Substituted 5-hydroxy-2-heteroaryl-3-phenylpentanonitrile derivatives, processes for their preparation and their use as herbicides and/or plant growth regulators
20170166549 ยท 2017-06-15
Assignee
Inventors
- MARC MOSRIN (KOELN, DE)
- Harald Jakobi (Frankfurt, DE)
- Hansjoerg Dietrich (Liederbach am Taunus, DE)
- Elmar Gatzweiler (Bad Nauheim, DE)
- Christopher Hugh Rosinger (Hofheim, DE)
- Dirk Schmutzler (Hattersheim, DE)
Cpc classification
C07D307/56
CHEMISTRY; METALLURGY
A01N43/66
HUMAN NECESSITIES
C07D263/32
CHEMISTRY; METALLURGY
C07D239/26
CHEMISTRY; METALLURGY
C07D333/24
CHEMISTRY; METALLURGY
C07D277/32
CHEMISTRY; METALLURGY
C07D253/065
CHEMISTRY; METALLURGY
C07D263/34
CHEMISTRY; METALLURGY
A01N43/48
HUMAN NECESSITIES
C07D233/64
CHEMISTRY; METALLURGY
C07D231/12
CHEMISTRY; METALLURGY
C07D237/08
CHEMISTRY; METALLURGY
C07D307/54
CHEMISTRY; METALLURGY
C07D253/07
CHEMISTRY; METALLURGY
C07D241/12
CHEMISTRY; METALLURGY
A01N43/707
HUMAN NECESSITIES
C07D277/30
CHEMISTRY; METALLURGY
International classification
C07D307/54
CHEMISTRY; METALLURGY
C07D253/07
CHEMISTRY; METALLURGY
C07D237/08
CHEMISTRY; METALLURGY
C07D239/26
CHEMISTRY; METALLURGY
A01N43/66
HUMAN NECESSITIES
C07D231/12
CHEMISTRY; METALLURGY
C07D263/34
CHEMISTRY; METALLURGY
C07D333/24
CHEMISTRY; METALLURGY
C07D251/20
CHEMISTRY; METALLURGY
C07D253/065
CHEMISTRY; METALLURGY
C07D233/64
CHEMISTRY; METALLURGY
C07D277/32
CHEMISTRY; METALLURGY
A01N43/707
HUMAN NECESSITIES
C07D307/56
CHEMISTRY; METALLURGY
A01N43/48
HUMAN NECESSITIES
C07D241/12
CHEMISTRY; METALLURGY
C07D263/32
CHEMISTRY; METALLURGY
Abstract
Primarily, the present invention relates to compounds of the formula (I) defined below and to their use as herbicides, in particular for controlling broad-leaved weeds and/or weed grasses in crops of useful plants and/or as plant growth regulators for influencing the growth of crops of useful plants. The present invention also relates to herbicidal or plant growth-regulating compositions comprising one or more compounds of the formula (I). Moreover, the present invention relates to processes for preparing the compounds of the formula (I).
Claims
1. A compound of formula (I) and/or salt thereof, ##STR00014## wherein Q represents a mono- or bicyclic heteroaromatic radical with in total 1 to 9 carbon ring atoms, where the heteroatom or heteroatoms in the heteroaromatic ring are selected from the group consisting of N, O, S, P, B, Si, and Se, R.sup.1 represents hydrogen or a hydrolyzable radical, (R.sup.2).sub.n represent n substituents R.sup.2, where R.sup.2 (if n=1) or each of the substituents R.sup.2 (if n is greater than 1) independently of one another represents halogen, cyano, nitro, (C.sub.1-C.sub.8)alkyl, (C.sub.1-C.sub.8)alkoxy, (C.sub.1-C.sub.8)alkylthio, (C.sub.1-C.sub.8)alkylsulfinyl, (C.sub.1-C.sub.8)alkylsulfonyl, (C.sub.1-C.sub.6)haloalkyl, (C.sub.2-C.sub.6)haloalkenyl, (C.sub.1-C.sub.6)haloalkoxy, (C.sub.1-C.sub.6)haloalkylthio, (C.sub.1-C.sub.6)haloalkylsulfinyl, (C.sub.1-C.sub.6)haloalkylsulfonyl, (C.sub.2-C.sub.6)alkenyl, (C.sub.2-C.sub.6)alkynyl, tri-[(C.sub.1-C.sub.4)alkyl]silyl or tri-[(C.sub.1-C.sub.4)alkyl]silyl-(C.sub.1-C.sub.4)alkyl, or in each case two R.sup.2 directly adjacent on the heteroaromatic radical Q are together a group of the formula Z.sup.1-A*.sup.1-Z.sup.2, in which A* represents an alkylene group having 1 to 4 carbon atoms which is optionally substituted by one or more radicals selected from the group consisting of halogen, (C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4)haloalkyl, (C.sub.1-C.sub.4)alkoxy and (C.sub.1-C.sub.4)haloalkoxy, Z.sup.1 represents a direct bond, O or S and Z.sup.2 represents a direct bond, O or S, where the group Z.sup.1-A*-Z.sup.2 together with the atoms of the heteroaromatic radical Q bonded to this group Q form a 5- or 6-membered ring, and (R.sup.3).sub.m represents m substituents R.sup.3, where R.sup.3 (if m=1) or each of the substituents R.sup.3 (if m is greater than 1) independently of one another represents halogen, cyano, nitro, (C.sub.1-C.sub.8)alkyl, (C.sub.1-C.sub.8)alkoxy, (C.sub.1-C.sub.8)alkylthio, (C.sub.1-C.sub.8)alkylsulfinyl, (C.sub.1-C.sub.8)alkylsulfonyl, (C.sub.1-C.sub.6)haloalkyl, (C.sub.2-C.sub.6)haloalkenyl, (C.sub.1-C.sub.6)haloalkoxy, (C.sub.1-C.sub.6)haloalkylthio, (C.sub.1-C.sub.6)haloalkylsulfinyl, (C.sub.1-C.sub.6)haloalkylsulfonyl, (C.sub.2-C.sub.6)alkenyl, (C.sub.2-C.sub.6)alkynyl, tri-[(C.sub.1-C.sub.4)alkyl]silyl, tri-[(C.sub.1-C.sub.4)alkyl]silyl-(C.sub.1-C.sub.4)alkyl or NR*R**, where R* and R**, independently of one another and independently of any other radicals NR*R** present, are in each case selected from the group consisting of H, (C.sub.1-C.sub.8)alkyl, (C.sub.2-C.sub.8)alkenyl, (C.sub.2-C.sub.8)alkynyl, (C.sub.1-C.sub.4)alkoxy-(C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.6)alkanoyl, [(C.sub.1-C.sub.4)haloalkyl]carbonyl, [(C.sub.1-C.sub.4)alkoxy]carbonyl, [(C.sub.1-C.sub.4)haloalkoxy]carbonyl, (C.sub.3-C.sub.6)cycloalkyl, (C.sub.3-C.sub.6)cycloalkyl-(C.sub.1-C.sub.4)alkyl, (C.sub.3-C.sub.6)cycloalkenyl, (C.sub.3-C.sub.6)cycloalkenyl-(C.sub.1-C.sub.4)alkyl, phenyl and phenyl-(C.sub.1-C.sub.4)alkyl, where each of the specified radicals (C.sub.3-C.sub.6)cycloalkyl, (C.sub.3-C.sub.6)cycloalkyl-(C.sub.1-C.sub.4)alkyl, (C.sub.3-C.sub.6)cycloalkenyl, (C.sub.3-C.sub.6)cycloalkenyl-(C.sub.1-C.sub.4)alkyl, phenyl and phenyl-(C.sub.1-C.sub.4)alkyl is substituted in the cycle optionally by one or more identical or different radicals R.sup.bb, where R.sup.bb in each case represents halogen, (C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4)haloalkyl, (C.sub.1-C.sub.4)alkoxy or (C.sub.1-C.sub.4)haloalkoxy and, in the case of (C.sub.3-C.sub.6)cycloalkyl, (C.sub.3-C.sub.6)cycloalkyl-(C.sub.1-C.sub.4)alkyl, (C.sub.3-C.sub.6)cycloalkenyl, (C.sub.3-C.sub.6)cycloalkenyl-(C.sub.1-C.sub.4)alkyl, R.sup.bb may additionally represent oxo, or NR*R** represents a 3- to 8-membered heterocycle which, in addition to this nitrogen atom, optionally contains one or two further ring heteroatoms selected from the group consisting of N, O and S and which is unsubstituted or substituted by one or more radicals selected from the group consisting of (C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4)haloalkyl and oxo, or where in each case two groups R.sup.3 directly adjacent on the ring together represent a group of the formula Z.sup.3-A**-Z.sup.4, in which A** represents an alkylene group having 1 to 4 carbon atoms which is optionally substituted by one or more radicals selected from the group consisting of halogen, (C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4)haloalkyl, (C.sub.1-C.sub.4)alkoxy and (C.sub.1-C.sub.4)haloalkoxy, Z.sup.3 represents a direct bond, O or S and Z.sup.4 represents a direct bond, O or S, where the group Z.sup.3-A**-Z.sup.4 together with the carbon atoms, bonded to this group, of the phenyl ring form a 5- or 6-membered ring, n represents 0, or an integer in the range from 1 to 5, optionally 0, 1, 2 or 3, and m represents 0, 1, 2, 3, 4 or 5, optionally 0, 1, 2 or 3.
2. The compound of formula (I) and/or salt thereof according to claim 1, wherein Q represents a mono- or bicyclic heteroaromatic radical having in total 2 to 9 carbon ring atoms, where the heteroaromatic radical Q contains 1, 2, 3 or 4 heteroatoms in the heteroaromatic ring and the heteroatom or the heteroatoms are selected from the group consisting of N, O, and S.
3. The compound of formula (I) and/or salt thereof as claimed in claim 1, wherein Q represents a mono- or bicyclic heteroaromatic radical selected from the group consisting of pyrimidinyl, pyridinyl, pyridazinyl, pyrazinyl, thienyl, furyl, oxazolyl, thiazolyl, imidazolyl, pyrazolyl, triazinyl, quinolyl, isoquinolyl, cinnolinyl-, quinazolinyl, quinoxalinyl, pteridinyl, indolyl and phthalazinyl.
4. The compound of formula (I) and/or salt thereof as claimed in claim 1, wherein the compound of the formula (I) corresponds to the formula (I-1), (I-2) or (I-3) defined below ##STR00015##
5. The compound of formula (I) and/or salt thereof as claimed in claim 1, wherein R.sup.1 represents hydrogen or a hydrolyzable radical having in total up to 30 carbon atoms, with preference a hydrolyzable radical having in total 1 to 24 carbon atoms, optionally having in total 1 to 20 carbon atoms.
6. The compound of formula (I) and/or salt thereof as claimed in claim 1, wherein R.sup.1 represents hydrogen or a hydrolyzable radical having in total 1 to 24 carbon atoms, where R.sup.1 represents an optionally substituted hydrocarbon radical or an optionally substituted heterocyclyl radical, or R.sup.b represents a radical of the formula SiR.sup.aR.sup.bR.sup.c, or NR.sup.aR.sup.b, where each of the radicals R.sup.a and R.sup.b independently of the other represents hydrogen or an optionally substituted hydrocarbon radical and R.sup.c independently represents an optionally substituted hydrocarbon radical, or NR.sup.aR.sup.b represents a 3- to 9-membered heterocycle which, in addition to this nitrogen atom, may contain one or two further ring heteroatoms from the group consisting of N, O and S and which is substituted or unsubstituted, or represents a radical of the formula C(O)R.sup.e or P(O)(R.sup.f).sub.2, where R.sup.e and both radicals R.sup.f in each case independently of one another are selected from the group consisting of hydrogen, OH, unsubstituted or substituted (C.sub.1-C.sub.8)alkyl, unsubstituted or substituted (C.sub.1-C.sub.4)haloalkyl, unsubstituted or substituted (C.sub.2-C.sub.8)alkenyl, unsubstituted or substituted (C.sub.2-C.sub.8)alkynyl, unsubstituted or substituted (C.sub.1-C.sub.6)alkoxy, unsubstituted or substituted (C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.8)alkyl, unsubstituted or substituted (C.sub.1-C.sub.4)haloalkoxy, unsubstituted or substituted (C.sub.1-C.sub.4)haloalkoxy-(C.sub.1-C.sub.8)alkyl, unsubstituted or substituted (C.sub.3-C.sub.8)alkenyloxy, unsubstituted or substituted (C.sub.3-C.sub.8)alkenyloxy-(C.sub.1-C.sub.8)alkyl, unsubstituted or substituted (C.sub.3-C.sub.8)alkynyloxy, unsubstituted or substituted (C.sub.3-C.sub.8)alkynyloxy-(C.sub.1-C.sub.8)alkyl, unsubstituted or substituted NR*R**, where R* and R** are as defined above, unsubstituted or substituted tri-[(C.sub.1-C.sub.4)alkyl]silyl, unsubstituted or substituted tri-[(C.sub.1-C.sub.4)alkyl]silyl-(C.sub.1-C.sub.8)alkyl, unsubstituted or substituted (C.sub.3-C.sub.6)cycloalkyl, unsubstituted or substituted (C.sub.3-C.sub.6)cycloalkyl-(C.sub.1-C.sub.8)alkyl, unsubstituted or substituted (C.sub.5-C.sub.6)cycloalkenyl, unsubstituted or substituted (C.sub.5-C.sub.6)cycloalkenyl-(C.sub.1-C.sub.8)alkyl, unsubstituted or substituted (C.sub.5-C.sub.6)cycloalkynyl, unsubstituted or substituted (C.sub.5-C.sub.6)cycloalkynyl-(C.sub.1-C.sub.8)alkyl, unsubstituted or substituted phenyl, unsubstituted or substituted phenyl-(C.sub.1-C.sub.8)alkyl, unsubstituted or substituted phenoxy, unsubstituted or substituted phenoxy-(C.sub.1-C.sub.8)alkyl, unsubstituted or substituted phenylamino, unsubstituted or substituted phenylamino(C.sub.1-C.sub.8)alkyl, unsubstituted or substituted Het, unsubstituted or substituted Het-(C.sub.1-C.sub.6)alkyl and unsubstituted or substituted Het-O(C.sub.1-C.sub.6)alkyl, where Het in each case represents a saturated, partially unsaturated or heteroaromatic monocyclic heterocyclyl radical having 3 to 9 ring atoms or a 9- or 10-membered bicyclic heterocycle in each case containing 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S, where each of the specified substituted radicals is substituted in the acyclic moiety by one or more identical or different radicals R.sup.A and/or where each of the specified substituted radicals is substituted in the cyclic moiety by one or more identical or different radicals R.sup.B, where R.sup.A represents halogen, cyano, hydroxy or (C.sub.1-C.sub.6)alkoxy, and R.sup.B independently of any further radicals R.sup.B present is selected from the group consisting of halogen, cyano, hydroxy, oxo, nitro, (C.sub.1-C.sub.8)alkyl, (C.sub.1-C.sub.6)haloalkyl, cyano-(C.sub.1-C.sub.6)alkyl, hydroxy-(C.sub.1-C.sub.6)alkyl, nitro-(C.sub.1-C.sub.6)alkyl, (C.sub.2-C.sub.8)alkenyl, (C.sub.2-C.sub.8)haloalkenyl, (C.sub.2-C.sub.8)alkynyl, (C.sub.2-C.sub.8)haloalkynyl, (C.sub.1-C.sub.8)alkoxy, (C.sub.2-C.sub.8)alkenyloxy, (C.sub.2-C.sub.8)alkynyloxy, (C.sub.1-C.sub.8)haloalkoxy, (C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.6)haloalkoxy-(C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.6)haloalkoxy-(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.8)alkylthio, (C.sub.2-C.sub.6)alkenylthio, (C.sub.2-C.sub.6)alkynylthio, (C.sub.1-C.sub.8)alkylsulfinyl, (C.sub.1-C.sub.6)haloalkylsulfinyl, (C.sub.1-C.sub.8)alkylsulfonyl, (C.sub.1-C.sub.6)haloalkylsulfonyl, R.sup.aaC(O), R.sup.aaC(O)(C.sub.1-C.sub.6)alkyl, NR*R**, tri-[(C.sub.1-C.sub.4)alkyl]silyl, tri-[(C.sub.1-C.sub.4)alkyl]silyl-(C.sub.1-C.sub.6)alkyl, (C.sub.3-C.sub.8)cycloalkyl, (C.sub.3-C.sub.8)cycloalkoxy, (C.sub.3-C.sub.8)cycloalkyl-(C.sub.1-C.sub.8)alkyl, (C.sub.3-C.sub.8)cycloalkyl-(C.sub.1-C.sub.8)alkoxy, phenyl, phenyl-(C.sub.1-C.sub.8)alkyl, phenoxy, phenoxy-(C.sub.1-C.sub.8)alkyl, phenylamino, phenylamino-(C.sub.1-C.sub.8)alkyl or a 5- or 6-membered monocyclic or 9- or 10-membered bicyclic heterocycle containing 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S, where each of these specified radicals can be substituted in the cyclic moiety by one or more identical or different R.sup.bb, where R.sup.aa in each case independently of one another represent hydrogen, OH, (C.sub.1-C.sub.8)alkyl, (C.sub.1-C.sub.6)haloalkyl, (C.sub.2-C.sub.8)alkenyl, (C.sub.2-C.sub.8)alkynyl, (C.sub.1-C.sub.8)alkoxy, (C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkyloxy, (C.sub.1-C.sub.6)haloalkoxy, (C.sub.1-C.sub.6)haloalkoxy-(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)haloalkoxy-(C.sub.1-C.sub.6)alkoxy, (C.sub.3-C.sub.8)alkenyloxy, (C.sub.3-C.sub.8)alkenyloxy-(C.sub.1-C.sub.6)alkyl, (C.sub.3-C.sub.8)alkenyloxy-(C.sub.1-C.sub.6)alkoxy, (C.sub.3-C.sub.8)alkynyloxy, (C.sub.3-C.sub.8)alkynyloxy-(C.sub.1-C.sub.6)alkyl, (C.sub.3-C.sub.8)alkynyloxy-(C.sub.1-C.sub.6)alkoxy, NR*R**, tri-[(C.sub.1-C.sub.4)alkyl]silyl, tri-[(C.sub.1-C.sub.4)alkyl]silyl-(C.sub.1-C.sub.6)alkyl, tri-[(C.sub.1-C.sub.4)alkyl]silyl-(C.sub.1-C.sub.6)alkoxy, (C.sub.3-C.sub.8)cycloalkyl, (C.sub.3-C.sub.8)cycloalkoxy, (C.sub.3-C.sub.8)cycloalkyl-(C.sub.1-C.sub.8)alkyl, (C.sub.3-C.sub.8)cycloalkyl-(C.sub.1-C.sub.8)alkoxy, (C.sub.5-C.sub.8)cycloalkenyl, (C.sub.5-C.sub.8)cycloalkenyl-(C.sub.1-C.sub.6)alkyl, (C.sub.5-C.sub.8)cycloalkenyloxy, (C.sub.5-C.sub.8)cycloalkynyl, (C.sub.5-C.sub.8)cycloalkynyl-(C.sub.1-C.sub.6)alkyl, (C.sub.5-C.sub.8)cycloalkynyl-(C.sub.1-C.sub.6)alkoxy, phenyl, phenyl-(C.sub.1-C.sub.8)alkyl, phenyl-(C.sub.1-C.sub.8)alkoxy, phenoxy, phenoxy-(C.sub.1-C.sub.8)alkyl, phenoxy-(C.sub.1-C.sub.8)alkoxy, phenylamino, phenylamino-(C.sub.1-C.sub.8)alkyl, phenylamino-(C.sub.1-C.sub.8)alkoxy or a 5- or 6-membered monocyclic or 9- or 10-membered bicyclic heterocycle containing 1, 2, 3 or 4 heteroatoms and optionally bonded via an alkylene group or an alkoxy group is selected from the group consisting of O, N and S, where each of the radicals R.sup.aa encompassing a cycle is optionally substituted in the cyclic moiety by one or more identical or different radicals R.sup.bb, and where R*, R**, NR*R** and R.sup.bb have the meaning given above.
7. The compound of formula (I) and/or salt thereof as claimed in claim 1, wherein R.sup.1 represents hydrogen, unsubstituted (C.sub.1-C.sub.18)alkyl, unsubstituted (C.sub.2-C.sub.18)alkenyl, unsubstituted (C.sub.2-C.sub.18)alkynyl, substituted (C.sub.1-C.sub.18)alkyl, substituted (C.sub.2-C.sub.18)alkenyl or substituted (C.sub.2-C.sub.18)alkynyl, where in the case of substituted (C.sub.1-C.sub.18)alkyl, substituted (C.sub.2-C.sub.18)alkenyl and substituted (C.sub.2-C.sub.18)alkynyl the substituent(s) is/are each independently of one another selected from groups (a)-(e) below: (a) halogen, cyano, thio, nitro, hydroxy, carboxy, (C.sub.1-C.sub.8)alkoxy, (C.sub.2-C.sub.8)alkenyloxy, (C.sub.2-C.sub.8)alkynyloxy, (C.sub.1-C.sub.8)haloalkoxy, (C.sub.1-C.sub.4)alkoxy-(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.8)alkylthio, (C.sub.2-C.sub.8)alkenylthio, (C.sub.2-C.sub.8)alkyinylthio, (C.sub.1-C.sub.8)haloalkylthio, (C.sub.2-C.sub.8)haloalkenylthio, (C.sub.2-C.sub.8)haloalkinylthio, (C.sub.1-C.sub.8)alkylsulfinyl, (C.sub.2-C.sub.8)alkenyl sulfinyl, (C.sub.2-C.sub.8)alkynylsulfinyl, (C.sub.1-C.sub.8)haloalkylsulfinyl, (C.sub.2-C.sub.8)haloalkenylsulfinyl, (C.sub.2-C.sub.8)haloalkinylsulfinyl, (C.sub.1-C.sub.8)alkylsulfonyl, (C.sub.2-C.sub.8)alkenyl sulfonyl, (C.sub.2-C.sub.8)alkynylsulfonyl, (C.sub.1-C.sub.8)haloalkylsulfonyl, (C.sub.2-C.sub.8)haloalkenyl sulfonyl, (C.sub.2-C.sub.8)haloalkynylsulfonyl, NR*R**, where R*, R** and NR*R** in each case have the meaning given above, (b) (C.sub.3-C.sub.8)cycloalkyl, (C.sub.5-C.sub.8)cycloalkenyl, (C.sub.5-C.sub.8)cycloalkinyl, (C.sub.3-C.sub.8)cycloalkyl-(C.sub.1-C.sub.6)alkoxy, (C.sub.3-C.sub.8)cycloalkyl-(C.sub.1-C.sub.6)alkyl-S(O).sub.p, (C.sub.5-C.sub.8)cycloalkenyl-(C.sub.1-C.sub.6)alkoxy, (C.sub.5-C.sub.8)cycloalkenyl-(C.sub.1-C.sub.6)alkyl-S(O).sub.p, (C.sub.5-C.sub.8)cycloalkynyl-(C.sub.1-C.sub.6)alkoxy, (C.sub.5-C.sub.8)cycloalkynyl-(C.sub.1-C.sub.6)alkyl-S(O).sub.p, (C.sub.3-C.sub.8)cycloalkoxy, (C.sub.3-C.sub.8)cycloalkyl-S(O).sub.p, (C.sub.5-C.sub.8)cycloalkenyloxy, (C.sub.5-C.sub.8)cycloalkenyl-S(O).sub.p, (C.sub.5-C.sub.8)cycloalkynyloxy, (C.sub.5-C.sub.8)cycloalkynyl-S(O).sub.p, (C.sub.3-C.sub.8)cycloalkoxy-(C.sub.1-C.sub.6)alkoxy, (C.sub.3-C.sub.8)cycloalkoxy-(C.sub.1-C.sub.6)alkyl-S(O).sub.p, phenyl, phenyl(C.sub.1-C.sub.6)alkoxy, phenoxy, phenyl-S(O).sub.p, phenyl-(C.sub.1-C.sub.6)alkyl-S(O).sub.p, phenoxy-(C.sub.1-C.sub.6)alkoxy, phenoxy-(C.sub.1-C.sub.6)alkyl-S(O).sub.p, a radical Het.sup.1, Het.sup.1-S(O).sub.p, Het.sup.1-(C.sub.1-C.sub.6)alkoxy, Het.sup.1-O, Het.sup.1-O(C.sub.1-C.sub.6)alkoxy, where the radical Het.sup.1 has the meaning given above, and where each of the last-mentioned radicals of the group (b) in the acyclic moiety is unsubstituted or substituted by one or more identical or different radicals selected from the group consisting of halogen, cyano, hydroxy and (C.sub.1-C.sub.6)alkoxy, and/or in the cyclic moiety is unsubstituted or substituted by one or more identical or different radicals R.sup.B, where R.sup.B has the meaning given above, and the index p is in each case 0, 1 or 2, (c) C(O)R.sup.C, C(O)OR.sup.C, OC(O)R.sup.C, OC(O)OR.sup.C, C(O)SR.sup.C, C(S)SR.sup.C, C(O)NR*R**, C(O)ONR*R**, OC(O)NR*R**, N(R*)C(O)R.sup.C, N(R*)C(O)NR*R**, N(R*)C(O)OR.sup.C, P(O)(R.sup.C)(R.sup.D), P(O)(OR.sup.C)(R.sup.D), P(O)(OR.sup.C)(OR.sup.D) or OP(O)(OR.sup.C)(OR.sup.D), where R*, R** and NR*R** in each case have the meaning given above and R.sup.C and R.sup.D are as defined below, (d) SiR.sub.3, OSiR.sub.3, (R).sub.3Si(C.sub.1-C.sub.6)alkoxy, COONR.sub.2, ONCR.sub.2, NCR.sub.2, ONR.sub.2, CH(OR).sub.2 and O(CH.sub.2).sub.qCH(OR).sub.2, in which each of the radicals R is independently selected from the group consisting of H, (C.sub.1-C.sub.4)alkyl or phenyl which is unsubstituted or substituted by one or more radicals from the group consisting of halogen, (C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)haloalkyl, (C.sub.1-C.sub.4)haloalkoxy and nitro or substituted at two adjacent positions by a (C.sub.2-C.sub.6)alkylene bridge, and the index q represents an integer from 0 to 6, and (e) ROCHR CH(OR)(C.sub.1-C.sub.6)alkoxy, in which each of the radicals R independently of the others represents H or (C.sub.1-C.sub.4)-alkyl or together the radicals represent a (C.sub.1-C.sub.6)-alkylene group and R represents H or (C.sub.1-C.sub.4)-alkyl, or R.sup.1 (C.sub.3-C.sub.9)cycloalkyl, (C.sub.5-C.sub.9)cycloalkenyl, (C.sub.5-C.sub.9)cycloalkynyl or phenyl, where each of these radicals is unsubstituted or substituted by one or more radicals from the group consisting of the radicals of subgroups (a)-(e) below: (a) halogen, cyano, thio, nitro, hydroxy, carboxy, (C.sub.1-C.sub.8)alkyl, (C.sub.1-C.sub.8)haloalkyl, (C.sub.1-C.sub.4)alkoxy-(C.sub.1-C.sub.4)alkyl, (C.sub.2-C.sub.8)alkenyl, (C.sub.2-C.sub.8)haloalkenyl, (C.sub.2-C.sub.8)alkynyl, (C.sub.2-C.sub.8)haloalkynyl, (C.sub.1-C.sub.8)alkoxy, (C.sub.2-C.sub.8)alkenyloxy, (C.sub.2-C.sub.8)alkynyloxy, (C.sub.1-C.sub.8)haloalkoxy, (C.sub.1-C.sub.4)alkoxy-(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.8)alkylthio, (C.sub.2-C.sub.8)alkenylthio, (C.sub.2-C.sub.8)alkynylthio and NR*R**, where R*, R**, NR*R**, and R.sup.bb in each case have the meaning given above, (b) radicals of the formulae C(O)R.sup.C, C(O)OR.sup.C, OC(O)R.sup.C, OC(O)OR.sup.C, C(O)SR.sup.C, C(S)SR.sup.C, C(O)NR*R**, C(O)ONR*R**, OC(O)NR*R**, N(R*)C(O)R.sup.C, N(R*)C(O)NR*R**, N(R*)C(O)OR.sup.C, P(O)(R.sup.C)(R.sup.D), P(O)(OR.sup.C)(R.sup.D), P(O)(OR.sup.C)(OR.sup.D) or OP(O)(OR.sup.C)(OR.sup.D), where R*, R**, NR*R** and R.sup.bb in each case have the meaning given above and R.sup.C and R.sup.D have the meaning defined below, (c) radicals of the formulae SiR.sub.3, OSiR.sub.3, (R).sub.3Si(C.sub.1-C.sub.6)alkoxy, COONR.sub.2, ONCR.sub.2, NCR.sub.2, ONR.sub.2, CH(OR).sub.2 and O(CH.sub.2).sub.qCH(OR).sub.2, in which each of the radicals R.sup.1 independently of the others represents H, (C.sub.1-C.sub.4)-alkyl or phenyl which is unsubstituted or substituted by one or more radicals from the group consisting of halogen, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.1-C.sub.4)-haloalkoxy and nitro or is substituted at two adjacent positions by a (C.sub.2-C.sub.6)-alkylene bridge, and q represents an integer from 0 to 6, and (d) radicals of the formula ROCHRCH(OR)(C.sub.1-C.sub.6)alkoxy, in which each of the radicals R independently of the others represents H or (C.sub.1-C.sub.4)-alkyl or together the radicals represent a (C.sub.1-C.sub.6)-alkylene group and R represents H or (C.sub.1-C.sub.4)-alkyl, and (e) a radical of the formula Het.sup.1 which is unsubstituted or substituted by one or more identical or different radicals R.sup.B, where R.sup.B has the meaning given above, or R.sup.1 represents a polycyclic radical based on (C.sub.3-C.sub.9)cycloalkyl, (C.sub.5-C.sub.9)cycloalkenyl, (C.sub.5-C.sub.9)cycloalkynyl or phenyl, where the base ring is fused with a carbocyclic or heterocyclic ring, and where the base ring or the polycyclic system is unsubstituted or substituted by one or more identical or different radicals R.sup.B, where R.sup.B has the meaning given above, or R.sup.1 represents a heterocyclic radical Het.sup.1 which is unsubstituted in the ring or in the polycyclic system or substituted by one or more identical or different radicals R.sup.B, where R.sup.B has the meaning given above, where Het.sup.1 in each case independently of the others is a saturated, partially unsaturated or heteroaromatic monocyclic heterocyclyl radical having 3 to 9 ring atoms, optionally having 5 or 6 ring atoms, or a 9- or 10-membered bicyclic heterocycle containing 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S, optionally a 5- or 6-membered heterocycle having 1 to 3 ring heteroatoms from the group consisting of N, O and S which is optionally also fused to a carbocyclic or heterocyclic ring, optionally a carbocyclic ring having 3 to 6 carbon atoms or a heterocyclic ring having 5 or 6 ring atoms and 1 to 3 ring heteroatoms from the group consisting of N, O and S, optionally