Compounds with nematicidal activity

The present invention relates to the use of predominantly known pyridyl carboxamide derivatives as nematicides, compositions containing such compounds and methods for the control of nematodes.

2. Description of Related Art

Nematodes cause a substantial loss in agricultural product including food and industrial crops and are combated with chemical compounds having nematicidal activity. To be useful in agriculture these compounds should have a high activity, a broad spectrum activity against different strains of nematodes and should not be toxic to non-target organisms.

The use of certain N-2-(pyridyl)ethyl-carboxamide derivatives for controlling nematodes is described in EP 2 132 987 A1.

Most of the compounds of formula (I) described below are known from WO 2001/011965 A1 (later, e.g. in the Tables, referred to as P1), WO 2005/058828 A1 (P2), WO2005/014545 A2 (P3), WO 2005/103004 A1 (P4), WO 2006/122952 A1 (P5), EP 2 289 880 A1 (P6), WO 2006/008191 A1 (P7) and WO 2006/008192 A1 (P8). There it is stated that they can be used as fungicides. Recently WO 2012/118139 was published. It discloses compounds with nematicidal activity.

SUMMARY

Surprisingly it has now been found that these compounds exhibit nematicidal activity and can therefore be used to control nematodes.

It was also found that the compounds of formula (I) exhibit activity against bacteria and viruses and can be used as bactericides and as virucides.

Accordingly, the present invention relates to the use of a compound of formula (I)

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wherein

B represents 2-pyridyl, 3-pyridyl, or 4-pyridyl,
X is selected from the group consisting of halogen, nitro, cyano, hydroxy, amino, —SH, —SF₅, —CHO, —OCHO, —NHCHO, —COOH, —CONH₂, —CONH(OH), —OCONH₂, (hydroxyimino)-C₁-C₆-alkyl, C₁-C₈-alkyl, C₁-C₈-halogenoalkyl having 1 to 5 halogen atoms, C₂-C₈-alkenyl, C₂-C₈-alkynyl, C₁-C₈-alkylamino, di-(C₁-C₈-alkyl)amino, C₁-C₈-alkoxy, C₁-C₈-halogenoalkoxy having 1 to 5 halogen atoms C₂-C₈-alkenyloxy, C₂-C₈-halogenoalkenyloxy having 1 to 5 halogen atoms, C₃-C₈-alkynyloxy, C₃-C₈-halogenoalkynyloxy having 1 to 5 halogen atoms, C₃-C₈-cycloalkyl, C₃-C₈-halogenocycloalkyl having 1 to 5 halogen atoms, C₁-C₈-alkylcarbonyl, C₁-C₈halogenoalkylcarbonyl having 1 to 5 halogen atoms, —CONH(C₁-C₈-alkyl), —CON(C₁-C₈-alkyl)₂, —CONH(OC₁-C₈-alkyl), —CON(OC₁-C₈-alkyl)(C₁-C₈-alkyl), C₁-C₈-alkoxycarbonyl, C₁-C₈-halogenoalkoxycarbonyl having 1 to 5 halogen atoms, C₁-C₈-alkylcarbonyloxy, C₁-C₈-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, C₁-C₈-alkylcarbonylamino, C₁-C₈-halogenoalkylcarbonylamino having 1 to 5 halogen atoms, —COCNH(C₁-C₈-alkyl), —OCON(C₁-C₈-alkyl)₂, —OCONH(OC₁-C₈-alkyl), —OCO(OC₁-C₈alkyl), —S—C₁-C₈-alkyl, —S—C₁-C₈-halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C₁-C₈-alkyl, —S(O)—C₁-C₈-halogenoalkyl having 1 to 5 halogen atoms, —S(O)₂—C₁-C₈-alkyl, —S(O)₂—C₁-C₈-halogenoalkyl having 1 to 5 halogen atoms, (C₁-C₆-alkoxyimino)-C₁-C₆-alkyl, (C₂-C₆-alkenyloxyimino)-C₁-C₆-alkyl, (C₃-C₆-alkynyloxyimino)-C₁-C₆-alkyl, (benzyloxyimino)-C₁-C₆-alkyl, benzyloxy, —S-benzyl, benzylamino, phenoxy, —S-phenyl and phenylamino,
n is 1, 2, 3 or 4 and if n is 2, 3, or 4 then the substituents X may be the same or different,
R¹and R²are the same or different and are selected from the group consisting of hydrogen, halogen, cyano, hydroxy, amino, —SH, —CHO, —OCHO, —NHCHO, —COOH, —CONH₂, —CONH(OH), —OCONH₂, (hydroxyimino)-C₁-C₆-alkyl group, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkylamino, di-(C₁-C₆-alkyl)amino, C₁-C₆-alkoxy, C₁-C₆-halogenoalkyl having 1 to 5 halogen atoms, C₁-C₆-halogenoalkoxy having 1 to 5 halogen atoms, C₂-C₆-alkenyloxy, C₂-C₆-halogenoalkenyloxy having 1 to 5 halogen atoms, C₃-C₆-alkynyloxy, C₃-C₆-halogenoalkynyloxy having 1 to 5 halogen atoms, C₃-C₆-cycloalkyl, C₃-C₆-halogenocycloalkyl having 1 to 5 halogen atoms, C₃-C₆-cycloalkyl-C₁-C₆-alkyl, C₃-C₆-halogenocycloalkyl-C₁-C₆-alkyl having 1 to 5 halogen atoms, C₁-C₆-alkylcarbonyl, C₁-C₆-halogenoalkylcarbonyl having 1 to 5 halogen atoms, —CONH(C₁-C₆-alkyl), —CON(C₁-C₆-alkyl)₂, —CONH(OC₁-C₆-alkyl), —CON(OC₁-C₆-alkyl)(C₁-C₆-C₁-C₆-alkoxycarbonyl, a C₁-C₆-halogenoalkoxycarbonyl having 1 to 5 halogen atoms, —OC(O)—C₁-C₆-alkyl, —OC(O)—C₁-C₆-halogenoalkyl having 1 to 5 halogen atoms, —NHC(O)—C₁-C₆-alkyl, —NHC(O)—C₁-C₆-halogenoalkyl having 1 to 5 halogen atoms, —OCONH(C₁-C₆-alkyl), —OCON(C₁-C₆-alkyl)₂, —OCONH(OC₁-C₆-alkyl), OCO(OC₁-C₆-alkyl), —S—C₁-C₆-alkyl, —S—C₁-C₆-halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C₁-C₆-alkyl, —S(O)—C₁-C₆-halogenoalkyl having 1 to 5 halogen atoms, —S(O)₂—C₁-C₆-alkyl, —S(O)₂—C₁-C₆-halogenoalkyl having 1 to 5 halogen atoms, benzyl, benzyloxy, —S-benzyl, —S(O)-benzyl, —S(O)₂-benzyl, benzylamino, phenoxy, —S-phenyl, —S(O)-phenyl, —S(O)₂-phenyl, phenylamino, phenylcarbonylamino, 2,6-dichlorophenyl-carbonylamino, 2-chlorophenyl-carbonylamino and phenyl or
R¹and R²together with the carbon atom to which they are bonded form a 3-, 4-, 5- or 6-membered carbocycle,
R³and R⁴are the same or different and are selected from the group consisting of hydrogen, halogen, cyano, hydroxy, amino, —SH, —CHO, —COOH, —CONH₂, —CONH(OH), —OCONH₂, (hydroxyimino)-C₁-C₆-alkyl, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkylamino, di-(C₁-C₆-alkyl)amino, C₁-C₆-alkoxy, hydroxy-C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-halogenoalkyl having 1 to 5 halogen atoms, C₁-C₆-halogenoalkoxy having 1 to 5 halogen atoms, C₂-C₆-alkenyloxy, C₂-C₆-halogenoalkenyloxy having 1 to 5 halogen atoms, C₃-C₆-alkynyloxy, C₃-C₆-halogenoalkynyloxy having 1 to 5 halogen atoms, C₃-C₆-cycloalkyl, C₃-C₆-halogenocycloalkyl having 1 to 5 halogen atoms, C₁-C₆-alkylcarbonyl, C₁-C₆-halogenoalkylcarbonyl having 1 to 5 halogen atoms, —CONH(C₁-C₆-alkyl), —CON(C₁-C₆-alkyl)₂, —CONH(OC₁-C₆-alkyl), —CON(OC₁-C₆-alkyl)(C₁-C₆-alkyl), C₁-C₆-alkoxycarbonyl, C₁-C₆-halogenoalkoxycarbonyl having 1 to 5 halogen atoms, —OC(O)—C₁-C₆-alkyl, —OC(O)—C₁-C₆-halogenoalkyl having 1 to 5 halogen atoms, —NHC(O)—C₁-C₆-alkyl, —NHC(O)—C₁-C₆-halogenoalkyl having 1 to 5 halogen atoms, —OCONH(C₁-C₆-alkyl), —OCON(C₁-C₆-alkyl)₂, —OCONH(OC₁-C₆-alkyl), OCO(OC₁-C₆-alkyl), —S—C₁-C₆-alkyl, —S—C₁-C₆-halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C₁-C₆-alkyl, —S(O)—C₁-C₆-halogenoalkyl having 1 to 5 halogen atoms, —S(O)₂—C₁-C₆-alkyl, —S(O)₂—C₁-C₆-halogenoalkyl having 1 to 5 halogen atoms, benzyl, benzyloxy, —S-benzyl, —S(O)-benzyl, —S(O)₂-benzyl, benzylamino, phenoxy, —S-phenyl, —S(O)-phenyl, —S(O)₂-phenyl, phenylamino, phenylcarbonylamino, 2-chlorophenyl-carbonylamino, 2,6-dichlorophenyl-carbonylamino and phenyl;
R⁵is selected from the group consisting of hydrogen, cyano, —CHO, —OH, C₁-C₆-alkyl, C₁-C₆-halogenoalkyl having 1 to 5 halogen atoms, C₁-C₆-alkoxy, C₁-C₆-halogenoalkoxy having 1 to 5 halogen atoms, C₃-C₇-cycloalkyl, C₃-C₇-halogenocycloalkyl having 1 to 5 halogen atoms, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₃-C₇-cycloalkyl-C₁-C₆-alkyl, cyano-C₁-C₆-alkyl, amino-C₁-C₆-alkyl, C₁-C₆-alkylamino-C₁-C₆-alkyl, di-(C₁-C₆-alkyl)amino-C₁-C₆-alkyl, C₁-C₆-alkylcarbonyl, C₁-C₆-halogenoalkylcarbonyl having 1 to 5 halogen atoms, C₁-C₆-alkoxycarbonyl, benzyloxycarbonyl, C₁-C₆-alkoxy-C₁-C₆-alkylcarbonyl, —S(O)₂—C₁-C₆-alkyl, and —S(O)₂—C₁-C₆-halogenoalkyl having 1 to 5 halogen atoms;
A represents a phenyl group of formula (A1)

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wherein

R is selected from the group consisting of halogen, nitro, —OH, NH₂, SH, SF₅, CHO, OCHO, NHCHO, COOH, cyano, C₁-C₈-alkyl, C₁-C₈-halogenoalkyl having 1 to 5 halogen atoms, C₂-C₈-alkenyl, C₂-C₈-alkynyl, C₃-C₆-cycloalkyl, —S—C₁-C₈-alkyl, —S—C₁-C₈-halogenoalkyl having 1 to 5 halogen atoms, C₁-C₈-alkoxy, C₁-C₈-halogenoalkoxy having 1 to 5 halogen atoms, C₁-C₈-alkoxy-C₂-C₈-alkenyl, C₁-C₈-alkoxycarbonyl, C₁-C₈-halogenoalkoxycarbonyl having 1 to 5 halogen atoms, C₁-C₈-alkylcarbonyloxy, C₁-C₈-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, —S(O)—C₁-C₈-alkyl, —S(O)—C₁-C₈-halogenoalkyl having 1 to 5 halogen atoms, —S(O)₂—C₁-C₈-alkyl, —S(O)₂—C₁-C₈-halogenoalkyl having 1 to 5 halogen atoms, C₁-C₈-alkylsulfonamide, —NH(C₁-C₈-alkyl), N(C₁-C₈-alkyl)₂, phenyl (optionally substituted by C₁-C₆-alkoxy) and phenoxy, or two R bonded to adjacent carbon atoms together represent —O(CH₂)_pO—, wherein p represents 1 or 2,
m is 0, 1, 2, 3, 4 or 5 and if m is 2, 3, 4, or 5 then the substituents R may be the same or different;
with the proviso, that, when B represents 2-pyridyl, then
- at least one of R¹, R², R³, R⁴and R⁵is not a hydrogen atom and
- R²and R³may also together with the carbon atoms to which they are bonded form a 3-, 4-, 5-, 6- or 7-membered carbocycle,
  
  with the proviso, that when B represents 3-pyridyl, then
- R³and R⁴may also together with the carbon atom to which they are bonded form a 3-, 4-, 5- or 6-membered carbocycle,
  
  with the proviso, that, when B represents 4-pyridyl, then
- R²and R³may also together with the carbon atoms to which they are bonded form a 3-, 4-, 5-, 6- or 7-membered carbocycle or
- R³and R⁴may also together with the carbon atom to which they are bonded form a 3-, 4-, 5- or 6-membered carbocycle,
  
  against nematodes.

BRIEF DESCRIPTION OF THE DRAWINGS

FIGS. 1-16 show chemical structures and mass spectrometry graphs for Compound Nos. Ia-197 through Ia-212, respectively, as further described herein.

FIGS. 17 and 18 show chemical structures and mass spectrometry graphs for Compound Nos. IIa40 and IIa41, respectively, as further described herein.

FIG. 19 shows mass spectrometry graph for Compound No. Int-11, as further described herein.

FIGS. 20-22 show chemical structures and mass spectrometry graphs for Compound Nos. Int-12 through Int-14, respectively, as further described herein.

FIG. 23 shows chemical structure and mass spectrometry graph for Compound No. IIb-34×HCl, as further described herein.

FIGS. 24-27 show chemical structures and mass spectrometry graphs for Compound No. Int-15, Int-16, Int-18, and Int-19, respectively, as further described herein.

FIG. 28 shows chemical structure and mass spectrometry graph for Compound No. IIb-35×HCl, as further described herein.

DETAILED DESCRIPTION OF A PREFERRED EMBODIMENT

In particular the present invention relates to the use of compounds of formula (I) against phytopathogenic nematodes, i.e. against nematodes which damage plants or parts of plants (plant nematodes).

Any of the compounds according to the invention can exist in one or more optical or chiral isomer forms depending on the number of asymmetric centres in the compound. The invention thus relates equally to all the optical isomers and to their racemic or scalemic mixtures (the term “scalemic” denotes a mixture of enantiomers in different proportions), and to the mixtures of all the possible stereoisomers, in all proportions. The diastereoisomers and/or the optical isomers can be separated according to the methods which are known per se by a person ordinary skilled in the art.

The invention also relates to the use of salts, N-oxides, metal complexes and metalloid complexes of compounds of formula (I) against nematodes.

A preferred embodiment of the present invention is the use of compounds of formula (Ia)

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wherein R, R¹, R², R³, R⁴, R⁵X, n, and m have the meanings given above, for the control of nematodes. Another preferred embodiment of the present invention is the use of compounds of formula (Ib)

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wherein R, R¹, R², R³, R⁴, R⁵X, n, and m have the meanings given above, for the control of nematodes. Another preferred embodiment of the present invention are compounds of formula (Ib-a1)

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wherein R, R¹, R², R³, R⁴, R⁵, n and m have the meanings given above and X represents halogen. Preferably n represents 3 in which case the halogen-atoms (in particular chloro-atoms) are in the 2- and 4-position.

Another preferred embodiment of the present invention are compounds of formula (Ib-a2)

Another preferred embodiment of the present invention is the use of compounds of formula (Ic)

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wherein R, R¹, R², R³, R⁴, R⁵X, n, and m have the meanings given above, for the control of nematodes. Other preferred embodiments of the present invention are compounds of formula (I), (Ia), (Ib), (Ib-a1), (Ib-a2) and (Ic) in which R¹and R²both represent halogen and in particular R¹and R²both represent fluorine.

Compounds of formula (I) can for example be prepared by reacting a compound of formula (II)

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wherein X, n, R¹, R², R³, R⁴, and R⁵are defined as above,

with a compound of formula (III)

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wherein A is defined as above, and

L is a leaving group selected from the group consisting of halogen, hydroxyl, optionally substituted alkyl, optionally substituted benzyl and a group of formula

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usually in the presence of a base, a condensing agent and in the presence of a solvent.

This process and other processes for the preparation of the compounds of formula (I) as well as intermediates for the preparation of compounds of formula (I) are described in more detail in WO 2001/011965 A1 (P1), WO 2005/058828 A1 (P2), WO2005/014545 A2 (P3), WO 2005/103004 A1 (P4), WO 2006/122952 A1 (P5), EP 2 289 880 A1 (P6), WO 2006/008191 A1 (P7), WO 2006/008192A1 (P8), WO 2004/074280 A1 (P9), WO 2005/058833 A2 (P10), WO 2005/085238 A1 (P11), WO 2005/103006 A1 (P12), WO 2006/122955 A1 (P13), WO 2006/008194 A1 (P14), WO 2006/008193 A1 (P15) and WO 2006/067103 A2 (P16).

In compounds of formula (I), the use of which is preferred, R, R¹, R², R³, R⁴, R⁵X, B, n and m have the following meanings.

B represents 2-pyridyl, 3-pyridyl, or 4-pyridyl.
X is selected from the group consisting of halogen, nitro, cyano, C₁-C₄-alkyl, C₁-C₄-halogenoalkyl having 1 to 5 halogen atoms, C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₁-C₄-alkylamino, di-(C₁-C₄-alkyl)amino, C₁-C₄-alkoxy, C₁-C₄-halogenoalkoxy having 1 to 5 halogen atoms, C₂-C₄-alkenyloxy, C₂-C₄-halogenoalkenyloxy having 1 to 5 halogen atoms, C₃-C₄-alkynyloxy, C₃-C₄-halogenoalkynyloxy having 1 to 5 halogen atoms, C₃-C₆-cycloalkyl, C₃-C₆-halogenocycloalkyl having 1 to 5 halogen atoms, C₁-C₄-alkylcarbonyl, C₁-C₄-halogenoalkylcarbonyl having 1 to 5 halogen atoms, —CONH(C₁-C₄-alkyl), —CON(C₁-C₄-alkyl)₂, —CONH(OC₁-C₄-alkyl), —CON(OC₁-C₄-alkyl)(C₁-C₄-alkyl), C₁-C₄-alkoxycarbonyl, C₁-C₄-halogenoalkoxycarbonyl having 1 to 5 halogen atoms, C₁-C₄-alkylcarbonyloxy, C₁-C₄-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, C₁-C₄-alkylcarbonylamino, C₁-C₄-halogenoalkylcarbonylamino having 1 to 5 halogen atoms, —OCONH(C₁-C₄-alkyl), —OCON(C₁-C₄-alkyl)₂, —OCONH(OC₁-C₄-alkyl), —OCO(OC₁-C₄-alkyl), —S—C₁-C₄-alkyl, —S—C₁-C₄-halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C₁-C₄-alkyl, —S(O)—C₁-C₄-halogenoalkyl having 1 to 5 halogen atoms, —S(O)₂—C₁-C₄-alkyl, —S(O)₂—C₁-C₄-halogenoalkyl having 1 to 5 halogen atoms, (C₁-C₄-alkoxyimino)-C₁-C₄-alkyl, (C₂-C₆-alkenyloxyimino)-C₁-C₄-alkyl, (C₃-C₆-alkynyloxyimino)-C₁-C₄-alkyl, (benzyloxyimino)-C₁-C₆-alkyl, benzyloxy, —S-benzyl, benzylamino, phenoxy, —S-phenyl and phenylamino,
n is 1, 2, 3 or 4 and if n is 2, 3, or 4 then the substituents X may be the same or different.
R¹and R²are the same or different and are selected from the group consisting of hydrogen, halogen, cyano, hydroxy, amino, —CHO, —OCHO, —NHCHO, —COOH, —CONH₂, C₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₁-C₄-alkylamino, di-(C₁-C₄-alkyl)amino, C₁-C₄-alkoxy, C₁-C₄-halogenoalkyl having 1 to 5 halogen atoms, C₁-C₄-halogenoalkoxy having 1 to 5 halogen atoms, C₂-C₄-alkenyloxy, C₂-C₄-halogenoalkenyloxy having 1 to 5 halogen atoms, C₃-C₄-alkynyloxy, C₃-C₄-halogenoalkynyloxy having 1 to 5 halogen atoms, C₃-C₆-cycloalkyl, C₃-C₆-halogenocycloalkyl having 1 to 5 halogen atoms, C₃-C₆-cycloalkyl-C₁-C₃-alkyl, C₃-C₆-halogenocycloalkyl-C₁-C₃-alkyl having 1 to 5 halogen atoms, C₁-C₄-alkylcarbonyl, C₁-C₄-halogenoalkylcarbonyl having 1 to 5 halogen atoms, —CONH(C₁-C₄-alkyl), —CON(C₁-C₄-alkyl)₂, —CONH(OC₁-C₄-alkyl), —CON(OC₁-C₄-alkyl)(C₁-C₄-alkyl), C₁-C₄-alkoxycarbonyl, C₁-C₄-halogenoalkoxycarbonyl having 1 to 5 halogen atoms, —OC(O)—C₁-C₄-alkyl, —OC(O)—C₁-C₄-halogenoalkyl having 1 to 5 halogen atoms, —NHC(O)—C₁-C₄-alkyl, —NHC(O)—C₁-C₄-halogenoalkyl having 1 to 5 halogen atoms, —OCONH(C₁-C₄-alkyl), —OCON(C₁-C₄-alkyl)₂, —OCONH(OC₁-C₄-alkyl), OCO(OC₁-C₄-alkyl), —S—C₁-C₄-alkyl, —S—C₁-C₄-halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C₁-C₄-alkyl, —S(O)—C₁-C₄-halogenoalkyl having 1 to 5 halogen atoms, —S(O)₂—C₁-C₄-alkyl, —S(O)₂—C₁-C₄-halogenoalkyl having 1 to 5 halogen atoms, benzyl, benzyloxy, —S-benzyl, —S(O)-benzyl, —S(O)₂-benzyl, benzylamino, phenoxy, —S-phenyl, —S(O)-phenyl, —S(O)₂-phenyl, phenylamino, phenylcarbonylamino, 2,6-dichlorophenyl-carbonylamino, 2-chlorophenyl-carbonylamino and phenyl or
- R¹and R²together with the carbon atom to which they are bonded form a 3-, 5- or 6-membered carbocycle,
R³and R⁴are the same or different and are selected from the group consisting of hydrogen, halogen, cyano, hydroxy, amino, —CHO, —COOH, —CONH₂, C₁-C₄alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₁-C₄-alkylamino, di-(C₁-C₄-alkyl)amino, C₁-C₄-alkoxy, hydroxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₃-alkyl, C₁-C₄-halogenoalkyl having 1 to 5 halogen atoms, C₁-C₄-halogenoalkoxy having 1 to 5 halogen atoms, C₂-C₄-alkenyloxy, C₂-C₄-halogenoalkenyloxy having 1 to 5 halogen atoms, C₃-C₄-alkynyloxy, C₃-C₄-halogenoalkynyloxy having 1 to 5 halogen atoms, C₃-C₆-cycloalkyl, C₃-C₆-halogenocycloalkyl having 1 to 5 halogen atoms, C₁-C₄-alkylcarbonyl, C₁-C₄-halogenoalkylcarbonyl having 1 to 5 halogen atoms, —CONH(C₁-C₄-alkyl), —CON(C₁-C₄-alkyl)₂, —CONH(OC₁-C₄-alkyl), —CON(OC₁-C₄-alkyl)(C₁-C₄-alkyl), C₁-C₄-alkoxycarbonyl, C₁-C₄-halogenoalkoxycarbonyl having 1 to 5 halogen atoms, —OC(O)—C₁-C₄-alkyl, —OC(O)—C₁-C₄-halogenoalkyl having 1 to 5 halogen atoms, —NHC(O)—C₁-C₄-alkyl, —NHC(O)—C₁-C₄-halogenoalkyl having 1 to 5 halogen atoms, —OCONH(C₁-C₄-alkyl), —OCON(C₁-C₄-alkyl)₂, —OCONH(OC₁-C₄-alkyl), OCO(OC₁-C₄-alkyl), —S—C₁-C₄-alkyl, —S—C₁-C₄-halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C₁-C₄-alkyl, —S(O)—C₁-C₄-halogenoalkyl having 1 to 5 halogen atoms, —S(O)₂—C₁-C₄-alkyl, —S(O)₂—C₁-C₄-halogenoalkyl having 1 to 5 halogen atoms, benzyl, benzyloxy, —S-benzyl, —S(O)-benzyl, —S(O)₂-benzyl, benzylamino, phenoxy, —S-phenyl, —S(O)-phenyl, —S(O)₂-phenyl, phenylamino, phenylcarbonylamino, 2-chlorophenyl-carbonylamino, 2,6-dichlorophenyl-carbonylamino and phenyl;
R⁵is selected from the group consisting of hydrogen, —CHO, —OH, C₁-C₄-alkyl, C₁-C₄-halogenoalkyl having 1 to 5 halogen atoms, C₁-C₄-alkoxy, C₁-C₄-halogenoalkoxy having 1 to 5 halogen atoms, C₃-C₆-cycloalkyl, C₃-C₆-halogenocycloalkyl having 1 to 5 halogen atoms, C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₃-C₆-cycloalkyl-C₁-C₃-alkyl, cyano-C₁-C₄-alkyl, amino-C₁-C₄-alkyl, C₁-C₄-alkylamino-C₁-C₄-alkyl, di-(C₁-C₄-alkyl)amino-C₁-C₄-alkyl, C₁-C₄-alkylcarbonyl, C₁-C₄-halogenoalkylcarbonyl having 1 to 5 halogen atoms, C₁-C₄-alkoxycarbonyl, benzyloxycarbonyl, C₁-C₄-alkoxy-C₁-C₄-alkylcarbonyl, —S(O)₂—C₁-C₄-alkyl, and —S(O)₂—C₁-C₄-halogenoalkyl having 1 to 5 halogen atoms;
A represents a phenyl group of formula (A1)

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wherein

R is selected from the group consisting of halogen, nitro, —OH, CHO, OCHO, NHCHO, cyano, C₁-C₄-alkyl, C₁-C₄-halogenoalkyl having 1 to 5 halogen atoms, C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₃-C₆-cycloalkyl, —S—C₁-C₄-alkyl, —S—C₁-C₄-halogenoalkyl having 1 to 5 halogen atoms, C₁-C₄-alkoxy, C₁-C₄-halogenoalkoxy having 1 to 5 halogen atoms, C₁-C₄-alkoxy-C₂-C₄-alkenyl, C₁-C₄-alkoxycarbonyl, C₁-C₄-halogenoalkoxycarbonyl having 1 to 5 halogen atoms, C₁-C₄-alkylcarbonyloxy, C₁-C₄-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, —S(O)—C₁-C₄-alkyl, —S(O)—C₁-C₄-halogenoalkyl having 1 to 5 halogen atoms, —S(O)₂—C₁-C₄-alkyl, —S(O)₂—C₁-C₄-halogenoalkyl having 1 to 5 halogen atoms, C₁-C₄-alkylsulfonamide, —NH(C₁-C₄-alkyl), N(C₁-C₄-alkyl)₂, phenyl (optionally substituted by C₁-C₄-alkoxy) and phenoxy, or two R bonded to adjacent carbon atoms together represent —O(CH₂)_pO—, wherein p represents 1 or 2,
m is 0, 1, 2, 3, 4 or 5 and if m is 2, 3, 4, or 5 then the substituents R may be the same or different.

In compounds of formula (I), the use of which is particularly preferred, R, R¹, R², R³, R⁴, R⁵X, B, n and m have the following meanings.

B represents 2-pyridyl, 3-pyridyl, or 4-pyridyl.
X is selected from the group consisting of halogen C₁-C₄-alkyl, C₁-C₄-halogenoalkyl having 1 to 5 halogen atoms, C₁-C₄-alkoxy.
n is 1, 2, 3 or 4 and if n is 2, 3, or 4 then the substituents X may be the same or different.
R¹and R²are the same or different and are selected from the group consisting of hydrogen, halogen, cyano, hydroxy, C₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₁-C₄-alkoxy, C₃-C₆-cycloalkyl-C₁-C₃-alkyl, C₁-C₄-alkoxycarbonyl, —OC(O)—C₁-C₄-alkyl, —NHC(O)—C₁-C₄-alkyl, 2,6-dichlorophenyl-carbonylamino, 2-chlorophenyl-carbonylamino and phenyl or R¹and R²together with the carbon atom to which they are bonded form a 3- or 5-membered carbocycle.
R³and R⁴are the same or different and are selected from the group consisting of hydrogen, —COOH, C₁-C₄-alkyl, C₁-C₄-halogenoalkyl C₁-C₄-alkoxy, hydroxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₃-alkyl, —CONH(C₁-C₄-alkyl), C₁-C₄-alkoxycarbonyl, —OC(O)—C₁-C₄-alkyl, and phenyl.
R⁵is selected from the group consisting of hydrogen, C₃-C₆-cycloalkyl, C₁-C₄-alkylcarbonyl, and C₁-C₄-alkoxycarbonyl.

A represents a phenyl group of formula (A1)

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wherein

R is selected from the group consisting of halogen, nitro, —OH, cyano, C₁-C₄-alkyl, C₁-C₄-halogenoalkyl having 1 to 5 halogen atoms, C₃-C₆-cycloalkyl, C₁-C₄-alkoxy, C₁-C₁-C₄-alkoxycarbonyl, —NH(C₁-C₄-alkyl), phenyl (optionally substituted by C₁-C₄-alkoxy) and phenoxy.
m is 0, 1, 2 or 3 and if m is 2 or 3 then the substituents R may be the same or different.

The provisos mentioned above apply also with regard to the preferred and particularly preferred definitions.

A “nematicide” as used herein means that the compound is capable of controlling nematodes.

“Controlling nematodes” as used in the present invention means killing nematodes or preventing nematodes to develop or to grow. Controlling nematodes as used herein also encompasses controlling nematode progeny (development of viable cysts and/or egg masses). The compounds described herein, may be used to keep an organism healthy and may be used curatively, pre-emptively or systematically to control nematodes.

The “organism” as mentioned in the above paragraphs may be a plant. When using the compounds described herein, to keep a plant healthy, the controlling of nematodes as used herein encompasses the reduction of damage to plants and/or encompasses increased yield.

Alternatively, the organisms as mentioned above may be a human or an animal. When using the compounds described herein to keep a human or animal healthy, the use encompasses therapeutic use and veterinarian use with the aim to prevent or to cure damage by nematodes.

“Nematodes” as used herein encompass all species of the order Nematoda and in particular species that are parasitic or cause health problems to plants or to fungi (for example species of the orders Aphelenchida, Meloidogyne, Tylenchida and others) or to humans and animals (for example species of the orders Ascaradida, Oxyurida, Strongylida, Stronglyloides and Trichocephalida).

Preferably, “nematodes” as used herein, refer to plant nematodes meaning plant parasitic nematodes that cause damage to plants. Plant nematodes encompass plant parasitic nematodes and nematodes living in the soil. Plant parasitic nematodes include, but are not limited to, ectoparasites such as Xiphinema spp., Longidorus spp., and Trichodorus spp.; semiparasites such as Tylenchulus spp.; migratory endoparasites such as Pratylenchus spp., Radopholus spp., and Scutellonerna spp.; sedentary parasites such as Heterodera spp., Globoderal spp., and Meloidogyne spp., and stem and leaf endoparasites such as Ditylenchus spp., Aphelenchoides spp., and Hirshmaniella spp. The compounds described herein are distinguished especially for their effective control of halmful root parasitic soil nematodes such as, cystforming nematodes of the genera Heterodera or Globodera, and/or root knot nematodes of the genus Meloidogyne. Harmful species of these genera are for example Meloidogyne incognata, Heterodera glycines (soybean cyst nematode), Globodera pallida and Globodera rostochiensis (potato cyst nematode), which species are effectively controlled with the compounds described herein. However, the use of the compounds described herein is in no way restricted to these genera or species, but also extends in the same manner to other nematodes.

The compounds described herein may have a broad spectrum activity against various genera and/or strains and/or species of nematodes including but not limited to e.g. Aglenchus agricola, Anguina tritici, Aphelenchoides arachidis, Aphelenchoides fragaria and the stem and leaf endoparasites Aphelenchoides spp. in general, Belonolaimus gracilis, Belonolaimus longicaudatus, Belonolaimus nortoni, Bursaphelenchus eremus, Bursaphelenchus xylophilus and Bursaphelenchus spp. in general, Cacopaurus pestis, Criconemella curvata, Criconemella onoensis, Criconemella ornata, Criconemella rusium, Criconemella xenoplax (=Mesocriconema xenoplax) and Criconemella spp. in general, Criconemoides ferniae, Criconemoides onoense, Criconemoides ornatum and Criconemoides spp. in general, Ditylenchus destructor, Ditylenchus dipsaci, Ditylenchus myceliophagus and the stem and leaf endoparasites Ditylenchus spp. in general, Dolichodorus heterocephalus, Globodera pallida (=Heterodera pallida), Globodera rostochiensis (potato cyst nematode), Globodera solanacearum, Globodera tabacum, Globodera Virginia and the sedentary, cyst forming parasites Globodera spp. in general Helicotylenchus digonicus, Helicotylenchus dihystera, Helicotylenchus erythrine, Helicotylenchus multicinctus, Helicotylenchus nannus, Helicotylenchus pseudorobustus and Helicotylenchus spp. in general, Hemicriconemoides, Hemicycliophora arenaria, Hemicycliophora nudata, Hemicycliophora parvana, Heterodera avenae, Heterodera cruciferae, Heterodera glycines (soybean cyst nematode), Heterodera oryzae, Heterodera schachtii, Heterodera zeae and the sedentary, cyst forming parasites Heterodera spp. in general, Hirschmaniella gracilis, Hirschmaniella oryzae Hirschmaniella spinicaudata and the stem and leaf endoparasites Hirschmaniella spp. in general, Hoplolaimus aegyptii, Hoplolaimus californicus, Hoplolaimus columbus, Hoplolaimus galeatus, Hoplolaimus indicus, Hoplolaimus magnistylus, Hoplolaimus pararobustus, Longidorus africanus, Longidorus breviannulatus, Longidorus elongatus, Longidorus laevicapitatus, Longidorus vineacola and the ectoparasites Longidorus spp. in general, Meloidogyne acronea, Meloidogyne africana, Meloidogyne arenaria, Meloidogyne arenaria thamesi, Meloidogyne artiella, Meloidogyne chitwoodi, Meloidogyne coffeicola, Meloidogyne ethiopica, Meloidogyne exigua, Meloidogyne graminicola, Meloidogyne graminis, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne incognita acrita, Meloidogyne javanica, Meloidogyne kikuyensis, Meloidogyne naasi, Meloidogyne paranaensis, Meloidogyne thamesi and the sedentary parasites Meloidogyne spp. in general, Meloinema spp., Nacobbus aberrans, Neotylenchus vigissi, Paraphelenchus pseudoparietinus, Paratrichodorus allius, Paratrichodorus lobatus, Paratrichodorus minor, Paratrichodorus nanus, Paratrichodorus porosus, Paratrichodorus teres and Paratrichodorus spp. in general, Paratylenchus hamatus, Paratylenchus minutus, Paratylenchus projectus and Paratylenchus spp. in general, Pratylenchus agilis, Pratylenchus alleni, Pratylenchus andinus, Pratylenchus brachyurus, Pratylenchus cerealis, Pratylenchus coffeae, Pratylenchus crenatus, Pratylenchus delattrei, Pratylenchus giibbicaudatus, Pratylenchus goodeyi, Pratylenchus hamatus, Pratylenchus hexincisus, Pratylenchus loosi, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus pratensis, Pratylenchus scribneri, Pratylenchus teres, Pratylenchus thornei, Pratylenchus vulnus, Pratylenchus zeae and the migratory endoparasites Pratylenchus spp. in general, Pseudohalenchus minutus, Psilenchus magnidens, Psilenchus tumidus, Punctodera chalcoensis, Quinisulcius acutus, Radopholus citrophilus, Radopholus similis, the migratory endoparasites Radopholus spp. in general, Rotylenchulus borealis, Rotylenchulus parvus, Rotylenchulus reniformis and Rotylenchulus spp. in general, Rotylenchus laurentinus, Rotylenchus macrodoratus, Rotylenchus robustus, Rotylenchus uniformis and Rotylenchus spp. in general, Scutellonema brachyurum, Scutellonema bradys, Scutellonema clathricaudatum and the migratory endoparasites Scutellonema spp. in general, Subanguina radiciola, Tetylenchus nicotianae, Trichodorus cylindricus, Trichodorus minor, Trichodorus primitivus, Trichodorus proximus, Trichodorus similis, Trichodorus sparsus and the ectoparasites Trichodorus spp. in general, Tylenchorhynchus agri, Tylenchorhynchus brassicae, Tylenchorhynchus clarus, Tylenchorhynchus claytoni, Tylenchorhynchus digitatus, Tylenchorhynchus ebriensis, Tylenchorhynchus maximus, Tylenchorhynchus nudus, Tylenchorhynchus vulgaris and Tylenchorhynchus spp. in general, Tylenchulus semipenetrans and the semiparasites Tylenchulus spp. in general, Xiphinema americanum, Xiphinema brevicolle, Xiphinema

Nematicides comprising as an active ingredient a compound of formula (I) are suitable for the control of nematodes in soil in the fields of fruit trees, vegetables, other crops and ornamental plants.

Examples of nematodes to which a nematicide of the present invention is applicable include, but are not limited to, nematodes of the genus Meloidogyne such as the southern root-knot nematode (Meloidogyne incognita), Javanese root-knot nematode (Meloidogyne javanica), northern root-knot nematode (Meloidogyne hapla), and peanut root-knot nematode (Meloidogyne arenaria); nematodes of the genus Ditylenchus such as the potato rot nematode (Ditylenchus destructor) and bulb and stem nematode (Ditylenchus dipsaci); nematodes of the genus Pratylenchus such as the cob root-lesion nematode (Pratylenchus penetrans), chrysanthemum root-lesion nematode (Pratylenchus fallax), coffee root-lesion nematode (Pratylenchus coffeae), tea root-lesion nematode (Pratylenchus loosi), and walnut root-lesion nematode (Pratylenchus vulnus); nematodes of the genus Globodera such as the golden nematode (Globodera rostochiensis) and potato cyst nematode (Globodera pallida); nematodes of the genus Heterodera such as the soybean cyst nematode (Heterodera glycines) and sugar beet cyst nematode (Heterodera schachtii); nematodes of the genus Aphelenchoides such as the rice white-tip nematode (Aphelenchoides besseyi), chrysanthemum foliar nematode (Aphelenchoides ritzemabosi), and strawberry nematode (Aphelenchoides fragariae); nematodes of the genus Aphelenchus such as the mycophagous nematode (Aphelenchus avenae); nematodes of the genus Radopholus such as the burrowing nematode (Radopholus similis); nematodes of the genus Tylenchulus such as the citrus nematode (Tylenchulus semipenetrans); nematodes of the genus Rotylenchulus such as the reniform nematode (Rotylenchulus reniformis); nematodes that occur in trees, such as the pine wood nematode (Bursaphelenchus xylophilus), and the like. Furthermore, a nematocidal composition of the present invention is also effective against animal parasitic nematodes such as ascarid, oxyurid, anisakis, filaria, Wuchereria bancrofti, Onchocerca volvulus, and Gnathostoma.

Plants for which a nematicide of the present invention can be used are not particularly limited; for example, plants such as cereals (for example, rice, barley, wheat, rye, oat, corn, kaoliang 5 and the like), beans (soybean, azuki, bean, broad bean, peas, peanuts and the like), fruit trees/fruits (apples, citruses, pears, grapes, peaches, Japanese apricots, cherries, walnuts, almonds, bananas, strawberries and the like), vegetables (cabbage, tomato, spinach, broccoli, lettuce, onion, Welsh onion, pepper and the like), root crops (carrot, potato, sweet potato, radish, lotus root, turnip and the like), industrial crops (cotton, hemp, paper mulberry, mitsumata, rape, beet, hop, sugarcane, sugar beet, olive, rubber, coffee, tobacco, tea and the like), pepos (pumpkin, cucumber, watermelon, melon and the like), pasture plants (orchard grass, sorghum, thimosy, clover, alfalfa and the like), lawn grasses (mascarene grass, bent grass and the like), crops for flavorings etc. (lavender, rosemary, thyme, parsley, pepper, ginger and the like), and flower plants (chrysanthemum, rose, orchids and the like) can be mentioned.

Alternatively, “nematodes” as used herein, refer to nematodes which cause damage to humans or animals.

Specific nematode species harmful to humans or animals are Ascaris suum, Trichinella spiralis, Trichuris suis (pig), Ascaris lumbricoides, Trichinella sp. (human), Ostertagia ostertagi, Haemonchus placei, Cooperia oncophora, Dictyocaulus viviparus, Fasciola hepatica (cattle), Haemonchus contortus, Nematodirus battus (sheep), Strongyloides sp. (horse), Ancylostoma caninum, Toxocara canis (dog), Toxocara cati, Taenia taeniaeformis (cat). Moreover, many known nematicides are equally active as anthelmintic and are used to control human and animal parasitic worms, which do not necessarily belong to the group of nematoda. Therefore, it is envisaged by the present invention that the compounds described herein may also be used as anthelmintic.

A further aspect of the invention are nematicidal compositions, comprising an effective amount of at least one compound as defined herein and at least one of the following: surfactant, solid or liquid diluent, characterized in that the surfactant or the diluent is normally used in nematicidal compositions. In an embodiment, said composition comprises at least two compounds as defined herein.

A related aspect of the invention is a method for preparing a nematicidal composition as described herein, comprising the step of mixing at least one compound as described herein with a surfactant or diluent normally used in nematicidal compositions. In an embodiment, said method comprises mixing least two compounds as defined herein with a surfactant or diluent normally used in nematicidal compositions.

In particular, the present invention relates to nematicidal composition developed to be used in agriculture or horticulture. These nematicidal compositions may be prepared in a manner known per se. The present invention further provides formulations, and application forms prepared from them, as crop protection agents and/or pesticidal agents, such as drench, drip and spray liquors, comprising at least one of the active compounds of the invention. The application forms may comprise further crop protection agents and/or pesticidal agents, and/or activity-enhancing adjuvants such as penetrants, examples being vegetable oils such as, for example, rapeseed oil, sunflower oil, mineral oils such as, for example, liquid paraffins, alkyl esters of vegetable fatty acids, such as rapeseed oil or soybean oil methyl esters, or alkanol alkoxylates, and/or spreaders such as, for example, alkylsiloxanes and/or salts, examples being organic or inorganic ammonium or phosphonium salts, examples being ammonium sulphate or diammonium hydrogen phosphate, and/or retention promoters such as dioctyl sulphosuccinate or hydroxypropylguar polymers and/or humectants such as glycerol and/or fertilizers such as ammonium, potassium or phosphorous fertilizers, for example.

Examples of typical formulations include water-soluble liquids (SL), emulsifiable concentrates (EC), emulsions in water (EW), suspension concentrates (SC, SE, FS, OD), water-dispersible granules (WG), granules (GR) and capsule concentrates (CS); these and other possible types of formulation are described, for example, by Crop Life International and in Pesticide Specifications, Manual on development and use of FAO and WHO specifications for pesticides, FAO Plant Production and Protection Papers—173, prepared by the FAO/WHO Joint Meeting on Pesticide Specifications, 2004, ISBN: 9251048576. The formulations may comprise active agrochemical compounds other than one or more active compounds of the invention.

The formulations or application forms in question preferably comprise auxiliaries, such as extenders, solvents, spontaneity promoters, carriers, emulsifiers, dispersants, frost protectants, biocides, thickeners and/or other auxiliaries, such as adjuvants, for example. An adjuvant in this context is a component which enhances the biological effect of the formulation, without the component itself having a biological effect. Examples of adjuvants are agents which promote the retention, spreading, attachment to the leaf surface, or penetration.

These formulations are produced in a known manner, for example by mixing the active compounds with auxiliaries such as, for example, extenders, solvents and/or solid carriers and/or further auxiliaries, such as, for example, surfactants. The formulations are prepared either in suitable plants or else before or during the application.

Suitable for use as auxiliaries are substances which are suitable for imparting to the formulation of the active compound or the application forms prepared from these formulations (such as, e.g., usable crop protection agents, such as spray liquors or seed dressings) particular properties such as certain physical, technical and/or biological properties.

Suitable extenders are, for example, water, polar and nonpolar organic chemical liquids, for example from the classes of the aromatic and non-aromatic hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), the alcohols and polyols (which, if appropriate, may also be substituted, etherified and/or esterified), the ketones (such as acetone, cyclohexanone), esters (including fats and oils) and (poly)ethers, the unsubstituted and substituted amines, amides, lactams (such as Nalkylpyrrolidones) and lactones, the sulphones and sulphoxides (such as dimethyl sulphoxide).

If the extender used is water, it is also possible to employ, for example, organic solvents as auxiliary solvents. Essentially, suitable liquid solvents are: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol and also their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulphoxide, and also water.

In principle it is possible to use all suitable solvents. Suitable solvents are, for example, aromatic hydrocarbons, such as xylene, toluene or alkylnaphthalenes, for example, chlorinated aromatic or aliphatic hydrocarbons, such as chlorobenzene, chloroethylene or methylene chloride, for example, aliphatic hydrocarbons, such as cyclohexane, for example, paraffins, petroleum fractions, mineral and vegetable oils, alcohols, such as methanol, ethanol, isopropanol, butanol or glycol, for example, and also their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, for example, strongly polar solvents, such as dimethyl sulphoxide, and water.

All suitable carriers may in principle be used. Suitable carriers are in particular: for example, ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica, alumina and natural or synthetic silicates, resins, waxes and/or solid fertilizers. Mixtures of such carriers may likewise be used. Carriers suitable for granules include the following: for example, crushed and fractionated natural minerals such as calcite, marble, pumice, sepiolite, dolomite, and also synthetic granules of inorganic and organic meals, and also granules of organic material such as sawdust, paper, coconut shells, maize cobs and tobacco stalks.

Liquefied gaseous extenders or solvents may also be used. Particularly suitable are those extenders or carriers which at standard temperature and under standard pressure are gaseous, examples being aerosol propellants, such as halogenated hydrocarbons, and also butane, propane, nitrogen and carbon dioxide. Examples of emulsifiers and/or foam-formers, dispersants or wetting agents having ionic or nonionic properties, or mixtures of these surface-active substances, are salts of polyacrylic acid, salts of lignosulphonic acid, salts of phenolsulphonic acid or naphthalenesulphonic acid, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, with substituted phenols (preferably alkylphenols or arylphenols), salts of sulphosuccinic esters, taurine derivatives 5 (preferably alkyltaurates), phosphoric esters of polyethoxylated alcohols or phenols, fatty acid esters of polyols, and derivatives of the compounds containing sulphates, sulphonates and phosphates, examples being Alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates, protein hydrolysates, lignin-sulphite waste liquors and methylcellulose. The presence of a surface-active substance is advantageous if one of the active compounds and/or one of the inert carriers is not soluble in water and if application takes place in water.

Further auxiliaries that may be present in the formulations and in the application forms derived from them include colorants such as inorganic pigments, examples being iron oxide, titanium oxide, Prussian Blue, and organic dyes, such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and nutrients and trace nutrients, such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

Stabilizers, such as low-temperature stabilizers, preservatives, antioxidants, light stabilizers or other agents which improve chemical and/or physical stability may also be present. Additionally present may be foam-formers or defoamers.

Furthermore, the formulations and application forms derived from them may also comprise, as additional auxiliaries, stickers such as carboxymethylcellulose, natural and synthetic polymers in powder, granule or latex form, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and also natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids. Further possible auxiliaries include mineral and vegetable oils.

There may possibly be further auxiliaries present in the formulations and the application forms derived from them. Examples of such additives include fragrances, protective colloids, binders, adhesives, thickeners, thixotropic substances, penetrants, retention promoters, stabilizers, sequestrants, complexing agents, humectants and spreaders. Generally speaking, the active compounds may be combined with any solid or liquid additive commonly used for formulation purposes.

Suitable retention promoters include all those substances which reduce the dynamic surface tension, such as dioctyl sulphosuccinate, or increase the viscoelasticity, such as hydroxypropylguar polymers, for example.

Suitable penetrants in the present context include all those substances which are typically used in order to enhance the penetration of active agrochemical compounds into plants. Penetrants in this context are defined in that, from the (generally aqueous) application liquor and/or from the spray coating, they areable to penetrate the cuticle of the plant and thereby increase the mobility of the active compounds in thecuticle. This property can be determined using the method described in the literature (Baur et al., 1997, Pesticide Science 51, 131-152). Examples include alcohol alkoxylates such as coconut fatty ethoxylate (10) or isotridecyl ethoxylate (12), fatty acid esters such as rapeseed or soybean oil methyl esters, fatty amine alkoxylates such as tallowamine ethoxylate (15), or ammonium and/or phosphonium salts such as ammonium sulphate or diammonium hydrogen phosphate, for example.

The formulations preferably comprise between 0.00000001% and 98% by weight of active compound or, with particular preference, between 0.01% and 95% by weight of active compound, more preferably between 0.5% and 90% by weight of active compound, based on the weight of the formulation.

The active compound content of the application forms (crop protection products) prepared from the formulations may vary within wide ranges. The active compound concentration of the application forms may be situated typically between 0.00000001% and 95% by weight of active compound, preferably between 0.00001% and 1% by weight, based on the weight of the application form. Application takes place in a customary manner adapted to the application forms.

The compounds are applied in a customary manner appropriate for the use forms.

All plants and plant parts can be treated in accordance with the invention. Plants are understood here to mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants may be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant varieties which are protectable and non-protectable by plant breeders' rights. Parts of plants shall be understood to mean all above-ground and below-ground parts and organs of plants, such as shoot, leaf, flower and root, examples including leaves, needles, stems, trunks, flowers, fruit bodies, fruits and seeds, and also roots, tubers and rhizomes. The plant parts also include harvested material and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, slips and seeds.

The inventive treatment of the plants and plant parts with the active ingredients is effected directly or by allowing them to act on the surroundings, habitat or storage space thereof by the customary treatment methods, for example by dipping, spraying, evaporating, fogging, scattering, painting on, injecting, and, in the case of propagation material, especially in the case of seeds, also by applying one or more coats.

As already mentioned above, it is possible to treat all plants and their parts in accordance with the invention. In a preferred embodiment, wild plant species and plant cultivars, or those obtained by conventional biological breeding methods, such as crossing or protoplast fusion, and also parts thereof, are treated. In a further preferred embodiment, transgenic plants and plant cultivars obtained by genetic engineering, if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated. The terms “parts” or “parts of plants” or “plant parts” have been explained above.

More preferably, plants of the plant cultivars which are each commercially available or in use are treated in accordance with the invention. Plant cultivars are understood to mean plants having new properties (“traits”) and which have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. They may be cultivars, biotypes and genotypes.

Depending on the plant species or plant cultivars, and the location and growth conditions (soils, climate, vegetation period, diet) thereof, the inventive treatment may also result in superadditive (“synergistic”) effects. For example, possibilities include reduced application rates and/or broadening of the activity spectrum and/or an increase in the activity of the compounds and compositions usable in accordance with the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to levels of water or soil salinity, enhanced flowering performance, easier harvesting, accelerated ripening, higher yields, higher quality and/or higher nutritional value of the harvested products, increased storage life and/or processibility of the harvested products, which exceed the effects normally to be expected.

The transgenic plants or plant cultivars (those obtained by genetic engineering) which are to be treated with preference in accordance with the invention include all plants which, through the genetic modification, received genetic material which imparts particular advantageous useful properties (“traits”) to these plants. Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to levels of water or soil salinity, enhanced flowering performance, easier harvesting, accelerated ripening, higher yields, higher quality and/or a higher nutritional value of the harvested products, better storage life and/or processibility of the harvested products. Further and particularly emphasized examples of such properties are an improved defence of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and/or viruses, and also increased tolerance of the plants to certain herbicidally active ingredients. Examples of transgenic plants include the important crop plants, such as cereals (wheat, rice), maize, soya, potatoes, sugar beet, tomatoes, peas and other vegetable types, cotton, tobacco, oilseed rape, and also fruit plants (with the fruits of apples, pears, citrus fruits and grapes), particular emphasis being given to maize, soya, potatoes, cotton, tobacco and oilseed rape. Traits that are particularly emphasized are improved defence of the plants against insects, arachnids, nematodes, slugs and snails by toxins formed in the plants, especially those formed in the plants by the genetic material from Bacillus thuringiensis (for example by the genes CryIA(a), CryIA(b), CryIA(c), CryIIA, CryIIIA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CryIF, and also combinations thereof) (referred to hereinafter as “Bt plants”). Traits that are also particularly emphasized are the improved defence of plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), systemn, phytoalexins, elicitors and also resistance genes and correspondingly expressed proteins and toxins. Traits that are additionally particularly emphasized are the increased tolerance of the plants to certain active herbicidal ingredients, for example imidazolinones, sulphonylureas, glyphosate or phosphinothricin (for example the “PAT” gene). The genes which impart the desired traits in question may also be present in combinations with one another in the transgenic plants. Examples of “Bt plants” include maize varieties, cotton varieties, soya varieties and potato varieties which are sold under the trade names YIELD GARD® (for example maize, cotton, soya), KnockOut® (for example maize), StarLink® (for example maize), Bollgard® (cotton), Nucotn® (cotton) and NewLeaf® (potato). Examples of herbicide-tolerant plants include maize varieties, cotton varieties and soya varieties which are sold under the trade names Roundup Ready® (tolerance to glyphosate, for example maize, cotton, soya), Liberty Link® (tolerance to phosphinothricin, for example oilseed rape), IMI® (tolerance to imidazolinones) and STS (tolerance to sulphonylureas, for example maize) Herbicide-resistant plants (plants bred in a conventional manner for herbicide tolerance) which may be mentioned include the varieties sold under the name Clearfield® (for example maize) Of course, these statements also apply to plant cultivars which have these genetic traits or genetic traits which are still to be developed and will be developed and/or marketed in the future.

The plants listed can be treated in accordance with the invention in a particularly advantageous manner with the compounds of the general formula (I) and/or the active ingredient mixtures according to the invention. The preferred ranges stated above for the active ingredients or mixtures also apply to the treatment of these plants. Particular emphasis is given to the treatment of plants with the compounds or mixtures specifically mentioned in the present text.

The inventive active ingredient may be present in its commercially available formulations and in the use forms, prepared from these formulations, as a mixture with other active ingredients, such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators, herbicides, safeners, fertilizers or semiochemicals. The mixtures thus obtained have a broadened spectrum of activity.

Mixtures with fungicides are particularly advantageous. Examples of suitable fungicide mixing partners can be selected from the list consisting of

(1) Inhibitors of the ergosterol biosynthesis, for example aldimorph, azaconazole, bitertanol, bromuconazole, cyproconazole, diclobutrazole, difenoconazole, diniconazole, diniconazole-M, dodemorph, dodemorph acetate, epoxiconazole, etaconazole, fenarimol, fenbuconazole, fenhexamid, fenpropidin, fenpropimorph, fluquinconazole, flurprimidol, flusilazole, flutriafol, furconazole, furconazole-cis, hexaconazole, imazalil, imazalil sulfate, imibenconazole, ipconazole, metconazole, myclobutanil, naftifine, nuarimol, oxpoconazole, paclobutrazol, pefurazoate, penconazole, piperalin, prochloraz, propiconazole, prothioconazole, pyributicarb, pyrifenox, quinconazole, simeconazole, spiroxamine, tebuconazole, terbinafine, tetraconazole, triadimefon, triadimenol, tridemorph, triflumizole, triforine, triticonazole, uniconazole, uniconazole-p, viniconazole, voriconazole, 1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)cycloheptanol, methyl 1-(2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)-1H-imidazole-5-carboxylate, N′-{5-(difluoromethyl)-2-methyl-4-[3-(trimethylsilyl)propoxy]phenyl}-N-ethyl-N-methylimidoformamide, N-ethyl-N-methyl-N′-{2-methyl-5-(trifluoromethyl)-4-[3-(trimethylsilyl)propoxy]phenyl}imidoformamide and O-[1-(4-methoxyphenoxy)-3,3-dimethylbutan-2-yl] 1H-imidazole-1-carbothioate.

