SK119695A3 - Imono-substituted phenylacetic acid amides, their preparation and fungicides containing them - Google Patents

Abstract

Described are compounds of the formula (I) in which Y is oxygen or an NR6 group; Z<1> and Z<2> are hydrogen, halogen, alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, haloalkyl, haloalkoxy, haloalkenyloxy, cyano or nitro; R<1> is hydrogen, alkyl, haloalkyl or aryl; R<2> is hydrogen, alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkenyl, aryl, heteroaryl, arylalkyl, heteroarylalkyl, arylalkenyl, heteroarylalkenyl, aryloxyalkyl, heteroarylalkyl, arylalkenyl, heteroarylalkenyl, aryloxyalkyl, heteroaryloxyalkyl, acyl, arylcarbonyl, heteroarylcarbonyl or alkoxycarbonyl and R<3>, R<4>, R<5> and R<6> are hydrogen or alkyl, whereby R<6> and R<2> can together form a ring. Also described are fungicides containing these compounds.

Description

Disclosed are compounds of formula I, wherein Y is oxygen or a group NR ^6, Z ¹ and Z ² are H, halogen, alkylene, alkyl, alkynyl, alkoxy, alkenyloxy, haloalkyl, haloalkoxy, -halogenoalkenyloxy, cyano or nitro, R ¹ represents hydrogen, alkyl, haloalkyl or aryl, R ² represents hydrogen, alkyl, alkenyl, alkynyl cycloalkyl, cycloalkenyl, aryl, heteroaryl, aralkyl, heteroarylalkyl, heteroarylalkyl, heteroarylalkynyloxy, arylalkenyl, arylalkenyl, arylalkenyl, arylalkenyl, arylalkenyl, arylalkenyl; heteroarylcarbonyl or alkoxycarbonyl, R ³ , R ⁴ , R ⁵ and R ⁶ represent a hydrogen atom or an alkyl group, as well as R ⁶ and R ² together may be a ring, and the fungicidal compositions containing these compounds.

γι / MC-q <r

Iminosubstituted phenylacetic acid amides, process for their preparation and fungicidal compositions containing them

Technical field

The present invention relates to substituted phenylacetic acid amides of formula I

wherein the substituents have the following meanings:

Y is oxygen or a group NR ^6. ,,. _x

Z and Z are each independently hydrogen, halogen, alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, haloalkyl haloalkoxy, haloalkenyloxy, cyano or nitro,

Zanmená ^R1 is H, alkyl, haloalkyl or aryl,

R ² represents a hydrogen atom or an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heteroarylalkyl, heterocyclyl, cylcoalkenyl, aralkyl, aryl, heteroaryl, arylalkenyloxy, heteroarylalkenyloxy, heteroarylalkenyl, heteroarylalkenyl, heteroarylalkenyl, heteroarylalkenyl , acyl, arylcarbonyl, heteroarylcarbonyl or alkoxycarbonyl,

R ³ , R ⁴ , R ⁵ and R ⁶ are each independently hydrogen or alkyl or

R ⁶ and R ² together with q of the nitrogen atom of which they are substituents may be a ring.

The invention further relates to a process for the preparation of these compounds and intermediates which are required for the preparation of these compounds.

BACKGROUND OF THE INVENTION

It is known that iminosubstituované phenylacetic acid derivatives ¹ are used as antifungal agents (Patent no. 499,823). However, their effect is in many cases unsatisfactory.

SUMMARY OF THE INVENTION

Accordingly, it is an object of the present invention to provide compounds with improved activity and improved spectrum of activity.

For this purpose, the compounds of the general formula I defined above have been found.

!

!

In addition, it has been found that the compounds of formula I have good insecticidal, nematicidal and acaricidal activity. A fungicidal effect is preferred.

With respect to biological activity in controlling harmful fungi, the compounds of the formula I in which the substituents have, for example, the following meanings are suitable:

Z and Z are hydrogen, halogen, such as flora, chloro, bromo and iodo, or, for example, methyl, methoxy, cyano and nitro,

R ³ , R ⁴ , R ⁵ and R ⁶ represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-di methylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl,

1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl,

4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl,

1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethyl propyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl,

R ¹ represents a hydrogen atom, x ¹ is a C 1 -C 4 alkyl group such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl and

1,1-dimethylethyl, C 1 -C 4 haloalkyl, in particular C 1 or C 2 haloalkyl, such as chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, chlorodifluoromethyl, chlorodifluoromethyl, chlorodifluoromethyl, chlorodifluoromethyl, chlorodifluoromethyl, chlorodifluoromethyl fluoroethyl, 2,2-difluoroethyl,

2,2,2-trifluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl, optionally substituted aryl, such as phenyl, naphthyl and anthryl, preferably phenyl and naphthyl, especially phenyl, n

R ' ¹ represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms as mentioned above, an optionally substituted alkenyl group having 3 to 15 carbon atoms, in particular an alkyenyl group having 3 to 6 carbon atoms such as 2-propenyl, 2-butenyl , 3-butenyl, 1-methyl-2-propenyl,

2-methyl-2-propenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3- butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-2-propenyl, 2-

-hexenyl, 3-hexenyl,

2-methyl-2-pentenyl; 1-methyl-3-pentenyl, 4-methyl-3-pentenyl,

3-Methyl-4-pentenyl

1,1-dimethyl-3-butenyl, nyl,

4-hexenyl, 5-hexenyl,

3-methyl-2-pentenyl,

2-methyl-3-pentenyl, 1-methyl-4-pentenyl,

4-methyl-4-pentenyl,

1,2-dimethyl-2-butenyl,

1-Methyl-2-pentenyl

4-methyl-2-pentenyl,

3-methyl-3-pentenyl,

2-Methyl-4-pentenyl

1, l-dimethyl-2-butenyl,

1,2-dimethyl-3-bute2,2-dimethyl-1,3-dimethyl-2-butenyl,

1,3-dimethyl-3-butenyl,

3-butenyl,

2,3-dimethyl-2-butenyl,

2,3-dimethyl-3-butenyl,

3,3-dimethyl-2-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl,

2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, N, 1-ethyl-1-methyl-2-propenyl and 1-ethyl-2-methyl -2-propenyl, optionally substituted C 3 -C 8 alkynyl such as 2-propynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl,

2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl,

2-methyl-3-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl,

1-Methyl-2-pentynyl

2-Methyl-3-pentynyl

2-hexinyl, 3-hexinyl,

1-Methyl-3-pentynyl

2-Methyl-4-pentynyl

4-hexinyl, 5-hexinyl, 1-methyl-4-pentynyl,

3-methyl-4-pentynyl,

4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl, optionally substituted C 3 -C 8 cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl C1-C4alkoxycarbonylalkyl, both in the alkoxy and alkyl moieties, such as methoxycarbonylmethyl, ethoxycarbonylmethyl, propoxycarbonylmethyl, 1-methylethoxycarbonylmethyl, butoxycarbonylmethyl, 1-methylpropoxycarbonylmethyl, and

1,1-dimethyl and 1,1-dimethylethoxycarbonylmethyl, optionally substituted C 5 -C 8 cycloalkenyl, such as cyclopent-1-enyl, cyclopent-2-enyl, cyclopent-3-enyl, cyclohex-1-enyl, cyclohex- 2-enyl, cyclohex-3-enyl, cyclohept-1-enyl, cyclohept-2-enyl, cyclohept-2-enyl, cyclohept-3-enyl, cyclohept-4-enyl, cyclooct-1-enyl, cyclooct-2- eijiyl and cyclooct-3-enyl, optionally substituted aryl, for example phenyl, naphthyl and anthryl;

an optionally substituted (C 1 -C 4) aralkyl group such as benzyl, 1-phenethyl, 2-phenethyl,

1-phenylpropyl, 2-phenylpropyl, 3-phenylpropyl, 2-methyl-3-phenylpropyl, _A 2-methyl-2-phenylpropyl, 4-phenylbutyl, v

an optionally substituted acyl group, for example a C 1 -C 4 alkylcarbonyl group such as acetyl, propionyl, butyryl, phenyloacetyl and chloroacetyl, an optionally substituted arylcarbonyl group such as benzoyl and 2,4-dichlorobenzoyl, optionally substituted heteroarylcarbonyl such as

2-pyridylcarbonyl;

optionally substituted arylalkenyl having 1 to 4 carbon atoms in the alkenyl moiety, for example phenyl-1-ethenyl, 2-phenyl-1-propenyl, 2,2-diphenyletenyl, 1-phenyl-1-propen-2-yl and 1-phenylbutenyl optionally substituted aryloxyalkyl having 1 to 4 carbon atoms in the alkyl moiety such as phenoxymethyl, phenoxyethyl and phenoxypropyl, optionally substituted heteroaryl, for example 2-pyridyl, 3-pyridyl, 4-pyridyl, 3-pyridazinyl, 4-pyridazinyl, 1- pyrazolyl, 3-pyrazolyl, 4-pyrazolyl, 2-pyrazinyl, 2-pyrimidyl, 4-pyrimidyl, 5-pyrimidyl, 1-indazolyl, 3-indazolyl, 2-furyl, 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 2-thiophenyl, 3-thiophenyl,

1-imidazolyl, 2-imidazolyl, 4-imidazolyl, 5-imidazolyl,

2-isoindolyl, 1-indolyl, 1-indazolyl, 1,2-benzothiazol-3-yl,

1,3-benzothiazol-2-yl, (3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl),

3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 1,2-benzoxazol-3-yl,

1,3-benzoxazol-2-yl, 1,2,4-triazolyl, 1,3,4-triazolyl, 7-pyrinyl, 2-quinolyl, 3-quinolyl, 4-quinolyl, 1-isoquinolyl, 3-isoquinolyl,

4-isoquinolyl, 2-benzofuranyl, 3-benzofuranyl, 1-isobenzofuranyl, 1,2,4-triazin-3-yl and 1,3,5-triazin-2-yl, optionally substituted C 1 -C 4 heteroarylalkyl , such as 2-pyridylmethyl and 3-pyridylmethyl,

An optionally substituted C 2 -C 4 heteroarylalkenyl group, for example 2'-furyl-2-ethenyl, 2'-thienyl-2-ethenyl, 3'-pyridyl-2-ethenyl, optionally substituted heterocyclyl, for example oxiranyl, 1-aziridinyl, 1-azetidinyl, 1-pyrrolidinyl, 2-tetrahydrofuranyl, 2-tetrahydropyranyl, 3-tetrahydropyranyl, 1-piperidinyl, 1-morpholinyl, 1-piperazinyl, 1,3-dioxanyl and 3-tetrahydrothiopyranyl.

and

Groups marked with the term optionally substituted contain, for example, the following radicals in addition to hydrogen atoms:

a halogen atom such as fluorine, chlorine, bromine and iodine, an alkyl group having 1 to 6 carbon atoms such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl,

1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl,

2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl,

1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl,

4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1, 1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl, alkoxy of 1 to 6 carbon atoms such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy, pentoxy, 1-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy,

2.2-dimethylpropoxy, 1-ethyl-propoxy, hexyloxy, 1-methylpentyloxy, 2-methylpentyloxy,

3-methylpentyloxy, 4-methylpentyloxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 1-ethylbutoxy, 1-dimethylbutoxy, etylbutoxyskupinu.

1,1.2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and 1-ethyl-2-methylpropoxy, (C 1 -C 6) alkylthio such as methylthio, ethylthio, propylthio, butylthio methylpropylthio, pin, 1,1-dimethylethylthio,

1-metyletyltioskupinu,

2-metylpropyltioskupentyltioskupinu,

1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio, thio-lpentylthio

3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio,

2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio and 1-ethyl-2-methylpropylthio, haloalkyl of 1 to 4 carbon atoms, especially haloalkyl of 1 or 2 carbon atoms such as chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorofluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl,

2.2.2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl,

2.2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl, haloalkoxy of 1 to 4 carbon atoms, in particular haloalkoxy of 1 or 2 carbon atoms such as chloromethoxy, dichloromethoxy, trifluoromethoxy, fluoromethoxy, fluoromethoxy, fluoromethoxy, fluoromethoxy, fluoromethoxy, fluoromethoxy, fluoromethoxy, fluoromethoxy, fluoromethoxy, , dichlorofluoromethoxy, chloridluoromethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, -2-fluoroethoxy, 2,2,2-trichloroethoxy and pentafluoroethoxy, n-v, C 2 -C 6 alkenyloxy, such as ethenyloxy, 1-propenyloxy, 2-propenyloxy,

1-methyletenyloxy, 1-butenyloxy, 2-butenyloxy, 3-butenyloxy, 1-methyl-1-propenyloxy,

2-methyl-1-propenyloxy, 1-methyl-2-propenyloxy,

2-methyl-2-propenyloxy, 1-pentenyloxy, 2-pentenyloxy, 3-pentenyloxy, 4-pentenyloxy, 1-methyl-1-butenyloxy, 2-methyl-1-butenyloxy, 3-methyl-1-butenyloxy, 1-methyl-2-butenyloxy, 2-methyl-2-butenyloxy, 3-methyl-2-butenyloxy, 1-methyl-3-butenyloxy, 2-methyl-3-butenyloxy, 3-methyl-3-butenyloxy, 1, 1-dimethyl-2-propenyloxy, 1,2-dimethyl-1-propenyloxy, 1,2-dimethyl-2-propenyloxy, 1-ethyl-1-propenyloxy, 1-ethyl-2-propenyloxy, 1-hexenyloxy, 2- hexenyloxy, 3-hexenyloxy, 4-hexenyloxy,

1-methyl-1-pentenyloxy, 2-methyl-1-pentenyloxy,

3-methyl-1-pentenloxy, 4-methyl-1-pentenyloxy, 1-methyl-2-pentenyloxy, 2-methyl-2-pentenyloxy, 3-methyl-

2-pentenyloxy, 4-methyl-2-pentenyloxy, 1-methyl-3-pentenyloxy, 2-methyl-3-pentenyloxy, 3-methyl-3-pentenyloxy, 4-methyl-3-pentenyloxy, 1-methyl-4-pentenyloxy , 2-methyl-4-pentenyloxy, 3-methyl-4-pentenyloxy, 4-methyl-4-pentenyloxy, 1,1-dimethyl-2-butenyloxy, 1,1-dimethyl-3-butenyloxy, cyano, cyano, thiocyanato , nitro, amino, hydroxy, carboxyl, dialkylamino of 1 to 6 atoms in each alkyl moiety, especially dialkylamino of 1 to 4 atoms in each alkyl moiety such as N, N-dimethylamino,

N, N-diethylamino, Ν, Ν-dipropylamino, N, N-di- (1-methylethyl) amino, Ν, Ν-dibutylamino, N, N-di- (1-methylpropyl) amino, N, N- di- (2-metylpropy1) amino,

N, N-di- (1,1-dimethylethyl) amino, N-ethyl-N-methylamino, N-methyl-N-propylamino, N-methyl-N- (1-methylethyl) amino'λ.

N-butyl, N-butyl-N-methylamino, N-methyl-N- (1-methylpropyl) amino, N-methyl-N- (2-methylpropyl) amino, N- (1,1-dimethylethyl) -N-methylamino , N-ethyl-N-propylamino,

N-ethyl-N- (1-methylethyl) amino, N-butyl-N-ethylamino, N-ethyl-N- (1-methylpropyl) amino, N-ethyl-N- (2-methylpropyl) amino, N- ( 1-methylpropyl) -N-propylamino, N- (2-methylpropyl) -N-propylamino, N- (1,1-dimethylethyl) -N-propylamino, N-butyl-N- (1-methylethyl) amino, N- (1-methylethyl) -N- (1-methylpropyl) amino, N- (1-methylethyl) -N- (2-methylpropyl) amino, N- (1,1-dimethylethyl) -N- (1-methylethyl) ) -amino, N-butyl-N- (1-methylpropyl) amino, N-butyl-N- (2-methylpropyl) amino, N-butyl-N- (1,1-dimethylethyl) amino, N- ( 1-methylpropyl) -N- (2-methylpropyl) amino, N- (1,1-dimethylethyl) -N- (1-methylpropyl) amino and N- (1,1-dimethyl-ethyl) -N (2 (methylpropyl) amino, phenyl, phenoxy, phenylthio and phenylamino, which themselves may carry up to 5 halogen atoms as mentioned above and / or 1 to 5 alkoxy groups and 1 to 6 carbon atoms as above, and / or 1 to 1 5 alkylthio groups having 1 to 6 carbon atoms; and / or 1 to 5 haloalkyl groups having 1 to 4 carbon atoms as mentioned above;

and / or 1 to 4 alkoxyiminomethyl groups having 1 to 6 carbon atoms in the alkoxy moiety, such as methoxyiminomethyl, ethoxyiminomethyl, n-propoxyiminomethyl, n-butoxyiminomethyl, n-pentoxyiminomethyl, n-hexyloxyiminomethyl, allyloxyiminomethyl, benzyloxyiminomethyl, isopropoxyutoomethyl, isopropoxyutoomethyl tert-butoxyiminomethyl, and / or 1 to 4 alkoxyiminoethyl groups having 1 to 6 carbon atoms, such as methoxyiminoethyl, ethoxyimino-1-ethyl, n-propoxyimino-1-ethyl, n-butoxyimino-1-ethyl, n-pentyloxyimino- 1-ethyl, n-hexyloxyimino-1-ethyl, allyloxyimino-1-ethyl, benzyloxyimino-1-ethyl, and / or phenyl, phenoxy and benzyloxy, and / or (C 1 -C 4) alkyliminomethyl, such as methyliminomethyl and ethyliminomethyl , and / or 1 to 4 cycloalkyl groups having 3 to 6 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

The novel compounds of formula (I) may be produced in the manufacture by virtue of the double bond -C = C- or -C = N- as an E / Z-isomeric mixture. These mixtures can be separated in the usual way by crystallization or by chromatography by individual components.

Both the individual isomeric compounds and mixtures thereof are included in the invention and can be used as fungicidal agents.

Particularly preferred are compounds of formula I in which

Y is oxygen or a group NR ^6,

I

Z ¹ and Z ² are each independently hydrogen, methyl, methoxy, chlorine or bromine, or trifluoromethyl,

R ¹ is hydrogen, methyl or trifluoromethyl, d

n _x

R represents a hydrogen atom or an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, aralkyl, heteroarylalkyl, aryloxyalkyl or heteroaryloxyalkyl group and

R ^3, R ^4, R ⁵ and R ⁶ are H, methyl or ethyl.

In addition, compounds of the formula I in which

Y is an oxygen atom,

Z and Z2 represent a hydrogen atom;

R ³ and R ⁴ are methyl,

E

R represents a hydrogen atom and in which

R ¹ is hydrogen or methyl;

R ² is H, alkyl, allyl, propargyl, aralkyl, heteroarylalkyl, aryloxyalkyl and heteroaryloxyalkyl.

Further preferred are compounds of formula I wherein

R * represents a hydrogen atom and I

R ² is (3-trifluoromethyl) benzyl.

In addition, compounds of the formula I in which

R @ 1 represents methyl and

, .Γ.

ABOUT '

R is (3-trifluoromethyl) benzyl.

The preparation of the compounds of the formula I according to claim 1 is carried out, for example, as described in Scheme 1 (Z ¹ and Z ² are hydrogen).

(VII)

scheme

Compounds of formula I can be prepared, for example, from esters of formula II (their preparation is known from European Patent Specification No. 499 823) by reacting a compound of formula II with ammonia or an amine of formula III.

Compounds of formula I in which R ⁴ is hydrogen can be produced when the carbonyl compound of formula IV (for its preparation see European Patent Specification No. 393,428, when R ¹ represents a hydrogen atom, and European Patent Publication No. . 499 823, where R ¹ is other than a hydrogen atom) is reacted with the mono alkyl amine of formula V to the cyclic poloaminal of formula VI, which is in equilibrium with its aldehyde form and the keto form of formula VII with a hydroxylamine or a hydrazine derivative of formula VIII or an acid addition salt thereof such as a carbonyl compound of formula VII to give compounds of formula I (with R ⁴ representing alkyl and R ⁵ representing hydrogen).

Intermediates of formula VI or formula VII may be prepared from a compound of formula X (Scheme 2) (which is available in a manner known per se from phenylglyoxylic esters, by reaction with alkoxyamine hydrochloride and monoalkylamine) when the compound of formula X is metallized twice (to a compound of formula XI), which is suitable for alkyls such as butyllithium (J. Org. Chem. 29, 853 (1964)) or a metal amide derivative such as magnesium diisopropylamide (European Patent No. 418 013), and the compound of the formula XI is reacted with a carboxylic acid derivative of the formula XII, for example a carboxylic acid chloride, anhydride or ester, or the compound of the formula XI is converted with an aldehyde of the formula XIII to a carbinol of the formula XIV which is ultimately oxidized to a carbonyl compound of formula VII (al or a cyclic form of formula (VI).

Scheme 2

1) H ₂ NOR ³ x HX

2) H ₂ NR ⁴ *

RM (M = Li), or M (NR _{2) 2} (M = Mg)

The hydroxylamine derivatives of formula VII (Y = O) are either known compounds or can be prepared by known methods, analogously to Houben-Weyl, Vol. X / l, p. 1192 and 1183.

The hydrazine derivatives of the general formula VIII (Y = NR ⁶ ) are either known compounds or can also be prepared according to known methods, analogously to Houben-Weyl, vol. X / 2, p. 271, 280 and 740.

Amines (III and V), phenylglyoxylic acid esters (IX), carboxylic acid derivatives (XII) and aldehydes (XIII) are generally known.

DETAILED DESCRIPTION OF THE INVENTION

The following regulations and examples are intended to clarify the production of new active substances and intermediates.

Example 1

a) Preparation of l-hydroxy-2-methyl-4-metyloxyimino-l, 2,3,4-tetrahydroisoquinoline-3-one (compound of formula VI in Scheme 1, R ^{1 =} H, R ³ = R ⁴ = CH ₃ )

11.0 g (50 mmol) of an aldehyde of general formula IV [(R ^{1 =} H, R ³ = R ⁷ = CH ₃ ), see European patent specification no. 393,428] was dissolved in 200 mL of tetrahydrofuran and stirred with 10 mL of a 40% (112 mmol) aqueous solution of methylamine at 25 ° C for 30 minutes. The resulting compound of formula VI is partially precipitated, the precipitate is filtered off with suction, washed with ether and dried. Additional product is obtained by evaporation of the mother liquors, triturating the residue with di-propyl ether and suction. Colorless crystals having a melting point of 116-168 ° C are obtained. Yield: 9.0 g (82% of theory).

NMR (CDCl3, D-scale): 2.2-2.5 broad signal, OH),

3.26 (s, 3H, NCH ₃ ), 4.06 (s, 3H, OCH ₃ ), 5.71 (s, 1H, CH-OH), 7.2

7.5 (m, 3H), and 8.41 (dd, 1H, aromatic protons) ppm.

¹³ C-NMR (CDCl ₃ , D-scale): 33.0 (q NCH ₃ ), 64.0 (q, OCH ₃ ),

82.6 (d, HC-OH), 125.0 (s, CC = N), 127.6 / 128.7 / 130.2 / 130.6 (4d, tertiary aromatic C), 135.6 (s) (C-CHOH), 141.6 (s, C-N),

161.4 (s, C = O) ppm.

IR (KBr, ν): 3295, 1648, 1576, 1021, 765 cm ^-1 .

b) Preparation monometylamidu 2- (0-3-brómbenzyloximinoetyl) -α-methoxyiminophenylacetic (compound no. 58 in Table 1) and / ⁷ 9 (7.7 mmol) hemiaminal of formula VI, as prepared under a), boil with 2.3 g (7.7 mmol) of 3-bromobenzyloxyamine hydrochloride of formula VIII (R ² -Y = S-BrCl 4 H 2 Cl 2 -O) in

150 ml of tetrahydrofuran for one hour under reflux. After cooling, the reaction mixture was washed twice with brine, dried over magnesium sulfate and evaporated. The remaining oil is chromatographed on silica gel with cyclohexane / ethyl acetate (90:10 to 70:30) and the oily product is crystallized by trituration with diisopropyl ether. Almost colorless crystals are obtained having a melting point of 103-105 ° C. Yield: 1.1 g (38% of theory).

¹ H NMR (CDCl ₃ , D-scale): 2.88 (d, 3H, NCH ₃ ), 3.90 (s,

3H, OCH ₃ ) 5.10 (s, 2H, 0 '), 6.73 (broad 2, 1H, NH), 7.1-7.8 (m, 8H, aromatic protons), 7.94 (s, 1H, CH = NO) ppm.

Example 2

2- (0-3-Methylbenzyloximinomethyl) -α-methoxyiminophenylacetic acid monomethylamide (Compound No. 36 in Table 1)

13.6 g (40 mmol) of methyl 2- (O-3-methylbenzyloximinomethyl) -α-methoxyiminophenyl ester (see European Patent Specification 499 823 for its preparation) are dissolved in 100 ml of tetrahydrofuran and 12 ml of a 40% aqueous solution are added. (150 mmol) of methylamine and the mixture was stirred at 40 ° C for 7 hours.

The mixture was allowed to cool to 25 ° C, diethyl ether was added to the mixture, the phases were separated, the organic phase was washed with water, dried over sodium sulfate and evaporated under reduced pressure. A yellowish oil is obtained. Yield: 13.0 g (96% of theory).

IR (film, V): 1669, 1527, 1411, 1035, 980, 785, 756 cm ^-1 .

Examples of the preparation of the active substances obtainable by the process described are given in the following tables.

Table 1

21ouč.

number R ²

Physical parameters [tt ('C), IR (cm ^-1 ), NMR (ppm)]

1 H 2 ch ₃ tt 99 ⁰ 3 ch ₃ ch ₂ 4 ch ₂ ch ₂ ch ₂ 5 ch ₂ = ch-ch ₂ 6 CH ₂ = C (C1) -CH ₂ NMR (.delta.) = 2.94 (d, 3H)

(s, 3H), 4.68 (S, 2H), 5.43 (d, 2H), 6.8 (s, 1H), 7.2-8.0 (m, 5H)

7 ch ₃ - ch = ch (ch ₃ ) 8 ch ₂ = c (ch ₃ ) -ch ₂ 9 hc = c-ch ₂ 10 ch ₃ -o-ch ₂ -ch ₂ 11 c ₂ h ₅ -o-ch ₂ -ch ₂ 12 ci-ch ₂ -ch ₂ 13 cyclo-C ₃ H ₅ -CH ₂ 14 CH _{3 -CH-CH-CH2} 15 ch ₂ = ch-ch ₂ -ch ₂ 16 ch ₃ —c = c — ch ₂ 17 CH ₃ CH ₂ -CsC-CH ₂ 18 CH ₃ - (CH ₂ ) ₃ 19 CH ₃ - (CH ₂ ) ₄ 20 (CH ₃ ) ₃ C ₅ mp 94 ° C 21 cyclo-CgH ₃₁

Table 1 - continued.

Zlouč. Physical parameters Number R ² [tt (C), IR (cm ^-1 ), NMR (ppm)]

22 2-CH ₃ -cyclo-C ₆ H ₁₀ 23 ^C 6 ^H 5 ^-CH 2 mp Mp 116-119 ° C 24 2-FC ₆ H ₄ -CH ₂ 25 3-FC ₆ H ₄ -CH ₂ 26 4-FC ₆ H ₄ -CH ₂ 27 2-Cl-C ₆ H ₄ CH ₂ 28 3-Cl-C ₆ H ₄ CH ₂ ID: 1667, 1527, 1028, 978, 787, 700 29 4-Cl-C ₆ H ₄ CH ₂ mp 142 ° C 30 2,3-Cl ₂ -C ₆ H ₃ -CH ₂ 31 2,4-Cl ₂ -C ₆ H ₃ -CH ₂ 32 ³ ' ⁵ -Cl ₂ -C ₆ ^H 3 ^-CH 2 mp 92 C 33 2,6-Cl ₂ -C ₆ H ₃ -CH ₂ 34 3,4-Cl ₂ -C ₆ H ₃ -CH ₂ NMR: 2.9 (d, 3H), 3.93 (s, 5.1 (s, 2H); 6.8 (s, 2H) a 7.2 - 8.0 (m, 3H) 35 2-CH ₃ -C ₆ H ₄ -CH ₂ ID: 1667, 1526, 1036, 980, 747 36 3-CH ₃ ^-C 6 ^H ₄ ^-CH 2 ID: 1669, 1527, 1411, 1035, 980, 785, 756 37th 4-CH ₃ -C ₆ H ₄ -CH ₂ IR: 1661, 1522, 1492, 1087, 1035 38 2,3- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ 39 2,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ 40 2,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ 41 3,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ 42 3,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ 43 4,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ 44 2,3,4- (CH ₃ ) ₃ -C ₆ H ₂ -CH ₂ 45 2,4,5- (CH ₃ ) ₃ -C ₆ H ₂ -CH ₂

Table 1 - continued

Zlouč. Physical parameters number R ² [tt ('C), IR (cm ^-1 ), NMR (ppm)]

46 2,4,6- (CH ₃ ) ₃ -C ₆ H ₂ -CH ₂ 47 2,3,6- (CH ₃ ) ₃ -C ₆ H ₂ -CH ₂ I 48 2-CF ₃ ^-C 6 ^H 4 ^-CH 2 49 ³ - ^CF 3 ^C 6 ^H 4 - ^CH 2 1.1. 166 - 168 ’C 50 4-CF ₃ -C ₆ H ₄ -CH ₂ 51 2-CH ₃ -3-CF ₃ -C ₆ H ₃ -CH ₂ 52 2-CH ₃ -4-CF ₃ -C ₆ H ₃ -CH ₂ 53 2-CF ₃ -3-CH ₃ -C ₆ H ₃ -CH ₂ 54 2-CF ₃ -4-CH ₃ -C ₆ H ₃ -CH ₂ 55 2-CF ₃ -5-CH ₃ -C ₆ H ₃ -CH ₂ 56 2-CH ₃ -5-CF ₃ -C ₆ H ₃ -CH ₂ 57 2-Br-C ₆ H ₄ CH ₂ 58 3-Br-C ₆ H ₄ CH ₂ 1.1. 103 - 105 'C

4-Br-C ₆ H ₄ CH ₂

2-ÍBopropyl _{CGH-4-CH 2}

3 ~ _{isopropyl-4-CH 2} CGH

4- (5-isopropyl-C ₆ H ₄ -CH ₂₎

2-isopropyl-3-Cl-C ₆ H ₃ CH ₂

_{2-isopropyl-4-Cl-3-CH 2} CGH

2-ŕgopropyl-5-Cl-C ₆ H ₃ CH ₂

2-CH ₃ -3-Isopropyl-5-C 8 H ₃ -CH ₂ i

2-CH ₃ -4-isopropyl-5-C ₆ H ₃ -CH ₂

2-CH ₃ -5-isopropyl-5-C 8 H ₃ 'CH ₂

2-tert-C ₄ H ₉ -C ₆ H ₄ -CH ₂

3-tert-C ₄ H ₉ -C ₆ H ₄ -CH ₂

4-t-C ₄ H _g C ₆ H ₄ CH ₂ NMR: 1.91 (s, 9H), 2.9 (d, 3H);

3.90 (s, 3H), 5.15 (s, 2H),

6.7 (s, 1H) and 7.18-8.0 (m, 9H)

2-CH ₃ -3-tert-C ₄ H ₉ -C ₆ H ₃ -CH ₂ .

2-CH ₃ -4-tert-C ₄ H ₉ -C ₆ H ₃ -CH ₂

Table 1 - continued

Physical parameters [tt ('C), IR (cm ^-1 ), NMR (ppm)]

2louč. number R ²

2-CH ₃ -5-tert-C ₄ H ₉ -C ₆ H ₃ -CH ₂

3-CH ₃ -4-tert-C ₄ H ₉ -C ₆ H ₃ -CH ₂

3-CH ₃ -5-tert-C ₄ H ₉ -C ₆ H ₃ -CH ₂ '

2-Cl-3-tert-C ₄ H ₉ -C ₆ H ₃ -CH ₂

2-Cl-4-tert-C ₄ H ₉ -C ₆ H ₃ -CH ₂

2-Cl-5-tert-C ₄ H ₉ -C ₆ H ₃ -CH ₂

3-Cl-4-tert. -C ₄ H ₉ -C ₆ H ₃ -CH ₂

3-Cl-5-tert. -C ₄ H ₉ -C ₆ H ₃ -CH ₂

2-OCH ₃ -C ₆ H ₄ -CH ₂

3-OCH ₃ -C ₆ H ₄ -CH ₂ NMR: 2.8 (d, 3H), 3.80 (s, 3H),

3.9 (s, 3H); 5.75 ((s, 2H));

6.7 (s, 1H); 6.8-8.0 (m, 9H)

4-OCH ₃ -C ₆ H ₄ -CH ₂

2-CH ₃ -3-OCH ₃ -C ₆ H ₃ -CH ₂

2-CH ₃ -5-OCH ₃ -C ₆ H ₃ -CH ₂

3-CH ₃ -4-OCH ₃ -C ₆ H ₃ -CH ₂

3-CH ₃ -5-OCH ₃ -C ₆ H ₃ -CH ₂

2-C 1-3 -OCH ₃ -C ₆ H ₃ -CH ₂

2-Cl-4-OCH ₃ -C ₆ H ₃ -CH ₂

2-Cl-5-OCH ₃ -C ₆ H ₃ -CH ₂

2-OCH ₃ -3-Cl-C ₆ H ₃ -CH ₂

2-OCH ₃ -4-Cl-C ₆ H ₃ -CH ₂

2-OCH ₃ -5-Cl-C ₆ H ₃ -CH ₂

2-CH ₃ -4-cyclohexyl-C ₆ H ₃ -CH ₂

2-CH ₃ -4-C ₆ H ₅ -C ₆ H ₃ -CH ₂

2-CH ₃ -3-Br-C ₆ H ₃ -CH ₂

2-CH ₃ -4-Br-C ₆ H ₃ -CH ₂

2-CH ₃ -5-Br-C ₆ H ₃ -CH ₂

100 2-CH-J-3- (methoxyiminomethyl) -C ₈ H ₃ -CH ₂

101 2-methoxyiminomethyl-C 8 H ₄ -CH ₄

Table 1 - continued

Physical Parameters ('C'), IR (cm ^-1 ), NMR (ppm)]

Zlouč

number R ² [ 102 _{3-methoxyimino-C6} 103 2-CH ₃ -4- (methoxyimino) 104 2-phenyl-C ₆ H ₄ CH ₂ 105 3-phenyl-C ₆ H ₄ CH ₂ 106 4-phenyl-C ₆ H ₄ CH ₂ 107 2-phenoxy-C ₆ H ₄ CH ₂ 108 _{3-phenoxy-4-CH 2} CGH 109 4-phenoxy-C ₆ H ₄ CH ₂ 110 2-benzyloxy-C ₆ H ₄ CH ₂ 111 3-benzyloxy-C ₆ H ₄ CH ₂ 112 4-benzyloxy-C ₆ H ₄ CH ₂ 113 _{l-naphthyl-CH2} 114 _{2-naphthyl-CH2} 115 _{9-anthryl-CH2} 116 2-CH ₃ -3-C ₆ H ₅ OC ₆ H ₃ -CH ₂ 117 2-CH ₃ -4-C ₆ H ₅ O-C ₆ H ₃ -CH ₂ 118 2-CH ₃ -5-C ₆ H ₅ O-C ₆ H ₃ -CH ₂ 119 3-CH ₃ -4-C ₆ H ₅ OC ₆ H ₃ -CH ₂ 120 4-CH ₃ -5-C ₆ H ₅ OC ₆ H ₃ -CH ₂ 121 2-Cl-3-C ₆ H ₅ OC ₆ H ₃ -CH ₂ 122 2-Cl-4-C ₆ H ₅ OC ₆ H ₃ -CH ₂ 123 2-Cl-5-C ₆ H ₅ OC ₆ H ₃ -CH ₂ 124 3-Cl-4-C ₆ H ₅ OC ₆ H ₃ -CH ₂ 125 3-Cl-5-C ₆ H ₅ OC ₆ H ₃ -CH ₂ 126 2-CH ₃ -4-CO ₂ CH ₃ -C ₆ H ₃ -CH ₂ 127 2-CH ₃ -5-CO ₂ CH ₃ -C ₆ H ₃ -CH ₂ 128 c ₆ h ₅ -ch (ch ₃ ) 129 2-FC ₆ H ₄ -CH (CH ₃ ) 130 3-FC ₆ H ₄ -CH (CH ₃ )

1.1

Í '

ID: 1669, 1526.1035,

979, 819, 754

1.1

105 ° C

Table 1 - continued

2louč.

number R ²

Physical parameters [tt (° C), Ic (cm ^-1 ), NMR (ppm)]

131 4-FC ₆ H ₄ -CH (CH ₃ ) 132 2-Cl-C ₆ H ₄ -CH (CH ₃₎ 1 133 3-Cl-C ₆ H ₄ -CH (CH ₃₎ 134 4-Cl-C ₆ H ₄ -CH (CH ₃₎ NMR: 1.58 (d, 3H) , 2, 9 (d, 3 H), 3.8 (s, 3H) 5.22 (Q, 1H), and 6.69 (S, 1H) and 7, 18 - 8.0 (m, ! 9H) 135 2,3-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) 136 2,4-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) 137 2,5-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) 138 2,6-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) 139 3,4-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) 140 2-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) 141 3-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) 142 4-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) 143 2,3- (CH ₃ ) ₂ -C ₆ H ₃ -CH (CH ₃ ) 144 2,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH (CH ₃ ) 145 2,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH (CH ₃ ) mp 114 • c 146 3,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH (CH ₃ ) 147 3,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH (CH ₃ ) 148 4,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH (CH ₃ ) 150 2,3,4- (CH ₃ ) ₃ -C ₆ H ₂ -CH (CH ₃ ) 151 2,4,5- (CH ₃ ) ₃ -C ₆ H ₂ -CH (CH ₃ ) 152 2,4,6- (CH ₃ ) ₃ -C ₆ H ₂ -CH (CH ₃ ) 153 2,3,6- (CH ₃ ) ₃ -C ₆ H ₂ -CH (CH ₃ ) 154 2-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) 155 3-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) NMR: 1.6 (d, 3H); 2.9 (d, 3H) 3.85 (s, 3H) 5.3 (Q, 1H), 6.8

(s, 1H), and 7.1-8.0 (m, 9H)

156 4-CF ₃ -C ₆ H ₄ -CH (CH ₃ )

Table 1 - continued

Zlouč. . Physical parameters

number R ² [tt (° C), IR (cm ^-1 ), NMR (ppm)] 157 2-CH ₃ -3-CF ₃ -C ₆ H ₃ -CH (CH ₃ ) 158 2-CH ₃ -4-CF ₃ -C ₆ H ₃ -CH (CH ₃ ) ₍ 159 2-CH ₃ -3-CH ₃ -C ₆ H ₃ -CH (CH ₃ ) 160 2-CH ₃ -4-CH ₃ -C ₆ H ₃ -CH (CH ₃ ) 161 2-CH ₃ -5-CH ₃ -C ₆ H ₃ -CH (CH ₃ ) 162 2-CH ₃ -5-CF ₃ -C ₆ H ₃ -CH (CH ₃ ) 163 2-Br-C ₆ H ₄ -CH (CH ₃ ) 164 3-Br-C ₆ H ₄ -CH (CH ₃ ) 165 4-Br-C ₆ H ₄ -CH (CH ₃ ) 166 2-isopropyl-C ₆ H ₄ -CH (CH ₃₎ 167 3-Isopropyl-C ₆ H ₄ -CH (CH ₃ ) 168 Í2opropyl 4-C ₆ H ₄ -CH (CH ₃₎ 169 2-Í2Opropyl-3-Cl-C ₆ H ₃ CH (CH ₃₎ 170 2-Í2opropyl-4-Cl-C ₆ H ₃ CH (CH ₃₎ 171 2-Í2opropyl-5-C-CGH ₃ CH (CH ₃₎ 172 2-CH ₃ -3-isopropyl-C 8 H ₃ -CH (CH ₃ ) 173 2-CH ₃ -4-isopropyl-C 8 H ₃ -CH (CH ₃ ) 174 2-CH ₃ -5-isopropyl-C ₆ H ₃ -CH (CH ₃ ) 175 2-tert-C ₄ H _g -C ₆ H ₄ -CH (CH ₃ ) 176 3-tert-C ₄ H ₉ -C ₆ H ₄ -CH (CH ₃ ) 177 4-tert-C ₄ H ₉ -C ₆ H ₄ -CH (CH ₃ ) 178 2-CH ₃ -3-tert-C ₄ H _g -C ₆ H ₃ -CH (CH ₃ ) 179 2-CH ₃ -4-tert-C ₄ H _g -C ₆ H ₃ -CH (CH ₃ ) 180 2-CH ₃ -5-tert-C ₄ H _g -C ₆ H ₃ -CH (CH ₃ ) 181 3-CH ₃ -4-tert-C ₄ H _g -C ₆ H ₃ -CH (CH ₃ ) 182 3-CH ₃ -5-tert-C ₄ H _g -C ₆ H ₃ -CH (CH ₃ ) 183 2-Cl-3-t-C ₄ H _g -CgH ₃ CH (CH ₃₎ 184 2-Cl-4-tert-C ₄ H _g -C ₆ H ₃ -CH (CH ₃ ) - 185 3-Cl-4-tert-C ₄ H _g -C ₆ H ₃ -CH (CH ₃ ) 187 3-Cl-5-tert-C ₄ H _g -C ₆ H ₃ -CH (CH ₃ )

Table 1 - continued

21ouč.

number

Physical parameters [tt (° C), IR (cm ¹ ), NMR (ppm)]

188 2-OCH ₃ -C ₆ H ₄ -CH ₂ -CH (CH ₃ )

189 j 3-OCH ₃ -C ₆ H ₄ -CH ₂ -CH (CH ₃ )

190 '4-OCH ₃ -C ₆ H ₄ -CH ₂ -CH (CH ₃ )

191 2-CH ₃ -3-OCH ₃ -C ₈ H ₃ -CH (CH ₃ ).

