sup.[c] Log P value is determined by measurement of LC-UV, in an acidic range, with 0.1% phosphoric acid and acetonitrile as eluent (linear gradient from 10% acetonitrile to 95% acetonitrile).
[1137] If more than one Log P value is available within the same method, all the values are given and separated by +.
[1138] Calibration was done with straight-chain alkan2-ones (with 3 to 16 carbon atoms) with known Log P values (measurement of Log P values using retention times with linear interpolation between successive alkanones). Lambda-max-values were determined using UV-spectra from 200 nm to 400 nm and the peak values of the chromatographic signals
A-1.2. .SUP.1.H-NMR Data
[1139] .sup.1H-NMR data of selected examples as provided herein are written in form of .sup.1H-NMR-peak lists. To each signal peak are listed the -value in ppm and the signal intensity in round brackets. Between the -valuesignal intensity pairs are semicolons as delimiters.
[1140] The peak list of an example has therefore the form: [1141] .sub.1 (intensity.sub.1); .sub.2 (intensity.sub.2); . . . ; .sub.i (intensity.sub.i); . . . ; .sub.n (intensity.sub.n)
[1142] Intensity of sharp signals correlates with the height of the signals in a printed example of a NMR spectrum in cm and shows the real relations of signal intensities. From broad signals several peaks or the middle of the signal and their relative intensity in comparison to the most intensive signal in the spectrum can be shown.
[1143] For calibrating chemical shift for .sup.1H spectra, we use tetramethylsilane and/or the chemical shift of the solvent used, especially in the case of spectra measured in DMSO. Therefore in NMR peak lists, tetramethylsilane peak can occur but not necessarily.
[1144] The .sup.1H-NMR peak lists are similar to classical .sup.1H-NMR prints and contains therefore usually all peaks, which are listed at classical NMR-interpretation.
[1145] Additionally they can show like classical .sup.1H-NMR prints signals of solvents, stereoisomers of the target compounds, which are also object of the invention, and/or peaks of impurities.
[1146] To show compound signals in the delta-range of solvents and/or water the usual peaks of solvents, for example peaks of DMSO in DMSO-D.sub.6 and the peak of water are shown in our .sup.1H-NMR peak lists and have usually on average a high intensity.
[1147] The peaks of stereoisomers of the target compounds and/or peaks of impurities have usually on average a lower intensity than the peaks of target compounds (for example with a purity >90%).
[1148] Such stereoisomers and/or impurities can be typical for the specific preparation process. Therefore their peaks can help to recognize the reproduction of our preparation process via side-products-fingerprints.
[1149] An expert, who calculates the peaks of the target compounds with known methods (MestreC, ACD-simulation, but also with empirically evaluated expectation values) can isolate the peaks of the target compounds as needed optionally using additional intensity filters. This isolation would be similar to relevant peak picking at classical .sup.1H-NMR interpretation.
[1150] Further details of NMR-data description with peak lists you find in the publication Citation of NMR Peaklist Data within Patent Applications of the Research Disclosure Database Number 564025.
[1151] The following examples illustrate in a non-limiting manner the preparation and biological activity of the compounds of formula (I-A) according to the invention.
A-3. Synthesis of Compounds of Formula (I-A) and Intermediates
Preparation example 1: preparation of 6-chloro-N-[2-(2,4-dichlorophenyl)-2,2-difluoroethyl]-3-{[3-(trifluoromethyl)phenyl]sulfanyl}pyridazine-4-carboxamide (Compound I-082)
[1152] To a stirred solution of 3,6-dichloro-N-[2-(2,4-dichlorophenyl)-2,2-difluoroethyl]pyridazine-4-carboxamide [2435608-03-8] (500 mg, 1.24 mmol) in DMF (5 mL) were added at room temperature potassium carbonate (206 mg g, 1.49 mol) and 3-(trifluoromethyl)benzenethiol (244 mg, 1.37 mmol). The reaction mixture was stirred for 18 h at room temperature. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic extracts were dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification of the residue by column chromatography on silica gel (gradient heptane/ethyl acetate) afforded, after evaporation of the solvents 580 mg (80% purity, 68% yield) of 6-chloro-N-[2-(2,4-dichlorophenyl)-2,2-difluoroethyl]-3-{[3-(trifluoromethyl)phenyl]sulfanyl}pyridazine-4-carboxamide as a solid.
Preparation example 2: preparation of 6-chloro-N-[2-(2,4-dichlorophenyl)-2,2-difluoroethyl]-3-{[3-(trifluoromethyl)phenyl]sulfanyl}pyridazine-4-carboxamide (Compound I-018) and 6-chloro-N-[2-(2,4-dichlorophenyl)-2,2-difluoroethyl]-3-{[3-(trifluoromethyl)phenyl]sulfonyl}pyridazine-4-carboxamide (Compound I-019)
[1153] To a stirred solution of 6-chloro-N-[2-(2,4-dichlorophenyl)-2,2-difluoroethyl]-3-{[3-(trifluoro-methyl)phenyl]sulfanyl}pyridazine-4-carboxamide (70 mg, 0.12 mmol) in 2 mL dichloromethane was added meta-chloroperbenzoic acid (69 mg, 70% purity, 0.28 mmol). The reaction mixture was stirred at room temperature until total conversion of the starting material. The reaction mixture was quenched with an aqueous solution of sodium bicarbonate and extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by preparative HPLC to separately afford 30 mg (90% purity, 37% yield) of 6-chloro-N-[2-(2,4-dichlorophenyl)-2,2-difluoroethyl]-3-{[3-(trifluoromethyl)phenyl]sulfanyl}pyridazine-4-carboxamide (compound I-018) and 12 mg (90% purity, 14% yield) of preparation of 6-chloro-N-[2-(2,4-dichlorophenyl)-2,2-difluoroethyl]-3-{[3-(trifluoromethyl)phenyl]sulfonyl}pyridazine-4-carboxamide (compound I-019).
Preparation example 3: N-[2-(2,4-dimethylphenyl)ethyl]-6-[(3-methoxyphenyl)sulfanyl]-3-methyl-1,2,4-triazine-5-carboxamide (Compound I-080)
Step 1: Preparation of ethyl 6-[(3-methoxyphenyl)sulfanyl]-3-methyl-1,2,4-triazine-5-carboxylate (Compound 1-01)
[1154] In a microwave vial, a mixture of ethyl 6-chloro-3-methyl-1,2,4-triazine-5-carboxylate (80 mg, 0.39 mmol), 3-methoxybenzenethiol (72 mg, 0.51 mmol), 1-butyl-1H-imidazole (24 mg, 0.19 mmol), copper iodide (7 mg, 0.04 mmol) and cesium carbonate (258 mg, 0.79 mmol) were suspended in dry toluene (3.6 mL). The tube was sealed, and the reaction mixture was heated under microwave irradiation at 120 C. for 16 h. The crude reaction mixture was poured on a silica gel cartridge and eluted twice with 8 mL dichloromethane. After evaporation of the solvents, the crude product was purified by preparative HPLC to afford 51 mg (98% purity, 41% yield) of ethyl 6-[(3-methoxyphenyl)sulfanyl]-3-methyl-1,2,4-triazine-5-carboxylate.
Step 2: Preparation of N-[2-(2,4-dimethylphenyl)ethyl]-6-[(3-methoxyphenyl)sulfanyl]-3-methyl-1,2,4-triazine-5-carboxamide (Compound I-080)
[1155] To a stirred solution under argon of ethyl 6-[(3-methoxyphenyl)sulfanyl]-3-methyl-1,2,4-triazine-5-carboxylate (50 mg, 0.16 mmol) in 0.5 mL THF, was added at room temperature bis(trimethylaluminum)-1,4-diazabicyclo[2.2.2]octane adduct [137203-34-0] (52 mg, 0.20 mmol). After 5 min stirring, a solution of 2-(2,4-dimethylphenyl)ethanamine [76935-60-9] (32 mg, 0.21 mmol) in 0.3 mL dichloromethane was added. The reaction mixture was stirred during 16 h at room temperature. The reaction mixture was diluted with ethyl acetate and quenched with water then acidify with 1 M aqueous hydrochloric acid. The mixture was extracted with ethyl acetate, and the combined organic layers were dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification of the residue by column chromatography on silica gel (gradient heptane/ethyl acetate) afforded 65 mg (99% purity, 97% yield) of the title compound.
Preparation example 4: 6-methyl-N-(2-phenylethyl)-3-{(R,S)-[3-(trifluoromethyl)phenyl]sulfonimidoyl}pyridazine-4-carboxamide (Compound I-159)
Step 1: Preparation of methyl 6-chloro-3-{[3-(trifluoromethyl)phenyl]sulfanyl}pyridazine-4-carboxylate (Compound 1-04)
[1156] To a stirred solution of methyl 3,6-dichloropyridazine-4-carboxylate [286946-24-5] (10 g, 48.3 mmol) and 3-(trifluoromethyl)benzenethiol [937-00-8] (7.75 g, 43.4 mmol) in toluene (100 mL) was added K.sub.2CO.sub.3 (20.03 g, 144.9 mmol) in portions at room temperature under nitrogen atmosphere during 3 hours. The resulting mixture was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous Na.sub.2SO.sub.4. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography, eluted with petroleum ether/ethyl acetate (10:1) to afford methyl 6-chloro-3-{[3-(trifluoromethyl)phenyl]sulfanyl}pyridazine-4-carboxylate (15.3 g, 90% yield).
Step 2: Preparation of methyl 6-methyl-3-{[3-(trifluoromethyl)phenyl]sulfanyl}pyridazine-4-carboxylate (Compound 1-05)
[1157] To a stirred solution of methyl 6-chloro-3-{[3-(trifluoromethyl)phenyl]sulfanyl}pyridazine-4-carboxylate (33 g, 94.6 mmol) and trimethyl-1,3,5,2,4,6-trioxatriborinane [823-96-1] (95.03 g, 378.5 mmol, 50%) in dioxane (300 mL) were added CsF (43.12 g, 283.8 mmol) and Pd(dppf)Cl.sub.2CH.sub.2Cl.sub.2 [95464-05-4] (7.71 g, 9.4 mmol) in portions at room temperature under nitrogen atmosphere. The resulting mixture was stirred overnight at 75 C. under nitrogen atmosphere. The mixture was allowed to cool down to room temperature. The resulting mixture was extracted with ethyl acetate. The combined organic layers were washed with brine and dried over anhydrous Na.sub.2SO.sub.4. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography, eluted with petroleum ether/ethyl acetate (8:1) to afford methyl 6-methyl-3-{[3-(trifluoromethyl)phenyl]sulfanyl}pyridazine-4-carboxylate (27 g, 86% yield).
Step 3: Preparation of methyl 6-methyl-3-{(R,S)-[3-(trifluoromethyl)phenyl]sulfonimidoyl}pyridazine-4-carboxylate (Compound 1f-05)
[1158] To a stirred solution of methyl 6-methyl-3-{[3-(trifluoromethyl)phenyl]sulfanyl}pyridazine-4-carboxylate (10 g, 30.4 mmol) and ammonium carbamate [1111-78-0] (3.57 g, 45.7 mmol) in methanol (100 mL) was added iodobenzene diacetate [3240-34-4] (20.60 g, 63.9 mmol) in portions at room temperature under nitrogen atmosphere. The resulting mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography, eluted with petroleum ether/ethyl acetate (10:1) to afford the title compound (8 g, 73% yield).
Step 4: Preparation of 6-methyl-3-{(R,S)-[3-(trifluoromethyl)phenyl]sulfonimidoyl}pyridazine-4-carboxylic acid (Compound 1f-03)
[1159] A solution of methyl 6-methyl-3-{(R,S)-[3-(trifluoromethyl)phenyl]sulfonimidoyl}pyridazine-4-carboxylate (8 g, 22.3 mmol) and LiOH (22.26 mL, 44.5 mmol) in THF (80 mL) was stirred overnight at room temperature under nitrogen atmosphere. The mixture was acidified to pH 2 with an aqueous solution of HCl. The precipitated solids were collected by filtration and washed with water to afford 5.83 g of the tittle compound (72% yield).
Step 5: Preparation of 6-methyl-N-(2-phenylethyl)-3-{(R,S)-[3-(trifluoromethyl)phenyl]sulfonimidoyl}pyridazine-4-carboxamide (Compound I-159)
[1160] To a solution of 6-methyl-3-{(R,S)-[3-(trifluoromethyl)phenyl]sulfonimidoyl}pyridazine-4-carboxylic acid (100 mg, 0.29 mmol) and 2-phenylethanamine (42 mg, 0.34 mmol) in 1 mL THF was added a 1 mL THF solution of pyridine (1.16 mmol) and propanephosphonic acid anhydride [68957-94-8] (0.5 mL, 0.58 mmol, 50% wt in THF). The reaction mixture was stirred at room temperature during 16 hours, then poured onto a 2 g Alox cartridge and eluted twice with 8 mL dichloromethane. After evaporation of the solvent, the crude residue was purified using prep-HPLC/MS (SunFire Waters 5 m 30150 acetonitrile/H.sub.2O (0.1% formic acid)) to afford 19 mg of the title compound (90% purity, 13% yield).
Preparation example 5: 6-methyl-3-{N-methyl-(R,S)-[3-(trifluoromethyl)phenyl]sulfonimidoyl}-N-(2-phenylethyl)pyridazine-4-carboxamide (Compound I-174)
Step 1: Preparation of 6-methyl-3-{N-methyl-(R,S)-[3-(trifluoromethyl)phenyl]sulfonimidoyl}pyridazine-4-carboxylic acid (Compound 1f-01)
[1161] To a solution of methyl 6-methyl-3-{(R,S)-[3-(trifluoromethyl)phenyl]sulfonimidoyl}pyridazine-4-carboxylate (10 g, 27.8 mmol) in DMF (100 mL) was treated with NaH (2.23 g, 55.6 mmol, 60%) at 0 C. under nitrogen atmosphere. The solution was stirred at 0 C. for 30 minutes. Then methyliodide (11.85 g, 83.5 mmol) was added at 0 C. The solution was stirred at room temperature. The reaction was quenched with a saturated aqueous solution of NH.sub.4Cl at room temperature. The resulting mixture was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous Na.sub.2SO.sub.4. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography, eluted with petroleum ether/ethyl acetate (10:1) to afford 2.1 g of methyl 6-methyl-3-{N-methyl-(R,S)-[3-(trifluoromethyl)phenyl]sulfonimidoyl}pyridazine-4-carboxylate (20% yield).
[1162] A solution of methyl 6-methyl-3-{N-methyl-(R,S)-[3-(trifluoromethyl)phenyl]sulfonimidoyl}pyridazine-4-carboxylate (3 g, 8.0 mmol) and LiOH (0.38 g, 16.070 mmol, 2 equiv) in THF (30 mL) and H.sub.2O (8 mL) was stirred for overnight at room temperature under nitrogen atmosphere. The residue was acidified to pH 2 with an aqueous solution of HCl. The resulting mixture was extracted with ethyl acetate. The combined organic layers were washed with brine and dried over anhydrous Na.sub.2SO.sub.4. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by reversed-phase flash chromatography with the following conditions: column, C.sub.18 silica gel; mobile phase, acetonitrile in H.sub.2O (0.1% formic acid, 0% to 100% gradient in 30 min; detector, UV 254 nm. This afforded 1.8 g of the title compound (57% yield).
Step 2: Preparation of 6-methyl-3-{N-methyl-(R,S)-[3-(trifluoromethyl)phenyl]sulfonimidoyl}-N-(2-phenylethyl)pyridazine-4-carboxamide (Compound I-174)
[1163] To a solution of 6-methyl-3-{N-methyl-(R,S)-[3-(trifluoromethyl)phenyl]sulfonimidoyl}pyridazine-4-carboxylic acid (104 mg, 0.29 mmol) and 2-phenylethanamine (42 mg, 0.34 mmol) in 1 mL THF was added a 1 mL THF solution of pyridine (1.16 mmol) and propanephosphonic acid anhydride [68957-94-8] (0.5 mL, 0.58 mmol, 50% wt in THF). The reaction mixture was stirred at room temperature for 16 hours, then poured onto a 2 g Alox cartridge and eluted twice with 8 mL dichloromethane. After evaporation of the solvent, the crude residue was purified using prep-HPLC/MS (SunFire Waters 5 m 30150 acetonitrile/H.sub.2O (0.1% formic acid)) to afford 16 mg of the title compound (99% purity, 11% yield).
[1164] The compounds of formula (I-A) in table 1 were prepared according to the procedures described above.
[1165] Table 1: Compounds of formula (I-A)
##STR00046##
TABLE-US-00001 TABLE 1 Compounds according to formula (I-A), their .sup.1H-NMR data and LogP values Ex N Structure .sup.1H-NMR Peak List LogP I- 001 [00047]
.sup.1H-NMR(400.2 MHz, d6-DMSO): = 9.0788 (0.7); 9.0657 (1.5); 9.0517 (0.8); 7.8465 (7.2); 7.5683 (0.6); 7.5594 (0.6); 7.5446 (16.0); 7.5218 (0.6); 7.5201 (0.6); 7.4726 (1.2); 7.4529 (2.6); 7.4331 (1.9); 7.3508 (2.0); 7.3315 (1.5); 7.2928 (2.4); 7.2242 (1.4); 7.2036 (1.1); 5.7596 (2.1); 3.5677 (0.9); 3.5504 (2.4); 3.5355 (2.5); 3.5186 (1.1); 3.3431 (138.0); 2.9395 (1.8); 2.9220 (3.6); 2.9045 (1.6); 2.6767 (0.4); 2.6723 (0.6); 2.6679 (0.5); 2.5256 (2.1); 2.5077 (76.9); 2.5033 (101.3); 2.4989 (77.8); 2.3344 (0.4); 2.3302 (0.6); 2.3258 (0.5); 0.0002 (2.1) 4.37.sup.[a] I- 002 [00048]
3.55.sup.[a] I- 003 [00049]
3.85.sup.[a] I- 004 [00050]
.sup.1H-NMR(400.2 MHz, d6-DMSO): = 9.1288 (1.4); 9.1146 (2.8); 9.1006 (1.4); 7.8551 (16.0); 7.5706 (0.5); 7.5614 (3.9); 7.5555 (4.9); 7.5464 (6.6); 7.5372 (7.0); 7.5253 (0.8); 7.5207 (0.3); 7.5019 (0.4); 7.4933 (2.2); 7.4839 (15.9); 7.4779 (12.1); 7.4720 (5.3); 7.4698 (6.2); 7.4671 (7.2); 7.4645 (5.3); 7.4590 (4.1); 7.4455 (5.0); 7.4410 (4.9); 7.4365 (3.2); 7.4313 (3.5); 7.4179 (3.5); 7.4132 (4.1); 7.3326 (1.4); 7.3285 (1.8); 7.3142 (4.2); 7.3101 (4.1); 7.2962 (6.8); 7.2906 (5.5); 7.2769 (3.7); 7.2719 (3.5); 7.2583 (1.3); 7.2536 (1.1); 5.7557 (2.4); 3.5606 (2.3); 3.5436 (4.7); 3.5282 (4.7); 3.5103 (2.6); 3.4760 (0.4); 3.3774 (630.4); 3.2688 (0.4); 3.1760 (0.4); 3.1631 (0.4); 3.0155 (4.4); 2.9972 (7.4); 2.9795 (3.9); 2.6786 (0.8); 2.6742 (1.1); 2.6696 (0.8); 2.6650 (0.4); 2.5275 (3.6); 2.5227 (5.7); 2.5141 (66.7); 2.5097 (136.6); 2.5051 (178.9); 2.5006 (125.5); 2.4961 (58.0); 2.3409 (0.4); 2.3365 (0.8); 2.3319 (1.1); 2.3273 (0.8); 2.3226 (0.4) 3.63.sup.[a] I- 005 [00051]
.sup.1H-NMR(400.2 MHz, d6-DMSO): = 9.0523 (0.6); 9.0389 (1.2); 9.0247 (0.6); 7.8680 (5.8); 7.5782 (1.1); 7.5720 (0.7); 7.5624 (1.0); 7.5562 (6.9); 7.5463 (7.1); 7.5306 (0.6); 7.5241 (1.2); 7.2070 (3.0); 7.1855 (3.4); 6.8823 (3.7); 6.8608 (3.4); 5.7591 (1.0); 3.7091 (16.0); 3.4854 (0.8); 3.4683 (1.7); 3.4513 (1.7); 3.4348 (0.9); 3.3461 (80.6); 2.8074 (1.5); 2.7888 (2.5); 2.7708 (1.4); 2.6720 (0.4); 2.5074 (48.2); 2.5032 (62.8); 2.4989 (47.0); 2.3302 (0.4); 0.0002 (1.5) 3.68.sup.[a] I- 006 [00052]
3.09.sup.[a] I- 007 [00053]
4.23.sup.[a] I- 008 [00054]
.sup.1H-NMR(400.2 MHz, d6-DMSO): = 9.5485 (1.4); 9.5342 (2.8); 9.5197 (1.4); 8.0658 (16.0); 7.6945 (5.6); 7.6896 (6.0); 7.6530 (6.5); 7.6323 (7.8); 7.5873 (0.6); 7.5779 (3.7); 7.5722 (4.9); 7.5629 (5.5); 7.5538 (6.3); 7.5414 (0.6); 7.5036 (0.4); 7.4942 (1.8); 7.4848 (13.0); 7.4791 (10.9); 7.4710 (5.9); 7.4679 (6.1); 7.4586 (1.4); 7.4488 (0.4); 7.4445 (0.4); 7.4211 (3.4); 7.4161 (3.4); 7.4005 (2.8); 7.3954 (2.9); 5.7595 (4.7); 4.5093 (7.5); 4.4947 (7.5); 3.3407 (257.7); 3.1679 (0.6); 2.6762 (1.0); 2.6718 (1.4); 2.6672 (1.1); 2.5252 (4.4); 2.5205 (6.4); 2.5116 (84.2); 2.5073 (178.9); 2.5028 (240.7); 2.4983 (174.2); 2.4939 (84.3); 2.3385 (0.5); 2.3341 (1.0); 2.3296 (1.4); 2.3251 (1.1); 1.2343 (0.7); 0.0079 (0.5); 0.0002 (16.1); 0.0084 (0.6) 3.85.sup.[a] I- 009 [00055]
.sup.1H-NMR(400.2 MHz, d6-DMSO): = 9.0349 (0.6); 9.0213 (1.3); 9.0074 (0.6); 7.8626 (6.3); 7.5746 (1.0); 7.5676 (0.7); 7.5591 (0.9); 7.5523 (8.4); 7.5455 (9.0); 7.5302 (0.6); 7.5231 (1.0); 6.8843 (2.1); 6.8781 (2.7); 6.8735 (3.0); 6.8640 (3.1); 6.7936 (1.6); 6.7893 (1.6); 6.7733 (1.0); 6.7687 (1.1); 5.7576 (1.4); 3.7440 (15.8); 3.7035 (16.0); 3.5126 (0.8); 3.4955 (1.8); 3.4790 (1.8); 3.4626 (0.9); 3.4140 (0.5); 3.3604 (186.6); 2.8057 (1.5); 2.7875 (2.7); 2.7700 (1.4); 2.6733 (0.5); 2.5265 (1.4); 2.5086 (56.1); 2.5042 (75.1); 2.4998 (57.4); 2.3310 (0.4); 2.3266 (0.3); 0.0002 (1.3) 3.29.sup.[a] I- 010 [00056]
.sup.1H-NMR(400.2 MHz, d6-DMSO): = 9.1513 (1.5); 9.1380 (2.9); 9.1246 (1.6); 7.8906 (13.1); 7.5815 (3.0); 7.5754 (1.9); 7.5595 (16.0); 7.5485 (15.8); 7.5323 (1.9); 7.5264 (3.0); 7.4623 (3.1); 7.4589 (2.9); 7.4437 (4.1); 7.4398 (3.9); 7.4287 (2.8); 7.4241 (2.9); 7.4099 (3.6); 7.4061 (3.8); 7.3323 (1.3); 7.3285 (1.4); 7.3139 (3.7); 7.3102 (3.4); 7.2956 (5.1); 7.2913 (4.5); 7.2758 (3.1); 7.2712 (2.9); 7.2573 (1.1); 7.2527 (1.0); 5.7568 (1.9); 3.5599 (1.9); 3.5431 (4.8); 3.5271 (4.9); 3.5098 (2.4); 3.4762 (0.4); 3.3718 (561.4); 3.2806 (0.5); 3.2572 (0.3); 3.0123 (3.9); 2.9943 (6.9); 2.9765 (3.5); 2.6739 (1.1); 2.5091 (155.1); 2.5050 (185.0); 2.5012 (140.0); 2.3360 (0.9); 2.3318 (1.1); 0.0002 (1.2) 4.13.sup.[a] I- 011 [00057]
.sup.1H-NMR(400.1 MHz, CDCl3): = 8.5241 (1.0); 8.2426 (5.7); 7.5663 (0.3); 7.5618 (0.6); 7.5573 (0.4); 7.5110 (6.0); 7.4545 (0.3); 7.4360 (0.5); 7.4319 (0.4); 7.4103 (0.4); 7.4060 (0.5); 7.3856 (0.6); 7.3665 (0.5); 7.2999 (0.4); 7.2959 (0.8); 7.2914 (0.7); 7.2799 (1.9); 7.2757 (3.6); 7.2711 (4.2); 7.2604 (14.7); 7.2526 (3.3); 7.2383 (3.6); 7.2334 (2.8); 7.1365 (1.4); 7.1324 (2.3); 7.1279 (1.2); 7.1185 (1.1); 7.1145 (1.8); 7.1102 (1.0); 7.0650 (1.2); 7.0231 (1.9); 7.0033 (5.0); 6.9543 (2.1); 6.9345 (1.3); 6.4718 (0.8); 5.2996 (0.9); 3.6492 (0.6); 3.6369 (1.6); 3.6195 (3.2); 3.6047 (3.2); 3.5871 (1.6); 2.9103 (0.4); 2.8927 (0.8); 2.8745 (0.5); 2.8639 (2.2); 2.8463 (4.3); 2.8285 (2.1); 2.2986 (16.0); 2.2896 (15.6); 4.85.sup.[a] 1.5615 (3.9); 1.2543 (0.6); 0.0696 (1.1); 0.0078 (0.8); 0.0002 (16.6); 0.0082 (0.9) I- 012 [00058]
3.46.sup.[a] I- 013 [00059]