benzo-fused, R.sup.A has the meaning given above, R.sup.B has the meaning given above, and where R.sup.B optionally represents a radical selected from the group consisting of halogen, cyano, hydroxy, oxo, nitro, (C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.4)haloalkyl, cyano-(C.sub.1-C.sub.4)alkyl, hydroxy-(C.sub.1-C.sub.4)alkyl, nitro-(C.sub.1-C.sub.4)alkyl, (C.sub.2-C.sub.6)alkenyl, (C.sub.2-C.sub.6)haloalkenyl, (C.sub.2-C.sub.6)alkynyl, (C.sub.2-C.sub.6)haloalkynyl, (C.sub.1-C.sub.6)alkoxy, (C.sub.2-C.sub.6)alkenyloxy, (C.sub.2-C.sub.6)alkynyloxy, (C.sub.1-C.sub.6)haloalkoxy, (C.sub.1-C.sub.4)alkoxy-(C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4)alkoxy-(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)haloalkoxy-(C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4)haloalkoxy-(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.6)alkylthio, (C.sub.2-C.sub.6)alkenylthio, (C.sub.2-C.sub.6)alkynylthio, (C.sub.1-C.sub.6)alkylsulfinyl, (C.sub.1-C.sub.6)haloalkylsulfinyl, (C.sub.1-C.sub.6)alkylsulfonyl, (C.sub.1-C.sub.6)haloalkylsulfonyl, a radical of the formula .sup.aaC(O) or R.sup.aaC(O)(C.sub.1-C.sub.6)alkyl, where R.sup.aa has the meaning given above, NR*R**, where R*, R**, NR*R**, and R.sup.bb in each case have the meaning given above, tri-[(C.sub.1-C.sub.4)alkyl]silyl, tri-[(C.sub.1-C.sub.4)alkyl]silyl-(C.sub.1-C.sub.6)alkyl, (C.sub.3-C.sub.6)cycloalkyl, (C.sub.3-C.sub.6)cycloalkoxy, (C.sub.3-C.sub.6)cycloalkyl-(C.sub.1-C.sub.4)alkyl, (C.sub.3-C.sub.6)cycloalkyl-(C.sub.1-C.sub.8)alkoxy, phenyl, phenyl-(C.sub.1-C.sub.6)alkyl, phenoxy, phenoxy-(C.sub.1-C.sub.6)alkyl, phenylamino, phenylamino-(C.sub.1-C.sub.6)alkyl, or a 5- or 6-membered monocyclic or 9- or 10-membered bicyclic heterocycle containing 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S, where each of the radicals R.sup.B in the cyclic moiety is optionally substituted by one or more identical or different radicals R.sup.bb, where R.sup.B and R.sup.bb in each case have the meaning given above, R.sup.C and R.sup.D each independently of one another (and also independently of radicals R.sup.C, R.sup.D in other groups) represent a radical selected from the group consisting of: (i) hydrogen, unsubstituted (C.sub.1-C.sub.8)alkyl, unsubstituted (C.sub.2-C.sub.8)alkenyl, unsubstituted (C.sub.2-C.sub.8)alkynyl, substituted (C.sub.1-C.sub.8)alkyl, substituted (C.sub.2-C.sub.8)alkenyl, or substituted (C.sub.2-C.sub.8)alkynyl, where each of these substituted radicals is substituted by one or more radicals from the group halogen, cyano, nitro, hydroxy, (C.sub.1-C.sub.6)alkoxy, (C.sub.2-C.sub.6)alkenyloxy, (C.sub.2-C.sub.6)alkynyloxy, (C.sub.1-C.sub.8)haloalkoxy, (C.sub.1-C.sub.4)alkoxy-(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.8)alkylthio, (C.sub.1-C.sub.8)haloalkylthio, (C.sub.1-C.sub.8)alkylsulfinyl, (C.sub.1-C.sub.8)haloalkylsulfinyl, (C.sub.1-C.sub.8)alkylsulfonyl, (C.sub.1-C.sub.8)haloalkylsulfonyl and tri-[(C.sub.1-C.sub.4)alkyl]silyl, and (ii) (C.sub.3-C.sub.8)cycloalkyl, (C.sub.5-C.sub.8)cycloalkenyl, (C.sub.5-C.sub.8)cycloalkynyl, phenyl, (C.sub.3-C.sub.8)cycloalkyl-(C.sub.1-C.sub.6)alkyl, (C.sub.5-C.sub.8)cycloalkenyl-(C.sub.1-C.sub.6)alkyl, (C.sub.5-C.sub.8)cycloalkynyl-(C.sub.1-C.sub.6)alkyl, phenyl-(C.sub.1-C.sub.6)alkyl, (C.sub.3-C.sub.8)cycloalkyloxy-(C.sub.1-C.sub.6)alkyl, (C.sub.3-C.sub.8)cycloalkyl-S(O).sub.p(C.sub.1-C.sub.6)alkyl, (C.sub.5-C.sub.8)cycloalkenyloxy-(C.sub.1-C.sub.6)alkyl, (C.sub.5-C.sub.8)cycloalkynyloxy-(C.sub.1-C.sub.6)alkyl, phenoxy-(C.sub.1-C.sub.6)alkyl, phenyl-S(O).sub.p(C.sub.1-C.sub.6)alkyl, (C.sub.3-C.sub.8)cycloalkylamino-(C.sub.1-C.sub.6)alkyl, (C.sub.5-C.sub.8)cycloalkenylamino-(C.sub.1-C.sub.6)alkyl, (C.sub.5-C.sub.8)cycloalkynylamino-(C.sub.1-C.sub.6)alkyl, phenylamino-(C.sub.1-C.sub.6)alkyl, Het.sup.1, Het.sup.1-(C.sub.1-C.sub.6)alkyl, Het.sup.1-O(C.sub.1-C.sub.6)alkyl or Het.sup.1-S(O).sub.p(C.sub.1-C.sub.6)alkyl, where Het.sup.1 has the meaning given above, and where each of these radicals is unsubstituted in the acyclic moiety or substituted by one or more identical or different radicals R.sup.A and in the cyclic moiety is unsubstituted or substituted by one or more identical or different radicals R.sup.B and p in each case represents 0, 1 or 2, where R.sup.A and R.sup.B in each case have the meaning given above, R.sup.aa has the meaning given above, and where R.sup.aa optionally independently is a radical selected from the group consisting of hydrogen, OH, (C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.4)haloalkyl, (C.sub.2-C.sub.6)alkenyl, (C.sub.2-C.sub.6)alkynyl, (C.sub.1-C.sub.6)alkoxy, (C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkyloxy, (C.sub.1-C.sub.4)haloalkoxy, (C.sub.1-C.sub.4)haloalkoxy-(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.4)haloalkoxy-(C.sub.1-C.sub.6)alkoxy, (C.sub.3-C.sub.6)alkenyloxy, (C.sub.3-C.sub.6)alkenyloxy-(C.sub.1-C.sub.6)alkyl, (C.sub.3-C.sub.6)alkenyloxy-(C.sub.1-C.sub.6)alkoxy, (C.sub.3-C.sub.6)alkynyloxy, (C.sub.3-C.sub.6)alkynyloxy-(C.sub.1-C.sub.6)alkyl, (C.sub.3-C.sub.6)alkynyloxy-(C.sub.1-C.sub.6)alkoxy, NR*R**, where R* and R** are as defined above, tri[(C.sub.1-C.sub.4)alkyl]silyl, tri[(C.sub.1-C.sub.4)alkyl]silyl-(C.sub.1-C.sub.6)alkyl, tri[(C.sub.1-C.sub.4)alkyl]silyl-(C.sub.1-C.sub.6)alkoxy, (C.sub.3-C.sub.6)cycloalkyl, (C.sub.3-C.sub.6)cycloalkoxy, (C.sub.3-C.sub.6)cycloalkyl-(C.sub.1-C.sub.8)alkyl, (C.sub.3-C.sub.6)cycloalkyl-(C.sub.1-C.sub.8)alkoxy, (C.sub.5-C.sub.6)cycloalkenyl, (C.sub.5-C.sub.6)cycloalkenyl-(C.sub.1-C.sub.6)alkyl, (C.sub.5-C.sub.6)cycloalkenyloxy, (C.sub.5-C.sub.6)cycloalkynyl, (C.sub.5-C.sub.6)cycloalkynyl-(C.sub.1-C.sub.6)alkyl, (C.sub.5-C.sub.6)cycloalkynyl-(C.sub.1-C.sub.6)alkoxy, phenyl, phenyl-(C.sub.1-C.sub.6)alkyl, phenyl-(C.sub.1-C.sub.6)alkoxy, phenoxy, phenoxy-(C.sub.1-C.sub.6)alkyl, phenoxy-(C.sub.1-C.sub.6)alkoxy, phenylthio, phenyl-S(O).sub.p(C.sub.1-C.sub.6)alkyl, phenyl-S(O).sub.p(C.sub.1-C.sub.6)alkoxy, where p in each case independently of one another is 0, 1 or 2, phenylamino, phenylamino-(C.sub.1-C.sub.6)alkyl, phenylamino-(C.sub.1-C.sub.6)alkoxy or a 5- or 6-membered monocyclic or 9- or 10-membered bicyclic heterocycle optionally bonded via an alkylene group or an alkoxy group, containing 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S, where each of the specified cyclic radicals R.sup.aa in the cyclic moiety is optionally substituted by one or more identical or different radicals selected from the group consisting of halogen, (C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4)haloalkyl, (C.sub.1-C.sub.4)alkoxy and (C.sub.1-C.sub.4)haloalkoxy.
8. The compound of formula (I) and/or salt thereof as claimed in claim 1, wherein (R.sup.2).sub.n represents n substituents R.sup.2, where R.sup.2 (if n=1) or each of the substituents R.sup.2 (if n is greater than 1) independently of the others represents halogen, cyano, nitro, (C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkoxy, (C.sub.1-C.sub.6)alkylthio, (C.sub.1-C.sub.6)alkylsulfinyl, (C.sub.1-C.sub.6)alkylsulfonyl, (C.sub.1-C.sub.6)haloalkyl, (C.sub.2-C.sub.6)haloalkenyl, (C.sub.1-C.sub.6)haloalkoxy, (C.sub.1-C.sub.6)haloalkylthio, (C.sub.1-C.sub.6)haloalkylsulfinyl, (C.sub.1-C.sub.6)haloalkylsulfonyl, (C.sub.2-C.sub.6)alkenyl, (C.sub.2-C.sub.6)alkynyl, tri[(C.sub.1-C.sub.4)alkyl]silyl or tri[(C.sub.1-C.sub.4)alkyl]silyl-(C.sub.1-C.sub.4)alkyl, and/or (R.sup.3).sub.m represents m substituents R.sup.3, where R.sup.3 (if m=1) or each of the substituents R.sup.3 (if m is greater than 1) independently of one another represents halogen, cyano, nitro, (C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkoxy, (C.sub.1-C.sub.6)alkylthio, (C.sub.1-C.sub.6)alkylsulfinyl, (C.sub.1-C.sub.6)alkylsulfonyl, (C.sub.1-C.sub.6)haloalkyl, (C.sub.2-C.sub.6)haloalkenyl, (C.sub.1-C.sub.6)haloalkoxy, (C.sub.1-C.sub.6)haloalkylthio, (C.sub.1-C.sub.6)haloalkylsulfinyl, (C.sub.1-C.sub.6)haloalkylsulfonyl, (C.sub.2-C.sub.6)alkenyl, (C.sub.2-C.sub.6)alkynyl, NR*R**, tri[(C.sub.1-C.sub.4)alkyl]silyl or tri[(C.sub.1-C.sub.4)alkyl]silyl(C.sub.1-C.sub.4)alkyl or where in each case two groups R.sup.3 directly adjacent on the ring together represent a group of the formula Z.sup.3-A**-Z.sup.4, in which A** represents an alkylene group having 1 to 4 carbon atoms which is optionally substituted by one or more radicals from the group consisting of halogen, (C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4)haloalkyl, (C.sub.1-C.sub.4)alkoxy and (C.sub.1-C.sub.4)haloalkoxy, Z.sup.3 represents a direct bond, O or S and Z.sup.4 represents a direct bond, O or S, where the group Z.sup.3-A**-Z.sup.4 together with the carbon atoms, bonded to the group, of the phenyl ring form a fused-on 5- or 6-membered ring, R*, R** each independently of one another or together with the nitrogen atom have the meaning mentioned above and n, m in each case independently of one another represent 0, 1, 2, 3, 4 or 5, optionally 0, 1, 2 or 3, optionally 0, 1 or 2.
9. The compound of formula (I) and/or salt thereof as claimed in claim 1, wherein (R.sup.2).sub.n represents n substituents R.sup.2, where, in the case that n=1, the substituent R.sup.2 or, in the case that n is greater than 1, each of the substituents R.sup.2 independently of the others represents halogen, cyano, nitro, (C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4)alkoxy, (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)haloalkyl, (C.sub.2-C.sub.4)haloalkenyl, (C.sub.1-C.sub.4)haloalkoxy, (C.sub.1-C.sub.4)haloalkylthio, (C.sub.1-C.sub.4)haloalkylsulfinyl, (C.sub.1-C.sub.4)haloalkylsulfonyl, (C.sub.2-C.sub.4)alkenyl, (C.sub.2-C.sub.4)alkynyl, tri[(C.sub.1-C.sub.4)alkyl]silyl or tri[(C.sub.1-C.sub.4)alkyl]silyl(C.sub.1-C.sub.4)alkyl, and n represents 0, 1, 2, 3, or 4, optionally 0, 1, 2 or 3, optionally in particular 0, 1 or 2.
10. The compound of formula (I) and/or salt thereof as claimed in claim 1, wherein (R.sup.3).sub.m represents m substituents R.sup.3, where in the case that m=1, the substituent R.sup.3 or, in the case that m is greater than 1, each of the substituents R.sup.3 independently of one another represents halogen, cyano, nitro, (C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4)alkoxy, (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)haloalkyl, (C.sub.2-C.sub.4)haloalkenyl, (C.sub.1-C.sub.4)haloalkoxy, (C.sub.1-C.sub.4)haloalkylthio, (C.sub.1-C.sub.4)haloalkylsulfinyl, (C.sub.1-C.sub.4)haloalkylsulfonyl, (C.sub.2-C.sub.6)alkenyl, (C.sub.2-C.sub.6)alkynyl or tri[(C.sub.1-C.sub.4)alkyl]silyl-Z.sup.b, where Z.sup.b=is a covalent bond or (C.sub.1-C.sub.4)alkylene, or in each case two groups R.sup.3 directly adjacent to one another at the ring together represent a group of the formula Z.sup.3-A**-Z.sup.4, where A** represents an alkylene group which is optionally substituted by one or more radicals from the group halogen, (C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4)haloalkyl, (C.sub.1-C.sub.4)alkoxy and (C.sub.1-C.sub.4)haloalkoxy, Z.sup.3 represents O or S and Z.sup.4 represents O or S, where the group Z.sup.3-A**-Z.sup.4 together with the carbon atoms, attached to the group, of the phenyl ring form a fused-on 5- or 6-membered ring, m represents 0, 1, 2, 3, 4 or 5, optionally 0, 1, 2, 3 or 4, optionally 0, 1, 2 or 3.
11. The compound of formula (I) and/or salt thereof as claimed in claim 1, wherein (R.sup.2).sub.n represents n substituents R.sup.2, where, in the case that n=1, the substituent R.sup.2 or, in the case that n is greater than 1, each of the substituents R.sup.2 independently of one another represents fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, methoxy, methylthio, methylsulfinyl, methylsulfonyl, trifluoromethyl, trifluoromethoxy, trifluoroalkylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, and (R.sup.3).sub.m represents m substituents R.sup.3, where, in the case that m=1, the substituent R.sup.3 or, in the case that m is greater than 1, each of the substituents R.sup.3 independently of the others represents fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, methoxy, methylthio, methylsulfinyl, methylsulfonyl, trifluoromethyl, trifluoromethoxy, trifluoroalkylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, and m represents 0, 1, 2, 3 or 4, optionally 0, 1, 2 or 3, and n represents 0, 1, 2 or 3, optionally 0, 1 or 2.
12. A product comprising a compound of formula (I) and/or salt thereof as defined in claim 1, that is a herbicide and/or plant growth regulator, optionally for crops of useful plants and/or ornamental plants.
13. A herbicidal or plant growth-regulating composition, wherein the composition comprises one or more compounds of the formula (I) and/or salts thereof as defined in claim 1, and one or more further substances selected from groups (i) and/or (ii): (i) one or more further agrochemically active substances, optionally selected from the group consisting of insecticides, acaricides, nematicides, further herbicides, fungicides, safeners, fertilizers and/or further growth regulators, (ii) one or more formulation auxiliaries customary in crop protection.
14. A method for controlling one or more harmful plants or for regulating the growth of plants, comprising applying an effective amount of one or more compounds of the formula (I) and/or salts thereof, as defined in claim 1, of a composition as claimed in claim 13, to the plants, seeds of plants, the soil in which or on which the plants grow or an area under cultivation.
15. A process for preparing a compound of formula (I) or salt as defined in claim 1, comprising converting a compound of formula (E) ##STR00016## by reduction into a compound of the formula (Ia) ##STR00017## and the compound (Ia) is optionally reacted further to give a compound of the formula (I), provided R.sup.1 in formula (I) does not represent hydrogen, where R represents hydrogen or an organic radical, optionally a radical selected from the group of the radicals defined for R.sup.1.
Description
SYNTHESIS EXAMPLES
1a) Preparation of methyl 4-(5-chloro-6-fluoropyridin-3-yl)-4-cyano-3-(2,5-difluorophenyl)butanoate
[0347] Under protective gas (argon), 293 mg (2.612 mmol) of potassium tert-butoxide were added to 2.228 g (13.061 mmol) of methyl 3-(2,6-difluorophenyl)acrylate and 2.381 g (12.016 mmol) of (5-chloro-6-fluoropyridin-3-yl)acetonitrile in 20.0 ml of toluene and 2 ml of DMF, and the mixture was stirred at 60 C. for 20 h. After removal of the solvent under reduced pressure, the residue was taken up in ethyl acetate and washed twice with in each case 50 ml of water. The combined organic phases were dried over sodium sulfate and the solvent was removed under reduced pressure. Chromatography of the residue over silica gel (ethyl acetate/heptane=15:85) gave 2.900 g (61% of theory) of the diastereomeric methyl 4-(5-chloro-6-fluoropyridin-3-yl)-4-cyano-3-(2,5-difluorophenyl)butanoates (erythro:threo=55:45, comparison of the doublet in .sup.1H-NMR in CDCl.sub.3 at 4.58 and 4.21 ppm).
1b) Preparation of 2-(5-chloro-6-fluoropyridin-3-yl)-3-(2,5-difluorophenyl)-5-hydroxypentanenitrile
[0348] Under protective gas (Ar), 2.9 g (7.87 mmol) of methyl 4-(5-chloro-6-fluoropyridin-3-yl)-4-cyano-3-(2,5-difluorophenyl)butanoate from synthesis example 1a) in 10 ml of THF were added to 0.848 g (15.73 mmol) of potassium borohydride and 0.333 g (7.87 mmol) of lithium chloride in 5 ml of THF, and the mixture was stirred at 70 C. for 5 h. After cooling to 0 C., water was added. The residue was then taken up in ethyl acetate and washed twice with in each case 50 ml of water. The combined organic phases were dried over sodium sulfate and the solvent was removed under reduced pressure. Chromatography of the residue over silica gel (ethyl acetate/heptane=15:85) gave 1.700 g (64% of theory) of the diastereomeric 2-(5-chloro-6-fluoropyridin-3-yl)-3-(2,5-difluorophenyl)-5-hydroxypentanenitriles (erythro:threo=57:43, comparison of the doublet in .sup.1H-NMR in CDCl.sub.3 at 4.38 and 4.15 ppm).
1c) Preparation of (2R,3R)-2-(5-chloro-6-fluoropyridin-3-yl)-3-(2,5-difluorophenyl)-5-hydroxypentanenitrile
[0349] Preparative chromatography [(80 ml/min n-heptane/2-propanol (80:20)] of 100 mg of the diastereomer mixture obtained according to synthesis example 1b) above (dissolved in 4.0 ml of methanol) on a chiral solid phase column [Chiralpak IC, 20 m, (25050) mm column] gave 7 mg of (2R,3R)-2-(5-chloro-6-fluoropyridin-3-yl)-3-(2,5-difluorophenyl)-5-hydroxypentanenitrile which eluted as the last of the four stereoisomers (retention time: 13.0 min). The absolute configuration was then assigned by X-ray structural analysis.
2a) Preparation of methyl 4-cyano-3-(2,6-difluorophenyl)-4-(3-thienyl)butanoate
[0350] Under protective gas (Ar), 182 mg (1.624 mmol) of potassium tert-butoxide were added to 1.609 g (8.118 mmol) of methyl 3-(2,6-difluorophenyl)acrylate and 1.000 g (8.118 mmol) of 3-thienylacetonitrile in 45.0 ml of toluene and 2 ml of DMF, and the mixture was stirred at 60 C. for 6 h. After removal of the solvent under reduced pressure, the residue was taken up in ethyl acetate and washed twice with in each case 50 ml of water. The combined organic phases were dried over sodium sulfate and the solvent was removed under reduced pressure. Chromatography of the residue over silica gel (ethyl acetate/heptane=15:85) gave 1.750 g (68% of theory) of the diastereomeric methyl 4-cyano-3-(2,6-difluorophenyl)-4-(3-thienyl)butanoates (erythro:threo=24:76, comparison of the doublet in .sup.1H-NMR in CDCl.sub.3 at 4.33 and 4.16 ppm).
2b) Preparation of 3-(2,6-difluorophenyl)-5-hydroxy-2-(3-thienyl)pentanenitrile
[0351] Under protective gas (Ar), 0.100 g (0.311 mmol) of methyl 4-cyano-3-(2,6-difluorophenyl)-4-(3-thienyl)butanoate in 2 ml THF were added to 0.017 g (0.311 mmol) of potassium borohydride and 0.013 g (0.311 mmol) of lithium chloride in 1 ml of THF, and the mixture was stirred at 70 C. for 5 h. After cooling to 0 C., water was added. The residue was then taken up in ethyl acetate and washed twice with in each case 50 ml of water. The combined organic phases were dried over sodium sulfate and the solvent was removed under reduced pressure. Chromatography of the residue over silica gel (ethyl acetate/heptane=15:85) gave 0.044 g (45% of theory) of the diastereomeric 3-(2,6-difluorophenyl)-5-hydroxy-2-(3-thienyl)pentanenitriles (erythro:threo=59:41, comparison of the doublet in .sup.1H-NMR in CDCl.sub.3 at 6.92 and 6.76 ppm).
[0352] Definition and Description of Preferred Compounds According to the InventionAnalytical and Physical Data
[0353] Information regarding the examples given in Tables 4a to 4d:
[0354] In Tables 4a to 4d below, the compounds according to the invention are assigned corresponding individual numbers (=example numbers), where the particular example number is composed of the compound number of the chemical formula (I), which refers to the same number as given in the respective line of Tables 1 to 3, followed by the respective stereoisomeric form. The particular stereoisomeric form corresponds to the above-defined formulae (I threo-1), (I threo-2), (I erythro-1) and (I erythro-2), or mixtures of these stereoisomers.
[0355] The same applies to the assignment of racemic or optically active threo stereoisomers or erythro stereoisomers of the compounds according to the invention.
[0356] In this way, the stereoisomers are given the respective clearly defined chemical structure of a compound of the formula (I) according to the invention, which the following examples aim to illustrate:
[0357] The compound name 1 threo-2 identifies the threo-2 isomers of the compound of the formula (I) [corresponding to formula I (I threo-2)], in which R.sup.1H (=hydrogen), and Q(R.sup.2).sub.n=6-fluoropyridin-3-yl and (R.sup.3).sub.m, =2,6-F.sub.2 according to entry number 1 from Table 1.
[0358] The compound name 14 erythro-1 identifies the erythro-1 isomers of the compound of the formula (I) [corresponding to formula I (I erythro-1)], in which R.sup.1H (=hydrogen), and Q(R.sup.2).sub.n=5-chloro-6-fluoropyridin-3-yl and (R.sup.3).sub.m=2,6-F.sub.2 according to entry number 14 from Table 1.
[0359] The compound name 85 erythro identifies a mixture of the erythro isomers of the compound of the formula (I) in which R.sup.1H (=hydrogen), and Q(R.sup.2).sub.n=pyridin-3-yl and (R.sup.3).sub.m=2,6-F.sub.2 according to entry number 85 from Table 1.
[0360] The compound name 460 threo-2 identifies the threo-2 isomers of the compound of the formula (I) [corresponding to formula (I threo-2)], in which R.sup.1H (=hydrogen), and Q(R.sup.2).sub.n=6-chloropyridin-3-yl and (R.sup.3).sub.m=2,5-F.sub.2 according to entry number 460 from Table 1.
[0361] The compound name 472 erythro-2 identifies the erythro-2 isomers of the compound of the formula (I) [corresponding to formula (I erythro-2)], in which R.sup.1H (=hydrogen), and Q(R.sup.2).sub.n=5-chloro-6-fluoropyridin-3-yl and (R.sup.3).sub.m=2,5-F.sub.2 according to entry number 472 from Table 1.
[0362] Tables 4a to 4d: Preferred compounds of the formulae (I threo-1), (I threo-2), (I erytro-1) and (I erytro-2) according to the invention
TABLE-US-00004 TABLE 4a Preferred (I threo-1) enantiomers
[0363] Table 4a describes the compounds of the formulae (1 threo-1) to (3981 threo-1), in which the structure combination of the groups R, Q(R.sup.2).sub.n and (R.sup.3).sub.m is defined according to a line number from Tables 1 to 3, as explained in detail above.
[0364] Table 4b: Preferred (I Threo-2) Enantiomers
[0365] Table 4b describes the compounds of the formulae (1 threo-2) to (3981 threo-2), in which the structure combination of the groups R, Q(R.sup.2).sub.n and (R.sup.3).sub.m is defined according to a line number from Tables 1 to 3, as explained in detail above.
TABLE-US-00005 TABLE 4c Preferred (I erythro-1) enantiomers
[0366] Table 4c describes the compounds of the formulae (1 erythro-1) to (3981 erythro-1), in which the structure combination of the groups R, Q(R.sup.2).sub.n and (R.sup.3).sub.m is defined according to a line number from Tables 1 to 3, as explained in detail above.
[0367] Table 4d: Preferred (I erythro-2) Enantiomers
[0368] Table 4d describes the compounds of the formulae (1 erythro-2) to (3981 erythro-2), in which the structure combination of the groups R, Q(R.sup.2).sub.n and (R.sup.3).sub.m is defined according to a line number from Tables 1 to 3, as explained in detail above.
[0369] Physical Data of Some Compounds According to the Invention:
[0370] Test Methods: [0371] 1) NMR=.sup.1H-NMR data (400 MHz, CDCl.sub.3); characteristic chemical shifts [in ppm] are given for the respective example. [0372] 2) HPLC=High Performance Liquid Chromatography, column: Zorbax Eclipse, 503.0, C18 1.8 m, mobile phase: water+0.06% formic acid/acrylonitrile+0.06% formic acid, gradient: 90:10, after 2 min 5:95; detector: DAD (210-400 nm); retention time (Rt) indicated for the example in question, [0373] 3) chiral HPLC=HPLC on a chiral column, column: Chiralpak IC, 2504.6 mm, 5 m DAIC 83325, detector wavelength: 210 nm; column temperature 25 C., [0374] mobile phase a: (n-heptane:2-propanol), (60:40), Chromasolv, flow rate: 1.0 ml/min [0375] mobile phase b: (n-heptane:2-propanol), (70:30), Chromasolv, flow rate: 1.0 ml/min [0376] mobile phase c: (n-heptane:2-propanol), (80:20), Chromasolv, flow rate: 1.0 ml/min [0377] mobile phase d: (n-heptane:2-propanol), (90:10), Chromasolv, flow rate: 0.6 ml/min
[0378] NMR Data of Selected Examples
[0379] .sup.1H-NMR data (CDCl.sub.3)chemical shift of selected characteristic signals in ppm.