(2) inhibitors of the respiratory chain at complex I or II, for example bixafen, boscalid, carboxin, diflumetorim, fenfuram, fluopyram, flutolanil, fluxapyroxad, furametpyr, furmecyclox, isopyrazam (mixture of syn-epimeric racemate 1RS,4SR,9RS and anti-epimeric racemate 1RS,4SR,9SR), isopyrazam (anti-epimeric racemate 1RS,4SR,9SR), isopyrazam (anti-epimeric enantiomer 1R,4S,9S), isopyrazam (anti-epimeric enantiomer 1S,4R,9R), isopyrazam (syn epimeric racemate 1RS,4SR,9RS), isopyrazam (syn-epimeric enantiomer 1R,4S,9R), isopyrazam (syn-epimeric enantiomer 1S,4R,9S), mepronil, oxycarboxin, penflufen, penthiopyrad, sedaxane, thifluzamide, 1-methyl-N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide, 3-(difluoromethyl)-1-methyl-N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-1H-pyrazole-4-carboxamide, 3-(difluoromethyl)-N-[4-fluoro-2-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]-1-methyl-1H-pyrazole-4-carboxamide, N-[1-(2,4-dichlorophenyl)-1-methoxypropan-2-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, 5,8-difluoro-N-[2-(2-fluoro-4-{[4-(trifluoromethyl)pyridin-2-yl]oxy}phenyl)ethyl]quinazolin-4-amine, N-[9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, N-[(1S,4R)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide and N-[(1R,4S)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1Hpyrazole-4-carboxamide.

(3) inhibitors of the respiratory chain at complex III, for example ametoctradin, amisulbrom, azoxystrobin, cyazofamid, coumethoxystrobin, coumoxystrobin, dimoxystrobin, enestroburin, famoxadone, fenamidone, fenoxystrobin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyribencarb, triclopyricarb, trifloxystrobin, (2E)-2-(2-{[6-(3-chloro-2-methylphenoxy)-5-fluoropyrimidin-4-yl]oxy}phenyl)-2-(methoxyimino)-N-methylethanamide, (2E)-2-(methoxyimino)-N-methyl-2-(2-{[({(1E)-1-[3-(trifluoromethyl)phenyl]ethylidene}amino)oxy]methyl}phenyl)ethanamide, (2E)-2-(methoxyimino)-N-methyl-2-{2-[(E)-({1-[3-(trifluoromethyl)phenyl]ethoxy}imino)methyl]phenyl}-ethanamide, (2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-fluoro-2-phenylethenyl]oxy}phenyl)ethylidene]amino}-oxy)methyl]phenyl}-2-(methoxyimino)-N-methylethanamide, (2E)-2-{2-[({[(2E,3E)-4-(2,6-dichlorophenyl)but-3-en-2-ylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylethanamide, 2-chloro-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)pyridine-3-carboxamide, 5-methoxy-2-methyl-4-(2-[({(1E)-1-[3-(trifluoromethyl)phenyl]ethylidenelamino)oxy]methyl}phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one, methyl (2E)-2-{2-[({cyclopropyl[(4-methoxyphenyl)imino]methyl}-sulfanyl)methyl]phenyl}-3-methoxyprop-2-enoate, N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-(formyl-amino)-2-hydroxybenzamide, 2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide and 5 (2R)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide.

(4) Inhibitors of the mitosis and cell division, for example benomyl, carbendazim, chlorfenazole, diethofencarb, ethaboxam, fluopicolide, fuberidazole, pencycuron, thiabendazole, thiophanate-methyl, thiophanate, zoxamide, 5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl) [1,2,4]triazolo[1,5-a]pyrimidine and 3-chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-(2,4,6-trifluorophenyl)pyridazine.

(5) Compounds capable to have a multisite action, for example bordeaux mixture, captafol, captan, chlorothalonil, copper hydroxide, copper naphthenate, copper oxide, copper oxychloride, copper(2+) sulfate, dichlofluanid, dithianon, dodine, dodine free base, ferbam, fluorofolpet, folpet, guazatine, guazatine acetate, iminoctadine, iminoctadine albesilate, iminoctadine triacetate, mancopper, mancozeb, maneb, metiram, metiram zinc, oxine-copper, propamidine, propineb, sulphur and sulphur preparations including calcium polysulphide, thiram, tolylfluanid, zineb and ziram.

(6) Compounds capable to induce a host defence, for example acibenzolar-5-methyl, isotianil, probenazole and tiadinil.

(7) Inhibitors of the amino acid and/or protein biosynthesis, for example andoprim, blasticidin-S, cyprodinil, kasugamycin, kasugamycin hydrochloride hydrate, mepanipyrim, pyrimethanil and 3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinoline.

(8) Inhibitors of the ATP production, for example fentin acetate, fentin chloride, fentin hydroxide andsilthiofam.

(9) Inhibitors of the cell wall synthesis, for example benthiavalicarb, dimethomorph, flumorph, iprovalicarb, mandipropamid, polyoxins, polyoxorim, validamycin A and valifenalate.

(10) Inhibitors of the lipid and membrane synthesis, for example biphenyl, chloroneb, dicloran, edifenphos, etridiazole, iodocarb, iprobenfos, isoprothiolane, propamocarb, propamocarb hydrochloride, prothiocarb, pyrazophos, quintozene, tecnazene and tolclofos-methyl.

(11) Inhibitors of the melanine biosynthesis, for example carpropamid, diclocymet, fenoxanil, phthalide, pyroquilon, tricyclazole and 2,2,2-trifluoroethyl {3-methyl-1-[(4-methylbenzoyl)amino]butan-2-yl}carbamate.

(12) Inhibitors of the nucleic acid synthesis, for example benalaxyl, benalaxyl-M (kiralaxyl), bupirimate, clozylacon, dimethirimol, ethirimol, furalaxyl, hymexazol, metalaxyl, metalaxyl-M (mefenoxam), ofurace, oxadixyl and oxolinic acid.

(13) Inhibitors of the signal transduction, for example chlozolinate, fenpiclonil, fludioxonil, iprodione, procymidone, quinoxyfen 5 and vinclozolin.

(14) Compounds capable to act as an uncoupler, for example binapacryl, dinocap, ferimzone, fluazinam and meptyldinocap.

(15) Further compounds, for example benthiazole, bethoxazin, capsimycin, carvone, chinomethionat, pyriofenone (chlazafenone), cufraneb, cyflufenamid, cymoxanil, cyprosulfamide, dazomet, debacarb, dichlorophen, diclomezine, difenzoquat, difenzoquat methylsulphate, diphenylamine, ecomate, fenpyrazamine, flumetover, fluoroimide, flusulfamide, flutianil, fosetyl-aluminium, fosetyl-calcium, fosetyl-sodium, hexachlorobenzene, irumamycin, methasulfocarb, methyl isothiocyanate, metrafenone, mildiomycin, natamycin, nickel dimethyldithiocarbamate, nitrothal-isopropyl, octhilinone, oxamocarb, oxyfenthiin, pentachlorophenol and salts, phenothrin, phosphorous acid and its salts, propamocarb-fosetylate, propano sine-sodium, proquinazid, pyrimorph, (2E)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one, (2Z)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one, pyrroInitrine, tebufloquin, tecloftalam, tolnifanide, triazoxide, trichlamide, zarilamid, (3S,6S,7R,8R)-8-benzyl-3-[({3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2-yl}carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl 2-methylpropanoate, 1-(4-{4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone, 1-(4-{4-[(5S)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone, 1-(4-{4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone, 1-(4-methoxyphenoxy)-3,3-di-methylbutan-2-yl-1H-imidazole-1-carboxylate, 2,3,5,6-tetrachloro-4-(methylsulfonyl)pyridine, 2,3-dibutyl-6-chlorothieno[2,3-d]pyrimidin-4(3H)-one, 2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c]dipyrrole-1,3,5,7 (2H,6H)-tetrone, 2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[(5R)-5-phenyl-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone, 2-[5-methyl-3-(trifluoromethyl)-1Hpyrazol-1-yl]-1-(4-{4-[(5S)-5-phenyl-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone, 2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-{4-[4-(5-phenyl-4,5-dihydro-1,2-oxazol-3-yl)-1,3-thiazol-2-yl}piperidin-1-yl)ethanone, 2-butoxy-6-iodo-3-propyl-4H-chromen-4-one, 2-chloro-5-[2-chloro-1-(2,6-difluoro-4-methoxyphenyl)-4-methyl-1H-imidazol-5-yl]pyridine, 2-phenylphenol and salts, 3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline, 3,4,5-trichloropyridine-2,6-dicarbonitrile, 3-[5-(4-chlorophenyl)-2,3-dimethyl-1,2-oxazolidin-3-yl]pyridine, 3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridazine, 4-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3,6-dimethylpyridazine, 5-amino-1,3,4-thiadiazole-2-thiol, 5-chloro-N′-phenyl-N′-(prop-2-yn-1-yl)thiophene-2-sulfonohydrazide, 5-fluoro-2-[(4-fluorobenzyl)-oxy]pyrimidin-4-amine, 5-fluoro-2-[(4-methylbenzyl)oxy]pyrimidin-4-amine, 5-methyl-6-octyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine, ethyl (2Z)-3-amino-2-cyano-3-phenylprop-2-enoate, N′-(4-{[3-(4-chlorobenzyl)-1,2,4-thiadiazol-5-yl]oxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide, N-(4-chlorobenzyl)-3-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]propanamide, N-[(4-chlorophenyl)(cyano)methyl]-3-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]propanamide, N-[(5-bromo-3-chloropyridin-2-yl)-methyl]-2,4-dichloropyridine-3-carboxamide, N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2,4-dichloropyridine-3-carboxamide, N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2-fluoro-4-iodopyridine-3-carboxamide, N-{(E)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide, N-{(Z)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide, N′-{4-[(3-tert-butyl-4-cyano-1,2-thiazol-5-yl)oxy]-2-chloro-5-methylphenyl}-N-ethyl-N-methylimidoformamide, N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-(1,2,3,4-tetrahydronaphthalen-1-yl)-1,3-thiazole-4-carboxamide, N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}-piperidin-4-yl)-N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-1,3-thiazole-4-carboxamide, N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-[(1S)-1,2,3,4-tetrahydronaphthalen-1-yl]-1,3-thiazole-4-carboxamide, pentyl {6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)-methylidene]amino}oxy)methyl]pyridin-2-yl}carbamate, phenazine-1-carboxylic acid, quinolin-8-ol, quinolin-8-ol sulfate (2:1) and tert-butyl {6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)-methylene]amino}oxy)methyl]pyridin-2-yl}carbamate.

The active ingredients specified herein by their “common name” are known and described, for example, in the Pesticide Manual (“The Pesticide Manual”, 14th Ed., British Crop Protection Council 2006) or can be searched in the internet (e.g. http://www.alanwood.net/pesticides).

The composition according to the invention comprising a mixture with a bactericide compound may also be particularly advantageous. Examples of suitable bactericide mixing partners may be selected in the list consisting of bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furancarboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulphate and other copper preparations.

The various aspects of the invention will now be illustrated with reference to the following tables of compounds and examples. The following tables illustrate in a non limiting manner examples of compounds according to the invention.

Abbreviations which are used in the tables include the following:

Me=CH₃

Et=C₂H₅

n-Pr═CH₂CH₂CH₃

tert butyl ═C(CH₃)₃=t-Bu

cyclo-Pr=cyclopropyl

C₆H₅=phenyl

comm av.=commercially available

TABLE A

Compounds of formula (Ia)

(Ia)

embedded image

No.
X_n
R¹
R²
R³
R⁴
R⁵
R_m
cf.

Ia-1
3-Cl
COOMe
COOMe
H
H
H
2-CF₃
P16

5-CF₃

synthesis

procedure

Ia-2
3-Cl
H
H
CH₃
H
H
2-CF₃
P3

5-Cl

Ia-3
3-Cl
H
H
CH₃
H
H
2-CF₃
P3

5-Cl

NMR

Ia-4
3-Cl
COOEt
COOEt
H
H
H
2-CF₃
P16

5-CF₃

synthesis

procedure

Ia-5
3-Cl
COOMe
H
H
H
H
2-CF₃
P2

5-CF₃

NMR

Ia-6
3-Cl
COOMe
COOEt
H
H
H
2-CF₃
P2

5-CF₃

NMR

Ia-7
5-Br
OH
H
H
H
H
2-F
P3

6-F
NMR

Ia-8
3-Cl
H
H
CONHEt
H
H
4-OMe
Pl

5-CF₃

cpd. 301

Ia-9
3-Cl
H
H
CONHEt
H
H
2-Cl
P1

5-CF₃

6-Cl
cpd. 302

Ia-10
3-Cl
H
H
CONHEt
H
H
H
P1

5-CF₃

cpd. 304

Ia-11
3-Cl
H
H
CONHEt
H
H
4-Cl
P1

5-CF₃

cpd. 306

Ia-12
3-Cl
H
H
CONHEt
H
H
3-NO₂
P1

5-CF₃

cpd. 307

Ia-13
3-Cl
H
H
CONHEt
H
H
3-CF₃
P1

5-CF₃

cpd. 308

Ia-14
3-Cl
H
H
CONHEt
H
H
4-C₆H₅
P1

5-CF₃

Ia-15
3-Cl
H
H
CONHEt
H
H
2-Br
P1

5-CF₃

cpd. 310

Ia-16
3-Cl
H
H
CONHMe
H
H
2-Cl
P1

5-CF₃

6-Cl
cpd. 313

Ia-17
3-Cl
H
H
CONHMe
H
H
H
P1

5-CF₃

cpd. 314

Ia-18
3-Cl
H
H
CONHMe
H
H
4-OMe
P1

5-CF₃

cpd. 315

Ia-19
3-Cl
H
H
CONHMe
H
H
4-C₆H₅
P1

5-CF₃

cpd. 316

Ia-20
3-Cl
H
H
COOMe
H
H
H
P1

5-CF₃

cpd. 317

Ia-21
3-Cl
H
H
COOMe
H
H
2-Cl
P1

5-CF₃

6-Cl
cpd. 319

Ia-22
3-Cl
H
H
COOMe
H
H
4-C₆H₅
P1

5-CF₃

cpd. 320

Ia-23
3-Cl
H
H
COOMe
H
H
2-Br
P1

5-CF₃

cpd. 321

Ia-24
3-Cl
H
H
COOEt
H
H
4-OMe
P1

5-CF₃

cpd. 323

Ia-25
3-Cl
H
H
COOEt
H
H
3-CF₃
P1

5-CF₃

cpd. 324

Ia-26
3-Cl
H
H
COOEt
H
H
2-Cl
P1

5-CF₃

6-Cl
cpd. 325

Ia-27
3-Cl
H
H
COOEt
H
H
2-Br
P1

5-CF₃

cpd. 326

Ia-28
3-Cl
H
H
COOMe
H
H
4-OMe
P1

5-CF₃

cpd. 328

Ia-29
3-Cl
H
H
COOMe
H
H
4-Cl
P1

5-CF₃

cpd. 329

Ia-30
3-Cl
H
H
COOMe
H
H
3-NO₂
P1

5-CF₃

cpd. 330

Ia-31
3-Cl
H
H
COOMe
H
H
3-CF₃
P1

5-CF₃

cpd. 331

Ia-32
3-Cl
H
H
COOEt
H
H
H
P1

5-CF₃

cpd. 333

Ia-33
3-Cl
H
H
COOEt
H
H
4-Cl
P1

5-CF₃

cpd. 334

Ia-34
3-Cl
H
H
COOEt
H
H
3-NO₂
P1

5-CF₃

cpd. 335

Ia-35
3-Cl
H
H
COOEt
H
H
4-C₆H₅
P1

5-CF₃

cpd. 336

Ia-36
3-Cl
H
H
CONHMe
H
H
4-Cl
P1

5-CF₃

cpd. 337

Ia-37
3-Cl
H
H
CONHMe
H
H
3-NO₂
P1

5-CF₃

cpd. 338

Ia-38
3-Cl
H
H
CONHMe
H
H
3-CF₃
P1

5-CF₃

cpd. 339

Ia-39
3-Cl
H
H
CONHMe
H
H
2-Br
P1

5-CF₃

cpd. 340

Ia-40
3-Cl
H
H
COOH
H
H
2-Cl
P2

5-CF₃

6-Cl

Ia-41
3-Cl
CH₃
H
H
H
H
4-CF₃
NMR

5-CF₃

Ia-42
3-Cl
CH₃
H
H
H
H
3-CF₃

5-CF₃

Ia-43
3-Cl
H
H
Me
H
H
2-CF₃
P2

5-CF₃

cpd. 38

Ia-44
5-CF₃
CH₂—CH₂
H
H
H
2-CF₃
P2

cpd. 65

Ia-45
3-Cl
CH₂—CH₂
H
H
H
2-CF₃
P3

5-Cl

cpd. 67

Ia-46
5-CF₃
CH₃
H
H
H
H
2-CF₃
P2

cpd. 66

Ia-47
5-CF₃
CH₃
H
H
H
H
2-I
P2

cpd. 67

Ia-48
5-Cl
CH₂—CH₂
H
H
H
2-CF₃
P3

cpd. 68

Ia-49
5-CF₃
CH₃
H
H
H
H
2-CF₃
P2

6-Cl

cpd. 62

Ia-50
5-CF₃
CH₃
H
H
H
H
2-I
P2

6-Cl

cpd. 63

Ia-51
5-CF₃
CH₃
H
H
H
H
2-Br
P2

6-Cl

cpd. 64

Ia-52
3-Cl
NHCO-2-C₆H₄Cl
H
H
H
H
2-CF₃
P2

5-CF₃

cpd. 70

Ia-53
3-Cl
NHCO-2-C₆H₄Cl
H
H
H
H
2-I
P2

5-CF₃

cpd. 71

Ia-54
3-Cl
NHCO-2-C₆H₄Cl
H
H
H
H
2-Br
P2

5-CF₃

cpd. 72

Ia-55
3-F
COO-tert butyl
COO-tert
H
H
H
2-CF₃
P3

5-Cl

butyl

NMR

6-F

Ia-56
5-Cl
CH₃
H
H
H
H
2-Cl
P3

4-F
NMR

Ia-57
5-Cl
CH₃
H
H
H
H
2-Cl
P3

5-F
cpd. 7

Ia-58
3-Cl
CH₃
H
H
H
H
2-Cl
P2

5-CF₃

3-Cl
cpd. 1

Ia-59
3-Cl
CH₃
H
H
H
H
2-Cl
P2

5-CF₃

4-Cl
cpd. 2

Ia-60
3-Cl
CH₃
H
H
H
H
2-Cl
P2

5-CF₃

5-Cl
cpd. 3

Ia-61
3-Cl
CH₃
H
H
H
H
2-OMe
P2

5-CF₃

cpd. 4

Ia-62
3-Cl
CH₃
H
H
H
H
2-OMe
P2

5-CF₃

3-OMe
cpd. 5

Ia-63
3-Cl
CH₃
H
H
H
H
2-OMe
P2

5-CF₃

6-OMe
cpd. 6

Ia-64
3-Cl
CH₃
H
H
H
H
2-Me
P2

5-CF₃

cpd. 7

Ia-65
3-Cl
CH₃
H
H
H
H
2-Me
P2

5-CF₃

3-Me
cpd. 8

Ia-66
3-Cl
CH₃
H
H
H
H
2-Me
P2

5-CF₃

4-Me
cpd. 9

Ia-67
3-Cl
CH₃
H
H
H
H
2-Me
P2

5-CF₃

5-Me
cpd. 10

Ia-68
3-Cl
CH₃
H
H
H
H
2-F
P2

5-CF₃

3-Cl
cpd. 11

Ia-69
3-Cl
CH₃
H
H
H
H
2-Me
P2

5-CF₃

3-Cl
cpd. 12

Ia-70
3-Cl
CH₃
H
H
H
H
2-Me
P2

5-CF₃

3-F
cpd. 13

Ia-71
3-Cl
CH₃
H
H
H
H
2-F
P2

5-CF₃

5-Cl
cpd. 14

Ia-72
3-Cl
CH₃
H
H
H
H
2-Me
P2

5-CF₃

3-OH
cpd. 15

Ia-73
3-Cl
C₂H₅
H
H
H
H
2-Cl
P2

5-CF₃

3-Cl
cpd. 16

Ia-74
3-Cl
C₂H₅
H
H
H
H
2-Cl
P2

5-CF₃

4-Cl
NMR

Ia-75
3-Cl
C₂H₅
H
H
H
H
2-Cl
P2

5-CF₃

5-Cl
cpd. 18

Ia-76
3-Cl
C₂H₅
H
H
H
H
2-NHMe
P2

5-CF₃

cpd. 19

Ia-77
3-Cl
C₂H₅
H
H
H
H
2-OMe
P2

5-CF₃

cpd. 20

Ia-78
3-Cl
C₂H₅
H
H
H
H
2-OMe
P2

5-CF₃

3-OMe
cpd. 21

Ia-79
2-Cl
C₂H₅
H
H
H
H
2-OMe
P2

5-CF₃

6-OMe
cpd. 22

Ia-80
3-Cl
C₂H₅
H
H
H
H
2-OH

5-CF₃

Ia-81
3-Cl
C₂H₅
H
H
H
H
2-OH
NMR

5-CF₃

4-OMe

Ia-82
3-Cl
C₂H₅
H
H
H
H
2-OH

5-CF₃

5-Me

Ia-83
3-Cl
C₂H₅
H
H
H
H
2-Me
P2

5-CF₃

cpd. 23

Ia-84
3-Cl
C₂H₅
H
H
H
H
2-Me
P2

5-CF₃

3-Me
cpd. 24

Ia-85
3-Cl
C₂H₅
H
H
H
H
2-Me
P2

5-CF₃

4-Me
cpd. 25

Ia-86
3-Cl
C₂H₅
H
H
H
H
2-F
P2

F—CF₃

3-Cl
cpd. 26

Ia-87
3-Cl
C₂H₅
H
H
H
H
2-Me
P2

5-CF₃

3-Cl
cpd. 27

Ia-88
3-Cl
C₂H₅
H
H
H
H
2-Me
P2

5-CF₃

3-F
cpd. 28

Ia-89
3-Cl
C₂H₅
H
H
H
H
2-F
P2

5-CF₃

5-Cl
cpd. 29

Ia-90
3-Cl
C₂H₅
H
H
H
H
2-Me
P2

5-CF₃

3-OH
cpd. 30

Ia-91
3-Cl
C₂H₅
H
H
H
H
2-Me
P2

5-CF₃

5-Me
cpd. 31

Ia-92
3-Cl
CH₃
H
H
H
H
2-CF₃
P2

5-CF₃

cpd. 32

Ia-93
3-Cl
CH₃
CH₃
H
H
H
2-CF₃
P2

5-CF₃

cpd. 33

Ia-94
3-Cl
CH₃
C₂H₅
H
H
H
2-CF₃
P2

5-CF₃

cpd. 34

Ia-95
3-Cl
n-Pr
n-Pr
H
H
H
2-CF₃
P2

5-CF₃

cpd. 35

Ia-96
3-Cl
n-Pr
n-Pr
H
H
H
2-I
P2

5-CF₃

cpd. 36

Ia-97
3-Cl
n-Pr
n-Pr
H
H
H
2-Br
P2

5-CF₃

cpd. 37

Ia-98¹
3-Cl
H
(CH₂)₄
H
H
2-CF₃
P4

5-CF₃

cpd. 1

Ia-99²
3-Cl
H
(CH₂)₄
H
H
2-CF₃
P4

5-CF₃

cpd. 2

Ia-100
3-Cl
C₂H₅
H
H
H
H
2-CF₃
P2

5-CF₃

cpd. 39

Ia-101
3-Cl
C₂H₅
H
H
H
H
2-Br
P2

5-CF₃

cpd. 40

Ia-102
3-Cl
C₂H₅
H
H
H
H
2-CHF₂
P2

5-CF₃

cpd. 41

Ia-103
3-Cl
n-Pr
H
H
H
H
2-CF₃
P2

5-CF₃

cpd. 42

Ia-104
3-Cl
n-Pr
H
H
H
H
2-Br
P2

5-CF₃

cpd. 43

Ia-105
3-Cl
n-Pr
H
H
H
H
2-CHF₂
P2

5-CF₃

cpd. 44

Ia-106
3-Cl
CH₃
CH₃
H
H
H
2-CHF₂
P2

5-CF₃

cpd. 46

Ia-107
3-Cl
H
(CH₂)₄
H
H
2-CHF₂
P4

5-CF₃

cpd. 3

Ia-108¹
3-Cl
H
(CH₂)₄
H
H
2-I
P4

5-CF₃

cpd. 4

Ia-109²
3-Cl
H
(CH₂)₄
H
H
2-I
P4

5-CF₃

cpd. 5

Ia-110
3-Cl
H
H
C₂H₅
H
H
2-CF₃
P2

5-CF₃

cpd. 47

Ia-111
3-Cl
H
H
OMe
H
H
2-CF₃
P2

5-CF₃

NMR

Ia-112
3-Cl
H
H
OC(O)Me
H
H
2-CF₃
P2

5-CF₃

NMR

Ia-113
3-Cl
CH₃
H
H
H
H
2-CF₃
P3

5-Cl

cpd. 60

Ia-114
3-Cl
CH₃
H
H
H
H
2-I
P3

5-Cl

cpd. 61

Ia-115
3-Cl
H
H
C₆H₅
H
H
2-CF₃
P2

5-CF₃

cpd. 49

Ia-116
3-Cl
H
H
C₆H₅
H
H
2-I
P2

5-CF₃

cpd. 50

Ia-117
3-Cl
NHCO-2,6-C₆H₃Cl₂
H
H
H
H
2-I
P2

5-CF₃

cpd. 51

Ia-118
3-Cl
NHCO-2,6-C₆H₃Cl₂
H
H
H
H
2-Br
P2

5-CF₃

cpd. 52

Ia-119
3-Cl
NHCO-2,6-C₆H₃Cl₂
H
H
H
H
2-CHF₂
P2

5-CF₃

cpd. 53

Ia-120
3-Cl
CN
COOMe
H
H
H
2-CF₃
P2

5-CF₃

cpd. 54

Ia-121
3-Cl
CN
H
H
H
H
2-CF₃
P2

5-CF₃

cpd. 55

Ia-122³
3-Cl
H
H
CH₃
H
H
2-CF₃
P2

5-CF₃

cpd. 57

Ia-123³
3-Cl
H
H
CH₃
H
H
2-CF₃
P2

5-CF₃

cpd. 56

Ia-124
5-Cl
CH₃
H
H
H
H
2-I
P3

cpd. 65

Ia-125
5-Cl
CH₃
H
H
H
H
2-CF₃
P3

cpd. 66

Ia-126
3-Cl
CH₃
H
CH₃
H
H
2-CF₃
P2

5-CF₃

cpd. 58

Ia-127
3-Cl
CH₃
H
CH₃
H
H
2-I
P2

5-CF₃

cpd. 59

Ia-128
3-Cl
H
(CH₂)₅
H
H
2-CF₃
P4

5-CF₃

cpd. 6

Ia-129
3-Cl
H
(CH₂)₅
H
H
2-I
P4

5-CF₃

cpd. 7

Ia-130
5-Cl
C₆H₅
H
H
H
H
2-CF₃
P3

NMR

Ia-131
5-Cl
C₂H₅
H
H
H
H
2-CF₃
P3

NMR

Ia-132
6-Cl
H
H
CH₃
H
H
2-CF₃
P2

5-CF₃

cpd. 61

Ia-133
3-Cl
H
H
CF₃
H
H
2-CF₃
P2

5-CF₃

cpd. 60

Ia-134
5-Cl
(CH₂)₄
H
H
H
2-CF₃
P3

NMR

Ia-135
3-Cl
H
H
CH₃
H
cyclo-Pr
2-CF₃
P2

5-CF₃

cpd. 68

Ia-136
3-Cl
H
H
CH₃
H
cyclo-Pr
2-I
P2

5-CF₃

cpd. 69

Ia-137
3-Cl
H
(CH₂)₄
H
H
2-CF₃
P5

5-Cl

cpd. 1

Ia-138
3-Cl
C₂H₅
H
H
H
H
H

5-CF₃

Ia-139
3-Cl
F
F
H
H
H
2-CF₃
P3

5-Cl

NMR

Ia-140
3-Cl
H
H
CH₃
H
H
2-I
P2

5-CF₃

NMR

Ia-141
3-Cl
H
H
CH₃
H
H
2-Cl
P2

5-CF₃

NMR

Ia-142
3-Cl
F
F
H
H
H
2-I
P3

5-Cl

NMR

Ia-143⁴
3-Cl
CH₂-cyclo-Pr
H
CH₃
H
H
2-CF₃
NMR

5-CF₃

Ia-144⁴
3-Cl
CH₂—CH═CH₂
H
CH₃
H
H
2-CF₃
P2

5-CF₃

NMR

Ia-145⁴
3-Cl
CH₂—CH═CH₂
H
CH₃
H
H
2-Cl
P2

5-CF₃

Ia-146⁴
3-Cl
CH₂-cyclo-Pr
H
CH₃
H
H
2-Cl
NMR

5-CF₃

Ia-147²
3-Cl
H
CH₂
H
H
2-CF₃
P5

5-Cl

cpd. 2

Ia-148
3-Cl
F
F
H
H
H
2-CF₃
P2

5-CF₃

NMR

Ia-149
3-Cl
H
CH₂
H
H
2-I
P5

5-Cl

NMR

Ia-150
3-Cl
F
F
H
H
H
2-I
P2

5-CF₃

NMR

Ia-151
3-Cl
H
CH₂
H
H
2-I
P5

5-Cl

cpd. 4

Ia-152²
3-Cl
H
CH₂
H
H
2-I
P5

5-Cl

cpd. 3

Ia-153
3-Cl
H
H
CH₃
H
H
2-Br
P2

5-CF₃

NMR

Ia-154
3-Cl
H
H
CH₃
H
H
2-CHF₂
P2

5-CF₃

NMR

Ia-155⁴
3-Cl
CH₂—C≡CH
H
CH₃
H
H
2-Br
P2

5-CF₃

NMR

Ia-156⁴
3-Cl
CH₂—C≡CH
H
CH₃
H
H
2-CHF₂
P2

5-CF₃

NMR

Ia-157
3-Cl 5-CF₃
C₂H₅
H
H
H
H

embedded image

NMR

Ia-158
3-Cl
OC(O)Me
H
H
H
H
2-CF₃
P2

5-CF₃

Ia-159
3-Cl
OC(O)Me
H
H
H
COMe
2-CF₃
P2

5-CF₃

Ia-160
3-Cl
Cl
H
H
H
H
2-CF₃
P2

5-CF₃

Ia-161⁴
3-Cl
H
(CH₂)₄
H
H
H
P4

5-CF₃

NMR

Ia-162⁴
3-Cl
H
(CH₂)₄
H
H
4-Cl
P4

5-CF₃

NMR

Ia-163⁴
3-Cl
H
(CH₂)₄
H
H
4-OMe
PR

5-CF₃

NMR

Ia-164⁴
3-Cl
H
(CH₂)₄
H
H
2-Br
P4

5-CF₃

NMR

Ia-165⁴
3-Cl
H
(CH₂)₄
H
H
4-C₆H₅
NMR

5-CF₃

Ia-166⁴
3-Cl
H
(CH₂)₄
H
H
3-NO₂
P4

5-CF₃

NMR

Ia-167
3-Cl
COOEt
H
H
H
H
2-CF₃
P2

5-CF₃

Ia-168
3-Cl
OEt
H
H
H
H
2-CF₃
P2

5-CF₃

Ia-169
3-Cl
H
H
COOH
H
H
2-Br
P2

5-CF₃

NMR

Ia-170
3-Cl
H
H
CH₃
H
H
2-F
P2

5-CF₃

6-F
NMR

Ia-171
3-Cl
H
H
CH₃
H
H
2-F
P2

5-CF₃

4-F
NMR

6-F

Ia-172
3-Cl
H
H
CH₃
H
H
2-F
P2

5-CF₃

NMR

Ia-173
3-Cl
H
H
CH₃
H
H
2-Cl
P2

5-CF₃

6-Cl
NMR

Ia-174
3-Cl
H
H
CH₃
H
H
2-F
P2

5-CF₃

6-CF₃
NMR

Ia-175
3-Cl
H
H
CH₃
H
H
2-CH₂CF₃
P2

5-CF₃

NMR

Ia-176
3-Cl
H
H
CH₃
H
H
2-Cl
P2

5-CF₃

4-Cl
NMR

Ia-177
3-Cl
CH₃
H
H
H
H
2-I
P2

5-CF₃

NMR

Ia-178
3-Cl
CH₃
H
C₂H₅
H
H
2-I
P2

5-CF₃

NMR

Ia-179
3-Cl
CH₃
H
C₂H₅
H
H
2-CF₃
P2

5-CF₃

Ia-180
3-Cl
CH₃
H
C₂H₅
H
H
2-I
P3

5-Cl

Ia-181
3-Cl
CH₃
H
C₂H₅
H
H
2-CF₃
P3

5-Cl

Ia-182
3-Cl
C₂H₅
H
CH₃
H
H
2-I
P3

5-Cl

Ia-183
3-Cl
C₂H₅
H
CH₃
H
H
2-CF₃
P3

5-Cl

Ia-184
5-F
CH₃
H
CH₃
H
H
2-I
P3

Ia-185
5-F
CH₃
H
CH₃
H
H
2-CF₃
P3

Ia-186
3-Cl
CH₃
H
CH₃
H
H
2-I
P3

Ia-187
3-Cl
CH₃
H
CH₃
H
H
2-CF₃
P3

Ia-188
5-CF₃
CH₃
H
CH₃
H
H
2-I
P2

Ia-189
5-CF₃
CH₃
H
CH₃
H
H
2-CF₃
P2

Ia-190
3-Cl
H
H
CH₂—OCH₃
H
H
2-I
P3

5-Cl

Ia-191
3-Cl
H
H
CH₂—OCH₃
H
H
2-CF₃
P3

5-Cl

Ia-192
3-Cl
H
H
C₂H₅
H
H
2-I
P3

5-Cl

Ia-193
3-Cl
H
H
C₂H₅
H
H
2-CF₃
P3

5-Cl

Ia-194
3-Cl
H
H
CH₂—OH
H
H
2-I
P2

5-CF₃

Ia-195
3-Cl
H
H
CH₂—OH
H
H
2-CF₃
P2

5-CF₃

Ia-196
3-Cl
H
H
CH₃
H
H
2-NO₂
P2

5-CF₃

NMR

Ia-197
3-Cl
N(CH₃)₂
H
H
H
H
3-Cl
P2

5-CF₃

NMR

Ia-198
3-Cl
N(CH₃)₂
H
H
H
H
2-F
P2

5-CF₃

6-F
NMR

Ia-199
3-Cl
N(CH₃)₂
H
H
H
H
H
P2

5-CF₃

NMR

Ia-200
3-Cl
N(CH₃)₂
H
H
H
H
4-Cl
P2

5-CF₃

NMR

Ia-201
3-Cl
N(CH₃)₂
H
H
H
H
2-Cl
P2

5-CF₃

4-Cl
NMR

Ia-202
3-Cl
N(CH₃)₂
H
H
H
H
2-Cl
P2

5-CF₃

6-Cl
NMR

Ia-203
3-Cl 5-CF₃

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H
H
H
H
H
P2 NMR

Ia-204
3-Cl 5-CF₃

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H
H
H
H
2-Cl 4-Cl
P2 NMR

Ia-205
3-Cl 5-CF₃

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H
H
H
H
2-CF₃
P2 NMR

Ia-206
3-Cl 5-CF₃

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H
H
H
H
4-Cl
P2 NMR

Ia-207
3-Cl 5-CF₃

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H
H
H
H
2-F 6-F
P2 NMR

Ia-208
3-Cl 5-CF₃

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H
H
H
H
2-Cl 6-Cl
P2 NMR

Ia-209
3-Cl 5-CF₃

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H
H
H
H
2-Cl
P2 NMR

Ia-210
3-Cl 5-CF₃

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H
H
H
H
3-Cl
P2 NMR

Ia-211
3-Cl
N(CH₃)₂
H
H
H
H
2-Cl
P2

5-CF₃

NMR

Ia-212
3-Cl
N(CH₃)₂
H
H
H
H
2-CF₃
P2

5-CF₃

NMR

Ia-213
3-Cl
4-Cl—Phenyl
H
H
H
H
2-CF₃
P3

5-Cl

NMR

Ia-214
3-Cl
CH₃
H
H
H
H
2-NO₂
P3

5-Cl

NMR

Ia-215
3-Cl
CH₃
H
C₂H₅
H
H
2-NO₂
P2

5-CF₃

NMR

Ia-216
3-Cl
CH₃
H
C₂H₅
H
H
2-F
P2

5-CF₃

6-F
NMR

Ia-217
3-Cl
CH₃
COOEt
H
H
H
2-NO₂

5-Cl

Ia-218
3-Cl
CH₃
COOEt
H
H
H
2-CF₃

5-Cl

¹cis-isomer,

²trans-isomer,

³pure enantiomer, absolute configuration not determined,

⁴mixture of diastereomers

¹H-NMR Data

¹H-NMR-data were determined with a Bruker Avance 400 equipped with a flow cell (60 μl volume) or with a Bruker AVIII 400 equipped with 1.7 mm cryo-CPTCI probe head or with a Bruker AVII 600 (600.13 MHz) equipped with a cyroTCI probe head or with a Bruker AVIII 600 (601.6 MHz) equipped with a cryo CPMNP probe head with tetramethylsilane as reference (0.0) and the solvents CD₃CN, CDCl₃, [D₆]-DMSO.

NMR-data of selected examples are listed in classic format (chemical shift 8, multiplicity, number of hydrogen atoms) or as NMR-peak-lists.

NMR-Peak-Lists:

If NMR-data of selected examples are provided in form of ¹H-NMR-peak lists, then for every peak first the chemical shift 8 in ppm and then, separated by a blank, the intensity of the signal in round brackets is listed.

The peak list of an example is therefore listed as: δ₁(intensity₁); δ₂(intensity₂) . . . δ_i(intensity_i); . . . ; δ_n(intensity_n).

The solvent, in which the NMR-spectrum was measured, is specified in squared brackets.

No. Ia-3, Solvent: <CDCl₃>, Spectrometer: 400.13 MHz

8.3588 (6.16); 8.3534 (6.06); 7.7243 (6.40); 7.7189 (6.17); 7.6848 (2.78); 7.6655 (3.42); 7.5937 (1.05); 7.5755 (2.97); 7.5578 (2.63); 7.5355 (2.44); 7.5166 (2.76); 7.4977 (0.98); 7.4512 (3.33); 7.4333 (2.42); 7.2634 (2.41); 6.6512 (1.15); 6.6315 (1.14); 5.0999 (0.41); 4.7466 (0.67); 4.7297 (1.27); 4.7163 (1.28); 4.7129 (1.54); 4.7097 (1.17); 4.6961 (1.28); 4.6792 (0.66); 3.2377 (1.21); 3.2202 (1.07); 3.2013 (4.18); 3.1838 (4.36); 3.1756 (4.15); 3.1627 (4.10); 3.1392 (1.14); 3.1263 (1.01); 2.3460 (0.70); 1.6114 (12.84); 1.3745 (0.37); 1.3578 (0.39); 1.3402 (0.63); 1.3242 (16.00); 1.3075 (15.48); 1.2746 (0.33); 1.2579 (0.50); 0.0003 (3.34)

No. Ia-5, Solvent: <[D₆]-DMSO>, Spectrometer: 400.13 MHz

8.9835 (1.54); 8.9815 (1.84); 8.9787 (1.83); 8.9770 (1.62); 8.6360 (0.51); 8.6218 (1.05); 8.6071 (0.51); 8.5524 (1.78); 8.5512 (1.90); 8.5475 (1.89); 7.7486 (1.10); 7.7291 (1.53); 7.7187 (0.54); 7.7000 (1.28); 7.6813 (0.92); 7.6405 (0.91); 7.6217 (1.13); 7.6026 (0.42); 7.3990 (1.32); 7.3803 (1.18); 4.7833 (0.83); 4.7684 (1.05); 4.7628 (1.12); 4.7478 (0.91); 4.0732 (0.39); 4.0582 (0.77); 4.0429 (0.56); 4.0400 (0.66); 4.0249 (1.00); 4.0100 (0.49); 3.8681 (0.51); 3.8536 (0.59); 3.8473 (0.54); 3.8335 (0.79); 3.8205 (0.45); 3.8140 (0.45); 3.7996 (0.38); 3.6409 (16.00); 3.3266 (32.02); 3.3028 (1.01); 2.5161 (4.83); 2.5116 (10.58); 2.5070 (14.78); 2.5024 (10.69); 2.4978 (4.94); 0.0054 (7.40)

No. Ia-6, Solvent: <CD₃CN>, Spectrometer: 600.13 MHz

8.7760 (2.18); 8.1985 (1.98); 8.1964 (2.12); 7.6884 (1.37); 7.6756 (1.67); 7.6082 (0.57); 7.5958 (1.48); 7.5841 (1.09); 7.5704 (1.14); 7.5578 (1.37); 7.5453 (0.49); 7.1727 (1.48); 7.1603 (1.37); 7.0970 (0.46); 7.0878 (0.75); 7.0782 (0.48); 4.4917 (2.35); 4.4862 (2.57); 4.4808 (2.44); 4.4753 (2.50); 4.2907 (0.69); 4.2845 (0.54); 4.2789 (0.71); 4.2727 (1.47); 4.2609 (1.45); 4.2555 (0.54); 4.2490 (0.52); 4.2436 (1.49); 4.2317 (1.50); 4.2256 (0.72); 4.2199 (0.52); 4.2137 (0.69); 3.7701 (16.00); 2.1546 (2.03); 1.9495 (1.18); 1.9454 (2.18); 1.9413 (3.16); 1.9373 (2.23); 1.9332 (1.15); 1.2383 (0.62); 1.2333 (4.10); 1.2265 (1.26); 1.2215 (8.17); 1.2147 (0.72); 1.2096 (4.00); −0.0001 (1.33)

No. Ia-7, Solvent: <CD₃CN>, Spectrometer: 400.13 MHz

3.65 (m, 1H); 3.8 (m, 1H); 4.2 (br., 1H); 4.85 (m, 1H); 7.1 (m, 3H); 7.5 (m, 2H); 7.95 (d, 1H); 9.65 (s, 1H)

No. Ia-41, Solvent: <[D₆]-DMSO>, Spectrometer: 601.6 MHz 8.9659 (4.86); 8.9642 (4.79); 8.7601 (1.29); 8.7505 (2.33); 8.7409 (1.27); 8.3952 (5.03); 8.3925 (4.80); 8.1322 (0.89); 8.1190 (0.97); 8.0721 (0.51); 7.9561 (5.51); 7.9426 (6.83); 7.8960 (0.41); 7.8818 (0.60); 7.8684 (0.64); 7.8546 (0.61); 7.8347 (7.13); 7.8210 (5.73); 7.8128 (0.46); 3.9028 (7.65); 3.8937 (1.28); 3.8823 (2.48); 3.8709 (2.50); 3.8594 (1.34); 3.7085 (1.13); 3.7036 (0.40); 3.6979 (2.13); 3.6928 (0.48); 3.6870 (2.49); 3.6762 (2.51); 3.6655 (1.22); 3.6223 (0.34); 3.5141 (1.42); 3.5051 (1.76); 3.5019 (1.48); 3.4926 (2.55); 3.4834 (1.28); 3.4801 (1.30); 3.4712 (1.09); 3.3176 (207.29); 3.1726 (1.00); 3.1639 (0.98); 2.6191 (1.05); 2.6160 (2.21); 2.6130 (3.06); 2.6099 (2.20); 2.6069 (1.04); 2.5405 (0.77); 2.5369 (0.54); 2.5335 (0.53); 2.5223 (6.53); 2.5192 (8.17); 2.5161 (8.37); 2.5073 (168.28); 2.5043 (360.66); 2.5012 (494.89); 2.4982 (361.70); 2.4952 (167.19); 2.4764 (0.47); 2.4735 (0.50); 2.4705 (0.43); 2.3914 (0.99); 2.3885 (2.14); 2.3854 (2.98); 2.3824 (2.08); 2.3794 (0.91); 1.9084 (1.16); 1.8473 (0.77); 1.5141 (2.61); 1.2701 (15.85); 1.2587 (16.00); 1.2495 (0.54); 1.2354 (0.88); 1.1515 (0.35); 1.1471 (0.35); 1.1405 (0.34); 0.0965 (1.43); 0.0154 (0.41); 0.0052 (11.38); −0.0002 (375.37); −0.0058 (11.58); −0.1001 (1.41)

No. Ia-55, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

7.6988 (0.40); 7.6728 (0.32); 7.2565 (0.33); 4.1621 (0.60); 4.1462 (0.60); 3.9041 (1.02); 3.3405 (58.94); 2.5249 (0.54); 2.5115 (8.95); 2.5072 (17.93); 2.5026 (23.78); 2.4981 (17.89); 2.4937 (9.15); 1.4320 (16.00); −0.0002 (0.43)

No. Ia-56, Solvent: <[D₆]-DMSO>, Spectrometer: 601.6 MHz

8.5658 (4.95); 8.5654 (4.95); 8.5617 (4.99); 8.4576 (1.18); 8.4481 (2.33); 8.4386 (1.21); 7.8566 (4.17); 7.8523 (4.09); 7.8427 (4.48); 7.8384 (4.48); 7.4698 (3.43); 7.4656 (3.45); 7.4548 (3.52); 7.4506 (3.39); 7.3845 (3.04); 7.3742 (3.28); 7.3703 (3.89); 7.3598 (8.90); 7.3456 (5.16); 7.2631 (2.19); 7.2589 (2.02); 7.2490 (3.96); 7.2448 (3.53); 7.2348 (1.86); 7.2306 (1.67); 3.9026 (6.02); 3.5174 (0.87); 3.5074 (1.18); 3.5048 (1.09); 3.4954 (2.30); 3.4857 (1.80); 3.4830 (2.06); 3.4731 (1.76); 3.4528 (1.54); 3.4428 (2.23); 3.4419 (2.22); 3.4317 (2.45); 3.4199 (1.21); 3.4102 (0.94); 3.3171 (138.62); 3.2192 (1.29); 3.2075 (2.45); 3.1957 (2.36); 3.1839 (1.18); 3.1722 (1.35); 3.1635 (1.12); 2.6186 (0.59); 2.6157 (1.28); 2.6126 (1.81); 2.6096 (1.30); 2.6066 (0.60); 2.5402 (0.35); 2.5219 (3.33); 2.5188 (4.20); 2.5157 (4.13); 2.5069 (96.83); 2.5039 (210.66); 2.5008 (291.97); 2.4978 (214.78); 2.4948 (100.92); 2.4790 (0.83); 2.4757 (0.63); 2.3911 (0.58); 2.3881 (1.28); 2.3850 (1.78); 2.3820 (1.27); 2.3790 (0.58); 1.2550 (16.00); 1.2434 (15.96); 0.0965 (0.80); 0.0052 (6.40); −0.0002 (215.80); −0.0058 (6.79); −0.1001 (0.81)

No. Ia-74, Solvent: <[D₆]-DMSO>, Spectrometer: 601.6 MHz

8.9682 (4.75); 8.9663 (4.63); 8.4727 (1.40); 8.4628 (2.53); 8.4538 (1.23); 8.4155 (5.01); 8.4126 (4.95); 7.6249 (7.08); 7.6215 (7.26); 7.4590 (3.83); 7.4556 (3.69); 7.4453 (4.62); 7.4419 (4.53); 7.3280 (8.14); 7.3143 (6.76); 3.9026 (7.66); 3.7407 (0.42); 3.7316 (1.01); 3.7269 (0.98); 3.7223 (0.93); 3.7179 (1.98); 3.7061 (2.35); 3.7017 (1.31); 3.6966 (2.24); 3.6863 (1.91); 3.6761 (2.04); 3.6666 (1.04); 3.5023 (0.88); 3.4936 (1.41); 3.4897 (1.30); 3.4811 (1.94); 3.4728 (1.19); 3.4594 (0.84); 3.3170 (195.39); 3.1723 (0.90); 3.1635 (0.88); 2.6186 (0.85); 2.6156 (1.76); 2.6126 (2.41); 2.6097 (1.74); 2.6067 (0.83); 2.5403 (0.54); 2.5219 (5.10); 2.5189 (6.50); 2.5157 (7.21); 2.5069 (137.75); 2.5039 (284.67); 2.5009 (387.37); 2.4979 (283.44); 2.4949 (133.11); 2.4736 (0.46); 2.4707 (0.36); 2.3910 (0.81); 2.3881 (1.70); 2.3851 (2.34); 2.3821 (1.66); 2.3792 (0.76); 1.8030 (0.34); 1.7935 (0.75); 1.7808 (2.09); 1.7716 (1.80); 1.7683 (2.94); 1.7592 (1.88); 1.7557 (2.41); 1.7424 (1.48); 1.7324 (0.71); 1.7198 (0.45); 1.2492 (0.39); 1.2371 (0.41); 0.8756 (0.42); 0.8625 (0.46); 0.8429 (0.33); 0.7843 (7.42); 0.7720 (16.00); 0.7596 (7.12); 0.0965 (1.05); 0.0052 (9.03); −0.0002 (243.85); −0.0057 (7.74); −0.1001 (1.06)

No. Ia-81, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

12.8703 (4.77); 8.9950 (1.95); 8.9924 (1.93); 8.6551 (0.54); 8.6403 (1.00); 8.4049 (1.99); 8.4011 (1.99); 7.6614 (2.23); 7.6391 (2.31); 6.4387 (1.26); 6.4324 (1.56); 6.4166 (1.13); 6.4103 (1.65); 6.3856 (3.14); 6.3793 (2.36); 3.9046 (4.60); 3.7499 (16.00); 3.7327 (1.24); 3.7186 (1.12); 3.7037 (0.97); 3.6889 (0.43); 3.5358 (0.63); 3.5232 (0.34); 3.5099 (0.42); 3.4888 (0.61); 3.4654 (1.14); 3.4518 (1.49); 3.3753 (509.95); 3.3070 (0.98); 3.2883 (0.52); 3.1753 (0.37); 3.1623 (0.35); 2.6787 (0.41); 2.6744 (0.58); 2.6699 (0.45); 2.5445 (0.44); 2.5276 (1.80); 2.5142 (33.64); 2.5098 (67.47); 2.5053 (89.50); 2.5007 (67.49); 2.4964 (34.39); 2.3364 (0.41); 2.3321 (0.57); 2.3275 (0.43); 1.8053 (0.65); 1.7868 (1.09); 1.7753 (0.81); 1.7697 (0.91); 1.7569 (0.74); 0.7697 (2.72); 0.7512 (6.02); 0.7327 (2.60); 0.0080 (0.48); −0.0002 (14.94); −0.0085 (0.58)

No. Ia-111, Solvent: <[D₆]-DMSO>, Spectrometer: 601.6 MHz

9.0203 (11.61); 9.0185 (11.20); 8.9667 (2.43); 8.9650 (2.35); 8.6215 (3.27); 8.6118 (6.51); 8.6021 (3.30); 8.5154 (12.22); 8.5128 (11.85); 8.4716 (0.71); 8.4623 (3.85); 8.4599 (3.24); 8.4527 (0.71); 7.7470 (7.69); 7.7340 (9.42); 7.7263 (1.85); 7.7226 (1.18); 7.7167 (1.58); 7.7119 (4.99); 7.6979 (8.94); 7.6909 (1.02); 7.6848 (8.21); 7.6798 (1.16); 7.6750 (1.36); 7.6722 (1.32); 7.6698 (1.47); 7.6327 (5.10); 7.6197 (8.03); 7.6066 (4.02); 7.5920 (0.67); 7.4281 (8.48); 7.4155 (7.71); 5.7556 (3.53); 5.7447 (3.76); 5.2952 (0.61); 5.2843 (1.53); 5.2738 (1.50); 5.2632 (0.59); 5.0565 (6.07); 5.0459 (13.85); 5.0353 (6.18); 4.1466 (1.04); 4.1368 (1.88); 4.1266 (0.99); 4.0928 (0.71); 4.0841 (0.72); 3.9026 (16.00); 3.7770 (2.33); 3.7666 (4.70); 3.7552 (5.92); 3.7445 (8.27); 3.7341 (5.29); 3.7239 (0.88); 3.7124 (0.89); 3.6988 (4.18); 3.6887 (7.05); 3.6784 (5.13); 3.6665 (4.07); 3.6565 (2.38); 3.5088 (0.43); 3.3681 (0.67); 3.3397 (0.63); 3.3171 (689.18); 3.2528 (117.91); 3.2245 (1.99); 3.1722 (2.82); 3.1635 (2.76); 3.1559 (0.60); 3.1327 (0.59); 2.6186 (2.55); 2.6156 (5.43); 2.6126 (7.49); 2.6096 (5.36); 2.6065 (2.45); 2.5402 (1.59); 2.5371 (1.17); 2.5219 (15.43); 2.5188 (19.70); 2.5157 (21.11); 2.5069 (420.79); 2.5039 (890.63); 2.5008 (1223.62); 2.4978 (888.21); 2.4948 (411.55); 2.3911 (2.47); 2.3881 (5.31); 2.3850 (7.32); 2.3820 (5.20); 2.3790 (2.32); 1.6412 (0.40); 1.6313 (0.57); 1.6212 (0.48); 1.3667 (0.74); 1.3605 (0.71); 1.3544 (0.88); 1.3495 (0.87); 1.3433 (0.73); 1.3375 (0.87); 1.3310 (0.38); 1.3252 (0.48); 1.3094 (0.73); 1.2983 (1.17); 1.2896 (1.35); 1.2807 (2.84); 1.2725 (1.79); 1.2585 (0.90); 1.2492 (0.56); 1.2353 (1.12); 0.8881 (2.92); 0.8757 (6.74); 0.8629 (5.73); 0.8507 (1.40); 0.0965 (3.63); 0.0225 (0.38); 0.0052 (32.50); −0.0002 (952.74); −0.0057 (29.02); −0.0204 (0.67); −0.1001 (3.64)

No. Ia-112, Solvent: <[D₆]-DMSO>, Spectrometer: 601.6 MHz

8.9887 (1.73); 8.9869 (1.69); 8.7992 (0.52); 8.7896 (1.07); 8.7800 (0.52); 8.5363 (1.82); 8.5338 (1.80); 7.7743 (1.17); 7.7612 (1.43); 7.7431 (0.58); 7.7305 (1.28); 7.7179 (0.81); 7.6580 (0.76); 7.6453 (1.15); 7.6325 (0.50); 7.4801 (1.25); 7.4675 (1.17); 6.2241 (0.89); 6.2137 (1.93); 6.2032 (0.91); 3.9026 (6.05); 3.7678 (1.45); 3.7576 (2.76); 3.7475 (1.53); 3.3168 (89.87); 3.2338 (0.53); 3.1722 (0.83); 3.1635 (0.81); 2.8902 (0.77); 2.7310 (0.64); 2.7304 (0.62); 2.6186 (0.49); 2.6156 (1.02); 2.6126 (1.43); 2.6095 (1.02); 2.6065 (0.47); 2.5402 (0.37); 2.5219 (2.81); 2.5188 (3.51); 2.5157 (3.50); 2.5069 (75.50); 2.5039 (163.70); 2.5008 (226.40); 2.4977 (165.47); 2.4947 (76.62); 2.3911 (0.43); 2.3881 (0.95); 2.3850 (1.34); 2.3820 (0.94); 2.3789 (0.41); 2.0649 (16.00); 0.0965 (0.75); 0.0053 (6.49); −0.0002 (207.49); −0.0057 (6.19); −0.0112 (0.39); −0.1001 (0.74)

No. Ia-130, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.6046 (7.41); 8.5984 (7.56); 8.5868 (2.07); 8.5730 (3.82); 8.5590 (1.92); 8.3186 (0.67); 7.8642 (5.22); 7.8577 (5.14); 7.8432 (5.90); 7.8367 (5.89); 7.7237 (3.90); 7.7054 (5.17); 7.6580 (1.69); 7.6410 (4.36); 7.6229 (3.59); 7.6046 (3.58); 7.5859 (3.93); 7.5675 (1.36); 7.4291 (7.83); 7.4081 (7.23); 7.3816 (4.66); 7.3780 (6.53); 7.3602 (11.56); 7.3291 (6.92); 7.3109 (11.09); 7.2914 (5.38); 7.2394 (3.87); 7.2362 (2.41); 7.2265 (1.80); 7.2213 (5.14); 7.2034 (1.98); 7.2001 (1.46); 7.1909 (4.67); 7.1728 (4.22); 4.5055 (2.44); 4.4863 (4.81); 4.4667 (2.80); 4.0209 (1.10); 4.0074 (1.26); 4.0001 (1.16); 3.9875 (2.86); 3.9745 (2.10); 3.9672 (2.14); 3.9537 (1.84); 3.9245 (1.95); 3.9042 (16.00); 3.8915 (3.15); 3.8746 (1.57); 3.8589 (1.20); 3.5064 (0.41); 3.4749 (0.39); 3.4328 (0.62); 3.4171 (0.80); 3.3476 (878.83); 3.1746 (0.72); 3.1615 (0.69); 2.8909 (0.33); 2.6767 (1.29); 2.6722 (1.76); 2.6677 (1.33); 2.6634 (0.68); 2.5424 (1.42); 2.5254 (6.09); 2.5119 (100.43); 2.5076 (199.36); 2.5031 (262.29); 2.4986 (196.12); 2.4943 (99.99); 2.3344 (1.21); 2.3298 (1.67); 2.3253 (1.23); 1.2358 (0.56); 0.1460 (0.49); 0.0080 (3.93); −0.0002 (113.14); −0.0084 (4.92); −0.1497 (0.49)