.sup.1H-NMR(400.2 MHz, d6-DMSO): = 9.0440 (1.5); 9.0299 (3.1); 9.0152 (1.6); 7.9513 (15.2); 7.5838 (4.6); 7.5788 (2.2); 7.5622 (15.9); 7.5437 (16.0); 7.5275 (2.0); 7.5219 (4.8); 7.4386 (3.3); 7.4353 (3.4); 7.4196 (4.1); 7.4162 (4.4); 7.3849 (2.4); 7.3807 (2.8); 7.3663 (3.8); 7.3623 (4.2); 7.3122 (1.5); 7.3090 (1.8); 7.2940 (3.8); 7.2907 (3.9); 7.2759 (2.6); 7.2687 (3.5); 7.2636 (3.1); 7.2493 (3.2); 7.2449 (3.2); 7.2307 (1.2); 7.2265 (1.1); 5.7597 (2.3); 3.3969 (0.4); 3.3805 (0.6); 3.3441 (294.9); 3.2458 (3.8); 3.2301 (7.2); 3.2147 (4.1); 2.8928 (1.9); 2.8778 (2.0); 2.8593 (2.4); 2.8442 (2.4); 2.6766 (0.7); 2.6727 (0.9); 2.5840 (2.3); 2.5629 (2.7); 2.5505 (2.2); 2.5263 (3.5); 2.5077 (113.3); 2.5036 (147.8); 2.4994 (110.8); 2.3305 (0.9); 2.1377 (0.4); 2.1210 (1.0); 2.1038 4.67.sup.[a] (1.6); 2.0856 (1.5); 2.0684 (1.0); 2.0517 (0.4); 0.9161 (14.1); 0.8994 (13.7); 0.0002 (1.2) I- 014 [00060]
.sup.1H-NMR(400.1 MHz, CDCl3): = 8.1691 (6.2); 8.1681 (5.8); 7.5239 (6.6); 7.5228 (6.1); 7.2598 (10.3); 7.2453 (1.2); 7.2263 (2.9); 7.2073 (2.1); 7.1391 (1.9); 7.1201 (1.4); 7.1188 (1.4); 7.1058 (2.9); 7.0906 (1.8); 7.0893 (1.8); 7.0713 (1.4); 7.0700 (1.4); 7.0325 (2.1); 7.0133 (3.2); 6.9933 (2.8); 6.9493 (1.8); 6.9301 (1.2); 6.6213 (0.8); 3.6331 (1.5); 3.6154 (3.0); 3.6007 (3.0); 3.5826 (1.7); 2.8601 (2.4); 2.8422 (4.3); 2.8243 (2.2); 2.3139 (15.0); 2.3013 (16.0); 2.2840 (14.5); 1.5675 (3.6); 0.0699 (0.8); 0.0079 (0.5); 0.0002 (12.1); 0.0085 (0.5) 4.81.sup.[a] I- 015 [00061]
2.80.sup.[a] I- 016 [00062]
3.63.sup.[a] I- 017 [00063]
3.13.sup.[a] I- 018 [00064]
.sup.1H-NMR(499.9 MHz, MeOD): = 8.2696 (2.8); 8.1597 (1.6); 8.1438 (1.7); 7.8200 (9.1); 7.7566 (1.4); 7.7411 (1.8); 7.6609 (1.5); 7.6452 (2.4); 7.6294 (1.1); 7.6172 (3.0); 7.6001 (3.5); 7.5449 (2.6); 7.5412 (2.8); 7.4421 (10.0); 7.3935 (1.8); 7.3895 (1.7); 7.3765 (1.6); 7.3726 (1.5); 7.0876 (0.4); 7.0720 (0.8); 7.0623 (0.5); 7.0563 (0.5); 6.9932 (0.4); 6.6140 (0.3); 6.6107 (0.4); 6.6091 (0.4); 6.5977 (0.6); 6.5948 (0.7); 6.5800 (0.4); 6.5425 (0.5); 6.5385 (0.7); 6.5346 (0.4); 5.3454 (0.9); 4.3546 (0.3); 4.3253 (1.0); 4.2931 (1.3); 4.2856 (0.8); 4.2659 (1.0); 4.2612 (1.4); 4.2528 (1.0); 4.2399 (16.0); 4.1992 (0.4); 3.3615 (3.8); 3.3585 (5.2); 3.3555 (3.8); 2.0559 (0.8); 2.0455 (1.2); 1.8310 (0.4); 1.2845 (0.4); 1.2700 (1.0); 1.2664 (0.9); 1.2560 (0.3); 0.9837 (1.6); 0.9310 (0.8); 0.9270 3.92.sup.[a] (0.8); 0.9233 (0.4); 0.9182 (0.4); 0.9140 (0.8); 0.9076 (2.0); 0.9015 (0.4); 0.6701 (0.8); 0.6665 (0.7); 0.6602 (0.7); 0.6566 (0.8); 0.1911 (1.1); 0.0706 (1.3); 0.0002 (8.4); 0.0067 (0.3) I- 019 [00065]
.sup.1H-NMR(400.1 MHz, CDCl3): = 8.3467 (0.6); 8.3242 (5.9); 8.2606 (3.3); 8.2406 (3.5); 7.9951 (3.1); 7.9755 (3.8); 7.7925 (2.7); 7.7727 (4.8); 7.7507 (16.0); 7.6607 (5.4); 7.6394 (6.2); 7.5213 (6.1); 7.3825 (3.7); 7.3780 (3.5); 7.3613 (3.2); 7.3567 (3.0); 7.3095 (1.5); 7.2948 (2.6); 7.2798 (1.5); 7.2602 (14.9); 4.4611 (2.4); 4.4455 (2.3); 4.4246 (5.0); 4.4090 (4.9); 4.3880 (2.6); 4.3724 (2.5); 4.1216 (0.6); 4.1037 (0.7); 4.0729 (0.9); 4.0563 (1.5); 4.0396 (0.8); 2.0514 (0.6); 2.0381 (7.4); 1.6412 (0.8); 1.6237 (1.8); 1.6067 (2.8); 1.5879 (2.3); 1.5711 (1.2); 1.4270 (0.5); 1.4092 (0.6); 1.3895 (0.7); 1.3709 (0.7); 1.3527 (0.5); 1.3340 (0.3); 1.2927 (0.5); 1.2732 (1.3); 1.2555 (3.9); 1.2375 (1.1); 1.2219 (0.4); 0.9962 (0.5); 0.9793 (0.5); 0.9530 (1.3); 0.9346 (2.5); 0.9220 (0.8); 0.9162 (1.2); 0.8801 (0.5); 0.8620 (0.4); 0.8446 (0.4); 0.0002 (12.3) 4.34.sup.[a] I- 020 [00066]
3.99.sup.[a] I- 021 [00067]
.sup.1H-NMR(400.2 MHz, d6-DMSO): = 9.3399 (2.0); 9.3210 (1.9); 8.0511 (0.3); 8.0351 (6.8); 7.5794 (2.6); 7.5577 (8.6); 7.5394 (8.5); 7.5185 (2.6); 7.3172 (4.4); 7.2976 (5.7); 7.1745 (5.4); 7.1551 (4.2); 5.7575 (1.4); 5.0861 (1.2); 5.0681 (1.9); 5.0502 (1.3); 5.0321 (0.3); 3.3592 (277.0); 3.2940 (0.5); 3.1696 (0.3); 2.6725 (0.7); 2.5037 (124.2); 2.3302 (0.8); 2.3102 (0.8); 2.2849 (16.0); 1.4668 (7.8); 1.4494 (7.8); 0.0002 (0.8) 4.13.sup.[a] I- 022 [00068]
4.77.sup.[a] I- 023 [00069]
3.55.sup.[a] I- 024 [00070]
4.13.sup.[a] I- 025 [00071]
3.85.sup.[a] I- 026 [00072]
.sup.1H-NMR(400.2 MHz, d6-DMSO): = 9.1453 (1.2); 9.1312 (2.5); 9.1171 (1.3); 7.8709 (11.8); 7.5789 (2.6); 7.5729 (1.4); 7.5634 (2.0); 7.5570 (15.7); 7.5467 (16.0); 7.5405 (2.5); 7.5309 (1.4); 7.5246 (2.8); 7.3934 (1.3); 7.3782 (2.2); 7.3742 (2.8); 7.3551 (1.6); 7.3178 (0.6); 7.3136 (0.6); 7.2992 (1.6); 7.2842 (1.4); 7.2793 (2.1); 7.2654 (1.2); 7.2612 (1.0); 7.1995 (2.2); 7.1757 (5.4); 7.1563 (4.8); 7.1407 (1.6); 7.1380 (1.6); 5.7589 (2.4); 3.5381 (1.7); 3.5209 (3.9); 3.5049 (3.9); 3.4876 (2.0); 3.3471 (222.0); 2.9207 (3.0); 2.9024 (5.5); 2.8845 (2.7); 2.6768 (0.6); 2.6726 (0.9); 2.6682 (0.7); 2.5258 (2.7); 2.5080 (112.7); 2.5035 (149.4); 2.4991 (108.7); 2.3348 (0.6); 2.3303 (0.9); 2.3260 (0.6); 0.0002 (2.7) 3.81.sup.[a] I- 027 [00073]
3.85.sup.[a] I- 028 [00074]
.sup.1H-NMR(400.2 MHz, d6-DMSO): = 8.9770 (0.4); 8.9627 (0.8); 8.9489 (0.4); 7.9235 (4.6); 7.5883 (1.5); 7.5828 (0.7); 7.5722 (1.0); 7.5666 (4.9); 7.5452 (4.9); 7.5396 (1.1); 7.5289 (0.6); 7.5234 (1.6); 7.0964 (16.0); 5.7565 (0.8); 3.4723 (0.4); 3.3911 (265.2); 3.3286 (0.4); 3.3208 (0.4); 3.2511 (0.3); 3.2355 (0.4); 3.2184 (0.6); 3.2025 (0.8); 3.1877 (0.5); 3.1624 (0.5); 3.1458 (0.7); 3.1297 (0.7); 3.1124 (0.3); 2.7229 (0.6); 2.7080 (0.6); 2.6894 (0.7); 2.6813 (0.4); 2.6742 (0.9); 2.5471 (0.3); 2.5303 (1.0); 2.5167 (20.4); 2.5126 (42.7); 2.5081 (56.8); 2.5037 (41.2); 2.4996 (20.1); 2.4018 (0.6); 2.3817 (0.7); 2.3685 (0.6); 2.3481 (0.6); 2.3348 (0.4); 2.2633 (9.9); 1.9895 (0.4); 1.9721 (0.4); 0.8797 (4.2); 0.8630 (4.1) 4.72.sup.[a] I- 029 [00075]
4.98.sup.[a] I- 030 [00076]
4.51.sup.[a] I- 031 [00077]
4.03.sup.[a] I- 032 [00078]
.sup.1H-NMR(400.2 MHz, d6-DMSO): = 8.8395 (0.8); 8.8194 (0.8); 7.9299 (4.9); 7.5769 (1.2); 7.5709 (1.4); 7.5620 (1.8); 7.5587 (0.9); 7.5529 (1.8); 7.4903 (0.6); 7.4809 (4.3); 7.4746 (3.3); 7.4692 (1.4); 7.4665 (1.7); 7.4642 (2.0); 7.4588 (0.5); 7.4557 (0.4); 7.1875 (14.0); 7.1677 (0.4); 5.7583 (1.1); 3.9664 (0.4); 3.9507 (0.5); 3.9346 (0.4); 3.3514 (100.4); 2.6773 (0.6); 2.6724 (0.5); 2.6633 (0.6); 2.6569 (0.6); 2.6504 (0.5); 2.6412 (0.5); 2.6323 (0.7); 2.6105 (0.6); 2.5257 (1.2); 2.5210 (1.8); 2.5123 (21.2); 2.5079 (43.3); 2.5033 (56.6); 2.4988 (39.6); 2.4943 (18.2); 2.4377 (16.0); 1.7879 (0.6); 1.7716 (0.8); 1.7575 (0.5); 1.7509 (0.6); 1.2003 (4.1); 1.1838 (4.1) 4.13.sup.[a] I- 033 [00079]
3.33.sup.[a] I- 034 [00080]
.sup.1H-NMR(400.2 MHz, d6-DMSO): = 9.0375 (0.5); 9.0244 (1.1); 9.0104 (0.6); 7.8530 (5.5); 7.5808 (1.2); 7.5757 (0.7); 7.5660 (0.9); 7.5596 (6.5); 7.5481 (6.7); 7.5324 (0.6); 7.5260 (1.4); 6.9128 (1.8); 6.8908 (2.5); 6.8151 (1.8); 6.8076 (2.5); 6.7799 (1.6); 6.7722 (1.1); 6.7580 (1.2); 6.7503 (0.9); 5.7586 (1.0); 3.7491 (14.1); 3.6811 (16.0); 3.4876 (0.7); 3.4710 (1.6); 3.4543 (1.6); 3.4379 (0.8); 3.3775 (0.4); 3.3494 (126.5); 2.8270 (1.4); 2.8089 (2.4); 2.7911 (1.3); 2.6723 (0.4); 2.5256 (1.0); 2.5076 (46.3); 2.5033 (62.8); 2.4988 (47.1); 2.3300 (0.4); 0.0002 (1.0) 3.81.sup.[a] I- 035 [00081]
5.24.sup.[a] I- 036 [00082]
.sup.1H-NMR(400.1 MHz, CDCl3): = 8.7408 (4.7); 8.0699 (1.3); 8.0489 (1.5); 7.7920 (1.2); 7.7902 (1.2); 7.7710 (1.5); 7.7693 (1.4); 7.7424 (1.0); 7.7391 (0.8); 7.7250 (1.2); 7.7215 (1.4); 7.7180 (0.7); 7.7040 (0.9); 7.7005 (0.7); 7.5812 (1.0); 7.5783 (0.9); 7.5637 (1.0); 7.5607 (1.4); 7.5430 (0.7); 7.5401 (0.6); 7.2600 (12.2); 7.2338 (1.2); 7.2239 (0.4); 7.2134 (2.5); 7.2063 (0.3); 7.2000 (0.4); 7.1927 (1.4); 7.0567 (1.5); 7.0376 (1.9); 6.9780 (2.0); 6.8963 (2.8); 6.8941 (2.8); 6.8916 (2.6); 6.8866 (2.5); 6.8808 (3.5); 6.8781 (2.5); 6.8251 (1.2); 6.8229 (1.1); 6.8189 (1.0); 6.8044 (1.0); 6.8020 (0.9); 6.7985 (0.9); 5.8903 (0.4); 5.8748 (0.8); 5.8606 (0.4); 5.2986 (7.1); 3.8229 (0.9); 3.8054 (2.1); 3.7900 (2.2); 4.11.sup.[a] 3.7723 (1.1); 3.7515 (16.0); 3.7292 (0.9); 2.9524 (1.6); 2.9346 (2.9); 2.9168 (1.5); 2.3162 (10.2); 2.2716 (9.5); 2.2546 (0.7); 2.0435 (1.2); 2.0048 (0.6); 1.9652 (0.5); 1.5698 (10.8); 1.4272 (0.9); 1.3715 (0.6); 1.3333 (0.5); 1.2856 (1.3); 1.2762 (0.7); 1.2582 (1.9); 1.2408 (0.6); 0.8806 (0.3); 0.0698 (4.7); 0.0080 (0.6); 0.0002 (14.5); 0.0083 (0.7) I- 037 [00083]
3.72.sup.[a] I- 038 [00084]
.sup.1H-NMR(400.2 MHz, d6-DMSO): = 9.0481 (1.2); 9.0348 (2.5); 9.0209 (1.3); 7.8604 (10.1); 7.5734 (1.9); 7.5683 (1.3); 7.5591 (1.6); 7.5524 (14.1); 7.5446 (16.0); 7.5292 (1.2); 7.5222 (2.1); 7.1886 (5.8); 7.1673 (7.0); 6.8613 (7.0); 6.8399 (6.8); 5.7557 (1.4); 3.9880 (2.0); 3.9706 (6.6); 3.9532 (6.7); 3.9357 (2.1); 3.4854 (1.8); 3.4675 (3.8); 3.4508 (4.0); 3.4350 (2.5); 3.3764 (485.6); 3.3069 (0.6); 3.2760 (0.4); 2.8006 (2.9); 2.7820 (5.2); 2.7642 (2.7); 2.6787 (0.6); 2.6743 (0.8); 2.6703 (0.7); 2.5275 (2.2); 2.5228 (3.6); 2.5096 (98.8); 2.5053 (140.3); 2.5010 (116.9); 2.3362 (0.6); 2.3321 (0.8); 2.3279 (0.7); 1.3085 (6.8); 1.2912 (14.0); 1.2737 (6.7); 0.0002 (2.4) 4.03.sup.[a] I- 039 [00085]
4.03.sup.[a] I- 040 [00086]
3.68.sup.[a] I- 041 [00087]
.sup.1H-NMR(400.1 MHz, CDCl3): = 8.4484 (1.7); 8.0283 (4.9); 7.8688 (3.8); 7.7985 (2.0); 7.7796 (2.4); 7.7420 (1.8); 7.7226 (2.4); 7.7113 (1.2); 7.6209 (1.6); 7.6015 (2.4); 7.5823 (1.0); 7.4142 (2.4); 7.3947 (2.8); 7.2629 (0.8); 7.0725 (5.2); 7.0475 (2.1); 5.2910 (2.6); 4.1877 (1.2); 4.1720 (1.3); 4.1500 (2.5); 4.1344 (2.5); 4.1123 (1.4); 4.0967 (1.3); 2.6909 (16.0); 2.5218 (10.6); 2.3375 (13.6); 1.6828 (0.6); 1.2604 (1.3); 0.0002 (0.8) 5.13.sup.[a] I- 042 [00088]
5.71.sup.[a] I- 043 [00089]
4.77.sup.[a] I- 044 [00090]
4.13.sup.[a] I- 045 [00091]
.sup.1H-NMR(400.2 MHz, d6-DMSO): = 9.2682 (3.4); 9.2575 (3.5); 8.0663 (0.4); 8.0241 (16.0); 7.6038 (0.7); 7.5981 (6.2); 7.5933 (2.9); 7.5822 (3.3); 7.5767 (15.8); 7.5521 (2.4); 7.5467 (15.9); 7.5416 (4.6); 7.5307 (3.2); 7.5251 (6.8); 7.3179 (3.1); 7.2995 (8.2); 7.2806 (6.4); 7.2129 (2.8); 7.2103 (2.6); 7.1945 (4.6); 7.1860 (7.5); 7.1828 (8.6); 7.1651 (6.6); 5.7562 (2.3); 3.7089 (0.4); 3.3683 (553.4); 3.2705 (0.4); 3.1755 (1.3); 3.1631 (1.4); 3.0694 (0.8); 3.0583 (1.8); 3.0495 (2.4); 3.0389 (2.5); 3.0304 (1.9); 3.0191 (0.9); 2.6782 (0.8); 2.6737 (1.2); 2.6693 (0.9); 2.5269 (3.3); 2.5221 (5.2); 2.5131 (66.6); 2.5091 (141.0); 2.5047 (191.3); 2.5002 (143.9); 2.3357 (0.8); 2.3314 (1.2); 2.3271 (0.9); 2.1744 (1.2); 2.1658 (1.3); 2.1582 (1.6); 2.1504 (2.6); 2.1427 (1.6); 2.1349 (1.5); 2.1264 (1.4); 1.3564 (1.0); 1.3427 (2.6); 1.3308 (2.4); 1.3204 (4.1); 1.3056 (4.2); 3.90.sup.[a] 1.2860 (2.9); 1.2717 (1.0); 0.0002 (9.9) I- 046 [00092]
3.72.sup.[a] I- 047 [00093]
5.44.sup.[a] I- 048 [00094]
.sup.1H-NMR(400.2 MHz, d6-DMSO): = 9.3271 (1.8); 9.3077 (1.8); 8.0110 (0.5); 7.9946 (8.8); 7.5616 (2.1); 7.5561 (3.0); 7.5467 (3.6); 7.5375 (4.2); 7.4767 (7.8); 7.4715 (7.4); 7.4632 (4.2); 7.4601 (4.1); 7.4504 (1.0); 7.3236 (4.3); 7.3036 (5.8); 7.2486 (0.4); 7.1758 (5.2); 7.1561 (4.0); 5.7569 (2.2); 5.0905 (1.2); 5.0724 (1.8); 5.0545 (1.2); 3.4213 (0.4); 3.4076 (0.6); 3.3594 (286.9); 3.3043 (0.3); 2.6727 (0.6); 2.6685 (0.5); 2.5079 (75.8); 2.5037 (101.5); 2.4994 (79.7); 2.3304 (0.6); 2.3097 (1.0); 2.2850 (16.0); 1.4675 (8.1); 1.4500 (8.2); 0.0002 (1.1) 3.63.sup.[a] I- 049 [00095]
3.25.sup.[a] I- 050 [00096]
.sup.1H-NMR(400.1 MHz, CDCl3): = 7.7992 (4.0); 7.7542 (2.2); 7.7348 (2.4); 7.6158 (1.9); 7.5963 (2.5); 7.5027 (1.9); 7.4831 (3.0); 7.4637 (1.3); 7.4008 (3.2); 7.3808 (3.7); 7.3577 (0.4); 7.2604 (20.0); 7.0831 (4.3); 7.0580 (2.5); 7.0386 (2.3); 6.2110 (1.0); 6.1962 (1.8); 6.1814 (1.0); 5.2987 (7.5); 4.2273 (1.6); 4.2116 (1.6); 4.1903 (3.4); 4.1747 (3.3); 4.1532 (1.8); 4.1375 (1.7); 4.1280 (0.4); 3.1201 (0.5); 3.1031 (0.3); 3.0842 (3.0); 3.0681 (5.8); 3.0519 (3.2); 2.7955 (1.0); 2.6160 (3.0); 2.5999 (5.9); 2.5839 (3.1); 2.5139 (11.6); 2.4493 (0.4); 2.3444 (1.7); 2.3280 (16.0); 2.0423 (0.9); 2.0047 (0.9); 1.9119 (0.9); 1.8963 (2.2); 1.8825 (3.0); 1.8737 (2.2); 1.8673 (2.9); 1.8576 (1.0); 1.8513 (1.1); 1.7772 (1.2); 1.7616 (3.0); 1.7550 (2.3); 1.7465 (3.1); 1.7327 (2.1); 1.7168 (0.8); 1.5628 (34.6); 1.2854 (0.7); 1.2756 (0.6); 1.2578 (1.5); 1.2402 (0.5); 0.8808 (0.4); 4.53.sup.[a] 0.0696 (6.2); 0.0002 (23.1); 0.0082 (1.4) I- 051 [00097]
.sup.1H-NMR(400.1 MHz, CDCl3): = 8.9049 (0.5); 8.7310 (7.2); 8.0817 (1.9); 8.0609 (2.4); 7.7794 (2.2); 7.7735 (1.7); 7.7701 (1.3); 7.7590 (3.5); 7.7562 (3.4); 7.7525 (2.1); 7.7491 (1.4); 7.7397 (0.7); 7.7350 (1.6); 7.7316 (1.2); 7.7216 (0.5); 7.6243 (2.9); 7.6001 (1.6); 7.5973 (1.5); 7.5799 (2.3); 7.5765 (1.4); 7.5619 (1.2); 7.5590 (1.0); 7.5182 (1.4); 7.4985 (1.9); 7.4440 (1.0); 7.4241 (2.7); 7.4115 (2.4); 7.3930 (2.1); 7.3733 (0.7); 7.2596 (9.4); 7.0611 (2.3); 7.0420 (2.8); 6.9780 (2.8); 6.8891 (1.8); 6.8680 (1.5); 5.9447 (0.7); 5.9303 (1.2); 5.9163 (0.7); 5.2972 (16.0); 3.8430 (1.4); 3.8255 (3.5); 3.8102 (3.6); 3.7928 (1.6); 3.0053 (0.4); 2.9751 (2.3); 2.9576 (4.5); 2.9400 (2.2); 2.3535 (1.2); 2.3138 (15.3); 2.2906 (1.6); 2.2667 (14.3); 2.0393 (0.4); 1.9654 (0.7); 1.5865 (16.1); 1.2859 (0.4); 1.2737 (0.4); 1.2558 (0.8); 0.8817 (0.4); 0.0708 (2.9); 0.0078 4.74.sup.[a] (0.5); 0.0002 (10.6); 0.0084 (0.6) I- 052 [00098]
4.32.sup.[a] I- 053 [00099]
4.08.sup.[a] I- 054 [00100]
4.03.sup.[a] I- 055 [00101]
.sup.1H-NMR(400.2 MHz, d6-DMSO): = 9.4003 (3.0); 9.3815 (3.0); 8.0377 (14.4); 7.5717 (0.4); 7.5624 (3.7); 7.5569 (5.1); 7.5472 (5.7); 7.5382 (7.1); 7.5258 (0.6); 7.4974 (0.4); 7.4869 (2.1); 7.4778 (15.8); 7.4730 (14.1); 7.4645 (7.1); 7.4609 (8.8); 7.4545 (15.8); 7.4333 (16.0); 7.4280 (3.7); 7.4171 (2.0); 7.4117 (5.4); 5.7589 (3.7); 5.1329 (0.5); 5.1154 (2.1); 5.0975 (3.2); 5.0794 (2.1); 5.0619 (0.5); 3.7078 (0.3); 3.3493 (281.3); 3.1749 (0.4); 3.1620 (0.4); 2.6766 (0.7); 2.6722 (1.0); 2.6677 (0.8); 2.5255 (3.0); 2.5077 (127.5); 2.5033 (171.3); 2.4988 (125.8); 2.3346 (0.7); 2.3299 (1.0); 2.3257 (0.8); 1.4736 (14.1); 1.4561 (14.1); 0.0002 (2.6) 3.72.sup.[a] I- 056 [00102]
4.18.sup.[a] I- 057 [00103]
4.37.sup.[a] I- 058 [00104]
3.72.sup.[a] I- 059 [00105]
2.8.sup.[a] I- 060 [00106]
.sup.1H-NMR(400.2 MHz, d6-DMSO): = 9.4138 (2.8); 9.3951 (2.8); 8.0736 (16.0); 7.5811 (4.3); 7.5754 (2.1); 7.5650 (2.9); 7.5590 (15.9); 7.5409 (15.7); 7.5352 (3.3); 7.5248 (1.9); 7.5190 (4.6); 7.4704 (4.0); 7.4654 (1.9); 7.4551 (3.7); 7.4488 (13.8); 7.4311 (15.0); 7.4255 (3.2); 7.4151 (1.8); 7.4094 (4.4); 7.4011 (2.2); 5.7574 (3.5); 5.1282 (0.4); 5.1106 (1.8); 5.0927 (2.8); 5.0747 (1.9); 5.0571 (0.4); 3.4490 (0.4); 3.3599 (468.2); 3.1688 (0.6); 2.6774 (0.8); 2.6731 (1.1); 2.6686 (0.8); 2.5434 (1.2); 2.5264 (3.1); 2.5218 (4.6); 2.5127 (64.6); 2.5085 (138.4); 2.5041 (187.7); 2.4996 (139.0); 2.4954 (69.6); 2.3353 (0.8); 2.3308 (1.1); 2.3265 (0.8); 1.4731 (12.3); 1.4556 (12.4); 1.4114 (0.5); 1.3937 (0.5); 0.0002 (1.0) 4.18.sup.[a] I- 061 [00107]
.sup.1H-NMR(400.2 MHz, d6-DMSO): = 9.0200 (1.2); 9.0059 (2.6); 8.9915 (1.3); 7.9577 (11.9); 7.5883 (9.2); 7.5721 (3.7); 7.5666 (15.6); 7.5610 (6.9); 7.5520 (12.9); 7.5439 (16.0); 7.5383 (4.4); 7.5275 (2.3); 7.5222 (5.3); 7.4671 (1.1); 5.7568 (2.7); 3.4650 (0.8); 3.3929 (683.2); 3.3895 (721.1); 3.2989 (0.8); 3.2858 (0.8); 3.2658 (1.0); 3.2502 (1.1); 3.2326 (1.9); 3.2168 (2.8); 3.2074 (2.0); 3.2020 (2.0); 3.1917 (2.6); 3.1753 (2.1); 3.1583 (0.9); 3.1430 (0.7); 2.8975 (1.6); 2.8829 (1.7); 2.8640 (1.9); 2.8495 (2.0); 2.6817 (0.8); 2.6771 (1.1); 2.6728 (0.8); 2.5571 (1.9); 2.5472 (1.4); 2.5361 (2.5); 2.5304 (3.7); 2.5168 (68.9); 2.5126 (143.8); 2.5082 (191.2); 2.5037 (139.1); 2.4997 (67.7); 2.4463 (0.3); 2.3394 (0.9); 2.3348 (1.2); 2.3305 (0.9); 2.0863 (0.4); 2.0696 (0.8); 2.0532 (1.3); 4.77.sup.[a] 2.0345 (1.2); 2.0177 (0.8); 2.0009 (0.4); 1.2353 (0.4); 0.8901 (11.7); 0.8734 (11.5); 0.8419 (0.4); 0.8252 (0.4) I- 062 [00108]
.sup.1H-NMR(400.2 MHz, d6-DMSO): = 9.0168 (0.6); 9.0035 (1.1); 8.9897 (0.6); 7.8164 (6.1); 7.5635 (1.3); 7.5578 (1.7); 7.5487 (2.2); 7.5395 (2.4); 7.4910 (0.7); 7.4818 (5.0); 7.4760 (4.1); 7.4677 (2.2); 7.4652 (2.3); 7.4557 (0.5); 6.9148 (1.9); 6.8927 (2.6); 6.8229 (1.9); 6.8153 (2.5); 6.7817 (1.6); 6.7740 (1.2); 6.7596 (1.2); 6.7520 (0.9); 5.7593 (1.7); 3.7523 (14.2); 3.6834 (16.0); 3.4895 (0.7); 3.4727 (1.6); 3.4565 (1.7); 3.4395 (0.8); 3.3859 (0.3); 3.3426 (140.6); 2.8306 (1.4); 2.8124 (2.5); 2.7948 (1.3); 2.6761 (0.3); 2.6719 (0.4); 2.5251 (1.4); 2.5073 (57.0); 2.5029 (75.0); 2.4985 (54.7); 2.3295 (0.4); 0.0002 (1.7) 3.29.sup.[a] I- 063 [00109]
3.85.sup.[a] I- 064 [00110]
4.46.sup.[a] I- 065 [00111]
3.63.sup.[a] I- 066 [00112]
.sup.1H-NMR(400.2 MHz, d6-DMSO): = 9.0262 (1.2); 9.0126 (2.4); 8.9986 (1.2); 7.8285 (13.6); 7.5564 (2.7); 7.5507 (3.8); 7.5414 (4.6); 7.5322 (5.4); 7.5201 (0.5); 7.4897 (1.5); 7.4806 (10.5); 7.4750 (9.2); 7.4668 (4.7); 7.4637 (4.9); 7.4544 (1.1); 7.1942 (6.3); 7.1728 (7.4); 6.8704 (0.8); 6.8632 (7.8); 6.8417 (7.2); 5.7589 (3.3); 3.9899 (2.2); 3.9725 (7.4); 3.9550 (7.5); 3.9376 (2.3); 3.4861 (1.5); 3.4689 (3.3); 3.4517 (3.4); 3.4356 (1.8); 3.3461 (252.6); 3.3079 (0.5); 2.8046 (2.9); 2.7860 (5.0); 2.7680 (2.7); 2.6765 (0.6); 2.6720 (0.8); 2.6676 (0.7); 2.5253 (2.6); 2.5207 (3.7); 2.5116 (46.5); 2.5074 (100.2); 2.5030 (136.3); 2.4985 (103.0); 2.4943 (52.2); 2.3344 (0.5); 2.3298 (0.8); 2.3254 (0.6); 1.3087 (7.7); 1.2913 (16.0); 1.2738 (7.5); 0.0002 (1.4) 3.55.sup.[a] I- 067 [00113]
3.25.sup.[a] I- 068 [00114]
4.23.sup.[a] I- 069 [00115]
3.29.sup.[a] I- 070 [00116]
.sup.1H-NMR(400.2 MHz, d6-DMSO): = 8.8394 (1.1); 8.8192 (1.1); 7.9391 (5.3); 7.5948 (2.1); 7.5900 (1.0); 7.5786 (1.2); 7.5733 (5.6); 7.5461 (5.5); 7.5296 (0.9); 7.5245 (2.2); 7.1555 (2.9); 7.1341 (3.4); 6.8497 (3.6); 6.8282 (3.3); 5.7568 (1.1); 3.9619 (0.5); 3.9454 (0.6); 3.9278 (0.5); 3.7090 (16.0); 3.4219 (0.3); 3.3633 (237.9); 2.6732 (0.6); 2.6375 (0.6); 2.6154 (1.1); 2.5982 (1.2); 2.5762 (0.6); 2.5264 (1.3); 2.5086 (54.1); 2.5042 (72.7); 2.4999 (55.5); 2.3312 (0.4); 1.7984 (0.4); 1.7778 (0.8); 1.7564 (1.0); 1.7402 (0.8); 1.7190 (0.4); 1.1939 (5.1); 1.1774 (5.1); 0.0002 (0.4) 4.18.sup.[a] I- 071 [00117]
.sup.1H-NMR(400.2 MHz, d6-DMSO): = 9.0117 (1.6); 8.9982 (3.2); 8.9847 (1.7); 7.9587 (15.1); 7.5921 (5.8); 7.5872 (3.2); 7.5759 (3.4); 7.5705 (15.8); 7.5435 (16.0); 7.5271 (2.5); 7.5218 (6.1); 7.3135 (2.6); 7.2947 (8.0); 7.2769 (8.0); 7.2541 (11.2); 7.2371 (4.8); 7.2041 (2.8); 7.1864 (4.1); 7.1689 (1.6); 5.7591 (3.5); 3.4086 (0.4); 3.3915 (0.4); 3.3443 (328.2); 3.3077 (2.9); 3.2908 (5.9); 3.2761 (5.8); 3.2593 (2.5); 3.1738 (0.5); 3.1628 (0.5); 2.6972 (4.1); 2.6775 (7.2); 2.6591 (4.7); 2.5253 (3.3); 2.5074 (140.7); 2.5031 (193.5); 2.4989 (155.3); 2.3342 (0.8); 2.3299 (1.1); 2.3256 (0.9); 2.2841 (0.4); 1.8782 (1.2); 1.8600 (3.7); 1.8410 (5.0); 1.8226 (3.7); 1.8051 (1.1); 0.0002 (1.1) 4.03.sup.[a] I- 072 [00118]
.sup.1H-NMR(400.2 MHz, d6-DMSO): = 9.3399 (1.5); 9.3204 (1.6); 8.0135 (8.4); 7.5632 (1.9); 7.5576 (2.6); 7.5484 (3.3); 7.5391 (3.6); 7.4773 (7.2); 7.4719 (6.3); 7.4632 (3.5); 7.4608 (3.5); 7.4514 (0.9); 7.2682 (0.8); 7.2485 (5.5); 7.2313 (3.8); 7.2259 (3.1); 7.2064 (0.8); 7.0854 (1.9); 7.0675 (1.4); 5.7588 (2.0); 5.0895 (1.1); 5.0715 (1.6); 5.0531 (1.1); 3.3468 (111.1); 3.1748 (0.4); 3.1620 (0.4); 2.6718 (0.6); 2.5249 (1.9); 2.5071 (72.2); 2.5029 (94.4); 2.4990 (73.5); 2.3337 (0.5); 2.3296 (0.7); 2.3258 (0.6); 2.3100 (16.0); 2.2944 (0.7); 2.2246 (0.4); 1.4766 (7.4); 1.4592 (7.4); 0.0002 (1.2) 3.63.sup.[a] I- 073 [00119]
3.25.sup.[a] I- 074 [00120]
.sup.1H-NMR(400.1 MHz, CDCl3): = 8.0339 (1.2); 7.8606 (3.1); 7.8012 (1.7); 7.7822 (2.0); 7.7040 (1.5); 7.6845 (2.0); 7.5821 (1.5); 7.5626 (2.2); 7.5430 (0.9); 7.2594 (4.7); 7.0876 (2.0); 7.0685 (3.1); 7.0484 (0.7); 7.0301 (3.4); 6.9976 (2.2); 6.9794 (1.6); 3.7213 (1.3); 3.7043 (3.0); 3.6859 (3.0); 3.6692 (1.5); 2.9674 (2.4); 2.9487 (4.0); 2.9304 (2.5); 2.9065 (2.3); 2.8042 (16.0); 2.3599 (14.0); 2.3429 (2.5); 2.3127 (13.4); 1.5626 (3.6); 1.2846 (0.5); 1.2551 (0.9); 0.0707 (1.2); 0.0002 (5.3) 5.21.sup.[a] I- 075 [00121]
.sup.1H-NMR(400.2 MHz, d6-DMSO): = 8.8487 (0.8); 8.8279 (0.8); 7.9604 (4.5); 7.5950 (1.7); 7.5896 (0.7); 7.5789 (1.0); 7.5733 (4.6); 7.5680 (0.8); 7.5515 (0.8); 7.5461 (4.6); 7.5408 (1.2); 7.5299 (0.7); 7.5244 (1.8); 7.4707 (0.8); 7.1848 (16.0); 7.1666 (0.5); 5.7589 (1.5); 3.9622 (0.3); 3.9455 (0.4); 3.9299 (0.4); 3.3470 (79.9); 2.6767 (0.4); 2.6721 (0.6); 2.6676 (0.8); 2.6512 (0.5); 2.6445 (0.7); 2.6249 (0.7); 2.6029 (0.5); 2.5425 (0.4); 2.5255 (1.4); 2.5121 (27.3); 2.5077 (56.4); 2.5032 (74.2); 2.4986 (52.4); 2.4942 (24.4); 2.4635 (0.7); 2.4374 (15.0); 2.3300 (0.4); 1.7867 (0.6); 1.7709 (0.8); 1.7509 (0.6); 1.7333 (0.3); 1.1966 (3.9); 1.1801 (3.9) 4.61.sup.[a] I- 076 [00122]