192 2-CH ₃ -4-OCH ₃ -C ₆ H ₃ -CH (CH ₃ )

193 2-CH ₃ -5-OCH ₃ -C ₈ H ₃ -CH (CH ₃ )

194 3-CH ₃ -4-OCH ₃ -C ₈ H ₃ -CH (CH ₃ )

195 3-CH ₃ -5-OCH ₃ -C ₈ H ₃ -CH (CH ₃ )

196 2-C1-3-OCH ₃ -C ₈ H ₃ -CH (CH ₃ )

197 2-Cl-4-OCH ₃ -C ₈ H ₃ -CH (CH ₃ )

198 2-Article-5-OCH ₃ -C ₈ H ₃ -CH (CH ₃ )

199 2-OCH ₃ -3-Cl-C 8 H ₃ -CH (CH ₃ )

200 2-OCH ₃ -4-Cl-C 8 H ₃ -CH (CH ₃ )

201 2-OCH ₃ -5-Cl-C 8 H ₃ -CH (CH ₃ )

202 2-CH ₃ -4-cyclohexyl-C 8 H ₃ -CH (CH ₃ )

203 2-CH ₃ -4-C ₈ H ₅ -C ₈ H ₃ -CH (CH ₃ )

204 2-CH ₃ -3-Br-C ₆ H ₃ -CH (CH ₃ )

205 2-CH ₃ -4-Br-C 8 H ₃ -CH (CH ₃ )

206 2-CH ₃ -5-Br-C 8 H ₃ -CH (CH ₃ )

207 2-CH ₃ -3- (methoxyiminomethyl) -C ₈ H ₃ -CH (CH ₃ )

208 2-methoxyimino-CGH ₄ -CH (CH ₃₎

209 3-methoxyimino-CGH CH ₄ '(CH ₃₎

210 2-CH ₃ -4- (methoxyiminomethyl) -C ₈ H ₃ -CH (CH ₃ )

211 2-phenyl-CGH ₄ -CH (CH ₃₎

212 3-phenyl-CGH ₄ -CH (CH ₃₎

213 4-phenyl-CGH ₄ -CH (CH ₃₎

214 2-phenoxy-CGH ₄ -CH (CH ₃₎

215 3-phenoxy-CGH ₄ -CH (CH ₃₎

216, 4-phenoxy-CGH ₄ -CH (CH ₃₎

217 2-Benzyloxy-CGH ₄ -CH (CH ₃₎

Table 1 - continued

Physical parameters [tt (° C), IR (cm ¹ ), NMR (ppm)]

Zlouč. number R ²

218 3-benzyloxy-CGH ₄ -CH (CH ₃₎

219 4-benzyloxy-CGH ₄ -CH (CH ₃₎

220 l-naphthyl-CH (CH ₃₎

221 2-naphthyl-CH (CH ₃₎

222 9-anthryl-CH (CH ₃₎

223 2-CH ₃ -3-C ₆ H ₅ OC ₆ H ₃ -CH (CH ₃ )

224 2-CH ₃ -4-C ₆ H ₅ OC ₆ H ₃ -CH (CH ₃ )

225 2-CH ₃ -5-C ₆ H ₅ -C ₆ H ₃ -CH (CH ₃ )

226 3-CH ₃ -4-C ₆ H ₅ OC ₆ H ₃ -CH (CH ₃ )

227 4-CH ₃ -5-C ₆ H ₅ OC ₆ H ₃ -CH (CH ₃ )

228 2-Cl-3-C ₆ H ₅ OC ₆ H ₃ -CH (CH ₃ )

229 2-Cl-4-C ₆ H ₅ OC ₆ H ₃ -CH (CH ₃ )

230 2-Cl-5-C ₆ H ₅ OC ₆ H ₃ -CH (CH ₃ )

231 3-Cl-4-C ₆ H ₅ OC ₆ H ₃ -CH (CH ₃ )

232 3-Cl-5-C ₆ H ₅ OC ₆ H ₃ -CH (CH ₃ )

233 2-CH ₃ -4-CO ₂ CH ₃ -C ₆ H ₃ -CH (CH ₃ )

234 2-CH ₃ -5-CO ₂ CH ₃ -C ₆ H ₃ -CH (CH ₃ )

235 C ₆ H ₅ - (CH ₂ ) ₂

236 2-FC ₆ H ₄ - (CH ₂ ) ₂

237 3-FC ₆ H ₄ - (CH ₂ ) ₂

238 4-FC ₆ H ₄ - (CH ₂ ) ₂

239 2-Cl-C ₆ H ₄ - (CH _{2) 2}

240 3-Cl-C ₆ H ₄ - (CH _{2) 2}

241 4-Cl-C ₆ H ₄ - (CH _{2) 2}

242 2,3-Cl ₂ -C ₆ H ₃ - (CH ₂ ) ₂

243.2, 4-Cl ₂ -C ₆ H ₃ - (CH ₂ ) ₂

244 2,5-Cl ₂ -C ₆ H ₃ - (CH ₂ ) ₂

245 2,6-Cl ₂ -C ₆ H ₃ - (CH ₂ ) ₂

246 3,4-Cl ₂ -C ₆ H ₃ - (CH ₂ ) ₂

247 2-CH ₃ -C ₆ H ₄ - (CH ₂ ) ₂

Table 1 - continued.

Physical parameters [tt (° C), IR (cm ¹ ), NMR (ppm)]

Zlouč.

number

248 3-CH ₃ -C ₆ H ₄ - (CH ₂ ) ₂

249 i 4-CH ₃ -C ₆ H ₄ - (CH ₂ ) ₂

250 '2,3- (CH ₃ ) ₂ -C ₆ H ₃ - (CH ₂ ) ₂

251 2,4- (CH ₃ ) ₂ -C ₆ H ₃ - (CH ₂ ) ₂

252 2,5- (CH ₃ ) ₂ -C ₆ H ₃ - (CH ₂ ) ₂

253 3,4- (CH ₃ ) ₂ -C ₆ H ₃ - (CH ₂ ) ₂

254 3,5- (CH ₃ ) ₂ -C ₆ H ₃ - (CH ₂ ) ₂

255 4,5- (CH ₃ ) ₂ -C ₆ H ₃ - (CH ₂ ) ₂

256 2,3,4- (CH ₃ ) ₃ -C ₆ H ₂ - (CH ₂ ) ₂

257 2,4,5- (CH ₃ ) ₃ -C ₆ H ₂ - (CH ₂ ) ₂

258 2-, 4,6- (CH ₃ ) ₃ -C ₆ H ₂ - (CH ₂ ) ₂

259 2,3,6- (CH ₃ ) ₃ -C ₆ H ₂ - (CH ₂ ) ₂

260 2-CF ₃ -C ₆ H ₄ - (CH ₂ ) ₂

261 3-CF ₃ -C ₆ H ₄ - (CH ₂ ) ₂

262 4-CF ₃ -C ₆ H ₄ - (CH ₂ ) ₂

263 2-CH ₃ -3-CF ₃ -C ₆ H ₃ - (CH ₂ ) ₂

264 2-CH ₃ -4-CF ₃ -C ₆ H ₃ - (CH ₂ ) ₂

265 2-CF ₃ -3-CH ₃ -C ₆ H ₃ - (CH ₂ ) ₂

266 2-CF ₃ -4-CH ₃ -C ₆ H ₃ - (CH ₂ ) ₂

267 2-CF ₃ -5-CH ₃ -C ₆ H ₃ - (CH ₂ ) ₂

268 2-CH ₃ -3-CF ₃ -C ₆ H ₃ - (CH ₂ ) ₂ >

.269 2-Br-C ₆ H ₄ - (CH _{2) 2}

270 3-Br-C ₆ H ₄ - (CH ₂ ) ₂

271 4-Br-C ₆ H ₄ - (CH ₂ ) ₂

272 2-Isopropyl-C ₆ H ₄ - (CH ₂ ) ₂

273 3-Í2opropyl _4-CGH - _{(CH2) 2}

274 4- (2-propyl-C ₆ H ₄ - (CH ₂ ) ₂₎

275 _{2-Isopropyl-3-C-3} CGH - (CH _{2) 2}

276; 2-Í2opropyl-4-Cl-C ₆ H ₃ - (CH _{2) 2}

277 2-Isopropyl-5-Cl-C ₆ H ₃ - (CH _{2) 2}

Table 1 - continued

Zlouč. Physical parameters number R ² [tt ('C), IR (cm ^-1 ), NMR (ppm)]

278 2-CH ₃ -3-Isopropyl-C 8 H ₃ - (CH ₂ ) ₂

279 2-CH ₃ -4-isopropyl-C 8 H ₃ - (CH ₂ ) ₂

280 2-CH ₃ -5-Isopropyl-C ₆ H ₃ - (CH ₂ ) ₂

281 2-tert-C ₄ H ₉ -C ₈ H ₄ - (CH ₂ ) ₂

282 3-tert-C ₄ H ₉ -C ₆ H ₄ - (CH ₂ ) ₂

283 4-t. ~ C ₄ H _g -CgH ₄ - (CH _{2) 2}

284 2-CH ₃ -3-t-C ₄ H _g -CgH ₃ - (CH _{2) 2}

285 _2-CH3 -4-t-C ₄ H _g -CgH ₃ - (CH _{2) 2}

286 _2-CH3 -5-tert-C ₄ H · _g -CgH ₃ "(CH _{2) 2}

287 _3-CH3 -4-t-C ₄ H _g -CgH ₃ - (CH _{2) 2}

288 _3-CH3 -5-t-C ₄ H _g -CgH ₃ - (CH _{2) 2}

289 2-Cl-3-t-C ₄ H _g -CgH ₃ ~ _{(CH2) 2}

290 2-Cl-4-t-C ₄ H _g C ₆ H ₃ - (CH _{2) 2}

291 3-Cl-5-tert-C ₄ H _g -CgH ₃ - (CH _{2) 2}

292 3-Cl-4-t-C ₄ H _g -CgH ₃ - (CH _{2) 2}

293 3-Cl-5-tert-C ₄ H _g -CgH ₃ - (CH _{2) 2}

294 2-OCH ₃ -C ₈ H ₄ -CH ₂ - (CH ₂ ) ₂

295 3-OCH ₃ -C ₈ H ₄ -CH ₂ - (CH ₂ ) ₂

296 4-OCH ₃ -C ₈ H ₄ -CH ₂ - (CH ₂ ) ₂

297 2-CH ₃ -3-OCH ₃ -C ₈ H ₃ - (CH ₂ ) ₂

298 2-CH ₃ -4-OCH ₃ -C ₈ H ₃ - (CH ₂ ) ₂

299 2-CR ₃ -5-OCH ₃ -C ₈ H ₃ - (CH ₂ ) ₂

300 3-CH ₃ -4-OCH ₃ -C ₈ H ₃ - (CH ₂ ) ₂

301 3-CH ₃ -5-OCH ₃ -C ₈ H ₃ - (CH ₂ ) ₂

302 2-Cl-3-OCH ₃ -C ₈ H ₃ - (CH ₃ ) ₂

303 2-Cl-4-OCH ₃ -C ₈ H ₃ - (CH ₃ ) ₂

304 2-Cl-5-OCH ₃ -C ₈ H ₃ - (CH ₃ ) ₂

305 2-OCH ₃ -3-Cl-C ₆ H ₃ - (CH ₃ ) ₂

306 2-OCH ₃ -4-Cl-C 8 H ₃ - (CH ₃ ) ₂

307 2-OCH ₃ -5-Cl-C ₆ H ₃ - (CH ₃ ) ₂

Table 1 - continued

Physical parameters [tt ('C), IR (cm ^-1 ), NMR (ppm)]

Zlouč. R ^{* 2}

308

309 ₍

310

311

312

313

314

315

316

317

318

319

320

321

322

323

324

325

326

327

328

329

330

331

332

333

334

335

336

337

308

309 ₍

310

311

312

313

314

315

316

317

318

319

320

321

322

323

324

325

326

327

328

329

330

331

332

333

334

335

336

337

2-CH ₃ -4-cyclohexyl-C 8 H ₃ - (CH ₂ ) ₂

2-CH ₃ -4-C ₆ H ₅ -C ₆ H ₃ - (CH ₂ ) ₂

2-CH ₃ -3-Br-C ₆ H ₃ - (CH ₂ ) ₂

2-CH ₃ -4-Br-C ₆ H ₃ - (CH ₂ ) ₂

2-CH ₃ -5-Br-C ₆ H ₃ - (CH ₂ ) ₂

2-CH ₃ -3- (methoxyiminomethyl) -C ₈ H ₃ - (CH ₂ ) ₂

2-methoxyimino-CGH ^ - _{(CH2) 2}

_{3-methoxyimino-4} CGH - _{(CH2) 2}

2-CH ₃ -4- (methoxyiminomethyl) -C ₈ H ₃ - (CH ₂ ) ₂ 2-phenyl-C ₆ H ₄ - (CH ₂ ) ₂ 1-3-phenyl-C ₆ H ₄ - (CH ₂ ) ₂

4-phenyl-C ₆ H ₄ - (CH ₂ ) ₂

_2-phenoxy-4 CGH - _{(CH2) 2}

_3-phenoxy-4 CGH - _{(CH2) 2}

_4-phenoxy-4 CGH - _{(CH2) 2}

_{2-benzyloxy-4} CGH - _{(CH2) 2}

_{3-benzyloxy-4} CGH - _{(CH2) 2}

4-benzyloxy-C ₆ H ₄ - (CH _{2) 2}

1-naphthyl _{(CH2) 2}

2-naphthyl _{(CH2) 2}

9-anthryl- _{(CH2) 2}

2 ^- CH ₃ -3-C ₆ H ₅ OC ₆ H ₃ - (CH ₂ ) 2 -

2-CH ₃ -4-C ₆ H ₅ OC ₆ H ₃ - (CH ₂ ) ₂

2- CH ₃ -5-C ₆ H ₅ OC ₆ H ₃ - (CH ₂ ) ₂

3- CH ₃ -4-C ₆ H ₅ OC ₆ H ₃ - (CH ₂ ) ₂

4- CH ₃ -5-C ₆ H ₅ O-C ₃ H ₃ - (CH ₂ ) ₂

2-Cl-3-C ₈ H ₅ OC ₆ H ₃ - (CH ₂ ) ₂

2-Cl-4-C ₆ H _{5 0-3} CGH - (CH _{2) 2}

2-Cl-5-CGH ₅ O ₃ CGH - (CH _{2) 2}

3-Cl-4-CGH ₅ OC ₆ H ₃ - (CH _{2) 2}

Table 1 - continued

Physical parameters [tt (° C)], Rt (cm ^-1 ), NMR (ppm).

number

338 3-Cl-5-C ₆ H ₅ O-C ₆ H ₃ - (CH ₂ ) ₂

339 2-CH ₃ -4-CO ₂ CH ₃ -C ₆ H ₃ - (CH ₂ ) ₂

340 2-CH ₃ -5-CO ₂ CH ₃ -C ₆ H ₃ - (CH ₂ ) ₂

341 C ₆ H ₅ -CH = CH-CH ₂

342 2-FC ₆ H ₄ -CH = CH-CH ₂

343 3-FC ₆ H ₄ -CH = CH-CH ₂

344 4-FC ₆ H ₄ -CH = CH-CH ₂

345 2-Cl-C ₆ H ₄ -CH = CH-CH ₂

346 3-Cl-C ₆ H ₄ -CH = CH-CH ₂

347 4-Cl-C ₆ H ₄ -CH = CH-CH ₂

PART; 348 2,3-Cl ₂ -C ₆ H ₃ 'CH = CH-CH ₂

349 2,4-Cl ₂ -C ₆ H ₃ -CH = CH-CH ₂

350 2,5-Cl ₂ -C ₆ H ₃ -CH = CH-CH ₂

351 2,6-Cl ₂ -C ₆ H ₃ -CH = CH-CH ₂

352 3,4-Cl ₂ -C ₆ H ₃ -CH = CH-CH ₂

353 2-CH ₃ -C ₆ H ₄ -CH = CH-CH ₂

354 3-CH ₃ -C ₆ H ₄ -CH = CH-CH ₂

355 4-CH ₃ -C ₆ H ₄ -CH = CH-CH ₂

356 2,3- (CH ₃ ) ₂ -C ₆ H ₃ -CH = CH-CH ₂

357 2,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH = CH-CH ₂

358. 2,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH = CH-CH ₂

359 i 3,4 - (CH ₃ ) ₂ -C ₆ H ₃ -CH = CH-CH ₂

360 3,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH = CH-CH ₂

361 4,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH = CH-CH ₂

362 2,3,4- (CH ₃ ) ₃ -C ₆ H ₂ -CH = CH-CH ₂

363 2,4,5- (CH ₃ ) ₃ -C ₈ H ₂ -CH = CH-CH ₂

364 2,4,6- (CH ₃ ) ₃ -C ₆ H ₂ -CH = CH-CH ₂

365 2,3,6- (CH ₃ ) ₃ -C ₆ H ₂ -CH = CH-CH ₂

366 2-CF ₃ -C ₆ H ₄ -CH = CH-CH ₂

367 3-CF ₃ -C ₆ H ₄ -CH = CH-CH ₂

Table 1 - continued

Zlouč. Physical parameters number R ² [tt (° C), IR (cm ^{- 1} ·), NMR (ppm)]

368 4-cf ₃ -c ₆ h ₄ -ch = ch-ch ₂ 369, 2-CH ₃ -3-CF ₃ -C ₆ H ₃ -CH = CH-CH ₂ 370 ' 2-CH ₃ -4-CF ₃ -C ₆ H ₃ -CH = CH-CH ₂ 371 2-CF ₃ -3-CF ₃ -C ₆ H ₃ -CH = CH-CH ₂ 372 2-CF ₃ -4-CF ₃ -C ₆ H ₃ -CH = CH-CH ₂ 373 2-CF ₃ -5-CF ₃ -C ₆ H ₃ -CH = CH-CH ₂ 374 2-CH ₃ -5-CF ₃ -C ₆ H ₃ -CH = CH-CH ₂ 375 c ₆ h ₅ - (ch ₂ ) ₃ 376 C ₆ ^h 5- ( ^ch 2) 4 377 c ₆ h ₅ -ch ₂ ch = ch-ch ₂ 378 4-F-CH-CH = CH- (CH) ₂ 379 ch ₃ o-what-ch ₂ 380 ch ₃ ch ₂ o-what-what ₂ 381 ch ₃ -co-ch ₂ -ch ₂ 382 tert-C ₄ H ₉ O-CO-CH ₂ 383 tert-C ₄ H ₉ O-CO- (CH ₂ ) ₂ 384 t-C ₄ H ₉ O-CO-CH (CH ₃ ) NMR: 1.42 (d, 9H), 1.5 (s, 9H) 2.96 (d, 3H), 3.97 (s, 3H), 4.62 (q, 9H); 6.87 (s, 1H); 7.18 - 8.0 (m, 9H)

385 nC ₄ H ₉ O-CO-CH ₂

386 ° C ₄ H _g O-CO-CH ₂

387 nC ₃ H ₇ O-CO-CH ₂

388 sec-C ₄ H ₉ O-COCH ₂

389 C ₆ H ₅ -CO-CH ₂

390 2-CH ₃ -C ₆ H ₄ O-CO-CH ₂

391 3-CH ₃ -C ₆ H ₄ O-CO-CH ₂

392 4-CH ₃ -C ₆ H ₄ O-CO-CH ₂

393. 2-Cl-C ₆ H ₄ O-CO-CH ₂

394 3-Cl-C 8 H ₄ O-CO-CH ₂

Table 1 - continued

Physical parameters [tt ('C), IR (cm ^-1 ), NMR (ppm)]

21ouč. number R ²

395 4-Cl-C ₆ H ₄ O-CO-CH ₂

396 C ₆ H ₅ -C (CH ₃ ) = CH-CH ₂

ID: 1662, 1527, 1445,

1035, 987,775

397

ch ₂

398

Cl ch ₂

Cl

399

ch ₂

400

ch ₃ ch ₂ ch ₃

401

ch ₂ cf ₃ ch ₂

402

Table 1 - continued

Physical parameters [tt (° C), IR (cm ^-1 ), NMR (ppm) J

21ouč. number R ²

br

404

ch ₂

405

F

CH ₂

406

407

408

409

410

Cl

411

ch ₃ ch ₂

412

Table 1 - continued

Physical parameters [tt (° C), IR (cm ^-1 ), NMR (ppm) J

21ouč.

number ch ₃

413

br

CH ₂

414

415 ch ₃

br

CH ₂

416

CH ₃

ch ₃ ch ₂

419

Cl

Cl ch ₂

420

421 ch ₂

Table 1 - continued.

Zlouč.

number R ²

Physical parameters [tt (° C), IR (cm ¹ ), NMR (ppm)]

422

423 and ₃

Cl ch ₂

Cl

F ch ₂

⁴²⁷ TJL _C h ₂

-ABOUT

Table 1 - continued.

21ouč.

number R ²

Physical parameters.

[tt (C), IR (cm ^-1 ), NMR (ppm)]

433

Π íl

434 N - _n --CH ₂

CH ₂

Table 1 - continued

Physical parameters.

[tt ('C), IR (cm ^-1 ), NMR (ppm)]

21ouč.

number

mp 95-97 ’C

Table 1 - continued.

Zlouč. Physical parameters

459

461

462

463 ch ₃

ch ₂ n = c-ch ₂ t-C ₄ H ₉ O-CH ₂ -CH = CH-CH ₂

464 (CH ₃ ) ₂ -C =CH-CH ₂ -CH ₂ -C (CH ₃ ) = CH-CH ₂

Table 1 - continued.

Zlouč. number R ²

Physical parameters [tt (C), IR (cm ^-1 ), NMR (ppm)]

465 (ch ₃ ) ₂ ch-c = ch-ch ₂ -ch ₂ -c (ch ₃ ) = CH -ch ₂ 466 ^C 6 ^H 5 ^{-O- CH} 3 ^CH 3> ^-C 12 467 4-Cl-C ₆ H ₄ -O-CH _{(CH3) -CH2-NMR:} 1.3 (d, 3H); 2.9 (d, 3H); 3.9 (s, 3H); 4.1 - 4.35 (M, 2H), 4.65 (M, 1H), 6.8 - 7.9 (m, 10H)

Table 2

CH ₃ θ ^ Ν · ⁰ '^ ch ₃ ^k h

Zlouč.

R ² v

^CH ₃ ^CH 3 ^CH 2 ^CH 3 ^CH 2 ^CH 2 = ^CH-CH 2 ^CH 2 = C (C 1) -CH 2 CH 3 -CH = CH-CH (CH 3) CH 2 = C (CH 3) -CH 2 ^C 2 ^H 5 ^{-O- CH} 2 " ^CH 2 c-ch ₂ -ch ₂ cyclo-C ₃ H ₅ -CH ₂ ch ₃ -ch = ch-ch ₂ ch ₂ = ch-ch ₂ -ch ₂ ch ₃ -c = c -ch ₂ . CH ₃ CH ₂ -C? C-CH ₂ CH ₃ - (CH _{2) 3} CH ₃ - (CH _{2) 4} (CH _{3) 3} C ₆ cycloalkyl C H _{i, S} 2-CH-J-cyclo-C ₆ CgHjQ h ₅ -ch ₂

2-FC ₆ H ₄ -CH ₂

3-FC ₆ H ₄ -CH ₂

Table 2 - continuation Zlouč. number R ² 26 4-FC ₆ H ₄ -CH ₂ 27 2-Cl-C ₆ H ₄ CH ₂ 28 3-Cl-C ₆ H ₄ CH ₂ 29 4-Cl-C ₆ H ₄ CH ₂ 30 2,3-Cl ₂ -C ₆ H ₃ -CH ₂ 31 2,4-Cl ₂ -C ₆ H ₃ -CH ₂ 32 3,5-Cl ₂ -C ₆ H ₃ -CH ₂ 33 2,6-Cl ₂ -C ₆ H ₃ -CH ₂ 34 3,4-Cl ₂ -C ₆ H ₃ -CH ₂ 35 2-CH ₃ -C ₆ H ₄ -CH ₂ 37 4-CH ₃ -C ₆ H ₄ -CH ₂ 38 2,3- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ 39 2,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ 40 2,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ 41 3,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ 42 3,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ 43 4,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ 44 2,3,4- (CH ₃ ) ₃ -C ₆ H ₂ -CH 45 2,4,5- (CH ₃ ) ₃ -C ₆ H ₂ -CH 46 2,4,6- (CH ₃ ) ₃ -C ₆ H ₂ -CH 47 2,3,6- (CH ₃ ) ₃ -C ₆ H ₂ -CH 48 2-CF ₃ -C ₆ H ₄ -CH ₂ 49 3-CF ₃ -C ₆ H ₄ -CH ₂ 50 4-CF ₃ -C ₆ H ₄ -CH ₂ 51 2-CH ₃ -3-CF ₃ -C ₆ H ₃ -CH ₂ 52 2-CH ₃ -4-CF ₃ -C ₆ H ₃ -CH ₂ 53 2-CF ₃ -3-CH ₃ -C ₆ H ₃ -CH ₃ 54 2-CF ₃ -4-CH ₃ -C ₆ H ₃ -CH ₂ 55 2-CF ₃ -5-CH ₃ -C ₆ H ₃ -CH ₂ 56 2-CH ₃ -5-CF ₃ -C ₆ H ₃ -CH ₂

Table 2 - continuation 21ouč. number R ² 57 2-Br-C ₆ H ₄ CH ₂ 58 3-Br-C ₆ H ₄ CH ₂ 59 4-Br-C ₆ H ₄ CH ₂ 60 2-isopropyl-C ₆ H ₄ CH ₂ 61 _{3-isopropyl-4-CH 2} CGH 62 Í2opropyl 4-C ₆ H ₄ CH ₂ 63 2-isopropyl-3-Cl-C ₆ H ₃ CH ₂ 64 _{2-isopropyl-4-Cl-3-CH 2} CGH 65 2-isopropyl-5-Cl-C ₆ H ₃ CH ₂ 66 2-CH ₃ -3-isopropyl-5-C 8 H ₃ -CH 67 2-CH ₃ -4-isopropyl-5-C 8 H ₃ -CH 68 2-CH ₃ -5-isopropyl-5-C ₆ H ₃ -CH. 69 2-t-C ₄ H _g C ₆ H ₄ CH ₂ 70 3-tert-C ₄ H ₉ -C ₆ H ₄ -CH ₂ 71 4-t-C ₄ H _g C ₆ H ₄ CH ₂ 72 2-CH ₃ -3-t-C ₄ H _g C ₆ H ₃ CH ₂ 73 2-CH ₃ -4-t-C ₄ H _g C ₆ H ₃ -CH ₂ 74 _2-CH3 -5-t-C ₄ H _g C ₆ H ₃ CH ₂ 75 3-CH ₃ -4-t-C ₄ H _g C ₆ H ₃ CH ₂ 76 _3-CH3 -5-t-C ₄ H _g C ₆ H ₃ CH ₂ 77: 2-Cl-3-tert-C ₄ H _g -C ₆ H ₃ -CH ₂ ' 78 í 2-Cl-4-t-C ₄ H _g C ₆ H ₃ CH ₂ 79 2-Cl-5-tert-C ₄ H _g C ₆ H ₃ CH ₂ 80 3-Cl-4-t-C ₄ H _g C ₆ H ₃ CH ₂ 81 3-Cl-5-tert-C ₄ H _g C ₆ H ₃ CH ₂ 82 2-OCH ₃ -C ₆ H ₄ -CH ₂ 83 3-OCH ₃ -C ₆ H ₄ -CH ₂ 84 4-OCH ₃ -C ₆ H ₄ -CH ₂ 85 2-CH ₃ -3-OCH ₃ -C ₈ H ₃ -CH ₂ 86 2-CH ₃ -5-OCH ₃ -C ₆ H ₃ -CH ₂

Table 2 - continued

Zlouč. number R ² 87 3-CH ₃ -4-OCH ₃ -C ₆ H ₃ -CH ₂ 88 3-CH ₃ -5-OCH ₃ -C ₆ H ₃ -CH ₂ 89 2-Cl-3-OCH ₃ -C ₆ H ₃ -CH ₂ 90 2-Cl-4-OCH ₃ -C ₆ H ₃ -CH ₂ 91 2-Cl-5-OCH ₃ -C ₆ H ₃ -CH ₂ 92 2-OCH ₃ '3-Cl-C ₆ H ₃ -CH ₂ 93 2-OCH ₃ -4-Cl-C ₆ H ₃ -CH ₂ 94 2-OCH ₃ -5-Cl-C ₆ H ₃ -CH ₂ 95 2-CH ₃ -4-cyclohexyl-C ₆ H ₃ -CH ₂ 96 2-CH ₃ -4-C ₆ H ₅ -C ₆ H ₃ -CH ₂ 97 2-CH ₃ -3-Br-C ₆ H ₃ -CH ₂ 98 2-CH ₃ -4-Br-C ₆ H ₃ -CH ₂ 99 2-CH ₃ -5-Br-C ₆ H ₃ -CH ₂ 100 2-CH ₃ -3- (methoxyiminomethyl) -C ₈ H ₃ -CH ₂ 101 2-methoxyimino-methyl-C ₆ H ₄ CH ₄ 102 3-methoxyimino-methyl-C ₆ H ₄ CH ₄ 103 2-CH ₃ -4- (methoxyiminomethyl) -C ₆ H ₃ -CH ₂ 104 2-phenyl-C ₆ H ₄ CH ₂ 105 3-phenyl-C ₆ H ₄ CH ₂ 106 4-phenyl-C ₆ H ₄ CH ₂ 107 2-phenoxy-C ₆ H ₄ CH ₂ 108 3-phenoxy-C ₆ H ₄ -CH ₂ 109 4-phenoxy-C ₆ H ₄ CH ₂ 110 2-benzyloxy-C ₆ H ₄ CH ₂ 111 _{3-benzyloxy-4-CH 2} CGH 112 _{4-benzyloxy-4 -CH2} CGH 113 _{l-naphthyl-CH2} 114 _{2-naphthyl-CH2} 115 _{9-anthryl-CH2} 116 2-CH ₃ -3-C ₆ H ₅ OC ₆ H ₃ -CH ₂

Table 2 - continued

Zlouč.

number R ² 117 2-CH ₃ -4-C ₆ H ₅ OC ₆ H ₃ -CH ₂ 118 2-CH ₃ -5-C ₆ H ₅ OC ₆ H ₃ -CH ₂ 119 3-CH ₃ -4-C ₆ H ₅ OC ₆ H ₃ -CH ₂ 120 4-CH ₃ -5-C ₆ H ₅ OC ₆ H ₃ -CH ₂ 121 2-Cl-3-C ₆ H ₅ OC ₆ H ₃ -CH ₂ 122 2-Cl-4-C ₆ H ₅ OC ₆ H ₃ -CH ₂ 123 2-Cl-5-C ₆ H ₅ OC ₆ H ₃ -CH ₂ 124 3-Cl-4-C ₆ H ₅ OC ₆ H ₃ -CH ₂ 125 3-Cl-5-C ₆ H ₅ OC ₆ H ₃ -CH ₂ 126 2-CH ₃ -4-CO ₂ CH ₃ -C ₆ H ₃ -CH ₂ 127 2-CH ₃ -5-CO ₂ CH ₃ -C ₆ H ₃ -CH ₂ 128 c ₆ h ₅ -ch (ch ₃ ) 129 2-FC ₆ H ₄ -CH (CH ₃ ) 130 3-FC ₆ H ₄ -CH (CH ₃ ) 131 4-FC ₆ H ₄ -CH (CH ₃ ) 132 2-Cl-C ₆ H ₄ -CH (CH ₃₎ 133 3-Cl-C ₆ H ₄ -CH (CH ₃₎ 134 4-Cl-C ₆ H ₄ -CH (CH ₃ ) 135 2,3-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) 136 2,4-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) 137 2,5-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) 138: 2,6-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) 139 3,4-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) 140 2-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) 141 3-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) 142 4-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) 143 2,3- (CH ₃ ) ₂ -C ₆ H ₃ -CH (CH ₃ ) 144 2,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH (CH ₃ ) 145 2,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH (CH ₃ ) 146 3,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH (CH ₃ )

Table 2 · - continuation 21ouč. number R ² 147 3,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH (CH ₃ ) 148 4,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH (CH ₃ ) 150 2,3,4- (CH ₃ ) ₃ -C ₆ H ₂ -CH (CH ₃ ) 151 2,4,5- (CH ₃ ) ₃ -C ₆ H ₂ -CH (CH ₃ ) 152 2,4,6- (CH ₃ ) ₃ -C ₆ H ₂ -CH (CH ₃ ) 153 2,3,6- (CH ₃ ) ₃ -C ₆ H ₂ -CH (CH ₃ ) 154 2-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) 155 3-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) 156 4-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) 157 2-CH ₃ -3-CF ₃ -C ₆ H ₃ -CH (CH ₃ ) 158 2-CH ₃ -4-CF ₃ -C ₆ H ₃ -CH (CH ₃ ) 159 2-CH ₃ -3-CH ₃ -C ₆ H ₃ -CH (CH ₃ ) 160 2-CH ₃ -4-CH ₃ -C ₆ H ₃ -CH (CH ₃ ) 161 2-CH ₃ -5-CH ₃ -C ₆ H ₃ -CH (CH ₃ ) 162 2-CH ₃ -5-CF ₃ -C ₆ H ₃ -CH (CH ₃ ) 163 2-Br-C ₆ H ₄ -CH (CH ₃ ) 164 3-Br-C ₆ H ₄ -CH (CH ₃ ) 165 4-Br-C ₆ H ₄ -CH (CH ₃ ) 166 Í2opropyl 2 -C ₆ H ₄ -CH (CH ₃₎ 167 3-Isopropyl-C ₆ H ₄ -CH (CH ₃ ) 168 Í2opropyl 4-C ₆ H ₄ -CH (CH ₃₎ 169 i 2-isopropyl-3-Cl-C ₆ H ₃ CH (CH ₃₎ 170 2-isopropyl-4-Cl-CGH ₃ CH (CH ₃₎ 171 2-isopropyl-5-Cl-C ₆ H ₃ CH (CH ₃₎ 172 2-CH ₃ -3-Isopropyl-C ₆ H ₃ -CH (CH ₃ ) 173 2-CH ₃ -4-isopropyl-C ₆ H ₃ -CH (CH ₃ ) 174 2-CH ₃ -5-isopropyl-C ₆ H ₃ -CH (CH ₃ ) 175 2-tert-C ₄ H _g -C ₆ H ₄ -CH (CH ₃ ) 176 3-tert-C ₄ H ₉ -C ₆ H ₄ -CH (CH ₃ ) 177 4-tert-C ₄ H ₈ -C ₆ H ₄ -CH (CH ₃ )

Table 2 - continued

Zlouč.

number R ²

178

179

180

181

182

183

184

185

187

188

189

190

191

192

193

194

195

196

197

198

199

200

201

202

203

204

205

206

207

208

2-CH ₃ -3-tert-C ₄ H _g -C ₆ H ₃ -CH (CH ₃ ) 2-CH ₃ -4-tert-C ₄ H ₉ -C ₆ H ₃ -CH (CH ₃ )

2- CH ₃ -5-tert-C ₄ H _g -C ₆ H ₃ -CH (CH ₃ )

3-CH ₃ -4-tert-C ₄ H ₉ -C ₆ H ₃ -CH (CH ₃ ) 3 -CH ₃ -5-tert-C ₄ H _g -C ₆ H ₃ -CH (CH ₃ ) 2-Cl-3-tert-C ₄ H ₉ -C ₆ H ₃ -CH (CH ₃ )

2-Cl-4-tert-C ₄ H ₉ -C ₆ H ₃ -CH (CH ₃ )

3-Cl-4-t-C ₄ H _g -C ₆ H ₃ -CH (CH ₃ ) 3 -Cl-5-t-C ₄ H _g -C ₆ H ₃ -CH (CH ₃ )

_{2-OCH3-C 6} H ₄ -CH ₂ -CH _(CH3)

_{3-OCH3-C 6} H ₄ -CH ₂ -CH _(CH3)

_{4-OCH3-C 6} H ₄ -CH ₂ -CH _(CH3)

2-CH ₃ -3-OCH ₃ -C ₆ H ₃ -CH (CH ₃ )

2- CH ₃ -4-OCH ₃ -C ₆ H ₃ -CH (CH ₃ )

3- CH ₃ -5-OCH ₃ -C ₆ H ₃ -CH (CH ₃ ) 3-CH ₃ -4-OCH ₃ -C ₆ H ₃ -CH (CH ₃ ) 3-CH ₃ -5-OCH ₃ - C ₆ H ₃ -CH (CH ₃ ) 2-Cl-3-OCH ₃ -C ₆ H ₃ -CH (CH ₃ ) 2-Cl-4-OCH ₃ -C ₆ H ₃ -CH (CH ₃ ) 2- Cl-5-OCH ₃ -C ₆ H ₃ -CH (CH ₃ ) 2 -OCH ₃ -3-Cl-C ₆ H ₃ -CH (CH ₃ ) 2-OCH ₃ -4-Cl-C ₆ H ₃ - CH (CH ₃ ) 2-OCH ₃ -5-Cl ₃ C ₆ H ₃ -CH (CH ₃ ) 2 -CH ₃ -4-cyclohexyl-C ₆ H ₃ -CH (CH ₃ ) 2 -CH ₃ -4- C ₆ H ₅ -C ₆ H ₃ -CH (CH ₃ ) 2 -CH ₃ -3-Br-C ₆ H ₃ -CH (CH ₃ ) 2 -CH ₃ -4-Br-C ₆ H ₃ -CH (CH ₃ ) 2-CH ₃ -5-Br-C ₆ H ₃ -CH (CH ₃ )

2-CH ₃ -3- (methoxyiminomethyl) -C ₆ H ₃ -CH (CH ₃ ) 2-methoxyiminomethyl-C ₆ H ₄ -CH (CH ₃ )

Table 2 - continued.