No. Ia-131, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.5906 (5.70); 8.5844 (5.75); 8.4842 (1.51); 8.4702 (2.90); 8.4563 (1.45); 8.3185 (0.38); 7.8649 (3.87); 7.8584 (3.85); 7.8440 (4.25); 7.8376 (4.21); 7.7437 (3.41); 7.7242 (4.55); 7.6973 (1.50); 7.6792 (3.81); 7.6607 (2.71); 7.6239 (2.76); 7.6050 (3.41); 7.5860 (1.22); 7.3523 (4.04); 7.3336 (3.64); 7.3098 (6.13); 7.2889 (5.79); 3.9044 (6.34); 3.8609 (0.58); 3.5428 (0.60); 3.5272 (1.04); 3.5102 (2.46); 3.4933 (4.19); 3.4773 (3.39); 3.4569 (2.50); 3.4387 (1.10); 3.4238 (1.13); 3.3485 (625.63); 3.1679 (0.53); 3.0143 (0.56); 2.9955 (1.23); 2.9784 (1.52); 2.9607 (1.20); 2.9430 (0.52); 2.6767 (0.94); 2.6723 (1.29); 2.6679 (0.97); 2.5424 (0.96); 2.5076 (148.60); 2.5032 (194.96); 2.4989 (148.25); 2.3343 (0.91); 2.3300 (1.23); 2.3256 (0.92); 1.7698 (0.56); 1.7567 (0.90); 1.7517 (0.86); 1.7365 (1.79); 1.7233 (1.48); 1.7176 (1.76); 1.7051 (1.44); 1.6956 (1.65); 1.6769 (1.70); 1.6726 (1.56); 1.6540 (1.52); 1.6432 (0.78); 1.6384 (0.91); 1.6203 (0.61); 1.2355 (0.33); 0.7481 (7.51); 0.7298 (16.00); 0.7113 (7.05); −0.0002 (2.90)

No. Ia-134, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.5462 (11.12); 8.5406 (11.10); 8.5398 (11.10); 8.3185 (1.04); 8.2753 (2.63); 8.2601 (5.36); 8.2449 (2.70); 7.8320 (8.11); 7.8255 (8.06); 7.8107 (9.13); 7.8041 (9.22); 7.7278 (6.43); 7.7083 (8.76); 7.6948 (3.05); 7.6767 (7.36); 7.6581 (5.25); 7.6137 (5.15); 7.5948 (6.58); 7.5757 (2.48); 7.4454 (11.97); 7.4240 (10.87); 7.3676 (7.62); 7.3490 (6.84); 3.9040 (14.31); 3.7076 (0.57); 3.5508 (15.92); 3.5352 (16.00); 3.5065 (0.73); 3.3414 (883.65); 3.2711 (0.52); 3.2537 (0.42); 3.1680 (0.57); 2.6763 (1.74); 2.6717 (2.44); 2.6673 (1.82); 2.5418 (1.18); 2.5251 (6.73); 2.5115 (136.11); 2.5072 (278.03); 2.5027 (372.71); 2.4982 (284.40); 2.4939 (149.41); 2.3339 (1.86); 2.3294 (2.53); 2.3249 (1.93); 2.0557 (1.58); 2.0513 (1.60); 2.0359 (3.17); 2.0194 (5.14); 2.0055 (5.97); 1.9868 (4.11); 1.9586 (3.51); 1.9432 (6.01); 1.9285 (5.70); 1.9123 (3.39); 1.8957 (2.42); 1.8061 (0.70); 1.7939 (0.96); 1.7609 (5.50); 1.7500 (5.62); 1.7333 (3.76); 1.7041 (1.02); 1.6372 (1.13); 1.6073 (3.94); 1.5903 (5.63); 1.5823 (5.03); 1.5698 (3.07); 1.5361 (0.61); 1.2583 (0.36); 1.2356 (1.05); 0.8443 (1.46); 0.8319 (0.71); 0.8216 (0.51); −0.0002 (7.27); −0.0084 (0.33)

No. Ia-139, Solvent: <CDCl₃>, Spectrometer: 399.95 MHz

8.4335 (15.00); 8.4286 (14.43); 7.9358 (0.35); 7.9306 (0.33); 7.8857 (16.00); 7.8806 (15.14); 7.7021 (7.63); 7.6839 (9.09); 7.6488 (0.41); 7.6298 (0.43); 7.6142 (2.47); 7.5968 (7.48); 7.5791 (8.69); 7.5629 (7.19); 7.5440 (9.01); 7.5376 (11.36); 7.5191 (5.73); 7.2622 (8.31); 6.3961 (3.82); 4.5048 (0.47); 4.4884 (6.71); 4.4724 (6.53); 4.4550 (13.60); 4.4391 (13.10); 4.4217 (6.83); 4.4057 (6.61); 4.1302 (0.63); 4.1122 (0.65); 2.0462 (2.67); 1.6193 (1.18); 1.5689 (56.34); 1.5190 (0.44); 1.3024 (0.37); 1.2775 (1.16); 1.2597 (2.46); 1.2421 (0.84); 0.8817 (0.36); 0.0499 (0.57); 0.0003 (28.74); 0.0074 (0.96)

No. Ia-140, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.9225 (5.80); 8.9198 (5.67); 8.4400 (3.51); 8.4297 (6.60); 8.4258 (6.84); 8.4197 (3.92); 7.8525 (4.87); 7.8506 (4.89); 7.8327 (5.27); 7.8309 (5.00); 7.4473 (2.29); 7.4447 (2.29); 7.4369 (0.46); 7.4285 (5.23); 7.4260 (5.05); 7.4098 (3.29); 7.4073 (3.04); 7.2334 (4.31); 7.2296 (4.93); 7.2145 (3.91); 7.2106 (3.91); 7.1650 (2.79); 7.1609 (2.53); 7.1459 (4.26); 7.1420 (3.90); 7.1267 (2.42); 7.1226 (2.14); 4.6110 (0.79); 4.5938 (1.81); 4.5765 (2.08); 4.5737 (2.08); 4.5562 (1.82); 4.5390 (0.80); 3.9051 (1.70); 3.3798 (0.55); 3.3440 (240.69); 3.2456 (0.37); 3.2264 (0.41); 3.2078 (5.64); 3.1908 (6.06); 3.1718 (0.70); 3.1544 (0.34); 2.6768 (0.40); 2.6724 (0.54); 2.6684 (0.42); 2.5427 (0.46); 2.5257 (1.67); 2.5121 (31.82); 2.5078 (62.50); 2.5033 (81.97); 2.4988 (61.27); 2.4945 (30.93); 2.3345 (0.40); 2.3301 (0.55); 2.3254 (0.41); 1.2187 (16.00); 1.2019 (15.91); 0.0080 (1.69); −0.0002 (48.66); −0.0085 (1.95)

No. Ia-141, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.8990 (5.34); 8.8964 (5.32); 8.4834 (2.91); 8.4622 (2.94); 8.4236 (5.49); 8.4198 (5.36); 8.3178 (0.61); 7.4597 (1.67); 7.4558 (2.43); 7.4399 (4.96); 7.4363 (5.97); 7.4304 (2.77); 7.4259 (2.79); 7.4130 (4.29); 7.4084 (4.13); 7.3938 (2.12); 7.3876 (3.61); 7.3825 (2.32); 7.3686 (4.15); 7.3645 (4.18); 7.3510 (2.19); 7.3470 (2.08); 7.3233 (4.77); 7.3196 (4.18); 7.3052 (2.84); 7.3005 (2.29); 4.6432 (0.68); 4.6246 (1.47); 4.6072 (1.96); 4.5873 (1.44); 4.5704 (0.71); 3.9040 (5.33); 3.5083 (0.36); 3.4618 (0.48); 3.3500 (780.94); 3.2887 (0.38); 3.2821 (0.36); 3.2319 (0.67); 3.2158 (0.85); 3.1974 (3.64); 3.1833 (5.39); 3.1659 (3.45); 3.1505 (0.74); 3.1310 (0.71); 2.6770 (1.01); 2.6725 (1.40); 2.6680 (1.07); 2.5257 (4.84); 2.5122 (82.88); 2.5080 (164.24); 2.5035 (215.96); 2.4990 (163.69); 2.4949 (85.43); 2.3346 (0.99); 2.3303 (1.35); 2.3258 (1.03); 1.3504 (0.81); 1.3357 (0.44); 1.2976 (0.44); 1.2584 (0.71); 1.2490 (0.68); 1.2319 (4.97); 1.2245 (16.00); 1.2077 (15.18); 0.1459 (0.33); 0.0079 (2.65); −0.0002 (76.85); −0.0084 (3.51); −0.1496 (0.35)

No. Ia-142, Solvent: <CDCl₃>, Spectrometer: 399.95 MHz

8.4650 (9.39); 8.4599 (9.26); 7.8820 (10.40); 7.8768 (10.81); 7.8715 (8.62); 7.8518 (7.67); 7.4341 (0.32); 7.3845 (16.00); 7.3831 (15.33); 7.3727 (14.19); 7.3531 (0.59); 7.2616 (21.64); 7.1372 (0.67); 7.1283 (3.64); 7.1174 (4.90); 7.1083 (4.06); 7.1054 (3.40); 7.0982 (3.77); 7.0957 (3.15); 7.0855 (2.92); 7.0763 (0.37); 6.3489 (2.26); 4.4928 (4.48); 4.4767 (4.23); 4.4594 (9.24); 4.4433 (8.95); 4.4260 (4.66); 4.4099 (4.50); 2.0467 (0.46); 1.6063 (2.16); 1.5565 (156.08); 1.5063 (1.18); 1.2600 (1.50); 0.8981 (0.36); 0.8818 (0.84); 0.8640 (0.42); 0.0692 (0.47); 0.0496 (0.84); 0.0078 (2.84); 0.0003 (67.58); 0.0085 (2.21); 0.0504 (0.47)

No. Ia-143, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

9.0182 (6.34); 9.0154 (6.20); 8.9462 (2.28); 8.9435 (2.23); 8.5984 (3.78); 8.5759 (3.83); 8.4682 (6.60); 8.4645 (6.48); 8.4248 (2.35); 8.4211 (2.35); 8.3084 (1.33); 8.2861 (1.34); 7.7964 (4.07); 7.7758 (6.05); 7.7536 (4.60); 7.7349 (3.10); 7.7233 (1.58); 7.7034 (1.93); 7.6900 (0.73); 7.6720 (4.51); 7.6530 (5.07); 7.6337 (1.59); 7.6165 (1.14); 7.5974 (1.37); 7.5782 (0.50); 7.5215 (4.61); 7.5028 (3.99); 7.2237 (1.59); 7.2051 (1.47); 4.4982 (0.51); 4.4803 (0.83); 4.4589 (0.95); 4.4489 (1.22); 4.4412 (1.16); 4.4319 (1.33); 4.4257 (2.04); 4.4093 (1.98); 4.4031 (1.34); 4.3861 (1.07); 3.9050 (4.43); 3.7905 (0.59); 3.7795 (0.84); 3.7722 (1.82); 3.7639 (2.30); 3.7462 (2.83); 3.7390 (2.63); 3.7217 (1.39); 3.7130 (1.30); 3.5082 (0.40); 3.4742 (0.41); 3.4338 (0.91); 3.3509 (631.09); 2.6774 (0.85); 2.6730 (1.17); 2.6687 (0.94); 2.5433 (1.31); 2.5262 (4.07); 2.5128 (67.28); 2.5084 (132.47); 2.5039 (174.70); 2.4994 (130.98); 2.4950 (66.06); 2.3352 (0.79); 2.3307 (1.09); 2.3261 (0.78); 1.8760 (1.05); 1.8611 (1.11); 1.8429 (1.92); 1.8274 (1.78); 1.8162 (1.74); 1.8005 (1.50); 1.6952 (1.31); 1.6866 (1.57); 1.6778 (1.50); 1.6688 (1.60); 1.6619 (1.32); 1.6531 (1.10); 1.6435 (1.21); 1.6346 (1.05); 1.6241 (0.60); 1.6129 (0.58); 1.6059 (0.59); 1.5943 (0.64); 1.5797 (0.43); 1.5715 (0.47); 1.5616 (0.39); 1.2585 (0.37); 1.2491 (0.47); 1.2355 (0.69); 1.1652 (5.70); 1.1483 (5.69); 0.8893 (16.00); 0.8727 (15.96); 0.8343 (0.45); 0.8128 (0.39); 0.4165 (0.43); 0.3989 (0.65); 0.3810 (0.53); 0.3373 (0.54); 0.3256 (1.23); 0.3040 (2.09); 0.2923 (2.93); 0.2811 (2.62); 0.2713 (3.00); 0.2610 (2.50); 0.2494 (1.84); 0.2271 (0.85); 0.2126 (0.60); 0.2030 (0.82); 0.1929 (0.86); 0.1847 (1.46); 0.1719 (1.73); 0.1621 (2.28); 0.1529 (2.03); 0.1430 (1.82); 0.1334 (0.83); 0.1299 (0.86); 0.1198 (0.64); 0.0239 (0.43); 0.0080 (3.07); −0.0002 (77.98); −0.0086 (4.19); −0.0219 (2.21); −0.0336 (2.67); −0.0445 (2.43); −0.0552 (1.60); −0.0672 (0.70); −0.1497 (0.35); −0.2507 (0.69); −0.2610 (0.97); −0.2731 (0.90); −0.2836 (0.56); −0.3358 (0.83); −0.3478 (1.84); −0.3584 (2.64); −0.3705 (2.52); −0.3811 (1.59); −0.3934 (0.65)

No. Ia-144, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

9.0148 (6.47); 9.0122 (6.38); 8.9501 (2.71); 8.6572 (3.88); 8.6346 (3.92); 8.4527 (6.79); 8.4488 (6.66); 8.4142 (2.80); 8.4104 (2.75); 8.3541 (1.57); 8.3322 (1.57); 8.3178 (0.91); 7.8446 (0.52); 7.8251 (0.73); 7.8020 (4.48); 7.7822 (6.08); 7.7575 (5.02); 7.7386 (3.68); 7.7260 (2.01); 7.7062 (2.50); 7.6961 (1.03); 7.6774 (4.93); 7.6584 (5.38); 7.6394 (1.62); 7.6189 (1.37); 7.5999 (1.66); 7.5806 (0.70); 7.5644 (4.83); 7.5456 (4.08); 7.2520 (1.87); 7.2334 (1.73); 5.6333 (0.53); 5.6258 (0.45); 5.6143 (0.96); 5.6087 (1.03); 5.5910 (1.57); 5.5716 (1.52); 5.5467 (1.49); 5.5273 (1.34); 5.5109 (0.81); 4.8985 (1.57); 4.8611 (2.14); 4.8415 (1.69); 4.8218 (8.38); 4.7922 (4.18); 4.7841 (3.68); 4.5076 (0.61); 4.4902 (1.16); 4.4706 (1.71); 4.4542 (2.58); 4.4375 (2.31); 4.4153 (1.17); 4.3981 (0.35); 3.9042 (10.96); 3.7700 (0.72); 3.7563 (2.00); 3.7461 (2.33); 3.7307 (3.13); 3.7225 (2.66); 3.7071 (1.73); 3.6973 (1.46); 3.5079 (0.64); 3.4806 (0.88); 3.3506 (1539.96); 3.1747 (0.47); 3.1615 (0.38); 2.6769 (2.71); 2.6724 (3.49); 2.6681 (3.03); 2.6456 (2.15); 2.6348 (1.87); 2.6195 (2.28); 2.5989 (2.90); 2.5734 (3.11); 2.5576 (2.26); 2.5078 (314.33); 2.5034 (415.06); 2.4990 (317.53); 2.3345 (1.98); 2.3301 (2.73); 2.3258 (2.07); 1.2573 (0.38); 1.2354 (1.00); 1.1947 (6.71); 1.1777 (6.67); 0.9275 (15.94); 0.9109 (16.00); 0.8543 (0.50); 0.8349 (0.38); 0.0080 (1.12); −0.0002 (34.56); −0.0082 (1.78)

No. Ia-146, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

9.0142 (6.23); 9.0116 (6.15); 8.9482 (2.09); 8.9457 (2.07); 8.5225 (3.77); 8.4998 (3.90); 8.4605 (6.55); 8.4565 (6.53); 8.4135 (2.13); 8.4093 (2.19); 8.3184 (0.92); 8.2788 (1.23); 8.2567 (1.24); 7.5093 (3.45); 7.4903 (7.03); 7.4754 (0.52); 7.4671 (2.06); 7.4558 (4.52); 7.4445 (4.20); 7.4365 (2.70); 7.4253 (3.89); 7.4113 (15.73); 7.4015 (8.21); 7.3900 (1.78); 7.3858 (1.60); 7.3701 (0.69); 7.3662 (0.76); 7.3560 (1.18); 7.3519 (1.39); 7.3395 (3.06); 7.3337 (1.50); 7.3207 (0.68); 7.3164 (0.64); 7.2010 (1.51); 7.1830 (1.25); 7.1790 (1.17); 7.1428 (0.41); 7.1210 (0.45); 6.8656 (0.51); 6.8446 (0.44); 4.5472 (1.59); 4.4999 (0.42); 4.4816 (0.99); 4.4648 (1.57); 4.4423 (2.44); 4.4257 (2.12); 4.4200 (1.38); 4.4027 (1.12); 4.1062 (0.45); 4.0962 (0.54); 4.0844 (0.45); 3.9041 (14.00); 3.8000 (0.48); 3.7891 (0.62); 3.7719 (1.98); 3.7635 (2.13); 3.7461 (3.00); 3.7390 (2.70); 3.7221 (1.41); 3.7136 (1.29); 3.5958 (2.06); 3.5070 (0.34); 3.4478 (0.40); 3.4332 (0.55); 3.3426 (1142.35); 3.3072 (1.35); 3.1742 (0.43); 3.1616 (0.47); 2.6765 (1.85); 2.6722 (2.55); 2.6678 (1.90); 2.5420 (1.67); 2.5253 (7.87); 2.5075 (293.89); 2.5031 (387.92); 2.4987 (294.83); 2.3342 (1.83); 2.3298 (2.51); 2.3257 (1.90); 1.9533 (0.47); 1.8934 (0.89); 1.8787 (1.27); 1.8607 (1.93); 1.8519 (1.58); 1.8447 (2.00); 1.8338 (1.80); 1.8182 (1.75); 1.8021 (0.54); 1.7372 (1.44); 1.7285 (1.69); 1.7195 (1.63); 1.7110 (1.76); 1.7041 (1.39); 1.6950 (1.14); 1.6853 (1.24); 1.6765 (1.07); 1.6312 (0.52); 1.6209 (0.61); 1.6130 (0.59); 1.6023 (0.64); 1.5868 (0.44); 1.5792 (0.48); 1.5683 (0.44); 1.3237 (4.19); 1.2987 (0.39); 1.2585 (0.71); 1.2352 (1.57); 1.1783 (5.21); 1.1614 (5.23); 0.9074 (15.90); 0.8908 (16.00); 0.8541 (0.68); 0.8348 (0.56); 0.8110 (0.45); 0.3987 (0.60); 0.3812 (0.51); 0.3619 (0.33); 0.3419 (0.57); 0.3234 (1.27); 0.3117 (2.04); 0.3032 (2.12); 0.2946 (2.97); 0.2827 (2.73); 0.2736 (2.93); 0.2638 (2.47); 0.2517 (2.00); 0.2301 (0.79); 0.2128 (0.64); 0.2026 (0.81); 0.1890 (1.48); 0.1786 (1.82); 0.1757 (1.81); 0.1657 (2.30); 0.1566 (2.17); 0.1462 (1.88); 0.1335 (0.97); 0.1237 (0.73); 0.0113 (0.68); −0.0002 (6.98); −0.0088 (1.80); −0.0207 (2.12); −0.0309 (2.64); −0.0419 (2.71); −0.0529 (1.74); −0.0646 (0.80); −0.2481 (0.65); −0.2586 (0.88); −0.2705 (0.84); −0.2818 (0.55); −0.3254 (0.82); −0.3372 (1.89); −0.3481 (2.68); −0.3600 (2.61); −0.3711 (1.68); −0.3829 (0.74)

No. Ia-148, Solvent: <CDCl₃>, Spectrometer: 399.95 MHz

12.1118 (0.35); 8.7402 (14.50); 8.1121 (15.45); 8.1081 (14.80); 7.7497 (0.34); 7.7007 (8.47); 7.6990 (8.09); 7.6821 (10.13); 7.6799 (9.91); 7.6350 (0.37); 7.6191 (2.60); 7.6163 (2.70); 7.6004 (8.15); 7.5990 (7.85); 7.5826 (9.85); 7.5790 (7.73); 7.5664 (8.00); 7.5495 (8.37); 7.5479 (8.24); 7.5346 (13.14); 7.5329 (12.31); 7.5180 (5.94); 7.5163 (6.36); 7.5151 (6.18); 7.2665 (5.62); 7.2652 (4.92); 6.4220 (4.29); 5.3030 (1.17); 5.3017 (1.06); 4.5320 (7.56); 4.5159 (7.44); 4.4986 (16.00); 4.4825 (15.56); 4.4651 (8.14); 4.4490 (7.86); 3.1322 (2.22); 3.1201 (2.53); 3.1140 (6.90); 3.1019 (7.07); 3.0956 (7.14); 3.0836 (6.95); 3.0773 (2.59); 3.0652 (2.32); 1.6283 (12.44); 1.4506 (0.34); 1.4316 (14.62); 1.4133 (29.08); 1.3949 (13.80); 1.2600 (0.52); 1.1402 (0.36); 1.1247 (0.36); 0.0070 (0.52); 0.0001 (9.53); 0.0011 (8.75); 0.0084 (0.32)

No. Ia-149, Solvent: <CDCl₃>, Spectrometer: 399.95 MHz

8.4128 (0.38); 8.3052 (5.56); 8.2999 (5.51); 8.2711 (12.61); 8.2655 (12.40); 8.1285 (0.33); 8.1235 (0.37); 7.8650 (3.06); 7.8627 (2.95); 7.8453 (3.20); 7.8430 (2.98); 7.8259 (6.27); 7.8230 (6.17); 7.8058 (6.43); 7.8033 (6.73); 7.7201 (0.44); 7.7084 (16.00); 7.7030 (14.65); 7.6616 (7.36); 7.6563 (6.59); 7.5300 (0.38); 7.5242 (0.41); 7.4276 (1.14); 7.4226 (1.63); 7.4086 (4.01); 7.4036 (3.92); 7.3969 (2.83); 7.3943 (2.60); 7.3880 (0.64); 7.3792 (2.89); 7.3765 (2.92); 7.3603 (1.27); 7.3575 (1.27); 7.3516 (3.29); 7.3489 (3.25); 7.3328 (7.04); 7.3301 (7.11); 7.3142 (4.58); 7.3113 (4.76); 7.2640 (7.84); 7.2558 (0.49); 7.2455 (0.34); 7.1922 (6.37); 7.1881 (6.94); 7.1732 (5.47); 7.1689 (5.38); 7.1252 (3.28); 7.1200 (3.21); 7.1073 (3.32); 7.1054 (3.66); 7.1023 (3.12); 7.1004 (3.09); 7.0878 (5.90); 7.0835 (4.55); 7.0684 (5.39); 7.0641 (5.02); 7.0496 (3.54); 7.0453 (3.35); 6.0486 (1.15); 5.3029 (4.65); 4.0587 (1.41); 4.0444 (1.79); 4.0393 (4.03); 4.0251 (4.45); 4.0199 (4.36); 4.0057 (4.23); 4.0006 (1.74); 3.9864 (1.54); 3.4701 (0.38); 3.4556 (0.40); 3.4484 (0.73); 3.4393 (1.10); 3.4364 (1.03); 3.4287 (1.60); 3.4199 (1.63); 3.4175 (1.00); 3.4124 (0.97); 3.4085 (1.12); 3.4004 (0.78); 2.9428 (2.59); 2.9265 (3.20); 2.9237 (2.99); 2.9204 (3.21); 2.9075 (3.21); 2.9041 (3.23); 2.9013 (3.09); 2.8850 (2.69); 2.8073 (1.12); 2.7995 (1.13); 2.7924 (1.28); 2.7843 (2.31); 2.7765 (1.28); 2.7691 (1.24); 2.7614 (1.22); 1.7678 (1.40); 1.7529 (1.85); 1.7487 (1.61); 1.7397 (1.61); 1.7354 (1.81); 1.7339 (1.83); 1.7205 (1.45); 1.6272 (2.78); 1.6131 (3.94); 1.6074 (3.42); 1.6048 (3.57); 1.5978 (26.24); 1.5936 (5.45); 1.5909 (4.57); 1.5849 (2.93); 1.5709 (3.39); 1.5407 (3.53); 1.5265 (6.62); 1.5105 (6.34); 1.4963 (2.49); 1.4779 (1.57); 1.4652 (2.38); 1.4545 (1.86); 1.4421 (2.35); 1.4295 (1.34); 1.2526 (0.50); 1.1400 (0.44); 1.1250 (0.50); 0.9871 (0.57); 0.9690 (1.11); 0.9507 (0.52); 0.0701 (0.44); 0.0079 (0.46); 0.0001 (15.35); 0.0086 (0.54)

No. Ia-150, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

11.1731 (1.33); 9.0841 (12.31); 8.9033 (3.70); 8.8879 (7.50); 8.8723 (3.60); 8.7050 (12.28); 8.3192 (1.25); 7.9894 (0.94); 7.9699 (1.00); 7.8724 (10.64); 7.8528 (10.82); 7.7116 (0.68); 7.6926 (0.80); 7.4949 (0.65); 7.4751 (1.21); 7.4594 (5.22); 7.4428 (9.78); 7.4407 (10.56); 7.4242 (6.04); 7.4219 (6.34); 7.2494 (8.81); 7.2456 (10.46); 7.2304 (8.32); 7.2266 (8.52); 7.1903 (5.35); 7.1862 (5.12); 7.1711 (8.53); 7.1672 (8.25); 7.1520 (4.57); 7.1479 (4.24); 4.3075 (3.68); 4.2918 (3.75); 4.2717 (8.18); 4.2561 (7.95); 4.2358 (4.19); 4.2202 (3.92); 3.9043 (16.00); 3.8516 (0.57); 3.8407 (1.96); 3.8129 (0.36); 3.7487 (0.54); 3.7391 (0.43); 3.7265 (0.39); 3.6394 (0.43); 3.6268 (0.50); 3.6159 (0.41); 3.6034 (0.93); 3.5074 (0.47); 3.3387 (1026.61); 3.1742 (0.54); 3.1612 (0.58); 3.0696 (0.43); 3.0443 (0.87); 2.6762 (2.98); 2.6718 (4.12); 2.6674 (3.18); 2.6340 (0.35); 2.5248 (14.13); 2.5111 (232.92); 2.5072 (460.71); 2.5027 (612.49); 2.4983 (472.74); 2.3338 (2.78); 2.3295 (3.90); 2.3250 (3.00); 2.0454 (0.51); 1.8055 (0.53); 1.2583 (0.49); 1.2348 (1.42); 1.1757 (0.43); 0.9940 (0.33); 0.8531 (0.40); 0.8333 (0.36); 0.8113 (0.33); 0.1459 (1.11); 0.0079 (9.33); −0.0002 (254.08); −0.0083 (14.39); −0.1497 (1.17)

No. Ia-153, Solvent: <[D₆]-DMSO>, Spectrometer: 601.6 MHz

8.9083 (5.11); 8.9065 (4.94); 8.4567 (2.74); 8.4426 (2.78); 8.4208 (5.30); 8.4180 (5.17); 7.6128 (4.22); 7.6114 (4.38); 7.5995 (4.66); 7.5981 (4.67); 7.4243 (1.86); 7.4226 (1.95); 7.4119 (4.63); 7.4102 (4.68); 7.3995 (3.15); 7.3978 (3.05); 7.3413 (2.52); 7.3384 (2.95); 7.3283 (3.35); 7.3254 (3.80); 7.3156 (1.92); 7.3127 (1.98); 7.2914 (4.60); 7.2886 (4.08); 7.2790 (3.86); 7.2761 (3.36); 4.6202 (0.74); 4.6087 (1.66); 4.5971 (1.91); 4.5951 (1.83); 4.5834 (1.65); 4.5719 (0.76); 3.9026 (6.07); 3.3171 (223.65); 3.1949 (7.63); 3.1831 (6.86); 3.1722 (1.05); 3.1635 (0.89); 2.6185 (1.04); 2.6156 (2.08); 2.6126 (2.85); 2.6096 (2.08); 2.6066 (1.01); 2.5403 (0.83); 2.5372 (0.68); 2.5219 (6.48); 2.5188 (8.19); 2.5157 (9.01); 2.5068 (160.09); 2.5039 (331.73); 2.5009 (452.12); 2.4978 (329.79); 2.4949 (153.83); 2.4782 (0.36); 2.4749 (0.32); 2.3910 (0.90); 2.3880 (1.95); 2.3850 (2.69); 2.3820 (1.91); 2.3791 (0.82); 1.5476 (0.39); 1.5366 (0.37); 1.2882 (0.36); 1.2771 (0.38); 1.2361 (0.39); 1.2171 (16.00); 1.2060 (15.94); 0.0965 (1.35); 0.0052 (12.24); −0.0002 (325.94); −0.0057 (9.64); −0.1001 (1.33)

No. Ia-154, Solvent: <[D₆]-DMSO>, Spectrometer: 601.6 MHz

8.8555 (5.44); 8.6307 (2.84); 8.6166 (2.88); 8.4223 (5.65); 8.4195 (5.52); 7.6722 (1.94); 7.6649 (2.57); 7.6572 (3.20); 7.6175 (0.95); 7.6093 (6.69); 7.6051 (4.23); 7.6010 (4.49); 7.5942 (6.40); 7.5860 (0.66); 7.5175 (2.72); 7.5101 (2.57); 7.5030 (1.90); 7.0726 (2.06); 6.9801 (4.50); 6.8874 (2.26); 4.6398 (0.61); 4.6262 (1.34); 4.6156 (1.78); 4.6049 (1.33); 4.5913 (0.61); 3.9026 (3.58); 3.3209 (181.50); 3.2624 (1.73); 3.2529 (1.79); 3.2394 (2.85); 3.2299 (2.69); 3.1750 (2.88); 3.1612 (2.83); 3.1522 (1.80); 3.1383 (1.76); 2.6159 (1.79); 2.6129 (2.44); 2.6100 (1.75); 2.6071 (0.83); 2.5405 (0.48); 2.5221 (4.59); 2.5191 (5.85); 2.5160 (6.45); 2.5070 (142.10); 2.5041 (292.87); 2.5012 (399.12); 2.4982 (293.67); 2.4954 (140.67); 2.3911 (0.81); 2.3883 (1.71); 2.3854 (2.33); 2.3824 (1.68); 1.9083 (0.77); 1.2597 (15.95); 1.2485 (16.00); 0.0966 (1.23); 0.0150 (0.36); 0.0051 (9.69); −0.0002 (255.35); −0.0055 (8.45); −0.1000 (1.23)

No. Ia-155, Solvent: <[D₆]-DMSO>, Spectrometer: 601.6 MHz

9.0356 (2.97); 9.0336 (2.88); 8.9848 (1.48); 8.9829 (1.43); 8.5686 (1.85); 8.5537 (1.88); 8.4968 (3.17); 8.4940 (3.14); 8.4490 (1.50); 8.4462 (1.48); 8.3871 (0.40); 8.3128 (0.86); 8.2983 (0.88); 7.6666 (2.50); 7.6653 (2.60); 7.6533 (2.77); 7.6520 (2.77); 7.6444 (0.33); 7.6422 (0.40); 7.6289 (0.45); 7.5974 (1.22); 7.5959 (1.26); 7.5841 (1.37); 7.5826 (1.34); 7.4662 (0.88); 7.4645 (0.88); 7.4538 (2.41); 7.4523 (2.37); 7.4418 (2.42); 7.4401 (2.35); 7.4280 (2.82); 7.4248 (3.49); 7.4155 (1.68); 7.4122 (1.43); 7.4070 (0.77); 7.4051 (0.69); 7.3944 (1.41); 7.3927 (1.37); 7.3821 (2.56); 7.3791 (1.77); 7.3690 (2.02); 7.3668 (1.72); 7.3658 (1.73); 7.3570 (1.45); 7.3536 (1.56); 7.3506 (0.52); 7.3410 (0.56); 7.3380 (0.36); 7.3307 (0.89); 7.3279 (0.93); 7.3178 (1.03); 7.3149 (1.07); 7.3050 (0.57); 7.3021 (0.58); 7.1939 (1.16); 7.1911 (1.16); 7.1815 (1.08); 7.1786 (1.01); 6.9987 (0.51); 6.9696 (0.56); 4.4933 (0.34); 4.4814 (0.56); 4.4672 (0.56); 4.4553 (0.36); 4.4181 (0.58); 4.4145 (0.38); 4.4067 (0.65); 4.4032 (1.13); 4.3920 (1.12); 4.3884 (0.68); 4.3773 (0.64); 4.0931 (0.33); 4.0843 (0.34); 3.9025 (16.00); 3.8959 (0.51); 3.8905 (0.46); 3.8861 (1.17); 3.8793 (1.10); 3.8714 (0.92); 3.8679 (1.18); 3.8651 (1.07); 3.8615 (0.87); 3.8534 (0.76); 3.8466 (0.70); 3.8320 (0.42); 3.3451 (0.36); 3.3174 (340.37); 3.1722 (1.32); 3.1635 (1.31); 2.8902 (2.45); 2.8379 (0.67); 2.8334 (0.82); 2.8313 (0.88); 2.8268 (0.75); 2.8101 (1.24); 2.8057 (1.40); 2.7991 (1.04); 2.7920 (0.39); 2.7857 (0.55); 2.7815 (0.58); 2.7686 (0.53); 2.7643 (0.56); 2.7306 (2.10); 2.7265 (1.05); 2.7221 (1.16); 2.7145 (0.73); 2.7117 (0.82); 2.7079 (1.42); 2.7040 (1.15); 2.6989 (0.76); 2.6944 (0.84); 2.6869 (0.50); 2.6804 (0.91); 2.6764 (0.82); 2.6421 (1.14); 2.6378 (2.23); 2.6335 (1.13); 2.6301 (2.33); 2.6258 (4.49); 2.6214 (2.04); 2.6187 (1.51); 2.6156 (2.75); 2.6126 (3.76); 2.6096 (2.72); 2.6066 (1.30); 2.5701 (0.33); 2.5402 (1.04); 2.5371 (0.89); 2.5219 (7.48); 2.5188 (9.25); 2.5157 (10.08); 2.5069 (200.87); 2.5039 (426.09); 2.5008 (586.76); 2.4978 (430.22); 2.4948 (201.99); 2.4749 (0.44); 2.3911 (1.16); 2.3880 (2.51); 2.3850 (3.47); 2.3820 (2.47); 2.3791 (1.11); 2.0349 (0.67); 1.9081 (1.99); 1.5019 (0.96); 1.4905 (0.94); 1.3550 (1.78); 1.2368 (0.55); 1.1785 (3.96); 1.1671 (3.95); 1.1039 (0.39); 1.0934 (0.38); 1.0336 (0.35); 1.0223 (0.35); 0.9666 (8.39); 0.9554 (8.40); 0.0965 (1.58); 0.0052 (12.30); −0.0002 (385.32); −0.0057 (12.48); −0.1001 (1.59)

No. Ia-156, Solvent: <[D₆]-DMSO>, Spectrometer: 601.6 MHz

9.0101 (5.83); 9.0081 (5.82); 8.9980 (2.67); 8.9960 (2.65); 8.6976 (3.45); 8.6827 (3.53); 8.5010 (6.06); 8.4982 (6.05); 8.4471 (1.52); 8.4356 (3.24); 8.4328 (4.10); 8.3932 (0.47); 7.7377 (0.53); 7.7312 (0.55); 7.7186 (2.22); 7.7125 (2.80); 7.7107 (2.99); 7.7042 (3.39); 7.6990 (1.17); 7.6893 (0.51); 7.6808 (0.38); 7.6604 (0.53); 7.6547 (1.94); 7.6492 (6.23); 7.6435 (6.56); 7.6389 (7.17); 7.6338 (13.74); 7.6300 (6.83); 7.6229 (2.57); 7.6208 (2.26); 7.6133 (1.10); 7.6090 (1.05); 7.6045 (0.99); 7.5958 (2.95); 7.5922 (2.31); 7.5875 (2.71); 7.5836 (1.64); 7.5806 (2.71); 7.5718 (0.43); 7.4239 (1.20); 7.4160 (1.23); 7.4095 (0.96); 7.3266 (2.17); 7.2424 (0.53); 7.2339 (5.19); 7.1413 (2.45); 7.0524 (0.98); 7.0031 (0.57); 6.9683 (0.72); 6.9597 (2.20); 6.8671 (1.10); 4.5365 (0.59); 4.5247 (0.94); 4.5102 (0.93); 4.4985 (0.63); 4.4896 (0.35); 4.4788 (1.09); 4.4645 (2.08); 4.4531 (2.09); 4.4388 (1.20); 4.4272 (0.35); 4.0928 (0.70); 4.0841 (0.72); 3.9390 (1.34); 3.9262 (3.38); 3.9127 (3.23); 3.9026 (14.71); 3.8954 (0.79); 3.8877 (0.77); 3.8830 (0.70); 3.8785 (0.82); 3.8756 (0.85); 3.8710 (0.72); 3.8664 (0.67); 3.8586 (0.62); 3.8320 (0.61); 3.8256 (0.47); 3.3928 (0.38); 3.3837 (0.40); 3.3171 (427.45); 3.2943 (0.33); 3.1723 (2.63); 3.1636 (2.55); 2.8902 (1.49); 2.8003 (0.60); 2.7961 (0.63); 2.7833 (0.70); 2.7792 (0.67); 2.7726 (1.02); 2.7684 (1.11); 2.7632 (0.45); 2.7559 (0.96); 2.7516 (1.04); 2.7304 (1.68); 2.7222 (5.24); 2.7180 (5.88); 2.7097 (6.05); 2.7057 (5.90); 2.6865 (0.65); 2.6821 (0.84); 2.6791 (0.64); 2.6745 (0.70); 2.6548 (1.98); 2.6505 (3.79); 2.6462 (1.56); 2.6340 (4.29); 2.6298 (8.45); 2.6255 (3.49); 2.6186 (2.08); 2.6156 (4.12); 2.6126 (5.64); 2.6096 (4.15); 2.6066 (2.07); 2.5922 (0.33); 2.5868 (0.35); 2.5703 (0.46); 2.5479 (1.41); 2.5403 (1.64); 2.5371 (1.08); 2.5219 (11.27); 2.5188 (15.59); 2.5158 (14.35); 2.5069 (297.70); 2.5039 (635.76); 2.5009 (882.93); 2.4979 (649.72); 2.4949 (308.19); 2.3911 (1.69); 2.3881 (3.75); 2.3851 (5.21); 2.3820 (3.75); 2.3791 (1.72); 2.0329 (1.17); 1.9082 (2.25); 1.5226 (1.09); 1.5110 (1.11); 1.4253 (0.68); 1.4148 (0.66); 1.3551 (1.93); 1.3480 (0.49); 1.2584 (0.44); 1.2492 (0.50); 1.2368 (1.03); 1.2100 (6.90); 1.1986 (6.84); 1.1692 (0.35); 1.1574 (0.35); 1.1171 (0.45); 1.1049 (0.41); 1.0999 (0.35); 1.0919 (0.47); 1.0835 (0.62); 1.0723 (0.54); 1.0023 (15.91); 0.9910 (16.00); 0.8857 (0.37); 0.8753 (0.41); 0.8541 (0.46); 0.8496 (0.41); 0.8377 (0.34); 0.0965 (2.60); 0.0052 (19.58); −0.0002 (622.08); −0.0057 (21.19); −0.0229 (0.38); −0.1001 (2.59)

No. Ia-157, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.9161 (2.44); 8.9134 (2.43); 8.4066 (2.54); 8.4026 (2.54); 8.3194 (0.38); 8.1660 (0.72); 8.1516 (1.38); 8.1394 (0.63); 7.4632 (0.59); 7.4598 (0.62); 7.4415 (1.52); 7.4259 (1.36); 7.4225 (1.35); 7.3789 (2.42); 7.3621 (2.03); 7.3465 (1.83); 7.3285 (1.04); 7.3254 (0.97); 7.2769 (2.12); 7.2607 (1.29); 7.2582 (1.27); 6.9653 (3.16); 6.9613 (4.81); 6.9412 (3.49); 6.8907 (2.08); 6.8857 (1.89); 6.8701 (1.24); 6.8651 (1.15); 3.9043 (10.96); 3.7696 (16.00); 3.7474 (15.83); 3.4839 (0.52); 3.4625 (0.72); 3.4555 (1.09); 3.4407 (0.96); 3.4247 (1.07); 3.4088 (1.24); 3.3930 (0.82); 3.3421 (236.37); 3.1678 (0.75); 2.6764 (0.71); 2.6720 (0.97); 2.6677 (0.72); 2.5422 (0.78); 2.5251 (3.31); 2.5074 (120.85); 2.5029 (157.12); 2.4985 (119.23); 2.3342 (0.70); 2.3297 (0.96); 2.3251 (0.73); 1.5826 (0.42); 1.5671 (0.61); 1.5478 (0.75); 1.5285 (0.54); 1.5021 (0.47); 1.4903 (0.55); 1.4838 (0.56); 1.4711 (0.66); 1.4562 (0.41); 1.4511 (0.40); 0.6361 (2.94); 0.6178 (6.36); 0.5993 (2.78); −0.0002 (2.26)

No. Ia-161, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.8663 (9.30); 8.8638 (9.53); 8.7395 (5.78); 8.7369 (5.94); 8.3408 (6.05); 8.3364 (6.10); 8.3187 (1.49); 8.3083 (10.01); 8.3043 (10.09); 8.1596 (5.73); 8.1377 (5.90); 7.9539 (3.11); 7.9311 (3.18); 7.5737 (12.55); 7.5561 (15.19); 7.5526 (12.67); 7.5203 (7.44); 7.5030 (9.49); 7.4993 (8.55); 7.4784 (1.57); 7.4659 (1.23); 7.4598 (4.83); 7.4542 (2.68); 7.4508 (2.97); 7.4453 (3.23); 7.4417 (4.35); 7.4385 (3.95); 7.4323 (8.11); 7.4272 (2.86); 7.4174 (3.94); 7.4142 (6.47); 7.4003 (7.84); 7.3813 (10.18); 7.3736 (12.70); 7.3638 (4.93); 7.3545 (16.00); 7.3368 (5.95); 4.7201 (1.60); 4.7119 (1.82); 4.6983 (1.85); 4.6889 (1.67); 4.4259 (0.70); 4.4159 (0.83); 4.3967 (2.03); 4.3679 (2.10); 4.3491 (0.94); 4.3386 (0.78); 3.9044 (14.38); 3.6454 (1.19); 3.6370 (2.25); 3.6285 (1.46); 3.6163 (1.43); 3.6081 (2.40); 3.5995 (1.41); 3.5857 (1.80); 3.5779 (1.91); 3.5571 (3.44); 3.5492 (3.27); 3.5297 (1.96); 3.5210 (1.78); 3.4731 (0.36); 3.4545 (0.40); 3.4376 (0.40); 3.4305 (0.52); 3.4159 (0.73); 3.3460 (1897.15); 3.2820 (1.56); 3.2468 (0.81); 3.2297 (0.61); 3.2141 (0.48); 3.2048 (0.56); 3.1746 (0.57); 3.1617 (0.53); 2.6770 (2.71); 2.6725 (3.77); 2.6680 (2.92); 2.5256 (12.19); 2.5120 (206.18); 2.5079 (415.84); 2.5034 (557.11); 2.4989 (428.11); 2.4281 (1.03); 2.4196 (1.06); 2.3896 (1.81); 2.3623 (1.81); 2.3345 (3.32); 2.3301 (4.27); 2.3257 (3.44); 2.2755 (0.36); 1.9555 (2.62); 1.9237 (3.13); 1.8728 (6.33); 1.8483 (7.65); 1.8420 (7.73); 1.8104 (6.64); 1.7882 (3.76); 1.7636 (2.67); 1.7292 (0.82); 1.6867 (1.07); 1.6613 (2.24); 1.6231 (3.15); 1.5986 (4.24); 1.5920 (3.89); 1.5671 (4.01); 1.5603 (3.75); 1.5293 (2.66); 1.5033 (1.63); 1.4446 (3.08); 1.4122 (3.14); 1.3879 (3.08); 1.3632 (2.73); 1.3313 (1.97); 1.2983 (0.91); 1.2579 (0.56); 1.2486 (0.52); 1.2350 (0.88); 0.8533 (0.32); 0.1459 (1.04); 0.0079 (7.59); −0.0002 (217.92); −0.0084 (10.31); −0.1498 (0.95)

No. Ia-162, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.8583 (1.81); 8.7329 (5.95); 8.7304 (6.05); 8.3343 (6.22); 8.3303 (6.17); 8.3188 (1.03); 8.3030 (1.96); 8.2994 (1.93); 8.2562 (1.07); 8.2345 (1.11); 8.0584 (3.21); 8.0353 (3.31); 7.6113 (3.08); 7.5899 (4.20); 7.5601 (8.98); 7.5558 (3.71); 7.5437 (4.08); 7.5388 (15.31); 7.4792 (2.18); 7.4736 (15.45); 7.4688 (4.71); 7.4524 (12.47); 7.4367 (1.27); 7.4321 (3.43); 4.7086 (1.62); 4.7003 (1.81); 4.6864 (1.84); 4.6778 (1.63); 4.3863 (0.39); 4.3599 (0.39); 3.9045 (16.00); 3.6407 (1.20); 3.6325 (2.19); 3.6235 (1.42); 3.6117 (1.48); 3.6029 (2.30); 3.5946 (1.29); 3.5676 (0.37); 3.5593 (0.38); 3.5385 (0.73); 3.5309 (0.63); 3.5099 (0.43); 3.4327 (0.44); 3.4078 (0.81); 3.3462 (1127.30); 3.3027 (1.61); 3.2801 (0.85); 3.2576 (0.51); 3.2438 (0.48); 3.2143 (0.35); 3.2038 (0.33); 3.1746 (0.44); 3.1617 (0.40); 2.8913 (0.73); 2.7313 (0.60); 2.6770 (1.69); 2.6726 (2.33); 2.6681 (1.75); 2.5426 (1.67); 2.5257 (7.59); 2.5122 (130.42); 2.5080 (260.11); 2.5035 (343.43); 2.4990 (259.45); 2.4949 (134.03); 2.4160 (0.74); 2.4083 (0.81); 2.3784 (1.67); 2.3503 (1.71); 2.3398 (1.49); 2.3347 (2.04); 2.3303 (2.58); 2.3257 (2.16); 1.9568 (0.63); 1.9232 (0.85); 1.8790 (4.19); 1.8517 (5.50); 1.7997 (2.41); 1.7888 (1.78); 1.7645 (2.03); 1.7307 (0.66); 1.6826 (0.43); 1.6472 (0.62); 1.6028 (1.90); 1.5948 (1.98); 1.5588 (2.26); 1.5489 (2.03); 1.5297 (1.75); 1.5180 (1.73); 1.5077 (1.52); 1.4582 (1.63); 1.4455 (1.41); 1.4326 (1.50); 1.3632 (0.73); 1.3361 (0.64); 1.2972 (0.52); 1.2583 (0.55); 1.2491 (0.53); 1.2359 (1.07); 0.8540 (0.55); 0.8336 (0.50); 0.8119 (0.39); 0.1458 (0.63); 0.0078 (5.13); −0.0002 (135.93); −0.0084 (5.81); −0.1497 (0.61)

No. Ia-163, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.8541 (0.45); 8.7226 (2.15); 8.3320 (2.27); 8.3282 (2.26); 8.3190 (0.33); 8.2910 (0.47); 8.2873 (0.46); 7.7519 (1.22); 7.7294 (1.25); 7.5766 (0.74); 7.5541 (1.00); 7.5445 (3.60); 7.5226 (3.90); 6.9256 (3.98); 6.9037 (3.85); 6.8975 (1.31); 6.8754 (0.79); 4.6898 (0.58); 4.6819 (0.67); 4.6685 (0.70); 4.6594 (0.59); 3.9043 (4.05); 3.8240 (0.44); 3.7774 (16.00); 3.7510 (3.27); 3.6365 (0.43); 3.6286 (0.77); 3.6198 (0.52); 3.6081 (0.51); 3.5994 (0.80); 3.3443 (321.39); 2.6724 (0.66); 2.6681 (0.50); 2.5076 (78.48); 2.5033 (102.38); 2.4991 (78.45); 2.4142 (0.33); 2.3859 (0.62); 2.3568 (0.63); 2.3300 (0.90); 1.8997 (0.70); 1.8695 (1.72); 1.8401 (1.35); 1.8073 (0.65); 1.7710 (0.62); 1.7425 (0.68); 1.6001 (0.68); 1.5652 (0.66); 1.5378 (0.63); 1.5279 (0.65); 1.5039 (0.53); 1.4559 (0.54); 1.4257 (0.54); 1.4035 (0.33); 0.0079 (1.37); −0.0002 (38.31); −0.0075 (2.02)

No. Ia-164, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.9220 (2.84); 8.9193 (2.87); 8.8586 (3.86); 8.8560 (3.92); 8.4089 (2.03); 8.3782 (3.69); 8.3724 (4.25); 8.3701 (4.73); 8.3648 (4.30); 8.3174 (0.87); 8.2320 (1.68); 8.2104 (1.73); 7.5459 (2.85); 7.5436 (3.08); 7.5261 (3.56); 7.5237 (3.81); 7.5200 (2.73); 7.5174 (2.58); 7.4999 (2.66); 7.4975 (2.72); 7.3912 (1.27); 7.3887 (1.47); 7.3727 (3.30); 7.3700 (3.40); 7.3541 (2.37); 7.3513 (2.34); 7.3451 (1.26); 7.3292 (2.52); 7.3265 (2.61); 7.3080 (3.72); 7.3038 (2.64); 7.2886 (2.72); 7.2842 (2.94); 7.2753 (1.83); 7.2703 (2.77); 7.2652 (1.54); 7.2558 (2.05); 7.2513 (2.19); 7.2368 (1.01); 7.2325 (0.96); 7.0803 (2.96); 7.0760 (3.08); 7.0615 (2.77); 7.0573 (2.64); 7.0095 (2.19); 7.0051 (2.29); 6.9907 (2.05); 6.9865 (2.00); 4.7814 (1.12); 4.7653 (1.10); 4.7586 (1.09); 4.4042 (0.61); 4.3815 (0.59); 3.9040 (16.00); 3.7706 (0.39); 3.5758 (1.44); 3.5675 (0.99); 3.5537 (0.99); 3.5455 (1.52); 3.5376 (0.87); 3.4672 (0.91); 3.4601 (1.07); 3.4389 (1.58); 3.4327 (1.90); 3.4116 (2.15); 3.3535 (1518.02); 3.2301 (0.61); 3.2082 (0.48); 3.1746 (0.78); 3.1614 (0.74); 2.9991 (0.39); 2.8911 (1.68); 2.7527 (0.35); 2.7310 (1.43); 2.6770 (1.70); 2.6725 (2.34); 2.6681 (1.77); 2.5426 (1.45); 2.5257 (7.32); 2.5122 (131.26); 2.5080 (262.37); 2.5035 (346.79); 2.4990 (261.86); 2.4947 (135.18); 2.3571 (0.80); 2.3346 (2.55); 2.3302 (3.24); 2.3258 (2.69); 2.3006 (1.13); 2.2709 (0.55); 2.0326 (0.83); 2.0097 (1.14); 1.8773 (1.09); 1.8459 (2.25); 1.7961 (3.38); 1.7748 (3.83); 1.7195 (0.42); 1.5855 (1.33); 1.5555 (1.74); 1.5191 (1.89); 1.4904 (1.46); 1.4606 (2.03); 1.4331 (2.01); 1.4086 (1.39); 1.3765 (0.99); 1.3459 (0.80); 1.3358 (0.74); 1.3150 (0.64); 1.2980 (0.48); 1.2821 (0.40); 1.2582 (0.45); 1.2489 (0.49); 1.2357 (0.91); 0.8539 (0.41); 0.8346 (0.37); 0.1459 (0.56); 0.0080 (4.49); −0.0002 (127.38); −0.0084 (5.49); −0.1498 (0.55)

No. Ia-165, Solvent: <[D₆]-DMSO>, Spectrometer: 601.6 MHz

8.8748 (0.36); 8.7588 (3.03); 8.7569 (2.94); 8.3468 (3.31); 8.3441 (3.22); 8.3118 (0.37); 8.3090 (0.36); 7.9844 (1.84); 7.9694 (1.88); 7.7026 (3.83); 7.7004 (5.27); 7.6970 (6.13); 7.6938 (2.31); 7.6886 (5.52); 7.6867 (6.10); 7.6829 (8.69); 7.6799 (1.70); 7.6764 (1.76); 7.6688 (1.31); 7.6639 (0.69); 7.6382 (1.38); 7.6354 (7.88); 7.6321 (2.19); 7.6244 (1.81); 7.6213 (5.04); 7.6182 (0.68); 7.4972 (2.76); 7.4941 (1.08); 7.4848 (5.32); 7.4776 (0.59); 7.4743 (1.50); 7.4716 (3.50); 7.4686 (0.66); 7.4652 (0.66); 7.4519 (0.38); 7.4130 (1.11); 7.4111 (2.02); 7.4092 (1.12); 7.4016 (0.99); 7.3988 (2.89); 7.3960 (1.05); 7.3885 (0.67); 7.3866 (1.26); 7.3845 (0.83); 4.7343 (0.80); 4.7281 (0.90); 4.7198 (0.92); 4.7133 (0.80); 3.9026 (16.00); 3.6593 (0.62); 3.6536 (1.14); 3.6475 (0.69); 3.6402 (0.72); 3.6342 (1.16); 3.6284 (0.63); 3.3463 (0.51); 3.3376 (1.16); 3.3211 (651.14); 3.3028 (0.46); 3.2939 (0.35); 3.1726 (1.09); 3.1639 (1.07); 2.8903 (0.51); 2.7305 (0.42); 2.6191 (0.76); 2.6161 (1.61); 2.6130 (2.26); 2.6100 (1.62); 2.6069 (0.75); 2.5406 (0.54); 2.5376 (0.34); 2.5223 (4.43); 2.5192 (5.60); 2.5161 (5.54); 2.5073 (120.28); 2.5043 (260.75); 2.5012 (361.94); 2.4982 (262.79); 2.4952 (120.86); 2.4804 (0.46); 2.4773 (0.33); 2.4001 (0.69); 2.3915 (0.87); 2.3885 (1.75); 2.3854 (2.62); 2.3824 (2.25); 2.3794 (1.31); 1.9214 (0.80); 1.9145 (0.63); 1.8991 (1.61); 1.8825 (1.38); 1.8779 (1.36); 1.8626 (1.06); 1.8571 (0.91); 1.7996 (0.57); 1.7863 (0.62); 1.7801 (0.92); 1.7740 (0.57); 1.6197 (0.80); 1.6148 (0.82); 1.5976 (0.81); 1.5916 (0.77); 1.5526 (0.69); 1.5461 (0.71); 1.5380 (0.59); 1.5292 (0.60); 1.4688 (0.63); 1.4463 (0.67); 1.2370 (0.58); 0.0965 (1.10); 0.0052 (9.36); −0.0002 (304.01); −0.0057 (8.67); −0.1001 (1.09)

