Abstract
The invention relates to novel compounds of the formula (I)
##STR00001##
in which Ar represents phenyl or a 5- or 6-membered heteroaromatic ring and A, R.sup.1 and R.sup.2 have the meanings given above, and their use for controlling animal pests, especially arthropods and in particular insects, arachnids and nematodes.
Claims
1. Compound of the A compound of formula (I) ##STR00267## wherein Ar is a phenyl or a 5- or 6-membered heteroaromatic ring, in each case unsubstituted or substituted by 1 to 4 R.sup.Ar; wherein each R.sup.Ar is independently halogen, cyano, nitro, SF.sub.5, C(Q.sup.1)R.sup.a, C(O)OR.sup.a, C(Q.sup.1)NR.sup.bR.sup.c, NR.sup.dR.sup.e, OR.sup.a, S(O).sub.nR.sup.a or SO.sub.2NR.sup.bR.sup.c; or C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl or C.sub.3-C.sub.7-cycloalkyl, all of which may in each case be unsubstituted or mono- to tridecasubstituted by halogen and/or optionally by 1 to 3 R.sup.f; or phenyl, a 5- or 6-membered heteroaromatic ring or a 7- to 11-membered heteroaromatic ring system, all in each case unsubstituted or substituted by 1 to 3 R.sup.g; A represents is N or CR.sup.A; wherein R.sup.A is H, halogen, cyano, nitro, SF.sub.5, C(Q.sup.1)R.sup.a, C(O)OR.sup.a, C(Q.sup.1)NR.sup.bR.sup.c, NR.sup.dR.sup.e, OR.sup.a, S(O).sub.nR.sup.a or SO.sub.2NR.sup.bR.sup.c; or C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl or C.sub.3-C.sub.7-cycloalkyl, all of which may in each case be unsubstituted or mono- to tridecasubstituted by halogen and/or optionally by 1 to 3 R.sup.f; or phenyl, a 5- or 6-membered heteroaromatic ring or a 7- to 11-membered heterocyclic aromatic ring system, all in each case unsubstituted or substituted by 1 to 3 R.sup.g; R.sup.1 is NR.sup.11R.sup.12, —N(R.sup.b)NR.sup.dR.sup.e, —N(R.sup.b)OR.sup.a, —N(R.sup.b)—CN, —N(R.sup.11)C(Q.sup.1)R.sup.b, —N(R.sup.11)C(Q.sup.1)NR.sup.bR.sup.c, —N(R.sup.11)C(O)OR.sup.a, —N(R.sup.11)C(O)C(O)R.sup.b, —N(R.sup.11)C(O)C(O)OR.sup.a, —N(R.sup.11)C(O)C(O)NR.sup.bR.sup.c, —N(R.sup.11)SO.sub.2R.sup.a, —N═C(R.sup.b)N(R.sup.b)(R.sup.c), —N═C(R.sup.b)(R.sup.c), —N═S (O)R.sup.aR.sup.a or —N═SR.sup.aR.sup.a; wherein R.sup.11 is H; or C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl or C.sub.3-C.sub.7-cycloalkyl, all of which may in each case be unsubstituted or mono- to pentasubstituted by halogen and/or optionally by 1 to 2 R.sup.b; or phenyl or a 4- to 7-membered saturated, partially saturated or aromatic heterocycle having 1 to 3 heteroatoms, in each case unsubstituted or substituted by 1 to 5 R.sup.g; R.sup.12 is H; or C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl or C.sub.3-C.sub.7-cycloalkyl, all in each case unsubstituted or substituted by 1 to 5 R.sup.g; or R.sup.11 and R.sup.12 together with the nitrogen atom to which they are attached represent form an optionally substituted saturated, partially saturated or aromatic heterocycle which has 3 to 7 ring atoms and may optionally by interrupted by further heteroatoms and/or one or two C═O groups, R.sup.2 is the substructure of the general formula —X—Y—Z, where X is phenyl or a 5- or 6-membered heteroaromatic ring, all in each case unsubstituted or substituted by 1 to 3 R.sup.X; wherein each R.sup.X is independently halogen, cyano, nitro, C(Q.sup.1)R.sup.a, C(O)OR.sup.a, C(Q.sup.1)NR.sup.bR.sup.c, NR.sup.dR.sup.e, OR.sup.a, S(O).sub.nR.sup.a or SO.sub.2NR.sup.bR.sup.c; or C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl or C.sub.3-C.sub.7-cycloalkyl, all in each case unsubstituted or substituted by 1 to 7 R.sup.f; Y is —CR.sup.Y1═N—, wherein N is attached to Z, or is —NR.sup.Y2—C(=Q.sup.Y)—, wherein C is attached to Z; wherein each R.sup.Y1 and R.sup.Y2 are H; or C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl or C.sub.3-C.sub.7-cycloalkyl, all in each case unsubstituted or substituted by 1 to 7 R.sup.Y11; wherein each R.sup.Y11 is independently halogen, cyano, C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy or C.sub.1-C.sub.4-haloalkoxy; Q.sup.Y is O or S; Z is a fragment of formula (A1), (A2), (A3) or (A4); ##STR00268## wherein # is the point of attachment to Y and wherein each T is O or S; R.sup.Z1 independently of the others is independently a 5- to 10-membered aromatic or heteroaromatic ring or a bicyclic ring system, in each case unsubstituted or substituted by 1 to 4 R.sup.Z11; wherein each R.sup.Z11 is independently halogen, cyano, nitro, SF.sub.5, C(Q.sup.1)R.sup.a, C(O)OR.sup.a, C(Q.sup.1)NR.sup.bR.sup.c, NR.sup.dR.sup.e, OR.sup.a, S(O).sub.nR.sup.a or SO.sub.2NR.sup.bR.sup.c; or C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl or C.sub.3-C.sub.7-cycloalkyl, all in each case unsubstituted or substituted by 1 to 5 R.sup.Z1a; or phenyl or a 5- or 6-membered heteroaromatic ring, all in each case unsubstituted or substituted by 1 to 3 R.sup.Z1a; or two adjacent R.sup.Z11 together form a straight-chain C.sub.3-C.sub.5-alkylene group which is unsubstituted or substituted by 1 to 6 R.sup.Z1a, wherein independently of one another a CH.sub.2 unit may be replaced by carbonyl and 1 to 2 CH.sub.2 units may be replaced by O, S, NH or N(CH.sub.3); wherein each R.sup.Z1a is halogen, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-thioalkyl, C.sub.1-C.sub.4-haloalkyl or C.sub.1-C.sub.4-haloalkoxy; R.sup.Z2, R.sup.Z2a and R.sup.Z3 independently of one another represent are independently H; or C(O)R.sup.a, C(O)OR.sup.a, C(O)NR.sup.bR.sup.c, S(O).sub.nR.sup.a; or are C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl or C.sub.3-C.sub.7-cycloalkyl, all in each case unsubstituted or substituted by 1 to 5 R.sup.Z21; or phenyl, benzyl or a 5- or 6-membered heteroaromatic ring, all in each case unsubstituted or substituted by 1 to 4 R.sup.Z21; wherein each R.sup.Z21 is independently halogen, cyano, nitro, SF.sub.5, C(Q.sup.1)R.sup.a, C(O)OR.sup.a, C(Q.sup.l)NR.sup.bR.sup.c, NR.sup.dR.sup.e, OR.sup.a, S(O).sub.nR.sup.a or SO.sub.2NR.sup.bR.sup.c; or C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl or C.sub.3-C.sub.7-cycloalkyl; or R.sup.Z2 and R.sup.Z3 together with the T-C—N unit form a 5- to 7-membered ring; wherein the R.sup.Z2—R.sup.Z3 ring members consist of carbon atoms and optionally 1 oxygen or sulfur or nitrogen atom; wherein the heteroatom is not directly attached to T; wherein up to 2 carbon atom ring members independently of one another may consist of C(═O) and C(═S) and the sulfur atom ring member may consist of S, S(O) or S(O).sub.2; wherein this R.sup.Z2—R.sup.Z3 unit is unsubstituted or substituted by 1 to 5 R.sup.Z21; wherein each R.sup.Z21 is independently halogen, cyano, C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy or C.sub.1-C.sub.6-haloalkoxy; or R.sup.Z2a and a second R.sup.Z2a together with the N—C—N unit form a 5- to 7-membered ring; wherein the R.sup.Z2a-R.sup.Z2a ring members consist of carbon atoms and up to 2 heteroatoms which independently of one another may be selected from 1 oxygen atom, 1 sulfur atom and up to 2 nitrogen atoms; wherein up to 2 carbon atom ring members independently of one another may consist of C(═O) and C(═S) and wherein the sulfur atom ring member may consist of S, S(O) or S(O).sub.2; wherein this R.sup.Z2—R.sup.Z3 unit is unsubstituted or substituted by 1 to 5 R.sup.Z21; R.sup.Z41, R.sup.Z42 and R.sup.Z43 are independently H, halogen or NR.sup.dR.sup.e; or are independently C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.7-cycloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.2-C.sub.6-alkenyloxy, C.sub.2-C.sub.6-alkynyloxy, C.sub.3-C.sub.7-cycloalkoxy, C.sub.1-C.sub.6-alkylcarbonyloxy, C.sub.2-C.sub.6-alkenylcarbonyloxy or C.sub.3-C.sub.7-cycloalkylcarbonyloxy, all in each case unsubstituted or substituted by 1 to 7 R.sup.f; or one of the radicals R.sup.Z41, R.sup.Z42 or R.sup.Z43 is oxo; R.sup.Z44 is H; or C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy, C.sub.2-C.sub.6-alkenyloxy, all in each case unsubstituted or substituted by 1 to 5 R.sup.f; wherein each Q.sup.1 is independently O, S, NOR.sup.a or NCN; R.sup.a is independently C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.2-C.sub.6-alkenyl, or C.sub.2-C.sub.6-alkynyl, all of which may in each case be unsubstituted or mono- to tridecasubstituted by halogen and/or optionally substituted by 1 to 3 R.sup.f; or phenyl, unsubstituted or substituted by 1 to 7 R.sup.g; R.sup.b and R.sup.c are independently H; or represent C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.2-C.sub.6-alkenyl or C.sub.2-C.sub.6-alkynyl, all in each case unsubstituted or substituted by 1 to 7 R.sup.f; or phenyl, or a 5- or 6-membered heteroaromatic ring, all in each case unsubstituted or substituted by 1 to 4 R.sup.g; or R.sup.b and R.sup.c together form a 3- to 7-membered ring; R.sup.d and R.sup.e are independently H, C(Q.sup.1)R.sup.a, C(O)OR.sup.a; or represent C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.2-C.sub.6-alkenyl or C.sub.2-C.sub.6-alkynyl, all in each case unsubstituted or substituted by 1 to 7 R.sup.f; or phenyl, unsubstituted or substituted by 1 to 7 R.sup.g; or R.sup.d and R.sup.e together form a 3- to 7-membered ring; R.sup.f is independently halogen, cyano, nitro, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-alkylthio, C.sub.1-C.sub.4-haloalkylthio, 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.1-C.sub.4-alkylcarbonyl or C.sub.1-C.sub.4-alkoxycarbonyl; or phenyl or a 5- or 6-membered heteroaromatic ring, all in each case unsubstituted or substituted by 1 to 7 R.sup.g; R.sup.g is independently halogen, cyano, nitro, C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-alkylthio, C.sub.1-C.sub.4-haloalkylthio, 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.1-C.sub.4-alkylcarbonyl or C.sub.1-C.sub.4-alkoxycarbonyl; R.sup.h is independently halogen, cyano, nitro, hydroxy, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.3-C.sub.6-cycloalkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-alkylthio, C.sub.3-C.sub.6-cycloalkylthio, C.sub.1-C.sub.4-haloalkylthio, C.sub.1-C.sub.4-alkylsulfinyl, C.sub.3-C.sub.6-cycloalkylsulfinyl, C.sub.1-C.sub.4-haloalkylsulfinyl, C.sub.1-C.sub.4-alkylsulfonyl, C.sub.3-C.sub.6-cycloalkylsulfonyl, C.sub.1-C.sub.4-haloalkylsulfonyl, OSO.sub.2R.sup.a, SO.sub.2NR.sup.bR.sup.c, N(R.sup.b)(R.sup.c), C(Q.sup.1)NR.sup.bR.sup.c, N(R.sup.b)C(Q.sup.1)R.sup.a, C(O)R.sup.a, C(O)OR.sup.b OC(O)R.sup.a; or represents phenyl; or a 4- to 7-membered saturated, partially saturated or aromatic heterocycle having 1 to 3 heteroatoms, all in each case unsubstituted or substituted by 1 to 4 R.sup.g; and n is independently 0, 1 or 2.
2. The compound of claim 1, wherein Ar is phenyl, unsubstituted or substituted by 1 to 4 R.sup.Ar; wherein each R.sup.Ar is independently halogen, cyano, nitro, SF.sub.5, C(Q.sup.1)R.sup.a, C(O)OR.sup.a, C(Q.sup.1)NR.sup.bR.sup.c, NR.sup.dR.sup.e, OR.sup.a, S(O).sub.nR.sup.a or SO.sub.2NR.sup.bR.sup.c; or represents C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl or C.sub.3-C.sub.7-cycloalkyl, all of which may in each case be unsubstituted or mono- to tridecasubstituted by halogen and/or optionally by 1 to 2 R.sup.f; or represents phenyl or a 5- or 6-membered heteroaromatic ring, all in each case unsubstituted or substituted by 1 to 3 R.sup.g; A is N or CR.sup.A; wherein R.sup.A is H, halogen, cyano or SF.sub.5; or represents C.sub.1-C.sub.4-alkyl, C.sub.2-C.sub.4-alkenyl or C.sub.3-C.sub.6-cycloalkyl, all of which may in each case be unsubstituted or mono- to heptasubstituted by halogen and/or optionally substituted by 1 R.sup.f; R.sup.1 is NR.sup.11R.sup.12, —N(R.sup.b)OR.sup.a, —N(R.sup.b)—CN, —N(R.sup.11)C(Q.sup.1)R.sup.b, —N(R.sup.11)C(Q.sup.1)NR.sup.bR.sup.c, —N(R.sup.11)C(O)OR.sup.a, —N(R.sup.11)C(O)C(O)R.sup.b, —N(R.sup.11)C(O)C(O)OR.sup.a, —N(R.sup.11)SO.sub.2R.sup.a, —N═C(R.sup.b)N(R.sup.b)(R.sup.c), —N═C(R.sup.b)(R.sup.c); wherein R.sup.11 is H; or represents C.sub.1-C.sub.4-alkyl, C.sub.2-C.sub.4-alkenyl, C.sub.2-C.sub.4-alkynyl or C.sub.3-C.sub.6-cycloalkyl, all of which may be unsubstituted or mono- to pentasubstituted by halogen and/or optionally substituted by 1 to 2 R.sup.h; or phenyl or a heterocycle selected from the group consisting of furanyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl, oxetanyl, oxolanyl, oxanyl, dioxanyl, thiethanyl, thiolanyl, thianyl and dihydroisoxazolyl, in each case unsubstituted or substituted by 1 to 3 R.sup.g; R.sup.12 is H; or C.sub.1-C.sub.4-alkyl, C.sub.2-C.sub.4-alkenyl, C.sub.2-C.sub.4-alkynyl or C.sub.3-C.sub.6-cycloalkyl, all in each case unsubstituted or substituted by 1 to 3 R.sup.g; or R.sup.11 and R.sup.12 together with the nitrogen atom to which they are attached form a heterocycle selected from the group consisting of U-1 to U-30, ##STR00269## ##STR00270## ##STR00271## ##STR00272## wherein U.sup.b is independently halogen, cyano, nitro, C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-alkylthio, C.sub.1-C.sub.4-haloalkylthio, 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.1-C.sub.4-alkylcarbonyl, C.sub.1-C.sub.4-alkoxycarbonyl; and wherein the ring nitrogen atoms in U-13, U-14, U-16 and U-25 are not substituted by halogen, nitro, cyano, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy or C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyloxy; m is 0, 1, 2 or 3, R.sup.2 is the substructure of the general formula —X—Y—Z, wherein X is phenyl, pyridyl, pyrimidyl, pyridazinyl or thienyl, all in each case unsubstituted or substituted by 1 to 3 R.sup.X; where R.sup.X is independently halogen, cyano, nitro, C(Q.sup.1)R.sup.a, C(O)OR.sup.a; or is C.sub.1-C.sub.4-alkyl, C.sub.2-C.sub.4-alkenyl, C.sub.2-C.sub.6-alkynyl or C.sub.3-C.sub.4-cycloalkyl, all in each case unsubstituted or substituted by 1 to 3 R.sup.f; Y is —CR.sup.Y1═N—, wherein N is attached to Z, or is —NR.sup.Y2—C(=Q.sup.Y)—, wherein C is attached to Z; wherein each R.sup.Y1 and R.sup.Y2 are H; or represent are C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl or C.sub.3-C.sub.7-cycloalkyl, all in each case unsubstituted or substituted by 1 to 5 R.sup.Y11; wherein each R.sup.Y11 is independently halogen, cyano, C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy or C.sub.1-C.sub.4-haloalkoxy; Q.sup.Y is O or S; Z is a fragment of formula (A1), (A2), (A3) or (A4); ##STR00273## wherein # is the point of attachment to Y and wherein each T is O or S; R.sup.Z1 is phenyl, unsubstituted or substituted by 1 to 4 R.sup.Z11; wherein each R.sup.Z11 is independently halogen, cyano, nitro, SF.sub.5, C(Q.sup.1)R.sup.a, C(O)OR.sup.a, C(Q.sup.1)NR.sup.bR.sup.c, NR.sup.dR.sup.e, OR.sup.a, S(O).sub.nR.sup.a or SO.sub.2NR.sup.bR.sup.c; or represents C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl or C.sub.3-C.sub.7-cycloalkyl, all in each case unsubstituted or substituted by 1 to 5 R.sup.Z1a; or represents phenyl or a 5- or 6-membered heteroaromatic ring, all in each case unsubstituted or substituted by 1 to 3 R.sup.Z1a; or two adjacent R.sup.Z11 together form a straight-chain C.sub.3-C.sub.5-alkylene group which is unsubstituted or substituted by 1 to 4 R.sup.Z1a wherein independently of one another a CH.sub.2 unit may be replaced by carbonyl and 1 to 2 CH.sub.2 units may be replaced by O, S, NH or N(CH.sub.3); wherein each R.sup.Z1a is halogen, cyano, C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy, C.sub.1-C.sub.3-thioalkyl, C.sub.1-C.sub.3-haloalkyl or C.sub.1-C.sub.3-haloalkoxy; R.sup.Z2, R.sup.Z2a and R.sup.Z3 are independently H; or represent C(O)R.sup.a, C(O)OR.sup.a, C(O)NR.sup.bR.sup.c, S(O).sub.nR.sup.a; or represent C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl or C.sub.3-C.sub.7-cycloalkyl, all in each case unsubstituted or substituted by 1 to 4 R.sup.Z21; or phenyl, benzyl or a 5- or 6-membered heteroaromatic ring, all in each case unsubstituted or substituted by 1 to 3 R.sup.Z21; wherein each R.sup.Z21 is independently halogen, cyano, nitro, SF.sub.5, C(Q.sup.1)R.sup.a, C(O)OR.sup.a, C(Q.sup.1)NR.sup.bR.sup.c, NR.sup.dR.sup.e, OR.sup.a, S(O).sub.nR.sup.a or SO.sub.2NR.sup.bR.sup.c; or represents C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl or C.sub.3-C.sub.7-cycloalkyl; or R.sup.Z2 and R.sup.Z3 together with the T-C—N unit form a 5- to 7-membered ring; wherein the R.sup.Z2-R.sup.Z3 ring members consist of carbon atoms and optionally 1 oxygen or sulfur or nitrogen atom; wherein the heteroatom is not directly attached to T; wherein up to 2 carbon atom ring members independently of one another may consist of C(═O) and C(═S) and the sulfur atom ring member may consist of S, S(O) or S(O).sub.2; wherein this R.sup.Z2-R.sup.Z3 unit is unsubstituted or substituted by 1 to 4 R.sup.Z21; wherein each R.sup.Z21 is independently halogen, cyano, C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy or C.sub.1-C.sub.6-haloalkoxy; or R.sup.Z2a and a second R.sup.Z2a together with the N—C—N unit form a 5- to 7-membered ring; wherein the R.sup.Z2a-R.sup.Z2a ring members consist of carbon atoms and up to 2 heteroatoms which independently of one another may be selected from 1 oxygen atom, 1 sulfur atom and up to 2 nitrogen atoms; wherein up to 2 carbon atom ring members independently of one another may consist of C(═O) and C(═S) and wherein the sulfur atom ring member may consist of S, S(O) or S(O).sub.2; wherein this R.sup.Z2—R.sup.Z3 unit is unsubstituted or substituted by 1 to 4 R.sup.Z21; R.sup.Z41, R.sup.Z42 and R.sup.Z43 are independently H, halogen or NR.sup.dR.sup.e; or represent C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.7-cycloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.2-C.sub.6-alkenyloxy, C.sub.2-C.sub.6-alkynyloxy, C.sub.3-C.sub.7-cycloalkoxy, C.sub.1-C.sub.6-alkylcarbonyloxy, C.sub.2-C.sub.6-alkenylcarbonyloxy or C.sub.3-C.sub.7-cycloalkylcarbonyloxy, all in each case unsubstituted or substituted by 1 to 7 R.sup.f; or one of the radicals R.sup.Z41, R.sup.Z42 or R.sup.Z43 is oxo; R.sup.Z44 is H; or C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy, C.sub.2-C.sub.6-alkenyloxy, all in each case unsubstituted or substituted by 1 to 5 R.sup.f, wherein each Q.sup.1 is independently 0, S, NOR.sup.a or NCN; R.sup.a is independently C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.2-C.sub.6-alkenyl or C.sub.2-C.sub.6-alkynyl, all of which may in each case be unsubstituted or mono- to tridecasubstituted by halogen and/or optionally substituted by 1 R.sup.f; or phenyl, unsubstituted or substituted by 1 to 5 R.sup.g; R.sup.b and R.sup.c are independently H; or C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, all in each case unsubstituted or substituted by 1 to 5 R.sup.f; or phenyl, or a heteroaromatic ring selected from the group consisting of pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl, pyridyl and pyrimidyl, all in each case unsubstituted or substituted by 1 to 5 R.sup.g; or R.sup.b and R.sup.c together form a 3- to 7-membered ring; R.sup.d and R.sup.e are independently H, C(Q.sup.1)R.sup.a, C(O)OR.sup.a; or represent C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.2-C.sub.6-alkenyl or C.sub.2-C.sub.6-alkynyl, all in each case unsubstituted or substituted by 1 to 5 R.sup.f; or phenyl, unsubstituted or substituted by 1 to 5 R.sup.g; or R.sup.d and R.sup.e together form a 3- to 7-membered ring; R.sup.f is independently halogen, cyano, nitro, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-alkylthio, C.sub.1-C.sub.4-haloalkylthio, 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.1-C.sub.4-alkylcarbonyl or C.sub.1-C.sub.4-alkoxycarbonyl; or phenyl or a 5- or 6-membered heteroaromatic ring, all in each case unsubstituted or substituted by 1 to 5 R.sup.g; R.sup.g is independently halogen, cyano, nitro, C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-alkylthio, C.sub.1-C.sub.4-haloalkylthio, 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.1-C.sub.4-alkylcarbonyl or C.sub.1-C.sub.4-alkoxycarbonyl; R.sup.h is independently halogen, cyano, nitro, hydroxy, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.3-C.sub.6-cycloalkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-alkylthio, C.sub.3-C.sub.6-cycloalkylthio, C.sub.1-C.sub.4-haloalkylthio, C.sub.1-C.sub.4-alkylsulfinyl, C.sub.3-C.sub.6-cycloalkylsulfinyl, C.sub.1-C.sub.4-haloalkylsulfinyl, C.sub.1-C.sub.4-alkylsulfonyl, C.sub.3-C.sub.6-cycloalkylsulfonyl, C.sub.1-C.sub.4-haloalkylsulfonyl, OSO.sub.2R.sup.a, SO.sub.2NR.sup.bR.sup.c, N(R.sup.b)(R.sup.c), C(Q.sup.1)NR.sup.bR.sup.e, N(R.sup.b)C(Q.sup.1)R.sup.a, C(O)R.sup.a, C(O)OR.sup.b OC(O)R.sup.a; or phenyl or a heterocycle selected from the group consisting of furanyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl, oxetanyl, oxolanyl, dioxolanyl, oxanyl, dioxanyl, thiethanyl, thiolanyl, thianyl and dihydroisoxazolyl, all in each case unsubstituted or substituted by 1 to 3 R.sup.g; and n is independently 0, 1 or 2.
3. The compound of claim 1, wherein Ar is phenyl, unsubstituted or substituted by 1 to 4 R.sup.Ar; wherein each R.sup.Ar is independently halogen, SF.sub.5, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy or C.sub.1-C.sub.4-haloalkoxy; A is N or CR.sup.A; wherein R.sup.A is H; R.sup.1 is NR.sup.11R.sup.12, —N(R.sup.b)OR.sup.a, —N(R.sup.b)—CN, —N(R.sup.11)C(Q.sup.1)R.sup.b, —N(R.sup.11)C(Q.sup.1)NR.sup.bR.sup.c, —N(R.sup.11)C(O)OR.sup.a, —N(R.sup.11)C(O)C(O)OR.sup.a, —N(R.sup.11)SO.sub.2R.sup.a, —N═C(R.sup.b)N(R.sup.b)(R.sup.c); wherein R.sup.11 is H; or C.sub.1-C.sub.4-alkyl, C.sub.2-C.sub.4-alkenyl, C.sub.2-C.sub.4-alkynyl or C.sub.3-C.sub.6-cycloalkyl, all of which may be unsubstituted or mono- to pentasubstituted by halogen and/or optionally substituted by 1 to 2 R.sup.b; or phenyl or a heterocycle selected from the group consisting of furanyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl, pyridyl, pyrimidyl, oxetanyl, oxolanyl, oxanyl, and thiethanyl, all in each case unsubstituted or substituted by 1 to 3 R.sup.g; R.sup.12 is H; or represents C.sub.1-C.sub.4-alkyl, C.sub.2-C.sub.4-alkenyl, C.sub.2-C.sub.4-alkynyl or C.sub.3-C.sub.6-cycloalkyl, all in each case unsubstituted or substituted by 1 to 3 R.sup.g; or R.sup.11 and R.sup.12 together with the nitrogen atom to which they are attached represent form a heterocycle selected from the group consisting of U-1 to U-7; U-13, U-14 and U-22 to U-27, ##STR00274## ##STR00275## wherein U.sup.b is independently halogen, cyano, nitro, C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-alkylthio, C.sub.1-C.sub.4-haloalkylthio, 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; and wherein the ring nitrogen atoms in U-13, U-14 and U-25 are not substituted by halogen, nitro, cyano, C.sub.1-C.sub.4-alkoxy or C.sub.1-C.sub.4-haloalkoxy; m is 0, 1 or 2, R.sup.2 is the substructure of the general formula —X—Y—Z, where X is phenyl, pyridyl or thienyl, all in each case unsubstituted or substituted by 1 to 3 R.sup.X; wherein each R.sup.X is independently halogen, cyano, nitro; or C.sub.1-C.sub.4-alkyl, in each case unsubstituted or substituted by 1 to 3 R.sup.f; Y is CR.sup.Y1═N, wherein N is attached to Z, or is —NR.sup.Y2—C(=Q.sup.Y)—, wherein C is attached to Z; wherein each R.sup.Y1 and R.sup.Y2 is H; or C.sub.1-C.sub.2-alkyl or C.sub.3-C.sub.6-cycloalkyl, all in each case unsubstituted or substituted by 1 to 3 R.sup.Y11; wherein each R.sup.Y11 is independently halogen, cyano, C.sub.1-C.sub.2-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.2-haloalkyl, C.sub.1-C.sub.2-alkoxy or C.sub.1-C.sub.2-haloalkoxy; Q.sup.Y is O or S; Z is a fragment of formula (A1), (A2), (A3) or (A4); ##STR00276## wherein # is the point of attachment to Y and wherein each T is O or S; R.sup.Z1 is phenyl, substituted by 1 to 4 R.sup.Z11; wherein each R.sup.Z11 is independently halogen, cyano, OR.sup.a, SR.sup.a; or represents C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, all in each case unsubstituted or substituted by 1 to 3 R.sup.Z1a; or two adjacent R.sup.Z11 together form a straight-chain C.sub.3-C.sub.5-alkylene group which is unsubstituted or substituted by 1 to 4 R.sup.Z1a, wherein independently of one another 1 CH.sub.2 unit may be replaced by carbonyl and 1 to 2 CH.sub.2 units may be replaced by O, S, NH or N(CH.sub.3); wherein each R.sup.Z1a is halogen, cyano, C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy, C.sub.1-C.sub.3-thioalkyl, C.sub.1-C.sub.3-haloalkyl or C.sub.1-C.sub.3-haloalkoxy; R.sup.Z2, R.sup.Z2a and R.sup.Z3 are independently H; or represent C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl or C.sub.3-C.sub.7-cycloalkyl, all in each case unsubstituted or substituted by 1 to 4 R.sup.Z21; or represent phenyl or benzyl, all in each case unsubstituted or substituted by 1 to 3 R.sup.Z21; R.sup.Z21 is independently halogen, cyano, C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy or C.sub.1-C.sub.4-haloalkoxy; or R.sup.Z2 and R.sup.Z3 together with the T-C—N unit form a 5- to 7-membered ring; wherein the R.sup.Z2-R.sup.Z3 ring members consist of carbon atoms and optionally 1 oxygen or sulfur or nitrogen atom; wherein the heteroatom is not directly attached to T; wherein up to 2 carbon atom ring members independently of one another may consist of C(═O) and C(═S) and the sulfur atom ring member may consist of S, S(O) or S(O).sub.2; wherein this R.sup.Z2-R.sup.Z3 unit is unsubstituted or substituted by 1 to 3 R.sup.Z21; wherein each R.sup.Z21 is independently halogen, cyano, C.sub.1-C.sub.3-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.3-haloalkyl, C.sub.1-C.sub.3-alkoxy or C.sub.1-C.sub.3-haloalkoxy; R.sup.Z41, R.sup.Z42 and R.sup.Z43 are independently C.sub.1-C.sub.4-alkoxy or C.sub.2-C.sub.4-alkenyloxy; R.sup.Z44 is H or C.sub.1-C.sub.4-alkyl, wherein each Q.sup.1 is independently O or S; R.sup.a is independently C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.2-C.sub.4-alkenyl or C.sub.2-C.sub.4-alkynyl, all of which may in each case be unsubstituted or mono- to heptasubstituted by halogen and/or optionally substituted by 1 R.sup.f; R.sup.b and R.sup.c are independently H; or represent C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.2-C.sub.4-alkenyl, C.sub.2-C.sub.4-alkynyl, all in each case unsubstituted or substituted by 1 to 3 R.sup.f; R.sup.f is independently halogen, cyano, nitro, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-alkylthio, C.sub.1-C.sub.4-haloalkylthio, 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.1-C.sub.4-alkylcarbonyl or C.sub.1-C.sub.4-alkoxycarbonyl; or phenyl or a 5- or 6-membered heteroaromatic ring, all in each case unsubstituted or substituted by 1 to 3 R.sup.g; R.sup.g is independently halogen, cyano, nitro, C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-alkylthio, C.sub.1-C.sub.4-haloalkylthio, 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.1-C.sub.4-alkylcarbonyl or C.sub.1-C.sub.4-alkoxycarbonyl; and R.sup.h is independently halogen, cyano, nitro, hydroxy, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.3-C.sub.6-cycloalkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-alkylthio, C.sub.3-C.sub.6-cycloalkylthio, C.sub.1-C.sub.4-haloalkylthio, C.sub.1-C.sub.4-alkylsulfinyl, C.sub.3-C.sub.6-cycloalkylsulfinyl, C.sub.1-C.sub.4-haloalkylsulfinyl, C.sub.1-C.sub.4-alkylsulfonyl, C.sub.3-C.sub.6-cycloalkylsulfonyl, C.sub.1-C.sub.4-haloalkylsulfonyl, C(Q.sup.1)NR.sup.bR.sup.c, N(R.sup.b)C(Q.sup.1)R.sup.a; or phenyl or a heterocycle selected from the group consisting of furanyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyrimidyl, oxetanyl, oxolanyl, dioxolanyl, oxanyl, dioxanyl, and thiethanyl, all in each case unsubstituted or substituted by 1 to 3 R.sup.g.
4. The compound of claim 1, wherein Ar is phenyl, unsubstituted or substituted by 1 to 3 R.sup.Ar; wherein each R.sup.Ar is independently halogen, SF.sub.5, CF.sub.3, OCF.sub.3, OCH.sub.2CF.sub.3 or OCF.sub.2CF.sub.3; A is N or CR.sup.A; wherein R.sup.A is H; R.sup.1 is NR.sup.11R.sup.12, —N(R.sup.b)OR.sup.a, —N(R.sup.b)—CN, —N(R.sup.11)C(Q.sup.1)R.sup.b, —N(R.sup.11)C(Q.sup.1)NR.sup.bR.sup.c, —N(R.sup.11)C(O)OR.sup.a, —N(R.sup.11)C(O)C(O)OR.sup.a, —N(R.sup.11)SO.sub.2R.sup.a, —N═C(R.sup.b)N(R.sup.b)(R.sup.c); where R.sup.11 is H; or C.sub.1-C.sub.4-alkyl, C.sub.2-C.sub.4-alkenyl, C.sub.2-C.sub.4-alkynyl or C.sub.3-C.sub.6-cycloalkyl, all of which may be unsubstituted or mono- to trisubstituted by halogen and/or optionally substituted by 1 to 2 R.sup.b; or a heterocycle selected from the group consisting of pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, pyridyl, pyrimidyl, oxetanyl, oxolanyl, oxanyl, and thiethanyl, all in each case unsubstituted or substituted by 1 to 3 R.sup.g; R.sup.12 is H; or represents C.sub.1-C.sub.4-alkyl, C.sub.2-C.sub.4-alkenyl, C.sub.2-C.sub.4-alkynyl or C.sub.3-C.sub.6-cycloalkyl, all in each case unsubstituted or substituted by 1 to 3 R.sup.g; or R.sup.11 and R.sup.12 together with the nitrogen atom to which they are attached represent form a heterocycle selected from the group consisting of (U-2), (U-3), (U-6), (U-22), (U-23), (U-24), (U-25), (U-26) and (U-27), ##STR00277## wherein U.sup.b is independently halogen, cyano, nitro, C.sub.1-C.sub.4-alkyl or C.sub.1-C.sub.4-alkoxy; and wherein the ring nitrogen atoms in U-25 are not substituted by halogen, nitro, cyano, C.sub.1-C.sub.4-alkoxy or C.sub.1-C.sub.4-haloalkoxy; m is 0 or 1, R.sup.2 is the substructure of the general formula —X—Y—Z, where X is phenyl or pyridyl, unsubstituted or substituted by 1 to 3 R.sup.X; wherein each R.sup.X is independently halogen, cyano or methyl; Y is CR.sup.Y1═N, wherein N is attached to Z, or —NR.sup.Y2—C(=Q.sup.Y)—, wherein C is attached to Z; wherein each R.sup.Y1 and R.sup.Y2 is H, CH.sub.3 or CH.sub.2CH.sub.3; Q.sup.Y is O or S; Z is a fragment of formula (A1), (A2), (A3) or (A4); ##STR00278## wherein # is the point of attachment to Y and wherein each T is O or S; R.sup.Z1 is phenyl, substituted by 1 to 4 R.sup.Z11; wherein 1 R.sup.Z11 is located in the 2-position and wherein each R.sup.Z11 is independently F, C.sub.1, Br, CH.sub.3, CH.sub.2CH.sub.3, CH.sub.2CH.sub.2CH.sub.3, CH(CH.sub.3).sub.2, CH.sub.2CH.sub.2CH.sub.2CH.sub.3, cyclopropyl, OCH.sub.3, OCH.sub.2CH.sub.3, OCH.sub.2CH.sub.2CH.sub.3, OCH(CH.sub.3).sub.2, CH.sub.2OCH.sub.3 or CH(CH.sub.3)OCH.sub.3; R.sup.Z2, R.sup.Z2a and R.sup.Z3 are independently H; or R.sup.Z2 and R.sup.Z3 together with the T-C—N unit form a 5- to 7-membered ring; wherein the R.sup.Z2-R.sup.Z3 ring members consist of carbon atoms and optionally 1 oxygen or sulfur or nitrogen atom; wherein the heteroatom is not directly attached to T; wherein up to 2 carbon atom ring members independently of one another may consist of C(═O) and C(═S) and the sulfur atom ring member may consist of S, S(O) or S(O).sub.2; wherein this R.sup.Z2—R.sup.Z3 unit is unsubstituted or substituted by 1 to 3 R.sup.Z21; wherein each R.sup.Z21 is halogen, cyano, C.sub.1-C.sub.3-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.3-haloalkyl, C.sub.1-C.sub.3-alkoxy or C.sub.1-C.sub.3-haloalkoxy; R.sup.Z41 is OCH.sub.3 or OCH.sub.2CH.sub.3; R.sup.Z42 is OCH.sub.3, OCH.sub.2CH.sub.3 or OCH.sub.2CH.sub.2CH.sub.3; R.sup.Z43 is OCH.sub.3 or OCH.sub.2CH.sub.3; R.sup.Z44 is CH.sub.3; wherein each Q.sup.1 is independently O or S; R.sup.a is independently C.sub.1-C.sub.4-alkyl or C.sub.3-C.sub.6-cycloalkyl, all of which may in each case be unsubstituted or mono- to heptasubstituted by halogen and/or may be substituted by 1 R.sup.f; R.sup.b and R.sup.c are independently H; or represent C.sub.1-C.sub.4-alkyl or C.sub.3-C.sub.4-cycloalkyl, all in each case unsubstituted or substituted by 1 to 3 R.sup.f; R.sup.f is independently halogen, cyano, nitro, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-alkylthio, C.sub.1-C.sub.4-alkylsulfinyl, C.sub.1-C.sub.4-alkylsulfonyl, C.sub.1-C.sub.4-alkylcarbonyl, C.sub.1-C.sub.4-alkoxycarbonyl; R.sup.g is independently halogen, cyano, nitro, C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-alkylthio, C.sub.1-C.sub.4-alkylsulfinyl, C.sub.1-C.sub.4-alkylsulfonyl; and R.sup.h is independently halogen, cyano, nitro, hydroxy, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.3-C.sub.6-cycloalkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-alkylthio, C.sub.1-C.sub.4-alkylsulfinyl, C.sub.3-C.sub.6-cycloalkylsulfinyl, C.sub.1-C.sub.4-alkylsulfonyl, C(Q.sup.1)NR.sup.bR.sup.c, N(R.sup.b)C(Q.sup.1)R.sup.a; or is a heterocycle selected from the group consisting of pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, pyridyl, pyrimidyl, oxetanyl, oxolanyl, dioxolanyl, oxanyl, dioxanyl, and thiethanyl, all in each case unsubstituted or substituted by 1 to 3 R.sup.g.
5. The compound of claim 1, wherein Ar is phenyl, unsubstituted or substituted by 1 to 2 R.sup.Ar; wherein each R.sup.Ar is independently fluorine, chlorine, SF.sub.5, CF.sub.3, OCF.sub.3 or OCF.sub.2CF.sub.3; A is N or CR.sup.A; wherein R.sup.A is H; R.sup.1 is NR.sup.11R.sup.12, —N(R.sup.b)OR.sup.a, —N(R.sup.b)—CN, —N(R.sup.11)C(O)R.sup.b, —N(R.sup.11)C(O)NR.sup.bR.sup.c, —N(R.sup.11)C(O)OR.sup.a, —N(R.sup.11)C(O)C(O)OR.sup.a, —N(R.sup.11)SO.sub.2R.sup.a, —N═C(R.sup.b)N(R.sup.b)(R.sup.c); wherein R.sup.11 is H; or is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclopropyl, cyclobutyl, ethenyl or propenyl, all of which may in each case be unsubstituted or mono- to trisubstituted by halogen and/or optionally substituted by 1 or 2 R.sup.h; or a heterocycle selected from the group consisting of oxan-4-yl, oxolan-3-yl, thietan-3-yl, and oxetan-3-yl, all of which in each case unsubstituted or substituted by 1 R.sup.g; R.sup.12 is H; or methyl or ethyl; or R.sup.11 and R.sup.12 together with the nitrogen atom to which they are attached form a heterocycle selected from the group consisting of (U-3), (U-6) and (U-23); ##STR00279## wherein U.sup.b is independently fluorine, chlorine, methyl, ethyl, methoxy or ethoxy; m is 0 or 1, R.sup.2 is the substructure of the general formula —X—Y—Z, wherein X is phenyl or pyridyl, unsubstituted or substituted by 1 to 2 R.sup.X; where R.sup.X is independently halogen, cyano or methyl; Y is —CR.sup.Y1═N—, wherein N is attached to Z, or is —NR.sup.Y2—C(=Q.sup.Y)—, wherein C is attached to Z; wherein each R.sup.Y1 is H or CH.sub.3; R.sup.Y2 is H; Q.sup.Y is O or S; Z is a fragment of formula (A1), (A2), (A3), (A4-1) or (A4-2); ##STR00280## wherein # is the point of attachment to Y and wherein each T is S; R.sup.Z1 is phenyl, substituted by 1 to 4 R.sup.Z11; wherein 1 R.sup.Z11 is located in the 2-position and wherein each R.sup.Z11 is independently F, C.sub.1, Br, CH.sub.3, CH.sub.2CH.sub.3, CH.sub.2CH.sub.2CH.sub.3, CH(CH.sub.3).sub.2, CH.sub.2CH.sub.2CH.sub.2CH.sub.3, cyclopropyl, OCH.sub.3, OCH.sub.2CH.sub.3, OCH.sub.2CH.sub.2CH.sub.3, OCH(CH.sub.3).sub.2 or CH.sub.2OCH.sub.3; R.sup.Z2, R.sup.Z2a and R.sup.Z3 are H; or R.sup.Z2 and R.sup.Z3 together form —C(O)CH.sub.2—, —C(O)CH(CH.sub.3)—, —C(O)CH.sub.2CH.sub.2—, —CH.sub.2C(O)CH.sub.2—, —CH.sub.2CH.sub.2—, —CH.sub.2CH.sub.2CH.sub.2— or —C(Me)=CH—; R.sup.Z45 is CH.sub.3 or C.sub.2H.sub.5; wherein each R.sup.a is independently methyl, ethyl, n-propyl, isopropyl or cyclopropyl, all of which may in each case be unsubstituted, mono- to pentasubstituted by halogen and/or optionally substituted by 1 R.sup.f; R.sup.b and R.sup.c are independently H; or represent methyl, ethyl, n-propyl, isopropyl or cyclopropyl, all in each case unsubstituted or substituted by 1 to 3 R.sup.f; R.sup.f is independently fluorine, chlorine, cyano, methoxy or ethoxy; R.sup.g is independently fluorine, chlorine, cyano, methoxy or ethoxy; and R.sup.h is independently fluorine, chlorine, cyano, hydroxy, methoxy, ethoxy, NHCOCH.sub.3, NHCOCH.sub.2CH.sub.3, —SO.sub.2CH.sub.3.
6. The compound of claim 1, wherein Ar is phenyl substituted in the 4-position by OCF.sub.3 or OCF.sub.2CF.sub.3; A is N or CR.sup.A; wherein R.sup.A is H; R.sup.1 is —NR.sup.11R.sup.12, —N(CH.sub.3)OCH.sub.3, —NH—CN, —NHC(O)CH.sub.3, —NHC(O)CH.sub.2CH.sub.3, —NHC(O)-cyclopropyl, —NHC(O)CHF.sub.2, —NHC(O)NHCH.sub.3, —NHC(O)OCH.sub.2CH.sub.3, —NHC(O)C(O)OCH.sub.2CH.sub.3, —NHSO2CH.sub.3, —NHSO.sub.2CH.sub.2CH.sub.3, —NHSO.sub.2-cyclopropyl, —NHSO.sub.2CHF.sub.2 or —N═CHN(CH.sub.3)(CH.sub.3); wherein R.sup.11 is H; or represents methyl, ethyl, isopropyl, cyclopropyl, cyclobutyl, 2-(acetamid)ethyl, 2-ethoxyethyl, oxolan-3-yl, thietan-3-yl, oxetan-3-yl, propen-2-yl, 2-methoxyethyl, 2,2-diethoxyethyl, oxan-4-yl, 3-methoxypropyl, 2-hydroxyethyl, 3,3-dimethoxypropyl, 2-cyanoethyl or 2-methylsulfonylethyl, R.sup.12 is H; or methyl or ethyl; or R.sup.11 and R.sup.12 together with the nitrogen atom to which they are attached form (U-3-1) or (U-23-1); ##STR00281## R.sup.2 is the substructure of the general formula —X—Y—Z, wherein X is phenyl, unsubstituted or substituted by 1 to 2 R.sup.X, or pyrid-2-yl; wherein R.sup.X is independently fluorine, chlorine, cyano or methyl; Y is CR.sup.Y1═N, wherein N is attached to Z, or is —NR.sup.Y2—C(=Q.sup.Y)—, wherein C is attached to Z; wherein each R.sup.Y1 is H or CH.sub.3; R.sup.Y2 is H; Q.sup.Y is O; Z is a fragment of formula (A2-1), (A3-1) or (A4-1); ##STR00282## wherein # is the point of attachment to Y and wherein each R.sup.Z1 is phenyl, substituted by 1 to 2 R.sup.Z11; wherein 1 R.sup.Z11 is located in the 2-position and wherein each RZ.sup.11 is independently OCH.sub.3, CH.sub.3 or isopropyl; and R.sup.Z45 is CH.sub.3 or C.sub.2H.sub.5.
7. A formulation comprising at least one compound of the formula (I) according to claim 1.
8. The formulation of claim 7, further comprising at least one extender and/or at least one surface-active substance.
9. The formulation of claim 7, wherein the compound of the formula (I) is in a mixture with at least one further active compound.
10. A method for controlling pests, comprising applying a compound of formula (I) according to claim 1, to the pests and/or their habitat.
11. The method of claim 10, wherein the pests are animal pests and comprise an insect, an arachnid or a nematode, or wherein the pests are insects, arachnids or nematodes.
12. A method for controlling pests, comprising applying a formulation according to claim 7, to the pests and/or their habitat.
13. The method of claim 12, wherein the pests are animal pests and comprise an insect, an arachnid or a nematode, or wherein the pests are insects, arachnids or nematodes.