[0380] NMR Peak List Method
[0381] The 1H-NMR data of selected examples are noted in the form of 1H-NMR peak lists. For each signal peak, first the value in ppm and then the signal intensity in round brackets are listed. The pairs of value-signal intensity numbers for different signal peaks are listed with separation from one another by semicolons.
[0382] The peak list for one example therefore has the form:
.sub.1 (intensity.sub.1); .sub.2 (intensity.sub.2); . . . ; .sub.i(intensity.sub.i); . . . ; .sub.n (intensity.sub.n)
[0383] 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.
[0384] Calibration of the chemical shift of 1H NMR spectra is accomplished using tetramethylsilane and/or the chemical shift of the solvent, particularly in the case of spectra which are measured in DMSO. Therefore, the tetramethylsilane peak may but need not occur in NMR peak lists.
[0385] The lists of the 1H-NMR peaks are similar to the classic 1H-NMR prints and thus usually comprise all peaks listed in classic NMR interpretations.
[0386] In addition, like classic 1H-NMR prints, they may show solvent signals, signals of stereoisomers of the target compounds, which are likewise part of the subject matter of the invention, and/or peaks of impurities.
[0387] When stating compound signals in the delta range of solvents and/or water, in our lists of 1H NMR peaks, the usual solvent peaks, for example peaks of DMSO in DMSO-D.sub.6 and the peak of water are shown, which usually have on average a high intensity.
[0388] 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%).
[0389] Such stereoisomers and/or impurities may be typical of the particular preparation process. Their peaks can thus help in identifying reproduction of our preparation process with reference to by-product fingerprints.
[0390] 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 relevant peak picking in classical 1H-NMR interpretation.
[0391] Further details of 1H NMR peak lists can be found in the Research Disclosure Database Number 564025.
[0392] Example 186: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =7.519 (1.1); 7.397 (5.8); 7.390 (6.9); 7.385 (6.4); 7.377 (7.5); 7.314 (6.6); 7.313 (6.6); 7.310 (7.2); 7.309 (7.0); 7.306 (5.6); 7.305 (5.7); 7.303 (5.8); 7.302 (5.7); 7.299 (3.9); 7.294 (2.4); 7.283 (2.3); 7.278 (7.4); 7.273 (2.9); 7.2703 (1.4); 7.2695 (1.4); 7.269 (1.5); 7.268 (1.7); 7.267 (2.0); 7.266 (2.3); 7.265 (2.7); 7.260 (182.9); 7.254 (1.6); 7.253 (1.0); 7.2524 (0.7); 7.2516 (0.6); 7.241 (1.9); 7.226 (0.7); 7.187 (6.4); 7.180 (7.4); 7.175 (7.1); 7.171 (2.5); 7.168 (8.1); 7.155 (4.0); 7.148 (8.5); 7.145 (7.6); 7.139 (2.6); 7.134 (10.2); 7.132 (8.2); 7.129 (2.8); 7.118 (3.0); 7.113 (4.3); 7.097 (2.1); 7.055 (5.9); 7.051 (6.5); 7.047 (5.6); 7.044 (5.5); 6.996 (1.1); 6.962 (3.3); 6.958 (7.3); 6.941 (3.4); 6.936 (11.6); 6.931 (3.7); 6.920 (7.1); 6.916 (9.8); 6.910 (3.7); 6.907 (6.4); 6.904 (6.0); 6.788 (3.0); 6.784 (7.6); 6.762 (12.2); 6.741 (6.5); 5.298 (2.6); 4.407 (7.5); 4.380 (16.0); 4.352 (9.3); 3.908 (1.6); 3.898 (1.6); 3.880 (2.8); 3.870 (2.8); 3.852 (2.8); 3.841 (2.7); 3.824 (2.6); 3.813 (2.6); 3.797 (1.4); 3.787 (1.3); 3.705 (1.5); 3.693 (1.8); 3.689 (1.8); 3.677 (3.3); 3.666 (2.3); 3.662 (2.3); 3.650 (1.9); 3.552 (1.3); 3.541 (1.6); 3.536 (1.6); 3.525 (3.1); 3.514 (2.1); 3.509 (2.2); 3.497 (2.7); 3.482 (1.8); 3.473 (2.0); 3.460 (2.0); 3.446 (1.4); 3.432 (1.3); 3.388 (1.5); 3.375 (1.7); 3.366 (1.9); 3.352 (1.8); 3.340 (1.3); 3.326 (1.1); 2.512 (1.0); 2.502 (1.1); 2.496 (1.1); 2.489 (1.2); 2.486 (1.3); 2.478 (1.9); 2.467 (1.6); 2.462 (1.9); 2.455 (1.7); 2.452 (1.7); 2.445 (1.5); 2.439 (1.4); 2.429 (1.3); 2.302 (0.5); 2.299 (1.0); 2.295 (0.6); 2.288 (1.4); 2.285 (1.4); 2.278 (0.7); 2.274 (1.3); 2.270 (1.4); 2.257 (1.8); 2.253 (1.6); 2.246 (1.2); 2.240 (1.1); 2.236 (1.0); 2.224 (0.9); 2.222 (0.9); 2.211 (0.6); 2.045 (0.6); 2.033 (0.8); 2.031 (0.9); 2.020 (0.8); 2.014 (0.9); 2.010 (1.2); 2.006 (1.3); 2.003 (1.4); 1.999 (1.6); 1.996 (1.5); 1.993 (1.1); 1.985 (1.3); 1.983 (1.3); 1.971 (1.3); 1.969 (1.3); 1.961 (0.6); 1.958 (0.8); 1.894 (1.2); 1.883 (1.3); 1.878 (1.4); 1.872 (1.4); 1.867 (1.5); 1.861 (1.9); 1.857 (1.4); 1.845 (1.9); 1.838 (1.0); 1.833 (0.9); 1.827 (0.9); 1.822 (0.8); 1.811 (0.7); 1.556 (0.7); 1.284 (1.1); 1.255 (1.1); 1.216 (1.0); 1.201 (1.0); 0.008 (1.9); 0.000 (64.4); 0.006 (0.6); 0.009 (1.8)
[0393] Example 86: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =8.667 (5.4); 8.665 (5.8); 8.663 (6.2); 8.660 (5.6); 8.655 (5.7); 8.653 (6.2); 8.650 (6.1); 8.648 (5.5); 8.486 (5.5); 8.483 (5.9); 8.481 (5.9); 8.479 (5.6); 8.474 (5.5); 8.471 (6.1); 8.469 (5.9); 8.467 (5.4); 7.764 (5.0); 7.760 (5.1); 7.745 (10.3); 7.740 (10.1); 7.726 (6.4); 7.721 (6.2); 7.558 (5.2); 7.553 (5.1); 7.539 (9.8); 7.534 (9.9); 7.519 (10.3); 7.515 (6.2); 7.430 (6.4); 7.428 (11.9); 7.425 (6.9); 7.411 (5.9); 7.408 (10.7); 7.406 (6.2); 7.321 (6.8); 7.318 (6.7); 7.314 (2.8); 7.309 (7.0); 7.306 (6.9); 7.302 (6.7); 7.299 (8.0); 7.293 (4.4); 7.290 (6.9); 7.287 (6.5); 7.282 (4.0); 7.277 (11.6); 7.272 (6.4); 7.271 (6.0); 7.260 (1049.0); 7.248 (1.8); 7.240 (3.1); 7.160 (9.0); 7.140 (14.7); 7.138 (11.7); 7.128 (7.0); 7.126 (6.2); 7.121 (10.3); 7.119 (6.2); 7.116 (4.2); 7.109 (6.4); 7.107 (5.9); 7.100 (9.7); 7.095 (3.0); 7.084 (3.6); 7.079 (5.2); 7.063 (2.6); 6.996 (6.0); 6.961 (4.4); 6.956 (9.7); 6.939 (4.6); 6.935 (16.0); 6.930 (4.9); 6.913 (8.4); 6.909 (4.1); 6.748 (9.5); 6.726 (15.8); 6.705 (8.2); 4.527 (11.0); 4.502 (12.6); 4.450 (12.9); 4.423 (15.2); 4.140 (2.0); 4.129 (3.6); 4.114 (4.2); 102 (6.9); 4.090 (4.0); 4.075 (3.4); 4.064 (1.9); 3.726 (1.0); 3.714 (2.1); 3.698 (3.3); 3.686 (3.8); 3.671 (2.7); 3.658 (1.4); 3.549 (1.9); 3.535 (3.8); 3.522 (5.2); 3.510 (5.5); 3.498 (4.3); 3.485 (2.4); 3.471 (1.1); 3.428 (1.3); 3.414 (2.6); 3.400 (2.6); 3.394 (2.8); 3.379 (2.4); 3.366 (1.8); 3.352 (0.9); 2.555 (1.3); 2.544 (1.4); 2.539 (1.2); 2.533 (1.4); 2.528 (1.5); 2.521 (2.4); 2.505 (2.3); 2.499 (2.0); 2.494 (1.9); 2.488 (1.9); 2.483 (1.7); 2.472 (1.5); 2.344 (1.3); 2.331 (1.7); 2.316 (1.7); 2.303 (2.0); 2.269 (1.3); 2.257 (0.8); 2.108 (1.1); 2.095 (1.4); 2.081 (1.9); 2.059 (2.2); 2.047 (2.1); 2.034 (1.8); 2.020 (1.0); 1.830 (1.5); 1.814 (1.9); 1.809 (1.8); 1.803 (1.8); 1.797 (2.4); 1.781 (2.4); 1.768 (1.4); 1.763 (1.3); 1.747 (1.1); 1.548 (123.1); 1.440 (3.8); 1.426 (7.2); 1.408 (7.8); 1.394 (3.6); 0.146 (1.2); 0.069 (1.5); 0.008 (12.7); 0.007 (4.5); 0.006 (4.7); 0.000 (409.7); 0.007 (2.9); 0.009 (10.9); 0.150 (1.2)
[0394] Example 544: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =8.606 (6.1); 8.603 (6.9); 8.601 (7.2); 8.599 (6.7); 8.594 (6.9); 8.589 (10.5); 8.587 (10.3); 8.583 (6.0); 8.578 (5.4); 8.576 (6.0); 8.574 (5.9); 8.571 (5.4); 7.662 (5.8); 7.658 (6.1); 7.656 (5.5); 7.651 (5.3); 7.643 (11.6); 7.639 (12.3); 7.636 (10.9); 7.632 (9.7); 7.624 (7.2); 7.619 (7.2); 7.617 (6.6); 7.612 (5.9); 7.519 (2.8); 7.311 (0.6); 7.294 (0.7); 7.292 (0.5); 7.269 (10.2); 7.266 (17.4); 7.260 (483.9); 7.254 (10.4); 7.250 (7.8); 7.247 (11.3); 7.245 (9.9); 7.238 (6.6); 7.235 (8.1); 7.231 (5.4); 7.221 (5.6); 7.219 (5.3); 7.215 (5.6); 7.212 (5.1); 7.207 (7.4); 7.205 (12.6); 7.203 (11.7); 7.200 (5.5); 7.188 (6.6); 7.185 (11.3); 7.183 (7.0); 7.173 (3.8); 7.167 (3.8); 7.159 (6.2); 7.151 (3.3); 7.144 (3.7); 7.137 (3.5); 7.000 (2.0); 6.996 (3.1); 6.988 (2.7); 6.976 (5.1); 6.964 (5.1); 6.960 (2.2); 6.956 (1.5); 6.952 (5.2); 6.945 (3.5); 6.940 (7.7); 6.933 (6.1); 6.930 (5.1); 6.923 (12.6); 6.916 (6.3); 6.913 (10.9); 6.911 (11.6); 6.902 (12.8); 6.894 (7.4); 6.890 (8.4); 6.885 (10.0); 6.878 (6.1); 6.877 (6.0); 6.871 (3.1); 6.866 (7.6); 4.487 (15.1); 4.468 (16.0); 4.337 (12.5); 4.319 (13.9); 3.997 (2.0); 3.986 (2.2); 3.978 (2.0); 3.969 (3.4); 3.957 (3.8); 3.939 (5.2); 3.920 (3.8); 3.900 (2.0); 3.667 (3.4); 3.654 (4.7); 3.640 (5.7); 3.627 (4.0); 3.547 (1.6); 3.530 (2.8); 3.516 (2.4); 3.485 (1.8); 3.461 (2.0); 2.313 (1.1); 2.301 (1.3); 2.297 (1.2); 2.291 (1.1); 2.286 (1.4); 2.278 (2.8); 2.262 (2.7); 2.256 (2.5); 2.251 (2.4); 2.245 (2.4); 2.241 (2.3); 2.229 (1.9); 2.213 (1.4); 2.210 (1.4); 2.199 (2.8); 2.185 (2.6); 2.172 (2.7); 2.161 (2.1); 2.150 (1.3); 2.137 (1.4); 2.123 (0.7); 2.116 (0.6); 2.102 (1.2); 2.080 (3.1); 2.066 (5.0); 2.060 (4.7); 2.053 (2.8); 2.046 (9.6); 2.031 (5.4); 2.027 (6.2); 2.012 (3.5); 1.992 (1.3); 1.977 (0.6); 1.664 (2.6); 1.586 (30.1); 0.146 (0.5); 0.008 (5.6); 0.000 (194.5); 0.009 (5.5); 0.150 (0.6)
[0395] Example 472: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =7.902 (11.4); 7.897 (12.9); 7.893 (11.5); 7.860 (8.0); 7.855 (9.9); 7.851 (9.2); 7.791 (9.4); 7.785 (7.9); 7.771 (9.3); 7.765 (8.0); 7.581 (10.3); 7.575 (10.4); 7.560 (10.4); 7.554 (9.9); 7.519 (9.9); 7.310 (1.1); 7.295 (1.4); 7.292 (2.6); 7.287 (2.3); 7.260 (1776.8); 7.227 (1.6); 7.210 (1.4); 7.188 (4.9); 7.181 (5.6); 7.174 (5.3); 7.167 (9.6); 7.159 (5.1); 7.153 (4.7); 7.145 (5.1); 7.034 (2.5); 7.026 (3.3); 7.023 (3.4); 7.018 (3.1); 7.015 (4.2); 7.011 (7.7); 7.007 (5.9); 7.003 (6.9); 7.000 (10.3); 6.996 (15.7); 6.993 (6.7); 6.989 (7.9); 6.985 (11.3); 6.977 (11.9); 6.972 (6.1); 6.967 (6.5); 6.964 (9.3); 6.960 (9.8); 6.957 (5.2); 6.954 (5.7); 6.949 (9.5); 6.946 (6.0); 6.942 (3.9); 6.938 (10.9); 6.926 (11.1); 6.915 (4.0); 6.903 (3.6); 6.870 (3.7); 6.863 (3.3); 6.856 (3.6); 6.849 (6.5); 6.841 (3.5); 6.835 (3.8); 6.828 (2.9); 4.387 (15.1); 4.370 (16.0); 4.156 (10.9); 4.134 (11.7); 4.012 (3.1); 3.983 (2.9); 3.749 (4.9); 3.732 (6.7); 3.710 (7.3); 3.695 (4.5); 3.651 (2.3); 3.642 (2.4); 3.622 (4.0); 3.601 (2.5); 3.592 (2.8); 3.555 (3.4); 3.435 (1.9); 3.422 (2.5); 3.410 (2.9); 2.370 (1.6); 2.361 (1.9); 2.356 (1.9); 2.347 (3.2); 2.336 (3.0); 2.326 (2.8); 2.321 (3.2); 2.312 (4.8); 2.302 (2.6); 2.297 (2.2); 2.288 (2.1); 2.189 (1.5); 2.179 (2.8); 2.160 (2.9); 2.139 (5.5); 2.126 (6.8); 2.119 (7.7); 2.111 (4.9); 2.105 (11.0); 2.092 (5.9); 2.083 (6.2); 2.070 (3.8); 2.059 (1.4); 2.048 (1.6); 2.035 (1.0); 1.541 (201.2); 1.378 (5.3); 1.285 (4.0); 0.146 (1.7); 0.008 (18.2); 0.000 (636.7); 0.009 (17.1); 0.149 (1.7)
[0396] Example 2043: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =8.647 (7.4); 8.644 (7.7); 8.635 (8.0); 8.631 (7.8); 8.600 (8.4); 8.596 (8.6); 8.484 (8.5); 8.480 (8.8); 8.472 (9.1); 8.468 (8.8); 8.305 (8.6); 8.299 (8.7); 7.783 (3.4); 7.778 (4.2); 7.777 (4.2); 7.773 (3.5); 7.763 (4.0); 7.759 (4.7); 7.757 (4.8); 7.753 (3.8); 7.679 (3.6); 7.674 (4.7); 7.669 (3.6); 7.659 (4.2); 7.654 (5.2); 7.649 (3.9); 7.521 (1.0); 7.397 (4.7); 7.395 (4.7); 7.385 (4.9); 7.383 (4.8); 7.377 (4.6); 7.375 (4.4); 7.365 (4.5); 7.363 (4.3); 7.262 (164.2); 7.258 (9.2); 7.256 (8.0); 7.246 (6.6); 7.244 (6.4); 7.238 (6.0); 7.236 (5.8); 7.226 (5.5); 7.224 (5.3); 7.183 (2.3); 7.170 (2.3); 7.160 (4.5); 7.147 (4.5); 7.138 (4.6); 7.125 (4.5); 7.115 (2.2); 7.102 (2.0); 7.010 (1.8); 6.998 (2.2); 6.987 (4.5); 6.975 (4.6); 6.965 (4.7); 6.952 (4.7); 6.942 (2.3); 6.929 (3.1); 6.925 (2.3); 6.921 (2.2); 6.915 (2.1); 6.907 (3.3); 6.901 (3.5); 6.897 (3.4); 6.892 (3.3); 6.883 (1.9); 6.878 (1.9); 6.874 (1.8); 6.868 (1.7); 6.741 (1.6); 6.735 (1.9); 6.731 (1.8); 6.726 (1.8); 6.717 (2.9); 6.712 (3.2); 6.708 (3.2); 6.702 (2.9); 6.694 (1.7); 6.688 (1.7); 6.684 (1.6); 6.679 (1.5); 5.299 (16.0); 4.326 (8.6); 4.301 (9.7); 4.253 (9.4); 4.225 (11.4); 4.129 (0.5); 4.111 (0.5); 3.963 (1.9); 3.953 (2.0); 3.934 (3.6); 3.925 (3.7); 3.906 (1.9); 3.896 (2.0); 3.887 (2.0); 3.876 (2.0); 3.860 (3.3); 3.849 (3.3); 3.834 (1.9); 3.822 (1.8); 3.745 (2.3); 3.735 (2.5); 3.586 (2.0); 3.576 (2.2); 3.486 (1.7); 3.474 (2.1); 3.462 (2.5); 3.449 (2.0); 3.436 (1.6); 3.395 (1.6); 3.383 (2.0); 3.372 (2.3); 3.346 (1.4); 2.588 (1.2); 2.578 (1.3); 2.573 (1.4); 2.564 (2.1); 2.554 (2.6); 2.540 (2.5); 2.530 (2.9); 2.520 (1.9); 2.516 (1.8); 2.506 (1.6); 2.341 (1.1); 2.330 (1.9); 2.318 (1.5); 2.313 (1.5); 2.301 (2.4); 2.295 (2.2); 2.290 (1.8); 2.283 (1.4); 2.267 (1.6); 2.255 (0.9); 2.096 (0.7); 2.084 (1.3); 2.072 (1.1); 2.068 (1.2); 2.061 (1.8); 2.057 (1.9); 2.053 (1.9); 2.049 (2.3); 2.045 (1.9); 2.042 (2.6); 2.037 (1.6); 2.034 (1.6); 2.022 (1.9); 2.010 (1.0); 1.875 (1.2); 1.862 (1.7); 1.851 (1.8); 1.841 (2.6); 1.827 (2.5); 1.817 (1.5); 1.806 (1.4); 1.792 (1.0); 1.620 (7.1); 1.528 (3.2); 1.429 (2.9); 1.276 (0.6); 1.258 (1.2); 1.240 (0.7); 0.070 (0.6); 0.008 (2.3); 0.000 (68.2); 0.009 (2.4)
[0397] Example 1: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =8.191 (7.6); 8.185 (7.9); 7.892 (8.9); 7.885 (9.5); 7.875 (4.2); 7.869 (3.9); 7.857 (4.2); 7.854 (4.6); 7.851 (4.3); 7.847 (4.3); 7.836 (4.2); 7.829 (4.0); 7.773 (4.6); 7.767 (4.1); 7.755 (5.1); 7.752 (5.5); 7.749 (4.8); 7.746 (4.6); 7.734 (4.8); 7.727 (4.3); 7.519 (8.2); 7.341 (2.4); 7.325 (4.9); 7.320 (4.3); 7.310 (2.0); 7.309 (3.3); 7.304 (9.7); 7.299 (3.2); 7.296 (1.4); 7.292 (4.2); 7.288 (5.3); 7.287 (4.8); 7.286 (2.8); 7.283 (7.0); 7.281 (3.5); 7.280 (2.9); 7.2793 (3.0); 7.2785 (2.8); 7.278 (3.0); 7.277 (3.5); 7.276 (3.9); 7.2753 (4.1); 7.2745 (4.3); 7.274 (4.9); 7.273 (5.2); 7.272 (5.5); 7.2713 (6.4); 7.2705 (6.6); 7.270 (7.4); 7.269 (8.2); 7.268 (10.3); 7.2673 (12.5); 7.2665 (15.5); 7.266 (16.2); 7.265 (18.8); 7.264 (24.5); 7.263 (33.5); 7.260 (1439.5); 7.2544 (9.1); 7.2535 (6.3); 7.253 (5.2); 7.252 (4.1); 7.251 (3.7); 7.2503 (3.2); 7.2495 (2.7); 7.249 (1.7); 7.248 (2.7); 7.247 (1.7); 7.2463 (1.2); 7.2455 (1.1); 7.245 (1.0); 7.244 (1.0); 7.243 (0.9); 7.242 (1.1); 7.240 (0.7); 7.225 (1.5); 7.210 (1.0); 7.190 (3.1); 7.174 (6.0); 7.169 (6.0); 7.158 (3.5); 7.153 (12.5); 7.148 (3.6); 7.137 (5.5); 7.132 (6.5); 7.116 (3.6); 7.020 (5.7); 7.013 (5.7); 6.999 (5.7); 6.996 (9.3); 6.992 (5.5); 6.970 (4.2); 6.966 (9.0); 6.949 (4.7); 6.944 (14.7); 6.940 (4.8); 6.923 (7.7); 6.918 (3.8); 6.870 (7.3); 6.862 (7.3); 6.849 (7.0); 6.841 (6.9); 6.787 (9.6); 6.766 (16.0); 6.744 (8.4); 4.356 (10.3); 4.331 (11.3); 4.279 (13.2); 4.250 (15.2); 3.956 (1.1); 3.923 (2.5); 3.913 (2.6); 3.894 (4.4); 3.884 (4.5); 3.866 (2.2); 3.856 (3.5); 3.847 (2.1); 3.831 (3.1); 3.821 (3.0); 3.806 (1.8); 3.795 (1.8); 3.708 (2.9); 3.582 (2.2); 3.460 (2.6); 3.384 (2.1); 2.574 (1.8); 2.564 (1.9); 2.558 (1.9); 2.549 (2.7); 2.539 (3.3); 2.525 (3.3); 2.515 (3.5); 2.506 (2.1); 2.501 (2.3); 2.491 (1.9); 2.330 (1.5); 2.319 (2.5); 2.291 (2.8); 2.255 (1.6); 2.093 (1.6); 2.066 (2.1); 2.058 (2.3); 2.046 (1.7); 2.031 (2.0); 2.019 (1.1); 1.878 (1.4); 1.866 (1.9); 1.853 (1.9); 1.844 (2.8); 1.830 (2.7); 1.821 (1.5); 1.808 (1.4); 1.795 (1.0); 1.541 (122.4); 1.305 (3.3); 1.228 (2.7); 0.146 (1.4); 0.032 (1.4); 0.022 (0.9); 0.019 (0.9); 0.0144 (1.4); 0.0136 (1.7); 0.013 (1.9); 0.0112 (2.7); 0.0105 (2.8); 0.008 (16.5); 0.007 (5.5); 0.006 (5.6); 0.005 (6.8); 0.004 (8.8); 0.000 (520.2); 0.007 (3.2); 0.009 (13.3); 0.150 (1.5)
[0398] Example 6: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =8.522 (15.1); 8.517 (15.2); 8.209 (11.9); 8.204 (12.0); 7.788 (8.7); 7.783 (16.0); 7.778 (8.2); 7.521 (0.7); 7.274 (0.7); 7.272 (0.9); 7.262 (140.8); 7.206 (2.3); 7.190 (4.7); 7.185 (4.4); 7.174 (2.8); 7.169 (9.7); 7.164 (3.0); 7.153 (4.5); 7.148 (5.4); 7.132 (2.7); 6.998 (0.8); 6.808 (8.7); 6.786 (14.6); 6.765 (7.8); 5.299 (14.2); 4.244 (12.2); 4.216 (14.4); 3.922 (2.1); 3.912 (2.2); 3.894 (3.9); 3.884 (3.9); 3.866 (1.9); 3.856 (1.8); 3.749 (2.7); 3.738 (3.2); 3.734 (3.2); 3.723 (5.3); 3.711 (4.0); 3.707 (3.9); 3.696 (3.3); 3.623 (0.5); 3.488 (2.9); 3.475 (3.2); 3.464 (3.4); 3.460 (2.9); 3.452 (3.5); 3.448 (2.9); 3.437 (2.6); 3.425 (2.5); 2.558 (1.3); 2.548 (1.5); 2.543 (1.5); 2.534 (2.2); 2.524 (2.9); 2.513 (2.2); 2.509 (2.9); 2.500 (2.9); 2.490 (1.9); 2.486 (1.8); 2.476 (1.6); 2.340 (0.7); 2.336 (1.2); 2.333 (0.9); 2.325 (2.0); 2.317 (0.9); 2.313 (1.5); 2.308 (1.6); 2.301 (1.8); 2.296 (2.4); 2.291 (2.1); 2.285 (1.7); 2.279 (1.2); 2.274 (1.1); 2.270 (0.6); 2.262 (1.4); 2.254 (0.6); 2.250 (0.8); 1.507 (1.5); 1.432 (0.6); 1.333 (0.6); 1.284 (0.8); 1.255 (0.9); 0.008 (1.7); 0.000 (50.1); 0.009 (1.3)