No. Ia-166, Solvent: <[D₆]-DMSO>, Spectrometer: 601.6 MHz

8.8723 (1.07); 8.8704 (1.04); 8.7359 (2.75); 8.7341 (2.70); 8.5624 (0.62); 8.5481 (0.64); 8.4200 (0.78); 8.4168 (1.22); 8.4136 (0.85); 8.3850 (1.49); 8.3696 (1.53); 8.3505 (2.99); 8.3477 (2.96); 8.3276 (1.30); 8.3260 (1.46); 8.3237 (1.54); 8.3222 (1.50); 8.3140 (1.37); 8.3124 (1.51); 8.3083 (2.77); 8.3039 (1.66); 8.2955 (0.59); 8.2939 (0.61); 8.2917 (0.59); 8.2901 (0.55); 8.2711 (2.37); 8.2680 (3.24); 8.2647 (2.06); 8.0373 (0.50); 8.0354 (0.70); 8.0331 (0.52); 8.0244 (0.57); 8.0221 (0.75); 8.0202 (0.54); 7.9479 (1.39); 7.9460 (1.92); 7.9437 (1.39); 7.9352 (1.59); 7.9331 (2.09); 7.9309 (1.51); 7.7162 (2.20); 7.7029 (3.69); 7.6897 (2.04); 7.6869 (1.53); 7.6737 (0.76); 4.7369 (0.71); 4.7309 (0.80); 4.7221 (0.80); 4.7161 (0.72); 3.9027 (16.00); 3.6700 (0.55); 3.6640 (1.04); 3.6580 (0.63); 3.6506 (0.65); 3.6446 (1.07); 3.6387 (0.58); 3.5663 (0.35); 3.5614 (0.33); 3.3175 (221.82); 3.1725 (1.12); 3.1638 (1.11); 2.8905 (1.15); 2.7312 (0.91); 2.6190 (0.76); 2.6159 (1.63); 2.6129 (2.29); 2.6099 (1.62); 2.6069 (0.72); 2.5405 (0.33); 2.5222 (4.25); 2.5191 (5.20); 2.5160 (5.26); 2.5072 (123.83); 2.5042 (267.21); 2.5011 (369.74); 2.4981 (271.90); 2.4951 (127.84); 2.4687 (0.36); 2.4070 (0.34); 2.3914 (1.31); 2.3883 (2.25); 2.3854 (2.79); 2.3824 (1.88); 2.3793 (0.90); 2.3693 (0.71); 2.3497 (0.32); 1.9679 (0.33); 1.9632 (0.32); 1.9079 (1.47); 1.9042 (1.00); 1.8871 (2.16); 1.8702 (1.54); 1.8508 (0.59); 1.8455 (0.62); 1.8244 (0.91); 1.8054 (0.70); 1.7995 (1.11); 1.7936 (0.76); 1.6394 (0.36); 1.6192 (0.98); 1.5974 (0.97); 1.5578 (0.70); 1.5512 (0.72); 1.5431 (0.60); 1.5347 (0.58); 1.4752 (0.68); 1.4545 (0.88); 1.4338 (0.54); 1.3815 (0.37); 1.3605 (0.32); 1.2368 (0.60); 0.0965 (1.05); 0.0053 (8.03); −0.0002 (270.63); −0.0057 (8.98); −0.0161 (0.38); −0.1000 (1.09)

No. Ia-169, Solvent: <[D₆]-DMSO>, Spectrometer: 601.6 MHz

8.9767 (0.56); 8.9635 (0.56); 8.9111 (0.84); 8.9093 (0.80); 8.8782 (2.83); 8.4619 (0.89); 8.4591 (0.87); 8.4062 (2.45); 7.6285 (0.72); 7.6269 (0.74); 7.6152 (0.92); 7.6135 (0.95); 7.6089 (2.72); 7.6076 (2.83); 7.5958 (3.00); 7.5942 (2.98); 7.4431 (0.40); 7.4413 (0.40); 7.4338 (1.30); 7.4320 (1.48); 7.4289 (0.96); 7.4214 (3.11); 7.4196 (3.08); 7.4166 (0.77); 7.4090 (2.10); 7.4072 (1.98); 7.3675 (0.51); 7.3645 (0.61); 7.3546 (0.72); 7.3501 (1.74); 7.3472 (2.04); 7.3417 (0.61); 7.3374 (2.12); 7.3343 (2.82); 7.3246 (3.94); 7.3217 (3.40); 7.3170 (1.00); 7.3124 (2.40); 7.3096 (1.88); 7.3046 (0.65); 5.1644 (0.47); 5.1543 (0.47); 4.9767 (0.32); 3.9026 (16.00); 3.6657 (7.14); 3.5971 (0.34); 3.5868 (1.32); 3.5774 (1.13); 3.5715 (0.52); 3.5619 (1.62); 3.5528 (1.24); 3.4486 (0.47); 3.4347 (0.48); 3.4227 (0.41); 3.4090 (0.45); 3.3878 (0.44); 3.3182 (78.27); 3.1713 (1.87); 3.1645 (1.79); 2.6186 (1.19); 2.6157 (2.18); 2.6126 (2.88); 2.6096 (2.11); 2.6065 (1.11); 2.5402 (2.27); 2.5219 (9.18); 2.5188 (11.21); 2.5157 (12.58); 2.5069 (157.14); 2.5039 (318.96); 2.5009 (429.75); 2.4978 (309.68); 2.4948 (140.64); 2.4738 (0.49); 2.3911 (0.92); 2.3881 (1.89); 2.3851 (2.55); 2.3820 (1.80); 2.3790 (0.80); 1.9077 (1.13); 0.0965 (0.90); 0.0197 (0.52); 0.0052 (9.06); −0.0002 (226.43); −0.0058 (7.18); −0.1001 (0.86)

No. Ia-170, Solvent: <CD₃CN>, Spectrometer: 601.6 MHz

8.7668 (3.74); 8.7654 (4.02); 8.1011 (3.83); 8.0988 (4.21); 7.4459 (0.72); 7.4350 (1.47); 7.4317 (1.62); 7.4241 (0.89); 7.4209 (2.95); 7.4178 (1.36); 7.4100 (1.43); 7.4068 (1.78); 7.3960 (0.74); 7.0524 (0.87); 7.0434 (0.92); 7.0386 (0.87); 7.0101 (0.61); 7.0080 (0.88); 7.0032 (4.53); 6.9958 (0.77); 6.9938 (1.10); 6.9899 (5.73); 6.9893 (6.18); 6.9762 (4.22); 6.9716 (0.84); 6.9696 (0.63); 4.7280 (0.62); 4.7168 (1.11); 4.7154 (1.15); 4.7139 (1.12); 4.7042 (1.41); 4.7027 (1.60); 4.6930 (0.91); 4.6915 (1.17); 4.6901 (1.32); 4.6790 (0.70); 3.2613 (0.50); 3.2486 (0.43); 3.2377 (3.27); 3.2297 (3.42); 3.2253 (3.85); 3.2191 (3.37); 3.2062 (0.53); 3.1954 (0.40); 2.1626 (62.51); 1.9668 (0.83); 1.9587 (0.70); 1.9545 (1.19); 1.9508 (12.12); 1.9467 (23.29); 1.9425 (35.28); 1.9385 (25.62); 1.9344 (13.22); 1.4358 (2.83); 1.3009 (0.36); 1.2853 (15.91); 1.2741 (16.00); 0.0053 (0.38); −0.0002 (10.70)

No. Ia-171, Solvent: <CD₃CN>, Spectrometer: 601.6 MHz

8.7612 (3.44); 8.7597 (3.43); 8.0992 (3.58); 8.0967 (3.55); 7.0668 (0.73); 7.0554 (0.74); 6.8801 (0.40); 6.8735 (1.27); 6.8711 (3.55); 6.8648 (0.57); 6.8584 (4.75); 6.8558 (4.83); 6.8494 (0.54); 6.8431 (3.52); 6.8406 (1.27); 6.8342 (0.36); 4.7084 (0.68); 4.6970 (1.34); 4.6943 (0.90); 4.6852 (1.45); 4.6828 (1.49); 4.6738 (0.89); 4.6712 (1.33); 4.6597 (0.69); 3.2282 (5.69); 3.2165 (6.69); 2.3799 (0.44); 2.1624 (73.49); 1.9670 (2.60); 1.9589 (1.66); 1.9546 (2.27); 1.9509 (16.54); 1.9468 (29.63); 1.9427 (42.17); 1.9385 (29.54); 1.9344 (15.17); 1.4362 (0.94); 1.2963 (0.32); 1.2823 (15.88); 1.2712 (16.00); −0.0002 (7.00)

No. Ia-172, Solvent: <CD₃CN>, Spectrometer: 601.6 MHz

8.7526 (4.03); 8.7512 (4.01); 8.0886 (4.13); 8.0863 (4.09); 7.7081 (1.42); 7.7050 (1.51); 7.6953 (2.88); 7.6923 (2.99); 7.6825 (1.52); 7.6795 (1.53); 7.5110 (0.76); 7.5079 (0.78); 7.5023 (0.86); 7.4989 (1.67); 7.4972 (1.38); 7.4957 (1.32); 7.4943 (1.14); 7.4899 (1.18); 7.4884 (1.31); 7.4868 (1.42); 7.4852 (1.74); 7.4819 (0.96); 7.4762 (0.91); 7.4732 (0.85); 7.2537 (2.11); 7.2522 (2.22); 7.2411 (3.58); 7.2397 (3.75); 7.2286 (1.83); 7.2271 (1.89); 7.1811 (2.51); 7.1797 (2.53); 7.1673 (2.50); 7.1659 (2.47); 7.1621 (2.54); 7.1607 (2.45); 7.1483 (1.88); 7.1469 (1.82); 4.7179 (0.47); 4.7161 (0.55); 4.7048 (1.29); 4.6934 (1.69); 4.6821 (1.29); 4.6707 (0.55); 4.6690 (0.49); 3.2755 (5.47); 3.2642 (6.91); 2.3808 (0.54); 2.1904 (21.04); 1.9698 (0.38); 1.9574 (0.47); 1.9537 (2.99); 1.9496 (5.35); 1.9455 (7.70); 1.9414 (5.29); 1.9373 (2.69); 1.4327 (1.74); 1.3035 (15.97); 1.2923 (16.00); −0.0002 (1.55)

No. Ia-173, Solvent: <CD₃CN>, Spectrometer: 601.6 MHz

8.7812 (3.35); 8.7796 (3.32); 8.1041 (3.51); 8.1014 (3.46); 7.3701 (0.41); 7.3658 (3.78); 7.3625 (4.77); 7.3505 (10.61); 7.3285 (6.10); 7.3176 (2.86); 7.3131 (2.07); 7.3021 (1.78); 6.9434 (0.72); 6.9310 (0.72); 4.7837 (0.57); 4.7805 (0.33); 4.7729 (0.88); 4.7695 (1.12); 4.7662 (0.34); 4.7621 (0.76); 4.7586 (1.61); 4.7551 (0.74); 4.7510 (0.34); 4.7478 (1.15); 4.7443 (0.87); 4.7368 (0.34); 4.7336 (0.58); 3.3260 (1.57); 3.3120 (1.55); 3.3022 (2.32); 3.2882 (2.29); 3.2063 (1.95); 3.1961 (1.96); 3.1824 (1.34); 3.1723 (1.29); 2.1576 (119.10); 2.0528 (0.40); 1.9665 (1.61); 1.9584 (1.44); 1.9541 (2.37); 1.9504 (25.69); 1.9463 (48.19); 1.9422 (68.94); 1.9381 (47.97); 1.9340 (24.54); 1.9253 (0.44); 1.8275 (0.39); 1.4363 (0.47); 1.3133 (15.99); 1.3022 (16.00); 0.0052 (0.95); −0.0002 (26.47); −0.0058 (0.87)

No. Ia-174, Solvent: <CD₃CN>, Spectrometer: 601.6 MHz

8.7742 (3.29); 8.7725 (3.22); 8.1109 (3.41); 8.1083 (3.35); 7.6015 (0.57); 7.6002 (0.55); 7.5923 (0.69); 7.5909 (0.78); 7.5877 (1.37); 7.5871 (1.37); 7.5788 (1.37); 7.5779 (1.41); 7.5745 (1.13); 7.5732 (1.05); 7.5654 (1.06); 7.5643 (1.02); 7.5406 (3.50); 7.5275 (1.96); 7.4252 (1.47); 7.4106 (2.52); 7.3965 (1.20); 7.0567 (0.70); 7.0444 (0.70); 4.7588 (0.63); 4.7478 (1.09); 4.7458 (0.98); 4.7365 (0.92); 4.7346 (1.41); 4.7318 (0.85); 4.7226 (1.01); 4.7206 (1.05); 4.7095 (0.64); 3.3021 (1.45); 3.2892 (1.43); 3.2782 (2.23); 3.2653 (2.18); 3.1896 (1.98); 3.1788 (1.98); 3.1657 (1.32); 3.1549 (1.29); 2.3799 (0.47); 2.1618 (46.74); 1.9668 (0.93); 1.9587 (0.78); 1.9544 (1.27); 1.9507 (15.41); 1.9466 (28.43); 1.9425 (41.41); 1.9384 (29.18); 1.9343 (14.76); 1.9296 (0.51); 1.4361 (0.64); 1.2668 (16.00); 1.2556 (15.90); 0.0053 (0.50); −0.0002 (15.34); −0.0058 (0.45)

No. Ia-175, Solvent: <CD₃CN>, Spectrometer: 601.6 MHz

8.7747 (3.18); 8.7730 (3.19); 8.0989 (3.26); 8.0963 (3.27); 7.4582 (0.88); 7.4548 (1.00); 7.4464 (1.94); 7.4431 (2.47); 7.4348 (2.26); 7.4312 (4.21); 7.4225 (4.59); 7.4198 (2.66); 7.4159 (3.19); 7.4134 (3.92); 7.4044 (1.93); 7.4023 (1.84); 7.4009 (1.34); 7.3917 (0.77); 7.3893 (0.89); 7.3843 (2.45); 7.3719 (1.71); 6.9376 (0.75); 6.9243 (0.75); 4.7032 (0.66); 4.6918 (1.22); 4.6888 (0.81); 4.6800 (1.38); 4.6775 (1.32); 4.6688 (0.85); 4.6657 (1.26); 4.6544 (0.69); 3.8577 (0.37); 3.8388 (1.19); 3.8331 (0.59); 3.8199 (1.29); 3.8142 (1.66); 3.8010 (0.51); 3.7953 (1.66); 3.7764 (0.55); 3.7144 (0.50); 3.6955 (1.60); 3.6899 (0.48); 3.6766 (1.70); 3.6709 (1.22); 3.6576 (0.63); 3.6520 (1.18); 3.6330 (0.39); 3.2491 (6.82); 3.2374 (5.79); 2.3799 (0.46); 2.1823 (0.42); 2.1750 (0.37); 2.1572 (186.69); 2.0568 (0.51); 2.0526 (0.76); 2.0485 (0.54); 1.9738 (0.38); 1.9664 (17.99); 1.9582 (3.41); 1.9541 (4.80); 1.9503 (48.40); 1.9462 (92.40); 1.9421 (138.36); 1.9380 (95.38); 1.9339 (47.38); 1.9196 (0.38); 1.8315 (0.52); 1.8273 (0.75); 1.8232 (0.54); 1.4365 (0.37); 1.2918 (15.91); 1.2806 (16.00); 1.2693 (0.38); 0.0053 (1.20); −0.0002 (36.79); −0.0058 (1.45)

No. Ia-176, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.8966 (5.59); 8.8938 (5.51); 8.5417 (3.13); 8.5206 (3.20); 8.4215 (5.74); 8.4174 (5.77); 7.6428 (9.29); 7.6378 (9.91); 7.4898 (4.58); 7.4847 (4.25); 7.4693 (6.24); 7.4642 (6.09); 7.3673 (10.56); 7.3468 (7.77); 4.6262 (0.66); 4.6071 (1.47); 4.5904 (1.96); 4.5731 (1.35); 4.5536 (0.68); 3.3354 (237.36); 3.3119 (1.60); 3.2342 (0.90); 3.2179 (0.99); 3.1991 (3.34); 3.1823 (3.73); 3.1785 (4.03); 3.1585 (3.24); 3.1435 (1.00); 3.1238 (1.01); 2.6719 (0.41); 2.5255 (0.69); 2.5208 (1.04); 2.5115 (23.17); 2.5074 (44.64); 2.5032 (61.62); 2.4990 (42.97); 2.4949 (21.41); 2.3298 (0.37); 1.2257 (16.00); 1.2089 (15.91); −0.0002 (5.08)

No. Ia-177, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8,9455 (2,86); 8,4485 (0,81); 8,4342 (1,51); 8,4115 (3,07); 8,407 (2,97); 7,8472 (2,44); 7,8278 (2,54); 7,4273 (1,1); 7,4086 (2,46); 7,3899 (1,48); 7,2365 (2); 7,2327 (2,33); 7,2176 (1,78); 7,2138 (1,84); 7,1552 (1,23); 7,1512 (1,17); 7,1361 (1,99); 7,1323 (1,94); 7,117 (1,04); 7,1129 (0,95); 3,8587 (0,62); 3,8416 (1,33); 3,8244 (1,42); 3,8073 (0,77); 3,6417 (0,68); 3,626 (0,86); 3,6096 (1,33); 3,5935 (1,66); 3,5774 (0,81); 3,5514 (0,9); 3,5377 (1,1); 3,5334 (0,99); 3,5193 (1,3); 3,5053 (0,54); 3,5008 (0,53); 3,4871 (0,43); 3,3215 (13,79); 2,5063 (29,88); 2,5019 (40,17); 2,4977 (31,28); 1,3977 (16); 1,2884 (8,04); 1,2712 (8,13); 1,25 (0,36); −0,0002 (4,31)

No. Ia-178, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8,9756 (5,13); 8,9728 (5,03); 8,926 (0,68); 8,9231 (0,67); 8,421 (5,24); 8,42 (5,34); 8,4161 (5,35); 8,4063 (0,81); 8,4011 (0,75); 8,3389 (3,04); 8,3154 (3,1); 8,1383 (0,39); 8,1158 (0,4); 7,8914 (4,34); 7,8892 (4,55); 7,8717 (4,72); 7,8694 (4,62); 7,8367 (0,58); 7,8345 (0,61); 7,8148 (0,89); 7,4926 (2,08); 7,49 (2,04); 7,4739 (4,73); 7,4712 (4,55); 7,4551 (2,92); 7,4525 (2,79); 7,4095 (0,56); 7,3907 (0,77); 7,3881 (0,65); 7,3719 (0,43); 7,3693 (0,41); 7,3283 (4,08); 7,3243 (4,56); 7,3094 (3,53); 7,3054 (3,46); 7,1932 (2,56); 7,189 (2,51); 7,1741 (3,84); 7,17 (3,66); 7,1548 (2,23); 7,1507 (2,06); 7,1442 (0,41); 7,1401 (0,4); 7,1251 (0,51); 7,1209 (0,56); 7,0261 (0,64); 7,0224 (0,74); 7,0073 (0,57); 7,0034 (0,56); 5,7579 (7,98); 5,4406 (0,56); 4,4159 (1,06); 4,4037 (1,28); 4,3915 (1,41); 4,3816 (1,52); 4,3698 (1,46); 4,36 (1,55); 4,3469 (0,67); 4,337 (0,64); 3,7614 (0,44); 3,6957 (0,51); 3,6787 (2,04); 3,6613 (2,4); 3,6585 (2,31); 3,641 (1,99); 3,624 (0,5); 3,3297 (15,94); 2,5281 (0,43); 2,5232 (0,68); 2,5148 (8,4); 2,5103 (16,86); 2,5058 (22,24); 2,5012 (16,14); 2,4967 (7,78); 1,4116 (0,54); 1,3933 (0,82); 1,3886 (0,6); 1,3771 (1,42); 1,358 (1,86); 1,3546 (1,84); 1,3381 (3,73); 1,3279 (1,86); 1,3113 (16); 1,2942 (15,41); 1,2709 (2,34); 1,2599 (0,96); 1,2505 (2,24); 1,2345 (0,46); 0,9763 (0,94); 0,9581 (1,98); 0,9396 (0,9); 0,9187 (6,94); 0,9005 (14,55); 0,882 (5,81); 0,0079 (0,54); −0,0002 (15,36); −0,0085 (0,52)

No. Ia-196, Solvent: <CD₃CN>, Spectrometer: 399.95 MHz

8,786 (4,01); 8,1069 (4,22); 8,103 (4,26); 7,9518 (2,96); 7,9507 (3,07); 7,9326 (3,25); 7,9305 (3,41); 7,7274 (1,41); 7,7249 (1,52); 7,7086 (3,43); 7,7061 (3,51); 7,6898 (2,33); 7,6872 (2,27); 7,6288 (2,08); 7,6254 (2,3); 7,6093 (2,86); 7,6077 (2,82); 7,6059 (3,15); 7,5897 (1,43); 7,5863 (1,36); 7,4708 (3,43); 7,4676 (3,53); 7,452 (2,98); 7,4487 (3,04); 7,0951 (0,92); 7,0824 (0,9); 4,6789 (0,67); 4,6619 (1,28); 4,6414 (1,59); 4,6232 (1,33); 4,6058 (0,72); 3,3012 (0,7); 3,2824 (0,55); 3,266 (3,62); 3,2478 (4,63); 3,2358 (3,7); 3,2164 (0,73); 3,2005 (0,58); 2,3794 (0,7); 2,2514 (1,45); 2,075 (0,58); 1,9652 (0,39); 1,9532 (4,68); 1,9471 (8,95); 1,941 (12,67); 1,9348 (9,06); 1,9287 (4,89); 1,2996 (15,95); 1,2828 (16); 1,1849 (0,7); 1,174 (0,55); 1,1689 (0,68); −0,0002 (0,36)

No. Ia-197, Solvent: <CDCl₃>, Spectrometer: 400 MHz

See FIG. 1

No. Ia-198, Solvent: <CDCl₃>, Spectrometer: 400 MHz

See FIG. 2

No. Ia-199, Solvent: <CDCl₃>, Spectrometer: 400 MHz

See FIG. 3

No. Ia-200, Solvent: <CDCl₃>, Spectrometer: 400 MHz

See FIG. 4

No. Ia-201, Solvent: <CDCl₃>, Spectrometer: 400 MHz

See FIG. 5

No. Ia-202, Solvent: <CDCl₃>, Spectrometer: 400 MHz

See FIG. 6

No. Ia-203, Solvent: <CDCl₃>, Spectrometer: 400 MHz

See FIG. 7

No. Ia-204, Solvent: <CDCl₃>, Spectrometer: 400 MHz

See FIG. 8

No. Ia-205, Solvent: <CDCl₃>, Spectrometer: 400 MHz

See FIG. 9

No. Ia-206, Solvent: <CDCl₃>, Spectrometer: 400 MHz

See FIG. 10

No. Ia-207, Solvent: <CDCl₃>, Spectrometer: 400 MHz

See FIG. 11

No. Ia-208, Solvent: <CDCl₃>, Spectrometer: 400 MHz

See FIG. 12

No. Ia-209, Solvent: <CDCl₃>, Spectrometer: 400 MHz

See FIG. 13

No. Ia-210, Solvent: <CDCl₃>, Spectrometer: 400 MHz

See FIG. 14

No. Ia-211, Solvent: <CDCl₃>, Spectrometer: 400 MHz

See FIG. 15

No. Ia-212, Solvent: <CDCl₃>, Spectrometer: 400 MHz

See FIG. 16

No. Ia-213, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8,6943 (8,93); 8,6888 (9,05); 8,6009 (1,67); 8,5867 (3,15); 8,5731 (1,64); 8,2203 (10); 8,2149 (9,72); 7,8099 (0,45); 7,7973 (0,88); 7,7781 (1,1); 7,7536 (0,77); 7,7284 (4,43); 7,7186 (1,69); 7,7084 (5,04); 7,6823 (1,99); 7,6649 (4,35); 7,6464 (3,2); 7,616 (3,13); 7,5969 (3,64); 7,5782 (1,32); 7,4598 (0,35); 7,4046 (1); 7,3985 (8,03); 7,3937 (3,04); 7,3823 (3,96); 7,3772 (16); 7,3715 (2,34); 7,3364 (2,39); 7,3306 (14,49); 7,3256 (3,91); 7,3141 (2,91); 7,3092 (7,85); 7,2958 (0,38); 7,2736 (4,1); 7,2551 (3,75); 4,9169 (2,2); 4,8984 (4,83); 4,8795 (2,36); 4,0561 (0,58); 4,0383 (1,73); 4,0205 (1,76); 4,0027 (0,6); 3,9703 (0,43); 3,9572 (0,56); 3,9507 (0,49); 3,9376 (2,62); 3,9251 (3,85); 3,9181 (2,73); 3,908 (4,02); 3,8922 (2,42); 3,8766 (0,67); 3,8595 (0,42); 3,3261 (17,26); 3,2703 (0,43); 3,2514 (0,34); 2,9988 (0,41); 2,6761 (0,54); 2,6715 (0,73); 2,667 (0,53); 2,5247 (2,33); 2,5114 (41,27); 2,507 (82,25); 2,5024 (109,07); 2,4978 (79,67); 2,4933 (38,17); 2,3337 (0,54); 2,3292 (0,74); 2,3246 (0,53); 1,9894 (7,57); 1,9097 (0,36); 1,2582 (0,41); 1,2347 (2,64); 1,1929 (2,21); 1,1752 (4,25); 1,1666 (0,44); 1,1573 (2,14); 1,1483 (0,64); 1,1383 (0,88); 1,1299 (0,35); 1,1207 (1,65); 1,103 (0,79); 1,0907 (0,34); 0,9999 (0,82); 0,9822 (1,67); 0,9644 (0,77); 0,8533 (0,36); 0,0127 (0,97); 0,008 (1,58); −0,0002 (41,92); −0,0085 (1,25)

No. Ia-214, Solvent: <CD₃CN>, Spectrometer: 399.95 MHz

8,4875 (4,24); 8,482 (4,18); 7,9367 (2,27); 7,9342 (2,26); 7,9164 (2,61); 7,9139 (2,58); 7,8839 (4,89); 7,8785 (4,73); 7,7042 (1,16); 7,7012 (1,22); 7,6854 (2,98); 7,6824 (2,95); 7,6666 (2,11); 7,6635 (1,96); 7,6175 (1,82); 7,6138 (1,98); 7,5973 (2,27); 7,5938 (2,28); 7,5784 (1,13); 7,5747 (1,08); 7,4476 (2,8); 7,4442 (2,7); 7,4287 (2,35); 7,4254 (2,29); 7,0253 (0,67); 3,7929 (0,73); 3,7759 (1,23); 3,7737 (1,16); 3,7588 (1,48); 3,7418 (1,14); 3,7249 (0,36); 3,7042 (0,45); 3,6888 (0,57); 3,6713 (2,64); 3,6605 (3,07); 3,6558 (3,58); 3,6458 (2,92); 3,6409 (3,72); 3,6261 (2,05); 3,6128 (0,43); 3,6078 (0,39); 3,593 (0,34); 2,1486 (7,16); 1,9646 (1,08); 1,9586 (1,68); 1,9526 (7,29); 1,9465 (12,8); 1,9404 (16,77); 1,9342 (11,52); 1,928 (5,9); 1,3719 (1,32); 1,2751 (16); 1,258 (14,71); −0,0002 (5,3)

No. Ia-215, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8,9706 (5,11); 8,9678 (4,99); 8,6618 (3,04); 8,6383 (3,13); 8,4281 (5,48); 8,4241 (5,31); 8,029 (4,06); 8,0264 (4,31); 8,0087 (4,72); 8,0061 (4,7); 7,8357 (1,84); 7,8328 (1,9); 7,8168 (4,61); 7,814 (4,53); 7,798 (3,08); 7,7951 (2,91); 7,7164 (2,76); 7,7129 (3,18); 7,6966 (3,55); 7,6933 (3,81); 7,6773 (1,94); 7,6738 (1,94); 7,6084 (4,41); 7,6051 (4,33); 7,5896 (3,89); 7,5862 (3,56); 5,7574 (6,85); 4,3974 (0,53); 4,3871 (0,66); 4,3746 (1,41); 4,3645 (1,53); 4,3529 (1,46); 4,3429 (1,55); 4,3303 (0,61); 4,3201 (0,57); 3,7051 (0,52); 3,6881 (2,04); 3,6707 (2,39); 3,668 (2,31); 3,6505 (1,99); 3,6334 (0,5); 3,326 (27,53); 2,5266 (0,81); 2,5218 (1,29); 2,5133 (16,19); 2,5088 (32,58); 2,5043 (43,11); 2,4997 (31,19); 2,4951 (14,91); 1,4144 (0,55); 1,3971 (1,75); 1,3799 (1,46); 1,3612 (1,92); 1,3572 (1,87); 1,3374 (6,02); 1,3247 (1,82); 1,3143 (1,91); 1,3081 (1,41); 1,2939 (16); 1,2769 (15,49); 1,2664 (1,44); 1,2594 (2,06); 1,2501 (5,13); 1,2355 (0,93); 1,1889 (0,47); 1,1713 (0,46); 1,1543 (0,33); 0,9491 (0,33); 0,9309 (0,65); 0,9124 (0,35); 0,8904 (7,07); 0,8721 (15,21); 0,8537 (6,13); 0,0079 (1,02); −0,0002 (28,13); −0,0086 (0,94)

No. Ia-216, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8,9643 (4,8); 8,9615 (4,68); 8,8829 (0,53); 8,8801 (0,52); 8,6458 (2,66); 8,622 (2,69); 8,4325 (4,78); 8,431 (5,11); 8,4273 (4,96); 8,4261 (4,8); 8,4128 (0,32); 8,3664 (0,57); 8,3627 (0,55); 7,7485 (0,53); 7,7269 (0,53); 7,7053 (0,5); 7,5536 (0,84); 7,5369 (1,78); 7,5323 (1,52); 7,5202 (1,21); 7,5158 (3,18); 7,5115 (1,2); 7,499 (1,56); 7,4947 (1,93); 7,478 (0,85); 7,4304 (0,37); 7,3462 (0,73); 7,3247 (1,35); 7,318 (0,34); 7,3154 (0,48); 7,3127 (0,82); 7,3035 (0,66); 7,2909 (1,39); 7,2693 (0,77); 7,2665 (0,46); 7,2164 (1,2); 7,2065 (0,69); 7,2033 (0,91); 7,1957 (5,58); 7,1768 (6,54); 7,175 (6,19); 7,156 (4,57); 7,1481 (0,78); 7,0912 (0,63); 7,0725 (0,74); 7,0705 (0,69); 7,0517 (0,53); 5,7584 (12,48); 4,4502 (0,5); 4,44 (0,63); 4,427 (1,47); 4,4169 (1,67); 4,4039 (1,51); 4,3937 (1,61); 4,3807 (0,57); 4,3703 (0,56); 3,6379 (0,5); 3,6208 (1,89); 3,6037 (2,07); 3,5984 (1,95); 3,5813 (1,83); 3,5643 (0,49); 3,3287 (16,59); 2,5285 (0,62); 2,5238 (0,99); 2,5152 (11,55); 2,5106 (23,37); 2,506 (30,99); 2,5014 (22,41); 2,4969 (10,69); 1,338 (1,67); 1,3318 (0,57); 1,3131 (0,71); 1,3079 (0,51); 1,297 (1,53); 1,2895 (1,08); 1,2779 (2,31); 1,2634 (16); 1,2505 (7,89); 1,2463 (15,64); 1,2248 (0,92); 1,2181 (0,67); 1,2073 (0,4); 1,1486 (0,34); 0,9363 (0,72); 0,9181 (1,57); 0,8997 (0,68); 0,8502 (6,65); 0,8321 (14,24); 0,8136 (5,57); 0,008 (0,83); −0,0002 (23,6); −0,0085 (0,75)

TABLE B

Compounds of formula (Ib)

(Ib)

embedded image

No.
X_n
R¹
R²
R³
R⁴
R⁵
R_m
cf.

Ib-1
5-Cl
H
H
COOMe
H
H
H
P7

6-OMe

Ib-2
5-Cl
H
H
COOMe
H
H
4-OMe
P7

6-OMe

Ib-3
5-Cl
H
H
COOMe
H
H
4-Cl
P7

6-OMe

Ib-4
5-Cl
H
H
COOMe
H
H
3-CF₃
P7

6-OMe

Ib-5
5-Cl
H
H
COOMe
H
H
2-Cl
P7

6-OMe

Ib-6
5-Cl
H
H
COOMe
H
H
4-C₆H₅

6-OMe

Ib-7
5-Cl
H
H
COOMe
H
H
2-Br
P7

6-OMe

Ib-8
5-Cl
H
H
CONHEt
H
H
H
P7

6-OMe

Ib-9
5-Cl
H
H
CONHEt
H
H
4-OMe
P7

6-OMe

Ib-10
5-Cl
H
H
CONHEt
H
H
2-Cl
P7

6-OMe

Ib-11
5-Cl
H
H
CONHEt
H
H
4-C₆H₅

6-OMe

Ib-12
5-Cl
H
H
CONHEt
H
H
4-Cl
P7

6-OMe

NMR

Ib-13
5-Cl
H
H
CONHEt
H
H
3-NO₂
P7

6-OMe

NMR

Ib-14
5-Cl
H
H
CONHEt
H
H
3-CF₃
P7

6-OMe

NMR

Ib-15
5-Cl
H
H
CONHEt
H
H
2-Br
P7

6-OMe

Ib-16
5-Cl
H
H
CONHMe
H
H
4-OMe
P7

6-OMe

NMR

Ib-17
5-Cl
H
H
CONHMe
H
H
4-Cl
P7

6-OMe

NMR

Ib-18
5-Cl
H
H
COOMe
H
H
3-NO₂
P7

6-OMe

(M + 1) = 394

Ib-19
5-Cl
H
H
CONHMe
H
H
H
P7

6-OMe

NMR

Ib-20
5-Cl
H
H
CONHMe
H
H
3-NO₂
P7

6-OMe

(M + 1) = 393

Ib-21
5-Cl
H
H
CONHMe
H
H
3-CF₃
P7

6-OMe

NMR

Ib-22
5-Cl
H
H
CONHMe
H
H
2-Cl
P7

6-OMe

6-Cl
NMR

Ib-23
5-Cl
H
H
CONHMe
H
H
4-C₆H₅
P7

6-OMe

NMR

Ib-24
5-Cl
H
H
CONHMe
H
H
2-Br
P7

6-OMe

NMR

Ib-25
5-Cl
H
H
COOEt
H
H
H
P7

6-OMe

NMR

Ib-26
5-Cl
H
H
COOEt
H
H
4-OMe
P7

6-OMe

NMR

Ib-27
5-Cl
H
H
COOEt
H
H
4-Cl
P7

6-OMe

Ib-28
5-Cl
H
H
COOEt
H
H
3-CF₃
P7

6-OMe

NMR

Ib-29
5-Cl
H
H
COOEt
H
H
2-Cl
P7

6-OMe

6-Cl
NMR

Ib-30
5-Cl
H
H
COOEt
H
H
2-Br
P7

6-OMe

NMR

Ib-31
5-Cl
H
H
COOEt
H
H
3-NO₂
P7

6-OMe

Ib-32
5-Cl
H
H
COOEt
H
H
4-C₆H₅
NMR

6-OMe

Ib-33
6-CF₃
H
H
H
H
H
2-Cl
P7

cpd. 1

Ib-34
6-CF₃
H
H
H
H
H
2-Me
P7

cpd. 2

Ib-35
6-CF₃
H
H
H
H
H
2-Br
P7

cpd. 3

Ib-36
6-CF₃
H
H
H
H
H
2-CF₃
P7

cpd. 4

Ib-37
6-Cl
H
H
H
H
H
2-Cl
P7

cpd. 5

Ib-38
6-Cl
H
H
H
H
H
2-CF₃
P7

cpd. 6

Ib-39
6-Cl
CH₃
H
H
H
H
2-Cl
P7

cpd. 7

Ib-40
6-Cl
CH₃
H
H
H
H
2-Me
P7

cpd. 8

Ib-41
6-Cl
CH₃
H
H
H
H
2-Br
P7

cpd. 9

Ib-42
6-Cl
CH₃
H
H
H
H
2-I
P7

cpd. 10

Ib-43
6-Cl
CH₃
H
H
H
H
2-CF₃
P7

cpd. 11

Ib-44
6-Cl
H
H
H
H
H
2-I
P7

cpd. 12

Ib-45
2-Cl
H
H
H
H
H
2-CF₃
P7

4-Cl

cpd. 13

Ib-46
6-CH₂CH₂CF₃
H
H
H
H
H
2-CF₃
P7

Ib-47
4-Cl
H
H
H
H
H
2-CF₃
P7

6-CF₃

NMR

Ib-48
4-Cl
H
H
H
H
H
2-F
P7

6-CF₃

NMR

Ib-49
4-Cl
H
H
H
H
H
2-Cl
P7

6-CF₃

NMR

Ib-50
4-Cl
H
H
H
H
H
2-CHF₂
P7

6-CF₃

NMR

Ib-51
4-Cl
H
H
H
H
H
2-F
P7

6-CF₃

6-F
NMR

Ib-52
4-Cl
H
H
H
H
H
2-Br
P7

6-CF₃

NMR

Ib-53⁴
4-Cl
H
H
H
H
H
2-CF₃
P7

6-CF₃

NMR

Ib-54⁴
4-Cl
H
H
H
H
H
2-Cl
P7

6-CF₃

NMR

Ib-55⁴
6-Cl
H
H
H
H
H
2-CF₃
P7

NMR

Ib-56⁴
6-Cl
H
H
H
H
H
2-Cl
P7

NMR

Ib-57
4-Cl
H
H
H
H
H
2-I
P7

6-CF₃

NMR

Ib-58
4-Cl
H
H
H
H
H
2-NO₂
P7

6-CF₃

NMR

Ib-59
2-Cl
H
H
H
H
H
2-F
P7

6-CF₃

NMR

Ib-60
2-Cl
H
H
H
H
H
2-Br
P7

6-CF₃

NMR

Ib-61
2-Cl
H
H
H
H
H
2-I
P7

6-CF₃

NMR

Ib-62
2-Cl
H
H
H
H
H
2-Cl
P7

6-CF₃

NMR

Ib-63
2-Cl
H
H
H
H
H
2-CF₃
P7

6-CF₃

NMR

Ib-64
2-Cl
H
H
H
H
H
2-F
P7

6-CF₃

6-F
NMR

Ib-65
6-Cl
H
H
H
H
H
2-F
P7

NMR

Ib-66
6-Cl
H
H
H
H
H
2-F
P7

6-F
NMR

Ib-67
6-Cl
F
F
H
H
H
2-F
P7

NMR

Ib-68
6-Cl
F
F
H
H
H
2-Cl
P7

NMR

Ib-69
6-Cl
F
F
H
H
H
2-Br
P7

NMR

Ib-70
6-Cl
F
F
H
H
H
2-I
P7

NMR

Ib-71
6-Cl
F
F
H
H
H
2-F
P7

6-F
NMR

Ib-72
6-Cl
F
F
H
H
H
2-CF₃
P7

NMR

¹cis-isomer,

²trans-isomer,

³pure enantiomer, absolute configuration not determined,

⁴pyridine-N-oxide

No. Ib-12, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.7081 (1.30); 8.6868 (1.31); 8.1108 (0.66); 8.0971 (1.28); 8.0834 (0.66); 8.0247 (2.59); 8.0197 (2.72); 7.8521 (3.87); 7.8474 (1.47); 7.8309 (6.58); 7.8274 (3.63); 7.5532 (4.52); 7.5486 (1.47); 7.5363 (1.29); 7.5316 (3.92); 4.6267 (0.40); 4.6147 (0.47); 4.6017 (0.70); 4.5929 (0.63); 4.5800 (0.52); 4.5683 (0.42); 3.9157 (0.79); 3.9048 (2.55); 3.8670 (16.00); 3.4210 (0.47); 3.4047 (0.73); 3.3512 (429.39); 3.2870 (0.35); 3.1741 (0.47); 3.1615 (0.46); 3.1386 (0.41); 3.1202 (1.09); 3.1024 (1.53); 3.0883 (1.53); 3.0706 (1.12); 3.0525 (0.51); 3.0450 (0.63); 3.0329 (0.73); 3.0105 (1.02); 2.9990 (0.94); 2.9441 (0.99); 2.9185 (0.98); 2.9102 (0.67); 2.8842 (0.57); 2.6770 (0.54); 2.6726 (0.75); 2.6682 (0.56); 2.5427 (0.40); 2.5258 (2.39); 2.5123 (43.73); 2.5080 (87.18); 2.5035 (115.46); 2.4989 (87.25); 2.4946 (44.61); 2.3347 (0.56); 2.3302 (0.76); 2.3257 (0.57); 1.0197 (3.85); 1.0016 (8.14); 0.9836 (3.69); 0.0080 (1.58); −0.0002 (48.07); −0.0084 (2.10)

No. Ib-13, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

9.0780 (1.32); 9.0568 (1.36); 8.6799 (1.57); 8.6753 (2.45); 8.6706 (1.64); 8.4021 (0.99); 8.4000 (1.12); 8.3965 (1.03); 8.3943 (1.01); 8.3817 (1.10); 8.3795 (1.17); 8.3760 (1.13); 8.3738 (1.05); 8.3291 (0.60); 8.3069 (0.75); 8.2603 (1.40); 8.2403 (1.53); 8.1683 (0.69); 8.1545 (1.36); 8.1407 (0.73); 8.0530 (0.70); 8.0281 (2.99); 8.0231 (3.08); 8.0000 (0.35); 7.8454 (3.03); 7.8402 (3.22); 7.8344 (0.65); 7.7983 (1.57); 7.7862 (0.45); 7.7784 (2.70); 7.7583 (1.39); 7.7490 (0.33); 4.6852 (0.40); 4.6730 (0.49); 4.6603 (0.71); 4.6512 (0.67); 4.6390 (0.58); 4.6266 (0.48); 3.9162 (0.71); 3.9054 (3.69); 3.8649 (16.00); 3.8213 (1.05); 3.3927 (0.57); 3.3496 (216.43); 3.3122 (0.42); 3.1753 (0.99); 3.1622 (1.00); 3.1508 (0.50); 3.1323 (1.24); 3.1141 (1.80); 3.0998 (1.82); 3.0820 (1.61); 3.0730 (0.91); 3.0633 (0.67); 3.0499 (1.20); 3.0385 (1.09); 2.9682 (1.03); 2.9603 (0.36); 2.9427 (1.01); 2.9338 (0.83); 2.9081 (0.60); 2.6732 (0.41); 2.6689 (0.32); 2.5436 (0.36); 2.5264 (1.42); 2.5130 (23.96); 2.5087 (47.10); 2.5042 (62.08); 2.4997 (46.70); 2.4953 (23.70); 2.3310 (0.39); 1.0256 (4.45); 1.0076 (9.29); 0.9895 (4.28); 0.0079 (1.01); −0.0002 (28.58); −0.0085 (1.15)

No. Ib-14, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.9422 (1.43); 8.9209 (1.46); 8.1610 (2.48); 8.1363 (1.44); 8.1160 (1.50); 8.0955 (1.46); 8.0288 (2.69); 8.0239 (2.86); 7.9215 (1.16); 7.9022 (1.40); 7.8486 (3.05); 7.8436 (2.94); 7.7377 (1.07); 7.7182 (1.82); 7.6987 (0.82); 4.6651 (0.42); 4.6532 (0.51); 4.6401 (0.73); 4.6316 (0.70); 4.6186 (0.55); 4.6064 (0.44); 3.9052 (1.22); 3.8643 (16.00); 3.4142 (0.61); 3.3555 (340.93); 3.1471 (0.45); 3.1289 (1.16); 3.1109 (1.69); 3.0967 (1.72); 3.0791 (1.62); 3.0692 (0.88); 3.0610 (0.57); 3.0466 (1.22); 3.0349 (1.02); 2.9529 (1.05); 2.9270 (1.04); 2.9185 (0.77); 2.8926 (0.64); 2.6779 (0.36); 2.6734 (0.51); 2.6690 (0.39); 2.5264 (1.85); 2.5088 (59.40); 2.5043 (78.01); 2.4999 (60.22); 2.3353 (0.37); 2.3311 (0.49); 2.3266 (0.39); 1.0241 (3.87); 1.0061 (8.14); 0.9880 (3.75); 0.0079 (1.02); −0.0002 (26.03); −0.0084 (1.39)

No. Ib-16, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.4798 (1.13); 8.4584 (1.17); 8.0295 (2.43); 8.0245 (2.77); 8.0135 (0.99); 8.0018 (0.93); 7.8354 (2.64); 7.8303 (2.67); 7.8187 (3.54); 7.8137 (1.26); 7.8015 (1.18); 7.7965 (3.83); 7.7893 (0.67); 7.0036 (0.40); 6.9966 (3.76); 6.9920 (1.40); 6.9792 (1.13); 6.9744 (3.68); 4.6138 (0.35); 4.6028 (0.40); 4.5878 (0.60); 4.5814 (0.54); 4.5771 (0.49); 4.5663 (0.44); 4.5549 (0.37); 3.9047 (1.74); 3.8626 (14.76); 3.8018 (16.00); 3.3632 (276.64); 3.2965 (0.46); 3.1750 (0.73); 3.1619 (0.69); 3.0520 (0.49); 3.0409 (0.56); 3.0173 (0.93); 3.0063 (0.82); 2.9486 (0.89); 2.9221 (0.90); 2.9142 (0.62); 2.8875 (0.53); 2.7614 (0.32); 2.7501 (0.33); 2.6781 (0.32); 2.6736 (0.44); 2.6688 (0.33); 2.6175 (5.51); 2.6060 (5.57); 2.5267 (1.28); 2.5134 (23.37); 2.5090 (46.94); 2.5044 (62.47); 2.4998 (46.91); 2.4954 (23.71); 2.3311 (0.41); −0.0002 (8.81); −0.0085 (0.33)

No. Ib-17, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.7458 (1.28); 8.7244 (1.32); 8.0523 (1.00); 8.0408 (1.04); 8.0245 (2.71); 8.0195 (2.83); 7.8547 (1.05); 7.8484 (3.91); 7.8439 (1.48); 7.8302 (4.29); 7.8266 (6.63); 7.5593 (0.59); 7.5531 (4.64); 7.5485 (1.68); 7.5456 (1.30); 7.5362 (1.39); 7.5316 (4.14); 7.5242 (1.04); 4.6308 (0.39); 4.6196 (0.46); 4.6047 (0.68); 4.5984 (0.63); 4.5936 (0.56); 4.5833 (0.50); 4.5721 (0.43); 3.9051 (1.64); 3.8649 (16.00); 3.3508 (201.96); 3.3106 (0.39); 3.1750 (0.33); 3.1619 (0.33); 3.0725 (0.61); 3.0612 (0.68); 3.0378 (0.98); 3.0269 (0.91); 2.9392 (0.97); 2.9126 (0.99); 2.9047 (0.75); 2.8781 (0.62); 2.7819 (1.26); 2.7705 (1.26); 2.6730 (0.41); 2.6684 (0.33); 2.6200 (6.12); 2.6086 (6.22); 2.5431 (0.32); 2.5263 (1.23); 2.5127 (21.10); 2.5084 (42.38); 2.5039 (56.72); 2.4994 (43.28); 2.4952 (22.48); 2.3308 (0.37); 0.0079 (0.55); −0.0002 (15.44); −0.0085 (0.60)

No. Ib-19, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.6395 (1.24); 8.6180 (1.28); 8.0415 (3.06); 8.0364 (3.32); 7.8506 (2.78); 7.8456 (2.71); 7.8333 (0.67); 7.8248 (2.81); 7.8163 (0.79); 7.8121 (1.14); 7.8072 (3.23); 7.8035 (2.48); 7.5435 (0.65); 7.5314 (0.54); 7.5253 (1.75); 7.5198 (0.66); 7.5102 (0.98); 7.5070 (1.47); 7.4722 (2.61); 7.4530 (3.46); 7.4354 (1.40); 4.6402 (0.39); 4.6293 (0.45); 4.6138 (0.66); 4.6078 (0.61); 4.6029 (0.54); 4.5924 (0.50); 4.5813 (0.41); 3.9168 (0.32); 3.9053 (1.31); 3.8643 (16.00); 3.3427 (95.11); 3.0750 (0.57); 3.0639 (0.63); 3.0404 (1.00); 3.0294 (0.93); 2.9599 (1.03); 2.9332 (1.00); 2.9255 (0.70); 2.8987 (0.60); 2.7860 (0.94); 2.7746 (0.93); 2.6723 (0.38); 2.6235 (6.01); 2.6120 (6.08); 2.5257 (1.19); 2.5121 (22.21); 2.5078 (43.72); 2.5032 (57.55); 2.4987 (43.42); 2.4944 (22.25); 2.3681 (1.03); 2.3300 (0.39); 0.0080 (0.99); −0.0002 (28.08); −0.0085 (1.11)

No. Ib-21, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.9695 (1.24); 8.9479 (1.29); 8.1545 (2.08); 8.1069 (1.22); 8.0869 (2.19); 8.0752 (1.07); 8.0267 (2.48); 8.0217 (2.73); 7.9210 (1.05); 7.9014 (1.27); 7.8465 (2.92); 7.8414 (2.89); 7.7368 (1.01); 7.7171 (1.71); 7.6976 (0.79); 4.6676 (0.38); 4.6564 (0.44); 4.6415 (0.63); 4.6350 (0.60); 4.6199 (0.47); 4.6086 (0.41); 3.9053 (1.50); 3.8614 (16.00); 3.3939 (0.45); 3.3490 (290.87); 3.3092 (0.64); 3.2958 (0.38); 3.1100 (0.62); 3.0987 (0.69); 3.0751 (0.94); 3.0639 (0.86); 2.9455 (0.91); 2.9189 (0.94); 2.9111 (0.73); 2.8844 (0.65); 2.8167 (1.36); 2.8053 (1.36); 2.6775 (0.44); 2.6729 (0.61); 2.6684 (0.45); 2.6275 (5.97); 2.6161 (6.07); 2.5263 (1.78); 2.5215 (2.70); 2.5128 (31.36); 2.5084 (63.47); 2.5038 (84.85); 2.4992 (64.40); 2.4948 (32.96); 2.3350 (0.39); 2.3306 (0.54); 2.3259 (0.41); 0.0080 (1.06); −0.0002 (31.60); −0.0085 (1.22)

No. Ib-22, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

9.0341 (1.33); 9.0124 (1.36); 8.0081 (2.52); 8.0031 (2.63); 7.9140 (0.98); 7.9018 (0.98); 7.8032 (2.87); 7.7981 (2.73); 7.4588 (1.79); 7.4526 (2.49); 7.4357 (5.98); 7.4108 (3.01); 7.3952 (1.47); 7.3872 (0.98); 7.3715 (0.77); 4.6991 (0.41); 4.6880 (0.50); 4.6740 (0.71); 4.6660 (0.67); 4.6526 (0.53); 4.6405 (0.43); 3.9268 (0.34); 3.9165 (0.58); 3.9001 (16.00); 3.4522 (0.39); 3.4401 (0.53); 3.4313 (0.61); 3.3563 (474.53); 3.1741 (0.53); 3.1610 (0.48); 2.9868 (0.63); 2.9753 (0.68); 2.9513 (0.96); 2.9403 (0.87); 2.8399 (0.95); 2.8137 (0.99); 2.8048 (0.75); 2.7787 (0.66); 2.6773 (0.59); 2.6726 (0.80); 2.6683 (0.64); 2.6431 (6.26); 2.6315 (6.25); 2.5428 (0.54); 2.5258 (2.45); 2.5122 (43.02); 2.5081 (83.08); 2.5036 (108.82); 2.4991 (82.09); 2.4951 (42.14); 2.3691 (2.06); 2.3347 (0.55); 2.3303 (0.72); 2.3260 (0.54); 0.0079 (1.19); −0.0002 (32.40); −0.0084 (1.36)

No. Ib-23, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.6987 (1.44); 8.6774 (1.48); 8.0542 (3.80); 8.0496 (3.59); 8.0417 (1.36); 7.9331 (3.68); 7.9120 (4.79); 7.8633 (3.15); 7.8583 (3.05); 7.7810 (4.76); 7.7760 (2.35); 7.7599 (3.87); 7.7547 (1.45); 7.7460 (2.54); 7.7427 (3.55); 7.7246 (3.89); 7.5140 (1.89); 7.4957 (4.08); 7.4763 (2.61); 7.4284 (1.54); 7.4102 (2.00); 7.3919 (0.69); 4.6700 (0.41); 4.6586 (0.47); 4.6433 (0.72); 4.6375 (0.66); 4.6221 (0.51); 4.6109 (0.44); 3.9051 (3.70); 3.8681 (16.00); 3.4085 (0.33); 3.4016 (0.39); 3.3887 (0.75); 3.3489 (271.39); 3.3009 (0.38); 3.0919 (0.58); 3.0808 (0.67); 3.0571 (1.05); 3.0466 (0.95); 2.9791 (1.00); 2.9525 (1.04); 2.9448 (0.75); 2.9180 (0.60); 2.8110 (1.37); 2.7997 (1.39); 2.6772 (0.44); 2.6728 (0.59); 2.6684 (0.47); 2.6352 (6.31); 2.6237 (6.34); 2.5431 (0.43); 2.5259 (1.88); 2.5081 (66.01); 2.5036 (86.70); 2.4992 (66.22); 2.3347 (0.42); 2.3302 (0.56); 2.3261 (0.42); 0.0080 (1.11); −0.0002 (31.01); −0.0084 (1.35)

No. Ib-24, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.6898 (1.32); 8.6684 (1.34); 8.0175 (2.45); 8.0125 (2.61); 7.9650 (1.00); 7.9533 (0.99); 7.8234 (2.83); 7.8183 (2.72); 7.6525 (0.38); 7.6324 (0.47); 7.6169 (1.58); 7.6150 (1.67); 7.5973 (1.86); 7.5952 (1.84); 7.4405 (0.74); 7.4380 (0.78); 7.4219 (1.93); 7.4195 (1.95); 7.4036 (1.63); 7.4010 (1.54); 7.3862 (0.35); 7.3811 (0.58); 7.3661 (0.57); 7.3613 (1.24); 7.3568 (1.22); 7.3418 (1.43); 7.3374 (1.47); 7.3230 (0.75); 7.3184 (0.65); 7.2901 (1.65); 7.2858 (1.52); 7.2715 (1.33); 7.2672 (1.16); 4.6353 (0.40); 4.6243 (0.47); 4.6098 (0.67); 4.6024 (0.64); 4.5881 (0.49); 4.5770 (0.41); 3.9163 (0.43); 3.9037 (16.00); 3.3464 (193.76); 3.3056 (0.33); 3.0340 (0.64); 3.0230 (0.71); 2.9992 (0.90); 2.9882 (0.84); 2.8336 (0.89); 2.8074 (0.96); 2.7988 (0.76); 2.7727 (0.67); 2.7474 (1.80); 2.7357 (1.81); 2.6765 (0.36); 2.6720 (0.49); 2.6676 (0.41); 2.6625 (0.32); 2.6494 (6.07); 2.6379 (6.11); 2.5252 (1.37); 2.5074 (49.14); 2.5029 (64.74); 2.4985 (49.24); 2.3725 (0.39); 2.3296 (0.41); 0.0079 (0.86); −0.0002 (25.17); −0.0085 (1.11)

No. Ib-25, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.8661 (1.30); 8.8463 (1.31); 8.0392 (2.43); 8.0342 (2.61); 7.8950 (2.84); 7.8898 (2.67); 7.7992 (2.71); 7.7817 (3.25); 7.7779 (2.45); 7.5649 (0.52); 7.5617 (0.34); 7.5527 (0.38); 7.5467 (1.63); 7.5413 (0.51); 7.5315 (0.86); 7.5284 (1.36); 7.5252 (0.72); 7.4909 (2.41); 7.4718 (3.41); 7.4540 (1.42); 4.6810 (0.42); 4.6671 (0.52); 4.6614 (0.54); 4.6558 (0.66); 4.6474 (0.59); 4.6419 (0.56); 4.6361 (0.59); 4.6222 (0.46); 4.1404 (0.58); 4.1334 (0.77); 4.1226 (1.88); 4.1160 (1.98); 4.1048 (2.07); 4.0984 (1.87); 4.0870 (0.75); 4.0808 (0.59); 3.9049 (1.54); 3.8789 (16.00); 3.8558 (1.43); 3.3958 (0.33); 3.3719 (1.20); 3.3424 (214.24); 3.3091 (0.58); 3.1740 (0.38); 3.1670 (0.58); 3.1611 (0.42); 3.1534 (0.66); 3.1323 (1.08); 3.1186 (0.98); 3.0684 (1.05); 3.0431 (1.04); 3.0335 (0.63); 3.0082 (0.61); 2.6764 (0.45); 2.6719 (0.62); 2.6674 (0.48); 2.5422 (0.62); 2.5253 (2.03); 2.5204 (3.13); 2.5117 (36.22); 2.5073 (72.41); 2.5028 (96.50); 2.4983 (72.77); 2.4939 (37.02); 2.3340 (0.45); 2.3296 (0.62); 2.3250 (0.45); 1.1692 (4.11); 1.1515 (8.68); 1.1337 (4.00); 0.0080 (0.95); −0.0002 (29.70); −0.0085 (1.23)

No. Ib-26, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.7059 (1.18); 8.6862 (1.21); 8.0300 (2.23); 8.0249 (2.49); 7.8833 (2.52); 7.8782 (2.47); 7.8063 (0.41); 7.7991 (3.52); 7.7941 (1.34); 7.7819 (1.26); 7.7769 (3.93); 7.0211 (0.39); 7.0139 (3.71); 7.0090 (1.29); 6.9917 (3.80); 6.9848 (0.53); 6.9721 (0.43); 4.6475 (0.36); 4.6337 (0.46); 4.6281 (0.48); 4.6226 (0.60); 4.6142 (0.53); 4.6089 (0.52); 4.6031 (0.55); 4.5889 (0.40); 4.1302 (0.51); 4.1225 (0.75); 4.1124 (1.74); 4.1051 (1.91); 4.0945 (1.96); 4.0875 (1.79); 4.0770 (0.80); 4.0698 (0.58); 4.0604 (0.33); 3.9051 (1.06); 3.8771 (15.24); 3.8536 (1.79); 3.8064 (16.00); 3.7952 (2.16); 3.3428 (133.18); 3.1472 (0.54); 3.1333 (0.58); 3.1123 (1.04); 3.0986 (0.92); 3.0577 (0.95); 3.0324 (0.95); 3.0229 (0.59); 2.9975 (0.55); 2.6765 (0.37); 2.6719 (0.55); 2.6675 (0.42); 2.5253 (1.46); 2.5206 (2.35); 2.5119 (29.81); 2.5075 (61.46); 2.5029 (83.10); 2.4984 (63.59); 2.4940 (33.08); 2.3343 (0.45); 2.3297 (0.60); 2.3251 (0.47); 1.2337 (0.33); 1.1621 (4.05); 1.1443 (8.60); 1.1266 (3.94); 0.0081 (1.26); −0.0002 (41.65); −0.0084 (1.87)