Zlouč.

number R ² 209 3-Inethoxyimino-methyl-C ₆ H ₄ -CH (CH ₃ ) 210 2-CH ₃ -4- (methoxyiminomethyl) -C ₆ H ₃ -CH (CH ₃ ) 211 2-phenyl-C ₆ H ₄ -CH (CH ₃ ) 212 3-phenyl-C ₆ H ₄ -CH (CH ₃ ) '213 214 4-phenyl-C ₆ H ₄ -CH (CH ₃ ) 2 -phenoxy-C ₆ H ₄ -CH (CH ₃ ) . 215 3-phenoxy-C ₆ H ₄ -CH (CH ₃₎ 216 4-phenoxy-CGH ₄ -CH (CH ₃₎ 217 2-benzyloxy-C ₆ H ₄ -CH (CH ₃₎ 218 3-benzyloxy-C ₆ H ₄ -CH (CH ₃₎ 219 4-benzyloxy-C ₆ H ₄ -CH (CH ₃₎ 220 l-naphthyl-CH (CH ₃₎ 221 2-naphthyl-CH (CH ₃₎ 222 9-anthryl-CH (CH ₃₎ 223 2-CH ₃ -3-C ₆ H ₅ OC ₆ H ₃ -CH (CH ₃ ) 224 2-CH ₃ -4-C ₆ H ₅ OC ₆ H ₃ -CH (CH ₃ ) 225 2-CH ₃ -5-C ₆ H ₅ OC ₆ H ₃ -CH (CH ₃ ) 226 3-CH ₃ -4-C ₆ H ₅ OC ₆ H ₃ -CH (CH ₃ ) 227 4-CH ₃ -5-C ₆ H ₅ OC ₆ H ₃ -CH (CH ₃ ) 228 2-Cl-3-C ₆ H ₅ OC ₆ H ₃ -CH (CH ₃ ) 229 2-Cl-4-C ₆ H ₅ OC ₆ H ₃ -CH (CH ₃ ) 230 2-Cl-5-C ₆ H ₅ OC ₆ H ₃ -CH (CH ₃ ) 231 3-Cl-4-C ₆ H ₅ OC ₆ H ₃ -CH (CH ₃ ) 232 3-Cl-5-C ₆ H ₅ OC ₆ H ₃ -CH (CH ₃ ) 233 2-CH ₃ -4-CO ₂ CH ₃ -C ₆ H ₃ -CH (CH ₃ ) 234 2-CH ₃ -5-CO ₂ CH ₃ -C ₆ H ₃ -CH (CH ₃ ) 235 C ₆ ^h 5- ( ^CH 2) 2 236 2-F- ^C 6 H 4 - ( ^c H 2) ₂ 237 3-FC ₆ H ₄ - (CH ₂ ) ₂ 238 4-FC ₆ ^h 4- ( ^ch 2) ₂

Table 2 - continued

21ouč.

number R ² 239 2-Cl-C ₆ H ₄ - (CH _{2) 2} 240 3-Cl-C ₆ H ₄ - (CH _{2) 2} 241 4-Cl-C 8 H ₄ - (CH ₂ ) ₂ 242 2,3-Cl ₂ -C ₆ H ₃ - (CH ₂ ) ₂ 243 2,4-Cl ₂ -C ₈ H ₃ - (CH ₂ ) ₂ 244 2,5-Cl ₂ -C ₆ H ₃ - (CH ₂ ) ₂ 245 2,6-Cl ₂ -C ₆ H ₃ - (CH ₂ ) ₂ 246 3,4-Cl ₂ -C ₆ H ₃ - (CH ₂ ) ₂ 247 2-CH ₃ -C ₆ H ₄ - (CH ₂ ) ₂ 248 3-CH ₃ -C ₆ H ₄ - (CH ₂ ) ₂ 249 4-CH ₃ -C ₆ H ₄ - (CH ₂ ) ₂ 250 2,3- (CH ₃ ) ₂ -C ₆ H ₃ - (CH ₂ ) ₂ 251 2,4- (CH ₃ ) ₂ -C ₆ H ₃ - (CH ₂ ) ₂ 252 2,5- (CH ₃ ) ₂ -C ₆ H ₃ - (CH ₂ ) ₂ 253 3,4- (CH ₃ ) ₂ -C ₆ H ₃ - (CH ₂ ) ₂ 254 3,5- (CH ₃ ) ₂ -C ₆ H ₃ - (CH ₂ ) ₂ 255 4,5- (CH ₃ ) ₂ -C ₆ H ₃ - (CH ₂ ) ₂ 256 2,3,4- (CH ₃ ) ₃ -C ₆ H ₂ - (CH ₂ ) ₂ 257 2,4,5- (CH ₃ ) ₃ -C ₆ H ₂ - (CH ₂ ) ₂ 258 2,4,6- (CH ₃ ) ₃ -C ₆ H ₂ - (CH ₂ ) ₂ 259 2,3,6- (CH ₃ ) ₃ -C ₆ H ₂ - (CH ₂ ) ₂ 260 2-CF ₃ -C ₆ H ₄ - (CH ₂ ) ₂ 261 3-CF ₃ -C ₆ H ₄ - (CH ₂ ) ₂ 262 4-CF ₃ -C ₆ H ₄ - (CH ₂ ) ₂ 263 2-CH ₃ -3-CF ₃ -C ₆ H ₃ - (CH ₂ ) ₂ 264 2-CH ₃ -4-CF ₃ -C ₆ H ₃ - (CH ₂ ) ₂ 265 2-CF ₃ -3-CH ₃ -C ₆ H ₃ - (CH ₂ ) ₂ 266 2-CF ₃ -4-CH ₃ -C ₆ H ₃ - (CH ₂ ) ₂ 267 2-CF ₃ -5-CH ₃ -C ₈ H ₃ - (CH ₂ ) ₂ 268 2-CH ₃ -3-CH ₃ -C ₆ H ₃ - (CH ₂ ) ₂

Table 2 - continued

21ouč.

number R ² 269 2-Br-C ₆ H ₄ - (CH ₂ ) ₂ 270 3-Br-C ₆ H ₄ - (CH ₂ ) ₂ 271 4-Br-C ₆ H ₄ - (CH ₂ ) ₂ 272 2- (2-propyl-C ₆ H ₄ - (CH ₂ ) ₂₎ 273 3-cyclopropyl-CGH from ₄ - (CH _{2) 2} 274 4- (2-propyl-C ₆ H ₄ - (CH ₂ ) ₂₎ 275 _{2-isopropyl-3-C-3} CGH - (CH _{2) 2} 276 2-isopropyl-4-Cl-C ₆ H ₃ - (CH _{2) 2} 277 2-isopropyl-5-Cl-C ₆ H ₃ ~ _{(CH2) 2} 278 2-CH ₃ -3-isopropyl-C ₆ H ₃ - (CH ₂ ) ₂ i 279 2-CH ₃ -4-isopropyl-C 8 H ₃ - (CH ₂ ) ₂ 280 2-CH ₃ -5-isopropyl-C 8 H ₃ - (CH ₂ ) ₂ 281 2-tert-C ₄ H ₉ -C ₆ H ₄ - (CH ₂ ) ₂ 282 3-tert-C ₄ H ₉ -C ₆ H ₄ - (CH ₂ ) ₂ 283 4-tert-C ₄ H ₉ -C ₆ H ₄ - (CH ₂ ) ₂ 284 2-CH ₃ -3-tert-C ₄ H ₉ -C ₆ H ₃ - (CH ₂ ) ₂ 285 2-CH ₃ -4-t-C ₄ H _9, -C _g H ₃ - (CH _{2) 2} 286 2-CH ₃ -5-tert-C ₄ H ₉ -C ₆ H ₃ - (CH ₂ ) ₂ 287 3-CH ₃ -4-tert-C ₄ H ₉ -C ₆ H ₃ - (CH ₂ ) ₂ 288 3-CH ₃ -5-tert-C ₄ H ₉ -C ₆ H ₃ - (CH ₂ ) ₂ 289 2-Cl-3-tert-C ₄ H ₉ -C ₆ H ₃ - (CH ₂ ) ₂ 290 2-Cl-4-tert-C ₄ H ₉ -C ₆ H ₃ - (CH ₂ ) ₂ 291 3-Cl-5-tert-C ₄ H ₉ -C ₆ H ₃ - (CH ₂ ) ₂ 292 3-Cl-4-tert-C ₄ H ₉ -C ₆ H ₃ - (CH ₂ ) ₂ 293 3-Cl-5-tert-C ₄ H ₉ -C ₆ H ₃ - (CH ₂ ) ₂ 294 2-OCH ₃ -C ₆ H ₄ -CH ₂ - (CH ₂ ) ₂ 295 3-OCH ₃ -C ₆ H ₄ -CH ₂ - (CH ₂ ) ₂ 296 4-OCH ₃ -C ₆ H ₄ -CH ₂ - (CH ₂ ) ₂ 297 2-CH ₃ -3-OCH ₃ -C ₆ H ₃ - (CH ₂ ) 2 298 2-CH ₃ -4-OCH ₃ -C ₆ H ₃ - (CH ₂ ) ₂

Table 2 - continued

2ouč.

number R ² 299 2-CH ₃ -5-OCH ₃ -C ₆ H ₃ - (CH ₂ ) ₂ 300 ₍ 3-CH ₃ -4-OCH ₃ -C ₆ H ₃ - (CH ₂ ) ₂ i 301 3-CH ₃ -5-OCH ₃ -C ₆ H ₃ - (CH ₂ ) ₂ 302 2-Cl-3-OCH ₃ -C ₆ H ₃ - (CH ₃ ) ₂ 303 2-Cl-4-OCH ₃ -C ₆ H ₃ - (CH ₃ ) ₂ .304 2-Cl-5-OCH ₃ -C ₆ H ₃ - (CH ₃ ) ₂ 305 2-OCH ₃ -3-Cl-C ₆ H ₃ - (CH ₃ ) ₂ 306 2-OCH ₃ -4-Cl-C ₆ H ₃ - (CH ₃ ) ₂ 307 2-OCH ₃ -5-Cl-C ₆ H ₃ - (CH ₃ ) ₂ 308 2-CH ₃ -4-cyclohexyl-C 8 H ₃ - (CH ₂ ) 2 309 2-CH ₃ -4-C ₆ H ₅ -C ₆ H ₃ - (CH ₂ ) ₂ 310 2-CH ₃ -3-Br-C ₆ H ₃ - (CH ₂ ) ₂ 311 2-CH ₃ -4-Br-C ₆ H ₃ - (CH ₂ ) ₂ 312 2-CH ₃ -5-Br-C ₆ H ₃ - (CH ₂ ) ₂ 313 2-CH ₃ -3- (methoxyiminomethyl) -C ₈ H ₃ - (CH ₂ ) ₂ 314 _{2-methoxyimino-methyl-4} CGH - _{(CH2) 2} 315 _{3-methoxyimino-methyl-4} CGH - _{(CH2) 2} 316 2-CH ₃ -4- (methoxyiminomethyl) -C ₈ H ₃ - (CH ₂ ) ₂ 317 2-phenyl-C ₆ H _4- (CH _{2) 2} 318 3-phenyl-C ₆ H ₄ - (CH _{2) 2} 319 4-phenyl-C ₆ H ₄ - (CH _{2) 2:} 320 _2-phenoxy-4 CGH - (CH _{2) second} 321 _3-phenoxy-4 CGH - _{(CH2) 2} 322 _4-phenoxy-4 CGH - _{(CH2) 2} 323 2-benzyloxy-C 8 H ₄ - (CH ₂ ) 2 324 _{3-benzyloxy-4-a} CGH _{(CH2) 2} 325 _{4-benzyloxy-4-CGH (CH2) 2} 326 l-naphthyl _{(CH2) 2} 327 2-naphthyl- (CH ₂ ) ₂ ? 328 9-anthryl- _{(CH2) 2}

Table 2 - continuation

Zlouč.

number R ² 329 2-CH ₃ -3-C ₆ H ₅ OC ₆ H ₃ - (CH ₂ ) ₂ 330 2CH ₃ -4-C ₆ H ₅ OC ₆ H ₃ - (CH ₂ ) ₂ 331 2-CH ₃ -5-C ₆ H ₅ OC ₆ H ₃ - (CH ₂ ) ₂ 332 3-CH ₃ -4-C ₆ H ₅ OC ₆ H ₃ - (CH ₂ ) ₂ 333 4-CH ₃ -5-C ₆ H ₅ OC ₆ H ₃ - (CH ₂ ) ₂ 334 2-Cl-3-C ₆ H ₅ OC ₆ H ₃ - (CH ₂ ) ₂ 335 2-Cl-4-C ₆ H ₅ OC ₆ H ₃ - (CH ₂ ) ₂ 336 2-Cl-5-C ₆ H ₅ OC ₆ H ₃ - (CH ₂ ) ₂ 337 3-Cl-4-C ₆ H ₅ O-C ₆ H ₃ - (CH ₂ ) ₂ 338 3-Cl-5-C ₆ H ₅ OC ₆ H ₃ - (CH ₂ ) ₂ '339 2-CH ₃ -4-CO ₂ CH ₃ -C ₆ H ₃ - (CH ₂ ) ₂ 340 2-CH ₃ -5-CO ₂ CH ₃ -C ₆ H ₃ - (CH ₂ ) ₂ 341 c ₆ h ₅ -ch = ch-ch ₂ 342 2-FC ₆ H ₄ -CH = CH-CH ₂ 343 3-FC ₆ H ₄ -CH = CH-CH ₂ 344 4-FC ₆ H ₄ -CH = CH-CH ₂ 345 2-ci-c ₆ h ₄ -ch = ch-ch ₂ 346 3-Cl-C 8 H ₄ -CH = CH-CH ₂ 347 4-ci-c ₆ h ₄ -ch = ch-ch ₂ 348 2,3-Cl ₂ -C ₆ H ₃ -CH = CH-CH ₂ 349 2,4-Cl ₂ -C ₆ H ₃ -CH = CH-CH ₂ 350 2,5-Cl ₂ -C ₆ H ₃ tCH = CH-CH ₂ 351 2,6-Cl ₂ -C ₆ H ₃ -CH = CH-CH ₂ 352 3,4-Cl ₂ -C ₆ H ₃ -CH = CH-CH ₂ 353 2-ch ₃ -c ₆ h ₄ -ch = ch-ch ₂ 354 3-ch ₃ -c ₆ h ₄ -ch = ch-ch ₂ 355 4-ch ₃ -c ₆ h ₄ -ch = ch-ch ₂ 356 2,3- (CH ₃ ) ₂ -C ₆ H ₃ -CH = CH-CH ₂ 357 2,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH = CH-CH ₂ 358 2,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH = CH-CH ₂

Table 2 - continued

21ouč.

number R ²

359 3,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH = CH-CH ₂ 360; 1 3,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH = CH-CH ₂ 361 4,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH = CH-CH ₂ 362 2,3,4- (CH ₃ ) ₃ -C ₆ H ₂ -CH = CH-CH 363 2,4,5- (CH ₃ ) ₃ -C ₆ H ₂ -CH = CH-CH 364 2,4,6- (CH ₃ ) ₃ -C ₆ H ₂ -CH = CH-CH 365 2,3,6- (CH ₃ ) ₃ -C ₆ H ₂ -CH = CH-CH 366 2-cf ₃ -c ₆ h ₄ -ch = ch-ch ₂ 367 3-cf ₃ -c ₆ h ₄ -ch = ch-ch ₂ 368 4-cf ₃ -c ₆ h ₄ -ch = ch-ch ₂ 369 2-CH ₃ -3-CF ₃ -C ₆ H ₃ -CH = CH-CH ₂ 370 2-CH ₃ -4-CF ₃ -C ₆ H ₃ -CH = CH-CH ₂ 371 2-CF ₃ -3-CF ₃ -C ₆ H ₃ -CH = CH-CH ₂ 372 2-CF ₃ -4-CF ₃ -C ₆ H ₃ -CH = CH-CH ₂ 373 2-CF ₃ -5-CF ₃ -C ₆ H ₃ -CH = CH-CH ₂ 374 2-CH ₃ -5-CF ₃ -C ₆ H ₃ -CH = CH-CH ₂ 375 ^C 6 ^H 5 - ( ^CH 2) ₃ 376 C ₆ ^h 5 - (C ^h 2) ₄ 377 c ₆ h ₅ -ch ₂ ch = ch-ch ₂ 378 4-F-CH-CH = CH- (CH) ₂ 379 ch ₃ o-what-ch ₂ 380 ch ₃ ch ₂ o-co-co ₂ 381 ch ₃ -co-ch ₂ -ch ₂ 382 t-C ₄ H _g O-CO-CH ₂ 383 tert-C ₄ H _g O-CO- (CH ₂ ) ₂ 384 t-C ₄ H _g O-CO-CH (CH ₃ ) 385 nC ₄ H _g O-CO-CH ₂ 386 C ₄ H ₈ O-CO-CH ₂ 387. nC ₃ H ₇ O-CO-CH ₂ 388 sec.-C ₄ HgO-COCH ₂

Table 2 - continuation

Zlouč.

number R ² 389 ^C 6 ^H 5 - ^C ° - ^CH 2 3S) 0 2-CH ₃ -C ₆ H ₄ O-CO-CH ₂ 391 3-CH ₃ -C ₆ H ₄ O-CO-CH ₂ 392 4-CH ₃ -C ₆ H ₄ O-CO-CH ₂ 393 2-Cl-C 8 H ₄ O-CO-CH ₂ 394 3-Cl-C 8 H ₄ O-CO-CH ₂ 395 4-Cl-CGH ₄ O-CO-CH ₂ 396 ^c g ^H 5 ^-c ( ^CH 3) ^{= CH-CH} 2 397 _(i O'CHj 398 ⁽¹ ft ^ n ^* CH ₂ C1 399 Λ 400

Table 2

21ouč.

number

401

402

403

404

405

406

407

408

409

410

- continuation

CF ₃ ch ₂

F

CH ₂

ch ₂

table

21ouč.

'number

411

412

413

414

415

416

417

418

419

- continuation of them ₂

ch ₃ ch ₃ ch ₃

Cl ch ₂

br

CH ₂ CH ₃ CH ₂

Cl

Cl ch ₂

Table 2 - continued

Zlouč.

number R ²

420

421

422

423

425

426

- continuation

table

2louč.

number

441

442

443

444

445

446

447

448

449

450

451

CH ₂

Table 2 - continued

Zlouč.

number

430

431

432

433

434

435

436

437

438

439

440

- continuation

table

Zlouč.

number

452

453

454

455

456

457

458

459

460

461

Table 2 - continuation / farewell.

number R ²

462 _N-C-CH2

463 tert-C ₄ H ₉ O-CH ₂ -CH = CH-CH ₂

464 (CH ₃ ) ₂ -C =CH-CH ₂ -CH ₂ -C (CH ₃ ) = CH-CH ₂

465 (CH ₃ ) ₂ CH-C = CH-CH ₂ -CH ₂ -C (CH ₃ ) = CH-CH ₂

466 C ₆ H ₅ -O-CH (CH ₃ ) -CH ₂

467 4-Cl-C ₆ H ₄ -O-CH _{(CH3) CH2}

Table 3

10 = c-nhch ₃

Zlouč.

number r! R

1 H H H 2. H ch ₃ H 3 H t-C ₄ H ₉ H 4 H _CH2-CH-CH2 H 5 H CH ₂ = C (C1) -CH ₂ H 6 H CH ₂ = C (CH ₃ ) -CH ₂ H 7 H ch ₃ ch = ch-ch ₂ H 8 H HCsCCH ₂ H 9 H ch ₃ c = c-ch ₂ H 10 H Cyclo-cghj! H 11 H c ₆ h ₅ -ch ₂ H 12 H 2-F-C 8 H ₄ -CH ₂ H 13 H 3-FC ₆ H ₄ -CH ₂ H 14 H 4-F-C 8 ^H 4 ^-CH 2 H 15 H _{2-Cl-4-CH 2} CGH H 16 H 3-Cl-C ₆ H ₄ CH ₂ H 17 H _{4-Cl-4-CH 2} CGH H 18 H 2-Br-C 8 H ₄ -CH ₂ H 19 H 3-Br-C ₆ H ₄ CH ₂ H 20 H 4-Br-C ₆ H ₄ CH ₂ H 21 H 2-CH ₃ -C ₈ H ₄ -CH ₂ H 22 H 3-CH ₃ -C ₈ H ₄ -CH ₂ H 23 H 4-CH ₃ -C ₈ H ₄ -CH ₂ H 24 H 2-CF ₃ ^-c g ^H ₄ ^-CH 2 H 25 H 3-CF ₃ -C ₆ H ₄ -CH ₂ H

Table 3 - continued

Zlouč.

number R ¹ R ² R ' 26 H 4-CF ₃ -C ₆ H ₄ -CH ₂ H 27 H 2-10C ₃ H ₇ -C ₆ H ₄ -CH ₂ H 28 H 3-10C ₃ H ₇ -C ₆ H ₄ -CH ₂ H 29 H 4-10C ₃ H ₇ -C ₆ H ₄ -CH ₂ H 30 H 2-tert-C ₃ H ₇ -C ₈ H ₄ -CH ₂ H 31 H 3-tert-C ₃ H ₇ -C ₆ H ₄ -CH ₂ H 32 H 4-tert-C ₃ H ₇ -C ₆ H ₄ -CH ₂ H 33 H 2-CH ₃ OC ₆ H ₄ -CH ₂ H 34 H 3-CH ₃ OC ₆ H ₄ -CH ₂ H 35 H 4-CH ₃ OC ₆ H ₄ -CH ₂ H 36 H _{2-cyano-4-CH 2} CGH H 37 H _{3-cyano-4-CGH CH2} H 38 H _{4-cyano-4-CGH CH2} H 39 H _{2-nitro-4-CGH CH2} H 40 H _{3-nitro-4-CGH CH2} H 41 H _{4-nitro-4-CGH CH2} H 42 H 2,4-Cl ₂ -C ₆ ^H ₃ -CH ₂ H 43 H 3,4-Cl ₂ -C ₆ H ₃ -CH ₂ H 44 H 3,5-Cl ₂ -C ₈ H ₃ -CH ₂ H 45 H 2,6-Cl ₂ -C ₈ H ₃ -CH ₂ H 46 H 2,4- (CH ₃ ) ₂ -C ₈ H ₃ -CH ₂ H 47 H 2,5- (CH ₃ ) ₂ -C ₈ H ₃ -CH ₂ H 48 H 3,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ H 49 H 3,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ H 50 H _{l-naphthyl-CH2} H 51 H _{2-naphthyl-CH2} H 52 H c ₆ h ₅ -ch (ch ₃ ) H 53 H 2-Cl-CGH ₄ -CH (CH ₃₎ H 54 H 3-Cl-CGH ₄ -CH (CH ₃₎ H 55 H 4-Cl-C ₆ H ₄ -CH (CH ₃ ) H

Table 3 - continued.

Zlouč.

number R ¹ R ² R ' 56 H 2-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) H 57 H 3-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) H 58 H 4-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) H 59 H 2-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) H 60 H 3-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) H 61 H 4-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) H 62 H 2-tert-C ₄ H ₉ -C ₆ H ₄ -CH (CH ₃ ) H 63 H 3-tert-C ₄ H ₉ -C ₆ H ₄ -CH (CH ₃ ) H 64 H 4-tert-C ₄ H ₉ -C ₆ H ₄ -CH (CH ₃ ) H 65 H 2-CH ₃ OC ₆ H ₄ -CH (CH ₃ ) H 66 H 3-CH ₃ OC ₆ H ₄ % H (CH ₃ ) H 67 H 4-CH ₃ OC ₆ H ₄ -CH (CH ₃ ) H 68 H 2-cyano-C ₆ H ₄ -CH (CH ₃₎ H 69 H 3-cyano-C ₆ H ₄ -CH (CH ₃₎ H 70 H 4-cyano-C ₆ H ₄ -CH (CH ₃₎ H 71 H 2,4-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) H 72 H 3,4-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) H 73 H 3,5-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) H 74 H 2,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH (CH ₃ ) H 75 H 2,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH (CH ₃ ) H 76 H ch ₃ ooc-ch ₂ H 77 H C ₂ H ₅ OOC-CH ₂ H 78 H OR-C ₃ H ₇ 00C-CH ₂ H 79 H tert-C ₄ H ₉ OOC-CH ₂ H 80 H tert-C ₄ H ₉ OOC-CH (CH ₃ ) H 81 H _NSC-CH2 H 82 H C ₆ H ₅ ^{C H} 2 C ° H 83 H pyridin-2-ylmethyl H 84 H pyrazin-2-ylmethyl H 85 H pyrimidin-2-ylmethyl H

Table 3 - continued

Zlouč.

number R ¹ R ² r ' 86 H fur-2-ylmethy1 H 87 H pyrrol-2-ylmethyl H 88 H N-methylpyrrole-2-ylmethyl H 89 H thien-2-ylmethyl H 90 H i.oxazol-5-ylmethyl H 91 H thiazol-2-ylmethyl H 92 H thiazol-5-ylmethyl H 93 H oxazol-2-ylmethyl H 94 H pyrazol-3-ylmethyl H 95 H benzofuran-2-ylmethyl H 96 H indol-2-ylmethyl H 97 H indol-3-ylmethyl H 98 H benzothiazol-2-ylmethyl H 99 H quinolin-2-ylmethyl H 100 H 4-ci-c ₆ h ₄ and (ch ₃ ) -ch ₂ H 101 ch ₃ H H 102 ch ₃ ch ₃ H 103 ch ₃ t-C ₄ H _g H 104 ch ₃ ch ₂ = ch-ch ₂ H 105 ch ₃ CH ₂ = C (C1) -CH ₂ H 106 ch ₃ CH ₂ = C (CH ₃ ) -CH ₂ H 107 ch ₃ ch ₃ ch = ch-ch ₂ H 108 ch ₃ hc = cch ₂ H 109 ch ₃ CH ₃ C = C-CH ₂ - H 110 ch ₃ Cyclo-cghj! H 111 ch ₃ C ₆ H ₅ - ^CH 2 H 112 ch ₃ 2-FC ₆ H ₄ -CH ₂ H 113 ch ₃ 3-FC ₆ H ₄ -CH ₂ H 114 ch ₃ 4-FC ₆ H ₄ -CH ₂ H 115 ch ₃ 2-Cl-C ₆ H ₄ CH ₂ H

Table 3 - continued

21ouč.

number R ¹ R ² r ' 116 ch ₃ 3-Cl-C ₆ H ₄ CH ₂ H 117 ch ₃ 4-Cl-C ₆ H ₄ CH ₂ H 118 ch ₃ 2-Br-C ₆ H ₄ CH ₂ H 119 ch ₃ 3-Br-C ₆ H ₄ CH ₂ H 120 ch ₃ 4-Br-C ₆ H ₄ CH ₂ H 121 ch ₃ 2-CH ₃ -C ₆ H ₄ -CH ₂ H 122 ch ₃ 3-CH ₃ -C ₆ H ₄ -CH ₂ H 123 ch ₃ 4-CH ₃ -C ₆ H ₄ -CH ₂ H 124 ch ₃ 2-CF ₃ -C ₆ H ₄ -CH ₂ H 125 ch ₃ 3-CF ₃ ^-C 6 ^H 4 ^-CH ₂ H 126 ch ₃ 4-CF ₃ -C ₆ H ₄ -CH ₂ H 127 ch ₃ 2-Z 2 C ₃ H ₇ -C ₆ H ₄ -CH ₂ H 128 ch ₃ 3-iso-C ₃ H ₇ -C ₆ H ₄ -CH ₂ H 129 ch ₃ 4-O-C ₃ H ₇ -C ₆ H ₄ -CH ₂ H 130 ch ₃ 2-tert-C ₄ H 8 -C 8 H ₄ -CH ₂ H 131 ch ₃ 3-tert-C ₄ H ₉ -C ₆ H ₄ -CH ₂ H 132 ch ₃ 4-tert-C ₄ H ₉ -C ₆ H ₄ -CH ₂ H 133 ch ₃ 2-CH ₃ OC ₆ H ₄ -CH ₂ H 134 ch ₃ 3-CH ₃ OC ₆ H ₄ -CH ₂ H 135 ch ₃ 4-CH ₃ OC ₆ H ₄ -CH ₂ H 136 ch ₃ 2-cyano-C ₆ H ₄ -CH ₂ H 137 ch _{3 3-cyano-4-CGH CH2} H 138 ch _{3 4-cyano-4-CH 2} CGH H 139 ch ₃ 2-nitro-C ₆ H ₄ CH ₂ H 140 ch _{3 3-nitro-4-CH 2} CGH H 141 ch ₃ 4-nitro-C ₆ H ₄ CH ₂ H 142 ch ₃ 2,4-Cl ₂ ^-C 6 ^H ₃ ^-CH 2 H 143 ch ₃ 3,4-C 1 _2-C ^3-C ₆ H 2 ^hours H 144 ch ₃ 3,5-Cl ₂ -C ₆ H ₃ -CH ₂ H 145 ch ₃ 2,6-Cl ₂ ^-C 6 ^H 3-C ^H 2 H

Table 3 - continued

Zlouč.

number R ¹ R ² R ' 146 ch ₃ 2,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ H 147 ch ₃ 2,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ H 148 ch ₃ 3,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ H 149 ch ₃ 3,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ H 150 ch _{3 l-naphthyl-CH2} H 151 ch _{3 2-naphthyl-CH2} H 152 ch ₃ C ₆ H ₅ -CH (CH ₃ ) H 153 ch ₃ 2-Cl-C ₆ H ₄ -CH (CH ₃₎ H 154 ch ₃ 3-Cl-C ₆ H ₄ -CH (CH ₃₎ H 155 ch ₃ 4-Cl-C ₆ H ₄ -CH (CH ₃ ) H 156 ch ₃ 2-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) H 157 ch ₃ 3-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) H 158 ch ₃ 4 'CH ₃ -C ₆ H ₄ -CH (CH ₃ ) H 159 ch ₃ 2-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) H 160 ch ₃ 3-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) H 161 ch ₃ 4-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) H 162 ch ₃ 2-tert-C ₄ H ₉ -C ₆ H ₄ -CH (CH ₃ ) H 163 ch ₃ 3-tert-C ₄ H _g -C ₆ H ₄ -CH (CH ₃ ) H 164 ch ₃ 4-tert-C ₄ H _g -C ₆ H ₄ -CH (CH ₃ ) H 165 ch ₃ 2-CH ₃ OC ₆ H ₄ -CH (CH ₃ ) H 166 ch ₃ 3-CH ₃ OC ₆ H ₄ -CH (CH ₃ ) H 167 ch ₃ 4-CH ₃ OC ₆ H ₄ -CH (CH ₃ ) H 168 ch ₃ 2-cyano-C ₆ H ₄ -CH (CH ₃₎ H 169 ch ₃ 3-cyano-CGH ₄ -CH (CH ₃₎ H 170 ch ₃ 4-cyano-CGH ₄ -CH (CH ₃₎ H 171 ^CH 3 2,4-Cl ₂ -C ₈ H ₃ -CH (CH ₃ ) H 172 ch ₃ 3,4-Cl ₂ -C ₈ H ₃ -CH (CH ₃ ) H 173 ch ₃ 3,5-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) H 174 ch ₃ 2,4- (CH ₃ ) ₂ -C ₈ H ₃ -CH (CH ₃ ) H 175 ch ₃ 2,5- (CH ₃ ) ₂ -C ₈ H ₃ -CH (CH ₃ ) H

Table 3 - continued

Zlouč.