[0399] Example 2005: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =8.519 (9.5); 8.513 (9.5); 8.436 (5.2); 8.432 (7.6); 8.428 (4.9); 8.364 (11.1); 8.358 (11.1); 8.261 (1.9); 8.254 (1.9); 8.146 (2.2); 8.141 (5.8); 8.137 (8.0); 7.520 (3.7); 7.514 (3.4); 7.508 (2.6); 7.498 (2.8); 7.493 (3.4); 7.487 (2.6); 7.425 (3.0); 7.419 (3.8); 7.414 (2.9); 7.403 (3.1); 7.398 (3.8); 7.392 (2.8); 7.280 (0.5); 7.279 (0.5); 7.278 (0.5); 7.2772 (0.6); 7.2765 (0.6); 7.276 (0.7); 7.275 (0.7); 7.274 (0.8); 7.2733 (0.9); 7.2725 (1.0); 7.272 (1.0); 7.271 (1.2); 7.270 (1.4); 7.2693 (1.7); 7.2685 (1.9); 7.268 (2.1); 7.267 (2.6); 7.266 (3.1); 7.265 (4.0); 7.261 (180.7); 7.257 (2.0); 7.2563 (1.3); 7.2555 (0.9); 7.255 (0.6); 7.211 (1.1); 7.197 (1.3); 7.184 (1.4); 7.180 (0.7); 7.174 (3.9); 7.161 (3.4); 7.151 (3.8); 7.148 (1.1); 7.139 (3.3); 7.128 (1.5); 7.116 (1.4); 7.045 (1.5); 7.033 (1.5); 7.022 (3.8); 7.010 (4.0); 7.000 (3.9); 6.997 (2.2); 6.987 (4.3); 6.977 (1.8); 6.974 (1.0); 6.964 (2.3); 6.952 (0.8); 6.939 (1.4); 6.933 (1.5); 6.929 (1.7); 6.924 (1.4); 6.915 (2.3); 6.910 (2.5); 6.906 (2.4); 6.900 (2.3); 6.892 (1.2); 6.886 (1.3); 6.882 (1.1); 6.877 (1.1); 6.774 (1.4); 6.769 (1.6); 6.765 (1.6); 6.759 (1.5); 6.751 (2.5); 6.745 (2.8); 6.741 (2.7); 6.736 (2.5); 6.727 (1.3); 6.722 (1.4); 6.718 (1.3); 6.712 (1.2); 5.298 (16.0); 4.389 (5.4); 4.364 (5.9); 4.307 (5.6); 4.279 (6.5); 3.964 (1.5); 3.954 (1.5); 3.936 (2.8); 3.926 (2.8); 3.908 (1.4); 3.897 (2.3); 3.884 (1.3); 3.870 (2.3); 3.858 (2.3); 3.844 (1.2); 3.832 (1.2); 3.778 (1.9); 3.767 (2.4); 3.764 (2.4); 3.751 (3.5); 3.739 (2.9); 3.736 (2.8); 3.725 (2.3); 3.676 (0.7); 3.664 (1.1); 3.649 (1.2); 3.641 (1.8); 3.636 (0.9); 3.629 (2.3); 3.627 (2.4); 3.615 (3.3); 3.602 (2.7); 3.600 (2.7); 3.589 (2.0); 3.523 (0.5); 3.517 (0.6); 3.503 (0.6); 3.491 (2.2); 3.479 (2.2); 3.468 (2.4); 3.464 (2.0); 3.456 (2.4); 3.452 (2.1); 3.441 (1.8); 3.429 (2.1); 3.426 (2.0); 3.414 (1.9); 3.402 (2.1); 3.398 (1.7); 3.391 (2.1); 3.387 (1.7); 3.376 (1.5); 3.364 (1.5); 3.109 (1.3); 3.093 (1.0); 3.082 (0.8); 2.578 (1.0); 2.568 (1.1); 2.564 (1.1); 2.554 (1.8); 2.544 (2.0); 2.530 (2.0); 2.520 (2.4); 2.510 (1.4); 2.506 (1.3); 2.496 (1.2); 2.336 (0.8); 2.333 (0.6); 2.329 (1.0); 2.325 (1.6); 2.321 (1.0); 2.317 (0.6); 2.313 (1.0); 2.308 (1.0); 2.305 (0.9); 2.301 (1.4); 2.297 (1.9); 2.294 (1.6); 2.290 (1.7); 2.286 (1.4); 2.279 (0.8); 2.274 (0.8); 2.266 (0.7); 2.262 (1.2); 2.258 (0.7); 2.251 (0.6); 2.169 (2.0); 2.108 (1.0); 2.103 (0.8); 2.099 (1.2); 2.095 (1.0); 2.088 (1.1); 2.084 (1.0); 2.076 (1.6); 2.073 (2.0); 2.068 (1.4); 2.065 (1.8); 2.061 (1.6); 2.057 (1.1); 2.053 (1.2); 2.049 (1.1); 2.041 (1.0); 2.038 (1.6); 2.026 (0.7); 1.893 (0.9); 1.880 (1.4); 1.869 (1.4); 1.858 (2.0); 1.845 (1.8); 1.834 (1.0); 1.823 (1.0); 1.810 (0.7); 1.469 (1.3); 0.008 (2.4); 0.007 (0.8); 0.006 (0.9); 0.005 (1.0); 0.004 (1.4); 0.002 (3.4); 0.000 (78.2); 0.005 (1.0); 0.006 (0.7); 0.007 (0.9); 0.009 (2.1); 0.050 (0.5)
[0400] Example 1834: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =8.181 (14.2); 8.175 (14.0); 8.141 (9.2); 8.135 (9.2); 7.519 (7.0); 7.515 (4.4); 7.509 (4.0); 7.495 (11.3); 7.488 (11.7); 7.470 (15.3); 7.468 (16.0); 7.449 (6.4); 7.446 (13.4); 7.445 (12.9); 7.425 (17.0); 7.424 (17.3); 7.350 (1.2); 7.336 (0.9); 7.319 (11.2); 7.312 (11.2); 7.298 (8.6); 7.291 (8.5); 7.282 (1.8); 7.277 (2.9); 7.275 (3.6); 7.274 (3.8); 7.272 (4.4); 7.2713 (4.6); 7.2705 (5.4); 7.270 (5.8); 7.269 (6.8); 7.267 (9.5); 7.2664 (10.9); 7.2656 (12.8); 7.260 (1195.3); 7.251 (2.8); 7.228 (2.2); 7.225 (3.1); 7.210 (6.3); 7.204 (4.5); 7.200 (3.8); 7.191 (4.9); 7.171 (2.7); 7.159 (3.0); 7.150 (9.0); 7.143 (6.8); 7.138 (6.5); 7.134 (12.2); 7.127 (5.6); 7.120 (9.9); 7.118 (9.2); 7.114 (7.3); 7.106 (2.5); 7.102 (5.0); 7.098 (7.5); 7.093 (4.7); 7.079 (4.1); 7.074 (5.3); 7.069 (3.5); 7.063 (3.3); 7.060 (3.1); 7.056 (3.7); 7.050 (4.9); 7.044 (3.6); 7.041 (3.7); 7.031 (3.6); 7.028 (4.0); 7.020 (1.7); 7.007 (1.5); 6.996 (6.9); 6.903 (3.6); 6.888 (4.4); 6.884 (4.7); 6.870 (2.6); 4.339 (14.4); 4.322 (15.5); 4.135 (10.8); 4.113 (12.0); 3.796 (3.0); 3.780 (5.6); 3.774 (3.9); 3.758 (7.4); 3.747 (6.8); 3.741 (3.9); 3.733 (6.6); 3.720 (7.9); 3.707 (7.1); 3.693 (5.1); 3.682 (6.2); 3.670 (3.6); 3.665 (5.0); 3.655 (4.8); 3.542 (3.2); 3.529 (3.5); 3.522 (3.7); 3.515 (3.2); 3.509 (3.9); 3.502 (3.0); 3.495 (2.8); 3.482 (2.8); 3.422 (2.1); 3.410 (2.3); 3.399 (2.8); 3.386 (3.0); 3.372 (1.9); 3.360 (1.8); 2.375 (1.4); 2.366 (1.3); 2.361 (1.3); 2.351 (2.1); 2.341 (2.7); 2.326 (2.4); 2.317 (3.4); 2.308 (2.0); 2.303 (2.0); 2.293 (1.7); 2.221 (1.4); 2.209 (2.4); 2.181 (3.0); 2.170 (2.5); 2.146 (4.8); 2.132 (7.8); 2.125 (4.5); 2.119 (6.9); 2.110 (7.5); 2.097 (8.0); 2.085 (3.4); 2.063 (1.1); 1.539 (19.6); 1.345 (1.6); 0.157 (1.0); 0.146 (1.4); 0.008 (14.2); 0.006 (5.2); 0.000 (453.3); 0.009 (12.1); 0.150 (1.4)
[0401] Example 5: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =8.593 (12.3); 8.588 (12.6); 8.471 (13.0); 8.466 (13.1); 8.433 (0.7); 8.420 (14.2); 8.415 (14.5); 8.341 (0.6); 8.335 (0.6); 8.182 (1.2); 8.171 (13.3); 8.167 (13.7); 7.744 (7.9); 7.738 (13.9); 7.733 (7.5); 7.640 (8.3); 7.635 (14.9); 7.630 (8.1); 7.520 (0.7); 7.415 (0.6); 7.348 (1.7); 7.332 (3.4); 7.327 (3.5); 7.311 (6.9); 7.306 (2.8); 7.295 (3.6); 7.290 (4.2); 7.274 (3.0); 7.261 (115.5); 7.201 (1.9); 7.185 (3.8); 7.181 (4.0); 7.169 (2.7); 7.164 (7.8); 7.160 (3.0); 7.148 (4.2); 7.143 (4.4); 7.127 (2.2); 6.997 (0.8); 6.972 (9.2); 6.950 (15.0); 6.928 (8.1); 6.818 (0.9); 6.804 (9.8); 6.782 (16.0); 6.760 (8.4); 5.298 (0.8); 4.346 (10.9); 4.321 (12.0); 4.263 (12.4); 4.235 (14.6); 3.927 (2.6); 3.917 (2.7); 3.899 (4.8); 3.889 (4.8); 3.870 (4.2); 3.859 (3.8); 3.843 (3.8); 3.832 (3.8); 3.817 (2.1); 3.805 (2.1); 3.747 (3.1); 3.736 (3.8); 3.733 (3.8); 3.721 (6.2); 3.709 (4.6); 3.706 (4.6); 3.694 (3.8); 3.622 (2.8); 3.610 (3.6); 3.595 (5.7); 3.583 (4.5); 3.569 (3.3); 3.487 (3.4); 3.475 (3.6); 3.464 (4.2); 3.452 (4.2); 3.437 (3.1); 3.424 (4.2); 3.409 (3.3); 3.399 (3.7); 3.387 (3.6); 3.372 (2.5); 3.360 (2.4); 3.063 (0.9); 3.043 (0.7); 2.559 (1.5); 2.549 (1.7); 2.544 (1.8); 2.535 (2.7); 2.525 (3.4); 2.511 (3.4); 2.501 (3.5); 2.492 (2.2); 2.487 (2.1); 2.477 (1.8); 2.337 (1.4); 2.326 (2.5); 2.309 (2.1); 2.297 (3.2); 2.263 (1.8); 2.251 (1.0); 2.112 (1.0); 2.101 (1.8); 2.086 (1.6); 2.074 (2.5); 2.066 (2.9); 2.054 (2.0); 2.039 (2.2); 2.028 (1.2); 1.876 (1.6); 1.862 (2.3); 1.851 (2.2); 1.841 (3.4); 1.828 (3.1); 1.819 (1.8); 1.807 (1.7); 1.793 (1.1); 1.501 (4.0); 1.256 (0.5); 0.007 (1.9); 0.000 (44.2)
[0402] Example 6: (erythro): .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =8.693 (12.8); 8.688 (13.6); 8.507 (12.5); 8.502 (13.3); 7.888 (8.5); 7.883 (15.5); 7.878 (9.2); 7.520 (0.7); 7.349 (2.4); 7.333 (4.5); 7.328 (4.3); 7.317 (3.3); 7.312 (8.7); 7.307 (4.1); 7.296 (4.5); 7.291 (5.8); 7.275 (3.8); 7.261 (105.8); 7.228 (1.2); 6.997 (1.1); 6.973 (9.8); 6.951 (16.0); 6.929 (8.8); 5.298 (7.5); 4.327 (11.1); 4.302 (12.3); 3.862 (2.3); 3.851 (2.5); 3.836 (4.1); 3.824 (4.3); 3.821 (4.6); 3.811 (2.5); 3.799 (2.4); 3.727 (1.0); 3.623 (2.7); 3.618 (2.2); 3.608 (3.8); 3.596 (5.8); 3.584 (4.5); 3.581 (4.7); 3.570 (3.6); 3.564 (1.7); 3.423 (2.9); 3.410 (3.3); 3.400 (3.8); 3.388 (3.8); 3.384 (3.4); 3.373 (2.8); 3.361 (2.5); 2.112 (1.2); 2.100 (2.0); 2.088 (1.8); 2.084 (1.9); 2.077 (2.5); 2.073 (2.8); 2.069 (2.8); 2.065 (3.2); 2.057 (2.1); 2.053 (2.4); 2.050 (2.3); 2.038 (2.5); 2.026 (1.5); 1.877 (1.7); 1.863 (2.5); 1.852 (2.5); 1.843 (3.6); 1.829 (3.4); 1.821 (2.1); 1.808 (2.0); 1.794 (1.4); 1.476 (1.5); 1.333 (1.2); 1.284 (1.2); 1.256 (1.3); 0.008 (1.7); 0.000 (38.0); 0.009 (2.2)
[0403] Example 472 (erythro): .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =7.901 (5.1); 7.897 (6.0); 7.893 (5.1); 7.582 (4.3); 7.576 (4.1); 7.561 (4.2); 7.555 (4.0); 7.261 (64.3); 7.187 (2.0); 7.180 (2.3); 7.174 (2.3); 7.166 (4.0); 7.158 (2.3); 7.152 (2.1); 7.144 (2.1); 7.025 (1.1); 7.017 (1.1); 7.015 (1.4); 7.007 (2.1); 7.002 (2.3); 6.995 (2.8); 6.992 (2.5); 6.989 (1.6); 6.984 (3.7); 6.976 (2.4); 6.974 (2.4); 6.966 (2.1); 6.960 (3.3); 6.948 (3.4); 6.937 (4.4); 6.926 (4.3); 6.914 (1.8); 6.903 (1.5); 5.299 (16.0); 4.389 (6.5); 4.373 (6.8); 3.821 (0.8); 3.794 (1.8); 3.781 (3.7); 3.768 (3.8); 3.760 (1.9); 3.754 (4.8); 3.741 (2.7); 3.731 (2.5); 3.710 (2.4); 3.694 (1.2); 3.579 (2.0); 3.567 (2.2); 3.559 (2.3); 3.552 (2.0); 3.546 (2.4); 3.540 (1.9); 3.532 (1.8); 3.519 (1.7); 2.159 (0.7); 2.153 (0.5); 2.145 (0.7); 2.138 (1.9); 2.124 (2.7); 2.117 (3.0); 2.109 (2.2); 2.104 (4.7); 2.090 (2.8); 2.082 (2.9); 2.069 (1.8); 2.057 (0.7); 2.044 (1.1); 1.484 (1.5); 1.432 (0.9); 1.258 (0.8); 0.008 (0.9); 0.000 (23.0); 0.009 (0.8)
[0404] Example 3: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =8.339 (3.4); 8.333 (3.3); 8.042 (4.3); 8.035 (4.3); 7.627 (2.2); 7.620 (2.1); 7.606 (4.0); 7.600 (3.9); 7.559 (4.8); 7.558 (4.8); 7.538 (2.6); 7.537 (2.6); 7.523 (3.0); 7.520 (1.1); 7.517 (2.9); 7.503 (4.2); 7.496 (4.1); 7.413 (5.8); 7.412 (5.8); 7.393 (4.0); 7.392 (4.0); 7.341 (0.9); 7.325 (1.6); 7.320 (1.4); 7.309 (1.0); 7.304 (3.2); 7.299 (1.2); 7.288 (1.4); 7.283 (1.9); 7.274 (0.5); 7.267 (2.1); 7.261 (106.6); 7.203 (1.0); 7.187 (2.0); 7.182 (1.9); 7.171 (1.2); 7.166 (4.1); 7.161 (1.3); 7.150 (1.9); 7.145 (2.2); 7.129 (1.1); 6.997 (0.6); 6.970 (1.6); 6.966 (3.4); 6.949 (1.6); 6.944 (5.4); 6.939 (1.7); 6.922 (2.9); 6.918 (1.4); 6.798 (3.8); 6.776 (6.3); 6.755 (3.4); 5.298 (16.0); 4.318 (3.9); 4.293 (4.4); 4.248 (5.0); 4.220 (5.9); 3.919 (0.9); 3.910 (0.9); 3.891 (1.7); 3.881 (1.7); 3.863 (0.8); 3.852 (1.3); 3.840 (0.7); 3.824 (1.3); 3.814 (1.2); 3.799 (0.7); 3.788 (0.7); 3.740 (1.1); 3.730 (1.4); 3.726 (1.4); 3.714 (2.3); 3.702 (1.6); 3.698 (1.6); 3.688 (1.4); 3.618 (0.9); 3.607 (1.1); 3.604 (1.1); 3.592 (1.8); 3.580 (1.4); 3.577 (1.4); 3.565 (1.1); 3.478 (1.2); 3.466 (1.3); 3.455 (1.4); 3.451 (1.2); 3.443 (1.4); 3.439 (1.2); 3.428 (1.1); 3.416 (1.1); 3.410 (1.0); 3.397 (1.0); 3.387 (1.1); 3.383 (0.9); 3.375 (1.1); 3.371 (0.9); 3.360 (0.8); 3.348 (0.8); 2.560 (0.6); 2.551 (0.7); 2.546 (0.7); 2.537 (1.0); 2.527 (1.2); 2.516 (0.9); 2.512 (1.2); 2.502 (1.3); 2.493 (0.9); 2.488 (0.8); 2.478 (0.7); 2.321 (0.6); 2.309 (0.9); 2.297 (0.7); 2.293 (0.7); 2.280 (1.1); 2.270 (0.8); 2.263 (0.5); 2.258 (0.5); 2.246 (0.6); 2.085 (0.6); 2.062 (0.7); 2.058 (0.8); 2.054 (0.7); 2.050 (0.9); 2.047 (0.7); 2.039 (0.6); 2.035 (0.6); 2.023 (0.7); 1.865 (0.5); 1.851 (0.7); 1.840 (0.7); 1.830 (1.1); 1.816 (1.0); 1.806 (0.6); 1.796 (0.6); 1.476 (0.7); 0.008 (1.2); 0.000 (41.0); 0.009 (1.2)
[0405] Example 1915: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =8.636 (3.0); 8.632 (3.2); 8.623 (3.2); 8.620 (3.1); 8.583 (3.3); 8.578 (3.4); 8.491 (3.6); 8.487 (3.8); 8.479 (3.8); 475 (3.7); 8.309 (3.6); 8.304 (3.7); 7.762 (1.4); 7.758 (1.7); 7.752 (1.4); 7.742 (1.6); 7.738 (1.7); 7.737 (1.9); 7.732 (1.5); 7.655 (1.5); 7.650 (1.9); 7.645 (1.5); 7.635 (1.7); 7.630 (2.1); 7.625 (1.6); 7.388 (1.9); 7.386 (1.9); 7.376 (1.9); 7.374 (1.9); 7.368 (1.8); 7.366 (1.8); 7.356 (1.7); 7.354 (1.7); 7.264 (53.3); 7.257 (2.7); 7.256 (2.6); 7.245 (2.3); 7.243 (2.3); 7.237 (2.2); 7.236 (2.1); 7.225 (2.0); 7.224 (2.0); 7.004 (2.1); 6.998 (5.3); 6.977 (5.2); 6.970 (2.1); 6.811 (2.0); 6.805 (5.5); 6.784 (5.5); 6.777 (2.0); 5.299 (16.0); 4.292 (3.5); 4.267 (3.8); 4.215 (3.9); 4.187 (4.7); 3.912 (0.8); 3.903 (0.9); 3.884 (1.5); 3.874 (1.5); 3.856 (0.8); 3.846 (0.8); 3.835 (0.7); 3.824 (0.8); 3.809 (1.2); 3.798 (1.2); 3.783 (0.7); 3.772 (0.7); 3.749 (0.6); 3.736 (1.0); 3.723 (1.2); 3.709 (1.1); 3.696 (0.7); 3.602 (0.5); 3.589 (0.8); 3.576 (1.0); 3.563 (1.0); 3.550 (0.6); 3.473 (0.6); 3.462 (0.7); 3.448 (0.9); 3.438 (0.9); 3.425 (0.6); 3.412 (0.5); 3.393 (0.6); 3.380 (0.6); 3.368 (0.8); 3.358 (0.8); 3.344 (0.5); 2.557 (0.5); 2.547 (0.6); 2.542 (0.6); 2.533 (0.9); 2.523 (1.1); 2.508 (1.1); 2.498 (1.1); 2.489 (0.7); 2.485 (0.7); 2.475 (0.6); 2.285 (0.8); 2.274 (0.6); 2.269 (0.6); 2.261 (0.7); 2.257 (1.0); 2.251 (0.9); 2.246 (0.7); 2.222 (0.6); 2.057 (0.6); 2.033 (0.7); 2.030 (0.8); 2.026 (0.7); 2.022 (0.9); 2.018 (0.7); 2.010 (0.6); 2.007 (0.6); 1.995 (0.7); 1.865 (0.5); 1.852 (0.7); 1.840 (0.7); 1.830 (1.1); 1.817 (1.0); 1.808 (0.5); 1.795 (0.5); 1.676 (0.7); 1.664 (0.7); 1.612 (1.0); 1.517 (0.7); 0.008 (0.5); 0.000 (18.1); 0.009 (0.6)
[0406] Example 1961: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =8.169 (14.3); 8.162 (14.3); 8.127 (9.5); 8.120 (9.6); 7.588 (6.7); 7.582 (6.6); 7.568 (7.7); 7.561 (7.5); 7.519 (4.3); 7.442 (4.1); 7.438 (4.4); 7.424 (8.1); 7.419 (8.7); 7.405 (5.0); 7.401 (5.0); 7.385 (7.8); 7.379 (7.6); 7.364 (10.5); 7.358 (10.3); 7.310 (1.6); 7.307 (3.1); 7.303 (3.4); 7.294 (3.8); 7.289 (6.7); 7.287 (5.1); 7.284 (6.2); 7.281 (13.5); 7.275 (7.3); 7.273 (6.3); 7.271 (8.5); 7.268 (11.9); 7.260 (814.9); 7.255 (29.0); 7.246 (4.7); 7.244 (5.4); 7.241 (4.2); 7.233 (15.1); 7.224 (4.0); 7.218 (2.5); 7.209 (9.4); 7.206 (8.7); 7.190 (10.9); 7.187 (11.5); 7.172 (4.7); 7.168 (4.3); 7.114 (1.0); 7.109 (1.5); 7.095 (5.3); 7.089 (4.9); 7.087 (5.3); 7.082 (11.6); 7.080 (10.0); 7.073 (5.1); 7.068 (6.2); 7.066 (6.1); 7.047 (1.5); 7.025 (4.1); 7.023 (3.7); 7.005 (3.8); 7.002 (3.8); 6.996 (7.9); 6.977 (3.6); 6.969 (6.2); 6.966 (6.2); 6.949 (5.4); 6.946 (6.4); 6.944 (7.0); 6.940 (6.4); 6.923 (5.3); 6.920 (5.1); 5.298 (3.6); 4.342 (15.2); 4.326 (16.0); 4.161 (9.9); 4.139 (10.9); 3.765 (2.9); 3.746 (7.6); 3.728 (8.3); 3.710 (5.4); 3.694 (3.1); 3.668 (2.4); 3.650 (3.7); 3.640 (3.6); 3.627 (2.3); 3.621 (3.1); 3.611 (2.7); 3.599 (2.4); 3.589 (2.2); 3.528 (3.1); 3.401 (1.9); 2.386 (1.2); 2.377 (1.2); 2.371 (1.3); 2.362 (1.9); 2.352 (2.4); 2.342 (2.0); 2.337 (2.4); 2.328 (2.6); 2.319 (2.0); 2.314 (1.9); 2.304 (1.8); 2.244 (1.1); 2.234 (2.2); 2.219 (1.4); 2.205 (2.3); 2.196 (1.7); 2.170 (1.7); 2.148 (6.3); 2.131 (10.9); 2.117 (10.2); 2.113 (8.7); 2.099 (5.8); 2.005 (0.6); 1.545 (84.7); 1.330 (4.2); 1.244 (2.4); 0.146 (1.0); 0.069 (1.8); 0.050 (0.5); 0.008 (8.7); 0.006 (3.1); 0.005 (3.3); 0.000 (316.2); 0.006 (3.1); 0.007 (2.7); 0.009 (9.2); 0.016 (0.7); 0.150 (0.9)
[0407] Example 1873: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =8.606 (1.4); 8.594 (1.7); 8.587 (2.1); 8.581 (2.1); 8.568 (8.6); 8.564 (9.2); 8.556 (9.6); 8.552 (9.5); 8.527 (7.1); 8.523 (7.7); 8.515 (7.8); 8.511 (7.7); 8.468 (0.5); 8.433 (10.7); 8.428 (10.9); 8.396 (8.6); 8.390 (8.8); 8.360 (1.0); 8.339 (0.7); 7.736 (1.0); 7.735 (1.0); 7.730 (0.8); 7.717 (1.1); 7.715 (1.1); 7.711 (0.8); 7.659 (3.6); 7.654 (4.7); 7.649 (3.6); 7.639 (3.9); 7.634 (5.1); 7.629 (3.8); 7.522 (1.5); 7.466 (4.1); 7.461 (5.6); 7.456 (4.3); 7.446 (5.0); 7.441 (6.6); 7.436 (4.7); 7.366 (1.7); 7.354 (1.6); 7.346 (1.5); 7.336 (1.2); 7.296 (1.6); 7.289 (5.9); 7.287 (6.2); 7.277 (6.8); 7.275 (7.3); 7.267 (10.2); 7.263 (254.9); 7.255 (8.6); 7.249 (8.0); 7.248 (7.9); 7.242 (6.9); 7.240 (6.8); 7.228 (8.5); 7.221 (3.3); 7.217 (3.3); 7.213 (6.6); 7.204 (4.0); 7.197 (3.8); 7.194 (5.2); 7.189 (3.7); 7.161 (3.0); 7.148 (3.2); 7.146 (3.1); 7.140 (6.0); 7.138 (6.5); 7.125 (10.1); 7.121 (9.1); 7.108 (8.1); 7.102 (7.4); 7.096 (5.4); 7.091 (2.8); 7.087 (4.2); 7.083 (5.4); 7.079 (4.8); 7.071 (3.9); 7.066 (4.5); 7.063 (4.0); 7.058 (2.6); 7.053 (4.0); 7.047 (5.4); 7.042 (6.1); 7.028 (6.6); 7.024 (7.1); 7.021 (4.9); 7.011 (4.4); 7.009 (4.4); 7.004 (2.1); 6.999 (2.8); 6.988 (2.0); 6.928 (2.3); 6.924 (3.6); 6.921 (2.5); 6.914 (2.4); 6.909 (3.7); 6.905 (4.7); 6.897 (1.9); 6.891 (2.5); 6.886 (1.6); 5.298 (16.0); 4.354 (12.8); 4.337 (13.5); 4.224 (0.7); 4.206 (0.7); 4.151 (9.7); 4.130 (10.8); 4.080 (0.5); 4.048 (0.6); 4.027 (0.5); 3.808 (3.0); 3.791 (5.4); 3.781 (8.2); 3.775 (3.9); 3.769 (5.8); 3.753 (3.2); 3.742 (3.3); 3.737 (3.9); 3.733 (3.7); 3.724 (7.4); 3.711 (9.7); 3.705 (4.0); 3.697 (8.5); 3.684 (6.8); 3.675 (3.5); 3.664 (5.3); 3.653 (3.8); 3.648 (3.7); 3.637 (3.3); 3.603 (0.8); 3.566 (1.5); 3.530 (3.7); 3.516 (3.9); 3.511 (4.3); 3.503 (3.5); 3.497 (4.2); 3.489 (3.3); 3.484 (3.4); 3.470 (3.1); 3.422 (2.7); 3.410 (3.0); 3.399 (3.3); 3.396 (2.9); 3.387 (3.2); 3.383 (2.9); 3.373 (2.5); 3.360 (2.3); 2.384 (1.2); 2.374 (1.3); 2.368 (1.4); 2.359 (1.8); 2.349 (2.5); 2.339 (2.2); 2.334 (2.5); 2.325 (2.9); 2.316 (2.2); 2.311 (2.1); 2.301 (1.9); 2.237 (1.4); 2.226 (2.5); 2.211 (1.7); 2.198 (2.7); 2.188 (2.1); 2.181 (1.6); 2.163 (2.2); 2.146 (3.7); 2.137 (3.7); 2.131 (6.0); 2.125 (7.9); 2.111 (7.8); 2.102 (6.1); 2.097 (3.9); 2.089 (3.5); 2.067 (1.2); 2.053 (0.9); 1.630 (4.5); 1.256 (0.9); 1.246 (0.8); 0.008 (2.6); 0.000 (85.9); 0.009 (3.0)
[0408] Example 1 (threo): .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =7.893 (9.0); 7.887 (9.7); 7.774 (4.6); 7.767 (4.2); 7.756 (5.1); 7.753 (5.6); 7.749 (5.0); 7.746 (4.9); 7.734 (4.7); 7.728 (4.3); 7.521 (0.8); 7.275 (0.5); 7.274 (0.5); 7.273 (0.7); 7.272 (0.7); 7.2712 (0.8); 7.2705 (1.0); 7.270 (1.1); 7.269 (1.3); 7.268 (1.5); 7.267 (1.8); 7.262 (128.4); 7.255 (0.6); 7.190 (2.7); 7.174 (5.6); 7.169 (5.3); 7.158 (3.2); 7.153 (11.5); 7.148 (3.6); 7.136 (5.3); 7.132 (6.3); 7.115 (3.1); 6.998 (0.8); 6.870 (7.3); 6.863 (7.4); 6.849 (7.0); 6.841 (6.9); 6.787 (9.6); 6.765 (16.0); 6.744 (8.5); 5.299 (3.6); 4.281 (13.0); 4.252 (15.1); 3.924 (2.4); 3.914 (2.5); 3.896 (4.6); 3.886 (4.6); 3.867 (2.2); 3.858 (2.1); 3.746 (3.2); 3.735 (3.8); 3.731 (3.9); 3.719 (6.5); 3.708 (4.7); 3.704 (4.6); 3.693 (4.1); 3.487 (3.5); 3.474 (3.8); 3.464 (4.1); 3.460 (3.4); 3.451 (4.1); 3.447 (3.6); 3.436 (3.2); 3.424 (3.1); 2.571 (1.6); 2.561 (1.8); 2.556 (1.8); 2.547 (2.6); 2.537 (3.3); 2.534 (2.1); 2.527 (2.5); 2.522 (3.3); 2.513 (3.4); 2.504 (2.3); 2.499 (2.1); 2.489 (1.9); 2.333 (0.8); 2.330 (1.4); 2.326 (1.0); 2.318 (2.2); 2.310 (1.0); 2.306 (1.8); 2.302 (1.8); 2.295 (2.0); 2.289 (2.7); 2.285 (2.5); 2.279 (2.0); 2.272 (1.5); 2.267 (1.3); 2.263 (0.8); 2.255 (1.6); 2.247 (0.7); 2.244 (1.0); 2.240 (0.6); 1.495 (2.9); 1.333 (0.6); 1.284 (0.9); 1.276 (0.6); 1.262 (0.6); 1.256 (1.2); 0.008 (1.5); 0.006 (0.6); 0.000 (45.7); 0.009 (1.2)