No. Ib-28, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

9.1636 (1.35); 9.1440 (1.36); 8.1192 (2.21); 8.1047 (1.32); 8.0846 (1.34); 8.0358 (2.56); 8.0308 (2.91); 7.9487 (1.08); 7.9290 (1.30); 7.9016 (3.05); 7.8965 (2.83); 7.7604 (1.02); 7.7409 (1.71); 7.7215 (0.82); 4.7215 (0.44); 4.7072 (0.55); 4.7023 (0.59); 4.6969 (0.68); 4.6879 (0.61); 4.6827 (0.60); 4.6775 (0.64); 4.6633 (0.46); 4.1486 (0.60); 4.1412 (0.80); 4.1307 (1.90); 4.1239 (1.99); 4.1129 (2.06); 4.1063 (1.89); 4.0952 (0.80); 4.0886 (0.62); 3.9052 (1.46); 3.8981 (0.54); 3.8773 (16.00); 3.8533 (2.03); 3.3378 (153.38); 3.1866 (0.69); 3.1734 (0.97); 3.1610 (0.46); 3.1518 (1.17); 3.1379 (1.06); 3.0726 (1.04); 3.0477 (1.04); 3.0380 (0.69); 3.0128 (0.61); 2.6764 (0.63); 2.6719 (0.88); 2.6675 (0.67); 2.5422 (0.88); 2.5252 (2.88); 2.5116 (48.87); 2.5073 (97.47); 2.5028 (129.89); 2.4983 (98.96); 2.4941 (51.62); 2.3341 (0.60); 2.3296 (0.83); 2.3250 (0.61); 1.2340 (0.40); 1.1692 (4.17); 1.1515 (8.67); 1.1338 (4.02); 0.0080 (2.02); −0.0002 (60.25); −0.0084 (2.75)

No. Ib-29, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

9.1954 (1.30); 9.1746 (1.34); 8.0381 (2.34); 8.0330 (2.52); 7.8784 (2.75); 7.8732 (2.64); 7.4792 (1.56); 7.4733 (2.21); 7.4561 (5.33); 7.4430 (0.55); 7.4294 (2.83); 7.4135 (1.17); 7.4058 (0.92); 7.3900 (0.80); 4.8001 (0.43); 4.7882 (0.51); 4.7794 (0.51); 4.7734 (0.66); 4.7674 (0.63); 4.7618 (0.54); 4.7527 (0.55); 4.7409 (0.45); 4.1860 (0.34); 4.1769 (0.52); 4.1669 (0.75); 4.1591 (1.75); 4.1490 (1.84); 4.1412 (1.93); 4.1312 (1.73); 4.1230 (0.84); 4.1135 (0.58); 4.1042 (0.37); 3.9045 (2.70); 3.9001 (16.00); 3.8806 (1.15); 3.3346 (86.46); 3.3078 (0.32); 3.1589 (0.71); 3.1464 (0.73); 3.1227 (0.89); 3.1113 (0.88); 2.9215 (0.89); 2.8948 (0.91); 2.8861 (0.76); 2.8593 (0.68); 2.6759 (0.45); 2.6712 (0.64); 2.6666 (0.48); 2.5414 (0.37); 2.5245 (2.01); 2.5196 (3.04); 2.5110 (35.89); 2.5066 (72.87); 2.5021 (97.93); 2.4975 (74.69); 2.4932 (38.68); 2.3335 (0.45); 2.3289 (0.64); 2.3242 (0.49); 1.2346 (0.33); 1.2189 (4.13); 1.2011 (8.73); 1.1834 (4.07); 0.0080 (1.82); −0.0002 (56.52); −0.0084 (2.53)

No. Ib-30, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.9351 (1.28); 8.9149 (1.29); 8.0433 (2.39); 8.0382 (2.57); 7.8890 (2.88); 7.8838 (2.64); 7.6469 (1.49); 7.6446 (1.56); 7.6270 (1.77); 7.6247 (1.76); 7.4629 (0.62); 7.4602 (0.67); 7.4442 (1.66); 7.4415 (1.69); 7.4256 (1.21); 7.4227 (1.22); 7.3833 (1.01); 7.3788 (1.14); 7.3638 (1.27); 7.3592 (1.39); 7.3447 (0.65); 7.3403 (0.63); 7.2150 (1.52); 7.2106 (1.55); 7.1963 (1.35); 7.1920 (1.28); 4.6796 (0.43); 4.6666 (0.52); 4.6592 (0.52); 4.6535 (0.65); 4.6466 (0.61); 4.6407 (0.55); 4.6333 (0.56); 4.6205 (0.44); 4.1711 (0.59); 4.1665 (0.68); 4.1533 (1.94); 4.1488 (2.02); 4.1354 (2.09); 4.1312 (1.98); 4.1176 (0.73); 4.1135 (0.68); 3.9085 (16.00); 3.8791 (1.63); 3.3344 (76.80); 3.1562 (0.72); 3.1436 (0.76); 3.1211 (0.92); 3.1085 (0.85); 2.9544 (0.93); 2.9283 (0.93); 2.9192 (0.74); 2.8931 (0.66); 2.6758 (0.46); 2.6711 (0.63); 2.6666 (0.46); 2.5414 (0.39); 2.5246 (2.00); 2.5197 (3.00); 2.5110 (35.62); 2.5066 (71.89); 2.5021 (96.27); 2.4976 (72.83); 2.4932 (37.31); 2.3331 (0.45); 2.3289 (0.63); 2.3244 (0.47); 1.2345 (0.37); 1.2187 (4.11); 1.2010 (8.65); 1.1832 (4.02); 0.0080 (1.80); −0.0002 (56.41); −0.0085 (2.45)

No. Ib-32, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.9265 (1.50); 8.9067 (1.52); 8.0520 (2.80); 8.0469 (2.87); 8.0333 (0.53); 7.9113 (6.23); 7.9064 (4.20); 7.8900 (4.65); 7.8456 (0.51); 7.8243 (0.49); 7.7965 (4.81); 7.7754 (3.46); 7.7701 (1.12); 7.7586 (0.42); 7.7548 (0.56); 7.7474 (2.44); 7.7441 (3.11); 7.7262 (3.55); 7.7099 (0.46); 7.5172 (1.75); 7.4992 (3.66); 7.4798 (2.28); 7.4328 (1.41); 7.4145 (1.84); 7.3962 (0.62); 4.7105 (0.43); 4.6963 (0.53); 4.6908 (0.58); 4.6853 (0.71); 4.6770 (0.61); 4.6715 (0.59); 4.6659 (0.60); 4.6518 (0.46); 4.3495 (0.44); 4.3317 (0.44); 4.1526 (0.60); 4.1455 (0.81); 4.1347 (1.97); 4.1283 (2.05); 4.1168 (2.09); 4.1107 (1.98); 4.0991 (0.82); 4.0931 (0.62); 3.9048 (1.77); 3.8975 (0.34); 3.8828 (16.00); 3.8574 (1.67); 3.4020 (0.77); 3.3495 (396.68); 3.3019 (0.52); 3.2926 (0.33); 3.1844 (0.58); 3.1704 (0.75); 3.1616 (0.37); 3.1491 (1.12); 3.1357 (0.96); 3.0907 (1.03); 3.0655 (1.04); 3.0560 (0.67); 3.0307 (0.58); 2.6770 (0.53); 2.6725 (0.73); 2.6681 (0.55); 2.5425 (0.46); 2.5256 (2.44); 2.5119 (43.79); 2.5079 (86.57); 2.5034 (114.86); 2.4989 (87.47); 2.4948 (45.39); 2.3345 (0.56); 2.3301 (0.76); 2.3257 (0.55); 1.3616 (0.46); 1.3438 (0.99); 1.3260 (0.49); 1.2335 (0.40); 1.1795 (4.19); 1.1617 (8.75); 1.1440 (4.08); 0.0080 (1.35); −0.0002 (42.89); −0.0085 (1.96)

No. Ib-47, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8,71 (11,84); 8,6412 (1,72); 8,627 (3,39); 8,6129 (1,72); 8,1225 (16); 7,7682 (4,09); 7,7487 (5,54); 7,7348 (1,85); 7,7163 (4,7); 7,6976 (3,3); 7,6519 (3,32); 7,6328 (4,22); 7,6137 (1,55); 7,4483 (4,9); 7,4295 (4,28); 4,056 (0,42); 4,0381 (1,33); 4,0203 (1,34); 4,0026 (0,46); 3,6184 (2,6); 3,6021 (7,21); 3,5866 (7,43); 3,5705 (2,9); 3,3223 (81,02); 3,0794 (4,88); 3,0628 (9,46); 3,0462 (4,26); 2,6754 (0,54); 2,6709 (0,75); 2,6664 (0,54); 2,541 (0,34); 2,5242 (2,53); 2,5193 (3,97); 2,5109 (43,46); 2,5064 (86,25); 2,5018 (112,35); 2,4972 (79,7); 2,4927 (37,52); 2,3331 (0,55); 2,3286 (0,74); 2,324 (0,54); 1,9889 (5,92); 1,336 (0,32); 1,2497 (0,43); 1,1928 (1,6); 1,175 (3,17); 1,1572 (1,57); 0,146 (0,42); 0,008 (3,8); −0,0002 (102,72); −0,0085 (3,28); −0,1497 (0,44)

No. Ib-48, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8,6827 (12,03); 8,4604 (1,46); 8,4481 (2,66); 8,4349 (1,47); 8,3168 (0,32); 8,1057 (16); 7,5365 (5,11); 7,5205 (6,84); 7,5175 (8,28); 7,5025 (5,08); 7,4981 (4,67); 7,4849 (2); 7,4804 (1,11); 7,2896 (3,19); 7,2772 (4); 7,2749 (4,11); 7,2699 (3,14); 7,2642 (4,2); 7,2579 (7,4); 7,24 (5,58); 3,6166 (2,62); 3,6008 (7,34); 3,5851 (7,57); 3,5692 (2,96); 3,3244 (32,92); 3,1008 (5,22); 3,0845 (9,74); 3,0681 (4,58); 2,6721 (0,39); 2,5254 (1,12); 2,5205 (1,8); 2,512 (22,07); 2,5076 (43,98); 2,503 (57,42); 2,4985 (41,01); 2,494 (19,58); 2,3298 (0,37); 1,9896 (1,03); 1,3371 (0,32); 1,2501 (0,39); 1,1757 (0,55); 0,0079 (1,96); −0,0002 (53,1); −0,0085 (1,74)

No. Ib-49, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8,7171 (12); 8,5614 (1,7); 8,5469 (3,3); 8,5325 (1,68); 8,1125 (16); 7,4807 (2,72); 7,477 (3,64); 7,4609 (6,5); 7,4574 (7,22); 7,444 (3,26); 7,4393 (3,54); 7,4264 (5,28); 7,4217 (5,43); 7,407 (2,8); 7,4019 (3,2); 7,3943 (3,03); 7,3902 (2,8); 7,3756 (5,88); 7,3719 (5,67); 7,358 (3,56); 7,3543 (3,3); 7,3423 (7,15); 7,3376 (6,18); 7,3237 (3,58); 7,3189 (2,63); 4,0384 (0,37); 4,0206 (0,37); 3,6198 (2,7); 3,604 (7,27); 3,5882 (7,4); 3,5723 (3,02); 3,3231 (38,85); 3,092 (5,02); 3,0757 (9,22); 3,0595 (4,42); 2,6711 (0,42); 2,5244 (1,25); 2,5196 (2); 2,5111 (24,27); 2,5066 (48,3); 2,502 (62,98); 2,4975 (44,73); 2,493 (21,09); 2,3288 (0,41); 1,9891 (1,61); 1,1931 (0,44); 1,1753 (0,86); 1,1575 (0,43); 0,0079 (2,25); −0,0002 (59,88); −0,0085 (1,86)

No. Ib-50, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8,7483 (1,69); 8,7342 (3,34); 8,7195 (1,74); 8,6992 (12,09); 8,3167 (0,59); 8,1159 (16); 7,7065 (2,33); 7,6992 (2,97); 7,684 (4,34); 7,646 (1,05); 7,641 (1,56); 7,6274 (5,27); 7,6224 (7,45); 7,6133 (7,34); 7,6046 (7,28); 7,5998 (3,97); 7,586 (1,12); 7,5811 (0,8); 7,5239 (3,85); 7,5161 (1,96); 7,5095 (2,84); 7,5023 (2,23); 7,2782 (3,52); 7,1391 (7,94); 6,9999 (3,89); 3,6308 (2,55); 3,6153 (6,9); 3,5993 (7,01); 3,5837 (2,88); 3,3231 (37,97); 3,1043 (4,91); 3,0881 (8,87); 3,072 (4,35); 2,6757 (0,35); 2,6713 (0,48); 2,6667 (0,34); 2,5247 (1,35); 2,5198 (2,15); 2,5112 (27,33); 2,5068 (54,91); 2,5022 (72,12); 2,4976 (51,68); 2,4931 (24,6); 2,3334 (0,35); 2,329 (0,48); 2,3242 (0,34); 1,9891 (0,8); 1,3364 (0,36); 1,2497 (0,44); 1,1752 (0,44); 0,0079 (2,52); −0,0002 (71,05); −0,0086 (2,3)

No. Ib-51, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8,8402 (1,65); 8,8259 (3,17); 8,8113 (1,61); 8,6709 (11,61); 8,3159 (0,68); 8,1132 (16); 7,533 (1,12); 7,5163 (2,4); 7,5117 (2,16); 7,4996 (1,58); 7,4951 (4,56); 7,4908 (1,64); 7,4784 (2,2); 7,474 (2,67); 7,4574 (1,21); 7,1788 (0,92); 7,1756 (1,29); 7,1683 (7,79); 7,1486 (10,07); 7,1282 (6,58); 7,1206 (1,09); 3,6314 (2,61); 3,6156 (7,08); 3,5998 (7,25); 3,584 (2,94); 3,3218 (62,92); 3,0811 (4,99); 3,0648 (9,2); 3,0484 (4,38); 2,6753 (0,51); 2,6709 (0,69); 2,6662 (0,5); 2,5242 (2,16); 2,5108 (38,97); 2,5063 (78,04); 2,5018 (102,47); 2,4972 (73,54); 2,4927 (35,05); 2,3331 (0,49); 2,3286 (0,67); 2,3241 (0,49); 1,9888 (0,79); 1,2497 (0,38); 1,1751 (0,42); 0,1459 (0,41); 0,008 (3,43); −0,0002 (95,23); −0,0085 (3,18); −0,1497 (0,42)

No. Ib-52, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8,735 (12,42); 8,5559 (1,8); 8,5414 (3,47); 8,5272 (1,75); 8,1151 (16); 7,6382 (5,43); 7,6359 (5,64); 7,6185 (6,39); 7,6159 (6,32); 7,4387 (2,21); 7,4359 (2,37); 7,4201 (6,17); 7,4173 (6,15); 7,4016 (5); 7,3986 (4,62); 7,3614 (3,67); 7,3567 (4,91); 7,342 (4,58); 7,3372 (6,02); 7,3228 (2,52); 7,3182 (2,79); 7,3121 (6,94); 7,3076 (5,55); 7,2936 (5,02); 7,2891 (4,16); 4,0381 (0,77); 4,0203 (0,79); 3,6118 (2,76); 3,596 (7,53); 3,5802 (7,71); 3,5643 (3,07); 3,3227 (57,87); 3,0933 (5,24); 3,077 (9,76); 3,0606 (4,57); 2,6754 (0,43); 2,6708 (0,59); 2,6663 (0,44); 2,5241 (1,89); 2,5108 (34,46); 2,5063 (68,68); 2,5018 (89,88); 2,4972 (64,22); 2,4927 (30,4); 2,333 (0,41); 2,3285 (0,58); 2,3238 (0,41); 1,9889 (3,37); 1,2496 (0,4); 1,1929 (0,92); 1,1751 (1,84); 1,1573 (0,89); 0,1458 (0,36); 0,0079 (3,22); −0,0002 (86,56); −0,0086 (2,66); −0,1498 (0,37)

No. Ib-53, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8,6073 (1,8); 8,593 (3,58); 8,5783 (1,81); 8,4839 (12,08); 8,1481 (16); 7,7765 (4,12); 7,7568 (5,61); 7,7426 (1,86); 7,7239 (4,66); 7,7053 (3,28); 7,6591 (3,26); 7,64 (4,2); 7,621 (1,54); 7,4957 (4,97); 7,477 (4,24); 3,6068 (2,39); 3,5914 (6,39); 3,5755 (6,56); 3,56 (2,64); 3,321 (52,6); 2,9483 (4,62); 2,9322 (8,3); 2,9163 (4,2); 2,6746 (0,75); 2,6702 (1,04); 2,6657 (0,79); 2,5055 (121,35); 2,5011 (159,35); 2,4966 (118,42); 2,3323 (0,8); 2,3278 (1,09); 2,3235 (0,84); 0,0079 (2,63); −0,0002 (67,13); −0,0084 (2,64)

No. Ib-54, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8,5344 (1,76); 8,5199 (3,45); 8,5052 (1,8); 8,4841 (12,28); 8,1391 (16); 7,4886 (3,29); 7,4696 (8,29); 7,4508 (2,72); 7,4424 (3,04); 7,4369 (3,7); 7,4285 (4,71); 7,422 (1,4); 7,4182 (2,28); 7,4087 (3,08); 7,4039 (1,31); 7,4003 (1,51); 7,3849 (6,98); 7,3809 (9,79); 7,3711 (9,42); 7,3694 (8,95); 7,3612 (0,97); 5,7577 (0,78); 3,6096 (2,52); 3,5947 (6,25); 3,5787 (6,28); 3,5633 (2,68); 3,3226 (17,91); 2,9589 (4,78); 2,9429 (7,65); 2,9275 (4,26); 2,6704 (0,38); 2,5231 (1,48); 2,5101 (22,28); 2,5058 (43,23); 2,5013 (56,03); 2,4968 (40,53); 2,4924 (19,73); 2,328 (0,35); 0,0077 (1,19); −0,0002 (27,66); −0,0083 (0,95)

No. Ib-55, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz 8,5704 (2,81); 8,5566 (5,41); 8,5427 (2,81); 8,3833 (12,61); 8,379 (12,95); 7,7702 (6,68); 7,7507 (9,01); 7,7359 (13,52); 7,7291 (3,52); 7,7148 (16); 7,6915 (5,36); 7,6498 (5,33); 7,6308 (6,77); 7,6119 (2,49); 7,445 (7,93); 7,4263 (6,9); 7,2906 (7,56); 7,286 (7,73); 7,2696 (6,89); 7,265 (7,01); 5,7576 (9,66); 3,5338 (4,38); 3,5181 (11,17); 3,5024 (11,27); 3,4867 (4,7); 3,3245 (71,55); 2,8019 (8,21); 2,7855 (15,04); 2,7692 (7,46); 2,6752 (0,51); 2,6707 (0,7); 2,6661 (0,54); 2,5239 (2,59); 2,5106 (38,66); 2,5062 (77,48); 2,5016 (102,24); 2,4971 (75,05); 2,4927 (37,56); 2,3329 (0,47); 2,3284 (0,65); 2,3238 (0,48); 1,2357 (0,36); 1,1644 (0,44); 0,0079 (1,85); −0,0002 (49,42); −0,0085 (2)

No. Ib-56, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8,4973 (2,91); 8,4834 (5,5); 8,4696 (2,87); 8,3873 (13,9); 8,383 (13,77); 7,733 (14,28); 7,712 (15,72); 7,4828 (4,98); 7,4795 (6,03); 7,4629 (11,4); 7,46 (12,04); 7,4439 (5,46); 7,4391 (5,93); 7,4265 (8,95); 7,4216 (9,12); 7,4135 (0,61); 7,407 (4,7); 7,4017 (5,42); 7,3921 (4,94); 7,3882 (4,5); 7,3734 (10,12); 7,3698 (10,05); 7,3558 (6,62); 7,3523 (6,34); 7,3446 (12,51); 7,3396 (10,59); 7,3261 (5,43); 7,3211 (3,87); 7,3017 (8,41); 7,2971 (8,35); 7,2808 (7,62); 7,2761 (7,55); 5,756 (6,39); 3,5354 (5,05); 3,5201 (12,51); 3,504 (12,4); 3,4886 (5,35); 3,431 (0,33); 3,4159 (0,45); 3,41 (0,48); 3,3903 (0,78); 3,3444 (450,13); 3,3013 (0,54); 3,2882 (0,35); 2,8175 (9,11); 2,8012 (16); 2,7851 (8,34); 2,6764 (0,49); 2,6718 (0,68); 2,6673 (0,51); 2,5249 (2,28); 2,5116 (39,17); 2,5073 (77,08); 2,5027 (99,94); 2,4982 (71,55); 2,4937 (34,05); 2,3339 (0,45); 2,3294 (0,63); 2,3249 (0,44); 1,2345 (0,42); 1,1804 (0,38); 1,1661 (0,58); 0,0079 (2,09); −0,0002 (55,95); −0,0085 (1,74)

No. Ib-57, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8,7559 (12,12); 8,5226 (1,96); 8,508 (3,73); 8,4935 (1,86); 8,1191 (16); 7,873 (5,78); 7,8709 (6); 7,8533 (6,23); 7,8512 (6,09); 7,4503 (2,79); 7,4477 (2,86); 7,4315 (6,31); 7,4289 (6,32); 7,4128 (3,92); 7,4102 (3,8); 7,2493 (5,43); 7,2453 (6,19); 7,2303 (4,84); 7,2264 (4,86); 7,1761 (3,53); 7,1719 (3,31); 7,1568 (5,23); 7,1527 (4,84); 7,1378 (3,03); 7,1336 (2,7); 4,0378 (0,46); 4,02 (0,47); 3,5951 (2,67); 3,5789 (7,35); 3,5634 (7,56); 3,5473 (2,95); 3,3221 (35,97); 3,1008 (5,09); 3,0845 (9,62); 3,068 (4,37); 2,6796 (0,33); 2,6751 (0,63); 2,6705 (0,85); 2,666 (0,63); 2,5237 (3,84); 2,5105 (49,85); 2,5061 (96,07); 2,5015 (124,05); 2,4969 (89,44); 2,4925 (43,13); 2,3328 (0,61); 2,3282 (0,82); 2,3237 (0,58); 1,9889 (2,05); 1,2495 (0,37); 1,1924 (0,58); 1,1747 (1,11); 1,1568 (0,55); 0,008 (1,16); −0,0002 (26,92); −0,0085 (0,92)

No. Ib-58, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8,8309 (1,95); 8,8165 (3,81); 8,802 (1,9); 8,74 (12,45); 8,1262 (16); 8,0252 (5,3); 8,0227 (5,51); 8,005 (6,13); 8,0025 (6,06); 7,8045 (2,35); 7,802 (2,44); 7,7858 (5,97); 7,7831 (5,83); 7,767 (4,06); 7,7643 (3,8); 7,7061 (3,66); 7,7026 (3,99); 7,6865 (4,95); 7,6831 (5,22); 7,667 (2,39); 7,6636 (2,31); 7,544 (5,91); 7,5406 (5,92); 7,5252 (5,25); 7,5217 (4,92); 5,759 (0,69); 3,6065 (2,75); 3,5903 (7,6); 3,5748 (7,83); 3,5587 (3); 3,3276 (15,72); 3,0946 (5,19); 3,0781 (9,93); 3,0615 (4,49); 2,5254 (1,02); 2,5121 (16,86); 2,5078 (32,46); 2,5033 (41,79); 2,4987 (30,1); 2,4944 (14,48); 1,2349 (0,45); 0,0079 (0,61); −0,0002 (15,01); −0,0081 (0,47)

No. Ib-59, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8,4395 (2,05); 8,4271 (3,53); 8,4148 (2,01); 8,0663 (6,7); 8,0468 (8,84); 7,9199 (13,89); 7,9004 (10,87); 7,55 (2,51); 7,5458 (4,01); 7,537 (2,67); 7,5322 (5,59); 7,5275 (8,22); 7,5185 (4,54); 7,5164 (3,81); 7,5121 (4,94); 7,5081 (5,1); 7,5044 (4,9); 7,498 (4,2); 7,4932 (2,19); 7,4845 (2,72); 7,4799 (1,87); 7,2861 (4,8); 7,2773 (5,85); 7,2748 (5,7); 7,2651 (4,97); 7,2584 (16); 7,2388 (9,85); 3,6313 (3,64); 3,6153 (10,06); 3,5998 (10,35); 3,5839 (4,07); 3,5604 (0,33); 3,3245 (118,47); 3,0774 (6,8); 3,061 (12,97); 3,0446 (6,19); 2,6759 (0,65); 2,6714 (0,93); 2,6667 (0,66); 2,5248 (2,6); 2,52 (4,21); 2,5114 (50,63); 2,5069 (101,96); 2,5023 (135,03); 2,4977 (97,51); 2,4932 (46,2); 2,3337 (0,65); 2,329 (0,89); 2,3246 (0,65); 1,3362 (0,42); 1,2987 (0,71); 1,2588 (1); 1,2496 (0,45); 0,0079 (2,24); −0,0002 (64,63); −0,0086 (1,97)

No. Ib-60, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8,5326 (2,71); 8,5185 (5,3); 8,5041 (2,67); 8,1283 (7,82); 8,109 (9,69); 7,9488 (16); 7,9293 (13,14); 7,6361 (7,96); 7,6342 (8,92); 7,6168 (9,21); 7,6142 (9,76); 7,4365 (3,52); 7,4335 (3,78); 7,4272 (0,58); 7,4179 (10,04); 7,415 (8,8); 7,4087 (0,68); 7,4055 (0,7); 7,3994 (8,61); 7,3963 (7,91); 7,3603 (5,75); 7,3555 (8,7); 7,3412 (6,93); 7,3362 (11,78); 7,3267 (11,72); 7,322 (9,96); 7,317 (5,01); 7,3085 (7,94); 7,3042 (6,09); 5,7571 (0,4); 3,6279 (4,2); 3,6118 (11,36); 3,5964 (11,72); 3,5804 (4,68); 3,324 (93,87); 3,0758 (7,44); 3,0594 (14,17); 3,043 (6,62); 2,6756 (0,6); 2,671 (0,82); 2,6664 (0,59); 2,5244 (2,3); 2,5197 (3,52); 2,511 (44,16); 2,5065 (89,44); 2,5019 (118,65); 2,4973 (85,56); 2,4927 (40,42); 2,3333 (0,56); 2,3287 (0,78); 2,324 (0,55); 1,2587 (0,45); 1,2351 (0,69); 0,008 (2,12); −0,0002 (64,08); −0,0085 (1,93)

No. Ib-61, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8,4995 (3,2); 8,4854 (6,21); 8,4713 (3,15); 8,1467 (8,78); 8,1273 (10,62); 7,9524 (16); 7,9329 (13,42); 7,8696 (10,05); 7,8676 (10,3); 7,8498 (10,79); 7,8478 (10,48); 7,4473 (4,68); 7,4447 (4,79); 7,4285 (10,65); 7,4259 (10,54); 7,4098 (6,71); 7,4072 (6,44); 7,2649 (9,35); 7,261 (10,18); 7,246 (8,09); 7,2421 (7,87); 7,1743 (5,78); 7,1702 (5,48); 7,155 (8,68); 7,151 (7,99); 7,1361 (5,02); 7,1319 (4,5); 5,7569 (0,85); 3,6158 (4,46); 3,5996 (12,38); 3,5843 (12,87); 3,5682 (4,99); 3,3235 (85,29); 3,0832 (8,22); 3,0667 (15,87); 3,0502 (7,29); 2,6755 (0,71); 2,6709 (0,96); 2,6664 (0,69); 2,5241 (3,13); 2,5107 (54,99); 2,5064 (107,18); 2,5018 (139,98); 2,4973 (102,13); 2,4929 (49,36); 2,3332 (0,69); 2,3287 (0,95); 2,3241 (0,69); 2,3199 (0,33); 1,2986 (0,42); 1,2588 (0,56); 1,2496 (0,38); 1,2351 (0,45); 0,008 (2,63); −0,0002 (66,5); −0,0085 (2,19)

No. Ib-62, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8,5395 (2,58); 8,5252 (4,93); 8,5108 (2,52); 8,3923 (0,53); 8,1113 (7,36); 8,0919 (9,23); 8,0634 (0,35); 7,9415 (14,61); 7,933 (0,71); 7,922 (11,86); 7,8581 (0,39); 7,6527 (0,4); 7,6326 (0,46); 7,4791 (3,84); 7,476 (4,94); 7,4604 (8,27); 7,459 (9,64); 7,4569 (10,62); 7,4435 (5,17); 7,4381 (5,56); 7,4267 (8,35); 7,4212 (8,53); 7,4073 (4,11); 7,4014 (5,4); 7,3936 (3,92); 7,3897 (3,52); 7,3835 (1,14); 7,3748 (9,27); 7,3712 (9,59); 7,3551 (16); 7,351 (9,88); 7,3497 (9,36); 7,3371 (3,87); 7,332 (2,17); 7,2501 (0,41); 7,2307 (0,36); 3,6337 (3,97); 3,6177 (10,79); 3,6022 (11,12); 3,5863 (4,5); 3,5501 (0,37); 3,5347 (0,36); 3,3236 (83,87); 3,0733 (7,12); 3,0569 (13,42); 3,0407 (6,46); 2,6756 (0,6); 2,671 (0,82); 2,6664 (0,59); 2,5244 (2,32); 2,5196 (3,8); 2,511 (45,88); 2,5065 (92,41); 2,5019 (122,6); 2,4973 (89,05); 2,4928 (42,5); 2,3378 (0,33); 2,3331 (0,72); 2,3262 (1,59); 1,3361 (1,23); 1,2986 (0,73); 1,2587 (1,07); 1,2496 (1,57); 1,2347 (1,25); 0,008 (2,13); −0,0002 (60,39); −0,0085 (1,9)

No. Ib-63, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8,6202 (3); 8,6061 (5,74); 8,5918 (2,88); 8,1068 (8,17); 8,0874 (10,4); 7,9414 (16); 7,9219 (12,84); 7,7685 (6,9); 7,7491 (9,24); 7,7317 (3,07); 7,7131 (7,95); 7,6944 (5,65); 7,6513 (5,62); 7,6322 (7,06); 7,6132 (2,59); 7,4626 (8,39); 7,4438 (7,26); 3,6312 (4,41); 3,6148 (12,14); 3,5996 (12,53); 3,5834 (4,84); 3,3237 (93,22); 3,0608 (7,95); 3,0442 (15,43); 3,0276 (7,03); 2,6756 (0,8); 2,6711 (1,08); 2,6665 (0,78); 2,6621 (0,37); 2,5244 (3,4); 2,5111 (61,64); 2,5066 (119,84); 2,502 (155,26); 2,4974 (112,22); 2,4929 (53); 2,3377 (0,36); 2,3333 (0,76); 2,3288 (1,04); 2,3242 (0,73); 1,299 (0,36); 1,2588 (0,54); 0,0079 (2,86); −0,0002 (73,47); −0,0085 (2,4)

No. Ib-64, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8,8194 (2,58); 8,8053 (4,81); 8,791 (2,46); 8,3159 (0,39); 8,0717 (0,51); 8,0616 (7,23); 8,0422 (9,66); 7,932 (16); 7,9125 (12,14); 7,5319 (1,91); 7,5252 (0,33); 7,5153 (4,11); 7,5107 (3,36); 7,4987 (2,75); 7,4941 (7,6); 7,4897 (2,59); 7,4774 (3,53); 7,473 (4,46); 7,4564 (2,03); 7,2157 (0,33); 7,1754 (1,57); 7,1722 (2,09); 7,1649 (12,75); 7,1537 (2,1); 7,1455 (15,63); 7,1388 (2,76); 7,1355 (1,84); 7,1246 (10,66); 7,1171 (1,81); 4,056 (0,41); 4,0381 (1,25); 4,0203 (1,25); 4,0025 (0,42); 3,6494 (4,13); 3,6333 (11,08); 3,6179 (11,36); 3,6018 (4,59); 3,3239 (196,04); 3,061 (7,4); 3,0446 (14); 3,0281 (6,76); 2,8573 (1,13); 2,6802 (0,38); 2,6757 (0,8); 2,6711 (1,12); 2,6665 (0,81); 2,6618 (0,37); 2,5245 (3,38); 2,5197 (5,4); 2,5111 (62); 2,5066 (123,95); 2,502 (163,34); 2,4974 (116,58); 2,4928 (54,33); 2,3378 (0,38); 2,3333 (0,81); 2,3288 (1,12); 2,3242 (0,8); 2,3198 (0,36); 1,989 (5,63); 1,3361 (1,05); 1,2497 (1,36); 1,1929 (1,52); 1,1751 (3,06); 1,1573 (1,51); 0,9346 (0,32); 0,008 (1,37); −0,0002 (40,17); −0,0086 (1,16)

No. Ib-65, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8,3879 (3,25); 8,2878 (9,04); 8,2822 (9,29); 7,769 (6,03); 7,7628 (5,97); 7,7486 (6,92); 7,7423 (6,82); 7,535 (7,46); 7,519 (9,68); 7,516 (11,22); 7,5011 (6,87); 7,4991 (6,76); 7,4964 (6,5); 7,4921 (2,5); 7,4833 (3,07); 7,4787 (1,78); 7,4585 (11,12); 7,438 (9,73); 7,2896 (4,5); 7,2783 (5,72); 7,2758 (5,96); 7,27 (4,42); 7,2645 (5,82); 7,259 (10,08); 7,2574 (10,06); 7,2407 (9,4); 3,5267 (4,03); 3,5099 (10,59); 3,495 (10,9); 3,4784 (4,43); 3,3283 (1617,53); 2,8704 (7,94); 2,8534 (16); 2,8363 (7,21); 2,7109 (1,84); 2,6796 (1,87); 2,6752 (3,83); 2,6706 (5,21); 2,6661 (3,7); 2,6615 (1,75); 2,5409 (518,88); 2,524 (17,12); 2,5192 (25,92); 2,5106 (285,07); 2,5061 (570,05); 2,5015 (752,38); 2,4969 (542,38); 2,4924 (257,8); 2,3672 (1,77); 2,3375 (1,65); 2,3329 (3,54); 2,3283 (4,89); 2,3237 (3,5); 2,3192 (1,62); 2,2883 (0,4); 2,0743 (7,92); 1,2352 (0,6); 1,1469 (0,52); 0,008 (1,56); −0,0002 (42,99); −0,0086 (1,14)

No. Ib-66, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8,7858 (2,25); 8,7724 (4,17); 8,7588 (2,25); 8,2839 (9,88); 8,2781 (9,91); 7,7725 (6,59); 7,7662 (6,47); 7,752 (7,47); 7,7457 (7,3); 7,5306 (1,8); 7,5139 (3,83); 7,5092 (3,26); 7,4972 (2,4); 7,4927 (7,29); 7,4884 (2,54); 7,476 (3,39); 7,4716 (4,42); 7,4588 (12,42); 7,4383 (10,69); 7,1771 (1,33); 7,1739 (1,9); 7,1663 (11,98); 7,1555 (1,88); 7,1528 (2,46); 7,147 (14,39); 7,1369 (1,74); 7,1263 (9,98); 7,1185 (1,59); 3,5346 (4,43); 3,518 (11,27); 3,5032 (11,43); 3,4867 (4,88); 3,397 (0,48); 3,3308 (1140,9); 3,2844 (0,72); 3,2737 (0,57); 3,2547 (0,35); 2,9958 (0,58); 2,9811 (0,77); 2,9779 (0,63); 2,9638 (0,69); 2,8528 (8,19); 2,836 (16); 2,8193 (7,39); 2,7108 (0,38); 2,6798 (0,96); 2,6754 (2,06); 2,6708 (2,79); 2,6662 (1,99); 2,6616 (0,98); 2,5411 (103,07); 2,5242 (8,02); 2,5194 (12,49); 2,5108 (150,38); 2,5063 (305,14); 2,5017 (406,07); 2,4971 (294,04); 2,4926 (140,57); 2,3671 (0,41); 2,3375 (0,92); 2,3331 (1,92); 2,3285 (2,69); 2,3239 (1,93); 2,3193 (0,89); 2,1265 (0,74); 2,1235 (0,75); 2,0743 (3,08); 0,985 (0,82); 0,9671 (1,65); 0,9492 (0,75); −0,0002 (8,3)

No. Ib-67, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8,8337 (3,52); 8,8182 (6,62); 8,8032 (3,46); 8,6156 (13,41); 8,6105 (13,29); 8,3153 (2,45); 8,0624 (8,74); 8,0559 (8,57); 8,0414 (9,73); 8,035 (9,45); 7,6903 (14,73); 7,6694 (13,09); 7,5533 (2,6); 7,5487 (3,01); 7,54 (2,9); 7,5352 (6,09); 7,5323 (4,64); 7,5304 (4,97); 7,528 (4,47); 7,5209 (4,47); 7,5196 (4,48); 7,5171 (5,06); 7,5143 (6,71); 7,5095 (4,05); 7,5008 (3,34); 7,4962 (3,75); 7,4806 (5,18); 7,4761 (5,03); 7,4621 (9,85); 7,4576 (9,55); 7,443 (6,83); 7,4388 (5,58); 7,2942 (7,89); 7,2753 (16); 7,2699 (9,32); 7,2673 (8,23); 7,2585 (14,56); 7,2567 (14,13); 7,2489 (6,49); 7,2466 (6,51); 7,24 (7,34); 7,2375 (6,11); 5,7557 (10,13); 4,1288 (5,48); 4,113 (5,53); 4,0945 (12,26); 4,0785 (12); 4,06 (6,11); 4,0442 (5,86); 3,3248 (1190,69); 2,9433 (0,87); 2,6754 (4,56); 2,6708 (6,4); 2,6663 (4,66); 2,6618 (2,12); 2,5925 (0,37); 2,5242 (18,56); 2,5194 (29,27); 2,5108 (351,41); 2,5063 (715,6); 2,5018 (950,6); 2,4972 (690,72); 2,4927 (332,12); 2,3463 (0,38); 2,3377 (2,12); 2,3331 (4,58); 2,3285 (6,31); 2,3239 (4,59); 2,3196 (2,17); 2,0602 (0,54); 2,0407 (0,54); 1,9887 (0,44); 1,3357 (0,72); 1,2495 (0,96); 1,2354 (0,44); 1,1481 (0,65); −0,0002 (4,84)

No. Ib-68, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8,969 (1,7); 8,9534 (3,45); 8,9378 (1,74); 8,6458 (5,79); 8,6406 (5,82); 8,0957 (3,84); 8,0893 (3,78); 8,0747 (4,24); 8,0683 (4,19); 7,6981 (6,4); 7,6773 (5,78); 7,4815 (1,68); 7,4777 (2,72); 7,4616 (6,89); 7,4577 (8,42); 7,4515 (4,51); 7,4384 (5,67); 7,4341 (5,58); 7,4187 (2,44); 7,4142 (2,56); 7,4052 (0,34); 7,3985 (3,41); 7,3939 (3,09); 7,3798 (5,2); 7,3756 (5,2); 7,3624 (3,05); 7,3582 (2,82); 7,3076 (5,68); 7,3044 (5,33); 7,3035 (5,19); 7,2893 (4,2); 7,2851 (3,7); 5,7564 (16); 4,1402 (2,33); 4,1244 (2,37); 4,1058 (5,25); 4,0899 (5,14); 4,0712 (2,65); 4,0557 (2,74); 4,0393 (1,7); 4,0215 (1,67); 4,0037 (0,56); 3,331 (20,27); 2,5256 (0,45); 2,5208 (0,68); 2,5122 (9,03); 2,5077 (18,47); 2,5031 (24,58); 2,4986 (17,96); 2,4941 (8,72); 1,9902 (7,11); 1,3383 (0,35); 1,2502 (0,45); 1,1937 (1,94); 1,1759 (3,85); 1,1581 (1,89)

No. Ib-69, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8,9514 (2,59); 8,9359 (5,01); 8,9203 (2,52); 8,6573 (8,16); 8,652 (8,12); 8,1054 (5,02); 8,0991 (4,89); 8,0844 (5,51); 8,0781 (5,28); 7,7001 (8,53); 7,6792 (7,69); 7,6361 (6,74); 7,634 (6,74); 7,6164 (7,88); 7,6141 (7,62); 7,4426 (2,67); 7,4401 (2,82); 7,4241 (7,27); 7,4215 (7,1); 7,4056 (5,68); 7,4028 (5,2); 7,3727 (4,48); 7,3681 (5,23); 7,3533 (5,75); 7,3488 (6,25); 7,3342 (2,63); 7,3298 (2,47); 7,2738 (7,29); 7,2694 (6,91); 7,2552 (5,88); 7,2508 (5,35); 5,7565 (16); 4,1348 (3,13); 4,1191 (3,25); 4,1004 (6,83); 4,0847 (6,63); 4,0659 (3,51); 4,0502 (3,3); 4,0391 (1,09); 4,0212 (0,89); 3,33 (33,34); 2,5072 (28,26); 2,5028 (35,81); 2,4984 (26,54); 1,99 (3,54); 1,1935 (0,96); 1,1757 (1,86); 1,1579 (0,92); 0,0077 (0,44); −0,0002 (7,87); −0,008 (0,34)

No. Ib-70, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8,8969 (4,38); 8,8813 (8,71); 8,8657 (4,26); 8,6686 (13,99); 8,6633 (13,97); 8,1124 (9,29); 8,106 (9,08); 8,0914 (10,2); 8,085 (9,97); 7,8694 (13,07); 7,8674 (13,94); 7,8498 (14,07); 7,8476 (14,06); 7,6994 (15,35); 7,6785 (13,93); 7,4539 (6,71); 7,4512 (6,94); 7,4351 (14,5); 7,4324 (14,87); 7,4164 (9,23); 7,4136 (9); 7,2064 (11,15); 7,2026 (15,43); 7,1855 (15,65); 7,1836 (16); 7,1665 (13,3); 7,1623 (10,55); 7,1473 (7,61); 7,1432 (6,23); 5,7565 (15,75); 4,124 (5,3); 4,1082 (5,4); 4,0896 (11,97); 4,0738 (11,61); 4,0552 (6,19); 4,0388 (6,97); 4,0208 (1,65); 4,003 (0,54); 3,3288 (88,01); 2,6762 (0,43); 2,6715 (0,57); 2,667 (0,42); 2,525 (2,07); 2,5201 (3,23); 2,5116 (33,32); 2,5071 (66,4); 2,5025 (87,11); 2,4979 (62,89); 2,4934 (29,87); 2,3338 (0,4); 2,3292 (0,54); 2,3247 (0,4); 1,9897 (6,59); 1,3372 (0,74); 1,2498 (0,96); 1,2345 (0,33); 1,1932 (1,83); 1,1754 (3,67); 1,1576 (1,81); −0,0002 (2,39)

No. Ib-71, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

9,2461 (2,68); 9,2306 (5,36); 9,2149 (2,67); 8,6158 (9,19); 8,6104 (9,21); 8,0665 (6,24); 8,0601 (6,07); 8,0456 (6,92); 8,0391 (6,74); 7,7008 (10,46); 7,68 (9,37); 7,5481 (1,93); 7,5315 (4,04); 7,5269 (3,46); 7,5148 (2,58); 7,5103 (7,56); 7,5058 (2,6); 7,4936 (3,56); 7,4891 (4,43); 7,4725 (2,02); 7,1799 (1,5); 7,1768 (2,12); 7,1697 (12,91); 7,1502 (16); 7,1294 (10,62); 7,122 (1,82); 5,7571 (2,86); 4,1737 (3,76); 4,1579 (3,78); 4,1391 (8,52); 4,1233 (8,32); 4,1045 (4,27); 4,0887 (4,1); 3,3284 (45,35); 2,6721 (0,4); 2,5256 (1,16); 2,5207 (1,77); 2,5122 (21,98); 2,5076 (44,63); 2,503 (59,06); 2,4984 (42,43); 2,4939 (20,05); 2,3298 (0,38); 1,3375 (0,7); 1,2501 (0,89)

No. Ib-72, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

9,0228 (3,31); 9,0075 (6,42); 8,992 (3,26); 8,6489 (10,42); 8,6438 (10,34); 8,1 (6,18); 8,0938 (6,06); 8,079 (6,82); 8,0728 (6,54); 7,7725 (6,98); 7,753 (9,71); 7,7396 (3,47); 7,7211 (8,18); 7,7015 (16); 7,6804 (9,97); 7,665 (6,09); 7,6459 (7,34); 7,6269 (2,65); 7,4169 (8,41); 7,3983 (7,43); 5,7573 (5,45); 4,1488 (3,87); 4,133 (4,06); 4,1139 (8,42); 4,0982 (8,16); 4,0789 (4,34); 4,0632 (4,05); 4,039 (1,25); 4,0212 (1,19); 4,0034 (0,41); 3,331 (62,98); 2,6722 (0,4); 2,5073 (45,84); 2,503 (57,55); 2,4988 (43,55); 2,3297 (0,36); 1,9898 (4,83); 1,3379 (0,49); 1,2501 (0,58); 1,1934 (1,32); 1,1756 (2,54); 1,1578 (1,25); −0,0002 (11,89)

TABLE C

Compounds of formula (Ic)

(Ic)

embedded image

No.
X_n
R¹
R²
R³
R⁴
R⁵
R_m
cf.

Ic-1
2-F
H
H
H
H
H
2-CF₃
P8

3-F

cpd. 4

5-F

6-F

Ic-2
2-F
H
H
H
H
H
2-I
P8

3-F

cpd. 5

5-F

6-F

Ic-3
2-F
H
H
H
H
H
2-Br
P8

3-F

cpd. 6

5-F

6-F

Ic-4
2-F
H
H
H
H
H
2-Cl
P8

3-F

cpd. 7

5-F

6-F

Ic-5
2-Me
H
H
H
H
H
2-CF₃
P8

5-Cl

cpd. 1

Ic-6
2-Me
H
H
H
H
H
H
P8

5-Cl

cpd. 2

Ic-7
2-F
H
H
H
H
H
2-CF₃
P8

5-F

cpd. 3

Ic-8²
2-F
H
(CH₂)₄
H
H
2-CF₃
NMR

3-F

5-F

6-F

Ic-9
3-Cl
H
H
H
H
H
2-CF₃
P8

5-Cl

NMR

Ic-10
3-Cl
H
H
H
H
H
H
P8

5-Cl

NMR

Ic-11
3-Cl
H
H
H
H
H
3-Cl
P8

5-Cl

NMR

Ic-12
3-Cl
H
H
H
H
H
4-Cl
P8

5-Cl

NMR

Ic-13
3-Cl
H
H
H
H
H
3-Cl
P8

5-Cl

4-Cl
NMR

Ic-14
3-Cl
H
H
H
H
H
2-CF₃
P8

NMR

Ic-15
3-Cl
H
H
H
H
H
H
P8

NMR

Ic-16
3-Cl
H
H
H
H
H
4-Me
P8

5-Cl

NMR

Ic-17
3-Cl
H
H
H
H
H
2-F
P8

5-Cl

NMR

Ic-18
3-Cl
H
H
H
H
H
4-t-Bu
P8

5-Cl

NMR

Ic-19
3-Cl
H
H
H
H
H
3-OMe
P8

5-Cl

5-OMe
NMR

Ic-20
3-Cl
H
H
H
H
H
3-Br
P8

5-Cl

NMR

Ic-21
3-Cl
H
H
H
H
H
3-OMe
P8

5-Cl

NMR

Ic-22
3-Cl
H
H
H
H
H
2-OMe
P8

5-Cl

NMR

Ic-23
3-Cl
H
H
H
H
H
3-Me
P8

5-Cl

NMR

Ic-24
3-Cl
H
H
H
H
H
2-F
P8

5-Cl

5-Cl
NMR

Ic-25
3-Cl
H
H
H
H
H
2-F
P8

5-Cl

4-Cl
NMR

Ic-26
3-Cl
H
H
H
H
H
3-F
P8

5-Cl

4-F
NMR

Ic-27
3-Cl
H
H
H
H
H
2-Me
P8

5-Cl

NMR

Ic-28
3-Cl
H
H
H
H
H
2-Cl
P8

5-Cl

NMR

Ic-29
3-Cl
H
H
H
H
H
2-Cl
P8

5-Cl

4-F
NMR

Ic-30
3-Cl
H
H
H
H
H
4-CF₃
P8

5-Cl

NMR

Ic-31
3-Cl
H
H
H
H
H
3-CF₃
P8

5-Cl

NMR

Ic-32
3-Cl
H
H
H
H
H
2-Cl
P8

5-Cl

4-Cl
NMR

Ic-33
3-Cl
H
H
H
H
H
3-Cl
P8

5-Cl

5-Cl
NMR

Ic-34
3-Cl
H
H
H
H
H
3,4-OCH₂—O—
NMR

5-Cl

Ic-35
3-Cl
H
H
H
H
H
4-Et
P8

5-Cl

NMR

Ic-36
3-C1
H
H
H
H
H
2-F
P8

5-Cl

4-F
NMR

Ic-37
3-Cl
H
H
H
H
H
4-F
P8

5-Cl

NMR

Ic-38
3-Cl
H
H
H
H
H
4-NO₂
P8

5-Cl

NMR

Ic-39
3-Cl
H
H
H
H
H
3-F
P8

5-Cl

NMR

Ic-40
3-Cl
H
H
H
H
H
4-Br
P8

5-Cl

NMR

Ic-41
3-Cl
H
H
H
H
H
3-OMe
P8

5-Cl

4-OMe
NMR

Ic-42
3-Cl
H
H
H
H
H
2-F
P8

5-Cl

6-F
NMR

Ic-43
3-Cl
H
H
H
H
H
3-CN
P8

5-Cl

NMR

Ic-44
3-Cl
H
H
H
H
H
4-OMe
P8

NMR

Ic-45
3-Cl
H
H
H
H
H
4-NO₂
P8

NMR

Ic-46
3-Cl
H
H
H
H
H
4-Me
P8

NMR

Ic-47
3-Cl
H
H
H
H
H
4-OMe
P8

5-Cl

NMR

Ic-48
3-Cl
H
H
H
H
H
4-CN
P8

5-Cl

NMR

Ic-49
3-Cl
H
H
H
H
H
3-F
P8

5-Cl

5-F
NMR

Ic-50
2-OMe
H
H
H
H
H
4-F
P8

NMR

Ic-51
2-OMe
H
H
H
H
H
4-OMe
P8

NMR

Ic-52
2-OMe
H
H
H
H
H
3-Cl
P8

4-Cl
NMR

Ic-53
2-OMe
H
H
H
H
H
2-F
P8

NMR

Ic-54
2-OMe
H
H
H
H
H
4-t-Bu
P8

NMR

Ic-55
2-OMe
H
H
H
H
H
3-OMe
P8

5-OMe
NMR

Ic-56
2-OMe
H
H
H
H
H
3-CF₃
P8

NMR

Ic-57
2-OMe
H
H
H
H
H
3,4-OCH₂O—
P8

NMR

Ic-58
2-OMe
H
H
H
H
H
4-Et
P8

NMR

Ic-59
2-OMe
H
H
H
H
H
2-OMe
P8

NMR

Ic-60
2-OMe
H
H
H
H
H
4-CF₃
P8

NMR

Ic-61
2-OMe
H
H
H
H
H
3-Me
P8

NMR

Ic-62
2-OMe
H
H
H
H
H
2-F
P8

4-F
NMR

Ic-63
2-OMe
H
H
H
H
H
3-F
P8

5-F
NMR

Ic-64
2-OMe
H
H
H
H
H
2-F
P8

5-Cl
NMR

Ic-65
2-OMe
H
H
H
H
H
3-Br
P8

NMR

Ic-66
2-OMe
H
H
H
H
H
4-Br
P8

NMR

Ic-67
2-OMe
H
H
H
H
H
2-F
P8

6-F
NMR

Ic-68
2-OMe
H
H
H
H
H
3-CN
P8

NMR

Ic-69
2-OMe
H
H
H
H
H
2-Cl
P8

4-F
NMR

Ic-70
2-OMe
H
H
H
H
H
4-CN
P8

NMR

Ic-71
2-OMe
H
H
H
H
H
4-NO₂
P8

NMR

Ic-72
2-OMe
H
H
H
H
H
3-F
P8

NMR

Ic-73
2-OMe
H
H
H
H
H
3-F
P8

4-F
NMR

Ic-74
2-OMe
H
H
H
H
H
2-Cl
P8

NMR

Ic-75
2-OMe
H
H
H
H
H
3-Cl
P8

NMR

Ic-76
2-OMe
H
H
H
H
H
2-CF₃
P8

NMR

Ic-77
2-OMe
H
H
H
H
H
3-OMe
P8

4-OMe
NMR

Ic-78
2-Me
H
H
H
H
H
H
P8

Ic-79
2-Me
H
H
H
H
H
4-F
P8

NMR

Ic-80
2-Me
H
H
H
H
H
2-Cl
P8

NMR

Ic-81
2-Me
H
H
H
H
H
2-Cl
P8

4-Cl
NMR

Ic-82
2-Me
H
H
H
H
H
4-Cl
P8

NMR

Ic-83
2-Me
H
H
H
H
H
4-Me
P8

NMR

Ic-84
2-Me
H
H
H
H
H
2-F
P8

NMR

Ic-85
2-Me
H
H
H
H
H
4-t-Bu
P8

NMR

Ic-86
2-Me
H
H
H
H
H
3-F
P8

NMR

Ic-87
2-Me
H
H
H
H
H
3-CF₃
P8

NMR

Ic-88
2-Me
H
H
H
H
H
4-Et
P8

NMR

Ic-89
2-Me
H
H
H
H
H
2-OMe
P8

NMR

Ic-90
2-Me
H
H
H
H
H
4-CF₃
P8

NMR

Ic-91
2-Me
H
H
H
H
H
3-Cl
P8

NMR

Ic-92
2-Me
H
H
H
H
H
3-Cl
P8

5-Cl
NMR

Ic-93
2-Me
H
H
H
H
H
3-Me
P8

NMR

Ic-94
2-Me
H
H
H
H
H
2-F
P8

4-F
NMR

Ic-95
2-Me
H
H
H
H
H
3-F
P8

5-F
NMR

Ic-96
2-OMe
H
H
H
H
H
2-Cl
P8

4-Cl
NMR

Ic-97
2-OMe
H
H
H
H
H
4-Me
P8

NMR

Ic-98
2-OMe
H
H
H
H
H
2-Me
P8

NMR

Ic-99
2-OMe
H
H
H
H
H
3-Cl
P8

5-Cl
NMR

Ic-100
2-OMe
H
H
H
H
H
2-F
P8

4-Cl
NMR

Ic-101
2-Me
H
H
H
H
H
3,4-OCH₂O—
NMR

Ic-102
2-Me
H
H
H
H
H
4-OMe
NMR

Ic-103
2-Me
H
H
H
H
H
4-NO₂
NMR

Ic-104
2-Me
H
H
H
H
H
2-Me
P8

NMR

Ic-105
2-OMe
H
H
H
H
H
4-Cl
P8

NMR

Ic-106
2-OMe
H
H
H
H
H
H
P8

NMR

Ic-107
3-Cl
H
H
H
H
H
2-Cl
P8

NMR

Ic-108
2-Cl
H
H
H
H
H
2-CF₃
P8

NMR

Ic-109¹
2-F
H
(CH₂)₄
H
H
2-CF₃
NMR

3-F

5-F

6-F

¹cis-isomer

²trans-isomer

³pure enantiomer, absolute configuration not determined

No. Ic-8, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.5930 (4.34); 8.5707 (4.41); 7.7028 (8.47); 7.6835 (16.00); 7.6655 (4.47); 7.6110 (4.48); 7.5913 (5.42); 7.5730 (2.07); 7.2373 (6.21); 7.2186 (5.84); 5.3244 (0.33); 4.4056 (0.79); 4.3800 (1.82); 4.3569 (1.80); 4.3305 (0.63); 3.9048 (6.89); 3.3360 (479.87); 3.1736 (0.62); 3.1604 (0.68); 3.1489 (1.45); 3.1394 (1.64); 3.1192 (2.90); 3.1105 (2.96); 3.0903 (1.65); 3.0811 (1.51); 2.6756 (1.66); 2.6712 (2.34); 2.6667 (1.75); 2.5413 (0.95); 2.5245 (6.66); 2.5109 (134.72); 2.5066 (273.38); 2.5021 (365.93); 2.4976 (278.63); 2.4933 (145.18); 2.3994 (0.37); 2.3334 (1.82); 2.3289 (2.52); 2.3243 (1.93); 2.0254 (0.62); 2.0069 (1.36); 1.9871 (2.76); 1.9665 (2.96); 1.9321 (1.94); 1.8998 (3.15); 1.8817 (1.60); 1.8399 (4.69); 1.8093 (6.61); 1.7758 (3.24); 1.5172 (0.77); 1.4855 (3.06); 1.4571 (5.83); 1.4327 (3.35); 1.4074 (0.75); 1.3982 (0.77); 1.3501 (2.04); 1.3353 (1.26); 1.3157 (2.03); 1.2974 (2.27); 1.2881 (2.12); 1.2579 (2.77); 1.2350 (5.39); 0.8696 (0.63); 0.8537 (1.55); 0.8437 (2.14); 0.8297 (1.15); 0.1460 (0.61); 0.0080 (4.41); −0.0002 (143.78); −0.0084 (6.48); −0.1496 (0.61)