14. A method for controlling animal pests in crops, comprising applying a compound of formula (I) directly to the crop plant or crop plant parts, or to their surroundings, habitat or storage space.
15. A method for protecting seed or a germinating plant from pests, comprising contacting the seed with a compound of formula (I) according to claim 1.
16. A seed obtained by a method according to claim 15.
17. The method of claim 15, wherein the pests are animal pests.
Description
PREPARATION EXAMPLES
Preparation of 3,5-dibromo-1-[4-(trifluoromethoxy)phenyl]-1H-1,2,4-triazole (IM-1a, process U)
[0703] ##STR00051##
[0704] 3,5-Dibromo-1H-1,2,4-triazole (5.00 g, 22.0 mmol), [4-(trifluoromethoxy)phenyl]boronic acid (4.54 g, 22.0 mmol) and copper(II) acetate monohydrate (6.60 g, 33.1 mmol) were initially charged in toluene (50 ml), and pyridine (5.23 g, 66.1 mmol) and 4 A molecular sieve (1.0 g) were added. The mixture was then stirred at 80° C. for 16 h. The reaction mixture was filtered through Celite, the filter cake was washed with ethyl acetate and the organic phase was washed with water. After drying over magnesium sulfate, the solvent was distilled off under reduced pressure and the residue was separated chromatographically on silica gel (gradient: dichloromethane/ethyl acetate). This gave 1.70 g of 3,5-dibromo-1-[4-(trifluoromethoxy)phenyl]-1H-1,2,4-triazole.
[0705] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 7.63 (d, 1H), 7.84 (d, 2H).
[0706] The following was prepared analogously to (IM-1a):
3,5-Dibromo-1-[1,1,2,2,2-pentafluoroethoxy)phenyl]-1H-1,2,4-triazole (IM-1b)
[0707] ##STR00052##
[0708] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 7.65 (d, 1H), 7.85 (d, 2H).
Preparation of 5-bromo-N-methyl-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazole-3-amine (IM-2a, process Q)
[0709] ##STR00053##
[0710] 3,5-Dibromo-1-[4-(trifluoromethoxy)phenyl]-1H-1,2,4-triazole (IM-1a) (500 mg, 1.29 mmol) was dissolved in ethanol (8 ml), and a 33% strength ethanolic methylamine solution (1.13 ml, 12.9 mmol) was added. The mixture was then stirred at room temperature for 16 h. The reaction mixture was poured into water and extracted with dichloromethane. After drying over magnesium sulfate, the solvent was distilled off under reduced pressure and the residue was separated chromatographically on silica gel (gradient: dichloromethane/ethyl acetate). This gave 435 mg of 5-bromo-N-methyl-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-amine.
[0711] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 2.80 (d, 3H), 6.98 (m, 1H), 7.52 (d, 2H), 7.64 (d, 2H).
[0712] The following were prepared analogously to (IM-2a):
5-Bromo-N-cyclopropyl-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-amine (IM-2b)
[0713] ##STR00054##
[0714] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 0.52 (m, 2H), 0.64 (m, 2H), 2.62 (m, 1H), 7.32 (m, 1H), 7.51 (d, 2H), 7.62 (d, 2H).
5-Bromo-N,N-diethyl-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-amine (IM-2c)
[0715] ##STR00055##
[0716] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 0.97 (t, 6H), 3.11 (q, 4H), 7.54 (d, 2H), 7.71 (d, 2H).
4-[5-Bromo-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]morpholine (IM-2d)
[0717] ##STR00056##
[0718] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 3.07 (m, 4H), 3.62 (m, 4H), 7.54 (d, 2H), 7.77 (d, 2H).
5-Bromo-N-ethyl-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-amine (IM-2e)
[0719] ##STR00057##
[0720] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 0.99 (t, 6H), 3.13 (q, 4H), 7.20 (m, 1H), 7.55 (d, 2H), 7.72 (d, 2H).
N-[2-[[5-Bromo-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]amino]ethyl]acetamide (IM-2f)
[0721] ##STR00058##
[0722] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 1.78 (s, 3H), 3.22-3.33 (m, 4H), 7.14 (m, 1H), 7.52 (d, 2H), 7.64 (d, 2H), 7.96 (m, 1H).
5-Bromo-N-methoxy-N-methyl-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-amine (IM-2g)
[0723] ##STR00059##
[0724] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 3.08 (s, 3H), 3.12 (s, 3H), 7.64 (d, 2H), 7.82 (d, 2H).
5-Bromo-N-cyclobutyl-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-amine (IM-2h)
[0725] ##STR00060##
[0726] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 1.64 (m, 2H), 2.04 (m, 2H), 2.18 (m, 2H), 4.13 (m, 1H), 7.27 (m, 1H), 7.52 (d, 2H), 7.64 (d, 2H).
5-Bromo-N-(2-methylethyl)-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-amine (IM-2i)
[0727] ##STR00061##
[0728] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 1.16 (d, 6H), 3.85 (m, 1H), 6.83 (m, 1H), 7.52 (m, 2H), 7.64 (d, 2H).
5-Bromo-N-(2-ethoxyethyl)-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-amine (IM-2j)
[0729] ##STR00062##
[0730] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 1.09 (t, 3H), 3.41-3.51 (m, 6H), 7.09 (m, 1H), 7.55 (d, 2H), 7.63 (d, 2H).
5-Bromo-N-2-oxetanyl-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-amine (IM-2k)
[0731] ##STR00063##
[0732] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 4.56 (m, 2H), 4.75 (m, 3H), 7.54 (m, 2H), 7.70 (d, 2H), 7.82 (m, 1H).
5-Bromo-N-2-tetrahydrofuran-3-yl-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-amine (IM-21)
[0733] ##STR00064##
[0734] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 1.92 (m, 1H), 2.15 (m, 1H), 3.60 (m, 1H), 3.65 (m, 1H), 3.82 (m, 2H), 4.25 (m, 1H), 7.18 (m, 1H), 7.54 (d, 2H), 7.64 (d, 2H).
5-Bromo-N-2-thietanyl-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-amine (IM-2m)
[0735] ##STR00065##
[0736] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 3.24 (m, 2H), 3.49 (m, 2H), 4.94 (m, 1H), 7.54 (m, 2H), 7.68 (d, 2H), 7.75 (m, 1H).
5-Bromo-N-methyl-2-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1,2,4-triazol-3-amine (IM-2n)
[0737] ##STR00066##
[0738] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 2.83 (d, 3H), 7.21 (m, 1H), 7.54 (d, 2H), 7.66 (d, 2H).
Preparation of 5-bromo-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazole-3-amine (IM-3a, Process Q)
[0739] ##STR00067##
[0740] 3,5-Dibromo-1-[4-(trifluoromethoxy)phenyl]-1H-1,2,4-triazole (IM-1) (1250 mg, 3.23 mmol) was dissolved in dioxane (12 ml), and 12.8 ml (220 mmol) of a 33% strength aqueous ammonia solution were added. The mixture was then stirred at 80-90° C. for 16 h. The dioxane was distilled off and the precipitated solid was filtered off with suction. The crude product was purified chromatographically on silica gel (gradient: dichloromethane/ethyl acetate). This gave 648 mg of 5-bromo-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-amine.
[0741] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 6.91 (s, 2H), 7.53 (d, 2H), 7.65 (d, 2H).
Preparation of N-[5-bromo-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]acetamide (IM-4a, Process N-2)
[0742] ##STR00068##
[0743] 5-Bromo-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-amine (IM-3a) (100 mg, 0.31 mmol) was dissolved in dichloroethane (2 ml), and pyridine (540 mg, 0.68 mmol) and then acetyl chloride (54 mg, 0.68 mmol) were added. The mixture was then stirred at 60° C. for 16 h. The reaction mixture was taken up in dichloromethane/water and filtered through a Chromabond™ PTS separation column. The crude product was purified chromatographically on silica gel (gradient: dichloromethane/ethyl acetate). This gave 87 mg of N-[5-bromo-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]acetamide.
[0744] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 2.00 (s, 3H), 7.53 (d, 2H), 7.66 (d, 2H), 10.88 (s, 1H).
Preparation of N-[5-bromo-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]methanesulfonamide (IM-5a, Process S)
[0745] ##STR00069##
[0746] 3,5-Dibromo-1-[4-(trifluoromethoxy)phenyl]-1H-1,2,4-triazole (IM-1a) (500 mg, 1.29 mmol) was dissolved in dimethylformamide (9.5 ml), and first methylsulfonamide (152 mg, 1.55 mmol) and then potassium carbonate (535 mg, 3.87 mmol) were added. The mixture was then stirred at 80-90° C. for 16 h. The reaction mixture was poured onto water and acidified with 10% strength hydrochloric acid, and the resulting precipitate was filtered off with suction and dried. The crude product was purified chromatographically on silica gel (gradient: cyclohexane/ethyl acetate). This gave 261 mg of N-[5-bromo-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]methanesulfonamide.
[0747] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 3.00 (s, 3H), 7.54 (d, 2H), 7.98 (d, 2H).
[0748] The following were obtained analogously to (IM-5a):
N-[5-Bromo-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]ethanesulfonamide (IM-5b)
[0749] ##STR00070##
[0750] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 1.25 (t, 3H), 3.34 (q, 3H), 7.60 (d, 2H), 7.82 (d, 2H).
N-[5-Bromo-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]cyclopropanesulfonamide (IM-5c)
[0751] ##STR00071##
[0752] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 0.54 (m, 2H), 0.63 (m, 2H), 3.45 (m, 1H), 7.58 (d, 2H), 7.80 (d, 2H).
N-[5-Bromo-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]-1,1-difluoromethanesulfonamide (IM-5d)
[0753] ##STR00072##
[0754] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 6.73 (t, 1H), 7.44 (d, 2H), 7.99 (d, 2H).
Preparation of 3-bromo-5-imidazol-1-yl-1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazole (IM-6a, Process Q)
[0755] ##STR00073##
[0756] 3,5-Dibromo-1-[4-(trifluoromethoxy)phenyl]-1H-1,2,4-triazole (IM-1a) (250 mg, 0.64 mmol) was dissolved in dimethylformamide (5.9 ml), and first imidazole (53 mg, 0.77 mmol) and then potassium carbonate (268 mg, 1.93 mmol) were added. The mixture was then stirred at 80-90° C. for 16 h. The reaction mixture was poured onto water, acidified with 10% strength hydrochloric acid, extracted with dichloromethane and dried over magnesium sulfate, and the solvent was distilled off. The crude product was purified chromatographically on silica gel (gradient: cyclohexane/ethyl acetate). This gave 174 mg of 3-bromo-5-imidazol-1-yl-1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazole.
[0757] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 7.08 (m, 1H), 7.32 (m, 1H), 7.58 (m, 3H), 7.94 (m, 2H).
Preparation of 1-[5-bromo-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]-3-methylurea (IM7a, Process R)
[0758] ##STR00074##
[0759] Under argon, 3,5-dibromo-1-[4-(trifluoromethoxy)phenyl]-1H-1,2,4-triazole (IM-1a) (1000 mg, 2.58 mmol), N-methylurea (229 mg, 3.10 mmol), 4,5-bis-(diphenylphosphino)-9,9-dimethylxanthene (xantphos) (149 mg, 0.25 mmol) and tris-(dibenzylideneacetone)dipalladium (118 mg, 0.12 mmol) were initially charged in degassed dioxane (50 ml), and caesium carbonate (12630 mg, 3.87 mmol) was added. The mixture was then stirred at 80° C. for 3 h. The reaction mixture was filtered through kieselguhr, the filter cake was washed with ethyl acetate and the filtrate was concentrated under reduced pressure. The crude product was purified chromatographically on silica gel (gradient: cyclohexane/ethyl acetate). This gave 330 mg of 1-[5-bromo-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]-3-methylurea.
[0760] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 2.63 (d, 3H), 7.14 (m, 1H), 7.53 (m, 2H), 7.66 (m, 2H), 9.59 (s, 1H).
Preparation of N′-[5-bromo-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]-N,N-dimethylformamidine (IM-8a, Process T)
[0761] ##STR00075##
[0762] 3,5-Dibromo-1-[4-(trifluoromethoxy)phenyl]-1H-1,2,4-triazole (IM-1a) (150 mg, 0.46 mmol) and N,N-dimethylformamide dimethyl acetal (110 mg, 0.92 mmol) were initially charged in degassed toluene (50 ml), and the mixture was stirred at 40° C. for 4 h. The reaction mixture was concentrated under reduced pressure and the residue was purified chromatographically on silica gel (gradient: dichloromethane/ethyl acetate). This gave 92 mg of N′-[5-bromo-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]-N,N-dimethylformamidine.
[0763] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 3.04 (s, 3H), 3.18 (s, 3H), 7.49 (m, 2H), 8.04 (m, 2H), 8.56 (s, 1H).
Preparation of 4-[5-(methylamino)-1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]benzaldehyde (IM-9a, Process L)
[0764] ##STR00076##
[0765] A mixture of 5-bromo-N-methyl-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-amine (IM-2a) (980 mg, 2.90 mmol), 4-formylboronic acid pinacol ester (1012 mg, 4.36 mmol) and caesium carbonate (2.84 g, 8.72 mmol), dioxane (27 ml) and water (9 ml) was degassed under argon, and 1,1′-bis(diphenylphosphino)ferrocenepalladium(II) dichloride (142 mg, 0.17 mmol) was added. The mixture was then stirred at 90° C. for 3 h. The reaction mixture was filtered through kieselguhr, the filter cake was washed with ethyl acetate and the filtrate was concentrated under reduced pressure. The crude product was purified chromatographically on silica gel (gradient: cyclohexane/ethyl acetate). This gave 860 mg of 4-[5-(methylamino)-1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]benzaldehyde.
[0766] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 2.92 (s, 3H), 6.82 (m, 1H), 7.56 (m, 2H), 7.75 (m, 2H), 7.99 (m, 2H), 8.19 (m, 2H), 10.50 (s, 1H).
[0767] The following were obtained analogously to (IM-9a):
4-[5-(Cyclopropylamino)-1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]benzaldehyde (IM-9b)
[0768] ##STR00077##
[0769] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 0.53 (m, 2H), 0.65 (m, 2H), 2.62 (m, 1H), 6.82 (m, 1H), 7.54 (m, 2H), 7.74 (m, 2H), 8.00 (m, 2H), 8.19 (m, 2H), 10.50 (s, 1H).
[5-(Diethylamino)-1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]benzaldehyde (IM-9c)
[0770] ##STR00078##
[0771] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 0.97 (t, 6H), 3.11 (q, 4H), 7.56 (m, 2H), 7.75 (m, 2H), 7.99 (m, 2H), 8.19 (m, 2H), 10.51 (s, 1H).
[5-(Morpholino)-1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]benzaldehyde (IM-9d)
[0772] ##STR00079##
[0773] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 3.08 (m, 4H), 3.63 (m, 4H), 7.55 (m, 2H), 7.75 (m, 2H), 7.99 (m, 2H), 8.20 (m, 2H), 10.50 (s, 1H).
[5-(Ethylamino)-1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]benzaldehyde (IM-9e)
[0774] ##STR00080##
[0775] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 1.21 (t, 3H), 3.39 (m, 2H), 6.87 (m, 1H), 7.56 (m, 2H), 7.75 (m, 2H), 7.99 (m, 2H), 8.18 (m, 2H), 10.50 (s, 1H).
[5-(1-Methylethylamino)-1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]benzaldehyde (IM-9f)
[0776] ##STR00081##
[0777] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 1.17 (d, 6H), 3.86 (m, 1H), 6.87 (m, 1H), 7.56 (m, 2H), 7.74 (m, 2H), 7.98 (m, 2H), 8.18 (m, 2H), 10.50 (s, 1H).
[5-(Oxetanylamino)-1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]benzaldehyde (IM-9g)
[0778] ##STR00082##
[0779] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 4.62 (m, 2H), 4.80 (m, 2H), 4.92 (m, 1H), 7.60 (m, 3H), 7.80 (m, 2H), 7.99 (m, 2H), 8.16 (m, 2H), 10.50 (s, 1H).
4-[5-(2-Ethoxyethylamino)-1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]benzaldehyde (IM9h)
[0780] ##STR00083##
[0781] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 1.09 (t, 3H), 3.41-3.51 (m, 6H), 6.87 (m, 1H), 7.56 (m, 2H), 7.74 (m, 2H), 7.98 (m, 2H), 8.18 (m, 2H), 10.50 (s, 1H).
N′-[5-(4-Formylphenyl)-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]-N,N-dimethylformamidine (IM-9i)
[0782] ##STR00084##
[0783] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 3.04 (s, 3H), 3.18 (s, 3H), 6.87 (m, 1H), 7.56 (m, 2H), 7.74 (m, 2H), 7.98 (m, 2H), 8.18 (m, 2H), 10.50 (s, 1H).
4-[5-(Methylamino)-1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1,2,4-triazol-3-yl]benzaldehyde (IM-9j)
[0784] ##STR00085##
[0785] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 2.93 (s, 3H), 6.83 (m, 1H), 7.56 (m, 2H), 7.76 (m, 2H), 7.98 (m, 2H), 8.19 (m, 2H), 10.50 (s, 1H).
4-[5-(Tetrahydrofuran-3-yl-amino)-1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]benzaldehyde (IM-9k)
[0786] ##STR00086##
[0787] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 1.92 (m, 1H), 2.15 (m, 1H), 3.60 (m, 1H), 3.65 (m, 1H), 3.82 (m, 2H), 4.25 (m, 1H), 6.87 (m, 1H), 7.56 (m, 2H), 7.74 (m, 2H), 7.98 (m, 2H), 8.18 (m, 2H), 10.50 (s, 1H).
Preparation of 4-[5-amino-1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]benzaldehyde (IM10a, Process L)
[0788] ##STR00087##
[0789] A mixture of 5-bromo-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-amine (IM-3a) (500 mg, 1.54 mmol), 4-formylboronic acid pinacol ester (395 mg, 1.70 mmol) and sodium carbonate (459 mg, 4.33 mmol), ethanol (11 ml) and toluene (11 ml) was degassed under argon, and tetrakis(triphenylphosphine)palladium (89 mg, 0.07 mmol) was added. The mixture was then stirred at 90° C. for 16 h. The reaction mixture was diluted with ethyl acetate, 10% strength citric acid solution was added, the mixture was extracted repeatedly with ethyl acetate and the combined organic phases were washed with saturated sodium chloride solution. After drying over magnesium sulfate, the solvent was distilled off under reduced pressure and the crude product was purified chromatographically on silica gel (gradient: cyclohexane/ethyl acetate). This gave 229 mg of 4-[5-amino-1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]benzaldehyde.
[0790] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 6.79 (s, 2H), 7.55 (d, 2H), 7.70 (m, 2H), 7.99 (m, 2H), 8.12 (m, 2H), 10.09 (s, 1H).
[0791] The following were obtained analogously to (IM-10a):
4-[5-Amino-1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1,2,4-triazol-3-yl]benzaldehyde (IM-10b)
[0792] ##STR00088##
[0793] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 6.80 (s, 2H), 7.55 (d, 2H), 7.80 (m, 2H), 7.99 (m, 2H), 8.14 (m, 2H), 10.04 (s, 1H).
1-[4-[5-Amino-1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]ethanone (IM-10c)
[0794] ##STR00089##
[0795] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 2.33 (s, 3H), 6.82 (s, 2H), 7.68 (d, 2H), 7.94 (m, 2H), 8.12 (m, 2H), 8.19 (m, 2H),
Preparation of N-[5-(4-formylphenyl)-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]methanesulfonamide (IM-11a, Process L)
[0796] ##STR00090##
[0797] A mixture of N-[5-bromo-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]methanesulfonamide (IM5a) (130 mg, 0.32 mmol), 4-formylboronic acid pinacol ester (90 mg, 0.38 mmol) and potassium fluoride (49 mg, 0.84 mmol), acetonitrile (1.7 ml) and water (1.7 ml) was degassed under argon, and dichlorobis(triphenylphosphine)palladium (23 mg, 0.03 mmol) was added. The mixture was then heated in a microwave (Biotage) at 115° C. for 45 min. The reaction mixture was poured into water and filtered through a Chromabond™ PTS separation column. The crude product was purified chromatographically on silica gel (gradient: cyclohexane/ethyl acetate). This gave 100 mg of N-[5-(4-formylphenyl)-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]methanesulfonamide.
[0798] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 3.26 (s, 3H), 7.60 (d, 2H), 7.88 (m, 2H), 8.00 (m, 2H), 8.26 (m, 2H), 10.05 (s, 1H).
[0799] The following were obtained analogously to (IM-11a):
Preparation of N-[5-(4-formylphenyl)-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]ethanesulfonamide (IM-11b)
[0800] ##STR00091##
[0801] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 1.25 (t, 3H), 3.34 (q, 3H), 7.61 (d, 2H), 7.87 (m, 2H), 8.00 (m, 2H), 8.26 (m, 2H), 10.05 (s, 1H).
Preparation of 1,1-difluoro-N-[5-(4-formylphenyl)-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]methanesulfonamide (IM-11c)
[0802] ##STR00092##
[0803] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 6.73 (t, 1H), 7.54 (d, 2H), 8.01 (m, 2H), 8.15 (m, 2H), 8.25 (m, 2H), 10.06 (s, 1H).
Preparation of N-[5-(4-formylphenyl)-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]cyclopropanesulfonamide (IM-11d)
[0804] ##STR00093##
[0805] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 0.53 (m, 2H), 0.63 (m, 2H), 3.46 (m, 1H), 7.60 (d, 2H), 7.88 (m, 2H), 8.00 (m, 2H), 8.26 (m, 2H), 10.06 (s, 1H).
Preparation of N-[5-(4-formylphenyl)-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]acetamide (Process N-1, IM-12a)
[0806] ##STR00094##
[0807] 4-[5-Amino-1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]benzaldehyde (IM-10a) (360 mg, 1.03 mmol) was initially charged in dichloroethane (7 ml), and first pyridine (180 mg, 2.27 mmol) and then, with ice cooling, acetyl chloride (178 mg, 2.27 mmol) were added. The mixture was then stirred at 60° C. for 5 h. The reaction mixture was diluted with dichloromethane, water was added and the mixture was filtered through a Chromabond™ PTS separation column. The crude product was purified chromatographically on silica gel (gradient: cyclohexane/ethyl acetate). This gave 90 mg of N-[5-(4-formylphenyl)-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]acetamide.
[0808] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 2.05 (s, 3H), 7.57 (m, 2H), 7.77 (m, 2H), 8.04 (m, 2H), 8.24 (m, 2H), 10.09 (s, 1H), 10.85 (s, 1H).
[0809] The following was obtained analogously to (IM-12a):
N-[5-(4-Formylphenyl)-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]acetamide (IM-12b)
[0810] ##STR00095##
[0811] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 0.98 (t, 3H), 2.34 (m, 2H), 7.57 (m, 2H), 7.77 (m, 2H), 8.04 (m, 2H), 8.24 (m, 2H), 10.07 (s, 1H), 10.83 (s, 1H).
Preparation of 5-(4-aminophenyl)-N-methyl-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazole-3-amine (IM-13a, Process M)
[0812] ##STR00096##
[0813] A mixture of 5-bromo-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-amine (IM-2a) (235 mg, 0.69 mmol), 4-formylboronic acid pinacol ester (183 mg, 0.83 mmol) and potassium fluoride (105 mg, 1.81 mmol), acetonitrile (2.5 ml) and water (2.5 ml) was degassed under argon, and dichlorobis(triphenylphosphine)palladium (51 mg, 0.07 mmol) was added. The mixture was then heated in a microwave (Biotage) at 115° C. for 45 min. The reaction mixture was poured into water and filtered through a Chromabond™ PTS separation column. The crude product was purified chromatographically on silica gel (gradient: cyclohexane/ethyl acetate). This gave 144 mg of 5-(4-aminophenyl)-N-methyl-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-amine.
[0814] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 2.89 (d, 3H), 5.35 (s, 2H), 6.57 (m, 2H), 6.86 (s, 1H), 7.63 (m, 4H), 8.00 (m, 2H).
[0815] The following were prepared analogously to (IM-13a):
5-(4-Aminophenyl)-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-amine (IM-13b)
[0816] ##STR00097##
[0817] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 5.34 (s, 2H), 6.52 (s, 2H), 6.57 (m, 2H), 7.50 (m, 2H), 7.62 (m, 2H), 7.71 (m, 2H).
5-(4-Aminophenyl)-N-cyclobutyl-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-amine (IM-13c)
[0818] ##STR00098##
[0819] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 1.64 (m, 2H), 2.04 (m, 2H), 2.18 (m, 2H), 4.13 (m, 1H), 5.73 (s, 2H), 6.58 (m, 2H), 6.84 (m, 1H), 7.51 (m, 2H), 7.63 (m, 2H), 7.68 (m, 2H).
5-(4-Aminophenyl)-N-ethyl-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-amine (IM-13d)
[0820] ##STR00099##
[0821] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 0.99 (t, 3H), 3.13 (q, 2H), 5.75 (s, 2H), 6.59 (m, 2H), 6.82 (m, 1H), 7.51 (m, 2H), 7.63 (m, 2H), 7.68 (m, 2H).
5-(4-Aminophenyl)-N-(2-ethoxyethyl)-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-amine (IM13e)
[0822] ##STR00100##
[0823] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 1.09 (t, 3H), 3.41-3.51 (m, 6H), 5.76 (s, 2H), 6.59 (m, 2H), 6.84 (m, 1H), 7.53 (m, 2H), 7.63 (m, 2H), 7.67 (m, 2H).
5-(4-Aminophenyl)-N-(1-methyethyl)-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-amine (IM13f)
[0824] ##STR00101##
[0825] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 1.16 (d, 6H), 3.85 (m, 1H), 5.75 (s, 2H), 6.58 (s, 2H), 6.84 (m, 1H), 7.51 (m, 2H), 7.63 (m, 2H), 7.68 (m, 2H).
5-(4-Aminophenyl)-N-(oxetan-3-yl)-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-amine (IM-13g)
[0826] ##STR00102##
[0827] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 4.56 (m, 2H), 4.75 (m, 2H), 4.90 (m, 1H), 5.35 (s, 2H), 6.58 (m, 2H), 6.82 (m, 1H), 7.54 (m, 2H), 7.65 (m, 2H), 7.73 (m, 2H).
5-(4-Aminophenyl)-N-(tetrahydrofuran-3-yl)-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-amine (IM-13h)
[0828] ##STR00103##
[0829] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 1.92 (m, 1H), 2.15 (m, 1H), 3.60 (m, 1H), 3.65 (m, 1H), 3.82 (m, 2H), 4.25 (m, 1H), 5.35 (s, 2H), 6.58 (m, 2H), 6.82 (m, 1H), 7.54 (m, 2H), 7.65 (m, 2H), 7.73 (m, 2H).
5-(4-Aminophenyl)-N-methoxy-N-methyl-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-amine (IM-13i)
[0830] ##STR00104##
[0831] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 3.08 (s, 3H), 3.12 (s, 3H), 5.37 (s, 2H), 6.57 (m, 2H), 7.54 (m, 2H), 7.66 (m, 2H), 7.74 (m, 2H).
5-(4-Aminophenyl)-N-methyl-2-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1,2,4-triazol-3-amine (IM13j)
[0832] ##STR00105##
[0833] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 2.88 (d, 3H), 5.35 (m, 1H), 6.60 (m, 2H), 7.52 (m, 2H), 7.64-7.78 (m, 4H).
[5-(4-Aminophenyl)-2-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1,2,4-triazol-3-yl]cyanamide (IM13k)
[0834] ##STR00106##
[0835] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 5.75 (m, 1H), 6.63 (m, 2H), 7.52 (m, 2H), 7.72 (m, 4H), 8.06 (m, 2H).
5-(4-Aminophenyl)-2-[4-(1,1,2,2,2-pentafluorethoxy)phenyl]-1,2,4-triazol-3-amine (IM-131)
[0836] ##STR00107##
[0837] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 5.34 (s, 2H), 6.52 (s, 2H), 6.58 (m, 2H), 7.51 (m, 2H), 7.62 (m, 2H), 7.73 (m, 2H).
Preparation of (5-chloro-3-(4-nitrophenyl)-1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazole (Process V, IM-14a)
[0838] ##STR00108##
Step 1:
[0839] Conc. HCl (1 ml) was added to a solution of 2-(4-nitrophenyl)-2-oxoacetic acid (3.51 g, 18 mmol) and (4-trifluormethoxy)phenylhydrazine (3.42 g, 15 mmol) in water (250 ml). The mixture was then stirred at room temperature for 4 h. The precipitated crude product was filtered off and washed with water (3×20 ml). Drying gave 3.32 g of 2-(4-nitrophenyl)-2-[[4-(trifluoromethoxy)phenyl]hydrazono]acetic acid.
[0840] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 7.2-7.5 (m, 4H), 7.98 (m, 2H), 8.24 (m, 2H), 10.08 (s, 1H), 12.6 (br.s, 1H).
Step 2:
[0841] Triethylamine (909 mg, 9 mmol) was added to a solution of 2-(4-nitrophenyl)-2-[[4-(trifluoromethoxy)phenyl]hydrazono]acetic acid (3.32 g, 9 mmol) from Step 1 and diphenylphosphoryl azide (DPPA) (2.47 g, 9 mmol) in toluene (100 ml). The mixture was then heated under reflux for 1 h. After cooling, the reaction mixture was extracted with 100 ml of NaOH (1N), and the extract was neutralized with conc. HCl. The precipitated product was filtered off, washed with water and dried. This gave 2.96 g of 5-(4-nitrophenyl)-2-[4-(trifluoromethoxy)phenyl]-4H-1,2,4-triazol-3-one.
[0842] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 7.53 (d, 2H), 8.14 (m, 4H), 8.42 (d, 2H), 10.08 (s, 1H), 13.07 (s, 1H).
Step 3:
[0843] A solution of 5-(4-nitrophenyl)-2-[4-(trifluoromethoxy)phenyl]-4H-1,2,4-triazol-3-one (2.96 g, 8 mmol) from Step 2 in phosphoryl chloride (30 ml) was heated under reflux for 24 h. After cooling, the reaction mixture was poured into water, neutralized with sodium bicarbonate and extracted with ethyl acetate. The organic phase was washed with water and dried over magnesium sulfate. Distillative removal of the solvent under reduced pressure gave 2.8 g of (5-chloro-3-(4-nitrophenyl)-1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazole.
[0844] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 7.67 (d, 2H), 7.93 (d, 2H), 8.28 (d, 2H), 8.38 (d, 2H).
[0845] The following were prepared analogously to (IM-14a):
(5-Chloro-3-(4-nitrophenyl)-1-[4-(1,1,2,2,2pentafluorethoxy)phenyl]-1,2,4-triazole (IM-14b)
[0846] ##STR00109##
[0847] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 7.69 (d, 2H), 7.94 (d, 2H), 8.28 (d, 2H), 8.39 (d, 2H).
Preparation of N-[5-(4-aminophenyl)-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]acetamide (Process I, IM-15a)
[0848] ##STR00110##
Step 1:
[0849] First (5-chloro-3-(4-nitrophenyl)-1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazole (IM-14a) (567 mg, 1.5 mmol) and then acetamide (133 g, 2.25 mmol) were added to a suspension of sodium hydride (120 mg, 3 mmol) in dimethylformamide (10 ml). The reaction mixture was stirred at 80° C. for 2 h, cooled and diluted with saturated sodium chloride solution (100 ml). After repeated extraction with ethyl acetate, the organic phase was dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (gradient: cyclohexane/ethyl acetate), which gave 305 mg of N-[5-(4-nitrophenyl)-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]acetamide.
[0850] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 2.05 (s, 3H), 7.57 (d, 2H), 7.80 (d, 2H), 8.26 (d, 2H), 8.37 (d, 2H), 10.92 (s, 1H).
Step 2:
[0851] First copper chloride (74 mg, 0.75 mmol) and then sodium borohydride (285 mg, 7.5 mmol) were added to a solution of N-[5-(4-nitrophenyl)-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]acetamide (Step 1) (305 mg, 0.75 mmol) in methanol (10 ml). The reaction mixture was stirred at room temperature for 0.5 h and concentrated under reduced pressure. Subsequently, saturated sodium chloride solution was added and the mixture was extracted with ethyl acetate. The organic phase was dried over sodium sulfate and the solvent was distilled off under reduced pressure. The crude product was purified by chromatography on silica gel (gradient: cyclohexane/ethyl acetate), which gave 260 mg of N-[5-(4-aminophenyl)-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]acetamide.
[0852] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 2.02 (s, 3H), 5.48 (s, 2H), 6.60 (d, 2H), 7.51 (d, 2H), 7.69 (m, 4H), 10.69 (s, 1H).
[0853] The following were prepared analogously to (IM-15a):
N-[5-(4-Aminophenyl)-2-[4-(trifluoroethoxy)phenyl]-1,2,4-triazol-3-yl]acetamide (IM-15b)
[0854] ##STR00111##
[0855] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 0.99 (t, 3H), 3.13 (q, 2H), 5.48 (s, 2H), 6.60 (d, 2H), 7.51 (d, 2H), 7.69 (m, 4H), 10.69 (s, 1H).
N-[5-(4-Aminophenyl)-2-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1,2,4-triazol-3-yl]acetamide (IM15c)
[0856] ##STR00112##
[0857] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 2.03 (s, 3H), 5.48 (s, 2H), 6.62 (d, 2H), 7.51 (d, 2H), 7.68 (m, 4H), 10.69 (s, 1H).
N-[5-(4-Aminophenyl)-2-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1,2,4-triazol-3-yl]propanamide (IM-15d)
[0858] ##STR00113##
[0859] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 0.99 (t, 3H), 3.13 (q, 2H), 5.48 (s, 2H), 6.61 (d, 2H), 7.51 (d, 2H), 7.70 (m, 4H), 10.68 (s, 1H).
N-[5-(4-Aminophenyl)-2-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1,2,4-triazol-3-yl]cyclopropanecarboxamide (IM-15e)
[0860] ##STR00114##
[0861] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 0.52 (m, 2H), 0.64 (m, 2H), 2.33 (m, 1H), 5.48 (s, 2H), 6.62 (d, 2H), 7.51 (d, 2H), 7.69 (m, 4H), 10.70 (s, 1H).
Preparation of N-{3-(4-formylphenyl)-1-[4-(trifluoromethoxy)phenyl]-1H-pyrazol-5-yl}acetamide (Process P, IM-16)
[0862] ##STR00115##
Step 1:
[0863] A mixture of methyl 4-(cyanacetyl)benzoate (1.00 g, 4.92 mmol), [4-(trifluoromethoxy)phenyl]hydrazine hydrochloride (1.24 g, 5.41 mmol) and methanol (20 ml) was stirred under reflux for 4 h. After cooling to room temperature, the precipitated solid was filtered off. The filter residue was washed with petroleum ether and dried under reduced pressure. This gave 486 mg (purity 63%) of methyl 4-[5-amino-1-[4-(trifluoromethoxy)phenyl]-1H-pyrazol-3-yl]benzoate. The filtrate was concentrated under reduced pressure, adsorbed on silica gel and separated chromatographically by MPLC on silica gel (gradient: cyclohexane/ethyl acetate). This gave a further 865 mg of methyl 4-{5-amino-1-[4-(trifluoromethoxy)phenyl]-1H-pyrazol-3-yl}benzoate.
[0864] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 3.86 (s, 3H), 5.65 (s, 2H), 6.03 (s, 1H), 7.52 (d, 2H), 7.82 (d, 2H), 7.91 (d, 2H), 7.98 (d, 2H).
Step 2:
[0865] A mixture of methyl 4-{5-amino-1-[4-(trifluoromethoxy)phenyl]-1H-pyrazol-3-yl}benzoate (827 mg, 2.19 mmol) and acetic anhydride (3.5 ml) was stirred at room temperature for 23 h. After concentration of the reaction mixture under reduced pressure, the residue was adsorbed on silica gel and separated chromatographically by MPLC on silica gel (gradient: cyclohexane/ethyl acetate). This gave 672 mg of methyl 4-{5-acetamido-1-[4-(trifluoromethoxy)phenyl]-1H-pyrazol-3-yl}benzoate.
[0866] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 2.03 (s, 3H), 3.87 (s, 3H), 7.03 (s, 1H), 7.56 (d, 2H), 7.74 (d, 2H), 8.02 (s, 4H), 10.16 (s, 1H).
Step 3:
[0867] Under argon, a solution of methyl 4-{5-acetamido-1-[4-(trifluoromethoxy)phenyl]-1H-pyrazol-3-yl}benzoate (448 mg, 1.07 mmol) in tetrahydrofuran (6 ml) was added to a mixture of lithium borohydride (35 mg, 1.60 mmol) in tetrahydrofuran (5 ml), and the mixture was stirred at room temperature for 90 h. After addition of water, the mixture was extracted repeatedly with dichloromethane and the combined organic phases were concentrated under reduced pressure. The mixture was then adsorbed on RP-18 silica gel and separated chromatographically by MPLC on RP-18 silica gel (gradient: water/acetonitrile). This gave 99 mg of N-{3-[4-(hydroxymethyl)phenyl]-1-[4-(trifluoromethoxy)phenyl]-1H-pyrazol-5-yl}acetamide.
[0868] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 2.02 (s, 3H), 4.53 (d, 2H), 5.22 (t, 1H), 6.88 (s, 1H), 7.38 (d, 2H), 7.54 (d, 2H), 7.72 (d, 2H), 7.81 (d, 2H), 10.09 (s, 1H).
Step 4:
[0869] Manganese dioxide (111 mg, 1.28 mmol) was added to a solution of N-{3-[4-(hydroxymethyl)phenyl]-1-[4-(trifluoromethoxy)phenyl]-1H-pyrazol-5-yl}acetamide (50 mg, 128 μmol) in chloroform (2 ml), and the mixture was stirred at 40° C. for 3 h and at room temperature for a further 16 h. After concentration of the reaction mixture under reduced pressure, the residue was adsorbed on silica gel and separated chromatographically by MPLC on silica gel (gradient: cyclohexane/ethyl acetate). This gave 20 mg of N-{3-(4-formylphenyl)-1-[4-(trifluoromethoxy)phenyl]-1H-pyrazol-5-yl}acetamide.
[0870] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): δ 2.03 (s, 3H), 7.07 (s, 1H), 7.57 (d, 2H), 7.74 (d, 2H), 7.98 (d, 2H), 8.10 (d, 2H), 10.03 (s, 1H), 10.17 (s, 1H).
Preparation of 1-(2-isopropylphenyl)-3-[[4-[5-(methylamino)-1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]methyleneamino]thiourea (I-018, Process A)
[0871] ##STR00116##
[0872] A mixture of 4-[5-(methylamino)-1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]benzaldehyde (IM12a) (860 mg, 2.37 mmol) and N-(2-isopropylphenyl)hydrazinecarbothioamide (496 mg, 2.37 mmol) (known from WO 2010/062559) in ethanol (30 ml) was stirred at room temperature for 16 h. The solvent was distilled off under reduced pressure and the residue was chromatographed on silica gel (gradient: cyclohexane/ethyl acetate). This gave 790 mg of 1-(2-isopropylphenyl)-3-[[4-[5-(methylamino)-1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]methyleneamino]thiourea.
[0873] .sup.1H NMR see Table 1
Preparation of 3-(2-isopropylphenyl)-2-[[4-[5-(methylamino)-1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]methylenehydrazono]thiazolidin-4-one (I-24, Process C)
[0874] ##STR00117##
[0875] 1-(2-Isopropylphenyl)-3-[[4-[5-(methylamino)-1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]methyleneamino]thiourea (I-018) (80 mg, 0.140 mmol) was initially charged in ethanol (5 ml), sodium acetate (47.4 mg, 0.570 mmol) was added, methyl bromoacetate (26.5 mg, 0.170 mmol) was added and the mixture was then stirred at 60° C. for 16 h. The reaction mixture was poured onto water and the precipitated solid was filtered off. The crude product was chromatographed on silica gel (gradient: cyclohexane/ethyl acetate). This gave 50 mg of 3-(2-isopropylphenyl)-2-[[4-[5-(methylamino)-1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]methylenehydrazono]thiazolidin-4-one.
[0876] .sup.1H NMR see Table 1
Preparation of 3-[4-({[3-(2-isopropylphenyl)-4-methyl-1,3-thiazol-2(3H)-ylidene]hydrazono}methyl)phenyl]-N-methyl-1-[4-(trifluoromethoxy)phenyl]-1H-1,2,4-triazol-5-amine (I-097, Process C)
[0877] ##STR00118##
[0878] A mixture of N-(2-isopropylphenyl)-2-(4-{5-(methylamino)-1-[4-(trifluoromethoxy)phenyl]-1H-1,2,4-triazol-3-yl}benzylidene)hydrazinecarbothioamide (250 mg, 452 μmol), 1-chloroacetone (51 μl, 632 μmol), sodium acetate (148 mg, 1.81 mmol) and ethanol (5 ml) was stirred at 70° C. for 4 h. After concentration of the reaction mixture under reduced pressure, the residue was dissolved in acetonitrile and, after removal of the insoluble residue by filtration, separated chromatographically by preparative HPLC on RP-18 (gradient: water/acetonitrile+0.01% formic acid). This gave 160 mg of 3-[4-({[3-(2-isopropylphenyl)-4-methyl-1,3-thiazol-2(3H)-ylidene]hydrazono}methyl)phenyl]-N-methyl-1-[4-(trifluoromethoxy)phenyl]-1H-1,2,4-triazol-5-amine as a diastereomer mixture.
[0879] .sup.1H NMR see Table 1.
Preparation of 3-{4-[({2-[(2-isopropylphenyl)imino]-1,3-thiazinan-3-yl}imino)methyl]phenyl}-N-methyl-1-[4-(pentafluoroethoxy)phenyl]-1H-1,2,4-triazol-5-amine (I-125) and 3-[4-({[3-(2-isopropylphenyl)-1,3-thiazinan-2-yliden]hydrazono}methyl)phenyl]-N-methyl-1-[4-(pentafluoroethoxy)phenyl]-1H-1,2,4-triazol-5-amine (I-126, Process C)
[0880] ##STR00119##
[0881] A mixture of N-(2-isopropylphenyl)-2-(4-{5-(methylamino)-1-[4-(pentafluoroethoxy)phenyl]-1H-1,2,4-triazol-3-yl}benzylidene)hydrazinecarbothioamide (100 mg, 166 μmol), 1,3-dibromopropane (84 mg, 414 μmol), potassium carbonate (92 mg, 663 μmol) and butan-2-one (5 ml) was stirred at 90° C. for 6 h and then at room temperature overnight. After concentration of the reaction mixture under reduced pressure, the residue was separated chromatographically by preparative HPLC on RP-18 (gradient: water/acetonitrile+0.01% formic acid). This gave 60 mg of 3-{4-[({2-[(2-isopropylphenyl)imino]-1,3-thiazinan-3-yl}imino)methyl]phenyl}-N-methyl-1-[4-(pentafluoroethoxy)phenyl]-1H-1,2,4-triazol-5-amine (I-125) and 23 mg of 3-[4-({[3-(2-isopropylphenyl)-1,3-thiazinan-2-yliden]hydrazono}methyl)phenyl]-N-methyl-1-[4-(pentafluoroethoxy)phenyl]-1H-1,2,4-triazol-5-amine (I-126).
[0882] .sup.1H NMR see Table 1.
Preparation of 1-[3-(2-isopropylphenyl)-4-oxo-thiazolidin-2-ylidene]-3-[4-[5-(methylamino)-1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]urea (I-026, Process G)
[0883] ##STR00120##
Step 1:
[0884] 5-(4-Aminophenyl)-N-methyl-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-amine (IM-13a) (86 mg, 0.220 mmol) was initially charged in THF (2.5 ml), and a solution of 4-nitrophenyl chloroformate (49 mg, 0.24 mmol) in THF (2.5 ml) was added. After 16 h of stirring at room temperature, hexane (5 ml) was added and the precipitated solid was filtered off with suction, giving 150 mg of (4-nitrophenyl)N-[4-[5-(methylamino)-1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamate hydrochloride which was reacted further in step 2 without purification.
Step 2:
[0885] 2-Imino-3-(2-isopropylphenyl)thiazolidin-4-one (63.8 mg, 0.27 mmol) (known from WO2016/033025) was initially charged in 5 ml of acetonitrile, and first caesium carbonate (133 mg, 0.40 mmol) and then (4-nitrophenyl)-N-[4-[5-(methylamino)-1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamate hydrochloride from step 1 (150 mg, 0.27 mmol) were added. After 1 h of stirring at 70° C., the reaction mixture was poured onto water and extracted repeatedly with dichloromethane, and the organic phase was, after drying over magnesium sulfate, concentrated under reduced pressure. The residue was chromatographed on silica gel (gradient: cyclohexane/ethyl acetate). This gave 27 mg of 1-[3-(2-isopropylphenyl)-4-oxothiazolidin-2-ylidene]-3-[4-[5-(methylamino)-1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]urea.
[0886] .sup.1H NMR see Table 1
Preparation of 1-[4-[5-amino-1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]-3-[3-(2-isopropylphenyl)-4-oxo-thiazolidin-2-ylidene]urea (I-025, Process G)
[0887] ##STR00121##
Step 1:
[0888] 5-(4-Aminophenyl)-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-amine (IM-13b) (120 mg, 0.35 mmol) was initially charged in THF (2.55 ml), and a solution of 4-nitrophenyl chloroformate (79 mg, 0.39 mmol) in THF (2.5 ml) was added. After 16 h of stirring at room temperature, hexane (5 ml) was added and the precipitated solid was filtered off with suction, giving 180 mg of (4-nitrophenyl) [4-(5-amino)-1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamate hydrochloride which was reacted further in step 2 without purification.
Step 2:
[0889] 2-Imino-3-(2-isopropylphenyl)thiazolidin-4-one (78.5 mg, 0.33 mmol) (known from WO2016/033025) was initially charged in 5 ml of acetonitrile, and first caesium carbonate (163 mg, 0.50 mmol) and then (4-nitrophenyl)-N-[4-[5-(amino)-1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamate hydrochloride from step 1 (180 mg, 0.33 mmol) were added. After 1 h of stirring at 70° C., the reaction mixture was poured onto water and extracted repeatedly with dichloromethane, and the organic phase was, after drying over magnesium sulfate, concentrated under reduced pressure. The residue was chromatographed on silica gel (gradient: cyclohexane/ethyl acetate). This gave 27 mg of 1-[4-[5-amino-1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]-3-[3-(2-isopropylphenyl)-4-oxothiazolidin-2-ylidene]urea.