[0409] Example 2: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =8.358 (10.0); 8.352 (9.9); 8.058 (11.7); 8.052 (11.7); 7.730 (7.4); 7.724 (7.3); 7.710 (8.3); 7.703 (8.0); 7.627 (8.6); 7.620 (8.4); 7.606 (9.6); 7.600 (9.3); 7.519 (4.6); 7.405 (10.8); 7.384 (9.7); 7.373 (2.0); 7.342 (1.6); 7.326 (3.7); 7.321 (3.4); 7.310 (3.1); 7.305 (8.5); 7.300 (2.8); 7.294 (1.6); 7.288 (3.6); 7.284 (5.2); 7.260 (826.1); 7.238 (12.7); 7.228 (1.2); 7.209 (1.6); 7.200 (2.4); 7.184 (5.3); 7.179 (5.1); 7.167 (2.9); 7.162 (10.4); 7.158 (3.3); 7.146 (3.2); 7.141 (5.3); 7.125 (2.7); 6.996 (4.6); 6.967 (8.5); 6.945 (14.1); 6.923 (7.5); 6.919 (3.9); 6.796 (9.6); 6.774 (16.0); 6.752 (8.4); 5.299 (1.9); 4.337 (9.9); 4.313 (11.1); 4.266 (12.6); 4.237 (14.9); 3.922 (2.4); 3.912 (2.5); 3.893 (4.4); 3.884 (4.4); 3.865 (2.2); 3.856 (3.6); 3.845 (1.9); 3.829 (3.1); 3.818 (3.1); 3.804 (1.8); 3.793 (1.7); 3.746 (1.7); 3.731 (2.5); 3.719 (3.4); 3.707 (3.1); 3.693 (2.1); 3.608 (2.1); 3.595 (2.6); 3.582 (2.8); 3.569 (1.7); 3.447 (2.6); 3.420 (1.8); 3.388 (2.1); 2.567 (1.6); 2.557 (1.6); 2.552 (1.8); 2.543 (2.7); 2.533 (3.1); 2.518 (3.1); 2.509 (3.4); 2.500 (2.2); 2.495 (2.0); 2.485 (1.8); 2.326 (1.3); 2.314 (2.3); 2.285 (2.7); 2.251 (1.6); 2.090 (1.6); 2.055 (2.4); 2.040 (1.5); 2.028 (1.8); 2.016 (1.0); 2.005 (0.7); 1.869 (1.3); 1.856 (1.9); 1.844 (1.9); 1.835 (2.8); 1.821 (2.6); 1.812 (1.4); 1.799 (1.4); 1.786 (0.9); 1.540 (37.1); 1.300 (2.4); 1.227 (1.9); 0.157 (0.8); 0.146 (0.9); 0.113 (0.7); 0.008 (9.3); 0.000 (314.2); 0.009 (9.1); 0.051 (0.8); 0.150 (1.1)
[0410] Example 472 (erythro): .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =7.901 (5.1); 7.897 (6.0); 7.893 (5.1); 7.582 (4.3); 7.576 (4.1); 7.561 (4.2); 7.555 (4.0); 7.261 (64.3); 7.187 (2.0); 7.180 (2.3); 7.174 (2.3); 7.166 (4.0); 7.158 (2.3); 7.152 (2.1); 7.144 (2.1); 7.025 (1.1); 7.017 (1.1); 7.015 (1.4); 7.007 (2.1); 7.002 (2.3); 6.995 (2.8); 6.992 (2.5); 6.989 (1.6); 6.984 (3.7); 6.976 (2.4); 6.974 (2.4); 6.966 (2.1); 6.960 (3.3); 6.948 (3.4); 6.937 (4.4); 6.926 (4.3); 6.914 (1.8); 6.903 (1.5); 5.299 (16.0); 4.389 (6.5); 4.373 (6.8); 3.821 (0.8); 3.794 (1.8); 3.781 (3.7); 3.768 (3.8); 3.760 (1.9); 3.754 (4.8); 3.741 (2.7); 3.731 (2.5); 3.710 (2.4); 3.694 (1.2); 3.579 (2.0); 3.567 (2.2); 3.559 (2.3); 3.552 (2.0); 3.546 (2.4); 3.540 (1.9); 3.532 (1.8); 3.519 (1.7); 2.159 (0.7); 2.153 (0.5); 2.145 (0.7); 2.138 (1.9); 2.124 (2.7); 2.117 (3.0); 2.109 (2.2); 2.104 (4.7); 2.090 (2.8); 2.082 (2.9); 2.069 (1.8); 2.057 (0.7); 2.044 (1.1); 1.484 (1.5); 1.432 (0.9); 1.258 (0.8); 0.008 (0.9); 0.000 (23.0); 0.009 (0.8)
[0411] Example 472 (threo): .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =7.860 (11.4); 7.855 (14.7); 7.852 (13.0); 7.791 (12.3); 7.786 (10.6); 7.771 (12.1); 7.765 (10.7); 7.520 (1.3); 7.311 (0.5); 7.297 (0.9); 7.261 (212.8); 7.034 (3.4); 7.022 (3.9); 7.011 (9.6); 6.999 (9.9); 6.987 (8.1); 6.982 (5.9); 6.975 (11.5); 6.971 (6.6); 6.964 (9.9); 6.959 (3.5); 6.956 (6.0); 6.953 (6.9); 6.946 (5.7); 6.941 (4.2); 6.934 (2.9); 6.931 (2.1); 6.923 (2.2); 6.871 (5.0); 6.863 (4.7); 6.857 (5.4); 6.849 (9.0); 6.842 (4.9); 6.836 (5.2); 6.828 (4.3); 5.299 (5.5); 4.158 (14.7); 4.136 (16.0); 3.736 (4.3); 3.726 (5.2); 3.722 (5.4); 3.710 (7.4); 3.699 (6.2); 3.695 (6.0); 3.685 (5.1); 3.652 (3.3); 3.643 (3.5); 3.631 (3.7); 3.623 (5.8); 3.615 (4.0); 3.603 (3.6); 3.594 (3.5); 3.439 (4.7); 3.428 (5.4); 3.416 (6.1); 3.413 (5.5); 3.404 (6.1); 3.401 (5.6); 3.389 (4.5); 3.377 (4.2); 2.370 (2.2); 2.361 (2.4); 2.355 (2.5); 2.346 (4.3); 2.335 (4.5); 2.325 (3.8); 2.321 (4.5); 2.311 (6.0); 2.302 (3.5); 2.297 (3.2); 2.287 (2.8); 2.192 (2.0); 2.189 (2.1); 2.179 (3.7); 2.170 (2.4); 2.167 (2.4); 2.163 (2.4); 2.160 (2.4); 2.152 (4.2); 2.142 (3.8); 2.128 (1.7); 2.116 (2.5); 2.106 (1.4); 1.454 (1.6); 1.333 (1.4); 1.284 (1.4); 1.256 (1.9); 0.008 (2.7); 0.000 (76.0); 0.009 (2.9)
[0412] Example 543: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =8.573 (10.8); 8.569 (11.0); 8.561 (11.2); 8.557 (10.8); 8.535 (0.5); 8.531 (0.6); 8.523 (0.6); 8.519 (0.5); 8.449 (12.5); 8.444 (12.2); 8.405 (0.5); 8.399 (0.6); 7.520 (2.4); 7.493 (4.7); 7.488 (6.3); 7.483 (4.6); 7.473 (5.7); 7.468 (7.4); 7.463 (5.2); 7.345 (0.7); 7.293 (1.0); 7.261 (436.3); 7.255 (2.7); 7.252 (8.1); 7.250 (7.7); 7.244 (6.5); 7.242 (6.4); 7.232 (6.2); 7.230 (5.8); 7.159 (4.4); 7.151 (4.9); 7.145 (4.7); 7.137 (8.4); 7.129 (4.9); 7.123 (4.6); 7.116 (4.6); 6.997 (2.6); 6.987 (2.5); 6.979 (2.5); 6.977 (3.1); 6.969 (4.6); 6.964 (5.6); 6.961 (2.9); 6.957 (6.0); 6.954 (5.6); 6.951 (3.3); 6.946 (9.2); 6.939 (5.9); 6.936 (5.5); 6.928 (10.3); 6.916 (7.0); 6.904 (9.7); 6.893 (9.4); 6.882 (3.5); 6.870 (3.2); 5.299 (2.3); 4.334 (15.1); 4.316 (16.0); 4.148 (0.6); 4.127 (0.7); 3.760 (2.2); 3.743 (8.0); 3.730 (10.1); 3.716 (10.4); 3.703 (11.2); 3.690 (5.2); 3.679 (0.5); 3.536 (4.5); 3.522 (4.6); 3.516 (5.0); 3.509 (4.1); 3.502 (5.1); 3.496 (3.7); 3.489 (3.9); 3.475 (3.7); 2.148 (0.7); 2.133 (1.3); 2.112 (3.8); 2.098 (8.5); 2.092 (4.3); 2.084 (8.6); 2.078 (6.4); 2.072 (5.2); 2.062 (7.3); 2.049 (3.3); 2.038 (1.0); 2.027 (1.2); 2.013 (0.5); 1.576 (7.4); 0.008 (5.0); 0.0063 (1.8); 0.0055 (2.1); 0.000 (145.6); 0.005 (1.2); 0.006 (1.0); 0.007 (0.9); 0.009 (3.9)
[0413] Example 460 (erythro): .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =8.209 (15.4); 8.203 (15.2); 7.521 (0.6); 7.433 (8.3); 7.427 (8.2); 7.413 (10.9); 7.406 (10.5); 7.363 (0.5); 7.313 (0.6); 7.280 (18.3); 7.262 (95.6); 7.215 (1.3); 7.175 (4.7); 7.167 (5.4); 7.161 (5.3); 7.153 (8.6); 7.145 (5.3); 7.139 (4.9); 7.131 (4.7); 7.000 (2.1); 6.992 (2.2); 6.990 (2.6); 6.982 (4.0); 6.977 (4.9); 6.970 (6.1); 6.967 (5.5); 6.964 (3.8); 6.959 (7.9); 6.952 (5.5); 6.949 (5.7); 6.943 (8.8); 6.931 (7.3); 6.920 (9.3); 6.909 (9.0); 6.898 (3.8); 6.886 (3.3); 5.299 (0.7); 4.359 (15.1); 4.342 (16.0); 3.768 (3.8); 3.755 (9.3); 3.742 (10.0); 3.728 (13.8); 3.715 (10.1); 3.697 (3.1); 3.554 (4.5); 3.541 (5.0); 3.533 (5.3); 3.527 (4.7); 3.520 (5.5); 3.514 (4.4); 3.506 (4.2); 3.493 (3.9); 2.158 (0.7); 2.144 (1.5); 2.138 (1.0); 2.123 (4.0); 2.108 (6.7); 2.103 (6.9); 2.090 (10.1); 2.079 (6.4); 2.068 (7.0); 2.056 (4.4); 2.044 (1.9); 2.033 (2.0); 2.020 (1.1); 1.531 (10.9); 1.284 (0.5); 1.255 (1.1); 0.008 (1.7); 0.000 (34.5); 0.008 (1.8)
[0414] Example 460 (threo): .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =8.159 (13.6); 8.153 (13.8); 7.620 (9.8); 7.613 (9.6); 7.599 (11.3); 7.593 (11.0); 7.520 (1.0); 7.324 (0.6); 7.317 (16.0); 7.316 (15.9); 7.296 (13.9); 7.295 (14.1); 7.261 (186.4); 7.011 (2.7); 6.999 (3.2); 6.998 (2.1); 6.988 (8.3); 6.976 (8.4); 6.965 (6.7); 6.960 (5.0); 6.953 (10.5); 6.949 (5.8); 6.942 (9.2); 6.937 (2.7); 6.934 (5.1); 6.931 (6.1); 6.926 (2.3); 6.923 (5.1); 6.919 (3.7); 6.911 (2.4); 6.908 (1.8); 6.901 (2.0); 6.854 (4.4); 6.847 (4.1); 6.840 (4.6); 6.833 (8.0); 6.825 (4.2); 6.819 (4.6); 6.812 (3.7); 4.146 (14.6); 4.124 (16.0); 3.717 (3.6); 3.706 (4.3); 3.702 (4.4); 3.690 (6.7); 3.679 (5.3); 3.675 (5.2); 3.665 (4.7); 3.656 (2.9); 3.646 (2.9); 3.634 (2.9); 3.626 (4.8); 3.618 (3.2); 3.605 (2.8); 3.596 (2.7); 3.429 (4.4); 3.417 (5.0); 3.406 (5.3); 3.402 (4.6); 3.394 (5.3); 3.390 (4.9); 3.379 (4.2); 3.367 (4.0); 2.369 (1.8); 2.359 (1.9); 2.354 (2.0); 2.345 (3.4); 2.334 (3.5); 2.330 (2.4); 2.324 (3.0); 2.319 (3.5); 2.310 (4.8); 2.301 (2.8); 2.295 (2.6); 2.286 (2.4); 2.187 (1.5); 2.184 (1.6); 2.174 (2.9); 2.165 (1.7); 2.162 (1.9); 2.159 (1.8); 2.156 (1.8); 2.146 (3.3); 2.137 (2.9); 2.130 (1.4); 2.127 (1.4); 2.124 (1.4); 2.121 (1.3); 2.111 (2.0); 2.101 (1.1); 2.098 (1.1); 1.482 (5.6); 1.333 (0.8); 1.284 (1.1); 1.255 (2.6); 0.008 (2.1); 0.0064 (0.7); 0.0055 (0.7); 0.005 (0.9); 0.004 (1.2); 0.000 (70.8); 0.006 (1.1); 0.007 (1.0); 0.008 (2.3)
[0415] Example 2003: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =8.372 (11.9); 8.365 (11.9); 8.078 (12.4); 8.072 (12.6); 7.743 (8.5); 7.737 (8.5); 7.722 (9.7); 7.716 (9.6); 7.650 (9.3); 7.643 (9.1); 7.629 (10.7); 7.623 (10.3); 7.519 (5.1); 7.423 (13.1); 7.403 (11.6); 7.294 (16.1); 7.279 (1.9); 7.273 (16.0); 7.272 (16.7); 7.269 (6.2); 7.268 (6.6); 7.2674 (6.9); 7.2665 (8.1); 7.266 (10.0); 7.265 (12.2); 7.260 (902.5); 7.254 (6.6); 7.253 (5.5); 7.252 (4.3); 7.251 (3.4); 7.2503 (3.1); 7.2496 (2.8); 7.249 (2.2); 7.248 (2.1); 7.247 (2.0); 7.246 (2.0); 7.245 (1.7); 7.236 (1.1); 7.234 (1.0); 7.229 (1.9); 7.210 (2.0); 7.193 (2.4); 7.180 (2.5); 7.170 (6.4); 7.157 (5.4); 7.147 (5.6); 7.135 (5.4); 7.125 (2.3); 7.112 (2.4); 7.051 (2.5); 7.039 (2.6); 7.028 (6.4); 7.016 (6.4); 7.006 (6.5); 6.996 (6.3); 6.993 (6.6); 6.983 (2.7); 6.971 (2.7); 6.935 (2.4); 6.929 (2.6); 6.925 (2.6); 6.920 (2.7); 6.911 (4.3); 6.906 (4.4); 6.902 (4.2); 6.896 (4.0); 6.888 (2.2); 6.882 (2.2); 6.878 (2.1); 6.873 (1.9); 6.773 (2.3); 6.767 (2.5); 6.763 (2.5); 6.758 (2.5); 6.749 (4.0); 6.743 (4.5); 6.740 (4.4); 6.734 (4.0); 6.725 (2.2); 6.720 (2.3); 6.716 (2.2); 6.711 (2.1); 5.299 (2.4); 4.336 (12.0); 4.311 (13.4); 4.262 (13.5); 4.234 (16.0); 3.949 (2.6); 3.940 (2.7); 3.921 (4.8); 3.912 (4.9); 3.892 (2.4); 3.883 (2.4); 3.869 (2.2); 3.857 (2.5); 3.843 (3.8); 3.832 (4.0); 3.817 (2.1); 3.805 (2.1); 3.775 (3.0); 3.761 (3.9); 3.749 (5.6); 3.737 (4.7); 3.734 (4.7); 3.723 (3.9); 3.639 (2.6); 3.626 (3.6); 3.613 (5.4); 3.599 (4.6); 3.587 (3.5); 3.486 (3.3); 3.474 (3.7); 3.462 (4.1); 3.451 (4.1); 3.436 (3.1); 3.424 (3.2); 3.418 (3.0); 3.406 (3.1); 3.395 (3.4); 3.383 (3.5); 3.368 (2.6); 3.356 (2.4); 2.578 (1.6); 2.568 (1.7); 2.564 (1.9); 2.555 (3.0); 2.544 (3.4); 2.530 (3.4); 2.520 (4.0); 2.510 (2.4); 2.506 (2.2); 2.496 (1.9); 2.321 (1.4); 2.310 (2.8); 2.294 (1.7); 2.282 (3.1); 2.275 (2.9); 2.271 (2.5); 2.247 (2.1); 2.082 (1.8); 2.070 (1.4); 2.055 (2.5); 2.051 (2.2); 2.047 (2.9); 2.032 (1.7); 2.021 (2.3); 2.005 (1.2); 1.882 (1.5); 1.869 (2.4); 1.857 (2.4); 1.847 (3.6); 1.834 (3.4); 1.822 (1.9); 1.811 (1.8); 1.798 (1.3); 1.530 (6.4); 0.331 (0.8); 0.238 (0.6); 0.157 (1.1); 0.146 (1.0); 0.034 (0.6); 0.008 (10.4); 0.000 (351.7); 0.009 (9.7); 0.050 (0.6); 0.150 (1.1)
[0416] Example 2006: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =8.613 (10.9); 8.607 (10.9); 8.485 (10.6); 8.479 (10.8); 8.457 (13.4); 8.451 (13.3); 8.331 (1.2); 8.325 (1.2); 8.186 (10.2); 8.181 (10.3); 7.756 (6.3); 7.751 (11.5); 7.746 (5.9); 7.667 (7.1); 7.661 (12.7); 7.656 (6.7); 7.518 (9.1); 7.471 (1.0); 7.359 (0.8); 7.347 (0.7); 7.340 (0.7); 7.323 (0.7); 7.312 (0.8); 7.294 (2.1); 7.286 (2.2); 7.259 (1642.2); 7.253 (7.4); 7.252 (5.6); 7.251 (4.0); 7.2504 (3.1); 7.2496 (2.9); 7.249 (2.5); 7.248 (2.4); 7.247 (1.8); 7.2464 (2.1); 7.2456 (1.8); 7.245 (1.3); 7.244 (1.5); 7.243 (1.3); 7.2424 (1.4); 7.2416 (1.2); 7.241 (1.1); 7.240 (1.1); 7.239 (1.1); 7.238 (0.8); 7.237 (0.8); 7.235 (1.0); 7.227 (1.0); 7.218 (0.7); 7.215 (0.7); 7.210 (2.7); 7.209 (2.2); 7.200 (1.9); 7.187 (1.7); 7.177 (4.1); 7.171 (1.8); 7.164 (4.6); 7.154 (5.1); 7.146 (5.0); 7.142 (5.8); 7.131 (4.1); 7.119 (4.0); 7.055 (2.0); 7.042 (1.9); 7.032 (4.7); 7.019 (4.9); 7.009 (5.1); 6.996 (12.9); 6.986 (2.7); 6.974 (3.3); 6.961 (1.4); 6.950 (1.4); 6.942 (2.4); 6.936 (2.8); 6.932 (2.8); 927 (3.1); 6.918 (4.6); 6.913 (5.2); 6.909 (5.0); 6.903 (5.1); 6.895 (3.9); 6.889 (4.0); 6.885 (3.6); 6.880 (3.5); 6.812 (1.1); 6.783 (2.2); 6.774 (1.9); 6.768 (2.1); 6.760 (3.0); 6.754 (3.2); 6.750 (3.2); 6.745 (2.8); 6.736 (1.7); 6.731 (1.5); 6.721 (1.7); 6.708 (1.2); 6.696 (0.8); 6.667 (1.2); 5.298 (16.0); 4.392 (1.2); 4.382 (1.3); 4.341 (8.1); 4.316 (9.1); 4.259 (9.8); 4.231 (11.5); 4.113 (1.1); 3.951 (2.2); 3.940 (2.0); 3.922 (3.5); 3.913 (3.7); 3.895 (2.1); 3.883 (2.7); 3.870 (1.9); 3.855 (3.2); 3.844 (3.2); 3.829 (2.2); 3.817 (2.2); 3.781 (3.5); 3.767 (3.7); 3.754 (4.8); 3.742 (4.6); 3.728 (4.3); 3.697 (5.0); 3.682 (6.8); 3.666 (5.2); 3.643 (3.3); 3.631 (3.7); 3.617 (4.2); 3.603 (3.6); 3.591 (2.8); 3.494 (3.2); 3.481 (3.5); 3.469 (4.0); 3.458 (4.3); 3.442 (4.2); 3.430 (4.9); 3.417 (4.0); 3.406 (4.4); 3.379 (3.6); 3.368 (3.3); 3.285 (1.9); 3.246 (1.8); 3.216 (1.8); 3.124 (1.7); 3.039 (1.3); 2.976 (1.3); 2.899 (1.3); 2.824 (2.3); 2.806 (2.9); 2.786 (2.3); 2.624 (1.5); 2.573 (2.2); 2.563 (2.3); 2.549 (3.1); 2.539 (3.5); 2.524 (3.3); 2.514 (3.6); 2.505 (2.7); 2.491 (2.1); 2.324 (3.4); 2.295 (3.5); 2.261 (2.5); 2.169 (2.3); 2.094 (3.6); 2.067 (3.4); 2.059 (3.8); 2.045 (3.7); 2.033 (4.2); 1.903 (2.5); 1.887 (4.1); 1.877 (3.1); 1.866 (4.6); 1.855 (4.2); 1.841 (3.5); 1.833 (2.8); 1.819 (2.6); 1.807 (2.2); 1.583 (4.0); 1.333 (2.5); 1.256 (8.0); 1.217 (1.9); 1.202 (1.3); 1.085 (0.8); 0.880 (1.0); 0.146 (1.9); 0.125 (2.1); 0.035 (0.7); 0.015 (1.8); 0.008 (20.0); 0.000 (699.5); 0.009 (19.0); 0.033 (0.7); 0.051 (1.3); 0.114 (1.2); 0.150 (1.9)
[0417] Example 2001: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =8.556 (11.0); 8.552 (11.4); 8.544 (11.4); 8.540 (11.3); 8.504 (7.7); 8.500 (8.2); 8.492 (8.2); 8.488 (8.0); 8.418 (12.3); 8.412 (12.3); 8.380 (8.7); 8.375 (8.7); 7.642 (3.6); 7.637 (4.7); 7.632 (3.5); 7.622 (3.9); 7.617 (5.1); 7.612 (3.8); 7.520 (2.5); 7.458 (4.5); 7.453 (6.2); 7.448 (4.6); 7.438 (6.3); 7.434 (10.2); 7.416 (8.4); 7.411 (8.8); 7.397 (5.1); 7.393 (5.1); 7.374 (0.9); 7.295 (3.4); 7.291 (3.4); 7.282 (3.6); 7.277 (7.1); 7.275 (5.5); 7.272 (6.5); 7.270 (6.3); 7.261 (467.8); 7.252 (6.2); 7.247 (8.0); 7.242 (13.5); 7.239 (13.9); 7.234 (3.6); 7.229 (15.6); 7.225 (5.4); 7.222 (9.6); 7.220 (7.5); 7.216 (3.7); 7.213 (3.7); 7.208 (11.1); 7.204 (4.0); 7.200 (8.3); 7.196 (10.1); 7.191 (3.7); 7.181 (11.1); 7.178 (11.5); 7.162 (4.7); 7.159 (4.6); 7.133 (2.2); 7.129 (2.4); 7.114 (5.2); 7.110 (5.1); 7.096 (4.6); 7.091 (3.8); 7.073 (6.5); 7.070 (7.2); 7.055 (6.7); 7.052 (7.1); 7.036 (2.7); 7.033 (3.0); 7.014 (4.7); 7.011 (4.2); 6.997 (2.9); 6.993 (4.1); 6.990 (3.9); 6.987 (4.7); 6.984 (4.2); 6.966 (3.8); 6.963 (3.7); 6.955 (6.0); 6.952 (6.1); 6.935 (5.5); 6.932 (6.2); 6.930 (6.9); 6.926 (6.3); 6.909 (5.3); 6.906 (5.2); 5.298 (2.3); 4.330 (15.0); 4.312 (16.0); 4.166 (10.1); 4.145 (11.1); 3.769 (2.7); 3.751 (6.2); 3.732 (6.2); 3.715 (5.6); 3.702 (7.5); 3.688 (8.7); 3.675 (12.6); 3.668 (4.2); 3.662 (6.9); 3.652 (8.3); 3.642 (5.4); 3.636 (6.1); 3.625 (5.1); 3.615 (2.3); 3.525 (4.4); 3.508 (6.7); 3.498 (3.8); 3.491 (4.8); 3.481 (5.5); 3.464 (3.5); 3.430 (3.0); 3.417 (3.4); 3.408 (3.5); 3.403 (2.8); 3.394 (3.5); 3.390 (3.1); 3.381 (2.8); 3.368 (2.7); 2.381 (1.2); 2.371 (1.3); 2.365 (1.3); 2.358 (1.4); 2.356 (1.7); 2.346 (2.6); 2.336 (2.2); 2.331 (2.5); 2.324 (2.6); 2.321 (2.4); 2.314 (2.1); 2.308 (1.9); 2.298 (1.9); 2.265 (1.3); 2.262 (1.3); 2.251 (2.5); 2.241 (1.4); 2.237 (1.7); 2.223 (2.5); 2.212 (1.6); 2.209 (1.4); 2.202 (1.0); 2.188 (1.4); 2.175 (0.7); 2.133 (6.1); 2.120 (9.3); 2.115 (10.1); 2.100 (10.6); 2.084 (5.7); 1.583 (3.2); 1.255 (0.5); 0.069 (2.5); 0.008 (5.1); 0.000 (162.6); 0.009 (4.2)
[0418] Example 15 (threo): .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =8.109 (2.4); 8.001 (2.4); 7.934 (6.0); 7.928 (5.9); 7.915 (5.3); 7.909 (5.9); 7.805 (7.4); 7.518 (15.8); 7.321 (3.0); 7.292 (6.5); 7.259 (2865.7); 7.210 (8.9); 7.191 (6.8); 7.175 (3.1); 7.170 (3.5); 7.154 (2.3); 6.995 (16.0); 6.954 (3.7); 6.933 (2.3); 6.826 (7.3); 6.805 (11.3); 6.783 (6.3); 4.358 (2.4); 4.334 (3.0); 4.264 (8.9); 4.236 (10.4); 3.921 (2.7); 3.876 (3.4); 3.739 (3.1); 3.727 (3.7); 3.712 (3.1); 3.457 (3.2); 2.500 (2.8); 2.312 (2.3); 2.282 (2.3); 2.043 (2.5); 1.532 (919.9); 1.484 (2.6); 1.315 (4.6); 1.300 (6.8); 1.289 (4.8); 1.258 (3.6); 0.882 (2.3); 0.146 (3.6); 0.008 (40.0); 0.000 (1113.5); 0.009 (40.0); 0.050 (3.4); 0.149 (4.0)
[0419] Example 463: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =8.529 (15.9); 8.524 (16.0); 8.496 (9.9); 8.491 (9.9); 8.309 (14.4); 8.304 (14.6); 8.273 (8.4); 8.268 (8.6); 7.653 (5.7); 7.648 (9.7); 7.643 (5.0); 7.520 (1.1); 7.457 (7.5); 7.452 (13.8); 7.446 (7.2); 7.276 (0.5); 7.275 (0.6); 7.274 (0.6); 7.2723 (0.8); 7.2715 (0.8); 7.271 (1.0); 7.270 (1.1); 7.2683 (1.6); 7.2675 (1.7); 7.261 (204.4); 7.171 (3.3); 7.163 (3.6); 7.157 (3.6); 7.149 (6.5); 7.141 (3.7); 7.135 (3.5); 7.127 (3.5); 7.027 (1.6); 7.015 (1.9); 7.012 (2.2); 7.004 (5.2); 6.997 (2.1); 6.992 (5.1); 6.990 (5.0); 6.987 (2.4); 6.982 (5.3); 6.980 (6.9); 6.976 (2.7); 6.972 (7.2); 6.969 (6.4); 6.964 (4.5); 6.961 (6.3); 6.959 (3.4); 6.953 (4.1); 6.950 (6.6); 6.943 (3.0); 6.940 (3.8); 6.938 (6.1); 6.933 (3.1); 6.926 (7.7); 6.921 (1.9); 6.915 (7.2); 6.910 (1.6); 6.903 (2.7); 6.892 (2.5); 6.875 (2.2); 6.868 (2.0); 6.861 (2.3); 6.854 (4.0); 6.846 (2.0); 6.840 (2.3); 6.832 (1.8); 5.298 (5.4); 4.361 (12.1); 4.344 (12.7); 4.154 (7.5); 4.133 (8.2); 3.757 (3.8); 3.741 (5.4); 3.733 (4.9); 3.718 (5.7); 3.702 (2.8); 3.679 (1.6); 3.666 (2.3); 3.657 (1.6); 3.645 (1.5); 3.637 (2.6); 3.628 (1.6); 3.617 (1.5); 3.607 (1.4); 3.530 (2.2); 3.404 (1.5); 3.379 (0.8); 2.352 (0.9); 2.343 (1.0); 2.337 (1.0); 2.328 (1.6); 2.317 (1.8); 2.314 (1.2); 2.308 (1.6); 2.302 (1.8); 2.293 (2.4); 2.284 (1.5); 2.279 (1.4); 2.269 (1.3); 2.202 (0.8); 2.200 (0.8); 2.190 (1.6); 2.180 (0.9); 2.177 (1.0); 2.174 (0.9); 2.171 (1.0); 2.168 (1.2); 2.159 (1.8); 2.152 (1.5); 2.149 (1.1); 2.144 (1.4); 2.139 (1.1); 2.123 (3.3); 2.109 (6.1); 2.103 (3.5); 2.094 (6.7); 2.087 (4.7); 2.084 (3.9); 2.073 (6.0); 2.059 (2.6); 2.049 (0.7); 2.038 (0.9); 1.578 (3.9); 1.457 (3.1); 1.367 (1.7); 0.069 (0.5); 0.008 (2.3); 0.0063 (0.7); 0.0055 (0.7); 0.005 (0.9); 0.004 (1.2); 0.000 (81.5); 0.005 (1.6); 0.006 (1.3); 0.007 (1.1); 0.009 (2.6); 0.011 (0.5)