.sup.1H-NMR(400.1 MHz, CDCl3): = 8.0292 (0.7); 7.4171 (2.3); 7.3900 (1.6); 7.3367 (1.2); 7.3178 (2.2); 7.2989 (1.2); 7.2592 (7.2); 7.2474 (1.7); 7.2280 (1.1); 7.0896 (1.6); 7.0705 (2.3); 7.0258 (2.2); 6.9958 (1.5); 6.9770 (1.0); 5.2980 (2.6); 3.7101 (1.0); 3.6937 (2.1); 3.6734 (2.1); 3.6576 (1.2); 2.9620 (1.7); 2.9430 (2.7); 2.9249 (1.7); 2.7819 (16.0); 2.3675 (11.6); 2.3587 (12.4); 2.3112 (10.7); 1.5557 (10.7); 1.2853 (0.4); 1.2547 (0.6); 0.0699 (1.7); 0.0075 (0.5); 0.0002 (8.4); 0.0079 (0.5) 4.89.sup.[a] I- 077 [00123]
4.03.sup.[a] I- 078 [00124]
4.23.sup.[a] I- 079 [00125]
.sup.1H-NMR(400.2 MHz, d6-DMSO): = 9.4782 (3.4); 9.4596 (3.5); 8.0583 (16.0); 7.9505 (0.4); 7.8092 (6.4); 7.7708 (3.0); 7.7532 (4.0); 7.7174 (0.3); 7.7009 (0.4); 7.6541 (1.5); 7.6311 (9.1); 7.6131 (4.5); 7.5940 (1.4); 7.5673 (0.4); 7.5603 (0.6); 7.5513 (3.8); 7.5456 (5.5); 7.5363 (6.7); 7.5270 (8.3); 7.5152 (1.1); 7.4990 (0.6); 7.4885 (2.3); 7.4797 (15.3); 7.4742 (14.2); 7.4662 (8.0); 7.4629 (7.7); 7.4534 (2.3); 7.4393 (0.7); 7.4244 (0.7); 7.4204 (0.9); 7.4126 (0.6); 7.3990 (0.9); 7.3932 (0.7); 7.3849 (0.8); 7.3809 (0.8); 6.9970 (0.5); 6.9912 (0.5); 5.7562 (5.2); 5.2359 (0.5); 5.2189 (2.2); 5.2010 (3.5); 5.1832 (2.4); 5.1654 (0.6); 3.4776 (0.5); 3.4630 (0.8); 3.4479 (1.1); 3.3753 (891.2); 3.2419 (0.5); 3.2213 (0.4); 3.2054 (0.4); 3.1751 (0.5); 3.1645 (0.6); 2.6788 (1.2); 2.6743 (1.6); 2.6699 (1.3); 2.5445 (1.8); 2.5275 (5.0); 2.5097 (209.4); 2.5053 (287.9); 2.5009 (227.0); 2.4531 (0.6); 2.4481 (0.6); 2.4423 (0.5); 2.3365 (1.2); 2.3321 (1.7); 2.3277 (1.4); 1.8417 (0.6); 1.5141 (15.4); 1.4966 (15.5); 1.4581 (1.2); 1.4485 (0.6); 1.4408 (1.1); 0.0002 (0.9) 3.81.sup.[a] I- 080 [00126]
.sup.1H-NMR(400.1 MHz, CDCl3): = 8.0440 (0.3); 8.0310 (0.6); 8.0162 (0.4); 7.3628 (1.0); 7.3431 (1.8); 7.3230 (1.5); 7.2593 (6.2); 7.2064 (1.0); 7.2038 (1.4); 7.2005 (1.1); 7.1875 (0.8); 7.1839 (1.1); 7.1815 (0.9); 7.1570 (1.4); 7.1507 (1.7); 7.1469 (1.3); 7.0880 (1.3); 7.0689 (2.0); 7.0254 (1.8); 6.9911 (1.8); 6.9845 (1.1); 6.9822 (1.1); 6.9765 (0.9); 6.9703 (1.3); 6.9680 (1.0); 6.9637 (0.9); 6.9615 (0.8); 5.2977 (15.3); 3.7979 (16.0); 3.7100 (0.9); 3.6938 (1.7); 3.6760 (1.4); 3.6732 (1.7); 3.6574 (1.0); 2.9611 (1.4); 2.9420 (2.2); 2.9240 (1.4); 2.7876 (15.7); 2.3580 (9.8); 2.3108 (8.9); 1.5595 (7.2); 1.2545 (0.3); 0.0702 (2.0); - 0.0002 (7.6) 4.59.sup.[a] I- 081 [00127]
.sup.1H-NMR(300.2 MHz, CDCl3): = 8.2467 (5.7); 7.6064 (3.1); 7.5793 (0.4); 7.5186 (6.3); 7.4966 (2.1); 7.4844 (0.7); 7.4703 (4.0); 7.4495 (0.4); 7.4435 (0.5); 7.2990 (3.0); 7.0649 (1.7); 7.0386 (4.7); 6.9886 (1.8); 6.9629 (1.0); 6.4867 (0.8); 3.6807 (1.3); 3.6574 (3.1); 3.6373 (3.2); 3.6141 (1.5); 2.9113 (2.3); 2.8878 (4.4); 2.8642 (2.1); 2.3295 (16.0); 2.3200 (15.2); 1.6422 (1.0); 0.0391 (3.6) 4.93.sup.[a] I- 082 [00128]
.sup.1H-NMR(300.2 MHz, CDCl3): = 7.8669 (1.0); 7.8222 (0.5); 7.7953 (0.6); 7.7541 (0.5); 7.7277 (0.6); 7.6573 (0.9); 7.6292 (1.6); 7.6051 (0.9); 7.5711 (0.8); 7.5647 (1.0); 7.5334 (3.0); 7.4144 (0.6); 7.4077 (0.6); 7.3862 (0.5); 7.3795 (0.5); 7.2987 (7.6); 7.2603 (0.4); 6.7483 (0.3); 5.3379 (0.4); 4.4477 (0.5); 4.4267 (0.5); 4.3989 (1.0); 4.3779 (1.0); 4.3500 (0.6); 4.3290 (0.5); 1.6038 (16.0); 0.1066 (0.4); 0.0366 (7.6) 4.81.sup.[a] I- 083 [00129]
.sup.1H-NMR(400.2 MHz, d6-DMSO): = 9.4841 (2.0); 9.4654 (2.0); 8.0981 (10.6); 7.8003 (3.7); 7.7666 (1.7); 7.7488 (2.3); 7.6538 (0.9); 7.6343 (3.9); 7.6299 (4.6); 7.6115 (2.4); 7.5924 (0.8); 7.5709 (1.3); 7.5635 (1.0); 7.5557 (1.3); 7.5485 (15.5); 7.5436 (16.0); 7.5286 (0.9); 7.5210 (1.4); 5.7578 (2.5); 5.2158 (1.3); 5.1980 (2.0); 5.1802 (1.3); 5.1625 (0.3); 3.3594 (287.7); 2.6779 (0.6); 2.6734 (0.8); 2.6690 (0.6); 2.5438 (0.3); 2.5267 (2.3); 2.5088 (102.0); 2.5044 (134.2); 2.5001 (98.9); 2.3356 (0.6); 2.3312 (0.8); 2.3269 (0.6); 2.3105 (0.3); 1.5136 (8.8); 1.4960 (8.8); 1.4768 (0.3); 1.4583 (0.4); 0.0002 (1.4) 4.27.sup.[a] I- 084 [00130]
.sup.1H-NMR(400.2 MHz, d6-DMSO): = 9.0666 (0.8); 9.0529 (1.7); 9.0397 (0.9); 7.8645 (6.6); 7.5832 (1.9); 7.5618 (7.3); 7.5467 (7.7); 7.5252 (2.0); 7.2424 (0.9); 7.2227 (2.0); 7.2090 (2.2); 7.1939 (2.2); 6.9958 (2.5); 6.9755 (2.1); 6.9113 (1.4); 6.8929 (2.4); 6.8743 (1.2); 5.7561 (1.0); 3.8037 (16.0); 3.4881 (1.1); 3.4708 (2.6); 3.4532 (2.6); 3.4375 (1.7); 3.3701 (340.5); 3.3262 (1.1); 3.2877 (0.4); 2.8577 (2.1); 2.8388 (3.4); 2.8209 (1.9); 2.6731 (0.6); 2.5042 (94.1); 2.3302 (0.6) 3.90.sup.[a] I- 085 [00131]
.sup.1H-NMR(400.2 MHz, d6-DMSO): = 9.4873 (1.8); 9.4688 (1.8); 8.0955 (7.6); 7.7996 (3.4); 7.7660 (1.6); 7.7482 (2.1); 7.6543 (0.8); 7.6348 (3.7); 7.6302 (4.4); 7.6120 (2.3); 7.5927 (0.7); 7.5711 (1.2); 7.5638 (0.8); 7.5560 (1.2); 7.5487 (15.5); 7.5439 (16.0); 7.5366 (1.2); 7.5290 (0.8); 7.5212 (1.2); 5.7562 (1.3); 5.2145 (1.2); 5.1969 (1.8); 5.1788 (1.2); 3.4601 (0.6); 3.3912 (124.3); 3.3766 (271.2); 3.3738 (270.0); 3.3148 (0.5); 2.6793 (0.6); 2.6747 (0.8); 2.6702 (0.6); 2.5442 (0.4); 2.5281 (2.6); 2.5233 (4.0); 2.5147 (47.8); 2.5103 (99.1); 2.5058 (130.6); 2.5012 (91.9); 2.4967 (42.5); 2.3370 (0.6); 2.3325 (0.8); 2.3279 (0.6); 1.5137 (8.7); 1.4961 (8.6) 4.27.sup.[a] I- 086 [00132]
4.41.sup.[a] I- 087 [00133]
.sup.1H-NMR(400.2 MHz, d6-DMSO): = 8.8334 (1.0); 8.8133 (1.0); 7.9137 (6.0); 7.5809 (1.3); 7.5749 (1.6); 7.5660 (2.1); 7.5569 (2.1); 7.4942 (0.6); 7.4848 (4.7); 7.4786 (3.7); 7.4683 (2.2); 7.4597 (0.5); 7.1639 (2.7); 7.1425 (3.1); 6.8617 (0.4); 6.8545 (3.4); 6.8329 (3.0); 5.7608 (1.1); 3.9693 (0.4); 3.9531 (0.6); 3.9376 (0.4); 3.7134 (16.0); 3.3621 (141.2); 3.3251 (0.4); 2.6814 (0.4); 2.6768 (0.5); 2.6728 (0.5); 2.6535 (0.5); 2.6375 (0.6); 2.6297 (0.8); 2.6090 (0.8); 2.5876 (0.6); 2.5471 (0.4); 2.5302 (1.4); 2.5254 (2.1); 2.5165 (25.1); 2.5123 (51.6); 2.5079 (67.9); 2.5034 (48.9); 2.3346 (0.4); 1.8016 (0.4); 1.7794 (0.7); 1.7625 (0.9); 1.7439 (0.7); 1.7234 (0.4); 1.2016 (4.8); 1.1851 (4.7) 3.72.sup.[a] I- 088 [00134]
.sup.1H-NMR(400.1 MHz, CDCl3): = 8.2107 (4.8); 7.5224 (5.1); 7.2659 (1.7); 7.2608 (6.2); 7.2601 (6.5); 7.2482 (2.2); 7.2472 (2.2); 7.2278 (1.5); 7.0238 (1.6); 7.0046 (2.5); 6.9915 (2.4); 6.9475 (1.6); 6.9283 (1.0); 6.8630 (1.4); 6.8571 (2.6); 6.8539 (1.9); 6.8357 (2.8); 6.8295 (2.8); 6.8247 (2.3); 6.8194 (1.1); 6.5743 (0.7); 3.7942 (0.8); 3.7663 (16.0); 3.6280 (1.1); 3.6106 (2.3); 3.5954 (2.4); 3.5776 (1.2); 2.8499 (1.9); 2.8319 (3.3); 2.8139 (1.7); 2.2962 (12.1); 2.2841 (11.3); 1.5655 (5.7); 0.0705 (0.5); 0.0008 (7.0); 0.0002 (7.4); 0.0072 (0.4) 4.44.sup.[a] I- 089 [00135]
3.37.sup.[a] I- 090 [00136]
3.21.sup.[a] I- 091 [00137]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.5344 (0.7); 9.5187 (1.4); 9.5032 (0.7); 7.7237 (4.1); 7.7069 (1.9); 7.7017 (5.4); 7.4941 (3.6); 7.4743 (2.9); 7.4723 (2.8); 7.3790 (2.0); 7.3591 (2.4); 7.1477 (2.9); 7.1245 (1.6); 7.1047 (1.4); 4.0842 (0.7); 4.0676 (0.7); 4.0453 (1.6); 4.0289 (1.5); 4.0061 (0.8); 3.9896 (0.8); 3.3343 (31.2); 2.8962 (1.6); 2.7794 (16.0); 2.7369 (1.4); 2.5305 (0.7); 2.5127 (26.5); 2.5083 (35.0); 2.5040 (28.0); 2.4757 (7.6); 2.3349 (0.4); 2.2990 (10.1) 5.17.sup.[a] I- 092 [00138]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.2823 (0.8); 9.2670 (1.6); 9.2516 (0.8); 7.9586 (1.2); 7.6965 (6.0); 7.4011 (2.6); 7.3949 (7.8); 7.3931 (7.5); 7.3828 (5.6); 7.3769 (5.7); 7.3574 (3.1); 7.2955 (1.0); 7.2897 (0.9); 7.2770 (1.2); 7.2607 (0.6); 7.2544 (0.6); 7.1217 (3.1); 7.0815 (1.7); 7.0618 (1.5); 4.0767 (0.8); 4.0612 (0.8); 4.0394 (1.8); 4.0238 (1.8); 4.0018 (0.9); 3.9863 (0.9); 3.3351 (33.7); 2.8965 (7.9); 2.7375 (7.0); 2.5307 (0.6); 2.5129 (29.0); 2.5085 (39.6); 2.5041 (31.3); 2.4479 (8.2); 2.3354 (0.3); 2.2829 (16.0); 2.2669 (11.3) 4.77.sup.[a] I- 093 [00139]
.sup.1H-NMR(600.1 MHz, d.sub.6-DMSO): = 8.9222 (0.5); 8.9128 (1.0); 8.9034 (0.5); 8.3170 (0.9); 8.3031 (1.0); 8.2950 (1.6); 8.2164 (4.6); 8.1439 (0.8); 8.1309 (0.9); 7.9550 (0.8); 7.9209 (0.7); 7.9078 (1.3); 7.8947 (0.6); 7.3868 (0.3); 7.3825 (2.8); 7.3793 (1.0); 7.3719 (1.1); 7.3685 (4.5); 7.3643 (0.6); 7.3214 (0.5); 7.3173 (3.6); 7.3140 (1.0); 7.3064 (0.8); 7.3032 (2.4); 7.2990 (0.3); 3.5591 (0.7); 3.5474 (1.6); 3.5377 (1.6); 3.5261 (0.7); 3.3261 (34.0); 2.8924 (6.9); 2.8836 (0.1); 2.8740 3.53.sup.[a] (1.2); 2.8623 (2.4); 2.8506 (1.2); 2.7706 (16.0); 2.7336 (5.4); 2.7327 (5.4); 2.6190 (0.1); 2.6160 (0.2); 2.6129 (0.2); 2.6010 (12.4); 2.5250 (0.3); 2.5219 (0.4); 2.5188 (0.3); 2.5101 (6.7); 2.5070 (15.2); 2.5040 (21.6); 2.5009 (15.6); 2.4979 (7.2); 2.3879 (0.1); 0.0054 (0.2); 0.0001 (8.7); 0.0057 (0.3) I- 094 [00140]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.4071 (1.2); 9.3916 (2.5); 9.3760 (1.3); 8.6554 (9.0); 8.0392 (2.8); 8.0185 (3.4); 7.8330 (1.6); 7.8153 (2.8); 7.7975 (1.4); 7.7946 (1.6); 7.6163 (1.6); 7.5981 (2.7); 7.5781 (1.6); 7.4057 (3.3); 7.3857 (4.7); 7.3739 (12.5); 7.3676 (12.4); 7.3610 (9.9); 7.3455 (3.9); 7.3318 (1.8); 7.3252 (2.2); 7.3195 (1.6); 7.3100 (1.8); 7.3013 (0.9); 7.2970 (0.7); 7.1714 (4.4); 7.1019 (2.4); 7.0821 (2.1); 4.2009 (1.2); 3.3273 (57.3); 2.8897 (0.5); 2.7316 (0.4); 2.5057 (43.5); 2.5015 (62.4); 2.4974 (56.2); 2.3300 (16.0) 4.25.sup.[a] I- 095 [00141]
.sup.1H-NMR(600.1 MHz, d.sub.6-DMSO): = 8.8781 (0.4); 8.8687 (0.9); 8.8592 (0.4); 8.3189 (0.8); 8.3050 (1.0); 8.2970 (1.5); 8.2111 (4.2); 8.1451 (0.7); 8.1439 (0.7); 8.1321 (0.8); 8.1309 (0.8); 7.9546 (0.8); 7.9201 (0.7); 7.9070 (1.2); 7.8939 (0.6); 7.0817 (1.7); 7.0680 (1.8); 6.5608 (1.8); 6.5568 (2.0); 6.4862 (1.2); 6.4821 (1.1); 6.4725 (1.2); 6.4684 (1.1); 3.7932 (12.9); 3.7492 (16.0); 3.7297 (0.1); 3.4714 (0.5); 3.4599 (1.2); 3.4496 (1.2); 3.4380 (0.6); 3.3249 (32.1); 2.8918 (6.9); 2.7752 (1.2); 2.7682 (15.1); 2.7636 (2.2); 2.7515 (1.0); 2.7333 (5.4); 2.7324 (5.5); 3.28.sup.[a] 2.6443 (11.2); 2.6186 (0.1); 2.6155 (0.2); 2.6125 (0.1); 2.5246 (0.3); 2.5214 (0.3); 2.5183 (0.3); 2.5096 (6.2); 2.5065 (14.0); 2.5035 (19.9); 2.5004 (14.2); 2.4973 (6.4); 2.3873 (0.1); 0.0054 (0.2); 0.0001 (6.9); 0.0057 (0.2) I- 096 [00142]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.3954 (0.9); 9.3800 (2.0); 9.3644 (1.0); 8.6343 (7.8); 8.0341 (2.3); 8.0132 (2.8); 7.9520 (1.6); 7.8287 (1.2); 7.8256 (1.4); 7.8113 (1.7); 7.8081 (2.4); 7.8048 (1.6); 7.7904 (1.2); 7.7872 (1.4); 7.6154 (1.2); 7.6128 (1.3); 7.5949 (2.3); 7.5920 (2.0); 7.5773 (1.3); 7.5746 (1.4); 7.4063 (2.6); 7.3864 (3.0); 7.3668 (2.5); 7.3459 (2.1); 7.2694 (1.2); 7.2503 (3.1); 7.2312 (2.6); 7.2200 (3.7); 7.1724 (5.2); 7.1568 (1.7); 7.1409 (2.4); 7.1224 (1.7); 7.1001 (2.0); 7.0807 (1.7); 4.2015 (1.0); 3.3247 (39.6); 2.8893 (9.7); 2.7314 (8.3); 2.7303 (8.5); 2.5403 (0.7); 2.5052 (39.2); 2.5010 (54.8); 2.4968 (46.7); 2.3299 (13.0); 2.2580 (16.0) 4.58.sup.[a] I- 097 [00143]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.2585 (0.9); 9.2433 (1.8); 9.2280 (0.9); 7.8814 (7.0); 7.3740 (3.1); 7.3681 (8.4); 7.3636 (5.9); 7.3545 (3.7); 7.3429 (7.1); 7.2739 (5.5); 7.2539 (3.6); 7.2015 (0.4); 7.1137 (3.4); 7.0812 (1.8); 7.0616 (1.6); 4.0706 (0.9); 4.0554 (0.9); 4.0333 (2.0); 4.0177 (2.0); 3.9954 (1.0); 3.9800 (1.0); 3.3819 (5.7); 2.8910 (0.6); 2.7319 (0.5); 2.5252 (0.8); 2.5074 (31.1); 2.5030 (41.9); 2.4986 (32.0); 2.4418 (9.0); 2.3333 (16.0); 2.3023 (1.3); 2.2594 (12.4); 1.9688 (0.8); 0.9180 (0.5) 4.84.sup.[a] I- 098 [00144]
.sup.1H-NMR(600.1 MHz, d.sub.6-DMSO): = 9.5308 (0.5); 9.5204 (1.0); 9.5100 (0.5); 8.3328 (0.9); 8.3190 (1.0); 8.3089 (1.6); 8.2444 (0.1); 8.2357 (4.6); 8.1533 (0.8); 8.1521 (0.8); 8.1402 (0.8); 8.1391 (0.9); 7.9548 (1.2); 7.9296 (0.7); 7.9165 (1.3); 7.9034 (0.6); 7.2751 (0.6); 7.2625 (1.2); 7.2498 (0.9); 7.1450 (2.3); 7.1324 (1.9); 4.1245 (0.4); 4.1139 (0.4); 4.0985 (0.9); 4.0879 (0.9); 4.0722 (0.4); 4.0617 (0.4); 3.3363 (0.2); 3.3339 (0.7); 3.3250 (28.7); 3.3149 (0.2); 3.3085 (0.2); 2.9008 (0.2); 2.8920 (11.0); 2.7893 (0.4); 2.7804 (16.0); 2.7413 (0.2); 2.7334 (8.8); 2.7325 (8.7); 2.6354 (0.3); 2.6266 (12.1); 2.6157 (0.3); 2.6126 (0.2); 2.6097 (0.1); 2.5247 (0.3); 2.5216 (0.4); 2.5185 (0.4); 2.5155 (0.4); 2.5097 (7.5); 2.5067 (16.6); 2.5036 (23.6); 2.5005 (16.8); 2.4975 (7.5); 2.4904 (0.3); 3.94.sup.[a] 2.4872 (0.3); 2.4646 (3.1); 2.4580 (6.7); 2.4508 (3.3); 2.3906 (0.2); 2.3874 (0.2); 2.3846 (0.2); 1.2409 (0.2); 1.2360 (0.2); 0.8536 (0.1); 0.0088 (0.2); 0.0054 (0.2); 0.0001 (7.7); 0.0057 (0.2) I- 099 [00145]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.4056 (0.8); 9.3901 (1.7); 9.3744 (0.8); 8.4698 (8.0); 8.0238 (2.0); 8.0030 (2.4); 7.9523 (1.9); 7.8161 (1.1); 7.8129 (1.2); 7.7988 (1.4); 7.7953 (2.1); 7.7921 (1.3); 7.7777 (1.1); 7.7745 (1.2); 7.6096 (1.0); 7.6069 (1.2); 7.5891 (2.0); 7.5861 (1.6); 7.5714 (1.1); 7.5687 (1.2); 7.4068 (2.4); 7.3869 (2.8); 7.3662 (2.3); 7.3468 (1.9); 7.3452 (1.9); 7.3372 (1.5); 7.3184 (2.3); 7.2766 (1.0); 7.2723 (1.1); 7.2593 (1.6); 7.2550 (1.9); 7.2407 (0.8); 7.2364 (1.1); 7.2173 (0.8); 7.2132 (1.2); 7.1979 (3.0); 7.1939 (2.5); 7.1844 (1.8); 7.1818 (2.0); 7.1691 (3.5); 7.1453 (0.5); 7.1017 (1.6); 7.0820 (1.4); 4.1991 4.54.sup.[a] (0.8); 3.3304 (65.5); 2.8897 (13.6); 2.7316 (11.0); 2.7307 (11.4); 2.5408 (0.7); 2.5240 (0.8); 2.5194 (1.3); 2.5105 (14.5); 2.5061 (31.1); 2.5016 (44.2); 2.4971 (36.6); 2.3633 (16.0); 2.3270 (11.3) I-100 [00146]
.sup.1H-NMR(600.1 MHz, d.sub.6-DMSO): = 9.4018 (0.4); 9.3915 (1.0); 9.3811 (0.4); 8.3211 (0.9); 8.3073 (1.0); 8.2989 (1.6); 8.1718 (4.6); 8.1495 (0.7); 8.1482 (0.8); 8.1352 (0.9); 7.9547 (1.1); 7.9244 (0.7); 7.9113 (1.3); 7.8982 (0.6); 7.3629 (1.5); 7.3497 (1.7); 7.1458 (1.6); 7.1299 (0.8); 7.1166 (0.7); 4.1165 (0.4); 4.1059 (0.4); 4.0914 (0.9); 4.0810 (0.9); 4.0662 (0.4); 4.0560 (0.4); 3.3247 (39.1); 2.8920 (9.6); 2.8844 (0.1); 2.7713 (16.0); 2.7333 (7.7); 2.7324 (7.5); 2.6186 (0.1); 2.6155 (0.2); 2.6125 (0.1); 2.5398 (12.0); 2.5245 (0.4); 2.5215 (0.4); 2.5184 (0.4); 2.5096 (7.5); 2.5066 (17.0); 2.5035 (24.1); 2.5004 (17.2); 2.4973 (7.7); 2.4551 (4.3); 2.3905 (0.1); 2.3873 (0.2); 2.3843 (0.1); 2.3108 (6.3); 1.2403 (0.2); 1.2359 (0.2); 0.8537 (0.1); 0.0054 (0.2); 0.0001 (8.2); 0.0057 (0.2) 3.98.sup.[a] I-101 [00147]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.3982 (0.9); 9.3826 (1.8); 9.3672 (0.9); 8.5857 (8.4); 8.0172 (2.2); 7.9963 (2.7); 7.8124 (1.2); 7.8093 (1.3); 7.7950 (1.5); 7.7917 (2.2); 7.7741 (1.2); 7.7709 (1.2); 7.6021 (1.2); 7.5998 (1.2); 7.5818 (2.1); 7.5640 (1.2); 7.5615 (1.2); 7.4100 (2.7); 7.3900 (3.1); 7.3470 (2.4); 7.3294 (6.2); 7.3093 (6.5); 7.2024 (5.2); 7.1820 (4.4); 7.1748 (3.6); 7.1075 (1.8); 7.0875 (1.6); 4.2076 (0.8); 3.3386 (117.9); 2.8898 (0.8); 2.7315 (0.7); 2.5242 (0.9); 2.5064 (38.2); 2.5020 (52.5); 2.4976 (38.8); 2.3320 (12.4); 2.2940 (16.0) 4.60.sup.[a] I-102 [00148]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.2690 (1.1); 9.2538 (2.3); 9.2385 (1.1); 7.9706 (9.3); 7.9536 (0.5); 7.5333 (0.4); 7.5250 (3.6); 7.5199 (1.7); 7.5117 (4.0); 7.5030 (4.7); 7.4950 (1.8); 7.4896 (4.4); 7.4817 (0.5); 7.3970 (9.8); 7.3725 (3.6); 7.3526 (4.1); 7.3224 (0.4); 7.3144 (4.2); 7.3092 (1.4); 7.2978 (1.4); 7.2924 (7.6); 7.2755 (1.2); 7.2703 (3.5); 7.2624 (0.4); 7.2344 (0.4); 7.1132 (4.2); 7.0800 (2.3); 7.0602 (2.0); 4.0714 (1.2); 4.0557 (1.2); 4.0339 (2.6); 4.0184 (2.5); 3.9962 (1.3); 3.9807 (1.2); 3.3322 (47.6); 2.8913 (3.1); 2.7321 (2.7); 2.6720 (0.3); 2.5256 (1.0); 2.5209 (1.4); 2.5120 (19.7); 2.5077 (41.0); 2.5032 (55.0); 4.51.sup.[a] 2.4986 (40.0); 2.4943 (19.6); 2.4403 (11.3); 2.3300 (0.4); 2.2565 (16.0); 1.9832 (1.0) I-103 [00149]
.sup.1H-NMR(600.1 MHz, d.sub.6-DMSO): = 9.3470 (0.5); 9.3367 (1.0); 9.3263 (0.5); 8.3222 (0.9); 8.3085 (1.0); 8.2991 (1.6); 8.1998 (4.6); 8.1460 (0.8); 8.1329 (0.9); 7.9546 (1.0); 7.9217 (0.7); 7.9086 (1.3); 7.8955 (0.6); 7.3550 (1.6); 7.3066 (0.3); 7.3039 (0.3); 7.2933 (1.6); 7.2905 (1.7); 7.2862 (2.3); 7.2729 (0.4); 4.0898 (0.4); 4.0797 (0.4); 4.0654 (1.0); 4.0550 (1.0); 4.0408 (0.5); 4.0304 (0.4); 3.3250 (30.9); 2.8920 (8.7); 2.8811 (0.1); 2.7680 (16.0); 2.7333 (6.8); 2.7325 (6.8); 2.6186 (0.1); 2.6155 (0.2); 2.6125 (0.1); 2.5547 (12.2); 2.5246 (0.3); 2.5215 (0.4); 2.5184 (0.4); 2.5097 (7.2); 2.5066 (16.2); 2.5035 (23.1); 2.5004 (16.6); 2.4974 (7.6); 2.3905 (0.1); 2.3874 (0.2); 2.3842 (0.1); 2.2900 (8.6); 2.2712 (6.4); 0.0053 (0.2); 0.0001 (7.9); 0.0057 (0.3) 3.91.sup.[a] I-104 [00150]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.4069 (1.1); 9.3913 (2.4); 9.3757 (1.2); 8.7490 (9.7); 8.0730 (2.9); 8.0520 (3.6); 7.8689 (1.6); 7.8511 (2.8); 7.8329 (1.4); 7.8304 (1.6); 7.6424 (1.6); 7.6242 (2.7); 7.6042 (1.7); 7.4186 (1.0); 7.3953 (7.5); 7.3817 (3.0); 7.3749 (7.3); 7.3626 (1.5); 7.1755 (3.5); 7.1618 (7.0); 7.1581 (6.6); 7.1509 (2.0); 7.1432 (2.0); 7.1374 (2.4); 7.1270 (2.7); 7.1065 (1.2); 7.1003 (0.9); 7.0871 (2.4); 7.0670 (2.1); 4.2280 (0.8); 4.2121 (1.2); 4.1966 (1.0); 3.3371 (98.4); 2.8899 (0.4); 2.7315 (0.3); 2.5246 (0.8); 2.5066 (31.5); 2.5024 (42.6); 2.4981 (33.8); 2.3273 (16.0); 2.0040 (1.2) 4.35.sup.[a] I-105 [00151]
.sup.1H-NMR(600.1 MHz, d.sub.6-DMSO): = 9.3776 (0.4); 9.3674 (1.0); 9.3570 (0.5); 8.3218 (0.8); 8.3079 (1.0); 8.3000 (1.5); 8.2220 (4.4); 8.1464 (0.7); 8.1452 (0.8); 8.1322 (0.9); 7.9548 (1.0); 7.9211 (0.7); 7.9080 (1.3); 7.8949 (0.6); 7.6396 (1.1); 7.6356 (0.5); 7.6289 (0.8); 7.6248 (4.6); 7.6149 (4.3); 7.6108 (0.8); 7.6040 (0.4); 7.6001 (1.1); 4.1435 (0.4); 4.1332 (0.4); 4.1193 (0.9); 4.1089 (0.9); 4.0952 (0.4); 4.0847 (0.4); 3.3254 (41.4); 3.3115 (0.1); 2.8923 (9.3); 2.8836 (0.1); 2.7705 (16.0); 2.7335 (7.5); 2.7326 (7.5); 2.6189 (0.1); 2.6158 (0.2); 2.6127 (0.1); 2.5350 (11.8); 2.5249 (0.4); 2.5218 (0.5); 2.5187 (0.4); 2.5100 (7.8); 2.5069 (17.8); 2.5038 (25.3); 2.5007 (18.1); 2.4977 (8.2); 2.3907 (0.1); 2.3877 (0.2); 2.3846 (0.1); 0.0054 (0.2); 0.0001 (9.7); 0.0057 (0.3) 3.74.sup.[a] I-106 [00152]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.4144 (1.2); 9.3989 (2.5); 9.3833 (1.2); 8.6583 (10.2); 8.0346 (2.9); 8.0138 (3.5); 7.8325 (1.5); 7.8295 (1.7); 7.8151 (2.0); 7.8119 (2.9); 7.7942 (1.5); 7.7911 (1.6); 7.6181 (1.5); 7.6156 (1.6); 7.5977 (2.8); 7.5949 (2.3); 7.5800 (1.6); 7.5774 (1.6); 7.5436 (0.5); 7.5302 (0.5); 7.5217 (0.6); 7.5082 (0.6); 7.4989 (0.4); 7.4907 (3.4); 7.4858 (1.8); 7.4775 (3.8); 7.4743 (2.7); 7.4686 (4.5); 7.4607 (1.9); 7.4554 (4.1); 7.4475 (0.5); 7.4107 (3.4); 7.3908 (3.9); 7.3663 (3.1); 7.3454 (2.6); 7.2531 (4.3); 7.2310 (7.8); 7.2088 (3.6); 7.2009 (0.4); 7.1730 (4.3); 7.1073 (2.3); 7.0875 (2.1); 4.2252 (1.1); 4.2096 (1.5); 4.1937 (1.0); 3.3294 (52.4); 2.8901 (0.6); 2.7319 (0.5); 2.6709 (0.3); 4.33.sup.[a] 2.5241 (1.1); 2.5062 (46.0); 2.5019 (62.7); 2.4977 (48.1); 2.3293 (16.0); 2.0153 (0.3); 1.9986 (0.3); 1.9830 (2.2) I-107 [00153]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.2741 (0.9); 9.2587 (1.8); 9.2430 (0.9); 7.5871 (7.1); 7.3737 (8.2); 7.3582 (3.1); 7.3465 (3.1); 7.3269 (3.6); 7.2258 (3.2); 7.1178 (4.7); 7.0909 (2.4); 7.0673 (1.6); 4.0765 (0.8); 4.0610 (0.9); 4.0391 (1.9); 4.0236 (1.9); 4.0014 (1.0); 3.9858 (0.9); 3.3351 (25.4); 3.3305 (32.2); 2.8910 (2.3); 2.7321 (1.9); 2.5251 (0.8); 2.5203 (1.2); 2.5116 (15.1); 2.5074 (31.2); 2.5029 (41.8); 2.4984 (31.1); 2.4941 (15.7); 2.4467 (8.6); 2.3150 (15.2); 2.2838 (0.4); 2.2652 (12.2); 2.2342 (16.0) 5.18.sup.[a] I-108 [00154]
.sup.1H-NMR(600.1 MHz, d.sub.6-DMSO): = 9.3792 (0.6); 9.3709 (1.2); 9.3615 (0.6); 8.3307 (1.4); 8.3171 (1.6); 8.3063 (6.3); 8.2991 (3.8); 8.1504 (1.2); 8.1374 (1.3); 7.9549 (1.7); 7.9273 (0.7); 7.9143 (1.3); 7.9011 (0.6); 7.5575 (1.0); 7.5440 (1.6); 7.4934 (1.4); 7.4800 (0.9); 7.4526 (2.3); 7.1172 (1.1); 7.0240 (2.7); 6.9309 (1.3); 6.0589 (0.4); 6.0546 (0.5); 6.0466 (0.5); 6.0421 (0.4); 5.9804 (0.4); 5.9758 (0.5); 5.9681 (0.5); 5.9635 (0.4); 3.8252 (0.1); 3.8210 (0.2); 3.8161 (0.2); 3.8115 (0.2); 3.8074 (0.1); 3.8006 (0.2); 3.7966 (0.4); 3.7919 (0.4); 3.7873 (0.4); 3.56.sup.[a] 3.7832 (0.2); 3.7747 (0.1); 3.7712 (0.2); 3.7655 (0.2); 3.7624 (0.3); 3.7503 (0.6); 3.7472 (0.5); 3.7412 (0.7); 3.7315 (0.4); 3.7256 (0.4); 3.7152 (0.5); 3.7068 (0.4); 3.6944 (0.2); 3.6803 (0.1); 3.3418 (0.1); 3.3366 (0.3); 3.3257 (44.0); 2.8920 (15.3); 2.7915 (0.1); 2.7806 (12.9); 2.7745 (13.1); 2.7334 (11.8); 2.7325 (12.0); 2.6332 (0.2); 2.6221 (16.0); 2.6097 (0.1); 2.5248 (0.6); 2.5217 (0.7); 2.5186 (0.7); 2.5098 (11.8); 2.5068 (26.4); 2.5037 (37.4); 2.5006 (26.6); 2.4976 (11.9); 2.4456 (11.8); 2.4246 (0.1); 2.3907 (0.2); 2.3876 (0.2); 2.3846 (0.2); 1.1709 (0.2); 0.0054 (0.4); 0.0001 (14.5); 0.0057 (0.4) I-109 [00155]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.3981 (0.8); 9.3826 (1.7); 9.3671 (0.8); 8.3713 (7.6); 7.9982 (2.1); 7.9773 (2.5); 7.9520 (0.4); 7.7876 (1.0); 7.7846 (1.2); 7.7702 (1.4); 7.7670 (2.0); 7.7494 (1.1); 7.7462 (1.2); 7.5889 (1.2); 7.5709 (2.0); 7.5531 (1.1); 7.5507 (1.2); 7.4137 (2.5); 7.3938 (2.8); 7.3469 (2.2); 7.3260 (1.9); 7.2198 (2.8); 7.2000 (3.5); 7.1718 (5.1); 7.1110 (1.6); 7.0909 (1.4); 7.0298 (1.6); 7.0267 (1.6); 7.0101 (1.4); 4.2255 (0.5); 4.1961 (0.8); 3.3290 (40.2); 2.8892 (2.7); 2.7306 (2.4); 2.5235 (0.7); 2.5057 (34.7); 2.5014 (46.2); 2.4969 (33.1); 2.3295 (11.7); 2.3176 (16.0); 2.2800 (14.7) 4.91.sup.[a] I-110 [00156]