number R ¹ R ² R ⁶ 176 ^CH 3 ch ₃ ooc-ch ₂ H 177 ch ₃ c ₂ h ₅ ooc-ch ₂ H 178 ch ₃ ISO-C ₃ H ₇ OOC-CH ₂ H 179 ch ₃ t-C ₄ H _g 00C-CH ₂ H 180 ch ₃ tert-C ₄ HgOOC-CH (CH ₃ ) H 181 ch _{3 NSC-CH2} H 182 ch ₃ c ₆ h ₅ co-ch ₂ H 183 ch ₃ pyridin-2-ylmethyl H 184 ch ₃ pyrazin-2-ylmethyl H 185 ch ₃ pyrimidin-2-ylmethyl H 186 ch ₃ fur-2-ylmethyl H 187 ch ₃ pyrrol-2-ylmethyl H 188 ch ₃ N-methylpyrrole-2-ylmethyl H 189 ch ₃ thien-2-ylmethyl H 190 ch ₃ isoxazol-5-ylmethyl H 191 ch ₃ thiazol-2-ylmethyl H 192 ch ₃ thiazol-5-ylmethyl H 193 ch ₃ oxazol-2-ylmethyl H 194 ch ₃ pyrazol-3-ylmethyl H 195 ch ₃ benzofuran-2-ylmethyl H 196 gh ₃ indol-2-ylmethyl H 197 ch ₃ indol-3-ylmethyl H 198 ch ₃ benzothiazol-2-ylmethyl H 199 ch ₃ quinolin-2-ylmethyl H 200 ch ₃ 4-Cl-C 8 H ₄ OCH (CH ₃ ) -CH ₂ H 201 H H ch ₃ 202 H ch ₃ ch ₃ 203 H t-c ₄ H ₉ ch ₃ 204 H ch ₂ = ch-ch ₂ ch ₃ 205 H CH ₂ = C (C1) -CH ₂ ch ₃

Table 3 - continued

Zlouč.

number R ¹ R ² R ⁶ 206 H ch ₂ = c (ch ₃ ) -ch ₂ ch ₃ 207 H ch ₃ ch = ch-ch ₂ ch ₃ 208 H hcscch ₂ ch ₃ 209 H ch ₃ oc-ch ₂ ch ₃ 210 H cyclo-C ₆ H ₁₁ ch ₃ 211 H ^C 6 ^H 5 ^-CH 2 ^CH 3 212 H 2-FC ₆ H ₄ -CH ₂ ch ₃ 213 H ³ -F- ^C 6 ^H 4 ' ^CH 2 ch ₃ 214 H 4-FC ₆ H ₄ -CH ₂ ch ₃ 215 H 2-Cl-C ₆ H ₄ CH ₂ ch ₃ 216 H 3-Cl-C ₆ H ₄ CH ₂ W ch ₃ 217 H 4-Cl-C ₆ H ₄ CH ₂ ch ₃ 218 H 2-Br-C ₆ H ₄ CH ₂ ch ₃ 219 H 3-Br-C ₆ H ₄ CH ₂ ch ₃ 220 H 4-Br-C ₆ H ₄ CH ₂ ^CH 3 221 H 2-CH ₃ -C ₆ H ₄ -CH ₂ ch ₃ 222 H 3-CH ₃ -C ₆ H ₄ -CH ₂ ch ₃ 223 H 4-CH ₃ -C ₆ H ₄ -CH ₂ ch ₃ 224 H 2-CF ₃ -C ₆ H ₄ -CH ₂ ch ₃ 225 H 3-CF ₃ ^-C 6 ^H 4 ^-CH 2 ^CH 3 226 H 4-CF ₃ -C ₆ H ₄ -CH ₂ ^CH 3 227 H 2 = i? C ₃ H ₇ -C ₆ H ₄ CH ₂ ' ch ₃ 228 H 3-Iso-C ₃ H ₇ -C ₆ H ₄ -CH ₂ ch ₃ 229 H 4 "120-C ₃ H" C ₈ H 4 "CH 2 ch ₃ 230 H 2-tert-C ₄ H ₉ -C ₆ H ₄ -CH ₂ ch ₃ 231 H 3-tert-C ₄ H ₉ -C ₆ H ₄ -CH ₂ ch ₃ 232 H 4-t-C ₄ H _g C ₆ H ₄ CH ₂ ch ₃ 233 H 2-CH ₃ OC ₆ H ₄ -CH ₂ ch ₃ 234 H 3-CH ₃ OC ₆ H ₄ -CH ₂ ch ₃ 235 H 4-CH ₃ OC ₆ H ₄ -CH ₂ ch ₃

Table 3 - continued

Zlouč.

number R ¹ R ² R ⁶ 236 H _{2-cyano-4-CH 2} CGH ch ₃ 237 H 3-cyano-C ₆ H ₄ CH ₂ ch ₃ 238 H 4-cyano-C ₆ H ₄ CH ₂ ch ₃ 239 H 2-nitro-C ₆ H ₄ CH ₂ ch ₃ 240 H _{3-nitro-4-CH 2} CGH ch ₃ 241 H 4-nitro-C ₆ H ₄ CH ₂ ch ₃ 242 H 2,4-Cl ₂ -C ₆ H ₃ -C ^H ₂ ch ₃ 243 H 3,4-Cl ₂ -C ₆ H ₃ -CH ₂ ch ₃ 244 H 3,5-Cl ₂ -C ₈ H ₃ -CH ₂ ch ₃ 245 H 2,6-Cl ₂ -C ₈ H ₃ -CH ₂ ch ₃ 246 H 2,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ ch ₃ 247 H 2,5- (CH ₃ ) ₂ -C ₈ H _{3 -.} CH ₂ ch ₃ 248 H 3,4- (CH ₃ ) ₂ -C ₈ H ₃ -CH ₂ ch ₃ 249 H 3,5- (CH ₃ ) ₂ -C ₈ H ₃ -CH ₂ ch ₃ 250 H _{l-naphthyl-CH2} ch ₃ 251 H _{2-naphthyl-CH2} ch ₃ 252 H c ₆ h ₅ -ch (ch ₃ ) ch ₃ 253 H 2-Cl-C ₆ H ₄ -CH (CH ₃₎ ch ₃ 254 H 3-Cl-CGH ₄ -CH (CH ₃₎ ch ₃ 255 H 4-Cl-CGH ₄ -CH (CH ₃₎ ch ₃ 256 H 2-CH ₃ -C ₈ H ₄ -CH (CH ₃ ) ch ₃ 257 H 3-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) ch ₃ 258 H 4-CH ₃ -C ₈ H ₄ -CH (CH ₃ ) ch ₃ 259 H 2-CF ₃ -C ₈ H ₄ -CH (CH ₃ ) ch ₃ 260 H 3-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) ch ₃ 261 H 4-CF ₃ -C ₈ H ₄ -CH (CH ₃ ) ch ₃ 262 H 2-tert-C ₄ H ₉ -C ₈ H ₄ -CH (CH ₃ ) ch ₃ 263 H 3-tert-C ₄ H ₉ -C ₆ H ₄ -CH (CH ₃ ) ch ₃ 264 H 4-t-C ₄ H _g -CgH ₄ -CH (CH ₃₎ ch ₃ 265 H 2-CH ₃ O-C ₈ H ₄ -CH (CH ₃ ) ch ₃

Table 3 - continued

Zlouč.

number R ¹ R ² R ⁶ 266 H 3-CH ₃ O-C ₆ H ₄ -CH (CH ₃ ) ch ₃ 267 1 H 4-CH ₃ OC ₆ H ₄ -CH (CH ₃ ) ch ₃ 268 H 2-cyano-C ₆ H ₄ -CH (CH ₃₎ ch ₃ 269 H 3-cyano-C ₆ H ₄ -CH (CH ₃₎ ch ₃ 270 H 4-cyano-C ₆ H ₄ -CH (CH ₃₎ ch ₃ 271 H 2,4-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) ch ₃ 272 H 3,4-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) ch ₃ 273 H 3,5-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) ch ₃ 274 H 2,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH (CH ₃ ) ch ₃ 275 H 2,5- (CH ₃ ) ₂ -C ₈ H ₃ -CH (CH ₃ ) ch ₃ \ 276 H ch ₃ ooc-ch ₂ ch ₃ 277 H C ₂ H ₅ OOC-CH ₂ ch ₃ 278 H iso-C ₃ H ₂ OOC-CH ₂ ch ₃ 279 H tert-C ₄ H _g 00C-CH ₂ ch ₃ 280 H tert-C ₄ HgOOC-CH (CH ₃ ) ^CH 3 281 H n = c — ch ₂ ch ₃ 282 H ^C 6 ^H 5 ^C ° ^-CH 2 ch ₃ 283 H pyridin-2-ylmethyl ch ₃ 284 H pyrazin-2-ylmethyl ch ₃ 285 H pyrimidin-2-ylmethyl ch ₃ 286 H fur-2-ylmethyl _; ch ₃ 287 H pyrrole-2-ylmethy1 ch ₃ 288 H N-methylpyrrole-2-ylmethyl ch ₃ 289 H thien-2-ylmethyl ch ₃ 290 H i, oxazol-5-ylmethyl ch ₃ 291 H thiazol-2-ylmethyl ch ₃ 292 H thiazol-5-ylmethyl ch ₃ 293 H oxazol-2-ylmethyl ch ₃ 294 H pyrazol-3-ylmethyl ch ₃ 295 H benzofuran-2-ylmethyl ch ₃

Table 3 - continued

Zlouč.

number R ¹ R ² R ⁶ 296 H indol-2-ylmethyl ch ₃ 297 IN indo1-3-ylmethy1 ch ₃ 298 H benzothiazol-2-ylmethyl ch ₃ 299 H quinolin-2-ylmethyl ch ₃ 300 H 4-ci-c ₆ h ₄ and (ch ₃ ) -ch ₂ ch ₃ 301 ch ₃ H ch ₃ 302 ch ₃ ch ₃ ch ₃ 303 ch ₃ t-C ₄ H ₉ ch ₃ 304 ch ₃ ch ₂ = ch-ch ₂ ch ₃ 305 ch ₃ ch ₂ = c (ci) -ch ₂ ch ₃ 306 ch ₃ ' ch ₂ = c (ch ₃ ) -ch ₂ ch ₃ 307 ch ₃ CH ₃ CH = CH-CH ₂ ch ₃ 308 ch ₃ HCsCCH ₂ ch ₃ 309 ch ₃ ch ₃ c = c-ch ₂ ch ₃ 310 ch ₃ cycloalkyl CGH ^^ ch ₃ 311 ch ₃ c ₆ h ₅ -ch ₂ ch ₃ 312 ch ₃ 2-FC ₆ H ₄ -CH ₂ ch ₃ 313 ch ₃ 3-FC ₆ H ₄ -CH ₂ ch ₃ 314 ch ₃ 4-FC ₆ H ₄ -CH ₂ ch ₃ 315 ch ₃ 2-Cl-C ₆ H ₄ CH ₂ 3-Cl-C ₆ H ₄ -CH _2; ch ₃ 316 ch ₃ ch ₃ 317 ch ₃ 4-Cl-C ₆ H ₄ CH ₂ ch ₃ 318 ch ₃ 2-Br-C ₆ H ₄ CH ₂ ch ₃ 319 ch ₃ 3-Br-C ₆ H ₄ CH ₂ ch ₃ 320 ch ₃ 4-Br-C ₆ H ₄ CH ₂ ch ₃ 321 ch ₃ 2-CH ₃ -C ₆ H ₄ -CH ₂ ch ₃ 322 ch ₃ 3-CH ₃ -C ₆ H ₄ -CH ₂ ch ₃ 323 ch ₃ 4-CH ₃ -C ₆ H ₄ -CH ₂ ch ₃ 3 24 ch ₃ 2-CF ₃ -C ₆ ^h 4 ^-c H 2 ch ₃ 325 ch ₃ 3-CF ₃ ^-C 6 ^H 4 ^CH 2 ch ₃

Table 3 - continued

Zlouč.

number R ¹ R ² R ⁶ 326 ch ₃ 4-CF ₃ -C ₆ H ₄ -CH ₂ ch ₃ 327 ch ₃ 2- (2Z, C ₃ H ₇ -C ₆ H ₄ -CH ₂₎ ch ₃ 328 ch ₃ 3-iso-C ₃ H ₇ -C ₆ H ₄ 'CH ₂ ch ₃ 329 ch ₃ 4-iso-C ₃ H ₇ -C ₆ H ₄ -CH ₂ ch ₃ 330 ch ₃ 2-t-C ₄ H _{g 4 -CH2} -CgH ch ₃ 331 ch ₃ 3-t-C ₄ H _g C ₆ H _{4 "CH2} ch ₃ 332 ch ₃ 4-t-C ₄ H _{g 4 -CH2} -CgH ch ₃ 333 ch ₃ 2-CH ₃ OC ₆ H ₄ -CH ₂ ch ₃ 334 ch ₃ 3-CH ₃ OC ₆ H ₄ -CH ₂ ^CH 3 335 ch ₃ 4-CH ₃ OC ₆ H ₄ -CH ₂ ch ₃ 336 ch ₃ 2-cyano-C ₆ H ₄ CH ₂ ch ₃ 337 ch _{3 3-cyano-4-CH 2} CGH ch ₃ 338 ch ₃ 4-cyano-C ₆ H ₄ CH ₂ ch ₃ 339 ch ₃ 2-nitro-C ₆ H ₄ CH ₂ ch ₃ 340 ch _{3 3-nitro-4-CH 2} CGH ch ₃ 341 ch ₃ 4-nitro-C ₆ H ₄ CH ₂ ch ₃ 342 ch ₃ 2,4-Cl ₂ -C ₆ H ₃ -CH ₂ ch ₃ 343 ch ₃ 3,4-Cl ₂ -C ₆ H ₃ -CH ₂ ch ₃ 344 ch ₃ 3,5-Cl ₂ -C ₆ H ₃ -CH ₂ ch ₃ 345 ch ₃ 2,6-Cl ₂ -C ₈ H ₃ -CH ₂ ^CH 3 346 ch ₃ 2,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ ch ₃ 347 ch ₃ 2,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ ch ₃ 348 ch ₃ 3,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ ch ₃ 349 ch ₃ 3,5- (CH ₃ ) ₂ 'C ₆ H ₃ -CH ₂ ch ₃ 350 ch _{3 l-naphthyl-CH2} ch ₃ 351 ch _{3 2-naphthyl-CH2} ch ₃ 352 ch ₃ c ₆ h ₅ -ch (ch ₃ ) ch ₃ 353 ch ₃ 2-Cl-C ₆ H ₄ -CH _(CH3) ch ₃ 354 ch ₃ 3-Cl-C ₆ H ₄ -CH (CH ₃₎ ch ₃ 355 ch ₃ 4-Cl-C ₆ H ₄ -CH (CH ₃ ) ch ₃

Table 3 continued

Zlouč.

number R ¹ R ² R ⁶ 356 ch ₃ 2-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) ch ₃ 357 ? ^H 3 3-CH ₃ -C ₁₆ H ₄ -CH (CH ₃ ) ch ₃ 358 čh ₃ 4-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) ch ₃ 359 ch ₃ 2-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) ch ₃ 360 ch ₃ 3-CF ₃ -C ₈ H ₄ -CH (CH ₃ ) ch ₃ 361 ch ₃ 4-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) ch ₃ 362 ch ₃ 2-tert-C ₄ H ₉ -C ₆ H ₄ -CH (CH ₃ ) ch ₃ 363 ch ₃ 3-tert-C ₄ H _g -C ₆ H ₄ -CH (CH ₃ ) ch ₃ 364 ch ₃ 4-tert-C ₄ H ₉ -C ₆ H ₄ -CH (CH ₃ ) ch ₃ 365 ch ₃ 2-CH ₃ OC ₆ H ₄ -CH (CH ₃ ) ch ₃ 366 ch ₃ v 3-CH ₃ OC ₆ H ₄ -CH (CH ₃ ) ch ₃ 367 ^CH 3 4-CH ₃ OC ₆ H ₄ -CH (CH ₃ ) ch ₃ 368 ch ₃ 2-cyano-C ₆ H ₄ -CH (CH ₃₎ ch ₃ 369 ch ₃ 3-cyano-C ₆ H ₄ -CH (CH ₃₎ ch ₃ 370 ch ₃ 4-cyano-CGH ₄ -CH (CH ₃₎ ch ₃ 371 ch ₃ 2,4-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) ch ₃ 372 ch ₃ 3,4-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) ch ₃ 373 ch ₃ 3,5-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) ch ₃ 374 ch ₃ 2,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH (CH ₃ ) ch ₃ 375 ch ₃ 2,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH (CH ₃ ) ch ₃ 376 ch ₃ ch ₃ ooc-ch ₂ ch ₃ 377 ch ₃ C ₂ H ₅ OOC-CH ₂ ch ₃ 378 ch ₃ IsO-C ₃ H ₇ OOC-CH ₂ ch ₃ 379 ch ₃ tert-C ₄ H ₉ OOC-CH ₂ ch ₃ 380 ch ₃ t-C ₄ H _g 00C-CH (CH ₃ ) ch ₃ 381 ch _{3 NSC-CH2} ch ₃ 382 ch ₃ c ₆ h ₅ co-ch ₂ ch ₃ 383 ch ₃ pyridin-2-ylmethyl ch ₃ 384 ; CH ₃ pyrazin-2-ylmethyl ch ₃ 385 ch ₃ pyrimidin-2-ylmethyl ch ₃

Table 3 - continued

Zlouč.

number R ¹ R ² R ⁶ 386 ch ₃ fur-2-ylmethyl - ^OBJECTIVE 3 387 ch ₃ pyrrol-2-ylmethyl ch ₃ 388 ch ₃ N-ylmethy1 methylpyrro1-2 ch ₃ 389 ch ₃ thien-2-ylmethyl ch ₃ 390 ch ₃ oxazol-5-ylmethyl ch ₃ 391 ^CH 3 thiazol-2-ylmethyl ^CH 3 392 ch ₃ thiazol-5-ylmethyl ch ₃ 393 ch ₃ oxazol-2-ylmethyl ch ₃ 394 ch ₃ pyrazol-3-ylmethyl ch ₃ 395 ch ₃ benzofuran-2-ylmethyl ch ₃ 396 ch ₃ indol-2-ylmethyl ch ₃ 397 ch ₃ indol-3-ylmethyl ch ₃ 398 ch ₃ benzothiazol-2-ylmethyl ch ₃ 399 ch ₃ quinolin-2-ylmethyl ch ₃ 400 ^CH 3 4-ci-c ₆ h ₄ and (ch ₃ ) -ch ₂ ch ₃

Table 4

O-C-NHR ⁴

number R ¹ R ² R ' 1 H H H 2 H ch ₃ H 3 H t-C ₄ H _g H 4 H ch ₂ = ch-ch ₂ H 5 H CH ₂ = C (C1) -CH ₂ H 6 H ch ₂ = c (ch ₃ ) -ch ₂ H 7 H ch ₃ ch = ch-ch ₂ H 8 H hocch ₂ H 9 H CH ₃ CsC-CH ₂ • H 10 H Cyclo-cghj-L H 11 H c ₆ h ₅ - ^ch ₂ H 12 H 2-FC ₆ H ₄ -CH ₂ H 13 H 3-F- ^c ₆ H ₄ ^-CH 2 H 14 H 4-fc ₆ h ₄ -ch ₂ H 15 H 2-Cl-C ₆ H ₄ CH ₂ H 16 H 3-ci-c ₆ h ₄ -ch ₂ H 17 H 4-Cl-C ₆ H ₄ -CH ₂ H 18 H 2-Br-C ₆ H ₄ CH ₂ H 19 H 3-Br-C ₆ H ₄ CH ₂ H 20 H 4-Br-C 8 H ₄ -CH ₂ H 21 H 2-CH ₃ -C ₆ H ₄ -CH ₂ H 22 H 3-CH ₃ -C ₈ H ₄ -CH ₂ H 23 H 4-CH ₃ -C ₈ H ₄ -CH ₂ H 24 H 2-CF ₃ -C ₈ H ₄ -CH ₂ H

Table 4 - continued

Bile.

number R ¹ R ²

25 H 3-CF ₃ ^-C 6 ^H 4 ^CH 2 H 26 H 4-CF ₃ -C ₆ H ₄ -CH _{2 (} H 27 H 2-oC ₃ H _? -C ₆ H ₄ -CH ₂ ' H 28 H 3-ISO-C ₃ H ₇ -C ₆ H ₄ -CH ₂ H 29 H 4-iso-C ₃ H ₇ -C ₆ H ₄ -CH ₂ H 30 H 2-tert-C ₃ H ₇ -C ₆ H ₄ -CH ₂ i ^H 31 H 3-tert-C ₃ H ₇ -C ₆ H ₄ -CH ₂ ^! H 32 H 4-tert-C ₃ H ₇ -C ₆ H ₄ -CH ₂ H 33 H 2-CH ₃ OC ₆ H ₄ -CH ₂ H 34 H 3-CH ₃ OC ₆ H ₄ -CH ₂ H 35 < ' H 4-CH ₃ OC ₆ H ₄ -CH ₂ H 36 H _{2-cyano-4-CH 2} CGH H 37 H _{3-cyano-4-CH 2} CGH H 38 H 4-cyano-C ₆ H ₄ CH ₂ H 39 H _{2-nitro-4-CGH CH2} H 40 H 3-nitro-C ₆ H ₄ CH ₂ H 41 H 4-nitro-C ₆ H ₄ CH ₂ H 42 H 2,4-Cl ₂ -C ₆ H ₃ -CH ₂ H 43 H 3/4-Cl ₂ -C ₆ H ₃ -CH ₂ H 44 H _3/5 Cl ₂ C ₆ H ₃ CH ₂ H 45 H 2,6-Cl ₂ -C ₆ H ₃ -CH ₂ H 46 H 2,4- (CH ₃ ) ₂ -C ₆ H ₃ -rCH ₂ H 47 H 2,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ H 48 H 3,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ H 49 H 3,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ H 50 H _{l-naphthyl-CH2} H 51 H _{2-naphthyl-CH2} H 52 H c ₆ h ₅ -ch (ch ₃ ) H 53 H 2-Cl-C ₆ H ₄ -CH (CH _3); H 54 H , 3-Cl-C ₆ H ₄ -CH (CH ₃₎ H

Table 4 - continued

Bile.

number R ¹ R ² R ' 55 H 4-Cl-C ₆ H ₄ -CH (CH ₃ ) H 56 H 1 2-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) H 57 H 3-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) H 58 H 4-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) H 59 H 2-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) H 60 H 3-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) H 61 H 4-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) H 62 H 2-tert-C ₄ H ₉ -C ₆ H ₄ -CH (CH ₃ ) H 63 H 3-tert-C ₄ H ₉ -C ₆ H ₄ -CH (CH ₃ ) H 64 H 4-tert-C ₄ H ₉ -C ₆ H ₄ -CH (CH ₃ ) H 65 H 2-CH ₃ OC ₆ H ₄ CH (CH ₃ ) H 66 H ' 3-CH ₃ OC ₆ H ₄ -CH (CH ₃ ) H 67 H 4-CH ₃ OC ₆ H ₄ -CH (CH ₃ ) H 68 H 2-cyano-C ₆ H ₄ -CH (CH ₃₎ H 69 H 3-cyano-C ₆ H ₄ -CH (CH ₃₎ H 70 H 4-cyano-C ₆ H ₄ -CH (CH ₃₎ H 71 H 2,4-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) H 72 H 3,4-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) H 73 H 3,5-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) H 74 H 2,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH (CH ₃ ) H 75 H 2,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH (CH ₃ ) H 76 H CH ₃ OOC-CH ₂ ; H 77 H c ₂ h ₅ ooc-ch ₂ H 78 H i-c ₃ h ₇ ooc-ch ₂ H 79 H tert-C ₄ H ₉ OOC-CH ₂ H 80 H tert-C ₄ H _g OOC-CH (CH ₃ ) H 81 H _NSC-CH2 H 82 H c ₆ h ₅ co-ch ₂ H 83 ^H pyridin-2-ylmethyl H 84 H pyrazin-2-ylmethyl H

Table 4 - continued

Bile.

number R ¹ R ²

R ⁴

85 H pyrimidin-2-ylmethyl H 86 H fur-2-ylmethyl H 87 H pyrrol-2-ylmethyl H 88 H N-methylpyrrole-2-ylmethyl H 89 H thien-2-ylmethyl H 90 H isoxazol-5-ylmethyl H 91 H thiazol-2-ylmethyl H 92 H thiazol-5-ylmethyl H 93 H oxazol-2-ylmethyl H 94 H pyrazol-3-ylmethyl H 95 H benzofuran-2-yíiiiethyl H 96 H indol-2-ylmethyl H 97 H indol-3-ylmethyl H 98 H benzothiazol-2-ylmethyl H 99 H quinolin-2-ylmethyl H 100 H 4-ci-c ₆ h ₄ and (ch ₃ ) -ch ₂ H 101 ch ₃ H H 102 ch ₃ ch ₃ H 103 ch ₃ t-C ₄ H _g H 104 ch ₃ ch ₂ = ch-ch ₂ H 105 ch ₃ CH ₂ = C (C1) -CH ₂ H 106 ch ₃ CH ₂ = C (CH ₃ ) -CH ₂ H 107 ch ₃ ch ₃ ch = ch-ch ₂ H 108 ch ₃ HCsCCH ₂ H 109 ch ₃ CH ₃ Cs = C-CH ₂ H 110 ch ₃ cyclo-C ^ H ^ H 111 ch ₃ ^C 6 ^H 5 ^CH 2 H 112 ch ₃ 2-FC ₆ H ₄ -CH ₂ H 113 ch ₃ 3-F- ^C 6 ^H ₄ ^-CH 2 H 114 ch ₃ 4-FC ₆ ^h ₄ - ^CH 2 H

Table 4 - continued

Bile.

number R ¹ R ²

R ⁴

115 ch ₃ 2-Cl-C ₆ H ₄ CH ₂ H 116 ch ₃ 3-Cl-C ₆ H ₄ -CH _{2 (} H 117 ch ₃ 4-Cl-C ₆ H ₄ CH ₂ H 118 ch ₃ 2-Br-C ₆ H ₄ CH ₂ H 119 ch ₃ 3-Br-C ₆ H ₄ CH ₂ H 120 ch ₃ 4-Br-C ₆ H ₄ CH ₂ H 121 ch ₃ 2-CH ₃ -C ₈ H ₄ -CH ₂ H 122 ch ₃ 3-CH ₃ -C ₈ H ₄ -CH ₂ H 123 ch ₃ 4-CH ₃ ^-C 6 ^H 4 ^-ch ₂ H 124 ch ₃ 2-CF ₃ -C ₆ H ₄ -CH ₂ H 125 ch ₃ 3-CF ₃ -C ₆ H ₄ -CH ₂ ·? H 126 ch ₃ 4-CF ₃ -C ₈ H ₄ -CH ₂ H 127 ch ₃ 2-OC ₃ H ₇ -C ₆ H ₄ -CH ₂ H 128 ch ₃ 3-O-C ₃ H ₇ -C ₈ H ₄ -CH ₂ H 129 ch ₃ 4-OC ₃ H ₇ -C ₆ H ₄ -CH ₂ H 130 ch ₃ 2-tert-C ₄ H ₉ -C ₆ H ₄ -CH ₂ H 131 ch ₃ 3-tert-C ₄ H ₉ -C ₈ H ₄ -CH ₂ H 132 ch ₃ 4-tert-C ₄ H ₉ -C ₆ H ₄ -CH ₂ H 133 ch ₃ 2-CH ₃ O-C ₈ H ₄ -CH ₂ H 134 ch ₃ 3-CH ₃ O-C ₈ H ₄ -CH ₂ H 135 ch ₃ 4-CH ₃ OC ₆ H ₄ -CH ₂ H 136 ch _{3 2-cyano-4-CH 2} CGH H 137 ch _{3 3-cyano-4-CH 2} CGH H 138 ch _{3 4-cyano-4-CGH CH2} H 139 ch _{3 2-nitro-4-CH 2} CGH H 140 ch _{3 3-nitro-4-CH 2} CGH H 141 ch _{3 4-nitro-4-CH 2} CGH H 142 ch ₃ 2,4-Cl ₂ -C ₆ H ₃ -CH ₂ H 143 ch ₃ ^3-4 - ^{C1 2-C} 6 ^H 3 ^CH 2 H 144 ch ₃ 3,5-Cl ₂ -C ₆ H ₃ -CH ₂ H

Table 4 - continued

Key, number

145 ch ₃ 2,6-Cl ₂ -C ₆ H ₃ -CH ₂ H 146 ch ₃ 2,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH _{2 (} H ¹⁴⁷ ch ₃ 2,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ ' H 148 ch ₃ 3,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ H 149 ch ₃ 3,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ H 150 ch _{3 l-naphthyl-CH2} H 151 ch _{3 2-naphthyl-CH2} H 152 ch ₃ c ₆ h ₅ -ch (ch ₃ ) H 153 ch ₃ 2-Cl-C ₆ H ₄ -CH (CH ₃₎ H 154 ch ₃ 3-Cl-C ₆ H ₄ -CH (CH ₃₎ H 155 ch ₃ 4-Cl-C ₆ H ₄ -CH (CH ₃₎ T '. H 156 ch ₃ 2-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) H 157 ch ₃ 3-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) H 158 ch ₃ 4-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) H 159 ch ₃ 2-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) H 160 ch ₃ 3-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) H 161 ch ₃ 4-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) H 162 ch ₃ 2-tert-C ₄ H ₉ -C ₆ H ₄ -CH (CH ₃ ) H 163 ch ₃ 3-tert-C ₄ H _g -C ₆ H ₄ -CH (CH ₃ ) H 164 ch ₃ 4-tert-C ₄ H _g -C ₆ H ₄ -CH (CH ₃ ) H 165 ch ₃ 2-CH ₃ OC ₆ H ₄ -CH (CH ₃ ) H 166 ch ₃ 3-CH ₃ OC ₆ H ₄ -CH (CH ₃ ) H 167 ch ₃ 4-CH ₃ OC ₆ H ₄ -CH (CH ₃ ) H 168 ch ₃ 2-cyano-C ₆ H ₄ -CH (CH ₃₎ H 169 ch ₃ 3-cyano-C ₆ H ₄ -CH (CH ₃₎ H 170 ch ₃ 4-cyano-C ₆ H ₄ -CH (CH ₃₎ H 171 ch ₃ . 2,4-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) H 172 ch ₃ 3,4-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) H 173 ch ₃ 3,5-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) H 174 ch ₃ 2 ', 4- (CH ₃ ) ₂ -C ₆ H ₃ -CH (CH ₃ ) H

Table 4 - continued

Bile.

number R ¹ R ² R ⁴ 175 ch ₃ 2,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH (CH ₃ ) H 176 1 ch ₃ ch ₃ ooc-ch ₂ H | '177 ch ₃ c ₂ h ₅ ooc-ch ₂ H 178 ch ₃ ISO-C ₃ H ₇ OOC-CH ₂ H 179 ch ₃ tert-C ₄ H ₉ OOC-CH ₂ H 180 ch ₃ tert-C ₄ H ₉ OOC-CH (CH ₃ ) i H 181 ch ₃ n = c-ch ₂ H 182 ch ₃ ^C 6 ^H 5 ^C ° ^-CH 2 H 183 ch ₃ pyridin-2-ylmethyl H 184 ch ₃ pyrazin-2-ylmethyl H 185 ch ₃ pyrimidin-2-ylmethyl H ’·. 186 ^CH 3 ur-2-ylmethyl H 187 ch ₃ pyrrol-2-ylmethyl H 188 ch ₃ N-methylpyrrole-2-ylmethyl H 189 ch ₃ thien-2-ylmethyl H 190 ch ₃ oxazol-5-ylmethyl H 191 ch ₃ thiazol-2-ylmethyl H 192 ch ₃ thiazol-5-ylmethyl H 193 ch ₃ oxazol-2-ylmethyl H 194 ch ₃ pyrazol-3-ylmethyl H 195 ch ₃ benzofuran-2-ylmethyl H 196 ch ₃ indol-2-ylmethyl H 197 ch ₃ indol-3-ylmethyl H 198 ch ₃ benzothiazol-2-ylmethyl H 199 ^CH 3 quinolin-2-ylmethyl H 200 ch ₃ 4-ci-c ₆ h ₄ and (ch ₃ ) -ch ₂ H 201 H H ^C 2 ^H 5 202 H ch ₃ ^C 2 ^H 5 203 H t-C ₄ H ₉ ^C 2 ^H 5 204 H ch ₂ = ch-ch ₂ ^C 2 ^H 5

Table 4 - continued

Bile.

number R ¹ R ² R ⁴ 205 H CH ₂ = C (C1) -CH ₂ 5 ', 2' 206 H ch ₂ = c (ch ₃ ) -ch ₂ s ^C 2 ^H 5 207 H ch ₃ ch = ch-ch ₂ ^C 2 ^H 5 208 H HCsCCH ₂ ^C 2 ^H 5 209. H CH ₃ CsC-CH ₂ ^C 2 ^H 5 210 H cycloalkyl CGH ^ ^C 2 ^H 5 211 H ^C 6 ^H 5 ^CH 2 ^C 2 ^ 5 212 H 2-FC ₆ H ₄ -CH ₂ ^C 2 ^H 5 213 H 3-FC ₆ H ₄ -CH ₂ ^C 2 ^H 5 214 H 4-FC ₆ H ₄ -CH ₂ ^C 2 ^H 5 215 H 2-Cl-C ₆ H ₄ CH ₂ P ₂ ^H 5 216 H 3-Cl-C ₆ H ₄ CH ₂ ^C 2 ^H ₅ 217 H 4-Cl-C ₆ H ₄ CH ₂ ^C 2 ^H 5 218 H 2-Br-C ₆ H ₄ CH ₂ ^C 2 ^H 5 219 H 3-Br-C 8 H ₄ -CH ₂ ^C 2 ^H 5 220 H 4-Br-C ₆ H ₄ CH ₂ ^C 2 ^H 5 221 H 2-CH ₃ - ^C 6 ^H 4 -C 2 ^{H C} 2 ^H 5 222 H 3-CH ₃ -C ₆ H ₄ -CH ₂ ^C 2 ^H 5 223 H 4-CH ₃ -C ₆ ^h 4 ^-c H 2 ^C 2 ^H 5 224 H 2-CF ₃ -C ₆ H ₄ -CH ₂ ^C 2 ^H 5 225 H 3-CF ₃ -C ₆ H ₄ -CH ₂ ^C 2 ^H 5 226 H 4-CF ₃ -C ₆ H ₄ -CH ₂ ^C 2 ^H 5 227 H 2-Azo-C ₃ H ₇ -C ₆ H ₄ -CH ₂ ^C 2 ^H 5 228 H 3 ~~ 155 p “Όβ H y“ CH2 ^C 2 ^H 5 229 H 4-iso-C ₃ H ₇ -C ₈ H ₄ -CH ₂ ^C 2 ^H 5 230 H 2-t-C ₄ H _g C ₆ H ₄ CH ₂ ^C 2 ^H 5 231 H 3-t-C ₄ H _{g 4 -CH2} -CgH ^C 2 ^H 5 232 H 4-tert-C ₄ H ₉ -C ₆ H ₄ -CH ₂ ^C 2 ^H 5 233 H 2-CH ₃ OC ₆ H ₄ -CH ₂ ^C 2 ^H 5 234 H 3-CH ₃ OC ₆ H ₄ -CH ₂ ^C 2 ^H 5

Table 4 - continued

Bile.

number r! R ²

235 H 4-CH ₃ OC ₆ H ₄ -CH ₂ ^C 2 ^H 5 236 H 2-cyano-C ₆ H ₄ CH ₂ ^C 2 ^H 5 237 H 3-cyano-C ₆ H ₄ CH ₂ ^C 2 ^H 5 238 H _{4-cyano-4-CH 2} CGH ^C 2 ^H 5 239 H _{2-nitro-4-CGH CH2} ^C 2 ^H 5 240 H _{3-nitro-4-CH 2} CGH ^C 2 ^H 5 241 H _{4-nitro-4-CGH CH2} ^C 2 ^H 5 242 H 2,4-Cl ₂ -C ₈ H ₃ -CH ₂ ^C 2 ^H 5 243 H 3,4-Cl ₂ -C 8 ^H ₃ ^-CH 2 ^C 2 ^H 5 244 H 3,5-Cl ₂ -C ₈ H ₃ -CH ₂ ^C 2 ^H 5 245 H 2,6-Cl ₂ -C ₈ H ₃ -CH ₂ ^C 2 ^H 5 246 H _2, 4 (C ^H 3) 2 ^C 6 ^H 3 ^CH 2 ^C 2 ^H 5 247 H 2,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ ^C 2 ^H 5 248 H 3,4- (CH ₃ ) ₂ -C ₈ H ₃ -CH ₂ ^C 2 ^H 5 249 H 3,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ ^C 2 ^H 5 250 H _{l-naphthyl-CH2} ^C 2 ^H 5 251 H _{2-naphthyl-CH2} ^C 2 ^H 5 252 H CGH ₅ CH (CH ₃₎ ^C 2 ^H 5 253 H 2-Cl-CGH ₄ -CH (CH ₃₎ ^C 2 ^H 5 254 H 3-Cl-CGH ₄ -CH (CH ₃₎ ^C 2 ^H 5 255 H 4-Cl-CGH ₄ -CH (CH ₃₎ ^C 2 ^H 5 256 H 2-CH ₃ -C ₈ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 257 H 3-CH ₃ -C ₈ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 258 H 4-CH ₃ -C ₈ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 259 H 2-CF ₃ -C ₈ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 260 H 3-CF ₃ -C ₈ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 261 H 4-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 262 H 2-tert-C ₄ H ₉ -C ₈ H ₄ -CH (CH ₃ ) ^G 2 ^ 5 263 H 3-tert-C ₄ H ₉ -C ₈ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 264 H 4-tert-C ₄ H ₉ -C ₈ H ₄ -CH (CH ₃ ) ^C 2 ^H 5