[0890] .sup.1H NMR see Table 1
Preparation of N-[5-[4-[[3-(2-isopropylphenyl)-4-oxothiazolidin-2-ylidene]carbamoylamino]phenyl]-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]cyclopropanecarboxamide (I-029, Process H)
[0891] ##STR00122##
[0892] 1-[4-[5-Amino-1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]-3-[3-(2-isopropylphenyl)-4- oxothiazolidin-2-ylidene]urea (I-025) (100 mg, 0.16 mmol) was initially charged in chloroform (2.5 ml), and first pyridine (26.5 mg, 0.33 mmol) and then cyclopropylcarbonyl chloride (21.7 mg, 0.20 mmol) were added. The reaction mixture was stirred at room temperature for 18 h, diluted with dichloromethane, and 1M hydrochloric acid (7.5 ml) was added. After filtration through a Chromabond™ PTS separating column, the organic phase was concentrated and the residue was chromatographed on silica gel (gradient: cyclohexane/ethyl acetate). This gave 54 mg of N-[5-[4-[[3-(2-isopropylphenyl)-4-oxothiazolidin-2-ylidene]carbamoylamino]phenyl]-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]cyclopropanecarboxamide.
[0893] .sup.1H NMR see Table 1
Preparation of [(2S,3R,4R,5S,6S)-4-ethoxy-3,5-dimethoxy-6-methyl-tetrahydropyran-2-yl]N-[4-[5-acetamido-1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamate (I-001, Process E)
[0894] ##STR00123##
Step 1:
[0895] Triphosgene (120 mg, 0.4 mmol) was added to a solution of N-[5-(4-aminophenyl)-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]acetamide (IM-15a) (150 mg, 0.40 mmol) in ethyl acetate (10 ml), and the mixture was stirred at 70° C. for 1 h. The reaction mixture was concentrated under reduced pressure, giving 170 mg of N-[5-(4-isocyanatophenyl)-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]acetamide which was immediately reacted further without purification.
Step 2:
[0896] At room temperature, (2R,3R,4R,5S,6S)-4-ethoxy-3,5-dimethoxy-6-methyltetrahydropyran-2-ol (known from US 2010/0204165) (44 mg, 0.20 mmol) was added to a mixture of N-[5-(4-isocyanatophenyl)-2-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]acetamide (step 1) (85 mg, 0.20 mmol) and caesium carbonate (72 mg, 0.22 mmol) in acetonitrile (5 ml). After 2 h of stirring, the mixture was filtered, the filtrate was concentrated under reduced pressure and the residue was purified chromatographically on silica gel (gradient: cyclohexane/ethyl acetate). This gave 36 mg of [(2S,3R,4R,5S,6S)-4-ethoxy-3,5-dimethoxy-6-methyl-tetrahydropyran-2-yl]N-[4-[5-acetamido-1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamate.
[0897] .sup.1H NMR see Table 1
[0898] The NMR data of selected examples are listed either in conventional form (6 values, multiplet splitting, number of hydrogen atoms) or as NMR peak lists.
[0899] In each case, the solvent in which the NMR spectrum was recorded is stated.
[0900] In analogy to the examples and according to the above-described preparation processes, the compounds of the formula (I) specified in table 1 can be obtained
##STR00124##
TABLE-US-00001 TABLE 1 Ex. no. Structure NMR data I-001 [00125]
I-001: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 10.7633 (0.5); 10.0289 (2.5); 7.9659 (5.7); 7.9441 (6.6); 7.8605 (0.3); 7.7478 (5.9); 7.7429 (2.3); 7.7307 (3.0); 7.7254 (7.3); 7.6147 (3.3); 7.5937 (3.0); 7.5666 (5.0); 7.5451 (4.3); 7.5225 (0.3); 6.6432 (0.3); 5.9439 (4.2); 5.9392 (4.2); 3.7301 (0.5); 3.7126 (1.8); 3.7052 (2.7); 3.6965 (4.3); 3.6912 (3.8); 3.6721 (2.0); 3.6542 (1.1); 3.6493 (1.1); 3.6194 (2.3); 3.6110 (2.4); 3.5961 (2.0); 3.5891 (1.7); 3.5663 (0.6); 3.5488 (1.8); 3.5312 (2.0); 3.5258 (1.7); 3.5082 (1.6); 3.4903 (0.8); 3.4687 (21.4); 3.4346 (25.9); 3.3174 (67.0); 3.0808 (2.0); 3.0575 (3.5); 3.0341 (1.6); 2.6741 (0.5); 2.6699 (0.6); 2.6656 (0.4); 2.5053 (76.6); 2.5010 (97.6); 2.4967 (70.0); 2.3322 (0.4); 2.3279 (0.6); 2.3234 (0.4); 2.0739 (2.0); 2.0334 (16.0); 1.1998 (7.0); 1.1891 (11.6); 1.1825 (14.9); 1.1739 (10.9); 1.1652 (6.7); 0.0076 (3.0); −0.0003 (46.6) I-002 [00126]
I-002: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 11.0476 (2.6); 10.0214 (2.9); 7.9698 (6.2); 7.9481 (7.5); 7.7190 (6.1); 7.6966 (8.4); 7.6145 (3.7); 7.5935 (3.5); 7.5728 (6.8); 7.5506 (5.2); 6.5099 (0.6); 5.9436 (4.6); 5.9391 (4.6); 4.0379 (0.5); 4.0201 (0.5); 3.7300 (0.5); 3.7126 (1.8); 3.7037 (2.7); 3.6957 (5.1); 3.6899 (4.5); 3.6719 (2.2); 3.6500 (1.2); 3.6195 (2.5); 3.6113 (2.6); 3.5963 (2.1); 3.5891 (1.8); 3.5672 (0.7); 3.5499 (2.0); 3.5325 (2.3); 3.5269 (1.8); 3.5092 (1.7); 3.4916 (0.8); 3.4686 (23.3); 3.4349 (28.9); 3.3101 (255.5); 3.0811 (2.2); 3.0579 (4.0); 3.0346 (1.8); 2.6692 (1.5); 2.5044 (194.5); 2.5002 (255.4); 2.4960 (186.9); 2.3271 (1.6); 1.9877 (2.2); 1.8484 (0.5); 1.8379 (1.0); 1.8294 (1.2); 1.8187 (1.9); 1.8075 (1.3); 1.7993 (1.0); 1.7875 (0.5); 1.3978 (1.0); 1.2378 (0.6); 1.1999 (7.6); 1.1893 (12.6); 1.1826 (16.0); 1.1741 (12.9); 1.1652 (7.3); 1.1567 (1.2); 1.0725 (0.4); 1.0551 (0.8); 1.0376 (0.4); 0.8552 (0.6); 0.8316 (2.8); 0.8232 (3.7); 0.8128 (3.0); 0.8040 (3.0); 0.6837 (1.5); 0.6754 (3.6); 0.6660 (4.4); 0.6576 (3.2); 0.6477 (1.0); 0.1458 (0.5); 0.0076 (5.4); −0.0003 (121.2); −0.0085 (4.5); −0.1496 (0.5) I-003 [00127]
I-003: .sup.1H-NMR(300.1 MHz, d.sub.6-DMSO): δ = 10.7336 (3.8); 10.0401 (3.4); 9.8545 (0.5); 7.9757 (6.1); 7.9465 (7.6); 7.9114 (0.8); 7.7571 (0.7); 7.7461 (6.3); 7.7232 (2.7); 7.7160 (9.0); 7.6224 (4.3); 7.5937 (4.0); 7.5724 (7.1); 7.5425 (5.1); 6.5197 (0.4); 5.9746 (4.4); 5.9678 (4.4); 4.1627 (0.8); 4.1391 (0.8); 3.7689 (2.3); 3.7599 (3.4); 3.7513 (2.3); 3.6813 (0.5); 3.6621 (1.2); 3.6400 (1.2); 3.6305 (1.4); 3.6096 (1.2); 3.5900 (0.4); 3.5334 (1.8); 3.5229 (1.6); 3.5023 (2.0); 3.4923 (2.0); 3.4485 (23.7); 3.4300 (29.7); 3.3979 (28.4); 3.3576 (0.4); 3.3165 (133.2); 3.0926 (2.1); 3.0617 (3.8); 3.0305 (1.7); 2.7324 (0.8); 2.7270 (0.9); 2.7209 (0.7); 2.5401 (1.0); 2.5126 (56.4); 2.5068 (110.3); 2.5009 (144.9); 2.4950 (99.4); 2.3629 (1.5); 2.3379 (5.1); 2.3129 (5.3); 2.2875 (1.8); 2.2771 (0.8); 2.2706 (1.0); 2.2647 (0.6); 2.0738 (0.6); 1.2853 (0.9); 1.2613 (1.9); 1.2378 (1.2); 1.1968 (10.5); 1.1762 (10.3); 1.0039 (7.5); 0.9788 (16.0); 0.9537 (7.0); 0.1950 (0.4); 0.0107 (3.5); −0.0002 (91.2); −0.0112 (2.9); −0.1993 (0.4) I-004 [00128]
I-004: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 10.0341 (4.1); 7.9719 (8.9); 7.9502 (10.6); 7.7202 (8.6); 7.6978 (11.8); 7.6188 (5.4); 7.5976 (5.1); 7.5731 (9.5); 7.5509 (7.3); 5.9733 (6.6); 5.9685 (6.6); 3.7647 (3.4); 3.7581 (5.1); 3.7520 (3.5); 3.6697 (0.5); 3.6551 (1.5); 3.6398 (1.8); 3.6323 (1.8); 3.6167 (1.6); 3.6045 (0.7); 3.5725 (0.4); 3.5281 (2.4); 3.5208 (2.3); 3.5051 (2.7); 3.4977 (2.6); 3.4486 (34.8); 3.4302 (42.5); 3.3983 (41.1); 3.3579 (1.5); 3.3142 (7.7); 3.2699 (0.6); 3.2631 (0.8); 3.2509 (0.5); 3.2199 (0.4); 3.0859 (3.2); 3.0626 (5.8); 3.0393 (2.6); 2.6695 (0.8); 2.5047 (104.0); 2.5004 (136.5); 2.4962 (99.4); 2.3317 (0.6); 2.3274 (0.8); 2.0728 (0.8); 1.8511 (0.6); 1.8398 (1.3); 1.8308 (1.7); 1.8203 (2.6); 1.8094 (1.8); 1.8010 (1.4); 1.7893 (0.7); 1.2351 (0.4); 1.1943 (16.0); 1.1789 (15.8); 1.1392 (0.4); 1.1237 (0.4); 0.8415 (1.4); 0.8316 (3.7); 0.8236 (5.1); 0.8130 (4.1); 0.8043 (4.2); 0.7964 (1.7); 0.6844 (2.0); 0.6760 (5.0); 0.6665 (6.2); 0.6582 (4.5); 0.6486 (1.4); 0.1459 (0.3); 0.0076 (3.1); −0.0003 (73.5); −0.0084 (2.7) I-005 [00129]
I-005: .sup.1H-NMR(300.1 MHz, d.sub.6-DMSO): δ = 10.7329 (3.5); 10.0287 (3.4); 7.9744 (6.3); 7.9453 (7.8); 7.7574 (0.7); 7.7465 (6.4); 7.7395 (2.3); 7.7238 (2.7); 7.7165 (9.1); 7.7060 (1.0); 7.6194 (4.3); 7.5906 (4.0); 7.5719 (6.8); 7.5421 (4.9); 5.9457 (4.6); 5.9391 (4.5); 3.7437 (0.5); 3.7209 (1.7); 3.7081 (2.5); 3.6978 (5.0); 3.6902 (4.8); 3.6740 (1.1); 3.6666 (2.6); 3.6568 (1.3); 3.6431 (1.4); 3.6346 (1.6); 3.6253 (3.1); 3.6149 (2.0); 3.6035 (1.6); 3.5946 (2.2); 3.5841 (2.2); 3.5557 (2.2); 3.5324 (2.4); 3.5248 (1.8); 3.5090 (1.0); 3.5014 (1.8); 3.4692 (23.9); 3.4354 (30.6); 3.3161 (33.6); 3.0889 (2.2); 3.0578 (3.9); 3.0268 (1.8); 2.7329 (0.4); 2.7270 (0.6); 2.7210 (0.4); 2.5127 (33.8); 2.5069 (66.3); 2.5010 (87.3); 2.4951 (60.3); 2.3630 (1.6); 2.3380 (5.1); 2.3128 (5.3); 2.2876 (1.8); 2.2771 (0.6); 2.2707 (0.6); 2.2651 (0.4); 2.0740 (0.7); 1.2352 (0.4); 1.2061 (7.3); 1.1924 (11.9); 1.1829 (16.0); 1.1719 (11.4); 1.1597 (7.1); 1.0041 (7.3); 0.9790 (15.8); 0.9538 (6.9); 0.0107 (2.0); −0.0002 (53.7); −0.0112 (1.9) I-006 [00130]
I-006: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 10.8060 (1.8); 10.0490 (2.5); 7.9691 (6.0); 7.9473 (7.2); 7.7662 (0.9); 7.7584 (6.0); 7.7359 (7.7); 7.6173 (3.2); 7.5963 (3.0); 7.5726 (6.3); 7.5505 (5.2); 5.9443 (4.4); 5.9398 (4.4); 3.7305 (0.5); 3.7083 (2.9); 3.7022 (3.6); 3.6961 (4.1); 3.6905 (2.6); 3.6727 (2.1); 3.6551 (0.9); 3.6470 (1.0); 3.6190 (2.3); 3.6104 (2.3); 3.5954 (1.9); 3.5887 (1.7); 3.5632 (0.6); 3.5458 (1.9); 3.5283 (2.2); 3.5229 (1.7); 3.5052 (1.6); 3.4871 (0.8); 3.4684 (21.9); 3.4340 (27.4); 3.3334 (40.8); 3.0795 (2.0); 3.0562 (3.8); 3.0328 (1.7); 2.6752 (0.8); 2.6711 (1.0); 2.5062 (135.2); 2.5021 (176.8); 2.4979 (130.7); 2.3332 (0.9); 2.3289 (1.1); 2.0767 (0.4); 2.0357 (16.0); 1.2339 (0.4); 1.1996 (7.0); 1.1884 (11.9); 1.1823 (15.3); 1.1732 (11.2); 1.1649 (7.2); 1.1485 (0.5); 0.1458 (0.4); 0.0076 (4.3); −0.0003 (95.3); −0.0083 (3.7); −0.1498 (0.4) I-007 [00131]
I-007: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 10.7218 (4.2); 10.0286 (3.0); 7.9678 (6.4); 7.9462 (7.4); 7.7317 (6.4); 7.7093 (8.2); 7.6153 (4.0); 7.5944 (3.8); 7.5662 (6.2); 7.5446 (4.9); 5.9441 (4.8); 5.9401 (4.8); 3.7304 (0.7); 3.7128 (2.1); 3.7054 (3.2); 3.6969 (5.0); 3.6918 (4.4); 3.6725 (2.3); 3.6493 (1.4); 3.6331 (1.7); 3.6198 (2.8); 3.6117 (2.9); 3.5965 (2.4); 3.5900 (2.1); 3.5666 (0.9); 3.5492 (2.2); 3.5315 (2.5); 3.5263 (2.1); 3.5086 (2.0); 3.4906 (1.3); 3.4690 (23.0); 3.4351 (27.5); 3.4067 (0.7); 3.3189 (127.7); 3.2953 (3.5); 3.2561 (0.4); 3.0812 (2.2); 3.0579 (4.0); 3.0346 (1.9); 2.6701 (1.0); 2.5012 (127.1); 2.3516 (2.0); 2.3328 (5.8); 2.3141 (5.4); 2.2953 (2.0); 2.0739 (0.4); 1.2607 (0.5); 1.2345 (0.8); 1.2001 (7.7); 1.1895 (13.0); 1.1829 (16.0); 1.1743 (12.3); 1.1656 (7.4); 1.1356 (0.4); 1.0236 (0.4); 0.9965 (7.2); 0.9777 (14.1); 0.9589 (6.7); −0.0002 (12.4) I-008 [00132]
I-008: .sup.1H-NMR(300.1 MHz, d.sub.6-DMSO): δ = 10.7909 (2.3); 10.0469 (2.7); 7.9748 (5.2); 7.9456 (6.4); 7.7628 (5.4); 7.7558 (1.9); 7.7401 (2.2); 7.7327 (7.5); 7.7220 (0.8); 7.6228 (3.5); 7.5941 (3.2); 7.5743 (5.6); 7.5445 (4.1); 5.9749 (3.7); 5.9681 (3.7); 5.7576 (1.3); 4.0408 (0.6); 4.0171 (0.6); 3.7697 (1.9); 3.7603 (2.8); 3.7521 (2.0); 3.6815 (0.4); 3.6607 (0.9); 3.6399 (1.0); 3.6299 (1.2); 3.6090 (1.0); 3.5884 (0.4); 3.5330 (1.4); 3.5228 (1.4); 3.5024 (1.6); 3.4922 (1.6); 3.4483 (20.6); 3.4298 (26.3); 3.3974 (25.2); 3.3270 (360.8); 3.3033 (3.6); 3.1768 (0.9); 3.1593 (1.0); 3.0922 (1.8); 3.0611 (3.3); 3.0300 (1.4); 2.7337 (0.5); 2.7279 (0.7); 2.7216 (0.5); 2.5136 (41.4); 2.5077 (82.4); 2.5017 (109.6); 2.4958 (75.4); 2.4901 (34.6); 2.2778 (0.5); 2.2717 (0.6); 2.2654 (0.5); 2.0747 (0.5); 2.0362 (16.0); 1.9889 (2.6); 1.2612 (0.5); 1.2371 (0.4); 1.1967 (9.2); 1.1756 (9.4); 1.1508 (0.8); 1.0553 (0.4); 0.0107 (0.5); −0.0002 (14.1); −0.0112 (0.5) I-009 [00133]
I-009: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 11.8588 (2.3); 10.8427 (0.9); 10.0795 (2.3); 8.1930 (3.4); 8.0427 (16.0); 7.7812 (0.4); 7.7731 (3.3); 7.7677 (1.3); 7.7560 (1.3); 7.7505 (4.3); 7.7424 (0.5); 7.5794 (2.5); 7.5585 (2.1); 7.3793 (0.8); 7.3762 (0.9); 7.3571 (1.7); 7.3269 (0.7); 7.3227 (0.7); 7.3094 (1.0); 7.3058 (1.2); 7.2908 (0.6); 7.2862 (0.6); 7.2499 (0.5); 7.2461 (0.5); 7.2303 (1.3); 7.2267 (1.3); 7.2133 (1.2); 7.2072 (2.1); 7.2027 (1.9); 7.1875 (0.7); 7.1833 (0.5); 3.3338 (11.1); 3.1544 (0.7); 3.1373 (1.0); 3.1201 (0.7); 2.5259 (0.8); 2.5213 (1.1); 2.5123 (8.1); 2.5079 (16.9); 2.5034 (23.1); 2.4990 (16.9); 2.4946 (8.4); 2.0404 (8.2); 1.2351 (0.4); 1.2018 (9.9); 1.1846 (9.8); 0.0008 (3.6) I-010 [00134]
I-010: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 11.8733 (0.9); 10.8403 (0.4); 10.0699 (2.2); 8.1911 (3.8); 8.0402 (16.0); 7.7750 (2.8); 7.7700 (1.1); 7.7577 (1.2); 7.7526 (3.5); 7.7446 (0.4); 7.5783 (2.4); 7.5573 (2.0); 7.3014 (0.7); 7.2859 (1.2); 7.2781 (1.7); 7.2610 (1.7); 7.2525 (0.8); 7.2407 (2.0); 7.2364 (2.3); 7.2269 (2.0); 7.2203 (1.1); 7.2163 (1.1); 6.5497 (0.4); 3.3316 (39.1); 2.6720 (0.4); 2.5254 (2.5); 2.5207 (3.4); 2.5117 (24.7); 2.5074 (49.4); 2.5030 (65.6); 2.4985 (47.1); 2.4943 (22.3); 2.3299 (0.4); 2.2468 (9.8); 2.0393 (8.1); 0.0090 (0.4); 0.0009 (8.1) I-011 [00135]
I-011: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 11.8328 (1.4); 10.8392 (0.5); 9.9653 (1.8); 8.1811 (2.9); 8.0640 (0.3); 8.0412 (12.1); 8.0185 (0.4); 7.7733 (2.6); 7.7681 (1.0); 7.7563 (1.1); 7.7508 (3.4); 7.7429 (0.4); 7.5777 (2.1); 7.5568 (1.8); 7.1387 (0.9); 7.1287 (3.3); 7.1242 (4.8); 7.1136 (0.9); 7.1003 (0.4); 3.3310 (8.9); 2.5117 (7.2); 2.5074 (15.0); 2.5029 (20.5); 2.4985 (15.1); 2.4942 (7.5); 2.2015 (16.0); 2.0379 (7.0); 0.0090 (0.8); 0.0009 (20.7); −0.0074 (0.9) I-012 [00136]
I-012: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 11.8571 (1.4); 10.7932 (0.7); 10.0790 (2.7); 8.1925 (4.0); 8.0423 (16.0); 7.7617 (3.5); 7.7393 (4.2); 7.5780 (3.3); 7.5566 (2.7); 7.3791 (1.2); 7.3595 (2.2); 7.3266 (1.0); 7.3074 (1.5); 7.2909 (0.8); 7.2492 (0.7); 7.2298 (1.7); 7.2063 (2.7); 7.1865 (0.8); 3.3303 (16.2); 3.1726 (0.4); 3.1545 (0.8); 3.1374 (1.2); 3.1199 (0.9); 3.1027 (0.4); 2.6723 (0.4); 2.5036 (65.2); 2.3563 (1.0); 2.3374 (3.0); 2.3188 (2.9); 2.3004 (1.0); 1.2358 (1.3); 1.2020 (11.4); 1.1849 (11.0); 0.9967 (3.8); 0.9779 (7.5); 0.9591 (3.6); 0.0018 (45.7) I-013 [00137]
I-013: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 11.8582 (2.7); 11.1113 (1.4); 10.0798 (2.6); 8.1885 (3.6); 8.0407 (16.0); 7.7324 (3.3); 7.7272 (1.5); 7.7152 (1.7); 7.7099 (4.5); 7.5843 (3.0); 7.5634 (2.4); 7.3741 (1.1); 7.3567 (1.9); 7.3246 (0.8); 7.3206 (0.8); 7.3036 (1.3); 7.2882 (0.7); 7.2839 (0.7); 7.2469 (0.6); 7.2433 (0.6); 7.2273 (1.5); 7.2240 (1.4); 7.2102 (1.3); 7.2063 (1.6); 7.2019 (2.2); 7.1981 (2.1); 7.1825 (0.8); 3.3321 (15.3); 3.1502 (0.8); 3.1330 (1.1); 3.1159 (0.8); 3.0988 (0.3); 2.5400 (0.5); 2.5051 (24.2); 2.5007 (31.1); 2.4965 (23.1); 1.8400 (0.6); 1.8310 (0.7); 1.8206 (1.0); 1.8098 (0.7); 1.8010 (0.6); 1.2326 (0.4); 1.1983 (10.7); 1.1811 (10.5); 0.8444 (0.7); 0.8346 (1.6); 0.8266 (2.1); 0.8162 (1.8); 0.8074 (1.8); 0.6801 (1.0); 0.6717 (2.1); 0.6623 (2.5); 0.6538 (1.9); 0.6443 (0.8); −0.0017 (11.6) I-014 [00138]
I-014: .sup.1H-NMR(400.1 MHz, d.sub.6-DMSO): δ = 10.8408 (2.2); 10.6318 (4.4); 9.9907 (4.0); 8.1984 (4.1); 8.1775 (5.2); 8.0313 (5.8); 8.0101 (4.6); 7.7670 (4.8); 7.7447 (5.8); 7.5753 (4.9); 7.5540 (4.0); 7.3339 (1.9); 7.3181 (2.5); 7.2834 (2.3); 7.2775 (2.4); 7.2539 (0.9); 7.2337 (3.8); 7.2262 (4.2); 7.2175 (2.8); 7.1980 (0.5); 5.7599 (0.9); 3.3263 (17.4); 2.6306 (0.4); 2.5023 (47.6); 2.4178 (15.9); 2.3290 (0.4); 2.2490 (16.0); 2.0349 (13.6); 0.0007 (24.4) I-015 [00139]
I-015: .sup.1H-NMR(400.1 MHz, d.sub.6-DMSO): δ = 10.8431 (0.8); 10.5771 (1.9); 9.8804 (2.0); 8.2228 (2.3); 8.2017 (2.9); 8.0209 (2.9); 7.9996 (2.4); 7.7648 (2.5); 7.7424 (3.0); 7.5738 (2.5); 7.5526 (2.1); 7.1238 (5.2); 3.3262 (10.1); 2.5022 (36.5); 2.4121 (8.0); 2.2030 (16.0); 2.0319 (7.1); 0.0006 (21.3) I-016 [00140]
I-016: .sup.1H-NMR(400.1 MHz, d.sub.6-DMSO): δ = 10.7907 (0.8); 10.6146 (1.4); 9.9969 (3.9); 8.1972 (3.9); 8.1762 (5.2); 8.1083 (0.4); 8.0329 (5.7); 8.0118 (4.5); 7.7531 (4.8); 7.7309 (5.7); 7.5741 (4.9); 7.5531 (3.9); 7.3767 (1.8); 7.3583 (3.1); 7.3172 (1.4); 7.3018 (2.2); 7.2821 (1.3); 7.2636 (1.4); 7.2454 (5.5); 7.2287 (1.9); 7.2098 (0.6); 3.3297 (1.0); 3.1585 (0.5); 3.1419 (1.2); 3.1247 (1.6); 3.1077 (1.2); 3.0909 (0.5); 2.6310 (0.8); 2.5028 (19.7); 2.4217 (15.1); 2.3544 (1.5); 2.3361 (4.0); 2.3173 (3.9); 2.2986 (1.4); 1.2344 (1.9); 1.2045 (16.0); 1.1875 (15.4); 1.1502 (0.9); 0.9926 (5.0); 0.9738 (9.6); 0.9551 (4.6); 0.0006 (10.4) I-017 [00141]
I-017: .sup.1H-NMR(400.1 MHz, d.sub.6-DMSO): δ = 10.8257 (1.3); 10.5995 (2.5); 9.9858 (3.9); 8.1915 (3.8); 8.1708 (5.0); 8.1525 (0.4); 8.0297 (5.6); 8.0088 (4.6); 7.7671 (4.6); 7.7450 (5.7); 7.5722 (4.7); 7.5508 (3.9); 7.3753 (1.8); 7.3563 (3.1); 7.3174 (1.2); 7.3007 (2.1); 7.2810 (1.2); 7.2666 (1.2); 7.2461 (4.2); 7.2254 (1.9); 7.2073 (0.6); 5.7566 (0.6); 3.3148 (18.7); 3.2916 (0.4); 3.1588 (0.5); 3.1415 (1.2); 3.1245 (1.6); 3.1073 (1.2); 3.0902 (0.5); 2.6701 (0.3); 2.6296 (0.5); 2.5020 (57.2); 2.4206 (15.9); 2.3293 (0.4); 2.0349 (14.0); 1.2366 (1.2); 1.2044 (16.0); 1.1873 (15.9); 1.1510 (0.5); 0.0012 (35.7) I-018 [00142]
I-018: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 11.8250 (3.9); 10.0294 (3.6); 8.1780 (4.8); 8.0182 (2.6); 7.9968 (8.0); 7.9750 (6.3); 7.9537 (2.3); 7.7621 (0.5); 7.7554 (0.7); 7.7471 (5.2); 7.7418 (2.3); 7.7302 (2.2); 7.7247 (6.7); 7.7165 (0.8); 7.5657 (4.2); 7.5448 (3.3); 7.3723 (1.5); 7.3534 (3.0); 7.3214 (1.0); 7.3144 (1.1); 7.3067 (1.2); 7.3001 (1.6); 7.2883 (0.8); 7.2805 (0.9); 7.2481 (0.5); 7.2446 (0.4); 7.2282 (2.5); 7.2250 (3.0); 7.2199 (3.6); 7.2136 (4.6); 7.2117 (4.6); 7.2008 (0.6); 6.7718 (1.0); 4.0557 (0.6); 4.0378 (1.6); 4.0200 (1.6); 4.0022 (0.7); 3.8676 (0.4); 3.8481 (0.4); 3.8304 (0.3); 3.8254 (0.3); 3.7707 (0.4); 3.7604 (0.4); 3.7487 (0.4); 3.7259 (0.4); 3.7109 (0.4); 3.7086 (0.4); 3.6899 (0.4); 3.6870 (0.4); 3.6405 (0.3); 3.5681 (0.6); 3.1684 (0.6); 3.1506 (1.2); 3.1333 (1.6); 3.1162 (1.2); 3.0987 (0.5); 2.9268 (6.6); 2.9215 (6.5); 2.6755 (0.4); 2.6711 (0.5); 2.6667 (0.4); 2.5243 (1.3); 2.5107 (36.1); 2.5065 (72.0); 2.5021 (94.8); 2.4976 (71.1); 2.3334 (0.5); 2.3288 (0.6); 2.3246 (0.5); 1.9887 (6.1); 1.2011 (16.0); 1.1928 (4.6); 1.1839 (16.0); 1.1750 (4.9); 1.1571 (1.9); −0.0002 (1.8) I-019 [00143]
I-019: .sup.1H-NMR(600.4 MHz, d.sub.6-DMSO): δ = 11.8187 (3.5); 10.0217 (3.1); 8.1830 (4.1); 8.0250 (2.6); 8.0108 (6.7); 7.9918 (4.4); 7.9778 (1.9); 7.9133 (5.4); 7.9097 (1.7); 7.9020 (1.8); 7.8983 (5.9); 7.8928 (0.5); 7.5859 (3.1); 7.5719 (2.9); 7.3676 (1.4); 7.3548 (2.3); 7.3142 (0.9); 7.3098 (1.0); 7.3038 (1.0); 7.3001 (1.3); 7.2963 (0.7); 7.2914 (0.7); 7.2864 (0.8); 7.2385 (0.4); 7.2257 (2.0); 7.2234 (2.1); 7.2188 (2.8); 7.2139 (4.1); 7.2057 (0.5); 4.0477 (0.4); 4.0358 (1.2); 4.0238 (1.2); 4.0120 (0.4); 3.6936 (4.2); 3.6861 (5.0); 3.6780 (4.2); 3.3074 (138.1); 3.1532 (4.5); 3.1451 (5.8); 3.1375 (4.1); 3.1218 (1.1); 3.1104 (0.4); 2.6157 (0.4); 2.6125 (0.7); 2.6098 (0.5); 2.5218 (1.4); 2.5186 (1.6); 2.5155 (1.7); 2.5068 (35.5); 2.5038 (76.7); 2.5007 (106.6); 2.4977 (75.7); 2.4946 (34.1); 2.3877 (0.5); 2.3846 (0.6); 1.9875 (5.3); 1.2370 (0.3); 1.1983 (14.8); 1.1869 (16.0); 1.1753 (3.2); 1.1685 (0.7); 1.1635 (1.6); 1.1568 (0.5); 1.0701 (0.4); −0.0002 (8.1) I-020 [00144]
I-020: .sup.1H-NMR(600.4 MHz, d.sub.6-DMSO): δ = 11.8119 (3.4); 10.0136 (3.0); 8.1782 (4.0); 8.0084 (2.3); 7.9941 (6.0); 7.9768 (4.2); 7.9630 (1.8); 7.8223 (0.5); 7.8172 (4.3); 7.8134 (1.4); 7.8061 (1.6); 7.8023 (5.1); 7.7967 (0.6); 7.5822 (3.0); 7.5684 (2.7); 7.3653 (1.4); 7.3530 (2.2); 7.3121 (0.8); 7.3074 (1.0); 7.3019 (0.9); 7.2976 (1.2); 7.2888 (0.6); 7.2848 (0.7); 7.2348 (0.4); 7.2220 (2.2); 7.2189 (2.6); 7.2135 (3.9); 3.3171 (0.7); 3.3057 (145.5); 3.2007 (1.9); 3.1892 (6.2); 3.1775 (6.3); 3.1656 (2.0); 3.1440 (0.9); 3.1324 (1.2); 3.1213 (1.0); 3.1092 (0.4); 2.6125 (0.9); 2.6096 (0.7); 2.5327 (0.4); 2.5214 (1.8); 2.5185 (2.2); 2.5152 (2.1); 2.5063 (50.4); 2.5035 (107.4); 2.5005 (149.6); 2.4976 (108.5); 2.4947 (51.5); 2.3848 (0.8); 1.1975 (13.1); 1.1860 (13.2); 1.0470 (7.6); 1.0352 (16.0); 1.0234 (7.5); −0.0002 (9.7) I-021 [00145]
I-021: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 11.8124 (1.9); 10.0409 (2.3); 8.3161 (0.9); 8.1714 (4.0); 7.9662 (16.0); 7.7793 (0.4); 7.7711 (3.8); 7.7656 (1.3); 7.7542 (1.4); 7.7485 (4.9); 7.7404 (0.5); 7.5538 (2.6); 7.5332 (2.2); 7.3737 (0.8); 7.3704 (0.9); 7.3515 (1.7); 7.3212 (0.7); 7.3166 (0.8); 7.3038 (1.0); 7.3000 (1.1); 7.2852 (0.6); 7.2803 (0.7); 7.2443 (0.5); 7.2404 (0.5); 7.2247 (1.4); 7.2210 (1.4); 7.2044 (3.0); 7.1997 (2.0); 7.1850 (0.7); 7.1797 (0.5); 6.7153 (3.2); 3.3234 (93.7); 3.2992 (0.4); 3.1510 (0.7); 3.1341 (1.0); 3.1167 (0.8); 2.6795 (0.5); 2.6751 (1.1); 2.6705 (1.5); 2.6660 (1.1); 2.6614 (0.5); 2.5241 (4.6); 2.5194 (6.7); 2.5106 (90.1); 2.5062 (183.4); 2.5016 (239.8); 2.4970 (170.0); 2.4925 (80.4); 2.3377 (0.5); 2.3330 (1.1); 2.3284 (1.5); 2.3238 (1.1); 2.3194 (0.5); 1.1987 (10.9); 1.1815 (11.1); 1.1666 (0.9); 1.1411 (0.6); 1.1238 (0.6); 0.1458 (1.0); 0.0168 (0.4); 0.0080 (8.1); −0.0002 (250.8); −0.0086 (8.2); −0.1497 (1.0) I-022 [00146]
I-022: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 11.9081 (3.4); 10.0759 (3.4); 8.1954 (4.8); 8.1791 (0.5); 8.1333 (0.5); 8.1104 (0.6); 8.1024 (0.6); 8.0921 (1.3); 8.0699 (11.3); 8.0435 (1.4); 8.0218 (1.8); 8.0023 (1.9); 7.9600 (0.5); 7.9386 (0.4); 7.6062 (3.6); 7.5848 (3.2); 7.3782 (1.5); 7.3592 (3.0); 7.3282 (1.0); 7.3211 (1.2); 7.3135 (1.4); 7.3070 (1.6); 7.3012 (0.9); 7.2952 (0.9); 7.2873 (0.9); 7.2553 (0.5); 7.2522 (0.5); 7.2354 (2.7); 7.2322 (3.2); 7.2277 (3.6); 7.2209 (4.6); 7.2084 (0.8); 3.4686 (0.3); 3.4512 (0.7); 3.4337 (0.7); 3.4164 (0.4); 3.3209 (0.9); 3.1664 (0.6); 3.1496 (1.2); 3.1324 (1.6); 3.1151 (1.3); 3.0979 (0.5); 2.5075 (39.6); 2.5031 (49.2); 2.4987 (36.0); 2.0749 (3.3); 1.3060 (3.9); 1.2878 (7.9); 1.2694 (3.7); 1.2023 (16.0); 1.1851 (15.7); 1.1513 (0.4); 1.0750 (0.5); 1.0575 (1.0); 1.0401 (0.5); 0.0076 (1.4); −0.0002 (22.4) I-023 [00147]
I-023: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 9.3497 (0.4); 8.3448 (10.7); 8.3163 (0.8); 8.1691 (1.0); 8.0473 (7.7); 7.9564 (0.4); 7.8149 (9.0); 7.7939 (7.6); 7.7386 (3.0); 7.7271 (3.4); 7.7215 (11.9); 7.5668 (6.6); 7.5462 (5.4); 7.5249 (1.7); 7.5210 (2.0); 7.5053 (4.4); 7.5013 (4.3); 7.4904 (2.5); 7.4727 (3.0); 7.4698 (3.2); 7.4532 (1.3); 7.4499 (1.3); 7.3573 (1.7); 7.3529 (1.7); 7.3376 (3.2); 7.3334 (3.0); 7.3201 (2.2); 7.3159 (2.2); 7.2767 (4.5); 7.2737 (4.5); 7.2572 (2.8); 7.2540 (2.5); 6.7746 (0.9); 6.7638 (2.7); 6.7522 (2.7); 6.7411 (0.8); 4.2789 (4.0); 4.2356 (6.6); 4.1616 (7.0); 4.1182 (3.9); 3.3228 (33.7); 3.1740 (0.5); 3.1623 (0.6); 2.9514 (0.4); 2.9258 (16.0); 2.9143 (15.6); 2.8994 (0.4); 2.8903 (0.6); 2.817 (0.7); 2.8046 (1.8); 2.7874 (2.5); 2.7701 (1.9); 2.7528 (0.8); 2.7419 (0.5); 2.7316 (0.5); 2.6797 (1.0); 2.6751 (2.0); 2.6705 (2.7); 2.6613 (0.9); 2.5240 (8.6); 2.5192 (13.0); 2.5106 (156.9); 2.5061 (314.4); 2.5015 (411.9); 2.4969 (296.5); 2.4924 (140.4); 2.3374 (0.8); 2.3329 (1.8); 2.3284 (2.5); 2.3238 (1.8); 2.3194 (0.8); 1.2024 (0.4); 1.1687 (12.6); 1.1515 (13.0); 1.1427 (12.9); 1.1256 (12.0); 1.1042 (0.3); 0.0080 (0.4); −0.0002 (14.2); −0.0086 (0.4) I-024 [00148]
I-024: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 9.9101 (4.9); 8.3158 (0.5); 7.8286 (4.7); 7.8069 (7.0); 7.7553 (1.1); 7.7470 (8.7); 7.7416 (3.3); 7.7297 (5.0); 7.7243 (16.0); 7.7009 (4.8); 7.5339 (7.7); 7.5121 (8.7); 7.4811 (1.8); 7.4630 (2.7); 7.4450 (1.2); 7.3588 (1.4); 7.3556 (1.4); 7.3393 (2.8); 7.3213 (1.7); 7.3183 (1.6); 7.2687 (3.7); 7.2665 (3.6); 7.2492 (2.4); 6.6366 (8.5); 5.7559 (0.6); 4.2377 (2.6); 4.1927 (4.4); 4.1040 (4.9); 4.0590 (2.7); 3.3241 (48.0); 2.7508 (0.7); 2.7338 (1.7); 2.7168 (2.4); 2.6998 (1.8); 2.6806 (0.9); 2.6753 (1.0); 2.6707 (1.2); 2.6661 (1.0); 2.6618 (0.5); 2.5241 (4.0); 2.5192 (6.4); 2.5107 (70.4); 2.5062 (139.1); 2.5017 (181.0); 2.4971 (130.7); 2.4926 (63.0); 2.3376 (0.4); 2.3331 (0.8); 2.3285 (1.1); 2.3239 (0.8); 2.3195 (0.4); 1.1971 (8.5); 1.1801 (8.4); 1.1514 (0.7); 1.1241 (12.1); 1.1071 (11.8); 1.0451 (0.5); 1.0299 (0.5); −0.0002 (6.0) I-025 [00149]
I-025: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 9.9094 (4.5); 8.9068 (0.5); 8.3160 (2.8); 7.9181 (1.0); 7.8960 (1.2); 7.8638 (4.6); 7.8422 (9.4); 7.8257 (1.3); 7.8200 (4.1); 7.8120 (0.5); 7.7384 (1.6); 7.7264 (7.4); 7.7186 (10.5); 7.7133 (4.5); 7.7026 (6.8); 7.6962 (12.1); 7.6879 (1.4); 7.6471 (2.1); 7.6263 (1.7); 7.5753 (0.6); 7.5669 (1.2); 7.5448 (7.5); 7.5237 (5.7); 7.5130 (4.2); 7.4822 (1.8); 7.4643 (2.7); 7.4445 (1.2); 7.3600 (1.3); 7.3565 (1.4); 7.3374 (2.7); 7.3221 (1.6); 7.3193 (1.6); 7.2653 (3.7); 7.2482 (2.4); 6.6866 (1.1); 6.6755 (2.7); 6.6634 (2.5); 4.2402 (2.6); 4.1953 (4.3); 4.1070 (5.0); 4.0620 (2.8); 3.3238 (342.2); 3.3011 (1.4); 3.1202 (2.9); 3.0807 (2.6); 2.9238 (2.0); 2.9118 (3.1); 2.9053 (16.0); 2.8937 (16.0); 2.7495 (0.7); 2.7331 (1.8); 2.7162 (2.4); 2.6990 (1.8); 2.6798 (1.6); 2.6752 (2.7); 2.6705 (3.7); 2.6660 (2.8); 2.5241 (9.3); 2.5193 (13.7); 2.5106 (203.2); 2.5061 (424.5); 2.5016 (569.7); 2.4970 (417.5); 2.4926 (203.9); 2.4451 (0.5); 2.3375 (1.2); 2.3329 (2.5); 2.3284 (3.6); 2.3238 (2.6); 2.3193 (1.3); 1.1987 (8.3); 1.1817 (8.3); 1.1244 (11.6); 1.1074 (11.4); 0.1458 (4.7); 0.0295 (0.6); 0.0230 (0.8); 0.0079 (35.1); −0.0002 (1053.0); −0.0086 (40.4); −0.0519 (0.4); −0.1497 (4.7) I-026 [00150]
I-026: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 12.6212 (0.3); 10.0288 (3.6); 8.1043 (0.6); 8.0867 (0.4); 8.0813 (0.8); 8.0135 (2.1); 7.9494 (4.7); 7.9279 (6.2); 7.8139 (6.2); 7.7923 (4.9); 7.5858 (6.1); 7.5643 (5.6); 7.5340 (2.8); 7.5171 (5.3); 7.5145 (5.2); 7.4885 (2.4); 7.4704 (3.7); 7.4508 (1.6); 7.3650 (1.7); 7.3619 (1.8); 7.3451 (3.6); 7.3274 (2.1); 7.3245 (2.1); 7.2728 (5.0); 7.2533 (3.3); 7.2109 (0.4); 7.0833 (0.4); 6.9554 (0.4); 4.2590 (3.3); 4.2139 (5.6); 4.1208 (6.9); 4.0757 (4.0); 3.3520 (3.3); 2.7530 (0.9); 2.7360 (2.4); 2.7189 (3.3); 2.7018 (2.5); 2.6847 (1.0); 2.6759 (0.8); 2.6712 (1.0); 2.6667 (0.8); 2.5247 (2.3); 2.5199 (3.5); 2.5112 (53.6); 2.5068 (110.0); 2.5022 (145.3); 2.4977 (104.6); 2.4932 (50.0); 2.3835 (0.4); 2.3682 (0.4); 2.3336 (0.7); 2.3291 (0.9); 2.3246 (0.7); 1.2883 (6.0); 1.2701 (12.2); 1.2518 (5.8); 1.1989 (9.7); 1.1820 (9.6); 1.1280 (16.0); 1.1109 (15.7); 1.0698 (0.4); 0.1460 (1.5); 0.0234 (0.4); 0.0210 (0.5); 0.0079 (12.9); −0.0002 (345.4); −0.0086 (13.3); −0.0153 (0.9); −0.0160 (0.9); −0.0174 (0.8); −0.0226 (0.4); −0.1495 (1.5) I-027 [00151]
I-027: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 9.9124 (4.9); 7.8689 (5.0); 7.8472 (6.8); 7.7315 (13.2); 7.7092 (15.3); 7.5416 (8.0); 7.5291 (3.1); 7.5193 (7.2); 7.5131 (4.9); 7.4838 (1.8); 7.4652 (2.8); 7.4470 (1.3); 7.3600 (1.4); 7.3568 (1.4); 7.3404 (2.9); 7.3226 (1.7); 7.3195 (1.6); 7.2685 (3.9); 7.2490 (2.6); 6.6972 (2.5); 6.6855 (2.5); 6.6747 (0.9); 5.7560 (1.5); 4.2410 (2.7); 4.1960 (4.6); 4.1079 (5.2); 4.0628 (2.9); 3.3256 (64.4); 2.9107 (16.0); 2.8991 (15.8); 2.7514 (0.7); 2.7345 (1.8); 2.7174 (2.5); 2.7002 (1.9); 2.6828 (0.8); 2.6753 (0.8); 2.6706 (0.9); 2.6661 (0.8); 2.5240 (2.4); 2.5105 (53.4); 2.5061 (104.8); 2.5016 (134.8); 2.4971 (96.7); 2.4927 (46.4); 2.3330 (0.6); 2.3284 (0.8); 2.3239 (0.6); 1.1996 (8.8); 1.1826 (8.5); 1.1684 (1.1); 1.1513 (0.8); 1.1252 (12.0); 1.1081 (11.7); 0.1459 (0.7); 0.0079 (6.5); −0.0002 (171.3); −0.0085 (6.6); −0.1496 (0.7) I-028 [00152]
I-028: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 11.8938 (3.9); 10.0751 (3.8); 8.1916 (5.0); 8.1003 (5.2); 8.0826 (4.4); 8.0777 (6.8); 8.0612 (10.0); 8.0522 (7.7); 8.0308 (1.6); 7.5664 (4.0); 7.5448 (3.8); 7.3773 (1.6); 7.3585 (3.2); 7.3267 (1.1); 7.3196 (1.3); 7.3123 (1.4); 7.3057 (1.8); 7.2941 (0.9); 7.2859 (1.0); 7.2536 (0.6); 7.2306 (3.6); 7.2265 (4.1); 7.2195 (5.0); 7.2082 (0.8); 7.0953 (1.1); 6.9602 (2.4); 6.8250 (1.3); 3.7240 (1.6); 3.3879 (0.4); 3.1669 (0.6); 3.1496 (1.3); 3.1324 (1.7); 3.1152 (1.3); 3.0982 (0.6); 2.6754 (0.8); 2.6711 (1.0); 2.6671 (0.8); 2.5065 (123.1); 2.5022 (150.9); 2.4979 (114.0); 2.3333 (0.8); 2.3291 (1.0); 2.3247 (0.8); 1.2021 (16.0); 1.1849 (15.8); 1.1670 (1.2); 1.1493 (0.7); 0.1459 (0.6); −0.0002 (133.7); −0.1498 (0.7) I-029 [00153]