No. Ic-9, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.7437 (0.80); 8.7287 (1.51); 8.7138 (0.77); 8.6146 (16.00); 7.9526 (0.57); 7.8348 (0.41); 7.8014 (0.44); 7.7850 (2.05); 7.7657 (2.79); 7.7486 (1.15); 7.7304 (2.24); 7.7120 (1.56); 7.6618 (1.47); 7.6426 (1.92); 7.6235 (0.76); 7.5051 (2.18); 7.4861 (1.86); 3.5364 (1.18); 3.5202 (2.74); 3.5029 (2.78); 3.4866 (1.32); 3.3917 (0.38); 3.3412 (248.53); 3.1741 (2.47); 3.1559 (4.29); 3.1386 (2.16); 3.1252 (0.41); 2.8905 (3.70); 2.7303 (3.06); 2.6762 (0.67); 2.6717 (0.93); 2.6673 (0.68); 2.5573 (0.44); 2.5439 (0.90); 2.5251 (2.73); 2.5115 (51.58); 2.5072 (104.60); 2.5027 (139.39); 2.4981 (105.49); 2.4938 (54.29); 2.3338 (0.65); 2.3294 (0.92); 2.3250 (0.70); 1.2757 (2.27); 1.2592 (4.69); 1.2434 (2.97); 1.2272 (0.68); −0.0002 (4.60)

No. Ic-10, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.6707 (0.84); 8.6560 (1.61); 8.6414 (0.83); 8.5785 (16.00); 7.9562 (0.62); 7.9386 (0.67); 7.9351 (0.57); 7.7769 (4.33); 7.7644 (1.31); 7.7595 (5.10); 7.7557 (3.83); 7.6278 (0.35); 7.5298 (0.83); 7.5267 (0.69); 7.5235 (0.71); 7.5186 (0.78); 7.5117 (2.64); 7.5057 (1.32); 7.4970 (1.50); 7.4936 (2.32); 7.4901 (1.36); 7.4854 (0.55); 7.4641 (3.97); 7.4488 (2.80); 7.4452 (5.11); 7.4277 (2.04); 7.4247 (1.31); 7.0865 (0.38); 3.9048 (2.88); 3.5875 (1.26); 3.5712 (3.56); 3.5556 (3.77); 3.5394 (1.48); 3.4332 (0.35); 3.4199 (0.36); 3.4045 (0.47); 3.3452 (310.51); 3.3142 (0.85); 3.3054 (0.57); 3.1913 (2.57); 3.1747 (5.54); 3.1581 (2.33); 3.0945 (0.45); 2.6767 (0.49); 2.6721 (0.67); 2.6678 (0.52); 2.5425 (0.52); 2.5256 (2.19); 2.5119 (37.75); 2.5076 (75.85); 2.5031 (101.60); 2.4986 (77.57); 2.4943 (40.42); 2.3343 (0.47); 2.3299 (0.65); 2.3253 (0.49); 1.2556 (1.25); 1.2420 (0.57); 0.0080 (1.47); −0.0002 (45.73); −0.0084 (2.12)

No. Ic-11, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.8063 (0.83); 8.7917 (1.61); 8.7769 (0.81); 8.5860 (16.00); 7.8070 (2.28); 7.8026 (3.91); 7.7982 (2.60); 7.7484 (1.49); 7.7456 (2.09); 7.7420 (1.40); 7.7291 (1.79); 7.7262 (2.41); 7.7227 (1.61); 7.6090 (1.19); 7.6065 (1.41); 7.6039 (1.27); 7.6013 (1.19); 7.5890 (1.93); 7.5865 (1.98); 7.5839 (2.05); 7.5813 (1.67); 7.5175 (2.80); 7.4979 (4.03); 7.4783 (1.64); 3.9051 (3.31); 3.5847 (1.17); 3.5681 (3.41); 3.5526 (3.59); 3.5363 (1.39); 3.4329 (0.42); 3.3952 (0.51); 3.3789 (0.94); 3.3438 (293.68); 3.1874 (2.56); 3.1708 (5.25); 3.1614 (1.13); 3.1541 (2.20); 2.6767 (0.52); 2.6722 (0.74); 2.6678 (0.55); 2.5425 (0.73); 2.5255 (2.47); 2.5120 (42.26); 2.5077 (84.20); 2.5031 (111.68); 2.4986 (83.66); 2.4942 (42.26); 2.3344 (0.55); 2.3299 (0.76); 2.3253 (0.55); 0.0080 (0.91); −0.0002 (27.99); −0.0085 (1.11)

No. Ic-12, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.7565 (0.82); 8.7414 (1.62); 8.7271 (0.82); 8.5776 (16.00); 7.8035 (0.73); 7.7972 (5.79); 7.7924 (1.99); 7.7805 (2.09); 7.7757 (6.96); 7.7695 (0.95); 7.5502 (0.90); 7.5439 (6.93); 7.5391 (2.12); 7.5271 (1.91); 7.5224 (5.70); 7.5161 (0.75); 3.9050 (1.40); 3.5809 (1.11); 3.5645 (3.23); 3.5490 (3.39); 3.5329 (1.30); 3.3418 (270.48); 3.1828 (2.40); 3.1663 (4.89); 3.1496 (2.09); 2.6766 (0.50); 2.6720 (0.69); 2.6677 (0.52); 2.5424 (0.59); 2.5254 (2.28); 2.5118 (40.03); 2.5075 (79.52); 2.5030 (105.40); 2.4984 (79.26); 2.4941 (40.40); 2.3343 (0.51); 2.3297 (0.70); 2.3251 (0.53); 0.0080 (0.65); −0.0002 (19.46); −0.0084 (0.79)

No. Ic-13, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.8751 (0.80); 8.8604 (1.60); 8.8455 (0.78); 8.5862 (16.00); 7.9988 (4.31); 7.7783 (0.33); 7.7590 (10.22); 3.9052 (1.47); 3.5818 (1.05); 3.5654 (3.06); 3.5499 (3.21); 3.5336 (1.21); 3.3395 (192.38); 3.1835 (2.28); 3.1742 (1.35); 3.1670 (4.62); 3.1616 (1.59); 3.1502 (1.97); 2.6766 (0.48); 2.6721 (0.64); 2.6677 (0.49); 2.5254 (2.15); 2.5119 (37.34); 2.5076 (74.52); 2.5030 (98.82); 2.4985 (74.38); 2.4942 (37.75); 2.3343 (0.45); 2.3298 (0.64); 2.3252 (0.47); 0.0080 (1.65); −0.0002 (47.71); −0.0084 (1.91)

No. Ic-14, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.6647 (2.06); 8.6506 (3.86); 8.6368 (2.04); 8.5931 (16.00); 8.5044 (0.38); 8.4640 (10.04); 8.4517 (10.35); 8.3181 (0.64); 7.7765 (4.86); 7.7570 (6.43); 7.7324 (2.14); 7.7146 (5.42); 7.6961 (3.92); 7.6541 (3.85); 7.6351 (4.91); 7.6163 (1.80); 7.4531 (5.81); 7.4337 (13.16); 7.4212 (8.31); 4.1212 (0.51); 4.1079 (0.54); 3.9042 (7.57); 3.5770 (3.40); 3.5600 (8.74); 3.5450 (8.96); 3.5281 (3.81); 3.5074 (0.45); 3.4928 (0.41); 3.4753 (0.51); 3.4636 (0.52); 3.3496 (924.79); 3.1746 (1.88); 3.1615 (1.81); 2.9922 (6.46); 2.9751 (13.01); 2.9578 (5.78); 2.6769 (1.24); 2.6724 (1.71); 2.6679 (1.28); 2.5255 (6.45); 2.5120 (98.13); 2.5078 (193.12); 2.5033 (253.14); 2.4988 (190.30); 2.4946 (98.00); 2.3345 (1.15); 2.3300 (1.58); 2.3256 (1.16); 1.2340 (0.54); 0.0080 (1.62); −0.0002 (45.40); −0.0084 (2.00)

No. Ic-15, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.6193 (1.99); 8.6057 (3.70); 8.5915 (2.12); 8.5763 (16.00); 8.4281 (10.40); 8.4158 (10.70); 7.7918 (10.51); 7.7791 (3.12); 7.7743 (12.51); 7.7705 (9.25); 7.5360 (1.87); 7.5328 (1.24); 7.5243 (1.39); 7.5177 (6.36); 7.5121 (1.95); 7.5030 (3.39); 7.4997 (5.46); 7.4963 (2.94); 7.4689 (9.50); 7.4535 (6.81); 7.4498 (12.53); 7.4362 (2.00); 7.4323 (4.79); 7.4293 (2.96); 7.3925 (8.63); 7.3801 (8.38); 3.9046 (2.69); 3.5931 (3.60); 3.5761 (8.94); 3.5613 (9.14); 3.5444 (3.99); 3.5057 (0.69); 3.4727 (0.82); 3.3661 (1017.90); 3.2658 (0.81); 3.1752 (0.38); 3.1622 (0.41); 3.0236 (6.63); 3.0064 (13.35); 2.9892 (5.93); 2.6781 (0.86); 2.6736 (1.15); 2.6692 (0.86); 2.5267 (3.88); 2.5133 (64.82); 2.5090 (128.41); 2.5045 (170.09); 2.4999 (128.14); 2.4957 (64.96); 2.3357 (0.76); 2.3312 (1.07); 2.3268 (0.79); 1.3370 (0.93); 0.0080 (0.58); −0.0002 (17.36); −0.0084 (0.70)

No. Ic-16, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.5852 (1.08); 8.5710 (16.00); 8.5565 (0.84); 7.6836 (4.56); 7.6632 (5.03); 7.3119 (0.32); 7.2540 (4.18); 7.2341 (3.79); 3.9042 (6.08); 3.5694 (1.02); 3.5531 (2.93); 3.5375 (3.08); 3.5213 (1.17); 3.3887 (0.37); 3.3419 (195.96); 3.3075 (0.39); 3.1780 (2.20); 3.1615 (4.47); 3.1447 (2.00); 2.6766 (0.46); 2.6721 (0.65); 2.6676 (0.49); 2.5459 (0.40); 2.5423 (0.47); 2.5253 (2.13); 2.5118 (38.50); 2.5075 (77.27); 2.5030 (102.02); 2.4985 (76.68); 2.4941 (39.32); 2.4528 (0.39); 2.3708 (0.62); 2.3585 (0.37); 2.3383 (14.18); 2.3205 (0.72); 1.2748 (1.06); 1.2587 (2.17); 1.2434 (1.46); 1.2265 (0.35); −0.0002 (1.87)

No. Ic-17, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.5824 (16.00); 8.5035 (0.68); 8.4912 (1.14); 8.4745 (0.81); 7.5908 (0.90); 7.5865 (1.06); 7.5720 (1.76); 7.5678 (2.16); 7.5534 (0.95); 7.5492 (1.23); 7.5422 (0.68); 7.5377 (0.61); 7.5290 (0.67); 7.5241 (1.21); 7.5210 (1.04); 7.5101 (1.07); 7.5044 (1.26); 7.4984 (0.75); 7.4899 (0.78); 7.4852 (0.64); 7.2876 (1.87); 7.2833 (2.07); 7.2623 (4.60); 7.2430 (2.09); 3.9043 (4.72); 3.5792 (1.14); 3.5629 (3.33); 3.5471 (3.51); 3.5309 (1.35); 3.3857 (0.42); 3.3405 (201.36); 3.3041 (0.42); 3.1916 (2.54); 3.1750 (5.07); 3.1582 (2.20); 2.6765 (0.56); 2.6720 (0.76); 2.6675 (0.58); 2.5478 (0.38); 2.5422 (0.44); 2.5251 (2.43); 2.5116 (43.28); 2.5074 (86.53); 2.5029 (114.33); 2.4984 (86.20); 2.4941 (44.54); 2.3340 (0.50); 2.3297 (0.72); 2.3250 (0.52); 1.2558 (0.89); 1.2424 (0.39); −0.0002 (2.13)

No. Ic-18, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.5759 (4.09); 7.7112 (1.20); 7.6901 (1.44); 7.4659 (1.46); 7.4448 (1.23); 3.9043 (1.66); 3.5627 (0.72); 3.5471 (0.75); 3.3404 (62.88); 3.1826 (0.52); 3.1662 (1.10); 3.1496 (0.47); 2.5254 (0.64); 2.5118 (12.09); 2.5075 (24.49); 2.5030 (32.61); 2.4985 (24.74); 2.4944 (12.95); 1.3575 (0.33); 1.2999 (2.89); 1.2890 (16.00); 1.2585 (0.63); 1.2434 (0.44); −0.0002 (0.57)

No. Ic-19, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.6176 (0.64); 8.6035 (0.32); 8.5840 (5.48); 6.9277 (2.87); 6.9220 (2.99); 6.6303 (0.81); 6.6247 (1.45); 6.6190 (0.75); 3.9044 (1.28); 3.7852 (1.09); 3.7651 (16.00); 3.7540 (0.81); 3.5641 (0.35); 3.5474 (1.02); 3.5318 (1.07); 3.5157 (0.41); 3.3359 (43.29); 3.1785 (0.78); 3.1618 (1.59); 3.1450 (0.69); 2.5112 (16.86); 2.5071 (33.02); 2.5026 (43.23); 2.4981 (32.46); 2.4941 (16.67); 1.2581 (0.61); 1.2432 (0.42); 0.0080 (0.71); −0.0002 (20.22); −0.0084 (0.93)

No. Ic-20, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.8040 (0.82); 8.7895 (1.65); 8.7749 (0.86); 8.5854 (16.00); 8.3200 (0.35); 8.0339 (0.34); 7.9469 (2.27); 7.9425 (4.13); 7.9383 (2.77); 7.7854 (2.02); 7.7656 (2.27); 7.7353 (1.69); 7.7329 (1.67); 7.7306 (1.52); 7.7154 (1.87); 7.7129 (1.96); 7.4512 (2.51); 7.4315 (4.15); 7.4118 (1.94); 3.9045 (5.21); 3.5801 (1.17); 3.5636 (3.36); 3.5480 (3.50); 3.5319 (1.35); 3.3375 (180.73); 3.1852 (2.50); 3.1686 (5.03); 3.1519 (2.20); 2.6762 (0.68); 2.6719 (0.96); 2.6675 (0.72); 2.5420 (0.49); 2.5249 (3.02); 2.5073 (111.61); 2.5028 (148.09); 2.4983 (112.69); 2.3339 (0.75); 2.3296 (1.01); 2.3252 (0.77); 1.2553 (1.25); 1.2351 (0.80); 1.2098 (0.75); 1.1937 (0.62); 0.0079 (1.42); −0.0002 (43.13); −0.0084 (1.96)

No. Ic-21, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.6590 (0.53); 8.6439 (1.02); 8.6293 (0.52); 8.5814 (10.01); 7.3801 (0.43); 7.3612 (1.98); 7.3545 (1.43); 7.3512 (1.69); 7.3449 (3.80); 7.3360 (0.40); 7.3323 (0.48); 7.3178 (1.51); 7.3104 (1.83); 7.0860 (0.80); 7.0789 (1.19); 7.0717 (1.06); 7.0633 (1.25); 7.0565 (0.68); 3.9045 (2.70); 3.7840 (16.00); 3.7713 (0.76); 3.5774 (0.69); 3.5606 (2.00); 3.5450 (2.10); 3.5288 (0.79); 3.3369 (64.12); 3.1857 (1.50); 3.1692 (3.05); 3.1616 (0.77); 3.1523 (1.28); 2.6762 (0.40); 2.6719 (0.55); 2.6676 (0.41); 2.5251 (1.88); 2.5116 (31.24); 2.5073 (62.40); 2.5028 (82.51); 2.4983 (62.20); 2.4940 (31.96); 2.3341 (0.38); 2.3295 (0.53); 2.3250 (0.40); 1.2554 (0.48); 0.0080 (1.12); −0.0002 (33.46); −0.0082 (1.48)

No. Ic-22, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.5762 (10.82); 8.3193 (0.33); 8.3082 (0.60); 8.2935 (1.16); 8.2792 (0.59); 7.6841 (1.40); 7.6797 (1.55); 7.6650 (1.51); 7.6606 (1.59); 7.4666 (0.78); 7.4621 (0.80); 7.4443 (1.42); 7.4275 (0.93); 7.4229 (0.89); 7.1108 (2.30); 7.0900 (1.99); 7.0196 (1.26); 7.0009 (2.19); 6.9822 (1.07); 3.9043 (3.36); 3.8071 (16.00); 3.7650 (0.45); 3.6117 (0.95); 3.5954 (2.72); 3.5795 (2.84); 3.5634 (1.09); 3.3783 (0.65); 3.3428 (209.28); 3.1923 (1.91); 3.1757 (3.84); 3.1590 (1.71); 2.6758 (0.44); 2.6719 (0.58); 2.6680 (0.46); 2.5421 (0.44); 2.5072 (67.19); 2.5029 (89.05); 2.4986 (69.26); 2.3295 (0.54); 2.3254 (0.41); 1.2732 (0.34); 1.2561 (0.93); 1.2422 (0.54); −0.0002 (1.27)

No. Ic-23, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.6215 (0.80); 8.6070 (1.50); 8.5918 (0.94); 8.5774 (15.20); 7.5947 (2.95); 7.5685 (0.85); 7.5647 (0.81); 7.5589 (1.36); 7.5562 (1.41); 7.5468 (1.18); 7.3479 (0.42); 7.3288 (3.60); 7.3176 (4.45); 7.3152 (4.42); 3.9044 (4.62); 3.5708 (1.04); 3.5542 (3.00); 3.5386 (3.12); 3.5223 (1.20); 3.3939 (0.33); 3.3423 (251.84); 3.1835 (2.25); 3.1742 (1.04); 3.1669 (4.56); 3.1500 (1.97); 2.6767 (0.50); 2.6721 (0.68); 2.6675 (0.50); 2.5424 (0.33); 2.5255 (1.94); 2.5120 (40.67); 2.5076 (82.25); 2.5031 (109.10); 2.4986 (82.16); 2.4942 (42.20); 2.3640 (0.94); 2.3399 (16.00); 2.3254 (1.23); 1.2742 (0.96); 1.2579 (2.11); 1.2431 (1.51); 1.2253 (0.38); −0.0002 (1.21)

No. Ic-24, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.6528 (0.77); 8.6394 (1.34); 8.6248 (1.03); 8.6041 (0.34); 8.5904 (16.00); 8.3191 (0.34); 7.6119 (0.92); 7.6049 (1.38); 7.6011 (1.13); 7.5941 (1.46); 7.5904 (0.93); 7.5833 (2.03); 7.5773 (2.87); 7.5721 (2.39); 7.5623 (2.36); 7.5556 (1.36); 7.3765 (2.27); 7.3523 (2.61); 7.3300 (1.69); 3.9044 (6.00); 3.5711 (1.17); 3.5546 (3.31); 3.5389 (3.49); 3.5227 (1.37); 3.3406 (241.25); 3.1858 (2.45); 3.1693 (4.94); 3.1617 (1.22); 3.1524 (2.08); 2.6766 (0.69); 2.6721 (0.94); 2.6676 (0.71); 2.5253 (3.24); 2.5118 (54.48); 2.5076 (108.08); 2.5030 (142.51); 2.4985 (107.50); 2.4943 (55.39); 2.3343 (0.64); 2.3298 (0.90); 2.3253 (0.65); 1.2554 (0.88); 1.2346 (0.39); 1.2107 (0.78); 1.1944 (0.75); −0.0002 (2.26)

No. Ic-25, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.5812 (16.00); 8.5585 (1.18); 8.5456 (0.64); 7.6127 (1.69); 7.5923 (3.36); 7.5721 (2.12); 7.5546 (2.00); 7.5497 (2.11); 7.5287 (1.97); 7.5238 (2.07); 7.3869 (2.03); 7.3823 (2.04); 7.3660 (1.68); 7.3614 (1.71); 3.9044 (4.83); 3.5738 (1.00); 3.5576 (2.95); 3.5419 (3.11); 3.5258 (1.19); 3.3843 (0.38); 3.3746 (0.80); 3.3416 (244.93); 3.3032 (0.35); 3.1843 (2.27); 3.1678 (4.57); 3.1511 (1.97); 2.6767 (0.57); 2.6722 (0.78); 2.6676 (0.59); 2.5476 (0.43); 2.5254 (2.46); 2.5120 (44.34); 2.5076 (89.18); 2.5031 (117.74); 2.4985 (87.67); 2.4941 (44.10); 2.3345 (0.54); 2.3298 (0.74); 2.3252 (0.57); 1.2730 (0.37); 1.2558 (1.01); 1.2426 (0.62); 1.2106 (0.45); 1.1944 (0.43); −0.0002 (2.22)

No. Ic-26, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.7944 (0.91); 8.7800 (1.77); 8.7656 (0.90); 8.5845 (16.00); 7.8306 (0.97); 7.8256 (1.05); 7.8112 (1.04); 7.8058 (1.19); 7.8019 (1.17); 7.7966 (1.10); 7.7821 (0.96); 7.7770 (1.01); 7.6827 (0.79); 7.6724 (0.86); 7.6657 (1.09); 7.6615 (1.17); 7.6553 (1.09); 7.6509 (1.12); 7.5847 (1.18); 7.5640 (1.73); 7.5587 (1.35); 7.5428 (1.03); 7.5378 (1.74); 7.5168 (0.81); 3.9044 (2.95); 3.5804 (1.24); 3.5640 (3.60); 3.5484 (3.79); 3.5321 (1.46); 3.3395 (193.72); 3.1820 (2.65); 3.1748 (1.08); 3.1655 (5.35); 3.1487 (2.30); 2.6764 (0.54); 2.6721 (0.72); 2.6680 (0.56); 2.5074 (82.52); 2.5031 (108.08); 2.4988 (82.86); 2.3341 (0.51); 2.3296 (0.71); 2.3257 (0.54); 0.0075 (1.01); −0.0002 (28.08); −0.0081 (1.49)

No. Ic-27, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.5935 (14.26); 8.4246 (0.71); 8.4096 (1.38); 8.3949 (0.71); 7.3272 (0.66); 7.3236 (0.78); 7.3107 (0.92); 7.3055 (2.19); 7.2916 (2.45); 7.2871 (2.09); 7.2751 (2.54); 7.2252 (4.55); 7.2069 (3.86); 7.1889 (0.71); 3.9042 (2.75); 3.5685 (1.06); 3.5521 (3.18); 3.5362 (3.35); 3.5200 (1.27); 3.3390 (158.79); 3.3073 (0.37); 3.1764 (2.41); 3.1600 (4.88); 3.1431 (2.00); 2.6758 (0.42); 2.6717 (0.58); 2.6671 (0.43); 2.5246 (2.01); 2.5111 (34.25); 2.5070 (66.90); 2.5025 (87.56); 2.4980 (65.83); 2.4938 (33.96); 2.3338 (0.44); 2.3292 (0.58); 2.3248 (0.43); 2.2733 (16.00); 0.0078 (0.68); −0.0002 (17.89); −0.0082 (0.81)

No. Ic-28, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.6411 (0.86); 8.6262 (1.66); 8.6115 (1.05); 8.5979 (16.00); 7.4913 (1.72); 7.4719 (3.91); 7.4539 (1.30); 7.4428 (2.67); 7.4316 (2.34); 7.4232 (1.45); 7.4119 (1.75); 7.4031 (0.66); 7.3906 (7.16); 7.3811 (4.36); 3.9044 (2.81); 3.5578 (1.24); 3.5409 (3.58); 3.5251 (3.73); 3.5085 (1.49); 3.3388 (157.84); 3.3155 (0.62); 3.1827 (2.73); 3.1740 (1.19); 3.1657 (5.35); 3.1485 (2.27); 2.6763 (0.55); 2.6720 (0.75); 2.6674 (0.58); 2.5249 (2.85); 2.5114 (42.86); 2.5072 (83.76); 2.5028 (109.60); 2.4983 (83.23); 2.3339 (0.51); 2.3295 (0.69); 2.3251 (0.52); 0.0079 (1.26); −0.0002 (33.16); −0.0082 (1.44)

No. Ic-29, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.6662 (0.80); 8.6514 (1.59); 8.6366 (0.82); 8.5960 (16.00); 7.5098 (2.08); 7.5035 (2.18); 7.4872 (2.14); 7.4809 (2.20); 7.4751 (1.93); 7.4595 (1.91); 7.4536 (2.39); 7.4381 (2.21); 7.3122 (1.34); 7.3058 (1.26); 7.2909 (2.35); 7.2845 (2.17); 7.2696 (1.08); 7.2633 (1.00); 3.9043 (4.34); 3.5521 (1.10); 3.5352 (3.17); 3.5194 (3.35); 3.5028 (1.33); 3.3939 (0.33); 3.3426 (250.44); 3.1772 (2.43); 3.1607 (5.37); 3.1433 (2.01); 2.6765 (0.47); 2.6720 (0.66); 2.6674 (0.51); 2.5251 (2.14); 2.5117 (37.29); 2.5074 (75.08); 2.5029 (99.83); 2.4983 (75.63); 2.4940 (39.21); 2.3341 (0.46); 2.3296 (0.63); 2.3252 (0.48); −0.0002 (1.50)

No. Ic-30, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.9154 (0.87); 8.9009 (1.73); 8.8860 (0.85); 8.5823 (16.00); 7.9748 (3.43); 7.9544 (4.87); 7.8592 (5.21); 7.8385 (3.70); 3.9047 (4.08); 3.6134 (1.09); 3.5972 (3.23); 3.5815 (3.40); 3.5656 (1.32); 3.3826 (0.36); 3.3408 (222.36); 3.3049 (0.38); 3.2042 (2.37); 3.1879 (4.70); 3.1714 (2.20); 3.1623 (0.61); 2.6770 (0.48); 2.6725 (0.69); 2.6682 (0.52); 2.5425 (0.39); 2.5257 (2.21); 2.5120 (40.38); 2.5079 (80.10); 2.5034 (105.92); 2.4990 (80.58); 2.3345 (0.51); 2.3302 (0.70); 2.3257 (0.54); −0.0002 (1.87)

No. Ic-31, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.9518 (0.79); 8.9372 (1.56); 8.9223 (0.79); 8.5871 (16.00); 8.1095 (3.03); 8.0899 (1.73); 8.0700 (1.86); 7.9125 (1.48); 7.8931 (1.81); 7.7382 (1.44); 7.7186 (2.43); 7.6992 (1.08); 3.9046 (4.64); 3.6115 (1.07); 3.5950 (3.14); 3.5796 (3.28); 3.5634 (1.25); 3.3413 (256.61); 3.2061 (2.34); 3.1894 (4.74); 3.1726 (2.13); 2.6769 (0.55); 2.6724 (0.73); 2.6678 (0.55); 2.5427 (0.55); 2.5256 (2.30); 2.5120 (42.41); 2.5078 (84.93); 2.5033 (112.19); 2.4988 (84.37); 2.4945 (43.36); 2.3346 (0.53); 2.3300 (0.73); 2.3256 (0.55); −0.0002 (2.12)

No. Ic-32, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.7082 (0.81); 8.6932 (1.63); 8.6787 (0.80); 8.5956 (16.00); 7.6775 (4.12); 7.6726 (4.32); 7.5115 (2.03); 7.5065 (1.89); 7.4909 (3.13); 7.4859 (3.09); 7.4225 (5.09); 7.4019 (3.26); 3.9042 (3.92); 3.5542 (1.08); 3.5374 (3.08); 3.5216 (3.22); 3.5050 (1.28); 3.3401 (184.88); 3.1762 (2.34); 3.1594 (4.63); 3.1422 (1.96); 2.6763 (0.44); 2.6719 (0.62); 2.6673 (0.47); 2.5251 (2.05); 2.5115 (35.63); 2.5073 (70.89); 2.5028 (93.25); 2.4983 (70.15); 2.4941 (36.03); 2.3339 (0.42); 2.3296 (0.58); 2.3251 (0.44); −0.0002 (1.86)

No. Ic-33, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.9156 (0.87); 8.9007 (1.74); 8.8863 (0.88); 8.5925 (16.00); 7.8156 (1.68); 7.8108 (3.93); 7.8063 (3.58); 7.7894 (11.38); 7.7847 (8.20); 3.9044 (3.67); 3.5792 (1.10); 3.5627 (3.25); 3.5471 (3.44); 3.5309 (1.33); 3.3392 (225.17); 3.3129 (0.82); 3.1834 (2.45); 3.1745 (1.50); 3.1669 (4.95); 3.1500 (2.13); 2.6765 (0.57); 2.6723 (0.79); 2.6677 (0.62); 2.5252 (2.49); 2.5076 (90.58); 2.5031 (120.42); 2.4987 (92.44); 2.3344 (0.58); 2.3299 (0.80); 2.3254 (0.60); 0.0079 (1.32); −0.0002 (38.37); −0.0083 (1.95)

No. Ic-34, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.5764 (14.66); 8.5109 (0.79); 8.4964 (1.58); 8.4817 (0.77); 7.3753 (1.96); 7.3710 (2.21); 7.3549 (2.13); 7.3506 (2.47); 7.2957 (4.10); 7.2917 (3.79); 6.9784 (4.09); 6.9581 (3.71); 6.1553 (0.58); 6.0853 (16.00); 3.9045 (4.23); 3.5511 (0.97); 3.5346 (2.85); 3.5191 (2.99); 3.5031 (1.19); 3.3401 (210.82); 3.1739 (0.58); 3.1646 (2.22); 3.1481 (4.33); 3.1314 (1.86); 2.6766 (0.53); 2.6721 (0.73); 2.6677 (0.56); 2.5421 (0.48); 2.5254 (2.33); 2.5118 (42.24); 2.5075 (85.09); 2.5030 (113.06); 2.4985 (86.09); 2.4945 (45.17); 2.3343 (0.53); 2.3298 (0.74); 2.3253 (0.58); 1.2735 (0.81); 1.2564 (1.78); 1.2427 (1.23); 0.0080 (1.00); −0.0002 (31.22); −0.0084 (1.43)

No. Ic-35, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.5860 (1.06); 8.5736 (16.00); 8.5589 (0.92); 7.7037 (4.79); 7.6832 (5.31); 7.2858 (4.84); 7.2653 (4.39); 3.9044 (3.42); 3.5740 (1.05); 3.5575 (2.96); 3.5419 (3.09); 3.5259 (1.20); 3.3402 (209.32); 3.1808 (2.20); 3.1743 (1.02); 3.1642 (4.51); 3.1476 (2.03); 3.1372 (0.46); 2.6766 (0.75); 2.6675 (1.88); 2.6485 (3.90); 2.6295 (4.02); 2.6107 (1.45); 2.5422 (0.47); 2.5253 (2.44); 2.5119 (44.58); 2.5076 (88.21); 2.5030 (115.94); 2.4986 (87.01); 2.4943 (44.94); 2.3343 (0.56); 2.3297 (0.76); 2.3253 (0.57); 1.2760 (1.95); 1.2596 (4.04); 1.2441 (2.72); 1.2275 (0.71); 1.2054 (5.89); 1.1864 (12.34); 1.1674 (5.70); 0.0079 (0.93); −0.0002 (27.20); −0.0083 (1.23)

No. Ic-36, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.6175 (0.33); 8.5816 (16.00); 8.5159 (0.69); 8.5003 (1.37); 8.4885 (0.62); 8.3196 (0.37); 7.6769 (0.89); 7.6601 (1.05); 7.6555 (1.81); 7.6387 (1.80); 7.6344 (1.14); 7.6174 (0.91); 7.3650 (1.00); 7.3589 (1.07); 7.3413 (1.14); 7.3358 (1.44); 7.3318 (1.21); 7.3143 (0.96); 7.3081 (0.98); 7.1903 (0.88); 7.1844 (0.83); 7.1697 (1.56); 7.1638 (1.49); 7.1480 (0.77); 7.1422 (0.72); 3.9045 (5.11); 3.6215 (0.33); 3.6119 (0.36); 3.5726 (1.12); 3.5564 (3.17); 3.5406 (3.33); 3.5246 (1.31); 3.3454 (336.90); 3.1853 (2.36); 3.1687 (5.34); 3.1524 (2.20); 3.1363 (0.41); 3.1257 (0.36); 2.7314 (0.54); 2.6768 (0.60); 2.6722 (0.84); 2.6678 (0.64); 2.5256 (2.58); 2.5120 (47.71); 2.5077 (96.72); 2.5032 (128.99); 2.4987 (97.66); 2.4945 (50.67); 2.3344 (0.59); 2.3299 (0.82); 2.3254 (0.62); 1.2760 (2.48); 1.2596 (5.12); 1.2437 (3.22); 1.2275 (0.74); −0.0002 (1.33)

No. Ic-37, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.6998 (0.77); 8.6852 (1.52); 8.6704 (0.78); 8.5906 (0.51); 8.5784 (16.00); 7.8634 (0.35); 7.8559 (2.76); 7.8505 (1.19); 7.8420 (3.04); 7.8337 (3.27); 7.8253 (1.21); 7.8199 (2.96); 7.8127 (0.36); 7.3159 (0.40); 7.3086 (3.11); 7.3034 (1.08); 7.2914 (1.22); 7.2863 (5.94); 7.2812 (1.27); 7.2692 (0.98); 7.2641 (2.92); 7.2567 (0.38); 3.9045 (4.49); 3.5790 (1.06); 3.5625 (3.13); 3.5469 (3.31); 3.5307 (1.28); 3.3960 (0.35); 3.3431 (259.36); 3.1832 (2.33); 3.1746 (1.15); 3.1667 (4.72); 3.1499 (2.03); 2.6769 (0.48); 2.6723 (0.67); 2.6678 (0.48); 2.5257 (1.86); 2.5122 (37.92); 2.5078 (77.47); 2.5033 (103.55); 2.4987 (78.35); 2.4943 (40.51); 2.3345 (0.51); 2.3301 (0.69); 2.3254 (0.52); 1.2555 (0.83); −0.0002 (1.46)

No. Ic-38, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

9.0167 (0.81); 9.0022 (1.59); 8.9876 (0.80); 8.5845 (16.00); 8.3374 (2.43); 8.3322 (1.54); 8.3258 (5.86); 8.3207 (2.88); 8.3153 (3.36); 8.3086 (2.36); 8.3036 (6.52); 8.2978 (0.91); 8.1868 (0.49); 8.1813 (3.04); 8.1763 (0.94); 8.1639 (0.82); 8.1591 (2.26); 8.0166 (0.93); 8.0109 (6.25); 8.0060 (2.00); 7.9934 (1.83); 7.9887 (5.44); 7.9829 (0.71); 3.9046 (6.52); 3.6197 (1.07); 3.6037 (3.08); 3.5880 (3.22); 3.5722 (1.27); 3.3421 (162.07); 3.2088 (2.27); 3.1923 (4.46); 3.1756 (2.10); 2.6770 (0.65); 2.6725 (0.89); 2.6681 (0.66); 2.5426 (0.68); 2.5257 (2.90); 2.5122 (51.70); 2.5079 (102.36); 2.5034 (134.23); 2.4989 (100.05); 2.4946 (50.87); 2.3346 (0.63); 2.3301 (0.87); 2.3257 (0.64); 1.2556 (0.81); −0.0002 (2.35)

No. Ic-39, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.7833 (0.74); 8.7687 (1.49); 8.7545 (0.77); 8.5839 (16.00); 8.3207 (0.36); 7.6850 (0.34); 7.6662 (0.39); 7.6373 (1.74); 7.6179 (2.44); 7.5725 (1.09); 7.5663 (1.40); 7.5627 (1.15); 7.5473 (1.35); 7.5404 (2.26); 7.5252 (1.33); 7.5196 (2.00); 7.5050 (1.79); 7.5002 (1.14); 7.4854 (0.98); 7.3950 (0.92); 7.3903 (0.82); 7.3885 (0.84); 7.3743 (1.48); 7.3680 (1.45); 7.3523 (0.84); 7.3480 (0.79); 3.9045 (6.60); 3.5879 (1.11); 3.5715 (3.26); 3.5558 (3.42); 3.5397 (1.34); 3.3424 (105.00); 3.1892 (2.47); 3.1727 (5.10); 3.1559 (2.16); 2.9443 (0.36); 2.6766 (0.61); 2.6722 (0.85); 2.6676 (0.64); 2.5424 (0.72); 2.5255 (2.79); 2.5119 (46.96); 2.5076 (94.04); 2.5031 (124.49); 2.4986 (93.39); 2.4943 (47.55); 2.3343 (0.59); 2.3299 (0.81); 2.3254 (0.60); 1.2554 (0.97); −0.0002 (1.91)

No. Ic-40, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.7615 (0.77); 8.7466 (1.55); 8.7317 (0.78); 8.5909 (0.59); 8.5852 (0.49); 8.5756 (16.00); 8.3197 (0.40); 7.8244 (0.60); 7.8037 (0.76); 7.7265 (2.86); 7.7214 (1.32); 7.7100 (1.86); 7.7047 (8.36); 7.6805 (8.72); 7.6752 (2.07); 7.6639 (1.29); 7.6587 (3.15); 7.6051 (0.33); 3.9045 (5.78); 3.5777 (1.05); 3.5613 (2.97); 3.5457 (3.15); 3.5296 (1.25); 3.3424 (176.27); 3.1811 (2.23); 3.1645 (4.44); 3.1479 (1.91); 2.6766 (0.67); 2.6722 (0.93); 2.6676 (0.70); 2.5425 (0.70); 2.5254 (2.92); 2.5119 (53.03); 2.5076 (106.07); 2.5031 (139.97); 2.4986 (105.34); 2.4942 (53.97); 2.3343 (0.66); 2.3299 (0.91); 2.3253 (0.69); 1.2554 (0.85); 0.0080 (0.68); −0.0002 (20.52); −0.0085 (0.86)

No. Ic-41, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.5903 (0.36); 8.5796 (11.35); 8.5407 (0.62); 8.5263 (1.23); 8.5115 (0.62); 7.4078 (1.21); 7.4028 (1.56); 7.3870 (1.17); 7.3821 (2.11); 7.3730 (3.29); 7.3683 (2.16); 7.0100 (2.66); 6.9892 (2.39); 3.9044 (3.14); 3.7960 (15.86); 3.7783 (16.00); 3.5628 (0.76); 3.5463 (2.08); 3.5308 (2.21); 3.5144 (0.92); 3.3978 (0.33); 3.3429 (198.92); 3.1794 (1.63); 3.1746 (1.46); 3.1620 (3.68); 3.1457 (1.36); 2.6767 (0.47); 2.6723 (0.62); 2.6678 (0.45); 2.5422 (0.50); 2.5253 (2.21); 2.5118 (36.52); 2.5076 (70.76); 2.5031 (91.77); 2.4986 (68.50); 2.4944 (35.01); 2.3344 (0.43); 2.3299 (0.57); 2.3255 (0.41); 1.2554 (0.40); 0.0080 (0.45); −0.0002 (11.83); −0.0084 (0.51)

No. Ic-42, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.9141 (0.81); 8.8991 (1.53); 8.8844 (0.80); 8.6404 (0.35); 8.6201 (0.37); 8.5902 (16.00); 7.5411 (0.53); 7.5245 (1.06); 7.5201 (1.02); 7.5077 (0.76); 7.5034 (2.00); 7.4868 (1.01); 7.4823 (1.17); 7.4658 (0.53); 7.1799 (0.76); 7.1728 (3.51); 7.1530 (4.87); 7.1325 (2.84); 7.1252 (0.57); 3.9043 (3.66); 3.5705 (1.25); 3.5535 (3.33); 3.5372 (3.45); 3.5205 (1.49); 3.3433 (216.18); 3.1660 (2.75); 3.1486 (5.00); 3.1311 (2.25); 2.6766 (0.66); 2.6721 (0.89); 2.6677 (0.68); 2.5253 (2.96); 2.5117 (51.72); 2.5075 (102.01); 2.5030 (134.03); 2.4986 (101.33); 2.3342 (0.60); 2.3298 (0.84); 2.3253 (0.64); 1.2552 (0.92); 0.0079 (0.91); −0.0002 (26.73); −0.0084 (1.26)

No. Ic-43, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.9105 (0.77); 8.8961 (1.48); 8.8818 (0.74); 8.5891 (16.00); 8.3199 (0.34); 8.1822 (2.25); 8.1784 (3.83); 8.1751 (2.49); 8.1012 (1.29); 8.0982 (1.80); 8.0941 (1.29); 8.0814 (1.43); 8.0781 (1.90); 8.0743 (1.40); 8.0176 (1.33); 8.0144 (1.90); 8.0110 (1.27); 7.9983 (1.55); 7.9947 (2.14); 7.9917 (1.37); 7.7140 (1.95); 7.6945 (3.39); 7.6748 (1.58); 3.9045 (5.38); 3.6015 (1.05); 3.5849 (2.99); 3.5693 (3.13); 3.5531 (1.23); 3.3445 (238.06); 3.1971 (2.21); 3.1805 (4.53); 3.1635 (2.03); 2.9446 (1.61); 2.7843 (1.20); 2.6770 (0.57); 2.6726 (0.79); 2.6680 (0.58); 2.5429 (0.69); 2.5258 (2.40); 2.5124 (44.63); 2.5080 (90.29); 2.5034 (119.98); 2.4989 (90.10); 2.4945 (45.78); 2.3348 (0.55); 2.3301 (0.77); 2.3257 (0.57); 1.9581 (1.26); 1.2555 (0.76); −0.0002 (1.11)

No. Ic-44, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.5718 (3.99); 8.4684 (0.51); 8.4544 (0.98); 8.4406 (0.52); 8.4213 (2.59); 8.4090 (2.64); 7.7874 (0.40); 7.7803 (3.50); 7.7753 (1.18); 7.7631 (1.12); 7.7581 (3.76); 7.7510 (0.44); 7.3753 (2.03); 7.3630 (1.99); 6.9976 (0.44); 6.9904 (3.77); 6.9854 (1.22); 6.9731 (1.13); 6.9682 (3.58); 6.9610 (0.43); 3.9045 (2.37); 3.8238 (0.81); 3.7982 (16.00); 3.5660 (0.73); 3.5490 (1.89); 3.5342 (1.91); 3.5173 (0.82); 3.3433 (137.20); 3.0064 (1.47); 2.9893 (2.94); 2.9719 (1.32); 2.6723 (0.39); 2.5255 (1.23); 2.5121 (21.43); 2.5077 (43.36); 2.5032 (57.55); 2.4987 (43.22); 2.4943 (22.12); 2.3298 (0.36); −0.0002 (0.83)

No. Ic-45, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.9584 (1.98); 8.9446 (3.84); 8.9304 (2.03); 8.5796 (15.49); 8.4326 (9.56); 8.4203 (9.94); 8.3307 (1.68); 8.3249 (13.18); 8.3200 (5.35); 8.3075 (4.77); 8.3027 (16.00); 8.2970 (2.52); 8.0294 (2.12); 8.0237 (15.10); 8.0190 (5.42); 8.0062 (4.49); 8.0016 (13.68); 7.9959 (2.12); 7.4043 (8.18); 7.3920 (8.03); 3.9046 (8.63); 3.6230 (2.95); 3.6061 (7.98); 3.5912 (8.11); 3.5746 (3.33); 3.3422 (470.77); 3.0396 (5.97); 3.0226 (12.10); 3.0055 (5.41); 2.6767 (1.07); 2.6723 (1.49); 2.6679 (1.15); 2.5252 (5.40); 2.5076 (169.60); 2.5032 (224.06); 2.4987 (170.80); 2.3344 (1.03); 2.3299 (1.44); 2.3256 (1.09); 1.3377 (0.53); −0.0002 (3.69)

No. Ic-46, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.5714 (6.74); 8.5331 (0.83); 8.5192 (1.57); 8.5055 (0.81); 8.4207 (4.23); 8.4085 (4.36); 7.7022 (5.18); 7.6818 (5.75); 7.3767 (3.47); 7.3644 (3.36); 7.2595 (4.66); 7.2396 (4.26); 3.9045 (3.35); 3.5741 (1.28); 3.5571 (3.31); 3.5422 (3.37); 3.5253 (1.41); 3.3762 (0.32); 3.3409 (155.21); 3.1746 (0.45); 3.1615 (0.46); 3.0112 (2.57); 2.9940 (5.14); 2.9768 (2.28); 2.6765 (0.37); 2.6721 (0.51); 2.6677 (0.39); 2.5253 (1.72); 2.5119 (30.53); 2.5076 (61.15); 2.5030 (80.57); 2.4985 (60.37); 2.4943 (30.91); 2.3397 (16.00); 1.3381 (0.38); −0.0002 (1.45)

No. Ic-47, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.5720 (10.33); 8.5202 (0.57); 8.5058 (1.14); 8.4911 (0.57); 7.7677 (0.43); 7.7604 (3.62); 7.7558 (1.25); 7.7385 (3.88); 7.7313 (0.47); 6.9932 (0.50); 6.9860 (3.94); 6.9639 (3.74); 6.9569 (0.47); 3.9043 (1.78); 3.7980 (16.00); 3.5616 (0.71); 3.5451 (2.05); 3.5297 (2.15); 3.5136 (0.84); 3.3827 (0.35); 3.3423 (160.48); 3.1738 (1.86); 3.1564 (3.09); 3.1398 (1.32); 2.6723 (0.43); 2.5253 (1.56); 2.5075 (51.23); 2.5031 (66.51); 2.4986 (49.88); 2.4946 (25.65); 2.3342 (0.34); 2.3297 (0.46); 2.3255 (0.34); 1.2554 (0.53); 0.0077 (0.68); −0.0002 (18.18); −0.0081 (0.84)

No. Ic-48, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.9372 (0.85); 8.9224 (1.68); 8.9073 (0.84); 8.5817 (16.00); 7.9707 (3.21); 7.9543 (2.21); 7.9494 (8.73); 7.9230 (8.39); 7.9016 (3.13); 3.9047 (2.76); 3.6053 (1.08); 3.5891 (3.17); 3.5734 (3.33); 3.5574 (1.28); 3.3822 (0.37); 3.3414 (193.84); 3.3048 (0.33); 3.1955 (2.33); 3.1791 (4.63); 3.1624 (2.07); 2.6769 (0.49); 2.6723 (0.65); 2.6678 (0.49); 2.5255 (2.31); 2.5120 (39.51); 2.5078 (76.57); 2.5033 (99.56); 2.4989 (74.64); 2.3345 (0.48); 2.3299 (0.64); 2.3255 (0.47); 0.0079 (1.62); −0.0002 (41.86); −0.0084 (1.93)

No. Ic-49, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.8640 (0.84); 8.8494 (1.65); 8.8352 (0.85); 8.5904 (16.00); 7.4969 (0.33); 7.4794 (5.83); 7.4714 (2.25); 7.4606 (5.36); 7.4550 (3.52); 7.4413 (1.16); 7.4360 (0.90); 7.4297 (0.35); 3.9044 (3.18); 3.5865 (1.19); 3.5700 (3.47); 3.5544 (3.64); 3.5383 (1.38); 3.4047 (0.36); 3.3440 (282.22); 3.1865 (2.59); 3.1700 (5.19); 3.1617 (1.58); 3.1533 (2.24); 2.6770 (0.52); 2.6726 (0.68); 2.6682 (0.53); 2.5120 (43.74); 2.5079 (83.27); 2.5034 (107.58); 2.4990 (80.56); 2.4950 (41.51); 2.3346 (0.52); 2.3301 (0.71); 2.3258 (0.52); 0.0078 (1.13); −0.0002 (28.17); −0.0083 (1.33)

No. Ic-50, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.6100 (0.47); 8.5962 (0.95); 8.5826 (0.52); 8.0579 (2.10); 8.0449 (2.21); 7.8862 (1.82); 7.8808 (0.76); 7.8723 (2.02); 7.8640 (2.20); 7.8556 (0.83); 7.8502 (2.04); 7.3126 (2.06); 7.3074 (0.67); 7.2956 (0.75); 7.2903 (4.00); 7.2852 (0.92); 7.2734 (0.71); 7.2681 (2.05); 7.2605 (0.42); 6.8735 (1.40); 6.8703 (1.53); 6.8604 (1.42); 6.8573 (1.52); 6.6792 (2.64); 3.9045 (2.73); 3.8229 (0.44); 3.8106 (16.00); 3.5268 (0.81); 3.5094 (1.88); 3.4949 (1.91); 3.4774 (0.97); 3.3463 (134.26); 2.8406 (1.52); 2.8228 (2.90); 2.8051 (1.39); 2.6770 (0.42); 2.6725 (0.53); 2.6680 (0.40); 2.5258 (1.55); 2.5123 (27.87); 2.5079 (56.12); 2.5034 (74.19); 2.4989 (55.35); 2.4945 (28.09); 2.3345 (0.34); 2.3301 (0.47); 2.3256 (0.35); 1.3496 (0.54); −0.0002 (0.89)

No. Ic-51, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.4293 (0.45); 8.4153 (0.89); 8.4015 (0.44); 8.3195 (11.46); 8.0546 (2.16); 8.0415 (2.22); 7.7995 (0.40); 7.7922 (3.47); 7.7874 (1.21); 7.7750 (1.14); 7.7702 (3.75); 7.7630 (0.46); 6.9995 (0.43); 6.9922 (3.78); 6.9874 (1.28); 6.9749 (1.12); 6.9701 (3.64); 6.9632 (0.45); 6.8674 (1.42); 6.8644 (1.52); 6.8543 (1.42); 6.8513 (1.49); 6.6719 (2.68); 3.9044 (2.55); 3.8097 (15.30); 3.7984 (16.00); 3.7767 (0.75); 3.5076 (0.70); 3.4902 (1.58); 3.4759 (1.71); 3.4586 (0.86); 3.3436 (132.92); 3.3199 (5.62); 2.8316 (1.45); 2.8137 (2.76); 2.7961 (1.34); 2.6766 (0.36); 2.6720 (0.49); 2.6677 (0.38); 2.5421 (0.36); 2.5254 (1.44); 2.5118 (25.75); 2.5075 (51.93); 2.5030 (69.21); 2.4985 (52.63); 2.4944 (27.57); 2.3298 (0.42); 2.3253 (0.33); 1.2888 (0.33); −0.0002 (1.04)

No. Ic-52, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.7704 (0.62); 8.7574 (1.17); 8.7433 (0.62); 8.0608 (2.32); 8.0477 (2.51); 8.0284 (2.75); 8.0245 (2.84); 7.7978 (0.60); 7.7934 (0.49); 7.7769 (2.78); 7.7724 (3.03); 7.7662 (4.48); 7.7453 (0.78); 6.8732 (1.63); 6.8703 (1.64); 6.8602 (1.59); 6.8573 (1.58); 6.6816 (2.99); 3.9049 (3.13); 3.8122 (16.00); 3.5345 (0.86); 3.5173 (2.07); 3.5026 (2.15); 3.4853 (1.05); 3.3427 (165.20); 3.1614 (0.35); 2.8407 (1.62); 2.8231 (3.18); 2.8054 (1.50); 2.6768 (0.51); 2.6727 (0.69); 2.6681 (0.51); 2.5427 (0.46); 2.5079 (70.21); 2.5035 (90.46); 2.4990 (68.19); 2.3345 (0.43); 2.3303 (0.56); 2.3257 (0.44); −0.0002 (1.39)

No. Ic-53, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.4040 (0.71); 8.0695 (2.09); 8.0564 (2.14); 7.5573 (0.56); 7.5529 (0.74); 7.5388 (1.39); 7.5343 (1.75); 7.5254 (0.58); 7.5200 (1.33); 7.5156 (1.34); 7.5062 (0.79); 7.4997 (0.83); 7.4948 (0.44); 7.4861 (0.51); 7.4816 (0.38); 7.2937 (1.03); 7.2796 (1.20); 7.2772 (1.45); 7.2728 (1.10); 7.2691 (1.20); 7.2663 (1.18); 7.2608 (2.05); 7.2588 (1.72); 7.2480 (0.84); 7.2458 (0.90); 7.2422 (1.06); 6.8920 (1.47); 6.8889 (1.53); 6.8790 (1.44); 6.8758 (1.47); 6.6965 (2.64); 3.9044 (3.59); 3.8373 (0.67); 3.8208 (16.00); 3.8135 (1.18); 3.7876 (0.66); 3.5236 (0.82); 3.5062 (2.02); 3.4914 (2.04); 3.4741 (0.93); 3.3407 (146.64); 2.8301 (1.58); 2.8126 (3.08); 2.7951 (1.43); 2.6765 (0.46); 2.6719 (0.60); 2.6673 (0.48); 2.5420 (0.44); 2.5252 (1.83); 2.5117 (32.20); 2.5074 (64.11); 2.5028 (84.34); 2.4983 (63.12); 2.4940 (32.21); 2.3340 (0.40); 2.3296 (0.52); 2.3250 (0.40); 1.3499 (0.53); 0.0079 (0.45); −0.0002 (14.48); −0.0084 (0.62)

No. Ic-54, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.4814 (0.39); 8.0562 (0.74); 8.0432 (0.77); 7.7405 (1.13); 7.7193 (1.35); 7.4710 (1.35); 7.4498 (1.17); 6.8704 (0.50); 6.8676 (0.53); 6.8573 (0.50); 6.8545 (0.51); 6.6764 (0.95); 3.9043 (0.83); 3.8100 (5.01); 3.5050 (0.64); 3.4903 (0.65); 3.3421 (40.75); 2.8373 (0.50); 2.8197 (0.97); 2.8020 (0.46); 2.5251 (0.60); 2.5116 (10.71); 2.5074 (21.15); 2.5030 (27.87); 2.4985 (21.12); 1.2888 (16.00); −0.0002 (7.71); −0.0083 (0.38)

No. Ic-55, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.5199 (0.60); 8.0631 (1.12); 8.0500 (1.19); 6.9490 (2.89); 6.9433 (3.11); 6.8720 (0.79); 6.8691 (0.84); 6.8588 (0.82); 6.8560 (0.86); 6.6777 (1.50); 6.6354 (0.79); 6.6297 (1.47); 6.6241 (0.84); 3.9044 (1.30); 3.8119 (8.03); 3.7849 (0.47); 3.7704 (16.00); 3.7128 (0.61); 3.5084 (0.41); 3.4913 (0.99); 3.4764 (0.97); 3.4592 (0.46); 3.3475 (129.12); 2.8340 (0.78); 2.8163 (1.51); 2.7986 (0.73); 2.5078 (34.02); 2.5033 (44.27); 2.4989 (33.69); −0.0002 (2.70)

No. Ic-56, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.8483 (0.53); 8.8345 (1.09); 8.8209 (0.60); 8.1263 (2.14); 8.1155 (1.47); 8.0950 (1.40); 8.0634 (2.29); 8.0504 (2.42); 7.9135 (1.06); 7.8940 (1.30); 7.7395 (1.01); 7.7200 (1.72); 7.7005 (0.80); 6.8858 (1.51); 6.8829 (1.64); 6.8727 (1.53); 6.8699 (1.64); 6.6913 (2.93); 3.9046 (1.88); 3.8109 (16.00); 3.5633 (0.84); 3.5460 (2.03); 3.5313 (2.04); 3.5140 (0.98); 3.4003 (0.36); 3.3930 (0.53); 3.3504 (295.05); 2.8621 (1.63); 2.8445 (3.16); 2.8268 (1.52); 2.6776 (0.45); 2.6731 (0.59); 2.6689 (0.45); 2.5262 (1.80); 2.5125 (32.43); 2.5084 (63.76); 2.5040 (83.74); 2.4995 (63.47); 2.3352 (0.39); 2.3307 (0.53); 2.3263 (0.41); 1.3501 (0.45); −0.0002 (4.25)

No. Ic-57, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.4129 (0.53); 8.3992 (1.05); 8.3850 (0.54); 8.0559 (2.15); 8.0428 (2.22); 7.4053 (1.36); 7.4010 (1.54); 7.3850 (1.48); 7.3807 (1.75); 7.3610 (0.41); 7.3569 (0.40); 7.3338 (2.94); 7.3297 (2.65); 7.0144 (0.38); 6.9939 (0.42); 6.9845 (2.86); 6.9641 (2.64); 6.8628 (1.46); 6.8598 (1.53); 6.8498 (1.42); 6.8467 (1.49); 6.6686 (2.66); 6.1228 (1.67); 6.0848 (11.21); 6.0501 (0.40); 3.9041 (3.15); 3.8111 (16.00); 3.4967 (0.82); 3.4794 (1.82); 3.4648 (1.86); 3.4473 (0.93); 3.3431 (197.53); 2.8225 (1.46); 2.8048 (2.80); 2.7872 (1.34); 2.6767 (0.40); 2.6721 (0.52); 2.6677 (0.40); 2.5424 (0.45); 2.5254 (1.69); 2.5120 (28.33); 2.5076 (56.46); 2.5031 (74.69); 2.4986 (56.17); 2.4942 (28.71); 2.3344 (0.34); 2.3298 (0.47); 2.3254 (0.34); 1.3497 (0.54); −0.0002 (0.93)