.sup.1H-NMR(600.1 MHz, d.sub.6-DMSO): = 9.4003 (0.5); 9.3899 (1.0); 9.3794 (0.5); 8.3154 (0.8); 8.3015 (1.0); 8.2938 (1.6); 8.2008 (4.6); 8.1453 (0.8); 8.1323 (0.9); 7.9552 (1.2); 7.9214 (0.7); 7.9084 (1.3); 7.8953 (0.6); 7.8412 (1.6); 7.8378 (1.7); 7.6663 (1.6); 7.6520 (2.5); 7.6030 (1.3); 7.5995 (1.2); 7.5888 (0.9); 7.5854 (0.9); 4.2807 (0.4); 4.2703 (0.4); 4.2572 (0.9); 4.2467 (0.9); 4.2333 (0.5); 4.2229 (0.4); 3.3252 (38.2); 2.8929 (10.6); 2.8815 (0.1); 2.7757 (0.2); 2.7685 (16.0); 2.7339 (8.4); 2.7330 (8.2); 2.6194 (0.1); 2.6163 (0.2); 2.6132 (0.2); 2.5254 (0.4); 2.5222 (0.4); 2.5191 (0.4); 2.5104 (8.1); 2.5072 (28.0); 2.5043 (24.9); 2.5012 (17.4); 2.4981 (8.0); 2.3912 (0.1); 2.3882 (0.2); 2.3851 (0.1); 0.0054 (0.2); 0.0001 (9.2); 0.0057 (0.3) 4.09.sup.[a] I-111 [00157]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.3891 (0.9); 9.3741 (1.9); 9.3585 (1.0); 8.5678 (7.7); 8.0110 (2.2); 7.9905 (2.7); 7.9524 (2.2); 7.8051 (1.2); 7.8020 (1.3); 7.7878 (1.7); 7.7844 (2.3); 7.7812 (1.6); 7.7668 (1.2); 7.7636 (1.3); 7.6003 (1.2); 7.5977 (1.2); 7.5798 (2.2); 7.5770 (1.8); 7.5623 (1.3); 7.5595 (1.3); 7.4133 (2.5); 7.3934 (2.9); 7.3513 (2.4); 7.3305 (2.0); 7.2354 (4.0); 7.1734 (3.8); 7.1500 (9.7); 7.1311 (0.3); 7.1070 (1.9); 7.0868 (1.7); 4.2078 (1.0); 3.3251 (33.1); 2.8896 (13.9); 2.7309 (11.8); 2.5405 (0.8); 2.5234 (1.0); 2.5054 (45.4); 2.5012 (58.0); 2.4968 (44.7); 2.3313 (12.6); 2.2071 (16.0); 2.1780 (16.0) 4.88.sup.[a] I-112 [00158]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.2625 (1.2); 9.2472 (2.4); 9.2319 (1.2); 8.1591 (7.9); 7.6416 (0.3); 7.6363 (0.3); 7.6222 (0.4); 7.6166 (0.5); 7.6094 (0.4); 7.5949 (0.3); 7.5902 (0.3); 7.5496 (1.1); 7.5444 (1.2); 7.5325 (1.8); 7.5248 (2.0); 7.5172 (1.5); 7.5117 (2.4); 7.5060 (2.0); 7.4989 (1.4); 7.4899 (1.6); 7.4852 (2.1); 7.4725 (0.8); 7.4640 (1.2); 7.4386 (8.7); 7.4246 (0.4); 7.3665 (3.3); 7.3466 (3.8); 7.3271 (0.5); 7.3166 (0.4); 7.3108 (0.4); 7.2740 (1.5); 7.2693 (1.4); 7.2638 (1.3); 7.2583 (1.2); 7.2525 (1.3); 7.2477 (1.1); 7.1136 (4.4); 7.0692 (2.4); 7.0493 (2.1); 5.0319 (0.6); 4.2266 (0.5); 4.2104 (1.1); 4.1949 (0.5); 4.0705 4.63.sup.[a] (1.2); 4.0551 (1.2); 4.0331 (2.6); 4.0176 (2.5); 3.9953 (1.3); 3.9800 (1.2); 3.3372 (41.9); 3.3327 (52.2); 2.8962 (0.8); 2.7373 (0.7); 2.6765 (0.4); 2.5117 (48.8); 2.5075 (59.0); 2.5035 (43.0); 2.4359 (11.7); 2.3348 (0.4); 2.2623 (16.0); 2.0754 (0.7); 2.0590 (0.7); 2.0120 (4.2) I-113 [00159]
.sup.1H-NMR(600.1 MHz, d.sub.6-DMSO): = 9.4323 (0.4); 9.4220 (1.0); 9.4116 (0.5); 8.3201 (0.8); 8.3040 (1.1); 8.2995 (1.6); 8.1959 (4.4); 8.1488 (0.7); 8.1476 (0.8); 8.1357 (0.8); 8.1345 (0.9); 7.9545 (1.4); 7.9243 (0.7); 7.9113 (1.3); 7.8982 (0.6); 7.6062 (1.3); 7.6040 (1.4); 7.5441 (0.7); 7.5414 (0.6); 7.5302 (0.8); 7.5274 (0.8); 7.4163 (1.9); 7.4022 (1.6); 4.1396 (0.4); 4.1293 (0.4); 4.1148 (0.9); 4.1043 (0.8); 4.0898 (0.4); 4.0795 (0.4); 3.3253 (60.2); 3.3107 (0.1); 2.8922 (12.6); 2.7734 (16.0); 2.7332 (10.1); 2.7323 (9.9); 2.6186 (0.1); 2.6155 (0.2); 2.6124 (0.1); 2.5345 (11.8); 2.5246 (0.5); 2.5214 (0.6); 2.5184 (0.5); 2.5096 (9.5); 2.5066 (21.6); 2.5035 (30.9); 2.5004 (23.6); 2.4973 (13.5); 2.3905 (0.2); 2.3874 (0.2); 2.3843 (0.2); 0.0054 (0.3); 0.0001 (10.4); 0.0057 (0.3) 4.20.sup.[a] I-114 [00160]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.4084 (0.6); 9.3931 (1.4); 9.3773 (0.7); 8.6771 (5.2); 8.0445 (1.6); 8.0237 (2.0); 7.9523 (0.6); 7.8388 (0.8); 7.8359 (0.9); 7.8183 (1.6); 7.8005 (0.8); 7.7975 (0.9); 7.6174 (0.9); 7.5992 (1.5); 7.5792 (0.9); 7.4030 (1.9); 7.3831 (2.2); 7.3675 (1.8); 7.3466 (1.5); 7.2953 (1.2); 7.2749 (2.8); 7.2543 (1.6); 7.1702 (2.4); 7.0982 (1.3); 7.0780 (1.2); 6.9265 (2.6); 6.9198 (2.6); 6.9149 (2.5); 6.9004 (1.5); 6.8946 (1.1); 6.8798 (1.2); 6.8743 (1.1); 4.2012 (0.6); 3.7474 (0.4); 3.7145 (16.0); 3.3304 (23.8); 2.8896 (4.1); 2.7313 (3.6); 4.29.sup.[a] 2.5405 (0.4); 2.5237 (0.6); 2.5058 (24.4); 2.5014 (34.1); 2.4969 (28.6); 2.3300 (9.0) I-115 [00161]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.4049 (0.5); 9.3893 (1.1); 9.3736 (0.5); 8.5381 (5.3); 7.9964 (1.3); 7.9758 (1.6); 7.7883 (0.7); 7.7851 (0.8); 7.7710 (0.9); 7.7676 (1.3); 7.7642 (0.7); 7.7500 (0.7); 7.7467 (0.7); 7.5882 (0.7); 7.5855 (0.7); 7.5677 (1.3); 7.5647 (0.9); 7.5500 (0.7); 7.5473 (0.7); 7.4705 (0.4); 7.4626 (3.7); 7.4573 (1.1); 7.4458 (1.2); 7.4405 (4.1); 7.4325 (0.4); 7.4228 (1.6); 7.4028 (1.8); 7.3345 (1.3); 7.3147 (1.1); 7.1796 (1.8); 7.1221 (1.0); 7.1021 (0.9); 6.9975 (0.4); 6.9896 (3.9); 6.9843 (1.2); 6.9727 (1.1); 6.9674 (3.6); 6.9595 (0.3); 4.2178 (0.4); 3.7690 (16.0); 3.3334 (47.5); 2.8894 (0.3); 2.5106 (13.1); 2.5061 (19.8); 2.5016 (23.3); 2.4970 (16.2); 2.4925 (7.7); 2.3330 (7.0) 4.24.sup.[a] I-116 [00162]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.4033 (1.2); 9.3879 (2.5); 9.3723 (1.2); 8.7170 (11.7); 8.0921 (3.0); 8.0712 (3.5); 7.9523 (1.6); 7.8896 (1.5); 7.8864 (1.9); 7.8723 (2.0); 7.8688 (3.1); 7.8654 (2.0); 7.8512 (1.6); 7.8479 (1.8); 7.6535 (1.4); 7.6508 (1.7); 7.6330 (2.9); 7.6300 (2.4); 7.6153 (1.6); 7.6125 (1.8); 7.5563 (2.8); 7.5525 (3.5); 7.5368 (3.0); 7.5331 (3.8); 7.4110 (3.2); 7.3901 (2.7); 7.3810 (3.6); 7.3610 (4.0); 7.2988 (1.1); 7.2946 (1.4); 7.2802 (2.9); 7.2760 (3.1); 7.2611 (2.3); 7.2565 (2.4); 7.2495 (2.2); 7.2454 (2.5); 7.2301 (2.8); 7.2264 (3.4); 7.2115 (1.3); 7.2078 (1.4); 7.1579 (4.3); 7.0761 (2.3); 7.0565 (2.0); 6.9673 (2.6); 6.9633 (3.1); 6.9480 (2.5); 6.9439 (2.8); 4.1925 (1.0); 3.3325 (57.8); 4.51.sup.[a] 2.8897 (11.7); 2.7309 (9.8); 2.5410 (0.7); 2.5242 (0.7); 2.5195 (1.1); 2.5107 (14.5); 2.5063 (32.0); 2.5018 (44.3); 2.4973 (33.9); 2.4930 (17.7); 2.4762 (11.5); 2.3260 (16.0) I-117 [00163]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.4212 (1.2); 9.4057 (2.4); 9.3901 (1.2); 8.7492 (10.9); 8.0750 (3.0); 8.0540 (3.6); 7.8738 (1.4); 7.8708 (1.7); 7.8566 (1.8); 7.8532 (2.9); 7.8355 (1.5); 7.8324 (1.6); 7.6465 (1.7); 7.6285 (2.8); 7.6108 (1.5); 7.6083 (1.8); 7.4009 (3.5); 7.3959 (4.3); 7.3760 (6.4); 7.3621 (8.0); 7.3573 (14.6); 7.3434 (1.2); 7.3385 (0.9); 7.3331 (0.4); 7.3303 (0.4); 7.3162 (2.3); 7.3103 (3.1); 7.3050 (1.2); 7.3004 (1.4); 7.2951 (1.9); 7.2897 (1.3); 7.1629 (4.2); 7.0825 (2.3); 7.0625 (2.0); 4.2110 (0.9); 3.3607 (0.4); 3.3378 (112.9); 2.8900 (0.8); 2.7315 (0.7); 2.5251 (0.8); 2.5204 (1.2); 2.5112 (15.7); 2.5071 (33.2); 4.70.sup.[a] 2.5027 (45.5); 2.4981 (35.4); 2.4935 (23.5); 2.3249 (16.0); 1.0993 (0.6); 1.0830 (0.6) I-118 [00164]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.4068 (1.1); 9.3914 (2.5); 9.3757 (1.2); 8.7093 (11.8); 8.0571 (2.9); 8.0364 (3.5); 7.8553 (1.6); 7.8521 (1.7); 7.8380 (2.0); 7.8346 (3.0); 7.8312 (1.7); 7.8170 (1.6); 7.8136 (1.6); 7.6324 (1.5); 7.6297 (1.7); 7.6119 (2.9); 7.6089 (2.2); 7.5942 (1.6); 7.5915 (1.7); 7.4329 (0.6); 7.4265 (5.9); 7.4213 (2.2); 7.4101 (2.8); 7.4047 (12.2); 7.3982 (5.1); 7.3787 (5.8); 7.3689 (2.0); 7.3627 (14.2); 7.3462 (2.1); 7.3409 (5.8); 7.3345 (0.7); 7.1671 (4.1); 7.0945 (2.2); 7.0746 (2.0); 4.2015 (0.9); 3.3291 (54.9); 2.8900 (1.0); 2.7318 (0.8); 4.72.sup.[a] 2.5242 (0.9); 2.5195 (1.3); 2.5108 (18.4); 2.5064 (39.0); 2.5018 (52.8); 2.4972 (41.3); 2.4926 (27.2); 2.3280 (16.0) I-119 [00165]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.4257 (1.1); 9.4102 (2.3); 9.3948 (1.1); 8.6533 (8.7); 8.3153 (5.7); 8.0461 (2.9); 8.0251 (3.5); 7.8403 (1.6); 7.8227 (2.8); 7.8048 (1.5); 7.8018 (1.6); 7.6228 (1.6); 7.6046 (2.7); 7.5845 (1.6); 7.4492 (1.2); 7.4425 (1.3); 7.4308 (1.3); 7.4255 (2.4); 7.4186 (2.5); 7.4090 (2.6); 7.4014 (4.7); 7.3939 (3.4); 7.3808 (6.9); 7.3723 (1.8); 7.3585 (2.7); 7.1687 (4.3); 7.1464 (1.1); 7.1414 (1.1); 7.1254 (1.9); 7.1202 (1.9); 7.0994 (3.2); 7.0803 (2.1); 4.2001 (1.0); 3.3307 (56.8); 3.3057 (2.3); 2.8908 (1.1); 2.7323 (1.0); 2.5243 (1.2); 2.5065 (42.9); 2.5021 (60.2); 2.4979 (52.4); 2.3240 (16.0) 4.37.sup.[a] I-120 [00166]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.4029 (1.2); 9.3874 (2.5); 9.3716 (1.2); 8.7501 (11.6); 8.3164 (0.6); 8.0649 (2.9); 8.0441 (3.6); 7.8648 (1.6); 7.8617 (1.7); 7.8475 (2.1); 7.8442 (3.0); 7.8409 (1.6); 7.8265 (1.6); 7.8233 (1.6); 7.6437 (1.6); 7.6412 (1.6); 7.6232 (2.9); 7.6205 (2.1); 7.6055 (1.7); 7.6029 (1.6); 7.4995 (1.2); 7.4938 (1.3); 7.4817 (1.9); 7.4746 (1.7); 7.4727 (1.7); 7.4665 (1.6); 7.4612 (2.6); 7.4553 (1.9); 7.4479 (1.4); 7.4397 (1.6); 7.4345 (2.4); 7.4130 (1.4); 7.4016 (5.5); 7.3817 (5.0); 7.2526 (0.9); 7.2487 (1.2); 7.2430 (1.5); 7.2385 (1.3); 4.48.sup.[a] 7.2327 (1.2); 7.2269 (1.1); 7.2213 (1.3); 7.2168 (1.0); 7.1676 (4.2); 7.0938 (2.2); 7.0739 (2.0); 4.2188 (0.9); 4.1853 (0.6); 3.3288 (56.6); 3.3057 (0.4); 2.8909 (1.0); 2.7324 (0.9); 2.5417 (0.4); 2.5250 (1.0); 2.5115 (17.3); 2.5072 (34.9); 2.5026 (46.9); 2.4981 (38.6); 2.4938 (25.6); 2.3260 (16.0) I-121 [00167]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.4067 (1.1); 9.3915 (2.4); 9.3759 (1.2); 8.6719 (9.1); 8.3149 (0.3); 8.0441 (2.9); 8.0231 (3.5); 7.9524 (2.4); 7.8364 (1.6); 7.8184 (2.7); 7.8003 (1.4); 7.7979 (1.5); 7.6176 (1.6); 7.5992 (2.7); 7.5794 (1.6); 7.4027 (3.2); 7.3828 (3.7); 7.3657 (3.2); 7.3449 (2.6); 7.2840 (1.6); 7.2768 (0.6); 7.2622 (2.7); 7.2423 (2.2); 7.1703 (4.4); 7.0975 (2.4); 7.0777 (2.1); 6.9348 (2.9); 6.9147 (2.6); 6.8765 (6.6); 6.8615 (2.8); 4.2043 (1.1); 3.9953 (1.8); 3.9780 (5.7); 3.9606 (5.8); 3.9431 (1.9); 3.3294 (74.7); 2.8899 (14.2); 2.7317 (12.5); 2.7311 (12.5); 2.6706 (0.4); 2.5408 (1.0); 2.5015 (63.1); 2.4978 (55.1); 2.3311 (16.0); 1.2863 (6.2); 1.2689 (12.9); 1.2510 (6.1) 4.65.sup.[a] I-122 [00168]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.4177 (0.8); 9.4019 (1.8); 9.3864 (0.9); 8.6945 (8.2); 8.0530 (2.2); 8.0320 (2.6); 7.9524 (1.9); 7.8522 (1.0); 7.8490 (1.4); 7.8349 (1.4); 7.8315 (2.3); 7.8281 (1.7); 7.8139 (1.1); 7.8105 (1.4); 7.6340 (1.0); 7.6314 (1.3); 7.6135 (2.1); 7.6106 (2.0); 7.5959 (1.1); 7.5931 (1.4); 7.4009 (6.2); 7.3827 (5.2); 7.3618 (2.1); 7.3519 (2.2); 7.3317 (3.4); 7.2792 (2.4); 7.2746 (2.7); 7.2593 (1.5); 7.2547 (1.7); 7.1655 (3.3); 7.0872 (1.8); 7.0675 (1.6); 4.2115 (0.8); 3.3310 (65.8); 2.8902 (12.9); 2.7312 (11.2); 2.5415 (0.7); 2.5246 (0.8); 2.5200 (1.2); 2.5111 (14.0); 2.5068 (31.8); 2.5022 (46.6); 2.4977 (41.8); 2.3244 (12.1); 2.3000 (16.0) 5.08.sup.[a] I-123 [00169]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.5549 (1.2); 9.5395 (2.5); 9.5235 (1.2); 8.3283 (9.7); 8.3170 (0.3); 8.3043 (2.1); 8.2957 (1.0); 8.2870 (1.7); 8.2821 (2.1); 8.0453 (2.1); 8.0345 (3.9); 8.0222 (2.7); 8.0139 (3.7); 7.9720 (3.0); 7.9514 (4.1); 7.7933 (1.8); 7.7756 (2.9); 7.7578 (1.5); 7.7549 (1.7); 7.7110 (3.3); 7.6929 (4.0); 7.6200 (1.8); 7.6174 (1.9); 7.6107 (2.7); 7.6046 (4.7); 7.5960 (7.1); 7.5854 (3.7); 7.5804 (4.0); 7.5679 (0.8); 7.5534 (2.8); 7.5332 (3.9); 7.5147 (2.2); 7.4283 (3.4); 7.4092 (6.4); 7.3898 (2.7); 7.1639 (4.4); 7.0744 (2.4); 7.0544 (2.1); 4.2526 (1.1); 3.3346 (80.5); 2.8895 (3.7); 2.7314 (3.4); 2.6722 (0.3); 2.5074 (41.7); 2.5029 (50.8); 2.4988 (39.0); 2.3296 (0.4); 2.2890 (16.0) 4.86.sup.[a] I-124 [00170]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.4548 (1.2); 9.4393 (2.5); 9.4237 (1.2); 8.6981 (11.3); 8.3154 (0.5); 8.0483 (3.0); 8.0274 (3.6); 7.9785 (5.0); 7.9530 (2.3); 7.9257 (1.9); 7.9127 (5.5); 7.9024 (2.3); 7.8910 (4.3); 7.8679 (0.4); 7.8600 (1.8); 7.8475 (3.0); 7.8438 (2.7); 7.8363 (2.6); 7.8300 (2.6); 7.8265 (3.4); 7.8230 (2.2); 7.8089 (1.6); 7.8055 (1.8); 7.6397 (1.5); 7.6370 (1.8); 7.6192 (2.9); 7.6162 (2.5); 7.6016 (1.6); 7.5988 (1.8); 7.5615 (0.8); 7.5476 (4.1); 7.5447 (3.6); 7.5364 (4.1); 7.5295 (3.0); 7.5258 (3.9); 7.5245 (3.9); 7.5125 (0.7); 7.4426 (2.9); 7.4380 (3.3); 7.4211 (2.8); 7.4161 (3.8); 7.4068 (4.9); 7.3869 (5.4); 7.1606 4.89.sup.[a] (4.4); 7.0681 (2.4); 7.0482 (2.1); 4.2219 (1.1); 3.3417 (140.2); 2.8902 (15.3); 2.7317 (13.1); 2.6723 (0.4); 2.5424 (0.7); 2.5256 (1.0); 2.5210 (1.5); 2.5121 (20.1); 2.5078 (44.2); 2.5032 (63.0); 2.4987 (54.6); 2.4946 (36.2); 2.3302 (0.5); 2.3256 (0.5); 2.3040 (16.0) I-125 [00171]
.sup.1H-NMR(400.2 MHZ, d.sub.6-DMSO): = 9.4181 (1.1); 9.4026 (2.4); 9.3874 (1.2); 8.7708 (9.0); 8.3157 (2.6); 8.0793 (2.8); 8.0585 (3.5); 7.8808 (1.5); 7.8778 (1.7); 7.8634 (2.0); 7.8602 (2.9); 7.8425 (1.5); 7.8393 (1.6); 7.6488 (1.7); 7.6309 (2.8); 7.6281 (2.3); 7.6131 (1.6); 7.6106 (1.7); 7.5550 (1.3); 7.5504 (1.4); 7.5358 (2.5); 7.5334 (2.4); 7.5177 (1.5); 7.5137 (1.6); 7.4124 (3.2); 7.3916 (2.7); 7.3805 (3.5); 7.3605 (4.0); 7.1832 (1.4); 7.1630 (4.9); 7.1564 (4.7); 7.1442 (3.2); 7.1324 (1.9); 7.1277 (2.2); 7.1158 (1.9); 7.1120 (2.7); 7.0960 (1.0); 7.0918 (1.0); 7.0693 (2.4); 7.0496 (2.1); 4.2247 (0.8); 4.1934 (1.1); 3.3297 (60.8); 3.3052 4.70.sup.[a] (1.5); 2.8904 (1.4); 2.7312 (1.2); 2.6710 (0.4); 2.5244 (1.2); 2.5196 (1.9); 2.5064 (56.2); 2.5020 (75.4); 2.4976 (57.3); 2.4806 (12.1); 2.3180 (16.0); 1.9830 (0.6) I-126 [00172]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.4182 (1.2); 9.4027 (2.6); 9.3872 (1.2); 8.7527 (10.4); 8.3156 (0.4); 8.0649 (3.0); 8.0442 (3.6); 7.9535 (1.8); 7.8650 (1.5); 7.8621 (1.6); 7.8476 (2.0); 7.8444 (2.8); 7.8267 (1.6); 7.8236 (1.6); 7.6441 (1.6); 7.6259 (2.8); 7.6122 (2.7); 7.6074 (4.1); 7.5946 (2.4); 7.5905 (2.4); 7.4521 (1.0); 7.4305 (4.4); 7.4204 (2.6); 7.4151 (2.7); 7.4033 (8.8); 7.3937 (1.2); 7.3838 (6.6); 7.1653 (4.2); 7.0874 (2.3); 7.0677 (2.0); 4.2178 (0.9); 3.3320 (53.2); 2.8912 (12.6); 2.7327 (11.0); 2.6718 (0.3); 2.5421 (0.9); 2.5252 (1.0); 2.5204 (1.5); 2.5116 (19.2); 2.5074 (39.4); 2.5029 (53.9); 2.4984 (44.6); 2.3220 (16.0) 4.78.sup.[a] I-127 [00173]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.3828 (0.5); 8.6323 (2.0); 8.0234 (0.6); 8.0026 (0.7); 7.9526 (0.6); 7.8005 (0.5); 7.5873 (0.5); 7.4100 (0.7); 7.3988 (1.0); 7.3902 (0.9); 7.3826 (0.5); 7.3775 (1.9); 7.3552 (0.6); 7.3329 (2.3); 7.3160 (0.4); 7.3116 (1.0); 7.1726 (0.8); 7.1046 (0.4); 7.0845 (0.4); 3.3246 (10.2); 2.8897 (4.1); 2.7313 (3.6); 2.5188 (0.3); 2.5056 (9.9); 2.5013 (13.9); 2.4970 (10.8); 2.3297 (3.1); 1.2590 (16.0) 5.55.sup.[a] I-128 [00174]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.3985 (1.1); 9.3831 (2.4); 9.3676 (1.2); 8.8125 (10.6); 8.3155 (1.1); 8.1161 (3.0); 8.0952 (3.6); 7.9526 (1.6); 7.9177 (1.5); 7.9146 (1.8); 7.9003 (1.9); 7.8970 (3.0); 7.8937 (1.9); 7.8793 (1.5); 7.8761 (1.7); 7.6753 (1.4); 7.6728 (1.7); 7.6549 (2.8); 7.6521 (2.4); 7.6372 (1.6); 7.6346 (1.8); 7.5094 (2.9); 7.5062 (3.5); 7.4894 (3.5); 7.4861 (3.9); 7.4458 (3.2); 7.4248 (2.7); 7.3649 (3.5); 7.3449 (4.0); 7.2323 (3.0); 7.2121 (5.8); 7.1920 (3.0); 7.1476 (4.4); 7.0542 (2.3); 7.0347 (2.1); 6.8136 (3.0); 6.8105 (3.6); 6.7935 (2.9); 6.7903 (3.3); 4.1845 (1.1); 3.3331 (62.6); 3.3093 (0.8); 2.8903 (11.1); 4.96.sup.[a] 2.7315 (9.5); 2.5415 (0.5); 2.5247 (0.7); 2.5201 (1.0); 2.5110 (15.2); 2.5068 (32.9); 2.5023 (45.4); 2.4978 (35.0); 2.4935 (18.3); 2.4637 (11.6); 2.3200 (16.0) I-129 [00175]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.4217 (1.2); 9.4063 (2.5); 9.3908 (1.2); 8.8226 (10.8); 8.1010 (3.0); 8.0800 (3.6); 7.9537 (2.2); 7.9019 (1.5); 7.8989 (1.7); 7.8813 (2.8); 7.8636 (1.5); 7.8604 (1.6); 7.6726 (1.6); 7.6545 (2.8); 7.6344 (1.7); 7.5229 (2.8); 7.5184 (5.7); 7.5139 (3.4); 7.4848 (0.3); 7.4407 (3.2); 7.4199 (2.6); 7.3865 (3.5); 7.3666 (4.0); 7.3387 (13.0); 7.3341 (13.0); 7.1532 (4.2); 7.0617 (2.3); 7.0419 (2.0); 4.2131 (0.8); 3.3328 (72.5); 2.8909 (15.5); 2.7323 (13.9); 2.5426 (0.7); 2.5256 (0.7); 2.5077 (30.0); 2.5033 (40.4); 2.4988 (30.0); 2.4829 (11.6); 2.3200 (16.0) 5.32.sup.[a] I-130 [00176]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.3979 (1.0); 9.3826 (2.0); 9.3671 (0.9); 8.7609 (8.6); 8.3139 (6.0); 8.1024 (2.5); 8.0816 (3.0); 7.9518 (2.3); 7.9000 (1.4); 7.8823 (2.3); 7.8643 (1.2); 7.8616 (1.3); 7.7302 (4.4); 7.7246 (4.6); 7.6627 (1.4); 7.6442 (2.3); 7.6246 (1.5); 7.4277 (2.6); 7.4072 (2.2); 7.3706 (2.9); 7.3506 (3.3); 7.3277 (2.3); 7.3221 (2.3); 7.3062 (2.5); 7.3006 (2.5); 7.1534 (3.5); 7.0669 (1.9); 7.0474 (1.7); 6.9333 (4.1); 6.9118 (3.8); 4.1838 (0.9); 3.3903 (0.4); 3.3329 (151.5); 3.3090 (4.0); 3.0262 (0.4); 2.8902 (16.0); 2.7481 (0.4); 2.7312 (14.3); 2.6708 (0.4); 2.5411 (1.5); 2.5102 (27.0); 2.5062 (52.5); 2.5018 5.11.sup.[a] (69.8); 2.4975 (52.5); 2.4686 (9.7); 2.3230 (13.5) I-131 [00177]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.4236 (0.8); 9.4080 (1.7); 9.3925 (0.8); 8.8144 (7.6); 8.1278 (2.0); 8.1070 (2.5); 7.9536 (2.2); 7.9271 (1.1); 7.9241 (1.2); 7.9098 (1.4); 7.9065 (2.0); 7.8888 (1.1); 7.8856 (1.1); 7.6954 (0.6); 7.6895 (1.6); 7.6692 (2.0); 7.6515 (1.2); 7.6489 (1.1); 7.5878 (3.8); 7.5664 (4.6); 7.5290 (0.5); 7.5076 (0.7); 7.4555 (2.1); 7.4358 (1.8); 7.3647 (2.6); 7.3522 (2.6); 7.3456 (4.9); 7.3308 (2.0); 7.3247 (2.1); 7.1487 (2.8); 7.0479 (1.5); 7.0286 (1.4); 6.9172 (4.0); 6.9111 (3.9); 4.1987 (0.6); 3.3312 (31.6); 2.8910 (16.0); 2.7324 (13.4); 2.5422 (0.6); 2.5252 (0.6); 2.5205 (0.9); 2.5118 (13.9); 2.5074 (29.1); 2.5029 (39.0); 2.4984 (28.2); 2.4940 (13.8); 2.4697 (7.8); 2.3000 (11.0) 4.96.sup.[a] I-132 [00178]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.4143 (1.2); 9.3989 (2.4); 9.3832 (1.2); 8.7904 (10.0); 8.0836 (3.0); 8.0627 (3.6); 7.9531 (1.2); 7.8837 (1.5); 7.8809 (1.6); 7.8632 (2.8); 7.8454 (1.5); 7.8424 (1.6); 7.6563 (2.5); 7.6381 (2.8); 7.6181 (1.7); 7.6060 (5.0); 7.5992 (1.0); 7.5848 (5.8); 7.5782 (1.2); 7.5632 (5.0); 7.5579 (5.4); 7.4190 (3.6); 7.3982 (3.2); 7.3905 (3.7); 7.3704 (3.9); 7.2992 (3.2); 7.2937 (3.1); 7.2781 (2.8); 7.2725 (2.8); 7.1580 (4.3); 7.0714 (2.3); 7.0515 (2.1); 5.1518 (0.3); 4.2100 (0.9); 3.6407 (0.4); 3.6269 (0.4); 3.3319 (50.3); 2.8908 (8.1); 2.7321 (7.1); 2.6716 (0.3); 2.5419 (0.7); 2.5249 (1.0); 2.5071 (41.6); 2.5027 (55.0); 2.4983 (40.7); 2.4848 (12.0); 2.3205 (16.0); 1.9697 (0.4); 1.9530 (0.4) 5.15.sup.[a] I-133 [00179]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.4186 (1.1); 9.4032 (2.3); 9.3876 (1.1); 8.8137 (11.7); 8.3155 (3.5); 8.0995 (3.0); 8.0787 (3.6); 7.8989 (1.5); 7.8958 (1.7); 7.8816 (2.0); 7.8782 (3.0); 7.8748 (1.8); 7.8606 (1.6); 7.8573 (1.7); 7.6711 (5.4); 7.6636 (2.6); 7.6605 (2.5); 7.6498 (6.6); 7.6430 (3.9); 7.6250 (1.9); 7.6222 (2.0); 7.4190 (6.8); 7.3974 (6.0); 7.3825 (3.7); 7.3625 (4.1); 7.1568 (4.2); 7.0722 (2.3); 7.0522 (2.0); 4.1893 (0.9); 3.3320 (53.8); 3.3073 (1.4); 2.8906 (1.7); 2.7317 (1.4); 2.6714 (0.4); 2.5418 (0.5); 2.5250 (1.2); 2.5202 (1.7); 2.5114 (20.3); 2.5070 (42.6); 2.5025 (57.2); 2.4980 (41.9); 2.4936 (20.5); 2.4739 (11.3); 2.3218 (16.0); 1.1150 (0.5); 1.0990 (0.5) 4.84.sup.[a] I-134 [00180]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.4418 (1.2); 9.4264 (2.5); 9.4106 (1.2); 8.7782 (11.7); 8.3166 (0.9); 8.0825 (3.0); 8.0618 (3.6); 7.8819 (1.6); 7.8788 (1.8); 7.8646 (2.0); 7.8612 (3.0); 7.8580 (1.8); 7.8436 (1.6); 7.8404 (1.7); 7.6668 (4.7); 7.6602 (3.3); 7.6564 (3.1); 7.6516 (2.1); 7.6387 (4.8); 7.6355 (4.6); 7.6209 (1.9); 7.6182 (2.0); 7.5964 (0.8); 7.5921 (1.0); 7.5789 (7.8); 7.5623 (2.4); 7.5425 (0.6); 7.4229 (3.2); 7.4020 (2.8); 7.3937 (3.8); 7.3737 (4.1); 7.1565 (4.2); 7.0674 (2.3); 7.0476 (2.0); 4.2050 (1.0); 3.3288 (55.0); 3.3050 (0.6); 2.8903 (1.9); 4.80.sup.[a] 2.7319 (1.6); 2.5417 (0.5); 2.5114 (19.2); 2.5070 (37.6); 2.5025 (49.6); 2.4980 (36.7); 2.4934 (19.8); 2.4849 (12.1); 2.3120 (16.0) I-135 [00181]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.4184 (1.2); 9.4029 (2.5); 9.3874 (1.2); 8.7651 (10.8); 8.3169 (0.8); 8.0834 (3.0); 8.0625 (3.6); 7.9541 (1.3); 7.8809 (1.5); 7.8779 (1.7); 7.8635 (1.9); 7.8603 (2.9); 7.8425 (1.5); 7.8395 (1.6); 7.6530 (1.6); 7.6350 (2.8); 7.6170 (1.6); 7.6148 (1.7); 7.4912 (1.6); 7.4716 (3.7); 7.4520 (2.4); 7.4146 (3.2); 7.3926 (5.8); 7.3722 (4.0); 7.3356 (3.1); 7.3150 (2.4); 7.2940 (7.3); 7.2745 (1.9); 7.2721 (1.9); 7.1616 (4.3); 7.0753 (2.3); 7.0553 (2.1); 4.2060 (0.9); 3.3337 (79.8); 2.8913 (8.6); 2.7329 (7.4); 2.5426 (0.9); 2.5258 (0.7); 2.5210 (1.1); 2.5079 (32.6); 2.5035 (44.0); 2.4990 (33.2); 2.4948 (18.8); 2.4866 (12.2); 2.3210 (16.0) 4.94.sup.[a] I-136 [00182]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.4151 (1.1); 9.3997 (2.4); 9.3842 (1.2); 8.7490 (11.2); 8.3156 (3.5); 8.0647 (3.0); 8.0438 (3.6); 7.9530 (0.4); 7.8650 (1.5); 7.8619 (1.8); 7.8477 (1.9); 7.8443 (3.0); 7.8410 (1.9); 7.8267 (1.5); 7.8235 (1.7); 7.6395 (1.4); 7.6371 (1.7); 7.6191 (2.8); 7.6163 (2.3); 7.6014 (1.6); 7.5988 (1.8); 7.4590 (0.6); 7.4516 (5.9); 7.4465 (2.5); 7.4350 (2.5); 7.4294 (10.1); 7.4223 (1.4); 7.3981 (3.8); 7.3785 (4.2); 7.3707 (3.4); 7.3599 (6.2); 7.3393 (3.8); 7.1646 (4.2); 7.0898 (2.3); 7.0698 (2.0); 4.2008 (1.0); 3.3346 (105.1); 3.3108 (2.0); 2.8906 (2.9); 2.7318 (2.5); 2.5419 (0.6); 2.5250 (0.9); 2.5203 (1.3); 2.5114 (17.9); 2.5071 (38.2); 2.5027 (52.4); 2.4981 (40.8); 2.4936 (26.0); 2.3230 (16.0) 4.97.sup.[a] I-137 [00183]