I-029: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 9.9118 (2.2); 9.1114 (0.4); 7.8695 (2.3); 7.8478 (3.1); 7.7327 (2.9); 7.7108 (2.3); 7.6934 (4.2); 7.6880 (1.5); 7.6765 (1.7); 7.6709 (5.6); 7.6626 (0.7); 7.6563 (0.3); 7.5295 (1.5); 7.5198 (3.3); 7.5139 (2.9); 7.4991 (2.6); 7.4852 (1.0); 7.4661 (1.3); 7.4450 (0.7); 7.4026 (0.4); 7.3803 (0.4); 7.3606 (0.7); 7.3572 (0.7); 7.3408 (1.3); 7.3231 (0.9); 7.3198 (0.9); 7.2681 (1.7); 7.2657 (1.7); 7.2486 (1.2); 7.0086 (1.9); 7.0032 (1.8); 6.6431 (0.3); 5.7560 (1.8); 4.2414 (1.2); 4.1964 (2.1); 4.1083 (2.4); 4.0631 (1.6); 4.0556 (1.3); 4.0378 (3.6); 4.0200 (3.7); 4.0022 (1.2); 3.3262 (51.6); 2.7671 (0.5); 2.7594 (0.8); 2.7504 (1.2); 2.7433 (1.1); 2.7345 (1.5); 2.7267 (0.7); 2.7174 (1.4); 2.7003 (0.9); 2.6831 (0.4); 2.6753 (0.4); 2.6706 (0.5); 2.6661 (0.4); 2.5241 (1.4); 2.5192 (2.1); 2.5107 (29.2); 2.5062 (59.6); 2.5017 (78.4); 2.4971 (56.0); 2.4926 (26.5); 2.3330 (0.4); 2.3286 (0.5); 2.3240 (0.4); 1.9888 (16.0); 1.2002 (4.0); 1.1927 (5.6); 1.1829 (4.2); 1.1750 (9.4); 1.1644 (0.9); 1.1571 (4.5); 1.1253 (5.6); 1.1082 (5.5); 0.6896 (0.6); 0.6715 (2.3); 0.6598 (2.2); 0.6538 (2.0); 0.6432 (0.8); 0.5732 (0.9); 0.5634 (2.5); 0.5559 (2.5); 0.5492 (1.9); 0.5360 (0.6); 0.0079 (0.8); −0.0002 (25.8); −0.0085 (0.9) I-030 [00154]
I-030: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 9.9495 (3.9); 9.5064 (3.8); 8.3156 (1.4); 7.9381 (4.1); 7.9163 (5.4); 7.8052 (0.3); 7.7741 (5.2); 7.7522 (4.3); 7.7357 (1.2); 7.7276 (8.2); 7.7222 (3.2); 7.7107 (3.3); 7.7050 (10.7); 7.6971 (1.4); 7.6727 (0.9); 7.5547 (5.9); 7.5341 (6.3); 7.5148 (3.4); 7.4857 (1.5); 7.4670 (2.3); 7.4486 (1.0); 7.3624 (1.2); 7.3588 (1.2); 7.3428 (2.4); 7.3250 (1.4); 7.3218 (1.4); 7.2710 (3.2); 7.2685 (3.2); 7.2515 (2.1); 5.7559 (2.1); 4.2445 (2.2); 4.1993 (3.7); 4.1095 (4.3); 4.0644 (2.4); 3.3281 (604.4); 2.7525 (0.6); 2.7353 (1.8); 2.7178 (3.4); 2.7110 (15.4); 2.6995 (16.0); 2.6802 (1.3); 2.6754 (2.3); 2.6709 (3.0); 2.6663 (2.3); 2.6616 (1.0); 2.5244 (8.1); 2.5197 (12.4); 2.5110 (172.4); 2.5065 (354.7); 2.5019 (468.4); 2.4973 (328.8); 2.4927 (150.5); 2.3378 (0.9); 2.3334 (2.0); 2.3287 (2.8); 2.3241 (2.0); 2.3194 (0.9); 1.2345 (0.7); 1.1991 (7.3); 1.1820 (7.2); 1.1259 (10.6); 1.1089 (10.5); 0.1459 (0.6); 0.0080 (5.6); −0.0002 (181.3); −0.0086 (5.2); −0.1495 (0.6) I-031 [00155]
I-031: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 10.0117 (3.7); 8.3163 (0.9); 8.0387 (0.4); 8.0103 (5.0); 8.0077 (7.9); 8.0054 (5.5); 7.9836 (3.9); 7.9618 (5.0); 7.8154 (4.8); 7.7936 (4.0); 7.7234 (0.4); 7.5966 (2.6); 7.5895 (1.6); 7.5805 (2.2); 7.5734 (16.0); 7.5628 (9.5); 7.5379 (3.8); 7.5152 (3.2); 7.4865 (1.4); 7.4678 (2.2); 7.4501 (1.0); 7.4255 (4.8); 7.4222 (8.5); 7.4188 (5.1); 7.3640 (1.1); 7.3607 (1.2); 7.3444 (2.3); 7.3265 (1.4); 7.3236 (1.4); 7.2730 (3.1); 7.2558 (2.0); 7.1128 (5.1); 7.1105 (6.6); 7.1096 (6.8); 7.1073 (5.3); 4.2503 (2.1); 4.2052 (3.6); 4.1158 (4.2); 4.0707 (2.3); 4.0375 (0.6); 4.0198 (0.6); 3.3230 (90.6); 2.7519 (0.6); 2.7351 (1.5); 2.7177 (2.2); 2.7008 (1.6); 2.6798 (1.1); 2.6751 (1.9); 2.6705 (2.6); 2.6660 (2.0); 2.5240 (6.4); 2.5193 (9.3); 2.5106 (139.8); 2.5061 (293.0); 2.5016 (392.0); 2.4970 (282.6); 2.4925 (134.4); 2.3374 (0.8); 2.3329 (1.7); 2.3283 (2.4); 2.3238 (1.7); 2.3195 (0.8); 1.9887 (2.4); 1.2495 (0.6); 1.2359 (0.8); 1.2011 (7.0); 1.1926 (3.2); 1.1841 (6.9); 1.1749 (2.7); 1.1570 (1.0); 1.1265 (10.7); 1.1094 (10.5); −0.0001 (11.4); −0.0085 (0.4) I-032 [00156]
I-032: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 10.8524 (0.9); 8.3807 (3.7); 8.0976 (2.6); 8.0766 (3.4); 7.8733 (3.1); 7.8523 (2.6); 7.7684 (3.1); 7.7629 (1.1); 7.7514 (1.3); 7.7457 (4.0); 7.7376 (0.4); 7.5753 (2.2); 7.5546 (1.9); 7.5263 (0.6); 7.5223 (0.7); 7.5065 (1.6); 7.5026 (1.6); 7.4915 (0.9); 7.4882 (0.9); 7.4738 (1.0); 7.4709 (1.2); 7.4544 (0.4); 7.4511 (0.5); 7.3591 (0.6); 7.3547 (0.6); 7.3394 (1.2); 7.3372 (1.0); 7.3352 (1.1); 7.3219 (0.8); 7.3177 (0.8); 7.2821 (1.6); 7.2791 (1.6); 7.2626 (1.0); 7.2594 (0.9); 5.7563 (0.6); 4.2882 (1.4); 4.2449 (2.2); 4.1688 (2.4); 4.1254 (1.3); 4.0560 (1.2); 4.0382 (3.5); 4.0204 (3.6); 4.0026 (1.2); 3.3272 (8.7); 2.8094 (0.6); 2.7924 (0.9); 2.7752 (0.6); 2.5249 (0.5); 2.5202 (0.7); 2.5115 (11.3); 2.5071 (23.3); 2.5025 (30.6); 2.4979 (21.7); 2.4933 (10.1); 2.0395 (7.6); 1.9891 (16.0); 1.1929 (4.5); 1.1751 (10.0); 1.1709 (4.6); 1.1573 (5.9); 1.1537 (4.8); 1.1453 (4.7); 1.1282 (4.3); −0.0002 (1.0) I-033 [00157]
I-033: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 9.9077 (2.2); 7.9992 (0.7); 7.9852 (1.3); 7.9717 (0.6); 7.8552 (2.2); 7.8334 (3.1); 7.7478 (0.5); 7.7395 (4.4); 7.7338 (2.2); 7.7283 (3.1); 7.7228 (2.7); 7.7170 (5.9); 7.7067 (2.4); 7.5508 (3.0); 7.5295 (3.3); 7.5126 (1.8); 7.5094 (1.8); 7.4819 (0.9); 7.4640 (1.2); 7.4469 (0.5); 7.3598 (0.6); 7.3563 (0.6); 7.3400 (1.2); 7.3221 (0.8); 7.3188 (0.7); 7.2673 (1.7); 7.2647 (1.7); 7.2478 (1.2); 7.2449 (1.0); 6.8310 (0.6); 6.8183 (1.3); 6.8048 (0.6); 5.7564 (2.4); 4.3490 (0.4); 4.3385 (0.4); 4.2407 (1.2); 4.1957 (2.0); 4.1071 (2.3); 4.0621 (1.3); 3.3966 (0.5); 3.3811 (1.5); 3.3668 (2.0); 3.3538 (1.2); 3.3260 (28.7); 3.3136 (2.3); 3.2990 (1.6); 3.2841 (0.4); 2.7329 (0.8); 2.7158 (1.2); 2.6987 (0.9); 2.6807 (0.4); 2.6753 (0.4); 2.6706 (0.5); 2.6660 (0.4); 2.5241 (1.1); 2.5193 (1.6); 2.5107 (26.0); 2.5062 (54.0); 2.5016 (71.5); 2.4970 (50.8); 2.4925 (23.9); 2.3284 (0.4); 1.7947 (16.0); 1.1980 (3.9); 1.1810 (3.8); 1.1245 (5.4); 1.1074 (5.2); 1.0451 (4.2); 1.0299 (4.2); −0.0002 (8.8) I-034 [00158]
I-034: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 10.7734 (1.7); 9.9740 (3.2); 7.9091 (3.2); 7.8875 (4.4); 7.7841 (4.2); 7.7623 (3.2); 7.7472 (0.8); 7.7390 (5.3); 7.7216 (2.3); 7.7165 (6.8); 7.7086 (0.8); 7.5564 (4.7); 7.5346 (5.0); 7.5134 (2.6); 7.4837 (1.2); 7.4656 (1.9); 7.4466 (0.8); 7.3596 (0.9); 7.3413 (1.9); 7.3237 (1.1); 7.2715 (2.6); 7.2527 (1.6); 5.7563 (3.2); 4.2452 (1.7); 4.2002 (2.8); 4.1103 (3.2); 4.0652 (1.8); 3.5679 (1.5); 3.3247 (44.7); 2.7525 (0.5); 2.7357 (1.2); 2.7188 (1.7); 2.7016 (1.3); 2.6843 (0.6); 2.6794 (0.5); 2.6750 (0.8); 2.6706 (1.1); 2.6663 (0.9); 2.5238 (3.6); 2.5061 (132.7); 2.5016 (170.8); 2.4972 (124.4); 2.3330 (0.8); 2.3285 (1.0); 2.3243 (0.8); 2.0252 (16.0); 1.1995 (5.8); 1.1824 (5.6); 1.1253 (8.2); 1.1082 (8.1); 0.1457 (0.7); 0.0078 (6.4); −0.0003 (165.9); −0.0086 (5.8); −0.1498 (0.7) I-035 [00159]
I-035: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 11.0445 (3.8); 9.9758 (6.2); 8.1427 (0.4); 7.9148 (6.2); 7.8930 (8.7); 7.7876 (8.2); 7.7658 (6.3); 7.7040 (10.0); 7.6989 (3.9); 7.6867 (4.5); 7.6815 (13.9); 7.6737 (1.8); 7.5623 (9.5); 7.5406 (7.6); 7.5133 (5.0); 7.4834 (2.4); 7.4652 (3.6); 7.4465 (1.6); 7.3592 (1.8); 7.3417 (3.7); 7.3244 (2.2); 7.2726 (5.0); 7.2541 (3.2); 5.7560 (7.8); 4.2454 (3.3); 4.2004 (5.6); 4.1113 (6.2); 4.0662 (3.4); 3.3298 (53.9); 3.1767 (0.8); 3.1637 (0.8); 2.7545 (0.9); 2.7378 (2.3); 2.7208 (3.2); 2.7036 (2.4); 2.6864 (1.0); 2.6756 (0.6); 2.6711 (0.8); 2.6668 (0.6); 2.5242 (2.5); 2.5106 (45.6); 2.5066 (88.5); 2.5022 (114.0); 2.4977 (82.7); 2.4936 (40.8); 2.3335 (0.5); 2.3290 (0.7); 2.3245 (0.5); 1.8403 (0.8); 1.8289 (1.6); 1.8200 (2.0); 1.8095 (3.2); 1.7985 (2.1); 1.7900 (1.7); 1.7785 (0.9); 1.2007 (11.0); 1.1837 (10.9); 1.1264 (16.0); 1.1094 (15.6); 0.8364 (1.7); 0.8264 (4.4); 0.8184 (6.0); 0.8078 (4.7); 0.7990 (5.0); 0.7909 (2.0); 0.6794 (2.4); 0.6710 (5.9); 0.6611 (7.2); 0.6529 (5.4); 0.6432 (1.7); 0.1457 (0.6); 0.0079 (5.2); −0.0002 (129.5); −0.0085 (5.0); −0.1497 (0.6) I-036 [00160]
I-036: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 10.7221 (3.1); 9.9751 (3.2); 7.9130 (3.2); 7.8912 (4.6); 7.7865 (4.3); 7.7647 (3.3); 7.7486 (0.4); 7.7326 (0.7); 7.7247 (6.2); 7.7194 (2.2); 7.7077 (2.4); 7.7021 (7.9); 7.6941 (0.8); 7.5552 (4.8); 7.5342 (5.2); 7.5138 (2.8); 7.4841 (1.3); 7.4657 (1.9); 7.4456 (0.9); 7.3590 (1.0); 7.3419 (1.9); 7.3247 (1.1); 7.3220 (1.1); 7.2716 (2.6); 7.2542 (1.6); 4.2454 (1.8); 4.2003 (3.0); 4.1111 (3.4); 4.0661 (1.9); 3.3272 (39.6); 2.7544 (0.4); 2.7374 (1.2); 2.7203 (1.7); 2.7032 (1.3); 2.6860 (0.5); 2.6756 (0.5); 2.6710 (0.6); 2.6666 (0.4); 2.5245 (1.6); 2.5197 (2.7); 2.5111 (34.6); 2.5067 (70.2); 2.5021 (91.3); 2.4975 (64.8); 2.4931 (30.5); 2.3444 (1.4); 2.3256 (4.9); 2.3068 (4.7); 2.2879 (1.6); 2.0743 (1.2); 1.2006 (5.8); 1.1836 (5.7); 1.1263 (8.7); 1.1093 (8.5); 0.9924 (7.5); 0.9736 (16.0); 0.9547 (7.2); 0.1459 (0.4); 0.0080 (3.8); −0.0002 (107.1); −0.0085 (3.4); −0.1496 (0.4) I-037 [00161]
I-037: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 11.6441 (2.1); 9.9884 (4.2); 8.3143 (0.3); 7.9221 (3.3); 7.9007 (4.5); 7.7978 (5.5); 7.7747 (7.6); 7.7513 (5.5); 7.7252 (0.4); 7.5925 (5.7); 7.5714 (4.7); 7.5319 (2.0); 7.5149 (3.6); 7.5126 (3.5); 7.4842 (1.6); 7.4665 (2.5); 7.4477 (1.1); 7.3627 (1.3); 7.3596 (1.3); 7.3430 (2.6); 7.3252 (1.5); 7.3222 (1.5); 7.2737 (3.5); 7.2715 (3.5); 7.2543 (2.3); 4.3276 (0.3); 4.3109 (1.4); 4.2937 (3.5); 4.2760 (3.5); 4.2584 (1.5); 4.2472 (2.6); 4.2021 (4.0); 4.1133 (4.7); 4.0682 (2.6); 3.3267 (97.0); 2.7545 (0.7); 2.7377 (1.7); 2.7207 (2.4); 2.7035 (1.8); 2.6866 (0.7); 2.6801 (0.4); 2.6755 (0.6); 2.6708 (0.9); 2.6664 (0.6); 2.5244 (2.3); 2.5197 (3.4); 2.5110 (43.7); 2.5065 (89.4); 2.5019 (120.0); 2.4972 (88.0); 2.4927 (42.4); 2.3333 (0.5); 2.3287 (0.8); 2.3241 (0.6); 2.0737 (16.0); 1.3215 (0.6); 1.2751 (4.1); 1.2010 (7.6); 1.1840 (7.4); 1.1265 (12.2); 1.1094 (12.0); 0.1459 (0.4); 0.0080 (3.2); −0.0002 (103.7); −0.0085 (3.3);-0.1496 (0.4) I-038 [00162]
I-038: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 11.7883 (1.1); 9.9920 (5.2); 8.3146 (0.4); 8.1331 (0.3); 7.9348 (4.9); 7.9133 (6.6); 7.8016 (7.4); 7.7798 (6.3); 7.7587 (2.9); 7.7397 (3.2); 7.5884 (8.8); 7.5676 (7.0); 7.5324 (2.6); 7.5155 (4.7); 7.5132 (4.6); 7.4846 (2.2); 7.4670 (3.3); 7.4490 (1.4); 7.3632 (1.7); 7.3601 (1.7); 7.3436 (3.4); 7.3257 (2.0); 7.3227 (2.0); 7.2740 (4.6); 7.2719 (4.6); 7.2547 (3.0); 6.5881 (0.6); 6.4557 (1.3); 6.3224 (0.6); 4.2483 (3.2); 4.2033 (5.3); 4.1139 (6.2); 4.0689 (3.5); 3.3256 (36.8); 2.7549 (0.9); 2.7381 (2.3); 2.7210 (3.2); 2.7038 (2.4); 2.6867 (0.9); 2.6800 (0.5); 2.6754 (0.8); 2.6707 (1.1); 2.6663 (0.8); 2.6616 (0.4); 2.5243 (2.9); 2.5196 (4.4); 2.5109 (54.5); 2.5064 (111.6); 2.5017 (151.6); 2.4971 (113.2); 2.4926 (55.4); 2.3377 (0.3); 2.3332 (0.7); 2.3286 (1.0); 2.3240 (0.7); 2.0736 (9.8); 1.2012 (9.8); 1.1842 (9.7); 1.1271 (16.0); 1.1100 (15.8); 0.1459 (0.5); 0.0080 (3.9); −0.0002 (118.9); −0.0085 (3.8); −0.1496 (0.5) I-039 [00163]
I-039: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 10.1224 (4.2); 8.3384 (9.6); 8.3150 (1.3); 7.9425 (5.4); 7.9217 (7.4); 7.8418 (0.4); 7.8205 (0.9); 7.8172 (1.0); 7.8039 (7.7); 7.7952 (1.9); 7.7829 (5.9); 7.7619 (0.8); 7.7346 (5.6); 7.7123 (7.2); 7.5655 (5.3); 7.5441 (4.2); 7.5232 (1.9); 7.5196 (2.2); 7.5036 (4.5); 7.4999 (4.6); 7.4890 (2.4); 7.4861 (2.4); 7.4712 (3.0); 7.4686 (3.2); 7.4519 (1.2); 7.4487 (1.2); 7.3561 (1.5); 7.3518 (1.5); 7.3364 (3.1); 7.3324 (3.0); 7.3189 (2.1); 7.3148 (2.1); 7.3085 (0.3); 7.2749 (4.2); 7.2721 (4.4); 7.2555 (2.6); 7.2524 (2.6); 6.9749 (6.6); 5.9865 (0.7); 5.6046 (0.5); 4.2765 (3.5); 4.2332 (5.9); 4.1590 (6.4); 4.1328 (0.4); 4.1157 (3.5); 4.0557 (0.5); 4.0379 (1.4); 4.0201 (1.4); 4.0024 (0.5); 3.3238 (222.1); 2.8254 (0.7); 2.8087 (1.8); 2.7916 (2.5); 2.7744 (1.8); 2.7578 (0.7); 2.6752 (1.2); 2.6706 (1.7); 2.6661 (1.2); 2.5240 (5.4); 2.5192 (8.1); 2.5106 (100.5); 2.5062 (201.4); 2.5017 (263.2); 2.4971 (191.9); 2.4927 (94.3); 2.3376 (0.5); 2.3330 (1.2); 2.3285 (1.6); 2.3240 (1.2); 2.0241 (16.0); 1.9884 (6.1); 1.3978 (6.6); 1.3515 (1.1); 1.3359 (0.7); 1.2984 (0.3); 1.2585 (0.6); 1.2494 (1.2); 1.2350 (2.6); 1.1927 (1.8); 1.1748 (5.7); 1.1697 (12.4); 1.1526 (12.9); 1.1438 (13.1); 1.1266 (12.2); 1.0998 (0.6); 1.0829 (0.5); 0.8538 (0.5); 0.1460 (1.0); 0.0079 (8.0); −0.0002 (235.8); −0.0085 (8.6); −0.1495 (1.0) I-040 [00164]
I-040: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 11.7907 (3.8); 10.1029 (3.0); 10.0139 (3.7); 8.3100 (0.5); 8.1683 (4.6); 7.9673 (2.7); 7.9462 (5.2); 7.9049 (5.3); 7.8838 (2.9); 7.7357 (3.5); 7.7133 (4.5); 7.5595 (3.3); 7.5384 (2.6); 7.3685 (1.5); 7.3495 (2.9); 7.3171 (1.0); 7.3072 (1.6); 7.2957 (1.6); 7.2869 (1.2); 7.2760 (1.0); 7.2237 (5.7); 7.2145 (4.4); 6.9887 (4.0); 5.7499 (13.2); 4.0384 (0.5); 4.0206 (0.6); 3.3135 (173.0); 3.1711 (0.4); 3.1542 (1.0); 3.1369 (1.5); 3.1197 (1.1); 3.1026 (0.4); 2.6745 (0.7); 2.6699 (0.9); 2.6653 (0.7); 2.5234 (3.0); 2.5187 (4.4); 2.5101 (49.8); 2.5055 (102.6); 2.5008 (140.5); 2.4962 (105.5); 2.4917 (52.1); 2.3324 (0.6); 2.3278 (0.9); 2.3232 (0.7); 2.0234 (10.0); 1.9875 (2.5); 1.9082 (1.1); 1.2358 (0.5); 1.2015 (16.0); 1.1932 (2.6); 1.1843 (15.9); 1.1754 (2.3); 1.1677 (1.4); 1.1575 (0.9); 1.1505 (1.2); 1.0699 (0.5); 0.1459 (0.4); 0.0081 (3.1); −0.0002 (103.5); −0.0085 (3.6); −0.1495 (0.4) I-041 [00165]
I-041: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 9.9001 (7.0); 7.8436 (6.9); 7.8224 (9.4); 7.7760 (0.3); 7.7171 (16.0); 7.6948 (15.9); 7.5495 (10.0); 7.5284 (11.0); 7.5106 (6.6); 7.4824 (3.1); 7.4642 (4.4); 7.4448 (2.0); 7.3570 (2.3); 7.3386 (4.5); 7.3204 (2.7); 7.2646 (5.8); 7.2455 (3.8); 6.9609 (4.5); 6.9416 (4.6); 4.3425 (0.4); 4.3221 (1.6); 4.3020 (2.9); 4.2824 (3.0); 4.2616 (1.8); 4.2396 (3.7); 4.1945 (6.0); 4.1065 (6.5); 4.0615 (3.5); 3.3242 (138.9); 2.7498 (1.1); 2.7329 (2.6); 2.7159 (3.5); 2.6989 (2.7); 2.6802 (1.6); 2.6705 (1.8); 2.5013 (233.0); 2.3283 (1.7); 2.2778 (4.5); 2.2695 (4.6); 2.2601 (4.7); 2.1053 (1.1); 2.0819 (3.6); 2.0570 (5.1); 2.0332 (3.5); 2.0092 (1.1); 1.6747 (1.9); 1.6623 (3.5); 1.6518 (4.0); 1.6374 (5.0); 1.6175 (3.0); 1.5919 (0.9); 1.1977 (12.5); 1.1809 (12.4); 1.1242 (15.4); 1.1073 (15.1); −0.0004 (18.8) I-042 [00166]
I-042: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 9.9021 (3.3); 8.3147 (0.3); 8.1485 (0.4); 7.8544 (3.2); 7.8326 (4.6); 7.7240 (4.7); 7.7192 (8.2); 7.7137 (2.9); 7.7022 (5.6); 7.6965 (9.2); 7.6884 (1.0); 7.5485 (4.5); 7.5280 (4.8); 7.5123 (2.7); 7.5091 (2.7); 7.4823 (1.2); 7.4646 (1.8); 7.4449 (0.8); 7.3597 (0.9); 7.3561 (1.0); 7.3401 (1.9); 7.3222 (1.1); 7.3188 (1.1); 7.2666 (2.5); 7.2639 (2.6); 7.2471 (1.7); 7.2444 (1.6); 6.7271 (1.1); 6.7135 (2.2); 6.6996 (1.1); 4.2398 (1.8); 4.1948 (3.1); 4.1068 (3.6); 4.0618 (2.0); 3.3931 (0.8); 3.3755 (2.6); 3.3611 (3.0); 3.3578 (3.1); 3.3435 (3.2); 3.3249 (98.8); 2.7507 (0.4); 2.7337 (1.2); 2.7167 (1.7); 2.6996 (1.3); 2.6812 (0.6); 2.6751 (0.7); 2.6705 (0.9); 2.6659 (0.7); 2.6618 (0.3); 2.5241 (2.4); 2.5193 (3.7); 2.5106 (51.6); 2.5061 (106.4); 2.5016 (140.8); 2.4969 (102.5); 2.4924 (50.1); 2.3329 (0.6); 2.3284 (0.9); 2.3238 (0.6); 2.0737 (7.6); 1.2072 (7.6); 1.1987 (6.2); 1.1894 (16.0); 1.1818 (6.3); 1.1716 (7.3); 1.1248 (8.0); 1.1077 (7.9); 0.0080 (1.2); −0.0002 (41.8); −0.0085 (1.5) I-043 [00167]
I-043: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 9.9009 (2.4); 8.1360 (0.7); 7.8501 (2.4); 7.8284 (3.4); 7.7242 (3.6); 7.7163 (5.3); 7.7106 (2.1); 7.6997 (3.1); 7.6936 (6.3); 7.6855 (0.6); 7.5468 (3.3); 7.5266 (3.3); 7.5118 (2.1); 7.5087 (2.0); 7.4838 (0.9); 7.4649 (1.3); 7.4465 (0.6); 7.3595 (0.7); 7.3559 (0.7); 7.3399 (1.4); 7.3221 (0.8); 7.3186 (0.8); 7.2666 (1.9); 7.2469 (1.3); 6.4938 (1.5); 6.4745 (1.6); 4.2400 (1.3); 4.1949 (2.3); 4.1069 (2.6); 4.0619 (1.5); 4.0248 (0.6); 4.0083 (0.9); 3.9897 (0.9); 3.9732 (0.6); 3.3251 (31.8); 2.7512 (0.3); 2.7344 (0.9); 2.7173 (1.3); 2.7002 (1.0); 2.6827 (0.4); 2.6705 (0.4); 2.6658 (0.3); 2.5240 (1.2); 2.5193 (1.8); 2.5106 (23.7); 2.5061 (47.5); 2.5015 (61.6); 2.4969 (43.6); 2.4924 (20.5); 2.3283 (0.4); 2.0739 (6.0); 1.2295 (16.0); 1.2133 (16.0); 1.1989 (4.4); 1.1818 (4.2); 1.1250 (5.8); 1.1079 (5.7); −0.0002 (5.6) I-044 [00168]
I-044: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 9.9046 (2.2); 8.1330 (1.0); 7.8513 (2.2); 7.8295 (3.1); 7.7262 (2.9); 7.7153 (0.8); 7.7069 (5.7); 7.6901 (1.7); 7.6844 (5.9); 7.6763 (0.6); 7.5557 (3.0); 7.5331 (2.8); 7.5121 (1.8); 7.5091 (1.8); 7.4819 (0.8); 7.4645 (1.2); 7.4464 (0.6); 7.3596 (0.6); 7.3562 (0.6); 7.3400 (1.3); 7.3222 (0.8); 7.3187 (0.7); 7.2669 (1.7); 7.2644 (1.7); 7.2475 (1.2); 7.2447 (1.0); 6.7545 (0.7); 6.7405 (1.4); 6.7265 (0.7); 5.2581 (1.1); 4.2401 (1.2); 4.1951 (2.1); 4.1067 (2.4); 4.0616 (1.4); 3.5860 (1.1); 3.5685 (3.6); 3.5546 (2.5); 3.5025 (1.1); 3.4932 (2.4); 3.4894 (2.5); 3.4759 (6.1); 3.4585 (5.1); 3.4411 (1.5); 3.3218 (18.4); 2.7513 (0.3); 2.7343 (0.8); 2.7172 (1.2); 2.7000 (0.9); 2.6825 (0.4); 2.6750 (0.4); 2.6703 (0.6); 2.6658 (0.4); 2.5239 (1.6); 2.5192 (2.3); 2.5105 (31.4); 2.5060 (63.8); 2.5014 (83.5); 2.4968 (59.3); 2.4922 (28.0); 2.3328 (0.4); 2.3282 (0.5); 2.3236 (0.4); 2.0738 (2.2); 1.1986 (3.9); 1.1816 (3.8); 1.1248 (5.9); 1.1201 (6.5); 1.1076 (6.1); 1.1026 (11.4); 1.0851 (5.0); 0.8491 (0.7); 0.8421 (16.0); 0.8350 (0.7); −0.0002 (7.9); −0.0340 (0.4); −0.0418 (11.7); −0.0497 (0.4) I-045 [00169]
I-045: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 9.9034 (5.8); 8.3144 (0.4); 8.1358 (1.7); 7.9114 (0.4); 7.8894 (0.5); 7.8576 (5.6); 7.8360 (7.8); 7.7559 (0.6); 7.7356 (12.7); 7.7301 (10.9); 7.7188 (5.4); 7.7132 (16.0); 7.5679 (0.6); 7.5463 (8.3); 7.5261 (7.9); 7.5116 (5.1); 7.5089 (4.9); 7.4822 (2.2); 7.4644 (3.3); 7.4457 (1.5); 7.3594 (1.6); 7.3562 (1.6); 7.3395 (3.4); 7.3219 (2.0); 7.3188 (1.9); 7.2655 (4.5); 7.2636 (4.5); 7.2461 (3.0); 6.8564 (4.2); 6.8419 (4.3); 4.4119 (0.4); 4.3998 (1.1); 4.3854 (1.9); 4.3701 (1.8); 4.3667 (1.9); 4.3522 (1.1); 4.3401 (0.4); 4.2400 (3.1); 4.1950 (5.3); 4.1067 (6.0); 4.0617 (3.4); 3.9589 (3.1); 3.9432 (3.3); 3.9365 (4.0); 3.9210 (3.2); 3.8665 (1.3); 3.8472 (3.3); 3.8284 (3.8); 3.8100 (1.8); 3.7462 (1.8); 3.7314 (2.2); 3.7262 (3.3); 3.7115 (3.2); 3.7062 (1.7); 3.6913 (1.4); 3.6581 (3.5); 3.6467 (3.5); 3.6358 (3.1); 3.6245 (2.9); 3.3194 (38.3); 2.7507 (0.8); 2.7340 (2.1); 2.7168 (3.0); 2.6997 (2.2); 2.6823 (0.9); 2.6746 (0.9); 2.6699 (1.2); 2.6656 (1.0); 2.5234 (3.5); 2.5099 (69.7); 2.5055 (138.5); 2.5010 (181.2); 2.4965 (132.6); 2.4921 (65.5); 2.3323 (0.9); 2.3279 (1.2); 2.3234 (0.8); 2.2456 (0.8); 2.2263 (1.8); 2.2135 (1.4); 2.2089 (1.9); 2.1947 (2.3); 2.1772 (2.2); 2.1583 (0.8); 2.0734 (15.3); 1.9967 (0.9); 1.9831 (1.4); 1.9652 (2.1); 1.9513 (2.0); 1.9387 (1.0); 1.9339 (1.0); 1.9198 (0.7); 1.1981 (9.9); 1.1811 (9.8); 1.1249 (13.7); 1.1078 (13.4); 0.0079 (0.7); −0.0003 (22.4); −0.0086 (0.8) I-046 [00170]
I-046: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 9.9459 (2.7); 7.8801 (2.6); 7.8586 (3.6); 7.7746 (4.6); 7.7581 (5.4); 7.7527 (6.9); 7.7382 (2.9); 7.5827 (3.9); 7.5613 (3.3); 7.5293 (1.4); 7.5103 (2.4); 7.4827 (1.1); 7.4644 (1.7); 7.4452 (0.8); 7.3572 (0.9); 7.3383 (1.7); 7.3210 (1.0); 7.2651 (2.3); 7.2461 (1.5); 4.2423 (1.3); 4.1973 (2.4); 4.1093 (2.7); 4.0641 (1.4); 3.3157 (51.6); 3.1833 (16.0); 3.1526 (15.8); 3.1345 (0.7); 2.7490 (0.4); 2.7317 (1.0); 2.7150 (1.4); 2.6980 (1.1); 2.6701 (1.2); 2.5011 (179.6); 2.3278 (1.2); 2.0730 (0.8); 1.1967 (4.8); 1.1798 (4.7); 1.1237 (6.6); 1.1067 (6.4); −0.0002 (18.9) I-047 [00171]
I-047: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 8.3426 (9.1); 8.0392 (6.8); 8.0185 (8.5); 7.8136 (8.1); 7.7928 (6.9); 7.7438 (7.4); 7.7215 (9.3); 7.5698 (6.6); 7.5485 (5.3); 7.5200 (1.9); 7.5035 (4.4); 7.5007 (4.4); 7.4870 (2.6); 7.4695 (3.3); 7.4498 (1.3); 7.3565 (1.4); 7.3526 (1.5); 7.3367 (3.1); 7.3194 (2.0); 7.3158 (2.0); 7.2739 (4.5); 7.2563 (2.6); 6.8220 (1.7); 6.8087 (3.3); 6.7949 (1.7); 4.2776 (3.1); 4.2342 (5.6); 4.1612 (5.8); 4.1178 (3.0); 3.4153 (1.1); 3.3978 (3.5); 3.3815 (4.4); 3.3658 (3.6); 3.3371 (13.7); 2.8235 (0.7); 2.8066 (1.7); 2.7896 (2.3); 2.7726 (1.8); 2.7554 (0.7); 2.6708 (0.5); 2.6667 (0.4); 2.5059 (68.7); 2.5019 (86.1); 2.4978 (66.3); 2.3287 (0.5); 1.2205 (8.1); 1.2028 (16.0); 1.1849 (8.2); 1.1696 (11.8); 1.1524 (12.6); 1.1435 (12.6); 1.1263 (11.2); −0.0002 (26.6) I-048 [00172]
I-048: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 8.3404 (5.5); 8.0316 (3.8); 8.0107 (5.0); 7.8111 (4.5); 7.7901 (3.8); 7.7465 (0.4); 7.7382 (4.6); 7.7327 (1.7); 7.7213 (1.7); 7.7156 (6.2); 7.7075 (0.6); 7.5678 (3.2); 7.5473 (2.6); 7.5243 (0.8); 7.5202 (1.0); 7.5044 (2.2); 7.5004 (2.2); 7.4899 (1.3); 7.4866 (1.3); 7.4722 (1.5); 7.4692 (1.6); 7.4528 (0.6); 7.4493 (0.7); 7.3566 (0.9); 7.3522 (0.9); 7.3369 (1.6); 7.3327 (1.6); 7.3194 (1.2); 7.3152 (1.2); 7.2750 (2.3); 7.2721 (2.3); 7.2555 (1.5); 7.2523 (1.3); 6.5936 (1.7); 6.5743 (1.8); 4.2772 (2.1); 4.2339 (3.3); 4.1605 (3.6); 4.1171 (2.0); 4.0478 (0.6); 4.0313 (0.9); 4.0122 (0.9); 3.9959 (0.6); 3.3230 (89.2); 2.822 (0.3); 2.8054 (0.9); 2.7883 (1.2); 2.7711 (0.9); 2.7543 (0.3); 2.6753 (0.6); 2.6706 (0.9); 2.6661 (0.6); 2.5242 (2.9); 2.5195 (4.3); 2.5108 (53.1); 2.5063 (108.6); 2.5017 (142.4); 2.4970 (101.3); 2.4925 (48.1); 2.3332 (0.6); 2.3285 (0.9); 2.3239 (0.6); 1.2414 (16.0); 1.2251 (15.9); 1.1690 (6.4); 1.1519 (6.6); 1.1428 (6.6); 1.1257 (6.2); 0.1460 (0.3); 0.0080 (3.0); −0.0002 (96.1); −0.0085 (3.1); −0.1495 (0.4) I-049 [00173]
I-049: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 11.8326 (2.7); 10.0223 (2.5); 8.1719 (3.6); 7.9923 (0.3); 7.9704 (16.0); 7.8050 (0.4); 7.7968 (3.7); 7.7913 (1.3); 7.7798 (1.5); 7.7742 (4.8); 7.7660 (0.5); 7.5885 (2.8); 7.5677 (2.3); 7.5440 (1.6); 7.5284 (1.6); 7.3711 (1.0); 7.3526 (2.1); 7.3210 (0.7); 7.3135 (0.8); 7.3069 (0.8); 7.2996 (1.1); 7.2933 (0.5); 7.2883 (0.5); 7.2800 (0.6); 7.2286 (1.7); 7.2251 (2.2); 7.2215 (2.5); 7.2144 (3.1); 7.2127 (3.1); 7.2023 (0.3); 4.9538 (0.5); 4.9362 (1.0); 4.9200 (1.1); 4.9024 (0.8); 4.8155 (2.2); 4.7992 (3.6); 4.7815 (1.8); 4.6323 (2.3); 4.6159 (4.3); 4.6002 (2.0); 3.3246 (4.7); 3.1494 (0.7); 3.1323 (1.0); 3.1151 (0.8); 2.5243 (0.7); 2.5109 (12.5); 2.5065 (24.8); 2.5020 (32.0); 2.4974 (23.1); 2.4930 (11.1); 1.2004 (10.9); 1.1832 (10.7); 0.0080 (0.8); −0.0002 (22.5); −0.0085 (0.8) I-050 [00174]
I-050: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 11.8257 (2.9); 10.0232 (2.6); 8.1773 (3.5); 8.0094 (1.8); 7.9878 (6.4); 7.9701 (4.9); 7.9486 (1.5); 7.7542 (0.4); 7.7459 (4.1); 7.7404 (1.4); 7.7290 (1.6); 7.7233 (5.3); 7.7152 (0.6); 7.5677 (2.9); 7.5471 (2.4); 7.3716 (1.1); 7.3528 (2.2); 7.3207 (0.7); 7.3125 (0.9); 7.3073 (0.8); 7.2993 (1.1); 7.2921 (0.6); 7.2889 (0.6); 7.2797 (0.7); 7.2289 (2.0); 7.2252 (3.0); 7.2155 (3.3); 7.2135 (3.1); 6.8116 (0.8); 6.7978 (1.6); 6.7837 (0.8); 5.7552 (0.4); 3.4184 (0.5); 3.4007 (1.6); 3.3863 (1.9); 3.3831 (1.8); 3.3688 (1.6); 3.3512 (0.5); 3.3241 (11.8); 3.1520 (0.8); 3.1348 (1.1); 3.1176 (0.8); 2.5244 (0.8); 2.5196 (1.2); 2.5110 (16.8); 2.5065 (33.4); 2.5019 (43.1); 2.4973 (30.5); 2.4929 (14.5); 2.0740 (16.0); 1.2229 (4.5); 1.2049 (13.4); 1.2019 (13.2); 1.1847 (12.6); 0.0080 (1.8); −0.0002 (52.5); −0.0085 (1.9) I-051 [00175]
I-051: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 11.8269 (3.8); 10.0421 (0.4); 10.0221 (3.5); 8.1795 (4.7); 8.1479 (0.5); 8.1365 (4.2); 8.0225 (2.8); 8.0011 (8.0); 7.9767 (6.0); 7.9554 (2.3); 7.9027 (0.4); 7.8831 (0.4); 7.7270 (0.5); 7.7188 (5.5); 7.7133 (1.9); 7.7019 (2.2); 7.6962 (7.6); 7.6881 (0.8); 7.6778 (0.5); 7.5381 (3.9); 7.5175 (3.1); 7.3719 (1.4); 7.3532 (3.0); 7.3211 (1.0); 7.3129 (1.2); 7.3075 (1.1); 7.2996 (1.7); 7.2926 (0.9); 7.2892 (0.8); 7.2801 (1.0); 7.2488 (0.4); 7.2454 (0.3); 7.2291 (2.6); 7.2254 (3.8); 7.2156 (4.6); 7.2136 (4.3); 7.2026 (0.6); 7.0876 (2.5); 7.0820 (2.5); 3.3249 (37.4); 3.1684 (0.4); 3.1512 (1.1); 3.1339 (1.6); 3.1167 (1.2); 3.0994 (0.5); 2.7870 (0.6); 2.7795 (0.9); 2.7702 (1.2); 2.7636 (1.2); 2.7544 (0.9); 2.7467 (0.6); 2.6798 (0.3); 2.6753 (0.7); 2.6708 (1.0); 2.6661 (0.7); 2.6617 (0.3); 2.5243 (3.0); 2.5196 (4.4); 2.5108 (57.1); 2.5064 (115.8); 2.5018 (151.1); 2.4972 (107.8); 2.4927 (51.5); 2.3332 (0.7); 2.3286 (0.9); 2.3240 (0.7); 2.0738 (0.6); 1.3012 (6.0); 1.2017 (15.9); 1.1845 (16.0); 1.1729 (2.3); 1.1536 (0.4); 0.7062 (0.7); 0.6882 (2.8); 0.6763 (2.7); 0.6702 (2.4); 0.6596 (1.0); 0.6212 (0.4); 0.5917 (1.1); 0.5818 (3.1); 0.5741 (3.0); 0.5676 (2.2); 0.5543 (0.7); 0.1459 (0.6); 0.0080 (4.6); −0.0002 (145.9); −0.0085 (5.1); −0.1496 (0.6) I-052 [00176]
I-052: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 11.8247 (2.7); 10.0205 (2.9); 8.1751 (4.3); 8.1416 (1.2); 8.0028 (1.8); 7.9813 (7.5); 7.9670 (5.8); 7.9455 (1.6); 7.7483 (0.4); 7.7401 (4.3); 7.7349 (1.5); 7.7233 (1.6); 7.7177 (5.8); 7.7096 (0.6); 7.5655 (3.3); 7.5441 (2.7); 7.3711 (1.3); 7.3522 (2.5); 7.3202 (0.8); 7.3120 (0.9); 7.3070 (0.9); 7.2988 (1.3); 7.2883 (0.7); 7.2791 (0.8); 7.2282 (2.2); 7.2242 (3.6); 7.2133 (3.8); 6.5824 (1.7); 6.5630 (1.7); 4.0517 (0.6); 4.0352 (1.0); 4.0167 (1.0); 4.0002 (0.7); 3.3256 (9.5); 3.1675 (0.4); 3.1504 (1.0); 3.1331 (1.3); 3.1158 (1.0); 3.0988 (0.4); 2.6707 (0.4); 2.5241 (1.1); 2.5106 (25.0); 2.5063 (50.0); 2.5019 (64.9); 2.4973 (46.7); 2.4930 (22.7); 2.3286 (0.4); 1.2438 (16.0); 1.2275 (15.9); 1.2008 (13.7); 1.1836 (13.5); 0.0079 (2.2); −0.0002 (59.6); −0.0085 (2.0) I-053 [00177]
I-053: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 8.3407 (11.6); 8.0185 (8.4); 7.9976 (10.7); 7.8131 (10.2); 7.7935 (16.0); 7.7768 (4.2); 7.7716 (11.8); 7.7638 (1.5); 7.5899 (7.7); 7.5686 (6.5); 7.5490 (4.4); 7.5334 (4.5); 7.5226 (2.2); 7.5189 (2.4); 7.5027 (5.3); 7.4992 (5.2); 7.4885 (3.0); 7.4859 (3.0); 7.4685 (3.8); 7.4514 (1.5); 7.4485 (1.5); 7.3554 (1.8); 7.3513 (1.8); 7.3356 (3.6); 7.3321 (3.4); 7.3183 (2.4); 7.3143 (2.3); 7.2728 (5.2); 7.2706 (5.3); 7.2536 (3.3); 7.2509 (3.0); 4.9478 (1.2); 4.9302 (2.6); 4.9136 (2.9); 4.8963 (2.0); 4.8806 (0.6); 4.8128 (6.0); 4.7965 (9.7); 4.7790 (5.0); 4.6284 (6.1); 4.6121 (11.2); 4.5965 (5.2); 4.2775 (4.0); 4.2341 (7.0); 4.1610 (7.4); 4.1176 (3.8); 3.3199 (70.4); 2.8219 (0.8); 2.8050 (2.0); 2.7879 (2.8); 2.7708 (2.1); 2.7537 (0.8); 2.6748 (0.6); 2.6704 (0.8); 2.6661 (0.6); 2.5059 (103.3); 2.5016 (130.8); 2.4972 (96.2); 2.3327 (0.6); 2.3284 (0.8); 2.3238 (0.6); 1.1676 (14.2); 1.1504 (15.7); 1.1429 (15.4); 1.1257 (13.7); −0.0001 (37.1) I-054 [00178]
I-054: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 10.7815 (1.7); 9.9727 (2.9); 7.9656 (0.5); 7.9613 (0.4); 7.9436 (0.6); 7.9121 (2.9); 7.8904 (4.1); 7.7850 (3.9); 7.7633 (3.4); 7.7493 (5.9); 7.7443 (2.3); 7.7324 (2.2); 7.7268 (7.1); 7.7188 (0.8); 7.6259 (0.5); 7.6039 (0.5); 7.5590 (5.4); 7.5364 (5.3); 7.5145 (2.4); 7.4837 (1.1); 7.4656 (1.7); 7.4468 (0.8); 7.3619 (0.8); 7.3587 (0.9); 7.3419 (1.7); 7.3244 (1.0); 7.3213 (1.0); 7.2730 (2.3); 7.2708 (2.3); 7.2535 (1.5); 4.2454 (1.6); 4.2004 (2.7); 4.1107 (3.1); 4.0657 (1.8); 3.3222 (54.4); 2.7535 (0.4); 2.7364 (1.2); 2.7193 (1.6); 2.7021 (1.2); 2.6849 (0.5); 2.6798 (0.5); 2.6751 (0.9); 2.6705 (1.3); 2.6660 (0.9); 2.6613 (0.4); 2.5241 (3.6); 2.5194 (5.2); 2.5107 (70.8); 2.5062 (145.6); 2.5016 (191.9); 2.4970 (136.2); 2.4924 (64.3); 2.3376 (0.4); 2.3330 (0.8); 2.3285 (1.2); 2.3238 (0.8); 2.3191 (0.4); 2.0741 (0.8); 2.0433 (1.9); 2.0276 (16.0); 1.1999 (5.3); 1.1829 (5.2); 1.1257 (8.2); 1.1086 (8.0); 0.1458 (0.4); 0.0080 (3.4); −0.0001 (114.4); −0.0085 (3.6); −0.1497 (0.4) I-055 [00179]
I-055: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 9.9089 (6.3); 8.3147 (1.1); 7.8896 (0.4); 7.8815 (0.6); 7.8593 (0.8); 7.8305 (6.0); 7.8088 (8.8); 7.7784 (1.1); 7.7590 (11.4); 7.7537 (4.4); 7.7419 (5.0); 7.7365 (14.4); 7.7228 (8.7); 7.7008 (5.9); 7.5584 (1.1); 7.5307 (12.8); 7.5085 (12.9); 7.4817 (2.3); 7.4640 (3.5); 7.4455 (1.6); 7.3591 (1.8); 7.3560 (1.8); 7.3393 (3.6); 7.3212 (2.2); 7.2684 (4.8); 7.2490 (3.2); 6.6488 (10.8); 4.2373 (3.3); 4.1923 (5.6); 4.1041 (6.2); 4.0590 (3.5); 3.3238 (574.2); 2.7506 (0.9); 2.7336 (2.3); 2.7166 (3.1); 2.6996 (2.4); 2.6798 (2.0); 2.6751 (3.0); 2.6705 (3.9); 2.6659 (2.8); 2.6616 (1.3); 2.5237 (18.1); 2.5105 (253.2); 2.5061 (482.2); 2.5015 (612.3); 2.4969 (429.2); 2.4924 (200.7); 2.3375 (1.4); 2.3328 (2.8); 2.3283 (3.7); 2.3238 (2.6); 2.3192 (1.2); 2.0271 (0.8); 1.2346 (0.6); 1.1971 (11.3); 1.1801 (10.9); 1.1241 (16.0); 1.1070 (15.6); 0.1457 (1.3); 0.0078 (13.6); −0.0003 (319.2); −0.0087 (10.6); −0.1498 (1.3) I-056 [00180]