[0420] Example 1876: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =8.336 (9.4); 8.331 (9.1); 8.066 (9.8); 8.060 (10.0); 7.618 (5.0); 7.611 (4.3); 7.597 (11.1); 7.591 (11.7); 7.569 (14.1); 7.567 (14.2); 7.549 (5.8); 7.522 (6.2); 7.519 (11.8); 7.516 (6.1); 7.502 (10.0); 7.495 (10.2); 7.447 (14.2); 7.428 (8.0); 7.360 (1.7); 7.350 (1.5); 7.299 (1.8); 7.292 (2.3); 7.288 (2.4); 7.260 (1963.6); 7.210 (5.1); 7.012 (6.4); 7.005 (15.5); 6.996 (11.2); 6.984 (15.0); 6.977 (5.6); 6.850 (5.4); 6.844 (16.0); 6.823 (16.0); 6.816 (5.1); 4.278 (9.6); 4.253 (11.1); 4.204 (10.5); 4.176 (12.4); 3.992 (1.3); 3.892 (2.0); 3.883 (2.0); 3.865 (3.8); 3.854 (3.8); 3.837 (2.0); 3.827 (1.9); 3.812 (1.9); 3.800 (2.0); 3.785 (3.1); 3.774 (3.1); 3.759 (3.4); 3.748 (4.0); 3.732 (4.1); 3.720 (3.6); 3.706 (2.6); 3.635 (1.9); 3.623 (3.0); 3.609 (3.6); 3.595 (3.5); 3.583 (2.5); 3.470 (2.0); 3.458 (2.2); 3.445 (2.6); 3.435 (2.8); 3.419 (2.2); 3.409 (3.0); 3.386 (2.6); 3.375 (2.5); 3.361 (1.7); 3.349 (1.6); 2.547 (1.3); 2.532 (1.5); 2.522 (2.7); 2.512 (3.0); 2.498 (2.7); 2.488 (3.2); 2.479 (2.1); 2.464 (1.6); 2.264 (2.3); 2.236 (2.4); 2.201 (1.7); 2.052 (1.6); 2.017 (2.5); 2.005 (2.0); 1.991 (1.7); 1.869 (1.6); 1.856 (2.2); 1.845 (2.2); 1.834 (3.0); 1.821 (2.6); 1.799 (1.6); 1.536 (69.1); 1.284 (1.5); 0.157 (1.3); 0.146 (2.1); 0.008 (21.0); 0.000 (750.9); 0.009 (21.8); 0.050 (2.0); 0.150 (2.6)
[0421] Example 1836: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =8.537 (12.8); 8.531 (13.0); 8.498 (8.3); 8.492 (8.5); 8.298 (10.9); 8.293 (11.0); 8.268 (7.0); 8.263 (7.2); 7.654 (4.3); 7.649 (8.0); 7.643 (4.1); 7.519 (2.3); 7.448 (5.8); 7.443 (10.7); 7.438 (5.8); 7.309 (0.7); 7.292 (0.8); 7.269 (2.9); 7.260 (420.0); 7.254 (2.7); 7.253 (2.1); 7.252 (1.9); 7.2503 (1.1); 7.2495 (0.8); 7.249 (0.9); 7.248 (0.9); 7.247 (0.8); 7.2463 (0.7); 7.2455 (0.7); 7.244 (0.7); 7.242 (0.5); 7.232 (1.3); 7.227 (1.8); 7.214 (3.7); 7.210 (3.3); 7.205 (2.7); 7.196 (3.2); 7.191 (2.8); 7.184 (2.6); 7.172 (2.3); 7.163 (5.8); 7.154 (5.1); 7.152 (4.8); 7.149 (4.9); 7.146 (7.9); 7.137 (4.0); 7.131 (9.0); 7.125 (4.5); 7.117 (1.9); 7.113 (3.4); 7.108 (3.5); 7.105 (2.8); 7.101 (2.5); 7.093 (1.7); 7.087 (2.6); 7.081 (3.0); 7.076 (2.1); 7.073 (2.1); 7.070 (1.8); 7.064 (2.3); 7.058 (4.1); 7.054 (2.3); 7.050 (2.4); 7.041 (2.3); 7.038 (2.4); 7.033 (1.1); 7.030 (1.2); 7.017 (1.1); 6.996 (2.4); 6.928 (2.1); 6.913 (2.5); 6.909 (2.7); 6.900 (1.0); 6.895 (1.5); 5.299 (16.0); 4.370 (9.1); 4.353 (9.5); 4.162 (5.9); 4.141 (6.5); 3.804 (2.0); 3.788 (3.7); 3.783 (3.0); 3.771 (2.8); 3.766 (4.6); 3.749 (3.4); 3.731 (3.4); 3.721 (3.2); 3.710 (2.9); 3.701 (3.5); 3.693 (2.8); 3.681 (2.8); 3.672 (2.7); 3.531 (1.9); 3.425 (1.0); 3.400 (1.4); 3.175 (1.3); 2.891 (1.4); 2.889 (1.4); 2.364 (0.7); 2.355 (0.8); 2.350 (0.7); 2.340 (1.1); 2.330 (1.5); 2.320 (1.4); 2.315 (1.6); 2.306 (1.9); 2.296 (1.2); 2.291 (1.2); 2.282 (1.0); 2.238 (0.8); 2.228 (1.5); 2.215 (0.9); 2.200 (1.4); 2.174 (1.0); 2.170 (1.3); 2.164 (1.1); 2.153 (2.6); 2.143 (2.5); 2.139 (3.6); 2.132 (4.7); 2.118 (4.9); 2.109 (4.0); 2.096 (2.3); 2.074 (0.8); 1.555 (8.5); 1.387 (2.6); 1.294 (1.8); 0.008 (4.8); 0.000 (165.4); 0.009 (4.8)
[0422] Example 6 (erythro): .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =8.693 (12.8); 8.688 (13.6); 8.507 (12.5); 8.502 (13.3); 7.888 (8.5); 7.883 (15.5); 7.878 (9.2); 7.520 (0.7); 7.349 (2.4); 7.333 (4.5); 7.328 (4.3); 7.317 (3.3); 7.312 (8.7); 7.307 (4.1); 7.296 (4.5); 7.291 (5.8); 7.275 (3.8); 7.261 (105.8); 7.228 (1.2); 6.997 (1.1); 6.973 (9.8); 6.951 (16.0); 6.929 (8.8); 5.298 (7.5); 4.327 (11.1); 4.302 (12.3); 3.862 (2.3); 3.851 (2.5); 3.836 (4.1); 3.824 (4.3); 3.821 (4.6); 3.811 (2.5); 3.799 (2.4); 3.727 (1.0); 3.623 (2.7); 3.618 (2.2); 3.608 (3.8); 3.596 (5.8); 3.584 (4.5); 3.581 (4.7); 3.570 (3.6); 3.564 (1.7); 3.423 (2.9); 3.410 (3.3); 3.400 (3.8); 3.388 (3.8); 3.384 (3.4); 3.373 (2.8); 3.361 (2.5); 2.112 (1.2); 2.100 (2.0); 2.088 (1.8); 2.084 (1.9); 2.077 (2.5); 2.073 (2.8); 2.069 (2.8); 2.065 (3.2); 2.057 (2.1); 2.053 (2.4); 2.050 (2.3); 2.038 (2.5); 2.026 (1.5); 1.877 (1.7); 1.863 (2.5); 1.852 (2.5); 1.843 (3.6); 1.829 (3.4); 1.821 (2.1); 1.808 (2.0); 1.794 (1.4); 1.476 (1.5); 1.333 (1.2); 1.284 (1.2); 1.256 (1.3); 0.008 (1.7); 0.000 (38.0); 0.009 (2.2)
[0423] Example 472 (erythro): .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =7.898 (1.5); 7.860 (11.3); 7.855 (14.3); 7.852 (12.8); 7.791 (12.5); 7.785 (10.6); 7.771 (12.3); 7.765 (10.6); 7.581 (1.0); 7.575 (1.0); 7.561 (1.0); 7.555 (1.0); 7.519 (2.2); 7.310 (1.0); 7.291 (1.7); 7.275 (2.3); 7.271 (3.5); 7.269 (4.2); 7.260 (392.8); 7.247 (1.5); 7.246 (1.4); 7.189 (0.6); 7.181 (0.7); 7.174 (0.7); 7.167 (0.9); 7.159 (0.6); 7.145 (0.6); 7.034 (3.3); 7.022 (4.0); 7.011 (9.7); 6.999 (10.2); 6.988 (8.3); 6.982 (6.1); 6.975 (11.8); 6.972 (6.7); 6.964 (10.3); 6.960 (3.9); 6.957 (6.0); 6.953 (6.9); 6.946 (5.8); 6.942 (4.3); 6.937 (1.9); 6.934 (2.9); 6.931 (2.1); 6.924 (2.4); 6.915 (0.6); 6.904 (0.5); 6.870 (5.0); 6.863 (4.7); 6.856 (5.3); 6.849 (9.0); 6.842 (4.7); 6.835 (5.1); 6.828 (4.1); 5.299 (0.5); 4.387 (1.4); 4.371 (1.6); 4.157 (14.8); 4.135 (16.0); 3.796 (0.6); 3.783 (0.9); 3.770 (1.0); 3.756 (1.3); 3.737 (4.4); 3.727 (5.4); 3.723 (5.3); 3.711 (7.6); 3.700 (6.0); 3.696 (5.9); 3.686 (5.0); 3.652 (3.2); 3.643 (3.6); 3.629 (4.2); 3.623 (5.6); 3.615 (3.9); 3.602 (3.5); 3.593 (3.2); 3.569 (0.6); 3.561 (0.6); 3.554 (0.6); 3.548 (0.6); 3.542 (0.5); 3.534 (0.5); 3.440 (4.5); 3.428 (5.2); 3.416 (5.9); 3.414 (5.1); 3.405 (5.8); 3.402 (5.4); 3.390 (4.3); 3.378 (4.0); 2.370 (2.3); 2.361 (2.4); 2.356 (2.5); 2.346 (4.2); 2.336 (4.4); 2.326 (3.7); 2.321 (4.4); 2.312 (6.0); 2.302 (3.4); 2.297 (3.2); 2.288 (2.8); 2.189 (2.2); 2.180 (3.6); 2.170 (2.4); 2.167 (2.4); 2.163 (2.4); 2.153 (4.2); 2.142 (3.9); 2.126 (2.0); 2.117 (2.8); 2.106 (2.2); 2.091 (0.7); 2.083 (0.7); 1.510 (2.2); 1.333 (1.4); 1.284 (1.3); 1.256 (1.8); 0.008 (5.1); 0.000 (138.5); 0.008 (4.5)
[0424] Example 1963: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =8.417 (15.9); 8.411 (16.0); 8.369 (14.0); 8.362 (14.2); 8.247 (7.9); 8.243 (12.9); 8.239 (8.0); 8.203 (6.9); 8.199 (11.5); 8.196 (7.0); 7.520 (1.1); 7.451 (3.3); 7.447 (3.6); 7.433 (6.7); 7.428 (7.0); 7.414 (4.0); 7.410 (4.1); 7.378 (3.9); 7.372 (5.2); 7.366 (3.7); 7.356 (3.9); 7.350 (5.3); 7.344 (3.7); 7.312 (2.4); 7.307 (2.4); 7.298 (2.4); 7.293 (5.0); 7.291 (3.6); 7.289 (3.9); 7.287 (3.3); 7.280 (4.3); 7.278 (3.6); 7.275 (4.6); 7.273 (6.2); 7.268 (6.0); 7.261 (206.1); 7.255 (5.7); 7.248 (3.9); 7.244 (3.4); 7.242 (3.1); 7.236 (2.8); 7.233 (2.9); 7.231 (3.6); 7.228 (4.7); 7.224 (3.4); 7.216 (7.8); 7.214 (7.3); 7.210 (3.8); 7.198 (8.7); 7.195 (9.2); 7.179 (3.8); 7.176 (3.7); 7.166 (4.0); 7.161 (5.6); 7.155 (3.9); 7.144 (4.0); 7.139 (5.6); 7.132 (5.3); 7.127 (2.5); 7.113 (5.1); 7.108 (5.1); 7.096 (5.6); 7.087 (7.7); 7.085 (7.8); 7.070 (6.6); 7.067 (7.4); 7.051 (2.5); 7.048 (2.7); 7.031 (4.7); 7.028 (4.7); 7.011 (4.1); 7.008 (4.0); 7.004 (4.7); 7.002 (4.3); 6.997 (1.6); 6.983 (3.8); 6.981 (3.6); 6.965 (4.8); 6.962 (4.8); 6.944 (4.5); 6.941 (5.1); 6.939 (5.6); 6.935 (5.1); 6.918 (4.1); 6.915 (4.2); 4.399 (10.9); 4.382 (11.5); 4.212 (9.2); 4.190 (9.9); 3.787 (2.3); 3.769 (5.4); 3.750 (5.8); 3.733 (5.5); 3.719 (3.8); 3.706 (4.5); 3.693 (3.6); 3.676 (4.0); 3.667 (5.6); 3.654 (4.8); 3.648 (4.5); 3.639 (3.8); 3.626 (2.6); 3.616 (2.4); 3.548 (1.8); 3.532 (3.4); 3.515 (2.4); 3.505 (2.7); 3.489 (1.5); 3.431 (1.4); 3.418 (1.6); 3.407 (2.2); 3.395 (2.3); 3.383 (1.4); 3.369 (1.2); 2.380 (1.2); 2.370 (1.3); 2.365 (1.3); 2.355 (1.7); 2.346 (2.7); 2.336 (2.3); 2.330 (2.7); 2.322 (2.9); 2.313 (2.2); 2.307 (2.1); 2.298 (1.9); 2.265 (1.3); 2.262 (1.3); 2.252 (2.5); 2.241 (1.4); 2.238 (1.7); 2.233 (1.4); 2.223 (2.5); 2.217 (1.8); 2.213 (1.8); 2.210 (1.4); 2.202 (1.0); 2.188 (1.4); 2.178 (0.8); 2.175 (0.9); 2.155 (5.2); 2.141 (7.5); 2.137 (8.7); 2.123 (8.7); 2.106 (4.8); 2.004 (0.5); 1.597 (2.1); 1.465 (2.2); 1.373 (1.7); 0.008 (2.3); 0.000 (76.6); 0.009 (2.2)
[0425] Example 1833: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =8.197 (15.2); 8.191 (15.2); 8.156 (11.3); 8.149 (11.4); 7.617 (7.7); 7.610 (7.6); 7.596 (8.8); 7.589 (8.6); 7.519 (5.3); 7.421 (8.3); 7.415 (8.2); 7.401 (11.0); 7.394 (11.0); 7.315 (13.3); 7.295 (11.1); 7.294 (11.4); 7.291 (3.5); 7.287 (19.1); 7.286 (18.8); 7.276 (2.5); 7.275 (2.7); 7.273 (3.4); 7.267 (20.9); 7.265 (24.7); 7.260 (966.2); 7.230 (2.4); 7.227 (3.9); 7.213 (7.1); 7.209 (4.6); 7.205 (3.7); 7.195 (5.6); 7.172 (3.2); 7.160 (3.2); 7.150 (8.3); 7.142 (7.4); 7.139 (7.0); 7.134 (13.4); 7.125 (5.6); 7.119 (13.3); 7.113 (6.2); 7.105 (2.5); 7.101 (5.3); 7.096 (6.0); 7.090 (4.6); 7.087 (2.3); 7.081 (2.6); 7.076 (5.1); 7.071 (5.7); 7.066 (3.8); 7.061 (3.6); 7.058 (3.6); 7.053 (4.1); 7.047 (7.2); 7.042 (4.1); 7.039 (4.3); 7.029 (3.9); 7.026 (4.4); 7.018 (2.1); 7.005 (1.8); 6.996 (5.6); 6.904 (4.1); 6.893 (2.8); 6.889 (5.0); 6.885 (5.1); 6.875 (1.9); 6.870 (2.7); 4.362 (15.4); 4.346 (16.0); 4.153 (11.5); 4.131 (12.7); 3.799 (3.2); 3.783 (5.9); 3.777 (4.1); 3.767 (4.6); 3.761 (7.6); 3.745 (5.6); 3.718 (5.7); 3.709 (5.6); 3.696 (4.7); 3.689 (5.7); 3.680 (5.2); 3.668 (5.0); 3.658 (4.0); 3.518 (2.9); 3.393 (2.5); 2.381 (1.4); 2.372 (1.5); 2.367 (1.5); 2.358 (2.4); 2.347 (2.8); 2.337 (2.4); 2.332 (2.9); 2.323 (3.6); 2.314 (2.1); 2.309 (1.9); 2.299 (1.9); 2.224 (1.4); 2.212 (2.4); 2.184 (2.8); 2.173 (2.8); 2.158 (2.0); 2.151 (4.8); 2.137 (8.7); 2.131 (4.8); 2.124 (7.6); 2.116 (7.8); 2.102 (8.3); 2.090 (3.5); 2.068 (1.1); 1.546 (81.8); 1.359 (4.3); 1.273 (3.2); 0.146 (1.0); 0.008 (10.2); 0.000 (370.0); 0.009 (10.2); 0.150 (1.0)
[0426] Example 2004: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =8.354 (11.7); 8.348 (11.5); 8.061 (11.1); 8.055 (11.2); 7.641 (6.0); 7.634 (5.8); 7.620 (12.0); 7.613 (11.7); 7.577 (15.8); 7.557 (7.9); 7.546 (6.9); 7.540 (6.8); 7.525 (10.4); 7.519 (16.0); 7.448 (15.1); 7.427 (9.8); 7.355 (0.9); 7.295 (1.9); 7.260 (1050.3); 7.211 (2.2); 7.193 (2.5); 7.181 (2.6); 7.170 (5.7); 7.158 (5.4); 7.148 (5.4); 7.135 (5.5); 7.125 (2.4); 7.113 (2.2); 7.055 (2.1); 7.043 (2.1); 7.032 (5.5); 7.020 (5.5); 7.010 (5.7); 6.996 (9.3); 6.987 (2.4); 6.974 (2.0); 6.935 (2.4); 6.926 (3.2); 6.920 (2.7); 6.911 (4.1); 6.906 (4.4); 6.902 (4.5); 6.896 (4.1); 6.888 (2.3); 6.882 (2.5); 6.873 (2.0); 6.775 (2.2); 6.769 (2.3); 6.760 (2.3); 6.752 (3.5); 6.746 (4.2); 6.743 (4.1); 6.736 (3.7); 6.728 (2.2); 6.722 (2.4); 6.713 (1.9); 4.314 (12.0); 4.289 (13.1); 4.244 (11.8); 4.216 (14.0); 3.946 (2.4); 3.937 (2.5); 3.919 (4.7); 3.909 (4.7); 3.890 (2.1); 3.880 (2.3); 3.864 (2.5); 3.853 (2.7); 3.838 (4.2); 3.827 (4.4); 3.812 (2.3); 3.801 (2.2); 3.761 (2.9); 3.746 (3.6); 3.734 (3.5); 3.721 (2.2); 3.624 (3.0); 3.611 (3.7); 3.598 (3.6); 3.585 (2.5); 3.449 (3.1); 3.416 (2.4); 3.405 (2.3); 3.391 (3.0); 3.381 (3.1); 2.575 (1.4); 2.561 (2.0); 2.551 (2.9); 2.540 (3.5); 2.526 (2.9); 2.516 (3.5); 2.507 (2.0); 2.492 (2.0); 2.306 (2.6); 2.278 (2.9); 2.243 (1.9); 2.077 (2.0); 2.042 (2.7); 2.016 (2.1); 1.876 (1.6); 1.863 (2.5); 1.851 (2.8); 1.841 (4.0); 1.828 (3.5); 1.816 (2.0); 1.805 (2.0); 1.540 (60.1); 1.320 (2.5); 1.242 (2.3); 0.146 (1.5); 0.008 (15.3); 0.000 (387.3); 0.009 (11.3); 0.150 (1.3)
[0427] Example 460 (threo): .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =8.159 (12.2); 8.153 (12.3); 7.620 (8.2); 7.614 (8.0); 7.600 (9.4); 7.593 (9.2); 7.521 (0.6); 7.316 (14.0); 7.296 (12.2); 7.262 (87.8); 7.213 (0.8); 7.011 (2.4); 6.999 (2.9); 6.988 (7.0); 6.976 (7.1); 6.964 (6.0); 6.960 (4.2); 6.952 (8.9); 6.949 (4.9); 6.941 (7.3); 6.937 (2.6); 6.934 (4.5); 6.930 (5.2); 6.923 (4.3); 6.919 (3.2); 6.911 (2.3); 6.908 (1.8); 6.901 (1.8); 6.855 (3.8); 6.847 (3.6); 6.841 (4.1); 6.833 (6.8); 6.826 (3.7); 6.819 (4.0); 6.812 (3.3); 5.299 (16.0); 4.147 (12.4); 4.125 (13.6); 3.716 (3.1); 3.705 (3.8); 3.701 (3.8); 3.690 (5.9); 3.678 (4.7); 3.674 (4.6); 3.664 (4.2); 3.656 (2.9); 3.647 (2.9); 3.634 (2.8); 3.627 (4.5); 3.619 (3.1); 3.606 (2.7); 3.597 (2.6); 3.428 (3.7); 3.416 (4.2); 3.405 (4.6); 3.402 (4.0); 3.393 (4.7); 3.390 (4.3); 3.378 (3.7); 3.366 (3.5); 2.368 (1.5); 2.359 (1.7); 2.353 (1.7); 2.344 (2.9); 2.333 (3.1); 2.324 (2.7); 2.319 (3.2); 2.309 (4.2); 2.300 (2.6); 2.295 (2.4); 2.285 (2.1); 2.184 (1.5); 2.174 (2.7); 2.161 (1.8); 2.158 (1.7); 2.156 (1.7); 2.146 (3.1); 2.137 (2.6); 2.127 (1.4); 2.123 (1.4); 2.111 (2.0); 2.101 (1.1); 2.098 (1.1); 1.496 (6.0); 1.333 (0.5); 1.284 (0.7); 1.255 (1.3); 0.008 (1.2); 0.000 (33.9); 0.009 (1.3)
[0428] Example 460 (erythro): .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =8.207 (14.7); 8.201 (15.0); 7.520 (0.7); 7.432 (8.1); 7.426 (8.1); 7.412 (10.7); 7.405 (10.5); 7.362 (0.5); 7.311 (0.7); 7.279 (18.0); 7.262 (108.2); 7.229 (1.0); 7.211 (1.4); 7.174 (4.3); 7.167 (4.8); 7.161 (4.7); 7.153 (8.2); 7.145 (4.9); 7.139 (4.7); 7.131 (4.6); 7.000 (1.9); 6.992 (2.0); 6.990 (2.5); 6.982 (3.8); 6.977 (4.6); 6.970 (5.7); 6.967 (5.2); 6.964 (3.2); 6.959 (7.8); 6.952 (5.0); 6.949 (5.3); 6.943 (8.2); 6.931 (7.0); 6.920 (9.2); 6.909 (9.0); 6.897 (3.6); 6.886 (3.2); 5.299 (1.0); 4.357 (15.1); 4.340 (16.0); 3.768 (3.7); 3.755 (8.8); 3.741 (9.3); 3.735 (5.9); 3.728 (13.4); 3.715 (9.4); 3.696 (2.9); 3.553 (4.3); 3.541 (4.7); 3.533 (5.0); 3.527 (4.3); 3.520 (5.2); 3.514 (4.1); 3.506 (4.0); 3.493 (3.8); 2.158 (0.7); 2.143 (1.4); 2.122 (3.8); 2.108 (6.1); 2.102 (6.5); 2.089 (9.4); 2.079 (5.8); 2.068 (6.6); 2.055 (4.1); 2.044 (1.7); 2.032 (1.8); 2.020 (1.0); 1.500 (10.9); 1.255 (1.0); 0.008 (1.3); 0.000 (39.9); 0.008 (1.8)
[0429] Example 6 (threo): .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =8.696 (0.8); 8.691 (0.8); 8.522 (15.6); 8.517 (15.8); 8.510 (1.2); 8.505 (0.9); 8.208 (12.2); 8.203 (12.3); 7.884 (0.9); 7.788 (8.7); 7.783 (16.0); 7.777 (8.2); 7.520 (1.0); 7.313 (0.6); 7.295 (0.6); 7.293 (0.5); 7.275 (0.8); 7.261 (176.3); 7.206 (2.3); 7.190 (4.7); 7.185 (4.4); 7.174 (2.7); 7.169 (9.6); 7.164 (3.0); 7.153 (4.4); 7.148 (5.3); 7.132 (2.6); 6.997 (1.0); 6.974 (0.5); 952 (0.9); 6.808 (8.7); 6.786 (14.5); 6.764 (7.7); 5.299 (6.2); 4.329 (0.6); 4.304 (0.7); 4.243 (12.2); 4.215 (14.5); 3.921 (2.1); 3.912 (2.2); 3.893 (3.9); 3.883 (3.9); 3.865 (2.0); 3.855 (1.9); 3.750 (2.6); 3.739 (3.1); 3.735 (3.1); 3.723 (5.1); 3.712 (3.8); 3.708 (3.7); 3.697 (3.2); 3.619 (2.1); 3.567 (0.8); 3.488 (2.7); 3.476 (3.0); 3.465 (3.0); 3.461 (2.7); 3.453 (3.3); 3.449 (2.8); 3.438 (2.5); 3.426 (2.4); 2.558 (1.3); 2.548 (1.5); 2.543 (1.5); 2.534 (2.2); 2.524 (2.9); 2.514 (2.2); 2.509 (2.9); 2.500 (2.9); 2.491 (1.9); 2.486 (1.8); 2.476 (1.6); 2.340 (0.7); 2.337 (1.2); 2.333 (0.9); 2.325 (2.0); 2.317 (0.9); 2.313 (1.5); 2.309 (1.6); 2.296 (2.3); 2.291 (2.1); 2.285 (1.7); 2.279 (1.2); 2.274 (1.1); 2.262 (1.4); 2.251 (0.8); 1.516 (1.2); 1.333 (0.8); 1.284 (1.0); 1.256 (1.1); 0.008 (2.0); 0.000 (62.2); 0.009 (1.6)
[0430] Example 85: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =8.640 (4.8); 8.630 (5.0); 8.601 (5.8); 8.460 (5.6); 8.456 (5.9); 8.448 (5.8); 8.444 (5.6); 8.413 (0.6); 8.295 (7.5); 8.290 (7.5); 7.782 (5.2); 7.762 (5.6); 7.669 (3.7); 7.664 (5.1); 7.659 (3.6); 7.649 (4.1); 7.644 (5.4); 7.639 (3.7); 7.520 (2.8); 7.391 (5.0); 7.379 (5.1); 7.371 (4.7); 7.359 (4.5); 7.335 (2.1); 7.319 (4.3); 7.314 (4.0); 7.303 (2.9); 7.298 (8.9); 7.293 (2.9); 7.282 (5.0); 7.277 (6.4); 7.261 (510.7); 7.230 (5.5); 7.218 (5.3); 7.212 (4.9); 7.210 (5.7); 7.200 (4.7); 7.162 (2.2); 7.146 (4.6); 7.141 (4.5); 7.130 (2.8); 7.125 (9.3); 7.120 (3.0); 7.109 (4.4); 7.104 (5.1); 7.088 (2.5); 6.997 (2.8); 6.965 (9.9); 6.943 (16.0); 6.922 (8.7); 6.765 (7.9); 6.743 (13.2); 6.721 (7.0); 5.298 (4.8); 4.335 (8.9); 4.310 (9.8); 4.265 (10.6); 4.237 (12.4); 3.937 (2.1); 3.926 (2.5); 3.908 (3.9); 3.899 (4.0); 3.871 (3.2); 3.863 (2.1); 3.847 (3.3); 3.836 (3.3); 3.821 (1.9); 3.809 (1.7); 3.741 (2.7); 3.730 (3.2); 3.726 (3.3); 3.714 (5.7); 3.709 (4.7); 3.703 (4.0); 3.699 (3.8); 3.688 (3.4); 3.602 (2.9); 3.591 (2.3); 3.580 (2.9); 3.576 (3.1); 3.564 (5.3); 3.553 (3.8); 3.549 (3.8); 3.538 (3.0); 3.493 (2.9); 3.480 (3.2); 3.470 (3.4); 3.466 (2.9); 3.458 (3.5); 3.453 (2.9); 3.443 (2.6); 3.430 (2.6); 3.398 (2.8); 3.386 (3.0); 3.376 (3.4); 3.371 (2.9); 3.363 (3.4); 3.359 (2.8); 3.349 (2.4); 3.336 (2.1); 2.926 (0.7); 2.907 (0.5); 2.578 (1.3); 2.568 (1.4); 2.563 (1.4); 2.554 (2.0); 2.544 (2.7); 2.533 (2.2); 2.529 (2.7); 2.520 (2.6); 2.511 (1.9); 2.505 (1.7); 2.496 (1.6); 2.346 (1.3); 2.334 (1.8); 2.322 (1.6); 2.318 (1.7); 2.304 (2.4); 2.283 (1.3); 2.271 (1.3); 2.259 (0.9); 2.086 (1.6); 2.051 (2.5); 2.037 (1.7); 2.024 (1.9); 1.857 (1.6); 1.842 (2.1); 1.830 (2.3); 1.822 (3.0); 1.808 (2.9); 1.798 (1.8); 1.789 (1.8); 1.774 (1.4); 1.620 (3.9); 1.359 (0.5); 1.284 (0.7); 1.255 (2.8); 0.940 (0.5); 0.146 (0.5); 0.069 (6.4); 0.008 (5.8); 0.000 (181.4); 0.009 (5.2); 0.150 (0.5)
[0431] Example 1: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =8.190 (8.6); 8.183 (8.7); 7.875 (4.3); 7.868 (4.1); 7.856 (4.7); 7.853 (5.2); 7.850 (4.8); 7.847 (4.8); 7.835 (4.5); 7.829 (4.3); 7.519 (1.4); 7.340 (2.4); 7.324 (4.9); 7.319 (4.1); 7.308 (2.9); 7.303 (10.0); 7.298 (3.2); 7.287 (4.2); 7.282 (5.8); 7.266 (5.6); 7.260 (243.5); 7.147 (0.6); 7.020 (6.4); 7.012 (6.4); 6.998 (6.3); 6.991 (6.1); 6.969 (4.7); 6.965 (9.9); 6.948 (4.9); 6.943 (16.0); 6.939 (5.2); 6.922 (8.5); 6.918 (4.2); 4.356 (11.4); 4.331 (12.5); 3.857 (2.0); 3.846 (2.2); 3.831 (3.5); 3.820 (3.5); 3.805 (2.0); 3.794 (1.9); 3.621 (2.3); 3.610 (2.9); 3.607 (3.0); 3.595 (5.0); 3.583 (3.7); 3.580 (3.8); 3.568 (3.0); 3.416 (2.5); 3.404 (2.8); 3.393 (3.1); 3.381 (3.1); 3.366 (2.2); 3.354 (2.0); 2.104 (0.9); 2.092 (1.7); 2.080 (1.4); 2.077 (1.5); 2.073 (1.3); 2.069 (2.1); 2.065 (2.3); 2.061 (2.3); 2.058 (2.7); 2.054 (2.1); 2.050 (1.3); 2.046 (1.9); 2.042 (1.8); 2.031 (2.1); 2.019 (1.1); 1.878 (1.6); 1.865 (2.0); 1.853 (2.1); 1.843 (3.2); 1.829 (3.0); 1.820 (1.5); 1.808 (1.5); 1.795 (1.1); 1.538 (2.4); 1.333 (1.0); 1.284 (1.4); 1.255 (1.8); 0.008 (2.6); 0.000 (85.5); 0.009 (2.4)