Table 4 - continued

Bile.

number R ¹

R ⁴

265 H 2-CH ₃ OC ₆ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 266 H 3-CH ₃ OC ₆ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 267 H 4-CH ₃ OC ₆ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 268 H 2-cyano-C ₆ H ₄ -CH (CH ₃₎ ^C 2 ^H 5 269 H 3-cyano-C ₆ H ₄ -CH (CH ₃₎ ^C 2 ^H 5 270 H 4-cyano-C ₆ H ₄ -CH (CH ₃₎ ^C 2 ^H 5 271 H 2,4-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) ^C 2 ^H 5 272 H 3,4-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) ^C 2 ^H 5 273 H 3,5-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) ^C 2 ^H 5 274 H 2,4- (CH ₃ ) ₂ -C ₈ H ₃ -CH (CH ₃ ) ^C 2 ^H 5 275 H 2,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH (CH ₃ ) ^C 2 ^H 5 276 H ch ₃ ooc-ch ₂ ^C 2 ^H 5 277 H c ₂ h ₅ ooc-ch ₂ ^C 2 ^H 5 278 H CI-C ₃ H ₇ OOC-CH ₂ ^C 2 ^H 5 279 H tert-C ₄ H ₉ OOC-CH ₂ ^C 2 ^H 5 280 H tert-C ₄ H ₉ OOC-CH (CH ₃ ) ^C 2 ^H 5 281 H n = c-ch ₂ ^C 2 ^H 5 282 H ^C 6 ^H 5 ^C ° ^-CH 2 ^C 2 ^H 5 283 H pyridin-2-ylmethyl ^C 2 ^H 5 284 H pyrazin-2-ylmethyl ^C 2 ^H 5 285 H pyrimidin-2-ylmethyl ^C 2 ^H 5 286 H fur-2-ylmethyl ^C 2 ^H 5 287 H pyrrol-2-ylmethyl ^C 2 ^H 5 288 H N-methylpyrrole-2-ylmethyl ^C 2 ^H 5 289 H thien-2-ylmethyl ^C 2 ^H 5 290 H isoxazol-5-ylmethyl ^C 2 ^H 5 291 H thiazol-2-ylmethyl ^C 2 ^H 5 292 H thiazol-5-ylmethyl ^C 2 ^H 5 293 H oxazol-2-ylmethyl ^C 2 ^H 5 294 H pyrazol-3-ylmethyl ^C 2 ^H 5

Table 4 - continued

Bile.

number R ¹ R ² R ⁴ 295 H benzofuran-2-ylmethyl ^C 2 ^H 5 296 H indol-2-ylmethyl ^C 2 ^H 5 297 H indol-3-ylmethyl ^C 2 ^H 5 298 H benzothiazol-2-ylmethyl ^C 2 ^H 5 299 H quinolin-2-ylmethyl ^C 2 ^H 5 300 H 4-ci-c ₆ h ₄ and (ch ₃ ) -ch ₂ ^C 2 ^H 5 301 ch ₃ H ^C 2 ^H 5 302 ch ₃ ch ₃ ^C 2 ^H 5 303 ch ₃ t-C ₄ H _g ^C 2 ^H 5 304 ch ₃ ch ₂ = ch-ch ₂ ^C 2 ^H 5 305 ch ₃ ch ₂ = c (ci) -ch ₂ ^C 2 ^H 5 306 , ^CH 3 ch ₂ = c (ch ₃ ) -ch ₂ ^C 2 ^H 5 307 ch ₃ ch ₃ ch = ch-ch ₂ ^C 2 ^H 5 308 ch ₃ HC = CH ₂ ^C 2 ^H 5 309 ch ₃ ch ₃ c = c-ch ₂ ^C 2 ^H 5 310 ch ₃ cycloalkyl CgHjj ^C 2 ^H 5 311 ch ₃ ^C 6 ^H 5 ^CH 2 ^C 2 ^H 5 312 ch ₃ 2-FC ₆ H ₄ -CH ₂ ^C 2 ^H 5 313 ch ₃ 3-FC ₆ H ₄ -CH ₂ ^C 2 ^H 5 314 ch ₃ 4-FC ₆ H ₄ -CH ₂ ^C 2 ^H 5 315 ch ₃ 2-Cl-C ₆ H ₄ CH ₂ ^C 2 ^H 5 316 ch ₃ 3-Cl-C ₆ H ₄ CH ₂ ^C 2 ^H 5 317 ch ₃ 4-Cl-C ₆ H ₄ CH ₂ ^C 2 ^H 5 318 ch ₃ 2-Br-C ₆ H ₄ CH ₂ ^C 2 ^H 5 319 ch ₃ 3-Br-C ₆ H ₄ CH ₂ ^C 2 ^H 5 320 ch ₃ 4-Br-C ₆ H ₄ CH ₂ ^C 2 ^H 5 321 ch ₃ 2-CH ₃ -C ₆ H ₄ -CH ₂ ^C 2 ^H 5 322 ch ₃ 3-CH ₃ -C ₆ H ₄ -CH ₂ ^C 2 ^H 5 323 ch ₃ 4-CH ₃ ^-C 6 ^H 4 ^-ch 2 ^C 2 ^H 5 324 ch ₃ 2-CF ₃ -C ₆ H ₄ -CH ₂ ^C 2 ^H 5

Table 4 - continued

Bile.

number R ¹ R ² R ⁴ 325 ch ₃ 3-CF ₃ -C ₆ H ₄ -CH ₂ ^C 2 ^H 5 326 ch ₃ 4-CF ₃ -C ₆ H ₄ - ^c H ₂ ^c 2 ^H 5 327 ch ₃ 2-C20-C ₃ H ₇ -C ₆ H ₄ -CH ₂ ^ 2¾ 328 ch ₃ 3-ISO-C ₃ H ₇ -C ₈ H ₄ -CH ₂ ^C 2 ^H 5 329 ch ₃ 4-ixo-C ₃ H ₇ -C ₆ H ₄ -CH ₂ ^C 2 ^H 5 330 ch ₃ 2-tert-C ₄ H ₉ -C ₆ H ₄ -CH ₂ ^C 2 ^H 5 331 ch ₃ 3-tert-C ₄ H ₉ -C ₆ H ₄ -CH ₂ ^C 2 ^H 5 332 ch ₃ 4-tert-C ₄ H ₉ -C ₈ H ₄ -CH ₂ ^C 2 ^ 5 333 ch ₃ 2-CH ₃ OC ₆ H ₄ -CH ₂ ^C 2 ^H 5 334 ch ₃ 3-CH ₃ OC ₆ H ₄ -CH ₂ ^C 2 ^H 5 335 ch ₃ 4-CH ₃ O-C ₆ H ₄ -CH ₂ ^ 2¾ 336 ch _{3 2-cyano-4-CH 2} CGH ^C 2 ^H 5 337 ch _{3 3-cyano-4-CH 2} CGH ^C 2 ^H 5 338 ch ₃ 4-cyano-C ₆ H ₄ CH ₂ ^C 2 ^H 5 339 ch _{3 2-nitro-4-CH 2} CGH ^C 2 ^H 5 340 ch ₃ 3-nitro-C ₆ H ₄ CH ₂ ^C 2 ^H 5 341 ch ₃ 4-nitro-C ₆ H ₄ CH ₂ ^C 2 ^H 5 342 ch ₃ 2,4-Cl ₂ -C ₆ H ₃ -CH ₂ ^C 2 ^H 5 343 ch ₃ 3,4-Cl ₂ -C ₆ ^h ₃ -CB ₂ ^C 2 ^H 5 344 ch ₃ 3,5-Cl ₂ -C ₆ ^H 3 ^-CH 2 ^C 2 ^H 5 345 ch ₃ 2,6-Cl ₂ -C ₆ H ₃ -CH ₂ 346 ch ₃ 2,4- (CH ₃ ) ₂ -C ₈ H ₃ -CH ₂ ^C 2 ^H 5 347 ch ₃ 2,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ ^C 2 ^H 5 348 ch ₃ 3,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ ^C 2 ^H 5 349 ch ₃ 3,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ ^C 2 ^H 5 350 ch _{3 l-naphthyl-CH2} ^C 2 ^H 5 351 ch _{3 2-naphthyl-CH2} ^C 2 ^H 5 352 ch ₃ c ₆ h ₅ -ch (ch ₃ ) ^C 2 ^H 5 353 ch ₃ 2-Cl-CGH ₄ -CH (CH ₃₎ ^C 2 ^H 5 354 ch ₃ 3-Cl-C ₆ H ₄ -CH (CH ₃₎ ^C 2 ^H 5

Table 4 - continued

Bile.

number R ¹ R ²

355 ch ₃ 4-Cl-C ₆ H ₄ -CH (CH ₃ ) ^c 2 ^h 5 356 ch ₃ 2-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) ^c 2 ^h 5 357 ch ₃ 3-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 358 ch ₃ 4-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 359 ch ₃ 2-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 360 ch ₃ 3-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 361 ch ₃ 4-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 362 ch ₃ 2-tert-C ₄ H ₉ -C ₆ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 363 ch ₃ 3-tert-C ₄ H _g -C ₆ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 364 ch ₃ 4-tert-C ₄ H ₉ -C ₆ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 365 ch ₃ 2-CH ₃ OC ₆ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 366 ch ₃ 3-CH ₃ O-C ₈ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 367 ch ₃ 4-CH ₃ OC ₆ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 368 ch ₃ 2-cyano-C ₆ H ₄ -CH (CH ₃₎ ^C 2 ^H 5 369 ch ₃ 3-cyano-C ₆ H ₄ -CH (CH ₃₎ ^C 2 ^H 5 370 ch ₃ 4-cyano-C ₆ H ₄ -CH (CH ₃₎ ^C 2 ^H 5 371 ch ₃ 2,4-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) ^C 2 ^H 5 372 ch ₃ 3,4-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) ^C 2 ^H 5 373 ch ₃ 3,5-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) \ ^C 2 ^H 5 374 ch ₃ 2,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH (CH ₃ ) ^C 2 ^H 5 375 ch ₃ 2,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH (CH ₃ ) ^C 2 ^H 5 376 ch ₃ ch ₃ ooc-ch ₂ ^C 2 ^H 5 377 ch ₃ c ₂ h ₅ ooc-ch ₂ ^C 2 ^H 5 378 ch ₃ 2Zo-C ₃ H ₇ OOC-CH ₂ ^C 2 ^H 5 379 ch ₃ tert-C ₄ H ₉ OOC-CH ₂ 5 ', 2' 380 ch ₃ tert-C ₄ H ₉ OOC-CH (CH ₃ ) ^C 2 ^H 5 381 ch _{3 NSC-CH2} ^C 2 ^H 5 382 ch ₃ c ₆ h ₅ co-ch ₂ ^C 2 ^H 5 383 ch ₃ pyridin-2-ylmethyl ^C 2 ^H 5 384 ch ₃ pyrazin-2-ylmethyl ^C 2 ^H 5

Table 4 - continued

Bile.

number R ¹

385 ch ₃ pyrimidin-2-ylmethyl ^C 2 ^H 5 386 ch ₃ fur-2-ylmethyl ^C 2 ^H 5 387 ch ₃ pyrrol-2-ylmethyl ^C 2 ^H 5 388 ch ₃ N-methylpyrrole-2-ylmethyl ^C 2 ^H 5 389 ch ₃ thien-2-ylmethyl ^C 2 ^ 5 390 ch ₃ isoxazol-S-ylmethyl ^C 2 ^H 5 391 ch ₃ thiazol-2-ylmethyl ^C 2 ^H 5 392 ch ₃ thiazol-5-ylmethyl ^C 2 ^H 5 393 ch ₃ oxazol-2-ylmethyl ^C 2 ^H 5 394 ch ₃ pyrazol-3-ylmethyl ^C 2 ^H 5 395 ch ₃ benzofuran-2-ylmethyl ^C 2 ^H 5 396 ch ₃ indol-2-ylmethyl ^C 2 ^H 5 397 ch ₃ indol-3-ylmethyl ^C 2 ^H 5 398 ^CH 3 benzothiazol-2-ylmethyl ^C 2 ^H 5 399 ch ₃ quinolin-2-ylmethyl ^C 2 ^H 5 400 ch ₃ 4-ci-c ₆ h ₄ and (ch ₃ ) -ch ₂ ^C 2 ^H 5

Table 5

R ¹ ° Y ^A 'N- ⁰ ''Ofe ₎

N ch / 'ch ₃

Bile.

number r! R ²

1 H H 2 H ch ₃ 3 H t-C ₄ H _g 4 H ch ₂ = ch-ch ₂ 5 H CH ₂ = C (C1) -CH ₂ 6 H CH ₂ = C (CH ₃ ) -CH ₂ 7 H ch ₃ ch = ch-ch ₂ 8 H hc = cch ₂ 9 H ch ₃ c = c-ch ₂ 10 H cycloalkyl CGH !! 11 H c ₆ h ₅ -ch ₂ 12 H 2-FC ₆ H ₄ -CH ₂ 13 H 3-FC ₆ H ₄ -CH ₂ 14 H 4-FC ₆ H ₄ -CH ₂ 15 H 2-Cl-C ₆ H ₄ CH ₂ 16 H 3-Cl-C ₆ H ₄ CH ₂ 17 H 4-Cl-C ₆ H ₄ CH ₂ 18 H 2-Br-C ₆ H ₄ CH ₂ 19 H 3-Br-C ₆ H ₄ CH ₂ 20 H 4-Br-C ₆ H ₄ CH ₂ 21 H 2-CH ₃ -C ₆ H ₄ -CH ₂ 22 H 3-CH ₃ -C ₆ H ₄ -CH ₂ 23 H 4-CH ₃ -C ₆ H ₄ -CH ₂

Table 5 - continued

Bile.

number R ¹ R ²

24 H 2-CF ₃ -C ₆ H ₄ -CH ₂ 25 H 3-CF ₃ -C ₆ H ₄ -CH ₂ 26 H 4-CF ₃ -C ₆ H ₄ -CH ₂ 27 H 21Zo-C ₃ H ₇ -C ₈ H ₄ -CH ₂ 28 H 3,120 C ₃ H ₇ -C ₈ H ₄ -CH ₂ 29 H 4-ZO-C ₃ H ₇ -C ₈ H ₄ -CH ₂ 30 H 2-tert-C ₄ H ₉ -C ₆ H ₄ -CH 31 H 3-tert-C ₄ H ₉ -C ₆ H ₄ -CH 32 H 4-tert-C ₄ H ₉ -C ₆ H ₄ -CH 33 H 2-CH ₃ OC ₆ H ₄ -CH ₂ 34 H 3-CH ₃ OC ₆ H ₄ -CH ₂ 35 H 4-CH ₃ OC ₆ H ₄ -CH ₂ 36 H 2-cyano-C ₆ H ₄ -CH ₂ 37 H 3-cyano-C ₆ H ₄ -CH ₂ 38 H 4-cyano-C ₆ H ₄ CH ₂ 39 H 2-nitro-C ₆ H ₄ CH ₂ 40 H 3-nitro-C ₆ H ₄ CH ₂ 41 H 4-nitro-C ₆ H ₄ -CH ₂ 42 H 2,4-Cl ₂ -C ₆ H ₃ -CH ₂ 43 H 3,4-Cl ₂ -C ₆ H ₃ -CH ₂ 44 H 3,5-Cl ₂ -C ₆ H ₃ -CH ₂ 45 H 2,6-Cl ₂ -C ₆ ^h ₃ ^-CH 2 46 H 2,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ 47 H 2,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ 48 H 3,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ 49 H 3,5- (CH ₃ ) ₂ ^-C 6 ^H 3 ^-c H 2 50 H _{1-naphthyl-CH2} 51 H _{2-naphthyl-CH2} 52 H c ₆ h ₅ -ch (ch ₃ ) 53 H 2-Cl-C ₆ H ₄ -CH (CH ₃₎

Table 5 - continued

Bile.

number R ¹ R ²

54 H 3-Cl-C ₆ H ₄ -CH (CH ₃₎ 55 H 4-Cl-C ₆ H ₄ -CH (CH ₃ ) 56 H 2-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) 57 H 3-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) 58 H 4-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) 59 H 2-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) 60 H 3-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) 61 H 4-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) 62 H 2-tert-C ₄ H ₉ -C ₆ H ₄ -CH (CH ₃ ) 63 H 3-tert-C ₄ H ₉ -C ₆ H ₄ -CH (CH ₃ ) 64 H 4-tert-C ₄ H ₉ -C ₆ H ₄ -CH (CH ₃ ) 65 H 2-CH ₃ OC ₆ H ₄ -CH (CH ₃ ) 66 H 3-CH ₃ OC ₆ H ₄ -CH (CH ₃ ) 67 H 4-CH ₃ OC ₆ H ₄ -CH (CH ₃ ) 68 H 2-cyano-C ₆ H ₄ -CH (CH ₃₎ 69 H 3-cyano-C ₆ H ₄ -CH (CH ₃₎ 70 H 4-cyano-C ₆ H ₄ -CH (CH ₃₎ 71 H 2,4-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) 72 H 3,4-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) 73 H 3,5-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) 74 H 2,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH (CH ₃ ) 75 H 2,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH (CH ₃ ) 76 H ch ₃ ooc-ch ₂ 77 H C ₂ H ₅ OOC-CH ₂ 78 H ISO-C ₃ H ₇ OOC-CH ₂ 79 H tert-C ₄ H ₉ OOC-CH ₂ 80 H tert-C ₄ H _g OOC-CH (CH ₃ ) 81 H n = c-ch ₂ 82 H ^c 6 ^H 5 ^C ° ^-CH 2 83 H pyridin-2-ylmethyl

Table 5 - continued

Bile.

the numbers you hear R ¹ R ² 84 H pyrazin-2-ylmethyl 85 H pyrimidin-2-ylmethyl 86 H fur-2-ylmethyl 87 H pyrrol-2-ylmethyl 88 H N-methylpyrrole-2-ylmethyl 89 H thien-2-ylmethyl 90 H isoxazol-5-ylmethyl 91 H thiazol-2-ylmethyl 92 H thiazol-5-ylmethyl 93 H oxazol-2-ylmethyl 94 H pyrazol-3-ylmethyl 95 H benzofuran-2-ylmethyl 96 H indol-2-ylmethyl 97 H indol-3-ylmethyl 98 H benzothiazol-2-ylmethyl 99 H quinolin-2-ylmethyl 100 H 4-ci-c ₆ h ₄ and (ch ₃ ) -ch ₂ 101 ch ₃ H 102 ch ₃ ch ₃ 103 ch ₃ t-C ₄ H ₉ 104 ch ₃ ch ₂ = ch-ch ₂ 105 ch ₃ CH ₂ = C (C1) -CH ₂ 106 ch ₃ CH ₂ = C (CH ₃ ) ₂ CH ₂ 107 ch ₃ ch ₃ ch = ch-ch ₂ 108 ch ₃ hc = cch ₂ 109 ch ₃ CH ₃ CsC-CH ₂ 110 ch ₃ Cyclo-cghj! 111 ch ₃ ^C 6 ^H 5 " ^CH 2 112 ch ₃ 2-FC ₆ H ₄ -CH ₂ 113 ch ₃ 3-FC ₆ H ₄ -CH ₂

Table 5 - continued

Bile.

number R ¹ R ²

114 ch ₃ 4-FC ₆ H ₄ -CH ₂ 115 ch ₃ 2-Cl-C ₆ H ₄ CH ₂ 116 ch ₃ 3-Cl-C ₆ H ₄ CH ₂ 117 ch ₃ 4-Cl-C ₆ H ₄ CH ₂ 118 ch ₃ 2-Br-C 8 H ₄ -CH ₂ 119 ch ₃ 3-Br-C ₆ H ₄ CH ₂ 120 ch ₃ 4-Br-C 8 H ₄ -CH ₂ 121 ch ₃ 2-CH ₃ -C ₆ H ₄ -CH ₂ 122 ch ₃ 3-CH ₃ -C ₈ H ₄ -CH ₂ 123 ch ₃ 4-CH ₃ -C ₈ H ₄ -CH ₂ 124 ch ₃ 2-CF ₃ -C ₈ H ₄ -CH ₂ 125 ch ₃ 3-CF ₃ - ^c 6 ^H 4 ^-CH 2 126 ch ₃ 4-CF ₃ -C ₆ H ₄ -CH ₂ 127 ch ₃ 2-iso-C ₃ H ₇ -C ₈ H ₄ -CH ₂ 128 ch ₃ 3-ISO-C ₃ H ₇ -C ₈ H ₄ -CH 2 129 ch ₃ 4-ISO-C ₃ H ₇ -C ₈ H ₄ -CH ₂ 130 ch ₃ 2-tert-C ₄ H ₉ -C ₈ H ₄ -CH 131 ch ₃ 3-tert-C ₄ H ₈ -C ₈ H ₄ -CH 132 ch ₃ 4-t-C ₄ H _g -CgH _4-CH 133 ch ₃ 2-CH ₃ O-C ₈ H ₄ -CH ₂ 134 ch ₃ 3-CH ₃ O-C ₈ H ₄ -CH ₂ 135 ch ₃ 4-CH ₃ O-C ₈ H ₄ -CH ₂ 136 ch _{3 2-cyano-4-CH 2} CGH 137 ch _{3 3-cyano-4-CGH CH2} 138 ch _{3 4-cyano-4-CH 2} CGH 139 ch _{3 2-nitro-4-CGH} CH2 140 ch _{3 3-nitro-4-CH2} CGH 141 ch _{3 4-nitro-4-CH 2} CGH 142 ch ₃ 2,4-Cl ₂ ^-C 6 ^H ₃ ^-CH 2 143 ch ₃ 3,4-Cl ₂ -C ₆ H ₃ -CH ₂

Table 5 - continued

Bile.

number R ¹ R ²

144 ch ₃ 3,5-Cl ₂ -C ₆ H ₃ -CH ₂ 145 ch ₃ 2,6-Cl ₂ -C ₆ H ₃ -CH ₂ 146 ch ₃ 2,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ 147 ch ₃ 2,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ 148 ch ₃ 3,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ 149 ch ₃ 3,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ 150 ch _{3 l-naphthyl-CH2} 151 ch _{3 2-naphthyl-CH2} 152 ^CH 3 ^C 6 ^H 5 ^-CH ( ^CH 3) 153 ch ₃ 2-Cl-C ₆ H ₄ -CH (CH ₃₎ 154 ch ₃ 3-Cl-C ₆ H ₄ -CH (CH ₃₎ 155 ch ₃ 4-C1-C ₆ H ₄ -CH (CH ₃₎ 156 ch ₃ 2-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) 157 ch ₃ 3-CH ₃ -C ₆ H ₄ -CH (CW ₃ ) 158 ch ₃ 4-CH ₃ -C ₆ H ₄ -CH (CM ₃ ) 159 ch ₃ 2-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) 160 ch ₃ 3-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) 161 ch ₃ 4-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) 162 ch ₃ 2-tert-C ₄ H ₉ -C ₆ H ₄ -CH (CH ₃ ) 163 ch ₃ 3-tert-C ₄ H ₉ -C ₆ H ₄ -CH (CH ₃ ) 164 ch ₃ 4-tert-C ₄ H ₉ -C ₆ H ₄ -CH (CH ₃ ) 165 ch ₃ 2-CH ₃ OC ₆ H ₄ -CH (CH ₃ ) 166 ch ₃ 3-CH ₃ OC ₆ H ₄ -CH (CH ₃ ) 167 ch ₃ 4-CH ₃ OC ₆ H ₄ -CH (CH ₃ ) 168 ch ₃ 2-cyano-C ₆ H ₄ -CH (CH ₃₎ 169 ch ₃ 3-cyano-C ₆ H ₄ -CH (CH ₃₎ 170 ch ₃ 4-cyano-C ₆ H ₄ -CH (CH ₃₎ 171 ch ₃ 2,4-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) 172 ch ₃ 3,4-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) 173 ch ₃ 3,5-Cl ₂ -C ₆ H ₃ -CH (CH ₃ )

Table 5 - continued

Bile.

number R ¹ R ²

174 ch ₃ 2,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH (CH ₃ ) 175 ch ₃ 2,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH (CH ₃ ) 176 ch ₃ CH ₃ OOC-CH ₂ 177 ch ₃ c ₂ h ₅ ooc-ch ₂ 178 ch ₃ IR-C ₃ H ₇ OC-CH ₂ 179 ch ₃ tert-C ₄ H ₉ OOC-CH ₂ 180 ch ₃ t. -C ₄ H ₉ OOC-CIi (CH ₃ ) 181 ch _{3 N-C-CH2} 182 ch ₃ ^C 6 ^H 5 ^C ° ^-CH 2 183 ch ₃ pyridin-2-ylmethyl 184 ch ₃ pyrrolidine-2-ylmethyl 185 ch ₃ pyrimidin-2-ylmethyl 186 ch ₃ fur-2-ylmethyl 187 ch ₃ pyrrol-2-ylmethyl 188 ch ₃ N-methylpyrrole-2-ylmethyl 189 ch ₃ thien-2-ylmethyl 190 ch ₃ isoxazol-5-ylmethyl 191 ch ₃ thiazol-2-ylmethyl 192 ch ₃ thiazol-5-ylmethyl 193 ch ₃ oxazol-2-ylmethyl 194 ch ₃ pyrazol-3-ylmethyl 195 ch ₃ benzofuran-2-ylmethyl 196 ch ₃ indol-2-ylmethyl 197 ch ₃ indol-3-ylmethyl 198 ch ₃ benzothiazol-2-ylmethyl 199 ch ₃ quinolin-2-ylmethyl 200 ch ₃ 4-ci-c ₆ h ₄ and (ch ₃ ) -ch ₂

Table 6

R ² \

R ⁶

from*

OCH ₃

-NHR ⁴ ° C.

Bile.

number R ¹ R ² R ⁴ R ¹ 1 H H H H 2 H ch ₃ H H 3 H t-C ^ Hg H H 4 H ch ₂ = ch-ch ₂ H H 5 H ch ₂ = c (c 1) -ch ₂ H H 6 H ch ₂ = c (ch ₃ ) -ch ₂ H H 7 H ch ₃ ch = ch-ch ₂ H H 8 H HCsCCH ₂ H H 9 H ch ₃ c = c-ch ₂ H H 10 H CGH-cycloalkyl-Q H H 11 H ^C 6 ^H 5 ^CH 2 H H 12 H 2-FC ₆ H ₄ -CH ₂ H H 13 H 3-FC ₆ H ₄ -CH ₂ H H 14 H 4-FC ₆ H ₄ -CH ₂ H H ¹⁵ H 2-Cl-C ₆ H ₄ CH ₂ H H 16 H 3-Cl-C ₆ H ₄ CH ₂ H H 17 H 4-Cl-C ₆ H ₄ CH ₂ H H 18 H 2-Br-C ₆ H ₄ CH ₂ H H 19 H 3-Br-C ₆ H ₄ CH ₂ H H 20 H 4-Br-C ₆ H ₄ CH ₂ H H 21 H 2-CH ₃ -C ₆ H ₄ -CH ₂ H H 22 H 3-CH ₃ -C ₆ H ₄ -CH ₂ H H 23 H 4-CH ₃ - ^c ₆ H ₄ - ^CH 2 H H 24 H 2-CF ₃ -C ₆ H ₄ -CH ₂ H H

Table 6 - continued

Bile.

number R ¹ R ² R ⁴ R ⁶ 25 H 3-CF ₃ - ^c 6 ^h 4 ^-CH 2 H H 26 H 4-CF ₃ -C ₆ H ₄ -CH ₂ H H 27 H 2-C20-C ₃ H ₇ -C ₆ H ₄ -CH ₂ H H 28 H 3-iso-C ₃ H ₇ -C ₆ H ₄ -CH ₂ H H 29 H 4-iso-C ₃ H ₇ -C ₆ H ₄ -CH ₂ H H 30 H 2-tert-C ₄ H ₉ -C ₆ H ₄ -CH ₂ H H 31 H 3-tert-C ₄ H ₉ -C ₆ H ₄ -CH ₂ H H 32 H 4-tert-C ₄ H ₉ -C ₈ H ₄ -CH ₂ H H 33 H 2-CH ₃ OC ₆ H ₄ -CH ₂ H H 34 H 3-CH ₃ OC ₆ H ₄ -CH ₂ H H 35 H 4-CH ₃ OC ₆ H ₄ -CH ₂ H H 36 H 2-cyano-C ₆ H ₄ -CH ₂ H H 37 H 3-cyano-C ₆ H ₄ -CH ₂ H H 38 H 4-cyano-C ₆ H ₄ CH ₂ H H 39 H _{2-nitro-4-CH 2} CGH H H 40 H 3-nitro-C ₆ H ₄ CH ₂ H H 41 H 4-nitro-C ₆ H ₄ -CH ₂ H H 42 H ^2, 4-Cl2- ^C 6 ^H ₃ C ^H 2 H H 43 H 3,4-Cl ₂ -C ₆ H ₃ -CH ₂ H H 44 H 3,5-Cl ₂ -C ₆ H ₃ -CH ₂ H H : 45 H 2,6-Cl ₂ -C ₆ H ₃ -CH ₂ H H ‘46 H 2,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ H H 47 H 2,5- (CH ₃ ) ₂ -C ₈ H ₃ -CH ₂ H H 48 H 3,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ H H 49 H 3,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ H H 50 H _{l-naphthyl-CH2} H H 51 H _{2-naphthyl-CH2} H H 52 H C ₆ H ₅ -CH (CH ₃ ) H H 53 H 2-Cl-C ₆ H ₄ -CH (CH ₃₎ H H 54 H 3-Cl-C ₆ H ₄ -CH (CH ₃₎ H H

Table 6 - continued

Bile.

number R ¹ R ² R ⁴ R ⁶ 55 H 4-Cl-C ₆ H ₄ -CH (CH ₃ ) H H 56 H 2-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) H H 57 H 3-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) H H 58 H 4-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) H H 59 H 2-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) H H 60 H; • i 3-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) H H 61 H ¹ 4-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) H H 62 H 2-tert-C ₄ H ₉ -C ₆ H ₄ -CH (CH ₃ ) H H 63 H 3-tert-C ₄ H _g -C ₆ H ₄ -CH (CH ₃ ) H H 64 H 4-tert-C ₄ H ₉ -C ₆ H ₄ -CH (CH ₃ ) H H 65 H 2-CH ₃ OC ₆ H ₄ -CH (CH ₃ ) H H 66 H 3-CH ₃ OC ₆ H ₄ -CH (CH ₃ ) H H 67 H 4-CH ₃ OC ₆ H ₄ -CH (CH ₃ ) H H 68 H 2-cyano-C ₆ H ₄ -CH (CH ₃₎ H H 6 * 9 H 3-cyano-C ₆ H ₄ -CH (CH ₃₎ H H 70 H 4-cyano-C ₆ H ₄ -CH (CH ₃₎ H H 71 H 2,4-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) H H 72 H 3,4-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) H H 73 H 3,5-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) H H 74 H 2,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH (CH ₃ ) H H . 75 H 2,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH (CH ₃ ) H H * 76 H ch ₃ ooc-ch ₂ H H 77 H c ₂ h ₅ ooc-ch ₂ H H 78 H Ezo-C ₃ H ₇ OOC-CH ₂ H H 79 H tert-C ₄ H ₉ OOC-CH ₂ H H 80 H tert-C ₄ H ₉ OOC-CH (CH ₃ ) H H 81 H _NSC-CH2 H H 82 H c ₆ h ₅ co-ch ₂ H H 83 H pyridin-2-ylmethyl H H 84 H pyrazin-2-ylmethyl H H

100

Table 6 - continued

Bile.

number R ¹ R ²

R ⁴

85 H pyrimidin-2-ylmethyl H H 86 H fur-2-ylmethyl H H 87 H pyrrol-2-ylmethyl H H 88 H N-methylpyrrole-2-ylmethyl H H 89 H thien-2-ylmethyl H. H 90 H isoxazolr-5-ylmethyl H H 91 H thiazol-2-ylmethyl H H 92 H thiazol-5-ylmethyl H H 93 H oxazol-2-ylmethyl H H 94 H pyrazol-3-ylmethyl H H 95 H benzofuran-2-ylmethyl H H 96 H indol-2-ylmethyl H H 97 H indol-3-ylmethyl H H 98 H benzothiazol-2-ylmethyl H H 99 H quinolin-2-ylmethyl H H 100 H 4-ci-c ₆ h ₄ and (ch ₃ ) -ch ₂ H H 101 ch ₃ H H H 102 ch ₃ ch ₃ H H 103 ch ₃ t. ^- C ₄ H _g H H 104 ch ₃ ch ₂ = ch-ch ₂ H H 105 ch ₃ ch ₂ = c (c 1) -ch ₂ H H 106 ch ₃ CH ₂ = C (CH ₃ ) -CH ₂ H H 107 ch ₃ ch ₃ ch = ch-ch ₂ H H 108 ch ₃ HCsCCH ₂ H H 109 ch ₃ CH ₃ CsC-CH ₂ H H 110 ch ₃ cycloalkyl CgHjj H H 111 ch ₃ ^C 6 ^H 5 ^CH 2 H H 112 ch ₃ 2-F-C 8 H ₄ -CH ₂ H H 113 ch ₃ ³ -F- ^C 6 ^H 4 ^-CH 2 H H 114 ch ₃ 4-F-C 8 H ₄ -CH ₂ H H

101

Table 6 - continued

Bile.

number R ¹ R ² R ⁴ R ¹ 115 ch ₃ 2-Cl-C ₆ H ₄ CH ₂ H H 116 ^CH 3, 3-Cl-C ₆ H ₄ CH ₂ H H 117 .ch ₃ ' 4-Cl-C ₆ H ₄ CH ₂ H H 118 ch ₃ 2-Br-C ₆ H ₄ CH ₂ H H 119 ch ₃ 3-Br-C ₆ H ₄ -CH ₂ H H 120 ch ₃ 4 'Br-C ₆ H ₄ -CH ₂ H • H and 121 ch ₃ 2-CH ₃ -C ₆ H ₄ -CH ₂ H H 122 ch ₃ 3-CH ₃ -C ₆ H ₄ -CH ₂ H H 123 ch ₃ 4-CH ₃ -C ₆ ^h ₄ -CH ₂ H H 124 ch ₃ ² - ^CF 3 - ^C 6 ^H 4 - ^CH 2 H H 125 ch ₃ 3cd ₃ -c ₆ h ₄ -ch ₂ H H 126 ch ₃ 4-CF ₃ ^-C 6 ^H 4 ^-CH 2 H H 127 ch ₃ 2-iso-C ₃ H ₇ -C ₈ H ₄ -CH ₂ H H 128 ch ₃ 3-ICO-C ₃ H ₇ -C ₆ H ₄ -CH ₂ H H 129 ch ₃ 4-iso-C ₃ H _{7-C 6} H ₄ -CH ₂ H H 130 ch ₃ 2-tert-C ₄ H ₉ -C ₈ H ₄ -CH ₂ H H 131 ch ₃ 3-t-C ₄ H _g C ₆ H ₄ CH ₂ H H 132 ch ₃ 4-tert-C ₄ H ₈ -C ₆ H ₄ -CH ₂ H H 133 ch ₃ 2-CH ₃ O-C ₆ H ₄ -CH ₂ H H 134 ^CH 3 3-CH ₃ OC ₆ H ₄ -CH ₂ H H 135 ch ₃ 4-CH ₃ OC ₆ H ₄ -CH ₂ H H 136 ch ₃ 2-cyano-C ₆ H ₄ CH ₂ í H H 137 ch ₃ 3-cyano-C ₆ H ₄ CH ₂ H H 138 ch _{3 4-cyano-4-CH 2} CGH H H 139 ch _{3 2-nitro-4-CGH CH2} H . H 140 ch _{3 3-nitro-4-CH 2} CGH H H 141 ch _{3 4-nitro-4-CH 2} CGH H H 142 ch ₃ 2,4 'Cl ₂ -C ₈ H ₃ -CH ₂ H H 143 ^CH 3; 3,4-Cl ₂ -C ₆ H ₃ -CH ₂ H H 144 ch ₃ 3,5-Cl ₂ -C ₈ H ₃ -CH ₂ H H

102

Table 6 - continued

Bile.