I-056: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 8.3481 (12.9); 8.3156 (0.5); 8.1442 (2.8); 8.0107 (8.9); 7.9898 (11.8); 7.8123 (10.8); 7.7912 (8.9); 7.7778 (1.2); 7.7695 (11.0); 7.7640 (3.7); 7.7526 (4.1); 7.7469 (14.1); 7.7386 (1.5); 7.5555 (7.5); 7.5348 (6.3); 7.5238 (2.2); 7.5195 (2.3); 7.5037 (5.2); 7.4997 (5.1); 7.4890 (2.9); 7.4858 (2.9); 7.4714 (3.5); 7.4684 (3.8); 7.4519 (1.5); 7.4485 (1.5); 7.3561 (2.0); 7.3517 (2.0); 7.3364 (3.8); 7.3322 (3.6); 7.3190 (2.7); 7.3147 (2.7); 7.2765 (5.3); 7.2735 (5.3); 7.2570 (3.4); 7.2537 (3.0); 6.7325 (9.6); 4.2797 (4.8); 4.2364 (7.8); 4.1615 (8.3); 4.1182 (4.6); 3.3236 (40.7); 2.8226 (0.8); 2.8058 (2.1); 2.7887 (2.9); 2.7716 (2.1); 2.7545 (0.8); 2.6802 (0.5); 2.6755 (1.1); 2.6709 (1.6); 2.6663 (1.2); 2.6618 (0.5); 2.5244 (4.6); 2.5197 (7.2); 2.5110 (95.9); 2.5066 (197.2); 2.5020 (259.2); 2.4974 (184.0); 2.4928 (86.6); 2.3381 (0.5); 2.3334 (1.2); 2.3288 (1.6); 2.3242 (1.2); 2.3198 (0.5); 2.0741 (0.6); 1.1672 (14.9); 1.1500 (16.0); 1.1431 (15.9); 1.1259 (14.4); 1.1019 (0.5); 1.0847 (0.4); 0.1461 (0.4); 0.0081 (3.1); 0.0000 (94.7); −0.0084 (3.0); −0.1495 (0.4) I-057 [00181]
I-057: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 11.8297 (3.9); 10.0289 (3.6); 8.1753 (4.8); 8.0124 (2.0); 7.9907 (9.2); 7.9779 (7.2); 7.9562 (1.8); 7.7593 (0.5); 7.7511 (5.3); 7.7456 (1.9); 7.7342 (2.1); 7.7285 (7.2); 7.7204 (0.8); 7.5857 (4.0); 7.5650 (3.2); 7.5241 (2.2); 7.5036 (2.3); 7.3715 (1.5); 7.3529 (3.0); 7.3211 (1.0); 7.3137 (1.1); 7.3068 (1.2); 7.2997 (1.6); 7.2936 (0.7); 7.2883 (0.8); 7.2801 (0.9); 7.2480 (0.5); 7.2446 (0.4); 7.2283 (2.4); 7.2248 (3.1); 7.2207 (3.5); 7.2139 (4.6); 7.2120 (4.4); 7.2015 (0.5); 5.7551 (1.1); 5.1643 (0.7); 5.1423 (1.5); 5.1217 (1.5); 5.1003 (0.7); 3.6031 (2.1); 3.5803 (4.4); 3.5575 (2.4); 3.3321 (2.7); 3.3215 (28.1); 3.3120 (4.2); 3.2893 (2.0); 3.1668 (0.4); 3.1495 (1.1); 3.1324 (1.5); 3.1151 (1.2); 3.0980 (0.5); 2.6749 (0.5); 2.6705 (0.7); 2.6660 (0.5); 2.5240 (1.7); 2.5192 (2.8); 2.5105 (41.2); 2.5061 (84.0); 2.5016 (110.0); 2.4970 (79.2); 2.4925 (38.1); 2.3330 (0.5); 2.3285 (0.7); 2.3239 (0.5); 2.0738 (1.5); 1.3015 (0.4); 1.2005 (16.0); 1.1832 (15.8); 0.1459 (0.5); 0.0080 (5.1); −0.0002 (137.3); −0.0085 (5.1); −0.1495 (0.5) I-058 [00182]
I-058: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 8.7823 (0.4); 8.3438 (12.9); 8.3130 (2.5); 8.1153 (0.4); 8.0538 (9.1); 8.0329 (11.7); 7.9964 (0.4); 7.8209 (10.7); 7.7999 (9.2); 7.7526 (1.0); 7.7399 (0.4); 7.7256 (1.1); 7.7173 (10.6); 7.7119 (3.8); 7.7004 (3.9); 7.6948 (13.8); 7.6867 (1.5); 7.6763 (0.3); 7.5387 (8.2); 7.5184 (7.7); 7.5046 (5.6); 7.5007 (5.6); 7.4905 (3.0); 7.4874 (3.1); 7.4726 (3.6); 7.4700 (4.0); 7.4533 (1.5); 7.4502 (1.6); 7.3576 (1.9); 7.3533 (1.9); 7.3380 (3.8); 7.3338 (3.8); 7.3205 (2.6); 7.3163 (2.6); 7.2757 (5.4); 7.2730 (5.7); 7.2563 (3.4); 7.2533 (3.2); 7.0921 (4.8); 7.0866 (5.0); 4.3458 (0.3); 4.2770 (4.6); 4.2336 (7.8); 4.1623 (8.3); 4.1190 (4.4); 3.3261 (246.4); 3.3024 (1.5); 2.8240 (0.8); 2.8068 (2.2); 2.7895 (3.6); 2.7776 (2.4); 2.7719 (3.9); 2.7623 (2.7); 2.7539 (2.4); 2.7456 (1.2); 2.7365 (0.7); 2.6753 (0.6); 2.6709 (0.8); 2.6664 (0.6); 2.5244 (2.2); 2.5197 (3.3); 2.5109 (48.8); 2.5065 (102.6); 2.5020 (137.4); 2.4974 (99.8); 2.4930 (48.6); 2.3332 (0.6); 2.3288 (0.8); 2.3242 (0.6); 1.1976 (0.3); 1.1707 (15.5); 1.1536 (16.0); 1.1440 (15.7); 1.1269 (14.7); 1.1041 (0.6); 1.0866 (0.4); 1.0747 (0.7); 1.0572 (1.2); 1.0397 (0.6); 0.7044 (1.5); 0.6862 (5.8); 0.6744 (5.4); 0.6685 (5.0); 0.6579 (2.1); 0.6363 (0.4); 0.6305 (0.4); 0.6204 (0.8); 0.5916 (2.4); 0.5816 (6.4); 0.5735 (6.2); 0.5676 (4.5); 0.5541 (1.4); 0.1458 (0.4); 0.0081 (3.1); −0.0001 (99.9); −0.0084 (3.6); −0.1498 (0.4) I-059 [00183]
I-059: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 8.3403 (7.2); 8.0349 (5.1); 8.0140 (6.6); 7.8155 (6.0); 7.7944 (5.1); 7.7390 (0.8); 7.7307 (5.7); 7.7254 (2.1); 7.7138 (2.4); 7.7082 (7.8); 7.7002 (0.8); 7.5767 (4.8); 7.5559 (3.6); 7.5250 (1.0); 7.5210 (1.3); 7.5054 (3.0); 7.5015 (3.1); 7.4917 (1.7); 7.4888 (1.8); 7.4740 (2.0); 7.4713 (2.2); 7.4545 (0.8); 7.4514 (0.9); 7.3581 (1.1); 7.3538 (1.1); 7.3385 (2.1); 7.3344 (2.1); 7.3210 (1.4); 7.3168 (1.5); 7.2745 (3.1); 7.2718 (3.2); 7.2551 (2.0); 7.2521 (1.8); 6.8466 (1.1); 6.8330 (2.3); 6.8192 (1.1); 4.2758 (2.6); 4.2324 (4.3); 4.1619 (4.6); 4.1185 (2.4); 3.5967 (1.6); 3.5813 (5.2); 3.5675 (3.9); 3.5232 (1.8); 3.5098 (3.6); 3.5008 (3.7); 3.4957 (3.1); 3.4834 (8.3); 3.4730 (1.1); 3.4659 (7.9); 3.4577 (0.8); 3.4485 (2.8); 3.4399 (0.7); 3.4273 (0.8); 3.3649 (866.0); 2.8218 (0.5); 2.8049 (1.2); 2.7877 (1.7); 2.7706 (1.3); 2.7537 (0.5); 2.6780 (0.6); 2.6735 (0.8); 2.6689 (0.6); 2.5267 (2.9); 2.5133 (47.7); 2.5090 (96.3); 2.5045 (126.9); 2.4999 (91.8); 2.4956 (44.4); 2.3358 (0.5); 2.3313 (0.8); 2.3266 (0.6); 2.0951 (0.4); 1.1692 (8.6); 1.1521 (9.2); 1.1432 (9.0); 1.1237 (12.3); 1.1140 (1.4); 1.1060 (16.0); 1.0885 (7.6); 1.0749 (0.5); 1.0575 (0.8); 1.0400 (0.4); 0.1458 (0.4); 0.0079 (3.8); −0.0002 (96.4); −0.0085 (3.4); −0.1497 (0.4) I-060 [00184]
I-060: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 11.8275 (4.1); 10.0264 (3.8); 8.1767 (5.0); 8.0057 (1.8); 7.9841 (9.7); 7.9736 (7.7); 7.9518 (1.7); 7.7421 (0.5); 7.7339 (5.2); 7.7286 (1.9); 7.7169 (2.0); 7.7114 (7.0); 7.7033 (0.8); 7.5750 (4.1); 7.5541 (3.3); 7.3713 (1.5); 7.3526 (3.1); 7.3209 (1.0); 7.3133 (1.1); 7.3068 (1.2); 7.2996 (1.6); 7.2931 (0.8); 7.2885 (0.8); 7.2800 (1.0); 7.2481 (0.4); 7.2451 (0.4); 7.2284 (2.5); 7.2249 (3.3); 7.2217 (3.7); 7.2143 (4.6); 7.2024 (0.5); 6.8422 (1.0); 6.8283 (2.2); 6.8145 (1.1); 3.6003 (1.4); 3.5849 (4.7); 3.5710 (3.4); 3.5264 (1.5); 3.5131 (3.1); 3.5028 (3.4); 3.4994 (2.7); 3.4854 (7.4); 3.4680 (6.9); 3.4505 (2.2); 3.3251 (21.5); 3.1690 (0.4); 3.1518 (1.1); 3.1346 (1.5); 3.1174 (1.1); 3.1000 (0.4); 2.6711 (0.3); 2.5245 (0.9); 2.5197 (1.4); 2.5110 (19.4); 2.5066 (40.0); 2.5021 (53.2); 2.4976 (39.0); 2.4933 (19.4); 1.2014 (16.0); 1.1842 (15.8); 1.1520 (0.4); 1.1549 (0.5); 1.1249 (7.0); 1.1075 (14.2); 1.0900 (6.8); 1.0704 (0.7); 0.0079 (1.3); −0.0002 (39.0); −0.0084 (1.5) I-061 [00185]
I-061: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 11.8315 (3.4); 10.0324 (3.1); 9.7539 (0.4); 8.6621 (4.6); 8.2209 (0.6); 8.2125 (5.2); 8.2071 (1.8); 8.1896 (9.8); 8.0809 (3.4); 8.0598 (6.0); 8.0011 (4.6); 7.9800 (2.8); 7.5264 (3.4); 7.5053 (3.2); 7.3763 (1.3); 7.3574 (2.6); 7.3249 (0.8); 7.3167 (1.0); 7.3115 (1.0); 7.3036 (1.4); 7.2960 (0.7); 7.2933 (0.8); 7.2840 (0.9); 7.2523 (0.4); 7.2325 (2.4); 7.2282 (3.6); 7.2191 (4.0); 7.2173 (3.9); 7.2082 (0.4); 6.8299 (0.5); 6.8073 (0.5); 3.5684 (2.7); 3.3249 (14.9); 3.2030 (16.0); 3.1737 (0.4); 3.1569 (1.0); 3.1399 (1.4); 3.1226 (1.0); 3.1052 (0.4); 3.0770 (14.9); 2.6753 (0.6); 2.6707 (0.8); 2.6662 (0.6); 2.5241 (2.2); 2.5106 (49.3); 2.5062 (99.8); 2.5017 (130.8); 2.4972 (94.2); 2.4928 (45.7); 2.3331 (0.6); 2.3286 (0.8); 2.3240 (0.6); 2.2817 (0.4); 1.2328 (1.0); 1.2066 (14.2); 1.1894 (14.0); 0.1461 (0.4); 0.0080 (3.2); −0.0001 (88.5); −0.0084 (3.3); −0.1496 (0.4) I-062 [00186]
I-062: .sup.1H-NMR(400.00 MHz, d.sub.6-DMSO): δ = 8.6514 (4.6); 8.3581 (5.6); 8.2151 (1.1); 8.2067 (5.4); 8.2013 (2.2); 8.1894 (2.1); 8.1838 (5.7); 8.1755 (0.7); 8.1099 (4.5); 8.0890 (5.1); 7.8425 (5.0); 7.8215 (4.2); 7.5308 (4.2); 7.5081 (5.6); 7.4930 (1.6); 7.4900 (1.6); 7.4753 (1.8); 7.4726 (1.8); 7.4559 (0.7); 7.4527 (0.7); 7.3604 (1.1); 7.3561 (1.0); 7.3407 (1.9); 7.3366 (1.7); 7.3232 (1.3); 7.3191 (1.2); 7.2805 (2.6); 7.2778 (2.5); 7.2610 (1.6); 7.2580 (1.4); 4.2846 (2.0); 4.2414 (3.4); 4.1678 (3.6); 4.1245 (1.9); 3.3246 (25.3); 3.2017 (16.0); 3.0747 (14.7); 2.8262 (0.5); 2.8090 (1.1); 2.7919 (1.4); 2.7746 (1.0); 2.7574 (0.4); 2.6759 (0.4); 2.6713 (0.4); 2.6673 (0.3); 2.5115 (34.6); 2.5071 (58.2); 2.5026 (71.0); 2.4981 (49.4); 2.4937 (23.1); 2.3521 (0.4); 2.3340 (0.3); 2.3295 (0.4); 1.2313 (0.5); 1.2109 (0.5); 1.1721 (7.5); 1.1549 (8.0); 1.1463 (7.6); 1.1291 (6.6); 1.0748 (0.5); 1.0573 (0.8); 1.0398 (0.4); 0.0179 (1.3); 0.0080 (2.6); −0.0001 (32.2); −0.0085 (1.2) I-063 [00187]
I-063: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 10.0574 (1.4); 8.0913 (0.4); 8.0833 (3.0); 8.0659 (1.2); 8.0604 (3.5); 8.0522 (0.4); 7.9588 (1.4); 7.9376 (1.8); 7.8228 (1.8); 7.8010 (1.4); 7.5463 (2.7); 7.5237 (2.8); 7.4886 (0.6); 7.4706 (0.9); 7.4511 (0.4); 7.3624 (0.5); 7.3453 (1.0); 7.3258 (0.6); 7.2723 (1.4); 7.2529 (0.9); 5.7552 (0.8); 4.2619 (0.9); 4.2168 (1.6); 4.1233 (1.9); 4.0783 (1.1); 4.0561 (1.2); 4.0383 (3.6); 4.0205 (3.6); 4.0027 (1.2); 3.3494 (0.8); 2.7355 (0.6); 2.7183 (0.9); 2.7012 (0.6); 2.6714 (0.3); 2.5246 (1.1); 2.5112 (20.6); 2.5070 (41.5); 2.5025 (54.6); 2.4980 (40.1); 2.4937 (19.9); 2.3294 (0.3); 1.9889 (16.0); 1.2322 (0.8); 1.1933 (5.9); 1.1801 (3.1); 1.1755 (9.6); 1.1577 (4.3); 1.1283 (4.5); 1.1112 (4.4); 0.0079 (1.0); −0.0002 (26.2); −0.0084 (1.1) I-064 [00188]
I-064: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 8.3453 (11.0); 8.3155 (0.5); 8.0513 (8.4); 8.0308 (10.2); 7.8161 (9.8); 7.7954 (8.5); 7.7560 (8.6); 7.7338 (10.7); 7.5626 (9.2); 7.5407 (7.8); 7.5212 (2.6); 7.5019 (5.8); 7.4889 (3.4); 7.4703 (4.2); 7.4515 (1.7); 7.3535 (1.9); 7.3364 (4.0); 7.3193 (2.5); 7.3166 (2.5); 7.2753 (5.7); 7.2565 (3.4); 6.7824 (3.4); 6.7710 (3.4); 4.2781 (3.6); 4.2348 (6.7); 4.1617 (7.0); 4.1184 (3.5); 3.3223 (33.4); 2.9313 (15.7); 2.9199 (16.0); 2.8225 (0.9); 2.8058 (2.1); 2.7889 (2.9); 2.7716 (2.2); 2.7549 (1.0); 2.6707 (1.1); 2.5017 (179.4); 2.3285 (1.1); 1.1695 (14.2); 1.1522 (15.8); 1.1436 (15.8); 1.1264 (13.8); −0.0003 (4.6) I-065 [00189]
I-065: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 8.3479 (12.2); 8.3148 (0.6); 8.2260 (15.2); 8.0132 (8.8); 7.9923 (11.5); 7.8125 (10.5); 7.7913 (9.4); 7.7815 (10.6); 7.7763 (3.8); 7.7645 (3.9); 7.7591 (13.1); 7.7510 (1.5); 7.7378 (0.5); 7.7154 (0.4); 7.5521 (9.2); 7.5299 (8.0); 7.5234 (2.9); 7.5195 (3.0); 7.5034 (5.2); 7.4996 (5.2); 7.4886 (2.9); 7.4858 (2.9); 7.4683 (3.9); 7.4516 (1.5); 7.4485 (1.5); 7.3559 (1.8); 7.3516 (1.8); 7.3361 (3.6); 7.3323 (3.5); 7.3187 (2.5); 7.3146 (2.5); 7.2758 (5.3); 7.2731 (5.3); 7.2564 (3.3); 7.2534 (3.0); 6.7449 (9.3); 4.2791 (4.3); 4.2357 (7.3); 4.1613 (7.8); 4.1180 (4.2); 3.6584 (0.3); 3.3823 (1.0); 3.3402 (1.1); 3.1351 (0.4); 2.8228 (0.9); 2.8059 (2.2); 2.7888 (3.0); 2.7717 (2.2); 2.7547 (0.8); 2.6750 (1.6); 2.6706 (2.3); 2.6661 (1.7); 2.5238 (7.2); 2.5103 (141.0); 2.5061 (285.0); 2.5016 (374.7); 2.4971 (271.4); 2.4927 (133.4); 2.3328 (1.7); 2.3284 (2.3); 2.3239 (1.7); 1.1673 (14.8); 1.1502 (16.0); 1.1432 (16.0); 1.1260 (14.4); 1.1083 (0.8); 1.0899 (0.4); 0.0078 (0.5); −0.0002 (14.4); −0.0084 (0.6) I-066 [00190]
I-066: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 11.8137 (2.9); 10.0418 (2.7); 8.7752 (0.4); 8.1741 (3.7); 8.0708 (0.4); 7.9853 (1.0); 7.9698 (16.0); 7.8053 (0.5); 7.7997 (0.5); 7.7847 (3.8); 7.7625 (4.2); 7.5507 (3.7); 7.5289 (3.0); 7.3715 (1.1); 7.3531 (2.1); 7.3172 (0.8); 7.3013 (1.3); 7.2854 (0.6); 7.2812 (0.7); 7.2428 (0.5); 7.2241 (1.6); 7.2060 (3.3); 7.1868 (0.6); 6.7703 (0.5); 6.7309 (3.9); 3.3242 (23.8); 3.1537 (0.8); 3.1362 (1.1); 3.1190 (0.8); 3.1024 (0.3); 2.6712 (0.5); 2.5022 (80.1); 2.3285 (0.5); 2.0743 (0.5); 1.2000 (10.8); 1.1829 (10.7); −0.0002 (9.5) I-067 [00191]
I-067: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 11.8253 (4.3); 10.0296 (3.9); 8.1805 (5.0); 8.0224 (3.0); 8.0014 (7.8); 7.9751 (6.4); 7.9540 (2.7); 7.7669 (0.6); 7.7588 (5.1); 7.7365 (6.4); 7.7288 (0.8); 7.5605 (5.1); 7.5384 (4.3); 7.3723 (1.6); 7.3534 (3.2); 7.3213 (1.0); 7.3134 (1.2); 7.3075 (1.2); 7.3001 (1.7); 7.2931 (0.8); 7.2892 (0.8); 7.2804 (0.9); 7.2486 (0.4); 7.2235 (3.9); 7.2144 (5.0); 7.2031 (0.6); 6.7848 (0.6); 6.7737 (1.8); 6.7620 (1.9); 6.7512 (0.6); 4.1139 (0.4); 4.1007 (1.1); 4.0877 (1.1); 4.0749 (0.4); 3.3267 (17.9); 3.1771 (5.1); 3.1642 (5.0); 3.1536 (1.2); 3.1363 (1.6); 3.1193 (1.2); 3.1023 (0.5); 2.9349 (8.9); 2.9234 (8.8); 2.5064 (42.6); 2.5023 (54.7); 2.4981 (40.4); 1.3015 (0.9); 1.2027 (16.0); 1.1855 (15.7); −0.0002 (8.0) I-068 [00192]
I-068: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 11.8289 (3.9); 10.0213 (3.6); 8.1766 (4.9); 8.0110 (2.1); 7.9894 (9.1); 7.9760 (7.2); 7.9543 (1.9); 7.7689 (0.5); 7.7606 (5.4); 7.7552 (2.0); 7.7437 (2.0); 7.7381 (6.9); 7.7299 (0.7); 7.5651 (4.1); 7.5442 (3.4); 7.3715 (1.5); 7.3526 (3.0); 7.3206 (1.0); 7.3124 (1.1); 7.3073 (1.1); 7.2993 (1.6); 7.2890 (0.8); 7.2797 (0.9); 7.2486 (0.4); 7.2288 (2.6); 7.2247 (4.2); 7.2154 (4.4); 7.2137 (4.4); 7.2047 (0.4); 6.9432 (2.2); 6.9286 (2.2); 4.4282 (0.5); 4.4134 (1.0); 4.4098 (0.9); 4.3983 (0.9); 4.3949 (1.0); 4.3824 (0.6); 3.9723 (1.7); 3.9568 (1.9); 3.9499 (2.2); 3.9345 (1.8); 3.8756 (0.7); 3.8562 (1.7); 3.8376 (2.0); 3.8192 (1.0); 3.7541 (1.0); 3.7394 (1.2); 3.7341 (1.8); 3.7193 (1.8); 3.7140 (0.9); 3.6990 (0.8); 3.6792 (1.8); 3.6678 (1.8); 3.6568 (1.6); 3.6455 (1.6); 3.3220 (21.9); 3.1681 (0.4); 3.1507 (1.1); 3.1334 (1.5); 3.1162 (1.1); 3.0991 (0.4); 2.8901 (0.5); 2.7311 (0.4); 2.6707 (0.4); 2.5241 (1.0); 2.5106 (24.5); 2.5062 (50.4); 2.5017 (66.2); 2.4972 (47.6); 2.4928 (23.1); 2.3285 (0.4); 2.2601 (0.4); 2.2408 (0.9); 2.2282 (0.7); 2.2235 (1.0); 2.2090 (1.2); 2.1916 (1.1); 2.1726 (0.4); 2.0140 (0.5); 1.9999 (0.7); 1.9952 (0.7); 1.9881 (0.8); 1.9824 (1.1); 1.9687 (1.0); 1.9561 (0.5); 1.9512 (0.5); 1.9374 (0.4); 1.2011 (16.0); 1.1839 (15.8); 1.1624 (0.4); −0.0002 (7.0) I-069 [00193]
I-069: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 8.3417 (12.8); 8.3119 (0.5); 8.0411 (9.1); 8.0201 (11.8); 7.8177 (10.8); 7.7966 (9.0); 7.7662 (1.1); 7.7580 (10.8); 7.7525 (3.8); 7.7410 (4.5); 7.7354 (14.1); 7.7273 (1.5); 7.7154 (0.3); 7.5648 (7.7); 7.5442 (6.5); 7.5231 (1.8); 7.5191 (2.2); 7.5034 (5.3); 7.4994 (5.2); 7.4893 (3.0); 7.4861 (3.0); 7.4716 (3.6); 7.4688 (3.9); 7.4522 (1.5); 7.4489 (1.6); 7.3561 (2.0); 7.3517 (2.0); 7.3364 (3.9); 7.3322 (3.6); 7.3189 (2.7); 7.3147 (2.7); 7.2734 (5.4); 7.2705 (5.4); 7.2539 (3.5); 7.2508 (3.2); 6.9451 (4.2); 6.9304 (4.4); 5.7516 (3.3); 4.4356 (0.4); 4.4235 (1.0); 4.4208 (1.0); 4.4088 (1.8); 4.4055 (1.7); 4.3936 (1.7); 4.3898 (1.8); 4.3778 (1.0); 4.3750 (1.1); 4.3631 (0.4); 4.2761 (4.7); 4.2327 (7.8); 4.1608 (8.4); 4.1174 (4.6); 4.0564 (0.8); 4.0386 (2.3); 4.0208 (2.3); 4.0030 (0.8); 3.9709 (3.3); 3.9553 (3.6); 3.9485 (4.3); 3.9330 (3.5); 3.8745 (1.3); 3.8551 (3.1); 3.8363 (3.7); 3.8180 (1.9); 3.7539 (2.0); 3.7392 (2.4); 3.7340 (3.5); 3.7192 (3.6); 3.7137 (1.8); 3.6989 (1.6); 3.6754 (3.6); 3.6641 (3.6); 3.6530 (3.2); 3.6418 (3.1); 3.3153 (123.0); 2.8240 (0.8); 2.8071 (2.1); 2.7900 (2.9); 2.7729 (2.2); 2.7558 (0.8); 2.6793 (0.4); 2.6747 (0.8); 2.6701 (1.1); 2.6656 (0.8); 2.6612 (0.4); 2.5237 (2.9); 2.5190 (4.5); 2.5103 (68.6); 2.5058 (141.8); 2.5012 (187.6); 2.4966 (132.8); 2.4921 (62.9); 2.3371 (0.4); 2.3326 (0.8); 2.3280 (1.1); 2.3234 (0.8); 2.3188 (0.4); 2.2593 (0.7); 2.2399 (1.8); 2.2274 (1.3); 2.2228 (1.8); 2.2083 (2.3); 2.2037 (1.2); 2.1911 (2.1); 2.1717 (0.8); 2.0105 (1.7); 1.9987 (1.6); 1.9880 (11.1); 1.9804 (2.2); 1.9663 (1.9); 1.9537 (1.0); 1.9494 (1.0); 1.9350 (0.7); 1.2336 (0.4); 1.1931 (3.0); 1.1753 (8.2); 1.1698 (15.3); 1.1573 (6.7); 1.1526 (16.0); 1.1438 (15.8); 1.1267 (14.7); 1.0985 (0.5); 1.0812 (0.4); 0.8886 (1.1); 0.8718 (1.1); 0.0080 (0.3); −0.0002 (11.7); −0.0085 (0.4) I-070 [00194]
I-070: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 11.7995 (4.2); 9.9706 (3.8); 8.1705 (5.1); 8.0149 (3.1); 7.9935 (8.2); 7.9676 (6.6); 7.9464 (2.7); 7.7539 (0.6); 7.7458 (5.5); 7.7405 (2.0); 7.7288 (2.3); 7.7233 (7.1); 7.7152 (0.8); 7.5645 (4.4); 7.5438 (3.5); 7.2441 (2.7); 7.2243 (3.7); 7.1197 (2.1); 7.1002 (1.6); 7.0223 (3.6); 6.7654 (0.6); 6.7546 (1.9); 6.7428 (1.9); 6.7318 (0.6); 3.3256 (53.5); 3.1140 (0.4); 3.0971 (1.1); 3.0798 (1.5); 3.0627 (1.1); 3.0451 (0.4); 2.9283 (9.4); 2.9167 (9.4); 2.6753 (0.5); 2.6708 (0.7); 2.6662 (0.5); 2.5241 (2.0); 2.5103 (43.8); 2.5063 (84.4); 2.5018 (108.8); 2.4973 (80.6); 2.4930 (40.2); 2.3329 (0.5); 2.3287 (0.7); 2.3243 (0.6); 2.2898 (15.5); 2.0744 (9.3); 1.1764 (16.0); 1.1592 (15.8); 0.0079 (2.4); −0.0002 (64.7); −0.0085 (2.6) I-071 [00195]
I-071: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 11.8283 (4.1); 10.0256 (3.7); 8.1735 (5.0); 8.0002 (1.7); 7.9785 (9.9); 7.9693 (8.0); 7.9473 (1.6); 7.7658 (0.6); 7.7575 (5.4); 7.7520 (2.1); 7.7406 (2.0); 7.7350 (6.9); 7.7269 (0.8); 7.5733 (4.0); 7.5525 (3.3); 7.3709 (1.5); 7.3523 (3.1); 7.3205 (1.0); 7.3132 (1.1); 7.3062 (1.2); 7.2992 (1.6); 7.2930 (0.8); 7.2876 (0.8); 7.2795 (1.0); 7.2476 (0.4); 7.2442 (0.4); 7.2278 (2.4); 7.2244 (3.1); 7.2203 (3.6); 7.2134 (4.6); 7.2117 (4.6); 7.2009 (0.6); 7.0561 (1.1); 7.0419 (2.3); 7.0273 (1.1); 6.0278 (0.5); 6.0144 (1.0); 6.0017 (0.9); 5.9887 (1.2); 5.9851 (0.7); 5.9752 (0.6); 5.9715 (1.2); 5.9586 (1.0); 5.9458 (1.2); 5.9324 (0.6); 5.7560 (0.6); 5.2712 (0.7); 5.2672 (1.9); 5.2628 (2.0); 5.2588 (0.8); 5.2283 (0.6); 5.2242 (1.7); 5.2198 (1.8); 5.2157 (0.8); 5.1209 (1.9); 5.1169 (1.9); 5.0953 (1.8); 5.0913 (1.8); 3.9955 (1.8); 3.9818 (3.2); 3.9681 (1.7); 3.3270 (27.6); 3.1667 (0.4); 3.1499 (1.1); 3.1329 (1.5); 3.1156 (1.2); 3.0985 (0.5); 2.6712 (0.4); 2.5245 (1.2); 2.5110 (24.4); 2.5066 (49.9); 2.5021 (66.3); 2.4975 (49.8); 2.4932 (25.5); 2.3288 (0.4); 2.0744 (1.0); 1.3012 (1.0); 1.2003 (16.0); 1.1831 (15.9); 0.0079 (0.8); −0.0002 (25.5); −0.0085 (1.1) I-072 [00196]
I-072: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 11.8319 (4.4); 10.0290 (4.0); 8.1776 (5.2); 8.0070 (2.0); 7.9854 (9.8); 7.9747 (7.9); 7.9532 (1.8); 7.7472 (0.4); 7.7403 (0.6); 7.7323 (5.2); 7.7270 (2.2); 7.7099 (6.7); 7.7020 (0.9); 7.5764 (4.5); 7.5550 (3.6); 7.3722 (1.6); 7.3531 (3.2); 7.3213 (1.0); 7.3136 (1.2); 7.3072 (1.3); 7.3001 (1.7); 7.2933 (0.8); 7.2888 (0.8); 7.2803 (0.9); 7.2485 (0.5); 7.2224 (4.0); 7.2148 (5.0); 7.2032 (0.6); 6.8611 (1.2); 6.8476 (2.2); 6.8352 (1.0); 3.5666 (1.5); 3.5533 (5.3); 3.5430 (5.9); 3.5266 (3.8); 3.5132 (2.4); 3.3297 (17.4); 3.2962 (2.2); 3.2846 (26.7); 3.1694 (0.4); 3.1523 (1.2); 3.1352 (1.6); 3.1180 (1.2); 3.1063 (0.4); 3.1010 (0.5); 2.5067 (33.9); 2.5025 (42.1); 2.4981 (31.1); 2.0748 (0.4); 1.3017 (0.9); 1.2017 (16.0); 1.1845 (15.8); −0.0002 (12.8) I-073 [00197]
I-073: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 11.8298 (2.2); 10.0265 (2.1); 8.1763 (2.8); 8.0070 (1.2); 7.9854 (5.1); 7.9720 (4.0); 7.9505 (1.0); 7.7445 (2.9); 7.7392 (1.1); 7.7276 (1.2); 7.7221 (3.9); 7.7141 (0.4); 7.5744 (2.3); 7.5535 (1.8); 7.3717 (0.8); 7.3530 (1.7); 7.3211 (0.6); 7.3134 (0.7); 7.3072 (0.6); 7.2998 (0.9); 7.2932 (0.4); 7.2887 (0.4); 7.2802 (0.5); 7.2289 (1.4); 7.2253 (1.9); 7.2225 (2.1); 7.2150 (2.6); 7.2028 (0.4); 6.8057 (0.6); 6.7920 (1.2); 6.7782 (0.6); 3.4412 (1.8); 3.4257 (4.5); 3.4103 (3.2); 3.3938 (1.5); 3.3768 (0.7); 3.3297 (16.8); 3.2506 (0.3); 3.2389 (16.0); 3.1515 (0.6); 3.1343 (0.9); 3.1171 (0.7); 2.5247 (0.5); 2.5112 (10.3); 2.5069 (20.1); 2.5024 (26.2); 2.4979 (19.2); 2.4936 (9.5); 1.8982 (0.4); 1.8822 (1.3); 1.8654 (1.9); 1.8487 (1.3); 1.8325 (0.4); 1.3014 (1.9); 1.2014 (8.8); 1.1842 (8.8); 0.0079 (0.3); 0.0002 (9.1); −0.0084 (0.3) I-074 [00198]
I-074: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 11.8289 (2.7); 10.0342 (2.5); 8.1748 (3.4); 8.0058 (0.8); 7.9997 (0.5); 7.9835 (9.3); 7.9578 (0.7); 7.7311 (0.4); 7.7227 (3.4); 7.7174 (1.3); 7.7058 (1.3); 7.7003 (4.8); 7.6924 (0.6); 7.5831 (2.8); 7.5620 (2.2); 7.3713 (1.0); 7.3530 (1.9); 7.3217 (0.7); 7.3157 (0.8); 7.3060 (0.9); 7.3005 (1.1); 7.2872 (0.5); 7.2807 (0.6); 7.2472 (0.4); 7.2437 (0.4); 7.2277 (1.4); 7.2243 (1.6); 7.2157 (2.3); 7.2096 (3.2); 7.1967 (0.4); 6.8928 (0.7); 6.8786 (1.4); 6.8640 (0.7); 4.8028 (1.0); 4.7891 (2.3); 4.7754 (1.0); 3.7133 (0.5); 3.6956 (1.8); 3.6893 (0.8); 3.6780 (1.9); 3.6716 (2.4); 3.6603 (0.8); 3.6540 (2.3); 3.6363 (0.7); 3.5535 (0.7); 3.5360 (2.2); 3.5296 (0.7); 3.5185 (2.4); 3.5120 (1.9); 3.5009 (0.8); 3.4944 (1.8); 3.4767 (0.5); 3.4245 (1.4); 3.4105 (2.4); 3.3964 (1.3); 3.3275 (23.1); 3.1511 (0.7); 3.1340 (1.0); 3.1168 (0.8); 2.5245 (0.9); 2.5112 (15.6); 2.5068 (31.4); 2.5023 (41.7); 2.4978 (31.1); 2.4934 (15.7); 1.2004 (10.6); 1.1832 (10.4); 1.1312 (7.9); 1.1136 (16.0); 1.0960 (7.6); 0.0080 (0.5); −0.0002 (15.2); −0.0083 (0.6) I-075 [00199]
I-075: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 11.8383 (4.0); 10.0175 (3.7); 8.1738 (4.9); 8.0029 (2.0); 7.9811 (9.6); 7.9695 (7.5); 7.9477 (1.7); 7.7661 (0.5); 7.7578 (5.6); 7.7523 (2.0); 7.7409 (2.1); 7.7352 (7.4); 7.7271 (0.8); 7.5730 (4.0); 7.5523 (3.3); 7.3719 (1.6); 7.3528 (3.0); 7.3208 (1.0); 7.3114 (1.4); 7.2994 (1.6); 7.2909 (1.2); 7.2797 (1.0); 7.2301 (3.2); 7.2271 (5.5); 7.2178 (4.5); 7.2159 (4.2); 6.7282 (2.1); 6.7095 (2.2); 4.0560 (0.5); 4.0383 (1.4); 4.0205 (1.4); 4.0027 (0.5); 3.9288 (0.4); 3.9019 (2.3); 3.8928 (2.0); 3.8738 (2.4); 3.4413 (1.5); 3.4164 (2.7); 3.4118 (2.7); 3.3874 (1.5); 3.3300 (31.4); 3.1662 (0.4); 3.1490 (1.1); 3.1319 (1.5); 3.1147 (1.2); 3.0975 (0.4); 2.5249 (0.8); 2.5203 (1.2); 2.5115 (16.2); 2.5070 (33.1); 2.5024 (43.6); 2.4978 (31.9); 2.4933 (15.5); 2.0113 (1.0); 1.9999 (0.4); 1.9891 (6.3); 1.9658 (1.4); 1.9606 (1.5); 1.9347 (1.7); 1.9295 (1.7); 1.6530 (0.6); 1.6420 (0.7); 1.6224 (1.3); 1.6130 (1.4); 1.5928 (1.3); 1.5842 (1.3); 1.5638 (0.6); 1.5529 (0.4); 1.2008 (16.0); 1.1934 (4.1); 1.1835 (15.8); 1.1755 (4.9); 1.1577 (1.9); 0.8885 (1.0); 0.8717 (1.0); 0.0080 (0.5); −0.0002 (18.3); −0.0085 (0.7) I-076 [00200]
I-076: .sup.1H-NMR(400 MHz, d.sub.6-DMSO): δ = 9.1049 (0.3); 8.5997 (0.3); 8.3439 (12.5); 8.1428 (0.4); 8.0551 (0.4); 8.0355 (9.0); 8.0146 (11.6); 7.9879 (0.3); 7.8812 (0.3); 7.8149 (10.6); 7.7939 (9.0); 7.7585 (0.4); 7.7363 (1.6); 7.7294 (10.2); 7.7240 (4.0); 7.7125 (4.2); 7.7069 (13.7); 7.6989 (1.6); 7.5770 (8.4); 7.5561 (6.5); 7.5240 (1.9); 7.5202 (2.4); 7.5043 (5.4); 7.5005 (5.5); 7.4898 (3.1); 7.4869 (3.1); 7.4720 (3.7); 7.4694 (4.0); 7.4527 (1.6); 7.4496 (1.6); 7.3569 (1.9); 7.3526 (1.9); 7.3372 (3.8); 7.3331 (3.7); 7.3198 (2.6); 7.3156 (2.6); 7.2759 (5.4); 7.2733 (5.6); 7.2565 (3.4); 7.2535 (3.2); 6.8697 (2.0); 6.8565 (4.0); 6.8440 (1.8); 4.2781 (4.4); 4.2347 (7.5); 4.1613 (8.0); 4.1281 (0.5); 4.1180 (4.3); 3.5703 (1.6); 3.5629 (2.6); 3.5587 (2.5); 3.5498 (10.2); 3.5394 (10.1); 3.5218 (6.7); 3.5084 (4.3); 3.4564 (0.5); 3.3288 (127.9); 3.2976 (2.4); 3.2829 (58.8); 3.2615 (0.4); 2.8233 (0.8); 2.8063 (2.2); 2.7892 (3.0); 2.7721 (2.2); 2.7551 (0.9); 2.6756 (0.6); 2.6712 (0.9); 2.6668 (0.6); 2.5245 (2.9); 2.5111 (52.6); 2.5067 (104.2); 2.5022 (137.0); 2.4977 (102.2); 2.4934 (51.7); 2.3336 (0.6); 2.3291 (0.9); 2.3245 (0.6); 1.3001 (0.5); 1.2094 (0.3); 1.1694 (15.0); 1.1523 (16.0); 1.1433 (15.8); 1.1262 (14.4); 1.0742 (0.5); 1.0567 (0.8); 1.0392 (0.4); 0.0079 (1.8); −0.0002 (49.4); −0.0084 (2.0) I-077 [00201]
I-077: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 8.3433 (3.8); 8.0378 (2.7); 8.0169 (3.5); 7.8148 (3.2); 7.7938 (2.8); 7.7512 (0.4); 7.7431 (3.2); 7.7381 (1.3); 7.7262 (1.4); 7.7207 (4.0); 7.7126 (0.5); 7.5758 (2.5); 7.5548 (2.0); 7.5237 (0.6); 7.5198 (0.7); 7.5040 (1.7); 7.5002 (1.7); 7.4896 (1.0); 7.4866 (1.0); 7.4692 (1.2); 7.4525 (0.5); 7.4493 (0.5); 7.3570 (0.6); 7.3527 (0.6); 7.3373 (1.2); 7.3334 (1.1); 7.3199 (0.8); 7.3158 (0.8); 7.2769 (1.7); 7.2742 (1.7); 7.2575 (1.0); 7.2545 (1.0); 6.8143 (0.6); 6.8008 (1.3); 6.7872 (0.6); 4.2782 (1.3); 4.2348 (2.3); 4.1618 (2.4); 4.1184 (1.3); 3.4394 (2.0); 3.4239 (4.8); 3.4084 (3.4); 3.3919 (1.6); 3.3749 (0.8); 3.3298 (14.0); 3.2388 (16.0); 2.8073 (0.7); 2.7902 (0.9); 2.7731 (0.7); 2.5246 (0.5); 2.5112 (9.5); 2.5069 (18.3); 2.5025 (23.8); 2.4980 (17.8); 2.4937 (9.1); 1.8970 (0.4); 1.8809 (1.4); 1.8640 (2.0); 1.8475 (1.4); 1.8313 (0.4); 1.3001 (0.9); 1.1699 (4.5); 1.1527 (4.9); 1.1437 (4.9); 1.1266 (4.4); 0.0077 (0.3); −0.0002 (8.1); −0.0085 (0.3) I-078 [00202]
I-078: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 11.8312 (4.1); 10.0278 (3.8); 8.1782 (5.0); 8.0045 (1.8); 7.9827 (10.4); 7.9736 (8.1); 7.9516 (1.6); 7.7736 (0.6); 7.7653 (5.6); 7.7599 (2.0); 7.7484 (2.1); 7.7429 (7.2); 7.7347 (0.8); 7.5725 (4.1); 7.5517 (3.4); 7.3721 (1.5); 7.3533 (3.1); 7.3214 (1.0); 7.3137 (1.2); 7.3076 (1.2); 7.3001 (1.6); 7.2934 (0.8); 7.2892 (0.8); 7.2805 (1.0); 7.2492 (0.4); 7.2459 (0.4); 7.2295 (2.6); 7.2259 (3.6); 7.2232 (3.8); 7.2156 (4.6); 7.2138 (4.5); 7.2039 (0.5); 6.7604 (1.1); 6.7466 (2.3); 6.7327 (1.1); 4.7672 (1.9); 4.7530 (4.4); 4.7388 (1.9); 3.6338 (1.2); 3.6184 (3.8); 3.6037 (4.3); 3.5890 (1.7); 3.4489 (1.3); 3.4345 (3.3); 3.4199 (3.0); 3.4047 (1.0); 3.3319 (23.6); 3.1775 (0.6); 3.1687 (0.4); 3.1644 (0.7); 3.1518 (1.1); 3.1347 (1.6); 3.1175 (1.2); 3.1005 (0.4); 2.5248 (0.6); 2.5199 (1.0); 2.5114 (13.9); 2.5069 (27.9); 2.5024 (36.5); 2.4978 (26.8); 2.4934 (13.2); 1.9890 (0.8); 1.2280 (0.3); 1.2018 (16.0); 1.1846 (15.8); 1.1574 (0.4); 0.0079 (0.4); −0.0002 (13.2); −0.0085 (0.4) I-079 [00203]
I-079: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 9.9268 (3.4); 7.8695 (3.2); 7.8477 (4.5); 7.7520 (0.3); 7.7325 (10.1); 7.7154 (3.7); 7.7100 (10.8); 7.5421 (5.0); 7.5199 (4.1); 7.4033 (2.5); 7.3832 (3.5); 7.2806 (1.8); 7.2607 (1.3); 7.0589 (3.3); 6.7091 (0.6); 6.6980 (1.8); 6.6863 (1.8); 6.6751 (0.6); 5.7560 (4.2); 4.2283 (1.8); 4.1833 (3.0); 4.0985 (3.5); 4.0535 (2.0); 3.3284 (84.9); 2.9295 (0.4); 2.9117 (10.3); 2.9001 (10.3); 2.6965 (0.4); 2.6798 (1.2); 2.6709 (0.8); 2.6630 (1.7); 2.6457 (1.2); 2.6287 (0.4); 2.5244 (1.4); 2.5196 (2.2); 2.5109 (30.1); 2.5065 (61.1); 2.5019 (80.3); 2.4973 (58.7); 2.4929 (28.7); 2.3333 (0.5); 2.3285 (0.8); 2.3145 (16.0); 2.0744 (1.1); 1.1727 (5.6); 1.1556 (5.5); 1.0997 (7.8); 1.0826 (7.7); 0.0080 (0.8); −0.0002 (28.0); −0.0086 (1.0) I-080 [00204]
I-080: .sup.1H-NMR(400 MHz, d.sub.6-DMSO): δ = 9.9082 (5.6); 8.8827 (0.6); 7.9061 (1.2); 7.8844 (1.5); 7.8524 (5.6); 7.8306 (8.0); 7.7271 (7.9); 7.7051 (16.0); 7.6883 (4.2); 7.6826 (14.1); 7.6747 (1.6); 7.5650 (3.3); 7.5566 (8.1); 7.5425 (3.5); 7.5340 (7.0); 7.5118 (4.6); 7.5090 (4.6); 7.4818 (2.1); 7.4641 (3.2); 7.4461 (1.4); 7.3595 (1.6); 7.3562 (1.7); 7.3400 (3.3); 7.3373 (3.2); 7.3220 (2.0); 7.3189 (1.9); 7.2671 (4.3); 7.2649 (4.4); 7.2477 (2.9); 6.7743 (2.1); 6.7605 (3.6); 6.7478 (1.7); 5.7561 (3.0); 4.2404 (3.1); 4.1954 (5.2); 4.1068 (5.9); 4.0617 (3.3); 3.5562 (2.8); 3.5510 (2.5); 3.5441 (3.3); 3.5372 (9.6); 3.5258 (8.7); 3.5127 (4.5); 3.5015 (6.7); 3.4880 (4.3); 3.4744 (1.1); 3.4693 (0.9); 3.3285 (115.1); 3.3014 (0.5); 3.2900 (8.8); 3.2760 (45.7); 2.7510 (0.8); 2.7340 (2.1); 2.7170 (2.9); 2.6998 (2.2); 2.6825 (0.9); 2.6752 (0.8); 2.6706 (1.0); 2.6661 (0.8); 2.5240 (2.5); 2.5192 (4.0); 2.5106 (50.7); 2.5062 (102.7); 2.5016 (136.0); 2.4971 (100.3); 2.4926 (49.9); 2.3330 (0.6); 2.3285 (0.8); 2.3241 (0.6); 1.1986 (10.0); 1.1815 (9.7); 1.1247 (13.5); 1.1077 (13.2); 0.0080 (1.5); −0.0002 (46.7); −0.0085 (1.8) I-081 [00205]
I-081: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 9.9065 (1.9); 7.8536 (1.9); 7.8318 (2.7); 7.7262 (2.8); 7.7182 (4.0); 7.7126 (1.7); 7.7037 (2.4); 7.7018 (2.4); 7.6956 (4.8); 7.6876 (0.6); 7.5551 (2.6); 7.5327 (2.5); 7.5118 (1.6); 7.5089 (1.6); 7.4816 (0.7); 7.4641 (1.1); 7.4462 (0.5); 7.3597 (0.5); 7.3562 (0.6); 7.3398 (1.1); 7.3221 (0.7); 7.3188 (0.6); 7.2673 (1.5); 7.2650 (1.5); 7.2479 (1.0); 6.7217 (0.6); 6.7080 (1.3); 6.6943 (0.6); 5.7560 (1.6); 4.2402 (1.0); 4.1952 (1.8); 4.1070 (2.0); 4.0619 (1.1); 3.4321 (1.9); 3.4167 (4.2); 3.4012 (2.7); 3.3840 (1.7); 3.3696 (1.7); 3.3525 (0.8); 3.3282 (26.0); 3.2338 (16.0); 2.7344 (0.7); 2.7173 (1.0); 2.7002 (0.7); 2.5242 (0.6); 2.5194 (1.0); 2.5107 (13.5); 2.5063 (27.3); 2.5017 (35.9); 2.4971 (26.3); 2.4926 (12.8); 1.8841 (0.5); 1.8680 (1.5); 1.8511 (2.1); 1.8345 (1.4); 1.8182 (0.4); 1.1989 (3.3); 1.1819 (3.2); 1.1249 (4.5); 1.1078 (4.4); 0.0080 (0.4); −0.0002 (13.6); −0.0085 (0.4) I-082 [00206]