[0432] Example 462: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =8.436 (11.9); 8.429 (11.6); 8.403 (7.7); 8.397 (7.4); 8.277 (7.1); 8.273 (10.2); 8.227 (6.6); 7.520 (0.6); 7.410 (2.4); 7.405 (3.2); 7.399 (2.2); 7.389 (2.4); 7.383 (3.1); 7.377 (2.1); 7.262 (98.6); 7.221 (4.0); 7.215 (5.2); 7.210 (4.0); 7.199 (4.1); 7.193 (5.2); 7.188 (3.7); 7.178 (3.5); 7.170 (3.9); 7.164 (3.8); 7.156 (5.9); 7.148 (3.8); 7.142 (3.5); 7.134 (3.4); 7.113 (0.8); 7.018 (1.8); 7.006 (3.2); 6.995 (5.6); 6.987 (4.2); 6.983 (6.8); 6.976 (5.0); 6.972 (6.0); 6.965 (6.3); 6.961 (5.4); 6.957 (4.8); 6.954 (5.5); 6.951 (3.7); 6.947 (4.2); 6.942 (6.3); 6.935 (3.7); 6.930 (6.0); 6.925 (3.6); 6.918 (6.8); 6.912 (2.8); 6.907 (6.4); 6.895 (3.1); 6.884 (2.7); 6.870 (2.6); 6.863 (2.4); 6.856 (2.6); 6.849 (3.8); 6.841 (2.3); 6.835 (2.4); 6.828 (1.9); 5.298 (16.0); 4.408 (8.5); 4.391 (8.8); 4.368 (0.7); 4.364 (0.6); 4.355 (0.6); 4.351 (0.6); 4.196 (5.2); 4.175 (5.5); 3.771 (3.7); 3.758 (8.4); 3.745 (7.5); 3.731 (7.6); 3.719 (6.2); 3.709 (2.7); 3.704 (2.6); 3.693 (3.5); 3.681 (3.7); 3.677 (3.8); 3.667 (3.5); 3.657 (2.0); 3.648 (2.7); 3.641 (1.9); 3.628 (1.7); 3.619 (1.6); 3.560 (3.2); 3.547 (3.5); 3.540 (3.7); 3.533 (3.2); 3.527 (3.7); 3.520 (2.9); 3.513 (2.9); 3.500 (2.6); 3.434 (2.1); 3.422 (2.3); 3.410 (2.6); 3.407 (2.2); 3.398 (2.5); 3.395 (2.2); 3.384 (2.0); 3.372 (1.8); 2.365 (0.8); 2.356 (1.0); 2.350 (1.0); 2.341 (1.5); 2.330 (1.7); 2.320 (1.5); 2.315 (1.7); 2.306 (2.2); 2.297 (1.4); 2.292 (1.3); 2.282 (1.1); 2.204 (1.0); 2.195 (1.6); 2.179 (1.2); 2.165 (2.1); 2.157 (1.7); 2.150 (1.7); 2.129 (3.6); 2.114 (5.8); 2.109 (3.9); 2.100 (6.5); 2.094 (4.8); 2.079 (5.5); 2.065 (2.8); 2.056 (1.2); 2.042 (1.3); 2.031 (0.8); 2.004 (0.6); 1.602 (2.7); 0.008 (2.5); 0.000 (39.1); 0.009 (1.5)
[0433] Example 1835: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =8.443 (15.9); 8.436 (16.0); 8.404 (11.2); 8.397 (11.2); 8.267 (7.9); 8.263 (12.4); 8.259 (7.7); 8.224 (5.5); 8.220 (8.8); 8.216 (5.4); 7.520 (1.8); 7.410 (2.9); 7.404 (4.1); 7.398 (2.9); 7.388 (3.0); 7.382 (4.1); 7.376 (2.8); 7.290 (0.6); 7.287 (0.5); 7.285 (0.6); 7.282 (0.6); 7.280 (0.6); 7.279 (0.7); 7.2783 (0.7); 7.2775 (0.7); 7.277 (0.9); 7.276 (1.0); 7.275 (1.1); 7.2743 (1.2); 7.2735 (1.3); 7.273 (1.4); 7.272 (1.5); 7.271 (1.8); 7.2703 (2.0); 7.2695 (2.3); 7.269 (2.6); 7.268 (2.8); 7.267 (3.4); 7.2663 (4.1); 7.2655 (5.1); 7.265 (6.5); 7.261 (316.4); 7.256 (3.6); 7.255 (2.6); 7.254 (2.7); 7.2533 (1.5); 7.2525 (1.1); 7.252 (1.7); 7.251 (0.9); 7.250 (0.7); 7.2493 (0.8); 7.2485 (0.8); 7.248 (0.8); 7.247 (0.8); 7.246 (0.8); 7.243 (1.8); 7.239 (2.5); 7.233 (1.8); 7.225 (5.0); 7.220 (4.0); 7.216 (3.1); 7.206 (8.0); 7.201 (7.9); 7.195 (4.0); 7.184 (4.1); 7.178 (7.3); 7.173 (4.1); 7.168 (2.6); 7.165 (2.2); 7.160 (5.7); 7.158 (5.5); 7.147 (9.0); 7.144 (5.4); 7.140 (9.7); 7.129 (5.2); 7.124 (7.0); 7.118 (5.0); 7.112 (1.9); 7.109 (2.2); 7.105 (4.2); 7.100 (4.0); 7.096 (3.3); 7.092 (3.7); 7.088 (1.7); 7.085 (2.1); 7.078 (3.2); 7.073 (4.0); 7.067 (2.9); 7.064 (2.8); 7.061 (2.5); 7.055 (3.1); 7.049 (5.7); 7.046 (3.2); 7.042 (3.2); 7.032 (3.0); 7.030 (3.2); 7.025 (1.4); 7.021 (1.5); 7.011 (1.2); 7.009 (1.4); 6.997 (1.9); 6.931 (1.7); 6.927 (2.9); 6.923 (1.8); 6.916 (1.9); 6.912 (3.3); 6.908 (3.6); 6.898 (1.3); 6.893 (2.0); 6.889 (1.2); 5.299 (6.1); 4.418 (10.5); 4.401 (11.1); 4.201 (7.1); 4.179 (7.8); 3.824 (2.4); 3.807 (4.7); 3.802 (3.0); 3.791 (2.8); 3.786 (4.9); 3.769 (3.2); 3.759 (2.1); 3.744 (4.0); 3.734 (4.4); 3.723 (4.2); 3.714 (4.6); 3.706 (3.6); 3.694 (3.4); 3.685 (3.4); 3.534 (2.2); 3.422 (1.2); 3.410 (1.6); 3.397 (1.9); 3.386 (1.5); 3.373 (1.1); 2.378 (0.9); 2.369 (1.0); 2.363 (1.0); 2.354 (1.5); 2.343 (2.0); 2.334 (1.7); 2.329 (2.0); 2.319 (2.5); 2.310 (1.7); 2.305 (1.6); 2.295 (1.4); 2.241 (1.0); 2.231 (1.8); 2.218 (1.1); 2.203 (1.9); 2.196 (1.7); 2.181 (1.3); 2.167 (1.7); 2.160 (3.0); 2.146 (4.5); 2.139 (5.7); 2.126 (6.0); 2.116 (4.9); 2.103 (2.7); 2.094 (0.6); 2.080 (0.7); 1.568 (10.7); 1.427 (3.9); 1.333 (2.6); 0.008 (3.8); 0.0063 (1.2); 0.0055 (1.3); 0.005 (1.6); 0.000 (122.7); 0.005 (2.1); 0.006 (1.6); 0.007 (1.4); 0.009 (3.7)
[0434] Example 543: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =8.573 (10.8); 8.569 (11.2); 8.561 (11.2); 8.557 (10.8); 8.535 (0.5); 8.531 (0.6); 8.523 (0.6); 8.519 (0.5); 8.449 (12.5); 8.444 (12.2); 8.405 (0.5); 8.399 (0.6); 7.520 (2.4); 7.493 (4.7); 7.488 (6.3); 7.483 (4.6); 7.473 (5.7); 7.468 (7.4); 7.463 (5.2); 7.345 (0.7); 7.293 (1.0); 7.261 (436.3); 7.255 (2.7); 7.252 (8.1); 7.250 (7.7); 7.244 (6.5); 7.242 (6.4); 7.232 (6.2); 7.230 (5.8); 7.159 (4.4); 7.151 (4.9); 7.145 (4.7); 7.137 (8.4); 7.129 (4.9); 7.123 (4.6); 7.116 (4.6); 6.997 (2.6); 6.987 (2.5); 6.979 (2.5); 6.977 (3.1); 6.969 (4.6); 6.964 (5.6); 6.961 (2.9); 6.957 (6.0); 6.954 (5.6); 6.951 (3.3); 6.946 (9.2); 6.939 (5.9); 6.936 (5.5); 6.928 (10.3); 6.916 (7.0); 6.904 (9.7); 6.893 (9.4); 6.882 (3.5); 6.870 (3.2); 5.299 (2.3); 4.334 (15.1); 4.316 (16.0); 4.148 (0.6); 4.127 (0.7); 3.760 (2.2); 3.743 (8.0); 3.730 (10.1); 3.716 (10.4); 3.703 (11.2); 3.690 (5.2); 3.679 (0.5); 3.536 (4.5); 3.522 (4.6); 3.516 (5.0); 3.509 (4.1); 3.502 (5.1); 3.496 (3.7); 3.489 (3.9); 3.475 (3.7); 2.148 (0.7); 2.133 (1.3); 2.112 (3.8); 2.098 (8.5); 2.092 (4.3); 2.084 (8.6); 2.078 (6.4); 2.072 (5.2); 2.062 (7.3); 2.049 (3.3); 2.038 (1.0); 2.027 (1.2); 2.013 (0.5); 1.576 (7.4); 0.008 (5.0); 0.0063 (1.8); 0.0055 (2.1); 0.000 (145.6); 0.005 (1.2); 0.006 (1.0); 0.007 (0.9); 0.009 (3.9)
[0435] Example 461: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =8.192 (7.3); 8.185 (7.4); 8.143 (4.9); 8.137 (5.0); 7.518 (2.7); 7.512 (2.4); 7.498 (6.5); 7.491 (6.7); 7.471 (8.2); 7.470 (8.4); 7.451 (3.3); 7.449 (3.1); 7.437 (6.9); 7.417 (9.8); 7.328 (6.8); 7.321 (6.7); 7.307 (4.6); 7.301 (4.5); 7.261 (174.5); 7.172 (2.5); 7.165 (2.8); 7.158 (2.7); 7.151 (4.7); 7.143 (2.7); 7.137 (2.6); 7.129 (2.6); 7.014 (1.2); 7.002 (2.6); 6.997 (1.4); 6.994 (1.5); 6.991 (4.6); 6.984 (2.7); 6.979 (6.5); 6.972 (3.7); 6.968 (4.8); 6.961 (6.1); 6.955 (5.8); 6.951 (4.8); 6.948 (5.0); 6.944 (5.4); 6.937 (6.1); 6.934 (3.5); 6.926 (6.8); 6.922 (2.2); 6.914 (6.2); 6.903 (2.3); 6.891 (1.7); 6.855 (1.9); 6.848 (1.8); 6.841 (2.0); 6.834 (3.4); 6.826 (1.9); 6.820 (2.0); 6.813 (1.6); 5.299 (16.0); 4.334 (9.0); 4.318 (9.5); 4.127 (6.5); 4.105 (7.0); 3.749 (2.6); 3.730 (4.2); 3.710 (4.1); 3.692 (2.4); 3.676 (1.4); 3.653 (1.3); 3.643 (1.3); 3.631 (1.2); 3.623 (2.1); 3.615 (1.3); 3.603 (1.2); 3.593 (1.1); 3.526 (1.7); 3.396 (1.3); 2.362 (0.8); 2.352 (0.9); 2.347 (0.9); 2.338 (1.4); 2.327 (1.5); 2.318 (1.3); 2.312 (1.5); 2.303 (2.1); 2.294 (1.2); 2.289 (1.1); 2.279 (1.0); 2.181 (0.7); 2.170 (1.3); 2.161 (0.8); 2.158 (0.9); 2.153 (1.1); 2.139 (1.8); 2.133 (1.6); 2.124 (1.1); 2.118 (2.6); 2.104 (3.8); 2.098 (3.8); 2.085 (4.8); 2.075 (2.9); 2.069 (2.3); 2.064 (3.4); 2.051 (2.0); 2.040 (0.6); 2.029 (0.8); 1.570 (8.4); 1.423 (2.5); 1.338 (1.5); 0.069 (0.6); 0.008 (1.9); 0.000 (64.2); 0.009 (1.8)
[0436] Example 1875: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =8.355 (10.2); 8.349 (10.1); 8.083 (10.3); 8.077 (10.3); 7.721 (7.6); 7.714 (7.4); 7.700 (8.3); 7.693 (8.3); 7.626 (7.4); 7.619 (7.3); 7.605 (8.4); 7.598 (8.3); 7.519 (5.6); 7.415 (11.3); 7.395 (9.8); 7.394 (9.7); 7.360 (1.2); 7.310 (1.5); 7.300 (1.2); 7.293 (13.7); 7.272 (14.5); 7.260 (1016.6); 7.229 (1.4); 7.225 (0.9); 7.012 (6.0); 7.005 (15.5); 6.996 (6.3); 6.984 (15.3); 6.977 (5.7); 6.847 (5.3); 6.841 (16.0); 6.820 (15.6); 6.813 (5.1); 4.299 (9.9); 4.274 (10.9); 4.222 (10.6); 4.194 (12.6); 3.896 (2.2); 3.886 (2.3); 3.868 (3.7); 3.858 (3.8); 3.840 (1.9); 3.830 (1.8); 3.817 (2.0); 3.805 (2.1); 3.791 (3.1); 3.779 (3.4); 3.750 (3.0); 3.734 (3.0); 3.722 (2.9); 3.708 (2.0); 3.637 (1.4); 3.624 (2.5); 3.611 (2.9); 3.597 (3.2); 3.585 (1.8); 3.436 (2.5); 3.412 (2.5); 3.389 (2.4); 2.550 (1.4); 2.536 (1.5); 2.526 (2.6); 2.516 (2.8); 2.502 (2.8); 2.491 (3.2); 2.482 (1.9); 2.468 (1.5); 2.268 (2.1); 2.240 (2.4); 2.204 (1.5); 2.057 (1.3); 2.030 (2.1); 2.022 (2.7); 2.007 (1.7); 1.995 (1.9); 1.874 (1.3); 1.861 (2.1); 1.849 (2.2); 1.839 (3.0); 1.826 (2.7); 1.815 (1.6); 1.804 (1.7); 1.791 (1.0); 1.538 (43.6); 1.303 (2.0); 1.227 (1.9); 0.331 (0.6); 0.157 (0.9); 0.146 (1.1); 0.008 (11.7); 0.000 (373.7); 0.009 (11.1); 0.031 (0.9); 0.150 (1.3)
[0437] Example 1962: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =8.153 (14.5); 8.146 (14.2); 8.112 (10.6); 8.105 (10.5); 7.519 (9.0); 7.487 (5.3); 7.481 (5.1); 7.466 (12.1); 7.460 (12.1); 7.435 (20.5); 7.434 (20.2); 7.420 (8.7); 7.415 (15.1); 7.412 (18.5); 7.402 (5.3); 7.397 (5.8); 7.390 (17.7); 7.309 (3.7); 7.304 (3.4); 7.295 (3.8); 7.290 (7.6); 7.285 (6.9); 7.281 (13.4); 7.274 (17.4); 7.270 (17.0); 7.268 (15.2); 7.267 (15.5); 7.260 (1631.1); 7.254 (24.8); 7.253 (21.9); 7.251 (9.2); 7.250 (8.8); 7.249 (8.0); 7.248 (7.0); 7.247 (8.2); 7.245 (5.0); 7.244 (7.0); 7.2404 (2.2); 7.2396 (2.1); 7.236 (3.8); 7.233 (5.0); 7.227 (5.4); 7.222 (3.2); 7.213 (3.6); 7.209 (9.1); 7.206 (8.5); 7.190 (11.2); 7.187 (11.5); 7.171 (4.4); 7.168 (4.1); 7.109 (2.0); 7.095 (6.6); 7.089 (9.4); 7.083 (12.9); 7.082 (12.6); 7.072 (8.1); 7.070 (8.3); 7.050 (1.9); 7.028 (5.1); 7.005 (4.6); 7.000 (6.6); 6.996 (9.8); 6.980 (4.5); 6.974 (6.4); 6.971 (6.3); 6.954 (5.5); 6.948 (7.4); 6.945 (6.4); 6.928 (5.2); 6.925 (5.5); 5.299 (3.8); 4.320 (15.3); 4.303 (16.0); 4.142 (12.0); 4.120 (13.1); 3.762 (2.8); 3.744 (9.8); 3.731 (8.8); 3.725 (7.2); 3.717 (8.9); 3.704 (10.9); 3.691 (6.1); 3.682 (3.5); 3.678 (3.5); 3.666 (5.8); 3.656 (4.1); 3.651 (4.2); 3.646 (3.3); 3.640 (4.2); 3.623 (2.8); 3.617 (3.7); 3.608 (3.2); 3.595 (2.8); 3.585 (2.6); 3.543 (4.1); 3.526 (7.2); 3.516 (3.8); 3.509 (4.5); 3.499 (5.9); 3.482 (3.5); 3.427 (3.2); 3.415 (3.6); 3.404 (3.8); 3.401 (3.3); 3.392 (3.9); 3.377 (3.0); 3.365 (2.9); 2.380 (1.2); 2.371 (1.7); 2.356 (2.2); 2.346 (2.8); 2.336 (2.5); 2.331 (3.2); 2.323 (3.2); 2.313 (2.2); 2.308 (2.3); 2.298 (1.9); 2.241 (1.4); 2.230 (2.5); 2.202 (2.7); 2.167 (1.8); 2.143 (6.4); 2.126 (11.0); 2.112 (10.3); 2.095 (5.9); 2.005 (1.2); 1.525 (10.9); 0.331 (1.2); 0.157 (2.0); 0.146 (1.9); 0.032 (1.1); 0.008 (19.4); 0.006 (7.3); 0.005 (8.7); 0.000 (635.3); 0.009 (16.8); 0.150 (2.0)
[0438] Example 15 (erythro): .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =8.110 (8.3); 8.107 (9.0); 8.104 (9.8); 8.101 (9.2); 8.021 (8.8); 8.015 (8.2); 8.001 (8.7); 7.995 (8.1); 7.934 (2.0); 7.928 (2.2); 7.915 (2.2); 7.909 (2.5); 7.806 (2.6); 7.518 (7.9); 7.355 (2.2); 7.339 (4.7); 7.335 (4.2); 7.323 (3.1); 7.318 (9.4); 7.313 (3.5); 7.309 (2.0); 7.303 (4.2); 7.297 (5.8); 7.292 (2.3); 7.281 (4.9); 7.260 (1475.3); 7.224 (1.5); 7.210 (1.9); 7.191 (2.7); 7.175 (1.3); 7.169 (1.8); 6.996 (8.3); 6.976 (9.7); 6.955 (16.0); 6.933 (8.5); 6.827 (2.4); 6.805 (4.3); 6.783 (2.1); 4.359 (11.5); 4.334 (12.9); 4.264 (3.5); 4.236 (3.8); 4.130 (2.0); 4.113 (1.8); 4.032 (1.4); 3.914 (1.0); 3.887 (1.2); 3.853 (2.3); 3.841 (2.3); 3.827 (3.6); 3.816 (3.4); 3.802 (2.1); 3.789 (2.0); 3.738 (1.3); 3.727 (1.4); 3.713 (1.1); 3.658 (1.4); 3.647 (2.8); 3.632 (4.3); 3.620 (4.7); 3.606 (3.8); 3.594 (1.7); 3.437 (2.9); 3.425 (3.1); 3.414 (3.4); 3.399 (2.6); 3.387 (2.5); 3.375 (1.3); 2.524 (1.1); 2.107 (1.7); 2.072 (2.8); 2.044 (9.4); 1.903 (1.4); 1.889 (2.3); 1.879 (2.2); 1.868 (3.2); 1.855 (2.7); 1.844 (1.4); 1.834 (1.6); 1.820 (1.2); 1.535 (512.6); 1.319 (2.0); 1.305 (3.0); 1.293 (2.2); 1.276 (3.7); 1.268 (8.1); 1.256 (11.7); 1.244 (6.3); 1.241 (3.5); 0.899 (1.5); 0.882 (4.7); 0.864 (1.7); 0.146 (1.7); 0.008 (17.0); 0.000 (580.3); 0.009 (17.1); 0.150 (1.6)
[0439] Example 1964: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =8.515 (15.7); 8.509 (16.0); 8.466 (10.8); 8.461 (10.9); 8.277 (13.9); 8.272 (14.1); 8.245 (9.2); 8.240 (9.5); 7.623 (5.7); 7.617 (10.6); 7.612 (5.6); 7.519 (3.3); 7.442 (3.3); 7.438 (3.6); 7.424 (6.5); 7.419 (7.0); 7.406 (10.5); 7.401 (17.0); 7.396 (7.2); 7.360 (0.6); 7.320 (2.4); 7.315 (2.5); 7.307 (2.9); 7.302 (5.3); 7.299 (3.8); 7.297 (4.1); 7.295 (3.6); 7.288 (5.0); 7.286 (4.0); 7.283 (4.8); 7.281 (6.3); 7.276 (6.4); 7.271 (4.5); 7.268 (8.4); 7.260 (614.4); 7.252 (2.9); 7.251 (3.5); 7.249 (2.3); 7.248 (2.0); 7.246 (2.9); 7.244 (1.7); 7.242 (2.7); 7.240 (3.2); 7.238 (3.4); 7.236 (3.0); 7.233 (3.1); 7.227 (2.5); 7.226 (3.6); 7.223 (6.8); 7.219 (8.9); 7.209 (1.8); 7.204 (9.2); 7.201 (9.5); 7.185 (4.1); 7.182 (4.0); 7.170 (0.6); 7.148 (0.6); 7.135 (1.4); 7.130 (1.7); 7.116 (4.2); 7.111 (3.9); 7.098 (5.4); 7.093 (8.5); 7.079 (5.4); 7.076 (6.0); 7.060 (2.1); 7.057 (2.2); 7.042 (3.7); 7.039 (3.3); 7.021 (3.1); 7.018 (3.1); 7.014 (3.6); 6.996 (4.3); 6.991 (2.8); 6.975 (4.7); 6.972 (4.8); 6.955 (4.5); 6.951 (4.9); 6.949 (5.4); 6.946 (5.0); 6.929 (4.3); 6.925 (4.2); 4.350 (12.3); 4.333 (13.0); 4.170 (8.3); 4.148 (9.0); 3.782 (0.6); 3.770 (2.3); 3.751 (6.2); 3.734 (7.2); 3.722 (3.4); 3.714 (3.9); 3.710 (3.8); 3.697 (2.7); 3.672 (2.2); 3.662 (3.5); 3.653 (3.3); 3.641 (2.6); 3.634 (3.0); 3.624 (2.3); 3.613 (2.1); 3.603 (2.0); 3.558 (1.5); 3.553 (1.5); 3.536 (2.7); 3.510 (2.3); 3.493 (1.3); 3.407 (1.7); 2.371 (0.9); 2.361 (1.0); 2.356 (1.0); 2.346 (1.3); 2.336 (2.1); 2.326 (1.8); 2.321 (2.1); 2.313 (2.2); 2.304 (1.8); 2.298 (1.8); 2.288 (1.6); 2.260 (1.1); 2.250 (2.1); 2.237 (1.4); 2.222 (2.1); 2.212 (1.5); 2.201 (0.9); 2.187 (1.2); 2.174 (0.7); 2.151 (5.1); 2.137 (7.5); 2.133 (8.5); 2.119 (8.7); 2.102 (4.9); 1.557 (5.2); 1.352 (2.4); 1.262 (1.8); 0.146 (0.7); 0.008 (6.9); 0.000 (249.9); 0.009 (7.0); 0.033 (0.6); 0.150 (0.8)
[0440] Example 14 (erythro): .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =8.068 (8.4); 8.065 (9.4); 8.063 (9.9); 8.060 (8.8); 7.878 (8.7); 7.872 (8.3); 7.858 (8.9); 7.852 (8.3); 7.519 (1.2); 7.355 (2.3); 7.339 (4.6); 7.334 (3.9); 7.323 (2.7); 7.318 (9.4); 7.313 (3.0); 7.302 (3.9); 7.297 (5.3); 7.281 (2.9); 7.275 (0.7); 7.273 (0.9); 7.270 (1.3); 7.269 (1.6); 7.260 (201.5); 6.996 (1.2); 6.979 (4.6); 6.975 (9.8); 6.958 (5.0); 6.953 (16.0); 6.949 (5.2); 6.932 (8.6); 6.928 (4.3); 5.298 (0.7); 4.367 (11.6); 4.342 (12.8); 3.934 (0.9); 3.857 (2.0); 3.845 (2.1); 3.830 (3.5); 3.820 (3.5); 3.805 (1.9); 3.794 (1.9); 3.650 (2.2); 3.636 (3.1); 3.624 (4.8); 3.609 (3.9); 3.597 (2.9); 3.439 (2.4); 3.427 (2.7); 3.416 (3.1); 3.405 (3.0); 3.390 (2.1); 3.378 (2.0); 2.118 (0.9); 2.110 (1.1); 2.106 (1.7); 2.103 (1.1); 2.094 (1.4); 2.091 (1.4); 2.087 (1.2); 2.083 (2.2); 2.080 (2.4); 2.075 (2.2); 2.072 (2.9); 2.068 (2.2); 2.064 (1.3); 2.060 (1.8); 2.057 (1.8); 2.048 (1.4); 2.045 (2.3); 2.042 (1.4); 2.033 (1.1); 1.901 (1.5); 1.888 (2.3); 1.877 (2.1); 1.866 (3.3); 1.853 (3.0); 1.842 (1.6); 1.831 (1.6); 1.818 (1.0); 1.549 (2.2); 1.333 (1.1); 1.284 (1.3); 1.256 (1.2); 0.008 (2.2); 0.000 (71.5); 0.009 (2.1)
[0441] Example 6: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =8.694 (9.5); 8.689 (9.6); 8.633 (0.6); 8.629 (0.7); 8.621 (0.7); 8.617 (0.7); 8.567 (0.6); 8.562 (0.7); 8.520 (10.9); 8.515 (11.3); 8.508 (9.4); 8.503 (9.3); 8.485 (0.5); 8.481 (0.6); 8.473 (0.6); 8.469 (0.5); 8.207 (8.4); 8.202 (8.5); 7.889 (5.4); 7.888 (5.4); 7.884 (10.2); 7.878 (5.1); 7.787 (5.7); 7.782 (10.5); 7.777 (5.3); 7.521 (1.1); 7.361 (0.6); 7.349 (1.7); 7.333 (2.8); 7.328 (2.6); 7.317 (1.7); 7.312 (5.4); 7.307 (2.2); 7.302 (0.6); 7.296 (2.4); 7.291 (3.3); 7.286 (1.1); 7.284 (0.6); 7.2834 (0.6); 7.2825 (0.6); 7.282 (0.7); 7.281 (0.8); 7.280 (0.8); 7.2794 (0.8); 7.2786 (0.8); 7.278 (0.9); 7.275 (2.2); 7.273 (1.3); 7.272 (1.3); 7.2714 (1.4); 7.2706 (1.6); 7.270 (1.7); 7.269 (2.0); 7.268 (2.2); 7.2674 (2.6); 7.2666 (3.2); 7.266 (4.1); 7.262 (197.8); 7.257 (2.2); 7.256 (1.5); 7.255 (1.1); 7.2544 (0.9); 7.2535 (1.0); 7.253 (0.9); 7.252 (0.7); 7.2512 (0.7); 7.2505 (0.6); 7.211 (0.6); 7.205 (1.5); 7.189 (3.2); 7.184 (2.9); 7.173 (1.8); 7.168 (6.5); 7.163 (2.0); 7.152 (2.9); 7.147 (3.5); 7.140 (0.6); 7.131 (1.7); 6.998 (1.2); 6.977 (2.7); 6.973 (5.8); 6.956 (2.9); 6.951 (9.3); 6.947 (3.1); 6.935 (1.0); 6.930 (5.0); 6.926 (2.6); 6.914 (1.1); 6.892 (0.5); 6.807 (5.6); 6.786 (9.3); 6.770 (1.0); 6.764 (5.0); 6.749 (1.1); 6.728 (0.5); 5.299 (16.0); 4.383 (0.7); 4.360 (0.9); 4.328 (7.0); 4.303 (7.7); 4.243 (8.0); 4.215 (9.4); 4.200 (0.9); 3.922 (1.4); 3.912 (1.4); 3.893 (2.5); 3.884 (2.6); 3.864 (2.1); 3.853 (1.8); 3.837 (2.0); 3.825 (2.0); 3.811 (1.1); 3.800 (1.1); 3.748 (0.9); 3.735 (1.5); 3.722 (2.0); 3.709 (1.8); 3.696 (1.2); 3.616 (7.1); 3.596 (1.7); 3.583 (1.7); 3.570 (1.0); 3.552 (8.2); 3.486 (0.9); 3.473 (1.0); 3.462 (1.5); 3.450 (1.5); 3.437 (0.9); 3.424 (1.5); 3.411 (1.0); 3.400 (1.3); 3.388 (1.3); 3.361 (0.6); 2.557 (0.9); 2.547 (0.9); 2.542 (1.0); 2.533 (1.4); 2.523 (1.9); 2.512 (1.4); 2.508 (1.9); 2.498 (1.9); 2.489 (1.3); 2.484 (1.2); 2.474 (1.1); 2.336 (0.8); 2.332 (0.6); 2.324 (1.3); 2.312 (1.0); 2.308 (1.0); 2.295 (1.5); 2.285 (1.2); 2.278 (0.8); 2.273 (0.7); 2.261 (0.9); 2.250 (0.6); 2.169 (1.2); 2.112 (0.5); 2.100 (0.9); 2.089 (0.8); 2.085 (0.8); 2.082 (0.7); 2.078 (1.1); 2.074 (1.3); 2.070 (1.2); 2.066 (1.5); 2.062 (1.1); 2.058 (0.8); 2.054 (1.1); 2.051 (1.0); 2.039 (1.2); 2.027 (0.6); 1.878 (0.9); 1.865 (1.2); 1.852 (1.1); 1.844 (1.8); 1.829 (1.6); 1.821 (0.8); 1.809 (0.9); 1.795 (0.6); 1.593 (4.4); 1.413 (1.4); 1.346 (1.2); 0.008 (1.9); 0.000 (69.3); 0.007 (0.5); 0.009 (2.0)