number R ¹ R ² R ⁴ R ⁶ 145 ch ₃ 2,6-Cl ₂ -C ₆ H ₃ -CH ₂ H H 146 ch ₃ 2,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ H 1 ^H 147 ch ₃ 2,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ H H 148 ch ₃ 3,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ H H 149 ch ₃ 3,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ H H 150 ch _{3 l-naphthyl-CH2} H H 151 ch _{3 2-naphthyl-CH2} H H 152 ch ₃ c ₆ h ₅ -ch (ch ₃ ) H H 153 ch ₃ 2-Cl-C ₆ H ₄ -CH (CH ₃₎ H H 154 ch ₃ 3-Cl-C ₆ H ₄ -CH (CH ₃₎ H H 155 ch ₃ 4-Cl-C ₆ H ₄ -CH (CH ₃ ) H hT 156 ch ₃ 2-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) H H 157 ch ₃ 3-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) H H 158 ch ₃ 4-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) H H 159 ch ₃ 2-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) H H 160 ch ₃ 3-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) H H 161 ch ₃ 4-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) H H 162 ch ₃ 2-tert-C ₄ H ₉ -C ₆ H ₄ -CH (CH ₃ ) H H 163 ch ₃ 3-tert-C ₄ H _g -C ₆ H ₄ -CH (CH ₃ ) H H 164 ch ₃ 4-tert-C ₄ H ₉ -C ₆ H ₄ -CH (CH ₃ ) H H 165 ch ₃ 2-CH ₃ OC ₆ H ₄ -CH (CH ₃ ) H H 166 ch ₃ 3-CH ₃ O-C ₈ H ₄ -CH (CH ₃ ) H H 167 ch ₃ 4-CH ₃ O-C ₈ H ₄ -CH (CH ₃ ) H H 168 ch ₃ 2-cyano-CGH ₄ -CH (CH ₃₎ H H 169 ch ₃ 3-cyano-CGH ₄ -CH (CH ₃₎ H H 170 ch ₃ 4-cyano-CGH ₄ -CH (CH ₃₎ H H 171 ch ₃ 2,4-Cl ₂ -C ₈ H ₃ -CH (CH ₃ ) H H 172 ch ₃ 3,4-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) H H 173 ch ₃ 3,5-Cl ₂ -C ₈ H ₃ -CH (CH ₃ ) H í H 174 ch ₃ 2,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH (CH ₃ ) H H

103

Table 6 - continued

Bile.

number R ¹ R ²

175 ch ₃ 2,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH (CH ₃ ) H H 176 ch ₃ CH ₃ OOC-CH ₂ H 177 ch ₃ c ₂ h ₅ ooc-ch ₂ 'H' H 178 ch ₃ 6-C ₃ H ₇ OOC-CH ₂ H H 179 : ch ₃ tert-C ₄ H ₉ OOC-CH ₂ H H 180 ch ₃ tert-C ₄ H _g OOC-CH (CH ₃ ) H H 181 ch ₃ N = C-CH ₂ : H H 182 ch ₃ c ₆ h ₅ co-ch ₂ H H 183 ch ₃ pyridin-2-ylmethyl H H 184 ch ₃ pyrazin-2-ylmethyl H H 185 ch ₃ pyrimidin-2-ylmethyl H C · ’ . H 186 ch ₃ fur-2-ylmethyl H H 187 ch ₃ pyrrol-2-ylmethyl H H 188 ch ₃ N-methylpyrrole-2-ylmethyl H H 189 ch ₃ thien-2-ylmethyl H H 190 ch ₃ isoxazol-5-ylmethyl H H 191 ch ₃ thiazol-2-ylmethyl H H 192 ch ₃ thiazol-5-ylmethyl H H 193 ch ₃ oxazol-2-ylmethyl H H 194 ch ₃ pyrazol-3-ylmethyl H H 195 ch ₃ benzofuran-2-ylmethyl H H 196 ch ₃ indol-2-ylmethyl H H 197 ch ₃ indol-3-ylmethyl H H 198 ch ₃ benzothiazol-2-ylmethyl H H 199 ch ₃ quinolin-2-ylmethyl H H 200 ch ₃ 4-ci-c ₆ h ₄ and (ch ₃ ) -ch ₂ H H 201 H H ^C 2 ^H 5 H 202 H ch ₃ ^C 2 ^H 5 H 203 H t-C ₄ H _g * ^C 2 ^H 5 H 204 H ch ₂ = ch-ch ₂ ^C 2 ^H 5 H

104

Table 6 - continued

Bile.

number R ¹ R ² R ⁴ R ⁶ 205 H CH ₂ = C (C1) -CH ₂ ^C 2 ^H 5 H 206 H ch ₂ = c (ch ₃ ) -ch ₂ 1 ^C 2 ^H 5 H 207 H ch ₃ ch = ch-ch ₂ ^C 2 ^H 5 H 208 H hocch ₂ ^C 2 ^H 5 H 209 H CH ₃ CsC-CH ₂ ^C 2 ^H 5 H 210 H cycloalkyl CGH · ^ ^C 2 ^H 5 H 211 H C ₆ ^H 5 -C 2 ^{H C} 2 ^H 5 H 212 H 2-FC ₆ H ₄ -CH ₂ ^C 2 ^H 5 H 213 H 3-FC ₆ H ₄ -CH ₂ ^C 2 ^H 5 H 214 H 4-FC ₆ ^h ₄ - ^CH 2 5 ', 2' H 215 H 2-Cl-C ₆ H ₄ CH ₂ ^C 2 ^H 5 H 216 H 3-Cl-C ₆ H ₄ CH ₂ ^C 2 ^H 5 H 217 H 4-Cl-C ₆ H ₄ CH ₂ ^C 2 ^H 5 H 218 H 2-Br-C ₆ H ₄ CH ₂ ^C 2 ^H 5 H 219 H 3-Br-C 8 H ₄ -CH ₂ ^C 2 ^H 5 H 220 H 4-Br-C ₆ H ₄ CH ₂ ^C 2 ^H 5 H 221 H 2-CH ₃ - ^C 6 ^H 4 -C 2 ^{H C} 2 ^H 5 H 222 H 3-CH ₃ - ^C 6 ^H 4 -C 2 ^H 5 ', 2' H 223 H 4-CH ₃ - ^c 6 ^H 4 ^-CH 2 ^C 2 ^H 5 H 224 H ² - ^CF 3 ^C 6 ^H 4 - ^CH 2 ^C 2 ^H 5 H 225 .H 3-CF ₃ - ^c 6 ^H 4 -CH 2 ^C 2 ^H 5 H 226 (H 4-CF ₃ ^-C 6 ^H 4 ^-c H2 ^C 2 ^H 5 H 227 H 2-iso-C ₃ H ₇ -C ₆ H ₄ -CH ₂ ^C 2 ^H 5 H 228 H 3-iso-C ₃ H ₇ -C ₆ H ₄ -CH ₂ ^C 2 ^H 5 H 229 H 4-iso-C ₃ H ₇ -C ₆ H ₄ -CH ₂ ^C 2 ^H 5 H 230 H 2-tert-C ₄ H ₉ -C ₈ H ₄ -CH ₂ ^C 2 ^H 5 H 231 H 3-tert-C ₄ H ₉ -C ₈ H ₄ -CH ₂ ^C 2 ^H 5 H 232 H 4-t-C ₄ H _{g 4 -CH2} -CgH ^C 2 ^H 5 H 233 H 2-CH ₃ O-C ₈ H ₄ -CH ₂ ^C 2 ^H 5 H 234 H 3-CH ₃ O-C ₈ H ₄ -CH ₂ 5 ', 2' H

105

Table 6 - continued

Bile.

number R ¹ R ² R ⁴ R ⁶ 235 H 4-CH ₃ OC ₆ H ₄ -CH ₂ ^C 2 ^H 5 H 236 H _2-cyano-4-CH CGH _second ^C 2 ^H ₅ H 237 H _{3-cyano-4-CH 2} CGH ^C 2 ^H 5 H 238 H _{4-cyano-4-CH 2} CGH ^C 2 ^H 5 H 239 H 2-nitro-C ₆ H ₄ CH ₂ ^C 2 ^H 5 H 240 H 3-nitro-C ₆ H ₄ CH ₂ ^C 2 ^H 5 H 241 H _{4-nitro-4-CGH CH2} ^C 2 ^H 5 H 242 H 2,4-Cl ₂ -C ₈ H ₃ -CH ₂ ^C 2 ^H 5 H 243 H 3,4-C 1 ₂ - ^C ₆ ^H 3 ^C H 2 ^C 2 ^H 5 H 244 H 3,5-Cl ₂ -C ₈ H ₃ -CH ₂ ^C 2 ^H 5 H 245 H 2,6-Cl ₂ -C ₈ H ₃ -CH ₂ T θ2 ≤ 5 H 246 H 2,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ ^C 2 ^H 5 H 247 H 2,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ ^C 2 ^H 5 H 248 H 3,4- (CH ₃ ) 2 ^-C 6 ^H 3 ^-CH 2 ^C 2 ^H 5 H 249 H 3,5- (C ^h ₃ ) ₂ - ^c 6 ^h 3- ^ch ₂ ^C 2 ^H 5 H 250 H _{l-naphthyl-CH2} ^C 2 ^H 5 H 251 H _{2-naphthyl-CH2} ^C 2 ^H 5 H 252 H CGH ₅ CH (CH ₃₎ ^C 2 ^H 5 H 2:53 H 2-Cl-CGH ₄ -CH (CH ₃₎ ^C 2 ^H 5 H 254 H 3-Cl-CGH ₄ -CH (CH ₃₎ ^C 2 ^H 5 H 255 H 4-Cl-C ₆ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 H 256 H 2-CH ₃ -C ₈ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 H 257 H 3-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 H 258 H 4-CH ₃ -C ₈ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 H 259 H 2-CF ₃ -C ₈ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 H 260 H 3-CF ₃ -C ₈ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 H 261 H 4-CF ₃ -C ₈ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 H 262 H 2-tert-C ₄ H ₉ -C ₈ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 H 263 H 3-tert-C ₄ H ₉ -C ₈ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 H 264 H 4-tert-C ₄ H ₉ -C ₈ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 H

106

Table 6 - continued

Bile.

number R ¹ R ² R ⁴ R ⁶ 265 H 2-CH ₃ OC ₆ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 H 266 H 3-CH ₃ OC ₆ H ₄ -CH (CH ₃ ), ^C 2 ^H 5 H 267 H 4-CH ₃ OC ₆ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 H 268 H 2-cyano-C ₆ H ₄ -CH (CH ₃₎ ^C 2 ^H 5 H 269 H 3-cyano-C ₆ H ₄ -CH (CH ₃₎ ^C 2 ^H p H 270 H 4-cyano-C ₆ H ₄ -CH (CH ₃₎ ^C 2 ^H 5 H 271 H 2,4-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) ^C 2 ^H 5 H 272 H 3,4-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) ^C 2 ^H 5 H 273 H 3,5-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) ^C 2 ^H 5 H 274 H 2,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH (CH ₃ ) ^C 2 ^H 5 H 275 H 2,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH (CH ₃ ) ^C 2 ^H 5 H 276 H ch ₃ ooc-ch ₂ ^C 2 ^H 5 H 277 H C ₂ H ₅ OOC-CH ₂ ^C 2 ^H 5 H 278 H o-c ₃ h ₇ ooc-ch ₂ ^C 2 ^H 5 H 279 H t-C ₄ H ₈ OOC-CH ₂ ^C 2 ^H 5 H 280 H tert-C ₄ H ₉ OOC-CH (CH ₃ ) ^C 2 ^H 5 H 281 H _NSC-CH2 ^C 2 ^H 5 H 282 H ^C 6 ^H 5 ^CO 2 ^CH 2 ^C 2 ^H 5 H 283 H pyridin-2-ylmethyl ^C 2 ^H 5 H 284 H pyrazin-2-ylmethy1 ^C 2 ^H 5 H 285 H pyrimidin-2-ylmethyl 5 ', 2' H 286 H fur-2-ylmethyl ^C 2 ^H 5 H 287 H pyrrol-2-ylmethyl ^C 2 ^H 5 H 288 H N-methylpyrrole-2-ylmethyl ^C 2 ^H 5 H 289 H thien-2-ylmethyl ^C 2 ^H 5 H 290 H i. oxazol-5-ylmethyl (5 ', 2' H 291 H thiazol-2-ylmethyl ^C 2 ^H 5 H 292 H thiazol-5-ylmethyl ^C 2 ^H 5 H 293 H oxazol-2-ylmethyl ^C 2 ^H 5 H 294 H pyrazol-3-ylmethyl ^C 2 ^ 5 H

107

Table 6 - continued

Bile.

number R ¹ R ² R ⁴ R ⁶ 295 H benzofuran-2-ylmethyl ^C 2 ^H 5 H 296 H indol-2-ylmethyl 1 ^C 2 ^H 5 H 297 H indol-3-ylmethyl ^C 2 ^ 5 H 298 H benzothiazol-2-ylmethyl ^C 2 ^H 5 H 299 H quinolin-2-ylmethyl ^C 2 ^H 5 H 300 H 4-ci-c ₆ h ₄ and (ch ₃ ) -ch ₂ ^C 2 ^H 5 H 301 ch ₃ H ^C 2 ^H 5 H 302 ch ₃ ch ₃ ^C 2 ^H 5 H 303 ch ₃ t-C ₄ Hg ^C 2 ^H 5 H 304 ch _{3 CH2-CH-CH2} ^C 2 ^H 5 H 305 ch ₃ CH ₂ = C (C 1) in CH ₂ ^C 2 ^H 5 H 306 ch ₃ CH ₂ = C (CH ₃ ) -CH ₂ ^C 2 ^H 5 H 307 ch ₃ ch ₃ ch = ch-ch ₂ ^C 2 ^H 5 H 308 ch ₃ HCsCCH ₂ ^C 2 ^H 5 H 309 ch ₃ CH ₃ CsC-CH ₂ ^C 2 ^H 5 H 310 ch ₃ cycloalkyl CgH- ^ ^C 2 ^H 5 H 311 ch ₃ ^C 6 ^H 5 ^CH 2 ^C 2 ^H 5 H 312 ch ₃ 2-FC ₆ H ₄ -CH ₂ * '2? 5 H 313 ch ₃ 3-FC ₆ H ₄ -CH ₂ ^C 2 ^H 5 H 314 ch ₃ ⁴ ~ ^fC 6 ^H 4 ^_CH 2 ^C 2 ^H 5 H 316 ch ₃ 3-Cl-C ₆ H ₄ CH ₂ ^C 2 ^H 5 H 317 ch ₃ 4-Cl-C ₆ H ₄ CH ₂ ^C 2 ^H 5 H 318 ch ₃ 2-Br-C ₆ H ₄ CH ₂ ^C 2 ^H 5 H 319 ch ₃ 3-Br-C ₆ H ₄ CH ₂ ^C 2 ^H 5 H 320 ch ₃ 4-Br-C ₆ H ₄ CH ₂ ^C 2 ^H 5 H 321 ch ₃ 2-CH ₃ ^-C 6 ^H 4 ^-c H2 ^C 2 ^H 5 H 322 ch ₃ 3-CH ₃ - ^c 6 ^H 4 ^-CH 2 ^C 2 ^H 5 H 323 ch ₃ 4-CH ₃ -C ₆ H ₄ -CH ₂ ^C 2 ^H 5 H 324 ch ₃ ^2-cf 3- ^C 6 ^H 4 ^-CH 2 ^C 2 ^H 5 H 325 ch ₃ ³ - ^CF 3 ^C 6 ^H 4 - ^CH 2 ^C 2 ^H 5 H

108

Table 6 - continued

Bile.

number R ¹ R ² R ⁴ R ⁶ 326 ch ₃ 4-CF ₃ -C ₆ H ₄ -CH ₂ ^C 2 ^H 5 H 327 ch ₃ 2-iso-C ₃ H ₇ -C ₆ H ₄ -CH ₂ ^C 2 ^H 5 H 328 ch ₃ 3-ISO-C ₃ H ₇ -C ₆ H ₄ -CH ₂ 5 ', 2' H 329 ch ₃ 4-iso-C ₃ H ₇ -C ₆ H ₄ -CH ₂ ^C 2 ^H 5 H 330 . ^CH 3 2-t-C ₄ H _{g 4 -CH2} -CgH ^C 2 ^H 5 H 331 ch ₃ 3-tert-C ₄ H ₈ -C ₆ H ₄ -CH ₂ ^C 2 ^H 5 H 332 ^CH 3 4-tert-C ₄ H ₉ -C ₆ H ₄ -CH ₂ ^C 2 ^H 5 H 333 ch ₃ 2-CH ₃ OC ₆ H ₄ -CH ₂ H 334 ^CH 3 3-CH ₃ OC ₆ H ₄ -CH ₂ ^C 2 ^H 5 H 335 ch ₃ 4-CH ₃ OC ₆ H ₄ -CH ₂ ^C 2 ^H 5 H 336 ch ₃ 2-cyano-C ₆ H ₄ -CH ₂ t) ^C 2 ^H 5 H 337 ^CH 3 _{3-cyano-4-CGH} CH2 ^C 2 ^H 5 H 338 ch ₃ 4-cyano-C ₆ H ₄ CH ₂ ^C 2 ^H 5 H 339 ch ₃ 2-nitro-C ₆ H ₄ CH ₂ ^C 2 ^H 5 H 340 ch _{3 3-nitro-4-CH 2} CGH ^C 2 ^H 5 H 341 ch ₃ 4-nitro-C ₆ H ₄ CH ₂ ^C 2 ^H 5 H 342 ch ₃ 2,4-Cl ₂ -C ₆ H ₃ ^-CH 2 ^C 2 ^H 5 H 343 ch ₃ ^3/4 - ^{C 1 2-C} 6 ^H 3 ^"CH 2 ^C 2 ^H 5 H 344 ch ₃ 3,5-C 1 _2-C ^3-C ₆ H 2 ^{hours C} 2 ^H 5 H 345 ^CH 3 2,6-Cl ₂ -C ₆ H ₃ -CH ₂ ^C 2 ^H 5 H 346 ch ₃ 2,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ ^C 2 ^H 5 . H 347 ch ₃ 2,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ ^C 2 ^H 5 í H 348 ^CH 3 3,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ ^C 2 ^H 5 H 349 ch ₃ 3,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ ^C 2 ^H 5 H 350 ch _{3 l-naphthyl-CH2} ^C 2 ^H 5 H 351 ch _{3 2-naphthyl-CH2} ^C 2 ^H 5 H 352 ch ₃ c ₆ h ₅ -ch (ch ₃ ) ^C 2 ^H 5 H 353 ch ₃ 2-Cl-C ₆ H ₄ -CH (CH ₃₎ ^C 2 ^H 5 H 354 ch ₃ 3-Cl-C ₆ H ₄ -CH (CH ₃₎ ^C 2 ^H 5 H 355 ch ₃ 4-Cl-C ₆ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 H

109

Table 6 - continued

Bile.

number R ¹ R ²

356 ch ₃ 2-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 H 357 ch ₃ ! 3-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 H 358 ch ₃ 4-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 H 359 ch ₃ 2-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 H 360 ch ₃ 3-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 H 361 ch ₃ 4-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 H 362 ch ₃ 2-tert-C ₄ H _g -C ₆ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 H 363 ch ₃ 3-tert-C ₄ H ₉ -C ₆ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 H 364 ch ₃ 4-tert-C ₄ H ₉ -C ₆ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 H 365 ch ₃ 2-CH ₃ OC ₆ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 H 366 ch ₃ 3 ^r CH ₃ OC ₆ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 H 367 ^CH 3 4-CH ₃ OC ₆ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 H 368 ch ₃ 2-cyano-C ₆ H ₄ -CH (CH ₃₎ ^C 2 ^H 5 H 369 ch ₃ 3-cyano-C ₆ H ₄ -CH (CH ₃₎ ^C 2 ^H 5 H 370 ch ₃ 4-cyano-C ₆ H ₄ -CH (CH ₃₎ ^C 2 ^H 5 H 371 ch ₃ 2,4-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) ^C 2 ^H 5 H 372 ch ₃ 3,4-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) ^C 2 ^H 5 H 373 ch ₃ 3,5-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) ^C 2 ^H 5 H 374 ch ₃ 2,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH (CH ₃ ) ^C 2 ^H 5 H 375 ch ₃ 2,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH (CH ₃ ) ^C 2 ^H 5 H 376 ch ₃ ch ₃ ooc-ch ₂ ^C 2 ^H 5 H 377 ch ₃ c ₂ h ₅ ooc-ch ₂ l · ^C 2 ^H 5 H 378 ch ₃ Ezo-C ₃ H ₇ OOC-CH ₂ ^C 2 ^H 5 H 379 ch ₃ tert-C ₄ H ₉ OOC-CH ₂ ^C 2 ^H 5 H 380 ch ₃ tert-C ₄ HgOOC-CH (CH ₃ ) ^C 2 ^H 5 H 381 ch ₃ n = c-ch ₂ ^C 2 ^H 5 H 382 ch ₃ c ₆ h ₅ co-ch ₂ ^C 2 ^H 5 H 383 ch ₃ pyridin-2-ylmethyl ^C 2 ^H 5 H 384 ch _{3 ΰ} pyrazin-2-ylmethy1 ^C 2 ^H 5 H 385 ch ₃ pyrimidin-2-ylmethyl ^C 2 ^H 5 H

110

jf

Á

-with

Table 6 - continuation of the merger.

number R ¹ R ²

386 ch ₃ fur-2-ylmethyl ^C 2 ^H 5 H 387 ch ₃ pyrrol-2-ylmethyl ^C 2 ^H 5 388 ch ₃ N-methylpyrrole-2-ylmethyl ^C 2 ^H 5 H 389 ch ₃ thien-2-ylmethyl ^C 2 ^H 5 H 390 ch ₃ isoxazol-5-ylmethyl ^C 2 ^H 5 H 391 ch ₃ thiazol-2-ylmethyl ^C 2 ^H 5 H 392 ch ₃ thiazol-5-ylmethyl ^C 2 ^H 5 H 393 ch ₃ oxazol-2-ylmethyl ^C 2 ^H 5 H 394 ch ₃ pyrazol-3-ylmethyl ^C 2 ^H 5 H 395 ch ₃ benzofuran-2-ylmethyl ^C 2 ^H 5 H 396 ch ₃ indol-2-ylmethyl ^C 2 ^H 5 H 397 ch ₃ indol-3-ylmethyl ^C 2 ^H 5 H 398 ch ₃ benzothiazol-2-ylmethyl ^C 2 ^H 5 H 399 ch ₃ quinolin-2-ylmethyl ^C 2 ^H 5 H 400 ch ₃ 4-Cl-C ₆ H ₄ OCH (CH ₃₎ CH ₂ ^C 2 ^H 5 H 401 H H H ch ₃ 402 H ch ₃ H ch ₃ 403 H t-C ₄ H _g H ch ₃ 404 H ch ₂ = ch-ch ₂ H ch ₃ 405 H ch ₂ = c (ci) -ch ₂ H ch ₃ 406 H ch ₂ = c (ch ₃ ) -ch ₂ H ch ₃ 407 H ch ₃ ch = ch-ch ₂ H ch ₃ 408 H HCsCCH ₂ H ch ₃ 409 H CH ₃ CsC-CH ₂ H ch ₃ 410 H cycloalkyl CGH -] ^ H ch ₃ 411 H c ₆ h ₅ -ch ₂ H ch ₃ 412 H ² - ^f - ^c 6 ^h 4-CH ₂ H ch ₃ 413 H 3-FC ₆ H ₄ -CH ₂ H ch ₃ 414 H 4-FC ₆ H ₄ -CH ₂ H ch ₃ 415 H 2-Cl-C ₆ H ₄ CH ₂ H ch ₃

111

Table 6 - continued

Bile.

number R ¹ R ² R ⁴ R ⁶ 416 H 3-Cl-C ₆ H ₄ CH ₂ H ch ₃ 417 H 4-Cl-C ₆ H ₄ CH ₂ H 1 ch ₃ 418 H 2-Br-C ₆ H ₄ CH ₂ H ch ₃ 419 H 3-Br-C ₆ H ₄ CH ₂ H ch ₃ 420 H 4-Br-C ₆ H ₄ CH ₂ H ch ₃ 421 H 2-CH ₃ -C ₆ H ₄ -CH ₂ H ch ₃ 422 H 3-CH ₃ -C ₆ ^H 4 ^CH 2 ¹ H ch ₃ 423 H 4-CH ₃ -C ₆ H ₄ -CH ₂ H ch ₃ 424 H 2-CF ₃ -C ₆ H ₄ -CH ₂ H ch ₃ 425 H 3-CF ₃ ^-C 6 ^H 4 ^-CH 2 H ch ₃ b 4 26 H 4-CF ₃ -C ₆ H ₄ -CH ₂ H ch ₃ 427 H 2-iso-C ₃ Hy-C ₈ H ₄ -CH ₂ H ch ₃ 428 H 3-iso-C ₃ H ₇ -C ₈ H ₄ -CH ₂ H ch ₃ 429 H 4-iso-C ₃ H ₇ -C ₆ H ₄ -CH ₂ H ch ₃ 430 H 2-tert-C ₄ H ₉ -C ₈ H ₄ -CH ₂ H ch ₃ 431 H 3-tert-C ₄ H ₉ -C ₈ H ₄ -CH ₂ H ch ₃ 432 H 4-t-C ₄ H _g C ₆ H ₄ CH ₂ H ch ₃ 433 H 2-CH ₃ OC ₆ H ₄ -CH ₂ H ch ₃ 434 H 3-CH ₃ OC ₆ H ₄ -CH ₂ H ch ₃ 435 H 4-CH ₃ O-C ₈ H ₄ -CH ₂ H ch ₃ 436 H _{2-cyano-4-CH 2} CGH H ch ₃ 437 H 3-cyano-CGH-CH ₂ H ch ₃ 438 H 4-cyano-c ₆ H ₄ -CH ₂ H ch ₃ 439 H _{2-nitro-4-CH 2} CGH H ch ₃ 440 H _{3-nitro-4-CH 2} CGH H ch ₃ 441 H _{4-nitro-4-CH 2} CGH H ch ₃ 442 H 2,4-Cl ₂ -C ₆ H ₃ -CH ₂ H ch ₃ 443 H 3,4-Cl ₂ -C ₆ ^h ₃ -CH ₂ H ch ₃ 444 H 3,5-Cl ₂ -C ₆ H ₃ -CH ₂ H ch ₃ 445 H 2,6-Cl ₂ -C ₆ H ₃ -CH ₂ H ch ₃

112

Table 6 - continued

Bile. number

446 H 2,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ H ch ₃ 447 H 2,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ ! ^H ch ₃ 448 H 3,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ H ch ₃ 449 H 3,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ H ch ₃ 450 H _{l-naphthyl-CH2} H ch ₃ 451 H _{2-naphthyl-CH2} H ch ₃ 452 H c ₆ h ₅ -ch (ch ₃ ) H ch ₃ 453 H 2-Cl-C ₆ H ₄ -CH (CH ₃₎ H ch ₃ 454 H 3-Cl-C ₆ H ₄ -CH (CH ₃₎ H ch ₃ 455 H 4-Cl-C ₆ H ₄ -CH (CH ₃ ) H ch ₃ 456 H 2-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) H '' ' ch ₃ 457 H 3-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) H ch ₃ 458 H 4-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) H ch ₃ 459 H 2-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) H ch ₃ 460 H 3-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) H ^CH 3 461 H 4-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) H ch ₃ 462 H 2-tert-C ₄ H ₉ -C ₆ H ₄ -CH (CH ₃ ) H ch ₃ 463 H 3-tert-C ₄ H ₉ -C ₆ H ₄ -CH (CH ₃ ) H ch ₃ 464 H 4-t-C ₄ H _9, -C _g H ₄ -CH (CH ₃₎ H ch ₃ 465 H 2-CH ₃ OC ₆ H ₄ -CH (CH ₃ ) H ch ₃ 466 H 3-CH ₃ OC ₆ H ₄ -CH (CH ₃ ) H ch ₃ 467 H 4-CH ₃ OC ₆ H ₄ -CH (CH ₃ ) H ch ₃ 468 H 2-cyano-C ₆ H ₄ -CH (CH ₃₎ H ch ₃ 469 H 3-cyano-C ₆ H ₄ -CH (CH ₃₎ H ch ₃ 470 H 4-cyano-C ₆ H ₄ -CH (CH ₃₎ H ch ₃ 471 H 2,4-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) H ch ₃ 472 H 3,4-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) H ch ₃ 473 H 3,5-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) H ch ₃ 474 H 2,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH (CH ₃ ) H ch ₃ 475 H 2,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH (CH ₃ ) H ch ₃

113

Table 6 - continued

Bile.

number R ¹ R ² R ⁴ R ⁶ 476 H CH ₃ OOC-CH ₂ H ch ₃ 477 | H C ₂ H ₅ OOC-CH ₂ H ch ₃ 478 H Igo-C ₃ H ₇ OOC-CH ₂ H ch ₃ 479 H tert-C ₄ H ₉ OOC-CH ₂ H ch ₃ 480 H tert-C ₄ H ₉ OOC-CH (CH ₃ ) H ch ₃ 481 H n = c-ch ₂ 'i H ch ₃ 482 H c ₆ h ₅ co-ch ₂ ⁵ H ch ₃ 483 H pyridin-2-ylmethyl H ch ₃ 484 H pyrazin-2-ylmethyl H ch ₃ 485 H pyrimidin-2-ylmethyl H ch ₃ 486 73 H fur-2-ylmethyl H ch ₃ 487 H pyrrol-2-ylmethyl H ch ₃ 488 H N-methylpyrrole-2-ylmethyl H ch ₃ 489 H thien-2-ylmethyl H ch ₃ 490 H isoxazol-5-ylmethyl H ^CH 3 491 H thiazol-2-ylmethyl H ch ₃ 492 H thiazol-5-ylmethyl H ch ₃ 493 H oxazol-2-ylmethyl H ch ₃ 494 H pyrazol-3-ylmethyl H ch ₃ 495 H benzofuran-2-ylmethyl H ch ₃ 496 H Indol-2-ylmethyl: H ch ₃ 497 H Indol-3-ylmethyl * H ch ₃ 498 H benzothiazol-2-ylmethyl H ch ₃ 499 H quinolin-2-ylmethyl H ch ₃ 500 H 4-ci-c ₆ h ₄ and (ch ₃ ) -ch ₂ H ch ₃ 501 ch ₃ H H ch ₃ 502 ch ₃ ch ₃ H ch ₃ 503 ch ₃ t-C ₄ H ₉ H ch ₃ 504 ch ₃ ch ₂ = ch-ch ₂ H ch ₃ 505 ch ₃ ch ₂ = c (c 1) -ch ₂ H ch ₃

114

Table 6 - continued

Bile.

number R ¹ R ² R ⁴ R ⁶ 506 ch ₃ CH ₂ = C (CH ₃ ) -CH ₂ H ch ₃ 507 ch ₃ CH = CH-CH-CH ~ 3 z | H ch ₃ 508 ch ₃ hc = cch ₂ H ch ₃ 509 ch ₃ CH ₃ C = c-CH ₂ H ch ₃ 510 ch ₃ cycloalkyl CGH ^ J ^ H ch ₃ 511 ch ₃ ^C 6 ^H 5 ^CH 2 H ^CH 3 512 ch ₃ 2-FC ₆ H ₄ -CH ₂ H ch ₃ 513 ch ₃ 3-F-C 8 H ₄ -CH ₂ H ch ₃ 514 ^Objective 3 4-FC ₆ H ₄ -CH ₂ 'H ch ₃ 515 ch ₃ 2-Cl-C ₆ H ₄ CH ₂ H ch ₃ 516 ch ₃ 3-ci-c ₆ h ₄ -ch ₂ T H ch ₃ 517 ch ₃ 4-Cl-C ₆ H ₄ CH ₂ H ch ₃ 518 ch ₃ 2-Br-C ₆ H ₄ CH ₂ H ch ₃ 519 ch ₃ 3-Br-C ₆ H ₄ CH ₂ H ch ₃ 520 ch ₃ 4-Br-C ₆ H ₄ CH ₂ H ch ₃ 521 ch ₃ 2-CH ₃ -C ₆ H ₄ -CH ₂ H ch ₃ 522 ch ₃ 3-CH ₃ -C ₆ H ₄ -CH ₂ H ch ₃ 523 ch ₃ 4-CH ₃ -C ₆ H ₄ -CH ₂ H ch ₃ 524 ch ₃ ² -CF ₃ ^-C 6 ^H 4 ^-CH 2 H ch ₃ 525 ch ₃ 3-CF ₃ -C ₆ H ₄ -CH ₂ H ch ₃ 526 ch ₃ 4-CF ₃ - ^C 6 ^H 4 _{C 2} H H ch ₃ 527 ch ₃ 2-Azo-C ₃ H ₇ -C ₆ H ₄ -CH ₂ H ch ₃ 528 ch ₃ 3 “1Ζθ ^- ΟβΗ · 7“ Ο ^ Η ^ ^- CH 2 H ch ₃ 529 ch ₃ 4-iso-C ₃ H ₇ -C ₆ H ₄ -CH ₂ H ch ₃ 530 ch ₃ 2-tert-C ₄ H ₉ -C ₆ H ₄ -CH ₂ H ch ₃ 531 ch ₃ 3-t-C ₄ H _g C ₆ H ₄ CH ₂ H ch ₃ 532 ch ₃ 4-tert-C ₄ H ₉ -C ₆ H ₄ -CH ₂ H ch ₃ 533 ch ₃ 2-CH ₃ OC ₆ H ₄ -CH ₂ H ch ₃ 534 ch ₃ 3-CH ₃ OC ₆ H ₄ -CH _2; H ch ₃ 535 ch ₃ 4-CH ₃ O-C ₆ H ₄ -CH ₂ H ch ₃

115

Table 6 - continued

Bile.

number R ¹ R ² R ⁴ R ⁶ 536 ch _{3 2-cyano-4-CH 2} CGH H ch ₃ 537 ^C ₍ ^H 3 _{3-cyano-4-CH 2} CGH H ch ₃ 538 c'h ₃ 4 'cyan-CgH ₄ ' CH ₂ H ch ₃ 539 ch _{3 2-nitro-4-CH 2} CGH H ch ₃ 540 ch _{3 3-nitro-4-CGH CH2} H ch ₃ 541 ch _{3 4-nitro-4-CH 2} CGH H ch ₃ 542 ch ₃ ² ' ^4-cl 2' ^c 6 ^H 3 ^-CH 2 H ch ₃ 543 ch ₃ 3,4-Cl ₂ -C ₆ H ₃ -CH ₂ H ch ₃ 544 ch ₃ 3,5-Cl ₂ -C ₆ H ₃ -CH ₂ H ch ₃ 545 ch ₃ 2,6-Cl ₂ -C ₈ H ₃ -CH ₂ H ch ₃ 546 ch ₃ Ť 2,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ H ch ₃ 547 ch ₃ 2,5- (CH ₃ ) ₂ -C ₆ ^h 3 ^-CH 2 H ch ₃ 548 ch ₃ 3 _of 4- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ H ch ₃ 549 ch ₃ 3,5- (CH ₃ ) ₂ -C ₈ H ₃ -CH ₂ H ch ₃ 550 ch _{3 l-naphthyl-CH2} H ch ₃ 551 ch _{3 2-naphthyl-CH2} H ch ₃ 552 ch ₃ c ₆ h ₅ -ch (ch ₃ ) H ch ₃ 553 ch ₃ 2-Cl-CGH ₄ -CH (CH ₃₎ H ch ₃ 554 ch ₃ 3-Cl-CGH ₄ -CH (CH ₃₎ H ch ₃ 555 ch ₃ 4-Cl-C ₆ H ₄ -CH (CH ₃ ) H ch ₃ 556 ch ₃ 2-CH ₃ -C ₈ H ₄ -CH (CH ₃ ). H ch ₃ 557 ch ₃ 3-CH ₃ -C ₈ H ₄ -CH (CH ₃ ) - H ch ₃ 558 ch ₃ 4-CH ₃ -C ₈ H ₄ -CH (CH ₃ ) H ch ₃ 559 ch ₃ 2-CF ₃ -C ₈ H ₄ -CH (CH ₃ ) H ch ₃ 560 ch ₃ 3-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) H ch ₃ 561 ^CH 3 4-CF ₃ -C ₈ H ₄ -CH (CH ₃ ) H ch ₃ 562 ch ₃ 2-tert-C ₄ H ₉ -C ₆ H ₄ -CH (CH ₃ ) H ch ₃ 563 ch ₃ 3-tert-C ₄ H ₉ -C ₆ H ₄ -CH (CH ₃ ) H ch ₃ 564 _with CH ₃ 4-tert-C ₄ H ₉ -C ₈ H ₄ -CH (CH ₃ ) H ch ₃ 565 ch ₃ 2-CH ₃ O-C ₈ H ₄ -CH (CH ₃ ) H ch ₃

116

Table 6 - continued

Bile.