I-082: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 11.8287 (4.1); 10.0303 (3.8); 8.1758 (5.1); 8.0076 (1.8); 7.9859 (10.0); 7.9761 (7.9); 7.9543 (1.7); 7.7553 (0.5); 7.7472 (5.2); 7.7419 (1.9); 7.7302 (2.1); 7.7247 (6.9); 7.7166 (0.8); 7.5780 (4.2); 7.5569 (3.4); 7.3719 (1.5); 7.3533 (3.1); 7.3218 (1.0); 7.3150 (1.1); 7.3067 (1.2); 7.3004 (1.7); 7.2951 (0.8); 7.2883 (0.8); 7.2808 (1.0); 7.2483 (0.5); 7.2449 (0.5); 7.2285 (2.4); 7.2252 (2.8); 7.2194 (3.5); 7.2131 (4.7); 7.2002 (0.6); 6.7969 (1.1); 6.7833 (2.2); 6.7695 (1.1); 4.5243 (1.6); 4.5104 (3.6); 4.4965 (1.6); 3.4261 (0.4); 3.4016 (1.1); 3.3855 (2.3); 3.3673 (2.3); 3.3517 (1.2); 3.3286 (35.1); 3.2516 (49.8); 3.1685 (0.4); 3.1516 (1.1); 3.1344 (1.6); 3.1172 (1.2); 3.0999 (0.5); 2.6714 (0.4); 2.5247 (1.2); 2.5112 (22.1); 2.5070 (43.2); 2.5025 (56.0); 2.4980 (41.3); 2.4939 (20.8); 2.3294 (0.3); 1.9362 (1.3); 1.9203 (2.5); 1.9025 (2.5); 1.8862 (1.2); 1.2013 (16.0); 1.1841 (15.8); 1.1544 (0.6); 0.0078 (0.5); −0.0002 (14.0); −0.0085 (0.5) I-083 [00207]
I-083: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 9.9405 (2.3); 7.8729 (2.2); 7.8512 (3.1); 7.7337 (6.0); 7.7112 (6.2); 7.7033 (0.8); 7.5421 (3.5); 7.5198 (2.9); 7.4140 (2.0); 7.3921 (2.2); 7.0592 (1.0); 7.0526 (1.1); 7.0376 (1.0); 7.0308 (1.0); 6.8921 (2.3); 6.8854 (2.2); 6.7094 (0.4); 6.6987 (1.2); 6.6869 (1.2); 6.6758 (0.4); 4.2294 (1.3); 4.1844 (1.9); 4.0729 (2.2); 4.0280 (1.4); 3.7581 (16.0); 3.3306 (42.2); 2.9129 (6.8); 2.9013 (6.8); 2.6712 (0.5); 2.6549 (0.8); 2.6380 (1.1); 2.6209 (0.8); 2.5244 (0.9); 2.5109 (14.7); 2.5066 (29.7); 2.5021 (39.5); 2.4975 (29.7); 2.4932 (15.2); 1.1599 (3.8); 1.1428 (3.8); 1.0954 (5.2); 1.0783 (5.1); 0.0079 (0.4); −0.0002 (11.4); −0.0084 (0.5) I-084 [00208]
I-084: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 11.8367 (2.5); 9.9950 (2.3); 8.1765 (3.0); 8.0201 (2.0); 7.9988 (5.0); 7.9685 (4.1); 7.9472 (1.8); 7.7551 (0.4); 7.7468 (3.5); 7.7415 (1.2); 7.7299 (1.3); 7.7243 (4.6); 7.7162 (0.5); 7.5651 (2.6); 7.5444 (2.1); 7.2620 (2.0); 7.2404 (2.3); 6.9059 (1.1); 6.8991 (1.3); 6.8844 (1.0); 6.8775 (1.3); 6.8292 (2.5); 6.8224 (2.1); 6.7671 (0.4); 6.7562 (1.2); 6.7445 (1.2); 6.7330 (0.4); 5.7558 (3.9); 3.7820 (0.4); 3.7452 (16.0); 3.7072 (0.5); 3.3294 (40.6); 3.0706 (0.7); 3.0535 (0.9); 3.0363 (0.7); 2.9299 (6.0); 2.9183 (6.0); 2.5247 (0.9); 2.5199 (1.4); 2.5113 (16.9); 2.5069 (34.1); 2.5023 (44.8); 2.4977 (32.8); 2.4933 (16.1); 1.1736 (9.8); 1.1564 (9.7); 1.1296 (0.4); 0.0080 (0.4); −0.0002 (12.9); −0.0085 (0.4) I-085 [00209]
I-085: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 8.3460 (4.4); 8.0352 (3.2); 8.0144 (4.1); 7.8182 (3.8); 7.7973 (3.3); 7.7204 (3.4); 7.6981 (4.7); 7.5842 (3.3); 7.5629 (2.6); 7.5201 (0.9); 7.5040 (2.0); 7.5007 (2.1); 7.4872 (1.2); 7.4695 (1.6); 7.4500 (0.6); 7.3567 (0.7); 7.3527 (0.7); 7.3368 (1.4); 7.3335 (1.4); 7.3196 (1.0); 7.3156 (1.0); 7.2737 (2.1); 7.2562 (1.3); 6.8958 (0.8); 6.8813 (1.5); 6.8672 (0.8); 4.7994 (1.1); 4.7856 (2.3); 4.7719 (1.1); 4.2793 (1.5); 4.2359 (2.6); 4.1618 (2.7); 4.1185 (1.4); 3.7111 (0.5); 3.6933 (1.8); 3.6871 (1.0); 3.6756 (2.0); 3.6694 (2.4); 3.6578 (0.9); 3.6517 (2.3); 3.6341 (0.7); 3.5525 (0.7); 3.5350 (2.2); 3.5289 (0.9); 3.5174 (2.4); 3.5111 (2.0); 3.4997 (1.0); 3.4934 (1.8); 3.4758 (0.6); 3.4226 (1.6); 3.4088 (2.8); 3.3950 (1.6); 3.3260 (22.3); 2.8069 (0.8); 2.7898 (1.1); 2.7727 (0.8); 2.7556 (0.3); 2.6712 (0.4); 2.5065 (45.8); 2.5022 (59.0); 2.4979 (45.8); 2.3291 (0.4); 1.1692 (5.5); 1.1520 (6.2); 1.1436 (6.3); 1.1302 (10.2); 1.1129 (16.0); 1.0954 (7.7); −0.0002 (12.1) I-086 [00210]
I-086: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 9.9051 (6.2); 8.3156 (0.6); 7.8454 (6.0); 7.8236 (8.6); 7.7387 (1.5); 7.7305 (12.0); 7.7221 (9.3); 7.7139 (6.2); 7.7081 (16.0); 7.6999 (7.6); 7.5542 (8.2); 7.5322 (8.5); 7.5118 (4.9); 7.5091 (4.9); 7.4815 (2.2); 7.4638 (3.4); 7.4439 (1.5); 7.3590 (1.7); 7.3557 (1.8); 7.3393 (3.5); 7.3216 (2.1); 7.3182 (2.0); 7.2659 (4.6); 7.2636 (4.7); 7.2465 (3.1); 7.2440 (3.0); 6.9702 (2.1); 6.9561 (4.3); 6.9417 (2.1); 6.0168 (1.0); 6.0034 (2.1); 5.9905 (1.8); 5.9777 (2.4); 5.9740 (1.4); 5.9641 (1.3); 5.9605 (2.6); 5.9474 (2.0); 5.9347 (2.5); 5.9213 (1.2); 5.7559 (2.5); 5.2539 (3.5); 5.2496 (3.7); 5.2109 (3.2); 5.2066 (3.3); 5.1084 (3.4); 5.1045 (3.4); 5.0827 (3.2); 5.0789 (3.2); 4.3513 (0.3); 4.2395 (3.3); 4.1945 (5.6); 4.1060 (6.5); 4.0610 (3.6); 3.9722 (3.6); 3.9585 (6.5); 3.9448 (3.5); 3.4719 (0.3); 3.4409 (0.4); 3.3290 (461.2); 2.7492 (0.8); 2.7323 (2.2); 2.7153 (3.1); 2.6981 (2.3); 2.6802 (1.5); 2.6755 (1.6); 2.6707 (2.0); 2.6662 (1.6); 2.6617 (0.8); 2.5242 (6.4); 2.5194 (10.1); 2.5107 (115.4); 2.5063 (233.0); 2.5018 (308.1); 2.4972 (226.5); 2.4928 (112.0); 2.3374 (0.7); 2.3332 (1.4); 2.3286 (2.0); 2.3241 (1.4); 2.3197 (0.7); 1.1974 (10.6); 1.1804 (10.4); 1.1238 (14.4); 1.1067 (14.2); 1.0451 (1.2); 1.0298 (1.2); 0.1460 (0.3); 0.0080 (2.9); −0.0002 (83.3); −0.0085 (2.9); −0.1497 (0.4) I-087 [00211]
I-087: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 8.3399 (12.1); 8.0318 (8.8); 8.0109 (11.2); 7.8132 (10.4); 7.7922 (8.8); 7.7558 (9.7); 7.7507 (3.8); 7.7387 (4.4); 7.7334 (12.6); 7.7257 (1.5); 7.5750 (8.1); 7.5539 (6.6); 7.5236 (1.9); 7.5198 (2.3); 7.5038 (5.5); 7.5002 (5.4); 7.4893 (3.1); 7.4867 (3.0); 7.4692 (4.0); 7.4522 (1.6); 7.4493 (1.6); 7.3563 (1.9); 7.3521 (1.9); 7.3365 (3.8); 7.3329 (3.5); 7.3192 (2.6); 7.3151 (2.5); 7.2745 (5.5); 7.2721 (5.4); 7.2551 (3.4); 7.2524 (3.1); 6.7379 (4.0); 6.7191 (4.2); 4.2781 (4.2); 4.2347 (7.2); 4.1612 (7.6); 4.1179 (4.1); 3.9337 (0.4); 3.9232 (0.8); 3.8971 (4.8); 3.8777 (5.1); 3.8691 (5.0); 3.8404 (0.4); 3.4380 (3.2); 3.4125 (5.6); 3.4086 (5.6); 3.3835 (3.0); 3.3268 (37.0); ; 2.8222 (0.8); 2.8054 (2.1); 2.7884 (3.0); 2.7713 (2.2); 2.7542 (0.9); 2.6755 (0.5); 2.6710 (0.7); 2.6666 (0.5); 2.5240 (2.7); 2.5064 (84.6); 2.5020 (108.3); 2.4976 (80.8); 2.3331 (0.5); 2.3289 (0.7); 2.3245 (0.5); 1.9594 (3.1); 1.9333 (3.7); 1.9283 (3.7); 1.6499 (1.1); 1.6386 (1.3); 1.6187 (2.7); 1.6095 (3.0); 1.5896 (2.8); 1.5806 (2.6); 1.5606 (1.1); 1.5498 (0.9); 1.2316 (0.4); 1.1689 (14.7); 1.1517 (16.0); 1.1431 (15.6); 1.1259 (14.2); 1.0956 (0.4); 1.0781 (0.3); 1.0746 (0.4); 1.0568 (0.4); 0.0077 (1.2); −0.0002 (27.2); −0.0083 (1.3) I-088 [00212]
I-088: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 8.3419 (11.5); 8.3136 (0.3); 8.0370 (8.6); 8.0162 (10.6); 7.8167 (10.1); 7.7959 (8.5); 7.7445 (9.4); 7.7221 (11.7); 7.5798 (8.4); 7.5588 (6.6); 7.5211 (2.4); 7.5048 (5.6); 7.5016 (5.5); 7.4908 (3.2); 7.4708 (4.0); 7.4532 (1.5); 7.4512 (1.5); 7.3578 (1.9); 7.3536 (1.9); 7.3378 (3.9); 7.3203 (2.5); 7.3166 (2.4); 7.2754 (5.5); 7.2563 (3.3); 6.8002 (2.1); 6.7867 (4.2); 6.7735 (2.1); 4.5212 (2.9); 4.5073 (6.2); 4.4935 (2.9); 4.2777 (4.0); 4.2344 (6.9); 4.1816 (0.4); 4.1623 (7.2); 4.1190 (3.8); 3.4738 (0.4); 3.4571 (0.7); 3.4399 (0.9); 3.4260 (1.6); 3.3983 (3.9); 3.3798 (8.3); 3.3502 (558.6); 3.2659 (3.5); 3.2512 (81.8); 3.2151 (0.4); 3.0714 (0.4); 2.8227 (0.9); 2.8056 (2.1); 2.7885 (2.9); 2.7716 (2.2); 2.7548 (0.9); 2.6727 (0.9); 2.5079 (119.7); 2.5037 (150.3); 2.4995 (116.0); 2.3305 (0.9); 1.9323 (2.5); 1.9156 (5.0); 1.8993 (5.1); 1.8825 (2.4); 1.2328 (0.5); 1.1693 (14.5); 1.1520 (16.0); 1.1434 (15.8); 1.1262 (14.0); 1.1007 (0.8); 1.0837 (0.6); 1.0748 (0.5); 1.0573 (0.8); 1.0402 (0.4); −0.0002 (31.1) I-089 [00213]
I-089: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 8.3433 (12.4); 8.3162 (3.9); 8.0321 (8.9); 8.0112 (11.3); 7.8154 (10.5); 7.7944 (8.9); 7.7706 (1.3); 7.7625 (10.1); 7.7572 (3.9); 7.7454 (4.5); 7.7401 (13.0); 7.7323 (1.8); 7.7220 (0.4); 7.5739 (8.1); 7.5530 (6.7); 7.5241 (1.9); 7.5203 (2.3); 7.5044 (5.5); 7.5007 (5.4); 7.4898 (3.1); 7.4869 (3.1); 7.4720 (3.7); 7.4695 (4.0); 7.4527 (1.6); 7.4495 (1.6); 7.3570 (1.9); 7.3527 (1.9); 7.3372 (3.9); 7.3333 (3.6); 7.3199 (2.6); 7.3157 (2.6); 7.2764 (5.5); 7.2738 (5.5); 7.2569 (3.4); 7.2540 (3.1); 6.7692 (2.1); 6.7554 (4.3); 6.7415 (2.1); 4.7631 (2.5); 4.7490 (5.4); 4.7348 (2.5); 4.2781 (4.3); 4.2347 (7.4); 4.1615 (7.8); 4.1182 (4.2); 3.6296 (2.1); 3.6145 (6.3); 3.5999 (7.2); 3.5852 (3.0); 3.4444 (2.6); 3.4301 (6.3); 3.4155 (5.8); 3.4006 (2.0); 3.3310 (107.3); 3.3074 (1.9); 2.8222 (0.8); 2.8055 (2.2); 2.7884 (3.0); 2.7712 (2.2); 2.7542 (0.9); 2.6755 (0.5); 2.6711 (0.7); 2.6670 (0.5); 2.5244 (2.7); 2.5108 (46.5); 2.5067 (89.2); 2.5022 (114.8); 2.4977 (85.1); 2.4935 (43.1); 2.3334 (0.5); 2.3290 (0.7); 2.3245 (0.5); 1.2309 (0.6); 1.1690 (14.8); 1.1519 (16.0); 1.1430 (15.7); 1.1259 (14.3); 1.1014 (0.6); 1.0840 (0.4); 0.0079 (1.1); −0.0002 (26.2); −0.0084 (1.1) I-090 [00214]
I-090: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 8.3653 (4.3); 8.0511 (3.2); 8.0302 (4.0); 7.8193 (3.7); 7.7983 (3.2); 7.7533 (0.4); 7.7452 (3.6); 7.7398 (1.4); 7.7283 (1.5); 7.7227 (4.7); 7.7146 (0.6); 7.5669 (2.8); 7.5461 (2.3); 7.4089 (2.1); 7.3870 (2.4); 7.0698 (1.3); 7.0630 (1.4); 7.0480 (1.2); 7.0411 (1.3); 6.8890 (2.9); 6.8821 (2.7); 6.7759 (0.4); 6.7653 (1.2); 6.7536 (1.2); 6.7418 (0.4); 4.2632 (1.6); 4.2199 (2.4); 4.1265 (2.6); 4.0832 (1.6); 3.8160 (0.4); 3.7701 (0.4); 3.7568 (16.0); 3.6795 (0.4); 3.3291 (57.2); 2.9278 (6.4); 2.9162 (6.5); 2.7227 (0.7); 2.7054 (1.0); 2.6884 (0.8); 2.6710 (0.6); 2.5244 (1.0); 2.5109 (22.3); 2.5067 (44.1); 2.5022 (57.6); 2.4976 (42.5); 2.4932 (21.2); 2.3290 (0.3); 1.1365 (5.0); 1.1194 (5.1); 1.1076 (5.2); 1.0905 (4.9); 1.0739 (0.4); 1.0564 (0.3); 0.0078 (2.2); −0.0002 (51.0); −0.0085 (2.0) I-091 [00215]
I-091: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 8.1435 (4.6); 8.1267 (3.8); 7.9952 (2.8); 7.9743 (3.5); 7.7499 (0.4); 7.7416 (3.2); 7.7361 (1.1); 7.7246 (1.3); 7.7190 (4.3); 7.7065 (3.3); 7.6856 (2.8); 7.5628 (2.4); 7.5422 (1.9); 7.4405 (1.0); 7.4219 (1.5); 7.3709 (0.6); 7.3635 (0.7); 7.3567 (0.7); 7.3495 (1.0); 7.3448 (0.5); 7.3364 (0.6); 7.3298 (0.7); 7.2955 (0.5); 7.2831 (3.5); 7.2767 (1.8); 7.2691 (1.1); 7.2655 (1.0); 6.7563 (0.4); 6.7456 (1.0); 6.7338 (1.0); 4.0769 (0.7); 4.0530 (0.9); 4.0327 (0.4); 3.9182 (0.4); 3.9039 (0.8); 3.8895 (0.6); 3.8795 (0.6); 3.3418 (18.6); 3.0591 (0.3); 3.0424 (0.7); 3.0252 (0.9); 3.0080 (0.7); 2.9237 (5.6); 2.9122 (5.6); 2.6763 (0.5); 2.6718 (0.6); 2.6672 (0.4); 2.5253 (2.2); 2.5118 (39.0); 2.5074 (75.7); 2.5028 (96.8); 2.4982 (69.6); 2.4938 (33.5); 2.3342 (0.4); 2.3296 (0.6); 2.3251 (0.4); 2.0748 (16.0); 1.1991 (4.0); 1.1881 (4.7); 1.1823 (4.6); 1.1712 (3.9); 0.0080 (2.0); −0.0002 (51.4); −0.0085 (1.8) I-092 [00216]
I-092: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 8.3526 (10.3); 8.3191 (4.1); 8.0562 (8.2); 8.0357 (9.9); 7.8259 (9.5); 7.8053 (8.3); 7.7499 (8.0); 7.7278 (10.5); 7.6072 (8.6); 7.5860 (6.6); 7.5217 (2.5); 7.5038 (6.0); 7.4896 (3.6); 7.4712 (4.3); 7.4525 (1.8); 7.3550 (1.9); 7.3377 (4.1); 7.3202 (2.6); 7.2775 (6.4); 7.2570 (6.6); 4.2813 (3.0); 4.2381 (6.0); 4.1637 (5.9); 4.1204 (3.0); 3.6020 (5.0); 3.5899 (5.4); 3.3388 (21.2); 2.9280 (5.4); 2.9118 (10.1); 2.8955 (4.9); 2.8255 (0.9); 2.8084 (2.2); 2.7916 (2.9); 2.7745 (2.2); 2.7573 (1.0); 2.6721 (0.4); 2.5031 (59.4); 2.3299 (0.4); 1.1708 (13.9); 1.1535 (16.0); 1.1448 (15.7); 1.1275 (13.4); 1.0753 (0.5); 1.0581 (0.6); 1.0407 (0.3); −0.0002 (18.2) I-093 [00217]
I-093: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 11.8390 (3.3); 10.0361 (3.0); 8.1759 (4.0); 8.0261 (1.9); 8.0046 (7.1); 7.9881 (5.6); 7.9667 (1.7); 7.7658 (0.4); 7.7579 (4.3); 7.7526 (1.6); 7.7410 (1.7); 7.7355 (5.7); 7.7275 (0.7); 7.5870 (3.4); 7.5660 (2.8); 7.3722 (1.2); 7.3538 (2.4); 7.3222 (0.8); 7.3162 (0.9); 7.3066 (1.0); 7.3010 (1.4); 7.2880 (0.6); 7.2813 (0.8); 7.2480 (0.5); 7.2446 (0.4); 7.2285 (1.8); 7.2251 (2.0); 7.2170 (2.8); 7.2107 (3.8); 7.1981 (0.6); 7.0880 (0.9); 7.0745 (1.8); 7.0605 (0.9); 3.8001 (0.8); 3.7841 (2.0); 3.7685 (2.0); 3.7527 (1.0); 3.5203 (1.9); 3.5036 (3.4); 3.4868 (1.5); 3.3309 (68.0); 3.1657 (0.4); 3.1485 (0.9); 3.1312 (1.3); 3.1141 (1.0); 3.0970 (0.5); 3.0756 (16.0); 2.6757 (0.6); 2.6711 (0.7); 2.6667 (0.5); 2.5245 (2.6); 2.5109 (46.0); 2.5067 (91.0); 2.5022 (118.8); 2.4977 (88.3); 2.4933 (44.8); 2.3335 (0.6); 2.3291 (0.8); 2.3245 (0.6); 1.1997 (12.9); 1.1825 (12.8); 0.1460 (0.4); 0.0078 (3.5); −0.0002 (85.2); −0.0085 (3.6); −0.1497 (0.4) I-094 [00218]
I-094: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 11.8404 (4.0); 10.0363 (3.8); 8.1774 (4.9); 8.0208 (2.4); 7.9994 (8.7); 7.9839 (7.4); 7.9627 (2.6); 7.7501 (4.8); 7.7449 (2.1); 7.7277 (6.6); 7.7198 (1.4); 7.6063 (4.4); 7.5850 (3.6); 7.3730 (1.6); 7.3541 (3.1); 7.3222 (1.2); 7.3154 (1.3); 7.3074 (1.5); 7.3010 (1.8); 7.2889 (1.1); 7.2814 (1.1); 7.2709 (0.5); 7.2491 (1.5); 7.2386 (2.8); 7.2256 (4.4); 7.2205 (4.6); 7.2140 (5.4); 7.2015 (1.4); 3.6192 (1.2); 3.6039 (3.1); 3.5892 (3.3); 3.5736 (1.6); 3.3323 (44.4); 3.2756 (0.6); 3.1666 (0.5); 3.1499 (1.2); 3.1326 (1.6); 3.1156 (1.3); 3.0982 (0.6); 2.9262 (3.0); 2.9100 (6.0); 2.8937 (3.1); 2.6714 (0.5); 2.5067 (69.8); 2.5024 (85.8); 2.4981 (65.7); 2.3295 (0.6); 2.3253 (0.4); 1.2007 (15.5); 1.1836 (16.0); −0.0002 (53.4); −0.0085 (4.9); −0.0576 (0.7) I-095 [00219]
I-095: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 8.3531 (5.4); 8.3176 (1.0); 8.0614 (4.0); 8.0406 (5.0); 7.8274 (4.6); 7.8065 (4.0); 7.7569 (4.3); 7.7397 (1.9); 7.7345 (5.6); 7.5892 (3.7); 7.5679 (3.0); 7.5215 (1.1); 7.5052 (2.5); 7.5019 (2.5); 7.4904 (1.4); 7.4877 (1.4); 7.4704 (1.8); 7.4533 (0.7); 7.4505 (0.7); 7.3576 (0.8); 7.3535 (0.8); 7.3378 (1.8); 7.3204 (1.1); 7.3165 (1.1); 7.2767 (2.5); 7.2748 (2.5); 7.2576 (1.6); 7.0987 (0.9); 7.0853 (1.8); 7.0715 (0.9); 4.2813 (1.8); 4.2380 (3.2); 4.1630 (3.4); 4.1197 (1.8); 3.7966 (0.8); 3.7810 (2.1); 3.7657 (2.2); 3.7497 (1.0); 3.5214 (2.1); 3.5047 (3.6); 3.4877 (1.7); 3.3330 (45.7); 3.3095 (0.7); 3.0784 (16.0); 2.8231 (0.4); 2.8062 (1.0); 2.7892 (1.4); 2.7721 (1.0); 2.7551 (0.4); 2.6713 (0.4); 2.5067 (50.0); 2.5023 (63.3); 2.4979 (47.6); 2.3293 (0.4); 1.1695 (6.6); 1.1524 (7.1); 1.1435 (7.0); 1.1263 (6.4); −0.0002 (29.6) I-096 [00220]
I-096: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 11.8550 (2.1); 10.8487 (0.8); 10.0754 (2.4); 8.1912 (3.6); 8.1723 (0.4); 8.0417 (16.0); 7.9695 (1.4); 7.7809 (3.5); 7.7755 (1.3); 7.7637 (1.5); 7.7584 (4.5); 7.7503 (0.5); 7.5787 (3.1); 7.5563 (2.7); 7.3744 (1.0); 7.3555 (1.8); 7.3254 (0.7); 7.3211 (0.8); 7.3043 (1.2); 7.2892 (0.6); 7.2845 (0.7); 7.2482 (0.5); 7.2445 (0.5); 7.2286 (1.4); 7.2250 (1.5); 7.2115 (1.3); 7.2067 (2.5); 7.2017 (2.1); 7.1865 (0.7); 3.3322 (98.5); 3.1537 (0.7); 3.1365 (1.0); 3.1191 (0.8); 2.6760 (0.6); 2.6714 (0.8); 2.6669 (0.6); 2.5249 (2.5); 2.5200 (3.8); 2.5114 (44.5); 2.5070 (89.3); 2.5025 (116.9); 2.4979 (85.4); 2.4934 (41.8); 2.3338 (0.5); 2.3293 (0.7); 2.3247 (0.5); 2.0405 (8.6); 1.2009 (11.0); 1.1837 (10.9); 0.0080 (2.3); −0.0001 (66.6); −0.0084 (2.4) I-097 [00221]
I-097: .sup.1H-NMR(400.2 MHz, CDCl3): δ = 8.1479 (8.2); 8.0831 (6.5); 8.0622 (7.4); 7.8660 (0.6); 7.8438 (4.6); 7.8367 (4.3); 7.8144 (0.6); 7.7341 (7.2); 7.7133 (6.3); 7.6359 (0.8); 7.6279 (7.1); 7.6225 (2.6); 7.6115 (4.1); 7.6055 (9.0); 7.5971 (1.4); 7.5904 (2.8); 7.5825 (0.4); 7.5196 (2.2); 7.5099 (2.4); 7.4834 (0.9); 7.4764 (4.2); 7.4725 (6.8); 7.4710 (6.8); 7.4644 (4.4); 7.4583 (3.3); 7.4557 (2.9); 7.4384 (0.6); 7.4357 (0.6); 7.3791 (5.7); 7.3777 (5.7); 7.3572 (5.0); 7.3392 (1.9); 7.3311 (1.5); 7.3245 (1.3); 7.3193 (2.1); 7.3122 (1.6); 7.3044 (1.4); 7.2973 (1.4); 7.2609 (30.8); 7.2111 (1.2); 7.1917 (1.1); 7.1813 (4.0); 7.1626 (2.7); 5.9192 (1.6); 5.9162 (1.6); 5.8659 (5.1); 5.8628 (4.9); 4.3109 (0.7); 4.2981 (1.9); 4.2854 (2.2); 4.2719 (1.1); 3.1417 (15.1); 3.1291 (14.9); 2.8830 (0.7); 2.8773 (0.7); 2.8660 (1.7); 2.8602 (1.1); 2.8488 (2.3); 2.8317 (1.7); 2.8148 (0.6); 1.8740 (5.5); 1.8711 (5.4); 1.7974 (16.0); 1.7947 (15.5); 1.5816 (15.4); 1.2543 (11.8); 1.2373 (11.4); 1.1922 (12.5); 1.1749 (12.4); 1.1570 (4.0); 1.1399 (3.8); 0.0078 (2.4); −0.0002 (57.1); −0.0085 (2.1) I-098 [00222]
I-098: .sup.1H-NMR(400.2 MHz, CDCl3): δ = 8.2762 (8.3); 8.1401 (7.4); 8.1192 (8.4); 7.8941 (0.4); 7.8725 (0.4); 7.7792 (8.1); 7.7584 (7.2); 7.7170 (0.7); 7.6957 (0.4); 7.6323 (8.0); 7.6270 (2.7); 7.6153 (3.4); 7.6100 (9.8); 7.6020 (1.1); 7.5956 (0.6); 7.5212 (0.6); 7.5063 (0.4); 7.4815 (5.3); 7.4702 (7.8); 7.3903 (5.9); 7.3696 (5.2); 7.3545 (1.3); 7.3413 (1.7); 7.3325 (1.7); 7.3275 (1.3); 7.3239 (1.4); 7.3191 (1.0); 7.3130 (0.7); 7.2623 (96.8); 7.1889 (2.3); 7.1694 (2.1); 7.1608 (2.0); 7.1410 (1.7); 6.9985 (0.5); 5.3013 (7.9); 4.3347 (0.8); 4.3234 (2.0); 4.3107 (2.1); 4.2625 (0.6); 4.2451 (1.8); 4.2270 (2.0); 4.2118 (2.3); 4.1939 (2.2); 4.1753 (0.6); 3.1508 (16.0); 3.1383 (15.7); 2.8664 (0.4); 2.8478 (1.2); 2.8307 (2.0); 2.8128 (2.1); 2.7953 (1.3); 2.7791 (0.4); 1.7968 (7.4); 1.7909 (8.8); 1.7787 (7.3); 1.7728 (8.1); 1.5749 (97.6); 1.2934 (0.4); 1.2460 (8.6); 1.2405 (7.2); 1.2289 (8.7); 1.2233 (7.3); 1.2144 (8.5); 1.2108 (9.4); 1.1972 (8.2); 1.1936 (9.0); 1.1660 (0.4); 1.1565 (0.5); 1.1483 (0.4); 1.1407 (0.3); 0.1459 (0.7); 0.0079 (7.9); −0.0002 (176.2); −0.0084 (6.2); −0.1499 (0.7) I-099 [00223]
I-099: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 10.8646 (2.4); 8.3809 (7.5); 8.3500 (0.4); 8.0995 (5.4); 8.0788 (6.9); 7.9938 (0.4); 7.8733 (6.4); 7.8523 (5.6); 7.8389 (0.7); 7.8140 (0.4); 7.7971 (1.0); 7.7903 (1.2); 7.7776 (5.8); 7.7553 (7.5); 7.7387 (0.7); 7.5783 (6.2); 7.5561 (5.4); 7.5225 (1.6); 7.5031 (3.7); 7.4888 (2.1); 7.4714 (2.8); 7.4517 (1.1); 7.3550 (1.4); 7.3359 (2.7); 7.3218 (1.6); 7.3182 (1.7); 7.2796 (3.8); 7.2599 (2.2); 6.7520 (0.3); 4.2881 (2.6); 4.2446 (4.5); 4.1921 (0.4); 4.1686 (4.7); 4.1253 (2.5); 4.0380 (0.5); 4.0201 (0.5); 3.7935 (0.5); 3.7768 (0.5); 3.5685 (11.8); 3.3312 (87.9); 2.8255 (0.6); 2.8086 (1.5); 2.7917 (2.0); 2.7745 (1.4); 2.7567 (0.6); 2.6717 (0.6); 2.5068 (70.1); 2.5027 (92.8); 2.4985 (73.0); 2.3338 (0.4); 2.3295 (0.6); 2.0409 (16.0); 2.0115 (1.8); 2.0000 (0.4); 1.9891 (2.2); 1.2983 (0.5); 1.2582 (0.7); 1.2339 (0.7); 1.1929 (0.8); 1.1705 (9.6); 1.1533 (10.3); 1.1450 (10.6); 1.1278 (9.4); 1.0993 (0.8); 1.0818 (0.7); 1.0700 (0.5); 0.8883 (2.0); 0.8716 (1.9); 0.0078 (2.2); −0.0003 (49.6) I-100 [00224]
I-100: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 11.8365 (4.1); 10.0358 (3.8); 8.1772 (5.0); 8.0166 (2.2); 7.9952 (9.0); 7.9809 (7.2); 7.9594 (2.0); 7.7717 (0.6); 7.7638 (5.2); 7.7587 (2.1); 7.7467 (2.2); 7.7414 (6.7); 7.5843 (5.0); 7.5622 (4.3); 7.5497 (2.5); 7.5291 (2.4); 7.3727 (1.6); 7.3539 (3.1); 7.3223 (1.0); 7.3151 (1.2); 7.3077 (1.3); 7.3010 (1.7); 7.2951 (0.8); 7.2891 (0.8); 7.2813 (1.0); 7.2489 (0.5); 7.2290 (2.5); 7.2259 (3.1); 7.2215 (3.7); 7.2142 (4.9); 7.2024 (0.6); 5.1677 (0.8); 5.1461 (1.5); 5.1251 (1.6); 5.1037 (0.8); 3.6077 (2.2); 3.5849 (4.5); 3.5621 (2.5); 3.3313 (39.3); 3.3162 (4.7); 3.2940 (2.1); 3.1679 (0.4); 3.1505 (1.2); 3.1334 (1.6); 3.1162 (1.2); 3.0987 (0.5); 2.6717 (0.4); 2.5071 (49.0); 2.5027 (63.3); 2.4983 (46.7); 2.3296 (0.4); 2.0749 (0.3); 1.9892 (0.4); 1.2386 (0.4); 1.2213 (0.6); 1.2012 (16.0); 1.1840 (15.8); 0.0077 (0.7); −0.0002 (13.9) I-101 [00225]
I-101: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 8.3481 (11.1); 8.0488 (8.2); 8.0281 (10.3); 7.8210 (9.6); 7.8002 (8.4); 7.7616 (8.7); 7.7392 (11.1); 7.5857 (9.1); 7.5633 (8.8); 7.5380 (4.3); 7.5217 (2.6); 7.5047 (5.7); 7.5020 (5.7); 7.4903 (3.4); 7.4711 (4.2); 7.4513 (1.6); 7.3576 (1.8); 7.3537 (1.8); 7.3378 (3.9); 7.3205 (2.5); 7.3168 (2.5); 7.2747 (5.6); 7.2569 (3.4); 5.1862 (0.3); 5.1648 (1.4); 5.1434 (2.7); 5.1224 (2.8); 5.1010 (1.5); 5.0795 (0.4); 4.2794 (3.8); 4.2360 (6.7); 4.1627 (7.0); 4.1194 (3.7); 3.6194 (0.8); 3.6017 (4.0); 3.5791 (8.0); 3.5564 (4.4); 3.3400 (299.8); 3.3143 (9.4); 3.2923 (4.2); 2.8224 (0.8); 2.8057 (2.1); 2.7887 (2.9); 2.7719 (2.2); 2.7546 (0.9); 2.6717 (0.8); 2.5072 (107.9); 2.5031 (135.2); 2.4991 (104.4); 2.3298 (0.8); 1.1694 (14.2); 1.1522 (16.0); 1.1439 (15.7); 1.1266 (13.7); 1.0743 (0.4); 1.0569 (0.5); −0.0002 (19.6) I-102 [00226]
I-102: .sup.1H-NMR(600.1 MHz, CDCl3): δ = 8.5963 (0.9); 8.0828 (2.8); 8.0691 (3.0); 7.7288 (1.2); 7.7167 (1.2); 7.6292 (0.5); 7.6238 (4.7); 7.6203 (1.5); 7.6125 (1.6); 7.6089 (5.3); 7.6036 (0.6); 7.3586 (3.2); 7.3445 (2.8); 7.2893 (1.5); 7.2872 (1.6); 7.2765 (1.8); 7.2744 (1.8); 7.2596 (16.5); 7.1426 (0.6); 7.1406 (0.6); 7.1301 (1.4); 7.1283 (1.4); 7.1177 (1.0); 7.1156 (0.9); 7.0879 (1.0); 7.0862 (1.1); 7.0754 (1.5); 7.0738 (1.5); 7.0631 (0.6); 7.0614 (0.6); 6.8317 (1.3); 6.8192 (1.2); 4.6051 (0.7); 4.5984 (0.7); 3.8807 (1.7); 3.8706 (2.9); 3.8603 (1.7); 3.1529 (0.4); 3.1414 (1.0); 3.1299 (1.4); 3.1184 (1.1); 3.1084 (8.6); 3.1002 (8.3); 2.9224 (2.0); 2.9124 (2.7); 2.9022 (2.2); 2.4239 (0.6); 2.4137 (1.4); 2.4036 (2.1); 2.3934 (1.3); 2.3832 (0.5); 1.5877 (1.7); 1.4269 (0.3); 1.3331 (0.5); 1.2843 (0.7); 1.2555 (16.0); 1.2440 (15.3); 0.0053 (0.4); −0.00001 (11.2); −0.0056 (0.3) I-103 [00227]
I-103: .sup.1H-NMR(400.2 MHz, CDCl3): δ = 9.5144 (0.7); 8.1708 (0.6); 8.0919 (0.8); 8.0711 (0.9); 7.8443 (0.7); 7.8232 (0.6); 7.7395 (0.8); 7.7191 (0.8); 7.6318 (1.0); 7.6149 (1.0); 7.6096 (1.3); 7.5929 (0.6); 7.5328 (0.3); 7.5254 (0.5); 7.4945 (1.2); 7.4830 (0.9); 7.3845 (1.2); 7.3627 (1.0); 7.3464 (0.4); 7.3374 (0.3); 7.2908 (0.3); 7.2626 (34.0); 7.2474 (0.4); 6.2771 (0.4); 6.2311 (0.6); 4.1485 (0.6); 3.1639 (0.4); 3.1470 (2.2); 3.1416 (1.5); 3.1344 (2.0); 3.1291 (1.3); 2.8572 (0.3); 2.7198 (10.4); 1.6005 (16.0); 1.5590 (1.3); 1.5450 (1.7); 1.5284 (1.5); 1.4558 (1.4); 1.4391 (1.4); 1.2975 (0.3); 1.2935 (0.3); 1.2590 (1.7); 1.2422 (1.6); 1.2070 (1.6); 1.2012 (1.1); 1.1898 (1.6); 1.1839 (1.0); 1.1471 (0.8); 1.1301 (0.7); −0.0003 (56.7) I-104 [00228]
I-104: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 11.9530 (4.0); 10.1074 (3.6); 8.4825 (0.8); 8.4627 (1.5); 8.4430 (0.9); 8.3996 (5.1); 7.7994 (2.2); 7.7786 (2.2); 7.7514 (2.8); 7.7457 (6.3); 7.7404 (2.3); 7.7285 (2.6); 7.7231 (9.0); 7.5706 (4.4); 7.5496 (3.5); 7.3779 (1.5); 7.3591 (2.8); 7.3291 (1.1); 7.3248 (1.2); 7.3118 (1.7); 7.3082 (1.9); 7.2935 (0.9); 7.2886 (1.0); 7.2521 (0.9); 7.2485 (0.8); 7.2325 (2.2); 7.2291 (2.2); 7.2127 (4.8); 7.2085 (3.3); 7.1934 (1.1); 6.8198 (0.6); 6.8090 (1.8); 6.7976 (1.8); 6.7862 (0.6); 3.3326 (52.1); 3.1604 (0.4); 3.1433 (1.1); 3.1262 (1.6); 3.1089 (1.2); 3.0920 (0.5); 2.9268 (9.7); 2.9153 (9.6); 2.6717 (0.4); 2.5250 (1.2); 2.5112 (25.9); 2.5072 (50.9); 2.5027 (65.6); 2.4982 (48.0); 2.4940 (24.1); 2.3295 (0.4); 1.2385 (0.5); 1.2214 (0.6); 1.1995 (16.0); 1.1823 (16.0); 1.1677 (1.1); 1.1578 (0.8); 1.1502 (0.5); 1.1377 (1.4); 1.1206 (1.1); 0.0078 (1.1); −0.0002 (28.8); −0.0083 (1.1) I-105 [00229]
I-105: .sup.1H-NMR(400 MHz, d.sub.6-DMSO): δ = 8.5651 (0.3); 8.3593 (10.6); 8.3165 (0.5); 8.0020 (2.1); 7.9822 (4.0); 7.9631 (3.0); 7.9029 (4.4); 7.8804 (2.9); 7.7761 (0.3); 7.7464 (12.0); 7.7238 (12.2); 7.7058 (0.6); 7.5734 (7.6); 7.5526 (6.3); 7.5261 (2.0); 7.5100 (4.9); 7.5065 (4.9); 7.4967 (2.9); 7.4942 (2.9); 7.4766 (3.7); 7.4597 (1.5); 7.4569 (1.4); 7.3609 (1.7); 7.3566 (1.7); 7.3411 (3.6); 7.3373 (3.3); 7.3238 (2.4); 7.3197 (2.4); 7.2806 (5.0); 7.2783 (5.0); 7.2612 (3.1); 7.2586 (2.9); 7.1822 (0.4); 6.8357 (1.2); 6.8252 (3.0); 6.8137 (3.0); 6.8031 (1.1); 4.6244 (0.3); 4.2934 (3.9); 4.2500 (6.4); 4.1717 (6.7); 4.1283 (3.7); 3.3320 (379.7); 2.9245 (16.0); 2.9129 (15.7); 2.8148 (0.8); 2.7983 (1.9); 2.7810 (2.6); 2.7640 (2.0); 2.7474 (0.9); 2.6759 (1.7); 2.6716 (2.2); 2.6671 (1.7); 2.5248 (6.7); 2.5070 (277.2); 2.5026 (356.6); 2.4982 (266.3); 2.3339 (1.6); 2.3294 (2.2); 2.3248 (1.6); 2.3004 (0.9); 2.0953 (0.6); 1.2389 (1.2); 1.2218 (1.1); 1.1972 (0.7); 1.1869 (0.9); 1.1789 (1.3); 1.1655 (13.3); 1.1482 (15.0); 1.1419 (15.2); 1.1246 (13.3); 1.0812 (0.8); 1.0722 (0.5); 1.0633 (0.7); 0.1460 (0.5); 0.0080 (4.4); −0.0001 (128.7); −0.0083 (6.4); −0.1494 (0.5) I-106 [00230]
I-106: .sup.1H-NMR(400.2 MHz, CDCl3): δ = 8.2596 (7.2); 7.8445 (4.5); 7.8238 (7.3); 7.7510 (7.0); 7.7292 (10.1); 7.7119 (2.2); 7.7065 (7.4); 7.4865 (5.5); 7.4767 (6.6); 7.3701 (4.6); 7.3619 (2.2); 7.3497 (5.3); 7.3420 (2.7); 7.3307 (2.2); 7.3197 (1.1); 7.2624 (49.5); 7.1786 (3.3); 7.1592 (2.8); 6.0197 (8.4); 5.3010 (6.3); 4.0443 (0.4); 4.0007 (8.5); 3.9973 (9.3); 3.9538 (0.4); 3.8632 (6.7); 2.8615 (0.5); 2.8439 (1.4); 2.8266 (1.9); 2.8095 (1.4); 2.7925 (0.6); 2.0090 (6.6); 1.5869 (53.7); 1.2929 (0.3); 1.2616 (0.4); 1.2387 (10.5); 1.2222 (16.0); 1.2068 (10.3); 0.1460 (0.4); 0.0079 (2.8); −0.0002 (85.5); −0.1498 (0.4) I-107 [00231]
I-107: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 12.1272 (2.9); 9.4770 (3.0); 8.3485 (3.9); 8.3373 (0.4); 7.7564 (0.6); 7.7483 (4.6); 7.7428 (1.7); 7.7314 (1.9); 7.7257 (6.1); 7.7176 (0.7); 7.6549 (3.8); 7.6308 (3.8); 7.5763 (3.5); 7.5557 (2.9); 7.4511 (1.6); 7.4483 (1.6); 7.4319 (1.9); 7.4290 (1.8); 7.3647 (1.3); 7.3610 (1.4); 7.3454 (2.2); 7.3418 (2.2); 7.2962 (1.0); 7.2929 (1.0); 7.2777 (1.9); 7.2747 (1.8); 7.2589 (1.1); 7.2554 (1.0); 7.2371 (1.4); 7.2330 (1.4); 7.2180 (1.8); 7.2142 (1.7); 7.1995 (0.8); 7.1956 (0.7); 6.8845 (0.5); 6.8735 (1.5); 6.8619 (1.5); 6.8505 (0.5); 3.3290 (38.3); 3.1088 (0.4); 3.0912 (1.0); 3.0741 (1.4); 3.0568 (1.0); 3.0398 (0.4); 2.9236 (8.3); 2.9120 (8.2); 2.6764 (0.4); 2.6718 (0.6); 2.6672 (0.4); 2.5253 (1.7); 2.5205 (2.7); 2.5117 (33.3); 2.5074 (66.2); 2.5029 (85.1); 2.4983 (61.3); 2.4939 (29.6); 2.3343 (0.4); 2.3297 (0.5); 2.3252 (0.4); 1.2389 (0.5); 1.2217 (0.6); 1.2021 (16.0); 1.1849 (15.8); 1.1586 (0.4); 1.1376 (0.5); 1.1205 (0.3); 0.0079 (1.4); −0.0002 (39.6); −0.0086 (1.4) I-108 [00232]
I-108: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 11.9206 (4.0); 10.1542 (3.6); 8.2846 (3.3); 8.1424 (5.0); 7.9981 (3.4); 7.9778 (4.4); 7.8068 (2.1); 7.8035 (2.1); 7.7863 (1.8); 7.7830 (1.8); 7.7694 (0.4); 7.7503 (5.6); 7.7451 (2.5); 7.7333 (2.6); 7.7278 (7.1); 7.5708 (4.7); 7.5499 (3.7); 7.3953 (0.4); 7.3817 (2.3); 7.3609 (3.0); 7.3411 (0.5); 7.3315 (1.4); 7.3278 (1.4); 7.3108 (2.0); 7.2950 (1.2); 7.2911 (1.2); 7.2792 (0.3); 7.2538 (1.1); 7.2501 (1.3); 7.2342 (2.3); 7.2309 (2.5); 7.2170 (1.9); 7.2136 (2.0); 7.2062 (3.2); 7.2027 (3.2); 7.1866 (1.5); 7.1832 (1.5); 7.1635 (0.4); 6.8017 (0.7); 6.7908 (1.8); 6.7793 (1.8); 6.7683 (0.7); 3.3364 (18.4); 3.1669 (0.5); 3.1495 (1.2); 3.1323 (1.6); 3.1152 (1.2); 3.0988 (0.5); 2.9297 (0.8); 2.9112 (9.8); 2.8996 (9.8); 2.7508 (0.4); 2.7394 (0.4); 2.6718 (0.4); 2.5073 (43.5); 2.5029 (55.1); 2.4984 (40.4); 2.3294 (0.3); 2.3001 (1.2); 1.2384 (1.0); 1.2211 (1.4); 1.2056 (16.0); 1.1885 (16.0); 1.1740 (2.3); 1.1562 (1.4); 1.1267 (0.3); 0.0078 (1.0); −0.0002 (20.1); −0.0085 (0.9) I-109 [00233]
I-109: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 11.9152 (4.1); 10.1650 (3.6); 8.1615 (1.8); 8.1487 (4.3); 8.1314 (1.8); 8.0785 (1.6); 8.0588 (3.1); 8.0392 (1.8); 7.7437 (0.7); 7.7356 (5.5); 7.7302 (2.2); 7.7185 (2.4); 7.7131 (7.3); 7.7051 (0.9); 7.6220 (2.2); 7.6187 (2.2); 7.6016 (2.0); 7.5984 (2.0); 7.5685 (4.5); 7.5476 (3.6); 7.3831 (1.4); 7.3799 (1.5); 7.3635 (2.7); 7.3606 (2.8); 7.3318 (1.3); 7.3286 (1.3); 7.3110 (2.2); 7.2949 (1.1); 7.2916 (1.1); 7.2524 (1.1); 7.2487 (1.1); 7.2329 (2.2); 7.2295 (2.2); 7.2154 (1.5); 7.2117 (1.5); 7.1910 (3.0); 7.1883 (3.0); 7.1718 (1.6); 6.7887 (0.7); 6.7782 (1.9); 6.7665 (1.8); 6.7558 (0.6); 3.3328 (32.2); 3.1654 (0.4); 3.1484 (1.1); 3.1311 (1.6); 3.1139 (1.2); 3.0967 (0.5); 2.9190 (10.2); 2.9074 (10.1); 2.5250 (1.0); 2.5115 (21.6); 2.5073 (42.1); 2.5029 (54.1); 2.4984 (39.7); 2.4941 (20.0); 2.3296 (0.3); 1.2389 (0.6); 1.2217 (0.8); 1.2016 (16.0); 1.1844 (15.9); 1.1680 (1.3); 1.1585 (1.0); 1.1507 (0.9); 1.1383 (1.5); 1.1212 (1.2); 0.0079 (1.0); −0.0002 (24.8); −0.0084 (1.1) I-110 [00234]
I-110: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 8.3650 (9.1); 8.1106 (2.3); 8.0909 (4.4); 8.0714 (2.6); 7.7361 (8.0); 7.7138 (10.4); 7.6760 (3.8); 7.6555 (3.5); 7.6135 (3.4); 7.5817 (4.3); 7.5712 (7.4); 7.5499 (5.8); 7.5213 (2.1); 7.5049 (4.7); 7.5019 (4.7); 7.4902 (2.7); 7.4707 (3.6); 7.4508 (1.4); 7.3573 (1.6); 7.3534 (1.5); 7.3373 (3.4); 7.3201 (2.2); 7.3165 (2.2); 7.2786 (4.8); 7.2595 (2.9); 6.8024 (1.2); 6.7917 (3.0); 6.7800 (2.9); 6.7693 (1.0); 4.2949 (3.5); 4.2514 (6.0); 4.1728 (6.3); 4.1294 (3.4); 3.3326 (111.5); 2.9159 (15.0); 2.9044 (14.4); 2.8197 (0.7); 2.8030 (1.8); 2.7860 (2.4); 2.7687 (1.8); 2.7519 (0.8); 2.6717 (0.7); 2.5068 (88.4); 2.5027 (110.4); 2.4985 (82.7); 2.3296 (0.7); 1.2386 (0.4); 1.2213 (0.5); 1.2052 (0.5); 1.1875 (1.0); 1.1663 (12.7); 1.1486 (16.0); 1.1449 (15.7); 1.1271 (12.2); 1.1082 (0.7); 1.0835 (0.6); 1.0742 (0.3); 1.0645 (0.3); −0.0002 (16.1) I-111 [00235]