.sup.1H-NMR(400.1 MHz, CDCl3): = 8.3196 (3.8); 8.2725 (2.1); 8.2525 (2.3); 7.9693 (0.3); 7.8766 (1.9); 7.8611 (8.4); 7.6956 (1.8); 7.6760 (3.0); 7.6563 (1.4); 7.3510 (1.6); 7.3317 (4.7); 7.3130 (4.3); 7.2769 (4.7); 7.2735 (7.0); 7.2615 (10.7); 7.2562 (4.3); 7.2475 (2.5); 7.2293 (3.0); 7.2148 (1.0); 7.2114 (1.2); 6.7365 (1.4); 6.7234 (0.9); 5.2973 (0.4); 3.8038 (0.5); 3.7993 (0.5); 3.7886 (1.0); 3.7842 (1.0); 3.7696 (1.2); 3.7659 (1.0); 3.7550 (1.4); 3.7506 (1.5); 3.7398 (0.9); 3.7355 2.98.sup.[a] (0.9); 3.6664 (0.3); 3.6299 (0.8); 3.6197 (0.9); 3.6151 (0.9); 3.6060 (1.2); 3.5965 (1.3); 3.5924 (1.0); 3.5860 (0.8); 3.5818 (1.3); 3.5727 (0.9); 3.5631 (0.7); 3.5586 (0.7); 3.5484 (0.6); 3.1498 (0.7); 3.1328 (1.1); 3.1111 (1.1); 3.0943 (0.7); 2.9464 (2.6); 2.8593 (2.2); 2.6273 (15.7); 2.6239 (16.0); 2.0007 (0.8); 1.6464 (0.7); 1.3870 (12.3); 1.3696 (12.4); 1.3519 (0.6); 1.2564 (0.8); 0.0079 (0.3); 0.0002 (10.8); 0.0082 (0.6) I-138 [00184]
.sup.1H-NMR(400.1 MHz, CDCl3): = 8.3898 (3.9); 8.3360 (2.1); 8.3160 (2.2); 8.1114 (4.6); 8.0969 (4.5); 7.8834 (1.9); 7.8638 (2.3); 7.7826 (0.5); 7.7682 (1.0); 7.7532 (0.6); 7.7436 (0.6); 7.7280 (1.0); 7.7096 (2.0); 7.6895 (2.9); 7.6699 (1.3); 7.6099 (2.2); 7.5899 (2.8); 7.4699 (2.2); 7.4500 (1.7); 7.3610 (3.5); 7.2613 (9.1); 6.7744 (1.6); 6.6335 (3.5); 6.4926 (1.7); 6.0381 (0.8); 6.0233 (0.8); 5.9193 (0.8); 5.9045 (0.8); 4.1001 (0.3); 4.0930 (0.4); 4.0848 (0.3); 4.0715 (0.3); 4.0632 (0.4); 4.0561 (0.6); 4.0491 (0.4); 4.0406 (0.3); 4.0247 (0.3); 4.0181 (0.4); 3.19.sup.[a] 4.0092 (0.4); 4.0022 (0.4); 3.9967 (0.5); 3.9823 (2.6); 3.9700 (2.4); 3.8607 (0.5); 3.8456 (0.6); 3.8419 (0.6); 3.8263 (0.6); 3.8052 (0.9); 3.7902 (1.0); 3.7706 (0.6); 3.7538 (0.4); 3.7498 (0.4); 3.7349 (0.4); 2.7230 (12.2); 2.6959 (12.5); 2.4851 (16.0); 1.6200 (4.1); 1.2551 (1.2); 1.2373 (1.1); 1.2198 (0.6); 0.0079 (0.4); 0.0002 (10.8); 0.0083 (0.4) I-139 [00185]
.sup.1H-NMR(400.1 MHz, CDCl3): = 8.3603 (1.8); 8.3491 (1.1); 8.3286 (1.0); 8.0275 (4.6); 7.8773 (0.9); 7.8578 (1.1); 7.7067 (0.8); 7.6871 (1.4); 7.6675 (0.6); 7.2626 (4.5); 7.0924 (2.0); 7.0720 (2.1); 6.7441 (0.4); 6.7311 (0.7); 6.7186 (0.4); 6.5140 (1.8); 6.5081 (2.5); 6.4909 (1.6); 6.4849 (1.0); 6.4704 (1.4); 6.4644 (1.0); 3.8339 (14.8); 3.8006 (16.0); 3.7076 (0.9); 3.6922 (2.1); 3.6769 (2.0); 3.6615 (1.0); 2.9512 (0.5); 2.9316 (1.6); 2.9151 (2.5); 2.8990 (1.4); 2.8704 (0.4); 2.7713 (13.3); 2.0686 (0.4); 0.0002 (5.3) 2.89.sup.[a] I-140 [00186]
.sup.1H-NMR(400.1 MHz, CDCl3): = 8.3716 (2.5); 8.3306 (1.3); 8.3105 (1.4); 8.1018 (6.0); 7.8822 (1.3); 7.8628 (1.9); 7.8541 (1.4); 7.8381 (0.6); 7.7063 (1.1); 7.6865 (1.9); 7.6669 (0.9); 7.2613 (3.5); 7.2215 (0.7); 7.2026 (1.6); 7.1836 (1.3); 7.0895 (3.5); 7.0705 (2.5); 4.2025 (0.6); 4.1870 (0.6); 4.1662 (1.2); 4.1634 (1.2); 4.1506 (1.2); 4.1475 (1.2); 4.1258 (0.7); 4.1101 (0.6); 3.9630 (2.6); 3.4709 (0.6); 2.8534 (0.4); 2.7777 (16.0); 2.5037 (5.4); 2.4926 (11.3); 2.4812 (6.0); 2.4188 (0.4); 1.6913 (0.4); 0.0002 (4.1) 3.50.sup.[a] I-141 [00187]
.sup.1H-NMR(400.1 MHz, d.sub.6-DMSO): = 9.2429 (1.2); 9.2276 (2.5); 9.2121 (1.3); 8.3900 (9.3); 7.9607 (0.5); 7.5834 (3.1); 7.5790 (5.8); 7.5746 (3.4); 7.4743 (9.4); 7.3448 (3.6); 7.3301 (12.8); 7.3256 (15.8); 7.0985 (4.2); 7.0204 (2.4); 7.0000 (2.1); 4.0700 (1.2); 4.0547 (1.2); 4.0330 (2.6); 4.0175 (2.6); 3.9957 (1.4); 3.9804 (1.4); 3.3171 (32.1); 2.8984 (3.6); 2.7393 (3.1); 2.5132 (12.1); 2.5088 (16.6); 2.5045 (12.7); 2.4228 (11.5); 2.2560 (16.0); 2.2173 (0.7) 5.46.sup.[a] I-142 [00188]
.sup.1H-NMR(400.1 MHz, CDCl3): = 8.3299 (2.2); 8.2942 (1.2); 8.2740 (1.3); 8.0112 (5.7); 7.8800 (1.1); 7.8604 (1.4); 7.7042 (1.0); 7.6845 (1.8); 7.6648 (0.8); 7.3904 (1.4); 7.3868 (1.4); 7.3711 (1.8); 7.3674 (1.8); 7.3395 (1.0); 7.3350 (1.2); 7.3209 (1.6); 7.3164 (1.7); 7.2672 (0.9); 7.2627 (5.0); 7.2490 (1.8); 7.2454 (1.6); 7.2307 (1.1); 7.2267 (1.0); 7.2187 (1.3); 7.2139 (1.3); 7.1996 (1.4); 7.1950 (1.4); 7.1808 (0.5); 7.1764 (0.5); 7.1015 (0.5); 7.0869 (1.0); 7.0724 (0.5); 3.8305 3.07.sup.[a] (0.9); 3.8136 (2.6); 3.7973 (4.6); 3.7808 (1.2); 3.4727 (0.6); 3.1607 (2.0); 3.1434 (4.0); 3.1261 (1.8); 2.7340 (16.0); 1.6281 (1.1); 1.2565 (0.4); 1.2499 (0.4); 1.2323 (0.5); 0.0002 (5.2) I-143 [00189]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.4947 (0.6); 9.4789 (1.3); 9.4632 (0.7); 7.5816 (1.6); 7.5764 (2.3); 7.5666 (2.5); 7.5577 (3.1); 7.4911 (5.3); 7.4863 (5.4); 7.4778 (2.9); 7.4743 (2.8); 7.4641 (0.7); 7.3769 (2.2); 7.3571 (2.5); 7.1426 (2.8); 7.1200 (1.5); 7.0997 (1.3); 4.0823 (0.7); 4.0660 (0.7); 4.0432 (1.6); 4.0269 (1.6); 4.0039 (0.8); 3.9878 (0.8); 3.3249 (24.4); 2.8909 (0.7); 2.7622 (16.0); 2.7323 (0.7); 2.5070 (24.0); 2.5029 (32.0); 2.4986 (24.7); 2.4716 (7.2); 2.2935 (10.0) 4.40.sup.[a] I-144 [00190]
.sup.1H-NMR(400.1 MHz, d.sub.6-DMSO): = 9.4861 (0.7); 9.4701 (1.5); 9.4541 (0.8); 7.9607 (1.1); 7.3850 (2.1); 7.3642 (4.3); 7.3012 (1.5); 7.2818 (2.9); 7.2436 (1.9); 7.2247 (1.1); 7.1520 (2.8); 7.1278 (1.6); 7.1071 (1.4); 4.0951 (0.7); 4.0791 (0.7); 4.0561 (1.6); 4.0399 (1.6); 4.0172 (0.9); 4.0009 (0.8); 3.3172 (16.5); 2.8984 (7.4); 2.7582 (16.0); 2.7394 (6.8); 2.5133 (7.4); 2.5089 (10.1); 2.5045 (7.8); 2.4811 (7.5); 2.3392 (0.7); 2.3024 (10.2); 2.2866 (11.6); 2.2494 (0.5); 2.2194 (11.6); 2.1895 (0.6) 5.05.sup.[a] I-145 [00191]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.4838 (0.6); 9.4674 (1.2); 9.4517 (0.6); 7.9525 (1.4); 7.3861 (2.8); 7.3752 (2.2); 7.3694 (2.0); 7.3638 (1.6); 7.3554 (6.8); 7.3193 (0.4); 7.3077 (1.1); 7.2997 (1.3); 7.2934 (0.8); 7.2905 (0.9); 7.1417 (2.5); 7.1191 (1.4); 7.0992 (1.3); 4.0784 (0.7); 4.0621 (0.7); 4.0395 (1.5); 4.0231 (1.4); 4.0000 (0.8); 3.9837 (0.7); 3.3242 (52.3); 2.8906 (10.3); 2.7597 (16.0); 2.7320 (8.9); 2.7309 (8.5); 2.6710 (0.4); 2.5412 (0.8); 2.5244 (0.9); 2.5197 (1.4); 2.5108 (19.6); 2.5064 (41.4); 2.5019 (55.7); 2.4975 (41.3); 2.4689 (6.6); 2.3633 (0.4); 2.3339 (12.5); 2.2931 (9.5); 2.2707 (0.9); 2.2099 (0.4); 1.9617 (0.4) 4.76.sup.[a] I-146 [00192]
.sup.1H-NMR(400.1 MHz, d.sub.6-DMSO): = 9.2551 (1.0); 7.6637 (4.4); 7.3888 (4.6); 7.3827 (2.1); 7.3625 (2.0); 7.2905 (1.3); 7.2712 (2.1); 7.2502 (2.3); 7.2104 (1.4); 7.1911 (1.0); 7.1259 (2.1); 7.0885 (1.2); 7.0685 (1.1); 4.0663 (0.5); 4.0290 (1.0); 3.9991 (0.6); 3.3170 (12.4); 2.8984 (1.8); 2.7393 (1.6); 2.5133 (5.7); 2.5088 (7.9); 2.5044 (6.1); 2.4517 (5.7); 2.3230 (0.4); 2.2708 (16.0); 2.2417 (1.0); 2.2296 (9.2) 5.17.sup.[a] I-147 [00193]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.5010 (0.6); 9.4849 (1.3); 9.4688 (0.6); 7.9533 (1.3); 7.5419 (1.6); 7.5234 (2.0); 7.4275 (1.4); 7.4246 (1.4); 7.4115 (3.4); 7.4088 (4.2); 7.3955 (0.6); 7.3791 (2.0); 7.3592 (2.3); 7.2982 (0.8); 7.2922 (0.8); 7.2797 (1.1); 7.2733 (0.9); 7.2630 (0.5); 7.2573 (0.5); 7.1450 (2.5); 7.1211 (1.4); 7.1009 (1.2); 4.0901 (0.6); 4.0742 (0.6); 4.0511 (1.4); 4.0349 (1.4); 4.0120 (0.7); 3.9957 (0.7); 3.3362 (74.1); 2.8912 (9.4); 2.7531 (16.0); 2.7327 (7.9); 2.7322 (7.9); 2.5425 (0.5); 2.5257 (0.6); 2.5209 (0.8); 2.5120 (11.9); 2.5078 (24.2); 2.5033 (32.0); 2.4989 (23.3); 2.4760 (6.5); 2.3303 (0.3); 2.2948 (9.2); 2.2705 (13.0) 4.68.sup.[a] I-148 [00194]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.4922 (0.6); 9.4763 (1.1); 9.4599 (0.6); 7.9526 (1.0); 7.4131 (1.2); 7.3928 (2.4); 7.3726 (2.7); 7.3547 (2.0); 7.1433 (4.0); 7.1407 (4.3); 7.1368 (3.4); 7.1345 (3.1); 7.1302 (3.5); 7.1276 (2.6); 7.1185 (1.3); 7.0974 (1.1); 7.0749 (1.1); 7.0728 (1.3); 7.0688 (1.1); 7.0666 (1.1); 7.0541 (1.0); 7.0518 (1.1); 7.0482 (1.0); 7.0457 (1.0); 4.0785 (0.6); 4.0621 (0.6); 4.0395 (1.3); 4.0231 (1.2); 4.0001 (0.7); 3.9840 (0.6); 3.7653 (16.0); 3.3351 (49.0); 2.8907 (6.6); 2.7677 (14.0); 2.7316 (5.8); 2.5255 (0.4); 2.5118 (9.1); 2.5076 (18.8); 2.5031 (24.9); 2.4987 (18.8); 2.4691 (5.9); 2.2936 (8.2) 4.43.sup.[a] I-149 [00195]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.4826 (0.8); 9.4669 (1.6); 9.4511 (0.9); 7.9570 (0.3); 7.4533 (3.8); 7.4333 (5.0); 7.3784 (2.1); 7.3585 (2.5); 7.3016 (4.3); 7.2819 (3.4); 7.1449 (3.1); 7.1237 (1.7); 7.1036 (1.5); 4.0819 (0.8); 4.0663 (0.8); 4.0427 (1.7); 4.0267 (1.7); 4.0039 (0.9); 3.9874 (0.8); 3.3414 (91.4); 2.8950 (1.9); 2.7579 (16.0); 2.7367 (1.8); 2.5106 (30.9); 2.5069 (36.9); 2.5025 (28.4); 2.4728 (8.1); 2.3688 (12.0); 2.3336 (0.4); 2.2975 (10.7) 4.77.sup.[a] I-150 [00196]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.5251 (0.6); 9.5093 (1.2); 9.4928 (0.6); 7.9526 (0.3); 7.5577 (0.5); 7.5421 (0.6); 7.5376 (1.2); 7.5224 (1.2); 7.5178 (1.1); 7.5025 (0.9); 7.4768 (0.7); 7.4709 (1.1); 7.4669 (1.0); 7.4540 (0.7); 7.4502 (1.1); 7.4443 (1.1); 7.4332 (2.0); 7.4300 (1.4); 7.4166 (1.0); 7.4134 (1.4); 7.4107 (1.0); 7.3721 (2.2); 7.3640 (0.8); 7.3525 (2.4); 7.3419 (1.1); 7.3273 (0.6); 7.3251 (0.6); 7.3208 (0.5); 7.3186 (0.5); 7.1421 (2.4); 7.1179 (1.3); 7.0974 (1.2); 4.0775 (0.6); 4.0614 (0.6); 4.0383 (1.4); 4.0219 (1.4); 3.9990 (0.7); 3.9825 (0.7); 3.3244 (32.8); 2.8907 (2.4); 2.7804 (16.0); 2.7313 (2.0); 2.5247 (0.7); 2.5200 (1.0); 2.5111 (13.9); 2.5068 (29.5); 2.5023 (40.1); 2.4978 (30.2); 4.51.sup.[a] 2.4936 (15.5); 2.4690 (6.4); 2.3291 (0.4); 2.2943 (8.9) I-151 [00197]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.5269 (0.6); 9.5109 (1.3); 9.4946 (0.7); 7.6643 (1.5); 7.6600 (2.9); 7.6557 (2.1); 7.5800 (0.7); 7.5758 (1.1); 7.5711 (0.7); 7.5613 (2.0); 7.5572 (3.0); 7.5524 (1.9); 7.5460 (2.2); 7.5424 (2.8); 7.5259 (2.8); 7.5069 (2.1); 7.4878 (0.7); 7.3734 (2.1); 7.3536 (2.4); 7.1423 (2.6); 7.1178 (1.4); 7.0977 (1.2); 4.0788 (0.7); 4.0626 (0.7); 4.0396 (1.5); 4.0234 (1.4); 4.0002 (0.8); 3.9842 (0.7); 3.3251 (20.0); 2.8914 (0.9); 2.7814 (16.0); 2.7327 (0.8); 2.5254 (0.5); 2.5204 (0.8); 2.5115 (10.5); 2.5075 (21.5); 2.5031 (28.7); 2.4987 (21.8); 2.4704 (6.8); 2.2951 (9.5) 4.90.sup.[a] I-152 [00198]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.5073 (0.5); 9.4918 (1.1); 9.4754 (0.5); 7.6384 (2.0); 7.6330 (0.8); 7.6247 (2.2); 7.6164 (2.4); 7.6082 (0.9); 7.6028 (2.2); 7.3740 (1.9); 7.3531 (4.0); 7.3475 (0.8); 7.3358 (0.8); 7.3304 (4.1); 7.3250 (0.8); 7.3134 (0.7); 7.3083 (1.9); 7.1428 (2.2); 7.1217 (1.2); 7.1016 (1.0); 4.0782 (0.6); 4.0619 (0.6); 4.0390 (1.3); 4.0226 (1.3); 3.9996 (0.7); 3.9834 (0.6); 3.3234 (22.4); 2.8908 (0.6); 2.7658 (16.0); 2.7320 (0.6); 2.5249 (0.6); 2.5200 (0.9); 2.5114 (11.0); 2.5070 (22.2); 2.5024 (29.2); 2.4979 (20.6); 2.4933 (9.6); 2.4700 (5.7); 2.2957 (8.2) 4.49.sup.[a] I-153 [00199]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.5168 (0.6); 9.5007 (1.3); 9.4845 (0.7); 7.6005 (2.4); 7.5953 (1.0); 7.5843 (1.4); 7.5788 (6.9); 7.5553 (6.6); 7.5391 (0.9); 7.5337 (2.4); 7.3712 (2.1); 7.3513 (2.4); 7.1412 (2.6); 7.1186 (1.4); 7.0983 (1.2); 4.0757 (0.7); 4.0594 (0.7); 4.0367 (1.5); 4.0204 (1.5); 3.9975 (0.8); 3.9812 (0.7); 3.3234 (25.2); 2.8905 (1.6); 2.7711 (16.0); 2.7322 (1.4); 2.5245 (0.6); 2.5065 (24.8); 2.5022 (32.7); 2.4978 (24.2); 2.4682 (6.8); 2.2938 (9.6) 4.89.sup.[a] I-154 [00200]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.4816 (0.6); 9.4656 (1.2); 9.4492 (0.6); 7.9525 (1.6); 7.4095 (2.3); 7.3900 (2.7); 7.3753 (2.0); 7.3554 (2.3); 7.2225 (2.4); 7.1423 (2.4); 7.1186 (1.4); 7.0972 (2.4); 7.0750 (1.3); 4.0843 (0.6); 4.0683 (0.6); 4.0458 (1.4); 4.0293 (1.4); 4.0064 (0.7); 3.9904 (0.7); 3.3303 (67.5); 2.8907 (11.6); 2.7468 (16.0); 2.7316 (10.2); 2.5418 (0.5); 2.5250 (0.8); 2.5203 (1.1); 2.5114 (14.8); 2.5070 (31.4); 2.5025 (42.6); 2.4980 (31.7); 2.4937 (16.0); 2.4724 (6.4); 2.3311 (11.0); 2.2936 (9.4); 2.2604 (0.5); 2.2490 (0.4); 2.2239 (11.9) 5.06.sup.[a] I-155 [00201]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.4687 (0.6); 9.4526 (1.2); 9.4363 (0.6); 7.9522 (1.3); 7.3738 (2.0); 7.3539 (2.3); 7.3278 (2.7); 7.2860 (0.8); 7.2822 (0.7); 7.2665 (2.1); 7.2627 (2.2); 7.2459 (3.1); 7.2261 (1.1); 7.1406 (2.6); 7.1200 (1.4); 7.0999 (1.2); 4.0758 (0.7); 4.0596 (0.7); 4.0367 (1.5); 4.0204 (1.4); 3.9976 (0.8); 3.9814 (0.7); 3.3231 (35.5); 2.8901 (9.4); 2.7510 (16.0); 2.7309 (8.1); 2.5103 (18.4); 2.5062 (35.8); 2.5017 (47.1); 2.4973 (35.1); 2.4675 (6.7); 2.3286 (0.5); 2.3238 (0.5); 2.3194 (0.5); 2.2932 (9.4); 2.2693 (11.3); 2.2374 (11.8); 2.2149 (0.6); 1.9659 (0.3) 5.05.sup.[a] I-156 [00202]
.sup.1H-NMR(400.1 MHz, d.sub.6-DMSO): = 9.2211 (2.0); 8.3697 (9.2); 7.7082 (5.1); 7.6874 (6.2); 7.4613 (9.6); 7.4405 (5.9); 7.4200 (5.3); 7.3360 (3.6); 7.3160 (4.1); 7.0966 (4.3); 7.0213 (2.4); 7.0016 (2.2); 4.0442 (1.0); 4.0316 (1.0); 4.0071 (2.1); 3.9955 (2.1); 3.9698 (1.2); 3.9585 (1.1); 3.3177 (37.5); 2.8983 (1.4); 2.7393 (1.3); 2.5132 (11.4); 2.5088 (15.7); 2.5045 (11.9); 2.4099 (11.7); 2.2493 (16.0) 4.97.sup.[a] I-157 [00203]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.4703 (0.6); 9.4547 (1.1); 9.4381 (0.6); 7.9528 (0.9); 7.4931 (0.4); 7.4856 (3.7); 7.4809 (1.4); 7.4686 (1.3); 7.4638 (4.2); 7.4565 (0.5); 7.3752 (1.8); 7.3554 (2.1); 7.1418 (2.3); 7.1219 (1.2); 7.1016 (1.1); 7.0579 (0.4); 7.0506 (4.0); 7.0286 (3.7); 7.0214 (0.5); 4.0776 (0.6); 4.0608 (0.6); 4.0383 (1.3); 4.0219 (1.3); 3.9989 (0.7); 3.9828 (0.6); 3.8136 (16.0); 3.3341 (60.7); 2.8910 (5.9); 2.7518 (13.8); 2.7321 (5.2); 2.5254 (0.6); 2.5076 (20.2); 2.5032 (26.8); 2.4988 (20.1); 2.4694 (5.9); 2.2955 (8.2) 4.41.sup.[a] I-158 [00204]
.sup.1H-NMR(400.1 MHz, d.sub.6-DMSO): = 9.2293 (2.0); 8.2069 (9.0); 7.4753 (0.7); 7.4723 (0.6); 7.4563 (1.6); 7.4535 (1.7); 7.4384 (2.1); 7.4268 (9.6); 7.4192 (1.6); 7.3574 (3.5); 7.3375 (4.0); 7.2350 (0.9); 7.2290 (1.4); 7.2118 (5.1); 7.2091 (5.1); 7.2047 (4.2); 7.2017 (3.9); 7.1861 (5.8); 7.1093 (4.3); 7.0527 (2.3); 7.0330 (2.1); 4.0560 (1.0); 4.0194 (2.1); 3.9856 (1.1); 3.3174 (27.8); 2.8980 (1.5); 2.7390 (1.3); 2.5130 (10.2); 2.5086 (13.9); 2.5042 (10.4); 2.4309 (11.5); 2.2606 (16.0) 4.53.sup.[a] I-159 [00205]
.sup.1H-NMR(600.1 MHz, d.sub.6-DMSO): = 8.9323 (0.6); 8.9230 (1.2); 8.9136 (0.6); 8.7465 (0.1); 8.7429 (0.1); 8.3554 (1.2); 8.3419 (1.2); 8.3179 (2.1); 8.2344 (6.1); 8.1216 (1.1); 8.1086 (1.2); 7.9542 (1.2); 7.9113 (1.0); 7.8981 (1.8); 7.8850 (0.8); 7.3329 (1.2); 7.3303 (0.5); 7.3203 (3.2); 7.3110 (1.0); 7.3082 (2.9); 7.2809 (2.8); 7.2785 (3.5); 7.2672 (2.0); 7.2436 (0.7); 7.2414 (1.0); 7.2392 (0.5); 7.2293 (1.6); 7.2195 (0.4); 7.2173 (0.6); 7.2150 (0.3); 6.5363 (0.4); 5.9393 (3.0); 3.5631 (1.0); 3.5513 (2.0); 3.5417 (2.0); 3.5297 (1.0); 3.3266 (16.3); 2.8913 (10.2); 2.8739 (1.7); 2.8619 (3.2); 2.8500 (1.6); 2.8442 (0.4); 2.8414 (0.4); 2.7799 2.73.sup.[a] (0.2); 2.7747 (0.1); 2.7320 (7.8); 2.6180 (0.2); 2.6148 (0.4); 2.6121 (0.1); 2.5769 (16.0); 2.5240 (0.4); 2.5209 (0.5); 2.5178 (0.4); 2.5090 (9.2); 2.5060 (20.5); 2.5029 (28.6); 2.4999 (20.3); 2.4969 (9.0); 2.3899 (0.1); 2.3868 (0.2); 2.3838 (0.1); 2.2979 (0.2); 2.0118 (0.1); 1.9990 (0.1); 1.2413 (0.3); 1.2365 (0.3); 0.8537 (0.2); 0.8419 (0.1); 0.0054 (0.2); 0.0001 (9.5); 0.0057 (0.3) I-160 [00206]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.5828 (0.4); 9.5676 (0.9); 9.5514 (0.4); 7.9581 (2.3); 7.7696 (1.0); 7.7656 (1.2); 7.7505 (1.2); 7.7465 (1.4); 7.6774 (1.0); 7.6743 (1.2); 7.6574 (1.4); 7.6543 (1.6); 7.5769 (0.7); 7.5729 (0.8); 7.5577 (1.2); 7.5541 (1.2); 7.5384 (0.7); 7.5343 (0.7); 7.4755 (0.8); 7.4723 (0.9); 7.4565 (1.3); 7.4534 (1.4); 7.4377 (0.6); 7.4347 (0.7); 7.3790 (1.5); 7.3590 (1.7); 7.1509 (1.8); 7.1245 (1.0); 7.1045 (1.0); 4.0941 (0.5); 4.0775 (0.5); 4.0548 (1.0); 4.0384 (1.0); 4.0154 (0.5); 3.9993 (0.5); 3.3353 (62.8); 2.8967 (16.0); 2.8778 (0.4); 2.7893 (11.1); 2.7593 (0.4); 2.7546 (0.4); 2.7374 (13.8); 2.6772 (0.3); 4.68.sup.[a] 2.5477 (0.5); 2.5306 (1.0); 2.5262 (1.5); 2.5128 (40.9); 2.5083 (55.8); 2.5039 (43.2); 2.4798 (4.8); 2.3392 (0.3); 2.3353 (0.5); 2.3309 (0.4); 2.3024 (6.8) I-161 [00207]
.sup.1H-NMR(400.1 MHz, d.sub.6-DMSO): = 9.2344 (2.0); 8.2178 (9.2); 7.9604 (0.4); 7.4490 (0.6); 7.4443 (0.7); 7.4316 (16.0); 7.4249 (4.9); 7.4180 (5.2); 7.3993 (6.0); 7.3581 (3.7); 7.3380 (4.4); 7.3287 (2.5); 7.3235 (3.0); 7.3170 (2.0); 7.3128 (2.0); 7.3093 (2.0); 7.3068 (2.0); 7.3023 (1.6); 7.1076 (4.3); 7.0464 (2.4); 7.0268 (2.2); 4.0561 (1.1); 4.0294 (2.1); 4.0192 (2.1); 3.9923 (1.2); 3.3175 (33.4); 2.8983 (2.6); 2.7393 (2.2); 2.5132 (11.3); 2.5089 (15.5); 2.5045 (12.0); 2.4323 (11.8); 2.2569 (16.0) 4.89.sup.[a] I-162 [00208]
.sup.1H-NMR(600.1 MHz, d.sub.6-DMSO): = 8.9665 (0.6); 8.9571 (1.3); 8.9476 (0.6); 8.5691 (0.2); 8.3604 (1.2); 8.3470 (1.2); 8.3209 (2.1); 8.2497 (6.0); 8.1252 (1.0); 8.1239 (1.0); 8.1121 (1.1); 8.1109 (1.2); 7.9541 (1.4); 7.9143 (0.9); 7.9011 (1.7); 7.8880 (0.8); 7.0627 (1.8); 7.0500 (2.3); 6.9861 (2.1); 6.9529 (1.2); 6.9395 (1.0); 5.9453 (2.6); 3.4750 (0.9); 3.4644 (1.5); 3.4529 (1.4); 3.4506 (1.5); 3.4405 (0.9); 3.3260 (20.8); 2.8913 (12.7); 2.8429 (0.1); 2.8404 (0.2); 2.8241 (1.5); 3.33.sup.[a] 2.8113 (2.2); 2.7993 (1.4); 2.7746 (0.1); 2.7328 (9.9); 2.7319 (10.0); 2.6760 (0.4); 2.6304 (16.0); 2.6181 (0.2); 2.6149 (0.3); 2.6118 (0.2); 2.5240 (0.4); 2.5209 (0.6); 2.5178 (0.5); 2.5090 (9.5); 2.5060 (21.6); 2.5029 (30.6); 2.4998 (22.0); 2.4968 (10.0); 2.3928 (0.1); 2.3899 (0.1); 2.3868 (0.2); 2.3838 (0.1); 2.3009 (0.5); 2.2894 (12.2); 2.2395 (10.5); 2.2296 (0.5); 2.2210 (0.1); 0.0054 (0.4); 0.0001 (14.3); 0.0057 (0.5) I-163 [00209]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.5800 (0.6); 9.5637 (1.2); 9.5475 (0.6); 7.7577 (0.6); 7.7411 (0.8); 7.7368 (1.2); 7.7204 (1.2); 7.7162 (0.9); 7.6996 (0.7); 7.4923 (0.6); 7.4858 (0.6); 7.4693 (1.2); 7.4628 (1.3); 7.4463 (0.7); 7.4397 (0.6); 7.3734 (2.0); 7.3535 (2.4); 7.2590 (0.6); 7.2529 (0.6); 7.2378 (1.1); 7.2318 (1.1); 7.2165 (0.6); 7.2106 (0.5); 7.1442 (2.4); 7.1201 (1.3); 7.1001 (1.2); 4.0860 (0.6); 4.0698 (0.6); 4.0469 (1.4); 4.0305 (1.3); 4.0075 (0.7); 3.9913 (0.7); 3.3312 (32.9); 2.8919 (2.2); 2.7853 (16.0); 2.7332 (1.8); 2.5265 (0.4); 2.5217 (0.5); 2.5130 (8.0); 2.5086 (16.8); 2.5041 (22.6); 2.4996 (16.5); 2.4952 (8.1); 2.4738 (6.3); 2.2987 (8.9) 4.58.sup.[a] I-164 [00210]
.sup.1H-NMR(400.1 MHz, d.sub.6-DMSO): = 9.2353 (2.0); 8.1208 (9.3); 7.4884 (6.0); 7.4836 (2.6); 7.4720 (3.1); 7.4670 (10.4); 7.4608 (2.1); 7.4340 (0.4); 7.4141 (10.2); 7.4051 (11.0); 7.4000 (3.8); 7.3884 (2.8); 7.3836 (6.5); 7.3629 (3.8); 7.3430 (4.3); 7.1131 (4.3); 7.0662 (2.4); 7.0460 (2.2); 4.0550 (1.1); 4.0171 (2.2); 3.9853 (1.2); 3.3172 (25.4); 2.8984 (1.7); 2.7394 (1.4); 2.5132 (11.0); 2.5088 (15.2); 2.5044 (11.7); 2.4353 (11.8); 2.2609 (16.0) 4.91.sup.[a] I-165 [00211]
.sup.1H-NMR(600.1 MHz, d.sub.6-DMSO): = 8.9000 (0.6); 8.8907 (1.2); 8.8813 (0.6); 8.5488 (0.2); 8.3545 (1.1); 8.3411 (1.2); 8.3145 (2.1); 8.2196 (6.0); 8.1208 (1.0); 8.1078 (1.2); 7.9539 (1.3); 7.9105 (0.9); 7.8973 (1.7); 7.8842 (0.8); 7.0737 (1.5); 7.0610 (2.0); 7.0477 (0.1); 7.0294 (2.1); 6.9768 (1.2); 6.9742 (1.2); 6.9642 (1.0); 6.9616 (0.9); 5.9373 (3.2); 3.5107 (0.9); 3.4989 (1.8); 3.4892 (1.8); 3.4772 (1.0); 3.3251 (39.6); 2.8912 (11.3); 2.7887 (1.5); 2.7767 (2.8); 2.7648 (1.4); 3.29.sup.[a] 2.7326 (8.9); 2.7317 (8.8); 2.6391 (0.6); 2.6177 (0.2); 2.6147 (0.3); 2.6115 (0.2); 2.6006 (16.0); 2.5237 (0.4); 2.5206 (0.5); 2.5175 (0.4); 2.5088 (9.2); 2.5057 (21.1); 2.5026 (30.1); 2.4995 (21.7); 2.4965 (9.9); 2.3895 (0.1); 2.3865 (0.2); 2.3834 (0.1); 2.2968 (0.6); 2.2894 (0.1); 2.2089 (11.1); 2.1969 (0.6); 2.1859 (10.2); 2.1754 (0.6); 1.2363 (0.1); 0.0053 (0.3); 0.0001 (12.2); 0.0057 (0.4) I-166 [00212]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.5423 (0.6); 9.5259 (1.3); 9.5096 (0.7); 7.7550 (0.7); 7.7498 (0.7); 7.7355 (0.7); 7.7293 (1.1); 7.7235 (0.8); 7.7090 (0.7); 7.7040 (0.7); 7.6045 (0.7); 7.5832 (1.3); 7.5779 (0.7); 7.5617 (0.9); 7.5565 (1.2); 7.5352 (0.8); 7.4682 (1.0); 7.4650 (1.0); 7.4621 (1.0); 7.4429 (0.8); 7.3703 (2.0); 7.3503 (2.4); 7.1438 (2.6); 7.1215 (1.5); 7.1012 (1.3); 4.2042 (0.4); 4.0722 (0.7); 4.0559 (0.7); 4.0328 (1.5); 4.0166 (1.4); 3.9936 (0.8); 3.9772 (0.7); 3.3218 (92.5); 2.8908 (1.9); 2.7833 (16.0); 2.7316 (1.6); 2.6751 (0.6); 2.6706 (0.8); 2.6662 (0.6); 2.5240 (2.2); 2.5101 (51.7); 2.5061 (100.1); 2.5017 (127.4); 2.4972 (93.8); 2.4673 (7.2); 2.3328 (0.8); 2.3284 (1.0); 2.3240 (0.8); 2.2974 4.65.sup.[a] (9.7); 2.0068 (1.6); 1.2349 (0.4) I-167 [00213]