number R ¹ R ² R ⁴ R ⁶ 566 ch ₃ 3 'CH ₃ OC ₆ H ₄ -CH (CH ₃ ) H ch ₃ 567 1 ch ₃ 4-CH ₃ OC ₆ H ₄ -CH (CH ₃ ) H ch ₃ 568 ch ₃ 2-cyano-C ₆ H ₄ -CH (CH ₃₎ H ch ₃ 569 ch ₃ 3-cyano-C ₆ H ₄ -CH (CH ₃₎ H ch ₃ 570 ch ₃ 4-cyano-C ₆ H ₄ -CH (CH ₃₎ H ch ₃ 571 ch ₃ 2,4-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) 'H ch ₃ 572 ch ₃ 3,4-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) H ch ₃ 573 ch ₃ 3,5-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) H ch ₃ 574 ch ₃ 2,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH (CH ₃ ) H ch ₃ 575 ch ₃ 2,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH (CH ₃ ) H ch ₃ 576 T • ch ₃ ch ₃ ooc-ch ₂ H ch ₃ 577 ch ₃ C ₂ H ₅ OOC-CH ₂ H ch ₃ 578 ch ₃ i. oC ₃ H ₇ OOC-CH ₂ H ch ₃ 579 ch ₃ t-C ₄ H ₈ OOC-CH ₂ H ch ₃ 580 ch ₃ tert-C ₄ H _g OOC-CH (CH ₃ ) H ch ₃ 581 ch ₃ n = c-ch ₂ H ch ₃ 582 ch ₃ c ₆ h ₅ co-ch ₂ H ch ₃ 583 ch ₃ pyridin-2-ylmethyl H ch ₃ 584 ch ₃ pyrazin-2-ylmethyl H ch ₃ 585 ch ₃ pyrimidin-2-ylmethyl H ch ₃ 586 ch ₃ fur-2-ylmethyl H ch ₃ 587 ch ₃ { pyrrol-2-ylmethyl ·. H ch ₃ 588 ch ₃ N-methylpyrrole-2-ylmethyl H ch ₃ 589 ch ₃ thien-2-ylmethyl H ch ₃ 590 ch ₃ oxazol-5-ylmethyl H ch ₃ 591 ch ₃ thiazol-2-ylmethyl H ch ₃ 592 ch ₃ thiazol-5-ylmethyl H ch ₃ 593 ch ₃ oxazol-2-ylmethyl H ch ₃ 594 ch ₃ pyrazol-3-ylmethyl H ch ₃ 595 ch ₃ benzofuran-2-ylmethyl H ch ₃

117

Table 6 - continued

Bile.

number R ¹ R ²

596 ch ₃ indol-2-ylmethyl H ch ₃ 597 ch ₃ indol-3-ylmethyl H ch ₃ 598 ch ₃ benzothiazol-2-ylmethyl H ch ₃ 599 ch ₃ quinolin-2-ylmethyl H ch ₃ 600 ch ₃ 4-ci-c ₆ h ₄ and (ch ₃ ) -ch ₂ H ch ₃ 601 H H ^C 2 ^H 5 ch ₃ 602 H ch ₃ ^C 2 ^H 5 ch ₃ 603 H tert. ~ C ₄ H ₉ ^C 2 ^H 5 ch ₃ 604 H ch ₂ = ch-ch ₂ ^C 2 ^H 5 ch ₃ 605 H ch ₂ = c (ci) -ch ₂ ^C 2 ^H 5 ch ₃ 606 H ch ₂ = c (ch ₃ ) -ch ₂ 5 ', 2' C ^h ₃ 607 H ch ₃ ch = ch-ch ₂ ^C 2 ^H 5 ch ₃ 608 H hc = cch ₂ ^C 2 ^H 5 ch ₃ 609 H ch ₃ c = c-ch ₂ ^C 2 ^H 5 ch ₃ 610 H cyclo-C ₆ H ₁₃ ^C 2 ^H 5 ch ₃ 611 H ^C 6 ^H 5 ^CH 2 ^C 2 ^H 5 ch ₃ 612 H 2-FC ₆ H ₄ -CH ₂ ^c ₂ ^H 5 ch ₃ 613 H 3-FC ₆ H ₄ -CH ₂ C ₂ ^h p ch ₃ 614 H 4-FC ₆ H ₄ -CH ₂ ^C 2 ^H 5 ch ₃ 615 H 2-Cl-C ₆ H ₄ CH ₂ ^C 2 ^H 5 ch ₃ 616 H 3-Cl-C ₆ H ₄ CH ₂ ^C 2 ^H 5 ch ₃ 617 H 4-Cl-C ₆ H ₄ CH ₂ ^C 2 ^H 5 ch ₃ 618 H 2-Br-C ₆ H ₄ CH ₂ ^C 2 ^H 5 ch ₃ 619 H 3-Br-C ₆ H ₄ CH ₂ ^C 2 ^H 5 ch ₃ 620 H 4-Br-C ₆ H ₄ CH ₂ ^C 2 ^H 5 ch ₃ 621 H 2-CH ₃ -C 6 ^H 4 ^C ₂ H ^C 2 ^H 5 ch ₃ 622 H 3-CH ₃ ^-C 6 ^H 4 ^-CH 2 ^C 2 ^H 5 ch ₃ 623 H 4-CH ₃ -C ₆ H ₄ -CH ₂ ^C 2 ^H 5 ch ₃ 624 H 2-CF ₃ -C ₆ ^H 4 ^-CH 2 ^C 2 ^H 5 ch ₃ 625 H 3-CF ₃ - ^C 6 ^H 4 ^-ch ₂ ^C 2 ^H 5 ch ₃

118

Table 6 - continued

Bile.

number R ¹ R ²

626 H 4-CF ₃ -C ₆ H ₄ -CH ₂ ^C 2 ^H 5 ch ₃ 627 H 2-iso-C ₃ H ₇ -C ₆ H ₄ -CH ₂ ^C 2 ^H 5 ch ₃ 628 H 3-iso-C ₃ H ₇ -C ₈ H ₄ -CH ₂ ^C 2 ^H 5 ch ₃ 629 H 4-iso-C ₃ H ₇ -C ₈ H ₄ -CH ₂ ^C 2 ^H 5 ch ₃ 630 H 2-t-C ₄ H _g C ₆ H ₄ CH ₂ ^C 2 ^H 5 ch ₃ 631 H 3-tert-C ₄ H ₉ -C ₆ H ₄ -CH ₂ ^C 2 ^H 5 ch ₃ 632 H 4-tert-C ₄ H ₉ -C ₆ H ₄ -CH ₂ ^C 2 ^H 5 ch ₃ 633 H 2-CH ₃ OC ₆ H ₄ -CH ₂ ^C 2 ^H 5 ch ₃ 634 H 3-CH ₃ OC ₆ H ₄ -CH ₂ ^C 2 ^H 5 ch ₃ 635 H 4-CH ₃ OC ₆ H ₄ -CH ₂ ^C 2 ^H 5 ch ₃ 636 H 2-cyano-C ₆ H ₄ CH ₂ ^C 2 ^H 5 ch ₃ 637 H _{3-cyano-4-CH 2} CGH ^C 2 ^H 5 ch ₃ 638 H 4-cyano-C ₆ H ₄ CH ₂ ^C 2 ^H 5 ch ₃ 639 H 2-nitro-C ₆ H ₄ CH ₂ 5 ', 2' ch ₃ 640 H _{3-nitro-4-CH 2} CGH ^C 2 ^H 5 ch ₃ 641 H 4-nitro-C ₆ H ₄ CH ₂ 5 ', 2' ch ₃ 642 H 2,4-Cl ₂ -C ₆ H ₃ -CH ₂ ^C 2 ^H 5 ch ₃ 643 H 3,4-Cl ₂ -C ₆ H ₃ -CH ₂ ^C 2 ^H 5 ch ₃ 644 H 3,5-Cl ₂ -C ₆ H ₃ -CH ₂ ^C 2 ^H 5 ch ₃ 645 H 2,6-21 ₂ -Ο ₆ Η3 ^ ^Η 2 ^C 2 ^H 5 ch ₃ 646 H 2,4 - (^ 3) ^ 2-3-¾ ^C 2 ^H 5 ch ₃ 647 H 2,5½CH ₃ ) 2 ^-C 6 ^H 3 ^-CH 2 ^C 2 ^H 5 ch ₃ 648 H 3,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ ^C 2 ^H 5 ch ₃ 649 H 3,5- _(CH3) 2 ^_C 6 ^H 3 ^"CH 2 ^C 2 ^H 5 ch ₃ 650 H _{1-naphthyl-CH2} ^C 2 ^H 5 ch ₃ 651 H _{2-naphthyl-CH2} ^C 2 ^H 5 ch ₃ 652 H c ₆ h ₅ -ch (ch ₃ ) ^C 2 ^H 5 ch ₃ 653 H 2-Cl-C ₆ H ₄ -CH (CH ₃₎ ^C 2 ^H 5 ch ₃ 654 H 3-C 1-C ₆ H ₄ -CH (CH ₃₎ ^C 2 ^H 5 ch ₃ 655 H 4-Cl-C ₆ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 ch ₃

119

Table 6 - continued

Bile.

: ÍS1O R ¹ R ² R ⁴ R ⁶ 656 H 2-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 ch ₃ 657 H 3-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 ch ₃ 658 H 4-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) ^C 2 ^ 5 ch ₃ 659 H 2-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 ch ₃ 660 H 3-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) 5 ', 2' ch ₃ 661 H 4-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 ch ₃ 662 H 2-tert-C ₄ H ₉ -C ₆ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 ch ₃ 663 H 3-tert-C ₄ H ₉ -C ₆ H ₄ 'CH (CH ₃ ) ^C 2 ^H 5 ch ₃ 664 H 4-tert-C ₄ H _g -C ₆ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 ch ₃ 665 H 2-CH ₃ OC ₆ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 ch ₃ 666 H 3-CH ₃ OC ₆ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 ch ₃ 667 H 4-CH ₃ OC ₆ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 ch ₃ 668 H 2-cyano-C ₆ H ₄ -CH (CH ₃₎ 5 ', 2' ch ₃ 669 H 3-cyano-C ₆ H ₄ -CH (CH ₃₎ ^C 2 ^H 5 ch ₃ 670 H 4-cyano-C ₆ H ₄ -CH (CH ₃₎ ^C 2 ^H 5 ch ₃ 671 H 2,4-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) ^C 2 ^H 5 ch ₃ 672 H 3,4-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) ^C 2 ^H 5 ch ₃ 673 H 3,5-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) ^C 2 ^H 5 ch ₃ 674 H 2,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH (CH ₃ ) ^C 2 ^H 5 ch ₃ 675 H 2,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH (CH ₃ ) ^C 2 ^H 5 ch ₃ 676 H ; ch ₃ ooc-ch ₂ ^C 2 ^H 5 ch ₃ 677 H 1 C ₂ H ₅ OOC-CH ₂ ^C 2 ^H 5 ^CH 3 678 H C ₃ H ₇ OOC-CH ₂ ^C 2 ^H 5 ch ₃ 679 H tert-C ₄ H ₉ OOC-CH ₂ ^C 2 ^H 5 ch ₃ 680 H tert-C ₄ H ₉ OOC-CH (CH ₃ ) ^C 2 ^H 5 ch ₃ 681 H _NSC-CH2 ^C 2 ^H 5 ch ₃ 682 H c ₆ h ₅ co-ch ₂ ^C 2 ^H 5 ch ₃ 683 H pyridin-2-ylmethyl ^C 2 ^H 5 ch ₃ 684 H pyrazin-2-ylmethyl ^C 2 ^H 5 ch ₃ 685 H pyrimidin-2-ylmethyl ^C 2 ^H 5 ch ₃

120

Table 6 - continued

Key, number

686 H fur-2-ylmethyl ^C 2 ^H 5 ch ₃ 687 H pyrrol-2-ylmethyl ^C 2 ^H 5 ch ₃ 688 H N-methylpyrrole-2-ylmethyl ^C 2 ^H 5 ch ₃ 689 H thien-2-ylmethyl ^C 2 ^H 5 ch ₃ 690 H isoxazol-5-ylmethyl ^C 2 ^H 5 ch ₃ 691 H thiazol-2-ylmethyl ^C 2 ^H 5 ch ₃ 692 H thiazol-5-ylmethyl ^C 2 ^H 5 ch ₃ 693 H oxazol-2-ylmethyl ^C 2 ^H 5 ch ₃ 694 H pyrazol-3-ylmethyl ^C 2 ^H 5 ch ₃ 695 H benzofuran-2-ylmethyl ^C 2 ^H 5 ch ₃ 696 H indol-2-ylmethyl ^C 2 ^H 5 ch ₃ 697 H indol-3-ylmethyl ^C 2 ^H 5 ch ₃ 698 H benzothiazol-2-ylmethyl ^C 2 ^H 5 ch ₃ 699 H quinolin-2-ylmethyl ^C 2 ^H 5 ch ₃ 700 H 4-ci-c ₆ h ₄ and (ch ₃ ) -ch ₂ * '2? 5 ch ₃ 701 ch ₃ H 5 ', 2' ch ₃ 702 ch ₃ ch ₃ ^C 2 ^H 5 ch ₃ 703 ch ₃ t-C ₄ H _g ^C 2 ^H 5 ch ₃ 704 ch ₃ ch ₂ = ch-ch ₂ ^C 2 ^H 5 ch ₃ 705 ch ₃ CH ₂ = C (C1) -CH ₂ ^C 2 ^H 5 ch ₃ 706 ch ₃ CH ₂ = C (CH ₃ ) -CH ₂ ^C 2 ^H 5 ch ₃ 707 ch ₃ ch ₃ ch = ch-ch ₂ ^C 2 ^H 5 ch ₃ 708 ch ₃ HC = CH ₂ ^C 2 ^H 5 ch ₃ 709 ch ₃ ch ₃ c = c-ch ₂ ^C 2 ^H 5 ch ₃ 710 ch ₃ cycloalkyl CgH- ^ ^C 2 ^H 5 ch ₃ 711 ch ₃ ^C 6 ^H 5 ^CH 2 ^C 2 ^H 5 ch ₃ 712 ch ₃ 2-FC ₆ H ₄ -CH ₂ ^C 2 ^H 5 ch ₃ 713 ch ₃ 3-FC ₆ H ₄ -CH ₂ ^C 2 ^H 5 ch ₃ 714 ch ₃ ^4-FC 6 ^H 4 ^-CH 2 ^C 2 ^H 5 ch ₃ 715 ch ₃ 2-Cl-C ₆ H ₄ CH ₂ ^C 2 ^H 5 ch ₃

121

Table 6 - continued

Cmpd

: number R ¹ R ² R ⁴ R ⁶ 716 ch ₃ 3-Cl-C ₆ H ₄ CH ₂ ^C 2 ^H 5 ch ₃ 717 ch ₃ 4-Cl-C ₆ H ₄ CH ₂ ^C 2 ^H 5 ch ₃ 718 ch ₃ 2-Br-C ₆ H ₄ CH ₂ 5 ', 2' ch ₃ 719 ch ₃ 3-Br-C ₆ H ₄ CH ₂ ^C 2 ^H 5 ch ₃ 720 ch ₃ 4-Br-C ₆ H ₄ CH ₂ ^C 2 ^H 5 ch ₃ 721 ch ₃ 2-CH ₃ -C ₆ H ₄ -CH ₂ ^C 2 ^H 5 ch ₃ 722 ch ₃ 3-CH ₃ ^-C 6 ^H 4 ^-ch ₂ ^C 2 ^H 5 ch ₃ 723 ch ₃ 4-CH ₃ -C ₆ H ₄ -CH ₂ ^C 2 ^H 5 ch ₃ 724 ch ₃ 2-CF ₃ ^-C 6 ^H ₄ ^-CH 2 ^C 2 ^H 5 ch ₃ 725 ch ₃ 3-CF ₃ -C ₆ H ₄ -CH ₂ ^C 2 ^H 5 ch ₃ 726 ch ₃ 4-CF ₃ -C ₆ H ₄ -CH ₂ ^C 2 ^H 5 ch ₃ 727 ch ₃ 2-iso-C ₃ H ₇ -C ₆ H ₄ -CH ₂ ^C 2 ^H 5 ch ₃ 728 ch ₃ . 3-ISO-C ₃ H ₇ -C ₆ H ₄ -CH ₂ ^C 2 ^H 5 ch ₃ 729 ch ₃ 4-IZO-C ₃ H ₇ - C ₆ H ₄ 'CH ₂ ^C 2 ^H 5 ch ₃ 730 ch ₃ 2-t-C ₄ H _g C ₆ H ₄ CH ₂ ^C 2 ^H 5 ch ₃ 731 ch ₃ 3-tert-C ₄ H ₈ -C ₆ H ₄ -CH ₂ ^C 2 ^H 5 ch ₃ 732 ch ₃ 4-tert-C ₄ H ₈ -C ₆ H ₄ -CH ₂ ^C 2 ^H 5 ch ₃ 733 ch ₃ 2-CH ₃ OC ₆ H ₄ -CH ₂ ^C 2 ^H 5 ch ₃ 734 ch ₃ 3-CH ₃ OC ₆ H ₄ -CH ₂ ^C 2 ^H 5 ch ₃ 735 ch ₃ 4-CH ₃ OC ₆ H ₄ -CH ₂ ^C 2 ^H 5 ch ₃ 736 _: ch _{3 2-cyano-4-CH 2} CGH ^C 2 ^H 5 ch ₃ 737 i ch ₃ 3-cyano-C ₆ H ₄ -CH ₂ ^C 2 ^H 5 ch ₃ 738 ch _{3 4-cyano-4-CGH CH2} ^C 2 ^H 5 ch ₃ 739 ch _{3 2-nitro-4-CH 2} CGH ^C 2 ^H 5 ch ₃ 740 ch ₃ 3-nitro-C ₆ H ₄ 'CH ₂ ^C 2 ^H 5 ch ₃ 741 ch _{3 4-nitro-4-CH 2} CGH ^C 2 ^H 5 ch ₃ 742 ch ₃ 2,4-Cl ₂ -C ₆ H ₃ -CH ₂ ^C 2 ^H 5 ch ₃ 743 ch ₃ 3,4-Cl ₂ -C ₆ H ₃ -CH ₂ ^C 2 ^H 5 ch ₃ 744 ch ₃ 3,5-Cl ₂ -C ₆ H ₃ -CH ₂ ^C 2 ^H 5 ch ₃ 745 ch ₃ 2,6-Cl ₂ -C ₆ H ₃ -CH ₂ ^C 2 ^H 5 ch ₃

122

Table 6 - continued

Bile. number

746 ch ₃ 2,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ ^C 2 ^H 5 ch ₃ 747 ch ₃ 2,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ ^C 2 ^H 5 ch ₃ 748 ch ₃ 3,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ ^C 2 ^H 5 ch ₃ 749 ch ₃ 3,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ ^C 2 ^H 5 ch ₃ 750 ch _{3 1-naphthyl-CH2} ^C 2 ^H 5 ch ₃ 751 ch ₃ 2-naphthyl-CH ₂ ^C 2 ^H 5 ch ₃ 752 ch ₃ c ₆ h ₅ -ch (ch ₃ ) ^C 2 ^H 5 ch ₃ 753 ch ₃ 2-Cl-C ₆ H ₄ -CH (CH ₃₎ ^C 2 ^H 5 ch ₃ 754 ch ₃ 3-Cl-C ₆ H ₄ -CH (CH ₃₎ ^C 2 ^H 5 ch ₃ 755 ch ₃ 4-Cl-C ₆ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 ch ₃ 756 ch ₃ 2-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 ch ₃ 757 ch ₃ 3-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 ch ₃ 758 ch ₃ 4-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 ch ₃ 759 ch ₃ 2-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 ch ₃ 760 ch ₃ 3-CF ₃ -C ₈ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 ch ₃ 761 ch ₃ 4-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 ch ₃ 762 ch ₃ 2-tert-C ₄ H ₉ -C ₆ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 ch ₃ 763 ch ₃ 3-tert-C ₄ H ₉ -C ₆ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 ch ₃ 764 ch ₃ 4-tert-C ₄ H ₉ -C ₆ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 ch ₃ 765 ch ₃ 2-CH ₃ OC ₆ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 ch ₃ 766 ch ₃ 3-CH ₃ OC ₆ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 ch ₃ 767 ch ₃ 4-CH ₃ OC ₆ H ₄ -CH (CH ₃ ) ^C 2 ^H 5 ch ₃ 768 ch ₃ 2-cyano-C ₆ H ₄ -CH (CH ₃₎ ^C 2 ^H 5 ch ₃ 769 ch ₃ 3-cyano-C ₆ H ₄ -CH (CH ₃₎ ^C 2 ^H 5 ch ₃ 770 ch ₃ 4-cyano-C ₆ H ₄ -CH (CH ₃₎ ^C 2 ^H 5 ch ₃ 771 ch ₃ 2,4-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) ^C 2 ^H 5 ch ₃ 772 ch ₃ 3,4-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) ^C 2 ^H 5 ch ₃ 773 ch ₃ 3,5-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) θ2 ≤ 5 ch ₃ 774 ch ₃ 2,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH (CH ₃ ) ^C 2 ^H 5 ch ₃ 775 ch ₃ 2,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH (CH ₃ ) ^C 2 ^H 5 ch ₃

123

Table 6 - continued

Bile.

number R ¹ R ² R ⁴ R ⁶ 776 ch ₃ CH ₃ OOC 'CH ₂ ^C 2 ^H 5 ch ₃ 777 ^CIi 3 c ₂ h ₅ ooc-ch ₂ ^C 2 ^H 5 ch ₃ 778 ch ₃ o-c ₃ h ₇ ooc-ch ₂ ^C 2 ^H 5 ch ₃ 779 ch ₃ tert-C ₄ H ₉ OOC-CH ₂ ^C 2 ^H 5 ch ₃ 780 ch ₃ tert-C ₄ H _g OOC-CH (CH ₃ ) ^C 2 ^H 5 ch ₃ 781 ch ₃ n ^ c-ch ₂ ^C 2 ^ 5 ^CH 3 782 ch ₃ c ₆ h ₅ co-ch ₂ ^C 2 ^H 5 ch ₃ 783 ch ₃ pyridin-2-ylmethyl ^C 2 ^H 5 ch ₃ 784 ch ₃ pyrazin-2-ylmethyl 5 ', 2' ch ₃ 785 ch ₃ pyrimidin-2-ylmethyl ^C 2 ^H 5 ch ₃ 786 ch ₃ fur-2-ylmethyl ^C 2 ^H 5 ch ₃ 787 ch ₃ pyrro1-2-ylmethy1 ^C 2 ^H 5 ch ₃ 788 ch ₃ N-methylpyrrole-2-ylmethyl ^C 2 ^H 5 ch ₃ 789 ch ₃ thien-2-ylmethyl ^C 2 ^H 5 ch ₃ 790 ch ₃ isoxazol-5-ylmethyl ^C 2 ^H 5 ch ₃ 791 ch ₃ thiazol-2-ylmethyl 5 ', 2' ch ₃ 792 ch ₃ thiazol-5-ylmethyl ^C 2 ^H 5 ch ₃ 793 ch ₃ oxazol-2-ylmethyl ^C 2 ^H 5 ch ₃ 794 ch ₃ pyrazol-3-ylmethyl ^C 2 ^H 5 ch ₃ 795 ch ₃ benzofuran-2-ylmethyl ^C 2 ^H 5 ch ₃ 796 ch ₃ indol-2-ylmethyl ^C 2 ^H 5 ch ₃ 797 ch ₃ indol-3-ylmethyl ^C 2 ^H 5 ch ₃ 798 ch ₃ benzothiazol-2-ylmethyl ^C 2 ^H 5 ch ₃ 799 ch ₃ quinolin-2-ylmethyl ^C 2 ^H 5 ch ₃ 800 ch ₃ 4-Cl-C ₆ H ₄ OCH (CH ₃₎ CH ₂ ^C 2 ^H 5 , ch ₃

124

Table 7

R ^2x S

R ⁶

O-C-N (CH3) 2

Merge · ”number R ¹ R ² R ¹ 1 H H H 2 H ch ₃ H 3 H tert. 'C ₄ H _g H 4 H ch ₂ = ch-ch ₂ H 5 H ch ₂ = c (cl) -ch ₂ H 6 H CH ₂ = C (CH ₃ ) -CH ₂ H 7 H ch ₃ ch = ch-ch ₂ H 8 H hc = cch ₂ H 9 H CH ₃ CsC-CH ₂ H 10 H cycloalkyl CGH-Lj H 11 H ^C 6 ^H 5 ^CH 2 H 12 H 2-FC ₆ H ₄ -CH ₂ H 13 H 3-FC ₆ H ₄ -CH ₂ H 14 H 4-FC ₆ H ₄ -CH ₂ H 15 H 2-Cl-C ₆ H ₄ CH ₂ H 16 H 3-Cl-C ₆ H ₄ CH ₂ H 17 H 4-Cl-C ₆ H ₄ CH ₂ H 18 H 2-Br-C ₆ H ₄ CH ₂ H 19 H 3-Br-C ₆ H ₄ CH ₂ H 20 H 4-Br-C ₆ H ₄ CH ₂ H 21 H 2-CH ₃ -C ₆ H ₄ -CH ₂ H 22 H 3-CH ₃ -C ₆ H ₄ -CH ₂ H 23 H 4-CH ₃ -C ₆ ^H ₄ -CH ₂ H 24 H 2-CF ₃ - ^C 6 H ₄ -C 2 ^H H

125

table 7 - continued Bile. number R ¹ R ² R

25 H 3-CF ₃ ^-C 6 ^H ₄ ^-CH 2 H 26 4-CF ₃ -C ₆ H ₄ -CH ₂ H 27 H 2-ISO-C ₃ H ₇ -C ₆ H ₄ -CH ₂ H 28 H 3-ISO-C ₃ H ₇ -C ₈ H ₄ -CH ₂ H 29 H 4-iso-C ₃ H ₇ -C ₈ H ₄ -CH ₂ H 30 H 2-tert-C ₄ H ₉ -C ₆ H ₄ -CH ₂ H 31 H 3-t-C ₄ H _{g 4 -CH2} -CgH H 32 H 4-tert-C ₄ H ₉ -C ₈ H ₄ -CH ₂ H 33 H 2-CH ₃ O-C ₈ H ₄ -CH ₂ H 34 H 3-CH ₃ O-C ₈ H ₄ -CH ₂ H 35 H ' 4-CH ₃ OC ₆ H ₄ -CH ₂ H 36 H 2-cyano-C ₆ H ₄ CH ₂ H 37 H _{3-cyano-4-CH 2} CGH H 38 H _{4-cyano-4-CGH CH2} H 39 H _{2-nitro-4-CH 2} CGH H 40 H _{3-nitro-4-CH 2} CGH H 41 H _{4-nitro-4-CH 2} CGH H 42 H 2 _of 4-Cl ₂ -C ₈ H ₃ -CH ₂ H 43 H 3,4-Cl ₂ -C ₈ H ₃ -CH ₂ H 44 H 3,5-Cl ₂ -C 8 ^H 3 ^-CH 2 H 45 H 2,6-Cl ₂ -C ₈ H ₃ -CH ₂ H 46 H 2M- (CH ₃ ) ₂ -C ₈ H ₃ -CH ₂ H 47 H 2,5- (CH ₃ ) ₂ -C ₈ H ₃ -CH ₂ H 48 H 3,4- (CH ₃ ) ₂ -C ₈ H ₃ -CH ₂ H 49 H 3,5- (CH ₃ ) ₂ -C ₈ H ₃ -CH ₂ H 50 H _{l-naphthyl-CH2} H 51 H _{2-naphthyl-CH2} H 52 H C ₆ H ₅ -CH (CH ₃ ) H 53 _t H 2-Cl-CGH ₄ -CH (CH ₃₎ H 54 H 3-Cl-CGH ₄ -CH (CH ₃₎ H

126

Table 7 - continued

Bile.

number R ¹ R ² R ' 55 H 4-Cl-C ₆ H ₄ -CH (CH ₃ ) H 56 F 2-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) H 57 H 3-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) H 58 H 4-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) H 59 H 2-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) H 60 H 3-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) H 61 H 4-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) H 62 H 2-tert-C ₄ H ₉ -C ₆ H ₄ -CH (CH ₃ ) H 63 H 3-tert-C ₄ H _g -C ₆ H ₄ -CH (CH ₃ ) H 64 H 4-tert-C ₄ H ₉ -C ₆ H ₄ -CH (CH ₃ ) H 65 H C 2-CH ₃ OC ₆ H ₄ -CH (CH ₃ ) H 66 H 3-CH ₃ OC ₆ H ₄ -CH (CH ₃ ) H 67 H 4-CH ₃ OC ₆ H ₄ -CH (CH ₃ ) H 68 H 2-cyano-C ₆ H ₄ -CH (CH ₃₎ H 69 H 3-cyano-C ₆ H ₄ -CH (CH ₃₎ H 70 H 4-cyano-C ₆ H ₄ -CH (CH ₃₎ H 71 H 2,4-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) H 72 H 3,4-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) H 73 H 3,5-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) H 74 H 2,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH (CH ₃ ) H 75 H 2,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH (CH ₃ ) H 76 H ch ₃ ooc-ch ₂ H 77 H c ₂ h ₅ ooc-ch ₂ H 78 H IZO-C ₃ H ₇ 00C-CH ₂ H 79 H tert-C ₄ H ₉ OOC-CH ₂ H 80 H tert-C ₄ H ₉ OOC-CH (CH ₃ ) H 81 H n = c-ch ₂ H 82 H c ₆ h ₅ co-ch ₂ H 83 H pyridin-2-ylmethyl H 84 H pyrazin-2-ylmethyl H

127

Table 7 - continued

Bile.

number R ¹ R ² R ¹ 85 H pyrimidin-2-ylmethyl H 86 H fur-2-ylmethyl H 87 H pyrrol-2-ylmethyl H 88 H N-methylpyrrole-2-ylmethyl H 89 H thien-2-ylmethyl H 90 H isoxazol-5-ylmethyl H 91 H thiazol-2-ylmethyl H 92 H thiazol-5-ylmethyl H 93 H oxazol-2-ylmethyl H ⁹⁴ H pyrazol-3-ylmethyl H 95 '· H benzofuran-2-ylmethyl H 96 H indol-2-ylmethyl H 97 H indol-3-ylmethyl H 98 H benzothiazol-2-ylmethyl H 99 H quinolin-2-ylmethyl H 100 H 4-c1-c ₆ h ₄ and (ch ₃ ) -ch ₂ H 101 ch ₃ H H 102 ^CH 3 ch ₃ H 103 ch ₃ t-C ₄ H _g H 104 ch ₃ ch ₂ = ch-ch ₂ H 105 ch ₃ CH ₂ = C (C1) -CH ₂ H 106 ch ₃ CH ₂ = C (CH ₃ ) -CH ₂ H 107 ch ₃ ch ₃ ch = ch-ch ₂ H 108 ch ₃ hc = cch ₂ H 109 ch ₃ CH ₃ CsC-CH ₂ H 110 ch ₃ cyclo-C 9 H ₁₁ H 111 ch ₃ ^C 6 ^H 5 ^CH 2 H 112 ch ₃ 2-FC ₆ H ₄ -CH ₂ H 113 ch ₃ 3-FC ₆ H ₄ -CH ₂ H 114 ch ₃ 4-F- ^c 6 ^h 4 ^-CH 2 H

128

Table 7 - continued

Bile.

number R ¹ R ² R ' 115 ch ₃ 2-Cl-C ₆ H ₄ CH ₂ H 116 ch ₃ 3-Cl-C ₆ H ₄ CH ₂ H 117 ch ₃ 4-Cl-C ₆ H ₄ CH ₂ H 118 ch ₃ 2-Br-C ₆ H ₄ CH ₂ H 119 ch ₃ 3-Br-C ₆ H ₄ CH ₂ H 120 ch ₃ 4-Br-C ₆ H ₄ CH ₂ H 121 ch ₃ 2-CH ₃ -C ₆ H ₄ -CH ₂ H 122 ch ₃ 3-CH ₃ -C ₆ H ₄ -CH ₂ H 123 ch ₃ 4-CH ₃ -C ₆ H ₄ -CH ₂ H 124 ch _{3 2} -CF ₃ ^-C 6 ^H 4 ^-CH 2 H 125 ch ₃ 3-CF ₃ ^-C 6 ^H 4 ^CH 2 H 126 ch ₃ ⁴ - ^CF 3 - ^C 6 ^H 4 ^CH 2 H 127 ch ₃ 2-iso-C ₃ H ₇ -C ₆ H ₄ -CH ₂ H 128 ch ₃ 3-ZOOC ₃ H ₇ -C ₆ H ₄ -CH ₂ H 129 ch ₃ 4-iso-C ₃ H ₇ -C ₈ H ₄ -CH ₂ H 130 ch ₃ 2-tert-C ₄ H ₉ -C ₆ H ₄ -CH ₂ H 131 ch ₃ 3-tert-C ₄ H 8 -C 8 H ₄ -CH ₂ H 132 ch ₃ 4-tert-C ₄ H ₉ -C ₆ H ₄ -CH ₂ H 13 3 ch ₃ 2-CH ₃ OC ₆ H ₄ -CH ₂ H 134 ch ₃ 3-CH ₃ OC ₆ H ₄ -CH ₂ H 135 ch ₃ 4-CH ₃ OC ₆ H ₄ -CH ₂ H 136 ch ₃ 2-cyano- C ₆ H ₄ -CH ₂ H 137 ch ₃ 3-cyano-C ₆ H ₄ CH ₂ H 138 ch _{3 4-cyano-4-CH 2} CGH H 139 ch _{3 2-nitro-4-CH 2} CGH H 140 ch ₃ 3-nitro-C ₆ H ₄ CH ₂ H 141 ch _{3 4-nitro-4-CGH CH2} H 142 ch ₃ 2,4-Cl ₂ -C ₆ ^H 3 ^-c H 2 H 143 ch ₃ 3,4-Cl ₂ -C ₆ H ₃ -CH ₂ H 144 ch ₃ 3,5-Cl ₂ -C ₈ H ₃ -CH ₂ H

129

Table 7 - continued

Bile.

number R ¹ R ² R ' 145 ch ₃ 2,6-Cl ₂ -C ₆ H ₃ -CH ₂ H 146 ch ₃ 2,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ H 147 ch ₃ 2,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ H 148 ch ₃ 3,4- (CH ₃ ) 2 -C ₆ H ₃ -CH ₂ H 149 ch ₃ 3,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ H 150 ch _{3 l-naphthyl-CH2} H 151 ch _{3 2-naphthyl-CH2} H 152 ch ₃ c ₆ h ₅ -ch (ch ₃ ) H 153 ch ₃ 2-Cl-C ₆ H ₄ -CH (CH ₃₎ H 154 ch ₃ 3-Cl-C ₆ H ₄ -CH (CH ₃₎ H 155 ch ₃ 4-Cl-C ₆ H ₄ -CH (CH ₃ ) H 156 ch ₃ 2-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) H 157 ch ₃ 3-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) H 158 ch ₃ 4-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) H 159 ch ₃ 2-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) H 160 ch ₃ 3-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) H 161 ch ₃ 4-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) H 162 ch ₃ 2-tert-C ₄ H _g -C ₆ H ₄ -CH (CH ₃ ) H 163 ch ₃ 3-tert-C ₄ H _g -C ₆ H ₄ -CH (CH ₃ ) H 164 ch ₃ 4-tert-C ₄ H ₉ -C ₆ H ₄ -CH (CH ₃ ) H 165 ch ₃ 2-CH ₃ OC ₆ H ₄ -CH (CH ₃ ) H 166 ch ₃ 3-CH ₃ O-C ₈ H ₄ -CH (CH ₃ ) H 167 ch ₃ 4-CH ₃ O-C ₈ H ₄ -CH (CH ₃ ) H 168 ch ₃ 2-cyano-CGH ₄ -CH (CH ₃₎ H 169 ch ₃ 3-cyano-CGH ₄ -CH (CH ₃₎ H 170 ch ₃ 4-cyano-C ₆ H ₄ -CH (CH ₃₎ H 171 ch ₃ 2,4-Cl ₂ -C ₈ H ₃ -CH (CH ₃ ) H 172 ch ₃ 3,4-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) H 173 ch ₃ 3,5-Cl ₂ -C ₈ H ₃ -CH (CH ₃ ) H 174 ch ₃ 2,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH (CH ₃ ) H

130

Table 7 - continued

Bile.

number R ¹ R ² R ⁶ 175 ch ₃ 2,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH (CH ₃ ) H 176 ch ₃ ch ₃ ooc-ch ₂ H 177 ch ₃ c ₂ h ₅ ooc-ch ₂ H 178 ch ₃ i: oC ₃ H ₇ OOC-CH ₂ H 179 ch ₃ tert-C ₄ H ₉ OOC-CH ₂ H 180 ch ₃ tert-C ₄ H ₉ OOC-CH (CH ₃ ) H 181 ch ₃ n = c-ch ₂ H 182 ch ₃ ^C 6 ^H 5 ^C ° ^-CH 2 H 183 ch ₃ pyridin-2-ylmethyl H 184 ch ₃ pyrrolidine-2-ylmethyl H 185 ch ₃ pyrimidin-2-ylmethyl H 186 ch ₃ fur-2-ylmethyl H 187 ch ₃ pyrrol-2-ylmethyl H 188 ch ₃ N-methylpyrrole-2-ylmethy1 H 189 ch ₃ thien-2-ylmethyl H 190 ch ₃ isoxazol-5-ylmethyl H 191 ch ₃ thiazol-2-ylmethyl H 192 ch ₃ thiazol-5-ylmethyl H 193 ch ₃ oxazol-2-ylmethyl H 194 ch ₃ pyrazol-3-ylmethyl H 195 ch ₃ benzofuran-2-ylmethyl H 196 ch ₃ indol-2-ylmethyl H 197 ch ₃ indol-3-ylmethyl H 198 ch ₃ benzothiazol-2-ylmethyl H 199 ch ₃ quinolin-2-ylmethyl H 200 ch ₃ 4-ci-c ₆ h ₄ and (ch ₃ ) -ch ₂ H 201 H H ch ₃ 202 H ch ₃ ch ₃ 203 H t-c ₄ H _g ch ₃ 204 H ch ₂ = ch-ch ₂ ch ₃