I-111: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 8.2847 (11.5); 7.7937 (0.4); 7.7685 (0.5); 7.7462 (8.6); 7.7412 (3.4); 7.7289 (4.0); 7.7239 (11.1); 7.7159 (1.6); 7.6714 (0.4); 7.6430 (7.7); 7.6191 (7.7); 7.5768 (7.4); 7.5557 (6.0); 7.5301 (1.8); 7.5265 (2.1); 7.5105 (5.3); 7.5070 (5.1); 7.4973 (3.1); 7.4947 (3.0); 7.4772 (3.8); 7.4604 (1.5); 7.4573 (1.5); 7.3611 (1.8); 7.3570 (1.7); 7.3412 (3.7); 7.3378 (3.3); 7.3240 (2.4); 7.3201 (2.4); 7.2856 (5.3); 7.2663 (3.1); 6.8723 (2.9); 6.8609 (2.9); 6.8500 (1.0); 4.2718 (3.7); 4.2282 (6.5); 4.1485 (7.2); 4.1049 (4.0); 3.3285 (38.4); 2.9222 (16.0); 2.9107 (15.8); 2.8174 (0.8); 2.8005 (1.9); 2.7835 (2.6); 2.7664 (2.0); 2.7492 (0.8); 2.6760 (0.6); 2.6719 (0.8); 2.6678 (0.6); 2.5072 (102.6); 2.5029 (129.2); 2.4986 (95.1); 2.3340 (0.6); 2.3295 (0.8); 2.3255 (0.6); 1.2386 (0.6); 1.2214 (0.6); 1.2026 (0.5); 1.1976 (0.5); 1.1681 (14.1); 1.1509 (15.1); 1.1423 (14.8); 1.1251 (13.6); 1.0855 (0.4); 1.0569 (0.5); −0.0002 (23.5); −0.0081 (1.1) I-112 [00236]
I-112: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 8.3693 (6.6); 8.0461 (3.2); 8.0259 (4.0); 7.8666 (4.1); 7.8630 (4.4); 7.8034 (2.5); 7.7998 (2.2); 7.7828 (2.1); 7.7792 (1.9); 7.7565 (0.6); 7.7483 (5.4); 7.7429 (2.1); 7.7313 (2.2); 7.7257 (7.2); 7.7176 (0.9); 7.5723 (4.2); 7.5514 (3.5); 7.5251 (1.1); 7.5216 (1.4); 7.5058 (2.9); 7.5020 (2.9); 7.4909 (1.6); 7.4878 (1.6); 7.4732 (2.0); 7.4705 (2.1); 7.4540 (0.9); 7.4506 (0.9); 7.3578 (1.1); 7.3534 (1.2); 7.3381 (2.2); 7.3340 (2.0); 7.3206 (1.5); 7.3165 (1.5); 7.2811 (2.9); 7.2783 (2.9); 7.2616 (1.8); 7.2584 (1.6); 6.8133 (0.6); 6.8024 (1.6); 6.7908 (1.6); 6.7794 (0.6); 4.2961 (2.3); 4.2527 (3.8); 4.1723 (4.2); 4.1289 (2.3); 4.0560 (1.2); 4.0382 (3.7); 4.0204 (3.7); 4.0026 (1.2); 3.3295 (27.6); 2.9275 (0.4); 2.9082 (10.1); 2.8966 (10.0); 2.8228 (0.4); 2.8054 (1.2); 2.7883 (1.6); 2.7710 (1.2); 2.7541 (0.5); 2.6712 (0.4); 2.5248 (1.1); 2.5112 (25.3); 2.5069 (50.4); 2.5024 (65.3); 2.4979 (47.3); 2.4935 (23.2); 2.3291 (0.4); 1.9892 (16.0); 1.3971 (3.3); 1.1930 (4.7); 1.1752 (10.3); 1.1682 (8.6); 1.1574 (6.7); 1.1510 (9.6); 1.1452 (9.2); 1.1279 (7.8); −0.0002 (2.0) I-113 [00237]
I-113: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 10.0464 (1.4); 8.6165 (5.6); 8.2063 (0.9); 8.1857 (1.2); 8.1432 (3.8); 8.1223 (5.2); 8.0064 (1.2); 7.9852 (1.4); 7.9770 (4.2); 7.9561 (3.4); 7.7581 (5.1); 7.7527 (1.9); 7.7403 (2.9); 7.7356 (6.5); 7.7276 (0.9); 7.5787 (1.3); 7.5691 (3.8); 7.5483 (3.2); 7.2960 (0.4); 7.2928 (0.4); 7.2773 (0.5); 7.2736 (0.5); 7.2428 (1.6); 7.2267 (1.9); 7.2239 (1.9); 7.1382 (0.8); 7.1347 (1.2); 7.1195 (1.9); 7.1160 (2.1); 7.1006 (1.4); 7.0969 (1.3); 7.0915 (0.4); 7.0875 (0.4); 7.0725 (0.4); 7.0688 (0.4); 7.0528 (1.3); 7.0497 (1.4); 7.0339 (1.8); 7.0309 (1.8); 7.0152 (0.7); 7.0124 (0.7); 6.8167 (0.3); 6.8054 (0.6); 6.7945 (1.5); 6.7828 (1.5); 6.7717 (0.5); 6.7150 (2.1); 6.7117 (2.3); 6.7062 (0.7); 6.6956 (2.0); 6.6923 (2.1); 5.7641 (1.5); 5.7562 (16.0); 3.3287 (64.9); 3.2073 (1.1); 3.1945 (2.1); 3.1884 (1.8); 3.1788 (1.8); 3.1233 (1.2); 3.1164 (2.0); 3.1010 (2.2); 3.0890 (1.1); 3.0756 (0.4); 3.0612 (0.7); 3.0551 (0.5); 3.0451 (0.6); 3.0379 (0.3); 2.9891 (0.4); 2.9822 (0.8); 2.9660 (1.0); 2.9479 (0.7); 2.9343 (9.2); 2.9280 (4.3); 2.9227 (9.0); 2.8766 (0.5); 2.8598 (1.0); 2.8425 (1.4); 2.8253 (1.0); 2.8078 (0.4); 2.6758 (0.5); 2.6712 (0.7); 2.6667 (0.5); 2.5247 (1.9); 2.5199 (3.1); 2.5112 (40.6); 2.5068 (82.1); 2.5023 (107.0); 2.4977 (77.0); 2.4933 (37.1); 2.3336 (0.5); 2.3292 (0.6); 2.3247 (0.4); 1.1728 (0.3); 1.1550 (0.4); 1.1450 (4.4); 1.1277 (4.4); 1.1026 (15.3); 1.0854 (15.0); −0.0002 (1.7) I-114 [00238]
I-114: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 12.0149 (3.8); 10.1382 (3.4); 8.5943 (5.1); 8.5483 (1.3); 8.5274 (1.4); 8.0104 (4.6); 8.0066 (4.6); 7.8963 (2.1); 7.8937 (1.9); 7.8756 (1.9); 7.8729 (1.9); 7.7576 (0.7); 7.7494 (5.2); 7.7439 (2.0); 7.7323 (2.3); 7.7268 (6.8); 7.7188 (0.8); 7.5710 (4.1); 7.5502 (3.3); 7.3815 (1.4); 7.3784 (1.4); 7.3595 (2.7); 7.3310 (1.2); 7.3269 (1.3); 7.3100 (2.1); 7.2949 (1.0); 7.2904 (1.0); 7.2533 (1.0); 7.2494 (1.0); 7.2337 (2.3); 7.2301 (2.3); 7.2166 (2.0); 7.2092 (3.5); 7.2051 (3.2); 7.1896 (1.5); 6.8384 (0.6); 6.8280 (1.7); 6.8164 (1.6); 6.8058 (0.5); 4.0374 (1.0); 4.0196 (1.0); 4.0019 (0.3); 3.3397 (74.2); 3.1556 (0.4); 3.1387 (1.1); 3.1217 (1.5); 3.1045 (1.2); 3.0871 (0.5); 2.9276 (9.1); 2.9160 (9.0); 2.6767 (0.4); 2.6721 (0.5); 2.6677 (0.4); 2.5255 (1.8); 2.5118 (33.8); 2.5076 (64.5); 2.5031 (82.6); 2.4986 (61.8); 2.4943 (31.3); 2.3346 (0.4); 2.3299 (0.5); 2.3254 (0.4); 1.9936 (1.2); 1.9897 (4.4); 1.9821 (1.0); 1.3971 (16.0); 1.1962 (15.7); 1.1790 (16.0); 1.1672 (2.3); 1.1573 (3.0); 1.1498 (1.3); 1.1401 (1.6); 0.8882 (0.3) I-115 [00239]
I-115: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 8.4756 (4.5); 8.0883 (1.6); 8.0767 (0.4); 8.0669 (3.0); 8.0184 (2.2); 8.0128 (3.8); 8.0088 (3.1); 8.0011 (1.3); 7.7600 (0.4); 7.7517 (3.4); 7.7465 (1.2); 7.7347 (1.4); 7.7293 (4.4); 7.7213 (0.5); 7.5723 (2.7); 7.5514 (2.2); 7.5356 (0.7); 7.5315 (0.8); 7.5157 (1.9); 7.5119 (1.9); 7.5031 (1.1); 7.5001 (1.1); 7.4856 (1.4); 7.4828 (1.4); 7.4662 (0.6); 7.4630 (0.6); 7.3678 (0.6); 7.3635 (0.7); 7.3481 (1.3); 7.3441 (1.3); 7.3307 (0.9); 7.3266 (0.9); 7.2899 (1.9); 7.2872 (1.9); 7.2705 (1.2); 7.2674 (1.1); 6.8520 (0.4); 6.8409 (1.1); 6.8293 (1.1); 6.8182 (0.4); 4.3063 (1.5); 4.2629 (2.5); 4.1816 (2.7); 4.1381 (1.5); 4.0559 (0.3); 4.0381 (1.0); 4.0203 (1.0); 4.0025 (0.3); 3.5685 (0.3); 3.3304 (62.1); 2.9274 (5.9); 2.9158 (5.9); 2.7997 (0.7); 2.7827 (1.0); 2.7655 (0.8); 2.6717 (0.4); 2.5251 (1.3); 2.5115 (24.2); 2.5072 (47.3); 2.5028 (61.7); 2.4982 (45.8); 2.4940 (23.0); 2.3295 (0.4); 1.9893 (4.4); 1.3974 (16.0); 1.1931 (1.2); 1.1753 (2.8); 1.1658 (5.1); 1.1575 (2.3); 1.1483 (6.4); 1.1447 (6.3); 1.1272 (5.0); 1.1066 (0.4); 0.0077 (0.5); −0.0002 (11.9); −0.0084 (0.5) I-116 [00240]
I-116: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 10.3521 (2.2); 9.9799 (1.9); 7.9111 (1.9); 7.8893 (2.6); 7.7868 (2.5); 7.7649 (2.0); 7.7536 (0.7); 7.7456 (3.4); 7.7402 (1.4); 7.7285 (1.7); 7.7230 (4.6); 7.7151 (0.6); 7.5969 (3.0); 7.5759 (2.3); 7.5321 (0.9); 7.5142 (1.6); 7.4842 (0.7); 7.4662 (1.1); 7.4465 (0.5); 7.3622 (0.6); 7.3590 (0.6); 7.3426 (1.2); 7.3249 (0.7); 7.2740 (1.6); 7.2546 (1.0); 5.7561 (16.0); 4.2463 (1.0); 4.2012 (1.7); 4.1120 (1.9); 4.0670 (1.1); 4.0019 (1.0); 3.9843 (3.2); 3.9666 (3.2); 3.9549 (0.7); 3.9489 (1.1); 3.9372 (1.5); 3.9195 (1.5); 3.9018 (0.5); 3.3286 (11.3); 2.7376 (0.7); 2.7204 (1.0); 2.7033 (0.7); 2.5250 (0.7); 2.5115 (16.1); 2.5071 (32.0); 2.5025 (41.5); 2.4980 (30.4); 2.4936 (14.9); 1.2335 (0.6); 1.2010 (3.5); 1.1841 (3.5); 1.1570 (1.7); 1.1393 (3.4); 1.1264 (5.0); 1.1217 (3.0); 1.1094 (4.9); 1.0468 (2.8); 1.0290 (5.6); 1.0114 (2.7); −0.0002 (0.9) I-117 [00241]
I-117: .sup.1H-NMR(600.1 MHz, CDCl3): δ = 8.0539 (6.8); 8.0400 (7.5); 8.0304 (8.6); 7.7568 (0.6); 7.7428 (0.7); 7.6918 (7.2); 7.6779 (6.7); 7.6162 (0.7); 7.6108 (7.6); 7.6074 (2.5); 7.5995 (2.5); 7.5960 (8.8); 7.5907 (0.9); 7.5647 (0.6); 7.5506 (0.6); 7.4034 (0.8); 7.3790 (2.2); 7.3769 (2.6); 7.3644 (8.2); 7.3504 (4.5); 7.3283 (1.6); 7.3269 (1.6); 7.3151 (2.9); 7.3034 (1.5); 7.2592 (11.1); 7.2540 (1.5); 7.2436 (2.7); 7.2412 (2.6); 7.2314 (1.5); 7.2289 (1.4); 7.1754 (3.4); 7.1735 (3.3); 7.1624 (2.5); 7.1606 (2.3); 4.2955 (0.7); 4.2875 (1.9); 4.2792 (2.0); 4.2711 (0.8); 3.7529 (0.5); 3.7433 (0.9); 3.7324 (1.1); 3.7226 (1.0); 3.7121 (0.7); 3.5351 (0.7); 3.5262 (1.1); 3.5167 (0.9); 3.5052 (0.9); 3.4965 (0.5); 3.1319 (1.8); 3.1244 (15.6); 3.1161 (14.9); 3.1075 (2.3); 3.1018 (2.2); 3.0959 (2.9); 3.0914 (2.5); 3.0841 (3.3); 3.0733 (2.0); 3.0620 (0.5); 2.3527 (1.1); 2.3433 (3.0); 2.3334 (3.9); 2.3242 (2.4); 2.3143 (0.6); 1.5975 (9.7); 1.2290 (16.0); 1.2175 (15.3); 1.0880 (0.9); 1.0767 (0.9); 0.0053 (0.3); −0.0001 (9.8); −0.0056 (0.3); I-118 [00242]
I-118: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 9.1659 (4.7); 9.1640 (4.9); 9.1608 (4.9); 9.1588 (4.7); 9.1519 (0.8); 9.1499 (0.9); 9.1467 (0.8); 9.1446 (0.8); 8.4002 (2.7); 8.3950 (2.5); 8.3796 (3.0); 8.3753 (3.0); 8.3164 (0.5); 8.1943 (11.4); 8.0727 (4.5); 8.0714 (4.5); 8.0522 (4.1); 8.0506 (4.2); 7.8881 (2.2); 7.8683 (0.8); 7.8662 (0.8); 7.8091 (0.5); 7.8039 (0.5); 7.7883 (0.3); 7.7819 (0.4); 7.7622 (0.8); 7.7539 (8.8); 7.7484 (2.9); 7.7369 (4.3); 7.7314 (12.0); 7.7232 (1.2); 7.7198 (0.7); 7.7139 (1.7); 7.5876 (1.6); 7.5768 (7.2); 7.5562 (5.6); 7.5359 (1.4); 7.5318 (1.8); 7.5161 (4.2); 7.5121 (4.2); 7.5025 (2.4); 7.4991 (2.4); 7.4850 (2.8); 7.4819 (3.0); 7.4655 (1.2); 7.4620 (1.2); 7.4271 (0.4); 7.4208 (0.4); 7.3718 (0.8); 7.3667 (1.7); 7.3622 (1.6); 7.3469 (3.1); 7.3426 (3.0); 7.3296 (2.2); 7.3253 (2.2); 7.2927 (4.4); 7.2897 (4.3); 7.2732 (2.6); 7.2700 (2.3); 6.8625 (0.8); 6.8516 (2.7); 6.8400 (2.7); 5.7555 (4.5); 4.3570 (0.6); 4.3102 (4.2); 4.2667 (6.4); 4.2148 (1.0); 4.1895 (6.8); 4.1713 (0.7); 4.1460 (3.8); 3.3261 (127.8); 2.9359 (15.3); 2.9243 (16.0); 2.9104 (2.4); 2.8218 (0.5); 2.8166 (0.7); 2.7994 (1.7); 2.7823 (2.3); 2.7651 (1.8); 2.7480 (0.7); 2.6803 (0.5); 2.6760 (1.1); 2.6713 (1.5); 2.6667 (1.1); 2.6621 (0.5); 2.5249 (4.6); 2.5201 (7.2); 2.5115 (89.6); 2.5070 (184.4); 2.5024 (240.5); 2.4978 (166.9); 2.4932 (76.5); 2.3383 (0.5); 2.3338 (1.0); 2.3292 (1.4); 2.3246 (1.0); 2.3201 (0.4); 1.3517 (0.4); 1.3369 (0.5); 1.2327 (1.7); 1.2253 (1.2); 1.1730 (12.2); 1.1558 (12.2); 1.1415 (13.6); 1.1244 (13.1); 1.0817 (1.9); 1.0646 (1.8); 0.1458 (2.5); 0.0258 (0.3); 0.0079 (22.8); −0.0001 (594.5); −0.0086 (19.4); −0.0236 (0.6); −0.1496 (2.4) I-119 [00243]
I-119: .sup.1H-NMR(400 MHz, d.sub.6-DMSO): δ = 11.8325 (1.9); 9.9870 (1.8); 8.1430 (2.3); 8.0339 (1.4); 8.0136 (1.7); 7.8709 (1.4); 7.7579 (2.7); 7.7525 (1.1); 7.7410 (1.9); 7.7354 (3.6); 7.7236 (0.8); 7.5675 (2.0); 7.5467 (1.6); 7.3772 (0.7); 7.3582 (1.4); 7.3258 (0.5); 7.3165 (0.7); 7.3046 (0.7); 7.2959 (0.5); 7.2851 (0.4); 7.2321 (2.6); 7.2228 (2.2); 6.7403 (0.8); 6.7285 (0.8); 4.0555 (0.4); 4.0376 (1.4); 4.0198 (1.4); 4.0021 (0.5); 3.3337 (31.4); 3.1527 (0.5); 3.1356 (0.7); 3.1185 (0.5); 2.9218 (4.7); 2.9102 (4.6); 2.6697 (6.9); 2.5249 (0.9); 2.5114 (17.2); 2.5070 (33.2); 2.5025 (42.8); 2.4980 (31.6); 2.4936 (15.6); 1.9893 (6.2); 1.3975 (16.0); 1.2068 (7.5); 1.1897 (7.6); 1.1751 (3.6); 1.1573 (1.7); 0.0079 (1.1); −0.0002 (27.9); −0.0085 (1.1) I-120 [00244]
I-120: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 12.0365 (4.1); 10.2264 (3.6); 8.1139 (4.4); 7.8817 (3.5); 7.8593 (3.4); 7.7301 (5.1); 7.7078 (6.7); 7.5677 (4.6); 7.5465 (3.6); 7.3842 (1.6); 7.3649 (2.8); 7.3346 (1.4); 7.3172 (2.2); 7.2971 (1.2); 7.2544 (1.1); 7.2508 (1.2); 7.2348 (2.2); 7.2318 (2.2); 7.2170 (1.3); 7.2137 (1.3); 7.1742 (2.9); 7.1565 (1.8); 6.8353 (0.7); 6.8244 (1.8); 6.8127 (1.8); 6.8018 (0.6); 4.0553 (0.9); 4.0375 (2.6); 4.0197 (2.7); 4.0019 (0.9); 3.3323 (64.6); 3.1509 (0.4); 3.1342 (1.1); 3.1171 (1.5); 3.0998 (1.2); 3.0829 (0.5); 2.9165 (0.5); 2.9052 (0.7); 2.8939 (0.3); 2.8708 (9.5); 2.8593 (9.4); 2.6758 (0.6); 2.6713 (0.7); 2.5066 (89.9); 2.5024 (113.8); 2.4981 (87.1); 2.3293 (0.7); 2.0117 (0.4); 1.9892 (11.0); 1.3973 (1.5); 1.2350 (0.5); 1.1975 (15.9); 1.1804 (16.0); 1.1753 (10.1); 1.1572 (3.5); 1.1495 (1.1); 0.8884 (0.5); 0.8713 (0.5); −0.0003 (39.3) I-121 [00245]
I-121: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 8.3015 (7.5); 8.0620 (3.2); 8.0418 (3.8); 7.7652 (0.8); 7.7569 (6.2); 7.7513 (2.2); 7.7399 (2.4); 7.7342 (8.0); 7.7261 (0.8); 7.6631 (2.1); 7.6423 (2.2); 7.6251 (4.0); 7.5687 (4.4); 7.5481 (3.6); 7.5253 (1.1); 7.5213 (1.3); 7.5055 (3.1); 7.5017 (3.0); 7.4908 (1.7); 7.4876 (1.7); 7.4732 (2.1); 7.4703 (2.2); 7.4537 (0.9); 7.4504 (0.9); 7.3577 (1.2); 7.3532 (1.2); 7.3379 (2.2); 7.3337 (2.1); 7.3205 (1.6); 7.3163 (1.6); 7.2774 (3.1); 7.2745 (3.1); 7.2579 (2.0); 7.2548 (1.8); 6.7622 (0.6); 6.7517 (1.8); 6.7400 (1.8); 6.7289 (0.6); 4.2771 (2.7); 4.2337 (4.4); 4.1597 (4.7); 4.1164 (2.6); 3.3336 (53.0); 2.9199 (11.1); 2.9083 (11.0); 2.8231 (0.5); 2.8063 (1.2); 2.7892 (1.6); 2.7721 (1.2); 2.7551 (0.5); 2.6760 (0.6); 2.6714 (0.8); 2.6540 (16.0); 2.5249 (1.6); 2.5201 (2.7); 2.5115 (32.3); 2.5071 (64.8); 2.5025 (84.8); 2.4979 (62.3); 2.4934 (30.4); 2.3341 (0.5); 2.3294 (0.5); 2.3248 (0.4); 1.9893 (0.7); 1.3973 (2.2); 1.2326 (1.2); 1.1928 (0.3); 1.1693 (8.5); 1.1521 (9.1); 1.1439 (8.9); 1.1267 (8.2); 0.0079 (1.6); −0.0002 (41.7); −0.0085 (1.4) I-122 [00246]
I-122: .sup.1H-NMR(600.1 MHz, d.sub.6-DMSO): δ = 8.3792 (7.2); 8.3634 (0.4); 7.7334 (0.9); 7.7279 (8.7); 7.7242 (2.9); 7.7167 (3.5); 7.7129 (10.8); 7.7073 (1.1); 7.7046 (0.5); 7.6895 (0.4); 7.5616 (5.5); 7.5478 (4.7); 7.5407 (1.0); 7.5312 (6.1); 7.5171 (8.5); 7.5065 (4.4); 7.5040 (4.0); 7.4854 (2.0); 7.4832 (2.1); 7.4731 (2.8); 7.4714 (3.0); 7.4603 (1.4); 7.4581 (1.4); 7.3494 (1.7); 7.3468 (1.7); 7.3364 (3.1); 7.3337 (3.0); 7.3244 (2.2); 7.3217 (2.2); 7.2758 (3.9); 7.2737 (4.0); 7.2627 (2.8); 7.2606 (2.7); 6.8346 (0.8); 6.8271 (2.5); 6.8193 (2.5); 6.8115 (0.8); 5.7533 (7.3); 4.3019 (4.5); 4.2729 (5.8); 4.1782 (6.5); 4.1678 (0.5); 4.1493 (4.4); 4.0359 (0.4); 4.0240 (0.4); 3.9728 (0.4); 3.3212 (89.2); 2.9152 (0.8); 2.9075 (0.8); 2.8711 (15.9); 2.8634 (16.0); 2.8523 (0.7); 2.8445 (0.6); 2.8099 (0.7); 2.7986 (1.7); 2.7872 (2.4); 2.7811 (0.6); 2.7758 (1.8); 2.7643 (0.7); 2.6141 (0.4); 2.5231 (0.8); 2.5200 (1.0); 2.5169 (0.9); 2.5081 (18.5); 2.5051 (41.4); 2.5020 (58.4); 2.4990 (41.9); 2.4959 (19.1); 2.3858 (0.4); 2.0110 (0.5); 1.9887 (1.6); 1.2343 (0.4); 1.1874 (0.6); 1.1756 (1.1); 1.1629 (12.5); 1.1514 (12.5); 1.1435 (12.4); 1.1378 (2.2); 1.1321 (12.2); 1.0869 (0.5); 1.0827 (0.3); 1.0756 (0.5); 0.8860 (0.6); 0.8747 (0.6); −0.0001 (6.2) I-123 [00247]
I-123: .sup.1H-NMR(600.1 MHz, d.sub.6-DMSO): δ = 11.9825 (4.0); 10.1937 (3.4); 8.6820 (1.9); 8.1800 (4.5); 8.1699 (2.6); 8.1561 (4.0); 8.1126 (1.6); 8.1102 (1.6); 8.0987 (1.1); 8.0963 (1.1); 7.7711 (0.5); 7.7656 (5.5); 7.7619 (1.8); 7.7543 (1.9); 7.7505 (6.8); 7.7449 (0.7); 7.5937 (3.5); 7.5796 (3.0); 7.4041 (0.4); 7.3994 (0.5); 7.3865 (1.5); 7.3841 (1.8); 7.3735 (2.3); 7.3712 (2.3); 7.3560 (0.3); 7.3330 (1.2); 7.3310 (1.2); 7.3189 (1.9); 7.3082 (1.0); 7.3059 (1.1); 7.2929 (0.4); 7.2908 (0.4); 7.2801 (0.5); 7.2778 (0.5); 7.2522 (1.0); 7.2498 (1.0); 7.2394 (1.9); 7.2370 (1.9); 7.2273 (1.3); 7.2248 (1.3); 7.2059 (0.4); 7.1991 (2.6); 7.1974 (2.7); 7.1863 (1.5); 7.1844 (1.5); 7.1617 (0.4); 7.1491 (0.4); 7.1465 (0.4); 6.9124 (0.6); 6.9049 (1.8); 6.8971 (1.8); 6.8894 (0.5); 5.7531 (4.4); 4.0360 (0.8); 4.0241 (0.8); 3.3225 (19.6); 3.1586 (0.4); 3.1472 (1.1); 3.1358 (1.5); 3.1243 (1.2); 3.1127 (0.5); 3.0785 (0.3); 2.9428 (9.9); 2.9351 (9.9); 2.9229 (0.3); 2.7231 (0.4); 2.7154 (0.4); 2.5204 (0.4); 2.5173 (0.4); 2.5085 (8.6); 2.5055 (19.1); 2.5025 (26.8); 2.4994 (19.2); 2.4964 (8.7); 2.0112 (0.6); 1.9889 (3.3); 1.3312 (1.7); 1.3029 (1.7); 1.2067 (15.9); 1.1952 (16.0); 1.1879 (1.7); 1.1759 (2.9); 1.1729 (1.3); 1.1664 (4.3); 1.1615 (1.5); 1.1550 (3.8); 1.1463 (0.4); 1.1373 (0.4); 1.1349 (0.4); 0.8861 (0.8); 0.8749 (0.7); −0.0001 (2.6) I-124 [00248]
I-124: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 9.3534 (1.0); 8.4414 (0.5); 8.4154 (11.0); 8.3154 (0.4); 8.2727 (0.4); 8.2692 (0.3); 8.2319 (4.2); 8.2112 (6.7); 8.1667 (5.8); 8.1630 (6.9); 8.1452 (4.7); 8.1412 (3.5); 8.1243 (3.0); 8.1203 (2.5); 8.0698 (0.7); 8.0526 (0.3); 8.0472 (0.9); 7.9999 (0.6); 7.9781 (0.7); 7.9706 (0.4); 7.9467 (0.5); 7.8937 (0.6); 7.7735 (1.0); 7.7655 (8.6); 7.7600 (3.1); 7.7484 (3.9); 7.7429 (11.8); 7.7348 (1.4); 7.7246 (0.8); 7.6013 (7.1); 7.5805 (5.4); 7.5494 (0.6); 7.5287 (1.8); 7.5247 (2.0); 7.5089 (4.6); 7.5050 (4.6); 7.4943 (2.7); 7.4909 (2.6); 7.4765 (3.2); 7.4736 (3.3); 7.4571 (1.4); 7.4537 (1.4); 7.3726 (0.6); 7.3604 (1.8); 7.3559 (1.9); 7.3406 (3.4); 7.3365 (3.2); 7.3232 (2.4); 7.3190 (2.3); 7.2835 (4.8); 7.2806 (4.6); 7.2640 (2.9); 7.2608 (2.6); 6.9359 (0.9); 6.9251 (2.8); 6.9135 (2.8); 6.9020 (1.0); 5.7553 (0.4); 4.3071 (3.9); 4.2917 (0.4); 4.2637 (6.3); 4.2415 (0.3); 4.1941 (0.6); 4.1825 (6.6); 4.1735 (0.8); 4.1479 (0.5); 4.1391 (3.7); 3.3238 (94.2); 2.9401 (15.1); 2.9286 (15.3); 2.9132 (1.2); 2.8909 (0.6); 2.8189 (0.8); 2.8018 (1.9); 2.7849 (2.6); 2.7677 (1.9); 2.7505 (0.8); 2.7324 (0.6); 2.6757 (1.1); 2.6711 (1.3); 2.6666 (1.0); 2.5245 (3.0); 2.5110 (57.0); 2.5066 (113.8); 2.5020 (153.7); 2.4975 (115.1); 2.4931 (56.1); 2.3380 (0.4); 2.3335 (0.7); 2.3290 (1.0); 2.3244 (0.7); 1.4977 (5.7); 1.1811 (1.0); 1.1664 (12.8); 1.1490 (16.0); 1.1455 (15.6); 1.1280 (12.3); 1.0917 (0.8); 1.0747 (0.7); −0.0002 (7.0) I-125 [00249]
I-125: .sup.1H-NMR(400.2 MHz, CDCl3): δ = 8.6201 (0.6); 8.1034 (1.6); 8.0828 (1.8); 7.7589 (0.8); 7.7398 (0.7);7.6507 (0.3); 7.6420 (2.2); 7.6369 (0.8); 7.6248 (0.9); 7.6197 (2.7); 7.6118 (0.4); 7.3783 (2.0); 7.3562 (1.7); 7.2924 (0.7); 7.2890 (0.8); 7.2637 (17.2); 7.1310 (0.7); 7.1274 (0.7); 7.1125 (0.6); 7.1086 (0.6); 7.0941 (0.6); 7.0906 (0.6); 7.0755 (0.8); 7.0724 (0.8); 6.8363 (0.8); 6.8193 (0.7); 4.5317 (0.4); 4.5210 (0.4); 3.9140 (0.8); 3.8987 (1.5); 3.8833 (0.9); 3.1653 (0.4); 3.1529 (0.4); 3.1447 (0.6); 3.1291 (4.6); 3.1167 (4.2); 2.9343 (1.0); 2.9195 (1.4); 2.9041 (1.2); 2.4288 (0.8); 2.4137 (1.1); 2.3984 (0.7); 2.1732 (8.1); 2.0087 (0.5); 1.6645 (16.0); 1.2568 (7.9); 1.2396 (7.7); 0.0078 (1.1); −0.0002 (24.8); −0.0083 (1.2) I-126 [00250]
I-126: .sup.1H-NMR(400.2 MHz, CDCl3): δ = 8.0604 (5.4); 8.0394 (10.7); 7.9364 (0.8); 7.6993 (5.9); 7.6785 (5.2); 7.6405 (0.8); 7.6325 (5.9); 7.6274 (2.1); 7.6154 (2.3); 7.6102 (7.2); 7.6023 (0.8); 7.4085 (0.4); 7.3804 (5.9); 7.3670 (3.6); 7.3632 (4.6); 7.3581 (4.7); 7.3384 (1.3); 7.3355 (1.4); 7.3177 (2.3); 7.3012 (1.1); 7.2982 (1.1); 7.2607 (33.8); 7.2492 (2.4); 7.2453 (2.2); 7.2311 (1.3); 7.2273 (1.2); 7.1858 (3.0); 7.1829 (2.9); 7.1665 (1.8); 7.1635 (1.7); 5.2998 (1.3); 4.3230 (0.6); 4.3114 (1.6); 4.2989 (1.6); 4.2867 (0.6); 3.7700 (0.4); 3.7560 (0.8); 3.7393 (1.0); 3.7235 (1.0); 3.7089 (0.7); 3.5489 (0.6); 3.5358 (1.1); 3.5220 (0.8); 3.5037 (0.8); 3.4906 (0.4); 3.1375 (11.7); 3.1250 (11.7); 3.1121 (2.1); 3.1057 (3.4); 3.0899 (3.8); 3.0773 (2.6); 3.0609 (0.8); 2.3679 (0.9); 2.3536 (2.5); 2.3392 (3.4); 2.3250 (2.1); 2.3101 (0.6); 2.0076 (0.5); 1.7865 (0.4); 1.7682 (0.4); 1.7308 (0.4); 1.7176 (0.4); 1.3369 (0.6); 1.2787 (0.6); 1.2537 (0.6); 1.2332 (16.0); 1.2160 (15.3); 1.0920 (0.4); 1.0746 (0.5); 0.0077 (2.0); −0.0002 (48.2); −0.0082 (2.2) I-127 [00251]
I-127: .sup.1H-NMR(400.2 MHz, CDCl3): δ = 8.1927 (0.4); 8.1503 (6.6); 8.1023 (0.4); 8.0858 (6.5); 8.0650 (7.2); 7.8682 (0.9); 7.8461 (6.2); 7.8383 (5.9); 7.8162 (0.9); 7.7361 (7.2); 7.7151 (6.5); 7.6485 (0.9); 7.6406 (7.2); 7.6353 (2.8); 7.6250 (5.0); 7.6185 (9.0); 7.6095 (1.9); 7.6033 (3.9); 7.5216 (3.2); 7.5117 (3.4); 7.4778 (5.4); 7.4737 (7.1); 7.4657 (4.5); 7.4597 (3.6); 7.4372 (0.6); 7.4106 (0.5); 7.3854 (7.5); 7.3633 (6.5); 7.3534 (1.6); 7.3415 (2.2); 7.3328 (1.6); 7.3265 (1.3); 7.3212 (2.2); 7.3142 (1.6); 7.3065 (1.4); 7.2993 (1.3); 7.2620 (56.8); 7.2123 (1.7); 7.1929 (1.5); 7.1836 (3.9); 7.1645 (2.7); 5.9203 (2.2); 5.9173 (2.2); 5.8673 (4.7); 5.8645 (4.5); 4.3146 (2.0); 4.3011 (2.4); 4.2881 (1.4); 3.1480 (15.9); 3.1355 (15.7); 2.8955 (0.3); 2.8781 (0.9); 2.8666 (1.7); 2.8612 (1.4); 2.8495 (2.3); 2.8324 (1.6); 2.8156 (0.7); 1.8749 (8.0); 1.8723 (7.6); 1.7987 (16.0); 1.5854 (36.4); 1.4253 (0.9); 1.3373 (0.3); 1.2794 (0.5); 1.2552 (12.0); 1.2382 (11.2); 1.2225 (1.0); 1.1931 (12.9); 1.1758 (12.8); 1.1582 (5.6); 1.1412 (5.3); 0.1463 (0.4); 0.0079 (3.7); −0.0002 (88.6); −0.0083 (4.1); −0.1493 (0.4) I-128 [00252]
I-128: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 9.9123 (5.4); 7.8579 (5.2); 7.8361 (7.4); 7.7312 (7.2); 7.7185 (10.5); 7.7129 (6.5); 7.7096 (6.4); 7.7018 (4.6); 7.6960 (12.6); 7.6879 (1.6); 7.5529 (8.4); 7.5307 (8.7); 7.5119 (4.2); 7.5090 (4.3); 7.4817 (2.0); 7.4640 (3.0); 7.4443 (1.3); 7.3602 (1.5); 7.3567 (1.5); 7.3404 (3.0); 7.3378 (2.9); 7.3227 (1.8); 7.3193 (1.8); 7.2685 (4.0); 7.2661 (4.1); 7.2490 (2.7); 7.2464 (2.5); 6.7983 (1.6); 6.7847 (3.3); 6.7720 (1.6); 4.2409 (2.9); 4.1959 (4.8); 4.1077 (5.4); 4.0627 (3.1); 4.0562 (1.6); 4.0383 (3.6); 4.0205 (3.6); 4.0027 (1.2); 3.7937 (0.5); 3.7771 (0.5); 3.5620 (1.4); 3.5561 (1.9); 3.5425 (8.3); 3.5312 (7.7); 3.5186 (3.9); 3.5073 (5.8); 3.4939 (3.8); 3.3293 (41.3); 3.2786 (41.0); 2.7528 (0.7); 2.7360 (1.9); 2.7189 (2.7); 2.7018 (2.0); 2.6848 (0.8); 2.6756 (0.5); 2.6708 (0.6); 2.6665 (0.5); 2.5243 (2.1); 2.5196 (3.0); 2.5110 (31.1); 2.5065 (63.6); 2.5020 (84.0); 2.4974 (61.6); 2.4929 (31.2); 2.3333 (0.4); 2.3288 (0.5); 2.3243 (0.4); 2.0114 (1.5); 1.9999 (0.6); 1.9891 (16.0); 1.2987 (0.4); 1.2586 (0.6); 1.2315 (0.8); 1.1998 (9.3); 1.1931 (7.6); 1.1828 (9.3); 1.1754 (10.7); 1.1575 (4.6); 1.1258 (12.3); 1.1088 (12.1); 0.8885 (1.7); 0.8784 (0.4); 0.8717 (1.7); 0.1458 (0.3); 0.0145 (0.4); 0.0079 (2.6); −0.0002 (76.5); −0.0085 (3.5) I-129 [00253]
I-129: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 8.3446 (12.3); 8.3161 (0.7); 8.0374 (8.9); 8.0165 (11.2); 7.8150 (10.6); 7.7940 (8.9); 7.7404 (9.8); 7.7354 (3.9); 7.7232 (4.2); 7.7180 (12.7); 7.7101 (1.5); 7.5745 (9.7); 7.5524 (7.7); 7.5206 (2.4); 7.5045 (5.6); 7.5011 (5.5); 7.4899 (3.1); 7.4873 (3.1); 7.4698 (4.0); 7.4529 (1.6); 7.4501 (1.6); 7.3569 (1.9); 7.3526 (1.9); 7.3371 (3.9); 7.3334 (3.6); 7.3197 (2.6); 7.3157 (2.5); 7.2758 (5.6); 7.2734 (5.6); 7.2564 (3.4); 7.2537 (3.2); 6.8930 (2.0); 6.8798 (3.9); 6.8675 (1.9); 4.2782 (4.3); 4.2349 (7.4); 4.1613 (7.8); 4.1179 (4.1); 3.5732 (1.4); 3.5666 (2.4); 3.5531 (9.5); 3.5427 (10.2); 3.5250 (6.8); 3.5118 (4.3); 3.4578 (0.3); 3.3263 (113.4); 3.2844 (52.6); 2.8224 (0.9); 2.8057 (2.2); 2.7887 (3.0); 2.7716 (2.2); 2.7546 (0.9); 2.6754 (1.6); 2.6711 (2.1); 2.6666 (1.5); 2.5064 (258.3); 2.5021 (326.3); 2.4977 (239.2); 2.3331 (1.6); 2.3288 (2.1); 2.3246 (1.6); 1.1694 (15.0); 1.1522 (16.0); 1.1432 (15.8); 1.1260 (14.4); 0.1459 (1.0); 0.0076 (10.8); −0.0003 (212.4); −0.0084 (9.9); −0.1498 (1.0) I-130 [00254]
I-130: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 8.3660 (4.6); 8.0416 (3.4); 8.0207 (4.3); 7.8199 (4.1); 7.7989 (3.5); 7.7421 (3.7); 7.7370 (1.6); 7.7248 (1.8); 7.7197 (4.8); 7.5748 (3.7); 7.5528 (3.0); 7.4085 (2.3); 7.3866 (2.6); 7.0696 (1.4); 7.0627 (1.6); 7.0477 (1.3); 7.0409 (1.4); 6.8893 (3.8); 6.8824 (4.5); 4.2637 (1.7); 4.2204 (2.6); 4.1265 (2.7); 4.0833 (1.6); 3.7568 (16.0); 3.5684 (1.0); 3.5548 (3.8); 3.5445 (4.2); 3.5273 (2.8); 3.5140 (1.8); 3.3286 (17.0); 3.2856 (19.4); 2.7408 (0.3); 2.7243 (0.9); 2.7071 (1.2); 2.6898 (0.9); 2.6718 (0.6); 2.5068 (41.3); 2.5025 (51.9); 2.4982 (39.5); 2.3291 (0.3); 1.1372 (5.6); 1.1201 (5.9); 1.1082 (6.0); 1.0911 (5.5); −0.0002 (31.1) I-131 [00255]
I-131: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 9.9373 (2.2); 7.8559 (2.1); 7.8341 (3.0); 7.7321 (2.9); 7.7171 (4.3); 7.7113 (3.2); 7.7004 (1.7); 7.6947 (4.9); 7.6866 (0.6); 7.5538 (3.3); 7.5316 (2.7); 7.4144 (1.9); 7.3926 (2.2); 7.0594 (1.0); 7.0527 (1.1); 7.0376 (0.9); 7.0309 (1.0); 6.8900 (2.2); 6.8833 (2.0); 6.7980 (0.7); 6.7845 (1.4); 6.7714 (0.7); 4.2290 (1.2); 4.1840 (1.8); 4.0714 (2.1); 4.0265 (1.3); 3.7572 (16.0); 3.5607 (0.6); 3.5552 (0.8); 3.5414 (3.2); 3.5301 (3.0); 3.5170 (1.6); 3.5057 (2.3); 3.4923 (1.5); 3.3268 (77.2); 3.2784 (16.2); 2.6752 (0.8); 2.6708 (1.2); 2.6665 (0.8); 2.6617 (0.5); 2.6533 (0.8); 2.6364 (1.1); 2.6193 (0.8); 2.6020 (0.4); 2.5242 (4.4); 2.5108 (56.9); 2.5064 (111.5); 2.5019 (144.6); 2.4974 (105.1); 2.4930 (52.7); 2.3333 (0.7); 2.3287 (0.9); 2.3242 (0.7); 1.1589 (3.7); 1.1419 (3.7); 1.0944 (5.0); 1.0774 (4.8); 0.1459 (0.5); 0.0079 (4.3); −0.0002 (106.9); −0.0085 (4.9); −0.1497 (0.5) I-132 [00256]
I-132: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 11.8379 (4.2); 10.0349 (3.8); 8.1781 (5.0); 8.0103 (2.1); 7.9886 (9.6); 7.9765 (7.5); 7.9548 (1.8); 7.7525 (0.6); 7.7443 (5.4); 7.7390 (2.0); 7.7274 (2.3); 7.7219 (7.1); 7.7139 (0.8); 7.5732 (5.1); 7.5510 (4.1); 7.3723 (1.5); 7.3536 (3.1); 7.3220 (1.0); 7.3147 (1.2); 7.3076 (1.2); 7.3007 (1.7); 7.2946 (0.8); 7.2892 (0.8); 7.2810 (1.0); 7.2493 (0.5); 7.2459 (0.4); 7.2296 (2.6); 7.2262 (3.2); 7.2221 (3.7); 7.2151 (4.8); 7.2030 (0.5); 6.8884 (1.0); 6.8751 (2.1); 6.8623 (1.0); 3.5774 (0.7); 3.5707 (1.2); 3.5572 (5.2); 3.5472 (5.5); 3.5307 (3.5); 3.5174 (2.2); 3.4981 (0.4); 3.3364 (27.6); 3.2981 (0.5); 3.2866 (30.1); 3.1700 (0.4); 3.1529 (1.1); 3.1357 (1.6); 3.1185 (1.2); 3.1087 (0.3); 3.1013 (0.5); 2.5256 (1.0); 2.5121 (16.9); 2.5078 (32.6); 2.5033 (41.6); 2.4987 (30.4); 2.4943 (15.0); 1.2021 (16.0); 1.1848 (15.7); 1.0753 (0.4); 1.0578 (0.7); 1.0404 (0.4); 0.0078 (1.6); −0.0002 (39.2); −0.0085 (1.6) I-133 [00257]
I-133: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 11.8458 (2.6); 9.9980 (2.3); 8.1739 (3.2); 8.0089 (1.6); 7.9875 (5.6); 7.9694 (4.6); 7.9479 (1.5); 7.7433 (3.4); 7.7380 (1.2); 7.7264 (1.4); 7.7208 (4.5); 7.7128 (0.5); 7.5740 (3.2); 7.5518 (2.6); 7.2619 (2.1); 7.2403 (2.4); 6.9061 (1.2); 6.8993 (1.4); 6.8847 (1.5); 6.8772 (2.2); 6.8623 (0.6); 6.8274 (2.5); 6.8207 (2.1); 3.7450 (16.0); 3.7159 (0.4); 3.5764 (0.4); 3.5694 (0.7); 3.5561 (3.3); 3.5459 (3.4); 3.5291 (2.2); 3.5159 (1.4); 3.3332 (35.9); 3.2861 (19.6); 3.0697 (0.7); 3.0526 (1.0); 3.0355 (0.7); 2.5252 (1.1); 2.5116 (19.2); 2.5074 (38.4); 2.5029 (50.0); 2.4983 (36.8); 2.4939 (18.5); 1.9893 (1.2); 1.1932 (0.5); 1.1729 (10.2); 1.1557 (10.1); 1.1330 (0.5); 1.1158 (0.3); 1.0696 (0.9); 0.0078 (1.5); −0.0002 (41.9); −0.0085 (1.8) I-134 [00258]
I-134: 1H-NMR(400.2 MHz, d6-DMSO): δ = 11.8388 (2.1); 9.9914 (1.9); 8.1734 (2.7); 8.0043 (1.4); 7.9828 (5.0); 7.9659 (4.1); 7.9444 (1.2); 7.7742 (3.2); 7.7687 (1.1); 7.7573 (1.2); 7.7517 (4.0); 7.7435 (0.4); 7.5687 (2.7); 7.5465 (2.3); 7.2619 (1.8); 7.2403 (2.1); 6.9058 (1.0); 6.8989 (1.2); 6.8842 (0.9); 6.8773 (1.1); 6.8293 (2.2); 6.8225 (1.8); 6.7813 (0.6); 6.7676 (1.2); 6.7534 (0.6); 4.7686 (1.0); 4.7545 (2.3); 4.7402 (1.0); 4.3513 (1.7); 4.3408 (1.8); 3.7930 (0.6); 3.7825 (0.6); 3.7777 (0.8); 3.7673 (0.8); 3.7625 (0.7); 3.7518 (1.0); 3.7446 (15.0); 3.6344 (0.7); 3.6190 (2.1); 3.6043 (2.4); 3.5895 (0.9); 3.4497 (0.7); 3.4354 (1.8); 3.4206 (1.6); 3.4055 (0.5); 3.3298 (145.4); 3.3061 (0.3); 3.0681 (0.6); 3.0510 (0.8); 3.0341 (0.6); 2.6757 (0.6); 2.6712 (0.8); 2.6666 (0.5); 2.5247 (2.3); 2.5199 (3.4); 2.5112 (45.7); 2.5068 (94.8); 2.5023 (124.7); 2.4977 (87.9); 2.4931 (41.1); 2.3336 (0.6); 2.3291 (0.8); 2.3244 (0.6); 1.1726 (8.9); 1.1554 (8.8); 1.0688 (0.4); 1.0452 (16.0); 1.0299 (15.8); 0.1459 (0.4); 0.0079 (3.6); −0.0002 (114.0); −0.0086 (3.7); −0.1496 (0.5) I-135 [00259]
I-135: 1H-NMR(400.2 MHz, d6-DMSO): δ = 11.8275 (3.8); 10.0264 (3.5); 8.3155 (0.6); 8.1749 (4.8); 8.0031 (1.8); 7.9813 (9.9); 7.9711 (7.6); 7.9491 (1.6); 7.7820 (0.6); 7.7738 (5.6); 7.7683 (2.0); 7.7569 (2.2); 7.7513 (7.2); 7.7432 (0.7); 7.6702 (0.4); 7.6477 (0.6); 7.5679 (4.8); 7.5455 (4.3); 7.3717 (1.4); 7.3531 (3.0); 7.3210 (1.0); 7.3138 (1.2); 7.3066 (1.2); 7.2997 (1.6); 7.2936 (0.7); 7.2880 (0.8); 7.2801 (1.0); 7.2480 (0.5); 7.2444 (0.4); 7.2283 (2.5); 7.2248 (3.0); 7.2206 (3.4); 7.2139 (4.4); 7.2119 (4.4); 7.2009 (0.5); 6.7803 (1.0); 6.7664 (2.0); 6.7524 (1.0); 4.7674 (1.7); 4.7532 (4.0); 4.7391 (1.8); 4.3502 (0.5); 4.3395 (0.5); 3.9238 (0.4); 3.6339 (1.3); 3.6185 (3.8); 3.6038 (4.3); 3.5891 (1.6); 3.5277 (0.3); 3.5127 (0.4); 3.4491 (1.4); 3.4348 (3.3); 3.4201 (2.9); 3.4052 (1.0); 3.3277 (249.7); 3.2984 (0.6); 3.2832 (0.4); 3.1658 (0.4); 3.1491 (1.1); 3.1320 (1.5); 3.1149 (1.2); 3.0976 (0.4); 2.6800 (0.6); 2.6756 (1.3); 2.6710 (1.7); 2.6665 (1.3); 2.6619 (0.6); 2.5245 (5.4); 2.5198 (8.3); 2.5111 (104.3); 2.5066 (214.6); 2.5021 (281.1); 2.4975 (196.9); 2.4929 (91.2); 2.3380 (0.6); 2.3335 (1.2); 2.3289 (1.7); 2.3243 (1.2); 2.3198 (0.6); 1.9086 (1.1); 1.2004 (16.0); 1.1832 (16.0); 1.1493 (0.4); 1.0686 (2.3); 1.0450 (4.7); 1.0298 (4.6); 0.1459 (1.1); 0.0079 (8.9); −0.0002 (269.4); −0.0086 (8.7); −0.1497 (1.1) I-136 [00260]