.sup.1H-NMR(400.1 MHz, d.sub.6-DMSO): = 9.2356 (1.6); 7.8725 (7.0); 7.3844 (2.7); 7.3696 (7.8); 7.3651 (4.0); 7.2648 (3.5); 7.2399 (1.4); 7.2202 (4.3); 7.2066 (3.2); 7.2028 (2.9); 7.1872 (1.1); 7.1829 (1.0); 7.1232 (3.4); 7.0915 (1.9); 7.0716 (1.7); 4.0764 (0.7); 4.0649 (0.8); 4.0389 (1.6); 4.0271 (1.6); 4.0014 (0.9); 3.9892 (0.9); 3.3175 (24.4); 2.8983 (1.6); 2.7393 (1.4); 2.5132 (8.5); 2.5088 (11.8); 2.5045 (9.1); 2.4504 (9.0); 2.4076 (0.4); 2.2693 (12.2); 2.2508 (15.8); 2.2268 (16.0) 5.16.sup.[a] I-168 [00214]
.sup.1H-NMR(600.1 MHz, d.sub.6-DMSO): = 8.9155 (0.6); 8.9062 (1.3); 8.8969 (0.6); 8.5621 (0.2); 8.3562 (1.1); 8.3428 (1.2); 8.3186 (2.1); 8.2355 (6.1); 8.1220 (1.0); 8.1101 (1.1); 8.1089 (1.2); 7.9544 (1.3); 7.9113 (1.0); 7.8982 (1.8); 7.8851 (0.8); 7.3818 (0.4); 7.3775 (3.7); 7.3743 (1.2); 7.3669 (1.6); 7.3635 (5.9); 7.3593 (0.8); 7.3534 (0.2); 7.3203 (0.3); 7.3158 (0.6); 7.3117 (4.8); 7.3083 (1.4); 7.3008 (1.1); 7.2976 (3.1); 7.2934 (0.4); 5.9417 (3.2); 3.5545 (0.9); 3.5428 (2.1); 3.5331 3.09.sup.[a] (2.1); 3.5215 (1.0); 3.3396 (0.1); 3.3259 (35.1); 2.8918 (11.7); 2.8805 (0.1); 2.8655 (1.6); 2.8538 (3.2); 2.8421 (1.5); 2.7329 (9.1); 2.7322 (8.7); 2.6203 (0.5); 2.6154 (0.3); 2.6123 (0.2); 2.5805 (16.0); 2.5244 (0.4); 2.5213 (0.4); 2.5182 (0.4); 2.5094 (9.0); 2.5064 (20.4); 2.5033 (29.0); 2.5002 (20.9); 2.4972 (9.7); 2.4709 (0.1); 2.3903 (0.1); 2.3872 (0.2); 2.3841 (0.1); 2.2994 (0.5); 1.2359 (0.1); 0.0054 (0.3); 0.0001 (10.9); 0.0057 (0.4) I-169 [00215]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.4889 (0.6); 9.4728 (1.3); 9.4567 (0.6); 7.9529 (1.7); 7.3952 (1.1); 7.3744 (4.4); 7.3546 (3.8); 7.1411 (2.5); 7.1269 (2.0); 7.1251 (2.0); 7.1103 (5.0); 7.1066 (4.8); 7.0530 (1.5); 7.0469 (1.3); 7.0327 (1.3); 7.0286 (1.4); 7.0243 (1.1); 4.0783 (0.7); 4.0614 (0.8); 4.0544 (1.5); 4.0371 (5.1); 4.0197 (4.9); 4.0019 (1.9); 3.9836 (0.8); 3.3375 (45.2); 2.8912 (12.5); 2.7675 (16.0); 2.7327 (10.9); 2.5424 (0.7); 2.5256 (0.7); 2.5209 (1.0); 2.5122 (14.3); 2.5078 (29.6); 2.5033 (39.2); 2.4988 (28.2); 2.4945 (13.7); 2.4689 (6.4); 4.81.sup.[a] 2.4299 (1.2); 2.4217 (0.7); 2.4097 (0.8); 2.3298 (0.4); 2.3256 (0.4); 2.3209 (0.3); 2.2936 (10.5); 2.2335 (0.4); 2.2267 (0.5); 1.4068 (0.4); 1.3598 (0.4); 1.3354 (4.3); 1.3179 (9.0); 1.3005 (4.2) I-170 [00216]
.sup.1H-NMR(400.1 MHz, d.sub.6-DMSO): = 9.2342 (1.6); 7.9817 (7.0); 7.9607 (0.6); 7.3844 (7.4); 7.3763 (3.1); 7.3562 (3.2); 7.3474 (1.6); 7.3282 (3.3); 7.3094 (2.6); 7.2636 (3.4); 7.2430 (2.6); 7.2281 (3.0); 7.2106 (1.8); 7.1186 (3.3); 7.0779 (1.9); 7.0581 (1.7); 4.0603 (0.8); 4.0319 (1.6); 4.0221 (1.6); 3.9940 (0.9); 3.3174 (18.8); 2.8983 (3.6); 2.7394 (3.1); 2.5132 (8.2); 2.5089 (11.3); 2.5045 (8.7); 2.4446 (9.0); 2.3091 (16.0); 2.2647 (12.4); 2.2291 (0.5) 4.84.sup.[a] I-171 [00217]
.sup.1H-NMR(600.1 MHz, d.sub.6-DMSO): = 8.9710 (0.6); 8.9615 (1.3); 8.9519 (0.6); 8.5641 (0.3); 8.4809 (0.1); 8.3569 (1.1); 8.3436 (1.2); 8.3178 (2.1); 8.2444 (6.0); 8.1251 (1.0); 8.1239 (1.0); 8.1121 (1.1); 8.1109 (1.2); 7.9543 (1.5); 7.9142 (0.9); 7.9011 (1.7); 7.8880 (0.8); 7.4682 (0.1); 7.4642 (0.1); 7.2797 (2.3); 7.2783 (2.3); 7.2661 (2.2); 7.2532 (2.6); 7.1241 (1.2); 7.1225 (1.3); 7.1112 (1.1); 7.1097 (1.1); 5.9443 (1.6); 3.5533 (0.9); 3.5417 (1.9); 3.5319 (2.0); 3.5202 (0.9); 3.3258 3.36.sup.[a] (14.3); 2.9535 (1.6); 2.9417 (3.0); 2.9299 (1.4); 2.8916 (13.2); 2.7748 (0.1); 2.7330 (10.4); 2.7321 (10.4); 2.6680 (0.6); 2.6220 (16.0); 2.6124 (0.3); 2.6091 (0.1); 2.5243 (0.5); 2.5212 (0.6); 2.5180 (0.6); 2.5093 (10.2); 2.5063 (22.8); 2.5032 (32.3); 2.5001 (23.1); 2.4971 (10.4); 2.3903 (0.2); 2.3871 (0.2); 2.3840 (0.1); 2.3007 (0.8); 2.2871 (10.8); 2.2763 (0.6); 2.2610 (0.2); 2.2393 (0.1); 0.0054 (0.4); 0.0001 (13.1); 0.0057 (0.4) I-172 [00218]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.5701 (0.6); 9.5538 (1.3); 9.5378 (0.6); 8.2988 (0.5); 8.2923 (4.6); 8.2874 (1.6); 8.2751 (1.5); 8.2701 (5.2); 8.2638 (0.6); 7.9532 (0.4); 7.8680 (0.6); 7.8616 (5.0); 7.8568 (1.7); 7.8444 (1.5); 7.8394 (4.6); 7.8330 (0.5); 7.3718 (2.1); 7.3518 (2.4); 7.1417 (2.6); 7.1156 (1.4); 7.0956 (1.2); 4.0828 (0.6); 4.0664 (0.6); 4.0438 (1.4); 4.0274 (1.4); 4.0043 (0.7); 3.9882 (0.7); 3.3255 (30.7); 2.8913 (2.9); 2.7999 (16.0); 2.7846 (0.4); 2.7324 (2.5); 2.5421 (0.3); 2.5253 (0.7); 2.5205 (1.0); 2.5116 (12.6); 2.5074 (25.8); 2.5029 (34.1); 2.4985 (25.0); 2.4696 (6.6); 2.2922 (9.5) 4.42.sup.[a] I-173 [00219]
.sup.1H-NMR(400.1 MHz, d.sub.6-DMSO): = 9.2464 (2.2); 8.2401 (8.4); 7.9603 (2.1); 7.6163 (2.9); 7.6131 (3.0); 7.5962 (3.5); 7.5929 (3.4); 7.5062 (8.7); 7.3390 (2.9); 7.3262 (4.0); 7.3190 (5.9); 7.3064 (4.4); 7.2990 (3.4); 7.0985 (7.7); 7.0956 (7.7); 7.0788 (3.4); 7.0755 (3.2); 7.0124 (2.6); 6.9932 (2.3); 4.0537 (1.1); 4.0414 (1.2); 4.0173 (2.3); 4.0046 (2.3); 3.9807 (1.3); 3.9671 (1.2); 3.3172 (40.4); 3.2725 (0.4); 2.8982 (13.4); 2.7389 (11.7); 2.5639 (0.3); 2.5129 (14.0); 2.5086 (18.0); 2.5043 (13.6); 2.4629 (0.6); 2.4111 (12.1); 2.3332 (0.5); 2.2617 (16.0); 2.2190 (0.6) 5.10.sup.[a] I-174 [00220]
.sup.1H-NMR(600.1 MHz, d.sub.6-DMSO): = 8.9390 (0.4); 8.9296 (0.9); 8.9203 (0.4); 8.3189 (0.9); 8.3051 (1.0); 8.2966 (1.6); 8.2215 (4.6); 8.1447 (0.8); 8.1436 (0.8); 8.1317 (0.8); 8.1305 (0.9); 7.9549 (0.5); 7.9207 (0.7); 7.9076 (1.3); 7.8945 (0.6); 7.3369 (0.9); 7.3343 (0.4); 7.3243 (2.4); 7.3151 (0.7); 7.3123 (2.2); 7.2865 (2.1); 7.2841 (2.7); 7.2728 (1.5); 7.2492 (0.5); 7.2469 (0.8); 7.2446 (0.4); 7.2349 (1.2); 7.2317 (0.3); 7.2252 (0.3); 7.2229 (0.5); 7.2206 (0.2); 3.5682 (0.7); 3.5564 (1.5); 3.5467 (1.5); 3.5348 (0.8); 3.3259 (29.1); 2.8919 (4.8); 2.8819 (1.3); 3.15.sup.[a] 2.8699 (2.4); 2.8580 (1.2); 2.7688 (16.0); 2.7334 (3.8); 2.7325 (3.8); 2.6157 (0.2); 2.6126 (0.1); 2.5972 (12.2); 2.5247 (0.3); 2.5216 (0.3); 2.5185 (0.3); 2.5098 (6.0); 2.5067 (13.5); 2.5037 (19.0); 2.5006 (13.6); 2.4975 (6.1); 2.3876 (0.1); 0.0054 (0.2); 0.0001 (8.2); 0.0057 (0.2) I-175 [00221]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.5097 (0.6); 9.4939 (1.3); 9.4779 (0.6); 7.9524 (0.5); 7.6219 (2.7); 7.6188 (3.1); 7.4765 (0.8); 7.4565 (3.8); 7.4497 (3.1); 7.4459 (3.1); 7.4300 (0.6); 7.4262 (0.7); 7.3715 (2.0); 7.3516 (2.4); 7.1411 (2.6); 7.1177 (1.4); 7.0975 (1.2); 4.0751 (0.6); 4.0589 (0.6); 4.0362 (1.4); 4.0199 (1.4); 3.9967 (0.8); 3.9806 (0.7); 3.3283 (30.3); 2.8908 (3.3); 2.7723 (16.0); 2.7316 (2.9); 2.5250 (0.6); 2.5203 (0.9); 2.5112 (13.2); 2.5071 (28.2); 2.5027 (38.6); 2.4982 (29.5); 2.4682 (6.7); 2.3877 (12.4); 2.3293 (0.5); 2.2947 (9.4); 1.3365 (0.7); 1.2989 (0.4); 1.2585 (0.8); 1.2331 (0.4) 5.29.sup.[a] I-176 [00222]
.sup.1H-NMR(400.1 MHz, d.sub.6-DMSO): = 9.3094 (2.0); 8.1043 (8.1); 7.9605 (0.7); 7.6840 (1.3); 7.6801 (1.4); 7.6631 (2.6); 7.6464 (1.5); 7.6424 (1.5); 7.4944 (9.3); 7.3919 (1.2); 7.3881 (1.3); 7.3720 (2.9); 7.3685 (2.1); 7.3555 (5.3); 7.3353 (4.0); 7.2929 (2.3); 7.2744 (3.5); 7.2729 (3.5); 7.2528 (1.4); 7.1067 (4.4); 7.0461 (2.4); 7.0256 (2.1); 4.0598 (1.0); 4.0306 (2.1); 3.9937 (1.1); 3.3173 (38.1); 2.8981 (4.9); 2.7388 (4.2); 2.5130 (11.8); 2.5086 (16.0); 2.5042 (11.9); 2.4351 (11.6); 2.2712 (0.3); 2.2487 (16.0); 2.2222 (0.3) 4.86.sup.[a] I-177 [00223]
.sup.1H-NMR(600.1 MHz, d.sub.6-DMSO): = 8.8598 (0.6); 8.8519 (1.0); 8.8444 (0.6); 8.8409 (0.5); 8.3181 (0.1); 8.3059 (1.5); 8.2904 (2.2); 8.2863 (2.7); 8.1390 (1.4); 8.1297 (4.7); 8.1266 (5.6); 7.9547 (1.3); 7.9156 (1.2); 7.9025 (2.2); 7.8895 (1.0); 7.3415 (1.5); 7.3389 (0.7); 7.3285 (4.2); 7.3197 (1.1); 7.3167 (3.9); 7.2981 (3.8); 7.2957 (4.9); 7.2843 (2.4); 7.2459 (0.8); 7.2436 (1.3); 7.2413 (0.7); 7.2317 (2.1); 7.2221 (0.5); 7.2198 (0.8); 7.2175 (0.4); 3.5513 (0.5); 3.5403 (0.6); 3.5383 (0.6); 3.5290 (0.9); 3.5184 (0.8); 3.5163 (0.9); 3.5053 (0.8); 3.4458 (0.5); 3.39.sup.[a] 3.4436 (0.5); 3.4370 (0.6); 3.4346 (1.0); 3.4236 (0.9); 3.4151 (0.4); 3.4126 (0.6); 3.4101 (0.4); 3.4036 (0.4); 3.4015 (0.4); 3.3260 (48.3); 3.0728 (0.1); 3.0612 (0.5); 3.0493 (1.0); 3.0373 (1.0); 3.0254 (0.5); 3.0132 (0.1); 2.8919 (11.3); 2.7751 (0.1); 2.7714 (0.3); 2.7600 (16.0); 2.7584 (16.0); 2.7333 (8.8); 2.7324 (9.0); 2.7197 (0.2); 2.6188 (0.2); 2.6156 (0.3); 2.6125 (0.2); 2.5245 (0.8); 2.5195 (10.8); 2.5134 (11.2); 2.5097 (11.6); 2.5066 (25.1); 2.5036 (35.2); 2.5005 (25.2); 2.4974 (11.4); 2.3905 (0.2); 2.3874 (0.2); 2.3844 (0.2); 1.2719 (8.5); 1.2603 (8.5); 0.0054 (0.4); 0.0001 (14.9); 0.0057 (0.5) I-178 [00224]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.5563 (0.7); 9.5402 (1.4); 9.5235 (0.7); 8.1436 (1.8); 8.1230 (2.0); 8.0905 (1.8); 8.0697 (2.0); 8.0572 (1.9); 8.0372 (2.0); 7.9524 (0.6); 7.9239 (2.1); 7.9062 (2.4); 7.6259 (1.7); 7.6060 (3.0); 7.5878 (2.9); 7.5723 (1.2); 7.5696 (1.4); 7.5452 (1.4); 7.5276 (1.6); 7.5247 (1.5); 7.5101 (0.7); 7.5074 (0.8); 7.4066 (2.2); 7.3867 (2.5); 7.1561 (2.8); 7.1360 (1.6); 7.1156 (1.4); 4.1353 (0.7); 4.1192 (0.7); 4.0965 (1.6); 4.0801 (1.5); 4.0572 (0.8); 4.0410 (0.8); 3.3251 (29.5); 2.8893 (3.5); 2.7310 (3.2); 2.7050 (16.0); 2.5413 (0.3); 2.5240 (0.7); 2.5060 (32.0); 2.5018 (45.8); 2.4977 (37.5); 2.3287 (0.3); 2.2895 (10.2) 4.99.sup.[a] I-179 [00225]
.sup.1H-NMR(400.1 MHz, d.sub.6-DMSO): = 9.2403 (0.9); 9.2272 (0.4); 8.0469 (4.3); 7.3960 (4.4); 7.3706 (2.0); 7.3610 (0.4); 7.3510 (2.7); 7.3341 (0.4); 7.3293 (1.0); 7.1158 (1.8); 7.0706 (1.0); 7.0506 (0.9); 6.9949 (0.9); 6.9890 (1.5); 6.9858 (1.0); 6.9814 (1.8); 6.9724 (2.7); 6.9691 (4.8); 6.9656 (2.4); 5.7609 (3.1); 4.0731 (0.4); 4.0607 (0.4); 4.0361 (0.9); 4.0228 (0.8); 3.9984 (0.4); 3.9853 (0.4); 3.7578 (16.0); 3.3197 (11.4); 2.5175 (1.6); 2.5131 (3.4); 2.5086 (4.8); 2.5041 (3.4); 2.4997 (1.6); 2.4421 (5.0); 2.2652 (7.0); 1.0644 (0.4) 4.59.sup.[a] I-180 [00226]
.sup.1H-NMR(600.1 MHz, d.sub.6-DMSO): = 8.9750 (0.5); 8.9656 (1.0); 8.9561 (0.5); 8.3229 (0.9); 8.3093 (1.0); 8.2986 (1.7); 8.2384 (4.8); 8.1462 (0.8); 8.1332 (1.0); 7.9547 (0.8); 7.9237 (0.7); 7.9106 (1.3); 7.8975 (0.6); 7.0684 (1.5); 7.0556 (1.8); 6.9909 (1.7); 6.9820 (0.2); 6.9567 (1.0); 6.9440 (0.8); 3.4809 (0.7); 3.4701 (1.2); 3.4567 (1.2); 3.4465 (0.7); 3.3251 (27.1); 2.8919 (7.0); 2.8852 (0.1); 2.8325 (1.2); 2.8198 (1.8); 2.8077 (1.2); 2.7721 (16.0); 2.7555 (0.1); 2.7332 (5.5); 2.7325 (5.3); 2.6492 (12.7); 2.6184 (0.1); 2.6155 (0.3); 2.6124 (0.2); 2.5245 (0.3); 3.80.sup.[a] 2.5214 (0.4); 2.5183 (0.3); 2.5095 (7.2); 2.5065 (16.0); 2.5034 (22.7); 2.5004 (16.4); 2.4973 (7.6); 2.3873 (0.1); 2.3843 (0.1); 2.2942 (9.7); 2.2703 (0.1); 2.2424 (8.6); 2.2359 (0.9); 2.2206 (0.6); 1.1709 (0.1); 0.0054 (0.2); 0.0001 (7.5); 0.0057 (0.2) I-181 [00227]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.5305 (0.7); 9.5145 (1.4); 9.4980 (0.7); 8.2245 (3.0); 7.9947 (2.7); 7.9819 (3.2); 7.9728 (2.9); 7.9660 (1.8); 7.9615 (1.7); 7.9538 (1.8); 7.6420 (0.5); 7.6384 (0.6); 7.6249 (1.5); 7.6213 (1.4); 7.6062 (2.6); 7.6019 (1.7); 7.5913 (1.4); 7.5878 (1.5); 7.5779 (2.0); 7.5739 (2.3); 7.5566 (1.7); 7.5524 (1.8); 7.3906 (2.2); 7.3708 (2.6); 7.1506 (2.7); 7.1308 (1.6); 7.1105 (1.5); 4.1016 (0.7); 4.0854 (0.7); 4.0624 (1.6); 4.0460 (1.5); 4.0231 (0.8); 4.0070 (0.8); 3.3266 (28.0); 2.8900 (10.2); 2.7621 (16.0); 2.7318 (9.3); 2.5421 (0.5); 5.08.sup.[a] 2.5249 (0.6); 2.5070 (29.2); 2.5027 (39.2); 2.4984 (29.4); 2.4842 (7.6); 2.4487 (0.4); 2.4211 (0.4); 2.4045 (0.3); 2.3294 (0.3); 2.2965 (10.2) I-182 [00228]
.sup.1H-NMR(400.1 MHz, d.sub.6-DMSO): = 9.2932 (1.1); 9.2782 (2.4); 9.2633 (1.3); 8.0660 (10.9); 7.9784 (4.2); 7.9651 (2.6); 7.9574 (6.1); 7.9505 (3.1); 7.9397 (2.5); 7.9308 (2.0); 7.9242 (2.2); 7.9158 (2.4); 7.6053 (1.1); 7.5964 (5.4); 7.5883 (4.6); 7.5809 (4.5); 7.5727 (5.2); 7.5641 (1.2); 7.4322 (11.6); 7.4129 (3.0); 7.4084 (3.0); 7.3713 (3.6); 7.3514 (4.1); 7.1098 (4.3); 7.0510 (2.4); 7.0311 (2.2); 4.0775 (1.1); 4.0620 (1.2); 4.0401 (2.5); 4.0250 (2.5); 4.0027 (1.4); 3.9876 (1.3); 3.3188 5.11.sup.[a] (45.3); 2.8979 (5.2); 2.7392 (4.5); 2.5132 (12.4); 2.5088 (17.0); 2.5045 (13.1); 2.4413 (11.9); 2.3937 (0.5); 2.2576 (0.4); 2.2357 (16.0) I-183 [00229]
.sup.1H-NMR(600.1 MHz, d.sub.6-DMSO): = 8.9101 (0.5); 8.9008 (0.9); 8.8914 (0.5); 8.3168 (0.8); 8.3030 (1.0); 8.2923 (1.6); 8.2085 (4.5); 8.1446 (0.7); 8.1435 (0.8); 8.1316 (0.8); 8.1304 (0.9); 7.9545 (0.7); 7.9203 (0.7); 7.9072 (1.2); 7.8940 (0.6); 7.0785 (1.1); 7.0657 (1.4); 7.0356 (1.6); 6.9829 (0.9); 6.9806 (0.9); 6.9703 (0.7); 6.9678 (0.7); 3.5147 (0.6); 3.5030 (1.4); 3.4932 (1.4); 3.4813 (0.7); 3.3250 (27.1); 2.8917 (5.9); 2.7970 (1.1); 2.7850 (2.1); 2.7730 (1.2); 2.7648 (16.0); 2.7332 3.76.sup.[a] (4.6); 2.7323 (4.8); 2.6215 (12.1); 2.6124 (0.2); 2.5243 (0.3); 2.5212 (0.4); 2.5181 (0.3); 2.5094 (6.7); 2.5063 (15.2); 2.5033 (21.8); 2.5002 (15.7); 2.4971 (7.2); 2.3873 (0.2); 2.2553 (0.2); 2.2141 (8.4); 2.1893 (7.8); 2.1689 (0.3); 0.0054 (0.2); 0.0001 (8.2); 0.0057 (0.3) I-184 [00230]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.6078 (0.6); 9.5916 (1.3); 9.5752 (0.6); 7.9536 (0.4); 7.8091 (0.7); 7.8053 (0.8); 7.7882 (1.5); 7.7714 (0.8); 7.7675 (0.9); 7.6779 (0.7); 7.6742 (0.8); 7.6586 (1.6); 7.6551 (1.0); 7.6430 (0.9); 7.6392 (0.8); 7.3737 (3.2); 7.3539 (4.5); 7.3343 (1.0); 7.1456 (2.5); 7.1206 (1.4); 7.1002 (1.2); 4.0877 (0.6); 4.0712 (0.6); 4.0484 (1.4); 4.0320 (1.3); 4.0091 (0.7); 3.9927 (0.7); 3.3317 (59.0); 2.8916 (3.0); 2.7944 (16.0); 2.7327 (2.6); 2.5258 (0.5); 2.5212 (0.8); 2.5124 (11.9); 2.5081 (24.4); 2.5036 (32.4); 2.4991 (23.4); 2.4948 (11.3); 2.4747 (6.5); 2.2983 (9.2) 4.90.sup.[a] I-185 [00231]
.sup.1H-NMR(400.1 MHz, d.sub.6-DMSO): = 9.2337 (2.1); 8.0518 (9.3); 7.9606 (1.0); 7.3928 (9.5); 7.3707 (3.7); 7.3518 (5.2); 7.3330 (4.7); 7.3134 (3.0); 7.1165 (4.3); 7.0694 (2.5); 7.0494 (2.2); 6.9754 (5.3); 6.9703 (6.6); 6.9554 (4.4); 6.9504 (5.9); 6.9346 (4.2); 6.9302 (4.9); 6.9252 (2.8); 4.0603 (1.1); 4.0446 (2.7); 4.0272 (8.6); 4.0098 (7.5); 3.9925 (3.5); 3.3176 (40.3); 3.2770 (0.4); 2.8984 (6.4); 2.7394 (5.6); 2.5133 (12.3); 2.5089 (16.9); 2.5045 (13.0); 2.4414 (11.8); 2.2659 (16.0); 1.3265 (6.9); 1.3091 (14.7); 1.2917 (7.2) 4.89.sup.[a] I-186 [00232]
.sup.1H-NMR(600.1 MHz, d.sub.6-DMSO): = 8.9825 (0.5); 8.9729 (1.0); 8.9633 (0.5); 8.3198 (0.8); 8.3060 (1.0); 8.2953 (1.6); 8.2365 (4.5); 8.1475 (0.7); 8.1463 (0.8); 8.1344 (0.8); 8.1332 (0.9); 7.9548 (0.8); 7.9237 (0.7); 7.9106 (1.3); 7.8975 (0.6); 7.2854 (1.6); 7.2841 (1.7); 7.2738 (1.6); 7.2609 (1.9); 7.2414 (0.2); 7.1777 (0.2); 7.1649 (0.2); 7.1281 (0.9); 7.1265 (0.9); 7.1152 (0.8); 7.1136 (0.8); 3.5580 (0.6); 3.5465 (1.4); 3.5365 (1.5); 3.5249 (0.7); 3.3261 (22.7); 3.2035 (0.1); 3.1907 3.84.sup.[a] (0.1); 2.9614 (1.1); 2.9497 (2.2); 2.9379 (1.1); 2.8922 (7.4); 2.8845 (0.1); 2.7715 (16.0); 2.7573 (0.2); 2.7453 (0.2); 2.7335 (5.9); 2.7326 (5.9); 2.6542 (0.1); 2.6408 (12.0); 2.6190 (0.1); 2.6158 (0.2); 2.6128 (0.1); 2.5249 (0.3); 2.5218 (0.4); 2.5187 (0.4); 2.5099 (7.4); 2.5069 (16.7); 2.5038 (23.6); 2.5007 (16.8); 2.4977 (7.5); 2.3908 (0.1); 2.3876 (0.1); 2.3847 (0.1); 2.2903 (8.1); 2.2800 (0.2); 2.2685 (0.8); 0.0054 (0.2); 0.0001 (7.3); 0.0057 (0.2) I-187 [00233]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.5408 (0.7); 9.5249 (1.4); 9.5088 (0.7); 7.9525 (0.7); 7.8571 (1.5); 7.8521 (1.6); 7.8394 (1.6); 7.8344 (1.6); 7.6293 (0.6); 7.6242 (0.6); 7.6175 (0.8); 7.6122 (0.9); 7.6082 (1.3); 7.6031 (1.3); 7.5962 (1.3); 7.5910 (1.2); 7.5676 (1.9); 7.5448 (2.5); 7.5230 (1.0); 7.3713 (2.1); 7.3514 (2.5); 7.1437 (2.9); 7.1209 (1.6); 7.1008 (1.4); 4.0736 (0.7); 4.0571 (0.8); 4.0345 (1.6); 4.0183 (1.6); 3.9950 (0.8); 3.9788 (0.8); 3.3235 (54.8); 2.8908 (4.6); 2.7829 (16.0); 2.7315 (4.0); 2.6754 (0.4); 2.6709 (0.5); 2.6664 (0.4); 2.5243 (1.3); 2.5106 (32.0); 2.5064 (62.6); 2.5020 (80.2); 2.4976 (62.1); 2.4685 (7.8); 2.3332 (0.6); 2.3289 (0.7); 2.3245 (0.6); 2.2976 (10.3) 4.98.sup.[a] I-188 [00234]
.sup.1H-NMR(400.1 MHz, d.sub.6-DMSO): = 9.2468 (1.2); 9.2313 (2.5); 9.2161 (1.3); 8.2978 (9.4); 7.6475 (5.1); 7.6264 (5.8); 7.5932 (5.4); 7.5878 (5.7); 7.4538 (9.6); 7.3525 (3.5); 7.3325 (4.0); 7.3067 (3.2); 7.3014 (3.2); 7.2857 (2.9); 7.2803 (2.9); 7.1054 (4.3); 7.0403 (2.4); 7.0207 (2.2); 4.0662 (1.1); 4.0508 (1.2); 4.0290 (2.6); 4.0135 (2.6); 3.9916 (1.4); 3.9761 (1.4); 3.3170 (25.0); 2.8984 (1.1); 2.7392 (1.0); 2.5131 (11.3); 2.5088 (15.4); 2.5045 (11.7); 2.4272 (11.7); 2.2565 (16.0); 2.2193 (0.5) 5.31.sup.[a] I-189 [00235]
.sup.1H-NMR(600.1 MHz, d.sub.6-DMSO): = 9.4364 (0.4); 9.4262 (0.9); 9.4159 (0.4); 8.3212 (0.9); 8.3074 (1.1); 8.2994 (1.6); 8.1954 (4.6); 8.1490 (0.8); 8.1478 (0.8); 8.1347 (0.9); 7.9550 (1.2); 7.9244 (0.7); 7.9113 (1.3); 7.8982 (0.6); 7.4939 (1.5); 7.4798 (2.1); 7.4669 (1.3); 7.4642 (1.4); 7.4075 (0.9); 7.4043 (0.8); 7.3935 (0.6); 7.3903 (0.6); 4.1447 (0.4); 4.1346 (0.4); 4.1199 (0.9); 4.1096 (0.8); 4.0951 (0.4); 4.0847 (0.4); 3.3297 (64.3); 2.8926 (10.3); 2.7733 (16.0); 2.7338 (8.0); 2.7329 (8.2); 2.6194 (0.1); 2.6164 (0.2); 2.6133 (0.1); 2.5370 (12.1); 2.5254 (0.4); 2.5223 (0.4); 2.5192 (0.4); 2.5104 (8.0); 2.5074 (18.9); 2.5043 (28.4); 2.5013 (22.0); 2.4982 (10.6); 2.3913 (0.1); 2.3882 (0.2); 2.3852 (0.1); 0.9132 (0.1); 0.0054 (0.2); 0.0001 (7.7); 0.0057 (0.3) 4.10.sup.[a] I-190 [00236]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.5059 (0.6); 9.4901 (1.2); 9.4743 (0.6); 8.3115 (0.4); 7.9519 (0.5); 7.6404 (0.4); 7.6333 (4.0); 7.6282 (1.6); 7.6114 (4.7); 7.5361 (1.5); 7.3725 (2.0); 7.3520 (5.3); 7.2884 (3.9); 7.2668 (3.5); 7.1676 (1.6); 7.1425 (2.5); 7.1205 (1.4); 7.1005 (1.3); 4.0766 (0.7); 4.0599 (0.7); 4.0373 (1.4); 4.0209 (1.4); 3.9980 (0.8); 3.9819 (0.7); 3.7836 (0.3); 3.7728 (0.3); 3.3346 (60.4); 3.3239 (91.1); 2.8913 (3.6); 2.7658 (16.0); 2.7489 (0.4); 2.7328 (3.1); 2.7317 (3.1); 2.6752 (0.6); 2.6709 (0.8); 2.6665 (0.6); 2.5412 (0.5); 2.5241 (2.4); 2.5063 (99.7); 2.5019 (127.0); 2.4974 (93.2); 2.4932 (46.4); 2.4695 (6.9); 2.3329 (0.7); 2.3287 (0.9); 2.3242 (0.7); 2.2962 (9.4); 1.2358 (0.7); 0.0002 (0.4) 4.62.sup.[a] I-191 [00237]
.sup.1H-NMR(400.1 MHz, d.sub.6-DMSO): = 9.1895 (1.4); 9.1747 (2.6); 9.1595 (1.4); 8.5251 (7.4); 8.3750 (2.8); 8.3650 (2.8); 7.7328 (1.4); 7.7283 (1.4); 7.7132 (2.7); 7.7095 (2.6); 7.6941 (1.6); 7.6896 (1.5); 7.4108 (7.9); 7.3167 (3.3); 7.2968 (3.7); 7.2372 (2.2); 7.2182 (5.7); 7.2064 (2.6); 7.1979 (3.6); 7.0918 (4.6); 7.0201 (2.6); 7.0007 (2.3); 5.7613 (0.6); 4.0190 (1.3); 4.0034 (1.4); 3.9817 (2.8); 3.9663 (2.7); 3.9443 (1.5); 3.9290 (1.4); 3.3175 (18.3); 2.5084 (17.4); 2.3941 (12.3); 2.3348 (0.4); 2.2708 (16.0); 2.2335 (0.4); 2.0804 (5.1) 3.85.sup.[a] I-192 [00238]
.sup.1H-NMR(600.1 MHz, d.sub.6-DMSO): = 9.3981 (0.5); 9.3877 (1.0); 9.3771 (0.5); 8.3145 (0.9); 8.2988 (1.3); 8.2944 (1.6); 8.2004 (4.6); 8.1453 (0.8); 8.1323 (0.9); 7.9548 (1.4); 7.9511 (1.9); 7.9479 (1.9); 7.9219 (0.7); 7.9089 (1.2); 7.8958 (0.6); 7.7335 (0.9); 7.7303 (0.9); 7.7194 (1.2); 7.7162 (1.2); 7.5837 (2.2); 7.5695 (1.9); 4.2758 (0.4); 4.2653 (0.4); 4.2521 (0.9); 4.2416 (0.9); 4.2283 (0.5); 4.2177 (0.4); 3.3293 (9.1); 2.8926 (11.6); 2.8823 (0.1); 2.7692 (16.0); 2.7337 (9.0); 2.7328 (9.1); 2.6191 (0.1); 2.6160 (0.2); 2.6130 (0.1); 2.5252 (0.4); 2.5220 (0.5); 2.5189 (0.4); 2.5102 (8.5); 2.5071 (20.2); 2.5042 (35.5); 2.5010 (20.0); 2.4980 (9.2); 2.3910 (0.1); 2.3879 (0.2); 2.3849 (0.1); 0.0053 (0.2); 0.0001 (8.3); 0.0057 (0.3) 4.18.sup.[a] I-193 [00239]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.5590 (0.7); 9.5431 (1.4); 9.5269 (0.7); 7.9521 (1.2); 7.7637 (1.4); 7.7622 (1.4); 7.7591 (3.1); 7.7546 (2.1); 7.6834 (6.7); 7.6818 (5.7); 7.6788 (6.7); 7.3693 (2.2); 7.3494 (2.6); 7.1416 (2.8); 7.1156 (1.6); 7.0957 (1.4); 4.0726 (0.7); 4.0565 (0.7); 4.0334 (1.5); 4.0172 (1.5); 3.9942 (0.8); 3.9777 (0.8); 3.3274 (43.7); 2.8906 (8.3); 2.7983 (16.0); 2.7485 (0.5); 2.7313 (7.8); 2.5418 (0.4); 2.5241 (0.8); 2.5066 (36.8); 2.5023 (50.2); 2.4980 (38.7); 2.4672 (7.2); 2.3290 (0.5); 2.3246 (0.4); 2.2959 (10.2) 5.53.sup.[a] I-194 [00240]
.sup.1H-NMR(400.1 MHz, d.sub.6-DMSO): = 9.2138 (0.7); 9.1982 (1.6); 9.1832 (0.8); 8.5155 (5.9); 7.9607 (0.5); 7.6126 (1.5); 7.5932 (3.2); 7.5739 (1.9); 7.4068 (6.2); 7.3251 (2.3); 7.3051 (2.6); 7.0989 (4.4); 7.0808 (2.6); 7.0641 (0.4); 7.0270 (1.6); 7.0070 (1.4); 6.9558 (2.4); 6.9359 (2.3); 4.0286 (0.7); 4.0130 (0.8); 3.9914 (1.6); 3.9762 (1.6); 3.9536 (1.0); 3.9388 (0.9); 3.3183 (31.6); 2.8983 (3.5); 2.7392 (3.1); 2.5131 (7.7); 2.5088 (10.4); 2.5045 (7.9); 2.4883 (1.3); 2.4007 (7.6); 2.3769 (16.0); 2.3358 (0.5); 2.2724 (10.4); 2.2533 (1.0) 4.40.sup.[a] I-195 [00241]