[0442] Example 4: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =8.500 (11.0); 8.494 (11.0); 8.425 (6.0); 8.420 (9.1); 8.417 (5.8); 8.328 (13.1); 8.322 (13.2); 8.124 (9.7); 7.521 (0.8); 7.507 (3.4); 7.502 (4.0); 7.501 (4.0); 7.495 (3.2); 7.485 (3.3); 7.480 (4.1); 7.479 (4.0); 7.474 (3.1); 7.400 (3.6); 7.394 (4.6); 7.389 (3.5); 7.378 (3.7); 7.373 (4.5); 7.367 (3.4); 7.345 (1.8); 7.329 (3.7); 7.324 (3.1); 7.313 (2.1); 7.308 (7.5); 7.303 (2.3); 7.292 (2.9); 7.287 (4.2); 7.271 (2.6); 7.262 (144.6); 7.2564 (0.8); 7.2556 (0.6); 7.193 (2.1); 7.176 (4.4); 7.171 (4.0); 7.160 (2.5); 7.155 (9.0); 7.151 (2.8); 7.139 (4.0); 7.134 (4.9); 7.118 (2.4); 6.998 (0.8); 6.973 (3.4); 6.969 (7.2); 6.952 (3.5); 6.947 (11.8); 6.942 (3.8); 6.926 (6.3); 6.921 (3.2); 6.794 (7.3); 6.773 (12.1); 6.751 (6.4); 5.298 (16.0); 4.392 (6.4); 4.367 (7.0); 4.312 (6.7); 4.284 (7.7); 3.941 (1.7); 3.931 (1.8); 3.912 (3.3); 3.902 (3.3); 3.883 (2.8); 3.874 (2.4); 3.856 (2.5); 3.845 (2.4); 3.831 (1.4); 3.819 (1.4); 3.745 (2.4); 3.734 (2.8); 3.730 (2.9); 3.718 (4.7); 3.707 (3.5); 3.703 (3.4); 3.692 (3.0); 3.620 (2.0); 3.609 (2.4); 3.605 (2.5); 3.593 (4.5); 3.581 (3.1); 3.578 (3.2); 3.567 (2.6); 3.486 (2.6); 3.474 (2.9); 3.463 (3.0); 3.459 (2.5); 3.451 (3.0); 3.447 (2.6); 3.436 (2.4); 3.424 (2.4); 3.418 (2.3); 3.406 (2.4); 3.395 (2.6); 3.391 (2.1); 3.383 (2.6); 3.379 (2.1); 3.368 (2.0); 3.356 (1.8); 2.565 (1.2); 2.555 (1.3); 2.550 (1.3); 2.541 (1.8); 2.531 (2.4); 2.520 (1.8); 2.516 (2.4); 2.506 (2.4); 2.497 (1.7); 2.492 (1.5); 2.482 (1.4); 2.342 (0.6); 2.338 (1.0); 2.335 (0.7); 2.326 (1.6); 2.319 (0.7); 2.315 (1.3); 2.310 (1.3); 2.303 (1.5); 2.298 (1.9); 2.287 (1.4); 2.280 (1.0); 2.276 (1.0); 2.272 (0.6); 2.264 (1.2); 2.252 (0.7); 2.117 (0.7); 2.105 (1.2); 2.093 (1.0); 2.090 (1.0); 2.086 (0.9); 2.082 (1.5); 2.078 (1.7); 2.074 (1.6); 2.070 (1.9); 2.067 (1.5); 2.062 (1.0); 2.059 (1.3); 2.055 (1.3); 2.043 (1.6); 2.035 (0.5); 2.032 (0.8); 1.878 (1.1); 1.865 (1.5); 1.852 (1.4); 1.844 (2.2); 1.830 (2.1); 1.821 (1.1); 1.808 (1.1); 1.795 (0.8); 1.532 (3.4); 0.008 (1.6); 0.000 (57.0); 0.009 (1.5)
[0443] Example 460: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =8.208 (15.0); 8.202 (15.1); 8.159 (9.9); 8.153 (10.0); 7.620 (7.2); 7.613 (6.9); 7.599 (8.2); 7.592 (8.0); 7.519 (5.1); 7.432 (8.3); 7.425 (8.1); 7.411 (10.8); 7.404 (10.5); 7.361 (0.6); 7.350 (1.0); 7.345 (0.6); 7.317 (11.5); 7.316 (11.6); 7.310 (2.4); 7.306 (1.0); 7.302 (1.1); 7.297 (10.3); 7.295 (10.9); 7.290 (1.4); 7.287 (1.1); 7.280 (18.3); 7.279 (18.9); 7.275 (3.4); 7.274 (3.1); 7.273 (3.1); 7.2722 (3.6); 7.2715 (4.0); 7.271 (4.4); 7.270 (4.9); 7.268 (6.5); 7.2674 (7.1); 7.2666 (8.2); 7.266 (10.1); 7.265 (12.0); 7.260 (971.1); 7.234 (1.0); 7.232 (1.0); 7.175 (4.2); 7.168 (4.8); 7.162 (4.5); 7.154 (8.3); 7.146 (4.7); 7.140 (4.6); 7.132 (4.4); 7.011 (2.2); 7.001 (4.5); 6.996 (6.1); 6.993 (2.7); 6.989 (6.8); 6.983 (4.9); 6.978 (10.4); 6.971 (6.4); 6.968 (6.6); 6.965 (7.2); 6.960 (12.5); 6.953 (11.7); 6.950 (9.8); 6.942 (12.9); 6.938 (2.7); 6.932 (10.3); 6.924 (5.0); 6.921 (10.2); 6.910 (9.8); 6.902 (2.1); 6.899 (3.4); 6.887 (3.0); 6.853 (3.0); 6.846 (2.8); 6.839 (3.3); 6.832 (5.6); 6.824 (2.9); 6.818 (3.2); 6.811 (2.7); 4.353 (15.3); 4.336 (16.0); 4.143 (10.4); 4.121 (11.2); 3.751 (4.6); 3.735 (7.2); 3.713 (6.9); 3.696 (4.0); 3.654 (2.1); 3.645 (2.1); 3.632 (2.1); 3.624 (3.3); 3.617 (2.3); 3.604 (2.0); 3.594 (1.9); 3.528 (3.0); 3.425 (1.4); 3.401 (2.2); 2.370 (1.3); 2.360 (1.4); 2.355 (1.5); 2.346 (2.6); 2.335 (2.5); 2.325 (2.1); 2.320 (2.6); 2.311 (3.6); 2.302 (2.0); 2.297 (1.9); 2.287 (1.8); 2.185 (1.2); 2.175 (2.1); 2.159 (1.9); 2.145 (3.3); 2.138 (2.6); 2.131 (2.0); 2.124 (4.5); 2.110 (6.9); 2.104 (6.3); 2.091 (8.5); 2.080 (5.1); 2.075 (3.8); 2.070 (5.7); 2.056 (3.3); 2.046 (1.0); 2.035 (1.3); 2.005 (0.6); 1.544 (105.2); 1.361 (5.1); 1.276 (3.0); 0.146 (1.1); 0.069 (2.4); 0.049 (0.7); 0.033 (0.5); 0.008 (11.2); 0.006 (3.9); 0.0054 (4.4); 0.0046 (5.1); 0.000 (382.1); 0.005 (4.7); 0.006 (3.3); 0.007 (2.9); 0.009 (10.6); 0.011 (1.4); 0.0116 (1.1); 0.0124 (1.0); 0.013 (1.0); 0.014 (0.8); 0.015 (0.6); 0.016 (0.7); 0.020 (0.6); 0.023 (0.6); 0.028 (0.6); 0.150 (1.1)
[0444] Example 1 (threo): .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =8.189 (8.0); 8.183 (8.1); 7.892 (9.1); 7.886 (9.8); 7.875 (4.1); 7.868 (3.9); 7.856 (4.5); 7.853 (4.9); 7.850 (4.5); 7.847 (4.4); 7.835 (4.1); 7.828 (3.9); 7.773 (4.6); 7.766 (4.2); 7.754 (5.1); 7.752 (5.6); 7.748 (5.0); 7.745 (4.8); 7.733 (4.7); 7.727 (4.3); 7.521 (1.1); 7.339 (2.2); 7.323 (4.4); 7.318 (3.9); 7.307 (2.6); 7.302 (9.0); 7.297 (2.9); 7.286 (3.9); 7.281 (5.2); 7.262 (183.6); 7.189 (2.7); 7.173 (5.6); 7.168 (5.3); 7.157 (3.2); 7.152 (11.3); 7.147 (3.7); 7.136 (5.3); 7.131 (6.2); 7.115 (3.1); 7.019 (6.0); 7.011 (5.9); 6.998 (6.2); 6.990 (5.7); 6.968 (4.3); 6.964 (9.0); 6.947 (4.6); 6.942 (14.6); 6.937 (4.8); 6.920 (7.9); 6.916 (3.9); 6.870 (7.5); 6.862 (7.4); 6.849 (7.1); 6.841 (7.0); 6.787 (9.6); 6.765 (16.0); 6.743 (8.5); 4.359 (10.5); 4.334 (11.5); 4.280 (13.0); 4.252 (15.2); 3.923 (2.4); 3.913 (2.6); 3.895 (4.7); 3.885 (4.6); 3.866 (2.4); 3.857 (4.0); 3.846 (2.1); 3.831 (3.2); 3.820 (3.2); 3.806 (1.8); 3.794 (1.8); 3.744 (3.3); 3.733 (3.8); 3.729 (3.9); 3.717 (6.5); 3.706 (4.7); 3.702 (4.6); 3.691 (4.0); 3.619 (2.5); 3.608 (3.0); 3.604 (3.2); 3.592 (5.5); 3.581 (3.9); 3.577 (4.0); 3.566 (3.3); 3.485 (3.4); 3.472 (3.8); 3.461 (4.1); 3.457 (3.4); 3.449 (4.1); 3.445 (3.5); 3.434 (3.2); 3.422 (3.2); 3.414 (2.9); 3.402 (3.0); 3.391 (3.3); 3.387 (2.6); 3.379 (3.2); 3.375 (2.7); 3.364 (2.4); 3.352 (2.2); 2.569 (1.6); 2.559 (1.8); 2.554 (1.8); 2.545 (2.6); 2.535 (3.3); 2.524 (2.6); 2.520 (3.3); 2.511 (3.4); 2.502 (2.3); 2.497 (2.1); 2.487 (2.0); 2.332 (0.8); 2.328 (1.4); 2.325 (1.0); 2.317 (2.3); 2.309 (1.1); 2.305 (1.8); 2.300 (1.8); 2.293 (2.1); 2.288 (2.8); 2.283 (2.5); 2.277 (2.0); 2.270 (1.4); 2.266 (1.3); 2.262 (0.8); 2.254 (1.7); 2.246 (0.7); 2.242 (1.0); 2.239 (0.5); 2.104 (0.9); 2.093 (1.6); 2.081 (1.3); 2.077 (1.3); 2.074 (1.2); 2.070 (1.9); 2.066 (2.1); 2.062 (2.1); 2.058 (2.5); 2.054 (1.9); 2.050 (1.2); 2.046 (1.7); 2.043 (1.7); 2.031 (1.9); 2.019 (1.0); 1.879 (1.4); 1.866 (1.9); 1.854 (1.9); 1.844 (2.9); 1.830 (2.8); 1.821 (1.4); 1.810 (1.4); 1.796 (1.0); 1.584 (0.6); 1.564 (0.5); 1.540 (0.8); 1.464 (3.7); 1.333 (0.8); 1.284 (1.0); 1.274 (0.5); 1.255 (2.1); 0.008 (2.1); 0.000 (65.5); 0.009 (1.7)
[0445] Example 14: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =8.069 (3.3); 8.066 (3.6); 8.063 (3.8); 8.060 (3.4); 7.879 (3.5); 7.873 (3.3); 7.859 (3.5); 7.853 (3.3); 7.791 (2.8); 7.785 (4.4); 7.767 (16.0); 7.761 (2.5); 7.520 (0.6); 7.355 (0.9); 7.339 (1.8); 7.334 (1.6); 7.323 (1.1); 7.318 (3.7); 7.313 (1.2); 7.302 (1.6); 7.297 (2.1); 7.281 (1.2); 7.261 (110.6); 7.226 (1.1); 7.210 (2.4); 7.205 (1.9); 7.194 (1.2); 7.189 (4.2); 7.184 (1.3); 7.173 (1.9); 7.168 (2.3); 7.152 (1.1); 6.997 (0.6); 6.979 (1.8); 6.975 (3.9); 6.958 (1.9); 6.953 (6.3); 6.948 (2.0); 6.932 (3.4); 6.927 (1.7); 6.825 (3.9); 6.803 (6.5); 6.781 (3.5); 5.299 (7.8); 4.368 (4.6); 4.343 (5.0); 4.276 (5.3); 4.247 (6.1); 4.044 (1.0); 3.933 (1.7); 3.919 (0.9); 3.909 (0.9); 3.891 (1.8); 3.881 (1.7); 3.862 (1.0); 3.855 (1.2); 3.845 (0.9); 3.831 (1.4); 3.819 (1.3); 3.806 (0.8); 3.794 (0.7); 3.756 (1.2); 3.745 (1.4); 3.741 (1.4); 3.729 (2.2); 3.718 (1.7); 3.714 (1.7); 3.703 (1.5); 3.650 (1.0); 3.638 (1.3); 3.635 (1.3); 3.623 (2.1); 3.611 (1.6); 3.609 (1.6); 3.597 (1.2); 3.484 (1.2); 3.472 (1.3); 3.461 (1.5); 3.457 (1.3); 3.449 (1.5); 3.445 (1.4); 3.439 (1.3); 3.434 (1.3); 3.427 (1.4); 3.422 (1.3); 3.416 (1.4); 3.412 (1.1); 3.404 (1.3); 3.401 (1.1); 3.389 (0.9); 3.378 (0.9); 2.556 (0.6); 2.546 (0.7); 2.541 (0.7); 2.532 (1.1); 2.522 (1.3); 2.511 (1.0); 2.507 (1.3); 2.498 (1.4); 2.488 (0.9); 2.484 (0.8); 2.473 (0.7); 2.323 (0.5); 2.312 (0.9); 2.300 (0.7); 2.295 (0.7); 2.288 (0.8); 2.284 (1.1); 2.277 (0.9); 2.273 (0.8); 2.266 (0.5); 2.261 (0.5); 2.249 (0.7); 2.107 (0.7); 2.095 (0.5); 2.092 (0.5); 2.084 (0.9); 2.080 (0.9); 2.076 (0.8); 2.072 (1.1); 2.069 (0.9); 2.060 (0.7); 2.057 (0.7); 2.049 (0.5); 2.045 (0.9); 1.902 (0.6); 1.889 (0.9); 1.877 (0.8); 1.867 (1.3); 1.853 (1.2); 1.843 (0.6); 1.832 (0.6); 1.562 (0.9); 0.008 (1.1); 0.000 (37.9); 0.009 (1.1)
[0446] Example 14 (three): .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =7.791 (2.8); 7.785 (4.4); 7.767 (16.0); 7.760 (2.5); 7.519 (0.7); 7.272 (0.6); 7.271 (0.6); 7.270 (0.7); 7.2694 (0.8); 7.2687 (0.9); 7.268 (1.0); 7.267 (1.2); 7.266 (1.5); 7.265 (1.8); 7.261 (119.0); 7.254 (0.8); 7.253 (0.6); 7.227 (1.0); 7.210 (2.1); 7.206 (2.0); 7.194 (1.2); 7.189 (4.3); 7.185 (1.4); 7.173 (2.0); 7.168 (2.4); 7.152 (1.2); 6.997 (0.7); 6.825 (4.0); 6.803 (6.6); 6.782 (3.5); 4.275 (5.3); 4.247 (6.2); 3.919 (0.9); 3.909 (1.0); 3.891 (1.8); 3.881 (1.7); 3.863 (0.8); 3.853 (0.8); 3.758 (0.8); 3.744 (1.1); 3.732 (1.6); 3.720 (1.3); 3.706 (1.0); 3.487 (0.8); 3.475 (0.9); 3.462 (1.1); 3.451 (1.2); 3.436 (0.7); 3.424 (0.7); 2.558 (0.6); 2.548 (0.7); 2.544 (0.7); 2.534 (1.1); 2.524 (1.3); 2.514 (1.0); 2.510 (1.3); 2.500 (1.4); 2.491 (0.9); 2.486 (0.8); 2.476 (0.7); 2.325 (0.5); 2.313 (0.9); 2.302 (0.7); 2.296 (0.7); 2.293 (0.6); 2.289 (0.8); 2.285 (1.1); 2.278 (1.0); 2.274 (0.8); 2.267 (0.5); 2.250 (0.7); 1.550 (3.5); 1.333 (0.8); 0.008 (1.2); 0.000 (42.6); 0.009 (1.2)
[0447] The retention time (Rt) given in the Rt table below for the enantiomer of the formula (I) in question is given in minutes (min), where the letter a, b, c or d given after the forward slash after the retention time refers to the conditions stated above for HPLC on a chiral column and the respective mobile phase stated above, i.e. mobile phase a, mobile phase b, mobile phase c or mobile phase d.
TABLE-US-00006 RT TABLE Rt in min, where R.sup.1 is in each case hydrogen No. Q(R.sup.2).sub.n (R.sup.3).sub.m erythro-1 erythro-2 threo-1 threo-2 1 6-fluoropyridin-3-yl 2.6-F.sub.2 13.319/c 16.632/c 18.098/c 25.226/c 6 5-bromopyridin-3-yl 2.6-F.sub.2 12.165/c 14.334/c 16.747/c 22.114/c 14 5-chloro-6-fluoropyridin-3-yl 2.6-F.sub.2 29.016/d 32.963/d 43.280/d 45.023/d 85 pyridin-3-yl 2.6-F.sub.2 11.160/b 16.121/b 17.456/b 32.753/b 460 6-chloropyridin-3-yl 2.5-F.sub.2 11.890/c 14.276/c 23.034/c 27.864/c 472 5-chloro-6-fluoropyridin-3-yl 2.5-F.sub.2 6.190/c 6.827/c 11.531/c 13.014/c
FORMULATION EXAMPLES
[0448] a) A dust is obtained by mixing 10 parts by weight of a compound of the formula (I) and 90 parts by weight of talc as inert substance and comminuting the mixture in a hammer mill. [0449] b) A wettable powder which is readily dispersible in water is obtained by mixing 25 parts by weight of a compound of the formula (I), 64 parts by weight of kaolin-containing quartz as inert substance, 10 parts by weight of potassium lignosulfonate and 1 part by weight of sodium oleoylmethyltaurate as wetting agent and dispersant, and grinding the mixture in a pinned-disk mill. [0450] c) A readily water-dispersible dispersion concentrate is obtained by mixing 20 parts by weight of a compound of the formula (I) with 6 parts by weight of alkylphenol poly glycol ether (Triton X 207), 3 parts by weight of isotridecanol polyglycol ether (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling range for example about 255 to about 277 C.) and grinding the mixture in a ball mill to a fineness of below 5 microns. [0451] d) An emulsifiable concentrate is obtained from 15 parts by weight of a compound of the formula (I), 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of oxyethylated nonylphenol as emulsifier. [0452] e) Water-dispersible granules are obtained by mixing [0453] 75 parts by weight of a compound of the formula (I), [0454] 10 parts by weight of calcium lignosulfonate, [0455] 5 parts by weight of sodium lauryl sulfate, [0456] 3 parts by weight of polyvinyl alcohol and [0457] 7 parts by weight of kaolin, [0458] grinding the mixture in a pinned-disk mill, and granulating the powder in a fluidized bed by spray application of water as a granulating liquid. [0459] f) Water-dispersible granules are also obtained by homogenizing and precomminuting, in a colloid mill, [0460] 25 parts by weight of a compound of the formula (I), [0461] 5 parts by weight of sodium 2,2-dinaphthylmethane-6,6-disulfonate, [0462] 2 parts by weight of sodium oleoylmethyltaurinate, [0463] 1 part by weight of polyvinyl alcohol, [0464] 17 parts by weight of calcium carbonate and [0465] 50 parts by weight of water, [0466] then grinding the mixture in a bead mill and atomizing and drying the resulting suspension in a spray tower by means of a one-phase nozzle.
[0467] Biological Examples
[0468] Herbicidal Pre-Emergence Action
[0469] Seeds of monocotyledonous and dicotyledonous weed plants and crop plants were placed in wood-fiber pots in sandy loam and covered with soil. The compounds (I) according to the invention, formulated in the form of wettable powders (WP), were then applied as aqueous suspension or emulsion at a water application rate of 600 l/ha (converted) with the addition of 0.2% of wetting agent to the surface of the covering soil.
[0470] After the treatment, the pots were placed in a greenhouse and kept under good growth conditions for the test plants. After about 3 weeks, the effect was scored visually in comparison with untreated controls as percentages. For example, 100% activity=the plants have died, 50% herbicidal activity or damage=the plants have been reduced by 50% or the plant mass has been reduced by 50%, 0% activity=like control plants.
[0471] The results obtained show that compounds (I) according to the invention and their salts, in particular the compounds according to the invention characterized as preferred, have good to very good herbicidal activity against harmful plants at an application rate of 320 g or less per hectare, generally also even at a respective application rate of 80 g/ha.
[0472] The biological tests were carried out in each case separately with the compounds according to the invention below which, by virtue of the good to very good herbicidal activity thereof, are particularly preferred according to the invention:
[0473] Compound No. 1, 2, 3, 4, 5, 6, 14, 15, 85, 86, 186, 460, 461, 462, 463, 472, 543, 544, 1833, 1834, 1835, 1836, 1873, 1875, 1876, 1915, 1961, 1962, 1963, 1964, 2001, 2003, 2004, 2005, 2006 and 2043.
[0474] The biological tests were in each case carried out separately with the following compounds according to the invention: Compound No. 1 erythro+threo-1, 1 threo-2, 14 erythro-1+erythro-2, 14 threo-1, 14 threo-2, 15 erythro-1+erythro-2, 15 threo-1+threo-2, 460 erythro, 460 erythro-1, 460 threo, 460 threo-1, 460 threo-2, 472 erythro-1, 472 erythro-2, 472 threo-1, 472 threo-2, 6 erythro-2, 6 erythro-1, 6 threo-1, 6 threo-2 and 85 erythro.
[0475] Here, these compounds according to the invention were in each case employed in the biological tests as a component of a wettable powder (WP formulation).
[0476] At an application rate of 320 g/ha, all the compounds according to the invention mentioned showed 80% to 100% herbicidal activity in the biological tests, against one, more than one or all of the harmful plants below:
ALOMY=Alopecurus myosuroides
AVEFA=Avena fatua
CYPES=Cyperus esculentus
ECHCG=Echinochloa crus-galli
LOLMU=Lolium multiflorum
SETVI=Setaria viridis
ABUTH=Abutilon theophrasti
AMARE=Amaranthus retroflexus
POLCO=Polygonum convolvulus (=Fallopia convolvulus)
STEME=Stellaria media
VIOTR=Viola tricolor
VERPE=Veronica persica
[0477] What was determined was the respective herbicidal activity, in each case at the same point in time after application of the formulation in question, i.e. the damage to the respective harmful plant in %.
[0478] Furthermore, the compounds according to the invention mentioned above were applied to the following useful plants, in each case at the application rates mentioned.
ORYSA=Oryza sativa (common rice)
TRZAS=triticum aestivum (spring) (summer wheat)
ZEAMX=Zea mays (maize)
BRSNW=Brassica napus subsp. napus (winter) (winter oilseed rape)
[0479] Here, the observed damage to the respective useful plants was within the acceptable range and was generally assessed as low (generally in the range from 0 to 20%, mostly in the range from 0 to 10%).
[0480] Herbicidal Post-Emergence Action
[0481] Seeds of monocotyledonous and dicotyledonous weeds and crop plants were placed in sandy loam in wood-fiber pots, covered with soil and cultivated in a greenhouse under good growth conditions. 2 to 3 weeks after sowing, the test plants were treated at the one-leaf stage, where the compounds according to the invention, formulated in the form of wettable powders (WP), were applied by spraying as aqueous suspension or emulsion at a water application rate of 600 l/ha (converted) with the addition of 0.2% of wetting agent to the green parts of the plants. After the test plants had been kept in the greenhouse under optimum growth conditions for about 3 weeks, the activity of the preparations was rated visually in comparison to untreated controls in percent (%). For example, 100% activity=the plants have died, 50% herbicidal activity or damage=the plants have been reduced by 50% or the plant mass has been reduced by 50%, 0% activity=like control plants.