I-136: 1H-NMR(400.2 MHz, d6-DMSO): δ = 11.8347 (3.8); 10.0317 (3.5); 8.1783 (4.6); 8.0238 (2.6); 8.0022 (8.4); 7.9830 (6.6); 7.9616 (2.2); 7.7691 (0.7); 7.7606 (5.5); 7.7551 (2.0); 7.7437 (2.2); 7.7381 (7.3); 7.7301 (0.8); 7.6009 (5.0); 7.5787 (4.0); 7.3718 (1.4); 7.3535 (2.9); 7.3217 (1.0); 7.3142 (1.2); 7.3075 (1.2); 7.3004 (1.7); 7.2941 (0.8); 7.2890 (0.8); 7.2806 (1.1); 7.2667 (1.2); 7.2528 (2.3); 7.2387 (1.2); 7.2291 (2.6); 7.2256 (3.1); 7.2217 (3.4); 7.2148 (4.5); 7.2130 (4.3); 7.2024 (0.6); 3.6244 (1.1); 3.6085 (2.8); 3.5939 (2.8); 3.5780 (1.1); 3.3301 (195.4); 3.1676 (0.4); 3.1506 (1.1); 3.1334 (1.5); 3.1162 (1.1); 3.0986 (0.5); 2.9292 (3.3); 2.9130 (6.6); 2.8965 (2.8); 2.6758 (0.7); 2.6713 (1.0); 2.6667 (0.7); 2.5248 (3.1); 2.5200 (4.7); 2.5114 (58.4); 2.5069 (119.2); 2.5024 (155.2); 2.4978 (108.5); 2.4932 (50.4); 2.3384 (0.3); 2.3337 (0.7); 2.3291 (1.0); 2.3246 (0.7); 1.3014 (1.4); 1.2390 (0.7); 1.2218 (0.7); 1.2012 (15.7); 1.1840 (16.0); 1.1674 (1.2); 1.1579 (0.8); 1.1499 (0.5); 1.1409 (1.0); 1.1376 (1.1); 1.1245 (0.5); 1.1204 (0.9); 0.1459 (1.4); 0.0079 (12.0); −0.0002 (312.5); −0.0086 (10.8); −0.1496 (1.4) I-137 [00261]
I-137: 1H-NMR(400.2 MHz, d6-DMSO): δ = 11.8488 (2.2); 9.9975 (2.0); 8.1789 (2.6); 8.0274 (1.8); 8.0059 (4.7); 7.9789 (3.8); 7.9574 (1.6); 7.7624 (3.2); 7.7569 (1.1); 7.7455 (1.3); 7.7398 (4.4); 7.7317 (0.4); 7.6017 (2.8); 7.5794 (2.2); 7.2690 (0.7); 7.2620 (2.2); 7.2557 (1.3); 7.2405 (2.7); 6.9063 (1.1); 6.8994 (1.2); 6.8847 (0.9); 6.8778 (1.2); 6.8327 (2.3); 6.8259 (1.8); 5.7552 (0.4); 3.7460 (16.0); 3.6265 (0.6); 3.6105 (1.5); 3.5959 (1.5); 3.5799 (0.6); 3.5688 (9.1); 3.3276 (11.7); 3.0719 (0.6); 3.0547 (0.8); 3.0375 (0.6); 2.9309 (1.8); 2.9147 (3.8); 2.8982 (1.6); 2.5250 (0.7); 2.5203 (1.0); 2.5116 (13.3); 2.5071 (27.4); 2.5026 (35.8); 2.4979 (25.0); 2.4934 (11.5); 1.1744 (9.1); 1.1572 (8.9); 1.0706 (0.7); 0.1458 (0.4); 0.0079 (3.6); −0.0002 (93.9); −0.0087 (3.1); −0.1497 (0.4) I-138 [00262]
I-138: 1H-NMR(400.2 MHz, d6-DMSO): δ = 8.3423 (12.7); 8.3155 (3.8); 8.1742 (0.5); 8.0325 (9.0); 8.0115 (11.6); 7.9806 (0.9); 7.9709 (0.8); 7.8141 (10.7); 7.7930 (9.2); 7.7803 (1.4); 7.7720 (11.0); 7.7666 (4.0); 7.7550 (4.3); 7.7495 (13.7); 7.7412 (1.6); 7.6696 (0.7); 7.6472 (1.0); 7.5697 (9.7); 7.5474 (8.3); 7.5202 (2.8); 7.5044 (5.4); 7.5006 (5.2); 7.4898 (3.0); 7.4869 (3.1); 7.4692 (3.9); 7.4530 (1.6); 7.4496 (1.7); 7.3568 (2.0); 7.3526 (2.1); 7.3370 (3.9); 7.3331 (3.6); 7.3196 (2.8); 7.3154 (2.6); 7.2992 (0.4); 7.2753 (5.4); 7.2724 (5.4); 7.2561 (3.4); 7.2529 (3.1); 7.2235 (0.4); 7.2130 (0.4); 6.8199 (0.4); 6.7878 (2.1); 6.7743 (4.0); 6.7603 (2.0); 5.7547 (0.3); 4.7598 (3.7); 4.7454 (8.0); 4.7314 (3.5); 4.7075 (0.5); 4.6472 (2.4); 4.6234 (2.0); 4.2771 (4.5); 4.2337 (7.6); 4.1608 (8.1); 4.1413 (0.9); 4.1174 (4.5); 3.6794 (0.3); 3.6701 (4.0); 3.6313 (2.7); 3.6161 (7.5); 3.6012 (8.5); 3.5865 (3.4); 3.5489 (0.3); 3.5277 (0.7); 3.5122 (0.7); 3.4976 (0.4); 3.4458 (2.9); 3.4318 (6.6); 3.4168 (5.9); 3.4019 (2.0); 3.3236 (860.4); 3.2976 (1.5); 3.2838 (0.8); 3.2680 (0.3); 2.8216 (0.9); 2.8042 (2.3); 2.7873 (3.0); 2.7698 (2.3); 2.7535 (0.9); 2.6795 (3.6); 2.6751 (7.8); 2.6706 (10.7); 2.6661 (7.6); 2.6616 (3.8); 2.6013 (0.6); 2.5240 (41.9); 2.5192 (62.2); 2.5106 (657.7); 2.5062 (1329.6); 2.5017 (1731.7); 2.4971 (1220.6); 2.4926 (574.4); 2.3377 (3.5); 2.3330 (7.5); 2.3285 (10.3); 2.3240 (7.6); 2.0971 (4.9); 2.0946 (4.1); 1.2148 (1.1); 1.1971 (2.6); 1.1790 (2.5); 1.1686 (15.1); 1.1514 (16.0); 1.1425 (15.7); 1.1253 (14.7); 1.0834 (0.5); 1.0684 (0.4); 0.1458 (15.6); 0.1370 (0.6); 0.0494 (0.6); 0.0400 (0.8); 0.0318 (2.5); 0.0208 (8.0); 0.0077 (135.4); −0.0002 (3401.8); −0.0087 (121.6); −0.0272 (3.5); −0.0382 (2.5); −0.0775 (0.7); −0.0913 (0.6); −0.1413 (1.0); −0.1498 (15.9) I-139 [00263]
I-139: 1H-NMR(400.2 MHz, d6-DMSO): δ = 9.9899 (0.5); 8.3629 (4.0); 8.3159 (0.7); 8.1734 (0.9); 8.0353 (2.8); 8.0143 (3.7); 8.0042 (0.5); 7.9824 (1.5); 7.9650 (1.2); 7.9433 (0.4); 7.8180 (3.4); 7.7969 (2.8); 7.7816 (0.5); 7.7732 (4.3); 7.7678 (1.6); 7.7563 (1.6); 7.7507 (5.4); 7.7425 (0.6); 7.5700 (3.4); 7.5477 (2.9); 7.4085 (2.0); 7.3866 (2.3); 7.2613 (0.6); 7.2397 (0.6); 7.0695 (1.2); 7.0625 (1.3); 7.0477 (1.1); 7.0407 (1.2); 6.8983 (0.4); 6.8871 (3.0); 6.8802 (2.9); 6.8302 (0.6); 6.8236 (0.6); 6.7890 (0.6); 6.7753 (1.3); 6.7619 (0.7); 5.7551 (3.2); 4.7614 (1.1); 4.7518 (0.9); 4.7471 (2.4); 4.7329 (1.1); 4.6236 (0.5); 4.2621 (1.6); 4.2188 (2.2); 4.1256 (2.4); 4.0824 (1.5); 3.7717 (0.5); 3.7565 (16.0); 3.7444 (4.8); 3.6703 (0.5); 3.6326 (0.9); 3.6174 (2.7); 3.6026 (3.0); 3.5880 (1.2); 3.4479 (1.0); 3.4333 (2.3); 3.4189 (2.1); 3.4038 (0.7); 3.3240 (103.3); 2.7219 (0.6); 2.7048 (0.9); 2.6875 (0.7); 2.6799 (0.6); 2.6753 (1.3); 2.6707 (1.9); 2.6662 (1.2); 2.6618 (0.6); 2.5243 (5.2); 2.5196 (8.0); 2.5109 (97.7); 2.5064 (202.6); 2.5018 (266.6); 2.4972 (186.8); 2.4926 (87.0); 2.3377 (0.6); 2.3332 (1.2); 2.3286 (1.6); 2.3240 (1.2); 2.3194 (0.5); 2.0973 (0.6); 2.0946 (0.9); 1.1971 (0.5); 1.1726 (2.7); 1.1554 (2.7); 1.1361 (4.5); 1.1189 (4.6); 1.1071 (4.7); 1.0899 (4.5); 0.1458 (3.0); 0.0287 (0.4); 0.0079 (28.4); −0.0002 (722.0); −0.0087 (25.0); −0.0192 (1.2); −0.0311 (0.5); −0.0393 (0.4); −0.1497 (3.0) I-140 [00264]
I-140:1H-NMR(400.2 MHz, d6-DMSO): δ = 9.9439 (1.9); 7.8742 (1.9); 7.8523 (2.7); 7.7424 (2.8); 7.7350 (4.2); 7.7294 (1.6); 7.7186 (2.6); 7.7124 (5.2); 7.7043 (0.5); 7.5817 (3.1); 7.5594 (2.4); 7.4144 (1.8); 7.3926 (2.0); 7.1923 (0.7); 7.1787 (1.4); 7.1648 (0.6); 7.0595 (0.9); 7.0528 (1.0); 7.0377 (0.8); 7.0310 (0.9); 6.8902 (2.1); 6.8834 (1.9); 4.2295 (1.1); 4.1846 (1.7); 4.0724 (1.9); 4.0275 (1.2); 3.7578 (16.0); 3.6003 (0.6); 3.5841 (1.7); 3.5694 (1.7); 3.5532 (0.7); 3.3254 (51.4); 2.9172 (1.9); 2.9009 (3.9); 2.8844 (1.7); 2.6751 (0.5); 2.6708 (0.8); 2.6661 (0.5); 2.6543 (0.7); 2.6372 (1.0); 2.6201 (0.7); 2.5243 (1.8); 2.5195 (2.7); 2.5108 (34.4); 2.5063 (71.9); 2.5018 (95.0); 2.4972 (66.9); 2.4926 (31.2); 2.3331 (0.4); 2.3286 (0.6); 2.3241 (0.4); 1.1594 (3.3); 1.1423 (3.2); 1.0951 (4.7); 1.0780 (4.6); 0.1458 (0.5); 0.0079 (4.4); −0.0002 (131.7); −0.0086 (4.1); −0.1498 (0.5) I-141 [00265]
I-141: 1H-NMR{400.2 MHz, d6-DMSO): δ = 8.3502 (13.2); 8.3158 (0.7); 8.0563 (9.2); 8.0354 (12.0); 7.8242 (10.7); 7.8129 (1.0); 7.8031 (9.2); 7.7673 (1.0); 7.7590 (10.8); 7.7534 (4.2); 7.7422 (4.2); 7.7365 (14.8); 7.7284 (1.5); 7.6028 (9.6); 7.5805 (7.6); 7.5250 (1.8); 7.5208 (2.3); 7.5052 (5.3); 7.5011 (5.3); 7.4907 (3.0); 7.4874 (3.0); 7.4731 (3.6); 7.4701 (3.9); 7.4535 (1.6); 7.4502 (1.6); 7.3576 (2.0); 7.3532 (2.0); 7.3379 (3.9); 7.3337 (3.8); 7.3205 (2.8); 7.3162 (2.8); 7.2768 (7.4); 7.2739 (6.6); 7.2633 (4.4); 7.2573 (4.5); 7.2539 (4.1); 7.2495 (2.2); 5.7551 (0.3); 4.2794 (5.0); 4.2361 (7.8); 4.1626 (8.4); 4.1193 (4.7); 4.0380 (0.6); 4.0202 (0.6); 3.6210 (1.9); 3.6051 (5.0); 3.5904 (5.2); 3.5745 (2.1); 3.3267 (147.3); 2.9294 (6.1); 2.9131 (12.8); 2.8966 (5.6); 2.8241 (0.8); 2.8071 (2.2); 2.7900 (3.0); 2.7729 (2.2); 2.7558 (0.9); 2.6802 (0.4); 2.6757 (1.0); 2.6711 (1.3); 2.6665 (1.0); 2.6620 (0.5); 2.5246 (3.9); 2.5199 (6.0); 2.5113 (81.2); 2.5068 (169.4); 2.5022 (223.4); 2.4976 (156.6); 2.4930 (72.5); 2.3382 (0.5); 2.3336 (1.0); 2.3290 (1.4); 2.3244 (1.0); 2.3200 (0.5); 2.0740 (2.1); 2.0112 (0.4); 1.9888 (2.6); 1.2342 (0.4); 1.1931 (0.9); 1.1703 (15.3); 1.1532 (16.0); 1.1439 (15.7); 1.1268 (14.7); 1.0988 (0.4); 1.0696 (0.5); 0.8886 (0.5); 0.8718 (0.4); 0.1459 (1.3); 0.0080 (11.0); −0.0001 (324.4); −0.0086 (10.4); −0.0189 (0.5); −0.1496 (1.3) I-142 [00266]
I-142: 1H-NMR{400.2 MHz, d6-DMSO): δ = 8.3714 (4.6); 8.0599 (3.5); 8.0392 (4.3); 7.8287 (4.0); 7.8078 (3.5); 7.7604 (3.6); 7.7381 (4.8); 7.6030 (3.8); 7.5810 (3.0); 7.4088 (2.2); 7.3869 (2.6); 7.2784 (0.8); 7.2651 (1.6); 7.2513 (0.8); 7.0699 (1.4); 7.0633 (1.5); 7.0482 (1.3); 7.0414 (1.4); 6.8896 (3.1); 6.8829 (2.9); 4.2647 (1.6); 4.2214 (2.6); 4.1278 (2.7); 4.0845 (1.6); 3.7573 (16.0); 3.6230 (0.8); 3.6071 (2.1); 3.5924 (2.2); 3.5763 (0.9); 3.3266 (15.4); 2.9310 (2.3); 2.9147 (4.5); 2.8983 (2.1); 2.7431 (0.3); 2.7254 (0.8); 2.7086 (1.1); 2.6913 (0.9); 2.6748 (0.6); 2.5065 (39.6); 2.5023 (49.1); 2.4981 (36.1); 1.1382 (5.6); 1.1211 (5.8); 1.1090 (5.8); 1.0919 (5.4); 0.1460 (0.4); −0.0002 (71.1); −0.1496 (0.4)
NMR Data of Selected Examples
NMR Peak List Method
[0901] The NMR data of selected examples are stated in the form of NMR peak lists. For each signal peak, first the δ value in ppm and then the signal intensity in round brackets are listed. The δ value—signal intensity number pairs for different signal peaks are listed with separation from one another by semicolons.
[0902] The peak list for one example therefore has the form:
[0903] δ.sub.1 (intensity.sub.1); δ.sub.2 (intensity.sub.2); . . . ; δ.sub.i (intensity.sub.i); . . . ; δ.sub.n (intensity.sub.n)
[0904] The intensity of sharp signals correlates with the height of the signals in a printed example of an NMR spectrum in cm and shows the true ratios of the signal intensities. In the case of broad signals, several peaks or the middle of the signal and the relative intensity thereof may be shown in comparison to the most intense signal in the spectrum.
[0905] To calibrate the chemical shift of .sup.1H-NMR spectra, we use tetramethylsilane and/or the chemical shift of the solvent, particularly in the case of spectra measured in DMSO. Therefore, the tetramethylsilane peak may but need not occur in NMR peak lists.
[0906] The lists of the NMR peaks are similar to the conventional NMR printouts and thus usually contain all peaks listed in a conventional NMR interpretation.
[0907] In addition, like conventional NMR printouts, they may show solvent signals, signals of stereoisomers of the target compounds which are likewise provided by the invention, and/or peaks of impurities.
[0908] In the reporting of compound signals within the delta range of solvents and/or water, our lists of NMR peaks show the standard solvent peaks, for example peaks of DMSO in d.sub.6-DMSO and the peak of water, which usually have a high intensity on average.
[0909] The peaks of stereoisomers of the target compounds and/or peaks of impurities usually have a lower intensity on average than the peaks of the target compounds (for example with a purity of >90%).
[0910] Such stereoisomers and/or impurities may be typical of the particular preparation process. Their peaks can thus help in this case to identify reproduction of our preparation process with reference to “by-product fingerprints”.
[0911] An expert calculating the peaks of the target compounds by known methods (MestreC, ACD simulation, but also with empirically evaluated expected values) can, if required, isolate the peaks of the target compounds, optionally using additional intensity filters. This isolation would be similar to the peak picking in question in conventional .sup.1H NMR interpretation.
[0912] Further details of NMR peak lists can be found in the Research Disclosure Database Number 564025.
Use Examples
[0913] Boophilus microplus—Injection Test
Solvent: Dimethyl Sulfoxide
[0914] To produce a suitable active compound formulation, 10 mg of active compound are mixed with 0.5 ml of solvent and the concentrate is diluted to the desired concentration with solvent.
[0915] 1 μl of the active compound solution is injected into the abdomen of 5 engorged adult female cattle ticks (Boophilus microplus). The animals are transferred into dishes and kept in a climate-controlled room.
[0916] Efficacy is assessed after 7 days by laying of fertile eggs. Eggs which are not visibly fertile are stored in a climate-controlled cabinet until the larvae hatch after about 42 days. An efficacy of 100% means that none of the ticks has laid any fertile eggs; 0% means that all the eggs are fertile.
[0917] In this test, for example, the following compounds from the preparation examples showed an efficacy of 100% at an application rate of 20 μg/animal: I-003, I-007.
[0918] In this test, for example, the following compounds from the preparation examples showed an efficacy of 90% at an application rate of 20 μg/animal: I-005.
Ctenocephalides felis—In Vitro Contact Tests with Adult Cat Fleas
[0919] For the coating of the test tubes, 9 mg of active compound are first dissolved in 1 ml of acetone p.a. and then diluted to the desired concentration with acetone p.a. 250 μl of the solution are distributed homogeneously on the inner walls and the base of a 25 ml glass tube by turning and rocking on an orbital shaker (rocking rotation at 30 rpm for 2 h). With 900 ppm of active compound solution and internal surface area 44.7 cm.sup.2, given homogeneous distribution, an area-based dose of 5 μg/cm.sup.2 is achieved.
[0920] After the solvent has evaporated off, the tubes are populated with 5-10 adult cat fleas (Ctenocephalides felis), sealed with a perforated plastic lid and incubated in a horizontal position at room temperature and ambient humidity. After 48 h, efficacy is determined. To this end, the tubes are stood upright and the fleas are knocked to the base of the tube. Fleas which remain motionless at the base or move in an uncoordinated manner are considered to be dead or moribund.
[0921] A substance shows good efficacy against Ctenocephalides felis if at least 80% efficacy was achieved in this test at an application rate of 5 μg/cm.sup.2. 100% efficacy means that all the fleas were dead or moribund. 0% efficacy means that no fleas were harmed.
[0922] In this test, for example, the following compounds from the preparation examples showed an efficacy of 100% at an application rate of 5 μg/cm.sup.2 (=500 g of ai/ha): 1-009, 1-079, 1-090, 1-097, 1-117.
[0923] In this test, for example, the following compounds from the preparation examples showed an efficacy of 90% at an application rate of 5 μg/cm.sup.2 (=500 g of ai/ha): 1-083.
[0924] In this test, for example, the following compounds from the preparation examples showed an efficacy of 80% at an application rate of 5 μg/cm.sup.2 (=500 g of ai/ha): 1-018, 1-032.
Ctenocephalides felis—Oral Test
Solvent: Dimethyl Sulfoxide
[0925] To produce a suitable active compound formulation, 10 mg of active compound are mixed with 0.5 ml of dimethyl sulfoxide. Dilution with citrated cattle blood gives the desired concentration.
[0926] About 20 unfed adult cat fleas (Ctenocephalides felis) are placed into a chamber which is closed at the top and bottom with gauze. A metal cylinder whose bottom end is closed with parafilm is placed onto the chamber. The cylinder contains the blood/active compound formulation, which can be imbibed by the fleas through the parafilm membrane.
[0927] After 2 days, the kill in % is determined. 100% means that all of the fleas have been killed; 0% means that none of the fleas have been killed.
[0928] In this test, for example, the following compounds of the preparation examples showed an efficacy of 100% at an application rate of 100 ppm: 1-002, 1-003, 1-005, 1-008, 1-009, I-010, 1-013, 1-015.
[0929] In this test, for example, the following compounds of the preparation examples showed an efficacy of 95% at an application rate of 100 ppm: 1-006, 1-016, 1-017, 1-018.
[0930] In this test, for example, the following compounds of the preparation examples showed an efficacy of 90% at an application rate of 100 ppm: 1-007.
[0931] In this test, for example, the following compounds of the preparation examples showed an efficacy of 80% at an application rate of 100 ppm: 1-014.
Musca domestica Test
Solvent: Dimethyl Sulfoxide
[0932] To produce a suitable active compound formulation, 10 mg of active compound are mixed with 0.5 ml of dimethyl sulfoxide, and the concentrate is diluted with water to the desired concentration.
[0933] Vessels containing a sponge treated with sugar solution and the desired concentration of active compound formulation are populated with 10 adult houseflies (Musca domestica).
[0934] After 2 days, the kill in % is determined. 100% means that all of the flies have been killed; 0% means that none of the flies have been killed.
[0935] In this test, for example, the following compounds of the preparation examples showed an efficacy of 90% at an application rate of 100 ppm: 1-002.
[0936] In this test, for example, the following compounds of the preparation examples showed an efficacy of 80% at an application rate of 100 ppm: 1-005, 1-006, 1-008.
Diabrotica balteata—Spray Test
Solvent: 78 parts by weight of acetone [0937] 1.5 parts by weight of dimethylformamide
Emulsifier: alkylaryl polyglycol ether
[0938] To produce a suitable active compound formulation, 1 part by weight of active compound is dissolved using the stated parts by weight of solvent and made up with water containing an emulsifier concentration of 1000 ppm until the desired concentration is attained. To produce further test concentrations, the formulation is diluted with emulsifier-containing water.
[0939] Pre-swollen wheat grains (Triticum aestivum) are incubated in a multiwell plate filled with agar and a little water for one day (5 seed grains per cavity). The germinated wheat grains are sprayed with an active compound formulation of the desired concentration. Subsequently, each cavity is infected with 10-20 beetle larvae of Diabrotica balteata.
[0940] After 7 days, the efficacy in % is determined. 100% means that all wheat plants have grown as in the untreated, uninfected control; 0% means that no wheat plant has grown.
[0941] In this test, for example, the following compounds from the preparation examples showed an efficacy of 100% at an application rate of 500 g/ha (=160 μg/cavity): I-018, I-019, I-020, I-021, I-022, I-023, I-024, I-025, I-027, I-029, I-030, I-032, I-033, I-034, I-035, I-036, I-037, I-038, I-040, I-041, I-043, I-045, I-046, I-049, I-050, I-051, I-054, I-055, I-056, I-057, I-058, I-060, I-064, I-065, I-066, I-067, I-068.
[0942] In this test, for example, the following compounds from the preparation examples showed an efficacy of 80% at an application rate of 500 g/ha (=160 μg/cavity): 1-026, 1-044, 1-061, 1-062.
[0943] In this test, for example, the following compounds from the preparation examples show an efficacy of 100% at an application rate of 125 g/ha (=40 μg/cavity): I-018, I-019, I-021, I-022, I-023, I-024, I-025, I-027, I-029, I-032, I-033.
[0944] In this test, for example, the following compounds from the preparation examples show an efficacy of 80% at an application rate of 125 g/ha (=40 μg/cavity): 1-020.
[0945] In this test, for example, the following compounds from the preparation examples showed an efficacy of 100% at an application rate of 100 g/ha (=32 μg/cavity): I-034, I-041, I-042, I-043, I-045, I-046, I-049, I-050, I-051, I-052, I-056, I-057, I-058, I-060, I-064, I-065, I-066, I-067, I-068, I-070, I-071, I-072, I-073, I-075, I-079, I-080, I-082, I-083, I-084, I-086, I-087, I-088, I-090, I-091, I-093, I-094, I-095, I-096, I-097, I-098, I-100, I-102, I-103, I-104, I-105, I-106, I-107, I-108, I-109, I-110, I-111, I-112, I-113, I-114, I-116, I-117, I-118, I-119, I-120, I-122, I-123, I-124, I-125, I-126, I-127.
[0946] In this test, for example, the following compounds from the preparation examples showed an efficacy of 80% at an application rate of 100 g/ha (=32.sub.kg/cavity): I-035, I-036, I-037, I-038, I-039, I-040, I-044, I-055, I-061, I-085, I-099.
Meloidogyne incognita Test
Solvent: 125.0 parts by weight of acetone
[0947] To produce a suitable active compound formulation, 1 part by weight of active compound is mixed with the stated amount of solvent and the concentrate is diluted to the desired concentration with water.
[0948] Vessels are filled with sand, active compound solution, an egg/larvae suspension of the southern root-knot nematode (Meloidogyne incognita) and lettuce seeds. The lettuce seeds germinate and the plants develop. The galls develop on the roots.
[0949] After 14 days, the nematicidal efficacy in % is determined by the formation of galls. 100% means that no galls were found; 0% means that the number of galls on the treated plants corresponds to the untreated control.
[0950] In this test, for example, the following compounds from the preparation examples showed an efficacy of 100% at an application rate of 20 ppm: I-020, I-052, I-111.
[0951] In this test, for example, the following compounds from the preparation examples showed an efficacy of 90% at an application rate of 20 ppm: 1-017, 1-047, 1-048, I-051, 1-056, 1-104, 1-105, 1-107, 1-108, 1-109.
Myzus persicae—Oral Test
Solvent: 100 parts by weight of acetone
[0952] To produce a suitable active compound formulation, 1 part by weight of active compound is dissolved using the specified parts by weight of solvent and made up with water until the desired concentration is attained.
[0953] 50 μl of the active compound formulation are transferred into microtitre plates and made up to a final volume of 200 μl with 150 μl of IPL41 insect medium (33%+15% sugar). Subsequently, the plates are sealed with parafilm, which a mixed population of green peach aphids (Myzus persicae) within a second microtitre plate is able to puncture and imbibe the solution through.
[0954] After 5 days, the efficacy in % is determined. 100% means that all the aphids have been killed; 0% means that no aphids have been killed.
[0955] In this test, for example, the following compounds from the preparation examples showed an efficacy of 90% at an application rate of 4 ppm: 1-018, 1-057.
Nezara viridula—Spray Test
Solvent: 78.0 parts by weight of acetone [0956] 1.5 parts by weight of dimethylformamide
Emulsifier: alkylaryl polyglycol ether
[0957] To produce a suitable active compound formulation, 1 part by weight of active compound is dissolved using the stated parts by weight of solvent and made up with water containing an emulsifier concentration of 1000 ppm until the desired concentration is attained. To produce further test concentrations, the formulation is diluted with emulsifier-containing water.
[0958] Barley plants (Hordeum vulgare) are sprayed with an active compound formulation of the desired concentration and are infected with larvae of the Southern green shield bug (Nezara viridula).
[0959] After 4 days, the efficacy in % is determined. 100% means that all of the shield bugs have been killed; 0% means that none of the shield bugs have been killed.
[0960] In this test, for example, the following compounds from the preparation examples showed an efficacy of 100% at an application rate of 500 g/ha: 1-018.
Phaedon cochleariae—Spray Test
Solvent: 78.0 parts by weight of acetone [0961] 1.5 parts by weight of dimethylformamide
Emulsifier: alkylaryl polyglycol ether
[0962] To produce a suitable active compound formulation, 1 part by weight of active compound is dissolved using the stated parts by weight of solvent and made up with water containing an emulsifier concentration of 1000 ppm until the desired concentration is attained. To produce further test concentrations, the formulation is diluted with emulsifier-containing water.
[0963] Discs of Chinese cabbage leaves (Brassica pekinensis) are sprayed with an active compound formulation of the desired concentration and, after drying, populated with larvae of the mustard beetle (Phaedon cochleariae).
[0964] After 7 days, the efficacy in % is determined. 100% means that all the beetle larvae have been killed; 0% means that no beetle larvae have been killed.
[0965] In this test, for example, the following compounds from the preparation examples showed an efficacy of 100% at an application rate of 500 g/ha: I-001, 1-002, 1-003, 1-004, 1-005, 1-006, 1-007, 1-008.
[0966] In this test, for example, the following compounds from the preparation examples showed an efficacy of 100% at an application rate of 100 g/ha: 1-003, 1-004, 1-005, 1-006, 1-007, 1-008, 1-009, I-010, 1-012, I013, 1-014, 1-016, 1-017.
[0967] In this test, for example, the following compounds from the preparation examples showed an efficacy of 83% at an application rate of 100 g/ha: 1-002, 1-015.
Spodoptera frugiperda—Spray Test
Solvent: 78.0 parts by weight of acetone [0968] 1.5 parts by weight of dimethylformamide
Emulsifier: alkylaryl polyglycol ether
[0969] To produce a suitable active compound formulation, 1 part by weight of active compound is dissolved using the stated parts by weight of solvent and made up with water containing an emulsifier concentration of 1000 ppm until the desired concentration is attained. To produce further test concentrations, the formulation is diluted with emulsifier-containing water.
[0970] Leaf discs of maize (Zea mays) are sprayed with an active compound formulation of the desired concentration and, after drying, populated with caterpillars of the fall armyworm (Spodoptera frugiperda).
[0971] After 7 days, the efficacy in % is determined. 100% means that all the caterpillars have been killed; 0% means that no caterpillar has been killed.
[0972] In this test, for example, the following compounds from the preparation examples showed an efficacy of 100% at an application rate of 500 g/ha: I-001, I-002, I-003, I-005, I-006, I-007, I-008, I-045.
[0973] In this test, for example, the following compounds from the preparation examples showed an efficacy of 83% at an application rate of 500 g/ha: 1-004.
[0974] In this test, for example, the following compounds from the preparation examples showed an efficacy of 100% at an application rate of 100 g/ha: I-001, I-002, I-003, I-005, I-006, I-008, I-009, I-010, I-011, I-012, I-013, I-014, I-015, I-016, I-017, I-018, I-019, I-020, I-021, I-022, I-023, I-024, I-025, I-027, I-029, I-030, I-031, I-032, I-033, I-034, I-035, I-036, I-038, I-039, I-040, I-041, I-042, I-043, I-044, I-045, I-046, I-049, I-050, I-051, I-052, I-053, I-054, I-055, I-056, I-057, I-058, I-059, I-060, I-061, I-063, I-064, I-065, I-066, I-067, I-068, I-069, I-070, I-071, I-072, I-073, I-074, I-075, I-076, I-077, I-078, I-079, I-080, I-081, I-082, I-083, I-084, I-085, I-086, I-087, I-088, I-089, I-090, I-092, I-093, I-094, I-095, I-096, I-098, I-099, I-100, I-102, I-103, I-104, I-105, I-106, I-107, I-108, I-109, I-110, I-111, I-112, I-113, I-114, I-115, I-116, I-117, I-118, I-119, I-120, I-121, I-122, I-123, I-124, I-125, I-126, I-127, I-128, I-129, I-130, I-131, I-132, I-133, I-134, I-135, I-136, I-137, I-138, I-139, I-140, I-141, I-142.
[0975] In this test, for example, the following compounds from the preparation examples showed an efficacy of 83% at an application rate of 100 g/ha: 1-028, 1-037, 1-091, 1-097, I-101.
Tetranychus urticae—Spray Test, OP-Resistant
Solvent: 78.0 parts by weight of acetone [0976] 1.5 parts by weight of dimethylformamide
Emulsifier: alkylaryl polyglycol ether
[0977] To produce a suitable active compound formulation, 1 part by weight of active compound is dissolved using the stated parts by weight of solvent and made up with water containing an emulsifier concentration of 1000 ppm until the desired concentration is attained. To produce further test concentrations, the formulation is diluted with emulsifier-containing water.
[0978] Discs of bean leaves (Phaseolus vulgaris) infested with all stages of the greenhouse red spider mite (Tetranychus urticae) are sprayed with an active compound formulation of the desired concentration.
[0979] After 6 days, the efficacy in % is determined. 100% means that all the spider mites have been killed; 0% means that no spider mites have been killed.
[0980] In this test, for example, the following compounds from the preparation examples showed an efficacy of 100% at an application rate of 100 g/ha: 1-006.
[0981] In this test, for example, the following compounds from the preparation examples showed an efficacy of 90% at an application rate of 100 g/ha: I-001, 1-060.