.sup.1H-NMR(600.1 MHz, d.sub.6-DMSO): = 9.3965 (0.8); 9.3860 (1.6); 9.3755 (0.8); 8.5262 (0.2); 8.3580 (1.3); 8.3446 (1.4); 8.3188 (2.4); 8.1849 (6.8); 8.1286 (1.2); 8.1274 (1.2); 8.1156 (1.3); 8.1144 (1.4); 7.9542 (1.8); 7.9174 (1.1); 7.9042 (2.0); 7.8911 (0.9); 7.3690 (0.1); 7.3578 (2.2); 7.3446 (2.5); 7.1427 (2.4); 7.1258 (1.3); 7.1124 (1.2); 5.9634 (4.0); 4.1093 (0.6); 4.0987 (0.7); 4.0841 (1.5); 4.0735 (1.4); 4.0589 (0.7); 4.0485 (0.6); 3.3551 (0.2); 3.3255 (40.9); 2.8914 (16.0); 2.7329 (12.2); 2.7320 (12.4); 2.6181 (0.2); 2.6151 (0.3); 2.6121 (0.2); 2.5733 (0.5); 2.5521 (0.1); 2.5489 (0.1); 2.5459 (0.1); 2.5307 (17.6); 2.5243 (1.1); 2.5210 (0.9); 2.5179 (0.9); 2.5091 (11.2); 2.5061 (24.1); 2.5030 (33.6); 2.5000 (24.1); 2.4969 (11.1); 2.4777 (0.1); 2.4751 (0.1); 2.4514 (6.6); 2.4210 (0.1); 2.3901 (0.2); 2.3869 (0.2); 2.3838 (0.2); 2.3095 (9.6); 2.2998 (0.9); 0.0053 (0.3); 0.0001 (11.4); 0.0057 (0.4) 3.52.sup.[a] I-196 [00242]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.5966 (0.6); 9.5807 (1.2); 9.5648 (0.6); 7.9536 (1.8); 7.8583 (2.9); 7.8527 (2.9); 7.7798 (3.1); 7.7590 (3.8); 7.5617 (2.0); 7.5561 (1.9); 7.5409 (1.6); 7.5353 (1.6); 7.3702 (2.0); 7.3502 (2.3); 7.1442 (2.3); 7.1183 (1.3); 7.0984 (1.1); 4.0846 (0.6); 4.0681 (0.6); 4.0455 (1.3); 4.0290 (1.3); 4.0062 (0.7); 3.9899 (0.6); 3.3241 (30.0); 2.8912 (13.6); 2.8728 (0.4); 2.7912 (16.0); 2.7500 (0.4); 2.7326 (11.4); 2.5420 (0.4); 2.5251 (0.7); 2.5203 (1.1); 2.5117 (14.1); 2.5073 (28.2); 2.5028 (36.4); 2.4982 (25.6); 2.4937 (11.9); 2.4724 (6.1); 2.3297 (0.4); 2.2976 (8.7) 5.26.sup.[a] I-197 [00243]
.sup.1H-NMR(600.1 MHz, d.sub.6-DMSO): = 9.3407 (0.8); 9.3303 (1.7); 9.3200 (0.8); 8.5552 (0.2); 8.3581 (1.4); 8.3447 (1.5); 8.3177 (2.6); 8.2051 (7.2); 8.1262 (1.2); 8.1250 (1.3); 8.1120 (1.4); 7.9540 (1.8); 7.9143 (1.2); 7.9011 (2.1); 7.8880 (1.0); 7.3511 (2.6); 7.3021 (0.5); 7.2993 (0.4); 7.2887 (2.6); 7.2858 (3.2); 7.2828 (4.0); 7.2694 (0.6); 5.9610 (4.2); 4.0843 (0.7); 4.0739 (0.7); 4.0598 (1.6); 4.0493 (1.6); 4.0351 (0.8); 4.0247 (0.7); 3.3249 (33.8); 2.8913 (16.0); 2.7328 (12.0); 2.7319 (12.7); 2.6181 (0.2); 2.6150 (0.3); 2.6118 (0.2); 2.5803 (0.5); 2.5589 (0.1); 2.5437 (18.9); 2.5240 (0.5); 2.5209 (0.6); 2.5178 (0.6); 2.5090 (11.0); 2.5060 (24.9); 2.5029 (35.5); 2.4998 (25.7); 2.4968 (12.0); 2.3900 (0.2); 2.3868 (0.2); 2.3837 (0.2); 2.2970 (0.7); 2.2873 (13.6); 2.2791 (0.8); 2.2695 (10.2); 1.2360 (0.2); 0.8538 (0.1); 0.0054 (0.3); 0.0001 (12.8); 0.0057 (0.4) 3.46.sup.[a] I-198 [00244]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.6080 (0.4); 9.5917 (0.8); 9.5748 (0.4); 8.9830 (0.4); 7.9521 (2.4); 7.8630 (1.7); 7.8569 (1.9); 7.7087 (1.3); 7.6872 (2.4); 7.6410 (1.4); 7.6348 (1.3); 7.6195 (0.8); 7.6132 (0.8); 7.3699 (1.2); 7.3499 (1.4); 7.1451 (1.5); 7.1168 (0.8); 7.0971 (0.7); 4.0832 (0.4); 4.0662 (0.4); 4.0444 (0.8); 4.0278 (0.8); 4.0045 (0.4); 3.9885 (0.4); 3.3210 (56.7); 2.8905 (16.0); 2.8708 (0.9); 2.7980 (9.0); 2.7473 (0.5); 2.7308 (14.1); 2.6705 (0.5); 2.6663 (0.4); 2.5238 (1.2); 2.5191 (1.9); 2.5060 (56.4); 2.5016 (77.1); 2.4972 (59.5); 2.4718 (4.2); 5.21.sup.[a] 2.3285 (0.6); 2.2978 (5.5); 2.0730 (0.4) I-199 [00245]
.sup.1H-NMR(400.1 MHz, CDCl3): =7.9985 (4.0); 7.4170 (4.2); 7.4055 (1.0); 7.4000 (0.4); 7.3971 (0.5); 7.3893 (3.8); 7.3834 (3.0); 7.3724 (1.4); 7.3672 (4.0); 7.3620 (2.0); 7.2590 (3.3); 7.0668 (1.8); 7.0539 (1.0); 7.0333 (0.9); 6.9313 (0.4); 6.9236 (3.8); 6.9184 (1.2); 6.9067 (1.2); 6.9015 (3.5); 6.8937 (0.4); 6.8579 (0.4); 6.8421 (1.5); 6.8370 (0.7); 6.8254 (0.6); 6.8200 (1.0); 4.1764 (0.8); 4.1612 (0.8); 4.1394 (1.8); 4.1242 (1.7); 4.1023 (0.9); 4.0872 (0.9); 3.8215 (16.0); 3.7967 (4.1); 2.4936 (5.2); 2.4887 (2.9); 2.3229 (7.2); 1.5699 (1.2); 0.0002 (4.3) 4.49.sup.[a] I-200 [00246]
.sup.1H-NMR(600.1 MHz, d.sub.6-DMSO): = 9.3733 (0.8); 9.3628 (1.6); 9.3524 (0.8); 8.5749 (0.1); 8.3596 (1.3); 8.3462 (1.4); 8.3205 (2.4); 8.2336 (7.0); 8.1251 (1.2); 8.1121 (1.4); 7.9545 (1.8); 7.9141 (1.1); 7.9010 (2.0); 7.8879 (1.0); 7.6362 (1.8); 7.6323 (0.8); 7.6254 (1.3); 7.6213 (7.3); 7.6114 (6.8); 7.6074 (1.4); 7.6005 (0.7); 7.5966 (1.7); 5.9620 (4.0); 4.1385 (0.6); 4.1283 (0.6); 4.1146 (1.3); 4.1032 (1.2); 4.0899 (0.7); 4.0793 (0.6); 3.3256 (59.4); 2.8921 (16.0); 2.7331 (12.4); 2.7323 (12.2); 2.6186 (0.2); 2.6155 (0.3); 2.6125 (0.2); 2.5668 (0.3); 2.5265 (18.4); 2.5216 (1.3); 2.5184 (0.8); 2.5096 (10.9); 2.5066 (24.7); 2.5035 (35.1); 2.5004 (25.3); 2.4974 (11.7); 2.3904 (0.2); 2.3873 (0.2); 2.3843 (0.2); 2.2985 (0.3); 1.2367 (0.1); 0.0054 (0.4); 0.0001 (13.8); 0.0057 (0.4) 3.30.sup.[a] I-201 [00247]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.5488 (0.6); 9.5327 (1.3); 9.5165 (0.6); 7.9535 (0.4); 7.8811 (3.2); 7.8760 (3.4); 7.7618 (3.1); 7.7410 (3.9); 7.5837 (2.2); 7.5785 (2.1); 7.5629 (1.8); 7.5577 (1.8); 7.3714 (2.0); 7.3515 (2.3); 7.1419 (2.3); 7.1183 (1.3); 7.0980 (1.1); 4.0757 (0.6); 4.0596 (0.6); 4.0366 (1.3); 4.0202 (1.3); 3.9972 (0.7); 3.9809 (0.6); 3.3308 (40.6); 2.8917 (2.8); 2.7888 (16.0); 2.7333 (2.3); 2.5262 (0.4); 2.5214 (0.6); 2.5128 (8.7); 2.5083 (18.2); 2.5038 (24.3); 2.4992 (17.4); 2.4948 (8.2); 2.4692 (6.0); 2.3306 (0.3); 2.2960 (8.6) 5.36.sup.[a] I-202 [00248]
.sup.1H-NMR(600.1 MHz, d.sub.6-DMSO): = 9.4319 (0.6); 9.4215 (1.4); 9.4110 (0.7); 8.3599 (1.1); 8.3464 (1.2); 8.3204 (2.1); 8.2150 (5.9); 8.1282 (1.0); 8.1270 (1.0); 8.1152 (1.1); 8.1140 (1.2); 7.9545 (1.8); 7.9166 (1.0); 7.9035 (1.7); 7.8904 (0.8); 7.4891 (2.0); 7.4750 (2.7); 7.4632 (1.7); 7.4606 (1.9); 7.4015 (1.1); 7.3983 (1.0); 7.3875 (0.8); 7.3843 (0.8); 5.9662 (3.5); 4.1372 (0.5); 4.1268 (0.5); 4.1124 (1.2); 4.1018 (1.2); 4.0873 (0.6); 4.0768 (0.5); 3.3252 (46.3); 2.8918 (16.0); 2.7332 (12.5); 2.7322 (12.7); 2.6186 (0.1); 2.6154 (0.3); 2.6124 (0.2); 2.5743 (0.2); 2.5275 (15.6); 2.5214 (1.1); 2.5183 (0.7); 2.5095 (9.8); 2.5065 (22.4); 2.5034 (33.4); 2.5003 (27.2); 2.4973 (15.0); 2.3904 (0.2); 2.3873 (0.2); 2.3842 (0.2); 2.2997 (0.3); 1.2359 (0.1); 0.0054 (0.4); 0.0001 (13.5); 0.0057 (0.5) 3.63.sup.[a] I-203 [00249]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.5484 (0.7); 9.5324 (1.5); 9.5166 (0.8); 7.9535 (0.6); 7.8457 (1.7); 7.8243 (6.5); 7.8097 (6.4); 7.7884 (1.9); 7.3741 (2.2); 7.3543 (2.6); 7.1436 (3.1); 7.1180 (1.7); 7.0979 (1.5); 4.0827 (0.8); 4.0667 (0.8); 4.0435 (1.7); 4.0274 (1.7); 4.0043 (0.9); 3.9883 (0.8); 3.3286 (34.6); 2.8915 (3.3); 2.7843 (16.0); 2.7329 (3.0); 2.5030 (46.5); 2.4717 (7.9); 2.3560 (0.4); 2.3296 (0.6); 2.3252 (0.6); 2.2932 (11.1); 2.2697 (0.6); 2.1300 (0.6) 5.04.sup.[a] I-204 [00250]
.sup.1H-NMR(600.1 MHz, d.sub.6-DMSO): = 9.3950 (0.6); 9.3846 (1.2); 9.3741 (0.6); 8.5444 (0.1); 8.3533 (0.9); 8.3399 (1.0); 8.3139 (1.7); 8.2104 (5.0); 8.1245 (0.9); 8.1115 (1.0); 7.9543 (1.8); 7.9137 (0.8); 7.9005 (1.5); 7.8874 (0.7); 7.8367 (1.8); 7.8333 (1.8); 7.6615 (1.8); 7.6473 (2.7); 7.5971 (1.4); 7.5936 (1.4); 7.5830 (1.0); 7.5795 (1.0); 5.9575 (3.0); 4.2753 (0.4); 4.2648 (0.4); 4.2519 (0.8); 4.2501 (0.8); 4.2415 (0.8); 4.2395 (0.8); 4.2273 (0.4); 4.2158 (0.4); 3.3247 (45.4); 3.3106 (0.1); 2.8920 (16.0); 2.7330 (12.5); 2.7322 (11.9); 2.6185 (0.1); 2.6153 (0.2); 2.6122 (0.1); 2.5438 (0.3); 2.5244 (0.4); 2.5213 (0.5); 2.5182 (0.4); 2.5094 (9.5); 2.5064 (21.5); 2.5033 (30.8); 2.5001 (25.2); 2.4987 (20.6); 2.3901 (0.2); 2.3872 (0.2); 2.3841 (0.1); 2.2963 (0.4); 1.2409 (0.2); 1.2360 (0.2); 0.8538 (0.1); 0.0054 (0.3); 0.0001 (11.3);0.0057 (0.4) 3.62.sup.[a] I-205 [00251]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.5409 (0.6); 9.5253 (1.3); 9.5095 (0.6); 7.9521 (1.1); 7.9358 (2.4); 7.9018 (1.3); 7.8826 (1.6); 7.8709 (1.2); 7.8509 (1.6); 7.7419 (1.3); 7.7224 (1.9); 7.7027 (0.9); 7.3755 (2.0); 7.3556 (2.3); 7.1446 (2.4); 7.1184 (1.4); 7.0979 (1.3); 4.0831 (0.6); 4.0674 (0.6); 4.0442 (1.4); 4.0277 (1.3); 4.0045 (0.7); 3.9887 (0.7); 3.3356 (337.7); 3.3020 (0.7); 2.8912 (7.6); 2.7795 (16.0); 2.7489 (0.4); 2.7322 (6.4); 2.7314 (6.4); 2.6763 (0.5); 2.6717 (0.7); 2.6672 (0.6); 2.5419 (1.2); 2.5251 (2.0); 2.5205 (2.9); 2.5116 (39.8); 2.5072 (84.2); 2.5027 (113.8); 2.4983 (83.8); 2.4723 (6.4); 2.4377 (0.3); 2.3938 (0.4); 2.3339 (0.6); 2.3296 (0.9); 2.3253 (0.7); 2.2936 (9.2); 2.2536 (0.4); 1.2300 (0.3) 5.01.sup.[a] I-206 [00252]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.2636 (0.7); 9.2485 (1.5); 9.2335 (0.9); 7.9967 (5.3); 7.9814 (0.4); 7.4594 (0.4); 7.4467 (0.9); 7.4285 (16.0); 7.3904 (5.9); 7.3725 (2.4); 7.3525 (2.5); 7.1144 (2.6); 7.0736 (1.5); 7.0544 (1.4); 4.0709 (0.7); 4.0553 (0.8); 4.0335 (1.7); 4.0181 (1.7); 3.9962 (1.0); 3.9805 (0.8); 3.3583 (1.7); 3.3346 (27.1); 2.8961 (0.5); 2.7375 (0.5); 2.5121 (22.7); 2.5079 (30.5); 2.5039 (25.3); 2.4416 (7.0); 2.2597 (9.4) 4.46.sup.[a] I-207 [00253]
.sup.1H-NMR(600.1 MHz, d.sub.6-DMSO): = 9.4296 (0.5); 9.4193 (1.0); 9.4088 (0.5); 8.3587 (0.8); 8.3451 (0.9); 8.3203 (1.6); 8.2172 (4.3); 8.1267 (0.8); 8.1135 (0.9); 7.9538 (1.8); 7.9166 (0.7); 7.9034 (1.3); 7.8904 (0.6); 7.6002 (1.4); 7.5375 (0.7); 7.5348 (0.6); 7.5237 (0.8); 7.5209 (0.8); 7.4113 (1.9); 7.3972 (1.6); 5.9648 (2.5); 4.1316 (0.4); 4.1210 (0.4); 4.1066 (0.9); 4.0960 (0.8); 4.0817 (0.4); 4.0711 (0.4); 3.3247 (27.9); 2.8914 (16.0); 2.7325 (11.7); 2.7318 (12.4); 2.6179 (0.1); 2.6149 (0.3); 2.6118 (0.1); 2.5713 (0.2); 2.5244 (11.6); 2.5178 (0.7); 2.5089 (10.5); 2.5059 (23.4); 2.5028 (32.9); 2.4998 (23.7); 2.4967 (12.1); 2.4924 (4.6); 2.3897 (0.2); 2.3867 (0.2); 2.3837 (0.2); 2.2990 (0.2); 0.0054 (0.3); 0.0001 (11.4); 0.0057 (0.4) 3.72.sup.[a] I-208 [00254]
.sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): = 9.5315 (0.6); 9.5159 (1.3); 9.4996 (0.6); 7.9521 (1.1); 7.6271 (3.4); 7.6149 (4.5); 7.6060 (2.4); 7.5183 (0.9); 7.5097 (1.1); 7.5012 (1.1); 7.3714 (2.1); 7.3515 (2.4); 7.1427 (2.6); 7.1156 (1.5); 7.0950 (1.4); 7.0575 (0.3); 6.5283 (0.6); 4.0777 (0.7); 4.0612 (0.7); 4.0388 (1.4); 4.0222 (1.4); 3.9990 (0.8); 3.9831 (0.7); 3.3238 (187.9); 2.8907 (7.8); 2.7817 (16.0); 2.7654 (0.4); 2.7473 (0.5); 2.7313 (6.6); 2.6751 (1.1); 2.6706 (1.6); 2.6663 (1.2); 2.5410 (1.3); 2.5240 (4.3); 2.5191 (6.6); 2.5103 (94.0); 2.5061 (195.1); 2.5017 (261.8); 2.4972 (197.3); 2.4689 (7.3); 2.3942 (0.6); 2.3603 (0.4); 2.3329 (1.4); 2.3283 (1.9); 2.3241 (1.6); 2.2919 (9.9); 1.2586 (0.4); 1.2355 (0.8); 0.0000 (0.5) 5.14.sup.[a] I-209 [00255]
.sup.1H-NMR(600.1 MHz, d.sub.6-DMSO): = 9.0088 (0.5); 8.9993 (0.9); 8.9897 (0.5); 8.3199 (0.8); 8.3060 (1.0); 8.2966 (1.6); 8.2483 (4.5); 8.1468 (0.7); 8.1456 (0.8); 8.1337 (0.8); 8.1325 (0.9); 7.9546 (0.8); 7.9231 (0.7); 7.9100 (1.3); 7.8969 (0.6); 7.4640 (1.1); 7.4615 (0.9); 7.4515 (1.5); 7.4486 (1.4); 7.4069 (0.8); 7.4036 (1.0); 7.3945 (1.0); 7.3915 (1.2); 7.3310 (0.5); 7.3284 (0.6); 7.3187 (1.4); 7.3161 (1.4); 7.3068 (1.2); 7.3041 (1.7); 7.3008 (1.2); 7.2917 (1.1); 7.2885 (1.2); 7.2793 (0.4); 7.2762 (0.4); 3.5937 (0.7); 3.5821 (1.6); 3.5722 (1.6); 3.5606 (0.7); 3.48.sup.[a] 3.3241 (35.1); 3.0147 (1.3); 3.0030 (2.5); 2.9912 (1.2); 2.8919 (7.3); 2.8838 (0.1); 2.7707 (16.0); 2.7332 (5.6); 2.7323 (5.8); 2.6335 (12.2); 2.6219 (0.1); 2.6185 (0.2); 2.6155 (0.2); 2.6125 (0.1); 2.5245 (0.4); 2.5215 (0.4); 2.5183 (0.4); 2.5096 (7.5); 2.5065 (17.1); 2.5035 (24.5); 2.5004 (17.7); 2.4973 (8.2); 2.3904 (0.1); 2.3874 (0.2); 2.3842 (0.1); 0.0054 (0.3); 0.0001 (10.1); 0.0057 (0.3)
[1166] The following compounds of formula (I-A) may be prepared according to the processes disclosed herein: [1167] 6-chloro-3-[(3-cyclopropyl-2-fluorophenyl)sulfanyl]-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carboxamide [1168] 6-chloro-N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-3-[(3-cyclopropyl-2-fluorophenyl)sulfanyl]-5-methylpyridazine-4-carboxamide [1169] N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-5-[(3-cyclopropyl-2-fluorophenyl)sulfanyl]-2-methylisonicotinamide [1170] 5-[(3-cyclopropyl-2-fluorophenyl)sulfanyl]-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]-2-methylisonicotinamide [1171] 5-[(3-cyclopropyl-2-fluorophenyl)sulfanyl]-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]-2-methylpyrimidine-4-carboxamide [1172] N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-5-[(3-cyclopropyl-2-fluorophenyl)sulfanyl]-2-methylpyrimidine-4-carboxamide [1173] N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-3-[(3-cyclopropyl-2-fluorophenyl)sulfanyl]quinoline-4-carboxamide [1174] 3-[(3-cyclopropyl-2-fluorophenyl)sulfanyl]-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]quinoline-4-carboxamide [1175] 3-[(3-cyclopropyl-2-fluorophenyl)sulfanyl]-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]cinnoline-4-carboxamide [1176] N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-3-[(3-cyclopropyl-2-fluorophenyl)sulfanyl]cinnoline-4-carboxamide [1177] N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-3-[(3-cyclopropyl-2-fluorophenyl)sulfanyl]-5,6,7,8-tetrahydrocinnoline-4-carboxamide [1178] 3-[(3-cyclopropyl-2-fluorophenyl)sulfanyl]-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]-5,6,7,8-tetrahydrocinnoline-4-carboxamide [1179] 6-chloro-3-[(3-cyclopropyl-2-fluorophenyl)sulfinyl]-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carboxamide [1180] 6-chloro-N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-3-[(3-cyclopropyl-2-fluorophenyl)sulfinyl]-5-methylpyridazine-4-carboxamide [1181] N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-5-[(3-cyclopropyl-2-fluorophenyl)sulfinyl]-2-methylisonicotinamide [1182] 5-[(3-cyclopropyl-2-fluorophenyl)sulfinyl]-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]-2-methylisonicotinamide [1183] 5-[(3-cyclopropyl-2-fluorophenyl)sulfinyl]-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]-2-methylpyrimidine-4-carboxamide [1184] N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-5-[(3-cyclopropyl-2-fluorophenyl)sulfinyl]-2-methylpyrimidine-4-carboxamide [1185] N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-3-[(3-cyclopropyl-2-fluorophenyl)sulfinyl]quinoline-4-carboxamide [1186] 3-[(3-cyclopropyl-2-fluorophenyl)sulfinyl]-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]quinoline-4-carboxamide [1187] 3-[(3-cyclopropyl-2-fluorophenyl)sulfinyl]-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]cinnoline-4-carboxamide [1188] N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-3-[(3-cyclopropyl-2-fluorophenyl)sulfinyl]cinnoline-4-carboxamide [1189] N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-3-[(3-cyclopropyl-2-fluorophenyl)sulfinyl]-5,6,7,8-tetrahydrocinnoline-4-carboxamide [1190] 3-[(3-cyclopropyl-2-fluorophenyl)sulfinyl]-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]-5,6,7,8-tetrahydrocinnoline-4-carboxamide [1191] N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-3-[(3-cyclopropyl-2-fluorophenyl)sulfonyl]-5,6,7,8-tetrahydrocinnoline-4-carboxamide [1192] 3-[(3-cyclopropyl-2-fluorophenyl)sulfonyl]-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]-5,6,7,8-tetrahydrocinnoline-4-carboxamide [1193] 6-chloro-3-[(3-cyclopropyl-2-fluorophenyl)sulfonyl]-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carboxamide [1194] 6-chloro-N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-3-[(3-cyclopropyl-2-fluorophenyl)sulfonyl]-5-methylpyridazine-4-carboxamide [1195] N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-5-[(3-cyclopropyl-2-fluorophenyl)sulfonyl]-2-methylisonicotinamide [1196] 5-[(3-cyclopropyl-2-fluorophenyl)sulfonyl]-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]-2-methylisonicotinamide [1197] 5-[(3-cyclopropyl-2-fluorophenyl)sulfonyl]-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]-2-methylpyrimidine-4-carboxamide [1198] N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-5-[(3-cyclopropyl-2-fluorophenyl)sulfonyl]-2-methylpyrimidine-4-carboxamide [1199] N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-3-[(3-cyclopropyl-2-fluorophenyl)sulfonyl]quino-line-4-carboxamide [1200] 3-[(3-cyclopropyl-2-fluorophenyl)sulfonyl]-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]quinoline-4-carboxamide [1201] 3-[(3-cyclopropyl-2-fluorophenyl)sulfonyl]-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]cinnoline-4-carboxamide [1202] N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-3-[(3-cyclopropyl-2-fluorophenyl)sulfonyl]cinnoline-4-carboxamide [1203] 6-[(3-cyclopropyl-2-fluorophenyl)sulfanyl]-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]-3-methyl-1,2,4-triazine-5-carboxamide [1204] N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-6-[(3-cyclopropyl-2-fluorophenyl)sulfanyl]-3-methyl-1,2,4-triazine-5-carboxamide [1205] N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-6-[(3-cyclopropyl-2-fluorophenyl)sulfinyl]-3-methyl-1,2,4-triazine-5-carboxamide [1206] 6-[(3-cyclopropyl-2-fluorophenyl)sulfinyl]-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]-3-methyl-1,2,4-triazine-5-carboxamide [1207] 6-[(3-cyclopropyl-2-fluorophenyl)sulfonyl]-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]-3-methyl-1,2,4-triazine-5-carboxamide [1208] N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-6-[(3-cyclopropyl-2-fluorophenyl)sulfonyl]-3-methyl-1,2,4-triazine-5-carboxamide [1209] 6-chloro-3-[S-(3-cyclopropyl-2-fluorophenyl)sulfonimidoyl]-N-[2-(2,4-dimethylphenyl)-2,2-difluoro-ethyl]-5-methylpyridazine-4-carboxamide [1210] 6-chloro-N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-3-[S-(3-cyclopropyl-2-fluoro-phenyl)sulfonimidoyl]-5-methylpyridazine-4-carboxamide [1211] N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-5-[S-(3-cyclopropyl-2-fluorophenyl)sulfonimidoyl]-2-methylisonicotinamide [1212] 5-[S-(3-cyclopropyl-2-fluorophenyl)sulfonimidoyl]-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]-2-methylisonicotinamide [1213] 3-[S-(3-cyclopropyl-2-fluorophenyl)sulfonimidoyl]-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]quinoline-4-carboxamide [1214] N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-3-[S-(3-cyclopropyl-2-fluorophenyl)sulfonimidoyl]quinoline-4-carboxamide [1215] N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-5-[S-(3-cyclopropyl-2-fluorophenyl)sulfonimidoyl]-2-methylpyrimidine-4-carboxamide [1216] 5-[S-(3-cyclopropyl-2-fluorophenyl)sulfonimidoyl]-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]-2-methylpyrimidine-4-carboxamide [1217] N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-3-[S-(3-cyclopropyl-2-fluorophenyl)sulfonimidoyl]-5,6,7,8-tetrahydrocinnoline-4-carboxamide [1218] 3-[S-(3-cyclopropyl-2-fluorophenyl)sulfonimidoyl]-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]-5,6,7,8-tetrahydrocinnoline-4-carboxamide [1219] N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-3-[S-(3-cyclopropyl-2-fluorophenyl)sulfonimidoyl]cinnoline-4-carboxamide [1220] 3-[S-(3-cyclopropyl-2-fluorophenyl)sulfonimidoyl]-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]cinnoline-4-carboxamide [1221] 6-[S-(3-cyclopropyl-2-fluorophenyl)sulfonimidoyl]-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]-3-methyl-1,2,4-triazine-5-carboxamide [1222] N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-6-[S-(3-cyclopropyl-2-fluorophenyl)sulfonimidoyl]-3-methyl-1,2,4-triazine-5-carboxamide [1223] N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-6-[S-(3-cyclopropyl-2-fluorophenyl)-N-methylsulfonimidoyl]-3-methyl-1,2,4-triazine-5-carboxamide [1224] 6-[S-(3-cyclopropyl-2-fluorophenyl)-N-methylsulfonimidoyl]-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]-3-methyl-1,2,4-triazine-5-carboxamide [1225] 3-[S-(3-cyclopropyl-2-fluorophenyl)-N-methylsulfonimidoyl]-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]cinnoline-4-carboxamide [1226] N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-3-[S-(3-cyclopropyl-2-fluorophenyl)-N-methylsulfonimidoyl]cinnoline-4-carboxamide [1227] 3-[S-(3-cyclopropyl-2-fluorophenyl)-N-methylsulfonimidoyl]-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]-5,6,7,8-tetrahydrocinnoline-4-carboxamide [1228] N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-3-[S-(3-cyclopropyl-2-fluorophenyl)-N-methylsulfonimidoyl]-5,6,7,8-tetrahydrocinnoline-4-carboxamide [1229] 5-[S-(3-cyclopropyl-2-fluorophenyl)-N-methylsulfonimidoyl]-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]-2-methylpyrimidine-4-carboxamide [1230] N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-5-[S-(3-cyclopropyl-2-fluorophenyl)-N-methylsulfonimidoyl]-2-methylpyrimidine-4-carboxamide [1231] N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-3-[S-(3-cyclopropyl-2-fluorophenyl)-N-methylsulfonimidoyl]quinoline-4-carboxamide [1232] 3-[S-(3-cyclopropyl-2-fluorophenyl)-N-methylsulfonimidoyl]-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]quinoline-4-carboxamide [1233] 5-[S-(3-cyclopropyl-2-fluorophenyl)-N-methylsulfonimidoyl]-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]-2-methylisonicotinamide [1234] N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-5-[S-(3-cyclopropyl-2-fluorophenyl)-N-methylsulfonimidoyl]-2-methylisonicotinamide [1235] 6-chloro-N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-3-[S-(3-cyclopropyl-2-fluorophenyl)-N-methylsulfonimidoyl]-5-methylpyridazine-4-carboxamide [1236] 6-chloro-3-[S-(3-cyclopropyl-2-fluorophenyl)-N-methylsulfonimidoyl]-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carboxamide