No. Ic-58, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.4947 (0.57); 8.4808 (1.11); 8.4670 (0.57); 8.0559 (2.32); 8.0430 (2.36); 7.8403 (0.32); 7.8204 (0.35); 7.7333 (3.53); 7.7128 (3.90); 7.2924 (3.60); 7.2719 (3.29); 6.8704 (1.59); 6.8675 (1.66); 6.8574 (1.55); 6.8544 (1.58); 6.6759 (2.93); 3.9044 (3.18); 3.8097 (16.00); 3.5195 (0.86); 3.5021 (2.01); 3.4873 (2.05); 3.4701 (0.97); 3.3443 (128.72); 2.8377 (1.62); 2.8200 (3.06); 2.8022 (1.46); 2.6766 (0.57); 2.6683 (1.35); 2.6623 (0.65); 2.6496 (2.91); 2.6306 (3.04); 2.6119 (1.18); 2.5423 (0.37); 2.5254 (1.75); 2.5120 (31.12); 2.5078 (61.17); 2.5033 (79.91); 2.4988 (59.97); 2.3345 (0.38); 2.3300 (0.52); 2.3257 (0.38); 1.3501 (0.53); 1.2029 (4.21); 1.1839 (8.82); 1.1650 (4.04); −0.0002 (1.18)

No. Ic-59, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.2052 (0.45); 8.1914 (0.85); 8.1784 (0.48); 8.0867 (2.15); 8.0736 (2.14); 7.7105 (1.28); 7.7060 (1.40); 7.6914 (1.39); 7.6868 (1.43); 7.4735 (0.70); 7.4689 (0.72); 7.4551 (0.93); 7.4525 (1.11); 7.4508 (1.10); 7.4482 (0.97); 7.4344 (0.90); 7.4297 (0.87); 7.1179 (1.82); 7.0972 (1.59); 7.0336 (0.96); 7.0314 (1.00); 7.0146 (1.70); 7.0129 (1.73); 6.9962 (0.88); 6.9940 (0.90); 6.9085 (1.46); 6.9053 (1.52); 6.8955 (1.42); 6.8922 (1.49); 6.7149 (2.58); 3.9043 (3.43); 3.8391 (0.74); 3.8278 (16.00); 3.8117 (15.88); 3.7778 (0.65); 3.7546 (0.57); 3.5541 (0.82); 3.5368 (2.09); 3.5221 (2.11); 3.5050 (0.93); 3.3417 (161.70); 2.8361 (1.53); 2.8187 (3.07); 2.8013 (1.42); 2.6764 (0.36); 2.6719 (0.48); 2.6675 (0.36); 2.5253 (1.34); 2.5118 (26.55); 2.5074 (53.59); 2.5028 (71.13); 2.4983 (53.53); 2.4939 (27.37); 2.3340 (0.34); 2.3296 (0.47); 2.3250 (0.36); 1.3496 (0.35); −0.0002 (1.21)

No. Ic-60, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.8187 (0.60); 8.8052 (1.15); 8.7918 (0.59); 8.0620 (2.39); 8.0489 (2.48); 7.9999 (2.45); 7.9794 (3.28); 7.8601 (3.51); 7.8393 (2.58); 6.8820 (1.62); 6.8791 (1.69); 6.8689 (1.57); 6.8660 (1.62); 6.6903 (3.01); 3.9046 (2.28); 3.8428 (0.35); 3.8117 (16.00); 3.7893 (0.35); 3.5608 (0.86); 3.5435 (2.09); 3.5288 (2.10); 3.5115 (0.97); 3.3912 (0.44); 3.3839 (0.42); 3.3440 (219.39); 3.3080 (0.41); 2.8596 (1.62); 2.8420 (3.18); 2.8243 (1.47); 2.6772 (0.45); 2.6726 (0.59); 2.6682 (0.45); 2.5257 (2.01); 2.5079 (63.83); 2.5035 (83.81); 2.4991 (63.48); 2.3347 (0.39); 2.3303 (0.53); 2.3261 (0.40); 1.3501 (0.40); 0.0079 (0.66); −0.0002 (19.35); −0.0079 (0.91)

No. Ic-61, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.5199 (0.56); 8.5064 (1.03); 8.4930 (0.55); 8.0590 (2.22); 8.0459 (2.28); 7.6127 (2.21); 7.5922 (0.68); 7.5831 (0.99); 7.5805 (1.03); 7.5708 (0.85); 7.3339 (2.51); 7.3224 (3.30); 7.3202 (3.23); 6.8742 (1.55); 6.8712 (1.61); 6.8612 (1.51); 6.8582 (1.54); 6.6787 (2.80); 3.9044 (2.08); 3.8117 (16.00); 3.5215 (0.84); 3.5041 (1.99); 3.4893 (2.01); 3.4719 (0.97); 3.3444 (181.26); 2.8397 (1.60); 2.8219 (3.04); 2.8043 (1.45); 2.6765 (0.38); 2.6722 (0.50); 2.6678 (0.37); 2.5253 (1.37); 2.5117 (26.70); 2.5076 (52.59); 2.5031 (69.14); 2.4987 (52.20); 2.3639 (0.47); 2.3442 (11.80); 2.3302 (0.68); 2.3252 (0.53); 2.2700 (0.41); 1.3499 (0.54); 0.0080 (0.33); −0.0002 (10.74); −0.0083 (0.51)

No. Ic-62, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.4149 (0.79); 8.0665 (2.12); 8.0534 (2.21); 7.6462 (0.60); 7.6294 (0.71); 7.6250 (1.24); 7.6082 (1.24); 7.6039 (0.84); 7.5870 (0.67); 7.3704 (0.64); 7.3643 (0.67); 7.3466 (0.78); 7.3410 (0.93); 7.3375 (0.83); 7.3199 (0.67); 7.3137 (0.68); 7.1851 (0.58); 7.1804 (0.54); 7.1643 (1.04); 7.1586 (1.03); 7.1426 (0.53); 7.1381 (0.50); 6.8864 (1.51); 6.8833 (1.60); 6.8734 (1.49); 6.8702 (1.58); 6.6907 (2.73); 3.9044 (2.12); 3.8346 (0.59); 3.8195 (16.00); 3.7976 (0.61); 3.5183 (0.84); 3.5011 (2.06); 3.4862 (2.09); 3.4691 (0.96); 3.4066 (0.33); 3.3481 (199.38); 2.8243 (1.56); 2.8068 (3.09); 2.7893 (1.44); 2.6771 (0.41); 2.6726 (0.53); 2.6682 (0.41); 2.5257 (1.56); 2.5122 (27.46); 2.5079 (54.84); 2.5034 (72.29); 2.4989 (54.54); 2.4946 (28.23); 2.3302 (0.46); 2.3257 (0.34); 1.3497 (0.36); 0.0080 (0.36); −0.0002 (10.34); −0.0085 (0.43)

No. Ic-63, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.7609 (0.52); 8.7474 (0.98); 8.7339 (0.52); 8.3192 (0.57); 8.0641 (2.17); 8.0511 (2.23); 7.5134 (1.26); 7.5078 (2.14); 7.4920 (1.96); 7.4870 (2.03); 7.4762 (0.58); 7.4653 (0.99); 7.4595 (1.21); 7.4537 (0.51); 7.4426 (0.47); 7.4369 (0.61); 6.8765 (1.51); 6.8734 (1.56); 6.8634 (1.50); 6.8603 (1.51); 6.6857 (2.80); 3.9045 (1.70); 3.8134 (16.00); 3.5391 (0.84); 3.5217 (1.98); 3.5072 (2.00); 3.4897 (0.94); 3.4083 (0.35); 3.3518 (240.84); 2.8422 (1.55); 2.8245 (3.04); 2.8069 (1.43); 2.6774 (0.35); 2.6730 (0.45); 2.6685 (0.35); 2.5262 (1.49); 2.5127 (25.93); 2.5085 (51.13); 2.5040 (67.14); 2.4995 (50.48); 2.4954 (26.01); 2.3308 (0.43); −0.0002 (7.53); −0.0085 (0.34)

No. Ic-64, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.5421 (0.90); 8.0708 (2.18); 8.0577 (2.23); 7.6013 (0.65); 7.5942 (0.87); 7.5905 (0.78); 7.5834 (0.87); 7.5791 (0.82); 7.5722 (1.00); 7.5685 (0.86); 7.5614 (0.91); 7.5284 (1.41); 7.5215 (1.22); 7.5134 (1.47); 7.5065 (1.17); 7.3752 (1.48); 7.3513 (1.91); 7.3287 (1.25); 6.8907 (1.54); 6.8877 (1.63); 6.8777 (1.50); 6.8746 (1.57); 6.6922 (2.80); 3.9042 (3.05); 3.8382 (0.70); 3.8233 (16.00); 3.8137 (1.17); 3.8066 (0.82); 3.5172 (0.87); 3.4999 (2.19); 3.4850 (2.22); 3.4679 (1.06); 3.3436 (177.03); 3.1615 (0.32); 2.8239 (1.61); 2.8065 (3.18); 2.7890 (1.49); 2.6766 (0.41); 2.6722 (0.55); 2.6678 (0.44); 2.5428 (0.40); 2.5253 (1.87); 2.5118 (30.85); 2.5076 (61.13); 2.5031 (81.16); 2.4986 (63.04); 2.4945 (34.46); 2.3344 (0.37); 2.3298 (0.51); 2.3254 (0.39); 1.3497 (0.50); −0.0002 (1.05)

No. Ic-65, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.7007 (0.55); 8.6869 (1.06); 8.6735 (0.55); 8.0613 (2.18); 8.0482 (2.24); 7.9694 (1.51); 7.9650 (2.64); 7.9607 (1.65); 7.8089 (1.30); 7.8055 (1.04); 7.7887 (1.44); 7.7403 (0.93); 7.7380 (1.10); 7.7355 (1.05); 7.7332 (0.93); 7.7203 (1.13); 7.7181 (1.22); 7.7155 (1.27); 7.4532 (1.59); 7.4335 (2.71); 7.4138 (1.27); 6.8746 (1.53); 6.8716 (1.57); 6.8616 (1.49); 6.8585 (1.53); 6.6803 (2.78); 3.9044 (3.06); 3.8133 (16.00); 3.5315 (0.85); 3.5141 (1.99); 3.4994 (2.02); 3.4821 (0.99); 3.3922 (0.33); 3.3432 (187.48); 3.1746 (0.70); 3.1615 (0.69); 2.8420 (1.57); 2.8244 (3.05); 2.8068 (1.45); 2.6765 (0.41); 2.6722 (0.56); 2.6676 (0.42); 2.5255 (1.69); 2.5118 (30.33); 2.5076 (59.87); 2.5031 (78.61); 2.4986 (58.80); 2.4943 (29.92); 2.3344 (0.36); 2.3299 (0.50); 2.3255 (0.36); −0.0002 (1.18)

No. Ic-66, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.6640 (0.58); 8.6504 (1.12); 8.6366 (0.57); 8.0562 (2.22); 8.0432 (2.26); 7.7550 (2.87); 7.7503 (1.14); 7.7384 (1.46); 7.7335 (5.45); 7.7282 (0.99); 7.6899 (0.90); 7.6847 (5.59); 7.6798 (1.48); 7.6678 (1.10); 7.6631 (2.95); 6.8692 (1.57); 6.8661 (1.63); 6.8560 (1.54); 6.8529 (1.58); 6.6762 (2.89); 3.9044 (3.03); 3.8097 (16.00); 3.5257 (0.82); 3.5082 (2.01); 3.4935 (2.01); 3.4763 (0.94); 3.3421 (156.50); 2.8386 (1.58); 2.8208 (3.05); 2.8032 (1.44); 2.6767 (0.38); 2.6724 (0.53); 2.6679 (0.41); 2.5254 (1.57); 2.5118 (29.40); 2.5077 (57.51); 2.5032 (75.00); 2.4987 (55.92); 2.3343 (0.34); 2.3299 (0.47); 2.3256 (0.35); −0.0002 (1.31)

No. Ic-67, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.8224 (0.51); 8.8092 (0.94); 8.7961 (0.50); 8.0666 (2.17); 8.0535 (2.23); 7.5317 (0.33); 7.5150 (0.66); 7.5106 (0.64); 7.4982 (0.47); 7.4939 (1.28); 7.4772 (0.63); 7.4728 (0.78); 7.4562 (0.34); 7.1768 (0.41); 7.1690 (2.14); 7.1492 (2.84); 7.1291 (1.82); 7.1214 (0.33); 6.8948 (1.49); 6.8917 (1.60); 6.8817 (1.45); 6.8786 (1.55); 6.6950 (2.77); 3.9041 (1.84); 3.8335 (0.51); 3.8221 (16.00); 3.7863 (0.34); 3.5232 (0.86); 3.5061 (2.24); 3.4914 (2.25); 3.4745 (0.95); 3.3425 (158.00); 2.8094 (1.57); 2.7923 (3.23); 2.7751 (1.46); 2.6762 (0.32); 2.6719 (0.41); 2.5250 (1.21); 2.5116 (22.29); 2.5073 (44.89); 2.5028 (59.74); 2.4983 (45.58); 2.4941 (23.93); 2.3296 (0.39); 0.0079 (0.39); −0.0002 (11.84); −0.0083 (0.55)

No. Ic-68, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.7951 (0.52); 8.7816 (1.01); 8.7676 (0.53); 8.3195 (10.72); 8.2053 (2.61); 8.2022 (1.71); 8.1175 (1.32); 8.1137 (0.96); 8.1006 (1.06); 8.0975 (1.44); 8.0940 (1.07); 8.0640 (2.21); 8.0509 (2.28); 8.0180 (0.93); 8.0149 (1.36); 8.0116 (0.93); 7.9986 (1.08); 7.9953 (1.57); 7.7128 (1.36); 7.6933 (2.43); 7.6736 (1.11); 6.8844 (1.53); 6.8813 (1.63); 6.8713 (1.53); 6.8682 (1.57); 6.6913 (2.88); 3.9046 (1.79); 3.8135 (16.00); 3.5560 (0.78); 3.5386 (1.91); 3.5241 (1.99); 3.5068 (0.93); 3.3451 (148.24); 3.3215 (6.78); 2.8519 (1.59); 2.8343 (3.13); 2.8167 (1.47); 2.6725 (0.45); 2.6683 (0.34); 2.5257 (1.36); 2.5080 (47.49); 2.5035 (62.58); 2.4990 (47.30); 2.3303 (0.40); −0.0002 (8.66); −0.0083 (0.39)

No. Ic-69, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.5530 (0.56); 8.5395 (1.12); 8.5255 (0.61); 8.0707 (2.26); 8.0577 (2.35); 7.5022 (1.48); 7.4959 (1.50); 7.4796 (1.51); 7.4733 (1.50); 7.4125 (1.17); 7.3970 (1.26); 7.3912 (1.70); 7.3756 (1.60); 7.2918 (0.99); 7.2855 (0.94); 7.2706 (1.68); 7.2643 (1.58); 7.2493 (0.76); 7.2430 (0.69); 6.9024 (1.57); 6.8994 (1.65); 6.8893 (1.59); 6.8863 (1.64); 6.7046 (2.96); 3.9042 (2.13); 3.8345 (0.61); 3.8218 (16.00); 3.8012 (0.53); 3.5082 (0.94); 3.4910 (2.29); 3.4762 (2.37); 3.4593 (1.09); 3.3488 (256.64); 2.8220 (1.67); 2.8047 (3.33); 2.7875 (1.52); 2.6765 (0.41); 2.6723 (0.53); 2.6678 (0.42); 2.5077 (58.84); 2.5032 (76.72); 2.4988 (57.84); 2.3343 (0.35); 2.3301 (0.48); 2.3254 (0.35); 0.0079 (0.53); −0.0002 (13.34); −0.0083 (0.56)

No. Ic-70, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.8383 (0.57); 8.8248 (1.09); 8.8110 (0.57); 8.0593 (2.23); 8.0463 (2.29); 7.9751 (1.08); 7.9731 (0.86); 7.9693 (0.60); 7.9533 (8.15); 7.9461 (7.98); 7.9301 (0.56); 7.9242 (1.06); 6.8768 (1.57); 6.8737 (1.63); 6.8637 (1.54); 6.8606 (1.57); 6.6856 (2.85); 3.9044 (1.60); 3.8104 (16.00); 3.5534 (0.84); 3.5360 (2.02); 3.5215 (2.06); 3.5041 (0.95); 3.4024 (0.48); 3.3533 (219.71); 3.3176 (0.54); 3.1621 (0.32); 2.8510 (1.56); 2.8334 (3.04); 2.8158 (1.42); 2.6731 (0.39); 2.5261 (1.37); 2.5128 (22.31); 2.5085 (43.72); 2.5040 (57.22); 2.4995 (42.92); 2.4953 (22.03); 2.3308 (0.36); 0.0079 (0.33); −0.0002 (9.55); −0.0084 (0.43)

No. Ic-71, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.9204 (0.59); 8.9065 (1.15); 8.8930 (0.60); 8.3327 (0.49); 8.3267 (3.96); 8.3220 (1.38); 8.3094 (1.40); 8.3046 (4.64); 8.2991 (0.67); 8.0635 (2.37); 8.0505 (2.48); 8.0404 (0.69); 8.0346 (4.55); 8.0298 (1.52); 8.0172 (1.30); 8.0124 (3.90); 8.0067 (0.58); 6.8847 (1.59); 6.8817 (1.66); 6.8716 (1.56); 6.8687 (1.64); 6.6936 (2.98); 3.9046 (2.68); 3.8122 (16.00); 3.5692 (0.85); 3.5519 (2.08); 3.5372 (2.11); 3.5201 (0.96); 3.3890 (0.51); 3.3489 (227.87); 2.8640 (1.61); 2.8465 (3.20); 2.8289 (1.51); 2.6729 (0.43); 2.6685 (0.33); 2.5260 (1.37); 2.5125 (25.35); 2.5083 (50.35); 2.5038 (66.56); 2.4993 (50.41); 2.4953 (26.44); 2.3305 (0.43); 2.3259 (0.32); −0.0002 (0.58)

No. Ic-72, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.6756 (0.52); 8.6620 (1.00); 8.6481 (0.53); 8.0617 (2.21); 8.0487 (2.28); 7.6627 (1.25); 7.6433 (1.64); 7.6022 (0.77); 7.5960 (0.96); 7.5923 (0.76); 7.5771 (0.77); 7.5709 (0.94); 7.5670 (0.76); 7.5437 (0.67); 7.5291 (0.73); 7.5235 (1.21); 7.5089 (1.21); 7.5040 (0.77); 7.4892 (0.67); 7.4008 (0.54); 7.3988 (0.60); 7.3941 (0.54); 7.3923 (0.54); 7.3784 (0.95); 7.3720 (0.89); 7.3582 (0.44); 7.3562 (0.46); 7.3517 (0.41); 6.8770 (1.52); 6.8740 (1.61); 6.8640 (1.49); 6.8609 (1.57); 6.6839 (2.82); 3.9045 (2.04); 3.8121 (16.00); 3.5370 (0.85); 3.5196 (2.01); 3.5050 (2.03); 3.4876 (0.97); 3.3438 (157.75); 2.8454 (1.62); 2.8276 (3.12); 2.8100 (1.47); 2.6723 (0.37); 2.5255 (1.17); 2.5119 (21.60); 2.5077 (43.33); 2.5032 (57.34); 2.4987 (43.26); 2.4944 (22.30); 2.3300 (0.37); −0.0002 (0.87)

No. Ic-73, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.6887 (0.58); 8.6753 (1.06); 8.6613 (0.56); 8.0603 (2.24); 8.0472 (2.30); 7.8645 (0.62); 7.8593 (0.66); 7.8448 (0.67); 7.8395 (0.77); 7.8356 (0.75); 7.8302 (0.70); 7.8158 (0.62); 7.8107 (0.64); 7.7128 (0.58); 7.7052 (0.56); 7.7015 (0.59); 7.6945 (0.76); 7.6912 (0.75); 7.6859 (0.68); 7.6836 (0.69); 7.6798 (0.68); 7.5863 (0.71); 7.5655 (1.09); 7.5601 (0.80); 7.5444 (0.67); 7.5393 (1.06); 7.5182 (0.50); 6.8728 (1.56); 6.8699 (1.66); 6.8597 (1.53); 6.8568 (1.59); 6.6812 (2.90); 3.9046 (2.00); 3.8118 (16.00); 3.5318 (0.86); 3.5145 (2.07); 3.4998 (2.12); 3.4824 (0.98); 3.3430 (136.84); 2.8381 (1.67); 2.8205 (3.21); 2.8028 (1.52); 2.6724 (0.39); 2.5077 (47.30); 2.5033 (61.16); 2.4988 (46.03); 2.3399 (0.36); 2.3346 (0.33); 2.3301 (0.41); −0.0002 (0.99)

No. Ic-74, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.5336 (0.52); 8.5203 (0.98); 8.5059 (0.51); 8.0725 (2.20); 8.0594 (2.25); 7.4855 (0.86); 7.4824 (1.07); 7.4656 (1.94); 7.4626 (2.10); 7.4436 (0.87); 7.4391 (0.97); 7.4259 (1.41); 7.4212 (1.50); 7.4063 (0.80); 7.4014 (0.88); 7.3891 (0.88); 7.3854 (0.83); 7.3704 (1.63); 7.3671 (1.64); 7.3525 (0.94); 7.3491 (0.87); 7.3277 (1.85); 7.3234 (1.76); 7.3092 (1.05); 7.3046 (0.86); 6.9066 (1.53); 6.9035 (1.60); 6.8935 (1.50); 6.8905 (1.55); 6.7088 (2.79); 4.1169 (0.75); 4.1038 (0.77); 3.9040 (1.87); 3.8235 (16.00); 3.5112 (0.88); 3.4940 (2.24); 3.4793 (2.28); 3.4622 (0.98); 3.3434 (173.90); 3.1744 (2.73); 3.1613 (2.68); 2.8267 (1.62); 2.8094 (3.26); 2.7920 (1.47); 2.6719 (0.38); 2.5249 (1.31); 2.5114 (22.31); 2.5072 (44.38); 2.5027 (58.72); 2.4982 (44.67); 2.4940 (23.31); 2.3294 (0.38); −0.0002 (8.93); −0.0084 (0.42)

No. Ic-75, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.7040 (0.55); 8.6901 (1.02); 8.6766 (0.54); 8.0623 (2.21); 8.0493 (2.27); 7.8332 (1.44); 7.8287 (2.55); 7.8243 (1.75); 7.7701 (1.37); 7.7507 (1.55); 7.6108 (0.73); 7.6084 (0.88); 7.6057 (0.81); 7.6032 (0.78); 7.5908 (1.17); 7.5883 (1.26); 7.5857 (1.32); 7.5833 (1.10); 7.5192 (1.76); 7.4996 (2.53); 7.4799 (1.05); 6.8761 (1.53); 6.8731 (1.60); 6.8630 (1.50); 6.8600 (1.56); 6.6830 (2.83); 3.9048 (1.61); 3.8129 (16.00); 3.5349 (0.85); 3.5174 (2.04); 3.5029 (2.05); 3.4855 (0.95); 3.3389 (69.67); 2.8441 (1.61); 2.8264 (3.15); 2.8088 (1.48); 2.6722 (0.39); 2.5254 (1.26); 2.5118 (21.91); 2.5076 (43.44); 2.5031 (57.19); 2.4987 (43.40); 2.3300 (0.36); 0.0079 (0.90); −0.0002 (26.05); −0.0083 (1.26)

No. Ic-76, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.6151 (0.54); 8.6012 (1.02); 8.5879 (0.54); 8.0787 (2.24); 8.0656 (2.29); 7.7739 (1.28); 7.7546 (1.68); 7.7230 (0.56); 7.7049 (1.42); 7.6867 (1.03); 7.6489 (1.01); 7.6298 (1.27); 7.6112 (0.47); 7.4185 (1.49); 7.3999 (1.31); 6.8989 (1.54); 6.8959 (1.63); 6.8858 (1.51); 6.8828 (1.58); 6.6969 (2.86); 3.9041 (1.78); 3.8255 (16.00); 3.5078 (0.88); 3.4904 (2.17); 3.4757 (2.22); 3.4586 (1.04); 3.3489 (220.78); 2.8102 (1.59); 2.7927 (3.19); 2.7752 (1.47); 2.6722 (0.42); 2.5254 (1.45); 2.5118 (24.92); 2.5077 (49.52); 2.5032 (65.46); 2.4987 (49.73); 2.4946 (26.04); 2.3301 (0.43); −0.0002 (8.30); −0.0083 (0.40)

No. Ic-77, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.4468 (0.44); 8.4334 (0.92); 8.4193 (0.49); 8.3180 (0.39); 8.0609 (2.02); 8.0478 (2.18); 7.4383 (1.03); 7.4333 (1.27); 7.4175 (0.97); 7.4124 (1.46); 7.3931 (2.38); 7.3882 (1.93); 7.0143 (2.24); 6.9933 (1.97); 6.8734 (1.31); 6.8702 (1.43); 6.8602 (1.36); 6.8571 (1.50); 6.6768 (2.41); 3.9043 (2.36); 3.8798 (0.33); 3.8197 (1.76); 3.8114 (16.00); 3.7960 (13.14); 3.7864 (13.44); 3.7675 (0.70); 3.7606 (0.67); 3.7051 (0.37); 3.5104 (0.70); 3.4930 (1.58); 3.4780 (1.60); 3.4608 (0.85); 3.3557 (234.82); 3.3019 (0.57); 2.8359 (1.27); 2.8182 (2.37); 2.8004 (1.20); 2.6773 (0.47); 2.6729 (0.59); 2.6685 (0.45); 2.5429 (0.43); 2.5262 (1.79); 2.5127 (29.03); 2.5084 (57.83); 2.5038 (75.93); 2.4993 (56.68); 2.4949 (28.72); 2.3350 (0.34); 2.3306 (0.47); 2.3260 (0.34); 1.3498 (0.77); 1.2736 (0.39); 0.0080 (0.33); −0.0002 (8.43)

No. Ic-79, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.6622 (0.81); 8.6496 (1.56); 8.6365 (0.89); 8.5187 (0.45); 8.3246 (2.56); 8.3120 (2.69); 7.8975 (2.26); 7.8824 (2.81); 7.8761 (3.31); 7.8620 (2.70); 7.3133 (2.29); 7.2915 (4.52); 7.2694 (2.33); 7.1270 (3.80); 7.0582 (2.23); 7.0454 (2.13); 3.5230 (1.11); 3.5052 (2.74); 3.4893 (2.83); 3.4729 (1.35); 3.3482 (367.89); 2.8365 (2.27); 2.8185 (4.15); 2.8007 (2.12); 2.6726 (1.17); 2.5036 (171.29); 2.4159 (16.00); 2.3302 (1.17); −0.0002 (6.39)

No. Ic-80, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.5395 (0.64); 8.5257 (1.25); 8.5127 (0.74); 8.3400 (2.43); 8.3274 (2.58); 7.4886 (1.07); 7.4854 (1.34); 7.4688 (2.39); 7.4656 (2.71); 7.4457 (0.99); 7.4412 (1.18); 7.4279 (1.70); 7.4233 (1.94); 7.4083 (1.01); 7.4035 (1.15); 7.3926 (1.08); 7.3889 (1.16); 7.3739 (2.00); 7.3706 (2.22); 7.3559 (1.15); 7.3526 (1.20); 7.3282 (2.26); 7.3237 (2.31); 7.3099 (1.37); 7.3052 (1.25); 7.1533 (3.25); 7.0909 (1.73); 7.0793 (1.75); 3.5118 (1.09); 3.4945 (2.81); 3.4797 (2.77); 3.4626 (1.27); 3.3436 (188.70); 2.8899 (0.64); 2.8272 (2.08); 2.8097 (4.09); 2.7922 (1.95); 2.7299 (0.56); 2.6713 (0.47); 2.6669 (0.39); 2.5067 (51.98); 2.5024 (69.63); 2.4980 (55.75); 2.4310 (16.00); 2.3292 (0.47); 2.3246 (0.38); −0.0002 (3.20)

No. Ic-81, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.5983 (0.83); 8.5849 (1.56); 8.5713 (0.86); 8.3392 (2.59); 8.3266 (2.72); 8.3201 (1.07); 7.6746 (3.08); 7.6699 (3.22); 7.4945 (1.65); 7.4912 (1.45); 7.4896 (1.54); 7.4739 (2.21); 7.4706 (1.98); 7.4690 (2.11); 7.3635 (3.52); 7.3429 (2.61); 7.1483 (3.62); 7.0874 (1.94); 7.0750 (1.94); 3.5119 (1.10); 3.4949 (2.91); 3.4796 (3.01); 3.4632 (1.29); 3.4019 (0.45); 3.3481 (233.56); 2.8912 (0.36); 2.8219 (2.13); 2.8044 (4.21); 2.7871 (1.98); 2.7317 (0.35); 2.6720 (0.53); 2.5031 (79.16); 2.4295 (16.00); 2.3297 (0.53); 0.0016 (0.91); −0.0002 (1.08)

No. Ic-82, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.6880 (0.80); 8.6748 (1.53); 8.6610 (0.84); 8.3221 (3.59); 8.3118 (2.74); 7.8301 (4.31); 7.8089 (5.46); 7.7841 (0.50); 7.5485 (5.17); 7.5271 (4.74); 7.2589 (0.46); 7.2377 (0.46); 7.1241 (3.59); 7.0550 (1.91); 7.0427 (1.92); 3.5254 (1.12); 3.5081 (2.66); 3.4921 (2.71); 3.4757 (1.38); 3.3501 (198.24); 2.8905 (0.35); 2.8345 (2.16); 2.8164 (3.94); 2.7987 (2.02); 2.6724 (0.59); 2.5074 (62.66); 2.5033 (85.22); 2.4992 (72.28); 2.4393 (0.35); 2.4158 (16.00); 2.3303 (0.57); −0.0002 (3.14)

No. Ic-83, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.5086 (0.79); 8.4953 (1.51); 8.4816 (0.83); 8.3231 (2.50); 8.3105 (2.63); 7.8376 (1.74); 7.8176 (1.89); 7.7151 (4.16); 7.6949 (4.61); 7.2999 (1.59); 7.2800 (1.55); 7.2650 (4.12); 7.2452 (3.83); 7.1232 (3.52); 7.0535 (1.89); 7.0417 (1.91); 3.5135 (1.25); 3.4962 (2.76); 3.4808 (2.83); 3.4635 (1.59); 3.3555 (130.60); 2.8909 (0.97); 2.8308 (2.17); 2.8127 (3.86); 2.7949 (1.98); 2.7315 (0.84); 2.6725 (0.55); 2.5037 (77.91); 2.4159 (16.00); 2.3663 (5.84); 2.3418 (13.45); −0.0002 (0.34)

No. Ic-84, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.4163 (1.14); 8.3370 (2.55); 8.3244 (2.67); 7.5528 (0.92); 7.5348 (2.19); 7.5280 (0.98); 7.5163 (1.87); 7.5079 (1.25); 7.5023 (1.17); 7.4878 (0.68); 7.2965 (1.33); 7.2813 (1.76); 7.2758 (1.62); 7.2633 (2.87); 7.2465 (1.63); 7.1412 (3.53); 7.0772 (1.98); 7.0650 (1.99); 3.5225 (1.22); 3.5053 (2.92); 3.4897 (2.93); 3.4726 (1.44); 3.3577 (249.10); 2.8910 (0.56); 2.8281 (2.28); 2.8104 (4.26); 2.7927 (2.09); 2.7313 (0.48); 2.6729 (0.48); 2.5039 (65.74); 2.4287 (16.00); 2.3302 (0.43); −0.0002 (0.47)

No. Ic-85, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.4929 (0.51); 8.3250 (0.82); 8.3125 (0.84); 7.7408 (1.34); 7.7199 (1.55); 7.4735 (1.58); 7.4526 (1.35); 7.1284 (1.09); 7.0534 (0.58); 7.0414 (0.57); 3.5205 (0.33); 3.5031 (0.78); 3.4880 (0.78); 3.4704 (0.37); 3.3411 (33.71); 2.8908 (0.40); 2.8314 (0.64); 2.8133 (1.18); 2.7956 (0.60); 2.7315 (0.36); 2.5071 (17.42); 2.5029 (22.34); 2.4996 (17.79); 2.4194 (5.09); 1.2892 (16.00); −0.0002 (1.16)

No. Ic-86, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

20.0038 (1.14); 8.6741 (1.13); 8.6148 (0.77); 8.3299 (2.01); 8.3171 (2.16); 7.6618 (1.42); 7.6433 (1.99); 7.5956 (1.16); 7.5722 (1.17); 7.5262 (1.23); 7.5115 (1.30); 7.3799 (1.18); 7.1312 (2.85); 7.0600 (1.47); 7.0492 (1.61); 3.5170 (2.29); 3.5022 (2.39); 3.4834 (1.55); 3.3415 (5739.85); 2.8398 (2.22); 2.8213 (3.69); 2.8028 (2.20); 2.6716 (16.00); 2.5068 (1843.93); 2.5025 (2321.81); 2.4983 (1770.85); 2.4183 (14.24); 2.3293 (15.15); 1.2356 (0.75); −0.0002 (113.32)

No. Ic-87, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.8632 (0.81); 8.8503 (1.51); 8.8362 (0.84); 8.3314 (2.60); 8.3188 (2.69); 8.1272 (3.12); 8.0969 (1.94); 7.9162 (1.49); 7.8968 (1.81); 7.7413 (1.31); 7.7219 (2.21); 7.7028 (1.00); 7.1368 (3.61); 7.0705 (1.94); 7.0582 (1.91); 3.5597 (1.07); 3.5421 (2.65); 3.5264 (2.67); 3.5098 (1.27); 3.3826 (0.69); 3.3460 (245.64); 2.8559 (2.15); 2.8378 (4.01); 2.8201 (2.02); 2.6728 (0.55); 2.5034 (78.20); 2.4995 (67.27); 2.4397 (0.34); 2.4158 (16.00); 2.3304 (0.52); −0.0002 (3.03); −0.0019 (2.43)

No. Ic-88, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.5058 (0.77); 8.4922 (1.53); 8.4789 (0.86); 8.3237 (2.48); 8.3112 (2.61); 7.7335 (4.14); 7.7130 (4.77); 7.2947 (4.24); 7.2742 (4.05); 7.1251 (3.49); 7.0533 (1.85); 7.0414 (1.89); 3.5167 (1.10); 3.4995 (2.50); 3.4839 (2.51); 3.4669 (1.26); 3.3976 (0.36); 3.3472 (205.91); 2.8313 (2.13); 2.8132 (3.81); 2.7954 (1.97); 2.6696 (1.56); 2.6504 (3.55); 2.6315 (3.65); 2.6128 (1.40); 2.5072 (52.43); 2.5031 (67.83); 2.4990 (54.27); 2.4172 (16.00); 2.3299 (0.45); 1.2027 (4.65); 1.1940 (1.19); 1.1838 (9.58); 1.1647 (4.46); −0.0002 (2.84)

No. Ic-89, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.3541 (1.81); 8.3415 (1.85); 8.2141 (0.43); 8.2012 (0.78); 8.1883 (0.45); 7.7123 (1.31); 7.7078 (1.41); 7.6931 (1.41); 7.6886 (1.45); 7.4744 (0.81); 7.4698 (0.81); 7.4559 (0.93); 7.4533 (1.11); 7.4518 (1.07); 7.4491 (0.93); 7.4352 (0.87); 7.4306 (0.82); 7.1547 (2.25); 7.1204 (1.96); 7.0995 (1.87); 7.0941 (1.37); 7.0804 (1.19); 7.0351 (0.98); 7.0330 (0.96); 7.0163 (1.69); 7.0145 (1.67); 6.9978 (0.90); 6.9956 (0.85); 6.9855 (0.33); 3.9050 (1.10); 3.8086 (16.00); 3.5580 (0.85); 3.5405 (1.99); 3.5258 (2.02); 3.5082 (1.00); 3.3358 (55.29); 2.8326 (1.54); 2.8149 (2.97); 2.7972 (1.41); 2.6759 (0.34); 2.6714 (0.47); 2.6669 (0.35); 2.5247 (1.50); 2.5112 (26.66); 2.5068 (52.90); 2.5023 (70.07); 2.4978 (52.92); 2.4935 (27.14); 2.4349 (12.42); 2.3335 (0.33); 2.3291 (0.45); 2.3246 (0.34); 0.0081 (0.89); −0.0002 (26.75); −0.0084 (1.07)

No. Ic-90, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.8319 (0.80); 8.8189 (1.51); 8.8052 (0.80); 8.3304 (2.54); 8.3177 (2.61); 7.9994 (3.15); 7.9791 (4.19); 7.8628 (4.34); 7.8422 (3.27); 7.1366 (3.46); 7.0662 (1.84); 7.0541 (1.80); 3.5577 (1.09); 3.5403 (2.56); 3.5248 (2.57); 3.5079 (1.25); 3.4042 (0.33); 3.3461 (260.63); 3.2945 (0.38); 2.8540 (2.06); 2.8360 (3.84); 2.8183 (1.94); 2.6725 (0.60); 2.5075 (65.69); 2.5034 (87.06); 2.4998 (71.81); 2.4432 (0.37); 2.4199 (16.00); 2.3303 (0.58); −0.0002 (3.62)

No. Ic-91, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.7185 (0.75); 8.7051 (1.41); 8.6916 (0.79); 8.3298 (2.54); 8.3172 (2.64); 7.8747 (0.76); 7.8575 (0.34); 7.8268 (3.15); 7.7697 (1.76); 7.7504 (2.06); 7.6108 (1.22); 7.6086 (1.21); 7.5909 (1.71); 7.5885 (1.82); 7.5212 (2.10); 7.5015 (3.07); 7.4820 (1.31); 7.1288 (3.46); 7.0611 (1.83); 7.0487 (1.83); 3.5314 (1.16); 3.5139 (2.69); 3.4984 (2.70); 3.4815 (1.40); 3.4586 (0.33); 3.3504 (98.15); 2.8381 (2.15); 2.8200 (3.95); 2.8022 (2.00); 2.6720 (0.47); 2.5033 (66.97); 2.4993 (54.96); 2.4193 (16.00); 2.3299 (0.44); −0.0002 (2.34)

No. Ic-92, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.8157 (0.80); 8.8026 (1.51); 8.7896 (0.82); 8.3338 (2.56); 8.3212 (2.65); 7.9535 (0.45); 7.9147 (0.80); 7.8631 (2.02); 7.8597 (1.73); 7.8101 (12.00); 7.1312 (3.53); 7.0643 (1.89); 7.0522 (1.89); 3.5328 (1.44); 3.5156 (3.04); 3.5004 (3.17); 3.4833 (1.88); 3.3601 (116.66); 2.8919 (2.65); 2.8353 (2.17); 2.8175 (3.99); 2.7998 (2.00); 2.7322 (2.41); 2.6734 (0.57); 2.5046 (84.12); 2.4561 (0.39); 2.4223 (16.00); 2.3311 (0.55)

No. Ic-93, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.5340 (0.77); 8.5204 (1.44); 8.5066 (0.81); 8.3271 (2.49); 8.3145 (2.62); 7.6126 (3.04); 7.5928 (0.92); 7.5900 (0.92); 7.5818 (1.46); 7.5718 (1.28); 7.3555 (0.41); 7.3360 (3.07); 7.3244 (4.20); 7.3224 (4.79); 7.1266 (3.48); 7.0573 (1.86); 7.0449 (1.85); 3.5184 (1.09); 3.5009 (2.54); 3.4842 (2.54); 3.4682 (1.28); 3.3425 (95.37); 2.8329 (2.14); 2.8147 (3.86); 2.7969 (1.99); 2.6719 (0.41); 2.5072 (43.88); 2.5029 (60.03); 2.4988 (50.28); 2.4188 (16.00); 2.3458 (15.04); −0.0002 (2.97)

No. Ic-94, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.4242 (1.09); 8.3348 (2.47); 8.3222 (2.59); 7.6466 (0.69); 7.6254 (1.53); 7.6085 (1.49); 7.6045 (1.13); 7.5873 (0.79); 7.3734 (0.80); 7.3672 (0.87); 7.3494 (1.01); 7.3440 (1.27); 7.3406 (1.13); 7.3228 (0.83); 7.3167 (0.88); 7.1881 (0.74); 7.1832 (0.76); 7.1674 (1.39); 7.1620 (1.41); 7.1456 (0.84); 7.1346 (3.49); 7.0699 (1.79); 7.0576 (1.79); 3.5164 (1.09); 3.4991 (2.65); 3.4839 (2.67); 3.4666 (1.26); 3.3447 (88.40); 2.8216 (2.11); 2.8037 (4.01); 2.7861 (1.96); 2.6723 (0.45); 2.5075 (48.38); 2.5031 (63.37); 2.4989 (49.92); 2.4266 (16.00); 2.3297 (0.40); −0.0002 (3.09)

No. Ic-95, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.7667 (0.77); 8.7540 (1.39); 8.7402 (0.77); 8.3334 (2.53); 8.3208 (2.60); 7.5247 (0.50); 7.5081 (2.95); 7.4926 (3.31); 7.4878 (2.88); 7.4763 (0.76); 7.4704 (1.52); 7.4647 (1.54); 7.4478 (0.63); 7.4421 (0.78); 7.1315 (3.41); 7.0625 (1.83); 7.0498 (1.82); 3.5364 (1.12); 3.5192 (2.57); 3.5041 (2.58); 3.4865 (1.26); 3.3429 (73.33); 2.8913 (1.02); 2.8372 (2.14); 2.8192 (3.90); 2.8013 (1.99); 2.7319 (0.90); 2.6726 (0.41); 2.5075 (49.94); 2.5034 (62.04); 2.4199 (16.00); 2.3299 (0.43); −0.0002 (2.53)

No. Ic-96, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.5914 (0.73); 8.5779 (1.31); 8.5640 (0.70); 8.0711 (2.43); 8.0581 (2.47); 7.6725 (2.76); 7.6677 (2.79); 7.4911 (1.49); 7.4861 (1.41); 7.4706 (2.02); 7.4656 (1.92); 7.3630 (3.36); 7.3425 (2.47); 6.8990 (1.84); 6.8882 (1.78); 6.7046 (3.36); 3.8214 (16.00); 3.8043 (0.67); 3.5108 (0.99); 3.4938 (2.53); 3.4788 (2.60); 3.4620 (1.11); 3.3374 (72.52); 2.8904 (0.64); 2.8203 (1.83); 2.8030 (3.63); 2.7858 (1.70); 2.7309 (0.57); 2.6713 (0.48); 2.6672 (0.37); 2.5066 (54.26); 2.5024 (68.54); 2.4982 (52.98); 2.3293 (0.44); −0.0002 (3.72)

No. Ic-97, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.4928 (0.68); 8.4790 (1.26); 8.4650 (0.66); 8.0547 (2.32); 8.0417 (2.37); 7.8287 (0.55); 7.8084 (0.60); 7.7140 (3.60); 7.6936 (3.99); 7.2820 (0.49); 7.2622 (3.73); 7.2424 (3.12); 6.8661 (1.82); 6.8559 (1.63); 6.8530 (1.76); 6.6735 (3.14); 3.8088 (16.00); 3.5153 (0.94); 3.4980 (2.21); 3.4830 (2.21); 3.4660 (1.06); 3.3412 (65.07); 2.8903 (0.86); 2.8359 (1.73); 2.8182 (3.30); 2.8007 (1.62); 2.7304 (0.73); 2.6717 (0.44); 2.5072 (48.56); 2.5028 (65.10); 2.4984 (52.31); 2.3597 (1.91); 2.3399 (11.16); −0.0002 (3.49)

No. Ic-98, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.3146 (0.87); 8.3016 (1.57); 8.2890 (0.97); 8.0709 (2.51); 8.0580 (2.68); 7.3169 (0.54); 7.3104 (0.65); 7.2968 (1.43); 7.2926 (1.42); 7.2814 (1.22); 7.2765 (1.46); 7.2098 (6.28); 7.1952 (3.68); 7.1731 (0.78); 7.1493 (0.51); 6.8951 (2.25); 6.8823 (2.31); 6.6939 (3.94); 3.8208 (16.00); 3.7826 (0.57); 3.5152 (1.37); 3.4985 (3.32); 3.4834 (3.45); 3.4670 (1.72); 3.3489 (100.35); 2.8905 (0.37); 2.8266 (2.26); 2.8096 (4.30); 2.7926 (2.13); 2.7302 (0.35); 2.6720 (0.64); 2.5028 (80.08); 2.4451 (2.27); 2.3297 (0.58); 2.2229 (14.11); −0.0002 (2.35)

No. Ic-99, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.8037 (0.70); 8.7905 (1.37); 8.7770 (0.76); 8.3192 (1.36); 8.0637 (2.43); 8.0507 (2.54); 7.8097 (16.00); 6.8733 (2.03); 6.8602 (2.02); 6.6830 (3.53); 3.8145 (15.95); 3.5350 (0.95); 3.5177 (2.39); 3.5028 (2.39); 3.4860 (1.13); 3.3531 (239.97); 2.8910 (1.09); 2.8387 (1.84); 2.8212 (3.59); 2.8036 (1.73); 2.7309 (0.97); 2.6727 (0.45); 2.5082 (47.10); 2.5039 (64.66); 2.4998 (54.89); 2.3307 (0.44); −0.0002 (2.24)

No. Ic-100, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.4744 (1.04); 8.3207 (0.97); 8.0676 (2.40); 8.0546 (2.46); 7.5804 (1.22); 7.5606 (3.76); 7.5398 (1.75); 7.5354 (1.71); 7.5306 (1.60); 7.3819 (1.62); 7.3770 (1.54); 7.3611 (1.32); 7.3561 (1.27); 6.8858 (1.84); 6.8832 (1.72); 6.8727 (1.80); 6.6916 (3.31); 3.8343 (0.59); 3.8193 (16.00); 3.8007 (0.51); 3.5197 (0.91); 3.5027 (2.30); 3.4876 (2.38); 3.4706 (1.00); 3.3421 (101.47); 2.8233 (1.78); 2.8058 (3.49); 2.7883 (1.62); 2.6722 (0.41); 2.5073 (48.31); 2.5029 (60.55); 2.4985 (45.52); 2.3299 (0.40); −0.0002 (3.29)

No. Ic-101, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.4281 (0.84); 8.4145 (1.59); 8.4011 (0.86); 8.3247 (2.54); 8.3121 (2.65); 7.4062 (1.77); 7.4021 (1.87); 7.3859 (1.92); 7.3818 (2.07); 7.3350 (3.82); 7.3315 (3.38); 7.1181 (3.52); 7.0473 (1.87); 7.0354 (1.90); 6.9882 (3.34); 6.9679 (3.05); 6.0865 (12.92); 3.4944 (1.09); 3.4772 (2.51); 3.4618 (2.59); 3.4444 (1.23); 3.3441 (173.45); 2.8909 (0.42); 2.8169 (2.11); 2.7988 (3.80); 2.7810 (1.95); 2.7315 (0.40); 2.6722 (0.45); 2.5071 (54.72); 2.5030 (68.01); 2.4175 (16.00); 2.3299 (0.45); −0.0002 (2.87)

No. Ic-102, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.4417 (0.74); 8.4281 (1.39); 8.4146 (0.77); 8.3236 (2.21); 8.3110 (2.28); 7.7936 (3.85); 7.7715 (4.09); 7.1218 (3.12); 7.0521 (1.69); 7.0394 (1.69); 6.9950 (4.13); 6.9730 (3.91); 3.7993 (16.00); 3.5054 (0.98); 3.4883 (2.22); 3.4726 (2.33); 3.4554 (1.13); 3.3474 (151.20); 2.8909 (0.47); 2.8256 (1.87); 2.8076 (3.34); 2.7897 (1.74); 2.7317 (0.42); 2.6722 (0.38); 2.5032 (56.46); 2.4169 (13.85); 2.3300 (0.39); −0.0002 (2.09)

No. Ic-103, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.9318 (0.76); 8.9185 (1.45); 8.9045 (0.81); 8.3296 (5.90); 8.3197 (3.14); 8.3072 (5.51); 8.0339 (5.14); 8.0116 (4.58); 7.1396 (3.35); 7.0694 (1.77); 7.0573 (1.79); 3.5661 (1.05); 3.5487 (2.50); 3.5334 (2.52); 3.5163 (1.21); 3.4048 (0.32); 3.3886 (0.54); 3.3490 (217.85); 2.8911 (1.77); 2.8588 (2.06); 2.8409 (3.83); 2.8231 (1.95); 2.7314 (1.50); 2.6769 (0.35); 2.6725 (0.44); 2.6689 (0.35); 2.5079 (49.33); 2.5036 (64.55); 2.4994 (51.21); 2.4439 (0.32); 2.4214 (16.00); 2.3303 (0.43); 2.3262 (0.35); −0.0002 (2.64)

No. Ic-104, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.3376 (2.60); 8.3249 (3.14); 8.3072 (1.47); 8.2934 (0.79); 7.3181 (0.53); 7.3101 (0.56); 7.3043 (0.77); 7.2976 (1.24); 7.2917 (1.10); 7.2834 (1.06); 7.2773 (1.31); 7.2111 (6.16); 7.2037 (3.09); 7.1965 (3.63); 7.1761 (0.38); 7.1414 (3.47); 7.0813 (1.82); 7.0690 (1.85); 3.5166 (1.16); 3.4994 (2.98); 3.4844 (2.95); 3.4675 (1.31); 3.3801 (0.72); 3.3474 (193.07); 3.3030 (0.43); 2.8900 (0.41); 2.8259 (2.19); 2.8085 (4.25); 2.7910 (2.01); 2.7300 (0.37); 2.6715 (0.37); 2.5068 (42.64); 2.5025 (56.75); 2.4983 (45.92); 2.4279 (16.00); 2.3293 (0.38); 2.2251 (14.99); −0.0002 (2.33)

No. Ic-105, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.6632 (0.68); 8.6497 (1.26); 8.6360 (0.67); 8.0582 (2.41); 8.0452 (2.48); 7.8270 (4.04); 7.8055 (4.54); 7.5480 (4.73); 7.5266 (3.89); 6.8721 (1.79); 6.8591 (1.77); 6.6792 (3.28); 3.8100 (16.00); 3.5295 (0.96); 3.5123 (2.33); 3.4974 (2.42); 3.4801 (1.17); 3.3522 (227.85); 2.8913 (1.92); 2.8409 (1.77); 2.8232 (3.43); 2.8055 (1.66); 2.7319 (1.69); 2.6771 (0.33); 2.6730 (0.40); 2.5081 (48.56); 2.5038 (61.15); 2.4995 (46.32); 2.3307 (0.40); −0.0002 (2.38)

No. Ic-106, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.5791 (0.72); 8.5659 (1.32); 8.5528 (0.76); 8.3184 (0.59); 8.0607 (2.43); 8.0478 (2.54); 7.8032 (3.34); 7.7855 (3.67); 7.5355 (0.54); 7.5175 (1.75); 7.4994 (1.62); 7.4704 (2.82); 7.4516 (3.71); 7.4339 (1.43); 6.8779 (1.95); 6.8655 (1.95); 6.6850 (3.56); 3.8109 (16.00); 3.5344 (1.09); 3.5172 (2.58); 3.5021 (2.65); 3.4851 (1.30); 3.3569 (313.73); 3.2775 (0.40); 2.8482 (2.00); 2.8305 (3.80); 2.8129 (1.89); 2.6728 (0.48); 2.5038 (70.94); 2.3308 (0.47); −0.0002 (0.70)

No. Ic-107, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.5856 (16.00); 8.5665 (4.63); 8.5527 (2.59); 8.4591 (9.13); 8.4469 (9.47); 7.4846 (4.04); 7.4651 (8.76); 7.4433 (12.12); 7.4309 (13.60); 7.4115 (3.07); 7.4063 (3.50); 7.3964 (3.10); 7.3929 (3.00); 7.3776 (6.56); 7.3747 (6.63); 7.3602 (4.71); 7.3566 (5.58); 7.3527 (8.73); 7.3480 (8.20); 7.3340 (3.36); 7.3292 (2.77); 3.8097 (0.58); 3.7980 (0.93); 3.5808 (3.54); 3.5641 (9.69); 3.5489 (10.06); 3.5324 (4.29); 3.3477 (627.52); 3.2563 (0.39); 3.0062 (7.11); 2.9892 (14.00); 2.9722 (6.60); 2.8908 (1.37); 2.7312 (1.20); 2.6722 (1.25); 2.5070 (145.79); 2.5031 (185.98); 2.4992 (150.12); 2.3297 (1.25); −0.0002 (7.24)

No. Ic-108, Solvent: <[D₆]-DMSO>, Spectrometer: 601.6 MHz

8.5872 (2.38); 8.5781 (4.34); 8.5691 (2.34); 8.3223 (11.25); 8.3139 (11.44); 7.7653 (6.55); 7.7523 (7.93); 7.7173 (3.00); 7.7050 (7.13); 7.6925 (4.51); 7.6426 (4.39); 7.6298 (6.46); 7.6172 (2.60); 7.4273 (13.17); 7.4265 (13.22); 7.4059 (7.12); 7.3934 (6.53); 7.3285 (7.38); 7.3264 (7.05); 7.3201 (7.23); 7.3180 (6.78); 3.9026 (8.22); 3.5487 (4.53); 3.5376 (11.20); 3.5278 (11.37); 3.5168 (4.82); 3.3172 (360.46); 3.1722 (0.99); 3.1635 (0.97); 2.8807 (8.05); 2.8694 (16.00); 2.8582 (7.52); 2.6185 (1.53); 2.6156 (3.11); 2.6125 (4.28); 2.6095 (3.11); 2.6066 (1.49); 2.5401 (1.17); 2.5218 (9.07); 2.5188 (11.15); 2.5156 (11.72); 2.5068 (234.71); 2.5038 (493.13); 2.5008 (673.77); 2.4978 (492.69); 2.4948 (230.18); 2.3910 (1.30); 2.3880 (2.87); 2.3850 (3.98); 2.3820 (2.80); 2.3791 (1.23); 1.2362 (0.46); 0.0965 (1.98); 0.0200 (0.36); 0.0052 (16.40); −0.0002 (483.17); −0.0057 (15.23); −0.1000 (1.97)

No. Ic-109, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.8744 (2.27); 8.8502 (2.40); 8.3175 (1.28); 7.7482 (3.28); 7.7335 (4.35); 7.7285 (5.09); 7.7165 (2.82); 7.6489 (2.42); 7.6294 (3.15); 7.6108 (1.34); 7.3008 (3.72); 7.2810 (3.02); 4.5767 (1.53); 4.5535 (1.51); 3.9039 (16.00); 3.5063 (1.08); 3.4624 (2.31); 3.4544 (1.70); 3.4285 (2.77); 3.3493 (2090.58); 3.1742 (0.87); 3.1611 (0.76); 2.8910 (0.38); 2.7110 (1.42); 2.6766 (2.85); 2.6721 (3.86); 2.6677 (2.94); 2.5075 (445.81); 2.5031 (581.82); 2.4986 (439.71); 2.4247 (0.83); 2.3918 (1.17); 2.3627 (1.15); 2.3342 (3.09); 2.3298 (4.07); 2.3254 (3.14); 1.8532 (1.48); 1.8353 (2.10); 1.8106 (4.24); 1.7791 (3.94); 1.7357 (1.65); 1.7103 (1.49); 1.5723 (0.32); 1.5286 (1.74); 1.5047 (1.15); 1.4051 (1.11); 1.3762 (1.02); 1.2976 (0.40); 1.2580 (0.66); 1.2349 (1.39); 0.8401 (2.15); 0.8349 (2.19); 0.8268 (0.98); 0.0079 (1.57); −0.0002 (38.93); −0.0084 (1.55)

The following tables D to F illustrate in a non limiting manner intermediates of formula (II) which can be used for the preparation of compounds of formula (I).

TABLE D

Compounds of formula (IIa)

(IIa)

embedded image

Reference or phys.