131

Table 7 - continued

Bile.

number R ¹ R ² R ⁶ 205 H CH ₂ = C (C1) -CH ₂ ch ₃ 206 H ch ₂ = c (ch ₃ ) -ch ₂ ch ₃ 207 H ch ₃ ch = ch-ch ₂ ch ₃ 208 H hc = cch ₂ ch ₃ 209 H ch ₃ c = c-ch ₂ ch ₃ 210 H CGH-cycloalkyl-Q ch ₃ 211 H ^C 6 ^H 5 ^CH 2 ch ₃ 212 H 2-FC ₆ H ₄ -CH ₂ ch ₃ 213 H 3-FC ₆ H ₄ -CH ₂ ch ₃ 214 H 4-F- ^C 6 ^H 4 ^-CH 2 ch ₃ 215 H 2-Cl-C ₆ H ₄ CH ₂ ch ₃ 216 H 3-C 1-C ₆ H ₄ CH ₂ ch ₃ 217 H 4-Cl-C ₆ H ₄ CH ₂ ch ₃ 218 H 2-Br-C ₆ H ₄ CH ₂ ch ₃ 219 H 3-Br-C ₆ H ₄ CH ₂ ch ₃ 220 H 4-Br-C ₆ H ₄ CH ₂ ch ₃ 221 H 2-CH ₃ -C ₆ H ₄ -CH ₂ ch ₃ 222 H 3-CH ₃ -C ₆ H ₄ -CH ₂ ch ₃ 223 H 4-CH ₃ -C ₆ H ₄ -CH ₂ ch ₃ 224 H 2-CF ₃ -C ₆ H ₄ -CH ₂ ch ₃ 225. H 3-CF ₃ -C ₆ H ₄ -CH ₂ ch ₃ 226: H 4-CF ₃ -C ₆ H ₄ ^-CH 2 ch ₃ 227 H 2J 12J o ^- -CH 2 ch ₃ 228 H 3-ISO-C ₃ H ₇ -C ₈ H ₄ -CH ₂ ch ₃ 229 H 4 "1Ζθ" ΌβΗ · 7 "Ο ^ Η ^" ΟΗ2 ch ₃ 230 H 2-tert-C ₄ H ₉ -C ₆ H ₄ -CH ₂ ch ₃ 231 H 3-tert-C ₄ H ₉ -C ₈ H ₄ -CH ₂ ch ₃ 232 H 4-tert-C ₄ H ₉ -C ₆ H ₄ -CH ₂ ch ₃ 233 H 2-CH ₃ O-C ₈ H ₄ -CH ₂ ch ₃ 234 H 3-CH ₃ OC ₆ H ₄ -CH ₂ ch ₃

132

Table 7 - continued

Bile.

number R ¹ R ² R ⁶ 235 H 4-CH ₃ OC ₆ H ₄ -CH ₂ ch ₃ 236 H _{2-cyano-4-CH 2} CGH ch ₃ 237 H 3-cyano-C ₆ H ₄ CH ₂ ch ₃ 238 H _{4-cyano-4-CH 2} CGH ch ₃ 239 H 2-nitro-C ₆ H ₄ CH ₂ ch ₃ 240 H: _{3-nitro-4-CH 2} CGH ch ₃ 241 H _{4-nitro-4-CH 2} CGH ch ₃ 242 H 2,4-Cl ₂ -C ₆ H ₃ -CH ₂ ch ₃ 243 H 3,4-Cl ₂ -C ₆ ^h ₃ ^-CH 2 ch ₃ 244 H 3,5-Cl ₂ -C ₆ H ₃ -CH ₂ ch ₃ 245 H 2,6-Cl ₂ -C ₆ H ₃ -CH ₂ ch ₃ 246 H 2,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ ch ₃ 247 H 2,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ ch ₃ 248 H 3,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ ^CH 3 249 H 3,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ ch ₃ 250 H _{l-naphthyl-CH2} ch ₃ 251 H _{2-naphthyl-CH2} ch ₃ 252 H c ₆ h ₅ -ch (ch ₃ ) ch ₃ 253 H 2-Cl-C ₆ H ₄ -CH (CH ₃₎ ch ₃ 254 H 3-Cl-C ₆ H ₄ -CH (CH ₃₎ ch ₃ 255 H 4-Cl-C ₆ H ₄ -CH (CH ₃ ) ch ₃ 256 H 2-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) ch ₃ 257 H 3-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) ^CH 3 258 H 4-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) ch ₃ 259 H 2-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) ch ₃ 260 H 3-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) ch ₃ 261 H 4-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) ch ₃ 262 H 2-tert-C ₄ H ₉ -C ₆ H ₄ -CH (CH ₃ ) ch ₃ 263 H 3-tert-C ₄ H ₉ -C ₆ H ₄ -CH (CH ₃ ) ch ₃ 264 H 4-tert-C ₄ H ₉ -C ₆ H ₄ -CH (CH ₃ ) ch ₃

133

Table 7 - continued

Bile.

number R ¹ R ² R ⁶ 265 H 2-CH ₃ OC ₆ H ₄ -CH (CH ₃ ) ch ₃ 266 H 3-CH ₃ OC ₆ H ₄ -CH (CH ₃ ) ch ₃ 267 H 4-CH ₃ OC ₆ H ₄ -CH (CH ₃ ) ch ₃ 268 H 2-cyano-C ₆ H ₄ -CH (CH ₃₎ ch ₃ 269 H 3-cyano-C ₆ H ₄ -CH (CH ₃₎ ch ₃ 270 H 4-cyano-C ₆ H ₄ -CH (CH ₃₎ ch ₃ 271 H 2,4-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) ch ₃ 272 H 3,4-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) ch ₃ 273 H 3,5-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) ch ₃ 274 H 2,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH (CH ₃ ) ch ₃ 275 H 2,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH (CH ₃ ) ch ₃ 276 H ch ₃ ooc-ch ₂ ch ₃ 277 H c ₂ h ₅ ooc-ch ₂ ch ₃ 278 H IZO-C ₃ H ₇ 00C-CH ₂ ch ₃ 279 H t-C ₄ H ₈ OOC-CH ₂ ch ₃ 280 H tert-C ₄ H ₉ OOC-CH (CH ₃ ) ch ₃ 281 H _NSC-CH2 ch ₃ 282 H C ₆ ^H 5 ^C ° ^-CH 2 ch ₃ 283 H pyridin-2-ylmethyl ch ₃ 284 H pyrazin-2-ylmethyl ch ₃ 285 H pyrimidin-2-ylmethyl ch ₃ 286 H fur-2-ylmethyl ch ₃ 287 H pyrrol-2-ylmethyl ch ₃ 288 H N-methylpyrrole-2-ylmethyl ch ₃ 289 H thien-2-ylmethyl ch ₃ 290 H isoxazol-5-ylmethyl ch ₃ 291 H thiazol-2-ylmethyl ch ₃ 292 H thiazol-5-ylmethyl ch ₃ 293 H oxazol-2-ylmethyl ch ₃ 294 H pyrazol-3-ylmethyl ch ₃

134

Table 7 - continued

Bile.

number R ¹ R ² R ⁶ 295 H benzofuran-2-ylmethyl ch ₃ 296 H indol-2-ylmethyl ch ₃ 297 H indol-3-ylmethyl ch ₃ 298 H benzothiazol-2-ylmethyl ch ₃ 299 H quinolin-2-ylmethyl ch ₃ 300 H 4-ci-c ₆ h ₄ and (ch ₃ ) -ch ₂ ch ₃ 301 ch ₃ H ch ₃ 302 ch ₃ ch ₃ ch ₃ 303 ch ₃ t-C ₄ H ₉ ch ₃ 304 ch ₃ ch ₂ = ch-ch ₂ ch ₃ 305 ch ₃ CH ₂ = C (C1) -CH ₂ ch ₃ 306 ch ₃ CH ₂ = C (CH ₃ ) -CH ₂ ch ₃ 307 ch ₃ ch ₃ ch = ch-ch ₂ ch ₃ 308 ch ₃ hc = cch ₂ ch ₃ 309 ch ₃ CH ₃ CsC-CH ₂ ch ₃ 310 ch ₃ cycloalkyl CGH ^ ch ₃ 311 ch ₃ C ₆ H ₅ - ^CH 2 ch ₃ 312 ch ₃ 2-FC ₆ H ₄ -CH ₂ ch ₃ 313 ch ₃ 3-FC ₆ H ₄ -CH ₂ ch ₃ 314 ch ₃ 4-FC ₆ H ₄ -CH ₂ ch ₃ 315 ch ₃ 2-Cl-C ₆ H ₄ CH ₂ ch ₃ 316 ch ₃ 3-Cl-C ₆ H ₄ CH ₂ ch ₃ 317 ch ₃ 4-Cl-C ₆ H ₄ CH ₂ ch ₃ 318 ch ₃ 2-Br-C ₆ H ₄ CH ₂ ch ₃ 319 ch ₃ 3-Br-C ₆ H ₄ CH ₂ ch ₃ 320 ch ₃ 4-Br-C ₆ H ₄ CH ₂ ch ₃ 321 ch ₃ 2-CH ₃ -C ₆ H ₄ -CH ₂ ch ₃ 322 ch ₃ 3-CH ₃ -C ₆ H ₄ -CH ₂ ch ₃ 323 ch ₃ 4-CH ₃ - ^c 6 ^H 4 ^-ch 2 ch ₃ 324 ch ₃ 2-CF ₃ -C ₆ H ₄ -CH ₂ ch ₃

135

Table 7 - continued

Bile.

number R ¹ R ² R ⁶ 325 ch ₃ 3-CF ₃ -C ₆ H ₄ -CH ₂ ch ₃ 326 ch ₃ 4-CF ₃ -C ₆ H ₄ -CH ₂ ch ₃ 327 ch ₃ 2-iso-C ₃ H ₇ -C ₆ H ₄ -CH ₂ ch ₃ 328 ch ₃ 3-iso-C ₃ H ₇ -C ₆ H ₄ -CH ₂ ch ₃ 329 ch ₃ 4-iso-C ₃ H ₇ -C ₈ H ₄ -CH ₂ ch ₃ 330 ch ₃ 2-tert-C ₄ H ₉ -C ₆ H ₄ -CH ₂ ch ₃ 331 ch ₃ 3-tert-C ₄ H ₉ -C ₆ H ₄ -CH ₂ ch ₃ 332 ch ₃ 4-tert-C ₄ H ₉ -C ₆ H ₄ -CH ₂ ch ₃ 333 ch ₃ 2-CH ₃ O-C ₈ H ₄ -CH ₂ ch ₃ 334 ch ₃ 3-CH ₃ OC ₆ H ₄ -CH ₂ ch ₃ 335 ch ₃ 4-CH ₃ O-C ₆ H ₄ -CH ₂ ch ₃ 336 ch _{3 2-cyano-4-CH 2} CGH ch ₃ 337 ch ₃ 3-cyano-C ₆ H ₄ CH ₂ ch ₃ 338 ch ₃ 4-cyano-C ₆ H ₄ CH ₂ ch ₃ 339 ch _{3 2-nitro-4-CGH CH2} ch ₃ 340 ch ₃ 3-nitro-C ₆ H ₄ CH ₂ ch ₃ 341 ch ₃ 4-nitro-C ₆ H ₄ CH ₂ ch ₃ 342 ch ₃ 2,4-Cl ₂ -C ₆ H ₃ -CH ₂ ch ₃ 343 ch ₃ 3,4-Cl ₂ -C ₆ H ₃ - ^c H ₂ ch ₃ 344 ch ₃ 3,5-Cl ₂ -C ₆ H ₃ -CH ₂ ch ₃ 345 ch ₃ 2,6-Cl ₂ -C ₆ H ₃ -CH ₂ ch ₃ 346 ch ₃ 2,4- (CH ₃ ) ₂ ^-C 6 ^H 3 ^-CH 2 ch ₃ 347 ch ₃ 2 / 5- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ ch ₃ 348 ch ₃ 3,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ ch ₃ 349 ch ₃ 3,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ ch ₃ 350 ch _{3 l-naphthyl-CH2} ch ₃ 351 ch _{3 2-naphthyl-CH2} ch ₃ 352 ch ₃ c ₆ h ₅ -ch (ch ₃ ) ch ₃ 353 ch ₃ 2-Cl-C ₆ H ₄ -CH (CH ₃₎ ch ₃ 354 ch ₃ 3-Cl-C ₆ H ₄ -CH (CH ₃₎ ch ₃

136

Table 7 - continued

Bile.

number R ¹ R ² R ⁶ 355 ch ₃ 4-Cl-C ₆ H ₄ -CH (CH ₃ ) ch ₃ 356 ch ₃ 2-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) ch ₃ 357 ch ₃ 3-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) ch ₃ 358 ch ₃ 4-CH ₃ -C ₆ H ₄ -CH (CH ₃ ) ch ₃ 359 ch ₃ 2-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) ch ₃ 360 ch ₃ 3-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) ch ₃ 361 ch ₃ 4-CF ₃ -C ₆ H ₄ -CH (CH ₃ ) ch ₃ 362 ch ₃ 2-tert-C ₄ H ₉ -C ₆ H ₄ -CH (CH ₃ ) ch ₃ 363 ch ₃ 3-tert-C ₄ H ₉ -C ₆ H ₄ -CH (CH ₃ ) ch ₃ 364 ch ₃ 4-tert-C ₄ H ₉ -C ₆ H ₄ -CH (CH ₃ ) ch ₃ 365 ch ₃ 2-CH ₃ OC ₆ H ₄ -CH (CH ₃ ) ch ₃ 366 ch ₃ 3-CH ₃ OC ₆ H ₄ -CH (CH ₃ ) ^CH 3 367 ch ₃ 4-CH ₃ OC ₆ H ₄ -CH (CH ₃ ) ch ₃ 368 ch ₃ 2-cyano-C ₆ H ₄ -CH (CH ₃₎ ch ₃ 369 ch ₃ 3-cyano-CGH ₄ -CH (CH ₃₎ ch ₃ 370 ch ₃ 4-cyano-C ₆ H ₄ -CH (CH ₃₎ ch ₃ 371 ch ₃ 2,4-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) ch ₃ 372 ch ₃ 3,4-Cl ₂ -C ₆ H ₃ -CH (CH ₃ ) ch ₃ 373 ch ₃ 3,5-Cl ₂ -C ₈ H ₃ -CH (CH ₃ ) ch ₃ 374 ch ₃ 2,4- (CH ₃ ) ₂ -C ₈ H ₃ -CH (CH ₃ ) ch ₃ 375 ch ₃ 2,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH (CH ₃ ) ch ₃ 376 ch ₃ ch ₃ ooc-ch ₂ ch ₃ 377 ch ₃ c ₂ h ₅ ooc-ch ₂ ch ₃ 378 ch ₃ o-c ₃ h ₇ ooc-ch ₂ ch ₃ 379 ch ₃ tert-C ₄ H ₉ OOC-CH ₂ ch ₃ 380 ch ₃ tert-C ₄ H _g OOC-CH (CH ₃ ) ch ₃ 381 ch _{3 NSC-CH2} ch ₃ 382 ch ₃ C ₆ H ₅ CO-CH ₂ ch ₃ 383 ch ₃ pyridin-2-ylmethyl ch ₃ 384 ch ₃ pyrrolidine-2-ylmethyl ch ₃

137

table 7 - continued Key, number R ¹ R ² R ⁶

385 ch ₃ pyrimidin-2-ylmethyl ch ₃ 386 ch ₃ fur-2-ylmethyl ch ₃ 387 ch ₃ pyrrol-2-ylmethyl ch ₃ 388 ch ₃ N-methylpyrrole-2-ylmethyl ch ₃ 389 ch ₃ thien-2-ylmethyl ch ₃ 390 ch ₃ isoxazol-5-ylmethyl ch ₃ 391 ch ₃ thiazol-2-ylmethyl ch ₃ 392 ch ₃ thiazol-5-ylmethyl ch ₃ 393 ch ₃ oxazol-2-ylmethyl ch ₃ 394 ch ₃ pyrazol-3-ylmethyl ch ₃ 395 ch ₃ benzofuran-2-ylmethyl ch ₃ 396 ch ₃ indol-2-ylmethyl ch ₃ 397 ch ₃ indol-3-ylmethyl ch ₃ 398 ch ₃ benzothiazol-2-ylmethyl ch ₃ 399 ch ₃ quinolin-2-ylmethyl ch ₃ 400 ch ₃ 4-ci-c ₆ h ₄ and (ch ₃ ) -ch ₂ ch ₃

138

usefulness

The novel compounds of formula I are useful as fungicidal agents.

The novel compounds or compositions containing such compounds can be used, for example, in the form of directly sprayable solutions, powders, suspensions, also high-percentage aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, scatters or granules by spraying, fogging, dusting, sprinkling or sprinkling. The dosage forms depend on the intended use, and in any case are intended to ensure the finest possible distribution of the active ingredient according to the invention.

Generally, the plants are sprayed or dusted with the active substances or treated with the seeds of the plants.

The compositions are prepared in a manner known per se, for example by adjusting the active ingredient with solvents and / or carriers, optionally using an emulsifying agent and a dispersing agent, where other organic solvent adjuvants, such as solvents such as auxiliary solvents, may also be used in the case of water. . Essentially, aromatic compounds (e.g. xylene), chlorinated flavors (e.g. chlorobenzene), paraffinic compounds (e.g. fraction from petroleum distillation), alcohols (e.g. methanol or butanol), ketones (e.g. cyclohexanone), amines (e.g. ethanolamine or dimethylformamide) and water, kaolins, clays, talc (for example, high natural stone meal (e.g. or chalk) and synthetic stone meal disperse silicic acid or silicates), emulsifying agents such as non-ionic or anionic emulsifiers (e.g. polyoxyethylene ethers of aliphatic alcohols, alkylsulfonates and arylsulfonates) and dispersing agents such as lignin from sulfite waste liquors and methylcellulose.

139

Suitable surfactants are the alkali metal salts, alkali metal salts and ammonium salts of aromatic sulfonic acids, such as salts of ligninsulfonic acid, phenolsulfonic acid, naphthalenesulfonic acid and dibutylnaphthalenesulfonic acid, as well as fatty acids, alkylsulfonates and alkyl aryl sulfates. alcohols, as well as salts of sulfated hexadecanols, heptanecanols and octadecanols, as well as glycol ethers of aliphatic alcohols, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene phenol, phenol ethylene phenol, phenoxyethylene phenol tributylphenyl glycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, condensation products of ethylene oxide with aliphatic alcohols, ethoxylated castor oil, polyoxyethylene alkyl ether or polyoxypropylene, lauryl alcohol polyglycol ether acetate, sorbitester, sulphite lignin lignin or methylcellulose.

Powder, grit and dust compositions can be made by mixing or grinding the active ingredients with a solid carrier.

Granules, for example coated, impregnated and homogeneous granules, can be prepared by applying the active ingredient to a solid carrier. Solid carriers are mineral clays such as silica gel, silica, diatomaceous earth, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium sulphate, magnesium sulphate, magnesium oxide, ground plastic materials, fertilizers such as ammonium sulphate, ammonium nitrate, ammonium phosphate, ureas and plant products such as cereal flour, tree bark flour, wood and nutshell flour, cellulose powder and other solid carriers.

140

Examples of such means are:

I. 90 parts by weight of Compound No. 2 of Table 1 (i.e., Compound No. 2/1) is mixed with 10 parts by weight of N-methyl-α-pyrrolidone to form a solution suitable for use as minimal drops.

II. 20 parts by weight of compound No. 36 of Table 1 (hereinafter referred to as compound number 1/36) is dissolved in a mixture consisting of 80 parts by weight of xylene, 10 parts by weight of adduct of 8 to 10 moles of ethylene oxide and 1 mol of N-monoethanolamide oleic acid. 5 parts by weight of the calcium salt of dodecylbenzenesulfonic acid and 5 parts by weight of the addition product of 40 moles of ethylene oxide and 1 mol of castor oil. Pouring this solution into water and finely distributing it gives an aqueous dispersion.

III. 20 parts by weight of compound No. 1/49 are dissolved in a mixture consisting of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol and 20 parts by weight of an adduct of 40 moles of ethylene oxide and 1 mol of castor oil. Pouring this solution into water and finely distributing it gives an aqueous dispersion.

IV. 20 parts by weight of compound No 1/58 are dissolved in a mixture consisting of 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction at a boiling point of 210 to 280 ° C and 10 parts by weight of an adduct of 40 moles of ethylene oxide and 1 mol of castor oil. Pouring this solution into water and finely distributing it gives an aqueous dispersion.

V. 80 parts by weight of Compound No. 1/2 are well mixed with 3 parts by weight of diisobutylnaphthalene-α-sulfonic acid sodium salt, 10 parts by weight of lignin sulphonic acid sodium salt from sulphite waste liquors and 7 parts by weight of powdered silica gel, and

141 the resulting mixture was ground in a hammer mill. Gently dispersing this mixture in water gives a spray suspension.

VI. 3 parts by weight of compound No. 1/36 are mixed intimately with 97 parts by weight of finely dispersed kaolin. In this way, a dust containing 3% by weight of the active ingredient is obtained.

VII. 30 parts by weight of compound No. 1/49 is mixed intimately with a mixture of 92 parts by weight of powdered silica gel and 8 parts by weight of paraffinic oil which has been sprayed onto the surface of this silica gel. In this way, an effective composition with good adhesion is obtained.

VIII. 40 parts by weight of compound No. 1/58 are thoroughly mixed with 10 parts by weight of sodium condensation product of phenolsulfonic acid, urea and formaldehyde, 2 parts by weight of silica gel and 48 parts by weight of water. A stable aqueous dispersion is obtained which can be further diluted with water to form an aqueous dispersion.

IX. 20 parts by weight of Compound No. 1/2 are intimately mixed with 2 parts by weight of dodecylbenzenesulfonic acid calcium salt, 8 parts by weight of aliphatic alcohol polyglycol ether, 20 parts by weight of phenolsulfonic acid condensation product, urea and formaldehyde, and 68 parts by weight of paraffinic mineral oil. A stable oil dispersion is obtained.

The novel compounds exhibit excellent activity against a wide range of plant pathogenic fungi, in particular from the Ascomyceten and Basidiomyceten classes. These compounds are in part systemically active and can be used as foliar and soil fungicidal agents.

The compounds are of particular importance for controlling a variety of fungi on various crop plants such as wheat, rye, barley,

142 oats, rice, corn, grass, cotton, soybeans, coffee, sugar cane, grapevine, fruit trees and ornamental plants, as well as vegetables such as cucumbers, beans and pumpkin plants, as well as on the seeds of these plants.

The compounds are useful when the seed, plants, materials or soil to be protected from fungi or fungal infestations are treated with a fungicidally effective amount of the active compounds.

The use takes place before or after infection of the materials, plants or seeds by the fungi.

The compounds are particularly useful for controlling the following plant diseases:

Erysiphe graminis for grain,

Erysiphe cichoracearum and Sphaerotheca fuliginea on pumpkin plants,

Podosphaera leucotricha on apple trees,

Unicinula necator on grapevines, Pucinia grains, Rhizoctonia on cotton and turf grass, Ustilago grains and sugar cane,

Venturia inaequalis on apple trees, Helminthosporia species for grain,

Septoria nodorum on wheat,

Botrytis cinerea on strawberries and grapevines,

Cercospora arachidicola on peanuts,

Pseudocercosporella herpotrichoides on wheat and barley, Pyricularia oryzae on rice,

Phytophthora infestans on potatoes and tomatoes, Fusaria and Verticillia species on various plants, Plasmopara viticola on vines and Alternaria species on vegetables and fruits.

The novel compounds can also be used to protect materials (wood protection), for example against Paecilomyces variotii.

143

The fungicidal composition generally comprises from 0.1 to 95% by weight of active ingredient, preferably from 0.5 to 90% by weight of active ingredient.

Depending on the type of effect desired, the amount used is from 0.02 to 3 kg of active substance per hectare.

In the treatment of seed, it is generally necessary to use an amount of active compound of from 0.001 to 50 g, preferably from 0.01 to 10 g, for each kilogram of seed.

The composition according to the invention may also be in a form intended for use as a fungicidal composition together with other active substances, for example with herbicidal compositions, insecticidal compositions, plant growth regulators, other fungicidal compositions or also with fertilizers.

By mixing such substances with fungicidal compositions, in many cases the broadening of the spectrum of fungicidal action is achieved.

The following list of fungicidal compositions with which the compounds of this invention may be used together is intended to elucidate the combination possibilities, but is not intended to limit such possibilities.

sulfur, dithiocarbamate and its derivatives such as ferridimethyldithiocarbamate, zinc dimethyldithiocarbamate, zinc ethylenebisdithiocarbamate, manganese ethylenebisdithiocarbamate, manganese-zinc ethylenediamine bisdithiocarbamate complex, tetramethylthiurdisate di-amide, tetramethylthiurdisate zinc bisdithiocarbamate with ammonia,

N, N'-polypropylene-bis (dithiocarbamate) from incas,

N, N ' -bis polypropylene (ditiokarbamoyl) disulfide,

144 nitro derivatives, such as dinitro (1-methylheptyl) phenyl crotonate,

2-sec-butyl-4,6-dinitrophenyl-3,3-dimethyl acrylate

2-sec-butyl-4,6-dinitrophenylisopropyl carbonate, 5-nitroisophthalic acid diisopropyl ester, heterocyclic compounds such as

2-heptadecyl-2-imidazoline acetate,

2,4-dichloro-6- (o-chloroanilino) -s-triazine,

0, O-diethyl ftalimidofosfonotioát,

5-amino-l / bis (dimethylamino) phosphinyl / 3-phenyl-1,2,4-triazole,

2,3-dicyano-l, 4-dithioanthraquinone,

2-thio-1,3-dithiolo [4,5-b] quinoxaline, 1- (butylcarbamoyl) -2-benzimidazolecarbamic acid methyl ester,

2-methoxycarbonylaminobenzimidium from o1,

2- (2-furyl) benzimidazole,

2- (4-thiazolyl) benzimidazole,

N- (1,1,2,2-tetrachloroethylthio) tetrahydrophthalimide,

N-trichloromethylthio-tetrahydrophthalimide,

N-trichloromethylthio-phthalimide, N-dichlorofluoromethylthio-N ', N'-dimethyl-N-phenylsulphuric acid diamide,

5-ethoxy-3-trichloromethyl-l, 2,3-thiadiazol.

2-rodánmetyltiobenztiazol,

1,4-dichloro-2,5-dimethoxybenzene,

4- (2-chlorophenylhydrazono) -3-methyl-5-isoxazolone, pyridine-2-thio-1-oxide,

8-hydroxyquinoline or its honey sol,

2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiin,

2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathien-4,4-dioxide, 2-methyl-5,6-dihydro-4H-pyran-3-kyric acid anilide, 2-methylfuran-anilide 3-carboxylic acid, 2,5-dimethylfuran-3-carboxylic acid anilide, 2,4,5-trimethylfuran-3-carboxylic acid anilide, 2,5-dimethylfuran-3-carboxylic acid cyclohexylamide, N-cyclohexyl-N- amide methoxy-2,5-dimethyl-furan-3-carboxylic acid,

145 2-methylbenzoic acid anilide, 2-iodobenzoic acid anilide,

N-formyl-N-morpholine-2,2,2-trichloroethylacetal, piperazine-1,4-diylbis- [1- (2,2,2-trichloroethyl)] formamide, 1- (3,4-dichloroanilino) - l-formylamino-2,2-trichjlóretán,

2,6-dimethyl-N-tridecylmorpholine or its salts,

2,6-dimethyl-N-cyclododecylmorpholine or its salts,

N- / 3- (p-tert-butylphenyl) -2-methylpropyl / cis-2,6-dimethyl-morpholine,

N- / 3- (p-tert-butylphenyl) -2-methylpropyl / piperidine.

1- / 2- (2,4-dichlorophenyl) -4-ethyl-l, 3-dioxolan-2-yl-ethyl / -lH-l, 2,4-triazole,

1- / 2- (2,4-dichlorophenyl) -4-n-propyl-l, 3-dioxolan-2-yl-ethyl / -lH-1,2,4-triazole,

N- (n-propyl) -N- (2,4,6-trichlórfenoxyetyl) -N-imidazolylmočovina,

1- (4-chlorophenoxy) -3,3-dimethyl-1- (1H-1,2,4-triazol-1-yl) -2-butanone, α- (2-chlorophenyl) -a- (4- chlorophenyl) -5-pyrimidine-methanol,

5-butyl-2-dimethylamino-4-hydroxy-6-methylpyrimidine, bis- (p-chlorophenyl) -3-pyridinemethanol,

1,2-bis- (3-ethoxycarbonyl-2-thioureido) benzene,

1,2-bis- (3-methoxycarbonyl-2-thioureido) benzene, as well as various fugicides such as dodecylguanidine acetate,

3- / 3- (3,5-dimethyl-2-oxycyclohexyl) -2-hydrooxyethyl / glutarimide, hexachlorobenzene,

DL-methyl-N- (2,6-dimethylphenyl) -N- (2-furoyl) alaninate, DL-N- (2,6-dimethylphenyl) -N- (2'-methoxyacetyl) -alanine methyl ester, N- ( 2,6-dimethylphenyl) -N-chloroacetyl-D, L-2-aminobutyrolactone, DL-N- (2,6-dimethylphenyl) -N- (phenylacetyl) alanine methyl ester, 5-methyl-5-vinyl-3- ( 3,5-dichloro-phenyl) -2,4-dioxo-l, 3-oxazolidine,

3- / 3,5-Dichlorophenyl- (5-methyl-5-methoxymethyl) / - l, 3-oxazolidin-2,4-dione

3- (3,5-dichlorophenyl) -1-isopropylcarbamoylhydantoin, N- (3,5-dichlorophenyl) -1,2-dimethylcyclopropane-1,2-dicarboxylic acid imide,

146

2-cyano- / N- (ethylaminocarbonyl) -2-methoxyimino / acetamide,

1- / 2- (2,4-dichlorophenyl) pentyl / -lH-l, 2,4-triazole,

2,4-Difluoro-α- (1H-1,2,4-triazolyl-1-methyl) benzhydryl alcohol, N- (3-chloro-2,6-dinitro-4-trifluoromethylphenyl) -5-trifluoromethyl-3-chloro -2-aminopyridine a

1 - [/ bis / (4-fluorophenyl) methylsilyl / methyl] -1H-1,2,4-triazole.

Examples of use

2- [Methoxyimino-O - [(trifluoromethyl) phenylmethyl] phenylglyoxylic acid methyl ester-O-methyloxime (Compound A) and 2- [Methoxyimino-0 - / (3-bromo) methyl ester-O-methyloxime are used as comparative active substances. -phenylmethyl] phenylglyoxyl (compound B).

Both of these compounds are known from European patent specification no. 499 823.

Example of use 1

Effect against grapevine perenospore (Plasmopara viticola)

The vine leaves of the Muller Thurgau variety, which are grown in pots, are sprayed with an aqueous spray suspension containing, in dry matter, 80% by weight of active ingredient and 20% by weight of emulsifiers. In order to assess the duration of action of the active substances, the plants are placed in a greenhouse after drying the spray layer for 8 days. Only then the leaves are infected with a zoospore suspension of vine perenospora (Plasmopara viticola). The vine plants are first placed in a water-saturated chamber at 24 ° C for 48 hours and then placed in a greenhouse for 5 days at 20-30 ° C. After this time, the plants are again placed in a humid chamber for 16 hours to induce growth of sporangia carriers. The degree of fungal infestation on the undersides of the leaves is then assessed.

147

In this experiment, plants treated with 16 ppm of the compounds (of the table / number) 1/32, 1/34, 1/49, 1/58, 1/114, 1/128, 1/134, 1/145 and 1/155 are infested with 15% or less, while 70% of the undersides of leaves are infested with untreated plants.In this test, fungi treated with preparations of known substances A and B, which are contained in an amount of 16 ppm, infect with 35% .

Application example 2

Effect against Pyrenophora teres

Young Igri wheat plants are sprayed at the two-leaf stage with aqueous suspensions containing 80% of active ingredient and 20% of emulsifier in the dry state until drips are dripped. After 24 hours, the plants are inoculated with a spore suspension of Pyrenophora teres and then placed in an air-conditioned chamber at high humidity and -18 ° C. Thereafter, the plants are cultivated in a greenhouse at 20-22 ° C and 70% RH for a further 5 days for cultivation. After this time, the degree of development of the fungal infestation symptoms is determined.

The results of this test show that the active substances Nos. 49 and 58 of Table 1 show a better fungicidal effect (leaf infestation of 5 or 15%) than the known comparative active substances A and B (leaf infestation) when applied as a spray suspension containing 63 or 16 ppm. %).

Application example 3

Action against Fusarium culmorum on wheat

Kanzler wheat, in the first leaf stage, which is planted in pots, is sprayed with a sprayed aqueous suspension which contains 80% of active ingredient and 20% of emulsifier in the dry matter until the droplets drip. The following day, the plants are inoculated with a spore suspension of Fusarium culmorum and then the test plants are kept in a climate chamber at a temperature of 20-24 ° C and high air humidity (greater than 90%).

After six days, the extent of the symptoms of action is visually evaluated.

In this experiment, plants treated with 500 ppm of compounds (from table / number) 1/8, 1/23, 1/28, 1/29, 1/32, 1/34,

1/35, 1/36, 1/37, 1/58, 1/71, 1/83, 1/114 and 1/128 are attacked by% or less, while for untreated plants 80% are attacked. In this test, fungi treated with preparations of known substances A and B, which are contained in an amount of 500 ppm, attack at 80% or 60%.

First

149

PATENT CLAIMS

Claims (11)

Compounds of formula (I) (/ (I) wherein the substituents have the following meanings: is oxygen or a group NR ^6, Ί 7 Z ^x and Z are, independently of one another, an alkenyl alkoxy group, a hydrogen atom, a halogen atom, an alkynyl alkenyloxy group, a haloalkyl group, a haloalkoxy group, a haloalkenyloxy group, a cyano group or a nitro group, R ¹ is H, alkyl, haloalkyl or aryl, R represents a hydrogen atom or an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heteroarylalkyl, heterocyclyl, cycloalkenyl, aralkyl, aryl, heteroaryl, arylalkenyl, arylalkenyl, heteroarylalkenyl, heteroarylalkenyl, heteroarylalkenyl, heteroarylalkenyl, heteroarylalkenyl, a heteroarylcarbonyl group or an alkoxycarbonyl group, 150 R ³ , R ⁴ , R ⁵ and R ⁶ are each independently hydrogen or alkyl or R ⁶ and R ² together with the nitrogen atom of which they are substituents may be a ring. A fungicidal composition comprising an inert carrier and a fungicidally effective amount of a compound of formula I according to claim 1. A fungal control method, characterized in that the materials, plants, seed or soil endangered by fungi or fungal attack are treated with a fungicidally effective amount of a compound of the formula I according to claim 1. A process for the preparation of compounds of formula I according to claim 1 1, characterized in that the ester of the general formula (II) (II) is present in an ester R is an alkyl group, reacted with an amine of formula III (III) or ammonia. 151 A process for the preparation of compounds of formula I in which R ⁵ is a hydrogen atom according to claim 1, characterized in that the mixture of a cyclic semi-amine of formula VI and a carbonyl compound of formula VII R ⁴ ' ^N ' H (VII) is reacted with a hydroxylamine derivative or a hydrazine derivative of formula VIII R ² - Y - NH ₂ (VIII) wherein Y is oxygen or a group NR ^6, or an acid addition salt thereof. A compound of formula VI according to claim 5. A process for the preparation of a compound of formula VI according to claim 5, characterized in that the ester of formula IV 152 R ³ (IV), in which R ⁷ represents an alkyl group, reacted with a primary amine of formula V H ₂ N - R ^{4 at} (V). A process for the preparation of a compound of the formula VI in which R ¹ is a hydrogen atom according to claim 5, characterized in that the α-alkoximinophenylacetic acid alkyl amide of the formula X in which: ABOUT R is an alkyl group, converted to a metal product containing two metal residues, and the metal product is reacted with a carboxylic acid derivative of formula XII 153 (XII) in which a chlorine atom, OCOR ⁷ or 7 represents OR, wherein R ⁷ represents an alkyl group or an aryl group. 9th Process for the preparation of the compounds of the general formula VI according to claim 1 5. A process according to claim 5, wherein the monoalkylamide of an alpha-alkoximinophenylacetic acid according to claim 7, wherein R @ ³ is an alkyl group, is converted to a metal product containing two metal residues. X R ¹ - (XIII) (XIII), and the resulting carbinol of formula XIV HO R ¹ -CH = U (xiv) is oxidized. - 154 10th Compound of formula (X) according to claim wherein R ³ and R ⁴ represent an alkyl group. A compound of formula XIV according to claim wherein R ³ and R ⁴ are alkyl and R ¹ is as defined in claim 1.