[1237] Table 3: Compounds of formula (1)
##STR00256##
TABLE-US-00002 TABLE 3 Compounds according to formula (1), their .sup.1H-NMR data and LogP values Ex N.sup.o Structure .sup.1H-NMR Peak List LogP 1-01 [00257]
.sup.1H-NMR (400.1 MHz, CDC13): = 7.3676 (1.1); 7.3478 (1.9); 7.3278 (1.5); 7.2626 (4.0); 7.1882 (1.0); 7.1853 (1.4); 7.1827 (1.1); 7.1693 (0.8); 7.1659 (1.1); 7.1637 (0.9); 7.1380 (1.4); 7.1321 (1.8); 7.1280 (1.3); 7.0012 (1.0); 6.9993 (1.0); 6.9949 (0.9); 6.9931 (0.9); 6.9804 (0.9); 6.9784 (0.9); 6.9741 (0.8); 6.9722 (0.8); 4.5836 (1.2); 4.5658 (3.8); 4.5479 (3.9); 4.5301 (1.3); 3.8048 (15.9); 2.8699 (16.0); 1.5777 (1.2); 1.5077 (4.0); 1.4899 (8.2); 1.4720 (4.0); 0.0703 (0.3); 0.0002 (4.6) 3.01.sup.[a] 1-02 [00258]
.sup.1H-NMR (400.1 MHz, CDC13): = 7.8091 (6.2); 7.7630 (3.4); 7.7435 (3.9); 7.6060 (3.0); 7.5865 (4.2); 7.4995 (3.4); 7.4799 (5.2); 7.4604 (2.2); 7.2628 (29.8); 5.3003 (1.6); 4.4965 (3.5); 4.4828 (5.4); 4.4786 (11.4); 4.4650 (16.0); 4.4608 (12.5); 4.4471 (16.0); 4.4431 (5.5); 4.4293 (5.4); 3.6200 (1.1); 3.1790 (3.5); 3.1628 (7.4); 3.1467 (4.5); 3.1316 (4.8); 3.1154 (10.0); 3.0993 (6.1); 2.8261 (5.3); 2.8095 (12.4); 2.7923 (10.9); 2.7753 (4.1); 1.9698 (1.0); 1.9616 (1.0); 1.9539 (2.5); 1.9475 (2.7); 1.9407 (4.7); 1.9322 (4.8); 1.9252 (6.6); 1.9204 (5.7); 1.9099 (4.7); 1.9053 (5.5); 1.8943 (2.2); 1.8888 (2.4); 1.8770 (1.0); 1.8685 (1.7); 1.8622 (2.2); 1.8527 (5.4); 1.8404 (6.8); 1.8378 (6.7); 1.8254 (6.6); 1.8128 (3.8); 1.7973 (1.6); 1.5959 (0.5); 1.5836 (47.2); 1.5651 (0.7); 1.4422 (16.3); 1.4380 (12.8); 1.4243 (33.4); 1.4201 (25.9); 1.4065 (16.7); 1.4023 (13.0); 1.3717 (0.8); 1.3336 (0.5); 1.3121 (0.4); 1.2858 (0.8); 1.2629 (0.9); 1.2544 (1.3); 0.8806 (0.4); 0.0700 (7.9); 0.0608 (0.4); 0.0080 (1.0); 0.0002 (35.2); -0.0084 (1.8) 4.19.sup.[a] 1-03 [00259]
.sup.1H-NMR (400.1 MHz, d.sub.6-DMSO): = 14.6847 (0.4); 14.6778 (0.4); 14.6141 (0.4); 14.6026 (0.4); 14.5151 (0.4); 7.8501 (11.9); 7.7940 (6.1); 7.7838 (7.0); 7.7750 (8.8); 7.7667 (8.6); 7.7639 (8.8); 7.6792 (6.8); 7.6597 (9.1); 7.6401 (3.9); 5.7576 (4.2); 4.4657 (1.2); 4.4478 (3.7); 4.4301 (3.8); 4.4124 (1.4); 4.3947 (0.6); 4.3768 (0.6); 3.6480 (0.3); 3.6280 (0.4); 3.6147 (0.7); 3.5992 (0.5); 3.5681 (6.2); 3.5524 (0.6); 3.4985 (1.0); 3.4831 (1.1); 3.4492 (1.6); 3.4321 (2.0); 3.3375 (3.7); 3.2516 (1.9); 3.2362 (1.7); 3.2204 (1.4); 3.1688 (3.5); 3.1529 (0.7); 3.1035 (0.6); 3.0724 (1.7); 3.0581 (5.6); 3.0436 (9.0); 3.0277 (5.6); 3.0142 (7.7); 2.9983 (15.6); 2.9823 (9.4); 2.8476 (0.4); 2.8033 (8.0); 2.7873 (16.0); 2.7711 (11.0); 2.7661 (11.7); 2.7503 (5.8); 2.7405 (2.5); 2.6716 (0.6); 2.5112 (18.6); 2.5068 (39.7); 2.5023 (55.4); 2.4979 (42.2); 2.4935 (21.9); 2.3295 (0.4); 1.9092 (3.5); 1.8818 (1.3); 1.8668 (5.0); 1.8527 (9.2); 1.8435 (10.4); 1.8388 (12.0); 1.8284 (9.0); 1.8241 (9.4); 1.8078 (4.2); 1.7832 (5.4); 1.7735 (8.6); 1.7676 (11.0); 1.7610 (10.8); 1.7533 (11.2); 1.7474 (9.6); 1.3509 (5.0); 1.3331 (8.3); 1.3153 (4.0); 1.3103 (1.8); 1.2987 (1.2); 1.2925 (1.0); 1.2583 (1.6); 1.2494 (1.5); 1.2345 (2.5); 1.0733 (0.5); 1.0558 (1.0); 1.0384 (0.5); 0.8535 (0.5); 0.8346 (0.4); 0.1461 (0.3); 0.0080 (2.6);0.0002 (77.1); 0.0082 (4.2); 0.1490 (0.4) 1.67.sup.[a] 1-04 [00260]
.sup.1H-NMR (300.1 MHz, d.sub.6-DMSO): = 8.2078 (6.0); 7.9616 (3.3); 7.9284 (1.8); 7.9009 (3.4); 7.8716 (2.1); 7.7633 (1.6); 7.7375 (2.1); 7.7114 (0.9); 3.9643 (16.0); 3.3418 (4.9); 2.5078 (3.2) 3.84.sup.[a] 1-05 [00261]
.sup.1H-NMR (400.1 MHz, d.sub.6-DMSO): = 7.9964 (2.9); 7.9310 (1.6); 7.9116 (1.9); 7.8854 (1.4); 7.8659 (1.8); 7.7806 (5.4); 7.7571 (1.4); 7.7375 (2.1); 7.7180 (0.9); 3.8628 (17.0); 3.3312 (4.8); 3.3088 (1.0); 2.7623 (16.0); 2.5060 (7.6) 3.33.sup.[a]
[1238] Table 4: Compounds of formula (1 6)
##STR00262##
TABLE-US-00003 TABLE 4 Compounds according to formula (1-f), their .sup.1H-NMR data and LogP values Ex N.sup.o Structure .sup.1H-NMR Peak List LogP 1-f01 [00263]
.sup.1H-NMR (300.0 MHz, d.sub.6-DMSO): = 8.3568 (5.2); 8.3205 (1.4); 8.2986 (3.3); 8.1334 (1.1); 8.1073 (1.4); 7.9130 (1.0); 7.8865 (1.6); 7.8597 (0.7); 3.1769 (4.2); 2.8243 (13.4); 2.7528 (16.0); 2.5639 (0.4); 2.5189 (1.9); 2.5130 (2.4); 2.5073 (1.6); 2.3950 (0.5); 1.9174 (2.0); 1.7668 (2.1); 0.0001 (0.9) 1.94.sup.[a] 1-f02 [00264]
.sup.1H-NMR (300.0 MHz, CDC13): = 8.6726 (3.6); 8.4567 (0.9); 8.4350 (2.1); 7.8919 (0.7); 7.8659 (1.0); 7.7361 (0.7); 7.7340 (0.7); 7.7080 (1.1); 7.6817 (0.5); 7.6798 (0.5); 7.2647 (4.1); 4.0196 (16.0); 3.0453 (12.2); 2.0078 (2.7); 0.0001 (3.5) 2.24.sup.[a] 1-f03 [00265]
.sup.1H-NMR (300.0 MHz, d.sub.6-DMSO): = 8.5874 (6.5); 8.3853 (1.5); 8.3581 (1.8); 8.3367 (2.8); 8.1299 (1.4); 8.1037 (1.7); 7.9189 (1.3); 7.8927 (2.1); 7.8666 (0.9); 7.1851 (0.3); 3.1735 (2.0); 2.8954 (16.0); 2.8155 (0.9); 2.5141 (3.4); 2.5084 (4.5); 2.5028 (3.2); 0.0001 (2.3) 1.48.sup.[a]
B. BIOLOGICAL EXAMPLES
B-1. In Vivo Preventive Test on Alternaria brassicae (Leaf Spot on Radish or Cabbage) [1239] Solvent: 5% by volume of Dimethyl sulfoxide [1240] 10% by volume of Acetone [1241] Emulsifier: 1 l of Tween 80 per mg of active ingredient
[1242] The active ingredients were made soluble and homogenized in a mixture of Dimethyl sulfoxide/Acetone/Tween80 and then diluted in water to the desired concentration.
[1243] The young plants of radish or cabbage were treated by spraying the active ingredient prepared as described above. Control plants were treated only with an aqueous solution of Acetone/Dimethyl sulfoxide/Tween 80.
[1244] After 24 hours, the plants were contaminated by spraying the leaves with an aqueous suspension of Alternaria brassicae spores. The contaminated radish or cabbage plants were incubated for 3 to 4 days at 20 C. and at 100% relative humidity.
[1245] The test was evaluated 3 to 4 days after the inoculation. 0% means an efficacy which corresponds to that of the control plants while an efficacy of 100% means that no disease was observed.
[1246] In this test the following compounds according to the invention showed efficacy between 70% and 79% at a concentration of 500 ppm of active ingredient: I-018; I-050
[1247] In this test the following compounds according to the invention showed efficacy between 80% and 89% at a concentration of 500 ppm of active ingredient: I-194
[1248] In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 500 ppm of active ingredient: I-080
B-2. In Vivo Preventive Test on Botrytis cinerea (Grey Mould) [1249] Solvent: 5% by volume of Dimethyl sulfoxide [1250] 10% by volume of Acetone [1251] Emulsifier: 1 l of Tween 80 per mg of active ingredient
[1252] The active ingredients were made soluble and homogenized in a mixture of Dimethyl sulfoxide/Acetone/Tween80 and then diluted in water to the desired concentration.
[1253] The young plants of gherkin or cabbage were treated by spraying the active ingredient prepared as described above. Control plants were treated only with an aqueous solution of Acetone/Dimethyl sulfoxide/Tween80.
[1254] After 24 hours, the plants were contaminated by spraying the leaves with an aqueous suspension of Botrytis cinerea spores. The contaminated gherkin plants were incubated for 4 to 5 days at 17 C. and at 90% relative humidity. The contaminated cabbage plants were incubated for 4 to 5 days at 20 C. and at 100% relative humidity.
[1255] The test was evaluated 4 to 5 days after the inoculation. 0% means an efficacy which corresponds to that of the control plants while an efficacy of 100% means that no disease was observed.
[1256] In this test the following compounds according to the invention showed efficacy between 70% and 79% at a concentration of 500 ppm of active ingredient: I-096
[1257] In this test the following compounds according to the invention showed efficacy between 80% and 89% at a concentration of 500 ppm of active ingredient: I-036
[1258] In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 500 ppm of active ingredient: I-050
B-3. In Vivo Preventive Test on Sphaerotheca fuliginea (Powdery Mildew on Cucurbits) [1259] Solvent: 5% by volume of Dimethyl sulfoxide [1260] 10% by volume of Acetone [1261] Emulsifier: 1 l of Tween 80 per mg of active ingredient
[1262] The active ingredients were made soluble and homogenized in a mixture of Dimethyl sulfoxide/Acetone/Tween80 and then diluted in water to the desired concentration.
[1263] The young plants of gherkin were treated by spraying the active ingredient prepared as described above. Control plants were treated only with an aqueous solution of Acetone/Dimethyl sulfoxide/Tween80.
[1264] After 24 hours, the plants were contaminated by spraying the leaves with an aqueous suspension of Sphaerotheca fuliginea spores. The contaminated gherkin plants were incubated for 8 days at 20 C. and at 70-80% relative humidity.
[1265] The test was evaluated 8 days after the inoculation. 0% means an efficacy which corresponds to that of the control plants while an efficacy of 100% means that no disease was observed.
[1266] In this test the following compounds according to the invention showed efficacy between 80% and 89% at a concentration of 500 ppm of active ingredient: I-117; I-161; I-170
[1267] In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 500 ppm of active ingredient: I-050
B-4. In Vivo Preventive Test on Colletotrichum lindemuthianum (Leaf Spot on Bean) [1268] Solvent: 5% by volume of Dimethyl sulfoxide [1269] 10% by volume of Acetone [1270] Emulsifier: 1 l of Tween 80 per mg of active ingredient
[1271] The active ingredients were made soluble and homogenized in a mixture of Dimethyl sulfoxide/Acetone/Tween80 and then diluted in water to the desired concentration.
[1272] The young plants of bean were treated by spraying the active ingredient prepared as described above. Control plants were treated only with an aqueous solution of Acetone/Dimethyl sulfoxide/Tween80.
[1273] After 24 hours, the plants were contaminated by spraying the leaves with an aqueous suspension of Colletotrichum lindemuthianum spores. The contaminated bean plants were incubated for 24 hours at 20 C. and at 100% relative humidity and then for 6 days at 20 C. and at 90% relative humidity.
[1274] The test was evaluated 7 days after the inoculation. 0% means an efficacy which corresponds to that of the control plants while an efficacy of 100% means that no disease was observed.
[1275] In this test the following compounds according to the invention showed efficacy between 80% and 89% at a concentration of 500 ppm of active ingredient: I-041; I-170
[1276] In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 500 ppm of active ingredient: I-050
B-5. Alternaria alternata In Vitro Cell Test [1277] Solvent: DMSO [1278] Culture medium: 14.6 g anhydrous D-glucose (VWR), 7.1 g Mycological Peptone (Oxoid), 1.4 g granulated Yeast Extract (Merck), QSP 1 liter [1279] Inoculum: spores suspension
[1280] Fungicides were solubilized in DMSO and the solution used to prepare the required range of concentrations. The final concentration of DMSO used in the assay was 1%.
[1281] A spore suspension of A. alternata was prepared and diluted to the desired spore density.
[1282] Fungicides were evaluated for their ability to inhibit spore germination and mycelium growth in liquid culture assay. The compounds were added in the desired concentration to the culture medium with spores. After 5 days incubation, fungi-toxicity of compounds was determined by spectrometric measurement of mycelium growth. Inhibition of fungal growth was determined by comparing the absorbance values in wells containing the fungicides with the absorbance in control wells without fungicides.
[1283] In this test the following compounds according to the invention showed efficacy between 70% and 79% at a concentration of 50 Mol/l of active ingredient: I-104; I-105; I-117; I-161; I-176; I-200
[1284] In this test the following compounds according to the invention showed efficacy between 80% and 89% at a concentration of 50 Mol/l of active ingredient: I-128
[1285] In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 20 ppm of active ingredient: I-021
B-6. Colletotrichum lindemuthianum In Vitro Cell Test [1286] Solvent: DMSO [1287] Culture medium: 14.6 g anhydrous D-glucose (VWR), 7.1 g Mycological Peptone (Oxoid), 1.4 g granulated Yeast Extract (Merck), QSP 1 liter [1288] Inoculum: spores suspension
[1289] Fungicides were solubilized in DMSO and the solution used to prepare the required range of concentrations. The final concentration of DMSO used in the assay was 1%.
[1290] A spore suspension of C. lindemuthianum was prepared and diluted to the desired spore density.
[1291] Fungicides were evaluated for their ability to inhibit spores germination and mycelium growth in liquid culture assay. The compounds were added in the desired concentration to the culture medium with spores.
[1292] After 6 days incubation, fungi-toxicity of compounds was determined by spectrometric measurement of mycelium growth. Inhibition of fungal growth was determined by comparing the absorbance values in wells containing the fungicides with the absorbance in control wells without fungicides.
[1293] In this test the following compounds according to the invention showed efficacy between 70% and 79% at a concentration of 50 Mol/l of active ingredient: I-194
[1294] In this test the following compounds according to the invention showed efficacy between 80% and 89% at a concentration of 50 Mol/l of active ingredient: I-179
[1295] In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 50 Mol/l of active ingredient: I-096; I-114; I-117; I-134; I-161; I-170
[1296] In this test the following compounds according to the invention showed efficacy between 70% and 79% at a concentration of 20 ppm of active ingredient: I-051
[1297] In this test the following compounds according to the invention showed efficacy between 80% and 89% at a concentration of 20 ppm of active ingredient: I-082
[1298] In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 20 ppm of active ingredient: I-018; I-019; I-036; I-050
B-7. Botrytis cinerea In Vitro Cell Test [1299] Solvent: DMSO [1300] Culture medium: 1 g KH.sub.2PO.sub.4 (VWR), 1 g K.sub.2HPO.sub.4 (VWR), 0.5 g Urea (VWR), 3 g KNO.sub.3 (Prolabo), 10 g saccharose (VWR), 0.5 g MgSO.sub.4, 7H.sub.2O (Sigma), 0.07 g CaCl.sub.2, 2H.sub.2O (Prolabo), 0.2 mg MnSO.sub.4, H.sub.2O (Sigma), 0.6 mg CuSO.sub.4, 5H.sub.2O (Sigma), 7.9 mg ZnSO.sub.4, 7H.sub.2O (Sigma), 0.1 mg H.sub.3BO.sub.3 (Merck), 0.14 mg NaMoO.sub.4, 2H.sub.2O (Sigma), 2 mg thiamine (Sigma), 0.1 mg biotine (VWR), 4 mg FeSO.sub.4, 7H.sub.2O (Sigma), QSP 1 liter [1301] Inoculum: spore suspension
[1302] Fungicides were solubilized in DMSO and the solution used to prepare the required range of concentrations. The final concentration of DMSO used in the assay was 1%.
[1303] A spore suspension of B. cinerea was prepared and diluted to the desired spore density.
[1304] Fungicides were evaluated for their ability to inhibit spore germination and mycelium growth in liquid culture assay. The compounds were added in the desired concentration to the culture medium with spores. After 6 days incubation, fungi-toxicity of compounds was determined by spectrometric measurement of mycelium growth. Inhibition of fungal growth was determined by comparing the absorbance values in wells containing the fungicides with the absorbance in control wells without fungicides.
[1305] In this test the following compounds according to the invention showed efficacy between 70% and 79% at a concentration of 50 Mol/l of active ingredient: I-110
[1306] In this test the following compounds according to the invention showed efficacy between 80% and 89% at a concentration of 50 Mol/l of active ingredient: I-105; I-114; I-200
[1307] In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 50 Mol/l of active ingredient: I-094; I-096; I-104; I-116; I-117; I-125; I-128; I-134; I-158; I-161; I-170; I-173; I-176; I-179; I-191; I-194
[1308] In this test the following compounds according to the invention showed efficacy between 80% and 89% at a concentration of 20 ppm of active ingredient: I-011; I-014; I-051
[1309] In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 20 ppm of active ingredient: I-036; I-050
B-8. Pyricularia oryzae in vitro cell test [1310] Solvent: DMSO [1311] Culture medium: 14.6 g anhydrous D-glucose (VWR), 7.1 g Mycological Peptone (Oxoid), 1.4 g granulated Yeast Extract (Merck), QSP lliter [1312] Inoculum: spore suspension
[1313] Fungicides were solubilized in DMSO and the solution used to prepare the required range of concentrations. The final concentration of DMSO used in the assay was 1%.
[1314] A spore suspension of P. oryzae was prepared and diluted to the desired spore density.
[1315] Fungicides were evaluated for their ability to inhibit spore germination and mycelium growth in liquid culture assay. The compounds were added in the desired concentration to the culture medium with spores. After 5 days incubation, fungi-toxicity of compounds was determined by spectrometric measurement of mycelium growth. Inhibition of fungal growth was determined by comparing the absorbance values in wells containing the fungicides with the absorbance in control wells without fungicides.
[1316] In this test the following compounds according to the invention showed efficacy between 70% and 79% at a concentration of 50 Mol/l of active ingredient: I-094; I-114; I-147; I-160
[1317] In this test the following compounds according to the invention showed efficacy between 80% and 89% at a concentration of 50 Mol/l of active ingredient: I-128; I-134; I-161; I-173; I-194
[1318] In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 50 Mol/l of active ingredient: I-096; I-104; I-117; I-125; I-170
B-9. Pyrenophora teres In Vitro Cell Test [1319] Solvent: DMSO [1320] Culture medium: 14.6 g anhydrous D-glucose (VWR), 7.1 g Mycological Peptone (Oxoid), 1.4 g granulated Yeast Extract (Merck), QSP 1 liter [1321] Inoculum: spore suspension
[1322] Fungicides were solubilized in DMSO and the solution used to prepare the required range of concentrations. The final concentration of DMSO used in the assay was 1%.
[1323] A spore suspension of P. teres was prepared and diluted to the desired spore density.
[1324] Fungicides were evaluated for their ability to inhibit spore germination and mycelium growth in liquid culture assay. The compounds were added in the desired concentration to the culture medium with spores. After 6 days incubation, fungi-toxicity of compounds was determined by spectrometric measurement of mycelium growth. Inhibition of fungal growth was determined by comparing the absorbance values in wells containing the fungicides with the absorbance in control wells without fungicides.
[1325] In this test the following compounds according to the invention showed efficacy between 70% and 79% at a concentration of 50 Mol/l of active ingredient: I-138; I-140; I-192; I-200; I-206
[1326] In this test the following compounds according to the invention showed efficacy between 80% and 89% at a concentration of 50 Mol/l of active ingredient: I-105; I-113; I-114
[1327] In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 50 Mol/l of active ingredient: I-094; I-096; I-104; I-116; I-117; I-125; I-128; I-134; I-158; I-161; I-170; I-173; I-176; I-191; I-194