No.
X_n
R¹
R²
R³
R⁴
R⁵
salt
chem. data

IIa-1
3-Cl
C₂H₅
H
H
H
H
HCl-salt
P2

5-CF₃

P10

IIa-2
3-Cl
CH₃
H
H
H
H

according to P2, not

5-CF₃

isolated

IIa-3
5-CF₃
CH₃
H
H
H
H
HCl-salt
NMR

IIa-4
5-CF₃
CH₃
H
H
H
H

according to P2, not

6-Cl

isolated

IIa-5
5-Cl
CH₃
H
H
H
H

P11

IIa-6
3-Cl
CH₃
H
H
H
H

NMR

5-Cl

IIa-7
3-Cl
n-Pr
H
H
H
H

according to P10, not

5-CF₃

isolated

IIa-8
5-Cl
C₆H₅
H
H
H
H

IIa-9
3-Cl
NHC(O)—CH₃
H
H
H
H

P2

5-CF₃

P10

IIa-10
3-Cl
NHC(O)—2-C₆H₄Cl
H
H
H
H

according to P2, P10

5-CF₃

IIa-11
3-Cl
NHC(O)—2,6-C₆H₃Cl₂
H
H
H
H

according to P2, P10

5-CF₃

IIa-12
3-Cl
OH
H
COOC₂H₅
H
H

5-CF₃

IIa-13
3-Cl
OH
H
H
H
H

P2

5-CF₃

P10

IIa-14
3-Cl
F
F
H
H
H

NMR

5-CF₃

see Examples

IIa-15
3-Cl
F
F
H
H
H

NMR

5-Cl

see Examples

IIa-16
3-Cl
CH₃
H
CH₃
H
H

NMR

5-CF₃

see Examples

IIa-17
3-Cl
CH₂-cyclo-Pr
H
CH₃
H
H

NMR

5-CF₃

IIa-18
3-Cl
CH₂—CH═CH₂
H
CH₃
H
H

NMR

5-CF₃

IIa-19
3-Cl
CH₂—C≡CH
H
CH₃
H
H

NMR

5-CF₃

IIa-20
3-Cl
H
H
C₂H₅
H
H

P2

5-CF₃

P10

IIa-21
3-Cl
H
H
CH₃
H
H

according to P2, P10

5-CF₃

IIa-22
3-Cl
H
H
CH₃
H
H

[M + 1] = 205

5-Cl

IIa-23
6-Cl
H
H
CH₃
H
H

[M + 1] = 239

5-CF₃

IIa-24
3-Cl
H
H
CH₃
H
cyclo-Pr
HCl salt
P2

5-CF₃

P10

NMR

IIa-25
3-Cl
H
H
C₆H₅
H
H

P2

5-CF₃

P10

IIa-26
3-Cl
H
H
COOH
H
H

comm av.

5-CF₃

CAS-No. 317377-64-3

NMR

IIa-27
3-Cl
H
H
COOMe
H
H

P1

5-CF₃

comm av.

CAS-No. 1008232-30-1

IIa-28
3-Cl
H
H
COOEt
H
H

according to P1

5-CF₃

IIa-29
3-Cl
H
H
CONHMe
H
H

according to P1

5-CF₃

IIa-30
3-Cl
H
H
CONHEt
H
H

according to P1

5-CF₃

NMR

IIa-31
5-CF₃
CH₂—CH₂
H
H
H

IIa-32
3-Cl
CH₂—CH₂
H
H
H
—

5-Cl

IIa-33
5-Cl
CH₂—CH₂
H
H
H
—

IIa-34
5-Cl
(CH₂)₄
H
H
H
—

IIa-35
3-Cl
H
CH₂
H
COO—C₄H₉-t
—
P5

5-Cl

H

IIa-36
3-Cl
H
(CH₂)₄
H
H
—
P5

5-Cl

IIa-37
3-Cl
H
(CH₂)₄
H
H
—
P4

5-CF₃

IIa-38
3-Cl
H
(CH₂)₅
H
H
—
P4

5-CF₃

IIa-39
3-Cl
H
H
H
H
cyclo-Pr

P9

5-CF₃

IIa-40
3-Cl
N(CH₃)₂
H
H
H
H
2 HCl
According to J. Amer.

5-CF₃

Chem. Soc. 72, 2804-6

(1950);

WO 1984/03278

WO 2008/06479

THL 45, 7407-08

(2004) NMR

IIa-41
3-Cl 5-CF₃

embedded image

H
H
H
H
2 HCl
According to J. Amer. Chem. Soc. 72, 2804-6 (1950); WO 1984/03278

WO 2008/06479

THL 45, 7407-08

(2004) NMR

¹H-NMR Data

No. IIa-3, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.9425 (4.53); 8.5297 (0.55); 8.3132 (0.37); 8.3081 (0.36); 8.2919 (0.35); 8.2871 (0.34); 8.2274 (2.43); 8.2220 (2.47); 8.2066 (2.63); 8.2014 (2.57); 7.9233 (3.03); 7.9035 (1.80); 7.8274 (0.51); 7.6396 (4.25); 7.6190 (3.98); 7.3355 (0.94); 7.2080 (1.11); 7.0806 (0.95); 3.9056 (6.21); 3.5088 (0.47); 3.3780 (460.23); 3.3398 (2.99); 3.3213 (1.08); 3.3038 (0.56); 3.2802 (0.50); 3.2660 (0.94); 3.2515 (1.14); 3.2344 (1.49); 3.2202 (1.32); 3.2154 (1.20); 3.2005 (0.91); 3.1668 (2.48); 3.1300 (0.34); 3.1160 (1.18); 3.1012 (1.89); 3.0859 (1.76); 3.0701 (1.36); 3.0550 (0.71); 2.6777 (1.01); 2.6732 (1.39); 2.6687 (1.05); 2.6173 (0.39); 2.5383 (15.01); 2.5244 (34.14); 2.5127 (88.01); 2.5087 (171.64); 2.5041 (220.28); 2.4996 (165.79); 2.4953 (85.87); 2.3354 (1.00); 2.3308 (1.41); 2.3264 (1.01); 2.0215 (0.61); 1.4956 (2.91); 1.2936 (16.00); 1.2762 (15.82); −0.0002 (1.03)

No. IIa-6, Solvent: <[D₆]-DMSO>, Spectrometer: 250 MHz

8.5963 (8.43); 8.2402 (10.03); 8.1164 (7.73); 5.3630 (6.41); 3.6596 (3.33); 3.4600 (0.33); 3.2465 (2.97); 3.0224 (2.94); 2.4999 (4.52); 1.1822 (16.00); 0.9220 (0.39)

No. IIa-17, Solvent: <CDCl₃>, Spectrometer: 250 MHz

8.9941 (2.31); 8.9630 (0.34); 8.1671 (3.06); 8.1606 (2.59); 7.5175 (16.00); 5.5564 (0.32); 3.9536 (0.69); 3.7988 (0.70); 3.7839 (0.96); 3.7718 (0.94); 3.7565 (1.47); 3.7409 (0.76); 3.7291 (0.99); 3.7140 (0.88); 3.7011 (0.63); 3.6746 (0.72); 3.6478 (0.48); 3.5960 (0.37); 3.5702 (1.39); 3.5440 (1.89); 3.5178 (1.27); 2.2067 (0.53); 2.1840 (0.70); 2.1558 (1.59); 2.1299 (2.84); 2.1145 (3.46); 2.0400 (0.86); 2.0115 (0.72); 1.9919 (0.95); 1.9754 (1.13); 1.9497 (0.99); 1.9382 (1.01); 1.9106 (0.97); 1.8963 (0.69); 1.8588 (0.34); 1.5092 (1.77); 1.4234 (3.14); 1.3975 (3.07); 1.2784 (8.41); 1.2526 (8.28); 1.2064 (0.53); 1.1338 (0.43); 1.1081 (0.40); 1.0670 (0.55); 1.0434 (0.55); 0.9228 (0.36); 0.7034 (0.40); 0.6727 (0.65); 0.6423 (0.86); 0.6352 (0.88); 0.6164 (1.21); 0.5976 (1.53); 0.5835 (1.25); 0.5621 (1.09); 0.5265 (0.65); 0.5116 (0.84); 0.4908 (1.06); 0.4746 (1.28); 0.4604 (1.03); 0.4450 (0.92); 0.4378 (0.80); 0.4077 (0.47); 0.3041 (0.41); 0.2821 (0.68); 0.2671 (1.08); 0.2469 (1.08); 0.2339 (0.94); 0.0354 (0.52); 0.0164 (1.14); 0.0006 (1.38); 0.0203 (1.36); 0.0372 (0.95); 0.0580 (0.55)

No. IIa-18, Solvent: <CDCl₃>, Spectrometer: 250 MHz

8.9427 (3.26); 8.0878 (4.75); 7.4633 (16.00); 5.8995 (0.57); 5.8721 (1.11); 5.8589 (0.73); 5.8440 (0.67); 5.8314 (1.96); 5.8036 (2.06); 5.7908 (0.90); 5.7757 (0.84); 5.7635 (1.57); 5.7353 (0.80); 5.1250 (2.37); 5.1181 (2.31); 5.0738 (1.08); 5.0563 (3.92); 5.0193 (2.01); 3.7000 (1.05); 3.6740 (1.88); 3.6485 (1.68); 3.6408 (1.67); 3.6150 (1.40); 3.5866 (0.93); 3.5604 (1.19); 3.5494 (0.72); 3.5338 (0.83); 3.5235 (2.12); 3.4975 (2.89); 3.4713 (1.78); 3.4452 (0.46); 2.8940 (1.26); 2.8800 (1.38); 2.8592 (3.43); 2.8305 (2.50); 2.7877 (1.03); 2.7576 (1.18); 2.7350 (0.58); 1.6222 (4.44); 1.4911 (0.38); 1.4546 (0.73); 1.3640 (5.48); 1.3382 (5.36); 1.2214 (13.13); 1.1957 (13.11); 1.0405 (0.42); 1.0155 (0.41)

No. IIa-19, Solvent: <CDCl₃>, Spectrometer: 250 MHz

8.7504 (1.99); 8.6893 (4.95); 8.6001 (0.38); 7.8894 (1.68); 7.8607 (5.20); 7.2799 (0.39); 7.1935 (23.30); 7.1061 (0.38); 5.2314 (0.41); 4.6008 (0.71); 4.5754 (0.71); 4.5664 (0.95); 4.5408 (0.72); 3.7272 (0.50); 3.6408 (12.39); 3.6111 (1.01); 3.5983 (0.95); 3.5841 (1.01); 3.5704 (2.26); 3.5550 (0.83); 3.5429 (2.36); 3.5146 (1.18); 3.4216 (0.80); 3.3972 (1.87); 3.3691 (0.78); 3.3295 (2.53); 3.3188 (3.16); 3.2921 (1.80); 3.2660 (2.53); 3.2400 (1.75); 3.2143 (0.44); 3.1658 (2.39); 3.1554 (2.78); 3.0945 (1.45); 3.0843 (1.58); 2.9965 (0.81); 2.9859 (0.92); 2.9709 (0.85); 2.9622 (1.30); 2.9534 (1.01); 2.9284 (0.79); 2.9180 (0.85); 2.8956 (0.32); 2.7528 (3.63); 2.7425 (4.09); 2.7241 (3.84); 2.7136 (4.02); 2.6655 (1.86); 2.6549 (2.06); 2.6365 (1.78); 2.6261 (1.83); 2.0260 (16.00); 1.9003 (2.38); 1.8896 (5.18); 1.8789 (2.85); 1.8466 (1.03); 1.8358 (2.11); 1.8255 (1.13); 1.8040 (0.97); 1.7937 (2.02); 1.7835 (1.09); 1.7571 (2.12); 1.7466 (4.21); 1.7360 (2.41); 1.5540 (11.55); 1.4134 (0.99); 1.3886 (0.90); 1.3419 (0.75); 1.3156 (0.74); 1.2598 (0.50); 1.2366 (0.57); 1.1844 (1.92); 1.0994 (0.52); 1.0785 (5.55); 1.0523 (5.50); 0.9865 (11.03); 0.9607 (10.95); 0.9008 (0.59); 0.8333 (0.50); 0.8112 (0.59); 0.7824 (0.57); 0.7502 (0.55); 0.7245 (0.46); 0.6433 (0.34); 0.6177 (0.34)

No. IIa-24, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

9.1652 (0.94); 9.0728 (1.01); 8.9503 (6.07); 8.9477 (5.98); 8.5288 (6.13); 8.5250 (6.03); 3.9453 (1.35); 3.9054 (5.68); 3.5449 (1.73); 3.5325 (1.70); 3.5062 (2.40); 3.4935 (2.26); 3.3867 (0.60); 3.3436 (264.78); 3.3065 (3.05); 3.2849 (2.60); 3.2674 (2.09); 3.2459 (1.91); 3.1667 (0.97); 2.8120 (1.66); 2.6810 (0.39); 2.6769 (0.81); 2.6723 (1.13); 2.6678 (0.85); 2.5426 (0.72); 2.5257 (3.49); 2.5121 (66.26); 2.5078 (134.10); 2.5032 (177.17); 2.4987 (132.59); 2.4943 (67.64); 2.3390 (0.41); 2.3344 (0.84); 2.3300 (1.15); 2.3255 (0.86); 1.3351 (0.36); 1.3158 (15.96); 1.2994 (16.00); 1.2490 (0.33); 1.2342 (0.32); 0.9477 (0.49); 0.9389 (0.89); 0.9174 (6.40); 0.9081 (5.02); 0.8945 (1.34); 0.8853 (0.82); 0.8753 (0.70); 0.8534 (0.52); 0.8376 (0.78); 0.8323 (0.56); 0.8224 (1.44); 0.8071 (4.83); 0.7889 (4.82); 0.7662 (0.83); 0.7508 (0.37); 0.0080 (0.39); −0.0002 (12.25); −0.0085 (0.53)

No. IIa-26, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.8717 (15.40); 8.8694 (15.54); 8.4864 (15.85); 8.4825 (15.76); 8.3229 (0.39); 8.2695 (0.42); 8.0777 (0.43); 7.7065 (0.38); 4.1514 (4.63); 4.1387 (3.79); 3.9052 (16.00); 3.6150 (5.91); 3.6033 (6.10); 3.5730 (8.21); 3.5613 (8.15); 3.3562 (72.65); 3.1669 (6.89); 2.6767 (3.03); 2.6721 (4.09); 2.6677 (3.09); 2.5254 (12.41); 2.5119 (232.26); 2.5076 (463.05); 2.5031 (607.50); 2.4986 (454.95); 2.4944 (234.67); 2.3343 (2.90); 2.3298 (3.98); 2.3253 (2.98); 1.2582 (0.35); 1.2486 (0.52); 1.2353 (0.57); 0.8750 (0.45); 0.0079 (0.73); −0.0002 (20.80); −0.0083 (0.88)

No. IIa-30, Solvent: <[D₆]-DMSO>, Spectrometer: 399.95 MHz

8.8681 (3.65); 8.8491 (0.41); 8.6288 (0.37); 8.4069 (3.72); 8.4024 (3.41); 8.1943 (0.35); 8.1890 (0.35); 7.9500 (0.92); 7.9366 (1.46); 7.9233 (0.80); 5.5399 (0.79); 3.9050 (5.32); 3.7490 (1.58); 3.7358 (1.88); 3.7276 (1.96); 3.7144 (1.76); 3.4459 (0.40); 3.3410 (284.43); 3.2952 (1.33); 3.2820 (1.17); 3.2585 (1.65); 3.2454 (1.60); 3.1740 (1.00); 3.1609 (0.95); 3.1525 (0.32); 3.1282 (0.50); 3.1135 (1.08); 3.1028 (2.50); 3.0955 (2.31); 3.0819 (4.30); 3.0652 (3.50); 3.0508 (2.32); 3.0456 (2.22); 3.0329 (0.97); 3.0182 (0.41); 2.6765 (0.85); 2.6719 (1.15); 2.6673 (0.85); 2.5252 (4.14); 2.5118 (68.50); 2.5074 (134.85); 2.5029 (175.39); 2.4983 (128.97); 2.4939 (64.49); 2.3341 (1.17); 2.3296 (1.48); 2.3251 (1.19); 1.2350 (0.41); 1.0955 (0.63); 1.0853 (0.53); 1.0773 (1.24); 1.0591 (0.66); 1.0381 (0.44); 1.0300 (0.52); 1.0205 (0.63); 1.0059 (7.75); 0.9879 (16.00); 0.9699 (7.79); 0.9536 (1.46); 0.9356 (0.72); 0.9119 (0.48); 0.8940 (0.60); 0.8761 (0.33); −0.0002 (9.34); −0.0084 (0.44)

TABLE E

Compounds of formula (IIb)

(IIb)

embedded image

Reference of synthesis

optical
procedure or phys. chem.

No.
X_n
R¹
R²
R³
R⁴
R⁵
information
data

IIb-1
6-Cl
H
H
COOH
H
H

comm av.

CAS-No. 188916-07-6

IIb-2
5-Cl
H
H
COOH
H
H

comm av.

6-OMe

CAS-No. 1270318-19-8

IIb-3
5-Cl
H
H
COOMe
H
H
—
according to P1

6-OMe

IIb-4
5-Cl
H
H
COOMe
H
H
R-enantiomer
comm av.

6-OMe

CAS-No. 1212838-31-7

IIb-5
5-Cl
H
H
COOMe
H
H
S-enantiomer
comm av.

6-OMe

CAS-No. 1213663-26-3

IIb-6
5-Cl
H
H
COOEt
H
H
—
according to P1

6-OMe

IIb-7
5-Cl
H
H
CONHMe
H
H
—
according to P1

6-OMe

IIb-8
5-Cl
H
H
CONHEt
H
H
—
according to P1

6-OMe

IIb-9
6-Cl
H
H
H
H
H
—
P4

IIb-10
6-CF₃
H
H
H
H
H
—
according to P4

comm av.

CAS-No. 765287-34-1

IIb-11
2-Cl
H
H
H
H
H
—
according to P4

4-Cl

IIb-12
6-Cl
CH₃
H
H
H
H

IIb-13
6-Cl
CH₃
CH₃
H
H
H
—
comm av.

CAS-No. 1060812-06-7

IIb-14
6-CH₃
CH₃
CH₃
H
H
H
—
comm av.

CAS-No. 1060806-41-8

IIb-15
6-OMe
CH₃
CH₃
H
H
H
—
comm av.

CAS-No. 1060807-33-1

IIb-16
6-Cl
F
F
H
H
H
—
comm av.

CAS-No. 1204235-05-1

IIb-17
6-CF₃
H
H
CH₃
H
H
—
comm av.

CAS-No. 910414-32-3

IIb-18
2-Cl
H
H
CH₃
H
H
—
comm av.

CAS-No. 910413-05-7

IIb-19
6-Cl
H
H
CH₃
H
H

comm av.

CAS-No. 910398-62-8

IIb-20
2-OMe
H
H
C₂H₅
H
H
—
comm av.

5-Br

CAS-No. 910407-42-0

IIb-21
6-CF₃
H
H
C₂H₅
H
H
—
comm av.

CAS-No. 910386-05-9

IIb-22
6-Cl
H
H
C₂H₅
H
H
—
comm av.

CAS-No. 910387-17-6

IIb-23
5-CF3
CH₂—CH₂
H
H
H
—
comm av.

CAS-No. 1245915-95-0

IIb-24
6-Cl
CH₂—CH₂
H
H
H
—
comm av.

CAS-No. 1060811-84-8

IIb-25
2-Br
CH₂—CH₂
H
H
H
—
comm av.

CAS-No. 1060811-52-0

IIb-26
4-F
CH₂—CH₂
H
H
H
—
comm av.

CAS-No. 1060809-53-1

IIb-27
6-CF₃
CH₂—CH₂
H
H
H
—
comm av.

CAS-No. 1060811-04-2

IIb-28
6-Br
CH₂—CH₂
H
H
H
—
comm av.

CAS-No. 1060811-50-8

IIb-29
2-OMe
CH₂—CH₂
H
H
H
—
comm av.

CAS-No. 1060807-12-6

IIb-30
4-CH₃
CH₂—CH₂
H
H
H
—
comm av.

CAS-No. 1060804-94-5

IIb-31
5-F
H
(CH₂)₃
H
H

comm av.

CAS-No. 1247729-51-6

IIb-32
5-F
H
(CH₂)₄
H
H

comm av.

CAS-No. 1249152-50-8

IIb-33
5-F
H
(CH₂)₅
H
H

comm av.

CAS-No. 1247860-65-6

IIb-34
4-Cl
H
H
H
H
H

CAS-No. 1393584-52-5

6-CF₃

Synthesis c.f. experimental

part

IIb-35
2-Cl
H
H
H
H
H

Synthesis c.f. experimental

6-CF₃

part

IIb-36
2-Cl
H
H
CH₃
H
H

CAS-No. 1337694-11-7

6-CF₃

TABLE F

Compounds of formula (IIc)

(IIc)

embedded image

Reference of synthesis

procedure or phys. chem.

No.
X_n
R¹
R²
R³
R⁴
R⁵
data

IIc-1
2-F
H
H
H
H
H
P8

3-F

5-F

6-F

IIc-2
2-Me
H
H
H
H
H
according to P8

5-Cl

IIc-3
2-F
H
H
H
H
H
according to P8

5-F

IIc-4
2-F
H
H
COOH
H
H
comm. av.

3-F

CAS-No. 1270314-19-6

5-F

6-F

IIc-5
2-F
H
(CH₂)₄
H
H
according to P5

3-F

5-F

6-F

IIc-6
3-F
H
H
H
H
H
comm av.

5-F

CAS-No. 1314907-15-7

IIc-7
2-CF₃
H
H
H
H
H
comm av.

3-

CAS-No. 1211539-23-9

OMe

IIc-8
2-CF₃
H
H
H
H
H
comm av.

CAS-No. 1060811-11-1

IIc-9
3-Cl
H
H
H
H
H
comm. av.

5-Cl

CAS-No. 910391-44-5

IIc-10
3-Cl
H
H
H
H
H
comm av.

CAS-No. 910410-77-4

IIc-11
2-
H
H
H
H
H
comm av.

OMe

CAS-No. 764708-27-2

IIc-12
2-Me
H
H
H
H
H
comm av.

CAS-No. 625438-03-1

IIc-13
2-Cl
H
H
H
H
H
comm av.

CAS-No. 910388-12-4

IIc-14
3-Cl
H
H
CH₃
H
H
comm av.

5-Cl

CAS-No. 910389-65-0

IIc-15
3-F
H
H
CH₃
H
H
comm av.

5-Fl

CAS-No. 910402-24-3

IIc-16
3-Cl
H
H
CH₃
H
H
comm av.

6-Cl

CAS-No. 910407-17-9

IIc-17
3-F
H
H
CH₃
H
H
comm av.

CAS-No. 910389-92-3

IIc-18
3-Cl
H
H
CH₃
H
H
comm av.

CAS-No. 910389-80-9

IIc-19
2-
CH₃
CH₃
H
H
H
comm av.

OMe

CAS-No. 1060807-35-3

IIc-20
2-
CH₂—CH₂
H
H
H
comm av.

OMe

CAS-No. 1060807-10-4

IIc-21
2-Me
CH₂—CH₂
H
H
H
comm av.

CAS-No. 1060806-23-6

IIc-22
2-CF₃
CH₂—CH₂
H
H
H
comm av.

CAS-No. 1060811-06-4

IIc-23
2-Cl
CH₂—CH₂
H
H
H
comm av.

CAS-No. 1060811-85-9

IIc-24
3-Cl
H
H
COOH
H
H
comm av.

5-Cl

CAS-No. 1270326-34-5

IIc-25
2-Me
CH₃
CH₃
H
H
H
comm av.

CAS-No. 1060806-42-9

IIc-26
2-Cl
CH₃
CH₃
H
H
H
comm av.

CAS-No. 1060812-07-8

EXAMPLES

Abbreviations which are used in the text and in the formulae:

Int=Intermediate

Synthesis of N-{2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-methylpropyl}-2-(trifluoromethyl)benzamide (Ia-93)
Step 1: Synthesis of 2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-methylpropanenitrile (Int-2)

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Under Argon, 20.2 g (0.091 mol) of 3-chloro-5-(trifluoromethyl)pyridin-2-yliacetonitrile (P10, prep. example 7, page 59) were dissolved in 0.1 L of tetrahydrofuran (THF) at 5° C. 350 mL of a 1N solution of potassium 2-methylpropan-2-olate (0.35 mol) in tetrahydrofuran were slowly added to the reaction medium. After 2 h, 42.1 g (0.297 mol) of methyl iodide were added dropwise to the reaction mixture, which was stirred for three days at room temperature. 500 mL of water were added to the reaction mixture. After separation, the aqueous phase was extracted twice with 300 mL of diethyl ether. The organic phase was washed with 300 mL of water, dried over magnesium sulfate, filtered and concentrated in vacuo to yield 20 g of crude product which was chromatographed over silica gel to yield 6.10 g (32%) of 2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]propanenitrile (Int-1) and 5.12 g (22%) of 2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-methylpropanenitrile (Int-2).

(Int-1), Solvent: <CDCl₃>, Spectrometer: 250 MHz

8.8851 (2.85); 8.8810 (2.90); 8.0597 (3.16); 8.0531 (3.03); 7.3468 (0.43); 4.6887 (0.86); 4.6601 (2.73); 4.6314 (2.77); 4.6028 (0.92); 1.9535 (0.37); 1.8201 (16.00); 1.7915 (15.84); 1.6816 (1.04); 1.3985 (0.39); 1.3699 (0.41); 1.3263 (2.32); 0.9654 (0.63); 0.9398 (2.11); 0.9121 (0.74)

(Int-2), Solvent: <CDCl₃>, Spectrometer: 250 MHz

8.8501 (0.70); 8.8470 (0.81); 8.8429 (0.82); 8.8399 (0.72); 8.0975 (0.87); 8.0908 (0.87); 2.7950 (0.75); 1.9777 (16.00); 1.3467 (1.18); 0.9585 (1.01); 0.9309 (0.35)

Step 2: Synthesis of tert-butyl 2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-methylpropyl carbamate (Int-3)

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270 mg of 2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-methylpropanenitrile (Int-2) (1.08 mMol), 470 mg (2.16 mMol) of di-tert-butyl carbonate, 256 mg (1.08 mMol) of nickel-(II)-chloride-hexahydrate were stirred in 7 mL of methanol at room temperature. 284 mg (7.6 mMol) of sodium borohydride were added portionwise. After 2 hours of stirring, 20 mL of ethyl acetate were added to the reaction mixture, followed by 5 mL of an aqueous solution of sodium bicarbonate. After separation, the organic phase was washed with 5 mL of an aqueous solution of sodium bicarbonate, dried over magnesium sulfate, filtered and concentrated to yield 283 mg (48%) of crude material, which was purified over silica gel to produce 185 mg of desired product tert-butyl {2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-methylpropyl}carbamate (Int-3).

(Int-3), Solvent: <CDCl₃>, Spectrometer: 250 MHz

8.6142 (1.38); 7.8087 (1.59); 7.1968 (0.42); 5.3003 (0.41); 3.5212 (2.11); 3.4946 (2.03); 1.6795 (0.65); 1.4510 (3.37); 1.4297 (18.21); 1.3873 (1.28); 1.3387 (16.00); 1.2821 (0.82); 1.1813 (0.64); 1.0122 (0.48)

Step 3: Synthesis of 2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-methylpropan-1-amine hydrochloride (Int-4) (not isolated)

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according to P10, prep. example 7, page 60 and

Step 4: Synthesis of N-{2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-methylpropyl}-2-(trifluoromethyl)benzamide (Ia-93)

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according to P10, e.g. prep. example 2, page 56, in a one-pot reaction

In a similar manner the final products (Ia-94), (Ia-95), (Ia-96), (Ia-97) and (Ia-106) can be prepared.

Synthesis of N-{2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-1-methoxyethyl}-2-(trifluoromethyl)benzamide (Ia-111)
Step 1: Synthesis of N-{2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethylidene}-2-(trifluoromethyl)benzamide (Int-6)

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2.00 g of N-{2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethyl}-2-(trifluoromethyl)benzamide (Int-5), (known from WO 2004/016088), were dissolved in 20 mL of methanol. 1 mL of concentrated bleach was added to the reaction mixture at room temperature. The reaction mixture was stirred for 24 hours at room temperature. 20 mL of a 1N aqueous solution of sodium hydroxide were added to the reaction mixture which was then extracted twice with diethyl ether. The combined organic phases were dried over magnesium sulphate, concentrated in vacuo to yield 1.41 g of crude product which was purified by chromatography on silica gel with ethyl acetate/heptane (3/7 v/v) as eluting phase. 340 mg (17%) of desired N-{2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethylidene}-2-(trifluoromethyl)benzamide (Int-6) were obtained, [M+1]=395.

(Int-6), Solvent: <CDCl₃>, Spectrometer: 250 MHz

8.9332 (9.79); 8.9300 (10.02); 8.1058 (10.17); 8.0994 (10.79); 8.0590 (0.59); 8.0405 (4.14); 8.0293 (4.93); 8.0053 (5.61); 7.8799 (4.19); 7.8553 (5.39); 7.8433 (6.53); 7.8254 (1.03); 7.8135 (0.43); 7.7616 (1.08); 7.7531 (2.30); 7.7313 (7.59); 7.7224 (10.49); 7.7082 (16.00); 7.6941 (8.42); 7.6624 (1.16); 7.3731 (2.26); 6.3219 (5.33); 6.2909 (6.05); 6.2819 (6.18); 6.2509 (5.77); 4.6899 (3.46); 4.6499 (3.13); 4.6312 (10.24); 4.5911 (10.09); 4.5750 (10.55); 4.5440 (10.16); 4.5161 (3.62); 4.4853 (3.08); 4.2001 (0.84); 4.1747 (0.34); 3.9138 (2.48); 3.7663 (0.44); 3.5945 (1.93); 3.5203 (0.71); 2.1563 (1.20); 1.7637 (14.75); 1.3752 (2.57); 1.0440 (0.56); 1.0153 (0.88); 0.9906 (2.20); 0.9629 (0.84)

Step 2: Synthesis of N-{2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-1-methoxyethyl}-2-(trifluoromethyl)benzamide (Ia-111)

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0.16 g of N-{2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethylidene}-2-(trifluoromethyl)benzamide (Int-6) were diluted in 2 mL of methanol. 50 μL of sulfuric acid 99% were added. The reaction mixture was stirred at room temperature for 48 hours. A mixture of dichloromethane (10 mL) and water (5 mL) was added. After separation, the aqueous phase was extracted twice with dichloromethane. The combined organic phases were washed with 5 mL of water, dried over magnesium sulfate, filtered, concentrated to yield to 0.150 g of crude material, which was purified by chromatography on silica gel to yield 0.107 g (63%) of desired product N-{2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-1-methoxyethyl}-2-(trifluoromethyl)benzamide (Ia-111), [M+1]=427.

(Ia-111), Solvent: <CDCl₃>, Spectrometer: 250 MHz

12.1063 (0.36); 12.0712 (1.19); 12.0521 (0.95); 12.0171 (0.38); 11.9822 (0.38); 8.8855 (0.60); 8.1085 (16.00); 7.8954 (0.37); 7.7656 (0.49); 7.2610 (0.36); 6.0372 (0.33); 5.6296 (0.39)

Synthesis of 2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-1-{[2-(trifluoromethyl)benzoyl]amino}ethyl acetate (Ia-112)

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0.16 g of N-{2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethylidene}-2-(trifluoromethyl)benzamide (Int-6) were diluted in 2 mL of acetic acid. The reaction mixture was stirred for two days at room temperature and then heated to 90° C. for one day and left at room temperature for four days. After concentration in vacuo, the crude product was purified by chromatography on silica gel to yield 0.045 g (24%) of desired product 2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-1-{[2-(trifluoromethyl)benzoyl]amino}ethyl acetate (Ia-112), [M+1]=455.

(Ia-112), Solvent: <CDCl₃>, Spectrometer: 250 MHz

8.7470 (0.39); 8.6387 (1.99); 7.9142 (2.37); 7.9078 (2.10); 7.6281 (0.97); 7.6011 (1.38); 7.5952 (1.39); 7.5508 (0.70); 7.5391 (0.62); 7.5255 (1.49); 7.5013 (2.27); 7.4927 (2.11); 7.4625 (1.11); 7.4431 (1.65); 7.4120 (0.74); 7.1939 (0.35); 6.4536 (0.68); 6.2788 (0.95); 6.2616 (1.19); 6.2555 (1.23); 6.2384 (0.96); 4.1809 (0.48); 4.1640 (0.52); 4.1544 (0.51); 4.1375 (0.51); 4.1235 (0.73); 4.1067 (0.74); 4.0970 (0.74); 4.0802 (0.66); 3.8884 (0.67); 3.8658 (1.13); 3.8431 (0.71); 3.8313 (0.54); 3.8084 (0.79); 3.7859 (0.47); 3.4015 (0.59); 2.0705 (16.00); 1.9568 (0.34); 1.1896 (0.99); 0.8053 (0.74); 0.7776 (0.33)

Synthesis of intermediates (IIa-15) and (IIa-14)
Step 1: Preparation of ethyl (3,5-dichloropyridin-2-yl)(difluoro)acetate (Int-7)

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To a solution of 56 g (0.246 mol) of 2-bromo-3,5-dichloropyridine in 500 mL of dry dimethylsulfoxide, were added 53 g (0.261 mol) of ethyl bromodifluoroacetate followed by 94 g (0.518 mol) of copper bronze (200 mesh). The beige suspension was heated at 50° C. for 5 hours. After cooling of the reaction mixture, a solution of 44 g (0.328 mol) of potassium monophosphate in 280 mL of water was added and stirred for 1 hour. The black mixture was then filtered over a cake of Supercel™, and the cake was washed three times by 200 mL of ethyl acetate. The organic phases were collected, washed with brine and dried over magnesium sulfate. Evaporation of the solvent under vacuum gave 57.6 g of brown oil. After purification by column chromatography on silica gel (heptane/ethyl acetate 9/1) 40 g (57%) of ethyl (3,5-dichloropyridin-2-yl)(difluoro)acetate (Int-7) were obtained as a yellow oil, (M+1)=270, ¹⁹F-NMR (235 MHz, CDCl₃) δ (ppm): −104.21 (CF₂).

Preparation of ethyl[3-chloro-5-(trifluoromethyl)pyridin-2-yl](difluoro)acetate (Int-8)

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Under the same conditions, 47 g of 2-bromo-3-chloro-5-(trifluoromethyl)pyridine, yields 46.7 g (46%) of ethyl[3-chloro-5-(trifluoromethyl)pyridin-2-yl](difluoro)acetate (Int-8) as a yellow oil.

Step 2: Preparation of 2-(3,5-dichloropyridin-2-yl)-2,2-difluoroethanol (Int-9)

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To a solution of 10 g (37 mmol) of ethyl (3,5-dichloropyridin-2-yl)(difluoro)acetate (Int-7) in 60 mL of ethanol, were added portionwise at 0° C., 1.05 g (27.7 mmol) of sodium borohydride. The reaction mixture was stirred below 10° C. for 2 hours. 30 mL of 1 N HCl were then slowly added followed by 500 mL of water. The aequeous phase was extracted three times by 300 mL of ethyl acetate and the organic phase was successively washed with brine, water and dried over magnesium sulfate. After evaporation of the solvent under vacuum 8.5 g of yellow oil were obtained. After trituration in diisopropyl ether and filtration 6.8 g (80%) of 2-(3,5-dichloropyridin-2-yl)-2,2-difluoroethanol (Int-9) were obtained as a white solid. Mp (melting point)=56° C. (M+1)=228. ¹⁹F-NMR (235 MHz, CDCl₃) δ (ppm): −105.85 (CF₂).

Preparation of 2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2,2-difluoroethanol (Int-10)

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Under the same conditions, reduction of 12 g of ethyl[3-chloro-5-(trifluoromethyl)pyridin-2-yl](difluoro)acetate (Int-8), resulted in 6.8 g (65%) of 2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2,2-difluoroethanol (Int-10) as a yellow oil, (M+1)=262, ¹⁹F-NMR (235 MHz, CDCl₃) δ (ppm): −106.74 (CF₂); −63.18 (CF₃).

Step 3: Preparation of 2-(3,5-dichloropyridin-2-yl)-2,2-difluoroethanamine (IIa-15)

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To a solution of 1.3 g (5.7 mmol) of 2-(3,5-dichloropyridin-2-yl)-2,2-difluoroethanol (Int-9) in dry acetonitrile under argon, were added 0.744 mL (9.12 mmol) of dry pyridine. The reaction mixture was cooled to 0° C. and 1.06 mL (6.27 mmol) of triflic anhydride were added dropwise in 15 min while maintaining the temperature below 8° C. The reaction mixture was stirred at 0° C. for additional 30 min 9.9 mL of a 28% w/w aqueous solution of ammonia (144 mmol) were added and the reaction mixture was stirred at room temperature for 2 days. The reaction mixture was diluted with 50 mL of brine and the product extracted three times with 25 mL of ethyl acetate. The organic phases were collected, washed three times with 40 mL of brine and dried over magnesium sulfate. Afater evaporation of the solvent under vacuum 1.09 g of brown oil were obtained. After purification by column chromatography on silica gel (heptane/ethyl acetate gradient) 0.65 g (50%) of 2-(3,5-dichloropyridin-2-yl)-2,2-difluoroethanamine (IIa-15) were obtained as a yellow oil, (M+1)=227, ¹⁹F-NMR (235 MHz, CDCl₃) δ (ppm): −104.80 (CF₂).

Preparation of 2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2,2-difluoroethanamine (IIa-14)

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Under the same conditions, amination of 1.5 g of 2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2,2-difluoroethanol (Int-10), produced 0.4 g (27%) of 2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2,2-difluoroethanamine (IIa-14) as a yellow oil, (M+1)=261, ¹⁹F-NMR (235 MHz, CDCl₃) δ (ppm): −105.48 (CF₂); −62.97 (CF₃).

Synthesis of intermediate (IIa-16)
Step 1: Preparation of 3-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]butan-2-one (Int-12)

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6.00 g of 1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]acetone (Int-11) (27 mMol) (synthesis according to P10 and comm av.) and 5.75 g of methyl iodide (40.5 mMol) were diluted in 120 mL of dimethoxyethane. 3.03 g of potassium hydroxide were added portionwise at room temperature. After cooling, 100 mL of water were added to the reaction mixture which was extracted twice with 150 mL of ethyl acetate. The organic phase was washed twice with 100 mL of water, dried over magnesium sulfate and concentrated. After purification on silica, 0.67 g (39%) of desired product 3-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]butan-2-one (Int-12) were obtained, [M+1]=252.

Step 2: Preparation of 3-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]butan-2-amine (IIa-16)

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0.64 g of 1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]butan-2-one (Int-12) (0.0025 mol) were diluted in 5 mL of methanol. 7.0 g of molecular sieves 3 Å, 1.90 g (0.025 mol) of ammonium acetate and 0.39 g (0.0052 mol) of sodium cyanoborohydride were added. The reaction medium was stirred overnight at room temperature. After filtration, the pH was adjusted to 9 with an aqueous solution of 1 N sodium hydroxide. The reaction mixture was concentrated to dryness and 30 mL of ethyl acetate were added. The organic phase was washed with an aqueous solution of 1 N sodium hydroxide, brine and water; dried over magnesium sulfate, filtered and concentrated to dryness. The crude material was dissolved in 15 mL of 1 N hydrochloric acid and extracted with 15 mL of ethyl acetate. An aqueous solution of 1 N sodium hydroxide was added to the aqueous phase, which was subsequently extracted twice with 15 mL of ethyl acetate. The organic phase was dried over magnesium sulfate, filtered and concentrated to dryness. 0.21 g (32%) of desired product 1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]butan-2-amine (IIa-16) were obtained, [M+1]=253.

(IIa-16), Solvent: <CDCl₃>, Spectrometer: 250 MHz

8.8007 (1.26); 8.7474 (4.38); 8.7114 (0.96); 8.6750 (0.36); 7.9494 (0.94); 7.9165 (5.80); 7.8572 (0.64); 7.2852 (4.01); 4.4592 (0.43); 4.4301 (0.35); 3.7320 (3.86); 3.5142 (0.35); 3.4764 (0.56); 3.4505 (1.77); 3.4238 (3.16); 3.3975 (3.05); 3.3807 (1.53); 3.3561 (2.58); 3.3312 (3.03); 3.3063 (1.80); 3.2810 (0.52); 3.0742 (0.39); 3.0493 (0.38); 2.1316 (7.72); 1.6759 (0.81); 1.6137 (16.00); 1.5889 (2.25); 1.5492 (0.55); 1.5133 (1.30); 1.4535 (4.53); 1.3733 (1.83); 1.3369 (13.49); 1.3099 (13.31); 1.2792 (4.17); 1.2534 (4.91); 1.2219 (4.68); 1.1978 (3.94); 1.1754 (0.82); 1.0772 (12.77); 1.0519 (12.76); 0.9908 (1.18); 0.9655 (1.06); 0.9102 (0.50); 0.8863 (0.66); 0.8671 (0.49); 0.7657 (0.94); 0.7408 (0.83)

In a similar manner compound (IIa-24) can be prepared by reacting 1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]acetone (Int-11) and cyclopropylamine.

Synthesis of intermediate (IIa-40)

Preparation according to known methods (cf. J. Amer. Chem. Soc. 72, 2804-6 (1950); WO 1984/03278; WO 2008/06479; THL 45, 7407-08 (2004))

(IIa40), Solvent: <CDCl₃>, Spectrometer: 400 MHz

See FIG. 17

Synthesis of Intermediate (IIa-41)

Preparation according to known methods (cf. J. Amer. Chem. Soc. 72, 2804-6 (1950); WO 1984/03278; WO 2008/06479; THL 45, 7407-08 (2004))

(IIa41), Solvent: <CDCl₃>, Spectrometer: 400 MHz

See FIG. 18

Synthesis of Intermediate (IIb-34)
Step 1: Preparation of 4-chloro-6-(trifluoromethyl)nicotinic acid (Int-11)

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A solution of 2,2,6,6-tetramethylpiperidin (198.8 g, 1.41 mol) in tetrahydrofuran (1.5 L) was added n-butyl-lithium (564 mL, 1.41 mol) dropwise at −78° C. Then the mixture was stirred from −78° C.˜−30° C. for 30 minutes. Then the mixture was cooled to −78° C. and a solution of 6-(trifluoromethyl)nicotinic acid (90 g, 1.47 mol) in tetrahydrofuran (2.5 L) added dropwise at −78° C., then the mixture was stirred from −78° C.-−40° C. for 1 hour. The mixture was cooled to −78° C. and a solution of hexachloroethane (222.5 g, 0.94 mol) was added to the reaction mixture dropwise. The mixture was stirred at −78° C. for 3 hours. Aqueous ammoniumchloride (1500 mL) was added to the mixture slowly at −78° C. and the mixture was stirred at room temperature for 20 minutes. The mixture was extracted with ethyl acetate (1 L*3). The combined organic layer was concentrated and the residue was purified by silica gel chromatography eluted with dichloromethane: methanol=20:1 to yield 4-chloro-6-(trifluoromethyl)nicotinic acid (Int-11) (85 g, 80%) as a brown solid.

(Int-11), Solvent: <CD₃OD>, Spectrometer: 400 MHz

See FIG. 19

Step 2: Preparation of [4-chloro-6-(trifluoromethyl)pyridin-3-yl]methanol (Int-12)

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To a mixture of 4-chloro-6-(trifluoromethyl)nicotinic acid (Int-11) (85 g, 0.377 mol) in tetrahydrofuran (1.5 L) was added BH₃-THF (755 mL, 0.755 mol, 1M in THF) slowly with ice bath. The mixture was stirred at room temperature overnight. Aqueous NH₄Cl (500 mL) was added to the mixture slowly with ice bath and the mixture was poured into water (1 L). The mixture was extracted with Ethyl acetate (1L*3). The combined organic layer was washed with brine, dried over Na₂SO₄and concentrated to give crude[4-chloro-6-(trifluoromethyl)pyridin-3-yl]methanol (Int-12) (90 g, 100%) as brown syrup, which was used for the next step without further purification.

(Int-12), Solvent: <CD₃OD>, Spectrometer: 400 MHz

See FIG. 20

Step 3: Preparation of 4-chloro-5-(chloromethyl)-2-(trifluoromethyl)pyridine (Int-13)

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[4-Chloro-6-(trifluoromethyl)pyridin-3-yl]methanol (Int-12) (90 g, 0.426 mol) was added to SOCl₂(700 mL) slowly with ice bath, the mixture was refluxed for 1 hour. The mixture was concentrated and the residue was poured into water (1 L). The mixture was adjusted to pH=7-8 with solid NaHCO₃. The mixture was extracted with ethyl acetate (500 mL*3). The combined organic layer was concentrated to yield 4-chloro-5-(chloromethyl)-2-(trifluoromethyl)pyridine (Int-13) (80 g, 87%) as brown syrup which was used for the next step without further purification.

(Int-13), Solvent: <CDCl₃>, Spectrometer: 400 MHz

See FIG. 21

Step 4: Preparation of [4-chloro-6-(trifluoromethyl)pyridin-3-yl]acetonitrile (Int-14)

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Trimethylsilylcyanid (TMSCN) (69.3 g, 0.7 mol) was added to a solution of 4-chloro-5-(chloromethyl)-2-(trifluoromethyl)pyridine (Int-13) (80 g, 0.348 mol) and Tetra-n-butylammoniumfluoride (129.5 g, 0.7 mol) in acetonitrile (1.5 L) slowly. Then the mixture was stirred at 20-30° C. for 2 hours. Thin layer chromatography (petroleum ether: EtOAc=3:1) showed all of starting material was consumed. The mixture was concentrated and the residue was purified by silica gel chromatography eluted with petroleum ether: EtOAc=20:1˜3:1 to yield [4-chloro-6-(trifluoromethyl)pyridin-3-yl]acetonitrile (Int-14) (50 g, 60% from NMR, 39% of yield) as yellow syrup.

(Int-14), Solvent: <CDCl₃>, Spectrometer: 400 MHz

See FIG. 22

Step 5: Preparation of 2-[4-chloro-6-(trifluoromethyl)pyridin-3-yl]ethanamine (IIb-34) hydrochloride

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To a mixture of [4-chloro-6-(trifluoromethyl)pyridin-3-yl]acetonitrile (Int-14) (50 g, 0.227 mol) in THF (1.5 L) was added BH₃-THF (908 mL, 0.908 mol, 1N in THF) slowly with ice bath. Then the mixture was stirred at room temperature for 3 hours. Methanol (500 mL) was added to the mixture slowly with ice bath. The mixture was concentrated and the residue was purified by silica gel chromatography eluted with dichloromethane: methanol=20:1˜10:1 to give crude 2-[4-chloro-6-(trifluoromethyl)pyridin-3-yl]ethanamine (IIb-34×HCl) (20 g), which was poured into HCl-ethyl acetate (300 mL) and stirred at room temperature for 1 hour. The mixture was filtered and the filter cake was washed with methyl-t-butylether (20 mL*3) and dried to yield 2-[4-chloro-6-(trifluoromethyl)pyridin-3-yl]ethanamine (IIb-34×HCl) (14 g, 46%, hydrochloride salt) as off-white solid.

(IIb-34×HCl), Solvent: <CD₃OD>, Spectrometer: 400 MHz

See FIG. 23

Synthesis of Intermediate (IIb-35)
Step 1: Preparation of 2-chloro-6-(trifluoromethyl)nicotinic acid (Int-15)

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To a stirred solution of 2-chloro-6-(trifluoromethyl)pyridine (50.0 g, 1.0 eq.) in tetrahydrofuran (1.01) was added drop wise lithium diisopropylamide (LDA) (44.2 g, 1.5 eq.) at −78° C. After 2 h dry carbondioxide (500 g) was added at −78° C. The resulting reaction mixture was allowed to room temperature and stirred for 10 min. The reaction progress was monitored by TLC. After completion of reaction, the reaction mixture was acidified with 1 N HCl up to pH 2 and extracted with ethyl acetate (2×500 mL). The combined organic layer was washed with water (500 mL), brine (500 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to get crude product which was triturated with pet ether to get pure 2-chloro-6-(trifluoromethyl)nicotinic acid (Int-15) (40.0 g, 64.6%).

(Int-15), Solvent: <CDCl₃>, Spectrometer: 400 MHz

See FIG. 24

Step 2: Preparation of [2-chloro-6-(trifluoromethyl)pyridin-3-yl]methanol (Int-16)

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To a stirred solution of e 2-chloro-6-(trifluoromethyl)nicotinic acid (Int-15) (40 g, 1.0 eq.) in THF (400 mL) was added BH₃-THF (266.6 mL, 1.5 eq) at room temperature. The progress of the reaction was monitored by TLC. After 16 h the reaction mixture was concentrated under reduced pressure to remove THF. The resulting reaction mixture was diluted with 10% NaHCO₃(500 mL) and extracted with ethyl acetate (2×500 mL). The combined organic layers were washed with water (500 mL), brine (500 mL), dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure to get crude [2-chloro-6-(trifluoromethyl)pyridin-3-yl]methanol (Int-16) as light yellow liquid, 32 g (85.5%).

(Int-16), Solvent: <CDCl₃>, Spectrometer: 400 MHz

See FIG. 25

Step 3: Preparation of 2-chloro-6-(trifluoromethyl)nicotinaldehyde (Int-17)

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To a stirred solution of [2-chloro-6-(trifluoromethyl)pyridin-3-yl]methanol (Int-16) (80.0 g, 1.0 eq.) in dichloromethane (700 ml) was added pyridinium chlorochromate (160.0 g, 2.0 eq), silicium dioxide (240 g) at room temperature and stirred for 4 h. The progress of the reaction was monitored by TLC. After completion of reaction, reaction mixture was filtered through silica gel bed and washed the bed with excess 90% ethyl acetate in pet ether and filtrate was concentrated under reduced pressure to get crude 2-chloro-6-(trifluoromethyl)nicotinaldehyde (Int-17) as yellow liquid (70.0 g, 88.3%). GC-MS: m/z 209 ([M]).

Step 4: Preparation of 1-[2-chloro-6-(trifluoromethyl)pyridin-3-yl]-2-nitroethanol (Int-18)

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To a stirred solution of 2-chloro-6-(trifluoromethyl)nicotinaldehyde (Int-17) (70 g, 1.0 eq.) in nitro methane (700 mL) was added sodium hydroxide (6.7 g, 0.5 eq.) at room temperature. The resulting reaction mixture was heated to 100° C. and stirred for 2 h. The progress of the reaction was monitored by TLC. After completion of reaction, the reaction mixture was concentrated under reduced pressure to remove nitro methane quenched with ice water (500 mL) and extracted with ethyl acetate (2×1.0 L). The combined organic layer was washed with water (500 mL), brine (500 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to get pure 1-[2-chloro-6-(trifluoromethyl)pyridin-3-yl]-2-nitroethanol (Int-18) (65.0 g, 72.0%).

(Int-18), Solvent: <CDCl₃>, Spectrometer: 400 MHz

See FIG. 26

Step 5: Preparation of 2-chloro-3-[(E)-2-nitrovinyl]-6-(trifluoromethyl)pyridine (Int-19)

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To a stirred solution of 1-[2-chloro-6-(trifluoromethyl)pyridin-3-yl]-2-nitroethanol (Int-18) (27 g, 1.0 eq.) in dichloromethane (270 mL) was added 4-dimethylamino pyridine (13.5 g, 1.1 eq.) followed by drop wise addition of acetic anhydride (13.5 g, 1.3 eq) at 0° C. and stirred for 15 min. The progress of the reaction was monitored by TLC. After completion of reaction, the reaction mixture was quenched with ice water and extracted with dichloromethane (2×200 mL). The combined organic layer was washed with water (200 mL), brine (200 mL), dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure to get crude 2-chloro-3-[(E)-2-nitrovinyl]-6-(trifluoromethyl)pyridine (Int-19) (22.0 g, 87.6%).

(Int-19), Solvent: <CDCl₃>, Spectrometer: 400 MHz

See FIG. 27

Step 5: Preparation of 2-[2-chloro-6-(trifluoromethyl)pyridin-3-yl]ethanamine (IIb-35) hydrochloride

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To a stirred solution of NaBH₄(16.0 g, 4.2 eq.) in tetrahydrofuran (125 mL) was added BF₃etherate (125 mL) at 0° C. The resulting reaction mixture was allowed to room temperature and stirred for 15 min 2-Chloro-3-[(E)-2-nitrovinyl]-6-(trifluoromethyl)pyridine (Int-19) (25.0 g, 1.0 eq) in tetrahydrofuran (125 mL) was added to above reaction mixture at room temperature. The reaction mixture was heated to 70° C. and stirred for 2 h. The resulting reaction mixture was allowed to room temperature and stirred for 16 h. The progress of the reaction was monitored by TLC. After completion of reaction, the reaction mixture was quenched in ice water (200 mL) and extracted with ethyl acetate (3×200 mL). The combined organic layers were washed with water (1×100 mL), brine (1×100 mL), dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure to get crude amine. The amine compound was dissolved in ethanolic HCl (50 mL) and stirred at room temperature for 2.0 h. The reaction mixture was concentrated under reduced pressure to get crude 2-[2-chloro-6-(trifluoromethyl)pyridin-3-yl]ethanamine (IIb-35) hydrochloride (15.0 g, 58.3%).

(IIIb-35×HCl), Solvent: <[D₆]-DMSO>, Spectrometer: 400 MHz

See FIG. 28

BIOLOGICAL EXAMPLES

Meloidogyne Incognita—Test

Solvent: 125.0 parts by weight of acetone

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, and the concentrate is diluted with water to the desired concentration. Vessels are filled with sand, a solution of the active ingredient, a suspension containing eggs and larvae of Meloidogyne incognita and salad seeds. The salad seeds germinate and the seedlings grow. Galls develop in the roots.

After 14 days the nematicidal activity is determined on the basis of the percentage of gall formation. 100% means that no galls were found; 0% means that the number of galls found on the roots of the treated plants was equal to that in untreated control plants.

In this test, for example, the following compounds from the preparation examples showed an activity of 100% at an application rate of 20 ppm: Ia-3, Ia-43, Ia-46, Ia-47, Ia-50, Ia-70, Ia-92, Ia-93, Ia-110, Ia-113, Ia-114, Ia-122, Ia-126, Ia-127, Ia-131, Ia-137, Ia-140, Ia-141, Ia-142, Ia-143, Ia-147, Ia-148, Ia-153, Ia-154, Ia-177, Ic-1, Ic-2, Ic-7.

In this test, for example, the following compounds from the preparation examples showed an activity of 90% at an application rate of 20 ppm: Ia-170, Ia-172, Ia-174, Ia-196, Ia-211, Ia-212, Ib-47, Ib-58, Ic-5.

In this test, for example, the following compounds from the preparation examples showed good activity of 70% at an application rate of 20 ppm: Ib-50, Ib-51.

In this test, for example, the following compounds from the preparation examples showed an activity of 100% at an application rate of 4 ppm: Ic-8.

Cooperia Curticei-Test (COOPCU)

Solvent: dimethyl sulfoxide

To produce a suitable preparation of active compound, 10 mg of active compound are dissolved in 0.5 ml solvent, and the concentrate is diluted with “Ringer's solution” to the desired concentration.

Approximately 40 Cooperia curticei larvae are transferred into a test tube containing compound solution. After 5 days percentage of larval mortality are recorded. 100% efficacy means all larvae are killed; 0% efficacy means no larvae are killed.

In this test for example, the following compounds from the preparation examples showed good activity of 100% at an application rate of 100 ppm: Ia-1, Ia-4, Ia-5, Ia-6, Ia-48, Ib-47, Ib-49, Ib-50, Ib-51, Ib-52, Ic-1, Ic-7.

In this test for example, the following compounds from the preparation examples showed good activity of 90% at an application rate of 100 ppm: Ib-48, Ic-59, Ic-60, Ic-75.

In this test for example, the following compounds from the preparation examples showed good activity of 80% at an application rate of 100 ppm: Ic-26, Ic-58.

Haemonchus contortus—Test (HAEMCO)

Solvent: dimethyl sulfoxide

Approximately 40 Haemonchus contortus larvae are transferred into a test tube containing compound solution. After 5 days percentage of larval mortality are recorded. 100% efficacy means all larvae are killed, 0% efficacy means no larvae are killed.

In this test for example, the following compounds from the preparation examples showed good activity of 100% at an application rate of 100 ppm: Ib-47, Ib-49, Ib-50, Ic-1, Ic-7.

In this test for example, the following compounds from the preparation examples showed good activity of 90% at an application rate of 100 ppm: Ia-1, Ib-48, Ib-51.

In this test for example, the following compounds from the preparation examples showed good activity of 80% at an application rate of 100 ppm: Ia-5, Ia-6, Ia-48.

In this test for example, the following compounds from the preparation examples showed good activity of 80% at an application rate of 20 ppm: Ib-52.

Number	Date	Country	Kind
11187507	Nov 2011	EP	regional
11194886	Dec 2011	EP	regional

Number	Name	Date	Kind
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8815772	Bereznak et al.	Aug 2014	B2
20080103049	Witschel et al.	May 2008	A1
20090036311	Witschel et al.	Feb 2009	A1
20100105663	Siegel et al.	Apr 2010	A1

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2004016088	Feb 2004	WO
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2006122952	Nov 2006	WO
2006122955	Nov 2006	WO
2007060409	May 2007	WO
2008006479	Jan 2008	WO
2010145788	Dec 2010	WO
2012118139	Sep 2012	WO

Compounds with nematicidal activity

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Abstract

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CROSS REFERENCE TO RELATED APPLICATIONS

PCT Information

US Referenced Citations (5)

Foreign Referenced Citations (31)

Non-Patent Literature Citations (8)

Related Publications (1)

Provisional Applications (1)

Entry
European Search Report dated Oct. 5, 2012, issued in counterpart European Application No. 11194886.5.
European Search Report dated Feb. 16, 2012, issued in counterpart European Application No. 11187507.6.
International Search Report dated Nov. 2, 2011, issued in counterpart International Application No. PCT/EP2012/071385.
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